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Volume 69 
Part 12 
Page o1788  
December 2013  

Received 24 October 2013
Accepted 13 November 2013
Online 20 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.135
Data-to-parameter ratio = 13.9
Details
Open access

5-(5'-Fluoro-2'-meth­oxy­biphenyl-3-yl)-1,3,4-oxa­diazol-2-amine

aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and cPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
Correspondence e-mail: dr@physics.uni-mysore.ac.in

In the title compound, C15H12FN3O2, the dihedral angles between the central benzene ring and the pendant benzene and oxa­diazole rings are 45.05 (13) and 15.60 (14)°, respectively. The C atom of the meth­oxy group is roughly coplanar with its attached ring [displacement = 0.178 (4) Å]. In the crystal, N-H...N hydrogen bonds link the mol­ecules into [010] chains. Weak C-H...[pi] inter­actions are also observed.

Related literature

For background to the title compound, see: Ainsworth (1965[Ainsworth, C. (1965). J. Am. Chem. Soc. 87, 5800-5803.]); Paik et al. (2002[Paik, K. L., Baek, N. S., Kim, H. K., Lee, J. H. & Lee, Y. (2002). Macromolecules, 35, 6782-6791.]); Kulkarni et al. (2004[Kulkarni, A. P., Tonzola, C. J., Babel, A. & Jenekhe, S. A. (2004). Chem. Mater. 16, 4556-4573.]). For a related structure, see: Zheng et al. (2012[Zheng, J., Li, W., Song, M. & Xu, Y. (2012). Acta Cryst. E68, o1668.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12FN3O2

  • Mr = 285.28

  • Monoclinic, P 21 /c

  • a = 12.9105 (9) Å

  • b = 6.1738 (4) Å

  • c = 16.9255 (11) Å

  • [beta] = 90.341 (7)°

  • V = 1349.05 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.806, Tmax = 1.000

  • 5027 measured reflections

  • 2650 independent reflections

  • 1382 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.135

  • S = 1.01

  • 2650 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13-C18 ring.

D-H...A D-H H...A D...A D-H...A
N6-H6A...N3i 0.86 2.13 2.972 (3) 166
N6-H6B...N4ii 0.86 2.29 3.118 (3) 161
C17-H17...Cg3iii 0.93 2.72 3.53 146
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x, y+1, z; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis RED and 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[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.]); 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: HB7155 ).


Acknowledgements

RK acknowledges the DST, New Delhi, for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. MKU thanks the DST, New Delhi, for the award of an INSPIRE Fellowship. VKG is thankful to the University of Jammu, Jammu, India, for financial support. DR acknowledges the UGC, New Delhi, for financial support under the Major Research Project- scheme [No. F.41-882/2012 (SR)].

References

Ainsworth, C. (1965). J. Am. Chem. Soc. 87, 5800-5803.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kulkarni, A. P., Tonzola, C. J., Babel, A. & Jenekhe, S. A. (2004). Chem. Mater. 16, 4556-4573.  [Web of Science] [CrossRef] [ChemPort]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Paik, K. L., Baek, N. S., Kim, H. K., Lee, J. H. & Lee, Y. (2002). Macromolecules, 35, 6782-6791.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zheng, J., Li, W., Song, M. & Xu, Y. (2012). Acta Cryst. E68, o1668.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1788  [ doi:10.1107/S1600536813031206 ]

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