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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100005801/jz1393sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005801/jz1393Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005801/jz1393IIsup3.hkl
Contains datablock II

CCDC references: 150337; 150338

Comment top

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 [Uäq: 0,177 (3), 0,264 (6), 0,1455 (13) und 0,217 (2) Å2] und die Atome C33A und C33B [Uäq: 0,176 (3) und 0,148 (2) Å2]. 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 C31O2 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 C12O3 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 C12O3 und C19O4. Im zentralen Teil des Moleküls von (II) sind drei konjugierte Fragmente zu berücksichtigen und zwar das gänzlich planare C9C11—C12O3 [r.m.s. = 0.0003 Å], das annähernd flache O3C12—C13C18 [r.m.s. = 0.0733 Å] und das stark gefaltete System C13C18—C19O4 [r.m.s. = 0.1813 Å]. Demzufolge beteiligt sich die C19O4 Carbonylgruppe nicht an der Konjugation des zuletzt erwähnten Systems, die C12O3 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 C19O4 Gruppe [1,1918 (19) Å] ist dieser um etwa 11σ kürzer als in der C12O3 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 C28O4 in (I) eine Mittellage zwischen synperiplanarer und synklinaler, die Carbonylgruppe C28O5 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 C31O2 von (I) (beide Moleküle), C12O3 und C19O4 von (II) beteiligen (Tabelle 2 und 3).

Experimental top

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

Refinement top

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; Uiso(H) = 1,2Uäq(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 top

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 top
[Figure 1] Fig. 1. Abb. 1. Molekülstruktur von (I), (a) Molekül A, (b) Molekül B; Wahrscheinlichkeitsniveau der Ellipsoide 30%.
[Figure 2] Fig. 2. Abb. 2. Molekülstruktur von (II); Wahrscheinlichkeitsniveau der Ellipsoide 50%.
(I) Methyl 3β-acetoxy-12-oxo-18β-olean-28-oate top
Crystal data top
C33H52O5Dx = 1.121 Mg m3
Mr = 528.75Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 46 reflections
a = 7.0662 (16) Åθ = 12.6–26.3°
b = 22.083 (3) ŵ = 0.58 mm1
c = 40.141 (5) ÅT = 293 K
V = 6263.7 (18) Å3Needle, colourless
Z = 80.50 × 0.14 × 0.09 mm
F(000) = 2320
Data collection top
Kuma Diffraction KM-4
diffractometer
Rint = 0.017
Radiation source: fine-focus sealed tubeθmax = 65.1°, θmin = 2.2°
Graphite monochromatorh = 77
ω/2θ scansk = 025
10738 measured reflectionsl = 047
10265 independent reflections2 standard reflections every 100 reflections
7013 reflections with I > 2σ(I) intensity decay: 11.3%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0813P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.130(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.20 e Å3
10265 reflectionsΔρmin = 0.18 e Å3
704 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00025 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.0 (2)
Crystal data top
C33H52O5V = 6263.7 (18) Å3
Mr = 528.75Z = 8
Orthorhombic, P212121Cu Kα radiation
a = 7.0662 (16) ŵ = 0.58 mm1
b = 22.083 (3) ÅT = 293 K
c = 40.141 (5) Å0.50 × 0.14 × 0.09 mm
Data collection top
Kuma Diffraction KM-4
diffractometer
Rint = 0.017
10738 measured reflections2 standard reflections every 100 reflections
10265 independent reflections intensity decay: 11.3%
7013 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130Δρmax = 0.20 e Å3
S = 1.08Δρmin = 0.18 e Å3
10265 reflectionsAbsolute structure: Flack (1983)
704 parametersAbsolute structure parameter: 0.0 (2)
0 restraints
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
xyzUiso*/Ueq
O1A0.4257 (2)0.25620 (7)0.05032 (4)0.0597 (4)
O2a0.3864 (3)0.28635 (10)0.10255 (5)0.0936 (6)
O3A0.1264 (3)0.10117 (9)0.12945 (5)0.0889 (6)
O4A0.2997 (5)0.25256 (14)0.05773 (8)0.1321 (10)
O5A0.5927 (5)0.27344 (12)0.04357 (7)0.1301 (10)
C1A0.2323 (3)0.10562 (11)0.07847 (6)0.0621 (6)
H1A0.10330.09160.08130.075*
H1B0.29310.10470.10010.075*
C2A0.2287 (3)0.17072 (11)0.06593 (6)0.0631 (6)
H2A0.15990.17270.04510.076*
H2B0.16410.19620.08200.076*
C3A0.4284 (3)0.19339 (11)0.06084 (6)0.0549 (5)
H3A0.49490.19110.08220.066*
C4A0.5409 (3)0.15687 (10)0.03526 (5)0.0522 (5)
C5A0.5349 (3)0.09001 (10)0.04694 (5)0.0511 (5)
H5A0.60080.09030.06840.061*
C6A0.6486 (3)0.04619 (11)0.02571 (6)0.0609 (6)
H6A0.57880.03710.00550.073*
H6B0.76720.06510.01940.073*
C7A0.6892 (3)0.01221 (11)0.04423 (7)0.0643 (6)
H7A0.77170.00330.06290.077*
H7B0.75680.03940.02950.077*
C8A0.5109 (3)0.04485 (10)0.05735 (6)0.0557 (6)
C9A0.3806 (3)0.00212 (10)0.07449 (6)0.0534 (5)
H9A0.45150.01530.09420.064*
C10A0.3368 (3)0.06210 (11)0.05500 (6)0.0538 (5)
C11A0.2026 (3)0.02887 (11)0.08859 (7)0.0661 (7)
H11A0.14070.00070.10360.079*
H11B0.11630.03640.07030.079*
C12A0.2329 (3)0.08725 (11)0.10683 (7)0.0636 (6)
C13A0.3850 (4)0.12913 (11)0.09435 (6)0.0608 (6)
H13A0.33610.14360.07290.073*
C14A0.5676 (3)0.09381 (11)0.08484 (6)0.0580 (6)
C15A0.7142 (4)0.13912 (12)0.07077 (7)0.0721 (7)
H15A0.67600.15060.04840.087*
H15B0.83570.11890.06910.087*
C16A0.7382 (4)0.19603 (13)0.09144 (9)0.0846 (9)
H16A0.79110.18530.11290.102*
H16B0.82710.22280.08040.102*
C17A0.5495 (4)0.22991 (12)0.09680 (8)0.0802 (8)
C18A0.4098 (4)0.18741 (11)0.11504 (7)0.0700 (7)
H18A0.28690.20800.11470.084*
C19A0.4607 (4)0.17893 (13)0.15148 (7)0.0811 (8)
H19A0.36680.15290.16170.097*
H19B0.58180.15840.15280.097*
C20A0.4725 (6)0.23781 (15)0.17136 (8)0.0984 (11)
C21A0.6193 (6)0.27842 (17)0.15384 (10)0.1151 (13)
H21A0.74320.25990.15600.138*
H21B0.62350.31730.16510.138*
C22A0.5790 (6)0.28859 (14)0.11809 (10)0.1107 (13)
H22A0.46600.31330.11630.133*
H22B0.68290.31150.10860.133*
C23A0.7467 (3)0.17965 (12)0.03700 (7)0.0652 (6)
H23A0.74880.22280.03410.078*
H23B0.81970.16090.01970.078*
H23C0.79980.16950.05830.078*
C24A0.4685 (4)0.16767 (12)0.00013 (6)0.0657 (6)
H24A0.33320.16380.00050.079*
H24B0.52340.13830.01490.079*
H24C0.50330.20770.00720.079*
C25A0.2121 (4)0.05261 (12)0.02414 (7)0.0697 (7)
H25A0.11720.02270.02890.084*
H25B0.28900.03900.00590.084*
H25C0.15200.09010.01830.084*
C26A0.4139 (4)0.07485 (13)0.02723 (6)0.0738 (7)
H26A0.41910.04800.00850.089*
H26B0.28420.08330.03260.089*
H26C0.47790.11190.02190.089*
C27A0.6512 (4)0.06277 (12)0.11610 (7)0.0683 (7)
H27A0.73290.09060.12750.082*
H27B0.55020.05070.13070.082*
H27C0.72220.02770.10950.082*
C28A0.4645 (7)0.25178 (14)0.06431 (9)0.0943 (10)
C29A0.5409 (8)0.2239 (2)0.20643 (9)0.1384 (18)
H29A0.44730.20010.21780.166*
H29B0.65740.20160.20530.166*
H29C0.56120.26110.21830.166*
C30A0.2818 (7)0.26909 (17)0.17396 (10)0.1212 (14)
H30A0.29410.30490.18730.145*
H30B0.23860.28000.15210.145*
H30C0.19210.24210.18410.145*
C31A0.4065 (4)0.29817 (12)0.07359 (7)0.0661 (7)
C32A0.4179 (5)0.36040 (12)0.06009 (8)0.0867 (8)
H32A0.30320.36970.04830.104*
H32B0.52340.36330.04510.104*
H32C0.43440.38860.07810.104*
C33A0.5246 (10)0.2989 (2)0.01258 (12)0.176 (3)
H33A0.41990.32540.01700.211*
H33B0.62450.32140.00210.211*
H33C0.48440.26690.00190.211*
O1B1.0702 (5)0.96338 (11)0.20038 (7)0.1455 (13)
O2B1.3473 (8)0.9789 (2)0.17819 (14)0.217 (2)
O3B0.8790 (4)0.63328 (9)0.08424 (4)0.0903 (6)
O4B0.5450 (3)0.49440 (11)0.15137 (6)0.0981 (7)
O5B0.6756 (3)0.45695 (14)0.19632 (6)0.1219 (10)
C1B0.9359 (5)0.83188 (12)0.14611 (7)0.0833 (9)
H1C0.85210.83000.12700.100*
H1D1.06170.82050.13870.100*
C2B0.9410 (6)0.89676 (15)0.15921 (8)0.1056 (12)
H2C0.81390.90960.16490.127*
H2D0.98850.92350.14200.127*
C3B1.0661 (6)0.90107 (15)0.18949 (9)0.1022 (12)
H3B1.19470.88900.18320.123*
C4B1.0022 (5)0.86193 (14)0.21843 (7)0.0832 (8)
C5B0.9868 (4)0.79626 (12)0.20480 (6)0.0688 (7)
H5B1.11620.78630.19800.083*
C6B0.9407 (4)0.74945 (14)0.23099 (6)0.0761 (8)
H6C1.01310.75790.25100.091*
H6D0.80740.75190.23660.091*
C7B0.9860 (4)0.68606 (13)0.21889 (6)0.0702 (7)
H7C1.12220.68230.21660.084*
H7D0.94580.65730.23570.084*
C8B0.8935 (3)0.66890 (11)0.18572 (5)0.0557 (6)
C9B0.9194 (3)0.72118 (11)0.16055 (6)0.0585 (6)
H9B1.05630.72290.15680.070*
C10B0.8674 (4)0.78592 (12)0.17275 (6)0.0659 (6)
C11B0.8373 (5)0.70527 (12)0.12670 (6)0.0743 (8)
H11C0.88910.73340.11050.089*
H11D0.70180.71220.12760.089*
C12B0.8692 (4)0.64224 (12)0.11391 (6)0.0637 (6)
C13B0.8714 (3)0.59156 (11)0.13928 (5)0.0562 (6)
H13B0.74070.59020.14740.067*
C14B0.9870 (3)0.61032 (11)0.17036 (5)0.0543 (6)
C15B0.9898 (3)0.55760 (12)0.19551 (6)0.0647 (6)
H15C0.86900.55650.20700.078*
H15D1.08670.56560.21200.078*
C16B1.0263 (3)0.49614 (12)0.18039 (6)0.0636 (6)
H16C1.15380.49520.17140.076*
H16D1.01830.46560.19770.076*
C17B0.8864 (4)0.48045 (11)0.15269 (7)0.0643 (6)
C18B0.9039 (4)0.52792 (11)0.12487 (6)0.0630 (6)
H18B0.79850.52040.10960.076*
C19B1.0857 (4)0.51840 (12)0.10450 (6)0.0738 (7)
H19C1.19390.52660.11870.089*
H19D1.08790.54740.08640.089*
C20B1.1057 (6)0.45480 (14)0.09005 (8)0.0910 (9)
C21B1.0982 (5)0.40955 (13)0.11831 (8)0.0905 (9)
H21C1.10320.36890.10920.109*
H21D1.20840.41500.13240.109*
C22B0.9190 (5)0.41604 (13)0.13955 (8)0.0849 (8)
H22C0.81050.40400.12630.102*
H22D0.92750.38850.15830.102*
C23B1.1585 (6)0.86436 (18)0.24507 (10)0.1200 (13)
H23D1.18650.90580.25030.144*
H23E1.11620.84390.26480.144*
H23F1.27040.84490.23670.144*
C24B0.8185 (6)0.88593 (15)0.23389 (8)0.0976 (11)
H24D0.72610.89200.21670.117*
H24E0.77120.85710.24970.117*
H24F0.84310.92370.24490.117*
C25B0.6539 (4)0.79569 (14)0.17764 (8)0.0847 (8)
H25D0.62640.83820.17700.102*
H25E0.58580.77550.16020.102*
H25F0.61620.77940.19880.102*
C26B0.6806 (4)0.65751 (13)0.19327 (7)0.0748 (7)
H26D0.63740.68620.20950.090*
H26E0.60840.66210.17320.090*
H26F0.66460.61720.20180.090*
C27B1.1964 (3)0.62222 (12)0.16039 (6)0.0638 (6)
H27D1.26320.58440.15920.077*
H27E1.20030.64180.13900.077*
H27F1.25490.64780.17680.077*
C28B0.6841 (4)0.47899 (13)0.16603 (8)0.0745 (8)
C29B1.2974 (7)0.45016 (19)0.07301 (10)0.1288 (16)
H29D1.31340.41010.06420.155*
H29E1.30410.47910.05520.155*
H29F1.39580.45830.08890.155*
C30B0.9489 (8)0.44198 (17)0.06432 (9)0.1265 (15)
H30D0.96460.40190.05550.152*
H30E0.82740.44510.07490.152*
H30F0.95700.47090.04650.152*
C31B1.2227 (13)0.9967 (3)0.19477 (13)0.177 (3)
C32B1.2024 (15)1.0577 (2)0.20881 (12)0.264 (6)
H32D1.11641.08080.19530.317*
H32E1.15391.05490.23110.317*
H32F1.32361.07730.20920.317*
C33B0.4868 (5)0.4520 (2)0.21064 (12)0.148 (2)
H33D0.40500.43140.19530.177*
H33E0.49320.42960.23110.177*
H33F0.43780.49180.21500.177*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0501 (9)0.0643 (10)0.0648 (9)0.0060 (7)0.0004 (7)0.0012 (8)
O2A0.0986 (16)0.1079 (15)0.0744 (13)0.0301 (13)0.0023 (12)0.0154 (11)
O3A0.0547 (11)0.1003 (13)0.1117 (14)0.0184 (10)0.0265 (11)0.0398 (12)
O4A0.117 (2)0.143 (2)0.137 (2)0.0057 (19)0.0102 (19)0.0380 (18)
O5A0.137 (2)0.1236 (19)0.129 (2)0.0030 (18)0.0503 (19)0.0352 (17)
C1A0.0342 (12)0.0722 (15)0.0800 (16)0.0129 (11)0.0142 (11)0.0147 (13)
C2A0.0370 (13)0.0738 (16)0.0784 (16)0.0141 (11)0.0121 (11)0.0097 (13)
C3A0.0388 (12)0.0664 (14)0.0597 (13)0.0082 (10)0.0028 (10)0.0058 (11)
C4A0.0326 (11)0.0668 (14)0.0572 (12)0.0027 (9)0.0035 (9)0.0075 (11)
C5A0.0279 (11)0.0666 (14)0.0589 (12)0.0058 (9)0.0033 (9)0.0055 (11)
C6A0.0382 (12)0.0686 (15)0.0760 (16)0.0053 (10)0.0157 (11)0.0062 (12)
C7A0.0394 (13)0.0680 (15)0.0856 (17)0.0121 (11)0.0198 (11)0.0062 (13)
C8A0.0394 (12)0.0600 (14)0.0677 (14)0.0043 (10)0.0086 (11)0.0045 (11)
C9A0.0282 (11)0.0647 (14)0.0674 (14)0.0057 (10)0.0066 (10)0.0092 (11)
C10A0.0299 (11)0.0657 (14)0.0658 (13)0.0049 (10)0.0052 (10)0.0116 (11)
C11A0.0349 (12)0.0725 (15)0.0910 (18)0.0068 (10)0.0138 (12)0.0166 (14)
C12A0.0384 (13)0.0742 (16)0.0781 (17)0.0016 (11)0.0044 (12)0.0118 (13)
C13A0.0489 (14)0.0612 (14)0.0723 (14)0.0050 (11)0.0062 (11)0.0074 (12)
C14A0.0359 (12)0.0634 (14)0.0747 (15)0.0101 (10)0.0052 (10)0.0055 (12)
C15A0.0496 (15)0.0681 (16)0.0986 (19)0.0117 (12)0.0170 (13)0.0055 (14)
C16A0.0672 (18)0.0720 (17)0.115 (2)0.0252 (14)0.0206 (17)0.0088 (16)
C17A0.083 (2)0.0625 (16)0.095 (2)0.0167 (14)0.0212 (17)0.0101 (15)
C18A0.0642 (16)0.0632 (15)0.0825 (17)0.0107 (13)0.0125 (14)0.0120 (13)
C19A0.083 (2)0.0771 (18)0.0831 (18)0.0253 (15)0.0107 (16)0.0130 (15)
C20A0.115 (3)0.093 (2)0.088 (2)0.042 (2)0.0201 (19)0.0302 (18)
C21A0.133 (3)0.099 (2)0.113 (3)0.057 (2)0.032 (2)0.037 (2)
C22A0.133 (3)0.0743 (19)0.125 (3)0.042 (2)0.044 (3)0.0238 (19)
C23A0.0353 (12)0.0735 (15)0.0869 (17)0.0009 (11)0.0056 (12)0.0073 (14)
C24A0.0556 (15)0.0772 (16)0.0645 (14)0.0057 (12)0.0054 (12)0.0087 (12)
C25A0.0398 (13)0.0808 (17)0.0883 (19)0.0024 (12)0.0069 (12)0.0206 (15)
C26A0.0710 (17)0.0796 (17)0.0708 (16)0.0046 (14)0.0036 (14)0.0011 (13)
C27A0.0458 (14)0.0744 (16)0.0846 (17)0.0132 (12)0.0063 (13)0.0085 (14)
C28A0.111 (3)0.0692 (18)0.102 (2)0.0039 (19)0.030 (2)0.0028 (17)
C29A0.174 (5)0.144 (3)0.097 (3)0.059 (3)0.011 (3)0.039 (3)
C30A0.136 (4)0.097 (2)0.131 (3)0.021 (2)0.047 (3)0.035 (2)
C31A0.0447 (14)0.0794 (17)0.0742 (17)0.0138 (12)0.0075 (12)0.0082 (15)
C32A0.0756 (19)0.0739 (18)0.111 (2)0.0113 (15)0.0145 (18)0.0104 (17)
C33A0.214 (7)0.174 (5)0.138 (4)0.038 (4)0.062 (4)0.071 (4)
O1B0.208 (3)0.0907 (16)0.138 (2)0.059 (2)0.077 (2)0.0451 (15)
O2B0.222 (5)0.183 (4)0.245 (5)0.125 (4)0.059 (4)0.015 (4)
O3B0.1343 (19)0.0833 (12)0.0534 (10)0.0002 (12)0.0190 (11)0.0017 (9)
O4B0.0534 (12)0.1265 (17)0.1146 (16)0.0142 (11)0.0160 (12)0.0260 (14)
O5B0.0444 (11)0.190 (3)0.1316 (19)0.0092 (13)0.0064 (12)0.0880 (19)
C1B0.111 (2)0.0700 (17)0.0686 (16)0.0094 (16)0.0210 (16)0.0042 (14)
C2B0.153 (4)0.077 (2)0.087 (2)0.014 (2)0.043 (2)0.0032 (17)
C3B0.122 (3)0.087 (2)0.097 (2)0.033 (2)0.045 (2)0.0322 (18)
C4B0.082 (2)0.092 (2)0.0756 (17)0.0147 (16)0.0221 (16)0.0261 (16)
C5B0.0556 (15)0.0864 (18)0.0644 (14)0.0110 (13)0.0122 (12)0.0168 (13)
C6B0.0701 (18)0.104 (2)0.0542 (13)0.0061 (16)0.0054 (12)0.0122 (14)
C7B0.0651 (17)0.0930 (18)0.0524 (13)0.0092 (14)0.0009 (12)0.0021 (13)
C8B0.0390 (12)0.0743 (15)0.0539 (12)0.0102 (10)0.0016 (10)0.0018 (11)
C9B0.0525 (13)0.0707 (15)0.0523 (12)0.0088 (11)0.0019 (10)0.0009 (11)
C10B0.0612 (15)0.0751 (16)0.0613 (14)0.0073 (12)0.0080 (12)0.0031 (12)
C11B0.093 (2)0.0700 (16)0.0604 (15)0.0053 (14)0.0125 (14)0.0062 (13)
C12B0.0638 (16)0.0725 (16)0.0549 (14)0.0098 (13)0.0156 (12)0.0040 (12)
C13B0.0465 (13)0.0673 (14)0.0548 (12)0.0134 (10)0.0086 (10)0.0058 (11)
C14B0.0384 (12)0.0707 (15)0.0538 (12)0.0104 (10)0.0027 (10)0.0038 (11)
C15B0.0488 (13)0.0893 (18)0.0561 (13)0.0050 (13)0.0043 (11)0.0122 (13)
C16B0.0470 (13)0.0759 (16)0.0681 (14)0.0080 (11)0.0040 (11)0.0176 (13)
C17B0.0493 (14)0.0690 (15)0.0748 (15)0.0144 (11)0.0054 (12)0.0095 (13)
C18B0.0569 (15)0.0693 (15)0.0627 (14)0.0140 (12)0.0094 (12)0.0084 (12)
C19B0.0850 (19)0.0716 (16)0.0646 (15)0.0106 (14)0.0024 (14)0.0058 (13)
C20B0.122 (3)0.0780 (19)0.0726 (18)0.0064 (18)0.0084 (19)0.0082 (15)
C21B0.104 (2)0.0674 (17)0.100 (2)0.0031 (17)0.0026 (19)0.0027 (16)
C22B0.082 (2)0.0723 (18)0.101 (2)0.0164 (15)0.0075 (17)0.0126 (16)
C23B0.113 (3)0.128 (3)0.120 (3)0.024 (2)0.004 (2)0.052 (2)
C24B0.113 (3)0.092 (2)0.088 (2)0.0030 (19)0.0430 (19)0.0227 (18)
C25B0.0649 (18)0.089 (2)0.100 (2)0.0082 (14)0.0044 (16)0.0065 (17)
C26B0.0444 (14)0.0880 (19)0.0920 (19)0.0102 (12)0.0111 (13)0.0032 (15)
C27B0.0422 (13)0.0803 (16)0.0690 (15)0.0136 (11)0.0028 (11)0.0070 (13)
C28B0.0537 (17)0.0815 (18)0.088 (2)0.0179 (13)0.0095 (14)0.0208 (16)
C29B0.162 (4)0.109 (3)0.115 (3)0.014 (3)0.051 (3)0.012 (2)
C30B0.193 (5)0.094 (2)0.093 (2)0.013 (3)0.030 (3)0.019 (2)
C31B0.284 (9)0.137 (4)0.109 (3)0.119 (6)0.061 (4)0.028 (3)
C32B0.542 (16)0.124 (4)0.126 (3)0.168 (7)0.090 (6)0.046 (3)
C33B0.0498 (19)0.228 (5)0.165 (4)0.006 (3)0.020 (2)0.098 (4)
Geometric parameters (Å, º) top
O1A—C31A1.323 (3)O1B—C31B1.324 (7)
O1A—C3A1.450 (3)O1B—C3B1.444 (4)
O2A—C31A1.200 (3)O2B—C31B1.171 (8)
O3A—C12A1.218 (3)O3B—C12B1.209 (3)
O4A—C28A1.194 (5)O4B—C28B1.195 (3)
O5A—C28A1.320 (4)O5B—C28B1.311 (3)
O5A—C33A1.448 (5)O5B—C33B1.457 (4)
C1A—C2A1.524 (4)C1B—C2B1.527 (4)
C1A—C10A1.535 (3)C1B—C10B1.552 (4)
C2A—C3A1.511 (3)C2B—C3B1.506 (6)
C3A—C4A1.529 (3)C3B—C4B1.517 (4)
C4A—C24A1.529 (3)C4B—C24B1.533 (5)
C4A—C23A1.540 (3)C4B—C23B1.538 (5)
C4A—C5A1.550 (3)C4B—C5B1.554 (4)
C5A—C6A1.519 (3)C5B—C6B1.510 (4)
C5A—C10A1.563 (3)C5B—C10B1.555 (4)
C6A—C7A1.516 (3)C6B—C7B1.516 (4)
C7A—C8A1.544 (3)C7B—C8B1.531 (3)
C8A—C26A1.540 (4)C8B—C9B1.545 (3)
C8A—C9A1.548 (3)C8B—C26B1.555 (3)
C8A—C14A1.596 (3)C8B—C14B1.578 (3)
C9A—C11A1.540 (3)C9B—C11B1.519 (3)
C9A—C10A1.569 (3)C9B—C10B1.555 (4)
C10A—C25A1.534 (3)C10B—C25B1.536 (4)
C11A—C12A1.498 (4)C11B—C12B1.501 (4)
C12A—C13A1.504 (3)C12B—C13B1.513 (3)
C13A—C18A1.542 (3)C13B—C18B1.537 (4)
C13A—C14A1.555 (3)C13B—C14B1.548 (3)
C14A—C27A1.547 (3)C14B—C15B1.541 (3)
C14A—C15A1.547 (3)C14B—C27B1.555 (3)
C15A—C16A1.515 (4)C15B—C16B1.509 (4)
C16A—C17A1.544 (5)C16B—C17B1.528 (4)
C17A—C28A1.515 (5)C17B—C28B1.527 (4)
C17A—C18A1.546 (4)C17B—C22B1.535 (4)
C17A—C22A1.566 (4)C17B—C18B1.537 (3)
C18A—C19A1.518 (4)C18B—C19B1.537 (4)
C19A—C20A1.528 (4)C19B—C20B1.526 (4)
C20A—C30A1.518 (6)C20B—C21B1.513 (4)
C20A—C29A1.520 (5)C20B—C29B1.521 (6)
C20A—C21A1.541 (5)C20B—C30B1.541 (5)
C21A—C22A1.480 (6)C21B—C22B1.533 (5)
C31A—C32A1.479 (4)C31B—C32B1.468 (7)
C31A—O1A—C3A117.76 (19)C31B—O1B—C3B119.6 (4)
C28A—O5A—C33A117.0 (4)C28B—O5B—C33B115.8 (3)
C2A—C1A—C10A113.33 (19)C2B—C1B—C10B112.6 (2)
C3A—C2A—C1A109.97 (18)C3B—C2B—C1B110.6 (3)
O1A—C3A—C2A110.10 (18)O1B—C3B—C2B108.4 (3)
O1A—C3A—C4A108.42 (17)O1B—C3B—C4B108.5 (2)
C2A—C3A—C4A113.7 (2)C2B—C3B—C4B114.1 (3)
C3A—C4A—C24A111.58 (18)C3B—C4B—C24B111.4 (3)
C3A—C4A—C23A106.7 (2)C3B—C4B—C23B107.4 (3)
C24A—C4A—C23A107.9 (2)C24B—C4B—C23B108.3 (2)
C3A—C4A—C5A106.57 (17)C3B—C4B—C5B106.4 (2)
C24A—C4A—C5A114.9 (2)C24B—C4B—C5B113.9 (3)
C23A—C4A—C5A108.87 (18)C23B—C4B—C5B109.1 (3)
C6A—C5A—C4A114.99 (17)C6B—C5B—C4B114.1 (2)
C6A—C5A—C10A109.79 (18)C6B—C5B—C10B111.0 (2)
C4A—C5A—C10A117.58 (17)C4B—C5B—C10B117.8 (2)
C7A—C6A—C5A111.53 (19)C5B—C6B—C7B111.3 (2)
C6A—C7A—C8A114.20 (18)C6B—C7B—C8B114.6 (2)
C26A—C8A—C7A107.2 (2)C7B—C8B—C9B109.45 (19)
C26A—C8A—C9A111.9 (2)C7B—C8B—C26B106.5 (2)
C7A—C8A—C9A108.91 (18)C9B—C8B—C26B111.3 (2)
C26A—C8A—C14A111.31 (19)C7B—C8B—C14B111.3 (2)
C7A—C8A—C14A110.31 (19)C9B—C8B—C14B107.89 (17)
C9A—C8A—C14A107.22 (18)C26B—C8B—C14B110.4 (2)
C11A—C9A—C8A110.56 (19)C11B—C9B—C8B111.5 (2)
C11A—C9A—C10A113.42 (17)C11B—C9B—C10B113.8 (2)
C8A—C9A—C10A117.46 (18)C8B—C9B—C10B116.94 (19)
C25A—C10A—C1A107.74 (19)C25B—C10B—C1B107.6 (3)
C25A—C10A—C5A113.65 (19)C25B—C10B—C5B114.0 (2)
C1A—C10A—C5A108.10 (19)C1B—C10B—C5B107.7 (2)
C25A—C10A—C9A113.6 (2)C25B—C10B—C9B113.7 (2)
C1A—C10A—C9A108.48 (18)C1B—C10B—C9B108.1 (2)
C5A—C10A—C9A105.04 (16)C5B—C10B—C9B105.5 (2)
C12A—C11A—C9A116.46 (19)C12B—C11B—C9B117.6 (2)
O3A—C12A—C11A119.6 (2)O3B—C12B—C11B119.8 (2)
O3A—C12A—C13A122.3 (2)O3B—C12B—C13B122.8 (2)
C11A—C12A—C13A117.9 (2)C11B—C12B—C13B117.2 (2)
C12A—C13A—C18A114.5 (2)C12B—C13B—C18B115.12 (19)
C12A—C13A—C14A111.49 (19)C12B—C13B—C14B110.48 (19)
C18A—C13A—C14A117.2 (2)C18B—C13B—C14B118.0 (2)
C27A—C14A—C15A109.1 (2)C15B—C14B—C13B109.42 (18)
C27A—C14A—C13A109.9 (2)C15B—C14B—C27B106.5 (2)
C15A—C14A—C13A108.7 (2)C13B—C14B—C27B109.90 (19)
C27A—C14A—C8A110.89 (19)C15B—C14B—C8B111.62 (18)
C15A—C14A—C8A110.73 (19)C13B—C14B—C8B108.26 (19)
C13A—C14A—C8A107.51 (18)C27B—C14B—C8B111.13 (18)
C16A—C15A—C14A114.3 (2)C16B—C15B—C14B114.72 (19)
C15A—C16A—C17A112.4 (2)C15B—C16B—C17B112.7 (2)
C28A—C17A—C16A112.2 (3)C28B—C17B—C16B110.8 (2)
C28A—C17A—C18A110.4 (3)C28B—C17B—C22B104.0 (2)
C16A—C17A—C18A108.9 (2)C16B—C17B—C22B111.3 (2)
C28A—C17A—C22A105.0 (3)C28B—C17B—C18B110.1 (2)
C16A—C17A—C22A111.2 (3)C16B—C17B—C18B108.81 (19)
C18A—C17A—C22A109.2 (2)C22B—C17B—C18B111.7 (2)
C19A—C18A—C13A116.3 (2)C17B—C18B—C13B109.8 (2)
C19A—C18A—C17A112.3 (2)C17B—C18B—C19B111.1 (2)
C13A—C18A—C17A108.9 (2)C13B—C18B—C19B116.7 (2)
C18A—C19A—C20A114.3 (3)C20B—C19B—C18B113.9 (2)
C30A—C20A—C29A108.1 (3)C21B—C20B—C29B108.9 (3)
C30A—C20A—C19A112.0 (3)C21B—C20B—C19B108.6 (2)
C29A—C20A—C19A109.2 (3)C29B—C20B—C19B108.4 (3)
C30A—C20A—C21A111.4 (3)C21B—C20B—C30B110.9 (3)
C29A—C20A—C21A109.1 (3)C29B—C20B—C30B109.1 (3)
C19A—C20A—C21A107.1 (3)C19B—C20B—C30B110.9 (3)
C22A—C21A—C20A113.6 (3)C20B—C21B—C22B112.6 (3)
C21A—C22A—C17A115.4 (3)C21B—C22B—C17B113.7 (2)
O4A—C28A—O5A121.6 (4)O4B—C28B—O5B121.7 (3)
O4A—C28A—C17A125.6 (3)O4B—C28B—C17B126.3 (3)
O5A—C28A—C17A112.7 (4)O5B—C28B—C17B112.1 (2)
O2A—C31A—O1A123.0 (3)O2B—C31B—O1B121.5 (5)
O2A—C31A—C32A124.3 (3)O2B—C31B—C32B126.8 (6)
O1A—C31A—C32A112.7 (2)O1B—C31B—C32B111.4 (7)
C10A—C1A—C2A—C3A57.8 (3)C10B—C1B—C2B—C3B57.3 (4)
C31A—O1A—C3A—C2A81.8 (2)C31B—O1B—C3B—C2B105.4 (5)
C31A—O1A—C3A—C4A153.3 (2)C31B—O1B—C3B—C4B130.2 (5)
C1A—C2A—C3A—O1A177.49 (19)C1B—C2B—C3B—O1B178.5 (3)
C1A—C2A—C3A—C4A60.7 (3)C1B—C2B—C3B—C4B60.5 (4)
O1A—C3A—C4A—C24A52.2 (2)O1B—C3B—C4B—C24B51.4 (4)
C2A—C3A—C4A—C24A70.6 (3)C2B—C3B—C4B—C24B69.5 (3)
O1A—C3A—C4A—C23A65.4 (2)O1B—C3B—C4B—C23B67.1 (4)
C2A—C3A—C4A—C23A171.77 (19)C2B—C3B—C4B—C23B172.0 (3)
O1A—C3A—C4A—C5A178.32 (17)O1B—C3B—C4B—C5B176.2 (3)
C2A—C3A—C4A—C5A55.5 (2)C2B—C3B—C4B—C5B55.2 (4)
C3A—C4A—C5A—C6A176.78 (19)C3B—C4B—C5B—C6B175.0 (3)
C24A—C4A—C5A—C6A59.1 (2)C24B—C4B—C5B—C6B61.9 (4)
C23A—C4A—C5A—C6A62.0 (3)C23B—C4B—C5B—C6B59.3 (3)
C3A—C4A—C5A—C10A51.5 (2)C3B—C4B—C5B—C10B52.2 (3)
C24A—C4A—C5A—C10A72.6 (2)C24B—C4B—C5B—C10B71.0 (3)
C3A—C4A—C5A—C10A166.3 (2)C23B—C4B—C5B—C10B167.8 (2)
C4A—C5A—C6A—C7A161.30 (19)C4B—C5B—C6B—C7B162.6 (2)
C10A—C5A—C6A—C7A63.4 (2)C10B—C5B—C6B—C7B61.4 (3)
C5A—C6A—C7A—C8A55.9 (3)C5B—C6B—C7B—C8B54.2 (3)
C6A—C7A—C8A—C26A75.0 (3)C6B—C7B—C8B—C9B46.1 (3)
C6A—C7A—C8A—C9A46.2 (3)C6B—C7B—C8B—C26B74.3 (3)
C6A—C7A—C8A—C14A163.6 (2)C6B—C7B—C8B—C14B165.3 (2)
C26A—C8A—C9A—C11A62.8 (3)C7B—C8B—C9B—C11B177.5 (2)
C7A—C8A—C9A—C11A178.8 (2)C26B—C8B—C9B—C11B65.0 (3)
C14A—C8A—C9A—C11A59.5 (2)C14B—C8B—C9B—C11B56.2 (3)
C26A—C8A—C9A—C10A69.5 (3)C7B—C8B—C9B—C10B49.0 (3)
C7A—C8A—C9A—C10A48.8 (3)C26B—C8B—C9B—C10B68.4 (3)
C14A—C8A—C9A—C10A168.17 (18)C14B—C8B—C9B—C10B170.34 (19)
C2A—C1A—C10A—C25A72.1 (3)C2B—C1B—C10B—C25B72.2 (4)
C2A—C1A—C10A—C5A51.1 (3)C2B—C1B—C10B—C5B51.1 (4)
C2A—C1A—C10A—C9A164.47 (19)C2B—C1B—C10B—C9B164.6 (3)
C6A—C5A—C10A—C25A64.5 (2)C6B—C5B—C10B—C25B65.8 (3)
C4A—C5A—C10A—C25A69.5 (3)C4B—C5B—C10B—C25B68.5 (3)
C6A—C5A—C10A—C1A175.99 (18)C6B—C5B—C10B—C1B174.9 (2)
C4A—C5A—C10A—C1A50.0 (3)C4B—C5B—C10B—C1B50.9 (3)
C6A—C5A—C10A—C9A60.3 (2)C6B—C5B—C10B—C9B59.6 (3)
C4A—C5A—C10A—C9A165.69 (18)C4B—C5B—C10B—C9B166.1 (2)
C11A—C9A—C10A—C25A62.2 (3)C11B—C9B—C10B—C25B62.2 (3)
C8A—C9A—C10A—C25A68.9 (2)C8B—C9B—C10B—C25B70.2 (3)
C11A—C9A—C10A—C1A57.6 (3)C11B—C9B—C10B—C1B57.2 (3)
C8A—C9A—C10A—C1A171.35 (19)C8B—C9B—C10B—C1B170.4 (2)
C11A—C9A—C10A—C5A173.0 (2)C11B—C9B—C10B—C5B172.2 (2)
C8A—C9A—C10A—C5A55.9 (2)C8B—C9B—C10B—C5B55.4 (3)
C8A—C9A—C11A—C12A44.2 (3)C8B—C9B—C11B—C12B41.1 (3)
C10A—C9A—C11A—C12A178.6 (2)C10B—C9B—C11B—C12B176.0 (2)
C9A—C11A—C12A—O3A149.4 (3)C9B—C11B—C12B—O3B150.1 (3)
C9A—C11A—C12A—C13A35.8 (3)C9B—C11B—C12B—C13B34.8 (4)
O3A—C12A—C13A—C18A6.8 (4)O3B—C12B—C13B—C18B4.9 (4)
C11A—C12A—C13A—C18A178.6 (2)C11B—C12B—C13B—C18B179.8 (2)
O3A—C12A—C13A—C14A142.7 (2)O3B—C12B—C13B—C14B141.6 (3)
C11A—C12A—C13A—C14A42.6 (3)C11B—C12B—C13B—C14B43.5 (3)
C12A—C13A—C14A—C27A63.2 (3)C12B—C13B—C14B—C15B179.1 (2)
C18A—C13A—C14A—C27A71.5 (3)C18B—C13B—C14B—C15B43.7 (3)
C12A—C13A—C14A—C15A177.5 (2)C12B—C13B—C14B—C27B62.5 (3)
C18A—C13A—C14A—C15A47.8 (3)C18B—C13B—C14B—C27B72.9 (3)
C12A—C13A—C14A—C8A57.6 (3)C12B—C13B—C14B—C8B59.1 (2)
C18A—C13A—C14A—C8A167.7 (2)C18B—C13B—C14B—C8B165.55 (19)
C26A—C8A—C14A—C27A175.7 (2)C7B—C8B—C14B—C15B52.9 (2)
C7A—C8A—C14A—C27A65.4 (2)C9B—C8B—C14B—C15B173.03 (18)
C9A—C8A—C14A—C27A53.1 (2)C26B—C8B—C14B—C15B65.2 (2)
C26A—C8A—C14A—C15A63.0 (3)C7B—C8B—C14B—C13B173.40 (18)
C7A—C8A—C14A—C15A55.9 (3)C9B—C8B—C14B—C13B66.5 (2)
C9A—C8A—C14A—C15A174.4 (2)C26B—C8B—C14B—C13B55.3 (2)
C26A—C8A—C14A—C13A55.6 (2)C7B—C8B—C14B—C27B65.8 (2)
C7A—C8A—C14A—C13A174.52 (19)C9B—C8B—C14B—C27B54.3 (2)
C9A—C8A—C14A—C13A67.0 (2)C26B—C8B—C14B—C27B176.1 (2)
C27A—C14A—C15A—C16A72.8 (3)C13B—C14B—C15B—C16B44.3 (3)
C13A—C14A—C15A—C16A47.0 (3)C27B—C14B—C15B—C16B74.5 (2)
C8A—C14A—C15A—C16A164.8 (2)C8B—C14B—C15B—C16B164.07 (19)
C14A—C15A—C16A—C17A55.9 (3)C14B—C15B—C16B—C17B55.5 (3)
C15A—C16A—C17A—C28A62.5 (3)C15B—C16B—C17B—C28B60.9 (3)
C15A—C16A—C17A—C18A59.9 (3)C15B—C16B—C17B—C22B176.1 (2)
C15A—C16A—C17A—C22A179.8 (3)C15B—C16B—C17B—C18B60.4 (3)
C12A—C13A—C18A—C19A59.7 (3)C28B—C17B—C18B—C13B65.3 (3)
C14A—C13A—C18A—C19A73.7 (3)C16B—C17B—C18B—C13B56.3 (3)
C12A—C13A—C18A—C17A172.2 (2)C22B—C17B—C18B—C13B179.6 (2)
C14A—C13A—C18A—C17A54.5 (3)C28B—C17B—C18B—C19B164.0 (2)
C28A—C17A—C18A—C19A163.3 (2)C16B—C17B—C18B—C19B74.3 (3)
C16A—C17A—C18A—C19A73.2 (3)C22B—C17B—C18B—C19B49.0 (3)
C22A—C17A—C18A—C19A48.4 (4)C12B—C13B—C18B—C17B175.3 (2)
C28A—C17A—C18A—C13A66.4 (3)C14B—C13B—C18B—C17B51.3 (3)
C16A—C17A—C18A—C13A57.1 (3)C12B—C13B—C18B—C19B57.1 (3)
C22A—C17A—C18A—C13A178.7 (3)C14B—C13B—C18B—C19B76.3 (3)
C13A—C18A—C19A—C20A176.6 (2)C17B—C18B—C19B—C20B54.9 (3)
C17A—C18A—C19A—C20A56.9 (3)C13B—C18B—C19B—C20B178.2 (2)
C18A—C19A—C20A—C30A65.2 (4)C18B—C19B—C20B—C21B57.4 (4)
C18A—C19A—C20A—C29A175.1 (3)C18B—C19B—C20B—C29B175.5 (3)
C18A—C19A—C20A—C21A57.1 (4)C18B—C19B—C20B—C30B64.7 (3)
C30A—C20A—C21A—C22A68.0 (4)C29B—C20B—C21B—C22B173.3 (3)
C29A—C20A—C21A—C22A172.8 (4)C19B—C20B—C21B—C22B55.4 (4)
C19A—C20A—C21A—C22A54.7 (5)C30B—C20B—C21B—C22B66.7 (3)
C20A—C21A—C22A—C17A53.3 (5)C20B—C21B—C22B—C17B53.4 (3)
C28A—C17A—C22A—C21A166.5 (4)C28B—C17B—C22B—C21B168.0 (2)
C16A—C17A—C22A—C21A72.0 (4)C16B—C17B—C22B—C21B72.7 (3)
C18A—C17A—C22A—C21A48.1 (4)C18B—C17B—C22B—C21B49.2 (3)
C33A—O5A—C28A—O4A0.8 (6)C33B—O5B—C28B—O4B0.6 (5)
C33A—O5A—C28A—C17A176.3 (3)C33B—O5B—C28B—C17B178.1 (4)
C16A—C17A—C28A—O4A142.7 (4)C16B—C17B—C28B—O4B144.8 (3)
C18A—C17A—C28A—O4A21.1 (5)C22B—C17B—C28B—O4B95.5 (4)
C22A—C17A—C28A—O4A96.4 (4)C18B—C17B—C28B—O4B24.3 (4)
C16A—C17A—C28A—O5A40.4 (3)C16B—C17B—C28B—O5B36.7 (3)
C18A—C17A—C28A—O5A161.9 (3)C22B—C17B—C28B—O5B83.0 (3)
C22A—C17A—C28A—O5A80.5 (3)C18B—C17B—C28B—O5B157.1 (3)
C3A—O1A—C31A—O2A2.1 (3)C3B—O1B—C31B—O2B7.9 (11)
C3A—O1A—C31A—C32A176.4 (2)C3B—O1B—C31B—C32B177.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11B—H11D···O2Ai0.972.453.336 (4)152
C13A—H13A···O4A0.982.503.155 (4)124
C13B—H13B···O4B0.982.533.187 (3)124
C19A—H19A···O3A0.972.423.051 (3)122
C19B—H19D···O3B0.972.403.038 (3)123
C27B—H27E···O2Aii0.962.533.357 (4)145
Symmetry codes: (i) x, y1, z; (ii) x+1, y1, z.
(II) Methyl 3β-acetoxy-12,19-dioxoolean-9(11),13 (18)-dien-28-oate top
Crystal data top
C33H46O6F(000) = 584
Mr = 538.70Dx = 1.183 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 7.9348 (8) ÅCell parameters from 50 reflections
b = 15.8841 (10) Åθ = 14.8–30.2°
c = 12.1480 (8) ŵ = 0.64 mm1
β = 99.041 (7)°T = 293 K
V = 1512.1 (2) Å3Prism, colourless
Z = 20.53 × 0.40 × 0.20 mm
Data collection top
Kuma Diffraction KM-4
diffractometer
5157 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 70.2°, θmin = 3.7°
ω/2θ scansh = 98
Absorption correction: ψ-scan
(North et al., 1968)
k = 1919
Tmin = 0.769, Tmax = 0.880l = 014
5476 measured reflections2 standard reflections every 100 reflections
5362 independent reflections intensity decay: 1.7%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0534P)2 + 0.1609P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max = 0.007
S = 1.06Δρmax = 0.16 e Å3
5362 reflectionsΔρmin = 0.15 e Å3
362 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0059 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.00 (15)
Crystal data top
C33H46O6V = 1512.1 (2) Å3
Mr = 538.70Z = 2
Monoclinic, P21Cu Kα radiation
a = 7.9348 (8) ŵ = 0.64 mm1
b = 15.8841 (10) ÅT = 293 K
c = 12.1480 (8) Å0.53 × 0.40 × 0.20 mm
β = 99.041 (7)°
Data collection top
Kuma Diffraction KM-4
diffractometer
5157 reflections with I > 2σ(I)
Absorption correction: ψ-scan
(North et al., 1968)
Rint = 0.023
Tmin = 0.769, Tmax = 0.8802 standard reflections every 100 reflections
5476 measured reflections intensity decay: 1.7%
5362 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092Δρmax = 0.16 e Å3
S = 1.06Δρmin = 0.15 e Å3
5362 reflectionsAbsolute structure: Flack (1983)
362 parametersAbsolute structure parameter: 0.00 (15)
1 restraint
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
xyzUiso*/Ueq
O10.21451 (17)0.55406 (8)0.66832 (10)0.0593 (3)
O20.3845 (2)0.54561 (11)0.79746 (15)0.0908 (5)
O30.09466 (16)0.02786 (8)0.79924 (15)0.0776 (5)
O40.0972 (2)0.10255 (9)0.70074 (10)0.0794 (5)
O50.6296 (2)0.13339 (10)0.81373 (15)0.0829 (5)
O60.51164 (17)0.03240 (10)0.70121 (10)0.0673 (4)
C10.1905 (2)0.31773 (11)0.67054 (15)0.0535 (4)
H1A0.26310.27560.62910.064*
H1B0.19830.31090.74890.064*
C20.2544 (2)0.40533 (12)0.63256 (16)0.0587 (4)
H2A0.24890.41240.55390.070*
H2B0.37230.41180.64320.070*
C30.1461 (2)0.47068 (11)0.69874 (14)0.0505 (4)
H3A0.15080.46140.77800.061*
C40.0410 (2)0.46894 (10)0.68189 (14)0.0483 (3)
C50.10629 (19)0.37714 (9)0.70842 (12)0.0417 (3)
H5A0.10510.37030.78850.050*
C60.2918 (2)0.36398 (10)0.69473 (15)0.0515 (4)
H6A0.29960.35610.61650.062*
H6B0.35810.41340.72100.062*
C70.3637 (2)0.28714 (10)0.76072 (16)0.0520 (4)
H7A0.37160.29960.83950.062*
H7B0.47870.27730.74580.062*
C80.25957 (18)0.20516 (9)0.73558 (12)0.0402 (3)
C90.06651 (18)0.22143 (9)0.71069 (11)0.0391 (3)
C100.00415 (19)0.30333 (9)0.65292 (12)0.0423 (3)
C110.04033 (19)0.16081 (10)0.73254 (14)0.0482 (3)
H11A0.15670.17130.71470.058*
C120.0117 (2)0.07969 (9)0.78201 (14)0.0480 (3)
C130.19797 (18)0.06521 (9)0.81609 (11)0.0377 (3)
C140.30427 (18)0.14448 (9)0.83941 (11)0.0380 (3)
C150.49523 (19)0.12273 (10)0.85929 (14)0.0466 (3)
H15A0.53260.11340.78800.056*
H15B0.55880.17020.89480.056*
C160.5356 (2)0.04522 (11)0.93160 (14)0.0507 (4)
H16A0.50590.05631.00470.061*
H16B0.65740.03460.94100.061*
C170.4402 (2)0.03397 (10)0.88293 (12)0.0443 (3)
C180.25840 (18)0.01318 (9)0.83012 (10)0.0380 (3)
C190.1516 (2)0.08985 (9)0.79642 (12)0.0438 (3)
C200.1377 (2)0.15324 (10)0.88818 (14)0.0510 (4)
C210.3225 (3)0.17453 (12)0.94023 (18)0.0651 (5)
H21A0.32000.21071.00430.078*
H21B0.37540.20600.88630.078*
C220.4321 (2)0.09837 (12)0.97692 (15)0.0601 (4)
H22A0.54700.11721.00540.072*
H22B0.38740.07071.03740.072*
C230.1392 (3)0.52821 (12)0.7689 (2)0.0713 (5)
H23A0.25750.52890.76050.086*
H23B0.12830.50880.84230.086*
H23C0.09310.58400.75830.086*
C240.0627 (3)0.49946 (12)0.56554 (17)0.0660 (5)
H24A0.00070.46350.51040.079*
H24B0.18130.49790.55810.079*
H24C0.02110.55610.55510.079*
C250.0049 (3)0.29330 (12)0.52662 (14)0.0621 (4)
H25A0.10940.29870.51080.074*
H25B0.07560.33610.48720.074*
H25C0.04900.23880.50310.074*
C260.3089 (2)0.16279 (12)0.63033 (14)0.0567 (4)
H26A0.25700.10810.62080.068*
H26B0.43070.15710.63880.068*
H26C0.26970.19690.56620.068*
C270.2557 (2)0.18357 (10)0.94685 (13)0.0495 (4)
H27A0.13810.20050.93340.059*
H27B0.32640.23180.96800.059*
H27C0.27240.14271.00570.059*
C280.5381 (2)0.07352 (11)0.79715 (15)0.0524 (4)
C290.0445 (3)0.23155 (12)0.8402 (2)0.0741 (6)
H29A0.04700.27320.89770.089*
H29B0.09930.25340.78120.089*
H29C0.07180.21760.81140.089*
C300.0427 (3)0.11365 (14)0.97568 (16)0.0657 (5)
H30A0.07420.10400.94360.079*
H30B0.09550.06111.00020.079*
H30C0.04710.15111.03810.079*
C310.3343 (2)0.58312 (12)0.72457 (16)0.0591 (4)
C320.3974 (4)0.66756 (15)0.6834 (2)0.0868 (7)
H32A0.46470.66190.61090.104*
H32B0.30190.70380.67880.104*
H32C0.46610.69130.73390.104*
C330.6086 (3)0.0621 (2)0.6175 (2)0.0969 (9)
H33A0.72760.06340.64820.116*
H33B0.59110.02480.55450.116*
H33C0.57130.11770.59430.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0627 (7)0.0506 (7)0.0693 (7)0.0175 (5)0.0252 (6)0.0143 (5)
O20.1008 (12)0.0907 (11)0.0935 (10)0.0298 (10)0.0541 (9)0.0193 (9)
O30.0403 (7)0.0520 (7)0.1358 (13)0.0097 (5)0.0004 (7)0.0288 (8)
O40.1217 (13)0.0654 (8)0.0466 (6)0.0336 (8)0.0010 (7)0.0070 (6)
O50.0647 (9)0.0624 (8)0.1261 (13)0.0229 (7)0.0288 (8)0.0061 (8)
O60.0606 (8)0.0871 (9)0.0575 (7)0.0111 (7)0.0200 (6)0.0093 (6)
C10.0356 (8)0.0489 (9)0.0734 (10)0.0005 (6)0.0007 (7)0.0134 (8)
C20.0385 (9)0.0567 (10)0.0788 (11)0.0065 (7)0.0027 (8)0.0156 (8)
C30.0501 (9)0.0473 (8)0.0568 (8)0.0106 (7)0.0166 (7)0.0133 (7)
C40.0455 (9)0.0412 (8)0.0603 (9)0.0018 (6)0.0146 (7)0.0045 (7)
C50.0384 (8)0.0406 (7)0.0477 (7)0.0011 (6)0.0118 (6)0.0042 (6)
C60.0386 (8)0.0435 (8)0.0757 (11)0.0047 (6)0.0190 (7)0.0052 (7)
C70.0330 (8)0.0442 (8)0.0785 (11)0.0047 (6)0.0076 (7)0.0048 (7)
C80.0351 (7)0.0389 (7)0.0473 (7)0.0008 (5)0.0089 (6)0.0005 (5)
C90.0333 (7)0.0414 (7)0.0419 (7)0.0001 (5)0.0031 (5)0.0011 (5)
C100.0383 (8)0.0419 (7)0.0460 (7)0.0009 (6)0.0040 (6)0.0059 (6)
C110.0316 (7)0.0447 (8)0.0657 (9)0.0015 (6)0.0004 (6)0.0069 (7)
C120.0360 (8)0.0399 (7)0.0665 (9)0.0034 (6)0.0028 (7)0.0055 (6)
C130.0336 (7)0.0405 (7)0.0384 (6)0.0003 (5)0.0035 (5)0.0004 (5)
C140.0309 (7)0.0383 (7)0.0438 (7)0.0002 (5)0.0023 (5)0.0040 (5)
C150.0303 (7)0.0455 (8)0.0615 (8)0.0017 (6)0.0006 (6)0.0054 (7)
C160.0397 (8)0.0528 (9)0.0557 (8)0.0064 (7)0.0050 (6)0.0050 (7)
C170.0392 (8)0.0443 (7)0.0480 (7)0.0075 (6)0.0028 (6)0.0001 (6)
C180.0383 (7)0.0409 (7)0.0344 (6)0.0016 (6)0.0047 (5)0.0003 (5)
C190.0479 (8)0.0383 (7)0.0454 (7)0.0014 (6)0.0077 (6)0.0032 (6)
C200.0545 (9)0.0414 (8)0.0570 (9)0.0005 (7)0.0090 (7)0.0062 (6)
C210.0598 (11)0.0513 (10)0.0831 (12)0.0098 (8)0.0077 (9)0.0216 (9)
C220.0523 (10)0.0626 (10)0.0615 (10)0.0092 (8)0.0033 (8)0.0171 (8)
C230.0644 (13)0.0477 (9)0.1008 (15)0.0004 (8)0.0102 (11)0.0135 (10)
C240.0730 (12)0.0517 (10)0.0812 (12)0.0084 (8)0.0367 (10)0.0200 (9)
C250.0809 (13)0.0566 (10)0.0462 (9)0.0065 (9)0.0023 (8)0.0053 (7)
C260.0595 (10)0.0626 (10)0.0516 (8)0.0103 (8)0.0196 (7)0.0015 (7)
C270.0526 (9)0.0483 (8)0.0472 (8)0.0025 (7)0.0068 (7)0.0065 (6)
C280.0400 (8)0.0497 (9)0.0684 (10)0.0034 (7)0.0110 (7)0.0092 (7)
C290.0787 (14)0.0436 (9)0.1010 (16)0.0081 (9)0.0174 (12)0.0052 (9)
C300.0632 (12)0.0778 (13)0.0594 (10)0.0017 (10)0.0198 (8)0.0075 (9)
C310.0585 (10)0.0590 (10)0.0624 (10)0.0091 (8)0.0173 (8)0.0012 (8)
C320.0933 (17)0.0647 (13)0.1067 (17)0.0278 (12)0.0289 (14)0.0013 (12)
C330.0716 (14)0.151 (3)0.0755 (13)0.0003 (16)0.0337 (11)0.0333 (15)
Geometric parameters (Å, º) top
O1—C311.337 (2)C9—C111.337 (2)
O1—C31.4567 (19)C9—C101.5413 (19)
O2—C311.187 (2)C10—C251.542 (2)
O3—C121.2202 (19)C11—C121.454 (2)
O4—C191.1918 (19)C12—C131.489 (2)
O5—C281.194 (2)C13—C181.336 (2)
O6—C281.324 (2)C13—C141.5172 (19)
O6—C331.447 (2)C14—C151.536 (2)
C1—C21.527 (2)C14—C271.548 (2)
C1—C101.544 (2)C15—C161.517 (2)
C2—C31.498 (3)C16—C171.538 (2)
C3—C41.530 (2)C17—C181.520 (2)
C4—C241.529 (2)C17—C281.529 (2)
C4—C231.534 (3)C17—C221.542 (2)
C4—C51.564 (2)C18—C191.503 (2)
C5—C61.522 (2)C19—C201.519 (2)
C5—C101.553 (2)C20—C291.516 (3)
C6—C71.521 (2)C20—C301.531 (3)
C7—C81.547 (2)C20—C211.541 (3)
C8—C91.536 (2)C21—C221.515 (3)
C8—C261.549 (2)C31—C321.490 (3)
C8—C141.5828 (19)
C31—O1—C3116.77 (13)C18—C13—C12120.02 (13)
C28—O6—C33115.45 (18)C18—C13—C14124.89 (13)
C2—C1—C10111.88 (13)C12—C13—C14114.98 (12)
C3—C2—C1109.51 (14)C13—C14—C15110.40 (11)
O1—C3—C2109.54 (14)C13—C14—C27106.59 (12)
O1—C3—C4108.23 (13)C15—C14—C27109.15 (12)
C2—C3—C4113.71 (14)C13—C14—C8107.95 (11)
C24—C4—C3111.75 (15)C15—C14—C8110.75 (11)
C24—C4—C23108.87 (16)C27—C14—C8111.93 (12)
C3—C4—C23107.17 (14)C16—C15—C14112.75 (13)
C24—C4—C5113.83 (13)C15—C16—C17113.27 (12)
C3—C4—C5106.64 (12)C18—C17—C28110.60 (12)
C23—C4—C5108.32 (14)C18—C17—C16111.20 (12)
C6—C5—C10109.79 (12)C28—C17—C16109.02 (13)
C6—C5—C4113.61 (12)C18—C17—C22108.06 (13)
C10—C5—C4117.92 (12)C28—C17—C22108.46 (13)
C7—C6—C5109.99 (12)C16—C17—C22109.46 (13)
C6—C7—C8115.26 (13)C13—C18—C19123.01 (13)
C9—C8—C7112.50 (12)C13—C18—C17123.67 (13)
C9—C8—C26106.52 (12)C19—C18—C17113.32 (12)
C7—C8—C26109.41 (13)O4—C19—C18120.33 (14)
C9—C8—C14110.55 (11)O4—C19—C20123.14 (15)
C7—C8—C14108.02 (12)C18—C19—C20116.10 (12)
C26—C8—C14109.83 (12)C29—C20—C19110.43 (15)
C11—C9—C8118.93 (13)C29—C20—C30109.89 (16)
C11—C9—C10120.11 (13)C19—C20—C30109.72 (13)
C8—C9—C10120.79 (12)C29—C20—C21110.67 (15)
C9—C10—C25108.07 (12)C19—C20—C21105.82 (14)
C9—C10—C1110.47 (12)C30—C20—C21110.24 (15)
C25—C10—C1107.41 (13)C22—C21—C20114.25 (14)
C9—C10—C5107.42 (11)C21—C22—C17113.61 (14)
C25—C10—C5115.07 (13)O5—C28—O6123.35 (17)
C1—C10—C5108.38 (12)O5—C28—C17124.94 (18)
C9—C11—C12124.94 (14)O6—C28—C17111.71 (13)
O3—C12—C11120.65 (14)O2—C31—O1123.84 (17)
O3—C12—C13122.08 (14)O2—C31—C32124.62 (18)
C11—C12—C13117.17 (13)O1—C31—C32111.53 (17)
C10—C1—C2—C360.68 (19)C18—C13—C14—C8132.20 (13)
C31—O1—C3—C287.89 (18)C12—C13—C14—C851.73 (15)
C31—O1—C3—C4147.63 (16)C9—C8—C14—C1354.82 (14)
C1—C2—C3—O1175.88 (13)C7—C8—C14—C13178.30 (12)
C1—C2—C3—C462.89 (18)C26—C8—C14—C1362.44 (15)
O1—C3—C4—C2451.67 (19)C9—C8—C14—C15175.78 (11)
C2—C3—C4—C2470.28 (18)C7—C8—C14—C1560.74 (14)
O1—C3—C4—C2367.52 (17)C26—C8—C14—C1558.52 (15)
C2—C3—C4—C23170.52 (15)C9—C8—C14—C2762.17 (15)
O1—C3—C4—C5176.66 (13)C7—C8—C14—C2761.31 (15)
C2—C3—C4—C554.70 (17)C26—C8—C14—C27179.44 (13)
C24—C4—C5—C655.8 (2)C13—C14—C15—C1642.27 (16)
C3—C4—C5—C6179.52 (14)C27—C14—C15—C1674.58 (15)
C23—C4—C5—C665.42 (18)C8—C14—C15—C16161.77 (12)
C24—C4—C5—C1074.71 (18)C14—C15—C16—C1758.47 (17)
C3—C4—C5—C1048.99 (17)C15—C16—C17—C1839.23 (18)
C23—C4—C5—C10164.05 (14)C15—C16—C17—C2882.97 (16)
C10—C5—C6—C766.45 (17)C15—C16—C17—C22158.55 (14)
C4—C5—C6—C7159.09 (13)C12—C13—C18—C199.7 (2)
C5—C6—C7—C853.56 (19)C14—C13—C18—C19174.43 (12)
C6—C7—C8—C935.29 (18)C12—C13—C18—C17169.41 (13)
C6—C7—C8—C2682.89 (17)C14—C13—C18—C176.5 (2)
C6—C7—C8—C14157.58 (13)C28—C17—C18—C13113.58 (15)
C7—C8—C9—C11152.60 (15)C16—C17—C18—C137.69 (19)
C26—C8—C9—C1187.53 (17)C22—C17—C18—C13127.85 (15)
C14—C8—C9—C1131.75 (19)C28—C17—C18—C1967.25 (16)
C7—C8—C9—C1032.20 (18)C16—C17—C18—C19171.47 (12)
C26—C8—C9—C1087.66 (16)C22—C17—C18—C1951.32 (16)
C14—C8—C9—C10153.06 (12)C13—C18—C19—O464.7 (2)
C11—C9—C10—C2594.47 (18)C17—C18—C19—O4116.15 (19)
C8—C9—C10—C2580.66 (16)C13—C18—C19—C20122.63 (15)
C11—C9—C10—C122.8 (2)C17—C18—C19—C2056.54 (17)
C8—C9—C10—C1162.09 (13)O4—C19—C20—C290.9 (3)
C11—C9—C10—C5140.80 (15)C18—C19—C20—C29173.34 (15)
C8—C9—C10—C544.06 (16)O4—C19—C20—C30122.2 (2)
C2—C1—C10—C9169.92 (13)C18—C19—C20—C3065.38 (18)
C2—C1—C10—C2572.43 (18)O4—C19—C20—C21118.9 (2)
C2—C1—C10—C552.47 (18)C18—C19—C20—C2153.54 (18)
C6—C5—C10—C959.43 (15)C29—C20—C21—C22172.50 (17)
C4—C5—C10—C9168.31 (12)C19—C20—C21—C2252.9 (2)
C6—C5—C10—C2560.95 (17)C30—C20—C21—C2265.7 (2)
C4—C5—C10—C2571.31 (17)C20—C21—C22—C1756.0 (2)
C6—C5—C10—C1178.81 (12)C18—C17—C22—C2151.92 (18)
C4—C5—C10—C148.93 (16)C28—C17—C22—C2168.01 (18)
C8—C9—C11—C121.9 (3)C16—C17—C22—C21173.16 (14)
C10—C9—C11—C12177.13 (14)C33—O6—C28—O53.1 (3)
C9—C11—C12—O3179.93 (19)C33—O6—C28—C17175.98 (17)
C9—C11—C12—C133.3 (3)C18—C17—C28—O5136.23 (18)
O3—C12—C13—C1823.6 (3)C16—C17—C28—O5101.21 (19)
C11—C12—C13—C18159.91 (14)C22—C17—C28—O517.9 (2)
O3—C12—C13—C14152.73 (17)C18—C17—C28—O644.73 (18)
C11—C12—C13—C1423.8 (2)C16—C17—C28—O677.83 (16)
C18—C13—C14—C1511.01 (18)C22—C17—C28—O6163.06 (14)
C12—C13—C14—C15172.91 (13)C3—O1—C31—O21.1 (3)
C18—C13—C14—C27107.40 (15)C3—O1—C31—C32178.25 (19)
C12—C13—C14—C2768.67 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15A···O60.972.543.139 (2)120
C25—H25B···O4i0.962.463.204 (2)134
C33—H33A···O3ii0.962.583.290 (3)131
Symmetry codes: (i) x, y+1/2, z+1; (ii) x+1, y, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC33H52O5C33H46O6
Mr528.75538.70
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21
Temperature (K)293293
a, b, c (Å)7.0662 (16), 22.083 (3), 40.141 (5)7.9348 (8), 15.8841 (10), 12.1480 (8)
α, β, γ (°)90, 90, 9090, 99.041 (7), 90
V3)6263.7 (18)1512.1 (2)
Z82
Radiation typeCu KαCu Kα
µ (mm1)0.580.64
Crystal size (mm)0.50 × 0.14 × 0.090.53 × 0.40 × 0.20
Data collection
DiffractometerKuma Diffraction KM-4
diffractometer
Kuma Diffraction KM-4
diffractometer
Absorption correctionψ-scan
(North et al., 1968)
Tmin, Tmax0.769, 0.880
No. of measured, independent and
observed [I > 2σ(I)] reflections
10738, 10265, 7013 5476, 5362, 5157
Rint0.0170.023
(sin θ/λ)max1)0.5880.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.130, 1.08 0.032, 0.092, 1.06
No. of reflections102655362
No. of parameters704362
No. of restraints01
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.180.16, 0.15
Absolute structureFlack (1983)Flack (1983)
Absolute structure parameter0.0 (2)0.00 (15)

Computer programs: KM-4 Software (Kuma Diffraction, 1991), KM-4 Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) for (I) top
C8A—C14A1.596 (3)C8B—C14B1.578 (3)
C9A—C11A1.540 (3)C9B—C11B1.519 (3)
C17A—C22A1.566 (4)C17B—C22B1.535 (4)
C20A—C21A1.541 (5)C20B—C21B1.513 (4)
C21A—C22A1.480 (6)C21B—C22B1.533 (5)
C31A—O1A—C3A117.76 (19)C31B—O1B—C3B119.6 (4)
O1A—C3A—C2A110.10 (18)O1B—C3B—C2B108.4 (3)
C6A—C5A—C10A109.79 (18)C6B—C5B—C10B111.0 (2)
C7A—C8A—C14A110.31 (19)C7B—C8B—C14B111.3 (2)
C12A—C11A—C9A116.46 (19)C12B—C11B—C9B117.6 (2)
C12A—C13A—C14A111.49 (19)C12B—C13B—C14B110.48 (19)
C27A—C14A—C15A109.1 (2)C15B—C14B—C27B106.5 (2)
C28A—C17A—C16A112.2 (3)C28B—C17B—C16B110.8 (2)
C18A—C17A—C22A109.2 (2)C22B—C17B—C18B111.7 (2)
C19A—C18A—C17A112.3 (2)C17B—C18B—C19B111.1 (2)
C19A—C20A—C21A107.1 (3)C21B—C20B—C19B108.6 (2)
C21A—C22A—C17A115.4 (3)C21B—C22B—C17B113.7 (2)
O2A—C31A—C32A124.3 (3)O2B—C31B—C32B126.8 (6)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
C11B—H11D···O2Ai0.972.453.336 (4)152
C13A—H13A···O4A0.982.503.155 (4)124
C13B—H13B···O4B0.982.533.187 (3)124
C19A—H19A···O3A0.972.423.051 (3)122
C19B—H19D···O3B0.972.403.038 (3)123
C27B—H27E···O2Aii0.962.533.357 (4)145
Symmetry codes: (i) x, y1, z; (ii) x+1, y1, z.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
C15—H15A···O60.972.543.139 (2)120
C25—H25B···O4i0.962.463.204 (2)134
C33—H33A···O3ii0.962.583.290 (3)131
Symmetry codes: (i) x, y+1/2, z+1; (ii) x+1, y, z.
 

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