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Volume 69 
Part 7 
Page o1073  
July 2013  

Received 20 May 2013
Accepted 4 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.058
wR = 0.175
Data-to-parameter ratio = 12.6
Details
Open access

4-Nitro-N^2^-(pyridin-4-ylmethylidene)benzene-1,2-diamine

aCollege of Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: guocheng@njut.edu.cn

In the title compound, C12H10N4O2, the dihedral angle between the aromatic rings is 43.18 (16)°. The nitro group is rotated from its attached ring by 7.8 (2)° and a short intramolecular N-H...N contact occurs. In the crystal, the molecules are linked by N-H...N and C-H...O hydrogen bonds, generating a three-dimensional network.

Related literature

For the synthesis, see: Luo et al. (2009[Luo, T. T., Wu, H. C. & Jao, Y. C. (2009). Angew. Chem. 48, 9461-9464.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10N4O2

  • Mr = 242.24

  • Monoclinic, C 2/c

  • a = 21.324 (4) Å

  • b = 9.1480 (18) Å

  • c = 12.950 (3) Å

  • [beta] = 116.36 (3)°

  • V = 2263.5 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.970, Tmax = 0.990

  • 2128 measured reflections

  • 2070 independent reflections

  • 1247 reflections with I > 2[sigma](I)

  • Rint = 0.038

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.175

  • S = 1.01

  • 2070 reflections

  • 164 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...N4i 0.86 2.42 3.091 (3) 135
N2-H2B...N3 0.86 2.42 2.751 (3) 103
C10-H10A...O1ii 0.93 2.49 3.156 (5) 128
Symmetry codes: (i) [-x+1, y+1, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994)[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]; cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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: HB7085 ).


Acknowledgements

The authors thank the Center of Test and Analysis, Nanjing University, for support.

References

Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Luo, T. T., Wu, H. C. & Jao, Y. C. (2009). Angew. Chem. 48, 9461-9464.  [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [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, o1073  [ doi:10.1107/S1600536813015481 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.