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Volume 69 
Part 1 
Page o84  
January 2013  

Received 29 November 2012
Accepted 7 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.082
Data-to-parameter ratio = 16.0
Details
Open access

1-(2-Chlorobenzoyl)-3-(pyrimidin-2-yl)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

In the title compound, C12H9ClN4OS, the carbonyl group is at a cis position with respect to the thiourea unit. The dihedral angle between the phenyl and pyrimidine ring is 16.49 (6)°. An intramolecular N-H...N hydrogen bond stabilizes the molecular conformation. In the crystal, N-H...N, C-H...O and C-H...S hydrogen bonds generate chains along the bc axis.

Related literature

For background to our work on structural and coordination chemistry of N,N'-disubstituted thioureas, see: Rauf et al. (2012[Rauf, M. K., Ebihara, M., Badshah, A. & Imtiaz-ud-Din, (2012). Acta Cryst. E68, o119.]). For a related structure, see: Sultana et al. (2007[Sultana, S., Khawar Rauf, M., Ebihara, M. & Badshah, A. (2007). Acta Cryst. E63, o2674.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9ClN4OS

  • Mr = 292.74

  • Triclinic, [P \overline 1]

  • a = 7.167 (3) Å

  • b = 8.000 (4) Å

  • c = 11.252 (5) Å

  • [alpha] = 81.625 (14)°

  • [beta] = 74.580 (12)°

  • [gamma] = 83.979 (15)°

  • V = 613.8 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 123 K

  • 0.30 × 0.26 × 0.18 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • 4888 measured reflections

  • 2759 independent reflections

  • 2590 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.082

  • S = 1.07

  • 2759 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N3 0.88 1.93 2.611 (2) 133
N2-H2...N4i 0.88 2.21 3.068 (2) 166
C11-H11...O1ii 0.95 2.28 3.200 (2) 163
C12-H12...S1i 0.95 2.77 3.568 (2) 142
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) x-1, y+1, z.

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 (Molecular Structure Corporation & Rigaku, 2001[Molecular Structure Corporation & Rigaku (2001). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); 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 2009 (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: PV2612 ).


Acknowledgements

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

References

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]
Sultana, S., Khawar Rauf, M., Ebihara, M. & Badshah, A. (2007). Acta Cryst. E63, o2674.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o84  [ doi:10.1107/S1600536812050118 ]

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