3,9'-Bi(9H-fluorene).

THE TITLE COMPOUND [SYSTEMATIC NAME: 9-(9H-fluoren-3-yl)-9H-fluorene], C(26)H(18), was obtained unintentionally as the product of the synthesis of a compound based on fluorene-thio-phene units. The two fluorene rings are connected through C atoms in the 3- and 9'-positions, and the dihedral angle between the mean planes of the two fluorene units is 78.57 (6)°.

Related literature

For the crystal structures of related compounds, see: Dougherty et al. (1978 ▶); Sridevi et al. (2006 ▶). For the synthesis of the compound, see: Stille et al. (1993 ▶, 1998 ▶); Grasa & Nolan (2001 ▶). For the inter­molecular C—H⋯π inter­actions, see: Tsuzuki et al. (2000 ▶); Nishio (2004 ▶).

Experimental

Crystal data

C26H18

M = 330.40

Orthorhombic,

a = 6.22600 (1) Å

b = 8.3968 (2) Å

c = 33.5357 (7) Å

V = 1753.20 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.45 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.969, T max = 0.989

15454 measured reflections

2352 independent reflections

2014 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.04

2352 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024841/zj2080sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024841/zj2080Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024841/zj2080Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812024841/zj2080Isup4.cml

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

C26H18	F(000) = 696
Mr = 330.40	Dx = 1.252 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac2ab	Cell parameters from 5140 reflections
a = 6.22600 (1) Å	θ = 2.4–24.1°
b = 8.3968 (2) Å	µ = 0.07 mm−1
c = 33.5357 (7) Å	T = 293 K
V = 1753.20 (6) Å3	Prism, colourless
Z = 4	0.45 × 0.22 × 0.16 mm

Bruker APEXII CCD area-detector diffractometer	2352 independent reflections
Radiation source: fine-focus sealed tube	2014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (APEX2; Bruker,2005)	h = −8→8
Tmin = 0.969, Tmax = 0.989	k = −10→9
15454 measured reflections	l = −43→43

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.1328P] where P = (Fo2 + 2Fc2)/3
2352 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.14 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
C1	0.6920 (3)	0.3409 (2)	0.20770 (5)	0.0533 (5)
H1	0.6063	0.2764	0.1917	0.064*
C2	0.8720 (4)	0.4144 (2)	0.19215 (5)	0.0578 (5)
H2	0.9063	0.4002	0.1654	0.069*
C3	1.0021 (3)	0.5087 (3)	0.21587 (5)	0.0581 (5)
H3	1.1234	0.5565	0.2050	0.070*
C4	0.9531 (3)	0.5326 (2)	0.25577 (5)	0.0503 (4)
H4	1.0414	0.5950	0.2718	0.060*
C5	0.7212 (3)	0.5705 (2)	0.34358 (4)	0.0424 (4)
H5	0.8501	0.6264	0.3441	0.051*
C6	0.5806 (3)	0.5777 (2)	0.37597 (5)	0.0451 (4)
C7	0.3899 (3)	0.4923 (3)	0.37462 (5)	0.0572 (5)
H7	0.2957	0.4980	0.3961	0.069*
C8	0.3361 (3)	0.3984 (3)	0.34195 (5)	0.0599 (5)
H8	0.2081	0.3413	0.3416	0.072*
C9	0.4518 (3)	0.3053 (2)	0.27093 (5)	0.0527 (5)
H9A	0.4584	0.1908	0.2746	0.063*
H9B	0.3175	0.3326	0.2579	0.063*
C10	0.6411 (3)	0.36460 (19)	0.24736 (5)	0.0445 (4)
C11	0.7703 (3)	0.46193 (19)	0.27133 (4)	0.0409 (4)
C12	0.6660 (3)	0.47883 (19)	0.31054 (4)	0.0394 (4)
C13	0.4749 (3)	0.3913 (2)	0.31014 (5)	0.0457 (4)
C1'	0.6708 (4)	0.9656 (3)	0.38487 (6)	0.0685 (6)
H1'	0.5425	0.9613	0.3707	0.082*
C2'	0.7935 (6)	1.1033 (3)	0.38502 (7)	0.0870 (9)
H2'	0.7461	1.1922	0.3710	0.104*
C3'	0.9840 (6)	1.1101 (3)	0.40558 (7)	0.0895 (9)
H3'	1.0644	1.2035	0.4051	0.107*
C4'	1.0581 (4)	0.9809 (3)	0.42685 (6)	0.0748 (7)
H4'	1.1876	0.9861	0.4406	0.090*
C5'	1.1220 (4)	0.6453 (3)	0.47611 (6)	0.0678 (6)
H5'	1.2371	0.7117	0.4821	0.081*
C6'	1.1042 (5)	0.4983 (3)	0.49389 (6)	0.0810 (7)
H6'	1.2075	0.4656	0.5122	0.097*
C7'	0.9355 (5)	0.3993 (3)	0.48493 (6)	0.0841 (8)
H7'	0.9269	0.2998	0.4970	0.101*
C8'	0.7779 (4)	0.4454 (3)	0.45821 (5)	0.0665 (6)
H8'	0.6643	0.3776	0.4522	0.080*
C9'	0.6353 (3)	0.6749 (2)	0.41279 (5)	0.0484 (4)
H9'	0.5018	0.6934	0.4276	0.058*
C10'	0.7422 (3)	0.8349 (2)	0.40610 (5)	0.0514 (5)
C11'	0.9357 (3)	0.8430 (2)	0.42730 (5)	0.0539 (5)
C12'	0.9652 (3)	0.6932 (2)	0.44908 (5)	0.0512 (5)
C13'	0.7921 (3)	0.5934 (2)	0.44068 (4)	0.0486 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0685 (12)	0.0461 (10)	0.0453 (9)	0.0044 (10)	−0.0133 (9)	−0.0061 (8)
C2	0.0726 (12)	0.0581 (11)	0.0425 (9)	0.0099 (11)	0.0001 (9)	−0.0040 (8)
C3	0.0576 (11)	0.0652 (12)	0.0515 (10)	0.0027 (11)	0.0064 (8)	−0.0017 (9)
C4	0.0454 (9)	0.0568 (10)	0.0487 (9)	−0.0012 (9)	−0.0007 (7)	−0.0064 (8)
C5	0.0395 (8)	0.0459 (9)	0.0418 (8)	−0.0055 (8)	−0.0037 (7)	−0.0027 (7)
C6	0.0460 (9)	0.0486 (10)	0.0406 (8)	−0.0027 (8)	−0.0032 (7)	0.0011 (7)
C7	0.0518 (10)	0.0723 (13)	0.0474 (9)	−0.0129 (11)	0.0049 (8)	−0.0008 (9)
C8	0.0533 (11)	0.0703 (13)	0.0560 (10)	−0.0224 (11)	−0.0015 (9)	0.0000 (9)
C9	0.0563 (10)	0.0489 (10)	0.0527 (9)	−0.0080 (9)	−0.0127 (9)	−0.0048 (8)
C10	0.0519 (9)	0.0358 (8)	0.0457 (8)	0.0059 (8)	−0.0106 (7)	0.0003 (7)
C11	0.0444 (8)	0.0365 (8)	0.0417 (8)	0.0053 (8)	−0.0071 (7)	−0.0017 (7)
C12	0.0402 (8)	0.0372 (8)	0.0409 (8)	0.0011 (7)	−0.0052 (6)	0.0010 (7)
C13	0.0477 (9)	0.0439 (9)	0.0456 (8)	−0.0082 (9)	−0.0078 (7)	0.0014 (7)
C1'	0.0966 (17)	0.0588 (12)	0.0499 (10)	0.0056 (14)	0.0028 (11)	−0.0061 (9)
C2'	0.148 (3)	0.0539 (13)	0.0587 (13)	−0.0025 (18)	0.0172 (16)	−0.0040 (11)
C3'	0.141 (3)	0.0634 (15)	0.0643 (13)	−0.0384 (18)	0.0314 (17)	−0.0150 (12)
C4'	0.0866 (15)	0.0826 (16)	0.0553 (11)	−0.0337 (15)	0.0164 (11)	−0.0219 (12)
C5'	0.0586 (11)	0.0961 (17)	0.0488 (10)	0.0035 (13)	−0.0035 (9)	−0.0247 (12)
C6'	0.0970 (17)	0.0944 (18)	0.0515 (11)	0.0283 (17)	−0.0225 (12)	−0.0155 (13)
C7'	0.130 (2)	0.0692 (14)	0.0530 (11)	0.0115 (17)	−0.0230 (14)	−0.0030 (11)
C8'	0.0916 (16)	0.0617 (12)	0.0463 (9)	−0.0063 (13)	−0.0088 (11)	−0.0038 (9)
C9'	0.0479 (9)	0.0566 (11)	0.0406 (8)	−0.0019 (9)	0.0039 (7)	−0.0064 (8)
C10'	0.0649 (12)	0.0515 (10)	0.0379 (8)	−0.0024 (10)	0.0085 (8)	−0.0105 (8)
C11'	0.0619 (11)	0.0610 (11)	0.0389 (8)	−0.0110 (10)	0.0108 (8)	−0.0151 (8)
C12'	0.0499 (10)	0.0679 (12)	0.0359 (7)	−0.0042 (10)	0.0060 (7)	−0.0145 (8)
C13'	0.0566 (10)	0.0562 (10)	0.0330 (7)	−0.0004 (9)	0.0022 (7)	−0.0087 (7)

C1—C2	1.382 (3)	C1'—C10'	1.382 (3)
C1—C10	1.382 (2)	C1'—C2'	1.385 (4)
C1—H1	0.9300	C1'—H1'	0.9300
C2—C3	1.384 (3)	C2'—C3'	1.374 (4)
C2—H2	0.9300	C2'—H2'	0.9300
C3—C4	1.387 (2)	C3'—C4'	1.378 (4)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C11	1.386 (2)	C4'—C11'	1.387 (3)
C4—H4	0.9300	C4'—H4'	0.9300
C5—C12	1.392 (2)	C5'—C6'	1.375 (4)
C5—C6	1.396 (2)	C5'—C12'	1.392 (3)
C5—H5	0.9300	C5'—H5'	0.9300
C6—C7	1.388 (3)	C6'—C7'	1.373 (4)
C6—C9'	1.519 (2)	C6'—H6'	0.9300
C7—C8	1.391 (3)	C7'—C8'	1.384 (3)
C7—H7	0.9300	C7'—H7'	0.9300
C8—C13	1.374 (3)	C8'—C13'	1.378 (3)
C8—H8	0.9300	C8'—H8'	0.9300
C9—C10	1.504 (2)	C9'—C13'	1.515 (2)
C9—C13	1.507 (2)	C9'—C10'	1.516 (3)
C9—H9A	0.9700	C9'—H9'	0.9800
C9—H9B	0.9700	C10'—C11'	1.401 (3)
C10—C11	1.400 (2)	C11'—C12'	1.466 (3)
C11—C12	1.473 (2)	C12'—C13'	1.394 (3)
C12—C13	1.399 (2)
C2—C1—C10	119.00 (17)	C10'—C1'—C2'	118.9 (2)
C2—C1—H1	120.5	C10'—C1'—H1'	120.5
C10—C1—H1	120.5	C2'—C1'—H1'	120.5
C1—C2—C3	120.87 (17)	C3'—C2'—C1'	120.9 (3)
C1—C2—H2	119.6	C3'—C2'—H2'	119.6
C3—C2—H2	119.6	C1'—C2'—H2'	119.6
C2—C3—C4	120.59 (18)	C2'—C3'—C4'	121.1 (2)
C2—C3—H3	119.7	C2'—C3'—H3'	119.5
C4—C3—H3	119.7	C4'—C3'—H3'	119.5
C11—C4—C3	118.81 (18)	C3'—C4'—C11'	118.6 (2)
C11—C4—H4	120.6	C3'—C4'—H4'	120.7
C3—C4—H4	120.6	C11'—C4'—H4'	120.7
C12—C5—C6	119.22 (15)	C6'—C5'—C12'	119.1 (2)
C12—C5—H5	120.4	C6'—C5'—H5'	120.5
C6—C5—H5	120.4	C12'—C5'—H5'	120.5
C7—C6—C5	119.27 (15)	C7'—C6'—C5'	120.7 (2)
C7—C6—C9'	119.73 (16)	C7'—C6'—H6'	119.7
C5—C6—C9'	120.99 (15)	C5'—C6'—H6'	119.7
C6—C7—C8	121.63 (17)	C6'—C7'—C8'	121.0 (2)
C6—C7—H7	119.2	C6'—C7'—H7'	119.5
C8—C7—H7	119.2	C8'—C7'—H7'	119.5
C13—C8—C7	119.00 (17)	C13'—C8'—C7'	118.9 (2)
C13—C8—H8	120.5	C13'—C8'—H8'	120.6
C7—C8—H8	120.5	C7'—C8'—H8'	120.6
C10—C9—C13	103.00 (14)	C13'—C9'—C10'	102.05 (15)
C10—C9—H9A	111.2	C13'—C9'—C6	113.82 (15)
C13—C9—H9A	111.2	C10'—C9'—C6	117.03 (14)
C10—C9—H9B	111.2	C13'—C9'—H9'	107.8
C13—C9—H9B	111.2	C10'—C9'—H9'	107.8
H9A—C9—H9B	109.1	C6—C9'—H9'	107.8
C1—C10—C11	120.33 (17)	C1'—C10'—C11'	120.0 (2)
C1—C10—C9	129.63 (17)	C1'—C10'—C9'	129.7 (2)
C11—C10—C9	109.98 (14)	C11'—C10'—C9'	110.21 (17)
C4—C11—C10	120.37 (15)	C4'—C11'—C10'	120.5 (2)
C4—C11—C12	131.06 (15)	C4'—C11'—C12'	130.8 (2)
C10—C11—C12	108.38 (15)	C10'—C11'—C12'	108.59 (17)
C5—C12—C13	120.54 (15)	C5'—C12'—C13'	120.0 (2)
C5—C12—C11	130.90 (15)	C5'—C12'—C11'	131.35 (19)
C13—C12—C11	108.41 (14)	C13'—C12'—C11'	108.56 (16)
C8—C13—C12	120.32 (16)	C8'—C13'—C12'	120.38 (19)
C8—C13—C9	129.64 (16)	C8'—C13'—C9'	128.99 (19)
C12—C13—C9	109.97 (15)	C12'—C13'—C9'	110.59 (16)
C10—C1—C2—C3	0.9 (3)	C12'—C5'—C6'—C7'	0.6 (3)
C1—C2—C3—C4	−0.6 (3)	C5'—C6'—C7'—C8'	−0.8 (4)
C2—C3—C4—C11	−0.7 (3)	C6'—C7'—C8'—C13'	−0.2 (3)
C12—C5—C6—C7	0.5 (3)	C7—C6—C9'—C13'	100.0 (2)
C12—C5—C6—C9'	179.39 (16)	C5—C6—C9'—C13'	−78.9 (2)
C5—C6—C7—C8	0.7 (3)	C7—C6—C9'—C10'	−141.21 (18)
C9'—C6—C7—C8	−178.28 (19)	C5—C6—C9'—C10'	39.9 (2)
C6—C7—C8—C13	−0.5 (3)	C2'—C1'—C10'—C11'	0.0 (3)
C2—C1—C10—C11	0.1 (3)	C2'—C1'—C10'—C9'	176.29 (18)
C2—C1—C10—C9	177.08 (18)	C13'—C9'—C10'—C1'	−176.25 (18)
C13—C9—C10—C1	−172.24 (18)	C6—C9'—C10'—C1'	58.8 (3)
C13—C9—C10—C11	4.98 (19)	C13'—C9'—C10'—C11'	0.32 (17)
C3—C4—C11—C10	1.7 (3)	C6—C9'—C10'—C11'	−124.61 (17)
C3—C4—C11—C12	−172.68 (18)	C3'—C4'—C11'—C10'	0.8 (3)
C1—C10—C11—C4	−1.4 (2)	C3'—C4'—C11'—C12'	−175.29 (19)
C9—C10—C11—C4	−178.95 (15)	C1'—C10'—C11'—C4'	−0.7 (3)
C1—C10—C11—C12	174.13 (15)	C9'—C10'—C11'—C4'	−177.67 (16)
C9—C10—C11—C12	−3.39 (18)	C1'—C10'—C11'—C12'	176.20 (17)
C6—C5—C12—C13	−1.7 (2)	C9'—C10'—C11'—C12'	−0.76 (18)
C6—C5—C12—C11	173.23 (16)	C6'—C5'—C12'—C13'	0.6 (3)
C4—C11—C12—C5	−0.3 (3)	C6'—C5'—C12'—C11'	176.7 (2)
C10—C11—C12—C5	−175.22 (17)	C4'—C11'—C12'—C5'	1.0 (3)
C4—C11—C12—C13	175.13 (17)	C10'—C11'—C12'—C5'	−175.45 (17)
C10—C11—C12—C13	0.20 (18)	C4'—C11'—C12'—C13'	177.41 (18)
C7—C8—C13—C12	−0.8 (3)	C10'—C11'—C12'—C13'	0.92 (18)
C7—C8—C13—C9	−177.28 (19)	C7'—C8'—C13'—C12'	1.5 (3)
C5—C12—C13—C8	1.9 (2)	C7'—C8'—C13'—C9'	−175.90 (19)
C11—C12—C13—C8	−174.10 (17)	C5'—C12'—C13'—C8'	−1.7 (3)
C5—C12—C13—C9	179.04 (16)	C11'—C12'—C13'—C8'	−178.54 (17)
C11—C12—C13—C9	3.06 (18)	C5'—C12'—C13'—C9'	176.14 (15)
C10—C9—C13—C8	171.96 (19)	C11'—C12'—C13'—C9'	−0.72 (18)
C10—C9—C13—C12	−4.86 (19)	C10'—C9'—C13'—C8'	177.84 (18)
C10'—C1'—C2'—C3'	0.6 (3)	C6—C9'—C13'—C8'	−55.1 (2)
C1'—C2'—C3'—C4'	−0.4 (4)	C10'—C9'—C13'—C12'	0.26 (17)
C2'—C3'—C4'—C11'	−0.3 (3)	C6—C9'—C13'—C12'	127.29 (16)