2,2-Diphenyl-N-{[2-(tri­fluoro­meth­yl)phen­yl]carbamo­thio­yl}acetamide

Mohd Sukeri Mohd Yusof; Nur Rafikah Razali; Suhana Arshad; Azhar Abdul Rahman; Ibrahim Abdul Razak

doi:10.1107/S1600536813018680

. 2013 Jul 13;69(Pt 8):o1255–o1256. doi: 10.1107/S1600536813018680

2,2-Diphenyl-N-{[2-(trifluoromethyl)phenyl]carbamothioyl}acetamide

Mohd Sukeri Mohd Yusof ^a, Nur Rafikah Razali ^a, Suhana Arshad ^b,^‡, Azhar Abdul Rahman ^b, Ibrahim Abdul Razak ^b,^*,^§

PMCID: PMC3793754 PMID: 24109341

Abstract

The title molecule, C₂₂H₁₇F₃N₂OS, adopts a trans–cis conformation with respect to the positions of the carbonyl and trifluoromethylbenzene groups against the thiocarbonyl group across the C—N bonds. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond with an S(6) ring motif. The trifluoromethyl-substituted benzene ring forms dihedral angles of 66.05 (9) and 47.19 (9)° with the terminal phenyl rings and is twisted from the O=C—N—(C=S)—N carbonylthiourea plane [maximum deviation = 0.0535 (12) Å], making a dihedral angle of 63.59 (8)°. In the crystal, N—H⋯O and C—H⋯F hydrogen bonds link the molecules into a layer parallel to the bc plane. A C—H⋯π interaction is also observed.

Related literature

For the biological activity of thiourea derivatives, see: Vankatachalam et al. (2001 ▶). For related structures, see: Yusof, Arshad et al. (2012 ▶); Yusof, Embong et al. (2012 ▶); Yusof, Mutalib et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). graphic file with name e-69-o1255-scheme1.jpg

Experimental

Crystal data

C₂₂H₁₇F₃N₂OS
M _r = 414.44
Orthorhombic,
a = 20.0318 (4) Å
b = 10.2866 (2) Å
c = 9.5351 (2) Å
V = 1964.79 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.56 × 0.18 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.892, T _max = 0.987
21265 measured reflections
5618 independent reflections
4608 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.081
S = 1.02
5618 reflections
270 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ▶), 2568 Freidel pairs
Flack parameter: 0.01 (6)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018680/is5283sup1.cif

e-69-o1255-sup1.cif^{(28.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018680/is5283Isup2.hkl

e-69-o1255-Isup2.hkl^{(275.1KB, hkl)}

Click here for additional data file.^{(7.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813018680/is5283Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.96 (3)	1.93 (2)	2.6237 (19)	127 (2)
N2—H1N2⋯O1ⁱ	0.81 (2)	2.04 (2)	2.838 (2)	174 (2)
C9—H9A⋯F1ⁱⁱ	0.95	2.53	3.395 (2)	151
C7—H7A⋯Cg1ⁱⁱⁱ	1.00	2.84	3.7826 (19)	158

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the USM Short Term Grant, No. 304/PFIZIK/6312078, to conduct this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme Fellowship (ASTS).

supplementary crystallographic information

Comment

Recent studies have shown that thiourea derivatives are potential biologically active agents, such as antimicrobials and HIV inhibitors (Vankatachalam et al., 2001). The molecular structure of the title compound is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Yusof, Arshad et al., 2012; Yusof, Embong et al., 2012; Yusof, Mutalib et al., 2012). The molecule adopts a trans-cis configuration with respect to the positions of diphenylmethane and trifluoromethylbenzene (F1–F3/C16–C22) groups, respectively, to the sulfur (S1) atom across the C—N bond. The trifluoromethyl-substituted benzene ring (C16–C21) forms dihedral angles of 66.05 (9) and 47.19 (9)° with the terminal phenyl rings, C1–C6 and C8–C13, respectively. Furthermore, the trifluoromethylbenzene plane (C16–C22) is slightly twisted from the carbonyl thiourea moiety (S1/O1/N1/N2/C15/C14) with a C15—N1—C16—C21 torsion angle of 119.3 (2)°. In the molecule, an intramolecular N2—H1N2···O1 hydrogen bond forms an S(6) graph-set motif (Bernstein et al., 1995).

In the crystal (Fig. 2), molecules are linked into a one-dimensional chain along the c-axis via intermolecular N2—H1N2···O1 hydrogen bonds (Table 1) and further connected into a two dimensional layer parallel to the bc-plane by intermolecular C9—H9A···F1 hydrogen bonds (Table 1). In addition, a C7—H7A···Cg1 (Table 1) interaction is also observed in the crystal structure (Cg1 is the centroid of C1–C6).

Experimental

An acetone (30 ml) solution of 2-triflouroaniline (1.25 g, 8.4 mmol) was added to a round-bottom flask containing 2,2-diphenylacetyl chloride (1.93 g, 8.4 mmol) and ammonium thiocyanate (0.64 g, 8.4 mmol). The mixture was put at reflux for 1.5 H then filtered off and left to evaporate at room temperature. The colourless precipitate obtained was washed with water and cold ethanol. Colourless crystals suitable for X-ray analysis were obtained by recrystallization of the precipitate in acetone.