1-(Phenyl­sulfon­yl)benzo[1,2:2′,3′]thieno[5′,4′-b]carbazole

S Thenmozhi; A SubbiahPandi; V Dhayalan; A K MohanaKrishnan

doi:10.1107/S1600536810010044

. 2010 Mar 27;66(Pt 4):o954. doi: 10.1107/S1600536810010044

1-(Phenylsulfonyl)benzo[1,2:2′,3′]thieno[5′,4′-b]carbazole

S Thenmozhi ^a, A SubbiahPandi ^a,^*, V Dhayalan ^b, A K MohanaKrishnan ^b

PMCID: PMC2983998 PMID: 21580758

Abstract

In the title compound, C₂₄H₁₅NO₂S₂, the ring system composed of the five fused rings is almost planar (r.m.s. deviation for all non-H atoms = 0.056 Å). The dihedral angle between the fused ring system and the phenyl ring is 83.4 (9)°. The crystal packing is stabilized by C—H⋯π and π–π interactions between parallel ring systems [centroid–centroid distances = 3.526 (3), 3.877 (3) and 3.712 (3) Å].

Related literature

For related structures, see: Murugavel et al. (2009 ▶); Chakkaravarthi et al. (2008 ▶); Ravishankar et al. (2005 ▶).

Experimental

Crystal data

C₂₄H₁₅NO₂S₂
M _r = 413.49
Triclinic,
a = 7.463 (5) Å
b = 10.462 (5) Å
c = 12.335 (5) Å
α = 80.438 (5)°
β = 89.433 (5)°
γ = 81.876 (5)°
V = 940.1 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.981, T _max = 0.985
24843 measured reflections
6428 independent reflections
4863 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.192
S = 1.01
6428 reflections
262 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.62 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 global, I. DOI: 10.1107/S1600536810010044/bt5204sup1.cif

e-66-0o954-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010044/bt5204Isup2.hkl

e-66-0o954-Isup2.hkl^{(308.2KB, hkl)}

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

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

Cg6 is the centeroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Cg6ⁱ	0.93	2.78	3.685 (4)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

ST and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Carbazole and its derivatives have become quite attractive compounds owing to their applications in pharmacy and molecular electronics.

In order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

The ring system composed of the five rings is almost planar (r.m.s. deviation for all non-H atoms 0.056Å). The crystal packing is stabilized by C–H..O and C–H···π (Table. 1) hydrogen bonds. In addition, there are π–π interactions between the extended ring system with a mean distance between the ring planes of 3.7Å.

Experimental

To a solution of diethyl-2-((2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl) methylene)malonate (0.3 g 0.57 mmol) in dry 1,2-DCE (10 ml), InBr3 (0.02 g 0.06 mmol) and benzo[b]thiophene (0.09 g, 0.67 mmol) were added. The reaction mixture was stirred at room temperature for 4 h and then refluxed for 1 h under N2 atmosphere. It was then poured over ice-water (30 ml) containing 1 ml of Conc.HCl, extracted with chloroform (2 X 10 ml) and dried (Na₂SO₄). The removal of solvent followed by flash column chromatographic purification (silica gel, 230-420 mesh, n-hexane/ethyl acetate 99:1) afforded the product as a colorless solid. The product was recrystallization from CDCl₃