N-(3-Chloro­phen­yl)-3-methyl­benzamide hemihydrate

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

doi:10.1107/S1600536810010354

. 2010 Mar 31;66(Pt 4):o997. doi: 10.1107/S1600536810010354

N-(3-Chlorophenyl)-3-methylbenzamide hemihydrate

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

PMCID: PMC2984021 PMID: 21580793

Abstract

In the title compound, C₁₄H₁₂ClNO·0.5H₂O, the N—H bond is in an anti conformation to the C=O bond. The two aromatic rings make a dihedral angle of 49.5 (1)°. The water molecule lies on a twofold rotation axis. In the crystal, intermolecular N—H⋯O and O—H⋯O hydrogen bonds connect the molecules into a three-dimensional network.

Related literature

For the preparation of the title compound and related structures, see: Gowda et al. (2008a ▶,b ▶); Bowes et al. (2003 ▶); Rodrigues et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO·0.5H₂O
M _r = 254.71
Monoclinic,
a = 7.6497 (3) Å
b = 12.6829 (5) Å
c = 25.9694 (10) Å
β = 95.365 (3)°
V = 2508.54 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 295 K
0.52 × 0.16 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.860, T _max = 0.984
19774 measured reflections
2277 independent reflections
1894 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.095
S = 1.07
2277 reflections
164 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, global. DOI: 10.1107/S1600536810010354/bt5221sup1.cif

e-66-0o997-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010354/bt5221Isup2.hkl

e-66-0o997-Isup2.hkl^{(109.7KB, 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⋯O2Wⁱ	0.86	2.2	3.0155 (19)	158
O2W—H2W⋯O1	0.813 (18)	1.991 (18)	2.7984 (17)	171.9 (19)

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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 the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship.

supplementary crystallographic information

Comment

In the present work, as part of a study of the substituent effects on the crystal structures of benzanilides (Gowda et al., 2008a,b, Rodrigues et al., 2010), the structure of N-(3-chlorophenyl)3-methylbenzamide hydrate (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-(3-chlorophenyl)3-chlorobenzamide (II), N-(3-chlorophenyl)benzamide (III)(Gowda et al., 2008b), 3-methyl-N-(phenyl)benzamide (IV)(Gowda et al., 2008a), N-(2-chlorophenyl)3-methylbenzamide (V)(Rodrigues et al., 2010) and the parent benzanilide (Bowes et al., 2003). Further, the conformation of the C=O bond in (I) is also anti to the meta- methyl substituent in the benzoyl ring and that of the N—H bond is anti to the meta-Cl group in the aniline ring, compared to the syn conformation observed between the N—H bond and the ortho-Cl group in the aniline ring of (V).

The two aromatic rings make a dihedral angle of 49.5 (1)°. The central amide group –NH–C(=O)– is twisted by 35.1 (1)° and 15.9 (1)° out of the planes of the 3-methylphenyl and 3-chlorophenyl ring, respectively. The molecular structure is stabilized by the C9–H9···O1 intramolecular hydrogen bond (Table 1). In the crystal, the water molecule lies on a twofold rotation axis.

Intermolecular N–H···O and O–H···O hydrogen bonds connect the molecules into a three-dimensional network (Fig.2). The water O2w oxygen lies on a twofold rotation axis 0,y,1/4 and its hydrogen atoms are related by the symmetry -x, y, 1/2 - z.

Experimental

The title compound was prepared according to the literature method (Gowda et al., 2008a,b). 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 in the presence of a few drops of water, at room temperature.