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Acta Cryst. (2008). E64, o613    [ doi:10.1107/S1600536808004509 ]

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

M.-G. Hernández Linares, J. Sandoval Ramírez, S. Meza Reyes, S. Montiel Smith and S. Bernès

Abstract top

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 [alpha] face of the A-E 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 [alpha] face, avoiding steric hindrance with the carbonyl O atom of the acetyl group. The furostene and acetyl functionalities form an [alpha],[beta]-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.

Comment top

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 A–E 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.

Related literature top

The diacetate of the title compound has been characterized by X-ray (Sandoval-Ramírez et al., 2003), 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).

Experimental top

(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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
(E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol top
Crystal data top
C29H46O4Dx = 1.136 Mg m−3
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 mm−1
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 top
Bruker P4
diffractometer		Rint = 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 top
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 Å−3
323 parametersΔρmin = −0.13 e Å−3
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)
Crystal data top
C29H46O4V = 2681.7 (5) Å3
Mr = 458.66Z = 4
Monoclinic, C2Mo Kα
a = 23.568 (2) ŵ = 0.07 mm−1
b = 7.8420 (9) ÅT = 296 (1) K
c = 14.7840 (14) Å0.65 × 0.35 × 0.32 mm
β = 101.046 (5)º
Data collection top
Bruker P4
diffractometer		Rint = 0.026
Absorption correction: none3 standard reflections
4351 measured reflections every 97 reflections
2559 independent reflections intensity decay: 1%
2121 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.097Δρmax = 0.13 e Å−3
S = 1.02Δρmin = −0.13 e Å−3
2559 reflectionsAbsolute structure: ?
323 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Selected geometric parameters (°) top
C20—C22—C23—C23'−3.5 (4)O22'—C22—C23—C23'179.3 (2)
C20—C22—C23—C24175.4 (3)O22'—C22—C23—C24−1.8 (4)
Table 2
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

This work was supported by CONACyT (grant 60397).

references
References top

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.

Siemens (1996). XSCANS. Version 2.21. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.