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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
CCDC references: 150871; 150872
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.
Crystal data top
C17H26O3 | Dx = 1.190 Mg m−3 |
Mr = 278.38 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 6.3914 (5) Å | θ = 9.9–13.8° |
b = 9.0264 (6) Å | µ = 0.08 mm−1 |
c = 26.9292 (19) Å | T = 150 K |
V = 1553.58 (19) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.30 × 0.30 mm |
F(000) = 608 | |
Data collection top
Enraf-Nonius CAD4 diffractometer | Rint = 0.050 |
Radiation source: rotating anode | θmax = 27.5°, θmin = 1.5° |
Graphite monochromator | h = −8→0 |
ω scans | k = −11→11 |
4168 measured reflections | l = −34→0 |
2084 independent reflections | 3 standard reflections every 60 min |
1522 reflections with I > 2σ(I) | intensity decay: <1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-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 reflections | Δρmax = 0.26 e Å−3 |
184 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1 | 1.4226 (3) | 0.4390 (2) | 0.13696 (8) | 0.0351 (5) | |
O2 | 0.8862 (3) | 0.3659 (3) | 0.28360 (8) | 0.0376 (6) | |
O3 | 1.0731 (3) | 0.3217 (2) | 0.21038 (7) | 0.0262 (4) | |
C1 | 1.2368 (4) | 0.4496 (3) | 0.12845 (9) | 0.0242 (6) | |
C2 | 1.1325 (5) | 0.5985 (3) | 0.12409 (10) | 0.0260 (6) | |
H2A | 1.2401 | 0.6772 | 0.1259 | 0.031* | |
H2B | 1.0355 | 0.6122 | 0.1524 | 0.031* | |
C3 | 1.0096 (4) | 0.6145 (3) | 0.07503 (10) | 0.0246 (6) | |
H3 | 1.1129 | 0.6103 | 0.0472 | 0.029* | |
C4 | 0.8606 (4) | 0.4828 (3) | 0.06909 (10) | 0.0246 (6) | |
H4A | 0.7887 | 0.4906 | 0.0366 | 0.029* | |
H4B | 0.7526 | 0.4875 | 0.0954 | 0.029* | |
C5 | 0.9730 (4) | 0.3323 (3) | 0.07209 (9) | 0.0226 (6) | |
H5 | 0.8633 | 0.2533 | 0.0712 | 0.027* | |
C6 | 1.0980 (4) | 0.3131 (3) | 0.12141 (10) | 0.0224 (6) | |
C7 | 0.9466 (4) | 0.3109 (3) | 0.16644 (9) | 0.0211 (5) | |
H7 | 0.8522 | 0.3990 | 0.1646 | 0.025* | |
C8 | 0.8148 (5) | 0.1722 (3) | 0.17446 (10) | 0.0266 (6) | |
H8A | 0.8890 | 0.0828 | 0.1625 | 0.032* | |
H8B | 0.6788 | 0.1802 | 0.1571 | 0.032* | |
C9 | 0.7842 (4) | 0.1670 (3) | 0.23093 (10) | 0.0248 (6) | |
H9 | 0.7907 | 0.0626 | 0.2433 | 0.030* | |
C10 | 0.5907 (5) | 0.2468 (3) | 0.25177 (12) | 0.0308 (7) | |
H10A | 0.4818 | 0.2587 | 0.2259 | 0.037* | |
H10B | 0.5307 | 0.1919 | 0.2802 | 0.037* | |
C11 | 0.6756 (5) | 0.3952 (4) | 0.26799 (12) | 0.0364 (8) | |
H11A | 0.6736 | 0.4667 | 0.2401 | 0.044* | |
H11B | 0.5919 | 0.4360 | 0.2957 | 0.044* | |
C12 | 0.9681 (4) | 0.2578 (3) | 0.25116 (11) | 0.0264 (6) | |
H12 | 1.0660 | 0.1915 | 0.2697 | 0.032* | |
C13 | 1.2303 (5) | 0.1721 (3) | 0.12056 (11) | 0.0293 (7) | |
H13A | 1.1444 | 0.0888 | 0.1092 | 0.044* | |
H13B | 1.2826 | 0.1514 | 0.1541 | 0.044* | |
H13C | 1.3488 | 0.1856 | 0.0979 | 0.044* | |
C14 | 1.1154 (5) | 0.3096 (3) | 0.02692 (10) | 0.0305 (7) | |
H14A | 1.1490 | 0.2041 | 0.0236 | 0.046* | |
H14B | 1.2448 | 0.3663 | 0.0314 | 0.046* | |
H14C | 1.0433 | 0.3438 | −0.0031 | 0.046* | |
C15 | 0.8984 (5) | 0.7613 (3) | 0.07182 (11) | 0.0302 (7) | |
C16 | 0.9433 (6) | 0.8556 (4) | 0.03615 (13) | 0.0507 (10) | |
H16A | 0.8721 | 0.9478 | 0.0343 | 0.061* | |
H16B | 1.0470 | 0.8315 | 0.0122 | 0.061* | |
C17 | 0.7351 (6) | 0.7955 (4) | 0.11048 (14) | 0.0465 (9) | |
H17A | 0.8034 | 0.8127 | 0.1426 | 0.070* | |
H17B | 0.6384 | 0.7117 | 0.1133 | 0.070* | |
H17C | 0.6573 | 0.8844 | 0.1007 | 0.070* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0257 (11) | 0.0384 (12) | 0.0412 (12) | −0.0039 (11) | −0.0023 (10) | 0.0050 (10) |
O2 | 0.0344 (12) | 0.0455 (13) | 0.0328 (11) | −0.0144 (11) | 0.0036 (10) | −0.0131 (10) |
O3 | 0.0228 (10) | 0.0350 (10) | 0.0209 (9) | −0.0092 (10) | −0.0024 (8) | 0.0016 (8) |
C1 | 0.0236 (14) | 0.0334 (16) | 0.0155 (12) | −0.0011 (13) | −0.0011 (12) | 0.0049 (11) |
C2 | 0.0276 (16) | 0.0250 (14) | 0.0254 (14) | −0.0071 (13) | −0.0031 (13) | −0.0012 (11) |
C3 | 0.0266 (14) | 0.0253 (14) | 0.0217 (13) | −0.0023 (13) | 0.0020 (13) | −0.0006 (12) |
C4 | 0.0247 (14) | 0.0293 (14) | 0.0198 (12) | −0.0011 (13) | −0.0018 (12) | −0.0004 (11) |
C5 | 0.0240 (13) | 0.0220 (13) | 0.0219 (13) | −0.0030 (12) | −0.0019 (12) | −0.0019 (11) |
C6 | 0.0201 (13) | 0.0238 (13) | 0.0232 (13) | 0.0007 (13) | 0.0020 (12) | −0.0005 (11) |
C7 | 0.0209 (13) | 0.0228 (12) | 0.0196 (12) | 0.0013 (12) | −0.0024 (11) | 0.0017 (11) |
C8 | 0.0255 (14) | 0.0279 (14) | 0.0265 (14) | −0.0027 (13) | 0.0000 (12) | −0.0022 (12) |
C9 | 0.0255 (15) | 0.0183 (13) | 0.0305 (14) | −0.0002 (13) | 0.0039 (13) | 0.0039 (11) |
C10 | 0.0258 (15) | 0.0329 (16) | 0.0336 (16) | −0.0014 (15) | 0.0019 (14) | 0.0005 (14) |
C11 | 0.0373 (18) | 0.0326 (17) | 0.0395 (17) | 0.0046 (15) | 0.0114 (15) | −0.0019 (14) |
C12 | 0.0232 (15) | 0.0318 (15) | 0.0243 (13) | −0.0023 (13) | −0.0032 (13) | 0.0065 (13) |
C13 | 0.0288 (15) | 0.0268 (14) | 0.0323 (15) | 0.0057 (14) | −0.0023 (14) | 0.0001 (13) |
C14 | 0.0345 (16) | 0.0326 (15) | 0.0246 (14) | −0.0014 (16) | −0.0007 (13) | −0.0016 (12) |
C15 | 0.0344 (16) | 0.0232 (14) | 0.0329 (15) | −0.0003 (15) | −0.0112 (15) | −0.0015 (12) |
C16 | 0.066 (3) | 0.0337 (18) | 0.052 (2) | 0.003 (2) | −0.007 (2) | 0.0102 (15) |
C17 | 0.045 (2) | 0.0302 (17) | 0.064 (2) | 0.0143 (17) | 0.0049 (19) | −0.0055 (16) |
Geometric parameters (Å, º) top
O1—C1 | 1.213 (3) | C8—H8A | 0.9900 |
O2—C12 | 1.410 (4) | C8—H8B | 0.9900 |
O2—C11 | 1.435 (4) | C9—C12 | 1.533 (4) |
O3—C12 | 1.410 (3) | C9—C10 | 1.537 (4) |
O3—C7 | 1.436 (3) | C9—H9 | 1.0000 |
C1—C2 | 1.505 (4) | C10—C11 | 1.510 (4) |
C1—C6 | 1.530 (4) | C10—H10A | 0.9900 |
C2—C3 | 1.544 (4) | C10—H10B | 0.9900 |
C2—H2A | 0.9900 | C11—H11A | 0.9900 |
C2—H2B | 0.9900 | C11—H11B | 0.9900 |
C3—C15 | 1.506 (4) | C12—H12 | 1.0000 |
C3—C4 | 1.531 (4) | C13—H13A | 0.9800 |
C3—H3 | 1.0000 | C13—H13B | 0.9800 |
C4—C5 | 1.539 (4) | C13—H13C | 0.9800 |
C4—H4A | 0.9900 | C14—H14A | 0.9800 |
C4—H4B | 0.9900 | C14—H14B | 0.9800 |
C5—C14 | 1.533 (4) | C14—H14C | 0.9800 |
C5—C6 | 1.560 (4) | C15—C16 | 1.315 (4) |
C5—H5 | 1.0000 | C15—C17 | 1.506 (5) |
C6—C13 | 1.528 (4) | C16—H16A | 0.9500 |
C6—C7 | 1.551 (4) | C16—H16B | 0.9500 |
C7—C8 | 1.524 (4) | C17—H17A | 0.9800 |
C7—H7 | 1.0000 | C17—H17B | 0.9800 |
C8—C9 | 1.534 (4) | C17—H17C | 0.9800 |
| | | |
C12—O2—C11 | 107.1 (2) | C8—C9—C10 | 116.8 (2) |
C12—O3—C7 | 110.2 (2) | C12—C9—C10 | 103.7 (2) |
O1—C1—C2 | 121.3 (3) | C8—C9—H9 | 110.7 |
O1—C1—C6 | 121.8 (3) | C12—C9—H9 | 110.7 |
C2—C1—C6 | 116.9 (2) | C10—C9—H9 | 110.7 |
C1—C2—C3 | 112.1 (2) | C11—C10—C9 | 103.4 (2) |
C1—C2—H2A | 109.2 | C11—C10—H10A | 111.1 |
C3—C2—H2A | 109.2 | C9—C10—H10A | 111.1 |
C1—C2—H2B | 109.2 | C11—C10—H10B | 111.1 |
C3—C2—H2B | 109.2 | C9—C10—H10B | 111.1 |
H2A—C2—H2B | 107.9 | H10A—C10—H10B | 109.0 |
C15—C3—C4 | 112.6 (2) | O2—C11—C10 | 104.9 (3) |
C15—C3—C2 | 111.8 (2) | O2—C11—H11A | 110.8 |
C4—C3—C2 | 109.5 (2) | C10—C11—H11A | 110.8 |
C15—C3—H3 | 107.6 | O2—C11—H11B | 110.8 |
C4—C3—H3 | 107.6 | C10—C11—H11B | 110.8 |
C2—C3—H3 | 107.6 | H11A—C11—H11B | 108.8 |
C3—C4—C5 | 112.9 (2) | O2—C12—O3 | 112.1 (2) |
C3—C4—H4A | 109.0 | O2—C12—C9 | 107.8 (2) |
C5—C4—H4A | 109.0 | O3—C12—C9 | 107.9 (2) |
C3—C4—H4B | 109.0 | O2—C12—H12 | 109.7 |
C5—C4—H4B | 109.0 | O3—C12—H12 | 109.7 |
H4A—C4—H4B | 107.8 | C9—C12—H12 | 109.7 |
C14—C5—C4 | 110.7 (2) | C6—C13—H13A | 109.5 |
C14—C5—C6 | 110.9 (2) | C6—C13—H13B | 109.5 |
C4—C5—C6 | 112.5 (2) | H13A—C13—H13B | 109.5 |
C14—C5—H5 | 107.5 | C6—C13—H13C | 109.5 |
C4—C5—H5 | 107.5 | H13A—C13—H13C | 109.5 |
C6—C5—H5 | 107.5 | H13B—C13—H13C | 109.5 |
C13—C6—C1 | 110.6 (2) | C5—C14—H14A | 109.5 |
C13—C6—C7 | 110.2 (2) | C5—C14—H14B | 109.5 |
C1—C6—C7 | 106.0 (2) | H14A—C14—H14B | 109.5 |
C13—C6—C5 | 111.3 (2) | C5—C14—H14C | 109.5 |
C1—C6—C5 | 108.2 (2) | H14A—C14—H14C | 109.5 |
C7—C6—C5 | 110.3 (2) | H14B—C14—H14C | 109.5 |
O3—C7—C8 | 104.5 (2) | C16—C15—C17 | 121.6 (3) |
O3—C7—C6 | 107.0 (2) | C16—C15—C3 | 120.5 (3) |
C8—C7—C6 | 117.8 (2) | C17—C15—C3 | 117.9 (3) |
O3—C7—H7 | 109.1 | C15—C16—H16A | 120.0 |
C8—C7—H7 | 109.1 | C15—C16—H16B | 120.0 |
C6—C7—H7 | 109.1 | H16A—C16—H16B | 120.0 |
C7—C8—C9 | 103.7 (2) | C15—C17—H17A | 109.5 |
C7—C8—H8A | 111.0 | C15—C17—H17B | 109.5 |
C9—C8—H8A | 111.0 | H17A—C17—H17B | 109.5 |
C7—C8—H8B | 111.0 | C15—C17—H17C | 109.5 |
C9—C8—H8B | 111.0 | H17A—C17—H17C | 109.5 |
H8A—C8—H8B | 109.0 | H17B—C17—H17C | 109.5 |
C8—C9—C12 | 103.8 (2) | | |
| | | |
O1—C1—C2—C3 | 126.6 (3) | C5—C6—C7—O3 | −169.1 (2) |
C6—C1—C2—C3 | −53.1 (3) | C13—C6—C7—C8 | −49.7 (3) |
C1—C2—C3—C15 | 177.7 (2) | C1—C6—C7—C8 | −169.4 (2) |
C1—C2—C3—C4 | 52.3 (3) | C5—C6—C7—C8 | 73.7 (3) |
C15—C3—C4—C5 | 179.7 (2) | O3—C7—C8—C9 | 31.5 (3) |
C2—C3—C4—C5 | −55.3 (3) | C6—C7—C8—C9 | 150.0 (2) |
C3—C4—C5—C14 | −68.2 (3) | C7—C8—C9—C12 | −23.0 (3) |
C3—C4—C5—C6 | 56.5 (3) | C7—C8—C9—C10 | 90.3 (3) |
O1—C1—C6—C13 | −6.7 (4) | C8—C9—C10—C11 | −97.2 (3) |
C2—C1—C6—C13 | 173.0 (2) | C12—C9—C10—C11 | 16.2 (3) |
O1—C1—C6—C7 | 112.8 (3) | C12—O2—C11—C10 | 37.2 (3) |
C2—C1—C6—C7 | −67.5 (3) | C9—C10—C11—O2 | −32.3 (3) |
O1—C1—C6—C5 | −128.8 (3) | C11—O2—C12—O3 | 92.1 (3) |
C2—C1—C6—C5 | 50.9 (3) | C11—O2—C12—C9 | −26.5 (3) |
C14—C5—C6—C13 | −48.1 (3) | C7—O3—C12—O2 | −104.6 (3) |
C4—C5—C6—C13 | −172.7 (2) | C7—O3—C12—C9 | 13.9 (3) |
C14—C5—C6—C1 | 73.7 (3) | C8—C9—C12—O2 | 127.9 (2) |
C4—C5—C6—C1 | −50.9 (3) | C10—C9—C12—O2 | 5.4 (3) |
C14—C5—C6—C7 | −170.8 (2) | C8—C9—C12—O3 | 6.6 (3) |
C4—C5—C6—C7 | 64.6 (3) | C10—C9—C12—O3 | −115.8 (2) |
C12—O3—C7—C8 | −28.8 (3) | C4—C3—C15—C16 | −117.5 (3) |
C12—O3—C7—C6 | −154.5 (2) | C2—C3—C15—C16 | 118.9 (3) |
C13—C6—C7—O3 | 67.5 (3) | C4—C3—C15—C17 | 62.3 (3) |
C1—C6—C7—O3 | −52.2 (3) | C2—C3—C15—C17 | −61.3 (3) |
Crystal data top
C17H23NO | Dx = 1.148 Mg m−3 |
Mr = 257.36 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 8.3419 (9) Å | θ = 9.9–15.1° |
b = 12.3902 (10) Å | µ = 0.07 mm−1 |
c = 14.4052 (14) Å | T = 150 K |
V = 1488.9 (2) Å3 | Block, yellow |
Z = 4 | 0.30 × 0.30 × 0.30 mm |
F(000) = 560 | |
Data collection top
Enraf-Nonius CAD4T diffractometer | Rint = 0.100 |
Radiation source: rotating anode | θmax = 25.0°, θmin = 2.2° |
Graphite monochromator | h = 0→9 |
ω scans | k = −14→14 |
5872 measured reflections | l = −17→17 |
1534 independent reflections | 3 standard reflections every 60 min |
1059 reflections with I > 2σ(I) | intensity decay: <1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-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 reflections | Δρmax = 0.16 e Å−3 |
176 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.0718 (4) | 0.2874 (2) | −0.02667 (17) | 0.0422 (8) | |
N1 | −0.0928 (4) | 0.6141 (2) | 0.1741 (3) | 0.0426 (10) | |
C1 | 0.2051 (5) | 0.3654 (3) | 0.0995 (3) | 0.0291 (10) | |
H1 | 0.3065 | 0.3494 | 0.0727 | 0.035* | |
C2 | 0.0615 (5) | 0.3249 (3) | 0.0515 (2) | 0.0278 (9) | |
C3 | −0.0963 (5) | 0.3372 (3) | 0.0999 (3) | 0.0278 (9) | |
H3A | −0.1658 | 0.2748 | 0.0848 | 0.033* | |
H3B | −0.1502 | 0.4035 | 0.0775 | 0.033* | |
C4 | −0.0739 (5) | 0.3439 (3) | 0.2040 (2) | 0.0245 (9) | |
H4A | −0.0322 | 0.2742 | 0.2272 | 0.029* | |
H4B | −0.1791 | 0.3570 | 0.2338 | 0.029* | |
C5 | 0.0430 (4) | 0.4350 (3) | 0.2313 (2) | 0.0225 (9) | |
C6 | 0.0728 (4) | 0.4289 (3) | 0.3377 (2) | 0.0274 (9) | |
H6 | 0.1159 | 0.3549 | 0.3494 | 0.033* | |
C7 | 0.2049 (4) | 0.5060 (3) | 0.3678 (3) | 0.0328 (10) | |
H7A | 0.2187 | 0.5016 | 0.4359 | 0.039* | |
H7B | 0.1736 | 0.5809 | 0.3520 | 0.039* | |
C8 | 0.3636 (5) | 0.4789 (3) | 0.3202 (3) | 0.0332 (10) | |
H8 | 0.4417 | 0.5360 | 0.3392 | 0.040* | |
C9 | 0.3499 (4) | 0.4849 (3) | 0.2131 (3) | 0.0262 (9) | |
C10 | 0.2034 (4) | 0.4232 (3) | 0.1781 (3) | 0.0235 (9) | |
C11 | 0.3324 (5) | 0.6045 (3) | 0.1839 (3) | 0.0399 (11) | |
H11A | 0.4317 | 0.6434 | 0.1981 | 0.060* | |
H11B | 0.2432 | 0.6374 | 0.2179 | 0.060* | |
H11C | 0.3113 | 0.6086 | 0.1170 | 0.060* | |
C12 | 0.5044 (4) | 0.4439 (3) | 0.1675 (3) | 0.0396 (11) | |
H12A | 0.5115 | 0.3655 | 0.1749 | 0.059* | |
H12B | 0.5971 | 0.4781 | 0.1972 | 0.059* | |
H12C | 0.5033 | 0.4621 | 0.1013 | 0.059* | |
C13 | 0.4303 (5) | 0.3714 (3) | 0.3559 (3) | 0.0483 (12) | |
H13A | 0.4245 | 0.3699 | 0.4238 | 0.073* | |
H13B | 0.5422 | 0.3638 | 0.3363 | 0.073* | |
H13C | 0.3669 | 0.3118 | 0.3304 | 0.073* | |
C14 | −0.0777 (5) | 0.4374 (4) | 0.3966 (3) | 0.0425 (11) | |
C15 | −0.1657 (6) | 0.5369 (4) | 0.4007 (3) | 0.0586 (14) | |
H15A | −0.2609 | 0.5273 | 0.4397 | 0.088* | |
H15B | −0.1987 | 0.5579 | 0.3380 | 0.088* | |
H15C | −0.0976 | 0.5935 | 0.4273 | 0.088* | |
C16 | −0.1212 (6) | 0.3492 (4) | 0.4495 (3) | 0.0579 (14) | |
H16A | −0.2112 | 0.3535 | 0.4897 | 0.070* | |
H16B | −0.0612 | 0.2842 | 0.4456 | 0.070* | |
C17 | −0.0307 (4) | 0.5382 (3) | 0.2024 (3) | 0.0282 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0486 (18) | 0.0500 (18) | 0.0281 (16) | 0.0001 (15) | 0.0006 (17) | −0.0145 (14) |
N1 | 0.034 (2) | 0.0274 (18) | 0.067 (3) | 0.0033 (17) | −0.008 (2) | −0.0054 (19) |
C1 | 0.027 (2) | 0.030 (2) | 0.030 (2) | 0.0013 (19) | 0.002 (2) | −0.0022 (18) |
C2 | 0.039 (2) | 0.021 (2) | 0.023 (2) | 0.0038 (19) | 0.002 (2) | −0.0001 (16) |
C3 | 0.029 (2) | 0.027 (2) | 0.027 (2) | 0.0020 (19) | −0.004 (2) | −0.0041 (17) |
C4 | 0.023 (2) | 0.0235 (18) | 0.027 (2) | −0.0011 (16) | 0.002 (2) | −0.0018 (15) |
C5 | 0.025 (2) | 0.0195 (18) | 0.0232 (19) | −0.0019 (16) | 0.0015 (18) | −0.0014 (16) |
C6 | 0.027 (2) | 0.033 (2) | 0.022 (2) | 0.0012 (18) | 0.001 (2) | −0.0059 (18) |
C7 | 0.033 (2) | 0.036 (2) | 0.029 (2) | −0.005 (2) | −0.002 (2) | −0.0086 (18) |
C8 | 0.029 (2) | 0.034 (2) | 0.036 (2) | −0.0057 (19) | −0.004 (2) | −0.0072 (19) |
C9 | 0.019 (2) | 0.026 (2) | 0.033 (2) | 0.0001 (16) | 0.000 (2) | −0.0027 (17) |
C10 | 0.024 (2) | 0.0182 (19) | 0.028 (2) | 0.0020 (16) | −0.0033 (19) | 0.0037 (17) |
C11 | 0.036 (2) | 0.035 (2) | 0.049 (3) | −0.008 (2) | −0.003 (2) | 0.005 (2) |
C12 | 0.024 (2) | 0.046 (2) | 0.048 (3) | −0.001 (2) | 0.002 (2) | −0.008 (2) |
C13 | 0.035 (2) | 0.056 (3) | 0.054 (3) | 0.003 (2) | −0.013 (3) | 0.013 (2) |
C14 | 0.036 (3) | 0.066 (3) | 0.025 (2) | −0.013 (2) | −0.001 (2) | −0.017 (2) |
C15 | 0.048 (3) | 0.080 (4) | 0.048 (3) | 0.011 (3) | 0.009 (3) | −0.025 (3) |
C16 | 0.058 (3) | 0.073 (3) | 0.043 (3) | −0.015 (3) | 0.016 (3) | 0.003 (3) |
C17 | 0.024 (2) | 0.026 (2) | 0.034 (2) | 0.0033 (18) | −0.001 (2) | −0.0068 (18) |
Geometric parameters (Å, º) top
O1—C2 | 1.222 (4) | C8—C9 | 1.548 (6) |
N1—C17 | 1.148 (4) | C8—H8 | 1.0000 |
C1—C10 | 1.341 (5) | C9—C10 | 1.527 (5) |
C1—C2 | 1.471 (5) | C9—C12 | 1.533 (5) |
C1—H1 | 0.9500 | C9—C11 | 1.548 (5) |
C2—C3 | 1.497 (5) | C11—H11A | 0.9800 |
C3—C4 | 1.514 (5) | C11—H11B | 0.9800 |
C3—H3A | 0.9900 | C11—H11C | 0.9800 |
C3—H3B | 0.9900 | C12—H12A | 0.9800 |
C4—C5 | 1.542 (5) | C12—H12B | 0.9800 |
C4—H4A | 0.9900 | C12—H12C | 0.9800 |
C4—H4B | 0.9900 | C13—H13A | 0.9800 |
C5—C17 | 1.479 (5) | C13—H13B | 0.9800 |
C5—C10 | 1.549 (5) | C13—H13C | 0.9800 |
C5—C6 | 1.555 (5) | C14—C16 | 1.381 (6) |
C6—C14 | 1.519 (5) | C14—C15 | 1.436 (6) |
C6—C7 | 1.521 (5) | C15—H15A | 0.9800 |
C6—H6 | 1.0000 | C15—H15B | 0.9800 |
C7—C8 | 1.528 (5) | C15—H15C | 0.9800 |
C7—H7A | 0.9900 | C16—H16A | 0.9500 |
C7—H7B | 0.9900 | C16—H16B | 0.9500 |
C8—C13 | 1.532 (5) | | |
| | | |
C10—C1—C2 | 124.8 (4) | C9—C8—H8 | 106.6 |
C10—C1—H1 | 117.6 | C10—C9—C12 | 111.4 (3) |
C2—C1—H1 | 117.6 | C10—C9—C11 | 108.3 (3) |
O1—C2—C1 | 120.4 (4) | C12—C9—C11 | 106.2 (3) |
O1—C2—C3 | 122.0 (4) | C10—C9—C8 | 111.3 (3) |
C1—C2—C3 | 117.6 (3) | C12—C9—C8 | 110.4 (3) |
C2—C3—C4 | 111.0 (3) | C11—C9—C8 | 108.9 (3) |
C2—C3—H3A | 109.4 | C1—C10—C9 | 122.5 (3) |
C4—C3—H3A | 109.4 | C1—C10—C5 | 118.5 (3) |
C2—C3—H3B | 109.4 | C9—C10—C5 | 118.8 (3) |
C4—C3—H3B | 109.4 | C9—C11—H11A | 109.5 |
H3A—C3—H3B | 108.0 | C9—C11—H11B | 109.5 |
C3—C4—C5 | 111.8 (3) | H11A—C11—H11B | 109.5 |
C3—C4—H4A | 109.3 | C9—C11—H11C | 109.5 |
C5—C4—H4A | 109.3 | H11A—C11—H11C | 109.5 |
C3—C4—H4B | 109.3 | H11B—C11—H11C | 109.5 |
C5—C4—H4B | 109.3 | C9—C12—H12A | 109.5 |
H4A—C4—H4B | 107.9 | C9—C12—H12B | 109.5 |
C17—C5—C4 | 107.4 (3) | H12A—C12—H12B | 109.5 |
C17—C5—C10 | 107.6 (3) | C9—C12—H12C | 109.5 |
C4—C5—C10 | 110.6 (3) | H12A—C12—H12C | 109.5 |
C17—C5—C6 | 112.7 (3) | H12B—C12—H12C | 109.5 |
C4—C5—C6 | 108.5 (3) | C8—C13—H13A | 109.5 |
C10—C5—C6 | 110.2 (3) | C8—C13—H13B | 109.5 |
C14—C6—C7 | 113.4 (3) | H13A—C13—H13B | 109.5 |
C14—C6—C5 | 114.6 (3) | C8—C13—H13C | 109.5 |
C7—C6—C5 | 111.5 (3) | H13A—C13—H13C | 109.5 |
C14—C6—H6 | 105.5 | H13B—C13—H13C | 109.5 |
C7—C6—H6 | 105.5 | C16—C14—C15 | 121.5 (4) |
C5—C6—H6 | 105.5 | C16—C14—C6 | 118.1 (4) |
C6—C7—C8 | 111.2 (3) | C15—C14—C6 | 120.3 (4) |
C6—C7—H7A | 109.4 | C14—C15—H15A | 109.5 |
C8—C7—H7A | 109.4 | C14—C15—H15B | 109.5 |
C6—C7—H7B | 109.4 | H15A—C15—H15B | 109.5 |
C8—C7—H7B | 109.4 | C14—C15—H15C | 109.5 |
H7A—C7—H7B | 108.0 | H15A—C15—H15C | 109.5 |
C7—C8—C13 | 110.8 (3) | H15B—C15—H15C | 109.5 |
C7—C8—C9 | 111.9 (3) | C14—C16—H16A | 120.0 |
C13—C8—C9 | 113.8 (3) | C14—C16—H16B | 120.0 |
C7—C8—H8 | 106.6 | H16A—C16—H16B | 120.0 |
C13—C8—H8 | 106.6 | N1—C17—C5 | 174.6 (4) |
| | | |
C10—C1—C2—O1 | 168.8 (3) | C13—C8—C9—C11 | −162.8 (3) |
C10—C1—C2—C3 | −7.9 (5) | C2—C1—C10—C9 | −165.6 (3) |
O1—C2—C3—C4 | 158.4 (3) | C2—C1—C10—C5 | 9.5 (5) |
C1—C2—C3—C4 | −25.0 (4) | C12—C9—C10—C1 | −18.4 (5) |
C2—C3—C4—C5 | 55.1 (4) | C11—C9—C10—C1 | 98.1 (4) |
C3—C4—C5—C17 | 63.7 (4) | C8—C9—C10—C1 | −142.1 (3) |
C3—C4—C5—C10 | −53.4 (4) | C12—C9—C10—C5 | 166.6 (3) |
C3—C4—C5—C6 | −174.3 (3) | C11—C9—C10—C5 | −76.9 (4) |
C17—C5—C6—C14 | 61.0 (4) | C8—C9—C10—C5 | 42.8 (4) |
C4—C5—C6—C14 | −57.7 (4) | C17—C5—C10—C1 | −95.8 (4) |
C10—C5—C6—C14 | −178.9 (3) | C4—C5—C10—C1 | 21.1 (4) |
C17—C5—C6—C7 | −69.4 (4) | C6—C5—C10—C1 | 141.0 (3) |
C4—C5—C6—C7 | 171.9 (3) | C17—C5—C10—C9 | 79.4 (4) |
C10—C5—C6—C7 | 50.7 (4) | C4—C5—C10—C9 | −163.6 (3) |
C14—C6—C7—C8 | 168.4 (3) | C6—C5—C10—C9 | −43.7 (4) |
C5—C6—C7—C8 | −60.6 (4) | C7—C6—C14—C16 | −115.1 (4) |
C6—C7—C8—C13 | −68.8 (4) | C5—C6—C14—C16 | 115.4 (4) |
C6—C7—C8—C9 | 59.3 (4) | C7—C6—C14—C15 | 61.3 (5) |
C7—C8—C9—C10 | −48.7 (4) | C5—C6—C14—C15 | −68.1 (5) |
C13—C8—C9—C10 | 77.8 (4) | C4—C5—C17—N1 | −35 (5) |
C7—C8—C9—C12 | −173.0 (3) | C10—C5—C17—N1 | 84 (4) |
C13—C8—C9—C12 | −46.5 (4) | C6—C5—C17—N1 | −154 (4) |
C7—C8—C9—C11 | 70.7 (4) | | |
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