1,2-Bis(2-nitro-phen-yl)disulfane.

In the title compound, C(12)H(8)N(2)O(4)S(2), the dihedral angle between the two benzene rings is 67.82 (9)°. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For background to disulfides, see: Kitamura et al. (1991 ▶); Palmer et al. (1995 ▶); Ramadas & Srinivasan (1995 ▶). For related structures, see: Glidewell et al. (2000 ▶);

Experimental

Crystal data

C12H8N2O4S2

M = 308.32

Monoclinic,

a = 8.3762 (9) Å

b = 21.028 (2) Å

c = 8.1011 (10) Å

β = 111.768 (1)°

V = 1325.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 298 K

0.44 × 0.18 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.838, T max = 0.948

6598 measured reflections

2317 independent reflections

1507 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.117

S = 0.92

2317 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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/S1600536809042780/bq2169sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042780/bq2169Isup2.hkl

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

C12H8N2O4S2	F(000) = 632
Mr = 308.32	Dx = 1.545 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1601 reflections
a = 8.3762 (9) Å	θ = 2.6–24.7°
b = 21.028 (2) Å	µ = 0.42 mm−1
c = 8.1011 (10) Å	T = 298 K
β = 111.768 (1)°	Needle, yellow
V = 1325.1 (3) Å3	0.44 × 0.18 × 0.13 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2317 independent reflections
Radiation source: fine-focus sealed tube	1507 reflections with I > 2σ(I)
graphite	Rint = 0.045
phi and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.838, Tmax = 0.948	k = −25→20
6598 measured reflections	l = −9→9

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0627P)2] where P = (Fo2 + 2Fc2)/3
2317 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.16 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	0.09105 (9)	0.26719 (4)	0.07988 (11)	0.0597 (3)
S2	0.01195 (10)	0.35209 (4)	−0.05162 (11)	0.0621 (3)
N1	0.3638 (4)	0.16520 (13)	0.2840 (4)	0.0692 (8)
N2	−0.2348 (3)	0.46767 (13)	−0.1758 (4)	0.0619 (7)
O1	0.2185 (3)	0.15373 (11)	0.1813 (4)	0.0830 (7)
O2	0.4683 (4)	0.12365 (13)	0.3492 (5)	0.1297 (13)
O3	−0.1569 (3)	0.44411 (12)	−0.2595 (3)	0.0852 (7)
O4	−0.3526 (4)	0.50494 (12)	−0.2385 (4)	0.0995 (9)
C1	0.3037 (3)	0.28110 (13)	0.2387 (4)	0.0473 (7)
C2	0.4143 (4)	0.23134 (13)	0.3261 (4)	0.0531 (8)
C3	0.5754 (4)	0.24239 (16)	0.4559 (5)	0.0685 (9)
H3	0.6454	0.2084	0.5124	0.082*
C4	0.6305 (4)	0.30339 (18)	0.5001 (5)	0.0779 (10)
H4	0.7382	0.3112	0.5869	0.093*
C5	0.5255 (4)	0.35347 (16)	0.4151 (5)	0.0719 (10)
H5	0.5631	0.3950	0.4448	0.086*
C6	0.3655 (4)	0.34241 (14)	0.2866 (4)	0.0594 (8)
H6	0.2972	0.3768	0.2305	0.071*
C7	−0.0762 (3)	0.39748 (13)	0.0814 (4)	0.0485 (7)
C8	−0.1831 (3)	0.44971 (13)	0.0136 (4)	0.0494 (7)
C9	−0.2478 (4)	0.48675 (15)	0.1161 (5)	0.0633 (9)
H9	−0.3200	0.5209	0.0660	0.076*
C10	−0.2036 (4)	0.47214 (17)	0.2937 (5)	0.0714 (10)
H10	−0.2442	0.4969	0.3649	0.086*
C11	−0.0996 (4)	0.42093 (16)	0.3642 (4)	0.0671 (9)
H11	−0.0699	0.4113	0.4839	0.081*
C12	−0.0371 (3)	0.38288 (15)	0.2607 (4)	0.0550 (8)
H12	0.0307	0.3477	0.3109	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0511 (4)	0.0572 (5)	0.0614 (6)	−0.0011 (4)	0.0099 (4)	−0.0114 (4)
S2	0.0619 (5)	0.0762 (6)	0.0455 (5)	0.0124 (4)	0.0167 (4)	−0.0020 (4)
N1	0.0631 (18)	0.0618 (18)	0.083 (2)	0.0056 (16)	0.0281 (17)	0.0059 (16)
N2	0.0582 (16)	0.0521 (17)	0.064 (2)	−0.0038 (13)	0.0096 (15)	0.0000 (15)
O1	0.0839 (18)	0.0626 (16)	0.093 (2)	−0.0072 (13)	0.0213 (16)	−0.0079 (13)
O2	0.097 (2)	0.0610 (17)	0.201 (4)	0.0235 (16)	0.020 (2)	0.026 (2)
O3	0.0949 (18)	0.106 (2)	0.0536 (15)	0.0135 (16)	0.0258 (14)	0.0114 (14)
O4	0.111 (2)	0.0818 (18)	0.086 (2)	0.0278 (17)	0.0132 (16)	0.0264 (15)
C1	0.0420 (15)	0.0549 (18)	0.0471 (18)	0.0003 (14)	0.0192 (13)	−0.0036 (14)
C2	0.0537 (17)	0.0514 (18)	0.059 (2)	0.0004 (14)	0.0272 (16)	0.0023 (15)
C3	0.0526 (18)	0.075 (2)	0.071 (2)	0.0103 (17)	0.0154 (17)	0.0117 (19)
C4	0.0493 (19)	0.087 (3)	0.082 (3)	−0.0052 (19)	0.0056 (18)	−0.003 (2)
C5	0.0541 (19)	0.068 (2)	0.084 (3)	−0.0084 (18)	0.0146 (18)	−0.009 (2)
C6	0.0504 (17)	0.0541 (19)	0.071 (2)	0.0010 (15)	0.0194 (16)	−0.0010 (16)
C7	0.0401 (14)	0.0565 (18)	0.0460 (18)	−0.0034 (13)	0.0126 (13)	−0.0048 (14)
C8	0.0443 (15)	0.0472 (17)	0.0504 (19)	−0.0073 (13)	0.0103 (14)	−0.0015 (14)
C9	0.0589 (19)	0.056 (2)	0.072 (3)	−0.0018 (15)	0.0210 (18)	−0.0066 (17)
C10	0.072 (2)	0.075 (2)	0.073 (3)	0.0013 (19)	0.034 (2)	−0.021 (2)
C11	0.066 (2)	0.085 (2)	0.053 (2)	0.0054 (19)	0.0263 (17)	−0.0023 (18)
C12	0.0516 (17)	0.066 (2)	0.0468 (19)	0.0048 (15)	0.0179 (15)	0.0018 (15)

S1—C1	1.793 (3)	C4—H4	0.9300
S1—S2	2.0584 (12)	C5—C6	1.378 (4)
S2—C7	1.791 (3)	C5—H5	0.9300
N1—O2	1.210 (3)	C6—H6	0.9300
N1—O1	1.217 (3)	C7—C8	1.395 (4)
N1—C2	1.457 (4)	C7—C12	1.399 (4)
N2—O3	1.208 (3)	C8—C9	1.388 (4)
N2—O4	1.214 (3)	C9—C10	1.380 (5)
N2—C8	1.480 (4)	C9—H9	0.9300
C1—C6	1.390 (4)	C10—C11	1.370 (5)
C1—C2	1.403 (4)	C10—H10	0.9300
C2—C3	1.389 (4)	C11—C12	1.394 (4)
C3—C4	1.365 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.381 (4)
C1—S1—S2	105.87 (10)	C4—C5—H5	119.7
C7—S2—S1	106.03 (11)	C5—C6—C1	121.6 (3)
O2—N1—O1	122.2 (3)	C5—C6—H6	119.2
O2—N1—C2	119.1 (3)	C1—C6—H6	119.2
O1—N1—C2	118.6 (3)	C8—C7—C12	116.8 (3)
O3—N2—O4	123.7 (3)	C8—C7—S2	122.0 (2)
O3—N2—C8	117.7 (3)	C12—C7—S2	121.2 (2)
O4—N2—C8	118.6 (3)	C9—C8—C7	122.8 (3)
C6—C1—C2	116.3 (3)	C9—C8—N2	116.6 (3)
C6—C1—S1	121.3 (2)	C7—C8—N2	120.5 (3)
C2—C1—S1	122.3 (2)	C10—C9—C8	119.0 (3)
C3—C2—C1	122.1 (3)	C10—C9—H9	120.5
C3—C2—N1	116.9 (3)	C8—C9—H9	120.5
C1—C2—N1	120.9 (3)	C11—C10—C9	119.5 (3)
C4—C3—C2	119.7 (3)	C11—C10—H10	120.2
C4—C3—H3	120.2	C9—C10—H10	120.2
C2—C3—H3	120.2	C10—C11—C12	121.6 (3)
C3—C4—C5	119.6 (3)	C10—C11—H11	119.2
C3—C4—H4	120.2	C12—C11—H11	119.2
C5—C4—H4	120.2	C11—C12—C7	120.2 (3)
C6—C5—C4	120.6 (3)	C11—C12—H12	119.9
C6—C5—H5	119.7	C7—C12—H12	119.9

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4i	0.93	2.53	3.231 (4)	133
C11—H11···O3ii	0.93	2.54	3.293 (4)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O4i	0.93	2.53	3.231 (4)	133
C11—H11⋯O3ii	0.93	2.54	3.293 (4)	138

Symmetry codes: (i) ; (ii) .