SUPPLEMENTARY MATERIAL. A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine Hybrids
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- Καϊάφας Σπηλιωτόπουλος
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1 /CH17272_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(12), SUPPLEMENTARY MATERIAL A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine Hybrids Garima Khanna, A Pooja Saluja, A and Jitender M. Khurana A,B A Department of Chemistry, University of Delhi, Delhi , India. B Corresponding author. jmkhurana@chemistry.du.ac.in 1
2 Spectral data 7-(4-Chlorophenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IIa) Pale yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2891, 1478, 1208, 1093; 1 H NMR (400 MHz, CDCl3) δ = (m, 2H, ArH), (m, 2H, ArH), 6.43 (s, 1H, ArH), 6.33 (s, 1H, ArH), 5.84 (s, 2H, CH2), 5.21 (s, 2H, CH2), 4.46 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , 98.88, 79.31, 50.56; HRMS (ESI) calcd. for C15H12ClNO3 [M + H] + : , found: [M + H] +. 7-(4-Methylphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IIb) Pale yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2888, 1472, 1187, 1034; 1 H NMR (400 MHz, CDCl3) δ = (m, 4H, ArH), 6.44 (s, 1H, ArH), 6.33 (s, 1H, ArH), 5.83(s, 2H, CH2), 5.23 (s, 2H, CH2), 4.46 (s, 2H, CH2), 2.25 (s, 3H, CH3); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , 98.84, 79.98, 50.59, 20.52; HRMS (ESI) calcd. for C16H16NO3 [M + H] + : , found: [M + H] +. 7-(4-Fluorophenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IIc) Pale yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2894, 1472, 1209, 1037; 1 H NMR (400 MHz, CDCl3) δ = (m, 2H, ArH), (m, 2H, ArH), 6.43 (s, 1H, ArH), 6.34 (s, 1H, ArH), 5.84 (s, 2H, CH2), 5.19 (s, 2H, CH2), 4.44 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = (d, 1 JC-F = 239 Hz), , , , , (d, 3 JC-F = 7.6 Hz), (d, 2 JC-F = 22 Hz), , , , 98.85, 80.16, 51.02; HRMS (ESI) calcd. for C15H12FNO3 [M + H] + : , found: [M + H] +. 7-(4-Methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IId) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2897, 1509, 1478, 1215, 1038; 1 H NMR (400 MHz, CDCl3) δ = 7.03 (s, 2H, J = 8.4 Hz, ArH), (d, 2H, J = 8.4 Hz, ArH), 6.43 (s, 1H, ArH), 6.34 (s, 1H, ArH), 5.84 (s, 2H, CH2), 5.18 (s, 2H, CH2), 4.42 (s, 2H, CH2), 3.73 (s, 3H, OCH3); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , 98.84, 80.71, 55.48, 51.10; HRMS (ESI) calcd. for C16H15NO4 [M + H] + : , found: [M + H] +. 7-(3-Chloro-4-fluorophenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2- e][1,3]oxazine (IIe) 2
3 Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2893, 1474, 1208, 1039; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), (m, 1H, ArH), (m, 1H, ArH), 6.42 (s, 1H, ArH), 6.35 (s, 1H, ArH), 5.85 (s, 2H, CH2), 5.18 (s, 2H, CH2), 4.44 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = (d, 1 JC-F = 242 Hz), , , (d, 4 JC-F = 2.8 Hz), , , (d, 3 JC-F = 6.7 Hz), (d, 2 JC-F = 22 Hz), , , , 98.95, 79.54, 50.98; HRMS (ESI) calcd. for C15H11ClFNO3 [M+ H] + : , found: [M + H] +, [M + H + 2] +. 7-(3-Cyanophenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IIf) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2900, 2224, 1480, 1218, 1055; 1 H NMR (400 MHz, CDCl3) δ = (m, 4H, ArH), 6.47 (s, 1H, ArH), 6.37 (s, 1H, ArH), 5.87 (s, 2H, CH2), 5.27 (s, 2H, CH2), 4.53 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , , , 98.97, 78.45, 50.31; HRMS (ESI) calcd. for C16H12N2O3 [M + H] + : , found: [M + H] +. 7-(4-Bromophenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IIg) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2892, 1483, 1212, 1047; 1 H NMR (400 MHz, CDCl3) δ = 7.32 (d, 2H, J = 8.4Hz, ArH), 6.94 (d, 2H, J = 9.2 Hz, ArH), 6.43 (s, 1H, ArH), 6.33 (s, 1H, ArH), 5.84 (s, 2H, CH2), 5.22 (s, 2H, CH2), 4.46 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , 98.90, 79.19, 50.51; HRMS (ESI) calcd. for C15H12BrNO3 [M + H] + : , found: [M + H] +, [M + H + 2] + 7-(3,4-Dichlorophenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IIh) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2892, 1474, 1211, 1044; 1 H NMR (400 MHz, CDCl3) δ = 7.20 (d, 1H, J = 9.2 Hz, ArH), 7.07 (s, 1H, ArH), 6.83 (d, 1H, J = 6.8 Hz), 6.37(s, 1H, ArH), 6.28 (s, 1H, ArH), 5.79 (s, 2H, CH2), 5.13 (s, 2H, CH2), 4.39 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , , 98.96, 78.69, 50.46; HRMS (ESI) calcd. for C15H11Cl2NO3 [M + H] + : , found: [M + H] +, [M + H + 2] +, [M + H + 4] +. 7-(4-Iodophenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IIi) 3
4 Pale yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2890, 1480, 1212, 1044; 1 H NMR (400 MHz, CDCl3) δ = 7.51 (d, 2H, J = 8.4 Hz, ArH), 6.83 (d, 2H, J = 8.4 Hz, ArH), 6.43 (s, 1H, ArH), 6.33 (s, 1H, ArH), 5.84 (s, 2H, CH2), 5.21 (s, 2H, CH2), 4.46 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , 98.91, 83.85, 78.97, 50.36; HRMS (ESI) calcd. for C15H12INO3 [M + H] + : , found: [M + H] +. 7-(3-Nitrophenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IIj) Yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2895, 1526, 1478, 1212, 1044; 1 H NMR (400 MHz, CDCl3) δ = 7.88 (s, 1H, ArH), (m, 1H, ArH), (m, 2H, ArH), 6.47 (s, 1H, ArH), 6.36 (s, 1H, ArH), 5.85 (s, 2H, CH2), 5.30 (s, 2H, CH2), 4.57 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , , 99.02, 78.32, 50.74; HRMS (ESI) calcd. for C15H12N2O5 [M + H] + : , found: [M + H] +. Methyl 4-(6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazin-7(8H)-yl)benzoate (IIk) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2880, 1698, 1479, 1185, 1059; 1 H NMR (400 MHz, CDCl3) δ = (m, 2H, ArH), (m, 2H, ArH), 6.41 (s, 1H, ArH), 6.31 (s, 1H, ArH), 5.80 (s, 2H, CH2), 5.24 (s, 2H, CH2), 4.50 (s, 2H, CH2), 3.79 (s, 3H, COOMe); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , 99.01, 77.73, 51.79, 49.56; HRMS (ESI) calcd. for C17H15NO5 [M + H] + : , found: [M + H] +. 7-(4-Nitrophenyl)-7,8-dihydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-e][1,3]oxazine (IIl) Yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 1598, 1485, 1212, 1060; 1 H NMR (400 MHz, DMSO-d6) δ = 8.07 (d, 2H, J = 8.4 Hz, ArH), 7.20 (d, 2H, J = 8.4 Hz, ArH), 6.69 (s, 1H, ArH), 6.43 (s, 1H, ArH), 5.88 (s, 2H, CH2), 5.45 (s, 2H, CH2), 4.65 (s, 2H, CH2); 13 C NMR (100 MHz, DMSO-d6) δ = , , , , , , , , , , 98.50, 76.47, 47.79; HRMS (ESI) calcd. for C15H12N2O5 [M + H] + : , found: [M + H] +. 2-(4-Chlorophenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIa) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2840, 1591, 1217, 1039; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), 8.01 (d, 1H, J = 8.4 Hz, ArH), 7.90 (d, 1H, J = 9.2 Hz, ArH), (m, 1H), (m, 3H, ArH), (m, 2H, ArH), 5.39 (s, 2h, CH2), 4.90 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , 4
5 147.14, , , , , , , , , , , 79.60, 48.06; HRMS (ESI) calcd. for C17H13ClN2O [M + H] + : , found: [M + H] +, [M + H + 2] +. 2-(4-Methylphenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIb) Pale yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 1506, 1226, 1099; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), 8.01 (d, 1H, J = 8.4 Hz, ArH), 7.89 (d, 1H, J = 9.2 Hz, ArH), (m, 1H, ArH), (m, 1H, ArH), (m, 4H, ArH), 5.40 (s, 2H, CH2), 4.89 (s, 2H, CH2), 2.25 (s, 3H, CH3); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , , , 80.15, 47.96, 20.51; HRMS (ESI) calcd. for C18H16N2O [M + H] + : , found: [M + H] +. 2-(4-Fluorophenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIc) Pale yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2891, 1503, 1223, 1046; 1 H NMR (400 MHz, CDCl3) δ = 8.76 (s, 1H, ArH), (m, 2H, ArH), (m, 6H, ArH), 5.33 (s, 2H, CH2), 4.84 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = (d, 1 JC-F = 241 Hz), , , , , , , , , , (d, 3 JC-F = 7.6 Hz), (d, 2 JC-F = 22 Hz), , 80.34, 48.40; HRMS (ESI) calcd. for C17H13FN2O [M + H] + : , found: [M + H] +. 2-(4-Methoxyphenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIId) Pale green solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2835, 1505, 1234, 1032; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), (m, 2H, ArH), (m, 1H, ArH), 7.32 (d, 1H, J = 9.2 Hz, ArH), (m, 2H, ArH), (m, 2H, ArH), 5.33 (s, 2H, CH2), 4.83 (s, 2H, CH2), 3.66 (s, 3H, OCH3); , , , , , , , , , , 121,14, , , 81.11, 55.43, 48.43; HRMS (ESI) calcd. for C18H16N2O2 [M + H] + : , found: [M + H] +. 2-(3-Chloro-4-fluorophenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIe) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 1497, 1224, 1048; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), 7.98 (d, 1H, J = 8.4 Hz, ArH), 7.90 (d, 1H, J = 9.2 Hz, ArH), (m, 1H, ArH), (m, 1H, ArH), (m, 1H, ArH), (m, 2H, ArH), 5.33 (s, 2H, CH2), 4.86 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = (d, 1 JC-F = 242 Hz), , , (d, 4 JC-F = 3 Hz), , , , , , , , (d, 3 JC-F = 6.7 Hz), (d, 2 JC-F = 22 Hz), 5
6 111.58, 79.64, 48.49; HRMS (ESI) calcd. for C17H12ClFN2O [M + H] + : , found: [M + H] +, [M + H + 2] + 2-(3-Cyanophenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIf) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2853, 2229, 1601, 1485, 1234, 1047; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), 7.98 (d, 1H, J = 8.4 Hz, ArH), 7.87 (d, 1H, J = 8.8 Hz, ArH), (m, 4H, ArH), (m, 2H, ArH), 5.37 (s, 2H, CH2), 4.89 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , , , , , , 78.57, 47.99; HRMS (ESI) calcd. for C18H13N3O [M + H] + : , found: [M + H] +. 2-(4-Bromophenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIg) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2853, 1587, 1493, 1216, 1043; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), 8.01 (d, 1H, J = 8.4 Hz, ArH), 7.90 (d, 1H, J = 8.4 Hz, ArH), (m, 3H, ArH), (m, 1H, ArH), 7.01 (d, 2H, J = 8.4 Hz, ArH), 5.38 (s, 2H,CH2), 4.89 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , , , 79.38, 47.94; HRMS (ESI) calcd. for C17H13BrN2O [M + H] + : , found: [M + H] +, [M + H + 2] +. 2-(3,4-Dichlorophenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIh) Light yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2895, 1591, 1229, 1011; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), 8.02 (d, 1H, J = 8.4 Hz, ArH), 7.92 (d, 1H, J = 9.2 Hz, ArH), (m, 1H, ArH), (m, 2H, ArH), (m, 1H, ArH), (m, 1H, ArH), 5.36 (s, 2H, CH2), 4.88 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , , , , 78.88, 48.05; HRMS (ESI) calcd. for C17H12Cl2N2O [M + H] + : , found: [M + H] +, [M + H + 2] +, [M + H + 4] + 2-(3-Nitrophenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIi) Yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 1526, 1231, 1045; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), 8.07 (d, 1H, J = 8.4 Hz, ArH), (m, 2H, ArH), 7.75 (d, 1H, J = 7.6 Hz, ArH), (m, 3H, ArH), (m, 1H, ArH), 5.46 (s, 2H, CH2), 4.99 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , , , , 6
7 111.59, 78.38, 48.07; HRMS (ESI) calcd. for C17H13N3O3 [M + H] + : , found: [M + H] +. 2-(4-Iodophenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIj) Yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2851, 1585, 1228, 1045; 1 H NMR (400 MHz, CDCl3) δ = 8.80 (m, 1H, ArH), 8.02 (d, 1H, J = 8.4 Hz, ArH), 7.91 (d, 1H, J = 8.8 Hz), (m, 1H, ArH), (m, 1H, ArH), (m, 1H, ArH), (m, 1H, ArH), 5.39 (s, 2H, CH2), 4.90 (s, 2H, CH2); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , 84.40, 79.19, 47.83; HRMS (ESI) calcd. for C17H13IN2O [M + H] + : , found: [M + H] +. Methyl 4-(1H-[1,3]oxazino[5,6-f]quinolin-2(3H)-yl)benzoate (IIIk) Pale yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 2884, 1707, 1609, 1268, 1052; 1 H NMR (400 MHz, CDCl3) δ = (m, 1H, ArH), (m, 4H, ArH), (m, 1H, ArH), 7.23 (m, 1H, ArH), 7.06 (d, 2H, J = 9.2 Hz, ArH), 5.42 (s, 2H, CH2), 4.94 (s, 2H, CH2), 3.79 (s, 3H, CH3); 13 C NMR (100 MHz, CDCl3) δ = , , , , , , , , , , , , 77.97, 51.85, 47.24; HRMS (ESI) calcd. for C19H16N2O3 [M + H] + : , found: [M + H] +. 2-(4-Nitrophenyl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIl) Yellow solid; m.p K (decompose); IR (νmax cm 1 ) (CHCl3): 1596, 1505, 1271, 1043; 1 H NMR (400 MHz, DMSO-d6) δ = (m, 1H, ArH), 8.38 (d, 1H, J = 8.4 Hz, ArH), 8.09 (d, 2H, J = 9.2 Hz, ArH), 7.81 (d, 1H, J = 9.2 Hz, ArH), (m, 1H, ArH), (m, 2H, ArH), 7.29 (d, 1H, J = 9.2 Hz, ArH), 5.65 (s, 2H, CH2), 5,13 (s, 2H, CH2); 13 C NMR (100 MHz, DMSO-d6) δ =152.78, , , , , , , , , , , , , 76.55, 45.81; HRMS (ESI) calcd. for C17H13N3O3 [M + H] + : , found: [M + H] +. 2-(Pyridin-3-yl)-2,3-dihydro-1H-[1,3]oxazino[5,6-f]quinoline (IIIm, C 16 H 13 N 3 O) Light pink solid; m.p.: K (decompose); IR (νmax cm 1 ) (CHCl3): 2924, 1579, 1498, 1229, 1045; 1 H NMR (400 MHz, DMSO-d6) δ = (m, 1H, ArH), 8.52 (d, 1H, J = 3.2 Hz, ArH), 8.12 (d, 1H, J = 4.4 Hz, ArH), 8.00 (d, 1H, J = 8.4 Hz, ArH), 7.90 (d, 1H, J = 9.2 Hz, ArH), (m, 2H, ArH), (m, 1H, ArH), (m, 1H, ArH), 5.42 (s, 2H, CH2), 4.94 (s, 2H, CH2); 13 C NMR (100 MHz, DMSO-d6) δ =152.15, , , 7
8 144.36, , , , , , , , , , , 78.97, 47.87; HRMS (ESI) calcd. for C16H13N3O [M + H] + : , found: [M + H] +. 8
9 Table S1: Crystal data and structure refinement for IIa Formula C 15 H 12 ClNO 3 Formula weight (g) Temperature Wavelength 293(2) K Å Crystal system, space group Monoclinic, I 1 a 1 Unit cell dimensions a = (7)Å alpha = 90 deg. b = (2) Å c = (10) Å Volume (11)Å 3 Z, Calculated density 4, 1.70 g/cm 3 Absorption coefficient mm -1 F(000) 600 Crystal size Theta range for data collection Limiting indices 0.22 x 0.20 x 0.16 mm to deg. beta = (5) deg. gamma = 90 deg. -18<=h<=17, -6<=k<=6, -24<=l<=25 Reflections collected / unique 3123 / 1407 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 3123 / 0 / 182 Goodness-of-fit on F^ Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.a -3 9
10 Table S2: Crystal data and structure refinement for IIIa Formula C 34 H 26 Cl 2 N 4 O 2 Formula weight (g) Temperature 293(2) K Wavelength Å Crystal system, space group Triclinic, P -1 Unit cell dimensions a = (6)Å α = (7) deg. b = (9) Å β = (7) deg. c = (15) Å γ = (7) deg. Volume (2)Å 3 Z, Calculated density 2, g/cm 3 Absorption coefficient mm -1 F(000) 616 Crystal size 0.04 x 0.02 x 0.01 mm Theta range for data collection 2.95 to deg. Limiting indices -10<=h<=10, -15<=k<=15, -24<=l<=2 Reflections collected / unique 6711 / 3195 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 3195 / 0 / 379 Goodness-of-fit on F^ Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.a -3 10
11 1 H NMR Spectrum of IIa 11
12 13 C NMR Spectrum of IIa 12
13 1 H NMR Spectrum of IIb 13
14 13 C NMR spectrum of IIb 14
15 1 H NMR spectrum of IIc 15
16 13 C NMR spectrum of IIc 16
17 1 H NMR spectrum of IId 17
18 13 C NMR spectrum of IId 18
19 1 H NMR spectrum of IIe 19
20 13 C NMR spectrum of IIe 20
21 1 H NMR spectrum of IIf 21
22 13 C NMR spectrum of IIf 22
23 1 H NMR spectrum of IIg 23
24 13 C NMR spectrum of IIg 24
25 1 H NMR spectrum of IIh 25
26 13 C NMR spectrum of IIh 26
27 1 H NMR spectrum of IIi 27
28 13 C NMR spectrum of IIi 28
29 1 H NMR spectrum of IIj 29
30 13 C NMR spectrum of IIj 30
31 1 H NMR spectrum of IIk 31
32 13 C NMR spectrum of IIk 32
33 1 H NMR spectrum of IIl 33
34 13 C NMR spectrum of IIl 34
35 1 H NMR spectrum of IIIa 35
36 13 C NMR spectrum of IIIa 36
37 1 H NMR spectrum of IIIb 37
38 13 C NMR spectrum of IIIb 38
39 1 H NMR spectrum of IIIc 39
40 13 C NMR spectrum of IIIc 40
41 1 H NMR spectrum of IIId 41
42 13 C NMR spectrum of IIId 42
43 1 H NMR spectrum of IIIe 43
44 13 C NMR spectrum of IIIe 44
45 1 H NMR spectrum of IIIf 45
46 13 C NMR spectrum of IIIf 46
47 1 H NMR spectrum of IIIg 47
48 13 C NMR spectrum of IIIg 48
49 1 H NMR spectrum of IIIh 49
50 13 C NMR spectrum of IIIh 50
51 1 H NMR spectrum of IIIi 51
52 13 C NMR spectrum of IIIi 52
53 1 H NMR spectrum of IIIj 53
54 13 C NMR spectrum of IIIj 54
55 1 H NMR spectrum of IIIk 55
56 13 C NMR spectrum of IIIk 56
57 1 H NMR spectrum of IIIl 57
58 13 C NMR spectrum of IIIl 58
59 1 H NMR spectrum of IIIm 59
60 13 C NMR spectrum of IIIm 60
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