10,11-Dihydro-diindeno[1,2-b:2',1'-d]thio-phene.

The title compound, C(18)H(12)S, comprises five fused rings forming an essentially planar mol-ecule, with a total puckering amplitude (Q) of 0.032 Å and a maximum deviation from the mean plane of 0.014 (4) Å for the C atoms of the methyl-ene groups. A crystallographic mirror plane orthogonal to the mol-ecular plane passes through the S atom and the midpoint of the opposite C-C bond within the central five-membered ring. The mol-ecules lie in layers, forming edge-to-face C-H⋯π inter-actions, with a separation of 2.66 Å between one H atom of the methyl-ene group and the centroid of an adjacent indene ring.

Related literature

For related synthetic chemistry and properties, see: Boberg et al. (1983 ▶, 1994 ▶); Baierweck et al. (1988 ▶). For related structures, see: Klebl et al. (2002 ▶); Wong et al. (2006 ▶). The puckering amplitude (Q) is defined by Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H12S

M = 260.34

Orthorhombic,

a = 8.3358 (6) Å

b = 26.3096 (17) Å

c = 5.6923 (3) Å

V = 1248.39 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 120 (2) K

0.26 × 0.15 × 0.01 mm

Data collection

Bruker–Nonius APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.940, T max = 0.998

7885 measured reflections

1461 independent reflections

1201 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.159

S = 1.07

1461 reflections

88 parameters

H-atom parameters constrained

Δρmax = 0.91 e Å−3

Δρmin = −0.34 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063684/bi2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063684/bi2268Isup2.hkl

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

C18H12S	F000 = 544
Mr = 260.34	Dx = 1.385 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 9689 reflections
a = 8.3358 (6) Å	θ = 2.9–27.5º
b = 26.3096 (17) Å	µ = 0.24 mm−1
c = 5.6923 (3) Å	T = 120 (2) K
V = 1248.39 (14) Å3	Plate, colourless
Z = 4	0.26 × 0.15 × 0.01 mm

Bruker–Nonius APEXII CCD diffractometer	1461 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1201 reflections with I > 2σ(I)
Monochromator: 10 cm confocal mirrors	Rint = 0.064
T = 120(2) K	θmax = 27.5º
φ and ω scans	θmin = 3.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	h = −10→10
Tmin = 0.940, Tmax = 0.998	k = −34→33
7885 measured reflections	l = −7→7

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0523P)2 + 2.4881P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.063	(Δ/σ)max < 0.001
wR(F2) = 0.159	Δρmax = 0.91 e Å−3
S = 1.07	Δρmin = −0.34 e Å−3
1461 reflections	Extinction correction: none
88 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.3662 (3)	0.29623 (9)	0.0799 (4)	0.0255 (5)
C2	0.2804 (3)	0.27680 (9)	−0.1063 (4)	0.0242 (5)
C3	0.2105 (3)	0.31895 (9)	−0.2498 (4)	0.0263 (5)
H3A	0.0917	0.3178	−0.2492	0.032*
H3B	0.2494	0.3178	−0.414	0.032*
C4	0.2733 (3)	0.36587 (10)	−0.1208 (4)	0.0266 (6)
C5	0.2502 (3)	0.41677 (10)	−0.1715 (5)	0.0319 (6)
H5	0.1889	0.4267	−0.3045	0.038*
C6	0.3182 (4)	0.45307 (10)	−0.0244 (5)	0.0340 (7)
H6	0.3034	0.4882	−0.0571	0.041*
C7	0.4073 (4)	0.43846 (10)	0.1690 (5)	0.0344 (7)
H7	0.4524	0.4639	0.2674	0.041*
C8	0.4327 (3)	0.38786 (10)	0.2235 (5)	0.0298 (6)
H8	0.4946	0.3783	0.3565	0.036*
C9	0.3650 (3)	0.35156 (9)	0.0778 (4)	0.0251 (5)
S1	0.45076 (12)	0.25	0.25580 (16)	0.0275 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0217 (12)	0.0301 (12)	0.0248 (12)	0.0012 (10)	0.0025 (10)	0.0004 (10)
C2	0.0216 (12)	0.0289 (13)	0.0222 (11)	0.0005 (10)	0.0020 (10)	0.0012 (10)
C3	0.0263 (13)	0.0323 (12)	0.0204 (11)	0.0013 (10)	−0.0030 (10)	0.0017 (10)
C4	0.0224 (12)	0.0317 (13)	0.0257 (12)	0.0000 (10)	0.0035 (10)	−0.0027 (10)
C5	0.0340 (15)	0.0338 (13)	0.0277 (13)	0.0035 (12)	0.0036 (11)	0.0034 (11)
C6	0.0383 (16)	0.0261 (12)	0.0377 (15)	0.0022 (12)	0.0068 (12)	0.0004 (11)
C7	0.0348 (16)	0.0309 (13)	0.0375 (15)	−0.0018 (11)	0.0047 (13)	−0.0054 (11)
C8	0.0259 (13)	0.0341 (13)	0.0293 (13)	−0.0004 (11)	0.0003 (11)	−0.0020 (11)
C9	0.0202 (12)	0.0309 (12)	0.0243 (12)	0.0017 (10)	0.0051 (10)	0.0008 (10)
S1	0.0278 (5)	0.0291 (5)	0.0254 (5)	0	−0.0065 (4)	0

C1—C2	1.377 (4)	C5—C6	1.391 (4)
C1—C9	1.456 (3)	C5—H5	0.950
C1—S1	1.726 (3)	C6—C7	1.383 (4)
C2—C2i	1.410 (5)	C6—H6	0.950
C2—C3	1.496 (3)	C7—C8	1.383 (4)
C3—C4	1.529 (3)	C7—H7	0.950
C3—H3A	0.990	C8—C9	1.385 (4)
C3—H3B	0.990	C8—H8	0.950
C4—C5	1.383 (4)	S1—C1i	1.726 (3)
C4—C9	1.415 (4)
C2—C1—C9	111.2 (2)	C4—C5—H5	120.6
C2—C1—S1	113.39 (19)	C6—C5—H5	120.6
C9—C1—S1	135.4 (2)	C7—C6—C5	120.5 (3)
C1—C2—C2i	111.79 (15)	C7—C6—H6	119.8
C1—C2—C3	110.3 (2)	C5—C6—H6	119.8
C2i—C2—C3	137.85 (13)	C6—C7—C8	121.9 (3)
C2—C3—C4	101.7 (2)	C6—C7—H7	119.1
C2—C3—H3A	111.4	C8—C7—H7	119.1
C4—C3—H3A	111.4	C7—C8—C9	117.9 (3)
C2—C3—H3B	111.4	C7—C8—H8	121.1
C4—C3—H3B	111.4	C9—C8—H8	121.1
H3A—C3—H3B	109.3	C8—C9—C4	121.0 (2)
C5—C4—C9	120.0 (2)	C8—C9—C1	133.0 (2)
C5—C4—C3	129.3 (2)	C4—C9—C1	106.0 (2)
C9—C4—C3	110.7 (2)	C1i—S1—C1	89.61 (17)
C4—C5—C6	118.8 (3)
C9—C1—C2—C2i	−179.91 (15)	C7—C8—C9—C4	0.2 (4)
S1—C1—C2—C2i	0.9 (2)	C7—C8—C9—C1	179.9 (3)
C9—C1—C2—C3	−1.0 (3)	C5—C4—C9—C8	−0.1 (4)
S1—C1—C2—C3	179.78 (18)	C3—C4—C9—C8	−179.2 (2)
C1—C2—C3—C4	1.5 (3)	C5—C4—C9—C1	−179.8 (2)
C2i—C2—C3—C4	179.98 (13)	C3—C4—C9—C1	1.0 (3)
C2—C3—C4—C5	179.4 (3)	C2—C1—C9—C8	−179.7 (3)
C2—C3—C4—C9	−1.5 (3)	S1—C1—C9—C8	−0.7 (5)
C9—C4—C5—C6	0.0 (4)	C2—C1—C9—C4	0.0 (3)
C3—C4—C5—C6	179.0 (3)	S1—C1—C9—C4	179.0 (2)
C4—C5—C6—C7	0.0 (4)	C2—C1—S1—C1i	−1.1 (3)
C5—C6—C7—C8	0.2 (4)	C9—C1—S1—C1i	179.9 (2)
C6—C7—C8—C9	−0.3 (4)