9H-Carbazole-9-carbo-thioic di-thio-peroxy-anhydride.

The whole mol-ecule of the title compound, C26H16N2S4, is generated by twofold rotational symmetry. The carbazole skeleton is nearly planar [maximum deviation = 0.054 (5) Å]. In the crystal, aromatic π-π stacking is observed between parallel carbazole ring systems of adjacent mol-ecules, the shortest centroid-centroid distances between pyrrole and benzene rings being 3.948 (3) and 3.751 (3) Å.

Related literature

For tetra­hydro­carbazole systems present in the framework of a number of indole-type alkaloids of biological inter­est, see: Saxton (1983 ▶). For related structures, see: Hökelek et al. (1994 ▶, 1998 ▶, 1999 ▶); Patır et al. (1997 ▶); Hökelek & Patır (1999 ▶). For hole-transporting mobility of charge carriers, see: Cloutet et al. (1999 ▶). For photoluminescence efficiencies, see: Zhenhong et al. (2006 ▶). For electroluminescent applications, see: Tirapattur et al. (2003 ▶). For photoactive devices, see: Taoudi et al. (2001 ▶). For sensors and rechargable batteries, see: Saraswathi et al. (1999 ▶). For electrochromic displays, see: Sarac et al. (2000 ▶).

Experimental

Crystal data

C26H16N2S4

M = 484.69

Orthorhombic,

a = 3.9207 (2) Å

b = 14.9355 (4) Å

c = 18.1494 (5) Å

V = 1062.79 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.47 mm−1

T = 294 K

0.35 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.920, T max = 0.954

5384 measured reflections

4100 independent reflections

2471 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.156

S = 1.41

4100 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 1548 Friedel pairs

Flack parameter: 0.04 (18)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010349/su2587sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010349/su2587Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010349/su2587Isup3.cml

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

C26H16N2S4	F(000) = 500
Mr = 484.69	Dx = 1.514 Mg m−3
Orthorhombic, P22121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2bc 2	Cell parameters from 2694 reflections
a = 3.9207 (2) Å	θ = 6.2–28.7°
b = 14.9355 (4) Å	µ = 0.47 mm−1
c = 18.1494 (5) Å	T = 294 K
V = 1062.79 (7) Å3	Rod, orange
Z = 2	0.35 × 0.15 × 0.10 mm

Bruker Kappa APEXII CCD area-detector diffractometer	4100 independent reflections
Radiation source: fine-focus sealed tube	2471 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 35.1°, θmin = 6.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.920, Tmax = 0.954	k = −23→10
5384 measured reflections	l = −27→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.072	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.P)2 + 0.892P] where P = (Fo2 + 2Fc2)/3
S = 1.41	(Δ/σ)max < 0.001
4100 reflections	Δρmax = 0.35 e Å−3
145 parameters	Δρmin = −0.47 e Å−3
0 restraints	Absolute structure: Flack (1983), 1548 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (18)

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
S1	0.3301 (3)	0.43540 (7)	0.01656 (7)	0.0393 (3)
S2	0.0207 (4)	0.53764 (7)	0.14312 (8)	0.0452 (3)
C1	−0.0287 (13)	0.2527 (3)	0.0425 (3)	0.0379 (10)
H1	−0.0916	0.2958	0.0082	0.046*
C2	−0.0674 (12)	0.1620 (3)	0.0281 (3)	0.0446 (12)
H2	−0.1545	0.1440	−0.0172	0.054*
C3	0.0206 (17)	0.0976 (3)	0.0796 (3)	0.0511 (13)
H3	−0.0077	0.0374	0.0683	0.061*
C4	0.1490 (13)	0.1216 (3)	0.1470 (3)	0.0466 (12)
H4	0.2048	0.0781	0.1817	0.056*
C4A	0.1946 (11)	0.2119 (3)	0.1629 (2)	0.0335 (10)
C5	0.4408 (13)	0.2274 (3)	0.2947 (3)	0.0437 (12)
H5	0.4660	0.1664	0.3034	0.052*
C5A	0.3077 (12)	0.2574 (3)	0.2285 (2)	0.0337 (10)
C6	0.5352 (14)	0.2884 (3)	0.3473 (3)	0.0489 (13)
H6	0.6241	0.2686	0.3920	0.059*
C7	0.4988 (16)	0.3796 (3)	0.3344 (3)	0.0493 (13)
H7	0.5621	0.4200	0.3709	0.059*
C8	0.3715 (13)	0.4114 (3)	0.2690 (3)	0.0436 (12)
H8	0.3502	0.4726	0.2606	0.052*
C8A	0.2759 (11)	0.3501 (3)	0.2160 (2)	0.0313 (9)
N9	0.1597 (9)	0.3628 (2)	0.1418 (2)	0.0331 (8)
C9A	0.1079 (10)	0.2763 (3)	0.1103 (3)	0.0306 (10)
C10	0.1482 (11)	0.4442 (3)	0.1066 (2)	0.0316 (9)

	U11	U22	U33	U12	U13	U23
S1	0.0498 (6)	0.0332 (5)	0.0351 (6)	0.0087 (5)	0.0081 (6)	0.0058 (5)
S2	0.0588 (7)	0.0339 (5)	0.0428 (7)	0.0065 (6)	0.0051 (7)	−0.0033 (5)
C1	0.042 (2)	0.035 (2)	0.037 (3)	0.001 (2)	−0.004 (2)	0.0022 (19)
C2	0.050 (3)	0.042 (2)	0.042 (3)	−0.002 (2)	−0.008 (2)	−0.007 (2)
C3	0.070 (4)	0.031 (2)	0.052 (3)	−0.001 (3)	−0.003 (3)	−0.002 (2)
C4	0.060 (3)	0.032 (2)	0.048 (3)	0.003 (2)	−0.004 (3)	0.009 (2)
C4A	0.033 (2)	0.036 (2)	0.032 (3)	0.0024 (18)	0.003 (2)	0.0052 (18)
C5	0.045 (3)	0.047 (3)	0.038 (3)	0.002 (2)	−0.001 (2)	0.010 (2)
C5A	0.032 (2)	0.039 (2)	0.029 (3)	0.0000 (19)	0.003 (2)	0.0060 (19)
C6	0.048 (3)	0.067 (3)	0.031 (3)	−0.004 (3)	−0.008 (3)	0.012 (3)
C7	0.054 (3)	0.060 (3)	0.034 (3)	−0.013 (3)	−0.003 (3)	0.000 (2)
C8	0.053 (3)	0.043 (2)	0.035 (3)	−0.010 (2)	−0.003 (2)	−0.001 (2)
C8A	0.029 (2)	0.038 (2)	0.027 (2)	−0.0021 (17)	0.0025 (18)	0.0039 (18)
N9	0.0412 (19)	0.0308 (16)	0.0272 (19)	−0.0019 (15)	−0.002 (2)	0.0029 (16)
C9A	0.032 (2)	0.0288 (19)	0.031 (2)	−0.0005 (15)	0.0008 (18)	0.0013 (18)
C10	0.031 (2)	0.033 (2)	0.031 (2)	−0.0012 (17)	0.0003 (19)	0.0034 (18)

S1—S1i	2.021 (2)	C5—H5	0.9300
S1—C10	1.787 (4)	C5A—C4A	1.441 (6)
S2—C10	1.624 (4)	C5A—C5	1.384 (6)
C1—C9A	1.387 (6)	C5A—C8A	1.409 (6)
C1—H1	0.9300	C6—H6	0.9300
C2—C1	1.388 (6)	C7—C6	1.390 (7)
C2—C3	1.384 (7)	C7—C8	1.373 (7)
C2—H2	0.9300	C7—H7	0.9300
C3—H3	0.9300	C8—H8	0.9300
C4—C3	1.371 (7)	C8A—C8	1.380 (6)
C4—H4	0.9300	N9—C8A	1.433 (6)
C4A—C4	1.391 (6)	N9—C9A	1.428 (5)
C4A—C9A	1.397 (6)	N9—C10	1.375 (5)
C5—C6	1.370 (7)
C10—S1—S1i	101.63 (15)	C5—C6—C7	120.4 (5)
C2—C1—H1	121.4	C5—C6—H6	119.8
C9A—C1—C2	117.2 (4)	C7—C6—H6	119.8
C9A—C1—H1	121.4	C6—C7—H7	119.2
C1—C2—H2	119.2	C8—C7—C6	121.5 (5)
C3—C2—C1	121.6 (5)	C8—C7—H7	119.2
C3—C2—H2	119.2	C7—C8—C8A	118.2 (5)
C2—C3—H3	119.6	C7—C8—H8	120.9
C4—C3—C2	120.9 (4)	C8A—C8—H8	120.9
C4—C3—H3	119.6	C5A—C8A—N9	108.1 (4)
C3—C4—C4A	119.0 (4)	C8—C8A—N9	130.8 (4)
C3—C4—H4	120.5	C8—C8A—C5A	121.0 (4)
C4A—C4—H4	120.5	C9A—N9—C8A	107.5 (3)
C4—C4A—C5A	131.9 (4)	C10—N9—C8A	124.4 (3)
C4—C4A—C9A	119.7 (4)	C10—N9—C9A	127.5 (4)
C9A—C4A—C5A	108.3 (4)	C1—C9A—N9	129.8 (4)
C5A—C5—H5	120.3	C1—C9A—C4A	121.7 (4)
C6—C5—C5A	119.5 (4)	C4A—C9A—N9	108.4 (4)
C6—C5—H5	120.3	S2—C10—S1	124.0 (2)
C5—C5A—C4A	132.9 (4)	N9—C10—S1	110.3 (3)
C5—C5A—C8A	119.4 (4)	N9—C10—S2	125.4 (3)
C8A—C5A—C4A	107.6 (4)
S1i—S1—C10—S2	1.3 (3)	C4A—C5A—C8A—N9	−2.8 (5)
S1i—S1—C10—N9	−173.6 (3)	C4A—C5A—C8A—C8	−178.8 (4)
C2—C1—C9A—C4A	−1.7 (7)	C5—C5A—C8A—N9	175.2 (4)
C2—C1—C9A—N9	−176.2 (5)	C5—C5A—C8A—C8	−0.8 (7)
C3—C2—C1—C9A	1.1 (7)	C8—C7—C6—C5	−0.6 (9)
C1—C2—C3—C4	0.2 (9)	C6—C7—C8—C8A	0.7 (8)
C4A—C4—C3—C2	−0.9 (9)	N9—C8A—C8—C7	−175.0 (5)
C5A—C4A—C4—C3	176.9 (5)	C5A—C8A—C8—C7	0.0 (7)
C9A—C4A—C4—C3	0.3 (7)	C9A—N9—C8A—C5A	2.3 (5)
C4—C4A—C9A—C1	1.1 (7)	C9A—N9—C8A—C8	177.8 (5)
C4—C4A—C9A—N9	176.6 (4)	C10—N9—C8A—C5A	−169.8 (4)
C5A—C4A—C9A—C1	−176.3 (4)	C10—N9—C8A—C8	5.7 (7)
C5A—C4A—C9A—N9	−0.8 (5)	C8A—N9—C9A—C1	174.1 (4)
C5A—C5—C6—C7	−0.2 (8)	C8A—N9—C9A—C4A	−0.9 (5)
C5—C5A—C4A—C4	7.6 (10)	C10—N9—C9A—C1	−14.1 (7)
C5—C5A—C4A—C9A	−175.4 (5)	C10—N9—C9A—C4A	170.9 (4)
C8A—C5A—C4A—C4	−174.7 (5)	C8A—N9—C10—S1	132.7 (4)
C8A—C5A—C4A—C9A	2.2 (5)	C8A—N9—C10—S2	−42.1 (6)
C4A—C5A—C5—C6	178.3 (5)	C9A—N9—C10—S1	−37.7 (5)
C8A—C5A—C5—C6	0.9 (7)	C9A—N9—C10—S2	147.4 (4)