Bis(2,3-di-chloro-phen-yl) di-sulfide.

The title compound, C12H6Cl4S2, features an S-S bond [2.0252 (8) Å] that bridges two 2,3-di-chloro-phenyl rings with a C-S-S-C torsion angle of 88.35 (11)°. The benzene rings are normal one to the other with a dihedral angle of 89.83 (11)°. The crystal structure features inter-molecular Cl⋯Cl [3.4763 (11) Å] and π-π stacking inter-actions [centroid-centroid distances = 3.696 (1) and 3.641 (2) Å]. Intra-molecular C-H⋯S inter-actions are also observed.

Related literature

For applications of di­sulfide compounds, see: Crowley (1964 ▶); Hashash et al. (2002 ▶); Gomez-Benitez et al. (2006 ▶); Yu et al. (2010 ▶). For various methods of synthesizing disulfides, see: Xiao et al. (2009 ▶); Shaabani et al. (2008 ▶); Ogilby (2010 ▶). For similar compounds and their crystal structures, see: Deng et al. (2003 ▶); Korp & Bernal (1984 ▶); Tang et al. (2011 ▶). For di­sulfide bonds in proteins, see: Sevier & Kaiser (2006 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C12H6Cl4S2

M = 356.09

Triclinic,

a = 7.7149 (10) Å

b = 7.7326 (11) Å

c = 12.748 (2) Å

α = 91.472 (2)°

β = 91.233 (3)°

γ = 114.859 (2)°

V = 689.37 (18) Å3

Z = 2

Mo Kα radiation

μ = 1.14 mm−1

T = 298 K

0.37 × 0.24 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.678, T max = 0.862

7044 measured reflections

3130 independent reflections

2594 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.03

3130 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814007326/bx2456sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007326/bx2456Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007326/bx2456Isup3.cml

CCDC reference: 994982

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H6Cl4S2	Z = 2
Mr = 356.09	F(000) = 356
Triclinic, P1	Dx = 1.715 Mg m−3
a = 7.7149 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7326 (11) Å	Cell parameters from 4288 reflections
c = 12.748 (2) Å	θ = 2.8–27.5°
α = 91.472 (2)°	µ = 1.14 mm−1
β = 91.233 (3)°	T = 298 K
γ = 114.859 (2)°	Prism, colourless
V = 689.37 (18) Å3	0.37 × 0.24 × 0.14 mm

Bruker SMART APEX CCD diffractometer	3130 independent reflections
Radiation source: fine-focus sealed tube	2594 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.333 pixels mm-1	θmax = 27.5°, θmin = 2.9°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −10→10
Tmin = 0.678, Tmax = 0.862	l = −16→16
7044 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.1749P] where P = (Fo2 + 2Fc2)/3
3130 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.30 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.

	x	y	z	Uiso*/Ueq
Cl1	0.81619 (10)	0.72799 (9)	0.12199 (5)	0.06495 (19)
Cl2	1.23381 (10)	0.95252 (8)	0.04969 (5)	0.0714 (2)
Cl3	0.64782 (10)	−0.26178 (7)	0.37441 (5)	0.06220 (18)
Cl4	0.75120 (11)	−0.22491 (11)	0.61516 (5)	0.0772 (2)
S1	0.67633 (8)	0.32903 (8)	0.20430 (5)	0.05302 (16)
S2	0.64526 (8)	0.07120 (7)	0.25388 (4)	0.05061 (16)
C1	0.9189 (3)	0.4447 (3)	0.16702 (13)	0.0369 (4)
C2	0.9766 (3)	0.6267 (3)	0.12843 (13)	0.0372 (4)
C3	1.1620 (3)	0.7266 (3)	0.09688 (15)	0.0433 (4)
C4	1.2912 (3)	0.6466 (3)	0.10343 (18)	0.0539 (5)
H4	1.4159	0.7138	0.0825	0.065*
C5	1.2338 (3)	0.4663 (3)	0.14126 (18)	0.0548 (5)
H5	1.3207	0.4119	0.1455	0.066*
C6	1.0495 (3)	0.3650 (3)	0.17301 (16)	0.0462 (5)
H6	1.0129	0.2434	0.1984	0.055*
C7	0.7117 (3)	0.1092 (3)	0.39027 (14)	0.0364 (4)
C8	0.7107 (3)	−0.0468 (3)	0.44284 (14)	0.0378 (4)
C9	0.7575 (3)	−0.0306 (3)	0.54892 (16)	0.0447 (5)
C10	0.8069 (3)	0.1407 (4)	0.60354 (17)	0.0564 (6)
H10	0.8395	0.1517	0.6748	0.068*
C11	0.8078 (3)	0.2947 (3)	0.55208 (18)	0.0561 (6)
H11	0.8405	0.4099	0.5891	0.067*
C12	0.7608 (3)	0.2809 (3)	0.44603 (17)	0.0460 (5)
H12	0.7620	0.3864	0.4121	0.055*

	U11	U22	U33	U12	U13	U23
Cl1	0.0859 (4)	0.0712 (4)	0.0671 (4)	0.0592 (3)	0.0296 (3)	0.0276 (3)
Cl2	0.0806 (4)	0.0444 (3)	0.0751 (4)	0.0115 (3)	0.0078 (3)	0.0195 (3)
Cl3	0.0915 (5)	0.0416 (3)	0.0596 (4)	0.0333 (3)	0.0146 (3)	0.0022 (2)
Cl4	0.0910 (5)	0.0889 (5)	0.0677 (4)	0.0512 (4)	0.0099 (3)	0.0389 (3)
S1	0.0447 (3)	0.0628 (3)	0.0570 (3)	0.0262 (3)	0.0104 (2)	0.0284 (3)
S2	0.0609 (3)	0.0430 (3)	0.0377 (3)	0.0117 (2)	−0.0002 (2)	0.0080 (2)
C1	0.0414 (10)	0.0419 (9)	0.0290 (9)	0.0188 (8)	0.0000 (7)	0.0059 (7)
C2	0.0487 (11)	0.0412 (9)	0.0274 (9)	0.0246 (9)	0.0011 (7)	0.0022 (7)
C3	0.0511 (12)	0.0395 (10)	0.0329 (9)	0.0128 (9)	−0.0014 (8)	0.0030 (7)
C4	0.0364 (11)	0.0659 (14)	0.0526 (13)	0.0148 (10)	−0.0018 (9)	0.0069 (11)
C5	0.0465 (12)	0.0707 (14)	0.0576 (13)	0.0348 (11)	−0.0038 (10)	0.0085 (11)
C6	0.0476 (11)	0.0481 (11)	0.0481 (11)	0.0251 (9)	−0.0026 (9)	0.0112 (9)
C7	0.0341 (9)	0.0373 (9)	0.0347 (9)	0.0116 (7)	0.0058 (7)	0.0057 (7)
C8	0.0383 (10)	0.0372 (9)	0.0396 (10)	0.0168 (8)	0.0093 (8)	0.0062 (7)
C9	0.0377 (10)	0.0543 (12)	0.0433 (11)	0.0197 (9)	0.0065 (8)	0.0144 (9)
C10	0.0462 (12)	0.0723 (15)	0.0395 (11)	0.0141 (11)	−0.0012 (9)	0.0010 (10)
C11	0.0520 (13)	0.0469 (12)	0.0547 (13)	0.0070 (10)	0.0028 (10)	−0.0125 (10)
C12	0.0456 (11)	0.0338 (9)	0.0536 (12)	0.0115 (8)	0.0046 (9)	0.0054 (8)

Cl1—C2	1.7224 (19)	C5—C6	1.380 (3)
Cl2—C3	1.725 (2)	C5—H5	0.9300
Cl3—C8	1.7291 (19)	C6—H6	0.9300
Cl4—C9	1.726 (2)	C7—C12	1.389 (3)
S1—C1	1.784 (2)	C7—C8	1.392 (3)
S1—S2	2.0252 (8)	C8—C9	1.381 (3)
S2—C7	1.7834 (19)	C9—C10	1.378 (3)
C1—C6	1.386 (3)	C10—C11	1.372 (3)
C1—C2	1.393 (2)	C10—H10	0.9300
C2—C3	1.384 (3)	C11—C12	1.382 (3)
C3—C4	1.378 (3)	C11—H11	0.9300
C4—C5	1.378 (3)	C12—H12	0.9300
C4—H4	0.9300
C1—S1—S2	105.09 (7)	C1—C6—H6	120.0
C7—S2—S1	105.02 (7)	C12—C7—C8	119.02 (17)
C6—C1—C2	119.06 (18)	C12—C7—S2	124.42 (15)
C6—C1—S1	124.55 (15)	C8—C7—S2	116.55 (14)
C2—C1—S1	116.38 (14)	C9—C8—C7	120.32 (17)
C3—C2—C1	120.36 (18)	C9—C8—Cl3	120.28 (15)
C3—C2—Cl1	120.22 (14)	C7—C8—Cl3	119.39 (14)
C1—C2—Cl1	119.42 (15)	C10—C9—C8	120.27 (19)
C4—C3—C2	120.23 (18)	C10—C9—Cl4	119.19 (17)
C4—C3—Cl2	119.41 (17)	C8—C9—Cl4	120.53 (16)
C2—C3—Cl2	120.36 (16)	C11—C10—C9	119.6 (2)
C5—C4—C3	119.4 (2)	C11—C10—H10	120.2
C5—C4—H4	120.3	C9—C10—H10	120.2
C3—C4—H4	120.3	C10—C11—C12	120.9 (2)
C4—C5—C6	121.0 (2)	C10—C11—H11	119.5
C4—C5—H5	119.5	C12—C11—H11	119.5
C6—C5—H5	119.5	C11—C12—C7	119.85 (19)
C5—C6—C1	119.93 (19)	C11—C12—H12	120.1
C5—C6—H6	120.0	C7—C12—H12	120.1
S2—S1—C1—C6	0.06 (18)	S1—S2—C7—C12	3.60 (18)
S2—S1—C1—C2	179.34 (12)	S1—S2—C7—C8	−177.28 (13)
C6—C1—C2—C3	−0.2 (3)	C12—C7—C8—C9	0.1 (3)
S1—C1—C2—C3	−179.52 (14)	S2—C7—C8—C9	−179.02 (14)
C6—C1—C2—Cl1	−179.31 (14)	C12—C7—C8—Cl3	179.45 (14)
S1—C1—C2—Cl1	1.4 (2)	S2—C7—C8—Cl3	0.3 (2)
C1—C2—C3—C4	0.0 (3)	C7—C8—C9—C10	−0.5 (3)
Cl1—C2—C3—C4	179.07 (16)	Cl3—C8—C9—C10	−179.76 (16)
C1—C2—C3—Cl2	−179.68 (14)	C7—C8—C9—Cl4	178.52 (14)
Cl1—C2—C3—Cl2	−0.6 (2)	Cl3—C8—C9—Cl4	−0.8 (2)
C2—C3—C4—C5	0.3 (3)	C8—C9—C10—C11	0.6 (3)
Cl2—C3—C4—C5	179.91 (17)	Cl4—C9—C10—C11	−178.44 (17)
C3—C4—C5—C6	−0.3 (3)	C9—C10—C11—C12	−0.3 (3)
C4—C5—C6—C1	0.0 (3)	C10—C11—C12—C7	0.0 (3)
C2—C1—C6—C5	0.2 (3)	C8—C7—C12—C11	0.1 (3)
S1—C1—C6—C5	179.46 (16)	S2—C7—C12—C11	179.18 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···S2	0.93	2.70	3.202 (2)	115
C12—H12···S1	0.93	2.70	3.199 (2)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯S2	0.93	2.70	3.202 (2)	115
C12—H12⋯S1	0.93	2.70	3.199 (2)	115