Fern-9(11)-en-6α-ol–methanol (1/1)

Bhattacharyya, K.; Kar, T.; Bocelli, G.; Righi, L.; Venkateswarlu, Y.; Reddy, V.L.N.

doi:10.1107/S1600536801002215

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Fern-9(11)-en-6α-ol–methanol (1/1)

K. Bhattacharyya, T. Kar, G. Bocelli, L. Righi, Y. Venkateswarlu and V. L. N. Reddy

The title compound, C₃₀H₅₀O·CH₄O, is a triterpenoid. It consists of four six-membered rings and one five-membered ring. Of the four six-membered rings, two adopt the chair conformation, one is in the twist-boat conformation and the one containing a double bond is in a distorted chair conformation with distortion towards the boat conformation. The five-membered ring adopts the pure envelope conformation. There is a hydrogen bond between the O atom of the hydroxyl group at C6 and the O atom of the solvent molecule, but no other intermolecular hydrogen bonds exist in the structure, so it is stabilized by van der Waals interactions only.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801002215/cf6036sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801002215/cf6036Isup2.hkl Contains datablock I

CCDC reference: 159852

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.052
wR factor = 0.158
Data-to-parameter ratio = 9.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           70.01
         From the CIF: _reflns_number_total               2865
         Count of symmetry unique reflns         2867
         Completeness (_total/calc)             99.93%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

Comment top

The title compound, (I), has been isolated from the whole plant of Adiantum lunuatum L. (Adiantaceae) which is a common fern and used as an ornamental plant in Japan, Europe and widely distributed in India. The dried whole plant has been used as a medicine for bronchitis and cough (Hashimoto & Nishimoto, 1996). Isolation of this compound has also been reported by another group (Sunder et al., 1976). Spectroscopic analysis suggest that the compound is closely related to a derivative of fern-9(11)-ene, but there is an ambiguity regarding the position of the hydroxyl group which is located at C6. So to establish the structure unequivocally the present X-ray structural analysis of the title compound has been undertaken, which confirms the structure obtained by chemical and spectroscopic studies.

The data set does not contain any Friedel opposites, and the value of the Flack (1983) parameter obtained is inadequate to indicate the absolute configuration. However, the absolute stereochemistry of a related triterpenoid has been established by Oh & Maslen (1966) by a direct method of anomalous dispersion phasing and the present structure is in accord with this. Hence the present enantiomer has been retained.

The molecule is composed of five fused rings, four of which are six-membered and one is five-membered. Rings A (C1–C5/C10) and D (C13–C18) adopt a chair conformation (see Table 2), ring B (C5–C9/C10) is in a twist boat conformation, ring C (C8–C14) containing a double bond is in a distorted chair conformation and the five-membered ring E (C17–C21) adopts an envelope conformation. The conformation of a chair in ring A followed by a boat in ring B is unusual but also observed in the pentacyclo triterpenoid (Parvez et al., 1999). This configuration seems to have arisen from the coplanarity of atoms C8–C12 due to the double bond at C9═C11. The relevant torsion angles are C8—C9—-C11–C12 - 0.3 (5)° and C10—C9—C11—C12 177.4 (3)°. In ring C, atoms C8, C9, C13 and C14 are only approximately coplanar, with deviations of up to 0.238 (3) Å from their mean plane. Atom C8 is 0.526 (3) Å above this plane and atom C12 is 0.481 (3) Å below it. Hence it is inferred that the conformation of ring C is intermediate between a chair and a twist boat, with a ring puckering parameter ϕ = 95.1 (4)°. The ring-puckering parameters (Table 2) were calculated using the method of Cremer & Pople (1975). The hydroxyl group at C6 is twisted from the plane of the ring B. The associated torsion angles are C10—C5—C6—O1 - 143.6 (2)° and C8—C7—C6—O1 81.4 (3)°.

The Csp³—Csp³ bond lengths lie between 1.519 (6) and 1.571 (4) Å. The variation in bond length indicates that the structure is subject to certain strain which mainly arises from the repulsion of the methyl groups at C25 and C27 and also from the constraint placed on C8–C12 to lie in one plane due to the presence of a double bond at C9═C11. Repulsion between two methyl groups C25 and C27 is evident in that the angles C18—C13—C25 112.3 (2)° and C18—C17—C27 115.3 (2)° are much larger than the normal tetrahedral value of 109.5° formed by pairs of Csp³—Csp³ bonds. Csp³—Csp² bond lengths lie between 1.502 (5) and 1.546 (3) Å. In the molecule (Fig. 1), there is one endocyclic double bond C9═C11 and one Csp³—O bond, indicated by the bond lengths 1.331 (4) and 1.451 (3) Å, respectively. All these values are within expected ranges.

The O1S atom of the methanol solvent molecule is connected to the main molecule through a hydrogen bond with the O atom of the hydroxyl group: O1S—H1OS····O1, with O1S···O1 2.781 (4) Å and O1S—H1OS···O1 173.2 (2)°. There are no other intermolecular hydrogen bonds and the structure is stabilized by van der Waals interactions.

Experimental top

The shade-dried and powdered whole plant (1.25 kg) of Adiantum Lunulatum was extracted with hexane (3 x 5L) followed by CH₂Cl₂:MeOH (1:1) (3 x 5L) at room temperature. The combined hexane extract was filtered and concentrated under pressure to obtain a greenish gummy residue (16.41 g). Silica gel column chromatography by gradient elution using hexane through hexane/benzene mixtures to benzene afforded the compound fern-9(11)-en-6α-ol (120 mg). Crystals of the title compound were then obtained from a solution in methanol by slow evaporation at room temperature. The extraction procedure is described by Niranjan Reddy et al. (2001).

Computing details top

Data collection: local program (Belletti, 1992); cell refinement: local program; data reduction: local program; program(s) used to solve structure: SIR97 (Cascarano et al., 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai & Huttner, 1994); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

fern-9(11)-en-6α-ol–methanol (1/1) top

Crystal data top

C₃₀H₄₉OH·CH₄O	F(000) = 512
M_r = 458.74	D_x = 1.083 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
a = 11.505 (3) Å	Cell parameters from 39 reflections
b = 8.484 (2) Å	θ = 11.1–36.7°
c = 14.616 (4) Å	µ = 0.49 mm⁻¹
β = 99.42 (3)°	T = 293 K
V = 1407.4 (6) Å³	Plate, colourless
Z = 2	0.19 × 0.14 × 0.11 mm

Data collection top

Siemens AED single-crystal diffractometer	2600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 70.0°, θ_min = 3.1°
ω–2θ scans	h = −14→13
Absorption correction: part of the refinement model (ΔF) DIFABS (Walker & Stuart, 1983) and Gluzinski (1989)	k = −10→2
T_min = 0.92, T_max = 0.95	l = 0→17
5337 measured reflections	2 standard reflections every 100 reflections
2865 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: geom & circular difference map
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.1072P)² + 0.1153P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.158	(Δ/σ)_max = 0.007
S = 1.12	Δρ_max = 0.18 e Å⁻³
2865 reflections	Δρ_min = −0.18 e Å⁻³
310 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0116 (17)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (4)

Crystal data top

C₃₀H₄₉OH·CH₄O	V = 1407.4 (6) Å³
M_r = 458.74	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 11.505 (3) Å	µ = 0.49 mm⁻¹
b = 8.484 (2) Å	T = 293 K
c = 14.616 (4) Å	0.19 × 0.14 × 0.11 mm
β = 99.42 (3)°

Data collection top

Siemens AED single-crystal diffractometer	2600 reflections with I > 2σ(I)
Absorption correction: part of the refinement model (ΔF) DIFABS (Walker & Stuart, 1983) and Gluzinski (1989)	R_int = 0.032
T_min = 0.92, T_max = 0.95	2 standard reflections every 100 reflections
5337 measured reflections	intensity decay: none
2865 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.158	Δρ_max = 0.18 e Å⁻³
S = 1.12	Δρ_min = −0.18 e Å⁻³
2865 reflections	Absolute structure: Flack (1983)
310 parameters	Absolute structure parameter: 0.0 (4)
1 restraint

Special details top

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

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

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

	x	y	z	U_iso*/U_eq
C1	−0.3617 (3)	−0.1508 (5)	0.7496 (3)	0.0689 (9)
H1A	−0.3676	−0.1309	0.8140	0.083*
H1B	−0.3653	−0.0498	0.7181	0.083*
C2	−0.4672 (3)	−0.2504 (6)	0.7062 (3)	0.0830 (12)
H2A	−0.4680	−0.3485	0.7402	0.100*
H2B	−0.5397	−0.1943	0.7101	0.100*
C3	−0.4603 (3)	−0.2856 (6)	0.6053 (3)	0.0751 (9)
H3A	−0.4642	−0.1871	0.5712	0.090*
H3B	−0.5280	−0.3485	0.5791	0.090*
C4	−0.3469 (3)	−0.3740 (4)	0.5925 (2)	0.0568 (7)
C5	−0.2388 (2)	−0.2754 (3)	0.64152 (17)	0.0465 (5)
H5	−0.2451	−0.1748	0.6081	0.056*
C6	−0.1190 (2)	−0.3430 (3)	0.62643 (17)	0.0461 (6)
H6	−0.1232	−0.4584	0.6258	0.055*
C7	−0.0171 (2)	−0.2906 (3)	0.69980 (18)	0.0479 (6)
H7A	0.0563	−0.3008	0.6757	0.058*
H7B	−0.0126	−0.3579	0.7539	0.058*
C8	−0.0336 (2)	−0.1194 (3)	0.72759 (17)	0.0420 (5)
H8	−0.0511	−0.0588	0.6699	0.050*
C9	−0.1417 (2)	−0.1077 (3)	0.77483 (18)	0.0476 (6)
C10	−0.2414 (2)	−0.2283 (4)	0.7448 (2)	0.0509 (6)
C11	−0.1469 (3)	−0.0013 (4)	0.8409 (2)	0.0584 (7)
H11	−0.2151	0.0011	0.8674	0.070*
C12	−0.0519 (3)	0.1152 (4)	0.87646 (19)	0.0580 (7)
H12A	−0.0135	0.0830	0.9377	0.070*
H12B	−0.0872	0.2178	0.8822	0.070*
C13	0.0410 (2)	0.1287 (3)	0.81198 (16)	0.0433 (5)
C14	0.0761 (2)	−0.0419 (3)	0.78627 (16)	0.0417 (5)
C15	0.1790 (2)	−0.0323 (3)	0.73083 (19)	0.0497 (6)
H15A	0.2014	−0.1384	0.7162	0.060*
H15B	0.1519	0.0215	0.6727	0.060*
C16	0.2885 (2)	0.0538 (3)	0.7819 (2)	0.0511 (6)
H16A	0.3212	−0.0062	0.8366	0.061*
H16B	0.3476	0.0589	0.7417	0.061*
C17	0.2605 (2)	0.2209 (3)	0.81106 (15)	0.0444 (5)
C18	0.1522 (2)	0.2110 (3)	0.86228 (16)	0.0446 (5)
H18	0.1790	0.1430	0.9158	0.053*
C19	0.1457 (3)	0.3761 (4)	0.9047 (2)	0.0566 (7)
H19A	0.1085	0.3722	0.9596	0.068*
H19B	0.1023	0.4484	0.8603	0.068*
C20	0.2764 (3)	0.4250 (4)	0.9294 (2)	0.0601 (7)
H20A	0.2990	0.4339	0.9961	0.072*
H20B	0.2889	0.5262	0.9017	0.072*
C21	0.3507 (2)	0.2958 (3)	0.89094 (18)	0.0482 (6)
H21	0.3674	0.2154	0.9394	0.058*
C22	−0.3514 (4)	−0.5441 (5)	0.6266 (3)	0.0721 (9)
H22A	−0.4111	−0.6011	0.5861	0.108*
H22B	−0.3697	−0.5444	0.6883	0.108*
H22C	−0.2763	−0.5935	0.6266	0.108*
C23	−0.3455 (3)	−0.3809 (6)	0.4869 (2)	0.0781 (11)
H23A	−0.2826	−0.4484	0.4751	0.117*
H23B	−0.3338	−0.2769	0.4643	0.117*
H23C	−0.4193	−0.4219	0.4558	0.117*
C24	−0.2246 (3)	−0.3676 (5)	0.8148 (2)	0.0692 (9)
H24A	−0.2043	−0.3271	0.8767	0.104*
H24B	−0.1626	−0.4350	0.8012	0.104*
H24C	−0.2965	−0.4266	0.8097	0.104*
C25	−0.0186 (3)	0.2222 (4)	0.7261 (2)	0.0539 (6)
H25A	−0.0136	0.3330	0.7395	0.081*
H25B	−0.0998	0.1918	0.7111	0.081*
H25C	0.0207	0.1999	0.6745	0.081*
C26	0.1145 (3)	−0.1457 (4)	0.8732 (2)	0.0565 (7)
H26A	0.1482	−0.2421	0.8552	0.085*
H26B	0.0472	−0.1691	0.9019	0.085*
H26C	0.1720	−0.0901	0.9164	0.085*
C27	0.2460 (3)	0.3322 (4)	0.7265 (2)	0.0608 (7)
H27A	0.3216	0.3511	0.7089	0.091*
H27B	0.2128	0.4303	0.7423	0.091*
H27C	0.1946	0.2843	0.6757	0.091*
C28	0.4705 (3)	0.3566 (4)	0.8728 (2)	0.0579 (7)
H28	0.4567	0.4455	0.8296	0.069*
C29	0.5428 (3)	0.2333 (5)	0.8313 (3)	0.0708 (9)
H29A	0.5496	0.1403	0.8692	0.106*
H29B	0.6198	0.2745	0.8287	0.106*
H29C	0.5044	0.2073	0.7698	0.106*
C30	0.5420 (4)	0.4158 (6)	0.9631 (3)	0.0868 (13)
H30A	0.5418	0.3376	1.0106	0.130*
H30B	0.5078	0.5116	0.9815	0.130*
H30C	0.6216	0.4356	0.9543	0.130*
O1	−0.09827 (17)	−0.2879 (3)	0.53654 (13)	0.0531 (5)
H1O1	−0.0404	−0.3328	0.5228	0.080*
O1S	−0.0913 (2)	0.0284 (3)	0.48765 (19)	0.0713 (6)
H1OS	−0.0946	−0.0624	0.5063	0.107*
C1S	−0.2020 (3)	0.0982 (6)	0.4806 (3)	0.0792 (10)
H1CS	−0.2308	0.0865	0.5382	0.119*
H2CS	−0.2555	0.0481	0.4319	0.119*
H3CS	−0.1961	0.2083	0.4667	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0550 (15)	0.070 (2)	0.087 (2)	−0.0005 (16)	0.0260 (15)	−0.0120 (19)
C2	0.0519 (16)	0.086 (3)	0.117 (3)	−0.0080 (17)	0.0305 (18)	−0.019 (2)
C3	0.0469 (15)	0.081 (2)	0.095 (2)	−0.0022 (17)	0.0061 (14)	−0.001 (2)
C4	0.0508 (14)	0.0614 (17)	0.0573 (14)	−0.0064 (13)	0.0057 (11)	−0.0006 (13)
C5	0.0474 (12)	0.0419 (12)	0.0501 (12)	−0.0012 (11)	0.0073 (10)	0.0034 (11)
C6	0.0530 (13)	0.0348 (12)	0.0502 (12)	0.0011 (10)	0.0076 (10)	−0.0026 (10)
C7	0.0481 (12)	0.0399 (13)	0.0543 (13)	0.0073 (11)	0.0041 (10)	−0.0062 (11)
C8	0.0460 (12)	0.0373 (12)	0.0423 (11)	0.0063 (9)	0.0063 (9)	−0.0016 (9)
C9	0.0481 (12)	0.0476 (14)	0.0482 (12)	0.0039 (11)	0.0115 (10)	0.0011 (11)
C10	0.0516 (13)	0.0481 (14)	0.0557 (14)	0.0006 (11)	0.0162 (11)	0.0026 (12)
C11	0.0574 (15)	0.0653 (19)	0.0567 (14)	0.0025 (14)	0.0214 (12)	−0.0058 (14)
C12	0.0629 (16)	0.0605 (17)	0.0540 (14)	0.0017 (14)	0.0192 (12)	−0.0147 (14)
C13	0.0547 (13)	0.0366 (12)	0.0386 (11)	0.0070 (10)	0.0076 (9)	−0.0038 (9)
C14	0.0484 (12)	0.0363 (12)	0.0400 (11)	0.0064 (10)	0.0060 (9)	0.0002 (9)
C15	0.0498 (13)	0.0468 (14)	0.0531 (13)	0.0048 (11)	0.0099 (10)	−0.0120 (11)
C16	0.0503 (13)	0.0444 (14)	0.0588 (14)	0.0019 (11)	0.0097 (11)	−0.0094 (12)
C17	0.0568 (13)	0.0393 (12)	0.0365 (10)	0.0011 (11)	0.0058 (9)	−0.0006 (10)
C18	0.0551 (13)	0.0379 (12)	0.0401 (11)	0.0053 (11)	0.0062 (10)	−0.0007 (10)
C19	0.0660 (16)	0.0466 (15)	0.0562 (15)	0.0046 (13)	0.0067 (12)	−0.0125 (13)
C20	0.0722 (18)	0.0480 (16)	0.0595 (15)	0.0003 (14)	0.0088 (13)	−0.0126 (13)
C21	0.0579 (14)	0.0405 (13)	0.0449 (12)	−0.0023 (12)	0.0047 (10)	−0.0029 (10)
C22	0.080 (2)	0.0569 (19)	0.079 (2)	−0.0194 (17)	0.0111 (17)	−0.0040 (17)
C23	0.0718 (19)	0.101 (3)	0.0572 (16)	−0.025 (2)	−0.0027 (14)	−0.0012 (18)
C24	0.089 (2)	0.0635 (19)	0.0564 (16)	−0.0136 (18)	0.0163 (15)	0.0111 (15)
C25	0.0592 (14)	0.0413 (13)	0.0569 (14)	0.0096 (12)	−0.0034 (11)	0.0018 (12)
C26	0.0673 (16)	0.0434 (14)	0.0535 (15)	0.0005 (13)	−0.0060 (12)	0.0073 (12)
C27	0.0758 (18)	0.0571 (17)	0.0489 (14)	−0.0038 (15)	0.0080 (13)	0.0061 (14)
C28	0.0672 (16)	0.0490 (15)	0.0572 (15)	−0.0097 (14)	0.0095 (12)	−0.0025 (13)
C29	0.0656 (18)	0.064 (2)	0.086 (2)	−0.0092 (16)	0.0228 (16)	−0.0096 (18)
C30	0.077 (2)	0.099 (3)	0.082 (2)	−0.028 (2)	0.0068 (18)	−0.030 (2)
O1	0.0544 (10)	0.0558 (11)	0.0504 (9)	0.0038 (9)	0.0124 (7)	−0.0020 (9)
O1S	0.0659 (12)	0.0654 (14)	0.0843 (15)	−0.0051 (11)	0.0171 (10)	0.0182 (13)
C1S	0.084 (2)	0.072 (2)	0.085 (2)	0.009 (2)	0.0213 (18)	0.008 (2)

Geometric parameters (Å, º) top

C1—C2	1.529 (5)	C17—C18	1.558 (3)
C1—C10	1.545 (4)	C17—C21	1.564 (3)
C1—H1A	0.970	C18—C19	1.539 (4)
C1—H1B	0.970	C18—H18	0.980
C2—C3	1.519 (6)	C19—C20	1.545 (4)
C2—H2A	0.970	C19—H19A	0.970
C2—H2B	0.970	C19—H19B	0.970
C3—C4	1.544 (5)	C20—C21	1.551 (4)
C3—H3A	0.970	C20—H20A	0.970
C3—H3B	0.970	C20—H20B	0.970
C4—C22	1.531 (5)	C21—C28	1.535 (4)
C4—C23	1.547 (4)	C21—H21	0.980
C4—C5	1.571 (4)	C22—H22A	0.960
C5—C6	1.541 (4)	C22—H22B	0.960
C5—C10	1.567 (4)	C22—H22C	0.960
C5—H5	0.980	C23—H23A	0.960
C6—O1	1.451 (3)	C23—H23B	0.960
C6—C7	1.521 (3)	C23—H23C	0.960
C6—H6	0.980	C24—H24A	0.960
C7—C8	1.528 (4)	C24—H24B	0.960
C7—H7A	0.970	C24—H24C	0.960
C7—H7B	0.970	C25—H25A	0.960
C8—C9	1.522 (3)	C25—H25B	0.960
C8—C14	1.551 (3)	C25—H25C	0.960
C8—H8	0.980	C26—H26A	0.960
C9—C11	1.331 (4)	C26—H26B	0.960
C9—C10	1.545 (4)	C26—H26C	0.960
C10—C24	1.554 (4)	C27—H27A	0.960
C11—C12	1.502 (5)	C27—H27B	0.960
C11—H11	0.930	C27—H27C	0.960
C12—C13	1.540 (4)	C28—C29	1.522 (5)
C12—H12A	0.970	C28—C30	1.522 (5)
C12—H12B	0.970	C28—H28	0.980
C13—C18	1.535 (4)	C29—H29A	0.960
C13—C25	1.547 (4)	C29—H29B	0.960
C13—C14	1.565 (3)	C29—H29C	0.960
C14—C15	1.542 (4)	C30—H30A	0.960
C14—C26	1.550 (3)	C30—H30B	0.960
C15—C16	1.539 (4)	C30—H30C	0.960
C15—H15A	0.970	O1—H1O1	0.820
C15—H15B	0.970	O1S—C1S	1.393 (5)
C16—C17	1.530 (4)	O1S—H1OS	0.820
C16—H16A	0.970	C1S—H1CS	0.960
C16—H16B	0.970	C1S—H2CS	0.960
C17—C27	1.542 (4)	C1S—H3CS	0.960

C2—C1—C10	113.7 (3)	C16—C17—C18	107.7 (2)
C2—C1—H1A	108.8	C27—C17—C18	115.3 (2)
C10—C1—H1A	108.8	C16—C17—C21	116.1 (2)
C2—C1—H1B	108.8	C27—C17—C21	108.7 (2)
C10—C1—H1B	108.8	C18—C17—C21	98.54 (18)
H1A—C1—H1B	107.7	C13—C18—C19	121.0 (2)
C3—C2—C1	110.3 (3)	C13—C18—C17	117.7 (2)
C3—C2—H2A	109.6	C19—C18—C17	103.9 (2)
C1—C2—H2A	109.6	C13—C18—H18	104.1
C3—C2—H2B	109.6	C19—C18—H18	104.1
C1—C2—H2B	109.6	C17—C18—H18	104.1
H2A—C2—H2B	108.1	C18—C19—C20	103.2 (2)
C2—C3—C4	113.1 (3)	C18—C19—H19A	111.1
C2—C3—H3A	109.0	C20—C19—H19A	111.1
C4—C3—H3A	109.0	C18—C19—H19B	111.1
C2—C3—H3B	109.0	C20—C19—H19B	111.1
C4—C3—H3B	109.0	H19A—C19—H19B	109.1
H3A—C3—H3B	107.8	C19—C20—C21	107.4 (2)
C22—C4—C3	110.1 (3)	C19—C20—H20A	110.2
C22—C4—C23	107.2 (3)	C21—C20—H20A	110.2
C3—C4—C23	106.6 (3)	C19—C20—H20B	110.2
C22—C4—C5	114.9 (3)	C21—C20—H20B	110.2
C3—C4—C5	107.9 (3)	H20A—C20—H20B	108.5
C23—C4—C5	109.8 (3)	C28—C21—C20	112.9 (2)
C6—C5—C10	113.0 (2)	C28—C21—C17	120.8 (2)
C6—C5—C4	113.3 (2)	C20—C21—C17	102.7 (2)
C10—C5—C4	115.9 (2)	C28—C21—H21	106.5
C6—C5—H5	104.3	C20—C21—H21	106.5
C10—C5—H5	104.3	C17—C21—H21	106.5
C4—C5—H5	104.3	C4—C22—H22A	109.5
O1—C6—C7	108.8 (2)	C4—C22—H22B	109.5
O1—C6—C5	107.0 (2)	H22A—C22—H22B	109.5
C7—C6—C5	113.2 (2)	C4—C22—H22C	109.5
O1—C6—H6	109.2	H22A—C22—H22C	109.5
C7—C6—H6	109.2	H22B—C22—H22C	109.5
C5—C6—H6	109.2	C4—C23—H23A	109.5
C6—C7—C8	110.5 (2)	C4—C23—H23B	109.5
C6—C7—H7A	109.5	H23A—C23—H23B	109.5
C8—C7—H7A	109.5	C4—C23—H23C	109.5
C6—C7—H7B	109.5	H23A—C23—H23C	109.5
C8—C7—H7B	109.5	H23B—C23—H23C	109.5
H7A—C7—H7B	108.1	C10—C24—H24A	109.5
C9—C8—C7	109.2 (2)	C10—C24—H24B	109.5
C9—C8—C14	111.9 (2)	H24A—C24—H24B	109.5
C7—C8—C14	115.1 (2)	C10—C24—H24C	109.5
C9—C8—H8	106.7	H24A—C24—H24C	109.5
C7—C8—H8	106.7	H24B—C24—H24C	109.5
C14—C8—H8	106.7	C13—C25—H25A	109.5
C11—C9—C8	120.7 (2)	C13—C25—H25B	109.5
C11—C9—C10	122.4 (2)	H25A—C25—H25B	109.5
C8—C9—C10	116.9 (2)	C13—C25—H25C	109.5
C1—C10—C9	109.5 (3)	H25A—C25—H25C	109.5
C1—C10—C24	108.1 (3)	H25B—C25—H25C	109.5
C9—C10—C24	108.1 (2)	C14—C26—H26A	109.5
C1—C10—C5	108.1 (2)	C14—C26—H26B	109.5
C9—C10—C5	108.2 (2)	H26A—C26—H26B	109.5
C24—C10—C5	114.9 (3)	C14—C26—H26C	109.5
C9—C11—C12	125.5 (2)	H26A—C26—H26C	109.5
C9—C11—H11	117.2	H26B—C26—H26C	109.5
C12—C11—H11	117.2	C17—C27—H27A	109.5
C11—C12—C13	112.1 (2)	C17—C27—H27B	109.5
C11—C12—H12A	109.2	H27A—C27—H27B	109.5
C13—C12—H12A	109.2	C17—C27—H27C	109.5
C11—C12—H12B	109.2	H27A—C27—H27C	109.5
C13—C12—H12B	109.2	H27B—C27—H27C	109.5
H12A—C12—H12B	107.9	C29—C28—C30	108.7 (3)
C18—C13—C12	110.4 (2)	C29—C28—C21	113.7 (3)
C18—C13—C25	112.3 (2)	C30—C28—C21	109.5 (3)
C12—C13—C25	106.0 (2)	C29—C28—H28	108.3
C18—C13—C14	107.93 (19)	C30—C28—H28	108.3
C12—C13—C14	108.1 (2)	C21—C28—H28	108.3
C25—C13—C14	112.2 (2)	C28—C29—H29A	109.5
C15—C14—C26	108.7 (2)	C28—C29—H29B	109.5
C15—C14—C8	110.91 (19)	H29A—C29—H29B	109.5
C26—C14—C8	108.0 (2)	C28—C29—H29C	109.5
C15—C14—C13	109.1 (2)	H29A—C29—H29C	109.5
C26—C14—C13	112.3 (2)	H29B—C29—H29C	109.5
C8—C14—C13	107.84 (19)	C28—C30—H30A	109.5
C16—C15—C14	114.1 (2)	C28—C30—H30B	109.5
C16—C15—H15A	108.7	H30A—C30—H30B	109.5
C14—C15—H15A	108.7	C28—C30—H30C	109.5
C16—C15—H15B	108.7	H30A—C30—H30C	109.5
C14—C15—H15B	108.7	H30B—C30—H30C	109.5
H15A—C15—H15B	107.6	C6—O1—H1O1	109.5
C17—C16—C15	112.5 (2)	C1S—O1S—H1OS	109.5
C17—C16—H16A	109.1	O1S—C1S—H1CS	109.5
C15—C16—H16A	109.1	O1S—C1S—H2CS	109.5
C17—C16—H16B	109.1	H1CS—C1S—H2CS	109.5
C15—C16—H16B	109.1	O1S—C1S—H3CS	109.5
H16A—C16—H16B	107.8	H1CS—C1S—H3CS	109.5
C16—C17—C27	110.1 (2)	H2CS—C1S—H3CS	109.5

C10—C1—C2—C3	−57.9 (5)	C7—C8—C14—C26	−55.7 (3)
C1—C2—C3—C4	58.8 (5)	C9—C8—C14—C13	−51.8 (3)
C2—C3—C4—C22	71.3 (4)	C7—C8—C14—C13	−177.3 (2)
C2—C3—C4—C23	−172.7 (4)	C18—C13—C14—C15	−54.3 (2)
C2—C3—C4—C5	−54.7 (4)	C12—C13—C14—C15	−173.7 (2)
C22—C4—C5—C6	62.0 (3)	C25—C13—C14—C15	69.9 (3)
C3—C4—C5—C6	−174.8 (3)	C18—C13—C14—C26	66.3 (3)
C23—C4—C5—C6	−58.9 (4)	C12—C13—C14—C26	−53.1 (3)
C22—C4—C5—C10	−71.1 (3)	C25—C13—C14—C26	−169.5 (2)
C3—C4—C5—C10	52.2 (3)	C18—C13—C14—C8	−174.86 (19)
C23—C4—C5—C10	168.0 (3)	C12—C13—C14—C8	65.8 (2)
C10—C5—C6—O1	−143.6 (2)	C25—C13—C14—C8	−50.7 (3)
C4—C5—C6—O1	82.0 (3)	C26—C14—C15—C16	−65.4 (3)
C10—C5—C6—C7	−23.7 (3)	C8—C14—C15—C16	176.0 (2)
C4—C5—C6—C7	−158.1 (2)	C13—C14—C15—C16	57.3 (3)
O1—C6—C7—C8	81.4 (3)	C14—C15—C16—C17	−56.3 (3)
C5—C6—C7—C8	−37.5 (3)	C15—C16—C17—C27	−76.5 (3)
C6—C7—C8—C9	65.3 (3)	C15—C16—C17—C18	50.1 (3)
C6—C7—C8—C14	−167.9 (2)	C15—C16—C17—C21	159.4 (2)
C7—C8—C9—C11	148.4 (3)	C12—C13—C18—C19	−56.6 (3)
C14—C8—C9—C11	19.8 (4)	C25—C13—C18—C19	61.4 (3)
C7—C8—C9—C10	−29.4 (3)	C14—C13—C18—C19	−174.5 (2)
C14—C8—C9—C10	−158.0 (2)	C12—C13—C18—C17	174.3 (2)
C2—C1—C10—C9	170.4 (3)	C25—C13—C18—C17	−67.7 (3)
C2—C1—C10—C24	−72.1 (4)	C14—C13—C18—C17	56.4 (3)
C2—C1—C10—C5	52.8 (4)	C16—C17—C18—C13	−53.7 (3)
C11—C9—C10—C1	35.6 (4)	C27—C17—C18—C13	69.8 (3)
C8—C9—C10—C1	−146.7 (3)	C21—C17—C18—C13	−174.7 (2)
C11—C9—C10—C24	−81.9 (4)	C16—C17—C18—C19	169.5 (2)
C8—C9—C10—C24	95.8 (3)	C27—C17—C18—C19	−67.0 (3)
C11—C9—C10—C5	153.1 (3)	C21—C17—C18—C19	48.5 (2)
C8—C9—C10—C5	−29.1 (3)	C13—C18—C19—C20	−169.1 (2)
C6—C5—C10—C1	175.7 (2)	C17—C18—C19—C20	−34.1 (3)
C4—C5—C10—C1	−51.1 (3)	C18—C19—C20—C21	5.9 (3)
C6—C5—C10—C9	57.2 (3)	C19—C20—C21—C28	155.7 (2)
C4—C5—C10—C9	−169.6 (2)	C19—C20—C21—C17	24.0 (3)
C6—C5—C10—C24	−63.6 (3)	C16—C17—C21—C28	75.1 (3)
C4—C5—C10—C24	69.6 (3)	C27—C17—C21—C28	−49.7 (3)
C8—C9—C11—C12	−0.2 (5)	C18—C17—C21—C28	−170.2 (3)
C10—C9—C11—C12	177.4 (3)	C16—C17—C21—C20	−158.1 (2)
C9—C11—C12—C13	14.5 (5)	C27—C17—C21—C20	77.1 (3)
C11—C12—C13—C18	−164.3 (3)	C18—C17—C21—C20	−43.5 (3)
C11—C12—C13—C25	73.9 (3)	C20—C21—C28—C29	−177.6 (3)
C11—C12—C13—C14	−46.5 (3)	C17—C21—C28—C29	−55.6 (4)
C9—C8—C14—C15	−171.3 (2)	C20—C21—C28—C30	60.6 (4)
C7—C8—C14—C15	63.3 (3)	C17—C21—C28—C30	−177.4 (3)
C9—C8—C14—C26	69.7 (3)

Experimental details

Crystal data
Chemical formula	C₃₀H₄₉OH·CH₄O
M_r	458.74
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	11.505 (3), 8.484 (2), 14.616 (4)
β (°)	99.42 (3)
V (Å³)	1407.4 (6)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.19 × 0.14 × 0.11

Data collection
Diffractometer	Siemens AED single-crystal diffractometer
Absorption correction	Part of the refinement model (ΔF) DIFABS (Walker & Stuart, 1983) and Gluzinski (1989)
T_min, T_max	0.92, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	5337, 2865, 2600
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.158, 1.12
No. of reflections	2865
No. of parameters	310
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18
Absolute structure	Flack (1983)
Absolute structure parameter	0.0 (4)

Computer programs: local program (Belletti, 1992), local program, SIR97 (Cascarano et al., 1996), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai & Huttner, 1994), SHELXL97 and PARST (Nardelli, 1983).

Selected geometric parameters (Å, º) top

C6—O1	1.451 (3)	C9—C11	1.331 (4)

O1—C6—C7	108.8 (2)	C8—C9—C10	116.9 (2)
O1—C6—C5	107.0 (2)	C9—C11—C12	125.5 (2)
C11—C9—C8	120.7 (2)	C18—C13—C25	112.3 (2)
C11—C9—C10	122.4 (2)	C27—C17—C18	115.3 (2)

C10—C5—C6—O1	−143.6 (2)	C8—C9—C11—C12	−0.2 (5)
O1—C6—C7—C8	81.4 (3)	C10—C9—C11—C12	177.4 (3)

Ring-puckering parameters (Å, °) top

Ring	q₂	q₃	Q_T	θ
A	0.037 (4)	0.562 (4)	0.563 (4)	3.7 (4)
B	0.758 (3)	-0.027 (3)	0.758 (3)	92.0 (2)
C	0.417 (3)	-0.355 (3)	0.548 (3)	130.4 (3)
D	0.038 (3)	0.563 (3)	0.564 (3)	3.9 (3)
E	0.490 (3)

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