N-(2-Chloro­phen­yl)-4-methyl­benzamide

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

doi:10.1107/S1600536811038840

. 2011 Sep 30;67(Pt 10):o2767. doi: 10.1107/S1600536811038840

N-(2-Chlorophenyl)-4-methylbenzamide

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

PMCID: PMC3201415 PMID: 22065132

Abstract

The asymmetric unit of the title compound, C₁₄H₁₂ClNO, contains two independent molecules in which the dihedral angles between the two aromatic rings are 51.76 (6) and 51.48 (7)°. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, which link the molecules into chains running along the c axis.

Related literature

For preparation of the title compound, see: Gowda et al. (2003 ▶). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004 ▶); Bowes et al. (2003 ▶); Gowda et al. (2001 ▶); Rodrigues et al. (2011 ▶); Saeed et al. (2010 ▶) on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶) and on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO
M _r = 245.70
Monoclinic,
a = 9.6940 (5) Å
b = 27.4495 (9) Å
c = 9.9025 (4) Å
β = 106.730 (5)°
V = 2523.48 (19) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 K
0.97 × 0.13 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶) based on expressions derived by Clark & Reid (1995 ▶)] T _min = 0.957, T _max = 0.972
47577 measured reflections
7045 independent reflections
2850 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.126
S = 0.85
7045 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 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/S1600536811038840/bt5650sup1.cif

e-67-o2767-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038840/bt5650Isup2.hkl

e-67-o2767-Isup2.hkl^{(320.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811038840/bt5650Isup3.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
N15—H15A⋯O34	0.86	2.02	2.8408 (16)	159
N32—H32A⋯O17ⁱ	0.86	2.01	2.8455 (16)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

MF and JK thank the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency of Slovakia (APVV-0202–10) for their 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 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 work on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004; Bowes et al., 2003; Gowda et al., 2001; Saeed et al., 2010; Rodrigues et al., 2011), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-(aryl)-arylsulfonamides (Gowda et al., 2005), in the present work, the crystal structure of N-(2-Chlorophenyl)-4-methylbenzamide (I) has been determined (Fig.1). The asymmetric unit of (I) contains two independent molecules. In the crystal, the ortho-Cl substituent in the anilino ring is positioned syn to the N–H bond in one of the molecules and anti in the other molecule. Further, the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other in both the molecules, similar to that observed in N-(2-methylphenyl)- 4-methylbenzamide (II)(Rodrigues et al., 2011).

The packing of molecules linked by N—H···O hydrogen bonds into infinite chains 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. cuboid-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.