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Volume 70 
Part 1 
Page o99  
January 2014  

Received 8 December 2013
Accepted 18 December 2013
Online 24 December 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.061
wR = 0.164
Data-to-parameter ratio = 12.8
Details
Open access

(E)-N'-(2-Chloro­benzyl­idene)-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide

aDepartment of Chemistry, Changzhi University, Changzhi, Shanxi 046011, People's Republic of China
Correspondence e-mail: jlwangczu@163.com

In the title compound, C13H11ClN4O3, the phenyl and pyrrolyl ring are linked by an ac­yl-hydrazone (R2C=N-N-CO-R) group, forming a slightly bent mol­ecule: the dihedral angle subtended by the the phenyl and pyrrolyl rings is 8.46 (12)°. In the crystal, the three-dimensional supra­molecular structure is assembled by N-H...O hydrogen bonding. Mol­ecular sheets are formed parallel to (101) in a herringbone arrangement by weak van der Waals inter­actions; weak [pi]-[pi] [centroid-centroid phen­yl-phenyl and pyrrol­yl-pyrrolyl distances of 3.7816 (3) and 3.8946 (2) Å, respectively] inter­actions occur between neighbouring sheets.

Related literature

For applications and structures of aroylhydrazones, see: Raja et al. (2012[Raja, D. S., Bhuvanesh, N. S. P. & Natarajan, K. (2012). Dalton Trans. 41, 4365-4377.]); Wang et al. (2014[Wang, J., Zhao, Y. & Yang, B. (2014). Inorg. Chim. Acta, 409, 484-496.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11ClN4O3

  • Mr = 306.71

  • Monoclinic, P 21 /c

  • a = 13.7649 (13) Å

  • b = 12.4993 (11) Å

  • c = 8.1263 (10) Å

  • [beta] = 95.523 (1)°

  • V = 1391.7 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 298 K

  • 0.30 × 0.20 × 0.16 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.918, Tmax = 0.955

  • 6871 measured reflections

  • 2452 independent reflections

  • 1435 reflections with I > 2[sigma](I)

  • Rint = 0.071

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.164

  • S = 1.00

  • 2452 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...O1i 0.86 2.14 2.941 (3) 154
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and 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.]) and SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2124 ).


Acknowledgements

This work was supported by the National-level College Students' Innovative Training Plan Program of the People's Republic of China (grant No. 201310122001) and the Scientific Research Foundation for PhDs of Changzhi University.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Raja, D. S., Bhuvanesh, N. S. P. & Natarajan, K. (2012). Dalton Trans. 41, 4365-4377.  [CrossRef] [ChemPort] [PubMed]
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]
Wang, J., Zhao, Y. & Yang, B. (2014). Inorg. Chim. Acta, 409, 484-496.  [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o99  [ doi:10.1107/S1600536813034119 ]

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