2-(9H-Fluoren-9-ylidenemeth-yl)thio-phene.

The title compound, C(18)H(12)S, contains a thio-phene ring which is disordered by rotation of 180° about the linking C-C bond. The site occupancies of the major and minor components of the disordered ring are 0.900 (3) and 0.100 (3), respectively. In one of these disordered components, the mol-ecule is stabilized by an intra-molecular C-H⋯S hydrogen bond. The compound was synthesized in good yield (80%) by a modified phase-transfer-catalysed condensation of fluorene with thio-phene-2-carbaldehyde.

Related literature

For a related structure, see: Fave et al., 2004 ▶. For related literature, see: Allen (2002 ▶); Lukeš et al. (2003 ▶); Mullen & Wegner (1998 ▶).

Experimental

Crystal data

C18H12S

M = 260.34

Orthorhombic,

a = 20.757 (4) Å

b = 44.434 (9) Å

c = 5.6260 (11) Å

V = 5189.0 (18) Å3

Z = 16

Mo Kα radiation

μ = 0.23 mm−1

T = 100 (2) K

0.57 × 0.13 × 0.08 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.938, T max = 0.985

11725 measured reflections

3018 independent reflections

1903 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.090

S = 0.99

3018 reflections

180 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1110 Friedel pairs

Flack parameter: −0.07 (8)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065099/fj2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065099/fj2086Isup2.hkl

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

C18H12S	F000 = 2176
Mr = 260.34	Dx = 1.333 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 4617 reflections
a = 20.757 (4) Å	θ = 3.7–29.1º
b = 44.434 (9) Å	µ = 0.23 mm−1
c = 5.6260 (11) Å	T = 100 (2) K
V = 5189.0 (18) Å3	Block, yellow
Z = 16	0.57 × 0.13 × 0.08 mm

Oxford Diffraction Gemini R CCD diffractometer	3018 independent reflections
Radiation source: fine-focus sealed tube	1903 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
T = 100(2) K	θmax = 29.1º
Rotation method data acquisition using ω and φ scans	θmin = 3.8º
Absorption correction: analytical(Clark & Reid, 1995)	h = −27→25
Tmin = 0.938, Tmax = 0.985	k = −59→58
11725 measured reflections	l = −7→7

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0485P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.15 e Å−3
3018 reflections	Δρmin = −0.17 e Å−3
180 parameters	Extinction correction: none
4 restraints	Absolute structure: Flack (1983), 1110 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.07 (8)
Secondary atom site location: difference Fourier map

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)

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	0.35040 (9)	0.03543 (4)	−0.1480 (3)	0.0504 (5)
C2	0.40287 (10)	0.01668 (4)	−0.1107 (4)	0.0605 (6)
H2A	0.4298	0.0194	0.0241	0.073*
C3	0.41552 (10)	−0.00616 (5)	−0.2727 (4)	0.0656 (6)
H3A	0.4516	−0.0189	−0.2475	0.079*
C4	0.37726 (11)	−0.01069 (5)	−0.4680 (4)	0.0640 (6)
H4A	0.3876	−0.0262	−0.5781	0.077*
C5	0.32362 (10)	0.00724 (4)	−0.5052 (4)	0.0594 (5)
H5A	0.2965	0.0040	−0.6387	0.071*
C6	0.31044 (9)	0.02985 (4)	−0.3442 (3)	0.0490 (5)
C7	0.25624 (9)	0.05093 (4)	−0.3394 (3)	0.0493 (5)
C8	0.20399 (10)	0.05396 (5)	−0.4884 (4)	0.0607 (5)
H8A	0.1994	0.0413	−0.6237	0.073*
C9	0.15827 (11)	0.07574 (5)	−0.4373 (4)	0.0670 (6)
H9A	0.1219	0.0780	−0.5380	0.080*
C10	0.16522 (10)	0.09415 (5)	−0.2405 (4)	0.0658 (6)
H10A	0.1334	0.1090	−0.2079	0.079*
C11	0.21746 (10)	0.09134 (5)	−0.0913 (4)	0.0608 (5)
H11A	0.2221	0.1043	0.0419	0.073*
C12	0.26339 (9)	0.06932 (4)	−0.1380 (3)	0.0490 (5)
C13	0.32372 (9)	0.06148 (4)	−0.0145 (3)	0.0490 (5)
C14	0.34399 (9)	0.07789 (4)	0.1761 (3)	0.0518 (5)
H14A	0.3125	0.0921	0.2256	0.062*
C15A	0.40114 (9)	0.07913 (4)	0.3214 (3)	0.0513 (5)	0.900 (3)
C18A	0.50774 (12)	0.07874 (5)	0.5125 (5)	0.0731 (7)	0.900 (3)
H18A	0.5513	0.0759	0.5592	0.088*	0.900 (3)
C17A	0.46607 (12)	0.09565 (5)	0.6332 (4)	0.0670 (6)	0.900 (3)
H17A	0.4767	0.1058	0.7767	0.080*	0.900 (3)
C16A	0.4056 (4)	0.0970 (4)	0.529 (3)	0.0747 (14)	0.900 (3)
H16A	0.3710	0.1087	0.5900	0.090*	0.900 (3)
S1A	0.47511 (8)	0.06280 (3)	0.26734 (16)	0.0755 (3)	0.900 (3)
C15B	0.40114 (9)	0.07913 (4)	0.3214 (3)	0.0513 (5)	0.100 (3)
C17B	0.46607 (12)	0.09565 (5)	0.6332 (4)	0.0670 (6)	0.100 (3)
H17B	0.4781	0.1058	0.7750	0.080*	0.100 (3)
C18B	0.50774 (12)	0.07874 (5)	0.5125 (5)	0.0731 (7)	0.100 (3)
H18B	0.5512	0.0758	0.5602	0.088*	0.100 (3)
C16B	0.481 (3)	0.0659 (10)	0.311 (4)	0.0755 (3)	0.100 (3)
H16B	0.5013	0.0532	0.1960	0.091*	0.100 (3)
S1B	0.3980 (11)	0.0978 (10)	0.532 (7)	0.0747 (14)	0.100 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0532 (11)	0.0451 (11)	0.0528 (11)	−0.0072 (9)	0.0047 (9)	−0.0017 (9)
C2	0.0557 (12)	0.0503 (12)	0.0754 (13)	−0.0021 (10)	−0.0032 (11)	−0.0117 (11)
C3	0.0575 (12)	0.0517 (12)	0.0874 (16)	0.0001 (10)	0.0055 (12)	−0.0126 (12)
C4	0.0699 (14)	0.0503 (13)	0.0717 (13)	−0.0051 (11)	0.0093 (13)	−0.0153 (12)
C5	0.0684 (13)	0.0544 (12)	0.0555 (11)	−0.0128 (10)	0.0014 (11)	−0.0072 (11)
C6	0.0570 (11)	0.0428 (11)	0.0473 (10)	−0.0082 (9)	0.0039 (10)	−0.0004 (9)
C7	0.0542 (11)	0.0438 (11)	0.0500 (11)	−0.0054 (9)	0.0035 (9)	0.0041 (10)
C8	0.0657 (13)	0.0608 (13)	0.0557 (10)	−0.0042 (11)	−0.0049 (12)	0.0017 (11)
C9	0.0649 (14)	0.0688 (15)	0.0673 (15)	−0.0031 (11)	−0.0130 (11)	0.0128 (12)
C10	0.0643 (13)	0.0580 (13)	0.0750 (14)	0.0076 (10)	−0.0009 (12)	0.0077 (13)
C11	0.0671 (13)	0.0519 (12)	0.0634 (12)	0.0033 (10)	0.0028 (12)	−0.0026 (11)
C12	0.0520 (11)	0.0468 (10)	0.0483 (11)	−0.0047 (9)	0.0057 (8)	0.0018 (9)
C13	0.0528 (10)	0.0461 (10)	0.0482 (11)	−0.0072 (9)	0.0042 (9)	0.0000 (9)
C14	0.0555 (11)	0.0487 (11)	0.0513 (11)	−0.0028 (9)	0.0087 (9)	−0.0005 (9)
C15A	0.0598 (12)	0.0461 (11)	0.0480 (11)	−0.0100 (9)	−0.0005 (9)	0.0023 (9)
C18A	0.0757 (15)	0.0666 (15)	0.0771 (14)	−0.0061 (12)	−0.0193 (14)	0.0019 (14)
C17A	0.0865 (16)	0.0614 (14)	0.0531 (12)	−0.0118 (13)	−0.0108 (12)	−0.0052 (12)
C16A	0.082 (3)	0.0744 (16)	0.0680 (12)	−0.022 (2)	−0.005 (2)	0.0022 (11)
S1A	0.0667 (6)	0.0868 (6)	0.0731 (5)	0.0098 (4)	−0.0143 (4)	−0.0252 (5)
C15B	0.0598 (12)	0.0461 (11)	0.0480 (11)	−0.0100 (9)	−0.0005 (9)	0.0023 (9)
C17B	0.0865 (16)	0.0614 (14)	0.0531 (12)	−0.0118 (13)	−0.0108 (12)	−0.0052 (12)
C18B	0.0757 (15)	0.0666 (15)	0.0771 (14)	−0.0061 (12)	−0.0193 (14)	0.0019 (14)
C16B	0.0667 (6)	0.0868 (6)	0.0731 (5)	0.0098 (4)	−0.0143 (4)	−0.0252 (5)
S1B	0.082 (3)	0.0744 (16)	0.0680 (12)	−0.022 (2)	−0.005 (2)	0.0022 (11)

C1—C2	1.387 (3)	C10—C11	1.377 (3)
C1—C6	1.403 (3)	C10—H10A	0.9500
C1—C13	1.487 (3)	C11—C12	1.391 (3)
C2—C3	1.389 (3)	C11—H11A	0.9500
C2—H2A	0.9500	C12—C13	1.474 (3)
C3—C4	1.371 (3)	C13—C14	1.363 (3)
C3—H3A	0.9500	C14—C15A	1.442 (3)
C4—C5	1.385 (3)	C14—H14A	0.9500
C4—H4A	0.9500	C15A—C16A	1.416 (19)
C5—C6	1.380 (3)	C15A—S1A	1.725 (3)
C5—H5A	0.9500	C18A—C17A	1.332 (3)
C6—C7	1.464 (3)	C18A—S1A	1.692 (3)
C7—C8	1.377 (3)	C18A—H18A	0.9500
C7—C12	1.405 (3)	C17A—C16A	1.388 (3)
C8—C9	1.386 (3)	C17A—H17A	0.9500
C8—H8A	0.9500	C16A—H16A	0.9500
C9—C10	1.384 (3)	C16B—H16B	0.9500
C9—H9A	0.9500
C2—C1—C6	118.53 (18)	C11—C10—H10A	119.5
C2—C1—C13	133.10 (18)	C9—C10—H10A	119.5
C6—C1—C13	108.35 (17)	C10—C11—C12	119.2 (2)
C1—C2—C3	119.2 (2)	C10—C11—H11A	120.4
C1—C2—H2A	120.4	C12—C11—H11A	120.4
C3—C2—H2A	120.4	C11—C12—C7	119.26 (19)
C4—C3—C2	121.6 (2)	C11—C12—C13	131.25 (18)
C4—C3—H3A	119.2	C7—C12—C13	109.45 (17)
C2—C3—H3A	119.2	C14—C13—C12	120.45 (17)
C3—C4—C5	120.2 (2)	C14—C13—C1	134.33 (19)
C3—C4—H4A	119.9	C12—C13—C1	105.19 (16)
C5—C4—H4A	119.9	C13—C14—C15A	136.09 (18)
C6—C5—C4	118.6 (2)	C13—C14—H14A	112.0
C6—C5—H5A	120.7	C15A—C14—H14A	112.0
C4—C5—H5A	120.7	C16A—C15A—C14	122.8 (4)
C5—C6—C1	121.84 (18)	C16A—C15A—S1A	108.9 (4)
C5—C6—C7	129.06 (17)	C14—C15A—S1A	128.03 (14)
C1—C6—C7	109.09 (16)	C17A—C18A—S1A	113.1 (2)
C8—C7—C12	121.16 (18)	C17A—C18A—H18A	123.5
C8—C7—C6	131.03 (19)	S1A—C18A—H18A	123.5
C12—C7—C6	107.78 (17)	C18A—C17A—C16A	113.4 (9)
C7—C8—C9	118.8 (2)	C18A—C17A—H17A	123.3
C7—C8—H8A	120.6	C16A—C17A—H17A	123.3
C9—C8—H8A	120.6	C17A—C16A—C15A	112.5 (12)
C10—C9—C8	120.5 (2)	C17A—C16A—H16A	123.8
C10—C9—H9A	119.8	C15A—C16A—H16A	123.8
C8—C9—H9A	119.8	C18A—S1A—C15A	92.08 (13)
C11—C10—C9	121.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···S1A	0.95	2.55	3.311 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯S1A	0.95	2.55	3.311 (4)	139