4-(4-Meth­oxy­phen­yl)naphtho­[2,3-b]thio­phene

Vasudhevan, S.; Puthilibai, G.; Karunakaran, R.J.

doi:10.1107/S1600536812005697

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o875-o876

doi:10.1107/S1600536812005697

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4-(4-Methoxyphenyl)naphtho[2,3-b]thiophene

S. Vasudhevan,^a ^* G. Puthilibai ^b and R. Joel Karunakaran ^a ^*

^aDepartment of Chemistry, Madras Christian College (Autonomous), Chennai 600 059, Tamil Nadu, India, and ^bDepartment of Chemistry, Sri Sairam Engineering College, Chennai 600 044, Tamil Nadu, India
^*Correspondence e-mail: vasu_sbm@yahoo.com, rjkmcc@yahoo.com

(Received 16 January 2012; accepted 8 February 2012; online 29 February 2012)

In the title compound, C₁₉H₁₄OS, the naphthothiophene moiety is almost planar except for the S atom of the five-membered ring, which is situated 0.047 (6) Å out of the C₄ plane (with an r.m.s. deviation of fitted atoms = 0.0009 Å). The dihedral angle between the naphthothiophene plane and the attached methoxyphenyl ring is 67.6 (2)°. In the crystal, a C—H⋯π interaction is observed between a methoxyphenyl C—H group and the outer benzene ring of the naphthothiophene moiety. The five-membered ring of the naphthothiophene moiety is disordered, with the S and opposite non-fused C atom approximately exchanging positions, with a site-occupancy factors of 0.808 (3) and 0.187 (3).

Related literature

For related thiophene structures, see: Labat & Halfpenny (2005 ); Thenmozhi et al. (2008 ). For related heterocyclic compounds, see: Jones et al. (1984 ); Palani et al. (2006 ). For biological activity of naphthothiophenes, see: Zuse et al. (2007 , 2006 ); Dallemagne et al. (2003 ); Misra & Amin (1990 ).

Experimental

Crystal data

C₁₉H₁₄OS
M_r = 290.36
Monoclinic, P 2₁ /n
a = 9.2961 (5) Å
b = 15.9931 (7) Å
c = 10.0896 (6) Å
β = 104.580 (3)°
V = 1451.75 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.912, T_max = 0.961
15008 measured reflections
2553 independent reflections
2223 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.150
S = 1.11
2553 reflections
196 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the of C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯Cgⁱ	0.93	2.82	3.621 (3)	145
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005697/im2353sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005697/im2353Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005697/im2353Isup3.cml

checkCIF report

Comment top

Biological evaluation of benzo/naphtho thiophene heterocycles has shown them to act as potential antibiological agents. Naphtho[2,3-b]thiophene derivatives were found to exhibit antiproliferative activity related to inhibition of tubulin polymerization (Zuse et al. 2007, 2006). Five-membered heterocycles fused to cyclopenta[c]thiophene are investigated as new antitumor agents (Dallemagne et al. 2003). Benzo[b]naphtho[2,1-d]thiophene derivatives are found as potentially important metabolites (Misra & Amin, 1990).

Fig. 1 shows the ORTEP representation of the molecular structure of the title compound with atoms at the 40% probability level. The five membered ring of the naphtho-thiophene moiety is disordered with sulfur (S1) and carbon (C2) approximately exchanging positions. The two portions of the moiety were assigned variable occupancy factors during refinement with sum of their occupancies restrained as 1 resulting in a refined s.o.f. ratio of 81% and 19%. In the naphtho thiophene moiety, S1 of the five membered ring in the major component is observed 0.047 (6) Å out of the (C1–C4) plane (0.058 (7) Å for the minor component). The latter atoms show a r.m.s. deviation of 0.0009 Å or 0.009 Å for the major and minor component, respectively. The dihedral angle between the mean plane of the naphtho-thiophene moiety and the methoxy-phenyl ring is 67.6 (2)°. Fig. 2 shows the packing of molecules in the unit cell. There is a C—H···π interaction between H17 (symmcode: 1.5 - x, -0.5 + y, 1.5 - z) and the phenyl ring (C5–C10). The distance between the H atom and centroid of the phenyl ring is 2.822 Å. Except for this C—H···π interaction, the packing is featureless.

Related literature top

For related thiophene structures, see: Labat & Halfpenny (2005); Thenmozhi et al. (2008). For general background, see: Jones et al. (1984); Palani et al. (2006). For biological activity of naphthothiophenes, see: Zuse et al. (2007, 2006); Dallemagne et al. (2003); Misra & Amin (1990).

Experimental top

To a solution of (2-(acetoxy(4-methoxyphenyl)methyl)phenyl) (thiophen-2-yl)methylacetate (0.5 g, 1.12 mmol) in anhydrous dichloromethane (20 ml), BF₃ × Et₂O (40 mg) was added. The reaction mixture was then stirred at room temperature for 4 h under N₂ atmosphere. Removal of the solvent followed by column chromatography (n-hexane/ethylacetate 98:2) led to the isolation of the product 4-(4-methoxyphenyl)naphtho[2,3-b]thiophene (yield: 56%). The product was recrystallized from chloroform and was obtained as a colourless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP plot of the title compound with thermal ellipsoids drawn at the 40% probability level.
	Fig. 2. Molecular packing diagram. C—H···π interactions are shown as dotted lines.

4-(4-Methoxyphenyl)naphtho[2,3-b]thiophene top

Crystal data top

C₁₉H₁₄OS	F(000) = 608
M_r = 290.36	D_x = 1.328 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4322 reflections
a = 9.2961 (5) Å	θ = 2.7–24.5°
b = 15.9931 (7) Å	µ = 0.22 mm⁻¹
c = 10.0896 (6) Å	T = 293 K
β = 104.580 (3)°	Block, pale yellow
V = 1451.75 (13) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2553 independent reflections
Radiation source: fine-focus sealed tube	2223 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.912, T_max = 0.961	k = −19→19
15008 measured reflections	l = −11→11

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0618P)² + 1.0365P] where P = (F_o² + 2F_c²)/3
2553 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.33 e Å⁻³
4 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₁₄OS	V = 1451.75 (13) Å³
M_r = 290.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2961 (5) Å	µ = 0.22 mm⁻¹
b = 15.9931 (7) Å	T = 293 K
c = 10.0896 (6) Å	0.30 × 0.20 × 0.20 mm
β = 104.580 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2553 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2223 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.961	R_int = 0.024
15008 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	4 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.11	Δρ_max = 0.33 e Å⁻³
2553 reflections	Δρ_min = −0.35 e Å⁻³
196 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	Occ. (<1)
C1	0.5082 (5)	−0.0475 (3)	0.6960 (6)	0.0644 (14)	0.808 (3)
H1	0.4432	−0.0894	0.7079	0.077*	0.808 (3)
C2	0.6679 (6)	−0.0682 (3)	0.6871 (5)	0.0614 (3)	0.808 (3)
H2	0.7162	−0.1196	0.6943	0.074*	0.808 (3)
S1	0.45408 (12)	0.05754 (8)	0.68296 (10)	0.0614 (3)	0.808 (3)
C1'	0.461 (3)	−0.0280 (15)	0.677 (3)	0.0644 (14)	0.187 (3)
H1'	0.3766	−0.0550	0.6898	0.077*	0.187 (3)
C2'	0.4755 (15)	0.0563 (14)	0.646 (3)	0.0614 (3)	0.187 (3)
H2'	0.3939	0.0917	0.6199	0.074*	0.187 (3)
S1'	0.6213 (5)	−0.0676 (3)	0.6865 (5)	0.0614 (3)	0.187 (3)
C3	0.7222 (3)	0.01533 (15)	0.6642 (3)	0.0490 (6)
C4	0.8635 (3)	0.02564 (16)	0.6515 (3)	0.0515 (6)
H4	0.9258	−0.0204	0.6564	0.062*
C5	0.9148 (3)	0.10577 (17)	0.6308 (2)	0.0461 (6)
C6	1.0633 (3)	0.1195 (2)	0.6226 (3)	0.0605 (8)
H6	1.1268	0.0741	0.6279	0.073*
C7	1.1118 (3)	0.1930 (2)	0.6081 (3)	0.0631 (8)
H7	1.2106	0.1997	0.6059	0.076*
C8	1.0209 (3)	0.2633 (2)	0.5954 (3)	0.0630 (8)
H8	1.0603	0.3153	0.5833	0.076*
C9	0.8833 (3)	0.25843 (16)	0.6001 (2)	0.0452 (6)
H9	0.8252	0.3064	0.5910	0.054*
C10	0.8187 (3)	0.17623 (15)	0.6198 (2)	0.0407 (5)
C11	0.6717 (3)	0.16559 (15)	0.6331 (2)	0.0409 (5)
C12	0.6285 (3)	0.08554 (15)	0.6572 (2)	0.0437 (6)
C13	0.5697 (2)	0.23754 (15)	0.6292 (2)	0.0409 (5)
C14	0.5147 (3)	0.28478 (16)	0.5126 (3)	0.0484 (6)
H14	0.5416	0.2712	0.4325	0.058*
C15	0.4202 (3)	0.35206 (17)	0.5124 (3)	0.0490 (6)
H15	0.3842	0.3830	0.4328	0.059*
C16	0.3800 (3)	0.37276 (15)	0.6307 (2)	0.0426 (6)
C17	0.4321 (3)	0.32557 (16)	0.7474 (3)	0.0461 (6)
H17	0.4038	0.3387	0.8269	0.055*
C18	0.5258 (3)	0.25921 (16)	0.7463 (2)	0.0457 (6)
H18	0.5606	0.2281	0.8259	0.055*
C19	0.2441 (4)	0.4937 (2)	0.5322 (3)	0.0717 (9)
H19A	0.3303	0.5160	0.5086	0.107*
H19B	0.1878	0.5385	0.5576	0.107*
H19C	0.1838	0.4645	0.4548	0.107*
O1	0.2893 (2)	0.43755 (11)	0.64381 (19)	0.0548 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.057 (4)	0.077 (3)	0.056 (3)	−0.031 (2)	0.010 (3)	0.005 (2)
C2	0.0525 (6)	0.0696 (6)	0.0625 (7)	−0.0089 (4)	0.0150 (4)	0.0068 (5)
S1	0.0525 (6)	0.0696 (6)	0.0625 (7)	−0.0089 (4)	0.0150 (4)	0.0068 (5)
C1'	0.057 (4)	0.077 (3)	0.056 (3)	−0.031 (2)	0.010 (3)	0.005 (2)
C2'	0.0525 (6)	0.0696 (6)	0.0625 (7)	−0.0089 (4)	0.0150 (4)	0.0068 (5)
S1'	0.0525 (6)	0.0696 (6)	0.0625 (7)	−0.0089 (4)	0.0150 (4)	0.0068 (5)
C3	0.0631 (16)	0.0428 (14)	0.0391 (13)	0.0014 (12)	0.0091 (11)	0.0000 (10)
C4	0.0606 (16)	0.0466 (14)	0.0472 (14)	0.0126 (12)	0.0137 (12)	0.0023 (12)
C5	0.0438 (13)	0.0570 (15)	0.0371 (13)	0.0057 (11)	0.0094 (10)	−0.0017 (11)
C6	0.0478 (15)	0.080 (2)	0.0544 (17)	0.0155 (15)	0.0140 (12)	0.0006 (15)
C7	0.0409 (14)	0.084 (2)	0.0650 (18)	−0.0075 (14)	0.0153 (13)	−0.0171 (16)
C8	0.074 (2)	0.0624 (18)	0.0568 (17)	−0.0210 (15)	0.0235 (15)	−0.0096 (14)
C9	0.0533 (15)	0.0466 (14)	0.0373 (12)	0.0071 (11)	0.0145 (11)	−0.0074 (10)
C10	0.0422 (12)	0.0470 (13)	0.0331 (11)	−0.0018 (10)	0.0096 (9)	−0.0044 (10)
C11	0.0443 (13)	0.0436 (13)	0.0341 (12)	0.0007 (10)	0.0085 (10)	−0.0003 (10)
C12	0.0447 (13)	0.0463 (14)	0.0378 (12)	−0.0039 (11)	0.0062 (10)	0.0018 (10)
C13	0.0390 (12)	0.0432 (13)	0.0406 (13)	−0.0014 (10)	0.0101 (10)	0.0012 (10)
C14	0.0562 (15)	0.0538 (15)	0.0377 (13)	0.0060 (12)	0.0165 (11)	0.0018 (11)
C15	0.0533 (14)	0.0518 (15)	0.0405 (13)	0.0071 (12)	0.0091 (11)	0.0084 (11)
C16	0.0380 (12)	0.0423 (13)	0.0470 (14)	−0.0008 (10)	0.0100 (10)	−0.0010 (11)
C17	0.0497 (14)	0.0503 (14)	0.0408 (13)	0.0018 (11)	0.0162 (11)	−0.0008 (11)
C18	0.0496 (14)	0.0489 (14)	0.0383 (13)	0.0030 (11)	0.0105 (11)	0.0062 (11)
C19	0.081 (2)	0.0627 (19)	0.073 (2)	0.0271 (16)	0.0225 (17)	0.0152 (16)
O1	0.0584 (11)	0.0520 (11)	0.0562 (11)	0.0144 (9)	0.0185 (9)	0.0041 (9)

Geometric parameters (Å, º) top

C1—C2	1.545 (6)	C8—C9	1.294 (4)
C1—S1	1.749 (5)	C8—H8	0.9300
C1—H1	0.9300	C9—C10	1.479 (3)
C2—C3	1.468 (5)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.417 (3)
S1—C12	1.764 (3)	C11—C12	1.381 (3)
C1'—C2'	1.399 (10)	C11—C13	1.486 (3)
C1'—S1'	1.60 (3)	C13—C14	1.384 (3)
C1'—H1'	0.9300	C13—C18	1.387 (3)
C2'—C12	1.474 (10)	C14—C15	1.389 (4)
C2'—H2'	0.9300	C14—H14	0.9300
S1'—C3	1.673 (5)	C15—C16	1.378 (4)
C3—C4	1.362 (4)	C15—H15	0.9300
C3—C12	1.412 (4)	C16—O1	1.363 (3)
C4—C5	1.401 (4)	C16—C17	1.379 (3)
C4—H4	0.9300	C17—C18	1.375 (3)
C5—C6	1.420 (4)	C17—H17	0.9300
C5—C10	1.425 (3)	C18—H18	0.9300
C6—C7	1.281 (4)	C19—O1	1.419 (3)
C6—H6	0.9300	C19—H19A	0.9600
C7—C8	1.392 (4)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600

C2—C1—S1	117.7 (4)	C11—C10—C5	119.9 (2)
C2—C1—H1	121.2	C11—C10—C9	123.6 (2)
S1—C1—H1	121.2	C5—C10—C9	116.4 (2)
C3—C2—C1	100.8 (4)	C12—C11—C10	117.3 (2)
C3—C2—H2	129.6	C12—C11—C13	120.7 (2)
C1—C2—H2	129.6	C10—C11—C13	122.0 (2)
C1—S1—C12	89.8 (2)	C11—C12—C3	122.9 (2)
C2'—C1'—S1'	105 (2)	C11—C12—C2'	126.8 (10)
C2'—C1'—H1'	127.7	C3—C12—C2'	108.8 (10)
S1'—C1'—H1'	127.7	C11—C12—S1	125.5 (2)
C1'—C2'—C12	115.9 (19)	C3—C12—S1	111.67 (19)
C1'—C2'—H2'	122.1	C2'—C12—S1	13.0 (10)
C12—C2'—H2'	122.1	C14—C13—C18	117.6 (2)
C1'—S1'—C3	103.0 (9)	C14—C13—C11	122.8 (2)
C4—C3—C12	119.8 (2)	C18—C13—C11	119.6 (2)
C4—C3—C2	120.3 (3)	C13—C14—C15	121.5 (2)
C12—C3—C2	120.0 (3)	C13—C14—H14	119.2
C4—C3—S1'	134.1 (3)	C15—C14—H14	119.2
C12—C3—S1'	106.1 (3)	C16—C15—C14	119.6 (2)
C2—C3—S1'	13.9 (3)	C16—C15—H15	120.2
C3—C4—C5	119.8 (2)	C14—C15—H15	120.2
C3—C4—H4	120.1	O1—C16—C15	125.2 (2)
C5—C4—H4	120.1	O1—C16—C17	115.2 (2)
C4—C5—C6	121.5 (3)	C15—C16—C17	119.6 (2)
C4—C5—C10	120.3 (2)	C18—C17—C16	120.2 (2)
C6—C5—C10	118.2 (3)	C18—C17—H17	119.9
C7—C6—C5	121.6 (3)	C16—C17—H17	119.9
C7—C6—H6	119.2	C17—C18—C13	121.5 (2)
C5—C6—H6	119.2	C17—C18—H18	119.3
C6—C7—C8	121.9 (3)	C13—C18—H18	119.3
C6—C7—H7	119.1	O1—C19—H19A	109.5
C8—C7—H7	119.1	O1—C19—H19B	109.5
C9—C8—C7	122.1 (3)	H19A—C19—H19B	109.5
C9—C8—H8	119.0	O1—C19—H19C	109.5
C7—C8—H8	119.0	H19A—C19—H19C	109.5
C8—C9—C10	119.8 (2)	H19B—C19—H19C	109.5
C8—C9—H9	120.1	C16—O1—C19	118.1 (2)
C10—C9—H9	120.1

S1—C1—C2—C3	−1.9 (5)	C10—C11—C12—S1	177.76 (18)
C2—C1—S1—C12	2.4 (4)	C13—C11—C12—S1	1.0 (3)
S1'—C1'—C2'—C12	−11 (3)	C4—C3—C12—C11	2.2 (4)
C2'—C1'—S1'—C3	4 (2)	C2—C3—C12—C11	−178.7 (3)
C1—C2—C3—C4	179.4 (3)	S1'—C3—C12—C11	−177.1 (3)
C1—C2—C3—C12	0.2 (4)	C4—C3—C12—C2'	168.8 (11)
C1—C2—C3—S1'	−5.9 (12)	C2—C3—C12—C2'	−12.0 (11)
C1'—S1'—C3—C4	−174.8 (13)	S1'—C3—C12—C2'	−10.5 (11)
C1'—S1'—C3—C12	4.3 (13)	C4—C3—C12—S1	−177.7 (2)
C1'—S1'—C3—C2	179 (2)	C2—C3—C12—S1	1.4 (3)
C12—C3—C4—C5	−0.3 (4)	S1'—C3—C12—S1	3.0 (3)
C2—C3—C4—C5	−179.4 (3)	C1'—C2'—C12—C11	−179.4 (19)
S1'—C3—C4—C5	178.8 (3)	C1'—C2'—C12—C3	15 (3)
C3—C4—C5—C6	177.4 (2)	C1'—C2'—C12—S1	−90 (5)
C3—C4—C5—C10	−1.5 (4)	C1—S1—C12—C11	178.0 (3)
C4—C5—C6—C7	−177.8 (3)	C1—S1—C12—C3	−2.1 (3)
C10—C5—C6—C7	1.2 (4)	C1—S1—C12—C2'	78 (4)
C5—C6—C7—C8	−1.9 (5)	C12—C11—C13—C14	−116.0 (3)
C6—C7—C8—C9	1.2 (5)	C10—C11—C13—C14	67.3 (3)
C7—C8—C9—C10	0.2 (4)	C12—C11—C13—C18	63.7 (3)
C4—C5—C10—C11	1.5 (3)	C10—C11—C13—C18	−112.9 (3)
C6—C5—C10—C11	−177.4 (2)	C18—C13—C14—C15	0.7 (4)
C4—C5—C10—C9	179.2 (2)	C11—C13—C14—C15	−179.6 (2)
C6—C5—C10—C9	0.2 (3)	C13—C14—C15—C16	0.1 (4)
C8—C9—C10—C11	176.7 (2)	C14—C15—C16—O1	179.5 (2)
C8—C9—C10—C5	−0.9 (3)	C14—C15—C16—C17	−1.1 (4)
C5—C10—C11—C12	0.3 (3)	O1—C16—C17—C18	−179.3 (2)
C9—C10—C11—C12	−177.2 (2)	C15—C16—C17—C18	1.2 (4)
C5—C10—C11—C13	177.0 (2)	C16—C17—C18—C13	−0.4 (4)
C9—C10—C11—C13	−0.5 (3)	C14—C13—C18—C17	−0.5 (4)
C10—C11—C12—C3	−2.1 (3)	C11—C13—C18—C17	179.7 (2)
C13—C11—C12—C3	−178.9 (2)	C15—C16—O1—C19	−6.8 (4)
C10—C11—C12—C2'	−166.3 (12)	C17—C16—O1—C19	173.7 (3)
C13—C11—C12—C2'	17.0 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cgⁱ	0.93	2.82	3.621 (3)	145

Symmetry code: (i) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄OS
M_r	290.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.2961 (5), 15.9931 (7), 10.0896 (6)
β (°)	104.580 (3)
V (Å³)	1451.75 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.912, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	15008, 2553, 2223
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.150, 1.11
No. of reflections	2553
No. of parameters	196
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.35

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cgⁱ	0.93	2.822	3.621 (3)	145

Symmetry code: (i) x−1/2, −y+1/2, z+1/2.

Acknowledgements

The authors are grateful to the SAIF, IIT, Madras, Chennai, for the X-ray data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bruker (2004). APEX2. and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dallemagne, P., Khanh, L. P., Alsaïdi, A., Varlet, I., Collot, V., Paillet, M., Bureau, R. & Rault, S. (2003). Bioorg. Med. Chem. 11, 1161–1167. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jones, C. D., Jevnikar, M. G., Pike, A. J., Peters, M. K., Black, L. J., Thompson, A. R., Falcone, J. F. & Clemens, J. A. (1984). J. Med. Chem. 27, 1057–1066. CrossRef CAS PubMed Web of Science Google Scholar
Labat, G. & Halfpenny, J. (2005). Acta Cryst. E61, o2813–o2814. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Misra, B. & Amin, S. (1990). Chem. Res. Toxicol. 3(2), 93–97. CrossRef Web of Science Google Scholar
Palani, K., Amaladass, P., Mohanakrishnan, A. K. & Ponnuswamy, M. N. (2006). Acta Cryst. E62, o49–o51. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thenmozhi, S., SubbiahPandi, A., Ranjith, S., Clement, J. A. & MohanaKrishnan, A. K. (2008). Acta Cryst. E64, o2432. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zuse, A., Schmidt, P., Baasner, S., Böhm, K. J., Müller, K., Gerlach, M., Günther, E. G., Unger, E. & Prinz, H. (2006). J. Med. Chem. 49, 7816–7825. Web of Science CrossRef PubMed CAS Google Scholar
Zuse, A., Schmidt, P., Baasner, S., Böhm, K. J., Müller, K., Gerlach, M., Günther, E. G., Unger, E. & Prinz, H. (2007). J. Med. Chem. 50, 6059–6066. Web of Science CrossRef PubMed CAS Google Scholar