2-(4-Oxo-3-phenyl-1,3-thia­zolidin-2-yl­idene)malononitrile

Sakka, O.K.; Fleita, D.H.; Harrison, W.T.A.

doi:10.1107/S160053681300216X

Volume 69
Part 3
Page o350
March 2013

Received 16 January 2013
Accepted 22 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.043
wR = 0.086
Data-to-parameter ratio = 13.7
Details

2-(4-Oxo-3-phenyl-1,3-thiazolidin-2-ylidene)malononitrile

Ola K. Sakka,^a ^* Daisy H. Fleita ^a and William T. A. Harrison ^b

^aDepartment of Chemistry, American University in Cairo, PO Box 74, New Cairo 11835, Egypt, and ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
Correspondence e-mail: w.harrison@abdn.ac.uk

In the title compound, C₁₂H₇N₃OS, the essentially planar thiazole ring (r.m.s. deviation = 0.022 Å) forms dihedral angles of 84.88 (9) and 1.8 (3)° with the phenyl ring and the -C(CN)₂ group (r.m.s. deviation = 0.003 Å), respectively. The molecule has approximate local C_s symmetry. In the crystal, molecules are linked via C-HN hydrogen bonds, forming chains propagating along [101]. The crystal studied was found to be an inversion twin with a refined 0.63 (1):0.37 (1) domain ratio.

Related literature

For background to 1,3-thiazolidin-4-ones and their properties, see: Singh et al. (1981); Liesen et al. (2010); Kocabalkanli et al. (2001); Kumar et al. (2007). For further synthetic details, see: Mohareb et al. (2012). For a related structure, see: Pomés Hernández et al. (1996).

Experimental

Crystal data

C₁₂H₇N₃OS
M_r = 241.27
Monoclinic, C c
a = 17.0305 (8) Å
b = 9.5638 (6) Å
c = 7.1651 (4) Å
= 104.199 (4)°
V = 1131.37 (11) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 298 K
0.20 × 0.13 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
2136 measured reflections
2136 independent reflections
1397 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.086
S = 1.01
2136 reflections
156 parameters
2 restraints
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.18 e Å^-3
Absolute structure: Flack (1983), 835 Friedel pairs
Flack parameter: 0.37 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10N2ⁱ	0.93	2.62	3.504 (5)	159
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997), SCALEPACK and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5577 ).

Acknowledgements

The authors would like to thank the American University in Cairo for providing financial support to complete this work.

References

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organic compounds