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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 [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.100
Data-to-parameter ratio = 14.3
Details
Open access

N-(4-Chlorophenyl)-4-methoxybenzamide

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-H...O and weak C-H...O hydrogen bonds link the molecules into chains along the a axis.

Related literature

For the biological activity of amides, see: Chen et al. (2011[Chen, Q., Ilies, L., Yoshikai, N. & Nakamura, E. (2011). Org. Lett. 13, 3232-3234.]); El Rayes et al. (2008[El Rayes, S. M., Ali, I. A. I. & Walid, F. (2008). Arkivoc, XI, 86-95.]); Regiec et al. (2006[Regiec, A., Machon, Z., Miedzybrodzki, R. & Szymaniec, S. (2006). Arch. Pharm. Chem. Life Sci. 339, 401-413.]); Kuroda et al. (2006[Kuroda, N., Hird, N. & Cork, D. G. (2006). J. Comb. Chem. 8, 505-512.]). For related structures, see: Gowda et al. (2008[Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1421.]); Saeed et al. (2008[Saeed, A., Khera, R. A., Gotoh, K. & Ishida, H. (2008). Acta Cryst. E64, o1934.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO2

  • Mr = 261.70

  • Triclinic, [P \overline 1]

  • a = 5.4394 (2) Å

  • b = 7.7754 (3) Å

  • c = 14.9262 (6) Å

  • [alpha] = 78.759 (3)°

  • [beta] = 80.712 (3)°

  • [gamma] = 88.821 (3)°

  • V = 611.01 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.952, Tmax = 1.000

  • 14438 measured reflections

  • 2407 independent reflections

  • 1997 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.83 (4) 2.47 (2) 3.222 (2) 151 (2)
C14-H14...O1i 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [ChemPort] [PubMed]
El Rayes, S. M., Ali, I. A. I. & Walid, F. (2008). Arkivoc, XI, 86-95.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1421.  [CSD] [CrossRef] [details]
Kuroda, N., Hird, N. & Cork, D. G. (2006). J. Comb. Chem. 8, 505-512.  [ISI] [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [ChemPort]
Saeed, A., Khera, R. A., Gotoh, K. & Ishida, H. (2008). Acta Cryst. E64, o1934.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3077  [ doi:10.1107/S1600536812041384 ]

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