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Volume 68 
Part 1 
Page o119  
January 2012  

Received 2 December 2011
Accepted 7 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.084
Data-to-parameter ratio = 17.2
Details
Open access

1-Benzoyl-3-(2,4,5-trichlorophenyl)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: khawar_rauf@hotmail.com

The benzene and phenyl rings in the title compound, C14H9Cl3N2OS, form a dihedral angle of 40.98 (6)°. The molecule exists in the thione form with typical thiourea C-S [1.666 (2) Å] and C-O [1.227 (3) Å] bond lengths as well as shortened C-N bonds [1.345 (3) and 1.386 (2) Å]. An intramolecular N-H...O hydrogen bond stabilizes the molecular conformation. In the crystal, pairs of N-H...S hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For information on thiourea derivatives, see: Patil & Chedekel (1984[Patil, D. G. & Chedekel, M. R. (1984). J. Org. Chem. 49, 997-1000.]); Baily et al. (1996[Baily, N., Dean, A. W., Judd, D. B., Middlemiss, D., Storer, R. & Watson, S. P. (1996). Bioorg. Med. Chem. Lett. 6, 1409-1413.]); Namgun et al. (2001[Namgun, L., Mi-Hyun, C. & Taek, H. K. (2001). J. Korean Chem. Soc. 45, 96-99.]); Koch (2001[Koch, K. R. (2001). Coord. Chem. Rev. 216-217, 473-488.]); Wegner et al. (1986[Wegner, P., Hans, R., Frank, H. & Joppien, H. (1986). Eur. Patent No. 190611.]); Krishnamurthy et al. (1999[Krishnamurthy, R., Govindaraghavan, S. & Narayanasamy, J. (1999). J. Pestic. Sci. 52, 145-151.]); Murtaza et al. (2009a[Murtaza, G., Ebihara, M., Said, M., Khawar Rauf, M. & Anwar, S. (2009a). Acta Cryst. E65, o2297-o2298.],b[Murtaza, G., Hanif-Ur-Rehman, Khawar Rauf, M., Ebihara, M. & Badshah, A. (2009b). Acta Cryst. E65, o343.]). For related structures, see: Khawar Rauf et al. (2009a[Khawar Rauf, M., Bolte, M. & Badshah, A. (2009a). Acta Cryst. E65, o177.],b[Khawar Rauf, M., Bolte, M. & Badshah, A. (2009b). Acta Cryst. E65, o240.]). 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 a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9Cl3N2OS

  • Mr = 359.64

  • Monoclinic, C 2/c

  • a = 33.111 (8) Å

  • b = 3.8413 (7) Å

  • c = 25.220 (6) Å

  • [beta] = 115.995 (2)°

  • V = 2883.1 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.78 mm-1

  • T = 296 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Rigaku, 1998[Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.800, Tmax = 1.000

  • 11264 measured reflections

  • 3264 independent reflections

  • 2686 reflections with I > 2[sigma](I)

  • Rint = 0.039

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

  • wR(F2) = 0.084

  • S = 1.06

  • 3264 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.86 1.89 2.586 (2) 137
N2-H2...S1i 0.86 2.83 3.6771 (19) 168
Symmetry code: (i) [-x+1, y, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Molecular Structure Corporation and Rigaku, 2001[Molecular Structure Corporation and 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.]) and TEXSAN (Molecular Structure Corporation and Rigaku, 2004[Molecular Structure Corporation and Rigaku (2004). TEXSAN. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: Yadokari-XG_2009 (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: BG2439 ).


Acknowledgements

MKR is grateful to the Quaid-i-Azam University, Islamabad, for financial support for a post-doctoral fellowship.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
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.
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]
Baily, N., Dean, A. W., Judd, D. B., Middlemiss, D., Storer, R. & Watson, S. P. (1996). Bioorg. Med. Chem. Lett. 6, 1409-1413.  [CrossRef]
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.
Khawar Rauf, M., Bolte, M. & Badshah, A. (2009a). Acta Cryst. E65, o177.  [CSD] [CrossRef] [details]
Khawar Rauf, M., Bolte, M. & Badshah, A. (2009b). Acta Cryst. E65, o240.  [CSD] [CrossRef] [details]
Koch, K. R. (2001). Coord. Chem. Rev. 216-217, 473-488.  [ISI] [CrossRef] [ChemPort]
Krishnamurthy, R., Govindaraghavan, S. & Narayanasamy, J. (1999). J. Pestic. Sci. 52, 145-151.
Molecular Structure Corporation and Rigaku (2001). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Molecular Structure Corporation and Rigaku (2004). TEXSAN. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Murtaza, G., Ebihara, M., Said, M., Khawar Rauf, M. & Anwar, S. (2009a). Acta Cryst. E65, o2297-o2298.  [CSD] [CrossRef] [details]
Murtaza, G., Hanif-Ur-Rehman, Khawar Rauf, M., Ebihara, M. & Badshah, A. (2009b). Acta Cryst. E65, o343.  [CSD] [CrossRef] [details]
Namgun, L., Mi-Hyun, C. & Taek, H. K. (2001). J. Korean Chem. Soc. 45, 96-99.
Patil, D. G. & Chedekel, M. R. (1984). J. Org. Chem. 49, 997-1000.  [CrossRef] [ChemPort]
Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wegner, P., Hans, R., Frank, H. & Joppien, H. (1986). Eur. Patent No. 190611.


Acta Cryst (2012). E68, o119  [ doi:10.1107/S1600536811052780 ]

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