Synthesis, Crystal Structure and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5- yl)benzenes

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Supplementary information Synthesis, Crystal Structure and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5- yl)benzenes Marcos A. P. Martins 1 *, Alexandre R. Meyer 1, Paulo R. S. Salbego 1, Daniel M. dos Santos 1, Guilherme A. de Moraes 2, Helio G. Bonacorso 1, Nilo Zanatta 1, Manfredo Hörner 2 1 Núcleo de Química de Heterociclos (NUQUIMHE), Department of Chemistry, Federal University of Santa Maria (UFSM), 97105-900, Santa Maria, RS, Brazil 2 Núcleo de Investigação de Triazenos e Complexos (NITRICO), Department of Chemistry, Federal University of Santa Maria (UFSM), 97105-900, Santa Maria, RS, Brazil * Correspondence: marcos.nuquimhe@gmail.com Tel.: +55 (55) 3220 8756 Figure S1. 1D arrangement for compound 9b.

(a) (b) (c) Figure S2. BCPs for the dimers involved in the 1D arrangement for compounds 5 (a), 7 (b), and 9b (c, d). (d)

Table S1. Data collection and structure refinement for structures 5, 7 and 9b. Compound (5) (7) (9b) Crystal data Chemical formula C33 H24 N6 C33 H18 Cl6 N6 C33 H21 Br3 N6 CCDC number 1501480 1484377 1484578 Mr 504.58 711.23 741.26 Crystal system, space group Monoclinic, P 21/n Monoclinic, P 21/n Temperature (K) 293 293 293 a, b, c (Å) 8.811(7), 31.67(2), 9.691(9) 10.3914(2), 31.6622(2), 10.5723(2) α, β, γ ( ) 90, 97.85, 90 90, 110.8580(10), 90 Triclinic, P1 V (Å 3 ) 2679(4) 3250.48(12) 1513.74(8) Z 4 4 2 F(000) 1056 1440 732 Dx (Mg m 3 ) 1.251 1.453 1.626 Radiation type Mo Kα Mo Kα Mo Kα µ (mm 1 ) 0.076 0.56 4.03 Crystal size (mm) Data collection 0.434 x 0.233 x 0.084 8.7732(3), 10.8040(3), 16.7315(5) 76.0570(10), 87.256(2), 79.5720(10) 0.520 x 0.490 x 0.220 0.506 x 0.210 x 0.164 Diffractometer X8 APEX II X8 APEX II X8 APEX II Absorption correction (Coppens et al., 1965) Gaussian Gaussian Gaussian Tmin, Tmax 0.980, 0.994 0.873, 0.908 0.435, 0.639 Reflections collected, unique 44903, 5466 50606, 7215 39956, 6708 Rint 0.123 0.035 0.052 θmax ( ) 26.52 27.16 27.18 Refinement R[F 2 > 2σ(F 2 )], wr(f 2 ), S 0.061, 0.110, 1.00 0.082, 0.249, 1.06 0.039, 0.087, 1.02 N. of reflections 5466 7215 6708 N. of parameters 353 406 379 Δρmax, Δρmin (e Å 3 ) 0.173, 0.190 2.563ª, 0.408 0.440,-0.749 a Highest peak: 2,536 (e Å -3 ) at 0.6044, -0.0557, 0.8186 [0.761 Å from H16C].

Table S2. QTAIM data of intramolecular interactions of compounds 5, 7, and 9b. ρ Comp. Interaction 2 ρ G (a.u.) (a.u.) (a.u.) CHB πph +0.001709 +0.005703 +0.001064-0.000703 +7.029502 +1.348943 5 CHB πph +0.002334 +0.007711 +0.001482-0.001036 +6.764544 +0.735388 CHB πbz +0.008895 +0.036788 +0.006966-0.004735 +5.741479 +0.940599 V (a.u) BPL (Å) ε 7 9b CHA ClC +0.002861 +0.009384 +0.001869-0.001392 +6.295619 +0.069233 ClB πpha +0.006076 +0.017295 +0.003573-0.002822 +6.775708 +1.182899 ClA πphc +0.006672 +0.019205 +0.003951-0.003100 +6.850917 +1.548697 ClC πphb +0.007134 +0.021533 +0.004408-0.003432 +6.503711 +1.295082 CHB πphc +0.002607 +0.008188 +0.001588-0.001129 +6.239854 +0.810114 BrC πpha +0.003151 +0.007538 +0.001608-0.001331 +7.876611 +1.152721 CHB πphc +0.003635 +0.012417 +0.002331-0.001559 +5.851308 +0.247889 BrA πphb +0.004203 +0.010958 +0.002338-0.001936 +7.214326 +2.528119

Table S3. Geometric data of intramolecular interactions of compounds 5, 7, and 9b. Comp. Molecular Structure Intramolecular Interaction Atom-atom distance (Å) Interaction angle ( ) Atomcentroid distance (Å) I CHB πph 3.448 130.56 4.213 5 III I II II CHB πph III CHB πbz 3.362 129.51 3.411 2.684 108.43 3.218 I CHA ClC 3.294 156.89-7 IV I II II ClB πpha III ClA πphc 3.445 131.58 3.609 3.469 141.54 3.688 III IV ClC πphb 3.377 142.53 3.456 III I BrC πpha 4.006 123.71 4.326 9b IV I II II BrA πphb III CHB πphc IV CHB πphc 3.778 151.45 3.789 2.993 142.63 3.788 3.252 135.12 3.560

Table S4. QTAIM data of intermolecular interactions for the dimers involved in the 1D arrangement for compounds 5 (a), 7 (b), and 9b (c, d). ρ 2ρ K V G Comp. Interaction ε (au) (a.u.) (a.u.) (a.u.) (a.u.) 5 7 9b (dimer 1) 9b (dimer 2) C13C-H13C H4C-C4C 0.000625 +0.002109 0.385237-0.000166-0.000196 +0.000361 7.917284 C14C-H14C H13A-C13A 0.001150 +0.003850 10.87582-0.000286-0.000391 +0.000677 7.159302 C4A-H4A H13A-C13A 0.001691 +0.007862 0.228573-0.000606-0.000753 +0.001359 5.405544 C15B-H15B C3B-H3B 0.001810 +0.008470 0.069926-0.000649-0.000820 +0.001469 5.340153 C3A-H3A H14A-C14A 0.002610 +0.010479 1.451658-0.000755-0.001110 +0.001865 5.903538 C14C-H14C C51B(π) 0.003203 +0.009717 0.835703-0.000487-0.001455 +0.001942 6.392775 C15C-H15C H4B-C4B 0.003941 +0.016360 0.367039-0.001078-0.001934 +0.003012 5.003101 Total 0.015030 C4A-H4A Cl2C 0.002102 +0.007701 0.396783-0.000507-0.000912 +0.001418 6.755820 C3A-H3A Cl2A 0.002453 +0.008534 0.872875-0.000557-0.001020 +0.001577 7.028604 Cl2B C51A(πBz) 0.005733 +0.016697 2.503532-0.000721-0.002732 +0.003453 7.029595 Total 0.010288 C14C-H14C N2B 0.001974 +0.008350 0.064986-0.000589-0.000909 +0.001498 6.305415 C14C-H14C N2B 0.001974 +0.008349 0.065009-0.000589-0.000909 +0.001498 6.305415 C15B-H15B N2B 0.003039 +0.012084 0.473979-0.000777-0.001467 +0.002244 6.126470 C15B-H15B N2B 0.003039 +0.012084 0.473798-0.000777-0.001467 +0.002244 6.126470 C15C-H15C C12B 0.003828 +0.013741 0.602985-0.000879-0.001678 +0.002557 6.014947 C16B C16B 0.003576 +0.008290 3.038742-0.000278-0.001517 +0.001795 7.049161 C15C-H15C C12B 0.003827 +0.013740 0.603086-0.000879-0.001678 +0.002556 6.015115 Total 0.021257 C13A-H13A Br3C 0.004336 +0.015844 0.238205-0.000914-0.002133 +0.003047 6.078877 C13A-H13A Br3C 0.004336 +0.015844 0.238206-0.000914-0.002133 +0.003047 6.078877 C14A-H14A Br3C 0.003426 +0.011924 1.270349-0.000714-0.001553 +0.002267 6.625252 C14A-H14A Br3C 0.003426 +0.011924 1.270401-0.000714-0.001553 +0.002267 6.625252 Total 0.015524 BPL (Å)

Figure S3. 1 H NMR spectrum of 1,3,5-tris(1-phenyl-1H-pyrazol-5-yl)benzene 5. Figure S4. 13 C NMR spectrum of 1,3,5-tris(1-phenyl-1H-pyrazol-5-yl)benzene 5.

Figure S5. 1 H NMR spectrum of 1,3,5-tris(1-(2,4-difluorophenyl)-1H-pyrazol-5-yl)benzene 6. Figure S6. 13 C NMR spectrum of 1,3,5-tris(1-(2,4-difluorophenyl)-1H-pyrazol-5-yl)benzene 6.

Figure S7. 1 H NMR spectrum of 1,3,5-tris(1-(2,4-dichlorophenyl)-1H-pyrazol-5-yl)benzene 7. Figure S8. 13 C NMR spectrum of 1,3,5-tris(1-(2,4-dichlorophenyl)-1H-pyrazol-5-yl)benzene 7.

Figure S9. 1 H NMR spectrum of 1,3,5-tris(4-chloro-1-phenyl-1H-pyrazol-5-yl)benzene 9a. Figure S10. 13 C NMR spectrum of 1,3,5-tris(4-chloro-1-phenyl-1H-pyrazol-5-yl)benzene 9a.

Figure S11. 1 H NMR spectrum of 1,3,5-tris(4-bromo-1-phenyl-1H-pyrazol-5-yl)benzene 9b. Figure S12. 13 C NMR spectrum of 1,3,5-tris(4-bromo-1-phenyl-1H-pyrazol-5-yl)benzene 9b.

Figure S13. 1 H NMR spectrum of 1,3,5-tris(4-iodo-1-phenyl-1H-pyrazol-5-yl)benzene 9c. Figure S14. 13 C NMR spectrum of 1,3,5-tris(4-iodo-1-phenyl-1H-pyrazol-5-yl)benzene 9c.

Figure S15. 1 H NMR spectrum of 1,3,5-tris(4-chloro-1-(2,4-difluorophenyl)-1H-pyrazol-5- yl)benzene 10a. Figure S16. 13 C NMR spectrum of 1,3,5-tris(4-chloro-1-(2,4-difluorophenyl)-1H-pyrazol-5- yl)benzene 10a.

Figure S17. 1 H NMR spectrum of 1,3,5-tris(4-bromo-1-(2,4-difluorophenyl)-1H-pyrazol-5- yl)benzene 10b. Figure S18. 13 C NMR spectrum of 1,3,5-tris(4-bromo-1-(2,4-difluorophenyl)-1H-pyrazol-5- yl)benzene 10b.

Figure S19. 1 H NMR spectrum of 1,3,5-tris(4-iodo-1-(2,4-difluorophenyl)-1H-pyrazol-5- yl)benzene 10c. Figure S20. 13 C NMR spectrum of 1,3,5-tris(4-iodo-1-(2,4-difluorophenyl)-1H-pyrazol-5- yl)benzene 10c.

Figure S21. 1 H NMR spectrum of 1,3,5-tris(4-chloro-1-(2,4-dichlorophenyl)-1H-pyrazol-5- yl)benzene 11a. Figure S22. 13 C NMR spectrum of 1,3,5-tris(4-chloro-1-(2,4-dichlorophenyl)-1H-pyrazol-5- yl)benzene 11a.

Figure S23. 1 H NMR spectrum of 1,3,5-tris(4-Bromo-1-(2,4-dichlorophenyl)-1H-pyrazol-5- yl)benzene 11b. Figure S24. 13 C NMR spectrum of 1,3,5-tris(4-Bromo-1-(2,4-dichlorophenyl)-1H-pyrazol-5- yl)benzene 11b.

Figure S25. 1 H NMR spectrum of 1,3,5-tris(4-iodo-1-(2,4-dichlorophenyl)-1H-pyrazol-5- yl)benzene 11c. Figure S26. 13 C NMR spectrum of 1,3,5-tris(4-iodo-1-(2,4-dichlorophenyl)-1H-pyrazol-5- yl)benzene 11c.

Figure S27. LCMS spectra NMR spectrum of 1,3,5-tris(1-phenyl-1H-pyrazol-5-yl)benzene 5. Figure S28. LCMS spectra of 1,3,5-tris(1-(2,4-difluorophenyl)-1H-pyrazol-5-yl)benzene 6. Figure S29. LCMS spectra of 1,3,5-tris(1-(2,4-dichlorophenyl)-1H-pyrazol-5-yl)benzene 7.

Figure S30. LCMS spectra of 1,3,5-tris(4-chloro-1-phenyl-1H-pyrazol-5-yl)benzene 9a. Figure S31. LCMS spectra of 1,3,5-tris(4-bromo-1-phenyl-1H-pyrazol-5-yl)benzene 9b. Figure S32. LCMS spectra of 1,3,5-tris(4-iodo-1-phenyl-1H-pyrazol-5-yl)benzene 9c.

Figure S33. LCMS spectra of 1,3,5-tris(4-chloro-1-(2,4-difluorophenyl)-1H-pyrazol-5-yl)benzene 10a. Figure S34. LCMS spectra of 1,3,5-tris(4-bromo-1-(2,4-difluorophenyl)-1H-pyrazol-5-yl)benzene 10b. Figure S35. LCMS spectra of 1,3,5-tris(4-iodo-1-(2,4-difluorophenyl)-1H-pyrazol-5-yl)benzene 10c.

Figure S36. LCMS spectra of 1,3,5-tris(4-chloro-1-(2,4-dichlorophenyl)-1H-pyrazol-5-yl)benzene 11a. Figure S37. LCMS spectra of 1,3,5-tris(4-Bromo-1-(2,4-dichlorophenyl)-1H-pyrazol-5-yl)benzene 11b. Figure S38. LCMS spectra of 1,3,5-tris(4-iodo-1-(2,4-dichlorophenyl)-1H-pyrazol-5-yl)benzene 11c.

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