Bis(4-nitro­phenyl) di­sulfide at 150 K, a three-dimensional framework built from C-H...O hydrogen bonds and aromatic [pi]...[pi] stacking interactions

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.

Computing details

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

Crystal data

C12H8N2O4S2	F(000) = 632
Mr = 308.34	Dx = 1.609 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.1167 (7) Å	Cell parameters from 1411 reflections
b = 14.1692 (15) Å	θ = 3.2–27.5°
c = 12.6473 (14) Å	µ = 0.43 mm^−1
β = 93.753 (4)°	T = 150 K
V = 1272.6 (2) Å^3	Plate, yellow
Z = 4	0.10 × 0.05 × 0.05 mm

Data collection

KappaCCD diffractometer	1411 independent reflections
Radiation source: fine-focus sealed X-ray tube	1062 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −9→8
Tmin = 0.958, Tmax = 0.979	k = −18→18
4579 measured reflections	l = −15→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0403P)^2 + 0.5922P] where P = (Fo^2 + 2Fc^2)/3
1411 reflections	(Δ/σ)max = 0.001
91 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.07390 (8)	0.19515 (4)	0.32141 (4)	0.0282 (2)
C1	−0.0343 (3)	0.28198 (15)	0.39887 (16)	0.0243 (5)
C2	0.0035 (3)	0.27414 (16)	0.50782 (16)	0.0269 (5)
C3	−0.0640 (3)	0.34088 (17)	0.57459 (17)	0.0280 (5)
C4	−0.1712 (3)	0.41457 (15)	0.53141 (16)	0.0265 (5)
N4	−0.2422 (3)	0.48575 (14)	0.60274 (15)	0.0327 (5)
O41	−0.2200 (2)	0.47221 (12)	0.69860 (13)	0.0428 (5)
O42	−0.3195 (3)	0.55602 (13)	0.56369 (14)	0.0444 (5)
C5	−0.2122 (3)	0.42328 (16)	0.42358 (17)	0.0283 (5)
C6	−0.1435 (3)	0.35602 (16)	0.35704 (17)	0.0282 (5)
H2	0.0760	0.2226	0.5361	0.032*
H3	−0.0376	0.3365	0.6490	0.034*
H5	−0.2862	0.4745	0.3957	0.034*
H6	−0.1709	0.3604	0.2827	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0322 (4)	0.0280 (3)	0.0243 (3)	0.0039 (2)	−0.0002 (2)	−0.0004 (2)
C1	0.0244 (11)	0.0251 (12)	0.0234 (11)	−0.0041 (9)	0.0025 (9)	−0.0008 (9)
C2	0.0262 (12)	0.0270 (12)	0.0273 (11)	−0.0020 (10)	0.0004 (9)	0.0029 (10)
C3	0.0298 (12)	0.0316 (12)	0.0226 (11)	−0.0052 (10)	0.0008 (9)	0.0009 (10)
C4	0.0295 (12)	0.0220 (11)	0.0287 (12)	−0.0049 (9)	0.0071 (9)	−0.0021 (9)
N4	0.0334 (11)	0.0285 (11)	0.0371 (12)	−0.0067 (9)	0.0102 (9)	−0.0065 (9)
O41	0.0571 (12)	0.0412 (11)	0.0309 (10)	−0.0053 (9)	0.0099 (8)	−0.0085 (8)
O42	0.0508 (11)	0.0312 (10)	0.0520 (11)	0.0093 (8)	0.0087 (9)	−0.0049 (9)
C5	0.0272 (12)	0.0258 (12)	0.0323 (12)	0.0010 (9)	0.0058 (9)	0.0053 (10)
C6	0.0293 (12)	0.0307 (13)	0.0243 (11)	−0.0006 (10)	0.0013 (9)	0.0011 (10)

Geometric parameters (Å, º)

S1—S1^i	2.0299 (8)	C4—C5	1.381 (3)
S1—C1	1.779 (2)	C4—N4	1.465 (3)
C1—C6	1.389 (3)	N4—O41	1.227 (3)
C1—C2	1.391 (3)	N4—O42	1.226 (3)
C2—C3	1.375 (3)	C5—C6	1.382 (3)
C2—H2	0.9500	C5—H5	0.9500
C3—C4	1.384 (3)	C6—H6	0.9500
C3—H3	0.9500
C1—S1—S1^i	105.80 (7)	C5—C4—N4	119.2 (2)
C6—C1—C2	120.3 (2)	C3—C4—N4	118.67 (19)
C6—C1—S1	124.33 (16)	O41—N4—O42	123.4 (2)
C2—C1—S1	115.31 (16)	O41—N4—C4	118.2 (2)
C3—C2—C1	120.0 (2)	O42—N4—C4	118.4 (2)
C3—C2—H2	120.0	C6—C5—C4	118.6 (2)
C1—C2—H2	120.0	C6—C5—H5	120.7
C2—C3—C4	118.82 (19)	C4—C5—H5	120.7
C2—C3—H3	120.6	C5—C6—C1	120.0 (2)
C4—C3—H3	120.6	C5—C6—H6	120.0
C5—C4—C3	122.2 (2)	C1—C6—H6	120.0
C1^i—S1^i—S1—C1	88.11 (11)	C3—C4—N4—O41	−7.2 (3)
S1^i—S1—C1—C6	−22.0 (2)	C3—C4—N4—O42	172.3 (2)
S1^i—S1—C1—C2	160.6 (15)	C5—C4—N4—O41	173.1 (2)
C6—C1—C2—C3	−1.3 (3)	C3—C4—C5—C6	−0.1 (3)
S1—C1—C2—C3	176.15 (16)	N4—C4—C5—C6	179.62 (19)
C1—C2—C3—C4	0.8 (3)	C4—C5—C6—C1	−0.5 (3)
C2—C3—C4—C5	−0.1 (3)	C2—C1—C6—C5	1.2 (3)
C2—C3—C4—N4	−179.76 (18)	S1—C1—C6—C5	−176.05 (16)
C5—C4—N4—O42	−7.4 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O42^ii	0.95	2.49	3.394 (3)	158

Symmetry code: (ii) x+1/2, y−1/2, z.