Supporting Information

Organic Hydrogen-bondedassembly of Asymmetric Phenol Amide Molecules

Lin Li, Zhuan Fei, Xiang-gao Meng,Li-ping Cao,Qun Cai, Ren-qiang Sunand An-xin Wu*

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education,College of Chemistry, CentralChinaNormalUniVersity, Wuhan 430079,People’s Republic of China

N-(4-hydroxyphenyl)benzamide(1)1

m.p.210-213°C1H NMR (d6-DMSO, 600 MHz): δ10.03 (s, 1H), 9.27 (s, 1H), 7.94 (d, J = 7.2 Hz, 2H), 7.55 (m, 5H), 6.75 (d, J = 8.4 Hz, 2H).13C NMR (d6-DMSO, 150 MHz): δ170.09, 158.86, 140.32, 136.42, 135.84, 133.45, 132.67, 127.41, 120.15.IR(KBr,cm-1): 3328,3054, 1649, 1538, 1510, 1435, 1369, 1319, 1247, 1226, 1168, 1102, 825, 719, 690, 542.

N-(4-hydroxyphenyl)-4-nitrobenzamide(2)2

m.p.263-265°C.1H NMR (d6-DMSO, 600 MHz):δ10.39 (s, 1H), 9.43 (s, 1H), 8.36 (d, J = 7.6 Hz, 2H), 8.16 (d, J = 7.1 Hz, 2H), 7.55 (s, 2H), 6.77 (d, J = 6.8 Hz, 2H). 13C NMR (d6-DMSO, 150 MHz):δ168.41, 154.16,145.96, 134.19, 128.72, 127.57, 127.46, 120.27, 120.18. IR(KBr,cm-1): 3410, 3386, 1661, 1601, 1551, 1515, 1346, 1256, 1101, 849, 829, 711, 587, 516, 435.

N-(4-hydroxyphenyl)-2-nitrobenzamide(3)

m.p.211-213°C1H NMR (d6-DMSO, 600 MHz):δ10.40 (s, 1H), 9.30 (s, 1H), 8.11 (d, J = 7.9 Hz, 1H), 7.91(m, 1H),7.73 (t, J = 7.4 Hz, 2H),7.45 (d, J = 8.8 Hz, 2H), 6.75 (d, J = 8.8 Hz, 2H). 13C NMR (d6-DMSO, 150 MHz):δ168.56, 159.02, 151.78, 138.02, 135.60, 129.78, 126.62, 120.40, 120.20. IR(KBr,cm-1): 3350, 3296, 1651, 1602, 1542, 1513, 1448, 1354, 1319, 1266, 1224, 838, 792, 734, 697, 638, 525.HRMS (ESI): m/z [M+H]+calcd for C13H11N2O4: 259.07; found: 259.07.

N-(4-hydroxyphenyl)-4-methylbenzamide(4)3

m.p.190°C.1H NMR (d6-DMSO, 600 MHz):δ 9.94 (s, 1H), 9.24 (s, 1H), 7.85 (d, J = 7.7 Hz, 2H), 7.53 (d, J= 8.4 Hz, 2H), 7.32 (d, J=6.6 Hz, 2H), 6.74 (d, J = 7.2 Hz, 2H), 2.39 (s, 3H).13C NMR (d6-DMSO,150 MHz): δ169.72, 158.57, 146.13, 137.22, 135.70, 133.80, 132.48, 127.27, 119.89, 25.93.IR(KBr,cm-1): 3331,3391,2920,1648,1613,1539,1514,1436,1380,1322,1229,829,544.

N-(4-hydroxyphenyl)cinnamamide(5)3

m.p.118°C.1H NMR (d6-DMSO, 600 MHz):δ 10.02 (s, 1H), 9.31 (s, 1H), 7.62 (d, J = 7.3 Hz, 2H), 7.55 (s, 1H), 7.53 (s, 1H), 7.50 (d, J= 8.9 Hz, 2H), 7.45 (t, J = 7.4 Hz, 2H), 7.41 (d, J = 7.1 Hz, 1H), 6.80 (d, J= 15.7 Hz, 1H), 6.74 (d, J = 8.8 Hz, 2H). 13C NMR (d6-DMSO, 150 MHz):δ 163.10, 153.57, 140.28, 139.13, 135.07, 131.14, 129.83, 129.38, 128.73, 128.09, 127.70, 121.66, 121.10, 120.52, 115.88, 114.86. IR(KBr,cm-1): 3301, 3026, 2787,2691,1654,1621,1596,1556,1509,1436,1358,1261,1228,1192,988,760,677,539,520,482.

N-(4-hydroxyphenyl)methacrylamide(6)4

m.p.155-156°C. 1H NMR (d6-DMSO, 600 MHz):δ 9.54 (s, 1H), 9.25 (s, 1H), 7.44 (d, J = 7.2 Hz, 2H), 6.72 (d, J = 7.8 Hz, 2H), 5.76 (s, 1H), 5.45 (s, 1H), 1.94 (s, 3H). 13C NMR (d6-DMSO, 150 MHz): δ171.44, 158.66, 145.63, 135.65, 127.30, 124.51, 120.03, 23.89. IR(KBr,cm-1):3288, 3199, 1647, 1605,1589,1541,1508,1439, 1272,1212,1167,831, 521.

N-(4-hydroxyphenyl)propionamide(7)5

m.p.173°C. 1H NMR (d6-DMSO, 600 MHz):δ9.58 (s, H), 9.13(s, H), 7.36 (d, J = 8.4 Hz, 2H), 6.68 (d, J = 8.4 Hz, 2H), 2.24 (q, J = 7.8 Hz, 2H), 1.06(t, J = 7.8 Hz, 3H). 13C NMR (d6-DMSO, 150 MHz):δ 171.24, 153.06, 131.09, 120.91, 114.99, 29.36, 9.92.IR(KBr,cm-1): 3310,3160,2976,2935,1650,1609,1563,1508,1435,1260,1219,921,839,782,716,693,525.

N-(4-hydroxyphenethyl)acetamide(8)6

m.p.129-131°C.1H NMR (d6-DMSO, 600 MHz):δ 9.19 (s, 1H), 7.89 (s, 1H), 6.99 (d, J = 8.4 Hz, 2H), 6.69 (d, J = 8.4 Hz, 2H), 3.19 (d, J = 7.5 Hz, 2H), 2.58 (s, 2H), 1.79 (s, 3H).13C NMR (d6-DMSO, 150 MHz): δ 169.06, 155.63, 129.46, 115.11, 40.63, 34.46, 22.65. IR(KBr,cm-1): 3338,3100,3043,3014,2934,2810,2698,2625,2511,1637,1594,1567,1514,1460,1361,1247,1104,856,812,601,551,493.

N-(4-hydroxyphenethyl)propionamide(9)7

m.p.89-90°C.1H NMR (d6-DMSO, 600 MHz):δ 7.70 (s, 1H), 6.99 (d, J = 8.0 Hz, 2H), 6.81 (d, J = 8.0 Hz, 2H), 5.78 (s, 1H), 3.46 (dd, J = 6.3 Hz, 2H), 2.71 (t, J = 6.8 Hz, 2H), 2.17 (q, J = 7.8 Hz, 2H), 1.11 (t, J = 7.8 Hz, 3H).13C NMR (d6-DMSO, 150 MHz):δ 174.84, 155.39, 129.93, 115.80, 41.12, 34.83, 29.94, 9.75. IR(KBr,cm-1):3328, 2354, 1640, 1602, 1545, 1512, 1487, 1448, 1371, 1314, 1237, 1190, 1121, 1071, 992, 955, 864, 825, 777, 695, 612, 566,566, 520.

N-(4-hydroxyphenethyl)benzamide(10)8

m.p.164°C. 1H NMR (d6-DMSO, 600 MHz):δ 9.21 (s, 1H), 8.55 (s, 1H), 7.84 (d, J = 6.6 Hz, 2H), 7.46 (m, 3H), 7.04 (d, J = 6.6 Hz, 2H), 6.70 (d, J = 7.2 Hz, 2H), 3.43 (d, J = 6.0 Hz, 2H), 2.74 (t, J = 6.6 Hz, 2H).13C NMR (d6-DMSO, 150 MHz):δ171.20, 160.74, 139.77, 136.14, 134.63, 133.35, 132.22, 120.27, 120.18, 46.38, 39.46.IR(KBr,cm-1): 3342, 1887, 1634, 1589, 1566, 1513, 1464, 1386, 1362, 1273, 1249, 1118, 1073, 991, 956, 891, 859, 839, 818, 621, 556, 517, 499, 465.

N-(4-hydroxyphenethyl)-4-methylbenzamide(11)9

m.p.157-159°C.1H NMR (d6-DMSO, 600 MHz):δ 9.25 (s, 1H), 8.48 (s, 1H), 7.74 (d, J = 8.0 Hz, 2H), 7.28 (d, J = 8.0 Hz, 2H), 7.05 (d, J = 8.3 Hz, 2H), 3.41 (d, J = 6.0 Hz, 2H), 2.73 (t, J = 6.6 Hz,2H), 2.37 (s, 3H).13C NMR (d6-DMSO, 150 MHz):δ 165.97, 155.43, 140.88, 131.78, 129.61, 129.50, 128.76, 127.10, 115.09, 41.21, 34.34, 20.90. IR(KBr,cm-1):3332, 2922, 2874, 2801, 2679,2603, 1619, 1548, 1512, 1457, 1269, 1251,1237, 1047, 877, 824, 750, 558.

Figure S1. The one–dimensional molecular C11(9) chain with in 3.

Figure S2.Two–dimensional molecular sheet with fused R44 (26) ring in 11. The carbon bonded H atoms are omitted for clarity.

Figure S3.Two –dimensional molecular sheet with fused R44 (26) ring in 5. The carbon bonded H atoms are omitted for clarity.

Figure S4.Two –dimensional molecular sheet with fused R44 (26)ring in 8. The carbon bonded H atoms are omitted for clarity.

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