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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Pages o342-o343
https://doi.org/10.1107/S1600536810000620

(+)-Hexacyclinol

David M. Pinkerton,a Martin G. Banwella* and Anthony C. Willisa

aResearch School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia
*Correspondence e-mail: mgb@rsc.anu.edu.au

(Received 6 January 2010; accepted 6 January 2010; online 13 January 2010)

A sample of the title compound [systematic name: (1aS,2aS,3S,5aS,6aS,7R,7aS,7bS,8R,8aS,10R)-7-hydr­oxy-3-(1-meth­oxy-1-methyl­ethyl)-10-(2-methyl-1-propen­yl)-1a,5a,6a,7,7a,7b,8,8a-octa­hydro-2H-8,2a-(epoxy­methano)phenanthro[2,3-b:6,7-b′]bis­oxirene-2,5(3H)-dione], C23H28O7, was generated by enanti­oselective synthesis. There are three mol­ecules of the compound in the crystallographic asymmetric unit. Hydrogen bonding between alcohol H atoms and keto groups of adjacent mol­ecules appears to stabilize the structure. The compound is enanti­omerically pure but the absolute configuration could not be determined directly in this study. Accordingly, the illustrated configuration was assigned on the basis of the nature of the chiral nonracemic precursor used in the synthesis.

Related literature

(+)-Hexacyclinol is a natural product that was first isolated and characterized by Schlegel et al. (2002[Schlegel, B., Härtl, A., Dahse, H.-M., Gollmick, F. A., Gräfe, U., Dörfelt, H. & Kappes, B. (2002). J. Antibiot. 55, 814-817.]). Rychnovsky (2006[Rychnovsky, S. D. (2006). Org. Lett. 8, 2895-2898.]) proposed the illustrated structure by re-evaluation of the derived 13C NMR spectral data. This structure was confirmed through the synthesis and X-ray analysis of racemic material (Porco et al., 2006[Porco, J. A. Jr, Su, S., Lei, X., Bardhan, S. & Rychnovsky, S. D. (2006). Angew. Chem. Int. Ed. 45, 5790-5792.]). Like others (Mehta & Roy, 2008[Mehta, G. & Roy, S. (2008). Tetrahedron Lett. 49, 1458-1460.]), we have recently completed a synthesis of (+)-hexa­cyclinol, in our case from an enzymatically generated and enanti­omerically pure cis-1,2-dihydro­catechol (Pinkerton et al., 2009[Pinkerton, D. M., Banwell, M. G. & Willis, A. C. (2009). Org. Lett. 11, 4290-4293.]).

[Scheme 1]

Experimental

Crystal data

  • C23H28O7

  • Mr = 416.47

  • Orthorhombic, P 21 21 21

  • a = 10.8270 (1) Å

  • b = 20.0530 (2) Å

  • c = 28.0247 (3) Å

  • V = 6084.55 (11) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 200 K

  • 0.42 × 0.18 × 0.15 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: integration [via Gaussian method (Coppens, 1970[Coppens, P. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 255-270. Copenhagen: Munksgaard.]) implemented in maXus (Mackay et al., 2000[Mackay, S., Edwards, C., Henderson, A., Gilmore, C., Stewart, N., Shankland, K. & Donald, A. (2000). maXus. University of Glasgow, Scotland, MacScience Co., Yokohama, Japan, and Nonius BV, Delft, The Netherlands.])] Tmin = 0.972, Tmax = 0.994

  • 80486 measured reflections

  • 7619 independent reflections

  • 5571 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.079

  • S = 0.83

  • 7619 reflections

  • 820 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.25 e Å−3

  • Absolute structure: the enantiomer has been assigned by reference to an unchanging centre of chirality in the starting material.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O30—H301⋯O121 0.91 (3) 1.92 (3) 2.828 (3) 172 (3)
O130—H1301⋯O21i 0.81 (3) 2.04 (3) 2.796 (3) 155 (3)
O230—H2301⋯O221ii 0.76 (3) 2.10 (3) 2.809 (3) 156 (3)
Symmetry codes: (i) x+1, y, z; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: COLLECT (Nonius, 2001[Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) in TEXSAN (Molecular Structure Corporation, 1997[Molecular Structure Corporation (1997). TEXSAN. MSC, The Woodlands, Texas, USA.]); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810000620/hg2629sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000620/hg2629Isup2.hkl

checkCIF report


Related literature top

(+)-Hexacyclinol is a natural product that was first isolated and characterized by Schlegel et al. (2002). Rychnovsky (2006) proposed the illustrated structure by re-evaluation of the derived 13C NMR spectral data. This structure was confirmed through the synthesis and X-ray analysis of racemic material (Porco et al., 2006). Like others (Mehta & Roy, 2008), we have recently completed a synthesis of (+)-hexacyclinol, in our case from an enzymatically generated and enantiomerically pure cis-1,2-dihydrocatechol (Pinkerton et al., 2009). We report herein the single-crystal X-ray analysis of this material.

Experimental top

(+)-Hexacyclinol was prepared according to a published procedure (Pinkerton et al., 2009) and crystals suitable for X-ray analysis grown from mixtures of dichloromethane and light-petroleum. The sample had m.p. = 176–178°C [lit., Mehta & Roy (2008) m.p. = 179–180°C], [α]D = +129.6 (c 0.36, methanol) {lit., Mehta & Roy (2008) [α]D = +130.9 (c 0.42, methanol)}.

Refinement top

The compound is enantiometrically pure but the anomolous dispersion terms are very low for all elements in the structure so the absolute configuration could not be determined in this experiment. Consequently, Friedel-pair reflections were averaged and the Flack parameter was not refined. The illustrated configuration was assigned on the basis of the nature of the chiral, non-racemic, precursor used in the synthesis.

H atoms attached to C were included at calculated positions (methyl groups oriented to best-match peaks in a difference electron density map) and those attached to O as indicated in the difference map. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, O—H = 0.82 Å) and with Uiso(H) in the range 1.2–1.5 times Ueq of the parent atom. Later, H atoms attached to C were refined with riding constraints and those attached to O were allowed to refine without restraints.

The largest peak in the final difference map is located adjacent to C105 but appears to have no chemical significance. Subsequent peaks are located between or adjacent to atoms already located or in the vicinity of methyl Hs.

Structure description top

(+)-Hexacyclinol is a natural product that was first isolated and characterized by Schlegel et al. (2002). Rychnovsky (2006) proposed the illustrated structure by re-evaluation of the derived 13C NMR spectral data. This structure was confirmed through the synthesis and X-ray analysis of racemic material (Porco et al., 2006). Like others (Mehta & Roy, 2008), we have recently completed a synthesis of (+)-hexacyclinol, in our case from an enzymatically generated and enantiomerically pure cis-1,2-dihydrocatechol (Pinkerton et al., 2009). We report herein the single-crystal X-ray analysis of this material.

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPII (Johnson, 1976) in TEXSAN (Molecular Structure Corporation, 1997); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top
[Figure 1] Fig. 1. Structure of C23H28O7 molecule one with labelling of selected atoms. Anisotropic displacement ellipsoids display 30% probability levels. Hydrogen atoms are drawn as circles with small radii.
[Figure 2] Fig. 2. Structure of C23H28O7 molecule two with labelling of selected atoms. Anisotropic displacement ellipsoids display 30% probability levels. Hydrogen atoms are drawn as circles with small radii.
[Figure 3] Fig. 3. Structure of C23H28O7 molecule three with labelling of selected atoms. Anisotropic displacement ellipsoids display 30% probability levels. Hydrogen atoms are drawn as circles with small radii.
[Figure 4] Fig. 4. Unit cell packing diagram of C23H28O7 projected down the a axis. Anisotropic displacement ellipsoids display 30% probability levels. The alcohol H atoms are drawn as circles with small radii and the remaining H atoms have been deleted.
(1aS,2aS,3S,5aS,6aS,7R,7aS, 7bS,8R,8aS,10R)-7-hydroxy-3-(1-methoxy-1- methylethyl)-10-(2-methyl-1-propenyl)-1a,5a,6a,7,7a,7b,8,8a-octahydro- 2H-8,2a-(epoxymethano)phenanthro[2,3-b:6,7-b']bisoxirene- 2,5(3H)-dione top
Crystal data top
C23H28O7F(000) = 2664
Mr = 416.47Dx = 1.364 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 119334 reflections
a = 10.8270 (1) Åθ = 2.6–27.5°
b = 20.0530 (2) ŵ = 0.10 mm−1
c = 28.0247 (3) ÅT = 200 K
V = 6084.55 (11) Å3Needle, colourless
Z = 120.42 × 0.18 × 0.15 mm
Data collection top
Nonius KappaCCD
diffractometer		5571 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scans with CCDθmax = 27.5°, θmin = 2.6°
Absorption correction: integration
[via Gaussian method (Coppens, 1970) implemented in maXus (Mackay et al., 2000)]		h = −13→13
Tmin = 0.972, Tmax = 0.994k = −26→26
80486 measured reflectionsl = −25→36
7619 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079 Method = Modified Sheldrick w = 1/[σ2(F2) + (0.03P)2 + 0.0P],
where P = (max(Fo2,0) + 2Fc2)/3
S = 0.83(Δ/σ)max = 0.001
7619 reflectionsΔρmax = 0.54 e Å−3
820 parametersΔρmin = −0.25 e Å−3
0 restraintsAbsolute structure: The enantiomer has been assigned by reference to an unchanging centre of chirality in the starting material.
Crystal data top
C23H28O7V = 6084.55 (11) Å3
Mr = 416.47Z = 12
Orthorhombic, P212121Mo Kα radiation
a = 10.8270 (1) ŵ = 0.10 mm−1
b = 20.0530 (2) ÅT = 200 K
c = 28.0247 (3) Å0.42 × 0.18 × 0.15 mm
Data collection top
Nonius KappaCCD
diffractometer		7619 independent reflections
Absorption correction: integration
[via Gaussian method (Coppens, 1970) implemented in maXus (Mackay et al., 2000)]		5571 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.994Rint = 0.036
80486 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 0.83Δρmax = 0.54 e Å−3
7619 reflectionsΔρmin = −0.25 e Å−3
820 parametersAbsolute structure: The enantiomer has been assigned by reference to an unchanging centre of chirality in the starting material.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3484 (2)0.15601 (11)0.72085 (8)0.0299
C20.27315 (19)0.20115 (12)0.75220 (8)0.0320
C30.27084 (19)0.26780 (12)0.75158 (8)0.0309
C40.1877 (2)0.30240 (13)0.78622 (8)0.0369
C50.2149 (2)0.37427 (13)0.79603 (9)0.0448
C60.3238 (2)0.40522 (13)0.77555 (9)0.0426
C70.4057 (2)0.37003 (11)0.74015 (9)0.0339
C80.34130 (18)0.31058 (11)0.71650 (8)0.0276
C90.43535 (19)0.26764 (10)0.68923 (8)0.0272
C100.48673 (19)0.28963 (11)0.64103 (8)0.0309
C110.3911 (2)0.29732 (12)0.60224 (9)0.0358
C120.2960 (2)0.24587 (12)0.60020 (9)0.0370
C130.29373 (19)0.19483 (12)0.63865 (8)0.0309
C140.39485 (19)0.19549 (11)0.67712 (8)0.0281
C150.51777 (19)0.17370 (11)0.65151 (8)0.0309
O160.55958 (14)0.23319 (7)0.62627 (6)0.0337
C170.5156 (2)0.11678 (12)0.61741 (8)0.0357
C180.6034 (2)0.07004 (13)0.61481 (9)0.0412
C190.7156 (2)0.06746 (14)0.64595 (10)0.0504
C200.5942 (3)0.01329 (15)0.57995 (12)0.0664
O210.21643 (15)0.15080 (9)0.63683 (7)0.0481
O220.26572 (15)0.31279 (9)0.61589 (6)0.0419
C230.4397 (2)0.11377 (11)0.75171 (8)0.0347
C240.5434 (2)0.15375 (12)0.77433 (9)0.0418
C250.3664 (3)0.07883 (13)0.79109 (9)0.0466
O260.49970 (15)0.06476 (8)0.72235 (6)0.0393
C270.4243 (3)0.01340 (12)0.70271 (10)0.0493
O280.10381 (16)0.27442 (10)0.80699 (6)0.0515
O290.32731 (18)0.38064 (10)0.82386 (6)0.0555
O300.43866 (17)0.41634 (9)0.70388 (7)0.0461
C1010.8589 (2)0.42906 (12)0.60656 (8)0.0341
C1020.7833 (2)0.38365 (12)0.57556 (9)0.0353
C1030.7806 (2)0.31715 (12)0.57742 (8)0.0337
C1040.6989 (2)0.28108 (13)0.54294 (9)0.0397
C1050.7219 (2)0.20815 (13)0.53624 (9)0.0447
C1060.8344 (2)0.17845 (14)0.55588 (9)0.0475
C1070.9195 (2)0.21771 (12)0.58843 (9)0.0393
C1080.8517 (2)0.27511 (12)0.61317 (8)0.0320
C1090.9392 (2)0.31835 (11)0.64262 (8)0.0333
C1100.9816 (2)0.29827 (12)0.69246 (8)0.0349
C1110.8784 (2)0.28925 (13)0.72856 (9)0.0397
C1120.7785 (2)0.33811 (13)0.72586 (9)0.0384
C1130.7795 (2)0.38726 (12)0.68501 (9)0.0336
C1140.89379 (19)0.39013 (11)0.65232 (8)0.0317
C1151.0048 (2)0.41569 (12)0.68319 (9)0.0353
O1161.04747 (14)0.35658 (8)0.70936 (6)0.0385
C1170.9802 (2)0.47235 (11)0.71650 (8)0.0354
C1181.0530 (2)0.52478 (13)0.72361 (9)0.0421
C1191.1778 (2)0.53375 (14)0.70100 (11)0.0518
C1201.0139 (3)0.58253 (13)0.75441 (10)0.0538
O1210.69216 (14)0.42477 (8)0.68032 (6)0.0430
O1220.75780 (15)0.27021 (9)0.71160 (6)0.0420
C1230.9601 (2)0.46485 (13)0.57641 (9)0.0413
C1241.0661 (2)0.42028 (14)0.56013 (10)0.0518
C1250.8989 (2)0.49591 (14)0.53231 (10)0.0501
O1261.01865 (15)0.51608 (9)0.60449 (7)0.0487
C1270.9463 (3)0.57282 (13)0.61580 (12)0.0642
O1280.61975 (17)0.30835 (9)0.51944 (7)0.0567
O1290.83095 (19)0.19847 (11)0.50687 (7)0.0645
O1300.96384 (17)0.17434 (10)0.62467 (8)0.0522
C2010.38514 (18)0.59697 (10)0.53867 (8)0.0272
C2020.31476 (19)0.63543 (11)0.57649 (8)0.0306
C2030.31062 (18)0.70143 (11)0.58224 (8)0.0289
C2040.2323 (2)0.72855 (12)0.62163 (8)0.0340
C2050.2576 (2)0.79795 (12)0.63791 (9)0.0381
C2060.3626 (2)0.83442 (13)0.61786 (9)0.0408
C2070.4391 (2)0.80679 (11)0.57711 (9)0.0350
C2080.37384 (19)0.75120 (10)0.54964 (8)0.0285
C2090.46373 (19)0.71508 (10)0.51667 (8)0.0284
C2100.5095 (2)0.74653 (11)0.46994 (8)0.0331
C2110.4117 (2)0.75913 (12)0.43313 (9)0.0387
C2120.3113 (2)0.71052 (12)0.42960 (9)0.0365
C2130.3068 (2)0.65565 (11)0.46596 (8)0.0299
C2140.42090 (19)0.64566 (10)0.49810 (8)0.0263
C2150.53408 (19)0.62933 (11)0.46475 (8)0.0300
O2160.58483 (13)0.69366 (7)0.45007 (6)0.0342
C2170.5121 (2)0.58804 (11)0.42100 (8)0.0330
C2180.5857 (2)0.54003 (12)0.40475 (9)0.0361
C2190.7006 (2)0.51586 (14)0.42860 (10)0.0494
C2200.5579 (3)0.50506 (13)0.35848 (9)0.0530
O2210.21737 (14)0.61965 (8)0.46774 (6)0.0431
O2220.28873 (15)0.77640 (8)0.44880 (6)0.0423
C2230.4851 (2)0.55123 (11)0.56191 (8)0.0312
C2240.5945 (2)0.58940 (12)0.58251 (9)0.0363
C2250.4271 (2)0.50934 (13)0.60141 (9)0.0441
O2260.53916 (14)0.50852 (7)0.52626 (6)0.0361
C2270.4617 (3)0.45880 (12)0.50607 (10)0.0473
O2280.15206 (15)0.69639 (9)0.64143 (7)0.0491
O2290.37478 (17)0.80146 (10)0.66304 (6)0.0531
O2300.46259 (17)0.85956 (8)0.54406 (7)0.0469
H110.28800.12280.70870.0348*
H210.22030.17990.77550.0378*
H510.14580.40070.81050.0531*
H610.32500.45370.77280.0501*
H710.48210.35470.75580.0417*
H810.28170.32960.69340.0346*
H910.50890.26450.70970.0320*
H1010.53820.33060.64380.0365*
H1110.42150.31710.57230.0420*
H1210.25990.23300.56940.0445*
H1510.58200.16410.67720.0352*
H1710.44500.11520.59430.0429*
H1910.78700.05980.62700.0764*
H1920.71020.02970.66620.0770*
H1930.72420.10690.66520.0777*
H2010.5970−0.02860.59770.1002*
H2020.51650.01640.56260.0998*
H2030.66310.01370.55830.0997*
H2410.58630.12540.79580.0622*
H2420.50760.19220.79120.0625*
H2430.60070.16980.75050.0621*
H2510.41420.04280.80560.0685*
H2520.34200.11190.81480.0695*
H2530.28940.05870.77840.0695*
H2710.4714−0.01490.68170.0740*
H2720.3852−0.01510.72640.0738*
H2730.35860.03260.68320.0732*
H3010.522 (3)0.4171 (15)0.6991 (11)0.0694*
H10110.80370.46470.61730.0397*
H10210.73360.40380.55290.0415*
H10510.66310.18070.51530.0525*
H10610.83550.12860.56020.0555*
H10710.98600.23520.56840.0469*
H10810.78790.25550.63520.0376*
H10911.01320.32390.62420.0399*
H11011.03720.26090.69300.0400*
H11110.90160.27040.75960.0469*
H11210.73250.35140.75430.0453*
H11511.07020.42720.66050.0407*
H11710.90620.47090.73360.0432*
H11911.17760.57170.68020.0777*
H11921.23740.54150.72420.0772*
H11931.20210.49570.68290.0777*
H12011.07010.59170.78020.0794*
H12020.93080.57660.76740.0800*
H12031.01230.62270.73680.0803*
H12411.12130.44450.53850.0778*
H12421.11250.40630.58870.0768*
H12431.03370.38000.54510.0780*
H12510.95540.53080.52020.0747*
H12520.81860.51710.54080.0741*
H12530.88730.46170.50910.0757*
H12710.99860.60340.63330.0955*
H12720.88110.55920.63870.0951*
H12730.91550.59360.58780.0954*
H13011.036 (3)0.1665 (17)0.6191 (12)0.0785*
H20110.32570.56490.52600.0323*
H20210.27130.61040.59860.0374*
H20510.18850.82260.65640.0451*
H20610.35970.88220.61860.0488*
H20710.51440.78940.59050.0410*
H20810.30920.77430.53070.0334*
H20910.53820.70740.53530.0314*
H21010.55980.78620.47500.0376*
H21110.43560.78140.40420.0460*
H21210.27500.70130.39830.0434*
H21510.59750.60770.48440.0347*
H21710.44290.59920.40280.0392*
H21910.76830.51190.40540.0743*
H21920.72400.54500.45260.0746*
H21930.68400.47330.44260.0751*
H22010.55140.45800.36370.0806*
H22020.62480.51360.33750.0796*
H22030.47980.52270.34390.0796*
H22410.64820.55870.60040.0529*
H22420.56710.62260.60470.0532*
H22430.64140.60840.55770.0540*
H22510.48420.47420.60930.0650*
H22520.41510.53600.62980.0648*
H22530.34990.48830.59280.0657*
H22710.51060.43150.48430.0713*
H22720.42690.43100.53010.0711*
H22730.39440.47850.48810.0715*
H23010.528 (3)0.8734 (16)0.5468 (12)0.0706*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0311 (11)0.0282 (12)0.0303 (12)−0.0040 (10)−0.0020 (10)0.0032 (10)
C20.0276 (11)0.0381 (13)0.0302 (12)−0.0046 (11)0.0006 (10)0.0064 (11)
C30.0274 (11)0.0375 (13)0.0277 (12)−0.0009 (10)−0.0022 (9)0.0006 (11)
C40.0325 (12)0.0472 (15)0.0310 (13)0.0042 (12)0.0020 (11)0.0011 (12)
C50.0453 (14)0.0513 (16)0.0377 (14)0.0101 (13)0.0035 (12)−0.0072 (13)
C60.0475 (14)0.0372 (14)0.0430 (15)0.0054 (12)−0.0030 (12)−0.0067 (12)
C70.0276 (11)0.0317 (13)0.0422 (14)0.0014 (10)−0.0028 (10)−0.0015 (11)
C80.0233 (10)0.0290 (12)0.0307 (12)0.0011 (9)−0.0020 (9)−0.0003 (10)
C90.0233 (10)0.0268 (11)0.0316 (12)0.0001 (9)−0.0017 (9)0.0033 (10)
C100.0278 (11)0.0290 (12)0.0359 (13)0.0002 (10)0.0035 (10)0.0033 (10)
C110.0375 (13)0.0358 (13)0.0340 (13)0.0059 (12)0.0036 (10)0.0065 (11)
C120.0370 (13)0.0434 (15)0.0308 (13)0.0059 (12)−0.0055 (11)0.0023 (11)
C130.0255 (11)0.0345 (13)0.0328 (13)0.0022 (11)−0.0009 (10)−0.0023 (11)
C140.0242 (10)0.0297 (12)0.0305 (12)0.0026 (10)−0.0016 (9)0.0014 (10)
C150.0274 (11)0.0313 (12)0.0339 (13)0.0030 (10)0.0007 (10)0.0017 (10)
O160.0312 (8)0.0304 (8)0.0395 (9)0.0032 (7)0.0061 (7)0.0005 (7)
C170.0344 (12)0.0382 (13)0.0344 (13)0.0009 (12)−0.0013 (10)−0.0035 (11)
C180.0430 (14)0.0389 (14)0.0417 (15)0.0037 (12)0.0038 (12)−0.0015 (12)
C190.0373 (13)0.0491 (16)0.0649 (19)0.0092 (13)0.0010 (13)0.0056 (15)
C200.073 (2)0.0555 (18)0.071 (2)0.0082 (17)0.0045 (18)−0.0242 (17)
O210.0370 (9)0.0545 (11)0.0527 (11)−0.0122 (9)−0.0152 (9)0.0109 (9)
O220.0378 (9)0.0463 (10)0.0415 (10)0.0118 (8)−0.0044 (8)0.0052 (9)
C230.0401 (13)0.0290 (12)0.0352 (13)0.0008 (11)−0.0051 (11)0.0039 (11)
C240.0436 (14)0.0420 (14)0.0396 (14)0.0014 (12)−0.0144 (12)0.0041 (12)
C250.0571 (16)0.0446 (15)0.0379 (14)−0.0045 (14)−0.0054 (13)0.0147 (13)
O260.0440 (9)0.0302 (8)0.0436 (10)0.0025 (8)−0.0081 (8)−0.0002 (8)
C270.0615 (17)0.0313 (13)0.0550 (17)−0.0031 (13)−0.0066 (15)0.0010 (13)
O280.0450 (10)0.0645 (12)0.0449 (11)−0.0010 (10)0.0159 (9)0.0023 (10)
O290.0655 (12)0.0638 (12)0.0371 (10)−0.0013 (11)−0.0084 (9)−0.0092 (10)
O300.0416 (9)0.0315 (9)0.0652 (12)−0.0020 (8)0.0120 (9)0.0047 (9)
C1010.0273 (11)0.0353 (13)0.0396 (13)0.0034 (11)−0.0012 (10)0.0088 (11)
C1020.0275 (11)0.0415 (14)0.0369 (13)0.0057 (11)−0.0032 (11)0.0077 (11)
C1030.0279 (11)0.0387 (14)0.0347 (13)0.0056 (11)0.0016 (10)0.0014 (11)
C1040.0372 (13)0.0483 (15)0.0336 (13)0.0042 (12)0.0012 (11)0.0003 (12)
C1050.0530 (15)0.0518 (16)0.0294 (13)0.0066 (14)0.0030 (12)−0.0071 (12)
C1060.0601 (17)0.0464 (15)0.0360 (15)0.0115 (14)0.0040 (13)−0.0036 (13)
C1070.0330 (12)0.0367 (14)0.0484 (15)0.0063 (11)0.0059 (11)0.0065 (12)
C1080.0253 (11)0.0383 (13)0.0322 (12)0.0021 (10)0.0031 (10)0.0046 (11)
C1090.0241 (11)0.0344 (13)0.0414 (14)0.0046 (10)0.0037 (10)0.0074 (11)
C1100.0281 (11)0.0352 (13)0.0414 (14)0.0000 (11)−0.0030 (10)0.0094 (11)
C1110.0348 (12)0.0458 (15)0.0385 (14)−0.0063 (12)−0.0044 (11)0.0080 (12)
C1120.0294 (12)0.0486 (15)0.0372 (14)−0.0045 (12)0.0034 (11)0.0051 (12)
C1130.0245 (11)0.0371 (13)0.0394 (14)−0.0051 (11)−0.0016 (10)−0.0044 (11)
C1140.0230 (10)0.0359 (13)0.0362 (13)0.0000 (10)0.0012 (10)0.0052 (11)
C1150.0255 (11)0.0390 (13)0.0413 (14)−0.0020 (10)−0.0016 (10)0.0124 (12)
O1160.0297 (8)0.0380 (9)0.0477 (10)−0.0018 (8)−0.0077 (8)0.0104 (8)
C1170.0277 (11)0.0394 (13)0.0392 (13)−0.0048 (11)−0.0015 (10)0.0068 (11)
C1180.0395 (13)0.0438 (15)0.0430 (15)−0.0031 (12)−0.0103 (12)0.0125 (12)
C1190.0365 (13)0.0523 (17)0.0665 (18)−0.0162 (13)−0.0050 (13)0.0141 (15)
C1200.0595 (17)0.0493 (16)0.0526 (17)−0.0082 (15)−0.0133 (14)0.0003 (15)
O1210.0296 (8)0.0420 (10)0.0574 (11)0.0039 (8)0.0073 (8)0.0030 (9)
O1220.0346 (9)0.0464 (10)0.0451 (10)−0.0110 (8)−0.0007 (8)0.0090 (9)
C1230.0344 (13)0.0455 (14)0.0442 (15)−0.0006 (12)−0.0005 (12)0.0139 (13)
C1240.0373 (13)0.0645 (18)0.0535 (17)0.0077 (14)0.0114 (13)0.0243 (15)
C1250.0512 (15)0.0552 (17)0.0440 (16)0.0020 (14)−0.0010 (13)0.0170 (14)
O1260.0364 (9)0.0465 (11)0.0632 (12)−0.0055 (9)−0.0062 (9)0.0198 (10)
C1270.0651 (19)0.0366 (15)0.091 (2)−0.0033 (15)−0.0300 (18)0.0114 (16)
O1280.0539 (11)0.0556 (12)0.0606 (12)0.0102 (10)−0.0246 (10)−0.0048 (10)
O1290.0732 (13)0.0809 (15)0.0394 (11)0.0235 (12)0.0124 (10)−0.0015 (11)
O1300.0435 (10)0.0446 (10)0.0684 (13)0.0108 (10)−0.0083 (10)0.0098 (10)
C2010.0242 (10)0.0241 (11)0.0332 (12)−0.0036 (9)−0.0032 (9)−0.0011 (10)
C2020.0258 (11)0.0342 (13)0.0317 (12)−0.0042 (10)0.0007 (10)0.0054 (10)
C2030.0221 (10)0.0327 (12)0.0319 (12)−0.0009 (10)−0.0013 (9)−0.0003 (10)
C2040.0311 (12)0.0380 (13)0.0328 (13)0.0021 (11)0.0003 (10)0.0021 (11)
C2050.0386 (13)0.0409 (14)0.0347 (14)0.0019 (12)−0.0002 (11)−0.0060 (12)
C2060.0467 (14)0.0327 (13)0.0430 (15)0.0012 (12)−0.0009 (12)−0.0077 (12)
C2070.0309 (11)0.0284 (12)0.0456 (15)−0.0010 (10)−0.0011 (11)−0.0011 (11)
C2080.0244 (11)0.0275 (12)0.0338 (13)−0.0012 (9)0.0020 (9)−0.0006 (10)
C2090.0250 (10)0.0260 (11)0.0342 (12)−0.0006 (10)0.0006 (9)−0.0002 (10)
C2100.0343 (12)0.0253 (11)0.0397 (13)0.0011 (10)0.0067 (11)0.0008 (10)
C2110.0414 (13)0.0350 (13)0.0398 (14)0.0091 (11)0.0107 (11)0.0098 (12)
C2120.0357 (12)0.0403 (14)0.0334 (13)0.0119 (12)−0.0019 (11)0.0038 (11)
C2130.0290 (11)0.0300 (12)0.0306 (12)0.0046 (10)−0.0009 (10)−0.0051 (10)
C2140.0249 (10)0.0250 (11)0.0290 (12)0.0020 (9)−0.0023 (9)0.0000 (10)
C2150.0267 (11)0.0292 (11)0.0343 (13)0.0038 (10)0.0001 (10)0.0052 (10)
O2160.0308 (8)0.0306 (8)0.0412 (9)0.0021 (7)0.0081 (7)0.0003 (8)
C2170.0337 (12)0.0356 (12)0.0297 (12)0.0064 (11)−0.0020 (10)0.0005 (11)
C2180.0400 (13)0.0301 (12)0.0381 (14)0.0033 (11)0.0010 (11)−0.0009 (11)
C2190.0480 (15)0.0493 (16)0.0510 (16)0.0171 (13)0.0014 (13)−0.0034 (14)
C2200.0627 (17)0.0482 (16)0.0482 (17)0.0133 (15)−0.0033 (14)−0.0098 (14)
O2210.0321 (8)0.0418 (10)0.0555 (11)−0.0053 (8)−0.0143 (8)0.0037 (9)
O2220.0413 (9)0.0389 (10)0.0468 (10)0.0157 (8)0.0021 (8)0.0068 (8)
C2230.0354 (12)0.0277 (11)0.0305 (12)0.0012 (10)−0.0036 (10)0.0003 (10)
C2240.0330 (12)0.0423 (14)0.0335 (13)0.0016 (11)−0.0063 (10)0.0022 (12)
C2250.0475 (15)0.0401 (14)0.0448 (15)0.0033 (13)−0.0011 (12)0.0123 (13)
O2260.0368 (9)0.0287 (8)0.0430 (10)0.0048 (8)−0.0024 (8)−0.0024 (7)
C2270.0568 (16)0.0286 (12)0.0566 (17)−0.0002 (13)−0.0030 (14)−0.0064 (12)
O2280.0428 (10)0.0464 (10)0.0579 (12)−0.0045 (9)0.0213 (9)0.0010 (9)
O2290.0563 (11)0.0636 (12)0.0394 (10)−0.0075 (11)−0.0102 (9)−0.0074 (10)
O2300.0436 (10)0.0302 (9)0.0669 (13)−0.0077 (8)0.0111 (10)−0.0002 (9)
Geometric parameters (Å, º) top
C1—C21.502 (3)C112—H11210.978
C1—C141.543 (3)C113—C1141.541 (3)
C1—C231.563 (3)C113—O1211.215 (3)
C1—H110.994C114—C1151.567 (3)
C2—C31.337 (3)C115—O1161.468 (3)
C2—H210.968C115—C1171.494 (3)
C3—C41.495 (3)C115—H11510.979
C3—C81.511 (3)C117—C1181.329 (3)
C4—C51.496 (4)C117—H11710.935
C4—O281.216 (3)C118—C1191.503 (3)
C5—C61.452 (4)C118—C1201.505 (4)
C5—O291.451 (3)C119—H11910.959
C5—H511.002C119—H11920.930
C6—C71.506 (3)C119—H11930.954
C6—O291.441 (3)C120—H12010.961
C6—H610.975C120—H12020.979
C7—C81.532 (3)C120—H12030.946
C7—O301.422 (3)C123—C1241.525 (3)
C7—H710.986C123—C1251.534 (3)
C8—C91.537 (3)C123—O1261.441 (3)
C8—H810.989C124—H12410.979
C9—C101.526 (3)C124—H12420.985
C9—C141.550 (3)C124—H12430.976
C9—H910.984C125—H12510.990
C10—C111.509 (3)C125—H12520.998
C10—O161.440 (3)C125—H12530.954
C10—H1010.995O126—C1271.417 (3)
C11—C121.458 (3)C127—H12710.968
C11—O221.444 (3)C127—H12720.993
C11—H1110.985C127—H12730.950
C12—C131.486 (3)O130—H13010.81 (3)
C12—O221.450 (3)C201—C2021.516 (3)
C12—H1210.983C201—C2141.548 (3)
C13—C141.536 (3)C201—C2231.561 (3)
C13—O211.218 (3)C201—H20110.977
C14—C151.574 (3)C202—C2031.334 (3)
C15—O161.459 (3)C202—H20210.926
C15—C171.489 (3)C203—C2041.494 (3)
C15—H1511.019C203—C2081.516 (3)
C17—C181.337 (3)C204—C2051.490 (3)
C17—H1711.003C204—O2281.216 (3)
C18—C191.496 (3)C205—C2061.464 (3)
C18—C201.503 (4)C205—O2291.453 (3)
C19—H1910.951C205—H20511.035
C19—H1920.948C206—C2071.516 (3)
C19—H1930.962C206—O2291.434 (3)
C20—H2010.976C206—H20610.958
C20—H2020.974C207—C2081.528 (3)
C20—H2030.961C207—O2301.429 (3)
C23—C241.518 (3)C207—H20710.962
C23—C251.529 (3)C208—C2091.525 (3)
C23—O261.437 (3)C208—H20810.993
C24—H2410.951C209—C2101.536 (3)
C24—H2420.984C209—C2141.557 (3)
C24—H2430.968C209—H20910.973
C25—H2510.977C210—C2111.500 (3)
C25—H2520.976C210—O2161.449 (3)
C25—H2530.992C210—H21010.974
O26—C271.425 (3)C211—C2121.464 (3)
C27—H2710.964C211—O2221.444 (3)
C27—H2720.974C211—H21110.962
C27—H2730.977C212—C2131.501 (3)
O30—H3010.91 (3)C212—O2221.447 (3)
C101—C1021.501 (3)C212—H21210.978
C101—C1141.548 (3)C213—C2141.542 (3)
C101—C1231.559 (3)C213—O2211.209 (3)
C101—H10110.979C214—C2151.575 (3)
C102—C1031.335 (3)C215—O2161.461 (3)
C102—H10210.925C215—C2171.499 (3)
C103—C1041.496 (3)C215—H21510.981
C103—C1081.519 (3)C217—C2181.330 (3)
C104—C1051.495 (4)C217—H21710.934
C104—O1281.212 (3)C218—C2191.494 (3)
C105—C1061.464 (4)C218—C2201.504 (3)
C105—O1291.452 (3)C219—H21910.982
C105—H10511.025C219—H21920.927
C106—C1071.517 (4)C219—H21930.956
C106—O1291.431 (3)C220—H22010.957
C106—H10611.006C220—H22020.948
C107—C1081.531 (3)C220—H22031.004
C107—O1301.421 (3)C223—C2241.523 (3)
C107—H10710.979C223—C2251.525 (3)
C108—C1091.526 (3)C223—O2261.440 (3)
C108—H10811.006C224—H22410.984
C109—C1101.525 (3)C224—H22420.959
C109—C1141.545 (3)C224—H22430.941
C109—H10910.959C225—H22510.963
C110—C1111.518 (3)C225—H22520.968
C110—O1161.449 (3)C225—H22530.966
C110—H11010.960O226—C2271.420 (3)
C111—C1121.461 (3)C227—H22710.976
C111—O1221.441 (3)C227—H22720.953
C111—H11110.980C227—H22730.970
C112—C1131.511 (3)O230—H23010.76 (3)
C112—O1221.437 (3)
O16···C1042.941 (3)O128···C2273.489 (3)
O16···C1053.115 (3)O129···C11vii3.128 (3)
O16···C1033.230 (3)O129···C12vii3.224 (3)
O16···C1083.293 (3)O129···C227vii3.476 (3)
O16···O1223.298 (2)O130···C193.489 (3)
O16···O1283.415 (2)O216···C204viii3.003 (3)
O21···O130i2.796 (2)O216···C205viii3.099 (3)
O21···C220ii3.568 (3)O216···C208viii3.319 (2)
O22···C124i3.429 (3)O216···C203viii3.350 (2)
O22···O129ii3.519 (3)O216···O228viii3.459 (2)
O28···O116i3.251 (2)O221···O230ix2.809 (2)
O28···C111i3.298 (3)O221···C20ii3.267 (4)
O28···O228iii3.495 (2)O221···C207ix3.582 (3)
O28···C110i3.504 (3)O222···C224ix3.526 (3)
O28···C212iv3.570 (3)O228···C127i3.409 (3)
O30···O1212.828 (2)O228···C211ix3.455 (3)
O30···C2253.426 (3)O229···C24v3.555 (3)
O30···C27v3.584 (3)O230···C20x3.542 (4)
O116···C4vi2.851 (3)C3···C110i3.595 (3)
O116···C5vi3.052 (3)C4···C110i3.448 (3)
O116···C3vi3.228 (3)C6···C27v3.538 (4)
O116···C8vi3.318 (2)C10···C1043.586 (3)
O121···C25v3.254 (3)C25···C224xi3.574 (4)
O122···C93.547 (3)C106···C227vii3.534 (4)
O122···C103.560 (3)C120···C220xii3.492 (4)
O128···O129ii3.216 (3)C204···C210ix3.557 (3)
O128···C113.400 (3)
C2—C1—C14109.40 (18)C112—C113—C114118.72 (19)
C2—C1—C23110.25 (18)C112—C113—O121118.7 (2)
C14—C1—C23120.75 (18)C114—C113—O121122.5 (2)
C2—C1—H11104.4C113—C114—C109108.99 (18)
C14—C1—H11106.6C113—C114—C101108.40 (17)
C23—C1—H11104.1C109—C114—C101113.7 (2)
C1—C2—C3127.2 (2)C113—C114—C115107.46 (18)
C1—C2—H21116.8C109—C114—C11599.08 (17)
C3—C2—H21115.9C101—C114—C115118.65 (18)
C2—C3—C4117.8 (2)C114—C115—O116104.66 (17)
C2—C3—C8124.5 (2)C114—C115—C117117.19 (19)
C4—C3—C8117.6 (2)O116—C115—C117110.96 (19)
C3—C4—C5116.6 (2)C114—C115—H1151105.9
C3—C4—O28123.1 (2)O116—C115—H1151106.6
C5—C4—O28120.2 (2)C117—C115—H1151110.8
C4—C5—C6119.9 (2)C115—O116—C110109.47 (15)
C4—C5—O29110.4 (2)C115—C117—C118126.1 (2)
C6—C5—O2959.53 (16)C115—C117—H1171116.8
C4—C5—H51115.9C118—C117—H1171117.1
C6—C5—H51122.7C117—C118—C119124.4 (3)
O29—C5—H51111.3C117—C118—C120121.9 (2)
C5—C6—C7122.6 (2)C119—C118—C120113.7 (2)
C5—C6—O2960.23 (16)C118—C119—H1191110.4
C7—C6—O29116.3 (2)C118—C119—H1192110.4
C5—C6—H61117.9H1191—C119—H1192107.2
C7—C6—H61114.0C118—C119—H1193112.1
O29—C6—H61114.5H1191—C119—H1193108.1
C6—C7—C8112.45 (19)H1192—C119—H1193108.3
C6—C7—O30108.22 (19)C118—C120—H1201113.5
C8—C7—O30108.25 (19)C118—C120—H1202112.3
C6—C7—H71110.2H1201—C120—H1202109.0
C8—C7—H71109.4C118—C120—H1203111.2
O30—C7—H71108.2H1201—C120—H1203104.0
C7—C8—C3112.96 (19)H1202—C120—H1203106.3
C7—C8—C9110.47 (17)C111—O122—C11261.03 (15)
C3—C8—C9109.87 (18)C101—C123—C124114.9 (2)
C7—C8—H81106.3C101—C123—C125108.69 (19)
C3—C8—H81108.3C124—C123—C125108.8 (2)
C9—C8—H81108.8C101—C123—O126110.0 (2)
C8—C9—C10121.32 (18)C124—C123—O126104.5 (2)
C8—C9—C14116.39 (17)C125—C123—O126109.9 (2)
C10—C9—C14100.32 (17)C123—C124—H1241110.7
C8—C9—H91106.4C123—C124—H1242107.9
C10—C9—H91103.8H1241—C124—H1242109.4
C14—C9—H91107.3C123—C124—H1243110.0
C9—C10—C11114.65 (18)H1241—C124—H1243111.3
C9—C10—O16103.11 (17)H1242—C124—H1243107.4
C11—C10—O16104.41 (18)C123—C125—H1251107.3
C9—C10—H101111.9C123—C125—H1252111.0
C11—C10—H101110.9H1251—C125—H1252108.6
O16—C10—H101111.4C123—C125—H1253108.3
C10—C11—C12116.1 (2)H1251—C125—H1253110.9
C10—C11—O22118.42 (19)H1252—C125—H1253110.7
C12—C11—O2259.93 (14)C123—O126—C127116.83 (19)
C10—C11—H111115.2O126—C127—H1271107.4
C12—C11—H111119.2O126—C127—H1272108.5
O22—C11—H111117.0H1271—C127—H1272105.2
C11—C12—C13118.1 (2)O126—C127—H1273111.2
C11—C12—O2259.54 (15)H1271—C127—H1273110.3
C13—C12—O22114.42 (19)H1272—C127—H1273114.0
C11—C12—H121120.1C105—O129—C10661.00 (16)
C13—C12—H121116.8C107—O130—H1301108 (2)
O22—C12—H121114.7C202—C201—C214108.56 (17)
C12—C13—C14119.39 (19)C202—C201—C223110.84 (18)
C12—C13—O21118.7 (2)C214—C201—C223120.23 (17)
C14—C13—O21121.7 (2)C202—C201—H2011105.0
C1—C14—C13108.69 (17)C214—C201—H2011108.2
C1—C14—C9113.41 (18)C223—C201—H2011102.8
C13—C14—C9111.30 (18)C201—C202—C203127.3 (2)
C1—C14—C15119.69 (18)C201—C202—H2021116.7
C13—C14—C15106.28 (17)C203—C202—H2021116.0
C9—C14—C1596.88 (16)C202—C203—C204118.0 (2)
C14—C15—O16104.86 (16)C202—C203—C208124.4 (2)
C14—C15—C17119.49 (18)C204—C203—C208117.48 (19)
O16—C15—C17108.69 (18)C203—C204—C205117.5 (2)
C14—C15—H151107.9C203—C204—O228123.3 (2)
O16—C15—H151106.6C205—C204—O228119.1 (2)
C17—C15—H151108.6C204—C205—C206119.4 (2)
C15—O16—C10109.47 (15)C204—C205—O229110.7 (2)
C15—C17—C18124.1 (2)C206—C205—O22958.91 (15)
C15—C17—H171116.8C204—C205—H2051117.8
C18—C17—H171119.0C206—C205—H2051121.0
C17—C18—C19124.7 (2)O229—C205—H2051111.4
C17—C18—C20121.3 (2)C205—C206—C207122.1 (2)
C19—C18—C20114.0 (2)C205—C206—O22960.15 (15)
C18—C19—H191109.9C207—C206—O229116.5 (2)
C18—C19—H192109.1C205—C206—H2061117.8
H191—C19—H192104.7C207—C206—H2061113.5
C18—C19—H193112.2O229—C206—H2061116.5
H191—C19—H193111.5C206—C207—C208113.16 (19)
H192—C19—H193109.2C206—C207—O230108.34 (18)
C18—C20—H201108.6C208—C207—O230107.21 (19)
C18—C20—H202109.5C206—C207—H2071107.5
H201—C20—H202109.6C208—C207—H2071108.9
C18—C20—H203110.6O230—C207—H2071111.7
H201—C20—H203107.8C207—C208—C203112.68 (19)
H202—C20—H203110.7C207—C208—C209110.88 (17)
C12—O22—C1160.52 (15)C203—C208—C209109.91 (17)
C1—C23—C24114.37 (18)C207—C208—H2081104.7
C1—C23—C25108.61 (19)C203—C208—H2081108.1
C24—C23—C25108.9 (2)C209—C208—H2081110.4
C1—C23—O26109.85 (18)C208—C209—C210121.85 (18)
C24—C23—O26105.44 (18)C208—C209—C214115.92 (17)
C25—C23—O26109.54 (19)C210—C209—C214100.26 (17)
C23—C24—H241108.0C208—C209—H2091106.2
C23—C24—H242108.9C210—C209—H2091104.8
H241—C24—H242110.9C214—C209—H2091106.5
C23—C24—H243111.2C209—C210—C211115.33 (19)
H241—C24—H243108.9C209—C210—O216102.06 (16)
H242—C24—H243108.9C211—C210—O216104.85 (19)
C23—C25—H251111.3C209—C210—H2101113.1
C23—C25—H252108.7C211—C210—H2101110.9
H251—C25—H252111.2O216—C210—H2101109.8
C23—C25—H253111.3C210—C211—C212117.3 (2)
H251—C25—H253107.1C210—C211—O222118.8 (2)
H252—C25—H253107.1C212—C211—O22259.70 (15)
C23—O26—C27117.18 (19)C210—C211—H2111117.9
O26—C27—H271111.1C212—C211—H2111116.9
O26—C27—H272114.2O222—C211—H2111113.2
H271—C27—H272107.5C211—C212—C213117.8 (2)
O26—C27—H273110.4C211—C212—O22259.48 (15)
H271—C27—H273105.9C213—C212—O222114.29 (19)
H272—C27—H273107.3C211—C212—H2121119.0
C5—O29—C660.24 (16)C213—C212—H2121117.2
C7—O30—H301111 (2)O222—C212—H2121116.0
C102—C101—C114107.85 (18)C212—C213—C214117.80 (19)
C102—C101—C123110.4 (2)C212—C213—O221119.4 (2)
C114—C101—C123120.67 (18)C214—C213—O221122.7 (2)
C102—C101—H1011106.7C213—C214—C201108.10 (17)
C114—C101—H1011105.2C213—C214—C209108.52 (17)
C123—C101—H1011105.1C201—C214—C209113.13 (17)
C101—C102—C103126.6 (2)C213—C214—C215107.67 (17)
C101—C102—H1021116.8C201—C214—C215119.95 (17)
C103—C102—H1021116.7C209—C214—C21598.77 (16)
C102—C103—C104118.1 (2)C214—C215—O216106.02 (16)
C102—C103—C108124.7 (2)C214—C215—C217118.49 (18)
C104—C103—C108117.2 (2)O216—C215—C217108.48 (18)
C103—C104—C105117.1 (2)C214—C215—H2151107.6
C103—C104—O128123.4 (2)O216—C215—H2151106.5
C105—C104—O128119.4 (2)C217—C215—H2151109.1
C104—C105—C106119.3 (2)C215—O216—C210109.04 (15)
C104—C105—O129109.7 (2)C215—C217—C218125.8 (2)
C106—C105—O12958.80 (16)C215—C217—H2171116.2
C104—C105—H1051119.6C218—C217—H2171117.8
C106—C105—H1051120.9C217—C218—C219125.5 (2)
O129—C105—H105196.3C217—C218—C220120.9 (2)
C105—C106—C107121.4 (2)C219—C218—C220113.6 (2)
C105—C106—O12960.20 (16)C218—C219—H2191110.6
C107—C106—O129116.6 (2)C218—C219—H2192110.3
C105—C106—H1061117.3H2191—C219—H2192109.1
C107—C106—H1061115.9C218—C219—H2193108.4
O129—C106—H1061113.2H2191—C219—H2193109.8
C106—C107—C108111.81 (19)H2192—C219—H2193108.5
C106—C107—O130108.5 (2)C218—C220—H2201110.0
C108—C107—O130107.4 (2)C218—C220—H2202107.3
C106—C107—H1071106.7H2201—C220—H2202109.3
C108—C107—H1071110.1C218—C220—H2203110.8
O130—C107—H1071112.4H2201—C220—H2203110.4
C107—C108—C103111.20 (19)H2202—C220—H2203109.1
C107—C108—C109111.98 (18)C212—O222—C21160.82 (14)
C103—C108—C109110.86 (19)C201—C223—C224113.69 (18)
C107—C108—H1081108.2C201—C223—C225109.92 (18)
C103—C108—H1081105.8C224—C223—C225108.77 (19)
C109—C108—H1081108.5C201—C223—O226109.98 (17)
C108—C109—C110122.16 (19)C224—C223—O226104.24 (18)
C108—C109—C114115.27 (18)C225—C223—O226110.09 (18)
C110—C109—C114100.41 (19)C223—C224—H2241109.7
C108—C109—H1091107.1C223—C224—H2242110.7
C110—C109—H1091105.8H2241—C224—H2242106.7
C114—C109—H1091104.6C223—C224—H2243110.1
C109—C110—C111114.85 (18)H2241—C224—H2243108.1
C109—C110—O116103.56 (18)H2242—C224—H2243111.4
C111—C110—O116103.92 (19)C223—C225—H2251107.8
C109—C110—H1101114.2C223—C225—H2252110.4
C111—C110—H1101110.9H2251—C225—H2252107.6
O116—C110—H1101108.4C223—C225—H2253114.6
C110—C111—C112115.5 (2)H2251—C225—H2253107.0
C110—C111—O122118.6 (2)H2252—C225—H2253109.3
C112—C111—O12259.32 (15)C223—O226—C227117.00 (17)
C110—C111—H1111116.6O226—C227—H2271108.8
C112—C111—H1111119.6O226—C227—H2272111.3
O122—C111—H1111115.0H2271—C227—H2272109.2
C111—C112—C113118.1 (2)O226—C227—H2273111.4
C111—C112—O12259.64 (15)H2271—C227—H2273108.1
C113—C112—O122114.1 (2)H2272—C227—H2273108.0
C111—C112—H1121121.2C205—O229—C20660.93 (15)
C113—C112—H1121116.3C207—O230—H2301112 (3)
O122—C112—H1121114.0
O16—C10—C9—C8−174.4 (2)C10—C11—C12—C135.9 (3)
O16—C10—C9—C14−44.6 (2)C11—O22—C12—C13109.4 (2)
O16—C10—C11—O22138.8 (2)C11—C10—O16—C15−98.6 (2)
O16—C10—C11—C1270.5 (2)C11—C10—C9—C1468.3 (2)
O16—C15—C14—C1−158.0 (2)C11—C12—C13—C14−3.5 (3)
O16—C15—C14—C9−36.0 (2)C12—C13—C14—C15−69.6 (2)
O16—C15—C14—C1378.6 (2)C13—C14—C1—C23145.4 (2)
O16—C15—C17—C18100.8 (3)C13—C14—C15—C17−43.5 (3)
O21—C13—C12—O22114.4 (2)C14—C1—C23—C2460.0 (3)
O21—C13—C12—C11−178.5 (2)C14—C1—C23—C25−178.1 (2)
O21—C13—C14—C1−24.9 (3)C14—C15—C17—C18−139.1 (2)
O21—C13—C14—C9−150.5 (2)C15—C14—C1—C2323.2 (3)
O21—C13—C14—C15105.2 (2)C15—C17—C18—C190.7 (4)
O22—C11—C10—C926.8 (3)C15—C17—C18—C20179.0 (2)
O22—C11—C12—C13−103.3 (2)C24—C23—O26—C27170.2 (2)
O22—C12—C11—C10109.2 (2)C25—C23—O26—C2753.2 (3)
O22—C12—C13—C14−70.6 (2)C101—C102—C103—C104−179.7 (2)
O26—C23—C1—C2172.6 (2)C101—C102—C103—C1082.3 (4)
O26—C23—C1—C14−58.3 (3)C101—C114—C109—C108−54.2 (2)
O28—C4—C3—C2−16.9 (3)C101—C114—C109—C110172.5 (2)
O28—C4—C3—C8159.9 (2)C101—C114—C113—C112164.9 (2)
O28—C4—C5—O29106.8 (2)C101—C114—C115—C11780.5 (3)
O28—C4—C5—C6172.6 (2)C101—C123—O126—C127−69.5 (3)
O29—C5—C4—C3−71.1 (3)C102—C101—C114—C10945.0 (2)
O29—C5—C6—C7103.9 (2)C102—C101—C114—C113−76.4 (2)
O29—C6—C5—C4−97.4 (2)C102—C101—C114—C115160.8 (2)
O29—C6—C7—O30−151.7 (2)C102—C101—C123—C124−71.8 (3)
O29—C6—C7—C888.8 (2)C102—C101—C123—C12550.3 (3)
O30—C7—C6—C5138.3 (2)C102—C103—C104—C105163.8 (2)
O30—C7—C8—C3−163.8 (2)C102—C103—C108—C107−132.4 (2)
O30—C7—C8—C972.7 (2)C102—C103—C108—C109−7.2 (3)
O116—C110—C109—C108−172.3 (2)C103—C102—C101—C114−21.2 (3)
O116—C110—C109—C114−43.4 (2)C103—C102—C101—C123112.6 (3)
O116—C110—C111—O122139.9 (2)C103—C104—C105—C106−11.4 (3)
O116—C110—C111—C11272.5 (2)C103—C108—C107—C106−50.5 (3)
O116—C115—C114—C101−156.1 (2)C103—C108—C109—C110154.5 (2)
O116—C115—C114—C109−32.7 (2)C103—C108—C109—C11432.3 (3)
O116—C115—C114—C11380.6 (2)C104—C103—C108—C10749.6 (3)
O116—C115—C117—C118102.7 (3)C104—C103—C108—C109174.8 (2)
O121—C113—C112—O122107.4 (2)C104—C105—O129—C106113.0 (2)
O121—C113—C112—C111174.5 (2)C104—C105—C106—C1078.3 (3)
O121—C113—C114—C101−18.0 (3)C105—O129—C106—C107−112.6 (2)
O121—C113—C114—C109−142.2 (2)C105—C104—C103—C108−18.1 (3)
O121—C113—C114—C115111.3 (2)C105—C106—C107—C10823.3 (3)
O122—C111—C110—C10927.5 (3)C106—C107—C108—C109−175.1 (2)
O122—C111—C112—C113−102.9 (2)C107—C108—C109—C110−80.7 (3)
O122—C112—C111—C110109.5 (2)C107—C108—C109—C114157.1 (2)
O122—C112—C113—C114−75.4 (3)C108—C109—C110—C111−59.7 (3)
O126—C123—C101—C102170.7 (2)C108—C109—C114—C11366.8 (2)
O126—C123—C101—C114−62.4 (3)C108—C109—C114—C115178.9 (2)
O128—C104—C103—C102−13.4 (4)C109—C110—O116—C11523.0 (2)
O128—C104—C103—C108164.7 (2)C109—C110—C111—C112−39.9 (3)
O128—C104—C105—O129101.4 (3)C109—C114—C101—C123−83.1 (3)
O128—C104—C105—C106165.9 (2)C109—C114—C113—C11240.7 (3)
O129—C105—C104—C103−75.9 (3)C109—C114—C115—C117−156.1 (2)
O129—C105—C106—C107104.8 (3)C110—O116—C115—C1146.6 (2)
O129—C106—C105—C104−96.4 (2)C110—O116—C115—C117133.9 (2)
O129—C106—C107—O130−148.7 (2)C110—C109—C114—C113−66.4 (2)
O129—C106—C107—C10893.1 (2)C110—C109—C114—C11545.7 (2)
O130—C107—C106—C105141.5 (2)C110—C111—O122—C112−104.3 (2)
O130—C107—C108—C103−169.4 (2)C110—C111—C112—C1136.6 (3)
O130—C107—C108—C10966.0 (2)C111—O122—C112—C113109.6 (2)
O216—C210—C209—C208−176.8 (2)C111—C110—O116—C115−97.4 (2)
O216—C210—C209—C214−47.3 (2)C111—C110—C109—C11469.2 (2)
O216—C210—C211—O222144.3 (2)C111—C112—C113—C114−8.3 (3)
O216—C210—C211—C21275.7 (2)C112—C113—C114—C115−65.7 (3)
O216—C215—C214—C201−149.8 (2)C113—C114—C101—C123155.6 (2)
O216—C215—C214—C209−26.6 (2)C113—C114—C115—C117−42.7 (3)
O216—C215—C214—C21386.1 (2)C114—C101—C123—C12455.1 (3)
O216—C215—C217—C21899.9 (3)C114—C101—C123—C125177.2 (2)
O221—C213—C212—O222104.0 (2)C114—C115—C117—C118−137.2 (2)
O221—C213—C212—C211171.0 (2)C115—C114—C101—C12332.8 (3)
O221—C213—C214—C201−14.3 (3)C115—C117—C118—C119−3.8 (4)
O221—C213—C214—C209−137.4 (2)C115—C117—C118—C120173.9 (2)
O221—C213—C214—C215116.6 (2)C124—C123—O126—C127166.7 (2)
O222—C211—C210—C20932.9 (3)C125—C123—O126—C12750.1 (3)
O222—C211—C212—C213−103.2 (2)C201—C202—C203—C204178.7 (2)
O222—C212—C211—C210109.1 (2)C201—C202—C203—C2082.6 (3)
O222—C212—C213—C214−78.9 (2)C201—C214—C209—C208−54.8 (2)
O226—C223—C201—C202172.2 (2)C201—C214—C209—C210172.0 (2)
O226—C223—C201—C214−59.8 (2)C201—C214—C213—C212168.7 (2)
O228—C204—C203—C202−17.2 (3)C201—C214—C215—C21788.1 (2)
O228—C204—C203—C208159.2 (2)C201—C223—O226—C227−67.7 (2)
O228—C204—C205—O229108.3 (2)C202—C201—C214—C20940.4 (2)
O228—C204—C205—C206173.4 (2)C202—C201—C214—C213−79.8 (2)
O229—C205—C204—C203−70.0 (3)C202—C201—C214—C215156.3 (2)
O229—C205—C206—C207104.4 (2)C202—C201—C223—C224−71.4 (2)
O229—C206—C205—C204−97.7 (2)C202—C201—C223—C22550.8 (2)
O229—C206—C207—O230−152.9 (2)C202—C203—C204—C205161.0 (2)
O229—C206—C207—C20888.3 (2)C202—C203—C208—C207−136.4 (2)
O230—C207—C206—C205137.2 (2)C202—C203—C208—C209−12.2 (3)
O230—C207—C208—C203−163.3 (2)C203—C202—C201—C214−16.9 (3)
O230—C207—C208—C20973.1 (2)C203—C202—C201—C223117.2 (2)
C1—C2—C3—C4179.7 (2)C203—C204—C205—C206−4.9 (3)
C1—C2—C3—C83.2 (4)C203—C208—C207—C206−43.8 (3)
C1—C14—C9—C8−52.5 (2)C203—C208—C209—C210159.9 (2)
C1—C14—C9—C10174.6 (2)C203—C208—C209—C21437.5 (2)
C1—C14—C13—C12160.3 (2)C204—C203—C208—C20747.5 (2)
C1—C14—C15—C1779.9 (3)C204—C203—C208—C209171.7 (2)
C1—C23—O26—C27−66.1 (2)C204—C205—O229—C206112.7 (2)
C2—C1—C14—C939.3 (2)C204—C205—C206—C2076.6 (3)
C2—C1—C14—C13−85.0 (2)C205—O229—C206—C207−113.4 (2)
C2—C1—C14—C15152.7 (2)C205—C204—C203—C208−22.6 (3)
C2—C1—C23—C24−69.2 (2)C205—C206—C207—C20818.4 (3)
C2—C1—C23—C2552.7 (2)C206—C207—C208—C209−167.5 (2)
C2—C3—C4—C5161.0 (2)C207—C208—C209—C210−74.9 (2)
C2—C3—C8—C7−135.7 (2)C207—C208—C209—C214162.8 (2)
C2—C3—C8—C9−11.9 (3)C208—C209—C210—C211−63.7 (3)
C3—C2—C1—C14−17.0 (3)C208—C209—C214—C21365.2 (2)
C3—C2—C1—C23118.1 (2)C208—C209—C214—C215177.2 (2)
C3—C4—C5—C6−5.3 (3)C209—C210—O216—C21531.0 (2)
C3—C8—C7—C6−44.4 (3)C209—C210—C211—C212−35.7 (3)
C3—C8—C9—C10158.4 (2)C209—C214—C201—C223−88.7 (2)
C3—C8—C9—C1436.0 (2)C209—C214—C213—C21245.7 (3)
C4—C3—C8—C747.8 (3)C209—C214—C215—C217−148.7 (2)
C4—C3—C8—C9171.6 (2)C210—O216—C215—C214−2.3 (2)
C4—C5—O29—C6113.5 (2)C210—O216—C215—C217125.9 (2)
C4—C5—C6—C76.5 (4)C210—C209—C214—C213−68.0 (2)
C5—O29—C6—C7−114.2 (2)C210—C209—C214—C21544.1 (2)
C5—C4—C3—C8−22.2 (3)C210—C211—O222—C212−106.5 (2)
C5—C6—C7—C818.8 (3)C210—C211—C212—C2135.8 (3)
C6—C7—C8—C9−167.9 (2)C211—O222—C212—C213109.2 (2)
C7—C8—C9—C10−76.3 (2)C211—C210—O216—C215−89.6 (2)
C7—C8—C9—C14161.3 (2)C211—C210—C209—C21465.7 (2)
C8—C9—C10—C11−61.5 (3)C211—C212—C213—C214−12.0 (3)
C8—C9—C14—C1370.4 (2)C212—C213—C214—C215−60.3 (2)
C8—C9—C14—C15−179.1 (2)C213—C214—C201—C223151.1 (2)
C9—C10—O16—C1521.5 (2)C213—C214—C215—C217−35.9 (2)
C9—C10—C11—C12−41.6 (3)C214—C201—C223—C22456.6 (3)
C9—C14—C1—C23−90.2 (2)C214—C201—C223—C225178.8 (2)
C9—C14—C13—C1234.7 (3)C214—C215—C217—C218−139.3 (2)
C9—C14—C15—C17−158.1 (2)C215—C214—C201—C22327.3 (3)
C10—O16—C15—C149.9 (2)C215—C217—C218—C2193.5 (4)
C10—O16—C15—C17138.7 (2)C215—C217—C218—C220−175.9 (2)
C10—C9—C14—C13−62.5 (2)C224—C223—O226—C227170.1 (2)
C10—C9—C14—C1548.0 (2)C225—C223—O226—C22753.6 (2)
C10—C11—O22—C12−105.4 (2)
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+1; (iii) −x, y−1/2, −z+3/2; (iv) −x+1/2, −y+1, z+1/2; (v) −x+1, y+1/2, −z+3/2; (vi) x+1, y, z; (vii) x+1/2, −y+1/2, −z+1; (viii) x+1/2, −y+3/2, −z+1; (ix) x−1/2, −y+3/2, −z+1; (x) x, y+1, z; (xi) −x+1, y−1/2, −z+3/2; (xii) −x+3/2, −y+1, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O30—H301···O1210.91 (3)1.92 (3)2.828 (3)172 (3)
O130—H1301···O21vi0.81 (3)2.04 (3)2.796 (3)155 (3)
O230—H2301···O221viii0.76 (3)2.10 (3)2.809 (3)156 (3)
Symmetry codes: (vi) x+1, y, z; (viii) x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formulaC23H28O7
Mr416.47
Crystal system, space groupOrthorhombic, P212121
Temperature (K)200
a, b, c (Å)10.8270 (1), 20.0530 (2), 28.0247 (3)
V (Å3)6084.55 (11)
Z12
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.42 × 0.18 × 0.15
Data collection
DiffractometerNonius KappaCCD
Absorption correctionIntegration
[via Gaussian method (Coppens, 1970) implemented in maXus (Mackay et al., 2000)]
Tmin, Tmax0.972, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections		80486, 7619, 5571
Rint0.036
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.079, 0.83
No. of reflections7619
No. of parameters820
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.54, −0.25
Absolute structureThe enantiomer has been assigned by reference to an unchanging centre of chirality in the starting material.

Computer programs: COLLECT (Nonius, 2001), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), ORTEPII (Johnson, 1976) in TEXSAN (Molecular Structure Corporation, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O30—H301···O1210.91 (3)1.92 (3)2.828 (3)172 (3)
O130—H1301···O21i0.81 (3)2.04 (3)2.796 (3)155 (3)
O230—H2301···O221ii0.76 (3)2.10 (3)2.809 (3)156 (3)
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, −z+1.
 

Acknowledgements

We thank the Australian Research Council for supporting this research. DMP is the grateful recipient of an ANU PhD Scholarship.

References

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ISSN: 2056-9890
Volume 66| Part 2| February 2010| Pages o342-o343
https://doi.org/10.1107/S1600536810000620
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