Beclomethasone dipropionate (BDP) is a long-acting inhaled corticosteroid, used for the treatment of asthma, and as an inhalation therapy with HFA-134a. The sample studied by X-ray crystallography was grown in a mixture of the aerosol propellant HFA-134a, C2H2F4, and 200-proof ethanol. The formula of the crystalline material is C28H37ClO7·2C2H6O·C2H2F4. In the crystal structure, disordered solvent occupies a channel which is perpendicular to the BDP molecules. The latter are are stacked together by hydrogen bonding.
Supporting information
CCDC reference: 226945
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.003 Å
Some non-H atoms missing
- R factor = 0.044
- wR factor = 0.099
- Data-to-parameter ratio = 21.5
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 715.20
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
F 19.00 0.00 0.00
Calculated formula weight 521.05
PLAT043_ALERT_1_A Check Reported Molecular Weight ................ 715.20
PLAT044_ALERT_1_A Calculated and Reported Dx Differ .............. ?
PLAT051_ALERT_1_A Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 21.64 Perc.
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.07 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.96 Ratio
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT413_ALERT_2_C Short Inter XH3 .. XHn H25C .. H27B = 2.11 Ang.
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:C34 H51 Cl1 F4 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 C34 H51 Cl F4 O9
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 204.00 168.00 36.00
H 306.00 222.00 84.00
Cl 6.00 6.00 0.00
F 24.00 0.00 24.00
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 27.01
From the CIF: _reflns_number_total 7130
Count of symmetry unique reflns 4019
Completeness (_total/calc) 177.41%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 3111
Fraction of Friedel pairs measured 0.774
Are heavy atom types Z>Si present yes
4 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
8 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997) and SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
C28H37ClO7·2C2H6O·C2H2F4 | Dx = 1.459 Mg m−3 |
Mr = 715.20 | Melting point: 212 K |
Trigonal, P3121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 31 2" | Cell parameters from 8036 reflections |
a = 13.4642 (3) Å | θ = 2.2–21.6° |
c = 31.1187 (15) Å | µ = 0.20 mm−1 |
V = 4885.5 (3) Å3 | T = 170 K |
Z = 6 | Hexagonal block, colorless |
F(000) = 2280 | 0.35 × 0.30 × 0.30 mm |
Data collection top
CCD area detector -I k diffractometer | 7130 independent reflections |
Radiation source: fine-focus sealed tube | 6429 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
phi and ω scans | θmax = 27.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −17→17 |
Tmin = 0.934, Tmax = 0.943 | k = −17→17 |
59064 measured reflections | l = −39→39 |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.7749P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
7130 reflections | Δρmax = 0.44 e Å−3 |
331 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.08 (5) |
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 | 0.53445 (4) | 0.42073 (4) | 0.039377 (14) | 0.02996 (11) | |
O1 | 0.81840 (11) | 0.49657 (12) | 0.10148 (4) | 0.0296 (3) | |
H1B | 0.8854 | 0.5351 | 0.0918 | 0.044* | |
O2 | 0.61194 (12) | 0.02823 (11) | −0.05001 (4) | 0.0302 (3) | |
O3 | 0.64126 (11) | 0.18833 (10) | −0.01671 (4) | 0.0237 (3) | |
O4 | 0.81678 (13) | 0.10357 (12) | 0.03823 (5) | 0.0380 (3) | |
O5 | 0.96831 (12) | 0.23347 (14) | −0.02055 (5) | 0.0405 (4) | |
O6 | 1.01523 (12) | 0.35777 (13) | 0.03365 (5) | 0.0407 (4) | |
O7 | 0.43744 (14) | 0.68576 (15) | 0.11619 (6) | 0.0512 (4) | |
C1 | 0.65903 (17) | 0.61856 (17) | 0.10410 (6) | 0.0310 (4) | |
H1A | 0.7360 | 0.6544 | 0.0942 | 0.037* | |
C2 | 0.60576 (19) | 0.67904 (18) | 0.10262 (7) | 0.0368 (5) | |
H2A | 0.6461 | 0.7560 | 0.0926 | 0.044* | |
C3 | 0.48580 (19) | 0.62932 (19) | 0.11614 (7) | 0.0355 (5) | |
C4 | 0.42812 (17) | 0.51015 (19) | 0.12969 (6) | 0.0322 (4) | |
H4A | 0.3496 | 0.4750 | 0.1377 | 0.039* | |
C5 | 0.47976 (17) | 0.44701 (17) | 0.13150 (6) | 0.0284 (4) | |
C6 | 0.60621 (16) | 0.49760 (16) | 0.12034 (6) | 0.0266 (4) | |
C7 | 0.66879 (17) | 0.50536 (18) | 0.16355 (6) | 0.0312 (4) | |
H7A | 0.6506 | 0.5478 | 0.1847 | 0.047* | |
H7B | 0.7518 | 0.5453 | 0.1587 | 0.047* | |
H7C | 0.6432 | 0.4279 | 0.1743 | 0.047* | |
C8 | 0.61590 (16) | 0.41698 (16) | 0.08635 (6) | 0.0228 (4) | |
C9 | 0.55920 (15) | 0.29235 (16) | 0.10232 (6) | 0.0236 (4) | |
H9A | 0.6024 | 0.2917 | 0.1283 | 0.028* | |
C10 | 0.43440 (16) | 0.24558 (17) | 0.11586 (6) | 0.0303 (4) | |
H10A | 0.4058 | 0.1701 | 0.1299 | 0.036* | |
H10B | 0.3872 | 0.2338 | 0.0899 | 0.036* | |
C11 | 0.41985 (17) | 0.32581 (17) | 0.14677 (6) | 0.0324 (4) | |
H11A | 0.3371 | 0.2990 | 0.1502 | 0.039* | |
H11B | 0.4505 | 0.3224 | 0.1753 | 0.039* | |
C12 | 0.73849 (15) | 0.46217 (15) | 0.06692 (6) | 0.0239 (4) | |
H12A | 0.7579 | 0.5321 | 0.0496 | 0.029* | |
C13 | 0.74733 (16) | 0.37566 (15) | 0.03691 (6) | 0.0247 (4) | |
H13A | 0.7082 | 0.3716 | 0.0095 | 0.030* | |
H13B | 0.8292 | 0.4039 | 0.0304 | 0.030* | |
C14 | 0.69437 (16) | 0.25481 (15) | 0.05611 (5) | 0.0232 (4) | |
C15 | 0.76480 (16) | 0.25017 (17) | 0.09427 (6) | 0.0279 (4) | |
H15A | 0.7608 | 0.2955 | 0.1182 | 0.042* | |
H15B | 0.8449 | 0.2817 | 0.0855 | 0.042* | |
H15C | 0.7335 | 0.1704 | 0.1035 | 0.042* | |
C16 | 0.56923 (15) | 0.21493 (15) | 0.06870 (6) | 0.0230 (4) | |
H16A | 0.5298 | 0.2196 | 0.0422 | 0.028* | |
C17 | 0.51940 (17) | 0.08795 (16) | 0.07884 (6) | 0.0277 (4) | |
H17A | 0.4345 | 0.0470 | 0.0785 | 0.033* | |
H17B | 0.5457 | 0.0772 | 0.1073 | 0.033* | |
C18 | 0.56708 (17) | 0.04541 (16) | 0.04205 (6) | 0.0275 (4) | |
H18A | 0.5076 | 0.0164 | 0.0189 | 0.033* | |
C19 | 0.5807 (2) | −0.05621 (18) | 0.05541 (7) | 0.0371 (5) | |
H19A | 0.5063 | −0.1197 | 0.0646 | 0.056* | |
H19B | 0.6354 | −0.0334 | 0.0792 | 0.056* | |
H19C | 0.6092 | −0.0807 | 0.0310 | 0.056* | |
C20 | 0.67328 (16) | 0.15602 (15) | 0.02347 (5) | 0.0240 (4) | |
C21 | 0.78347 (17) | 0.15279 (16) | 0.01509 (6) | 0.0298 (4) | |
C22 | 0.85919 (17) | 0.2259 (2) | −0.02236 (6) | 0.0354 (5) | |
H22A | 0.8214 | 0.1910 | −0.0500 | 0.042* | |
H22B | 0.8691 | 0.3038 | −0.0208 | 0.042* | |
C23 | 1.03759 (18) | 0.29956 (18) | 0.01143 (7) | 0.0358 (5) | |
C24 | 1.1422 (2) | 0.2878 (2) | 0.01365 (9) | 0.0538 (7) | |
H24A | 1.1173 | 0.2058 | 0.0180 | 0.065* | |
H24B | 1.1817 | 0.3108 | −0.0145 | 0.065* | |
C25 | 1.2247 (3) | 0.3535 (4) | 0.04690 (12) | 0.0927 (12) | |
H25A | 1.2932 | 0.3462 | 0.0435 | 0.139* | |
H25B | 1.1906 | 0.3243 | 0.0752 | 0.139* | |
H25C | 1.2462 | 0.4344 | 0.0445 | 0.139* | |
C26 | 0.61266 (15) | 0.11770 (15) | −0.05082 (6) | 0.0248 (4) | |
C27 | 0.5896 (2) | 0.17061 (17) | −0.08875 (6) | 0.0357 (5) | |
H27A | 0.6614 | 0.2410 | −0.0968 | 0.043* | |
H27B | 0.5330 | 0.1937 | −0.0805 | 0.043* | |
C28 | 0.5451 (2) | 0.0937 (2) | −0.12710 (7) | 0.0528 (7) | |
H28A | 0.5325 | 0.1344 | −0.1507 | 0.079* | |
H28B | 0.4726 | 0.0249 | −0.1198 | 0.079* | |
H28C | 0.6012 | 0.0716 | −0.1360 | 0.079* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0324 (3) | 0.0333 (2) | 0.0260 (2) | 0.0178 (2) | −0.00542 (19) | −0.00066 (19) |
O1 | 0.0196 (6) | 0.0335 (8) | 0.0302 (7) | 0.0091 (6) | −0.0011 (5) | −0.0094 (6) |
O2 | 0.0360 (8) | 0.0232 (7) | 0.0297 (7) | 0.0137 (6) | −0.0004 (6) | −0.0037 (5) |
O3 | 0.0307 (7) | 0.0219 (6) | 0.0170 (6) | 0.0121 (5) | 0.0009 (5) | −0.0013 (5) |
O4 | 0.0391 (8) | 0.0364 (8) | 0.0458 (8) | 0.0243 (7) | 0.0030 (7) | 0.0010 (7) |
O5 | 0.0316 (8) | 0.0483 (9) | 0.0429 (9) | 0.0208 (7) | 0.0053 (7) | −0.0094 (7) |
O6 | 0.0315 (8) | 0.0410 (9) | 0.0496 (9) | 0.0181 (7) | −0.0002 (7) | −0.0076 (7) |
O7 | 0.0477 (10) | 0.0499 (10) | 0.0715 (11) | 0.0361 (9) | −0.0064 (9) | −0.0108 (9) |
C1 | 0.0289 (10) | 0.0279 (10) | 0.0341 (11) | 0.0125 (8) | 0.0038 (8) | −0.0021 (8) |
C2 | 0.0416 (12) | 0.0300 (11) | 0.0412 (12) | 0.0196 (10) | 0.0031 (10) | −0.0022 (9) |
C3 | 0.0407 (12) | 0.0425 (12) | 0.0351 (11) | 0.0296 (10) | −0.0080 (9) | −0.0130 (9) |
C4 | 0.0251 (10) | 0.0437 (12) | 0.0319 (10) | 0.0202 (9) | −0.0022 (8) | −0.0088 (9) |
C5 | 0.0274 (10) | 0.0355 (11) | 0.0215 (9) | 0.0151 (9) | 0.0003 (8) | −0.0046 (8) |
C6 | 0.0263 (9) | 0.0281 (10) | 0.0269 (10) | 0.0148 (8) | −0.0015 (8) | −0.0027 (8) |
C7 | 0.0311 (10) | 0.0410 (12) | 0.0256 (10) | 0.0211 (9) | −0.0019 (8) | −0.0092 (8) |
C8 | 0.0239 (9) | 0.0283 (10) | 0.0190 (9) | 0.0152 (8) | −0.0031 (7) | −0.0024 (7) |
C9 | 0.0227 (9) | 0.0245 (9) | 0.0227 (9) | 0.0112 (8) | 0.0007 (7) | 0.0009 (7) |
C10 | 0.0274 (10) | 0.0295 (10) | 0.0301 (10) | 0.0113 (8) | 0.0047 (8) | 0.0018 (8) |
C11 | 0.0283 (10) | 0.0385 (11) | 0.0317 (10) | 0.0178 (9) | 0.0067 (8) | 0.0026 (9) |
C12 | 0.0226 (9) | 0.0215 (9) | 0.0237 (9) | 0.0081 (7) | 0.0022 (7) | 0.0001 (7) |
C13 | 0.0226 (9) | 0.0230 (9) | 0.0241 (9) | 0.0080 (8) | 0.0046 (7) | −0.0014 (7) |
C14 | 0.0262 (9) | 0.0218 (9) | 0.0186 (8) | 0.0098 (8) | −0.0003 (7) | −0.0006 (7) |
C15 | 0.0277 (10) | 0.0331 (10) | 0.0246 (9) | 0.0164 (8) | −0.0005 (8) | −0.0022 (8) |
C16 | 0.0220 (9) | 0.0218 (9) | 0.0204 (9) | 0.0074 (8) | 0.0024 (7) | 0.0011 (7) |
C17 | 0.0299 (10) | 0.0269 (10) | 0.0232 (9) | 0.0120 (8) | 0.0046 (8) | 0.0026 (8) |
C18 | 0.0320 (10) | 0.0218 (9) | 0.0262 (10) | 0.0114 (8) | 0.0000 (8) | 0.0003 (7) |
C19 | 0.0443 (12) | 0.0274 (11) | 0.0375 (11) | 0.0164 (10) | 0.0070 (9) | 0.0065 (9) |
C20 | 0.0275 (9) | 0.0223 (9) | 0.0212 (9) | 0.0116 (8) | −0.0004 (7) | 0.0000 (7) |
C21 | 0.0337 (11) | 0.0223 (10) | 0.0313 (10) | 0.0124 (9) | −0.0013 (8) | −0.0067 (8) |
C22 | 0.0251 (10) | 0.0439 (12) | 0.0334 (11) | 0.0143 (9) | 0.0015 (8) | −0.0047 (9) |
C23 | 0.0291 (11) | 0.0361 (12) | 0.0401 (12) | 0.0147 (9) | 0.0071 (9) | 0.0064 (10) |
C24 | 0.0392 (13) | 0.0670 (17) | 0.0652 (17) | 0.0340 (13) | 0.0047 (12) | 0.0082 (14) |
C25 | 0.070 (2) | 0.129 (3) | 0.104 (3) | 0.068 (2) | −0.020 (2) | −0.034 (3) |
C26 | 0.0227 (9) | 0.0211 (9) | 0.0230 (9) | 0.0052 (8) | 0.0020 (7) | −0.0008 (7) |
C27 | 0.0518 (13) | 0.0311 (11) | 0.0236 (10) | 0.0203 (10) | 0.0011 (9) | 0.0011 (8) |
C28 | 0.0758 (18) | 0.0425 (13) | 0.0235 (10) | 0.0171 (13) | −0.0094 (11) | 0.0007 (9) |
Geometric parameters (Å, º) top
Cl1—C8 | 1.8430 (17) | C13—C14 | 1.534 (2) |
O1—C12 | 1.425 (2) | C13—H13A | 0.9900 |
O1—H1B | 0.8400 | C13—H13B | 0.9900 |
O2—C26 | 1.200 (2) | C14—C15 | 1.540 (2) |
O3—C26 | 1.347 (2) | C14—C16 | 1.542 (3) |
O3—C20 | 1.458 (2) | C14—C20 | 1.582 (2) |
O4—C21 | 1.207 (2) | C15—H15A | 0.9800 |
O5—C23 | 1.350 (3) | C15—H15B | 0.9800 |
O5—C22 | 1.422 (2) | C15—H15C | 0.9800 |
O6—C23 | 1.191 (2) | C16—C17 | 1.525 (3) |
O7—C3 | 1.223 (3) | C16—H16A | 1.0000 |
C1—C2 | 1.328 (3) | C17—C18 | 1.555 (3) |
C1—C6 | 1.502 (3) | C17—H17A | 0.9900 |
C1—H1A | 0.9500 | C17—H17B | 0.9900 |
C2—C3 | 1.467 (3) | C18—C19 | 1.526 (3) |
C2—H2A | 0.9500 | C18—C20 | 1.571 (3) |
C3—C4 | 1.452 (3) | C18—H18A | 1.0000 |
C4—C5 | 1.342 (3) | C19—H19A | 0.9800 |
C4—H4A | 0.9500 | C19—H19B | 0.9800 |
C5—C11 | 1.491 (3) | C19—H19C | 0.9800 |
C5—C6 | 1.524 (3) | C20—C21 | 1.528 (3) |
C6—C7 | 1.562 (3) | C21—C22 | 1.537 (3) |
C6—C8 | 1.567 (3) | C22—H22A | 0.9900 |
C7—H7A | 0.9800 | C22—H22B | 0.9900 |
C7—H7B | 0.9800 | C23—C24 | 1.496 (3) |
C7—H7C | 0.9800 | C24—C25 | 1.451 (4) |
C8—C9 | 1.538 (3) | C24—H24A | 0.9900 |
C8—C12 | 1.567 (3) | C24—H24B | 0.9900 |
C9—C10 | 1.530 (3) | C25—H25A | 0.9800 |
C9—C16 | 1.530 (3) | C25—H25B | 0.9800 |
C9—H9A | 1.0000 | C25—H25C | 0.9800 |
C10—C11 | 1.530 (3) | C26—C27 | 1.490 (3) |
C10—H10A | 0.9900 | C27—C28 | 1.495 (3) |
C10—H10B | 0.9900 | C27—H27A | 0.9900 |
C11—H11A | 0.9900 | C27—H27B | 0.9900 |
C11—H11B | 0.9900 | C28—H28A | 0.9800 |
C12—C13 | 1.543 (2) | C28—H28B | 0.9800 |
C12—H12A | 1.0000 | C28—H28C | 0.9800 |
| | | |
C12—O1—H1B | 109.5 | H15A—C15—H15B | 109.5 |
C26—O3—C20 | 119.21 (13) | C14—C15—H15C | 109.5 |
C23—O5—C22 | 115.15 (16) | H15A—C15—H15C | 109.5 |
C2—C1—C6 | 124.64 (18) | H15B—C15—H15C | 109.5 |
C2—C1—H1A | 117.7 | C17—C16—C9 | 118.88 (15) |
C6—C1—H1A | 117.7 | C17—C16—C14 | 103.57 (15) |
C1—C2—C3 | 121.28 (19) | C9—C16—C14 | 112.96 (14) |
C1—C2—H2A | 119.4 | C17—C16—H16A | 106.9 |
C3—C2—H2A | 119.4 | C9—C16—H16A | 106.9 |
O7—C3—C4 | 122.0 (2) | C14—C16—H16A | 106.9 |
O7—C3—C2 | 121.6 (2) | C16—C17—C18 | 103.26 (14) |
C4—C3—C2 | 116.48 (17) | C16—C17—H17A | 111.1 |
C5—C4—C3 | 123.50 (18) | C18—C17—H17A | 111.1 |
C5—C4—H4A | 118.3 | C16—C17—H17B | 111.1 |
C3—C4—H4A | 118.3 | C18—C17—H17B | 111.1 |
C4—C5—C11 | 122.60 (18) | H17A—C17—H17B | 109.1 |
C4—C5—C6 | 121.61 (18) | C19—C18—C17 | 112.74 (16) |
C11—C5—C6 | 115.71 (16) | C19—C18—C20 | 119.31 (17) |
C1—C6—C5 | 112.26 (16) | C17—C18—C20 | 105.64 (14) |
C1—C6—C7 | 105.66 (16) | C19—C18—H18A | 106.1 |
C5—C6—C7 | 106.16 (15) | C17—C18—H18A | 106.1 |
C1—C6—C8 | 111.45 (15) | C20—C18—H18A | 106.1 |
C5—C6—C8 | 107.79 (15) | C18—C19—H19A | 109.5 |
C7—C6—C8 | 113.48 (15) | C18—C19—H19B | 109.5 |
C6—C7—H7A | 109.5 | H19A—C19—H19B | 109.5 |
C6—C7—H7B | 109.5 | C18—C19—H19C | 109.5 |
H7A—C7—H7B | 109.5 | H19A—C19—H19C | 109.5 |
C6—C7—H7C | 109.5 | H19B—C19—H19C | 109.5 |
H7A—C7—H7C | 109.5 | O3—C20—C21 | 107.35 (14) |
H7B—C7—H7C | 109.5 | O3—C20—C18 | 109.49 (14) |
C9—C8—C12 | 113.60 (14) | C21—C20—C18 | 118.19 (16) |
C9—C8—C6 | 111.70 (14) | O3—C20—C14 | 104.78 (13) |
C12—C8—C6 | 115.32 (15) | C21—C20—C14 | 111.39 (15) |
C9—C8—Cl1 | 107.98 (12) | C18—C20—C14 | 104.86 (14) |
C12—C8—Cl1 | 102.07 (11) | O4—C21—C20 | 123.13 (18) |
C6—C8—Cl1 | 105.05 (12) | O4—C21—C22 | 119.64 (18) |
C10—C9—C16 | 111.16 (15) | C20—C21—C22 | 116.97 (17) |
C10—C9—C8 | 112.47 (15) | O5—C22—C21 | 110.26 (17) |
C16—C9—C8 | 110.95 (14) | O5—C22—H22A | 109.6 |
C10—C9—H9A | 107.3 | C21—C22—H22A | 109.6 |
C16—C9—H9A | 107.3 | O5—C22—H22B | 109.6 |
C8—C9—H9A | 107.3 | C21—C22—H22B | 109.6 |
C9—C10—C11 | 112.61 (16) | H22A—C22—H22B | 108.1 |
C9—C10—H10A | 109.1 | O6—C23—O5 | 122.89 (19) |
C11—C10—H10A | 109.1 | O6—C23—C24 | 127.1 (2) |
C9—C10—H10B | 109.1 | O5—C23—C24 | 110.0 (2) |
C11—C10—H10B | 109.1 | C25—C24—C23 | 116.3 (2) |
H10A—C10—H10B | 107.8 | C25—C24—H24A | 108.2 |
C5—C11—C10 | 112.47 (16) | C23—C24—H24A | 108.2 |
C5—C11—H11A | 109.1 | C25—C24—H24B | 108.2 |
C10—C11—H11A | 109.1 | C23—C24—H24B | 108.2 |
C5—C11—H11B | 109.1 | H24A—C24—H24B | 107.4 |
C10—C11—H11B | 109.1 | C24—C25—H25A | 109.5 |
H11A—C11—H11B | 107.8 | C24—C25—H25B | 109.5 |
O1—C12—C13 | 111.79 (15) | H25A—C25—H25B | 109.5 |
O1—C12—C8 | 108.23 (13) | C24—C25—H25C | 109.5 |
C13—C12—C8 | 113.83 (15) | H25A—C25—H25C | 109.5 |
O1—C12—H12A | 107.6 | H25B—C25—H25C | 109.5 |
C13—C12—H12A | 107.6 | O2—C26—O3 | 123.25 (17) |
C8—C12—H12A | 107.6 | O2—C26—C27 | 126.70 (17) |
C14—C13—C12 | 113.25 (14) | O3—C26—C27 | 109.96 (15) |
C14—C13—H13A | 108.9 | C26—C27—C28 | 114.11 (17) |
C12—C13—H13A | 108.9 | C26—C27—H27A | 108.7 |
C14—C13—H13B | 108.9 | C28—C27—H27A | 108.7 |
C12—C13—H13B | 108.9 | C26—C27—H27B | 108.7 |
H13A—C13—H13B | 107.7 | C28—C27—H27B | 108.7 |
C13—C14—C15 | 111.97 (15) | H27A—C27—H27B | 107.6 |
C13—C14—C16 | 108.41 (14) | C27—C28—H28A | 109.5 |
C15—C14—C16 | 112.20 (14) | C27—C28—H28B | 109.5 |
C13—C14—C20 | 115.77 (14) | H28A—C28—H28B | 109.5 |
C15—C14—C20 | 108.43 (14) | C27—C28—H28C | 109.5 |
C16—C14—C20 | 99.49 (14) | H28A—C28—H28C | 109.5 |
C14—C15—H15A | 109.5 | H28B—C28—H28C | 109.5 |
C14—C15—H15B | 109.5 | | |
| | | |
C6—C1—C2—C3 | −1.8 (3) | C8—C9—C16—C17 | 179.19 (15) |
C1—C2—C3—O7 | 177.6 (2) | C10—C9—C16—C14 | −176.52 (15) |
C1—C2—C3—C4 | −2.0 (3) | C8—C9—C16—C14 | 57.5 (2) |
O7—C3—C4—C5 | −177.5 (2) | C13—C14—C16—C17 | 169.33 (14) |
C2—C3—C4—C5 | 2.1 (3) | C15—C14—C16—C17 | −66.50 (18) |
C3—C4—C5—C11 | 178.10 (18) | C20—C14—C16—C17 | 47.99 (16) |
C3—C4—C5—C6 | 1.6 (3) | C13—C14—C16—C9 | −60.74 (18) |
C2—C1—C6—C5 | 5.0 (3) | C15—C14—C16—C9 | 63.4 (2) |
C2—C1—C6—C7 | −110.2 (2) | C20—C14—C16—C9 | 177.92 (14) |
C2—C1—C6—C8 | 126.1 (2) | C9—C16—C17—C18 | −169.15 (16) |
C4—C5—C6—C1 | −4.9 (3) | C14—C16—C17—C18 | −42.89 (18) |
C11—C5—C6—C1 | 178.39 (16) | C16—C17—C18—C19 | 151.64 (17) |
C4—C5—C6—C7 | 110.1 (2) | C16—C17—C18—C20 | 19.69 (19) |
C11—C5—C6—C7 | −66.6 (2) | C26—O3—C20—C21 | 64.30 (19) |
C4—C5—C6—C8 | −128.00 (19) | C26—O3—C20—C18 | −65.17 (19) |
C11—C5—C6—C8 | 55.3 (2) | C26—O3—C20—C14 | −177.17 (14) |
C1—C6—C8—C9 | −178.53 (15) | C19—C18—C20—O3 | 129.58 (17) |
C5—C6—C8—C9 | −54.92 (18) | C17—C18—C20—O3 | −102.29 (16) |
C7—C6—C8—C9 | 62.3 (2) | C19—C18—C20—C21 | 6.3 (2) |
C1—C6—C8—C12 | 49.8 (2) | C17—C18—C20—C21 | 134.43 (17) |
C5—C6—C8—C12 | 173.40 (15) | C19—C18—C20—C14 | −118.47 (18) |
C7—C6—C8—C12 | −69.3 (2) | C17—C18—C20—C14 | 9.66 (18) |
C1—C6—C8—Cl1 | −61.72 (17) | C13—C14—C20—O3 | −35.2 (2) |
C5—C6—C8—Cl1 | 61.89 (16) | C15—C14—C20—O3 | −162.00 (14) |
C7—C6—C8—Cl1 | 179.15 (13) | C16—C14—C20—O3 | 80.65 (15) |
C12—C8—C9—C10 | −172.82 (14) | C13—C14—C20—C21 | 80.54 (19) |
C6—C8—C9—C10 | 54.64 (19) | C15—C14—C20—C21 | −46.2 (2) |
Cl1—C8—C9—C10 | −60.38 (17) | C16—C14—C20—C21 | −163.59 (15) |
C12—C8—C9—C16 | −47.61 (19) | C13—C14—C20—C18 | −150.50 (16) |
C6—C8—C9—C16 | 179.85 (14) | C15—C14—C20—C18 | 82.72 (17) |
Cl1—C8—C9—C16 | 64.83 (16) | C16—C14—C20—C18 | −34.63 (16) |
C16—C9—C10—C11 | −175.38 (16) | O3—C20—C21—O4 | −161.75 (17) |
C8—C9—C10—C11 | −50.3 (2) | C18—C20—C21—O4 | −37.4 (3) |
C4—C5—C11—C10 | 130.4 (2) | C14—C20—C21—O4 | 84.1 (2) |
C6—C5—C11—C10 | −52.9 (2) | O3—C20—C21—C22 | 24.2 (2) |
C9—C10—C11—C5 | 48.3 (2) | C18—C20—C21—C22 | 148.51 (16) |
C9—C8—C12—O1 | −81.26 (17) | C14—C20—C21—C22 | −90.00 (19) |
C6—C8—C12—O1 | 49.51 (19) | C23—O5—C22—C21 | −71.8 (2) |
Cl1—C8—C12—O1 | 162.77 (12) | O4—C21—C22—O5 | −6.6 (3) |
C9—C8—C12—C13 | 43.7 (2) | C20—C21—C22—O5 | 167.73 (16) |
C6—C8—C12—C13 | 174.46 (15) | C22—O5—C23—O6 | −8.1 (3) |
Cl1—C8—C12—C13 | −72.28 (16) | C22—O5—C23—C24 | 172.28 (19) |
O1—C12—C13—C14 | 75.01 (19) | O6—C23—C24—C25 | 0.8 (4) |
C8—C12—C13—C14 | −48.0 (2) | O5—C23—C24—C25 | −179.5 (3) |
C12—C13—C14—C15 | −69.2 (2) | C20—O3—C26—O2 | 0.1 (3) |
C12—C13—C14—C16 | 55.09 (19) | C20—O3—C26—C27 | −176.86 (15) |
C12—C13—C14—C20 | 165.79 (15) | O2—C26—C27—C28 | 9.3 (3) |
C10—C9—C16—C17 | −54.9 (2) | O3—C26—C27—C28 | −173.92 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O2i | 0.84 | 2.11 | 2.9276 (18) | 163 |
Symmetry code: (i) y+1, x, −z. |