8,9-Dimeth­oxy-5-phenyl­sulfonyl-5H-benzo[b]carbazole

T Kavitha; M Thenmozhi; V Dhayalan; A K Mohanakrishnan; M N Ponnuswamy

doi:10.1107/S160053681001247X

. 2010 Apr 14;66(Pt 5):o1071. doi: 10.1107/S160053681001247X

8,9-Dimethoxy-5-phenylsulfonyl-5H-benzo[b]carbazole

T Kavitha ^a, M Thenmozhi ^a, V Dhayalan ^b, A K Mohanakrishnan ^b, M N Ponnuswamy ^a,^*

PMCID: PMC2979030 PMID: 21579126

Abstract

In the title compound, C₂₄H₁₉NO₄S, the benzocarbazole ring system is planar (r.m.s. deviation = 0.016 Å) and forms a dihedral angle of 78.54 (4)° with the sulfonyl-bound phenyl ring. Intramolecular C—H⋯O interactions are observed. A C(8) chain running along the b axis is formed via intermolecular C—H⋯O hydrogen bonds. The chains are linked via weak C—H⋯ π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For the biological activity of carbazole derivatives, see: Itoigawa et al. (2000 ▶); Tachibana et al. (2001 ▶); Ramsewak et al. (1999 ▶). For related structures, see: Chakkaravarthi et al. (2008 ▶); Govindasamy et al. (1998 ▶).

Experimental

Crystal data

C₂₄H₁₉NO₄S
M _r = 417.46
Triclinic,
a = 7.8606 (2) Å
b = 9.5892 (2) Å
c = 13.8846 (4) Å
α = 100.387 (1)°
β = 93.168 (2)°
γ = 105.883 (1)°
V = 984.05 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.943, T _max = 0.962
26246 measured reflections
7025 independent reflections
5372 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.138
S = 1.04
7025 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001247X/ci5059sup1.cif

e-66-o1071-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001247X/ci5059Isup2.hkl

e-66-o1071-Isup2.hkl^{(336.8KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1	0.93	2.34	2.9238 (19)	120
C6—H6⋯O2	0.93	2.37	2.9674 (15)	122
C2—H2⋯O2ⁱ	0.93	2.55	3.3361 (17)	143
C24—H24C⋯Cg1ⁱⁱ	0.96	2.84	3.727 (2)	154
C25—H25A⋯Cg2ⁱⁱⁱ	0.96	2.90	3.628 (2)	134

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C7–C10/C22/C23 and C1–C4/C21/C20 rings, respectively.

Acknowledgments

TK thanks the CSIR, India, for financial support in the form of a senior research fellowship.

supplementary crystallographic information

Comment

Carbazole and its derivatives are considered as potential compounds owing to their applications in pharmacy and molecular electronics. They also possess various biological activities such as antitumor (Itoigawa et al., 2000), antioxidative (Tachibana et al., 2001), anti-inflammatory and antimutagenic (Ramsewak et al., 1999) properties.

The benzocarbazole ring system is planar (r.m.s. deviation 0.016 Å) and it forms a dihedral angle of 78.54 (4)° with the sulfonyl-bound phenyl ring (Fig.1). The N—C bond lengths, namely N5—C19 and N5—C21 [1.432 (1) & 1.436 (2) Å] deviate slightly from the mean value reported in the literature (1.370 (12) Å; Allen et al., 1987). This may be due to the electron-withdrawing character of the phenylsulfonyl group (Govindasamy et al., 1998) substitued at N atom of the carbazole group. The S atom exhibits a distorted tetrahedral geometry. The widening of the O1—S1—O2 [119.60 (6)°] angle may be due to repulsive interactions between the two S═O bonds (Chakkaravarthi et al., 2008). The sum of the bond angles around N1 [350.6°] indicate the sp² hybridization. The methoxy groups substituted at C8 and C9 lie almost in the plane of the attached benzene ring [C7—C8—O3—C24 = -3.8 (2)° and C10—C9—O4—C25 = 6.8 (2)°].

The intermolecular C—H···O hydrogen bonds link the molecules into a C(8) chain running along the b axis (Fig.2). The packing of the molecules is further influenced by C—H··· π interactions.

Experimental

To a solution of diethyl-2-[(2-bromomethyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate (0.41 g, 0.78 mmol) in dry 1,2-dichloroethane (15 ml), anhydrous ZnBr₂ (0.35 g, 1.55 mmol) and veratrole (0.12 ml, 0.94 mmol) were added. The mixture was refluxed for 5 h under N₂ atmosphere. The solvent was removed and the reaction mixture was quenched with ice-water (50 ml) containing 1 ml of conc. HCl, extracted with chloroform (2 × 10 ml) and dried (Na₂SO₄). Removal of the solvent followed by flash column chromatographic purification (n-hexane-ethyl acetate 99:1) led to the isolation of the title compound as a colourless solid. The compound was recrystallized from CDCl₃.