Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001499/qa0213sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001499/qa0213Isup2.hkl |
CCDC reference: 143328
The title compound was obtained via Ni-catalyzed coupling of 2-bromo-9,9-dihexylfluorene monomeric units. The hexyl chains are grafted in order to allow a high solubility in common organic solvents.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: Xtal3.2 SORTRF ADDREF (Hall et al., 1992); program(s) used to solve structure: Xtal3.2 GENTAN; program(s) used to refine structure: Xtal3.2 CRYLSQ; molecular graphics: Xtal3.2 ORTEP; software used to prepare material for publication: Xtal3.2 BONDLA CIFIO.
C50H66 | F(000) = 1463.83 |
Mr = 667.08 | Dx = 1.043 Mg m−3 |
Monoclinic, P21/n | Melting point: 333 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 15.975 (2) Å | Cell parameters from 20 reflections |
b = 15.773 (2) Å | θ = 10–12° |
c = 17.142 (2) Å | µ = 0.06 mm−1 |
β = 100.51 (1)° | T = 293 K |
V = 4246.9 (7) Å3 | Parallelepiped, translucent white |
Z = 4 | 0.3 × 0.3 × 0.2 mm |
Enraf-Nonius CAD-4 diffractometer | θmax = 25.0°, θmin = 2.1° |
ω scans | h = −18→18 |
7842 measured reflections | k = −5→18 |
7460 independent reflections | l = −4→20 |
4526 reflections with refl observed if Inet > .540 σ(Inet) | 2 standard reflections every 100 reflections |
Rint = 0.017 | intensity decay: 1% |
Refinement on F | 0 constraints |
Least-squares matrix: full | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.100 | w = 1/(0.1 + 1.4σ2) |
wR(F2) = 0.039 | (Δ/σ)max = 0.003 |
S = 1.27 | Δρmax = 0.35 e Å−3 |
4526 reflections | Δρmin = −0.41 e Å−3 |
452 parameters | Extinction correction: Zachariasen (1967), Eq22, p. 292_"Cryst._Comp."_Munksgaard_1970 |
0 restraints | Extinction coefficient: 0.72 (3) |
C50H66 | V = 4246.9 (7) Å3 |
Mr = 667.08 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.975 (2) Å | µ = 0.06 mm−1 |
b = 15.773 (2) Å | T = 293 K |
c = 17.142 (2) Å | 0.3 × 0.3 × 0.2 mm |
β = 100.51 (1)° |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.017 |
7842 measured reflections | 2 standard reflections every 100 reflections |
7460 independent reflections | intensity decay: 1% |
4526 reflections with refl observed if Inet > .540 σ(Inet) |
R[F2 > 2σ(F2)] = 0.100 | 0 restraints |
wR(F2) = 0.039 | H-atom parameters not refined |
S = 1.27 | Δρmax = 0.35 e Å−3 |
4526 reflections | Δρmin = −0.41 e Å−3 |
452 parameters |
x | y | z | Uiso*/Ueq | ||
C101 | 0.9304 (2) | 0.6177 (2) | 0.2301 (2) | 0.046 (2) | |
C102 | 0.9763 (2) | 0.6464 (2) | 0.3034 (2) | 0.043 (2) | |
C103 | 0.9554 (2) | 0.6098 (3) | 0.3718 (2) | 0.057 (3) | |
C104 | 0.8935 (2) | 0.5481 (3) | 0.3689 (2) | 0.061 (3) | |
C105 | 0.7405 (3) | 0.4071 (3) | 0.3221 (2) | 0.065 (3) | |
C106 | 0.6770 (3) | 0.3530 (3) | 0.2844 (3) | 0.078 (3) | |
C107 | 0.6555 (3) | 0.3496 (3) | 0.2031 (3) | 0.079 (3) | |
C108 | 0.6960 (3) | 0.4011 (3) | 0.1567 (2) | 0.071 (3) | |
C109 | 0.8112 (2) | 0.5196 (2) | 0.1541 (2) | 0.052 (3) | |
C110 | 0.8688 (2) | 0.5565 (2) | 0.2277 (2) | 0.043 (2) | |
C111 | 0.8497 (2) | 0.5217 (2) | 0.2964 (2) | 0.048 (3) | |
C112 | 0.7817 (2) | 0.4587 (2) | 0.2754 (2) | 0.053 (3) | |
C113 | 0.7594 (2) | 0.4561 (2) | 0.1927 (2) | 0.055 (3) | |
C114 | 0.8625 (2) | 0.4777 (2) | 0.0967 (2) | 0.060 (3) | |
C115 | 0.9264 (2) | 0.4103 (3) | 0.1320 (2) | 0.066 (3) | |
C116 | 0.9696 (3) | 0.3681 (3) | 0.0709 (2) | 0.081 (3) | |
C117 | 1.0327 (3) | 0.3001 (3) | 0.1046 (3) | 0.085 (4) | |
C118 | 1.0777 (3) | 0.2595 (4) | 0.0442 (4) | 0.141 (5) | |
C119 | 1.1389 (4) | 0.1908 (4) | 0.0761 (4) | 0.182 (6) | |
C120 | 0.7540 (2) | 0.5889 (2) | 0.1084 (2) | 0.056 (3) | |
C121 | 0.7009 (2) | 0.6403 (2) | 0.1559 (2) | 0.058 (3) | |
C122 | 0.6412 (2) | 0.7020 (2) | 0.1045 (2) | 0.060 (3) | |
C123 | 0.5864 (2) | 0.7537 (3) | 0.1505 (2) | 0.064 (3) | |
C124 | 0.5255 (3) | 0.8126 (3) | 0.0971 (2) | 0.074 (3) | |
C125 | 0.4681 (3) | 0.8653 (3) | 0.1395 (3) | 0.090 (4) | |
C201 | 1.0636 (2) | 0.7474 (2) | 0.2393 (2) | 0.043 (2) | |
C202 | 1.0427 (2) | 0.7119 (2) | 0.3077 (2) | 0.039 (2) | |
C203 | 1.0876 (2) | 0.7406 (3) | 0.3803 (2) | 0.056 (3) | |
C204 | 1.1498 (2) | 0.8025 (3) | 0.3856 (2) | 0.059 (3) | |
C205 | 1.2869 (3) | 0.9496 (3) | 0.3571 (2) | 0.063 (3) | |
C206 | 1.3379 (3) | 1.0087 (3) | 0.3277 (3) | 0.075 (3) | |
C207 | 1.3315 (3) | 1.0207 (3) | 0.2475 (3) | 0.078 (3) | |
C208 | 1.2740 (3) | 0.9735 (3) | 0.1938 (2) | 0.068 (3) | |
C209 | 1.1565 (2) | 0.8549 (2) | 0.1770 (2) | 0.047 (2) | |
C210 | 1.1256 (2) | 0.8093 (2) | 0.2443 (2) | 0.041 (2) | |
C211 | 1.1697 (2) | 0.8371 (2) | 0.3179 (2) | 0.043 (2) | |
C212 | 1.2297 (2) | 0.9021 (2) | 0.3040 (2) | 0.047 (2) | |
C213 | 1.2234 (2) | 0.9138 (2) | 0.2224 (2) | 0.049 (3) | |
C214 | 1.1952 (2) | 0.7932 (2) | 0.1232 (2) | 0.053 (3) | |
C215 | 1.2644 (2) | 0.7332 (2) | 0.1650 (2) | 0.053 (3) | |
C216 | 1.3009 (2) | 0.6805 (2) | 0.1049 (2) | 0.060 (3) | |
C217 | 1.3702 (2) | 0.6192 (2) | 0.1420 (2) | 0.056 (3) | |
C218 | 1.4068 (3) | 0.5693 (3) | 0.0802 (2) | 0.072 (3) | |
C219 | 1.4774 (3) | 0.5078 (3) | 0.1138 (2) | 0.083 (3) | |
C220 | 1.0839 (2) | 0.9047 (2) | 0.1239 (2) | 0.052 (2) | |
C221 | 1.0350 (2) | 0.9665 (2) | 0.1669 (2) | 0.057 (3) | |
C222 | 0.9635 (2) | 1.0094 (2) | 0.1100 (2) | 0.061 (3) | |
C223 | 0.9139 (2) | 1.0744 (2) | 0.1483 (2) | 0.060 (3) | |
C224 | 0.8460 (3) | 1.1181 (3) | 0.0877 (2) | 0.082 (3) | |
C225 | 0.7951 (3) | 1.1856 (3) | 0.1210 (2) | 0.087 (3) | |
H101 | 0.94291 | 0.64153 | 0.17980 | 0.08000* | |
H103 | 0.98709 | 0.62909 | 0.42494 | 0.08000* | |
H104 | 0.88040 | 0.52340 | 0.41924 | 0.08000* | |
H105 | 0.75652 | 0.40843 | 0.38127 | 0.08000* | |
H106 | 0.64584 | 0.31705 | 0.31797 | 0.08000* | |
H107 | 0.61057 | 0.30909 | 0.17800 | 0.08000* | |
H108 | 0.68017 | 0.39934 | 0.09712 | 0.08000* | |
H114a | 0.82110 | 0.45111 | 0.05313 | 0.08000* | |
H114b | 0.89427 | 0.52394 | 0.07497 | 0.08000* | |
H115a | 0.97089 | 0.43791 | 0.17246 | 0.08000* | |
H115b | 0.89584 | 0.36631 | 0.15749 | 0.08000* | |
H116a | 0.92480 | 0.34151 | 0.02960 | 0.08000* | |
H116b | 1.00041 | 0.41251 | 0.04528 | 0.08000* | |
H117a | 1.07717 | 0.32580 | 0.14669 | 0.08000* | |
H117b | 1.00228 | 0.25428 | 0.12815 | 0.08000* | |
H118a | 1.03356 | 0.23619 | −0.00105 | 0.08000* | |
H118b | 1.11019 | 0.30565 | 0.01970 | 0.08000* | |
H120a | 0.79218 | 0.62928 | 0.08651 | 0.08000* | |
H120b | 0.71455 | 0.56114 | 0.06411 | 0.08000* | |
H121a | 0.66614 | 0.60017 | 0.18196 | 0.08000* | |
H121b | 0.74003 | 0.67293 | 0.19720 | 0.08000* | |
H122a | 0.67663 | 0.74195 | 0.07928 | 0.08000* | |
H122b | 0.60315 | 0.66882 | 0.06311 | 0.08000* | |
H123a | 0.55228 | 0.71354 | 0.17730 | 0.08000* | |
H123b | 0.62444 | 0.78805 | 0.19102 | 0.08000* | |
H124a | 0.56043 | 0.85266 | 0.07077 | 0.08000* | |
H124b | 0.48881 | 0.77767 | 0.05593 | 0.08000* | |
H119a | 1.18318 | 0.21438 | 0.11894 | 0.08000* | |
H119b | 1.10655 | 0.14493 | 0.09819 | 0.08000* | |
H119c | 1.16836 | 0.16418 | 0.03476 | 0.08000* | |
H125a | 0.43324 | 0.82528 | 0.16592 | 0.08000* | |
H125b | 0.50485 | 0.90027 | 0.18076 | 0.08000* | |
H125c | 0.42816 | 0.90408 | 0.10476 | 0.08000* | |
H201 | 1.03355 | 0.72787 | 0.18600 | 0.08000* | |
H203 | 1.07449 | 0.71613 | 0.43065 | 0.08000* | |
H204 | 1.18019 | 0.82218 | 0.43901 | 0.08000* | |
H205 | 1.29195 | 0.94171 | 0.41565 | 0.08000* | |
H206 | 1.37929 | 1.04291 | 0.36581 | 0.08000* | |
H207 | 1.36853 | 1.06400 | 0.22757 | 0.08000* | |
H208 | 1.26889 | 0.98217 | 0.13495 | 0.08000* | |
H214a | 1.14728 | 0.75792 | 0.09410 | 0.08000* | |
H214b | 1.21989 | 0.82803 | 0.08436 | 0.08000* | |
H215a | 1.31065 | 0.76759 | 0.19712 | 0.08000* | |
H215b | 1.23887 | 0.69468 | 0.20065 | 0.08000* | |
H216a | 1.25350 | 0.64728 | 0.07292 | 0.08000* | |
H216b | 1.32538 | 0.72013 | 0.06950 | 0.08000* | |
H217a | 1.41720 | 0.65187 | 0.17476 | 0.08000* | |
H217b | 1.34560 | 0.57822 | 0.17590 | 0.08000* | |
H218a | 1.36004 | 0.53574 | 0.04757 | 0.08000* | |
H218b | 1.43067 | 0.61011 | 0.04537 | 0.08000* | |
H220a | 1.10949 | 0.93761 | 0.08432 | 0.08000* | |
H220b | 1.04244 | 0.86251 | 0.09582 | 0.08000* | |
H221a | 1.01037 | 0.93469 | 0.20774 | 0.08000* | |
H221b | 1.07529 | 1.01066 | 0.19327 | 0.08000* | |
H222a | 0.98901 | 1.03830 | 0.06797 | 0.08000* | |
H222b | 0.92318 | 0.96434 | 0.08514 | 0.08000* | |
H223a | 0.88521 | 1.04527 | 0.18786 | 0.08000* | |
H223b | 0.95395 | 1.11823 | 0.17502 | 0.08000* | |
H224a | 0.87488 | 1.14543 | 0.04674 | 0.08000* | |
H224b | 0.80549 | 1.07384 | 0.06126 | 0.08000* | |
H219a | 1.52486 | 0.54194 | 0.14708 | 0.08300* | |
H219b | 1.45446 | 0.46754 | 0.15016 | 0.08300* | |
H219c | 1.49761 | 0.47845 | 0.07112 | 0.08300* | |
H225a | 0.76634 | 1.15764 | 0.16095 | 0.08000* | |
H225b | 0.83573 | 1.22923 | 0.14643 | 0.08000* | |
H225c | 0.75077 | 1.21370 | 0.08053 | 0.08000* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C101 | 0.046 (2) | 0.050 (3) | 0.043 (2) | −0.002 (2) | 0.009 (2) | 0.004 (2) |
C102 | 0.042 (2) | 0.039 (2) | 0.047 (2) | −0.001 (2) | 0.008 (2) | −0.001 (2) |
C103 | 0.066 (3) | 0.063 (3) | 0.038 (2) | −0.015 (2) | 0.002 (2) | −0.003 (2) |
C104 | 0.067 (3) | 0.065 (3) | 0.052 (3) | −0.021 (2) | 0.015 (2) | 0.001 (2) |
C105 | 0.063 (3) | 0.054 (3) | 0.077 (3) | −0.002 (3) | 0.016 (3) | 0.009 (3) |
C106 | 0.074 (4) | 0.054 (3) | 0.112 (4) | −0.005 (3) | 0.033 (3) | 0.014 (3) |
C107 | 0.059 (3) | 0.056 (3) | 0.124 (4) | −0.025 (3) | 0.017 (3) | 0.005 (3) |
C108 | 0.062 (3) | 0.058 (3) | 0.088 (3) | −0.015 (3) | −0.002 (3) | 0.000 (3) |
C109 | 0.049 (3) | 0.056 (3) | 0.050 (3) | −0.015 (2) | 0.006 (2) | 0.004 (2) |
C110 | 0.047 (3) | 0.038 (2) | 0.045 (3) | −0.005 (2) | 0.012 (2) | 0.005 (2) |
C111 | 0.043 (3) | 0.043 (3) | 0.058 (3) | −0.007 (2) | 0.013 (2) | 0.002 (2) |
C112 | 0.046 (3) | 0.044 (3) | 0.070 (3) | −0.003 (2) | 0.016 (2) | 0.007 (2) |
C113 | 0.048 (3) | 0.046 (3) | 0.070 (3) | −0.001 (2) | 0.010 (2) | 0.004 (2) |
C114 | 0.063 (3) | 0.061 (3) | 0.053 (3) | −0.010 (2) | 0.004 (2) | −0.014 (2) |
C115 | 0.062 (3) | 0.062 (3) | 0.073 (3) | −0.006 (2) | 0.012 (2) | −0.007 (3) |
C116 | 0.074 (3) | 0.080 (4) | 0.087 (4) | −0.014 (3) | 0.011 (3) | −0.028 (3) |
C117 | 0.063 (3) | 0.070 (4) | 0.127 (4) | −0.004 (3) | 0.027 (3) | −0.020 (3) |
C118 | 0.093 (5) | 0.123 (6) | 0.208 (7) | −0.007 (4) | 0.027 (4) | −0.084 (5) |
C119 | 0.107 (5) | 0.122 (6) | 0.332 (9) | −0.028 (4) | 0.080 (5) | −0.111 (6) |
C120 | 0.059 (3) | 0.060 (3) | 0.046 (2) | −0.012 (2) | 0.000 (2) | −0.001 (2) |
C121 | 0.053 (3) | 0.061 (3) | 0.058 (3) | −0.006 (2) | 0.006 (2) | 0.009 (2) |
C122 | 0.061 (3) | 0.061 (3) | 0.056 (3) | 0.000 (2) | 0.003 (2) | 0.001 (2) |
C123 | 0.061 (3) | 0.072 (3) | 0.058 (3) | −0.007 (3) | 0.009 (2) | 0.007 (2) |
C124 | 0.067 (3) | 0.083 (4) | 0.070 (3) | 0.007 (3) | 0.007 (2) | 0.003 (3) |
C125 | 0.077 (4) | 0.081 (4) | 0.116 (4) | 0.005 (3) | 0.026 (3) | 0.001 (3) |
C201 | 0.043 (2) | 0.046 (3) | 0.038 (2) | −0.006 (2) | 0.003 (2) | −0.003 (2) |
C202 | 0.041 (2) | 0.035 (2) | 0.041 (2) | 0.001 (2) | 0.004 (2) | −0.000 (2) |
C203 | 0.065 (3) | 0.062 (3) | 0.040 (3) | −0.013 (2) | 0.007 (2) | 0.002 (2) |
C204 | 0.062 (3) | 0.073 (3) | 0.037 (2) | −0.017 (2) | −0.000 (2) | −0.004 (2) |
C205 | 0.060 (3) | 0.055 (3) | 0.072 (3) | −0.008 (2) | 0.005 (2) | −0.007 (2) |
C206 | 0.054 (3) | 0.058 (3) | 0.106 (4) | −0.004 (3) | −0.005 (3) | −0.024 (3) |
C207 | 0.062 (3) | 0.049 (3) | 0.125 (4) | −0.016 (3) | 0.023 (3) | −0.008 (3) |
C208 | 0.074 (3) | 0.064 (3) | 0.070 (3) | −0.016 (3) | 0.020 (3) | −0.001 (3) |
C209 | 0.053 (3) | 0.048 (3) | 0.042 (2) | −0.007 (2) | 0.010 (2) | −0.003 (2) |
C210 | 0.041 (2) | 0.041 (3) | 0.041 (2) | 0.003 (2) | 0.007 (2) | −0.002 (2) |
C211 | 0.037 (2) | 0.045 (3) | 0.047 (3) | 0.003 (2) | 0.004 (2) | −0.004 (2) |
C212 | 0.038 (2) | 0.043 (3) | 0.059 (3) | −0.001 (2) | 0.007 (2) | −0.007 (2) |
C213 | 0.044 (3) | 0.046 (3) | 0.059 (3) | 0.001 (2) | 0.011 (2) | −0.001 (2) |
C214 | 0.053 (3) | 0.050 (3) | 0.054 (3) | −0.003 (2) | 0.009 (2) | 0.001 (2) |
C215 | 0.057 (3) | 0.055 (3) | 0.050 (3) | 0.001 (2) | 0.014 (2) | 0.001 (2) |
C216 | 0.056 (3) | 0.058 (3) | 0.064 (3) | −0.000 (2) | 0.008 (2) | −0.004 (2) |
C217 | 0.053 (3) | 0.057 (3) | 0.059 (3) | −0.006 (2) | 0.008 (2) | −0.007 (2) |
C218 | 0.073 (3) | 0.075 (4) | 0.069 (3) | 0.010 (3) | 0.014 (2) | −0.008 (3) |
C219 | 0.087 (4) | 0.085 (4) | 0.078 (3) | 0.015 (3) | 0.019 (3) | −0.000 (3) |
C220 | 0.058 (3) | 0.049 (3) | 0.048 (2) | 0.003 (2) | 0.007 (2) | 0.005 (2) |
C221 | 0.060 (3) | 0.055 (3) | 0.054 (3) | 0.008 (2) | 0.008 (2) | 0.003 (2) |
C222 | 0.066 (3) | 0.065 (3) | 0.053 (3) | 0.006 (2) | 0.008 (2) | 0.004 (2) |
C223 | 0.068 (3) | 0.061 (3) | 0.053 (3) | 0.006 (2) | 0.015 (2) | 0.005 (2) |
C224 | 0.098 (4) | 0.079 (4) | 0.069 (3) | 0.029 (3) | 0.015 (3) | 0.006 (3) |
C225 | 0.092 (4) | 0.081 (4) | 0.090 (4) | 0.018 (3) | 0.021 (3) | 0.020 (3) |
C101—C102 | 1.409 (5) | C201—C202 | 1.394 (5) |
C101—C110 | 1.374 (5) | C201—C210 | 1.383 (5) |
C101—H101 | 0.993 (4) | C201—H201 | 1.000 (3) |
C102—C103 | 1.402 (5) | C202—C203 | 1.393 (5) |
C102—C202 | 1.472 (5) | C203—C204 | 1.385 (6) |
C103—C104 | 1.382 (6) | C203—H203 | 1.002 (4) |
C103—H103 | 1.005 (3) | C204—C211 | 1.371 (5) |
C104—C111 | 1.375 (5) | C204—H204 | 1.004 (3) |
C104—H104 | 1.003 (4) | C205—C206 | 1.391 (6) |
C105—C106 | 1.392 (6) | C205—C212 | 1.386 (5) |
C105—C112 | 1.388 (6) | C205—H205 | 1.000 (4) |
C105—H105 | 1.000 (4) | C206—C207 | 1.373 (7) |
C106—C107 | 1.374 (7) | C206—H206 | 0.999 (4) |
C106—H106 | 1.002 (5) | C207—C208 | 1.391 (6) |
C107—C108 | 1.379 (7) | C207—H207 | 1.003 (5) |
C107—H107 | 0.998 (4) | C208—C213 | 1.387 (6) |
C108—C113 | 1.389 (5) | C208—H208 | 1.007 (4) |
C108—H108 | 1.006 (4) | C209—C210 | 1.515 (5) |
C109—C110 | 1.534 (5) | C209—C213 | 1.520 (5) |
C109—C113 | 1.525 (6) | C209—C214 | 1.546 (5) |
C109—C114 | 1.539 (6) | C209—C220 | 1.551 (5) |
C109—C120 | 1.544 (5) | C210—C211 | 1.399 (5) |
C110—C111 | 1.383 (5) | C211—C212 | 1.453 (5) |
C111—C112 | 1.468 (5) | C212—C213 | 1.395 (5) |
C112—C113 | 1.398 (6) | C214—C215 | 1.530 (5) |
C114—C115 | 1.522 (5) | C214—H214a | 1.003 (3) |
C114—H114a | 0.996 (3) | C214—H214b | 0.998 (4) |
C114—H114b | 0.999 (4) | C215—C216 | 1.521 (5) |
C115—C116 | 1.510 (6) | C215—H215a | 0.997 (3) |
C115—H115a | 0.998 (4) | C215—H215b | 1.000 (4) |
C115—H115b | 0.994 (4) | C216—C217 | 1.518 (5) |
C116—C117 | 1.513 (6) | C216—H216a | 0.999 (4) |
C116—H116a | 1.002 (4) | C216—H216b | 1.000 (4) |
C116—H116b | 1.002 (5) | C217—C218 | 1.519 (6) |
C117—C118 | 1.508 (8) | C217—H217a | 0.996 (3) |
C117—H117a | 1.001 (4) | C217—H217b | 0.996 (4) |
C117—H117b | 0.996 (5) | C218—C219 | 1.520 (6) |
C118—C119 | 1.495 (8) | C218—H218a | 0.999 (4) |
C118—H118a | 1.016 (6) | C218—H218b | 1.000 (4) |
C118—H118b | 1.027 (6) | C219—H219a | 1.016 (4) |
C119—H119a | 0.994 (6) | C219—H219b | 1.005 (4) |
C119—H119b | 1.002 (7) | C219—H219c | 0.969 (4) |
C119—H119c | 1.011 (7) | C220—C221 | 1.520 (5) |
C120—C121 | 1.513 (6) | C220—H220a | 1.000 (4) |
C120—H120a | 1.002 (4) | C220—H220b | 0.998 (3) |
C120—H120b | 0.995 (3) | C221—C222 | 1.520 (5) |
C121—C122 | 1.526 (5) | C221—H221a | 0.999 (4) |
C121—H121a | 1.000 (4) | C221—H221b | 0.999 (4) |
C121—H121b | 0.998 (3) | C222—C223 | 1.517 (6) |
C122—C123 | 1.518 (6) | C222—H222a | 1.000 (4) |
C122—H122a | 0.997 (4) | C222—H222b | 1.000 (4) |
C122—H122b | 0.994 (3) | C223—C224 | 1.523 (5) |
C123—C124 | 1.524 (5) | C223—H223a | 0.998 (4) |
C123—H123a | 1.001 (4) | C223—H223b | 0.995 (4) |
C123—H123b | 0.996 (4) | C224—C225 | 1.512 (6) |
C124—C125 | 1.517 (6) | C224—H224a | 1.005 (4) |
C124—H124a | 1.002 (4) | C224—H224b | 1.003 (4) |
C124—H124b | 0.997 (4) | C225—H225a | 0.995 (4) |
C125—H125a | 1.004 (4) | C225—H225b | 0.991 (4) |
C125—H125b | 0.999 (4) | C225—H225c | 1.000 (4) |
C125—H125c | 0.999 (4) | ||
C102—C101—C110 | 120.4 (3) | C202—C201—C210 | 120.7 (3) |
C102—C101—H101 | 119.8 (3) | C202—C201—H201 | 119.8 (3) |
C110—C101—H101 | 119.8 (3) | C210—C201—H201 | 119.5 (3) |
C101—C102—C103 | 116.7 (3) | C102—C202—C201 | 121.3 (3) |
C101—C102—C202 | 121.6 (3) | C102—C202—C203 | 121.5 (3) |
C103—C102—C202 | 121.7 (3) | C201—C202—C203 | 117.2 (3) |
C102—C103—C104 | 122.6 (3) | C202—C203—C204 | 122.3 (3) |
C102—C103—H103 | 118.4 (4) | C202—C203—H203 | 119.3 (4) |
C104—C103—H103 | 119.0 (4) | C204—C203—H203 | 118.4 (3) |
C103—C104—C111 | 119.2 (4) | C203—C204—C211 | 120.0 (3) |
C103—C104—H104 | 120.2 (3) | C203—C204—H204 | 119.9 (4) |
C111—C104—H104 | 120.6 (4) | C211—C204—H204 | 120.1 (4) |
C106—C105—C112 | 118.3 (4) | C206—C205—C212 | 118.9 (4) |
C106—C105—H105 | 120.8 (4) | C206—C205—H205 | 120.1 (4) |
C112—C105—H105 | 120.8 (4) | C212—C205—H205 | 121.0 (4) |
C105—C106—C107 | 121.4 (4) | C205—C206—C207 | 120.9 (4) |
C105—C106—H106 | 118.5 (5) | C205—C206—H206 | 119.1 (5) |
C107—C106—H106 | 120.1 (4) | C207—C206—H206 | 119.9 (4) |
C106—C107—C108 | 120.4 (4) | C206—C207—C208 | 120.5 (4) |
C106—C107—H107 | 119.3 (5) | C206—C207—H207 | 119.6 (4) |
C108—C107—H107 | 120.3 (5) | C208—C207—H207 | 119.9 (5) |
C107—C108—C113 | 119.4 (4) | C207—C208—C213 | 119.1 (4) |
C107—C108—H108 | 120.8 (4) | C207—C208—H208 | 120.9 (4) |
C113—C108—H108 | 119.8 (4) | C213—C208—H208 | 120.0 (4) |
C110—C109—C113 | 100.6 (3) | C210—C209—C213 | 101.4 (3) |
C110—C109—C114 | 112.3 (3) | C210—C209—C214 | 112.1 (3) |
C110—C109—C120 | 111.0 (3) | C210—C209—C220 | 112.0 (3) |
C113—C109—C114 | 112.9 (3) | C213—C209—C214 | 111.7 (3) |
C113—C109—C120 | 111.6 (3) | C213—C209—C220 | 111.8 (3) |
C114—C109—C120 | 108.3 (3) | C214—C209—C220 | 107.8 (3) |
C101—C110—C109 | 127.6 (3) | C201—C210—C209 | 128.1 (3) |
C101—C110—C111 | 121.4 (3) | C201—C210—C211 | 121.0 (3) |
C109—C110—C111 | 110.9 (3) | C209—C210—C211 | 110.9 (3) |
C104—C111—C110 | 119.7 (3) | C204—C211—C210 | 118.8 (3) |
C104—C111—C112 | 131.1 (4) | C204—C211—C212 | 133.0 (3) |
C110—C111—C112 | 109.2 (3) | C210—C211—C212 | 108.2 (3) |
C105—C112—C111 | 131.6 (4) | C205—C212—C211 | 130.5 (4) |
C105—C112—C113 | 120.5 (3) | C205—C212—C213 | 120.4 (4) |
C111—C112—C113 | 108.0 (4) | C211—C212—C213 | 109.2 (3) |
C108—C113—C109 | 128.7 (4) | C208—C213—C209 | 129.5 (3) |
C108—C113—C112 | 120.0 (4) | C208—C213—C212 | 120.2 (3) |
C109—C113—C112 | 111.3 (3) | C209—C213—C212 | 110.3 (3) |
C109—C114—C115 | 116.3 (3) | C209—C214—C215 | 116.3 (3) |
C109—C114—H114a | 107.6 (3) | C209—C214—H214a | 107.1 (3) |
C109—C114—H114b | 107.0 (3) | C209—C214—H214b | 107.6 (3) |
C115—C114—H114a | 108.0 (3) | C215—C214—H214a | 108.1 (3) |
C115—C114—H114b | 108.0 (3) | C215—C214—H214b | 108.3 (3) |
H114a—C114—H114b | 109.9 (3) | H214a—C214—H214b | 109.4 (3) |
C114—C115—C116 | 113.0 (3) | C214—C215—C216 | 110.8 (3) |
C114—C115—H115a | 108.2 (4) | C214—C215—H215a | 108.8 (3) |
C114—C115—H115b | 108.3 (3) | C214—C215—H215b | 108.8 (3) |
C116—C115—H115a | 108.5 (4) | C216—C215—H215a | 109.5 (3) |
C116—C115—H115b | 108.7 (4) | C216—C215—H215b | 109.3 (3) |
H115a—C115—H115b | 110.2 (4) | H215a—C215—H215b | 109.7 (3) |
C115—C116—C117 | 113.8 (3) | C215—C216—C217 | 113.9 (3) |
C115—C116—H116a | 108.5 (4) | C215—C216—H216a | 108.2 (3) |
C115—C116—H116b | 108.7 (4) | C215—C216—H216b | 108.0 (3) |
C117—C116—H116a | 108.2 (4) | C217—C216—H216a | 108.6 (3) |
C117—C116—H116b | 108.5 (4) | C217—C216—H216b | 108.5 (3) |
H116a—C116—H116b | 109.2 (4) | H216a—C216—H216b | 109.6 (3) |
C116—C117—C118 | 114.0 (4) | C216—C217—C218 | 112.4 (3) |
C116—C117—H117a | 108.9 (4) | C216—C217—H217a | 108.9 (3) |
C116—C117—H117b | 109.2 (4) | C216—C217—H217b | 108.8 (3) |
C118—C117—H117a | 107.6 (4) | C218—C217—H217a | 108.3 (3) |
C118—C117—H117b | 107.4 (4) | C218—C217—H217b | 108.3 (3) |
H117a—C117—H117b | 109.7 (4) | H217a—C217—H217b | 110.1 (3) |
C117—C118—C119 | 114.7 (5) | C217—C218—C219 | 114.8 (3) |
C117—C118—H118a | 109.1 (5) | C217—C218—H218a | 108.8 (4) |
C117—C118—H118b | 108.6 (5) | C217—C218—H218b | 108.7 (4) |
C119—C118—H118a | 109.5 (5) | C219—C218—H218a | 107.5 (4) |
C119—C118—H118b | 108.5 (5) | C219—C218—H218b | 107.4 (4) |
H118a—C118—H118b | 106.1 (6) | H218a—C218—H218b | 109.5 (3) |
C118—C119—H119a | 109.2 (5) | C218—C219—H219a | 107.5 (4) |
C118—C119—H119b | 108.3 (5) | C218—C219—H219b | 108.0 (4) |
C118—C119—H119c | 113.6 (6) | C218—C219—H219c | 110.2 (3) |
H119a—C119—H119b | 109.7 (7) | H219a—C219—H219b | 107.8 (3) |
H119a—C119—H119c | 108.3 (6) | H219a—C219—H219c | 111.1 (4) |
H119b—C119—H119c | 107.6 (6) | H219b—C219—H219c | 112.1 (4) |
C109—C120—C121 | 116.4 (3) | C209—C220—C221 | 115.8 (3) |
C109—C120—H120a | 107.2 (3) | C209—C220—H220a | 107.9 (3) |
C109—C120—H120b | 108.0 (3) | C209—C220—H220b | 107.8 (3) |
C121—C120—H120a | 107.5 (3) | C221—C220—H220a | 107.8 (3) |
C121—C120—H120b | 107.9 (3) | C221—C220—H220b | 107.9 (3) |
H120a—C120—H120b | 109.8 (3) | H220a—C220—H220b | 109.7 (3) |
C120—C121—C122 | 112.6 (3) | C220—C221—C222 | 111.5 (3) |
C120—C121—H121a | 108.3 (3) | C220—C221—H221a | 108.7 (3) |
C120—C121—H121b | 108.6 (3) | C220—C221—H221b | 108.8 (3) |
C122—C121—H121a | 108.7 (3) | C222—C221—H221a | 109.1 (3) |
C122—C121—H121b | 109.0 (3) | C222—C221—H221b | 109.0 (3) |
H121a—C121—H121b | 109.7 (3) | H221a—C221—H221b | 109.7 (3) |
C121—C122—C123 | 113.7 (3) | C221—C222—C223 | 114.4 (3) |
C121—C122—H122a | 108.0 (3) | C221—C222—H222a | 107.9 (3) |
C121—C122—H122b | 108.2 (3) | C221—C222—H222b | 107.9 (3) |
C123—C122—H122a | 108.2 (3) | C223—C222—H222a | 108.5 (3) |
C123—C122—H122b | 108.6 (3) | C223—C222—H222b | 108.6 (3) |
H122a—C122—H122b | 110.1 (3) | H222a—C222—H222b | 109.5 (3) |
C122—C123—C124 | 112.4 (3) | C222—C223—C224 | 112.0 (3) |
C122—C123—H123a | 108.2 (4) | C222—C223—H223a | 108.9 (3) |
C122—C123—H123b | 108.6 (3) | C222—C223—H223b | 109.1 (3) |
C124—C123—H123a | 108.7 (3) | C224—C223—H223a | 108.2 (3) |
C124—C123—H123b | 109.2 (4) | C224—C223—H223b | 108.5 (3) |
H123a—C123—H123b | 109.8 (4) | H223a—C223—H223b | 110.1 (3) |
C123—C124—C125 | 114.9 (3) | C223—C224—C225 | 115.3 (3) |
C123—C124—H124a | 107.9 (3) | C223—C224—H224a | 108.0 (4) |
C123—C124—H124b | 108.4 (4) | C223—C224—H224b | 108.3 (4) |
C125—C124—H124a | 107.7 (4) | C225—C224—H224a | 108.0 (4) |
C125—C124—H124b | 108.2 (4) | C225—C224—H224b | 108.3 (4) |
H124a—C124—H124b | 109.5 (4) | H224a—C224—H224b | 108.8 (4) |
C124—C125—H125a | 107.8 (4) | C224—C225—H225a | 107.2 (4) |
C124—C125—H125b | 108.3 (4) | C224—C225—H225b | 107.5 (4) |
C124—C125—H125c | 115.3 (4) | C224—C225—H225c | 114.4 (4) |
H125a—C125—H125b | 109.2 (4) | H225a—C225—H225b | 110.6 (4) |
H125a—C125—H125c | 107.9 (4) | H225a—C225—H225c | 108.5 (4) |
H125b—C125—H125c | 108.2 (4) | H225b—C225—H225c | 108.7 (4) |
Experimental details
Crystal data | |
Chemical formula | C50H66 |
Mr | 667.08 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 15.975 (2), 15.773 (2), 17.142 (2) |
β (°) | 100.51 (1) |
V (Å3) | 4246.9 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.06 |
Crystal size (mm) | 0.3 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [refl observed if Inet > .540 σ(Inet)] reflections | 7842, 7460, 4526 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.100, 0.039, 1.27 |
No. of reflections | 4526 |
No. of parameters | 452 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.35, −0.41 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, Xtal3.2 SORTRF ADDREF (Hall et al., 1992), Xtal3.2 GENTAN, Xtal3.2 CRYLSQ, Xtal3.2 ORTEP, Xtal3.2 BONDLA CIFIO.
Conducting polymers based on fluorene repeat units are well known to exhibit attractive luminescent properties allowing for instance the synthesis of blue light electroluminescent devices (Kraft et al., 1998; Stéphan & Vial, 1999). The corresponding polyfluorenes exhibit good thermal and chemical stability, high solubility and good solid-state fluorescence quantum yields. Nevertheless, in the solid state, the formation of film aggregates leads to altered spectrocopic properties (Klarner et al.,1998; Stéphan & Vial,1999). As a result, although the luminescence from isolated chain, such as in dilute solution, is blue, in the solid state, a broad and unstructured red-shifted band emission is observed due to the excimer emission. One way to avoid this excimer emission, which is an important problem, may be to investigate the use of oligomeric polyfluorene segments for which a well defined crystallization may occur. We report here the structure of the shortest oligomer which can be derived from fluorene, i.e. the dimer.
The main result concerning the molecular conformation is that the hexyl chains grafted at the 9 positions are on the same side of the rings, which is uncommon if compared to conducting polymers such as polypyrroles or polythiophenes in which the repeat units are head to foot (Handbook of Conducting Polymers, 1998). We note that one of the chains has a high thermal motion (Ueq for C119 = 0.19 Å2), the three others being normal. This can be explained by the environment, C119 having only one neighbour at less than 4.0 Å, while the others have four or five such neighbours. We tried to refine the structure from low-temperature (193 K) data but, although the displacement parameters are of course globally smaller, U(C119) remains much higher than the others and the refinement is not better than the room-temperature one.
The stacking of the molecules is such that ring planes are perpendicular in neighbouring molecules; there is no π-stacking between the planar conjugated fluorene segments. This result is in agreement with the photoluminescence measurements on dimer crystals, for which the shift leading to yellow instead of blue light is not observed.