1-{[(Z)-Cyclo­pentyl­idene]amino}-3-phenyl­thio­urea

Joel T Mague; Shaaban K Mohamed; Mehmet Akkurt; Alaa A Hassan; Mustafa R Albayati

doi:10.1107/S1600536814007028

. 2014 Apr 5;70(Pt 5):o515. doi: 10.1107/S1600536814007028

1-{[(Z)-Cyclopentylidene]amino}-3-phenylthiourea

Joel T Mague ^a, Shaaban K Mohamed ^b,^c, Mehmet Akkurt ^d, Alaa A Hassan ^c, Mustafa R Albayati ^e,^*

PMCID: PMC4011296 PMID: 24860330

Abstract

The sample of the title compound, C₁₂H₁₅N₃S, chosen for study consisted of triclinic crystals twinned by a 180° rotation about the a axis. The five-membered ring adopts a twisted conformation. The dihedral angle between the phenyl ring and the mean plane of the thiourea unit is 78.22 (8)°. In the crystal, molecules are linked via pairs of N—H⋯S hydrogen bonds forming inversion dimers.

Related literature

For the use of thiourea as a building-block in the synthesis of heterocycles, see: Yin et al. (2008 ▶). For the diverse biological properties of thiourea-containing compounds and their metal complexes, see: Saeed et al. (2010 ▶); Solomon et al. (2010 ▶); Karakuş & Rollas (2002 ▶); Abdullah & Salh (2010 ▶). For the synthesis of the title compound, see: Akkurt et al. (2014 ▶). For structural studies on thiourea derivatives, see: Struga et al. (2009 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₂H₁₅N₃S
M _r = 233.33
Triclinic,
a = 7.3997 (2) Å
b = 7.5790 (1) Å
c = 11.4657 (2) Å
α = 93.0220 (9)°
β = 105.4530 (9)°
γ = 104.7070 (8)°
V = 594.45 (2) Å³
Z = 2
Cu Kα radiation
μ = 2.21 mm⁻¹
T = 100 K
0.21 × 0.10 × 0.04 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009 ▶) T _min = 0.65, T _max = 0.92
11363 measured reflections
11360 independent reflections
9454 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.097
S = 1.03
11360 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT and CELL_NOW (Sheldrick, 2008a ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008a ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008a ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008a ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814007028/sj5395sup1.cif

e-70-0o515-sup1.cif^{(410.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007028/sj5395Isup2.hkl

e-70-0o515-Isup2.hkl^{(621.9KB, hkl)}

CCDC reference: 994387

Additional supporting information: 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—H2⋯S1ⁱ	0.91	2.56	3.4636 (18)	172

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Symmetry code: (i) Inline graphic .

Acknowledgments

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged.

supplementary crystallographic information

1. Comment

For the past few decades, thiourea derivatives have attracted great attention not only because they are important building blocks in the synthesis of heterocycles and organo-metal complexes (Yin et al., 2008) but also due to their broad spectrum of biological activities such as anti-bacterial, anti-cancer (Saeed et al., 2010), anti-malarial (Solomon et al., 2010), anti-tuberculosis (Karakuş & Rollas 2002) anti-convulsion, analgesic and HDL-elevating properties. In addition, metal complex of thiourea derivatives exhibit anti-inflammatory, anti-cancer and anti-fungal activities (Abdullah & Salh, 2010). Furthermore, the thiourea structure contains a central hydrophilic part and two hydrophobic moieties forming a butterfly-like conformation. This conformation is a part of the structure of an anti-HIV agent (Struga et al., 2009).

Fig. 1 shows a perspective view of the title compound (I). The five-membered ring (C1–C5) adopts a twisted conformation, [the puckering parameters (Cremer & Pople, 1975) are Q(2) = 0.316 (2) Å and φ(2) = 85.7 (4)°]. The dihedral angle between the phenyl ring and the least-squares plane of the thiourea moiety is 78.22 (8)°.

In the crystal structure, the molecules are connected by weak N—H···S interactions (Fig. 2 and Table 1).

2. Experimental

The title compound was prepared according to our previously reported method (Akkurt et al., 2014). Colourless crystals suitable for X-ray diffraction were obtained by crystallization of (I) from ethanol.