N-(4-Chloro­phen­yl)-3,4,5-trimethoxy­benzamide

Aamer Saeed; Rasheed Ahmad Khera; Mahira Batool; Uzma Shaheen; Ulrich Flörke

doi:10.1107/S1600536808023234

. 2008 Jul 31;64(Pt 8):o1625. doi: 10.1107/S1600536808023234

N-(4-Chlorophenyl)-3,4,5-trimethoxybenzamide

Aamer Saeed ^a,^*, Rasheed Ahmad Khera ^a, Mahira Batool ^a, Uzma Shaheen ^a, Ulrich Flörke ^b

PMCID: PMC2962079 PMID: 21203315

Abstract

In the title compound, C₁₆H₁₆ClNO₄, the dihedral angle between the two aromatic rings is 67.33 (8)°. The crystal packing shows strong intermolecular N—H⋯O hydrogen bonds that link the molecules to form chains along [ Inline graphic 01].

Related literature

For related literature, see: Capdeville et al. (2002 ▶); Ho et al. (2002 ▶); Igawa et al. (1999 ▶); Jackson et al. (1994 ▶); Makino et al. (2003 ▶); Zhichkin et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₆ClNO₄
M _r = 321.75
Monoclinic,
a = 9.487 (2) Å
b = 25.666 (6) Å
c = 6.9781 (15) Å
β = 112.340 (5)°
V = 1571.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 (2) K
0.41 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.901, T _max = 0.975
6765 measured reflections
3581 independent reflections
3104 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.106
S = 1.02
3581 reflections
202 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1780 Friedel pairs
Flack parameter: 0.06 (6)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023234/bt2747sup1.cif

e-64-o1625-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023234/bt2747Isup2.hkl

e-64-o1625-Isup2.hkl^{(175.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.18	2.878 (3)	136

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Symmetry code: (i) Inline graphic .

Acknowledgments

AS gratefully acknowledges a research grant from Quaid-I-Azam University, Islamabad.

supplementary crystallographic information

Comment

The benzanilide core is present in compounds with a wide range of biological activities that it has been called a privileged structure. Benzanilides serve as intermediates towards benzothiadiazin-4-ones (Makino et al., 2003), benzodiazepine-2,5-diones (Ho et al., 20022), and 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as centroid elements of ligands that bind to a wide variety of receptor types. Thus benzanilides containing aminoalkyl groups originally designed as a peptidomimetic, have been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinases (Capdeville et al., 2002). Benzamides have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999)

Geometric parameters of the title compound, C₁₆H₁₆ClNO₄, are in the usual ranges. The dihedral angle between the two aromatic rings is 67.33 (8)° and the torsion angles N1—C1—C2—C3 and C1—N1—C11—C12 are -31.1 (3)° and -39.2 (4)°, respectively. Of the three methoxy groups two of them lie nearly in plane with the aromatic ring, the O(3) group is almost perpendicular with C9—O3—C5—C4 of 92.2 (3)°. The crystal packing shows strong intermolecular N—H···O bonds that link molecules to endless chains along [-101]. Details are given in Table 1.

Experimental

Trimethoxybenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 4-chloroaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 4 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq 1 M HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (84%) as white needles: IR (KBr) 3226, 1665, 1616, 1520, 1352 cm^-1; 1H NMR (CDCl₃, 400 MHz) δ 8.13 (d, J = 8 Hz, 1H), 7.81 (d, J = 8 Hz, 1H), 7.51 (dd, J = 8 Hz, 1H), 7.66 (dd, J = 8 Hz, 1H), 7.43 (d, J = 8 Hz, 2H), 7.36 (br s, 1H), 7.25 (d, J = 8 Hz, 1H), 3.89 (9H, s, OMex3). Anal. Calcd. For C₁₆H₁₆ClNO₄, C, 59.73; H, 5.01; 11.02; N, 4.35; found C, 59.69; H, 5.04; 11.02; N, 4.42