(2R,3R,5R)-2-[(2R,3aS,6aR)-2,3,3a,4,5,6a-Hexa­hydro­furo­[2,3-b]­furan-2-yl]-5-isoprop­en­yl-2,3-di­methyl­cyclo­hexanone and (4aR,5S,7R)-5-isopropenyl-7,8,8-tri­methyl-2,3,4,4a,5,6,7,8-octa­hydro­naphthalene-4a-carbo­nitrile

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.

Computing details

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)

Crystal data

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) Å^3	Block, colourless
Z = 4	0.50 × 0.30 × 0.30 mm
F(000) = 608

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0559P)^2 + 0.1569P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(II)

Crystal data

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) Å^3	Block, yellow
Z = 4	0.30 × 0.30 × 0.30 mm
F(000) = 560

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0418P)^2 + 0.0185P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)