4-Chloro-N-cyclo­hexyl­benzamide

Aamer Saeed; Rasheed Ahmad Khera; Muhammad Latif; Masood Parvez

doi:10.1107/S1600536809021217

. 2009 Jun 10;65(Pt 7):o1539. doi: 10.1107/S1600536809021217

4-Chloro-N-cyclohexylbenzamide

Aamer Saeed ^a, Rasheed Ahmad Khera ^a, Muhammad Latif ^b, Masood Parvez ^c,^*

PMCID: PMC2969216 PMID: 21582827

Abstract

In the title compound, C₁₃H₁₆ClNO, the cyclohexyl ring adopts a chair conformation, with puckering parameters Q = 0.576 (3) Å, θ = 0.1 (3) and ϕ = 8 (15)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link molecules into one-dimensional chains propagating in [010].

Related literature

For applications of N-substituted benzamides, see: Beccalli et al. (2005 ▶); Calderone et al. (2006 ▶); Vega-Noverola et al. (1989 ▶); Zhichkin et al. (2007 ▶); Lindgren et al. (2001 ▶); Olsson et al. (2002 ▶). For related crystal structures, see: Jones & Kuś (2004 ▶); Saeed et al. (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C₁₃H₁₆ClNO
M _r = 237.72
Monoclinic,
a = 14.755 (14) Å
b = 5.043 (7) Å
c = 16.818 (16) Å
β = 96.13 (6)°
V = 1244 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 173 K
0.12 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.967, T _max = 0.983
3651 measured reflections
2388 independent reflections
1497 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.151
S = 1.06
2388 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021217/lh2834sup1.cif

e-65-o1539-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021217/lh2834Isup2.hkl

e-65-o1539-Isup2.hkl^{(114.9KB, 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	2.06	2.901 (5)	160

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

N-Substituted benzamides, e.g., declopramideare, are well known anticancer compounds and the mechanism of benzamide-induced apoptosis has been studied, (Olsson et al., 2002). N-substituted benzamides inhibit the activity of nuclear factor-B and nuclear factor of activated T cells (Lindgren et al., 2001). Various N-substituted benzamides exhibit potent antiemetic activity (Vega-Noverola et al., 1989), while heterocyclic benzanilide are potassium channel activators (Calderone et al., 2006). N-Alkylated 2-nitrobenzamides are intermediates in the synthesis of dibenzo[b,e][1,4]diazepines (Zhichkin et al., 2007) and N-Acyl-2-nitrobenzamides are precursors of 2,3-disubstitued 3H-quinazoline-4-ones (Beccalli et al., 2005). As part of our work on the structure of benzanilides and related compounds, in this paper, we report the crystal structure of the title compound, (I).

The molecular structure of (I) is presented in Fig. 1. The molecular dimensions in (I) are normal (CSD version 5.30; Allen, 2002). The six-membered ring adopts a chair conformation with puckering parameters: Q = 0.576 (3) Å, θ = 0.1 (3)° and φ = 8(15)° (Cremer & Pople, 1975). The structure is stabilized by hydrogen bonding (N1–H1···O1) forming chains of molecules along the b-axis (details are in Table 1). The crystal structures of closely related compounds have been reported (Saeed et al., 2008; Jones & Kuś, 2004).

Experimental

4-Chlorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with cyclohexylamine (21.6 mmol) under a nitrogen atmosphere at reflux for 3 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 magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (87%) as colorless needles: Anal. calcd. for C₁₃H₁₆ClNO,: C, 65.68; H, 6.78; N, 5.89%; found: C, 65.61; H, 6.80; N, 5.91%.