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Volume 69 
Part 1 
Page o129  
January 2013  

Received 12 December 2012
Accepted 15 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
H completeness 95%
R = 0.033
wR = 0.083
Data-to-parameter ratio = 12.5
Details
Open access

2-[4-(Morpholin-4-ylmethyl)phenyl]benzonitrile

aDepartment of Studies in Chemistry, Karnataka University, Dharwad 580 003, Karnataka, India, and bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com, kamchem9@gmail.com

In the title compound, C18H18N2O, the morpholine ring adopts a chair conformation with the exocyclic N-C bond in an equatorial orientation. The dihedral angles between the central benzene ring and the morpholine ring (all atoms) and the cyanobenzene ring are 87.87 (7) and 52.54 (7)°, respectively. No significant intermolecular interactions are observed in the crystal structure.

Related literature

For biological applications of biphenyl derivatives see; Li et al. (2011[Li, W., Xu, Z., Sun, P., Jiang, X. & Fang, M. (2011). Org. Lett. 13, 1286-1289.]); Hadizad et al. (2009[Hadizad, T., Kirkpatrick, A. S., Mason, S., Burns, K., Beanlands, R. S. & Dasilva, J. N. (2009). Bioorg. Med. Chem. 23, 7971-7977.]); Larsen et al. (1994[Larsen, R. D., King, A. O., Chen, C. Y., Corley, E. G., Foster, B. S., Roberts, F. E., Yang, C., Lieberman, D. R. & Reamer, R. A. (1994). J. Org. Chem. 59, 6391-6394.]); Kamble et al. (2011[Kamble, R. R., Biradar, D. B., Meti, G. Y., Tasneem, T., Tegginamath, G., Khazi, I. M., Vaidynathan, S. T., Mohandoss, R. & Balasubramanian, S. V. P. (2011). J. Chem. Sci. 123, 393-401.]); Zhang et al. (2004[Zhang, H., Yang, B., Zheng, Y., Yang, G., Ye, L., Ma, Y., Chen, X., Cheng, G. & Liu, S. (2004). J. Phys. Chem. B, 108, 9571-9573.]); Chan et al. (1994[Chan, W., Butler, R. G. & Smith, R. G. (1994). J. Med. Chem. 37, 897-906.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18N2O

  • Mr = 278.34

  • Monoclinic, P 21 /c

  • a = 21.1079 (5) Å

  • b = 8.1358 (1) Å

  • c = 9.0793 (2) Å

  • [beta] = 100.833 (1)°

  • V = 1531.40 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.770, Tmax = 1.000

  • 10319 measured reflections

  • 2387 independent reflections

  • 1948 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.083

  • S = 1.03

  • 2387 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.10 e Å-3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7014 ).


Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the data collection. The authors are also grateful to University Grants Commission, New Delhi for financial assistance [letter No. 37-248/2009 (SR)].

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chan, W., Butler, R. G. & Smith, R. G. (1994). J. Med. Chem. 37, 897-906.  [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hadizad, T., Kirkpatrick, A. S., Mason, S., Burns, K., Beanlands, R. S. & Dasilva, J. N. (2009). Bioorg. Med. Chem. 23, 7971-7977.  [CrossRef]
Kamble, R. R., Biradar, D. B., Meti, G. Y., Tasneem, T., Tegginamath, G., Khazi, I. M., Vaidynathan, S. T., Mohandoss, R. & Balasubramanian, S. V. P. (2011). J. Chem. Sci. 123, 393-401.  [CrossRef] [ChemPort]
Larsen, R. D., King, A. O., Chen, C. Y., Corley, E. G., Foster, B. S., Roberts, F. E., Yang, C., Lieberman, D. R. & Reamer, R. A. (1994). J. Org. Chem. 59, 6391-6394.  [CrossRef] [ChemPort]
Li, W., Xu, Z., Sun, P., Jiang, X. & Fang, M. (2011). Org. Lett. 13, 1286-1289.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhang, H., Yang, B., Zheng, Y., Yang, G., Ye, L., Ma, Y., Chen, X., Cheng, G. & Liu, S. (2004). J. Phys. Chem. B, 108, 9571-9573.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o129  [ doi:10.1107/S1600536812050957 ]

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