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Volume 69 
Part 1 
Page o72  
January 2013  

Received 14 September 2012
Accepted 5 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.044
wR = 0.121
Data-to-parameter ratio = 12.5
Details
Open access

(Z)-1-Chloro-1-[2-(2-nitrophenyl)hydrazinylidene]propan-2-one

aChemistry Department, Faculty of Science, Islamic University of Gaza, PO Box 108, Gaza, Palestine,bDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, D-55099 Mainz, Germany, and cManchester Institute of Biotechnology, School of Chemistry and EPS, The University of Manchester, Manchester M1 7DN, England
Correspondence e-mail: john.m.gardiner@manchester.ac.uk

The title molecule, C9H8ClN3O3, lies on a mirror plane. Intramolecular N-H...O and N-H...Cl hydrogen bonds occur. One of the nitro O atoms is disordered (site occupancy ratio = 0.40:0.10).

Related literature

For details of the synthesis and for the importance of hydrazonoyl halides in organic synthesis and their biological activity and metabolism, see: Awadallah et al. (2006[Awadallah, A. M., Seppelt, K. & Shorafa, H. (2006). Tetrahedron, 62, 7744-7746.], 2008[Awadallah, A. & Zahra, J. (2008). Molecules, 13, 170-176.]); Budarina et al. (2007[Budarina, E. V., Dolgushina, T. S., Petrov, M. L., Labeish, N. N., Koltsov, A. A. & Belskii, K. (2007). Russ. J. Org. Chem. 43, 1516-1525.]); Shawalia et al. (2009[Shawalia, A. S. & Samy, N. A. (2009). The Open Bioactive Compd J. 2, 8-16.]); Thaher et al. (2002[Thaher, B. A., Zahra, J. A. & El-Abadelah, M. M. (2002). J. Heterocycl. Chem. 39, 901-904.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8ClN3O3

  • Mr = 241.63

  • Orthorhombic, P n m a

  • a = 14.1344 (10) Å

  • b = 6.5420 (5) Å

  • c = 11.3748 (8) Å

  • V = 1051.80 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 173 K

  • 0.25 × 0.13 × 0.05 mm

Data collection
  • Bruker APEXII diffractometer

  • 6908 measured reflections

  • 1365 independent reflections

  • 1003 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.121

  • S = 1.05

  • 1365 reflections

  • 109 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N10-H10...Cl1 0.93 2.44 2.912 (2) 111
N10-H10...O8 0.93 2.00 2.616 (3) 122

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2108 ).


Acknowledgements

The authors would like to thank the Deanship of Scientific Research at the Islamic University of Gaza for their financial support to RYM, BAAT and AMA. Thanks are due to the graduate students Rasha Alsalahat and Huda Hammouda for their practical scientific contribution.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Awadallah, A. M., Seppelt, K. & Shorafa, H. (2006). Tetrahedron, 62, 7744-7746.  [ISI] [CSD] [CrossRef] [ChemPort]
Awadallah, A. & Zahra, J. (2008). Molecules, 13, 170-176.  [CrossRef] [PubMed] [ChemPort]
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Budarina, E. V., Dolgushina, T. S., Petrov, M. L., Labeish, N. N., Koltsov, A. A. & Belskii, K. (2007). Russ. J. Org. Chem. 43, 1516-1525.  [ISI] [CrossRef] [ChemPort]
Shawalia, A. S. & Samy, N. A. (2009). The Open Bioactive Compd J. 2, 8-16.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Thaher, B. A., Zahra, J. A. & El-Abadelah, M. M. (2002). J. Heterocycl. Chem. 39, 901-904.  [ChemPort]


Acta Cryst (2013). E69, o72  [ doi:10.1107/S1600536812049938 ]

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