The title compound, C
36H
50O
3·C
2H
4O
2, crystallizes with acetic acid solvent molecules in a 1.1 stoichiometric molar ratio. The molecules are connected by intermolecular O—H
O hydrogen bonds, resulting in zigzag chains running along the [101] axis.
Supporting information
CCDC reference: 269849
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.051
- wR factor = 0.155
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT414_ALERT_2_B Short Intra D-H..H-X H3C .. H30B .. 1.87 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H2 .. H4C .. 2.05 Ang.
Alert level C
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.57 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C33
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C37
PLAT354_ALERT_3_C Short O-H Bond (0.82A) O2 - H2 ... 0.71 Ang.
PLAT390_ALERT_3_C Deviating Methyl C16 X-C-H Bond Angle ...... 117.60 Deg.
PLAT414_ALERT_2_C Short Intra D-H..H-X H2 .. H17B .. 1.94 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X H3C .. H31B .. 1.92 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C2 H4 O2
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
8 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
5 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
Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
C36H50O3·C2H4O2 | F(000) = 1288 |
Mr = 590.81 | Dx = 1.118 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 970 reflections |
a = 12.838 (7) Å | θ = 2.2–27.0° |
b = 16.250 (9) Å | µ = 0.07 mm−1 |
c = 17.221 (9) Å | T = 293 K |
β = 102.376 (11)° | Block, brown |
V = 3509 (3) Å3 | 0.50 × 0.46 × 0.41 mm |
Z = 4 | |
Data collection top
Bruker AXS SMART 1000 CCD diffractometer | 7661 independent reflections |
Radiation source: fine-focus sealed tube | 5405 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scan | θmax = 27.1°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→15 |
Tmin = 0.968, Tmax = 0.970 | k = −12→20 |
19669 measured reflections | l = −18→22 |
Refinement top
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0705P)2 + 1.1965P] where P = (Fo2 + 2Fc2)/3 |
7661 reflections | (Δ/σ)max < 0.001 |
416 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
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 | 0.66361 (11) | 0.59188 (8) | 1.03155 (7) | 0.0573 (4) | |
O3 | 0.34566 (10) | 0.86671 (8) | 0.64644 (8) | 0.0618 (4) | |
H3C | 0.2856 | 0.8505 | 0.6258 | 0.093* | |
C2 | 0.55390 (12) | 0.58348 (10) | 0.90324 (9) | 0.0373 (3) | |
C27 | 0.49396 (12) | 0.83697 (9) | 0.74696 (9) | 0.0384 (3) | |
C23 | 0.49458 (12) | 0.71654 (9) | 0.83116 (9) | 0.0390 (4) | |
C25 | 0.33688 (12) | 0.74613 (10) | 0.72845 (9) | 0.0371 (3) | |
C24 | 0.39136 (12) | 0.69863 (10) | 0.79114 (9) | 0.0385 (3) | |
H24A | 0.3573 | 0.6530 | 0.8069 | 0.046* | |
C6 | 0.65728 (12) | 0.45973 (10) | 0.97379 (9) | 0.0402 (4) | |
C28 | 0.54247 (12) | 0.78683 (10) | 0.80896 (10) | 0.0407 (4) | |
H28A | 0.6103 | 0.8008 | 0.8372 | 0.049* | |
C13 | 0.89845 (13) | 0.34523 (11) | 1.06487 (10) | 0.0438 (4) | |
H13A | 0.9399 | 0.3927 | 1.0705 | 0.053* | |
C7 | 0.74196 (13) | 0.43523 (10) | 1.02850 (10) | 0.0441 (4) | |
H7A | 0.7759 | 0.4760 | 1.0627 | 0.053* | |
O2 | 0.93087 (13) | 0.12460 (10) | 1.09032 (11) | 0.0685 (4) | |
C26 | 0.39015 (12) | 0.81495 (10) | 0.70677 (9) | 0.0394 (4) | |
C11 | 0.88329 (14) | 0.20006 (10) | 1.07209 (11) | 0.0455 (4) | |
C22 | 0.55428 (12) | 0.66540 (10) | 0.89551 (10) | 0.0410 (4) | |
H22A | 0.5986 | 0.6937 | 0.9367 | 0.049* | |
C9 | 0.72733 (14) | 0.28164 (11) | 1.03400 (10) | 0.0457 (4) | |
H9A | 0.6536 | 0.2864 | 1.0188 | 0.055* | |
C5 | 0.59556 (15) | 0.40525 (10) | 0.90952 (10) | 0.0474 (4) | |
H5A | 0.5333 | 0.3838 | 0.9262 | 0.057* | |
H5B | 0.6397 | 0.3589 | 0.9014 | 0.057* | |
C12 | 0.94881 (13) | 0.26974 (11) | 1.07981 (10) | 0.0429 (4) | |
C29 | 0.22266 (12) | 0.72271 (11) | 0.68598 (10) | 0.0428 (4) | |
C33 | 0.54929 (13) | 0.91424 (10) | 0.72413 (11) | 0.0453 (4) | |
C8 | 0.78839 (13) | 0.35278 (10) | 1.04179 (10) | 0.0434 (4) | |
C1 | 0.62757 (12) | 0.54817 (10) | 0.97421 (9) | 0.0390 (4) | |
C10 | 0.77153 (14) | 0.20380 (10) | 1.04795 (10) | 0.0443 (4) | |
C3 | 0.49290 (14) | 0.52485 (10) | 0.84288 (10) | 0.0437 (4) | |
H3A | 0.4701 | 0.5531 | 0.7925 | 0.052* | |
H3B | 0.4297 | 0.5063 | 0.8601 | 0.052* | |
C18 | 1.07118 (14) | 0.26534 (11) | 1.10634 (12) | 0.0499 (4) | |
C4 | 0.56030 (16) | 0.45139 (11) | 0.83185 (10) | 0.0495 (4) | |
H4A | 0.6225 | 0.4697 | 0.8131 | 0.059* | |
H4B | 0.5195 | 0.4149 | 0.7921 | 0.059* | |
C14 | 0.69990 (15) | 0.12668 (11) | 1.03749 (12) | 0.0518 (4) | |
C31 | 0.14418 (14) | 0.79115 (13) | 0.69589 (12) | 0.0575 (5) | |
H31A | 0.0734 | 0.7757 | 0.6691 | 0.086* | |
H31B | 0.1640 | 0.8413 | 0.6734 | 0.086* | |
H31C | 0.1460 | 0.7993 | 0.7514 | 0.086* | |
C30 | 0.21784 (15) | 0.70462 (13) | 0.59793 (11) | 0.0554 (5) | |
H30A | 0.2673 | 0.6615 | 0.5934 | 0.083* | |
H30B | 0.2362 | 0.7534 | 0.5724 | 0.083* | |
H30C | 0.1470 | 0.6876 | 0.5729 | 0.083* | |
C32 | 0.18483 (15) | 0.64483 (13) | 0.72132 (13) | 0.0625 (5) | |
H32A | 0.2317 | 0.6000 | 0.7163 | 0.094* | |
H32B | 0.1138 | 0.6317 | 0.6934 | 0.094* | |
H32C | 0.1852 | 0.6538 | 0.7765 | 0.094* | |
C36 | 0.66056 (16) | 0.92494 (13) | 0.77621 (15) | 0.0706 (6) | |
H36A | 0.7038 | 0.8783 | 0.7696 | 0.106* | |
H36B | 0.6555 | 0.9291 | 0.8309 | 0.106* | |
H36C | 0.6924 | 0.9741 | 0.7609 | 0.106* | |
C35 | 0.48565 (17) | 0.99056 (11) | 0.73778 (14) | 0.0630 (5) | |
H35A | 0.4147 | 0.9869 | 0.7058 | 0.094* | |
H35B | 0.5200 | 1.0389 | 0.7232 | 0.094* | |
H35C | 0.4824 | 0.9938 | 0.7929 | 0.094* | |
C21 | 1.12312 (16) | 0.34898 (14) | 1.10141 (16) | 0.0720 (6) | |
H21A | 1.0966 | 0.3875 | 1.1348 | 0.108* | |
H21B | 1.1064 | 0.3681 | 1.0474 | 0.108* | |
H21C | 1.1990 | 0.3440 | 1.1190 | 0.108* | |
C20 | 1.10169 (17) | 0.23702 (16) | 1.19255 (14) | 0.0708 (6) | |
H20A | 1.0720 | 0.2741 | 1.2254 | 0.106* | |
H20B | 1.1780 | 0.2365 | 1.2096 | 0.106* | |
H20C | 1.0744 | 0.1826 | 1.1970 | 0.106* | |
C17 | 0.7070 (2) | 0.08312 (16) | 1.11723 (16) | 0.0690 (6) | |
C34 | 0.5611 (2) | 0.90926 (15) | 0.63765 (14) | 0.0734 (6) | |
H34A | 0.6011 | 0.8609 | 0.6306 | 0.110* | |
H34B | 0.5978 | 0.9572 | 0.6250 | 0.110* | |
H34C | 0.4917 | 0.9065 | 0.6031 | 0.110* | |
C15 | 0.58270 (17) | 0.14913 (15) | 1.00676 (17) | 0.0768 (7) | |
H15A | 0.5745 | 0.1767 | 0.9565 | 0.115* | |
H15B | 0.5597 | 0.1849 | 1.0442 | 0.115* | |
H15C | 0.5403 | 0.0999 | 1.0003 | 0.115* | |
C19 | 1.11848 (18) | 0.20820 (16) | 1.05198 (16) | 0.0755 (7) | |
H19A | 1.1946 | 0.2066 | 1.0696 | 0.113* | |
H19B | 1.1004 | 0.2284 | 0.9984 | 0.113* | |
H19C | 1.0900 | 0.1538 | 1.0539 | 0.113* | |
C16 | 0.7293 (3) | 0.06751 (18) | 0.97664 (18) | 0.0745 (7) | |
O4 | 1.09089 (16) | 0.00155 (12) | 1.13485 (17) | 0.1178 (8) | |
H4C | 1.0562 | 0.0439 | 1.1235 | 0.177* | |
C37 | 1.0287 (2) | −0.05870 (14) | 1.12943 (14) | 0.0707 (6) | |
O5 | 0.93284 (18) | −0.04827 (13) | 1.11158 (19) | 0.1410 (11) | |
C38 | 1.0757 (3) | −0.13989 (16) | 1.15135 (19) | 0.0934 (9) | |
H38C | 1.0201 | −0.1804 | 1.1450 | 0.140* | |
H38B | 1.1139 | −0.1390 | 1.2058 | 0.140* | |
H38A | 1.1238 | −0.1534 | 1.1176 | 0.140* | |
H17A | 0.6801 (19) | 0.1194 (15) | 1.1551 (15) | 0.079 (7)* | |
H17C | 0.662 (2) | 0.0355 (16) | 1.1069 (14) | 0.085 (7)* | |
H16C | 0.678 (2) | 0.0198 (18) | 0.9703 (16) | 0.096 (8)* | |
H16A | 0.718 (2) | 0.0955 (17) | 0.9262 (18) | 0.097 (9)* | |
H17B | 0.782 (2) | 0.0628 (15) | 1.1425 (14) | 0.082 (8)* | |
H16B | 0.802 (3) | 0.0487 (17) | 0.9856 (16) | 0.098 (9)* | |
H2 | 0.903 (4) | 0.088 (3) | 1.096 (3) | 0.164 (18)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0654 (8) | 0.0435 (7) | 0.0490 (7) | 0.0103 (6) | −0.0188 (6) | −0.0062 (6) |
O3 | 0.0466 (7) | 0.0606 (8) | 0.0668 (8) | −0.0091 (6) | −0.0130 (6) | 0.0297 (7) |
C2 | 0.0340 (8) | 0.0388 (8) | 0.0361 (8) | 0.0041 (6) | 0.0009 (6) | 0.0010 (6) |
C27 | 0.0341 (8) | 0.0339 (8) | 0.0454 (9) | 0.0028 (6) | 0.0046 (6) | −0.0001 (7) |
C23 | 0.0382 (8) | 0.0356 (8) | 0.0393 (8) | 0.0056 (6) | −0.0001 (6) | −0.0002 (6) |
C25 | 0.0311 (7) | 0.0387 (8) | 0.0392 (8) | 0.0031 (6) | 0.0026 (6) | 0.0014 (7) |
C24 | 0.0361 (8) | 0.0356 (8) | 0.0415 (8) | 0.0017 (6) | 0.0031 (6) | 0.0028 (6) |
C6 | 0.0378 (8) | 0.0384 (8) | 0.0420 (8) | 0.0042 (6) | 0.0033 (6) | 0.0021 (7) |
C28 | 0.0327 (8) | 0.0363 (8) | 0.0482 (9) | 0.0024 (6) | −0.0022 (7) | −0.0030 (7) |
C13 | 0.0407 (9) | 0.0416 (9) | 0.0469 (9) | 0.0051 (7) | 0.0044 (7) | 0.0070 (7) |
C7 | 0.0403 (9) | 0.0406 (9) | 0.0474 (9) | 0.0051 (7) | 0.0003 (7) | 0.0022 (7) |
O2 | 0.0602 (9) | 0.0410 (8) | 0.1052 (13) | 0.0161 (7) | 0.0196 (8) | 0.0130 (8) |
C26 | 0.0349 (8) | 0.0390 (8) | 0.0410 (8) | 0.0038 (6) | 0.0008 (6) | 0.0056 (7) |
C11 | 0.0471 (9) | 0.0390 (9) | 0.0514 (10) | 0.0110 (7) | 0.0127 (8) | 0.0060 (7) |
C22 | 0.0369 (8) | 0.0401 (9) | 0.0407 (8) | 0.0021 (6) | −0.0034 (6) | −0.0010 (7) |
C9 | 0.0380 (8) | 0.0477 (10) | 0.0493 (10) | 0.0060 (7) | 0.0048 (7) | 0.0040 (8) |
C5 | 0.0517 (10) | 0.0371 (9) | 0.0484 (10) | 0.0057 (7) | −0.0002 (8) | −0.0018 (7) |
C12 | 0.0384 (8) | 0.0448 (9) | 0.0463 (9) | 0.0083 (7) | 0.0104 (7) | 0.0057 (7) |
C29 | 0.0316 (8) | 0.0479 (9) | 0.0452 (9) | −0.0015 (7) | 0.0005 (7) | 0.0059 (7) |
C33 | 0.0387 (8) | 0.0371 (9) | 0.0586 (10) | −0.0009 (7) | 0.0070 (7) | 0.0035 (8) |
C8 | 0.0408 (9) | 0.0434 (9) | 0.0432 (9) | 0.0081 (7) | 0.0027 (7) | 0.0047 (7) |
C1 | 0.0357 (8) | 0.0378 (8) | 0.0396 (8) | 0.0025 (6) | −0.0005 (6) | 0.0000 (7) |
C10 | 0.0450 (9) | 0.0419 (9) | 0.0468 (9) | 0.0024 (7) | 0.0117 (7) | 0.0022 (7) |
C3 | 0.0453 (9) | 0.0408 (9) | 0.0385 (8) | 0.0012 (7) | −0.0053 (7) | 0.0009 (7) |
C18 | 0.0379 (9) | 0.0485 (10) | 0.0635 (11) | 0.0104 (7) | 0.0114 (8) | 0.0069 (8) |
C4 | 0.0584 (11) | 0.0443 (10) | 0.0417 (9) | 0.0025 (8) | 0.0018 (8) | −0.0061 (7) |
C14 | 0.0501 (10) | 0.0447 (10) | 0.0613 (11) | −0.0022 (8) | 0.0139 (8) | −0.0040 (8) |
C31 | 0.0358 (9) | 0.0707 (13) | 0.0634 (12) | 0.0084 (8) | 0.0048 (8) | 0.0052 (10) |
C30 | 0.0480 (10) | 0.0633 (12) | 0.0496 (10) | −0.0058 (9) | −0.0014 (8) | −0.0027 (9) |
C32 | 0.0439 (10) | 0.0663 (13) | 0.0701 (13) | −0.0166 (9) | −0.0041 (9) | 0.0163 (10) |
C36 | 0.0486 (11) | 0.0508 (12) | 0.1040 (18) | −0.0119 (9) | −0.0026 (11) | 0.0123 (11) |
C35 | 0.0615 (12) | 0.0380 (10) | 0.0908 (15) | 0.0045 (9) | 0.0196 (11) | 0.0062 (10) |
C21 | 0.0413 (10) | 0.0633 (13) | 0.1088 (18) | 0.0021 (9) | 0.0103 (11) | 0.0117 (13) |
C20 | 0.0517 (12) | 0.0863 (16) | 0.0699 (14) | 0.0134 (11) | 0.0029 (10) | 0.0153 (12) |
C17 | 0.0791 (17) | 0.0557 (13) | 0.0775 (16) | −0.0122 (12) | 0.0283 (13) | 0.0036 (12) |
C34 | 0.0845 (16) | 0.0676 (14) | 0.0760 (15) | −0.0177 (12) | 0.0350 (12) | 0.0007 (11) |
C15 | 0.0526 (12) | 0.0611 (13) | 0.1120 (19) | −0.0078 (10) | 0.0073 (12) | −0.0091 (13) |
C19 | 0.0534 (12) | 0.0845 (16) | 0.0954 (17) | 0.0095 (11) | 0.0314 (12) | −0.0109 (13) |
C16 | 0.0814 (18) | 0.0672 (15) | 0.0786 (17) | −0.0078 (14) | 0.0253 (14) | −0.0216 (13) |
O4 | 0.0754 (12) | 0.0757 (13) | 0.198 (2) | 0.0037 (10) | 0.0208 (13) | 0.0070 (14) |
C37 | 0.0830 (17) | 0.0585 (13) | 0.0737 (14) | 0.0044 (12) | 0.0236 (12) | 0.0045 (11) |
O5 | 0.0750 (14) | 0.0793 (14) | 0.251 (3) | −0.0062 (11) | −0.0049 (16) | 0.0283 (16) |
C38 | 0.107 (2) | 0.0741 (17) | 0.108 (2) | 0.0187 (15) | 0.0435 (17) | 0.0280 (15) |
Geometric parameters (Å, º) top
O1—C1 | 1.2239 (19) | C18—C19 | 1.533 (3) |
O2—C11 | 1.376 (2) | C4—H4A | 0.9700 |
O3—C26 | 1.3634 (19) | C4—H4B | 0.9700 |
O3—H3C | 0.8200 | C14—C16 | 1.528 (3) |
C1—C2 | 1.491 (2) | C14—C15 | 1.528 (3) |
C2—C3 | 1.501 (2) | C14—C17 | 1.530 (3) |
C2—C22 | 1.338 (2) | C31—H31A | 0.9600 |
C3—C4 | 1.510 (2) | C31—H31B | 0.9600 |
C4—C5 | 1.515 (2) | C31—H31C | 0.9600 |
C5—C6 | 1.504 (2) | C30—H30A | 0.9600 |
C6—C7 | 1.337 (2) | C30—H30B | 0.9600 |
C7—C8 | 1.464 (2) | C30—H30C | 0.9600 |
C22—C23 | 1.464 (2) | C32—H32A | 0.9600 |
C27—C28 | 1.381 (2) | C32—H32B | 0.9600 |
C27—C26 | 1.410 (2) | C32—H32C | 0.9600 |
C27—C33 | 1.535 (2) | C36—H36A | 0.9600 |
C23—C24 | 1.387 (2) | C36—H36B | 0.9600 |
C23—C28 | 1.389 (2) | C36—H36C | 0.9600 |
C25—C24 | 1.388 (2) | C35—H35A | 0.9600 |
C25—C26 | 1.402 (2) | C35—H35B | 0.9600 |
C25—C29 | 1.540 (2) | C35—H35C | 0.9600 |
C24—H24A | 0.9300 | C21—H21A | 0.9600 |
C6—C1 | 1.487 (2) | C21—H21B | 0.9600 |
C28—H28A | 0.9300 | C21—H21C | 0.9600 |
C13—C12 | 1.385 (2) | C20—H20A | 0.9600 |
C13—C8 | 1.389 (2) | C20—H20B | 0.9600 |
C13—H13A | 0.9300 | C20—H20C | 0.9600 |
C7—H7A | 0.9300 | C17—H17A | 0.99 (3) |
O2—C11 | 1.376 (2) | C17—H17C | 0.96 (3) |
O2—H2 | 0.71 (4) | C17—H17B | 1.02 (3) |
C11—C12 | 1.400 (3) | C34—H34A | 0.9600 |
C11—C10 | 1.407 (3) | C34—H34B | 0.9600 |
C22—H22A | 0.9300 | C34—H34C | 0.9600 |
C9—C10 | 1.386 (2) | C15—H15A | 0.9600 |
C9—C8 | 1.387 (3) | C15—H15B | 0.9600 |
C9—H9A | 0.9300 | C15—H15C | 0.9600 |
C5—H5A | 0.9700 | C19—H19A | 0.9600 |
C5—H5B | 0.9700 | C19—H19B | 0.9600 |
C12—C18 | 1.541 (2) | C19—H19C | 0.9600 |
C29—C32 | 1.528 (3) | C16—H16C | 1.01 (3) |
C29—C30 | 1.533 (3) | C16—H16A | 0.96 (3) |
C29—C31 | 1.535 (3) | C16—H16B | 0.96 (3) |
C33—C36 | 1.525 (3) | O4—C37 | 1.254 (3) |
C33—C35 | 1.531 (3) | O4—H4C | 0.8200 |
C33—C34 | 1.531 (3) | C37—O5 | 1.215 (3) |
C10—C14 | 1.542 (3) | C37—C38 | 1.466 (3) |
C3—H3A | 0.9700 | C38—H38C | 0.9600 |
C3—H3B | 0.9700 | C38—H38B | 0.9600 |
C18—C20 | 1.523 (3) | C38—H38A | 0.9600 |
C18—C21 | 1.524 (3) | | |
| | | |
C26—O3—H3C | 109.5 | C16—C14—C15 | 106.4 (2) |
C22—C2—C1 | 116.71 (14) | C16—C14—C17 | 110.4 (2) |
C22—C2—C3 | 125.11 (14) | C15—C14—C17 | 106.64 (19) |
C1—C2—C3 | 117.95 (14) | C16—C14—C10 | 111.26 (18) |
C28—C27—C26 | 116.87 (15) | C15—C14—C10 | 111.39 (16) |
C28—C27—C33 | 121.61 (14) | C17—C14—C10 | 110.59 (17) |
C26—C27—C33 | 121.50 (14) | C29—C31—H31A | 109.5 |
C24—C23—C28 | 117.89 (14) | C29—C31—H31B | 109.5 |
C24—C23—C22 | 123.13 (15) | H31A—C31—H31B | 109.5 |
C28—C23—C22 | 118.98 (14) | C29—C31—H31C | 109.5 |
C24—C25—C26 | 117.22 (14) | H31A—C31—H31C | 109.5 |
C24—C25—C29 | 120.11 (14) | H31B—C31—H31C | 109.5 |
C26—C25—C29 | 122.67 (14) | C29—C30—H30A | 109.5 |
C23—C24—C25 | 122.55 (15) | C29—C30—H30B | 109.5 |
C23—C24—H24A | 118.7 | H30A—C30—H30B | 109.5 |
C25—C24—H24A | 118.7 | C29—C30—H30C | 109.5 |
C7—C6—C1 | 117.05 (15) | H30A—C30—H30C | 109.5 |
C7—C6—C5 | 124.32 (15) | H30B—C30—H30C | 109.5 |
C1—C6—C5 | 118.51 (13) | C29—C32—H32A | 109.5 |
C27—C28—C23 | 123.04 (15) | C29—C32—H32B | 109.5 |
C27—C28—H28A | 118.5 | H32A—C32—H32B | 109.5 |
C23—C28—H28A | 118.5 | C29—C32—H32C | 109.5 |
C12—C13—C8 | 122.50 (16) | H32A—C32—H32C | 109.5 |
C12—C13—H13A | 118.8 | H32B—C32—H32C | 109.5 |
C8—C13—H13A | 118.8 | C33—C36—H36A | 109.5 |
C6—C7—C8 | 128.66 (16) | C33—C36—H36B | 109.5 |
C6—C7—H7A | 115.7 | H36A—C36—H36B | 109.5 |
C8—C7—H7A | 115.7 | C33—C36—H36C | 109.5 |
C11—O2—H2 | 125 (4) | H36A—C36—H36C | 109.5 |
O3—C26—C25 | 123.11 (14) | H36B—C36—H36C | 109.5 |
O3—C26—C27 | 114.52 (14) | C33—C35—H35A | 109.5 |
C25—C26—C27 | 122.36 (14) | C33—C35—H35B | 109.5 |
O2—C11—C12 | 118.09 (16) | H35A—C35—H35B | 109.5 |
O2—C11—C10 | 118.73 (16) | C33—C35—H35C | 109.5 |
C12—C11—C10 | 123.16 (15) | H35A—C35—H35C | 109.5 |
C2—C22—C23 | 128.89 (15) | H35B—C35—H35C | 109.5 |
C2—C22—H22A | 115.6 | C18—C21—H21A | 109.5 |
C23—C22—H22A | 115.6 | C18—C21—H21B | 109.5 |
C10—C9—C8 | 122.81 (16) | H21A—C21—H21B | 109.5 |
C10—C9—H9A | 118.6 | C18—C21—H21C | 109.5 |
C8—C9—H9A | 118.6 | H21A—C21—H21C | 109.5 |
C6—C5—C4 | 111.65 (15) | H21B—C21—H21C | 109.5 |
C6—C5—H5A | 109.3 | C18—C20—H20A | 109.5 |
C4—C5—H5A | 109.3 | C18—C20—H20B | 109.5 |
C6—C5—H5B | 109.3 | H20A—C20—H20B | 109.5 |
C4—C5—H5B | 109.3 | C18—C20—H20C | 109.5 |
H5A—C5—H5B | 108.0 | H20A—C20—H20C | 109.5 |
C13—C12—C11 | 116.86 (15) | H20B—C20—H20C | 109.5 |
C13—C12—C18 | 120.13 (16) | C14—C17—H17A | 110.6 (14) |
C11—C12—C18 | 122.98 (15) | C14—C17—H17C | 106.8 (15) |
C32—C29—C30 | 106.64 (16) | H17A—C17—H17C | 109 (2) |
C32—C29—C31 | 106.48 (16) | C14—C17—H17B | 113.7 (14) |
C30—C29—C31 | 111.14 (15) | H17A—C17—H17B | 110 (2) |
C32—C29—C25 | 111.55 (14) | H17C—C17—H17B | 107 (2) |
C30—C29—C25 | 110.47 (14) | C33—C34—H34A | 109.5 |
C31—C29—C25 | 110.44 (15) | C33—C34—H34B | 109.5 |
C36—C33—C35 | 106.31 (17) | H34A—C34—H34B | 109.5 |
C36—C33—C34 | 107.62 (18) | C33—C34—H34C | 109.5 |
C35—C33—C34 | 111.07 (17) | H34A—C34—H34C | 109.5 |
C36—C33—C27 | 111.67 (15) | H34B—C34—H34C | 109.5 |
C35—C33—C27 | 109.39 (15) | C14—C15—H15A | 109.5 |
C34—C33—C27 | 110.70 (15) | C14—C15—H15B | 109.5 |
C9—C8—C13 | 118.25 (15) | H15A—C15—H15B | 109.5 |
C9—C8—C7 | 123.00 (15) | C14—C15—H15C | 109.5 |
C13—C8—C7 | 118.73 (16) | H15A—C15—H15C | 109.5 |
O1—C1—C6 | 120.77 (14) | H15B—C15—H15C | 109.5 |
O1—C1—C2 | 120.13 (15) | C18—C19—H19A | 109.5 |
C6—C1—C2 | 119.10 (13) | C18—C19—H19B | 109.5 |
C9—C10—C11 | 116.39 (16) | H19A—C19—H19B | 109.5 |
C9—C10—C14 | 120.64 (16) | C18—C19—H19C | 109.5 |
C11—C10—C14 | 122.97 (15) | H19A—C19—H19C | 109.5 |
C2—C3—C4 | 111.16 (14) | H19B—C19—H19C | 109.5 |
C2—C3—H3A | 109.4 | C14—C16—H16C | 108.0 (15) |
C4—C3—H3A | 109.4 | C14—C16—H16A | 108.0 (17) |
C2—C3—H3B | 109.4 | H16C—C16—H16A | 107 (2) |
C4—C3—H3B | 109.4 | C14—C16—H16B | 117.7 (17) |
H3A—C3—H3B | 108.0 | H16C—C16—H16B | 111 (2) |
C20—C18—C21 | 107.43 (18) | H16A—C16—H16B | 104 (2) |
C20—C18—C19 | 111.06 (18) | C37—O4—H4C | 109.5 |
C21—C18—C19 | 105.71 (18) | O5—C37—O4 | 120.3 (2) |
C20—C18—C12 | 109.63 (15) | O5—C37—C38 | 121.9 (3) |
C21—C18—C12 | 111.87 (15) | O4—C37—C38 | 117.6 (3) |
C19—C18—C12 | 111.05 (17) | C37—C38—H38C | 109.5 |
C3—C4—C5 | 110.55 (15) | C37—C38—H38B | 109.5 |
C3—C4—H4A | 109.5 | H38C—C38—H38B | 109.5 |
C5—C4—H4A | 109.5 | C37—C38—H38A | 109.5 |
C3—C4—H4B | 109.5 | H38C—C38—H38A | 109.5 |
C5—C4—H4B | 109.5 | H38B—C38—H38A | 109.5 |
H4A—C4—H4B | 108.1 | | |
| | | |
C28—C23—C24—C25 | 2.7 (2) | C26—C27—C33—C35 | 62.4 (2) |
C22—C23—C24—C25 | −177.81 (15) | C28—C27—C33—C34 | 121.27 (19) |
C26—C25—C24—C23 | −0.7 (2) | C26—C27—C33—C34 | −60.3 (2) |
C29—C25—C24—C23 | 179.55 (15) | C10—C9—C8—C13 | −0.3 (3) |
C26—C27—C28—C23 | 1.4 (2) | C10—C9—C8—C7 | −178.87 (16) |
C33—C27—C28—C23 | 179.95 (15) | C12—C13—C8—C9 | 0.3 (3) |
C24—C23—C28—C27 | −3.1 (2) | C12—C13—C8—C7 | 179.03 (16) |
C22—C23—C28—C27 | 177.39 (15) | C6—C7—C8—C9 | −37.8 (3) |
C1—C6—C7—C8 | 179.83 (17) | C6—C7—C8—C13 | 143.60 (19) |
C5—C6—C7—C8 | −4.3 (3) | C7—C6—C1—O1 | −15.3 (3) |
C24—C25—C26—O3 | −179.87 (16) | C5—C6—C1—O1 | 168.52 (17) |
C29—C25—C26—O3 | −0.1 (3) | C7—C6—C1—C2 | 163.99 (16) |
C24—C25—C26—C27 | −1.1 (2) | C5—C6—C1—C2 | −12.1 (2) |
C29—C25—C26—C27 | 178.70 (15) | C22—C2—C1—O1 | 18.8 (2) |
C28—C27—C26—O3 | 179.61 (15) | C3—C2—C1—O1 | −166.49 (16) |
C33—C27—C26—O3 | 1.1 (2) | C22—C2—C1—C6 | −160.53 (16) |
C28—C27—C26—C25 | 0.7 (2) | C3—C2—C1—C6 | 14.2 (2) |
C33—C27—C26—C25 | −177.82 (15) | C8—C9—C10—C11 | 1.0 (3) |
C1—C2—C22—C23 | 177.24 (16) | C8—C9—C10—C14 | −179.32 (16) |
C3—C2—C22—C23 | 2.9 (3) | O2—C11—C10—C9 | 177.00 (16) |
C24—C23—C22—C2 | 36.2 (3) | C12—C11—C10—C9 | −1.9 (3) |
C28—C23—C22—C2 | −144.26 (18) | O2—C11—C10—C14 | −2.7 (3) |
C7—C6—C5—C4 | −141.99 (18) | C12—C11—C10—C14 | 178.41 (16) |
C1—C6—C5—C4 | 33.8 (2) | C22—C2—C3—C4 | 136.35 (17) |
C8—C13—C12—C11 | −1.2 (3) | C1—C2—C3—C4 | −37.9 (2) |
C8—C13—C12—C18 | −179.18 (16) | C13—C12—C18—C20 | 111.0 (2) |
O2—C11—C12—C13 | −176.91 (17) | C11—C12—C18—C20 | −66.8 (2) |
C10—C11—C12—C13 | 2.0 (3) | C13—C12—C18—C21 | −8.0 (3) |
O2—C11—C12—C18 | 1.0 (3) | C11—C12—C18—C21 | 174.11 (18) |
C10—C11—C12—C18 | 179.95 (16) | C13—C12—C18—C19 | −125.9 (2) |
C24—C25—C29—C32 | −0.7 (2) | C11—C12—C18—C19 | 56.3 (2) |
C26—C25—C29—C32 | 179.57 (17) | C2—C3—C4—C5 | 60.0 (2) |
C24—C25—C29—C30 | −119.10 (17) | C6—C5—C4—C3 | −58.0 (2) |
C26—C25—C29—C30 | 61.1 (2) | C9—C10—C14—C16 | 121.8 (2) |
C24—C25—C29—C31 | 117.53 (18) | C11—C10—C14—C16 | −58.5 (3) |
C26—C25—C29—C31 | −62.2 (2) | C9—C10—C14—C15 | 3.3 (3) |
C28—C27—C33—C36 | 1.4 (2) | C11—C10—C14—C15 | −177.07 (18) |
C26—C27—C33—C36 | 179.85 (17) | C9—C10—C14—C17 | −115.1 (2) |
C28—C27—C33—C35 | −116.02 (19) | C11—C10—C14—C17 | 64.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3C···O1i | 0.82 | 2.21 | 2.801 (2) | 129 |
O2—H2···O5 | 0.71 (4) | 2.25 (4) | 2.832 (3) | 140 (5) |
O4—H4C···O2 | 0.82 | 2.06 | 2.851 (3) | 162 |
Symmetry code: (i) x−1/2, −y+3/2, z−1/2. |