2-Chloro-N-(3-methyl­phen­yl)benzamide

Vinola Z Rodrigues; B Thimme Gowda; Viktor Vrábel; Jozef Kožíšek

doi:10.1107/S1600536812005739

. 2012 Feb 17;68(Pt 3):o723. doi: 10.1107/S1600536812005739

2-Chloro-N-(3-methylphenyl)benzamide

Vinola Z Rodrigues ^a, B Thimme Gowda ^a,^*, Viktor Vrábel ^b, Jozef Kožíšek ^b

PMCID: PMC3295494 PMID: 22412605

Abstract

In the structure of the title compound, C₁₄H₁₂ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the aniline ring is positioned anti to the N—H bond. The amide group forms dihedral angles of 60.1 (1) and 22.0 (1)°, respectively, with the benzoyl and aniline rings, while the angle between these rings is 38.7 (1)°. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which give rise to infinite chains running along the c axis.

Related literature

For studies, including ours, on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (1999 ▶, 2006 ▶); Rodrigues et al. (2011 ▶); Saeed et al. (2010 ▶); for N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶); for N-chloroarylamides, see: Jyothi & Gowda (2004 ▶); and for N-bromoarylsulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO
M _r = 245.70
Tetragonal,
a = 8.8751 (3) Å
c = 15.9642 (5) Å
V = 1257.45 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 295 K
0.4 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.898, T _max = 0.942
8244 measured reflections
2552 independent reflections
1757 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.069
S = 1.04
2552 reflections
158 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.08 e Å⁻³
Δρ_min = −0.11 e Å⁻³
Absolute structure: Flack (1983 ▶), 1229 Friedel pairs
Flack parameter: 0.00 (6)

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: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005739/sj5196sup1.cif

e-68-0o723-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005739/sj5196Isup2.hkl

e-68-0o723-Isup2.hkl^{(125.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812005739/sj5196Isup3.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—H1⋯O1ⁱ	0.86 (1)	2.03 (1)	2.8790 (16)	171 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship. VV and JK thank the Grant Agencies for their financial support (VEGA Grant Agency of the Slovak Ministry of Education, grant No. 1/0679/11), the Research and Development Agency of Slovakia (grant No. APVV-0202–10) and Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

supplementary crystallographic information

Comment

The amide and sulfonamide moieties are the constituents of many biologically important 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., 1999, 2006; Rodrigues et al., 2011; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of 2-chloro-N-(3-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, while the meta-methyl group in the anilino ring is positioned anti to the N—H bond, similar to that observed in 3-chloro-N-(3-methylphenyl)benzamide (I) (Rodrigues et al., 2011).

The amide group forms dihedral angles of 60.1 (1) and 22.0 (1)°, respectively, with the benzoyl and aniline rings, while the angle between the benzoyl and aniline rings is 38.7 (1)°, compared to the value of 77.4 (1)° in (II).

In the crystal structure, intermolecular N1—H1···O1 hydrogen bonds (Table 1) 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 by a method similar to the one described by Gowda et al. (2006). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.

Plate like colorless single crystals of the title compound used in the X-ray diffraction studies were obtained by slow evaporation of an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.