Triterpenoide. XX. 3β-Acetoxy-12-oxo-18β-olean- und 3β-Acetoxy-12,19-dioxo-9(11),13(18)-oleandien-28-säure-methyl­ester

The structures of methyl 3β-acetoxy-12-oxo-18β-olean-28-oate [C₃₃H₅₂O₅, (I)] and methyl 3β-acetoxy-12,19-dioxoolean-9(11),13(18)-dien-28-oate [C₃₃H₄₆O₆, (II)] are described. In (I), all rings are in the chair conformation, rings D and E are cis and the other rings trans-fused. In compound (II), only rings A and E are in the chair conformation, ring B has a distorted chair conformation, ring C a distorted half-boat and ring D an insignificantly distorted half-chair conformation.

S1. Comment

Anknüpfend an vorangehende Publikationen (Gzella, 1999, 2000) über Kristallstrukturen von 2-, 3-, 11-Monooxo- und 3,11-Dioxo-Derivaten von Oleanolsäure-methylesterabkömmlingen, wird in dieser Mitteilung über Kristallstrukturen von zwei weiteren im Titel erwähnten Triterpenketonen, (I) und (II), mit Carbonylgruppen in 12- bzw. 12- und 19-Stellung berichtet. \sch

In der unabhängigen Einheit der Elementarzelle von 3β-Acetoxy-12-oxo-18β-olean-28 − säure-methylester, (I), befinden sich zwei Moleküle A und B, die sich gering voneinander unterscheiden. Mit Hilfe der kleinsten Quadrate-Anpassung (Spek, 1998) wurde eine gewogene r.m.s. Abweichung von 0,676 Å gefunden. Die maximalen Abweichungen beziehen sich auf die Atome der Acetylgruppen und betragen 0,962 (C31), 1,137 (O2) und 1,150 Å (C32).

Bei Verbindung (I) weisen die erhöhten Verschiebungsfaktoren der Atome C31B, C32B, O1B, O2B (C3-Acetoxygruppe), C33A, O4A, O5A, C33B, O5B (C17-Estergruppe), C29A, C30A, C23B, C29B, C30B (Methylgruppen), C2B, C3B (Ring A) C21A, C22A (Ring E) auf Fehlordnung und/bzw. thermische Schwingungen der erwähnten Atome hin. Das betrifft besonders die Atome der C3-Acetoxygruppe [U_äq: 0,177 (3), 0,264 (6), 0,1455 (13) und 0,217 (2) Ų] und die Atome C33A und C33B [U_äq: 0,176 (3) und 0,148 (2) Ų]. Im Zusammenhang damit und wahrscheinlich auch infolge der nicht befriedigenden Kristallqualität treten größere Unterschiede in den geometrischen Parametern der Moleküle A und B von (I) auf (Tabelle 1, Experimentelles).

Die Atome C31, C32, O1 und O2 der β-orientierten Acetoxygruppe in C3-Stellung sind in beiden Verbindungen koplanar. Die Carbonylgruppe C31═O2 nimmt in beiden Fällen eine synperiplanare Stellung zur C3—O1 Bindung und eine Mittellage zwischen synklinaler und antiklinaler Stellung zur C2—C3 Bindung ein. Die Torsionswinkel C3—O1—C31—O2 und C2—C3···C31—O2 weisen in (I) folgende Werte auf: −2,1(3), −7,9(11) (Molekül A und B) und 71,1(2), 87,5(7)° (Molekül A und B), in (II) 1.1 (3) und 79.09 (18)°.

In (I) ist die C12═O3 Bindungslänge [Molekül A 1,218 (3) und Molekül B 1,209 (3) Å] der Carbonylgruppe im gesättigten C Ring mit entsprechenden Literaturdaten [1,211 (1) Å; Allen et al., 1987] vergleichbar. Alle Ringe weisen in (I) Sesselkonformation auf, wobei sich eine Deformation des Ringes C [Cremer & Pople (1975) Puckering-Parameter: Q = 0,580 (3) Å, θ = 23,6(3)°, ϕ = 334,3(6)°; Q = 0,566 (2) Å, θ = 23,9(3)°, ϕ = 325.2 (7)°; Molekül A und B] durch die oben erwähnte Carbonylgruppe beobachten läßt. Die Ringe D/E sind cis [Interplanarwinkel: 59,49 (13) und 59,44 (7)°; Molekül A und B], die übrigen trans verknüpft.

In den Ringen C, D und E von 3β-Acetoxy-12,19-dioxo-9(11),13 (18)-oleandien-28 − säure-methylester, (II), befinden sich zwei α,β ungesättigte Carbonylgruppen C12═O3 und C19═O4. Im zentralen Teil des Moleküls von (II) sind drei konjugierte Fragmente zu berücksichtigen und zwar das gänzlich planare C9═C11—C12═O3 [r.m.s. = 0.0003 Å], das annähernd flache O3═C12—C13═C18 [r.m.s. = 0.0733 Å] und das stark gefaltete System C13═C18—C19═O4 [r.m.s. = 0.1813 Å]. Demzufolge beteiligt sich die C19═O4 Carbonylgruppe nicht an der Konjugation des zuletzt erwähnten Systems, die C12═O3 Carbonylgruppe dagegen stark an der Konjugation des ersten, aber nur schwach an der Konjugation des zweiten Systems. Übereinstimmend damit ist die Bindungslänge C18—C19 [1,503 (2) Å] mit den Literaturdaten für die Csp²—Csp³ Bindung [1,509 (1) Å; Allen et al., 1987] vergleichbar, die Bindungslänge C11—C12 [1,454 (2) Å] um etwa 5σ kürzer und die Bindungslänge von C12—C13 [1,489 (2) Å] um etwa 11σ länger als die Literatur-Einfachbindung vom Typ (C═)Csp²—Csp²(═O) [1,465 (1) Å; Allen et al., 1987]. Auch die Atomabstände in den beiden Carbonylgruppen weisen entsprechende Unterschiede auf. In der C19═O4 Gruppe [1,1918 (19) Å] ist dieser um etwa 11σ kürzer als in der C12═O3 Gruppe [1,2202 (19) Å]. Im Fragment des Moleküls von (II) mit den Atomen O3, C12, C13, C18, C19 und O4 weichen die endständigen Sauerstoffatome O3 und O4 von der beinaheflachen Ebene der übrigen erwähnten Kohlenstoffatome um O,544 (3) und −1,011 (2) Å ab. Der Torsionswinkel O3—C12···C19—O4 beträgt 84,25 (16)° und der O3···O4 Atomenabstand 2,935 (2) Å.

Der Einfluß der hybridisierten Atome C9, C11, C12, C13, C18, C19, O3 und O4 im oben diskutierten Fragment auf die Konformation des Moleküls von (II) beschränkt sich auf die Ringe B, C und D. Der Ring B liegt in einer in Richtung zum sp² hybridisierten C9 Atom hin deformierter Sesselform vor [Cremer & Pople Puckering-Parameter: Q = 0,542 (2) Å, θ = 24,8(2)°, ϕ = 13,5(4)°]. Der Ring C nimmt eine verzerrte Halbboot-Konformation [Cremer & Pople Puckering-Parameter: Q = 0,489 (2) Å, θ = 54,4(2)°, ϕ = 309,2(2)%], der Ring D eine gering deformierte Halbsessel-Konformation ein [Cremer & Pople Puckering-Parameter: Q = 0,458 (2) Å, θ = 125,3(3)°, ϕ = 326,3(2)°]. Der Ring E mit den sp² hybridisierten C18 und C19 Atomen zeigt, ähnlich wie der gesättigte Ring A, Sessel-Konformation [Cremer & Pople Puckering-Parameter: Q = 0,543 (2) Å, θ = 0,9(2)°, ϕ = 212 (9)° (Ring E); Q = 0,566 (2) Å, θ = 8,3(2), ϕ = 65,0(13)° (Ring A)].

Die Atome C28, C33, O4 und O5 in (I) und C28, C33, O5 und O6 in (II) der am C17 haftenden Estergruppe sind koplanar. Aus den Torsionswinkeln C18—C17—C28—O4 [Verbindung (I): −21,1(5), −24,3(4)°, Molekül A und B] bzw. C18—C17—C28—O5 [Verbindung (II): −136,23 (18)°] geht hervor, daß die Carbonylgruppe C28═O4 in (I) eine Mittellage zwischen synperiplanarer und synklinaler, die Carbonylgruppe C28═O5 in (II) eine Mittellage zwischen antiklinaler und antiperiplanarer Stellung zur C17—C18 Bindung einnimmt.

Aus den auffallend großen Interplanarwinkeln A/B 15,90 (4), B/C 17,60 (6), C/D 20,49 (6) und D/E 25,89 (7)° von (II) kann gefolgert werden, daß das Molekül dieser Verbindung über die Ringe A bis E im Kristallnetz stark gefaltet ist.

In den Verbindungen (I) und (II) ließen sich intramolekulare kurze H···H und C—H···O Kontakte nachweisen. Im Molekül A von (I) wurden 12, im Molekül B derselben Verbindung 14 und in (II) acht H···H Kontakte aufgefunden. Die intramolekularen kurzen C—H···O Kontakte wurden in den Tabellen 2 und 3 als nicht-konventionelle Wasserstoffbrückenbindungen zusammengestellt. In den Verbindungen (I) und (II) wurden außerdem intermolekulare kurze C—H···O Kontakte beobachtet, an denen sich die Carbonylgruppen C31═O2 von (I) (beide Moleküle), C12═O3 und C19═O4 von (II) beteiligen (Tabelle 2 und 3).

S2. Experimental

Die Herstellung der Titel Verbindungen, (I) und (II), wurde von Zaprutko (2000) beschrieben.

S3. Refinement

In beiden Verbindungen wurden alle H-Atome aus Differenz-Fourier-Synthesen ermittelt, ausgenommen die H-Atome der C33A– und C32B-Methylgruppen von (I). Letztere wurden geometrisch berechnet. Alle H-Atome wurden mit Hilfe des Reitermodells verfeinert; U_iso(H) = 1,2U_äq(C). Die H-Atome der Methylgruppen wurden als starre, rotierende Gruppen verfeinert. Bei der Bestimmung der absoluten Konfiguration von (I) bzw. (II) wurden 4353 bzw. 2445 Friedel-Reflexenpaare ausgewertet. Der Ursprung für Verbindung (II) wurde nach der Methode von Flack & Schwarzenbach (1988) festgelegt. Die minimalen H···H Atom-Abstände betragen 1,95 [Molekül A, (I)] bzw. 1,98 Å [Molekül B, (I); (II)].

Computing details

For both compounds, data collection: KM-4 Software (Kuma Diffraction, 1991); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) for (I); ORTEPII (Johnson, 1976) for (II). For both compounds, software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Abb. 1. Molekülstruktur von (I), (a) Molekül A, (b) Molekül B; Wahrscheinlichkeitsniveau der Ellipsoide 30%.
	Fig. 2. Abb. 2. Molekülstruktur von (II); Wahrscheinlichkeitsniveau der Ellipsoide 50%.

(I) Methyl 3β-acetoxy-12-oxo-18β-olean-28-oate

Crystal data

C33H52O5	Dx = 1.121 Mg m^−3
Mr = 528.75	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121	Cell parameters from 46 reflections
a = 7.0662 (16) Å	θ = 12.6–26.3°
b = 22.083 (3) Å	µ = 0.58 mm^−1
c = 40.141 (5) Å	T = 293 K
V = 6263.7 (18) Å^3	Needle, colourless
Z = 8	0.50 × 0.14 × 0.09 mm
F(000) = 2320

Data collection

Kuma Diffraction KM-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 65.1°, θmin = 2.2°
Graphite monochromator	h = −7→7
ω/2θ scans	k = 0→25
10738 measured reflections	l = 0→47
10265 independent reflections	2 standard reflections every 100 reflections
7013 reflections with I > 2σ(I)	intensity decay: 11.3%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0813P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.130	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.20 e Å^−3
10265 reflections	Δρmin = −0.18 e Å^−3
704 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00025 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (2)

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
O1A	0.4257 (2)	0.25620 (7)	0.05032 (4)	0.0597 (4)
O2a	0.3864 (3)	0.28635 (10)	0.10255 (5)	0.0936 (6)
O3A	0.1264 (3)	−0.10117 (9)	0.12945 (5)	0.0889 (6)
O4A	0.2997 (5)	−0.25256 (14)	0.05773 (8)	0.1321 (10)
O5A	0.5927 (5)	−0.27344 (12)	0.04357 (7)	0.1301 (10)
C1A	0.2323 (3)	0.10562 (11)	0.07847 (6)	0.0621 (6)
H1A	0.1033	0.0916	0.0813	0.075*
H1B	0.2931	0.1047	0.1001	0.075*
C2A	0.2287 (3)	0.17072 (11)	0.06593 (6)	0.0631 (6)
H2A	0.1599	0.1727	0.0451	0.076*
H2B	0.1641	0.1962	0.0820	0.076*
C3A	0.4284 (3)	0.19339 (11)	0.06084 (6)	0.0549 (5)
H3A	0.4949	0.1911	0.0822	0.066*
C4A	0.5409 (3)	0.15687 (10)	0.03526 (5)	0.0522 (5)
C5A	0.5349 (3)	0.09001 (10)	0.04694 (5)	0.0511 (5)
H5A	0.6008	0.0903	0.0684	0.061*
C6A	0.6486 (3)	0.04619 (11)	0.02571 (6)	0.0609 (6)
H6A	0.5788	0.0371	0.0055	0.073*
H6B	0.7672	0.0651	0.0194	0.073*
C7A	0.6892 (3)	−0.01221 (11)	0.04423 (7)	0.0643 (6)
H7A	0.7717	−0.0033	0.0629	0.077*
H7B	0.7568	−0.0394	0.0295	0.077*
C8A	0.5109 (3)	−0.04485 (10)	0.05735 (6)	0.0557 (6)
C9A	0.3806 (3)	0.00212 (10)	0.07449 (6)	0.0534 (5)
H9A	0.4515	0.0153	0.0942	0.064*
C10A	0.3368 (3)	0.06210 (11)	0.05500 (6)	0.0538 (5)
C11A	0.2026 (3)	−0.02887 (11)	0.08859 (7)	0.0661 (7)
H11A	0.1407	−0.0007	0.1036	0.079*
H11B	0.1163	−0.0364	0.0703	0.079*
C12A	0.2329 (3)	−0.08725 (11)	0.10683 (7)	0.0636 (6)
C13A	0.3850 (4)	−0.12913 (11)	0.09435 (6)	0.0608 (6)
H13A	0.3361	−0.1436	0.0729	0.073*
C14A	0.5676 (3)	−0.09381 (11)	0.08484 (6)	0.0580 (6)
C15A	0.7142 (4)	−0.13912 (12)	0.07077 (7)	0.0721 (7)
H15A	0.6760	−0.1506	0.0484	0.087*
H15B	0.8357	−0.1189	0.0691	0.087*
C16A	0.7382 (4)	−0.19603 (13)	0.09144 (9)	0.0846 (9)
H16A	0.7911	−0.1853	0.1129	0.102*
H16B	0.8271	−0.2228	0.0804	0.102*
C17A	0.5495 (4)	−0.22991 (12)	0.09680 (8)	0.0802 (8)
C18A	0.4098 (4)	−0.18741 (11)	0.11504 (7)	0.0700 (7)
H18A	0.2869	−0.2080	0.1147	0.084*
C19A	0.4607 (4)	−0.17893 (13)	0.15148 (7)	0.0811 (8)
H19A	0.3668	−0.1529	0.1617	0.097*
H19B	0.5818	−0.1584	0.1528	0.097*
C20A	0.4725 (6)	−0.23781 (15)	0.17136 (8)	0.0984 (11)
C21A	0.6193 (6)	−0.27842 (17)	0.15384 (10)	0.1151 (13)
H21A	0.7432	−0.2599	0.1560	0.138*
H21B	0.6235	−0.3173	0.1651	0.138*
C22A	0.5790 (6)	−0.28859 (14)	0.11809 (10)	0.1107 (13)
H22A	0.4660	−0.3133	0.1163	0.133*
H22B	0.6829	−0.3115	0.1086	0.133*
C23A	0.7467 (3)	0.17965 (12)	0.03700 (7)	0.0652 (6)
H23A	0.7488	0.2228	0.0341	0.078*
H23B	0.8197	0.1609	0.0197	0.078*
H23C	0.7998	0.1695	0.0583	0.078*
C24A	0.4685 (4)	0.16767 (12)	−0.00013 (6)	0.0657 (6)
H24A	0.3332	0.1638	−0.0005	0.079*
H24B	0.5234	0.1383	−0.0149	0.079*
H24C	0.5033	0.2077	−0.0072	0.079*
C25A	0.2121 (4)	0.05261 (12)	0.02414 (7)	0.0697 (7)
H25A	0.1172	0.0227	0.0289	0.084*
H25B	0.2890	0.0390	0.0059	0.084*
H25C	0.1520	0.0901	0.0183	0.084*
C26A	0.4139 (4)	−0.07485 (13)	0.02723 (6)	0.0738 (7)
H26A	0.4191	−0.0480	0.0085	0.089*
H26B	0.2842	−0.0833	0.0326	0.089*
H26C	0.4779	−0.1119	0.0219	0.089*
C27A	0.6512 (4)	−0.06277 (12)	0.11610 (7)	0.0683 (7)
H27A	0.7329	−0.0906	0.1275	0.082*
H27B	0.5502	−0.0507	0.1307	0.082*
H27C	0.7222	−0.0277	0.1095	0.082*
C28A	0.4645 (7)	−0.25178 (14)	0.06431 (9)	0.0943 (10)
C29A	0.5409 (8)	−0.2239 (2)	0.20643 (9)	0.1384 (18)
H29A	0.4473	−0.2001	0.2178	0.166*
H29B	0.6574	−0.2016	0.2053	0.166*
H29C	0.5612	−0.2611	0.2183	0.166*
C30A	0.2818 (7)	−0.26909 (17)	0.17396 (10)	0.1212 (14)
H30A	0.2941	−0.3049	0.1873	0.145*
H30B	0.2386	−0.2800	0.1521	0.145*
H30C	0.1921	−0.2421	0.1841	0.145*
C31A	0.4065 (4)	0.29817 (12)	0.07359 (7)	0.0661 (7)
C32A	0.4179 (5)	0.36040 (12)	0.06009 (8)	0.0867 (8)
H32A	0.3032	0.3697	0.0483	0.104*
H32B	0.5234	0.3633	0.0451	0.104*
H32C	0.4344	0.3886	0.0781	0.104*
C33A	0.5246 (10)	−0.2989 (2)	0.01258 (12)	0.176 (3)
H33A	0.4199	−0.3254	0.0170	0.211*
H33B	0.6245	−0.3214	0.0021	0.211*
H33C	0.4844	−0.2669	−0.0019	0.211*
O1B	1.0702 (5)	−0.96338 (11)	0.20038 (7)	0.1455 (13)
O2B	1.3473 (8)	−0.9789 (2)	0.17819 (14)	0.217 (2)
O3B	0.8790 (4)	−0.63328 (9)	0.08424 (4)	0.0903 (6)
O4B	0.5450 (3)	−0.49440 (11)	0.15137 (6)	0.0981 (7)
O5B	0.6756 (3)	−0.45695 (14)	0.19632 (6)	0.1219 (10)
C1B	0.9359 (5)	−0.83188 (12)	0.14611 (7)	0.0833 (9)
H1C	0.8521	−0.8300	0.1270	0.100*
H1D	1.0617	−0.8205	0.1387	0.100*
C2B	0.9410 (6)	−0.89676 (15)	0.15921 (8)	0.1056 (12)
H2C	0.8139	−0.9096	0.1649	0.127*
H2D	0.9885	−0.9235	0.1420	0.127*
C3B	1.0661 (6)	−0.90107 (15)	0.18949 (9)	0.1022 (12)
H3B	1.1947	−0.8890	0.1832	0.123*
C4B	1.0022 (5)	−0.86193 (14)	0.21843 (7)	0.0832 (8)
C5B	0.9868 (4)	−0.79626 (12)	0.20480 (6)	0.0688 (7)
H5B	1.1162	−0.7863	0.1980	0.083*
C6B	0.9407 (4)	−0.74945 (14)	0.23099 (6)	0.0761 (8)
H6C	1.0131	−0.7579	0.2510	0.091*
H6D	0.8074	−0.7519	0.2366	0.091*
C7B	0.9860 (4)	−0.68606 (13)	0.21889 (6)	0.0702 (7)
H7C	1.1222	−0.6823	0.2166	0.084*
H7D	0.9458	−0.6573	0.2357	0.084*
C8B	0.8935 (3)	−0.66890 (11)	0.18572 (5)	0.0557 (6)
C9B	0.9194 (3)	−0.72118 (11)	0.16055 (6)	0.0585 (6)
H9B	1.0563	−0.7229	0.1568	0.070*
C10B	0.8674 (4)	−0.78592 (12)	0.17275 (6)	0.0659 (6)
C11B	0.8373 (5)	−0.70527 (12)	0.12670 (6)	0.0743 (8)
H11C	0.8891	−0.7334	0.1105	0.089*
H11D	0.7018	−0.7122	0.1276	0.089*
C12B	0.8692 (4)	−0.64224 (12)	0.11391 (6)	0.0637 (6)
C13B	0.8714 (3)	−0.59156 (11)	0.13928 (5)	0.0562 (6)
H13B	0.7407	−0.5902	0.1474	0.067*
C14B	0.9870 (3)	−0.61032 (11)	0.17036 (5)	0.0543 (6)
C15B	0.9898 (3)	−0.55760 (12)	0.19551 (6)	0.0647 (6)
H15C	0.8690	−0.5565	0.2070	0.078*
H15D	1.0867	−0.5656	0.2120	0.078*
C16B	1.0263 (3)	−0.49614 (12)	0.18039 (6)	0.0636 (6)
H16C	1.1538	−0.4952	0.1714	0.076*
H16D	1.0183	−0.4656	0.1977	0.076*
C17B	0.8864 (4)	−0.48045 (11)	0.15269 (7)	0.0643 (6)
C18B	0.9039 (4)	−0.52792 (11)	0.12487 (6)	0.0630 (6)
H18B	0.7985	−0.5204	0.1096	0.076*
C19B	1.0857 (4)	−0.51840 (12)	0.10450 (6)	0.0738 (7)
H19C	1.1939	−0.5266	0.1187	0.089*
H19D	1.0879	−0.5474	0.0864	0.089*
C20B	1.1057 (6)	−0.45480 (14)	0.09005 (8)	0.0910 (9)
C21B	1.0982 (5)	−0.40955 (13)	0.11831 (8)	0.0905 (9)
H21C	1.1032	−0.3689	0.1092	0.109*
H21D	1.2084	−0.4150	0.1324	0.109*
C22B	0.9190 (5)	−0.41604 (13)	0.13955 (8)	0.0849 (8)
H22C	0.8105	−0.4040	0.1263	0.102*
H22D	0.9275	−0.3885	0.1583	0.102*
C23B	1.1585 (6)	−0.86436 (18)	0.24507 (10)	0.1200 (13)
H23D	1.1865	−0.9058	0.2503	0.144*
H23E	1.1162	−0.8439	0.2648	0.144*
H23F	1.2704	−0.8449	0.2367	0.144*
C24B	0.8185 (6)	−0.88593 (15)	0.23389 (8)	0.0976 (11)
H24D	0.7261	−0.8920	0.2167	0.117*
H24E	0.7712	−0.8571	0.2497	0.117*
H24F	0.8431	−0.9237	0.2449	0.117*
C25B	0.6539 (4)	−0.79569 (14)	0.17764 (8)	0.0847 (8)
H25D	0.6264	−0.8382	0.1770	0.102*
H25E	0.5858	−0.7755	0.1602	0.102*
H25F	0.6162	−0.7794	0.1988	0.102*
C26B	0.6806 (4)	−0.65751 (13)	0.19327 (7)	0.0748 (7)
H26D	0.6374	−0.6862	0.2095	0.090*
H26E	0.6084	−0.6621	0.1732	0.090*
H26F	0.6646	−0.6172	0.2018	0.090*
C27B	1.1964 (3)	−0.62222 (12)	0.16039 (6)	0.0638 (6)
H27D	1.2632	−0.5844	0.1592	0.077*
H27E	1.2003	−0.6418	0.1390	0.077*
H27F	1.2549	−0.6478	0.1768	0.077*
C28B	0.6841 (4)	−0.47899 (13)	0.16603 (8)	0.0745 (8)
C29B	1.2974 (7)	−0.45016 (19)	0.07301 (10)	0.1288 (16)
H29D	1.3134	−0.4101	0.0642	0.155*
H29E	1.3041	−0.4791	0.0552	0.155*
H29F	1.3958	−0.4583	0.0889	0.155*
C30B	0.9489 (8)	−0.44198 (17)	0.06432 (9)	0.1265 (15)
H30D	0.9646	−0.4019	0.0555	0.152*
H30E	0.8274	−0.4451	0.0749	0.152*
H30F	0.9570	−0.4709	0.0465	0.152*
C31B	1.2227 (13)	−0.9967 (3)	0.19477 (13)	0.177 (3)
C32B	1.2024 (15)	−1.0577 (2)	0.20881 (12)	0.264 (6)
H32D	1.1164	−1.0808	0.1953	0.317*
H32E	1.1539	−1.0549	0.2311	0.317*
H32F	1.3236	−1.0773	0.2092	0.317*
C33B	0.4868 (5)	−0.4520 (2)	0.21064 (12)	0.148 (2)
H33D	0.4050	−0.4314	0.1953	0.177*
H33E	0.4932	−0.4296	0.2311	0.177*
H33F	0.4378	−0.4918	0.2150	0.177*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0501 (9)	0.0643 (10)	0.0648 (9)	0.0060 (7)	−0.0004 (7)	0.0012 (8)
O2A	0.0986 (16)	0.1079 (15)	0.0744 (13)	0.0301 (13)	0.0023 (12)	−0.0154 (11)
O3A	0.0547 (11)	0.1003 (13)	0.1117 (14)	0.0184 (10)	0.0265 (11)	0.0398 (12)
O4A	0.117 (2)	0.143 (2)	0.137 (2)	−0.0057 (19)	0.0102 (19)	−0.0380 (18)
O5A	0.137 (2)	0.1236 (19)	0.129 (2)	−0.0030 (18)	0.0503 (19)	−0.0352 (17)
C1A	0.0342 (12)	0.0722 (15)	0.0800 (16)	0.0129 (11)	0.0142 (11)	0.0147 (13)
C2A	0.0370 (13)	0.0738 (16)	0.0784 (16)	0.0141 (11)	0.0121 (11)	0.0097 (13)
C3A	0.0388 (12)	0.0664 (14)	0.0597 (13)	0.0082 (10)	0.0028 (10)	0.0058 (11)
C4A	0.0326 (11)	0.0668 (14)	0.0572 (12)	0.0027 (9)	0.0035 (9)	0.0075 (11)
C5A	0.0279 (11)	0.0666 (14)	0.0589 (12)	0.0058 (9)	0.0033 (9)	0.0055 (11)
C6A	0.0382 (12)	0.0686 (15)	0.0760 (16)	0.0053 (10)	0.0157 (11)	0.0062 (12)
C7A	0.0394 (13)	0.0680 (15)	0.0856 (17)	0.0121 (11)	0.0198 (11)	0.0062 (13)
C8A	0.0394 (12)	0.0600 (14)	0.0677 (14)	0.0043 (10)	0.0086 (11)	0.0045 (11)
C9A	0.0282 (11)	0.0647 (14)	0.0674 (14)	0.0057 (10)	0.0066 (10)	0.0092 (11)
C10A	0.0299 (11)	0.0657 (14)	0.0658 (13)	0.0049 (10)	0.0052 (10)	0.0116 (11)
C11A	0.0349 (12)	0.0725 (15)	0.0910 (18)	0.0068 (10)	0.0138 (12)	0.0166 (14)
C12A	0.0384 (13)	0.0742 (16)	0.0781 (17)	0.0016 (11)	0.0044 (12)	0.0118 (13)
C13A	0.0489 (14)	0.0612 (14)	0.0723 (14)	0.0050 (11)	0.0062 (11)	0.0074 (12)
C14A	0.0359 (12)	0.0634 (14)	0.0747 (15)	0.0101 (10)	0.0052 (10)	0.0055 (12)
C15A	0.0496 (15)	0.0681 (16)	0.0986 (19)	0.0117 (12)	0.0170 (13)	0.0055 (14)
C16A	0.0672 (18)	0.0720 (17)	0.115 (2)	0.0252 (14)	0.0206 (17)	0.0088 (16)
C17A	0.083 (2)	0.0625 (16)	0.095 (2)	0.0167 (14)	0.0212 (17)	0.0101 (15)
C18A	0.0642 (16)	0.0632 (15)	0.0825 (17)	0.0107 (13)	0.0125 (14)	0.0120 (13)
C19A	0.083 (2)	0.0771 (18)	0.0831 (18)	0.0253 (15)	0.0107 (16)	0.0130 (15)
C20A	0.115 (3)	0.093 (2)	0.088 (2)	0.042 (2)	0.0201 (19)	0.0302 (18)
C21A	0.133 (3)	0.099 (2)	0.113 (3)	0.057 (2)	0.032 (2)	0.037 (2)
C22A	0.133 (3)	0.0743 (19)	0.125 (3)	0.042 (2)	0.044 (3)	0.0238 (19)
C23A	0.0353 (12)	0.0735 (15)	0.0869 (17)	0.0009 (11)	0.0056 (12)	0.0073 (14)
C24A	0.0556 (15)	0.0772 (16)	0.0645 (14)	0.0057 (12)	0.0054 (12)	0.0087 (12)
C25A	0.0398 (13)	0.0808 (17)	0.0883 (19)	0.0024 (12)	−0.0069 (12)	0.0206 (15)
C26A	0.0710 (17)	0.0796 (17)	0.0708 (16)	0.0046 (14)	0.0036 (14)	0.0011 (13)
C27A	0.0458 (14)	0.0744 (16)	0.0846 (17)	0.0132 (12)	−0.0063 (13)	0.0085 (14)
C28A	0.111 (3)	0.0692 (18)	0.102 (2)	0.0039 (19)	0.030 (2)	−0.0028 (17)
C29A	0.174 (5)	0.144 (3)	0.097 (3)	0.059 (3)	0.011 (3)	0.039 (3)
C30A	0.136 (4)	0.097 (2)	0.131 (3)	0.021 (2)	0.047 (3)	0.035 (2)
C31A	0.0447 (14)	0.0794 (17)	0.0742 (17)	0.0138 (12)	−0.0075 (12)	−0.0082 (15)
C32A	0.0756 (19)	0.0739 (18)	0.111 (2)	0.0113 (15)	−0.0145 (18)	−0.0104 (17)
C33A	0.214 (7)	0.174 (5)	0.138 (4)	−0.038 (4)	0.062 (4)	−0.071 (4)
O1B	0.208 (3)	0.0907 (16)	0.138 (2)	0.059 (2)	0.077 (2)	0.0451 (15)
O2B	0.222 (5)	0.183 (4)	0.245 (5)	0.125 (4)	0.059 (4)	0.015 (4)
O3B	0.1343 (19)	0.0833 (12)	0.0534 (10)	−0.0002 (12)	−0.0190 (11)	−0.0017 (9)
O4B	0.0534 (12)	0.1265 (17)	0.1146 (16)	0.0142 (11)	−0.0160 (12)	−0.0260 (14)
O5B	0.0444 (11)	0.190 (3)	0.1316 (19)	0.0092 (13)	0.0064 (12)	−0.0880 (19)
C1B	0.111 (2)	0.0700 (17)	0.0686 (16)	0.0094 (16)	0.0210 (16)	0.0042 (14)
C2B	0.153 (4)	0.077 (2)	0.087 (2)	0.014 (2)	0.043 (2)	0.0032 (17)
C3B	0.122 (3)	0.087 (2)	0.097 (2)	0.033 (2)	0.045 (2)	0.0322 (18)
C4B	0.082 (2)	0.092 (2)	0.0756 (17)	0.0147 (16)	0.0221 (16)	0.0261 (16)
C5B	0.0556 (15)	0.0864 (18)	0.0644 (14)	0.0110 (13)	0.0122 (12)	0.0168 (13)
C6B	0.0701 (18)	0.104 (2)	0.0542 (13)	0.0061 (16)	0.0054 (12)	0.0122 (14)
C7B	0.0651 (17)	0.0930 (18)	0.0524 (13)	0.0092 (14)	−0.0009 (12)	0.0021 (13)
C8B	0.0390 (12)	0.0743 (15)	0.0539 (12)	0.0102 (10)	0.0016 (10)	−0.0018 (11)
C9B	0.0525 (13)	0.0707 (15)	0.0523 (12)	0.0088 (11)	0.0019 (10)	0.0009 (11)
C10B	0.0612 (15)	0.0751 (16)	0.0613 (14)	0.0073 (12)	0.0080 (12)	0.0031 (12)
C11B	0.093 (2)	0.0700 (16)	0.0604 (15)	0.0053 (14)	−0.0125 (14)	−0.0062 (13)
C12B	0.0638 (16)	0.0725 (16)	0.0549 (14)	0.0098 (13)	−0.0156 (12)	−0.0040 (12)
C13B	0.0465 (13)	0.0673 (14)	0.0548 (12)	0.0134 (10)	−0.0086 (10)	−0.0058 (11)
C14B	0.0384 (12)	0.0707 (15)	0.0538 (12)	0.0104 (10)	−0.0027 (10)	−0.0038 (11)
C15B	0.0488 (13)	0.0893 (18)	0.0561 (13)	0.0050 (13)	−0.0043 (11)	−0.0122 (13)
C16B	0.0470 (13)	0.0759 (16)	0.0681 (14)	0.0080 (11)	−0.0040 (11)	−0.0176 (13)
C17B	0.0493 (14)	0.0690 (15)	0.0748 (15)	0.0144 (11)	−0.0054 (12)	−0.0095 (13)
C18B	0.0569 (15)	0.0693 (15)	0.0627 (14)	0.0140 (12)	−0.0094 (12)	−0.0084 (12)
C19B	0.0850 (19)	0.0716 (16)	0.0646 (15)	0.0106 (14)	0.0024 (14)	−0.0058 (13)
C20B	0.122 (3)	0.0780 (19)	0.0726 (18)	0.0064 (18)	0.0084 (19)	0.0082 (15)
C21B	0.104 (2)	0.0674 (17)	0.100 (2)	0.0031 (17)	0.0026 (19)	0.0027 (16)
C22B	0.082 (2)	0.0723 (18)	0.101 (2)	0.0164 (15)	−0.0075 (17)	−0.0126 (16)
C23B	0.113 (3)	0.128 (3)	0.120 (3)	0.024 (2)	−0.004 (2)	0.052 (2)
C24B	0.113 (3)	0.092 (2)	0.088 (2)	0.0030 (19)	0.0430 (19)	0.0227 (18)
C25B	0.0649 (18)	0.089 (2)	0.100 (2)	−0.0082 (14)	−0.0044 (16)	0.0065 (17)
C26B	0.0444 (14)	0.0880 (19)	0.0920 (19)	0.0102 (12)	0.0111 (13)	−0.0032 (15)
C27B	0.0422 (13)	0.0803 (16)	0.0690 (15)	0.0136 (11)	0.0028 (11)	0.0070 (13)
C28B	0.0537 (17)	0.0815 (18)	0.088 (2)	0.0179 (13)	−0.0095 (14)	−0.0208 (16)
C29B	0.162 (4)	0.109 (3)	0.115 (3)	−0.014 (3)	0.051 (3)	0.012 (2)
C30B	0.193 (5)	0.094 (2)	0.093 (2)	0.013 (3)	−0.030 (3)	0.019 (2)
C31B	0.284 (9)	0.137 (4)	0.109 (3)	0.119 (6)	0.061 (4)	0.028 (3)
C32B	0.542 (16)	0.124 (4)	0.126 (3)	0.168 (7)	0.090 (6)	0.046 (3)
C33B	0.0498 (19)	0.228 (5)	0.165 (4)	0.006 (3)	0.020 (2)	−0.098 (4)

Geometric parameters (Å, º)

O1A—C31A	1.323 (3)	O1B—C31B	1.324 (7)
O1A—C3A	1.450 (3)	O1B—C3B	1.444 (4)
O2A—C31A	1.200 (3)	O2B—C31B	1.171 (8)
O3A—C12A	1.218 (3)	O3B—C12B	1.209 (3)
O4A—C28A	1.194 (5)	O4B—C28B	1.195 (3)
O5A—C28A	1.320 (4)	O5B—C28B	1.311 (3)
O5A—C33A	1.448 (5)	O5B—C33B	1.457 (4)
C1A—C2A	1.524 (4)	C1B—C2B	1.527 (4)
C1A—C10A	1.535 (3)	C1B—C10B	1.552 (4)
C2A—C3A	1.511 (3)	C2B—C3B	1.506 (6)
C3A—C4A	1.529 (3)	C3B—C4B	1.517 (4)
C4A—C24A	1.529 (3)	C4B—C24B	1.533 (5)
C4A—C23A	1.540 (3)	C4B—C23B	1.538 (5)
C4A—C5A	1.550 (3)	C4B—C5B	1.554 (4)
C5A—C6A	1.519 (3)	C5B—C6B	1.510 (4)
C5A—C10A	1.563 (3)	C5B—C10B	1.555 (4)
C6A—C7A	1.516 (3)	C6B—C7B	1.516 (4)
C7A—C8A	1.544 (3)	C7B—C8B	1.531 (3)
C8A—C26A	1.540 (4)	C8B—C9B	1.545 (3)
C8A—C9A	1.548 (3)	C8B—C26B	1.555 (3)
C8A—C14A	1.596 (3)	C8B—C14B	1.578 (3)
C9A—C11A	1.540 (3)	C9B—C11B	1.519 (3)
C9A—C10A	1.569 (3)	C9B—C10B	1.555 (4)
C10A—C25A	1.534 (3)	C10B—C25B	1.536 (4)
C11A—C12A	1.498 (4)	C11B—C12B	1.501 (4)
C12A—C13A	1.504 (3)	C12B—C13B	1.513 (3)
C13A—C18A	1.542 (3)	C13B—C18B	1.537 (4)
C13A—C14A	1.555 (3)	C13B—C14B	1.548 (3)
C14A—C27A	1.547 (3)	C14B—C15B	1.541 (3)
C14A—C15A	1.547 (3)	C14B—C27B	1.555 (3)
C15A—C16A	1.515 (4)	C15B—C16B	1.509 (4)
C16A—C17A	1.544 (5)	C16B—C17B	1.528 (4)
C17A—C28A	1.515 (5)	C17B—C28B	1.527 (4)
C17A—C18A	1.546 (4)	C17B—C22B	1.535 (4)
C17A—C22A	1.566 (4)	C17B—C18B	1.537 (3)
C18A—C19A	1.518 (4)	C18B—C19B	1.537 (4)
C19A—C20A	1.528 (4)	C19B—C20B	1.526 (4)
C20A—C30A	1.518 (6)	C20B—C21B	1.513 (4)
C20A—C29A	1.520 (5)	C20B—C29B	1.521 (6)
C20A—C21A	1.541 (5)	C20B—C30B	1.541 (5)
C21A—C22A	1.480 (6)	C21B—C22B	1.533 (5)
C31A—C32A	1.479 (4)	C31B—C32B	1.468 (7)
C31A—O1A—C3A	117.76 (19)	C31B—O1B—C3B	119.6 (4)
C28A—O5A—C33A	117.0 (4)	C28B—O5B—C33B	115.8 (3)
C2A—C1A—C10A	113.33 (19)	C2B—C1B—C10B	112.6 (2)
C3A—C2A—C1A	109.97 (18)	C3B—C2B—C1B	110.6 (3)
O1A—C3A—C2A	110.10 (18)	O1B—C3B—C2B	108.4 (3)
O1A—C3A—C4A	108.42 (17)	O1B—C3B—C4B	108.5 (2)
C2A—C3A—C4A	113.7 (2)	C2B—C3B—C4B	114.1 (3)
C3A—C4A—C24A	111.58 (18)	C3B—C4B—C24B	111.4 (3)
C3A—C4A—C23A	106.7 (2)	C3B—C4B—C23B	107.4 (3)
C24A—C4A—C23A	107.9 (2)	C24B—C4B—C23B	108.3 (2)
C3A—C4A—C5A	106.57 (17)	C3B—C4B—C5B	106.4 (2)
C24A—C4A—C5A	114.9 (2)	C24B—C4B—C5B	113.9 (3)
C23A—C4A—C5A	108.87 (18)	C23B—C4B—C5B	109.1 (3)
C6A—C5A—C4A	114.99 (17)	C6B—C5B—C4B	114.1 (2)
C6A—C5A—C10A	109.79 (18)	C6B—C5B—C10B	111.0 (2)
C4A—C5A—C10A	117.58 (17)	C4B—C5B—C10B	117.8 (2)
C7A—C6A—C5A	111.53 (19)	C5B—C6B—C7B	111.3 (2)
C6A—C7A—C8A	114.20 (18)	C6B—C7B—C8B	114.6 (2)
C26A—C8A—C7A	107.2 (2)	C7B—C8B—C9B	109.45 (19)
C26A—C8A—C9A	111.9 (2)	C7B—C8B—C26B	106.5 (2)
C7A—C8A—C9A	108.91 (18)	C9B—C8B—C26B	111.3 (2)
C26A—C8A—C14A	111.31 (19)	C7B—C8B—C14B	111.3 (2)
C7A—C8A—C14A	110.31 (19)	C9B—C8B—C14B	107.89 (17)
C9A—C8A—C14A	107.22 (18)	C26B—C8B—C14B	110.4 (2)
C11A—C9A—C8A	110.56 (19)	C11B—C9B—C8B	111.5 (2)
C11A—C9A—C10A	113.42 (17)	C11B—C9B—C10B	113.8 (2)
C8A—C9A—C10A	117.46 (18)	C8B—C9B—C10B	116.94 (19)
C25A—C10A—C1A	107.74 (19)	C25B—C10B—C1B	107.6 (3)
C25A—C10A—C5A	113.65 (19)	C25B—C10B—C5B	114.0 (2)
C1A—C10A—C5A	108.10 (19)	C1B—C10B—C5B	107.7 (2)
C25A—C10A—C9A	113.6 (2)	C25B—C10B—C9B	113.7 (2)
C1A—C10A—C9A	108.48 (18)	C1B—C10B—C9B	108.1 (2)
C5A—C10A—C9A	105.04 (16)	C5B—C10B—C9B	105.5 (2)
C12A—C11A—C9A	116.46 (19)	C12B—C11B—C9B	117.6 (2)
O3A—C12A—C11A	119.6 (2)	O3B—C12B—C11B	119.8 (2)
O3A—C12A—C13A	122.3 (2)	O3B—C12B—C13B	122.8 (2)
C11A—C12A—C13A	117.9 (2)	C11B—C12B—C13B	117.2 (2)
C12A—C13A—C18A	114.5 (2)	C12B—C13B—C18B	115.12 (19)
C12A—C13A—C14A	111.49 (19)	C12B—C13B—C14B	110.48 (19)
C18A—C13A—C14A	117.2 (2)	C18B—C13B—C14B	118.0 (2)
C27A—C14A—C15A	109.1 (2)	C15B—C14B—C13B	109.42 (18)
C27A—C14A—C13A	109.9 (2)	C15B—C14B—C27B	106.5 (2)
C15A—C14A—C13A	108.7 (2)	C13B—C14B—C27B	109.90 (19)
C27A—C14A—C8A	110.89 (19)	C15B—C14B—C8B	111.62 (18)
C15A—C14A—C8A	110.73 (19)	C13B—C14B—C8B	108.26 (19)
C13A—C14A—C8A	107.51 (18)	C27B—C14B—C8B	111.13 (18)
C16A—C15A—C14A	114.3 (2)	C16B—C15B—C14B	114.72 (19)
C15A—C16A—C17A	112.4 (2)	C15B—C16B—C17B	112.7 (2)
C28A—C17A—C16A	112.2 (3)	C28B—C17B—C16B	110.8 (2)
C28A—C17A—C18A	110.4 (3)	C28B—C17B—C22B	104.0 (2)
C16A—C17A—C18A	108.9 (2)	C16B—C17B—C22B	111.3 (2)
C28A—C17A—C22A	105.0 (3)	C28B—C17B—C18B	110.1 (2)
C16A—C17A—C22A	111.2 (3)	C16B—C17B—C18B	108.81 (19)
C18A—C17A—C22A	109.2 (2)	C22B—C17B—C18B	111.7 (2)
C19A—C18A—C13A	116.3 (2)	C17B—C18B—C13B	109.8 (2)
C19A—C18A—C17A	112.3 (2)	C17B—C18B—C19B	111.1 (2)
C13A—C18A—C17A	108.9 (2)	C13B—C18B—C19B	116.7 (2)
C18A—C19A—C20A	114.3 (3)	C20B—C19B—C18B	113.9 (2)
C30A—C20A—C29A	108.1 (3)	C21B—C20B—C29B	108.9 (3)
C30A—C20A—C19A	112.0 (3)	C21B—C20B—C19B	108.6 (2)
C29A—C20A—C19A	109.2 (3)	C29B—C20B—C19B	108.4 (3)
C30A—C20A—C21A	111.4 (3)	C21B—C20B—C30B	110.9 (3)
C29A—C20A—C21A	109.1 (3)	C29B—C20B—C30B	109.1 (3)
C19A—C20A—C21A	107.1 (3)	C19B—C20B—C30B	110.9 (3)
C22A—C21A—C20A	113.6 (3)	C20B—C21B—C22B	112.6 (3)
C21A—C22A—C17A	115.4 (3)	C21B—C22B—C17B	113.7 (2)
O4A—C28A—O5A	121.6 (4)	O4B—C28B—O5B	121.7 (3)
O4A—C28A—C17A	125.6 (3)	O4B—C28B—C17B	126.3 (3)
O5A—C28A—C17A	112.7 (4)	O5B—C28B—C17B	112.1 (2)
O2A—C31A—O1A	123.0 (3)	O2B—C31B—O1B	121.5 (5)
O2A—C31A—C32A	124.3 (3)	O2B—C31B—C32B	126.8 (6)
O1A—C31A—C32A	112.7 (2)	O1B—C31B—C32B	111.4 (7)
C10A—C1A—C2A—C3A	−57.8 (3)	C10B—C1B—C2B—C3B	−57.3 (4)
C31A—O1A—C3A—C2A	81.8 (2)	C31B—O1B—C3B—C2B	105.4 (5)
C31A—O1A—C3A—C4A	−153.3 (2)	C31B—O1B—C3B—C4B	−130.2 (5)
C1A—C2A—C3A—O1A	−177.49 (19)	C1B—C2B—C3B—O1B	−178.5 (3)
C1A—C2A—C3A—C4A	60.7 (3)	C1B—C2B—C3B—C4B	60.5 (4)
O1A—C3A—C4A—C24A	−52.2 (2)	O1B—C3B—C4B—C24B	−51.4 (4)
C2A—C3A—C4A—C24A	70.6 (3)	C2B—C3B—C4B—C24B	69.5 (3)
O1A—C3A—C4A—C23A	65.4 (2)	O1B—C3B—C4B—C23B	67.1 (4)
C2A—C3A—C4A—C23A	−171.77 (19)	C2B—C3B—C4B—C23B	−172.0 (3)
O1A—C3A—C4A—C5A	−178.32 (17)	O1B—C3B—C4B—C5B	−176.2 (3)
C2A—C3A—C4A—C5A	−55.5 (2)	C2B—C3B—C4B—C5B	−55.2 (4)
C3A—C4A—C5A—C6A	−176.78 (19)	C3B—C4B—C5B—C6B	−175.0 (3)
C24A—C4A—C5A—C6A	59.1 (2)	C24B—C4B—C5B—C6B	61.9 (4)
C23A—C4A—C5A—C6A	−62.0 (3)	C23B—C4B—C5B—C6B	−59.3 (3)
C3A—C4A—C5A—C10A	51.5 (2)	C3B—C4B—C5B—C10B	52.2 (3)
C24A—C4A—C5A—C10A	−72.6 (2)	C24B—C4B—C5B—C10B	−71.0 (3)
C3A—C4A—C5A—C10A	166.3 (2)	C23B—C4B—C5B—C10B	167.8 (2)
C4A—C5A—C6A—C7A	161.30 (19)	C4B—C5B—C6B—C7B	162.6 (2)
C10A—C5A—C6A—C7A	−63.4 (2)	C10B—C5B—C6B—C7B	−61.4 (3)
C5A—C6A—C7A—C8A	55.9 (3)	C5B—C6B—C7B—C8B	54.2 (3)
C6A—C7A—C8A—C26A	75.0 (3)	C6B—C7B—C8B—C9B	−46.1 (3)
C6A—C7A—C8A—C9A	−46.2 (3)	C6B—C7B—C8B—C26B	74.3 (3)
C6A—C7A—C8A—C14A	−163.6 (2)	C6B—C7B—C8B—C14B	−165.3 (2)
C26A—C8A—C9A—C11A	62.8 (3)	C7B—C8B—C9B—C11B	−177.5 (2)
C7A—C8A—C9A—C11A	−178.8 (2)	C26B—C8B—C9B—C11B	65.0 (3)
C14A—C8A—C9A—C11A	−59.5 (2)	C14B—C8B—C9B—C11B	−56.2 (3)
C26A—C8A—C9A—C10A	−69.5 (3)	C7B—C8B—C9B—C10B	49.0 (3)
C7A—C8A—C9A—C10A	48.8 (3)	C26B—C8B—C9B—C10B	−68.4 (3)
C14A—C8A—C9A—C10A	168.17 (18)	C14B—C8B—C9B—C10B	170.34 (19)
C2A—C1A—C10A—C25A	−72.1 (3)	C2B—C1B—C10B—C25B	−72.2 (4)
C2A—C1A—C10A—C5A	51.1 (3)	C2B—C1B—C10B—C5B	51.1 (4)
C2A—C1A—C10A—C9A	164.47 (19)	C2B—C1B—C10B—C9B	164.6 (3)
C6A—C5A—C10A—C25A	−64.5 (2)	C6B—C5B—C10B—C25B	−65.8 (3)
C4A—C5A—C10A—C25A	69.5 (3)	C4B—C5B—C10B—C25B	68.5 (3)
C6A—C5A—C10A—C1A	175.99 (18)	C6B—C5B—C10B—C1B	174.9 (2)
C4A—C5A—C10A—C1A	−50.0 (3)	C4B—C5B—C10B—C1B	−50.9 (3)
C6A—C5A—C10A—C9A	60.3 (2)	C6B—C5B—C10B—C9B	59.6 (3)
C4A—C5A—C10A—C9A	−165.69 (18)	C4B—C5B—C10B—C9B	−166.1 (2)
C11A—C9A—C10A—C25A	−62.2 (3)	C11B—C9B—C10B—C25B	−62.2 (3)
C8A—C9A—C10A—C25A	68.9 (2)	C8B—C9B—C10B—C25B	70.2 (3)
C11A—C9A—C10A—C1A	57.6 (3)	C11B—C9B—C10B—C1B	57.2 (3)
C8A—C9A—C10A—C1A	−171.35 (19)	C8B—C9B—C10B—C1B	−170.4 (2)
C11A—C9A—C10A—C5A	173.0 (2)	C11B—C9B—C10B—C5B	172.2 (2)
C8A—C9A—C10A—C5A	−55.9 (2)	C8B—C9B—C10B—C5B	−55.4 (3)
C8A—C9A—C11A—C12A	44.2 (3)	C8B—C9B—C11B—C12B	41.1 (3)
C10A—C9A—C11A—C12A	178.6 (2)	C10B—C9B—C11B—C12B	176.0 (2)
C9A—C11A—C12A—O3A	149.4 (3)	C9B—C11B—C12B—O3B	150.1 (3)
C9A—C11A—C12A—C13A	−35.8 (3)	C9B—C11B—C12B—C13B	−34.8 (4)
O3A—C12A—C13A—C18A	−6.8 (4)	O3B—C12B—C13B—C18B	−4.9 (4)
C11A—C12A—C13A—C18A	178.6 (2)	C11B—C12B—C13B—C18B	−179.8 (2)
O3A—C12A—C13A—C14A	−142.7 (2)	O3B—C12B—C13B—C14B	−141.6 (3)
C11A—C12A—C13A—C14A	42.6 (3)	C11B—C12B—C13B—C14B	43.5 (3)
C12A—C13A—C14A—C27A	63.2 (3)	C12B—C13B—C14B—C15B	179.1 (2)
C18A—C13A—C14A—C27A	−71.5 (3)	C18B—C13B—C14B—C15B	43.7 (3)
C12A—C13A—C14A—C15A	−177.5 (2)	C12B—C13B—C14B—C27B	62.5 (3)
C18A—C13A—C14A—C15A	47.8 (3)	C18B—C13B—C14B—C27B	−72.9 (3)
C12A—C13A—C14A—C8A	−57.6 (3)	C12B—C13B—C14B—C8B	−59.1 (2)
C18A—C13A—C14A—C8A	167.7 (2)	C18B—C13B—C14B—C8B	165.55 (19)
C26A—C8A—C14A—C27A	−175.7 (2)	C7B—C8B—C14B—C15B	−52.9 (2)
C7A—C8A—C14A—C27A	65.4 (2)	C9B—C8B—C14B—C15B	−173.03 (18)
C9A—C8A—C14A—C27A	−53.1 (2)	C26B—C8B—C14B—C15B	65.2 (2)
C26A—C8A—C14A—C15A	63.0 (3)	C7B—C8B—C14B—C13B	−173.40 (18)
C7A—C8A—C14A—C15A	−55.9 (3)	C9B—C8B—C14B—C13B	66.5 (2)
C9A—C8A—C14A—C15A	−174.4 (2)	C26B—C8B—C14B—C13B	−55.3 (2)
C26A—C8A—C14A—C13A	−55.6 (2)	C7B—C8B—C14B—C27B	65.8 (2)
C7A—C8A—C14A—C13A	−174.52 (19)	C9B—C8B—C14B—C27B	−54.3 (2)
C9A—C8A—C14A—C13A	67.0 (2)	C26B—C8B—C14B—C27B	−176.1 (2)
C27A—C14A—C15A—C16A	72.8 (3)	C13B—C14B—C15B—C16B	−44.3 (3)
C13A—C14A—C15A—C16A	−47.0 (3)	C27B—C14B—C15B—C16B	74.5 (2)
C8A—C14A—C15A—C16A	−164.8 (2)	C8B—C14B—C15B—C16B	−164.07 (19)
C14A—C15A—C16A—C17A	55.9 (3)	C14B—C15B—C16B—C17B	55.5 (3)
C15A—C16A—C17A—C28A	62.5 (3)	C15B—C16B—C17B—C28B	60.9 (3)
C15A—C16A—C17A—C18A	−59.9 (3)	C15B—C16B—C17B—C22B	176.1 (2)
C15A—C16A—C17A—C22A	179.8 (3)	C15B—C16B—C17B—C18B	−60.4 (3)
C12A—C13A—C18A—C19A	−59.7 (3)	C28B—C17B—C18B—C13B	−65.3 (3)
C14A—C13A—C18A—C19A	73.7 (3)	C16B—C17B—C18B—C13B	56.3 (3)
C12A—C13A—C18A—C17A	172.2 (2)	C22B—C17B—C18B—C13B	179.6 (2)
C14A—C13A—C18A—C17A	−54.5 (3)	C28B—C17B—C18B—C19B	164.0 (2)
C28A—C17A—C18A—C19A	163.3 (2)	C16B—C17B—C18B—C19B	−74.3 (3)
C16A—C17A—C18A—C19A	−73.2 (3)	C22B—C17B—C18B—C19B	49.0 (3)
C22A—C17A—C18A—C19A	48.4 (4)	C12B—C13B—C18B—C17B	175.3 (2)
C28A—C17A—C18A—C13A	−66.4 (3)	C14B—C13B—C18B—C17B	−51.3 (3)
C16A—C17A—C18A—C13A	57.1 (3)	C12B—C13B—C18B—C19B	−57.1 (3)
C22A—C17A—C18A—C13A	178.7 (3)	C14B—C13B—C18B—C19B	76.3 (3)
C13A—C18A—C19A—C20A	176.6 (2)	C17B—C18B—C19B—C20B	−54.9 (3)
C17A—C18A—C19A—C20A	−56.9 (3)	C13B—C18B—C19B—C20B	178.2 (2)
C18A—C19A—C20A—C30A	−65.2 (4)	C18B—C19B—C20B—C21B	57.4 (4)
C18A—C19A—C20A—C29A	175.1 (3)	C18B—C19B—C20B—C29B	175.5 (3)
C18A—C19A—C20A—C21A	57.1 (4)	C18B—C19B—C20B—C30B	−64.7 (3)
C30A—C20A—C21A—C22A	68.0 (4)	C29B—C20B—C21B—C22B	−173.3 (3)
C29A—C20A—C21A—C22A	−172.8 (4)	C19B—C20B—C21B—C22B	−55.4 (4)
C19A—C20A—C21A—C22A	−54.7 (5)	C30B—C20B—C21B—C22B	66.7 (3)
C20A—C21A—C22A—C17A	53.3 (5)	C20B—C21B—C22B—C17B	53.4 (3)
C28A—C17A—C22A—C21A	−166.5 (4)	C28B—C17B—C22B—C21B	−168.0 (2)
C16A—C17A—C22A—C21A	72.0 (4)	C16B—C17B—C22B—C21B	72.7 (3)
C18A—C17A—C22A—C21A	−48.1 (4)	C18B—C17B—C22B—C21B	−49.2 (3)
C33A—O5A—C28A—O4A	−0.8 (6)	C33B—O5B—C28B—O4B	−0.6 (5)
C33A—O5A—C28A—C17A	176.3 (3)	C33B—O5B—C28B—C17B	178.1 (4)
C16A—C17A—C28A—O4A	−142.7 (4)	C16B—C17B—C28B—O4B	−144.8 (3)
C18A—C17A—C28A—O4A	−21.1 (5)	C22B—C17B—C28B—O4B	95.5 (4)
C22A—C17A—C28A—O4A	96.4 (4)	C18B—C17B—C28B—O4B	−24.3 (4)
C16A—C17A—C28A—O5A	40.4 (3)	C16B—C17B—C28B—O5B	36.7 (3)
C18A—C17A—C28A—O5A	161.9 (3)	C22B—C17B—C28B—O5B	−83.0 (3)
C22A—C17A—C28A—O5A	−80.5 (3)	C18B—C17B—C28B—O5B	157.1 (3)
C3A—O1A—C31A—O2A	−2.1 (3)	C3B—O1B—C31B—O2B	−7.9 (11)
C3A—O1A—C31A—C32A	176.4 (2)	C3B—O1B—C31B—C32B	177.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11B—H11D···O2A^i	0.97	2.45	3.336 (4)	152
C13A—H13A···O4A	0.98	2.50	3.155 (4)	124
C13B—H13B···O4B	0.98	2.53	3.187 (3)	124
C19A—H19A···O3A	0.97	2.42	3.051 (3)	122
C19B—H19D···O3B	0.97	2.40	3.038 (3)	123
C27B—H27E···O2A^ii	0.96	2.53	3.357 (4)	145

Symmetry codes: (i) x, y−1, z; (ii) x+1, y−1, z.

(II) Methyl 3β-acetoxy-12,19-dioxoolean-9(11),13 (18)-dien-28-oate

Crystal data

C33H46O6	F(000) = 584
Mr = 538.70	Dx = 1.183 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 7.9348 (8) Å	Cell parameters from 50 reflections
b = 15.8841 (10) Å	θ = 14.8–30.2°
c = 12.1480 (8) Å	µ = 0.64 mm^−1
β = 99.041 (7)°	T = 293 K
V = 1512.1 (2) Å^3	Prism, colourless
Z = 2	0.53 × 0.40 × 0.20 mm

Data collection

Kuma Diffraction KM-4 diffractometer	5157 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 70.2°, θmin = 3.7°
ω/2θ scans	h = −9→8
Absorption correction: ψ-scan (North et al., 1968)	k = −19→19
Tmin = 0.769, Tmax = 0.880	l = 0→14
5476 measured reflections	2 standard reflections every 100 reflections
5362 independent reflections	intensity decay: 1.7%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.1609P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.092	(Δ/σ)max = 0.007
S = 1.06	Δρmax = 0.16 e Å^−3
5362 reflections	Δρmin = −0.15 e Å^−3
362 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0059 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (15)

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	−0.21451 (17)	0.55406 (8)	0.66832 (10)	0.0593 (3)
O2	−0.3845 (2)	0.54561 (11)	0.79746 (15)	0.0908 (5)
O3	−0.09466 (16)	0.02786 (8)	0.79924 (15)	0.0776 (5)
O4	0.0972 (2)	−0.10255 (9)	0.70074 (10)	0.0794 (5)
O5	0.6296 (2)	−0.13339 (10)	0.81373 (15)	0.0829 (5)
O6	0.51164 (17)	−0.03240 (10)	0.70121 (10)	0.0673 (4)
C1	−0.1905 (2)	0.31773 (11)	0.67054 (15)	0.0535 (4)
H1A	−0.2631	0.2756	0.6291	0.064*
H1B	−0.1983	0.3109	0.7489	0.064*
C2	−0.2544 (2)	0.40533 (12)	0.63256 (16)	0.0587 (4)
H2A	−0.2489	0.4124	0.5539	0.070*
H2B	−0.3723	0.4118	0.6432	0.070*
C3	−0.1461 (2)	0.47068 (11)	0.69874 (14)	0.0505 (4)
H3A	−0.1508	0.4614	0.7780	0.061*
C4	0.0410 (2)	0.46894 (10)	0.68189 (14)	0.0483 (3)
C5	0.10629 (19)	0.37714 (9)	0.70842 (12)	0.0417 (3)
H5A	0.1051	0.3703	0.7885	0.050*
C6	0.2918 (2)	0.36398 (10)	0.69473 (15)	0.0515 (4)
H6A	0.2996	0.3561	0.6165	0.062*
H6B	0.3581	0.4134	0.7210	0.062*
C7	0.3637 (2)	0.28714 (10)	0.76072 (16)	0.0520 (4)
H7A	0.3716	0.2996	0.8395	0.062*
H7B	0.4787	0.2773	0.7458	0.062*
C8	0.25957 (18)	0.20516 (9)	0.73558 (12)	0.0402 (3)
C9	0.06651 (18)	0.22143 (9)	0.71069 (11)	0.0391 (3)
C10	−0.00415 (19)	0.30333 (9)	0.65292 (12)	0.0423 (3)
C11	−0.04033 (19)	0.16081 (10)	0.73254 (14)	0.0482 (3)
H11A	−0.1567	0.1713	0.7147	0.058*
C12	0.0117 (2)	0.07969 (9)	0.78201 (14)	0.0480 (3)
C13	0.19797 (18)	0.06521 (9)	0.81609 (11)	0.0377 (3)
C14	0.30427 (18)	0.14448 (9)	0.83941 (11)	0.0380 (3)
C15	0.49523 (19)	0.12273 (10)	0.85929 (14)	0.0466 (3)
H15A	0.5326	0.1134	0.7880	0.056*
H15B	0.5588	0.1702	0.8948	0.056*
C16	0.5356 (2)	0.04522 (11)	0.93160 (14)	0.0507 (4)
H16A	0.5059	0.0563	1.0047	0.061*
H16B	0.6574	0.0346	0.9410	0.061*
C17	0.4402 (2)	−0.03397 (10)	0.88293 (12)	0.0443 (3)
C18	0.25840 (18)	−0.01318 (9)	0.83012 (10)	0.0380 (3)
C19	0.1516 (2)	−0.08985 (9)	0.79642 (12)	0.0438 (3)
C20	0.1377 (2)	−0.15324 (10)	0.88818 (14)	0.0510 (4)
C21	0.3225 (3)	−0.17453 (12)	0.94023 (18)	0.0651 (5)
H21A	0.3200	−0.2107	1.0043	0.078*
H21B	0.3754	−0.2060	0.8863	0.078*
C22	0.4321 (2)	−0.09837 (12)	0.97692 (15)	0.0601 (4)
H22A	0.5470	−0.1172	1.0054	0.072*
H22B	0.3874	−0.0707	1.0374	0.072*
C23	0.1392 (3)	0.52821 (12)	0.7689 (2)	0.0713 (5)
H23A	0.2575	0.5289	0.7605	0.086*
H23B	0.1283	0.5088	0.8423	0.086*
H23C	0.0931	0.5840	0.7583	0.086*
C24	0.0627 (3)	0.49946 (12)	0.56554 (17)	0.0660 (5)
H24A	−0.0007	0.4635	0.5104	0.079*
H24B	0.1813	0.4979	0.5581	0.079*
H24C	0.0211	0.5561	0.5551	0.079*
C25	−0.0049 (3)	0.29330 (12)	0.52662 (14)	0.0621 (4)
H25A	0.1094	0.2987	0.5108	0.074*
H25B	−0.0756	0.3361	0.4872	0.074*
H25C	−0.0490	0.2388	0.5031	0.074*
C26	0.3089 (2)	0.16279 (12)	0.63033 (14)	0.0567 (4)
H26A	0.2570	0.1081	0.6208	0.068*
H26B	0.4307	0.1571	0.6388	0.068*
H26C	0.2697	0.1969	0.5662	0.068*
C27	0.2557 (2)	0.18357 (10)	0.94685 (13)	0.0495 (4)
H27A	0.1381	0.2005	0.9334	0.059*
H27B	0.3264	0.2318	0.9680	0.059*
H27C	0.2724	0.1427	1.0057	0.059*
C28	0.5381 (2)	−0.07352 (11)	0.79715 (15)	0.0524 (4)
C29	0.0445 (3)	−0.23155 (12)	0.8402 (2)	0.0741 (6)
H29A	0.0470	−0.2732	0.8977	0.089*
H29B	0.0993	−0.2534	0.7812	0.089*
H29C	−0.0718	−0.2176	0.8114	0.089*
C30	0.0427 (3)	−0.11365 (14)	0.97568 (16)	0.0657 (5)
H30A	−0.0742	−0.1040	0.9436	0.079*
H30B	0.0955	−0.0611	1.0002	0.079*
H30C	0.0471	−0.1511	1.0381	0.079*
C31	−0.3343 (2)	0.58312 (12)	0.72457 (16)	0.0591 (4)
C32	−0.3974 (4)	0.66756 (15)	0.6834 (2)	0.0868 (7)
H32A	−0.4647	0.6619	0.6109	0.104*
H32B	−0.3019	0.7038	0.6788	0.104*
H32C	−0.4661	0.6913	0.7339	0.104*
C33	0.6086 (3)	−0.0621 (2)	0.6175 (2)	0.0969 (9)
H33A	0.7276	−0.0634	0.6482	0.116*
H33B	0.5911	−0.0248	0.5545	0.116*
H33C	0.5713	−0.1177	0.5943	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0627 (7)	0.0506 (7)	0.0693 (7)	0.0175 (5)	0.0252 (6)	0.0143 (5)
O2	0.1008 (12)	0.0907 (11)	0.0935 (10)	0.0298 (10)	0.0541 (9)	0.0193 (9)
O3	0.0403 (7)	0.0520 (7)	0.1358 (13)	−0.0097 (5)	−0.0004 (7)	0.0288 (8)
O4	0.1217 (13)	0.0654 (8)	0.0466 (6)	−0.0336 (8)	−0.0010 (7)	−0.0070 (6)
O5	0.0647 (9)	0.0624 (8)	0.1261 (13)	0.0229 (7)	0.0288 (8)	−0.0061 (8)
O6	0.0606 (8)	0.0871 (9)	0.0575 (7)	0.0111 (7)	0.0200 (6)	−0.0093 (6)
C1	0.0356 (8)	0.0489 (9)	0.0734 (10)	0.0005 (6)	0.0007 (7)	0.0134 (8)
C2	0.0385 (9)	0.0567 (10)	0.0788 (11)	0.0065 (7)	0.0027 (8)	0.0156 (8)
C3	0.0501 (9)	0.0473 (8)	0.0568 (8)	0.0106 (7)	0.0166 (7)	0.0133 (7)
C4	0.0455 (9)	0.0412 (8)	0.0603 (9)	0.0018 (6)	0.0146 (7)	0.0045 (7)
C5	0.0384 (8)	0.0406 (7)	0.0477 (7)	−0.0011 (6)	0.0118 (6)	0.0042 (6)
C6	0.0386 (8)	0.0435 (8)	0.0757 (11)	−0.0047 (6)	0.0190 (7)	0.0052 (7)
C7	0.0330 (8)	0.0442 (8)	0.0785 (11)	−0.0047 (6)	0.0076 (7)	0.0048 (7)
C8	0.0351 (7)	0.0389 (7)	0.0473 (7)	−0.0008 (5)	0.0089 (6)	−0.0005 (5)
C9	0.0333 (7)	0.0414 (7)	0.0419 (7)	−0.0001 (5)	0.0031 (5)	0.0011 (5)
C10	0.0383 (8)	0.0419 (7)	0.0460 (7)	−0.0009 (6)	0.0040 (6)	0.0059 (6)
C11	0.0316 (7)	0.0447 (8)	0.0657 (9)	−0.0015 (6)	−0.0004 (6)	0.0069 (7)
C12	0.0360 (8)	0.0399 (7)	0.0665 (9)	−0.0034 (6)	0.0028 (7)	0.0055 (6)
C13	0.0336 (7)	0.0405 (7)	0.0384 (6)	−0.0003 (5)	0.0035 (5)	−0.0004 (5)
C14	0.0309 (7)	0.0383 (7)	0.0438 (7)	0.0002 (5)	0.0023 (5)	−0.0040 (5)
C15	0.0303 (7)	0.0455 (8)	0.0615 (8)	−0.0017 (6)	−0.0006 (6)	−0.0054 (7)
C16	0.0397 (8)	0.0528 (9)	0.0557 (8)	0.0064 (7)	−0.0050 (6)	−0.0050 (7)
C17	0.0392 (8)	0.0443 (7)	0.0480 (7)	0.0075 (6)	0.0028 (6)	−0.0001 (6)
C18	0.0383 (7)	0.0409 (7)	0.0344 (6)	0.0016 (6)	0.0047 (5)	−0.0003 (5)
C19	0.0479 (8)	0.0383 (7)	0.0454 (7)	0.0014 (6)	0.0077 (6)	−0.0032 (6)
C20	0.0545 (9)	0.0414 (8)	0.0570 (9)	0.0005 (7)	0.0090 (7)	0.0062 (6)
C21	0.0598 (11)	0.0513 (10)	0.0831 (12)	0.0098 (8)	0.0077 (9)	0.0216 (9)
C22	0.0523 (10)	0.0626 (10)	0.0615 (10)	0.0092 (8)	−0.0033 (8)	0.0171 (8)
C23	0.0644 (13)	0.0477 (9)	0.1008 (15)	−0.0004 (8)	0.0102 (11)	−0.0135 (10)
C24	0.0730 (12)	0.0517 (10)	0.0812 (12)	0.0084 (8)	0.0367 (10)	0.0200 (9)
C25	0.0809 (13)	0.0566 (10)	0.0462 (9)	0.0065 (9)	0.0023 (8)	0.0053 (7)
C26	0.0595 (10)	0.0626 (10)	0.0516 (8)	0.0103 (8)	0.0196 (7)	0.0015 (7)
C27	0.0526 (9)	0.0483 (8)	0.0472 (8)	0.0025 (7)	0.0068 (7)	−0.0065 (6)
C28	0.0400 (8)	0.0497 (9)	0.0684 (10)	0.0034 (7)	0.0110 (7)	−0.0092 (7)
C29	0.0787 (14)	0.0436 (9)	0.1010 (16)	−0.0081 (9)	0.0174 (12)	0.0052 (9)
C30	0.0632 (12)	0.0778 (13)	0.0594 (10)	−0.0017 (10)	0.0198 (8)	0.0075 (9)
C31	0.0585 (10)	0.0590 (10)	0.0624 (10)	0.0091 (8)	0.0173 (8)	−0.0012 (8)
C32	0.0933 (17)	0.0647 (13)	0.1067 (17)	0.0278 (12)	0.0289 (14)	0.0013 (12)
C33	0.0716 (14)	0.151 (3)	0.0755 (13)	0.0003 (16)	0.0337 (11)	−0.0333 (15)

Geometric parameters (Å, º)

O1—C31	1.337 (2)	C9—C11	1.337 (2)
O1—C3	1.4567 (19)	C9—C10	1.5413 (19)
O2—C31	1.187 (2)	C10—C25	1.542 (2)
O3—C12	1.2202 (19)	C11—C12	1.454 (2)
O4—C19	1.1918 (19)	C12—C13	1.489 (2)
O5—C28	1.194 (2)	C13—C18	1.336 (2)
O6—C28	1.324 (2)	C13—C14	1.5172 (19)
O6—C33	1.447 (2)	C14—C15	1.536 (2)
C1—C2	1.527 (2)	C14—C27	1.548 (2)
C1—C10	1.544 (2)	C15—C16	1.517 (2)
C2—C3	1.498 (3)	C16—C17	1.538 (2)
C3—C4	1.530 (2)	C17—C18	1.520 (2)
C4—C24	1.529 (2)	C17—C28	1.529 (2)
C4—C23	1.534 (3)	C17—C22	1.542 (2)
C4—C5	1.564 (2)	C18—C19	1.503 (2)
C5—C6	1.522 (2)	C19—C20	1.519 (2)
C5—C10	1.553 (2)	C20—C29	1.516 (3)
C6—C7	1.521 (2)	C20—C30	1.531 (3)
C7—C8	1.547 (2)	C20—C21	1.541 (3)
C8—C9	1.536 (2)	C21—C22	1.515 (3)
C8—C26	1.549 (2)	C31—C32	1.490 (3)
C8—C14	1.5828 (19)
C31—O1—C3	116.77 (13)	C18—C13—C12	120.02 (13)
C28—O6—C33	115.45 (18)	C18—C13—C14	124.89 (13)
C2—C1—C10	111.88 (13)	C12—C13—C14	114.98 (12)
C3—C2—C1	109.51 (14)	C13—C14—C15	110.40 (11)
O1—C3—C2	109.54 (14)	C13—C14—C27	106.59 (12)
O1—C3—C4	108.23 (13)	C15—C14—C27	109.15 (12)
C2—C3—C4	113.71 (14)	C13—C14—C8	107.95 (11)
C24—C4—C3	111.75 (15)	C15—C14—C8	110.75 (11)
C24—C4—C23	108.87 (16)	C27—C14—C8	111.93 (12)
C3—C4—C23	107.17 (14)	C16—C15—C14	112.75 (13)
C24—C4—C5	113.83 (13)	C15—C16—C17	113.27 (12)
C3—C4—C5	106.64 (12)	C18—C17—C28	110.60 (12)
C23—C4—C5	108.32 (14)	C18—C17—C16	111.20 (12)
C6—C5—C10	109.79 (12)	C28—C17—C16	109.02 (13)
C6—C5—C4	113.61 (12)	C18—C17—C22	108.06 (13)
C10—C5—C4	117.92 (12)	C28—C17—C22	108.46 (13)
C7—C6—C5	109.99 (12)	C16—C17—C22	109.46 (13)
C6—C7—C8	115.26 (13)	C13—C18—C19	123.01 (13)
C9—C8—C7	112.50 (12)	C13—C18—C17	123.67 (13)
C9—C8—C26	106.52 (12)	C19—C18—C17	113.32 (12)
C7—C8—C26	109.41 (13)	O4—C19—C18	120.33 (14)
C9—C8—C14	110.55 (11)	O4—C19—C20	123.14 (15)
C7—C8—C14	108.02 (12)	C18—C19—C20	116.10 (12)
C26—C8—C14	109.83 (12)	C29—C20—C19	110.43 (15)
C11—C9—C8	118.93 (13)	C29—C20—C30	109.89 (16)
C11—C9—C10	120.11 (13)	C19—C20—C30	109.72 (13)
C8—C9—C10	120.79 (12)	C29—C20—C21	110.67 (15)
C9—C10—C25	108.07 (12)	C19—C20—C21	105.82 (14)
C9—C10—C1	110.47 (12)	C30—C20—C21	110.24 (15)
C25—C10—C1	107.41 (13)	C22—C21—C20	114.25 (14)
C9—C10—C5	107.42 (11)	C21—C22—C17	113.61 (14)
C25—C10—C5	115.07 (13)	O5—C28—O6	123.35 (17)
C1—C10—C5	108.38 (12)	O5—C28—C17	124.94 (18)
C9—C11—C12	124.94 (14)	O6—C28—C17	111.71 (13)
O3—C12—C11	120.65 (14)	O2—C31—O1	123.84 (17)
O3—C12—C13	122.08 (14)	O2—C31—C32	124.62 (18)
C11—C12—C13	117.17 (13)	O1—C31—C32	111.53 (17)
C10—C1—C2—C3	−60.68 (19)	C18—C13—C14—C8	132.20 (13)
C31—O1—C3—C2	87.89 (18)	C12—C13—C14—C8	−51.73 (15)
C31—O1—C3—C4	−147.63 (16)	C9—C8—C14—C13	54.82 (14)
C1—C2—C3—O1	−175.88 (13)	C7—C8—C14—C13	178.30 (12)
C1—C2—C3—C4	62.89 (18)	C26—C8—C14—C13	−62.44 (15)
O1—C3—C4—C24	−51.67 (19)	C9—C8—C14—C15	175.78 (11)
C2—C3—C4—C24	70.28 (18)	C7—C8—C14—C15	−60.74 (14)
O1—C3—C4—C23	67.52 (17)	C26—C8—C14—C15	58.52 (15)
C2—C3—C4—C23	−170.52 (15)	C9—C8—C14—C27	−62.17 (15)
O1—C3—C4—C5	−176.66 (13)	C7—C8—C14—C27	61.31 (15)
C2—C3—C4—C5	−54.70 (17)	C26—C8—C14—C27	−179.44 (13)
C24—C4—C5—C6	55.8 (2)	C13—C14—C15—C16	−42.27 (16)
C3—C4—C5—C6	179.52 (14)	C27—C14—C15—C16	74.58 (15)
C23—C4—C5—C6	−65.42 (18)	C8—C14—C15—C16	−161.77 (12)
C24—C4—C5—C10	−74.71 (18)	C14—C15—C16—C17	58.47 (17)
C3—C4—C5—C10	48.99 (17)	C15—C16—C17—C18	−39.23 (18)
C23—C4—C5—C10	164.05 (14)	C15—C16—C17—C28	82.97 (16)
C10—C5—C6—C7	−66.45 (17)	C15—C16—C17—C22	−158.55 (14)
C4—C5—C6—C7	159.09 (13)	C12—C13—C18—C19	9.7 (2)
C5—C6—C7—C8	53.56 (19)	C14—C13—C18—C19	−174.43 (12)
C6—C7—C8—C9	−35.29 (18)	C12—C13—C18—C17	−169.41 (13)
C6—C7—C8—C26	82.89 (17)	C14—C13—C18—C17	6.5 (2)
C6—C7—C8—C14	−157.58 (13)	C28—C17—C18—C13	−113.58 (15)
C7—C8—C9—C11	−152.60 (15)	C16—C17—C18—C13	7.69 (19)
C26—C8—C9—C11	87.53 (17)	C22—C17—C18—C13	127.85 (15)
C14—C8—C9—C11	−31.75 (19)	C28—C17—C18—C19	67.25 (16)
C7—C8—C9—C10	32.20 (18)	C16—C17—C18—C19	−171.47 (12)
C26—C8—C9—C10	−87.66 (16)	C22—C17—C18—C19	−51.32 (16)
C14—C8—C9—C10	153.06 (12)	C13—C18—C19—O4	64.7 (2)
C11—C9—C10—C25	−94.47 (18)	C17—C18—C19—O4	−116.15 (19)
C8—C9—C10—C25	80.66 (16)	C13—C18—C19—C20	−122.63 (15)
C11—C9—C10—C1	22.8 (2)	C17—C18—C19—C20	56.54 (17)
C8—C9—C10—C1	−162.09 (13)	O4—C19—C20—C29	−0.9 (3)
C11—C9—C10—C5	140.80 (15)	C18—C19—C20—C29	−173.34 (15)
C8—C9—C10—C5	−44.06 (16)	O4—C19—C20—C30	−122.2 (2)
C2—C1—C10—C9	169.92 (13)	C18—C19—C20—C30	65.38 (18)
C2—C1—C10—C25	−72.43 (18)	O4—C19—C20—C21	118.9 (2)
C2—C1—C10—C5	52.47 (18)	C18—C19—C20—C21	−53.54 (18)
C6—C5—C10—C9	59.43 (15)	C29—C20—C21—C22	172.50 (17)
C4—C5—C10—C9	−168.31 (12)	C19—C20—C21—C22	52.9 (2)
C6—C5—C10—C25	−60.95 (17)	C30—C20—C21—C22	−65.7 (2)
C4—C5—C10—C25	71.31 (17)	C20—C21—C22—C17	−56.0 (2)
C6—C5—C10—C1	178.81 (12)	C18—C17—C22—C21	51.92 (18)
C4—C5—C10—C1	−48.93 (16)	C28—C17—C22—C21	−68.01 (18)
C8—C9—C11—C12	1.9 (3)	C16—C17—C22—C21	173.16 (14)
C10—C9—C11—C12	177.13 (14)	C33—O6—C28—O5	−3.1 (3)
C9—C11—C12—O3	179.93 (19)	C33—O6—C28—C17	175.98 (17)
C9—C11—C12—C13	3.3 (3)	C18—C17—C28—O5	−136.23 (18)
O3—C12—C13—C18	23.6 (3)	C16—C17—C28—O5	101.21 (19)
C11—C12—C13—C18	−159.91 (14)	C22—C17—C28—O5	−17.9 (2)
O3—C12—C13—C14	−152.73 (17)	C18—C17—C28—O6	44.73 (18)
C11—C12—C13—C14	23.8 (2)	C16—C17—C28—O6	−77.83 (16)
C18—C13—C14—C15	11.01 (18)	C22—C17—C28—O6	163.06 (14)
C12—C13—C14—C15	−172.91 (13)	C3—O1—C31—O2	1.1 (3)
C18—C13—C14—C27	−107.40 (15)	C3—O1—C31—C32	−178.25 (19)
C12—C13—C14—C27	68.67 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O6	0.97	2.54	3.139 (2)	120
C25—H25B···O4^i	0.96	2.46	3.204 (2)	134
C33—H33A···O3^ii	0.96	2.58	3.290 (3)	131

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) x+1, y, z.