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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): o613.
Published online 2008 February 22. doi:  10.1107/S1600536808004509
PMCID: PMC2960791

(E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol

Abstract

The title steroid, C29H46O4, is a furostene derivative with a C=C double-bond length of 1.353 (3) Å and an E configuration. The side chain is oriented toward the α face of the AE steroidal nucleus and presents a disordered terminal CH2—OH group [occupancies for resolved sites are 0.591 (9) and 0.409 (9)]. The methyl group at C20 attached to ring E is also oriented toward the α face, avoiding steric hindrance with the carbonyl O atom of the acetyl group. The furostene and acetyl functionalities form an α,β-unsaturated ketone system, with an s-cis configuration. All hydr­oxy and carbonyl groups are involved in weak inter­molecular hydrogen bonds. The absolute configuration was assigned from the synthesis.

Related literature

The diacetate of the title compound has been characterized by X-ray crystallography (Sandoval-Ramírez et al., 2003 [triangle]), as well as a related furost-22-ene derivate with the C20 site substituted by a methyl group and an acetyl group (Meza-Reyes et al., 2004 [triangle]).

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Object name is e-64-0o613-scheme1.jpg

Experimental

Crystal data

  • C29H46O4
  • M r = 458.66
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o613-efi1.jpg
  • a = 23.568 (2) Å
  • b = 7.8420 (9) Å
  • c = 14.7840 (14) Å
  • β = 101.046 (5)°
  • V = 2681.7 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 296 (1) K
  • 0.65 × 0.35 × 0.32 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: none
  • 4351 measured reflections
  • 2559 independent reflections
  • 2121 reflections with I > 2σ(I)
  • R int = 0.026
  • 3 standard reflections every 97 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.097
  • S = 1.02
  • 2559 reflections
  • 323 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: XSCANS (Siemens, 1996 [triangle]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Release 5.10; Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL-Plus; mol­ecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

Table 1
Selected torsion angles (°)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004509/rz2197sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004509/rz2197Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by CONACyT (grant 60397).

supplementary crystallographic information

Comment

We are interested in the preparation of new steroidal derivatives, through the cleavage of the F ring in sarsasapogenin (Sandoval-Ramírez et al., 2003; Meza-Reyes et al., 2004). Such reactions are valuable entries to furostenes; the title compound is a new representative of this family.

The molecular conformation of the title compound compares well with that previously observed for the corresponding diacetate (Sandoval-Ramírez et al., 2003). The functionality C22?C23 has a bond length of 1.353 (3) Å [1.355 (3) Å for the diacetate] and is E configured. The side chain C24/C25/C26/O26 is oriented toward the α face of the AE steroidal nucleus (Fig. 1). The terminal group CH2—OH is disordered over two positions (denoted a and b), and has a poorly defined geometry (see Experimental). The acetyl group substituting the furostenic atom C23 forms a s-cis α,β-unsaturated ketone system with the E configuration at the C22?C23 double bond. The methyl group C21 is placed on the α steroidal face, in agreement with a general rule followed by furostenes: the bulkier group at C20 avoids steric hindrance with groups substituting C23 (Meza-Reyes et al., 2004). The solid-state conformation of the title compound is retained in solution, as confirmed by NMR data.

The crystal structure contains rather weak intermolecular hydrogen bonds, involving all hydroxyl (O3', O26a/O26b) and carbonyl (O23") groups. The main contact, O3'—H3'···O23", links molecules into chains running in the [001] direction.

Experimental

(E)-(25S)-23-Acetyl-3β,26-diacetoxy-5β,16β-furost-22-ene (500 mg, 0.9 mmol) was added under stirring to a 10% ethanolic solution of KOH (25 ml), following the reaction course by TLC. After completion, the mixture was treated with saturated NaCl and washed with water. The organic phase was extracted using CH2Cl2 (3×30 ml) and then dried over Na2SO4. After removing solvent, the crude was chromatographed (ethyl acetate/hexane, 2:3). Single crystals were obtained from an ethyl acetate solution, at 298 K. (I) has been characterized by spectroscopy: 1H-NMR, δ (400 MHz, CDCl3, 298 K) 4.10 (1H, s, H-3), 4.96 (1H, ddd, J = 4.2, 7.6 and 11.6 Hz, H-16), 1.86 (1H, d, J = 7.3 Hz, H-17), 0.60 (3H, s, H-18), 0.95 (3H, s, H-19), 3.70 (1H, c, J20–21 = 7.0 Hz, H-20), 2.24 (3H, s, H-232), 1.27 (3H, d, J21–20 = 7.0 Hz, H-21), 2.44 and 2.22 (2H, ABX system, H-24), 3.38 and 3.45 (2H, ABX system, H-26), 0.94 (3H, d, J27–25 = 7.0 Hz, H-27). 13C-NMR, δ (100 MHz, CDCl3, 298 K) 29.87 (C-1), 27.78 (C-2), 66.95 (C-3), 30.38 (C-4), 36.40 (C-5), 26.38 (C-6), 26.44 (C-7), 35.77 (C-8), 39.90 (C-9), 35.22 (C-10), 20.39 (C-11), 38.46 (C-12), 41.75 (C-13), 55.52 (C-14), 34.98 (C-15), 86.29 (C-16), 62.59 (C-17), 13.35 (C-18), 23.81 (C-19), 37.84 (C-20), 20.17 (C-21), 178.60 (C-22), 108.32 (C-23), 33.43 (C-24), 30.27 (C-25), 66.56 (C-26), 17.08 (C-27), 199.08 (C-231), 29.24 (C-232). IR (KBr, νmax, cm-1): 3498 (OH), 1653 (α,β-unsaturated C?O). [α]20D = +119.17 (c = 0.01 g.ml-1, CHCl3).

Refinement

The final part of the lateral chain is badly disordered. Atoms C26 and O26 were modeled over two sites, and occupancies refined with the sum for a single atom constrained to 1. Site occupation factors converged to 0.591 (9) (C26a and O26a) and 0.409 (9) (C26b and O26b). Bond length C25—C26a was restrained to 1.50 (1) Å, while other dimensions were refined freely. The poor geometry for this part probably indicates that the actual disorder is more complex than a two-sites model. C-bonded H atoms were placed in idealized positions and refined as riding to their parent atoms. C—H bond lengths were fixed to 0.98 (methine CH), 0.97 (methylene CH2) or 0.96 Å (methyl CH3) and isotropic displacement parameters calculated as Uiso(H) = xUeq(carrier C) with x = 1.5 (CH3) or x = 1.2 (CH2 and CH). Disordered hydroxyl H atoms H26E and H26F were placed in idealized positions and refined fixing O—H bond lengths to 0.82 Å and Uiso(H) = 1.5Ueq(carrier O). Finally, hydroxyl H atom H3' was found in a difference map and refined with this as-found position and Uiso(H3') = 1.5Ueq(O3'). Measured Friedel pairs (1496) were merged for refinement.

Figures

Fig. 1.
The molecular structure of the title compound with 50% displacement ellipsoids for non-H atoms. Disordered atoms C26b and O26b (lateral chain) have been omitted for clarity.

Crystal data

C29H46O4Dx = 1.136 Mg m3
Mr = 458.66Melting point = 354–356 K
Monoclinic, C2Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 74 reflections
a = 23.568 (2) Åθ = 4.9–12.2º
b = 7.8420 (9) ŵ = 0.07 mm1
c = 14.7840 (14) ÅT = 296 (1) K
β = 101.046 (5)ºCell measurement pressure: 101(2) kPa
V = 2681.7 (5) Å3Irregular, colourless
Z = 40.65 × 0.35 × 0.32 mm
F000 = 1008

Data collection

Bruker P4 diffractometerRint = 0.026
Radiation source: fine-focus sealed tubeθmax = 25.0º
Monochromator: graphiteθmin = 2.0º
T = 296(1) Kh = −1→28
P = 101(2) kPak = −9→5
2θ/ω scansl = −17→17
Absorption correction: none3 standard reflections
4351 measured reflections every 97 reflections
2559 independent reflections intensity decay: 1%
2121 reflections with I > 2σ(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.097  w = 1/[σ2(Fo2) + (0.0494P)2 + 0.4384P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2559 reflectionsΔρmax = 0.13 e Å3
323 parametersΔρmin = −0.13 e Å3
2 restraintsExtinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0026 (5)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
C10.34699 (12)0.0303 (4)0.50200 (18)0.0581 (7)
H1A0.3696−0.02440.46190.070*
H1B0.3400−0.05370.54670.070*
C20.28939 (12)0.0842 (5)0.44463 (18)0.0638 (8)
H2A0.26490.12830.48510.077*
H2B0.2703−0.01470.41300.077*
C30.29628 (11)0.2195 (5)0.37409 (17)0.0601 (8)
H3A0.25800.26180.34530.072*
O3'0.32240 (9)0.1390 (3)0.30500 (12)0.0705 (6)
H3'0.32690.23480.26470.106*
C40.33188 (11)0.3665 (4)0.42067 (17)0.0558 (7)
H4A0.30930.42710.45870.067*
H4B0.33940.44500.37360.067*
C50.38998 (11)0.3145 (4)0.48114 (16)0.0544 (7)
H5A0.41350.26380.44020.065*
C60.42273 (13)0.4707 (5)0.52571 (19)0.0691 (9)
H6A0.42440.55570.47860.083*
H6B0.46210.43800.55240.083*
C70.39424 (13)0.5492 (4)0.60094 (18)0.0612 (8)
H7A0.41830.64130.63070.073*
H7B0.35710.59710.57280.073*
C80.38548 (11)0.4176 (4)0.67347 (16)0.0488 (7)
H8A0.42350.38260.70750.059*
C90.35351 (11)0.2576 (4)0.62918 (16)0.0453 (6)
H9A0.31550.29720.59730.054*
C100.38278 (10)0.1769 (4)0.55348 (16)0.0495 (7)
C110.34185 (13)0.1317 (4)0.70299 (17)0.0554 (7)
H11A0.31830.03880.67300.066*
H11B0.37840.08370.73400.066*
C120.31126 (12)0.2120 (4)0.77530 (17)0.0543 (7)
H12A0.27220.24350.74620.065*
H12B0.30870.12830.82270.065*
C130.34296 (10)0.3699 (3)0.82002 (15)0.0419 (6)
C140.35120 (11)0.4910 (4)0.74173 (16)0.0463 (6)
H14A0.31230.51160.70610.056*
C150.36958 (13)0.6583 (4)0.79078 (17)0.0586 (7)
H15A0.36140.75430.74890.070*
H15B0.41050.65770.81780.070*
C160.33268 (12)0.6649 (4)0.86521 (16)0.0520 (7)
H16A0.30180.74990.85000.062*
C170.30738 (10)0.4861 (4)0.87245 (16)0.0446 (6)
H17A0.26680.48510.84100.054*
C180.40118 (11)0.3167 (4)0.88110 (17)0.0549 (7)
H18A0.42480.26130.84380.082*
H18B0.39400.23970.92810.082*
H18C0.42080.41620.90930.082*
C190.44245 (12)0.1014 (5)0.5966 (2)0.0722 (9)
H19A0.46160.06370.54840.108*
H19B0.43730.00640.63520.108*
H19C0.46550.18710.63280.108*
C200.31059 (10)0.4638 (4)0.97677 (15)0.0460 (6)
H20A0.31990.34540.99510.055*
C210.25366 (14)0.5186 (5)1.0048 (2)0.0666 (8)
H21A0.25900.52341.07080.100*
H21B0.22390.43740.98160.100*
H21C0.24260.62910.97950.100*
C220.35952 (10)0.5804 (4)1.01821 (16)0.0475 (6)
O22'0.36797 (8)0.6985 (3)0.95547 (11)0.0601 (5)
C230.39521 (11)0.5813 (4)1.10164 (16)0.0500 (6)
C23'0.38752 (13)0.4580 (4)1.17199 (17)0.0554 (7)
C23"0.43509 (14)0.4394 (6)1.2564 (2)0.0798 (11)
H23A0.42680.34401.29240.120*
H23B0.43730.54141.29280.120*
H23C0.47140.42111.23740.120*
O23"0.34436 (9)0.3677 (3)1.16669 (12)0.0715 (6)
C240.44328 (12)0.7122 (5)1.11723 (19)0.0615 (8)
H24A0.47310.67251.16750.074*
H24B0.46020.71611.06240.074*
C250.42713 (18)0.8916 (6)1.1391 (3)0.1028 (14)
H25A0.39160.92671.10030.123*0.591 (9)
H25B0.40800.91361.07680.123*0.409 (9)
C26A0.4232 (7)0.9015 (16)1.2456 (6)0.089 (3)0.591 (9)
H26A0.42031.02041.26220.107*0.591 (9)
H26B0.45890.85731.28170.107*0.591 (9)
O26A0.3760 (3)0.8110 (8)1.2709 (5)0.118 (3)0.591 (9)
H26E0.35270.87921.28460.177*0.591 (9)
C26B0.3808 (5)0.9329 (14)1.1735 (7)0.096 (4)0.409 (9)
H26C0.34850.85601.15440.115*0.409 (9)
H26D0.36881.05031.16130.115*0.409 (9)
O26B0.4123 (8)0.903 (3)1.2732 (8)0.123 (5)0.409 (9)
H26F0.39740.96131.30820.184*0.409 (9)
C270.47626 (19)1.0164 (7)1.1335 (3)0.1147 (16)
H27A0.48691.00711.07420.172*
H27B0.50900.98981.18070.172*
H27C0.46371.13071.14210.172*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0725 (17)0.0578 (18)0.0448 (13)0.0020 (16)0.0132 (12)−0.0001 (13)
C20.0620 (15)0.076 (2)0.0531 (14)−0.0184 (16)0.0093 (12)−0.0056 (16)
C30.0535 (14)0.078 (2)0.0470 (13)−0.0013 (16)0.0039 (11)0.0027 (15)
O3'0.0913 (14)0.0727 (15)0.0479 (9)−0.0049 (13)0.0146 (9)0.0015 (11)
C40.0602 (15)0.0618 (19)0.0464 (13)0.0021 (16)0.0126 (12)0.0106 (14)
C50.0495 (14)0.073 (2)0.0425 (13)−0.0035 (14)0.0132 (11)0.0026 (14)
C60.0679 (17)0.088 (2)0.0542 (15)−0.0252 (19)0.0196 (13)0.0086 (18)
C70.0704 (17)0.063 (2)0.0518 (14)−0.0228 (16)0.0146 (13)0.0034 (14)
C80.0441 (12)0.0570 (18)0.0441 (12)−0.0069 (13)0.0058 (10)0.0057 (12)
C90.0416 (12)0.0498 (16)0.0438 (12)−0.0006 (12)0.0067 (10)0.0049 (12)
C100.0456 (13)0.0605 (18)0.0419 (12)0.0030 (13)0.0070 (10)0.0033 (13)
C110.0732 (17)0.0473 (17)0.0463 (13)−0.0074 (15)0.0131 (12)0.0016 (13)
C120.0686 (16)0.0490 (16)0.0480 (13)−0.0094 (15)0.0177 (12)0.0017 (13)
C130.0427 (12)0.0424 (15)0.0400 (12)0.0000 (12)0.0064 (10)0.0053 (12)
C140.0474 (13)0.0468 (16)0.0427 (13)−0.0029 (13)0.0040 (10)0.0047 (12)
C150.0768 (18)0.0463 (17)0.0519 (14)−0.0076 (15)0.0105 (13)0.0070 (14)
C160.0603 (15)0.0444 (16)0.0478 (13)0.0051 (13)0.0018 (11)0.0027 (13)
C170.0389 (12)0.0488 (16)0.0429 (12)0.0007 (12)−0.0005 (9)0.0042 (12)
C180.0548 (14)0.0623 (18)0.0469 (13)0.0127 (14)0.0081 (11)0.0068 (14)
C190.0596 (16)0.098 (3)0.0585 (15)0.0196 (19)0.0089 (13)−0.0004 (19)
C200.0469 (13)0.0458 (15)0.0454 (12)−0.0030 (12)0.0093 (10)−0.0009 (12)
C210.0573 (14)0.075 (2)0.0720 (15)0.0054 (17)0.0229 (12)−0.0050 (17)
C220.0550 (14)0.0441 (14)0.0453 (12)0.0000 (13)0.0142 (11)−0.0016 (13)
O22'0.0774 (12)0.0511 (12)0.0493 (9)−0.0155 (11)0.0058 (8)0.0015 (9)
C230.0502 (13)0.0565 (17)0.0439 (12)−0.0022 (14)0.0101 (11)−0.0066 (13)
C23'0.0585 (16)0.065 (2)0.0432 (13)0.0032 (16)0.0119 (12)−0.0062 (14)
C23"0.0706 (19)0.109 (3)0.0560 (16)0.000 (2)0.0016 (15)0.0168 (19)
O23"0.0800 (13)0.0824 (16)0.0506 (10)−0.0193 (14)0.0090 (9)0.0101 (11)
C240.0533 (15)0.083 (2)0.0492 (13)−0.0108 (17)0.0131 (12)−0.0121 (16)
C250.079 (2)0.067 (2)0.168 (4)−0.021 (2)0.039 (3)−0.038 (3)
C26A0.119 (7)0.087 (5)0.075 (7)−0.029 (5)0.053 (6)−0.040 (6)
O26A0.121 (4)0.106 (4)0.150 (5)−0.022 (4)0.085 (4)−0.043 (4)
C26B0.102 (7)0.080 (7)0.094 (8)0.017 (6)−0.011 (6)−0.028 (6)
O26B0.141 (11)0.182 (12)0.057 (5)0.006 (9)0.047 (6)−0.008 (6)
C270.123 (3)0.101 (3)0.127 (3)−0.054 (3)0.040 (3)−0.029 (3)

Geometric parameters (Å, °)

C1—C21.517 (4)C16—C171.536 (4)
C1—C101.539 (4)C16—H16A0.9800
C1—H1A0.9700C17—C201.540 (3)
C1—H1B0.9700C17—H17A0.9800
C2—C31.518 (4)C18—H18A0.9600
C2—H2A0.9700C18—H18B0.9600
C2—H2B0.9700C18—H18C0.9600
C3—O3'1.436 (3)C19—H19A0.9600
C3—C41.512 (4)C19—H19B0.9600
C3—H3A0.9800C19—H19C0.9600
O3'—H3'0.9770C20—C221.507 (4)
C4—C51.540 (4)C20—C211.539 (4)
C4—H4A0.9700C20—H20A0.9800
C4—H4B0.9700C21—H21A0.9600
C5—C61.528 (5)C21—H21B0.9600
C5—C101.551 (4)C21—H21C0.9600
C5—H5A0.9800C22—O22'1.352 (3)
C6—C71.534 (4)C22—C231.353 (3)
C6—H6A0.9700C23—C23'1.456 (4)
C6—H6B0.9700C23—C241.513 (4)
C7—C81.531 (4)C23'—O23"1.230 (3)
C7—H7A0.9700C23'—C23"1.516 (4)
C7—H7B0.9700C23"—H23A0.9600
C8—C141.522 (4)C23"—H23B0.9600
C8—C91.543 (4)C23"—H23C0.9600
C8—H8A0.9800C24—C251.509 (6)
C9—C111.535 (4)C24—H24A0.9700
C9—C101.557 (3)C24—H24B0.9700
C9—H9A0.9800C25—C26A1.597 (7)
C10—C191.546 (4)C25—C26B1.329 (11)
C11—C121.534 (4)C25—H25A0.9599
C11—H11A0.9700C25—H25B0.9599
C11—H11B0.9700C25—C271.531 (6)
C12—C131.530 (4)C26A—O26A1.428 (15)
C12—H12A0.9700C26A—H26A0.9700
C12—H12B0.9700C26A—H26B0.9700
C13—C141.538 (3)O26A—H26E0.8200
C13—C171.544 (4)C26B—O26B1.536 (18)
C13—C181.548 (3)C26B—H26C0.9700
C14—C151.521 (4)C26B—H26D0.9700
C14—H14A0.9800O26B—H26F0.8200
C15—C161.529 (4)C27—H27A0.9600
C15—H15A0.9700C27—H27B0.9600
C15—H15B0.9700C27—H27C0.9600
C16—O22'1.455 (3)
C2—C1—C10114.6 (3)H15A—C15—H15B109.1
C2—C1—H1A108.6O22'—C16—C15111.2 (2)
C10—C1—H1A108.6O22'—C16—C17105.2 (2)
C2—C1—H1B108.6C15—C16—C17107.5 (2)
C10—C1—H1B108.6O22'—C16—H16A110.9
H1A—C1—H1B107.6C15—C16—H16A110.9
C1—C2—C3112.1 (2)C17—C16—H16A110.9
C1—C2—H2A109.2C16—C17—C20103.2 (2)
C3—C2—H2A109.2C16—C17—C13104.40 (19)
C1—C2—H2B109.2C20—C17—C13120.6 (2)
C3—C2—H2B109.2C16—C17—H17A109.3
H2A—C2—H2B107.9C20—C17—H17A109.3
O3'—C3—C4112.5 (2)C13—C17—H17A109.3
O3'—C3—C2107.4 (3)C13—C18—H18A109.5
C4—C3—C2110.1 (2)C13—C18—H18B109.5
O3'—C3—H3A108.9H18A—C18—H18B109.5
C4—C3—H3A108.9C13—C18—H18C109.5
C2—C3—H3A108.9H18A—C18—H18C109.5
C3—O3'—H3'102.0H18B—C18—H18C109.5
C3—C4—C5114.6 (3)C10—C19—H19A109.5
C3—C4—H4A108.6C10—C19—H19B109.5
C5—C4—H4A108.6H19A—C19—H19B109.5
C3—C4—H4B108.6C10—C19—H19C109.5
C5—C4—H4B108.6H19A—C19—H19C109.5
H4A—C4—H4B107.6H19B—C19—H19C109.5
C6—C5—C4111.0 (3)C22—C20—C21111.1 (2)
C6—C5—C10111.9 (2)C22—C20—C17103.0 (2)
C4—C5—C10112.4 (2)C21—C20—C17111.1 (2)
C6—C5—H5A107.1C22—C20—H20A110.5
C4—C5—H5A107.1C21—C20—H20A110.5
C10—C5—H5A107.1C17—C20—H20A110.5
C5—C6—C7112.3 (2)C20—C21—H21A109.5
C5—C6—H6A109.1C20—C21—H21B109.5
C7—C6—H6A109.1H21A—C21—H21B109.5
C5—C6—H6B109.1C20—C21—H21C109.5
C7—C6—H6B109.1H21A—C21—H21C109.5
H6A—C6—H6B107.9H21B—C21—H21C109.5
C8—C7—C6111.9 (3)O22'—C22—C23118.3 (2)
C8—C7—H7A109.2O22'—C22—C20109.8 (2)
C6—C7—H7A109.2C23—C22—C20131.9 (3)
C8—C7—H7B109.2C22—O22'—C16111.8 (2)
C6—C7—H7B109.2C22—C23—C23'120.5 (3)
H7A—C7—H7B107.9C22—C23—C24117.3 (3)
C14—C8—C7111.7 (3)C23'—C23—C24122.2 (2)
C14—C8—C9108.12 (19)O23"—C23'—C23123.5 (2)
C7—C8—C9111.8 (2)O23"—C23'—C23"118.0 (3)
C14—C8—H8A108.4C23—C23'—C23"118.5 (3)
C7—C8—H8A108.4C23'—C23"—H23A109.5
C9—C8—H8A108.4C23'—C23"—H23B109.5
C11—C9—C8111.15 (19)H23A—C23"—H23B109.5
C11—C9—C10114.4 (2)C23'—C23"—H23C109.5
C8—C9—C10112.8 (2)H23A—C23"—H23C109.5
C11—C9—H9A105.9H23B—C23"—H23C109.5
C8—C9—H9A105.9C25—C24—C23116.9 (2)
C10—C9—H9A105.9C25—C24—H24A108.1
C1—C10—C19106.6 (3)C23—C24—H24A108.1
C1—C10—C5107.51 (19)C25—C24—H24B108.1
C19—C10—C5109.8 (2)C23—C24—H24B108.1
C1—C10—C9112.5 (2)H24A—C24—H24B107.3
C19—C10—C9110.67 (19)C26A—C25—H25A111.5
C5—C10—C9109.6 (2)C26B—C25—H25B93.1
C12—C11—C9113.8 (2)C24—C25—C26A108.7 (6)
C12—C11—H11A108.8C27—C25—C26A102.1 (6)
C9—C11—H11A108.8C26B—C25—C24124.7 (6)
C12—C11—H11B108.8C26B—C25—C27123.3 (6)
C9—C11—H11B108.8C24—C25—C27111.1 (3)
H11A—C11—H11B107.7C24—C25—H25A111.5
C13—C12—C11112.2 (2)C27—C25—H25A111.5
C13—C12—H12A109.2C24—C25—H25B93.1
C11—C12—H12A109.2C27—C25—H25B93.1
C13—C12—H12B109.2O26A—C26A—C25115.4 (8)
C11—C12—H12B109.2O26A—C26A—H26A108.4
H12A—C12—H12B107.9O26A—C26A—H26B108.4
C12—C13—C14107.25 (19)C25—C26A—H26A108.4
C12—C13—C17115.32 (19)C25—C26A—H26B108.4
C14—C13—C1799.9 (2)H26A—C26A—H26B107.5
C12—C13—C18109.8 (2)C26A—O26A—H26E109.5
C14—C13—C18112.3 (2)C25—C26B—H26C113.2
C17—C13—C18111.84 (19)C25—C26B—H26D113.2
C15—C14—C8120.2 (2)H26C—C26B—H26D110.5
C15—C14—C13103.86 (18)C26B—O26B—H26F109.5
C8—C14—C13115.1 (2)C25—C26B—O26B92.8 (8)
C15—C14—H14A105.5O26B—C26B—H26C113.1
C8—C14—H14A105.5O26B—C26B—H26D113.2
C13—C14—H14A105.5C25—C27—H27A109.5
C14—C15—C16102.9 (2)C25—C27—H27B109.5
C14—C15—H15A111.2C25—C27—H27C109.5
C16—C15—H15A111.2H27A—C27—H27B109.5
C14—C15—H15B111.2H27A—C27—H27C109.5
C16—C15—H15B111.2H27B—C27—H27C109.5
C10—C1—C2—C356.9 (3)C18—C13—C14—C861.4 (3)
C1—C2—C3—O3'70.4 (3)C8—C14—C15—C16−168.6 (2)
C1—C2—C3—C4−52.4 (3)C13—C14—C15—C16−38.0 (3)
O3'—C3—C4—C5−67.8 (3)C14—C15—C16—O22'129.1 (2)
C2—C3—C4—C551.9 (3)C14—C15—C16—C1714.4 (3)
C3—C4—C5—C6−179.7 (2)O22'—C16—C17—C2022.5 (2)
C3—C4—C5—C10−53.5 (3)C15—C16—C17—C20141.2 (2)
C4—C5—C6—C770.7 (3)O22'—C16—C17—C13−104.4 (2)
C10—C5—C6—C7−55.8 (3)C15—C16—C17—C1314.3 (2)
C5—C6—C7—C854.0 (3)C12—C13—C17—C16−151.2 (2)
C6—C7—C8—C14−173.6 (2)C14—C13—C17—C16−36.6 (2)
C6—C7—C8—C9−52.3 (3)C18—C13—C17—C1682.4 (2)
C14—C8—C9—C11−53.3 (3)C12—C13—C17—C2093.7 (3)
C7—C8—C9—C11−176.6 (2)C14—C13—C17—C20−151.8 (2)
C14—C8—C9—C10176.6 (2)C18—C13—C17—C20−32.7 (3)
C7—C8—C9—C1053.3 (3)C16—C17—C20—C22−25.8 (2)
C2—C1—C10—C19−172.6 (2)C13—C17—C20—C2290.0 (3)
C2—C1—C10—C5−54.8 (3)C16—C17—C20—C2193.3 (3)
C2—C1—C10—C965.9 (3)C13—C17—C20—C21−150.9 (2)
C6—C5—C10—C1177.4 (2)C21—C20—C22—O22'−98.0 (3)
C4—C5—C10—C151.7 (3)C17—C20—C22—O22'21.0 (3)
C6—C5—C10—C19−67.0 (3)C21—C20—C22—C2384.6 (4)
C4—C5—C10—C19167.4 (2)C17—C20—C22—C23−156.4 (3)
C6—C5—C10—C954.8 (3)C23—C22—O22'—C16170.9 (2)
C4—C5—C10—C9−70.9 (3)C20—C22—O22'—C16−7.0 (3)
C11—C9—C10—C158.2 (3)C15—C16—O22'—C22−126.5 (2)
C8—C9—C10—C1−173.4 (2)C17—C16—O22'—C22−10.3 (3)
C11—C9—C10—C19−61.0 (3)C20—C22—C23—C23'−3.5 (4)
C8—C9—C10—C1967.4 (3)C20—C22—C23—C24175.4 (3)
C11—C9—C10—C5177.7 (2)O22'—C22—C23—C23'179.3 (2)
C8—C9—C10—C5−53.9 (2)O22'—C22—C23—C24−1.8 (4)
C8—C9—C11—C1252.6 (3)C22—C23—C23'—O23"−12.3 (4)
C10—C9—C11—C12−178.2 (2)C24—C23—C23'—O23"168.8 (3)
C9—C11—C12—C13−53.4 (3)C22—C23—C23'—C23"167.7 (3)
C11—C12—C13—C1453.4 (3)C24—C23—C23'—C23"−11.2 (4)
C11—C12—C13—C17163.7 (2)C22—C23—C24—C2579.4 (4)
C11—C12—C13—C18−68.9 (3)C23'—C23—C24—C25−101.7 (4)
C7—C8—C14—C15−51.6 (3)C23—C24—C25—C26B22.1 (8)
C9—C8—C14—C15−175.1 (2)C23—C24—C25—C27−168.3 (3)
C7—C8—C14—C13−177.1 (2)C23—C24—C25—C26A80.1 (7)
C9—C8—C14—C1359.5 (2)C26B—C25—C26A—O26A50.6 (11)
C12—C13—C14—C15167.2 (2)C24—C25—C26A—O26A−69.2 (12)
C17—C13—C14—C1546.6 (2)C27—C25—C26A—O26A173.3 (9)
C18—C13—C14—C15−72.1 (3)C24—C25—C26B—O26B85.8 (11)
C12—C13—C14—C8−59.3 (3)C27—C25—C26B—O26B−82.5 (11)
C17—C13—C14—C8−179.86 (19)C26A—C25—C26B—O26B−2.6 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3'—H3'···O23"i0.981.892.841 (3)163
O26A—H26E···O3'ii0.822.202.951 (6)153
O26B—H26F···O3'ii0.822.242.919 (16)140

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2197).

References

  • Meza-Reyes, S., Montiel-Smith, S., Sandoval-Ramírez, J., Bernès, S., Hernández-Linares, G., Santillan, R. L. & Rincón, S. (2004). Acta Cryst. E60, o1137–o1139.
  • Sandoval-Ramírez, J., Meza-Reyes, S., Montiel-Smith, S., Bernès, S., Hernández-Linares, G. & Bravo, O. V. (2003). Acta Cryst. E59, o1817–o1819.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). XSCANS Version 2.21. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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