The eplerenone molecule of the title compound, C
24H
30O
6·C
4H
8O, contains three six-membered rings, two five-membered rings and one three-membered ring. In the crystal structure, the eplerenone molecules are linked
via C—H

O hydrogen bonds, forming a 303 Å
3 cavity, which is occupied by two disordered solvent THF molecules.
Supporting information
CCDC reference: 647472
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.007 Å
- H-atom completeness 79%
- Disorder in solvent or counterion
- R factor = 0.070
- wR factor = 0.229
- Data-to-parameter ratio = 10.7
checkCIF/PLATON results
No syntax errors found
Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
calculated from the _atom_site* data lies outside
the range 0.99 <> 1.01
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_weight 486.58
TEST: Calculate formula weight from _atom_site_*
atom mass num sum
C 12.01 28.00 336.31
H 1.01 30.00 30.24
O 16.00 7.00 111.99
Calculated formula weight 478.54
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................ 486.58
PLAT044_ALERT_1_C Calculated and Reported Dx Differ .............. ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 5
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O8
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O7
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C81
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C84
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C71
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C74
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C28 H38 O7
Atom count from the _atom_site data: C28 H30 O7
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C28 H38 O7
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 112.00 112.00 0.00
H 152.00 120.00 32.00
O 28.00 28.00 0.00
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 27.40
From the CIF: _reflns_number_total 3304
Count of symmetry unique reflns 3304
Completeness (_total/calc) 100.00%
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 C4 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
12 ALERT level G = General alerts; check
15 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
8 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
9
α,11-Epoxy-7
α-(methoxycarbonyl)-3-oxo-17
α-pregn-4-ene-21,17-carbolactone
top
Crystal data top
C24H30O6·C4H8O | F(000) = 1048 |
Mr = 486.58 | Dx = 1.262 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3608 reflections |
a = 8.2974 (7) Å | θ = 3.0–24.0° |
b = 13.1968 (11) Å | µ = 0.09 mm−1 |
c = 23.3855 (15) Å | T = 295 K |
V = 2560.7 (3) Å3 | Block, colorless |
Z = 4 | 0.32 × 0.19 × 0.13 mm |
Data collection top
Rigaku RAXIS-RAPID IP diffractometer | 2006 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.053 |
Graphite monochromator | θmax = 27.4°, θmin = 3.0° |
Detector resolution: 10.0 pixels mm-1 | h = −10→9 |
ω scans | k = −17→17 |
24665 measured reflections | l = −30→30 |
3304 independent reflections | |
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)] = 0.070 | H-atom parameters constrained |
wR(F2) = 0.229 | w = 1/[σ2(Fo2) + (0.1455P)2 + 0.1324P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3304 reflections | Δρmax = 0.31 e Å−3 |
308 parameters | Δρmin = −0.35 e Å−3 |
10 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.045 (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 | Occ. (<1) |
O1 | −0.0777 (6) | 0.5597 (4) | 0.10371 (19) | 0.1062 (15) | |
O2 | 0.1430 (3) | 0.8187 (2) | 0.29267 (12) | 0.0515 (7) | |
O3 | 0.4864 (4) | 0.8351 (2) | 0.49774 (12) | 0.0638 (9) | |
O4 | 0.3796 (5) | 0.8940 (3) | 0.57841 (14) | 0.0808 (11) | |
O5 | 0.4781 (5) | 0.9194 (3) | 0.22682 (17) | 0.0838 (12) | |
O6 | 0.3069 (4) | 0.8341 (3) | 0.17287 (14) | 0.0698 (9) | |
C1 | −0.0151 (6) | 0.5823 (4) | 0.1502 (3) | 0.0714 (13) | |
C2 | 0.1545 (6) | 0.6066 (4) | 0.1537 (2) | 0.0660 (12) | |
H2 | 0.2137 | 0.6067 | 0.1199 | 0.079* | |
C3 | 0.2317 (5) | 0.6290 (3) | 0.2021 (2) | 0.0565 (11) | |
C4 | 0.1439 (5) | 0.6361 (3) | 0.25949 (19) | 0.0517 (10) | |
C5 | −0.0377 (5) | 0.6549 (4) | 0.2481 (2) | 0.0671 (13) | |
H5A | −0.0964 | 0.6481 | 0.2838 | 0.081* | |
H5B | −0.0520 | 0.7239 | 0.2346 | 0.081* | |
C6 | −0.1086 (6) | 0.5822 (4) | 0.2044 (3) | 0.0743 (14) | |
H6A | −0.1095 | 0.5143 | 0.2202 | 0.089* | |
H6B | −0.2191 | 0.6015 | 0.1964 | 0.089* | |
C7 | 0.4105 (5) | 0.6463 (4) | 0.20123 (19) | 0.0552 (10) | |
H7A | 0.4448 | 0.6561 | 0.1620 | 0.066* | |
H7B | 0.4640 | 0.5861 | 0.2156 | 0.066* | |
C8 | 0.4650 (5) | 0.7382 (3) | 0.23689 (18) | 0.0516 (10) | |
H8 | 0.5829 | 0.7359 | 0.2390 | 0.062* | |
C9 | 0.3999 (4) | 0.7247 (3) | 0.29851 (17) | 0.0480 (9) | |
H9 | 0.4371 | 0.6582 | 0.3117 | 0.058* | |
C10 | 0.2174 (5) | 0.7203 (3) | 0.29697 (19) | 0.0480 (9) | |
C11 | 0.1274 (5) | 0.7624 (3) | 0.34578 (18) | 0.0526 (10) | |
H11 | 0.0212 | 0.7320 | 0.3523 | 0.063* | |
C12 | 0.2053 (5) | 0.8070 (4) | 0.39790 (19) | 0.0565 (11) | |
H12A | 0.1537 | 0.7794 | 0.4317 | 0.068* | |
H12B | 0.1878 | 0.8797 | 0.3979 | 0.068* | |
C13 | 0.3866 (5) | 0.7861 (3) | 0.40120 (17) | 0.0506 (10) | |
C14 | 0.4611 (5) | 0.8016 (3) | 0.34114 (18) | 0.0525 (10) | |
H14 | 0.4285 | 0.8688 | 0.3276 | 0.063* | |
C15 | 0.6446 (5) | 0.8043 (5) | 0.3516 (2) | 0.0675 (13) | |
H15A | 0.6968 | 0.8508 | 0.3254 | 0.081* | |
H15B | 0.6914 | 0.7375 | 0.3468 | 0.081* | |
C16 | 0.6632 (6) | 0.8413 (5) | 0.4143 (2) | 0.0690 (13) | |
H16A | 0.7161 | 0.7901 | 0.4374 | 0.083* | |
H16B | 0.7262 | 0.9031 | 0.4158 | 0.083* | |
C17 | 0.4921 (6) | 0.8602 (3) | 0.43579 (18) | 0.0555 (10) | |
C18 | 0.4397 (6) | 0.9725 (3) | 0.4349 (2) | 0.0603 (11) | |
H18A | 0.5329 | 1.0169 | 0.4346 | 0.072* | |
H18B | 0.3741 | 0.9868 | 0.4015 | 0.072* | |
C19 | 0.3443 (7) | 0.9860 (4) | 0.4886 (2) | 0.0665 (12) | |
H19A | 0.3635 | 1.0523 | 0.5050 | 0.080* | |
H19B | 0.2300 | 0.9785 | 0.4811 | 0.080* | |
C20 | 0.4026 (6) | 0.9045 (4) | 0.52768 (19) | 0.0616 (11) | |
C21 | 0.1664 (6) | 0.5344 (4) | 0.2914 (2) | 0.0666 (12) | |
H21A | 0.2780 | 0.5257 | 0.3010 | 0.100* | |
H21B | 0.1322 | 0.4796 | 0.2672 | 0.100* | |
H21C | 0.1030 | 0.5346 | 0.3257 | 0.100* | |
C22 | 0.4124 (7) | 0.6769 (4) | 0.4232 (2) | 0.0670 (12) | |
H22A | 0.3882 | 0.6741 | 0.4634 | 0.101* | |
H22B | 0.5225 | 0.6573 | 0.4171 | 0.101* | |
H22C | 0.3425 | 0.6315 | 0.4029 | 0.101* | |
C23 | 0.4194 (5) | 0.8405 (4) | 0.21240 (18) | 0.0554 (10) | |
C24 | 0.2483 (9) | 0.9285 (4) | 0.1484 (3) | 0.0949 (19) | |
H24A | 0.2075 | 0.9711 | 0.1784 | 0.142* | |
H24B | 0.1636 | 0.9142 | 0.1216 | 0.142* | |
H24C | 0.3350 | 0.9624 | 0.1291 | 0.142* | |
O7 | 0.302 (3) | 0.4143 (19) | 0.4767 (10) | 0.243 (7)* | 0.479 (9) |
C71 | 0.159 (3) | 0.357 (2) | 0.4816 (9) | 0.159 (3)* | 0.479 (9) |
C72 | 0.152 (3) | 0.3217 (19) | 0.4185 (9) | 0.159 (3)* | 0.479 (9) |
C73 | 0.317 (3) | 0.2670 (15) | 0.4240 (11) | 0.159 (3)* | 0.479 (9) |
C74 | 0.383 (3) | 0.3772 (15) | 0.4286 (11) | 0.159 (3)* | 0.479 (9) |
O8 | 0.306 (3) | 0.2823 (18) | 0.4922 (11) | 0.243 (7)* | 0.521 (9) |
C81 | 0.192 (3) | 0.3585 (19) | 0.4992 (9) | 0.159 (3)* | 0.521 (9) |
C82 | 0.184 (3) | 0.4072 (17) | 0.4393 (8) | 0.159 (3)* | 0.521 (9) |
C83 | 0.282 (3) | 0.3332 (18) | 0.4006 (9) | 0.159 (3)* | 0.521 (9) |
C84 | 0.400 (3) | 0.2800 (19) | 0.4427 (9) | 0.159 (3)* | 0.521 (9) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.101 (3) | 0.134 (4) | 0.083 (3) | −0.046 (3) | −0.030 (2) | −0.009 (3) |
O2 | 0.0516 (14) | 0.0467 (15) | 0.0562 (16) | 0.0044 (13) | −0.0006 (13) | 0.0044 (12) |
O3 | 0.082 (2) | 0.0636 (19) | 0.0458 (16) | 0.0165 (17) | −0.0072 (15) | 0.0007 (14) |
O4 | 0.111 (3) | 0.082 (2) | 0.0495 (19) | 0.009 (2) | 0.0006 (19) | −0.0004 (17) |
O5 | 0.106 (3) | 0.070 (2) | 0.075 (2) | −0.031 (2) | −0.004 (2) | 0.0016 (18) |
O6 | 0.076 (2) | 0.066 (2) | 0.068 (2) | 0.0022 (18) | −0.0139 (17) | 0.0087 (16) |
C1 | 0.073 (3) | 0.065 (3) | 0.077 (3) | −0.012 (3) | −0.011 (3) | −0.005 (3) |
C2 | 0.069 (3) | 0.070 (3) | 0.059 (3) | −0.007 (2) | 0.001 (2) | −0.012 (2) |
C3 | 0.057 (2) | 0.049 (2) | 0.064 (3) | 0.0000 (19) | 0.001 (2) | −0.007 (2) |
C4 | 0.047 (2) | 0.049 (2) | 0.059 (2) | 0.0035 (18) | 0.0026 (19) | −0.0043 (18) |
C5 | 0.048 (2) | 0.067 (3) | 0.086 (3) | 0.000 (2) | −0.004 (2) | −0.017 (3) |
C6 | 0.059 (3) | 0.067 (3) | 0.097 (4) | −0.005 (2) | −0.010 (3) | −0.018 (3) |
C7 | 0.051 (2) | 0.061 (2) | 0.054 (2) | 0.003 (2) | 0.0061 (19) | −0.009 (2) |
C8 | 0.0413 (19) | 0.063 (3) | 0.051 (2) | −0.0042 (19) | 0.0034 (18) | −0.0002 (19) |
C9 | 0.0414 (18) | 0.051 (2) | 0.051 (2) | 0.0025 (17) | 0.0025 (18) | 0.0019 (18) |
C10 | 0.0464 (19) | 0.044 (2) | 0.054 (2) | 0.0049 (17) | 0.0066 (18) | 0.0015 (17) |
C11 | 0.052 (2) | 0.055 (2) | 0.052 (2) | 0.0022 (19) | 0.0089 (19) | 0.0019 (19) |
C12 | 0.053 (2) | 0.066 (3) | 0.050 (2) | 0.002 (2) | 0.005 (2) | −0.001 (2) |
C13 | 0.053 (2) | 0.054 (2) | 0.045 (2) | 0.0040 (18) | 0.0001 (18) | 0.0028 (18) |
C14 | 0.049 (2) | 0.059 (2) | 0.049 (2) | 0.0012 (19) | 0.0031 (18) | 0.0004 (19) |
C15 | 0.048 (2) | 0.097 (4) | 0.057 (3) | −0.004 (3) | −0.002 (2) | −0.009 (3) |
C16 | 0.056 (2) | 0.087 (4) | 0.065 (3) | 0.003 (3) | −0.006 (2) | −0.009 (3) |
C17 | 0.063 (2) | 0.058 (2) | 0.045 (2) | 0.005 (2) | −0.0079 (19) | 0.0006 (19) |
C18 | 0.067 (3) | 0.054 (2) | 0.059 (3) | −0.001 (2) | −0.005 (2) | 0.010 (2) |
C19 | 0.084 (3) | 0.057 (3) | 0.059 (3) | 0.015 (3) | −0.006 (2) | −0.003 (2) |
C20 | 0.071 (3) | 0.063 (3) | 0.050 (2) | 0.005 (2) | −0.001 (2) | −0.001 (2) |
C21 | 0.068 (3) | 0.055 (3) | 0.077 (3) | −0.004 (2) | 0.006 (3) | 0.004 (2) |
C22 | 0.081 (3) | 0.061 (3) | 0.058 (3) | 0.013 (3) | 0.004 (2) | 0.008 (2) |
C23 | 0.057 (2) | 0.061 (3) | 0.048 (2) | −0.008 (2) | 0.0103 (19) | 0.0015 (19) |
C24 | 0.114 (5) | 0.073 (4) | 0.098 (4) | 0.021 (4) | −0.014 (4) | 0.018 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.241 (7) | C13—C17 | 1.541 (6) |
O2—C10 | 1.441 (5) | C13—C22 | 1.545 (6) |
O2—C11 | 1.453 (5) | C13—C14 | 1.548 (6) |
O3—C20 | 1.346 (5) | C14—C15 | 1.543 (6) |
O3—C17 | 1.487 (5) | C14—H14 | 0.9800 |
O4—C20 | 1.209 (6) | C15—C16 | 1.553 (7) |
O5—C23 | 1.198 (6) | C15—H15A | 0.9700 |
O6—C23 | 1.316 (6) | C15—H15B | 0.9700 |
O6—C24 | 1.454 (6) | C16—C17 | 1.526 (7) |
C1—C2 | 1.445 (7) | C16—H16A | 0.9700 |
C1—C6 | 1.485 (8) | C16—H16B | 0.9700 |
C2—C3 | 1.335 (7) | C17—C18 | 1.545 (7) |
C2—H2 | 0.9300 | C18—C19 | 1.495 (7) |
C3—C7 | 1.502 (6) | C18—H18A | 0.9700 |
C3—C4 | 1.529 (6) | C18—H18B | 0.9700 |
C4—C10 | 1.541 (6) | C19—C20 | 1.492 (7) |
C4—C21 | 1.546 (6) | C19—H19A | 0.9700 |
C4—C5 | 1.551 (6) | C19—H19B | 0.9700 |
C5—C6 | 1.521 (7) | C21—H21A | 0.9600 |
C5—H5A | 0.9700 | C21—H21B | 0.9600 |
C5—H5B | 0.9700 | C21—H21C | 0.9600 |
C6—H6A | 0.9700 | C22—H22A | 0.9600 |
C6—H6B | 0.9700 | C22—H22B | 0.9600 |
C7—C8 | 1.539 (6) | C22—H22C | 0.9600 |
C7—H7A | 0.9700 | C24—H24A | 0.9600 |
C7—H7B | 0.9700 | C24—H24B | 0.9600 |
C8—C23 | 1.514 (6) | C24—H24C | 0.9600 |
C8—C9 | 1.549 (6) | O7—C74 | 1.399 (10) |
C8—H8 | 0.9800 | O7—C71 | 1.409 (10) |
C9—C14 | 1.510 (6) | C71—C72 | 1.547 (10) |
C9—C10 | 1.516 (5) | C72—C73 | 1.550 (10) |
C9—H9 | 0.9800 | C73—C74 | 1.556 (10) |
C10—C11 | 1.473 (6) | O8—C81 | 1.389 (10) |
C11—C12 | 1.500 (6) | O8—C84 | 1.398 (10) |
C11—H11 | 0.9800 | C81—C82 | 1.542 (10) |
C12—C13 | 1.532 (6) | C82—C83 | 1.559 (10) |
C12—H12A | 0.9700 | C83—C84 | 1.555 (10) |
C12—H12B | 0.9700 | | |
| | | |
C10—O2—C11 | 61.2 (3) | C22—C13—C14 | 111.7 (4) |
C20—O3—C17 | 111.8 (3) | C9—C14—C15 | 116.9 (4) |
C23—O6—C24 | 117.3 (4) | C9—C14—C13 | 112.1 (3) |
O1—C1—C2 | 120.6 (6) | C15—C14—C13 | 104.6 (4) |
O1—C1—C6 | 121.9 (5) | C9—C14—H14 | 107.6 |
C2—C1—C6 | 117.4 (5) | C15—C14—H14 | 107.6 |
C3—C2—C1 | 124.3 (5) | C13—C14—H14 | 107.6 |
C3—C2—H2 | 117.8 | C14—C15—C16 | 104.8 (4) |
C1—C2—H2 | 117.8 | C14—C15—H15A | 110.8 |
C2—C3—C7 | 119.8 (4) | C16—C15—H15A | 110.8 |
C2—C3—C4 | 122.0 (4) | C14—C15—H15B | 110.8 |
C7—C3—C4 | 118.2 (4) | C16—C15—H15B | 110.8 |
C3—C4—C10 | 110.8 (3) | H15A—C15—H15B | 108.9 |
C3—C4—C21 | 108.2 (4) | C17—C16—C15 | 105.7 (3) |
C10—C4—C21 | 107.7 (4) | C17—C16—H16A | 110.6 |
C3—C4—C5 | 108.8 (4) | C15—C16—H16A | 110.6 |
C10—C4—C5 | 111.5 (3) | C17—C16—H16B | 110.6 |
C21—C4—C5 | 109.8 (4) | C15—C16—H16B | 110.6 |
C6—C5—C4 | 112.9 (4) | H16A—C16—H16B | 108.7 |
C6—C5—H5A | 109.0 | O3—C17—C16 | 108.3 (4) |
C4—C5—H5A | 109.0 | O3—C17—C13 | 110.6 (4) |
C6—C5—H5B | 109.0 | C16—C17—C13 | 104.6 (4) |
C4—C5—H5B | 109.0 | O3—C17—C18 | 102.6 (3) |
H5A—C5—H5B | 107.8 | C16—C17—C18 | 114.5 (4) |
C1—C6—C5 | 111.8 (4) | C13—C17—C18 | 116.2 (4) |
C1—C6—H6A | 109.3 | C19—C18—C17 | 104.5 (4) |
C5—C6—H6A | 109.3 | C19—C18—H18A | 110.8 |
C1—C6—H6B | 109.3 | C17—C18—H18A | 110.8 |
C5—C6—H6B | 109.3 | C19—C18—H18B | 110.8 |
H6A—C6—H6B | 107.9 | C17—C18—H18B | 110.8 |
C3—C7—C8 | 113.7 (4) | H18A—C18—H18B | 108.9 |
C3—C7—H7A | 108.8 | C20—C19—C18 | 104.9 (4) |
C8—C7—H7A | 108.8 | C20—C19—H19A | 110.8 |
C3—C7—H7B | 108.8 | C18—C19—H19A | 110.8 |
C8—C7—H7B | 108.8 | C20—C19—H19B | 110.8 |
H7A—C7—H7B | 107.7 | C18—C19—H19B | 110.8 |
C23—C8—C7 | 115.1 (4) | H19A—C19—H19B | 108.8 |
C23—C8—C9 | 111.5 (3) | O4—C20—O3 | 120.9 (5) |
C7—C8—C9 | 108.1 (3) | O4—C20—C19 | 129.3 (5) |
C23—C8—H8 | 107.2 | O3—C20—C19 | 109.8 (4) |
C7—C8—H8 | 107.2 | C4—C21—H21A | 109.5 |
C9—C8—H8 | 107.2 | C4—C21—H21B | 109.5 |
C14—C9—C10 | 112.2 (3) | H21A—C21—H21B | 109.5 |
C14—C9—C8 | 114.8 (3) | C4—C21—H21C | 109.5 |
C10—C9—C8 | 109.3 (3) | H21A—C21—H21C | 109.5 |
C14—C9—H9 | 106.7 | H21B—C21—H21C | 109.5 |
C10—C9—H9 | 106.7 | C13—C22—H22A | 109.5 |
C8—C9—H9 | 106.7 | C13—C22—H22B | 109.5 |
O2—C10—C11 | 59.8 (3) | H22A—C22—H22B | 109.5 |
O2—C10—C9 | 113.3 (3) | C13—C22—H22C | 109.5 |
C11—C10—C9 | 118.3 (4) | H22A—C22—H22C | 109.5 |
O2—C10—C4 | 116.1 (3) | H22B—C22—H22C | 109.5 |
C11—C10—C4 | 120.8 (3) | O5—C23—O6 | 122.8 (5) |
C9—C10—C4 | 115.9 (3) | O5—C23—C8 | 124.5 (4) |
O2—C11—C10 | 59.0 (2) | O6—C23—C8 | 112.7 (4) |
O2—C11—C12 | 117.1 (4) | O6—C24—H24A | 109.5 |
C10—C11—C12 | 124.0 (4) | O6—C24—H24B | 109.5 |
O2—C11—H11 | 115.0 | H24A—C24—H24B | 109.5 |
C10—C11—H11 | 115.0 | O6—C24—H24C | 109.5 |
C12—C11—H11 | 115.0 | H24A—C24—H24C | 109.5 |
C11—C12—C13 | 113.2 (4) | H24B—C24—H24C | 109.5 |
C11—C12—H12A | 108.9 | C74—O7—C71 | 106 (2) |
C13—C12—H12A | 108.9 | O7—C71—C72 | 97 (2) |
C11—C12—H12B | 108.9 | C71—C72—C73 | 91.6 (18) |
C13—C12—H12B | 108.9 | C72—C73—C74 | 83.0 (18) |
H12A—C12—H12B | 107.8 | O7—C74—C73 | 102 (2) |
C12—C13—C17 | 118.0 (4) | C81—O8—C84 | 120 (2) |
C12—C13—C22 | 108.7 (4) | O8—C81—C82 | 103 (2) |
C17—C13—C22 | 109.8 (4) | C81—C82—C83 | 104.1 (17) |
C12—C13—C14 | 108.8 (3) | C84—C83—C82 | 104.2 (16) |
C17—C13—C14 | 99.6 (3) | O8—C84—C83 | 99.3 (18) |
| | | |
O1—C1—C2—C3 | −178.2 (5) | C10—C9—C14—C15 | 173.2 (4) |
C6—C1—C2—C3 | −0.1 (8) | C8—C9—C14—C15 | −61.3 (5) |
C1—C2—C3—C7 | 175.9 (5) | C10—C9—C14—C13 | 52.3 (5) |
C1—C2—C3—C4 | −3.1 (8) | C8—C9—C14—C13 | 177.9 (3) |
C2—C3—C4—C10 | −144.3 (5) | C12—C13—C14—C9 | −65.5 (5) |
C7—C3—C4—C10 | 36.7 (5) | C17—C13—C14—C9 | 170.4 (3) |
C2—C3—C4—C21 | 97.8 (5) | C22—C13—C14—C9 | 54.5 (5) |
C7—C3—C4—C21 | −81.2 (5) | C12—C13—C14—C15 | 166.9 (4) |
C2—C3—C4—C5 | −21.4 (6) | C17—C13—C14—C15 | 42.7 (5) |
C7—C3—C4—C5 | 159.5 (4) | C22—C13—C14—C15 | −73.1 (5) |
C3—C4—C5—C6 | 49.1 (6) | C9—C14—C15—C16 | −150.7 (4) |
C10—C4—C5—C6 | 171.6 (4) | C13—C14—C15—C16 | −26.0 (5) |
C21—C4—C5—C6 | −69.1 (6) | C14—C15—C16—C17 | −1.4 (6) |
O1—C1—C6—C5 | −153.6 (5) | C20—O3—C17—C16 | 137.2 (4) |
C2—C1—C6—C5 | 28.3 (7) | C20—O3—C17—C13 | −108.8 (4) |
C4—C5—C6—C1 | −53.7 (7) | C20—O3—C17—C18 | 15.8 (5) |
C2—C3—C7—C8 | 136.3 (5) | C15—C16—C17—O3 | 146.5 (4) |
C4—C3—C7—C8 | −44.6 (6) | C15—C16—C17—C13 | 28.5 (5) |
C3—C7—C8—C23 | −70.5 (5) | C15—C16—C17—C18 | −99.7 (5) |
C3—C7—C8—C9 | 54.9 (5) | C12—C13—C17—O3 | 82.5 (5) |
C23—C8—C9—C14 | −60.2 (4) | C22—C13—C17—O3 | −42.7 (5) |
C7—C8—C9—C14 | 172.3 (3) | C14—C13—C17—O3 | −160.1 (3) |
C23—C8—C9—C10 | 66.8 (4) | C12—C13—C17—C16 | −161.1 (4) |
C7—C8—C9—C10 | −60.7 (4) | C22—C13—C17—C16 | 73.7 (4) |
C11—O2—C10—C9 | −110.3 (4) | C14—C13—C17—C16 | −43.7 (4) |
C11—O2—C10—C4 | 112.0 (4) | C12—C13—C17—C18 | −33.9 (6) |
C14—C9—C10—O2 | 48.5 (5) | C22—C13—C17—C18 | −159.1 (4) |
C8—C9—C10—O2 | −80.1 (4) | C14—C13—C17—C18 | 83.5 (4) |
C14—C9—C10—C11 | −18.5 (5) | O3—C17—C18—C19 | −23.9 (5) |
C8—C9—C10—C11 | −147.1 (4) | C16—C17—C18—C19 | −140.9 (4) |
C14—C9—C10—C4 | −173.7 (4) | C13—C17—C18—C19 | 97.0 (5) |
C8—C9—C10—C4 | 57.8 (5) | C17—C18—C19—C20 | 23.7 (5) |
C3—C4—C10—O2 | 92.8 (4) | C17—O3—C20—O4 | 176.8 (5) |
C21—C4—C10—O2 | −149.0 (3) | C17—O3—C20—C19 | −1.0 (5) |
C5—C4—C10—O2 | −28.5 (5) | C18—C19—C20—O4 | 167.6 (6) |
C3—C4—C10—C11 | 161.8 (4) | C18—C19—C20—O3 | −14.9 (6) |
C21—C4—C10—C11 | −80.1 (5) | C24—O6—C23—O5 | −3.1 (7) |
C5—C4—C10—C11 | 40.5 (6) | C24—O6—C23—C8 | 177.1 (5) |
C3—C4—C10—C9 | −43.8 (5) | C7—C8—C23—O5 | −163.7 (4) |
C21—C4—C10—C9 | 74.4 (5) | C9—C8—C23—O5 | 72.7 (5) |
C5—C4—C10—C9 | −165.1 (4) | C7—C8—C23—O6 | 16.2 (5) |
C10—O2—C11—C12 | 115.2 (4) | C9—C8—C23—O6 | −107.5 (4) |
C9—C10—C11—O2 | 101.9 (4) | C74—O7—C71—C72 | −22 (3) |
C4—C10—C11—O2 | −104.3 (4) | O7—C71—C72—C73 | 61 (2) |
O2—C10—C11—C12 | −103.6 (4) | C71—C72—C73—C74 | −69.0 (18) |
C9—C10—C11—C12 | −1.7 (6) | C71—O7—C74—C73 | −25 (3) |
C4—C10—C11—C12 | 152.1 (4) | C72—C73—C74—O7 | 59 (2) |
O2—C11—C12—C13 | −80.8 (5) | C84—O8—C81—C82 | 12 (3) |
C10—C11—C12—C13 | −11.4 (6) | O8—C81—C82—C83 | 10 (3) |
C11—C12—C13—C17 | 154.9 (4) | C81—C82—C83—C84 | −26 (3) |
C11—C12—C13—C22 | −79.3 (5) | C81—O8—C84—C83 | −28 (3) |
C11—C12—C13—C14 | 42.6 (5) | C82—C83—C84—O8 | 30 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4i | 0.98 | 2.60 | 3.410 (6) | 140 |
C12—H12B···O1ii | 0.97 | 2.55 | 3.499 (7) | 168 |
C14—H14···O5 | 0.98 | 2.48 | 3.096 (6) | 120 |
C19—H19B···O1ii | 0.97 | 2.58 | 3.240 (7) | 125 |
C21—H21A···O5iii | 0.96 | 2.55 | 3.344 (7) | 141 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2. |