6,13-Dihydropentacene and pentacene cocrystallize in a ratio of 2:1, i.e. C22H16·0.5C22H14, during vapour transport of commercial pentacene in a gas flow. The crystal structure is monoclinic, space group P21/n, and contains one dihydropentacene molecule and half a pentacene molecule in the asymmetric unit.
Supporting information
CCDC reference: 200763
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.013 Å
- R factor = 0.064
- wR factor = 0.151
- Data-to-parameter ratio = 6.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
THETM_01 Alert A The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.4812
Alert Level B:
REFNR_01 Alert B Ratio of reflections to parameters is < 8 for a
centrosymmetric structure
sine(theta)/lambda 0.4812
Proportion of unique data used 1.0000
Ratio reflections to parameters 6.6923
Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10
Rint given 0.123
1 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: CAD4-UNIX Software (Enraf-Nonius, 1994); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO (Meetsma, 2002) and PLATON (Spek, 1994); software used to prepare material for publication: PLATON (Spek, 1990).
6,13-dihydropentacene?
top
Crystal data top
C22H16·0.5C22H14 | F(000) = 884 |
Mr = 419.51 | Unit cell parameters (Duisenberg, 1992) and orientation matrix were determined
from a least-squares treatment of SET4 (de Boer & Duisenberg, 1984)setting.
Reduced cell calculations did not indicate any higher metric lattice symmetry
and examination of the final atomic coordinates of the structure did not yield
extra symmetry elements (Spek, 1988; Le Page 1987, 1988) |
Monoclinic, P21/n | Dx = 1.293 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 6.163 (4) Å | Cell parameters from 23 reflections |
b = 21.801 (5) Å | θ = 6.3–11.5° |
c = 16.069 (3) Å | µ = 0.07 mm−1 |
β = 93.73 (3)° | T = 293 K |
V = 2154.5 (15) Å3 | Needle, red |
Z = 4 | 0.32 × 0.07 × 0.05 mm |
Data collection top
Enraf Nonius CAD-4F diffractometer | Rint = 0.123 |
Radiation source: fine focus sealed Philips Mo tube | θmax = 20.0°, θmin = 1.6° |
Perpendicular mounted graphite monochromator | h = 0→5 |
ω/2θ scans | k = −20→20 |
4504 measured reflections | l = −15→15 |
2001 independent reflections | 2 standard reflections every 180 min |
770 reflections with I > 2σ(I) | intensity decay: <0.1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0453P)2] where P = (Fo2 + 2Fc2)/3 |
2001 reflections | (Δ/σ)max = 0.001 |
299 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C12 | 0.6148 (13) | 0.2396 (3) | 0.1595 (5) | 0.042 (3) | |
C13 | 0.5423 (15) | 0.2084 (3) | 0.0811 (5) | 0.040 (4) | |
C14 | 0.6607 (13) | 0.2110 (3) | 0.0113 (5) | 0.042 (3) | |
C15 | 0.5839 (16) | 0.1850 (4) | −0.0667 (5) | 0.041 (4) | |
C16 | 0.7019 (14) | 0.1905 (3) | −0.1390 (6) | 0.051 (4) | |
C17 | 0.6199 (16) | 0.1679 (4) | −0.2125 (6) | 0.057 (4) | |
C18 | 0.4163 (17) | 0.1381 (4) | −0.2184 (6) | 0.056 (4) | |
C19 | 0.3012 (14) | 0.1318 (4) | −0.1489 (6) | 0.053 (4) | |
C20 | 0.3785 (16) | 0.1565 (4) | −0.0709 (5) | 0.042 (4) | |
C21 | 0.2613 (13) | 0.1523 (4) | 0.0011 (5) | 0.044 (4) | |
C22 | 0.3401 (15) | 0.1781 (4) | 0.0738 (5) | 0.041 (3) | |
C23 | 0.2048 (12) | 0.1792 (4) | 0.1499 (5) | 0.051 (4) | |
C24 | 0.3385 (15) | 0.1760 (4) | 0.2316 (5) | 0.046 (4) | |
C25 | 0.2692 (13) | 0.1486 (4) | 0.3007 (5) | 0.044 (4) | |
C26 | 0.3918 (17) | 0.1486 (4) | 0.3781 (5) | 0.045 (4) | |
C27 | 0.3141 (16) | 0.1212 (4) | 0.4510 (6) | 0.061 (4) | |
C28 | 0.4406 (18) | 0.1223 (4) | 0.5247 (6) | 0.072 (5) | |
C29 | 0.6458 (18) | 0.1497 (4) | 0.5283 (6) | 0.070 (5) | |
C30 | 0.7201 (15) | 0.1766 (3) | 0.4591 (6) | 0.053 (4) | |
C31 | 0.5968 (15) | 0.1777 (4) | 0.3824 (5) | 0.042 (4) | |
C32 | 0.6676 (14) | 0.2049 (3) | 0.3096 (6) | 0.047 (4) | |
C33 | 0.5451 (14) | 0.2056 (4) | 0.2362 (5) | 0.041 (4) | |
C1 | −0.2130 (15) | 0.0286 (4) | −0.0147 (5) | 0.058 (4) | |
C2 | −0.1197 (15) | 0.0188 (4) | 0.0683 (6) | 0.043 (4) | |
C3 | −0.2363 (15) | 0.0361 (4) | 0.1381 (6) | 0.055 (4) | |
C4 | −0.1613 (16) | 0.0219 (4) | 0.2206 (6) | 0.048 (4) | |
C5 | −0.2805 (15) | 0.0332 (4) | 0.2906 (6) | 0.060 (4) | |
C6 | −0.2056 (19) | 0.0151 (4) | 0.3678 (6) | 0.073 (5) | |
C7 | −0.0065 (19) | −0.0142 (4) | 0.3821 (6) | 0.068 (5) | |
C8 | 0.1218 (16) | −0.0250 (4) | 0.3167 (6) | 0.060 (4) | |
C9 | 0.0474 (16) | −0.0075 (4) | 0.2343 (6) | 0.046 (4) | |
C10 | 0.1707 (15) | −0.0181 (4) | 0.1646 (6) | 0.059 (4) | |
C11 | −0.0912 (15) | 0.0092 (4) | −0.0831 (6) | 0.044 (4) | |
H12 | 0.55368 | 0.28162 | 0.15905 | 0.0503* | |
H12' | 0.77527 | 0.24315 | 0.16277 | 0.0503* | |
H14 | 0.79829 | 0.23078 | 0.01519 | 0.0505* | |
H16 | 0.83962 | 0.21025 | −0.13567 | 0.0614* | |
H17 | 0.70001 | 0.17199 | −0.26079 | 0.0688* | |
H18 | 0.35913 | 0.12251 | −0.27050 | 0.0675* | |
H19 | 0.16662 | 0.11045 | −0.15304 | 0.0642* | |
H21 | 0.12613 | 0.13118 | −0.00113 | 0.0528* | |
H23 | 0.11720 | 0.21724 | 0.14864 | 0.0612* | |
H23' | 0.10277 | 0.14403 | 0.14647 | 0.0612* | |
H25 | 0.13226 | 0.12839 | 0.29690 | 0.0527* | |
H27 | 0.17514 | 0.10222 | 0.44862 | 0.0731* | |
H28 | 0.38819 | 0.10426 | 0.57338 | 0.0858* | |
H29 | 0.73374 | 0.14957 | 0.57913 | 0.0843* | |
H30 | 0.85972 | 0.19526 | 0.46284 | 0.0635* | |
H32 | 0.80718 | 0.22352 | 0.31180 | 0.0557* | |
H1 | −0.35145 | 0.04747 | −0.02408 | 0.0689* | |
H3 | −0.36896 | 0.05801 | 0.12885 | 0.0662* | |
H5 | −0.41617 | 0.05386 | 0.28363 | 0.0720* | |
H6 | −0.29179 | 0.02272 | 0.41365 | 0.0879* | |
H7 | 0.04097 | −0.02676 | 0.43691 | 0.0821* | |
H8 | 0.25974 | −0.04404 | 0.32649 | 0.0716* | |
H10 | 0.31608 | −0.03222 | 0.17422 | 0.0705* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C12 | 0.031 (6) | 0.042 (5) | 0.054 (6) | 0.000 (4) | 0.004 (5) | −0.007 (5) |
C13 | 0.035 (6) | 0.037 (6) | 0.049 (7) | 0.000 (5) | 0.003 (5) | 0.008 (5) |
C14 | 0.026 (6) | 0.034 (5) | 0.067 (7) | −0.007 (4) | 0.007 (6) | 0.011 (5) |
C15 | 0.048 (7) | 0.035 (6) | 0.042 (7) | 0.005 (5) | 0.010 (5) | −0.009 (5) |
C16 | 0.044 (6) | 0.040 (6) | 0.070 (7) | −0.001 (5) | 0.010 (6) | −0.006 (6) |
C17 | 0.060 (8) | 0.060 (7) | 0.053 (8) | 0.005 (6) | 0.010 (6) | −0.006 (6) |
C18 | 0.073 (8) | 0.045 (6) | 0.051 (7) | 0.006 (6) | 0.002 (6) | −0.002 (5) |
C19 | 0.046 (7) | 0.055 (7) | 0.058 (7) | −0.003 (5) | −0.005 (6) | −0.002 (6) |
C20 | 0.039 (7) | 0.041 (6) | 0.044 (8) | 0.004 (5) | −0.007 (5) | −0.002 (5) |
C21 | 0.025 (6) | 0.048 (6) | 0.059 (7) | −0.004 (5) | −0.002 (5) | 0.011 (5) |
C22 | 0.037 (6) | 0.041 (5) | 0.045 (7) | −0.004 (5) | −0.003 (5) | −0.001 (5) |
C23 | 0.027 (6) | 0.069 (6) | 0.057 (7) | −0.001 (5) | 0.001 (5) | −0.002 (5) |
C24 | 0.036 (7) | 0.055 (6) | 0.047 (7) | −0.003 (5) | 0.007 (5) | −0.001 (5) |
C25 | 0.019 (5) | 0.061 (7) | 0.053 (7) | −0.008 (5) | 0.007 (5) | −0.007 (5) |
C26 | 0.059 (8) | 0.035 (6) | 0.041 (7) | 0.008 (6) | 0.001 (6) | −0.004 (5) |
C27 | 0.064 (8) | 0.055 (6) | 0.064 (7) | −0.009 (6) | 0.005 (7) | 0.002 (6) |
C28 | 0.078 (9) | 0.080 (8) | 0.057 (8) | −0.013 (7) | 0.006 (6) | −0.001 (6) |
C29 | 0.089 (10) | 0.062 (7) | 0.057 (8) | −0.006 (6) | −0.017 (7) | 0.010 (6) |
C30 | 0.059 (7) | 0.041 (6) | 0.056 (7) | 0.005 (5) | −0.014 (6) | −0.006 (5) |
C31 | 0.031 (6) | 0.045 (6) | 0.049 (7) | −0.003 (5) | 0.002 (5) | −0.009 (5) |
C32 | 0.035 (6) | 0.043 (6) | 0.062 (7) | 0.003 (5) | 0.003 (6) | −0.012 (5) |
C33 | 0.032 (6) | 0.039 (6) | 0.050 (7) | −0.008 (5) | −0.002 (5) | −0.004 (5) |
C1 | 0.043 (7) | 0.093 (8) | 0.036 (7) | 0.016 (6) | −0.002 (6) | 0.023 (6) |
C2 | 0.029 (7) | 0.039 (6) | 0.062 (9) | −0.005 (5) | 0.010 (5) | 0.003 (5) |
C3 | 0.039 (7) | 0.063 (7) | 0.063 (8) | 0.002 (5) | −0.003 (6) | 0.011 (6) |
C4 | 0.047 (8) | 0.029 (6) | 0.067 (9) | −0.004 (5) | −0.003 (6) | −0.005 (5) |
C5 | 0.057 (7) | 0.063 (7) | 0.062 (8) | 0.001 (5) | 0.021 (7) | −0.018 (6) |
C6 | 0.081 (9) | 0.088 (9) | 0.051 (9) | 0.003 (7) | 0.009 (7) | −0.001 (6) |
C7 | 0.078 (9) | 0.067 (8) | 0.059 (8) | 0.015 (7) | −0.005 (7) | −0.009 (6) |
C8 | 0.060 (7) | 0.064 (7) | 0.053 (8) | 0.009 (6) | −0.015 (6) | −0.015 (6) |
C9 | 0.048 (7) | 0.038 (6) | 0.051 (8) | −0.009 (5) | −0.003 (6) | −0.001 (5) |
C10 | 0.027 (6) | 0.089 (8) | 0.061 (8) | 0.007 (5) | 0.012 (6) | 0.027 (6) |
C11 | 0.026 (7) | 0.052 (6) | 0.053 (8) | 0.003 (5) | 0.002 (6) | 0.013 (5) |
Geometric parameters (Å, º) top
C12—C13 | 1.475 (11) | C18—H18 | 0.9498 |
C12—C33 | 1.524 (11) | C19—H19 | 0.9496 |
C13—C14 | 1.378 (12) | C21—H21 | 0.9505 |
C13—C22 | 1.409 (13) | C23—H23 | 0.9890 |
C14—C15 | 1.428 (11) | C23—H23' | 0.9909 |
C15—C16 | 1.415 (13) | C25—H25 | 0.9505 |
C15—C20 | 1.408 (14) | C27—H27 | 0.9497 |
C16—C17 | 1.347 (13) | C28—H28 | 0.9507 |
C17—C18 | 1.411 (14) | C29—H29 | 0.9504 |
C18—C19 | 1.368 (14) | C30—H30 | 0.9502 |
C19—C20 | 1.418 (13) | C32—H32 | 0.9498 |
C20—C21 | 1.406 (12) | C1—C2 | 1.434 (13) |
C21—C22 | 1.358 (12) | C1—C11 | 1.434 (13) |
C22—C23 | 1.524 (12) | C2—C3 | 1.422 (13) |
C23—C24 | 1.506 (12) | C2—C11i | 1.442 (13) |
C24—C25 | 1.354 (12) | C3—C4 | 1.410 (14) |
C24—C33 | 1.425 (13) | C4—C5 | 1.405 (14) |
C25—C26 | 1.413 (12) | C4—C9 | 1.441 (14) |
C26—C27 | 1.425 (13) | C5—C6 | 1.354 (14) |
C26—C31 | 1.411 (14) | C6—C7 | 1.389 (16) |
C27—C28 | 1.375 (14) | C7—C8 | 1.376 (14) |
C28—C29 | 1.396 (15) | C8—C9 | 1.425 (14) |
C29—C30 | 1.362 (13) | C9—C10 | 1.413 (14) |
C30—C31 | 1.405 (13) | C10—C11i | 1.382 (14) |
C31—C32 | 1.406 (12) | C1—H1 | 0.9504 |
C32—C33 | 1.358 (12) | C3—H3 | 0.9502 |
C12—H12 | 0.9903 | C5—H5 | 0.9499 |
C12—H12' | 0.9900 | C6—H6 | 0.9505 |
C14—H14 | 0.9497 | C7—H7 | 0.9501 |
C16—H16 | 0.9501 | C8—H8 | 0.9499 |
C17—H17 | 0.9506 | C10—H10 | 0.9505 |
| | | |
C5···C31ii | 3.580 (13) | H10···C18iii | 2.8983 |
C5···C26ii | 3.571 (13) | H10···C17iii | 3.0417 |
C10···C17iii | 3.577 (13) | H10···H1i | 2.4591 |
C17···C10iii | 3.577 (13) | H10···H8 | 2.5069 |
C26···C5iv | 3.571 (13) | H12···C23 | 3.0967 |
C31···C5iv | 3.580 (13) | H12'···H23iv | 2.2076 |
C1···H21 | 3.0591 | H12'···H32 | 2.4281 |
C4···H19i | 3.0823 | H12'···H14 | 2.4001 |
C6···H28v | 3.0115 | H12'···C23iv | 3.0109 |
C7···H27 | 2.9465 | H14···H12' | 2.4001 |
C7···H7v | 3.0629 | H14···H16 | 2.4944 |
C9···H19i | 2.8737 | H16···C32viii | 2.9176 |
C10···H19i | 2.8913 | H16···H14 | 2.4944 |
C11···H19 | 2.9820 | H16···C31viii | 2.9162 |
C12···H23 | 3.0989 | H16···C33viii | 3.0899 |
C13···H30vi | 3.0017 | H18···H28ix | 2.5578 |
C14···H30vi | 2.8347 | H19···C11 | 2.9820 |
C15···H1iv | 3.0955 | H19···C10i | 2.8913 |
C15···H30vi | 3.0057 | H19···H21 | 2.5109 |
C17···H32vi | 3.0933 | H19···C4i | 3.0823 |
C17···H10iii | 3.0417 | H19···C9i | 2.8737 |
C18···H10iii | 2.8983 | H21···H19 | 2.5109 |
C20···H1iv | 2.9704 | H21···H23' | 2.4019 |
C23···H12 | 3.0967 | H21···C1 | 3.0591 |
C23···H12'ii | 3.0109 | H23···C12 | 3.0989 |
C25···H5iv | 2.8584 | H23···H12'ii | 2.2076 |
C26···H5iv | 2.8644 | H23'···H25 | 2.4362 |
C31···H16vii | 2.9162 | H23'···H21 | 2.4019 |
C32···H16vii | 2.9176 | H25···H23' | 2.4362 |
C33···H16vii | 3.0899 | H25···H27 | 2.5011 |
H1···C15ii | 3.0955 | H27···C7 | 2.9465 |
H1···H10i | 2.4591 | H27···H25 | 2.5011 |
H1···C20ii | 2.9704 | H28···H18x | 2.5578 |
H1···H3 | 2.4775 | H28···C6v | 3.0115 |
H3···H5 | 2.5245 | H30···C15xi | 3.0057 |
H3···H1 | 2.4775 | H30···H32 | 2.5046 |
H5···C25ii | 2.8584 | H30···C14xi | 2.8347 |
H5···C26ii | 2.8644 | H30···C13xi | 3.0017 |
H5···H3 | 2.5245 | H32···H30 | 2.5046 |
H7···C7v | 3.0629 | H32···C17xi | 3.0933 |
H7···H7v | 2.4209 | H32···H12' | 2.4281 |
H8···H10 | 2.5069 | | |
| | | |
C13—C12—C33 | 112.4 (6) | C20—C21—H21 | 119.76 |
C12—C13—C14 | 121.9 (7) | C22—C21—H21 | 119.78 |
C12—C13—C22 | 120.3 (7) | C22—C23—H23 | 108.85 |
C14—C13—C22 | 117.6 (7) | C22—C23—H23' | 108.75 |
C13—C14—C15 | 122.3 (8) | C24—C23—H23 | 108.89 |
C14—C15—C16 | 121.9 (8) | C24—C23—H23' | 108.78 |
C14—C15—C20 | 117.6 (8) | H23—C23—H23' | 107.70 |
C16—C15—C20 | 120.4 (8) | C24—C25—H25 | 118.55 |
C15—C16—C17 | 120.3 (8) | C26—C25—H25 | 118.58 |
C16—C17—C18 | 120.6 (9) | C26—C27—H27 | 119.99 |
C17—C18—C19 | 119.8 (9) | C28—C27—H27 | 120.10 |
C18—C19—C20 | 121.4 (8) | C27—C28—H28 | 119.84 |
C15—C20—C19 | 117.3 (8) | C29—C28—H28 | 119.88 |
C15—C20—C21 | 119.8 (8) | C28—C29—H29 | 119.91 |
C19—C20—C21 | 122.8 (8) | C30—C29—H29 | 119.97 |
C20—C21—C22 | 120.5 (8) | C29—C30—H30 | 118.93 |
C13—C22—C21 | 122.1 (8) | C31—C30—H30 | 118.94 |
C13—C22—C23 | 116.9 (7) | C31—C32—H32 | 118.60 |
C21—C22—C23 | 120.9 (8) | C33—C32—H32 | 118.58 |
C22—C23—C24 | 113.7 (7) | C2—C1—C11 | 118.1 (8) |
C23—C24—C25 | 123.5 (8) | C1—C2—C3 | 120.1 (8) |
C23—C24—C33 | 117.4 (7) | C1—C2—C11i | 121.3 (8) |
C25—C24—C33 | 119.1 (8) | C3—C2—C11i | 118.6 (9) |
C24—C25—C26 | 122.9 (8) | C2—C3—C4 | 122.1 (8) |
C25—C26—C27 | 122.3 (9) | C3—C4—C5 | 123.9 (9) |
C25—C26—C31 | 118.0 (8) | C3—C4—C9 | 118.4 (9) |
C27—C26—C31 | 119.7 (8) | C5—C4—C9 | 117.6 (9) |
C26—C27—C28 | 119.9 (9) | C4—C5—C6 | 121.2 (9) |
C27—C28—C29 | 120.3 (9) | C5—C6—C7 | 122.0 (9) |
C28—C29—C30 | 120.1 (9) | C6—C7—C8 | 119.8 (9) |
C29—C30—C31 | 122.1 (9) | C7—C8—C9 | 119.9 (9) |
C26—C31—C30 | 117.8 (8) | C4—C9—C8 | 119.4 (9) |
C26—C31—C32 | 118.3 (8) | C4—C9—C10 | 118.2 (9) |
C30—C31—C32 | 123.9 (8) | C8—C9—C10 | 122.4 (9) |
C31—C32—C33 | 122.8 (8) | C9—C10—C11i | 123.5 (9) |
C12—C33—C24 | 118.4 (7) | C1—C11—C2i | 120.6 (8) |
C12—C33—C32 | 122.5 (8) | C1—C11—C10i | 120.9 (8) |
C24—C33—C32 | 119.0 (8) | C2i—C11—C10i | 118.4 (9) |
C13—C12—H12 | 109.05 | C2—C1—H1 | 120.91 |
C13—C12—H12' | 109.11 | C11—C1—H1 | 121.01 |
C33—C12—H12 | 109.19 | C2—C3—H3 | 118.94 |
C33—C12—H12' | 109.17 | C4—C3—H3 | 118.92 |
H12—C12—H12' | 107.83 | C4—C5—H5 | 119.40 |
C13—C14—H14 | 118.86 | C6—C5—H5 | 119.42 |
C15—C14—H14 | 118.79 | C5—C6—H6 | 119.00 |
C15—C16—H16 | 119.80 | C7—C6—H6 | 118.97 |
C17—C16—H16 | 119.86 | C6—C7—H7 | 120.08 |
C16—C17—H17 | 119.74 | C8—C7—H7 | 120.07 |
C18—C17—H17 | 119.69 | C7—C8—H8 | 120.06 |
C17—C18—H18 | 120.09 | C9—C8—H8 | 120.09 |
C19—C18—H18 | 120.08 | C9—C10—H10 | 118.29 |
C18—C19—H19 | 119.26 | C11i—C10—H10 | 118.16 |
C20—C19—H19 | 119.33 | | |
| | | |
C33—C12—C13—C14 | −148.4 (7) | C25—C26—C31—C30 | −178.8 (8) |
C33—C12—C13—C22 | 35.8 (10) | C25—C26—C31—C32 | −0.1 (12) |
C13—C12—C33—C24 | −36.4 (10) | C27—C26—C31—C30 | 2.0 (13) |
C13—C12—C33—C32 | 146.7 (8) | C27—C26—C31—C32 | −179.3 (8) |
C12—C13—C14—C15 | −175.0 (7) | C26—C27—C28—C29 | −0.5 (14) |
C22—C13—C14—C15 | 0.8 (11) | C27—C28—C29—C30 | 1.3 (14) |
C12—C13—C22—C21 | 175.6 (8) | C28—C29—C30—C31 | −0.4 (13) |
C12—C13—C22—C23 | −0.3 (11) | C29—C30—C31—C26 | −1.3 (12) |
C14—C13—C22—C21 | −0.3 (12) | C29—C30—C31—C32 | −179.9 (8) |
C14—C13—C22—C23 | −176.2 (7) | C26—C31—C32—C33 | 1.6 (12) |
C13—C14—C15—C16 | 176.9 (7) | C30—C31—C32—C33 | −179.7 (8) |
C13—C14—C15—C20 | 0.6 (12) | C31—C32—C33—C12 | 174.9 (7) |
C14—C15—C16—C17 | −176.9 (8) | C31—C32—C33—C24 | −1.9 (12) |
C20—C15—C16—C17 | −0.7 (12) | C11—C1—C2—C3 | −178.7 (8) |
C14—C15—C20—C19 | 178.8 (8) | C11—C1—C2—C11i | 0.6 (13) |
C14—C15—C20—C21 | −2.6 (13) | C2—C1—C11—C2i | −0.6 (13) |
C16—C15—C20—C19 | 2.5 (13) | C2—C1—C11—C10i | −179.1 (8) |
C16—C15—C20—C21 | −178.9 (8) | C1—C2—C3—C4 | 173.5 (8) |
C15—C16—C17—C18 | −0.4 (13) | C11i—C2—C3—C4 | −5.7 (13) |
C16—C17—C18—C19 | −0.3 (13) | C1—C2—C11i—C10 | −179.2 (8) |
C17—C18—C19—C20 | 2.2 (14) | C1—C2—C11i—C1i | −0.6 (13) |
C18—C19—C20—C15 | −3.2 (13) | C3—C2—C11i—C10 | 0.1 (13) |
C18—C19—C20—C21 | 178.2 (9) | C3—C2—C11i—C1i | 178.7 (8) |
C15—C20—C21—C22 | 3.1 (13) | C2—C3—C4—C5 | −174.0 (9) |
C19—C20—C21—C22 | −178.3 (8) | C2—C3—C4—C9 | 4.2 (13) |
C20—C21—C22—C13 | −1.7 (13) | C3—C4—C5—C6 | 175.9 (9) |
C20—C21—C22—C23 | 174.1 (8) | C9—C4—C5—C6 | −2.4 (13) |
C13—C22—C23—C24 | −35.6 (11) | C3—C4—C9—C8 | −176.9 (8) |
C21—C22—C23—C24 | 148.5 (8) | C3—C4—C9—C10 | 2.8 (13) |
C22—C23—C24—C25 | −147.9 (9) | C5—C4—C9—C8 | 1.4 (13) |
C22—C23—C24—C33 | 34.5 (11) | C5—C4—C9—C10 | −178.9 (8) |
C23—C24—C25—C26 | −176.7 (8) | C4—C5—C6—C7 | 1.4 (14) |
C33—C24—C25—C26 | 0.8 (13) | C5—C6—C7—C8 | 0.7 (14) |
C23—C24—C33—C12 | 1.4 (12) | C6—C7—C8—C9 | −1.6 (14) |
C23—C24—C33—C32 | 178.4 (8) | C7—C8—C9—C4 | 0.6 (13) |
C25—C24—C33—C12 | −176.3 (8) | C7—C8—C9—C10 | −179.2 (9) |
C25—C24—C33—C32 | 0.7 (13) | C4—C9—C10—C11i | −8.7 (13) |
C24—C25—C26—C27 | 178.0 (9) | C8—C9—C10—C11i | 171.0 (9) |
C24—C25—C26—C31 | −1.1 (13) | C9—C10—C11i—C2 | 7.2 (13) |
C25—C26—C27—C28 | 179.7 (9) | C9—C10—C11i—C1i | −171.4 (8) |
C31—C26—C27—C28 | −1.1 (13) | | |
Symmetry codes: (i) −x, −y, −z; (ii) x−1, y, z; (iii) −x+1, −y, −z; (iv) x+1, y, z; (v) −x, −y, −z+1; (vi) x−1/2, −y+1/2, z−1/2; (vii) x−1/2, −y+1/2, z+1/2; (viii) x+1/2, −y+1/2, z−1/2; (ix) x, y, z−1; (x) x, y, z+1; (xi) x+1/2, −y+1/2, z+1/2. |