N-(4-Chloro­phen­yl)-3-methyl­benzamide

B Thimme Gowda; Miroslav Tokarčík; Jozef Kožíšek; Vinola Zeena Rodrigues; Hartmut Fuess

doi:10.1107/S1600536809041956

. 2009 Oct 17;65(Pt 11):o2778. doi: 10.1107/S1600536809041956

N-(4-Chlorophenyl)-3-methylbenzamide

B Thimme Gowda ^a,^*, Miroslav Tokarčík ^b, Jozef Kožíšek ^b, Vinola Zeena Rodrigues ^a, Hartmut Fuess ^c

PMCID: PMC2971070 PMID: 21578371

Abstract

In the structure of the title compound, C₁₄H₁₂ClNO, the conformations of the N—H and C=O bonds are anti to each other. Furthermore, the conformation of the C=O bond is syn to the meta-methyl group in the benzoyl ring. The central –NH—C(=O)– amido group makes a dihedral angle of 32.4 (1)° with the benzoyl ring and 36.1 (1)° with the anilino ring. The dihedral angle between the two benzene rings is 68.4 (1)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains running along the a axis

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For related structures, see: Bowes et al. (2003 ▶); Gowda, Foro et al. (2008 ▶, 2009 ▶); Gowda, Tokarčík et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO
M _r = 245.7
Monoclinic,
a = 5.31325 (9) Å
b = 13.9256 (2) Å
c = 16.3497 (3) Å
β = 93.1799 (16)°
V = 1207.86 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 295 K
0.54 × 0.41 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur, Ruby, Gemini diffractometer
Absorption correction: analytical (CrysAlisPro; Oxford Diffraction, 2009 ▶) T _min = 0.842, T _max = 0.933
22561 measured reflections
2327 independent reflections
2083 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.093
S = 1.08
2327 reflections
160 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrysAlisPro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536809041956/om2285sup1.cif

e-65-o2778-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041956/om2285Isup2.hkl

e-65-o2778-Isup2.hkl^{(112KB, 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—H1N⋯O1ⁱ	0.864 (14)	2.298 (14)	3.1019 (16)	154.7 (15)

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Symmetry code: (i) Inline graphic .

Acknowledgments

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

supplementary crystallographic information

Comment

In the present work, as part of a study of the substituent effects on the solid state structures of benzanilides (Gowda, Foro et al., 2008, 2009; Gowda, Tokarčík et al., 2008), the structure of N-(4-chlorophenyl)3-methylbenzamide (I) has been determined. In the structure, the conformations of the N—H and C=O bonds are anti to each other (Fig. 1), similar to those observed in N-(4-chlorophenyl)2-methylbenzamide (II)(Gowda, Foro et al., 2008), N-(4-chlorophenyl)benzamide (III)(Gowda, Tokarčík et al., 2008), 3-methyl-N-(phenyl)benzamide (IV) (Gowda, Foro et al., 2008) and the parent benzanilide (Bowes et al., 2003). Further, the conformation of the C=O bond in (I) is syn to the meta-methyl substituent in the benzoyl ring. The central amido group –NH—C(=O)– makes a dihedral angle of 32.4 (1)° with the methyl-phenyl ring (benzoyl) and 36.1 (1)° with the chloro-phenyl ring (anilino). The dihedral angle between the two benzene rings is 68.4 (1)°, compared to the values of 83.1 (1)° in (II), 60.76 (3)°) in (III), and 22.17 (18)° & 75.86 (12)°, respectively, in molecules 1 and 2 of (IV).

The packing diagram of molecules in (I) showing the intermolecular N–H···O hydrogen bonds (Table 1) involved in the formation of molecular chains running along the a-axis is shown in Fig. 2.

Experimental

The title compound was prepared according to the literature method (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. Single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of its ethanolic solution at room temperature.