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Volume 64 
Part 5 
Page o776  
May 2008  

Received 18 February 2008
Accepted 27 March 2008
Online 2 April 2008

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.118
Data-to-parameter ratio = 17.2
Details
Open access

1,2-Bis(N'-benzoylthioureido)benzene

aDépartement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and bDépartement de Chimie, Faculté des Sciences, Université de Nouakchott, Nouakchott, Mauritania
Correspondence e-mail: mlgayeastou@yahoo.fr

The title compound, C22H18N4O2S2, was characterized by 1H and 13C NMR, solid-state IR spectroscopy and X-ray crystallographic techniques. The crystal structure determination reveals that the twisting modes of the two side arms are different [C-N-C-O and C-N-C-N torsion angles = -1.2 (3) and 1.1 (3)°, respectively, in one arm and 24.1 (3) and -5.1 (3)°, respectively, in the other]. The crystal structure involves N-H...O and N-H...S hydrogen bonds.

Related literature

For related structures: see Arslan et al. (2004[Arslan, H., Flörke, U. & Külcü, N. (2004). Acta Chim. Slov. 51, 787-792.]); Avsar et al. (2003[Avsar, G., Arslan, H., Haupt, H.-J. & Külcü, N. (2003). Turk. J. Chem. 27, 281-285.]).

[Scheme 1]

Experimental

Crystal data
  • C22H18N4O2S2

  • Mr = 434.52

  • Triclinic, [P \overline 1]

  • a = 7.179 (1) Å

  • b = 12.064 (2) Å

  • c = 12.476 (2) Å

  • [alpha] = 77.88 (5)°

  • [beta] = 86.96 (5)°

  • [gamma] = 77.91 (5)°

  • V = 1032.9 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 173 (2) K

  • 0.10 × 0.10 × 0.10 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: none

  • 12922 measured reflections

  • 4671 independent reflections

  • 3234 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.118

  • S = 1.04

  • 4671 reflections

  • 271 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-HN1...O6 0.88 1.88 2.633 (2) 142
N2-HN2...O7 0.88 1.99 2.680 (2) 134
N4-HN4...S2i 0.88 2.61 3.478 (2) 170
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT and DENZO. Nonius BV, Delft, The Netherland.]); cell refinement: DENZO (Nonius, 1998[Nonius (1998). COLLECT and DENZO. Nonius BV, Delft, The Netherland.]); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WW2115 ).


Acknowledgements

The authors thank the Fondation SONATEL for financial support (CDP 75/06) and Professor R. Welter (Laboratoire DECOMET, UMR CNRS, Université Louis Pasteur 4, Strasbourg, France) for assistance.

References

Arslan, H., Flörke, U. & Külcü, N. (2004). Acta Chim. Slov. 51, 787-792.  [ChemPort]
Avsar, G., Arslan, H., Haupt, H.-J. & Külcü, N. (2003). Turk. J. Chem. 27, 281-285.
Nonius (1998). COLLECT and DENZO. Nonius BV, Delft, The Netherland.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [CrossRef] [details]


Acta Cryst (2008). E64, o776  [ doi:10.1107/S1600536808008374 ]

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