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Volume 69 
Part 7 
Page o1141  
July 2013  

Received 13 June 2013
Accepted 18 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.039
wR = 0.084
Data-to-parameter ratio = 15.5
Details
Open access

N'-[(E)-4-Bromobenzylidene]pyrazine-2-carbohydrazide

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan,bMedicinal Botanic Centre, PCSIR Laboratories Complex, Peshawar, Pakistan,cDepartment of Physics, University of Sargodha, Sargodha, Pakistan,dDepartment of Chemistry, University of Hazara, Mansehra, Pakistan, and eDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C12H9BrN4O, the N'-methylidenepyrazine-2-carbohydrazide and 4-bromobenzene groups are oriented at a dihedral angle of 10.57 (7)°. The hydrazide N-H group is involved in intramolecular N-H...N interaction, which generates an S(5) motif. A short C-H...O interaction is formed between the methylidene H atom and the carbonyl O atom. It connects molecules into chains extending along [100]. In addition, molecules are arranged into stacks extending along [010] via [pi]-[pi] interactions between pyrazine and benzene rings, with centroid-centroid distances of 3.837 (2) and 3.860 (2) Å.

Related literature

For a related crystal structure and related studies, see: Hearn & Cynamon (2004[Hearn, M. J. & Cynamon, M. H. (2004). J. Antimicrob. Chemother. 53, 185-191.]); Jin et al. (2006[Jin, L., Chen, J., Song, B., Chen, Z., Yang, S., Li, Q., Hu, D. & Xu, R. (2006). Bioorg. Med. Chem. Lett. 16, 5036-5040.]); Yuan et al. (2006[Yuan, C.-C., Wu, L., Xing, Z.-Y. & Shi, X.-F. (2006). Acta Cryst. E62, o3274-o3275.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9BrN4O

  • Mr = 305.14

  • Triclinic, [P \overline 1]

  • a = 5.8947 (9) Å

  • b = 7.6941 (12) Å

  • c = 14.029 (2) Å

  • [alpha] = 83.273 (7)°

  • [beta] = 80.086 (7)°

  • [gamma] = 72.440 (6)°

  • V = 596.11 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.44 mm-1

  • T = 296 K

  • 0.26 × 0.22 × 0.20 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 = 0.425, Tmax = 0.503

  • 7382 measured reflections

  • 2529 independent reflections

  • 1403 reflections with I > 2[sigma](I)

  • Rint = 0.074

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.084

  • S = 0.94

  • 2529 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O1i 0.93 2.24 3.132 (4) 161
N3-H3A...N1 0.86 2.27 2.671 (3) 108
Symmetry code: (i) x+1, y, 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: GK2580 ).


Acknowledgements

The authors acknowledge the provision of funds for the purchase of a 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. MA is also thankful to the Pakistan Council of Scientific and Industrial Research (PCSIR) Laboratories of Pakistan for financial support throughout his study leave.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
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]
Hearn, M. J. & Cynamon, M. H. (2004). J. Antimicrob. Chemother. 53, 185-191.  [CrossRef] [PubMed] [ChemPort]
Jin, L., Chen, J., Song, B., Chen, Z., Yang, S., Li, Q., Hu, D. & Xu, R. (2006). Bioorg. Med. Chem. Lett. 16, 5036-5040.  [CSD] [CrossRef] [PubMed] [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]
Yuan, C.-C., Wu, L., Xing, Z.-Y. & Shi, X.-F. (2006). Acta Cryst. E62, o3274-o3275.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1141  [ doi:10.1107/S1600536813016917 ]

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