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Volume 69 
Part 11 
Page o1696  
November 2013  

Received 20 September 2013
Accepted 17 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.053
wR = 0.116
Data-to-parameter ratio = 15.4
Details
Open access

1-(4-Chlorophenyl)-3-(3-chloro­pro­pionyl)thio­urea

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

In the title compound, C10H10Cl2N2OS, the mol­ecule adopts a trans-cis conformation with respect to the position of the carbonyl group and the chloro­phenyl groups relative to the thiono group across the C-N bonds. The mol­ecule is stabilized by an N-H...O hydrogen bond. In the crystal, mol­ecules are linked by N-H...S and C-H...O hydrogen bonds, forming zigzag chains along the b-axis direction. C-H...[pi] inter­actions are also present.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related thio­urea derivatives, 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
  • C10H10Cl2N2OS

  • Mr = 277.16

  • Triclinic, [P \overline 1]

  • a = 5.5151 (16) Å

  • b = 9.045 (3) Å

  • c = 12.387 (4) Å

  • [alpha] = 101.000 (5)°

  • [beta] = 94.027 (5)°

  • [gamma] = 94.780 (5)°

  • V = 602.1 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.69 mm-1

  • T = 298 K

  • 0.47 × 0.21 × 0.08 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 = 0.737, Tmax = 0.947

  • 5947 measured reflections

  • 2227 independent reflections

  • 1698 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.116

  • S = 1.22

  • 2227 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5-C10 benzene ring.

D-H...A D-H H...A D...A D-H...A
N2-H2A...O1 0.86 1.92 2.646 (4) 141
N1-H1A...S1i 0.86 2.52 3.367 (3) 169
C9-H9A...O1ii 0.93 2.55 3.402 (5) 152
C1-H1B...Cg1iii 0.97 2.92 3.690 (4) 137
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x-1, -y, -z+1; (iii) -x, -y, -z+1.

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, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) 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: LR2115 ).


Acknowledgements

The authors would like to thank Universiti Kebangsaan Malaysia and the Ministry of Science and Technology, Malaysia for research grants GGPM-2012-015 and DIP-2012-11, and the Centre of Research and Instrumentation (CRIM) for research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
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 (2013). E69, o1696  [ doi:10.1107/S1600536813028511 ]

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