5-Methyl­phenanthro[2,3-b]thio­phene

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

doi:10.1107/S1600536811014838

. 2011 Apr 29;67(Pt 5):o1243. doi: 10.1107/S1600536811014838

5-Methylphenanthro[2,3-b]thiophene

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

PMCID: PMC3089194 PMID: 21754536

Abstract

The title compound, C₁₇H₁₂S, which crystallises with two molecules in the asymmetric unit, features four fused rings forming an essentially planar molecule, with maximum deviations from the mean plane of 0.078 (2) and 0.080 (2) Å for C atoms of the thiophene and phenanthrene groups in both the molecules. The crystal packing features weak C—H⋯π interactions.

Related literature

For a related structure, see: Gunasekaran et al. (2010 ▶).

Experimental

Crystal data

C₁₇H₁₂S
M _r = 248.33
Monoclinic,
a = 18.7011 (10) Å
b = 5.8199 (3) Å
c = 23.4546 (14) Å
β = 105.158 (2)°
V = 2463.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.24 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
31917 measured reflections
6983 independent reflections
4446 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.195
S = 1.06
6983 reflections
327 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); 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/S1600536811014838/bt5506sup1.cif

e-67-o1243-sup1.cif^{(25KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014838/bt5506Isup2.hkl

e-67-o1243-Isup2.hkl^{(334.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811014838/bt5506Isup3.cml

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⋯Cg4ⁱ	0.93	2.84	3.612 (3)	141
C2′—H2′⋯Cg14ⁱⁱ	0.93	2.85	3.619 (3)	141
C11—H11⋯Cg1ⁱ	0.93	2.72	3.515 (3)	144
C11′—H11′⋯Cg11ⁱⁱ	0.93	2.82	3.610 (3)	143
C17′—H17B⋯Cg14ⁱⁱⁱ	0.96	2.98	3.581 (3)	121
C17—H17F⋯Cg4ⁱⁱⁱ	0.96	2.92	3.565 (3)	125

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1, Cg4, Cg11 and Cg14 are the centroids of the S1/C1–C4, C9–C14, S1′/C1′–C4′ and C9′–C14′ rings, respectively.

Acknowledgments

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

supplementary crystallographic information

Comment

X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles in (Fig. 1) agree with those observed in other benzothiophene derivative (Gunasekaran et al., 2010). Both molecules are essentially planar, with maximum deviation of 0.078 (2) and 0.080 (2)Å for atoms C2 and C10'. The molecules lack hydrogen bonding functionality and pack in layers parallel to the (010) planes.In addition to van der Waals interaction, the crystal packing is stabilized by C–H···π hydrogen bonds (Table. 1).

Experimental

To a solution of diethyl-2-((3-(bromomethyl)thiophen-2-yl)methylene) malonate (1 g, 2.88 mmol) in dry 1,2-dichloroethane (10ml), 1-methylnaphthalene (0.49 g, 3.44 mmol) and anhydrous ZnBr₂ (0.64 g, 2.84 mmol) were added. sIt was then stirred at room temperature for 8 h and then refluxed for 1 h under N₂ atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml) containing 1 ml of conc. HCl, extracted with chloroform (3 x 10 ml) and dried (Na₂SO₄). Removal of the solvent followed by flash column chromatography purification (n-hexane/ethyl acetate 99:1) led to the isolation of 5-methyl phenanthro[2,3-b]thiophene as a colorless crystals. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.