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

Vinola Z Rodrigues; Peter Herich; B Thimme Gowda; Jozef Kožíšek

doi:10.1107/S1600536811041651

. 2011 Oct 12;67(Pt 11):o2940. doi: 10.1107/S1600536811041651

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

Vinola Z Rodrigues ^a, Peter Herich ^b, B Thimme Gowda ^a,^*, Jozef Kožíšek ^b

PMCID: PMC3247352 PMID: 22219970

Abstract

In the title compound, C₁₄H₁₂ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond. The benzoyl and aniline benzene rings are tilted relative to each other by 82.8 (1)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into infinite chains running along the c-axis direction.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (2000 ▶); Saeed et al. (2010 ▶), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005 ▶) and on N-chloro-arylsulfonamides, see: Gowda & Shetty (2004 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO
M _r = 245.70
Monoclinic,
a = 20.2969 (14) Å
b = 7.1850 (5) Å
c = 8.8662 (5) Å
β = 93.750 (5)°
V = 1290.22 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.92 × 0.28 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived from Clark & Reid (1995 ▶)] T _min = 0.911, T _max = 0.981
21209 measured reflections
3594 independent reflections
1870 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.138
S = 1.03
3594 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041651/bt5668sup1.cif

e-67-o2940-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041651/bt5668Isup2.hkl

e-67-o2940-Isup2.hkl^{(159.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041651/bt5668Isup3.cml

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—H1A⋯O1ⁱ	0.86	2.01	2.847 (2)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

PH and JK thank the VEGA Grant Agency of Slovak Ministry of Education 1/0679/11 and the Research and Development Agency of Slovakia (APVV-0202–10) for financial support and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship.

supplementary crystallographic information

Comment

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2000; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylsulfonamides (Gowda & Shetty, 2004), in the present work, the crystal structure of 2-chloro-N-(4-methylphenyl)benzamide (I) has been determined (Fig.1).

In (I), the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond and anti to the N–H bond of the C—NH—C(O)—C segment.

The central amide group –NHCO– is tilted to the anilino ring with the C9—C8—N1—C1 and C13—C8—N1—C1 torsion angles of -144.4 (2)° and 35.6 (3)°. The C3—C2—C1—N1 and C7—C2—C1—N1 torsion angles are -118.8 (2)° and 64.0 (3)°, respectively, while the C3—C2—C1—O1 and C7—C2—C1—O1 torsion angles are 61.8 (3)° and -115.4 (2)°, respectively. But the C2—C1—N1—C8 and C8—N1—C1—O1 torsion angles are 178.0 (2)° and -2.7 (3)°, respectively.

In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the c-axis. Part of the crystal structure is shown in Fig. 2.

Experimental

The title compound was prepared according to the method described by Gowda et al. (2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of an ethanol solution of the compound (0.5 g in 30 ml of ethanol) at room temperature.