The title compound, (23
R,24
S)-16b,23:16a,24-diepoxy-15a,25-dihydroxy-9,19-cyclolanostane-3-
O-β-
D-xylopyranoside methanol solvate, C
35H
56O
9·CH
4O, is a cycloartane triterpene glycoside which was isolated from the rhizomes of
Actaea asiatica. The molecule contains five six-membered rings, two five-membered rings and a three-membered ring. The crystal structure is stabilized by intra- and intermolecular O—H
O hydrogen bonds.
Supporting information
CCDC reference: 627970
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.057
- wR factor = 0.183
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT413_ALERT_2_C Short Inter XH3 .. XHn H2A .. H29A .. 2.14 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 28.32
From the CIF: _reflns_number_total 4482
Count of symmetry unique reflns 4664
Completeness (_total/calc) 96.10%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C31 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C33 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34 = . S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
15 ALERT level G = General alerts; check
15 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
1 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, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.
(23
R, 24S)-16
b,23:16
a,24-diepoxy-15
a,25-dihydroxy-9,
19-cyclolanostane-3-
O-b-
D-xylopyranoside
top
Crystal data top
C35H56O9·CH4O | F(000) = 712 |
Mr = 652.84 | Dx = 1.252 Mg m−3 |
Monoclinic, P21 | Melting point: 268 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 14.500 (3) Å | Cell parameters from 3138 reflections |
b = 6.9301 (14) Å | θ = 2.7–26.4° |
c = 17.267 (4) Å | µ = 0.09 mm−1 |
β = 93.352 (4)° | T = 294 K |
V = 1732.1 (6) Å3 | Block, colourless |
Z = 2 | 0.22 × 0.18 × 0.10 mm |
Data collection top
Bruker SMART 1000 diffractometer | 4482 independent reflections |
Radiation source: fine-focus sealed tube | 2630 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 28.3°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −18→19 |
Tmin = 0.981, Tmax = 0.991 | k = −9→8 |
10507 measured reflections | l = −12→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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.183 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0865P)2 + 0.4276P] where P = (Fo2 + 2Fc2)/3 |
4482 reflections | (Δ/σ)max = 0.001 |
449 parameters | Δρmax = 0.37 e Å−3 |
27 restraints | Δρmin = −0.28 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 | Occ. (<1) |
O1 | 0.0685 (2) | 0.6504 (5) | 0.77002 (19) | 0.0404 (8) | |
O2 | 0.2307 (3) | 1.2168 (6) | 0.2991 (2) | 0.0530 (10) | |
H2 | 0.2125 | 1.1787 | 0.2559 | 0.080* | |
O3 | 0.4451 (2) | 1.2107 (5) | 0.2602 (2) | 0.0435 (9) | |
O4 | 0.3335 (2) | 1.0563 (5) | 0.18862 (18) | 0.0393 (8) | |
O5 | 0.2841 (3) | 1.2263 (6) | 0.0432 (2) | 0.0558 (11) | |
H5 | 0.2644 | 1.3112 | 0.0136 | 0.084* | |
O6 | −0.1036 (3) | 0.7206 (6) | 0.8355 (2) | 0.0510 (9) | |
H6 | −0.1040 | 0.8097 | 0.8667 | 0.076* | |
O7 | −0.1433 (3) | 0.4648 (7) | 0.9613 (2) | 0.0625 (12) | |
H7 | −0.1943 | 0.5077 | 0.9473 | 0.094* | |
O8 | −0.0860 (3) | 0.0677 (6) | 0.9306 (2) | 0.0582 (11) | |
H8 | −0.1194 | 0.0849 | 0.9667 | 0.087* | |
O9 | 0.0770 (2) | 0.3564 (6) | 0.8289 (2) | 0.0494 (10) | |
C1 | 0.2000 (4) | 0.5072 (8) | 0.5946 (3) | 0.0518 (14) | |
H1A | 0.2568 | 0.4350 | 0.5903 | 0.062* | |
H1B | 0.1510 | 0.4409 | 0.5645 | 0.062* | |
C2 | 0.1760 (5) | 0.5181 (8) | 0.6801 (3) | 0.0568 (16) | |
H2A | 0.1672 | 0.3887 | 0.6998 | 0.068* | |
H2B | 0.2270 | 0.5767 | 0.7106 | 0.068* | |
C3 | 0.0888 (4) | 0.6356 (7) | 0.6891 (3) | 0.0402 (12) | |
H3 | 0.0372 | 0.5691 | 0.6612 | 0.048* | |
C4 | 0.0950 (3) | 0.8417 (7) | 0.6561 (3) | 0.0362 (11) | |
C5 | 0.1231 (3) | 0.8227 (7) | 0.5704 (3) | 0.0360 (11) | |
H5A | 0.0746 | 0.7436 | 0.5445 | 0.043* | |
C6 | 0.1207 (4) | 1.0126 (8) | 0.5261 (3) | 0.0503 (14) | |
H6A | 0.1626 | 1.1040 | 0.5522 | 0.060* | |
H6B | 0.0589 | 1.0663 | 0.5250 | 0.060* | |
C7 | 0.1492 (3) | 0.9800 (9) | 0.4428 (3) | 0.0498 (14) | |
H7A | 0.1123 | 0.8772 | 0.4187 | 0.060* | |
H7B | 0.1384 | 1.0966 | 0.4125 | 0.060* | |
C8 | 0.2510 (3) | 0.9263 (7) | 0.4443 (3) | 0.0349 (11) | |
H8A | 0.2841 | 1.0338 | 0.4702 | 0.042* | |
C9 | 0.2731 (3) | 0.7465 (7) | 0.4956 (3) | 0.0339 (10) | |
C10 | 0.2114 (3) | 0.7093 (7) | 0.5631 (3) | 0.0346 (11) | |
C11 | 0.3121 (3) | 0.5708 (8) | 0.4537 (3) | 0.0409 (12) | |
H11A | 0.2607 | 0.5017 | 0.4281 | 0.049* | |
H11B | 0.3404 | 0.4852 | 0.4927 | 0.049* | |
C12 | 0.3836 (4) | 0.6122 (8) | 0.3930 (3) | 0.0431 (12) | |
H12A | 0.4439 | 0.5692 | 0.4134 | 0.052* | |
H12B | 0.3675 | 0.5376 | 0.3466 | 0.052* | |
C13 | 0.3897 (3) | 0.8272 (7) | 0.3707 (3) | 0.0342 (11) | |
C14 | 0.2901 (3) | 0.9103 (7) | 0.3637 (3) | 0.0315 (10) | |
C15 | 0.3080 (3) | 1.1068 (7) | 0.3262 (3) | 0.0373 (11) | |
H15 | 0.3409 | 1.1850 | 0.3662 | 0.045* | |
C16 | 0.3780 (3) | 1.0627 (7) | 0.2652 (3) | 0.0338 (11) | |
C17 | 0.4242 (3) | 0.8698 (8) | 0.2888 (3) | 0.0362 (11) | |
H17 | 0.3990 | 0.7700 | 0.2533 | 0.043* | |
C18 | 0.4522 (3) | 0.9282 (9) | 0.4338 (3) | 0.0460 (13) | |
H18A | 0.4251 | 0.9172 | 0.4830 | 0.069* | |
H18B | 0.4585 | 1.0620 | 0.4208 | 0.069* | |
H18C | 0.5120 | 0.8682 | 0.4368 | 0.069* | |
C19 | 0.3063 (3) | 0.7942 (8) | 0.5770 (3) | 0.0390 (11) | |
H19A | 0.3106 | 0.9294 | 0.5913 | 0.047* | |
H19B | 0.3539 | 0.7127 | 0.6016 | 0.047* | |
C20 | 0.5298 (3) | 0.8809 (9) | 0.2797 (3) | 0.0461 (13) | |
H20 | 0.5565 | 0.9625 | 0.3217 | 0.055* | |
C21 | 0.5783 (4) | 0.6852 (10) | 0.2857 (4) | 0.0650 (18) | |
H21A | 0.5457 | 0.5943 | 0.2523 | 0.097* | |
H21B | 0.5792 | 0.6401 | 0.3383 | 0.097* | |
H21C | 0.6406 | 0.6984 | 0.2702 | 0.097* | |
C22 | 0.5470 (4) | 0.9815 (10) | 0.2023 (3) | 0.0564 (16) | |
H22A | 0.6115 | 1.0190 | 0.2021 | 0.068* | |
H22B | 0.5344 | 0.8915 | 0.1600 | 0.068* | |
C23 | 0.4865 (3) | 1.1594 (9) | 0.1895 (3) | 0.0452 (13) | |
H23 | 0.5223 | 1.2674 | 0.1703 | 0.054* | |
C24 | 0.4000 (3) | 1.1200 (8) | 0.1351 (3) | 0.0384 (11) | |
H24 | 0.4131 | 1.0142 | 0.0998 | 0.046* | |
C25 | 0.3637 (3) | 1.2957 (8) | 0.0876 (3) | 0.0411 (12) | |
C26 | 0.4351 (4) | 1.3507 (11) | 0.0298 (4) | 0.0684 (18) | |
H26A | 0.4551 | 1.2368 | 0.0039 | 0.103* | |
H26B | 0.4873 | 1.4106 | 0.0570 | 0.103* | |
H26C | 0.4080 | 1.4392 | −0.0077 | 0.103* | |
C27 | 0.3366 (4) | 1.4641 (9) | 0.1355 (4) | 0.0622 (16) | |
H27A | 0.3161 | 1.5679 | 0.1020 | 0.093* | |
H27B | 0.3889 | 1.5057 | 0.1680 | 0.093* | |
H27C | 0.2875 | 1.4268 | 0.1673 | 0.093* | |
C28 | 0.2263 (3) | 0.7921 (8) | 0.3082 (3) | 0.0424 (13) | |
H28A | 0.2151 | 0.6684 | 0.3309 | 0.064* | |
H28B | 0.2551 | 0.7745 | 0.2600 | 0.064* | |
H28C | 0.1688 | 0.8591 | 0.2989 | 0.064* | |
C29 | 0.1653 (4) | 0.9595 (8) | 0.7060 (3) | 0.0482 (13) | |
H29A | 0.1733 | 1.0835 | 0.6827 | 0.072* | |
H29B | 0.2234 | 0.8926 | 0.7098 | 0.072* | |
H29C | 0.1432 | 0.9760 | 0.7570 | 0.072* | |
C30 | −0.0014 (4) | 0.9357 (9) | 0.6572 (3) | 0.0542 (15) | |
H30A | −0.0252 | 0.9186 | 0.7075 | 0.081* | |
H30B | −0.0424 | 0.8758 | 0.6187 | 0.081* | |
H30C | 0.0033 | 1.0709 | 0.6462 | 0.081* | |
C31 | 0.0157 (3) | 0.5048 (7) | 0.7985 (3) | 0.0375 (11) | |
H31 | −0.0253 | 0.4519 | 0.7567 | 0.045* | |
C32 | −0.0412 (3) | 0.5761 (7) | 0.8640 (3) | 0.0366 (11) | |
H32 | −0.0001 | 0.6297 | 0.9056 | 0.044* | |
C33 | −0.0960 (3) | 0.4079 (8) | 0.8955 (3) | 0.0394 (12) | |
H33 | −0.1417 | 0.3655 | 0.8550 | 0.047* | |
C34 | −0.0343 (3) | 0.2387 (8) | 0.9182 (3) | 0.0403 (12) | |
H34 | 0.0033 | 0.2705 | 0.9655 | 0.048* | |
C35 | 0.0280 (4) | 0.1894 (8) | 0.8546 (4) | 0.0560 (15) | |
H35A | 0.0722 | 0.0924 | 0.8731 | 0.067* | |
H35B | −0.0086 | 0.1352 | 0.8111 | 0.067* | |
O10 | 0.7960 (3) | 0.0174 (9) | 0.0551 (3) | 0.0493 (17) | 0.691 (7) |
H10 | 0.8335 | −0.0306 | 0.0896 | 0.074* | 0.691 (7) |
C36 | 0.7549 (9) | 0.1927 (18) | 0.0845 (8) | 0.125 (5) | 0.691 (7) |
H36A | 0.7459 | 0.1779 | 0.1389 | 0.187* | 0.691 (7) |
H36B | 0.6964 | 0.2157 | 0.0571 | 0.187* | 0.691 (7) |
H36C | 0.7953 | 0.3000 | 0.0770 | 0.187* | 0.691 (7) |
O10' | 0.6922 (8) | 0.335 (2) | 0.0543 (8) | 0.061 (4) | 0.309 (7) |
H10' | 0.7417 | 0.3130 | 0.0354 | 0.092* | 0.309 (7) |
C36' | 0.7061 (14) | 0.464 (3) | 0.1179 (10) | 0.073 (5) | 0.309 (7) |
H36D | 0.7699 | 0.5021 | 0.1227 | 0.110* | 0.309 (7) |
H36E | 0.6900 | 0.4010 | 0.1647 | 0.110* | 0.309 (7) |
H36F | 0.6680 | 0.5760 | 0.1091 | 0.110* | 0.309 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0522 (19) | 0.0346 (19) | 0.0344 (18) | −0.0096 (16) | 0.0020 (15) | −0.0026 (15) |
O2 | 0.060 (2) | 0.052 (2) | 0.047 (2) | 0.024 (2) | 0.0054 (19) | 0.013 (2) |
O3 | 0.0486 (18) | 0.039 (2) | 0.043 (2) | −0.0094 (17) | 0.0025 (16) | −0.0010 (17) |
O4 | 0.0370 (16) | 0.044 (2) | 0.0363 (18) | −0.0099 (16) | 0.0004 (14) | 0.0083 (16) |
O5 | 0.056 (2) | 0.056 (3) | 0.053 (2) | −0.014 (2) | −0.0114 (18) | 0.016 (2) |
O6 | 0.056 (2) | 0.039 (2) | 0.057 (2) | 0.0103 (19) | −0.0012 (18) | 0.0039 (19) |
O7 | 0.072 (3) | 0.065 (3) | 0.054 (2) | 0.020 (2) | 0.031 (2) | 0.010 (2) |
O8 | 0.077 (3) | 0.037 (2) | 0.062 (3) | −0.002 (2) | 0.021 (2) | 0.003 (2) |
O9 | 0.0485 (19) | 0.045 (2) | 0.056 (2) | 0.0113 (18) | 0.0118 (18) | 0.0088 (19) |
C1 | 0.073 (4) | 0.029 (3) | 0.055 (3) | 0.002 (3) | 0.020 (3) | 0.002 (3) |
C2 | 0.093 (4) | 0.030 (3) | 0.050 (3) | 0.013 (3) | 0.024 (3) | 0.012 (3) |
C3 | 0.054 (3) | 0.032 (3) | 0.035 (3) | −0.009 (2) | 0.008 (2) | −0.006 (2) |
C4 | 0.042 (2) | 0.031 (3) | 0.036 (3) | 0.001 (2) | 0.003 (2) | −0.003 (2) |
C5 | 0.040 (2) | 0.025 (2) | 0.043 (3) | −0.002 (2) | 0.000 (2) | −0.004 (2) |
C6 | 0.053 (3) | 0.039 (3) | 0.060 (3) | 0.018 (3) | 0.016 (3) | 0.012 (3) |
C7 | 0.047 (3) | 0.059 (4) | 0.044 (3) | 0.019 (3) | 0.007 (2) | 0.018 (3) |
C8 | 0.032 (2) | 0.033 (3) | 0.039 (3) | 0.003 (2) | −0.005 (2) | −0.003 (2) |
C9 | 0.035 (2) | 0.027 (2) | 0.039 (3) | 0.004 (2) | −0.004 (2) | 0.000 (2) |
C10 | 0.041 (2) | 0.024 (2) | 0.039 (3) | 0.001 (2) | 0.000 (2) | −0.001 (2) |
C11 | 0.053 (3) | 0.028 (2) | 0.041 (3) | 0.010 (2) | 0.003 (2) | 0.007 (2) |
C12 | 0.050 (3) | 0.033 (3) | 0.047 (3) | 0.010 (2) | 0.002 (2) | −0.001 (2) |
C13 | 0.031 (2) | 0.033 (3) | 0.037 (3) | 0.003 (2) | −0.006 (2) | −0.002 (2) |
C14 | 0.034 (2) | 0.032 (2) | 0.028 (2) | 0.001 (2) | −0.0039 (19) | 0.000 (2) |
C15 | 0.045 (3) | 0.030 (3) | 0.037 (3) | 0.004 (2) | −0.001 (2) | 0.001 (2) |
C16 | 0.037 (2) | 0.035 (3) | 0.028 (2) | −0.003 (2) | −0.0035 (19) | −0.001 (2) |
C17 | 0.032 (2) | 0.041 (3) | 0.036 (3) | 0.001 (2) | −0.002 (2) | −0.003 (2) |
C18 | 0.039 (2) | 0.056 (3) | 0.042 (3) | −0.004 (3) | −0.007 (2) | −0.002 (3) |
C19 | 0.042 (2) | 0.035 (3) | 0.039 (3) | 0.007 (2) | −0.008 (2) | −0.001 (2) |
C20 | 0.035 (2) | 0.058 (4) | 0.045 (3) | 0.003 (3) | −0.001 (2) | 0.000 (3) |
C21 | 0.050 (3) | 0.065 (5) | 0.079 (5) | 0.016 (3) | 0.003 (3) | 0.006 (4) |
C22 | 0.040 (3) | 0.068 (4) | 0.062 (4) | 0.005 (3) | 0.010 (3) | 0.007 (3) |
C23 | 0.043 (3) | 0.047 (3) | 0.046 (3) | −0.009 (2) | 0.007 (2) | 0.003 (3) |
C24 | 0.039 (2) | 0.038 (3) | 0.039 (3) | −0.008 (2) | 0.007 (2) | 0.004 (2) |
C25 | 0.043 (3) | 0.040 (3) | 0.040 (3) | −0.007 (2) | 0.003 (2) | 0.002 (2) |
C26 | 0.063 (4) | 0.070 (4) | 0.074 (4) | −0.004 (4) | 0.019 (3) | 0.026 (4) |
C27 | 0.077 (4) | 0.046 (3) | 0.063 (4) | 0.009 (3) | 0.000 (3) | −0.001 (3) |
C28 | 0.038 (2) | 0.049 (3) | 0.039 (3) | −0.006 (2) | −0.009 (2) | 0.001 (2) |
C29 | 0.061 (3) | 0.033 (3) | 0.051 (3) | −0.006 (3) | 0.011 (3) | −0.008 (3) |
C30 | 0.054 (3) | 0.054 (4) | 0.055 (3) | 0.013 (3) | 0.008 (3) | −0.002 (3) |
C31 | 0.041 (2) | 0.035 (3) | 0.036 (3) | −0.005 (2) | −0.003 (2) | 0.001 (2) |
C32 | 0.038 (2) | 0.035 (3) | 0.036 (3) | 0.006 (2) | −0.005 (2) | 0.001 (2) |
C33 | 0.043 (3) | 0.042 (3) | 0.033 (3) | 0.005 (2) | 0.003 (2) | 0.000 (2) |
C34 | 0.048 (3) | 0.038 (3) | 0.035 (3) | −0.002 (2) | 0.002 (2) | 0.001 (2) |
C35 | 0.075 (4) | 0.035 (3) | 0.061 (4) | 0.010 (3) | 0.028 (3) | 0.009 (3) |
O10 | 0.040 (3) | 0.067 (4) | 0.040 (3) | −0.004 (3) | −0.007 (2) | −0.013 (3) |
C36 | 0.104 (8) | 0.174 (12) | 0.095 (8) | −0.041 (9) | −0.003 (7) | 0.015 (9) |
O10' | 0.040 (6) | 0.084 (9) | 0.059 (7) | −0.011 (7) | −0.005 (5) | 0.036 (7) |
C36' | 0.062 (9) | 0.103 (12) | 0.054 (10) | −0.023 (10) | −0.006 (8) | 0.026 (10) |
Geometric parameters (Å, º) top
O1—C31 | 1.375 (6) | C16—C17 | 1.540 (7) |
O1—C3 | 1.449 (6) | C17—C20 | 1.550 (6) |
O2—C15 | 1.413 (6) | C17—H17 | 0.9800 |
O2—H2 | 0.8200 | C18—H18A | 0.9600 |
O3—C16 | 1.420 (6) | C18—H18B | 0.9600 |
O3—C23 | 1.435 (6) | C18—H18C | 0.9600 |
O4—C16 | 1.438 (5) | C19—H19A | 0.9700 |
O4—C24 | 1.443 (6) | C19—H19B | 0.9700 |
O5—C25 | 1.431 (6) | C20—C21 | 1.528 (9) |
O5—H5 | 0.8200 | C20—C22 | 1.541 (8) |
O6—C32 | 1.418 (6) | C20—H20 | 0.9800 |
O6—H6 | 0.8200 | C21—H21A | 0.9600 |
O7—C33 | 1.418 (6) | C21—H21B | 0.9600 |
O7—H7 | 0.8200 | C21—H21C | 0.9600 |
O8—C34 | 1.425 (7) | C22—C23 | 1.522 (8) |
O8—H8 | 0.8200 | C22—H22A | 0.9700 |
O9—C31 | 1.437 (6) | C22—H22B | 0.9700 |
O9—C35 | 1.441 (7) | C23—C24 | 1.547 (7) |
C1—C10 | 1.515 (7) | C23—H23 | 0.9800 |
C1—C2 | 1.540 (7) | C24—C25 | 1.543 (7) |
C1—H1A | 0.9700 | C24—H24 | 0.9800 |
C1—H1B | 0.9700 | C25—C27 | 1.496 (8) |
C2—C3 | 1.519 (8) | C25—C26 | 1.528 (8) |
C2—H2A | 0.9700 | C26—H26A | 0.9600 |
C2—H2B | 0.9700 | C26—H26B | 0.9600 |
C3—C4 | 1.542 (7) | C26—H26C | 0.9600 |
C3—H3 | 0.9800 | C27—H27A | 0.9600 |
C4—C29 | 1.531 (7) | C27—H27B | 0.9600 |
C4—C30 | 1.544 (7) | C27—H27C | 0.9600 |
C4—C5 | 1.563 (7) | C28—H28A | 0.9600 |
C5—C10 | 1.514 (6) | C28—H28B | 0.9600 |
C5—C6 | 1.521 (7) | C28—H28C | 0.9600 |
C5—H5A | 0.9800 | C29—H29A | 0.9600 |
C6—C7 | 1.537 (7) | C29—H29B | 0.9600 |
C6—H6A | 0.9700 | C29—H29C | 0.9600 |
C6—H6B | 0.9700 | C30—H30A | 0.9600 |
C7—C8 | 1.521 (6) | C30—H30B | 0.9600 |
C7—H7A | 0.9700 | C30—H30C | 0.9600 |
C7—H7B | 0.9700 | C31—C32 | 1.521 (7) |
C8—C14 | 1.538 (6) | C31—H31 | 0.9800 |
C8—C9 | 1.551 (7) | C32—C33 | 1.529 (7) |
C8—H8A | 0.9800 | C32—H32 | 0.9800 |
C9—C19 | 1.496 (7) | C33—C34 | 1.513 (7) |
C9—C10 | 1.531 (7) | C33—H33 | 0.9800 |
C9—C11 | 1.540 (7) | C34—C35 | 1.501 (7) |
C10—C19 | 1.503 (6) | C34—H34 | 0.9800 |
C11—C12 | 1.544 (7) | C35—H35A | 0.9700 |
C11—H11A | 0.9700 | C35—H35B | 0.9700 |
C11—H11B | 0.9700 | O10—C36 | 1.458 (9) |
C12—C13 | 1.542 (7) | O10—H10 | 0.8503 |
C12—H12A | 0.9700 | C36—H36A | 0.9600 |
C12—H12B | 0.9700 | C36—H36B | 0.9600 |
C13—C18 | 1.543 (7) | C36—H36C | 0.9600 |
C13—C14 | 1.553 (6) | O10'—C36' | 1.423 (10) |
C13—C17 | 1.557 (7) | O10'—H10' | 0.8200 |
C14—C28 | 1.530 (6) | C36'—H36D | 0.9600 |
C14—C15 | 1.537 (7) | C36'—H36E | 0.9600 |
C15—C16 | 1.535 (7) | C36'—H36F | 0.9600 |
C15—H15 | 0.9800 | | |
| | | |
C31—O1—C3 | 116.3 (4) | C13—C18—H18C | 109.5 |
C15—O2—H2 | 109.5 | H18A—C18—H18C | 109.5 |
C16—O3—C23 | 101.2 (4) | H18B—C18—H18C | 109.5 |
C16—O4—C24 | 107.3 (3) | C9—C19—C10 | 61.4 (3) |
C25—O5—H5 | 109.5 | C9—C19—H19A | 117.6 |
C32—O6—H6 | 109.5 | C10—C19—H19A | 117.6 |
C33—O7—H7 | 109.5 | C9—C19—H19B | 117.6 |
C34—O8—H8 | 109.5 | C10—C19—H19B | 117.6 |
C31—O9—C35 | 112.4 (4) | H19A—C19—H19B | 114.7 |
C10—C1—C2 | 109.6 (4) | C21—C20—C22 | 111.3 (5) |
C10—C1—H1A | 109.8 | C21—C20—C17 | 113.7 (5) |
C2—C1—H1A | 109.8 | C22—C20—C17 | 108.7 (4) |
C10—C1—H1B | 109.8 | C21—C20—H20 | 107.6 |
C2—C1—H1B | 109.8 | C22—C20—H20 | 107.6 |
H1A—C1—H1B | 108.2 | C17—C20—H20 | 107.6 |
C3—C2—C1 | 111.0 (5) | C20—C21—H21A | 109.5 |
C3—C2—H2A | 109.4 | C20—C21—H21B | 109.5 |
C1—C2—H2A | 109.4 | H21A—C21—H21B | 109.5 |
C3—C2—H2B | 109.4 | C20—C21—H21C | 109.5 |
C1—C2—H2B | 109.4 | H21A—C21—H21C | 109.5 |
H2A—C2—H2B | 108.0 | H21B—C21—H21C | 109.5 |
O1—C3—C2 | 110.7 (4) | C23—C22—C20 | 111.8 (5) |
O1—C3—C4 | 108.1 (4) | C23—C22—H22A | 109.3 |
C2—C3—C4 | 113.1 (4) | C20—C22—H22A | 109.3 |
O1—C3—H3 | 108.3 | C23—C22—H22B | 109.3 |
C2—C3—H3 | 108.3 | C20—C22—H22B | 109.3 |
C4—C3—H3 | 108.3 | H22A—C22—H22B | 107.9 |
C29—C4—C3 | 109.7 (4) | O3—C23—C22 | 110.1 (4) |
C29—C4—C30 | 110.0 (4) | O3—C23—C24 | 101.2 (4) |
C3—C4—C30 | 108.3 (4) | C22—C23—C24 | 112.6 (5) |
C29—C4—C5 | 112.1 (4) | O3—C23—H23 | 110.8 |
C3—C4—C5 | 107.2 (4) | C22—C23—H23 | 110.8 |
C30—C4—C5 | 109.5 (4) | C24—C23—H23 | 110.8 |
C10—C5—C6 | 113.7 (4) | O4—C24—C25 | 111.2 (4) |
C10—C5—C4 | 113.0 (4) | O4—C24—C23 | 102.4 (4) |
C6—C5—C4 | 113.8 (4) | C25—C24—C23 | 115.0 (4) |
C10—C5—H5A | 105.1 | O4—C24—H24 | 109.3 |
C6—C5—H5A | 105.1 | C25—C24—H24 | 109.3 |
C4—C5—H5A | 105.1 | C23—C24—H24 | 109.3 |
C5—C6—C7 | 110.1 (5) | O5—C25—C27 | 109.2 (5) |
C5—C6—H6A | 109.6 | O5—C25—C26 | 106.9 (5) |
C7—C6—H6A | 109.6 | C27—C25—C26 | 112.1 (5) |
C5—C6—H6B | 109.6 | O5—C25—C24 | 105.0 (4) |
C7—C6—H6B | 109.6 | C27—C25—C24 | 114.5 (4) |
H6A—C6—H6B | 108.2 | C26—C25—C24 | 108.7 (4) |
C8—C7—C6 | 109.4 (4) | C25—C26—H26A | 109.5 |
C8—C7—H7A | 109.8 | C25—C26—H26B | 109.5 |
C6—C7—H7A | 109.8 | H26A—C26—H26B | 109.5 |
C8—C7—H7B | 109.8 | C25—C26—H26C | 109.5 |
C6—C7—H7B | 109.8 | H26A—C26—H26C | 109.5 |
H7A—C7—H7B | 108.2 | H26B—C26—H26C | 109.5 |
C7—C8—C14 | 114.2 (4) | C25—C27—H27A | 109.5 |
C7—C8—C9 | 112.0 (4) | C25—C27—H27B | 109.5 |
C14—C8—C9 | 112.6 (4) | H27A—C27—H27B | 109.5 |
C7—C8—H8A | 105.7 | C25—C27—H27C | 109.5 |
C14—C8—H8A | 105.7 | H27A—C27—H27C | 109.5 |
C9—C8—H8A | 105.7 | H27B—C27—H27C | 109.5 |
C19—C9—C10 | 59.5 (3) | C14—C28—H28A | 109.5 |
C19—C9—C11 | 120.6 (4) | C14—C28—H28B | 109.5 |
C10—C9—C11 | 118.1 (4) | H28A—C28—H28B | 109.5 |
C19—C9—C8 | 113.8 (4) | C14—C28—H28C | 109.5 |
C10—C9—C8 | 117.3 (4) | H28A—C28—H28C | 109.5 |
C11—C9—C8 | 115.9 (4) | H28B—C28—H28C | 109.5 |
C19—C10—C5 | 123.6 (4) | C4—C29—H29A | 109.5 |
C19—C10—C1 | 115.0 (4) | C4—C29—H29B | 109.5 |
C5—C10—C1 | 109.8 (4) | H29A—C29—H29B | 109.5 |
C19—C10—C9 | 59.1 (3) | C4—C29—H29C | 109.5 |
C5—C10—C9 | 120.7 (4) | H29A—C29—H29C | 109.5 |
C1—C10—C9 | 120.7 (4) | H29B—C29—H29C | 109.5 |
C9—C11—C12 | 116.8 (4) | C4—C30—H30A | 109.5 |
C9—C11—H11A | 108.1 | C4—C30—H30B | 109.5 |
C12—C11—H11A | 108.1 | H30A—C30—H30B | 109.5 |
C9—C11—H11B | 108.1 | C4—C30—H30C | 109.5 |
C12—C11—H11B | 108.1 | H30A—C30—H30C | 109.5 |
H11A—C11—H11B | 107.3 | H30B—C30—H30C | 109.5 |
C13—C12—C11 | 113.6 (4) | O1—C31—O9 | 108.1 (4) |
C13—C12—H12A | 108.9 | O1—C31—C32 | 111.4 (4) |
C11—C12—H12A | 108.9 | O9—C31—C32 | 108.2 (4) |
C13—C12—H12B | 108.9 | O1—C31—H31 | 109.7 |
C11—C12—H12B | 108.9 | O9—C31—H31 | 109.7 |
H12A—C12—H12B | 107.7 | C32—C31—H31 | 109.7 |
C12—C13—C18 | 107.6 (4) | O6—C32—C31 | 109.6 (4) |
C12—C13—C14 | 108.1 (4) | O6—C32—C33 | 109.2 (4) |
C18—C13—C14 | 113.1 (4) | C31—C32—C33 | 109.5 (4) |
C12—C13—C17 | 115.9 (4) | O6—C32—H32 | 109.6 |
C18—C13—C17 | 110.4 (4) | C31—C32—H32 | 109.6 |
C14—C13—C17 | 101.9 (3) | C33—C32—H32 | 109.6 |
C28—C14—C15 | 108.7 (4) | O7—C33—C34 | 108.4 (4) |
C28—C14—C8 | 111.4 (4) | O7—C33—C32 | 111.0 (4) |
C15—C14—C8 | 113.5 (4) | C34—C33—C32 | 111.8 (4) |
C28—C14—C13 | 112.1 (4) | O7—C33—H33 | 108.5 |
C15—C14—C13 | 100.5 (4) | C34—C33—H33 | 108.5 |
C8—C14—C13 | 110.2 (3) | C32—C33—H33 | 108.5 |
O2—C15—C16 | 115.1 (4) | O8—C34—C35 | 105.4 (4) |
O2—C15—C14 | 117.8 (4) | O8—C34—C33 | 112.0 (4) |
C16—C15—C14 | 104.3 (4) | C35—C34—C33 | 111.0 (4) |
O2—C15—H15 | 106.2 | O8—C34—H34 | 109.4 |
C16—C15—H15 | 106.2 | C35—C34—H34 | 109.4 |
C14—C15—H15 | 106.2 | C33—C34—H34 | 109.4 |
O3—C16—O4 | 103.8 (3) | O9—C35—C34 | 111.8 (5) |
O3—C16—C15 | 112.4 (4) | O9—C35—H35A | 109.3 |
O4—C16—C15 | 110.9 (4) | C34—C35—H35A | 109.3 |
O3—C16—C17 | 110.8 (3) | O9—C35—H35B | 109.3 |
O4—C16—C17 | 112.4 (4) | C34—C35—H35B | 109.3 |
C15—C16—C17 | 106.6 (4) | H35A—C35—H35B | 107.9 |
C16—C17—C20 | 110.3 (4) | C36—O10—H10 | 109.9 |
C16—C17—C13 | 104.3 (4) | C36'—O10'—H10' | 109.5 |
C20—C17—C13 | 118.3 (4) | O10'—C36'—H36D | 109.5 |
C16—C17—H17 | 107.8 | O10'—C36'—H36E | 109.5 |
C20—C17—H17 | 107.8 | H36D—C36'—H36E | 109.5 |
C13—C17—H17 | 107.8 | O10'—C36'—H36F | 109.5 |
C13—C18—H18A | 109.5 | H36D—C36'—H36F | 109.5 |
C13—C18—H18B | 109.5 | H36E—C36'—H36F | 109.5 |
H18A—C18—H18B | 109.5 | | |
| | | |
C10—C1—C2—C3 | 57.7 (7) | C8—C14—C15—C16 | 159.1 (3) |
C31—O1—C3—C2 | −88.0 (5) | C13—C14—C15—C16 | 41.4 (4) |
C31—O1—C3—C4 | 147.7 (4) | C23—O3—C16—O4 | −47.1 (4) |
C1—C2—C3—O1 | −178.1 (4) | C23—O3—C16—C15 | −167.1 (4) |
C1—C2—C3—C4 | −56.7 (6) | C23—O3—C16—C17 | 73.8 (4) |
O1—C3—C4—C29 | 54.5 (5) | C24—O4—C16—O3 | 28.2 (5) |
C2—C3—C4—C29 | −68.3 (5) | C24—O4—C16—C15 | 149.1 (4) |
O1—C3—C4—C30 | −65.5 (5) | C24—O4—C16—C17 | −91.6 (4) |
C2—C3—C4—C30 | 171.6 (4) | O2—C15—C16—O3 | 87.4 (5) |
O1—C3—C4—C5 | 176.5 (4) | C14—C15—C16—O3 | −141.9 (4) |
C2—C3—C4—C5 | 53.6 (5) | O2—C15—C16—O4 | −28.3 (6) |
C29—C4—C5—C10 | 64.9 (5) | C14—C15—C16—O4 | 102.4 (4) |
C3—C4—C5—C10 | −55.5 (5) | O2—C15—C16—C17 | −151.1 (4) |
C30—C4—C5—C10 | −172.7 (4) | C14—C15—C16—C17 | −20.4 (5) |
C29—C4—C5—C6 | −66.7 (6) | O3—C16—C17—C20 | −14.4 (5) |
C3—C4—C5—C6 | 172.9 (4) | O4—C16—C17—C20 | 101.3 (4) |
C30—C4—C5—C6 | 55.6 (6) | C15—C16—C17—C20 | −136.9 (4) |
C10—C5—C6—C7 | 48.7 (6) | O3—C16—C17—C13 | 113.6 (4) |
C4—C5—C6—C7 | −180.0 (4) | O4—C16—C17—C13 | −130.7 (4) |
C5—C6—C7—C8 | −68.2 (6) | C15—C16—C17—C13 | −8.9 (5) |
C6—C7—C8—C14 | −174.0 (4) | C12—C13—C17—C16 | 151.5 (4) |
C6—C7—C8—C9 | 56.5 (6) | C18—C13—C17—C16 | −85.9 (4) |
C7—C8—C9—C19 | −94.8 (5) | C14—C13—C17—C16 | 34.5 (4) |
C14—C8—C9—C19 | 134.9 (4) | C12—C13—C17—C20 | −85.5 (6) |
C7—C8—C9—C10 | −28.1 (6) | C18—C13—C17—C20 | 37.0 (6) |
C14—C8—C9—C10 | −158.5 (4) | C14—C13—C17—C20 | 157.4 (5) |
C7—C8—C9—C11 | 119.0 (5) | C11—C9—C19—C10 | −106.6 (5) |
C14—C8—C9—C11 | −11.4 (6) | C8—C9—C19—C10 | 108.8 (4) |
C6—C5—C10—C19 | 50.3 (6) | C5—C10—C19—C9 | −108.4 (5) |
C4—C5—C10—C19 | −81.4 (6) | C1—C10—C19—C9 | 112.1 (5) |
C6—C5—C10—C1 | −168.4 (5) | C16—C17—C20—C21 | −168.1 (5) |
C4—C5—C10—C1 | 59.9 (5) | C13—C17—C20—C21 | 72.0 (6) |
C6—C5—C10—C9 | −20.9 (6) | C16—C17—C20—C22 | −43.5 (6) |
C4—C5—C10—C9 | −152.6 (4) | C13—C17—C20—C22 | −163.4 (5) |
C2—C1—C10—C19 | 86.0 (6) | C21—C20—C22—C23 | 170.4 (5) |
C2—C1—C10—C5 | −58.9 (6) | C17—C20—C22—C23 | 44.4 (7) |
C2—C1—C10—C9 | 153.6 (4) | C16—O3—C23—C22 | −72.9 (4) |
C11—C9—C10—C19 | 110.8 (5) | C16—O3—C23—C24 | 46.4 (4) |
C8—C9—C10—C19 | −102.8 (5) | C20—C22—C23—O3 | 13.0 (6) |
C19—C9—C10—C5 | 113.3 (5) | C20—C22—C23—C24 | −99.2 (6) |
C11—C9—C10—C5 | −135.9 (4) | C16—O4—C24—C25 | −122.5 (4) |
C8—C9—C10—C5 | 10.5 (6) | C16—O4—C24—C23 | 0.9 (5) |
C19—C9—C10—C1 | −102.6 (5) | O3—C23—C24—O4 | −29.0 (5) |
C11—C9—C10—C1 | 8.1 (7) | C22—C23—C24—O4 | 88.6 (5) |
C8—C9—C10—C1 | 154.5 (5) | O3—C23—C24—C25 | 91.8 (5) |
C19—C9—C11—C12 | −103.2 (5) | C22—C23—C24—C25 | −150.7 (5) |
C10—C9—C11—C12 | −172.5 (4) | O4—C24—C25—O5 | −63.5 (5) |
C8—C9—C11—C12 | 40.6 (6) | C23—C24—C25—O5 | −179.2 (4) |
C9—C11—C12—C13 | −12.5 (6) | O4—C24—C25—C27 | 56.3 (6) |
C11—C12—C13—C18 | 81.8 (5) | C23—C24—C25—C27 | −59.5 (6) |
C11—C12—C13—C14 | −40.7 (6) | O4—C24—C25—C26 | −177.6 (5) |
C11—C12—C13—C17 | −154.2 (4) | C23—C24—C25—C26 | 66.7 (6) |
C7—C8—C14—C28 | −46.9 (6) | C3—O1—C31—O9 | 90.5 (5) |
C9—C8—C14—C28 | 82.3 (5) | C3—O1—C31—C32 | −150.7 (4) |
C7—C8—C14—C15 | 76.2 (5) | C35—O9—C31—O1 | −175.3 (4) |
C9—C8—C14—C15 | −154.6 (4) | C35—O9—C31—C32 | 63.9 (5) |
C7—C8—C14—C13 | −172.0 (4) | O1—C31—C32—O6 | 62.3 (5) |
C9—C8—C14—C13 | −42.8 (5) | O9—C31—C32—O6 | −179.0 (4) |
C12—C13—C14—C28 | −53.9 (5) | O1—C31—C32—C33 | −178.1 (4) |
C18—C13—C14—C28 | −172.9 (4) | O9—C31—C32—C33 | −59.4 (5) |
C17—C13—C14—C28 | 68.7 (5) | O6—C32—C33—O7 | −65.5 (5) |
C12—C13—C14—C15 | −169.2 (4) | C31—C32—C33—O7 | 174.6 (4) |
C18—C13—C14—C15 | 71.7 (5) | O6—C32—C33—C34 | 173.3 (4) |
C17—C13—C14—C15 | −46.7 (4) | C31—C32—C33—C34 | 53.4 (5) |
C12—C13—C14—C8 | 70.8 (5) | O7—C33—C34—O8 | 70.7 (5) |
C18—C13—C14—C8 | −48.3 (5) | C32—C33—C34—O8 | −166.6 (4) |
C17—C13—C14—C8 | −166.7 (4) | O7—C33—C34—C35 | −171.8 (5) |
C28—C14—C15—O2 | 52.7 (5) | C32—C33—C34—C35 | −49.1 (6) |
C8—C14—C15—O2 | −71.8 (5) | C31—O9—C35—C34 | −60.5 (6) |
C13—C14—C15—O2 | 170.5 (4) | O8—C34—C35—O9 | 172.9 (5) |
C28—C14—C15—C16 | −76.4 (5) | C33—C34—C35—O9 | 51.4 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O6i | 0.82 | 2.19 | 2.880 (5) | 143 |
O2—H2···O4 | 0.82 | 2.32 | 2.726 (5) | 111 |
O5—H5···O10ii | 0.82 | 2.02 | 2.841 (7) | 175 |
O6—H6···O8iii | 0.82 | 2.11 | 2.916 (6) | 168 |
O7—H7···O5iv | 0.82 | 2.01 | 2.727 (6) | 146 |
O8—H8···O10v | 0.82 | 2.07 | 2.846 (6) | 159 |
O10—H10···O9vi | 0.85 | 2.02 | 2.867 (6) | 180 |
O10′—H10′···O7vii | 0.82 | 2.40 | 3.087 (13) | 142 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x+1, y+3/2, −z; (iii) x, y+1, z; (iv) −x, y−1/2, −z+1; (v) x−1, y, z+1; (vi) −x+1, y−1/2, −z+1; (vii) x+1, y, z−1. |