2,5-Bis[(3-chloro-benz-yl)sulfan-yl]-1,3,4-thia-diazole.

The complete mol-ecule of the title compound, C(16)H(12)Cl(2)N(2)S(3), is generated by crystallographic twofold symmetry, with the S atom of the thiadiazole ring lying on the rotation axis. The dihedral angle between the mean planes of the 1,3,4-thia-diazole and benzene rings is 87.19 (7)°. In the crystal, mol-ecules are linked by C-H⋯N inter-actions and short S⋯S contacts [3.3389 (9) Å] occur.

Related literature

For details of the synthesis, see: Liu et al. (2012 ▶); Tan et al. (2012 ▶). For a related structure, see: Liu & Liu (2011 ▶. For the biological activity of related compounds, see: Liu et al. (2011a ▶,b ▶).

Experimental

Crystal data

C16H12Cl2N2S3

M = 399.36

Monoclinic,

a = 17.200 (3) Å

b = 5.6604 (11) Å

c = 17.524 (4) Å

β = 92.56 (3)°

V = 1704.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 113 K

0.12 × 0.10 × 0.06 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.916, T max = 0.957

5343 measured reflections

1491 independent reflections

1382 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.063

S = 1.17

1491 reflections

105 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear (Rigaku/MSC, 2005 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812019150/hb6758sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019150/hb6758Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019150/hb6758Isup3.cml

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

C16H12Cl2N2S3	F(000) = 816
Mr = 399.36	Dx = 1.556 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.200 (3) Å	Cell parameters from 2634 reflections
b = 5.6604 (11) Å	θ = 3.3–27.9°
c = 17.524 (4) Å	µ = 0.75 mm−1
β = 92.56 (3)°	T = 113 K
V = 1704.4 (6) Å3	Block, colorless
Z = 4	0.12 × 0.10 × 0.06 mm

Rigaku Saturn CCD diffractometer	1491 independent reflections
Radiation source: rotating anode	1382 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.028
ω scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −20→20
Tmin = 0.916, Tmax = 0.957	k = −6→6
5343 measured reflections	l = −14→20

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0254P)2 + 1.1171P] where P = (Fo2 + 2Fc2)/3
1491 reflections	(Δ/σ)max = 0.001
105 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 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	0.03445 (2)	−0.05340 (7)	0.41412 (2)	0.01769 (13)
S2	0.0000	0.13382 (10)	0.2500	0.01979 (16)
Cl1	0.36343 (2)	−0.14225 (8)	0.42335 (3)	0.03039 (14)
N1	0.01164 (7)	−0.3031 (2)	0.28829 (7)	0.0161 (3)
C1	0.22023 (9)	0.0583 (3)	0.41728 (9)	0.0198 (3)
H1	0.2061	−0.0599	0.4508	0.024*
C2	0.29495 (9)	0.0682 (3)	0.39189 (9)	0.0206 (4)
C3	0.31795 (9)	0.2422 (3)	0.34242 (9)	0.0255 (4)
H3	0.3687	0.2464	0.3263	0.031*
C4	0.26429 (10)	0.4097 (3)	0.31736 (10)	0.0284 (4)
H4	0.2789	0.5278	0.2840	0.034*
C5	0.18844 (10)	0.4023 (3)	0.34188 (9)	0.0232 (4)
H5	0.1525	0.5150	0.3245	0.028*
C6	0.16605 (9)	0.2277 (3)	0.39205 (8)	0.0171 (3)
C7	0.08449 (9)	0.2289 (3)	0.42062 (9)	0.0190 (3)
H7A	0.0540	0.3448	0.3916	0.023*
H7B	0.0869	0.2793	0.4736	0.023*
C8	0.01873 (8)	−0.0905 (3)	0.31589 (8)	0.0136 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0171 (2)	0.0229 (2)	0.0129 (2)	−0.00199 (16)	−0.00114 (15)	0.00075 (15)
S2	0.0314 (3)	0.0127 (3)	0.0149 (3)	0.000	−0.0042 (2)	0.000
Cl1	0.0197 (2)	0.0303 (3)	0.0404 (3)	0.00735 (18)	−0.00680 (18)	0.00062 (19)
N1	0.0158 (6)	0.0171 (7)	0.0153 (6)	−0.0004 (6)	0.0002 (5)	0.0007 (5)
C1	0.0191 (8)	0.0213 (8)	0.0187 (8)	−0.0008 (7)	−0.0024 (6)	−0.0009 (7)
C2	0.0169 (8)	0.0213 (8)	0.0230 (8)	0.0029 (7)	−0.0063 (6)	−0.0050 (7)
C3	0.0143 (8)	0.0314 (10)	0.0308 (9)	−0.0037 (7)	0.0006 (7)	−0.0027 (8)
C4	0.0230 (10)	0.0274 (10)	0.0348 (10)	−0.0044 (8)	0.0018 (7)	0.0074 (8)
C5	0.0198 (9)	0.0204 (9)	0.0289 (9)	0.0020 (7)	−0.0031 (7)	0.0004 (7)
C6	0.0153 (8)	0.0201 (8)	0.0156 (7)	−0.0020 (7)	−0.0030 (6)	−0.0070 (6)
C7	0.0166 (8)	0.0214 (8)	0.0190 (8)	−0.0002 (7)	−0.0009 (6)	−0.0061 (7)
C8	0.0096 (7)	0.0164 (8)	0.0149 (8)	0.0001 (6)	0.0006 (6)	0.0018 (6)

S1—C8	1.7432 (15)	C2—C3	1.382 (2)
S1—C7	1.8161 (17)	C3—C4	1.381 (2)
S2—C8i	1.7367 (15)	C3—H3	0.9300
S2—C8	1.7368 (15)	C4—C5	1.392 (2)
Cl1—C2	1.7471 (17)	C4—H4	0.9300
N1—C8	1.301 (2)	C5—C6	1.389 (2)
N1—N1i	1.383 (2)	C5—H5	0.9300
C1—C2	1.380 (2)	C6—C7	1.511 (2)
C1—C6	1.395 (2)	C7—H7A	0.9700
C1—H1	0.9300	C7—H7B	0.9700
C8—S1—C7	102.72 (7)	C6—C5—C4	120.47 (16)
C8i—S2—C8	86.03 (10)	C6—C5—H5	119.8
C8—N1—N1i	112.28 (8)	C4—C5—H5	119.8
C2—C1—C6	119.25 (15)	C5—C6—C1	119.31 (15)
C2—C1—H1	120.4	C5—C6—C7	119.64 (15)
C6—C1—H1	120.4	C1—C6—C7	121.02 (14)
C1—C2—C3	121.89 (15)	C6—C7—S1	114.82 (11)
C1—C2—Cl1	119.68 (13)	C6—C7—H7A	108.6
C3—C2—Cl1	118.43 (13)	S1—C7—H7A	108.6
C4—C3—C2	118.87 (15)	C6—C7—H7B	108.6
C4—C3—H3	120.6	S1—C7—H7B	108.6
C2—C3—H3	120.6	H7A—C7—H7B	107.5
C3—C4—C5	120.22 (16)	N1—C8—S2	114.69 (11)
C3—C4—H4	119.9	N1—C8—S1	119.12 (11)
C5—C4—H4	119.9	S2—C8—S1	125.76 (9)
C6—C1—C2—C3	0.4 (2)	C5—C6—C7—S1	131.52 (14)
C6—C1—C2—Cl1	179.77 (12)	C1—C6—C7—S1	−50.67 (18)
C1—C2—C3—C4	−0.5 (3)	C8—S1—C7—C6	−69.17 (13)
Cl1—C2—C3—C4	−179.85 (13)	N1i—N1—C8—S2	−1.62 (19)
C2—C3—C4—C5	0.1 (3)	N1i—N1—C8—S1	171.24 (12)
C3—C4—C5—C6	0.4 (3)	C8i—S2—C8—N1	0.62 (7)
C4—C5—C6—C1	−0.5 (2)	C8i—S2—C8—S1	−171.70 (14)
C4—C5—C6—C7	177.37 (15)	C7—S1—C8—N1	154.09 (12)
C2—C1—C6—C5	0.1 (2)	C7—S1—C8—S2	−33.91 (11)
C2—C1—C6—C7	−177.73 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ii	0.93	2.59	3.514 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1i	0.93	2.59	3.514 (2)	172

Symmetry code: (i) .