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Volume 69 
Part 11 
Page o1635  
November 2013  

Received 6 October 2013
Accepted 6 October 2013
Online 12 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.029
wR = 0.075
Data-to-parameter ratio = 14.8
Details
Open access

N'-[(E)-3-Bromo­benzyl­idene]pyrazine-2-carbohydrazide

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan,bMedicinal Botanic Centre, PCSIR Laboratories Complex, Peshawar, Pakistan,cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and dDepartment of Chemistry, Kohat University of Science and Technology, Kohat, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C12H9BrN4O, the dihedral angle between the aromatic rings is 12.16 (12)°. An intra­molecular N-H...N hydrogen bond closes an S(5) ring. In the crystal, C-H...O hydrogen bonds link the mol­ecules into C(6) chains propagating in [010]. Very weak aromatic [pi]-[pi] stacking [centroid-centroid separations = 3.9189 (15) and 3.9357 (15) Å] is also observed.

Related literature

For related structures, see: Hameed et al. (2013a[Hameed, S., Ahmad, M., Tahir, M. N., Israr, M. & Anwar, M. (2013a). Acta Cryst. E69, o1419.],b[Hameed, S., Ahmad, M., Tahir, M. N., Shah, M. A. & Shad, H. A. (2013b). Acta Cryst. E69, o1141.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9BrN4O

  • Mr = 305.14

  • Monoclinic, C 2/c

  • a = 14.4115 (8) Å

  • b = 6.2128 (3) Å

  • c = 27.5992 (15) Å

  • [beta] = 104.379 (2)°

  • V = 2393.7 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.43 mm-1

  • T = 296 K

  • 0.34 × 0.25 × 0.23 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.389, Tmax = 0.506

  • 9373 measured reflections

  • 2415 independent reflections

  • 1670 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.075

  • S = 1.02

  • 2415 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...N2 0.86 2.24 2.646 (3) 109
C6-H6...O1i 0.93 2.26 3.150 (3) 160
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7147 ).


Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors are also thankful to the Higher Education Commission (HEC) of Pakistan for financial support. M. Ahmad is thankful to the Pakistan Council of Scientific and Industrial Research (PCSIR) Laboratories of Pakistan for financial support throughout his study leave.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hameed, S., Ahmad, M., Tahir, M. N., Israr, M. & Anwar, M. (2013a). Acta Cryst. E69, o1419.  [CSD] [CrossRef] [IUCr Journals]
Hameed, S., Ahmad, M., Tahir, M. N., Shah, M. A. & Shad, H. A. (2013b). Acta Cryst. E69, o1141.  [CSD] [CrossRef] [IUCr Journals]
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]


Acta Cryst (2013). E69, o1635  [ doi:10.1107/S1600536813027426 ]

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