5-Methyl-12-phenyl­sulfonyl-12H-naphtho­[1,2-b]carbazole

S Vasudhevan; R Joel Karunakaran

doi:10.1107/S160053681104949X

. 2011 Nov 30;67(Pt 12):o3480. doi: 10.1107/S160053681104949X

5-Methyl-12-phenylsulfonyl-12H-naphtho[1,2-b]carbazole

S Vasudhevan ^a, R Joel Karunakaran ^a,^*

PMCID: PMC3239104 PMID: 22199952

Abstract

In the title compound, C₂₇H₁₉NO₂S, the naphthocarbazole unit is approximately planar (r.m.s. deviation = 0.002 Å) except for the N atom, which is displaced by 0.122 (1) Å out of the mean plane. The dihedral angle between the naphthocarbazole mean plane and the phenyl ring of the phenylsulfonyl substituent is 83.16 (3)°. An intermolecular C—H⋯π interaction involving the phenyl group and the pyrrole ring is observed in the crystal structure.

Related literature

For the biological activity of indole and carbazole derivatives see: Chai et al. (2006 ▶); Rani et al. (2004 ▶); Panwar et al. (2006 ▶); Abele et al. (2003 ▶). For related structures see: Chakkaravarthi et al. (2007 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

C₂₇H₁₉NO₂S
M _r = 421.49
Triclinic,
a = 9.4527 (3) Å
b = 10.7457 (3) Å
c = 11.5791 (3) Å
α = 115.592 (1)°
β = 93.324 (2)°
γ = 105.206 (2)°
V = 1003.61 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.946, T _max = 0.964
23737 measured reflections
5360 independent reflections
4477 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.120
S = 1.05
5360 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.29 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104949X/bh2396sup1.cif

e-67-o3480-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104949X/bh2396Isup2.hkl

e-67-o3480-Isup2.hkl^{(257.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681104949X/bh2396Isup3.cml

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

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

Cg1 is the centroid of the pyrrole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯Cg1ⁱ	0.93	2.61	3.4770 (2)	156

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Dr Babu Varghese, SAIF, IIT, Madras, Chennai, for the X-ray data collection.

supplementary crystallographic information

Comment

Heterocyclic compounds containing pyrrole ring with benzene ring fused to α,β-position with π electrons and lone pair from the nitrogen atom are biologically accepted pharmacophore in medicinal compounds and possesses a wide spectrum of biological activities (Chai et al., 2006). Biological activity includes anticancer, anti-inflammatory (Rani et al., 2004), analgesic, antimicrobial (Panwar et al., 2006) and antifungal (Abele et al., 2003) properties.

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Chakkaravarthi et al., 2007; Liu et al., 2007). The naphtho-carbazole moiety is planar except that the nitrogen atom N1 is 0.122 Å out of the mean plane. Dihedral angle between the mean plane of the naphtho-carbazole moiety and the phenyl group is 83.16 (3)°. The geometry of bonding of sulfur atom is tetrahedral except that angle O1—S1—O2 is 120.40 (6)°. There is a C—H···π interaction between the five membered ring (C1, C6, C7, C8 and N1) and H25ⁱ (symmetry code: i = -x, -y, 1 - z) of the phenyl ring. The separation between the H atom and the centroid of the five membered ring is 2.61 Å.

Experimental

To a solution of diethyl-2-((bromomethyl-1-(phenylsulfonyl)-1H- indole-3-yl)methylene)malonate (0.2 g, 0.38 mmol) in dry 1,2-DCE (10 ml), ZnBr₂ (0.17 g, 0.75 mmol) and 1-methylnaphthalene (0.06 ml, 0.42 mmol) were added. The reaction mixture was then refluxed for 1 h under nitrogen atmosphere. It was then poured over ice-water (50 ml) containing 2 ml of conc. HCl, extracted with chloroform (3 × 10 ml) and dried over Na₂SO₄. The removal of solvent followed by flash column chromatographic purification (silica gel, 230–420 mesh, n-hexane/ethyl acetate 96:4) afforded the title carbazole as a colourless solid. Recrystallization was done using CDCl₃ as solvent.