1,3-Dimethyl­benzo[b]dibenzothio­phene

P R Umarani; A Marx; V Dhayalan; A K Mohanakrishnan; V Manivannan

doi:10.1107/S1600536809003456

. 2009 Jan 31;65(Pt 2):o440. doi: 10.1107/S1600536809003456

1,3-Dimethylbenzo[b]dibenzothiophene

P R Umarani ^a, A Marx ^a, V Dhayalan ^b, A K Mohanakrishnan ^b, V Manivannan ^a,^*

PMCID: PMC2968210 PMID: 21582025

Abstract

The molecule of the title compound, C₁₈H₁₄S, is approximately planar (r.m.s. deviation = 0.029 Å). The crystal packing is stabilized by weak intermolecular C—H⋯π interactions.

Related literature

For the pharmacological activities of thiophen derivatives, see: Dzhurayev et al. (1992 ▶); El-Maghraby et al. (1984 ▶); Gewald et al. (1996 ▶). For related structures, see: Harrison et al. (2006 ▶); Palani et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₈H₁₄S
M _r = 262.35
Monoclinic,
a = 10.0219 (3) Å
b = 5.8692 (5) Å
c = 22.8554 (5) Å
β = 99.787 (1)°
V = 1324.80 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 (2) K
0.26 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.944, T _max = 0.961
27929 measured reflections
3030 independent reflections
2574 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.137
S = 1.08
3030 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.26 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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003456/bt2861sup1.cif

e-65-0o440-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003456/bt2861Isup2.hkl

e-65-0o440-Isup2.hkl^{(145.7KB, hkl)}

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

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

Cg1 is the centroid of the C7–C9/C14–C16 ring and Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17C⋯Cg1ⁱ	0.96	2.68	3.486 (2)	142
C18—H18A⋯Cg2ⁱⁱ	0.96	2.75	3.649 (3)	155

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

supplementary crystallographic information

Comment

Thiophen derivatives possess pharmacological activities such as anti-bacterial, anti-cancer, anti-inflammatory (El-Maghraby et al., 1984; Dzhurayev et al., 1992) and anti-toxic properties (Gewald et al., 1996).

The geometric parameters of the title molecule (Fig. 1) agree well with related structures (Harrison et al., 2006; Palani et al., 2006) and literature values (Allen et al., 1987). All non-H atoms lie in a common plane (r.m.s. deviation 0.029Å) .

The crystal packing is stabilized by weak intermolecular C - H···π [C17—H17C···Cg1 (1 - x, -y, 1 - z), H17C···Cg1 = 2.68 Å, C18—H18A··· Cg2 (1 + x, y, z), H18A···Cg1 = 2.75 Å; Cg1 and Cg2 are the centroid of rings defined by atoms C7/C8/C9/C14/C15/C16 and C1—C6, respectively) interactions. No significant intra- and intermolecular hydrogen bonds are observed.

Experimental

To a solution of diethyl 2-((2-(bromomethyl)banzo[b]thiophen-3-yl) methylene)malonate (0.35 g, 0.88 mmol) in dry 1,2-DCE (15 ml), ZnBr₂ (0.39 g, 1.73 mmol) and m-xylene (0.13 ml, 1.03 mmol), were added. The reaction mixture was then refluxed for 2 h under N₂ atmosphere. It was then poured over ice-water (50 ml) containing 2 ml of conc.HCl, extracted with chloroform (3 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 1,3-dimethylbenzo[2,3-b] dibenzothiophene as a colourless crystal.