4-Chloro-N-(2-chloro­phen­yl)benzamide

Aamer Saeed; Rasheed Ahmad Khera; Kazuma Gotoh; Hiroyuki Ishida

doi:10.1107/S1600536808028882

. 2008 Sep 13;64(Pt 10):o1934. doi: 10.1107/S1600536808028882

4-Chloro-N-(2-chlorophenyl)benzamide

Aamer Saeed ^a,^*, Rasheed Ahmad Khera ^a, Kazuma Gotoh ^b, Hiroyuki Ishida ^b

PMCID: PMC2959385 PMID: 21201142

Abstract

In the molecular structure of the title compound, C₁₃H₉Cl₂NO, the amide N—C=O plane makes dihedral angles of 31.53 (8) and 36.23 (8)°, respectively, with the 4-chloro- and 2-chlorophenyl rings. The dihedral angle between the two benzene rings is 6.25 (8)°. The molecules are stacked in columns along the b axis through intermolecular N—H⋯O hydrogen bonds. The columns are further connected by weak C—H⋯O hydrogen bonds. The compound is not isomorphous with the fluoro analogue.

Related literature

For general background, see: Capdeville et al. (2002 ▶); Chopra & Row (2005 ▶); Ho et al. (2002 ▶); Igawa et al. (1999 ▶); Jackson et al. (1994 ▶); Makino et al. (2003 ▶); Zhichkin et al. (2007 ▶). For related structures, see: Chopra & Row (2005 ▶).

Experimental

Crystal data

C₁₃H₉Cl₂NO
M _r = 266.13
Monoclinic,
a = 10.7913 (14) Å
b = 4.8078 (6) Å
c = 23.570 (3) Å
β = 97.718 (3)°
V = 1211.8 (3) Å³
Z = 4
Mo- Kα radiation
μ = 0.52 mm⁻¹
T = 223 (1) K
0.35 × 0.31 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.884, T _max = 0.975
14924 measured reflections
3527 independent reflections
1847 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.154
S = 1.00
3527 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028882/bh2189sup1.cif

e-64-o1934-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028882/bh2189Isup2.hkl

e-64-o1934-Isup2.hkl^{(173KB, 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	0.85 (2)	2.12 (2)	2.901 (2)	154 (2)
C2—H2⋯O1ⁱⁱ	0.94	2.59	3.456 (3)	153

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Symmetry codes: (i) Inline graphic ; (ii) .

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, and for this reason 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., 2002), 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 peptidomimetic compounds, 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 kinase (Capdeville et al., 2002). Benzamides have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999).

In the crystal structure of the title compound (Fig. 1), the molecules are stacked in columns along the b cell-axis through intermolecular N—H···O hydrogen bonds (Table 1). The columns are also connected by weak C—H···O hydrogen bonds (Fig. 2). No significant π–π interactions are observed in the columns. The title compound is not isomorphous with the F analogue compound, 4-fluoro-N-(2-fluorophenyl)-benzamide, which exhibits a dimorphic behaviour, with non-centrosymmetric space groups P2₁ and Pca2₁ (Chopra & Row, 2005). The different crystal structures of the F analogue are probably originated from the intermolecular C—H···F interactions.

Experimental

4-Chorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 2-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%). Anal. calcd. for C₁₃H₉Cl₂NO: C 58.67, H 3.41, N 5.26%; found: C 58.23, H 3.46, N 5.08%.