1-Naphthyl 9H-carbazole-4-sulfonate

R Arulmozhi; Jasmine P Vennila; Sunil Manohar Babu; Helen P Kavitha; V Manivannan

doi:10.1107/S1600536808016334

. 2008 Jun 7;64(Pt 7):o1208. doi: 10.1107/S1600536808016334

1-Naphthyl 9H-carbazole-4-sulfonate

R Arulmozhi ^a, Jasmine P Vennila ^b, Sunil Manohar Babu ^c, Helen P Kavitha ^d, V Manivannan ^e,^*

PMCID: PMC2961653 PMID: 21202847

Abstract

In the title compound, C₂₂H₁₅NO₃S, the plane of the carbazole ring system forms a dihedral angle of 65.06 (4)° with the naphthalene ring system. In the crystal structure, a weak intramolecular C—H⋯O interaction is observed between the naphthalene ring system and the sulfonate group. Two weak intermolecular C—H⋯O interactions are also observed.

Related literature

For biological activity, see: Itoigawa et al. (2000 ▶); Tachibana et al. (2001 ▶). For the structure of closely related compounds, see: Manivannan et al. (2005 ▶); Hosomi et al. (2000 ▶).

Experimental

Crystal data

C₂₂H₁₅NO₃S
M _r = 373.41
Orthorhombic,
a = 14.2365 (5) Å
b = 9.2098 (4) Å
c = 26.3865 (10) Å
V = 3459.7 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 (2) K
0.20 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.959, T _max = 0.971
22287 measured reflections
4600 independent reflections
2928 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.144
S = 1.05
4600 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2; cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016334/is2296sup1.cif

e-64-o1208-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016334/is2296Isup2.hkl

e-64-o1208-Isup2.hkl^{(220.9KB, 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
C2—H2⋯O2	0.93	2.42	2.835 (3)	107
C8—H8⋯O3ⁱ	0.93	2.50	3.403 (3)	164
C17—H17⋯O3ⁱⁱ	0.93	2.54	3.364 (3)	147

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Chennai, for the data collection.

supplementary crystallographic information

Comment

Carbazole derivatives possess various biological activities, such as antitumor (Itoigawa et al., 2000), antioxidative (Tachibana et al., 2001). We report the crystal structure of the title compound, (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported structures (Manivannan et al., 2005; Hosomi et al., 2000).

The plane of the carbazole ring forms a dihedral angle of 65.06 (4)° with the naphthalene ring. The torsion angles C2—C1—S1—O2 and C10—C1—S1—O3 [4.21 (19) ° and 46.22 (18)°, respectively] indicate a syn conformation of sulfonyl moiety. The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing is stabilized by weak intermolecular C—H···O interactions.

Experimental

1-Naphthalene sulfonyl chloride (1.19 g, 5.2 mmol) dissolved in methelene dichloride was slowly added to 9H carbazol-4-ol (0.9 g, 4.8 mmol), followed by the addition of triethylamine (0.72 g, 7 mmol) at 20 °C. The reaction mixture was warmed at 40 °C and maintained at that temperature for 4 h. The reaction mixture was cooled to 15 °C. and mixed with 10 ml of methelene dichloride and 10 ml of water. The methelene dichloride layer was separated, washed to neutral pH with 5% aqueous sodium dicarbonate solution, dried over anhydrous sodium sulfate and concentrated. The crude compound was recrystallized from toluene.