organic compounds
2,2′-Bi(9,9-diethylfluorene)
aResearch Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea, and bDivision of Science Education, Kangwon National University, Chuncheon 200-701, Republic of Korea
*Correspondence e-mail: kangy@kangwon.ac.kr
The title compound, C34H34, 9,9,9′,9′-tetraethyl-2,2′-bi(9H-fluorene), crystallized with two crystallographically independent molecules (A and B) in the These differ mainly in the orientation of the lateral ethyl chains: in molecule A, they are both on the same side of the molecule whereas in molecule B, one diethylfluorene moiety has undergone a 180° rotation such that the two pairs of ethyl residues appear on opposite sides of the molecule. The fluorene ring systems subtend dihedral angles of 31.37 (4) and 43.18 (3)° in molecules A and B, respectively. Hence the two fluorene moieties are tilted slightly toward one another. This may be due to the presence of intermolecular C—H⋯π interactions between neighboring molecules. The lateral ethyl chains (excluding H atoms) are also almost planar, with each pair almost perpendicular to the plane of the fluorene system to which they are attached with dihedral angles between the ethyl and fluorene planes in the range 86.04 (8)–89.5 (1)°.
CCDC reference: 982343
Related literature
For details of conductive small molecules and their applications in organic electronics, see: Chao et al. (2005); Gong & Lagowski (2008); Hapiot et al. (2005). For details of the synthesis of the title compound, see: Hapiot et al. (2005). For the crystal structures of other fluorene derivatives, see: Han et al. (2006); Jasinski et al. (2003); Suchod et al. (2000).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 982343
10.1107/S1600536814001378/sj5384sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001378/sj5384Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001378/sj5384Isup3.cml
The title compound was synthesized by a literature method (Hapiot et al., 2005). Slow evaporation of a solution of the title compound in dichloromethane and hexane (1:2 v/v) gave single crystals suitable for X-ray analysis.
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for methylene, and d(C—H) = 0.98 Å, Uiso = 1.2Ueq(C) for methyl protons.
As a potential conductive small molecule, 2,2'-bi(9,9-diethylfluorene) is regarded as one of the most promising candidate materials for organic electronics due to its unique photophysical properties, good thermal stability as well as a stable glass phase at room temperature (Chao et al., 2005; Hapiot et al., 2005). Therefore, the
of 2,2'-bi(9,9-diethylfluorene) plays key role in understanding the reasons that this compound has a high thermal stability and a stable glass form (Gong & Lagowski, 2008).The title compound (Scheme 1, Fig.1) crystallized with two crystallographically independent molecules (A and B) in the π-conjugation of two fluorene segments may be caused by intermolecular intermolecular C—H···π interactions between neighboring molecules (Table 1). All bond lengths and bond angles are normal and comparable to those of observed in the structures of other fluorene derivatives (Han et al., 2006; Jasinski et al., 2003; Suchod et al., 2000).
which differ mainly in the orientation of the lateral ethyl chains in each molecule. The ethyl substituents in A are found on the same side of the molecule whereas in molecule B one diethylfluorene moiety has undergone a 180° rotation such that the two pairs of ethyl residues appear on opposite sides of the molecule. In both molecules the fluorene segments are planar with a maximum r.m.s. deviation of 0.048 ° for the C48–C60 ring system. The ethyl chains (excluding H atoms) are also planar, with each pair almost perpendicular to the plane of the fluorene system to which they are attached, with dihedral angles between the ethyl and fluorene planes in the range 86.04 (8)° to 89.5 (1)°. This interruption ofFor details of conductive small molecules and their applications in organic electronics, see: Chao et al. (2005); Gong & Lagowski (2008); Hapiot et al. (2005). For details of the synthesis of the title compound, see: Hapiot et al. (2005). For the crystal structures of other fluorene derivatives, see: Han et al. (2006); Jasinski et al. (2003); Suchod et al. (2000).
Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity. |
C34H34 | Z = 4 |
Mr = 442.61 | F(000) = 952 |
Triclinic, P1 | Dx = 1.132 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.3149 (6) Å | Cell parameters from 6198 reflections |
b = 14.8415 (7) Å | θ = 2.3–28.3° |
c = 15.8795 (8) Å | µ = 0.06 mm−1 |
α = 69.725 (1)° | T = 173 K |
β = 89.368 (1)° | Block, colourless |
γ = 73.433 (1)° | 0.40 × 0.35 × 0.25 mm |
V = 2597.0 (2) Å3 |
Bruker APEXII CCD area detector diffractometer | 10001 independent reflections |
Radiation source: fine-focus sealed tube | 7320 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 26.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→15 |
Tmin = 0.975, Tmax = 0.984 | k = −18→18 |
14768 measured reflections | l = −19→14 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0373P)2 + 1.6362P] where P = (Fo2 + 2Fc2)/3 |
10001 reflections | (Δ/σ)max < 0.001 |
613 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C34H34 | γ = 73.433 (1)° |
Mr = 442.61 | V = 2597.0 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 12.3149 (6) Å | Mo Kα radiation |
b = 14.8415 (7) Å | µ = 0.06 mm−1 |
c = 15.8795 (8) Å | T = 173 K |
α = 69.725 (1)° | 0.40 × 0.35 × 0.25 mm |
β = 89.368 (1)° |
Bruker APEXII CCD area detector diffractometer | 10001 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 7320 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.984 | Rint = 0.032 |
14768 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.27 e Å−3 |
10001 reflections | Δρmin = −0.26 e Å−3 |
613 parameters |
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 | 0.34960 (19) | 0.12638 (16) | 0.07528 (15) | 0.0320 (5) | |
C2 | 0.33666 (18) | 0.21742 (16) | −0.01130 (15) | 0.0315 (5) | |
C3 | 0.3600 (2) | 0.21887 (18) | −0.09731 (16) | 0.0408 (6) | |
H3 | 0.3901 | 0.1578 | −0.1081 | 0.049* | |
C4 | 0.3385 (2) | 0.31178 (19) | −0.16778 (16) | 0.0425 (6) | |
H4 | 0.3540 | 0.3138 | −0.2270 | 0.051* | |
C5 | 0.2948 (2) | 0.40117 (17) | −0.15222 (16) | 0.0366 (5) | |
H5 | 0.2801 | 0.4637 | −0.2010 | 0.044* | |
C6 | 0.27234 (18) | 0.39989 (16) | −0.06604 (15) | 0.0303 (5) | |
H6 | 0.2427 | 0.4610 | −0.0553 | 0.036* | |
C7 | 0.29396 (16) | 0.30763 (16) | 0.00414 (14) | 0.0266 (5) | |
C8 | 0.27622 (16) | 0.28309 (15) | 0.10035 (14) | 0.0254 (4) | |
C9 | 0.23575 (17) | 0.34442 (15) | 0.14993 (14) | 0.0273 (5) | |
H9 | 0.2155 | 0.4156 | 0.1219 | 0.033* | |
C10 | 0.22538 (17) | 0.30043 (15) | 0.24073 (14) | 0.0271 (5) | |
H10 | 0.1978 | 0.3424 | 0.2747 | 0.033* | |
C11 | 0.25446 (16) | 0.19547 (15) | 0.28429 (14) | 0.0247 (4) | |
C12 | 0.29613 (17) | 0.13462 (15) | 0.23337 (14) | 0.0273 (5) | |
H12 | 0.3170 | 0.0634 | 0.2612 | 0.033* | |
C13 | 0.30680 (17) | 0.17834 (15) | 0.14255 (14) | 0.0267 (5) | |
C14 | 0.23690 (16) | 0.15167 (15) | 0.38076 (14) | 0.0245 (4) | |
C15 | 0.24091 (16) | 0.20295 (15) | 0.43988 (14) | 0.0258 (5) | |
H15 | 0.2596 | 0.2644 | 0.4188 | 0.031* | |
C16 | 0.21796 (17) | 0.16465 (15) | 0.52783 (14) | 0.0260 (5) | |
C17 | 0.22179 (18) | 0.20635 (17) | 0.60234 (15) | 0.0310 (5) | |
C18 | 0.17970 (18) | 0.13300 (17) | 0.67919 (15) | 0.0320 (5) | |
C19 | 0.1576 (2) | 0.13455 (19) | 0.76502 (16) | 0.0400 (6) | |
H19 | 0.1666 | 0.1875 | 0.7822 | 0.048* | |
C20 | 0.1221 (2) | 0.0573 (2) | 0.82521 (17) | 0.0438 (6) | |
H20 | 0.1059 | 0.0581 | 0.8836 | 0.053* | |
C21 | 0.1101 (2) | −0.02093 (19) | 0.80109 (17) | 0.0419 (6) | |
H21 | 0.0866 | −0.0734 | 0.8433 | 0.050* | |
C22 | 0.13196 (19) | −0.02323 (17) | 0.71561 (15) | 0.0350 (5) | |
H22 | 0.1238 | −0.0768 | 0.6990 | 0.042* | |
C23 | 0.16601 (17) | 0.05458 (16) | 0.65500 (14) | 0.0283 (5) | |
C24 | 0.19018 (16) | 0.07423 (15) | 0.56038 (14) | 0.0258 (5) | |
C25 | 0.18838 (18) | 0.02103 (15) | 0.50411 (15) | 0.0293 (5) | |
H25 | 0.1714 | −0.0411 | 0.5260 | 0.035* | |
C26 | 0.21181 (17) | 0.05987 (16) | 0.41523 (15) | 0.0289 (5) | |
H26 | 0.2108 | 0.0233 | 0.3767 | 0.035* | |
C27 | 0.4756 (2) | 0.06177 (19) | 0.10259 (17) | 0.0448 (7) | |
H27A | 0.4794 | 0.0018 | 0.1567 | 0.054* | |
H27B | 0.5042 | 0.0378 | 0.0532 | 0.054* | |
C28 | 0.5540 (2) | 0.1161 (2) | 0.1227 (2) | 0.0598 (8) | |
H28A | 0.6317 | 0.0701 | 0.1395 | 0.072* | |
H28B | 0.5279 | 0.1386 | 0.1727 | 0.072* | |
H28C | 0.5528 | 0.1745 | 0.0690 | 0.072* | |
C29 | 0.2755 (2) | 0.06115 (17) | 0.06740 (17) | 0.0404 (6) | |
H29A | 0.3030 | 0.0325 | 0.0206 | 0.048* | |
H29B | 0.2858 | 0.0043 | 0.1255 | 0.048* | |
C30 | 0.1493 (2) | 0.11732 (19) | 0.04379 (19) | 0.0481 (7) | |
H30A | 0.1081 | 0.0709 | 0.0403 | 0.058* | |
H30B | 0.1377 | 0.1725 | −0.0146 | 0.058* | |
H30C | 0.1206 | 0.1448 | 0.0904 | 0.058* | |
C31 | 0.3473 (2) | 0.1978 (2) | 0.62692 (17) | 0.0421 (6) | |
H31A | 0.3711 | 0.2480 | 0.5769 | 0.051* | |
H31B | 0.3503 | 0.2157 | 0.6812 | 0.051* | |
C32 | 0.4327 (2) | 0.0948 (2) | 0.64500 (18) | 0.0504 (7) | |
H32A | 0.5088 | 0.0964 | 0.6602 | 0.061* | |
H32B | 0.4328 | 0.0770 | 0.5910 | 0.061* | |
H32C | 0.4114 | 0.0445 | 0.6955 | 0.061* | |
C33 | 0.1486 (2) | 0.31692 (17) | 0.57677 (16) | 0.0378 (6) | |
H33A | 0.1510 | 0.3369 | 0.6299 | 0.045* | |
H33B | 0.1830 | 0.3596 | 0.5284 | 0.045* | |
C34 | 0.0246 (2) | 0.33856 (18) | 0.54482 (18) | 0.0443 (6) | |
H34A | −0.0153 | 0.4103 | 0.5299 | 0.053* | |
H34B | −0.0114 | 0.2985 | 0.5928 | 0.053* | |
H34C | 0.0207 | 0.3208 | 0.4912 | 0.053* | |
C35 | 0.38207 (18) | −0.33106 (17) | 0.59294 (15) | 0.0321 (5) | |
C36 | 0.33463 (18) | −0.27599 (17) | 0.49421 (15) | 0.0311 (5) | |
C37 | 0.3905 (2) | −0.27170 (19) | 0.41756 (16) | 0.0387 (6) | |
H37 | 0.4694 | −0.3063 | 0.4225 | 0.046* | |
C38 | 0.3300 (2) | −0.2161 (2) | 0.33283 (17) | 0.0444 (6) | |
H38 | 0.3682 | −0.2120 | 0.2799 | 0.053* | |
C39 | 0.2141 (2) | −0.16648 (19) | 0.32548 (17) | 0.0433 (6) | |
H39 | 0.1736 | −0.1289 | 0.2675 | 0.052* | |
C40 | 0.1573 (2) | −0.17142 (17) | 0.40182 (16) | 0.0360 (5) | |
H40 | 0.0782 | −0.1375 | 0.3966 | 0.043* | |
C41 | 0.21772 (18) | −0.22685 (16) | 0.48666 (15) | 0.0292 (5) | |
C42 | 0.18096 (17) | −0.24496 (15) | 0.57759 (14) | 0.0262 (5) | |
C43 | 0.07414 (17) | −0.21580 (16) | 0.60712 (15) | 0.0295 (5) | |
H43 | 0.0090 | −0.1782 | 0.5649 | 0.035* | |
C44 | 0.06406 (17) | −0.24229 (16) | 0.69869 (15) | 0.0295 (5) | |
H44 | −0.0090 | −0.2232 | 0.7187 | 0.035* | |
C45 | 0.15895 (17) | −0.29669 (15) | 0.76306 (14) | 0.0257 (5) | |
C46 | 0.26606 (17) | −0.32621 (15) | 0.73185 (14) | 0.0271 (5) | |
H46 | 0.3316 | −0.3629 | 0.7739 | 0.033* | |
C47 | 0.27660 (17) | −0.30221 (15) | 0.64076 (14) | 0.0271 (5) | |
C48 | 0.14490 (16) | −0.32232 (15) | 0.86046 (14) | 0.0247 (4) | |
C49 | 0.22403 (16) | −0.31726 (15) | 0.92071 (14) | 0.0261 (5) | |
H49 | 0.2878 | −0.2954 | 0.8989 | 0.031* | |
C50 | 0.20895 (16) | −0.34417 (15) | 1.01157 (14) | 0.0252 (5) | |
C51 | 0.28110 (18) | −0.34259 (17) | 1.08828 (15) | 0.0299 (5) | |
C52 | 0.22231 (18) | −0.38944 (16) | 1.17006 (15) | 0.0295 (5) | |
C53 | 0.2525 (2) | −0.41327 (18) | 1.26060 (16) | 0.0369 (5) | |
H53 | 0.3198 | −0.4034 | 1.2793 | 0.044* | |
C54 | 0.1828 (2) | −0.45193 (19) | 1.32392 (17) | 0.0437 (6) | |
H54 | 0.2034 | −0.4694 | 1.3863 | 0.052* | |
C55 | 0.0833 (2) | −0.46527 (19) | 1.29676 (16) | 0.0412 (6) | |
H55 | 0.0361 | −0.4909 | 1.3407 | 0.049* | |
C56 | 0.05245 (19) | −0.44147 (17) | 1.20620 (16) | 0.0343 (5) | |
H56 | −0.0156 | −0.4505 | 1.1877 | 0.041* | |
C57 | 0.12285 (17) | −0.40417 (15) | 1.14287 (15) | 0.0278 (5) | |
C58 | 0.11462 (16) | −0.37654 (15) | 1.04451 (14) | 0.0251 (4) | |
C59 | 0.03473 (17) | −0.38021 (16) | 0.98548 (15) | 0.0278 (5) | |
H59 | −0.0297 | −0.4009 | 1.0072 | 0.033* | |
C60 | 0.05033 (17) | −0.35335 (16) | 0.89466 (15) | 0.0285 (5) | |
H60 | −0.0042 | −0.3559 | 0.8544 | 0.034* | |
C61 | 0.48020 (18) | −0.2970 (2) | 0.61827 (17) | 0.0404 (6) | |
H61A | 0.5076 | −0.3364 | 0.6826 | 0.048* | |
H61B | 0.5439 | −0.3135 | 0.5823 | 0.048* | |
C62 | 0.4501 (2) | −0.1860 (2) | 0.60386 (19) | 0.0496 (7) | |
H62A | 0.5170 | −0.1714 | 0.6221 | 0.060* | |
H62B | 0.3883 | −0.1687 | 0.6402 | 0.060* | |
H62C | 0.4257 | −0.1460 | 0.5399 | 0.060* | |
C63 | 0.4234 (2) | −0.44648 (18) | 0.61561 (18) | 0.0442 (6) | |
H63A | 0.4920 | −0.4629 | 0.5841 | 0.053* | |
H63B | 0.4463 | −0.4800 | 0.6812 | 0.053* | |
C64 | 0.3363 (2) | −0.4901 (2) | 0.59015 (19) | 0.0530 (7) | |
H64A | 0.3694 | −0.5630 | 0.6069 | 0.064* | |
H64B | 0.3147 | −0.4592 | 0.5250 | 0.064* | |
H64C | 0.2687 | −0.4761 | 0.6222 | 0.064* | |
C65 | 0.2708 (2) | −0.23223 (19) | 1.07764 (17) | 0.0425 (6) | |
H65A | 0.3184 | −0.2335 | 1.1281 | 0.051* | |
H65B | 0.3022 | −0.2010 | 1.0210 | 0.051* | |
C66 | 0.1507 (2) | −0.16619 (19) | 1.07594 (19) | 0.0508 (7) | |
H66A | 0.1523 | −0.0983 | 1.0687 | 0.061* | |
H66B | 0.1194 | −0.1948 | 1.1327 | 0.061* | |
H66C | 0.1029 | −0.1629 | 1.0254 | 0.061* | |
C67 | 0.40812 (18) | −0.40071 (19) | 1.09331 (16) | 0.0387 (6) | |
H67A | 0.4392 | −0.3662 | 1.0377 | 0.046* | |
H67B | 0.4493 | −0.3974 | 1.1448 | 0.046* | |
C68 | 0.43250 (19) | −0.51055 (19) | 1.10397 (17) | 0.0448 (6) | |
H68A | 0.5147 | −0.5411 | 1.1061 | 0.054* | |
H68B | 0.3937 | −0.5150 | 1.0527 | 0.054* | |
H68C | 0.4048 | −0.5464 | 1.1601 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0391 (13) | 0.0252 (11) | 0.0252 (12) | 0.0006 (9) | 0.0053 (9) | −0.0095 (9) |
C2 | 0.0311 (12) | 0.0310 (12) | 0.0290 (12) | −0.0045 (9) | 0.0046 (9) | −0.0104 (10) |
C3 | 0.0546 (15) | 0.0333 (13) | 0.0322 (14) | −0.0066 (11) | 0.0085 (11) | −0.0144 (11) |
C4 | 0.0557 (16) | 0.0471 (15) | 0.0256 (13) | −0.0171 (12) | 0.0088 (11) | −0.0129 (11) |
C5 | 0.0416 (13) | 0.0330 (13) | 0.0312 (13) | −0.0140 (10) | 0.0007 (10) | −0.0044 (10) |
C6 | 0.0297 (11) | 0.0261 (11) | 0.0327 (13) | −0.0073 (9) | 0.0021 (9) | −0.0085 (10) |
C7 | 0.0207 (10) | 0.0305 (11) | 0.0286 (12) | −0.0065 (8) | 0.0029 (8) | −0.0114 (9) |
C8 | 0.0192 (10) | 0.0266 (11) | 0.0297 (12) | −0.0051 (8) | 0.0033 (8) | −0.0107 (9) |
C9 | 0.0251 (11) | 0.0228 (11) | 0.0331 (13) | −0.0056 (8) | 0.0034 (9) | −0.0100 (9) |
C10 | 0.0262 (11) | 0.0266 (11) | 0.0314 (12) | −0.0060 (9) | 0.0062 (9) | −0.0155 (10) |
C11 | 0.0169 (10) | 0.0290 (11) | 0.0282 (12) | −0.0048 (8) | 0.0012 (8) | −0.0118 (9) |
C12 | 0.0261 (11) | 0.0210 (10) | 0.0299 (12) | −0.0013 (8) | 0.0038 (9) | −0.0078 (9) |
C13 | 0.0217 (10) | 0.0262 (11) | 0.0297 (12) | −0.0007 (8) | 0.0033 (8) | −0.0124 (9) |
C14 | 0.0171 (10) | 0.0270 (11) | 0.0279 (12) | −0.0029 (8) | 0.0017 (8) | −0.0110 (9) |
C15 | 0.0227 (10) | 0.0259 (11) | 0.0299 (12) | −0.0088 (8) | 0.0039 (8) | −0.0104 (9) |
C16 | 0.0221 (10) | 0.0301 (11) | 0.0291 (12) | −0.0095 (9) | 0.0029 (8) | −0.0132 (9) |
C17 | 0.0341 (12) | 0.0375 (13) | 0.0292 (12) | −0.0179 (10) | 0.0065 (9) | −0.0156 (10) |
C18 | 0.0287 (11) | 0.0387 (13) | 0.0308 (13) | −0.0123 (10) | 0.0044 (9) | −0.0135 (10) |
C19 | 0.0458 (14) | 0.0492 (15) | 0.0324 (14) | −0.0195 (12) | 0.0095 (11) | −0.0197 (12) |
C20 | 0.0431 (14) | 0.0605 (17) | 0.0282 (13) | −0.0156 (12) | 0.0116 (11) | −0.0165 (12) |
C21 | 0.0393 (14) | 0.0458 (15) | 0.0354 (14) | −0.0159 (11) | 0.0092 (11) | −0.0058 (12) |
C22 | 0.0379 (13) | 0.0333 (13) | 0.0319 (13) | −0.0123 (10) | 0.0049 (10) | −0.0080 (10) |
C23 | 0.0239 (11) | 0.0317 (12) | 0.0273 (12) | −0.0058 (9) | 0.0027 (9) | −0.0103 (10) |
C24 | 0.0206 (10) | 0.0286 (11) | 0.0258 (12) | −0.0055 (8) | −0.0005 (8) | −0.0082 (9) |
C25 | 0.0329 (12) | 0.0217 (11) | 0.0316 (13) | −0.0070 (9) | 0.0017 (9) | −0.0085 (9) |
C26 | 0.0289 (11) | 0.0277 (11) | 0.0306 (13) | −0.0037 (9) | 0.0028 (9) | −0.0151 (10) |
C27 | 0.0484 (15) | 0.0391 (14) | 0.0310 (14) | 0.0101 (11) | 0.0091 (11) | −0.0123 (11) |
C28 | 0.0306 (14) | 0.0637 (19) | 0.0582 (19) | 0.0000 (13) | 0.0118 (13) | −0.0008 (15) |
C29 | 0.0617 (16) | 0.0244 (12) | 0.0347 (14) | −0.0080 (11) | 0.0088 (12) | −0.0141 (10) |
C30 | 0.0561 (17) | 0.0387 (14) | 0.0562 (18) | −0.0176 (12) | 0.0030 (13) | −0.0221 (13) |
C31 | 0.0426 (14) | 0.0608 (17) | 0.0345 (14) | −0.0299 (13) | 0.0037 (11) | −0.0192 (12) |
C32 | 0.0372 (14) | 0.0680 (19) | 0.0410 (16) | −0.0232 (13) | −0.0058 (11) | −0.0072 (14) |
C33 | 0.0509 (15) | 0.0391 (13) | 0.0378 (14) | −0.0238 (11) | 0.0157 (11) | −0.0231 (11) |
C34 | 0.0472 (15) | 0.0348 (13) | 0.0540 (17) | −0.0097 (11) | 0.0133 (12) | −0.0220 (12) |
C35 | 0.0241 (11) | 0.0402 (13) | 0.0294 (12) | −0.0064 (9) | 0.0059 (9) | −0.0120 (10) |
C36 | 0.0303 (11) | 0.0348 (12) | 0.0322 (13) | −0.0146 (10) | 0.0039 (9) | −0.0128 (10) |
C37 | 0.0361 (13) | 0.0513 (15) | 0.0373 (14) | −0.0200 (11) | 0.0100 (10) | −0.0207 (12) |
C38 | 0.0531 (16) | 0.0619 (17) | 0.0328 (14) | −0.0324 (14) | 0.0138 (12) | −0.0227 (13) |
C39 | 0.0518 (16) | 0.0513 (16) | 0.0314 (14) | −0.0256 (13) | −0.0020 (11) | −0.0121 (12) |
C40 | 0.0364 (13) | 0.0382 (13) | 0.0348 (14) | −0.0144 (10) | −0.0030 (10) | −0.0120 (11) |
C41 | 0.0276 (11) | 0.0304 (12) | 0.0324 (13) | −0.0127 (9) | 0.0008 (9) | −0.0114 (10) |
C42 | 0.0252 (11) | 0.0240 (10) | 0.0288 (12) | −0.0075 (8) | 0.0008 (9) | −0.0087 (9) |
C43 | 0.0211 (10) | 0.0330 (12) | 0.0330 (13) | −0.0055 (9) | −0.0033 (9) | −0.0121 (10) |
C44 | 0.0197 (10) | 0.0332 (12) | 0.0358 (13) | −0.0057 (9) | 0.0034 (9) | −0.0144 (10) |
C45 | 0.0235 (10) | 0.0244 (11) | 0.0299 (12) | −0.0080 (8) | 0.0016 (9) | −0.0101 (9) |
C46 | 0.0198 (10) | 0.0289 (11) | 0.0288 (12) | −0.0049 (8) | −0.0019 (8) | −0.0076 (9) |
C47 | 0.0223 (10) | 0.0274 (11) | 0.0313 (13) | −0.0072 (8) | 0.0018 (9) | −0.0104 (9) |
C48 | 0.0203 (10) | 0.0233 (10) | 0.0285 (12) | −0.0029 (8) | 0.0029 (8) | −0.0097 (9) |
C49 | 0.0198 (10) | 0.0274 (11) | 0.0310 (12) | −0.0083 (8) | 0.0040 (8) | −0.0096 (9) |
C50 | 0.0205 (10) | 0.0229 (10) | 0.0320 (12) | −0.0049 (8) | 0.0017 (8) | −0.0110 (9) |
C51 | 0.0265 (11) | 0.0371 (12) | 0.0297 (12) | −0.0123 (9) | 0.0034 (9) | −0.0141 (10) |
C52 | 0.0277 (11) | 0.0290 (11) | 0.0319 (13) | −0.0052 (9) | 0.0029 (9) | −0.0134 (10) |
C53 | 0.0341 (12) | 0.0464 (14) | 0.0334 (14) | −0.0108 (11) | 0.0014 (10) | −0.0191 (11) |
C54 | 0.0522 (16) | 0.0508 (16) | 0.0275 (13) | −0.0099 (12) | 0.0097 (11) | −0.0179 (12) |
C55 | 0.0468 (15) | 0.0462 (15) | 0.0339 (14) | −0.0154 (12) | 0.0197 (11) | −0.0177 (12) |
C56 | 0.0331 (12) | 0.0361 (13) | 0.0387 (14) | −0.0117 (10) | 0.0130 (10) | −0.0186 (11) |
C57 | 0.0268 (11) | 0.0232 (11) | 0.0333 (12) | −0.0038 (8) | 0.0056 (9) | −0.0128 (9) |
C58 | 0.0230 (10) | 0.0227 (10) | 0.0298 (12) | −0.0051 (8) | 0.0061 (8) | −0.0110 (9) |
C59 | 0.0206 (10) | 0.0301 (11) | 0.0351 (13) | −0.0095 (9) | 0.0072 (9) | −0.0131 (10) |
C60 | 0.0203 (10) | 0.0311 (12) | 0.0352 (13) | −0.0078 (9) | −0.0017 (9) | −0.0131 (10) |
C61 | 0.0207 (11) | 0.0612 (17) | 0.0352 (14) | −0.0096 (11) | 0.0024 (9) | −0.0146 (12) |
C62 | 0.0348 (14) | 0.0692 (19) | 0.0551 (18) | −0.0259 (13) | 0.0044 (12) | −0.0263 (15) |
C63 | 0.0393 (14) | 0.0423 (14) | 0.0397 (15) | 0.0019 (11) | 0.0110 (11) | −0.0125 (12) |
C64 | 0.0702 (19) | 0.0364 (14) | 0.0520 (18) | −0.0134 (13) | 0.0148 (14) | −0.0177 (13) |
C65 | 0.0518 (15) | 0.0493 (15) | 0.0400 (15) | −0.0296 (13) | 0.0086 (12) | −0.0208 (12) |
C66 | 0.0671 (18) | 0.0323 (14) | 0.0549 (18) | −0.0128 (13) | 0.0071 (14) | −0.0195 (13) |
C67 | 0.0236 (11) | 0.0597 (16) | 0.0342 (14) | −0.0142 (11) | 0.0005 (9) | −0.0171 (12) |
C68 | 0.0249 (12) | 0.0565 (16) | 0.0389 (15) | 0.0026 (11) | 0.0001 (10) | −0.0120 (12) |
C1—C2 | 1.528 (3) | C35—C36 | 1.525 (3) |
C1—C13 | 1.530 (3) | C35—C47 | 1.528 (3) |
C1—C29 | 1.541 (3) | C35—C61 | 1.542 (3) |
C1—C27 | 1.547 (3) | C35—C63 | 1.550 (3) |
C2—C3 | 1.387 (3) | C36—C37 | 1.383 (3) |
C2—C7 | 1.397 (3) | C36—C41 | 1.401 (3) |
C3—C4 | 1.397 (3) | C37—C38 | 1.396 (3) |
C3—H3 | 0.9500 | C37—H37 | 0.9500 |
C4—C5 | 1.388 (3) | C38—C39 | 1.392 (4) |
C4—H4 | 0.9500 | C38—H38 | 0.9500 |
C5—C6 | 1.388 (3) | C39—C40 | 1.383 (3) |
C5—H5 | 0.9500 | C39—H39 | 0.9500 |
C6—C7 | 1.389 (3) | C40—C41 | 1.396 (3) |
C6—H6 | 0.9500 | C40—H40 | 0.9500 |
C7—C8 | 1.472 (3) | C41—C42 | 1.466 (3) |
C8—C9 | 1.388 (3) | C42—C43 | 1.393 (3) |
C8—C13 | 1.399 (3) | C42—C47 | 1.407 (3) |
C9—C10 | 1.383 (3) | C43—C44 | 1.383 (3) |
C9—H9 | 0.9500 | C43—H43 | 0.9500 |
C10—C11 | 1.405 (3) | C44—C45 | 1.407 (3) |
C10—H10 | 0.9500 | C44—H44 | 0.9500 |
C11—C12 | 1.402 (3) | C45—C46 | 1.409 (3) |
C11—C14 | 1.483 (3) | C45—C48 | 1.480 (3) |
C12—C13 | 1.384 (3) | C46—C47 | 1.379 (3) |
C12—H12 | 0.9500 | C46—H46 | 0.9500 |
C14—C26 | 1.404 (3) | C48—C60 | 1.408 (3) |
C14—C15 | 1.407 (3) | C48—C49 | 1.408 (3) |
C15—C16 | 1.373 (3) | C49—C50 | 1.383 (3) |
C15—H15 | 0.9500 | C49—H49 | 0.9500 |
C16—C24 | 1.401 (3) | C50—C58 | 1.409 (3) |
C16—C17 | 1.520 (3) | C50—C51 | 1.526 (3) |
C17—C18 | 1.526 (3) | C51—C52 | 1.528 (3) |
C17—C33 | 1.541 (3) | C51—C67 | 1.544 (3) |
C17—C31 | 1.558 (3) | C51—C65 | 1.555 (3) |
C18—C19 | 1.394 (3) | C52—C53 | 1.384 (3) |
C18—C23 | 1.398 (3) | C52—C57 | 1.401 (3) |
C19—C20 | 1.392 (3) | C53—C54 | 1.392 (3) |
C19—H19 | 0.9500 | C53—H53 | 0.9500 |
C20—C21 | 1.387 (4) | C54—C55 | 1.391 (4) |
C20—H20 | 0.9500 | C54—H54 | 0.9500 |
C21—C22 | 1.391 (3) | C55—C56 | 1.386 (3) |
C21—H21 | 0.9500 | C55—H55 | 0.9500 |
C22—C23 | 1.390 (3) | C56—C57 | 1.392 (3) |
C22—H22 | 0.9500 | C56—H56 | 0.9500 |
C23—C24 | 1.472 (3) | C57—C58 | 1.468 (3) |
C24—C25 | 1.386 (3) | C58—C59 | 1.391 (3) |
C25—C26 | 1.389 (3) | C59—C60 | 1.384 (3) |
C25—H25 | 0.9500 | C59—H59 | 0.9500 |
C26—H26 | 0.9500 | C60—H60 | 0.9500 |
C27—C28 | 1.521 (4) | C61—C62 | 1.516 (4) |
C27—H27A | 0.9900 | C61—H61A | 0.9900 |
C27—H27B | 0.9900 | C61—H61B | 0.9900 |
C28—H28A | 0.9800 | C62—H62A | 0.9800 |
C28—H28B | 0.9800 | C62—H62B | 0.9800 |
C28—H28C | 0.9800 | C62—H62C | 0.9800 |
C29—C30 | 1.520 (3) | C63—C64 | 1.524 (4) |
C29—H29A | 0.9900 | C63—H63A | 0.9900 |
C29—H29B | 0.9900 | C63—H63B | 0.9900 |
C30—H30A | 0.9800 | C64—H64A | 0.9800 |
C30—H30B | 0.9800 | C64—H64B | 0.9800 |
C30—H30C | 0.9800 | C64—H64C | 0.9800 |
C31—C32 | 1.521 (4) | C65—C66 | 1.518 (4) |
C31—H31A | 0.9900 | C65—H65A | 0.9900 |
C31—H31B | 0.9900 | C65—H65B | 0.9900 |
C32—H32A | 0.9800 | C66—H66A | 0.9800 |
C32—H32B | 0.9800 | C66—H66B | 0.9800 |
C32—H32C | 0.9800 | C66—H66C | 0.9800 |
C33—C34 | 1.522 (3) | C67—C68 | 1.519 (3) |
C33—H33A | 0.9900 | C67—H67A | 0.9900 |
C33—H33B | 0.9900 | C67—H67B | 0.9900 |
C34—H34A | 0.9800 | C68—H68A | 0.9800 |
C34—H34B | 0.9800 | C68—H68B | 0.9800 |
C34—H34C | 0.9800 | C68—H68C | 0.9800 |
C2—C1—C13 | 100.90 (17) | C36—C35—C47 | 101.28 (17) |
C2—C1—C29 | 111.98 (19) | C36—C35—C61 | 112.77 (19) |
C13—C1—C29 | 111.30 (18) | C47—C35—C61 | 112.22 (19) |
C2—C1—C27 | 111.39 (19) | C36—C35—C63 | 110.72 (19) |
C13—C1—C27 | 110.58 (18) | C47—C35—C63 | 110.34 (18) |
C29—C1—C27 | 110.38 (19) | C61—C35—C63 | 109.32 (19) |
C3—C2—C7 | 120.2 (2) | C37—C36—C41 | 120.1 (2) |
C3—C2—C1 | 128.5 (2) | C37—C36—C35 | 128.9 (2) |
C7—C2—C1 | 111.33 (19) | C41—C36—C35 | 110.94 (19) |
C2—C3—C4 | 118.8 (2) | C36—C37—C38 | 119.4 (2) |
C2—C3—H3 | 120.6 | C36—C37—H37 | 120.3 |
C4—C3—H3 | 120.6 | C38—C37—H37 | 120.3 |
C5—C4—C3 | 120.8 (2) | C39—C38—C37 | 120.3 (2) |
C5—C4—H4 | 119.6 | C39—C38—H38 | 119.8 |
C3—C4—H4 | 119.6 | C37—C38—H38 | 119.8 |
C6—C5—C4 | 120.5 (2) | C40—C39—C38 | 120.6 (2) |
C6—C5—H5 | 119.7 | C40—C39—H39 | 119.7 |
C4—C5—H5 | 119.7 | C38—C39—H39 | 119.7 |
C5—C6—C7 | 118.8 (2) | C39—C40—C41 | 119.2 (2) |
C5—C6—H6 | 120.6 | C39—C40—H40 | 120.4 |
C7—C6—H6 | 120.6 | C41—C40—H40 | 120.4 |
C6—C7—C2 | 121.0 (2) | C40—C41—C36 | 120.3 (2) |
C6—C7—C8 | 130.8 (2) | C40—C41—C42 | 131.2 (2) |
C2—C7—C8 | 108.17 (18) | C36—C41—C42 | 108.52 (19) |
C9—C8—C13 | 119.96 (19) | C43—C42—C47 | 120.0 (2) |
C9—C8—C7 | 131.27 (19) | C43—C42—C41 | 131.43 (19) |
C13—C8—C7 | 108.77 (18) | C47—C42—C41 | 108.61 (18) |
C10—C9—C8 | 119.05 (19) | C44—C43—C42 | 119.20 (19) |
C10—C9—H9 | 120.5 | C44—C43—H43 | 120.4 |
C8—C9—H9 | 120.5 | C42—C43—H43 | 120.4 |
C9—C10—C11 | 121.96 (19) | C43—C44—C45 | 121.89 (19) |
C9—C10—H10 | 119.0 | C43—C44—H44 | 119.1 |
C11—C10—H10 | 119.0 | C45—C44—H44 | 119.1 |
C12—C11—C10 | 118.24 (19) | C44—C45—C46 | 118.03 (19) |
C12—C11—C14 | 121.58 (18) | C44—C45—C48 | 120.27 (18) |
C10—C11—C14 | 120.14 (18) | C46—C45—C48 | 121.70 (18) |
C13—C12—C11 | 119.97 (19) | C47—C46—C45 | 120.52 (19) |
C13—C12—H12 | 120.0 | C47—C46—H46 | 119.7 |
C11—C12—H12 | 120.0 | C45—C46—H46 | 119.7 |
C12—C13—C8 | 120.82 (19) | C46—C47—C42 | 120.34 (19) |
C12—C13—C1 | 128.36 (19) | C46—C47—C35 | 129.15 (19) |
C8—C13—C1 | 110.82 (18) | C42—C47—C35 | 110.50 (18) |
C26—C14—C15 | 117.96 (19) | C60—C48—C49 | 118.57 (19) |
C26—C14—C11 | 121.23 (19) | C60—C48—C45 | 119.50 (18) |
C15—C14—C11 | 120.77 (18) | C49—C48—C45 | 121.93 (18) |
C16—C15—C14 | 120.35 (19) | C50—C49—C48 | 119.98 (18) |
C16—C15—H15 | 119.8 | C50—C49—H49 | 120.0 |
C14—C15—H15 | 119.8 | C48—C49—H49 | 120.0 |
C15—C16—C24 | 120.85 (19) | C49—C50—C58 | 120.47 (19) |
C15—C16—C17 | 128.28 (19) | C49—C50—C51 | 129.25 (18) |
C24—C16—C17 | 110.83 (18) | C58—C50—C51 | 110.26 (18) |
C16—C17—C18 | 101.15 (17) | C50—C51—C52 | 101.41 (17) |
C16—C17—C33 | 113.38 (18) | C50—C51—C67 | 112.91 (18) |
C18—C17—C33 | 113.56 (18) | C52—C51—C67 | 113.67 (19) |
C16—C17—C31 | 109.23 (18) | C50—C51—C65 | 110.23 (18) |
C18—C17—C31 | 110.45 (19) | C52—C51—C65 | 109.73 (18) |
C33—C17—C31 | 108.86 (18) | C67—C51—C65 | 108.73 (18) |
C19—C18—C23 | 119.8 (2) | C53—C52—C57 | 120.2 (2) |
C19—C18—C17 | 129.2 (2) | C53—C52—C51 | 129.0 (2) |
C23—C18—C17 | 110.95 (19) | C57—C52—C51 | 110.72 (19) |
C20—C19—C18 | 118.9 (2) | C52—C53—C54 | 119.1 (2) |
C20—C19—H19 | 120.5 | C52—C53—H53 | 120.4 |
C18—C19—H19 | 120.5 | C54—C53—H53 | 120.4 |
C21—C20—C19 | 120.9 (2) | C55—C54—C53 | 120.6 (2) |
C21—C20—H20 | 119.6 | C55—C54—H54 | 119.7 |
C19—C20—H20 | 119.6 | C53—C54—H54 | 119.7 |
C20—C21—C22 | 120.6 (2) | C56—C55—C54 | 120.6 (2) |
C20—C21—H21 | 119.7 | C56—C55—H55 | 119.7 |
C22—C21—H21 | 119.7 | C54—C55—H55 | 119.7 |
C23—C22—C21 | 118.5 (2) | C55—C56—C57 | 118.8 (2) |
C23—C22—H22 | 120.7 | C55—C56—H56 | 120.6 |
C21—C22—H22 | 120.7 | C57—C56—H56 | 120.6 |
C22—C23—C18 | 121.2 (2) | C56—C57—C52 | 120.6 (2) |
C22—C23—C24 | 130.6 (2) | C56—C57—C58 | 130.9 (2) |
C18—C23—C24 | 108.22 (19) | C52—C57—C58 | 108.44 (18) |
C25—C24—C16 | 119.91 (19) | C59—C58—C50 | 120.14 (19) |
C25—C24—C23 | 131.6 (2) | C59—C58—C57 | 131.10 (19) |
C16—C24—C23 | 108.49 (18) | C50—C58—C57 | 108.74 (18) |
C24—C25—C26 | 119.1 (2) | C60—C59—C58 | 119.15 (19) |
C24—C25—H25 | 120.5 | C60—C59—H59 | 120.4 |
C26—C25—H25 | 120.5 | C58—C59—H59 | 120.4 |
C25—C26—C14 | 121.8 (2) | C59—C60—C48 | 121.68 (19) |
C25—C26—H26 | 119.1 | C59—C60—H60 | 119.2 |
C14—C26—H26 | 119.1 | C48—C60—H60 | 119.2 |
C28—C27—C1 | 114.6 (2) | C62—C61—C35 | 115.13 (19) |
C28—C27—H27A | 108.6 | C62—C61—H61A | 108.5 |
C1—C27—H27A | 108.6 | C35—C61—H61A | 108.5 |
C28—C27—H27B | 108.6 | C62—C61—H61B | 108.5 |
C1—C27—H27B | 108.6 | C35—C61—H61B | 108.5 |
H27A—C27—H27B | 107.6 | H61A—C61—H61B | 107.5 |
C27—C28—H28A | 109.5 | C61—C62—H62A | 109.5 |
C27—C28—H28B | 109.5 | C61—C62—H62B | 109.5 |
H28A—C28—H28B | 109.5 | H62A—C62—H62B | 109.5 |
C27—C28—H28C | 109.5 | C61—C62—H62C | 109.5 |
H28A—C28—H28C | 109.5 | H62A—C62—H62C | 109.5 |
H28B—C28—H28C | 109.5 | H62B—C62—H62C | 109.5 |
C30—C29—C1 | 114.36 (18) | C64—C63—C35 | 115.0 (2) |
C30—C29—H29A | 108.7 | C64—C63—H63A | 108.5 |
C1—C29—H29A | 108.7 | C35—C63—H63A | 108.5 |
C30—C29—H29B | 108.7 | C64—C63—H63B | 108.5 |
C1—C29—H29B | 108.7 | C35—C63—H63B | 108.5 |
H29A—C29—H29B | 107.6 | H63A—C63—H63B | 107.5 |
C29—C30—H30A | 109.5 | C63—C64—H64A | 109.5 |
C29—C30—H30B | 109.5 | C63—C64—H64B | 109.5 |
H30A—C30—H30B | 109.5 | H64A—C64—H64B | 109.5 |
C29—C30—H30C | 109.5 | C63—C64—H64C | 109.5 |
H30A—C30—H30C | 109.5 | H64A—C64—H64C | 109.5 |
H30B—C30—H30C | 109.5 | H64B—C64—H64C | 109.5 |
C32—C31—C17 | 115.2 (2) | C66—C65—C51 | 115.11 (19) |
C32—C31—H31A | 108.5 | C66—C65—H65A | 108.5 |
C17—C31—H31A | 108.5 | C51—C65—H65A | 108.5 |
C32—C31—H31B | 108.5 | C66—C65—H65B | 108.5 |
C17—C31—H31B | 108.5 | C51—C65—H65B | 108.5 |
H31A—C31—H31B | 107.5 | H65A—C65—H65B | 107.5 |
C31—C32—H32A | 109.5 | C65—C66—H66A | 109.5 |
C31—C32—H32B | 109.5 | C65—C66—H66B | 109.5 |
H32A—C32—H32B | 109.5 | H66A—C66—H66B | 109.5 |
C31—C32—H32C | 109.5 | C65—C66—H66C | 109.5 |
H32A—C32—H32C | 109.5 | H66A—C66—H66C | 109.5 |
H32B—C32—H32C | 109.5 | H66B—C66—H66C | 109.5 |
C34—C33—C17 | 115.01 (18) | C68—C67—C51 | 115.13 (19) |
C34—C33—H33A | 108.5 | C68—C67—H67A | 108.5 |
C17—C33—H33A | 108.5 | C51—C67—H67A | 108.5 |
C34—C33—H33B | 108.5 | C68—C67—H67B | 108.5 |
C17—C33—H33B | 108.5 | C51—C67—H67B | 108.5 |
H33A—C33—H33B | 107.5 | H67A—C67—H67B | 107.5 |
C33—C34—H34A | 109.5 | C67—C68—H68A | 109.5 |
C33—C34—H34B | 109.5 | C67—C68—H68B | 109.5 |
H34A—C34—H34B | 109.5 | H68A—C68—H68B | 109.5 |
C33—C34—H34C | 109.5 | C67—C68—H68C | 109.5 |
H34A—C34—H34C | 109.5 | H68A—C68—H68C | 109.5 |
H34B—C34—H34C | 109.5 | H68B—C68—H68C | 109.5 |
C13—C1—C2—C3 | −178.7 (2) | C47—C35—C36—C37 | 178.8 (2) |
C29—C1—C2—C3 | −60.2 (3) | C61—C35—C36—C37 | 58.6 (3) |
C27—C1—C2—C3 | 63.9 (3) | C63—C35—C36—C37 | −64.2 (3) |
C13—C1—C2—C7 | 0.4 (2) | C47—C35—C36—C41 | −2.5 (2) |
C29—C1—C2—C7 | 118.9 (2) | C61—C35—C36—C41 | −122.7 (2) |
C27—C1—C2—C7 | −116.9 (2) | C63—C35—C36—C41 | 114.5 (2) |
C7—C2—C3—C4 | −0.9 (4) | C41—C36—C37—C38 | 1.5 (3) |
C1—C2—C3—C4 | 178.1 (2) | C35—C36—C37—C38 | −179.9 (2) |
C2—C3—C4—C5 | 0.1 (4) | C36—C37—C38—C39 | −0.9 (4) |
C3—C4—C5—C6 | 0.5 (4) | C37—C38—C39—C40 | 0.1 (4) |
C4—C5—C6—C7 | −0.3 (3) | C38—C39—C40—C41 | 0.0 (4) |
C5—C6—C7—C2 | −0.5 (3) | C39—C40—C41—C36 | 0.6 (3) |
C5—C6—C7—C8 | −178.3 (2) | C39—C40—C41—C42 | 179.8 (2) |
C3—C2—C7—C6 | 1.1 (3) | C37—C36—C41—C40 | −1.4 (3) |
C1—C2—C7—C6 | −178.08 (19) | C35—C36—C41—C40 | 179.8 (2) |
C3—C2—C7—C8 | 179.3 (2) | C37—C36—C41—C42 | 179.2 (2) |
C1—C2—C7—C8 | 0.1 (2) | C35—C36—C41—C42 | 0.4 (2) |
C6—C7—C8—C9 | −2.0 (4) | C40—C41—C42—C43 | 2.9 (4) |
C2—C7—C8—C9 | −180.0 (2) | C36—C41—C42—C43 | −177.9 (2) |
C6—C7—C8—C13 | 177.2 (2) | C40—C41—C42—C47 | −177.1 (2) |
C2—C7—C8—C13 | −0.7 (2) | C36—C41—C42—C47 | 2.2 (2) |
C13—C8—C9—C10 | −0.6 (3) | C47—C42—C43—C44 | 1.1 (3) |
C7—C8—C9—C10 | 178.6 (2) | C41—C42—C43—C44 | −178.8 (2) |
C8—C9—C10—C11 | −0.1 (3) | C42—C43—C44—C45 | 0.9 (3) |
C9—C10—C11—C12 | 0.6 (3) | C43—C44—C45—C46 | −1.5 (3) |
C9—C10—C11—C14 | −177.13 (19) | C43—C44—C45—C48 | 179.1 (2) |
C10—C11—C12—C13 | −0.5 (3) | C44—C45—C46—C47 | −0.1 (3) |
C14—C11—C12—C13 | 177.22 (18) | C48—C45—C46—C47 | 179.35 (19) |
C11—C12—C13—C8 | −0.1 (3) | C45—C46—C47—C42 | 2.1 (3) |
C11—C12—C13—C1 | −179.8 (2) | C45—C46—C47—C35 | −176.5 (2) |
C9—C8—C13—C12 | 0.7 (3) | C43—C42—C47—C46 | −2.7 (3) |
C7—C8—C13—C12 | −178.66 (19) | C41—C42—C47—C46 | 177.29 (19) |
C9—C8—C13—C1 | −179.60 (19) | C43—C42—C47—C35 | 176.16 (19) |
C7—C8—C13—C1 | 1.0 (2) | C41—C42—C47—C35 | −3.9 (2) |
C2—C1—C13—C12 | 178.8 (2) | C36—C35—C47—C46 | −177.4 (2) |
C29—C1—C13—C12 | 59.8 (3) | C61—C35—C47—C46 | −56.9 (3) |
C27—C1—C13—C12 | −63.3 (3) | C63—C35—C47—C46 | 65.3 (3) |
C2—C1—C13—C8 | −0.9 (2) | C36—C35—C47—C42 | 3.9 (2) |
C29—C1—C13—C8 | −119.9 (2) | C61—C35—C47—C42 | 124.4 (2) |
C27—C1—C13—C8 | 117.1 (2) | C63—C35—C47—C42 | −113.4 (2) |
C12—C11—C14—C26 | −28.5 (3) | C44—C45—C48—C60 | 40.5 (3) |
C10—C11—C14—C26 | 149.19 (19) | C46—C45—C48—C60 | −138.9 (2) |
C12—C11—C14—C15 | 153.81 (19) | C44—C45—C48—C49 | −139.9 (2) |
C10—C11—C14—C15 | −28.5 (3) | C46—C45—C48—C49 | 40.7 (3) |
C26—C14—C15—C16 | −1.6 (3) | C60—C48—C49—C50 | 1.1 (3) |
C11—C14—C15—C16 | 176.17 (18) | C45—C48—C49—C50 | −178.48 (19) |
C14—C15—C16—C24 | 0.0 (3) | C48—C49—C50—C58 | −0.1 (3) |
C14—C15—C16—C17 | 177.69 (19) | C48—C49—C50—C51 | −178.5 (2) |
C15—C16—C17—C18 | 176.2 (2) | C49—C50—C51—C52 | −175.5 (2) |
C24—C16—C17—C18 | −5.9 (2) | C58—C50—C51—C52 | 6.0 (2) |
C15—C16—C17—C33 | 54.3 (3) | C49—C50—C51—C67 | −53.5 (3) |
C24—C16—C17—C33 | −127.80 (19) | C58—C50—C51—C67 | 128.04 (19) |
C15—C16—C17—C31 | −67.3 (3) | C49—C50—C51—C65 | 68.4 (3) |
C24—C16—C17—C31 | 110.6 (2) | C58—C50—C51—C65 | −110.1 (2) |
C16—C17—C18—C19 | −175.7 (2) | C50—C51—C52—C53 | 176.2 (2) |
C33—C17—C18—C19 | −53.9 (3) | C67—C51—C52—C53 | 54.7 (3) |
C31—C17—C18—C19 | 68.7 (3) | C65—C51—C52—C53 | −67.2 (3) |
C16—C17—C18—C23 | 5.7 (2) | C50—C51—C52—C57 | −6.3 (2) |
C33—C17—C18—C23 | 127.6 (2) | C67—C51—C52—C57 | −127.8 (2) |
C31—C17—C18—C23 | −109.8 (2) | C65—C51—C52—C57 | 110.2 (2) |
C23—C18—C19—C20 | 0.0 (3) | C57—C52—C53—C54 | 0.0 (3) |
C17—C18—C19—C20 | −178.4 (2) | C51—C52—C53—C54 | 177.3 (2) |
C18—C19—C20—C21 | 0.8 (4) | C52—C53—C54—C55 | −0.9 (4) |
C19—C20—C21—C22 | −0.8 (4) | C53—C54—C55—C56 | 0.8 (4) |
C20—C21—C22—C23 | −0.1 (4) | C54—C55—C56—C57 | 0.1 (3) |
C21—C22—C23—C18 | 0.9 (3) | C55—C56—C57—C52 | −1.0 (3) |
C21—C22—C23—C24 | −177.2 (2) | C55—C56—C57—C58 | 177.4 (2) |
C19—C18—C23—C22 | −0.9 (3) | C53—C52—C57—C56 | 0.9 (3) |
C17—C18—C23—C22 | 177.8 (2) | C51—C52—C57—C56 | −176.79 (19) |
C19—C18—C23—C24 | 177.6 (2) | C53—C52—C57—C58 | −177.81 (19) |
C17—C18—C23—C24 | −3.7 (2) | C51—C52—C57—C58 | 4.5 (2) |
C15—C16—C24—C25 | 1.6 (3) | C49—C50—C58—C59 | −1.0 (3) |
C17—C16—C24—C25 | −176.48 (18) | C51—C50—C58—C59 | 177.66 (18) |
C15—C16—C24—C23 | −177.86 (18) | C49—C50—C58—C57 | 177.56 (18) |
C17—C16—C24—C23 | 4.1 (2) | C51—C50—C58—C57 | −3.8 (2) |
C22—C23—C24—C25 | −1.3 (4) | C56—C57—C58—C59 | −0.6 (4) |
C18—C23—C24—C25 | −179.6 (2) | C52—C57—C58—C59 | 177.9 (2) |
C22—C23—C24—C16 | 178.1 (2) | C56—C57—C58—C50 | −179.0 (2) |
C18—C23—C24—C16 | −0.2 (2) | C52—C57—C58—C50 | −0.4 (2) |
C16—C24—C25—C26 | −1.5 (3) | C50—C58—C59—C60 | 1.1 (3) |
C23—C24—C25—C26 | 177.9 (2) | C57—C58—C59—C60 | −177.1 (2) |
C24—C25—C26—C14 | −0.2 (3) | C58—C59—C60—C48 | −0.1 (3) |
C15—C14—C26—C25 | 1.7 (3) | C49—C48—C60—C59 | −1.0 (3) |
C11—C14—C26—C25 | −176.03 (19) | C45—C48—C60—C59 | 178.57 (19) |
C2—C1—C27—C28 | 61.6 (3) | C36—C35—C61—C62 | 59.2 (3) |
C13—C1—C27—C28 | −49.7 (3) | C47—C35—C61—C62 | −54.4 (3) |
C29—C1—C27—C28 | −173.3 (2) | C63—C35—C61—C62 | −177.2 (2) |
C2—C1—C29—C30 | −57.2 (3) | C36—C35—C63—C64 | −52.6 (3) |
C13—C1—C29—C30 | 54.9 (3) | C47—C35—C63—C64 | 58.7 (3) |
C27—C1—C29—C30 | 178.1 (2) | C61—C35—C63—C64 | −177.4 (2) |
C16—C17—C31—C32 | −50.0 (3) | C50—C51—C65—C66 | 58.4 (3) |
C18—C17—C31—C32 | 60.4 (3) | C52—C51—C65—C66 | −52.5 (3) |
C33—C17—C31—C32 | −174.3 (2) | C67—C51—C65—C66 | −177.4 (2) |
C16—C17—C33—C34 | 54.3 (3) | C50—C51—C67—C68 | −57.4 (3) |
C18—C17—C33—C34 | −60.5 (3) | C52—C51—C67—C68 | 57.4 (3) |
C31—C17—C33—C34 | 176.0 (2) | C65—C51—C67—C68 | 179.9 (2) |
Cg3 and Cg4 are the centroids of the C14–C16/C24–C26 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C43—H43···Cg3i | 0.95 | 2.64 | 3.49 | 150 |
C60—H60···Cg4i | 0.95 | 3.15 | 3.83 | 130 |
Symmetry code: (i) −x, −y, −z+1. |
Cg3 and Cg4 are the centroids of the C14–C16/C24–C26 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C43—H43···Cg3i | 0.95 | 2.64 | 3.49 | 150 |
C60—H60···Cg4i | 0.95 | 3.15 | 3.83 | 130 |
Symmetry code: (i) −x, −y, −z+1. |
Acknowledgements
This study was supported by a 2013 Research Grant from Kangwon National University (No. 120131375).
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As a potential conductive small molecule, 2,2'-bi(9,9-diethylfluorene) is regarded as one of the most promising candidate materials for organic electronics due to its unique photophysical properties, good thermal stability as well as a stable glass phase at room temperature (Chao et al., 2005; Hapiot et al., 2005). Therefore, the crystal structure of 2,2'-bi(9,9-diethylfluorene) plays key role in understanding the reasons that this compound has a high thermal stability and a stable glass form (Gong & Lagowski, 2008).
The title compound (Scheme 1, Fig.1) crystallized with two crystallographically independent molecules (A and B) in the asymmetric unit, which differ mainly in the orientation of the lateral ethyl chains in each molecule. The ethyl substituents in A are found on the same side of the molecule whereas in molecule B one diethylfluorene moiety has undergone a 180° rotation such that the two pairs of ethyl residues appear on opposite sides of the molecule. In both molecules the fluorene segments are planar with a maximum r.m.s. deviation of 0.048 ° for the C48–C60 ring system. The ethyl chains (excluding H atoms) are also planar, with each pair almost perpendicular to the plane of the fluorene system to which they are attached, with dihedral angles between the ethyl and fluorene planes in the range 86.04 (8)° to 89.5 (1)°. This interruption of π-conjugation of two fluorene segments may be caused by intermolecular intermolecular C—H···π interactions between neighboring molecules (Table 1). All bond lengths and bond angles are normal and comparable to those of observed in the structures of other fluorene derivatives (Han et al., 2006; Jasinski et al., 2003; Suchod et al., 2000).