1,2-Bis(2,4-di-nitro-phen-yl)disulfane.

In the title mol-ecule, C12H6N4O8S2, the dihedral angle between the benzene rings is 77.00 (8)°. The mean planes of the nitro groups are twisted slightly from the benzene rings, forming dihedral angles in the range 2.3 (2)-8.6 (3)°. The S-S bond length is 2.0458 (7) Å. Each S atom is essentially coplanar with the benzene ring to which it is attached, with deviations from the ring planes of 0.0163 (5) and 0.0538 (5) Å. In the crystal, mol-ecules are linked through weak C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (001).

Related literature

For synthetic applications of di­sulfides, see: Khavasch et al. (1950 ▶); Mitin & Zaperalova (1974 ▶); Stepanov et al. (1974 ▶, 1977 ▶); Cochran et al. (1996 ▶). For the natural occurrence of di­sulfides, see: Ramadas & Srinivasan (1995 ▶). For the preparation procedures for di­sulfides, see: Khavasch & Cameron (1951 ▶); Traynelis & Rieck (1973 ▶); Bilozor & Boldyrev (1984 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For related structures, see: Glidewell et al. (2000 ▶); Song & Fan (2009 ▶); Xiao et al. (2010 ▶); Buvaneswari et al. (2012 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H6N4O8S2

M = 398.33

Monoclinic,

a = 11.3776 (6) Å

b = 11.9579 (5) Å

c = 11.0459 (6) Å

β = 90.943 (2)°

V = 1502.62 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.804, T max = 0.922

22589 measured reflections

5706 independent reflections

3983 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.141

S = 1.02

5706 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011082/lh5606sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011082/lh5606Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011082/lh5606Isup3.cml

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

C12H6N4O8S2	F(000) = 808
Mr = 398.33	Dx = 1.761 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7792 reflections
a = 11.3776 (6) Å	θ = 2.5–30.2°
b = 11.9579 (5) Å	µ = 0.41 mm−1
c = 11.0459 (6) Å	T = 293 K
β = 90.943 (2)°	Block, yellow
V = 1502.62 (13) Å3	0.25 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	5706 independent reflections
Radiation source: fine-focus sealed tube	3983 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scan	θmax = 33.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −17→16
Tmin = 0.804, Tmax = 0.922	k = −17→18
22589 measured reflections	l = −16→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.4377P] where P = (Fo2 + 2Fc2)/3
5706 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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
C1	0.94644 (14)	0.13448 (15)	0.26049 (15)	0.0423 (3)
C2	0.87515 (16)	0.21656 (14)	0.21366 (17)	0.0459 (4)
H2	0.8704	0.2863	0.2504	0.055*
C3	0.81090 (15)	0.19244 (13)	0.11069 (16)	0.0414 (3)
C4	0.81370 (13)	0.08818 (12)	0.05402 (14)	0.0360 (3)
C5	0.88741 (14)	0.00751 (13)	0.10614 (15)	0.0402 (3)
H5	0.8917	−0.0631	0.0711	0.048*
C6	0.95385 (14)	0.03052 (14)	0.20845 (16)	0.0423 (3)
H6	1.0032	−0.0237	0.2419	0.051*
C7	0.56165 (13)	−0.32356 (13)	0.13396 (14)	0.0357 (3)
C8	0.62734 (13)	−0.37316 (13)	0.04595 (15)	0.0386 (3)
H8	0.6302	−0.4505	0.0380	0.046*
C9	0.68881 (13)	−0.30433 (13)	−0.03018 (14)	0.0358 (3)
C10	0.68625 (12)	−0.18758 (13)	−0.02111 (13)	0.0342 (3)
C11	0.61794 (14)	−0.14233 (13)	0.07059 (15)	0.0391 (3)
H11	0.6145	−0.0651	0.0798	0.047*
C12	0.55557 (14)	−0.20961 (13)	0.14776 (15)	0.0385 (3)
H12	0.5101	−0.1784	0.2082	0.046*
N1	1.01562 (15)	0.15860 (17)	0.37076 (16)	0.0594 (4)
N2	0.73842 (17)	0.28314 (13)	0.06113 (19)	0.0586 (4)
N3	0.49685 (13)	−0.39543 (13)	0.21674 (14)	0.0477 (3)
N4	0.75847 (13)	−0.36018 (14)	−0.12208 (14)	0.0476 (3)
O1	1.08349 (18)	0.0867 (2)	0.40606 (18)	0.0917 (6)
O2	1.00333 (17)	0.24936 (18)	0.41926 (17)	0.0815 (5)
O3	0.7298 (2)	0.36795 (16)	0.1202 (2)	0.1180 (9)
O4	0.69201 (16)	0.26986 (13)	−0.03687 (19)	0.0752 (5)
O5	0.44650 (15)	−0.35239 (14)	0.30093 (15)	0.0700 (4)
O6	0.49935 (17)	−0.49559 (13)	0.19861 (18)	0.0799 (5)
O7	0.75453 (16)	−0.46121 (13)	−0.12824 (17)	0.0778 (5)
O8	0.81704 (14)	−0.30190 (14)	−0.18852 (14)	0.0655 (4)
S1	0.72498 (4)	0.05824 (4)	−0.07550 (4)	0.04737 (13)
S2	0.76812 (4)	−0.10241 (4)	−0.12039 (4)	0.04554 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0357 (7)	0.0502 (9)	0.0413 (8)	−0.0104 (6)	0.0067 (6)	−0.0055 (7)
C2	0.0488 (9)	0.0382 (8)	0.0513 (9)	−0.0065 (7)	0.0143 (7)	−0.0080 (7)
C3	0.0412 (8)	0.0335 (7)	0.0499 (9)	−0.0008 (6)	0.0103 (7)	0.0043 (6)
C4	0.0359 (7)	0.0335 (7)	0.0390 (7)	−0.0070 (5)	0.0064 (6)	0.0041 (5)
C5	0.0407 (8)	0.0332 (7)	0.0467 (8)	−0.0027 (6)	0.0038 (6)	−0.0013 (6)
C6	0.0356 (7)	0.0427 (8)	0.0487 (9)	−0.0013 (6)	0.0020 (6)	0.0029 (7)
C7	0.0326 (7)	0.0360 (7)	0.0384 (7)	−0.0004 (5)	0.0012 (5)	0.0030 (5)
C8	0.0381 (7)	0.0320 (6)	0.0458 (8)	0.0035 (5)	−0.0016 (6)	−0.0028 (6)
C9	0.0325 (7)	0.0387 (7)	0.0360 (7)	0.0036 (5)	0.0004 (5)	−0.0076 (6)
C10	0.0318 (6)	0.0378 (7)	0.0331 (6)	−0.0037 (5)	0.0009 (5)	−0.0017 (5)
C11	0.0427 (8)	0.0309 (6)	0.0440 (8)	−0.0003 (6)	0.0077 (6)	−0.0032 (6)
C12	0.0383 (7)	0.0362 (7)	0.0414 (8)	0.0024 (6)	0.0097 (6)	−0.0032 (6)
N1	0.0498 (9)	0.0760 (12)	0.0524 (9)	−0.0147 (8)	−0.0006 (7)	−0.0107 (8)
N2	0.0671 (11)	0.0374 (8)	0.0714 (11)	0.0071 (7)	0.0062 (9)	0.0083 (7)
N3	0.0443 (8)	0.0449 (8)	0.0540 (9)	−0.0049 (6)	0.0050 (6)	0.0119 (6)
N4	0.0445 (8)	0.0499 (8)	0.0485 (8)	0.0045 (6)	0.0063 (6)	−0.0146 (6)
O1	0.0865 (13)	0.1028 (15)	0.0845 (13)	0.0076 (11)	−0.0384 (10)	−0.0111 (11)
O2	0.0828 (12)	0.0917 (12)	0.0701 (11)	−0.0154 (10)	0.0018 (9)	−0.0382 (9)
O3	0.196 (3)	0.0589 (11)	0.0986 (15)	0.0615 (14)	−0.0184 (16)	−0.0123 (10)
O4	0.0770 (11)	0.0504 (8)	0.0972 (13)	0.0045 (7)	−0.0282 (10)	0.0116 (8)
O5	0.0730 (10)	0.0733 (10)	0.0646 (9)	−0.0068 (8)	0.0304 (8)	0.0071 (8)
O6	0.0989 (13)	0.0415 (7)	0.1001 (13)	−0.0095 (8)	0.0274 (10)	0.0162 (8)
O7	0.0914 (12)	0.0486 (8)	0.0946 (13)	0.0047 (8)	0.0382 (10)	−0.0246 (8)
O8	0.0707 (9)	0.0673 (9)	0.0594 (8)	−0.0052 (7)	0.0297 (7)	−0.0162 (7)
S1	0.0535 (3)	0.0414 (2)	0.0469 (2)	−0.00851 (17)	−0.00634 (18)	0.00949 (16)
S2	0.0508 (2)	0.0483 (2)	0.0377 (2)	−0.01204 (17)	0.00926 (16)	−0.00253 (16)

C1—C2	1.369 (3)	C9—C10	1.400 (2)
C1—C6	1.373 (2)	C9—N4	1.460 (2)
C1—N1	1.468 (2)	C10—C11	1.396 (2)
C2—C3	1.373 (3)	C10—S2	1.7723 (15)
C2—H2	0.9300	C11—C12	1.378 (2)
C3—C4	1.396 (2)	C11—H11	0.9300
C3—N2	1.463 (2)	C12—H12	0.9300
C4—C5	1.396 (2)	N1—O1	1.216 (3)
C4—S1	1.7738 (16)	N1—O2	1.219 (3)
C5—C6	1.377 (2)	N2—O4	1.207 (3)
C5—H5	0.9300	N2—O3	1.211 (3)
C6—H6	0.9300	N3—O5	1.215 (2)
C7—C8	1.371 (2)	N3—O6	1.215 (2)
C7—C12	1.373 (2)	N4—O7	1.211 (2)
C7—N3	1.463 (2)	N4—O8	1.218 (2)
C8—C9	1.376 (2)	S1—S2	2.0458 (7)
C8—H8	0.9300
C2—C1—C6	122.07 (16)	C8—C9—N4	116.01 (14)
C2—C1—N1	118.61 (17)	C10—C9—N4	121.21 (14)
C6—C1—N1	119.31 (17)	C11—C10—C9	116.81 (13)
C1—C2—C3	117.81 (15)	C11—C10—S2	122.06 (12)
C1—C2—H2	121.1	C9—C10—S2	121.13 (11)
C3—C2—H2	121.1	C12—C11—C10	121.42 (14)
C2—C3—C4	122.93 (15)	C12—C11—H11	119.3
C2—C3—N2	116.33 (16)	C10—C11—H11	119.3
C4—C3—N2	120.74 (16)	C7—C12—C11	118.92 (14)
C3—C4—C5	116.76 (15)	C7—C12—H12	120.5
C3—C4—S1	121.68 (12)	C11—C12—H12	120.5
C5—C4—S1	121.54 (12)	O1—N1—O2	124.45 (19)
C6—C5—C4	121.21 (15)	O1—N1—C1	117.14 (19)
C6—C5—H5	119.4	O2—N1—C1	118.4 (2)
C4—C5—H5	119.4	O4—N2—O3	123.72 (19)
C1—C6—C5	119.21 (16)	O4—N2—C3	118.27 (17)
C1—C6—H6	120.4	O3—N2—C3	118.0 (2)
C5—C6—H6	120.4	O5—N3—O6	123.81 (17)
C8—C7—C12	122.49 (14)	O5—N3—C7	118.59 (15)
C8—C7—N3	118.38 (14)	O6—N3—C7	117.57 (16)
C12—C7—N3	119.13 (14)	O7—N4—O8	123.85 (16)
C7—C8—C9	117.59 (14)	O7—N4—C9	118.39 (16)
C7—C8—H8	121.2	O8—N4—C9	117.76 (15)
C9—C8—H8	121.2	C4—S1—S2	104.44 (6)
C8—C9—C10	122.78 (14)	C10—S2—S1	105.01 (5)
C6—C1—C2—C3	−0.7 (3)	N3—C7—C12—C11	179.17 (14)
N1—C1—C2—C3	−179.85 (15)	C10—C11—C12—C7	0.3 (2)
C1—C2—C3—C4	1.3 (2)	C2—C1—N1—O1	−175.60 (19)
C1—C2—C3—N2	−178.22 (15)	C6—C1—N1—O1	5.2 (3)
C2—C3—C4—C5	−0.9 (2)	C2—C1—N1—O2	2.9 (3)
N2—C3—C4—C5	178.56 (15)	C6—C1—N1—O2	−176.26 (18)
C2—C3—C4—S1	177.43 (13)	C2—C3—N2—O4	171.12 (18)
N2—C3—C4—S1	−3.1 (2)	C4—C3—N2—O4	−8.4 (3)
C3—C4—C5—C6	0.0 (2)	C2—C3—N2—O3	−7.9 (3)
S1—C4—C5—C6	−178.38 (12)	C4—C3—N2—O3	172.6 (2)
C2—C1—C6—C5	−0.2 (3)	C8—C7—N3—O5	173.98 (16)
N1—C1—C6—C5	178.95 (15)	C12—C7—N3—O5	−5.4 (2)
C4—C5—C6—C1	0.6 (2)	C8—C7—N3—O6	−4.1 (2)
C12—C7—C8—C9	0.1 (2)	C12—C7—N3—O6	176.51 (17)
N3—C7—C8—C9	−179.24 (13)	C8—C9—N4—O7	2.6 (2)
C7—C8—C9—C10	−0.2 (2)	C10—C9—N4—O7	−177.71 (17)
C7—C8—C9—N4	179.53 (14)	C8—C9—N4—O8	−177.67 (16)
C8—C9—C10—C11	0.3 (2)	C10—C9—N4—O8	2.1 (2)
N4—C9—C10—C11	−179.36 (14)	C3—C4—S1—S2	178.71 (12)
C8—C9—C10—S2	179.38 (12)	C5—C4—S1—S2	−3.03 (14)
N4—C9—C10—S2	−0.3 (2)	C11—C10—S2—S1	−4.57 (14)
C9—C10—C11—C12	−0.4 (2)	C9—C10—S2—S1	176.45 (11)
S2—C10—C11—C12	−179.43 (13)	C4—S1—S2—C10	80.78 (7)
C8—C7—C12—C11	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.54	3.341 (3)	144
C8—H8···O3ii	0.93	2.60	3.403 (2)	144
C12—H12···O6iii	0.93	2.42	3.139 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.54	3.341 (3)	144
C8—H8⋯O3ii	0.93	2.60	3.403 (2)	144
C12—H12⋯O6iii	0.93	2.42	3.139 (2)	134

Symmetry codes: (i) ; (ii) ; (iii) .