(Z)-2-Sulfanyl­idene-5-(thio­phen-2-yl­methyl­idene)imidazolidin-4-one

Abdullah M Asiri; Hassan M Faidallah; Abdulrahman O Al-Youbi; Tarik R Sobahi; Seik Weng Ng

doi:10.1107/S1600536811033034

. 2011 Aug 27;67(Pt 9):o2429. doi: 10.1107/S1600536811033034

(Z)-2-Sulfanylidene-5-(thiophen-2-ylmethylidene)imidazolidin-4-one

Abdullah M Asiri ^a,^b, Hassan M Faidallah ^a, Abdulrahman O Al-Youbi ^a, Tarik R Sobahi ^a, Seik Weng Ng ^c,^a,^*

PMCID: PMC3200739 PMID: 22064773

Abstract

The molecule of the title compound, C₈H₆N₂OS₂, has a V shape with two five-membered rings attached to a methylene C atom. All non-H atoms are approximately coplanar (r.m.s. deviation = 0.096 Å). In the crystal, molecules are linked by N—H⋯O hydrogen bonds into layers. The thiophene ring is disordered over two positions; the major orientation has an occupancy of 0.683 (3). is there an intramolecular N---H...S bond?

Related literature

For two 5-aryl-2-thioxoimidazolin-4-ones, see: Chowdhry et al. (2000 ▶); Książek et al. (2009 ▶).

Experimental

Crystal data

C₈H₆N₂OS₂
M _r = 210.27
Triclinic,
a = 6.1022 (6) Å
b = 7.0806 (8) Å
c = 11.0425 (13) Å
α = 72.582 (11)°
β = 76.116 (10)°
γ = 75.640 (9)°
V = 433.87 (8) Å³
Z = 2
Cu Kα radiation
μ = 5.22 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.356, T _max = 0.903
2599 measured reflections
1677 independent reflections
1519 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.122
S = 1.04
1677 reflections
134 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033034/bt5612sup1.cif

e-67-o2429-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033034/bt5612Isup2.hkl

e-67-o2429-Isup2.hkl^{(82.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033034/bt5612Isup3.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—H2⋯O1ⁱ	0.88	2.20	2.873 (2)	133

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank King Abdulaziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The crystal structures of only a small number of 5-aryl-2-thioxoimidazolidin-4-ones have been reported, with that of the phenyl homolog been described only recently. The bond dimensions of the parent compound are used to explain the nature of the products of its cycloaddition reaction (Książek et al., 2009). The 2-pyridyl derivative is also a flat molecule (Chowdhry et al., 2000) The thienyl analog (Scheme I) is similarly planar (r.m.s. deviation 0.096 Å). The molecule has a somewhat butterfly shape with the two five-membered rings attached to the methylene carbon (Fig. 1). The –NH– unit at the 4-position (of one ring) points towards the S atom in the 2-position (of the other ring); however, the interaction is too weak to lock the molecule so that the thienyl ring is able to adopt two orientations. Two molecules are linked by an N–H···O hydrogen bond across a center-of-inversion to form a dimer.

Experimental

Thiophene-2-carboxaldehyde (1.10 g, 10 mmol) in ethanol (20 ml) was added to a solution of the 2-thiohydantoin (1.16 g,10 mmol) in 20% ethanolic potassium hydroxide (20 ml). The mixture was stirred for 6 h. The mixture was then poured into water (200 ml). The precipitate that separated when this was acidified with 10% hydrochloric acid was collected and recrystallized from ethanol.