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The title compound, C
20H
16O, has two molecules in the asymmetric unit, of nearly identical conformations, linked
via O—H
O—H, as well as O—H
π(fluorene) intermolecular hydrogen bonds. The 9-aryl and fluorene rings of both molecules deviate substantially from perpendicularity. Although the crystals melt sharply without molecular decomposition, the melt fails to recrystallize when cooled, even after a long period. Similar phenomena are observed with other crystalline 9-alkylphenyl-9-fluorenols that exhibit intermolecular π(arene) interactions.
Supporting information
CCDC reference: 227878
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.128
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor O1 - H1A ... ?
Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: TEXSAN, SHELXL97, and PLATON.
9-(
p-Methylpheny)-9-fluorenol
top
Crystal data top
C20H16O | F(000) = 1152 |
Mr = 272.33 | Dx = 1.211 Mg m−3 |
Monoclinic, P21/n | Melting point = 356–357 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71069 Å |
a = 12.621 (4) Å | Cell parameters from 25 reflections |
b = 10.778 (4) Å | θ = 16.7–19.6° |
c = 22.761 (7) Å | µ = 0.07 mm−1 |
β = 105.14 (3)° | T = 296 K |
V = 2988.7 (17) Å3 | Prism, colorless |
Z = 8 | 0.44 × 0.33 × 0.27 mm |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 1.9° |
Graphite monochromator | h = 0→15 |
ω scans | k = 0→12 |
5546 measured reflections | l = −27→26 |
5289 independent reflections | 3 standard reflections every 100 reflections |
2868 reflections with I > 2σ(I) | intensity decay: 1.7% |
Refinement top
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)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0591P)2 + 0.2677P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
5289 reflections | Δρmax = 0.20 e Å−3 |
384 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0139 (10) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.15663 (11) | 0.27897 (16) | 0.23708 (6) | 0.0579 (4) | |
C1 | 0.39983 (18) | 0.1875 (2) | 0.29893 (10) | 0.0561 (6) | |
C2 | 0.51209 (19) | 0.2072 (3) | 0.31012 (12) | 0.0669 (7) | |
C3 | 0.55786 (19) | 0.3181 (3) | 0.33309 (12) | 0.0679 (7) | |
C4 | 0.49421 (17) | 0.4132 (2) | 0.34616 (10) | 0.0583 (6) | |
C4A | 0.38209 (15) | 0.39415 (19) | 0.33535 (9) | 0.0441 (5) | |
C4B | 0.29436 (16) | 0.47599 (19) | 0.34378 (9) | 0.0443 (5) | |
C5 | 0.29805 (18) | 0.5958 (2) | 0.36651 (10) | 0.0546 (6) | |
C6 | 0.2009 (2) | 0.6522 (2) | 0.36826 (12) | 0.0643 (7) | |
C7 | 0.1023 (2) | 0.5915 (2) | 0.34843 (12) | 0.0653 (7) | |
C8 | 0.09757 (18) | 0.4707 (2) | 0.32614 (11) | 0.0564 (6) | |
C8A | 0.19458 (16) | 0.41380 (19) | 0.32438 (9) | 0.0440 (5) | |
C9 | 0.21163 (15) | 0.28457 (19) | 0.30139 (9) | 0.0434 (5) | |
C9A | 0.33591 (15) | 0.28200 (19) | 0.31146 (9) | 0.0437 (5) | |
C10 | 0.16866 (15) | 0.18069 (18) | 0.33403 (9) | 0.0421 (5) | |
C11 | 0.17879 (17) | 0.1880 (2) | 0.39614 (10) | 0.0523 (6) | |
C12 | 0.13763 (18) | 0.0959 (2) | 0.42615 (10) | 0.0560 (6) | |
C13 | 0.08608 (17) | −0.0077 (2) | 0.39588 (11) | 0.0520 (6) | |
C14 | 0.07945 (18) | −0.0159 (2) | 0.33464 (11) | 0.0571 (6) | |
C15 | 0.11948 (17) | 0.0763 (2) | 0.30383 (10) | 0.0535 (6) | |
C16 | 0.0356 (2) | −0.1042 (2) | 0.42818 (13) | 0.0735 (7) | |
H1A | 0.2018 | 0.2648 | 0.2178 | 0.087* | |
H1 | 0.3687 | 0.1123 | 0.2833 | 0.067* | |
H2 | 0.5567 | 0.1444 | 0.3019 | 0.080* | |
H3 | 0.6331 | 0.3296 | 0.3400 | 0.081* | |
H4 | 0.5258 | 0.4882 | 0.3618 | 0.070* | |
H5 | 0.3646 | 0.6371 | 0.3803 | 0.066* | |
H6 | 0.2021 | 0.7328 | 0.3831 | 0.077* | |
H7 | 0.0378 | 0.6315 | 0.3499 | 0.078* | |
H8 | 0.0308 | 0.4296 | 0.3128 | 0.068* | |
H11 | 0.2139 | 0.2560 | 0.4179 | 0.063* | |
H12 | 0.1448 | 0.1038 | 0.4677 | 0.067* | |
H14 | 0.0471 | −0.0857 | 0.3133 | 0.069* | |
H15 | 0.1131 | 0.0677 | 0.2624 | 0.064* | |
H16A | −0.0200 | −0.1488 | 0.3990 | 0.110* | |
H16B | 0.0034 | −0.0644 | 0.4570 | 0.110* | |
H16C | 0.0914 | −0.1610 | 0.4491 | 0.110* | |
O1' | 0.42586 (12) | 0.26159 (17) | 0.68952 (7) | 0.0666 (5) | |
C1' | 0.20343 (19) | 0.3640 (2) | 0.61393 (12) | 0.0640 (7) | |
C2' | 0.1450 (2) | 0.4574 (3) | 0.57798 (15) | 0.0799 (8) | |
C3' | 0.1748 (2) | 0.4989 (3) | 0.52771 (14) | 0.0828 (8) | |
C4' | 0.2636 (2) | 0.4488 (2) | 0.51157 (12) | 0.0722 (7) | |
C4A' | 0.32217 (17) | 0.3536 (2) | 0.54702 (10) | 0.0535 (6) | |
C4B' | 0.41777 (17) | 0.2820 (2) | 0.54136 (10) | 0.0546 (6) | |
C5' | 0.4768 (2) | 0.2845 (3) | 0.49777 (12) | 0.0751 (8) | |
C6' | 0.5625 (2) | 0.2037 (3) | 0.50289 (13) | 0.0822 (9) | |
C7' | 0.5899 (2) | 0.1191 (3) | 0.54968 (14) | 0.0752 (8) | |
C8' | 0.53172 (18) | 0.1157 (2) | 0.59397 (11) | 0.0614 (6) | |
C8A' | 0.44627 (16) | 0.1980 (2) | 0.58935 (10) | 0.0500 (5) | |
C9' | 0.36999 (16) | 0.2117 (2) | 0.63117 (9) | 0.0481 (5) | |
C9A' | 0.29254 (16) | 0.3128 (2) | 0.59822 (10) | 0.0499 (5) | |
C10' | 0.30938 (15) | 0.0933 (2) | 0.63824 (9) | 0.0459 (5) | |
C11' | 0.28187 (17) | 0.0063 (2) | 0.59222 (10) | 0.0516 (6) | |
C12' | 0.22254 (17) | −0.0986 (2) | 0.59843 (11) | 0.0565 (6) | |
C13' | 0.18875 (17) | −0.1210 (2) | 0.65008 (12) | 0.0570 (6) | |
C14' | 0.21602 (19) | −0.0344 (3) | 0.69595 (12) | 0.0675 (7) | |
C15' | 0.27508 (18) | 0.0705 (2) | 0.69030 (11) | 0.0618 (6) | |
C16' | 0.1243 (2) | −0.2355 (2) | 0.65612 (14) | 0.0801 (8) | |
H1A' | 0.4882 | 0.2330 | 0.7001 | 0.100* | |
H1' | 0.1831 | 0.3362 | 0.6481 | 0.077* | |
H2' | 0.0847 | 0.4924 | 0.5881 | 0.096* | |
H3' | 0.1345 | 0.5619 | 0.5041 | 0.099* | |
H4' | 0.2840 | 0.4780 | 0.4777 | 0.087* | |
H5' | 0.4585 | 0.3403 | 0.4655 | 0.090* | |
H6' | 0.6030 | 0.2060 | 0.4741 | 0.099* | |
H7' | 0.6474 | 0.0640 | 0.5518 | 0.090* | |
H8' | 0.5501 | 0.0592 | 0.6259 | 0.074* | |
H11' | 0.3035 | 0.0183 | 0.5566 | 0.062* | |
H12' | 0.2050 | −0.1555 | 0.5667 | 0.068* | |
H14' | 0.1942 | −0.0468 | 0.7315 | 0.081* | |
H15' | 0.2923 | 0.1272 | 0.7222 | 0.074* | |
H16'A | 0.0684 | −0.2489 | 0.6190 | 0.120* | |
H16'B | 0.0907 | −0.2249 | 0.6891 | 0.120* | |
H16'C | 0.1726 | −0.3058 | 0.6642 | 0.120* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0462 (8) | 0.0807 (11) | 0.0440 (8) | 0.0004 (8) | 0.0065 (7) | 0.0017 (8) |
C1 | 0.0509 (13) | 0.0572 (14) | 0.0588 (14) | 0.0058 (11) | 0.0119 (11) | 0.0021 (11) |
C2 | 0.0467 (14) | 0.0746 (18) | 0.0809 (18) | 0.0168 (13) | 0.0194 (12) | 0.0064 (14) |
C3 | 0.0362 (12) | 0.0801 (19) | 0.0843 (18) | 0.0037 (13) | 0.0100 (12) | 0.0153 (15) |
C4 | 0.0421 (12) | 0.0622 (15) | 0.0660 (15) | −0.0045 (11) | 0.0058 (11) | 0.0113 (12) |
C4A | 0.0383 (11) | 0.0485 (12) | 0.0437 (11) | −0.0012 (10) | 0.0075 (9) | 0.0091 (10) |
C4B | 0.0449 (11) | 0.0437 (12) | 0.0444 (12) | −0.0017 (10) | 0.0117 (9) | 0.0071 (10) |
C5 | 0.0582 (14) | 0.0466 (13) | 0.0595 (14) | −0.0080 (11) | 0.0161 (11) | 0.0028 (11) |
C6 | 0.0758 (17) | 0.0469 (14) | 0.0788 (17) | 0.0020 (13) | 0.0355 (14) | 0.0023 (12) |
C7 | 0.0614 (15) | 0.0542 (15) | 0.0902 (19) | 0.0120 (13) | 0.0376 (14) | 0.0072 (14) |
C8 | 0.0447 (12) | 0.0541 (14) | 0.0741 (16) | 0.0012 (11) | 0.0223 (11) | 0.0076 (12) |
C8A | 0.0431 (11) | 0.0449 (12) | 0.0462 (12) | 0.0011 (10) | 0.0153 (9) | 0.0076 (10) |
C9 | 0.0372 (10) | 0.0509 (13) | 0.0401 (11) | −0.0001 (10) | 0.0064 (9) | −0.0014 (10) |
C9A | 0.0395 (11) | 0.0502 (13) | 0.0412 (11) | 0.0044 (10) | 0.0103 (9) | 0.0067 (10) |
C10 | 0.0337 (10) | 0.0442 (12) | 0.0464 (12) | 0.0020 (9) | 0.0070 (9) | −0.0016 (10) |
C11 | 0.0519 (13) | 0.0534 (13) | 0.0473 (13) | −0.0108 (11) | 0.0050 (10) | −0.0059 (11) |
C12 | 0.0622 (14) | 0.0563 (14) | 0.0503 (13) | −0.0011 (12) | 0.0164 (11) | 0.0037 (12) |
C13 | 0.0464 (12) | 0.0432 (13) | 0.0677 (16) | 0.0030 (10) | 0.0169 (11) | 0.0026 (11) |
C14 | 0.0629 (15) | 0.0406 (13) | 0.0670 (16) | −0.0061 (11) | 0.0153 (12) | −0.0094 (11) |
C15 | 0.0590 (14) | 0.0494 (13) | 0.0529 (13) | −0.0032 (11) | 0.0158 (11) | −0.0102 (11) |
C16 | 0.0777 (17) | 0.0530 (15) | 0.097 (2) | −0.0023 (13) | 0.0354 (15) | 0.0105 (14) |
O1' | 0.0494 (9) | 0.0916 (13) | 0.0543 (10) | −0.0072 (9) | 0.0055 (7) | −0.0181 (9) |
C1' | 0.0550 (14) | 0.0643 (16) | 0.0751 (17) | 0.0006 (12) | 0.0211 (13) | −0.0021 (13) |
C2' | 0.0661 (17) | 0.0688 (18) | 0.104 (2) | 0.0110 (14) | 0.0204 (16) | −0.0039 (17) |
C3' | 0.0769 (19) | 0.0670 (19) | 0.096 (2) | 0.0160 (15) | 0.0070 (17) | 0.0078 (16) |
C4' | 0.0792 (18) | 0.0694 (17) | 0.0622 (16) | −0.0039 (15) | 0.0083 (14) | 0.0053 (14) |
C4A' | 0.0505 (13) | 0.0579 (14) | 0.0487 (13) | −0.0089 (11) | 0.0067 (10) | −0.0035 (11) |
C4B' | 0.0498 (13) | 0.0662 (15) | 0.0474 (13) | −0.0101 (11) | 0.0122 (10) | −0.0057 (12) |
C5' | 0.0769 (19) | 0.097 (2) | 0.0569 (15) | −0.0098 (16) | 0.0275 (14) | −0.0014 (15) |
C6' | 0.0748 (19) | 0.109 (2) | 0.0735 (19) | −0.0106 (18) | 0.0386 (15) | −0.0161 (18) |
C7' | 0.0549 (15) | 0.083 (2) | 0.093 (2) | −0.0063 (14) | 0.0280 (15) | −0.0274 (17) |
C8' | 0.0494 (13) | 0.0659 (15) | 0.0693 (16) | −0.0045 (12) | 0.0163 (12) | −0.0069 (13) |
C8A' | 0.0407 (11) | 0.0569 (14) | 0.0528 (13) | −0.0091 (10) | 0.0128 (10) | −0.0107 (11) |
C9' | 0.0396 (11) | 0.0592 (14) | 0.0438 (12) | −0.0061 (10) | 0.0077 (9) | −0.0070 (10) |
C9A' | 0.0422 (12) | 0.0536 (13) | 0.0523 (13) | −0.0082 (10) | 0.0098 (10) | −0.0090 (11) |
C10' | 0.0372 (11) | 0.0564 (13) | 0.0427 (11) | 0.0018 (10) | 0.0077 (9) | 0.0027 (11) |
C11' | 0.0492 (12) | 0.0579 (14) | 0.0480 (13) | −0.0057 (11) | 0.0131 (10) | 0.0031 (11) |
C12' | 0.0488 (13) | 0.0555 (14) | 0.0634 (15) | −0.0009 (11) | 0.0117 (11) | 0.0018 (12) |
C13' | 0.0391 (12) | 0.0585 (15) | 0.0736 (16) | 0.0063 (11) | 0.0150 (11) | 0.0214 (13) |
C14' | 0.0599 (15) | 0.0846 (19) | 0.0644 (16) | −0.0006 (14) | 0.0279 (13) | 0.0171 (15) |
C15' | 0.0590 (14) | 0.0756 (17) | 0.0529 (14) | −0.0028 (13) | 0.0184 (11) | −0.0011 (12) |
C16' | 0.0613 (16) | 0.0655 (17) | 0.119 (2) | 0.0066 (13) | 0.0326 (15) | 0.0268 (16) |
Geometric parameters (Å, º) top
O1—C9 | 1.448 (2) | C12—C13 | 1.382 (3) |
O1'—C9' | 1.435 (2) | C12'—C13' | 1.373 (3) |
C1—C9A | 1.375 (3) | C13—C14 | 1.377 (3) |
C1'—C9A' | 1.381 (3) | C13'—C14' | 1.375 (3) |
C1—C2 | 1.389 (3) | C13—C16 | 1.508 (3) |
C1'—C2' | 1.382 (4) | C13'—C16' | 1.505 (3) |
C2—C3 | 1.371 (4) | C14—C15 | 1.386 (3) |
C2'—C3' | 1.370 (4) | C14'—C15' | 1.378 (3) |
C3—C4 | 1.382 (3) | O1—H1A | 0.8200 |
C3'—C4' | 1.378 (4) | C1—H1 | 0.9300 |
C4—C4A | 1.387 (3) | C2—H2 | 0.9300 |
C4'—C4A' | 1.392 (3) | C3—H3 | 0.9300 |
C4A—C9A | 1.390 (3) | C4—H4 | 0.9300 |
C4A'—C9A' | 1.386 (3) | C5—H5 | 0.9300 |
C4A—C4B | 1.467 (3) | C6—H6 | 0.9300 |
C4A'—C4B' | 1.466 (3) | C7—H7 | 0.9300 |
C4B—C5 | 1.387 (3) | C8—H8 | 0.9300 |
C4B'—C5' | 1.388 (3) | C11—H11 | 0.9300 |
C4B—C8A | 1.393 (3) | C12—H12 | 0.9300 |
C4B'—C8A' | 1.392 (3) | C14—H14 | 0.9300 |
C5—C6 | 1.379 (3) | C15—H15 | 0.9300 |
C5'—C6' | 1.370 (4) | C16—H16A | 0.9600 |
C6—C7 | 1.374 (3) | C16—H16B | 0.9600 |
C6'—C7' | 1.376 (4) | C16—H16C | 0.9600 |
C7—C8 | 1.392 (3) | O1'—H1A' | 0.8200 |
C7'—C8' | 1.394 (3) | C1'—H1' | 0.9300 |
C8A—C8 | 1.380 (3) | C2'—H2' | 0.9300 |
C8A'—C8' | 1.379 (3) | C3'—H3' | 0.9300 |
C8A—C9 | 1.523 (3) | C4'—H4' | 0.9300 |
C8A'—C9' | 1.528 (3) | C5'—H5' | 0.9300 |
C9A—C9 | 1.525 (3) | C6'—H6' | 0.9300 |
C9'—C9A' | 1.523 (3) | C7'—H7' | 0.9300 |
C9—C10 | 1.520 (3) | C8'—H8' | 0.9300 |
C9'—C10' | 1.518 (3) | C11'—H11' | 0.9300 |
C10—C15 | 1.379 (3) | C12'—H12' | 0.9300 |
C10'—C15' | 1.385 (3) | C14'—H14' | 0.9300 |
C10—C11 | 1.388 (3) | C15'—H15' | 0.9300 |
C10'—C11' | 1.381 (3) | C16'—H16'A | 0.9600 |
C11—C12 | 1.381 (3) | C16'—H16'B | 0.9600 |
C11'—C12' | 1.383 (3) | C16'—H16'C | 0.9600 |
| | | |
C9A—C1—C2 | 118.3 (2) | C12'—C13'—C16' | 121.3 (2) |
C9A'—C1'—C2' | 118.9 (3) | C10—C15—C14 | 120.6 (2) |
C3—C2—C1 | 120.7 (2) | C14'—C15'—C10' | 121.5 (2) |
C3'—C2'—C1' | 120.8 (3) | C11—C12—C13 | 121.5 (2) |
C3—C4—C4A | 118.4 (2) | C13'—C12'—C11' | 121.9 (2) |
C3'—C4'—C4A' | 118.7 (3) | C9—O1—H1A | 109.5 |
C4—C4A—C9A | 120.2 (2) | C9A—C1—H1 | 120.8 |
C9A'—C4A'—C4' | 120.2 (2) | C2—C1—H1 | 120.8 |
C4—C4A—C4B | 131.1 (2) | C3—C2—H2 | 119.6 |
C4'—C4A'—C4B' | 131.4 (2) | C1—C2—H2 | 119.6 |
C9A—C4A—C4B | 108.70 (17) | C2—C3—H3 | 119.4 |
C9A'—C4A'—C4B' | 108.4 (2) | C4—C3—H3 | 119.4 |
C5—C4B—C8A | 120.4 (2) | C3—C4—H4 | 120.8 |
C5'—C4B'—C8A' | 119.8 (2) | C4A—C4—H4 | 120.8 |
C5—C4B—C4A | 130.96 (19) | C6—C5—H5 | 120.7 |
C5'—C4B'—C4A' | 131.3 (2) | C4B—C5—H5 | 120.7 |
C8A—C4B—C4A | 108.66 (18) | C7—C6—H6 | 119.5 |
C8A'—C4B'—C4A' | 108.88 (19) | C5—C6—H6 | 119.5 |
C6—C5—C4B | 118.6 (2) | C6—C7—H7 | 119.5 |
C6'—C5'—C4B' | 119.1 (3) | C8—C7—H7 | 119.5 |
C2—C3—C4 | 121.2 (2) | C8A—C8—H8 | 120.9 |
C2'—C3'—C4' | 121.0 (3) | C7—C8—H8 | 120.9 |
C7—C6—C5 | 121.1 (2) | C12—C11—H11 | 119.4 |
C5'—C6'—C7' | 121.4 (2) | C10—C11—H11 | 119.4 |
C6—C7—C8 | 120.9 (2) | C11—C12—H12 | 119.2 |
C6'—C7'—C8' | 120.3 (3) | C13—C12—H12 | 119.2 |
C8—C8A—C4B | 120.8 (2) | C13—C14—H14 | 118.9 |
C8'—C8A'—C4B' | 121.0 (2) | C15—C14—H14 | 118.9 |
C8—C8A—C9 | 128.54 (19) | C10—C15—H15 | 119.7 |
C8'—C8A'—C9' | 128.5 (2) | C14—C15—H15 | 119.7 |
C4B—C8A—C9 | 110.61 (17) | C13—C16—H16A | 109.5 |
C4B'—C8A'—C9' | 110.49 (19) | C13—C16—H16B | 109.5 |
C8A—C8—C7 | 118.2 (2) | H16A—C16—H16B | 109.5 |
C8A'—C8'—C7' | 118.5 (2) | C13—C16—H16C | 109.5 |
C1—C9A—C4A | 121.11 (19) | H16A—C16—H16C | 109.5 |
C1'—C9A'—C4A' | 120.5 (2) | H16B—C16—H16C | 109.5 |
C1—C9A—C9 | 128.2 (2) | C9'—O1'—H1A' | 109.5 |
C1'—C9A'—C9' | 128.3 (2) | C2'—C1'—H1' | 120.6 |
C4A—C9A—C9 | 110.66 (17) | C9A'—C1'—H1' | 120.6 |
C4A'—C9A'—C9' | 111.21 (19) | C3'—C2'—H2' | 119.6 |
O1—C9—C10 | 108.99 (16) | C2'—C3'—H3' | 119.5 |
O1'—C9'—C10' | 110.86 (17) | C4'—C3'—H3' | 119.5 |
O1—C9—C9A | 110.72 (16) | C1'—C2'—H2' | 119.6 |
O1'—C9'—C9A' | 106.55 (18) | C3'—C4'—H4' | 120.6 |
C10—C9—C9A | 113.41 (16) | C6'—C5'—H5' | 120.5 |
C10'—C9'—C9A' | 112.15 (16) | C4B'—C5'—H5' | 120.5 |
O1—C9—C8A | 108.18 (16) | C4A'—C4'—H4' | 120.6 |
O1'—C9'—C8A' | 112.06 (16) | C5'—C6'—H6' | 119.3 |
C10—C9—C8A | 113.92 (16) | C7'—C6'—H6' | 119.3 |
C10'—C9'—C8A' | 113.65 (17) | C6'—C7'—H7' | 119.9 |
C9A—C9—C8A | 101.36 (16) | C8'—C7'—H7' | 119.9 |
C9A'—C9'—C8A' | 100.98 (18) | C8A'—C8'—H8' | 120.8 |
C15—C10—C11 | 117.6 (2) | C7'—C8'—H8' | 120.8 |
C11'—C10'—C15' | 117.1 (2) | C10'—C11'—H11' | 119.6 |
C15—C10—C9 | 121.94 (19) | C12'—C11'—H11' | 119.6 |
C15'—C10'—C9' | 121.2 (2) | C13'—C12'—H12' | 119.0 |
C11—C10—C9 | 120.42 (18) | C11'—C12'—H12' | 119.0 |
C11'—C10'—C9' | 121.63 (18) | C15'—C14'—H14' | 119.3 |
C12—C11—C10 | 121.1 (2) | C13'—C14'—H14' | 119.3 |
C10'—C11'—C12' | 120.9 (2) | C14'—C15'—H15' | 119.2 |
C13—C14—C15 | 122.1 (2) | C10'—C15'—H15' | 119.2 |
C15'—C14'—C13' | 121.3 (2) | C13'—C16'—H16'A | 109.5 |
C14—C13—C12 | 116.9 (2) | C13'—C16'—H16'B | 109.5 |
C12'—C13'—C14' | 117.3 (2) | H16'A—C16'—H16'B | 109.5 |
C14—C13—C16 | 121.8 (2) | C13'—C16'—H16'C | 109.5 |
C14'—C13'—C16' | 121.4 (2) | H16'A—C16'—H16'C | 109.5 |
C12—C13—C16 | 121.2 (2) | H16'B—C16'—H16'C | 109.5 |
| | | |
C9A—C1—C2—C3 | 0.0 (4) | C4A—C9A—C9—O1 | 113.45 (19) |
C9A'—C1'—C2'—C3' | −0.2 (4) | O1'—C9'—C9A'—C4A' | 115.23 (19) |
C1—C2—C3—C4 | 0.4 (4) | C1—C9A—C9—C10 | 57.6 (3) |
C1'—C2'—C3'—C4' | 0.1 (4) | C10'—C9'—C9A'—C1' | 57.4 (3) |
C2—C3—C4—C4A | −0.1 (4) | C4A—C9A—C9—C10 | −123.67 (19) |
C2'—C3'—C4'—C4A' | 0.7 (4) | C10'—C9'—C9A'—C4A' | −123.29 (19) |
C3—C4—C4A—C9A | −0.5 (3) | C1—C9A—C9—C8A | −179.9 (2) |
C3'—C4'—C4A'—C9A' | −1.5 (4) | C8A'—C9'—C9A'—C1' | 178.8 (2) |
C3—C4—C4A—C4B | −179.3 (2) | C4A—C9A—C9—C8A | −1.1 (2) |
C3'—C4'—C4A'—C4B' | 179.3 (2) | C8A'—C9'—C9A'—C4A' | −1.9 (2) |
C4—C4A—C4B—C5 | −1.8 (4) | C8—C8A—C9—O1 | 62.7 (3) |
C4'—C4A'—C4B'—C5' | −2.4 (4) | C8'—C8A'—C9'—O1' | 69.9 (3) |
C9A—C4A—C4B—C5 | 179.3 (2) | C4B—C8A—C9—O1 | −115.70 (18) |
C9A'—C4A'—C4B'—C5' | 178.3 (2) | C4B'—C8A'—C9'—O1' | −111.3 (2) |
C4—C4A—C4B—C8A | 178.3 (2) | C8—C8A—C9—C10 | −58.7 (3) |
C4'—C4A'—C4B'—C8A' | 179.1 (2) | C8'—C8A'—C9'—C10' | −56.7 (3) |
C9A—C4A—C4B—C8A | −0.6 (2) | C4B—C8A—C9—C10 | 122.95 (18) |
C9A'—C4A'—C4B'—C8A' | −0.2 (2) | C4B'—C8A'—C9'—C10' | 122.1 (2) |
C8A—C4B—C5—C6 | −1.3 (3) | C8—C8A—C9—C9A | 179.1 (2) |
C8A'—C4B'—C5'—C6' | 0.1 (4) | C8'—C8A'—C9'—C9A' | −177.0 (2) |
C4A—C4B—C5—C6 | 178.8 (2) | C4B—C8A—C9—C9A | 0.8 (2) |
C4A'—C4B'—C5'—C6' | −178.3 (2) | C4B'—C8A'—C9'—C9A' | 1.8 (2) |
C4B—C5—C6—C7 | 0.5 (4) | O1—C9—C10—C15 | 21.9 (3) |
C4B'—C5'—C6'—C7' | 1.0 (4) | O1'—C9'—C10'—C15' | 25.4 (3) |
C5—C6—C7—C8 | 0.2 (4) | C9A—C9—C10—C15 | −101.9 (2) |
C5'—C6'—C7'—C8' | −1.3 (4) | C9A'—C9'—C10'—C15' | −93.5 (2) |
C5—C4B—C8A—C8 | 1.4 (3) | C8A—C9—C10—C15 | 142.78 (19) |
C5'—C4B'—C8A'—C8' | −0.8 (3) | C8A'—C9'—C10'—C15' | 152.7 (2) |
C4A—C4B—C8A—C8 | −178.67 (19) | O1—C9—C10—C11 | −158.64 (17) |
C4A'—C4B'—C8A'—C8' | 177.85 (19) | O1'—C9'—C10'—C11' | −157.41 (19) |
C5—C4B—C8A—C9 | 179.91 (18) | C9A—C9—C10—C11 | 77.5 (2) |
C5'—C4B'—C8A'—C9' | −179.8 (2) | C9A'—C9'—C10'—C11' | 83.6 (2) |
C4A—C4B—C8A—C9 | −0.2 (2) | C8A—C9—C10—C11 | −37.7 (3) |
C4A'—C4B'—C8A'—C9' | −1.1 (2) | C8A'—C9'—C10'—C11' | −30.1 (3) |
C4B—C8A—C8—C7 | −0.7 (3) | C15—C10—C11—C12 | −2.2 (3) |
C4B'—C8A'—C8'—C7' | 0.6 (3) | C15'—C10'—C11'—C12' | 0.1 (3) |
C9—C8A—C8—C7 | −178.9 (2) | C9—C10—C11—C12 | 178.29 (19) |
C9'—C8A'—C8'—C7' | 179.3 (2) | C9'—C10'—C11'—C12' | −177.20 (19) |
C6—C7—C8—C8A | −0.1 (4) | C10—C11—C12—C13 | 0.8 (3) |
C6'—C7'—C8'—C8A' | 0.5 (4) | C10'—C11'—C12'—C13' | −0.1 (3) |
C2—C1—C9A—C4A | −0.7 (3) | C11—C12—C13—C14 | 1.2 (3) |
C2'—C1'—C9A'—C4A' | −0.5 (3) | C11'—C12'—C13'—C14' | 0.2 (3) |
C2—C1—C9A—C9 | 177.9 (2) | C11—C12—C13—C16 | −176.5 (2) |
C2'—C1'—C9A'—C9' | 178.7 (2) | C11'—C12'—C13'—C16' | −180.0 (2) |
C4—C4A—C9A—C1 | 1.0 (3) | C12—C13—C14—C15 | −1.8 (3) |
C4'—C4A'—C9A'—C1' | 1.4 (3) | C12'—C13'—C14'—C15' | −0.1 (3) |
C4B—C4A—C9A—C1 | 179.97 (18) | C16—C13—C14—C15 | 175.8 (2) |
C4B'—C4A'—C9A'—C1' | −179.2 (2) | C16'—C13'—C14'—C15' | −180.0 (2) |
C4—C4A—C9A—C9 | −177.89 (18) | C11—C10—C15—C14 | 1.6 (3) |
C4'—C4A'—C9A'—C9' | −177.99 (19) | C11'—C10'—C15'—C14' | 0.0 (3) |
C4B—C4A—C9A—C9 | 1.1 (2) | C9—C10—C15—C14 | −178.91 (19) |
C4B'—C4A'—C9A'—C9' | 1.4 (2) | C9'—C10'—C15'—C14' | 177.2 (2) |
C1—C9A—C9—O1 | −65.3 (3) | C13—C14—C15—C10 | 0.4 (3) |
O1'—C9'—C9A'—C1' | −64.1 (3) | C13'—C14'—C15'—C10' | 0.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1′i—H1A′i···O1 | 0.82 | 2.08 | 2.863 (2) | 161 |
O1—H1A···C5ii | 0.82 | 2.65 | 3.239 (3) | 130 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1/2, y−1/2, −z+1/2. |
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