3,9′-Bi(9H-fluorene)

Liu, J.; Yu, W.

doi:10.1107/S1600536812024841

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2081

https://doi.org/10.1107/S1600536812024841

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3,9′-Bi(9H-fluorene)

Jie Liu ^a ^* and Wentao Yu ^a

^aState Key Laboratory of Crystal Materials, Shandong University, Shanda Nanlu 27 Jinan 250100, People's Republic of China
^*Correspondence e-mail: liujieicm@sdu.edu.cn

(Received 14 May 2012; accepted 31 May 2012; online 13 June 2012)

The title compound [systematic name: 9-(9H-fluoren-3-yl)-9H-fluorene], C₂₆H₁₈, was obtained unintentionally as the product of the synthesis of a compound based on fluorene–thiophene 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_r = 330.40
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.091
S = 1.04
2352 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812024841/zj2080sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024841/zj2080Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024841/zj2080Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024841/zj2080Isup4.cml

checkCIF report

Comment top

The molecule of the title complound (I) (Fig. 1) as the isomer of 9,9'-bi-9H-fluorene (9,9'-BF) is noncentrosymmetric, and the space group is P2₁2₁2₁. The two fluorene groups of the compound are like the letter 'T' in shape with a dihedral angle of 78.57 (6)°. Also, it is found that benzene rings of the fluorene units are not in the same plane, and the dihedral angles are 10.54 (6) and 5.84 (6)°, respectively. The crystal packing is stabilized by intermolecular C—-H···π interactions (Fig. 3).

Related literature top

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 top

The title compound, 3,9'-BF, was obtained unintentionally as the product of an attempted synthesis of 2,5-bis(9H-fluoren-9-yl)thiophene through Still reaction method. n-Butyllithium (20 ml, 2.5 M in hexane, 50 mmol) was added dropwise at -78 °C into a consistently stirred mixture of thiophene (22 mmol, 1.8 ml) and dry THF (80 ml), and the mixture would be with further stirring for 2 h at room temperature under an atmosphere of dry argon. After cooling the reaction mixture to -78 °C tri-n-butyltin chloride (15 ml) was added drop-wise to the mixture system. Then, the mixture was stirred continuously over one night before being poured into saturated NH₄Cl water solution (100 ml). After extraction with diethyl ether, the organic layer was dried over anhydrous MgSO₄ and the yellow fluid bis[tri-n-butyltin] thiophene (TBSB) was obtained. Furthermore, DMF (10 ml) was added to the mixture of TBSB (2.5 mmol, 1.654 g), 9-bromo-fluorene (6.25 mmol, 1.53 g) and potassium fluoride (2.5 mmol, 0.145 g) with stirring about 15 min. Appropriate amount of tetrakis (triphenylphosphine) palladium (0) was added to the stirring system and refluxed at 100 °C for 16 h under an atmosphere of dry argon. After extraction with dichloromethane (30 ml), the mixture was purified by silica-gel column chromatography to give 3,9'-BF, 9,9'-BF and 2,5-bis(9H-fluoren-9-yl)thiophene. Finally, single crystals of 3,9'-BF were obtained by recrystallizing from dichloromethane.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.
	Fig. 2. Part of the packing of the title compound, viewed down the a direction.
	Fig. 3. A view of the C—H ··· π interactions (dotted lines) in the crystal structure of the title compound.
	Fig. 4. Reaction scheme showing the formation of 3,9'-BF, 9,9'-BF and 2,5-bis(9H-fluoren-9-yl)thiophene (BFT).

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

Crystal data top

C₂₆H₁₈	F(000) = 696
M_r = 330.40	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0481P)² + 0.1328P] where P = (F_o² + 2F_c²)/3
2352 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₆H₁₈	V = 1753.20 (6) Å³
M_r = 330.40	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.22600 (1) Å	µ = 0.07 mm⁻¹
b = 8.3968 (2) Å	T = 293 K
c = 33.5357 (7) Å	0.45 × 0.22 × 0.16 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2352 independent reflections
Absorption correction: multi-scan (APEX2; Bruker,2005)	2014 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.989	R_int = 0.032
15454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.04	Δρ_max = 0.11 e Å⁻³
2352 reflections	Δρ_min = −0.14 e Å⁻³
235 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈
M_r	330.40
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.22600 (1), 8.3968 (2), 33.5357 (7)
V (Å³)	1753.20 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.45 × 0.22 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (APEX2; Bruker,2005)
T_min, T_max	0.969, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	15454, 2352, 2014
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.091, 1.04
No. of reflections	2352
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.14

Computer programs: APEX2 (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999) and Mercury (Macrae et al., 2006).

Acknowledgements

The authors gratefully acknowledge the National Natural Science Foundation of China (grant No. 51021062) and the 973 program of the People's Republic of China (grant No. 2010CB630702).

References

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