5-Methyl­phenanthro[2,3-b]thio­phene

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

doi:10.1107/S1600536811014838

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1243

doi:10.1107/S1600536811014838

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5-Methylphenanthro[2,3-b]thiophene

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

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 30 March 2011; accepted 20 April 2011; online 29 April 2011)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.055
wR(F²) = 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

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
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z. Cg1, Cg4, Cg11 and Cg14 are the centroids of the S1/C1–C4, C9–C14, S1′/C1′–C4′ and C9′–C14′ rings, respectively.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014838/bt5506sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811014838/bt5506Isup3.cml

checkCIF report

Comment top

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).

Related literature top

For related structures, see: Gunasekaran et al. (2010).

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of showing the atom-numbering scheme and intramolecular hydrogen bond. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. C—H···π interactions (dotted lines) in the title compound. Cg denotes ring centeroid. [Symmetry code:(i) 3/2-X,1/2+Y,1/2-Z; (ii) X,-1+Y,Z; (iii) X,-1+Y,Z; (iv) 1/2-X,1/2+Y,1/2-Z]

5-Methylphenanthro[2,3-b]thiophene top

Crystal data top

C₁₇H₁₂S	F(000) = 1040
M_r = 248.33	D_x = 1.339 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6983 reflections
a = 18.7011 (10) Å	θ = 1.3–29.7°
b = 5.8199 (3) Å	µ = 0.24 mm⁻¹
c = 23.4546 (14) Å	T = 293 K
β = 105.158 (2)°	Block, colourless
V = 2463.9 (2) Å³	0.25 × 0.22 × 0.19 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	6983 independent reflections
Radiation source: fine-focus sealed tube	4446 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and ϕ scans	θ_max = 29.7°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→26
T_min = 0.981, T_max = 0.985	k = −8→8
31917 measured reflections	l = −32→32

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1022P)² + 0.5162P] where P = (F_o² + 2F_c²)/3
6983 reflections	(Δ/σ)_max = 0.001
327 parameters	Δρ_max = 0.47 e Å⁻³
2 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₇H₁₂S	V = 2463.9 (2) Å³
M_r = 248.33	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 18.7011 (10) Å	µ = 0.24 mm⁻¹
b = 5.8199 (3) Å	T = 293 K
c = 23.4546 (14) Å	0.25 × 0.22 × 0.19 mm
β = 105.158 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	6983 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4446 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.032
31917 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	2 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.06	Δρ_max = 0.47 e Å⁻³
6983 reflections	Δρ_min = −0.30 e Å⁻³
327 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1'	0.33522 (15)	0.2874 (5)	0.07093 (11)	0.0702 (7)
H1'	0.3227	0.3551	0.0337	0.084*
C1	0.55737 (13)	0.7887 (4)	0.06335 (10)	0.0601 (6)
H1	0.5490	0.8546	0.0261	0.072*
C2	0.60214 (13)	0.8818 (4)	0.11144 (10)	0.0516 (5)
H2	0.6274	1.0193	0.1114	0.062*
C2'	0.31625 (12)	0.3776 (4)	0.11600 (10)	0.0538 (5)
H2'	0.2897	0.5136	0.1144	0.065*
C3	0.60700 (11)	0.7451 (3)	0.16387 (9)	0.0431 (4)
C3'	0.34245 (11)	0.2359 (3)	0.16957 (9)	0.0449 (4)
C4	0.56138 (11)	0.5470 (3)	0.15084 (9)	0.0457 (4)
C4'	0.38181 (11)	0.0412 (3)	0.15862 (9)	0.0451 (4)
C5	0.55612 (11)	0.3950 (3)	0.19459 (10)	0.0487 (5)
H5	0.5255	0.2669	0.1856	0.058*
C5'	0.41350 (11)	−0.1131 (4)	0.20223 (10)	0.0496 (5)
H5'	0.4394	−0.2397	0.1939	0.059*
C6'	0.40615 (10)	−0.0763 (3)	0.25924 (9)	0.0438 (4)
C6	0.59727 (11)	0.4349 (3)	0.25262 (9)	0.0446 (4)
C7	0.64532 (10)	0.6288 (3)	0.26671 (9)	0.0411 (4)
C7'	0.36605 (10)	0.1153 (3)	0.27204 (8)	0.0406 (4)
C8'	0.33449 (11)	0.2692 (3)	0.22664 (9)	0.0461 (4)
H8'	0.3079	0.3951	0.2345	0.055*
C8	0.64871 (11)	0.7820 (3)	0.22128 (9)	0.0437 (4)
H8	0.6794	0.9101	0.2298	0.052*
C9'	0.35973 (10)	0.1459 (3)	0.33238 (9)	0.0431 (4)
C9	0.68848 (11)	0.6597 (3)	0.32765 (8)	0.0416 (4)
C10'	0.31838 (11)	0.3236 (4)	0.34787 (10)	0.0517 (5)
H10'	0.2927	0.4236	0.3187	0.062*
C10	0.74001 (12)	0.8395 (4)	0.34412 (9)	0.0489 (5)
H10	0.7475	0.9395	0.3153	0.059*
C11'	0.31458 (12)	0.3548 (5)	0.40558 (11)	0.0601 (6)
H11'	0.2870	0.4754	0.4149	0.072*
C11	0.77956 (13)	0.8707 (4)	0.40190 (10)	0.0567 (5)
H11	0.8128	0.9921	0.4119	0.068*
C12'	0.35180 (13)	0.2064 (5)	0.44909 (10)	0.0620 (6)
H12'	0.3492	0.2269	0.4878	0.074*
C12	0.76975 (13)	0.7205 (4)	0.44519 (10)	0.0597 (6)
H12	0.7965	0.7414	0.4843	0.072*
C13'	0.39265 (13)	0.0289 (4)	0.43557 (10)	0.0573 (6)
H13'	0.4176	−0.0697	0.4653	0.069*
C13	0.72101 (13)	0.5424 (4)	0.43057 (10)	0.0561 (6)
H13	0.7153	0.4424	0.4600	0.067*
C14'	0.39736 (10)	−0.0063 (3)	0.37744 (9)	0.0444 (4)
C14	0.67910 (12)	0.5061 (3)	0.37200 (9)	0.0459 (5)
C15'	0.44026 (11)	−0.1964 (4)	0.36283 (10)	0.0502 (5)
C15	0.62704 (12)	0.3163 (4)	0.35639 (10)	0.0503 (5)
C16	0.59013 (12)	0.2845 (4)	0.29960 (10)	0.0516 (5)
H16	0.5584	0.1591	0.2901	0.062*
C16'	0.44238 (12)	−0.2279 (4)	0.30675 (10)	0.0517 (5)
H16'	0.4684	−0.3534	0.2980	0.062*
C17'	0.48297 (13)	−0.3532 (4)	0.41088 (11)	0.0644 (6)
H17A	0.5035	−0.4779	0.3935	0.097*
H17B	0.4503	−0.4131	0.4328	0.097*
H17C	0.5223	−0.2686	0.4369	0.097*
C17	0.61402 (14)	0.1585 (4)	0.40359 (12)	0.0658 (7)
H17D	0.5801	0.0392	0.3856	0.099*
H17E	0.5935	0.2445	0.4304	0.099*
H17F	0.6602	0.0911	0.4248	0.099*
S1	0.51607 (4)	0.53496 (12)	0.07611 (3)	0.0620 (2)
S1'	0.38490 (4)	0.03471 (13)	0.08505 (3)	0.0655 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1'	0.0742 (16)	0.0787 (17)	0.0525 (13)	−0.0132 (14)	0.0075 (12)	0.0174 (12)
C1	0.0656 (14)	0.0640 (14)	0.0512 (12)	0.0067 (11)	0.0162 (10)	0.0135 (11)
C2	0.0656 (13)	0.0447 (11)	0.0494 (12)	−0.0016 (10)	0.0235 (10)	0.0059 (9)
C2'	0.0551 (12)	0.0461 (11)	0.0569 (13)	0.0003 (9)	0.0087 (10)	0.0039 (10)
C3	0.0492 (10)	0.0382 (9)	0.0471 (10)	0.0007 (8)	0.0218 (8)	0.0017 (8)
C3'	0.0431 (10)	0.0442 (10)	0.0451 (10)	−0.0050 (8)	0.0073 (8)	−0.0005 (8)
C4	0.0462 (10)	0.0438 (10)	0.0495 (11)	−0.0004 (8)	0.0171 (9)	−0.0004 (9)
C4'	0.0434 (10)	0.0489 (11)	0.0426 (10)	−0.0073 (8)	0.0103 (8)	−0.0040 (9)
C5	0.0506 (11)	0.0390 (10)	0.0594 (13)	−0.0073 (8)	0.0193 (10)	−0.0007 (9)
C5'	0.0480 (11)	0.0456 (11)	0.0548 (12)	0.0030 (9)	0.0130 (9)	−0.0045 (9)
C6'	0.0407 (10)	0.0410 (10)	0.0475 (11)	0.0008 (8)	0.0077 (8)	−0.0011 (8)
C6	0.0484 (10)	0.0378 (10)	0.0541 (12)	0.0000 (8)	0.0248 (9)	0.0038 (8)
C7	0.0473 (10)	0.0356 (9)	0.0466 (10)	0.0028 (8)	0.0232 (8)	0.0019 (8)
C7'	0.0368 (9)	0.0419 (10)	0.0416 (10)	−0.0029 (7)	0.0075 (7)	−0.0029 (8)
C8'	0.0467 (10)	0.0422 (10)	0.0483 (11)	0.0028 (8)	0.0105 (8)	−0.0032 (9)
C8	0.0555 (11)	0.0358 (9)	0.0447 (10)	−0.0065 (8)	0.0219 (9)	−0.0012 (8)
C9'	0.0379 (9)	0.0459 (10)	0.0449 (10)	−0.0017 (8)	0.0098 (8)	−0.0009 (8)
C9	0.0482 (10)	0.0391 (10)	0.0434 (10)	0.0057 (8)	0.0225 (8)	0.0021 (8)
C10'	0.0453 (10)	0.0554 (12)	0.0540 (12)	0.0048 (9)	0.0124 (9)	−0.0041 (10)
C10	0.0553 (11)	0.0482 (11)	0.0473 (11)	−0.0019 (9)	0.0208 (9)	0.0000 (9)
C11'	0.0498 (12)	0.0714 (15)	0.0624 (14)	0.0064 (11)	0.0205 (10)	−0.0104 (12)
C11	0.0562 (12)	0.0620 (13)	0.0537 (13)	0.0018 (11)	0.0178 (10)	−0.0061 (11)
C12'	0.0543 (12)	0.0867 (18)	0.0479 (12)	−0.0021 (12)	0.0187 (10)	−0.0068 (12)
C12	0.0649 (14)	0.0696 (15)	0.0446 (12)	0.0140 (12)	0.0145 (10)	−0.0021 (11)
C13'	0.0513 (12)	0.0740 (15)	0.0457 (12)	−0.0044 (11)	0.0113 (9)	0.0064 (11)
C13	0.0670 (14)	0.0600 (13)	0.0466 (12)	0.0194 (11)	0.0244 (10)	0.0099 (10)
C14'	0.0374 (9)	0.0502 (11)	0.0436 (10)	−0.0045 (8)	0.0072 (8)	0.0029 (9)
C14	0.0542 (11)	0.0428 (10)	0.0483 (11)	0.0135 (8)	0.0272 (9)	0.0082 (8)
C15'	0.0454 (10)	0.0468 (11)	0.0546 (12)	−0.0005 (9)	0.0060 (9)	0.0073 (9)
C15	0.0589 (12)	0.0428 (11)	0.0599 (13)	0.0107 (9)	0.0346 (10)	0.0149 (9)
C16	0.0565 (12)	0.0402 (10)	0.0648 (14)	−0.0026 (9)	0.0280 (10)	0.0101 (9)
C16'	0.0501 (11)	0.0443 (11)	0.0591 (13)	0.0091 (9)	0.0113 (9)	0.0001 (10)
C17'	0.0607 (14)	0.0607 (14)	0.0667 (15)	0.0089 (11)	0.0077 (11)	0.0168 (12)
C17	0.0743 (15)	0.0596 (14)	0.0740 (16)	0.0110 (12)	0.0380 (13)	0.0299 (12)
S1	0.0603 (4)	0.0672 (4)	0.0536 (4)	−0.0073 (3)	0.0061 (3)	0.0019 (3)
S1'	0.0684 (4)	0.0788 (4)	0.0530 (4)	−0.0042 (3)	0.0223 (3)	−0.0040 (3)

Geometric parameters (Å, º) top

C1'—C2'	1.310 (3)	C9'—C14'	1.417 (3)
C1'—S1'	1.725 (3)	C9—C10	1.407 (3)
C1'—H1'	0.9300	C9—C14	1.417 (3)
C1—C2	1.331 (3)	C10'—C11'	1.386 (3)
C1—S1	1.729 (3)	C10'—H10'	0.9300
C1—H1	0.9300	C10—C11	1.376 (3)
C2—C3	1.447 (3)	C10—H10	0.9300
C2—H2	0.9300	C11'—C12'	1.379 (3)
C2'—C3'	1.476 (3)	C11'—H11'	0.9300
C2'—H2'	0.9300	C11—C12	1.387 (3)
C3—C8	1.385 (3)	C11—H11	0.9300
C3—C4	1.419 (3)	C12'—C13'	1.371 (3)
C3'—C8'	1.398 (3)	C12'—H12'	0.9300
C3'—C4'	1.411 (3)	C12—C13	1.364 (4)
C4—C5	1.378 (3)	C12—H12	0.9300
C4—S1	1.737 (2)	C13'—C14'	1.404 (3)
C4'—C5'	1.373 (3)	C13'—H13'	0.9300
C4'—S1'	1.742 (2)	C13—C14	1.408 (3)
C5—C6	1.397 (3)	C13—H13	0.9300
C5—H5	0.9300	C14'—C15'	1.459 (3)
C5'—C6'	1.396 (3)	C14—C15	1.455 (3)
C5'—H5'	0.9300	C15'—C16'	1.339 (3)
C6'—C7'	1.419 (3)	C15'—C17'	1.507 (3)
C6'—C16'	1.444 (3)	C15—C16	1.343 (3)
C6—C7	1.426 (3)	C15—C17	1.507 (3)
C6—C16	1.441 (3)	C16—H16	0.9300
C7—C8	1.404 (3)	C16'—H16'	0.9300
C7—C9	1.457 (3)	C17'—H17A	0.9600
C7'—C8'	1.399 (3)	C17'—H17B	0.9600
C7'—C9'	1.461 (3)	C17'—H17C	0.9600
C8'—H8'	0.9300	C17—H17D	0.9600
C8—H8	0.9300	C17—H17E	0.9600
C9'—C10'	1.395 (3)	C17—H17F	0.9600

C2'—C1'—S1'	115.65 (19)	C11'—C10'—H10'	119.2
C2'—C1'—H1'	122.2	C9'—C10'—H10'	119.2
S1'—C1'—H1'	122.2	C11—C10—C9	121.5 (2)
C2—C1—S1	114.30 (17)	C11—C10—H10	119.3
C2—C1—H1	122.9	C9—C10—H10	119.3
S1—C1—H1	122.9	C12'—C11'—C10'	119.7 (2)
C1—C2—C3	112.4 (2)	C12'—C11'—H11'	120.1
C1—C2—H2	123.8	C10'—C11'—H11'	120.1
C3—C2—H2	123.8	C10—C11—C12	119.9 (2)
C1'—C2'—C3'	111.3 (2)	C10—C11—H11	120.1
C1'—C2'—H2'	124.3	C12—C11—H11	120.1
C3'—C2'—H2'	124.3	C13'—C12'—C11'	120.3 (2)
C8—C3—C4	119.30 (18)	C13'—C12'—H12'	119.8
C8—C3—C2	129.41 (19)	C11'—C12'—H12'	119.8
C4—C3—C2	111.29 (19)	C13—C12—C11	120.2 (2)
C8'—C3'—C4'	118.48 (18)	C13—C12—H12	119.9
C8'—C3'—C2'	130.0 (2)	C11—C12—H12	119.9
C4'—C3'—C2'	111.52 (19)	C12'—C13'—C14'	121.0 (2)
C5—C4—C3	121.2 (2)	C12'—C13'—H13'	119.5
C5—C4—S1	127.90 (17)	C14'—C13'—H13'	119.5
C3—C4—S1	110.93 (15)	C12—C13—C14	121.6 (2)
C5'—C4'—C3'	122.2 (2)	C12—C13—H13	119.2
C5'—C4'—S1'	127.17 (17)	C14—C13—H13	119.2
C3'—C4'—S1'	110.59 (15)	C13'—C14'—C9'	119.2 (2)
C4—C5—C6	119.36 (19)	C13'—C14'—C15'	121.09 (19)
C4—C5—H5	120.3	C9'—C14'—C15'	119.68 (19)
C6—C5—H5	120.3	C13—C14—C9	118.5 (2)
C4'—C5'—C6'	118.82 (19)	C13—C14—C15	121.65 (19)
C4'—C5'—H5'	120.6	C9—C14—C15	119.8 (2)
C6'—C5'—H5'	120.6	C16'—C15'—C14'	119.61 (19)
C5'—C6'—C7'	120.86 (18)	C16'—C15'—C17'	120.4 (2)
C5'—C6'—C16'	120.13 (18)	C14'—C15'—C17'	120.0 (2)
C7'—C6'—C16'	118.95 (18)	C16—C15—C14	119.40 (18)
C5—C6—C7	120.71 (18)	C16—C15—C17	120.3 (2)
C5—C6—C16	120.42 (19)	C14—C15—C17	120.3 (2)
C7—C6—C16	118.84 (19)	C15—C16—C6	123.3 (2)
C8—C7—C6	118.51 (19)	C15—C16—H16	118.4
C8—C7—C9	122.88 (18)	C6—C16—H16	118.4
C6—C7—C9	118.61 (17)	C15'—C16'—C6'	123.1 (2)
C8'—C7'—C6'	118.90 (18)	C15'—C16'—H16'	118.5
C8'—C7'—C9'	122.30 (18)	C6'—C16'—H16'	118.5
C6'—C7'—C9'	118.80 (17)	C15'—C17'—H17A	109.5
C3'—C8'—C7'	120.70 (19)	C15'—C17'—H17B	109.5
C3'—C8'—H8'	119.7	H17A—C17'—H17B	109.5
C7'—C8'—H8'	119.7	C15'—C17'—H17C	109.5
C3—C8—C7	120.92 (18)	H17A—C17'—H17C	109.5
C3—C8—H8	119.5	H17B—C17'—H17C	109.5
C7—C8—H8	119.5	C15—C17—H17D	109.5
C10'—C9'—C14'	118.04 (19)	C15—C17—H17E	109.5
C10'—C9'—C7'	122.22 (18)	H17D—C17—H17E	109.5
C14'—C9'—C7'	119.73 (18)	C15—C17—H17F	109.5
C10—C9—C14	118.38 (19)	H17D—C17—H17F	109.5
C10—C9—C7	121.69 (17)	H17E—C17—H17F	109.5
C14—C9—C7	119.93 (18)	C1—S1—C4	91.03 (11)
C11'—C10'—C9'	121.7 (2)	C1'—S1'—C4'	90.93 (12)

S1—C1—C2—C3	1.1 (3)	C6—C7—C9—C14	−3.5 (3)
S1'—C1'—C2'—C3'	−0.4 (3)	C14'—C9'—C10'—C11'	1.0 (3)
C1—C2—C3—C8	178.3 (2)	C7'—C9'—C10'—C11'	−178.1 (2)
C1—C2—C3—C4	−1.1 (3)	C14—C9—C10—C11	−1.4 (3)
C1'—C2'—C3'—C8'	179.8 (2)	C7—C9—C10—C11	178.70 (19)
C1'—C2'—C3'—C4'	0.6 (3)	C9'—C10'—C11'—C12'	−0.6 (4)
C8—C3—C4—C5	2.0 (3)	C9—C10—C11—C12	1.0 (3)
C2—C3—C4—C5	−178.43 (19)	C10'—C11'—C12'—C13'	0.2 (4)
C8—C3—C4—S1	−178.83 (15)	C10—C11—C12—C13	0.0 (3)
C2—C3—C4—S1	0.7 (2)	C11'—C12'—C13'—C14'	−0.2 (4)
C8'—C3'—C4'—C5'	−1.2 (3)	C11—C12—C13—C14	−0.5 (3)
C2'—C3'—C4'—C5'	178.05 (19)	C12'—C13'—C14'—C9'	0.6 (3)
C8'—C3'—C4'—S1'	−179.91 (15)	C12'—C13'—C14'—C15'	−179.4 (2)
C2'—C3'—C4'—S1'	−0.6 (2)	C10'—C9'—C14'—C13'	−0.9 (3)
C3—C4—C5—C6	−0.9 (3)	C7'—C9'—C14'—C13'	178.15 (18)
S1—C4—C5—C6	−179.89 (16)	C10'—C9'—C14'—C15'	179.06 (18)
C3'—C4'—C5'—C6'	0.3 (3)	C7'—C9'—C14'—C15'	−1.9 (3)
S1'—C4'—C5'—C6'	178.75 (16)	C12—C13—C14—C9	0.1 (3)
C4'—C5'—C6'—C7'	0.7 (3)	C12—C13—C14—C15	−179.93 (19)
C4'—C5'—C6'—C16'	−176.45 (19)	C10—C9—C14—C13	0.9 (3)
C4—C5—C6—C7	−1.0 (3)	C7—C9—C14—C13	−179.26 (17)
C4—C5—C6—C16	177.11 (19)	C10—C9—C14—C15	−179.12 (17)
C5—C6—C7—C8	1.8 (3)	C7—C9—C14—C15	0.8 (3)
C16—C6—C7—C8	−176.34 (18)	C13'—C14'—C15'—C16'	178.6 (2)
C5—C6—C7—C9	−178.46 (17)	C9'—C14'—C15'—C16'	−1.4 (3)
C16—C6—C7—C9	3.4 (3)	C13'—C14'—C15'—C17'	−2.5 (3)
C5'—C6'—C7'—C8'	−0.7 (3)	C9'—C14'—C15'—C17'	177.52 (19)
C16'—C6'—C7'—C8'	176.44 (18)	C13—C14—C15—C16	−177.8 (2)
C5'—C6'—C7'—C9'	179.81 (18)	C9—C14—C15—C16	2.2 (3)
C16'—C6'—C7'—C9'	−3.0 (3)	C13—C14—C15—C17	2.9 (3)
C4'—C3'—C8'—C7'	1.2 (3)	C9—C14—C15—C17	−177.15 (18)
C2'—C3'—C8'—C7'	−177.96 (19)	C14—C15—C16—C6	−2.3 (3)
C6'—C7'—C8'—C3'	−0.2 (3)	C17—C15—C16—C6	177.00 (19)
C9'—C7'—C8'—C3'	179.21 (17)	C5—C6—C16—C15	−178.7 (2)
C4—C3—C8—C7	−1.2 (3)	C7—C6—C16—C15	−0.5 (3)
C2—C3—C8—C7	179.37 (19)	C14'—C15'—C16'—C6'	2.4 (3)
C6—C7—C8—C3	−0.7 (3)	C17'—C15'—C16'—C6'	−176.44 (19)
C9—C7—C8—C3	179.61 (17)	C5'—C6'—C16'—C15'	177.0 (2)
C8'—C7'—C9'—C10'	3.6 (3)	C7'—C6'—C16'—C15'	−0.2 (3)
C6'—C7'—C9'—C10'	−176.94 (18)	C2—C1—S1—C4	−0.56 (19)
C8'—C7'—C9'—C14'	−175.43 (18)	C5—C4—S1—C1	178.9 (2)
C6'—C7'—C9'—C14'	4.0 (3)	C3—C4—S1—C1	−0.11 (16)
C8—C7—C9—C10	−3.9 (3)	C2'—C1'—S1'—C4'	0.0 (2)
C6—C7—C9—C10	176.38 (17)	C5'—C4'—S1'—C1'	−178.2 (2)
C8—C7—C9—C14	176.23 (17)	C3'—C4'—S1'—C1'	0.36 (16)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂S
M_r	248.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	18.7011 (10), 5.8199 (3), 23.4546 (14)
β (°)	105.158 (2)
V (Å³)	2463.9 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	31917, 6983, 4446
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.697

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.195, 1.06
No. of reflections	6983
No. of parameters	327
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.30

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y−1, z.

Acknowledgements

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

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gunasekaran, B., Dhayalan, V., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2010). Acta Cryst. E66, o1449. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar