N-(3-Chloro­phen­yl)-2-methyl­benzamide

B Thimme Gowda; Sabine Foro; B P Sowmya; Hartmut Fuess

doi:10.1107/S1600536808010143

. 2008 Apr 16;64(Pt 5):o861. doi: 10.1107/S1600536808010143

N-(3-Chlorophenyl)-2-methylbenzamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, B P Sowmya ^a, Hartmut Fuess ^b

PMCID: PMC2961145 PMID: 21202348

Abstract

The conformation of the N—H bond in the structure of the title compound, C₁₄H₁₂ClNO, is anti to the meta-chloro substituent in the aniline ring, while the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring. The conformations of the N—H and C=O bonds are anti to each other, similar to those observed in 2-methyl-N-(3-methylphenyl)benzamide (N3MP2MBA). The –NHC(=O)– group makes a dihedral angle of 55.8 (7)° with the benzoyl ring, while the angle between the benzoyl and aniline rings is 37.5 (1)°; the respective values for N3MP2MBA are 55.2 (7) and 36.2 (1)°. N—H⋯O hydrogen bonds link the molecules into infinite chains running along the c axis.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO
M _r = 245.70
Tetragonal,
a = 8.8237 (8) Å
c = 15.977 (2) Å
V = 1243.9 (2) Å³
Z = 4
Cu Kα radiation
μ = 2.57 mm⁻¹
T = 299 (2) K
0.60 × 0.10 × 0.07 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.308, T _max = 0.841
4144 measured reflections
2173 independent reflections
1844 reflections with I > 2σ(I)
R _int = 0.036
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.120
S = 1.07
2173 reflections
159 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ▶), 1020 Friedel pairs
Flack parameter: 0.00 (2)

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010143/om2228sup1.cif

e-64-0o861-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010143/om2228Isup2.hkl

e-64-0o861-Isup2.hkl^{(106.8KB, 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	0.83 (4)	2.12 (4)	2.900 (3)	157 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

In the present work, the structure of 2-methyl-N-(3-chlorophenyl)- benzamide (N3CP2MBA) has been determined as part of substituent effect studies on the solid state structures of benzanilides (Gowda et al., 2003; Gowda et al. (2008a, 2008b). The conformation of the N—H bond in N3CP2MBA (Fig. 1) is anti to the meta-chloro substituent in the aniline ring, while the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring and the conformations of the N—H and C=O bonds are anti to each other, identical to that observed in 2-methyl-N-(3-methylphenyl)-benzamide (N3MP2MBA). The bond parameters in N3CP2MBA are similar to those in 2-methyl-N-(phenyl)-benzamide (Gowda et al., 2008a), N3MP2MBA (Gowda et al., 2008b) and other benzanilides (Gowda et al., 2003). The amide group, –NHCO– makes a dihedral angle of 55.8 (7)° with the benzoyl ring, while that between benzoyl and aniline rings is 37.5 (1)°, compared to the respective values of 55.2 (7)° and 36.2 (1)° for N3MP2MBA. The packing diagram of N3CP2MBA showing the hydrogen bonds N1—H1N···O1 (Table 1) is given 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 were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.