9H-Carbazole-9-carbo­thioic di­thio­peroxy­anhydride

Uludağ, N.; Ateş, M.; Çaylak Delibaş, N.; Çelik, Ö.; Hökelek, T.

doi:10.1107/S1600536813010349

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o771

https://doi.org/10.1107/S1600536813010349

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9H-Carbazole-9-carbothioic dithioperoxyanhydride

Nesimi Uludağ,^a Murat Ateş,^a Nagihan Çaylak Delibaş,^b Ömer Çelik ^c and Tuncer Hökelek ^d ^*

^aDepartment of Chemistry, Namık Kemal University, 59030 Değirmenaltı, Tekirdağ, Turkey, ^bDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, ^cDepartment of Physics, Dicle University, 21280 Sur, Diyarbakır, Turkey, and ^dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 10 April 2013; accepted 16 April 2013; online 20 April 2013)

The whole molecule 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 molecules, 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_r = 484.69
Orthorhombic, P 22₁ 2₁
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[F² > 2σ(F²)] = 0.072
wR(F²) = 0.156
S = 1.41
4100 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813010349/su2587sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813010349/su2587Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813010349/su2587Isup3.cml

checkCIF report

Comment top

Tetrahydrocarbazole systems are present in the framework of a number of indole-type alkaloids of biological interest (Saxton, 1983). The structures of tricyclic, tetracyclic and pentacyclic ring systems with dithiolane and other substituents of the tetrahydrocarbazole core, have been reported previously (Hökelek et al., 1994; Patır et al., 1997; Hökelek et al., 1998; Hökelek et al., 1999; Hökelek & Patır, 1999). Substituted carbazole based monomers exhibit good electroactive and photoactive properties which make them the most promising candidates for hole transporting mobility of charge carriers (Cloutet et al., 1999) and photoluminescence efficiencies (Zhenhong et al., 2006). Carbazole based heterocyclic polymer systems can be chemically or electrochemically polymerized to yield materials with interesting properties with a number of applications, such as electroluminescent (Tirapattur et al., 2003), photoactive devices (Taoudi et al., 2001), sensors and rechargable batteries (Saraswathi et al., 1999) and electrochromic displays (Sarac et al., 2000). The title compound, (I), may be considered as a synthetic precursor of tetracyclic indole alkaloids of biological interests. The present study was undertaken to ascertain its crystal structure.

The asymmetric unit of the title compound contains one half of the molecule, the whole molecule being generated by two-fold rotational symmetry (Fig. 1). It consists of a carbazole skeleton with a dithioperoxyanhydride group , where the bond lengths and angles are within normal ranges, and generally agree with those in the previously reported compounds (Hökelek et al., 1994; Patır et al., 1997; Hökelek et al., 1998; Hökelek et al., 1999; Hökelek & Patır, 1999) in all of which atom N9 is substituted.

An examination of the deviations from the mean planes through individual rings shows that rings A (C1-C4/C4a/C9a), B (C4a/C5a/C8a/N9/C9a) and C (C5a/C5-C8/C8a) are planar [symmetry code: (a) x, -y+1, -z]. The carbazole skeleton, containing rings A, B and C is also nearly coplanar [maximum deviation of -0.054 (5) Å for atom C8] with dihedral angles of A/B = 3.80 (15), A/C = 3.74 (17) and B/C = 3.21 (16) °. Atoms S1, S2 and C10 are displaced by 1.4738 (13), -0.5052 (15) and 0.2107 (42) Å from the mean plane of the carbazole skeleton.

In the crystal, molecules are stacked nearly parallel to (110) [Fig. 2]. The π–π contacts between the pyrrole and benzene rings, Cg1—Cg2ⁱ and Cg1···Cg3ⁱⁱ [symmetry codes: (i) x + 1, y, z; (ii) x - 1, y, z; where Cg1, Cg2 and Cg3 are centroids of the rings A (C1-C4/C4a/C9a), B (C4a/C5a/C8a/N9/C9a) and C (C5a/C5-C8/C8a), respectively] may stabilize the structure, with centroid-centroid distances of 3.948 (3) and 3.751 (3) Å, respectively.

Related literature top

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 top

Carbazole (0.80 g, 5 mmol) was added to a suspension of KOH (0.28 g, 20 mmol) in DMSO (20 ml) under vigorous stirring. The reaction mixture was stirred overnight at room temperature under O₂. Carbon disulfide (0.40 g, 5 mmol) was added drop wise, and then the mixture stirred for 10 h at room temperature. The resultant reaction mixture was poured into a large amount of deionized water. The solid obtained was filtered and purified by recrystallization from diethyl ether [yield: 1.30 g, 50%], yielding rod-shaped orange crystals.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom numbering [symmetry code: (a) x, -y+1, -z]. Displacement ellipsoids are drawn at the 50% probability level
	Fig. 2. A view along the c-axis of the crystal packing of the title compound (a-axis horizontal; b-axis vertical). Hydrogen atoms have been omitted for clarity.

9H-Carbazole-9-carbothioic dithioperoxyanhydride top

Crystal data top

C₂₆H₁₆N₂S₄	F(000) = 500
M_r = 484.69	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.P)² + 0.892P] where P = (F_o² + 2F_c²)/3
S = 1.41	(Δ/σ)_max < 0.001
4100 reflections	Δρ_max = 0.35 e Å⁻³
145 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1548 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (18)

Crystal data top

C₂₆H₁₆N₂S₄	V = 1062.79 (7) Å³
M_r = 484.69	Z = 2
Orthorhombic, P22₁2₁	Mo Kα radiation
a = 3.9207 (2) Å	µ = 0.47 mm⁻¹
b = 14.9355 (4) Å	T = 294 K
c = 18.1494 (5) Å	0.35 × 0.15 × 0.10 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4100 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2471 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.954	R_int = 0.036
5384 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	H-atom parameters constrained
wR(F²) = 0.156	Δρ_max = 0.35 e Å⁻³
S = 1.41	Δρ_min = −0.47 e Å⁻³
4100 reflections	Absolute structure: Flack (1983), 1548 Friedel pairs
145 parameters	Absolute structure parameter: 0.04 (18)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₆N₂S₄
M_r	484.69
Crystal system, space group	Orthorhombic, P22₁2₁
Temperature (K)	294
a, b, c (Å)	3.9207 (2), 14.9355 (4), 18.1494 (5)
V (Å³)	1062.79 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.35 × 0.15 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.920, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	5384, 4100, 2471
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.808

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.156, 1.41
No. of reflections	4100
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.47
Absolute structure	Flack (1983), 1548 Friedel pairs
Absolute structure parameter	0.04 (18)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Acknowledgements

The authors are indebted to Dicle University Scientific and Technological Applied and Research Center, Diyarbakır, Turkey, for use of the X-ray diffractometer.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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