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Volume 70 
Part 1 
Page o34  
January 2014  

Received 4 November 2013
Accepted 2 December 2013
Online 11 December 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.097
Data-to-parameter ratio = 14.3
Details
Open access

N-(2-Chloro-5-nitro­phen­yl)-N'-(3-chloro­propion­yl)thio­urea

aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
Correspondence e-mail: ctfairus@ukm.my

The title compound, C10H9Cl2N3O3S, adopts a trans-cis conformation with respect to the position of chloropropionyl and chloronitrobenzene groups respectively, against the thiono about their C-N bonds. The conformation is stabilized by an intra­molecular N-H...O hydrogen bond. In the crystal, there is a short Cl...Cl contact with a distance of 3.386 (13) Å.

Related literature

For related structures, see: Othman et al. (2010[Othman, E. A., Soh, S. K. C. & Yamin, B. M. (2010). Acta Cryst. E66, o628.]); Yamin et al. (2011[Yamin, B. M., Othman, N. E. A., Yusof, M. S. M. & Embong, F. (2011). Acta Cryst. E67, o419.]); Yamin & Othman (2011[Yamin, B. M. & Othman, N. E. A. (2011). Acta Cryst. E67, o1629.]); Yusof et al., (2011[Yusof, M. S. M., Embong, N. F., Othman, E. A. & Yamin, B. M. (2011). Acta Cryst. E67, o1849.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9Cl2N3O3S

  • Mr = 322.16

  • Monoclinic, C 2/c

  • a = 21.764 (6) Å

  • b = 5.2284 (13) Å

  • c = 24.134 (6) Å

  • [beta] = 106.388 (8)°

  • V = 2634.6 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.66 mm-1

  • T = 298 K

  • 0.38 × 0.36 × 0.27 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.902, Tmax = 0.919

  • 12266 measured reflections

  • 2460 independent reflections

  • 2116 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.097

  • S = 1.05

  • 2460 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1 0.86 1.87 2.596 (2) 142

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: FJ2651 ).


Acknowledgements

The authors would like to thank the Universiti Kebangsaan Malaysia for research grants DLP-2013-009 and DIP-2012-11 and the Centre of Research and Instrumentation (CRIM) for research facilities.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Othman, E. A., Soh, S. K. C. & Yamin, B. M. (2010). Acta Cryst. E66, o628.  [CSD] [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]
Yamin, B. M. & Othman, N. E. A. (2011). Acta Cryst. E67, o1629.  [CSD] [CrossRef] [IUCr Journals]
Yamin, B. M., Othman, N. E. A., Yusof, M. S. M. & Embong, F. (2011). Acta Cryst. E67, o419.  [CSD] [CrossRef] [IUCr Journals]
Yusof, M. S. M., Embong, N. F., Othman, E. A. & Yamin, B. M. (2011). Acta Cryst. E67, o1849.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2014). E70, o34  [ doi:10.1107/S1600536813032662 ]

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