N-Benzyl­carbamothioyl-2-chloro­benzamide

Xi Zheng; Bo Li; Qiang Wang; Li Guo

doi:10.1107/S1600536810023822

. 2010 Jun 26;66(Pt 7):o1774. doi: 10.1107/S1600536810023822

N-Benzylcarbamothioyl-2-chlorobenzamide

Xi Zheng ^a, Bo Li ^a, Qiang Wang ^a, Li Guo ^a,^*

PMCID: PMC3006700 PMID: 21587987

Abstract

In the title compound, C₁₅H₁₃ClN₂OS, the dihedral angles between the sulfourea group and the benzene ring and the chlorobenzene ring are 35.8 (6) and 81.6 (6)° respectively. An intramolecular N—H⋯O interaction occurs. In the crystal, a combination of intermolecular π–π stacking interactions [centroid–centroid distance = 4.0616 (16) Å] and N—H⋯S hydrogen bonds stabilizes the structure.

Related literature

For general background to the chemistry and biological activity of thiourea derivatives and their use, see: Jain & Rao (2003 ▶); Zeng et al. (2003 ▶); Xu et al. (2004 ▶); Zheng et al. (2004 ▶); D’hooghe et al. (2005 ▶); Saeed et al. (2008 ▶, 2009 ▶, 2010 ▶).

Experimental

Crystal data

C₁₅H₁₃ClN₂OS
M _r = 304.78
Triclinic,
a = 7.347 (2) Å
b = 9.658 (3) Å
c = 11.003 (3) Å
α = 110.150 (5)°
β = 90.767 (3)°
γ = 104.058 (3)°
V = 707.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 153 K
0.40 × 0.30 × 0.30 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.852, T _max = 0.886
5691 measured reflections
2481 independent reflections
2194 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.073
S = 1.01
2481 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023822/pk2248sup1.cif

e-66-o1774-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023822/pk2248Isup2.hkl

e-66-o1774-Isup2.hkl^{(121.9KB, hkl)}

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—H1N⋯S1ⁱ	0.86 (2)	2.53 (2)	3.3698 (18)	166.2 (18)
N2—H2N⋯O1	0.82 (2)	2.01 (2)	2.669 (2)	137 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

supplementary crystallographic information

Comment

N-(benzylcarbamothioyl)-2-chlorobenzamide derivatives are of great importance owing to their wide-ranging biological properties (Zeng et al. (2003)). The title compound is one of the key intermediates in our synthetic investigations of antiviral drugs. We report here its crystal structure. As shown in Fig. 1, the dihedral angle of 35.8 (6)° and 81.6 (6)° between the connecting sulfourea unit and the benzene ring, and between the 2-chloro-benzene ring and the connecting sulfourea group, respectively. A combination of intermolecular π-π packing interaction, N—H···O and N—H···S hydrogen bonds help stabilize the structure. In addition, weak C—H···π interactions are also present.

Experimental

A solution of 0.23 g (3 mmol) of ammonium thiocyanate in 7 ml of acetonitrile was added to a solution of 0.52 g (3 mmol) of 2-chlorobenzoyl chloride in 2.5 ml of toluene. The mixture was heated for 5 min at 40°C and filtered from ammonium chloride, the filtrate was added to a solution of 0.32 g (3 mmol) of phenylmethanamine in 5 ml of acetonitrile, the mixture was stirred for 3 h at room temperature and evaporated, and the residue was washed with ethanol and recrystallized from ethanol. Yield 0.77 g (85%). Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of dichloromethane.