N-(3-Methyl­phen­yl)benzamide

Gowda, B.T.; Foro, S.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808035186

Volume 64
Part 11
Page o2247
November 2008

Received 19 October 2008
Accepted 28 October 2008
Online 31 October 2008

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.009 Å
Disorder in main residue
R = 0.044
wR = 0.129
Data-to-parameter ratio = 6.4
Details

N-(3-Methylphenyl)benzamide

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

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

The asymmetric unit of the title compound, C₁₄H₁₃NO, contains four molecules, which are linked through N-HO hydrogen bonds into two symmetry-independent chains running parallel to [001] and [101]. The N-H and C=O bonds of the amide groups are trans oriented in all four molecules. The molecules are not planar and both aromatic rings are twisted strongly relative to the plane of the amide group. The dihedral angle between the two benzene rings ranges from 70.6 (2) to 74.2 (2)°. The N-H bond is anti to the meta-methyl substituent in the aniline fragment in three of the four symmetry-independent molecules. In the fourth molecule, the aniline unit is disordered over two nearly coplanar positions; the anti and syn conformers occupy the same site in the crystal with equal probability.

Related literature

For the general procedure for the synthesis of the title compound, see: Gowda et al. (2003). For structure of the 3-chlorophenyl analogue, see: Gowda et al. (2008).

Experimental

Crystal data

C₁₄H₁₃NO
M_r = 211.25
Monoclinic, C c
a = 13.269 (2) Å
b = 53.686 (6) Å
c = 9.3921 (12) Å
= 134.21 (1)°
V = 4795.7 (10) Å³
Z = 16
Cu K radiation
= 0.58 mm^-1
T = 299 (2) K
0.43 × 0.25 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
9315 measured reflections
4168 independent reflections
3197 reflections with I > 2(I)
R_int = 0.028
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.129
S = 1.03
4168 reflections
653 parameters
110 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.87 (3)	1.96 (3)	2.822 (4)	168 (4)
N2-H2NO1	0.84 (3)	2.06 (3)	2.848 (4)	156 (5)
N3-H3NO4ⁱⁱ	0.86 (3)	2.00 (3)	2.829 (4)	163 (4)
N4-H4NO3ⁱ	0.82 (3)	2.04 (3)	2.813 (4)	156 (5)
Symmetry codes: (i) x-1, y, z-1; (ii) x+1, y, z.

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) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2174 ).

Acknowledgements

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

References

Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225-230.
Gowda, B. T., Tokarcík, M., Kozísek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o462.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds