3-[1-(4-Chloro-phen-yl)eth-yl]-1,3-thia-zinane-2-thione.

In the title compound, C(12)H(14)ClNS(2), the thia-zole ring adopts an envelope conformation; the basal plane is nearly perpendicular to the benzene ring at a dihedral angle of 85.72 (5)°. Weak inter-molecular C-H⋯S hydrogen bonding is present in the crystal structure.

Related literature

For the biological activity of thia­zole compounds, see: Amir et al. (2006 ▶). For a related structure, see: Cunico et al. (2007 ▶).

Experimental

Crystal data

C12H14ClNS2

M = 271.81

Orthorhombic,

a = 11.260 (2) Å

b = 11.888 (2) Å

c = 18.978 (4) Å

V = 2540.5 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.60 mm−1

T = 113 K

0.18 × 0.14 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.900, T max = 0.931

16988 measured reflections

2932 independent reflections

2605 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.089

S = 1.11

2925 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002078/xu5140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002078/xu5140Isup2.hkl

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

C12H14ClNS2	F(000) = 1136
Mr = 271.81	Dx = 1.421 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5973 reflections
a = 11.260 (2) Å	θ = 2.2–27.5°
b = 11.888 (2) Å	µ = 0.60 mm−1
c = 18.978 (4) Å	T = 113 K
V = 2540.5 (9) Å3	Block, colorless
Z = 8	0.18 × 0.14 × 0.12 mm

Rigaku Saturn diffractometer	2932 independent reflections
Radiation source: rotating anode	2605 reflections with I > 2σ(I)
confocal	Rint = 0.050
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −14→14
Tmin = 0.900, Tmax = 0.931	k = −7→15
16988 measured reflections	l = −24→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.9612P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.002
2925 reflections	Δρmax = 0.29 e Å−3
147 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (5)

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
Cl1	−0.02163 (5)	0.84121 (4)	0.54940 (3)	0.03747 (15)
S1	0.12139 (4)	0.46585 (4)	0.16831 (2)	0.02721 (14)
S2	−0.00573 (4)	0.34132 (4)	0.27142 (2)	0.02514 (13)
N1	0.17516 (12)	0.47749 (11)	0.30690 (7)	0.0190 (3)
C1	0.03561 (15)	0.61986 (15)	0.39541 (9)	0.0223 (4)
H1	0.0095	0.6085	0.3495	0.027*
C2	−0.00917 (15)	0.70925 (15)	0.43370 (10)	0.0244 (4)
H2	−0.0652	0.7573	0.4140	0.029*
C3	0.03060 (16)	0.72615 (14)	0.50171 (10)	0.0247 (4)
C4	0.11393 (16)	0.65588 (15)	0.53172 (9)	0.0263 (4)
H4	0.1405	0.6684	0.5774	0.032*
C5	0.15754 (16)	0.56606 (15)	0.49268 (9)	0.0239 (4)
H5	0.2135	0.5183	0.5127	0.029*
C6	0.11905 (14)	0.54630 (13)	0.42412 (9)	0.0191 (3)
C7	0.15969 (15)	0.44518 (14)	0.38191 (9)	0.0211 (4)
H7	0.0951	0.3900	0.3836	0.025*
C8	0.27095 (17)	0.38623 (17)	0.40901 (10)	0.0317 (4)
H8A	0.2939	0.3284	0.3765	0.047*
H8B	0.2548	0.3533	0.4542	0.047*
H8C	0.3342	0.4399	0.4135	0.047*
C9	0.27378 (15)	0.55691 (15)	0.29311 (9)	0.0229 (4)
H9A	0.3458	0.5144	0.2843	0.027*
H9B	0.2868	0.6025	0.3348	0.027*
C10	0.25045 (16)	0.63354 (15)	0.23103 (9)	0.0258 (4)
H10A	0.3144	0.6878	0.2270	0.031*
H10B	0.1771	0.6745	0.2387	0.031*
C11	0.24125 (17)	0.56687 (17)	0.16328 (10)	0.0305 (4)
H11A	0.3155	0.5278	0.1547	0.037*
H11B	0.2273	0.6178	0.1242	0.037*
C12	0.10630 (14)	0.43289 (14)	0.25731 (9)	0.0194 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0465 (3)	0.0281 (3)	0.0379 (3)	0.0064 (2)	0.0101 (2)	−0.0076 (2)
S1	0.0275 (3)	0.0321 (3)	0.0220 (2)	−0.00856 (19)	−0.00050 (18)	−0.00137 (18)
S2	0.0221 (2)	0.0233 (2)	0.0301 (2)	−0.00669 (17)	−0.00089 (18)	−0.00064 (17)
N1	0.0159 (7)	0.0190 (7)	0.0222 (7)	−0.0002 (5)	−0.0002 (6)	−0.0020 (6)
C1	0.0184 (8)	0.0250 (8)	0.0236 (9)	−0.0008 (7)	−0.0032 (7)	−0.0004 (7)
C2	0.0185 (8)	0.0219 (8)	0.0327 (10)	0.0015 (7)	0.0007 (7)	0.0034 (7)
C3	0.0264 (9)	0.0197 (8)	0.0282 (9)	−0.0021 (7)	0.0084 (7)	−0.0006 (7)
C4	0.0304 (10)	0.0293 (9)	0.0192 (8)	−0.0021 (8)	0.0022 (7)	0.0013 (7)
C5	0.0253 (9)	0.0246 (8)	0.0220 (8)	0.0020 (7)	−0.0003 (7)	0.0042 (7)
C6	0.0161 (8)	0.0198 (8)	0.0215 (8)	−0.0023 (6)	0.0012 (7)	0.0028 (7)
C7	0.0213 (9)	0.0204 (8)	0.0215 (8)	−0.0001 (7)	−0.0020 (7)	0.0007 (7)
C8	0.0342 (11)	0.0283 (9)	0.0325 (10)	0.0106 (8)	−0.0070 (8)	−0.0031 (8)
C9	0.0159 (8)	0.0247 (8)	0.0280 (9)	−0.0043 (7)	0.0015 (7)	−0.0042 (7)
C10	0.0214 (9)	0.0206 (8)	0.0353 (10)	−0.0045 (7)	0.0038 (8)	−0.0005 (8)
C11	0.0269 (10)	0.0359 (10)	0.0287 (9)	−0.0090 (8)	0.0034 (8)	0.0026 (8)
C12	0.0172 (8)	0.0158 (7)	0.0253 (8)	0.0024 (6)	−0.0003 (7)	−0.0020 (7)

Cl1—C3	1.7425 (18)	C5—H5	0.9300
S1—C12	1.7422 (18)	C6—C7	1.515 (2)
S1—C11	1.8092 (19)	C7—C8	1.525 (2)
S2—C12	1.6875 (17)	C7—H7	0.9800
N1—C12	1.330 (2)	C8—H8A	0.9600
N1—C9	1.481 (2)	C8—H8B	0.9600
N1—C7	1.485 (2)	C8—H8C	0.9600
C1—C2	1.383 (2)	C9—C10	1.512 (3)
C1—C6	1.394 (2)	C9—H9A	0.9700
C1—H1	0.9300	C9—H9B	0.9700
C2—C3	1.381 (3)	C10—C11	1.514 (3)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.379 (3)	C10—H10B	0.9700
C4—C5	1.389 (2)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.391 (2)
C12—S1—C11	105.85 (8)	C7—C8—H8A	109.5
C12—N1—C9	124.50 (14)	C7—C8—H8B	109.5
C12—N1—C7	120.47 (14)	H8A—C8—H8B	109.5
C9—N1—C7	114.98 (13)	C7—C8—H8C	109.5
C2—C1—C6	121.49 (16)	H8A—C8—H8C	109.5
C2—C1—H1	119.3	H8B—C8—H8C	109.5
C6—C1—H1	119.3	N1—C9—C10	113.05 (14)
C3—C2—C1	119.00 (16)	N1—C9—H9A	109.0
C3—C2—H2	120.5	C10—C9—H9A	109.0
C1—C2—H2	120.5	N1—C9—H9B	109.0
C4—C3—C2	121.23 (16)	C10—C9—H9B	109.0
C4—C3—Cl1	119.37 (15)	H9A—C9—H9B	107.8
C2—C3—Cl1	119.36 (14)	C9—C10—C11	110.98 (15)
C3—C4—C5	119.06 (17)	C9—C10—H10A	109.4
C3—C4—H4	120.5	C11—C10—H10A	109.4
C5—C4—H4	120.5	C9—C10—H10B	109.4
C4—C5—C6	121.22 (16)	C11—C10—H10B	109.4
C4—C5—H5	119.4	H10A—C10—H10B	108.0
C6—C5—H5	119.4	C10—C11—S1	110.72 (12)
C5—C6—C1	117.99 (16)	C10—C11—H11A	109.5
C5—C6—C7	122.29 (15)	S1—C11—H11A	109.5
C1—C6—C7	119.64 (15)	C10—C11—H11B	109.5
N1—C7—C6	109.69 (13)	S1—C11—H11B	109.5
N1—C7—C8	110.24 (14)	H11A—C11—H11B	108.1
C6—C7—C8	115.75 (14)	N1—C12—S2	125.51 (13)
N1—C7—H7	106.9	N1—C12—S1	122.66 (13)
C6—C7—H7	106.9	S2—C12—S1	111.83 (9)
C8—C7—H7	106.9

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···S2i	0.97	2.85	3.773 (2)	158
C10—H10B···S2ii	0.97	2.77	3.701 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯S2i	0.97	2.85	3.773 (2)	158
C10—H10B⋯S2ii	0.97	2.77	3.701 (2)	160

Symmetry codes: (i) ; (ii) .