Ethyl (1R,1′S,2′S,7a'R)-2-oxo-1′-[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetra­methyl­tetra­hydro-3aH-bis­[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl]-1′,2′,5′,6′,7′,7a'-hexa­hydro-2H-spiro­[acenaphthyl­ene-1,3′-pyrrolizine]-2′-carboxyl­ate

Jagadeesan, G.; Sethusankar, K.; Prasanna, R.; Raghunathan, R.

doi:10.1107/S1600536811055760

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o382-o383

doi:10.1107/S1600536811055760

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Ethyl (1R,1′S,2′S,7a'R)-2-oxo-1′-[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl]-1′,2′,5′,6′,7′,7a'-hexahydro-2H-spiro[acenaphthylene-1,3′-pyrrolizine]-2′-carboxylate

G. Jagadeesan,^a K. Sethusankar,^b ^* R. Prasanna ^c and R. Raghunathan ^c

^aDepartment of Physics, Dr MGR Educational and Research Institute, Dr MGR University, Chennai 600 095, India, ^bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 28 November 2011; accepted 26 December 2011; online 14 January 2012)

In the title compound, C₃₂H₃₇NO₈, the central pyran ring adopts a twist-boat conformation and the 1,3-dioxoane rings adopt envelope conformations. The acenaphthylenone 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 acenaphthylenone 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 interactions.

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_r = 563.63
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.124
S = 1.05
5039 reflections
413 parameters
50 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.15 e Å⁻³

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) x-1, y-1, z; (ii) x, y+1, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055760/pv2491sup1.cif

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

checkCIF report

Comment top

The design and novel synthesis of glycospiroheterocycles are interesting because of the synthetic challenges they present and their biological profile against viruses, bacteria, and cancer cells (Ferguson et al., 2005). We have synthesized a novel glycospiroheterocyclic compound and determined its crystal structure which is presented in this article.

The tittle compound (Fig. 1) exhibits structural similarities with an already reported crystal structure of a closely related compound (Athimoolam et al., 2008). The central pyran ring (C22–C26/O4) in the title compound adopts a twist-boat conformation with puckering parameters (Cremer & Pople, 1975): Q = 0.617 (2) Å, θ = 103.87 (19)° and ϕ = 220.2 (2)°. The 1,3–dioxoane rings, (C23/C24/O5/O6/C27) and (C25/C26/O7/O8/C30), adopt envelope conformations with O6 and C30 atoms 0.195 (2) and -0.200 (3) Å, respectively, out of the planes formed by the remaining atoms of the rings.

The acenaphthylenone moiety (C1–C12/O1) and C13 and C14 atoms of a pyrrolidine ring were disordered over two positions with site occupancy factors 0.670 (7):0.330 (7), representing major and minor components, respectively. The major fraction of the pyrrolidine ring N1/C13–C16 exhibits a C14-envelope conformation with C14 0.289 (9) Å out of the mean plane of the rest of the ring atoms while the minor component is essentially planar with maximum deviation of any atom from the mean plane formed by the rings atoms being 0.037 (12) Å for C13-atom. The pyrrolidine ring (N1/C11/C16—C18) adopts a C18-envelope conformation with C18 deviating from the mean plane of the remaining ring atoms by 0.225 (2) Å. The "butter-fly angle" between the mean planes N1/C11/C17/C18 and N1/C13/C15/C16 is 30.6 (2) °, in the pyrrolidine ring.

The major and minor components of the acenaphthylenone moiety (C1–C12/O1) are essentially planar with maximum deviations of atoms C2 and C1', 0.025 (10) Å and 0.047 (19) Å, respectively, and the dihedral angle between the mean planes of the two components is 1.72 (3)°. The crystal packing is stabilized by C—H···O hydrogen bonds via C4—H4···O8 and C26—H26···O1 intermolecular interactions (Tab. 1 and Fig. 2).

Related literature top

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 top

A mixture of 6,7-dideoxy-1,2:3,4-diisopropylidene-D-galacto-Oct- 6-enoethylpyranuronate (1 eq.), acenaphthenequinone (1 eq.) and L-proline (1.2 eq.) was refluxed at 413 K in toluene for about 6 hrs under Dean stark reaction condition to give 1,2:3,4-diisopropylidene-5-C[[2^'.3^''] spirooxindolo-3^'-ethoxycarbonylpyrrolizidine]-D-galactopyranose. After the completion of reaction as indicated by TLC, solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using hexane: EtOAc (4:1) as eluent. Block-shaped single crystals of the title compound suitable for X-ray diffraction analysis were obtained from a solution of hexane/ethyl acetate (4:1) by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme, displacement ellipsoids are drawn at 30% probability level. H atoms are present as small spheres of arbitary radius. The minor fractions of the disordered acenapthenequinone and pyrrolidine groups have been represented by broken bonds.
	Fig. 2. The packing arrangement of the tittle compound in the unit cell; The Dashed lines indicate the C–H···O interactions. H-atoms not involved in hydrogen bonds have been excluded for clarity.

Ethyl (1R,1'S,2'S,7a'R)-2-oxo- 1'-[(3aR,5R,5aS,8aS,8bR)-2,2,7,7- tetramethyltetrahydro-3aH- bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-5-yl]-1',2',5',6',7',7a'- hexahydro-2H-spiro[acenaphthylene-1,3'-pyrrolizine]-2'-carboxylate top

Crystal data top

C₃₂H₃₇NO₈	F(000) = 600
M_r = 563.63	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0616P)² + 0.0862P] where P = (F_o² + 2F_c²)/3
5039 reflections	(Δ/σ)_max = 0.001
413 parameters	Δρ_max = 0.24 e Å⁻³
50 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₃₂H₃₇NO₈	V = 1535.07 (8) Å³
M_r = 563.63	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.4723 (4) Å	µ = 0.09 mm⁻¹
b = 8.9548 (2) Å	T = 293 K
c = 15.0543 (5) Å	0.40 × 0.35 × 0.30 mm
β = 96.990 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5063 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3469 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.974	R_int = 0.026
20295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	50 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
5039 reflections	Δρ_min = −0.15 e Å⁻³
413 parameters

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	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y−1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₃₂H₃₇NO₈
M_r	563.63
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	11.4723 (4), 8.9548 (2), 15.0543 (5)
β (°)	96.990 (2)
V (Å³)	1535.07 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.35 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.966, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	20295, 5063, 3469
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.719

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.124, 1.05
No. of reflections	5039
No. of parameters	413
No. of restraints	50
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.15

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1, y−1, z; (ii) x, y+1, z.

Acknowledgements

GJ and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Department of Physics, for providing facilities in the department to carry out this work.

References

Athimoolam, S., Radha, V. A., Bahadur, S. A., Kumar, R. R. & Perumal, S. (2008). Acta Cryst. E64, o95–o96. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ferguson, N. M., Cummings, D. A. T., Cauchemez, S., Fraser, C., Riley, S., Meeyai, A., Iamsirithaworn, S. & Burke, D. S. (2005). Nature (London), 437, 209–214. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 2| February 2012| Pages o382-o383

doi:10.1107/S1600536811055760

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl (1R,1′S,2′S,7a'R)-2-oxo-1′-[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetra­methyl­tetra­hydro-3aH-bis­­[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl]-1′,2′,5′,6′,7′,7a'-hexa­hydro-2H-spiro­[ace­naphthyl­ene-1,3′-pyrrolizine]-2′-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl (1R,1′S,2′S,7a'R)-2-oxo-1′-[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl]-1′,2′,5′,6′,7′,7a'-hexahydro-2H-spiro[acenaphthylene-1,3′-pyrrolizine]-2′-carboxylate