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Volume 68 
Part 12 
Page o3483  
December 2012  

Received 17 November 2012
Accepted 23 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.090
Data-to-parameter ratio = 18.3
Details
Open access

1-(2-Chlorobenzoyl)-3-(2,3-dimethylphenyl)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: mkhawarrauf@yahoo.co.uk, aminbadshah@yahoo.com

The dihedral angle between the two phenyl groups in the title compound, C16H15ClN2OS, is 14.88 (4)°. An intramolecular N-H...O hydrogen bond occurs. In the crystal, pairs of N-H...S hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For background 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
  • C16H15ClN2OS

  • Mr = 318.81

  • Triclinic, [P \overline 1]

  • a = 7.489 (3) Å

  • b = 9.338 (4) Å

  • c = 13.274 (5) Å

  • [alpha] = 65.674 (13)°

  • [beta] = 69.975 (16)°

  • [gamma] = 73.639 (17)°

  • V = 783.9 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 123 K

  • 0.50 × 0.35 × 0.28 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • 6180 measured reflections

  • 3506 independent reflections

  • 3373 reflections with I > 2[sigma](I)

  • Rint = 0.062

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

  • wR(F2) = 0.090

  • S = 1.08

  • 3506 reflections

  • 192 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.31 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 2.46 3.3104 (15) 164
N2-H2...O1 0.88 2.00 2.6866 (17) 134
Symmetry code: (i) -x, -y, -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. Cryst. Soc. Jpn, 51, 218-224.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5274 ).


Acknowledgements

MR 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. Cryst. 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 (2012). E68, o3483  [ doi:10.1107/S1600536812048209 ]

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