The asymmetric unit of the title compound, C18H30O4, contains two formula molecules, which are described as trans-fused bicyclic systems. The carbonyl group lies on the same side as the carbethoxy function, while the OH group is on the opposite side. The six-membered rings have chair conformations and the conformations of the 12-membered rings are similar in the two molecules.
Supporting information
CCDC reference: 232134
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.092
- Data-to-parameter ratio = 19.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for C15 - C16 = 10.80 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C21 - C216 = 7.39 su
PLAT355_ALERT_3_B Long O-H Bond (0.82A) O11 - H11 = 1.10 Ang.
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.75 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.56 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.46 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O11 - C112 = 5.58 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C18 H30 O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C18 H30 O4
0 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
6 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
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO & SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHETLXL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
Ethyl
rac-(1
R,11S,12
R)-12-hydroxy-15-oxobicyclo[9.3.1]pentadecane-1-carboxylate
top
Crystal data top
C18H30O4 | Z = 4 |
Mr = 310.42 | F(000) = 680 |
Triclinic, P1 | Dx = 1.176 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.3829 (3) Å | Cell parameters from 19813 reflections |
b = 12.8139 (2) Å | θ = 3.0–27.5° |
c = 13.2413 (3) Å | µ = 0.08 mm−1 |
α = 68.0725 (9)° | T = 291 K |
β = 89.2421 (9)° | Plate, colourless |
γ = 65.829 (1)° | 0.50 × 0.15 × 0.03 mm |
V = 1753.78 (7) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 2673 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −16→16 |
356 frames via ω–rotation (Δω =1 °) and two times 20 s per frame
(four sets at different κ angles) scans | k = −14→16 |
19813 measured reflections | l = −17→17 |
7889 independent reflections | |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.86 | w = 1/[σ2(Fo2) + (0.0215P)2] where P = (Fo2 + 2Fc2)/3 |
7889 reflections | (Δ/σ)max < 0.001 |
407 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.17 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 | |
O11 | −0.31610 (13) | 1.21384 (12) | 0.01753 (11) | 0.0672 (4) | |
H11 | −0.253 (3) | 1.256 (3) | −0.001 (2) | 0.178 (13)* | |
O12 | −0.00535 (12) | 0.82032 (11) | 0.10518 (10) | 0.0527 (4) | |
O13 | −0.11094 (16) | 0.61005 (15) | 0.10388 (13) | 0.0924 (6) | |
O14 | −0.11287 (12) | 0.76057 (12) | −0.05073 (12) | 0.0634 (4) | |
C11 | −0.19924 (16) | 0.82251 (17) | 0.09064 (16) | 0.0467 (5) | |
C12 | −0.23823 (18) | 0.77288 (19) | 0.20319 (18) | 0.0621 (6) | |
H12A | −0.2830 | 0.8434 | 0.2221 | 0.075* | |
H12B | −0.2930 | 0.7392 | 0.1942 | 0.075* | |
C13 | −0.1390 (2) | 0.6727 (2) | 0.30100 (18) | 0.0734 (7) | |
H13A | −0.0675 | 0.6864 | 0.2906 | 0.088* | |
H13B | −0.1202 | 0.5916 | 0.3006 | 0.088* | |
C14 | −0.1696 (2) | 0.6694 (2) | 0.41431 (19) | 0.0916 (8) | |
H14A | −0.2524 | 0.6825 | 0.4156 | 0.110* | |
H14B | −0.1195 | 0.5867 | 0.4699 | 0.110* | |
C15 | −0.1536 (2) | 0.7625 (2) | 0.4447 (2) | 0.0952 (9) | |
H15A | −0.1898 | 0.7638 | 0.5099 | 0.114* | |
H15B | −0.1975 | 0.8443 | 0.3854 | 0.114* | |
C16 | −0.0233 (2) | 0.7415 (2) | 0.46803 (19) | 0.0823 (7) | |
H16A | 0.0145 | 0.6739 | 0.5400 | 0.099* | |
H16B | 0.0204 | 0.7160 | 0.4135 | 0.099* | |
C17 | −0.0138 (2) | 0.8568 (2) | 0.46545 (19) | 0.0836 (7) | |
H17B | 0.0699 | 0.8349 | 0.4862 | 0.100* | |
H17C | −0.0569 | 0.8811 | 0.5207 | 0.100* | |
C18 | −0.0620 (2) | 0.96923 (19) | 0.35487 (17) | 0.0697 (7) | |
H18A | −0.0588 | 1.0396 | 0.3640 | 0.084* | |
H18B | −0.1457 | 0.9911 | 0.3337 | 0.084* | |
C19 | 0.00521 (17) | 0.94941 (19) | 0.26107 (17) | 0.0606 (6) | |
H19A | 0.0754 | 0.9644 | 0.2651 | 0.073* | |
H19B | 0.0330 | 0.8628 | 0.2717 | 0.073* | |
C110 | −0.06917 (17) | 1.03303 (17) | 0.14637 (16) | 0.0519 (5) | |
H11D | −0.0159 | 1.0299 | 0.0921 | 0.062* | |
H11E | −0.1080 | 1.1186 | 0.1400 | 0.062* | |
C111 | −0.16486 (16) | 0.99650 (16) | 0.12002 (15) | 0.0413 (5) | |
H11F | −0.2086 | 0.9857 | 0.1825 | 0.050* | |
C112 | −0.25750 (18) | 1.09322 (17) | 0.01504 (16) | 0.0520 (5) | |
H11G | −0.2186 | 1.0986 | −0.0504 | 0.062* | |
C113 | −0.35681 (18) | 1.05366 (18) | 0.00849 (18) | 0.0662 (6) | |
H11H | −0.3949 | 1.0488 | 0.0735 | 0.079* | |
H11I | −0.4172 | 1.1160 | −0.0557 | 0.079* | |
C114 | −0.30764 (17) | 0.92826 (19) | 0.00073 (18) | 0.0665 (6) | |
H11J | −0.2837 | 0.9384 | −0.0711 | 0.080* | |
H11K | −0.3716 | 0.9023 | 0.0050 | 0.080* | |
C115 | −0.11189 (18) | 0.87420 (17) | 0.10565 (14) | 0.0421 (5) | |
C116 | −0.13539 (18) | 0.7176 (2) | 0.0513 (2) | 0.0560 (6) | |
C117 | −0.05015 (19) | 0.66844 (19) | −0.09603 (18) | 0.0676 (7) | |
H11L | −0.0854 | 0.6102 | −0.0810 | 0.081* | |
H11M | 0.0336 | 0.6216 | −0.0618 | 0.081* | |
C118 | −0.0599 (2) | 0.7339 (2) | −0.2164 (2) | 0.1006 (9) | |
H11N | −0.0187 | 0.6739 | −0.2470 | 0.151* | |
H11O | −0.0243 | 0.7909 | −0.2307 | 0.151* | |
H11P | −0.1429 | 0.7794 | −0.2498 | 0.151* | |
O21 | −0.18291 (14) | 1.34917 (13) | −0.05084 (12) | 0.0562 (4) | |
H21 | −0.123 (2) | 1.316 (2) | −0.079 (2) | 0.114 (11)* | |
O22 | −0.37875 (13) | 1.69685 (13) | −0.38712 (13) | 0.0745 (5) | |
O23 | −0.60830 (16) | 1.93550 (14) | −0.30979 (15) | 0.1064 (6) | |
O24 | −0.41661 (14) | 1.89533 (13) | −0.31653 (13) | 0.0825 (5) | |
C21 | −0.45901 (17) | 1.72094 (17) | −0.22672 (16) | 0.0485 (5) | |
C22 | −0.56628 (17) | 1.68799 (18) | −0.20327 (16) | 0.0564 (6) | |
H22A | −0.5356 | 1.6017 | −0.1505 | 0.068* | |
H22B | −0.6184 | 1.7396 | −0.1682 | 0.068* | |
C23 | −0.64224 (18) | 1.70362 (18) | −0.30211 (17) | 0.0624 (6) | |
H23A | −0.5904 | 1.6789 | −0.3526 | 0.075* | |
H23B | −0.6978 | 1.7911 | −0.3407 | 0.075* | |
C24 | −0.71332 (19) | 1.6255 (2) | −0.26831 (18) | 0.0723 (7) | |
H24A | −0.7486 | 1.6341 | −0.2044 | 0.087* | |
H24B | −0.7783 | 1.6583 | −0.3280 | 0.087* | |
C25 | −0.6374 (2) | 1.4880 (2) | −0.24112 (18) | 0.0710 (7) | |
H25A | −0.6804 | 1.4409 | −0.2019 | 0.085* | |
H25B | −0.5637 | 1.4590 | −0.1928 | 0.085* | |
C26 | −0.6067 (2) | 1.4632 (2) | −0.34422 (18) | 0.0798 (7) | |
H26A | −0.6777 | 1.4693 | −0.3807 | 0.096* | |
H26B | −0.5883 | 1.5294 | −0.3940 | 0.096* | |
C27 | −0.5029 (2) | 1.3384 (2) | −0.32768 (19) | 0.0864 (8) | |
H27A | −0.5203 | 1.2717 | −0.2773 | 0.104* | |
H27B | −0.4984 | 1.3306 | −0.3979 | 0.104* | |
C28 | −0.3813 (2) | 1.31992 (19) | −0.28292 (18) | 0.0732 (7) | |
H28A | −0.3230 | 1.2358 | −0.2700 | 0.088* | |
H28B | −0.3856 | 1.3263 | −0.2121 | 0.088* | |
C29 | −0.3352 (2) | 1.4122 (2) | −0.35704 (17) | 0.0703 (7) | |
H29A | −0.2932 | 1.3800 | −0.4090 | 0.084* | |
H29B | −0.4036 | 1.4911 | −0.3992 | 0.084* | |
C210 | −0.25151 (17) | 1.43624 (18) | −0.29475 (16) | 0.0571 (6) | |
H21D | −0.2165 | 1.4841 | −0.3474 | 0.069* | |
H21E | −0.1867 | 1.3569 | −0.2473 | 0.069* | |
C211 | −0.31571 (16) | 1.50716 (16) | −0.22443 (15) | 0.0436 (5) | |
H21F | −0.3771 | 1.4786 | −0.1977 | 0.052* | |
C212 | −0.23656 (17) | 1.48028 (17) | −0.12149 (16) | 0.0469 (5) | |
H21G | −0.1737 | 1.5082 | −0.1433 | 0.056* | |
C213 | −0.31053 (17) | 1.54515 (17) | −0.05244 (15) | 0.0522 (5) | |
H21H | −0.2577 | 1.5304 | 0.0098 | 0.063* | |
H21I | −0.3657 | 1.5093 | −0.0237 | 0.063* | |
C214 | −0.38147 (18) | 1.68519 (17) | −0.11792 (16) | 0.0592 (6) | |
H21J | −0.3259 | 1.7227 | −0.1350 | 0.071* | |
H21K | −0.4334 | 1.7203 | −0.0721 | 0.071* | |
C215 | −0.38244 (17) | 1.64757 (19) | −0.29031 (19) | 0.0494 (5) | |
C216 | −0.5048 (2) | 1.8619 (2) | −0.29116 (19) | 0.0685 (7) | |
C217 | −0.4509 (2) | 2.0291 (2) | −0.3718 (2) | 0.1005 (9) | |
H21L | −0.5063 | 2.0648 | −0.4397 | 0.121* | |
H21M | −0.4903 | 2.0707 | −0.3246 | 0.121* | |
C218 | −0.3429 (2) | 2.0461 (2) | −0.3957 (2) | 0.1201 (10) | |
H21N | −0.3642 | 2.1335 | −0.4357 | 0.180* | |
H21O | −0.3025 | 2.0012 | −0.4394 | 0.180* | |
H21P | −0.2907 | 2.0150 | −0.3278 | 0.180* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O11 | 0.0694 (10) | 0.0434 (10) | 0.0739 (11) | −0.0108 (9) | 0.0124 (9) | −0.0238 (8) |
O12 | 0.0417 (9) | 0.0476 (9) | 0.0687 (10) | −0.0144 (7) | 0.0111 (7) | −0.0292 (8) |
O13 | 0.1483 (16) | 0.0493 (11) | 0.0833 (12) | −0.0424 (12) | 0.0326 (11) | −0.0317 (10) |
O14 | 0.0809 (11) | 0.0496 (9) | 0.0653 (11) | −0.0267 (9) | 0.0184 (9) | −0.0310 (9) |
C11 | 0.0430 (13) | 0.0411 (13) | 0.0596 (15) | −0.0182 (11) | 0.0101 (12) | −0.0241 (12) |
C12 | 0.0596 (15) | 0.0567 (15) | 0.0850 (18) | −0.0331 (14) | 0.0272 (15) | −0.0356 (14) |
C13 | 0.0885 (19) | 0.0685 (17) | 0.0698 (17) | −0.0399 (16) | 0.0260 (16) | −0.0288 (15) |
C14 | 0.116 (2) | 0.095 (2) | 0.0810 (19) | −0.0605 (18) | 0.0463 (17) | −0.0387 (17) |
C15 | 0.116 (2) | 0.104 (2) | 0.102 (2) | −0.061 (2) | 0.0611 (19) | −0.0658 (19) |
C16 | 0.088 (2) | 0.0789 (19) | 0.0670 (17) | −0.0339 (16) | 0.0037 (15) | −0.0192 (15) |
C17 | 0.0963 (19) | 0.088 (2) | 0.0642 (18) | −0.0371 (17) | 0.0035 (15) | −0.0307 (17) |
C18 | 0.0832 (17) | 0.0657 (17) | 0.0625 (17) | −0.0256 (14) | 0.0025 (14) | −0.0356 (15) |
C19 | 0.0547 (14) | 0.0616 (15) | 0.0728 (17) | −0.0270 (13) | 0.0066 (13) | −0.0326 (14) |
C110 | 0.0585 (13) | 0.0445 (13) | 0.0570 (15) | −0.0241 (12) | 0.0125 (12) | −0.0231 (12) |
C111 | 0.0455 (12) | 0.0358 (12) | 0.0418 (12) | −0.0157 (11) | 0.0091 (11) | −0.0171 (11) |
C112 | 0.0547 (14) | 0.0362 (13) | 0.0575 (15) | −0.0101 (12) | 0.0051 (12) | −0.0220 (12) |
C113 | 0.0547 (14) | 0.0555 (15) | 0.0732 (16) | −0.0112 (13) | −0.0010 (12) | −0.0242 (13) |
C114 | 0.0504 (14) | 0.0607 (16) | 0.0873 (18) | −0.0167 (13) | −0.0008 (13) | −0.0366 (14) |
C115 | 0.0456 (13) | 0.0378 (13) | 0.0376 (12) | −0.0149 (12) | 0.0059 (10) | −0.0135 (11) |
C116 | 0.0595 (15) | 0.0522 (16) | 0.0656 (17) | −0.0271 (14) | 0.0063 (13) | −0.0301 (15) |
C117 | 0.0712 (16) | 0.0632 (16) | 0.0765 (18) | −0.0206 (13) | 0.0053 (14) | −0.0460 (15) |
C118 | 0.131 (2) | 0.085 (2) | 0.081 (2) | −0.0373 (18) | 0.0368 (18) | −0.0406 (17) |
O21 | 0.0575 (10) | 0.0393 (10) | 0.0562 (10) | −0.0113 (8) | 0.0044 (8) | −0.0143 (8) |
O22 | 0.0815 (11) | 0.0570 (10) | 0.0568 (10) | −0.0163 (9) | 0.0233 (9) | −0.0099 (9) |
O23 | 0.0633 (12) | 0.0443 (11) | 0.1637 (18) | −0.0031 (10) | 0.0124 (12) | −0.0155 (11) |
O24 | 0.0694 (11) | 0.0391 (10) | 0.1161 (14) | −0.0218 (9) | 0.0096 (10) | −0.0100 (9) |
C21 | 0.0466 (13) | 0.0333 (13) | 0.0563 (14) | −0.0115 (11) | 0.0107 (12) | −0.0150 (12) |
C22 | 0.0506 (14) | 0.0489 (14) | 0.0645 (15) | −0.0154 (12) | 0.0191 (12) | −0.0249 (12) |
C23 | 0.0532 (14) | 0.0517 (14) | 0.0650 (16) | −0.0129 (12) | 0.0054 (13) | −0.0168 (12) |
C24 | 0.0567 (15) | 0.0848 (19) | 0.0695 (17) | −0.0335 (15) | 0.0059 (13) | −0.0220 (15) |
C25 | 0.0833 (17) | 0.0737 (18) | 0.0676 (17) | −0.0479 (16) | 0.0138 (14) | −0.0253 (15) |
C26 | 0.0919 (19) | 0.0839 (19) | 0.0717 (18) | −0.0445 (17) | 0.0018 (15) | −0.0325 (16) |
C27 | 0.115 (2) | 0.084 (2) | 0.0755 (18) | −0.0513 (19) | 0.0065 (17) | −0.0384 (16) |
C28 | 0.098 (2) | 0.0532 (15) | 0.0648 (16) | −0.0295 (15) | −0.0023 (15) | −0.0238 (14) |
C29 | 0.0824 (17) | 0.0709 (17) | 0.0530 (15) | −0.0233 (15) | 0.0080 (14) | −0.0315 (14) |
C210 | 0.0551 (13) | 0.0539 (14) | 0.0532 (14) | −0.0127 (12) | 0.0132 (12) | −0.0248 (12) |
C211 | 0.0409 (12) | 0.0360 (13) | 0.0488 (13) | −0.0125 (10) | 0.0108 (11) | −0.0168 (11) |
C212 | 0.0475 (12) | 0.0326 (13) | 0.0543 (14) | −0.0132 (11) | 0.0054 (12) | −0.0157 (12) |
C213 | 0.0539 (13) | 0.0447 (14) | 0.0546 (14) | −0.0147 (12) | 0.0061 (11) | −0.0239 (12) |
C214 | 0.0590 (14) | 0.0454 (14) | 0.0692 (16) | −0.0142 (12) | 0.0104 (13) | −0.0287 (13) |
C215 | 0.0411 (13) | 0.0467 (15) | 0.0523 (15) | −0.0170 (12) | 0.0101 (12) | −0.0141 (13) |
C216 | 0.0585 (17) | 0.0479 (17) | 0.0863 (19) | −0.0148 (16) | 0.0096 (15) | −0.0232 (15) |
C217 | 0.101 (2) | 0.0424 (17) | 0.130 (2) | −0.0296 (16) | 0.0136 (19) | −0.0081 (16) |
C218 | 0.128 (3) | 0.066 (2) | 0.150 (3) | −0.051 (2) | 0.023 (2) | −0.0179 (18) |
Geometric parameters (Å, º) top
O11—C112 | 1.4266 (19) | O21—C212 | 1.438 (2) |
O11—H11 | 1.10 (3) | O21—H21 | 0.84 (2) |
O12—C115 | 1.2142 (19) | O22—C215 | 1.209 (2) |
O13—C116 | 1.193 (2) | O23—C216 | 1.199 (2) |
O14—C116 | 1.329 (2) | O24—C216 | 1.324 (2) |
O14—C117 | 1.457 (2) | O24—C217 | 1.459 (2) |
C11—C116 | 1.532 (2) | C21—C216 | 1.528 (3) |
C11—C115 | 1.529 (2) | C21—C215 | 1.527 (2) |
C11—C12 | 1.544 (2) | C21—C22 | 1.546 (2) |
C11—C114 | 1.550 (2) | C21—C214 | 1.546 (2) |
C12—C13 | 1.531 (3) | C22—C23 | 1.523 (2) |
C12—H12A | 0.9700 | C22—H22A | 0.9700 |
C12—H12B | 0.9700 | C22—H22B | 0.9700 |
C13—C14 | 1.532 (2) | C23—C24 | 1.534 (3) |
C13—H13A | 0.9700 | C23—H23A | 0.9700 |
C13—H13B | 0.9700 | C23—H23B | 0.9700 |
C14—C15 | 1.476 (3) | C24—C25 | 1.515 (3) |
C14—H14A | 0.9700 | C24—H24A | 0.9700 |
C14—H14B | 0.9700 | C24—H24B | 0.9700 |
C15—C16 | 1.539 (3) | C25—C26 | 1.523 (3) |
C15—H15A | 0.9700 | C25—H25A | 0.9700 |
C15—H15B | 0.9700 | C25—H25B | 0.9700 |
C16—C17 | 1.517 (3) | C26—C27 | 1.524 (3) |
C16—H16A | 0.9700 | C26—H26A | 0.9700 |
C16—H16B | 0.9700 | C26—H26B | 0.9700 |
C17—C18 | 1.523 (3) | C27—C28 | 1.518 (3) |
C17—H17B | 0.9700 | C27—H27A | 0.9700 |
C17—H17C | 0.9700 | C27—H27B | 0.9700 |
C18—C19 | 1.528 (2) | C28—C29 | 1.535 (3) |
C18—H18A | 0.9700 | C28—H28A | 0.9700 |
C18—H18B | 0.9700 | C28—H28B | 0.9700 |
C19—C110 | 1.522 (2) | C29—C210 | 1.525 (2) |
C19—H19A | 0.9700 | C29—H29A | 0.9700 |
C19—H19B | 0.9700 | C29—H29B | 0.9700 |
C110—C111 | 1.527 (2) | C210—C211 | 1.532 (2) |
C110—H11D | 0.9700 | C210—H21D | 0.9700 |
C110—H11E | 0.9700 | C210—H21E | 0.9700 |
C111—C115 | 1.517 (2) | C211—C215 | 1.520 (2) |
C111—C112 | 1.541 (2) | C211—C212 | 1.531 (2) |
C111—H11F | 0.9800 | C211—H21F | 0.9800 |
C112—C113 | 1.524 (2) | C212—C213 | 1.513 (2) |
C112—H11G | 0.9800 | C212—H21G | 0.9800 |
C113—C114 | 1.511 (2) | C213—C214 | 1.520 (2) |
C113—H11H | 0.9700 | C213—H21H | 0.9700 |
C113—H11I | 0.9700 | C213—H21I | 0.9700 |
C114—H11J | 0.9700 | C214—H21J | 0.9700 |
C114—H11K | 0.9700 | C214—H21K | 0.9700 |
C117—C118 | 1.477 (3) | C217—C218 | 1.454 (3) |
C117—H11L | 0.9700 | C217—H21L | 0.9700 |
C117—H11M | 0.9700 | C217—H21M | 0.9700 |
C118—H11N | 0.9600 | C218—H21N | 0.9600 |
C118—H11O | 0.9600 | C218—H21O | 0.9600 |
C118—H11P | 0.9600 | C218—H21P | 0.9600 |
| | | |
C112—O11—H11 | 107.1 (14) | C212—O21—H21 | 105.4 (17) |
C116—O14—C117 | 116.80 (16) | C216—O24—C217 | 116.66 (19) |
C116—C11—C115 | 108.78 (15) | C216—C21—C215 | 111.90 (17) |
C116—C11—C12 | 111.05 (17) | C216—C21—C22 | 109.87 (17) |
C115—C11—C12 | 107.71 (15) | C215—C21—C22 | 108.12 (15) |
C116—C11—C114 | 108.51 (16) | C216—C21—C214 | 106.93 (15) |
C115—C11—C114 | 108.94 (15) | C215—C21—C214 | 109.13 (16) |
C12—C11—C114 | 111.78 (16) | C22—C21—C214 | 110.91 (16) |
C13—C12—C11 | 117.22 (16) | C23—C22—C21 | 116.78 (16) |
C13—C12—H12A | 108.0 | C23—C22—H22A | 108.1 |
C11—C12—H12A | 108.0 | C21—C22—H22A | 108.1 |
C13—C12—H12B | 108.0 | C23—C22—H22B | 108.1 |
C11—C12—H12B | 108.0 | C21—C22—H22B | 108.1 |
H12A—C12—H12B | 107.2 | H22A—C22—H22B | 107.3 |
C12—C13—C14 | 114.94 (19) | C22—C23—C24 | 112.32 (17) |
C12—C13—H13A | 108.5 | C22—C23—H23A | 109.1 |
C14—C13—H13A | 108.5 | C24—C23—H23A | 109.1 |
C12—C13—H13B | 108.5 | C22—C23—H23B | 109.1 |
C14—C13—H13B | 108.5 | C24—C23—H23B | 109.1 |
H13A—C13—H13B | 107.5 | H23A—C23—H23B | 107.9 |
C15—C14—C13 | 114.98 (18) | C25—C24—C23 | 113.29 (17) |
C15—C14—H14A | 108.5 | C25—C24—H24A | 108.9 |
C13—C14—H14A | 108.5 | C23—C24—H24A | 108.9 |
C15—C14—H14B | 108.5 | C25—C24—H24B | 108.9 |
C13—C14—H14B | 108.5 | C23—C24—H24B | 108.9 |
H14A—C14—H14B | 107.5 | H24A—C24—H24B | 107.7 |
C14—C15—C16 | 116.0 (2) | C24—C25—C26 | 112.12 (18) |
C14—C15—H15A | 108.3 | C24—C25—H25A | 109.2 |
C16—C15—H15A | 108.3 | C26—C25—H25A | 109.2 |
C14—C15—H15B | 108.3 | C24—C25—H25B | 109.2 |
C16—C15—H15B | 108.3 | C26—C25—H25B | 109.2 |
H15A—C15—H15B | 107.4 | H25A—C25—H25B | 107.9 |
C17—C16—C15 | 113.1 (2) | C27—C26—C25 | 116.88 (19) |
C17—C16—H16A | 109.0 | C27—C26—H26A | 108.1 |
C15—C16—H16A | 109.0 | C25—C26—H26A | 108.1 |
C17—C16—H16B | 109.0 | C27—C26—H26B | 108.1 |
C15—C16—H16B | 109.0 | C25—C26—H26B | 108.1 |
H16A—C16—H16B | 107.8 | H26A—C26—H26B | 107.3 |
C16—C17—C18 | 115.32 (18) | C28—C27—C26 | 114.88 (17) |
C16—C17—H17B | 108.4 | C28—C27—H27A | 108.5 |
C18—C17—H17B | 108.4 | C26—C27—H27A | 108.5 |
C16—C17—H17C | 108.4 | C28—C27—H27B | 108.5 |
C18—C17—H17C | 108.4 | C26—C27—H27B | 108.5 |
H17B—C17—H17C | 107.5 | H27A—C27—H27B | 107.5 |
C17—C18—C19 | 114.72 (18) | C27—C28—C29 | 115.6 (2) |
C17—C18—H18A | 108.6 | C27—C28—H28A | 108.4 |
C19—C18—H18A | 108.6 | C29—C28—H28A | 108.4 |
C17—C18—H18B | 108.6 | C27—C28—H28B | 108.4 |
C19—C18—H18B | 108.6 | C29—C28—H28B | 108.4 |
H18A—C18—H18B | 107.6 | H28A—C28—H28B | 107.5 |
C110—C19—C18 | 114.21 (16) | C210—C29—C28 | 114.32 (17) |
C110—C19—H19A | 108.7 | C210—C29—H29A | 108.7 |
C18—C19—H19A | 108.7 | C28—C29—H29A | 108.7 |
C110—C19—H19B | 108.7 | C210—C29—H29B | 108.7 |
C18—C19—H19B | 108.7 | C28—C29—H29B | 108.7 |
H19A—C19—H19B | 107.6 | H29A—C29—H29B | 107.6 |
C19—C110—C111 | 113.60 (16) | C29—C210—C211 | 112.70 (15) |
C19—C110—H11D | 108.8 | C29—C210—H21D | 109.1 |
C111—C110—H11D | 108.8 | C211—C210—H21D | 109.1 |
C19—C110—H11E | 108.8 | C29—C210—H21E | 109.1 |
C111—C110—H11E | 108.8 | C211—C210—H21E | 109.1 |
H11D—C110—H11E | 107.7 | H21D—C210—H21E | 107.8 |
C115—C111—C110 | 112.73 (15) | C215—C211—C210 | 113.15 (16) |
C115—C111—C112 | 106.02 (14) | C215—C211—C212 | 109.53 (15) |
C110—C111—C112 | 114.91 (15) | C210—C211—C212 | 115.09 (15) |
C115—C111—H11F | 107.6 | C215—C211—H21F | 106.1 |
C110—C111—H11F | 107.6 | C210—C211—H21F | 106.1 |
C112—C111—H11F | 107.6 | C212—C211—H21F | 106.1 |
O11—C112—C113 | 105.41 (16) | O21—C212—C213 | 105.46 (16) |
O11—C112—C111 | 112.29 (14) | O21—C212—C211 | 110.90 (14) |
C113—C112—C111 | 108.98 (16) | C213—C212—C211 | 110.89 (15) |
O11—C112—H11G | 110.0 | O21—C212—H21G | 109.8 |
C113—C112—H11G | 110.0 | C213—C212—H21G | 109.8 |
C111—C112—H11G | 110.0 | C211—C212—H21G | 109.8 |
C114—C113—C112 | 111.13 (16) | C212—C213—C214 | 112.36 (16) |
C114—C113—H11H | 109.4 | C212—C213—H21H | 109.1 |
C112—C113—H11H | 109.4 | C214—C213—H21H | 109.1 |
C114—C113—H11I | 109.4 | C212—C213—H21I | 109.1 |
C112—C113—H11I | 109.4 | C214—C213—H21I | 109.1 |
H11H—C113—H11I | 108.0 | H21H—C213—H21I | 107.9 |
C113—C114—C11 | 115.18 (16) | C213—C214—C21 | 114.07 (15) |
C113—C114—H11J | 108.5 | C213—C214—H21J | 108.7 |
C11—C114—H11J | 108.5 | C21—C214—H21J | 108.7 |
C113—C114—H11K | 108.5 | C213—C214—H21K | 108.7 |
C11—C114—H11K | 108.5 | C21—C214—H21K | 108.7 |
H11J—C114—H11K | 107.5 | H21J—C214—H21K | 107.6 |
O12—C115—C111 | 121.64 (17) | O22—C215—C211 | 122.34 (17) |
O12—C115—C11 | 121.53 (16) | O22—C215—C21 | 122.48 (19) |
C111—C115—C11 | 116.83 (16) | C211—C215—C21 | 115.11 (18) |
O13—C116—O14 | 123.25 (19) | O23—C216—O24 | 123.3 (2) |
O13—C116—C11 | 124.7 (2) | O23—C216—C21 | 123.9 (2) |
O14—C116—C11 | 112.04 (19) | O24—C216—C21 | 112.6 (2) |
O14—C117—C118 | 108.89 (18) | C218—C217—O24 | 108.3 (2) |
O14—C117—H11L | 109.9 | C218—C217—H21L | 110.0 |
C118—C117—H11L | 109.9 | O24—C217—H21L | 110.0 |
O14—C117—H11M | 109.9 | C218—C217—H21M | 110.0 |
C118—C117—H11M | 109.9 | O24—C217—H21M | 110.0 |
H11L—C117—H11M | 108.3 | H21L—C217—H21M | 108.4 |
C117—C118—H11N | 109.5 | C217—C218—H21N | 109.5 |
C117—C118—H11O | 109.5 | C217—C218—H21O | 109.5 |
H11N—C118—H11O | 109.5 | H21N—C218—H21O | 109.5 |
C117—C118—H11P | 109.5 | C217—C218—H21P | 109.5 |
H11N—C118—H11P | 109.5 | H21N—C218—H21P | 109.5 |
H11O—C118—H11P | 109.5 | H21O—C218—H21P | 109.5 |
| | | |
C116—C11—C12—C13 | 61.8 (2) | C216—C21—C22—C23 | 69.0 (2) |
C115—C11—C12—C13 | −57.2 (2) | C215—C21—C22—C23 | −53.4 (2) |
C114—C11—C12—C13 | −176.86 (16) | C214—C21—C22—C23 | −172.97 (15) |
C11—C12—C13—C14 | 153.02 (17) | C21—C22—C23—C24 | 158.60 (16) |
C12—C13—C14—C15 | −81.3 (3) | C22—C23—C24—C25 | −77.3 (2) |
C13—C14—C15—C16 | −69.2 (3) | C23—C24—C25—C26 | −74.2 (2) |
C14—C15—C16—C17 | 163.1 (2) | C24—C25—C26—C27 | 162.53 (19) |
C15—C16—C17—C18 | −62.5 (3) | C25—C26—C27—C28 | −64.4 (3) |
C16—C17—C18—C19 | −63.7 (3) | C26—C27—C28—C29 | −62.6 (3) |
C17—C18—C19—C110 | 155.08 (18) | C27—C28—C29—C210 | 151.78 (17) |
C18—C19—C110—C111 | −72.5 (2) | C28—C29—C210—C211 | −67.9 (2) |
C19—C110—C111—C115 | −69.9 (2) | C29—C210—C211—C215 | −81.8 (2) |
C19—C110—C111—C112 | 168.48 (15) | C29—C210—C211—C212 | 151.22 (17) |
C115—C111—C112—O11 | 179.39 (16) | C215—C211—C212—O21 | 173.34 (15) |
C110—C111—C112—O11 | −55.4 (2) | C210—C211—C212—O21 | −57.9 (2) |
C115—C111—C112—C113 | 62.99 (18) | C215—C211—C212—C213 | 56.51 (19) |
C110—C111—C112—C113 | −171.80 (15) | C210—C211—C212—C213 | −174.69 (16) |
O11—C112—C113—C114 | 177.76 (16) | O21—C212—C213—C214 | −175.77 (15) |
C111—C112—C113—C114 | −61.5 (2) | C211—C212—C213—C214 | −55.7 (2) |
C112—C113—C114—C11 | 52.0 (2) | C212—C213—C214—C21 | 52.5 (2) |
C116—C11—C114—C113 | −161.72 (18) | C216—C21—C214—C213 | −169.74 (17) |
C115—C11—C114—C113 | −43.4 (2) | C215—C21—C214—C213 | −48.5 (2) |
C12—C11—C114—C113 | 75.5 (2) | C22—C21—C214—C213 | 70.48 (19) |
C110—C111—C115—O12 | −6.6 (2) | C210—C211—C215—O22 | −3.6 (3) |
C112—C111—C115—O12 | 119.94 (19) | C212—C211—C215—O22 | 126.2 (2) |
C110—C111—C115—C11 | 173.99 (16) | C210—C211—C215—C21 | 173.64 (16) |
C112—C111—C115—C11 | −59.5 (2) | C212—C211—C215—C21 | −56.5 (2) |
C116—C11—C115—O12 | −12.4 (3) | C216—C21—C215—O22 | −13.0 (3) |
C12—C11—C115—O12 | 108.1 (2) | C22—C21—C215—O22 | 108.1 (2) |
C114—C11—C115—O12 | −130.47 (18) | C214—C21—C215—O22 | −131.1 (2) |
C116—C11—C115—C111 | 167.06 (17) | C216—C21—C215—C211 | 169.75 (17) |
C12—C11—C115—C111 | −72.5 (2) | C22—C21—C215—C211 | −69.1 (2) |
C114—C11—C115—C111 | 48.9 (2) | C214—C21—C215—C211 | 51.6 (2) |
C117—O14—C116—O13 | −2.9 (3) | C217—O24—C216—O23 | −1.2 (3) |
C117—O14—C116—C11 | 178.87 (15) | C217—O24—C216—C21 | −176.08 (18) |
C115—C11—C116—O13 | 113.2 (2) | C215—C21—C216—O23 | 127.2 (2) |
C12—C11—C116—O13 | −5.2 (3) | C22—C21—C216—O23 | 7.1 (3) |
C114—C11—C116—O13 | −128.4 (2) | C214—C21—C216—O23 | −113.4 (2) |
C115—C11—C116—O14 | −68.6 (2) | C215—C21—C216—O24 | −58.0 (2) |
C12—C11—C116—O14 | 173.05 (16) | C22—C21—C216—O24 | −178.12 (17) |
C114—C11—C116—O14 | 49.8 (2) | C214—C21—C216—O24 | 61.4 (2) |
C116—O14—C117—C118 | 166.01 (18) | C216—O24—C217—C218 | −178.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···O21 | 1.10 (3) | 1.69 (3) | 2.771 (2) | 167 (2) |
O21—H21···O12i | 0.84 (2) | 1.97 (2) | 2.7650 (19) | 156 (2) |
Symmetry code: (i) −x, −y+2, −z. |