The 9,9′-bifluorene-9,9′-diol molecules in the title compound, C
26H
18O
2·C
4H
8O
2, adopt a
gauche conformation stabilized by intramolecular O—H
O hydrogen bonds between hydroxyl groups. There are two formula units per asymmetric unit. The molecules are linked into one-dimensional chains by intermolecular O—H
O hydrogen bonds; ethyl acetate molecules are bound to these chains, also by O—H
O hydrogen bonds.
Supporting information
CCDC reference: 633606
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.120
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.830 0.976
Tmin(prime) and Tmax expected: 0.950 0.975
RR(prime) = 0.873
Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.87
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C53
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C57
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
Crystal data top
C26H18O2·C4H8O2 | Z = 4 |
Mr = 450.51 | F(000) = 952 |
Triclinic, P1 | Dx = 1.268 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5498 (18) Å | Cell parameters from 3729 reflections |
b = 12.464 (2) Å | θ = 2.3–26.3° |
c = 19.203 (3) Å | µ = 0.08 mm−1 |
α = 73.437 (2)° | T = 203 K |
β = 85.872 (2)° | Block, colourless |
γ = 77.195 (2)° | 0.60 × 0.50 × 0.30 mm |
V = 2359.9 (7) Å3 | |
Data collection top
Bruker SMART CCD diffractometer | 8153 independent reflections |
Radiation source: fine-focus sealed tube | 6351 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→12 |
Tmin = 0.830, Tmax = 0.976 | k = −14→14 |
11565 measured reflections | l = −17→22 |
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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.4614P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
8153 reflections | Δρmax = 0.27 e Å−3 |
614 parameters | Δρmin = −0.20 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: 0.0050 (7) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.56369 (11) | 1.07576 (10) | 0.28840 (6) | 0.0383 (3) | |
H1A | 0.6293 | 1.1019 | 0.2728 | 0.057* | |
O2 | 0.31156 (10) | 1.06629 (10) | 0.28241 (6) | 0.0351 (3) | |
H2A | 0.3425 | 1.1096 | 0.2989 | 0.053* | |
C1 | 0.64660 (16) | 0.91569 (15) | 0.23417 (10) | 0.0356 (4) | |
C2 | 0.72308 (17) | 0.83185 (16) | 0.28689 (11) | 0.0443 (5) | |
H2B | 0.7097 | 0.8285 | 0.3363 | 0.053* | |
C3 | 0.8205 (2) | 0.75239 (18) | 0.26494 (13) | 0.0561 (6) | |
H3A | 0.8743 | 0.6955 | 0.3001 | 0.067* | |
C4 | 0.8395 (2) | 0.75564 (18) | 0.19261 (14) | 0.0590 (6) | |
H4A | 0.9041 | 0.6996 | 0.1792 | 0.071* | |
C5 | 0.7651 (2) | 0.83999 (17) | 0.13998 (12) | 0.0513 (5) | |
H5A | 0.7782 | 0.8422 | 0.0907 | 0.062* | |
C6 | 0.67019 (17) | 0.92183 (15) | 0.16074 (10) | 0.0386 (4) | |
C7 | 0.58574 (17) | 1.02563 (15) | 0.11669 (10) | 0.0372 (4) | |
C8 | 0.5745 (2) | 1.06945 (17) | 0.04224 (11) | 0.0485 (5) | |
H8A | 0.6252 | 1.0307 | 0.0110 | 0.058* | |
C9 | 0.4872 (2) | 1.17119 (18) | 0.01452 (11) | 0.0545 (6) | |
H9A | 0.4777 | 1.2015 | −0.0360 | 0.065* | |
C10 | 0.4138 (2) | 1.22879 (17) | 0.06041 (11) | 0.0489 (5) | |
H10A | 0.3557 | 1.2984 | 0.0406 | 0.059* | |
C11 | 0.42460 (18) | 1.18552 (15) | 0.13509 (10) | 0.0402 (4) | |
H11A | 0.3744 | 1.2252 | 0.1660 | 0.048* | |
C12 | 0.51028 (16) | 1.08302 (14) | 0.16351 (9) | 0.0337 (4) | |
C13 | 0.53529 (16) | 1.01292 (14) | 0.24235 (9) | 0.0322 (4) | |
C14 | 0.36148 (16) | 0.90081 (15) | 0.23621 (10) | 0.0340 (4) | |
C15 | 0.30381 (18) | 0.93715 (17) | 0.16895 (10) | 0.0429 (5) | |
H15A | 0.2894 | 1.0147 | 0.1423 | 0.051* | |
C16 | 0.2676 (2) | 0.8570 (2) | 0.14152 (12) | 0.0588 (6) | |
H16A | 0.2277 | 0.8804 | 0.0959 | 0.071* | |
C17 | 0.2894 (3) | 0.7431 (2) | 0.18052 (14) | 0.0673 (7) | |
H17A | 0.2672 | 0.6896 | 0.1602 | 0.081* | |
C18 | 0.3431 (2) | 0.70647 (19) | 0.24872 (13) | 0.0585 (6) | |
H18A | 0.3555 | 0.6291 | 0.2755 | 0.070* | |
C19 | 0.37841 (18) | 0.78620 (16) | 0.27704 (11) | 0.0411 (5) | |
C20 | 0.42623 (18) | 0.77485 (16) | 0.34918 (11) | 0.0425 (5) | |
C21 | 0.4494 (2) | 0.68188 (19) | 0.41010 (13) | 0.0603 (6) | |
H21A | 0.4403 | 0.6094 | 0.4083 | 0.072* | |
C22 | 0.4861 (2) | 0.6973 (2) | 0.47364 (13) | 0.0699 (7) | |
H22A | 0.5026 | 0.6346 | 0.5153 | 0.084* | |
C23 | 0.4990 (2) | 0.8038 (2) | 0.47664 (12) | 0.0623 (6) | |
H23A | 0.5228 | 0.8131 | 0.5205 | 0.075* | |
C24 | 0.47703 (18) | 0.89762 (19) | 0.41535 (10) | 0.0460 (5) | |
H24A | 0.4867 | 0.9699 | 0.4172 | 0.055* | |
C25 | 0.44090 (16) | 0.88233 (16) | 0.35201 (10) | 0.0369 (4) | |
C26 | 0.41075 (16) | 0.96960 (14) | 0.27835 (9) | 0.0311 (4) | |
O3 | 1.04486 (11) | 0.13999 (10) | 0.27544 (7) | 0.0416 (3) | |
H3B | 1.1224 | 0.1183 | 0.2654 | 0.062* | |
O4 | 0.79207 (11) | 0.15330 (10) | 0.26577 (6) | 0.0369 (3) | |
H4B | 0.8456 | 0.1027 | 0.2932 | 0.055* | |
C27 | 0.98625 (16) | 0.18844 (15) | 0.14580 (10) | 0.0358 (4) | |
C28 | 0.94563 (18) | 0.09608 (16) | 0.13487 (11) | 0.0435 (5) | |
H28A | 0.9197 | 0.0404 | 0.1743 | 0.052* | |
C29 | 0.9441 (2) | 0.08770 (18) | 0.06446 (12) | 0.0519 (5) | |
H29A | 0.9151 | 0.0264 | 0.0561 | 0.062* | |
C30 | 0.9844 (2) | 0.16765 (18) | 0.00649 (12) | 0.0522 (5) | |
H30A | 0.9812 | 0.1607 | −0.0408 | 0.063* | |
C31 | 1.02932 (19) | 0.25793 (16) | 0.01690 (11) | 0.0444 (5) | |
H31A | 1.0590 | 0.3113 | −0.0225 | 0.053* | |
C32 | 1.02954 (17) | 0.26782 (15) | 0.08702 (10) | 0.0360 (4) | |
C33 | 1.06867 (16) | 0.35485 (14) | 0.11385 (9) | 0.0340 (4) | |
C34 | 1.12403 (18) | 0.44694 (16) | 0.07804 (10) | 0.0417 (5) | |
H34A | 1.1376 | 0.4648 | 0.0275 | 0.050* | |
C35 | 1.1589 (2) | 0.51210 (17) | 0.11785 (11) | 0.0488 (5) | |
H35A | 1.1969 | 0.5746 | 0.0942 | 0.059* | |
C36 | 1.1385 (2) | 0.48639 (18) | 0.19224 (11) | 0.0488 (5) | |
H36A | 1.1636 | 0.5312 | 0.2186 | 0.059* | |
C37 | 1.08148 (17) | 0.39501 (16) | 0.22854 (10) | 0.0411 (4) | |
H37A | 1.0676 | 0.3779 | 0.2791 | 0.049* | |
C38 | 1.04568 (16) | 0.32997 (14) | 0.18897 (9) | 0.0328 (4) | |
C39 | 0.98345 (16) | 0.22600 (14) | 0.21498 (9) | 0.0334 (4) | |
C40 | 0.82917 (16) | 0.31628 (15) | 0.30279 (9) | 0.0344 (4) | |
C41 | 0.87541 (18) | 0.27317 (18) | 0.37299 (10) | 0.0437 (5) | |
H41A | 0.9244 | 0.1980 | 0.3891 | 0.052* | |
C42 | 0.8479 (2) | 0.3432 (2) | 0.41929 (11) | 0.0548 (6) | |
H42A | 0.8790 | 0.3151 | 0.4671 | 0.066* | |
C43 | 0.7758 (2) | 0.4532 (2) | 0.39608 (12) | 0.0568 (6) | |
H43A | 0.7581 | 0.4991 | 0.4283 | 0.068* | |
C44 | 0.7289 (2) | 0.49684 (18) | 0.32593 (11) | 0.0478 (5) | |
H44A | 0.6796 | 0.5719 | 0.3102 | 0.057* | |
C45 | 0.75611 (17) | 0.42776 (15) | 0.27940 (9) | 0.0359 (4) | |
C46 | 0.70980 (16) | 0.44671 (15) | 0.20562 (9) | 0.0345 (4) | |
C47 | 0.62757 (19) | 0.54068 (16) | 0.16176 (11) | 0.0449 (5) | |
H47A | 0.6023 | 0.6097 | 0.1747 | 0.054* | |
C48 | 0.5839 (2) | 0.52989 (17) | 0.09849 (11) | 0.0509 (5) | |
H48A | 0.5274 | 0.5923 | 0.0683 | 0.061* | |
C49 | 0.6217 (2) | 0.42927 (18) | 0.07883 (11) | 0.0495 (5) | |
H49A | 0.5899 | 0.4239 | 0.0357 | 0.059* | |
C50 | 0.70597 (17) | 0.33581 (16) | 0.12166 (10) | 0.0404 (4) | |
H50A | 0.7318 | 0.2674 | 0.1080 | 0.049* | |
C51 | 0.75105 (16) | 0.34562 (14) | 0.18502 (9) | 0.0322 (4) | |
C52 | 0.84005 (16) | 0.25675 (14) | 0.24266 (9) | 0.0317 (4) | |
O5 | 0.31467 (13) | 0.22901 (11) | 0.36106 (7) | 0.0489 (3) | |
O6 | 0.29845 (13) | 0.40786 (11) | 0.36703 (7) | 0.0474 (3) | |
C53 | 0.4604 (2) | 0.3413 (2) | 0.29124 (14) | 0.0692 (7) | |
H53A | 0.4971 | 0.2741 | 0.2747 | 0.104* | |
H53B | 0.5269 | 0.3598 | 0.3154 | 0.104* | |
H53C | 0.4283 | 0.4054 | 0.2499 | 0.104* | |
C54 | 0.35137 (18) | 0.31763 (16) | 0.34291 (10) | 0.0415 (4) | |
C55 | 0.1890 (2) | 0.39850 (19) | 0.41710 (11) | 0.0518 (5) | |
H55A | 0.2193 | 0.3601 | 0.4669 | 0.062* | |
H55B | 0.1328 | 0.3546 | 0.4039 | 0.062* | |
C56 | 0.1171 (3) | 0.5178 (2) | 0.41126 (14) | 0.0780 (8) | |
H56A | 0.0426 | 0.5163 | 0.4440 | 0.117* | |
H56B | 0.0878 | 0.5546 | 0.3618 | 0.117* | |
H56C | 0.1741 | 0.5602 | 0.4243 | 0.117* | |
O7 | 0.92918 (16) | 0.77217 (13) | 0.43872 (8) | 0.0677 (5) | |
O8 | 0.88615 (13) | 0.96313 (11) | 0.39494 (7) | 0.0493 (4) | |
C57 | 1.0655 (2) | 0.85953 (19) | 0.34522 (13) | 0.0626 (6) | |
H57A | 1.1125 | 0.7818 | 0.3490 | 0.094* | |
H57B | 1.1235 | 0.9031 | 0.3560 | 0.094* | |
H57C | 1.0326 | 0.8951 | 0.2963 | 0.094* | |
C58 | 0.95503 (19) | 0.85738 (18) | 0.39784 (11) | 0.0475 (5) | |
C59 | 0.7814 (2) | 0.9715 (2) | 0.44822 (12) | 0.0564 (6) | |
H59A | 0.7407 | 0.9053 | 0.4570 | 0.068* | |
H59B | 0.7150 | 1.0407 | 0.4288 | 0.068* | |
C60 | 0.8303 (2) | 0.9755 (2) | 0.51783 (12) | 0.0675 (7) | |
H60A | 0.7587 | 0.9805 | 0.5522 | 0.101* | |
H60B | 0.8687 | 1.0421 | 0.5094 | 0.101* | |
H60C | 0.8954 | 0.9067 | 0.5373 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0309 (6) | 0.0450 (7) | 0.0461 (7) | −0.0147 (6) | 0.0027 (5) | −0.0195 (6) |
O2 | 0.0261 (6) | 0.0369 (7) | 0.0451 (7) | −0.0048 (5) | −0.0004 (5) | −0.0171 (5) |
C1 | 0.0260 (9) | 0.0320 (10) | 0.0486 (11) | −0.0084 (7) | 0.0034 (8) | −0.0102 (8) |
C2 | 0.0319 (10) | 0.0428 (11) | 0.0549 (12) | −0.0056 (9) | 0.0005 (9) | −0.0103 (9) |
C3 | 0.0368 (11) | 0.0427 (12) | 0.0783 (16) | 0.0012 (9) | −0.0018 (11) | −0.0072 (11) |
C4 | 0.0434 (12) | 0.0436 (12) | 0.0846 (17) | 0.0013 (10) | 0.0152 (12) | −0.0211 (12) |
C5 | 0.0470 (12) | 0.0440 (12) | 0.0634 (14) | −0.0078 (10) | 0.0166 (10) | −0.0208 (10) |
C6 | 0.0341 (10) | 0.0348 (10) | 0.0492 (11) | −0.0118 (8) | 0.0100 (8) | −0.0144 (8) |
C7 | 0.0373 (10) | 0.0341 (10) | 0.0423 (11) | −0.0127 (8) | 0.0058 (8) | −0.0114 (8) |
C8 | 0.0583 (13) | 0.0459 (12) | 0.0437 (12) | −0.0170 (10) | 0.0123 (10) | −0.0149 (9) |
C9 | 0.0704 (15) | 0.0507 (13) | 0.0391 (11) | −0.0166 (11) | 0.0005 (10) | −0.0046 (10) |
C10 | 0.0533 (13) | 0.0382 (11) | 0.0481 (12) | −0.0081 (9) | −0.0025 (10) | −0.0013 (9) |
C11 | 0.0373 (10) | 0.0336 (10) | 0.0475 (12) | −0.0078 (8) | 0.0041 (8) | −0.0089 (8) |
C12 | 0.0300 (9) | 0.0322 (9) | 0.0415 (10) | −0.0125 (8) | 0.0034 (8) | −0.0109 (8) |
C13 | 0.0277 (9) | 0.0311 (9) | 0.0396 (10) | −0.0072 (7) | 0.0009 (7) | −0.0122 (8) |
C14 | 0.0281 (9) | 0.0377 (10) | 0.0401 (10) | −0.0114 (8) | 0.0065 (8) | −0.0154 (8) |
C15 | 0.0425 (11) | 0.0483 (12) | 0.0433 (11) | −0.0193 (9) | 0.0035 (9) | −0.0147 (9) |
C16 | 0.0663 (15) | 0.0795 (17) | 0.0496 (13) | −0.0423 (13) | 0.0078 (11) | −0.0294 (12) |
C17 | 0.0878 (18) | 0.0690 (16) | 0.0717 (17) | −0.0484 (14) | 0.0218 (14) | −0.0423 (14) |
C18 | 0.0682 (15) | 0.0422 (12) | 0.0745 (16) | −0.0264 (11) | 0.0211 (13) | −0.0249 (11) |
C19 | 0.0352 (10) | 0.0356 (10) | 0.0538 (12) | −0.0109 (8) | 0.0112 (9) | −0.0147 (9) |
C20 | 0.0319 (10) | 0.0390 (11) | 0.0504 (12) | −0.0064 (8) | 0.0053 (9) | −0.0049 (9) |
C21 | 0.0511 (13) | 0.0433 (13) | 0.0734 (16) | −0.0084 (10) | 0.0018 (12) | 0.0028 (11) |
C22 | 0.0575 (15) | 0.0725 (18) | 0.0565 (15) | −0.0090 (13) | −0.0076 (12) | 0.0168 (12) |
C23 | 0.0487 (13) | 0.0831 (18) | 0.0428 (13) | −0.0114 (12) | −0.0088 (10) | 0.0019 (12) |
C24 | 0.0336 (10) | 0.0597 (13) | 0.0425 (11) | −0.0090 (9) | −0.0011 (9) | −0.0111 (10) |
C25 | 0.0247 (9) | 0.0426 (11) | 0.0394 (10) | −0.0063 (8) | 0.0028 (8) | −0.0065 (8) |
C26 | 0.0260 (9) | 0.0308 (9) | 0.0363 (10) | −0.0047 (7) | 0.0022 (7) | −0.0105 (7) |
O3 | 0.0253 (6) | 0.0413 (7) | 0.0477 (8) | −0.0035 (5) | −0.0031 (5) | 0.0021 (6) |
O4 | 0.0293 (6) | 0.0324 (7) | 0.0444 (7) | −0.0088 (5) | −0.0042 (5) | −0.0005 (5) |
C27 | 0.0270 (9) | 0.0306 (9) | 0.0488 (11) | −0.0034 (7) | 0.0024 (8) | −0.0119 (8) |
C28 | 0.0396 (11) | 0.0339 (10) | 0.0584 (13) | −0.0095 (8) | 0.0073 (9) | −0.0155 (9) |
C29 | 0.0513 (13) | 0.0463 (12) | 0.0695 (15) | −0.0162 (10) | 0.0097 (11) | −0.0323 (11) |
C30 | 0.0553 (13) | 0.0557 (13) | 0.0548 (13) | −0.0130 (11) | 0.0092 (10) | −0.0309 (11) |
C31 | 0.0472 (12) | 0.0410 (11) | 0.0469 (12) | −0.0106 (9) | 0.0080 (9) | −0.0161 (9) |
C32 | 0.0302 (9) | 0.0332 (10) | 0.0446 (11) | −0.0046 (8) | 0.0024 (8) | −0.0132 (8) |
C33 | 0.0284 (9) | 0.0317 (9) | 0.0399 (10) | −0.0044 (7) | −0.0023 (8) | −0.0080 (8) |
C34 | 0.0448 (11) | 0.0396 (11) | 0.0402 (11) | −0.0154 (9) | 0.0025 (9) | −0.0057 (8) |
C35 | 0.0546 (13) | 0.0421 (11) | 0.0526 (13) | −0.0261 (10) | −0.0015 (10) | −0.0053 (9) |
C36 | 0.0538 (13) | 0.0502 (12) | 0.0502 (13) | −0.0256 (10) | −0.0058 (10) | −0.0137 (10) |
C37 | 0.0387 (11) | 0.0481 (11) | 0.0386 (10) | −0.0155 (9) | −0.0054 (8) | −0.0094 (9) |
C38 | 0.0248 (9) | 0.0321 (9) | 0.0386 (10) | −0.0056 (7) | −0.0037 (7) | −0.0050 (8) |
C39 | 0.0278 (9) | 0.0315 (9) | 0.0387 (10) | −0.0066 (7) | −0.0028 (7) | −0.0054 (7) |
C40 | 0.0279 (9) | 0.0398 (10) | 0.0345 (10) | −0.0102 (8) | 0.0001 (7) | −0.0064 (8) |
C41 | 0.0381 (11) | 0.0501 (12) | 0.0382 (11) | −0.0076 (9) | −0.0049 (8) | −0.0051 (9) |
C42 | 0.0562 (13) | 0.0728 (16) | 0.0368 (11) | −0.0150 (12) | −0.0045 (10) | −0.0154 (11) |
C43 | 0.0607 (14) | 0.0680 (15) | 0.0512 (13) | −0.0159 (12) | 0.0014 (11) | −0.0301 (11) |
C44 | 0.0476 (12) | 0.0445 (12) | 0.0543 (13) | −0.0090 (9) | 0.0007 (10) | −0.0191 (10) |
C45 | 0.0310 (9) | 0.0379 (10) | 0.0394 (10) | −0.0102 (8) | 0.0001 (8) | −0.0096 (8) |
C46 | 0.0294 (9) | 0.0342 (10) | 0.0374 (10) | −0.0079 (8) | 0.0006 (7) | −0.0053 (8) |
C47 | 0.0429 (11) | 0.0326 (10) | 0.0527 (12) | −0.0045 (8) | −0.0022 (9) | −0.0035 (9) |
C48 | 0.0507 (13) | 0.0422 (12) | 0.0479 (12) | −0.0037 (10) | −0.0158 (10) | 0.0055 (9) |
C49 | 0.0506 (12) | 0.0532 (13) | 0.0400 (11) | −0.0080 (10) | −0.0154 (9) | −0.0038 (9) |
C50 | 0.0380 (11) | 0.0415 (11) | 0.0409 (11) | −0.0067 (8) | −0.0056 (8) | −0.0101 (8) |
C51 | 0.0254 (9) | 0.0346 (10) | 0.0340 (9) | −0.0079 (7) | −0.0006 (7) | −0.0040 (7) |
C52 | 0.0276 (9) | 0.0293 (9) | 0.0357 (10) | −0.0070 (7) | −0.0031 (7) | −0.0033 (7) |
O5 | 0.0525 (8) | 0.0418 (8) | 0.0565 (9) | −0.0170 (7) | 0.0058 (7) | −0.0159 (7) |
O6 | 0.0490 (8) | 0.0397 (8) | 0.0559 (8) | −0.0125 (6) | 0.0123 (7) | −0.0176 (6) |
C53 | 0.0596 (15) | 0.0498 (13) | 0.1008 (19) | −0.0197 (11) | 0.0360 (14) | −0.0274 (13) |
C54 | 0.0404 (11) | 0.0369 (11) | 0.0473 (11) | −0.0077 (9) | −0.0027 (9) | −0.0118 (9) |
C55 | 0.0509 (12) | 0.0613 (14) | 0.0441 (12) | −0.0144 (11) | 0.0101 (10) | −0.0168 (10) |
C56 | 0.0753 (18) | 0.0729 (18) | 0.0815 (18) | −0.0006 (14) | 0.0213 (14) | −0.0313 (14) |
O7 | 0.0709 (11) | 0.0507 (9) | 0.0675 (10) | −0.0142 (8) | 0.0093 (8) | 0.0045 (8) |
O8 | 0.0436 (8) | 0.0462 (8) | 0.0498 (8) | −0.0055 (6) | 0.0054 (6) | −0.0046 (6) |
C57 | 0.0597 (14) | 0.0500 (13) | 0.0719 (15) | −0.0083 (11) | 0.0177 (12) | −0.0138 (11) |
C58 | 0.0425 (11) | 0.0458 (12) | 0.0472 (12) | −0.0093 (10) | −0.0039 (9) | −0.0008 (10) |
C59 | 0.0347 (11) | 0.0646 (14) | 0.0613 (14) | −0.0067 (10) | 0.0052 (10) | −0.0082 (11) |
C60 | 0.0494 (13) | 0.0923 (19) | 0.0548 (14) | −0.0117 (13) | 0.0110 (11) | −0.0160 (13) |
Geometric parameters (Å, º) top
O1—C13 | 1.422 (2) | C31—C32 | 1.387 (3) |
O1—H1A | 0.830 | C31—H31A | 0.940 |
O2—C26 | 1.4270 (19) | C32—C33 | 1.470 (2) |
O2—H2A | 0.830 | C33—C34 | 1.386 (2) |
C1—C2 | 1.382 (3) | C33—C38 | 1.401 (2) |
C1—C6 | 1.397 (3) | C34—C35 | 1.381 (3) |
C1—C13 | 1.524 (2) | C34—H34A | 0.940 |
C2—C3 | 1.393 (3) | C35—C36 | 1.384 (3) |
C2—H2B | 0.940 | C35—H35A | 0.940 |
C3—C4 | 1.379 (3) | C36—C37 | 1.392 (3) |
C3—H3A | 0.940 | C36—H36A | 0.940 |
C4—C5 | 1.373 (3) | C37—C38 | 1.380 (2) |
C4—H4A | 0.940 | C37—H37A | 0.940 |
C5—C6 | 1.387 (3) | C38—C39 | 1.523 (2) |
C5—H5A | 0.940 | C39—C52 | 1.569 (2) |
C6—C7 | 1.469 (3) | C40—C41 | 1.382 (3) |
C7—C8 | 1.381 (3) | C40—C45 | 1.395 (2) |
C7—C12 | 1.402 (2) | C40—C52 | 1.526 (2) |
C8—C9 | 1.381 (3) | C41—C42 | 1.389 (3) |
C8—H8A | 0.940 | C41—H41A | 0.940 |
C9—C10 | 1.381 (3) | C42—C43 | 1.376 (3) |
C9—H9A | 0.940 | C42—H42A | 0.940 |
C10—C11 | 1.384 (3) | C43—C44 | 1.383 (3) |
C10—H10A | 0.940 | C43—H43A | 0.940 |
C11—C12 | 1.382 (2) | C44—C45 | 1.384 (3) |
C11—H11A | 0.940 | C44—H44A | 0.940 |
C12—C13 | 1.525 (2) | C45—C46 | 1.470 (2) |
C13—C26 | 1.570 (2) | C46—C47 | 1.388 (2) |
C14—C15 | 1.379 (3) | C46—C51 | 1.396 (2) |
C14—C19 | 1.398 (3) | C47—C48 | 1.381 (3) |
C14—C26 | 1.521 (2) | C47—H47A | 0.940 |
C15—C16 | 1.386 (3) | C48—C49 | 1.379 (3) |
C15—H15A | 0.940 | C48—H48A | 0.940 |
C16—C17 | 1.379 (3) | C49—C50 | 1.387 (3) |
C16—H16A | 0.940 | C49—H49A | 0.940 |
C17—C18 | 1.377 (3) | C50—C51 | 1.384 (2) |
C17—H17A | 0.940 | C50—H50A | 0.940 |
C18—C19 | 1.387 (3) | C51—C52 | 1.524 (2) |
C18—H18A | 0.940 | O5—C54 | 1.201 (2) |
C19—C20 | 1.466 (3) | O6—C54 | 1.331 (2) |
C20—C21 | 1.383 (3) | O6—C55 | 1.452 (2) |
C20—C25 | 1.399 (3) | C53—C54 | 1.488 (3) |
C21—C22 | 1.383 (3) | C53—H53A | 0.970 |
C21—H21A | 0.940 | C53—H53B | 0.970 |
C22—C23 | 1.381 (4) | C53—H53C | 0.970 |
C22—H22A | 0.940 | C55—C56 | 1.488 (3) |
C23—C24 | 1.393 (3) | C55—H55A | 0.980 |
C23—H23A | 0.940 | C55—H55B | 0.980 |
C24—C25 | 1.375 (3) | C56—H56A | 0.970 |
C24—H24A | 0.940 | C56—H56B | 0.970 |
C25—C26 | 1.523 (2) | C56—H56C | 0.970 |
O3—C39 | 1.417 (2) | O7—C58 | 1.200 (2) |
O3—H3B | 0.830 | O8—C58 | 1.345 (2) |
O4—C52 | 1.431 (2) | O8—C59 | 1.458 (2) |
O4—H4B | 0.830 | C57—C58 | 1.486 (3) |
C27—C28 | 1.386 (3) | C57—H57A | 0.970 |
C27—C32 | 1.397 (2) | C57—H57B | 0.970 |
C27—C39 | 1.526 (3) | C57—H57C | 0.970 |
C28—C29 | 1.387 (3) | C59—C60 | 1.485 (3) |
C28—H28A | 0.940 | C59—H59A | 0.980 |
C29—C30 | 1.378 (3) | C59—H59B | 0.980 |
C29—H29A | 0.940 | C60—H60A | 0.970 |
C30—C31 | 1.382 (3) | C60—H60B | 0.970 |
C30—H30A | 0.940 | C60—H60C | 0.970 |
| | | |
C13—O1—H1A | 109.5 | C38—C33—C32 | 108.52 (15) |
C26—O2—H2A | 109.5 | C35—C34—C33 | 118.91 (17) |
C2—C1—C6 | 120.24 (17) | C35—C34—H34A | 120.5 |
C2—C1—C13 | 129.51 (17) | C33—C34—H34A | 120.5 |
C6—C1—C13 | 110.21 (15) | C34—C35—C36 | 120.68 (18) |
C1—C2—C3 | 118.31 (19) | C34—C35—H35A | 119.7 |
C1—C2—H2B | 120.8 | C36—C35—H35A | 119.7 |
C3—C2—H2B | 120.8 | C35—C36—C37 | 120.83 (18) |
C4—C3—C2 | 121.2 (2) | C35—C36—H36A | 119.6 |
C4—C3—H3A | 119.4 | C37—C36—H36A | 119.6 |
C2—C3—H3A | 119.4 | C38—C37—C36 | 118.77 (18) |
C5—C4—C3 | 120.60 (19) | C38—C37—H37A | 120.6 |
C5—C4—H4A | 119.7 | C36—C37—H37A | 120.6 |
C3—C4—H4A | 119.7 | C37—C38—C33 | 120.28 (16) |
C4—C5—C6 | 118.9 (2) | C37—C38—C39 | 129.34 (16) |
C4—C5—H5A | 120.5 | C33—C38—C39 | 110.35 (15) |
C6—C5—H5A | 120.5 | O3—C39—C38 | 114.66 (14) |
C5—C6—C1 | 120.60 (18) | O3—C39—C27 | 114.72 (14) |
C5—C6—C7 | 130.48 (18) | C38—C39—C27 | 101.70 (14) |
C1—C6—C7 | 108.85 (15) | O3—C39—C52 | 102.91 (13) |
C8—C7—C12 | 120.85 (17) | C38—C39—C52 | 112.63 (14) |
C8—C7—C6 | 130.60 (17) | C27—C39—C52 | 110.58 (14) |
C12—C7—C6 | 108.54 (16) | C41—C40—C45 | 120.35 (17) |
C9—C8—C7 | 118.77 (19) | C41—C40—C52 | 129.23 (17) |
C9—C8—H8A | 120.6 | C45—C40—C52 | 110.36 (15) |
C7—C8—H8A | 120.6 | C40—C41—C42 | 118.61 (19) |
C8—C9—C10 | 120.60 (19) | C40—C41—H41A | 120.7 |
C8—C9—H9A | 119.7 | C42—C41—H41A | 120.7 |
C10—C9—H9A | 119.7 | C43—C42—C41 | 120.92 (19) |
C9—C10—C11 | 121.00 (19) | C43—C42—H42A | 119.5 |
C9—C10—H10A | 119.5 | C41—C42—H42A | 119.5 |
C11—C10—H10A | 119.5 | C42—C43—C44 | 120.8 (2) |
C12—C11—C10 | 118.95 (18) | C42—C43—H43A | 119.6 |
C12—C11—H11A | 120.5 | C44—C43—H43A | 119.6 |
C10—C11—H11A | 120.5 | C43—C44—C45 | 118.65 (19) |
C11—C12—C7 | 119.82 (17) | C43—C44—H44A | 120.7 |
C11—C12—C13 | 129.94 (16) | C45—C44—H44A | 120.7 |
C7—C12—C13 | 110.17 (15) | C44—C45—C40 | 120.66 (17) |
O1—C13—C1 | 114.01 (14) | C44—C45—C46 | 130.49 (17) |
O1—C13—C12 | 114.18 (14) | C40—C45—C46 | 108.59 (15) |
C1—C13—C12 | 101.75 (14) | C47—C46—C51 | 120.93 (17) |
O1—C13—C26 | 103.46 (13) | C47—C46—C45 | 129.96 (17) |
C1—C13—C26 | 112.76 (14) | C51—C46—C45 | 108.80 (15) |
C12—C13—C26 | 111.02 (13) | C48—C47—C46 | 118.07 (18) |
C15—C14—C19 | 120.60 (17) | C48—C47—H47A | 121.0 |
C15—C14—C26 | 129.41 (16) | C46—C47—H47A | 121.0 |
C19—C14—C26 | 109.96 (16) | C49—C48—C47 | 121.19 (18) |
C14—C15—C16 | 118.61 (19) | C49—C48—H48A | 119.4 |
C14—C15—H15A | 120.7 | C47—C48—H48A | 119.4 |
C16—C15—H15A | 120.7 | C48—C49—C50 | 121.04 (19) |
C17—C16—C15 | 120.7 (2) | C48—C49—H49A | 119.5 |
C17—C16—H16A | 119.7 | C50—C49—H49A | 119.5 |
C15—C16—H16A | 119.7 | C51—C50—C49 | 118.39 (18) |
C18—C17—C16 | 121.2 (2) | C51—C50—H50A | 120.8 |
C18—C17—H17A | 119.4 | C49—C50—H50A | 120.8 |
C16—C17—H17A | 119.4 | C50—C51—C46 | 120.33 (16) |
C17—C18—C19 | 118.6 (2) | C50—C51—C52 | 129.47 (16) |
C17—C18—H18A | 120.7 | C46—C51—C52 | 110.13 (15) |
C19—C18—H18A | 120.7 | O4—C52—C51 | 109.92 (13) |
C18—C19—C14 | 120.2 (2) | O4—C52—C40 | 111.86 (13) |
C18—C19—C20 | 130.75 (19) | C51—C52—C40 | 101.65 (14) |
C14—C19—C20 | 108.88 (16) | O4—C52—C39 | 107.70 (13) |
C21—C20—C25 | 120.3 (2) | C51—C52—C39 | 113.07 (13) |
C21—C20—C19 | 131.1 (2) | C40—C52—C39 | 112.64 (14) |
C25—C20—C19 | 108.56 (16) | C54—O6—C55 | 117.79 (15) |
C22—C21—C20 | 118.9 (2) | C54—C53—H53A | 109.5 |
C22—C21—H21A | 120.5 | C54—C53—H53B | 109.5 |
C20—C21—H21A | 120.5 | H53A—C53—H53B | 109.5 |
C23—C22—C21 | 120.8 (2) | C54—C53—H53C | 109.5 |
C23—C22—H22A | 119.6 | H53A—C53—H53C | 109.5 |
C21—C22—H22A | 119.6 | H53B—C53—H53C | 109.5 |
C22—C23—C24 | 120.7 (2) | O5—C54—O6 | 123.63 (18) |
C22—C23—H23A | 119.7 | O5—C54—C53 | 125.03 (18) |
C24—C23—H23A | 119.7 | O6—C54—C53 | 111.34 (17) |
C25—C24—C23 | 118.7 (2) | O6—C55—C56 | 106.15 (17) |
C25—C24—H24A | 120.7 | O6—C55—H55A | 110.5 |
C23—C24—H24A | 120.7 | C56—C55—H55A | 110.5 |
C24—C25—C20 | 120.72 (17) | O6—C55—H55B | 110.5 |
C24—C25—C26 | 129.15 (17) | C56—C55—H55B | 110.5 |
C20—C25—C26 | 110.14 (16) | H55A—C55—H55B | 108.7 |
O2—C26—C14 | 109.70 (13) | C55—C56—H56A | 109.5 |
O2—C26—C25 | 112.71 (13) | C55—C56—H56B | 109.5 |
C14—C26—C25 | 101.93 (14) | H56A—C56—H56B | 109.5 |
O2—C26—C13 | 108.70 (13) | C55—C56—H56C | 109.5 |
C14—C26—C13 | 112.25 (13) | H56A—C56—H56C | 109.5 |
C25—C26—C13 | 111.48 (14) | H56B—C56—H56C | 109.5 |
C39—O3—H3B | 109.5 | C58—O8—C59 | 116.59 (15) |
C52—O4—H4B | 109.5 | C58—C57—H57A | 109.5 |
C28—C27—C32 | 120.04 (18) | C58—C57—H57B | 109.5 |
C28—C27—C39 | 129.53 (17) | H57A—C57—H57B | 109.5 |
C32—C27—C39 | 110.28 (15) | C58—C57—H57C | 109.5 |
C27—C28—C29 | 118.47 (18) | H57A—C57—H57C | 109.5 |
C27—C28—H28A | 120.8 | H57B—C57—H57C | 109.5 |
C29—C28—H28A | 120.8 | O7—C58—O8 | 123.14 (19) |
C30—C29—C28 | 121.18 (19) | O7—C58—C57 | 124.8 (2) |
C30—C29—H29A | 119.4 | O8—C58—C57 | 112.08 (17) |
C28—C29—H29A | 119.4 | O8—C59—C60 | 111.35 (17) |
C29—C30—C31 | 120.9 (2) | O8—C59—H59A | 109.4 |
C29—C30—H30A | 119.5 | C60—C59—H59A | 109.4 |
C31—C30—H30A | 119.5 | O8—C59—H59B | 109.4 |
C30—C31—C32 | 118.26 (18) | C60—C59—H59B | 109.4 |
C30—C31—H31A | 120.9 | H59A—C59—H59B | 108.0 |
C32—C31—H31A | 120.9 | C59—C60—H60A | 109.5 |
C31—C32—C27 | 121.06 (17) | C59—C60—H60B | 109.5 |
C31—C32—C33 | 130.17 (17) | H60A—C60—H60B | 109.5 |
C27—C32—C33 | 108.77 (16) | C59—C60—H60C | 109.5 |
C34—C33—C38 | 120.51 (17) | H60A—C60—H60C | 109.5 |
C34—C33—C32 | 130.93 (17) | H60B—C60—H60C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O4i | 0.83 | 1.94 | 2.7513 (16) | 164 |
O2—H2A···O1 | 0.83 | 2.28 | 2.7006 (17) | 112 |
O2—H2A···O5i | 0.83 | 2.12 | 2.8597 (18) | 148 |
O3—H3B···O2ii | 0.83 | 1.98 | 2.7598 (16) | 157 |
O4—H4B···O3 | 0.83 | 2.23 | 2.6518 (17) | 111 |
O4—H4B···O8iii | 0.83 | 2.21 | 2.9521 (17) | 149 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y−1, z; (iii) x, y−1, z. |