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

Thiam, E.I.; Diop, M.; Gaye, M.; Sall, A.S.; Barry, A.H.

doi:10.1107/S1600536808008374

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 (C-C) = 0.003 Å
R = 0.047
wR = 0.118
Data-to-parameter ratio = 17.2
Details

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

Elhadj Ibrahima Thiam,^a Mayoro Diop,^a Mohamed Gaye,^a Abdou Salam Sall ^a and Aliou Hamady Barry ^b ^*

^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-HO and N-HS hydrogen bonds.

Related literature

For related structures: see Arslan et al. (2004); Avsar et al. (2003).

Experimental

Crystal data

C₂₂H₁₈N₄O₂S₂
M_r = 434.52
Triclinic, $[P \overline 1]$
a = 7.179 (1) Å
b = 12.064 (2) Å
c = 12.476 (2) Å
= 77.88 (5)°
= 86.96 (5)°
= 77.91 (5)°
V = 1032.9 (3) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.118
S = 1.04
4671 reflections
271 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-HN1O6	0.88	1.88	2.633 (2)	142
N2-HN2O7	0.88	1.99	2.680 (2)	134
N4-HN4S2ⁱ	0.88	2.61	3.478 (2)	170
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Nonius, 1998); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); 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.
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.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds