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In the title compound, (4-O2NC6H4)2S2 or C12H8N2O4S2, the mol­ecules lie across twofold rotation axes. A single type of C-H...O hydrogen bond, with C...O = 3.394 (3) Å and C-H...O = 158°, links the mol­ecules into continuous two-dimensional sheets built from a single type of R44(44) ring. These sheets are linked by aromatic [pi]...[pi] stacking interactions to form a continuous three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100004649/sk1379sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004649/sk1379Isup2.hkl
Contains datablock I

Computing details top

Data collection: KappaCCD Server Software (Enraf-Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Bis-(4-nitrophenyl)disulfide top
Crystal data top
C12H8N2O4S2F(000) = 632
Mr = 308.34Dx = 1.609 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 7.1167 (7) ÅCell parameters from 1411 reflections
b = 14.1692 (15) Åθ = 3.2–27.5°
c = 12.6473 (14) ŵ = 0.43 mm1
β = 93.753 (4)°T = 150 K
V = 1272.6 (2) Å3Plate, yellow
Z = 40.10 × 0.05 × 0.05 mm
Data collection top
KappaCCD
diffractometer
1411 independent reflections
Radiation source: fine-focus sealed X-ray tube1062 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
φ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)
h = 98
Tmin = 0.958, Tmax = 0.979k = 1818
4579 measured reflectionsl = 1516
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0403P)2 + 0.5922P]
where P = (Fo2 + 2Fc2)/3
1411 reflections(Δ/σ)max = 0.001
91 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.36 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.07390 (8)0.19515 (4)0.32141 (4)0.0282 (2)
C10.0343 (3)0.28198 (15)0.39887 (16)0.0243 (5)
C20.0035 (3)0.27414 (16)0.50782 (16)0.0269 (5)
C30.0640 (3)0.34088 (17)0.57459 (17)0.0280 (5)
C40.1712 (3)0.41457 (15)0.53141 (16)0.0265 (5)
N40.2422 (3)0.48575 (14)0.60274 (15)0.0327 (5)
O410.2200 (2)0.47221 (12)0.69860 (13)0.0428 (5)
O420.3195 (3)0.55602 (13)0.56369 (14)0.0444 (5)
C50.2122 (3)0.42328 (16)0.42358 (17)0.0283 (5)
C60.1435 (3)0.35602 (16)0.35704 (17)0.0282 (5)
H20.07600.22260.53610.032*
H30.03760.33650.64900.034*
H50.28620.47450.39570.034*
H60.17090.36040.28270.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0322 (4)0.0280 (3)0.0243 (3)0.0039 (2)0.0002 (2)0.0004 (2)
C10.0244 (11)0.0251 (12)0.0234 (11)0.0041 (9)0.0025 (9)0.0008 (9)
C20.0262 (12)0.0270 (12)0.0273 (11)0.0020 (10)0.0004 (9)0.0029 (10)
C30.0298 (12)0.0316 (12)0.0226 (11)0.0052 (10)0.0008 (9)0.0009 (10)
C40.0295 (12)0.0220 (11)0.0287 (12)0.0049 (9)0.0071 (9)0.0021 (9)
N40.0334 (11)0.0285 (11)0.0371 (12)0.0067 (9)0.0102 (9)0.0065 (9)
O410.0571 (12)0.0412 (11)0.0309 (10)0.0053 (9)0.0099 (8)0.0085 (8)
O420.0508 (11)0.0312 (10)0.0520 (11)0.0093 (8)0.0087 (9)0.0049 (9)
C50.0272 (12)0.0258 (12)0.0323 (12)0.0010 (9)0.0058 (9)0.0053 (10)
C60.0293 (12)0.0307 (13)0.0243 (11)0.0006 (10)0.0013 (9)0.0011 (10)
Geometric parameters (Å, º) top
S1—S1i2.0299 (8)C4—C51.381 (3)
S1—C11.779 (2)C4—N41.465 (3)
C1—C61.389 (3)N4—O411.227 (3)
C1—C21.391 (3)N4—O421.226 (3)
C2—C31.375 (3)C5—C61.382 (3)
C2—H20.9500C5—H50.9500
C3—C41.384 (3)C6—H60.9500
C3—H30.9500
C1—S1—S1i105.80 (7)C5—C4—N4119.2 (2)
C6—C1—C2120.3 (2)C3—C4—N4118.67 (19)
C6—C1—S1124.33 (16)O41—N4—O42123.4 (2)
C2—C1—S1115.31 (16)O41—N4—C4118.2 (2)
C3—C2—C1120.0 (2)O42—N4—C4118.4 (2)
C3—C2—H2120.0C6—C5—C4118.6 (2)
C1—C2—H2120.0C6—C5—H5120.7
C2—C3—C4118.82 (19)C4—C5—H5120.7
C2—C3—H3120.6C5—C6—C1120.0 (2)
C4—C3—H3120.6C5—C6—H6120.0
C5—C4—C3122.2 (2)C1—C6—H6120.0
C1i—S1i—S1—C188.11 (11)C3—C4—N4—O417.2 (3)
S1i—S1—C1—C622.0 (2)C3—C4—N4—O42172.3 (2)
S1i—S1—C1—C2160.6 (15)C5—C4—N4—O41173.1 (2)
C6—C1—C2—C31.3 (3)C3—C4—C5—C60.1 (3)
S1—C1—C2—C3176.15 (16)N4—C4—C5—C6179.62 (19)
C1—C2—C3—C40.8 (3)C4—C5—C6—C10.5 (3)
C2—C3—C4—C50.1 (3)C2—C1—C6—C51.2 (3)
C2—C3—C4—N4179.76 (18)S1—C1—C6—C5176.05 (16)
C5—C4—N4—O427.4 (3)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O42ii0.952.493.394 (3)158
Symmetry code: (ii) x+1/2, y1/2, z.
 

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