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Volume 68 
Part 11 
Page o3161  
November 2012  

Received 28 September 2012
Accepted 30 September 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.062
wR = 0.132
Data-to-parameter ratio = 14.1
Details
Open access

N-(2-Phenoxyphenyl)pyrazine-2-carboxamide

aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran, 1983963113, Iran
Correspondence e-mail: mehri.noroozi@gmail.com

In the title compound, C17H13N3O2, the pyrazine ring is oriented at 1.65 (11) and 88.33 (17)° with respect to the benzene rings. The benzene rings are nearly perpendicular to each other [dihedral angle 87.14 (17)°]. In the crystal, a weak C-H...N hydrogen bond occurs.

Related literature

For related structures, see: Wardell et al. (2008[Wardell, S. M. S. V., de Souza, M. V. N., Vasconcelos, T. R. A., Ferreira, M. L., Wardell, J. L., Low, J. N. & Glidewell, C. (2008). Acta Cryst. B64, 84-100.]); de Lima Ferreira et al. (2010[Lima Ferreira, M. de, Souza, M. V. N. de, Wardell, S. M. S. V., Wardell, J. L. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2722-o2723.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13N3O2

  • Mr = 291.30

  • Triclinic, [P \overline 1]

  • a = 5.0913 (10) Å

  • b = 11.769 (2) Å

  • c = 12.268 (3) Å

  • [alpha] = 91.058 (16)°

  • [beta] = 94.541 (16)°

  • [gamma] = 101.648 (15)°

  • V = 717.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.40 × 0.20 × 0.15 mm

Data collection
  • Stoe IPDS II diffractometer

  • 5966 measured reflections

  • 2811 independent reflections

  • 1923 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.132

  • S = 1.07

  • 2811 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...N2i 0.93 2.62 3.439 (3) 147
Symmetry code: (i) -x+3, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5626 ).


Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Lima Ferreira, M. de, Souza, M. V. N. de, Wardell, S. M. S. V., Wardell, J. L. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2722-o2723.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stoe & Cie (2005). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.
Wardell, S. M. S. V., de Souza, M. V. N., Vasconcelos, T. R. A., Ferreira, M. L., Wardell, J. L., Low, J. N. & Glidewell, C. (2008). Acta Cryst. B64, 84-100.  [ISI] [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3161  [ doi:10.1107/S1600536812041050 ]

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