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The structures are presented for both diastereomers of the title compound, C15H20O4, produced by base-catalyzed self-condensation of cyclo­hexane-cis-1,2-di­carboxyl­ic anhydride in refluxing triethyl­amine. Equilibration of either diastereomer under the condensation conditions yielded the same 5:3 mixture. In the crystal, one diastereomer, (II), is ordered, while the other, (I), displays both flexional ring disorder and carboxyl disorder; both aggregate as centrosymmetric hydrogen-bonded dimers [for (I), O...O = 2.680 (2) Å; for (II), O...O = 2.635 (4) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008477/fr1276sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008477/fr1276Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008477/fr1276IIsup3.hkl
Contains datablock II

CCDC references: 150858; 150859

Computing details top

For both compounds, data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

(I) (±)-cis-2-(3-Oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl)- cyclohexanecarboxylic acid top
Crystal data top
C15H20O4F(000) = 284
Mr = 264.32Dx = 1.235 Mg m3
Triclinic, P1Melting point = 444–446 K
a = 6.652 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.616 (4) ÅCell parameters from 33 reflections
c = 11.038 (4) Åθ = 3.8–13.3°
α = 66.18 (1)°µ = 0.09 mm1
β = 88.20 (1)°T = 293 K
γ = 85.61 (2)°Rectangular prism, colorless
V = 711.0 (4) Å30.60 × 0.18 × 0.16 mm
Z = 2
Data collection top
Siemens P4
diffractometer
1790 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
2θ/θ scansh = 77
Absorption correction: numerical
XPREP (Sheldrick, 1997)
k = 1111
Tmin = 0.98, Tmax = 0.99l = 013
4844 measured reflections3 standard reflections every 97 reflections
2422 independent reflections intensity decay: variation < 1%
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0272P)2 + 0.1159P]
where P = (Fo2 + 2Fc2)/3
2422 reflections(Δ/σ)max = 0.01
192 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.12 e Å3
Special details top

Experimental. Crystal mounted on glass fiber using epoxy resin

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*/UeqOcc. (<1)
O10.80540 (18)0.56041 (14)0.60286 (13)0.0579 (4)
O20.48334 (16)0.64264 (11)0.60146 (11)0.0407 (3)
O30.4272 (2)0.91003 (14)0.65943 (12)0.0586 (4)
O40.2717 (2)0.93710 (13)0.47315 (12)0.0570 (4)
C10.2882 (2)0.58538 (16)0.64482 (15)0.0359 (4)
C30.6301 (3)0.53716 (18)0.62922 (16)0.0395 (4)
C3A0.5355 (2)0.40492 (17)0.69056 (15)0.0362 (4)
C40.6387 (3)0.26234 (17)0.73623 (17)0.0463 (4)
C50.489 (3)0.1550 (14)0.7665 (14)0.061 (3)0.351 (11)
C60.3114 (15)0.1823 (7)0.8462 (14)0.067 (3)0.351 (11)
C5'0.4905 (13)0.1563 (8)0.8223 (7)0.0594 (15)0.649 (11)
C6'0.2806 (6)0.1866 (4)0.7606 (8)0.0654 (15)0.649 (11)
C70.1887 (3)0.32496 (18)0.7541 (2)0.0552 (5)
C7A0.3382 (2)0.43209 (16)0.69956 (15)0.0367 (4)
C80.1894 (2)0.64056 (16)0.74287 (15)0.0355 (4)
C90.1195 (2)0.79612 (16)0.67575 (16)0.0390 (4)
C100.0184 (3)0.84559 (19)0.77873 (18)0.0512 (5)
C110.1440 (3)0.80718 (18)0.90404 (17)0.0512 (5)
C120.2033 (3)0.65251 (18)0.96661 (17)0.0504 (5)
C130.3154 (3)0.60468 (17)0.86779 (16)0.0430 (4)
C140.2863 (3)0.88605 (16)0.60161 (16)0.0410 (4)
H10.20020.61210.56760.043*
H30.50590.95790.60450.088*0.31 (3)
H40.36900.98210.44010.086*0.69 (3)
H4A0.73030.25780.66780.056*0.351 (11)
H4B0.71740.24360.81490.056*0.351 (11)
H4A'0.75790.25650.78640.056*0.649 (11)
H4B'0.67980.24310.66090.056*0.649 (11)
H5A0.55500.06460.81670.073*0.351 (11)
H5B0.44040.15560.68450.073*0.351 (11)
H6A0.36010.18930.92510.080*0.351 (11)
H6B0.22350.10680.87350.080*0.351 (11)
H5'A0.54210.06450.83300.071*0.649 (11)
H5'B0.48130.15820.90940.071*0.649 (11)
H6'A0.28970.18830.67200.078*0.649 (11)
H6'B0.19480.11400.81310.078*0.649 (11)
H7A0.12170.31380.68260.066*0.351 (11)
H7B0.08750.35190.80590.066*0.351 (11)
H7A'0.06960.35260.70010.066*0.649 (11)
H7B'0.15030.31570.84190.066*0.649 (11)
H80.06590.59200.77310.043*
H90.01610.80580.61070.047*
H10A0.00670.94510.73770.061*
H10B0.11090.80590.80360.061*
H11A0.26470.85780.88200.061*
H11B0.06670.83340.96730.061*
H12A0.08310.60230.99720.061*
H12B0.28890.63191.04280.061*
H13A0.34600.50560.90920.052*
H13B0.44180.64850.84350.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0404 (8)0.0617 (9)0.0710 (9)0.0131 (6)0.0074 (6)0.0250 (7)
O20.0421 (6)0.0362 (6)0.0420 (6)0.0092 (5)0.0084 (5)0.0133 (5)
O30.0761 (9)0.0606 (9)0.0415 (7)0.0308 (7)0.0040 (7)0.0188 (6)
O40.0671 (9)0.0560 (8)0.0349 (7)0.0091 (7)0.0014 (6)0.0038 (6)
C10.0362 (9)0.0386 (9)0.0336 (8)0.0070 (7)0.0013 (7)0.0148 (7)
C30.0400 (10)0.0465 (10)0.0358 (9)0.0072 (8)0.0022 (7)0.0201 (8)
C3A0.0412 (10)0.0385 (9)0.0330 (8)0.0056 (7)0.0018 (7)0.0183 (7)
C40.0509 (11)0.0455 (11)0.0441 (10)0.0008 (9)0.0005 (8)0.0203 (9)
C50.080 (6)0.037 (4)0.069 (8)0.005 (3)0.014 (7)0.027 (6)
C60.076 (6)0.040 (4)0.086 (7)0.022 (3)0.033 (5)0.025 (4)
C5'0.072 (3)0.036 (2)0.065 (4)0.0037 (18)0.000 (4)0.015 (3)
C6'0.067 (3)0.0391 (19)0.093 (4)0.0160 (16)0.004 (2)0.027 (2)
C70.0501 (11)0.0438 (11)0.0762 (14)0.0140 (9)0.0143 (10)0.0281 (10)
C7A0.0423 (10)0.0372 (9)0.0361 (9)0.0091 (7)0.0037 (7)0.0194 (7)
C80.0384 (9)0.0326 (9)0.0348 (9)0.0079 (7)0.0038 (7)0.0122 (7)
C90.0413 (9)0.0373 (9)0.0364 (9)0.0009 (7)0.0039 (7)0.0128 (7)
C100.0579 (12)0.0431 (10)0.0506 (11)0.0040 (9)0.0055 (9)0.0185 (9)
C110.0699 (13)0.0437 (11)0.0428 (10)0.0041 (9)0.0098 (9)0.0209 (9)
C120.0709 (13)0.0450 (11)0.0347 (9)0.0040 (9)0.0028 (9)0.0154 (8)
C130.0549 (11)0.0362 (9)0.0361 (9)0.0010 (8)0.0024 (8)0.0132 (7)
C140.0569 (11)0.0282 (9)0.0351 (9)0.0008 (8)0.0020 (8)0.0100 (7)
Geometric parameters (Å, º) top
O1—C31.212 (2)C4—H4A0.9700
O2—C31.369 (2)C4—H4B0.9700
O2—C11.4596 (19)C4—H4A'0.9650
O3—C141.248 (2)C4—H4B'0.9605
O4—C141.301 (2)C5—H5A0.9700
C1—C7A1.503 (2)C5—H5B0.9700
C1—C81.535 (2)C6—H6A0.9700
C3—C3A1.472 (2)C6—H6B0.9700
C3A—C7A1.331 (2)C5'—H5'A0.9700
C3A—C41.504 (2)C5'—H5'B0.9700
C4—C51.497 (15)C6'—H6'A0.9700
C4—C5'1.545 (8)C6'—H6'B0.9700
C5—C61.533 (19)C7—H7A0.9700
C6—C71.617 (10)C7—H7B0.9700
C5'—C6'1.527 (11)C7—H7A'0.9601
C6'—C71.523 (5)C7—H7B'0.9626
C7—C7A1.492 (2)C8—H80.9800
C8—C131.532 (2)C9—H90.9800
C8—C91.552 (2)C10—H10A0.9700
C9—C141.512 (2)C10—H10B0.9700
C9—C101.549 (2)C11—H11A0.9700
C10—C111.530 (3)C11—H11B0.9700
C11—C121.527 (3)C12—H12A0.9700
C12—C131.530 (2)C12—H12B0.9700
O3—H30.8200C13—H13A0.9700
O4—H40.8200C13—H13B0.9700
C1—H10.9800
C3—O2—C1109.39 (12)C6—C5—H5B109.5
O2—C1—C7A103.45 (12)H5A—C5—H5B108.1
O2—C1—C8110.41 (12)C5—C6—H6A110.0
C7A—C1—C8115.43 (13)C7—C6—H6A110.0
O1—C3—O2121.03 (16)C5—C6—H6B110.0
O1—C3—C3A130.20 (17)C7—C6—H6B110.0
O2—C3—C3A108.77 (14)H6A—C6—H6B108.4
C7A—C3A—C3108.09 (15)C6'—C5'—H5'A109.3
C7A—C3A—C4124.73 (15)C4—C5'—H5'A109.3
C3—C3A—C4127.18 (15)C6'—C5'—H5'B109.3
C5—C4—C3A111.4 (6)C4—C5'—H5'B109.3
C5—C4—C5'23.5 (4)H5'A—C5'—H5'B107.9
C3A—C4—C5'109.0 (3)C7—C6'—H6'A109.6
C4—C5—C6110.8 (10)C5'—C6'—H6'A109.6
C5—C6—C7108.6 (10)C7—C6'—H6'B109.6
C6'—C5'—C4111.8 (5)C5'—C6'—H6'B109.6
C7—C6'—C5'110.3 (5)H6'A—C6'—H6'B108.1
C7A—C7—C6'110.2 (2)C7A—C7—H7A110.3
C7A—C7—C6107.2 (3)C6'—C7—H7A76.8
C6'—C7—C635.3 (3)C6—C7—H7A110.3
C3A—C7A—C7124.51 (16)C7A—C7—H7B110.3
C3A—C7A—C1110.29 (14)C6'—C7—H7B133.9
C7—C7A—C1125.19 (15)C6—C7—H7B110.3
C13—C8—C1113.43 (13)H7A—C7—H7B108.5
C13—C8—C9112.93 (13)C7A—C7—H7A'110.1
C1—C8—C9112.55 (13)C6'—C7—H7A'110.3
C14—C9—C10111.48 (14)C6—C7—H7A'137.4
C14—C9—C8113.31 (14)H7A—C7—H7A'36.5
C10—C9—C8110.30 (14)H7B—C7—H7A'75.0
C11—C10—C9113.83 (15)C7A—C7—H7B'109.3
C12—C11—C10111.12 (15)C6'—C7—H7B'109.1
C11—C12—C13111.34 (15)C6—C7—H7B'77.6
C12—C13—C8111.30 (14)H7A—C7—H7B'134.7
O3—C14—O4122.43 (16)H7B—C7—H7B'35.2
O3—C14—C9122.41 (15)H7A'—C7—H7B'108.0
O4—C14—C9115.16 (15)C13—C8—H8105.7
C14—O3—H3109.5C1—C8—H8105.7
C14—O4—H4109.5C9—C8—H8105.7
O2—C1—H1109.1C14—C9—H9107.1
C7A—C1—H1109.1C10—C9—H9107.1
C8—C1—H1109.1C8—C9—H9107.1
C5—C4—H4A109.3C11—C10—H10A108.8
C3A—C4—H4A109.3C9—C10—H10A108.8
C5'—C4—H4A129.1C11—C10—H10B108.8
C5—C4—H4B109.3C9—C10—H10B108.8
C3A—C4—H4B109.3H10A—C10—H10B107.7
C5'—C4—H4B89.2C12—C11—H11A109.4
H4A—C4—H4B108.0C10—C11—H11A109.4
C5—C4—H4A'126.9C12—C11—H11B109.4
C3A—C4—H4A'110.0C10—C11—H11B109.4
C5'—C4—H4A'110.3H11A—C11—H11B108.0
H4A—C4—H4A'86.2C11—C12—H12A109.4
H4B—C4—H4A'23.5C13—C12—H12A109.4
C5—C4—H4B'87.7C11—C12—H12B109.4
C3A—C4—H4B'109.8C13—C12—H12B109.4
C5'—C4—H4B'109.9H12A—C12—H12B108.0
H4A—C4—H4B'24.1C12—C13—H13A109.4
H4B—C4—H4B'127.1C8—C13—H13A109.4
H4A'—C4—H4B'107.9C12—C13—H13B109.4
C4—C5—H5A109.5C8—C13—H13B109.4
C6—C5—H5A109.5H13A—C13—H13B108.0
C4—C5—H5B109.5
C3—O2—C1—C7A1.03 (15)C6—C7—C7A—C3A21.1 (6)
C3—O2—C1—C8123.03 (14)C6'—C7—C7A—C1162.7 (4)
C1—O2—C3—O1179.32 (15)C6—C7—C7A—C1160.1 (5)
C1—O2—C3—C3A0.96 (16)O2—C1—C7A—C3A0.74 (17)
O1—C3—C3A—C7A179.84 (17)C8—C1—C7A—C3A119.97 (15)
O2—C3—C3A—C7A0.48 (18)O2—C1—C7A—C7178.19 (15)
O1—C3—C3A—C40.2 (3)C8—C1—C7A—C761.1 (2)
O2—C3—C3A—C4179.52 (15)O2—C1—C8—C1359.94 (17)
C7A—C3A—C4—C512.1 (6)C7A—C1—C8—C1356.91 (18)
C3—C3A—C4—C5167.9 (6)O2—C1—C8—C969.83 (17)
C7A—C3A—C4—C5'12.8 (4)C7A—C1—C8—C9173.32 (13)
C3—C3A—C4—C5'167.2 (3)C13—C8—C9—C1474.98 (18)
C3A—C4—C5—C644.4 (14)C1—C8—C9—C1455.04 (18)
C5'—C4—C5—C644.1 (17)C13—C8—C9—C1050.79 (19)
C4—C5—C6—C765.8 (15)C1—C8—C9—C10179.19 (14)
C5—C4—C5'—C6'56 (2)C14—C9—C10—C1176.23 (19)
C3A—C4—C5'—C6'44.4 (7)C8—C9—C10—C1150.6 (2)
C4—C5'—C6'—C764.0 (9)C9—C10—C11—C1253.7 (2)
C5'—C6'—C7—C7A47.0 (7)C10—C11—C12—C1355.9 (2)
C5'—C6'—C7—C644.6 (6)C11—C12—C13—C856.7 (2)
C5—C6—C7—C7A51.4 (12)C1—C8—C13—C12175.74 (13)
C5—C6—C7—C6'49.3 (9)C9—C8—C13—C1254.69 (19)
C3—C3A—C7A—C7178.75 (16)C10—C9—C14—O353.4 (2)
C4—C3A—C7A—C71.2 (3)C8—C9—C14—O371.7 (2)
C3—C3A—C7A—C10.20 (18)C10—C9—C14—O4126.31 (16)
C4—C3A—C7A—C1179.80 (15)C8—C9—C14—O4108.56 (17)
C6'—C7—C7A—C3A16.1 (4)
(II) (±)-cis-2-(3-Oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl)- cyclohexanecarboxylic acid top
Crystal data top
C15H20O4Dx = 1.240 Mg m3
Mr = 264.32Melting point = 472–476 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.372 (7) ÅCell parameters from 41 reflections
b = 10.467 (9) Åθ = 1.7–16.7°
c = 11.901 (16) ŵ = 0.09 mm1
β = 91.11 (7)°T = 293 K
V = 1416 (2) Å3Rectangular prism, colorless
Z = 40.50 × 0.30 × 0.25 mm
F(000) = 568
Data collection top
Siemens P4
diffractometer
Rint = 0.025
Radiation source: normal-focus sealed tubeθmax = 25.0°, θmin = 2.6°
Graphite monochromatorh = 1313
2θ/θ scansk = 012
3242 measured reflectionsl = 014
2498 independent reflections3 standard reflections every 97 reflections
1151 reflections with I > 2σ(I) intensity decay: variation < 3.0%
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.237H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0941P)2 + 0.6553P]
where P = (Fo2 + 2Fc2)/3
2498 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.32 e Å3
Special details top

Experimental. Crystal mounted on glass fiber using epoxy resin

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
O10.5226 (3)0.7519 (4)0.5555 (3)0.1007 (11)
O20.6491 (2)0.6445 (3)0.4484 (2)0.0717 (8)
O30.8875 (2)0.4831 (3)0.4112 (3)0.0849 (9)
O40.9972 (3)0.6557 (3)0.4385 (3)0.0884 (10)
C10.6439 (3)0.5640 (4)0.3489 (3)0.0614 (10)
C30.5380 (3)0.6856 (4)0.4745 (3)0.0701 (11)
C3A0.4564 (3)0.6343 (4)0.3910 (3)0.0637 (10)
C40.3269 (3)0.6592 (5)0.3855 (4)0.0858 (13)
C50.2799 (5)0.6207 (9)0.2736 (6)0.151 (3)
C60.3251 (5)0.5033 (6)0.2291 (6)0.129 (2)
C7A0.5148 (3)0.5630 (4)0.3177 (3)0.0632 (10)
C70.4592 (4)0.4927 (4)0.2213 (4)0.0815 (13)
C80.7280 (3)0.6140 (4)0.2594 (3)0.0640 (10)
C90.8393 (3)0.6770 (4)0.3083 (3)0.0619 (10)
C100.9204 (4)0.7220 (4)0.2126 (4)0.0837 (13)
C110.9509 (4)0.6126 (5)0.1344 (4)0.1010 (16)
C120.8406 (5)0.5556 (6)0.0836 (4)0.1101 (18)
C130.7563 (4)0.5088 (4)0.1740 (3)0.0832 (13)
C140.9083 (3)0.5958 (4)0.3896 (3)0.0645 (10)
H10.66780.47720.37010.074*
H41.044 (3)0.593 (4)0.498 (3)0.080*
H4A0.28810.61090.44370.103*
H4B0.31180.74930.39790.103*
H5A0.19510.61310.27810.181*
H5B0.29620.68860.22070.181*
H6A0.29130.49110.15440.155*
H6B0.29760.43370.27560.155*
H7A0.48260.40360.22370.098*
H7B0.48490.52890.15090.098*
H8A0.68520.68070.21770.077*
H9A0.81460.75350.34900.074*
H10A0.88130.78900.16980.100*
H10B0.99230.75730.24510.100*
H11A1.00070.64390.07510.121*
H11B0.99410.54750.17600.121*
H12A0.86140.48440.03570.132*
H12B0.80110.61920.03720.132*
H13A0.79150.43670.21330.100*
H13B0.68380.47970.13820.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.094 (2)0.119 (3)0.089 (2)0.0041 (19)0.0186 (17)0.031 (2)
O20.0554 (14)0.097 (2)0.0625 (15)0.0054 (14)0.0015 (12)0.0066 (14)
O30.0748 (19)0.0740 (19)0.105 (2)0.0019 (16)0.0281 (16)0.0185 (17)
O40.0767 (19)0.0802 (19)0.107 (2)0.0083 (16)0.0293 (17)0.0167 (17)
C10.060 (2)0.068 (2)0.057 (2)0.0058 (19)0.0041 (16)0.0042 (18)
C30.064 (2)0.074 (3)0.072 (2)0.003 (2)0.007 (2)0.002 (2)
C3A0.054 (2)0.064 (2)0.073 (2)0.0038 (19)0.0023 (18)0.008 (2)
C40.054 (2)0.101 (3)0.102 (3)0.000 (2)0.002 (2)0.023 (3)
C50.067 (3)0.210 (8)0.175 (6)0.019 (4)0.041 (4)0.019 (6)
C60.091 (4)0.129 (5)0.165 (6)0.019 (4)0.055 (4)0.023 (4)
C7A0.060 (2)0.059 (2)0.070 (2)0.0066 (19)0.0123 (18)0.0085 (19)
C70.086 (3)0.071 (3)0.086 (3)0.012 (2)0.025 (2)0.003 (2)
C80.059 (2)0.076 (2)0.057 (2)0.0153 (19)0.0013 (16)0.0016 (19)
C90.057 (2)0.066 (2)0.062 (2)0.0115 (18)0.0054 (17)0.0067 (18)
C100.074 (3)0.090 (3)0.087 (3)0.018 (2)0.015 (2)0.023 (2)
C110.089 (3)0.130 (4)0.085 (3)0.033 (3)0.027 (3)0.022 (3)
C120.122 (4)0.144 (5)0.064 (3)0.041 (4)0.011 (3)0.010 (3)
C130.086 (3)0.092 (3)0.072 (3)0.020 (3)0.004 (2)0.017 (2)
C140.054 (2)0.074 (3)0.065 (2)0.011 (2)0.0003 (18)0.003 (2)
Geometric parameters (Å, º) top
O1—C31.203 (5)O4—H41.09 (4)
O2—C31.375 (5)C1—H10.9800
O2—C11.454 (4)C4—H4A0.9700
O3—C141.231 (5)C4—H4B0.9700
O4—C141.315 (5)C5—H5A0.9700
C1—C7A1.508 (5)C5—H5B0.9700
C1—C81.537 (5)C6—H6A0.9700
C3—C3A1.449 (6)C6—H6B0.9700
C3A—C7A1.334 (5)C7—H7A0.9700
C3A—C41.496 (5)C7—H7B0.9700
C4—C51.482 (8)C8—H8A0.9800
C5—C61.436 (8)C9—H9A0.9800
C6—C71.534 (7)C10—H10A0.9700
C7A—C71.493 (5)C10—H10B0.9700
C8—C91.532 (5)C11—H11A0.9700
C8—C131.536 (5)C11—H11B0.9700
C9—C141.498 (5)C12—H12A0.9700
C9—C101.552 (5)C12—H12B0.9700
C10—C111.520 (6)C13—H13A0.9700
C11—C121.506 (7)C13—H13B0.9700
C12—C131.535 (6)
C3—O2—C1110.0 (3)C4—C5—H5A108.3
O2—C1—C7A103.2 (3)C6—C5—H5B108.3
O2—C1—C8110.6 (3)C4—C5—H5B108.3
C7A—C1—C8116.6 (3)H5A—C5—H5B107.4
O1—C3—O2120.7 (4)C5—C6—H6A108.1
O1—C3—C3A131.4 (4)C7—C6—H6A108.1
O2—C3—C3A107.9 (3)C5—C6—H6B108.1
C7A—C3A—C3109.6 (3)C7—C6—H6B108.1
C7A—C3A—C4124.8 (4)H6A—C6—H6B107.3
C3—C3A—C4125.6 (4)C7A—C7—H7A109.9
C5—C4—C3A109.2 (4)C6—C7—H7A109.9
C6—C5—C4116.0 (5)C7A—C7—H7B109.9
C5—C6—C7116.6 (5)C6—C7—H7B109.9
C3A—C7A—C7124.7 (4)H7A—C7—H7B108.3
C3A—C7A—C1109.3 (3)C9—C8—H8A106.5
C7—C7A—C1126.0 (4)C13—C8—H8A106.5
C7A—C7—C6108.9 (4)C1—C8—H8A106.5
C9—C8—C13112.2 (3)C14—C9—H9A107.2
C9—C8—C1113.8 (3)C8—C9—H9A107.2
C13—C8—C1110.8 (3)C10—C9—H9A107.2
C14—C9—C8114.8 (3)C11—C10—H10A109.3
C14—C9—C10109.6 (3)C9—C10—H10A109.3
C8—C9—C10110.5 (3)C11—C10—H10B109.3
C11—C10—C9111.5 (4)C9—C10—H10B109.3
C12—C11—C10110.3 (4)H10A—C10—H10B108.0
C11—C12—C13111.8 (4)C12—C11—H11A109.6
C12—C13—C8112.2 (4)C10—C11—H11A109.6
O3—C14—O4120.9 (4)C12—C11—H11B109.6
O3—C14—C9125.3 (4)C10—C11—H11B109.6
O4—C14—C9113.8 (4)H11A—C11—H11B108.1
C14—O4—H4111 (2)C11—C12—H12A109.2
O2—C1—H1108.7C13—C12—H12A109.2
C7A—C1—H1108.7C11—C12—H12B109.2
C8—C1—H1108.7C13—C12—H12B109.2
C5—C4—H4A109.8H12A—C12—H12B107.9
C3A—C4—H4A109.8C12—C13—H13A109.2
C5—C4—H4B109.8C8—C13—H13A109.2
C3A—C4—H4B109.8C12—C13—H13B109.2
H4A—C4—H4B108.3C8—C13—H13B109.2
C6—C5—H5A108.3H13A—C13—H13B107.9
C3—O2—C1—C7A0.6 (4)C1—C7A—C7—C6172.6 (4)
C3—O2—C1—C8125.9 (3)C5—C6—C7—C7A34.1 (7)
C1—O2—C3—O1178.8 (4)O2—C1—C8—C932.7 (4)
C1—O2—C3—C3A0.9 (4)C7A—C1—C8—C9150.1 (3)
O1—C3—C3A—C7A178.7 (4)O2—C1—C8—C13160.2 (3)
O2—C3—C3A—C7A0.9 (4)C7A—C1—C8—C1382.4 (4)
O1—C3—C3A—C42.6 (7)C13—C8—C9—C1472.6 (4)
O2—C3—C3A—C4177.8 (4)C1—C8—C9—C1454.2 (4)
C7A—C3A—C4—C513.9 (7)C13—C8—C9—C1051.9 (4)
C3—C3A—C4—C5164.7 (5)C1—C8—C9—C10178.7 (3)
C3A—C4—C5—C641.4 (8)C14—C9—C10—C1171.6 (5)
C4—C5—C6—C754.8 (9)C8—C9—C10—C1155.9 (4)
C3—C3A—C7A—C7178.6 (4)C9—C10—C11—C1258.5 (5)
C4—C3A—C7A—C72.6 (6)C10—C11—C12—C1357.2 (6)
C3—C3A—C7A—C10.6 (4)C11—C12—C13—C853.9 (5)
C4—C3A—C7A—C1178.2 (4)C9—C8—C13—C1251.4 (5)
O2—C1—C7A—C3A0.0 (4)C1—C8—C13—C12179.8 (3)
C8—C1—C7A—C3A121.3 (4)C8—C9—C14—O36.3 (5)
O2—C1—C7A—C7179.2 (3)C10—C9—C14—O3118.8 (4)
C8—C1—C7A—C759.5 (5)C8—C9—C14—O4173.9 (3)
C3A—C7A—C7—C66.5 (6)C10—C9—C14—O461.1 (4)
 

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