Eth­yl 2,2′′-dioxo-2′,3′,5′,6′,7′,7a′-hexa­hydro­acenaphthene-1-spiro-3′-1′H-pyrrolizine-2′spiro-1′′-acenaphthene-1-carboxyl­ate

In the title compound, C₃₂H₂₅NO₄, the mean plane through the pyrrolizidine system is almost perpendicular [dihedral angle 88.9 (1)°] to that through one of the acenaphthene units, and the dihedral angle between the pyrrolizidine and the second acenaphthene system is 81.6 (1)°. In the pyrrolizidine system, one of the rings is in a half-chair conformation while the other is in an envelope conformation. The overall conformation is twisted about the fusion bond. The crystal structure is stabilized by a C—H...O inter­molecular hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.061
• wR factor = 0.177
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.92 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.21 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.09
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C32    -   C33     ..       5.50 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C32

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Ethyl 2,2''-dioxo-2,3,5,6,7,7a-hexahydroacenaphthene- 1-spiro-3'-1'H-pyrrolizine-2'spiro-1''-acenaphthene-1-carboxylate

Crystal data

C32H25NO4	F(000) = 1024
Mr = 487.53	Dx = 1.312 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4014 reflections
a = 14.8348 (12) Å	θ = 2.3–26°
b = 11.1902 (9) Å	µ = 0.09 mm^−1
c = 16.0909 (13) Å	T = 293 K
β = 112.479 (1)°	Block, colourless
V = 2468.2 (3) Å^3	0.23 × 0.21 × 0.20 mm
Z = 4

Data collection

CCD Area Detector diffractometer	4065 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 28.0°, θmin = 2.3°
ω scans	h = −19→18
14755 measured reflections	k = −12→14
5507 independent reflections	l = −20→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.178	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.5944P] where P = (Fo^2 + 2Fc^2)/3
5507 reflections	(Δ/σ)max < 0.001
335 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

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	0.30852 (12)	0.67603 (14)	0.16455 (11)	0.0646 (5)
O2	0.41618 (10)	0.90583 (18)	0.27331 (12)	0.0742 (5)
O3	0.14889 (14)	0.86574 (19)	0.38436 (12)	0.0817 (6)
O4	0.28596 (12)	0.95796 (14)	0.39689 (10)	0.0581 (4)
N1	0.11443 (11)	0.80564 (13)	0.11873 (10)	0.0397 (4)
C2	0.20470 (13)	0.85856 (16)	0.12126 (12)	0.0385 (4)
C3	0.23868 (12)	0.92639 (16)	0.21367 (12)	0.0372 (4)
C4	0.21811 (14)	0.83142 (17)	0.27371 (13)	0.0415 (4)
H4	0.2710	0.7725	0.2916	0.050*
C5	0.12430 (14)	0.77073 (16)	0.21053 (13)	0.0409 (4)
H5	0.0690	0.8036	0.2222	0.049*
C6	0.11747 (18)	0.63465 (18)	0.20938 (15)	0.0553 (5)
H6A	0.1809	0.5981	0.2236	0.066*
H6B	0.0898	0.6061	0.2514	0.066*
C7	0.0504 (2)	0.6098 (2)	0.11340 (18)	0.0842 (9)
H7A	0.0625	0.5308	0.0952	0.101*
H7B	−0.0173	0.6146	0.1068	0.101*
C8	0.07283 (17)	0.70443 (18)	0.05737 (15)	0.0549 (5)
H8A	0.1193	0.6747	0.0332	0.066*
H8B	0.0139	0.7286	0.0078	0.066*
C9	0.28774 (14)	0.76746 (18)	0.12179 (13)	0.0461 (5)
C10	0.32969 (14)	0.81393 (19)	0.05870 (13)	0.0466 (5)
C11	0.40537 (16)	0.7751 (2)	0.03628 (16)	0.0599 (6)
H11	0.4427	0.7092	0.0645	0.072*
C12	0.42449 (18)	0.8385 (3)	−0.03075 (18)	0.0712 (7)
H12	0.4760	0.8140	−0.0461	0.085*
C13	0.37009 (18)	0.9345 (3)	−0.07397 (17)	0.0670 (7)
H13	0.3856	0.9739	−0.1177	0.080*
C14	0.29069 (15)	0.9755 (2)	−0.05368 (14)	0.0508 (5)
C15	0.27334 (13)	0.91201 (17)	0.01440 (13)	0.0419 (4)
C16	0.19654 (13)	0.93885 (16)	0.04237 (12)	0.0388 (4)
C17	0.13357 (14)	1.02852 (17)	−0.00035 (13)	0.0451 (5)
H17	0.0806	1.0462	0.0150	0.054*
C18	0.15007 (16)	1.0941 (2)	−0.06823 (14)	0.0539 (5)
H18	0.1074	1.1558	−0.0967	0.065*
C19	0.22586 (17)	1.0706 (2)	−0.09364 (15)	0.0591 (6)
H19	0.2350	1.1173	−0.1375	0.071*
C20	0.34626 (13)	0.9702 (2)	0.24502 (13)	0.0472 (5)
C21	0.34409 (14)	1.1018 (2)	0.23421 (13)	0.0481 (5)
C22	0.41476 (16)	1.1867 (3)	0.24326 (17)	0.0666 (7)
H22	0.4795	1.1650	0.2576	0.080*
C23	0.3854 (2)	1.3073 (3)	0.2300 (2)	0.0770 (8)
H23	0.4322	1.3652	0.2347	0.092*
C24	0.2925 (2)	1.3427 (2)	0.21060 (17)	0.0661 (7)
H24	0.2771	1.4235	0.2027	0.079*
C25	0.21823 (16)	1.25861 (18)	0.20220 (13)	0.0478 (5)
C26	0.24767 (13)	1.13829 (17)	0.21335 (12)	0.0389 (4)
C27	0.18338 (12)	1.04260 (15)	0.20476 (12)	0.0342 (4)
C28	0.08795 (13)	1.06795 (17)	0.18854 (13)	0.0397 (4)
H28	0.0439	1.0068	0.1842	0.048*
C29	0.05728 (14)	1.18864 (18)	0.17844 (14)	0.0465 (5)
H29	−0.0077	1.2056	0.1671	0.056*
C30	0.11928 (16)	1.28065 (18)	0.18464 (15)	0.0514 (5)
H30	0.0961	1.3588	0.1772	0.062*
C31	0.21192 (15)	0.88436 (18)	0.35685 (14)	0.0477 (5)
C32	0.2861 (2)	1.0272 (3)	0.47313 (19)	0.0772 (8)
H32A	0.2975	0.9752	0.5244	0.093*
H32B	0.2235	1.0662	0.4585	0.093*
C33	0.3633 (4)	1.1161 (4)	0.4946 (3)	0.1344 (17)
H33A	0.4254	1.0767	0.5133	0.202*
H33B	0.3617	1.1665	0.5423	0.202*
H33C	0.3537	1.1639	0.4423	0.202*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0814 (11)	0.0583 (9)	0.0648 (11)	0.0335 (8)	0.0400 (9)	0.0198 (8)
O2	0.0419 (8)	0.0983 (13)	0.0777 (12)	0.0219 (8)	0.0175 (8)	0.0036 (10)
O3	0.0963 (13)	0.1081 (15)	0.0632 (12)	−0.0387 (11)	0.0555 (10)	−0.0232 (10)
O4	0.0704 (10)	0.0652 (10)	0.0441 (9)	−0.0110 (7)	0.0280 (7)	−0.0076 (7)
N1	0.0462 (8)	0.0365 (8)	0.0378 (9)	0.0009 (6)	0.0176 (7)	0.0010 (6)
C2	0.0425 (9)	0.0394 (9)	0.0363 (10)	0.0100 (7)	0.0182 (7)	0.0048 (7)
C3	0.0354 (8)	0.0426 (10)	0.0358 (10)	0.0052 (7)	0.0162 (7)	0.0025 (7)
C4	0.0494 (10)	0.0397 (10)	0.0381 (11)	0.0093 (8)	0.0199 (8)	0.0061 (8)
C5	0.0515 (10)	0.0359 (9)	0.0409 (11)	0.0055 (8)	0.0237 (8)	0.0047 (8)
C6	0.0796 (14)	0.0380 (11)	0.0539 (14)	0.0023 (10)	0.0317 (11)	0.0055 (9)
C7	0.123 (2)	0.0436 (13)	0.0652 (17)	−0.0190 (14)	0.0131 (15)	0.0025 (12)
C8	0.0688 (13)	0.0454 (11)	0.0495 (13)	−0.0047 (9)	0.0215 (10)	−0.0055 (9)
C9	0.0518 (10)	0.0500 (11)	0.0393 (11)	0.0146 (9)	0.0206 (8)	0.0021 (9)
C10	0.0472 (10)	0.0572 (12)	0.0378 (11)	0.0069 (9)	0.0189 (8)	−0.0039 (9)
C11	0.0536 (11)	0.0781 (16)	0.0540 (14)	0.0142 (11)	0.0272 (10)	−0.0035 (12)
C12	0.0594 (13)	0.103 (2)	0.0650 (16)	0.0080 (14)	0.0387 (12)	−0.0028 (14)
C13	0.0653 (14)	0.0929 (19)	0.0555 (15)	−0.0062 (13)	0.0372 (12)	0.0038 (13)
C14	0.0535 (11)	0.0632 (13)	0.0389 (12)	−0.0090 (10)	0.0211 (9)	−0.0017 (9)
C15	0.0436 (9)	0.0497 (11)	0.0337 (10)	−0.0021 (8)	0.0161 (8)	−0.0040 (8)
C16	0.0418 (9)	0.0415 (10)	0.0327 (10)	−0.0005 (7)	0.0139 (7)	−0.0005 (7)
C17	0.0455 (10)	0.0473 (11)	0.0419 (11)	0.0033 (8)	0.0158 (8)	0.0052 (8)
C18	0.0589 (12)	0.0526 (12)	0.0448 (12)	0.0025 (9)	0.0137 (10)	0.0123 (9)
C19	0.0682 (14)	0.0665 (14)	0.0444 (13)	−0.0086 (11)	0.0237 (11)	0.0126 (10)
C20	0.0338 (9)	0.0729 (14)	0.0369 (11)	0.0071 (9)	0.0158 (8)	−0.0018 (9)
C21	0.0412 (9)	0.0677 (13)	0.0372 (11)	−0.0110 (9)	0.0170 (8)	−0.0056 (9)
C22	0.0478 (11)	0.102 (2)	0.0569 (15)	−0.0253 (12)	0.0272 (10)	−0.0157 (13)
C23	0.0858 (18)	0.0770 (18)	0.0819 (19)	−0.0450 (15)	0.0474 (15)	−0.0207 (14)
C24	0.0867 (17)	0.0557 (13)	0.0659 (16)	−0.0273 (12)	0.0402 (13)	−0.0108 (11)
C25	0.0683 (13)	0.0420 (10)	0.0376 (11)	−0.0139 (9)	0.0253 (9)	−0.0051 (8)
C26	0.0430 (9)	0.0476 (10)	0.0292 (10)	−0.0072 (7)	0.0174 (7)	−0.0036 (7)
C27	0.0376 (8)	0.0372 (9)	0.0302 (9)	0.0015 (7)	0.0157 (7)	0.0010 (7)
C28	0.0381 (9)	0.0391 (9)	0.0445 (11)	0.0007 (7)	0.0186 (8)	0.0000 (8)
C29	0.0489 (10)	0.0469 (11)	0.0475 (12)	0.0112 (8)	0.0228 (9)	0.0027 (9)
C30	0.0702 (13)	0.0362 (10)	0.0507 (13)	0.0067 (9)	0.0265 (10)	0.0012 (9)
C31	0.0596 (12)	0.0472 (11)	0.0396 (11)	−0.0033 (9)	0.0225 (9)	0.0043 (9)
C32	0.106 (2)	0.0831 (19)	0.0532 (16)	−0.0271 (15)	0.0417 (14)	−0.0226 (13)
C33	0.187 (4)	0.130 (3)	0.106 (3)	−0.072 (3)	0.079 (3)	−0.053 (3)

Geometric parameters (Å, º)

O1—C9	1.205 (2)	C13—H13	0.9300
O2—C20	1.201 (2)	C14—C15	1.409 (3)
O3—C31	1.196 (2)	C14—C19	1.413 (3)
O4—C31	1.326 (2)	C15—C16	1.408 (3)
O4—C32	1.450 (3)	C16—C17	1.364 (3)
N1—C2	1.450 (2)	C17—C18	1.413 (3)
N1—C8	1.474 (3)	C17—H17	0.9300
N1—C5	1.480 (2)	C18—C19	1.361 (3)
C2—C16	1.522 (3)	C18—H18	0.9300
C2—C3	1.571 (3)	C19—H19	0.9300
C2—C9	1.596 (2)	C20—C21	1.481 (3)
C3—C27	1.515 (2)	C21—C22	1.381 (3)
C3—C4	1.543 (3)	C21—C26	1.400 (3)
C3—C20	1.558 (3)	C22—C23	1.409 (4)
C4—C31	1.498 (3)	C22—H22	0.9300
C4—C5	1.533 (3)	C23—C24	1.352 (4)
C4—H4	0.9800	C23—H23	0.9300
C5—C6	1.526 (3)	C24—C25	1.415 (3)
C5—H5	0.9800	C24—H24	0.9300
C6—C7	1.509 (3)	C25—C26	1.406 (3)
C6—H6A	0.9700	C25—C30	1.407 (3)
C6—H6B	0.9700	C26—C27	1.405 (2)
C7—C8	1.508 (3)	C27—C28	1.368 (2)
C7—H7A	0.9700	C28—C29	1.414 (3)
C7—H7B	0.9700	C28—H28	0.9300
C8—H8A	0.9700	C29—C30	1.359 (3)
C8—H8B	0.9700	C29—H29	0.9300
C9—C10	1.473 (3)	C30—H30	0.9300
C10—C11	1.374 (3)	C32—C33	1.456 (5)
C10—C15	1.399 (3)	C32—H32A	0.9700
C11—C12	1.407 (4)	C32—H32B	0.9700
C11—H11	0.9300	C33—H33A	0.9600
C12—C13	1.364 (4)	C33—H33B	0.9600
C12—H12	0.9300	C33—H33C	0.9600
C13—C14	1.414 (3)
C31—O4—C32	118.40 (18)	C10—C15—C16	113.79 (17)
C2—N1—C8	118.6 (2)	C10—C15—C14	122.72 (18)
C2—N1—C5	110.0 (1)	C16—C15—C14	123.47 (18)
C8—N1—C5	108.8 (2)	C17—C16—C15	118.53 (18)
N1—C2—C16	116.08 (14)	C17—C16—C2	132.48 (17)
N1—C2—C3	100.5 (1)	C15—C16—C2	108.95 (15)
C16—C2—C3	113.50 (15)	C16—C17—C18	118.95 (19)
N1—C2—C9	116.21 (15)	C16—C17—H17	120.5
C16—C2—C9	101.33 (14)	C18—C17—H17	120.5
C3—C2—C9	109.62 (14)	C19—C18—C17	122.6 (2)
C27—C3—C4	114.9 (1)	C19—C18—H18	118.7
C27—C3—C20	102.2 (2)	C17—C18—H18	118.7
C4—C3—C20	116.0 (2)	C18—C19—C14	120.4 (2)
C27—C3—C2	111.0 (1)	C18—C19—H19	119.8
C4—C3—C2	101.0 (1)	C14—C19—H19	119.8
C20—C3—C2	112.2 (1)	O2—C20—C21	128.16 (19)
C31—C4—C5	114.68 (16)	O2—C20—C3	124.3 (2)
C31—C4—C3	112.41 (16)	C21—C20—C3	107.55 (15)
C5—C4—C3	103.69 (14)	C22—C21—C26	119.3 (2)
C31—C4—H4	108.6	C22—C21—C20	133.6 (2)
C5—C4—H4	108.6	C26—C21—C20	107.02 (16)
C3—C4—H4	108.6	C21—C22—C23	117.7 (2)
N1—C5—C6	105.70 (15)	C21—C22—H22	121.1
N1—C5—C4	105.26 (14)	C23—C22—H22	121.1
C6—C5—C4	119.30 (17)	C24—C23—C22	123.0 (2)
N1—C5—H5	108.7	C24—C23—H23	118.5
C6—C5—H5	108.7	C22—C23—H23	118.5
C4—C5—H5	108.7	C23—C24—C25	121.0 (2)
C7—C6—C5	102.17 (18)	C23—C24—H24	119.5
C7—C6—H6A	111.3	C25—C24—H24	119.5
C5—C6—H6A	111.3	C26—C25—C30	116.30 (17)
C7—C6—H6B	111.3	C26—C25—C24	115.6 (2)
C5—C6—H6B	111.3	C30—C25—C24	128.1 (2)
H6A—C6—H6B	109.2	C21—C26—C27	113.20 (17)
C8—C7—C6	105.8 (2)	C21—C26—C25	123.34 (18)
C8—C7—H7A	110.6	C27—C26—C25	123.46 (17)
C6—C7—H7A	110.6	C28—C27—C26	118.35 (16)
C8—C7—H7B	110.6	C28—C27—C3	132.83 (16)
C6—C7—H7B	110.6	C26—C27—C3	108.80 (15)
H7A—C7—H7B	108.7	C27—C28—C29	118.96 (17)
N1—C8—C7	105.69 (18)	C27—C28—H28	120.5
N1—C8—H8A	110.6	C29—C28—H28	120.5
C7—C8—H8A	110.6	C30—C29—C28	122.41 (18)
N1—C8—H8B	110.6	C30—C29—H29	118.8
C7—C8—H8B	110.6	C28—C29—H29	118.8
H8A—C8—H8B	108.7	C29—C30—C25	120.48 (18)
O1—C9—C10	127.55 (18)	C29—C30—H30	119.8
O1—C9—C2	124.99 (18)	C25—C30—H30	119.8
C10—C9—C2	107.41 (16)	O3—C31—O4	123.2 (2)
C11—C10—C15	120.2 (2)	O3—C31—C4	125.83 (19)
C11—C10—C9	132.2 (2)	O4—C31—C4	110.94 (17)
C15—C10—C9	107.49 (16)	O4—C32—C33	108.2 (2)
C10—C11—C12	117.8 (2)	O4—C32—H32A	110.1
C10—C11—H11	121.1	C33—C32—H32A	110.1
C12—C11—H11	121.1	O4—C32—H32B	110.1
C13—C12—C11	122.3 (2)	C33—C32—H32B	110.1
C13—C12—H12	118.8	H32A—C32—H32B	108.4
C11—C12—H12	118.8	C32—C33—H33A	109.5
C12—C13—C14	121.4 (2)	C32—C33—H33B	109.5
C12—C13—H13	119.3	H33A—C33—H33B	109.5
C14—C13—H13	119.3	C32—C33—H33C	109.5
C15—C14—C19	116.0 (2)	H33A—C33—H33C	109.5
C15—C14—C13	115.6 (2)	H33B—C33—H33C	109.5
C19—C14—C13	128.4 (2)
C8—N1—C2—C16	75.7 (2)	C10—C15—C16—C2	5.9 (2)
C5—N1—C2—C16	−158.26 (15)	C14—C15—C16—C2	−175.85 (18)
C8—N1—C2—C3	−161.45 (15)	N1—C2—C16—C17	46.3 (3)
C5—N1—C2—C3	−35.42 (16)	C3—C2—C16—C17	−69.4 (3)
C8—N1—C2—C9	−43.3 (2)	C9—C2—C16—C17	173.1 (2)
C5—N1—C2—C9	82.75 (18)	N1—C2—C16—C15	−136.11 (16)
N1—C2—C3—C27	−78.79 (16)	C3—C2—C16—C15	108.14 (16)
C16—C2—C3—C27	45.84 (19)	C9—C2—C16—C15	−9.28 (19)
C9—C2—C3—C27	158.32 (15)	C15—C16—C17—C18	−2.6 (3)
N1—C2—C3—C4	43.51 (15)	C2—C16—C17—C18	174.80 (19)
C16—C2—C3—C4	168.13 (14)	C16—C17—C18—C19	0.8 (3)
C9—C2—C3—C4	−79.38 (16)	C17—C18—C19—C14	1.7 (4)
N1—C2—C3—C20	167.60 (15)	C15—C14—C19—C18	−2.1 (3)
C16—C2—C3—C20	−67.77 (19)	C13—C14—C19—C18	176.9 (2)
C9—C2—C3—C20	44.7 (2)	C27—C3—C20—O2	168.2 (2)
C27—C3—C4—C31	−41.2 (2)	C4—C3—C20—O2	42.4 (3)
C20—C3—C4—C31	77.8 (2)	C2—C3—C20—O2	−72.9 (2)
C2—C3—C4—C31	−160.73 (15)	C27—C3—C20—C21	−11.13 (19)
C27—C3—C4—C5	83.26 (18)	C4—C3—C20—C21	−136.84 (16)
C20—C3—C4—C5	−157.78 (15)	C2—C3—C20—C21	107.85 (17)
C2—C3—C4—C5	−36.32 (16)	O2—C20—C21—C22	7.4 (4)
C2—N1—C5—C6	−114.25 (17)	C3—C20—C21—C22	−173.4 (2)
C8—N1—C5—C6	17.1 (2)	O2—C20—C21—C26	−170.3 (2)
C2—N1—C5—C4	12.88 (18)	C3—C20—C21—C26	9.0 (2)
C8—N1—C5—C4	144.27 (16)	C26—C21—C22—C23	−0.6 (3)
C31—C4—C5—N1	138.91 (16)	C20—C21—C22—C23	−178.0 (2)
C3—C4—C5—N1	15.98 (18)	C21—C22—C23—C24	1.2 (4)
C31—C4—C5—C6	−102.7 (2)	C22—C23—C24—C25	−0.2 (4)
C3—C4—C5—C6	134.33 (18)	C23—C24—C25—C26	−1.3 (3)
N1—C5—C6—C7	−31.2 (2)	C23—C24—C25—C30	178.3 (2)
C4—C5—C6—C7	−149.3 (2)	C22—C21—C26—C27	179.03 (19)
C5—C6—C7—C8	34.0 (3)	C20—C21—C26—C27	−2.9 (2)
C2—N1—C8—C7	130.8 (2)	C22—C21—C26—C25	−1.0 (3)
C5—N1—C8—C7	4.2 (2)	C20—C21—C26—C25	177.05 (17)
C6—C7—C8—N1	−24.3 (3)	C30—C25—C26—C21	−177.72 (18)
N1—C2—C9—O1	−41.3 (3)	C24—C25—C26—C21	2.0 (3)
C16—C2—C9—O1	−168.1 (2)	C30—C25—C26—C27	2.2 (3)
C3—C2—C9—O1	71.7 (3)	C24—C25—C26—C27	−178.10 (19)
N1—C2—C9—C10	136.51 (17)	C21—C26—C27—C28	177.03 (17)
C16—C2—C9—C10	9.77 (19)	C25—C26—C27—C28	−2.9 (3)
C3—C2—C9—C10	−110.44 (17)	C21—C26—C27—C3	−4.6 (2)
O1—C9—C10—C11	−5.7 (4)	C25—C26—C27—C3	175.44 (16)
C2—C9—C10—C11	176.5 (2)	C4—C3—C27—C28	−46.0 (3)
O1—C9—C10—C15	170.8 (2)	C20—C3—C27—C28	−172.5 (2)
C2—C9—C10—C15	−6.9 (2)	C2—C3—C27—C28	67.8 (3)
C15—C10—C11—C12	1.1 (3)	C4—C3—C27—C26	135.92 (16)
C9—C10—C11—C12	177.3 (2)	C20—C3—C27—C26	9.51 (19)
C10—C11—C12—C13	−0.9 (4)	C2—C3—C27—C26	−110.24 (16)
C11—C12—C13—C14	−0.2 (4)	C26—C27—C28—C29	1.8 (3)
C12—C13—C14—C15	1.0 (3)	C3—C27—C28—C29	−176.04 (18)
C12—C13—C14—C19	−178.0 (2)	C27—C28—C29—C30	−0.3 (3)
C11—C10—C15—C16	177.98 (19)	C28—C29—C30—C25	−0.4 (3)
C9—C10—C15—C16	0.9 (2)	C26—C25—C30—C29	−0.5 (3)
C11—C10—C15—C14	−0.3 (3)	C24—C25—C30—C29	179.8 (2)
C9—C10—C15—C14	−177.38 (18)	C32—O4—C31—O3	−5.6 (3)
C19—C14—C15—C10	178.4 (2)	C32—O4—C31—C4	173.5 (2)
C13—C14—C15—C10	−0.8 (3)	C5—C4—C31—O3	13.6 (3)
C19—C14—C15—C16	0.3 (3)	C3—C4—C31—O3	131.7 (2)
C13—C14—C15—C16	−178.9 (2)	C5—C4—C31—O4	−165.45 (16)
C10—C15—C16—C17	−176.17 (17)	C3—C4—C31—O4	−47.3 (2)
C14—C15—C16—C17	2.1 (3)	C31—O4—C32—C33	−169.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1	0.97	2.57	3.214 (3)	124
C23—H23···O2^i	0.93	2.35	3.162 (3)	146

Symmetry code: (i) −x+1, y+1/2, −z+1/2.