NH-Type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications

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Supporting Information NH-Type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications Mackenzie Bergagnini, a Kazunobu Fukushi, b Jianlin Han, c Norio Shibata, b Christian Roussel, d Trevor K. Ellis, a José Luis Aceña e and Vadim A. Soloshonok*,e,f a Department of Chemistry and Physics, 100 Campus Drive, Weatherford, OK 73096-3098, United States b Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan c School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China d Chirosciences, ISM2 UMR7313, Aix-Marseille University, France e Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 San Sebastián, Spain. Fax: +34 943-015270; Tel: +34 943-015177; E-mail: vadym.soloshonok@ehu.es f IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain Table of Contents Figure 1. Thermal Ellipsoid Plot of Structure. 2 Figure 2. Packing Diagram... 3 Comments 4 Experimental... 4 Acknowledgements. 5 References... 5 Table 1. Crystal Data.. 6 Table 2. Atom Coordinates... 7 Table 3. Bond Distances and Angles.. 8 Table 4. Anisotropic Displacement Parameters.. 11 Table 5. Hydrogen Atom Parameters... 12 Table 6. Torsion Angles.. 13 NMR spectra 15

2

3

Comment The displacement ellipsoids were drawn at the 50% probability level. Experimental A red prism-shaped crystal of dimensions 0.47 x 0.15 x 0.13 mm was selected for structural analysis. Intensity data for this compound were collected using an instrument with a Bruker APEX ccd area detector (1) with graphite-monochromated Mo Kα radiation (λ = 0.71073 Å). The sample was cooled to 100(2) K. Cell parameters were determined from a non-linear least squares fit of 7600 peaks in the range 2.27 < θ < 28.27. A total of 9916 data were measured in the range 1.98 < θ < 26.00 using ω oscillation frames. The data were corrected for absorption by the semi-empirical method (2) giving minimum and maximum transmission factors of 0.6730 and 0.8903. The data were merged to form a set of 4890 independent data with R(int) = 0.0200 and a coverage of 98.7 %. The triclinic space group P 1 was determined by statistical tests and verified by subsequent refinement. The structure was solved by direct methods and refined by fullmatrix least-squares methods on F 2 (3). Hydrogen atom positions were initially determined by geometry and refined by a riding model. Non-hydrogen atoms were refined with anisotropic displacement parameters. Hydrogen atom displacement parameters were set to 1.2 (1.5 for methyl) times the displacement parameters of the bonded atoms. A total of 331 parameters were refined against 4890 data to give wr(f 2 ) = 0.0813 and S = 1.006 for weights of w = 1/[σ 2 (F 2 ) + (0.0420 P) 2 + 0.9000 P], where P = [F 2 o + 2F 2 c ] / 3. The final R(F) was 0.0321 for the 4458 observed, [F > 4σ(F)], data. The largest shift/s.u. was 0.001 in the final refinement cycle. The final difference map had maxima and minima of 0.392 and -0.230 e/å 3, respectively. 4

Acknowledgment The authors thank the National Science Foundation (grant CHE-0130835) and the University of Oklahoma for funds to purchase of the X-ray instrument and computers. This structure was determined by Hisanori Ueki. References (1) (a) Data Collection: SMART Software Reference Manual (1998). Bruker-AXS, 5465 E. Cheryl Parkway, Madison, WI 53711-5373 USA. (b) Data Reduction: SAINT Software Reference Manual (1998). Bruker-AXS, 5465 E. Cheryl Parkway, Madison, WI 53711-5373 USA. (2) G. M. Sheldrick (2002). SADABS. Program for Empirical Absorption Correction of Area Detector Data. University of Göttingen, Germany. (3) (a) G. M. Sheldrick (2000). SHELXTL Version 6.10 Reference Manual. Bruker-AXS, 5465 E. Cheryl Parkway, Madison, WI 53711-5373 USA. (b) International Tables for Crystallography, Vol C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2, Kluwer: Boston (1995). 5

Table 1. Crystal data and structure refinement for 06087. Empirical formula C 28 H 28 Cl N 3 Ni O 3 Formula weight 548.69 Crystal system Triclinic Space group P 1 Unit cell dimensions a = 9.263(2) Å α= 86.448(7) b = 10.294(2) Å β= 75.238(7) c = 13.643(3) Å γ= 89.471(7) Volume 1255.5(5) Å 3 Z, Z' 2, 1 Density (calculated) 1.451 Mg/m 3 Wavelength 0.71073 Å Temperature 100(2) K F(000) 572 Absorption coefficient 0.915 mm -1 Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.8903 and 0.6730 Theta range for data collection 1.98 to 26.00 Reflections collected 9916 Independent reflections 4890 [R(int) = 0.0200] Data / restraints / parameters 4890 / 0 / 331 wr(f 2 all data) wr2 = 0.0813 R(F obsd data) R1 = 0.0321 Goodness-of-fit on F 2 1.006 Observed data [I > 2σ(I)] 4458 Largest and mean shift / s.u. 0.001and 0.000 Largest diff. peak and hole 0.392 and -0.230 e/å 3 ---------- wr2 = { Σ [w(f 2 o - F 2 c ) 2 ] / Σ [w(f 2 o ) 2 ] } 1/2 R1 = Σ F o - F c / Σ F o 6

Table 2. Atomic coordinates and equivalent isotropic displacement parameters for 06087. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) Ni(1) 0.56214(3) 0.24272(2) 0.612657(17) 0.01300(8) Cl(1) 0.42132(5) 0.72839(5) 0.97526(4) 0.01921(11) O(1) 0.92509(16) 0.36666(16) 0.67183(12) 0.0278(4) O(2) 0.44743(15) 0.13973(13) 0.55160(10) 0.0170(3) O(3) 0.24907(15) 0.00521(13) 0.59338(11) 0.0196(3) N(1) 0.67491(17) 0.34274(16) 0.67261(12) 0.0159(3) N(2) 0.40168(17) 0.23225(15) 0.72605(12) 0.0140(3) N(3) 0.73452(18) 0.24374(16) 0.49762(12) 0.0152(3) C(1) 0.7411(2) 0.34434(19) 0.41029(15) 0.0190(4) C(2) 0.7531(3) 0.4809(2) 0.44548(17) 0.0273(5) C(3) 0.8747(2) 0.3160(2) 0.32155(16) 0.0246(5) C(4) 0.5980(2) 0.3300(2) 0.37652(16) 0.0258(5) C(5) 0.8639(2) 0.2487(2) 0.54287(15) 0.0185(4) C(6) 0.8258(2) 0.3273(2) 0.63658(15) 0.0192(4) C(7) 0.6158(2) 0.42995(19) 0.74632(14) 0.0161(4) C(8) 0.6983(2) 0.5400(2) 0.75767(15) 0.0208(4) C(9) 0.6390(2) 0.6323(2) 0.82523(15) 0.0203(4) C(10) 0.4953(2) 0.61422(18) 0.88689(14) 0.0161(4) C(11) 0.4103(2) 0.50874(18) 0.87892(14) 0.0150(4) C(12) 0.4671(2) 0.41570(18) 0.80752(14) 0.0140(4) C(13) 0.3684(2) 0.30825(18) 0.80047(14) 0.0140(4) C(14) 0.2224(2) 0.29316(17) 0.87907(14) 0.0144(4) C(15) 0.2139(2) 0.24061(19) 0.97688(15) 0.0184(4) C(16) 0.0767(2) 0.2343(2) 1.04830(15) 0.0227(4) C(17) -0.0504(2) 0.2801(2) 1.02286(16) 0.0234(4) C(18) -0.0424(2) 0.3306(2) 0.92512(16) 0.0224(4) C(19) 0.0934(2) 0.33698(19) 0.85305(15) 0.0182(4) C(20) 0.3130(2) 0.11428(18) 0.72536(14) 0.0167(4) C(21) 0.3656(2) 0.00019(19) 0.78750(15) 0.0196(4) C(22) 0.5339(2) -0.01037(18) 0.76791(15) 0.0193(4) C(23) 0.6037(3) 0.02920(19) 0.84022(16) 0.0231(4) C(24) 0.7580(3) 0.0259(2) 0.82321(18) 0.0289(5) C(25) 0.8449(3) -0.0195(2) 0.73360(18) 0.0276(5) C(26) 0.7768(2) -0.0608(2) 0.66181(17) 0.0253(5) C(27) 0.6225(2) -0.05533(19) 0.67795(15) 0.0211(4) C(28) 0.3352(2) 0.08263(18) 0.61454(15) 0.0165(4) 7

Table 3. Bond lengths [Å] and angles [ ] for 06087. Ni(1)-N(1) 1.8384(16) Ni(1)-N(2) 1.8506(16) Ni(1)-O(2) 1.8784(13) Ni(1)-N(3) 1.9324(17) Cl(1)-C(10) 1.745(2) O(1)-C(6) 1.224(2) O(2)-C(28) 1.287(2) O(3)-C(28) 1.230(2) N(1)-C(6) 1.370(2) N(1)-C(7) 1.393(3) N(2)-C(13) 1.293(3) N(2)-C(20) 1.474(2) N(3)-C(5) 1.484(2) N(3)-C(1) 1.519(2) N(3)-H(3N) 0.80(2) C(1)-C(4) 1.521(3) C(1)-C(2) 1.527(3) C(1)-C(3) 1.535(3) C(2)-H(2A) 0.9800 C(2)-H(2B) 0.9800 C(2)-H(2C) 0.9800 C(3)-H(3A) 0.9800 C(3)-H(3B) 0.9800 C(3)-H(3C) 0.9800 C(4)-H(4A) 0.9800 C(4)-H(4B) 0.9800 C(4)-H(4C) 0.9800 C(5)-C(6) 1.519(3) C(5)-H(5A) 0.9900 C(5)-H(5B) 0.9900 C(7)-C(8) 1.410(3) C(7)-C(12) 1.421(3) C(8)-C(9) 1.377(3) C(8)-H(8) 0.9500 C(9)-C(10) 1.388(3) N(1)-Ni(1)-N(2) 93.68(7) N(1)-Ni(1)-O(2) 179.70(7) N(2)-Ni(1)-O(2) 86.35(6) N(1)-Ni(1)-N(3) 86.36(7) N(2)-Ni(1)-N(3) 176.38(7) O(2)-Ni(1)-N(3) 93.59(7) C(28)-O(2)-Ni(1) 114.18(12) C(6)-N(1)-C(7) 121.64(16) C(6)-N(1)-Ni(1) 114.08(13) 8 C(9)-H(9) 0.9500 C(10)-C(11) 1.373(3) C(11)-C(12) 1.410(3) C(11)-H(11) 0.9500 C(12)-C(13) 1.465(3) C(13)-C(14) 1.498(2) C(14)-C(15) 1.392(3) C(14)-C(19) 1.394(3) C(15)-C(16) 1.390(3) C(15)-H(15) 0.9500 C(16)-C(17) 1.381(3) C(16)-H(16) 0.9500 C(17)-C(18) 1.385(3) C(17)-H(17) 0.9500 C(18)-C(19) 1.385(3) C(18)-H(18) 0.9500 C(19)-H(19) 0.9500 C(20)-C(28) 1.528(3) C(20)-C(21) 1.553(3) C(20)-H(20) 1.0000 C(21)-C(22) 1.517(3) C(21)-H(21A) 0.9900 C(21)-H(21B) 0.9900 C(22)-C(23) 1.392(3) C(22)-C(27) 1.394(3) C(23)-C(24) 1.389(3) C(23)-H(23) 0.9500 C(24)-C(25) 1.387(3) C(24)-H(24) 0.9500 C(25)-C(26) 1.381(3) C(25)-H(25) 0.9500 C(26)-C(27) 1.392(3) C(26)-H(26) 0.9500 C(27)-H(27) 0.9500 C(7)-N(1)-Ni(1) 124.27(13) C(13)-N(2)-C(20) 121.53(16) C(13)-N(2)-Ni(1) 128.71(13) C(20)-N(2)-Ni(1) 109.68(12) C(5)-N(3)-C(1) 114.02(15) C(5)-N(3)-Ni(1) 104.40(12) C(1)-N(3)-Ni(1) 118.10(12) C(5)-N(3)-H(3N) 110.4(17) C(1)-N(3)-H(3N) 105.6(17)

Ni(1)-N(3)-H(3N) 103.9(17) N(3)-C(1)-C(4) 107.10(16) N(3)-C(1)-C(2) 109.98(16) C(4)-C(1)-C(2) 110.51(18) N(3)-C(1)-C(3) 109.46(16) C(4)-C(1)-C(3) 108.85(17) C(2)-C(1)-C(3) 110.86(17) C(1)-C(2)-H(2A) 109.5 C(1)-C(2)-H(2B) 109.5 H(2A)-C(2)-H(2B) 109.5 C(1)-C(2)-H(2C) 109.5 H(2A)-C(2)-H(2C) 109.5 H(2B)-C(2)-H(2C) 109.5 C(1)-C(3)-H(3A) 109.5 C(1)-C(3)-H(3B) 109.5 H(3A)-C(3)-H(3B) 109.5 C(1)-C(3)-H(3C) 109.5 H(3A)-C(3)-H(3C) 109.5 H(3B)-C(3)-H(3C) 109.5 C(1)-C(4)-H(4A) 109.5 C(1)-C(4)-H(4B) 109.5 H(4A)-C(4)-H(4B) 109.5 C(1)-C(4)-H(4C) 109.5 H(4A)-C(4)-H(4C) 109.5 H(4B)-C(4)-H(4C) 109.5 N(3)-C(5)-C(6) 110.42(16) N(3)-C(5)-H(5A) 109.6 C(6)-C(5)-H(5A) 109.6 N(3)-C(5)-H(5B) 109.6 C(6)-C(5)-H(5B) 109.6 H(5A)-C(5)-H(5B) 108.1 O(1)-C(6)-N(1) 127.81(19) O(1)-C(6)-C(5) 120.26(18) N(1)-C(6)-C(5) 111.92(16) N(1)-C(7)-C(8) 120.89(17) N(1)-C(7)-C(12) 121.01(17) C(8)-C(7)-C(12) 117.96(18) C(9)-C(8)-C(7) 122.11(19) C(9)-C(8)-H(8) 118.9 C(7)-C(8)-H(8) 118.9 C(8)-C(9)-C(10) 119.02(18) C(8)-C(9)-H(9) 120.5 C(10)-C(9)-H(9) 120.5 C(11)-C(10)-C(9) 121.15(18) C(11)-C(10)-Cl(1) 119.55(15) C(9)-C(10)-Cl(1) 119.30(15) C(10)-C(11)-C(12) 120.64(18) C(10)-C(11)-H(11) 119.7 9 C(12)-C(11)-H(11) 119.7 C(11)-C(12)-C(7) 119.04(17) C(11)-C(12)-C(13) 117.76(17) C(7)-C(12)-C(13) 123.20(17) N(2)-C(13)-C(12) 121.42(17) N(2)-C(13)-C(14) 120.49(16) C(12)-C(13)-C(14) 117.99(16) C(15)-C(14)-C(19) 119.90(18) C(15)-C(14)-C(13) 121.79(17) C(19)-C(14)-C(13) 118.28(17) C(16)-C(15)-C(14) 119.51(18) C(16)-C(15)-H(15) 120.2 C(14)-C(15)-H(15) 120.2 C(17)-C(16)-C(15) 120.45(18) C(17)-C(16)-H(16) 119.8 C(15)-C(16)-H(16) 119.8 C(16)-C(17)-C(18) 120.07(19) C(16)-C(17)-H(17) 120.0 C(18)-C(17)-H(17) 120.0 C(19)-C(18)-C(17) 120.11(19) C(19)-C(18)-H(18) 119.9 C(17)-C(18)-H(18) 119.9 C(18)-C(19)-C(14) 119.94(18) C(18)-C(19)-H(19) 120.0 C(14)-C(19)-H(19) 120.0 N(2)-C(20)-C(28) 107.32(15) N(2)-C(20)-C(21) 109.91(15) C(28)-C(20)-C(21) 111.06(16) N(2)-C(20)-H(20) 109.5 C(28)-C(20)-H(20) 109.5 C(21)-C(20)-H(20) 109.5 C(22)-C(21)-C(20) 114.06(16) C(22)-C(21)-H(21A) 108.7 C(20)-C(21)-H(21A) 108.7 C(22)-C(21)-H(21B) 108.7 C(20)-C(21)-H(21B) 108.7 H(21A)-C(21)-H(21B) 107.6 C(23)-C(22)-C(27) 118.4(2) C(23)-C(22)-C(21) 119.50(19) C(27)-C(22)-C(21) 122.05(18) C(24)-C(23)-C(22) 121.2(2) C(24)-C(23)-H(23) 119.4 C(22)-C(23)-H(23) 119.4 C(25)-C(24)-C(23) 119.9(2) C(25)-C(24)-H(24) 120.1 C(23)-C(24)-H(24) 120.1 C(26)-C(25)-C(24) 119.5(2) C(26)-C(25)-H(25) 120.2

C(24)-C(25)-H(25) 120.2 C(25)-C(26)-C(27) 120.6(2) C(25)-C(26)-H(26) 119.7 C(27)-C(26)-H(26) 119.7 C(26)-C(27)-C(22) 120.3(2) C(26)-C(27)-H(27) 119.8 C(22)-C(27)-H(27) 119.8 O(3)-C(28)-O(2) 126.06(18) O(3)-C(28)-C(20) 118.79(17) O(2)-C(28)-C(20) 115.13(16) 10

Table 4. Anisotropic displacement parameters (Å 2 x 10 3 ) for 06087. The anisotropic displacement factor exponent takes the form: -2 π 2 [ h 2 a* 2 U 11 +... + 2 h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 Ni(1) 11(1) 16(1) 11(1) -1(1) -1(1) -3(1) Cl(1) 18(1) 19(1) 21(1) -6(1) -4(1) -1(1) O(1) 15(1) 43(1) 27(1) -9(1) -6(1) -4(1) O(2) 15(1) 21(1) 15(1) -2(1) -2(1) -3(1) O(3) 15(1) 21(1) 23(1) -7(1) -4(1) -4(1) N(1) 13(1) 20(1) 14(1) -1(1) -2(1) -3(1) N(2) 13(1) 16(1) 14(1) 0(1) -5(1) -2(1) N(3) 15(1) 15(1) 15(1) -2(1) -2(1) -2(1) C(1) 23(1) 18(1) 14(1) 0(1) 1(1) -1(1) C(2) 39(1) 16(1) 21(1) -1(1) 2(1) -1(1) C(3) 25(1) 25(1) 18(1) -1(1) 4(1) -4(1) C(4) 25(1) 30(1) 21(1) 5(1) -4(1) 3(1) C(5) 11(1) 24(1) 20(1) -2(1) -2(1) -2(1) C(6) 14(1) 23(1) 20(1) 1(1) -3(1) -3(1) C(7) 17(1) 19(1) 13(1) 1(1) -5(1) -3(1) C(8) 15(1) 28(1) 18(1) -2(1) -1(1) -7(1) C(9) 21(1) 22(1) 18(1) -1(1) -6(1) -8(1) C(10) 18(1) 17(1) 13(1) -3(1) -4(1) 0(1) C(11) 14(1) 19(1) 12(1) 1(1) -4(1) -1(1) C(12) 14(1) 17(1) 12(1) 3(1) -5(1) -3(1) C(13) 13(1) 17(1) 12(1) 2(1) -3(1) 1(1) C(14) 15(1) 13(1) 14(1) -3(1) -2(1) -3(1) C(15) 14(1) 25(1) 17(1) -1(1) -5(1) 1(1) C(16) 20(1) 34(1) 13(1) 2(1) -2(1) 0(1) C(17) 14(1) 34(1) 19(1) -1(1) 2(1) 1(1) C(18) 15(1) 29(1) 22(1) 0(1) -5(1) 2(1) C(19) 18(1) 22(1) 15(1) 1(1) -4(1) -2(1) C(20) 14(1) 17(1) 18(1) -2(1) -2(1) -4(1) C(21) 25(1) 18(1) 15(1) 0(1) -2(1) -5(1) C(22) 26(1) 13(1) 19(1) 3(1) -6(1) -2(1) C(23) 32(1) 18(1) 20(1) -1(1) -9(1) 1(1) C(24) 35(1) 24(1) 34(1) 1(1) -21(1) -1(1) C(25) 22(1) 24(1) 38(1) 5(1) -12(1) 2(1) C(26) 27(1) 21(1) 26(1) 2(1) -4(1) 4(1) C(27) 25(1) 20(1) 18(1) 0(1) -6(1) -1(1) C(28) 15(1) 17(1) 18(1) -4(1) -3(1) 2(1) 11

Table 5. Hydrogen coordinates and isotropic displacement parameters for 06087. x y z U(eq) H(3N) 0.730(3) 0.175(2) 0.4746(18) 0.018 H(2A) 0.6691 0.4955 0.5039 0.041 H(2B) 0.7508 0.5454 0.3900 0.041 H(2C) 0.8471 0.4893 0.4651 0.041 H(3A) 0.9676 0.3272 0.3420 0.037 H(3B) 0.8741 0.3764 0.2632 0.037 H(3C) 0.8676 0.2264 0.3027 0.037 H(4A) 0.5899 0.2409 0.3569 0.039 H(4B) 0.5998 0.3914 0.3184 0.039 H(4C) 0.5120 0.3484 0.4326 0.039 H(5A) 0.9506 0.2888 0.4923 0.022 H(5B) 0.8915 0.1591 0.5616 0.022 H(8) 0.7980 0.5508 0.7174 0.025 H(9) 0.6955 0.7073 0.8296 0.024 H(11) 0.3123 0.4983 0.9219 0.018 H(15) 0.3012 0.2093 0.9947 0.022 H(16) 0.0703 0.1982 1.1151 0.027 H(17) -0.1435 0.2770 1.0725 0.028 H(18) -0.1302 0.3608 0.9075 0.027 H(19) 0.0987 0.3712 0.7859 0.022 H(20) 0.2050 0.1318 0.7559 0.020 H(21A) 0.3226 0.0114 0.8607 0.024 H(21B) 0.3258-0.0824 0.7711 0.024 H(23) 0.5448 0.0590 0.9023 0.028 H(24) 0.8040 0.0547 0.8729 0.035 H(25) 0.9505-0.0222 0.7217 0.033 H(26) 0.8360-0.0932 0.6008 0.030 H(27) 0.5772-0.0824 0.6274 0.025 12

Table 6. Torsion angles [ ] for 06087. N(1)-Ni(1)-O(2)-C(28) 80(13) N(2)-Ni(1)-O(2)-C(28) -15.81(13) N(3)-Ni(1)-O(2)-C(28) 160.56(13) N(2)-Ni(1)-N(1)-C(6) 151.45(14) O(2)-Ni(1)-N(1)-C(6) 56(13) N(3)-Ni(1)-N(1)-C(6) -24.92(14) N(2)-Ni(1)-N(1)-C(7) -30.21(15) O(2)-Ni(1)-N(1)-C(7) -126(13) N(3)-Ni(1)-N(1)-C(7) 153.42(15) N(1)-Ni(1)-N(2)-C(13) 21.38(17) O(2)-Ni(1)-N(2)-C(13) -158.92(17) N(3)-Ni(1)-N(2)-C(13) 111.9(11) N(1)-Ni(1)-N(2)-C(20) -155.26(12) O(2)-Ni(1)-N(2)-C(20) 24.44(12) N(3)-Ni(1)-N(2)-C(20) -64.8(11) N(1)-Ni(1)-N(3)-C(5) 32.10(12) N(2)-Ni(1)-N(3)-C(5) -58.6(11) O(2)-Ni(1)-N(3)-C(5) -147.60(12) N(1)-Ni(1)-N(3)-C(1) -95.74(14) N(2)-Ni(1)-N(3)-C(1) 173.5(10) O(2)-Ni(1)-N(3)-C(1) 84.56(14) C(5)-N(3)-C(1)-C(4) -177.40(16) Ni(1)-N(3)-C(1)-C(4) -54.27(19) C(5)-N(3)-C(1)-C(2) -57.3(2) Ni(1)-N(3)-C(1)-C(2) 65.85(19) C(5)-N(3)-C(1)-C(3) 64.7(2) Ni(1)-N(3)-C(1)-C(3) -172.12(13) C(1)-N(3)-C(5)-C(6) 96.75(19) Ni(1)-N(3)-C(5)-C(6) -33.55(17) C(7)-N(1)-C(6)-O(1) 12.8(3) Ni(1)-N(1)-C(6)-O(1) -168.81(18) C(7)-N(1)-C(6)-C(5) -168.48(16) Ni(1)-N(1)-C(6)-C(5) 9.9(2) N(3)-C(5)-C(6)-O(1) -164.11(18) N(3)-C(5)-C(6)-N(1) 17.1(2) C(6)-N(1)-C(7)-C(8) 26.0(3) Ni(1)-N(1)-C(7)-C(8) -152.26(15) C(6)-N(1)-C(7)-C(12) -158.41(18) Ni(1)-N(1)-C(7)-C(12) 23.4(2) N(1)-C(7)-C(8)-C(9) 175.61(18) C(12)-C(7)-C(8)-C(9) -0.2(3) C(7)-C(8)-C(9)-C(10) 2.4(3) C(8)-C(9)-C(10)-C(11) -2.3(3) C(8)-C(9)-C(10)-Cl(1) 178.17(15) C(9)-C(10)-C(11)-C(12) 0.0(3) 13 Cl(1)-C(10)-C(11)-C(12) 179.46(14) C(10)-C(11)-C(12)-C(7) 2.3(3) C(10)-C(11)-C(12)-C(13) -177.75(17) N(1)-C(7)-C(12)-C(11) -177.95(16) C(8)-C(7)-C(12)-C(11) -2.2(3) N(1)-C(7)-C(12)-C(13) 2.1(3) C(8)-C(7)-C(12)-C(13) 177.88(17) C(20)-N(2)-C(13)-C(12) 172.01(16) Ni(1)-N(2)-C(13)-C(12) -4.3(3) C(20)-N(2)-C(13)-C(14) -11.6(3) Ni(1)-N(2)-C(13)-C(14) 172.16(13) C(11)-C(12)-C(13)-N(2) 167.87(17) C(7)-C(12)-C(13)-N(2) -12.2(3) C(11)-C(12)-C(13)-C(14) -8.6(2) C(7)-C(12)-C(13)-C(14) 171.28(16) N(2)-C(13)-C(14)-C(15) 106.8(2) C(12)-C(13)-C(14)-C(15) -76.6(2) N(2)-C(13)-C(14)-C(19) -75.1(2) C(12)-C(13)-C(14)-C(19) 101.5(2) C(19)-C(14)-C(15)-C(16) -1.0(3) C(13)-C(14)-C(15)-C(16) 177.04(18) C(14)-C(15)-C(16)-C(17) -0.2(3) C(15)-C(16)-C(17)-C(18) 1.2(3) C(16)-C(17)-C(18)-C(19) -0.9(3) C(17)-C(18)-C(19)-C(14) -0.3(3) C(15)-C(14)-C(19)-C(18) 1.3(3) C(13)-C(14)-C(19)-C(18) -176.83(18) C(13)-N(2)-C(20)-C(28) 155.64(17) Ni(1)-N(2)-C(20)-C(28) -27.44(17) C(13)-N(2)-C(20)-C(21) -83.5(2) Ni(1)-N(2)-C(20)-C(21) 93.44(15) N(2)-C(20)-C(21)-C(22) -43.1(2) C(28)-C(20)-C(21)-C(22) 75.5(2) C(20)-C(21)-C(22)-C(23) 105.0(2) C(20)-C(21)-C(22)-C(27) -73.1(2) C(27)-C(22)-C(23)-C(24) 0.8(3) C(21)-C(22)-C(23)-C(24) -177.38(18) C(22)-C(23)-C(24)-C(25) -1.1(3) C(23)-C(24)-C(25)-C(26) 0.2(3) C(24)-C(25)-C(26)-C(27) 1.0(3) C(25)-C(26)-C(27)-C(22) -1.3(3) C(23)-C(22)-C(27)-C(26) 0.3(3) C(21)-C(22)-C(27)-C(26) 178.51(18) Ni(1)-O(2)-C(28)-O(3) -175.89(16) Ni(1)-O(2)-C(28)-C(20) 2.6(2)

N(2)-C(20)-C(28)-O(3) -165.04(17) C(21)-C(20)-C(28)-O(3) 74.8(2) N(2)-C(20)-C(28)-O(2) 16.3(2) C(21)-C(20)-C(28)-O(2) -103.83(19) 14

11.4995 8.6555 8.6522 8.6260 8.6222 7.7548 7.6541 7.6217 7.5348 7.5034 7.2975 7.2196 7.2159 7.1933 7.1906 7.1688 7.1650 1.28 1.00 2.17 3.72 2.81 1.40 2.69 4.0586 12.0 11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 f1 (ppm) 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

11.3316 8.6109 8.5788 7.7763 7.6479 7.5845 7.5545 7.5276 7.2978 0.98 1.00 2.12 1.40 4.53 2.41 4.0519 12.0 11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 f1 (ppm) 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0-0.5

11.6914 8.7045 8.6770 7.8027 7.5774 7.5645 7.5550 7.5289 7.5047 7.4655 7.4435 7.3467 7.3395 7.3184 7.2941 7.2876 7.2650 7.1714 7.1474 7.1232 1.10 1.00 1.92 7.54 3.24 1.17 2.55 2.52 3.9023 3.4931 12.5 12.0 11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 f1 (ppm) 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0-0.5

1.18 1.00 2.12 5.73 1.18 2.54 1.14 1.19 7.72 11.6462 8.6927 8.6650 7.7801 7.5422 7.5297 7.4854 7.4586 7.1301 7.1050 7.0795 3.4246 2.8819 2.8610 2.8401 2.8193 2.7986 1.7704 1.1396 1.1188 12.5 12.0 11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 f1 (ppm) 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0-0.5

0.93 1.00 1.78 5.36 1.06 2.13 1.49 9.80 11.7179 8.7047 8.7020 8.6768 8.6741 7.7777 7.6168 7.5843 7.5301 7.4820 7.2980 7.1525 7.1488 7.1269 7.1241 7.1019 7.0982 3.4049 1.6516 1.1725 12.5 12.0 11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 f1 (ppm) 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0-0.5

0.83 0.81 1.66 4.59 0.95 2.05 2.00 4.13 12.16 11.5873 8.6298 8.6020 7.6372 7.6004 7.5755 7.5240 7.4686 7.1489 7.1453 7.1231 7.1209 7.0984 7.0948 3.4660 2.0405 1.6794 1.6721 1.6204 1.5747 1.5345 13.5 13.0 12.5 12.0 11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 f1 (ppm) 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0-0.5-1.0

11.6049 8.6713 8.6417 7.8079 7.6520 7.5648 7.5280 7.4836 7.2976 0.85 1.02 1.81 1.04 2.61 0.70 1.99 8.75 3.4063 1.1711 13.5 13.0 12.5 12.0 11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 f1 (ppm) 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0-0.5-1.0

1.00 3.07 5.88 1.23 1.06 1.09 1.20 1.11 1.25 1.99 1.25 1.20 1.24 8.6500 8.6218 7.4490 7.4281 7.4048 7.3828 7.3556 7.2969 7.1895 7.1663 7.0334 6.9571 6.9309 6.8589 6.8352 6.8091 4.4684 4.4225 4.0090 3.9733 3.9279 3.7947 3.6595 3.6363 3.2798 3.2236 3.0827 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

1.00 2.79 1.06 1.21 0.99 0.91 0.97 1.02 1.06 1.97 1.07 1.10 1.01 5.45 3.34 8.5693 8.5406 7.5618 7.4117 7.3884 7.3776 7.3542 7.2097 7.1830 7.0175 7.0101 6.9992 6.9507 6.9456 6.9234 6.9182 6.8557 6.8321 6.8084 4.0329 4.0076 3.9765 3.9514 3.7486 3.3223 3.1540 3.1320 3.1140 3.0927 2.7990 1.6729 1.6511 1.5707 1.5489 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

1.00 2.85 2.72 2.91 1.02 1.96 1.06 1.01 1.36 8.81 8.3917 8.3654 7.5853 7.5532 7.4055 7.3769 7.3483 7.2241 6.9856 6.9749 6.9429 6.9374 6.9155 6.9100 6.8625 6.8596 6.8360 6.8121 6.8091 4.2098 4.1847 4.1535 4.1284 3.7157 3.4282 3.3718 2.6622 1.6668 1.6004 1.5366 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

1.00 3.24 1.20 1.05 1.05 1.02 1.08 1.06 2.26 1.13 1.08 4.53 5.61 6.55 2522.2911 2514.4141 2513.7669 2266.6036 2253.3189 2245.3507 2205.9293 2195.8302 2165.3644 2087.9250 2075.4443 2073.9627 2067.2576 2065.8097 2048.3728 2047.4216 2040.3670 2033.2638 2032.2391 1234.8591 1227.2592 1217.8315 1210.2588 1116.9020 1093.5143 1040.3214 1023.2776 914.4214 907.0227 652.0183 634.1806 512.0982 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

1.00 3.16 1.66 1.03 1.00 0.88 1.07 1.82 1.08 1.03 8.67 8.3953 8.3649 7.5724 7.5630 7.5536 7.5462 7.2107 6.9781 6.9718 6.9628 6.9497 6.8573 6.8489 4.1971 4.1722 4.1404 4.1155 3.6703 3.3871 3.3302 2.9820 1.5667 1.5114 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

1.00 6.47 3.34 1.47 1.14 0.81 1.06 1.12 2.22 1.11 1.27 10.08 8.2733 8.2430 7.6284 7.6051 7.5812 7.5610 7.4052 7.2894 7.1437 7.1157 6.7730 6.7646 4.3246 4.3148 4.3061 4.2962 3.3943 3.3696 3.3389 3.3142 3.0632 2.9752 2.6734 2.6546 2.6283 2.6095 1.9626 1.9384 1.2886 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 f1 (ppm) 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

1.00 6.25 4.81 1.12 1.96 0.98 1.05 2.09 1.00 3.43 6.92 1.49 6.53 8.2959 8.2677 7.5929 7.3982 7.3471 7.3310 7.2980 7.1249 6.8385 6.8264 4.3203 4.3123 3.1594 3.1035 3.0938 3.0848 3.0481 3.0399 2.6973 2.6788 2.6526 2.6339 2.1095 1.9489 1.8770 1.7818 1.7591 1.6865 1.6422 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 f1 (ppm) 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0-0.5

1.00 2.22 3.44 5.95 2.33 2.12 1.14 1.05 1.11 1.13 1.25 2.41 3.45 6.62 6.62 8.3738 8.3456 7.6637 7.5459 7.5109 7.3895 7.3476 7.2978 7.0418 6.8283 6.8264 6.8134 6.7265 6.6736 4.1943 4.1830 4.1761 4.1648 3.2430 3.2197 3.1872 3.1641 3.1200 3.0643 2.6461 2.6104 2.3291 2.1370 1.8936 1.6661 1.6223 1.2836 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0-0.5

1.00 3.09 2.11 1.05 1.98 1.17 1.03 1.17 0.87 1.22 1.07 0.81 2.99 5.88 6.38 8.3778 8.3497 7.5560 7.5211 7.4066 7.3778 7.3488 7.2981 7.0481 6.8264 6.8168 6.8078 4.2427 4.2180 4.1875 4.1628 4.0699 4.0612 4.0500 4.0412 3.7681 3.5697 3.5144 2.7867 2.7097 2.6619 2.6441 2.5554 2.3267 2.2613 2.2407 2.0875 1.7341 1.6363 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0-0.5

1.00 4.32 3.30 6.83 3.15 2.14 1.06 1.06 1.08 1.09 1.11 1.09 2.14 1.11 3.36 6.95 7.88 2483.5522 2475.1619 2287.6790 2214.8635 2200.1619 2189.0202 2178.4657 2094.1251 2048.2991 2043.0628 2040.4128 2037.6456 1559.5534 1555.9391 1550.9423 1547.3353 1380.5338 1371.8113 1340.0343 1335.3444 1251.8105 1243.0038 1128.7672 1110.8593 1044.5302 990.7857 983.6357 974.2004 967.1139 933.7103 917.1798 659.6684 632.1476 556.2503 491.4952 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 f1 (ppm) 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

NHtbutylMichaelwithipropyl 10 1 "C:\Users\Ellis\My NMR Files\ICON-NMR Data" PROTON [rel] 0 2 4 6 8 10 12 14 8 6 4 2 [ppm]

NHtbutylmichaelwithalphanaphthyl 10 1 "C:\Users\Ellis\My NMR Files\ICON-NMR Data" PROTON [rel] 0 2 4 6 8 10 12 14 8 6 4 2 [ppm]

NHtButlymichaelwith4CF3Ph 10 1 "C:\Users\Hubin\My NMR Files\ICON-NMR Data" PROTON [rel] 0 2 4 6 8 10 12 14 8 6 4 2 [ppm]

NHtbutylMichaelwith4OMePH 10 1 "C:\Users\Ellis\My NMR Files\ICON-NMR Data" PROTON [rel] - 0 1 2 3 8 6 4 2 [ppm]

0.95 2.04 4.98 7.39 3.01 2.06 1.00 1.12 1.04 1.08 1.11 4.42 3.37 1.16 6.69 6.46 8.3241 8.2961 7.8073 7.7804 7.4612 7.3071 7.2190 6.9527 6.8019 6.8005 6.7905 6.7849 5.2130 5.2001 5.1841 5.1713 4.6280 4.5986 4.5693 4.3976 4.1843 4.0223 3.9983 3.9664 3.3363 3.9427 3.3131 3.2798 3.2575 3.2233 3.2018 3.1841 3.1285 2.1858 2.1001 2.0222 2.0022 1.8702 1.6324 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

1.03 4.18 3.16 2.15 2.17 1.31 2.04 2.03 4.08 1.00 1.03 0.99 1.05 1.00 2.08 1.06 3.25 1.89 6.28 6.14 8.2727 8.2445 8.0161 7.5878 7.9421 7.3881 7.3630 7.3258 7.3041 7.2827 7.1555 7.1243 7.0303 6.9797 6.8677 6.8445 6.8163 6.7630 5.2006 5.1881 5.1719 5.1594 4.6142 4.5850 4.5559 4.4679 4.4542 4.1304 4.1011 4.0439 3.9916 3.4825 3.4584 3.4294 3.3800 3.3555 2.6596 2.6039 1.8925 2.0432 1.7263 1.5789 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

1.00 1.14 1.20 8.62 2.15 3.18 2.14 1.02 1.06 1.04 1.11 3.12 1.10 1.15 3.20 3.39 7.11 7.45 8.2528 8.2251 7.5383 7.4340 7.3286 7.2975 7.2739 7.1295 7.0172 6.9858 6.8249 6.8055 6.7981 6.7852 5.2032 5.1913 5.1745 5.1626 4.6231 4.5939 4.5650 4.4047 4.1367 3.9204 3.6677 3.2653 3.2413 3.2311 3.2062 3.1896 3.1649 3.1094 2.1930 2.1108 1.8672 1.6824 1.6408 1.2830 1.2626 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0

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