The absolute configuration of the title compound [systematic name: 5-hydroxy-8-(1-hydroxyisopropyl)-3,11-dimethyl-7-oxaspiro[5.5]undec-3-en-2-one], C15H24O4, has been determined using Cu Kα data at 100 K. The configurations at its four asymmetric C centers are 1R, 2S, 7R and 10S. There are two independent molecules in the asymmetric unit, and they form hydrogen-bonded chains in the [100] direction using only the OH groups.
Supporting information
CCDC reference: 647204
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.033
- wR factor = 0.087
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 66.18 Deg.
| Author Response: This was the physical limit of the diffractometer.
The structure had already been determined to theta=32.6 deg. (MoK\a). Cu
radiation was necessary here for maximum anomalous scattering, and
collection of many Friedel pairs was more important than high resolution.
|
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 40 Ang.
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 66.20
From the CIF: _reflns_number_total 4578
Count of symmetry unique reflns 2650
Completeness (_total/calc) 172.75%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1928
Fraction of Friedel pairs measured 0.728
Are heavy atom types Z>Si present no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1A = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1B = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2A = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2B = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7A = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7B = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10A = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10B = . S
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
9 ALERT level G = General alerts; check
9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: XPREP (Sheldrick, 2003); 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.
(1
R,2S,7
R,10S)-5-hydroxy-8-(1-hydroxyisopropyl)-3,11-dimethyl-
7-oxaspiro[5.5]undec-3-en-2-one
top
Crystal data top
C15H24O4 | F(000) = 584 |
Mr = 268.34 | Dx = 1.243 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 13509 reflections |
a = 10.3142 (4) Å | θ = 3.7–66.2° |
b = 11.9229 (4) Å | µ = 0.72 mm−1 |
c = 12.2124 (4) Å | T = 100 K |
β = 107.223 (2)° | Fragment, colorless |
V = 1434.48 (9) Å3 | 0.38 × 0.35 × 0.32 mm |
Z = 4 | |
Data collection top
Bruker Kappa APEXII CCD area-detector diffractometer | 4578 independent reflections |
Radiation source: fine-focus sealed tube | 4573 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
φ and ω scans | θmax = 66.2°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −12→12 |
Tmin = 0.772, Tmax = 0.802 | k = −14→14 |
13509 measured reflections | l = −13→14 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0552P)2 + 0.437P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.087 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.37 e Å−3 |
4578 reflections | Δρmin = −0.17 e Å−3 |
365 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0011 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 2065 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.08 (12) |
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 | |
O1A | 0.37515 (14) | 0.53484 (12) | 0.36518 (10) | 0.0280 (3) | |
H1A | 0.458 (3) | 0.556 (2) | 0.400 (2) | 0.042* | |
O2A | 0.18743 (13) | 0.42089 (12) | −0.07966 (11) | 0.0322 (3) | |
O3A | 0.57468 (11) | 0.52825 (10) | 0.23064 (9) | 0.0193 (3) | |
O4A | 0.82814 (13) | 0.60106 (11) | 0.34936 (10) | 0.0229 (3) | |
H4A | 0.904 (3) | 0.580 (2) | 0.384 (2) | 0.034* | |
C1A | 0.42994 (17) | 0.53526 (16) | 0.17974 (14) | 0.0211 (4) | |
C2A | 0.37714 (18) | 0.47032 (16) | 0.26744 (15) | 0.0236 (4) | |
H2A | 0.4423 | 0.4073 | 0.2964 | 0.028* | |
C3A | 0.24010 (18) | 0.41802 (15) | 0.21931 (16) | 0.0243 (4) | |
H3A | 0.1920 | 0.3994 | 0.2722 | 0.029* | |
C4A | 0.17902 (19) | 0.39503 (15) | 0.10895 (16) | 0.0250 (4) | |
C5A | 0.24537 (19) | 0.42989 (15) | 0.02272 (15) | 0.0243 (4) | |
C6A | 0.39038 (18) | 0.47051 (16) | 0.06518 (14) | 0.0228 (4) | |
H61A | 0.4077 | 0.5196 | 0.0057 | 0.027* | |
H62A | 0.4511 | 0.4047 | 0.0736 | 0.027* | |
C7A | 0.38676 (18) | 0.65993 (16) | 0.16741 (15) | 0.0245 (4) | |
H7A | 0.4082 | 0.6911 | 0.2468 | 0.029* | |
C8A | 0.47183 (19) | 0.72584 (15) | 0.10632 (15) | 0.0257 (4) | |
H81A | 0.4478 | 0.7017 | 0.0252 | 0.031* | |
H82A | 0.4504 | 0.8067 | 0.1076 | 0.031* | |
C9A | 0.62338 (19) | 0.70849 (15) | 0.16231 (15) | 0.0258 (4) | |
H91A | 0.6750 | 0.7464 | 0.1163 | 0.031* | |
H92A | 0.6505 | 0.7422 | 0.2399 | 0.031* | |
C10A | 0.65676 (17) | 0.58440 (14) | 0.17090 (14) | 0.0193 (4) | |
H10A | 0.6350 | 0.5528 | 0.0916 | 0.023* | |
C11A | 0.80390 (17) | 0.55500 (15) | 0.23579 (14) | 0.0202 (4) | |
C12A | 0.90242 (18) | 0.60775 (17) | 0.17930 (15) | 0.0265 (4) | |
H12A | 0.8907 | 0.6894 | 0.1766 | 0.040* | |
H12B | 0.8842 | 0.5786 | 0.1012 | 0.040* | |
H12C | 0.9957 | 0.5892 | 0.2238 | 0.040* | |
C13A | 0.82226 (19) | 0.42787 (16) | 0.24304 (16) | 0.0261 (4) | |
H13A | 0.9165 | 0.4100 | 0.2855 | 0.039* | |
H13B | 0.8007 | 0.3966 | 0.1655 | 0.039* | |
H13C | 0.7613 | 0.3955 | 0.2828 | 0.039* | |
C14A | 0.2359 (2) | 0.68034 (16) | 0.11006 (18) | 0.0300 (4) | |
H14A | 0.2118 | 0.6559 | 0.0299 | 0.045* | |
H14B | 0.2161 | 0.7605 | 0.1130 | 0.045* | |
H14C | 0.1827 | 0.6378 | 0.1504 | 0.045* | |
C15A | 0.04603 (19) | 0.33593 (17) | 0.06709 (17) | 0.0296 (4) | |
H15A | 0.0177 | 0.3103 | 0.1328 | 0.044* | |
H15B | 0.0553 | 0.2712 | 0.0205 | 0.044* | |
H15C | −0.0223 | 0.3874 | 0.0205 | 0.044* | |
O1B | 0.64494 (13) | 0.60681 (12) | 0.46888 (11) | 0.0271 (3) | |
H1B | 0.699 (3) | 0.602 (2) | 0.425 (2) | 0.041* | |
O2B | 0.76635 (14) | 0.50804 (12) | 0.90985 (11) | 0.0339 (3) | |
O3B | 0.94388 (11) | 0.55635 (10) | 0.59198 (9) | 0.0197 (3) | |
O4B | 1.12071 (13) | 0.52886 (11) | 0.46070 (10) | 0.0244 (3) | |
H4B | 1.187 (3) | 0.535 (2) | 0.437 (2) | 0.037* | |
C1B | 0.82902 (17) | 0.53099 (15) | 0.63331 (14) | 0.0218 (4) | |
C2B | 0.72830 (18) | 0.62646 (15) | 0.58271 (14) | 0.0232 (4) | |
H2B | 0.7835 | 0.6949 | 0.5804 | 0.028* | |
C3B | 0.63344 (19) | 0.65640 (15) | 0.65125 (16) | 0.0247 (4) | |
H3B | 0.5573 | 0.7017 | 0.6142 | 0.030* | |
C4B | 0.64592 (19) | 0.62555 (15) | 0.75885 (16) | 0.0257 (4) | |
C5B | 0.76093 (19) | 0.55310 (16) | 0.81915 (15) | 0.0270 (4) | |
C6B | 0.87516 (18) | 0.54200 (16) | 0.76585 (14) | 0.0236 (4) | |
H61B | 0.9299 | 0.4752 | 0.7989 | 0.028* | |
H62B | 0.9348 | 0.6085 | 0.7873 | 0.028* | |
C7B | 0.77627 (18) | 0.41350 (16) | 0.58971 (14) | 0.0234 (4) | |
H7B | 0.7508 | 0.4166 | 0.5041 | 0.028* | |
C8B | 0.89005 (19) | 0.32811 (15) | 0.62767 (16) | 0.0262 (4) | |
H81B | 0.8567 | 0.2537 | 0.5953 | 0.031* | |
H82B | 0.9185 | 0.3218 | 0.7123 | 0.031* | |
C9B | 1.01156 (18) | 0.36201 (15) | 0.58823 (15) | 0.0244 (4) | |
H91B | 1.0873 | 0.3089 | 0.6198 | 0.029* | |
H92B | 0.9866 | 0.3586 | 0.5035 | 0.029* | |
C10B | 1.05672 (17) | 0.47962 (15) | 0.62812 (14) | 0.0201 (3) | |
H10B | 1.0892 | 0.4795 | 0.7138 | 0.024* | |
C11B | 1.16975 (17) | 0.52799 (16) | 0.58451 (14) | 0.0213 (4) | |
C12B | 1.29663 (19) | 0.45570 (17) | 0.62368 (17) | 0.0291 (4) | |
H12D | 1.2780 | 0.3816 | 0.5877 | 0.044* | |
H12E | 1.3231 | 0.4474 | 0.7072 | 0.044* | |
H12F | 1.3705 | 0.4915 | 0.6013 | 0.044* | |
C13B | 1.20162 (19) | 0.64798 (16) | 0.62810 (16) | 0.0276 (4) | |
H13D | 1.2764 | 0.6775 | 0.6024 | 0.041* | |
H13E | 1.2279 | 0.6484 | 0.7121 | 0.041* | |
H13F | 1.1210 | 0.6950 | 0.5978 | 0.041* | |
C14B | 0.6496 (2) | 0.37501 (16) | 0.61981 (17) | 0.0292 (4) | |
H14D | 0.6228 | 0.3005 | 0.5872 | 0.044* | |
H14E | 0.5755 | 0.4282 | 0.5882 | 0.044* | |
H14F | 0.6694 | 0.3717 | 0.7033 | 0.044* | |
C15B | 0.5517 (2) | 0.65897 (17) | 0.82510 (16) | 0.0276 (4) | |
H15D | 0.4856 | 0.7133 | 0.7806 | 0.041* | |
H15E | 0.6036 | 0.6930 | 0.8979 | 0.041* | |
H15F | 0.5038 | 0.5925 | 0.8403 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0259 (7) | 0.0396 (7) | 0.0207 (6) | −0.0057 (6) | 0.0102 (5) | −0.0065 (6) |
O2A | 0.0261 (7) | 0.0430 (8) | 0.0248 (7) | −0.0010 (6) | 0.0036 (5) | −0.0070 (6) |
O3A | 0.0166 (6) | 0.0236 (6) | 0.0182 (5) | −0.0013 (5) | 0.0059 (5) | 0.0001 (5) |
O4A | 0.0185 (6) | 0.0310 (7) | 0.0174 (6) | −0.0010 (5) | 0.0024 (5) | −0.0005 (5) |
C1A | 0.0149 (8) | 0.0287 (9) | 0.0203 (8) | 0.0004 (7) | 0.0062 (7) | −0.0017 (7) |
C2A | 0.0228 (9) | 0.0263 (8) | 0.0227 (8) | 0.0000 (7) | 0.0081 (7) | −0.0009 (7) |
C3A | 0.0231 (9) | 0.0240 (9) | 0.0277 (9) | 0.0023 (7) | 0.0106 (7) | 0.0026 (7) |
C4A | 0.0216 (9) | 0.0218 (8) | 0.0311 (9) | 0.0036 (7) | 0.0072 (8) | −0.0014 (7) |
C5A | 0.0240 (9) | 0.0237 (8) | 0.0243 (9) | 0.0030 (7) | 0.0057 (7) | −0.0041 (7) |
C6A | 0.0217 (9) | 0.0264 (8) | 0.0214 (8) | 0.0011 (7) | 0.0080 (7) | −0.0030 (7) |
C7A | 0.0250 (10) | 0.0290 (9) | 0.0201 (8) | 0.0028 (8) | 0.0077 (7) | −0.0041 (7) |
C8A | 0.0296 (10) | 0.0238 (9) | 0.0229 (8) | 0.0042 (8) | 0.0066 (8) | −0.0002 (7) |
C9A | 0.0266 (9) | 0.0250 (9) | 0.0256 (9) | −0.0005 (8) | 0.0073 (8) | 0.0021 (8) |
C10A | 0.0194 (8) | 0.0242 (8) | 0.0155 (8) | −0.0034 (7) | 0.0071 (7) | 0.0002 (6) |
C11A | 0.0190 (8) | 0.0254 (9) | 0.0168 (7) | −0.0009 (7) | 0.0060 (7) | −0.0020 (7) |
C12A | 0.0207 (9) | 0.0358 (10) | 0.0233 (9) | −0.0045 (8) | 0.0069 (7) | −0.0008 (8) |
C13A | 0.0208 (9) | 0.0279 (9) | 0.0285 (9) | 0.0023 (8) | 0.0057 (7) | 0.0009 (8) |
C14A | 0.0266 (10) | 0.0286 (10) | 0.0350 (10) | 0.0064 (8) | 0.0094 (8) | 0.0022 (8) |
C15A | 0.0242 (9) | 0.0300 (9) | 0.0361 (10) | −0.0018 (8) | 0.0115 (8) | −0.0059 (8) |
O1B | 0.0238 (6) | 0.0387 (7) | 0.0184 (6) | 0.0055 (6) | 0.0057 (5) | 0.0003 (5) |
O2B | 0.0406 (8) | 0.0432 (8) | 0.0195 (6) | 0.0077 (6) | 0.0114 (6) | 0.0045 (6) |
O3B | 0.0168 (6) | 0.0230 (6) | 0.0200 (6) | 0.0028 (5) | 0.0066 (5) | 0.0025 (5) |
O4B | 0.0218 (6) | 0.0313 (7) | 0.0209 (6) | 0.0000 (5) | 0.0075 (5) | 0.0015 (5) |
C1B | 0.0199 (8) | 0.0274 (9) | 0.0188 (8) | 0.0017 (7) | 0.0069 (7) | 0.0013 (7) |
C2B | 0.0238 (9) | 0.0258 (9) | 0.0204 (8) | 0.0017 (7) | 0.0070 (7) | 0.0006 (7) |
C3B | 0.0232 (9) | 0.0245 (9) | 0.0241 (9) | −0.0001 (7) | 0.0036 (7) | −0.0024 (7) |
C4B | 0.0255 (9) | 0.0267 (9) | 0.0239 (9) | −0.0045 (8) | 0.0059 (7) | −0.0050 (7) |
C5B | 0.0309 (10) | 0.0284 (9) | 0.0210 (9) | 0.0002 (8) | 0.0068 (8) | −0.0028 (7) |
C6B | 0.0248 (9) | 0.0259 (8) | 0.0190 (8) | 0.0040 (7) | 0.0049 (7) | 0.0006 (7) |
C7B | 0.0245 (9) | 0.0289 (9) | 0.0172 (8) | −0.0027 (8) | 0.0070 (7) | 0.0002 (7) |
C8B | 0.0320 (10) | 0.0227 (9) | 0.0253 (9) | −0.0029 (7) | 0.0108 (8) | −0.0010 (7) |
C9B | 0.0257 (9) | 0.0234 (9) | 0.0257 (9) | 0.0025 (7) | 0.0100 (8) | 0.0008 (7) |
C10B | 0.0196 (9) | 0.0222 (8) | 0.0166 (8) | 0.0049 (7) | 0.0023 (7) | 0.0028 (7) |
C11B | 0.0190 (8) | 0.0248 (9) | 0.0187 (8) | 0.0022 (7) | 0.0036 (7) | 0.0025 (7) |
C12B | 0.0215 (9) | 0.0354 (11) | 0.0311 (10) | 0.0033 (8) | 0.0087 (8) | 0.0057 (8) |
C13B | 0.0230 (9) | 0.0292 (9) | 0.0274 (9) | −0.0024 (8) | 0.0023 (8) | 0.0020 (8) |
C14B | 0.0295 (10) | 0.0297 (10) | 0.0298 (10) | −0.0053 (8) | 0.0111 (8) | −0.0010 (8) |
C15B | 0.0306 (10) | 0.0303 (9) | 0.0228 (9) | −0.0010 (8) | 0.0093 (8) | −0.0038 (7) |
Geometric parameters (Å, º) top
O1A—C2A | 1.425 (2) | O1B—C2B | 1.421 (2) |
O1A—H1A | 0.87 (3) | O1B—H1B | 0.89 (3) |
O2A—C5A | 1.220 (2) | O2B—C5B | 1.217 (2) |
O3A—C10A | 1.4363 (19) | O3B—C10B | 1.443 (2) |
O3A—C1A | 1.440 (2) | O3B—C1B | 1.450 (2) |
O4A—C11A | 1.443 (2) | O4B—C11B | 1.445 (2) |
O4A—H4A | 0.81 (3) | O4B—H4B | 0.82 (3) |
C1A—C6A | 1.543 (2) | C1B—C7B | 1.540 (2) |
C1A—C2A | 1.546 (2) | C1B—C2B | 1.542 (2) |
C1A—C7A | 1.546 (3) | C1B—C6B | 1.552 (2) |
C2A—C3A | 1.497 (3) | C2B—C3B | 1.507 (2) |
C2A—H2A | 1.0000 | C2B—H2B | 1.0000 |
C3A—C4A | 1.336 (3) | C3B—C4B | 1.334 (3) |
C3A—H3A | 0.9500 | C3B—H3B | 0.9500 |
C4A—C5A | 1.475 (3) | C4B—C5B | 1.476 (3) |
C4A—C15A | 1.491 (3) | C4B—C15B | 1.491 (3) |
C5A—C6A | 1.510 (3) | C5B—C6B | 1.511 (3) |
C6A—H61A | 0.9900 | C6B—H61B | 0.9900 |
C6A—H62A | 0.9900 | C6B—H62B | 0.9900 |
C7A—C14A | 1.525 (3) | C7B—C8B | 1.519 (3) |
C7A—C8A | 1.527 (3) | C7B—C14B | 1.529 (2) |
C7A—H7A | 1.0000 | C7B—H7B | 1.0000 |
C8A—C9A | 1.523 (3) | C8B—C9B | 1.524 (2) |
C8A—H81A | 0.9900 | C8B—H81B | 0.9900 |
C8A—H82A | 0.9900 | C8B—H82B | 0.9900 |
C9A—C10A | 1.516 (2) | C9B—C10B | 1.512 (2) |
C9A—H91A | 0.9900 | C9B—H91B | 0.9900 |
C9A—H92A | 0.9900 | C9B—H92B | 0.9900 |
C10A—C11A | 1.530 (2) | C10B—C11B | 1.531 (2) |
C10A—H10A | 1.0000 | C10B—H10B | 1.0000 |
C11A—C12A | 1.523 (2) | C11B—C12B | 1.521 (3) |
C11A—C13A | 1.527 (3) | C11B—C13B | 1.528 (3) |
C12A—H12A | 0.9800 | C12B—H12D | 0.9800 |
C12A—H12B | 0.9800 | C12B—H12E | 0.9800 |
C12A—H12C | 0.9800 | C12B—H12F | 0.9800 |
C13A—H13A | 0.9800 | C13B—H13D | 0.9800 |
C13A—H13B | 0.9800 | C13B—H13E | 0.9800 |
C13A—H13C | 0.9800 | C13B—H13F | 0.9800 |
C14A—H14A | 0.9800 | C14B—H14D | 0.9800 |
C14A—H14B | 0.9800 | C14B—H14E | 0.9800 |
C14A—H14C | 0.9800 | C14B—H14F | 0.9800 |
C15A—H15A | 0.9800 | C15B—H15D | 0.9800 |
C15A—H15B | 0.9800 | C15B—H15E | 0.9800 |
C15A—H15C | 0.9800 | C15B—H15F | 0.9800 |
| | | |
C2A—O1A—H1A | 107.6 (16) | C2B—O1B—H1B | 107.3 (16) |
C10A—O3A—C1A | 116.45 (12) | C10B—O3B—C1B | 115.43 (12) |
C11A—O4A—H4A | 104.8 (17) | C11B—O4B—H4B | 107.0 (16) |
O3A—C1A—C6A | 108.93 (13) | O3B—C1B—C7B | 108.10 (13) |
O3A—C1A—C2A | 101.82 (13) | O3B—C1B—C2B | 103.27 (13) |
C6A—C1A—C2A | 108.95 (14) | C7B—C1B—C2B | 113.95 (14) |
O3A—C1A—C7A | 109.26 (14) | O3B—C1B—C6B | 108.40 (13) |
C6A—C1A—C7A | 113.66 (14) | C7B—C1B—C6B | 113.92 (14) |
C2A—C1A—C7A | 113.49 (14) | C2B—C1B—C6B | 108.53 (14) |
O1A—C2A—C3A | 107.92 (14) | O1B—C2B—C3B | 106.16 (14) |
O1A—C2A—C1A | 113.91 (15) | O1B—C2B—C1B | 114.28 (14) |
C3A—C2A—C1A | 114.97 (14) | C3B—C2B—C1B | 115.07 (14) |
O1A—C2A—H2A | 106.5 | O1B—C2B—H2B | 106.9 |
C3A—C2A—H2A | 106.5 | C3B—C2B—H2B | 106.9 |
C1A—C2A—H2A | 106.5 | C1B—C2B—H2B | 106.9 |
C4A—C3A—C2A | 126.15 (16) | C4B—C3B—C2B | 126.37 (17) |
C4A—C3A—H3A | 116.9 | C4B—C3B—H3B | 116.8 |
C2A—C3A—H3A | 116.9 | C2B—C3B—H3B | 116.8 |
C3A—C4A—C5A | 118.84 (17) | C3B—C4B—C5B | 118.81 (17) |
C3A—C4A—C15A | 123.63 (17) | C3B—C4B—C15B | 124.93 (17) |
C5A—C4A—C15A | 117.54 (16) | C5B—C4B—C15B | 116.26 (16) |
O2A—C5A—C4A | 121.11 (17) | O2B—C5B—C4B | 121.72 (17) |
O2A—C5A—C6A | 120.97 (16) | O2B—C5B—C6B | 121.44 (17) |
C4A—C5A—C6A | 117.82 (15) | C4B—C5B—C6B | 116.77 (15) |
C5A—C6A—C1A | 116.15 (14) | C5B—C6B—C1B | 114.79 (14) |
C5A—C6A—H61A | 108.2 | C5B—C6B—H61B | 108.6 |
C1A—C6A—H61A | 108.2 | C1B—C6B—H61B | 108.6 |
C5A—C6A—H62A | 108.2 | C5B—C6B—H62B | 108.6 |
C1A—C6A—H62A | 108.2 | C1B—C6B—H62B | 108.6 |
H61A—C6A—H62A | 107.4 | H61B—C6B—H62B | 107.5 |
C14A—C7A—C8A | 110.45 (15) | C8B—C7B—C14B | 111.31 (15) |
C14A—C7A—C1A | 115.05 (15) | C8B—C7B—C1B | 110.02 (14) |
C8A—C7A—C1A | 110.59 (14) | C14B—C7B—C1B | 115.45 (14) |
C14A—C7A—H7A | 106.8 | C8B—C7B—H7B | 106.5 |
C8A—C7A—H7A | 106.8 | C14B—C7B—H7B | 106.5 |
C1A—C7A—H7A | 106.8 | C1B—C7B—H7B | 106.5 |
C9A—C8A—C7A | 111.87 (15) | C7B—C8B—C9B | 111.04 (15) |
C9A—C8A—H81A | 109.2 | C7B—C8B—H81B | 109.4 |
C7A—C8A—H81A | 109.2 | C9B—C8B—H81B | 109.4 |
C9A—C8A—H82A | 109.2 | C7B—C8B—H82B | 109.4 |
C7A—C8A—H82A | 109.2 | C9B—C8B—H82B | 109.4 |
H81A—C8A—H82A | 107.9 | H81B—C8B—H82B | 108.0 |
C10A—C9A—C8A | 110.21 (15) | C10B—C9B—C8B | 110.36 (15) |
C10A—C9A—H91A | 109.6 | C10B—C9B—H91B | 109.6 |
C8A—C9A—H91A | 109.6 | C8B—C9B—H91B | 109.6 |
C10A—C9A—H92A | 109.6 | C10B—C9B—H92B | 109.6 |
C8A—C9A—H92A | 109.6 | C8B—C9B—H92B | 109.6 |
H91A—C9A—H92A | 108.1 | H91B—C9B—H92B | 108.1 |
O3A—C10A—C9A | 109.52 (13) | O3B—C10B—C9B | 110.23 (13) |
O3A—C10A—C11A | 105.87 (13) | O3B—C10B—C11B | 106.45 (13) |
C9A—C10A—C11A | 115.44 (14) | C9B—C10B—C11B | 115.54 (14) |
O3A—C10A—H10A | 108.6 | O3B—C10B—H10B | 108.1 |
C9A—C10A—H10A | 108.6 | C9B—C10B—H10B | 108.1 |
C11A—C10A—H10A | 108.6 | C11B—C10B—H10B | 108.1 |
O4A—C11A—C12A | 109.22 (14) | O4B—C11B—C12B | 109.58 (14) |
O4A—C11A—C13A | 109.80 (14) | O4B—C11B—C13B | 109.29 (14) |
C12A—C11A—C13A | 110.39 (15) | C12B—C11B—C13B | 110.17 (15) |
O4A—C11A—C10A | 105.88 (13) | O4B—C11B—C10B | 107.46 (13) |
C12A—C11A—C10A | 111.30 (14) | C12B—C11B—C10B | 110.49 (14) |
C13A—C11A—C10A | 110.14 (14) | C13B—C11B—C10B | 109.81 (14) |
C11A—C12A—H12A | 109.5 | C11B—C12B—H12D | 109.5 |
C11A—C12A—H12B | 109.5 | C11B—C12B—H12E | 109.5 |
H12A—C12A—H12B | 109.5 | H12D—C12B—H12E | 109.5 |
C11A—C12A—H12C | 109.5 | C11B—C12B—H12F | 109.5 |
H12A—C12A—H12C | 109.5 | H12D—C12B—H12F | 109.5 |
H12B—C12A—H12C | 109.5 | H12E—C12B—H12F | 109.5 |
C11A—C13A—H13A | 109.5 | C11B—C13B—H13D | 109.5 |
C11A—C13A—H13B | 109.5 | C11B—C13B—H13E | 109.5 |
H13A—C13A—H13B | 109.5 | H13D—C13B—H13E | 109.5 |
C11A—C13A—H13C | 109.5 | C11B—C13B—H13F | 109.5 |
H13A—C13A—H13C | 109.5 | H13D—C13B—H13F | 109.5 |
H13B—C13A—H13C | 109.5 | H13E—C13B—H13F | 109.5 |
C7A—C14A—H14A | 109.5 | C7B—C14B—H14D | 109.5 |
C7A—C14A—H14B | 109.5 | C7B—C14B—H14E | 109.5 |
H14A—C14A—H14B | 109.5 | H14D—C14B—H14E | 109.5 |
C7A—C14A—H14C | 109.5 | C7B—C14B—H14F | 109.5 |
H14A—C14A—H14C | 109.5 | H14D—C14B—H14F | 109.5 |
H14B—C14A—H14C | 109.5 | H14E—C14B—H14F | 109.5 |
C4A—C15A—H15A | 109.5 | C4B—C15B—H15D | 109.5 |
C4A—C15A—H15B | 109.5 | C4B—C15B—H15E | 109.5 |
H15A—C15A—H15B | 109.5 | H15D—C15B—H15E | 109.5 |
C4A—C15A—H15C | 109.5 | C4B—C15B—H15F | 109.5 |
H15A—C15A—H15C | 109.5 | H15D—C15B—H15F | 109.5 |
H15B—C15A—H15C | 109.5 | H15E—C15B—H15F | 109.5 |
| | | |
C10A—O3A—C1A—C6A | 66.74 (18) | C10B—O3B—C1B—C7B | −59.63 (16) |
C10A—O3A—C1A—C2A | −178.27 (12) | C10B—O3B—C1B—C2B | 179.31 (13) |
C10A—O3A—C1A—C7A | −57.96 (16) | C10B—O3B—C1B—C6B | 64.31 (18) |
O3A—C1A—C2A—O1A | 80.80 (17) | O3B—C1B—C2B—O1B | 84.79 (17) |
C6A—C1A—C2A—O1A | −164.22 (14) | C7B—C1B—C2B—O1B | −32.2 (2) |
C7A—C1A—C2A—O1A | −36.5 (2) | C6B—C1B—C2B—O1B | −160.31 (14) |
O3A—C1A—C2A—C3A | −153.91 (15) | O3B—C1B—C2B—C3B | −151.98 (14) |
C6A—C1A—C2A—C3A | −38.9 (2) | C7B—C1B—C2B—C3B | 91.01 (18) |
C7A—C1A—C2A—C3A | 88.81 (18) | C6B—C1B—C2B—C3B | −37.1 (2) |
O1A—C2A—C3A—C4A | 148.41 (18) | O1B—C2B—C3B—C4B | 141.76 (19) |
C1A—C2A—C3A—C4A | 20.1 (3) | C1B—C2B—C3B—C4B | 14.3 (3) |
C2A—C3A—C4A—C5A | −4.4 (3) | C2B—C3B—C4B—C5B | −1.3 (3) |
C2A—C3A—C4A—C15A | 175.84 (18) | C2B—C3B—C4B—C15B | 178.51 (17) |
C3A—C4A—C5A—O2A | −172.57 (17) | C3B—C4B—C5B—O2B | −168.34 (18) |
C15A—C4A—C5A—O2A | 7.2 (3) | C15B—C4B—C5B—O2B | 11.8 (3) |
C3A—C4A—C5A—C6A | 11.0 (2) | C3B—C4B—C5B—C6B | 14.6 (3) |
C15A—C4A—C5A—C6A | −169.16 (16) | C15B—C4B—C5B—C6B | −165.29 (16) |
O2A—C5A—C6A—C1A | 149.58 (17) | O2B—C5B—C6B—C1B | 142.01 (18) |
C4A—C5A—C6A—C1A | −34.0 (2) | C4B—C5B—C6B—C1B | −40.9 (2) |
O3A—C1A—C6A—C5A | 156.99 (14) | O3B—C1B—C6B—C5B | 162.29 (14) |
C2A—C1A—C6A—C5A | 46.7 (2) | C7B—C1B—C6B—C5B | −77.32 (19) |
C7A—C1A—C6A—C5A | −80.94 (19) | C2B—C1B—C6B—C5B | 50.8 (2) |
O3A—C1A—C7A—C14A | 177.70 (14) | O3B—C1B—C7B—C8B | 56.16 (17) |
C6A—C1A—C7A—C14A | 55.8 (2) | C2B—C1B—C7B—C8B | 170.33 (14) |
C2A—C1A—C7A—C14A | −69.44 (19) | C6B—C1B—C7B—C8B | −64.40 (18) |
O3A—C1A—C7A—C8A | 51.71 (18) | O3B—C1B—C7B—C14B | −176.85 (14) |
C6A—C1A—C7A—C8A | −70.18 (18) | C2B—C1B—C7B—C14B | −62.67 (19) |
C2A—C1A—C7A—C8A | 164.57 (14) | C6B—C1B—C7B—C14B | 62.6 (2) |
C14A—C7A—C8A—C9A | 179.31 (15) | C14B—C7B—C8B—C9B | 175.04 (15) |
C1A—C7A—C8A—C9A | −52.16 (19) | C1B—C7B—C8B—C9B | −55.68 (18) |
C7A—C8A—C9A—C10A | 53.89 (19) | C7B—C8B—C9B—C10B | 54.21 (19) |
C1A—O3A—C10A—C9A | 60.10 (17) | C1B—O3B—C10B—C9B | 59.11 (17) |
C1A—O3A—C10A—C11A | −174.82 (13) | C1B—O3B—C10B—C11B | −174.89 (13) |
C8A—C9A—C10A—O3A | −55.19 (18) | C8B—C9B—C10B—O3B | −53.79 (18) |
C8A—C9A—C10A—C11A | −174.53 (13) | C8B—C9B—C10B—C11B | −174.49 (14) |
O3A—C10A—C11A—O4A | −62.64 (16) | O3B—C10B—C11B—O4B | −63.36 (16) |
C9A—C10A—C11A—O4A | 58.69 (18) | C9B—C10B—C11B—O4B | 59.36 (18) |
O3A—C10A—C11A—C12A | 178.79 (13) | O3B—C10B—C11B—C12B | 177.13 (13) |
C9A—C10A—C11A—C12A | −59.88 (19) | C9B—C10B—C11B—C12B | −60.14 (19) |
O3A—C10A—C11A—C13A | 56.02 (17) | O3B—C10B—C11B—C13B | 55.41 (16) |
C9A—C10A—C11A—C13A | 177.35 (15) | C9B—C10B—C11B—C13B | 178.13 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1B | 0.87 (3) | 1.96 (3) | 2.8278 (19) | 177 (2) |
O4A—H4A···O4B | 0.81 (3) | 2.24 (3) | 3.0440 (19) | 173 (2) |
O1B—H1B···O4A | 0.89 (3) | 1.83 (3) | 2.7091 (18) | 172 (2) |
O4B—H4B···O1Ai | 0.82 (3) | 2.36 (3) | 3.1726 (18) | 174 (2) |
Symmetry code: (i) x+1, y, z. |