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Volume 69 
Part 1 
Page o16  
January 2013  

Received 27 November 2012
Accepted 28 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.031
wR = 0.075
Data-to-parameter ratio = 14.4
Details
Open access

1-(2-Chlorobenzoyl)-3-(2-trifluoromethylphenyl)thiourea

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and bDepartment of Chemistry, Faculty of Engineering, Gifu University Yanagido, Gifu 501-1193, Japan
Correspondence e-mail: aminbadshah@yahoo.com, mkhawarrauf@yahoo.co.uk

The dihedral angle between the benzene rings in the title compound, C15H10ClF3N2OS, is 54.02 (4)°. An intramolecular N-H...O hydrogen bond occurs. In the crystal, N-H...S hydrogen bonds link the molecules into inversion dimers.

Related literature

For our previous work on the structural and coordination chemistry of N,N'-disubstituted thioureas and a related structure, see: Rauf et al. (2012[Rauf, M. K., Ebihara, M., Badshah, A. & Imtiaz-ud-Din (2012). Acta Cryst. E68, o119.]). For a description of the Cambridge Structural Database, see: Allen et al. (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10ClF3N2OS

  • Mr = 358.76

  • Triclinic, [P \overline 1]

  • a = 7.705 (3) Å

  • b = 8.348 (3) Å

  • c = 12.465 (5) Å

  • [alpha] = 84.92 (1)°

  • [beta] = 72.913 (9)°

  • [gamma] = 86.272 (11)°

  • V = 762.7 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.42 mm-1

  • T = 123 K

  • 0.45 × 0.36 × 0.28 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • 5989 measured reflections

  • 3408 independent reflections

  • 3240 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.075

  • S = 1.07

  • 3408 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...S1i 0.88 2.58 3.4032 (16) 157
N2-H2...O1 0.88 1.91 2.6179 (16) 136
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001[Molecular Structure Corporation & Rigaku (2001). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: Yadokari-XG (Wakita, 2001[Wakita, K. (2001). Yadokari-XG. http://www.hat.hi-ho.ne.jp/k-wakita/yadokari .]; Kabuto et al., 2009[Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Crystallogr. Soc. Jpn, 51, 218-224.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5276 ).


Acknowledgements

MKR is grateful to The Quaid-i-Azam University, Islamabad, for financial support for a postdoctoral fellowship.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
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]
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Crystallogr. Soc. Jpn, 51, 218-224.  [CrossRef]
Molecular Structure Corporation & Rigaku (2001). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Rauf, M. K., Ebihara, M., Badshah, A. & Imtiaz-ud-Din (2012). Acta Cryst. E68, o119.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wakita, K. (2001). Yadokari-XG. http://www.hat.hi-ho.ne.jp/k-wakita/yadokari .


Acta Cryst (2013). E69, o16  [ doi:10.1107/S1600536812048829 ]

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