N-(2,6-Dichloro­phen­yl)-4-methyl­benzamide

Vinola Z Rodrigues; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811028935

. 2011 Jul 23;67(Pt 8):o2123. doi: 10.1107/S1600536811028935

N-(2,6-Dichlorophenyl)-4-methylbenzamide

Vinola Z Rodrigues ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3213564 PMID: 22091141

Abstract

In the title compound, C₁₄H₁₁Cl₂NO, the two aromatic rings are nearly orthogonal to each other [dihedral angle 79.7 (1)°], while the central amide core –NH—C(=O)– is nearly coplanar with the benzoyl ring [N—C—C—C torsion angles = −5.5 (3) and 1772. (2)°]. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [001].

Related literature

For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2006 ▶, 2009 ▶), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004 ▶) and on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ▶).

Experimental

Crystal data

C₁₄H₁₁Cl₂NO
M _r = 280.14
Tetragonal,
a = 16.4706 (8) Å
c = 19.8709 (9) Å
V = 5390.6 (4) Å³
Z = 16
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 293 K
0.48 × 0.34 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.807, T _max = 0.937
5852 measured reflections
2752 independent reflections
1701 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.120
S = 1.01
2752 reflections
166 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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 datablock(s) I, global. DOI: 10.1107/S1600536811028935/bt6816sup1.cif

e-67-o2123-sup1.cif^{(17KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028935/bt6816Isup2.hkl

e-67-o2123-Isup2.hkl^{(135.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811028935/bt6816Isup3.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—H1N⋯O1ⁱ	0.82 (2)	2.08 (2)	2.878 (2)	164 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

VZR thanks the University Grants Commission, Government of India, New Delhi, for award of an RFSMS research fellowship.

supplementary crystallographic information

Comment

The amide moiety is an important constituent of many biologically significant compounds. As part of our studies on the effects of ring and side chain substitutions on the structures of N-(aryl)-amides (Bhat & Gowda, 2000; Gowda et al., 2006, 2009), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004) and N-(aryl)-arylsulfonamides (Gowda et al., 2005), the crystal structure of N-(2,6-dichlorophenyl)-4-methylbenzamide (I) has been determined (Fig. 1). The conformations of the N—H and C=O bonds in the amide segment of the structure are anti to each other, similar to that observed in N-(2,6-dimethylphenyl)-4-methylbenzamide (II) (Gowda et al., 2009) and other benzanilides, with similar bond parameters.

The two aromatic rings in the structure make the dihedral angle of 79.7 (1)°, compared to the value of 78.8 (1)° in (II). The central amide core –NH—C(=O)– is nearly coplanar with the benzoyl ring. The orientation of the anilino ring with respect to the amide core are given by the torsion angles, C2—C1—N1—C7 = 105.8 (3)° and C6—C1—N1—C7 = -74.5 (3)°.

Part of the crystal structure of (I), showing the formation of hydrogen- bonded layered chains (Table 1) running along b axis is shown in Fig.2.

Experimental

The title compound was prepared by the method described by Gowda et al. (2009). The purity of the compound was checked and characterized by recording its infrared and NMR spectra.

Needle-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.