In the title compound [systematic name: 6,7,9,10,12,13,15,16-octahydrodibenzo[
n,
q][1,4,7,10,13,16]pentaoxathiacyclooctadecine antimony(III) trifluoride clathrate], (C
20H
24O
5S)SbF
3], the components are held together
via electrostatic interactions between the antimony lone pair and the collective electron system of the macrocycle. The antimony trifluoride molecule is situated in a perching mode above the macrocyclic cavity, its coordination being completed by three crown ether O atoms at distances in the range 2.737 (1)–3.136 (1) Å. Neighboring 1:1 adducts are linked into chains
via C—H
F hydrogen bonds.
Supporting information
CCDC reference: 608428
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.019
- wR factor = 0.045
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT301_ALERT_3_C Main Residue Disorder ......................... 19.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact F1 .. O5 .. 2.90 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact F1 .. O4A .. 2.92 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact F2 .. O4A .. 2.84 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact F3 .. O2 .. 2.90 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.10 Deg.
C5 -O3 -C5A 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.72 Deg.
O5 -C9 -O5A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response:
Response: All authors made significant contribution
in this work. The idea of synthesis of the initial crown ether belongs to
Kamalov and Kotlyar. The idea of synthesis of the complex
belongs to Gelmboldt and Ganin. The synthesis of crown ether
was performed by Kotlyar.
The synthesis of the complex was performed by Ganin.
X-ray diffraction experiment was performed by Lipkowski.
The analysis of diffraction data was performed by Fonari.
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: COLLECT (Nonius, 1998); cell refinement: COLLECT and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT and DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
6,7,9,10,12,13,15,16-
octahydrodibenzo[n,q][1,4,7,10,13,16]pentaoxathiacyclooctadecine antimony(III)
trifluoride clathrate
top
Crystal data top
(C20H24O5S)[SbF3] | Dx = 1.726 Mg m−3 |
Mr = 555.20 | Melting point: 463 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5980 (2) Å | Cell parameters from 9674 reflections |
b = 16.2930 (2) Å | θ = 1–27.5° |
c = 13.2860 (2) Å | µ = 1.44 mm−1 |
β = 111.3760 (9)° | T = 123 K |
V = 2136.32 (6) Å3 | Prism, yellow |
Z = 4 | 0.15 × 0.12 × 0.10 mm |
F(000) = 1112 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 3952 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 26.0°, θmin = 2.4° |
φ–ω scans | h = −13→13 |
16182 measured reflections | k = −20→20 |
4190 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.019 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.046 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0225P)2 + 2.0901P] where P = (Fo2 + 2Fc2)/3 |
4190 reflections | (Δ/σ)max = 0.001 |
296 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
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 | Occ. (<1) |
Sb1 | 0.547592 (12) | 0.149699 (7) | 0.265930 (9) | 0.01632 (5) | |
F1 | 0.48231 (11) | 0.26212 (6) | 0.24813 (9) | 0.0253 (2) | |
F2 | 0.72626 (11) | 0.19053 (7) | 0.28737 (9) | 0.0257 (2) | |
F3 | 0.58957 (12) | 0.16422 (6) | 0.41889 (9) | 0.0251 (2) | |
S1 | 0.24900 (4) | 0.13357 (3) | 0.28462 (3) | 0.01547 (9) | |
O1 | 0.42871 (12) | −0.00359 (7) | 0.34900 (10) | 0.0165 (3) | |
O2 | 0.70626 (13) | 0.01825 (8) | 0.36282 (10) | 0.0198 (3) | |
O3 | 0.66769 (14) | 0.03092 (9) | 0.13796 (11) | 0.0284 (3) | |
O4 | 0.5339 (11) | 0.1819 (7) | 0.0551 (7) | 0.0190 (14) | 0.628 (4) |
O5 | 0.2678 (2) | 0.1828 (2) | 0.07323 (19) | 0.0172 (6) | 0.628 (4) |
O4A | 0.539 (2) | 0.1854 (12) | 0.0708 (12) | 0.019 (3)* | 0.372 (4) |
O5A | 0.2605 (5) | 0.1536 (3) | 0.0707 (4) | 0.0127 (12)* | 0.372 (4) |
C1 | 0.53281 (18) | −0.06505 (11) | 0.39486 (15) | 0.0190 (4) | |
H1A | 0.5356 | −0.1035 | 0.3380 | 0.023* | |
H1B | 0.5137 | −0.0969 | 0.4512 | 0.023* | |
C2 | 0.66612 (18) | −0.02073 (11) | 0.44335 (14) | 0.0188 (4) | |
H2A | 0.6586 | 0.0213 | 0.4947 | 0.023* | |
H2B | 0.7370 | −0.0604 | 0.4844 | 0.023* | |
C3 | 0.7602 (2) | −0.03707 (13) | 0.30583 (18) | 0.0346 (5) | |
H3A | 0.6936 | −0.0811 | 0.2725 | 0.041* | |
H3B | 0.8437 | −0.0628 | 0.3566 | 0.041* | |
C4 | 0.7914 (2) | 0.00843 (13) | 0.22006 (17) | 0.0302 (5) | |
H4A | 0.8454 | 0.0581 | 0.2511 | 0.036* | |
H4B | 0.8448 | −0.0268 | 0.1896 | 0.036* | |
C5 | 0.6710 (4) | 0.0670 (2) | 0.0412 (3) | 0.0265 (8) | 0.628 (4) |
H5A | 0.5954 | 0.0453 | −0.0219 | 0.032* | 0.628 (4) |
H5B | 0.7572 | 0.0528 | 0.0323 | 0.032* | 0.628 (4) |
C6 | 0.6587 (4) | 0.1585 (2) | 0.0466 (3) | 0.0277 (9) | 0.628 (4) |
H6A | 0.7345 | 0.1798 | 0.1099 | 0.033* | 0.628 (4) |
H6B | 0.6655 | 0.1835 | −0.0192 | 0.033* | 0.628 (4) |
C7 | 0.4181 (3) | 0.1653 (2) | −0.0228 (3) | 0.0260 (8) | 0.628 (4) |
H7A | 0.3984 | 0.1061 | −0.0207 | 0.031* | 0.628 (4) |
H7B | 0.4267 | 0.1769 | −0.0932 | 0.031* | 0.628 (4) |
C8 | 0.3024 (3) | 0.2133 (2) | −0.0155 (2) | 0.0224 (8) | 0.628 (4) |
H8A | 0.3275 | 0.2720 | −0.0038 | 0.027* | 0.628 (4) |
H8B | 0.2233 | 0.2083 | −0.0839 | 0.027* | 0.628 (4) |
C5A | 0.7154 (6) | 0.0916 (4) | 0.0729 (5) | 0.0223 (15)* | 0.372 (4) |
H5A1 | 0.7726 | 0.1347 | 0.1203 | 0.027* | 0.372 (4) |
H5A2 | 0.7683 | 0.0634 | 0.0352 | 0.027* | 0.372 (4) |
C6A | 0.5889 (6) | 0.1278 (3) | −0.0065 (4) | 0.0203 (13)* | 0.372 (4) |
H6A1 | 0.5211 | 0.0849 | −0.0420 | 0.024* | 0.372 (4) |
H6A2 | 0.6077 | 0.1603 | −0.0624 | 0.024* | 0.372 (4) |
C7A | 0.4038 (5) | 0.2161 (4) | −0.0158 (4) | 0.0162 (12)* | 0.372 (4) |
H7A1 | 0.3820 | 0.2711 | 0.0051 | 0.019* | 0.372 (4) |
H7A2 | 0.4150 | 0.2214 | −0.0863 | 0.019* | 0.372 (4) |
C8A | 0.2883 (5) | 0.1585 (3) | −0.0277 (4) | 0.0152 (12)* | 0.372 (4) |
H8A1 | 0.2061 | 0.1779 | −0.0872 | 0.018* | 0.372 (4) |
H8A2 | 0.3109 | 0.1032 | −0.0469 | 0.018* | 0.372 (4) |
C9 | 0.16420 (18) | 0.21539 (12) | 0.08784 (14) | 0.0208 (4) | |
C10 | 0.13817 (18) | 0.19722 (10) | 0.18170 (14) | 0.0164 (4) | |
C11 | 0.21004 (18) | 0.03254 (10) | 0.23083 (14) | 0.0152 (3) | |
C12 | 0.30777 (17) | −0.02899 (10) | 0.27364 (14) | 0.0152 (3) | |
C13 | 0.27822 (18) | −0.10965 (11) | 0.23909 (15) | 0.0190 (4) | |
H13A | 0.3428 | −0.1518 | 0.2696 | 0.023* | |
C14 | 0.15347 (19) | −0.12839 (11) | 0.15946 (15) | 0.0204 (4) | |
H14A | 0.1339 | −0.1834 | 0.1350 | 0.024* | |
C15 | 0.05805 (19) | −0.06777 (11) | 0.11580 (15) | 0.0217 (4) | |
H15A | −0.0265 | −0.0809 | 0.0610 | 0.026* | |
C16 | 0.08635 (18) | 0.01251 (11) | 0.15238 (14) | 0.0188 (4) | |
H16A | 0.0201 | 0.0541 | 0.1233 | 0.023* | |
C17 | 0.0842 (2) | 0.27355 (12) | 0.01557 (15) | 0.0272 (4) | |
H17A | 0.1037 | 0.2879 | −0.0466 | 0.033* | |
C18 | −0.0233 (2) | 0.31053 (12) | 0.03366 (17) | 0.0334 (5) | |
H18A | −0.0781 | 0.3494 | −0.0168 | 0.040* | |
C19 | −0.0514 (2) | 0.29152 (13) | 0.12385 (17) | 0.0344 (5) | |
H19A | −0.1258 | 0.3166 | 0.1356 | 0.041* | |
C20 | 0.0298 (2) | 0.23529 (12) | 0.19802 (15) | 0.0249 (4) | |
H20A | 0.0109 | 0.2227 | 0.2609 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sb1 | 0.01774 (7) | 0.01358 (7) | 0.01508 (7) | −0.00293 (4) | 0.00292 (5) | 0.00103 (4) |
F1 | 0.0265 (6) | 0.0154 (5) | 0.0324 (6) | −0.0008 (4) | 0.0089 (5) | 0.0040 (4) |
F2 | 0.0197 (5) | 0.0232 (6) | 0.0299 (6) | −0.0065 (4) | 0.0039 (5) | 0.0017 (5) |
F3 | 0.0323 (6) | 0.0222 (5) | 0.0158 (5) | −0.0009 (5) | 0.0026 (5) | −0.0022 (4) |
S1 | 0.0172 (2) | 0.0145 (2) | 0.0129 (2) | 0.00118 (16) | 0.00333 (17) | −0.00105 (16) |
O1 | 0.0150 (6) | 0.0139 (6) | 0.0173 (6) | 0.0016 (5) | 0.0021 (5) | 0.0007 (5) |
O2 | 0.0206 (7) | 0.0213 (6) | 0.0188 (6) | 0.0027 (5) | 0.0086 (5) | 0.0035 (5) |
O3 | 0.0331 (8) | 0.0331 (8) | 0.0255 (7) | 0.0118 (6) | 0.0182 (6) | 0.0118 (6) |
O4 | 0.021 (2) | 0.024 (2) | 0.014 (3) | 0.0033 (13) | 0.010 (2) | 0.005 (2) |
O5 | 0.0209 (12) | 0.0147 (15) | 0.0166 (12) | 0.0010 (11) | 0.0075 (9) | 0.0023 (10) |
C1 | 0.0187 (9) | 0.0150 (8) | 0.0211 (9) | 0.0046 (7) | 0.0047 (7) | 0.0041 (7) |
C2 | 0.0190 (9) | 0.0215 (9) | 0.0152 (9) | 0.0037 (7) | 0.0054 (7) | 0.0059 (7) |
C3 | 0.0444 (13) | 0.0345 (12) | 0.0333 (12) | 0.0247 (10) | 0.0243 (11) | 0.0157 (9) |
C4 | 0.0285 (11) | 0.0357 (12) | 0.0331 (12) | 0.0095 (9) | 0.0192 (9) | 0.0072 (9) |
C5 | 0.036 (2) | 0.0278 (19) | 0.0234 (18) | 0.0040 (17) | 0.0206 (17) | 0.0049 (16) |
C6 | 0.0308 (19) | 0.0293 (18) | 0.0321 (19) | 0.0020 (14) | 0.0224 (16) | 0.0089 (14) |
C7 | 0.0273 (18) | 0.033 (2) | 0.0185 (16) | −0.0010 (14) | 0.0091 (14) | −0.0011 (13) |
C8 | 0.0246 (17) | 0.0277 (19) | 0.0142 (14) | 0.0004 (13) | 0.0062 (12) | 0.0085 (12) |
C9 | 0.0163 (9) | 0.0258 (10) | 0.0172 (9) | −0.0047 (7) | 0.0024 (7) | −0.0010 (7) |
C10 | 0.0188 (9) | 0.0129 (8) | 0.0143 (8) | −0.0006 (7) | 0.0021 (7) | −0.0012 (6) |
C11 | 0.0177 (9) | 0.0155 (8) | 0.0142 (8) | −0.0006 (7) | 0.0080 (7) | −0.0014 (6) |
C12 | 0.0155 (8) | 0.0172 (8) | 0.0138 (8) | −0.0007 (7) | 0.0066 (7) | 0.0005 (7) |
C13 | 0.0195 (9) | 0.0165 (9) | 0.0217 (9) | 0.0004 (7) | 0.0084 (7) | −0.0001 (7) |
C14 | 0.0227 (9) | 0.0168 (9) | 0.0231 (10) | −0.0033 (7) | 0.0100 (8) | −0.0047 (7) |
C15 | 0.0191 (9) | 0.0240 (10) | 0.0199 (9) | −0.0038 (7) | 0.0047 (7) | −0.0053 (7) |
C16 | 0.0162 (9) | 0.0200 (9) | 0.0193 (9) | 0.0024 (7) | 0.0055 (7) | −0.0008 (7) |
C17 | 0.0309 (11) | 0.0255 (10) | 0.0164 (9) | −0.0113 (8) | −0.0018 (8) | 0.0024 (8) |
C18 | 0.0412 (13) | 0.0177 (10) | 0.0237 (11) | 0.0050 (9) | −0.0090 (9) | −0.0021 (8) |
C19 | 0.0353 (12) | 0.0309 (11) | 0.0278 (11) | 0.0157 (9) | 0.0007 (9) | −0.0086 (9) |
C20 | 0.0268 (10) | 0.0264 (10) | 0.0188 (9) | 0.0068 (8) | 0.0049 (8) | −0.0050 (8) |
Geometric parameters (Å, º) top
Sb1—F2 | 1.9277 (11) | C7—C8 | 1.486 (5) |
Sb1—F3 | 1.9299 (11) | C7—H7A | 0.9900 |
Sb1—F1 | 1.9418 (11) | C7—H7B | 0.9900 |
S1—C10 | 1.7760 (17) | C8—H8A | 0.9900 |
S1—C11 | 1.7820 (17) | C8—H8B | 0.9900 |
O1—C12 | 1.371 (2) | C5A—C6A | 1.492 (8) |
O1—C1 | 1.450 (2) | C5A—H5A1 | 0.9900 |
O2—C3 | 1.424 (2) | C5A—H5A2 | 0.9900 |
O2—C2 | 1.436 (2) | C6A—H6A1 | 0.9900 |
O3—C4 | 1.414 (2) | C6A—H6A2 | 0.9900 |
O3—C5 | 1.425 (3) | C7A—C8A | 1.503 (7) |
O3—C5A | 1.516 (6) | C7A—H7A1 | 0.9900 |
O4—C7 | 1.313 (11) | C7A—H7A2 | 0.9900 |
O4—C6 | 1.419 (11) | C8A—H8A1 | 0.9900 |
O5—C9 | 1.297 (3) | C8A—H8A2 | 0.9900 |
O5—C8 | 1.444 (4) | C9—C17 | 1.395 (3) |
O4A—C7A | 1.56 (2) | C9—C10 | 1.403 (3) |
O4A—C6A | 1.614 (18) | C10—C20 | 1.390 (3) |
O5A—C8A | 1.444 (7) | C11—C16 | 1.384 (2) |
O5A—C9 | 1.508 (5) | C11—C12 | 1.404 (2) |
C1—C2 | 1.506 (2) | C12—C13 | 1.390 (2) |
C1—H1A | 0.9900 | C13—C14 | 1.393 (3) |
C1—H1B | 0.9900 | C13—H13A | 0.9500 |
C2—H2A | 0.9900 | C14—C15 | 1.381 (3) |
C2—H2B | 0.9900 | C14—H14A | 0.9500 |
C3—C4 | 1.494 (3) | C15—C16 | 1.390 (3) |
C3—H3A | 0.9900 | C15—H15A | 0.9500 |
C3—H3B | 0.9900 | C16—H16A | 0.9500 |
C4—H4A | 0.9900 | C17—C18 | 1.386 (3) |
C4—H4B | 0.9900 | C17—H17A | 0.9500 |
C5—C6 | 1.501 (5) | C18—C19 | 1.371 (3) |
C5—H5A | 0.9900 | C18—H18A | 0.9500 |
C5—H5B | 0.9900 | C19—C20 | 1.390 (3) |
C6—H6A | 0.9900 | C19—H19A | 0.9500 |
C6—H6B | 0.9900 | C20—H20A | 0.9500 |
| | | |
F2—Sb1—F3 | 88.00 (5) | C6A—C5A—H5A1 | 110.7 |
F2—Sb1—F1 | 88.83 (5) | O3—C5A—H5A1 | 110.7 |
F3—Sb1—F1 | 87.01 (5) | C6A—C5A—H5A2 | 110.7 |
C10—S1—C11 | 103.83 (8) | O3—C5A—H5A2 | 110.7 |
C12—O1—C1 | 117.65 (13) | H5A1—C5A—H5A2 | 108.8 |
C3—O2—C2 | 113.67 (14) | C5A—C6A—O4A | 101.3 (8) |
C4—O3—C5 | 118.8 (2) | C5A—C6A—H6A1 | 111.5 |
C4—O3—C5A | 101.6 (3) | O4A—C6A—H6A1 | 111.5 |
C5—O3—C5A | 25.1 (2) | C5A—C6A—H6A2 | 111.5 |
C7—O4—C6 | 120.8 (7) | O4A—C6A—H6A2 | 111.5 |
C9—O5—C8 | 117.5 (2) | H6A1—C6A—H6A2 | 109.3 |
C7A—O4A—C6A | 98.2 (9) | C8A—C7A—O4A | 111.9 (8) |
C8A—O5A—C9 | 118.2 (4) | C8A—C7A—H7A1 | 109.2 |
O1—C1—C2 | 107.46 (14) | O4A—C7A—H7A1 | 109.2 |
O1—C1—H1A | 110.2 | C8A—C7A—H7A2 | 109.2 |
C2—C1—H1A | 110.2 | O4A—C7A—H7A2 | 109.2 |
O1—C1—H1B | 110.2 | H7A1—C7A—H7A2 | 107.9 |
C2—C1—H1B | 110.2 | O5A—C8A—C7A | 111.5 (4) |
H1A—C1—H1B | 108.5 | O5A—C8A—H8A1 | 109.3 |
O2—C2—C1 | 112.33 (14) | C7A—C8A—H8A1 | 109.3 |
O2—C2—H2A | 109.1 | O5A—C8A—H8A2 | 109.3 |
C1—C2—H2A | 109.1 | C7A—C8A—H8A2 | 109.3 |
O2—C2—H2B | 109.1 | H8A1—C8A—H8A2 | 108.0 |
C1—C2—H2B | 109.1 | O5—C9—C17 | 120.7 (2) |
H2A—C2—H2B | 107.9 | O5—C9—C10 | 119.87 (19) |
O2—C3—C4 | 109.56 (16) | C17—C9—C10 | 119.22 (18) |
O2—C3—H3A | 109.8 | O5—C9—O5A | 17.72 (19) |
C4—C3—H3A | 109.8 | C17—C9—O5A | 128.6 (2) |
O2—C3—H3B | 109.8 | C10—C9—O5A | 110.9 (2) |
C4—C3—H3B | 109.8 | C20—C10—C9 | 119.06 (16) |
H3A—C3—H3B | 108.2 | C20—C10—S1 | 119.51 (14) |
O3—C4—C3 | 108.40 (17) | C9—C10—S1 | 121.22 (14) |
O3—C4—H4A | 110.0 | C16—C11—C12 | 119.54 (16) |
C3—C4—H4A | 110.0 | C16—C11—S1 | 122.50 (13) |
O3—C4—H4B | 110.0 | C12—C11—S1 | 117.91 (13) |
C3—C4—H4B | 110.0 | O1—C12—C13 | 124.37 (15) |
H4A—C4—H4B | 108.4 | O1—C12—C11 | 115.81 (15) |
O3—C5—C6 | 109.6 (3) | C13—C12—C11 | 119.82 (16) |
O3—C5—H5A | 109.7 | C12—C13—C14 | 119.70 (16) |
C6—C5—H5A | 109.7 | C12—C13—H13A | 120.2 |
O3—C5—H5B | 109.7 | C14—C13—H13A | 120.2 |
C6—C5—H5B | 109.7 | C15—C14—C13 | 120.60 (17) |
H5A—C5—H5B | 108.2 | C15—C14—H14A | 119.7 |
O4—C6—C5 | 111.7 (5) | C13—C14—H14A | 119.7 |
O4—C6—H6A | 109.3 | C14—C15—C16 | 119.65 (17) |
C5—C6—H6A | 109.3 | C14—C15—H15A | 120.2 |
O4—C6—H6B | 109.3 | C16—C15—H15A | 120.2 |
C5—C6—H6B | 109.3 | C11—C16—C15 | 120.65 (17) |
H6A—C6—H6B | 107.9 | C11—C16—H16A | 119.7 |
O4—C7—C8 | 113.4 (5) | C15—C16—H16A | 119.7 |
O4—C7—H7A | 108.9 | C18—C17—C9 | 120.52 (19) |
C8—C7—H7A | 108.9 | C18—C17—H17A | 119.7 |
O4—C7—H7B | 108.9 | C9—C17—H17A | 119.7 |
C8—C7—H7B | 108.9 | C19—C18—C17 | 120.50 (19) |
H7A—C7—H7B | 107.7 | C19—C18—H18A | 119.7 |
O5—C8—C7 | 109.4 (3) | C17—C18—H18A | 119.7 |
O5—C8—H8A | 109.8 | C18—C19—C20 | 119.5 (2) |
C7—C8—H8A | 109.8 | C18—C19—H19A | 120.2 |
O5—C8—H8B | 109.8 | C20—C19—H19A | 120.2 |
C7—C8—H8B | 109.8 | C10—C20—C19 | 121.11 (19) |
H8A—C8—H8B | 108.2 | C10—C20—H20A | 119.4 |
C6A—C5A—O3 | 105.1 (5) | C19—C20—H20A | 119.4 |
| | | |
O1—C1—C2—O2 | −66.91 (18) | O4—C7—C8—O5 | −72.4 (6) |
C1—C2—O2—C3 | −77.18 (19) | C7—C8—O5—C9 | −176.7 (3) |
C2—O2—C3—C4 | 176.81 (16) | C8—O5—C9—C10 | −170.4 (2) |
O2—C3—C4—O3 | −70.5 (2) | O5—C9—C10—S1 | 2.8 (3) |
C3—C4—O3—C5 | −173.0 (2) | C9—C10—S1—C11 | −76.52 (16) |
C4—O3—C5—C6 | −99.1 (3) | C10—S1—C11—C12 | 158.81 (14) |
O3—C5—C6—O4 | −61.7 (6) | S1—C11—C12—O1 | −4.0 (2) |
C5—C6—O4—C7 | −63.3 (9) | C11—C12—O1—C1 | −179.65 (15) |
C6—O4—C7—C8 | −163.8 (6) | C12—O1—C1—C2 | 160.99 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···F1i | 0.99 | 2.45 | 3.368 (2) | 155 |
C13—H13A···F1i | 0.95 | 2.40 | 3.244 (2) | 147 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |