Supporting Information 1,3,5-Triazapentadienes by Nucleophilic Addition to 1,3- and 1,4-Dinitriles - Sterically Constrained Examples by Incorporation into Cyclic Peripheries: Synthesis, Aggregation and Photophysical Properties Agnes Johanna Wrobel, Ralph Lucchesi, Birgit Wibbeling, Constantin- Gabriel Daniliuc, Roland Fröhlich, Ernst-Ulrich Würthwein* Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, D-48149 Münster, Germany S1
Table of contents 1. X-Ray Crystal Structure Analyses S3 2. Experimental Absorption and Emission Spectra with calculated Absorption Spectra for comparison (see also below) S16 3. 1 H and 13 C NMR Spectra S20 4. Quantum Chemical Calculations S38 a) M062x/6-311++G(d,p) + GD3 Geometry Optimizations S38 b) TD-CAM-B3LYP/6-311+G(d,p) - Geometry Optimizations S52 c) Calculated Excitations (only the 10 longest wavelength excitations are shown) S61 d) Orbitalplots (TD-CAM-B3LYP/6-311+G(d,p) with orbital numbering and energies (ev) S76 S2
X-Ray Crystal Structure Analyses X-Ray diffraction: Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: data collection, COLLECT (R. W. W. Hooft, Bruker AXS, 2008, Delft, The Netherlands); data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); absorption correction, Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. 2003, A59, 228-234); structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. 1990, A46, 467-473); structure refinement SHELXL-97 (G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122) and graphics, XP (BrukerAXS, 2000) and Schakal 97 (E. Keller, Freiburg). R-values are given for observed reflections, and wr 2 values are given for all reflections. Exceptions and special features: One disordered over two positions acetone molecule was found in the asymmetrical unit of compound 11c. Several restraints (SADI, SAME, ISOR and SIMU) were used in order to improve refinement stability. For compound 12c a partial disordered five membered ring over two positions was found in the asymmetrical unit. Several restraints (SADI, SAME, ISOR and SIMU) were used in order to improve refinement stability. X-ray crystal structure analysis of 8: formula C 14 H 8 N 2, M = 204.22, pale yellow crystal, 0.25 x 0.10 x 0.08 mm, a = 15.8339(4), b = 3.9749(1), c = 16.9483(4) Å, β = 101.628(1), V = 1044.8(1) Å 3, ρ calc = 1.298 gcm -3, μ = 0.616 mm -1, empirical absorption correction (0.861 T 0.952), Z = 4, monoclinic, space group C2/c (No. 15), λ = 1.54178 Å, T = 223(2) K, ω and φ scans, 2543 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 857 independent (R int = 0.033) and 746 observed reflections [I>2σ(I)], 73 refined parameters, R = 0.042, wr 2 = 0.115, max. (min.) residual electron density 0.10 (-0.13) e.å -3, hydrogen atoms calculated and refined as riding atoms. Figure S1. ORTEP diagram of 8 with ellipsoids shown at the 30% probability level. S3
X-ray crystal structure analysis of 10a: formula C 18 H 13 N 3, M = 271.31, red crystal, 0.25 x 0.20 x 0.15 mm, a = 12.3812(3), b = 5.6553(1), c = 18.7769(5) Å, β = 92.864(1), V = 1313.1(1) Å 3, ρ calc = 1.372 gcm -3, μ = 0.083 mm -1, empirical absorption correction (0.979 T 0.987), Z = 4, monoclinic, space group P2 1 /n (No. 14), λ = 0.71073 Å, T = 223(2) K, ω and φ scans, 10080 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 2664 independent (R int = 0.050) and 1938 observed reflections [I>2σ(I)], 198 refined parameters, R = 0.045, wr 2 = 0.126, max. (min.) residual electron density 0.16 (-0.21) e.å -3, the hydrogen atoms at N2 were refined freely; others were calculated and refined as riding atoms. Figure S2. ORTEP diagram of 10a with ellipsoids shown at the 30% probability level. S4
X-ray crystal structure analysis of 10b: formula C 19 H 15 N 3, M = 285.34, yellow crystal, 0.35 x 0.05 x 0.03 mm, a = 5.3908(4), b = 12.7036(8), c = 21.4042(16) Å, β = 92.502(3), V = 1464.4(2) Å 3, ρ calc = 1.294 gcm -3, μ = 0.611 mm -1, empirical absorption correction (0.814 T 0.981), Z = 4, monoclinic, space group P2 1 /c (No. 14), λ = 1.54178 Å, T = 223(2) K, ω and φ scans, 9119 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 2460 independent (R int = 0.066) and 1610 observed reflections [I>2σ(I)], 208 refined parameters, R = 0.053, wr 2 = 0.148, max. (min.) residual electron density 0.16 (-0.16) e.å -3, the hydrogen atoms at N2 were refined freely, but with N-H distance restraint (SADI); others were calculated and refined as riding atoms. Figure S3. ORTEP diagram of 10b with ellipsoids shown at the 30% probability level. S5
X-ray crystal structure analysis of 10c: formula C 17 H 12 N 4, M = 272.31, yellow crystal, 0.25 x 0.10 x 0.07 mm, a = 14.5287(1), b = 5.1310(1), c = 18.0984(1) Å, β = 106.735(1), V = 1292.0(1) Å 3, ρ calc = 1.400 gcm -3, μ = 0.690 mm -1, empirical absorption correction (0.846 T 0.953), Z = 4, monoclinic, space group P2 1 /c (No. 14), λ = 1.54178 Å, T = 223(2) K, ω and φ scans, 8735 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 2213 independent (R int = 0.049) and 1744 observed reflections [I>2σ(I)], 198 refined parameters, R = 0.042, wr 2 = 0.120, max. (min.) residual electron density 0.14 (-0.16) e.å -3, the hydrogen atoms at N1 and N2 were refined freely; others were calculated and refined as riding atoms. Figure S4. ORTEP diagram of 10c with ellipsoids shown at the 30% probability level. S6
X-ray crystal structure analysis of 11b: formula C 19 H 14 N 4 ٠ H 2 O, M = 316.36, colourless crystal, 0.20 x 0.12 x 0.03 mm, a = 21.9750(5), b = 7.9493(2), c = 19.2418(6) Å, β = 104.993(1), V = 3246.8(2) Å 3, ρ calc = 1.294 gcm -3, μ = 0.084 mm -1, empirical absorption correction (0.983 T 0.997), Z = 8, monoclinic, space group C2/c (No. 15), λ = 0.71073 Å, T = 223(2) K, ω and φ scans, 15235 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 3250 independent (R int = 0.078) and 2299 observed reflections [I>2σ(I)], 233 refined parameters, R = 0.063, wr 2 = 0.152, max. (min.) residual electron density 0.22 (-0.20) e.å -3, the hydrogen atoms at O1 and N2 were refined freely; others were calculated and refined as riding atoms. Figure S5. ORTEP diagram of 11b with ellipsoids shown at the 30% probability level. S7
X-ray crystal structure analysis of 11c: formula C 16 H 16 N 4 ٠ 0.5 x C 3 H 6 O, M = 293.37, colourless crystal, 0.25 x 0.12 x 0.07 mm, a = 22.1401(7), b = 10.4147(4), c = 14.3555(7) Å, β = 100.699(3), V = 3252.6(2) Å 3, ρ calc = 1.198 gcm -3, μ = 0.598 mm -1, empirical absorption correction (0.865 T 0.959), Z = 8, monoclinic, space group Cc (No. 9), λ = 1.54178 Å, T = 223(2) K, ω and φ scans, 12092 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 5061 independent (R int = 0.040) and 4829 observed reflections [I>2σ(I)], 456 refined parameters, R = 0.038, wr 2 = 0.097, max. (min.) residual electron density 0.40 (-0.12) e.å -3, the hydrogen atoms at N2A and N2B were refined freely; others were calculated and refined as riding atoms. Figure S6. ORTEP diagram of 11c with ellipsoids shown at the 30% probability level. S8
X-ray crystal structure analysis of 12a: formula C 20 H 23 N 3, M = 305.41, yellow crystal, 0.35 x 0.15 x 0.08 mm, a = 11.7471(1), b = 13.2910(1), c = 11.5874(1) Å, β = 106.749(1), V = 1732.4(2) Å 3, ρ calc = 1.171 gcm -3, μ = 0.538 mm -1, empirical absorption correction (0.833 T 0.958), Z = 4, monoclinic, space group P2 1 /n (No. 14), λ = 1.54178 Å, T = 223(2) K, ω and φ scans, 12731 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 3030 independent (R int = 0.039) and 2749 observed reflections [I>2σ(I)], 219 refined parameters, R = 0.044, wr 2 = 0.115, max. (min.) residual electron density 0.22 (-0.19) e.å -3, the hydrogen atoms at N2 were refined freely; others were calculated and refined as riding atoms. Figure S7. ORTEP diagram of 12a with ellipsoids shown at the 30% probability level. S9
X-ray crystal structure analysis of 12b: formula C 15 H 22 N 4, M = 258.37, colourless crystal, 0.20 x 0.10 x 0.07 mm, a = 17.2832(9), b = 10.5241(5), c = 16.7531(8) Å, β = 102.000(5), V = 2980.6(3) Å 3, ρ calc = 1.152 gcm -3, μ = 0.552 mm -1, empirical absorption correction (0.897 T 0.962), Z = 8, monoclinic, space group C2/c (No. 15), λ = 1.54178 Å, T = 223(2) K, ω and φ scans, 16158 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 2598 independent (R int = 0.047) and 2205 observed reflections [I>2σ(I)], 185 refined parameters, R = 0.042, wr 2 = 0.116, max. (min.) residual electron density 0.14 (-0.13) e.å -3, the hydrogen atoms at N2 were refined freely; others were calculated and refined as riding atoms. Figure S8. ORTEP diagram of 12b with ellipsoids shown at the 30% probability level. S10
X-ray crystal structure analysis of 12c: formula C 20 H 21 N 3 ٠ 2 x 0.5 C 7 H 8, M = 395.53, pale yellow crystal, 0.40 x 0.15 x 0.12 mm, a = 9.3920(5), b = 9.6342(5), c = 13.7713(8) Å, α = 77.113(2), β = 81.781(2), γ = 65.015(2), V = 1099.3(1) Å 3, ρ calc = 1.195 gcm -3, μ = 0.539 mm -1, empirical absorption correction (0.947 T 0.977), Z = 2, triclinic, space group P1 (No. 2), λ = 1.54178 Å, T = 223(2) K, ω and φ scans, 13243 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 3817 independent (R int = 0.041) and 3281 observed reflections [I>2σ(I)], 331 refined parameters, R = 0.053, wr 2 = 0.149, max. (min.) residual electron density 0.27 (- 0.24) e.å -3, the hydrogen atoms at N2 were refined freely, but with N-H distance restraint (SADI); others were calculated and refined as riding atoms. Figure S9. ORTEP diagram of 12c with ellipsoids shown at the 30% probability level. S11
X-ray crystal structure analysis of 12d: formula C 20 H 22 N 4, M = 318.42, yellow crystal, 0.30 x 0.30 x 0.10 mm, a = 16.8777(4), b = 9.1711(2), c = 21.9473(6) Å, β = 91.346(1), V = 3396.2(2) Å 3, ρ calc = 1.245 gcm -3, μ = 0.076 mm -1, empirical absorption correction (0.977 T 0.992), Z = 8, monoclinic, space group C2/c (No. 15), λ = 0.71073 Å, T = 223(2) K, ω and φ scans, 7944 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 2836 independent (R int = 0.041) and 2543 observed reflections [I>2σ(I)], 226 refined parameters, R = 0.051, wr 2 = 0.125, max. (min.) residual electron density 0.14 (-0.14) e.å -3, the hydrogen atoms at N2 were refined freely; others were calculated and refined as riding atoms. Figure S10. ORTEP diagram of 12d with ellipsoids shown at the 30% probability level. S12
X-ray crystal structure analysis of 12e: formula C 18 H 18 N 4 ٠ C 3 H 6 O, M = 348.44, pale yellow crystal, 0.20 x 0.20 x 0.15 mm, a = 13.1740(6), b = 9.6470(4), c = 16.3830(7) Å, β = 113.416(2), V = 1910.6(2) Å 3, ρ calc = 1.211 gcm -3, μ = 0.607 mm -1, empirical absorption correction (0.888 T 0.914), Z = 4, monoclinic, space group P2 1 /c (No. 14), λ = 1.54178 Å, T = 223(2) K, ω and φ scans, 13798 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 3369 independent (R int = 0.040) and 2990 observed reflections [I>2σ(I)], 245 refined parameters, R = 0.047, wr 2 = 0.129, max. (min.) residual electron density 0.31 (-0.20) e.å -3, the hydrogen atoms at N2 were refined freely; others were calculated and refined as riding atoms. Figure S11. ORTEP diagram of 12e with ellipsoids shown at the 30% probability level. S13
X-ray crystal structure analysis of 12f: formula C 17 H 23 N 3, M = 269.38, yellow crystal, 0.50 x 0.40 x 0.20 mm, a = 9.0878(1), b = 9.2020(1), c = 9.5148(2) Å, α = 95.924(1), β = 110.639(1), γ = 96.782(1), V = 730.3(2) Å 3, ρ calc = 1.225 gcm -3, μ = 0.565 mm -1, empirical absorption correction (0.765 T 0.895), Z = 2, triclinic, space group P 1 (No. 2), λ = 1.54178 Å, T = 223(2) K, ω and φ scans, 8996 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 2546 independent (R int = 0.033) and 2422 observed reflections [I>2σ(I)], 187 refined parameters, R = 0.041, wr 2 = 0.106, max. (min.) residual electron density 0.19 (-0.16) e.å -3, the hydrogen atoms at N2 were refined freely; others were calculated and refined as riding atoms. Figure S12. ORTEP diagram of 12f with ellipsoids shown at the 30% probability level. S14
X-ray crystal structure analysis of 13: formula C 13 H 14 N 2 O, M = 214.26, colourless crystal, 0.35 x 0.25 x 0.03 mm, a = 15.6020(4), b = 12.9520(3), c = 11.0992(2) Å, β = 103.310(1), V = 2182.6(1) Å 3, ρ calc = 1.304 gcm -3, μ = 0.084 mm -1, empirical absorption correction (0.971 T 0.997), Z = 8, monoclinic, space group C2/c (No. 15), λ = 0.71073 Å, T = 223(2) K, ω and φ scans, 14393 reflections collected (±h, ±k, ±l), [(sin )/λ] = 0.60 Å -1, 2540 independent (R int = 0.055) and 1961 observed reflections [I>2σ(I)], 157 refined parameters, R = 0.060, wr 2 = 0.139, max. (min.) residual electron density 0.24 (-0.17) e.å -3, the hydrogen atoms at N2 were refined freely; others were calculated and refined as riding atoms. Figure S13. ORTEP diagram of 13 with ellipsoids shown at the 30% probability level. S15
Experimental Absorption and Emission Spectra with calculated Absorption Spectra for comparison (see also pages S60 ff) Norm. Absorption / Norm. Emission 1,0 0,8 0,6 0,4 0,2 0,0 200 400 600 800 Wavelength (nm) Figure S14. Experimental UV/Vis- and fluorescence spectrum of 10a. Monomer Dimer Figure S15. Calculated UV/Vis spectra for the monomer (top) and the dimer (bottom) of 10a. S16
Figure S16. Experimental UV/Vis- and fluorescence spectrum of 10b. Monomer Dimer Figure S17. Calculated UV/Vis spectra for the monomer (top) and the dimer (bottom) of 10b. S17
Figure S18. Experimental UV/Vis- and fluorescence spectrum of 10c. Figure S19. Calculated UV/Vis spectrum of 10c. S18
Figure S20. Experimental UV/Vis- and fluorescence spectrum of 12d. Monomer Dimer Figure S21. Calculated UV/Vis spectra for the monomer (top) and the dimer (bottom) of 12d. S19
1 H and 13 C NMR Spectra 7 Figure S22: 1 H (Top; 300 MHz) in d 6 -DMSO and 13 C { 1 H} NMR (bottom, 100 MHz) spectra of compound 7 in CDCl 3. S20
9a Figure S23: 1 H (Top; 400 MHz) and 13 C { 1 H} NMR (bottom, 100 MHz) spectra of compound 9a in CDCl 3. S21
9b Figure S24: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 9b in CDCl 3. S22
10a Figure S25: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 10a in d 6 -DMSO. S23
10b Figure S26: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 10b in d 6 -DMSO. S24
10c Figure S27: 1 H (Top; 400 MHz) and 13 C { 1 H} NMR (bottom, 100 MHz) spectra of compound 10c in d 6 -DMSO. S25
10d Figure S28: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 10d in CDCl 3 (The compound is quite sensitive, showing impurities in the spectra). S26
10e Figure S29: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 10e in d 6 -DMSO 3. S27
11a Figure S30: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 11a in d 6 -DMSO. S28
11b Figure S31: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 11b in d 6 -DMSO. S29
11c Figure S32: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 11c in CDCl 3. S30
12a Figure S33: 1 H (Top; 400 MHz) and 13 C { 1 H} NMR (bottom, 150 MHz) spectra of compound 12a in CDCl 3. S31
12b Figure S34: 1 H (Top; 400 MHz) and 13 C { 1 H} NMR (bottom, 100 MHz) spectra of compound 12b in CDCl 3. S32
12c Figure S35: 1 H (Top; 400 MHz) and 13 C { 1 H} NMR (bottom, 100 MHz) spectra of compound 12c in d 6 -DMSO. S33
12d Figure S36: 1 H (Top; 400 MHz) and 13 C { 1 H} NMR (bottom, 100 MHz) spectra of compound 12d in CDCl 3. S34
12e Figure S37: 1 H (Top; 400 MHz) and 13 C { 1 H} NMR (bottom, 100 MHz) spectra of compound 12e in CDCl 3. S35
12f Figure S38: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 12f in CDCl 3. S36
14 Figure S39: 1 H (Top; 300 MHz) and 13 C { 1 H} NMR (bottom, 75 MHz) spectra of compound 14 in d 6 -DMSO. S37
Quantum Chemical Calculations 1,2,3 Results from Gaussian09-Outputs (Coordinates, Total energies (a.u.), Number of imaginary frequencies) a) M062x/6-311++G(d,p) + GD3 Geometry Optimizations 2-(1-Cyano-cyclopentyl)-benzonitrile 9b E tot = -611.9917825 a.u. (0) Element x y z NBO-Charge 6 1.253122-1.687366 0.147267-0.20114 6 2.633895-1.853685 0.085548-0.16999 6 3.466710-0.757885-0.093430-0.20303 6 2.910384 0.508045-0.203896-0.14094 6 1.525401 0.673208-0.141708-0.17271 6 0.668419-0.429395 0.027717 0.02681 6-0.845296-0.251337 0.086012-0.19032 6 (benzylic) -1.185442 0.591619 1.248630 0.29473 6 (aromatic) 1.019272 2.015476-0.250604 0.27865 7 0.650513 3.099708-0.357028-0.29145 6-1.466853 0.365588-1.197441-0.37043 6-2.975972 0.098339-1.056925-0.40257 6-3.106593-1.118735-0.102923-0.40029 6-1.666412-1.555787 0.199466-0.37246 7-1.481198 1.219541 2.164671-0.31273 1 0.628861-2.556872 0.303206 0.22173 1 3.055506-2.846756 0.185444 0.21738 1 4.541103-0.883718-0.139682 0.22123 1 3.537425 1.381187-0.335134 0.22891 1-1.231400 1.420400-1.321292 0.23940 1-1.044467-0.184059-2.043734 0.20864 1-3.430746-0.086191-2.030365 0.21321 1-3.470816 0.970333-0.627338 0.21714 1-3.607630-0.822541 0.820059 0.21600 1-3.682345-1.934876-0.539518 0.21288 1-1.310814-2.235508-0.579865 0.20710 1-1.553696-2.044657 1.168440 0.22422 Z-2-Aminopyridine anion E tot = -303.0153343 a.u. (0) Element x y z NBO-Charge 6-0.967349-1.210736 0.000038 0.06241 6-1.803086-0.097097 0.000045-0.43767 6-1.155550 1.158020 0.000045-0.19993 6 0.209511 1.228294-0.000044-0.31839 6 1.020512 0.022642-0.000277 0.37589 7 (pyridyl) 0.357524-1.200428-0.000070-0.62418 S38
7 (amine) 2.328003 0.113032 0.000150-0.87044 1-1.420763-2.205439 0.000071 0.14967 1-2.880524-0.199834 0.000102 0.18629 1-1.741984 2.074650 0.000120 0.17696 1 0.733496 2.177231 0.000022 0.19350 1 2.686851-0.841570 0.000275 0.30589 Aniline-anion E tot = -286.9575914 a.u. (0) Element x y z NBO-Charge 6-0.296259 1.193169-0.000712-0.34419 6 1.087376 1.212163 0.000218-0.21143 6 1.845649 0.035617 0.000143-0.38890 6 1.137299-1.177947 0.000162-0.21492 6-0.241010-1.223298-0.000617-0.30528 6-1.060212-0.033826 0.000033 0.17948 1 2.928831 0.059241 0.001261 0.18056 7-2.381535-0.131692 0.000537-0.89190 1-2.772412 0.811031 0.000631 0.28605 1 1.596421 2.174515 0.000041 0.17462 1 1.690481-2.115424 0.000011 0.17525 1-0.763442-2.175022-0.000518 0.18835 1-0.846196 2.132233-0.000551 0.17232 10b-monomer E tot = -897.195689 a.u. (0) 1 7 0-0.717865 3.092365-0.464134 2 1 0-1.461168 3.632786-0.873558 3 1 0 0.219873 3.352649-0.733126 4 6 0-0.895132 1.749550-0.277094 5 7 0 0.158631 1.006385-0.254519 6 6 0 0.054201-0.369506-0.080669 7 7 0 1.072663-1.142319-0.002956 8 6 0 2.387521-0.655499 0.028039 9 6 0 2.806369 0.401761 0.845753 10 1 0 2.078862 0.919150 1.457150 11 6 0 4.142806 0.770248 0.882495 12 1 0 4.450227 1.586002 1.529976 13 6 0 5.102030 0.118184 0.103881 14 6 0 4.677951-0.934914-0.704821 15 1 0 5.402637-1.464192-1.315149 16 6 0 3.346851-1.331998-0.728598 17 1 0 3.027600-2.167825-1.340131 18 6 0 6.552402 0.522048 0.170696 19 1 0 7.008647 0.185244 1.105952 20 1 0 6.662398 1.607781 0.123629 21 1 0 7.120084 0.086396-0.652912 S39
22 6 0-1.293564-0.996988-0.035489 23 6 0-1.461040-2.362407 0.031666 24 1 0-0.578486-2.989951 0.023765 25 6 0-2.749711-2.924031 0.120305 26 1 0-2.857372-4.001169 0.166882 27 6 0-3.862761-2.121111 0.160644 28 1 0-4.854697-2.551849 0.243734 29 6 0-3.729887-0.713370 0.101298 30 6 0-4.844917 0.161061 0.166771 31 1 0-5.838261-0.264888 0.259774 32 6 0-4.673123 1.520014 0.127897 33 1 0-5.528734 2.180616 0.194844 34 6 0-3.380077 2.073000 0.000514 35 1 0-3.276425 3.151664-0.004144 36 6 0-2.276256 1.255442-0.087982 37 6 0-2.431860-0.154389-0.014545 10b-dimer E tot = -1794.4407169 a.u. (0) 1 7 0 1.280418-1.146273 0.665044 2 1 0 1.623615-2.094521 0.653813 3 1 0 0.285048-1.040587 0.445299 4 6 0 2.112574-0.123833 0.449580 5 7 0 1.598118 1.057833 0.215522 6 6 0 2.408596 2.155211-0.012065 7 7 0 1.951868 3.349301-0.136047 8 6 0 0.598498 3.632429 0.085568 9 6 0-0.035908 3.356490 1.305267 10 1 0 0.520887 2.849424 2.084075 11 6 0-1.361017 3.712755 1.507037 12 1 0-1.834343 3.483059 2.456718 13 6 0-2.106959 4.347568 0.508075 14 6 0-1.465983 4.630303-0.699471 15 1 0-2.014917 5.132115-1.490867 16 6 0-0.130370 4.294105-0.905727 17 1 0 0.361241 4.526419-1.843008 18 6 0-3.544709 4.733229 0.747803 19 1 0-3.609922 5.620180 1.384155 20 1 0-4.091009 3.927585 1.244734 21 1 0-4.053624 4.962167-0.191122 22 6 0 3.877183 1.966022-0.154396 23 6 0 4.711996 3.001749-0.507237 24 1 0 4.273333 3.971114-0.709216 25 6 0 6.104487 2.804055-0.591586 26 1 0 6.742201 3.632228-0.876597 27 6 0 6.654335 1.579433-0.305995 28 1 0 7.726922 1.427289-0.358868 29 6 0 5.826946 0.492595 0.067051 30 6 0 6.349404-0.785363 0.389913 31 1 0 7.422467-0.938315 0.346935 S40
32 6 0 5.515005-1.808078 0.758121 33 1 0 5.920616-2.780020 1.012007 34 6 0 4.117977-1.610635 0.805802 35 1 0 3.492164-2.444416 1.102948 36 6 0 3.572625-0.387590 0.486572 37 6 0 4.424000 0.690716 0.128028 38 7 0-1.280443 1.146285-0.665135 39 1 0-1.623612 2.094544-0.653895 40 1 0-0.285061 1.040582-0.445435 41 6 0-2.112609 0.123857-0.449644 42 7 0-1.598152-1.057816-0.215641 43 6 0-2.408613-2.155216 0.011892 44 7 0-1.951858-3.349291 0.135948 45 6 0-0.598464-3.632395-0.085559 46 6 0 0.036034-3.356400-1.305205 47 1 0-0.520709-2.849299-2.084026 48 6 0 1.361142-3.712681-1.506908 49 1 0 1.834534-3.482945-2.456546 50 6 0 2.107009-4.347578-0.507937 51 6 0 1.465947-4.630376 0.699542 52 1 0 2.014805-5.132275 1.490936 53 6 0 0.130324-4.294149 0.905736 54 1 0-0.361357-4.526534 1.842963 55 6 0 3.544770-4.733231-0.747607 56 1 0 3.610035-5.619905-1.384338 57 1 0 4.091197-3.927402-1.244104 58 1 0 4.053528-4.962601 0.191296 59 6 0-3.877189-1.966036 0.154286 60 6 0-4.711985-3.001783 0.507118 61 1 0-4.273302-3.971149 0.709049 62 6 0-6.104474-2.804106 0.591506 63 1 0-6.742174-3.632294 0.876505 64 6 0-6.654338-1.579477 0.305974 65 1 0-7.726924-1.427341 0.358880 66 6 0-5.826967-0.492618-0.067052 67 6 0-6.349447 0.785352-0.389832 68 1 0-7.422511 0.938289-0.346822 69 6 0-5.515067 1.808096-0.758004 70 1 0-5.920697 2.780050-1.011814 71 6 0-4.118041 1.610665-0.805743 72 1 0-3.492245 2.444464-1.102875 73 6 0-3.572665 0.387607-0.486595 74 6 0-4.424021-0.690723-0.128076 11c-monomer E tot =.-838.1811491 a.u. (0) 1 6 0 1.202949-1.225178 0.388842 2 6 0 1.629902-0.054178-0.263848 3 6 0 1.054581 1.288805-0.001974 4 6 0-0.324659 1.480587 0.165976 S41
5 6 0-1.249577 0.316744 0.253229 6 7 0 0.276023-2.065426 2.461764 7 1 0-0.418013-1.964386 3.188670 8 1 0 1.219521-2.229751 2.776184 9 7 0-1.002164-0.581685 1.290627 10 7 0-2.295343 0.335850-0.478130 11 7 0-3.219187-0.700790-0.349870 12 6 0 0.103581-1.211838 1.394356 13 6 0 2.659242-0.169626-1.207802 14 1 0 2.975811 0.716948-1.743977 15 6 0 3.251285-1.389658-1.495818 16 1 0 4.034733-1.444801-2.242380 17 6 0 2.826308-2.540688-0.840550 18 1 0 3.273989-3.500643-1.066974 19 6 0 1.810484-2.451535 0.098362 20 1 0 1.457097-3.343024 0.602999 21 6 0 1.891830 2.411522-0.003346 22 1 0 2.962628 2.273731-0.101104 23 6 0 1.374641 3.690907 0.137931 24 1 0 2.042389 4.544087 0.146748 25 6 0 0.000587 3.873146 0.268652 26 1 0-0.411044 4.870423 0.369172 27 6 0-0.840773 2.770423 0.284174 28 1 0-1.912817 2.886023 0.388145 29 6 0-4.355388-0.385922-1.208440 30 1 0-4.083204-0.410198-2.273993 31 1 0-4.718995 0.610011-0.962204 32 1 0-5.149827-1.109976-1.021663 33 6 0-2.684696-2.022654-0.676788 34 1 0-1.990323-2.364315 0.085927 35 1 0-2.180109-2.011083-1.655357 36 1 0-3.518915-2.723828-0.718649 11c-monomer-TS E tot = -838.15222 a.u. (1) 1 6 0-1.637700-1.183622 0.107083 2 6 0-1.891845 0.186835-0.117989 3 6 0-0.907108 1.310316-0.014910 4 6 0 0.500144 1.246909-0.103441 5 6 0 1.333048-0.000783-0.162994 6 7 0-0.313778-3.195246-0.153115 7 1 0 0.581916-3.547579-0.462166 8 1 0-1.098950-3.623793-0.618309 9 7 0 0.861437-1.292964-0.214114 10 7 0 2.606693 0.196187-0.202912 11 7 0 3.471744-0.887909-0.237995 12 6 0-0.297247-1.807500-0.069011 13 6 0-3.229675 0.526937-0.398027 14 1 0-3.456035 1.522691-0.749242 15 6 0-4.281981-0.361347-0.256541 16 1 0-5.291116-0.036546-0.480273 S42
17 6 0-4.033367-1.650304 0.194843 18 1 0-4.841605-2.344844 0.386773 19 6 0-2.717595-2.051212 0.339339 20 1 0-2.515300-3.066596 0.652097 21 6 0-1.474836 2.575254 0.260812 22 1 0-2.529662 2.644639 0.479242 23 6 0-0.739389 3.740931 0.317678 24 1 0-1.233073 4.679937 0.537180 25 6 0 0.633640 3.681532 0.107193 26 1 0 1.240149 4.579252 0.125034 27 6 0 1.228582 2.450648-0.071469 28 1 0 2.301733 2.379502-0.167680 29 6 0 4.813726-0.373278-0.484971 30 1 0 5.178868 0.240034 0.352420 31 1 0 4.801486 0.234241-1.388361 32 1 0 5.490759-1.215896-0.634651 33 6 0 3.462746-1.700159 0.980554 34 1 0 2.493605-2.168686 1.121144 35 1 0 3.706857-1.086372 1.861153 36 1 0 4.220839-2.477392 0.873708 11c-dimer E tot = -1676.3883096 a.u. (0) 1 6 0-3.226640 1.215780-0.773085 2 6 0-4.507034 0.958678-0.254324 3 6 0-4.746002 0.188836 0.991213 4 6 0-4.027201-0.978699 1.284696 5 6 0-2.871285-1.398080 0.441227 6 7 0-0.935644 1.553557-0.113645 7 1 0-0.013243 1.256727 0.215024 8 1 0-1.039197 2.518761-0.374173 9 7 0-1.824188-0.497938 0.315480 10 7 0-2.835573-2.618783 0.060165 11 7 0-1.693602-3.021108-0.666952 12 6 0-1.981111 0.709579-0.121743 13 6 0-5.612879 1.460232-0.953387 14 1 0-6.606562 1.245745-0.578775 15 6 0-5.466639 2.187542-2.124388 16 1 0-6.344714 2.547477-2.647349 17 6 0-4.196162 2.433488-2.633803 18 1 0-4.070199 2.984857-3.557545 19 6 0-3.088055 1.949883-1.955726 20 1 0-2.094924 2.117293-2.357317 21 6 0-5.771806 0.582384 1.858134 22 1 0-6.313283 1.499401 1.656307 23 6 0-6.090021-0.170262 2.978812 24 1 0-6.878571 0.160518 3.644107 25 6 0-5.394255-1.346397 3.243945 26 1 0-5.644572-1.944565 4.112109 27 6 0-4.367965-1.744304 2.399268 S43
28 1 0-3.811375-2.654074 2.587929 29 6 0-1.755283-4.474486-0.785061 30 1 0-2.628681-4.800386-1.367853 31 1 0-1.817711-4.909551 0.211149 32 1 0-0.844354-4.830141-1.271528 33 6 0-1.648812-2.411613-1.998081 34 1 0-1.455846-1.342632-1.924114 35 1 0-2.591482-2.577800-2.539732 36 1 0-0.832954-2.871641-2.559810 37 6 0 3.226640-1.215778-0.773088 38 6 0 4.507034-0.958678-0.254326 39 6 0 4.746001-0.188839 0.991213 40 6 0 4.027200 0.978695 1.284699 41 6 0 2.871285 1.398079 0.441230 42 7 0 0.935643-1.553556-0.113648 43 1 0 1.039195-2.518760-0.374178 44 1 0 0.013243-1.256725 0.215022 45 7 0 1.824187 0.497938 0.315481 46 7 0 2.835575 2.618783 0.060170 47 7 0 1.693606 3.021112-0.666946 48 6 0 1.981111-0.709578-0.121744 49 6 0 5.612879-1.460231-0.953390 50 1 0 6.606561-1.245745-0.578777 51 6 0 5.466638-2.187536-2.124393 52 1 0 6.344713-2.547470-2.647356 53 6 0 4.196161-2.433481-2.633809 54 1 0 4.070198-2.984847-3.557553 55 6 0 3.088054-1.949877-1.955731 56 1 0 2.094923-2.117286-2.357322 57 6 0 5.771804-0.582390 1.858134 58 1 0 6.313281-1.499407 1.656305 59 6 0 6.090018 0.170253 2.978814 60 1 0 6.878568-0.160529 3.644109 61 6 0 5.394253 1.346387 3.243950 62 1 0 5.644569 1.944552 4.112115 63 6 0 4.367963 1.744297 2.399273 64 1 0 3.811374 2.654066 2.587936 65 6 0 1.755291 4.474489-0.785053 66 1 0 1.817721 4.909552 0.211158 67 1 0 2.628689 4.800388-1.367844 68 1 0 0.844363 4.830148-1.271518 69 6 0 1.648813 2.411619-1.998076 70 1 0 2.591484 2.577802-2.539726 71 1 0 1.455840 1.342639-1.924112 72 1 0 0.832959 2.871653-2.559805 12b-monomer E tot = -803.6963877 a.u. (0) 1 7 0 0.531331-2.972720-0.169282 2 1 0-0.282008-3.522812-0.400037 S44
3 1 0 1.431565-3.359120-0.393946 4 7 0-0.869241-1.201701-0.165750 5 7 0-2.337981 0.635300-0.175389 6 7 0-3.424551-0.223035-0.289674 7 6 0-1.148851 0.159756-0.106058 8 6 0 0.343776-1.619772-0.131634 9 6 0 1.616553-0.790286-0.017068 10 6 0 1.280054 0.691769 0.046786 11 6 0-0.038896 1.141371-0.001709 12 6 0-0.307950 2.515730 0.052997 13 1 0-1.341542 2.834401 0.018332 14 6 0 0.721883 3.432621 0.150929 15 1 0 0.502201 4.492956 0.190418 16 6 0 2.043359 2.987936 0.203714 17 1 0 2.857489 3.698342 0.286268 18 6 0 2.313385 1.630387 0.152071 19 1 0 3.344414 1.296709 0.194503 20 6 0 2.502950-1.064017-1.260661 21 1 0 3.396381-0.439829-1.177151 22 1 0 2.862855-2.098359-1.234352 23 6 0 1.796667-0.787785-2.585029 24 1 0 0.921330-1.431125-2.708672 25 1 0 2.468614-0.966502-3.426064 26 1 0 1.457891 0.249569-2.633678 27 6 0 2.370842-1.216374 1.268560 28 1 0 2.688046-2.258886 1.168829 29 1 0 3.286028-0.620830 1.331674 30 6 0 1.544490-1.046642 2.539390 31 1 0 1.226572-0.008668 2.661602 32 1 0 2.125685-1.330353 3.418426 33 1 0 0.649337-1.673621 2.510126 34 6 0-3.610655-1.113035 0.857087 35 1 0-2.787549-1.816874 0.927617 36 1 0-4.540947-1.663264 0.709212 37 1 0-3.686195-0.535487 1.791596 38 6 0-4.614172 0.593759-0.496022 39 1 0-4.858262 1.196558 0.391752 40 1 0-5.455253-0.061904-0.727198 41 1 0-4.444155 1.261690-1.338707 12b-dimer E tot = -1607.4340033 a.u. (0) 1 7 0-0.902612-1.508979-0.544051 2 1 0 0.044612-1.134361-0.407823 3 1 0-0.957325-2.508974-0.632760 4 7 0-1.805326 0.514284-0.110362 5 7 0-2.764701 2.640167 0.143596 6 7 0-1.472600 3.180259-0.035711 7 6 0-2.881525 1.362172 0.081910 8 6 0-1.985050-0.759085-0.316275 S45
9 6 0-3.322605-1.493031-0.341032 10 6 0-4.463598-0.556452 0.022154 11 6 0-4.250400 0.804338 0.234509 12 6 0-5.323857 1.639369 0.569339 13 1 0-5.123164 2.691489 0.723858 14 6 0-6.601976 1.125908 0.690517 15 1 0-7.426569 1.777335 0.954446 16 6 0-6.825626-0.232593 0.463859 17 1 0-7.825110-0.643294 0.546575 18 6 0-5.765422-1.059836 0.131844 19 1 0-5.956080-2.112117-0.046259 20 6 0-3.260882-2.656606 0.682844 21 1 0-4.226713-3.167582 0.673670 22 1 0-2.531470-3.399169 0.343321 23 6 0-2.923815-2.201571 2.099738 24 1 0-1.937447-1.731132 2.137829 25 1 0-2.918829-3.049478 2.787054 26 1 0-3.657793-1.476602 2.459315 27 6 0-3.544854-2.059074-1.767038 28 1 0-2.776031-2.810504-1.972817 29 1 0-4.503849-2.585364-1.771634 30 6 0-3.527909-0.989819-2.855012 31 1 0-4.297860-0.235584-2.675561 32 1 0-3.710503-1.434948-3.834529 33 1 0-2.559159-0.484067-2.892304 34 6 0-1.047213 3.080462-1.434844 35 1 0-0.922712 2.034788-1.712444 36 1 0-0.084906 3.587112-1.545304 37 1 0-1.778877 3.555194-2.104928 38 6 0-1.537675 4.580585 0.366803 39 1 0-2.234074 5.155391-0.260831 40 1 0-0.539846 5.019363 0.287418 41 1 0-1.868557 4.639145 1.402883 42 7 0 0.902634 1.508994 0.544106 43 1 0-0.044590 1.134385 0.407842 44 1 0 0.957354 2.508989 0.632806 45 7 0 1.805333-0.514268 0.110387 46 7 0 2.764682-2.640162-0.143602 47 7 0 1.472585-3.180255 0.035682 48 6 0 2.881521-1.362170-0.081895 49 6 0 1.985067 0.759095 0.316310 50 6 0 3.322629 1.493029 0.341058 51 6 0 4.463605 0.556446-0.022171 52 6 0 4.250395-0.804346-0.234509 53 6 0 5.323843-1.639385-0.569351 54 1 0 5.123144-2.691507-0.723848 55 6 0 6.601959-1.125928-0.690575 56 1 0 7.426544-1.777361-0.954516 57 6 0 6.825617 0.232577-0.463950 58 1 0 7.825100 0.643276-0.546706 59 6 0 5.765425 1.059826-0.131913 S46
60 1 0 5.956087 2.112110 0.046169 61 6 0 3.260901 2.656630-0.682789 62 1 0 4.226770 3.167537-0.673685 63 1 0 2.531573 3.399239-0.343187 64 6 0 2.923680 2.201652-2.099663 65 1 0 1.937282 1.731268-2.137676 66 1 0 2.918679 3.049578-2.786956 67 1 0 3.657584 1.476650-2.459327 68 6 0 3.544918 2.059037 1.767071 69 1 0 2.776085 2.810444 1.972897 70 1 0 4.503902 2.585347 1.771649 71 6 0 3.528036 0.989750 2.855015 72 1 0 4.297986 0.235527 2.675506 73 1 0 3.710672 1.434850 3.834537 74 1 0 2.559293 0.483987 2.892338 75 6 0 1.047145-3.080443 1.434798 76 1 0 0.922576-2.034769 1.712368 77 1 0 0.084866-3.587148 1.545234 78 1 0 1.778813-3.555116 2.104918 79 6 0 1.537675-4.580587-0.366815 80 1 0 2.234058-5.155383 0.260846 81 1 0 0.539846-5.019369-0.287455 82 1 0 1.868590-4.639157-1.402884 12d-monomer E tot = -994.2013993 a.u. (0) 1 6 0 3.459712 0.932866 0.322394 2 6 0 3.774799 2.248102 0.633938 3 6 0 2.800518 3.240266 0.542787 4 6 0 1.513833 2.902320 0.160594 5 6 0 1.192326 1.577117-0.145603 6 6 0 2.170352 0.579323-0.087498 7 6 0-0.192220 1.193320-0.503470 8 6 0 1.781717-0.869034-0.351201 9 6 0 0.476156-0.921375-1.128052 10 7 0-0.421465-0.004399-1.156836 11 6 0 2.912544-1.697580-1.043661 12 6 0 3.135547-2.941529-0.168635 13 6 0 2.804428-2.446596 1.240499 14 6 0 1.543266-1.610205 1.018748 15 7 0 0.215009-2.072871-1.812647 16 7 0-1.140113 1.997942-0.177804 17 7 0-2.437894 1.610690-0.483982 18 6 0-3.345178 2.726999-0.215312 19 6 0-2.822819-1.445769 1.637472 20 6 0-2.313157-0.247851 1.149808 21 6 0-2.904394 0.369307 0.044730 22 6 0-4.017376-0.227721-0.549286 23 6 0-4.529352-1.418541-0.049603 24 6 0-3.932921-2.039103 1.044563 S47
25 1 0 4.232573 0.178980 0.410929 26 1 0 4.781849 2.499183 0.945579 27 1 0 3.045858 4.269470 0.776738 28 1 0 0.729900 3.646726 0.099989 29 1 0 2.666689-1.933224-2.079050 30 1 0 3.826264-1.106627-1.079478 31 1 0 4.145138-3.343920-0.265375 32 1 0 2.441601-3.745827-0.440996 33 1 0 2.651397-3.252605 1.960056 34 1 0 3.615686-1.815381 1.615845 35 1 0 1.337813-0.896389 1.817312 36 1 0 0.673747-2.270239 0.931249 37 1 0 0.744641-2.906187-1.619337 38 1 0-0.743647-2.192083-2.105107 39 1 0-3.012498 3.591005-0.788350 40 1 0-3.357396 2.982708 0.851891 41 1 0-4.351102 2.454773-0.531104 42 1 0-2.352561-1.912437 2.496078 43 1 0-1.452171 0.210130 1.622319 44 1 0-4.459916 0.238758-1.421903 45 1 0-5.391236-1.870638-0.526978 46 1 0-4.328068-2.971587 1.429307 12d-dimer E tot = -1988.4553331 a.u. (0) 1 6 0 1.829378-2.573984-0.286857 2 7 0 1.604049 0.945177-0.101749 3 1 0 2.162044 1.774471 0.025404 4 1 0 0.584953 1.060062-0.046661 5 7 0 1.347675-1.285700-0.294706 6 7 0 1.085722-3.597733-0.546287 7 6 0 2.154649-0.267055-0.146671 8 7 0-0.216667-3.262401-0.969832 9 6 0 3.673930-0.335584-0.103798 10 6 0 4.138991-1.763112 0.105557 11 6 0 5.491765-2.021248 0.355288 12 1 0 6.194095-1.195200 0.403933 13 6 0 5.947280-3.315523 0.541249 14 1 0 6.997858-3.495094 0.737602 15 6 0 5.052808-4.385434 0.474687 16 1 0 5.405115-5.399473 0.620369 17 6 0 3.254982-2.837215 0.026111 18 6 0 3.716840-4.146712 0.210606 19 1 0 3.004678-4.958245 0.132085 20 6 0-0.312523-2.777033-2.336326 21 1 0-0.407764-3.599256-3.057224 22 1 0 0.580875-2.200038-2.559832 23 1 0-1.171099-2.107475-2.433418 24 6 0-1.240880-4.032146-0.449826 25 6 0-1.098778-4.625786 0.819878 S48
26 1 0-0.152670-4.529652 1.335476 27 6 0-2.154355-5.313620 1.393926 28 1 0-2.019423-5.760999 2.372463 29 6 0-3.380426-5.435425 0.738565 30 1 0-4.199790-5.975612 1.195764 31 6 0-3.524622-4.857386-0.515480 32 1 0-4.461131-4.957203-1.053334 33 6 0-2.476662-4.159607-1.112366 34 1 0-2.615846-3.744087-2.102309 35 6 0 4.210204 0.240507-1.465912 36 1 0 5.090480-0.339006-1.754736 37 1 0 3.471050 0.141863-2.263092 38 6 0 4.622107 1.686356-1.174471 39 1 0 5.330507 2.067943-1.912105 40 1 0 3.760052 2.362021-1.183805 41 6 0 5.217686 1.591700 0.231555 42 1 0 5.299926 2.560101 0.726988 43 1 0 6.222840 1.161488 0.171303 44 6 0 4.274108 0.633116 0.977178 45 1 0 3.478817 1.197893 1.466783 46 1 0 4.779135 0.069060 1.760813 47 6 0-1.829413 2.574030 0.286890 48 7 0-1.604034-0.945120 0.101780 49 1 0-2.162022-1.774430-0.025303 50 1 0-0.584934-1.059998 0.046810 51 7 0-1.347682 1.285757 0.294762 52 7 0-1.085771 3.597780 0.546341 53 6 0-2.154641 0.267104 0.146719 54 7 0 0.216622 3.262390 0.969833 55 6 0-3.673919 0.335606 0.103852 56 6 0-4.138996 1.763116-0.105606 57 6 0-5.491762 2.021230-0.355404 58 1 0-6.194088 1.195178-0.404030 59 6 0-5.947278 3.315493-0.541457 60 1 0-6.997849 3.495042-0.737862 61 6 0-5.052818 4.385414-0.474925 62 1 0-5.405127 5.399441-0.620685 63 6 0-3.255001 2.837235-0.026175 64 6 0-3.716859 4.146717-0.210772 65 1 0-3.004706 4.958260-0.132266 66 6 0 0.312464 2.777083 2.336350 67 1 0 0.407590 3.599338 3.057225 68 1 0-0.580892 2.200008 2.559831 69 1 0 1.171100 2.107614 2.433504 70 6 0 1.240838 4.032139 0.449808 71 6 0 1.098717 4.625704-0.819928 72 1 0 0.152603 4.529528-1.335506 73 6 0 2.154280 5.313513-1.394028 74 1 0 2.019339 5.760834-2.372589 75 6 0 3.380356 5.435359-0.738680 76 1 0 4.199716 5.975515-1.195922 S49
77 6 0 3.524566 4.857397 0.515397 78 1 0 4.461088 4.957228 1.053224 79 6 0 2.476611 4.159650 1.112336 80 1 0 2.615811 3.744181 2.102297 81 6 0-4.210144-0.240389 1.466028 82 1 0-5.090490 0.339054 1.754781 83 1 0-3.471007-0.141574 2.263203 84 6 0-4.621864-1.686313 1.174718 85 1 0-5.330164-2.067956 1.912418 86 1 0-3.759698-2.361843 1.184040 87 6 0-5.217533-1.591827-0.231282 88 1 0-5.299700-2.560273-0.726638 89 1 0-6.222730-1.161714-0.171005 90 6 0-4.274082-0.633207-0.977017 91 1 0-3.478775-1.197979-1.466603 92 1 0-4.779174-0.069254-1.760684 13-monomer E tot = -688.4635049 a.u. (0) 1 7 0-0.211382 2.226440-0.137250 2 7 0-2.392313 2.416232 0.460658 3 1 0-2.175084 3.385678 0.637695 4 1 0-3.169795 2.016165 0.956866 5 8 0 1.851064 1.997407-1.022650 6 6 0-1.336175 1.639745 0.099789 7 6 0 0.894403 1.466364-0.511649 8 6 0 0.937488-0.022444-0.123938 9 6 0-0.441659-0.636409-0.111036 10 6 0-0.621926-2.020435-0.136484 11 1 0 0.245143-2.670852-0.173518 12 6 0-1.894025-2.574282-0.120801 13 1 0-2.012878-3.651082-0.148779 14 6 0-3.017412-1.750668-0.085882 15 1 0-4.011906-2.178910-0.101479 16 6 0-2.853008-0.375979-0.033795 17 1 0-3.729233 0.262106-0.033592 18 6 0-1.570517 0.181522-0.021735 19 6 0 1.561412-0.073531 1.320779 20 1 0 1.353635 0.835247 1.889260 21 1 0 1.117473-0.915753 1.860107 22 6 0 3.047110-0.338670 1.082427 23 1 0 3.538690 0.575942 0.739566 24 1 0 3.556937-0.690642 1.981187 25 6 0 3.016599-1.365988-0.049576 26 1 0 2.695529-2.336059 0.347240 27 1 0 3.984058-1.508691-0.533422 28 6 0 1.962587-0.792361-1.008801 29 1 0 1.480228-1.551362-1.625030 30 1 0 2.435297-0.070925-1.674557 13-dimer E tot = -1376.9687809 a.u. (0) S50
1 6 0 4.203375-1.827935-1.258102 2 6 0 3.665089-0.911291-0.111504 3 6 0 4.049638-1.683923 1.205108 4 6 0 4.289884-3.126864 0.762313 5 6 0 5.007721-2.944530-0.575658 6 6 0 4.276271 0.473308-0.108607 7 6 0 3.518826 1.614334 0.148896 8 6 0 2.053604 1.526082 0.365276 9 7 0 1.491440 0.251259 0.165709 10 6 0 2.144969-0.895917-0.138239 11 6 0 4.126190 2.873787 0.195170 12 6 0 5.486936 3.001588-0.013312 13 6 0 6.255084 1.864349-0.268140 14 6 0 5.653744 0.617528-0.311502 15 7 0 1.374897 2.545734 0.683325 16 8 0 1.521329-1.932192-0.355930 17 8 0-1.652440 1.935660 0.768417 18 6 0-2.206414 0.915053 0.403917 19 7 0-1.461058-0.222823 0.186845 20 6 0-2.046066-1.377137-0.014230 21 6 0-3.513824-1.572826 0.064716 22 6 0-4.316467-0.430099 0.086989 23 6 0-3.694630 0.943462 0.044291 24 6 0-4.448873 2.002980 0.904865 25 6 0-5.044569 3.016778-0.083684 26 6 0-4.036894 3.011289-1.233560 27 6 0-3.763419 1.519679-1.420827 28 6 0-4.096010-2.844067 0.120993 29 6 0-5.472638-2.985082 0.155170 30 6 0-6.279275-1.848545 0.130174 31 6 0-5.704290-0.587586 0.099489 32 7 0-1.269051-2.425347-0.287724 33 1 0-0.253739-2.282783-0.337466 34 1 0-1.659806-3.316630-0.533254 35 1 0-6.339176 0.291737 0.088963 36 1 0-7.358108-1.949288 0.146330 37 1 0-5.916384-3.971608 0.204516 38 1 0-3.480635-3.735016 0.164444 39 1 0-2.858186 1.298510-1.990199 40 1 0-4.605997 1.049869-1.936575 41 1 0-3.120938 3.522678-0.926922 42 1 0-4.409959 3.481602-2.145211 43 1 0-6.019699 2.676384-0.450627 44 1 0-5.184350 4.000549 0.366896 45 1 0-5.193304 1.541904 1.554424 46 1 0-3.716377 2.505455 1.535865 47 1 0 0.464470 0.166885 0.214893 48 1 0 0.378573 2.337024 0.787346 49 1 0 6.259578-0.262041-0.503680 50 1 0 7.322722 1.953524-0.432319 S51
51 1 0 5.953436 3.978646 0.022351 52 1 0 3.496901 3.731511 0.397674 53 1 0 3.286431-1.575769 1.978797 54 1 0 4.977142-1.253539 1.591893 55 1 0 3.333602-3.631176 0.604721 56 1 0 4.868773-3.694686 1.493256 57 1 0 6.039612-2.623024-0.396414 58 1 0 5.044220-3.854611-1.176775 59 1 0 4.785632-1.255271-1.979951 60 1 0 3.353085-2.266822-1.779954 b) TD-CAM-B3LYP/6-311+G(d,p) Geometry Optimizations 10a Monomer: E(RCAM-B3LYP) = -857.778286189 au 1 6 0 4.463994 0.101692 0.078664 2 6 0 4.316797 1.460171 0.024991 3 6 0 3.033672 2.033725-0.056494 4 6 0 1.910069 1.242345-0.082361 5 6 0 2.042523-0.168610-0.010522 6 6 0 3.332368-0.748874 0.063550 7 6 0 0.894486-0.996023-0.005023 8 6 0-0.442309-0.348805-0.045229 9 7 0-0.531453 1.022649-0.168065 10 6 0 0.534108 1.765897-0.195533 11 6 0 3.445819-2.156976 0.124897 12 6 0 2.324430-2.942967 0.118994 13 6 0 1.045959-2.360828 0.058226 14 7 0 0.356289 3.094588-0.327941 15 7 0-1.479962-1.101233 0.009778 16 6 0-2.777915-0.570481 0.037415 17 6 0-3.240994 0.200619 1.107005 18 6 0-4.559576 0.628859 1.146125 19 6 0-5.439709 0.304010 0.119613 20 6 0-4.986047-0.466726-0.943607 21 6 0-3.671403-0.911386-0.979564 22 1 0-0.584245 3.429633-0.464990 23 1 0 1.114231 3.732084-0.493139 24 1 0-6.468358 0.642159 0.152308 25 1 0-4.902294 1.223367 1.985484 26 1 0-2.558513 0.456332 1.908054 27 1 0-3.320715-1.527525-1.799143 28 1 0-5.661972-0.733146-1.748166 29 1 0 2.963667 3.113239-0.091361 30 1 0 5.185541 2.105767 0.043688 31 1 0 0.160958-2.983029 0.063134 32 1 0 2.415917-4.021150 0.165394 33 1 0 4.432686-2.602092 0.177721 S52
34 1 0 5.451342-0.341528 0.137748 10a-Dimer: E(RCAM-B3LYP) = -1715.57309908 au 1 7 0-1.143289 1.359177 0.445718 2 6 0-2.127206 0.465282 0.319073 3 7 0-1.806118-0.794864 0.150224 4 6 0-2.783038-1.756979-0.018450 5 7 0-2.530832-3.014708-0.047384 6 1 0-0.166118 1.097568 0.286096 7 1 0-1.339593 2.346530 0.424027 8 6 0 1.190286-4.780946 0.775556 9 6 0 0.535212-4.046331 1.758602 10 6 0-0.676431-3.428615 1.488046 11 6 0-1.262665-3.538135 0.222839 12 6 0-0.611129-4.295036-0.754234 13 6 0 0.608945-4.900686-0.482079 14 7 0 1.111984-1.335030-0.522024 15 6 0 2.104565-0.453645-0.372331 16 7 0 1.797130 0.801711-0.151003 17 6 0 2.786212 1.745841 0.048684 18 7 0 2.550001 3.004552 0.123213 19 1 0 0.140787-1.074981-0.325943 20 1 0 1.302641-2.323854-0.526676 21 6 0-1.142059 4.857258-0.635528 22 6 0-0.491005 4.159652-1.648051 23 6 0 0.710095 3.512782-1.399208 24 6 0 1.289622 3.555477-0.126818 25 6 0 0.642100 4.274837 0.880745 26 6 0-0.567307 4.909865 0.629836 27 6 0-3.524306 0.949146 0.371189 28 6 0-4.197529-1.340404-0.201417 29 6 0-4.534748 0.010477 0.043658 30 6 0-3.873183 2.244028 0.673040 31 6 0-5.219369 2.654585 0.633706 32 6 0-6.202273 1.771573 0.280623 33 6 0-5.886877 0.425890-0.024580 34 6 0-5.185167-2.232050-0.545403 35 6 0-6.525233-1.818235-0.648738 36 6 0-6.873846-0.520314-0.385313 37 6 0 3.496406-0.947313-0.460767 38 6 0 4.196410 1.306268 0.211183 39 6 0 4.518516-0.035237-0.096964 40 6 0 3.830107-2.229256-0.827812 41 6 0 5.172351-2.654371-0.817893 42 6 0 5.866670-0.466851-0.057217 43 6 0 5.194807 2.170994 0.590924 44 6 0 6.531004 1.739049 0.667797 45 6 0 6.865115 0.451632 0.341518 S53
46 6 0 6.166378-1.799418-0.428585 47 1 0 2.136274-5.262569 0.990728 48 1 0 0.973764-3.950817 2.745185 49 1 0-1.182986-2.857632 2.256361 50 1 0-1.072969-4.400846-1.728624 51 1 0 1.101568-5.479137-1.255323 52 1 0-2.079063 5.363113-0.833951 53 1 0-0.924386 4.116356-2.640557 54 1 0 1.213802 2.970905-2.190197 55 1 0 1.098523 4.328278 1.861885 56 1 0-1.057405 5.457811 1.426497 57 1 0-3.126561 2.976909 0.949916 58 1 0-5.467527 3.679552 0.878484 59 1 0-7.237485 2.089950 0.237385 60 1 0-4.915770-3.263756-0.727196 61 1 0-7.283956-2.538930-0.927876 62 1 0-7.908097-0.202131-0.447808 63 1 0 3.074193-2.940119-1.135364 64 1 0 5.408573-3.668527-1.114122 65 1 0 4.937566 3.196232 0.820731 66 1 0 7.298532 2.438265 0.976012 67 1 0 7.896505 0.120948 0.382388 68 1 0 7.198487-2.129879-0.407053 10b-Monomer: E(RCAM-B3LYP) = -897.5771945 au 1 7 0-0.745654 3.108305-0.407161 2 1 0-1.501587 3.722728-0.656715 3 1 0 0.190014 3.419263-0.621330 4 6 0-0.931531 1.773490-0.247984 5 7 0 0.137109 1.022204-0.226330 6 6 0 0.045665-0.348091-0.080232 7 7 0 1.086951-1.117755-0.036544 8 6 0 2.401328-0.636609 0.000497 9 6 0 2.849135 0.361132 0.884745 10 1 0 2.138789 0.848010 1.540214 11 6 0 4.193618 0.717408 0.932035 12 1 0 4.509355 1.486743 1.630720 13 6 0 5.144974 0.114131 0.099641 14 6 0 4.695965-0.880046-0.777823 15 1 0 5.405448-1.371990-1.436443 16 6 0 3.358257-1.263173-0.815348 17 1 0 3.033687-2.049227-1.488432 18 6 0 6.604853 0.492290 0.176363 19 1 0 7.132799-0.112981 0.922097 20 1 0 6.730815 1.539794 0.461298 21 1 0 7.107311 0.338012-0.781603 22 6 0-1.293699-0.990246-0.014530 23 6 0-1.456298-2.363719 0.064934 24 1 0-0.575511-2.992656 0.058651 25 6 0-2.738162-2.937848 0.155831 S54
26 1 0-2.835057-4.015901 0.212757 27 6 0-3.862880-2.141894 0.178833 28 1 0-4.850560-2.583037 0.256415 29 6 0-3.743771-0.732103 0.103241 30 6 0-4.872541 0.127575 0.136852 31 1 0-5.861615-0.309115 0.221917 32 6 0-4.718697 1.492953 0.069493 33 1 0-5.584980 2.142525 0.104373 34 6 0-3.433513 2.061447-0.045314 35 1 0-3.356740 3.141140-0.085820 36 6 0-2.305599 1.259393-0.091817 37 6 0-2.442272-0.154854-0.004059 10b-Dimer: E(RCAM-B3LYP) = =-1794.1770503 au 1 7 0-1.292308 1.155401 0.568657 2 1 0-1.623615 2.105865 0.603348 3 1 0-0.294610 1.044337 0.363557 4 6 0-2.147086 0.143619 0.395005 5 7 0-1.661160-1.047279 0.142017 6 6 0-2.501369-2.122768-0.076229 7 7 0-2.082889-3.330860-0.181142 8 6 0-0.749429-3.690680 0.050652 9 6 0-0.160699-3.571099 1.313786 10 1 0-0.723926-3.113797 2.118094 11 6 0 1.125315-4.032941 1.540648 12 1 0 1.557302-3.927478 2.530532 13 6 0 1.878277-4.624981 0.524757 14 6 0 1.285045-4.743149-0.730090 15 1 0 1.839452-5.203478-1.541374 16 6 0-0.011224-4.297810-0.964165 17 1 0-0.460223-4.414138-1.943515 18 6 0 3.266182-5.144828 0.791391 19 1 0 3.234407-6.067119 1.378101 20 1 0 3.860697-4.422297 1.354611 21 1 0 3.791738-5.364527-0.139164 22 6 0-3.962073-1.891415-0.223009 23 6 0-4.825077-2.885506-0.617366 24 1 0-4.420283-3.856485-0.869291 25 6 0-6.210643-2.653264-0.681025 26 1 0-6.869208-3.451517-1.000608 27 6 0-6.727993-1.435207-0.328475 28 1 0-7.797033-1.259161-0.359411 29 6 0-5.872606-0.387729 0.084794 30 6 0-6.362046 0.880424 0.480009 31 1 0-7.431316 1.057604 0.466050 32 6 0-5.501826 1.864864 0.881663 33 1 0-5.882599 2.828711 1.194917 S55
34 6 0-4.111851 1.640396 0.882350 35 1 0-3.466390 2.448755 1.201122 36 6 0-3.596045 0.427182 0.493281 37 6 0-4.475475-0.617807 0.113581 38 7 0 1.292288-1.155394-0.568707 39 1 0 1.623593-2.105858-0.603410 40 1 0 0.294591-1.044333-0.363591 41 6 0 2.147070-0.143618-0.395038 42 7 0 1.661151 1.047278-0.142024 43 6 0 2.501367 2.122757 0.076244 44 7 0 2.082897 3.330850 0.181177 45 6 0 0.749443 3.690688-0.050620 46 6 0 0.160717 3.571130-1.313758 47 1 0 0.723944 3.113831-2.118069 48 6 0-1.125290 4.032989-1.540621 49 1 0-1.557274 3.927544-2.530508 50 6 0-1.878250 4.625026-0.524726 51 6 0-1.285023 4.743172 0.730125 52 1 0-1.839430 5.203496 1.541412 53 6 0 0.011239 4.297814 0.964201 54 1 0 0.460234 4.414125 1.943555 55 6 0-3.266146 5.144896-0.791362 56 1 0-3.234352 6.067225-1.378012 57 1 0-3.860650 4.422403-1.354642 58 1 0-3.791724 5.364540 0.139194 59 6 0 3.962069 1.891389 0.223027 60 6 0 4.825078 2.885465 0.617412 61 1 0 4.420290 3.856439 0.869362 62 6 0 6.210643 2.653211 0.681069 63 1 0 6.869212 3.451451 1.000675 64 6 0 6.727986 1.435160 0.328487 65 1 0 7.797025 1.259107 0.359419 66 6 0 5.872593 0.387699-0.084813 67 6 0 6.362025-0.880445-0.480063 68 1 0 7.431294-1.057632-0.466108 69 6 0 5.501800-1.864869-0.881746 70 1 0 5.882567-2.828709-1.195027 71 6 0 4.111825-1.640392-0.882428 72 1 0 3.466360-2.448738-1.201222 73 6 0 3.596027-0.427186-0.493324 74 6 0 4.475464 0.617787-0.113596 10c (Monomer): E(RCAM-B3LYP) = -873.834793473 au 1 6 0 0.865324 0.955824 0.000013 2 6 0 0.949233 2.327142 0.000042 3 1 0 0.034164 2.903192 0.000062 4 6 0 2.198784 2.971397 0.000047 5 1 0 2.239727 4.053464 0.000070 S56
6 6 0 3.353884 2.237744 0.000022 7 1 0 4.319453 2.730397 0.000025 8 6 0 4.487426 0.038276-0.000035 9 1 0 5.448662 0.539161-0.000030 10 6 0 4.415535-1.328560-0.000064 11 1 0 5.320843-1.922643-0.000083 12 6 0 3.165824-1.971909-0.000069 13 1 0 3.104680-3.051838-0.000092 14 6 0 2.001350-1.243685-0.000044 15 6 0 2.049559 0.173204-0.000013 16 6 0 3.310412 0.823144-0.000009 17 7 0 0.603551-3.195513-0.000080 18 1 0-0.365358-3.508215-0.000080 19 6 0 0.688794-1.922786-0.000050 20 7 0-0.425598-1.092146-0.000022 21 1 0-1.364414-1.507618-0.000023 22 6 0-0.446051 0.276832 0.000009 23 7 0-1.522136 0.992378 0.000034 24 6 0-2.813322 0.484116 0.000034 25 7 0-3.070584-0.832428 0.000008 26 6 0-4.340666-1.245961 0.000010 27 1 0-4.490068-2.320634-0.000011 28 6 0-5.420324-0.385314 0.000039 29 1 0-6.430186-0.773040 0.000040 30 6 0-5.163018 0.984042 0.000066 31 1 0-5.978536 1.697300 0.000089 32 6 0-3.857240 1.422999 0.000064 33 1 0-3.608635 2.475397 0.000084 12d-Monomer: E(RCAM-B3LYP) = -994.075355424 au 1 6 0 3.386657 1.173035 0.484124 2 6 0 3.535707 2.505598 0.825220 3 6 0 2.455229 3.375990 0.716184 4 6 0 1.234907 2.893400 0.287058 5 6 0 1.076943 1.545463-0.047782 6 6 0 2.163037 0.673730 0.029648 7 6 0-0.241555 1.021409-0.478769 8 6 0 1.998073-0.800445-0.302999 9 6 0 0.681084-1.029051-1.026974 10 7 0-0.328306-0.221323-1.058046 11 6 0 3.205586-1.369408-1.123726 12 6 0 3.679294-2.633359-0.393387 13 6 0 3.365427-2.341079 1.072789 14 6 0 1.995257-1.662761 1.016824 15 7 0 0.537737-2.212381-1.654286 16 7 0-1.263948 1.782195-0.299856 17 7 0-2.509259 1.307378-0.735253 18 6 0-3.399048 2.452822-0.918701 19 6 0-3.175199-1.318606 1.835221 S57
20 6 0-2.563826-0.259838 1.175608 21 6 0-3.085121 0.221809-0.025856 22 6 0-4.231434-0.388569-0.545693 23 6 0-4.839680-1.439384 0.121752 24 6 0-4.316505-1.915837 1.318992 25 1 0 4.241210 0.515833 0.576933 26 1 0 4.496337 2.867285 1.172075 27 1 0 2.567902 4.423096 0.970001 28 1 0 0.377394 3.547221 0.206814 29 1 0 2.943566-1.545533-2.166620 30 1 0 4.008000-0.634852-1.135220 31 1 0 4.734384-2.841932-0.576577 32 1 0 3.120721-3.516699-0.721021 33 1 0 3.356377-3.235344 1.698068 34 1 0 4.113777-1.660806 1.488469 35 1 0 1.779104-1.045581 1.888278 36 1 0 1.214025-2.423304 0.953573 37 1 0 1.251959-2.918756-1.652899 38 1 0-0.354450-2.429137-2.069380 39 1 0-2.946569 3.141495-1.630388 40 1 0-3.572691 2.982751 0.026945 41 1 0-4.353530 2.121183-1.320378 42 1 0-2.752299-1.673676 2.768266 43 1 0-1.679022 0.195438 1.598247 44 1 0-4.635702-0.049582-1.491325 45 1 0-5.723971-1.898127-0.305619 46 1 0-4.789079-2.741584 1.836666 12d-Dimer: E(RCAM-B3LYP) = -1988.17469109 au 1 6 0 2.830890-1.485215-0.191334 2 7 0 1.028735 1.547334-0.117031 3 1 0 1.148581 2.542890-0.055037 4 1 0 0.066023 1.197650-0.040815 5 7 0 1.811785-0.564128-0.210343 6 7 0 2.668692-2.731572-0.476552 7 6 0 2.070312 0.716770-0.151642 8 7 0 1.379216-3.095229-0.924555 9 6 0 3.466467 1.327510-0.222295 10 6 0 4.509537 0.295007 0.166544 11 6 0 5.818583 0.685749 0.460388 12 1 0 6.091732 1.733173 0.425651 13 6 0 6.783488-0.246282 0.796044 14 1 0 7.790591 0.080947 1.025421 15 6 0 6.458460-1.599877 0.840781 16 1 0 7.208230-2.333471 1.111160 17 6 0 4.199908-1.061377 0.184094 18 6 0 5.175378-2.001952 0.528292 19 1 0 4.904181-3.048738 0.535901 20 6 0 1.111027-2.693363-2.298853 S58
21 1 0 1.616413-3.345169-3.022912 22 1 0 1.452504-1.671284-2.433524 23 1 0 0.039408-2.708130-2.494103 24 6 0 0.988306-4.372168-0.520876 25 6 0 1.459433-4.897907 0.692827 26 1 0 2.161801-4.320077 1.276541 27 6 0 1.030834-6.136110 1.139653 28 1 0 1.412701-6.517624 2.079979 29 6 0 0.119369-6.887572 0.404447 30 1 0-0.214591-7.854164 0.760676 31 6 0-0.349942-6.374576-0.795860 32 1 0-1.053709-6.944961-1.391468 33 6 0 0.077634-5.137965-1.263714 34 1 0-0.297659-4.782750-2.212862 35 6 0 3.695491 1.808703-1.704890 36 1 0 4.733520 1.603968-1.972764 37 1 0 3.064765 1.267826-2.411664 38 6 0 3.456541 3.317231-1.694998 39 1 0 3.931726 3.813236-2.543001 40 1 0 2.387568 3.542145-1.749565 41 6 0 4.030370 3.751470-0.347107 42 1 0 3.684621 4.735751-0.027955 43 1 0 5.121483 3.794418-0.412648 44 6 0 3.599124 2.640783 0.622351 45 1 0 2.651934 2.897682 1.094355 46 1 0 4.302533 2.506310 1.441662 47 6 0-2.830891 1.485252 0.191477 48 7 0-1.028788-1.547336 0.117328 49 1 0-1.148638-2.542886 0.055233 50 1 0-0.066063-1.197664 0.041230 51 7 0-1.811814 0.564135 0.210593 52 7 0-2.668690 2.731591 0.476773 53 6 0-2.070358-0.716751 0.151761 54 7 0-1.379250 3.095184 0.924941 55 6 0-3.466536-1.327478 0.222057 56 6 0-4.509523-0.294902-0.166807 57 6 0-5.818530-0.685591-0.460901 58 1 0-6.091699-1.733015-0.426330 59 6 0-6.783367 0.246492-0.796604 60 1 0-7.790439-0.080696-1.026174 61 6 0-6.458310 1.600087-0.841142 62 1 0-7.208026 2.333723-1.111557 63 6 0-4.199867 1.061477-0.184172 64 6 0-5.175268 2.002106-0.528420 65 1 0-4.904048 3.048887-0.535888 66 6 0-1.111253 2.693301 2.299271 67 1 0-1.616701 3.345127 3.023269 68 1 0-1.452795 1.671236 2.433898 69 1 0-0.039658 2.708021 2.494659 70 6 0-0.988217 4.372096 0.521308 71 6 0-1.459207 4.897889-0.692426 S59
72 1 0-2.161570 4.320119-1.276203 73 6 0-1.030473 6.136064-1.139203 74 1 0-1.412239 6.517622-2.079553 75 6 0-0.119000 6.887442-0.403922 76 1 0 0.215068 7.854010-0.760113 77 6 0 0.350180 6.374389 0.796413 78 1 0 1.053953 6.944706 1.392080 79 6 0-0.077537 5.137811 1.264223 80 1 0 0.297654 4.782553 2.213395 81 6 0-3.695854-1.808945 1.704519 82 1 0-4.733899-1.604140 1.972274 83 1 0-3.065172-1.268290 2.411501 84 6 0-3.457084-3.317503 1.694363 85 1 0-3.932491-3.813625 2.542174 86 1 0-2.388148-3.542560 1.749087 87 6 0-4.030700-3.751396 0.346271 88 1 0-3.685036-4.735668 0.027001 89 1 0-5.121833-3.794182 0.411571 90 6 0-3.599058-2.640590-0.622866 91 1 0-2.651739-2.897505-1.094602 92 1 0-4.302195-2.505905-1.442376 S60
c) Calculated Excitations (only the 10 longest wavelength excitations are shown) 10a Monomer (solid) and Dimer (dashed) 80000 Calculated extinction 60000 40000 20000 0 200 250 300 350 400 450 500 Wavelength (nm) 10a-Monomer Excitation energies and oscillator strengths: Excited State 1: Singlet-A 3.4082 ev 363.78 nm f=0.4271 71 -> 72 0.68033 This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = -857.653037016 Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A 3.8564 ev 321.50 nm f=0.1206 66 -> 72-0.12268 70 -> 72 0.66164 Excited State 3: Singlet-A 4.2123 ev 294.34 nm f=0.0087 67 -> 72 0.35180 68 -> 72 0.43602 69 -> 72-0.30500 70 -> 73-0.16429 71 -> 73-0.18876 S61
Excited State 4: Singlet-A 4.4293 ev 279.92 nm f=0.0590 66 -> 72 0.47193 67 -> 72-0.31623 68 -> 72 0.29762 70 -> 72 0.10189 70 -> 73 0.10331 71 -> 73 0.12465 Excited State 5: Singlet-A 4.4834 ev 276.54 nm f=0.0752 66 -> 72 0.37148 67 -> 72 0.32317 68 -> 72-0.14844 69 -> 72 0.36483 70 -> 73-0.15740 71 -> 73-0.15463 Excited State 6: Singlet-A 4.9973 ev 248.10 nm f=0.0115 66 -> 72-0.18687 68 -> 72 0.24826 69 -> 72 0.26375 69 -> 74-0.10291 70 -> 76-0.15143 70 -> 77-0.10138 71 -> 74 0.22800 71 -> 76 0.28501 71 -> 77 0.15051 71 -> 78-0.15336 71 -> 79-0.11750 Excited State 7: Singlet-A 5.1392 ev 241.25 nm f=0.2442 65 -> 72 0.15533 67 -> 72-0.12245 68 -> 72-0.10325 69 -> 72-0.19567 70 -> 74 0.20187 71 -> 73-0.13343 71 -> 74 0.54334 Excited State 8: Singlet-A 5.3112 ev 233.44 nm f=0.0829 65 -> 72 0.12090 66 -> 72-0.15723 68 -> 72 0.30150 69 -> 72 0.37268 70 -> 76 0.14669 71 -> 75-0.10838 71 -> 76-0.31555 71 -> 77-0.10018 71 -> 78 0.10848 Excited State 9: Singlet-A 5.3457 ev 231.93 nm f=0.5744 67 -> 72 0.31311 70 -> 73 0.22298 70 -> 74 0.10179 71 -> 73 0.49731 71 -> 74 0.20222 S62
Excited State 10: Singlet-A 5.4595 ev 227.10 nm f=0.1248 65 -> 72 0.51725 70 -> 74 0.21322 71 -> 72-0.10640 71 -> 74-0.13309 71 -> 76 0.21243 71 -> 77-0.14612 71 -> 79 0.11827 10a-Dimer Excitation energies and oscillator strengths: Excited State 1: Singlet-A 3.4747 ev 356.82 nm f=0.0056 141 -> 144-0.43915 142 -> 143 0.51338 This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = -1715.44540730 Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A 3.5224 ev 351.98 nm f=0.8357 141 -> 143 0.49272 142 -> 144-0.45850 Excited State 3: Singlet-A 3.9683 ev 312.44 nm f=0.1718 139 -> 144-0.44070 140 -> 143 0.49347 Excited State 4: Singlet-A 3.9878 ev 310.91 nm f=0.0000 139 -> 143 0.46605 140 -> 144-0.46486 Excited State 5: Singlet-A 4.2087 ev 294.59 nm f=0.0000 134 -> 143-0.18949 135 -> 144-0.30143 136 -> 143 0.17015 137 -> 143 0.38747 137 -> 144 0.10395 138 -> 143 0.12921 138 -> 144-0.29538 141 -> 146 0.12093 142 -> 145-0.12065 Excited State 6: Singlet-A 4.2192 ev 293.86 nm f=0.0066 134 -> 144 0.22394 135 -> 143 0.33180 136 -> 144-0.17696 137 -> 144-0.32894 138 -> 143 0.29411 138 -> 144-0.10824 141 -> 145-0.13006 142 -> 146 0.12518 S63
Excited State 7: Singlet-A 4.3651 ev 284.04 nm f=0.0001 133 -> 144 0.16672 134 -> 143-0.26341 135 -> 144-0.17037 137 -> 143-0.23917 138 -> 144 0.16867 139 -> 143-0.14380 139 -> 145-0.10869 141 -> 144 0.29646 141 -> 146 0.11833 142 -> 143 0.27512 Excited State 8: Singlet-A 4.4189 ev 280.58 nm f=0.0778 137 -> 144-0.16792 138 -> 143 0.13407 139 -> 144-0.15932 141 -> 143 0.38549 142 -> 144 0.45387 Excited State 9: Singlet-A 4.4506 ev 278.58 nm f=0.2053 133 -> 143-0.19529 134 -> 143 0.10369 134 -> 144 0.25469 135 -> 143 0.17629 137 -> 143 0.15792 137 -> 144 0.25509 138 -> 143-0.25320 139 -> 146 0.11884 140 -> 145-0.12580 141 -> 143 0.14509 141 -> 144 0.13900 141 -> 145-0.13409 142 -> 143 0.14792 142 -> 144 0.12296 142 -> 146 0.14590 Excited State 10: Singlet-A 4.4616 ev 277.89 nm f=0.0213 133 -> 144-0.13182 134 -> 143 0.15115 135 -> 144 0.12936 138 -> 143 0.15053 138 -> 144-0.18630 141 -> 143-0.19960 141 -> 144 0.38120 142 -> 143 0.29642 142 -> 145 0.11263 S64
10b Monomer (solid) and Dimer (dashed) 10b-Monomer Excitation energies and oscillator strengths: Excited State 1: Singlet-A 3.2832 ev 377.63 nm f=0.4695 75 -> 76 0.67844 This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = -896.959326724 Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A 3.8645 ev 320.83 nm f=0.1294 70 -> 76 0.13971 74 -> 76 0.65812 Excited State 3: Singlet-A 4.2121 ev 294.35 nm f=0.0074 71 -> 76-0.35385 72 -> 76 0.49704 73 -> 76-0.16626 74 -> 77 0.18373 75 -> 77 0.18817 Excited State 4: Singlet-A 4.4020 ev 281.66 nm f=0.0386 69 -> 76 0.13078 70 -> 76 0.49079 71 -> 76 0.26219 72 -> 76 0.27211 73 -> 76 0.14725 74 -> 76-0.11956 S65
Excited State 5: Singlet-A 4.4713 ev 277.29 nm f=0.0848 70 -> 76-0.27129 71 -> 76 0.35854 72 -> 76 0.28914 73 -> 76-0.31032 74 -> 77-0.18084 75 -> 77-0.16420 75 -> 78 0.10467 Excited State 6: Singlet-A 4.8764 ev 254.26 nm f=0.0115 70 -> 76 0.20870 72 -> 76-0.13976 73 -> 76-0.25421 73 -> 78 0.12193 73 -> 80-0.10528 74 -> 80-0.12030 75 -> 78 0.18945 75 -> 79 0.12684 75 -> 80 0.32742 75 -> 81 0.17677 75 -> 82-0.22092 75 -> 83-0.12985 Excited State 7: Singlet-A 5.0363 ev 246.18 nm f=0.2758 69 -> 76 0.10502 71 -> 76-0.12284 73 -> 76 0.17639 74 -> 78 0.19100 75 -> 77-0.11835 75 -> 78 0.57117 75 -> 80-0.10554 Excited State 8: Singlet-A 5.2440 ev 236.43 nm f=0.1363 69 -> 76-0.14843 70 -> 76-0.19310 72 -> 76 0.17469 73 -> 76 0.47228 75 -> 77 0.13858 75 -> 79 0.12725 75 -> 80 0.27518 75 -> 82-0.11918 Excited State 9: Singlet-A 5.2580 ev 235.80 nm f=0.3446 69 -> 76-0.21788 71 -> 76 0.27213 74 -> 77 0.18881 75 -> 76 0.10741 75 -> 77 0.45516 75 -> 78 0.19259 75 -> 80-0.15051 Excited State 10: Singlet-A 5.3663 ev 231.04 nm f=0.2271 68 -> 76-0.16164 69 -> 76 0.40763 70 -> 76-0.10231 71 -> 76 0.13098 S66
74 -> 78 0.26475 75 -> 77 0.22071 75 -> 80 0.19571 75 -> 81-0.18835 75 -> 83 0.12577 10b-Dimer Excitation energies and oscillator strengths: Excited State 1: Singlet-A 3.4148 ev 363.08 nm f=0.0000 149 -> 152-0.44744 150 -> 151 0.50633 This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = -1794.05156013 Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A 3.4631 ev 358.01 nm f=0.7969 149 -> 151 0.48531 150 -> 152-0.46907 Excited State 3: Singlet-A 3.9295 ev 315.52 nm f=0.2413 147 -> 152-0.44795 148 -> 151 0.49079 Excited State 4: Singlet-A 3.9493 ev 313.94 nm f=0.0000 147 -> 151-0.46698 148 -> 152 0.46823 Excited State 5: Singlet-A 4.2057 ev 294.80 nm f=0.0000 142 -> 151 0.19933 143 -> 152 0.28480 144 -> 151-0.13027 145 -> 151 0.40951 146 -> 152-0.31742 149 -> 152 0.10748 150 -> 153-0.10896 Excited State 6: Singlet-A 4.2210 ev 293.73 nm f=0.0071 142 -> 152 0.25801 143 -> 151 0.32450 144 -> 152-0.13284 145 -> 152 0.34419 146 -> 151-0.31465 147 -> 154 0.11297 148 -> 153-0.11265 149 -> 153 0.11901 150 -> 154-0.11522 Excited State 7: Singlet-A 4.2674 ev 290.54 nm f=0.0000 142 -> 151-0.13773 143 -> 152-0.10412 S67
147 -> 151 0.12403 149 -> 152 0.47884 150 -> 151 0.43292 Excited State 8: Singlet-A 4.2705 ev 290.33 nm f=0.0078 147 -> 152 0.13689 149 -> 151 0.46436 150 -> 152 0.48699 Excited State 9: Singlet-A 4.4038 ev 281.54 nm f=0.0000 141 -> 152 0.25245 142 -> 151 0.32337 143 -> 152 0.19308 145 -> 151-0.29119 146 -> 152 0.25955 147 -> 153 0.14786 148 -> 154-0.15131 149 -> 152 0.12503 149 -> 154 0.12665 150 -> 151 0.10032 150 -> 153-0.13833 Excited State 10: Singlet-A 4.4411 ev 279.17 nm f=0.2825 141 -> 151 0.25485 142 -> 152 0.28891 143 -> 151 0.15993 145 -> 152-0.30395 146 -> 151 0.32281 147 -> 154 0.15269 148 -> 153-0.15848 149 -> 153 0.13614 150 -> 154-0.14910 S68
10c-Monomer Excitation energies and oscillator strengths: Excited State 1: Singlet-A 3.6217 ev 342.33 nm f=0.7665 71 -> 72 0.68714 This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = -873.701697515 Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A 4.1098 ev 301.68 nm f=0.0887 69 -> 72 0.12300 70 -> 72 0.66066 71 -> 73-0.15101 Excited State 3: Singlet-A 4.3197 ev 287.02 nm f=0.0957 69 -> 72 0.56959 69 -> 73 0.10473 70 -> 72-0.12228 70 -> 75 0.17465 71 -> 75-0.30254 Excited State 4: Singlet-A 4.6067 ev 269.14 nm f=0.0023 63 -> 73 0.11513 67 -> 72-0.21730 68 -> 72 0.60833 68 -> 73-0.14663 Excited State 5: Singlet-A 4.9208 ev 251.96 nm f=0.0710 66 -> 72-0.14537 70 -> 72 0.13855 S69
70 -> 74-0.20978 71 -> 73 0.57623 71 -> 74-0.11976 Excited State 6: Singlet-A 5.0043 ev 247.75 nm f=0.0022 67 -> 72 0.54120 67 -> 73-0.32825 68 -> 72 0.21134 Excited State 7: Singlet-A 5.0449 ev 245.76 nm f=0.1123 65 -> 72-0.16608 70 -> 73-0.27186 70 -> 74 0.14292 70 -> 77-0.10306 71 -> 73 0.20589 71 -> 74 0.52314 Excited State 8: Singlet-A 5.3216 ev 232.99 nm f=0.0007 63 -> 72 0.56511 63 -> 77 0.13724 63 -> 86-0.10239 67 -> 73 0.10693 68 -> 73 0.26723 Excited State 9: Singlet-A 5.4054 ev 229.37 nm f=0.6192 69 -> 72 0.33289 70 -> 74 0.10777 70 -> 75-0.22642 71 -> 75 0.51586 Excited State 10: Singlet-A 5.4710 ev 226.62 nm f=0.1729 64 -> 72 0.21418 70 -> 73 0.44057 70 -> 74 0.28681 71 -> 73 0.14606 71 -> 74 0.17175 71 -> 77-0.25369 S70
12d Monomer (solid) and Dimer (dashed) 12d-Monomer Excitation energies and oscillator strengths: Excited State 1: Singlet-A 3.7031 ev 334.81 nm f=0.2692 85 -> 86 0.67454 This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = -993.939268557 Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A 4.6153 ev 268.64 nm f=0.1035 85 -> 87 0.34538 85 -> 89 0.50689 85 -> 91-0.15660 85 -> 93-0.19409 Excited State 3: Singlet-A 4.9050 ev 252.77 nm f=0.0912 80 -> 86 0.23958 85 -> 87 0.14805 85 -> 88 0.17279 85 -> 91 0.37141 85 -> 92-0.35141 85 -> 94 0.19496 Excited State 4: Singlet-A 4.9312 ev 251.43 nm f=0.0008 79 -> 86 0.10058 81 -> 86 0.12699 81 -> 87 0.10745 82 -> 86-0.29311 S71
83 -> 86 0.22276 83 -> 87-0.13111 83 -> 88 0.12301 84 -> 86-0.12949 85 -> 87 0.32476 85 -> 88-0.26246 85 -> 89-0.15988 Excited State 5: Singlet-A 4.9633 ev 249.80 nm f=0.0110 79 -> 86-0.24111 80 -> 86 0.36120 80 -> 93 0.10388 81 -> 86-0.21562 83 -> 86 0.20565 84 -> 86 0.16657 85 -> 88-0.21074 85 -> 91-0.13873 85 -> 92 0.13152 Excited State 6: Singlet-A 5.2021 ev 238.33 nm f=0.2411 79 -> 86-0.11270 80 -> 86-0.28170 82 -> 86-0.12098 84 -> 86 0.45419 84 -> 89 0.10469 85 -> 87 0.10890 85 -> 88 0.12352 85 -> 91 0.17968 85 -> 92 0.10074 85 -> 93 0.14156 Excited State 7: Singlet-A 5.2130 ev 237.84 nm f=0.0673 79 -> 86 0.10955 81 -> 86-0.13438 82 -> 86 0.10987 84 -> 86-0.12181 85 -> 88-0.29060 85 -> 89 0.27084 85 -> 90 0.18097 85 -> 93 0.38666 85 -> 94 0.12301 85 -> 97-0.10684 Excited State 8: Singlet-A 5.3468 ev 231.89 nm f=0.0171 82 -> 86 0.20596 83 -> 86-0.23868 84 -> 86-0.18884 85 -> 87 0.34256 85 -> 91 0.16571 85 -> 92 0.28981 85 -> 93 0.14231 85 -> 94-0.19592 Excited State 9: Singlet-A 5.4590 ev 227.12 nm f=0.2217 79 -> 86 0.19116 81 -> 86-0.19634 83 -> 86 0.39754 S72
84 -> 86-0.20748 85 -> 87-0.12786 85 -> 88 0.32349 85 -> 92 0.17998 Excited State 10: Singlet-A 5.5630 ev 222.87 nm f=0.0706 79 -> 86-0.13876 80 -> 86 0.22766 81 -> 86 0.32543 82 -> 86-0.24162 83 -> 86-0.11147 83 -> 87-0.11677 85 -> 87-0.14674 85 -> 88 0.11079 85 -> 89 0.22760 85 -> 90 0.14403 85 -> 91 0.13069 85 -> 92 0.15148 85 -> 93 0.15094 12d-Dimer Excitation energies and oscillator strengths: Excited State 1: Singlet-A 3.7130 ev 333.92 nm f=0.0000 159 -> 171 0.10205 169 -> 172 0.45327 170 -> 171 0.49560 This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = -1988.03824023 Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A 3.7481 ev 330.79 nm f=0.5941 159 -> 172 0.10243 169 -> 171 0.46408 170 -> 172 0.48401 Excited State 3: Singlet-A 4.5753 ev 270.98 nm f=0.0412 169 -> 176 0.17111 169 -> 177-0.13011 169 -> 178 0.35957 169 -> 180 0.11176 170 -> 176 0.24840 170 -> 177-0.18780 170 -> 178 0.26595 170 -> 179-0.12713 170 -> 180 0.15678 Excited State 4: Singlet-A 4.5754 ev 270.98 nm f=0.0211 169 -> 176 0.23888 169 -> 177-0.18162 169 -> 178-0.25752 169 -> 179-0.12455 169 -> 180 0.15607 170 -> 176-0.17794 170 -> 177 0.13450 S73
170 -> 178 0.37134 170 -> 180-0.11234 Excited State 5: Singlet-A 4.8857 ev 253.77 nm f=0.0871 169 -> 171 0.45133 170 -> 172-0.41907 170 -> 174 0.16794 170 -> 180-0.12248 170 -> 182-0.14952 Excited State 6: Singlet-A 4.8918 ev 253.46 nm f=0.0000 169 -> 172 0.45754 169 -> 174-0.15716 169 -> 180 0.10104 169 -> 182 0.12412 170 -> 171-0.43260 Excited State 7: Singlet-A 4.9549 ev 250.22 nm f=0.1740 162 -> 171-0.11268 165 -> 172-0.23040 166 -> 171-0.22341 167 -> 174-0.10879 169 -> 171-0.12378 169 -> 173 0.26964 169 -> 175-0.16060 169 -> 188-0.13433 170 -> 172 0.13906 170 -> 174 0.23800 170 -> 177 0.13079 170 -> 179-0.10786 170 -> 186-0.16536 Excited State 8: Singlet-A 4.9606 ev 249.94 nm f=0.0000 162 -> 172-0.10822 165 -> 171-0.23068 166 -> 172-0.19214 166 -> 174-0.12317 169 -> 172 0.13240 169 -> 174 0.22523 169 -> 177 0.13583 169 -> 179-0.11650 169 -> 186-0.15074 170 -> 173 0.31491 170 -> 175-0.16487 170 -> 181-0.10640 170 -> 188-0.12931 Excited State 9: Singlet-A 4.9949 ev 248.22 nm f=0.0000 165 -> 171 0.16124 166 -> 172 0.15079 169 -> 174-0.15406 169 -> 176 0.10150 169 -> 177 0.12989 169 -> 179-0.17963 169 -> 180-0.11903 169 -> 186-0.23507 170 -> 173 0.23774 S74
170 -> 175 0.27547 170 -> 181-0.12305 170 -> 188-0.22174 Excited State 10: Singlet-A 5.0008 ev 247.93 nm f=0.3766 165 -> 172 0.11871 166 -> 171 0.11849 169 -> 173 0.21685 169 -> 175 0.26225 169 -> 181-0.12578 169 -> 188-0.22411 170 -> 174-0.17896 170 -> 176 0.11045 170 177 0.13131 170 -> 179-0.18553 170 -> 180-0.11936 170 -> 186-0.25714 S75
d) Orbitalplots (TD-CAM-B3LYP/6-311+G(d,p) with orbital numbering and energies (ev)) 10a-Monomer HOMO-1 LUMO+1 70 (HOMO-1) -0.28831 71 (HOMO) -0.26552 72 (LUMO) -0.05537 73 (LUMO+1) 0.00865 S76
10a-Dimer HOMO-1 LUMO+1 141 (HOMO-1) -0.26945 142 (HOMO) -0.26781 143 (LUMO) -0.05498 144 (LUMO+1) -0.05246 S77
10b-Monomer HOMO-1 LUMO+1 74 (HOMO-1) -0.28781 75 (HOMO) -0.25811 76 (LUMO) -0.05498 77 (LUMO+1) 0.00907 S78
10b-Dimer HOMO-1 LUMO+1 149 (HOMO-1) -0.26470 150 (HOMO) -0.26305 151 (LUMO) -0.05386 152 (LUMO+1) -0.05194 S79
10c-Monomer HOMO-1 LUMO+1 70 (HOMO-1) -0.29167 71 (HOMO) -0.27347 72 (LUMO) -0.05518 73 (LUMO+1) -0.00049 S80
12d-Monomer HOMO-1 LUMO+1 84 (HOMO-1) -0.29781 85 (HOMO) -0.24392 86 (LUMO) -0.00925 87 (LUMO+1) 0.02222 S81
12d-Dimer HOMO-1 LUMO+1 169 (HOMO-1) -0.24411 170 (HOMO) -0.24181 171 (LUMO) -0.01020 172 (LUMO+1) -0.00950 S82