N-[(3-Ethyl­phen­yl)carbamo­thio­yl]-2,2-di­phenyl­acetamide

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

doi:10.1107/S1600536813014268

. 2013 Jun 8;69(Pt 7):o1016–o1017. doi: 10.1107/S1600536813014268

N-[(3-Ethylphenyl)carbamothioyl]-2,2-diphenylacetamide

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

PMCID: PMC3772456 PMID: 24046599

Abstract

In the title molecule, C₂₃H₂₂N₂OS, the diphenylacetyl and ethylbenzene groups adopt a trans–cis conformation, respectively, with respect to the S atom across the (S=)C—N bonds. This conformation is stabilized by an intramolecular N—H⋯O hydrogen bond and a weak C—H⋯S hydrogen bond. The ethyl-substituted benzene ring forms dihedral angles of 87.53 (15) and 73.94 (15)° with the phenyl rings. In the crystal, N—H⋯O hydrogen bonds link molecules into chains along [100]. A weak C—H⋯π interaction is also observed.

Related literature

For the biological activity of carbonylthiourea derivatives, see: Zhong et al. (2008 ▶); Saeed et al. (2010 ▶). For related structures, see: Yusof et al. (2012a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For standard bond lenths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₃H₂₂N₂OS
M _r = 374.49
Orthorhombic,
a = 10.0608 (2) Å
b = 17.9092 (5) Å
c = 10.8495 (3) Å
V = 1954.87 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.26 × 0.23 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.955, T _max = 0.983
11560 measured reflections
4121 independent reflections
2885 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.098
S = 0.99
4121 reflections
253 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ▶), 1761 Friedel pairs
Flack parameter: 0.17 (9)

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/S1600536813014268/lh5616sup1.cif

e-69-o1016-sup1.cif^{(28.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014268/lh5616Isup2.hkl

e-69-o1016-Isup2.hkl^{(202KB, hkl)}

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

Supplementary material file. DOI: 10.1107/S1600536813014268/lh5616Isup3.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
N2—H1N2⋯O1	0.90 (3)	1.82 (3)	2.630 (3)	148 (3)
C21—H21A⋯S1	0.95	2.61	3.255 (3)	126
N1—H1N1⋯O1ⁱ	0.82 (3)	2.25 (3)	3.023 (3)	157 (3)
C7—H7A⋯Cg ⁱⁱ	1.00	2.87	3.844 (3)	166

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

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

Carbonylthiourea derivatives have been explored because they are reported to posses biological activities such as antibacterial, anti-fungal and antiviral (Zhong et al., 2008; Saeed et al., 2010). The crystal structure of the title compound is presented herein.

The molecular structure is shown in Fig. 1. The diphenylacetyl and ethylbenzene groups adopt a trans-cis configuration, respectively, with respect to the sulfur atom across the (S═)C–N bonds. Intramolecular N2—H1N2···O1 and C21—H21A···S1 hydrogen bonds result in two S(6) graph-set motifs (Bernstein et al., 1995). The ethyl-substituted benzene ring (C16–C21) forms dihedral angles of 87.53 (15) and 73.94 (15)°, respectively with the C1–C6 and C8–C13 rings. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to related structures (Yusof et al., 2012a,b).

In the crystal molecules are linked into one-dimensional chains along the [100] via intermolecular N1—H1N1···O16ⁱ hydrogen bonds (Table 1). In addition, a weak C7—H7A···Cgⁱⁱ interaction is observed (Cg is the centroid of C8–C13).

Experimental

An acetone (30 ml) solution of 3-ethylaniline (1.63 g, 13.5 mmol) was added to a round-bottom flask containing 2,2-diphenylacetyl chloride (3.10 g, 13.5 mmol) and ammonium thiocyanate (1.03 g, 13.5 mmol). The mixture was refluxed for 2.5h 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 DMSO.