1,1-Dibenzyl-3-(4-fluoro­benzo­yl)thio­urea

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

doi:10.1107/S1600536811026687

. 2011 Jul 9;67(Pt 8):o1987. doi: 10.1107/S1600536811026687

1,1-Dibenzyl-3-(4-fluorobenzoyl)thiourea

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: PMC3213443 PMID: 22091022

Abstract

In the title compound, C₂₂H₁₉FN₂OS, the 2-fluorobenzoyl group adopts a trans conformation with respect to the thiono S atom across the N—C bond. In the crystal, intermolecular N—H⋯S, C—H⋯S and C—H⋯O hydrogen bonds link the molecules, forming a two-dimensional network parallel to (101).

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For related structures, see: Nasir et al. (2011 ▶); Yamin & Hassan (2004 ▶); Hassan et al. (2008a ▶,b ▶,c ▶, 2009 ▶). For the synthesis, see: Hassan et al. (2008a ▶).

Experimental

Crystal data

C₂₂H₁₉FN₂OS
M _r = 378.45
Monoclinic,
a = 10.683 (3) Å
b = 7.026 (2) Å
c = 26.435 (7) Å
β = 101.100 (6)°
V = 1946.9 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 298 K
0.42 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T _min = 0.925, T _max = 0.967
8644 measured reflections
3425 independent reflections
2659 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.138
S = 1.15
3425 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 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: ORTEPIII (Burnett & Johnson, 1996 ▶), XP in SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026687/dn2702sup1.cif

e-67-o1987-sup1.cif^{(25.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026687/dn2702Isup2.hkl

e-67-o1987-Isup2.hkl^{(168KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811026687/dn2702Isup3.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	2.61	3.422 (2)	159
C1—H1A⋯S1ⁱ	0.93	2.87	3.727 (3)	154
C4—H4⋯O1ⁱⁱ	0.93	2.50	3.322 (4)	147

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

Acknowledgments

The authors thank Universiti Kebangsaan Malaysia for providing facilities and grants (postdoctoral for INH, UKM-GUP-BTT-07–30-190 and UKM-OUP-TK-16– 73/2010&2011 for MBK sabbatical leave). They also expresstheir appreciation to the Kementerian Pengajian Tinggi, Malaysia, for the research fund No. UKM-ST-06-FRGS0111–2009.

supplementary crystallographic information

Comment

The title compound, I, is a thiourea derivative of dibenzylamine analogous to our previous reported, 1,1-sibenzyl-3-(3-chlorobenzoyl)thiourea, II (Nasir et al. 2011). The molecule maintains the the same trans and cis conformation for both the 3-fluorobenzoyl and the dibenzylamine groups, respectively, relative to the S atom across the N2—C8 bond (Fig 1). The dihedral angle between the phenyl ring, (C1—C6), and the thiourea fragment, (S1/N1/N2/C8) is 70.95 (13)° , whereas in II was 72.9 (2)°. The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987) and comparable with those of II. However, the C=S bond length [1.678 (2)Å] is slightly longer than that of (II) [1.672 (6)Å]

Both phenyl rings, [C10/C11/C12/C13/C14/C15] and [C17/C18/C19/C20/C21/C22] are essentially planar and are twisted to each other by a dihedral angle of 22.4 (4)°. The intermolecular N1—H1···S1, C1—H1A···S and C4—H4···O1 hydrogen bonds (Table 1,) links the molecules into two dimensional ribbon parallel to the (1 0 1) plane (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 ethanolic solution at room temperature (yield 87%).