4-Methyl-N-(4-methyl­phen­yl)benzamide

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Chaithanya, U.; Fuess, H.

doi:10.1107/S1600536809006497

Volume 65
Part 3
Page o630
March 2009

Received 21 February 2009
Accepted 23 February 2009
Online 28 February 2009

Key indicators
Single-crystal X-ray study
T = 295 K
Mean () = 0.000 Å
Disorder in main residue
R = 0.037
wR = 0.103
Data-to-parameter ratio = 8.0
Details

4-Methyl-N-(4-methylphenyl)benzamide

B. Thimme Gowda,^a ^* Miroslav Tokarcík,^b Jozef Kozísek,^b U. Chaithanya ^a and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India,^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

In the title compound, C₁₅H₁₅NO, the amide fragment has an anti conformation. The central amide group is tilted with respect to the benzoyl ring, forming a dihedral angle of 32.3 (5)°. The benzoyl and aniline rings make a dihedral angle of 59.6 (5)°. Molecules are linked into infinite supramolecular chains via N-HO hydrogen bonds. The molecule is disordered so that the aromatic rings are disposed across a twofold axis with equal occupancies.

Related literature

For background to our study of the substituent effects on the structures of benzanilides, see: Gowda et al. (2003). For related structures, see Gowda et al. (2008a,b, 2009).

Experimental

Crystal data

C₁₅H₁₅NO
M_r = 225.28
Monoclinic, C 2/c
a = 13.3236 (5) Å
b = 5.3591 (2) Å
c = 17.3525 (6) Å
= 92.248 (3)°
V = 1238.06 (8) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 295 K
0.26 × 0.25 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.984, T_max = 0.995
8166 measured reflections
1235 independent reflections
775 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.103
S = 0.99
1235 reflections
154 parameters
59 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.12 e Å^-3
_min = -0.12 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.883 (15)	2.416 (19)	3.202 (3)	148.3 (6)
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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, 2009) and WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2377 ).

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

Brandenburg, K. (2002). DIAMOND. Crystal Impact, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2009). Z. Naturforsch. Teil A. In preparation. CCDC deposition No. 691312, CCDC, Cambridge, England.
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. (2008a). Acta Cryst. E64, o83.
Gowda, B. T., Tokarcík, M., Kozísek, J., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o1494.
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds