2-(4-Oxo-3-phenyl-1,3-thia-zolidin-2-yl-idene)malononitrile.

In the title compound, C12H7N3OS, the essentially planar thia-zole 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 mol-ecule has approximate local Cs symmetry. In the crystal, molecules are linked via C-H⋯N 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 = 241.27

Monoclinic,

a = 17.0305 (8) Å

b = 9.5638 (6) Å

c = 7.1651 (4) Å

β = 104.199 (4)°

V = 1131.37 (11) Å3

Z = 4

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.086

S = 1.01

2136 reflections

156 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 835 Friedel pairs

Flack parameter: 0.37 (1)

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300216X/lh5577sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300216X/lh5577Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300216X/lh5577Isup3.cml

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

C12H7N3OS	F(000) = 496
Mr = 241.27	Dx = 1.416 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1133 reflections
a = 17.0305 (8) Å	θ = 2.9–27.5°
b = 9.5638 (6) Å	µ = 0.27 mm−1
c = 7.1651 (4) Å	T = 298 K
β = 104.199 (4)°	Block, yellow
V = 1131.37 (11) Å3	0.20 × 0.13 × 0.05 mm
Z = 4

Nonius KappaCCD diffractometer	1397 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 27.5°, θmin = 3.6°
ω scans	h = −21→22
2136 measured reflections	k = −12→11
2136 independent reflections	l = −9→9

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0223P)2 + 0.0674P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.17 e Å−3
2136 reflections	Δρmin = −0.18 e Å−3
156 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.008 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 835 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.37 (1)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.40086 (17)	0.3723 (3)	0.3314 (5)	0.0435 (8)
C2	0.31911 (18)	0.3591 (4)	0.3709 (4)	0.0542 (9)
H2A	0.2827	0.3104	0.2657	0.065*
H2B	0.2969	0.4511	0.3830	0.065*
C3	0.43425 (18)	0.2567 (3)	0.6297 (4)	0.0357 (7)
C4	0.48151 (17)	0.1984 (3)	0.7933 (4)	0.0395 (8)
C5	0.4414 (2)	0.1387 (4)	0.9303 (5)	0.0487 (8)
C6	0.5676 (2)	0.1857 (3)	0.8434 (5)	0.0444 (8)
C7	0.54465 (17)	0.3210 (3)	0.4754 (4)	0.0368 (7)
C8	0.58860 (18)	0.4396 (4)	0.5395 (4)	0.0465 (8)
H8	0.5650	0.5143	0.5884	0.056*
C9	0.6685 (2)	0.4455 (5)	0.5297 (5)	0.0669 (11)
H9	0.6994	0.5242	0.5746	0.080*
C10	0.7026 (2)	0.3359 (5)	0.4543 (5)	0.0689 (13)
H10	0.7563	0.3411	0.4470	0.083*
C11	0.6581 (2)	0.2197 (5)	0.3901 (5)	0.0657 (12)
H11	0.6816	0.1456	0.3394	0.079*
C12	0.5784 (2)	0.2111 (4)	0.3998 (4)	0.0534 (10)
H12	0.5480	0.1318	0.3557	0.064*
S1	0.32943 (5)	0.26310 (9)	0.59038 (11)	0.0515 (3)
O1	0.41623 (12)	0.4253 (2)	0.1924 (3)	0.0585 (7)
N1	0.46104 (13)	0.3139 (3)	0.4828 (3)	0.0363 (6)
N2	0.40992 (18)	0.0906 (3)	1.0384 (5)	0.0703 (9)
N3	0.63584 (18)	0.1710 (3)	0.8969 (4)	0.0671 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0331 (18)	0.039 (2)	0.0570 (19)	−0.0008 (15)	0.0092 (15)	−0.0014 (17)
C2	0.036 (2)	0.071 (3)	0.0535 (19)	0.0005 (17)	0.0065 (14)	0.0031 (18)
C3	0.0287 (16)	0.0350 (19)	0.0452 (17)	−0.0036 (15)	0.0126 (13)	−0.0012 (14)
C4	0.0327 (18)	0.042 (2)	0.0459 (19)	0.0010 (14)	0.0142 (15)	0.0074 (15)
C5	0.0362 (19)	0.050 (2)	0.0577 (19)	0.0011 (16)	0.0074 (16)	0.0099 (17)
C6	0.040 (2)	0.048 (2)	0.0461 (17)	−0.0002 (16)	0.0109 (14)	0.0044 (17)
C7	0.0283 (17)	0.045 (2)	0.0386 (17)	−0.0005 (15)	0.0110 (13)	0.0027 (15)
C8	0.042 (2)	0.051 (2)	0.0490 (18)	−0.0055 (17)	0.0144 (14)	−0.0015 (16)
C9	0.047 (2)	0.095 (3)	0.060 (2)	−0.020 (2)	0.0139 (18)	0.007 (2)
C10	0.030 (2)	0.122 (4)	0.057 (2)	0.003 (2)	0.0147 (16)	0.012 (2)
C11	0.046 (2)	0.098 (3)	0.057 (2)	0.026 (2)	0.0199 (19)	0.003 (2)
C12	0.049 (2)	0.057 (3)	0.052 (2)	0.0062 (18)	0.0080 (17)	−0.0045 (15)
S1	0.0288 (4)	0.0603 (6)	0.0661 (5)	−0.0030 (5)	0.0131 (3)	0.0097 (5)
O1	0.0528 (15)	0.0679 (18)	0.0571 (13)	0.0059 (12)	0.0178 (10)	0.0173 (13)
N1	0.0280 (14)	0.0374 (16)	0.0442 (14)	−0.0027 (11)	0.0103 (11)	0.0005 (12)
N2	0.0528 (19)	0.085 (3)	0.076 (2)	−0.0039 (18)	0.0208 (15)	0.030 (2)
N3	0.040 (2)	0.092 (3)	0.067 (2)	0.0083 (17)	0.0091 (15)	0.0192 (18)

C1—O1	1.202 (3)	C7—C12	1.372 (4)
C1—N1	1.412 (4)	C7—C8	1.374 (4)
C1—C2	1.492 (4)	C7—N1	1.439 (3)
C2—S1	1.792 (3)	C8—C9	1.381 (4)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—C10	1.372 (6)
C3—N1	1.361 (4)	C9—H9	0.9300
C3—C4	1.367 (4)	C10—C11	1.361 (5)
C3—S1	1.739 (3)	C10—H10	0.9300
C4—C6	1.426 (4)	C11—C12	1.378 (5)
C4—C5	1.444 (5)	C11—H11	0.9300
C5—N2	1.142 (4)	C12—H12	0.9300
C6—N3	1.140 (4)
O1—C1—N1	122.6 (3)	C7—C8—C9	118.7 (3)
O1—C1—C2	126.5 (3)	C7—C8—H8	120.7
N1—C1—C2	110.9 (3)	C9—C8—H8	120.7
C1—C2—S1	108.3 (2)	C10—C9—C8	120.5 (4)
C1—C2—H2A	110.0	C10—C9—H9	119.8
S1—C2—H2A	110.0	C8—C9—H9	119.8
C1—C2—H2B	110.0	C11—C10—C9	120.1 (4)
S1—C2—H2B	110.0	C11—C10—H10	119.9
H2A—C2—H2B	108.4	C9—C10—H10	119.9
N1—C3—C4	126.1 (3)	C10—C11—C12	120.4 (4)
N1—C3—S1	112.7 (2)	C10—C11—H11	119.8
C4—C3—S1	121.2 (2)	C12—C11—H11	119.8
C3—C4—C6	127.1 (2)	C7—C12—C11	119.2 (4)
C3—C4—C5	117.8 (3)	C7—C12—H12	120.4
C6—C4—C5	115.1 (3)	C11—C12—H12	120.4
N2—C5—C4	179.5 (4)	C3—S1—C2	92.06 (15)
N3—C6—C4	174.6 (3)	C3—N1—C1	115.8 (2)
C12—C7—C8	121.1 (3)	C3—N1—C7	124.7 (2)
C12—C7—N1	119.5 (3)	C1—N1—C7	119.4 (2)
C8—C7—N1	119.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N2i	0.93	2.62	3.504 (5)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯N2i	0.93	2.62	3.504 (5)	159

Symmetry code: (i) .