2-{3-[1-(3,4-Dichloro-phen-yl)eth-yl]-1,3-thia-zolidin-2-yl-idene}malononitrile.

In the title compound, C(14)H(11)Cl(2)N(3)S, the thia-zole ring is in an envelope conformation with the -CH(2)- group bonded to the S atom forming the flap. The crystal structure is stabilized by weak inter-molecular C-H⋯Cl and C-H⋯N hydrogen bonds.

Related literature

For the biological activity of thia­zole componds, see: Hense et al. (2002 ▶). For the synthesis of the title compound, see: Jeschke et al. (2002 ▶). For a related structure, see: Cunico, et al. (2007 ▶).

Experimental

Crystal data

C14H11Cl2N3S

M = 324.22

Monoclinic,

a = 7.5900 (15) Å

b = 14.957 (3) Å

c = 12.783 (3) Å

β = 99.03 (3)°

V = 1433.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 113 K

0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.922, T max = 0.943

8837 measured reflections

2493 independent reflections

2374 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.102

S = 1.17

2493 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024049/lh5066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024049/lh5066Isup2.hkl

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

C14H11Cl2N3S	F(000) = 664
Mr = 324.22	Dx = 1.503 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3119 reflections
a = 7.5900 (15) Å	θ = 2.1–27.2°
b = 14.957 (3) Å	µ = 0.59 mm−1
c = 12.783 (3) Å	T = 113 K
β = 99.03 (3)°	Prism, black
V = 1433.2 (5) Å3	0.14 × 0.12 × 0.10 mm
Z = 4

Rigaku Saturn diffractometer	2493 independent reflections
Radiation source: fine-focus sealed tube	2374 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.7°
ω scans	h = −9→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
Tmin = 0.922, Tmax = 0.943	l = −15→13
8837 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0287P)2 + 2.7247P] where P = (Fo2 + 2Fc2)/3
2493 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.98 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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
S1	0.64889 (9)	0.08386 (5)	−0.14263 (5)	0.01840 (19)
Cl1	0.92712 (10)	0.58799 (5)	0.13883 (6)	0.0241 (2)
Cl2	0.74727 (10)	0.62951 (5)	−0.09604 (6)	0.0243 (2)
N1	0.7016 (3)	0.19511 (15)	0.01236 (18)	0.0156 (5)
N2	0.2888 (3)	0.16439 (17)	0.1598 (2)	0.0228 (6)
N3	0.1985 (3)	0.01685 (18)	−0.1358 (2)	0.0276 (6)
C1	0.5784 (4)	0.13843 (17)	−0.0353 (2)	0.0146 (6)
C2	0.8768 (4)	0.1872 (2)	−0.0228 (2)	0.0194 (6)
H2A	0.9508	0.1414	0.0192	0.023*
H2B	0.9410	0.2450	−0.0150	0.023*
C3	0.8370 (4)	0.1601 (2)	−0.1382 (2)	0.0199 (6)
H3A	0.9408	0.1297	−0.1607	0.024*
H3B	0.8047	0.2127	−0.1843	0.024*
C4	0.4095 (4)	0.11831 (18)	−0.0098 (2)	0.0161 (6)
C5	0.3460 (4)	0.14437 (18)	0.0850 (2)	0.0174 (6)
C6	0.2938 (4)	0.06174 (19)	−0.0798 (2)	0.0184 (6)
C7	0.6790 (4)	0.26246 (19)	0.0927 (2)	0.0177 (6)
H7A	0.5539	0.2575	0.1076	0.021*
C8	0.8041 (4)	0.2423 (2)	0.1955 (2)	0.0242 (7)
H8A	0.7885	0.1800	0.2160	0.036*
H8B	0.7762	0.2821	0.2516	0.036*
H8C	0.9279	0.2518	0.1850	0.036*
C9	0.6999 (4)	0.35513 (18)	0.0458 (2)	0.0158 (6)
C10	0.7943 (4)	0.42212 (19)	0.1048 (2)	0.0178 (6)
H10A	0.8506	0.4103	0.1752	0.021*
C11	0.8072 (4)	0.50688 (18)	0.0613 (2)	0.0173 (6)
C12	0.7274 (4)	0.52438 (19)	−0.0414 (2)	0.0187 (6)
C13	0.6305 (4)	0.45847 (19)	−0.1013 (2)	0.0197 (6)
H13A	0.5743	0.4708	−0.1716	0.024*
C14	0.6165 (4)	0.37428 (19)	−0.0575 (2)	0.0186 (6)
H14A	0.5494	0.3291	−0.0981	0.022*

	U11	U22	U33	U12	U13	U23
S1	0.0204 (4)	0.0169 (4)	0.0180 (4)	0.0004 (3)	0.0032 (3)	−0.0022 (3)
Cl1	0.0280 (4)	0.0179 (4)	0.0271 (4)	−0.0050 (3)	0.0062 (3)	−0.0057 (3)
Cl2	0.0257 (4)	0.0176 (4)	0.0315 (4)	0.0026 (3)	0.0111 (3)	0.0080 (3)
N1	0.0142 (12)	0.0136 (12)	0.0192 (12)	−0.0005 (9)	0.0035 (9)	0.0004 (9)
N2	0.0222 (13)	0.0214 (13)	0.0257 (14)	−0.0027 (10)	0.0068 (11)	0.0004 (11)
N3	0.0236 (14)	0.0267 (15)	0.0314 (15)	−0.0036 (11)	0.0010 (12)	−0.0027 (12)
C1	0.0171 (14)	0.0111 (13)	0.0149 (13)	0.0047 (10)	0.0002 (11)	0.0030 (10)
C2	0.0134 (14)	0.0202 (15)	0.0250 (15)	−0.0009 (11)	0.0038 (11)	−0.0006 (12)
C3	0.0170 (14)	0.0221 (15)	0.0217 (15)	−0.0002 (12)	0.0063 (12)	0.0011 (12)
C4	0.0170 (14)	0.0119 (13)	0.0183 (14)	−0.0010 (11)	−0.0005 (11)	0.0021 (11)
C5	0.0141 (14)	0.0124 (14)	0.0248 (16)	0.0001 (10)	0.0001 (12)	0.0037 (12)
C6	0.0177 (14)	0.0183 (15)	0.0198 (15)	0.0008 (12)	0.0047 (12)	0.0037 (12)
C7	0.0170 (14)	0.0177 (15)	0.0193 (15)	−0.0024 (11)	0.0061 (11)	−0.0039 (11)
C8	0.0330 (17)	0.0201 (15)	0.0191 (15)	−0.0044 (13)	0.0032 (13)	0.0022 (12)
C9	0.0137 (13)	0.0135 (14)	0.0213 (15)	−0.0006 (10)	0.0058 (11)	−0.0005 (11)
C10	0.0168 (14)	0.0203 (15)	0.0174 (14)	0.0020 (11)	0.0059 (11)	−0.0023 (11)
C11	0.0151 (14)	0.0128 (14)	0.0255 (15)	−0.0006 (11)	0.0074 (11)	−0.0044 (11)
C12	0.0186 (14)	0.0162 (14)	0.0232 (15)	0.0030 (11)	0.0095 (12)	0.0035 (12)
C13	0.0178 (14)	0.0222 (15)	0.0195 (15)	0.0039 (12)	0.0040 (11)	0.0016 (12)
C14	0.0149 (14)	0.0186 (15)	0.0219 (15)	−0.0018 (11)	0.0019 (11)	−0.0032 (12)

S1—C1	1.751 (3)	C4—C6	1.429 (4)
S1—C3	1.821 (3)	C7—C8	1.526 (4)
Cl1—C11	1.732 (3)	C7—C9	1.528 (4)
Cl2—C12	1.736 (3)	C7—H7A	1.0000
N1—C1	1.336 (3)	C8—H8A	0.9800
N1—C7	1.468 (3)	C8—H8B	0.9800
N1—C2	1.474 (4)	C8—H8C	0.9800
N2—C5	1.150 (4)	C9—C10	1.384 (4)
N3—C6	1.151 (4)	C9—C14	1.402 (4)
C1—C4	1.404 (4)	C10—C11	1.394 (4)
C2—C3	1.514 (4)	C10—H10A	0.9500
C2—H2A	0.9900	C11—C12	1.382 (4)
C2—H2B	0.9900	C12—C13	1.386 (4)
C3—H3A	0.9900	C13—C14	1.389 (4)
C3—H3B	0.9900	C13—H13A	0.9500
C4—C5	1.427 (4)	C14—H14A	0.9500
C1—S1—C3	91.05 (13)	N1—C7—H7A	107.6
C1—N1—C7	127.2 (2)	C8—C7—H7A	107.6
C1—N1—C2	114.2 (2)	C9—C7—H7A	107.6
C7—N1—C2	118.6 (2)	C7—C8—H8A	109.5
N1—C1—C4	129.0 (3)	C7—C8—H8B	109.5
N1—C1—S1	112.0 (2)	H8A—C8—H8B	109.5
C4—C1—S1	119.0 (2)	C7—C8—H8C	109.5
N1—C2—C3	105.5 (2)	H8A—C8—H8C	109.5
N1—C2—H2A	110.6	H8B—C8—H8C	109.5
C3—C2—H2A	110.6	C10—C9—C14	118.9 (3)
N1—C2—H2B	110.6	C10—C9—C7	121.3 (2)
C3—C2—H2B	110.6	C14—C9—C7	119.7 (2)
H2A—C2—H2B	108.8	C9—C10—C11	120.3 (3)
C2—C3—S1	103.50 (19)	C9—C10—H10A	119.9
C2—C3—H3A	111.1	C11—C10—H10A	119.9
S1—C3—H3A	111.1	C12—C11—C10	120.2 (3)
C2—C3—H3B	111.1	C12—C11—Cl1	121.6 (2)
S1—C3—H3B	111.1	C10—C11—Cl1	118.2 (2)
H3A—C3—H3B	109.0	C11—C12—C13	120.3 (3)
C1—C4—C5	125.5 (2)	C11—C12—Cl2	120.0 (2)
C1—C4—C6	118.4 (3)	C13—C12—Cl2	119.6 (2)
C5—C4—C6	115.9 (2)	C12—C13—C14	119.3 (3)
N2—C5—C4	177.5 (3)	C12—C13—H13A	120.3
N3—C6—C4	179.0 (3)	C14—C13—H13A	120.3
N1—C7—C8	110.0 (2)	C13—C14—C9	120.9 (3)
N1—C7—C9	108.5 (2)	C13—C14—H14A	119.6
C8—C7—C9	115.4 (2)	C9—C14—H14A	119.6
C7—N1—C1—C4	−11.5 (4)	C1—N1—C7—C9	−114.5 (3)
C2—N1—C1—C4	169.1 (3)	C2—N1—C7—C9	64.9 (3)
C7—N1—C1—S1	169.1 (2)	N1—C7—C9—C10	−138.4 (3)
C2—N1—C1—S1	−10.3 (3)	C8—C7—C9—C10	−14.5 (4)
C3—S1—C1—N1	−11.7 (2)	N1—C7—C9—C14	44.2 (3)
C3—S1—C1—C4	168.8 (2)	C8—C7—C9—C14	168.0 (3)
C1—N1—C2—C3	32.4 (3)	C14—C9—C10—C11	−0.6 (4)
C7—N1—C2—C3	−147.1 (2)	C7—C9—C10—C11	−178.1 (2)
N1—C2—C3—S1	−37.5 (2)	C9—C10—C11—C12	−0.7 (4)
C1—S1—C3—C2	28.5 (2)	C9—C10—C11—Cl1	−180.0 (2)
N1—C1—C4—C5	−11.2 (5)	C10—C11—C12—C13	1.5 (4)
S1—C1—C4—C5	168.2 (2)	Cl1—C11—C12—C13	−179.3 (2)
N1—C1—C4—C6	173.6 (3)	C10—C11—C12—Cl2	−178.8 (2)
S1—C1—C4—C6	−7.0 (3)	Cl1—C11—C12—Cl2	0.4 (3)
C1—C4—C5—N2	169 (7)	C11—C12—C13—C14	−0.9 (4)
C6—C4—C5—N2	−16 (7)	Cl2—C12—C13—C14	179.4 (2)
C1—C4—C6—N3	−147 (20)	C12—C13—C14—C9	−0.5 (4)
C5—C4—C6—N3	37 (20)	C10—C9—C14—C13	1.2 (4)
C1—N1—C7—C8	118.5 (3)	C7—C9—C14—C13	178.8 (3)
C2—N1—C7—C8	−62.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N3i	0.99	2.57	3.477 (4)	153
C7—H7A···Cl2ii	1.00	2.83	3.623 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯N3i	0.99	2.57	3.477 (4)	153
C7—H7A⋯Cl2ii	1.00	2.83	3.623 (3)	137

Symmetry codes: (i) ; (ii) .