4-(4-Meth-oxy-phen-yl)naphtho-[2,3-b]thio-phene.

In the title compound, C(19)H(14)OS, the naphtho-thio-phene moiety is almost planar except for the S atom of the five-membered ring, which is situated 0.047 (6) Å out of the C(4) plane (with an r.m.s. deviation of fitted atoms = 0.0009 Å). The dihedral angle between the naphtho-thio-phene plane and the attached meth-oxy-phenyl ring is 67.6 (2)°. In the crystal, a C-H⋯π inter-action is observed between a meth-oxy-phenyl C-H group and the outer benzene ring of the naphtho-thio-phene moiety. The five-membered ring of the naphtho-thio-phene 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 = 290.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.150

S = 1.11

2553 reflections

196 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.35 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005697/im2353sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812005697/im2353Isup3.cml

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

C19H14OS	F(000) = 608
Mr = 290.36	Dx = 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

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

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(Fo2) + (0.0618P)2 + 1.0365P] where P = (Fo2 + 2Fc2)/3
2553 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.33 e Å−3
4 restraints	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) .