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
CCDC reference: 189884
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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.
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.
9
α-chloro-16
β-methyl-3,20-dioxo-1,4-pregnadiene-11
β,17,21-triol
17,21-dipropionate
top
Crystal data top
C28H37ClO7 | Dx = 1.362 Mg m−3 |
Mr = 521.03 | Melting point: 486.70 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5087 reflections |
a = 12.1239 (15) Å | θ = 5.7–51.3° |
b = 14.1289 (17) Å | µ = 0.20 mm−1 |
c = 14.8381 (18) Å | T = 100 K |
V = 2541.7 (5) Å3 | Irregular block, colorless |
Z = 4 | 0.40 × 0.30 × 0.25 mm |
F(000) = 1112 | |
Data collection top
Bruker CCD area-detector diffractometer | 4799 independent reflections |
Radiation source: fine-focus sealed tube | 4507 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 8.192 pixels mm-1 | θmax = 25.7°, θmin = 2.0° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −17→17 |
Tmin = 0.923, Tmax = 0.952 | l = −18→18 |
25323 measured reflections | |
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)] = 0.030 | H 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 reflections | Δρmax = 0.25 e Å−3 |
331 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Absolute structure: (Flack, 1983), 2086 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.15059 (3) | 0.33651 (3) | 0.93011 (3) | 0.01699 (10) | |
C1 | −0.05521 (14) | 0.38287 (12) | 0.80701 (12) | 0.0168 (4) | |
C2 | −0.09520 (14) | 0.29623 (12) | 0.79205 (12) | 0.0176 (4) | |
C3 | −0.12659 (14) | 0.23459 (12) | 0.86672 (12) | 0.0176 (4) | |
C4 | −0.12420 (14) | 0.27555 (12) | 0.95735 (12) | 0.0180 (4) | |
C5 | −0.08493 (14) | 0.36275 (12) | 0.97369 (12) | 0.0180 (4) | |
C6 | −0.07631 (15) | 0.40361 (13) | 1.06706 (12) | 0.0207 (4) | |
C7 | 0.03977 (15) | 0.44053 (12) | 1.08833 (11) | 0.0185 (4) | |
C8 | 0.08850 (13) | 0.50151 (12) | 1.01263 (11) | 0.0149 (3) | |
C9 | 0.07953 (14) | 0.45151 (11) | 0.92098 (12) | 0.0149 (3) | |
C10 | −0.04490 (14) | 0.42699 (11) | 0.89877 (11) | 0.0157 (4) | |
C11 | 0.14463 (14) | 0.49978 (11) | 0.84280 (11) | 0.0152 (3) | |
C12 | 0.26046 (14) | 0.53354 (12) | 0.87083 (12) | 0.0154 (4) | |
C13 | 0.25939 (13) | 0.59114 (11) | 0.95880 (11) | 0.0149 (3) | |
C14 | 0.20708 (14) | 0.52942 (11) | 1.03312 (12) | 0.0152 (3) | |
C15 | 0.22708 (14) | 0.58732 (12) | 1.11812 (12) | 0.0177 (4) | |
C16 | 0.34446 (16) | 0.62867 (11) | 1.10645 (12) | 0.0181 (4) | |
C17 | 0.37384 (14) | 0.61333 (11) | 1.00403 (12) | 0.0158 (4) | |
C18 | 0.19869 (14) | 0.68661 (11) | 0.94580 (12) | 0.0173 (4) | |
C19 | −0.12088 (15) | 0.51637 (12) | 0.89719 (12) | 0.0200 (4) | |
C20 | 0.43572 (14) | 0.69070 (12) | 0.95290 (12) | 0.0176 (4) | |
C21 | 0.51340 (15) | 0.65787 (13) | 0.87765 (12) | 0.0216 (4) | |
C22 | 0.45698 (15) | 0.76157 (13) | 0.76372 (12) | 0.0222 (4) | |
C23 | 0.48661 (17) | 0.84763 (15) | 0.70912 (14) | 0.0322 (5) | |
C24 | 0.3901 (2) | 0.91434 (16) | 0.70450 (18) | 0.0476 (7) | |
C25 | 0.53772 (14) | 0.52588 (11) | 1.03982 (12) | 0.0180 (4) | |
C26 | 0.59007 (14) | 0.42939 (12) | 1.04460 (12) | 0.0199 (4) | |
C27 | 0.63507 (16) | 0.41014 (13) | 1.13868 (12) | 0.0235 (4) | |
C28 | 0.35578 (16) | 0.72816 (12) | 1.14641 (12) | 0.0217 (4) | |
H1 | −0.0318 | 0.4189 | 0.7564 | 0.02* | |
H2 | −0.1034 | 0.2744 | 0.7319 | 0.021* | |
H4 | −0.1514 | 0.2391 | 1.0064 | 0.022* | |
H6A | −0.0963 | 0.3543 | 1.1115 | 0.025* | |
H6B | −0.1298 | 0.4562 | 1.0732 | 0.025* | |
H7A | 0.0892 | 0.386 | 1.0993 | 0.022* | |
H7B | 0.0369 | 0.4785 | 1.1444 | 0.022* | |
H8 | 0.044 | 0.561 | 1.0091 | 0.018* | |
H11 | 0.1541 | 0.4517 | 0.7939 | 0.018* | |
H11A | 0.1137 | 0.5921 | 0.7657 | 0.036 (7)* | |
H12A | 0.309 | 0.4778 | 0.8787 | 0.018* | |
H12B | 0.2918 | 0.573 | 0.822 | 0.018* | |
H14 | 0.2515 | 0.47 | 1.038 | 0.018* | |
H15A | 0.2231 | 0.5467 | 1.1724 | 0.021* | |
H15B | 0.1719 | 0.6386 | 1.1237 | 0.021* | |
H16 | 0.3952 | 0.5869 | 1.1417 | 0.022* | |
H18A | 0.2288 | 0.7193 | 0.893 | 0.026* | |
H18B | 0.2091 | 0.7261 | 0.9994 | 0.026* | |
H18C | 0.1198 | 0.6749 | 0.9367 | 0.026* | |
H19A | −0.0993 | 0.5575 | 0.847 | 0.03* | |
H19B | −0.1132 | 0.5509 | 0.9541 | 0.03* | |
H19C | −0.1978 | 0.4967 | 0.8895 | 0.03* | |
H21A | 0.582 | 0.6323 | 0.9045 | 0.026* | |
H21B | 0.4777 | 0.6065 | 0.8429 | 0.026* | |
H23A | 0.5504 | 0.8801 | 0.7371 | 0.039* | |
H23B | 0.508 | 0.8282 | 0.6475 | 0.039* | |
H24A | 0.3273 | 0.8822 | 0.6764 | 0.071* | |
H24B | 0.4102 | 0.9699 | 0.6686 | 0.071* | |
H24C | 0.3699 | 0.9344 | 0.7655 | 0.071* | |
H26A | 0.6508 | 0.4254 | 1.0002 | 0.024* | |
H26B | 0.5347 | 0.3806 | 1.029 | 0.024* | |
H27A | 0.6842 | 0.4619 | 1.1566 | 0.035* | |
H27B | 0.6762 | 0.3504 | 1.1385 | 0.035* | |
H27C | 0.5737 | 0.4057 | 1.1815 | 0.035* | |
H28A | 0.3035 | 0.7709 | 1.1167 | 0.033* | |
H28B | 0.4311 | 0.7512 | 1.137 | 0.033* | |
H28C | 0.3399 | 0.726 | 1.2111 | 0.033* | |
O3 | −0.15232 (11) | 0.15042 (8) | 0.85435 (8) | 0.0222 (3) | |
O11 | 0.07910 (10) | 0.57439 (8) | 0.80748 (8) | 0.0192 (3) | |
O17 | 0.43926 (9) | 0.52555 (8) | 0.99752 (8) | 0.0162 (3) | |
O20 | 0.42063 (10) | 0.77456 (8) | 0.96527 (8) | 0.0211 (3) | |
O21 | 0.54011 (10) | 0.73429 (9) | 0.81850 (9) | 0.0229 (3) | |
O22 | 0.37005 (11) | 0.72110 (9) | 0.76001 (9) | 0.0287 (3) | |
O25 | 0.57913 (10) | 0.59710 (8) | 1.07041 (9) | 0.0234 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0193 (2) | 0.01071 (17) | 0.0210 (2) | 0.00139 (15) | −0.00019 (17) | 0.00014 (16) |
C1 | 0.0153 (8) | 0.0175 (9) | 0.0175 (9) | 0.0007 (7) | 0.0014 (7) | 0.0008 (7) |
C2 | 0.0167 (9) | 0.0186 (9) | 0.0176 (9) | 0.0001 (7) | −0.0007 (7) | −0.0038 (7) |
C3 | 0.0147 (8) | 0.0146 (8) | 0.0236 (9) | −0.0001 (7) | −0.0004 (7) | −0.0013 (7) |
C4 | 0.0175 (8) | 0.0158 (8) | 0.0208 (9) | −0.0022 (7) | 0.0035 (7) | 0.0020 (7) |
C5 | 0.0139 (8) | 0.0182 (8) | 0.0218 (9) | 0.0002 (7) | 0.0021 (7) | −0.0022 (7) |
C6 | 0.0230 (9) | 0.0192 (8) | 0.0200 (9) | −0.0032 (7) | 0.0059 (8) | −0.0009 (8) |
C7 | 0.0233 (9) | 0.0188 (8) | 0.0133 (9) | −0.0020 (7) | 0.0010 (7) | −0.0009 (7) |
C8 | 0.0162 (8) | 0.0117 (8) | 0.0169 (9) | −0.0007 (7) | 0.0000 (7) | 0.0002 (7) |
C9 | 0.0165 (8) | 0.0087 (7) | 0.0194 (9) | 0.0013 (6) | −0.0014 (7) | 0.0001 (7) |
C10 | 0.0172 (9) | 0.0117 (8) | 0.0183 (9) | −0.0006 (7) | 0.0000 (7) | −0.0010 (7) |
C11 | 0.0181 (8) | 0.0128 (7) | 0.0147 (8) | −0.0006 (7) | 0.0008 (7) | 0.0007 (6) |
C12 | 0.0170 (9) | 0.0128 (8) | 0.0164 (9) | −0.0005 (6) | 0.0004 (7) | 0.0012 (7) |
C13 | 0.0160 (8) | 0.0123 (8) | 0.0164 (9) | −0.0009 (7) | −0.0013 (7) | −0.0009 (7) |
C14 | 0.0174 (8) | 0.0109 (8) | 0.0172 (9) | 0.0017 (6) | −0.0003 (7) | −0.0009 (7) |
C15 | 0.0204 (9) | 0.0161 (9) | 0.0168 (9) | 0.0002 (7) | −0.0008 (7) | −0.0013 (7) |
C16 | 0.0200 (9) | 0.0144 (8) | 0.0199 (9) | 0.0009 (7) | −0.0022 (7) | −0.0004 (7) |
C17 | 0.0185 (9) | 0.0087 (8) | 0.0203 (9) | 0.0020 (6) | −0.0012 (7) | −0.0011 (6) |
C18 | 0.0190 (9) | 0.0130 (8) | 0.0199 (9) | 0.0003 (6) | −0.0029 (7) | −0.0002 (7) |
C19 | 0.0192 (9) | 0.0154 (8) | 0.0255 (10) | 0.0009 (7) | −0.0008 (7) | −0.0019 (7) |
C20 | 0.0145 (8) | 0.0172 (8) | 0.0213 (9) | −0.0014 (6) | −0.0070 (7) | 0.0005 (7) |
C21 | 0.0229 (9) | 0.0163 (8) | 0.0257 (10) | −0.0020 (7) | −0.0002 (8) | 0.0030 (8) |
C22 | 0.0267 (10) | 0.0207 (9) | 0.0191 (9) | −0.0042 (8) | 0.0023 (8) | −0.0019 (8) |
C23 | 0.0375 (12) | 0.0316 (11) | 0.0276 (11) | −0.0128 (9) | −0.0015 (9) | 0.0057 (9) |
C24 | 0.0445 (14) | 0.0301 (12) | 0.0682 (17) | −0.0098 (11) | −0.0144 (12) | 0.0223 (12) |
C25 | 0.0183 (8) | 0.0169 (9) | 0.0188 (9) | 0.0001 (7) | 0.0015 (7) | 0.0024 (7) |
C26 | 0.0189 (9) | 0.0158 (8) | 0.0250 (10) | 0.0023 (7) | 0.0016 (7) | −0.0025 (7) |
C27 | 0.0230 (9) | 0.0192 (9) | 0.0282 (10) | 0.0021 (8) | 0.0002 (8) | 0.0022 (8) |
C28 | 0.0258 (9) | 0.0182 (8) | 0.0212 (9) | −0.0036 (8) | −0.0021 (8) | −0.0042 (7) |
O3 | 0.0277 (7) | 0.0125 (6) | 0.0263 (7) | −0.0027 (5) | 0.0013 (6) | −0.0027 (5) |
O11 | 0.0202 (6) | 0.0171 (6) | 0.0203 (7) | −0.0010 (5) | −0.0019 (5) | 0.0045 (5) |
O17 | 0.0169 (6) | 0.0108 (6) | 0.0209 (6) | 0.0013 (5) | −0.0020 (5) | −0.0013 (5) |
O20 | 0.0256 (7) | 0.0118 (6) | 0.0259 (7) | −0.0029 (5) | −0.0028 (5) | −0.0003 (5) |
O21 | 0.0233 (7) | 0.0212 (6) | 0.0242 (7) | −0.0068 (5) | 0.0014 (5) | 0.0048 (6) |
O22 | 0.0287 (8) | 0.0275 (7) | 0.0299 (7) | −0.0087 (6) | −0.0036 (6) | 0.0059 (6) |
O25 | 0.0216 (6) | 0.0155 (6) | 0.0330 (7) | −0.0023 (5) | −0.0064 (6) | −0.0015 (6) |
Geometric parameters (Å, º) top
Cl1—C9 | 1.8440 (16) | C16—H16 | 1 |
C1—C10 | 1.503 (2) | C17—C16 | 1.576 (2) |
C1—C2 | 1.335 (2) | C17—C20 | 1.528 (2) |
C1—H1 | 0.95 | C17—O17 | 1.4752 (19) |
C2—H2 | 0.95 | C18—H18A | 0.98 |
C3—C2 | 1.460 (2) | C18—H18B | 0.98 |
C3—C4 | 1.464 (2) | C18—H18C | 0.98 |
C3—O3 | 1.243 (2) | C19—C10 | 1.563 (2) |
C4—H4 | 0.95 | C19—H19A | 0.98 |
C5—C10 | 1.515 (2) | C19—H19B | 0.98 |
C5—C4 | 1.343 (2) | C19—H19C | 0.98 |
C5—C6 | 1.504 (3) | C21—C20 | 1.533 (2) |
C6—H6A | 0.99 | C21—H21A | 0.99 |
C6—H6B | 0.99 | C21—H21B | 0.99 |
C7—C6 | 1.534 (2) | C21—O21 | 1.429 (2) |
C7—C8 | 1.534 (2) | C22—C23 | 1.505 (3) |
C7—H7A | 0.99 | C23—C24 | 1.504 (3) |
C7—H7B | 0.99 | C23—H23A | 0.99 |
C8—C14 | 1.521 (2) | C23—H23B | 0.99 |
C8—H8 | 1 | C24—H24A | 0.98 |
C9—C10 | 1.583 (2) | C24—H24B | 0.98 |
C9—C11 | 1.560 (2) | C24—H24C | 0.98 |
C9—C8 | 1.536 (2) | C25—C26 | 1.505 (2) |
C11—H11 | 1 | C26—C27 | 1.523 (3) |
C11—O11 | 1.420 (2) | C26—H26A | 0.99 |
C12—C11 | 1.540 (2) | C26—H26B | 0.99 |
C12—H12A | 0.99 | C27—H27A | 0.98 |
C12—H12B | 0.99 | C27—H27B | 0.98 |
C13—C12 | 1.538 (2) | C27—H27C | 0.98 |
C13—C14 | 1.542 (2) | C28—H28A | 0.98 |
C13—C17 | 1.573 (2) | C28—H28B | 0.98 |
C13—C18 | 1.549 (2) | C28—H28C | 0.98 |
C14—H14 | 1 | O17—C25 | 1.349 (2) |
C15—C14 | 1.523 (2) | O20—C20 | 1.213 (2) |
C15—C16 | 1.548 (3) | O21—C22 | 1.351 (2) |
C15—H15A | 0.99 | O22—C22 | 1.200 (2) |
C15—H15B | 0.99 | O25—C25 | 1.213 (2) |
C16—C28 | 1.532 (2) | | |
| | | |
C1—C10—C19 | 105.81 (14) | C16—C28—H28A | 109.5 |
C1—C10—C5 | 112.93 (14) | C16—C28—H28B | 109.5 |
C1—C10—C9 | 111.03 (14) | C16—C28—H28C | 109.5 |
C1—C2—C3 | 121.02 (16) | C17—C16—H16 | 106.5 |
C1—C2—H2 | 119.5 | C17—C20—C21 | 116.56 (14) |
C2—C1—C10 | 124.14 (16) | C18—C13—C17 | 107.39 (13) |
C2—C1—H1 | 117.9 | C19—C10—C9 | 112.83 (13) |
C2—C3—C4 | 117.14 (14) | C20—C17—C13 | 111.34 (14) |
C3—C2—H2 | 119.5 | C20—C17—C16 | 119.45 (14) |
C3—C4—H4 | 118.8 | C20—C21—H21A | 109.4 |
C4—C5—C10 | 122.06 (16) | C20—C21—H21B | 109.4 |
C4—C5—C6 | 122.89 (16) | C22—C23—H23A | 109.6 |
C5—C10—C19 | 107.83 (14) | C22—C23—H23B | 109.6 |
C5—C10—C9 | 106.48 (14) | C22—O21—C21 | 114.59 (13) |
C5—C4—C3 | 122.37 (16) | C23—C24—H24A | 109.5 |
C5—C4—H4 | 118.8 | C23—C24—H24B | 109.5 |
C5—C6—C7 | 112.57 (14) | C23—C24—H24C | 109.5 |
C5—C6—H6A | 109.1 | C24—C23—C22 | 110.20 (17) |
C5—C6—H6B | 109.1 | C24—C23—H23A | 109.6 |
C6—C5—C10 | 115.06 (14) | C24—C23—H23B | 109.6 |
C6—C7—C8 | 113.19 (14) | C25—C26—C27 | 110.85 (15) |
C6—C7—H7A | 108.9 | C25—C26—H26A | 109.5 |
C6—C7—H7B | 108.9 | C25—C26—H26B | 109.5 |
C7—C6—H6A | 109.1 | C25—O17—C17 | 116.26 (12) |
C7—C6—H6B | 109.1 | C26—C27—H27A | 109.5 |
C7—C8—C9 | 111.26 (13) | C26—C27—H27B | 109.5 |
C7—C8—H8 | 107.6 | C26—C27—H27C | 109.5 |
C8—C14—C13 | 113.09 (14) | C27—C26—H26A | 109.5 |
C8—C14—C15 | 117.08 (14) | C27—C26—H26B | 109.5 |
C8—C14—H14 | 107.8 | C28—C16—C15 | 112.67 (15) |
C8—C7—H7A | 108.9 | C28—C16—C17 | 118.63 (14) |
C8—C7—H7B | 108.9 | C28—C16—H16 | 106.5 |
C8—C9—C10 | 110.64 (13) | H6A—C6—H6B | 107.8 |
C8—C9—C11 | 114.92 (13) | H7A—C7—H7B | 107.8 |
C8—C9—Cl1 | 107.89 (11) | H12A—C12—H12B | 107.8 |
C9—C11—H11 | 107.5 | H15A—C15—H15B | 108.8 |
C9—C8—H8 | 107.6 | H18A—C18—H18B | 109.5 |
C10—C1—H1 | 117.9 | H18A—C18—H18C | 109.5 |
C10—C19—H19A | 109.5 | H18B—C18—H18C | 109.5 |
C10—C19—H19B | 109.5 | H19A—C19—H19B | 109.5 |
C10—C19—H19C | 109.5 | H19A—C19—H19C | 109.5 |
C10—C9—Cl1 | 105.53 (11) | H19B—C19—H19C | 109.5 |
C11—C12—H12A | 109.1 | H21A—C21—H21B | 108 |
C11—C12—H12B | 109.1 | H23A—C23—H23B | 108.1 |
C11—C9—C10 | 115.03 (14) | H24A—C24—H24B | 109.5 |
C11—C9—Cl1 | 101.74 (11) | H24A—C24—H24C | 109.5 |
C12—C11—C9 | 113.31 (13) | H24B—C24—H24C | 109.5 |
C12—C11—H11 | 107.5 | H26A—C26—H26B | 108.1 |
C12—C13—C14 | 108.12 (13) | H27A—C27—H27B | 109.5 |
C12—C13—C17 | 117.39 (13) | H27A—C27—H27C | 109.5 |
C12—C13—C18 | 111.05 (13) | H27B—C27—H27C | 109.5 |
C13—C12—C11 | 112.66 (13) | H28A—C28—H28B | 109.5 |
C13—C12—H12A | 109.1 | H28A—C28—H28C | 109.5 |
C13—C12—H12B | 109.1 | H28B—C28—H28C | 109.5 |
C13—C14—H14 | 107.8 | O3—C3—C2 | 121.61 (16) |
C13—C17—C16 | 103.85 (14) | O3—C3—C4 | 121.24 (15) |
C13—C18—H18A | 109.5 | O11—C11—C12 | 112.32 (13) |
C13—C18—H18B | 109.5 | O11—C11—C9 | 108.42 (13) |
C13—C18—H18C | 109.5 | O11—C11—H11 | 107.5 |
C14—C13—C17 | 99.80 (13) | O17—C17—C13 | 106.19 (12) |
C14—C13—C18 | 112.71 (14) | O17—C17—C16 | 107.48 (13) |
C14—C15—C16 | 104.86 (14) | O17—C17—C20 | 107.76 (13) |
C14—C15—H15A | 110.8 | O17—C25—C26 | 113.08 (14) |
C14—C15—H15B | 110.8 | O20—C20—C17 | 123.35 (16) |
C14—C8—C7 | 111.29 (14) | O20—C20—C21 | 119.91 (16) |
C14—C8—C9 | 111.29 (13) | O21—C21—C20 | 110.99 (14) |
C14—C8—H8 | 107.6 | O21—C21—H21A | 109.4 |
C15—C14—C13 | 102.88 (13) | O21—C21—H21B | 109.4 |
C15—C14—H14 | 107.8 | O21—C22—C23 | 112.11 (15) |
C15—C16—C17 | 105.29 (14) | O22—C22—C23 | 124.74 (17) |
C15—C16—H16 | 106.5 | O22—C22—O21 | 123.15 (16) |
C16—C15—H15A | 110.8 | O25—C25—C26 | 124.00 (16) |
C16—C15—H15B | 110.8 | O25—C25—O17 | 122.92 (15) |
| | | |
Cl1—C9—C10—C1 | −66.66 (15) | C12—C13—C17—C16 | −155.24 (13) |
Cl1—C9—C10—C5 | 56.64 (14) | C13—C12—C11—O11 | 74.33 (17) |
Cl1—C9—C10—C19 | 174.74 (12) | C13—C12—C11—C9 | −48.96 (18) |
Cl1—C9—C11—O11 | 160.97 (10) | C13—C17—C16—C28 | −111.50 (17) |
Cl1—C9—C11—C12 | −73.63 (14) | C13—C17—C16—C15 | 15.70 (16) |
Cl1—C9—C8—C14 | 67.51 (15) | C13—C17—C20—O20 | 84.6 (2) |
Cl1—C9—C8—C7 | −57.23 (16) | C13—C17—C20—C21 | −90.57 (17) |
C2—C1—C10—C5 | 0.0 (2) | C13—C17—O17—C25 | −174.13 (13) |
C2—C1—C10—C19 | −117.78 (18) | C14—C13—C12—C11 | 57.07 (17) |
C2—C1—C10—C9 | 119.47 (18) | C14—C13—C17—O17 | 74.37 (14) |
C2—C3—C4—C5 | −6.4 (2) | C14—C13—C17—C20 | −168.60 (13) |
C4—C3—C2—C1 | 6.8 (2) | C14—C13—C17—C16 | −38.81 (15) |
C4—C5—C10—C1 | 0.5 (2) | C14—C15—C16—C28 | 144.82 (14) |
C4—C5—C10—C19 | 117.05 (17) | C14—C15—C16—C17 | 14.08 (17) |
C4—C5—C10—C9 | −121.60 (17) | C16—C15—C14—C8 | −164.02 (14) |
C4—C5—C6—C7 | 126.95 (18) | C16—C15—C14—C13 | −39.36 (16) |
C6—C5—C10—C1 | 179.96 (15) | C16—C17—C20—O20 | −36.5 (2) |
C6—C5—C10—C19 | −63.49 (18) | C16—C17—C20—C21 | 148.38 (15) |
C6—C5—C10—C9 | 57.86 (18) | C16—C17—O17—C25 | −63.47 (17) |
C6—C5—C4—C3 | −176.58 (16) | C17—C13—C12—C11 | 168.87 (13) |
C6—C7—C8—C14 | −175.11 (14) | C17—C13—C14—C8 | 175.55 (13) |
C6—C7—C8—C9 | −50.38 (19) | C17—C13—C14—C15 | 48.31 (15) |
C7—C8—C14—C15 | −60.48 (19) | C17—O17—C25—O25 | −10.6 (2) |
C7—C8—C14—C13 | −179.84 (14) | C17—O17—C25—C26 | 169.57 (14) |
C8—C7—C6—C5 | 46.6 (2) | C18—C13—C12—C11 | −67.07 (18) |
C8—C9—C10—C1 | 176.89 (13) | C18—C13—C14—C8 | 61.90 (18) |
C8—C9—C10—C5 | −59.81 (16) | C18—C13—C14—C15 | −65.34 (17) |
C8—C9—C10—C19 | 58.30 (18) | C18—C13—C17—O17 | −167.93 (13) |
C8—C9—C11—O11 | −82.77 (17) | C18—C13—C17—C20 | −50.91 (17) |
C8—C9—C11—C12 | 42.63 (19) | C18—C13—C17—C16 | 78.88 (15) |
C9—C8—C14—C15 | 174.80 (13) | C20—C17—C16—C28 | 13.2 (2) |
C9—C8—C14—C13 | 55.45 (17) | C20—C17—C16—C15 | 140.42 (15) |
C10—C1—C2—C3 | −3.7 (3) | C20—C17—O17—C25 | 66.47 (18) |
C10—C5—C4—C3 | 2.8 (3) | C20—C21—O21—C22 | −72.48 (18) |
C10—C5—C6—C7 | −52.5 (2) | C21—O21—C22—O22 | −5.0 (2) |
C10—C9—C11—O11 | 47.46 (17) | C21—O21—C22—C23 | 174.86 (15) |
C10—C9—C11—C12 | 172.86 (13) | O3—C3—C2—C1 | −171.94 (16) |
C10—C9—C8—C14 | −177.52 (14) | O3—C3—C4—C5 | 172.31 (16) |
C10—C9—C8—C7 | 57.75 (17) | O17—C17—C16—C28 | 136.25 (15) |
C11—C9—C10—C1 | 44.61 (18) | O17—C17—C16—C15 | −96.56 (14) |
C11—C9—C10—C5 | 167.91 (13) | O17—C17—C20—O20 | −159.38 (16) |
C11—C9—C10—C19 | −73.99 (18) | O17—C17—C20—C21 | 25.50 (19) |
C11—C9—C8—C14 | −45.18 (19) | O17—C25—C26—C27 | −134.57 (16) |
C11—C9—C8—C7 | −169.92 (14) | O21—C21—C20—O20 | −12.6 (2) |
C12—C13—C14—C8 | −61.23 (16) | O21—C21—C20—C17 | 162.66 (14) |
C12—C13—C14—C15 | 171.52 (13) | O21—C22—C23—C24 | −139.05 (18) |
C12—C13—C17—O17 | −42.05 (18) | O22—C22—C23—C24 | 40.8 (3) |
C12—C13—C17—C20 | 74.97 (18) | O25—C25—C26—C27 | 45.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11A···O3i | 0.79 | 2.02 | 2.7762 (17) | 161 |
Symmetry code: (i) −x, y+1/2, −z+3/2. |