(E)-4-Amino-N′-(3-nitro­benzyl­idene)benzohydrazide

Xu, S.-Q.

doi:10.1107/S1600536812014110

Volume 68
Part 5
Page o1320
May 2012

Received 30 March 2012
Accepted 31 March 2012
Online 6 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.057
wR = 0.161
Data-to-parameter ratio = 15.5
Details

(E)-4-Amino-N'-(3-nitrobenzylidene)benzohydrazide

Shu-Qing Xu ^a ^*

^aSchool of Ocean, Qinzhou University, Qinzhou, Guangxi 535000, People's Republic of China
Correspondence e-mail: shuqing_xu@163.com

In the title compound, C₁₄H₁₂N₄O₃, the dihedral angle between the benzene rings is 7.6 (4)°. In the crystal, infinite sheets linked by N-HO and bifurcated N-H(O,N) hydrogen bonds propagate in the (10-1) plane, in which R₄⁴(36) loops are apparent. Neighbouring layers may interact by way of very weak [pi] - [pi] stacking interactions [centroid-centroid distances = 3.9329 (13) and 4.0702 (13) Å].

Related literature

For related structures and background references to hydrazones, see: Cao (2009); Zhou & Yang (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₂N₄O₃
M_r = 284.28
Monoclinic, P 2₁ /n
a = 7.8909 (16) Å
b = 11.153 (2) Å
c = 14.709 (3) Å
= 92.00 (3)°
V = 1293.7 (4) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 296 K
0.20 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.981, T_max = 0.987
11091 measured reflections
2952 independent reflections
2756 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.161
S = 1.06
2952 reflections
190 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2N1ⁱ	0.86	2.47	3.183 (2)	141
N2-H2O3ⁱⁱ	0.86	2.44	3.041 (2)	127
N1-H1AO1ⁱⁱⁱ	0.89	2.27	3.106 (2)	156
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6724 ).

Acknowledgements

This work was supported by the Natural Science Foundation of Guangxi Province (grant No. 2011GXNSFA018123). The author also acknowledges financial support from the Natural Science Foundation of Education Bureau of Guangxi Province (grant No. 201106LX537).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl., 34, 1555-1573.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, G.-B. (2009). Acta Cryst. E65, o2415.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhou, C.-S. & Yang, T. (2010). Acta Cryst. E66, o365.

organic compounds