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Volume 69 
Part 10 
Page o1567  
October 2013  

Received 28 August 2013
Accepted 13 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.045
wR = 0.117
Data-to-parameter ratio = 13.2
Details
Open access

3-Chloro-N-[N-(furan-2-carbonyl)hydrazinocarbothioyl]benzamide

aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
Correspondence e-mail: Aishah80@ukm.my

In the title compound C13H10ClN3O3S, the benzoyl group maintains its trans conformation against the thiono group about the C-N bond and the intramolecular hydrogen bond between the benzoyl O atom and thioamide H atom. In the crystal, N-H...O and C-H...O hydrogen bonds link the molecules, forming chains along the b-axis direction. In addition, C-H...[pi] interactions occur between a phenyl H atom and the furan ring.

Related literature

For bond-lengths data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987).]) and for a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For related structures of thiourea derivatives, see: Yamin & Yusof (2003[Yamin, B. M. & Yusof, M. S. M. (2003). Acta Cryst. E59, o124-o126.]); Yusof et al. (2003[Yusof, M. S. M., Yamin, B. M. & Shamsuddin, M. (2003). Acta Cryst. E59, o810-o811.]); Ali et al. (2004[Ali, H., Yusof, M. S., Khamis, N. A., Mardi, A. S. & Yamin, B. M. (2004). Acta Cryst. E60, o1656-o1658.]); Venkatachalam et al. (2004[Venkatachalam, T. K., Mao, C. & Uckun, F. M. (2004). Bioorg. Med. Chem. 12, 4275-4284.]); Saeed et al. (2011[Saeed, S., Rashid, N., Jones, P. G. & Tahir, A. (2011). J. Heterocycl. Chem. 48, 74-84.]); Wilson et al. (2010[Wilson, D., Arada, M. de los, Á., Alrgret, S. & del Valle, M. (2010). J. Hazard. Mater. 181, 140-146.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10ClN3O3S

  • Mr = 323.75

  • Orthorhombic, P b c a

  • a = 7.286 (4) Å

  • b = 15.148 (8) Å

  • c = 25.840 (14) Å

  • V = 2852 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.43 mm-1

  • T = 298 K

  • 0.50 × 0.49 × 0.12 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.815, Tmax = 0.951

  • 15224 measured reflections

  • 2507 independent reflections

  • 1723 reflections with I > 2[sigma](I)

  • Rint = 0.082

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.117

  • S = 1.02

  • 2507 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the furan ring.

D-H...A D-H H...A D...A D-H...A
N2-H2A...O1 0.86 1.92 2.574 (3) 132
N1-H1A...O2i 0.86 2.25 3.094 (3) 167
C5-H5A...O2i 0.93 2.32 3.093 (4) 140
C13-H13A...Cgii 0.93 2.83 3.516 (4) 132
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]; (ii) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. 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: BG2516 ).


Acknowledgements

The authors would like to thank Universiti Kebangsaan Malaysia and the Ministry of Science and Technology, Malaysia, for research grants FRGS/1/213/ST01/UKM/03/4 and DIP-2012-11 and the Centre of Research and Instrumentation (CRIM) for the research facilities.

References

Ali, H., Yusof, M. S., Khamis, N. A., Mardi, A. S. & Yamin, B. M. (2004). Acta Cryst. E60, o1656-o1658.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987).
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Saeed, S., Rashid, N., Jones, P. G. & Tahir, A. (2011). J. Heterocycl. Chem. 48, 74-84.  [CSD] [CrossRef] [ChemPort]
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]
Venkatachalam, T. K., Mao, C. & Uckun, F. M. (2004). Bioorg. Med. Chem. 12, 4275-4284.  [CrossRef] [PubMed] [ChemPort]
Wilson, D., Arada, M. de los, Á., Alrgret, S. & del Valle, M. (2010). J. Hazard. Mater. 181, 140-146.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Yamin, B. M. & Yusof, M. S. M. (2003). Acta Cryst. E59, o124-o126.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Yusof, M. S. M., Yamin, B. M. & Shamsuddin, M. (2003). Acta Cryst. E59, o810-o811.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1567  [ doi:10.1107/S1600536813025440 ]

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