N-[(2,6-Di­ethyl­phen­yl)carbamo­thio­yl]-2,2-di­phenyl­acetamide

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

doi:10.1107/S1600536813013354

. 2013 May 25;69(Pt 6):o967. doi: 10.1107/S1600536813013354

N-[(2,6-Diethylphenyl)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: PMC3685105 PMID: 23795124

Abstract

In the title compound, C₂₅H₂₆N₂OS, the diethyl-substituted benzene ring forms dihedral angles of 67.38 (9) and 55.32 (9)° with the terminal benzene rings. The molecule adopts a trans–cis conformation with respect to the orientations of the diphenylmethane and 1,3-diethylbenzene groups with respect to the S atom across the C—N bonds. This conformation is stabilized by an intramolecular N—H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, pairs of N—H⋯S hydrogen bonds link the molecules into inversion dimers, forming R ₂ ²(6) loops. The dimer linkage is reinforced by a pair of C—H⋯S hydrogen bonds, which generate R ₂ ²(8) loops. Weak C—H⋯π and π–π [centroid–centroid seperation = 3.8821 (10) Å] interactions also occur in the crystal structure.

Related literature

For related structures and backgroud to thiourea derivatives, 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 ▶).

Experimental

Crystal data

C₂₅H₂₆N₂OS
M _r = 402.54
Triclinic,
a = 8.0091 (1) Å
b = 11.7289 (2) Å
c = 11.8923 (2) Å
α = 79.008 (1)°
β = 80.628 (1)°
γ = 83.936 (1)°
V = 1078.79 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 100 K
0.41 × 0.17 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.934, T _max = 0.987
20294 measured reflections
3767 independent reflections
3123 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.087
S = 1.06
3767 reflections
272 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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

Click here for additional data file.^{(30.2KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013354/hb7080sup1.cif

e-69-0o967-sup1.cif^{(30.2KB, cif)}

Click here for additional data file.^{(184.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013354/hb7080Isup2.hkl

e-69-0o967-Isup2.hkl^{(184.7KB, hkl)}

Click here for additional data file.^{(7.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813013354/hb7080Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1	0.86 (2)	1.96 (2)	2.6702 (19)	140 (2)
N1—H1N1⋯S1ⁱ	0.85 (2)	2.59 (2)	3.4225 (16)	167.4 (18)
C7—H7A⋯S1ⁱ	1.00	2.64	3.6172 (17)	165
C10—H10A⋯Cg1ⁱⁱ	0.95	2.56	3.3859 (19)	146

Open in a new tab

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811151 to conduct this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme Fellowship (ASTS).

supplementary crystallographic information

Comment

As part of our ongoing studies of thiourea derivatives (Yusof et al., 2012a,b), we now describe the structure of the title compound, (I), (Fig. 1).

The bond lengths and angles are comparable to those in related structure (Yusof et al., 2012a,b). The diethyl-substituted benzene ring (C16–C21) forms dihedral angles of 67.38 (9) and 55.32 (9)° with the terminal benzene rings (C1–C6 & C8–C13), respectively. The molecule adopts a trans-cis conformation with respect to the position of diphenylmethane and 1,3-diethylbenzene groups to the sulfur (S1) atom across the C–N bonds, respectively. These configuration further resulting in an S(6) graph-set motif (Bernstein et al., 1995) via intra-molecular N2—H1N2···O1 hydrogen bond (Table 1).

In the crystal (Fig. 2), molecules are linked into dimers via N1—H1N1···S1 and C7—H7A···S1 hydrogen bonds (Table 1), generating R²₂(6) and R²₂(8) loops. C10—H10A···Cg1 (Table 1) interactions and π–π interactions of Cg1···Cg1 = 3.8821 (10) Å (symmetry code: -x, 2-y, 2-z) further stabilized the crystal structure (Cg1 is the centroid of C1–C6).

Experimental

An acetone (30 ml) solution of 2,6-diethylaniline (2.01 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 put at reflux for 2.5 h then filtered off and left to evaporate at room temperature. The colourless precipitate obtained was washed with water and cold ethanol. Colourless plates were obtained by recrystallization of the precipitate from MeOH solution.