2-Methyl-N-p-tolyl­benzamide: a second monoclinic polymorph

Saeed, A.; Khera, R.A.; Simpson, J.

doi:10.1107/S1600536810010378

Volume 66
Part 4
Pages o911-o912
April 2010

Received 18 March 2010
Accepted 19 March 2010
Online 24 March 2010

Key indicators
Single-crystal X-ray study
T = 89 K
Mean (C-C) = 0.004 Å
R = 0.040
wR = 0.108
Data-to-parameter ratio = 8.1
Details

2-Methyl-N-p-tolylbenzamide: a second monoclinic polymorph

Aamer Saeed,^a ^* Rasheed Ahmad Khera ^a and Jim Simpson ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
Correspondence e-mail: aamersaeed@yahoo.com

The title compound, C₁₅H₁₅NO, (I), is a polymorph of the structure (II) reported by Gowda et al. [Acta Cryst. (2008), E64, o1494]. Compound (II) crystalllizes in the space group C2/c (Z = 8), whereas the title compound occurs in space group P2₁/c (Z = 4). The two molecular structures differ slightly in the relative orientations of their central amide group with respect to the benzoyl ring [dihedral angles of 55.99 (7) for (I) and 59.96 (11)° for (II)] and in the inclination of the benzoyl and aniline rings [88.67 (8) for (I) and 81.44 (5)° for (II)]. In the crystal structure of (I), molecules are linked by N-HO hydrogen bonds, forming C(4) chains, which are augmented by weak C-HO interactions. The structure is further stabilized by C-H [pi] contacts involving both of the aromatic rings.

Related literature

For the biological activity of N-substituted benzamides, see: Olsson et al. (2002); Lindgren et al. (2001). For the use of heterocyclic analogs of benzanilide derivatives as potassium channel activators, see: Calderone et al. (2006). For the use of 2-nitrobenzamides in organic synthesis, see: Zhichkin et al. (2007); Beccalli et al. (2005). For the original monoclinic polymorph, see: Gowda et al. (2008). For the related N-(2,4-dimethylphenyl)-2-methylbenzamide, see: Gowda et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₅H₁₅NO
M_r = 225.28
Monoclinic, P 2₁ /c
a = 20.259 (3) Å
b = 7.0681 (10) Å
c = 8.7941 (13) Å
= 95.942 (9)°
V = 1252.5 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 89 K
0.30 × 0.19 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006) T_min = 0.803, T_max = 1.000
8447 measured reflections
1283 independent reflections
1028 reflections with I > 2(I)
R_int = 0.052
_max = 20.7°

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.108
S = 1.07
1283 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3-C7 and C8-C13 benzene rings, repectively.

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.90 (3)	1.94 (3)	2.821 (3)	169 (2)
C9-H9O1ⁱ	0.95	2.71	3.366 (3)	127
C7-H7Cg2ⁱⁱ	0.95	2.84	3.751 (3)	160
C31-H31CCg1ⁱⁱⁱ	0.98	2.86	3.676 (3)	141
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 and SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5364 ).

Acknowledgements

The authors gratefully acknowledge a research grant from the Higher Education Commission of Pakistan, project No.20-Miscel/R&D/00/3834. We also thank the University of Otago for the purchase of the diffractometer.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.
Beccalli, E. M., Broggini, G., Paladinoa, G. & Zonia, C. (2005). Tetrahedron, 61, 61-68.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Calderone, V., Fiamingo, F. L., Giorgi, I., Leonardi, M., Livi, O., Martelli, A. & Martinotti, E. (2006). Eur. J. Med. Chem. 41, 761-767.
Gowda, B. T., Tokarcík, M., Kozísek, J., Rodrigues, V. Z. & Fuess, H. (2009). Acta Cryst. E65, o826.
Gowda, B. T., Tokarcík, M., Kozísek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1494.
Hunter, K. A. & Simpson, J. (1999). TITAN2000. University of Otago, New Zealand.
Lindgren, H., Pero, R. W., Ivars, F. & Leanderson, T. (2001). Mol. Immunol. 38, 267-277.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Olsson, A. R., Lindgren, H., Pero, R. W. & Leanderson, T. (2002). Br. J. Cancer, 86, 971-978.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). publCIF. In preparation.
Zhichkin, P., Kesicki, E., Treiberg, J., Bourdon, L., Ronsheim, M., Ooi, H. C., White, S., Judkins, A. & Fairfax, D. (2007). Org. Lett. 9, 1415-1418.

organic compounds