Supplementary Information
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1 Supplementary Information Eco-Friendly Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones Catalyzed by FeCl 3 /Al 2 O 3 and Analysis of Large 1 H NMR Diastereotopic Effect Isabel Monreal, a Mariano Sánchez-Castellanos, b Karla Ramírez-Gualito, c Gabriel Cuevas, d Karla A. Espinoza a and Ignacio A. Rivero *,a a Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, Tijuana, B.C., Mexico b Facultad de Química de la Universidad Autónoma de México (UNAM), Circuito Exterior s/n, Ciudad Universitaria, Mexico City, Mexico c Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Circuito Exterior s/n, Ciudad Universitaria, Mexico City, Mexico d Centro de Nanociencias y Micro y Nanotecnologías, Instituto Politécnico Nacional, Av. Luis Enrique Erro s/n, Unidad Profesional Adolfo López Mateos, Zacatenco, Mexico City, Mexico Spectroscopy data for 2,3-dihydroquinazolin-4(1H)-ones (3a-3i) 3-Benzyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3a) 1 White solid; yield 98%; mp C; Rf = 0.84 (DCM); IR (ATR) ν / cm (N H), 1631 (C=O), 1617 (=C H); 1 H NMR (200 MHz, CDCl 3 ) δ (m, 1H, Ar H), (m, 11H, Ar H), (m, 2H, Ar H), (d, J 8 Hz, 1H, Ar H), 4.54 (s, 1H, NH), (d, J 15 Hz, 2H, CH 2 ); 13 C NMR (50 MHz, CDCl 3 ) δ 163.2, 145.1, 139.3, 136.7, 133.6, 129.3, 128.9, 128.7, 128.6, 128.0, 127.4, 126.5, 119.1, 115.6, 114.3, 71.0, Benzyl-2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3b) 2 Beige solid; yield 98%; mp C; Rf = 0.50 (DCM); IR (ATR) ν / cm (N H), 3215 (O H), 1614 (C=O), 1592 (N H); 1 H NMR (200 MHz, CDCl 3 ) δ 9.58 (s, 1H, OH), (m, 13H, Ar H), 5.61 (s, H, CH), (d, J 16 Hz, 1H, CH 2 ), (d, J 16 Hz, 1H, CH 2 ); 13 C NMR (50 MHz, CDCl 3 ) δ 162.4, 157.6, 146.5, 137.5, 133.3, 130.7, 128.4, 127.6, 127.5, 127.4, 127.0, 117.0, 115.1, 114.4, 114.3, 69.8, 46.7; MS m/z C 21 H 18 N 2 O 2 [M] + : * irivero@tectijuana.mx
2 3-Benzyl-2-(3-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3c) 3 White solid; yield: 97%; mp C; Rf = 0.27 (DCM); IR (ATR) ν / cm (N H), 3227 (O H), 1607 (C=O), 1591 (N H); 1 H NMR (200 MHz, CDCl 3 ) δ 9.58 (s, 1H, OH), (m, 13H, Ar H), 5.61 (s, H, CH), (d, J 16 Hz, 1H, CH 2 ) (d, J 16 Hz, 1H, CH 2 ); 13 C NMR (50 MHz, CDCl 3 ) δ 162.3, 157.6, 146.3, 142.1, 137.5, 133.4, 129.6, 128.5, 127.6, 127.5, 127.2, 117.1, 116.8, 115.4, 114.5, 114.3, 112.9, 69.7, 47.0; MS m/z C 21 H 18 N 2 O 2 [M] + : Benzyl-2-(2,4-dihydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3d) 4 Beige solid; yield: 95%; mp: C; Rf = 0.55 (DCM); IR (ATR) ν / cm (N H amina), 3152 (O H fenol), 1609 (C=O), 1567 (N H); 1 H NMR (200 MHz, CDCl 3 ) δ 9.54 (s, 2H, OH), (m, 13H, Ar H), 5.62 (s, H, CH), (d, J 16 Hz, 1H, CH 2 ) (d, J 16 Hz, 1H, CH 2 ); 13 C NMR (50 MHz, CDCl 3 ) δ 162.5, 157.7, 146.6, 137.6, 133.4, 130.8, 128.4, 127.6, 127.6, 127.4, 127.1, 117.1, 115.2, 114.5, 114.3, 69.8, 46.8; MS m/z C 21 H 18 N 2 O 3 [M H] + : Benzyl-2-(2-hydroxynaphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one (3e) 4 Yellow solid; yield: 85%; mp C; Rf = 0.46 (DCM); IR (ATR) ν / cm (N H), 3219 (O H), 1648 (C=O), 1615 (N H); 1 H NMR (200 MHz, CDCl 3 ) δ (s, 1H, OH), (d, J 8 Hz, 1H, NH), (m, 15H, Ar H), 5.75 (s, H, CH), (d, J 16 Hz, 1H, CH 2 ), (d, J 16 Hz, 1H, CH 2 ); 13 C NMR (50 MHz, CDCl 3 ) δ 164.2, 155.0, 148.8, 137.6, 133.4, 133.1, 131.4, 128.6, 128.5, 128.2, 128.0, 127.5, 126.7, 126.3, 124.2, 124.2, 122.8, 118.1, 117.1, 114.5, 114.0, 64.7, 45.8; MS m/z C 25 H 20 N 2 O 2 [M] + : Benzyl-2-(4-(dimethylamino)cyclohexa-1,3-dien-1-yl)-2,3-dihydroquinazolin-4(1H)-one (3f) 5 White solid; yield 95%; mp C; Rf = 0.55 (DCM); IR (ATR) ν / cm (N H), 1633 (C=O), 1606 (N H); 1 H NMR (200 MHz, CDCl 3 ) δ 7.89 (d, J 8 Hz, 1H, NH), (m, 13H, Ar H), 5.54 (s, 1H, CH), (d, J 16 Hz, 1H, CH 2 ), (d, J 16 Hz, 1H, CH 2 ), 3.07 (s, 3H, CH 3 ), 2.91 (s, 3H, CH 3 ); 13 C NMR (50 MHz, CDCl 3 ) δ 162.5, 150.5, 146.6, 137.6, 133.3, 128.5, 127.6, 127.6, 127.4, 127.1, 127.0, 117.0, 114.5, 114.3, 112.1, 69.8, 46.7, 40.0, 40.0; MS m/z C 23 H 23 N 3 O [M] + : Benzyl-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3g) 6 Beige solid; yield: 93%; mp C; Rf = 0.40 (DCM); IR (ATR) ν / cm (N H), 3304 (N H), (OH fenol), 1633 (C=O), 1606 (N H), 1593 (NH), 1129 (C C O); 1 H NMR (200 MHz, CDCl 3 ) δ (m, 12H, Ar H), 5.65 (s, 1H, CH), (d, J 16 Hz, 1H, CH 2 ), (d, J 16 Hz, 1H, CH 2 ), 3.63 (s, 3H, CH 3 ); 13 C NMR (50 MHz, CDCl 3 ) δ 162.7, 147.5, 146.9, 146.7, 137.7, 133.3, 130.9, 128.3, 127.6, 127.3, 127.0, 118.9, 117.2, 115.0, 114.6, 114.3, 110.9, 70.2, 55.3, 46.9; MS m/z C 22 H 20 N 2 O 3 [M] + :
3 3-Benzyl-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3h) 2 White solid; yield 98%; mp C; Rf = 0.24 (DCM); IR (ATR) ν / cm (N H), 1613 (C=O), 1588 (N H); 1 H NMR (200 MHz, CDCl 3 ) δ (m, 13H, Ar H), 5.58 (s, 1H, CH), (d, J 14 Hz, 1H, CH 2 ), (d, J 14 Hz, 1H, CH 2 ), 2.31 (s, 3H, CH 3 ); 13 C NMR (50 MHz, CDCl 3 ) δ 163.3, 146.0, 138.6, 138.6, 136.9, 133.4, 129.2, 128.6, 128.6, 128.4, 128.1, 127.7, 127.2, 126.6, 126.4, 117.8, 114.7, 114.3, 70.4, 46.7, 21.0; MS m/z C 22 H 20 N 2 O [M] + : Benzyl-2-(2,4-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3i) White solid; yield: 97%; mp C; Rf = 0.25 (DCM); IR (ATR) ν / cm (N H), 1641 (C=O), 1607 (N H), (C O C); 1 H NMR (200 MHz, CDCl 3 ) δ (m, 12H, Ar H), 5.88 (s, 1H, CH), (d, J 14.8 Hz, 1H, CH 2 ), (d, J 16 Hz, 1H, CH 2 ), 3.70 (s, 3H, CH 3 ), 3.62 (s, 3H, CH 3 ); 13 C NMR (50 MHz, CDCl 3 ) δ 163.3, 160.6, 157.2, 145.6, 136.7, 132.9, 128.0, 127.7, 127.1, 126.8, 126.7, 118.8, 117.7, 114.7, 114.1, 103.3, 98.3, 64.8, 54.9, 54.8, 46.7; MS m/z C 23 H 22 N 2 O 3 [M] + : General All reagents were purchased in the higher quality available and were used without further purification. The solvents used in column chromatography were obtained from commercial suppliers and used without further distillation. IR spectra were recorded on a PerkinElmer FT-IR 1600 spectrophotometer. Nuclear magnetic resonance 1 H and 13 C spectra at Hz were recorded on a Varian Mercury 200 MHz Spectrometer in CDCl 3 and DMSO-d 6 with TMS as internal standard. Electrospray ionization mass spectra (ESI-MS) were obtained with an ion trap, and the intensities are reported as a percentage relative to the base peak after the corresponding m/z value. The purity was obtained on a High-Pressure Liquid Chromatograph 1090 series II, column HPC-18. Diffraction data were collected on a Smart Apex X-ray diffractometer.
4 Figure S1. IR (ATR) spectrum of 3-benzyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3a).
5 Figure S2. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3a).
6 Figure S3. 13 C NMR spectrum (50 MHz, CDCl 3 ) of 3-benzyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3a).
7 Figure S4. IR (ATR) spectrum of 3-benzyl-2-phenylquinazolin-4(3H)-one (3ax).
8 Figure S5. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-phenylquinazolin-4(3H)-one (3ax).
9 Figure S6. 13 C NMR spectrum (50 MHz, CDCl 3 ) of 3-benzyl-2-phenylquinazolin-4(3H)-one (3ax).
10 Figure S7. IR (ATR) spectrum of 3-benzyl-2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3b).
11 Figure S8. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)- one (3b).
12 Figure S9. 13 C NMR spectrum (50 MHz, CDCl 3 ) of 3-benzyl-2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)- one (3b).
13 Figure S10. MS spectrum of 3-benzyl-2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3b).
14 Figure S11. Fluorescence spectrum of 3-benzyl-2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3b).
15 Figure S12. IR (ATR) spectrum of 3-benzyl-2-(3-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3c).
16 Figure S13. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-(3-hydroxyphenyl)-2,3-dihydroquinazolin- 4(1H)-one (3c).
17 Figure S14. Fluorescence spectrum of 3-benzyl-2-(3-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3c).
18 Figure S15. IR (ATR) spectrum of 3-benzyl-2-(2,4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3d).
19 Figure S16. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-(2,4-hydroxyphenyl)-2,3-dihydroquinazolin- 4(1H)-one (3d).
20 Figure S C NMR spectrum (50 MHz, CDCl 3 ) of 3-benzyl-2-(2,4-hydroxyphenyl)-2,3-dihydroquinazolin- 4(1H)-one (3d).
21 Figure S18. MS spectrum of 3-benzyl-2-(2,4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3d).
22 Figure S19. Fluorescence spectrum of 3-benzyl-2-(2,4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3d).
23 Figure S20. IR (ATR) spectrum of 3-benzyl-2-(2-hydroxynaphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one (3e).
24 Figure S21. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-(2-hydroxynaphthalen-1-yl)-2,3- dihydroquinazolin-4(1h)-one (3e).
25 Figure S C NMR spectrum (50 MHz, CDCl 3 ) of 3-benzyl-2-(2-hydroxynaphthalen-1-yl)-2,3- dihydroquinazolin-4(1h)-one (3e).
26 Figure S23. MS spectrum of 3-benzyl-2-(2-hydroxynaphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one (3e).
27 Figure S24. IR (ATR) spectrum of 3-benzyl-2-(4-(dimethylamino)cyclohexa1,3-dien-1-yl)-2,3-dihydroquinazolin- 4(1H)-one (3f).
28 Figure S25. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-(4-(dimethylamino)cyclohexa1,3-dien-1-yl)-2,3- dihydroquinazolin-4(1h)-one (3f).
29 Figure S C NMR spectrum (50 MHz, CDCl 3 ) of 3-benzyl-2-(4-(dimethylamino)cyclohexa1,3-dien-1-yl)-2,3- dihydroquinazolin-4(1h)-one (3f).
30 Figure S27. MS spectrum of 3-benzyl-2-(4-(dimethylamino)cyclohexa1,3-dien-1-yl)-2,3-dihydroquinazolin- 4(1H)-one (3f).
31 Figure S28. IR (ATR) spectrum of 3-benzyl-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3g).
32 Figure S29. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-(4-hydroxy-3-methoxyphenyl)-2,3- dihydroquinazolin-4(1h)-one (3g).
33 Figure S C NMR spectrum (50 MHz, CDCl 3 ) of 3-benzyl-2-(4-hydroxy-3-methoxyphenyl)-2,3- dihydroquinazolin-4(1h)-one (3g).
34 Figure S31. MS spectrum of 3-benzyl-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3g).
35 Figure S32. Fluorescence spectrum of 3-benzyl-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)- one (3g).
36 Figure S33. IR (ATR) spectrum of 3-benzyl-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3h).
37 Figure S34. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3h).
38 Figure S C NMR spectrum (50 MHz, CDCl 3 ) of 3-benzyl-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3h).
39 Figure S36. MS spectrum of 3-benzyl-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3h).
40 Figure S37. Fluorescence spectrum of 3-benzyl-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3h).
41 Figure S38. IR (ATR) spectrum of 3-benzyl-2-(2,4-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3i).
42 Figure S39. 1 H NMR spectrum (200 MHz, CDCl 3 ) of 3-benzyl-2-(2,4-dimethoxyphenyl)-2,3-dihydroquinazolin- 4(1H)-one (3i).
43 Figure S C NMR spectrum (50 MHz, CDCl 3 ) of 3-benzyl-2-(2,4-dimethoxyphenyl)-2,3-dihydroquinazolin- 4(1H)-one (3i).
44 Figure S41. MS spectrum of 3-benzyl-2-(2,4-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3i).
45 Figure S42. Fluorescence spectrum of 3-benzyl-2-(2,4-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3i).
46 Table S1. Crystal data and structure refinement for 3b Identification code Project Title 152XYZ14 (Solved by: Rubén A. Toscano) E77 Empirical formula C 21 H 18 N 2 O 2 Formula weight Temperature / K 298(2) Wavelength / Å Crystal system orthorhombic Space group P b c a Unit cell dimensions a = (1) Å = 90 b = (2) Å = 90 c = (4) Å = 90 Volume / Å (8) Z 8 Density (calculated) / (Mg m -3 ) Absorption coefficient / mm F(000) 1392 Crystal size / color / shape mm / colorless / prism Theta range for data collection / to Index ranges 13 h 13, 13 k 13, 41 l 41 Reflections collected Independent reflections 3917 [R(int) = ] Completeness to theta = % Measurement device Bruker Smart Apex CCD diffractometer Absorption correction Semi-empirical from equivalents Max. and min. transmission and Refinement method full-matrix least-squares on F 2 Data / restraints / parameters 3917 / 0 / 235 Goodness-of-fit on F
47 Final R indices [I > 2 (I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Extinction coefficient (5) Largest diff. peak and hole / e.å and Table S2. Atomic coordinates ( 10 4 ) and equivalent isotropic displacement parameters (Å ) for 3b. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor x y z U(eq) O(1) 9668(1) 3801(1) 1270(1) 63(1) O(2) 2018(1) 2925(1) 1517(1) 71(1) N(1) 7006(2) 6476(2) 1573(1) 56(1) C(2) 6707(2) 5703(2) 1210(1) 48(1) N(3) 7881(1) 4959(1) 1098(1) 47(1) C(4) 8763(2) 4536(2) 1378(1) 47(1) C(5) 9448(2) 4542(2) 2125(1) 73(1) C(6) 9360(3) 5028(3) 2521(1) 97(1) C(7) 8482(3) 5986(3) 2606(1) 101(1) C(8) 7669(2) 6464(2) 2300(1) 80(1) C(9) 7732(2) 5969(2) 1896(1) 54(1) C(10) 8627(2) 5001(2) 1809(1) 51(1) C(11) 5475(1) 4901(2) 1262(1) 41(1) C(12) 4257(2) 5404(2) 1153(1) 49(1) C(13) 3090(2) 4760(2) 1232(1) 53(1) C(14) 3128(2) 3599(2) 1424(1) 47(1) C(15) 4340(2) 3070(2) 1530(1) 50(1) C(16) 5497(2) 3718(2) 1449(1) 48(1) C(17) 8541(2) 5698(2) 397(1) 49(1) C(18) 9437(2) 6544(2) 558(1) 66(1) C(19) 9955(2) 7506(2) 317(1) 76(1) C(20) 9582(2) 7629(2) -90(1) 80(1) C(21) 8704(3) 6792(3) -256(1) 92(1) C(22) 8177(2) 5835(2) -15(1) 74(1) C(23) 8000(2) 4626(2) 656(1) 56(1)
48 Table S3. Bond lengths and angles for 3b Bond length / Å O(1)-C(4) (19) C(11)-C(16) 1.387(2) O(2)-C(14) (19) C(12)-C(13) 1.382(2) O(2)-H(2A) 0.96(3) C(12)-H(12) N(1)-C(9) 1.375(2) C(13)-C(14) 1.374(2) N(1)-C(2) 1.453(2) C(13)-H(13) N(1)-H(1) 0.88(2) C(14)-C(15) 1.387(2) C(2)-N(3) (19) C(15)-C(16) 1.377(2) C(2)-C(11) 1.514(2) C(15)-H(15) C(2)-H(2) C(16)-H(16) N(3)-C(4) 1.341(2) C(17)-C(18) 1.374(2) N(3)-C(23) 1.462(2) C(17)-C(22) 1.375(2) C(4)-C(10) 1.470(2) C(17)-C(23) 1.507(2) C(5)-C(6) 1.369(3) C(18)-C(19) 1.380(3) C(5)-C(10) 1.395(2) C(18)-H(18) C(5)-H(5) C(19)-C(20) 1.363(3) C(6)-C(7) 1.373(4) C(19)-H(19) C(6)-H(6) C(20)-C(21) 1.359(3) C(7)-C(8) 1.374(4) C(20)-H(20) C(7)-H(7) C(21)-C(22) 1.379(3) C(8)-C(9) 1.398(3) C(21)-H(21) C(8)-H(8) C(22)-H(22) C(9)-C(10) 1.393(2) C(23)-H(23A) C(11)-C(12) 1.384(2) C(23)-H(23B) Bond angle / C(14)-O(2)-H(2A) 110.7(17) C(4)-N(3)-C(23) (14) C(9)-N(1)-C(2) (15) C(4)-N(3)-C(2) (14) C(9)-N(1)-H(1) 117.4(14) C(23)-N(3)-C(2) (13) C(2)-N(1)-H(1) 113.7(14) O(1)-C(4)-N(3) (16) N(1)-C(2)-N(3) (13) O(1)-C(4)-C(10) (15) N(1)-C(2)-C(11) (13) N(3)-C(4)-C(10) (15) N(3)-C(2)-C(11) (13) C(6)-C(5)-C(10) 120.2(2) N(1)-C(2)-H(2) C(6)-C(5)-H(5) N(3)-C(2)-H(2) C(10)-C(5)-H(5) C(11)-C(2)-H(2) C(5)-C(6)-C(7) 120.1(2)
49 C(5)-C(6)-H(6) C(14)-C(15)-H(15) C(7)-C(6)-H(6) C(15)-C(16)-C(11) (14) C(6)-C(7)-C(8) 121.0(2) C(15)-C(16)-H(16) C(6)-C(7)-H(7) C(11)-C(16)-H(16) C(8)-C(7)-H(7) C(18)-C(17)-C(22) (17) C(7)-C(8)-C(9) 119.7(2) C(18)-C(17)-C(23) (15) C(7)-C(8)-H(8) C(22)-C(17)-C(23) (17) C(9)-C(8)-H(8) C(17)-C(18)-C(19) (18) N(1)-C(9)-C(10) (16) C(17)-C(18)-H(18) N(1)-C(9)-C(8) (19) C(19)-C(18)-H(18) C(10)-C(9)-C(8) (19) C(20)-C(19)-C(18) 120.1(2) C(9)-C(10)-C(5) (18) C(20)-C(19)-H(19) C(9)-C(10)-C(4) (15) C(18)-C(19)-H(19) C(5)-C(10)-C(4) (18) C(21)-C(20)-C(19) 119.4(2) C(12)-C(11)-C(16) (14) C(21)-C(20)-H(20) C(12)-C(11)-C(2) (14) C(19)-C(20)-H(20) C(16)-C(11)-C(2) (13) C(20)-C(21)-C(22) 120.7(2) C(13)-C(12)-C(11) (15) C(20)-C(21)-H(21) C(13)-C(12)-H(12) C(22)-C(21)-H(21) C(11)-C(12)-H(12) C(17)-C(22)-C(21) 120.7(2) C(14)-C(13)-C(12) (15) C(17)-C(22)-H(22) C(14)-C(13)-H(13) C(21)-C(22)-H(22) C(12)-C(13)-H(13) N(3)-C(23)-C(17) (14) O(2)-C(14)-C(13) (15) N(3)-C(23)-H(23A) O(2)-C(14)-C(15) (15) C(17)-C(23)-H(23A) C(13)-C(14)-C(15) (15) N(3)-C(23)-H(23B) C(16)-C(15)-C(14) (15) C(17)-C(23)-H(23B) C(16)-C(15)-H(15) H(23A)-C(23)-H(23B) 107.8
50 Table S4. Anisotropic displacement parameters (Å ) for 3b. The anisotropic displacement factor exponent takes the form: 2 2 [h 2 a* 2 U hka*b*U 12] U 11 U 22 U 33 U 23 U 13 U 12
51 Table S5. Hydrogen coordinates ( 10 4 ) and isotropic displacement parameters (Å ) for 152XYZ14_0m x y z U(eq) H(2A) 1240(30) 3380(30) 1435(9) 134(10) H(1) 6370(20) 7010(20) 1638(6) 82(7) H(2) H(5) H(6) H(7) H(8) H(12) H(13) H(15) H(16) H(18) H(19) H(20) H(21) H(22) H(23A) H(23B) Table S6. Hydrogen bonds for 3b D H A d(d H) / Å d(h A) / Å d(d A) / Å < (DHA) / O(2)-H(2A)...O(1)#1 0.96(3) 1.73(3) (17) 165(3) N(1)-H(1)...O(1)#2 0.88(2) 2.46(2) 3.137(2) 133.7(17) Symmetry transformations used to generate equivalent atoms: #1: x 1, y, z; #2: x + 3/2, y + 1/2, z.
52 Figure S43. ORTEP structure of 3b.
53 Figure S44. Unit cell of the structure 3b.
54 Table S7. Crystal data and structure refinement for 3d Identification code 162XYZ14 (Solved by: Rubén A. Toscano) Project Title E 79 Empirical formula C 21 H 18 N 2 O 3 Formula weight Temperature / K 298(2) Wavelength / Å Crystal system monoclinic Space group C 2/c Unit cell dimensions a = (2) Å = 90 b = (1) Å = (1) c = (4) Å = 90 Volume / Å (9) Z 8 Density (calculated) / (Mg m -3 ) Absorption coefficient / mm F(000) 1456 Crystal size / color / shape mm / orange / prism Theta range for data collection / to Index ranges h k l 32 Reflections collected Independent reflections 4251 [R(int) = ] Completeness to theta = % Measurement device Bruker Smart Apex CCD diffractometer Absorption correction semi-empirical from equivalents Max. and min. transmission and Refinement method full-matrix least-squares on F 2 Data / restraints / parameters 4251 / 229 / 299
55 Goodness-of-fit on F Final R indices [I > 2 (I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole / e.å and Remarks main residue disorder 23%
56 Table S8. Atomic coordinates ( 10 4 ) and equivalent isotropic displacement parameters (Å ) for 3d. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor x y z U(eq) O(1) 9800(1) 10911(1) 3496(1) 37(1) O(2) 6607(1) 6831(1) 3550(1) 44(1) O(3) 5955(1) 8298(1) 1750(1) 42(1) N(1) 8496(1) 7628(1) 3888(1) 34(1) C(2) 7907(1) 8725(1) 3760(1) 30(1) N(3) 8503(1) 9874(1) 3796(1) 31(1) C(4) 9352(1) 9888(1) 3564(1) 28(1) C(5) 10565(1) 8540(2) 3117(1) 38(1) C(6) 10950(1) 7363(2) 3004(1) 46(1) C(7) 10519(1) 6261(2) 3191(1) 49(1) C(8) 9712(1) 6320(1) 3486(1) 41(1) C(9) 9303(1) 7508(1) 3594(1) 31(1) C(10) 9736(1) 8632(1) 3411(1) 30(1) C(11) 7398(1) 8638(1) 3217(1) 28(1) C(12) 6740(1) 7651(1) 3133(1) 31(1) C(13) 6262(1) 7517(1) 2646(1) 33(1) C(14) 6414(1) 8383(1) 2235(1) 31(1) C(15) 7048(1) 9387(1) 2314(1) 33(1) C(16) 7529(1) 9495(1) 2799(1) 31(1) C17a 7821(2) 10856(3) 4592(1) 39(1) C18a 8530(2) 10664(3) 4970(1) 74(1) C19a 8306(3) 10553(3) 5511(1) 96(1) C20a 7385(3) 10622(3) 5661(1) 90(1) C21a 6703(3) 10796(4) 5301(1) 88(1) C22a 6907(2) 10911(3) 4762(1) 64(1) C17Bb 7583(14) 10970(40) 4532(6) 63(2) C18Bb 8063(14) 10580(30) 4984(7) 76(2) C19Bb 7577(17) 10420(30) 5461(6) 86(2) C20Bb 6646(17) 10770(40) 5481(6) 84(2) C21Bb 6168(12) 11060(20) 5035(7) 79(2) C22Bb 6645(13) 11280(20) 4562(6) 68(2) C(23) 8061(1) 11036(1) 4012(1) 37(1)
57 Table S9. Bond lengths and angles for 3d Bond length / Å O(1)-C(4) (16) C(15)-C(16) 1.380(2) O(2)-C(12) (17) C(15)-H(15) O(2)-H(2A) 0.84(2) C(16)-H(16) O(3)-C(14) (18) C17a-C22a 1.372(3) O(3)-H(3) 0.88(2) C17a-C18a 1.378(3) N(1)-C(9) (18) C17a-C(23) 1.507(2) N(1)-C(2) (18) C18a-C19a 1.399(4) N(1)-H(1) 0.828(18) C18a-H18a C(2)-N(3) (17) C19a-C20a 1.365(5) C(2)-C(11) (19) C19a-H19a C(2)-H(2) C20a-C21a 1.316(5) N(3)-C(4) (17) C20a-H20a N(3)-C(23) (17) C21a-C22a 1.389(4) C(4)-C(10) (19) C21a-H21a C(5)-C(6) 1.375(2) C22a-H22a C(5)-C(10) (19) C17Bb-C18Bb 1.366(9) C(5)-H(5) C17Bb-C22Bb 1.370(9) C(6)-C(7) 1.386(2) C17Bb-C(23) 1.480(8) C(6)-H(6) C18Bb-C19Bb 1.400(9) C(7)-C(8) 1.375(2) C18Bb-H18Bb C(7)-H(7) C19Bb-C20Bb 1.368(10) C(8)-C(9) 1.396(2) C19Bb-H19Bb C(8)-H(8) C20Bb-C21Bb 1.325(10) C(9)-C(10) (19) C20Bb-H20Bb C(11)-C(16) (19) C21Bb-C22Bb 1.393(9) C(11)-C(12) (18) C21Bb-H21Bb C(12)-C(13) 1.386(2) C22Bb-H22Bb C(13)-C(14) 1.386(2) C(23)-H(23A) C(13)-H(13) C(23)-H(23B) C(14)-C(15) (19) Bond angle / C(12)-O(2)-H(2A) 111.1(15) C(9)-N(1)-H(1) 117.4(12) C(14)-O(3)-H(3) 109.4(14) C(2)-N(1)-H(1) 112.8(12)
58 C(9)-N(1)-C(2) (11) N(1)-C(2)-N(3) (11) N(1)-C(2)-C(11) (11) C(12)-C(13)-H(13) N(3)-C(2)-C(11) (11) C(14)-C(13)-H(13) N(1)-C(2)-H(2) O(3)-C(14)-C(13) (13) N(3)-C(2)-H(2) O(3)-C(14)-C(15) (13) C(11)-C(2)-H(2) C(13)-C(14)-C(15) (13) C(4)-N(3)-C(2) (11) C(16)-C(15)-C(14) (13) C(4)-N(3)-C(23) (11) C(16)-C(15)-H(15) C(2)-N(3)-C(23) (11) C(14)-C(15)-H(15) O(1)-C(4)-N(3) (12) C(15)-C(16)-C(11) (13) O(1)-C(4)-C(10) (12) C(15)-C(16)-H(16) N(3)-C(4)-C(10) (11) C(11)-C(16)-H(16) C(6)-C(5)-C(10) (14) C22a-C17a-C18a 118.0(2) C(6)-C(5)-H(5) C22a-C17a-C(23) 121.9(2) C(10)-C(5)-H(5) C18a-C17a-C(23) 120.1(2) C(5)-C(6)-C(7) (15) C17a-C18a-C19a 119.8(3) C(5)-C(6)-H(6) C17a-C18a-H18a C(7)-C(6)-H(6) C19a-C18a-H18a C(8)-C(7)-C(6) (15) C20a-C19a-C18a 119.9(3) C(8)-C(7)-H(7) C20a-C19a-H19a C(6)-C(7)-H(7) C18a-C19a-H19a C(7)-C(8)-C(9) (14) C21a-C20a-C19a 120.7(3) C(7)-C(8)-H(8) C21a-C20a-H20a C(9)-C(8)-H(8) C19a-C20a-H20a N(1)-C(9)-C(8) (13) C20a-C21a-C22a 120.6(3) N(1)-C(9)-C(10) (12) C20a-C21a-H21a C(8)-C(9)-C(10) (13) C22a-C21a-H21a C(5)-C(10)-C(9) (13) C17a-C22a-C21a 121.0(3) C(5)-C(10)-C(4) (12) C17a-C22a-H22a C(9)-C(10)-C(4) (12) C21a-C22a-H22a C(16)-C(11)-C(12) (13) C18Bb-C17Bb-C22Bb 119.3(7) C(16)-C(11)-C(2) (12) C18Bb-C17Bb-C(23) 120.7(12) C(12)-C(11)-C(2) (12) C22Bb-C17Bb-C(23) 119.9(12) O(2)-C(12)-C(13) (12) C17Bb-C18Bb-C19Bb 119.6(8) O(2)-C(12)-C(11) (13) C17Bb-C18Bb-H18Bb C(13)-C(12)-C(11) (13) C19Bb-C18Bb-H18Bb 120.2
59 C(12)-C(13)-C(14) (13) C20Bb-C19Bb-C18Bb 119.5(8) C20Bb-C19Bb-H19Bb C21Bb-C22Bb-H22Bb C18Bb-C19Bb-H19Bb N(3)-C(23)-C17Bb 119.2(14) C21Bb-C20Bb-C19Bb 120.1(8) N(3)-C(23)-C17a (14) C21Bb-C20Bb-H20Bb N(3)-C(23)-H(23A) C19Bb-C20Bb-H20Bb C17Bb-C(23)-H(23A) 95.1 C20Bb-C21Bb-C22Bb 120.2(9) C17a-C(23)-H(23A) C20Bb-C21Bb-H21Bb N(3)-C(23)-H(23B) C22Bb-C21Bb-H21Bb C17Bb-C(23)-H(23B) C17Bb-C22Bb-C21Bb 119.7(8) C17a-C(23)-H(23B) C17Bb-C22Bb-H22Bb H(23A)-C(23)-H(23B) 108.1
60 Table S10. Anisotropic displacement parameters (Å ) for 3d. The anisotropic displacement factor exponent takes the form: -2 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 O(1) 31(1) 27(1) 53(1) 4(1) 2(1) 6(1) O(2) 36(1) 45(1) 51(1) 18(1) 5(1) 17(1) O(3) 53(1) 35(1) 38(1) 2(1) 3(1) 6(1) N(1) 30(1) 29(1) 43(1) 8(1) 4(1) 5(1) C(2) 26(1) 29(1) 34(1) 0(1) 8(1) 4(1) N(3) 30(1) 26(1) 36(1) 4(1) 6(1) 3(1) C(4) 26(1) 29(1) 31(1) 2(1) 1(1) 4(1) C(5) 30(1) 37(1) 46(1) 2(1) 6(1) 3(1) C(6) 33(1) 47(1) 58(1) 4(1) 11(1) 6(1) C(7) 42(1) 37(1) 67(1) 6(1) 3(1) 10(1) C(8) 38(1) 28(1) 56(1) 3(1) 1(1) 0(1) C(9) 28(1) 30(1) 34(1) 2(1) 2(1) 2(1) C(10) 26(1) 29(1) 34(1) 1(1) 1(1) 2(1) C(11) 22(1) 26(1) 36(1) 1(1) 6(1) 0(1) C(12) 25(1) 27(1) 41(1) 5(1) 5(1) 2(1) C(13) 28(1) 26(1) 44(1) 0(1) 3(1) 4(1) C(14) 30(1) 28(1) 34(1) 4(1) 4(1) 3(1) C(15) 36(1) 28(1) 35(1) 2(1) 9(1) 2(1) C(16) 28(1) 26(1) 40(1) 2(1) 8(1) 4(1) C17a 57(1) 27(1) 34(1) 2(1) 10(1) 4(1) C18a 83(2) 89(2) 49(1) 3(1) 7(1) 19(2) C19a 140(3) 99(2) 49(1) 14(1) 14(2) 18(2) C20a 160(3) 60(2) 52(2) 2(1) 38(2) 11(2) C21a 115(2) 75(2) 75(2) 3(2) 54(2) 1(2) C22a 69(1) 62(2) 63(2) 5(1) 27(1) 1(1) C17Bb 79(4) 57(5) 53(4) 0(4) 16(4) 2(5) C18Bb 105(4) 69(4) 54(4) 6(4) 15(3) 8(4) C19Bb 123(4) 79(4) 57(4) 4(4) 22(4) 11(4) C20Bb 119(4) 68(5) 65(4) 1(5) 32(4) 2(5) C21Bb 98(4) 72(5) 68(5) 0(5) 37(4) 0(5) C22Bb 82(4) 60(5) 63(4) 3(4) 31(4) 1(4) C(23) 44(1) 32(1) 36(1) 2(1) 6(1) 4(1)
61 Table S11. Hydrogen coordinates ( 10 4 ) and isotropic displacement parameters (Å ) for 3d x y z U(eq) H(2A) 6081(16) 6460(20) 3521(8) 67 H(3) 5676(15) 7550(20) 1722(8) 63 H(1) 8185(12) 6968(17) 3942(7) 41 H(2) H(5) H(6) H(7) H(8) H(13) H(15) H(16) H18a H19a H20a H21a H22a H18Bb H19Bb H20Bb H21Bb H22Bb H(23A) H(23B) Table S12. Hydrogen bonds for 3d D H A d(d H) / Å d(h A) / Å d(d A) / Å < (DHA) / O(2)-H(2A)...O(1)#1 0.84(2) 1.90(2) (14) 169(2) O(3)-H(3)...O(1)#2 0.88(2) 1.91(2) (15) 167(2) N(1)-H(1)...O(2) 0.828(18) 2.422(17) (17) 118.1(14) Symmetry transformations used to generate equivalent atoms: #1: x 1/2, y 1/2, z; #2: x + 3/2, y 1/2, z + 1/2.
62 Figure S45. ORTEP structure of 3d.
63 Figure S46. Unit cell of the structure 3d.
64 Table S13. Crystal data and structure refinement for 3f Identification code 166XYZ14 (Solved by: Rubén A. Toscano) Project Title E 81 Empirical formula C 23 H 23 N 3 O Formula weight Temperature / K 298(2) Wavelength / Å Crystal system monoclinic Space group P 21/c Unit cell dimensions a = (8) Å = 90 b = (8) Å = (15) c = (7) Å = 90 Volume / Å (2) Z 4 Density (calculated) / (Mg m -3 ) Absorption coefficient / mm F(000) 760 Crystal size / color / shape mm / colorless / block Theta range for data collection / to Index ranges h k l Reflections collected Independent reflections 4369 [R(int) = ] Completeness to theta = % Measurement device Bruker Smart Apex CCD diffractometer Absorption correction semi-empirical from equivalents Max. and min. transmission and Refinement method full-matrix least-squares on F 2 Data / restraints / parameters 4369 / 0 / 250
65 Goodness-of-fit on F Final R indices [I > 2 (I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Extinction coefficient (18) Largest diff. peak and hole / e.å and
66 Table S14. Atomic coordinates ( 10 4 ) and equivalent isotropic displacement parameters (Å ) for 3f. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor x y z U(eq) O(1) 4909(1) 6329(1) 2278(1) 71(1) N(1) 4715(1) 9204(1) 2612(2) 56(1) N(2) 1059(1) 10899(1) -944(2) 74(1) C(2) 4465(1) 8802(1) 1401(2) 51(1) N(3) 4268(1) 7751(1) 1562(1) 53(1) C(4) 4932(2) 7220(1) 2312(2) 54(1) C(5) 6352(2) 7277(1) 3960(2) 69(1) C(6) 6942(2) 7761(2) 4844(2) 81(1) C(7) 6808(2) 8750(2) 4982(2) 78(1) C(8) 6089(2) 9243(1) 4235(2) 65(1) C(9) 5489(1) 8751(1) 3335(2) 50(1) C(10) 5622(1) 7756(1) 3195(2) 54(1) C(11) 3547(1) 9332(1) 796(2) 49(1) C(12) 2690(2) 9631(1) 1445(2) 56(1) C(13) 1877(2) 10148(1) 887(2) 61(1) C(14) 1884(2) 10392(1) -372(2) 56(1) C(15) 2744(2) 10084(1) -1014(2) 57(1) C(16) 3552(2) 9574(1) -439(2) 54(1) C(17) 307(2) 11384(2) -190(3) 88(1) C(18) 1146(2) 11244(2) -2193(2) 96(1) C(19) 2601(2) 6907(1) 906(2) 55(1) C(20) 2204(2) 7049(2) 2047(2) 68(1) C(21) 1215(2) 6725(2) 2318(3) 93(1) C(22) 603(2) 6259(2) 1464(4) 110(1) C(23) 962(3) 6107(2) 323(4) 114(1) C(24) 1966(2) 6421(2) 36(2) 91(1) C(25) 3677(2) 7240(1) 578(2) 61(1)
67 Table S15. Bond lengths and angles for 3f Bond length / Å O(1)-C(4) 1.237(2) C(13)-C(14) 1.406(3) N(1)-C(9) 1.381(2) C(13)-H(13) N(1)-C(2) 1.448(2) C(14)-C(15) 1.389(3) N(1)-H(1) 0.84(2) C(15)-C(16) 1.374(3) N(2)-C(14) 1.386(3) C(15)-H(15) N(2)-C(18) 1.444(3) C(16)-H(16) N(2)-C(17) 1.451(3) C(17)-H(17A) C(2)-N(3) 1.492(2) C(17)-H(17B) C(2)-C(11) 1.505(2) C(17)-H(17C) C(2)-H(2) C(18)-H(18A) N(3)-C(4) 1.362(2) C(18)-H(18B) N(3)-C(25) 1.460(2) C(18)-H(18C) C(4)-C(10) 1.472(3) C(19)-C(20) 1.371(3) C(5)-C(6) 1.366(3) C(19)-C(24) 1.389(3) C(5)-C(10) 1.387(3) C(19)-C(25) 1.502(3) C(5)-H(5) C(20)-C(21) 1.380(3) C(6)-C(7) 1.393(3) C(20)-H(20) C(6)-H(6) C(21)-C(22) 1.347(4) C(7)-C(8) 1.376(3) C(21)-H(21) C(7)-H(7) C(22)-C(23) 1.353(4) C(8)-C(9) 1.389(3) C(22)-H(22) C(8)-H(8) C(23)-C(24) 1.397(4) C(9)-C(10) 1.401(2) C(23)-H(23) C(11)-C(16) 1.379(2) C(24)-H(24) C(11)-C(12) 1.388(2) C(25)-H(25A) C(12)-C(13) 1.375(3) C(25)-H(25B) C(12)-H(12) Bond angle / C(9)-N(1)-C(2) (14) N(1)-C(2)-N(3) (13) C(9)-N(1)-H(1) 115.7(14) N(1)-C(2)-C(11) (14) C(2)-N(1)-H(1) 112.7(14) N(3)-C(2)-C(11) (14) C(14)-N(2)-C(18) 119.9(2) N(1)-C(2)-H(2) C(14)-N(2)-C(17) (19) N(3)-C(2)-H(2) C(18)-N(2)-C(17) 117.0(2) C(11)-C(2)-H(2) 108.6
68 C(4)-N(3)-C(25) (14) C(16)-C(15)-C(14) (17) C(4)-N(3)-C(2) (14) C(16)-C(15)-H(15) C(25)-N(3)-C(2) (14) C(14)-C(15)-H(15) O(1)-C(4)-N(3) (18) C(15)-C(16)-C(11) (17) O(1)-C(4)-C(10) (17) C(15)-C(16)-H(16) N(3)-C(4)-C(10) (14) C(11)-C(16)-H(16) C(6)-C(5)-C(10) (18) N(2)-C(17)-H(17A) C(6)-C(5)-H(5) N(2)-C(17)-H(17B) C(10)-C(5)-H(5) H(17A)-C(17)-H(17B) C(5)-C(6)-C(7) 119.7(2) N(2)-C(17)-H(17C) C(5)-C(6)-H(6) H(17A)-C(17)-H(17C) C(7)-C(6)-H(6) H(17B)-C(17)-H(17C) C(8)-C(7)-C(6) 120.5(2) N(2)-C(18)-H(18A) C(8)-C(7)-H(7) N(2)-C(18)-H(18B) C(6)-C(7)-H(7) H(18A)-C(18)-H(18B) C(7)-C(8)-C(9) (18) N(2)-C(18)-H(18C) C(7)-C(8)-H(8) H(18A)-C(18)-H(18C) C(9)-C(8)-H(8) H(18B)-C(18)-H(18C) N(1)-C(9)-C(8) (15) C(20)-C(19)-C(24) 117.1(2) N(1)-C(9)-C(10) (16) C(20)-C(19)-C(25) (17) C(8)-C(9)-C(10) (16) C(24)-C(19)-C(25) (19) C(5)-C(10)-C(9) (18) C(19)-C(20)-C(21) 121.4(2) C(5)-C(10)-C(4) (16) C(19)-C(20)-H(20) C(9)-C(10)-C(4) (16) C(21)-C(20)-H(20) C(16)-C(11)-C(12) (17) C(22)-C(21)-C(20) 120.9(3) C(16)-C(11)-C(2) (16) C(22)-C(21)-H(21) C(12)-C(11)-C(2) (16) C(20)-C(21)-H(21) C(13)-C(12)-C(11) (17) C(21)-C(22)-C(23) 119.6(3) C(13)-C(12)-H(12) C(21)-C(22)-H(22) C(11)-C(12)-H(12) C(23)-C(22)-H(22) C(12)-C(13)-C(14) (18) C(22)-C(23)-C(24) 120.3(3) C(12)-C(13)-H(13) C(22)-C(23)-H(23) C(14)-C(13)-H(13) C(24)-C(23)-H(23) N(2)-C(14)-C(15) (18) C(19)-C(24)-C(23) 120.6(3)
69 N(2)-C(14)-C(13) (18) C(19)-C(24)-H(24) C(15)-C(14)-C(13) (18) C(23)-C(24)-H(24) N(3)-C(25)-C(19) (14) N(3)-C(25)-H(25B) N(3)-C(25)-H(25A) C(19)-C(25)-H(25B) C(19)-C(25)-H(25A) H(25A)-C(25)-H(25B) N(3)-C(25)-C(19) (14) N(3)-C(25)-H(25B) N(3)-C(25)-H(25A) C(19)-C(25)-H(25B) 108.5
70 Table S16. Anisotropic displacement parameters (Å ) for 3f. The anisotropic displacement factor exponent takes the form: -2 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 O(1) 94(1) 26(1) 93(1) 4(1) 22(1) 0(1) N(1) 70(1) 24(1) 72(1) 0(1) 1(1) 3(1) N(2) 70(1) 70(1) 82(1) 7(1) 7(1) 3(1) C(2) 59(1) 29(1) 67(1) 3(1) 12(1) 4(1) N(3) 66(1) 28(1) 65(1) 0(1) 13(1) 5(1) C(4) 66(1) 28(1) 70(1) 6(1) 23(1) 1(1) C(5) 72(1) 39(1) 95(2) 11(1) 9(1) 11(1) C(6) 80(2) 60(1) 102(2) 17(1) 10(1) 16(1) C(7) 82(2) 63(1) 87(2) 2(1) 12(1) 4(1) C(8) 73(1) 40(1) 81(1) 1(1) 1(1) 6(1) C(9) 54(1) 33(1) 64(1) 5(1) 10(1) 2(1) C(10) 57(1) 33(1) 72(1) 7(1) 16(1) 3(1) C(11) 57(1) 30(1) 62(1) 1(1) 8(1) 6(1) C(12) 64(1) 49(1) 57(1) 7(1) 13(1) 1(1) C(13) 58(1) 58(1) 69(1) 2(1) 14(1) 1(1) C(14) 57(1) 43(1) 66(1) 2(1) 2(1) 8(1) C(15) 68(1) 50(1) 53(1) 2(1) 6(1) 11(1) C(16) 63(1) 41(1) 60(1) 2(1) 14(1) 6(1) C(17) 64(1) 76(2) 122(2) 9(1) 2(1) 12(1) C(18) 120(2) 86(2) 79(2) 6(1) 29(2) 8(2) C(19) 79(1) 32(1) 55(1) 5(1) 4(1) 6(1) C(20) 66(1) 71(1) 66(1) 5(1) 1(1) 8(1) C(21) 72(2) 97(2) 110(2) 23(2) 11(2) 6(1) C(22) 78(2) 89(2) 161(3) 37(2) 15(2) 20(2) C(23) 119(3) 78(2) 139(3) 8(2) 53(2) 39(2) C(24) 133(2) 63(1) 75(2) 5(1) 17(2) 22(2) C(25) 97(2) 33(1) 54(1) 3(1) 18(1) 9(1)
71 Table S17. Hydrogen coordinates ( 10 4 ) and isotropic displacement parameters (Å ) for 3f x y z U(eq) H(1) 4737(15) 9808(16) 2608(18) 67 H(2) H(5) H(6) H(7) H(8) H(12) H(13) H(15) H(16) H(17A) H(17B) H(17C) H(18A) H(18B) H(18C) H(20) H(21) H(22) H(23) H(24) H(25A) H(25B) Table S18. Hydrogen bonds for 3f D H A d(d H) / Å d(h A) / Å d(d A) / Å < (DHA) / N(1)-H(1)...O(1)#1 0.84(2) 2.16(2) (18) 169.4(18) Symmetry transformations used to generate equivalent atoms: #1: x + 1, y + 1/2, z + 1/2.
72 Figure S47. ORTEP structure of 3f.
73 Figure S48. Unit cell of the structure 3f.
74 Table S19. Crystal data and structure refinement for 3i Identification code 174XYZ14 (Solved by: Rubén A. Toscano) Project Title E 84 Empirical formula C 23 H 22 N 2 O 3 Formula weight Temperature / K 298(2) Wavelength / Å Crystal system triclinic Space group P -1 Unit cell dimensions a = 9.651(6) Å (12) b = (6) Å (13) c = (12) Å = (12) Volume / Å (19) Z 4 Density (calculated) / (Mg m -3 ) Absorption coefficient / mm F(000) 792 Crystal size / color / shape mm / colorless / block Theta range for data collection / to Index ranges h k l Reflections collected Independent reflections 8566 [R(int) = ] Completeness to theta = % Measurement device Bruker Smart Apex CCD diffractometer Absorption correction semi-empirical from equivalents Max. and min. transmission and Refinement method full-matrix least-squares on F 2 Data / restraints / parameters 8566 / 242 / 571 Goodness-of-fit on F
75 Final R indices [I>2 (I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Extinction coefficient (13) Largest diff. peak and hole / e.å and Remarks Crystal twinned /0.4222, Main residue disorder 11%
76 Table S20. Atomic coordinates ( 10 4 ) and equivalent isotropic displacement parameters (Å ) for 3i. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor x y z U(eq) O(1) 2950(1) 7948(1) 4035(1) 69(1) O(2) 3034(1) 8103(1) 4988(1) 56(1) O(3) 5566(1) 5111(1) 3567(1) 69(1) N(1) 112(2) 9654(1) 4305(1) 48(1) C(2) 324(2) 8244(2) 4638(1) 41(1) N(3) 953(1) 7861(1) 4610(1) 43(1) C(4) 1979(2) 8396(2) 4072(1) 45(1) C(5) 2854(2) 10145(2) 2972(1) 60(1) C(6) 2870(2) 11297(2) 2518(1) 76(1) C(7) 1937(2) 11886(2) 2651(1) 76(1) C(8) 992(2) 11353(2) 3230(1) 61(1) C(9) 965(2) 10181(2) 3694(1) 44(1) C(10) 1902(2) 9571(2) 3563(1) 44(1) C(11) 1710(2) 7373(1) 4356(1) 38(1) C(12) 3098(2) 7343(1) 4546(1) 40(1) C(13) 4413(2) 6606(2) 4294(1) 46(1) C(14) 4338(2) 5873(2) 3848(1) 49(1) C(15) 2991(2) 5868(2) 3661(1) 55(1) C(16) 1697(2) 6613(2) 3914(1) 48(1) C(17) 1659(2) 7289(2) 5813(1) 42(1) C(18) 2639(2) 8583(2) 5761(1) 51(1) C(19) 3274(2) 8980(2) 6333(1) 63(1) C(20) 2941(2) 8100(2) 6969(1) 67(1) C(21) 1948(2) 6824(2) 7037(1) 70(1) C(22) 1299(2) 6421(2) 6461(1) 59(1) C(23) 1041(2) 6804(2) 5187(1) 49(1) C(24) 4386(2) 7959(2) 5310(1) 62(1) C(25) 7000(2) 5009(2) 3769(1) 77(1) O(4) 9954(1) 7689(2) 878(1) 96(1) O(5) 3585(1) 8004(1) 12(1) 60(1) O(6) 3758(2) 5018(1) 1315(1) 76(1)
77 N(31) 5599(2) 9409(1) 622(1) 54(1) C(32) 6309(2) 8007(2) 270(1) 49(1) N(33) 7920(2) 7628(2) 293(1) 56(1) C(34) 8588(2) 8125(2) 845(1) 61(1) C(35) 8142(2) 9741(2) 1999(1) 68(1) C(36) 7211(3) 10801(2) 2495(1) 79(1) C(37) 5728(3) 11361(2) 2382(1) 79(1) C(38) 5155(2) 10902(2) 1777(1) 66(1) C(39) 6084(2) 9844(2) 1267(1) 49(1) C(40) 7586(2) 9234(2) 1382(1) 52(1) C(41) 5737(2) 7132(2) 551(1) 43(1) C(42) 4298(2) 7180(2) 400(1) 44(1) C(43) 3668(2) 6466(2) 659(1) 51(1) C(44) 4492(2) 5679(2) 1077(1) 53(1) C(45) 5914(2) 5603(2) 1238(1) 57(1) C(46) 6525(2) 6336(2) 966(1) 53(1) C47a 8947(15) 7182(6) 878(2) 52(1) C48a 8650(7) 8524(4) 787(2) 54(1) C49a 8930(6) 9003(4) 1313(2) 62(1) C50a 9477(5) 8149(4) 1947(2) 74(1) C51a 9749(7) 6829(4) 2052(2) 94(1) C52a 9514(7) 6341(4) 1517(2) 83(1) C47Bb 8930(40) 6986(14) 928(4) 64(2) C48Bb 8919(16) 8221(11) 907(4) 67(2) C49Bb 9048(15) 8572(11) 1508(5) 83(2) C50Bb 9131(13) 7677(12) 2125(4) 97(2) C51Bb 9068(12) 6485(10) 2154(4) 98(2) C52Bb 8961(11) 6111(9) 1554(4) 84(2) C(53) 8800(2) 6596(2) 291(1) 65(1) C(54) 2168(2) 8031(2) 253(1) 68(1) C(55) 4502(3) 4253(3) 1777(1) 108(1)
78 Table S21. Bond lengths and angles for 3i Bond length / Å O(1)-C(4) (18) C(17)-C(18) 1.380(2) O(2)-C(12) (19) C(17)-C(23) 1.509(2) O(2)-C(24) 1.422(2) C(18)-C(19) 1.374(2) O(3)-C(14) (19) C(18)-H(18) O(3)-C(25) 1.416(2) C(19)-C(20) 1.366(3) N(1)-C(9) 1.377(2) C(19)-H(19) N(1)-C(2) 1.448(2) C(20)-C(21) 1.364(3) N(1)-H(1) 0.831(13) C(20)-H(20) C(2)-N(3) (19) C(21)-C(22) 1.389(3) C(2)-C(11) 1.515(2) C(21)-H(21) C(2)-H(2) C(22)-H(22) N(3)-C(4) 1.357(2) C(23)-H(23A) N(3)-C(23) 1.452(2) C(23)-H(23B) C(4)-C(10) 1.467(2) C(24)-H(24A) C(5)-C(6) 1.369(3) C(24)-H(24B) C(5)-C(10) 1.396(2) C(24)-H(24C) C(5)-H(5) C(25)-H(25A) C(6)-C(7) 1.369(3) C(25)-H(25B) C(6)-H(6) C(25)-H(25C) C(7)-C(8) 1.373(3) O(4)-C(34) 1.227(2) C(7)-H(7) O(5)-C(42) (19) C(8)-C(9) 1.392(2) O(5)-C(54) 1.421(2) C(8)-H(8) O(6)-C(44) 1.374(2) C(9)-C(10) 1.391(2) O(6)-C(55) 1.412(3) C(11)-C(16) 1.384(2) N(31)-C(39) 1.387(2) C(11)-C(12) 1.396(2) N(31)-C(32) 1.449(2) C(12)-C(13) 1.384(2) N(31)-H(31) 0.844(14) C(13)-C(14) 1.382(2) C(32)-N(33) 1.451(2) C(13)-H(13) C(32)-C(41) 1.518(2) C(14)-C(15) 1.374(2) C(32)-H(32) C(15)-C(16) 1.374(2) N(33)-C(34) 1.356(2) C(15)-H(15) N(33)-C(53) 1.449(2) C(16)-H(16) C(34)-C(40) 1.468(3) C(17)-C(22) 1.379(2) C(35)-C(36) 1.375(3)
79 C(35)-C(40) 1.396(2) C50a-C51a 1.359(5) C(35)-H(35) C50a-H50a C(36)-C(37) 1.365(3) C51a-C52a 1.389(4) C(36)-H(36) C51a-H51a C(37)-C(38) 1.368(3) C52a-H52a C(37)-H(37) C47Bb-C48Bb 1.366(6) C(38)-C(39) 1.389(3) C47Bb-C52Bb 1.375(7) C(38)-H(38) C47Bb-C(53) 1.482(6) C(39)-C(40) 1.389(2) C48Bb-C49Bb 1.390(6) C(41)-C(46) 1.373(2) C48Bb-H48Bb C(41)-C(42) 1.390(2) C49Bb-C50Bb 1.363(7) C(42)-C(43) 1.375(2) C49Bb-H49Bb C(43)-C(44) 1.381(2) C50Bb-C51Bb 1.344(7) C(43)-H(43) C50Bb-H50Bb C(44)-C(45) 1.370(3) C51Bb-C52Bb 1.396(6) C(45)-C(46) 1.394(2) C51Bb-H51Bb C(45)-H(45) C52Bb-H52Bb C(46)-H(46) C(53)-H(53A) C47a-C52a 1.377(5) C(53)-H(53B) C47a-C48a 1.382(4) C(54)-H(54A) C47a-C(53) 1.528(4) C(54)-H(54B) C48a-C49a 1.383(4) C(54)-H(54C) C48a-H48a C(55)-H(55A) C49a-C50a 1.370(4) C(55)-H(55B) C49a-H49a C(55)-H(55C) Bond angle / C(12)-O(2)-C(24) (12) C(11)-C(2)-H(2) C(14)-O(3)-C(25) (15) C(4)-N(3)-C(23) (13) C(9)-N(1)-C(2) (13) C(4)-N(3)-C(2) (13) C(9)-N(1)-H(1) 118.2(12) C(23)-N(3)-C(2) (12) C(2)-N(1)-H(1) 111.7(12) O(1)-C(4)-N(3) (15) N(1)-C(2)-N(3) (12) O(1)-C(4)-C(10) (14) N(1)-C(2)-C(11) (12) N(3)-C(4)-C(10) (13) N(3)-C(2)-C(11) (12) C(6)-C(5)-C(10) (18) N(1)-C(2)-H(2) C(6)-C(5)-H(5) 119.6
80 N(3)-C(2)-H(2) C(10)-C(5)-H(5) C(7)-C(6)-C(5) (19) C(19)-C(18)-C(17) (16) C(7)-C(6)-H(6) C(19)-C(18)-H(18) C(5)-C(6)-H(6) C(17)-C(18)-H(18) C(6)-C(7)-C(8) (19) C(20)-C(19)-C(18) (17) C(6)-C(7)-H(7) C(20)-C(19)-H(19) C(8)-C(7)-H(7) C(18)-C(19)-H(19) C(7)-C(8)-C(9) (18) C(21)-C(20)-C(19) (18) C(7)-C(8)-H(8) C(21)-C(20)-H(20) C(9)-C(8)-H(8) C(19)-C(20)-H(20) N(1)-C(9)-C(10) (14) C(20)-C(21)-C(22) (18) N(1)-C(9)-C(8) (16) C(20)-C(21)-H(21) C(10)-C(9)-C(8) (16) C(22)-C(21)-H(21) C(9)-C(10)-C(5) (16) C(17)-C(22)-C(21) (17) C(9)-C(10)-C(4) (14) C(17)-C(22)-H(22) C(5)-C(10)-C(4) (15) C(21)-C(22)-H(22) C(16)-C(11)-C(12) (13) N(3)-C(23)-C(17) (13) C(16)-C(11)-C(2) (13) N(3)-C(23)-H(23A) C(12)-C(11)-C(2) (13) C(17)-C(23)-H(23A) O(2)-C(12)-C(13) (14) N(3)-C(23)-H(23B) O(2)-C(12)-C(11) (13) C(17)-C(23)-H(23B) C(13)-C(12)-C(11) (14) H(23A)-C(23)-H(23B) C(14)-C(13)-C(12) (14) O(2)-C(24)-H(24A) C(14)-C(13)-H(13) O(2)-C(24)-H(24B) C(12)-C(13)-H(13) H(24A)-C(24)-H(24B) O(3)-C(14)-C(15) (15) O(2)-C(24)-H(24C) O(3)-C(14)-C(13) (15) H(24A)-C(24)-H(24C) C(15)-C(14)-C(13) (14) H(24B)-C(24)-H(24C) C(16)-C(15)-C(14) (16) O(3)-C(25)-H(25A) C(16)-C(15)-H(15) O(3)-C(25)-H(25B) C(14)-C(15)-H(15) H(25A)-C(25)-H(25B) C(15)-C(16)-C(11) (15) O(3)-C(25)-H(25C) C(15)-C(16)-H(16) H(25A)-C(25)-H(25C) C(11)-C(16)-H(16) H(25B)-C(25)-H(25C) 109.5
81 C(22)-C(17)-C(18) (15) C(42)-O(5)-C(54) (13) C(22)-C(17)-C(23) (15) C(44)-O(6)-C(55) (17) C(18)-C(17)-C(23) (14) C(39)-N(31)-C(32) (14) C(39)-N(31)-H(31) 114.4(13) O(5)-C(42)-C(41) (13) C(32)-N(31)-H(31) 114.0(12) C(43)-C(42)-C(41) (15) N(31)-C(32)-N(33) (13) C(42)-C(43)-C(44) (16) N(31)-C(32)-C(41) (14) C(42)-C(43)-H(43) N(33)-C(32)-C(41) (13) C(44)-C(43)-H(43) N(31)-C(32)-H(32) C(45)-C(44)-O(6) (16) N(33)-C(32)-H(32) C(45)-C(44)-C(43) (15) C(41)-C(32)-H(32) O(6)-C(44)-C(43) (16) C(34)-N(33)-C(53) (15) C(44)-C(45)-C(46) (16) C(34)-N(33)-C(32) (14) C(44)-C(45)-H(45) C(53)-N(33)-C(32) (14) C(46)-C(45)-H(45) O(4)-C(34)-N(33) (18) C(41)-C(46)-C(45) (16) O(4)-C(34)-C(40) (17) C(41)-C(46)-H(46) N(33)-C(34)-C(40) (15) C(45)-C(46)-H(46) C(36)-C(35)-C(40) (19) C52a-C47a-C48a 117.4(3) C(36)-C(35)-H(35) C52a-C47a-C(53) 119.5(4) C(40)-C(35)-H(35) C48a-C47a-C(53) 122.9(4) C(37)-C(36)-C(35) (19) C47a-C48a-C49a 121.4(3) C(37)-C(36)-H(36) C47a-C48a-H48a C(35)-C(36)-H(36) C49a-C48a-H48a C(36)-C(37)-C(38) 121.1(2) C50a-C49a-C48a 120.1(3) C(36)-C(37)-H(37) C50a-C49a-H49a C(38)-C(37)-H(37) C48a-C49a-H49a C(37)-C(38)-C(39) (19) C51a-C50a-C49a 119.5(3) C(37)-C(38)-H(38) C51a-C50a-H50a C(39)-C(38)-H(38) C49a-C50a-H50a N(31)-C(39)-C(38) (16) C50a-C51a-C52a 120.4(3) N(31)-C(39)-C(40) (16) C50a-C51a-H51a C(38)-C(39)-C(40) (16) C52a-C51a-H51a C(39)-C(40)-C(35) (18) C47a-C52a-C51a 121.1(3) C(39)-C(40)-C(34) (15) C47a-C52a-H52a C(35)-C(40)-C(34) (17) C51a-C52a-H52a 119.4
82 C(46)-C(41)-C(42) (14) C48Bb-C47Bb-C52Bb 119.6(5) C(46)-C(41)-C(32) (14) C48Bb-C47Bb-C(53) 121.6(7) C(42)-C(41)-C(32) (14) C52Bb-C47Bb-C(53) 118.7(8) O(5)-C(42)-C(43) (15) C47Bb-C48Bb-C49Bb 121.0(5) C47Bb-C48Bb-H48Bb C47a-C(53)-H(53A) C49Bb-C48Bb-H48Bb N(33)-C(53)-H(53B) C50Bb-C49Bb-C48Bb 118.7(5) C47Bb-C(53)-H(53B) C50Bb-C49Bb-H49Bb C47a-C(53)-H(53B) C48Bb-C49Bb-H49Bb H(53A)-C(53)-H(53B) C51Bb-C50Bb-C49Bb 120.9(5) O(5)-C(54)-H(54A) C51Bb-C50Bb-H50Bb O(5)-C(54)-H(54B) C49Bb-C50Bb-H50Bb H(54A)-C(54)-H(54B) C50Bb-C51Bb-C52Bb 121.0(5) O(5)-C(54)-H(54C) C50Bb-C51Bb-H51Bb H(54A)-C(54)-H(54C) C52Bb-C51Bb-H51Bb H(54B)-C(54)-H(54C) C47Bb-C52Bb-C51Bb 118.7(5) O(6)-C(55)-H(55A) C47Bb-C52Bb-H52Bb O(6)-C(55)-H(55B) C51Bb-C52Bb-H52Bb H(55A)-C(55)-H(55B) N(33)-C(53)-C47Bb 117.9(7) O(6)-C(55)-H(55C) N(33)-C(53)-C47a 111.3(3) H(55A)-C(55)-H(55C) N(33)-C(53)-H(53A) H(55B)-C(55)-H(55C) C47Bb-C(53)-H(53A) 101.6
83 Table S22. Anisotropic displacement parameters (Å ) for 3i. The anisotropic displacement factor exponent takes the form: 2 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 O(1) 57(1) 87(1) 76(1) 13(1) 6(1) 46(1) O(2) 43(1) 66(1) 67(1) 32(1) 2(1) 22(1) O(3) 48(1) 75(1) 90(1) 40(1) 18(1) 17(1) N(1) 44(1) 49(1) 57(1) 19(1) 1(1) 21(1) C(2) 38(1) 52(1) 39(1) 14(1) 1(1) 21(1) N(3) 38(1) 53(1) 40(1) 10(1) 3(1) 22(1) C(4) 36(1) 58(1) 46(1) 19(1) 4(1) 21(1) C(5) 52(1) 75(1) 51(1) 17(1) 3(1) 21(1) C(6) 70(1) 81(2) 52(1) 1(1) 7(1) 13(1) C(7) 71(1) 61(1) 72(1) 5(1) 7(1) 14(1) C(8) 57(1) 50(1) 73(1) 12(1) 10(1) 19(1) C(9) 38(1) 45(1) 46(1) 16(1) 9(1) 12(1) C(10) 38(1) 55(1) 41(1) 16(1) 5(1) 18(1) C(11) 36(1) 41(1) 39(1) 9(1) 3(1) 17(1) C(12) 42(1) 39(1) 41(1) 7(1) 0(1) 18(1) C(13) 35(1) 45(1) 56(1) 10(1) 1(1) 16(1) C(14) 42(1) 44(1) 57(1) 13(1) 10(1) 15(1) C(15) 54(1) 60(1) 62(1) 31(1) 10(1) 25(1) C(16) 42(1) 58(1) 53(1) 22(1) 4(1) 24(1) C(17) 42(1) 46(1) 43(1) 10(1) 4(1) 23(1) C(18) 50(1) 56(1) 46(1) 13(1) 2(1) 18(1) C(19) 63(1) 64(1) 61(1) 25(1) 9(1) 17(1) C(20) 78(1) 81(1) 52(1) 27(1) 18(1) 38(1) C(21) 93(2) 75(1) 44(1) 6(1) 8(1) 39(1) C(22) 70(1) 50(1) 54(1) 6(1) 6(1) 24(1) C(23) 49(1) 45(1) 51(1) 11(1) 8(1) 19(1) C(24) 54(1) 71(1) 72(1) 24(1) 11(1) 29(1) C(25) 43(1) 78(1) 103(2) 27(1) 15(1) 12(1) O(4) 43(1) 152(2) 86(1) 27(1) 7(1) 34(1) O(5) 52(1) 71(1) 72(1) 37(1) 21(1) 30(1) O(6) 97(1) 74(1) 80(1) 33(1) 3(1) 46(1)
84 Table S22. Anisotropic displacement parameters (Å ) for 3i. The anisotropic displacement factor exponent takes the form: 2 2 [ h 2 a* 2 U h k a* b* U 12 ] N(31) 52(1) 57(1) 61(1) 27(1) 21(1) 25(1) C(32) 49(1) 65(1) 41(1) 19(1) 10(1) 28(1) N(33) 49(1) 78(1) 46(1) 18(1) 0(1) 29(1) C(34) 47(1) 95(1) 56(1) 32(1) 12(1) 36(1) C(35) 69(1) 98(2) 60(1) 34(1) 24(1) 49(1) C(36) 115(2) 80(2) 55(1) 14(1) 20(1) 56(1) C(37) 100(2) 61(1) 73(2) 9(1) 9(1) 34(1) C(38) 69(1) 50(1) 79(1) 17(1) 10(1) 22(1) C(39) 57(1) 56(1) 52(1) 28(1) 14(1) 33(1) C(40) 52(1) 74(1) 46(1) 26(1) 10(1) 35(1) C(41) 46(1) 47(1) 37(1) 11(1) 2(1) 19(1) C(42) 47(1) 42(1) 42(1) 12(1) 3(1) 15(1) C(43) 50(1) 49(1) 54(1) 11(1) 2(1) 22(1) C(44) 68(1) 44(1) 48(1) 8(1) 8(1) 24(1) C(45) 70(1) 51(1) 49(1) 20(1) 6(1) 19(1) C(46) 53(1) 58(1) 50(1) 18(1) 8(1) 21(1) C47a 44(2) 61(2) 43(2) 9(2) 3(2) 14(2) C48a 53(2) 61(2) 44(2) 11(1) 5(1) 19(2) C49a 78(2) 61(2) 47(2) 14(2) 1(2) 24(2) C50a 100(3) 78(2) 39(2) 11(2) 6(2) 29(2) C51a 134(3) 78(2) 52(2) 1(2) 32(2) 28(2) C52a 109(3) 64(2) 65(2) 4(2) 21(2) 26(2) C47Bb 51(4) 73(4) 53(3) 10(3) 5(3) 12(4) C48Bb 64(4) 81(4) 47(3) 13(3) 2(3) 19(3) C49Bb 97(4) 84(4) 48(3) 20(3) 8(3) 11(3) C50Bb 103(4) 103(4) 49(3) 14(3) 7(3) 1(4) C51Bb 89(4) 110(4) 59(3) 9(3) 11(3) 18(4) C52Bb 71(4) 93(4) 63(3) 5(3) 6(3) 18(3) C(53) 65(1) 68(1) 64(1) 19(1) 3(1) 25(1) C(54) 51(1) 78(1) 79(1) 27(1) 19(1) 26(1) C(55) 125(2) 108(2) 123(2) 76(2) 1(2) 47(2)
85 Table S23. Hydrogen coordinates ( 10 4 ) and isotropic displacement parameters (Å ) for 3i x y z U(eq) H(1) 560(17) 9927(16) 4349(9) 57 H(2) H(5) H(6) H(7) H(8) H(13) H(15) H(16) H(18) H(19) H(20) H(21) H(22) H(23A) H(23B) H(24A) H(24B) H(24C) H(25A) H(25B) H(25C) H(31) 4661(16) 9723(17) 592(9) 64 H(32) H(35) H(36) H(37) H(38) H(43) H(45) H(46) H48a
86 H49a H50a H51a H52a H48Bb H49Bb H50Bb H51Bb H52Bb H(53A) H(53B) H(54A) H(54B) H(54C) H(55A) H(55B) H(55C) Table S24. Hydrogen bonds for 3i D H A d(d H) / Å d(h A) / Å d(d A) / Å < (DHA) / N(1)-H(1) O(2) 0.831(13) 2.611(16) 3.059(2) 115.2(14) C(13)-H(13) O(1)# (2) C(24)-H(24B) O(1)# (3) C(25)-H(25A) O(1)# (3) N(31)-H(31) O(5) 0.844(14) 2.534(17) 2.980(2) 114.1(14) C(43)-H(43) O(4)# (3) C(54)-H(54B) O(4)# (3) Symmetry transformations used to generate equivalent atoms: #1: x + 1, y, z; #2: x 1, y, z.
87 Figure S49. ORTEP structures of 3i.
88 Figure S50. Unit cell of the structure 3i.
89 Table S25. Crystal data and structure refinement for 3g Identification code 157XYZ14 (Solved by: R. A. Toscano) Project Title E 82 Empirical formula C 22 H 20 N 2 O 3 Formula weight Temperature / K 298(2) Wavelength / Å Crystal system monoclinic Space group P 21/c Unit cell dimensions a = (3) Å = 90 b = (7) Å = (12) c = (14) Å = 90 Volume / Å (6) Z 8 Density (calculated) / (Mg m -3 ) Absorption coefficient / mm F(000) 1520 Crystal size / color / shape mm / colorless / prism Theta range for data collection / to Index ranges 34 h 39, 10 k 10, 20 l 20 Reflections collected Independent reflections [R(int) = ] Completeness to theta = % Measurement device Bruker Smart Apex CCD diffractometer Absorption correction semi-empirical from equivalents Max. and min. transmission and Refinement method full-matrix least-squares on F 2 Data / restraints / parameters / 2 / 502
90 Goodness-of-fit on F Final R indices [I > 2 (I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole / e.å and Remarks crystal twinned or splitted Este producto no cumple las especificaciones del LRX-IQUI y se libera a solicitud expresa del usuario quien exime al laboratorio de toda responsabilidad de su uso.
91 Table S26. Atomic coordinates ( 10 4 ) and equivalent isotropic displacement parameters (Å ) for 3g. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor x y z U(eq) O(1) 3673(2) 3695(7) 4291(3) 65(2) O(2) 4018(2) 7285(6) 274(3) 60(2) O(3) 3749(2) 9807(6) 747(3) 69(2) N(1) 4102(2) 2272(7) 1960(4) 47(2) C(2) 3681(2) 3071(9) 2017(4) 42(2) N(3) 3524(2) 3046(7) 2909(3) 41(1) C(4) 3814(3) 3411(8) 3547(4) 44(2) C(5) 4605(3) 3631(10) 3999(5) 57(2) C(6) 5033(3) 3256(11) 3881(5) 66(2) C(7) 5163(3) 2471(11) 3130(7) 74(3) C(8) 4858(3) 2142(10) 2484(5) 56(2) C(9) 4418(2) 2562(8) 2583(4) 40(2) C(10) 4282(2) 3311(8) 3360(4) 41(2) C(11) 3693(2) 4918(8) 1670(4) 39(2) C(12) 3848(2) 5204(9) 841(4) 41(2) C(13) 3864(2) 6827(9) 518(4) 41(2) C(14) 3719(3) 8171(9) 1019(4) 47(2) C(15) 3565(3) 7877(9) 1826(4) 53(2) C(16) 3551(3) 6267(9) 2162(4) 52(2) C(17) 2882(2) 1220(9) 3166(4) 43(2) C(18) 3061(3) 156(10) 3788(5) 54(2) C(19) 2908(3) 1473(11) 3903(6) 66(2) C(20) 2574(3) 2062(13) 3397(6) 82(3) C(21) 2396(3) 1059(15) 2777(7) 102(4) C(22) 2545(3) 589(12) 2682(5) 69(3) C(23) 3050(2) 2982(9) 3045(4) 49(2) C(24) 4253(3) 6062(11) 760(5) 80(3) O(4) 1097(2) 4189(6) 638(3) 43(1) O(5) 1479(2) 3986(5) 3460(3) 42(1) O(6) 1239(2) 1665(6) 4541(3) 54(2) N(25) 1585(2) 581(7) 545(3) 39(1) C(26) 1159(2) 301(8) 935(3) 30(1)
92 N(27) 984(2) 1388(6) 722(3) 29(1) C(28) 1253(2) 2727(8) 694(3) 30(2) C(29) 2035(2) 3722(10) 712(4) 49(2) C(30) 2471(3) 3447(12) 583(5) 64(2) C(31) 2617(3) 1822(14) 382(5) 74(3) C(32) 2325(3) 501(11) 365(5) 57(2) C(33) 1882(2) 754(9) 530(4) 36(2) C(34) 1732(2) 2399(8) 686(4) 36(2) C(35) 1173(2) 608(7) 1911(3) 25(1) C(36) 1310(2) 2185(7) 2215(3) 28(1) C(37) 1331(2) 2504(7) 3093(4) 29(1) C(38) 1209(2) 1262(8) 3677(4) 36(2) C(39) 1068(2) 263(8) 3383(4) 44(2) C(40) 1049(2) 603(8) 2496(4) 37(2) C(41) 329(2) 1789(8) 245(4) 29(1) C(42) 512(2) 881(8) 924(4) 34(2) C(43) 334(2) 1037(9) 1744(4) 45(2) C(44) 18(3) 2086(10) 1894(5) 54(2) C(45) 200(2) 2985(9) 1243(5) 47(2) C(46) 27(2) 2834(8) 410(4) 37(2) C(47) 507(2) 1605(8) 670(4) 34(2) C(48) 1632(3) 5298(8) 2908(4) 56(2)
93 Table S28. Bond lengths and angles for 3g Bond length / Å O(1)-C(4) 1.259(8) C(17)-C(18) 1.391(10) O(2)-C(13) 1.372(7) C(17)-C(23) 1.503(10) O(2)-C(24) 1.430(9) C(18)-C(19) 1.387(11) O(3)-C(14) 1.370(8) C(18)-H(18) O(3)-H(3) 0.90(6) C(19)-C(20) 1.367(12) N(1)-C(9) 1.380(9) C(19)-H(19) N(1)-C(2) 1.438(9) C(20)-C(21) 1.360(13) N(1)-H(1) 0.99(5) C(20)-H(20) C(2)-N(3) 1.472(7) C(21)-C(22) 1.393(13) C(2)-C(11) 1.564(9) C(21)-H(21) C(2)-H(2) C(22)-H(22) N(3)-C(4) 1.355(9) C(23)-H(23A) N(3)-C(23) 1.467(8) C(23)-H(23B) C(4)-C(10) 1.463(10) C(24)-H(24A) C(5)-C(6) 1.356(11) C(24)-H(24B) C(5)-C(10) 1.416(10) C(24)-H(24C) C(5)-H(5) O(4)-C(28) 1.258(7) C(6)-C(7) 1.386(12) O(5)-C(37) 1.382(7) C(6)-H(6) O(5)-C(48) 1.431(7) C(7)-C(8) 1.387(11) O(6)-C(38) 1.383(7) C(7)-H(7) O(6)-H(6A) 0.90(6) C(8)-C(9) 1.396(10) N(25)-C(33) 1.395(8) C(8)-H(8) N(25)-C(26) 1.456(8) C(9)-C(10) 1.414(9) N(25)-H(25) 0.99(5) C(11)-C(16) 1.389(9) C(26)-N(27) 1.481(7) C(11)-C(12) 1.397(9) C(26)-C(35) 1.538(7) C(12)-C(13) 1.385(9) C(26)-H(26) C(12)-H(12) N(27)-C(28) 1.346(7) C(13)-C(14) 1.396(9) N(27)-C(47) 1.467(8) C(14)-C(15) 1.365(9) C(28)-C(34) 1.485(9) C(15)-C(16) 1.382(10) C(29)-C(30) 1.366(10) C(15)-H(15) C(29)-C(34) 1.399(9) C(16)-H(16) C(29)-H(29) C(17)-C(22) 1.366(10) C(30)-C(31) 1.401(12)
94 C(30)-H(30) C(41)-C(42) 1.401(8) C(31)-C(32) 1.375(12) C(41)-C(47) 1.526(8) C(31)-H(31) C(42)-C(43) 1.387(9) C(32)-C(33) 1.396(9) C(42)-H(42) C(32)-H(32) C(43)-C(44) 1.379(10) C(33)-C(34) 1.406(9) C(43)-H(43) C(35)-C(40) 1.381(8) C(44)-C(45) 1.363(10) C(35)-C(36) 1.400(8) C(44)-H(44) C(36)-C(37) 1.391(8) C(45)-C(46) 1.400(9) C(36)-H(36) C(45)-H(45) C(37)-C(38) 1.394(8) C(46)-H(46) C(38)-C(39) 1.363(8) C(47)-H(47A) C(39)-C(40) 1.407(8) C(47)-H(47B) C(39)-H(39) C(48)-H(48A) C(40)-H(40) C(48)-H(48B) C(41)-C(46) 1.389(9) C(48)-H(48C) Bond angle / C(13)-O(2)-C(24) 118.3(6) C(10)-C(5)-H(5) C(14)-O(3)-H(3) 118(6) C(5)-C(6)-C(7) 119.8(8) C(9)-N(1)-C(2) 120.1(6) C(5)-C(6)-H(6) C(9)-N(1)-H(1) 128(4) C(7)-C(6)-H(6) C(2)-N(1)-H(1) 111(4) C(6)-C(7)-C(8) 120.1(8) N(1)-C(2)-N(3) 110.6(5) C(6)-C(7)-H(7) N(1)-C(2)-C(11) 111.6(6) C(8)-C(7)-H(7) N(3)-C(2)-C(11) 110.4(5) C(7)-C(8)-C(9) 121.0(8) N(1)-C(2)-H(2) C(7)-C(8)-H(8) N(3)-C(2)-H(2) C(9)-C(8)-H(8) C(11)-C(2)-H(2) N(1)-C(9)-C(8) 123.4(6) C(4)-N(3)-C(23) 122.7(6) N(1)-C(9)-C(10) 117.6(7) C(4)-N(3)-C(2) 118.2(6) C(8)-C(9)-C(10) 119.1(7) C(23)-N(3)-C(2) 117.8(5) C(9)-C(10)-C(5) 117.9(7) O(1)-C(4)-N(3) 119.0(7) C(9)-C(10)-C(4) 119.2(6) O(1)-C(4)-C(10) 122.4(7) C(5)-C(10)-C(4) 121.7(6) N(3)-C(4)-C(10) 118.3(6) C(16)-C(11)-C(12) 119.6(6) C(6)-C(5)-C(10) 122.1(8) C(16)-C(11)-C(2) 121.6(6) C(6)-C(5)-H(5) C(12)-C(11)-C(2) 118.8(5)
95 C(13)-C(12)-C(11) 120.0(6) N(3)-C(23)-H(23B) C(13)-C(12)-H(12) C(17)-C(23)-H(23B) C(11)-C(12)-H(12) H(23A)-C(23)-H(23B) O(2)-C(13)-C(12) 125.9(6) O(2)-C(24)-H(24A) O(2)-C(13)-C(14) 114.3(6) O(2)-C(24)-H(24B) C(12)-C(13)-C(14) 119.8(6) H(24A)-C(24)-H(24B) C(15)-C(14)-O(3) 118.1(6) O(2)-C(24)-H(24C) C(15)-C(14)-C(13) 119.8(7) H(24A)-C(24)-H(24C) O(3)-C(14)-C(13) 122.0(6) H(24B)-C(24)-H(24C) C(14)-C(15)-C(16) 121.2(6) C(37)-O(5)-C(48) 118.6(5) C(14)-C(15)-H(15) C(38)-O(6)-H(6A) 113(5) C(16)-C(15)-H(15) C(33)-N(25)-C(26) 118.3(5) C(15)-C(16)-C(11) 119.6(6) C(33)-N(25)-H(25) 117(4) C(15)-C(16)-H(16) C(26)-N(25)-H(25) 118(4) C(11)-C(16)-H(16) N(25)-C(26)-N(27) 111.5(5) C(22)-C(17)-C(18) 116.7(7) N(25)-C(26)-C(35) 111.8(5) C(22)-C(17)-C(23) 121.9(7) N(27)-C(26)-C(35) 111.8(5) C(18)-C(17)-C(23) 121.4(7) N(25)-C(26)-H(26) C(19)-C(18)-C(17) 121.8(8) N(27)-C(26)-H(26) C(19)-C(18)-H(18) C(35)-C(26)-H(26) C(17)-C(18)-H(18) C(28)-N(27)-C(47) 120.8(5) C(20)-C(19)-C(18) 119.6(9) C(28)-N(27)-C(26) 120.2(5) C(20)-C(19)-H(19) C(47)-N(27)-C(26) 118.4(5) C(18)-C(19)-H(19) O(4)-C(28)-N(27) 119.9(6) C(21)-C(20)-C(19) 120.0(9) O(4)-C(28)-C(34) 122.3(6) C(21)-C(20)-H(20) N(27)-C(28)-C(34) 117.6(6) C(19)-C(20)-H(20) C(30)-C(29)-C(34) 121.3(8) C(20)-C(21)-C(22) 119.8(9) C(30)-C(29)-H(29) C(20)-C(21)-H(21) C(34)-C(29)-H(29) C(22)-C(21)-H(21) C(29)-C(30)-C(31) 119.5(8) C(17)-C(22)-C(21) 122.1(9) C(29)-C(30)-H(30) C(17)-C(22)-H(22) C(31)-C(30)-H(30) C(21)-C(22)-H(22) C(32)-C(31)-C(30) 120.0(8) N(3)-C(23)-C(17) 112.9(6) C(32)-C(31)-H(31) N(3)-C(23)-H(23A) C(30)-C(31)-H(31) C(17)-C(23)-H(23A) C(31)-C(32)-C(33) 121.0(8)
96 C(31)-C(32)-H(32) C(42)-C(41)-C(47) 120.9(6) C(33)-C(32)-H(32) C(43)-C(42)-C(41) 119.5(6) N(25)-C(33)-C(32) 121.7(7) C(43)-C(42)-H(42) N(25)-C(33)-C(34) 119.4(6) C(41)-C(42)-H(42) C(32)-C(33)-C(34) 118.9(7) C(44)-C(43)-C(42) 120.5(7) C(29)-C(34)-C(33) 119.2(6) C(44)-C(43)-H(43) C(29)-C(34)-C(28) 121.2(6) C(42)-C(43)-H(43) C(33)-C(34)-C(28) 119.1(6) C(45)-C(44)-C(43) 120.9(7) C(40)-C(35)-C(36) 118.9(5) C(45)-C(44)-H(44) C(40)-C(35)-C(26) 122.4(5) C(43)-C(44)-H(44) C(36)-C(35)-C(26) 118.7(5) C(44)-C(45)-C(46) 119.3(7) C(37)-C(36)-C(35) 120.3(5) C(44)-C(45)-H(45) C(37)-C(36)-H(36) C(46)-C(45)-H(45) C(35)-C(36)-H(36) C(41)-C(46)-C(45) 120.7(6) O(5)-C(37)-C(36) 124.9(5) C(41)-C(46)-H(46) O(5)-C(37)-C(38) 114.9(5) C(45)-C(46)-H(46) C(36)-C(37)-C(38) 120.1(5) N(27)-C(47)-C(41) 114.0(5) C(39)-C(38)-O(6) 123.3(5) N(27)-C(47)-H(47A) C(39)-C(38)-C(37) 119.7(5) C(41)-C(47)-H(47A) O(6)-C(38)-C(37) 117.0(5) N(27)-C(47)-H(47B) C(38)-C(39)-C(40) 120.6(5) C(41)-C(47)-H(47B) C(38)-C(39)-H(39) H(47A)-C(47)-H(47B) C(40)-C(39)-H(39) O(5)-C(48)-H(48A) C(35)-C(40)-C(39) 120.3(6) O(5)-C(48)-H(48B) C(35)-C(40)-H(40) H(48A)-C(48)-H(48B) C(39)-C(40)-H(40) O(5)-C(48)-H(48C) C(46)-C(41)-C(42) 119.0(6) H(48A)-C(48)-H(48C) C(46)-C(41)-C(47) 120.1(5) H(48B)-C(48)-H(48C) 109.5
97 Table S29. Anisotropic displacement parameters (Å ) for 3g. The anisotropic displacement factor exponent takes the form: -2 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 O(1) 75(4) 67(4) 51(3) 16(3) 12(3) 25(3) O(2) 95(4) 46(3) 38(3) 1(2) 14(3) 4(3) O(3) 137(6) 32(3) 38(3) 1(2) 0(3) 11(3) N(1) 61(4) 36(4) 44(3) 11(3) 3(3) 2(3) C(2) 52(5) 40(4) 33(4) 6(3) 1(3) 1(4) N(3) 47(4) 36(3) 39(3) 3(2) 3(3) 7(3) C(4) 65(6) 27(4) 42(4) 2(3) 3(4) 14(4) C(5) 62(6) 45(5) 64(5) 2(4) 2(4) 14(4) C(6) 72(7) 59(6) 67(6) 1(4) 16(5) 6(5) C(7) 50(6) 56(6) 115(8) 4(5) 12(5) 6(5) C(8) 67(6) 43(5) 60(5) 4(4) 4(4) 3(4) C(9) 56(5) 21(4) 45(4) 0(3) 1(3) 3(3) C(10) 52(5) 28(4) 43(4) 2(3) 2(3) 11(3) C(11) 43(4) 29(4) 45(4) 8(3) 5(3) 2(3) C(12) 46(5) 34(4) 43(4) 12(3) 2(3) 6(3) C(13) 52(5) 40(4) 31(3) 2(3) 3(3) 0(4) C(14) 61(5) 32(4) 48(4) 1(3) 0(4) 4(4) C(15) 78(6) 37(4) 44(4) 13(3) 11(4) 10(4) C(16) 78(6) 39(5) 39(4) 2(3) 18(4) 7(4) C(17) 24(4) 56(5) 49(4) 0(3) 12(3) 4(4) C(18) 55(5) 53(5) 54(5) 1(4) 5(4) 9(4) C(19) 59(6) 54(6) 85(6) 11(5) 6(5) 9(5) C(20) 69(7) 84(8) 94(7) 25(6) 1(5) 44(6) C(21) 72(7) 114(10) 118(9) 16(7) 28(6) 52(7) C(22) 40(5) 93(8) 74(6) 25(5) 11(4) 25(5) C(23) 51(5) 49(5) 46(4) 1(3) 7(3) 3(4) C(24) 116(8) 68(6) 57(5) 16(4) 36(5) 4(6) O(4) 57(3) 30(3) 42(3) 9(2) 7(2) 0(2) O(5) 71(4) 23(3) 34(2) 3(2) 4(2) 13(2) O(6) 111(5) 26(3) 25(2) 1(2) 4(2) 18(3) N(25) 55(4) 34(3) 29(3) 3(2) 7(3) 4(3) C(26) 37(4) 25(4) 28(3) 7(2) 2(3) 7(3)
98 N(27) 32(3) 22(3) 34(3) 4(2) 1(2) 5(2) C(28) 44(4) 32(4) 15(3) 1(2) 3(2) 5(3) C(29) 47(5) 56(5) 43(4) 6(3) 5(3) 18(4) C(30) 50(6) 80(7) 63(5) 5(5) 13(4) 32(5) C(31) 30(5) 122(9) 68(6) 1(6) 19(4) 10(6) C(32) 49(5) 72(6) 50(5) 6(4) 17(4) 5(5) C(33) 38(4) 46(5) 24(3) 3(3) 3(3) 4(3) C(34) 38(4) 41(4) 28(3) 0(3) 6(3) 12(3) C(35) 27(3) 25(3) 24(3) 1(2) 1(2) 2(3) C(36) 30(4) 21(3) 32(3) 6(2) 3(2) 4(3) C(37) 37(4) 16(3) 33(3) 3(2) 1(3) 2(3) C(38) 57(5) 23(4) 29(3) 3(3) 6(3) 3(3) C(39) 84(6) 25(4) 22(3) 7(3) 8(3) 13(4) C(40) 58(5) 18(3) 36(4) 2(3) 1(3) 8(3) C(41) 29(4) 27(4) 31(3) 2(2) 0(2) 5(3) C(42) 37(4) 34(4) 33(3) 3(3) 1(3) 3(3) C(43) 57(5) 46(5) 31(4) 5(3) 1(3) 14(4) C(44) 61(6) 55(5) 44(4) 17(4) 14(4) 22(4) C(45) 46(5) 42(5) 54(5) 15(4) 11(4) 4(4) C(46) 36(4) 31(4) 46(4) 5(3) 1(3) 2(3) C(47) 35(4) 35(4) 31(3) 9(3) 2(3) 4(3) C(48) 94(7) 25(4) 48(4) 3(3) 6(4) 15(4)
99 Table S30. Hydrogen coordinates ( 10 4 ) and isotropic displacement parameters (Å ) for 3g x y z U(eq) H(3) 3730(30) 10010(120) 180(40) 103 H(1) 4110(20) 1440(80) 1490(40) 56 H(2) H(5) H(6) H(7) H(8) H(12) H(15) H(16) H(18) H(19) H(20) H(21) H(22) H(23A) H(23B) H(24A) H(24B) H(24C) H(6A) 1230(30) 750(90) 4880(50) 81 H(25) 1610(20) 1440(70) 80(40) 47 H(26) H(29) H(30) H(31) H(32) H(36) H(39) H(40) H(42) H(43)
100 H(44) H(45) H(46) H(47A) H(47B) H(48A) H(48B) H(48C) H(42) Table S31. Hydrogen bonds for 3g D H A d(d H) / Å d(h A) / Å d(d A) / Å < (DHA) / O(3)-H(3) O(1)#1 0.90(6) 1.73(7) 2.568(7) 153(9) N(1)-H(1) O(3)#2 0.99(5) 2.04(6) 2.917(8) 146(6) O(6)-H(6A) O(4)#3 0.90(6) 1.76(6) 2.642(6) 166(8) N(25)-H(25) O(5)#4 0.99(5) 2.57(6) 3.275(6) 128(5) N(25)-H(25) O(6)#4 0.99(5) 2.05(6) 2.882(7) 139(5) Symmetry transformations used to generate equivalent atoms: #1: x, y + 3/2, z 1/2; #2: x, y 1, z; #3: x, y + 1/2, z + 1/2; #4: x, y 1/2, z 1/2.
101 Figure S51. ORTEP structure of 3g.
102 Figure S52. Unit cell of the structure 3g. References 1. Shaabani, A.; Afshari, R.; Hooshmand, S. E.; New J. Chem. 2017, 4, Wang, S.; Yin, S.; Xia, S.; Shi, Y.; Tu, S. Rong, L.; Green Chem. Lett. Rev. 2012, 5, Jiang, Ch.; Yang, L.; Wu, W. T.; Guo, Q. L.; You, Q. D.; Bioorg. Med. Chem. 2011, 19, Chernobrovin, N. I.; Kozhevnikov, Y. V.; Zalesov, V. S.; Dolbilkin, K. V.; Razepina, T. G.; USSR SU Shanton, K. J.; Azizian, F.; Eur. Pat. Appl. EP A Andrew, J. S.; Meegan, M. J.; Sobolev, V.; Frost, D.; Zisterer, D. M.; Williams, D. C.; Lloyd, D. G.; J. Med. Chem. 2007, 50, 5301.
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