An ethanol solvate of Beclomethasone dipropionate

Kuehl, P.J.; Carducci, M.D.; Myrdal, P.B.

doi:10.1107/S1600536803024425

An ethanol solvate of Beclomethasone dipropionate

P. J. Kuehl, M. D. Carducci and P. B. Myrdal

Beclomethasone dipropionate (BDP) is a widely used corticosteroid formulated in metered dose inhalers (MDI) for the treatment of asthma. The crystal structure of a BDP ethanol solvate of apparent formula C₂₈H₃₇ClO₇·2C₂H₆O has been determined at 170 K. The crystal investigated in this study was grown in a 3% (w/w) saturated solution of 200-proof ethanol (EtOH) at 203 K. Under these conditions, BDP crystallizes with a channel structure that allows for the inclusion of disordered ethanol molecules. The steroid molecules are held in place through intermolecular hydrogen bonding and chlorine-chlorine interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024425/cf6289sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024425/cf6289Isup2.hkl Contains datablock I

CCDC reference: 227863

checkCIF report

Key indicators

Single-crystal X-ray study
T = 170 K
Mean (C-C) = 0.005 Å
R factor = 0.067
wR factor = 0.118
Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level A
CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.90 <> 1.10
           From the CIF: _cell_formula_units_Z                    6
           From the CIF: _chemical_formula_weight           613.16
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   28.00  336.31
           H         1.01   37.00   37.30
           O        16.00    7.00  111.99
           Cl       35.45    1.00   35.45
           Calculated formula weight              521.05
PLAT043_ALERT_1_A Check Reported Molecular Weight ................     613.16
PLAT044_ALERT_1_A Calculated and Reported Dx Differ ..............          ?

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.53 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.28 Ratio

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.133
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Cl1    -   C10      =       5.28 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O7     -   C26      =       5.43 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5       =       5.05 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure        !

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:C32 H49 Cl1 O9
            Atom count from the _atom_site data:  C28 H37 Cl1 O7
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    6
           From the CIF: _chemical_formula_sum  C32 H49 Cl O9
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        192.00    168.00   24.00
           H        294.00    222.00   72.00
           Cl         6.00      6.00    0.00
           O         54.00     42.00   12.00
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           25.56
           From the CIF: _reflns_number_total               6110
           Count of symmetry unique reflns         3470
           Completeness (_total/calc)            176.08%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2640
           Fraction of Friedel pairs measured     0.761
           Are heavy atom types Z>Si present          yes

   3 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

9α-chloro-16β-methyl-3,20-dioxo-1,4-pregnadiene-11β,17,21-triol 17,21-dipropionate top

Crystal data top

C₂₈H₃₇ClO₇·2C₂H₆O	D_x = 1.249 Mg m⁻³
M_r = 613.16	Melting point: 212 K
Trigonal, P3₁21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 31 2"	Cell parameters from 2588 reflections
a = 13.4869 (10) Å	θ = 2.2–17.8°
c = 31.046 (4) Å	µ = 0.17 mm⁻¹
V = 4890.6 (8) Å³	T = 170 K
Z = 6	Block, colorless
F(000) = 1980	0.21 × 0.17 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6110 independent reflections
Radiation source: fine-focus sealed tube	4718 reflections with I > \2(I)
Graphite monochromator	R_int = 0.133
φ and ω scans	θ_max = 25.6°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −16→16
T_min = 0.870, T_max = 0.982	k = −16→16
52513 measured reflections	l = −37→37

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)] = 0.067	H-atom parameters constrained
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0511P)² + 0.134P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.002
6110 reflections	Δρ_max = 0.42 e Å⁻³
325 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2466 Friedel pairs
4 constraints	Absolute structure parameter: 0.04 (8)
Primary atom site location: structure-invariant direct methods

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	U_iso*/U_eq
Cl1	0.89232 (7)	0.43046 (7)	0.12746 (3)	0.0283 (2)
O1	1.2535 (2)	0.6979 (2)	0.05115 (9)	0.0489 (7)
C1	1.1490 (3)	0.6415 (3)	0.05108 (11)	0.0337 (9)
O2	0.68260 (18)	0.50289 (19)	0.06488 (7)	0.0297 (6)
H2A	0.6494	0.5367	0.0747	0.045*
C2	1.0766 (3)	0.6892 (3)	0.06367 (11)	0.0340 (9)
H2B	1.1116	0.7665	0.0730	0.041*
O3	0.55391 (17)	0.19436 (17)	0.18353 (6)	0.0216 (5)
C3	0.9627 (3)	0.6264 (3)	0.06231 (11)	0.0311 (9)
H3A	0.9201	0.6603	0.0726	0.037*
O4	0.4203 (2)	0.0338 (2)	0.21608 (7)	0.0306 (6)
C4	0.8983 (3)	0.5078 (3)	0.04594 (10)	0.0240 (8)
O5	0.29414 (19)	0.10692 (19)	0.12864 (8)	0.0341 (6)
C5	0.9744 (3)	0.4569 (3)	0.03561 (10)	0.0271 (8)
O6	0.2712 (2)	0.2376 (2)	0.18678 (8)	0.0369 (6)
C6	1.0878 (3)	0.5212 (3)	0.03724 (10)	0.0301 (8)
H6A	1.1319	0.4872	0.0290	0.036*
O7	0.3413 (2)	0.3580 (2)	0.13101 (8)	0.0362 (6)
C7	0.9150 (3)	0.3363 (3)	0.02029 (10)	0.0264 (8)
H7A	0.9717	0.3105	0.0173	0.032*
H7B	0.8817	0.3325	−0.0085	0.032*
C8	0.8202 (3)	0.2557 (3)	0.05087 (10)	0.0269 (8)
H8A	0.8553	0.2438	0.0769	0.032*
H8B	0.7741	0.1805	0.0366	0.032*
C9	0.7406 (3)	0.3016 (3)	0.06449 (10)	0.0224 (8)
H9A	0.6965	0.3000	0.0384	0.027*
C10	0.8070 (3)	0.4257 (3)	0.08008 (10)	0.0234 (8)
C11	0.8415 (3)	0.5114 (3)	0.00285 (11)	0.0338 (9)
H11A	0.9007	0.5630	−0.0174	0.051*
H11B	0.7879	0.5391	0.0083	0.051*
H11C	0.8000	0.4343	−0.0095	0.051*
C12	0.7287 (3)	0.4690 (3)	0.09974 (10)	0.0226 (8)
H12A	0.7785	0.5390	0.1172	0.027*
C13	0.6343 (3)	0.3819 (3)	0.12970 (10)	0.0239 (8)
H13A	0.6697	0.3783	0.1572	0.029*
H13B	0.5802	0.4093	0.1363	0.029*
C14	0.5670 (3)	0.2608 (3)	0.11073 (9)	0.0201 (7)
C15	0.6540 (3)	0.2235 (3)	0.09792 (10)	0.0210 (8)
H15A	0.6983	0.2288	0.1245	0.025*
C16	0.4922 (3)	0.2548 (3)	0.07234 (10)	0.0293 (9)
H16A	0.5385	0.3161	0.0519	0.044*
H16B	0.4286	0.2642	0.0826	0.044*
H16C	0.4617	0.1804	0.0580	0.044*
C17	0.5776 (3)	0.0962 (3)	0.08802 (10)	0.0262 (8)
H17A	0.6224	0.0562	0.0884	0.031*
H17B	0.5405	0.0849	0.0595	0.031*
C18	0.4876 (3)	0.0520 (3)	0.12460 (10)	0.0255 (8)
H18A	0.5181	0.0233	0.1479	0.031*
C19	0.4905 (3)	0.1619 (3)	0.14289 (9)	0.0210 (7)
C20	0.3729 (3)	−0.0496 (3)	0.11083 (11)	0.0350 (9)
H20A	0.3848	−0.1112	0.1002	0.052*
H20B	0.3395	−0.0255	0.0879	0.052*
H20C	0.3208	−0.0771	0.1356	0.052*
C21	0.5107 (3)	0.1232 (3)	0.21735 (10)	0.0247 (8)
C22	0.5846 (3)	0.1732 (3)	0.25576 (10)	0.0337 (9)
H22A	0.5855	0.2447	0.2637	0.040*
H22B	0.6639	0.1937	0.2481	0.040*
C23	0.5474 (4)	0.0951 (3)	0.29427 (11)	0.0498 (11)
H23A	0.6000	0.1336	0.3183	0.075*
H23B	0.5483	0.0248	0.2870	0.075*
H23C	0.4698	0.0759	0.3026	0.075*
C24	0.3767 (3)	0.1584 (3)	0.15117 (11)	0.0250 (8)
C25	0.3744 (3)	0.2327 (3)	0.18813 (11)	0.0335 (9)
H25A	0.3798	0.2002	0.2160	0.040*
H25B	0.4411	0.3110	0.1857	0.040*
C26	0.2632 (3)	0.2988 (3)	0.15427 (12)	0.0328 (9)
C27	0.1444 (3)	0.2815 (4)	0.15234 (13)	0.0487 (11)
H27A	0.0903	0.1996	0.1463	0.058*
H27B	0.1250	0.2989	0.1811	0.058*
C28	0.1264 (4)	0.3508 (4)	0.12004 (15)	0.0714 (15)
H28A	0.0468	0.3336	0.1212	0.107*
H28B	0.1429	0.3328	0.0913	0.107*
H28C	0.1776	0.4323	0.1261	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0283 (5)	0.0310 (5)	0.0262 (4)	0.0154 (4)	−0.0061 (4)	−0.0006 (4)
O1	0.0182 (15)	0.0457 (17)	0.0714 (19)	0.0073 (14)	0.0032 (14)	0.0051 (15)
C1	0.024 (2)	0.039 (2)	0.033 (2)	0.012 (2)	0.0023 (17)	0.0117 (18)
O2	0.0330 (14)	0.0355 (14)	0.0320 (13)	0.0257 (12)	0.0088 (11)	0.0129 (12)
C2	0.028 (2)	0.024 (2)	0.044 (2)	0.0082 (18)	0.0035 (18)	0.0004 (17)
O3	0.0255 (13)	0.0197 (12)	0.0142 (11)	0.0073 (11)	0.0025 (10)	0.0018 (10)
C3	0.033 (2)	0.025 (2)	0.037 (2)	0.0160 (18)	0.0042 (17)	0.0031 (17)
O4	0.0308 (14)	0.0273 (14)	0.0289 (13)	0.0109 (13)	0.0037 (11)	0.0035 (11)
C4	0.0177 (18)	0.034 (2)	0.0251 (18)	0.0165 (16)	0.0040 (15)	0.0072 (16)
O5	0.0238 (14)	0.0320 (14)	0.0402 (15)	0.0092 (12)	−0.0011 (12)	0.0002 (12)
C5	0.028 (2)	0.036 (2)	0.0157 (17)	0.0146 (18)	0.0043 (15)	0.0017 (15)
O6	0.0316 (15)	0.0433 (16)	0.0407 (15)	0.0225 (13)	0.0127 (12)	0.0085 (13)
C6	0.034 (2)	0.036 (2)	0.0307 (19)	0.025 (2)	0.0064 (16)	0.0053 (17)
O7	0.0255 (14)	0.0377 (15)	0.0489 (15)	0.0183 (13)	0.0091 (13)	0.0109 (13)
C7	0.028 (2)	0.030 (2)	0.0268 (19)	0.0188 (17)	0.0060 (16)	0.0028 (16)
C8	0.031 (2)	0.029 (2)	0.0253 (18)	0.0184 (17)	0.0003 (15)	−0.0001 (15)
C9	0.0212 (18)	0.0231 (19)	0.0222 (17)	0.0106 (16)	0.0003 (15)	0.0012 (15)
C10	0.0234 (19)	0.035 (2)	0.0191 (17)	0.0204 (17)	−0.0077 (15)	−0.0015 (15)
C11	0.029 (2)	0.042 (2)	0.032 (2)	0.0188 (19)	0.0121 (17)	0.0157 (18)
C12	0.028 (2)	0.0222 (18)	0.0198 (17)	0.0147 (16)	0.0009 (15)	0.0005 (14)
C13	0.031 (2)	0.0242 (19)	0.0224 (17)	0.0181 (16)	0.0042 (16)	0.0010 (15)
C14	0.0235 (18)	0.0172 (17)	0.0166 (16)	0.0080 (15)	−0.0005 (14)	0.0007 (14)
C15	0.031 (2)	0.0233 (19)	0.0149 (16)	0.0182 (17)	−0.0014 (15)	0.0010 (14)
C16	0.030 (2)	0.035 (2)	0.030 (2)	0.0208 (18)	0.0040 (16)	0.0072 (16)
C17	0.031 (2)	0.029 (2)	0.0211 (18)	0.0162 (17)	−0.0002 (16)	−0.0049 (15)
C18	0.031 (2)	0.0244 (19)	0.0224 (18)	0.0152 (17)	−0.0057 (15)	−0.0033 (15)
C19	0.0260 (19)	0.0166 (17)	0.0179 (17)	0.0088 (15)	−0.0010 (15)	−0.0024 (14)
C20	0.035 (2)	0.026 (2)	0.036 (2)	0.0088 (18)	−0.0010 (18)	−0.0073 (17)
C21	0.031 (2)	0.0162 (19)	0.028 (2)	0.0128 (17)	0.0029 (17)	−0.0003 (16)
C22	0.042 (2)	0.025 (2)	0.0236 (19)	0.0095 (18)	−0.0048 (18)	−0.0037 (16)
C23	0.076 (3)	0.043 (2)	0.0211 (18)	0.022 (2)	−0.012 (2)	−0.0010 (19)
C24	0.024 (2)	0.0199 (19)	0.0290 (19)	0.0091 (16)	0.0025 (16)	0.0074 (16)
C25	0.032 (2)	0.038 (2)	0.036 (2)	0.0219 (19)	0.0044 (17)	0.0068 (18)
C26	0.029 (2)	0.033 (2)	0.040 (2)	0.018 (2)	−0.0042 (19)	−0.007 (2)
C27	0.033 (2)	0.061 (3)	0.054 (3)	0.025 (2)	−0.003 (2)	−0.005 (2)
C28	0.056 (3)	0.091 (4)	0.080 (4)	0.047 (3)	0.008 (3)	0.023 (3)

Geometric parameters (Å, º) top

Cl1—C10	1.849 (3)	C13—C14	1.534 (4)
O1—C1	1.222 (4)	C13—H13A	0.990
C1—C2	1.465 (5)	C13—H13B	0.990
C1—C6	1.470 (5)	C14—C16	1.537 (4)
O2—C12	1.432 (4)	C14—C15	1.543 (4)
O2—H2A	0.840	C14—C19	1.570 (4)
C2—C3	1.333 (5)	C15—C17	1.529 (4)
C2—H2B	0.950	C15—H15A	1.000
O3—C21	1.343 (4)	C16—H16A	0.980
O3—C19	1.463 (3)	C16—H16B	0.980
C3—C4	1.477 (5)	C16—H16C	0.980
C3—H3A	0.950	C17—C18	1.548 (4)
O4—C21	1.213 (4)	C17—H17A	0.990
C4—C5	1.526 (5)	C17—H17B	0.990
C4—C11	1.555 (5)	C18—C20	1.527 (4)
C4—C10	1.582 (4)	C18—C19	1.569 (4)
O5—C24	1.200 (4)	C18—H18A	1.000
C5—C6	1.329 (5)	C19—C24	1.533 (4)
C5—C7	1.487 (4)	C20—H20A	0.980
O6—C26	1.342 (4)	C20—H20B	0.980
O6—C25	1.426 (4)	C20—H20C	0.980
C6—H6A	0.950	C21—C22	1.483 (4)
O7—C26	1.194 (4)	C22—C23	1.504 (5)
C7—C8	1.526 (4)	C22—H22A	0.990
C7—H7A	0.990	C22—H22B	0.990
C7—H7B	0.990	C23—H23A	0.980
C8—C9	1.543 (4)	C23—H23B	0.980
C8—H8A	0.990	C23—H23C	0.980
C8—H8B	0.990	C24—C25	1.534 (5)
C9—C15	1.523 (4)	C25—H25A	0.990
C9—C10	1.530 (4)	C25—H25B	0.990
C9—H9A	1.000	C26—C27	1.501 (5)
C10—C12	1.564 (4)	C27—C28	1.472 (5)
C11—H11A	0.980	C27—H27A	0.990
C11—H11B	0.980	C27—H27B	0.990
C11—H11C	0.980	C28—H28A	0.980
C12—C13	1.540 (4)	C28—H28B	0.980
C12—H12A	1.000	C28—H28C	0.980

O1—C1—C2	122.8 (3)	C17—C15—C14	102.9 (3)
O1—C1—C6	121.6 (3)	C9—C15—H15A	106.8
C2—C1—C6	115.6 (3)	C17—C15—H15A	106.8
C12—O2—H2A	109.5	C14—C15—H15A	106.8
C3—C2—C1	121.5 (3)	C14—C16—H16A	109.5
C3—C2—H2B	119.3	C14—C16—H16B	109.5
C1—C2—H2B	119.3	H16A—C16—H16B	109.5
C21—O3—C19	118.7 (2)	C14—C16—H16C	109.5
C2—C3—C4	124.4 (3)	H16A—C16—H16C	109.5
C2—C3—H3A	117.8	H16B—C16—H16C	109.5
C4—C3—H3A	117.8	C15—C17—C18	104.1 (2)
C3—C4—C5	113.3 (3)	C15—C17—H17A	110.9
C3—C4—C11	107.1 (3)	C18—C17—H17A	110.9
C5—C4—C11	106.6 (3)	C15—C17—H17B	110.9
C3—C4—C10	111.0 (3)	C18—C17—H17B	110.9
C5—C4—C10	106.8 (3)	H17A—C17—H17B	109.0
C11—C4—C10	112.0 (3)	C20—C18—C17	112.8 (3)
C6—C5—C7	122.7 (3)	C20—C18—C19	118.9 (3)
C6—C5—C4	120.8 (3)	C17—C18—C19	104.9 (2)
C7—C5—C4	116.4 (3)	C20—C18—H18A	106.5
C26—O6—C25	115.5 (3)	C17—C18—H18A	106.5
C5—C6—C1	124.0 (3)	C19—C18—H18A	106.5
C5—C6—H6A	118.0	O3—C19—C24	106.9 (2)
C1—C6—H6A	118.0	O3—C19—C18	109.2 (2)
C5—C7—C8	112.4 (3)	C24—C19—C18	118.7 (3)
C5—C7—H7A	109.1	O3—C19—C14	104.9 (2)
C8—C7—H7A	109.1	C24—C19—C14	110.8 (3)
C5—C7—H7B	109.1	C18—C19—C14	105.6 (2)
C8—C7—H7B	109.1	C18—C20—H20A	109.5
H7A—C7—H7B	107.8	C18—C20—H20B	109.5
C7—C8—C9	112.8 (3)	H20A—C20—H20B	109.5
C7—C8—H8A	109.0	C18—C20—H20C	109.5
C9—C8—H8A	109.0	H20A—C20—H20C	109.5
C7—C8—H8B	109.0	H20B—C20—H20C	109.5
C9—C8—H8B	109.0	O4—C21—O3	123.1 (3)
H8A—C8—H8B	107.8	O4—C21—C22	126.2 (3)
C15—C9—C10	111.6 (2)	O3—C21—C22	110.5 (3)
C15—C9—C8	110.9 (3)	C21—C22—C23	114.1 (3)
C10—C9—C8	112.4 (3)	C21—C22—H22A	108.7
C15—C9—H9A	107.2	C23—C22—H22A	108.7
C10—C9—H9A	107.2	C21—C22—H22B	108.7
C8—C9—H9A	107.2	C23—C22—H22B	108.7
C9—C10—C12	113.4 (3)	H22A—C22—H22B	107.6
C9—C10—C4	112.3 (3)	C22—C23—H23A	109.5
C12—C10—C4	115.8 (3)	C22—C23—H23B	109.5
C9—C10—Cl1	107.6 (2)	H23A—C23—H23B	109.5
C12—C10—Cl1	101.6 (2)	C22—C23—H23C	109.5
C4—C10—Cl1	104.8 (2)	H23A—C23—H23C	109.5
C4—C11—H11A	109.5	H23B—C23—H23C	109.5
C4—C11—H11B	109.5	O5—C24—C19	123.0 (3)
H11A—C11—H11B	109.5	O5—C24—C25	119.9 (3)
C4—C11—H11C	109.5	C19—C24—C25	116.9 (3)
H11A—C11—H11C	109.5	O6—C25—C24	110.3 (3)
H11B—C11—H11C	109.5	O6—C25—H25A	109.6
O2—C12—C13	112.0 (3)	C24—C25—H25A	109.6
O2—C12—C10	107.8 (2)	O6—C25—H25B	109.6
C13—C12—C10	113.9 (3)	C24—C25—H25B	109.6
O2—C12—H12A	107.6	H25A—C25—H25B	108.1
C13—C12—H12A	107.6	O7—C26—O6	123.4 (3)
C10—C12—H12A	107.6	O7—C26—C27	126.5 (4)
C14—C13—C12	113.8 (2)	O6—C26—C27	110.0 (3)
C14—C13—H13A	108.8	C28—C27—C26	115.5 (4)
C12—C13—H13A	108.8	C28—C27—H27A	108.4
C14—C13—H13B	108.8	C26—C27—H27A	108.4
C12—C13—H13B	108.8	C28—C27—H27B	108.4
H13A—C13—H13B	107.7	C26—C27—H27B	108.4
C13—C14—C16	112.2 (3)	H27A—C27—H27B	107.5
C13—C14—C15	107.7 (2)	C27—C28—H28A	109.5
C16—C14—C15	111.7 (3)	C27—C28—H28B	109.5
C13—C14—C19	116.6 (2)	H28A—C28—H28B	109.5
C16—C14—C19	108.3 (2)	C27—C28—H28C	109.5
C15—C14—C19	99.8 (2)	H28A—C28—H28C	109.5
C9—C15—C17	119.5 (3)	H28B—C28—H28C	109.5
C9—C15—C14	113.3 (3)

O1—C1—C2—C3	178.4 (4)	C8—C9—C15—C17	−54.8 (4)
C6—C1—C2—C3	−0.3 (5)	C10—C9—C15—C14	57.5 (3)
C1—C2—C3—C4	−3.9 (6)	C8—C9—C15—C14	−176.4 (3)
C2—C3—C4—C5	7.2 (5)	C13—C14—C15—C9	−60.2 (3)
C2—C3—C4—C11	−110.1 (4)	C16—C14—C15—C9	63.4 (3)
C2—C3—C4—C10	127.4 (4)	C19—C14—C15—C9	177.7 (2)
C3—C4—C5—C6	−6.9 (4)	C13—C14—C15—C17	169.4 (2)
C11—C4—C5—C6	110.7 (3)	C16—C14—C15—C17	−67.0 (3)
C10—C4—C5—C6	−129.4 (3)	C19—C14—C15—C17	47.2 (3)
C3—C4—C5—C7	178.1 (3)	C9—C15—C17—C18	−169.2 (3)
C11—C4—C5—C7	−64.3 (4)	C14—C15—C17—C18	−42.6 (3)
C10—C4—C5—C7	55.6 (3)	C15—C17—C18—C20	150.9 (3)
C7—C5—C6—C1	178.2 (3)	C15—C17—C18—C19	19.9 (3)
C4—C5—C6—C1	3.6 (5)	C21—O3—C19—C24	64.4 (3)
O1—C1—C6—C5	−178.4 (3)	C21—O3—C19—C18	−65.2 (3)
C2—C1—C6—C5	0.3 (5)	C21—O3—C19—C14	−178.0 (2)
C6—C5—C7—C8	131.5 (3)	C20—C18—C19—O3	129.8 (3)
C4—C5—C7—C8	−53.6 (4)	C17—C18—C19—O3	−102.9 (3)
C5—C7—C8—C9	47.7 (4)	C20—C18—C19—C24	7.0 (4)
C7—C8—C9—C15	−175.1 (3)	C17—C18—C19—C24	134.3 (3)
C7—C8—C9—C10	−49.3 (4)	C20—C18—C19—C14	−117.9 (3)
C15—C9—C10—C12	−47.0 (3)	C17—C18—C19—C14	9.4 (3)
C8—C9—C10—C12	−172.4 (2)	C13—C14—C19—O3	−34.6 (3)
C15—C9—C10—C4	179.4 (2)	C16—C14—C19—O3	−162.2 (2)
C8—C9—C10—C4	54.1 (3)	C15—C14—C19—O3	80.9 (3)
C15—C9—C10—Cl1	64.5 (3)	C13—C14—C19—C24	80.3 (3)
C8—C9—C10—Cl1	−60.8 (3)	C16—C14—C19—C24	−47.2 (3)
C3—C4—C10—C9	−178.7 (3)	C15—C14—C19—C24	−164.1 (3)
C5—C4—C10—C9	−54.8 (3)	C13—C14—C19—C18	−150.0 (3)
C11—C4—C10—C9	61.6 (3)	C16—C14—C19—C18	82.5 (3)
C3—C4—C10—C12	48.9 (3)	C15—C14—C19—C18	−34.4 (3)
C5—C4—C10—C12	172.8 (3)	C19—O3—C21—O4	−1.3 (4)
C11—C4—C10—C12	−70.8 (3)	C19—O3—C21—C22	−177.7 (3)
C3—C4—C10—Cl1	−62.2 (3)	O4—C21—C22—C23	8.2 (5)
C5—C4—C10—Cl1	61.8 (3)	O3—C21—C22—C23	−175.5 (3)
C11—C4—C10—Cl1	178.1 (2)	O3—C19—C24—O5	−159.7 (3)
C9—C10—C12—O2	−82.0 (3)	C18—C19—C24—O5	−35.7 (4)
C4—C10—C12—O2	49.9 (3)	C14—C19—C24—O5	86.6 (4)
Cl1—C10—C12—O2	162.8 (2)	O3—C19—C24—C25	25.1 (4)
C9—C10—C12—C13	43.0 (4)	C18—C19—C24—C25	149.1 (3)
C4—C10—C12—C13	174.9 (3)	C14—C19—C24—C25	−88.6 (3)
Cl1—C10—C12—C13	−72.2 (3)	C26—O6—C25—C24	−71.0 (4)
O2—C12—C13—C14	74.8 (3)	O5—C24—C25—O6	−6.2 (4)
C10—C12—C13—C14	−47.9 (4)	C19—C24—C25—O6	169.1 (3)
C12—C13—C14—C16	−68.5 (3)	C25—O6—C26—O7	−9.4 (5)
C12—C13—C14—C15	54.7 (3)	C25—O6—C26—C27	170.9 (3)
C12—C13—C14—C19	165.8 (3)	O7—C26—C27—C28	−4.1 (6)
C10—C9—C15—C17	179.0 (3)	O6—C26—C27—C28	175.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O4ⁱ	0.84	2.16	2.978 (3)	164

Symmetry code: (i) −x+1, −x+y+1, −z+1/3.

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