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organic compounds
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
In the title compound, C30H26, the dihedral angle between the two fluorene ring systems is 61.75 (4)°.
Experimental
Crystal data
|
Data collection: SMART (Bruker, 2001); cell 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
10.1107/S1600536808001517/xu2394sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808001517/xu2394Isup2.hkl
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
(silica gel) using n-hexane/dichloromethane as 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.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.
Data collection: SMART (Bruker, 2001); cell
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).C30H26 | F(000) = 1648 |
Mr = 386.51 | Dx = 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 |
Bruker SMART 1000 CCD area-detector diffractometer | 2859 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 27.4°, θmin = 3.1° |
ϕ and ω scans | h = −35→35 |
20365 measured reflections | k = −11→10 |
4970 independent reflections | l = −24→24 |
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(Fo2) + (0.0595P)2 + 0.3188P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
4970 reflections | Δρmax = 0.18 e Å−3 |
273 parameters | Δρmin = −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) |
C30H26 | V = 4372.7 (15) Å3 |
Mr = 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)° |
Bruker SMART 1000 CCD area-detector diffractometer | 2859 reflections with I > 2σ(I) |
20365 measured reflections | Rint = 0.031 |
4970 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.18 e Å−3 |
4970 reflections | Δρmin = −0.14 e Å−3 |
273 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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
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.
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.