Triamcinolone diacetate chloro­form solvate

In the crystal structure of the title compound, 16α,21-diacet­oxy-9α-fluoro-11β,17α-dihydr­oxy-1,4-pregnadiene-3,20-dione chloro­form solvate, C₂₅H₃₁FO₈·CHCl₃, the mol­ecules are connected via O—H...O hydrogen bonding. Channels, in which the chloro­form mol­ecules are located, are formed in the direction of the crystallographic a axis.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.122
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O6     ..  C24     ..       2.88 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.81 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.17 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C26
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C23
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  O4      ..       3.05 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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           27.10
           From the CIF: _reflns_number_total               6150
           Count of symmetry unique reflns         3492
           Completeness (_total/calc)            176.12%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2658
           Fraction of Friedel pairs measured     0.761
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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Computing details

Data collection: IPDS Program Package (Stoe & Cie, 1998); cell refinement: IPDS Program Package; data reduction: IPDS Program Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: CIFTAB in SHELXTL.

16α,21-diacetoxy-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione chloroform solvate

Crystal data

C25H31FO8·CHCl3	F(000) = 1248
Mr = 597.87	Dx = 1.424 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8000 reflections
a = 8.0465 (4) Å	θ = 11.6–25°
b = 14.5972 (7) Å	µ = 0.38 mm^−1
c = 23.7454 (14) Å	T = 170 K
V = 2789.0 (3) Å^3	Block, colourless
Z = 4	0.2 × 0.2 × 0.15 mm

Data collection

IPDS-1 diffractometer	4683 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Graphite monochromator	θmax = 27.1°, θmin = 2.7°
φ scans	h = −10→8
17821 measured reflections	k = −18→16
6150 independent reflections	l = −30→30

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 1.0803P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.59 e Å^−3
6150 reflections	Δρmin = −0.45 e Å^−3
347 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0083 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.06 (8)

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
O1	−0.0183 (4)	0.97252 (17)	0.45783 (8)	0.0456 (7)
O2	0.1598 (3)	0.84146 (16)	0.72423 (8)	0.0290 (5)
H1O2	0.2269	0.8510	0.7507	0.043*
O3	0.5455 (2)	0.57657 (13)	0.65175 (7)	0.0202 (4)
H1O3	0.5024	0.5550	0.6224	0.030*
O4	0.4981 (3)	0.52941 (15)	0.79451 (7)	0.0287 (5)
O5	0.8104 (3)	0.60134 (14)	0.79262 (8)	0.0275 (5)
O6	0.6813 (4)	0.73584 (19)	0.79491 (11)	0.0570 (8)
O7	0.3769 (3)	0.42113 (13)	0.64608 (7)	0.0218 (4)
O8	0.5966 (3)	0.38785 (14)	0.69968 (8)	0.0303 (5)
F1	0.2131 (2)	0.77127 (11)	0.58201 (6)	0.0221 (4)
C1	−0.0230 (4)	0.9364 (2)	0.50524 (10)	0.0266 (7)
C2	0.0622 (4)	0.9803 (2)	0.55238 (11)	0.0281 (6)
H2	0.1179	1.0370	0.5467	0.034*
C3	0.0628 (4)	0.9421 (2)	0.60301 (11)	0.0257 (6)
H3	0.1189	0.9734	0.6325	0.031*
C4	−0.0190 (4)	0.85279 (19)	0.61684 (10)	0.0204 (6)
C5	0.1182 (4)	0.78061 (19)	0.63230 (10)	0.0184 (6)
C6	0.2486 (4)	0.81372 (19)	0.67543 (11)	0.0218 (6)
H6	0.3056	0.8688	0.6594	0.026*
C7	0.3805 (4)	0.7411 (2)	0.68746 (11)	0.0215 (6)
H7A	0.4530	0.7349	0.6540	0.026*
H7B	0.4505	0.7621	0.7192	0.026*
C8	0.3089 (3)	0.64724 (19)	0.70195 (10)	0.0181 (5)
C9	0.4345 (4)	0.56541 (19)	0.69759 (10)	0.0190 (5)
C10	0.3171 (3)	0.4810 (2)	0.68987 (10)	0.0202 (5)
H10	0.3042	0.4470	0.7261	0.024*
C11	0.1487 (4)	0.5187 (2)	0.66976 (12)	0.0240 (6)
H11A	0.1085	0.4850	0.6363	0.029*
H11B	0.0641	0.5146	0.6999	0.029*
C12	0.1872 (3)	0.61828 (19)	0.65535 (11)	0.0197 (5)
H12	0.2534	0.6167	0.6197	0.024*
C13	0.0456 (4)	0.68581 (18)	0.64507 (11)	0.0197 (5)
H13	−0.0228	0.6901	0.6801	0.024*
C14	−0.0660 (4)	0.6519 (2)	0.59694 (12)	0.0262 (6)
H14A	0.0048	0.6350	0.5645	0.031*
H14B	−0.1251	0.5960	0.6095	0.031*
C15	−0.1946 (4)	0.7228 (2)	0.57750 (14)	0.0306 (7)
H15A	−0.2489	0.7013	0.5425	0.037*
H15B	−0.2814	0.7300	0.6067	0.037*
C16	−0.1121 (4)	0.8130 (2)	0.56707 (11)	0.0238 (6)
C17	−0.1103 (4)	0.8522 (2)	0.51639 (11)	0.0267 (6)
H17	−0.1688	0.8234	0.4865	0.032*
C18	−0.1447 (4)	0.8721 (2)	0.66478 (12)	0.0333 (8)
H18A	−0.2015	0.8152	0.6751	0.050*
H18B	−0.2267	0.9172	0.6519	0.050*
H18C	−0.0855	0.8964	0.6976	0.050*
C19	0.2264 (4)	0.6485 (2)	0.76054 (11)	0.0264 (6)
H19A	0.1813	0.5876	0.7690	0.040*
H19B	0.1363	0.6936	0.7608	0.040*
H19C	0.3093	0.6650	0.7890	0.040*
C20	0.5476 (4)	0.55670 (19)	0.74946 (10)	0.0205 (5)
C21	0.7262 (4)	0.5850 (2)	0.74056 (11)	0.0261 (6)
H21A	0.7850	0.5363	0.7195	0.031*
H21B	0.7292	0.6415	0.7175	0.031*
C22	0.7784 (4)	0.6843 (2)	0.81543 (12)	0.0317 (7)
C23	0.8769 (6)	0.7002 (3)	0.86730 (16)	0.0507 (11)
H23A	0.9478	0.6469	0.8746	0.076*
H23B	0.8015	0.7094	0.8992	0.076*
H23C	0.9463	0.7547	0.8624	0.076*
C24	0.5208 (4)	0.37819 (19)	0.65628 (11)	0.0245 (6)
C25	0.5737 (5)	0.3199 (2)	0.60850 (13)	0.0371 (8)
H25A	0.6830	0.2935	0.6166	0.056*
H25B	0.5803	0.3571	0.5742	0.056*
H25C	0.4928	0.2705	0.6030	0.056*
Cl1	0.75360 (18)	0.16996 (9)	0.50858 (5)	0.0702 (4)
Cl2	0.43668 (17)	0.10105 (11)	0.47032 (5)	0.0741 (4)
Cl3	0.56404 (19)	0.04954 (9)	0.57946 (5)	0.0718 (4)
C26	0.6164 (6)	0.0769 (3)	0.50941 (17)	0.0529 (10)
H26	0.6733	0.0229	0.4921	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.082 (2)	0.0385 (13)	0.0167 (9)	0.0030 (14)	−0.0052 (11)	0.0058 (9)
O2	0.0291 (12)	0.0355 (12)	0.0224 (9)	0.0079 (11)	−0.0059 (8)	−0.0120 (9)
O3	0.0188 (10)	0.0264 (10)	0.0155 (8)	−0.0011 (9)	0.0042 (7)	0.0004 (7)
O4	0.0309 (11)	0.0395 (12)	0.0157 (8)	−0.0026 (10)	0.0011 (8)	0.0043 (8)
O5	0.0278 (11)	0.0256 (11)	0.0292 (10)	0.0027 (9)	−0.0103 (9)	−0.0017 (8)
O6	0.076 (2)	0.0403 (15)	0.0551 (15)	0.0257 (15)	−0.0329 (15)	−0.0143 (12)
O7	0.0268 (11)	0.0192 (10)	0.0194 (8)	0.0018 (9)	−0.0039 (7)	0.0008 (7)
O8	0.0336 (13)	0.0258 (11)	0.0316 (10)	0.0037 (10)	−0.0097 (9)	0.0051 (9)
F1	0.0242 (9)	0.0244 (8)	0.0176 (7)	0.0001 (7)	0.0066 (6)	−0.0035 (6)
C1	0.0377 (18)	0.0264 (14)	0.0159 (11)	0.0077 (14)	−0.0023 (11)	−0.0012 (10)
C2	0.0373 (17)	0.0251 (15)	0.0220 (12)	−0.0019 (15)	−0.0031 (12)	−0.0003 (11)
C3	0.0357 (17)	0.0217 (13)	0.0197 (12)	0.0014 (14)	−0.0078 (12)	−0.0044 (10)
C4	0.0252 (15)	0.0199 (13)	0.0161 (11)	0.0041 (13)	0.0007 (10)	−0.0022 (10)
C5	0.0193 (14)	0.0227 (14)	0.0132 (11)	0.0017 (12)	0.0041 (10)	−0.0024 (9)
C6	0.0227 (15)	0.0197 (13)	0.0231 (12)	0.0001 (13)	−0.0006 (11)	−0.0027 (10)
C7	0.0198 (14)	0.0225 (14)	0.0221 (12)	−0.0023 (12)	0.0009 (10)	−0.0022 (10)
C8	0.0178 (13)	0.0201 (13)	0.0163 (11)	0.0005 (11)	0.0020 (10)	0.0002 (10)
C9	0.0208 (13)	0.0221 (13)	0.0140 (11)	−0.0032 (12)	0.0040 (10)	0.0018 (10)
C10	0.0209 (13)	0.0228 (13)	0.0169 (11)	−0.0007 (12)	0.0019 (10)	0.0001 (10)
C11	0.0192 (14)	0.0203 (13)	0.0325 (14)	−0.0037 (12)	−0.0014 (11)	0.0022 (11)
C12	0.0180 (13)	0.0204 (13)	0.0206 (12)	−0.0018 (12)	0.0004 (10)	0.0001 (10)
C13	0.0171 (13)	0.0193 (13)	0.0226 (12)	−0.0008 (12)	−0.0008 (10)	0.0008 (10)
C14	0.0217 (15)	0.0238 (14)	0.0330 (14)	0.0011 (13)	−0.0068 (12)	−0.0016 (12)
C15	0.0224 (16)	0.0321 (16)	0.0372 (15)	−0.0016 (14)	−0.0083 (13)	0.0039 (13)
C16	0.0188 (14)	0.0250 (14)	0.0275 (13)	0.0048 (12)	−0.0046 (11)	−0.0028 (11)
C17	0.0343 (17)	0.0275 (15)	0.0184 (12)	0.0055 (14)	−0.0105 (11)	−0.0056 (11)
C18	0.0312 (18)	0.046 (2)	0.0230 (13)	0.0150 (16)	0.0029 (12)	0.0032 (13)
C19	0.0268 (16)	0.0310 (15)	0.0212 (12)	0.0019 (14)	0.0068 (11)	−0.0010 (11)
C20	0.0208 (14)	0.0195 (13)	0.0211 (12)	0.0000 (12)	0.0012 (11)	0.0000 (10)
C21	0.0188 (14)	0.0336 (16)	0.0258 (13)	−0.0017 (13)	−0.0015 (11)	−0.0034 (11)
C22	0.0341 (18)	0.0294 (17)	0.0316 (15)	0.0021 (15)	−0.0049 (13)	−0.0036 (12)
C23	0.066 (3)	0.044 (2)	0.0424 (19)	0.000 (2)	−0.0219 (19)	−0.0143 (16)
C24	0.0287 (16)	0.0181 (13)	0.0268 (13)	0.0004 (13)	−0.0019 (12)	0.0052 (11)
C25	0.043 (2)	0.0351 (18)	0.0332 (15)	0.0094 (18)	0.0031 (15)	−0.0038 (13)
Cl1	0.0775 (9)	0.0749 (8)	0.0581 (6)	−0.0044 (7)	0.0235 (6)	−0.0096 (5)
Cl2	0.0620 (7)	0.1045 (10)	0.0557 (6)	0.0281 (8)	−0.0016 (5)	0.0062 (6)
Cl3	0.0846 (9)	0.0693 (7)	0.0616 (6)	0.0121 (7)	0.0006 (6)	0.0265 (5)
C26	0.054 (3)	0.051 (2)	0.054 (2)	0.020 (2)	0.0065 (18)	−0.0024 (18)

Geometric parameters (Å, º)

O1—C1	1.244 (3)	C11—C12	1.525 (4)
O2—C6	1.421 (3)	C11—H11A	0.9900
O2—H1O2	0.8400	C11—H11B	0.9900
O3—C9	1.418 (3)	C12—C13	1.527 (4)
O3—H1O3	0.8400	C12—H12	1.0000
O4—C20	1.209 (3)	C13—C14	1.535 (4)
O5—C22	1.351 (4)	C13—H13	1.0000
O5—C21	1.430 (3)	C14—C15	1.534 (4)
O6—C22	1.189 (4)	C14—H14A	0.9900
O7—C24	1.338 (4)	C14—H14B	0.9900
O7—C10	1.441 (3)	C15—C16	1.496 (4)
O8—C24	1.206 (3)	C15—H15A	0.9900
F1—C5	1.424 (3)	C15—H15B	0.9900
C1—C17	1.441 (5)	C16—C17	1.332 (4)
C1—C2	1.461 (4)	C17—H17	0.9500
C2—C3	1.326 (4)	C18—H18A	0.9800
C2—H2	0.9500	C18—H18B	0.9800
C3—C4	1.497 (4)	C18—H18C	0.9800
C3—H3	0.9500	C19—H19A	0.9800
C4—C16	1.515 (4)	C19—H19B	0.9800
C4—C18	1.549 (4)	C19—H19C	0.9800
C4—C5	1.570 (4)	C20—C21	1.510 (4)
C5—C13	1.533 (4)	C21—H21A	0.9900
C5—C6	1.544 (4)	C21—H21B	0.9900
C6—C7	1.527 (4)	C22—C23	1.483 (5)
C6—H6	1.0000	C23—H23A	0.9800
C7—C8	1.525 (4)	C23—H23B	0.9800
C7—H7A	0.9900	C23—H23C	0.9800
C7—H7B	0.9900	C24—C25	1.480 (4)
C8—C12	1.537 (4)	C25—H25A	0.9800
C8—C19	1.542 (3)	C25—H25B	0.9800
C8—C9	1.568 (4)	C25—H25C	0.9800
C9—C20	1.537 (4)	Cl1—C26	1.750 (5)
C9—C10	1.563 (4)	Cl2—C26	1.754 (5)
C10—C11	1.539 (4)	Cl3—C26	1.762 (4)
C10—H10	1.0000	C26—H26	1.0000
C6—O2—H1O2	109.5	C12—C13—C14	110.4 (2)
C9—O3—H1O3	109.5	C5—C13—C14	111.5 (2)
C22—O5—C21	113.9 (2)	C12—C13—H13	108.5
C24—O7—C10	116.3 (2)	C5—C13—H13	108.5
O1—C1—C17	122.9 (3)	C14—C13—H13	108.5
O1—C1—C2	119.6 (3)	C15—C14—C13	113.7 (2)
C17—C1—C2	117.5 (2)	C15—C14—H14A	108.8
C3—C2—C1	120.8 (3)	C13—C14—H14A	108.8
C3—C2—H2	119.6	C15—C14—H14B	108.8
C1—C2—H2	119.6	C13—C14—H14B	108.8
C2—C3—C4	124.3 (3)	H14A—C14—H14B	107.7
C2—C3—H3	117.8	C16—C15—C14	110.1 (3)
C4—C3—H3	117.8	C16—C15—H15A	109.6
C3—C4—C16	112.3 (2)	C14—C15—H15A	109.6
C3—C4—C18	106.8 (2)	C16—C15—H15B	109.6
C16—C4—C18	108.7 (3)	C14—C15—H15B	109.6
C3—C4—C5	109.1 (2)	H15A—C15—H15B	108.2
C16—C4—C5	105.8 (2)	C17—C16—C15	122.1 (3)
C18—C4—C5	114.2 (2)	C17—C16—C4	122.4 (3)
F1—C5—C13	106.5 (2)	C15—C16—C4	115.3 (2)
F1—C5—C6	102.8 (2)	C16—C17—C1	122.5 (3)
C13—C5—C6	114.2 (2)	C16—C17—H17	118.8
F1—C5—C4	104.19 (19)	C1—C17—H17	118.8
C13—C5—C4	112.6 (2)	C4—C18—H18A	109.5
C6—C5—C4	115.0 (2)	C4—C18—H18B	109.5
O2—C6—C7	113.3 (2)	H18A—C18—H18B	109.5
O2—C6—C5	106.7 (2)	C4—C18—H18C	109.5
C7—C6—C5	112.3 (2)	H18A—C18—H18C	109.5
O2—C6—H6	108.1	H18B—C18—H18C	109.5
C7—C6—H6	108.1	C8—C19—H19A	109.5
C5—C6—H6	108.1	C8—C19—H19B	109.5
C8—C7—C6	113.8 (2)	H19A—C19—H19B	109.5
C8—C7—H7A	108.8	C8—C19—H19C	109.5
C6—C7—H7A	108.8	H19A—C19—H19C	109.5
C8—C7—H7B	108.8	H19B—C19—H19C	109.5
C6—C7—H7B	108.8	O4—C20—C21	121.8 (2)
H7A—C7—H7B	107.7	O4—C20—C9	122.8 (3)
C7—C8—C12	109.0 (2)	C21—C20—C9	115.4 (2)
C7—C8—C19	110.8 (2)	O5—C21—C20	112.1 (2)
C12—C8—C19	112.3 (2)	O5—C21—H21A	109.2
C7—C8—C9	115.2 (2)	C20—C21—H21A	109.2
C12—C8—C9	98.8 (2)	O5—C21—H21B	109.2
C19—C8—C9	110.2 (2)	C20—C21—H21B	109.2
O3—C9—C20	104.6 (2)	H21A—C21—H21B	107.9
O3—C9—C10	112.4 (2)	O6—C22—O5	121.9 (3)
C20—C9—C10	112.8 (2)	O6—C22—C23	126.3 (3)
O3—C9—C8	111.7 (2)	O5—C22—C23	111.8 (3)
C20—C9—C8	113.1 (2)	C22—C23—H23A	109.5
C10—C9—C8	102.6 (2)	C22—C23—H23B	109.5
O7—C10—C11	106.7 (2)	H23A—C23—H23B	109.5
O7—C10—C9	111.2 (2)	C22—C23—H23C	109.5
C11—C10—C9	106.7 (2)	H23A—C23—H23C	109.5
O7—C10—H10	110.7	H23B—C23—H23C	109.5
C11—C10—H10	110.7	O8—C24—O7	122.5 (3)
C9—C10—H10	110.7	O8—C24—C25	125.2 (3)
C12—C11—C10	103.4 (2)	O7—C24—C25	112.3 (2)
C12—C11—H11A	111.1	C24—C25—H25A	109.5
C10—C11—H11A	111.1	C24—C25—H25B	109.5
C12—C11—H11B	111.1	H25A—C25—H25B	109.5
C10—C11—H11B	111.1	C24—C25—H25C	109.5
H11A—C11—H11B	109.1	H25A—C25—H25C	109.5
C11—C12—C13	120.0 (2)	H25B—C25—H25C	109.5
C11—C12—C8	103.3 (2)	Cl1—C26—Cl2	111.0 (2)
C13—C12—C8	114.4 (2)	Cl1—C26—Cl3	109.7 (2)
C11—C12—H12	106.1	Cl2—C26—Cl3	110.3 (3)
C13—C12—H12	106.1	Cl1—C26—H26	108.6
C8—C12—H12	106.1	Cl2—C26—H26	108.6
C12—C13—C5	109.3 (2)	Cl3—C26—H26	108.6
O1—C1—C2—C3	−178.2 (3)	C10—C11—C12—C8	−38.6 (3)
C17—C1—C2—C3	2.0 (5)	C7—C8—C12—C11	170.8 (2)
C1—C2—C3—C4	0.6 (5)	C19—C8—C12—C11	−66.0 (3)
C2—C3—C4—C16	−3.3 (4)	C9—C8—C12—C11	50.2 (2)
C2—C3—C4—C18	−122.4 (3)	C7—C8—C12—C13	−57.1 (3)
C2—C3—C4—C5	113.7 (3)	C19—C8—C12—C13	66.1 (3)
C3—C4—C5—F1	−63.0 (2)	C9—C8—C12—C13	−177.7 (2)
C16—C4—C5—F1	58.1 (3)	C11—C12—C13—C5	179.2 (2)
C18—C4—C5—F1	177.6 (2)	C8—C12—C13—C5	55.6 (3)
C3—C4—C5—C13	−177.9 (2)	C11—C12—C13—C14	−57.8 (3)
C16—C4—C5—C13	−56.9 (3)	C8—C12—C13—C14	178.6 (2)
C18—C4—C5—C13	62.6 (3)	F1—C5—C13—C12	62.2 (3)
C3—C4—C5—C6	48.8 (3)	C6—C5—C13—C12	−50.5 (3)
C16—C4—C5—C6	169.8 (2)	C4—C5—C13—C12	175.8 (2)
C18—C4—C5—C6	−70.6 (3)	F1—C5—C13—C14	−60.0 (3)
F1—C5—C6—O2	169.3 (2)	C6—C5—C13—C14	−172.8 (2)
C13—C5—C6—O2	−75.8 (3)	C4—C5—C13—C14	53.6 (3)
C4—C5—C6—O2	56.7 (3)	C12—C13—C14—C15	−170.7 (2)
F1—C5—C6—C7	−66.1 (3)	C5—C13—C14—C15	−49.1 (3)
C13—C5—C6—C7	48.9 (3)	C13—C14—C15—C16	49.5 (3)
C4—C5—C6—C7	−178.6 (2)	C14—C15—C16—C17	117.8 (3)
O2—C6—C7—C8	70.7 (3)	C14—C15—C16—C4	−57.4 (3)
C5—C6—C7—C8	−50.3 (3)	C3—C4—C16—C17	3.7 (4)
C6—C7—C8—C12	53.3 (3)	C18—C4—C16—C17	121.7 (3)
C6—C7—C8—C19	−70.7 (3)	C5—C4—C16—C17	−115.2 (3)
C6—C7—C8—C9	163.2 (2)	C3—C4—C16—C15	179.0 (3)
C7—C8—C9—O3	−37.0 (3)	C18—C4—C16—C15	−63.0 (3)
C12—C8—C9—O3	78.9 (2)	C5—C4—C16—C15	60.1 (3)
C19—C8—C9—O3	−163.3 (2)	C15—C16—C17—C1	−176.4 (3)
C7—C8—C9—C20	80.6 (3)	C4—C16—C17—C1	−1.5 (5)
C12—C8—C9—C20	−163.5 (2)	O1—C1—C17—C16	178.7 (3)
C19—C8—C9—C20	−45.7 (3)	C2—C1—C17—C16	−1.6 (5)
C7—C8—C9—C10	−157.6 (2)	O3—C9—C20—O4	−165.7 (3)
C12—C8—C9—C10	−41.7 (2)	C10—C9—C20—O4	−43.3 (4)
C19—C8—C9—C10	76.0 (2)	C8—C9—C20—O4	72.6 (3)
C24—O7—C10—C11	−177.6 (2)	O3—C9—C20—C21	14.5 (3)
C24—O7—C10—C9	66.4 (3)	C10—C9—C20—C21	136.9 (2)
O3—C9—C10—O7	15.1 (3)	C8—C9—C20—C21	−107.2 (3)
C20—C9—C10—O7	−102.8 (2)	C22—O5—C21—C20	−80.2 (3)
C8—C9—C10—O7	135.2 (2)	O4—C20—C21—O5	−17.2 (4)
O3—C9—C10—C11	−100.8 (2)	C9—C20—C21—O5	162.6 (2)
C20—C9—C10—C11	141.3 (2)	C21—O5—C22—O6	4.0 (5)
C8—C9—C10—C11	19.3 (2)	C21—O5—C22—C23	−176.3 (3)
O7—C10—C11—C12	−107.6 (2)	C10—O7—C24—O8	0.6 (4)
C9—C10—C11—C12	11.3 (3)	C10—O7—C24—C25	−178.8 (2)
C10—C11—C12—C13	−167.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O8^i	0.84	1.92	2.750 (3)	169
O3—H1O3···O1^ii	0.84	1.95	2.747 (3)	157

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1/2, −y+3/2, −z+1.