9-n-Butyl-9,9′-bi[9H-fluorene]

Yu, S.-Q.; Hu, B.-B.; Lu, P.

doi:10.1107/S1600536808001517

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o490

doi:10.1107/S1600536808001517

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9-n-Butyl-9,9′-bi[9H-fluorene]

Shu-Qiang Yu,^a Bin-Bin Hu ^a and Ping Lu ^a ^*

^aDepartment of Chemistry, Zhejiang University, Yuquan Campus, Hangzhou, 310027, People's Republic of China
^*Correspondence e-mail: pinglu@zju.edu.cn

(Received 16 December 2007; accepted 15 January 2008; online 23 January 2008)

In the title compound, C₃₀H₂₆, the dihedral angle between the two fluorene ring systems is 61.75 (4)°.

Related literature

For general background, see: Muller et al. (2003 ); Murahashi & Moritani (1967 ).

Experimental

Crystal data

C₃₀H₂₆
M_r = 386.51
Monoclinic, C 2/c
a = 27.164 (5) Å
b = 8.6369 (17) Å
c = 19.232 (4) Å
β = 104.28 (3)°
V = 4372.7 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 (2) K
0.46 × 0.38 × 0.35 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: none
20365 measured reflections
4970 independent reflections
2859 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.122
S = 1.06
4970 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001517/xu2394sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001517/xu2394Isup2.hkl

checkCIF report

Comment top

Fluorene derivatives, including polyfluorenes and oligofluorenes, remain a subject of intense investigation in recent years because they are very promising candidates for blue light-emitting materials in organic light-emitting devices (Muller et al., 2003). The title compound, 9-n-butyl-9,9'-bi(9H-fluorene)(hereinafter abbreviated to bbf), is one of bifluorene derivatives (Murahashi & Moritani, 1967).

The asymmetric unit of the title compound contains only one bbf molecule (Fig. 1). Two fluorene rings are linked together through their 9-position carbon atoms (C1 and C14). The dihedral angle between the two fluorene rings is 61.75 (4)°. The centroid to centroid distance between stacked fluorene rings is ca 5.92 Å, which is very long and prevents π-π stacking (Fig. 2). All bond lengths and angles are normal.

Related literature top

For general background, see: Muller et al. (2003); Murahashi & Moritani (1967).

Experimental top

All chemicals were of reagent grade quality obtained from commercial sources and used as received, unless stated otherwise. n-Butylithium (8 ml, 2.5 M, 20 mmol) was added to fluorene (1.66 g, 10 mmol) in 40 ml dry tetrahydrofuran under nitrogen at -78 °C. Subsequently, BF₃Et₂O (0.21 g, 2 mmol) was added. Kept it for 1 h, and warmed it to room temperature and stirred it overnight. After reaction completion, solvent was evaporated under reduced pressure. The crude products were purified by column chromatography (silica gel) using n-hexane/dichloromethane as eluent. The title compound was obtained as white solid in 30% yield. Colorless single crystals were grown from slow evaporation of a saturated CH₂Cl₂ solution of the compound.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).

Figures top

	Fig. 1. The molecular structure showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Partial packing view, H atoms are omitted for clarity.

9-n-Butyl-9,9'-bi[9H-fluorene] top

Crystal data top

C₃₀H₂₆	F(000) = 1648
M_r = 386.51	D_x = 1.174 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 12421 reflections
a = 27.164 (5) Å	θ = 3.0–27.4°
b = 8.6369 (17) Å	µ = 0.07 mm⁻¹
c = 19.232 (4) Å	T = 298 K
β = 104.28 (3)°	Chunk, colorless
V = 4372.7 (15) Å³	0.46 × 0.38 × 0.35 mm
Z = 8

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2859 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 27.4°, θ_min = 3.1°
ϕ and ω scans	h = −35→35
20365 measured reflections	k = −11→10
4970 independent reflections	l = −24→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0595P)² + 0.3188P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4970 reflections	Δρ_max = 0.18 e Å⁻³
273 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (4)

Crystal data top

C₃₀H₂₆	V = 4372.7 (15) Å³
M_r = 386.51	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.164 (5) Å	µ = 0.07 mm⁻¹
b = 8.6369 (17) Å	T = 298 K
c = 19.232 (4) Å	0.46 × 0.38 × 0.35 mm
β = 104.28 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2859 reflections with I > 2σ(I)
20365 measured reflections	R_int = 0.031
4970 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.06	Δρ_max = 0.18 e Å⁻³
4970 reflections	Δρ_min = −0.14 e Å⁻³
273 parameters

Special details top

Experimental. ¹H NMR (500 MHz, δ in p.p.m., CDCl₃): 0.68-0.74 (m, 5H), 0.17-1.22 (m, 2H), 2.55-2.58 (m, 2H), 4.58 (s, 1H), 6.76 (d, 2H, J = 7.00 Hz), 6.86 (d, 2H, J = 7.00 Hz), 6.97 (t, 2H, J = 7.50 Hz), 7.08 (t, 2H, J = 7.50 Hz), 7.17-7.23 (m, 4H), 7.49 (d, 2H, J = 7.50 Hz); ¹³C NMR (125 MHz, δ in p.p.m., CDCl₃): 14.15, 23.35, 26.45, 38.86, 55.48, 57.75, 119.39,119.62, 123.40, 125.84, 126.00, 126.90, 127.35, 141.59, 142.19, 144.37, 148.57; MS (EI): calcd for C₃₀H₂₆, 386.2; found, 386 (M⁺), 326, 313, 300, 221 (100), 179, 165, 152.

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	0.11948 (5)	0.49033 (14)	−0.00529 (6)	0.0446 (3)
C2	0.09626 (5)	0.61937 (15)	−0.05656 (7)	0.0482 (3)
C3	0.05151 (6)	0.61827 (19)	−0.11011 (7)	0.0622 (4)
H3	0.0322	0.5285	−0.1203	0.075*
C4	0.03611 (7)	0.7533 (2)	−0.14825 (8)	0.0765 (5)
H4	0.0058	0.7547	−0.1836	0.092*
C5	0.06533 (8)	0.8858 (2)	−0.13425 (9)	0.0788 (5)
H5	0.0546	0.9751	−0.1607	0.095*
C6	0.11021 (7)	0.88774 (17)	−0.08167 (9)	0.0669 (4)
H6	0.1299	0.9770	−0.0728	0.080*
C7	0.12544 (5)	0.75404 (15)	−0.04213 (7)	0.0501 (3)
C8	0.16888 (5)	0.72391 (15)	0.01911 (7)	0.0492 (3)
C9	0.20847 (6)	0.81905 (18)	0.05433 (9)	0.0648 (4)
H9	0.2109	0.9204	0.0392	0.078*
C10	0.24415 (6)	0.7601 (2)	0.11223 (9)	0.0730 (5)
H10	0.2707	0.8227	0.1365	0.088*
C11	0.24097 (6)	0.6098 (2)	0.13449 (8)	0.0679 (4)
H11	0.2653	0.5725	0.1737	0.082*
C12	0.20198 (5)	0.51323 (17)	0.09921 (7)	0.0562 (4)
H12	0.2003	0.4113	0.1141	0.067*
C13	0.16563 (5)	0.57100 (14)	0.04155 (6)	0.0453 (3)
C14	0.08081 (5)	0.43871 (14)	0.03910 (7)	0.0481 (3)
H14	0.0498	0.4014	0.0055	0.058*
C15	0.06633 (5)	0.56906 (16)	0.08363 (7)	0.0518 (3)
C16	0.04276 (5)	0.71006 (18)	0.06246 (9)	0.0617 (4)
H16	0.0342	0.7384	0.0143	0.074*
C17	0.03222 (6)	0.8079 (2)	0.11398 (10)	0.0757 (5)
H17	0.0167	0.9028	0.1002	0.091*
C18	0.04449 (7)	0.7664 (2)	0.18550 (10)	0.0828 (5)
H18	0.0371	0.8337	0.2193	0.099*
C19	0.06752 (7)	0.6270 (2)	0.20742 (9)	0.0744 (5)
H19	0.0755	0.5993	0.2556	0.089*
C20	0.07864 (5)	0.52777 (18)	0.15625 (7)	0.0566 (4)
C21	0.09993 (5)	0.37098 (17)	0.16385 (7)	0.0553 (4)
C22	0.11628 (6)	0.2786 (2)	0.22436 (8)	0.0694 (4)
H22	0.1170	0.3176	0.2697	0.083*
C23	0.13134 (7)	0.1289 (2)	0.21644 (10)	0.0774 (5)
H23	0.1429	0.0670	0.2567	0.093*
C24	0.12937 (7)	0.07014 (19)	0.14925 (10)	0.0768 (5)
H24	0.1392	−0.0317	0.1446	0.092*
C25	0.11283 (6)	0.16108 (17)	0.08828 (8)	0.0661 (4)
H25	0.1109	0.1196	0.0430	0.079*
C26	0.09925 (5)	0.31399 (16)	0.09538 (7)	0.0519 (3)
C27	0.13491 (5)	0.35210 (15)	−0.04660 (7)	0.0525 (3)
H27A	0.1531	0.2773	−0.0121	0.063*
H27B	0.1043	0.3022	−0.0742	0.063*
C28	0.16785 (6)	0.39514 (15)	−0.09723 (7)	0.0558 (4)
H28A	0.1501	0.4721	−0.1310	0.067*
H28B	0.1990	0.4421	−0.0695	0.067*
C29	0.18128 (7)	0.26016 (17)	−0.13865 (8)	0.0685 (4)
H29A	0.1503	0.2082	−0.1635	0.082*
H29B	0.2014	0.1869	−0.1052	0.082*
C30	0.21068 (8)	0.3067 (2)	−0.19310 (9)	0.0881 (6)
H30A	0.1908	0.3783	−0.2269	0.132*
H30B	0.2177	0.2164	−0.2181	0.132*
H30C	0.2420	0.3550	−0.1688	0.132*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0415 (7)	0.0482 (7)	0.0460 (7)	−0.0060 (6)	0.0142 (5)	−0.0020 (6)
C2	0.0433 (7)	0.0593 (8)	0.0459 (7)	−0.0001 (6)	0.0186 (6)	0.0001 (6)
C3	0.0508 (9)	0.0868 (11)	0.0499 (8)	0.0004 (8)	0.0139 (7)	0.0039 (8)
C4	0.0623 (11)	0.1144 (15)	0.0535 (9)	0.0212 (10)	0.0157 (8)	0.0162 (10)
C5	0.0905 (14)	0.0866 (12)	0.0679 (10)	0.0336 (11)	0.0358 (10)	0.0248 (10)
C6	0.0836 (12)	0.0559 (8)	0.0704 (10)	0.0098 (8)	0.0365 (9)	0.0072 (8)
C7	0.0529 (8)	0.0493 (8)	0.0549 (8)	0.0031 (6)	0.0260 (6)	0.0012 (6)
C8	0.0473 (8)	0.0491 (7)	0.0567 (8)	−0.0060 (6)	0.0232 (6)	−0.0071 (6)
C9	0.0626 (10)	0.0559 (8)	0.0801 (10)	−0.0169 (7)	0.0258 (8)	−0.0134 (8)
C10	0.0554 (10)	0.0829 (12)	0.0798 (11)	−0.0220 (8)	0.0146 (9)	−0.0215 (9)
C11	0.0441 (9)	0.0922 (12)	0.0640 (9)	−0.0055 (8)	0.0068 (7)	−0.0079 (9)
C12	0.0448 (8)	0.0635 (8)	0.0600 (8)	−0.0021 (7)	0.0123 (6)	0.0001 (7)
C13	0.0383 (7)	0.0513 (7)	0.0494 (7)	−0.0032 (6)	0.0169 (6)	−0.0062 (6)
C14	0.0437 (7)	0.0556 (7)	0.0470 (7)	−0.0109 (6)	0.0148 (6)	−0.0044 (6)
C15	0.0368 (7)	0.0645 (8)	0.0575 (8)	−0.0096 (6)	0.0182 (6)	−0.0080 (7)
C16	0.0473 (8)	0.0704 (9)	0.0729 (9)	−0.0019 (7)	0.0254 (7)	−0.0040 (8)
C17	0.0625 (11)	0.0751 (11)	0.0997 (13)	0.0026 (8)	0.0394 (9)	−0.0123 (10)
C18	0.0761 (12)	0.0938 (13)	0.0885 (13)	−0.0032 (10)	0.0390 (10)	−0.0320 (11)
C19	0.0682 (11)	0.0985 (13)	0.0610 (9)	−0.0059 (10)	0.0248 (8)	−0.0185 (9)
C20	0.0422 (8)	0.0766 (10)	0.0537 (8)	−0.0100 (7)	0.0172 (6)	−0.0111 (7)
C21	0.0441 (8)	0.0723 (9)	0.0510 (8)	−0.0129 (7)	0.0146 (6)	−0.0014 (7)
C22	0.0606 (10)	0.0949 (12)	0.0529 (8)	−0.0117 (9)	0.0147 (7)	0.0030 (9)
C23	0.0701 (11)	0.0909 (12)	0.0723 (11)	−0.0040 (9)	0.0199 (9)	0.0229 (10)
C24	0.0811 (12)	0.0638 (10)	0.0934 (13)	−0.0049 (9)	0.0365 (10)	0.0171 (10)
C25	0.0790 (11)	0.0602 (9)	0.0667 (9)	−0.0149 (8)	0.0325 (8)	0.0007 (8)
C26	0.0475 (8)	0.0594 (8)	0.0524 (8)	−0.0146 (6)	0.0191 (6)	−0.0021 (7)
C27	0.0569 (9)	0.0514 (7)	0.0531 (7)	−0.0082 (6)	0.0208 (6)	−0.0051 (6)
C28	0.0611 (9)	0.0551 (8)	0.0562 (8)	−0.0035 (7)	0.0242 (7)	−0.0029 (7)
C29	0.0848 (12)	0.0617 (9)	0.0693 (10)	0.0068 (8)	0.0389 (9)	−0.0003 (8)
C30	0.1143 (16)	0.0845 (12)	0.0849 (12)	0.0179 (11)	0.0617 (11)	0.0060 (10)

Geometric parameters (Å, º) top

C1—C2	1.5183 (18)	C16—H16	0.9300
C1—C13	1.5203 (17)	C17—C18	1.380 (2)
C1—C27	1.5481 (18)	C17—H17	0.9300
C1—C14	1.5728 (18)	C18—C19	1.374 (2)
C2—C3	1.386 (2)	C18—H18	0.9300
C2—C7	1.3963 (18)	C19—C20	1.393 (2)
C3—C4	1.386 (2)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.466 (2)
C4—C5	1.381 (2)	C21—C22	1.390 (2)
C4—H4	0.9300	C21—C26	1.4018 (18)
C5—C6	1.379 (3)	C22—C23	1.376 (2)
C5—H5	0.9300	C22—H22	0.9300
C6—C7	1.3884 (19)	C23—C24	1.377 (2)
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.470 (2)	C24—C25	1.391 (2)
C8—C9	1.3897 (19)	C24—H24	0.9300
C8—C13	1.3989 (18)	C25—C26	1.387 (2)
C9—C10	1.381 (2)	C25—H25	0.9300
C9—H9	0.9300	C27—C28	1.5222 (19)
C10—C11	1.376 (2)	C27—H27A	0.9700
C10—H10	0.9300	C27—H27B	0.9700
C11—C12	1.387 (2)	C28—C29	1.5067 (19)
C11—H11	0.9300	C28—H28A	0.9700
C12—C13	1.3833 (19)	C28—H28B	0.9700
C12—H12	0.9300	C29—C30	1.520 (2)
C14—C26	1.5217 (19)	C29—H29A	0.9700
C14—C15	1.5237 (18)	C29—H29B	0.9700
C14—H14	0.9800	C30—H30A	0.9600
C15—C16	1.389 (2)	C30—H30B	0.9600
C15—C20	1.3997 (19)	C30—H30C	0.9600
C16—C17	1.385 (2)

C2—C1—C13	101.43 (10)	C18—C17—C16	120.85 (17)
C2—C1—C27	110.77 (10)	C18—C17—H17	119.6
C13—C1—C27	111.68 (11)	C16—C17—H17	119.6
C2—C1—C14	109.53 (10)	C19—C18—C17	120.85 (16)
C13—C1—C14	111.83 (10)	C19—C18—H18	119.6
C27—C1—C14	111.19 (10)	C17—C18—H18	119.6
C3—C2—C7	120.28 (13)	C18—C19—C20	118.94 (16)
C3—C2—C1	128.70 (13)	C18—C19—H19	120.5
C7—C2—C1	110.96 (11)	C20—C19—H19	120.5
C2—C3—C4	118.83 (15)	C19—C20—C15	120.53 (15)
C2—C3—H3	120.6	C19—C20—C21	130.31 (14)
C4—C3—H3	120.6	C15—C20—C21	109.04 (12)
C5—C4—C3	120.68 (16)	C22—C21—C26	120.82 (15)
C5—C4—H4	119.7	C22—C21—C20	130.58 (14)
C3—C4—H4	119.7	C26—C21—C20	108.50 (12)
C6—C5—C4	120.98 (15)	C23—C22—C21	119.27 (15)
C6—C5—H5	119.5	C23—C22—H22	120.4
C4—C5—H5	119.5	C21—C22—H22	120.4
C5—C6—C7	118.81 (16)	C22—C23—C24	120.43 (16)
C5—C6—H6	120.6	C22—C23—H23	119.8
C7—C6—H6	120.6	C24—C23—H23	119.8
C6—C7—C2	120.40 (14)	C23—C24—C25	120.85 (17)
C6—C7—C8	131.13 (13)	C23—C24—H24	119.6
C2—C7—C8	108.42 (11)	C25—C24—H24	119.6
C9—C8—C13	120.53 (13)	C26—C25—C24	119.55 (15)
C9—C8—C7	131.11 (13)	C26—C25—H25	120.2
C13—C8—C7	108.36 (11)	C24—C25—H25	120.2
C10—C9—C8	118.67 (14)	C25—C26—C21	118.99 (13)
C10—C9—H9	120.7	C25—C26—C14	130.76 (12)
C8—C9—H9	120.7	C21—C26—C14	110.21 (12)
C11—C10—C9	120.90 (14)	C28—C27—C1	114.59 (11)
C11—C10—H10	119.5	C28—C27—H27A	108.6
C9—C10—H10	119.5	C1—C27—H27A	108.6
C10—C11—C12	120.93 (15)	C28—C27—H27B	108.6
C10—C11—H11	119.5	C1—C27—H27B	108.6
C12—C11—H11	119.5	H27A—C27—H27B	107.6
C13—C12—C11	118.90 (14)	C29—C28—C27	113.98 (11)
C13—C12—H12	120.6	C29—C28—H28A	108.8
C11—C12—H12	120.6	C27—C28—H28A	108.8
C12—C13—C8	120.06 (12)	C29—C28—H28B	108.8
C12—C13—C1	129.12 (12)	C27—C28—H28B	108.8
C8—C13—C1	110.82 (11)	H28A—C28—H28B	107.7
C26—C14—C15	102.04 (10)	C28—C29—C30	113.36 (13)
C26—C14—C1	116.10 (11)	C28—C29—H29A	108.9
C15—C14—C1	113.28 (10)	C30—C29—H29A	108.9
C26—C14—H14	108.3	C28—C29—H29B	108.9
C15—C14—H14	108.3	C30—C29—H29B	108.9
C1—C14—H14	108.3	H29A—C29—H29B	107.7
C16—C15—C20	119.68 (13)	C29—C30—H30A	109.5
C16—C15—C14	130.33 (13)	C29—C30—H30B	109.5
C20—C15—C14	109.96 (12)	H30A—C30—H30B	109.5
C17—C16—C15	119.15 (15)	C29—C30—H30C	109.5
C17—C16—H16	120.4	H30A—C30—H30C	109.5
C15—C16—H16	120.4	H30B—C30—H30C	109.5

C13—C1—C2—C3	−176.43 (13)	C13—C1—C14—C15	51.64 (14)
C27—C1—C2—C3	64.89 (18)	C27—C1—C14—C15	177.25 (11)
C14—C1—C2—C3	−58.12 (17)	C26—C14—C15—C16	−173.67 (13)
C13—C1—C2—C7	1.02 (13)	C1—C14—C15—C16	60.77 (18)
C27—C1—C2—C7	−117.65 (12)	C26—C14—C15—C20	4.01 (14)
C14—C1—C2—C7	119.34 (11)	C1—C14—C15—C20	−121.55 (12)
C7—C2—C3—C4	−0.8 (2)	C20—C15—C16—C17	0.5 (2)
C1—C2—C3—C4	176.49 (13)	C14—C15—C16—C17	177.98 (14)
C2—C3—C4—C5	1.4 (2)	C15—C16—C17—C18	−0.5 (2)
C3—C4—C5—C6	−0.6 (3)	C16—C17—C18—C19	0.0 (3)
C4—C5—C6—C7	−0.7 (2)	C17—C18—C19—C20	0.4 (3)
C5—C6—C7—C2	1.3 (2)	C18—C19—C20—C15	−0.3 (2)
C5—C6—C7—C8	−175.78 (14)	C18—C19—C20—C21	−175.94 (15)
C3—C2—C7—C6	−0.6 (2)	C16—C15—C20—C19	−0.1 (2)
C1—C2—C7—C6	−178.28 (12)	C14—C15—C20—C19	−178.06 (13)
C3—C2—C7—C8	177.11 (12)	C16—C15—C20—C21	176.36 (12)
C1—C2—C7—C8	−0.59 (15)	C14—C15—C20—C21	−1.60 (15)
C6—C7—C8—C9	−2.2 (3)	C19—C20—C21—C22	−1.9 (3)
C2—C7—C8—C9	−179.55 (14)	C15—C20—C21—C22	−177.95 (15)
C6—C7—C8—C13	177.20 (14)	C19—C20—C21—C26	174.22 (15)
C2—C7—C8—C13	−0.16 (15)	C15—C20—C21—C26	−1.79 (15)
C13—C8—C9—C10	−0.6 (2)	C26—C21—C22—C23	−0.8 (2)
C7—C8—C9—C10	178.69 (14)	C20—C21—C22—C23	174.97 (15)
C8—C9—C10—C11	0.5 (2)	C21—C22—C23—C24	−1.2 (3)
C9—C10—C11—C12	0.3 (3)	C22—C23—C24—C25	0.9 (3)
C10—C11—C12—C13	−0.9 (2)	C23—C24—C25—C26	1.5 (3)
C11—C12—C13—C8	0.8 (2)	C24—C25—C26—C21	−3.4 (2)
C11—C12—C13—C1	−179.59 (13)	C24—C25—C26—C14	179.11 (14)
C9—C8—C13—C12	0.0 (2)	C22—C21—C26—C25	3.1 (2)
C7—C8—C13—C12	−179.46 (12)	C20—C21—C26—C25	−173.51 (13)
C9—C8—C13—C1	−179.69 (12)	C22—C21—C26—C14	−178.93 (13)
C7—C8—C13—C1	0.84 (14)	C20—C21—C26—C14	4.46 (15)
C2—C1—C13—C12	179.22 (13)	C15—C14—C26—C25	172.52 (14)
C27—C1—C13—C12	−62.77 (17)	C1—C14—C26—C25	−63.80 (19)
C14—C1—C13—C12	62.57 (17)	C15—C14—C26—C21	−5.13 (14)
C2—C1—C13—C8	−1.12 (13)	C1—C14—C26—C21	118.54 (12)
C27—C1—C13—C8	116.89 (12)	C2—C1—C27—C28	51.73 (15)
C14—C1—C13—C8	−117.77 (12)	C13—C1—C27—C28	−60.53 (15)
C2—C1—C14—C26	−177.61 (10)	C14—C1—C27—C28	173.78 (11)
C13—C1—C14—C26	−65.98 (14)	C1—C27—C28—C29	−178.29 (13)
C27—C1—C14—C26	59.63 (14)	C27—C28—C29—C30	175.53 (14)
C2—C1—C14—C15	−59.99 (13)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₆
M_r	386.51
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	27.164 (5), 8.6369 (17), 19.232 (4)
β (°)	104.28 (3)
V (Å³)	4372.7 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.46 × 0.38 × 0.35

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20365, 4970, 2859
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.122, 1.06
No. of reflections	4970
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).

Acknowledgements

The authors thank the National Natural Science Foundation of China (20674070) and the Natural Science Foundation of Zhejiang Province (R404109).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Muller, C. D., Falcou, A., Reckefuss, N., Rojahn, M., Wiederhirn, V., Rudati, P., Frohne, H., Nuyken, O., Becker, H. & Meerholz, K. (2003). Nature (London), 421, 829–833. Web of Science CrossRef PubMed Google Scholar
Murahashi, S. & Moritani, I. (1967). Tetrahedron, 23, 3631–3643. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar