4-Chloro-N-m-tolyl­benzamide

Aamer Saeed; Madiha Irfan; Michael Bolte

doi:10.1107/S1600536809018236

. 2009 May 20;65(Pt 6):o1334. doi: 10.1107/S1600536809018236

4-Chloro-N-m-tolylbenzamide

Aamer Saeed ^a,^*, Madiha Irfan ^a, Michael Bolte ^b

PMCID: PMC2969756 PMID: 21583188

Abstract

In the title compound, C₁₄H₁₂ClNO, the dihedral angle between the two aromatic rings is 11.29 (15)°. The crystal packing is stabilized by N—H⋯O hydrogen bonds linking the molecules into chains running along the c axis.

Related literature

For the biological activity of N-substituted benzamides and benzanilide derivatives, see Calderone et al. (2006 ▶); Beccalli et al. (2005 ▶); Yoo et al. (2005 ▶); Vega-Noverola et al. (1989 ▶); Olsson et al. (2002 ▶); Lindgren et al. (2001 ▶); Zhichkin et al. (2007 ▶). For related structures see: Saeed et al. (2008 ▶); Chopra & Guru Row (2008 ▶); Donnelly et al. (2008 ▶)

Experimental

Crystal data

C₁₄H₁₂ClNO
M _r = 245.70
Monoclinic,
a = 13.9721 (14) Å
b = 10.1922 (6) Å
c = 9.0154 (8) Å
β = 105.415 (7)°
V = 1237.67 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 173 K
0.26 × 0.24 × 0.23 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T _min = 0.928, T _max = 0.936
9469 measured reflections
2193 independent reflections
1787 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.178
S = 1.04
2193 reflections
160 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018236/ya2096sup1.cif

e-65-o1334-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018236/ya2096Isup2.hkl

e-65-o1334-Isup2.hkl^{(107.8KB, 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 (3)	1.99 (3)	2.854 (3)	166 (3)

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Symmetry code: (i) Inline graphic .

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. N-Substituted benzamides are well known anticancer compounds and the mechanism of action for N-substituted benzamide-induced apoptosis has been studied, using declopramide as a lead compound (Olsson et al., 2002). N-Substituted benzamides inhibit the activity of nuclear factor- B and nuclear factor of activated T cells activity while inducing activator protein 1 activity in T lymphocytes (Lindgren et al., 2001). Various N-substituted benzamides exhibit potent antiemetic activity (Vega-Noverola et al., 1989), while heterocyclic analogs of benzanilide derivatives are potassium channel activators (Calderone et al., 2006). o-Aryloxylation of N-substituted benzamides induced by the copper(II)/trimethylamine N-oxide system has been studied. 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). A one-pot conversion of 2-nitro-n-arylbenzamides to 2,3-dihydro-1H-quinazoline-4-ones has also been reported (Yoo et al., 2005). As part of our work on the structure of benzanilides and related compounds, we report here the structure of the title 4-chlorobenzamide derivative, I, Fig 1.

The dihedral angle between the two aromatic rings is 11.29 (15) °. The crystal packing is stabilized by N—H···O hydrogen bonds linking the molecules to chains running along the c axis.

Experimental

4-Chlorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 3-methylaniline (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 from CHCl₃ afforded the title compound (81%) as colourless blocks. Anal. calcd. for C₁₄H₁₂Cl_NO1: C 68.44, H 4.92, N 5.70%; found: C 68.39, H 4.90, N 5.67%