Betamethasone-21-pentanoate methanol solvate

Suitchmezian, V.; Jess, I.; Näther, C.

doi:10.1107/S1600536807059545

Betamethasone-21-pentanoate methanol solvate

In the crystal structure of the title compound {systematic name: 2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl pentanoate methanol solvate}, C₂₇H₃₇FO₆·CH₃OH molecules are connected via O—H

O hydrogen bonding between the hydroxyl H atom and the carbonyl O atom. The molecules are additionally connected via the methanol molecules, which act as hydrogen-bond donors and acceptors.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059545/bt2615sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059545/bt2615Isup2.hkl Contains datablock I

CCDC reference: 673037

checkCIF report

Key indicators

Single-crystal X-ray study
T = 166 K
Mean (C-C) = 0.004 Å
R factor = 0.042
wR factor = 0.114
Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.61 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.20 Ratio

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          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           28.01
           From the CIF: _reflns_number_total               3595
           Count of symmetry unique reflns         3634
           Completeness (_total/calc)             98.93%
           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 C5     ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    ...          S

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

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Glucocorticoids belong to the most effective drugs against inflammatory and auto immune deseases (Auphan, 1995; Besedovsky, 1986; Beato, 1995; Winiski et al., 2007). Surprisingly, their polymorphism is only minor investigated. Therefore, we started systematic investigations on the polymorphism and pseudopolymorphism of these drugs (Suitchmezian et al., 2006a; Suitchmezian et al., 2006b; Suitchmezian et al., 2006c; Näther et al., 2006).

Within this project we also investigated betamethasone valerate, also known as 9-fluoro-11β,21-dihydroxy-16β-methyl-3,20 -dioxypregna-1,4-dien-17-ylpentanoat, (II) (see Fig 3). For this compound we found an methanol solvate, which is still unknown. During our attempts to crystallize this solvate at higher temperatures, we obtained single crystals of the title compound, (I), which formed by a movement of the pentanoat group to position 21. To identify this product in all further investigations by X-ray powder diffraction, the single-crystal structure of this solvate was determined.

In the crystal structure of the title compound, (I), (Fig. 1) the molecules are connected via O—H ··· O hydrogen bonding between the hydroxyl hydrogen atom at O5 and the carbonyl oxygen atom O1 (Tab.1). The molecules are additionally connected by O—H···O hydrogen bonding between the hydroxyl hydrogen atom at O2 and the hydroxyl oxygen atom O7 of the solvent molecules and between the hydroxyl hydrogen atom attached to O7 and the carbonyl oxygen atom O6 (Fig. 2). This, the methanol molecules act as acceptors and donors. In the direction of the a axis channels are formed in which the methanol molecules are located (Fig. 2).

Related literature top

For related literature, see: Auphan (1995); Beato (1995); Besedovsky (1986); Näther & Je\&s (2006); Suitchmezian et al. (2006a,b,c); Winiski et al. (2007).

Experimental top

Betamethasone valerate (9-Fluor-11β,21-dihydroxy-16β-methyl-3,20 -dioxypregna-1,4-dien-17-ylpentanoat) was obtained from Symbiotec Pharmalab (India) as an enantiomeric pure compound. This compound was recrystallized at 70°C in an teflon lined steel autoclave. On cooling, single crystals of the title compound were obtained. The product is obtained as a pure phase, which was proven by comparison of the experimental X-ray powder pattern with that, calculated from single-crystal data.

Computing details top

Data collection: IPDS (Stoe & Cie, 1998); cell refinement: IPDS (Stoe & Cie, 1998); data reduction: IPDS (Stoe & Cie, 1998); 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 (Bruker AXS, 1998).

Figures top

	Fig. 1. View of the asymmetric unit of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal structure of the title compound with view along the a axis (hydrogen bonding is shown as dashed lines).

2-((8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy- 10,13,16-trimethyl-3-oxo- 6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H -cyclopenta[a]phenanthren- 17-yl)-2-oxoethyl pentanoate methanol solvate top

Crystal data top

C₂₇H₃₇FO₆·CH₄O	D_x = 1.261 Mg m⁻³ D_m = N Mg m⁻³ D_m measured by not measured
M_r = 508.61	Melting point: not measured K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.9980 (5) Å	Cell parameters from 16982 reflections
b = 15.7885 (9) Å	θ = 2.4–28.0°
c = 16.9696 (12) Å	µ = 0.09 mm⁻¹
V = 2678.7 (3) Å³	T = 166 K
Z = 4	Needles, colorless
F(000) = 1096	0.15 × 0.10 × 0.04 mm

Data collection top

STOE IPDS-1 diffractometer	3009 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 28.0°, θ_min = 2.4°
Phi scans	h = −13→12
16982 measured reflections	k = −19→20
3595 independent reflections	l = −22→22

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0728P)² + 0.2844P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3595 reflections	Δρ_max = 0.37 e Å⁻³
330 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)

Crystal data top

C₂₇H₃₇FO₆·CH₄O	V = 2678.7 (3) Å³
M_r = 508.61	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.9980 (5) Å	µ = 0.09 mm⁻¹
b = 15.7885 (9) Å	T = 166 K
c = 16.9696 (12) Å	0.15 × 0.10 × 0.04 mm

Data collection top

STOE IPDS-1 diffractometer	3009 reflections with I > 2σ(I)
16982 measured reflections	R_int = 0.049
3595 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	Δρ_max = 0.37 e Å⁻³
3595 reflections	Δρ_min = −0.17 e Å⁻³
330 parameters

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
O1	0.4547 (2)	0.35867 (12)	0.46094 (11)	0.0447 (5)
O2	0.7591 (2)	0.33239 (10)	0.10538 (10)	0.0341 (4)
H1O1	0.7493	0.3492	0.0588	0.051*
O3	0.86752 (19)	0.07486 (12)	−0.10976 (11)	0.0373 (4)
O4	0.6562 (2)	0.11246 (12)	−0.19919 (10)	0.0395 (4)
O5	0.60803 (17)	0.02899 (11)	0.02422 (11)	0.0339 (4)
H1O5	0.6045	−0.0240	0.0281	0.051*
O6	0.6920 (3)	0.23945 (14)	−0.14560 (12)	0.0545 (6)
O7	0.2372 (3)	0.11731 (13)	0.05510 (12)	0.0538 (6)
H1O7	0.2171	0.1575	0.0853	0.081*
F1	0.56997 (13)	0.19207 (9)	0.22638 (8)	0.0293 (3)
C1	0.5279 (3)	0.34132 (15)	0.40401 (14)	0.0321 (5)
C2	0.5175 (3)	0.38628 (15)	0.32881 (14)	0.0299 (5)
H2	0.4524	0.4296	0.3228	0.036*
C3	0.5977 (3)	0.36759 (14)	0.26878 (14)	0.0286 (5)
H3	0.5844	0.3969	0.2205	0.034*
C4	0.7082 (2)	0.30293 (16)	0.27228 (13)	0.0296 (5)
C5	0.6905 (2)	0.23474 (14)	0.20552 (12)	0.0244 (4)
C6	0.6600 (2)	0.27067 (14)	0.12304 (12)	0.0252 (4)
H6	0.5718	0.3003	0.1259	0.030*
C7	0.6487 (2)	0.20086 (14)	0.06002 (13)	0.0247 (4)
H7A	0.5648	0.1689	0.0687	0.030*
H7B	0.6431	0.2277	0.0074	0.030*
C8	0.7664 (2)	0.13873 (13)	0.06056 (12)	0.0233 (4)
C9	0.7443 (2)	0.05480 (14)	0.01248 (13)	0.0264 (5)
C10	0.8411 (3)	−0.01119 (15)	0.05322 (15)	0.0328 (5)
H10	0.7855	−0.0621	0.0656	0.039*
C11	0.8794 (3)	0.02912 (16)	0.13355 (14)	0.0331 (5)
H11A	0.8719	−0.0128	0.1767	0.040*
H11B	0.9719	0.0514	0.1323	0.040*
C12	0.7776 (2)	0.10131 (14)	0.14435 (13)	0.0265 (5)
H12	0.6896	0.0742	0.1565	0.032*
C13	0.8021 (2)	0.16737 (15)	0.20797 (13)	0.0288 (5)
H13	0.8897	0.1957	0.1973	0.035*
C14	0.8090 (3)	0.12488 (18)	0.28931 (14)	0.0397 (6)
H14A	0.8886	0.0876	0.2912	0.048*
H14B	0.7288	0.0889	0.2965	0.048*
C15	0.8168 (3)	0.1888 (2)	0.35744 (15)	0.0459 (7)
H15A	0.8055	0.1585	0.4081	0.055*
H15B	0.9062	0.2158	0.3576	0.055*
C16	0.7115 (3)	0.25614 (17)	0.35066 (14)	0.0331 (5)
C17	0.6280 (3)	0.27433 (17)	0.40949 (14)	0.0347 (6)
H17	0.6339	0.2424	0.4568	0.042*
C18	0.8407 (3)	0.35432 (19)	0.26525 (16)	0.0401 (6)
H18A	0.9170	0.3155	0.2676	0.060*
H18B	0.8464	0.3950	0.3087	0.060*
H18C	0.8419	0.3848	0.2150	0.060*
C19	0.8963 (2)	0.18166 (14)	0.03324 (13)	0.0267 (4)
H19A	0.9695	0.1404	0.0341	0.040*
H19B	0.9176	0.2288	0.0687	0.040*
H19C	0.8847	0.2032	−0.0205	0.040*
C20	0.9629 (3)	−0.04336 (18)	0.00755 (17)	0.0410 (6)
H20A	0.9336	−0.0683	−0.0424	0.062*
H20B	1.0095	−0.0863	0.0389	0.062*
H20C	1.0237	0.0040	−0.0031	0.062*
C21	0.7607 (3)	0.06993 (14)	−0.07560 (13)	0.0293 (5)
C22	0.6305 (3)	0.08233 (18)	−0.12067 (15)	0.0359 (6)
H22A	0.5816	0.0279	−0.1233	0.043*
H22B	0.5735	0.1236	−0.0924	0.043*
C23	0.6882 (3)	0.19431 (19)	−0.20325 (16)	0.0395 (6)
C24	0.7145 (3)	0.2230 (2)	−0.28574 (17)	0.0492 (8)
H24A	0.6439	0.1999	−0.3206	0.059*
H24B	0.8012	0.1994	−0.3034	0.059*
C25	0.7181 (3)	0.3179 (2)	−0.29465 (18)	0.0492 (7)
H25A	0.6345	0.3417	−0.2726	0.059*
H25B	0.7935	0.3403	−0.2631	0.059*
C26	0.7331 (5)	0.3483 (2)	−0.37817 (19)	0.0616 (9)
H26A	0.8181	0.3262	−0.3999	0.074*
H26B	0.6591	0.3249	−0.4103	0.074*
C27	0.7325 (6)	0.4429 (3)	−0.3852 (3)	0.0842 (14)
H27A	0.7415	0.4589	−0.4408	0.126*
H27B	0.8075	0.4664	−0.3551	0.126*
H27C	0.6482	0.4652	−0.3644	0.126*
C28	0.3002 (3)	0.0530 (2)	0.09857 (19)	0.0468 (7)
H28A	0.3839	0.0746	0.1209	0.070*
H28B	0.3195	0.0049	0.0639	0.070*
H28C	0.2410	0.0345	0.1413	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0559 (13)	0.0369 (9)	0.0414 (10)	0.0089 (9)	0.0246 (9)	0.0001 (8)
O2	0.0466 (11)	0.0262 (8)	0.0294 (8)	−0.0058 (8)	0.0022 (8)	0.0026 (6)
O3	0.0330 (10)	0.0468 (11)	0.0322 (9)	0.0017 (8)	0.0091 (7)	−0.0023 (8)
O4	0.0453 (11)	0.0422 (10)	0.0309 (9)	0.0044 (9)	−0.0036 (8)	−0.0048 (8)
O5	0.0265 (9)	0.0286 (8)	0.0467 (10)	−0.0063 (7)	0.0078 (7)	−0.0001 (8)
O6	0.0805 (17)	0.0417 (11)	0.0412 (11)	−0.0009 (11)	0.0090 (11)	−0.0043 (9)
O7	0.0847 (17)	0.0376 (10)	0.0392 (10)	0.0193 (11)	−0.0032 (11)	0.0084 (8)
F1	0.0257 (7)	0.0326 (7)	0.0295 (7)	0.0000 (6)	0.0054 (5)	0.0035 (5)
C1	0.0343 (13)	0.0287 (11)	0.0333 (12)	0.0015 (10)	0.0064 (10)	−0.0052 (9)
C2	0.0299 (13)	0.0234 (10)	0.0366 (12)	0.0041 (9)	0.0015 (10)	−0.0032 (9)
C3	0.0311 (12)	0.0261 (10)	0.0284 (11)	−0.0004 (9)	−0.0020 (9)	−0.0015 (9)
C4	0.0273 (12)	0.0370 (12)	0.0245 (10)	0.0042 (10)	0.0009 (8)	−0.0014 (9)
C5	0.0221 (11)	0.0283 (10)	0.0228 (9)	0.0003 (9)	0.0029 (8)	0.0023 (8)
C6	0.0254 (11)	0.0259 (10)	0.0243 (10)	0.0048 (9)	0.0002 (8)	0.0023 (8)
C7	0.0240 (11)	0.0271 (10)	0.0230 (9)	0.0030 (9)	−0.0003 (8)	0.0023 (8)
C8	0.0221 (11)	0.0241 (9)	0.0237 (9)	0.0023 (8)	0.0027 (8)	0.0023 (8)
C9	0.0233 (11)	0.0246 (10)	0.0314 (11)	−0.0010 (9)	0.0057 (9)	0.0001 (8)
C10	0.0320 (13)	0.0263 (11)	0.0402 (13)	0.0047 (10)	0.0076 (10)	0.0027 (9)
C11	0.0348 (14)	0.0309 (11)	0.0336 (12)	0.0128 (10)	0.0039 (10)	0.0059 (9)
C12	0.0269 (12)	0.0263 (10)	0.0263 (10)	0.0058 (9)	0.0042 (9)	0.0048 (8)
C13	0.0268 (12)	0.0354 (12)	0.0243 (10)	0.0094 (9)	0.0004 (9)	0.0033 (9)
C14	0.0453 (16)	0.0471 (15)	0.0267 (11)	0.0214 (13)	−0.0002 (11)	0.0070 (10)
C15	0.0485 (17)	0.0626 (18)	0.0266 (11)	0.0278 (15)	−0.0038 (11)	0.0038 (12)
C16	0.0343 (14)	0.0396 (13)	0.0255 (11)	0.0092 (11)	−0.0037 (9)	−0.0015 (10)
C17	0.0448 (15)	0.0361 (13)	0.0233 (10)	0.0066 (11)	0.0021 (10)	−0.0013 (9)
C18	0.0303 (14)	0.0520 (16)	0.0381 (13)	−0.0047 (12)	−0.0011 (11)	−0.0109 (12)
C19	0.0248 (11)	0.0281 (11)	0.0272 (10)	−0.0024 (9)	0.0022 (8)	0.0015 (9)
C20	0.0403 (15)	0.0383 (14)	0.0444 (14)	0.0138 (12)	0.0049 (12)	−0.0032 (11)
C21	0.0321 (13)	0.0254 (10)	0.0306 (11)	−0.0016 (9)	0.0042 (9)	−0.0048 (8)
C22	0.0342 (14)	0.0407 (13)	0.0328 (12)	0.0001 (11)	0.0010 (10)	−0.0056 (10)
C23	0.0354 (14)	0.0465 (15)	0.0365 (13)	0.0094 (12)	0.0024 (11)	−0.0023 (11)
C24	0.0498 (19)	0.0592 (18)	0.0386 (14)	0.0138 (15)	0.0078 (13)	0.0033 (13)
C25	0.0459 (18)	0.0598 (18)	0.0419 (15)	−0.0004 (15)	0.0050 (13)	−0.0012 (13)
C26	0.069 (2)	0.071 (2)	0.0439 (16)	0.002 (2)	0.0097 (17)	0.0088 (15)
C27	0.093 (3)	0.070 (2)	0.089 (3)	0.008 (3)	0.026 (3)	0.034 (2)
C28	0.0436 (17)	0.0467 (15)	0.0502 (16)	0.0134 (13)	0.0040 (13)	0.0122 (13)

Geometric parameters (Å, º) top

O1—C1	1.243 (3)	C12—H12	1.0000
O2—C6	1.421 (3)	C13—C14	1.536 (3)
O2—H1O1	0.8400	C13—H13	1.0000
O3—C21	1.217 (3)	C14—C15	1.537 (4)
O4—C23	1.333 (4)	C14—H14A	0.9900
O4—C22	1.438 (3)	C14—H14B	0.9900
O5—C9	1.436 (3)	C15—C16	1.499 (4)
O5—H1O5	0.8400	C15—H15A	0.9900
O6—C23	1.211 (3)	C15—H15B	0.9900
O7—C28	1.404 (3)	C16—C17	1.333 (3)
O7—H1O7	0.8400	C17—H17	0.9500
F1—C5	1.426 (3)	C18—H18A	0.9800
C1—C17	1.459 (4)	C18—H18B	0.9800
C1—C2	1.464 (3)	C18—H18C	0.9800
C2—C3	1.329 (3)	C19—H19A	0.9800
C2—H2	0.9500	C19—H19B	0.9800
C3—C4	1.505 (3)	C19—H19C	0.9800
C3—H3	0.9500	C20—H20A	0.9800
C4—C16	1.522 (3)	C20—H20B	0.9800
C4—C18	1.558 (4)	C20—H20C	0.9800
C4—C5	1.573 (3)	C21—C22	1.523 (4)
C5—C6	1.541 (3)	C22—H22A	0.9900
C5—C13	1.542 (3)	C22—H22B	0.9900
C6—C7	1.540 (3)	C23—C24	1.495 (4)
C6—H6	1.0000	C24—C25	1.506 (5)
C7—C8	1.532 (3)	C24—H24A	0.9900
C7—H7A	0.9900	C24—H24B	0.9900
C7—H7B	0.9900	C25—C26	1.504 (4)
C8—C19	1.537 (3)	C25—H25A	0.9900
C8—C12	1.544 (3)	C25—H25B	0.9900
C8—C9	1.572 (3)	C26—C27	1.498 (6)
C9—C21	1.523 (3)	C26—H26A	0.9900
C9—C10	1.581 (3)	C26—H26B	0.9900
C10—C20	1.531 (4)	C27—H27A	0.9800
C10—C11	1.552 (4)	C27—H27B	0.9800
C10—H10	1.0000	C27—H27C	0.9800
C11—C12	1.539 (3)	C28—H28A	0.9800
C11—H11A	0.9900	C28—H28B	0.9800
C11—H11B	0.9900	C28—H28C	0.9800
C12—C13	1.521 (3)

C6—O2—H1O1	109.5	C13—C14—H14B	109.0
C23—O4—C22	114.3 (2)	C15—C14—H14B	109.0
C9—O5—H1O5	109.5	H14A—C14—H14B	107.8
C28—O7—H1O7	109.5	C16—C15—C14	111.9 (2)
O1—C1—C17	120.9 (2)	C16—C15—H15A	109.2
O1—C1—C2	121.9 (2)	C14—C15—H15A	109.2
C17—C1—C2	117.1 (2)	C16—C15—H15B	109.2
C3—C2—C1	121.2 (2)	C14—C15—H15B	109.2
C3—C2—H2	119.4	H15A—C15—H15B	107.9
C1—C2—H2	119.4	C17—C16—C15	122.3 (2)
C2—C3—C4	124.3 (2)	C17—C16—C4	122.4 (2)
C2—C3—H3	117.9	C15—C16—C4	115.2 (2)
C4—C3—H3	117.9	C16—C17—C1	122.6 (2)
C3—C4—C16	112.32 (19)	C16—C17—H17	118.7
C3—C4—C18	105.5 (2)	C1—C17—H17	118.7
C16—C4—C18	107.5 (2)	C4—C18—H18A	109.5
C3—C4—C5	110.70 (19)	C4—C18—H18B	109.5
C16—C4—C5	107.44 (19)	H18A—C18—H18B	109.5
C18—C4—C5	113.38 (19)	C4—C18—H18C	109.5
F1—C5—C6	103.42 (17)	H18A—C18—H18C	109.5
F1—C5—C13	106.20 (17)	H18B—C18—H18C	109.5
C6—C5—C13	114.95 (18)	C8—C19—H19A	109.5
F1—C5—C4	103.86 (16)	C8—C19—H19B	109.5
C6—C5—C4	115.12 (18)	H19A—C19—H19B	109.5
C13—C5—C4	111.82 (18)	C8—C19—H19C	109.5
O2—C6—C7	113.29 (18)	H19A—C19—H19C	109.5
O2—C6—C5	107.81 (18)	H19B—C19—H19C	109.5
C7—C6—C5	112.45 (18)	C10—C20—H20A	109.5
O2—C6—H6	107.7	C10—C20—H20B	109.5
C7—C6—H6	107.7	H20A—C20—H20B	109.5
C5—C6—H6	107.7	C10—C20—H20C	109.5
C8—C7—C6	113.44 (18)	H20A—C20—H20C	109.5
C8—C7—H7A	108.9	H20B—C20—H20C	109.5
C6—C7—H7A	108.9	O3—C21—C9	124.9 (2)
C8—C7—H7B	108.9	O3—C21—C22	120.2 (2)
C6—C7—H7B	108.9	C9—C21—C22	114.9 (2)
H7A—C7—H7B	107.7	O4—C22—C21	110.8 (2)
C7—C8—C19	111.41 (17)	O4—C22—H22A	109.5
C7—C8—C12	107.84 (17)	C21—C22—H22A	109.5
C19—C8—C12	112.66 (18)	O4—C22—H22B	109.5
C7—C8—C9	115.37 (19)	C21—C22—H22B	109.5
C19—C8—C9	109.53 (17)	H22A—C22—H22B	108.1
C12—C8—C9	99.53 (16)	O6—C23—O4	122.4 (3)
O5—C9—C21	106.5 (2)	O6—C23—C24	124.9 (3)
O5—C9—C8	107.51 (18)	O4—C23—C24	112.6 (2)
C21—C9—C8	111.22 (17)	C23—C24—C25	113.6 (3)
O5—C9—C10	109.46 (18)	C23—C24—H24A	108.9
C21—C9—C10	117.8 (2)	C25—C24—H24A	108.9
C8—C9—C10	104.02 (19)	C23—C24—H24B	108.9
C20—C10—C11	112.6 (2)	C25—C24—H24B	108.9
C20—C10—C9	119.0 (2)	H24A—C24—H24B	107.7
C11—C10—C9	105.36 (18)	C26—C25—C24	114.5 (3)
C20—C10—H10	106.4	C26—C25—H25A	108.6
C11—C10—H10	106.4	C24—C25—H25A	108.6
C9—C10—H10	106.4	C26—C25—H25B	108.6
C12—C11—C10	104.20 (19)	C24—C25—H25B	108.6
C12—C11—H11A	110.9	H25A—C25—H25B	107.6
C10—C11—H11A	110.9	C27—C26—C25	113.1 (3)
C12—C11—H11B	110.9	C27—C26—H26A	109.0
C10—C11—H11B	110.9	C25—C26—H26A	109.0
H11A—C11—H11B	108.9	C27—C26—H26B	109.0
C13—C12—C11	119.1 (2)	C25—C26—H26B	109.0
C13—C12—C8	113.76 (18)	H26A—C26—H26B	107.8
C11—C12—C8	102.81 (17)	C26—C27—H27A	109.5
C13—C12—H12	106.8	C26—C27—H27B	109.5
C11—C12—H12	106.8	H27A—C27—H27B	109.5
C8—C12—H12	106.8	C26—C27—H27C	109.5
C12—C13—C14	110.2 (2)	H27A—C27—H27C	109.5
C12—C13—C5	109.73 (19)	H27B—C27—H27C	109.5
C14—C13—C5	110.97 (19)	O7—C28—H28A	109.5
C12—C13—H13	108.6	O7—C28—H28B	109.5
C14—C13—H13	108.6	H28A—C28—H28B	109.5
C5—C13—H13	108.6	O7—C28—H28C	109.5
C13—C14—C15	113.0 (2)	H28A—C28—H28C	109.5
C13—C14—H14A	109.0	H28B—C28—H28C	109.5
C15—C14—H14A	109.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O1···O7ⁱ	0.84	2.01	2.845 (3)	176
O5—H1O5···O1ⁱⁱ	0.84	1.95	2.773 (2)	165
O7—H1O7···O6ⁱⁱⁱ	0.84	1.94	2.771 (3)	171

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

Experimental details

Crystal data
Chemical formula	C₂₇H₃₇FO₆·CH₄O
M_r	508.61
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	166
a, b, c (Å)	9.9980 (5), 15.7885 (9), 16.9696 (12)
V (Å³)	2678.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.15 × 0.10 × 0.04

Data collection
Diffractometer	STOE IPDS1 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16982, 3595, 3009
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.114, 1.03
No. of reflections	3595
No. of parameters	330
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.17

Computer programs: IPDS (Stoe & Cie, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1998), CIFTAB in SHELXTL (Bruker AXS, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O1···O7ⁱ	0.84	2.01	2.845 (3)	175.5
O5—H1O5···O1ⁱⁱ	0.84	1.95	2.773 (2)	164.7
O7—H1O7···O6ⁱⁱⁱ	0.84	1.94	2.771 (3)	170.8

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

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