3-Benzoyl-1,1-dibenzyl­thio­urea

Gunasekaran, N.; Karvembu, R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536810036226

Volume 66
Part 10
Pages o2572-o2573
October 2010

Received 16 August 2010
Accepted 8 September 2010
Online 18 September 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R = 0.058
wR = 0.157
Data-to-parameter ratio = 18.0
Details

3-Benzoyl-1,1-dibenzylthiourea

N. Gunasekaran,^a R. Karvembu,^a ⁺ Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

Two independent thiourea molecules comprise the asymmetric unit of the title compound, C₂₂H₂₀N₂OS. The central N-C(=S)N(H)C(=O) atoms in each molecule are virtually superimposable and each is twisted [C-N-C-S torsion angles = 121.3 (3) and -62.3 (4)°]. The molecules differ only in terms of the relative orientations of the benzyl benzene rings [major difference between the C-N-C-C torsion angles of -146.6 (3) and -132.9 (3)°]. The presence of N-HS hydrogen bonding leads to the formation of supramolecular chains along the a axis. These are consolidated in the crystal packing by C-HO interactions. The crystal was found to be a combined non-merohedral and racemic twin (twin law $[\overline{1}]$ 00/0 $[\overline{1}]$ 0/001), with the fractional contribution of the minor components being approximately 9 and 28%.

Related literature

For our studies of thiourea and its derivatives, see: Gunasekaran et al. (2010). For the biological activity of thiourea derivatives, see: Venkatachalam et al. (2004); Yuan et al. (2001); Zhou et al. (2004). For additional geometric analysis, see: Spek (2009).

Experimental

Crystal data

C₂₂H₂₀N₂OS
M_r = 360.46
Monoclinic, P 2₁
a = 7.7338 (5) Å
b = 24.3478 (16) Å
c = 9.8593 (6) Å
= 90.074 (1)°
V = 1856.5 (2) Å³
Z = 4
Mo K radiation
= 0.19 mm^-1
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.946, T_max = 0.982
17536 measured reflections
8469 independent reflections
7807 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.157
S = 1.03
8469 reflections
470 parameters
1 restraint
H-atom parameters constrained
_max = 1.27 e Å^-3
_min = -0.36 e Å^-3
Absolute structure: Flack (1983), 4101 Friedel pairs
Flack parameter: 0.25 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2S2	0.86	2.54	3.334 (3)	154
N4-H4S1ⁱ	0.86	2.54	3.334 (3)	154
C13-H13O2ⁱⁱ	0.95	2.57	3.193 (5)	124
C14-H14O2ⁱⁱ	0.95	2.60	3.207 (5)	122
C25-H25O1ⁱⁱⁱ	0.95	2.55	3.228 (4)	129
Symmetry codes: (i) x-1, y, z; (ii) $[-x+3, y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5120 ).

Acknowledgements

NG thanks the NITT for a Fellowship. The authors also thank the University of Malaya for support of the crystallographic facility.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.
Gunasekaran, N., Karvembu, R., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2113.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Venkatachalam, T. K., Mao, C. & Uckun, F. M. (2004). Bioorg. Med. Chem. 12, 4275-4284.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Yuan, Y. F., Wang, J. T., Gimeno, M. C., Laguna, A. & Jones, P. G. (2001). Inorg. Chim. Acta, 324, 309-317.
Zhou, W. Q., Li, B. L., Zhu, L. M., Ding, J. G., Yong, Z., Lu, L. & Yang, X. J. (2004). J. Mol. Struct. 690, 145-150.

organic compounds