(±)-2'-Phenyl-cyclo-hexa-nespiro-4'-(aze-pano[1,2-b]isoxazolidine).

In the crystal structure of the racemic title isoxazolidine, C(19)H(27)NO, the relative stereochemistry between the phenyl group and the bridgehead H atom is shown to be syn. There are two mol-ecules in the asymmetric unit, one of which is the 7R*,13R* enanti-omer, and one of which is the 7S*,13S* enanti-omer. These enanti-omers adopt different orientations of the phenyl ring with respect to the isoxazolidine ring, with C-C-C-C torsion angles of 63.6 (4) and 86.8 (4)°, respectively. In both enanti-omers, the six-membered ring adopts a chair conformation, while the seven-membered ring adopts a twist-chair conformation.

Related literature

For related literature regarding the synthesis towards the spiro­imine unit of the spiro­lides, see: Brimble & Trzoss (2004 ▶); Brimble et al. (2005 ▶); O’Connor et al. (2008 ▶). For the crystal structure of the related 7,6-spiro­lactam unit, see: Guéret et al. (2008 ▶). For isolation of spiro­lides from natural resources, see: Hu et al. (2001 ▶); MacKinnon et al. (2006 ▶); Ciminiello et al. (2007 ▶).

Experimental

Crystal data

C19H27NO

M = 285.42

Triclinic,

a = 9.8516 (1) Å

b = 10.4560 (1) Å

c = 16.0957 (1) Å

α = 101.058 (1)°

β = 92.833 (1)°

γ = 96.527 (1)°

V = 1612.34 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 85 (2) K

0.32 × 0.24 × 0.22 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.985

15138 measured reflections

6437 independent reflections

4959 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.194

S = 1.06

6437 reflections

379 parameters

H-atom parameters constrained

Δρmax = 1.21 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Siemens, 1995 ▶); cell refinement: SAINT (Siemens, 1995 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021867/bi2294sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021867/bi2294Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H27NO	Z = 4
Mr = 285.42	F000 = 624
Triclinic, P1	Dx = 1.176 Mg m−3
Hall symbol: -P 1	Melting point: 338.8(7) K
a = 9.8516 (1) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.4560 (1) Å	Cell parameters from 6437 reflections
c = 16.0957 (1) Å	θ = 1.3–26.4º
α = 101.058 (1)º	µ = 0.07 mm−1
β = 92.833 (1)º	T = 85 (2) K
γ = 96.527 (1)º	Needles, white
V = 1612.34 (2) Å3	0.32 × 0.24 × 0.22 mm

Siemens SMART CCD diffractometer	6437 independent reflections
Radiation source: fine-focus sealed tube	4959 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 85(2) K	θmax = 26.4º
ω scans	θmin = 1.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.978, Tmax = 0.985	k = −13→12
15138 measured reflections	l = 0→20

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)] = 0.084	H-atom parameters constrained
wR(F2) = 0.194	w = 1/[σ2(Fo2) + (0.0475P)2 + 4.1372P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
6437 reflections	Δρmax = 1.21 e Å−3
379 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
O	0.6455 (2)	0.6154 (2)	0.33169 (13)	0.0268 (5)
N	0.6590 (3)	0.5526 (3)	0.24237 (15)	0.0226 (6)
C1	0.8405 (3)	0.4282 (3)	0.17312 (17)	0.0161 (6)
C2	0.9653 (3)	0.5340 (3)	0.1897 (2)	0.0243 (7)
H2A	0.9346	0.6189	0.1894	0.029*
H2B	1.0085	0.5368	0.2456	0.029*
C3	1.0710 (3)	0.5099 (3)	0.1238 (2)	0.0303 (7)
H3A	1.0313	0.5166	0.0687	0.036*
H3B	1.1496	0.5768	0.1390	0.036*
C4	1.1179 (3)	0.3742 (3)	0.1186 (2)	0.0347 (8)
H4A	1.1678	0.3714	0.1715	0.042*
H4B	1.1796	0.3592	0.0735	0.042*
C5	0.9964 (3)	0.2656 (3)	0.1013 (2)	0.0319 (8)
H5A	1.0288	0.1820	0.1033	0.038*
H5B	0.9542	0.2603	0.0448	0.038*
C6	0.8892 (3)	0.2914 (3)	0.1667 (2)	0.0252 (7)
H6A	0.9280	0.2842	0.2219	0.030*
H6B	0.8107	0.2245	0.1511	0.030*
C7	0.7425 (3)	0.4433 (3)	0.24678 (18)	0.0219 (6)
H7A	0.6798	0.3616	0.2397	0.026*
C8	0.5176 (3)	0.5018 (3)	0.20965 (18)	0.0213 (6)
H8A	0.4585	0.5690	0.2264	0.026*
H8B	0.4865	0.4267	0.2341	0.026*
C9	0.5073 (3)	0.4610 (3)	0.11317 (18)	0.0229 (6)
H9A	0.4157	0.4169	0.0949	0.028*
H9B	0.5186	0.5399	0.0896	0.028*
C10	0.6094 (3)	0.3717 (3)	0.07546 (19)	0.0238 (7)
H10A	0.5858	0.3437	0.0150	0.029*
H10B	0.6010	0.2939	0.1003	0.029*
C11	0.7593 (3)	0.4353 (3)	0.08922 (18)	0.0228 (6)
H11A	0.7609	0.5272	0.0861	0.027*
H11B	0.8080	0.3946	0.0423	0.027*
C12	0.8092 (3)	0.4744 (3)	0.33864 (19)	0.0249 (7)
H12A	0.7685	0.4139	0.3719	0.030*
H12B	0.9071	0.4705	0.3393	0.030*
C13	0.7780 (3)	0.6141 (3)	0.37195 (19)	0.0239 (7)
H13A	0.8452	0.6775	0.3535	0.029*
C14	0.7717 (3)	0.6482 (3)	0.46735 (19)	0.0254 (7)
C15	0.8925 (3)	0.6960 (3)	0.51785 (19)	0.0275 (7)
H15A	0.9748	0.7075	0.4926	0.033*
C16	0.8910 (3)	0.7266 (3)	0.60540 (19)	0.0271 (7)
H16A	0.9722	0.7578	0.6387	0.033*
C17	0.7693 (4)	0.7109 (3)	0.6432 (2)	0.0324 (8)
H17A	0.7683	0.7323	0.7020	0.039*
C18	0.6486 (4)	0.6633 (4)	0.5938 (2)	0.0414 (9)
H18A	0.5666	0.6529	0.6194	0.050*
C19	0.6496 (3)	0.6311 (4)	0.5058 (2)	0.0333 (8)
H19A	0.5685	0.5981	0.4728	0.040*
O'	0.8141 (2)	0.0639 (2)	0.33601 (12)	0.0231 (5)
N'	0.7585 (2)	0.0078 (2)	0.24822 (14)	0.0186 (5)
C1'	0.5197 (3)	−0.0548 (3)	0.18622 (17)	0.0159 (6)
C2'	0.4734 (3)	0.0835 (3)	0.20648 (17)	0.0172 (6)
H2'A	0.4426	0.0989	0.2634	0.021*
H2'B	0.5512	0.1487	0.2051	0.021*
C3'	0.3578 (3)	0.1009 (3)	0.14386 (18)	0.0210 (6)
H3'A	0.3322	0.1888	0.1592	0.025*
H3'B	0.3892	0.0898	0.0870	0.025*
C4'	0.2331 (3)	−0.0004 (3)	0.1454 (2)	0.0250 (7)
H4'A	0.1980	0.0148	0.2012	0.030*
H4'B	0.1614	0.0096	0.1045	0.030*
C5'	0.2713 (3)	−0.1402 (3)	0.1242 (2)	0.0234 (6)
H5'A	0.2940	−0.1593	0.0655	0.028*
H5'B	0.1930	−0.2019	0.1304	0.028*
C6'	0.3936 (3)	−0.1592 (3)	0.18186 (19)	0.0190 (6)
H6'A	0.4205	−0.2454	0.1615	0.023*
H6'B	0.3644	−0.1569	0.2387	0.023*
C7'	0.6255 (3)	−0.0735 (3)	0.25610 (17)	0.0161 (6)
H7'A	0.6404	−0.1661	0.2461	0.019*
C8'	0.8619 (3)	−0.0742 (3)	0.21325 (19)	0.0227 (6)
H8'A	0.8582	−0.1516	0.2384	0.027*
H8'B	0.9525	−0.0253	0.2272	0.027*
C9'	0.8360 (3)	−0.1158 (3)	0.11659 (18)	0.0221 (6)
H9'A	0.8963	−0.1805	0.0965	0.027*
H9'B	0.8611	−0.0398	0.0916	0.027*
C10'	0.6885 (3)	−0.1737 (3)	0.08409 (18)	0.0196 (6)
H10C	0.6601	−0.2454	0.1122	0.024*
H10D	0.6863	−0.2095	0.0237	0.024*
C11'	0.5856 (3)	−0.0725 (3)	0.09918 (17)	0.0181 (6)
H11C	0.5124	−0.0976	0.0544	0.022*
H11D	0.6319	0.0121	0.0936	0.022*
C12'	0.5939 (3)	−0.0310 (3)	0.34989 (18)	0.0207 (6)
H12C	0.5004	−0.0109	0.3543	0.025*
H12D	0.6083	−0.0987	0.3818	0.025*
C13'	0.6976 (4)	0.0927 (4)	0.3809 (2)	0.0321 (8)
H13B	0.6620	0.1689	0.3646	0.039*
C14'	0.7431 (3)	0.1240 (3)	0.47534 (19)	0.0287 (7)
C15'	0.8144 (4)	0.0435 (4)	0.5145 (2)	0.0370 (8)
H15B	0.8305	−0.0371	0.4832	0.044*
C16'	0.8617 (4)	0.0779 (4)	0.5967 (3)	0.0420 (9)
H16B	0.9115	0.0222	0.6209	0.050*
C17'	0.8369 (4)	0.1928 (4)	0.6440 (2)	0.0367 (9)
H17B	0.8691	0.2142	0.7009	0.044*
C18'	0.7657 (4)	0.2789 (4)	0.6110 (2)	0.0399 (9)
H18B	0.7493	0.3575	0.6449	0.048*
C19'	0.7168 (4)	0.2452 (4)	0.5227 (2)	0.0374 (9)
H19B	0.6693	0.3018	0.4979	0.045*

	U11	U22	U33	U12	U13	U23
O	0.0293 (12)	0.0325 (12)	0.0177 (11)	0.0086 (10)	0.0025 (9)	−0.0005 (9)
N	0.0224 (13)	0.0262 (14)	0.0178 (12)	0.0041 (10)	0.0022 (10)	0.0001 (10)
C1	0.0192 (14)	0.0138 (13)	0.0145 (13)	0.0037 (11)	0.0001 (11)	0.0005 (10)
C2	0.0219 (15)	0.0196 (15)	0.0301 (17)	−0.0010 (12)	−0.0013 (13)	0.0046 (12)
C3	0.0240 (16)	0.0380 (19)	0.0284 (17)	−0.0063 (14)	−0.0009 (13)	0.0120 (14)
C4	0.0202 (16)	0.042 (2)	0.0372 (19)	0.0034 (14)	0.0091 (14)	−0.0053 (16)
C5	0.0310 (18)	0.0240 (17)	0.040 (2)	0.0096 (14)	0.0065 (15)	0.0000 (14)
C6	0.0241 (16)	0.0220 (16)	0.0305 (17)	0.0053 (12)	0.0016 (13)	0.0066 (13)
C7	0.0270 (16)	0.0177 (14)	0.0201 (15)	0.0011 (12)	0.0006 (12)	0.0024 (11)
C8	0.0174 (14)	0.0245 (15)	0.0220 (15)	0.0021 (12)	0.0010 (12)	0.0048 (12)
C9	0.0191 (15)	0.0273 (16)	0.0207 (15)	−0.0011 (12)	−0.0024 (12)	0.0041 (12)
C10	0.0263 (16)	0.0249 (16)	0.0183 (15)	0.0028 (13)	−0.0030 (12)	0.0007 (12)
C11	0.0240 (16)	0.0260 (16)	0.0176 (14)	0.0020 (12)	0.0030 (12)	0.0024 (12)
C12	0.0262 (16)	0.0267 (16)	0.0215 (15)	0.0017 (13)	−0.0001 (12)	0.0057 (12)
C13	0.0226 (15)	0.0272 (16)	0.0211 (15)	0.0014 (13)	0.0016 (12)	0.0037 (12)
C14	0.0248 (16)	0.0300 (17)	0.0189 (15)	0.0024 (13)	0.0021 (12)	−0.0007 (13)
C15	0.0239 (16)	0.0377 (19)	0.0204 (15)	0.0019 (14)	0.0027 (12)	0.0052 (13)
C16	0.0330 (18)	0.0259 (16)	0.0204 (15)	0.0001 (13)	−0.0059 (13)	0.0034 (12)
C17	0.043 (2)	0.0352 (19)	0.0162 (15)	0.0062 (15)	0.0028 (14)	−0.0023 (13)
C18	0.0274 (18)	0.068 (3)	0.0247 (18)	0.0012 (17)	0.0085 (14)	0.0000 (17)
C19	0.0243 (17)	0.050 (2)	0.0194 (16)	−0.0016 (15)	0.0021 (13)	−0.0039 (15)
O'	0.0212 (11)	0.0300 (12)	0.0135 (10)	−0.0037 (9)	−0.0021 (8)	−0.0023 (8)
N'	0.0180 (12)	0.0218 (13)	0.0128 (11)	−0.0035 (10)	−0.0024 (9)	0.0001 (9)
C1'	0.0177 (14)	0.0144 (13)	0.0136 (13)	−0.0011 (11)	0.0004 (11)	0.0002 (10)
C2'	0.0204 (14)	0.0150 (14)	0.0152 (13)	0.0010 (11)	0.0024 (11)	0.0013 (10)
C3'	0.0253 (15)	0.0190 (15)	0.0193 (14)	0.0073 (12)	0.0020 (12)	0.0027 (11)
C4'	0.0186 (15)	0.0265 (16)	0.0295 (17)	0.0065 (12)	−0.0008 (12)	0.0030 (13)
C5'	0.0167 (14)	0.0229 (16)	0.0276 (16)	−0.0021 (12)	−0.0034 (12)	0.0018 (12)
C6'	0.0171 (14)	0.0162 (14)	0.0227 (15)	−0.0008 (11)	0.0004 (11)	0.0032 (11)
C7'	0.0164 (14)	0.0135 (13)	0.0179 (14)	−0.0001 (10)	0.0021 (11)	0.0030 (10)
C8'	0.0166 (14)	0.0283 (16)	0.0217 (15)	0.0027 (12)	0.0007 (12)	0.0018 (12)
C9'	0.0187 (15)	0.0252 (16)	0.0213 (15)	0.0013 (12)	0.0026 (12)	0.0021 (12)
C10'	0.0199 (14)	0.0213 (15)	0.0160 (14)	0.0035 (12)	0.0017 (11)	−0.0009 (11)
C11'	0.0174 (14)	0.0209 (15)	0.0149 (13)	0.0030 (11)	0.0007 (11)	0.0009 (11)
C12'	0.0222 (15)	0.0231 (15)	0.0154 (14)	0.0000 (12)	0.0004 (11)	0.0026 (11)
C13'	0.0323 (18)	0.0367 (19)	0.0263 (17)	0.0035 (15)	0.0017 (14)	0.0043 (14)
C14'	0.0202 (15)	0.044 (2)	0.0161 (15)	−0.0059 (14)	−0.0006 (12)	−0.0018 (13)
C15'	0.035 (2)	0.0290 (18)	0.047 (2)	0.0034 (15)	−0.0019 (16)	0.0073 (16)
C16'	0.041 (2)	0.043 (2)	0.043 (2)	−0.0023 (17)	−0.0005 (17)	0.0170 (18)
C17'	0.0293 (18)	0.058 (2)	0.0209 (17)	−0.0085 (17)	−0.0013 (14)	0.0122 (16)
C18'	0.035 (2)	0.0308 (19)	0.045 (2)	−0.0044 (15)	0.0185 (17)	−0.0152 (16)
C19'	0.0246 (17)	0.045 (2)	0.050 (2)	0.0079 (15)	0.0074 (16)	0.0244 (18)

O—C13	1.431 (4)	O'—C13'	1.417 (4)
O—N	1.480 (3)	O'—N'	1.474 (3)
N—C8	1.466 (4)	N'—C8'	1.469 (4)
N—C7	1.493 (4)	N'—C7'	1.503 (3)
C1—C2	1.533 (4)	C1'—C2'	1.546 (4)
C1—C6	1.545 (4)	C1'—C6'	1.547 (4)
C1—C11	1.554 (4)	C1'—C7'	1.551 (4)
C1—C7	1.561 (4)	C1'—C11'	1.561 (4)
C2—C3	1.529 (4)	C2'—C3'	1.533 (4)
C2—H2A	0.970	C2'—H2'A	0.970
C2—H2B	0.970	C2'—H2'B	0.970
C3—C4	1.529 (5)	C3'—C4'	1.532 (4)
C3—H3A	0.970	C3'—H3'A	0.970
C3—H3B	0.970	C3'—H3'B	0.970
C4—C5	1.529 (5)	C4'—C5'	1.530 (4)
C4—H4A	0.970	C4'—H4'A	0.970
C4—H4B	0.970	C4'—H4'B	0.970
C5—C6	1.537 (4)	C5'—C6'	1.538 (4)
C5—H5A	0.970	C5'—H5'A	0.970
C5—H5B	0.970	C5'—H5'B	0.970
C6—H6A	0.970	C6'—H6'A	0.970
C6—H6B	0.970	C6'—H6'B	0.970
C7—C12	1.547 (4)	C7'—C12'	1.547 (4)
C7—H7A	0.980	C7'—H7'A	0.980
C8—C9	1.525 (4)	C8'—C9'	1.533 (4)
C8—H8A	0.970	C8'—H8'A	0.970
C8—H8B	0.970	C8'—H8'B	0.970
C9—C10	1.519 (4)	C9'—C10'	1.535 (4)
C9—H9A	0.970	C9'—H9'A	0.970
C9—H9B	0.970	C9'—H9'B	0.970
C10—C11	1.536 (4)	C10'—C11'	1.542 (4)
C10—H10A	0.970	C10'—H10C	0.970
C10—H10B	0.970	C10'—H10D	0.970
C11—H11A	0.970	C11'—H11C	0.970
C11—H11B	0.970	C11'—H11D	0.970
C12—C13	1.527 (4)	C12'—C13'	1.539 (4)
C12—H12A	0.970	C12'—H12C	0.970
C12—H12B	0.970	C12'—H12D	0.970
C13—C14	1.514 (4)	C13'—C14'	1.525 (4)
C13—H13A	0.980	C13'—H13B	0.980
C14—C19	1.390 (4)	C14'—C15'	1.376 (5)
C14—C15	1.393 (4)	C14'—C19'	1.407 (5)
C15—C16	1.385 (4)	C15'—C16'	1.348 (5)
C15—H15A	0.930	C15'—H15B	0.930
C16—C17	1.379 (5)	C16'—C17'	1.348 (5)
C16—H16A	0.930	C16'—H16B	0.930
C17—C18	1.383 (5)	C17'—C18'	1.370 (6)
C17—H17A	0.930	C17'—H17B	0.930
C18—C19	1.392 (5)	C18'—C19'	1.441 (5)
C18—H18A	0.930	C18'—H18B	0.930
C19—H19A	0.930	C19'—H19B	0.930
C13—O—N	103.2 (2)	C13'—O'—N'	104.6 (2)
C8—N—O	103.8 (2)	C8'—N'—O'	103.8 (2)
C8—N—C7	111.2 (2)	C8'—N'—C7'	111.8 (2)
O—N—C7	105.4 (2)	O'—N'—C7'	105.51 (19)
C2—C1—C6	109.4 (2)	C2'—C1'—C6'	109.1 (2)
C2—C1—C11	109.5 (2)	C2'—C1'—C7'	111.1 (2)
C6—C1—C11	110.1 (2)	C6'—C1'—C7'	108.3 (2)
C2—C1—C7	112.5 (2)	C2'—C1'—C11'	108.8 (2)
C6—C1—C7	106.4 (2)	C6'—C1'—C11'	110.1 (2)
C11—C1—C7	108.9 (2)	C7'—C1'—C11'	109.4 (2)
C3—C2—C1	112.9 (3)	C3'—C2'—C1'	112.7 (2)
C3—C2—H2A	109.0	C3'—C2'—H2'A	109.1
C1—C2—H2A	109.0	C1'—C2'—H2'A	109.1
C3—C2—H2B	109.0	C3'—C2'—H2'B	109.1
C1—C2—H2B	109.0	C1'—C2'—H2'B	109.1
H2A—C2—H2B	107.8	H2'A—C2'—H2'B	107.8
C4—C3—C2	111.2 (3)	C4'—C3'—C2'	110.0 (2)
C4—C3—H3A	109.4	C4'—C3'—H3'A	109.7
C2—C3—H3A	109.4	C2'—C3'—H3'A	109.7
C4—C3—H3B	109.4	C4'—C3'—H3'B	109.7
C2—C3—H3B	109.4	C2'—C3'—H3'B	109.7
H3A—C3—H3B	108.0	H3'A—C3'—H3'B	108.2
C3—C4—C5	111.5 (3)	C5'—C4'—C3'	110.9 (2)
C3—C4—H4A	109.3	C5'—C4'—H4'A	109.5
C5—C4—H4A	109.3	C3'—C4'—H4'A	109.5
C3—C4—H4B	109.3	C5'—C4'—H4'B	109.5
C5—C4—H4B	109.3	C3'—C4'—H4'B	109.5
H4A—C4—H4B	108.0	H4'A—C4'—H4'B	108.1
C4—C5—C6	111.4 (3)	C4'—C5'—C6'	112.1 (2)
C4—C5—H5A	109.3	C4'—C5'—H5'A	109.2
C6—C5—H5A	109.3	C6'—C5'—H5'A	109.2
C4—C5—H5B	109.3	C4'—C5'—H5'B	109.2
C6—C5—H5B	109.3	C6'—C5'—H5'B	109.2
H5A—C5—H5B	108.0	H5'A—C5'—H5'B	107.9
C5—C6—C1	112.9 (3)	C5'—C6'—C1'	114.1 (2)
C5—C6—H6A	109.0	C5'—C6'—H6'A	108.7
C1—C6—H6A	109.0	C1'—C6'—H6'A	108.7
C5—C6—H6B	109.0	C5'—C6'—H6'B	108.7
C1—C6—H6B	109.0	C1'—C6'—H6'B	108.7
H6A—C6—H6B	107.8	H6'A—C6'—H6'B	107.6
N—C7—C12	104.7 (2)	N'—C7'—C12'	104.8 (2)
N—C7—C1	110.6 (2)	N'—C7'—C1'	108.3 (2)
C12—C7—C1	117.3 (2)	C12'—C7'—C1'	118.0 (2)
N—C7—H7A	108.0	N'—C7'—H7'A	108.5
C12—C7—H7A	108.0	C12'—C7'—H7'A	108.5
C1—C7—H7A	108.0	C1'—C7'—H7'A	108.5
N—C8—C9	111.0 (2)	N'—C8'—C9'	110.4 (2)
N—C8—H8A	109.4	N'—C8'—H8'A	109.6
C9—C8—H8A	109.4	C9'—C8'—H8'A	109.6
N—C8—H8B	109.4	N'—C8'—H8'B	109.6
C9—C8—H8B	109.4	C9'—C8'—H8'B	109.6
H8A—C8—H8B	108.0	H8'A—C8'—H8'B	108.1
C10—C9—C8	116.2 (3)	C8'—C9'—C10'	115.6 (2)
C10—C9—H9A	108.2	C8'—C9'—H9'A	108.4
C8—C9—H9A	108.2	C10'—C9'—H9'A	108.4
C10—C9—H9B	108.2	C8'—C9'—H9'B	108.4
C8—C9—H9B	108.2	C10'—C9'—H9'B	108.4
H9A—C9—H9B	107.4	H9'A—C9'—H9'B	107.5
C9—C10—C11	114.3 (2)	C9'—C10'—C11'	113.3 (2)
C9—C10—H10A	108.7	C9'—C10'—H10C	108.9
C11—C10—H10A	108.7	C11'—C10'—H10C	108.9
C9—C10—H10B	108.7	C9'—C10'—H10D	108.9
C11—C10—H10B	108.7	C11'—C10'—H10D	108.9
H10A—C10—H10B	107.6	H10C—C10'—H10D	107.7
C10—C11—C1	117.6 (2)	C10'—C11'—C1'	116.6 (2)
C10—C11—H11A	107.9	C10'—C11'—H11C	108.1
C1—C11—H11A	107.9	C1'—C11'—H11C	108.1
C10—C11—H11B	107.9	C10'—C11'—H11D	108.1
C1—C11—H11B	107.9	C1'—C11'—H11D	108.1
H11A—C11—H11B	107.2	H11C—C11'—H11D	107.3
C13—C12—C7	102.9 (2)	C13'—C12'—C7'	102.6 (2)
C13—C12—H12A	111.2	C13'—C12'—H12C	111.3
C7—C12—H12A	111.2	C7'—C12'—H12C	111.3
C13—C12—H12B	111.2	C13'—C12'—H12D	111.3
C7—C12—H12B	111.2	C7'—C12'—H12D	111.3
H12A—C12—H12B	109.1	H12C—C12'—H12D	109.2
O—C13—C14	109.4 (2)	O'—C13'—C14'	107.4 (3)
O—C13—C12	103.1 (2)	O'—C13'—C12'	103.4 (3)
C14—C13—C12	114.1 (3)	C14'—C13'—C12'	116.3 (3)
O—C13—H13A	110.0	O'—C13'—H13B	109.8
C14—C13—H13A	110.0	C14'—C13'—H13B	109.8
C12—C13—H13A	110.0	C12'—C13'—H13B	109.8
C19—C14—C15	119.2 (3)	C15'—C14'—C19'	119.1 (3)
C19—C14—C13	121.9 (3)	C15'—C14'—C13'	123.3 (3)
C15—C14—C13	118.8 (3)	C19'—C14'—C13'	117.4 (3)
C16—C15—C14	120.4 (3)	C16'—C15'—C14'	122.0 (4)
C16—C15—H15A	119.8	C16'—C15'—H15B	119.0
C14—C15—H15A	119.8	C14'—C15'—H15B	119.0
C17—C16—C15	120.1 (3)	C17'—C16'—C15'	120.2 (4)
C17—C16—H16A	119.9	C17'—C16'—H16B	119.9
C15—C16—H16A	119.9	C15'—C16'—H16B	119.9
C16—C17—C18	120.0 (3)	C16'—C17'—C18'	122.1 (3)
C16—C17—H17A	120.0	C16'—C17'—H17B	118.9
C18—C17—H17A	120.0	C18'—C17'—H17B	118.9
C17—C18—C19	120.2 (3)	C17'—C18'—C19'	118.6 (3)
C17—C18—H18A	119.9	C17'—C18'—H18B	120.7
C19—C18—H18A	119.9	C19'—C18'—H18B	120.7
C14—C19—C18	120.0 (3)	C14'—C19'—C18'	117.9 (3)
C14—C19—H19A	120.0	C14'—C19'—H19B	121.0
C18—C19—H19A	120.0	C18'—C19'—H19B	121.0