2,4-Dichloro-N-cyclo­hexyl­benzamide

Aamer Saeed; Naeem Abbas; Shahid Hussain; Ulrich Flörke

doi:10.1107/S1600536808008131

. 2008 Apr 2;64(Pt 5):o773. doi: 10.1107/S1600536808008131

2,4-Dichloro-N-cyclohexylbenzamide

Aamer Saeed ^a,^*, Naeem Abbas ^a, Shahid Hussain ^a, Ulrich Flörke ^b

PMCID: PMC2961337 PMID: 21202267

Abstract

In the title molecule, C₁₃H₁₅Cl₂NO, the cyclohexane ring adopts a chair conformation. The aromatic ring plane is oriented with respect to the N/O/C plane at a dihedral angle of 51.88 (7)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into infinite chains along the [010] direction.

Related literature

For related literature, see: Makino et al. (2001 ▶, 2003 ▶); Ho et al. (2002 ▶); Zhichkin et al. (2007 ▶); Jackson et al. (1994 ▶); Capdeville et al. (2002 ▶); Manley et al. (2002 ▶); Igawa et al. (1999 ▶); Jones & Kuś (2004 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₃H₁₅Cl₂NO
M _r = 272.16
Monoclinic,
a = 26.135 (3) Å
b = 4.9144 (6) Å
c = 20.449 (2) Å
β = 90.167 (3)°
V = 2626.4 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 120 (2) K
0.48 × 0.17 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.803, T _max = 0.945
10950 measured reflections
3141 independent reflections
2389 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.110
S = 1.02
3141 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008131/hk2439sup1.cif

e-64-0o773-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008131/hk2439Isup2.hkl

e-64-0o773-Isup2.hkl^{(154.2KB, 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—H1B⋯O1ⁱ	0.88	1.95	2.796 (3)	161

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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 such 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), quinazoline-2,4-diones (Makino et al., 2001), benzodiazepine-2,5-diones (Ho et al., 2002) and 2,3-disubstituted-3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficancy 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). Pyridylmethyl containing benzanilides are vascular endothelial growth factor receptor and tyrosine kinase inhibitor (Manley et al., 2002). Furthermore, benzamides have been reported to have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999). We report herein the crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges. Ring A (C1–C6) is not planar, having total puckering amplitude, Q_T, of 0.575 (3) Å. It adopts chair conformation [φ = -177.97 (2)° and θ = 176.74 (3)°] (Cremer & Pople, 1975). Ring B (C8–C13) is, of course, planar and it is oriented with respect to the (N1/O1/C7) plane at a dihedral angle of 51.88 (7)°. The N1—C7—C8—C9 torsion angle is -130.16 (18)°. In N-cyclohexyl-4-(methoxycarbonyl)benzamide (Jones & Kuś, 2004), the corresponding torsion angles are reported as -17.9 (2)° and -45.2 (2)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into infinite chains along the [010] direction (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

A mixture of 2,4-dichlorobenzoyl chloride (65.7 mmol), cyclohexyl amine (86.9 mmol) and pyridine (20 ml) was left at 298 K for 15 h. Then, water (100 ml) was added and the resulting precipitates were collected. Recrystallization of the precipitates from benzene gave the title compound (yield; 75%).