4-Chloro-N-(3-methoxy­phen­yl)­benz­amide

Aamer Saeed; Rasheed Ahmad Khera; Naeem Abbas; Jim Simpson; Roderick G Stanley

doi:10.1107/S1600536808029899

. 2008 Sep 20;64(Pt 10):o1976. doi: 10.1107/S1600536808029899

4-Chloro-N-(3-methoxyphenyl)benzamide

Aamer Saeed ^a,^*, Rasheed Ahmad Khera ^a, Naeem Abbas ^a, Jim Simpson ^b, Roderick G Stanley ^b

PMCID: PMC2959436 PMID: 21201176

Abstract

The title benzamide derivative, C₁₄H₁₂ClNO₂, crystallizes with two independent molecules in the asymmetric unit. Both are close to being planar, with dihedral angles between the two benzene rings of 11.92 (6) and 12.80 (7)°. In the crystal structure, N—H⋯O hydrogen bonds link molecules into chains along a. These interactions are augmented by C—H⋯O hydrogen bonds to form two-dimensional layers in the ac plane. Additional C—H⋯O interactions result in a three-dimensional network consisting of undulating rows along c. The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio.

Related literature

For background on the applications of benzanilides, see: Zhichkin et al. (2007 ▶); Igawa et al. (1999 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO₂
M _r = 261.70
Orthorhombic,
a = 9.6952 (4) Å
b = 10.5671 (3) Å
c = 24.3512 (8) Å
V = 2494.78 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 91 (2) K
0.80 × 0.27 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T _min = 0.771, T _max = 0.948
47170 measured reflections
8997 independent reflections
8334 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.087
S = 1.05
8997 reflections
336 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ▶), 3581 Friedel pairs
Flack parameter: 0.59 (3)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶) and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029899/hb2792sup1.cif

e-64-o1976-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029899/hb2792Isup2.hkl

e-64-o1976-Isup2.hkl^{(440.1KB, 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
N1B—H1NB⋯O1A	0.887 (18)	1.977 (18)	2.8638 (13)	176.4 (15)
C3B—H3B⋯O1A	0.95	2.44	3.0436 (14)	121
C4B—H4B⋯O2A	0.95	2.59	3.5134 (15)	165
N1A—H1NA⋯O1Bⁱ	0.847 (18)	1.989 (18)	2.8309 (13)	172.0 (16)
C6A—H6A⋯O2Bⁱ	0.95	2.48	3.3885 (15)	161
C7A—H7A⋯O1Bⁱ	0.95	2.57	3.1611 (14)	121

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Symmetry code: (i) Inline graphic .

Acknowledgments

NA is grateful to the Higher Education Commission of Pakistan for financial support for a PhD programme. We also thank the University of Otago for purchase of the diffractometer.

supplementary crystallographic information

Comment

Benzanilides have important uses in organic synthesis (e.g. Zhichkin et al., 2007) and show biological activity (e.g. Igawa et al., 1999).

The title compound, (I), crystallized as an inversion twin in the crystal studied with two independent molecules, A and B, in the asymmetric unit. Bond distances and angles within the molecules are normal (Allen et al., 1987). Each molecule deviates slightly from planarity with dihedral angles between the two benzene rings of 11.92 (6)° for A and 12.80 (7)° for B.

In the crystal structure, N—H···O hydrogen bonds link molecules into chains along a (Table 1). These interactions are augmented by C—H···O hydrogen bonds to form two dimensional layers in the ac plane, Fig 2. Additional C—H···O interactions result in a three dimensional network consisting of undulating rows along c, Fig 3.

Experimental

4-Chorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 3-methoxyaniline (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 aqueous 1 M HCl and saturated aqueous NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue from CHCl₃ afforded the title compound (yield = 81%) as colourless needles: Analysis calculated. for C₁₄H₁₂Cl_NO₂: C 64.25, H 4.62, N 5.35%; found: C 64.19, H 4.68, N 5.30%.