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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302717X/hg6009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680302717X/hg6009Isup2.hkl
Contains datablock I

CCDC reference: 232134

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.092
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

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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

Computing details top

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-(1R,11S,12R)-12-hydroxy-15-oxobicyclo[9.3.1]pentadecane-1-carboxylate top
Crystal data top
C18H30O4Z = 4
Mr = 310.42F(000) = 680
Triclinic, P1Dx = 1.176 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.3829 (3) ÅCell parameters from 19813 reflections
b = 12.8139 (2) Åθ = 3.0–27.5°
c = 13.2413 (3) ŵ = 0.08 mm1
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 tubeRint = 0.031
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 1616
356 frames via ω–rotation (Δω =1 °) and two times 20 s per frame (four sets at different κ angles) scansk = 1416
19813 measured reflectionsl = 1717
7889 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H 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 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.17 e Å3
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
xyzUiso*/Ueq
O110.31610 (13)1.21384 (12)0.01753 (11)0.0672 (4)
H110.253 (3)1.256 (3)0.001 (2)0.178 (13)*
O120.00535 (12)0.82032 (11)0.10518 (10)0.0527 (4)
O130.11094 (16)0.61005 (15)0.10388 (13)0.0924 (6)
O140.11287 (12)0.76057 (12)0.05073 (12)0.0634 (4)
C110.19924 (16)0.82251 (17)0.09064 (16)0.0467 (5)
C120.23823 (18)0.77288 (19)0.20319 (18)0.0621 (6)
H12A0.28300.84340.22210.075*
H12B0.29300.73920.19420.075*
C130.1390 (2)0.6727 (2)0.30100 (18)0.0734 (7)
H13A0.06750.68640.29060.088*
H13B0.12020.59160.30060.088*
C140.1696 (2)0.6694 (2)0.41431 (19)0.0916 (8)
H14A0.25240.68250.41560.110*
H14B0.11950.58670.46990.110*
C150.1536 (2)0.7625 (2)0.4447 (2)0.0952 (9)
H15A0.18980.76380.50990.114*
H15B0.19750.84430.38540.114*
C160.0233 (2)0.7415 (2)0.46803 (19)0.0823 (7)
H16A0.01450.67390.54000.099*
H16B0.02040.71600.41350.099*
C170.0138 (2)0.8568 (2)0.46545 (19)0.0836 (7)
H17B0.06990.83490.48620.100*
H17C0.05690.88110.52070.100*
C180.0620 (2)0.96923 (19)0.35487 (17)0.0697 (7)
H18A0.05881.03960.36400.084*
H18B0.14570.99110.33370.084*
C190.00521 (17)0.94941 (19)0.26107 (17)0.0606 (6)
H19A0.07540.96440.26510.073*
H19B0.03300.86280.27170.073*
C1100.06917 (17)1.03303 (17)0.14637 (16)0.0519 (5)
H11D0.01591.02990.09210.062*
H11E0.10801.11860.14000.062*
C1110.16486 (16)0.99650 (16)0.12002 (15)0.0413 (5)
H11F0.20860.98570.18250.050*
C1120.25750 (18)1.09322 (17)0.01504 (16)0.0520 (5)
H11G0.21861.09860.05040.062*
C1130.35681 (18)1.05366 (18)0.00849 (18)0.0662 (6)
H11H0.39491.04880.07350.079*
H11I0.41721.11600.05570.079*
C1140.30764 (17)0.92826 (19)0.00073 (18)0.0665 (6)
H11J0.28370.93840.07110.080*
H11K0.37160.90230.00500.080*
C1150.11189 (18)0.87420 (17)0.10565 (14)0.0421 (5)
C1160.13539 (18)0.7176 (2)0.0513 (2)0.0560 (6)
C1170.05015 (19)0.66844 (19)0.09603 (18)0.0676 (7)
H11L0.08540.61020.08100.081*
H11M0.03360.62160.06180.081*
C1180.0599 (2)0.7339 (2)0.2164 (2)0.1006 (9)
H11N0.01870.67390.24700.151*
H11O0.02430.79090.23070.151*
H11P0.14290.77940.24980.151*
O210.18291 (14)1.34917 (13)0.05084 (12)0.0562 (4)
H210.123 (2)1.316 (2)0.079 (2)0.114 (11)*
O220.37875 (13)1.69685 (13)0.38712 (13)0.0745 (5)
O230.60830 (16)1.93550 (14)0.30979 (15)0.1064 (6)
O240.41661 (14)1.89533 (13)0.31653 (13)0.0825 (5)
C210.45901 (17)1.72094 (17)0.22672 (16)0.0485 (5)
C220.56628 (17)1.68799 (18)0.20327 (16)0.0564 (6)
H22A0.53561.60170.15050.068*
H22B0.61841.73960.16820.068*
C230.64224 (18)1.70362 (18)0.30211 (17)0.0624 (6)
H23A0.59041.67890.35260.075*
H23B0.69781.79110.34070.075*
C240.71332 (19)1.6255 (2)0.26831 (18)0.0723 (7)
H24A0.74861.63410.20440.087*
H24B0.77831.65830.32800.087*
C250.6374 (2)1.4880 (2)0.24112 (18)0.0710 (7)
H25A0.68041.44090.20190.085*
H25B0.56371.45900.19280.085*
C260.6067 (2)1.4632 (2)0.34422 (18)0.0798 (7)
H26A0.67771.46930.38070.096*
H26B0.58831.52940.39400.096*
C270.5029 (2)1.3384 (2)0.32768 (19)0.0864 (8)
H27A0.52031.27170.27730.104*
H27B0.49841.33060.39790.104*
C280.3813 (2)1.31992 (19)0.28292 (18)0.0732 (7)
H28A0.32301.23580.27000.088*
H28B0.38561.32630.21210.088*
C290.3352 (2)1.4122 (2)0.35704 (17)0.0703 (7)
H29A0.29321.38000.40900.084*
H29B0.40361.49110.39920.084*
C2100.25151 (17)1.43624 (18)0.29475 (16)0.0571 (6)
H21D0.21651.48410.34740.069*
H21E0.18671.35690.24730.069*
C2110.31571 (16)1.50716 (16)0.22443 (15)0.0436 (5)
H21F0.37711.47860.19770.052*
C2120.23656 (17)1.48028 (17)0.12149 (16)0.0469 (5)
H21G0.17371.50820.14330.056*
C2130.31053 (17)1.54515 (17)0.05244 (15)0.0522 (5)
H21H0.25771.53040.00980.063*
H21I0.36571.50930.02370.063*
C2140.38147 (18)1.68519 (17)0.11792 (16)0.0592 (6)
H21J0.32591.72270.13500.071*
H21K0.43341.72030.07210.071*
C2150.38244 (17)1.64757 (19)0.29031 (19)0.0494 (5)
C2160.5048 (2)1.8619 (2)0.29116 (19)0.0685 (7)
C2170.4509 (2)2.0291 (2)0.3718 (2)0.1005 (9)
H21L0.50632.06480.43970.121*
H21M0.49032.07070.32460.121*
C2180.3429 (2)2.0461 (2)0.3957 (2)0.1201 (10)
H21N0.36422.13350.43570.180*
H21O0.30252.00120.43940.180*
H21P0.29072.01500.32780.180*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0694 (10)0.0434 (10)0.0739 (11)0.0108 (9)0.0124 (9)0.0238 (8)
O120.0417 (9)0.0476 (9)0.0687 (10)0.0144 (7)0.0111 (7)0.0292 (8)
O130.1483 (16)0.0493 (11)0.0833 (12)0.0424 (12)0.0326 (11)0.0317 (10)
O140.0809 (11)0.0496 (9)0.0653 (11)0.0267 (9)0.0184 (9)0.0310 (9)
C110.0430 (13)0.0411 (13)0.0596 (15)0.0182 (11)0.0101 (12)0.0241 (12)
C120.0596 (15)0.0567 (15)0.0850 (18)0.0331 (14)0.0272 (15)0.0356 (14)
C130.0885 (19)0.0685 (17)0.0698 (17)0.0399 (16)0.0260 (16)0.0288 (15)
C140.116 (2)0.095 (2)0.0810 (19)0.0605 (18)0.0463 (17)0.0387 (17)
C150.116 (2)0.104 (2)0.102 (2)0.061 (2)0.0611 (19)0.0658 (19)
C160.088 (2)0.0789 (19)0.0670 (17)0.0339 (16)0.0037 (15)0.0192 (15)
C170.0963 (19)0.088 (2)0.0642 (18)0.0371 (17)0.0035 (15)0.0307 (17)
C180.0832 (17)0.0657 (17)0.0625 (17)0.0256 (14)0.0025 (14)0.0356 (15)
C190.0547 (14)0.0616 (15)0.0728 (17)0.0270 (13)0.0066 (13)0.0326 (14)
C1100.0585 (13)0.0445 (13)0.0570 (15)0.0241 (12)0.0125 (12)0.0231 (12)
C1110.0455 (12)0.0358 (12)0.0418 (12)0.0157 (11)0.0091 (11)0.0171 (11)
C1120.0547 (14)0.0362 (13)0.0575 (15)0.0101 (12)0.0051 (12)0.0220 (12)
C1130.0547 (14)0.0555 (15)0.0732 (16)0.0112 (13)0.0010 (12)0.0242 (13)
C1140.0504 (14)0.0607 (16)0.0873 (18)0.0167 (13)0.0008 (13)0.0366 (14)
C1150.0456 (13)0.0378 (13)0.0376 (12)0.0149 (12)0.0059 (10)0.0135 (11)
C1160.0595 (15)0.0522 (16)0.0656 (17)0.0271 (14)0.0063 (13)0.0301 (15)
C1170.0712 (16)0.0632 (16)0.0765 (18)0.0206 (13)0.0053 (14)0.0460 (15)
C1180.131 (2)0.085 (2)0.081 (2)0.0373 (18)0.0368 (18)0.0406 (17)
O210.0575 (10)0.0393 (10)0.0562 (10)0.0113 (8)0.0044 (8)0.0143 (8)
O220.0815 (11)0.0570 (10)0.0568 (10)0.0163 (9)0.0233 (9)0.0099 (9)
O230.0633 (12)0.0443 (11)0.1637 (18)0.0031 (10)0.0124 (12)0.0155 (11)
O240.0694 (11)0.0391 (10)0.1161 (14)0.0218 (9)0.0096 (10)0.0100 (9)
C210.0466 (13)0.0333 (13)0.0563 (14)0.0115 (11)0.0107 (12)0.0150 (12)
C220.0506 (14)0.0489 (14)0.0645 (15)0.0154 (12)0.0191 (12)0.0249 (12)
C230.0532 (14)0.0517 (14)0.0650 (16)0.0129 (12)0.0054 (13)0.0168 (12)
C240.0567 (15)0.0848 (19)0.0695 (17)0.0335 (15)0.0059 (13)0.0220 (15)
C250.0833 (17)0.0737 (18)0.0676 (17)0.0479 (16)0.0138 (14)0.0253 (15)
C260.0919 (19)0.0839 (19)0.0717 (18)0.0445 (17)0.0018 (15)0.0325 (16)
C270.115 (2)0.084 (2)0.0755 (18)0.0513 (19)0.0065 (17)0.0384 (16)
C280.098 (2)0.0532 (15)0.0648 (16)0.0295 (15)0.0023 (15)0.0238 (14)
C290.0824 (17)0.0709 (17)0.0530 (15)0.0233 (15)0.0080 (14)0.0315 (14)
C2100.0551 (13)0.0539 (14)0.0532 (14)0.0127 (12)0.0132 (12)0.0248 (12)
C2110.0409 (12)0.0360 (13)0.0488 (13)0.0125 (10)0.0108 (11)0.0168 (11)
C2120.0475 (12)0.0326 (13)0.0543 (14)0.0132 (11)0.0054 (12)0.0157 (12)
C2130.0539 (13)0.0447 (14)0.0546 (14)0.0147 (12)0.0061 (11)0.0239 (12)
C2140.0590 (14)0.0454 (14)0.0692 (16)0.0142 (12)0.0104 (13)0.0287 (13)
C2150.0411 (13)0.0467 (15)0.0523 (15)0.0170 (12)0.0101 (12)0.0141 (13)
C2160.0585 (17)0.0479 (17)0.0863 (19)0.0148 (16)0.0096 (15)0.0232 (15)
C2170.101 (2)0.0424 (17)0.130 (2)0.0296 (16)0.0136 (19)0.0081 (16)
C2180.128 (3)0.066 (2)0.150 (3)0.051 (2)0.023 (2)0.0179 (18)
Geometric parameters (Å, º) top
O11—C1121.4266 (19)O21—C2121.438 (2)
O11—H111.10 (3)O21—H210.84 (2)
O12—C1151.2142 (19)O22—C2151.209 (2)
O13—C1161.193 (2)O23—C2161.199 (2)
O14—C1161.329 (2)O24—C2161.324 (2)
O14—C1171.457 (2)O24—C2171.459 (2)
C11—C1161.532 (2)C21—C2161.528 (3)
C11—C1151.529 (2)C21—C2151.527 (2)
C11—C121.544 (2)C21—C221.546 (2)
C11—C1141.550 (2)C21—C2141.546 (2)
C12—C131.531 (3)C22—C231.523 (2)
C12—H12A0.9700C22—H22A0.9700
C12—H12B0.9700C22—H22B0.9700
C13—C141.532 (2)C23—C241.534 (3)
C13—H13A0.9700C23—H23A0.9700
C13—H13B0.9700C23—H23B0.9700
C14—C151.476 (3)C24—C251.515 (3)
C14—H14A0.9700C24—H24A0.9700
C14—H14B0.9700C24—H24B0.9700
C15—C161.539 (3)C25—C261.523 (3)
C15—H15A0.9700C25—H25A0.9700
C15—H15B0.9700C25—H25B0.9700
C16—C171.517 (3)C26—C271.524 (3)
C16—H16A0.9700C26—H26A0.9700
C16—H16B0.9700C26—H26B0.9700
C17—C181.523 (3)C27—C281.518 (3)
C17—H17B0.9700C27—H27A0.9700
C17—H17C0.9700C27—H27B0.9700
C18—C191.528 (2)C28—C291.535 (3)
C18—H18A0.9700C28—H28A0.9700
C18—H18B0.9700C28—H28B0.9700
C19—C1101.522 (2)C29—C2101.525 (2)
C19—H19A0.9700C29—H29A0.9700
C19—H19B0.9700C29—H29B0.9700
C110—C1111.527 (2)C210—C2111.532 (2)
C110—H11D0.9700C210—H21D0.9700
C110—H11E0.9700C210—H21E0.9700
C111—C1151.517 (2)C211—C2151.520 (2)
C111—C1121.541 (2)C211—C2121.531 (2)
C111—H11F0.9800C211—H21F0.9800
C112—C1131.524 (2)C212—C2131.513 (2)
C112—H11G0.9800C212—H21G0.9800
C113—C1141.511 (2)C213—C2141.520 (2)
C113—H11H0.9700C213—H21H0.9700
C113—H11I0.9700C213—H21I0.9700
C114—H11J0.9700C214—H21J0.9700
C114—H11K0.9700C214—H21K0.9700
C117—C1181.477 (3)C217—C2181.454 (3)
C117—H11L0.9700C217—H21L0.9700
C117—H11M0.9700C217—H21M0.9700
C118—H11N0.9600C218—H21N0.9600
C118—H11O0.9600C218—H21O0.9600
C118—H11P0.9600C218—H21P0.9600
C112—O11—H11107.1 (14)C212—O21—H21105.4 (17)
C116—O14—C117116.80 (16)C216—O24—C217116.66 (19)
C116—C11—C115108.78 (15)C216—C21—C215111.90 (17)
C116—C11—C12111.05 (17)C216—C21—C22109.87 (17)
C115—C11—C12107.71 (15)C215—C21—C22108.12 (15)
C116—C11—C114108.51 (16)C216—C21—C214106.93 (15)
C115—C11—C114108.94 (15)C215—C21—C214109.13 (16)
C12—C11—C114111.78 (16)C22—C21—C214110.91 (16)
C13—C12—C11117.22 (16)C23—C22—C21116.78 (16)
C13—C12—H12A108.0C23—C22—H22A108.1
C11—C12—H12A108.0C21—C22—H22A108.1
C13—C12—H12B108.0C23—C22—H22B108.1
C11—C12—H12B108.0C21—C22—H22B108.1
H12A—C12—H12B107.2H22A—C22—H22B107.3
C12—C13—C14114.94 (19)C22—C23—C24112.32 (17)
C12—C13—H13A108.5C22—C23—H23A109.1
C14—C13—H13A108.5C24—C23—H23A109.1
C12—C13—H13B108.5C22—C23—H23B109.1
C14—C13—H13B108.5C24—C23—H23B109.1
H13A—C13—H13B107.5H23A—C23—H23B107.9
C15—C14—C13114.98 (18)C25—C24—C23113.29 (17)
C15—C14—H14A108.5C25—C24—H24A108.9
C13—C14—H14A108.5C23—C24—H24A108.9
C15—C14—H14B108.5C25—C24—H24B108.9
C13—C14—H14B108.5C23—C24—H24B108.9
H14A—C14—H14B107.5H24A—C24—H24B107.7
C14—C15—C16116.0 (2)C24—C25—C26112.12 (18)
C14—C15—H15A108.3C24—C25—H25A109.2
C16—C15—H15A108.3C26—C25—H25A109.2
C14—C15—H15B108.3C24—C25—H25B109.2
C16—C15—H15B108.3C26—C25—H25B109.2
H15A—C15—H15B107.4H25A—C25—H25B107.9
C17—C16—C15113.1 (2)C27—C26—C25116.88 (19)
C17—C16—H16A109.0C27—C26—H26A108.1
C15—C16—H16A109.0C25—C26—H26A108.1
C17—C16—H16B109.0C27—C26—H26B108.1
C15—C16—H16B109.0C25—C26—H26B108.1
H16A—C16—H16B107.8H26A—C26—H26B107.3
C16—C17—C18115.32 (18)C28—C27—C26114.88 (17)
C16—C17—H17B108.4C28—C27—H27A108.5
C18—C17—H17B108.4C26—C27—H27A108.5
C16—C17—H17C108.4C28—C27—H27B108.5
C18—C17—H17C108.4C26—C27—H27B108.5
H17B—C17—H17C107.5H27A—C27—H27B107.5
C17—C18—C19114.72 (18)C27—C28—C29115.6 (2)
C17—C18—H18A108.6C27—C28—H28A108.4
C19—C18—H18A108.6C29—C28—H28A108.4
C17—C18—H18B108.6C27—C28—H28B108.4
C19—C18—H18B108.6C29—C28—H28B108.4
H18A—C18—H18B107.6H28A—C28—H28B107.5
C110—C19—C18114.21 (16)C210—C29—C28114.32 (17)
C110—C19—H19A108.7C210—C29—H29A108.7
C18—C19—H19A108.7C28—C29—H29A108.7
C110—C19—H19B108.7C210—C29—H29B108.7
C18—C19—H19B108.7C28—C29—H29B108.7
H19A—C19—H19B107.6H29A—C29—H29B107.6
C19—C110—C111113.60 (16)C29—C210—C211112.70 (15)
C19—C110—H11D108.8C29—C210—H21D109.1
C111—C110—H11D108.8C211—C210—H21D109.1
C19—C110—H11E108.8C29—C210—H21E109.1
C111—C110—H11E108.8C211—C210—H21E109.1
H11D—C110—H11E107.7H21D—C210—H21E107.8
C115—C111—C110112.73 (15)C215—C211—C210113.15 (16)
C115—C111—C112106.02 (14)C215—C211—C212109.53 (15)
C110—C111—C112114.91 (15)C210—C211—C212115.09 (15)
C115—C111—H11F107.6C215—C211—H21F106.1
C110—C111—H11F107.6C210—C211—H21F106.1
C112—C111—H11F107.6C212—C211—H21F106.1
O11—C112—C113105.41 (16)O21—C212—C213105.46 (16)
O11—C112—C111112.29 (14)O21—C212—C211110.90 (14)
C113—C112—C111108.98 (16)C213—C212—C211110.89 (15)
O11—C112—H11G110.0O21—C212—H21G109.8
C113—C112—H11G110.0C213—C212—H21G109.8
C111—C112—H11G110.0C211—C212—H21G109.8
C114—C113—C112111.13 (16)C212—C213—C214112.36 (16)
C114—C113—H11H109.4C212—C213—H21H109.1
C112—C113—H11H109.4C214—C213—H21H109.1
C114—C113—H11I109.4C212—C213—H21I109.1
C112—C113—H11I109.4C214—C213—H21I109.1
H11H—C113—H11I108.0H21H—C213—H21I107.9
C113—C114—C11115.18 (16)C213—C214—C21114.07 (15)
C113—C114—H11J108.5C213—C214—H21J108.7
C11—C114—H11J108.5C21—C214—H21J108.7
C113—C114—H11K108.5C213—C214—H21K108.7
C11—C114—H11K108.5C21—C214—H21K108.7
H11J—C114—H11K107.5H21J—C214—H21K107.6
O12—C115—C111121.64 (17)O22—C215—C211122.34 (17)
O12—C115—C11121.53 (16)O22—C215—C21122.48 (19)
C111—C115—C11116.83 (16)C211—C215—C21115.11 (18)
O13—C116—O14123.25 (19)O23—C216—O24123.3 (2)
O13—C116—C11124.7 (2)O23—C216—C21123.9 (2)
O14—C116—C11112.04 (19)O24—C216—C21112.6 (2)
O14—C117—C118108.89 (18)C218—C217—O24108.3 (2)
O14—C117—H11L109.9C218—C217—H21L110.0
C118—C117—H11L109.9O24—C217—H21L110.0
O14—C117—H11M109.9C218—C217—H21M110.0
C118—C117—H11M109.9O24—C217—H21M110.0
H11L—C117—H11M108.3H21L—C217—H21M108.4
C117—C118—H11N109.5C217—C218—H21N109.5
C117—C118—H11O109.5C217—C218—H21O109.5
H11N—C118—H11O109.5H21N—C218—H21O109.5
C117—C118—H11P109.5C217—C218—H21P109.5
H11N—C118—H11P109.5H21N—C218—H21P109.5
H11O—C118—H11P109.5H21O—C218—H21P109.5
C116—C11—C12—C1361.8 (2)C216—C21—C22—C2369.0 (2)
C115—C11—C12—C1357.2 (2)C215—C21—C22—C2353.4 (2)
C114—C11—C12—C13176.86 (16)C214—C21—C22—C23172.97 (15)
C11—C12—C13—C14153.02 (17)C21—C22—C23—C24158.60 (16)
C12—C13—C14—C1581.3 (3)C22—C23—C24—C2577.3 (2)
C13—C14—C15—C1669.2 (3)C23—C24—C25—C2674.2 (2)
C14—C15—C16—C17163.1 (2)C24—C25—C26—C27162.53 (19)
C15—C16—C17—C1862.5 (3)C25—C26—C27—C2864.4 (3)
C16—C17—C18—C1963.7 (3)C26—C27—C28—C2962.6 (3)
C17—C18—C19—C110155.08 (18)C27—C28—C29—C210151.78 (17)
C18—C19—C110—C11172.5 (2)C28—C29—C210—C21167.9 (2)
C19—C110—C111—C11569.9 (2)C29—C210—C211—C21581.8 (2)
C19—C110—C111—C112168.48 (15)C29—C210—C211—C212151.22 (17)
C115—C111—C112—O11179.39 (16)C215—C211—C212—O21173.34 (15)
C110—C111—C112—O1155.4 (2)C210—C211—C212—O2157.9 (2)
C115—C111—C112—C11362.99 (18)C215—C211—C212—C21356.51 (19)
C110—C111—C112—C113171.80 (15)C210—C211—C212—C213174.69 (16)
O11—C112—C113—C114177.76 (16)O21—C212—C213—C214175.77 (15)
C111—C112—C113—C11461.5 (2)C211—C212—C213—C21455.7 (2)
C112—C113—C114—C1152.0 (2)C212—C213—C214—C2152.5 (2)
C116—C11—C114—C113161.72 (18)C216—C21—C214—C213169.74 (17)
C115—C11—C114—C11343.4 (2)C215—C21—C214—C21348.5 (2)
C12—C11—C114—C11375.5 (2)C22—C21—C214—C21370.48 (19)
C110—C111—C115—O126.6 (2)C210—C211—C215—O223.6 (3)
C112—C111—C115—O12119.94 (19)C212—C211—C215—O22126.2 (2)
C110—C111—C115—C11173.99 (16)C210—C211—C215—C21173.64 (16)
C112—C111—C115—C1159.5 (2)C212—C211—C215—C2156.5 (2)
C116—C11—C115—O1212.4 (3)C216—C21—C215—O2213.0 (3)
C12—C11—C115—O12108.1 (2)C22—C21—C215—O22108.1 (2)
C114—C11—C115—O12130.47 (18)C214—C21—C215—O22131.1 (2)
C116—C11—C115—C111167.06 (17)C216—C21—C215—C211169.75 (17)
C12—C11—C115—C11172.5 (2)C22—C21—C215—C21169.1 (2)
C114—C11—C115—C11148.9 (2)C214—C21—C215—C21151.6 (2)
C117—O14—C116—O132.9 (3)C217—O24—C216—O231.2 (3)
C117—O14—C116—C11178.87 (15)C217—O24—C216—C21176.08 (18)
C115—C11—C116—O13113.2 (2)C215—C21—C216—O23127.2 (2)
C12—C11—C116—O135.2 (3)C22—C21—C216—O237.1 (3)
C114—C11—C116—O13128.4 (2)C214—C21—C216—O23113.4 (2)
C115—C11—C116—O1468.6 (2)C215—C21—C216—O2458.0 (2)
C12—C11—C116—O14173.05 (16)C22—C21—C216—O24178.12 (17)
C114—C11—C116—O1449.8 (2)C214—C21—C216—O2461.4 (2)
C116—O14—C117—C118166.01 (18)C216—O24—C217—C218178.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H11···O211.10 (3)1.69 (3)2.771 (2)167 (2)
O21—H21···O12i0.84 (2)1.97 (2)2.7650 (19)156 (2)
Symmetry code: (i) x, y+2, z.
 

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