1-Benzoyl-3-(4-chloro­phen­yl)thio­urea dichloro­methane hemisolvate

Selvakumaran, N.; Sheeba, M.M.; Karvembu, R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812045588

Volume 68
Part 12
Page o3313
December 2012

Received 4 November 2012
Accepted 5 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.090
Data-to-parameter ratio = 15.1
Details

1-Benzoyl-3-(4-chlorophenyl)thiourea dichloromethane hemisolvate

N. Selvakumaran,^a M. Mary Sheeba,^a R. Karvembu,^a ⁺ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India,^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title hemisolvate, C₁₄H₁₁ClN₂OS·0.5CH₂Cl₂, an anti disposition is found for the thione and ketone atoms, as well as the N-H H atoms; the dichloromethane C atom lies on a twofold axis. The central chromophore (including the two adjacent ipso C atoms) is planar (r.m.s. deviation = 0.021 Å) owing to the presence of an intramolecular N-HO hydrogen bond, which closes an S(6) loop. Significant twists are evident in the molecule, the dihedral angles between the central moiety and the phenyl and benzene rings being 29.52 (7) and 40.02 (7)°, respectively. In the crystal, eight-membered {HNC= S}₂ synthons with twofold symmetry form via N-HS hydrogen bonds. The dimers are connected into a supramolecular chain along [111] by C-HO interactions. The chains stack along the c axis, forming columns which define channels in which the occluded dichloromethane molecules reside.

Related literature

For complexation of N-benzoyl-N'-arylthiourea derivatives to transition metals, see: Selvakumaran et al. (2011). For related structures, see: Khawar Rauf et al. (2006); Selvakumaran et al. (2012).

Experimental

Crystal data

C₁₄H₁₁ClN₂OS·0.5CH₂Cl₂
M_r = 333.23
Monoclinic, C 2/c
a = 20.0800 (4) Å
b = 16.0136 (2) Å
c = 10.3752 (2) Å
= 117.690 (3)°
V = 2954.10 (9) Å³
Z = 8
Cu K radiation
= 5.26 mm^-1
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.619, T_max = 1.000
5766 measured reflections
2937 independent reflections
2802 reflections with I > 2(I)
R_int = 0.013

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.090
S = 1.05
2937 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.63 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2nO1	0.90 (2)	1.85 (2)	2.6034 (17)	140.6 (18)
N1-H1nS1ⁱ	0.87 (2)	2.59 (2)	3.4368 (15)	167 (2)
C12-H12O1ⁱⁱ	0.95	2.47	3.3743 (19)	160
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), 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: HG5268 ).

Acknowledgements

NS thanks NITT for a Fellowship. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.
Khawar Rauf, M., Badshah, A., Flörke, U. & Saeed, A. (2006). Acta Cryst. E62, o1419-o1420.
Selvakumaran, N., Ng, S. W., Tiekink, E. R. T. & Karvembu, R. (2011). Inorg. Chim. Acta, 376, 278-284.
Selvakumaran, N., Sheeba, M. M., Karvembu, R., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o3259.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds