2-Bromo-N-(dibenzyl­carbamothioyl)benzamide

Mohd Faizal Md Nasir; Ibrahim N Hassan; Wan Ramli Wan Daud; Bohari M Yamin; Mohammad B Kassim

doi:10.1107/S1600536811014711

. 2011 Apr 29;67(Pt 5):o1218. doi: 10.1107/S1600536811014711

2-Bromo-N-(dibenzylcarbamothioyl)benzamide

Mohd Faizal Md Nasir ^a, Ibrahim N Hassan ^a,^*, Wan Ramli Wan Daud ^b,^a, Bohari M Yamin ^c, Mohammad B Kassim ^c,^a

PMCID: PMC3089282 PMID: 21754516

Abstract

The 2-bromobenzoyl group in the title compound, C₂₂H₁₉BrN₂OS, adopts an E conformation with respect to the thiono S atom across the N—C bond. In the crystal structure, the molecule is stablized by N—H⋯O intermolecular hydrogen bonds, forming a one-dimensional chain along the b axis.

Related literature

For related structures, see: Yamin & Hassan (2004 ▶); Hassan et al. (2008a ▶,b ▶,c ▶, 2009 ▶). For the synthesis, see: Hassan et al. (2008a ▶). For reference bond distances, see: Allen et al. (2004 ▶).

Experimental

Crystal data

C₂₂H₁₉BrN₂OS
M _r = 439.36
Tetragonal,
a = 12.2833 (16) Å
c = 14.002 (4) Å
V = 2112.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.06 mm⁻¹
T = 273 K
0.35 × 0.31 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.533, T _max = 0.649
15683 measured reflections
5217 independent reflections
2506 reflections with I > 2σ(I)
R _int = 0.064

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.118
S = 0.93
5217 reflections
244 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), with 2474 Friedel pairs
Flack parameter: −0.001 (11)

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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), PARST (Nardelli, 1995 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014711/dn2677sup1.cif

e-67-o1218-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014711/dn2677Isup2.hkl

e-67-o1218-Isup2.hkl^{(255.5KB, 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—H1A⋯Br1	0.86	2.79	3.220 (3)	113
N1—H1A⋯O1ⁱ	0.86	2.20	2.903 (4)	139

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Universiti Kebangsaan Malaysia for providing facilities and grants (postdoctoral for INH, grant Nos. UKM-GUP-BTT-07-30-190 and UKM-OUP-TK-16-73/2010), and the Kementerian Pengajian Tinggi, Malaysia, for research fund No. UKM-AP-TK-05-2009.

supplementary crystallographic information

Comment

The title compound, I, is a thiourea derivative of dibenzylamine analogous to our previous reported, ethyl-2-(3-benzoylthioureido)acetate (Hassan et al., 2008a), propyl-2-(3-benzoylthioureido)acetate (Hassan et al., 2008b), butyl-2-(3-benzoylthioureido)acetate (Hassan et al., 2008c) and 1-(2-morpholinoethyl)-3-(3-phenylacryloyl)thiourea (Yamin & Hassan, 2004). The molecule has the 2-bromobenzoyl group adopting an E conformation, with respect to the thiono S atom across the N1—C8 bond, whereas both the phenyl ring of the dibenzylamine group adopt E and Z conformation relative to the S atom across the N2—C8 bond (Fig. 1). The phenyl ring, (C1–C6), and the thiourea fragment, (S1/N1/N2/C8), are essentially planar and the dihedral angle between them is 72.9 (2)°. The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987).

Both phenyl rings, [C10/C11/C12/C13/C14/C15] and [C17/C18/C19/C20/C21/C22] are essentially planar and they are twisted to each other by a dihedral angle of 22.4 (4)°. There is weak intramolecular hydrogen bond, N1—H1A···Br1 (Table 1). As a result, one pseudo-six-membered ring (N1/H1A/Br1/C1/C6/C7) is formed. The intermolecular N1—H1A···O1 hydrogen bonds (Table 1,) links the molecules into a chain parallel to the b axis (Fig. 2).

Experimental

The title compound was synthesized according to a previously reported compound (Hassan et al., 2008a). A colourless crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from methanolic solution at room temperature (yield 83%).