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The molecular structures of two chiral cyclo­hexanones based on R-(-)-carvone, C17H26O3, (I), and C17H23NO, (II), are reported here. The six-membered ring in (I) is in a chair conformation with the two fused five-membered rings of the furo­furan­yl substituent in a cis configuration. Compound (II) contains a decalin group; one ring has the chair form whilst the other is in a half-boat conformation. Both products have been characterized spectroscopically, however, neither NMR nor IR results could prove the stereochemistry at each chiral centre unambiguously. The crystal analyses were used to ex­amine conformational properties of the compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008805/gg1013sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008805/gg1013Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008805/gg1013IIsup3.hkl
Contains datablock II

CCDC references: 150871; 150872

Computing details top

For both compounds, data collection: Locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: PLATON.

(I) top
Crystal data top
C17H26O3Dx = 1.190 Mg m3
Mr = 278.38Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 6.3914 (5) Åθ = 9.9–13.8°
b = 9.0264 (6) ŵ = 0.08 mm1
c = 26.9292 (19) ÅT = 150 K
V = 1553.58 (19) Å3Block, colourless
Z = 40.50 × 0.30 × 0.30 mm
F(000) = 608
Data collection top
Enraf-Nonius CAD4
diffractometer
Rint = 0.050
Radiation source: rotating anodeθmax = 27.5°, θmin = 1.5°
Graphite monochromatorh = 80
ω scansk = 1111
4168 measured reflectionsl = 340
2084 independent reflections3 standard reflections every 60 min
1522 reflections with I > 2σ(I) intensity decay: <1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.1569P]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.001
2084 reflectionsΔρmax = 0.26 e Å3
184 parametersΔρmin = 0.24 e Å3
0 restraintsAbsolute structure: see experimental
Primary atom site location: structure-invariant direct methods
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
O11.4226 (3)0.4390 (2)0.13696 (8)0.0351 (5)
O20.8862 (3)0.3659 (3)0.28360 (8)0.0376 (6)
O31.0731 (3)0.3217 (2)0.21038 (7)0.0262 (4)
C11.2368 (4)0.4496 (3)0.12845 (9)0.0242 (6)
C21.1325 (5)0.5985 (3)0.12409 (10)0.0260 (6)
H2A1.24010.67720.12590.031*
H2B1.03550.61220.15240.031*
C31.0096 (4)0.6145 (3)0.07503 (10)0.0246 (6)
H31.11290.61030.04720.029*
C40.8606 (4)0.4828 (3)0.06909 (10)0.0246 (6)
H4A0.78870.49060.03660.029*
H4B0.75260.48750.09540.029*
C50.9730 (4)0.3323 (3)0.07209 (9)0.0226 (6)
H50.86330.25330.07120.027*
C61.0980 (4)0.3131 (3)0.12141 (10)0.0224 (6)
C70.9466 (4)0.3109 (3)0.16644 (9)0.0211 (5)
H70.85220.39900.16460.025*
C80.8148 (5)0.1722 (3)0.17446 (10)0.0266 (6)
H8A0.88900.08280.16250.032*
H8B0.67880.18020.15710.032*
C90.7842 (4)0.1670 (3)0.23093 (10)0.0248 (6)
H90.79070.06260.24330.030*
C100.5907 (5)0.2468 (3)0.25177 (12)0.0308 (7)
H10A0.48180.25870.22590.037*
H10B0.53070.19190.28020.037*
C110.6756 (5)0.3952 (4)0.26799 (12)0.0364 (8)
H11A0.67360.46670.24010.044*
H11B0.59190.43600.29570.044*
C120.9681 (4)0.2578 (3)0.25116 (11)0.0264 (6)
H121.06600.19150.26970.032*
C131.2303 (5)0.1721 (3)0.12056 (11)0.0293 (7)
H13A1.14440.08880.10920.044*
H13B1.28260.15140.15410.044*
H13C1.34880.18560.09790.044*
C141.1154 (5)0.3096 (3)0.02692 (10)0.0305 (7)
H14A1.14900.20410.02360.046*
H14B1.24480.36630.03140.046*
H14C1.04330.34380.00310.046*
C150.8984 (5)0.7613 (3)0.07182 (11)0.0302 (7)
C160.9433 (6)0.8556 (4)0.03615 (13)0.0507 (10)
H16A0.87210.94780.03430.061*
H16B1.04700.83150.01220.061*
C170.7351 (6)0.7955 (4)0.11048 (14)0.0465 (9)
H17A0.80340.81270.14260.070*
H17B0.63840.71170.11330.070*
H17C0.65730.88440.10070.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0257 (11)0.0384 (12)0.0412 (12)0.0039 (11)0.0023 (10)0.0050 (10)
O20.0344 (12)0.0455 (13)0.0328 (11)0.0144 (11)0.0036 (10)0.0131 (10)
O30.0228 (10)0.0350 (10)0.0209 (9)0.0092 (10)0.0024 (8)0.0016 (8)
C10.0236 (14)0.0334 (16)0.0155 (12)0.0011 (13)0.0011 (12)0.0049 (11)
C20.0276 (16)0.0250 (14)0.0254 (14)0.0071 (13)0.0031 (13)0.0012 (11)
C30.0266 (14)0.0253 (14)0.0217 (13)0.0023 (13)0.0020 (13)0.0006 (12)
C40.0247 (14)0.0293 (14)0.0198 (12)0.0011 (13)0.0018 (12)0.0004 (11)
C50.0240 (13)0.0220 (13)0.0219 (13)0.0030 (12)0.0019 (12)0.0019 (11)
C60.0201 (13)0.0238 (13)0.0232 (13)0.0007 (13)0.0020 (12)0.0005 (11)
C70.0209 (13)0.0228 (12)0.0196 (12)0.0013 (12)0.0024 (11)0.0017 (11)
C80.0255 (14)0.0279 (14)0.0265 (14)0.0027 (13)0.0000 (12)0.0022 (12)
C90.0255 (15)0.0183 (13)0.0305 (14)0.0002 (13)0.0039 (13)0.0039 (11)
C100.0258 (15)0.0329 (16)0.0336 (16)0.0014 (15)0.0019 (14)0.0005 (14)
C110.0373 (18)0.0326 (17)0.0395 (17)0.0046 (15)0.0114 (15)0.0019 (14)
C120.0232 (15)0.0318 (15)0.0243 (13)0.0023 (13)0.0032 (13)0.0065 (13)
C130.0288 (15)0.0268 (14)0.0323 (15)0.0057 (14)0.0023 (14)0.0001 (13)
C140.0345 (16)0.0326 (15)0.0246 (14)0.0014 (16)0.0007 (13)0.0016 (12)
C150.0344 (16)0.0232 (14)0.0329 (15)0.0003 (15)0.0112 (15)0.0015 (12)
C160.066 (3)0.0337 (18)0.052 (2)0.003 (2)0.007 (2)0.0102 (15)
C170.045 (2)0.0302 (17)0.064 (2)0.0143 (17)0.0049 (19)0.0055 (16)
Geometric parameters (Å, º) top
O1—C11.213 (3)C8—H8A0.9900
O2—C121.410 (4)C8—H8B0.9900
O2—C111.435 (4)C9—C121.533 (4)
O3—C121.410 (3)C9—C101.537 (4)
O3—C71.436 (3)C9—H91.0000
C1—C21.505 (4)C10—C111.510 (4)
C1—C61.530 (4)C10—H10A0.9900
C2—C31.544 (4)C10—H10B0.9900
C2—H2A0.9900C11—H11A0.9900
C2—H2B0.9900C11—H11B0.9900
C3—C151.506 (4)C12—H121.0000
C3—C41.531 (4)C13—H13A0.9800
C3—H31.0000C13—H13B0.9800
C4—C51.539 (4)C13—H13C0.9800
C4—H4A0.9900C14—H14A0.9800
C4—H4B0.9900C14—H14B0.9800
C5—C141.533 (4)C14—H14C0.9800
C5—C61.560 (4)C15—C161.315 (4)
C5—H51.0000C15—C171.506 (5)
C6—C131.528 (4)C16—H16A0.9500
C6—C71.551 (4)C16—H16B0.9500
C7—C81.524 (4)C17—H17A0.9800
C7—H71.0000C17—H17B0.9800
C8—C91.534 (4)C17—H17C0.9800
C12—O2—C11107.1 (2)C8—C9—C10116.8 (2)
C12—O3—C7110.2 (2)C12—C9—C10103.7 (2)
O1—C1—C2121.3 (3)C8—C9—H9110.7
O1—C1—C6121.8 (3)C12—C9—H9110.7
C2—C1—C6116.9 (2)C10—C9—H9110.7
C1—C2—C3112.1 (2)C11—C10—C9103.4 (2)
C1—C2—H2A109.2C11—C10—H10A111.1
C3—C2—H2A109.2C9—C10—H10A111.1
C1—C2—H2B109.2C11—C10—H10B111.1
C3—C2—H2B109.2C9—C10—H10B111.1
H2A—C2—H2B107.9H10A—C10—H10B109.0
C15—C3—C4112.6 (2)O2—C11—C10104.9 (3)
C15—C3—C2111.8 (2)O2—C11—H11A110.8
C4—C3—C2109.5 (2)C10—C11—H11A110.8
C15—C3—H3107.6O2—C11—H11B110.8
C4—C3—H3107.6C10—C11—H11B110.8
C2—C3—H3107.6H11A—C11—H11B108.8
C3—C4—C5112.9 (2)O2—C12—O3112.1 (2)
C3—C4—H4A109.0O2—C12—C9107.8 (2)
C5—C4—H4A109.0O3—C12—C9107.9 (2)
C3—C4—H4B109.0O2—C12—H12109.7
C5—C4—H4B109.0O3—C12—H12109.7
H4A—C4—H4B107.8C9—C12—H12109.7
C14—C5—C4110.7 (2)C6—C13—H13A109.5
C14—C5—C6110.9 (2)C6—C13—H13B109.5
C4—C5—C6112.5 (2)H13A—C13—H13B109.5
C14—C5—H5107.5C6—C13—H13C109.5
C4—C5—H5107.5H13A—C13—H13C109.5
C6—C5—H5107.5H13B—C13—H13C109.5
C13—C6—C1110.6 (2)C5—C14—H14A109.5
C13—C6—C7110.2 (2)C5—C14—H14B109.5
C1—C6—C7106.0 (2)H14A—C14—H14B109.5
C13—C6—C5111.3 (2)C5—C14—H14C109.5
C1—C6—C5108.2 (2)H14A—C14—H14C109.5
C7—C6—C5110.3 (2)H14B—C14—H14C109.5
O3—C7—C8104.5 (2)C16—C15—C17121.6 (3)
O3—C7—C6107.0 (2)C16—C15—C3120.5 (3)
C8—C7—C6117.8 (2)C17—C15—C3117.9 (3)
O3—C7—H7109.1C15—C16—H16A120.0
C8—C7—H7109.1C15—C16—H16B120.0
C6—C7—H7109.1H16A—C16—H16B120.0
C7—C8—C9103.7 (2)C15—C17—H17A109.5
C7—C8—H8A111.0C15—C17—H17B109.5
C9—C8—H8A111.0H17A—C17—H17B109.5
C7—C8—H8B111.0C15—C17—H17C109.5
C9—C8—H8B111.0H17A—C17—H17C109.5
H8A—C8—H8B109.0H17B—C17—H17C109.5
C8—C9—C12103.8 (2)
O1—C1—C2—C3126.6 (3)C5—C6—C7—O3169.1 (2)
C6—C1—C2—C353.1 (3)C13—C6—C7—C849.7 (3)
C1—C2—C3—C15177.7 (2)C1—C6—C7—C8169.4 (2)
C1—C2—C3—C452.3 (3)C5—C6—C7—C873.7 (3)
C15—C3—C4—C5179.7 (2)O3—C7—C8—C931.5 (3)
C2—C3—C4—C555.3 (3)C6—C7—C8—C9150.0 (2)
C3—C4—C5—C1468.2 (3)C7—C8—C9—C1223.0 (3)
C3—C4—C5—C656.5 (3)C7—C8—C9—C1090.3 (3)
O1—C1—C6—C136.7 (4)C8—C9—C10—C1197.2 (3)
C2—C1—C6—C13173.0 (2)C12—C9—C10—C1116.2 (3)
O1—C1—C6—C7112.8 (3)C12—O2—C11—C1037.2 (3)
C2—C1—C6—C767.5 (3)C9—C10—C11—O232.3 (3)
O1—C1—C6—C5128.8 (3)C11—O2—C12—O392.1 (3)
C2—C1—C6—C550.9 (3)C11—O2—C12—C926.5 (3)
C14—C5—C6—C1348.1 (3)C7—O3—C12—O2104.6 (3)
C4—C5—C6—C13172.7 (2)C7—O3—C12—C913.9 (3)
C14—C5—C6—C173.7 (3)C8—C9—C12—O2127.9 (2)
C4—C5—C6—C150.9 (3)C10—C9—C12—O25.4 (3)
C14—C5—C6—C7170.8 (2)C8—C9—C12—O36.6 (3)
C4—C5—C6—C764.6 (3)C10—C9—C12—O3115.8 (2)
C12—O3—C7—C828.8 (3)C4—C3—C15—C16117.5 (3)
C12—O3—C7—C6154.5 (2)C2—C3—C15—C16118.9 (3)
C13—C6—C7—O367.5 (3)C4—C3—C15—C1762.3 (3)
C1—C6—C7—O352.2 (3)C2—C3—C15—C1761.3 (3)
(II) top
Crystal data top
C17H23NODx = 1.148 Mg m3
Mr = 257.36Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 8.3419 (9) Åθ = 9.9–15.1°
b = 12.3902 (10) ŵ = 0.07 mm1
c = 14.4052 (14) ÅT = 150 K
V = 1488.9 (2) Å3Block, yellow
Z = 40.30 × 0.30 × 0.30 mm
F(000) = 560
Data collection top
Enraf-Nonius CAD4T
diffractometer
Rint = 0.100
Radiation source: rotating anodeθmax = 25.0°, θmin = 2.2°
Graphite monochromatorh = 09
ω scansk = 1414
5872 measured reflectionsl = 1717
1534 independent reflections3 standard reflections every 60 min
1059 reflections with I > 2σ(I) intensity decay: <1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0418P)2 + 0.0185P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
1534 reflectionsΔρmax = 0.16 e Å3
176 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: see experimental
Primary atom site location: structure-invariant direct methods
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
O10.0718 (4)0.2874 (2)0.02667 (17)0.0422 (8)
N10.0928 (4)0.6141 (2)0.1741 (3)0.0426 (10)
C10.2051 (5)0.3654 (3)0.0995 (3)0.0291 (10)
H10.30650.34940.07270.035*
C20.0615 (5)0.3249 (3)0.0515 (2)0.0278 (9)
C30.0963 (5)0.3372 (3)0.0999 (3)0.0278 (9)
H3A0.16580.27480.08480.033*
H3B0.15020.40350.07750.033*
C40.0739 (5)0.3439 (3)0.2040 (2)0.0245 (9)
H4A0.03220.27420.22720.029*
H4B0.17910.35700.23380.029*
C50.0430 (4)0.4350 (3)0.2313 (2)0.0225 (9)
C60.0728 (4)0.4289 (3)0.3377 (2)0.0274 (9)
H60.11590.35490.34940.033*
C70.2049 (4)0.5060 (3)0.3678 (3)0.0328 (10)
H7A0.21870.50160.43590.039*
H7B0.17360.58090.35200.039*
C80.3636 (5)0.4789 (3)0.3202 (3)0.0332 (10)
H80.44170.53600.33920.040*
C90.3499 (4)0.4849 (3)0.2131 (3)0.0262 (9)
C100.2034 (4)0.4232 (3)0.1781 (3)0.0235 (9)
C110.3324 (5)0.6045 (3)0.1839 (3)0.0399 (11)
H11A0.43170.64340.19810.060*
H11B0.24320.63740.21790.060*
H11C0.31130.60860.11700.060*
C120.5044 (4)0.4439 (3)0.1675 (3)0.0396 (11)
H12A0.51150.36550.17490.059*
H12B0.59710.47810.19720.059*
H12C0.50330.46210.10130.059*
C130.4303 (5)0.3714 (3)0.3559 (3)0.0483 (12)
H13A0.42450.36990.42380.073*
H13B0.54220.36380.33630.073*
H13C0.36690.31180.33040.073*
C140.0777 (5)0.4374 (4)0.3966 (3)0.0425 (11)
C150.1657 (6)0.5369 (4)0.4007 (3)0.0586 (14)
H15A0.26090.52730.43970.088*
H15B0.19870.55790.33800.088*
H15C0.09760.59350.42730.088*
C160.1212 (6)0.3492 (4)0.4495 (3)0.0579 (14)
H16A0.21120.35350.48970.070*
H16B0.06120.28420.44560.070*
C170.0307 (4)0.5382 (3)0.2024 (3)0.0282 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0486 (18)0.0500 (18)0.0281 (16)0.0001 (15)0.0006 (17)0.0145 (14)
N10.034 (2)0.0274 (18)0.067 (3)0.0033 (17)0.008 (2)0.0054 (19)
C10.027 (2)0.030 (2)0.030 (2)0.0013 (19)0.002 (2)0.0022 (18)
C20.039 (2)0.021 (2)0.023 (2)0.0038 (19)0.002 (2)0.0001 (16)
C30.029 (2)0.027 (2)0.027 (2)0.0020 (19)0.004 (2)0.0041 (17)
C40.023 (2)0.0235 (18)0.027 (2)0.0011 (16)0.002 (2)0.0018 (15)
C50.025 (2)0.0195 (18)0.0232 (19)0.0019 (16)0.0015 (18)0.0014 (16)
C60.027 (2)0.033 (2)0.022 (2)0.0012 (18)0.001 (2)0.0059 (18)
C70.033 (2)0.036 (2)0.029 (2)0.005 (2)0.002 (2)0.0086 (18)
C80.029 (2)0.034 (2)0.036 (2)0.0057 (19)0.004 (2)0.0072 (19)
C90.019 (2)0.026 (2)0.033 (2)0.0001 (16)0.000 (2)0.0027 (17)
C100.024 (2)0.0182 (19)0.028 (2)0.0020 (16)0.0033 (19)0.0037 (17)
C110.036 (2)0.035 (2)0.049 (3)0.008 (2)0.003 (2)0.005 (2)
C120.024 (2)0.046 (2)0.048 (3)0.001 (2)0.002 (2)0.008 (2)
C130.035 (2)0.056 (3)0.054 (3)0.003 (2)0.013 (3)0.013 (2)
C140.036 (3)0.066 (3)0.025 (2)0.013 (2)0.001 (2)0.017 (2)
C150.048 (3)0.080 (4)0.048 (3)0.011 (3)0.009 (3)0.025 (3)
C160.058 (3)0.073 (3)0.043 (3)0.015 (3)0.016 (3)0.003 (3)
C170.024 (2)0.026 (2)0.034 (2)0.0033 (18)0.001 (2)0.0068 (18)
Geometric parameters (Å, º) top
O1—C21.222 (4)C8—C91.548 (6)
N1—C171.148 (4)C8—H81.0000
C1—C101.341 (5)C9—C101.527 (5)
C1—C21.471 (5)C9—C121.533 (5)
C1—H10.9500C9—C111.548 (5)
C2—C31.497 (5)C11—H11A0.9800
C3—C41.514 (5)C11—H11B0.9800
C3—H3A0.9900C11—H11C0.9800
C3—H3B0.9900C12—H12A0.9800
C4—C51.542 (5)C12—H12B0.9800
C4—H4A0.9900C12—H12C0.9800
C4—H4B0.9900C13—H13A0.9800
C5—C171.479 (5)C13—H13B0.9800
C5—C101.549 (5)C13—H13C0.9800
C5—C61.555 (5)C14—C161.381 (6)
C6—C141.519 (5)C14—C151.436 (6)
C6—C71.521 (5)C15—H15A0.9800
C6—H61.0000C15—H15B0.9800
C7—C81.528 (5)C15—H15C0.9800
C7—H7A0.9900C16—H16A0.9500
C7—H7B0.9900C16—H16B0.9500
C8—C131.532 (5)
C10—C1—C2124.8 (4)C9—C8—H8106.6
C10—C1—H1117.6C10—C9—C12111.4 (3)
C2—C1—H1117.6C10—C9—C11108.3 (3)
O1—C2—C1120.4 (4)C12—C9—C11106.2 (3)
O1—C2—C3122.0 (4)C10—C9—C8111.3 (3)
C1—C2—C3117.6 (3)C12—C9—C8110.4 (3)
C2—C3—C4111.0 (3)C11—C9—C8108.9 (3)
C2—C3—H3A109.4C1—C10—C9122.5 (3)
C4—C3—H3A109.4C1—C10—C5118.5 (3)
C2—C3—H3B109.4C9—C10—C5118.8 (3)
C4—C3—H3B109.4C9—C11—H11A109.5
H3A—C3—H3B108.0C9—C11—H11B109.5
C3—C4—C5111.8 (3)H11A—C11—H11B109.5
C3—C4—H4A109.3C9—C11—H11C109.5
C5—C4—H4A109.3H11A—C11—H11C109.5
C3—C4—H4B109.3H11B—C11—H11C109.5
C5—C4—H4B109.3C9—C12—H12A109.5
H4A—C4—H4B107.9C9—C12—H12B109.5
C17—C5—C4107.4 (3)H12A—C12—H12B109.5
C17—C5—C10107.6 (3)C9—C12—H12C109.5
C4—C5—C10110.6 (3)H12A—C12—H12C109.5
C17—C5—C6112.7 (3)H12B—C12—H12C109.5
C4—C5—C6108.5 (3)C8—C13—H13A109.5
C10—C5—C6110.2 (3)C8—C13—H13B109.5
C14—C6—C7113.4 (3)H13A—C13—H13B109.5
C14—C6—C5114.6 (3)C8—C13—H13C109.5
C7—C6—C5111.5 (3)H13A—C13—H13C109.5
C14—C6—H6105.5H13B—C13—H13C109.5
C7—C6—H6105.5C16—C14—C15121.5 (4)
C5—C6—H6105.5C16—C14—C6118.1 (4)
C6—C7—C8111.2 (3)C15—C14—C6120.3 (4)
C6—C7—H7A109.4C14—C15—H15A109.5
C8—C7—H7A109.4C14—C15—H15B109.5
C6—C7—H7B109.4H15A—C15—H15B109.5
C8—C7—H7B109.4C14—C15—H15C109.5
H7A—C7—H7B108.0H15A—C15—H15C109.5
C7—C8—C13110.8 (3)H15B—C15—H15C109.5
C7—C8—C9111.9 (3)C14—C16—H16A120.0
C13—C8—C9113.8 (3)C14—C16—H16B120.0
C7—C8—H8106.6H16A—C16—H16B120.0
C13—C8—H8106.6N1—C17—C5174.6 (4)
C10—C1—C2—O1168.8 (3)C13—C8—C9—C11162.8 (3)
C10—C1—C2—C37.9 (5)C2—C1—C10—C9165.6 (3)
O1—C2—C3—C4158.4 (3)C2—C1—C10—C59.5 (5)
C1—C2—C3—C425.0 (4)C12—C9—C10—C118.4 (5)
C2—C3—C4—C555.1 (4)C11—C9—C10—C198.1 (4)
C3—C4—C5—C1763.7 (4)C8—C9—C10—C1142.1 (3)
C3—C4—C5—C1053.4 (4)C12—C9—C10—C5166.6 (3)
C3—C4—C5—C6174.3 (3)C11—C9—C10—C576.9 (4)
C17—C5—C6—C1461.0 (4)C8—C9—C10—C542.8 (4)
C4—C5—C6—C1457.7 (4)C17—C5—C10—C195.8 (4)
C10—C5—C6—C14178.9 (3)C4—C5—C10—C121.1 (4)
C17—C5—C6—C769.4 (4)C6—C5—C10—C1141.0 (3)
C4—C5—C6—C7171.9 (3)C17—C5—C10—C979.4 (4)
C10—C5—C6—C750.7 (4)C4—C5—C10—C9163.6 (3)
C14—C6—C7—C8168.4 (3)C6—C5—C10—C943.7 (4)
C5—C6—C7—C860.6 (4)C7—C6—C14—C16115.1 (4)
C6—C7—C8—C1368.8 (4)C5—C6—C14—C16115.4 (4)
C6—C7—C8—C959.3 (4)C7—C6—C14—C1561.3 (5)
C7—C8—C9—C1048.7 (4)C5—C6—C14—C1568.1 (5)
C13—C8—C9—C1077.8 (4)C4—C5—C17—N135 (5)
C7—C8—C9—C12173.0 (3)C10—C5—C17—N184 (4)
C13—C8—C9—C1246.5 (4)C6—C5—C17—N1154 (4)
C7—C8—C9—C1170.7 (4)
 

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