N-(4-Chloro­phen­yl)-4-meth­oxy­benzamide

Kant, R.; Sahi, S.; Gupta, V.K.; Kapoor, K.; Paul, S.

doi:10.1107/S1600536812041384

Volume 68
Part 11
Page o3077
November 2012

Received 28 September 2012
Accepted 2 October 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.100
Data-to-parameter ratio = 14.3
Details

N-(4-Chlorophenyl)-4-methoxybenzamide

Rajni Kant,^a ^* Seema Sahi,^b Vivek K. Gupta,^a Kamini Kapoor ^a and Satya Paul ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bPost-Graduate Department of Chemistry, University of Jammu, Jammu Tawi 180 006, India
Correspondence e-mail: rkvk.paper11@gmail.com

In the title compound, C₁₄H₁₂ClNO₂, the mean plane through the amide group [-N-C=O-] forms dihedral angles of 27.55 (8) and 31.94 (7)° with the methoxy- and chloro-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 59.24 (4)°. In the crystal, N-HO and weak C-HO hydrogen bonds link the molecules into chains along the a axis.

Related literature

For the biological activity of amides, see: Chen et al. (2011); El Rayes et al. (2008); Regiec et al. (2006); Kuroda et al. (2006). For related structures, see: Gowda et al. (2008); Saeed et al. (2008).

Experimental

Crystal data

C₁₄H₁₂ClNO₂
M_r = 261.70
Triclinic, $[P \overline 1]$
a = 5.4394 (2) Å
b = 7.7754 (3) Å
c = 14.9262 (6) Å
= 78.759 (3)°
= 80.712 (3)°
= 88.821 (3)°
V = 611.01 (4) Å³
Z = 2
Mo K radiation
= 0.31 mm^-1
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.952, T_max = 1.000
14438 measured reflections
2407 independent reflections
1997 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.100
S = 1.03
2407 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.17 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.83 (4)	2.47 (2)	3.222 (2)	151 (2)
C14-H14O1ⁱ	0.93	2.56	3.251 (2)	131
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5539 ).

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

Chen, Q., Ilies, L., Yoshikai, N. & Nakamura, E. (2011). Org. Lett. 13, 3232-3234.
El Rayes, S. M., Ali, I. A. I. & Walid, F. (2008). Arkivoc, XI, 86-95.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1421.
Kuroda, N., Hird, N. & Cork, D. G. (2006). J. Comb. Chem. 8, 505-512.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Regiec, A., Machon, Z., Miedzybrodzki, R. & Szymaniec, S. (2006). Arch. Pharm. Chem. Life Sci. 339, 401-413.
Saeed, A., Khera, R. A., Gotoh, K. & Ishida, H. (2008). Acta Cryst. E64, o1934.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds