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Volume 69 
Part 9 
Page o1419  
September 2013  

Received 7 August 2013
Accepted 7 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.138
Data-to-parameter ratio = 13.4
Details
Open access

N'-[(E)-1-(2-Hydroxyphenyl)ethylidene]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

The title compound, C13H12N4O2, crystallized with two independent molecules (A and B) in the asymmetric unit. Molecule B is planar to within 0.044 (3) Å for all non-H atoms, while molecule A is slightly twisted, with a dihedral angle of 6.29 (4)° between the mean planes of the pyrazine-2-carbohydrazide and 1-(2-hydroxyphenyl)ethanone moieties (r.m.s. deviations = 0.0348 and 0.0428 Å, respectively). S(5) and S(6) ring motifs are formed in both molecules due to the presence of intramolecular O-H...N and N-H...N hydrogen bonds. In the crystal, molecules A and B are linked by a C-H...O hydrogen bond. They stack along the a-axis direction, forming columns with [pi]-[pi] interactions involving inversion-related pyrazine and benzene rings [centroid-centroid distances = 3.5489 (13)-3.8513 (16) Å].

Related literature

For a related crystal structure and other studies, see: Hameed et al. (2013[Hameed, S., Ahmad, M., Tahir, M. N., Shah, M. A. & Shad, H. A. (2013). Acta Cryst. E69, o1141.]). 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
  • C13H12N4O2

  • Mr = 256.27

  • Triclinic, [P \overline 1]

  • a = 7.1767 (7) Å

  • b = 10.1743 (10) Å

  • c = 17.1150 (17) Å

  • [alpha] = 86.172 (3)°

  • [beta] = 85.275 (2)°

  • [gamma] = 80.963 (4)°

  • V = 1228.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.28 × 0.23 × 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 = 0.973, Tmax = 0.981

  • 19042 measured reflections

  • 4821 independent reflections

  • 2608 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.138

  • S = 1.00

  • 4821 reflections

  • 361 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.23 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
O1-H1...N1 0.82 1.82 2.537 (2) 145
N2-H2A...N3 0.80 (2) 2.26 (2) 2.654 (3) 111.5 (17)
O3-H3A...N5 0.82 1.82 2.534 (3) 145
N6-H6...N7 0.80 (3) 2.21 (3) 2.628 (3) 113 (3)
C3-H3...O3i 0.93 2.59 3.403 (3) 146
Symmetry code: (i) -x+1, -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 (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: SU2634 ).


Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan, and also thank the Higher Education Commission (HEC) of Pakistan for financial support. MA is grateful to the Pakistan Council of Scientific and Industrial Research (PCSIR) Laboratories of Pakistan for financial support through out 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] [ISI]
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.  [ISI] [CrossRef] [ChemPort] [details]
Hameed, S., Ahmad, M., Tahir, M. N., Shah, M. A. & Shad, H. A. (2013). Acta Cryst. E69, o1141.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1419  [ doi:10.1107/S1600536813022137 ]

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