Journal of Chemical Crystallography
Hz, 1H, Ph),7.33 (td, J=7.7, 1.7 Hz, 1H, Ph). FT-IR (KBr
disc, cm−1): υas(N–H) 3265, υ(C=O) 1649, δ(N–H) 1587,
υ(C–C) 1557 and 1527, β(C–H) 1307 and 1259, γ(C–H)
664–801.
3,5-Dichloro-N-benzyl benzamide (11)
White powder, yield: 47.7 mg (71%). The calculated of
elemental analysis (%): C 59.98, H 3.93, N 5.00; found of
elemental analysis (%): C 59.88, H 3.73, N 5.12. 1H NMR
(400 MHz, DMSO-d6): δ(ppm) 9.26 (t, J = 5.8 Hz, 1H,
–NH–), 7.91 (d, J = 1.9 Hz, 2H, Ph), 7.82 (t, J = 1.9 Hz,
1H, Ph), 7.35–7.30 (m, 4H, Ph), 7.28–7.22 (m, 1H, Ph),
4.47 (d, J = 5.9 Hz, 2H, –CH2). FT-IR (KBr disc, cm−1):
υas(N–H) 3269, υas(CH2) 3071, υs(CH2) 3065, υ(C–H) 3027,
υ(C=O) 1636, υ(C–C) 1566 and 1549, β(C–H) 1288 and
1233, γ(C–H) 693–866.
3,5-Dichloro-N-(2,6-dimethylphenyl) benzamide (7)
White powder, yield: 52.2 mg (74%). The calculated of
elemental analysis (%): C 61.19, H 4.42, N 4.76; found of
elemental analysis (%): C 61.34, H 4.68, N 4.27. 1H NMR
(400 MHz, DMSO-d6): δ(ppm) 9.99 (s, 1H, –NH–), 8.00
(d, J = 1.9 Hz, 2H, Ph), 7.91 (t, J = 1.9 Hz, 1H, Ph), 7.88
(t, J = 1.9 Hz, 1H, Ph), 7.86 (d, J = 2.0 Hz, 1H, Ph), 2.17
(s, 6H, –CH3). FT-IR (KBr disc, cm−1): υas(N–H) 3427,
υ(CH3) 3074 and 2920, υ(C=O) 1652, υ(C–C) 1572 and
1521, β(C–H) 1307 and 1283, γ(C–H) 649–867.
3,5-Dichloro-N-(4-nitrophenyl)-benzamide (12)
Bright yellow powder, yield: 56.7 mg (76%). The calcu-
lated of elemental analysis (%): C 50.15, H 2.58, N 9.00;
found of elemental analysis (%): C 51.00, H 2.63, N 9.15. 1H
NMR (400 MHz, DMSO-d6): δ(ppm) 10.93 (s, 1H, –NH–),
8.31–8.29 (m, 1H, Ph), 8.28–8.26 (m, 1H, Ph), 8.04 (s, 1H,
Ph), 8.02 (d, J =2.1 Hz, 1H, Ph), 8.00 (d, J=1.9 Hz, 2H,
Ph), 7.91 (dd, J=3.9, 1.9 Hz, 1H, Ph),7.85 (d, J=2.0 Hz,
1H, Ph). FT-IR (KBr disc, cm−1): υas(N–H) 3437, υ(C–H)
3268, υ(C=O) 1634, υ(C–C) 1566 and 1542, υas(NO2) 1506,
υs(NO2) 1384, β(C–H) 1328 and 1295, γ(C–H) 688–858.
3,5-Dichloro-N-(4-iodophenyl) benzamide (8)
White powder, yield: 83.3 mg (89%). The calculated of ele-
mental analysis (%): C 39.77, H 2.04, N 3.57; found of ele-
mental analysis (%): C 38.97, H 2.34, N 3.24. 1H NMR (400
MHz, DMSO-d6): δ(ppm) 10.49 (s, 1H, –NH–), 7.96 (d,
J=1.9 Hz, 2H, Ph), 7.90–7.81 (m, 1H, Ph), 7.81–7.68 (m,
2H, Ph), 7.68–7.52 (m, 2H, Ph). FT-IR (KBr disc, cm−1):
υas(N–H) 3448, υ(C–H) 3080 and 3059, υs(N–H) 2922,
υ(C=O) 1653, υ(C–C) 1585, 1566, 1518 and 1487, υ(C=N)
1390, β(C–H) 1310, 1287 and 1259, γ(C–H) 688–871.
3,5-Dichloro-N-(2,6-diisopropylphenyl) benzamide (13)
Light pink powder, yield: 52.9 mg (63%). The calculated of
elemental analysis (%): C 61.67, H 6.00, N 8.00; found of
elemental analysis (%): C 61.74, H 6.05, N 7.78. 1H NMR
(400 MHz, DMSO-d6): δ(ppm) 10.00 (s, 1H, –NH–), 8.00
(d, J=1.9 Hz, 2H, Ph), 7.94 (s, 1H, Ph), 7.87 (s, 1H, Ph),
3.06–2.98 (m, 2H, –CH–), 1.12 (dd, J=6.8 Hz, 12H, –CH3).
FT-IR (KBr disc, cm−1): υas(N–H) 3437, υ(C–H) 2977,
υ(C=O) 1648, β(C–H) 1126 and 1072, γ(C–H) 603–727.
3,5-Dichloro-N-(3-iodophenyl) benzamide (9)
White powder, yield: 77.2 mg (82%). The calculated of
elemental analysis (%): C 39.77, H 2.04, N 3.57; found of
elemental analysis (%): C 38.09, H 2.44, N 3.56. 1H NMR
(400 MHz, DMSO-d6): δ(ppm) 10.45 (s, 1H, –NH–), 8.20
(s, 1H, Ph), 7.96 (d, J = 1.6 Hz, 2H, Ph), 7.76 (d, J = 7.6
Hz, 1H, Ph), 7.87 (d, J =1.7 Hz, 1H, Ph), 7.48 (d, J=7.8
Hz, 1H, Ph), 7.17 (dd, J=9.8, 6.2 Hz, 1H, Ph). FT-IR (KBr
disc, cm−1): υas(N–H) 3452, υs(N–H) 3267, υ(C=O) 1643,
υ(C–C) 1584, 1565 and 1541, υ(C=N) 1474, β(C–H) 1319,
1262 and 1259, γ(C–H) 678–803.
3,5-Dichloro-N-(2,4,6-trimethylphenyl) benzamide (14)
Beige powder, yield: 57.9 mg (70%). The calculated of
elemental analysis (%): C 55.71, H 4.35, N 4.06; found of
elemental analysis (%): C 54.83, H 4.43, N 4.68. 1H NMR
(400 MHz, DMSO-d6): δ(ppm) 9.90 (s, 1H, : –NH–), 7.99
(d, J=1.9 Hz, 2H, Ph), 7.89–7.85 (m, 1H, Ph), 6.93 (s, 2H,
Ph), 2.25 (s, 3H, –CH3), 2.10 (s, 6H, –CH3). FT-IR (KBr
disc, cm−1): υas(N–H) 3440, υ(C–H) 2977, υ(C–H) 3027,
υ(C=O) 1642, υ(C–C) 1561 and 1520, β(C–H) 1307 and
1300, γ(C–H) 707.
3,5-Dichloro-N-(2-iodophenyl) benzamide (10)
White powder, yield: 73.4 mg, (78%). The calculated of
elemental analysis (%): C 39.77, H 2.04, N 3.57; found of
elemental analysis (%): C 38.77, H 2.74, N 3.39. 1H NMR
(400 MHz, DMSO-d6): δ(ppm) 10.34 (s, 1H, –NH–), 8.00
(d, J=1.8 Hz, 2H, Ph), 7.97–7.89 (m, 2H, Ph), 7.49–7.39
(m, 2H, Ph),7.12–7.06 (m, 1H, Ph). FT-IR (KBr disc, cm−1):
υas(N–H) 3459, υ(C=O) 1636, υ(C=N) 1303, β(C–H) 1126
and 1053, γ(C–H) 612.
X‑ray Crystallography
A summary of crystallographic data and experimental
details for 3,5-dichloro-N-(4-chlorophenyl)benzamide (4)
1 3