Bis(2,4-dinitro-phen-yl)sulfane.

In the title compound, C(12)H(6)N(4)O(8)S, the dinitro-phenyl rings subtend an angle of 78.46 (13) °. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds leading to the formation of a two-dimensional network lying parallel to the bc plane.

Related literature

For applications of bis­(2,4-dinitro­phen­yl)sulfane, see: Nakadate et al. (1964 ▶); Alekhina et al. (1978 ▶); Parihar et al. (1971 ▶); Evans & Kinnard (1983 ▶); Andricopulo et al. (2006 ▶). For related syntheses, see: Pesin et al. (1963 ▶); Joshi & Mathur (1963 ▶); Obata et al. (1966 ▶); Stepanov et al. (1974 ▶); Davydov & Beletskaya (2003 ▶). For our previous work to synthesize new substituted barbiturates, see: Manickkam & Kalaivani (2011 ▶); Rajamani & Kalaivani (2012 ▶).

Experimental

Crystal data

C12H6N4O8S

M = 366.27

Monoclinic,

a = 9.9428 (12) Å

b = 7.3693 (9) Å

c = 19.743 (2) Å

β = 95.525 (8)°

V = 1439.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 296 K

0.15 × 0.06 × 0.03 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.958, T max = 0.991

15342 measured reflections

2949 independent reflections

1651 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.110

S = 0.99

2949 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

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

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041803/su2502sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041803/su2502Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041803/su2502Isup3.cml

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

C12H6N4O8S	F(000) = 744
Mr = 366.27	Dx = 1.690 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 687 reflections
a = 9.9428 (12) Å	θ = 2.5–26.0°
b = 7.3693 (9) Å	µ = 0.28 mm−1
c = 19.743 (2) Å	T = 296 K
β = 95.525 (8)°	Needle, yellow
V = 1439.9 (3) Å3	0.15 × 0.06 × 0.03 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2949 independent reflections
Radiation source: fine-focus sealed tube	1651 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→12
Tmin = 0.958, Tmax = 0.991	k = −9→9
15342 measured reflections	l = −24→24

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) = 0.110	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0462P)2] where P = (Fo2 + 2Fc2)/3
2949 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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	0.45894 (8)	0.54204 (10)	0.14730 (4)	0.0467 (3)
O1	0.3487 (3)	0.3356 (3)	0.26264 (12)	0.0808 (10)
O2	0.4165 (2)	0.4985 (3)	0.35003 (11)	0.0765 (10)
O3	0.0912 (3)	1.0117 (4)	0.35223 (14)	0.0914 (11)
O4	0.0607 (3)	1.1747 (4)	0.26196 (14)	0.0947 (11)
O5	−0.0437 (3)	0.1541 (3)	−0.05028 (11)	0.0740 (10)
O6	0.1255 (3)	0.0405 (4)	−0.09656 (12)	0.0925 (11)
O7	0.5752 (2)	0.1785 (3)	−0.00808 (11)	0.0684 (9)
O8	0.6174 (2)	0.3770 (3)	0.07036 (11)	0.0624 (8)
N1	0.3628 (3)	0.4798 (3)	0.29238 (13)	0.0520 (10)
N2	0.1077 (3)	1.0440 (4)	0.29312 (16)	0.0599 (11)
N3	0.0775 (3)	0.1350 (4)	−0.05396 (13)	0.0611 (10)
N4	0.5382 (3)	0.2847 (3)	0.03373 (12)	0.0459 (9)
C1	0.3436 (3)	0.6771 (3)	0.18964 (13)	0.0367 (9)
C2	0.3140 (3)	0.6456 (3)	0.25585 (13)	0.0368 (9)
C3	0.2394 (3)	0.7630 (4)	0.29087 (13)	0.0423 (10)
C4	0.1913 (3)	0.9165 (4)	0.25738 (14)	0.0401 (10)
C5	0.2169 (3)	0.9557 (4)	0.19209 (14)	0.0449 (10)
C6	0.2941 (3)	0.8364 (4)	0.15892 (13)	0.0440 (10)
C7	0.3467 (3)	0.4152 (3)	0.09096 (12)	0.0371 (9)
C8	0.2065 (3)	0.4231 (3)	0.09266 (13)	0.0441 (10)
C9	0.1189 (3)	0.3318 (4)	0.04641 (14)	0.0477 (10)
C10	0.1710 (3)	0.2295 (4)	−0.00390 (13)	0.0447 (10)
C11	0.3068 (3)	0.2136 (3)	−0.00716 (13)	0.0465 (10)
C12	0.3938 (3)	0.3044 (3)	0.04037 (12)	0.0382 (9)
H3	0.22210	0.73970	0.33550	0.0510*
H5	0.18280	1.06060	0.17070	0.0540*
H6	0.31380	0.86290	0.11490	0.0530*
H8	0.17140	0.49230	0.12620	0.0530*
H9	0.02610	0.33860	0.04880	0.0570*
H11	0.34050	0.14300	−0.04070	0.0560*

	U11	U22	U33	U12	U13	U23
S1	0.0398 (5)	0.0482 (4)	0.0514 (5)	0.0035 (4)	0.0003 (4)	−0.0120 (3)
O1	0.103 (2)	0.0390 (13)	0.0968 (18)	−0.0003 (13)	−0.0090 (15)	0.0069 (12)
O2	0.0911 (19)	0.0906 (18)	0.0463 (14)	0.0343 (15)	−0.0016 (13)	0.0164 (12)
O3	0.099 (2)	0.103 (2)	0.0792 (18)	0.0258 (16)	0.0441 (16)	−0.0093 (15)
O4	0.088 (2)	0.0925 (19)	0.103 (2)	0.0568 (17)	0.0064 (16)	−0.0047 (16)
O5	0.0647 (18)	0.0820 (17)	0.0701 (16)	−0.0079 (15)	−0.0199 (14)	−0.0082 (12)
O6	0.101 (2)	0.0974 (19)	0.0755 (17)	0.0002 (17)	−0.0092 (15)	−0.0459 (15)
O7	0.0732 (17)	0.0770 (15)	0.0579 (14)	0.0166 (13)	0.0215 (12)	−0.0157 (12)
O8	0.0480 (14)	0.0682 (14)	0.0712 (15)	0.0035 (12)	0.0067 (12)	−0.0111 (12)
N1	0.0514 (17)	0.0513 (17)	0.0532 (17)	0.0087 (13)	0.0042 (14)	0.0107 (13)
N2	0.0426 (17)	0.0652 (18)	0.072 (2)	0.0118 (15)	0.0060 (15)	−0.0144 (16)
N3	0.072 (2)	0.0569 (17)	0.0512 (17)	−0.0049 (17)	−0.0103 (17)	−0.0068 (13)
N4	0.0543 (18)	0.0448 (14)	0.0394 (14)	0.0080 (13)	0.0084 (13)	0.0055 (11)
C1	0.0345 (17)	0.0352 (15)	0.0391 (16)	0.0006 (13)	−0.0030 (13)	−0.0044 (12)
C2	0.0331 (17)	0.0365 (14)	0.0396 (16)	−0.0003 (13)	−0.0033 (13)	0.0030 (12)
C3	0.0343 (17)	0.0539 (17)	0.0385 (16)	−0.0014 (14)	0.0031 (13)	−0.0004 (13)
C4	0.0292 (17)	0.0413 (16)	0.0493 (18)	0.0016 (13)	0.0019 (13)	−0.0092 (13)
C5	0.0441 (18)	0.0392 (15)	0.0500 (18)	0.0066 (15)	−0.0022 (14)	0.0027 (14)
C6	0.0494 (19)	0.0464 (16)	0.0365 (15)	0.0015 (15)	0.0064 (14)	0.0037 (13)
C7	0.0417 (18)	0.0343 (14)	0.0351 (15)	0.0016 (13)	0.0030 (13)	0.0008 (11)
C8	0.046 (2)	0.0450 (17)	0.0411 (16)	0.0004 (14)	0.0040 (14)	−0.0065 (13)
C9	0.0437 (19)	0.0457 (17)	0.0527 (18)	0.0012 (15)	−0.0007 (15)	−0.0013 (14)
C10	0.055 (2)	0.0404 (16)	0.0364 (16)	−0.0002 (15)	−0.0079 (15)	−0.0013 (13)
C11	0.063 (2)	0.0386 (16)	0.0371 (16)	0.0079 (16)	0.0003 (15)	−0.0010 (13)
C12	0.0444 (19)	0.0350 (14)	0.0353 (15)	0.0048 (13)	0.0047 (14)	0.0047 (12)

S1—C1	1.786 (3)	C2—C3	1.370 (4)
S1—C7	1.766 (3)	C3—C4	1.373 (4)
O1—N1	1.216 (3)	C4—C5	1.369 (4)
O2—N1	1.218 (3)	C5—C6	1.374 (4)
O3—N2	1.218 (4)	C7—C8	1.399 (4)
O4—N2	1.212 (4)	C7—C12	1.405 (3)
O5—N3	1.222 (4)	C8—C9	1.376 (4)
O6—N3	1.224 (4)	C9—C10	1.387 (4)
O7—N4	1.220 (3)	C10—C11	1.363 (4)
O8—N4	1.223 (3)	C11—C12	1.386 (4)
N1—C2	1.477 (3)	C3—H3	0.9300
N2—C4	1.478 (4)	C5—H5	0.9300
N3—C10	1.466 (4)	C6—H6	0.9300
N4—C12	1.462 (4)	C8—H8	0.9300
C1—C2	1.387 (4)	C9—H9	0.9300
C1—C6	1.390 (4)	C11—H11	0.9300
C1—S1—C7	101.22 (13)	S1—C7—C8	122.26 (19)
O1—N1—O2	124.8 (3)	S1—C7—C12	121.5 (2)
O1—N1—C2	118.0 (2)	C8—C7—C12	116.3 (2)
O2—N1—C2	117.2 (2)	C7—C8—C9	122.2 (2)
O3—N2—O4	124.1 (3)	C8—C9—C10	119.0 (3)
O3—N2—C4	117.9 (3)	N3—C10—C9	119.0 (3)
O4—N2—C4	118.0 (3)	N3—C10—C11	119.6 (2)
O5—N3—O6	123.9 (3)	C9—C10—C11	121.4 (3)
O5—N3—C10	118.0 (3)	C10—C11—C12	118.9 (2)
O6—N3—C10	118.0 (3)	N4—C12—C7	121.3 (2)
O7—N4—O8	122.6 (3)	N4—C12—C11	116.5 (2)
O7—N4—C12	119.2 (2)	C7—C12—C11	122.2 (3)
O8—N4—C12	118.3 (2)	C2—C3—H3	121.00
S1—C1—C2	123.51 (19)	C4—C3—H3	121.00
S1—C1—C6	118.9 (2)	C4—C5—H5	121.00
C2—C1—C6	117.0 (2)	C6—C5—H5	121.00
N1—C2—C1	120.6 (2)	C1—C6—H6	119.00
N1—C2—C3	116.4 (2)	C5—C6—H6	119.00
C1—C2—C3	123.0 (2)	C7—C8—H8	119.00
C2—C3—C4	117.3 (2)	C9—C8—H8	119.00
N2—C4—C3	118.7 (3)	C8—C9—H9	121.00
N2—C4—C5	118.7 (3)	C10—C9—H9	120.00
C3—C4—C5	122.7 (3)	C10—C11—H11	121.00
C4—C5—C6	118.5 (3)	C12—C11—H11	121.00
C1—C6—C5	121.6 (2)
C7—S1—C1—C2	105.6 (2)	C6—C1—C2—C3	0.1 (4)
C7—S1—C1—C6	−83.5 (2)	S1—C1—C6—C5	−172.9 (2)
C1—S1—C7—C8	−6.2 (2)	C2—C1—C6—C5	−1.3 (4)
C1—S1—C7—C12	171.83 (19)	N1—C2—C3—C4	−179.0 (3)
O1—N1—C2—C1	−46.5 (4)	C1—C2—C3—C4	1.0 (4)
O1—N1—C2—C3	133.5 (3)	C2—C3—C4—N2	178.6 (3)
O2—N1—C2—C1	132.4 (3)	C2—C3—C4—C5	−1.0 (4)
O2—N1—C2—C3	−47.7 (4)	N2—C4—C5—C6	−179.7 (3)
O3—N2—C4—C3	3.8 (4)	C3—C4—C5—C6	−0.1 (5)
O3—N2—C4—C5	−176.6 (3)	C4—C5—C6—C1	1.3 (4)
O4—N2—C4—C3	−176.7 (3)	S1—C7—C8—C9	176.4 (2)
O4—N2—C4—C5	2.9 (4)	C12—C7—C8—C9	−1.7 (4)
O5—N3—C10—C9	1.8 (4)	S1—C7—C12—N4	2.1 (3)
O5—N3—C10—C11	−179.0 (3)	S1—C7—C12—C11	−175.55 (18)
O6—N3—C10—C9	−177.6 (3)	C8—C7—C12—N4	−179.7 (2)
O6—N3—C10—C11	1.7 (4)	C8—C7—C12—C11	2.6 (3)
O7—N4—C12—C7	175.5 (2)	C7—C8—C9—C10	−0.5 (4)
O7—N4—C12—C11	−6.8 (3)	C8—C9—C10—N3	−178.9 (3)
O8—N4—C12—C7	−5.0 (3)	C8—C9—C10—C11	1.9 (4)
O8—N4—C12—C11	172.8 (2)	N3—C10—C11—C12	179.7 (2)
S1—C1—C2—N1	−8.8 (4)	C9—C10—C11—C12	−1.0 (4)
S1—C1—C2—C3	171.3 (2)	C10—C11—C12—N4	−179.1 (2)
C6—C1—C2—N1	−179.9 (3)	C10—C11—C12—C7	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O8i	0.93	2.54	3.080 (3)	117
C6—H6···O7ii	0.93	2.49	3.364 (3)	156
C11—H11···O2iii	0.93	2.57	3.489 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O8i	0.93	2.54	3.080 (3)	117
C6—H6⋯O7ii	0.93	2.49	3.364 (3)	156
C11—H11⋯O2iii	0.93	2.57	3.489 (3)	168

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