Eplerenone tetra­hydro­furan solvate

The eplerenone mol­ecule of the title compound, C₂₄H₃₀O₆·C₄H₈O, 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 ų cavity, which is occupied by two disordered solvent THF mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

---

Computing details

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).

9α,11-Epoxy-7α-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone

Crystal data

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) Å^3	Block, colorless
Z = 4	0.32 × 0.19 × 0.13 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.070	H-atom parameters constrained
wR(F^2) = 0.229	w = 1/[σ^2(Fo^2) + (0.1455P)^2 + 0.1324P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (7)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4^i	0.98	2.60	3.410 (6)	140
C12—H12B···O1^ii	0.97	2.55	3.499 (7)	168
C14—H14···O5	0.98	2.48	3.096 (6)	120
C19—H19B···O1^ii	0.97	2.58	3.240 (7)	125
C21—H21A···O5^iii	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.