Bis(4-amino-2-chloro-phen-yl) disulfide.

The title compound, C(12)H(10)Cl(2)N(2)S(2), features an S-S bond [2.0671 (16) Å] that bridges two 4-amino-2-chloro-phenyl rings with a C-S-S-C torsion angle of -84.2 (2)°. The two benzene rings are twisted with respect to each other at a dihedral angle of 39.9 (2)°. Inter-molecular N-H⋯S hydrogen bonding is present in the crystal structure.

Related literature

For the application of the title compound, see: Crowley (1964 ▶). For S—S bond distances, see: Allen et al. (1991 ▶). For similar C—S—S—C torsion angles in disulfide compounds, see: Korp & Bernal (1984 ▶); Poveteva & Zvonkova (1975 ▶).

Experimental

Crystal data

C12H10Cl2N2S2

M = 317.24

Monoclinic,

a = 6.6360 (13) Å

b = 14.907 (3) Å

c = 13.588 (3) Å

β = 95.09 (3)°

V = 1338.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.78 mm−1

T = 296 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.800, T max = 0.940

2606 measured reflections

1331 independent reflections

1221 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.088

S = 1.00

1331 reflections

163 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 110 Friedel parirs

Flack parameter: 0.09 (11)

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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/S1600536811014425/xu5174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014425/xu5174Isup2.hkl

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

C12H10Cl2N2S2	F(000) = 648
Mr = 317.24	Dx = 1.574 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 25 reflections
a = 6.6360 (13) Å	θ = 10–14°
b = 14.907 (3) Å	µ = 0.78 mm−1
c = 13.588 (3) Å	T = 296 K
β = 95.09 (3)°	Block, yellow
V = 1338.9 (5) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1221 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 25.4°, θmin = 2.7°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = −17→17
Tmin = 0.800, Tmax = 0.940	l = −16→16
2606 measured reflections	3 standard reflections every 200 reflections
1331 independent reflections	intensity decay: 1%

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1331 reflections	Δρmax = 0.19 e Å−3
163 parameters	Δρmin = −0.22 e Å−3
2 restraints	Absolute structure: Flack (1983), 110 Friedel parirs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.09 (11)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.28662 (15)	0.23231 (7)	0.80302 (8)	0.0442 (3)
Cl1	−0.1503 (2)	0.18083 (8)	0.87818 (12)	0.0609 (4)
N1	−0.3017 (9)	0.5116 (3)	0.9000 (3)	0.0681 (14)
H1A	−0.2710	0.5674	0.8950	0.082*
H1B	−0.4135	0.4965	0.9229	0.082*
C1	−0.0811 (7)	0.2917 (3)	0.8603 (3)	0.0380 (9)
Cl2	−0.2000 (2)	0.26890 (7)	0.57856 (11)	0.0586 (4)
S2	0.26156 (17)	0.21357 (8)	0.65170 (9)	0.0441 (3)
N2	−0.3804 (7)	−0.0596 (3)	0.5629 (3)	0.0525 (10)
H2A	−0.3514	−0.1157	0.5684	0.063*
H2B	−0.5012	−0.0431	0.5426	0.063*
C2	−0.2194 (8)	0.3561 (3)	0.8835 (3)	0.0431 (10)
H2C	−0.3415	0.3397	0.9070	0.052*
C3	−0.1716 (8)	0.4459 (3)	0.8708 (3)	0.0453 (11)
C4	0.0098 (8)	0.4693 (3)	0.8332 (3)	0.0455 (11)
H4A	0.0401	0.5292	0.8226	0.055*
C5	0.1417 (8)	0.4043 (3)	0.8121 (3)	0.0425 (10)
H5A	0.2634	0.4208	0.7881	0.051*
C6	0.1012 (6)	0.3126 (3)	0.8252 (3)	0.0358 (9)
C7	0.0675 (7)	0.1343 (3)	0.6287 (3)	0.0364 (9)
C8	0.1075 (7)	0.0430 (3)	0.6402 (3)	0.0418 (10)
H8A	0.2376	0.0250	0.6627	0.050*
C9	−0.0379 (8)	−0.0212 (3)	0.6193 (3)	0.0464 (11)
H9A	−0.0047	−0.0815	0.6277	0.056*
C10	−0.2349 (7)	0.0029 (3)	0.5857 (3)	0.0379 (10)
C11	−0.2776 (7)	0.0940 (3)	0.5730 (3)	0.0371 (9)
H11A	−0.4068	0.1122	0.5490	0.044*
C12	−0.1295 (7)	0.1569 (3)	0.5957 (3)	0.0377 (10)

	U11	U22	U33	U12	U13	U23
S1	0.0341 (6)	0.0425 (6)	0.0543 (6)	0.0054 (5)	−0.0052 (5)	−0.0064 (5)
Cl1	0.0460 (6)	0.0332 (5)	0.1040 (10)	−0.0052 (5)	0.0090 (6)	0.0041 (6)
N1	0.088 (4)	0.049 (2)	0.071 (3)	0.026 (3)	0.027 (3)	0.007 (2)
C1	0.036 (2)	0.031 (2)	0.046 (2)	0.0004 (18)	−0.0038 (19)	−0.0030 (17)
Cl2	0.0485 (7)	0.0276 (5)	0.0974 (10)	0.0017 (5)	−0.0065 (6)	0.0012 (6)
S2	0.0369 (6)	0.0427 (6)	0.0538 (6)	−0.0042 (5)	0.0115 (5)	−0.0047 (5)
N2	0.057 (2)	0.0300 (19)	0.069 (3)	−0.0092 (18)	−0.001 (2)	0.0023 (18)
C2	0.038 (2)	0.044 (2)	0.048 (2)	0.003 (2)	0.0039 (19)	0.003 (2)
C3	0.060 (3)	0.039 (2)	0.036 (2)	0.011 (2)	0.000 (2)	0.0018 (19)
C4	0.065 (3)	0.030 (2)	0.042 (2)	0.002 (2)	0.003 (2)	0.0003 (18)
C5	0.046 (3)	0.041 (2)	0.040 (2)	−0.007 (2)	0.003 (2)	0.0019 (18)
C6	0.030 (2)	0.033 (2)	0.043 (2)	0.0057 (17)	−0.0024 (17)	−0.0062 (16)
C7	0.037 (2)	0.035 (2)	0.038 (2)	0.0007 (18)	0.0072 (17)	−0.0044 (17)
C8	0.036 (2)	0.044 (2)	0.047 (2)	0.012 (2)	0.0091 (19)	0.0015 (19)
C9	0.060 (3)	0.028 (2)	0.051 (3)	0.005 (2)	0.006 (2)	−0.0003 (17)
C10	0.043 (3)	0.036 (2)	0.034 (2)	−0.0029 (18)	0.005 (2)	−0.0024 (17)
C11	0.035 (2)	0.034 (2)	0.042 (2)	−0.0049 (17)	0.0024 (18)	−0.0014 (17)
C12	0.048 (3)	0.0219 (19)	0.043 (2)	0.0055 (19)	0.0043 (19)	−0.0025 (16)

S1—C6	1.762 (4)	C3—C4	1.393 (7)
S1—S2	2.0671 (16)	C4—C5	1.354 (7)
Cl1—C1	1.738 (4)	C4—H4A	0.9300
N1—C3	1.387 (6)	C5—C6	1.407 (6)
N1—H1A	0.8601	C5—H5A	0.9300
N1—H1B	0.8599	C7—C12	1.385 (7)
C1—C6	1.375 (7)	C7—C8	1.393 (6)
C1—C2	1.384 (6)	C8—C9	1.371 (7)
Cl2—C12	1.744 (4)	C8—H8A	0.9300
S2—C7	1.755 (4)	C9—C10	1.393 (7)
N2—C10	1.357 (6)	C9—H9A	0.9300
N2—H2A	0.8599	C10—C11	1.396 (6)
N2—H2B	0.8600	C11—C12	1.374 (7)
C2—C3	1.390 (6)	C11—H11A	0.9300
C2—H2C	0.9300
C6—S1—S2	105.43 (14)	C6—C5—H5A	118.9
C3—N1—H1A	120.2	C1—C6—C5	116.6 (4)
C3—N1—H1B	119.8	C1—C6—S1	123.7 (3)
H1A—N1—H1B	120.0	C5—C6—S1	119.6 (4)
C6—C1—C2	122.9 (4)	C12—C7—C8	116.0 (4)
C6—C1—Cl1	121.0 (3)	C12—C7—S2	123.4 (3)
C2—C1—Cl1	116.1 (4)	C8—C7—S2	120.5 (4)
C7—S2—S1	105.13 (15)	C9—C8—C7	122.4 (4)
C10—N2—H2A	119.9	C9—C8—H8A	118.8
C10—N2—H2B	120.1	C7—C8—H8A	118.8
H2A—N2—H2B	120.0	C8—C9—C10	120.7 (4)
C1—C2—C3	118.5 (5)	C8—C9—H9A	119.7
C1—C2—H2C	120.8	C10—C9—H9A	119.7
C3—C2—H2C	120.8	N2—C10—C9	121.7 (4)
N1—C3—C2	119.4 (5)	N2—C10—C11	120.5 (4)
N1—C3—C4	120.6 (4)	C9—C10—C11	117.8 (4)
C2—C3—C4	120.0 (4)	C12—C11—C10	120.2 (4)
C5—C4—C3	119.7 (4)	C12—C11—H11A	119.9
C5—C4—H4A	120.2	C10—C11—H11A	119.9
C3—C4—H4A	120.2	C11—C12—C7	122.9 (4)
C4—C5—C6	122.3 (5)	C11—C12—Cl2	116.4 (4)
C4—C5—H5A	118.9	C7—C12—Cl2	120.7 (3)
C6—S1—S2—C7	−84.2 (2)	S1—S2—C7—C12	99.7 (4)
C6—C1—C2—C3	−0.1 (7)	S1—S2—C7—C8	−82.5 (3)
Cl1—C1—C2—C3	179.9 (4)	C12—C7—C8—C9	0.6 (6)
C1—C2—C3—N1	−175.6 (4)	S2—C7—C8—C9	−177.4 (3)
C1—C2—C3—C4	1.6 (7)	C7—C8—C9—C10	−0.2 (6)
N1—C3—C4—C5	175.0 (4)	C8—C9—C10—N2	178.8 (4)
C2—C3—C4—C5	−2.1 (7)	C8—C9—C10—C11	0.8 (6)
C3—C4—C5—C6	1.1 (6)	N2—C10—C11—C12	−179.7 (4)
C2—C1—C6—C5	−0.8 (6)	C9—C10—C11—C12	−1.7 (6)
Cl1—C1—C6—C5	179.2 (3)	C10—C11—C12—C7	2.1 (6)
C2—C1—C6—S1	175.6 (3)	C10—C11—C12—Cl2	−179.2 (3)
Cl1—C1—C6—S1	−4.4 (5)	C8—C7—C12—C11	−1.5 (6)
C4—C5—C6—C1	0.3 (6)	S2—C7—C12—C11	176.4 (3)
C4—C5—C6—S1	−176.3 (3)	C8—C7—C12—Cl2	179.8 (3)
S2—S1—C6—C1	102.4 (3)	S2—C7—C12—Cl2	−2.2 (5)
S2—S1—C6—C5	−81.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.80	3.611 (5)	158
N2—H2A···S2ii	0.86	2.86	3.684 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.80	3.611 (5)	158
N2—H2A⋯S2ii	0.86	2.86	3.684 (5)	162

Symmetry codes: (i) ; (ii) .