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ISSN: 2056-9890

9-n-Butyl-9,9′-bi[9H-fluorene]

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[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.]); Murahashi & Moritani (1967[Murahashi, S. & Moritani, I. (1967). Tetrahedron, 23, 3631-3643.]).

[Scheme 1]

Experimental

Crystal data
  • C30H26

  • Mr = 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)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.122

  • S = 1.06

  • 4970 reflections

  • 273 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


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.

Refinement top

H atoms were positioned geometrically and treated as riding, with C—H = 0.93 (aromatic), 0.97 (methylene) or 0.96 Å (methyl), Uiso(H) = 1.5Ueq(C) for methyl or Uiso(H) = 1.2Ueq(C) for others.

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
[Figure 1] 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.
[Figure 2] Fig. 2. Partial packing view, H atoms are omitted for clarity.
9-n-Butyl-9,9'-bi[9H-fluorene] top
Crystal data top
C30H26F(000) = 1648
Mr = 386.51Dx = 1.174 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 12421 reflections
a = 27.164 (5) Åθ = 3.0–27.4°
b = 8.6369 (17) ŵ = 0.07 mm1
c = 19.232 (4) ÅT = 298 K
β = 104.28 (3)°Chunk, colorless
V = 4372.7 (15) Å30.46 × 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 tubeRint = 0.031
Graphite monochromatorθmax = 27.4°, θmin = 3.1°
ϕ and ω scansh = 3535
20365 measured reflectionsk = 1110
4970 independent reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0595P)2 + 0.3188P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
4970 reflectionsΔρmax = 0.18 e Å3
273 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0038 (4)
Crystal data top
C30H26V = 4372.7 (15) Å3
Mr = 386.51Z = 8
Monoclinic, C2/cMo Kα radiation
a = 27.164 (5) ŵ = 0.07 mm1
b = 8.6369 (17) ÅT = 298 K
c = 19.232 (4) Å0.46 × 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 reflectionsRint = 0.031
4970 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.06Δρmax = 0.18 e Å3
4970 reflectionsΔρmin = 0.14 e Å3
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
xyzUiso*/Ueq
C10.11948 (5)0.49033 (14)0.00529 (6)0.0446 (3)
C20.09626 (5)0.61937 (15)0.05656 (7)0.0482 (3)
C30.05151 (6)0.61827 (19)0.11011 (7)0.0622 (4)
H30.03220.52850.12030.075*
C40.03611 (7)0.7533 (2)0.14825 (8)0.0765 (5)
H40.00580.75470.18360.092*
C50.06533 (8)0.8858 (2)0.13425 (9)0.0788 (5)
H50.05460.97510.16070.095*
C60.11021 (7)0.88774 (17)0.08167 (9)0.0669 (4)
H60.12990.97700.07280.080*
C70.12544 (5)0.75404 (15)0.04213 (7)0.0501 (3)
C80.16888 (5)0.72391 (15)0.01911 (7)0.0492 (3)
C90.20847 (6)0.81905 (18)0.05433 (9)0.0648 (4)
H90.21090.92040.03920.078*
C100.24415 (6)0.7601 (2)0.11223 (9)0.0730 (5)
H100.27070.82270.13650.088*
C110.24097 (6)0.6098 (2)0.13449 (8)0.0679 (4)
H110.26530.57250.17370.082*
C120.20198 (5)0.51323 (17)0.09921 (7)0.0562 (4)
H120.20030.41130.11410.067*
C130.16563 (5)0.57100 (14)0.04155 (6)0.0453 (3)
C140.08081 (5)0.43871 (14)0.03910 (7)0.0481 (3)
H140.04980.40140.00550.058*
C150.06633 (5)0.56906 (16)0.08363 (7)0.0518 (3)
C160.04276 (5)0.71006 (18)0.06246 (9)0.0617 (4)
H160.03420.73840.01430.074*
C170.03222 (6)0.8079 (2)0.11398 (10)0.0757 (5)
H170.01670.90280.10020.091*
C180.04449 (7)0.7664 (2)0.18550 (10)0.0828 (5)
H180.03710.83370.21930.099*
C190.06752 (7)0.6270 (2)0.20742 (9)0.0744 (5)
H190.07550.59930.25560.089*
C200.07864 (5)0.52777 (18)0.15625 (7)0.0566 (4)
C210.09993 (5)0.37098 (17)0.16385 (7)0.0553 (4)
C220.11628 (6)0.2786 (2)0.22436 (8)0.0694 (4)
H220.11700.31760.26970.083*
C230.13134 (7)0.1289 (2)0.21644 (10)0.0774 (5)
H230.14290.06700.25670.093*
C240.12937 (7)0.07014 (19)0.14925 (10)0.0768 (5)
H240.13920.03170.14460.092*
C250.11283 (6)0.16108 (17)0.08828 (8)0.0661 (4)
H250.11090.11960.04300.079*
C260.09925 (5)0.31399 (16)0.09538 (7)0.0519 (3)
C270.13491 (5)0.35210 (15)0.04660 (7)0.0525 (3)
H27A0.15310.27730.01210.063*
H27B0.10430.30220.07420.063*
C280.16785 (6)0.39514 (15)0.09723 (7)0.0558 (4)
H28A0.15010.47210.13100.067*
H28B0.19900.44210.06950.067*
C290.18128 (7)0.26016 (17)0.13865 (8)0.0685 (4)
H29A0.15030.20820.16350.082*
H29B0.20140.18690.10520.082*
C300.21068 (8)0.3067 (2)0.19310 (9)0.0881 (6)
H30A0.19080.37830.22690.132*
H30B0.21770.21640.21810.132*
H30C0.24200.35500.16880.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0415 (7)0.0482 (7)0.0460 (7)0.0060 (6)0.0142 (5)0.0020 (6)
C20.0433 (7)0.0593 (8)0.0459 (7)0.0001 (6)0.0186 (6)0.0001 (6)
C30.0508 (9)0.0868 (11)0.0499 (8)0.0004 (8)0.0139 (7)0.0039 (8)
C40.0623 (11)0.1144 (15)0.0535 (9)0.0212 (10)0.0157 (8)0.0162 (10)
C50.0905 (14)0.0866 (12)0.0679 (10)0.0336 (11)0.0358 (10)0.0248 (10)
C60.0836 (12)0.0559 (8)0.0704 (10)0.0098 (8)0.0365 (9)0.0072 (8)
C70.0529 (8)0.0493 (8)0.0549 (8)0.0031 (6)0.0260 (6)0.0012 (6)
C80.0473 (8)0.0491 (7)0.0567 (8)0.0060 (6)0.0232 (6)0.0071 (6)
C90.0626 (10)0.0559 (8)0.0801 (10)0.0169 (7)0.0258 (8)0.0134 (8)
C100.0554 (10)0.0829 (12)0.0798 (11)0.0220 (8)0.0146 (9)0.0215 (9)
C110.0441 (9)0.0922 (12)0.0640 (9)0.0055 (8)0.0068 (7)0.0079 (9)
C120.0448 (8)0.0635 (8)0.0600 (8)0.0021 (7)0.0123 (6)0.0001 (7)
C130.0383 (7)0.0513 (7)0.0494 (7)0.0032 (6)0.0169 (6)0.0062 (6)
C140.0437 (7)0.0556 (7)0.0470 (7)0.0109 (6)0.0148 (6)0.0044 (6)
C150.0368 (7)0.0645 (8)0.0575 (8)0.0096 (6)0.0182 (6)0.0080 (7)
C160.0473 (8)0.0704 (9)0.0729 (9)0.0019 (7)0.0254 (7)0.0040 (8)
C170.0625 (11)0.0751 (11)0.0997 (13)0.0026 (8)0.0394 (9)0.0123 (10)
C180.0761 (12)0.0938 (13)0.0885 (13)0.0032 (10)0.0390 (10)0.0320 (11)
C190.0682 (11)0.0985 (13)0.0610 (9)0.0059 (10)0.0248 (8)0.0185 (9)
C200.0422 (8)0.0766 (10)0.0537 (8)0.0100 (7)0.0172 (6)0.0111 (7)
C210.0441 (8)0.0723 (9)0.0510 (8)0.0129 (7)0.0146 (6)0.0014 (7)
C220.0606 (10)0.0949 (12)0.0529 (8)0.0117 (9)0.0147 (7)0.0030 (9)
C230.0701 (11)0.0909 (12)0.0723 (11)0.0040 (9)0.0199 (9)0.0229 (10)
C240.0811 (12)0.0638 (10)0.0934 (13)0.0049 (9)0.0365 (10)0.0171 (10)
C250.0790 (11)0.0602 (9)0.0667 (9)0.0149 (8)0.0325 (8)0.0007 (8)
C260.0475 (8)0.0594 (8)0.0524 (8)0.0146 (6)0.0191 (6)0.0021 (7)
C270.0569 (9)0.0514 (7)0.0531 (7)0.0082 (6)0.0208 (6)0.0051 (6)
C280.0611 (9)0.0551 (8)0.0562 (8)0.0035 (7)0.0242 (7)0.0029 (7)
C290.0848 (12)0.0617 (9)0.0693 (10)0.0068 (8)0.0389 (9)0.0003 (8)
C300.1143 (16)0.0845 (12)0.0849 (12)0.0179 (11)0.0617 (11)0.0060 (10)
Geometric parameters (Å, º) top
C1—C21.5183 (18)C16—H160.9300
C1—C131.5203 (17)C17—C181.380 (2)
C1—C271.5481 (18)C17—H170.9300
C1—C141.5728 (18)C18—C191.374 (2)
C2—C31.386 (2)C18—H180.9300
C2—C71.3963 (18)C19—C201.393 (2)
C3—C41.386 (2)C19—H190.9300
C3—H30.9300C20—C211.466 (2)
C4—C51.381 (2)C21—C221.390 (2)
C4—H40.9300C21—C261.4018 (18)
C5—C61.379 (3)C22—C231.376 (2)
C5—H50.9300C22—H220.9300
C6—C71.3884 (19)C23—C241.377 (2)
C6—H60.9300C23—H230.9300
C7—C81.470 (2)C24—C251.391 (2)
C8—C91.3897 (19)C24—H240.9300
C8—C131.3989 (18)C25—C261.387 (2)
C9—C101.381 (2)C25—H250.9300
C9—H90.9300C27—C281.5222 (19)
C10—C111.376 (2)C27—H27A0.9700
C10—H100.9300C27—H27B0.9700
C11—C121.387 (2)C28—C291.5067 (19)
C11—H110.9300C28—H28A0.9700
C12—C131.3833 (19)C28—H28B0.9700
C12—H120.9300C29—C301.520 (2)
C14—C261.5217 (19)C29—H29A0.9700
C14—C151.5237 (18)C29—H29B0.9700
C14—H140.9800C30—H30A0.9600
C15—C161.389 (2)C30—H30B0.9600
C15—C201.3997 (19)C30—H30C0.9600
C16—C171.385 (2)
C2—C1—C13101.43 (10)C18—C17—C16120.85 (17)
C2—C1—C27110.77 (10)C18—C17—H17119.6
C13—C1—C27111.68 (11)C16—C17—H17119.6
C2—C1—C14109.53 (10)C19—C18—C17120.85 (16)
C13—C1—C14111.83 (10)C19—C18—H18119.6
C27—C1—C14111.19 (10)C17—C18—H18119.6
C3—C2—C7120.28 (13)C18—C19—C20118.94 (16)
C3—C2—C1128.70 (13)C18—C19—H19120.5
C7—C2—C1110.96 (11)C20—C19—H19120.5
C2—C3—C4118.83 (15)C19—C20—C15120.53 (15)
C2—C3—H3120.6C19—C20—C21130.31 (14)
C4—C3—H3120.6C15—C20—C21109.04 (12)
C5—C4—C3120.68 (16)C22—C21—C26120.82 (15)
C5—C4—H4119.7C22—C21—C20130.58 (14)
C3—C4—H4119.7C26—C21—C20108.50 (12)
C6—C5—C4120.98 (15)C23—C22—C21119.27 (15)
C6—C5—H5119.5C23—C22—H22120.4
C4—C5—H5119.5C21—C22—H22120.4
C5—C6—C7118.81 (16)C22—C23—C24120.43 (16)
C5—C6—H6120.6C22—C23—H23119.8
C7—C6—H6120.6C24—C23—H23119.8
C6—C7—C2120.40 (14)C23—C24—C25120.85 (17)
C6—C7—C8131.13 (13)C23—C24—H24119.6
C2—C7—C8108.42 (11)C25—C24—H24119.6
C9—C8—C13120.53 (13)C26—C25—C24119.55 (15)
C9—C8—C7131.11 (13)C26—C25—H25120.2
C13—C8—C7108.36 (11)C24—C25—H25120.2
C10—C9—C8118.67 (14)C25—C26—C21118.99 (13)
C10—C9—H9120.7C25—C26—C14130.76 (12)
C8—C9—H9120.7C21—C26—C14110.21 (12)
C11—C10—C9120.90 (14)C28—C27—C1114.59 (11)
C11—C10—H10119.5C28—C27—H27A108.6
C9—C10—H10119.5C1—C27—H27A108.6
C10—C11—C12120.93 (15)C28—C27—H27B108.6
C10—C11—H11119.5C1—C27—H27B108.6
C12—C11—H11119.5H27A—C27—H27B107.6
C13—C12—C11118.90 (14)C29—C28—C27113.98 (11)
C13—C12—H12120.6C29—C28—H28A108.8
C11—C12—H12120.6C27—C28—H28A108.8
C12—C13—C8120.06 (12)C29—C28—H28B108.8
C12—C13—C1129.12 (12)C27—C28—H28B108.8
C8—C13—C1110.82 (11)H28A—C28—H28B107.7
C26—C14—C15102.04 (10)C28—C29—C30113.36 (13)
C26—C14—C1116.10 (11)C28—C29—H29A108.9
C15—C14—C1113.28 (10)C30—C29—H29A108.9
C26—C14—H14108.3C28—C29—H29B108.9
C15—C14—H14108.3C30—C29—H29B108.9
C1—C14—H14108.3H29A—C29—H29B107.7
C16—C15—C20119.68 (13)C29—C30—H30A109.5
C16—C15—C14130.33 (13)C29—C30—H30B109.5
C20—C15—C14109.96 (12)H30A—C30—H30B109.5
C17—C16—C15119.15 (15)C29—C30—H30C109.5
C17—C16—H16120.4H30A—C30—H30C109.5
C15—C16—H16120.4H30B—C30—H30C109.5
C13—C1—C2—C3176.43 (13)C13—C1—C14—C1551.64 (14)
C27—C1—C2—C364.89 (18)C27—C1—C14—C15177.25 (11)
C14—C1—C2—C358.12 (17)C26—C14—C15—C16173.67 (13)
C13—C1—C2—C71.02 (13)C1—C14—C15—C1660.77 (18)
C27—C1—C2—C7117.65 (12)C26—C14—C15—C204.01 (14)
C14—C1—C2—C7119.34 (11)C1—C14—C15—C20121.55 (12)
C7—C2—C3—C40.8 (2)C20—C15—C16—C170.5 (2)
C1—C2—C3—C4176.49 (13)C14—C15—C16—C17177.98 (14)
C2—C3—C4—C51.4 (2)C15—C16—C17—C180.5 (2)
C3—C4—C5—C60.6 (3)C16—C17—C18—C190.0 (3)
C4—C5—C6—C70.7 (2)C17—C18—C19—C200.4 (3)
C5—C6—C7—C21.3 (2)C18—C19—C20—C150.3 (2)
C5—C6—C7—C8175.78 (14)C18—C19—C20—C21175.94 (15)
C3—C2—C7—C60.6 (2)C16—C15—C20—C190.1 (2)
C1—C2—C7—C6178.28 (12)C14—C15—C20—C19178.06 (13)
C3—C2—C7—C8177.11 (12)C16—C15—C20—C21176.36 (12)
C1—C2—C7—C80.59 (15)C14—C15—C20—C211.60 (15)
C6—C7—C8—C92.2 (3)C19—C20—C21—C221.9 (3)
C2—C7—C8—C9179.55 (14)C15—C20—C21—C22177.95 (15)
C6—C7—C8—C13177.20 (14)C19—C20—C21—C26174.22 (15)
C2—C7—C8—C130.16 (15)C15—C20—C21—C261.79 (15)
C13—C8—C9—C100.6 (2)C26—C21—C22—C230.8 (2)
C7—C8—C9—C10178.69 (14)C20—C21—C22—C23174.97 (15)
C8—C9—C10—C110.5 (2)C21—C22—C23—C241.2 (3)
C9—C10—C11—C120.3 (3)C22—C23—C24—C250.9 (3)
C10—C11—C12—C130.9 (2)C23—C24—C25—C261.5 (3)
C11—C12—C13—C80.8 (2)C24—C25—C26—C213.4 (2)
C11—C12—C13—C1179.59 (13)C24—C25—C26—C14179.11 (14)
C9—C8—C13—C120.0 (2)C22—C21—C26—C253.1 (2)
C7—C8—C13—C12179.46 (12)C20—C21—C26—C25173.51 (13)
C9—C8—C13—C1179.69 (12)C22—C21—C26—C14178.93 (13)
C7—C8—C13—C10.84 (14)C20—C21—C26—C144.46 (15)
C2—C1—C13—C12179.22 (13)C15—C14—C26—C25172.52 (14)
C27—C1—C13—C1262.77 (17)C1—C14—C26—C2563.80 (19)
C14—C1—C13—C1262.57 (17)C15—C14—C26—C215.13 (14)
C2—C1—C13—C81.12 (13)C1—C14—C26—C21118.54 (12)
C27—C1—C13—C8116.89 (12)C2—C1—C27—C2851.73 (15)
C14—C1—C13—C8117.77 (12)C13—C1—C27—C2860.53 (15)
C2—C1—C14—C26177.61 (10)C14—C1—C27—C28173.78 (11)
C13—C1—C14—C2665.98 (14)C1—C27—C28—C29178.29 (13)
C27—C1—C14—C2659.63 (14)C27—C28—C29—C30175.53 (14)
C2—C1—C14—C1559.99 (13)

Experimental details

Crystal data
Chemical formulaC30H26
Mr386.51
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)27.164 (5), 8.6369 (17), 19.232 (4)
β (°) 104.28 (3)
V3)4372.7 (15)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.46 × 0.38 × 0.35
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
20365, 4970, 2859
Rint0.031
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.122, 1.06
No. of reflections4970
No. of parameters273
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationMuller, 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
First citationMurahashi, S. & Moritani, I. (1967). Tetrahedron, 23, 3631–3643.  CrossRef CAS Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2008). publCIF. In preparation.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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