The title compound, C
29H
44O
6·CH
4O, namely suberoretisteroid A methanol solvate, is a fused hexacyclic steroid which was isolated from the South China Sea gorgonian
Suberogorgia reticulata. There are two independent molecules in the asymmetric unit. Suberoretisteroid A molecules and methanol solvent molecules are linked
via intermolecular O—H
O hydrogen bonds to form two independent two-dimensional frameworks.
Supporting information
CCDC reference: 238944
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.013 Å
- R factor = 0.071
- wR factor = 0.173
- Data-to-parameter ratio = 8.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 36 Perc.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 13
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.738 0.980
Tmin(prime) and Tmax expected: 0.965 0.984
RR(prime) = 0.767
Please check that your absorption correction is appropriate.
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 0.769
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.150
SHFSU01_ALERT_2_C The absolute value of parameter shift to su ratio > 0.05
Absolute value of the parameter shift to su ratio given 0.090
Additional refinement cycles may be required.
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.77
PLAT080_ALERT_2_C Maximum Shift/Error ............................ 0.09
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT213_ALERT_2_C Atom C44 has ADP max/min Ratio ............. 3.70 prolat
PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C19 .. 5.35 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C39
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C54
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.18
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.18
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 42.00 A 3
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 25.50
From the CIF: _reflns_number_total 5608
Count of symmetry unique reflns 5649
Completeness (_total/calc) 99.27%
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
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
19 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
13 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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 and PLATON (Spek, 2003).
(3
S*,16
S*,20
R*,22
R*,24
S*)-3,22,25-Trihydroxy-16,24:20,24-diepoxycholest- 5-en-3-yl acetate methanol solvate
top
Crystal data top
C29H44O6·CH4O | F(000) = 1136 |
Mr = 520.68 | Dx = 1.171 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 946 reflections |
a = 8.6596 (17) Å | θ = 4.9–33.2° |
b = 22.247 (4) Å | µ = 0.08 mm−1 |
c = 15.891 (3) Å | T = 293 K |
β = 105.314 (3)° | Block, colorless |
V = 2952.7 (10) Å3 | 0.42 × 0.21 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD diffractometer | 5608 independent reflections |
Radiation source: fine-focus sealed tube | 2037 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.150 |
φ and ω scans | θmax = 25.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.738, Tmax = 0.980 | k = −26→26 |
15224 measured reflections | l = −19→14 |
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)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 0.77 | w = 1/[σ2(Fo2) + (0.0481P)2] where P = (Fo2 + 2Fc2)/3 |
5608 reflections | (Δ/σ)max = 0.090 |
688 parameters | Δρmax = 0.25 e Å−3 |
1 restraint | Δρmin = −0.27 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 | −0.4001 (7) | 0.5089 (3) | 0.0273 (4) | 0.0554 (18) | |
O2 | −0.3176 (9) | 0.4521 (4) | −0.0679 (4) | 0.075 (2) | |
O3 | 0.7014 (7) | 0.4619 (3) | 0.5906 (4) | 0.0519 (18) | |
O4 | 0.5882 (7) | 0.4443 (3) | 0.7048 (3) | 0.0497 (17) | |
O5 | 0.6271 (11) | 0.2942 (3) | 0.6367 (5) | 0.081 (2) | |
H5 | 0.5887 | 0.2657 | 0.6569 | 0.121* | |
O6 | 0.8714 (9) | 0.4800 (4) | 0.8229 (4) | 0.076 (2) | |
H6 | 0.8191 | 0.4505 | 0.8296 | 0.115* | |
O7 | −0.1029 (7) | 0.2022 (3) | 0.6421 (3) | 0.0514 (18) | |
O8 | 0.0906 (9) | 0.2554 (4) | 0.7336 (4) | 0.090 (3) | |
O9 | 0.4458 (7) | 0.2556 (3) | 0.0763 (3) | 0.0472 (17) | |
O10 | 0.2228 (7) | 0.2713 (3) | −0.0382 (3) | 0.0428 (15) | |
O11 | 0.3244 (9) | 0.4226 (3) | 0.0287 (4) | 0.067 (2) | |
H11 | 0.2892 | 0.4536 | 0.0026 | 0.100* | |
O12 | 0.3941 (8) | 0.2373 (4) | −0.1555 (3) | 0.069 (2) | |
H12 | 0.3468 | 0.2696 | −0.1613 | 0.103* | |
O13 | 0.5034 (11) | 0.1997 (4) | 0.7086 (5) | 0.089 (3) | |
H13 | 0.5430 | 0.2085 | 0.7599 | 0.133* | |
O14 | 0.1163 (10) | 0.5136 (3) | 0.9556 (4) | 0.078 (2) | |
H14A | 0.0845 | 0.5059 | 0.9035 | 0.117* | |
C1 | −0.2224 (11) | 0.4545 (5) | 0.2549 (5) | 0.052 (3) | |
H1A | −0.2672 | 0.4523 | 0.3047 | 0.063* | |
H1B | −0.1993 | 0.4138 | 0.2401 | 0.063* | |
C2 | −0.3510 (11) | 0.4821 (5) | 0.1761 (5) | 0.054 (3) | |
H2A | −0.4484 | 0.4584 | 0.1637 | 0.064* | |
H2B | −0.3764 | 0.5229 | 0.1893 | 0.064* | |
C3 | −0.2811 (11) | 0.4816 (5) | 0.0990 (5) | 0.048 (3) | |
H3 | −0.2594 | 0.4402 | 0.0842 | 0.058* | |
C4 | −0.1310 (11) | 0.5185 (4) | 0.1163 (5) | 0.046 (2) | |
H4A | −0.1580 | 0.5604 | 0.1217 | 0.055* | |
H4B | −0.0860 | 0.5151 | 0.0667 | 0.055* | |
C5 | −0.0062 (12) | 0.4998 (4) | 0.1975 (6) | 0.048 (3) | |
C6 | 0.1429 (12) | 0.4882 (4) | 0.1972 (5) | 0.051 (3) | |
H6A | 0.1673 | 0.4911 | 0.1437 | 0.061* | |
C7 | 0.2726 (11) | 0.4716 (5) | 0.2717 (5) | 0.054 (3) | |
H7A | 0.3646 | 0.4966 | 0.2721 | 0.065* | |
H7B | 0.3023 | 0.4303 | 0.2644 | 0.065* | |
C8 | 0.2357 (10) | 0.4773 (4) | 0.3601 (5) | 0.042 (2) | |
H8 | 0.2440 | 0.5194 | 0.3790 | 0.050* | |
C9 | 0.0583 (11) | 0.4540 (4) | 0.3466 (5) | 0.042 (2) | |
H9 | 0.0553 | 0.4132 | 0.3229 | 0.050* | |
C10 | −0.0656 (11) | 0.4897 (4) | 0.2814 (5) | 0.037 (2) | |
C11 | 0.0199 (12) | 0.4480 (5) | 0.4370 (5) | 0.056 (3) | |
H11A | 0.0089 | 0.4878 | 0.4594 | 0.067* | |
H11B | −0.0819 | 0.4275 | 0.4289 | 0.067* | |
C12 | 0.1489 (12) | 0.4133 (4) | 0.5046 (6) | 0.057 (3) | |
H12A | 0.1193 | 0.4127 | 0.5594 | 0.068* | |
H12B | 0.1506 | 0.3721 | 0.4851 | 0.068* | |
C13 | 0.3157 (11) | 0.4391 (4) | 0.5209 (5) | 0.041 (2) | |
C14 | 0.3449 (11) | 0.4393 (5) | 0.4269 (5) | 0.047 (3) | |
H14 | 0.3326 | 0.3978 | 0.4054 | 0.056* | |
C15 | 0.5273 (12) | 0.4556 (6) | 0.4467 (5) | 0.071 (3) | |
H15A | 0.5447 | 0.4985 | 0.4549 | 0.085* | |
H15B | 0.5729 | 0.4419 | 0.4004 | 0.085* | |
C16 | 0.5994 (12) | 0.4197 (5) | 0.5346 (6) | 0.063 (3) | |
H16 | 0.6624 | 0.3854 | 0.5235 | 0.076* | |
C17 | 0.4585 (11) | 0.3975 (4) | 0.5674 (5) | 0.049 (3) | |
H17 | 0.4323 | 0.3571 | 0.5434 | 0.059* | |
C18 | 0.3278 (12) | 0.5029 (4) | 0.5600 (5) | 0.060 (3) | |
H18A | 0.2615 | 0.5056 | 0.5997 | 0.090* | |
H18B | 0.2926 | 0.5318 | 0.5140 | 0.090* | |
H18C | 0.4370 | 0.5111 | 0.5908 | 0.090* | |
C19 | −0.0940 (12) | 0.5519 (5) | 0.3155 (6) | 0.067 (3) | |
H19A | −0.1539 | 0.5479 | 0.3582 | 0.101* | |
H19B | −0.1529 | 0.5763 | 0.2680 | 0.101* | |
H19C | 0.0072 | 0.5706 | 0.3419 | 0.101* | |
C20 | 0.5091 (11) | 0.3910 (4) | 0.6663 (5) | 0.046 (3) | |
C21 | 0.3696 (12) | 0.3795 (5) | 0.7090 (5) | 0.064 (3) | |
H21A | 0.4125 | 0.3670 | 0.7684 | 0.097* | |
H21B | 0.3010 | 0.3486 | 0.6773 | 0.097* | |
H21C | 0.3092 | 0.4159 | 0.7076 | 0.097* | |
C22 | 0.6418 (12) | 0.3441 (4) | 0.6935 (6) | 0.056 (3) | |
H22 | 0.6460 | 0.3298 | 0.7524 | 0.068* | |
C23 | 0.7955 (12) | 0.3809 (4) | 0.6962 (6) | 0.062 (3) | |
H23A | 0.8727 | 0.3776 | 0.7527 | 0.074* | |
H23B | 0.8449 | 0.3677 | 0.6513 | 0.074* | |
C24 | 0.7321 (12) | 0.4448 (6) | 0.6795 (6) | 0.061 (3) | |
C25 | 0.8370 (12) | 0.4942 (5) | 0.7301 (5) | 0.056 (3) | |
C26 | 1.0021 (12) | 0.4945 (5) | 0.7125 (6) | 0.076 (3) | |
H26A | 1.0697 | 0.5230 | 0.7504 | 0.114* | |
H26B | 0.9916 | 0.5056 | 0.6528 | 0.114* | |
H26C | 1.0486 | 0.4552 | 0.7231 | 0.114* | |
C27 | 0.7601 (14) | 0.5553 (5) | 0.7173 (7) | 0.079 (4) | |
H27A | 0.6515 | 0.5521 | 0.7208 | 0.118* | |
H27B | 0.7614 | 0.5706 | 0.6610 | 0.118* | |
H27C | 0.8183 | 0.5820 | 0.7618 | 0.118* | |
C28 | −0.4053 (12) | 0.4930 (5) | −0.0530 (7) | 0.057 (3) | |
C29 | −0.5343 (13) | 0.5211 (6) | −0.1200 (5) | 0.089 (4) | |
H29A | −0.5178 | 0.5137 | −0.1765 | 0.113* | |
H29B | −0.5344 | 0.5636 | −0.1099 | 0.113* | |
H29C | −0.6352 | 0.5044 | −0.1176 | 0.113* | |
C30 | −0.1479 (11) | 0.2596 (4) | 0.4140 (5) | 0.050 (3) | |
H30A | −0.2411 | 0.2640 | 0.3647 | 0.060* | |
H30B | −0.1058 | 0.2996 | 0.4306 | 0.060* | |
C31 | −0.2030 (10) | 0.2316 (5) | 0.4926 (5) | 0.057 (3) | |
H31A | −0.2857 | 0.2561 | 0.5065 | 0.069* | |
H31B | −0.2442 | 0.1913 | 0.4786 | 0.069* | |
C32 | −0.0500 (11) | 0.2306 (5) | 0.5702 (5) | 0.052 (3) | |
H32 | −0.0084 | 0.2712 | 0.5858 | 0.062* | |
C33 | 0.0751 (12) | 0.1903 (5) | 0.5471 (5) | 0.056 (3) | |
H33A | 0.1705 | 0.1890 | 0.5956 | 0.067* | |
H33B | 0.0335 | 0.1497 | 0.5365 | 0.067* | |
C34 | 0.1180 (13) | 0.2136 (5) | 0.4664 (6) | 0.065 (3) | |
C35 | 0.2708 (12) | 0.2232 (6) | 0.4694 (6) | 0.073 (4) | |
H35 | 0.3462 | 0.2170 | 0.5224 | 0.087* | |
C36 | 0.3303 (11) | 0.2431 (5) | 0.3937 (5) | 0.062 (3) | |
H36A | 0.4226 | 0.2191 | 0.3915 | 0.074* | |
H36B | 0.3645 | 0.2847 | 0.4022 | 0.074* | |
C37 | 0.2024 (11) | 0.2373 (5) | 0.3068 (5) | 0.049 (3) | |
H37 | 0.1902 | 0.1955 | 0.2866 | 0.059* | |
C38 | 0.0422 (11) | 0.2626 (4) | 0.3204 (5) | 0.044 (2) | |
H38 | 0.0649 | 0.3027 | 0.3464 | 0.053* | |
C39 | −0.0217 (11) | 0.2236 (4) | 0.3847 (5) | 0.040 (2) | |
C40 | −0.0880 (11) | 0.2702 (5) | 0.2307 (5) | 0.057 (3) | |
H40A | −0.1233 | 0.2308 | 0.2073 | 0.068* | |
H40B | −0.1799 | 0.2912 | 0.2405 | 0.068* | |
C41 | −0.0238 (11) | 0.3054 (4) | 0.1634 (5) | 0.051 (3) | |
H41A | −0.1062 | 0.3071 | 0.1086 | 0.061* | |
H41B | 0.0000 | 0.3463 | 0.1839 | 0.061* | |
C42 | 0.1269 (11) | 0.2771 (4) | 0.1477 (5) | 0.042 (2) | |
C43 | 0.2515 (10) | 0.2778 (5) | 0.2416 (5) | 0.048 (3) | |
H43 | 0.2577 | 0.3190 | 0.2639 | 0.058* | |
C44 | 0.4132 (11) | 0.2633 (5) | 0.2200 (5) | 0.060 (3) | |
H44A | 0.5036 | 0.2774 | 0.2659 | 0.072* | |
H44B | 0.4247 | 0.2204 | 0.2120 | 0.072* | |
C45 | 0.3995 (11) | 0.2978 (4) | 0.1344 (6) | 0.052 (3) | |
H45 | 0.4735 | 0.3320 | 0.1453 | 0.063* | |
C46 | 0.2231 (9) | 0.3210 (4) | 0.1011 (5) | 0.039 (2) | |
H46 | 0.2187 | 0.3614 | 0.1248 | 0.046* | |
C47 | 0.1024 (11) | 0.2147 (4) | 0.1089 (5) | 0.050 (3) | |
H47A | 0.0446 | 0.1907 | 0.1405 | 0.076* | |
H47B | 0.2045 | 0.1965 | 0.1126 | 0.076* | |
H47C | 0.0424 | 0.2172 | 0.0488 | 0.076* | |
C48 | −0.0847 (13) | 0.1635 (5) | 0.3496 (6) | 0.074 (3) | |
H48A | −0.0176 | 0.1471 | 0.3160 | 0.111* | |
H48B | −0.1918 | 0.1679 | 0.3132 | 0.111* | |
H48C | −0.0852 | 0.1370 | 0.3972 | 0.111* | |
C49 | 0.1748 (10) | 0.3258 (4) | 0.0014 (5) | 0.039 (2) | |
C50 | 0.0006 (11) | 0.3366 (5) | −0.0419 (5) | 0.058 (3) | |
H50A | −0.0181 | 0.3331 | −0.1040 | 0.087* | |
H50B | −0.0286 | 0.3761 | −0.0275 | 0.087* | |
H50C | −0.0629 | 0.3073 | −0.0217 | 0.087* | |
C51 | 0.2858 (13) | 0.3733 (4) | −0.0286 (6) | 0.052 (3) | |
H51 | 0.2345 | 0.3873 | −0.0879 | 0.063* | |
C52 | 0.4308 (12) | 0.3356 (4) | −0.0284 (6) | 0.053 (3) | |
H52A | 0.4560 | 0.3387 | −0.0842 | 0.063* | |
H52B | 0.5227 | 0.3493 | 0.0169 | 0.063* | |
C53 | 0.3917 (11) | 0.2726 (5) | −0.0119 (6) | 0.049 (3) | |
C54 | 0.4524 (11) | 0.2230 (4) | −0.0628 (6) | 0.048 (3) | |
C55 | 0.6336 (10) | 0.2245 (5) | −0.0456 (6) | 0.068 (3) | |
H55A | 0.6660 | 0.1971 | −0.0844 | 0.103* | |
H55B | 0.6821 | 0.2129 | 0.0137 | 0.103* | |
H55C | 0.6672 | 0.2645 | −0.0552 | 0.103* | |
C56 | 0.3923 (13) | 0.1628 (4) | −0.0470 (7) | 0.075 (3) | |
H56A | 0.2774 | 0.1632 | −0.0626 | 0.113* | |
H56B | 0.4321 | 0.1526 | 0.0135 | 0.113* | |
H56C | 0.4286 | 0.1335 | −0.0819 | 0.113* | |
C57 | −0.0183 (14) | 0.2215 (6) | 0.7209 (7) | 0.064 (3) | |
C58 | −0.0760 (12) | 0.1900 (6) | 0.7928 (5) | 0.081 (4) | |
H58A | −0.0585 | 0.1475 | 0.7903 | 0.112* | |
H58B | −0.1881 | 0.1976 | 0.7845 | 0.112* | |
H58C | −0.0175 | 0.2051 | 0.8487 | 0.112* | |
C59 | 0.5086 (16) | 0.1378 (6) | 0.6986 (9) | 0.109 (5) | |
H59A | 0.6156 | 0.1237 | 0.7238 | 0.113* | |
H59B | 0.4769 | 0.1280 | 0.6376 | 0.113* | |
H59C | 0.4369 | 0.1190 | 0.7274 | 0.113* | |
C60 | 0.1277 (17) | 0.5753 (6) | 0.9669 (8) | 0.109 (5) | |
H60A | 0.0398 | 0.5894 | 0.9879 | 0.114* | |
H60B | 0.1243 | 0.5942 | 0.9122 | 0.114* | |
H60C | 0.2268 | 0.5850 | 1.0086 | 0.114* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.050 (4) | 0.082 (5) | 0.034 (4) | 0.002 (4) | 0.011 (3) | −0.006 (4) |
O2 | 0.065 (5) | 0.115 (6) | 0.038 (4) | 0.004 (5) | 0.001 (4) | −0.008 (4) |
O3 | 0.042 (4) | 0.085 (5) | 0.031 (4) | 0.008 (4) | 0.012 (3) | 0.005 (4) |
O4 | 0.042 (4) | 0.078 (5) | 0.033 (3) | −0.005 (4) | 0.016 (3) | −0.006 (3) |
O5 | 0.108 (7) | 0.079 (5) | 0.068 (5) | 0.008 (5) | 0.048 (5) | 0.000 (5) |
O6 | 0.051 (5) | 0.126 (7) | 0.046 (4) | −0.027 (5) | 0.002 (3) | 0.015 (4) |
O7 | 0.043 (4) | 0.091 (5) | 0.021 (3) | −0.004 (4) | 0.011 (3) | 0.002 (3) |
O8 | 0.061 (6) | 0.161 (9) | 0.047 (4) | −0.030 (6) | 0.011 (4) | 0.000 (5) |
O9 | 0.038 (4) | 0.065 (5) | 0.038 (4) | 0.001 (3) | 0.010 (3) | 0.005 (3) |
O10 | 0.037 (4) | 0.057 (4) | 0.034 (3) | −0.004 (3) | 0.009 (3) | 0.000 (3) |
O11 | 0.075 (6) | 0.061 (4) | 0.058 (4) | −0.017 (4) | 0.006 (4) | 0.002 (4) |
O12 | 0.061 (5) | 0.114 (6) | 0.030 (4) | 0.016 (5) | 0.011 (3) | −0.008 (4) |
O13 | 0.099 (7) | 0.098 (6) | 0.084 (5) | −0.013 (6) | 0.050 (6) | −0.008 (5) |
O14 | 0.081 (6) | 0.078 (6) | 0.068 (5) | 0.004 (5) | 0.006 (5) | 0.002 (4) |
C1 | 0.045 (6) | 0.073 (7) | 0.041 (6) | −0.006 (6) | 0.017 (5) | −0.009 (5) |
C2 | 0.035 (6) | 0.086 (8) | 0.044 (6) | −0.025 (6) | 0.017 (5) | −0.017 (6) |
C3 | 0.049 (7) | 0.058 (6) | 0.036 (5) | 0.010 (6) | 0.009 (5) | −0.004 (5) |
C4 | 0.049 (6) | 0.061 (6) | 0.024 (5) | −0.015 (6) | 0.002 (4) | 0.007 (5) |
C5 | 0.056 (7) | 0.046 (6) | 0.046 (6) | 0.001 (6) | 0.017 (5) | −0.011 (5) |
C6 | 0.053 (7) | 0.074 (7) | 0.028 (5) | 0.006 (6) | 0.016 (5) | 0.003 (5) |
C7 | 0.039 (6) | 0.096 (8) | 0.034 (5) | −0.018 (6) | 0.023 (5) | 0.006 (5) |
C8 | 0.027 (5) | 0.059 (6) | 0.038 (5) | −0.005 (5) | 0.008 (4) | −0.006 (5) |
C9 | 0.053 (6) | 0.041 (5) | 0.036 (5) | −0.018 (5) | 0.020 (5) | −0.016 (5) |
C10 | 0.039 (6) | 0.038 (5) | 0.039 (5) | −0.009 (5) | 0.018 (5) | −0.010 (5) |
C11 | 0.051 (7) | 0.086 (8) | 0.037 (5) | −0.008 (6) | 0.023 (5) | −0.001 (6) |
C12 | 0.060 (7) | 0.077 (7) | 0.042 (6) | −0.013 (6) | 0.028 (6) | −0.004 (5) |
C13 | 0.035 (6) | 0.053 (6) | 0.043 (5) | −0.002 (5) | 0.026 (4) | 0.006 (5) |
C14 | 0.040 (6) | 0.074 (7) | 0.035 (5) | 0.002 (6) | 0.024 (5) | −0.003 (5) |
C15 | 0.067 (8) | 0.124 (10) | 0.018 (5) | 0.002 (8) | 0.005 (5) | 0.001 (6) |
C16 | 0.046 (7) | 0.103 (9) | 0.041 (6) | 0.021 (7) | 0.010 (5) | 0.002 (6) |
C17 | 0.057 (7) | 0.059 (6) | 0.040 (6) | 0.003 (6) | 0.029 (5) | 0.004 (5) |
C18 | 0.079 (8) | 0.072 (7) | 0.038 (5) | −0.001 (6) | 0.031 (5) | 0.002 (6) |
C19 | 0.056 (7) | 0.098 (9) | 0.054 (6) | 0.009 (7) | 0.025 (6) | −0.002 (6) |
C20 | 0.045 (6) | 0.052 (6) | 0.038 (6) | 0.005 (6) | 0.006 (5) | −0.003 (5) |
C21 | 0.066 (8) | 0.083 (8) | 0.045 (6) | −0.008 (7) | 0.017 (6) | 0.016 (6) |
C22 | 0.078 (9) | 0.063 (7) | 0.030 (5) | 0.007 (7) | 0.017 (5) | 0.012 (5) |
C23 | 0.056 (7) | 0.067 (7) | 0.065 (7) | 0.034 (7) | 0.020 (6) | 0.027 (6) |
C24 | 0.046 (7) | 0.113 (9) | 0.027 (6) | 0.023 (7) | 0.016 (5) | −0.006 (6) |
C25 | 0.043 (6) | 0.106 (9) | 0.018 (5) | 0.000 (7) | 0.009 (5) | 0.004 (6) |
C26 | 0.060 (8) | 0.107 (9) | 0.069 (7) | −0.007 (7) | 0.032 (6) | −0.008 (7) |
C27 | 0.086 (10) | 0.074 (8) | 0.089 (8) | 0.003 (8) | 0.043 (7) | −0.014 (7) |
C28 | 0.033 (6) | 0.085 (8) | 0.050 (7) | −0.004 (6) | 0.007 (6) | 0.014 (6) |
C29 | 0.077 (9) | 0.152 (12) | 0.028 (6) | 0.004 (9) | −0.002 (6) | 0.016 (7) |
C30 | 0.041 (6) | 0.071 (7) | 0.028 (5) | 0.020 (6) | −0.005 (4) | 0.009 (5) |
C31 | 0.039 (6) | 0.104 (9) | 0.030 (5) | 0.010 (6) | 0.011 (5) | 0.003 (6) |
C32 | 0.056 (7) | 0.073 (7) | 0.029 (5) | 0.006 (6) | 0.015 (5) | 0.005 (5) |
C33 | 0.059 (7) | 0.073 (7) | 0.042 (6) | 0.024 (6) | 0.023 (5) | 0.022 (5) |
C34 | 0.067 (8) | 0.093 (9) | 0.038 (6) | 0.014 (7) | 0.016 (6) | 0.023 (6) |
C35 | 0.035 (7) | 0.155 (12) | 0.032 (5) | 0.022 (7) | 0.014 (5) | 0.037 (7) |
C36 | 0.031 (6) | 0.118 (9) | 0.033 (5) | 0.010 (6) | 0.003 (5) | 0.021 (6) |
C37 | 0.047 (6) | 0.075 (7) | 0.024 (5) | −0.007 (6) | 0.010 (5) | 0.006 (5) |
C38 | 0.046 (6) | 0.056 (6) | 0.025 (5) | 0.006 (5) | 0.000 (4) | −0.001 (5) |
C39 | 0.045 (6) | 0.050 (6) | 0.030 (5) | −0.007 (5) | 0.019 (5) | −0.010 (5) |
C40 | 0.038 (6) | 0.083 (8) | 0.046 (6) | 0.007 (6) | 0.003 (5) | 0.013 (6) |
C41 | 0.051 (7) | 0.071 (7) | 0.026 (5) | 0.003 (6) | 0.000 (5) | 0.005 (5) |
C42 | 0.040 (6) | 0.057 (6) | 0.019 (4) | 0.006 (5) | −0.010 (4) | −0.003 (5) |
C43 | 0.027 (6) | 0.080 (7) | 0.035 (5) | −0.005 (5) | 0.004 (4) | −0.006 (5) |
C44 | 0.048 (7) | 0.111 (9) | 0.013 (4) | −0.004 (7) | −0.003 (4) | 0.020 (5) |
C45 | 0.038 (6) | 0.053 (6) | 0.065 (7) | −0.008 (5) | 0.012 (5) | −0.003 (6) |
C46 | 0.018 (5) | 0.065 (6) | 0.029 (5) | 0.007 (5) | −0.001 (4) | 0.010 (5) |
C47 | 0.050 (7) | 0.044 (6) | 0.053 (6) | 0.001 (5) | 0.006 (5) | −0.004 (5) |
C48 | 0.079 (9) | 0.102 (9) | 0.050 (7) | −0.012 (8) | 0.031 (6) | −0.013 (7) |
C49 | 0.030 (6) | 0.053 (6) | 0.027 (5) | −0.001 (5) | −0.003 (4) | −0.006 (5) |
C50 | 0.050 (7) | 0.085 (7) | 0.039 (5) | 0.024 (6) | 0.009 (5) | 0.020 (6) |
C51 | 0.074 (8) | 0.050 (6) | 0.032 (5) | −0.017 (6) | 0.013 (5) | −0.008 (5) |
C52 | 0.049 (7) | 0.068 (7) | 0.043 (6) | −0.017 (6) | 0.015 (5) | 0.006 (6) |
C53 | 0.031 (6) | 0.068 (7) | 0.037 (6) | 0.002 (6) | −0.011 (5) | −0.005 (5) |
C54 | 0.035 (6) | 0.063 (7) | 0.044 (6) | −0.006 (6) | 0.005 (5) | −0.001 (5) |
C55 | 0.032 (6) | 0.086 (8) | 0.076 (7) | 0.024 (6) | −0.006 (6) | −0.002 (7) |
C56 | 0.069 (8) | 0.067 (8) | 0.101 (9) | −0.012 (7) | 0.042 (7) | −0.015 (7) |
C57 | 0.052 (8) | 0.099 (9) | 0.046 (7) | 0.022 (7) | 0.021 (6) | 0.019 (7) |
C58 | 0.048 (7) | 0.162 (12) | 0.037 (6) | 0.007 (8) | 0.017 (5) | 0.023 (7) |
C59 | 0.097 (11) | 0.094 (10) | 0.152 (13) | −0.019 (9) | 0.061 (10) | 0.004 (10) |
C60 | 0.131 (13) | 0.080 (10) | 0.129 (12) | −0.003 (10) | 0.055 (10) | −0.003 (9) |
Geometric parameters (Å, º) top
O1—C28 | 1.314 (11) | C26—H26A | 0.9600 |
O1—C3 | 1.453 (10) | C26—H26B | 0.9600 |
O2—C28 | 1.246 (12) | C26—H26C | 0.9600 |
O3—C24 | 1.418 (10) | C27—H27A | 0.9600 |
O3—C16 | 1.428 (11) | C27—H27B | 0.9600 |
O4—C24 | 1.407 (11) | C27—H27C | 0.9600 |
O4—C20 | 1.424 (10) | C28—C29 | 1.464 (12) |
O5—C22 | 1.416 (11) | C29—H29A | 0.9600 |
O5—H5 | 0.8200 | C29—H29B | 0.9600 |
O6—C25 | 1.460 (9) | C29—H29C | 0.9600 |
O6—H6 | 0.8200 | C30—C39 | 1.524 (11) |
O7—C57 | 1.344 (12) | C30—C31 | 1.579 (12) |
O7—C32 | 1.481 (10) | C30—H30A | 0.9700 |
O8—C57 | 1.183 (13) | C30—H30B | 0.9700 |
O9—C53 | 1.408 (9) | C31—C32 | 1.553 (11) |
O9—C45 | 1.445 (10) | C31—H31A | 0.9700 |
O10—C53 | 1.411 (10) | C31—H31B | 0.9700 |
O10—C49 | 1.475 (10) | C32—C33 | 1.525 (12) |
O11—C51 | 1.409 (10) | C32—H32 | 0.9800 |
O11—H11 | 0.8200 | C33—C34 | 1.517 (12) |
O12—C54 | 1.461 (10) | C33—H33A | 0.9700 |
O12—H12 | 0.8200 | C33—H33B | 0.9700 |
O13—C59 | 1.388 (14) | C34—C35 | 1.329 (13) |
O13—H13 | 0.8200 | C34—C39 | 1.539 (12) |
O14—C60 | 1.383 (12) | C35—C36 | 1.495 (12) |
O14—H14A | 0.8200 | C35—H35 | 0.9300 |
C1—C10 | 1.527 (12) | C36—C37 | 1.531 (10) |
C1—C2 | 1.565 (11) | C36—H36A | 0.9700 |
C1—H1A | 0.9700 | C36—H36B | 0.9700 |
C1—H1B | 0.9700 | C37—C43 | 1.516 (12) |
C2—C3 | 1.503 (11) | C37—C38 | 1.564 (12) |
C2—H2A | 0.9700 | C37—H37 | 0.9800 |
C2—H2B | 0.9700 | C38—C39 | 1.551 (12) |
C3—C4 | 1.500 (12) | C38—C40 | 1.575 (10) |
C3—H3 | 0.9800 | C38—H38 | 0.9800 |
C4—C5 | 1.507 (11) | C39—C48 | 1.494 (12) |
C4—H4A | 0.9700 | C40—C41 | 1.543 (12) |
C4—H4B | 0.9700 | C40—H40A | 0.9700 |
C5—C6 | 1.317 (12) | C40—H40B | 0.9700 |
C5—C10 | 1.566 (12) | C41—C42 | 1.528 (12) |
C6—C7 | 1.449 (12) | C41—H41A | 0.9700 |
C6—H6A | 0.9300 | C41—H41B | 0.9700 |
C7—C8 | 1.526 (11) | C42—C47 | 1.511 (11) |
C7—H7A | 0.9700 | C42—C46 | 1.589 (12) |
C7—H7B | 0.9700 | C42—C43 | 1.594 (10) |
C8—C14 | 1.486 (11) | C43—C44 | 1.561 (12) |
C8—C9 | 1.582 (12) | C43—H43 | 0.9800 |
C8—H8 | 0.9800 | C44—C45 | 1.539 (11) |
C9—C10 | 1.507 (11) | C44—H44A | 0.9700 |
C9—C11 | 1.564 (11) | C44—H44B | 0.9700 |
C9—H9 | 0.9800 | C45—C46 | 1.566 (11) |
C10—C19 | 1.530 (12) | C45—H45 | 0.9800 |
C11—C12 | 1.537 (12) | C46—C49 | 1.532 (10) |
C11—H11A | 0.9700 | C46—H46 | 0.9800 |
C11—H11B | 0.9700 | C47—H47A | 0.9600 |
C12—C13 | 1.512 (12) | C47—H47B | 0.9600 |
C12—H12A | 0.9700 | C47—H47C | 0.9600 |
C12—H12B | 0.9700 | C48—H48A | 0.9600 |
C13—C18 | 1.542 (12) | C48—H48B | 0.9600 |
C13—C17 | 1.565 (12) | C48—H48C | 0.9600 |
C13—C14 | 1.579 (11) | C49—C50 | 1.503 (11) |
C14—C15 | 1.569 (13) | C49—C51 | 1.585 (12) |
C14—H14 | 0.9800 | C50—H50A | 0.9600 |
C15—C16 | 1.586 (12) | C50—H50B | 0.9600 |
C15—H15A | 0.9700 | C50—H50C | 0.9600 |
C15—H15B | 0.9700 | C51—C52 | 1.510 (13) |
C16—C17 | 1.530 (13) | C51—H51 | 0.9800 |
C16—H16 | 0.9800 | C52—C53 | 1.481 (13) |
C17—C20 | 1.523 (11) | C52—H52A | 0.9700 |
C17—H17 | 0.9800 | C52—H52B | 0.9700 |
C18—H18A | 0.9600 | C53—C54 | 1.540 (13) |
C18—H18B | 0.9600 | C54—C56 | 1.483 (12) |
C18—H18C | 0.9600 | C54—C55 | 1.520 (12) |
C19—H19A | 0.9600 | C55—H55A | 0.9600 |
C19—H19B | 0.9600 | C55—H55B | 0.9600 |
C19—H19C | 0.9600 | C55—H55C | 0.9600 |
C20—C22 | 1.527 (13) | C56—H56A | 0.9600 |
C20—C21 | 1.555 (13) | C56—H56B | 0.9600 |
C21—H21A | 0.9600 | C56—H56C | 0.9600 |
C21—H21B | 0.9600 | C57—C58 | 1.533 (14) |
C21—H21C | 0.9600 | C58—H58A | 0.9600 |
C22—C23 | 1.553 (13) | C58—H58B | 0.9600 |
C22—H22 | 0.9800 | C58—H58C | 0.9600 |
C23—C24 | 1.523 (14) | C59—H59A | 0.9600 |
C23—H23A | 0.9700 | C59—H59B | 0.9600 |
C23—H23B | 0.9700 | C59—H59C | 0.9600 |
C24—C25 | 1.514 (14) | C60—H60A | 0.9600 |
C25—C27 | 1.502 (13) | C60—H60B | 0.9600 |
C25—C26 | 1.527 (13) | C60—H60C | 0.9600 |
| | | |
C28—O1—C3 | 119.0 (8) | C39—C30—C31 | 115.1 (7) |
C24—O3—C16 | 111.5 (8) | C39—C30—H30A | 108.5 |
C24—O4—C20 | 104.2 (7) | C31—C30—H30A | 108.5 |
C22—O5—H5 | 109.5 | C39—C30—H30B | 108.5 |
C25—O6—H6 | 109.5 | C31—C30—H30B | 108.5 |
C57—O7—C32 | 112.3 (7) | H30A—C30—H30B | 107.5 |
C53—O9—C45 | 112.7 (7) | C32—C31—C30 | 105.1 (7) |
C53—O10—C49 | 104.1 (6) | C32—C31—H31A | 110.7 |
C51—O11—H11 | 109.5 | C30—C31—H31A | 110.7 |
C54—O12—H12 | 109.5 | C32—C31—H31B | 110.7 |
C59—O13—H13 | 109.5 | C30—C31—H31B | 110.7 |
C60—O14—H14A | 109.5 | H31A—C31—H31B | 108.8 |
C10—C1—C2 | 114.4 (8) | O7—C32—C33 | 108.6 (7) |
C10—C1—H1A | 108.7 | O7—C32—C31 | 104.2 (7) |
C2—C1—H1A | 108.7 | C33—C32—C31 | 109.2 (7) |
C10—C1—H1B | 108.7 | O7—C32—H32 | 111.5 |
C2—C1—H1B | 108.7 | C33—C32—H32 | 111.5 |
H1A—C1—H1B | 107.6 | C31—C32—H32 | 111.5 |
C3—C2—C1 | 107.2 (8) | C34—C33—C32 | 110.5 (8) |
C3—C2—H2A | 110.3 | C34—C33—H33A | 109.6 |
C1—C2—H2A | 110.3 | C32—C33—H33A | 109.6 |
C3—C2—H2B | 110.3 | C34—C33—H33B | 109.6 |
C1—C2—H2B | 110.3 | C32—C33—H33B | 109.6 |
H2A—C2—H2B | 108.5 | H33A—C33—H33B | 108.1 |
O1—C3—C4 | 108.4 (7) | C35—C34—C33 | 119.3 (9) |
O1—C3—C2 | 106.3 (8) | C35—C34—C39 | 124.1 (8) |
C4—C3—C2 | 111.3 (7) | C33—C34—C39 | 116.7 (9) |
O1—C3—H3 | 110.3 | C34—C35—C36 | 124.8 (9) |
C4—C3—H3 | 110.3 | C34—C35—H35 | 117.6 |
C2—C3—H3 | 110.3 | C36—C35—H35 | 117.6 |
C3—C4—C5 | 113.3 (7) | C35—C36—C37 | 112.3 (8) |
C3—C4—H4A | 108.9 | C35—C36—H36A | 109.1 |
C5—C4—H4A | 108.9 | C37—C36—H36A | 109.1 |
C3—C4—H4B | 108.9 | C35—C36—H36B | 109.1 |
C5—C4—H4B | 108.9 | C37—C36—H36B | 109.2 |
H4A—C4—H4B | 107.7 | H36A—C36—H36B | 107.9 |
C6—C5—C4 | 122.1 (8) | C43—C37—C36 | 107.4 (7) |
C6—C5—C10 | 121.2 (9) | C43—C37—C38 | 107.5 (8) |
C4—C5—C10 | 116.5 (8) | C36—C37—C38 | 107.6 (7) |
C5—C6—C7 | 126.5 (8) | C43—C37—H37 | 111.4 |
C5—C6—H6A | 116.7 | C36—C37—H37 | 111.4 |
C7—C6—H6A | 116.7 | C38—C37—H37 | 111.4 |
C6—C7—C8 | 115.2 (8) | C39—C38—C37 | 111.9 (7) |
C6—C7—H7A | 108.5 | C39—C38—C40 | 111.2 (8) |
C8—C7—H7A | 108.5 | C37—C38—C40 | 111.2 (7) |
C6—C7—H7B | 108.5 | C39—C38—H38 | 107.4 |
C8—C7—H7B | 108.5 | C37—C38—H38 | 107.4 |
H7A—C7—H7B | 107.5 | C40—C38—H38 | 107.4 |
C14—C8—C7 | 111.2 (8) | C48—C39—C30 | 111.4 (8) |
C14—C8—C9 | 108.8 (7) | C48—C39—C34 | 108.3 (8) |
C7—C8—C9 | 106.2 (7) | C30—C39—C34 | 106.6 (7) |
C14—C8—H8 | 110.2 | C48—C39—C38 | 114.5 (7) |
C7—C8—H8 | 110.2 | C30—C39—C38 | 108.4 (7) |
C9—C8—H8 | 110.2 | C34—C39—C38 | 107.4 (7) |
C10—C9—C11 | 113.0 (8) | C41—C40—C38 | 112.3 (8) |
C10—C9—C8 | 114.2 (7) | C41—C40—H40A | 109.2 |
C11—C9—C8 | 109.8 (7) | C38—C40—H40A | 109.2 |
C10—C9—H9 | 106.4 | C41—C40—H40B | 109.2 |
C11—C9—H9 | 106.4 | C38—C40—H40B | 109.2 |
C8—C9—H9 | 106.4 | H40A—C40—H40B | 107.9 |
C9—C10—C1 | 109.8 (7) | C42—C41—C40 | 112.5 (8) |
C9—C10—C19 | 112.6 (7) | C42—C41—H41A | 109.1 |
C1—C10—C19 | 110.3 (8) | C40—C41—H41A | 109.1 |
C9—C10—C5 | 109.0 (7) | C42—C41—H41B | 109.1 |
C1—C10—C5 | 107.9 (7) | C40—C41—H41B | 109.1 |
C19—C10—C5 | 107.0 (7) | H41A—C41—H41B | 107.8 |
C12—C11—C9 | 113.2 (8) | C47—C42—C41 | 114.3 (8) |
C12—C11—H11A | 108.9 | C47—C42—C46 | 114.1 (7) |
C9—C11—H11A | 108.9 | C41—C42—C46 | 113.4 (7) |
C12—C11—H11B | 108.9 | C47—C42—C43 | 112.2 (7) |
C9—C11—H11B | 108.9 | C41—C42—C43 | 103.9 (7) |
H11A—C11—H11B | 107.8 | C46—C42—C43 | 97.0 (7) |
C13—C12—C11 | 114.5 (8) | C37—C43—C44 | 117.2 (8) |
C13—C12—H12A | 108.6 | C37—C43—C42 | 113.0 (7) |
C11—C12—H12A | 108.6 | C44—C43—C42 | 102.6 (6) |
C13—C12—H12B | 108.6 | C37—C43—H43 | 107.9 |
C11—C12—H12B | 108.6 | C44—C43—H43 | 107.8 |
H12A—C12—H12B | 107.6 | C42—C43—H43 | 107.8 |
C12—C13—C18 | 112.2 (8) | C45—C44—C43 | 103.1 (7) |
C12—C13—C17 | 117.1 (7) | C45—C44—H44A | 111.1 |
C18—C13—C17 | 113.2 (8) | C43—C44—H44A | 111.1 |
C12—C13—C14 | 102.9 (7) | C45—C44—H44B | 111.1 |
C18—C13—C14 | 111.6 (7) | C43—C44—H44B | 111.1 |
C17—C13—C14 | 98.3 (7) | H44A—C44—H44B | 109.1 |
C8—C14—C15 | 115.4 (8) | O9—C45—C44 | 105.8 (7) |
C8—C14—C13 | 116.5 (7) | O9—C45—C46 | 114.1 (7) |
C15—C14—C13 | 102.4 (7) | C44—C45—C46 | 107.7 (7) |
C8—C14—H14 | 107.3 | O9—C45—H45 | 109.7 |
C15—C14—H14 | 107.3 | C44—C45—H45 | 109.7 |
C13—C14—H14 | 107.3 | C46—C45—H45 | 109.7 |
C14—C15—C16 | 101.6 (8) | C49—C46—C45 | 110.4 (7) |
C14—C15—H15A | 111.5 | C49—C46—C42 | 119.4 (7) |
C16—C15—H15A | 111.4 | C45—C46—C42 | 102.9 (6) |
C14—C15—H15B | 111.4 | C49—C46—H46 | 107.9 |
C16—C15—H15B | 111.5 | C45—C46—H46 | 107.9 |
H15A—C15—H15B | 109.3 | C42—C46—H46 | 107.9 |
O3—C16—C17 | 114.7 (7) | C42—C47—H47A | 109.5 |
O3—C16—C15 | 104.7 (8) | C42—C47—H47B | 109.5 |
C17—C16—C15 | 107.4 (8) | H47A—C47—H47B | 109.5 |
O3—C16—H16 | 110.0 | C42—C47—H47C | 109.5 |
C17—C16—H16 | 110.0 | H47A—C47—H47C | 109.5 |
C15—C16—H16 | 110.0 | H47B—C47—H47C | 109.5 |
C20—C17—C16 | 110.1 (8) | C39—C48—H48A | 109.5 |
C20—C17—C13 | 121.3 (8) | C39—C48—H48B | 109.5 |
C16—C17—C13 | 104.5 (7) | H48A—C48—H48B | 109.5 |
C20—C17—H17 | 106.7 | C39—C48—H48C | 109.5 |
C16—C17—H17 | 106.7 | H48A—C48—H48C | 109.5 |
C13—C17—H17 | 106.7 | H48B—C48—H48C | 109.5 |
C13—C18—H18A | 109.5 | O10—C49—C50 | 107.3 (7) |
C13—C18—H18B | 109.5 | O10—C49—C46 | 110.7 (7) |
H18A—C18—H18B | 109.5 | C50—C49—C46 | 116.8 (7) |
C13—C18—H18C | 109.5 | O10—C49—C51 | 99.1 (7) |
H18A—C18—H18C | 109.5 | C50—C49—C51 | 111.8 (8) |
H18B—C18—H18C | 109.5 | C46—C49—C51 | 109.6 (7) |
C10—C19—H19A | 109.5 | C49—C50—H50A | 109.5 |
C10—C19—H19B | 109.5 | C49—C50—H50B | 109.5 |
H19A—C19—H19B | 109.5 | H50A—C50—H50B | 109.5 |
C10—C19—H19C | 109.5 | C49—C50—H50C | 109.5 |
H19A—C19—H19C | 109.5 | H50A—C50—H50C | 109.5 |
H19B—C19—H19C | 109.5 | H50B—C50—H50C | 109.5 |
O4—C20—C17 | 109.9 (8) | O11—C51—C52 | 112.1 (8) |
O4—C20—C22 | 101.9 (7) | O11—C51—C49 | 112.6 (7) |
C17—C20—C22 | 110.3 (8) | C52—C51—C49 | 101.4 (7) |
O4—C20—C21 | 106.8 (7) | O11—C51—H51 | 110.2 |
C17—C20—C21 | 114.9 (8) | C52—C51—H51 | 110.2 |
C22—C20—C21 | 112.2 (8) | C49—C51—H51 | 110.2 |
C20—C21—H21A | 109.5 | C53—C52—C51 | 107.3 (8) |
C20—C21—H21B | 109.5 | C53—C52—H52A | 110.3 |
H21A—C21—H21B | 109.5 | C51—C52—H52A | 110.3 |
C20—C21—H21C | 109.5 | C53—C52—H52B | 110.3 |
H21A—C21—H21C | 109.5 | C51—C52—H52B | 110.3 |
H21B—C21—H21C | 109.5 | H52A—C52—H52B | 108.5 |
O5—C22—C20 | 114.9 (8) | O9—C53—O10 | 109.6 (7) |
O5—C22—C23 | 111.3 (9) | O9—C53—C52 | 113.5 (7) |
C20—C22—C23 | 102.9 (8) | O10—C53—C52 | 103.6 (8) |
O5—C22—H22 | 109.2 | O9—C53—C54 | 105.1 (7) |
C20—C22—H22 | 109.2 | O10—C53—C54 | 107.5 (7) |
C23—C22—H22 | 109.2 | C52—C53—C54 | 117.3 (8) |
C24—C23—C22 | 102.7 (8) | O12—C54—C56 | 108.8 (8) |
C24—C23—H23A | 111.2 | O12—C54—C55 | 104.0 (7) |
C22—C23—H23A | 111.2 | C56—C54—C55 | 112.4 (9) |
C24—C23—H23B | 111.2 | O12—C54—C53 | 107.4 (7) |
C22—C23—H23B | 111.2 | C56—C54—C53 | 112.1 (8) |
H23A—C23—H23B | 109.1 | C55—C54—C53 | 111.7 (8) |
O4—C24—O3 | 109.9 (7) | C54—C55—H55A | 109.5 |
O4—C24—C25 | 107.9 (7) | C54—C55—H55B | 109.5 |
O3—C24—C25 | 105.2 (9) | H55A—C55—H55B | 109.5 |
O4—C24—C23 | 104.3 (9) | C54—C55—H55C | 109.5 |
O3—C24—C23 | 112.9 (8) | H55A—C55—H55C | 109.5 |
C25—C24—C23 | 116.5 (8) | H55B—C55—H55C | 109.5 |
O6—C25—C27 | 107.3 (9) | C54—C56—H56A | 109.5 |
O6—C25—C24 | 108.2 (8) | C54—C56—H56B | 109.5 |
C27—C25—C24 | 113.7 (9) | H56A—C56—H56B | 109.5 |
O6—C25—C26 | 103.6 (7) | C54—C56—H56C | 109.5 |
C27—C25—C26 | 112.0 (9) | H56A—C56—H56C | 109.5 |
C24—C25—C26 | 111.5 (9) | H56B—C56—H56C | 109.5 |
C25—C26—H26A | 109.5 | O8—C57—O7 | 125.2 (10) |
C25—C26—H26B | 109.5 | O8—C57—C58 | 124.6 (10) |
H26A—C26—H26B | 109.5 | O7—C57—C58 | 110.1 (10) |
C25—C26—H26C | 109.5 | C57—C58—H58A | 109.5 |
H26A—C26—H26C | 109.5 | C57—C58—H58B | 109.5 |
H26B—C26—H26C | 109.5 | H58A—C58—H58B | 109.5 |
C25—C27—H27A | 109.5 | C57—C58—H58C | 109.5 |
C25—C27—H27B | 109.5 | H58A—C58—H58C | 109.5 |
H27A—C27—H27B | 109.5 | H58B—C58—H58C | 109.5 |
C25—C27—H27C | 109.5 | O13—C59—H59A | 109.5 |
H27A—C27—H27C | 109.5 | O13—C59—H59B | 109.5 |
H27B—C27—H27C | 109.5 | H59A—C59—H59B | 109.5 |
O2—C28—O1 | 120.9 (9) | O13—C59—H59C | 109.5 |
O2—C28—C29 | 124.1 (10) | H59A—C59—H59C | 109.5 |
O1—C28—C29 | 114.5 (10) | H59B—C59—H59C | 109.5 |
C28—C29—H29A | 109.5 | O14—C60—H60A | 109.5 |
C28—C29—H29B | 109.5 | O14—C60—H60B | 109.5 |
H29A—C29—H29B | 109.5 | H60A—C60—H60B | 109.5 |
C28—C29—H29C | 109.5 | O14—C60—H60C | 109.5 |
H29A—C29—H29C | 109.5 | H60A—C60—H60C | 109.5 |
H29B—C29—H29C | 109.5 | H60B—C60—H60C | 109.5 |
| | | |
C10—C1—C2—C3 | 61.6 (10) | C39—C30—C31—C32 | 62.4 (10) |
C28—O1—C3—C4 | 88.5 (10) | C57—O7—C32—C33 | 92.9 (9) |
C28—O1—C3—C2 | −151.8 (8) | C57—O7—C32—C31 | −150.8 (8) |
C1—C2—C3—O1 | −178.3 (7) | C30—C31—C32—O7 | −178.0 (7) |
C1—C2—C3—C4 | −60.5 (10) | C30—C31—C32—C33 | −62.2 (10) |
O1—C3—C4—C5 | 171.8 (7) | O7—C32—C33—C34 | 173.0 (8) |
C2—C3—C4—C5 | 55.2 (11) | C31—C32—C33—C34 | 60.0 (11) |
C3—C4—C5—C6 | 128.5 (10) | C32—C33—C34—C35 | 126.8 (12) |
C3—C4—C5—C10 | −46.8 (11) | C32—C33—C34—C39 | −54.2 (12) |
C4—C5—C6—C7 | 178.2 (9) | C33—C34—C35—C36 | 176.8 (10) |
C10—C5—C6—C7 | −6.7 (16) | C39—C34—C35—C36 | −2 (2) |
C5—C6—C7—C8 | −9.6 (16) | C34—C35—C36—C37 | −13.5 (18) |
C6—C7—C8—C14 | 158.6 (8) | C35—C36—C37—C43 | 160.3 (9) |
C6—C7—C8—C9 | 40.4 (12) | C35—C36—C37—C38 | 44.8 (12) |
C14—C8—C9—C10 | 178.8 (7) | C43—C37—C38—C39 | 178.6 (7) |
C7—C8—C9—C10 | −61.4 (10) | C36—C37—C38—C39 | −65.9 (10) |
C14—C8—C9—C11 | 50.7 (10) | C43—C37—C38—C40 | 53.6 (10) |
C7—C8—C9—C11 | 170.5 (8) | C36—C37—C38—C40 | 169.0 (8) |
C11—C9—C10—C1 | −68.8 (9) | C31—C30—C39—C48 | 64.0 (9) |
C8—C9—C10—C1 | 164.8 (7) | C31—C30—C39—C34 | −53.9 (10) |
C11—C9—C10—C19 | 54.6 (10) | C31—C30—C39—C38 | −169.2 (7) |
C8—C9—C10—C19 | −71.8 (9) | C35—C34—C39—C48 | 108.0 (13) |
C11—C9—C10—C5 | 173.2 (7) | C33—C34—C39—C48 | −70.9 (11) |
C8—C9—C10—C5 | 46.7 (9) | C35—C34—C39—C30 | −132.1 (12) |
C2—C1—C10—C9 | −170.2 (7) | C33—C34—C39—C30 | 49.1 (12) |
C2—C1—C10—C19 | 65.1 (9) | C35—C34—C39—C38 | −16.1 (15) |
C2—C1—C10—C5 | −51.5 (10) | C33—C34—C39—C38 | 165.0 (8) |
C6—C5—C10—C9 | −12.4 (12) | C37—C38—C39—C48 | −70.8 (10) |
C4—C5—C10—C9 | 162.9 (7) | C40—C38—C39—C48 | 54.3 (11) |
C6—C5—C10—C1 | −131.6 (9) | C37—C38—C39—C30 | 164.3 (7) |
C4—C5—C10—C1 | 43.7 (11) | C40—C38—C39—C30 | −70.6 (9) |
C6—C5—C10—C19 | 109.7 (10) | C37—C38—C39—C34 | 49.5 (10) |
C4—C5—C10—C19 | −75.0 (10) | C40—C38—C39—C34 | 174.6 (8) |
C10—C9—C11—C12 | −178.1 (7) | C39—C38—C40—C41 | −176.3 (7) |
C8—C9—C11—C12 | −49.3 (10) | C37—C38—C40—C41 | −50.8 (11) |
C9—C11—C12—C13 | 56.3 (11) | C38—C40—C41—C42 | 55.9 (11) |
C11—C12—C13—C18 | 63.4 (10) | C40—C41—C42—C47 | 63.3 (9) |
C11—C12—C13—C17 | −163.2 (7) | C40—C41—C42—C46 | −163.5 (7) |
C11—C12—C13—C14 | −56.7 (10) | C40—C41—C42—C43 | −59.4 (10) |
C7—C8—C14—C15 | 62.0 (11) | C36—C37—C43—C44 | 61.9 (10) |
C9—C8—C14—C15 | 178.6 (8) | C38—C37—C43—C44 | 177.4 (7) |
C7—C8—C14—C13 | −177.8 (8) | C36—C37—C43—C42 | −179.1 (8) |
C9—C8—C14—C13 | −61.2 (10) | C38—C37—C43—C42 | −63.6 (10) |
C12—C13—C14—C8 | 62.4 (10) | C47—C42—C43—C37 | −58.2 (11) |
C18—C13—C14—C8 | −58.2 (11) | C41—C42—C43—C37 | 65.8 (10) |
C17—C13—C14—C8 | −177.3 (8) | C46—C42—C43—C37 | −177.9 (8) |
C12—C13—C14—C15 | −170.7 (8) | C47—C42—C43—C44 | 68.9 (10) |
C18—C13—C14—C15 | 68.7 (10) | C41—C42—C43—C44 | −167.0 (8) |
C17—C13—C14—C15 | −50.4 (9) | C46—C42—C43—C44 | −50.7 (9) |
C8—C14—C15—C16 | 165.7 (7) | C37—C43—C44—C45 | 162.7 (7) |
C13—C14—C15—C16 | 38.1 (10) | C42—C43—C44—C45 | 38.2 (10) |
C24—O3—C16—C17 | 42.6 (10) | C53—O9—C45—C44 | 160.6 (7) |
C24—O3—C16—C15 | 159.9 (7) | C53—O9—C45—C46 | 42.4 (10) |
C14—C15—C16—O3 | −133.3 (8) | C43—C44—C45—O9 | −132.2 (8) |
C14—C15—C16—C17 | −11.0 (10) | C43—C44—C45—C46 | −9.8 (10) |
O3—C16—C17—C20 | −36.4 (11) | O9—C45—C46—C49 | −33.7 (10) |
C15—C16—C17—C20 | −152.2 (8) | C44—C45—C46—C49 | −150.7 (8) |
O3—C16—C17—C13 | 95.4 (8) | O9—C45—C46—C42 | 94.9 (8) |
C15—C16—C17—C13 | −20.5 (10) | C44—C45—C46—C42 | −22.2 (9) |
C12—C13—C17—C20 | −82.9 (11) | C47—C42—C46—C49 | 48.1 (10) |
C18—C13—C17—C20 | 50.1 (11) | C41—C42—C46—C49 | −85.2 (10) |
C14—C13—C17—C20 | 168.0 (8) | C43—C42—C46—C49 | 166.3 (8) |
C12—C13—C17—C16 | 152.2 (8) | C47—C42—C46—C45 | −74.5 (8) |
C18—C13—C17—C16 | −74.8 (9) | C41—C42—C46—C45 | 152.1 (7) |
C14—C13—C17—C16 | 43.1 (9) | C43—C42—C46—C45 | 43.7 (8) |
C24—O4—C20—C17 | −67.8 (9) | C53—O10—C49—C50 | 165.5 (7) |
C24—O4—C20—C22 | 49.2 (8) | C53—O10—C49—C46 | −66.0 (8) |
C24—O4—C20—C21 | 167.0 (7) | C53—O10—C49—C51 | 49.2 (7) |
C16—C17—C20—O4 | 49.4 (10) | C45—C46—C49—O10 | 46.0 (9) |
C13—C17—C20—O4 | −72.9 (10) | C42—C46—C49—O10 | −73.0 (9) |
C16—C17—C20—C22 | −62.2 (11) | C45—C46—C49—C50 | 169.2 (8) |
C13—C17—C20—C22 | 175.5 (8) | C42—C46—C49—C50 | 50.3 (12) |
C16—C17—C20—C21 | 169.8 (9) | C45—C46—C49—C51 | −62.4 (10) |
C13—C17—C20—C21 | 47.6 (12) | C42—C46—C49—C51 | 178.7 (7) |
O4—C20—C22—O5 | −153.3 (7) | O10—C49—C51—O11 | −152.6 (7) |
C17—C20—C22—O5 | −36.6 (11) | C50—C49—C51—O11 | 94.5 (9) |
C21—C20—C22—O5 | 92.8 (10) | C46—C49—C51—O11 | −36.6 (10) |
O4—C20—C22—C23 | −32.1 (8) | O10—C49—C51—C52 | −32.6 (7) |
C17—C20—C22—C23 | 84.5 (9) | C50—C49—C51—C52 | −145.5 (7) |
C21—C20—C22—C23 | −146.0 (8) | C46—C49—C51—C52 | 83.3 (9) |
O5—C22—C23—C24 | 129.2 (8) | O11—C51—C52—C53 | 127.3 (8) |
C20—C22—C23—C24 | 5.6 (9) | C49—C51—C52—C53 | 7.0 (9) |
C20—O4—C24—O3 | 75.3 (9) | C45—O9—C53—O10 | −65.0 (9) |
C20—O4—C24—C25 | −170.5 (7) | C45—O9—C53—C52 | 50.3 (10) |
C20—O4—C24—C23 | −46.0 (8) | C45—O9—C53—C54 | 179.8 (7) |
C16—O3—C24—O4 | −62.7 (10) | C49—O10—C53—O9 | 75.5 (8) |
C16—O3—C24—C25 | −178.6 (7) | C49—O10—C53—C52 | −46.0 (8) |
C16—O3—C24—C23 | 53.3 (10) | C49—O10—C53—C54 | −170.8 (7) |
C22—C23—C24—O4 | 23.3 (9) | C51—C52—C53—O9 | −96.0 (9) |
C22—C23—C24—O3 | −96.0 (9) | C51—C52—C53—O10 | 22.8 (9) |
C22—C23—C24—C25 | 142.1 (8) | C51—C52—C53—C54 | 141.1 (8) |
O4—C24—C25—O6 | 61.8 (10) | O9—C53—C54—O12 | 177.8 (7) |
O3—C24—C25—O6 | 179.1 (7) | O10—C53—C54—O12 | 61.1 (9) |
C23—C24—C25—O6 | −55.1 (11) | C52—C53—C54—O12 | −55.0 (10) |
O4—C24—C25—C27 | −57.3 (10) | O9—C53—C54—C56 | 58.4 (10) |
O3—C24—C25—C27 | 60.0 (10) | O10—C53—C54—C56 | −58.3 (10) |
C23—C24—C25—C27 | −174.1 (8) | C52—C53—C54—C56 | −174.4 (9) |
O4—C24—C25—C26 | 175.1 (8) | O9—C53—C54—C55 | −68.7 (10) |
O3—C24—C25—C26 | −67.7 (10) | O10—C53—C54—C55 | 174.6 (8) |
C23—C24—C25—C26 | 58.2 (11) | C52—C53—C54—C55 | 58.4 (11) |
C3—O1—C28—O2 | 5.0 (14) | C32—O7—C57—O8 | −2.9 (15) |
C3—O1—C28—C29 | 177.3 (9) | C32—O7—C57—C58 | −179.0 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O13 | 0.82 | 1.92 | 2.742 (11) | 178 |
O6—H6···O2i | 0.82 | 2.25 | 2.752 (10) | 120 |
O12—H12···O8ii | 0.82 | 2.42 | 2.780 (10) | 108 |
O11—H11···O14ii | 0.82 | 2.00 | 2.755 (10) | 153 |
O12—H12···O10 | 0.82 | 2.47 | 2.776 (8) | 104 |
O13—H13···O12iii | 0.82 | 2.19 | 2.708 (9) | 121 |
O14—H14A···O6iv | 0.82 | 2.03 | 2.673 (9) | 135 |
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z−1; (iii) x, y, z+1; (iv) x−1, y, z. |