(IUCr) 2,4-Dichloro-N-cyclohexylbenzamide

Volume 64
Part 5
Page o773
May 2008

Received 22 March 2008
Accepted 26 March 2008
Online 2 April 2008

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.111
Data-to-parameter ratio = 20.4
Details

2,4-Dichloro-N-cyclohexylbenzamide

Aamer Saeed,^a ^* Naeem Abbas,^a Shahid Hussain ^a and Ulrich Flörke ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and ^bDepartment für Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
Correspondence e-mail: aamersaeed@yahoo.com

In the title molecule, C₁₃H₁₅Cl₂NO, the cyclohexane ring adopts a chair conformation. The aromatic ring plane is oriented with respect to the N/O/C plane at a dihedral angle of 51.88 (7)°. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules into infinite chains along the [010] direction.

Related literature

For related literature, see: Makino et al. (2001, 2003); Ho et al. (2002); Zhichkin et al. (2007); Jackson et al. (1994); Capdeville et al. (2002); Manley et al. (2002); Igawa et al. (1999); Jones & Kus (2004). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₃H₁₅Cl₂NO
M_r = 272.16
Monoclinic, C 2/c
a = 26.135 (3) Å
b = 4.9144 (6) Å
c = 20.449 (2) Å
= 90.167 (3)°
V = 2626.4 (5) Å³
Z = 8
Mo K radiation
= 0.48 mm^-1
T = 120 (2) K
0.48 × 0.17 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.803, T_max = 0.945
10950 measured reflections
3141 independent reflections
2389 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.110
S = 1.02
3141 reflections
154 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1BO1ⁱ	0.88	1.95	2.796 (3)	161
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2439 ).

Acknowledgements

AS gratefully acknowledges a research grant from Quaid-i-Azam University, Islamabad.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Capdeville, R., Buchdunger, E., Zimmermann, J. & Matter, J. (2002). Nat. Rev. Drug. Discov. 1, 493-502.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Ho, T.-I., Chen, W.-S., Hsu, C.-W., Tsai, Y.-M. & Fang, J.-M. (2002). Heterocycles, 57, 1501-1506.
Igawa, H., Nishimura, M., Okada, K. & Nakamura, T. (1999). Jpn Kokai Tokkyo Koho JP 11171848.
Jackson, S., Degrado, W., Dwivedi, A., Parthasarathy, A., Higley, A., Krywko, J., Rockwell, A., Markwalder, J., Wells, G., Wexler, R., Mousa, S. & Harlow, R. (1994). J. Am. Chem. Soc. 116, 3220-3230.
Jones, P. G. & Kus, P. (2004). Acta Cryst. E60, o1299-o1300.
Makino, S., Nakanishi, E. & Tsuji, T. (2003). Bull. Korean Chem. Soc. 24, 389-392.
Makino, S., Suzuki, N., Nakanishi, E. & Tsuji, T. (2001). Synlett, pp. 333-336.
Manley, P. W., Furet, P., Bold, G., Brüggen, J., Mestan, J., Meyer, T., Schnell, C. R., Wood, J., Haberey, M., Huth, A., Krüger, M., Menrad, A., Ottow, E., Seidelmann, D., Siemeister, G. & Thierauch, K.-H. (2002). J. Med. Chem. 45, 5687-5693.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhichkin, P., Kesicki, E., Treiberg, J., Bourdon, L. M., Ronsheim, M., Ooi, H. C., White, S., Judkins, A. & Fairfax, D. (2007). Org. Lett. 9, 1415-1418.

organic compounds