Ethyl (1R,1'S,2'S,7a'R)-2-oxo-1'-[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetra-methyl-tetra-hydro-3aH-bis-[1,3]dioxolo[4,5-b:4',5'-d]pyran-5-yl]-1',2',5',6',7',7a'-hexa-hydro-2H-spiro-[acenaphthyl-ene-1,3'-pyrrolizine]-2'-carboxyl-ate.

In the title compound, C(32)H(37)NO(8), the central pyran ring adopts a twist-boat conformation and the 1,3-dioxoane rings adopt envelope conformations. The acenaphthyl-enone unit and two C atoms of a pyrrolidine ring are disordered over two sets of sites [occupancy ratio 0.669 (7):0.331 (7)]. The major fraction of the disordered pyrrolidine ring exhibits an envelope conformation while the minor component is essentially planar [maximum deviation = 0.037 (12) Å]. The other pyrrolidine ring also adopts an envelope conformation. The dihedral angle between the mean planes of the two wings of the pyrrolidine ring is 30.6 (2)°. Both the major and minor components of the acenaphthyl-enone unit are essentially planar, the maximum deviations being 0.025 (10) and 0.047 (19) Å, respectively; the dihedral angle between the mean planes of the two components is 1.72 (3)°. The crystal packing features C-H⋯O inter-actions.

Related literature

For applications of spiro­heterocycles, see: Ferguson et al. (2005 ▶). For a related structure, see: Athimoolam et al. (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶)

Experimental

Crystal data

C32H37NO8

M = 563.63

Monoclinic,

a = 11.4723 (4) Å

b = 8.9548 (2) Å

c = 15.0543 (5) Å

β = 96.990 (2)°

V = 1535.07 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.966, T max = 0.974

20295 measured reflections

5063 independent reflections

3469 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.124

S = 1.05

5039 reflections

413 parameters

50 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055760/pv2491sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055760/pv2491Isup2.hkl

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

C32H37NO8	F(000) = 600
Mr = 563.63	Dx = 1.219 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5063 reflections
a = 11.4723 (4) Å	θ = 1.4–30.7°
b = 8.9548 (2) Å	µ = 0.09 mm−1
c = 15.0543 (5) Å	T = 293 K
β = 96.990 (2)°	Block, colourless
V = 1535.07 (8) Å3	0.40 × 0.35 × 0.30 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	5063 independent reflections
Radiation source: fine-focus sealed tube	3469 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 30.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→16
Tmin = 0.966, Tmax = 0.974	k = −12→11
20295 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.0862P] where P = (Fo2 + 2Fc2)/3
5039 reflections	(Δ/σ)max = 0.001
413 parameters	Δρmax = 0.24 e Å−3
50 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11	0.59193 (19)	0.1469 (3)	0.22033 (14)	0.0479 (5)
C1	0.4922 (6)	−0.0874 (7)	0.2582 (4)	0.0537 (15)	0.669 (7)
C2	0.4548 (9)	−0.2257 (11)	0.2815 (5)	0.083 (2)	0.669 (7)
H2	0.5074	−0.3002	0.3027	0.100*	0.669 (7)
C3	0.3315 (7)	−0.2493 (9)	0.2716 (5)	0.094 (2)	0.669 (7)
H3	0.3036	−0.3439	0.2832	0.113*	0.669 (7)
C4	0.2530 (7)	−0.1406 (11)	0.2462 (6)	0.098 (3)	0.669 (7)
H4	0.1731	−0.1620	0.2419	0.118*	0.669 (7)
C7	0.2673 (9)	0.2617 (13)	0.1818 (8)	0.092 (3)	0.669 (7)
H7	0.2190	0.3431	0.1656	0.111*	0.669 (7)
C5	0.2891 (6)	0.0050 (9)	0.2258 (4)	0.0734 (18)	0.669 (7)
C6	0.2182 (7)	0.1330 (12)	0.1992 (5)	0.085 (2)	0.669 (7)
H6	0.1368	0.1254	0.1943	0.102*	0.669 (7)
C8	0.3907 (15)	0.2805 (14)	0.1867 (10)	0.070 (2)	0.669 (7)
H8	0.4221	0.3728	0.1742	0.084*	0.669 (7)
C9	0.4635 (11)	0.1611 (11)	0.2100 (9)	0.0506 (18)	0.669 (7)
C10	0.4099 (7)	0.0250 (9)	0.2313 (5)	0.0528 (17)	0.669 (7)
C12	0.6119 (8)	−0.0220 (12)	0.2612 (8)	0.0480 (16)	0.669 (7)
O1	0.7037 (5)	−0.0726 (7)	0.2904 (4)	0.0670 (11)	0.669 (7)
C11'	0.59193 (19)	0.1469 (3)	0.22033 (14)	0.0479 (5)	0.00
C1'	0.4559 (16)	−0.0469 (19)	0.2460 (11)	0.0537 (15)	0.331 (7)
C2'	0.414 (2)	−0.193 (2)	0.2611 (12)	0.083 (2)	0.331 (7)
H2'	0.4620	−0.2746	0.2782	0.100*	0.331 (7)
C3'	0.285 (2)	−0.198 (3)	0.2462 (15)	0.094 (2)	0.331 (7)
H3'	0.2480	−0.2906	0.2471	0.113*	0.331 (7)
C4'	0.2176 (17)	−0.072 (2)	0.2311 (13)	0.098 (3)	0.331 (7)
H4'	0.1376	−0.0794	0.2351	0.118*	0.331 (7)
C5'	0.2616 (17)	0.063 (2)	0.2105 (11)	0.0734 (18)	0.331 (7)
C7'	0.268 (2)	0.324 (3)	0.1690 (19)	0.092 (3)	0.331 (7)
H7'	0.2281	0.4118	0.1522	0.111*	0.331 (7)
C6'	0.2076 (15)	0.207 (2)	0.1856 (11)	0.085 (2)	0.331 (7)
H6'	0.1263	0.2147	0.1814	0.102*	0.331 (7)
C8'	0.392 (3)	0.323 (4)	0.176 (2)	0.070 (2)	0.331 (7)
H8'	0.4331	0.4074	0.1612	0.084*	0.331 (7)
C9'	0.449 (3)	0.198 (3)	0.203 (2)	0.0506 (18)	0.331 (7)
C10'	0.3912 (17)	0.070 (2)	0.2172 (12)	0.0528 (17)	0.331 (7)
C12'	0.583 (2)	0.000 (3)	0.2520 (18)	0.0480 (16)	0.331 (7)
O1'	0.6700 (14)	−0.0789 (19)	0.2720 (11)	0.0670 (11)	0.331 (7)
C13	0.5891 (3)	0.1171 (5)	0.05317 (18)	0.0780 (9)
H13A	0.5054	0.1335	0.0526	0.094*	0.669 (7)
H13B	0.6022	0.0135	0.0383	0.094*	0.669 (7)
C14	0.6416 (7)	0.2255 (11)	−0.0147 (4)	0.0864 (19)	0.669 (7)
H14A	0.7167	0.1905	−0.0299	0.104*	0.669 (7)
H14B	0.5879	0.2398	−0.0690	0.104*	0.669 (7)
C15	0.6546 (16)	0.368 (3)	0.0428 (13)	0.083 (3)	0.669 (7)
H15A	0.5791	0.4131	0.0490	0.100*	0.669 (7)
H15B	0.7049	0.4412	0.0189	0.100*	0.669 (7)
C13'	0.5891 (3)	0.1171 (5)	0.05317 (18)	0.0780 (9)	0.00
H13C	0.6234	0.0300	0.0283	0.094*	0.331 (7)
H13D	0.5071	0.0968	0.0583	0.094*	0.331 (7)
C14'	0.5997 (15)	0.238 (3)	0.0017 (10)	0.0864 (19)	0.331 (7)
H14C	0.5227	0.2809	−0.0153	0.104*	0.331 (7)
H14D	0.6308	0.2072	−0.0526	0.104*	0.331 (7)
C15'	0.682 (4)	0.358 (7)	0.050 (3)	0.083 (3)	0.331 (7)
H15C	0.7497	0.3742	0.0190	0.100*	0.331 (7)
H15D	0.6402	0.4518	0.0536	0.100*	0.331 (7)
C16	0.7142 (2)	0.2993 (3)	0.13480 (14)	0.0503 (5)
H16	0.7981	0.2820	0.1320	0.060*
C17	0.69672 (17)	0.3832 (3)	0.22092 (13)	0.0416 (4)
H17	0.6296	0.4508	0.2080	0.050*
C18	0.66266 (18)	0.2589 (2)	0.28307 (14)	0.0406 (4)
H18	0.7348	0.2094	0.3095	0.049*
C19	0.5980 (2)	0.3121 (3)	0.35780 (15)	0.0491 (5)
C20	0.5076 (4)	0.2307 (5)	0.4838 (2)	0.0924 (11)
H20A	0.5346	0.3249	0.5106	0.111*
H20B	0.5229	0.1533	0.5288	0.111*
C21	0.3815 (4)	0.2393 (9)	0.4553 (4)	0.146 (2)
H21A	0.3411	0.2600	0.5061	0.220*
H21B	0.3545	0.1458	0.4291	0.220*
H21C	0.3660	0.3176	0.4119	0.220*
C22	0.80032 (17)	0.4724 (2)	0.26659 (14)	0.0411 (4)
H22	0.7875	0.4879	0.3291	0.049*
C23	0.99820 (19)	0.4371 (3)	0.32680 (16)	0.0505 (5)
H23	1.0723	0.4010	0.3085	0.061*
C24	1.0038 (2)	0.6074 (3)	0.33687 (15)	0.0532 (6)
H24	1.0859	0.6402	0.3423	0.064*
C25	0.9321 (2)	0.6970 (3)	0.26499 (14)	0.0538 (6)
H25	0.9173	0.7972	0.2872	0.065*
C26	0.8158 (2)	0.6236 (3)	0.22544 (14)	0.0489 (5)
H26	0.7493	0.6886	0.2338	0.059*
C27	0.9899 (2)	0.5074 (3)	0.47405 (14)	0.0560 (6)
C28	0.8969 (3)	0.4856 (4)	0.5344 (2)	0.0803 (9)
H28A	0.9167	0.4013	0.5727	0.120*
H28B	0.8228	0.4682	0.4990	0.120*
H28C	0.8917	0.5734	0.5703	0.120*
C29	1.1111 (3)	0.5247 (5)	0.5240 (2)	0.0831 (9)
H29A	1.1300	0.4381	0.5606	0.125*
H29B	1.1134	0.6119	0.5613	0.125*
H29C	1.1672	0.5350	0.4820	0.125*
C30	0.9167 (3)	0.7058 (4)	0.11239 (17)	0.0687 (7)
C31	0.9768 (4)	0.6396 (7)	0.0394 (2)	0.1171 (16)
H31A	1.0370	0.7063	0.0247	0.176*
H31B	0.9206	0.6239	−0.0125	0.176*
H31C	1.0114	0.5457	0.0590	0.176*
C32	0.8670 (4)	0.8595 (4)	0.0899 (3)	0.1013 (12)
H32A	0.9286	0.9243	0.0755	0.152*
H32B	0.8335	0.8989	0.1404	0.152*
H32C	0.8074	0.8527	0.0394	0.152*
O2	0.5742 (2)	0.4391 (2)	0.37177 (15)	0.0771 (6)
O3	0.57205 (18)	0.1979 (2)	0.40881 (11)	0.0679 (5)
O4	0.90450 (12)	0.38520 (18)	0.26594 (10)	0.0474 (3)
O5	0.98714 (16)	0.3842 (2)	0.41297 (11)	0.0607 (4)
O6	0.95792 (15)	0.63306 (19)	0.41854 (10)	0.0552 (4)
O7	0.82740 (17)	0.6087 (2)	0.13311 (10)	0.0651 (5)
O8	0.99739 (17)	0.7064 (3)	0.19099 (12)	0.0802 (6)
N1	0.65251 (17)	0.1553 (2)	0.14046 (12)	0.0539 (5)

	U11	U22	U33	U12	U13	U23
C11	0.0449 (11)	0.0493 (13)	0.0481 (11)	−0.0126 (9)	−0.0001 (9)	−0.0063 (9)
C1	0.070 (4)	0.046 (4)	0.045 (2)	−0.020 (2)	0.006 (2)	−0.005 (2)
C2	0.125 (8)	0.074 (5)	0.050 (4)	−0.044 (4)	0.009 (3)	0.002 (3)
C3	0.115 (5)	0.090 (4)	0.079 (4)	−0.065 (4)	0.020 (3)	0.003 (3)
C4	0.088 (6)	0.117 (7)	0.092 (4)	−0.061 (5)	0.022 (4)	−0.005 (5)
C7	0.0487 (18)	0.144 (9)	0.081 (4)	0.012 (5)	−0.006 (2)	0.017 (5)
C5	0.057 (3)	0.108 (5)	0.054 (3)	−0.028 (3)	0.000 (2)	0.003 (3)
C6	0.047 (2)	0.131 (6)	0.073 (3)	−0.012 (4)	−0.005 (2)	0.008 (4)
C8	0.0505 (15)	0.089 (8)	0.067 (4)	0.001 (6)	−0.007 (3)	0.015 (4)
C9	0.035 (4)	0.064 (6)	0.050 (2)	−0.002 (3)	−0.006 (2)	−0.002 (4)
C10	0.051 (3)	0.067 (6)	0.038 (3)	−0.021 (4)	−0.005 (2)	0.007 (3)
C12	0.054 (6)	0.038 (4)	0.049 (3)	0.000 (3)	−0.003 (3)	−0.005 (2)
O1	0.069 (4)	0.0460 (13)	0.078 (3)	0.000 (2)	−0.021 (2)	−0.0076 (18)
C11'	0.0449 (11)	0.0493 (13)	0.0481 (11)	−0.0126 (9)	−0.0001 (9)	−0.0063 (9)
C1'	0.070 (4)	0.046 (4)	0.045 (2)	−0.020 (2)	0.006 (2)	−0.005 (2)
C2'	0.125 (8)	0.074 (5)	0.050 (4)	−0.044 (4)	0.009 (3)	0.002 (3)
C3'	0.115 (5)	0.090 (4)	0.079 (4)	−0.065 (4)	0.020 (3)	0.003 (3)
C4'	0.088 (6)	0.117 (7)	0.092 (4)	−0.061 (5)	0.022 (4)	−0.005 (5)
C5'	0.057 (3)	0.108 (5)	0.054 (3)	−0.028 (3)	0.000 (2)	0.003 (3)
C7'	0.0487 (18)	0.144 (9)	0.081 (4)	0.012 (5)	−0.006 (2)	0.017 (5)
C6'	0.047 (2)	0.131 (6)	0.073 (3)	−0.012 (4)	−0.005 (2)	0.008 (4)
C8'	0.0505 (15)	0.089 (8)	0.067 (4)	0.001 (6)	−0.007 (3)	0.015 (4)
C9'	0.035 (4)	0.064 (6)	0.050 (2)	−0.002 (3)	−0.006 (2)	−0.002 (4)
C10'	0.051 (3)	0.067 (6)	0.038 (3)	−0.021 (4)	−0.005 (2)	0.007 (3)
C12'	0.054 (6)	0.038 (4)	0.049 (3)	0.000 (3)	−0.003 (3)	−0.005 (2)
O1'	0.069 (4)	0.0460 (13)	0.078 (3)	0.000 (2)	−0.021 (2)	−0.0076 (18)
C13	0.085 (2)	0.095 (2)	0.0534 (14)	−0.0276 (18)	0.0040 (13)	−0.0244 (15)
C14	0.092 (5)	0.131 (4)	0.036 (3)	−0.038 (5)	0.007 (2)	−0.009 (3)
C15	0.110 (8)	0.087 (5)	0.044 (4)	−0.026 (7)	−0.027 (5)	0.012 (3)
C13'	0.085 (2)	0.095 (2)	0.0534 (14)	−0.0276 (18)	0.0040 (13)	−0.0244 (15)
C14'	0.092 (5)	0.131 (4)	0.036 (3)	−0.038 (5)	0.007 (2)	−0.009 (3)
C15'	0.110 (8)	0.087 (5)	0.044 (4)	−0.026 (7)	−0.027 (5)	0.012 (3)
C16	0.0503 (12)	0.0582 (14)	0.0416 (11)	−0.0148 (11)	0.0014 (9)	−0.0044 (10)
C17	0.0389 (10)	0.0408 (10)	0.0438 (10)	−0.0055 (8)	0.0006 (8)	0.0021 (8)
C18	0.0383 (10)	0.0382 (10)	0.0444 (10)	−0.0076 (8)	0.0018 (8)	−0.0025 (8)
C19	0.0505 (12)	0.0476 (13)	0.0490 (11)	−0.0121 (10)	0.0060 (9)	−0.0022 (9)
C20	0.128 (3)	0.092 (3)	0.0654 (18)	−0.023 (2)	0.0465 (18)	−0.0008 (17)
C21	0.112 (3)	0.202 (7)	0.141 (4)	−0.018 (4)	0.075 (3)	−0.006 (4)
C22	0.0405 (10)	0.0402 (11)	0.0427 (10)	−0.0050 (8)	0.0053 (8)	−0.0008 (8)
C23	0.0423 (11)	0.0542 (13)	0.0544 (12)	−0.0048 (10)	0.0034 (9)	−0.0086 (10)
C24	0.0506 (12)	0.0584 (14)	0.0499 (12)	−0.0208 (11)	0.0028 (9)	−0.0062 (10)
C25	0.0671 (14)	0.0473 (12)	0.0481 (11)	−0.0229 (11)	0.0110 (10)	−0.0011 (10)
C26	0.0513 (12)	0.0451 (12)	0.0509 (11)	−0.0065 (10)	0.0082 (9)	0.0022 (9)
C27	0.0690 (15)	0.0509 (13)	0.0453 (11)	0.0007 (11)	−0.0041 (10)	−0.0015 (10)
C28	0.100 (2)	0.081 (2)	0.0606 (15)	0.0148 (18)	0.0147 (15)	0.0169 (15)
C29	0.082 (2)	0.086 (2)	0.0726 (18)	−0.0016 (17)	−0.0245 (15)	−0.0066 (16)
C30	0.0733 (17)	0.0831 (19)	0.0518 (13)	−0.0191 (15)	0.0159 (12)	0.0057 (13)
C31	0.124 (3)	0.166 (5)	0.0657 (18)	0.017 (3)	0.0325 (19)	−0.001 (3)
C32	0.144 (3)	0.080 (2)	0.085 (2)	−0.020 (2)	0.031 (2)	0.0277 (19)
O2	0.0996 (15)	0.0524 (11)	0.0876 (14)	−0.0034 (10)	0.0457 (12)	−0.0075 (10)
O3	0.0907 (13)	0.0615 (11)	0.0554 (9)	−0.0129 (10)	0.0244 (9)	0.0028 (8)
O4	0.0422 (8)	0.0447 (8)	0.0537 (8)	−0.0021 (6)	−0.0013 (6)	−0.0106 (7)
O5	0.0763 (11)	0.0476 (9)	0.0547 (10)	−0.0008 (9)	−0.0065 (8)	−0.0003 (7)
O6	0.0745 (11)	0.0457 (9)	0.0439 (8)	−0.0050 (8)	0.0012 (7)	−0.0021 (7)
O7	0.0823 (12)	0.0679 (11)	0.0429 (8)	−0.0218 (10)	−0.0013 (8)	0.0071 (8)
O8	0.0672 (11)	0.1192 (18)	0.0555 (10)	−0.0378 (12)	0.0127 (8)	0.0105 (11)
N1	0.0560 (11)	0.0599 (12)	0.0452 (9)	−0.0163 (9)	0.0041 (8)	−0.0123 (8)

C11—N1	1.462 (3)	C15'—C16	1.39 (4)
C11—C9	1.468 (12)	C15'—H15C	0.9700
C11—C18	1.540 (3)	C15'—H15D	0.9700
C11—C12	1.638 (10)	C16—N1	1.479 (3)
C1—C2	1.370 (11)	C16—C17	1.533 (3)
C1—C10	1.406 (7)	C16—H16	0.9800
C1—C12	1.490 (14)	C17—C22	1.525 (3)
C2—C3	1.419 (13)	C17—C18	1.535 (3)
C2—H2	0.9300	C17—H17	0.9800
C3—C4	1.350 (11)	C18—C19	1.498 (3)
C3—H3	0.9300	C18—H18	0.9800
C4—C5	1.413 (11)	C19—O2	1.194 (3)
C4—H4	0.9300	C19—O3	1.334 (3)
C7—C6	1.324 (13)	C20—O3	1.453 (3)
C7—C8	1.42 (2)	C20—C21	1.460 (7)
C7—H7	0.9300	C20—H20A	0.9700
C5—C10	1.389 (10)	C20—H20B	0.9700
C5—C6	1.434 (11)	C21—H21A	0.9600
C6—H6	0.9300	C21—H21B	0.9600
C8—C9	1.376 (13)	C21—H21C	0.9600
C8—H8	0.9300	C22—O4	1.429 (3)
C9—C10	1.419 (15)	C22—C26	1.508 (3)
C12—O1	1.181 (8)	C22—H22	0.9800
C1'—C10'	1.329 (17)	C23—O5	1.401 (3)
C1'—C2'	1.42 (3)	C23—O4	1.404 (3)
C1'—C12'	1.51 (3)	C23—C24	1.534 (4)
C2'—C3'	1.47 (3)	C23—H23	0.9800
C2'—H2'	0.9300	C24—O6	1.414 (3)
C3'—C4'	1.38 (3)	C24—C25	1.508 (4)
C3'—H3'	0.9300	C24—H24	0.9800
C4'—C5'	1.36 (2)	C25—O8	1.418 (3)
C4'—H4'	0.9300	C25—C26	1.541 (3)
C5'—C6'	1.45 (2)	C25—H25	0.9800
C5'—C10'	1.48 (3)	C26—O7	1.419 (3)
C7'—C6'	1.30 (3)	C26—H26	0.9800
C7'—C8'	1.42 (5)	C27—O6	1.423 (3)
C7'—H7'	0.9300	C27—O5	1.434 (3)
C6'—H6'	0.9300	C27—C28	1.496 (4)
C8'—C9'	1.33 (3)	C27—C29	1.506 (4)
C8'—H8'	0.9300	C28—H28A	0.9600
C9'—C10'	1.35 (4)	C28—H28B	0.9600
C12'—O1'	1.23 (2)	C28—H28C	0.9600
C13—N1	1.463 (3)	C29—H29A	0.9600
C13—C14	1.582 (8)	C29—H29B	0.9600
C13—H13A	0.9700	C29—H29C	0.9600
C13—H13B	0.9700	C30—O7	1.408 (3)
C14—C15	1.54 (3)	C30—O8	1.411 (3)
C14—H14A	0.9700	C30—C31	1.489 (5)
C14—H14B	0.9700	C30—C32	1.512 (5)
C15—C16	1.592 (16)	C31—H31A	0.9600
C15—H15A	0.9700	C31—H31B	0.9600
C15—H15B	0.9700	C31—H31C	0.9600
C14'—C15'	1.55 (5)	C32—H32A	0.9600
C14'—H14C	0.9700	C32—H32B	0.9600
C14'—H14D	0.9700	C32—H32C	0.9600
N1—C11—C9	118.7 (5)	C15—C16—H16	110.1
N1—C11—C18	101.73 (16)	C22—C17—C16	117.59 (17)
C9—C11—C18	117.1 (5)	C22—C17—C18	110.33 (16)
N1—C11—C12	107.3 (5)	C16—C17—C18	103.26 (18)
C9—C11—C12	102.3 (5)	C22—C17—H17	108.4
C18—C11—C12	109.4 (4)	C16—C17—H17	108.4
C2—C1—C10	120.1 (7)	C18—C17—H17	108.4
C2—C1—C12	131.6 (6)	C19—C18—C17	114.40 (18)
C10—C1—C12	108.2 (6)	C19—C18—C11	113.31 (17)
C1—C2—C3	116.5 (7)	C17—C18—C11	104.64 (16)
C1—C2—H2	121.7	C19—C18—H18	108.1
C3—C2—H2	121.7	C17—C18—H18	108.1
C4—C3—C2	123.0 (6)	C11—C18—H18	108.1
C4—C3—H3	118.5	O2—C19—O3	123.8 (2)
C2—C3—H3	118.5	O2—C19—C18	125.4 (2)
C3—C4—C5	121.5 (6)	O3—C19—C18	110.7 (2)
C3—C4—H4	119.2	O3—C20—C21	111.2 (3)
C5—C4—H4	119.2	O3—C20—H20A	109.4
C6—C7—C8	122.6 (8)	C21—C20—H20A	109.4
C6—C7—H7	118.7	O3—C20—H20B	109.4
C8—C7—H7	118.7	C21—C20—H20B	109.4
C10—C5—C4	115.1 (7)	H20A—C20—H20B	108.0
C10—C5—C6	116.2 (6)	C20—C21—H21A	109.5
C4—C5—C6	128.8 (6)	C20—C21—H21B	109.5
C7—C6—C5	120.7 (7)	H21A—C21—H21B	109.5
C7—C6—H6	119.6	C20—C21—H21C	109.5
C5—C6—H6	119.6	H21A—C21—H21C	109.5
C9—C8—C7	119.5 (10)	H21B—C21—H21C	109.5
C9—C8—H8	120.3	O4—C22—C26	110.34 (16)
C7—C8—H8	120.3	O4—C22—C17	108.49 (17)
C8—C9—C10	117.3 (11)	C26—C22—C17	114.17 (18)
C8—C9—C11	131.6 (11)	O4—C22—H22	107.9
C10—C9—C11	111.0 (5)	C26—C22—H22	107.9
C5—C10—C1	123.7 (7)	C17—C22—H22	107.9
C5—C10—C9	123.7 (6)	O5—C23—O4	110.12 (18)
C1—C10—C9	112.7 (7)	O5—C23—C24	104.60 (19)
O1—C12—C1	129.6 (10)	O4—C23—C24	114.4 (2)
O1—C12—C11	124.9 (10)	O5—C23—H23	109.2
C1—C12—C11	105.4 (4)	O4—C23—H23	109.2
C10'—C1'—C2'	127 (2)	C24—C23—H23	109.2
C10'—C1'—C12'	107.3 (19)	O6—C24—C25	108.0 (2)
C2'—C1'—C12'	126.0 (18)	O6—C24—C23	103.40 (19)
C1'—C2'—C3'	110.9 (17)	C25—C24—C23	116.4 (2)
C1'—C2'—H2'	124.5	O6—C24—H24	109.6
C3'—C2'—H2'	124.5	C25—C24—H24	109.6
C4'—C3'—C2'	122.4 (19)	C23—C24—H24	109.6
C4'—C3'—H3'	118.8	O8—C25—C24	107.5 (2)
C2'—C3'—H3'	118.8	O8—C25—C26	103.71 (17)
C5'—C4'—C3'	123.5 (19)	C24—C25—C26	114.92 (19)
C5'—C4'—H4'	118.2	O8—C25—H25	110.1
C3'—C4'—H4'	118.2	C24—C25—H25	110.1
C4'—C5'—C6'	133.3 (19)	C26—C25—H25	110.1
C4'—C5'—C10'	114.8 (18)	O7—C26—C22	110.37 (19)
C6'—C5'—C10'	111.9 (15)	O7—C26—C25	103.79 (17)
C6'—C7'—C8'	123 (2)	C22—C26—C25	111.34 (19)
C6'—C7'—H7'	118.7	O7—C26—H26	110.4
C8'—C7'—H7'	118.7	C22—C26—H26	110.4
C7'—C6'—C5'	122.8 (17)	C25—C26—H26	110.4
C7'—C6'—H6'	118.6	O6—C27—O5	104.34 (15)
C5'—C6'—H6'	118.6	O6—C27—C28	107.9 (2)
C9'—C8'—C7'	118 (3)	O5—C27—C28	109.1 (2)
C9'—C8'—H8'	120.8	O6—C27—C29	111.6 (2)
C7'—C8'—H8'	120.9	O5—C27—C29	110.3 (2)
C8'—C9'—C10'	122 (3)	C28—C27—C29	113.2 (2)
C1'—C10'—C9'	117 (2)	C27—C28—H28A	109.5
C1'—C10'—C5'	120.3 (18)	C27—C28—H28B	109.5
C9'—C10'—C5'	122.1 (18)	H28A—C28—H28B	109.5
O1'—C12'—C1'	127 (3)	C27—C28—H28C	109.5
N1—C13—C14	104.5 (3)	H28A—C28—H28C	109.5
N1—C13—H13A	110.9	H28B—C28—H28C	109.5
C14—C13—H13A	110.9	C27—C29—H29A	109.5
N1—C13—H13B	110.9	C27—C29—H29B	109.5
C14—C13—H13B	110.9	H29A—C29—H29B	109.5
H13A—C13—H13B	108.9	C27—C29—H29C	109.5
C15—C14—C13	99.4 (10)	H29A—C29—H29C	109.5
C15—C14—H14A	111.9	H29B—C29—H29C	109.5
C13—C14—H14A	111.9	O7—C30—O8	103.7 (2)
C15—C14—H14B	111.9	O7—C30—C31	109.4 (3)
C13—C14—H14B	111.9	O8—C30—C31	107.8 (3)
H14A—C14—H14B	109.6	O7—C30—C32	110.3 (3)
C14—C15—C16	99.8 (14)	O8—C30—C32	112.1 (3)
C14—C15—H15A	111.8	C31—C30—C32	113.1 (3)
C16—C15—H15A	111.8	C30—C31—H31A	109.5
C14—C15—H15B	111.8	C30—C31—H31B	109.5
C16—C15—H15B	111.8	H31A—C31—H31B	109.5
H15A—C15—H15B	109.5	C30—C31—H31C	109.5
C15'—C14'—H14C	109.1	H31A—C31—H31C	109.5
C15'—C14'—H14D	109.1	H31B—C31—H31C	109.5
H14C—C14'—H14D	107.9	C30—C32—H32A	109.5
C16—C15'—C14'	104 (4)	C30—C32—H32B	109.5
C16—C15'—H15C	110.9	H32A—C32—H32B	109.5
C14'—C15'—H15C	110.9	C30—C32—H32C	109.5
C16—C15'—H15D	110.9	H32A—C32—H32C	109.5
C14'—C15'—H15D	110.9	H32B—C32—H32C	109.5
H15C—C15'—H15D	108.9	C19—O3—C20	117.6 (2)
C15'—C16—N1	108 (2)	C23—O4—C22	112.91 (17)
C15'—C16—C17	123 (2)	C23—O5—C27	109.65 (18)
N1—C16—C17	105.42 (17)	C24—O6—C27	106.59 (19)
N1—C16—C15	103.3 (9)	C30—O7—C26	108.47 (18)
C17—C16—C15	117.3 (9)	C30—O8—C25	107.68 (19)
C15'—C16—H16	100.2	C13—N1—C11	119.48 (19)
N1—C16—H16	110.1	C13—N1—C16	110.0 (2)
C17—C16—H16	110.1	C11—N1—C16	111.78 (17)
C10—C1—C2—C3	3.7 (12)	C15—C16—C17—C18	133.1 (10)
C12—C1—C2—C3	178.6 (9)	C22—C17—C18—C19	75.1 (2)
C1—C2—C3—C4	−4.1 (12)	C16—C17—C18—C19	−158.35 (18)
C2—C3—C4—C5	1.2 (13)	C22—C17—C18—C11	−160.27 (17)
C3—C4—C5—C10	1.9 (12)	C16—C17—C18—C11	−33.8 (2)
C3—C4—C5—C6	−179.0 (7)	N1—C11—C18—C19	160.73 (19)
C8—C7—C6—C5	1.0 (17)	C9—C11—C18—C19	29.7 (6)
C10—C5—C6—C7	−0.2 (12)	C12—C11—C18—C19	−86.0 (5)
C4—C5—C6—C7	−179.3 (9)	N1—C11—C18—C17	35.5 (2)
C6—C7—C8—C9	0(2)	C9—C11—C18—C17	−95.6 (5)
C7—C8—C9—C10	−2(2)	C12—C11—C18—C17	148.7 (4)
C7—C8—C9—C11	179.9 (12)	C17—C18—C19—O2	−1.1 (3)
N1—C11—C9—C8	−69.0 (17)	C11—C18—C19—O2	−120.9 (3)
C18—C11—C9—C8	53.7 (17)	C17—C18—C19—O3	−179.77 (18)
C12—C11—C9—C8	173.2 (16)	C11—C18—C19—O3	60.4 (2)
N1—C11—C9—C10	113.0 (8)	C16—C17—C22—O4	−42.8 (2)
C18—C11—C9—C10	−124.3 (8)	C18—C17—C22—O4	75.2 (2)
C12—C11—C9—C10	−4.7 (11)	C16—C17—C22—C26	80.7 (2)
C4—C5—C10—C1	−2.3 (11)	C18—C17—C22—C26	−161.32 (17)
C6—C5—C10—C1	178.5 (7)	O5—C23—C24—O6	−18.3 (2)
C4—C5—C10—C9	177.4 (10)	O4—C23—C24—O6	102.3 (2)
C6—C5—C10—C9	−1.8 (13)	O5—C23—C24—C25	−136.6 (2)
C2—C1—C10—C5	−0.6 (12)	O4—C23—C24—C25	−16.0 (3)
C12—C1—C10—C5	−176.6 (8)	O6—C24—C25—O8	163.24 (19)
C2—C1—C10—C9	179.7 (9)	C23—C24—C25—O8	−81.0 (2)
C12—C1—C10—C9	3.7 (11)	O6—C24—C25—C26	−81.9 (2)
C8—C9—C10—C5	3.0 (18)	C23—C24—C25—C26	33.9 (3)
C11—C9—C10—C5	−178.7 (7)	O4—C22—C26—O7	66.0 (2)
C8—C9—C10—C1	−177.2 (12)	C17—C22—C26—O7	−56.5 (2)
C11—C9—C10—C1	1.1 (13)	O4—C22—C26—C25	−48.7 (2)
C2—C1—C12—O1	−5.6 (19)	C17—C22—C26—C25	−171.18 (18)
C10—C1—C12—O1	169.8 (12)	O8—C25—C26—O7	−3.2 (3)
C2—C1—C12—C11	178.3 (8)	C24—C25—C26—O7	−120.3 (2)
C10—C1—C12—C11	−6.3 (9)	O8—C25—C26—C22	115.5 (2)
N1—C11—C12—O1	64.7 (12)	C24—C25—C26—C22	−1.6 (3)
C9—C11—C12—O1	−169.7 (12)	O2—C19—O3—C20	2.1 (4)
C18—C11—C12—O1	−44.9 (13)	C18—C19—O3—C20	−179.1 (3)
N1—C11—C12—C1	−119.0 (6)	C21—C20—O3—C19	83.4 (4)
C9—C11—C12—C1	6.6 (9)	O5—C23—O4—C22	81.7 (2)
C18—C11—C12—C1	131.5 (6)	C24—C23—O4—C22	−35.8 (3)
C10'—C1'—C2'—C3'	−4(3)	C26—C22—O4—C23	70.9 (2)
C12'—C1'—C2'—C3'	−178 (2)	C17—C22—O4—C23	−163.39 (17)
C1'—C2'—C3'—C4'	−8(3)	O4—C23—O5—C27	−125.5 (2)
C2'—C3'—C4'—C5'	14 (3)	C24—C23—O5—C27	−2.1 (2)
C3'—C4'—C5'—C6'	175 (2)	O6—C27—O5—C23	21.6 (2)
C3'—C4'—C5'—C10'	−8(3)	C28—C27—O5—C23	136.7 (2)
C8'—C7'—C6'—C5'	−1(4)	C29—C27—O5—C23	−98.4 (3)
C4'—C5'—C6'—C7'	180 (2)	C25—C24—O6—C27	156.06 (18)
C10'—C5'—C6'—C7'	2(3)	C23—C24—O6—C27	32.1 (2)
C6'—C7'—C8'—C9'	−3(5)	O5—C27—O6—C24	−33.8 (2)
C7'—C8'—C9'—C10'	6(5)	C28—C27—O6—C24	−149.8 (2)
C2'—C1'—C10'—C9'	−177 (2)	C29—C27—O6—C24	85.3 (2)
C12'—C1'—C10'—C9'	−2(3)	O8—C30—O7—C26	33.6 (3)
C2'—C1'—C10'—C5'	9(3)	C31—C30—O7—C26	148.4 (3)
C12'—C1'—C10'—C5'	−175.6 (18)	C32—C30—O7—C26	−86.6 (3)
C8'—C9'—C10'—C1'	−179 (3)	C22—C26—O7—C30	−138.0 (2)
C8'—C9'—C10'—C5'	−5(4)	C25—C26—O7—C30	−18.6 (3)
C4'—C5'—C10'—C1'	−3(3)	O7—C30—O8—C25	−35.8 (3)
C6'—C5'—C10'—C1'	174.8 (19)	C31—C30—O8—C25	−151.7 (3)
C4'—C5'—C10'—C9'	−177 (2)	C32—C30—O8—C25	83.2 (3)
C6'—C5'—C10'—C9'	1(3)	C24—C25—O8—C30	146.0 (2)
C10'—C1'—C12'—O1'	−176 (3)	C26—C25—O8—C30	23.9 (3)
C2'—C1'—C12'—O1'	−1(4)	C14—C13—N1—C11	145.8 (4)
N1—C13—C14—C15	−38.9 (8)	C14—C13—N1—C16	14.6 (5)
C13—C14—C15—C16	46.4 (11)	C9—C11—N1—C13	−24.6 (6)
C14'—C15'—C16—N1	−2(3)	C18—C11—N1—C13	−154.7 (3)
C14'—C15'—C16—C17	−125 (2)	C12—C11—N1—C13	90.5 (5)
C14'—C15'—C16—C15	−67 (18)	C9—C11—N1—C16	105.8 (5)
C14—C15—C16—C15'	79 (19)	C18—C11—N1—C16	−24.3 (2)
C14—C15—C16—N1	−39.1 (12)	C12—C11—N1—C16	−139.1 (4)
C14—C15—C16—C17	−154.6 (7)	C15'—C16—N1—C13	6(2)
C15'—C16—C17—C22	−96 (2)	C17—C16—N1—C13	138.8 (2)
N1—C16—C17—C22	140.62 (19)	C15—C16—N1—C13	15.1 (9)
C15—C16—C17—C22	−105.1 (10)	C15'—C16—N1—C11	−129 (2)
C15'—C16—C17—C18	143 (2)	C17—C16—N1—C11	3.6 (2)
N1—C16—C17—C18	18.9 (2)	C15—C16—N1—C11	−120.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O8i	0.93	2.37	3.252 (9)	157
C26—H26···O1ii	0.98	2.38	3.211 (7)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O8i	0.93	2.37	3.252 (9)	157
C26—H26⋯O1ii	0.98	2.38	3.211 (7)	143

Symmetry codes: (i) ; (ii) .