6-Phenyl-benzo[d]naphtho-[2,3-b]thio-phene.

In the title compound, C22H14S, the r.m.s. deviation from the mean plane of the four-fused-ring naphtho-thio-phene unit is 0.056 Å. The dihedral angle between the naphtho-thio-phene plane and the pendant phenyl ring is 67.24 (6)°. In the crystal, weak C-H⋯π and π-π stacking [minimum centroid-centroid separation = 3.7466 (10) Å] inter-actions are observed, which together lead to (010) sheets.

Related literature

For background to the biological activity of benzothio­phene derivatives, see: Isloora et al. (2010 ▶).

Experimental

Crystal data

C22H14S

M = 310.40

Orthorhombic,

a = 12.6752 (10) Å

b = 28.578 (2) Å

c = 8.5659 (6) Å

V = 3102.8 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

16518 measured reflections

3855 independent reflections

2892 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.03

3855 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012) ▶; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049471/hb6995sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049471/hb6995Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049471/hb6995Isup3.cml

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

C22H14S	F(000) = 1296
Mr = 310.40	Dx = 1.329 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 3855 reflections
a = 12.6752 (10) Å	θ = 1.8–28.4°
b = 28.578 (2) Å	µ = 0.21 mm−1
c = 8.5659 (6) Å	T = 293 K
V = 3102.8 (4) Å3	Block, colourless
Z = 8	0.20 × 0.20 × 0.20 mm

Bruker APEXII CCD diffractometer	2892 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.4°, θmin = 1.8°
ω and φ scans	h = −16→16
16518 measured reflections	k = −34→38
3855 independent reflections	l = −9→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.6864P] where P = (Fo2 + 2Fc2)/3
3855 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.24 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
S1	0.49436 (3)	0.039709 (15)	0.71196 (5)	0.04701 (14)
C11	0.34912 (11)	0.12197 (5)	1.10829 (17)	0.0367 (3)
C10	0.41403 (11)	0.14729 (5)	1.00101 (17)	0.0361 (3)
C17	0.52550 (12)	0.14890 (5)	0.75491 (18)	0.0375 (3)
C7	0.37407 (11)	0.05119 (5)	0.95979 (18)	0.0376 (3)
C9	0.46095 (11)	0.12338 (5)	0.87264 (17)	0.0361 (3)
C13	0.30387 (12)	0.14611 (6)	1.23609 (19)	0.0444 (4)
H13	0.2633	0.1297	1.3080	0.053*
C8	0.44145 (11)	0.07613 (5)	0.85662 (17)	0.0369 (3)
C22	0.62230 (13)	0.16834 (6)	0.7927 (2)	0.0471 (4)
H22	0.6492	0.1648	0.8930	0.057*
C1	0.42526 (12)	−0.00859 (5)	0.78516 (19)	0.0411 (3)
C6	0.36343 (12)	0.00252 (5)	0.91445 (18)	0.0388 (3)
C12	0.32950 (12)	0.07416 (5)	1.08341 (19)	0.0397 (3)
H12	0.2857	0.0579	1.1517	0.048*
C16	0.42662 (13)	0.19611 (6)	1.0261 (2)	0.0437 (4)
H16	0.4677	0.2134	0.9572	0.052*
C18	0.48824 (13)	0.15417 (6)	0.6039 (2)	0.0457 (4)
H18	0.4244	0.1406	0.5755	0.055*
C19	0.54498 (15)	0.17947 (7)	0.4950 (2)	0.0533 (4)
H19	0.5189	0.1832	0.3943	0.064*
C5	0.30009 (14)	−0.03191 (6)	0.9809 (2)	0.0491 (4)
H5	0.2582	−0.0250	1.0670	0.059*
C20	0.63982 (15)	0.19908 (6)	0.5357 (2)	0.0528 (4)
H20	0.6774	0.2166	0.4629	0.063*
C15	0.37981 (14)	0.21805 (6)	1.1489 (2)	0.0499 (4)
H15	0.3886	0.2501	1.1620	0.060*
C2	0.42771 (15)	−0.05383 (6)	0.7253 (2)	0.0493 (4)
H2	0.4712	−0.0614	0.6415	0.059*
C21	0.67926 (14)	0.19303 (6)	0.6823 (2)	0.0536 (4)
H21	0.7447	0.2056	0.7083	0.064*
C3	0.36430 (15)	−0.08691 (6)	0.7931 (2)	0.0539 (5)
H3	0.3645	−0.1173	0.7539	0.065*
C4	0.29989 (15)	−0.07614 (6)	0.9188 (2)	0.0554 (5)
H4	0.2563	−0.0990	0.9613	0.066*
C14	0.31846 (14)	0.19275 (6)	1.2558 (2)	0.0501 (4)
H14	0.2877	0.2080	1.3403	0.060*

	U11	U22	U33	U12	U13	U23
S1	0.0557 (3)	0.0449 (2)	0.0404 (3)	−0.00271 (18)	0.01194 (18)	−0.00246 (18)
C11	0.0346 (7)	0.0416 (8)	0.0341 (8)	0.0018 (6)	−0.0010 (6)	0.0011 (6)
C10	0.0347 (7)	0.0395 (8)	0.0340 (8)	0.0009 (6)	−0.0037 (6)	0.0022 (6)
C17	0.0415 (8)	0.0346 (8)	0.0365 (8)	0.0008 (6)	0.0039 (6)	0.0026 (6)
C7	0.0372 (7)	0.0384 (8)	0.0371 (8)	−0.0013 (6)	−0.0001 (6)	0.0039 (6)
C9	0.0355 (7)	0.0395 (8)	0.0333 (8)	−0.0024 (6)	−0.0016 (6)	0.0037 (6)
C13	0.0418 (8)	0.0510 (10)	0.0404 (9)	0.0017 (7)	0.0051 (7)	−0.0001 (7)
C8	0.0382 (7)	0.0394 (8)	0.0332 (8)	0.0001 (6)	0.0013 (6)	0.0010 (6)
C22	0.0508 (9)	0.0483 (9)	0.0423 (9)	−0.0087 (7)	−0.0026 (7)	0.0066 (8)
C1	0.0437 (8)	0.0392 (8)	0.0403 (9)	0.0014 (6)	−0.0038 (7)	0.0014 (7)
C6	0.0416 (8)	0.0356 (8)	0.0391 (8)	0.0010 (6)	−0.0025 (6)	0.0028 (6)
C12	0.0392 (7)	0.0410 (8)	0.0390 (8)	−0.0020 (6)	0.0050 (6)	0.0055 (7)
C16	0.0485 (8)	0.0392 (8)	0.0435 (9)	−0.0025 (7)	−0.0016 (7)	0.0033 (7)
C18	0.0454 (8)	0.0521 (10)	0.0397 (9)	−0.0004 (7)	0.0008 (7)	0.0042 (7)
C19	0.0608 (10)	0.0604 (11)	0.0386 (9)	0.0084 (9)	0.0052 (8)	0.0102 (8)
C5	0.0555 (10)	0.0402 (9)	0.0516 (10)	−0.0024 (7)	0.0069 (8)	0.0044 (7)
C20	0.0602 (10)	0.0450 (9)	0.0533 (11)	−0.0006 (8)	0.0188 (9)	0.0111 (8)
C15	0.0582 (10)	0.0401 (9)	0.0515 (10)	0.0023 (7)	−0.0028 (8)	−0.0043 (8)
C2	0.0580 (10)	0.0445 (9)	0.0454 (10)	0.0083 (8)	−0.0041 (8)	−0.0043 (8)
C21	0.0518 (9)	0.0504 (10)	0.0585 (11)	−0.0133 (8)	0.0052 (8)	0.0055 (9)
C3	0.0692 (11)	0.0344 (8)	0.0580 (11)	0.0036 (8)	−0.0092 (9)	−0.0027 (8)
C4	0.0653 (11)	0.0384 (9)	0.0625 (12)	−0.0048 (8)	0.0017 (9)	0.0067 (8)
C14	0.0538 (10)	0.0511 (10)	0.0455 (10)	0.0071 (8)	0.0040 (8)	−0.0098 (8)

S1—C1	1.7508 (16)	C12—H12	0.9300
S1—C8	1.7518 (15)	C16—C15	1.360 (2)
C11—C12	1.405 (2)	C16—H16	0.9300
C11—C13	1.415 (2)	C18—C19	1.382 (2)
C11—C10	1.430 (2)	C18—H18	0.9300
C10—C16	1.421 (2)	C19—C20	1.371 (3)
C10—C9	1.425 (2)	C19—H19	0.9300
C17—C22	1.385 (2)	C5—C4	1.372 (2)
C17—C18	1.385 (2)	C5—H5	0.9300
C17—C9	1.489 (2)	C20—C21	1.363 (3)
C7—C12	1.368 (2)	C20—H20	0.9300
C7—C8	1.421 (2)	C15—C14	1.402 (2)
C7—C6	1.450 (2)	C15—H15	0.9300
C9—C8	1.380 (2)	C2—C3	1.370 (3)
C13—C14	1.356 (2)	C2—H2	0.9300
C13—H13	0.9300	C21—H21	0.9300
C22—C21	1.383 (2)	C3—C4	1.386 (3)
C22—H22	0.9300	C3—H3	0.9300
C1—C2	1.391 (2)	C4—H4	0.9300
C1—C6	1.393 (2)	C14—H14	0.9300
C6—C5	1.392 (2)
C1—S1—C8	91.35 (7)	C15—C16—C10	121.39 (15)
C12—C11—C13	121.30 (14)	C15—C16—H16	119.3
C12—C11—C10	119.76 (13)	C10—C16—H16	119.3
C13—C11—C10	118.92 (14)	C19—C18—C17	120.63 (16)
C16—C10—C9	122.76 (14)	C19—C18—H18	119.7
C16—C10—C11	117.65 (14)	C17—C18—H18	119.7
C9—C10—C11	119.57 (13)	C20—C19—C18	119.93 (17)
C22—C17—C18	118.47 (14)	C20—C19—H19	120.0
C22—C17—C9	121.64 (14)	C18—C19—H19	120.0
C18—C17—C9	119.89 (14)	C4—C5—C6	119.59 (17)
C12—C7—C8	119.28 (14)	C4—C5—H5	120.2
C12—C7—C6	128.98 (14)	C6—C5—H5	120.2
C8—C7—C6	111.74 (13)	C21—C20—C19	120.25 (16)
C8—C9—C10	118.13 (13)	C21—C20—H20	119.9
C8—C9—C17	120.69 (14)	C19—C20—H20	119.9
C10—C9—C17	121.14 (13)	C16—C15—C14	120.59 (16)
C14—C13—C11	121.33 (16)	C16—C15—H15	119.7
C14—C13—H13	119.3	C14—C15—H15	119.7
C11—C13—H13	119.3	C3—C2—C1	118.14 (17)
C9—C8—C7	122.47 (14)	C3—C2—H2	120.9
C9—C8—S1	125.69 (12)	C1—C2—H2	120.9
C7—C8—S1	111.84 (11)	C20—C21—C22	120.21 (16)
C21—C22—C17	120.47 (16)	C20—C21—H21	119.9
C21—C22—H22	119.8	C22—C21—H21	119.9
C17—C22—H22	119.8	C2—C3—C4	121.47 (16)
C2—C1—C6	121.15 (15)	C2—C3—H3	119.3
C2—C1—S1	126.11 (13)	C4—C3—H3	119.3
C6—C1—S1	112.73 (12)	C5—C4—C3	120.33 (17)
C5—C6—C1	119.26 (15)	C5—C4—H4	119.8
C5—C6—C7	128.46 (15)	C3—C4—H4	119.8
C1—C6—C7	112.27 (13)	C13—C14—C15	120.07 (16)
C7—C12—C11	120.72 (14)	C13—C14—H14	120.0
C7—C12—H12	119.6	C15—C14—H14	120.0
C11—C12—H12	119.6
C12—C11—C10—C16	176.46 (14)	S1—C1—C6—C5	177.03 (13)
C13—C11—C10—C16	−2.1 (2)	C2—C1—C6—C7	178.72 (14)
C12—C11—C10—C9	−2.0 (2)	S1—C1—C6—C7	−1.81 (17)
C13—C11—C10—C9	179.41 (13)	C12—C7—C6—C5	4.2 (3)
C16—C10—C9—C8	−178.29 (14)	C8—C7—C6—C5	−176.05 (16)
C11—C10—C9—C8	0.1 (2)	C12—C7—C6—C1	−177.08 (15)
C16—C10—C9—C17	−0.9 (2)	C8—C7—C6—C1	2.66 (19)
C11—C10—C9—C17	177.53 (13)	C8—C7—C12—C11	0.5 (2)
C22—C17—C9—C8	−114.77 (18)	C6—C7—C12—C11	−179.82 (15)
C18—C17—C9—C8	66.1 (2)	C13—C11—C12—C7	−179.73 (14)
C22—C17—C9—C10	67.9 (2)	C10—C11—C12—C7	1.7 (2)
C18—C17—C9—C10	−111.22 (17)	C9—C10—C16—C15	179.23 (15)
C12—C11—C13—C14	−176.64 (16)	C11—C10—C16—C15	0.8 (2)
C10—C11—C13—C14	1.9 (2)	C22—C17—C18—C19	−2.0 (2)
C10—C9—C8—C7	2.1 (2)	C9—C17—C18—C19	177.19 (16)
C17—C9—C8—C7	−175.29 (14)	C17—C18—C19—C20	0.9 (3)
C10—C9—C8—S1	−177.76 (11)	C1—C6—C5—C4	0.3 (3)
C17—C9—C8—S1	4.8 (2)	C7—C6—C5—C4	178.93 (16)
C12—C7—C8—C9	−2.5 (2)	C18—C19—C20—C21	1.1 (3)
C6—C7—C8—C9	177.76 (14)	C10—C16—C15—C14	0.8 (3)
C12—C7—C8—S1	177.44 (12)	C6—C1—C2—C3	2.6 (2)
C6—C7—C8—S1	−2.33 (16)	S1—C1—C2—C3	−176.83 (13)
C1—S1—C8—C9	−178.97 (14)	C19—C20—C21—C22	−2.1 (3)
C1—S1—C8—C7	1.12 (12)	C17—C22—C21—C20	1.0 (3)
C18—C17—C22—C21	1.0 (3)	C1—C2—C3—C4	−0.6 (3)
C9—C17—C22—C21	−178.11 (16)	C6—C5—C4—C3	1.6 (3)
C8—S1—C1—C2	179.84 (15)	C2—C3—C4—C5	−1.5 (3)
C8—S1—C1—C6	0.41 (12)	C11—C13—C14—C15	−0.3 (3)
C2—C1—C6—C5	−2.4 (2)	C16—C15—C14—C13	−1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg2i	0.93	2.94	3.8138 (19)	158
C13—H13···Cg3i	0.93	2.64	3.5399 (17)	163

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1-C6 and C10–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg2i	0.93	2.94	3.8138 (19)	158
C13—H13⋯Cg3i	0.93	2.64	3.5399 (17)	163

Symmetry code: (i) .