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The an­hydro­us crystal structure of the title compound, 9α-chloro-16β-methyl-3,20-dioxo-1,4-pregna­diene-11β,17,21-triol 17,21-dipropionate, C28H37ClO7, was determined by single-crystal X-ray diffractometry using direct methods. Beclomethasone dipropionate, BDP, is an important pharmaceutical steroid for the treatment of asthma. It is formulated for inhalation delivery either as a solution or as a suspension of crystals in liquefied halogenated-alkanes. The physico-chemical properties of the crystals in suspension are of critical importance. Density will affect suspendability and settling rate, and different crystal forms may have significantly different dissolution rates in vivo. Until now, only the monohydrate form of BDP has been published [Duax et al. (1981). Acta Cryst. B37, 383–387]. This study presents the structure of the an­hydro­us form of BDP. The an­hydro­us form is intermolecularly hydrogen bonded and its efficient packing results in a more dense crystal (1.362 Mg m−3) than the published monohydrate form (1.287 Mg m−3).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009406/om6090sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009406/om6090Isup2.hkl
Contains datablock I

CCDC reference: 189884

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.072
  • Data-to-parameter ratio = 14.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.66 From the CIF: _reflns_number_total 4799 Count of symmetry unique reflns 2715 Completeness (_total/calc) 176.76% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2084 Fraction of Friedel pairs measured 0.768 Are heavy atom types Z>Si present yes 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.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL/PC (Bruker, 1997); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

9α-chloro-16β-methyl-3,20-dioxo-1,4-pregnadiene-11β,17,21-triol 17,21-dipropionate top
Crystal data top
C28H37ClO7Dx = 1.362 Mg m3
Mr = 521.03Melting point: 486.70 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5087 reflections
a = 12.1239 (15) Åθ = 5.7–51.3°
b = 14.1289 (17) ŵ = 0.20 mm1
c = 14.8381 (18) ÅT = 100 K
V = 2541.7 (5) Å3Irregular block, colorless
Z = 40.40 × 0.30 × 0.25 mm
F(000) = 1112
Data collection top
Bruker CCD area-detector
diffractometer
4799 independent reflections
Radiation source: fine-focus sealed tube4507 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 8.192 pixels mm-1θmax = 25.7°, θmin = 2.0°
ω scansh = 1414
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1717
Tmin = 0.923, Tmax = 0.952l = 1818
25323 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.0386P)2 + 0.3771P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
4799 reflectionsΔρmax = 0.25 e Å3
331 parametersΔρmin = 0.15 e Å3
0 restraintsAbsolute structure: (Flack, 1983), 2086 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (4)
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
xyzUiso*/Ueq
Cl10.15059 (3)0.33651 (3)0.93011 (3)0.01699 (10)
C10.05521 (14)0.38287 (12)0.80701 (12)0.0168 (4)
C20.09520 (14)0.29623 (12)0.79205 (12)0.0176 (4)
C30.12659 (14)0.23459 (12)0.86672 (12)0.0176 (4)
C40.12420 (14)0.27555 (12)0.95735 (12)0.0180 (4)
C50.08493 (14)0.36275 (12)0.97369 (12)0.0180 (4)
C60.07631 (15)0.40361 (13)1.06706 (12)0.0207 (4)
C70.03977 (15)0.44053 (12)1.08833 (11)0.0185 (4)
C80.08850 (13)0.50151 (12)1.01263 (11)0.0149 (3)
C90.07953 (14)0.45151 (11)0.92098 (12)0.0149 (3)
C100.04490 (14)0.42699 (11)0.89877 (11)0.0157 (4)
C110.14463 (14)0.49978 (11)0.84280 (11)0.0152 (3)
C120.26046 (14)0.53354 (12)0.87083 (12)0.0154 (4)
C130.25939 (13)0.59114 (11)0.95880 (11)0.0149 (3)
C140.20708 (14)0.52942 (11)1.03312 (12)0.0152 (3)
C150.22708 (14)0.58732 (12)1.11812 (12)0.0177 (4)
C160.34446 (16)0.62867 (11)1.10645 (12)0.0181 (4)
C170.37384 (14)0.61333 (11)1.00403 (12)0.0158 (4)
C180.19869 (14)0.68661 (11)0.94580 (12)0.0173 (4)
C190.12088 (15)0.51637 (12)0.89719 (12)0.0200 (4)
C200.43572 (14)0.69070 (12)0.95290 (12)0.0176 (4)
C210.51340 (15)0.65787 (13)0.87765 (12)0.0216 (4)
C220.45698 (15)0.76157 (13)0.76372 (12)0.0222 (4)
C230.48661 (17)0.84763 (15)0.70912 (14)0.0322 (5)
C240.3901 (2)0.91434 (16)0.70450 (18)0.0476 (7)
C250.53772 (14)0.52588 (11)1.03982 (12)0.0180 (4)
C260.59007 (14)0.42939 (12)1.04460 (12)0.0199 (4)
C270.63507 (16)0.41014 (13)1.13868 (12)0.0235 (4)
C280.35578 (16)0.72816 (12)1.14641 (12)0.0217 (4)
H10.03180.41890.75640.02*
H20.10340.27440.73190.021*
H40.15140.23911.00640.022*
H6A0.09630.35431.11150.025*
H6B0.12980.45621.07320.025*
H7A0.08920.3861.09930.022*
H7B0.03690.47851.14440.022*
H80.0440.5611.00910.018*
H110.15410.45170.79390.018*
H11A0.11370.59210.76570.036 (7)*
H12A0.3090.47780.87870.018*
H12B0.29180.5730.8220.018*
H140.25150.471.0380.018*
H15A0.22310.54671.17240.021*
H15B0.17190.63861.12370.021*
H160.39520.58691.14170.022*
H18A0.22880.71930.8930.026*
H18B0.20910.72610.99940.026*
H18C0.11980.67490.93670.026*
H19A0.09930.55750.8470.03*
H19B0.11320.55090.95410.03*
H19C0.19780.49670.88950.03*
H21A0.5820.63230.90450.026*
H21B0.47770.60650.84290.026*
H23A0.55040.88010.73710.039*
H23B0.5080.82820.64750.039*
H24A0.32730.88220.67640.071*
H24B0.41020.96990.66860.071*
H24C0.36990.93440.76550.071*
H26A0.65080.42541.00020.024*
H26B0.53470.38061.0290.024*
H27A0.68420.46191.15660.035*
H27B0.67620.35041.13850.035*
H27C0.57370.40571.18150.035*
H28A0.30350.77091.11670.033*
H28B0.43110.75121.1370.033*
H28C0.33990.7261.21110.033*
O30.15232 (11)0.15042 (8)0.85435 (8)0.0222 (3)
O110.07910 (10)0.57439 (8)0.80748 (8)0.0192 (3)
O170.43926 (9)0.52555 (8)0.99752 (8)0.0162 (3)
O200.42063 (10)0.77456 (8)0.96527 (8)0.0211 (3)
O210.54011 (10)0.73429 (9)0.81850 (9)0.0229 (3)
O220.37005 (11)0.72110 (9)0.76001 (9)0.0287 (3)
O250.57913 (10)0.59710 (8)1.07041 (9)0.0234 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0193 (2)0.01071 (17)0.0210 (2)0.00139 (15)0.00019 (17)0.00014 (16)
C10.0153 (8)0.0175 (9)0.0175 (9)0.0007 (7)0.0014 (7)0.0008 (7)
C20.0167 (9)0.0186 (9)0.0176 (9)0.0001 (7)0.0007 (7)0.0038 (7)
C30.0147 (8)0.0146 (8)0.0236 (9)0.0001 (7)0.0004 (7)0.0013 (7)
C40.0175 (8)0.0158 (8)0.0208 (9)0.0022 (7)0.0035 (7)0.0020 (7)
C50.0139 (8)0.0182 (8)0.0218 (9)0.0002 (7)0.0021 (7)0.0022 (7)
C60.0230 (9)0.0192 (8)0.0200 (9)0.0032 (7)0.0059 (8)0.0009 (8)
C70.0233 (9)0.0188 (8)0.0133 (9)0.0020 (7)0.0010 (7)0.0009 (7)
C80.0162 (8)0.0117 (8)0.0169 (9)0.0007 (7)0.0000 (7)0.0002 (7)
C90.0165 (8)0.0087 (7)0.0194 (9)0.0013 (6)0.0014 (7)0.0001 (7)
C100.0172 (9)0.0117 (8)0.0183 (9)0.0006 (7)0.0000 (7)0.0010 (7)
C110.0181 (8)0.0128 (7)0.0147 (8)0.0006 (7)0.0008 (7)0.0007 (6)
C120.0170 (9)0.0128 (8)0.0164 (9)0.0005 (6)0.0004 (7)0.0012 (7)
C130.0160 (8)0.0123 (8)0.0164 (9)0.0009 (7)0.0013 (7)0.0009 (7)
C140.0174 (8)0.0109 (8)0.0172 (9)0.0017 (6)0.0003 (7)0.0009 (7)
C150.0204 (9)0.0161 (9)0.0168 (9)0.0002 (7)0.0008 (7)0.0013 (7)
C160.0200 (9)0.0144 (8)0.0199 (9)0.0009 (7)0.0022 (7)0.0004 (7)
C170.0185 (9)0.0087 (8)0.0203 (9)0.0020 (6)0.0012 (7)0.0011 (6)
C180.0190 (9)0.0130 (8)0.0199 (9)0.0003 (6)0.0029 (7)0.0002 (7)
C190.0192 (9)0.0154 (8)0.0255 (10)0.0009 (7)0.0008 (7)0.0019 (7)
C200.0145 (8)0.0172 (8)0.0213 (9)0.0014 (6)0.0070 (7)0.0005 (7)
C210.0229 (9)0.0163 (8)0.0257 (10)0.0020 (7)0.0002 (8)0.0030 (8)
C220.0267 (10)0.0207 (9)0.0191 (9)0.0042 (8)0.0023 (8)0.0019 (8)
C230.0375 (12)0.0316 (11)0.0276 (11)0.0128 (9)0.0015 (9)0.0057 (9)
C240.0445 (14)0.0301 (12)0.0682 (17)0.0098 (11)0.0144 (12)0.0223 (12)
C250.0183 (8)0.0169 (9)0.0188 (9)0.0001 (7)0.0015 (7)0.0024 (7)
C260.0189 (9)0.0158 (8)0.0250 (10)0.0023 (7)0.0016 (7)0.0025 (7)
C270.0230 (9)0.0192 (9)0.0282 (10)0.0021 (8)0.0002 (8)0.0022 (8)
C280.0258 (9)0.0182 (8)0.0212 (9)0.0036 (8)0.0021 (8)0.0042 (7)
O30.0277 (7)0.0125 (6)0.0263 (7)0.0027 (5)0.0013 (6)0.0027 (5)
O110.0202 (6)0.0171 (6)0.0203 (7)0.0010 (5)0.0019 (5)0.0045 (5)
O170.0169 (6)0.0108 (6)0.0209 (6)0.0013 (5)0.0020 (5)0.0013 (5)
O200.0256 (7)0.0118 (6)0.0259 (7)0.0029 (5)0.0028 (5)0.0003 (5)
O210.0233 (7)0.0212 (6)0.0242 (7)0.0068 (5)0.0014 (5)0.0048 (6)
O220.0287 (8)0.0275 (7)0.0299 (7)0.0087 (6)0.0036 (6)0.0059 (6)
O250.0216 (6)0.0155 (6)0.0330 (7)0.0023 (5)0.0064 (6)0.0015 (6)
Geometric parameters (Å, º) top
Cl1—C91.8440 (16)C16—H161
C1—C101.503 (2)C17—C161.576 (2)
C1—C21.335 (2)C17—C201.528 (2)
C1—H10.95C17—O171.4752 (19)
C2—H20.95C18—H18A0.98
C3—C21.460 (2)C18—H18B0.98
C3—C41.464 (2)C18—H18C0.98
C3—O31.243 (2)C19—C101.563 (2)
C4—H40.95C19—H19A0.98
C5—C101.515 (2)C19—H19B0.98
C5—C41.343 (2)C19—H19C0.98
C5—C61.504 (3)C21—C201.533 (2)
C6—H6A0.99C21—H21A0.99
C6—H6B0.99C21—H21B0.99
C7—C61.534 (2)C21—O211.429 (2)
C7—C81.534 (2)C22—C231.505 (3)
C7—H7A0.99C23—C241.504 (3)
C7—H7B0.99C23—H23A0.99
C8—C141.521 (2)C23—H23B0.99
C8—H81C24—H24A0.98
C9—C101.583 (2)C24—H24B0.98
C9—C111.560 (2)C24—H24C0.98
C9—C81.536 (2)C25—C261.505 (2)
C11—H111C26—C271.523 (3)
C11—O111.420 (2)C26—H26A0.99
C12—C111.540 (2)C26—H26B0.99
C12—H12A0.99C27—H27A0.98
C12—H12B0.99C27—H27B0.98
C13—C121.538 (2)C27—H27C0.98
C13—C141.542 (2)C28—H28A0.98
C13—C171.573 (2)C28—H28B0.98
C13—C181.549 (2)C28—H28C0.98
C14—H141O17—C251.349 (2)
C15—C141.523 (2)O20—C201.213 (2)
C15—C161.548 (3)O21—C221.351 (2)
C15—H15A0.99O22—C221.200 (2)
C15—H15B0.99O25—C251.213 (2)
C16—C281.532 (2)
C1—C10—C19105.81 (14)C16—C28—H28A109.5
C1—C10—C5112.93 (14)C16—C28—H28B109.5
C1—C10—C9111.03 (14)C16—C28—H28C109.5
C1—C2—C3121.02 (16)C17—C16—H16106.5
C1—C2—H2119.5C17—C20—C21116.56 (14)
C2—C1—C10124.14 (16)C18—C13—C17107.39 (13)
C2—C1—H1117.9C19—C10—C9112.83 (13)
C2—C3—C4117.14 (14)C20—C17—C13111.34 (14)
C3—C2—H2119.5C20—C17—C16119.45 (14)
C3—C4—H4118.8C20—C21—H21A109.4
C4—C5—C10122.06 (16)C20—C21—H21B109.4
C4—C5—C6122.89 (16)C22—C23—H23A109.6
C5—C10—C19107.83 (14)C22—C23—H23B109.6
C5—C10—C9106.48 (14)C22—O21—C21114.59 (13)
C5—C4—C3122.37 (16)C23—C24—H24A109.5
C5—C4—H4118.8C23—C24—H24B109.5
C5—C6—C7112.57 (14)C23—C24—H24C109.5
C5—C6—H6A109.1C24—C23—C22110.20 (17)
C5—C6—H6B109.1C24—C23—H23A109.6
C6—C5—C10115.06 (14)C24—C23—H23B109.6
C6—C7—C8113.19 (14)C25—C26—C27110.85 (15)
C6—C7—H7A108.9C25—C26—H26A109.5
C6—C7—H7B108.9C25—C26—H26B109.5
C7—C6—H6A109.1C25—O17—C17116.26 (12)
C7—C6—H6B109.1C26—C27—H27A109.5
C7—C8—C9111.26 (13)C26—C27—H27B109.5
C7—C8—H8107.6C26—C27—H27C109.5
C8—C14—C13113.09 (14)C27—C26—H26A109.5
C8—C14—C15117.08 (14)C27—C26—H26B109.5
C8—C14—H14107.8C28—C16—C15112.67 (15)
C8—C7—H7A108.9C28—C16—C17118.63 (14)
C8—C7—H7B108.9C28—C16—H16106.5
C8—C9—C10110.64 (13)H6A—C6—H6B107.8
C8—C9—C11114.92 (13)H7A—C7—H7B107.8
C8—C9—Cl1107.89 (11)H12A—C12—H12B107.8
C9—C11—H11107.5H15A—C15—H15B108.8
C9—C8—H8107.6H18A—C18—H18B109.5
C10—C1—H1117.9H18A—C18—H18C109.5
C10—C19—H19A109.5H18B—C18—H18C109.5
C10—C19—H19B109.5H19A—C19—H19B109.5
C10—C19—H19C109.5H19A—C19—H19C109.5
C10—C9—Cl1105.53 (11)H19B—C19—H19C109.5
C11—C12—H12A109.1H21A—C21—H21B108
C11—C12—H12B109.1H23A—C23—H23B108.1
C11—C9—C10115.03 (14)H24A—C24—H24B109.5
C11—C9—Cl1101.74 (11)H24A—C24—H24C109.5
C12—C11—C9113.31 (13)H24B—C24—H24C109.5
C12—C11—H11107.5H26A—C26—H26B108.1
C12—C13—C14108.12 (13)H27A—C27—H27B109.5
C12—C13—C17117.39 (13)H27A—C27—H27C109.5
C12—C13—C18111.05 (13)H27B—C27—H27C109.5
C13—C12—C11112.66 (13)H28A—C28—H28B109.5
C13—C12—H12A109.1H28A—C28—H28C109.5
C13—C12—H12B109.1H28B—C28—H28C109.5
C13—C14—H14107.8O3—C3—C2121.61 (16)
C13—C17—C16103.85 (14)O3—C3—C4121.24 (15)
C13—C18—H18A109.5O11—C11—C12112.32 (13)
C13—C18—H18B109.5O11—C11—C9108.42 (13)
C13—C18—H18C109.5O11—C11—H11107.5
C14—C13—C1799.80 (13)O17—C17—C13106.19 (12)
C14—C13—C18112.71 (14)O17—C17—C16107.48 (13)
C14—C15—C16104.86 (14)O17—C17—C20107.76 (13)
C14—C15—H15A110.8O17—C25—C26113.08 (14)
C14—C15—H15B110.8O20—C20—C17123.35 (16)
C14—C8—C7111.29 (14)O20—C20—C21119.91 (16)
C14—C8—C9111.29 (13)O21—C21—C20110.99 (14)
C14—C8—H8107.6O21—C21—H21A109.4
C15—C14—C13102.88 (13)O21—C21—H21B109.4
C15—C14—H14107.8O21—C22—C23112.11 (15)
C15—C16—C17105.29 (14)O22—C22—C23124.74 (17)
C15—C16—H16106.5O22—C22—O21123.15 (16)
C16—C15—H15A110.8O25—C25—C26124.00 (16)
C16—C15—H15B110.8O25—C25—O17122.92 (15)
Cl1—C9—C10—C166.66 (15)C12—C13—C17—C16155.24 (13)
Cl1—C9—C10—C556.64 (14)C13—C12—C11—O1174.33 (17)
Cl1—C9—C10—C19174.74 (12)C13—C12—C11—C948.96 (18)
Cl1—C9—C11—O11160.97 (10)C13—C17—C16—C28111.50 (17)
Cl1—C9—C11—C1273.63 (14)C13—C17—C16—C1515.70 (16)
Cl1—C9—C8—C1467.51 (15)C13—C17—C20—O2084.6 (2)
Cl1—C9—C8—C757.23 (16)C13—C17—C20—C2190.57 (17)
C2—C1—C10—C50.0 (2)C13—C17—O17—C25174.13 (13)
C2—C1—C10—C19117.78 (18)C14—C13—C12—C1157.07 (17)
C2—C1—C10—C9119.47 (18)C14—C13—C17—O1774.37 (14)
C2—C3—C4—C56.4 (2)C14—C13—C17—C20168.60 (13)
C4—C3—C2—C16.8 (2)C14—C13—C17—C1638.81 (15)
C4—C5—C10—C10.5 (2)C14—C15—C16—C28144.82 (14)
C4—C5—C10—C19117.05 (17)C14—C15—C16—C1714.08 (17)
C4—C5—C10—C9121.60 (17)C16—C15—C14—C8164.02 (14)
C4—C5—C6—C7126.95 (18)C16—C15—C14—C1339.36 (16)
C6—C5—C10—C1179.96 (15)C16—C17—C20—O2036.5 (2)
C6—C5—C10—C1963.49 (18)C16—C17—C20—C21148.38 (15)
C6—C5—C10—C957.86 (18)C16—C17—O17—C2563.47 (17)
C6—C5—C4—C3176.58 (16)C17—C13—C12—C11168.87 (13)
C6—C7—C8—C14175.11 (14)C17—C13—C14—C8175.55 (13)
C6—C7—C8—C950.38 (19)C17—C13—C14—C1548.31 (15)
C7—C8—C14—C1560.48 (19)C17—O17—C25—O2510.6 (2)
C7—C8—C14—C13179.84 (14)C17—O17—C25—C26169.57 (14)
C8—C7—C6—C546.6 (2)C18—C13—C12—C1167.07 (18)
C8—C9—C10—C1176.89 (13)C18—C13—C14—C861.90 (18)
C8—C9—C10—C559.81 (16)C18—C13—C14—C1565.34 (17)
C8—C9—C10—C1958.30 (18)C18—C13—C17—O17167.93 (13)
C8—C9—C11—O1182.77 (17)C18—C13—C17—C2050.91 (17)
C8—C9—C11—C1242.63 (19)C18—C13—C17—C1678.88 (15)
C9—C8—C14—C15174.80 (13)C20—C17—C16—C2813.2 (2)
C9—C8—C14—C1355.45 (17)C20—C17—C16—C15140.42 (15)
C10—C1—C2—C33.7 (3)C20—C17—O17—C2566.47 (18)
C10—C5—C4—C32.8 (3)C20—C21—O21—C2272.48 (18)
C10—C5—C6—C752.5 (2)C21—O21—C22—O225.0 (2)
C10—C9—C11—O1147.46 (17)C21—O21—C22—C23174.86 (15)
C10—C9—C11—C12172.86 (13)O3—C3—C2—C1171.94 (16)
C10—C9—C8—C14177.52 (14)O3—C3—C4—C5172.31 (16)
C10—C9—C8—C757.75 (17)O17—C17—C16—C28136.25 (15)
C11—C9—C10—C144.61 (18)O17—C17—C16—C1596.56 (14)
C11—C9—C10—C5167.91 (13)O17—C17—C20—O20159.38 (16)
C11—C9—C10—C1973.99 (18)O17—C17—C20—C2125.50 (19)
C11—C9—C8—C1445.18 (19)O17—C25—C26—C27134.57 (16)
C11—C9—C8—C7169.92 (14)O21—C21—C20—O2012.6 (2)
C12—C13—C14—C861.23 (16)O21—C21—C20—C17162.66 (14)
C12—C13—C14—C15171.52 (13)O21—C22—C23—C24139.05 (18)
C12—C13—C17—O1742.05 (18)O22—C22—C23—C2440.8 (3)
C12—C13—C17—C2074.97 (18)O25—C25—C26—C2745.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H11A···O3i0.792.022.7762 (17)161
Symmetry code: (i) x, y+1/2, z+3/2.
 

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