Crystal structure of 2-(p-tol­yl)-6-(tri­fluoro­meth­yl)benzo[b]thio­phene-3-carbo­nitrile

N C Sandhya; S Naveen; N K Lokanath; S Ananda

doi:10.1107/S2056989015008671

. 2015 May 9;71(Pt 6):o382. doi: 10.1107/S2056989015008671

Crystal structure of 2-(p-tolyl)-6-(trifluoromethyl)benzo[b]thiophene-3-carbonitrile

N C Sandhya ^a, S Naveen ^b, N K Lokanath ^c, S Ananda ^a,^*

PMCID: PMC4459355 PMID: 26090178

Abstract

In the title compound, C₁₇H₁₀F₃NS, the dihedral angle between the fused benzothiophene ring system (r.m.s. deviation = 0.042 Å) and the benzene ring is 29.78 (11)°. The crystal structure features C—H⋯F and very weak C—H⋯N hydrogen bonds, which generate (001) sheets.

Keywords: crystal structure, benzo[b]thiophene, hydrogen bonding

Related literature

For background to benzothiophene derivatives, see: Bettinetti et al. (2002 ▸); Roberts & Hartley (2004 ▸). graphic file with name e-71-0o382-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₀F₃NS
M _r = 317.33
Monoclinic,
a = 13.7576 (5) Å
b = 14.5343 (6) Å
c = 7.1353 (3) Å
β = 92.817 (3)°
V = 1425.03 (10) Å³
Z = 4
Cu Kα radiation
μ = 2.29 mm⁻¹
T = 293 K
0.30 × 0.27 × 0.25 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T _min = 0.546, T _max = 0.598
7045 measured reflections
2316 independent reflections
1860 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.141
S = 1.06
2316 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); 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: PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015008671/hb7416sup1.cif

e-71-0o382-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008671/hb7416Isup2.hkl

e-71-0o382-Isup2.hkl^{(113.9KB, hkl)}

Click here for additional data file.^{(5.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015008671/hb7416Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015008671/hb7416fig1.tif

A view of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.^{(2.2MB, tif)}

a . DOI: 10.1107/S2056989015008671/hb7416fig2.tif

A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 2 for details).

CCDC reference: 1063141

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C3H3N11ⁱ	0.93	2.62	3.411(4)	143
C22H22CF15ⁱⁱ	0.96	2.45	3.375(4)	162

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

Acknowledgments

The authors are thankful to Institution of Excellence, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction facility.

supplementary crystallographic information

S1. Comment

Benzo[b]thiophene derivatives are important heterocyclic compounds because of their various applications in medicinal chemistry. They represent an important heterocyclic core and are shown to display a range of promising pharmacological properties such as antipsychotic, antidepressive, antithrombolytic, dopamine receptor antagonist and 5-lipoxygenase inhibitor. Number of 2-arylbenzo[b]thiophene derivatives have indeed, these sulfur heterocycles are essential components of clinically important drugs such as Clopidogrel (Bettinetti et al., 2002), Raloxifene (Roberts & Hartley, 2004) and Zileuton.

S2. Experimental

To a solution of 2-(2-chlorophenyl)acetonitrile (1.0 mmol), methyl benzodithioate (1.0 mmol) in DMF (2 ml), K₃PO₄ (2.0 mmol), pivalic acid (1.5 mmol), cuprous iodide (0.2 mmol) were added. The mixture was stirred at 80°C and progress was monitored by TLC. When the dithioesters could no longer be detected, the reaction mixture was extracted with EtOAc (3 × 10 ml). The organic layer was dried over anhydrous Na₂SO₄. The solvent was then removed under reduced pressure and the residue was purified by silica gel chromatography. White solid single crystals were obtained from slow evaporation of its solvent.