1,1-Dibenzyl-3-(3-chloro­benzo­yl)thio­urea

Mohd Faizal Md Nasir; Ibrahim N Hassan; Bohari Yamin; W R W Daud; Mohammad B Kassim

doi:10.1107/S1600536811023191

. 2011 Jun 18;67(Pt 7):o1742. doi: 10.1107/S1600536811023191

1,1-Dibenzyl-3-(3-chlorobenzoyl)thiourea

Mohd Faizal Md Nasir ^a, Ibrahim N Hassan ^a, Bohari Yamin ^b, W R W Daud ^c,^a, Mohammad B Kassim ^b,^a,^*

PMCID: PMC3151829 PMID: 21837130

Abstract

In the title compound, C₂₂H₁₉ClN₂OS, the thiono and carbonyl groups are trans positioned with respect to a partially double C—N bond. The amide group is twisted relative to the thiourea fragment, forming a dihedral angle of 46.75 (11)°. In the crystal, intermolecular N—H⋯S and C—H⋯O hydrogen bonds link the molecules into a one-dimensional polymeric structure parallel to the c axis.

Related literature

For related structures and background references, see: Al-abbasi & Kassim (2011 ▶); Nasir et al. (2011 ▶). For metal complexes of benzoylthioureas, see: Weiqun et al. (2005 ▶); Circu et al. (2009 ▶). For the synthetic procedure, see: Hassan et al. (2008 ▶).

Experimental

Crystal data

C₂₂H₁₉ClN₂OS
M _r = 394.90
Triclinic,
a = 9.503 (4) Å
b = 9.650 (4) Å
c = 12.487 (5) Å
α = 72.422 (8)°
β = 72.869 (9)°
γ = 69.463 (8)°
V = 999.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.28 × 0.17 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.918, T _max = 0.961
13666 measured reflections
5000 independent reflections
2879 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.147
S = 1.03
5000 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023191/gk2383sup1.cif

e-67-o1742-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023191/gk2383Isup2.hkl

e-67-o1742-Isup2.hkl^{(244.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023191/gk2383Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.86	2.74	3.410 (2)	136
C15—H15⋯O1ⁱⁱ	0.93	2.50	3.421 (3)	170

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank Universiti Kebangsaan Malaysia for grants UKM-GUP-BTT-07–30-190 and UKM-OUP-TK-16–73/2010 and sabbatical leave for MBK. They also thank the Kementerian Pengajian Tinggi, Malaysia, for the research fund No. UKM-ST-06-FRGS0111–2009.

supplementary crystallographic information

Comment

Benzoylthiourea compounds contain strong donor groups (carbonyl and thioamide) which make them very attractive ligands in coordination chemistry. These ligands react with transition metals, mostly in monoanionic and bidentate form by deprotonation of the amide group, forming neutral complexes with S, O-coordination (Weiqun et al., 2005; Circu et al., 2009).

The title compound, I, is a thiourea derivative analogous to our previously reported compounds (Nasir et al., 2011; Al-abbasi & Kassim, 2011). The thiono S and the carbonyl O atoms are trans positioned at a partially double N1-C8 bond with C7N1C8S1 torsion angle of 127.37 (18)°. The dihedral angle between the mean planes of the thiourea (S1/N1/N2/C8) and the amide group (O1/N1/C1/C7) is 46.75 (11)°. The mean planes of the dibenzylamine (C9/C10/C11/C12/C13/C14/C15 and C16/C17/C18/C19/C19/C20/C21) make an angle of 20.54 (13)°.

Intermolecular N—H···S and C—H···O hydrogen bonds link the molecules into a one dimensional polymeric structure parallel to the c-axis.

Experimental

The title compound was prepared according to a previously reported compound (Hassan et al., 2008). A colourless crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from a mixture of acetone/ethanol solution at room temperature (yield 80%).