4-Chloro-N-(2,6-dimethyl­phen­yl)benzamide

B Thimme Gowda; Miroslav Tokarčík; Jozef Kožíšek; B P Sowmya; Hartmut Fuess

doi:10.1107/S1600536808019120

. 2008 Jun 28;64(Pt 7):o1365. doi: 10.1107/S1600536808019120

4-Chloro-N-(2,6-dimethylphenyl)benzamide

B Thimme Gowda ^a,^*, Miroslav Tokarčík ^b, Jozef Kožíšek ^b, B P Sowmya ^a, Hartmut Fuess ^c

PMCID: PMC2961789 PMID: 21202983

Abstract

The conformations of the N—H and C=O bonds in the structure of the title compound (N26DMP4CBA), C₁₅H₁₄ClNO, are anti to each other, similar to that observed in N-phenylbenzamide, N-(3,4-dimethylphenyl)benzamide, N-(2,6-dichlorophenyl)benzamide and other benzanilides. There are three molecules in the asymmetric unit of N26DMP4CBA. The central amide group is tilted with respect to the benzoyl ring by 45.2 (1)° in molecule 1, 21.2 (2)° in molecule 2 and 14.9 (2)° in molecule 3. The dihedral angles between the benzoyl and aniline rings are 39.9 (1), 51.0 (1) and 86.3 (3)° in molecules 1, 2 and 3, respectively. Intermolecular N—H⋯O hydrogen bonds link the molecules into infinite chains running along the [101] direction. One xylyl group is disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

Related literature

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

Experimental

Crystal data

C₁₅H₁₄ClNO
M _r = 259.72
Triclinic,
a = 12.2696 (3) Å
b = 13.6249 (4) Å
c = 13.7981 (4) Å
α = 91.880 (2)°
β = 113.623 (2)°
γ = 90.3676 (18)°
V = 2111.74 (10) Å³
Z = 6
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 295 (2) K
0.49 × 0.22 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction (2007 ▶); based on Clark & Reid (1995 ▶)] T _min = 0.896, T _max = 0.973
63529 measured reflections
8072 independent reflections
3945 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.137
S = 0.89
8072 reflections
543 parameters
21 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; 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, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019120/dn2356sup1.cif

e-64-o1365-sup1.cif^{(29.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019120/dn2356Isup2.hkl

e-64-o1365-Isup2.hkl^{(386.9KB, 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—H1⋯O2	0.86	2.02	2.8585 (19)	165
N2—H2⋯O3	0.86	1.96	2.778 (2)	158
N3—H3A⋯O1ⁱ	0.86	1.99	2.814 (2)	161

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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 the purchase of the diffractometer.

supplementary crystallographic information

Comment

In the present work, the structure of N-(2,6-dimethylphenyl)- 4-chlorobenzamide (N26DMP4CBA) has been determined to study the effect of substituents on the solid state geometries of benzanilides (Gowda et al., 2003, 2008a,b).

The conformations of the N—H and C=O bonds in N26DMP4CBA (Fig.1) are anti to each other, similar to that observed in N-(phenyl)-benzamide(NPBA)(Gowda et al., 2003), N-(3,4-dimethylphenyl)-benzamide (Gowda et al., 2008a), N-(2,6-dichlorophenyl)-benzamide and other benzanilides (Gowda et al., 2008b), with similar bond parameters. The amide group –NHCO– forms the dihedral angle of 45.2 (1)° in molecule 1, 21.2 (1)° in molecule 2, and 14.9 (2)° in molecule 3, with the benzoyl benzene ring. The dihedral angles between the benzoyl and aniline benzene rings are 39.9 (1)°, 51.0 (1)° and 86.3 (3)° in the molecule 1, 2 and 3, respectively.

The intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the [101] direction (Table 1).

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.