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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 70| Part 8| August 2014| Page o842
doi:10.1107/S1600536814014998

3β-Hy­droxy-28-norolea-12,17-dien-11-one

Werner Seebacher,a Robert Weis,a Johanna Faist,a Robert Safb and Ferdinand Belajc*

aInstitute of Pharmaceutical Sciences, Department of Pharmaceutical Chemistry, Karl-Franzens University Graz, Schubertstrasse 1, A-8010 Graz, Austria, bInstitute of Chemical Technology of Organic Materials, Erzherzog-Johann University, Stremayrgasse 26/1, A-8010 Graz, Austria, and cInstitute of Chemistry, Karl-Franzens University Graz, Schubertstrasse 1, A-8010 Graz, Austria
*Correspondence e-mail: ferdinand.belaj@uni-graz.at

(Received 19 December 2013; accepted 25 June 2014; online 2 July 2014)

The title compound, C29H44O2, was formed by treatment of 11-oxooleanolic acid under strong alkaline conditions. The absolute structure of the chiral mol­ecules could not be determined reliably from the diffraction data, but is known from other triterpenes. The asymmetric unit consists of two mol­ecules, 1 and 2. In both mol­ecules, rings A and B show chair conformations. The other rings show mixed forms between envelope and half-chair conformations with atoms in positions 8, 15 and 21 forming the flaps in rings C, D and E, respectively. Rings D and E of mol­ecule 2 are disordered over two orientations, with occupancies of 0.557 (4) and 0.443 (4), which differ in the direction of the flap in ring E. In the crystal, mol­ecules 1, as well as the mol­ecules 2, are linked by O—H⋯O hydrogen bonds, forming chains parallel to the b axis.

Keywords: crystal structure.

CCDC reference: 1010257

Related literature

For the synthesis of 11-oxo oleanolic acid, see: Ruzicka et al. (1938[Ruzicka, L., Cohen, S. L., Furter, M. & van der Sluys-Veer, F. C. (1938). Helv. Chim. Acta, 21, 1735-1746.]).

[Scheme 1]

Experimental

Crystal data

  • C29H44O2

  • Mr = 424.64

  • Monoclinic, P 21

  • a = 12.2678 (5) Å

  • b = 16.0544 (6) Å

  • c = 12.9903 (5) Å

  • β = 104.448 (2)°

  • V = 2477.55 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.38 × 0.35 × 0.27 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.538, Tmax = 0.745

  • 15485 measured reflections

  • 5293 independent reflections

  • 4654 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.103

  • S = 1.04

  • 5293 reflections

  • 685 parameters

  • 31 restraints

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

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3⋯O11i 0.84 2.04 (2) 2.792 (2) 148 (4)
O33—H33⋯O41ii 0.84 2.13 (2) 2.921 (2) 158 (4)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+2]; (ii) [-x+1, y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: modified ORTEP (Johnson, 1965[Johnson, C. K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1010257

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814014998/fy2111sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814014998/fy2111Isup2.hkl

checkCIF report


Comment top

Treatment of 11-oxo-oleanolic acid with potassium hydroxide in diethylene glycol at higher temperatures yielded the decarboxylation product 3β-hydroxy-28-norolea-12,17-dien-11-one under formation of a conjugated double bond system. This neutral compound crystallized from hexane in form of prisms. The asymmetric unit consists of two molecules 1 and 2 (Fig. 1). Rings D and E of molecule 2 are disordered over two orientations (Fig. 3). The molecules 1 as well as the molecules 2 are interconnected by hydrogen bonds to form chains parallel to the monoclinic b axis (Table 1).

Related literature top

For the synthesis of 11-oxo oleanolic acid, see: Ruzicka et al. (1938).

Experimental top

Potassium hydroxide (200 mg, 3.56 mmol) was added to 1.4 ml of diethylene glycol and stirred at 100°C. To the brown solution, 11-oxooleanolic acid (480 mg, 1.02 mmol) was added and heated up to 220°C. The reaction mixture was stirred under reflux for 4 h at this temperature. After cooling to room temperature, the reaction mixture was brought to pH = 1 (pH-paper) by addition of water and concentrated HCl. The precipitate was filtered by suction and washed with water. It was dissolved in chloroform and extracted twice with sodium hydroxide solution (2 N) and the organic phase was washed with water, dried over calcium chloride, filtered off and evaporated in vacuo. The residue was purified by use of CC over silica using ether as eluent. The product was recrystallized from hexane to give 180 mg (42%) of pale yellow prisms. Single crystals were obtained by slow evaporation of the solvent. M.p.: 197 – 200°C; Rf = 0.52 (ether). [α]D20 = +188.4°; [α]54620 = +236.4°; (c = 0.154, CH3OH).

IR (KBr): ν = 3477 (m), 2953 (s), 2869 (s), 1648 (s), 1622 (s), 1590 (m), 1457 (w), 1386 (m), 1365 (w), 1323 (w), 1201 (w) cm-1; UV (EtOH): λ (log ε) = 297 (4.817), 206 (4.327) nm.

1H NMR (400 MHz, CDCl3, 24°C, in p.p.m.): δ 0.69 (d, J = 11.7 Hz, 1H, 5-H), 0.78 (s, 3H, 24-H), 0.87 (s, 6H, 29-H, 30-H), 0.91–0.94 (m, 1H, 1-H), 0.97 (s, 3H, 23-H), 1.02 (s, 3H, 26-H), 1.14 (s, 3H, 27-H), 1.15 (s, 3H, 25-H), 1.27–1.78 (m, 11H, 2-H, 6-H, 7-H, 15-H, 19-H, 21-H), 1.94–2.24 (m, 5H, 16-H, 19-H, 22-H), 2.38 (s, 1H, 9-H), 2.76 (dt, J = 13.3, 3.2 Hz, 1H, 1-H), 3.20 (dd, J = 11.0, 5.0 Hz, 1H, 3-H), 5.68 (s, 1H, 12-H).

13C NMR (100 MHz, CDCl3, 24°C, in p.p.m.): δ 15.61 (C-24), 16.81 (C-25), 17.59 (C-6), 18.14 (C-26), 18.46 (C-27), 26.43 (C-15), 27.31 (C-2), 28.03, 28.63 (C-29, C-30), 28.07 (C-23), 28.54 (C-16), 29.23 (C-20), 29.91 (C-22), 33.82 (C-7), 34.57 (C-21), 37.13 (C-10), 38.99 (C-19), 39.08 (C-4), 39.12 (C-1), 42.24 (C-14), 43.64 (C-8), 55.23 (C-5), 60.91 (C-9), 78.76 (C-3), 119.99 (C-12), 125.33 (C-18), 141.64 (C-17), 158.40 (C-13), 200.76 (C-11).

MS (ES+): m/z (%) = 425 [MH+] (100.0), 317 (2.0), 143 (3.9), 130 (10.5), 120 (12.5), 115 (33.6); C29H44O2 (424.67). HRMS (MALDI): calcd. for (C29H45O2) [MH+]: 425.3420; found: 425.3469.

All NMR data were recorded using a Varian UnityInova spectrometer 400 MHz; TMS was used as internal standard. For optical rotation measurements a 241 MC polarimeter (Perkin-Elmer) was used. A Varian MAT 711 mass spectrometer was used with 70 eV electron ionization (EI) and field desorption. HRMS was performed on a Micromass Tofspec. IR spectra were measured with a System 2000 FTIR spectrometer (Perkin-Elmer) and UV-visible spectra with a Lambda 17 spectrophotometer (Perkin-Elmer).

Refinement top

Due to the absence of heavier elements the absolute structure of the chiral molecules could not be determined reliably from the data but is known from other triterpenes. The symmetry-equivalent reflections including 3538 Friedel pairs were averaged.

The asymmetric unit consists of two molecules (1, 2). In molecule 2 rings D and E are disordered over two orientations and were refined with site occupation factors of 0.557 (4) and 0.443 (4), respectively. The same anisotropic displacement parameters were used for three atoms and 'rigid bond' restraints were applied for the atoms of the disordered part. The equivalent bonds in this disordered part were restrained to have the same lengths.

The other non-hydrogen atoms were refined with anisotropic displacement parameters without any constraints.

The O—H distances were fixed to 0.84 Å and the H atoms of the OH groups were refined with a common isotropic displacement parameter without any constraints to the bond angles. The H atoms of the tertiary C—H groups were refined with common isotropic displacement parameters and all X—C—H angles equal at a C—H distance of 1.00 Å. The H atoms of the CH2 groups were refined with common isotropic displacement parameters for the H atoms of the same group (or of the same ring in the disordered part, resp.) and idealized geometry with approximately tetrahedral angles and C—H distances of 0.99 Å. The H atoms at C12 and C42 were put at the external bisector of the C—C—C angle at a C—H distance of 0.95 Å. The H atoms of the methyl groups were refined with common isotropic displacement parameters for the H atoms of the same group (or for all the methyl groups in the disordered part, resp.) and idealized geometries with tetrahedral angles, enabling rotation around the C—C bond, and C—H distances of 0.98 Å.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: modified ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP plot (Johnson, 1965) of the asymmetric unit showing the atomic numbering scheme. The probability ellipsoids are drawn at the 50% probability level. The disordered part is drawn with open bonds for the fragment where the atoms have site occupation factors of 0.443 (4).
[Figure 2] Fig. 2. Stereoscopic ORTEP plot (Johnson, 1965) of molecule 1 showing the atomic numbering scheme. The probability ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. Stereoscopic ORTEP plot (Johnson, 1965) of molecule 2 showing the atomic numbering scheme. The probability ellipsoids are drawn at the 50% probability level. The disordered part is drawn with open bonds for the fragment where the atoms have site occupation factors of 0.443 (4).
3β-Hydroxy-28-norolea-12,17-dien-11-one top
Crystal data top
C29H44O2F(000) = 936
Mr = 424.64Dx = 1.138 Mg m−3
Monoclinic, P21Melting point = 470–473 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 12.2678 (5) ÅCell parameters from 7273 reflections
b = 16.0544 (6) Åθ = 2.5–26.4°
c = 12.9903 (5) ŵ = 0.07 mm−1
β = 104.448 (2)°T = 100 K
V = 2477.55 (17) Å3Block, pale yellow
Z = 40.38 × 0.35 × 0.27 mm
Data collection top
Bruker APEXII CCD
diffractometer		5293 independent reflections
Radiation source: fine-focus sealed tube4654 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ϕ and ω scansθmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2010)		h = −15→15
Tmin = 0.538, Tmax = 0.745k = −19→20
15485 measured reflectionsl = −16→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0597P)2 + 0.4012P]
where P = (Fo2 + 2Fc2)/3
5293 reflections(Δ/σ)max = 0.001
685 parametersΔρmax = 0.22 e Å−3
31 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C29H44O2V = 2477.55 (17) Å3
Mr = 424.64Z = 4
Monoclinic, P21Mo Kα radiation
a = 12.2678 (5) ŵ = 0.07 mm−1
b = 16.0544 (6) ÅT = 100 K
c = 12.9903 (5) Å0.38 × 0.35 × 0.27 mm
β = 104.448 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		5293 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2010)		4654 reflections with I > 2σ(I)
Tmin = 0.538, Tmax = 0.745Rint = 0.031
15485 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03831 restraints
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.22 e Å−3
5293 reflectionsΔρmin = −0.18 e Å−3
685 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.56673 (19)0.70580 (14)0.9397 (2)0.0220 (5)
H110.52120.74380.97220.021 (5)*
H120.53840.70970.86150.021 (5)*
C20.5519 (2)0.61639 (15)0.9748 (2)0.0252 (5)
H210.57420.61351.05340.029 (5)*
H220.47140.60070.95110.029 (5)*
C30.6218 (2)0.55456 (15)0.9297 (2)0.0254 (5)
H310.59220.55340.85070.020 (3)*
O30.61486 (16)0.47186 (12)0.96916 (18)0.0397 (5)
H30.5463 (8)0.460 (2)0.960 (3)0.063 (8)*
C40.74744 (19)0.57634 (14)0.95482 (19)0.0208 (5)
C50.75942 (18)0.66913 (14)0.92399 (18)0.0177 (4)
H50.72600.67150.84550.020 (3)*
C60.88191 (19)0.69683 (15)0.9390 (2)0.0226 (5)
H610.91640.70731.01530.030 (5)*
H620.92530.65220.91470.030 (5)*
C70.88569 (19)0.77608 (14)0.8752 (2)0.0232 (5)
H710.85290.76430.79900.029 (5)*
H720.96520.79240.88360.029 (5)*
C80.82157 (17)0.84966 (14)0.90925 (19)0.0197 (5)
C90.70127 (17)0.81911 (13)0.91449 (18)0.0172 (4)
H90.66110.80870.83860.020 (3)*
C100.69188 (18)0.73431 (14)0.97192 (17)0.0179 (4)
C110.63892 (18)0.89211 (15)0.94712 (18)0.0205 (5)
O110.57411 (14)0.88509 (11)1.00575 (15)0.0282 (4)
C120.65632 (19)0.97442 (14)0.90521 (18)0.0209 (5)
H1210.60891.01850.91630.020 (3)*
C130.73478 (18)0.99204 (14)0.85198 (18)0.0196 (5)
C140.80878 (18)0.92267 (14)0.82496 (19)0.0199 (5)
C150.92351 (19)0.96124 (15)0.8247 (2)0.0259 (5)
H1510.95960.98240.89670.026 (5)*
H1520.97290.91770.80680.026 (5)*
C160.9116 (2)1.03230 (15)0.7450 (2)0.0285 (6)
H1610.98541.06010.75370.036 (6)*
H1620.88881.00950.67200.036 (6)*
C170.8259 (2)1.09517 (15)0.7596 (2)0.0269 (5)
C180.74776 (19)1.07751 (14)0.81372 (19)0.0221 (5)
C190.6686 (2)1.14449 (14)0.8350 (2)0.0246 (5)
H1910.66381.13950.90970.039 (6)*
H1920.59251.13390.78890.039 (6)*
C200.7025 (2)1.23423 (15)0.8162 (2)0.0295 (6)
C210.7361 (2)1.23658 (17)0.7106 (2)0.0355 (6)
H2110.75631.29440.69630.051 (7)*
H2120.67081.21970.65260.051 (7)*
C220.8354 (2)1.17911 (17)0.7106 (2)0.0366 (6)
H2210.84071.17100.63650.048 (6)*
H2220.90571.20640.75040.048 (6)*
C230.8009 (2)0.51984 (15)0.8847 (2)0.0280 (5)
H2310.88300.52510.90680.038 (5)*
H2320.77400.53670.81020.038 (5)*
H2330.77960.46180.89260.038 (5)*
C240.8059 (2)0.55615 (17)1.0711 (2)0.0301 (6)
H2410.81030.49561.08080.038 (5)*
H2420.76260.58021.11780.038 (5)*
H2430.88200.57971.08880.038 (5)*
C250.7305 (2)0.74225 (15)1.09450 (19)0.0255 (5)
H2510.71630.79911.11550.031 (4)*
H2520.81110.73001.11830.031 (4)*
H2530.68840.70271.12720.031 (4)*
C260.8895 (2)0.88082 (16)1.0190 (2)0.0270 (5)
H2610.88830.83831.07290.039 (5)*
H2620.85580.93241.03710.039 (5)*
H2630.96740.89151.01650.039 (5)*
C270.75315 (19)0.89320 (15)0.71071 (19)0.0222 (5)
H2710.68760.85850.71130.030 (4)*
H2720.80750.86060.68340.030 (4)*
H2730.72910.94170.66490.030 (4)*
C290.6023 (2)1.29271 (16)0.8107 (2)0.0344 (6)
H2910.62561.35040.80350.039 (5)*
H2920.57631.28710.87580.039 (5)*
H2930.54101.27800.74920.039 (5)*
C300.8008 (3)1.26177 (18)0.9081 (3)0.0438 (8)
H3010.85981.21910.92090.051 (5)*
H3020.77401.26940.97250.051 (5)*
H3030.83151.31450.88970.051 (5)*
C310.3809 (2)0.97248 (14)0.43848 (19)0.0227 (5)
H3110.44420.93470.43660.029 (5)*
H3120.31260.95060.38810.029 (5)*
C320.4067 (2)1.05953 (15)0.40242 (19)0.0243 (5)
H3210.47821.07970.44950.030 (5)*
H3220.41681.05620.32920.030 (5)*
C330.3134 (2)1.12142 (14)0.40473 (19)0.0232 (5)
H3310.24351.09860.35590.031 (4)*
O330.33349 (16)1.19994 (10)0.36145 (14)0.0300 (4)
H330.387 (2)1.225 (2)0.402 (2)0.063 (8)*
C340.28831 (19)1.12850 (14)0.51480 (19)0.0204 (5)
C350.26916 (17)1.03865 (13)0.55319 (18)0.0181 (4)
H350.20141.01790.49940.031 (4)*
C360.2348 (2)1.03607 (14)0.65826 (19)0.0228 (5)
H3610.30181.04500.71800.031 (5)*
H3620.18021.08120.65980.031 (5)*
C370.1818 (2)0.95215 (15)0.6708 (2)0.0228 (5)
H3710.11320.94510.61230.033 (5)*
H3720.15850.95200.73850.033 (5)*
C380.26091 (18)0.87747 (14)0.67029 (18)0.0196 (5)
C390.31363 (17)0.88578 (14)0.57250 (17)0.0176 (4)
H390.24920.87620.50920.031 (4)*
C400.36224 (17)0.97260 (14)0.55178 (17)0.0174 (4)
C410.39175 (19)0.81162 (14)0.57326 (19)0.0222 (5)
O410.48323 (14)0.81579 (10)0.55101 (15)0.0273 (4)
C420.3518 (2)0.73038 (15)0.6013 (2)0.0329 (6)
H4210.39240.68220.59030.031 (4)*
C430.2621 (2)0.71939 (15)0.6414 (2)0.0306 (6)
C440.1919 (2)0.79335 (15)0.6609 (2)0.0251 (5)
C450.161 (2)0.7699 (11)0.764 (2)0.032 (2)0.557 (4)
H4510.23110.75970.81920.036 (6)*0.557 (4)
H4520.12290.81830.78720.036 (6)*0.557 (4)
C460.0848 (17)0.6943 (10)0.758 (2)0.0439 (19)0.557 (4)
H4610.01800.69750.69740.036 (6)*0.557 (4)
H4620.06030.68690.82500.036 (6)*0.557 (4)
C470.1661 (7)0.6252 (6)0.7437 (7)0.0365 (18)0.557 (4)
C480.2400 (7)0.6352 (6)0.6817 (7)0.0259 (16)0.557 (4)
C490.3009 (5)0.5626 (4)0.6522 (5)0.0278 (12)0.557 (4)
H4910.37820.56220.69890.062 (7)*0.557 (4)
H4920.30730.57070.57840.062 (7)*0.557 (4)
C500.247 (2)0.476 (3)0.6595 (16)0.0299 (9)0.557 (4)
C510.2104 (4)0.4726 (3)0.7625 (4)0.0316 (11)0.557 (4)
H5110.17500.41790.76760.062 (7)*0.557 (4)
H5120.27760.47720.82300.062 (7)*0.557 (4)
C520.1282 (6)0.5408 (4)0.7713 (6)0.0375 (14)0.557 (4)
H5210.05390.52800.72320.062 (7)*0.557 (4)
H5220.11910.54220.84490.062 (7)*0.557 (4)
C530.1790 (2)1.17875 (16)0.5008 (2)0.0306 (6)
H5310.18421.23000.46150.033 (4)*
H5320.16761.19280.57080.033 (4)*
H5330.11531.14540.46130.033 (4)*
C540.3818 (2)1.17710 (15)0.5922 (2)0.0249 (5)
H5410.37971.23560.57010.036 (4)*
H5420.45511.15310.59190.036 (4)*
H5430.37031.17370.66410.036 (4)*
C550.47564 (18)0.99181 (15)0.6325 (2)0.0237 (5)
H5510.51440.93950.65760.029 (4)*
H5520.46141.02250.69310.029 (4)*
H5530.52281.02560.59800.029 (4)*
C560.3544 (2)0.87866 (16)0.77538 (19)0.0287 (5)
H5610.40300.92720.77610.041 (5)*
H5620.39930.82760.78090.041 (5)*
H5630.31990.88190.83570.041 (5)*
C570.0847 (2)0.79513 (17)0.5679 (2)0.0371 (7)
H5710.05640.73830.55210.047 (5)*
H5720.10290.81910.50480.047 (5)*
H5730.02690.82920.58780.047 (5)*
C590.1462 (6)0.4640 (4)0.5643 (5)0.0533 (17)0.557 (4)
H5910.17230.45990.49910.066 (6)*0.557 (4)
H5920.09500.51160.55890.066 (6)*0.557 (4)
H5930.10640.41280.57390.066 (6)*0.557 (4)
C600.3364 (7)0.4090 (4)0.6623 (8)0.057 (2)0.557 (4)
H6010.40070.41880.72310.066 (6)*0.557 (4)
H6020.36150.41110.59640.066 (6)*0.557 (4)
H6030.30400.35410.66920.066 (6)*0.557 (4)
C750.151 (3)0.7840 (15)0.765 (3)0.032 (2)0.443 (4)
H7510.21440.79120.82840.036 (6)*0.443 (4)
H7520.09290.82660.76750.036 (6)*0.443 (4)
C760.101 (2)0.6971 (13)0.764 (3)0.0439 (19)0.443 (4)
H7610.01830.70370.73930.036 (6)*0.443 (4)
H7620.11670.67890.83900.036 (6)*0.443 (4)
C770.1322 (8)0.6236 (7)0.7014 (8)0.0305 (19)0.443 (4)
C780.2109 (9)0.6345 (8)0.6472 (7)0.0195 (16)0.443 (4)
C790.2649 (7)0.5606 (5)0.6046 (6)0.0277 (15)0.443 (4)
H7910.23510.55790.52650.062 (7)*0.443 (4)
H7920.34710.57000.61950.062 (7)*0.443 (4)
C800.243 (3)0.478 (4)0.653 (2)0.0299 (9)0.443 (4)
C810.1184 (6)0.4708 (4)0.6487 (6)0.0394 (15)0.443 (4)
H8110.07370.47520.57410.062 (7)*0.443 (4)
H8120.10290.41580.67640.062 (7)*0.443 (4)
C820.0838 (7)0.5386 (5)0.7140 (8)0.0408 (18)0.443 (4)
H8210.10720.52250.78990.062 (7)*0.443 (4)
H8220.00060.54270.69410.062 (7)*0.443 (4)
C890.2759 (8)0.4065 (4)0.5871 (8)0.051 (2)0.443 (4)
H8910.27240.35330.62320.066 (6)*0.443 (4)
H8920.35250.41550.57960.066 (6)*0.443 (4)
H8930.22340.40530.51650.066 (6)*0.443 (4)
C900.3167 (7)0.4700 (5)0.7668 (6)0.0491 (19)0.443 (4)
H9010.30580.51930.80760.066 (6)*0.443 (4)
H9020.39610.46600.76550.066 (6)*0.443 (4)
H9030.29510.42000.80010.066 (6)*0.443 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0153 (11)0.0214 (11)0.0293 (13)0.0018 (9)0.0057 (9)0.0022 (9)
C20.0197 (11)0.0241 (12)0.0332 (14)−0.0016 (10)0.0091 (10)0.0048 (10)
C30.0245 (12)0.0204 (11)0.0318 (13)−0.0014 (10)0.0078 (10)0.0043 (10)
O30.0298 (10)0.0244 (10)0.0685 (14)−0.0020 (8)0.0190 (10)0.0115 (9)
C40.0209 (11)0.0174 (11)0.0254 (12)0.0030 (9)0.0082 (9)0.0060 (9)
C50.0149 (10)0.0173 (10)0.0209 (11)0.0022 (8)0.0047 (8)0.0017 (9)
C60.0134 (10)0.0214 (11)0.0322 (13)0.0043 (9)0.0043 (9)0.0041 (10)
C70.0134 (10)0.0218 (11)0.0355 (14)0.0013 (9)0.0079 (9)0.0013 (10)
C80.0093 (9)0.0196 (11)0.0275 (12)−0.0006 (8)−0.0004 (9)−0.0018 (9)
C90.0128 (10)0.0169 (10)0.0202 (11)0.0005 (8)0.0011 (8)−0.0012 (8)
C100.0143 (10)0.0188 (10)0.0199 (11)0.0015 (8)0.0032 (8)0.0011 (9)
C110.0160 (10)0.0206 (11)0.0240 (11)0.0010 (9)0.0032 (9)−0.0016 (9)
O110.0253 (8)0.0237 (8)0.0396 (10)0.0047 (7)0.0159 (8)0.0006 (8)
C120.0195 (10)0.0174 (11)0.0247 (12)0.0038 (9)0.0034 (9)−0.0018 (9)
C130.0146 (10)0.0182 (11)0.0220 (11)−0.0013 (9)−0.0028 (8)−0.0017 (9)
C140.0128 (10)0.0187 (10)0.0268 (12)−0.0003 (9)0.0026 (9)−0.0039 (9)
C150.0140 (10)0.0244 (12)0.0374 (14)−0.0017 (9)0.0032 (10)0.0043 (11)
C160.0188 (11)0.0237 (12)0.0418 (15)−0.0028 (10)0.0055 (10)0.0049 (11)
C170.0222 (12)0.0209 (11)0.0352 (14)−0.0024 (10)0.0025 (10)0.0011 (10)
C180.0190 (11)0.0176 (11)0.0258 (12)−0.0023 (9)−0.0017 (9)−0.0021 (9)
C190.0226 (11)0.0186 (11)0.0295 (13)−0.0001 (9)0.0007 (10)−0.0021 (10)
C200.0239 (12)0.0182 (11)0.0395 (15)−0.0006 (10)−0.0051 (11)−0.0029 (10)
C210.0318 (14)0.0232 (13)0.0480 (17)−0.0018 (11)0.0033 (12)0.0082 (12)
C220.0328 (14)0.0273 (13)0.0506 (18)−0.0017 (12)0.0119 (13)0.0079 (12)
C230.0313 (13)0.0181 (11)0.0371 (15)0.0031 (10)0.0131 (11)0.0030 (10)
C240.0280 (12)0.0301 (13)0.0323 (14)0.0075 (11)0.0080 (10)0.0108 (11)
C250.0252 (12)0.0266 (12)0.0239 (12)0.0048 (10)0.0047 (10)−0.0015 (10)
C260.0195 (11)0.0234 (12)0.0322 (13)−0.0024 (10)−0.0043 (10)−0.0002 (10)
C270.0194 (11)0.0206 (11)0.0267 (12)0.0009 (9)0.0057 (9)−0.0020 (9)
C290.0310 (14)0.0204 (12)0.0451 (16)0.0021 (11)−0.0030 (12)−0.0006 (11)
C300.0352 (15)0.0260 (13)0.058 (2)−0.0010 (12)−0.0126 (14)−0.0082 (13)
C310.0256 (11)0.0195 (11)0.0245 (12)−0.0029 (10)0.0090 (9)−0.0028 (9)
C320.0255 (12)0.0222 (11)0.0261 (12)−0.0029 (10)0.0079 (10)0.0014 (10)
C330.0228 (11)0.0194 (11)0.0242 (12)−0.0043 (9)−0.0002 (9)0.0030 (9)
O330.0358 (10)0.0218 (9)0.0288 (10)−0.0029 (8)0.0014 (8)0.0079 (7)
C340.0181 (10)0.0157 (10)0.0251 (12)0.0013 (9)0.0011 (9)0.0008 (9)
C350.0125 (10)0.0176 (11)0.0212 (11)−0.0011 (8)−0.0014 (8)−0.0008 (8)
C360.0238 (12)0.0189 (11)0.0261 (13)0.0045 (9)0.0069 (10)−0.0007 (9)
C370.0209 (11)0.0205 (11)0.0292 (13)0.0036 (9)0.0106 (10)0.0009 (10)
C380.0172 (10)0.0193 (11)0.0221 (12)0.0030 (9)0.0045 (9)0.0025 (9)
C390.0138 (10)0.0179 (10)0.0200 (11)−0.0005 (9)0.0021 (8)−0.0012 (9)
C400.0139 (10)0.0163 (10)0.0206 (11)−0.0009 (8)0.0015 (8)−0.0022 (9)
C410.0212 (11)0.0179 (11)0.0290 (13)0.0015 (9)0.0094 (10)−0.0011 (9)
O410.0216 (8)0.0195 (8)0.0447 (11)0.0025 (7)0.0158 (8)0.0011 (7)
C420.0335 (14)0.0166 (12)0.0562 (18)0.0057 (10)0.0256 (13)0.0018 (11)
C430.0301 (14)0.0192 (12)0.0485 (16)0.0022 (10)0.0213 (12)0.0025 (11)
C440.0236 (12)0.0183 (11)0.0372 (14)0.0018 (10)0.0146 (11)0.0036 (10)
C450.043 (4)0.014 (6)0.0527 (18)0.012 (4)0.034 (3)0.005 (4)
C460.047 (5)0.0273 (16)0.073 (3)0.002 (2)0.044 (3)0.0098 (16)
C470.040 (5)0.023 (3)0.054 (5)0.004 (3)0.026 (4)0.006 (4)
C480.019 (4)0.020 (2)0.039 (5)0.005 (3)0.007 (3)0.006 (4)
C490.030 (3)0.017 (2)0.040 (4)0.000 (2)0.016 (3)0.000 (3)
C500.0395 (19)0.0182 (16)0.035 (2)−0.0023 (14)0.0144 (13)0.003 (3)
C510.043 (3)0.018 (2)0.037 (3)0.0040 (19)0.015 (2)0.0093 (19)
C520.049 (4)0.026 (3)0.047 (4)0.006 (3)0.030 (3)0.009 (3)
C530.0240 (12)0.0239 (12)0.0433 (15)0.0070 (10)0.0071 (11)0.0065 (11)
C540.0265 (12)0.0172 (11)0.0283 (13)−0.0024 (10)0.0016 (10)−0.0021 (9)
C550.0138 (10)0.0211 (11)0.0323 (13)−0.0009 (9)−0.0013 (9)0.0008 (9)
C560.0313 (13)0.0297 (13)0.0232 (13)0.0045 (11)0.0032 (10)0.0036 (10)
C570.0231 (12)0.0283 (14)0.0588 (19)−0.0108 (11)0.0082 (12)0.0026 (13)
C590.066 (4)0.059 (4)0.034 (3)−0.029 (3)0.009 (2)−0.012 (3)
C600.073 (5)0.025 (3)0.091 (6)0.009 (3)0.054 (5)0.006 (3)
C750.043 (4)0.014 (6)0.0527 (18)0.012 (4)0.034 (3)0.005 (4)
C760.047 (5)0.0273 (16)0.073 (3)0.002 (2)0.044 (3)0.0098 (16)
C770.031 (5)0.024 (3)0.040 (6)−0.001 (4)0.015 (4)0.004 (4)
C780.015 (5)0.022 (3)0.018 (5)0.001 (3)−0.003 (3)0.003 (4)
C790.038 (5)0.019 (3)0.027 (4)−0.004 (3)0.009 (3)0.001 (3)
C800.0395 (19)0.0182 (16)0.035 (2)−0.0023 (14)0.0144 (13)0.003 (3)
C810.046 (3)0.028 (3)0.045 (4)−0.013 (3)0.014 (3)0.002 (3)
C820.046 (5)0.031 (3)0.051 (5)−0.012 (3)0.022 (4)0.002 (4)
C890.072 (6)0.021 (3)0.070 (6)−0.002 (4)0.040 (5)0.000 (3)
C900.059 (5)0.038 (4)0.045 (4)0.005 (3)0.002 (3)0.019 (3)
Geometric parameters (Å, º) top
C1—C21.531 (3)C35—C361.526 (3)
C1—C101.556 (3)C35—C401.562 (3)
C1—H110.99C35—H351.00
C1—H120.99C36—C371.522 (3)
C2—C31.522 (3)C36—H3610.99
C2—H210.99C36—H3620.99
C2—H220.99C37—C381.544 (3)
C3—O31.433 (3)C37—H3710.99
C3—C41.534 (3)C37—H3720.99
C3—H311.00C38—C561.548 (3)
O3—H30.84C38—C391.568 (3)
C4—C241.536 (3)C38—C441.583 (3)
C4—C231.543 (3)C39—C411.527 (3)
C4—C51.559 (3)C39—C401.566 (3)
C5—C61.532 (3)C39—H391.00
C5—C101.558 (3)C40—C551.550 (3)
C5—H51.00C41—O411.229 (3)
C6—C71.525 (3)C41—C421.471 (3)
C6—H610.99C42—C431.341 (3)
C6—H620.99C42—H4210.95
C7—C81.544 (3)C43—C481.498 (10)
C7—H710.99C43—C781.510 (13)
C7—H720.99C43—C441.525 (3)
C8—C261.544 (3)C44—C451.53 (3)
C8—C91.573 (3)C44—C571.548 (4)
C8—C141.585 (3)C44—C751.57 (4)
C9—C111.517 (3)C45—C461.521 (6)
C9—C101.571 (3)C45—H4510.99
C9—H91.00C45—H4520.99
C10—C251.549 (3)C46—C471.535 (8)
C11—O111.236 (3)C46—H4610.99
C11—C121.465 (3)C46—H4620.99
C12—C131.348 (3)C47—C481.365 (13)
C12—H1210.95C47—C521.504 (11)
C13—C181.481 (3)C48—C491.485 (12)
C13—C141.532 (3)C49—C501.55 (6)
C14—C151.538 (3)C49—H4910.99
C14—C271.545 (3)C49—H4920.99
C15—C161.523 (3)C50—C511.52 (4)
C15—H1510.99C50—C591.529 (12)
C15—H1520.99C50—C601.530 (12)
C16—C171.504 (3)C51—C521.512 (7)
C16—H1610.99C51—H5110.99
C16—H1620.99C51—H5120.99
C17—C181.352 (4)C52—H5210.99
C17—C221.507 (4)C52—H5220.99
C18—C191.520 (3)C53—H5310.98
C19—C201.536 (3)C53—H5320.98
C19—H1910.99C53—H5330.98
C19—H1920.99C54—H5410.98
C20—C211.528 (4)C54—H5420.98
C20—C291.534 (3)C54—H5430.98
C20—C301.536 (4)C55—H5510.98
C21—C221.529 (4)C55—H5520.98
C21—H2110.99C55—H5530.98
C21—H2120.99C56—H5610.98
C22—H2210.99C56—H5620.98
C22—H2220.99C56—H5630.98
C23—H2310.98C57—H5710.98
C23—H2320.98C57—H5720.98
C23—H2330.98C57—H5730.98
C24—H2410.98C59—H5910.98
C24—H2420.98C59—H5920.98
C24—H2430.98C59—H5930.98
C25—H2510.98C60—H6010.98
C25—H2520.98C60—H6020.98
C25—H2530.98C60—H6030.98
C26—H2610.98C75—C761.521 (6)
C26—H2620.98C75—H7510.99
C26—H2630.98C75—H7520.99
C27—H2710.98C76—C771.535 (8)
C27—H2720.98C76—H7610.99
C27—H2730.98C76—H7620.99
C29—H2910.98C77—C781.341 (17)
C29—H2920.98C77—C821.513 (14)
C29—H2930.98C78—C791.527 (16)
C30—H3010.98C79—C801.52 (7)
C30—H3020.98C79—H7910.99
C30—H3030.98C79—H7920.99
C31—C321.532 (3)C80—C811.53 (4)
C31—C401.545 (3)C80—C901.534 (16)
C31—H3110.99C80—C891.534 (16)
C31—H3120.99C81—C821.505 (11)
C32—C331.522 (3)C81—H8110.99
C32—H3210.99C81—H8120.99
C32—H3220.99C82—H8210.99
C33—O331.427 (3)C82—H8220.99
C33—C341.540 (3)C89—H8910.98
C33—H3311.00C89—H8920.98
O33—H330.84C89—H8930.98
C34—C541.536 (3)C90—H9010.98
C34—C531.537 (3)C90—H9020.98
C34—C351.563 (3)C90—H9030.98
C2—C1—C10112.23 (19)C33—C34—C35107.99 (18)
C2—C1—H11109.2C36—C35—C40110.97 (18)
C10—C1—H11109.2C36—C35—C34114.04 (18)
C2—C1—H12109.2C40—C35—C34117.02 (17)
C10—C1—H12109.2C36—C35—H35104.4
H11—C1—H12107.9C40—C35—H35104.4
C3—C2—C1112.11 (19)C34—C35—H35104.4
C3—C2—H21109.2C37—C36—C35109.91 (19)
C1—C2—H21109.2C37—C36—H361109.7
C3—C2—H22109.2C35—C36—H361109.7
C1—C2—H22109.2C37—C36—H362109.7
H21—C2—H22107.9C35—C36—H362109.7
O3—C3—C2112.1 (2)H361—C36—H362108.2
O3—C3—C4106.37 (19)C36—C37—C38113.62 (18)
C2—C3—C4113.7 (2)C36—C37—H371108.8
O3—C3—H31108.1C38—C37—H371108.8
C2—C3—H31108.1C36—C37—H372108.8
C4—C3—H31108.1C38—C37—H372108.8
C3—O3—H3107 (3)H371—C37—H372107.7
C3—C4—C24111.00 (19)C37—C38—C56108.34 (19)
C3—C4—C23107.0 (2)C37—C38—C39108.93 (18)
C24—C4—C23107.08 (19)C56—C38—C39110.42 (18)
C3—C4—C5108.51 (18)C37—C38—C44109.75 (18)
C24—C4—C5113.8 (2)C56—C38—C44110.06 (19)
C23—C4—C5109.21 (18)C39—C38—C44109.32 (18)
C6—C5—C10110.90 (18)C41—C39—C40115.46 (17)
C6—C5—C4113.39 (18)C41—C39—C38108.27 (18)
C10—C5—C4116.46 (18)C40—C39—C38117.82 (17)
C6—C5—H5104.9C41—C39—H39104.6
C10—C5—H5104.9C40—C39—H39104.6
C4—C5—H5104.9C38—C39—H39104.6
C7—C6—C5109.55 (19)C31—C40—C55108.89 (18)
C7—C6—H61109.8C31—C40—C35107.13 (18)
C5—C6—H61109.8C55—C40—C35113.10 (18)
C7—C6—H62109.8C31—C40—C39108.42 (17)
C5—C6—H62109.8C55—C40—C39112.14 (18)
H61—C6—H62108.2C35—C40—C39106.95 (16)
C6—C7—C8113.32 (19)O41—C41—C42119.2 (2)
C6—C7—H71108.9O41—C41—C39124.4 (2)
C8—C7—H71108.9C42—C41—C39116.45 (19)
C6—C7—H72108.9C43—C42—C41124.7 (2)
C8—C7—H72108.9C43—C42—H421117.6
H71—C7—H72107.7C41—C42—H421117.6
C26—C8—C7108.43 (19)C42—C43—C48119.4 (4)
C26—C8—C9110.93 (19)C42—C43—C78122.0 (5)
C7—C8—C9108.94 (18)C42—C43—C44120.9 (2)
C26—C8—C14109.62 (19)C48—C43—C44119.1 (4)
C7—C8—C14109.73 (19)C78—C43—C44115.8 (5)
C9—C8—C14109.17 (17)C43—C44—C45103.2 (8)
C11—C9—C10115.80 (18)C43—C44—C57106.8 (2)
C11—C9—C8108.38 (18)C45—C44—C57109.8 (10)
C10—C9—C8118.15 (17)C43—C44—C75112.7 (10)
C11—C9—H9104.3C57—C44—C75106.4 (13)
C10—C9—H9104.3C43—C44—C38111.34 (18)
C8—C9—H9104.3C45—C44—C38112.8 (8)
C25—C10—C1109.20 (18)C57—C44—C38112.2 (2)
C25—C10—C5114.17 (18)C75—C44—C38107.3 (10)
C1—C10—C5106.40 (18)C46—C45—C44116 (2)
C25—C10—C9112.15 (18)C46—C45—H451108.3
C1—C10—C9108.15 (17)C44—C45—H451108.3
C5—C10—C9106.45 (17)C46—C45—H452108.3
O11—C11—C12119.2 (2)C44—C45—H452108.3
O11—C11—C9123.3 (2)H451—C45—H452107.4
C12—C11—C9117.56 (19)C45—C46—C47100.0 (13)
C13—C12—C11124.7 (2)C45—C46—H461111.8
C13—C12—H121117.7C47—C46—H461111.8
C11—C12—H121117.7C45—C46—H462111.8
C12—C13—C18121.1 (2)C47—C46—H462111.8
C12—C13—C14120.3 (2)H461—C46—H462109.5
C18—C13—C14118.49 (19)C48—C47—C52122.5 (8)
C13—C14—C15107.62 (18)C48—C47—C46122.5 (12)
C13—C14—C27107.32 (18)C52—C47—C46111.8 (10)
C15—C14—C27107.84 (19)C47—C48—C49120.7 (8)
C13—C14—C8109.97 (18)C47—C48—C43121.1 (8)
C15—C14—C8111.49 (18)C49—C48—C43118.2 (7)
C27—C14—C8112.40 (18)C48—C49—C50116.0 (8)
C16—C15—C14111.74 (19)C48—C49—H491108.3
C16—C15—H151109.3C50—C49—H491108.3
C14—C15—H151109.3C48—C49—H492108.3
C16—C15—H152109.3C50—C49—H492108.3
C14—C15—H152109.3H491—C49—H492107.4
H151—C15—H152107.9C51—C50—C59110 (2)
C17—C16—C15111.6 (2)C51—C50—C60109 (2)
C17—C16—H161109.3C59—C50—C60111.1 (13)
C15—C16—H161109.3C51—C50—C49108.2 (13)
C17—C16—H162109.3C59—C50—C49110 (2)
C15—C16—H162109.3C60—C50—C49109 (2)
H161—C16—H162108.0C52—C51—C50113.0 (11)
C18—C17—C16122.2 (2)C52—C51—H511109.0
C18—C17—C22123.1 (2)C50—C51—H511109.0
C16—C17—C22114.6 (2)C52—C51—H512109.0
C17—C18—C13121.2 (2)C50—C51—H512109.0
C17—C18—C19120.9 (2)H511—C51—H512107.8
C13—C18—C19117.9 (2)C47—C52—C51112.5 (5)
C18—C19—C20115.1 (2)C47—C52—H521109.1
C18—C19—H191108.5C51—C52—H521109.1
C20—C19—H191108.5C47—C52—H522109.1
C18—C19—H192108.5C51—C52—H522109.1
C20—C19—H192108.5H521—C52—H522107.8
H191—C19—H192107.5C34—C53—H531109.5
C21—C20—C29109.6 (2)C34—C53—H532109.5
C21—C20—C19108.1 (2)H531—C53—H532109.5
C29—C20—C19109.6 (2)C34—C53—H533109.5
C21—C20—C30110.8 (2)H531—C53—H533109.5
C29—C20—C30108.9 (2)H532—C53—H533109.5
C19—C20—C30109.7 (2)C34—C54—H541109.5
C20—C21—C22112.2 (2)C34—C54—H542109.5
C20—C21—H211109.2H541—C54—H542109.5
C22—C21—H211109.2C34—C54—H543109.5
C20—C21—H212109.2H541—C54—H543109.5
C22—C21—H212109.2H542—C54—H543109.5
H211—C21—H212107.9C40—C55—H551109.5
C17—C22—C21113.2 (2)C40—C55—H552109.5
C17—C22—H221108.9H551—C55—H552109.5
C21—C22—H221108.9C40—C55—H553109.5
C17—C22—H222108.9H551—C55—H553109.5
C21—C22—H222108.9H552—C55—H553109.5
H221—C22—H222107.8C38—C56—H561109.5
C4—C23—H231109.5C38—C56—H562109.5
C4—C23—H232109.5H561—C56—H562109.5
H231—C23—H232109.5C38—C56—H563109.5
C4—C23—H233109.5H561—C56—H563109.5
H231—C23—H233109.5H562—C56—H563109.5
H232—C23—H233109.5C44—C57—H571109.5
C4—C24—H241109.5C44—C57—H572109.5
C4—C24—H242109.5H571—C57—H572109.5
H241—C24—H242109.5C44—C57—H573109.5
C4—C24—H243109.5H571—C57—H573109.5
H241—C24—H243109.5H572—C57—H573109.5
H242—C24—H243109.5C76—C75—C44107 (2)
C10—C25—H251109.5C76—C75—H751110.3
C10—C25—H252109.5C44—C75—H751110.3
H251—C25—H252109.5C76—C75—H752110.3
C10—C25—H253109.5C44—C75—H752110.3
H251—C25—H253109.5H751—C75—H752108.6
H252—C25—H253109.5C75—C76—C77124 (2)
C8—C26—H261109.5C75—C76—H761106.3
C8—C26—H262109.5C77—C76—H761106.3
H261—C26—H262109.5C75—C76—H762106.3
C8—C26—H263109.5C77—C76—H762106.3
H261—C26—H263109.5H761—C76—H762106.4
H262—C26—H263109.5C78—C77—C82121.8 (10)
C14—C27—H271109.5C78—C77—C76119.0 (15)
C14—C27—H272109.5C82—C77—C76118.7 (14)
H271—C27—H272109.5C77—C78—C43120.4 (11)
C14—C27—H273109.5C77—C78—C79121.5 (11)
H271—C27—H273109.5C43—C78—C79117.4 (9)
H272—C27—H273109.5C80—C79—C78113.4 (9)
C20—C29—H291109.5C80—C79—H791108.9
C20—C29—H292109.5C78—C79—H791108.9
H291—C29—H292109.5C80—C79—H792108.9
C20—C29—H293109.5C78—C79—H792108.9
H291—C29—H293109.5H791—C79—H792107.7
H292—C29—H293109.5C79—C80—C81108.9 (16)
C20—C30—H301109.5C79—C80—C90110 (3)
C20—C30—H302109.5C81—C80—C90112 (3)
H301—C30—H302109.5C79—C80—C89109 (3)
C20—C30—H303109.5C81—C80—C89109 (3)
H301—C30—H303109.5C90—C80—C89107.9 (16)
H302—C30—H303109.5C82—C81—C80110.6 (12)
C32—C31—C40112.41 (18)C82—C81—H811109.5
C32—C31—H311109.1C80—C81—H811109.5
C40—C31—H311109.1C82—C81—H812109.5
C32—C31—H312109.1C80—C81—H812109.5
C40—C31—H312109.1H811—C81—H812108.1
H311—C31—H312107.9C81—C82—C77114.7 (7)
C33—C32—C31112.04 (19)C81—C82—H821108.6
C33—C32—H321109.2C77—C82—H821108.6
C31—C32—H321109.2C81—C82—H822108.6
C33—C32—H322109.2C77—C82—H822108.6
C31—C32—H322109.2H821—C82—H822107.6
H321—C32—H322107.9C80—C89—H891109.5
O33—C33—C32111.34 (19)C80—C89—H892109.5
O33—C33—C34113.27 (19)H891—C89—H892109.5
C32—C33—C34113.07 (19)C80—C89—H893109.5
O33—C33—H331106.2H891—C89—H893109.5
C32—C33—H331106.2H892—C89—H893109.5
C34—C33—H331106.2C80—C90—H901109.5
C33—O33—H33112 (3)C80—C90—H902109.5
C54—C34—C53107.3 (2)H901—C90—H902109.5
C54—C34—C33110.85 (19)C80—C90—H903109.5
C53—C34—C33107.43 (19)H901—C90—H903109.5
C54—C34—C35114.02 (19)H902—C90—H903109.5
C53—C34—C35109.02 (18)
C10—C1—C2—C3−57.5 (3)C37—C38—C39—C41179.90 (18)
C1—C2—C3—O3175.5 (2)C56—C38—C39—C4161.0 (2)
C1—C2—C3—C454.7 (3)C44—C38—C39—C41−60.2 (2)
O3—C3—C4—C24−48.6 (3)C37—C38—C39—C4046.6 (2)
C2—C3—C4—C2475.4 (3)C56—C38—C39—C40−72.3 (2)
O3—C3—C4—C2368.0 (2)C44—C38—C39—C40166.49 (18)
C2—C3—C4—C23−168.1 (2)C32—C31—C40—C55−68.7 (2)
O3—C3—C4—C5−174.30 (19)C32—C31—C40—C3553.9 (2)
C2—C3—C4—C5−50.3 (3)C32—C31—C40—C39169.01 (18)
C3—C4—C5—C6−176.4 (2)C36—C35—C40—C31173.24 (18)
C24—C4—C5—C659.5 (3)C34—C35—C40—C31−53.5 (2)
C23—C4—C5—C6−60.1 (3)C36—C35—C40—C55−66.8 (2)
C3—C4—C5—C1053.1 (3)C34—C35—C40—C5566.5 (2)
C24—C4—C5—C10−71.0 (3)C36—C35—C40—C3957.2 (2)
C23—C4—C5—C10169.4 (2)C34—C35—C40—C39−169.58 (18)
C10—C5—C6—C7−65.1 (2)C41—C39—C40—C3164.2 (2)
C4—C5—C6—C7161.72 (19)C38—C39—C40—C31−165.71 (18)
C5—C6—C7—C860.4 (3)C41—C39—C40—C55−56.0 (2)
C6—C7—C8—C2671.7 (2)C38—C39—C40—C5574.0 (2)
C6—C7—C8—C9−49.2 (3)C41—C39—C40—C35179.43 (18)
C6—C7—C8—C14−168.62 (18)C38—C39—C40—C35−50.5 (2)
C26—C8—C9—C1161.2 (2)C40—C39—C41—O41−5.8 (3)
C7—C8—C9—C11−179.55 (19)C38—C39—C41—O41−140.4 (2)
C14—C8—C9—C11−59.7 (2)C40—C39—C41—C42175.1 (2)
C26—C8—C9—C10−73.1 (2)C38—C39—C41—C4240.5 (3)
C7—C8—C9—C1046.2 (3)O41—C41—C42—C43170.1 (3)
C14—C8—C9—C10166.01 (18)C39—C41—C42—C43−10.8 (4)
C2—C1—C10—C25−68.2 (2)C41—C42—C43—C48−171.0 (4)
C2—C1—C10—C555.5 (2)C41—C42—C43—C78167.0 (4)
C2—C1—C10—C9169.54 (18)C41—C42—C43—C440.4 (5)
C6—C5—C10—C25−66.5 (2)C42—C43—C44—C45−142.6 (10)
C4—C5—C10—C2565.1 (3)C48—C43—C44—C4528.8 (11)
C6—C5—C10—C1172.94 (18)C78—C43—C44—C4550.0 (11)
C4—C5—C10—C1−55.4 (2)C42—C43—C44—C57101.6 (3)
C6—C5—C10—C957.8 (2)C48—C43—C44—C57−87.0 (4)
C4—C5—C10—C9−170.58 (18)C78—C43—C44—C57−65.8 (4)
C11—C9—C10—C25−55.8 (2)C42—C43—C44—C75−141.9 (14)
C8—C9—C10—C2575.2 (2)C48—C43—C44—C7529.5 (14)
C11—C9—C10—C164.7 (2)C78—C43—C44—C7550.7 (14)
C8—C9—C10—C1−164.32 (19)C42—C43—C44—C38−21.3 (4)
C11—C9—C10—C5178.69 (18)C48—C43—C44—C38150.1 (4)
C8—C9—C10—C5−50.3 (2)C78—C43—C44—C38171.3 (4)
C10—C9—C11—O11−8.0 (3)C37—C38—C44—C43170.5 (2)
C8—C9—C11—O11−143.4 (2)C56—C38—C44—C43−70.4 (3)
C10—C9—C11—C12172.83 (19)C39—C38—C44—C4351.1 (3)
C8—C9—C11—C1237.4 (3)C37—C38—C44—C45−74.0 (10)
O11—C11—C12—C13171.2 (2)C56—C38—C44—C4545.2 (10)
C9—C11—C12—C13−9.5 (3)C39—C38—C44—C45166.6 (10)
C11—C12—C13—C18−179.0 (2)C37—C38—C44—C5750.7 (3)
C11—C12—C13—C144.0 (3)C56—C38—C44—C57169.9 (2)
C12—C13—C14—C15−148.8 (2)C39—C38—C44—C57−68.7 (2)
C18—C13—C14—C1534.2 (3)C37—C38—C44—C75−65.8 (13)
C12—C13—C14—C2795.4 (2)C56—C38—C44—C7553.4 (13)
C18—C13—C14—C27−81.6 (2)C39—C38—C44—C75174.8 (13)
C12—C13—C14—C8−27.2 (3)C43—C44—C45—C46−65.2 (17)
C18—C13—C14—C8155.81 (19)C57—C44—C45—C4648.4 (18)
C26—C8—C14—C13−66.9 (2)C75—C44—C45—C46119 (14)
C7—C8—C14—C13174.14 (18)C38—C44—C45—C46174.4 (13)
C9—C8—C14—C1354.8 (2)C44—C45—C46—C4769 (2)
C26—C8—C14—C1552.4 (2)C45—C46—C47—C48−39 (2)
C7—C8—C14—C15−66.6 (2)C45—C46—C47—C52161.2 (15)
C9—C8—C14—C15174.10 (19)C52—C47—C48—C49−9.7 (10)
C26—C8—C14—C27173.62 (18)C46—C47—C48—C49−167.9 (12)
C7—C8—C14—C2754.6 (2)C52—C47—C48—C43170.2 (6)
C9—C8—C14—C27−64.7 (2)C46—C47—C48—C4312.0 (14)
C13—C14—C15—C16−58.5 (3)C42—C43—C48—C47165.3 (5)
C27—C14—C15—C1657.0 (3)C78—C43—C48—C47−91 (3)
C8—C14—C15—C16−179.2 (2)C44—C43—C48—C47−6.2 (8)
C14—C15—C16—C1751.7 (3)C42—C43—C48—C49−14.7 (7)
C15—C16—C17—C18−18.2 (3)C78—C43—C48—C4989 (3)
C15—C16—C17—C22160.9 (2)C44—C43—C48—C49173.7 (4)
C16—C17—C18—C13−6.6 (4)C47—C48—C49—C5021.1 (10)
C22—C17—C18—C13174.3 (2)C43—C48—C49—C50−158.9 (7)
C16—C17—C18—C19174.9 (2)C48—C49—C50—C51−44.0 (7)
C22—C17—C18—C19−4.2 (4)C48—C49—C50—C5976.5 (12)
C12—C13—C18—C17−179.5 (2)C48—C49—C50—C60−161.8 (9)
C14—C13—C18—C17−2.5 (3)C59—C50—C51—C52−62 (3)
C12—C13—C18—C19−0.9 (3)C60—C50—C51—C52175.8 (16)
C14—C13—C18—C19176.1 (2)C49—C50—C51—C5257.9 (9)
C17—C18—C19—C20−14.4 (3)C48—C47—C52—C5122.6 (10)
C13—C18—C19—C20167.0 (2)C46—C47—C52—C51−177.1 (12)
C18—C19—C20—C2145.4 (3)C50—C51—C52—C47−47.7 (18)
C18—C19—C20—C29164.8 (2)C43—C44—C75—C76−48 (2)
C18—C19—C20—C30−75.6 (3)C45—C44—C75—C76−44 (12)
C29—C20—C21—C22−179.7 (2)C57—C44—C75—C7669 (2)
C19—C20—C21—C22−60.3 (3)C38—C44—C75—C76−171.1 (18)
C30—C20—C21—C2260.0 (3)C44—C75—C76—C7724 (4)
C18—C17—C22—C21−10.5 (4)C75—C76—C77—C783 (4)
C16—C17—C22—C21170.4 (2)C75—C76—C77—C82175 (3)
C20—C21—C22—C1743.6 (3)C82—C77—C78—C43−176.6 (7)
C40—C31—C32—C33−58.0 (3)C76—C77—C78—C43−4.3 (18)
C31—C32—C33—O33−174.44 (19)C82—C77—C78—C79−6.3 (12)
C31—C32—C33—C3456.7 (3)C76—C77—C78—C79166.0 (16)
O33—C33—C34—C54−53.9 (3)C42—C43—C78—C77170.2 (6)
C32—C33—C34—C5474.0 (2)C48—C43—C78—C7782 (3)
O33—C33—C34—C5363.1 (2)C44—C43—C78—C77−22.5 (8)
C32—C33—C34—C53−169.1 (2)C42—C43—C78—C79−0.5 (8)
O33—C33—C34—C35−179.47 (18)C48—C43—C78—C79−89 (3)
C32—C33—C34—C35−51.6 (2)C44—C43—C78—C79166.8 (5)
C54—C34—C35—C3660.6 (2)C77—C78—C79—C80−14.6 (12)
C53—C34—C35—C36−59.3 (2)C43—C78—C79—C80156.0 (9)
C33—C34—C35—C36−175.74 (18)C78—C79—C80—C8147.8 (8)
C54—C34—C35—C40−71.3 (3)C78—C79—C80—C90−74.9 (15)
C53—C34—C35—C40168.8 (2)C78—C79—C80—C89166.7 (10)
C33—C34—C35—C4052.4 (2)C79—C80—C81—C82−62.1 (11)
C40—C35—C36—C37−63.8 (2)C90—C80—C81—C8260 (4)
C34—C35—C36—C37161.52 (18)C89—C80—C81—C82179 (2)
C35—C36—C37—C3859.8 (3)C80—C81—C82—C7743 (2)
C36—C37—C38—C5670.9 (2)C78—C77—C82—C81−8.2 (12)
C36—C37—C38—C39−49.3 (3)C76—C77—C82—C81179.5 (16)
C36—C37—C38—C44−168.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O11i0.842.04 (2)2.792 (2)148 (4)
O33—H33···O41ii0.842.13 (2)2.921 (2)158 (4)
Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) −x+1, y+1/2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O11i0.842.04 (2)2.792 (2)148 (4)
O33—H33···O41ii0.842.127 (15)2.921 (2)158 (4)
Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) −x+1, y+1/2, −z+1.
 

References

First citationBruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationJohnson, C. K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
 First citationRuzicka, L., Cohen, S. L., Furter, M. & van der Sluys-Veer, F. C. (1938). Helv. Chim. Acta, 21, 1735–1746.  CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 70| Part 8| August 2014| Page o842
doi:10.1107/S1600536814014998
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