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In the title compound, 3,20-dihydroxycevan-6-one, C27H43NO3, all the six-membered rings have normal chair conformations except ring D, which exists in a twist-chair conformation. The five-membered ring C adopts an envelope conformation. An O—H...O hydrogen bond connects the mol­ecules into spirals, which run along the b-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100014499/de1149sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100014499/de1149Isup2.hkl
Contains datablock I

CCDC reference: 159988

Comment top

The title compound, (I), was first isolated from Fritillaria imperialis L. (Liliaceae). It has since been extracted from several other species of Fritillaria (Xu et al., 1990; Hu et al., 1993) and also named imperialine and kashmirine. The structure and relative stereochemistry have been established by spectroscopy. In the course of systematic screening for anti-cough agents, sipeimine was isolated from Fritillaria roylei Hooker. The present study reports the crystal structure of sipeimine. The relative stereochemistry and conformation of all the rings in the molecule and the hydrogen-bonding scheme are now clearly defined.

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The molecule (Fig. 1) is composed of five six-membered rings and one five-membered ring. The stereochemistry of the ring juncture is A/B trans, B/C trans, C/D cis, D/E cis and E/F trans. The configurations at the other chiral centres are: C3—OH and C20—Me are equatorial; C10—Me, C20—OH and C22—Me are axial. Molecular dimensions are unexceptional. The cyclohexane rings A, B, E and F have normal chair conformations with mean values of the torsion angles: 55 (4), 55 (5), 57 (5) and 54.9 (16)°, respectively (the torsion angle of the normal chair form of cyclohexane is 56°). Ring D exists in a twist chair form owing to the cis fusion with ring C and ring E. This is also indicated by the smaller torsion angle C13—C12—C14—C15 30.6 (3)° and C12—C14—C15—C16 - 44.3 (4)°. The five-membered ring C adopts an envelope conformation with C11 displaced by 0.683 (4) Å from the mean plane of the remaining four atoms. The model also reveals that the skeleton is twisted strongly at the D ring because of the presence of cis H-atoms H12,H14 and H13,H17; this results in an interplanar angle of 79.9 (1)° between the planes of the A,B,C and E,F ring atoms.

Details of hydrogen bonding are in Table 1. Molecules are linked into spirals along the b-direction (Fig. 2). There is also an intramolecular O—H···N hydrogen bond.

Related literature top

For related literature, see: Hu et al. (1993); Xu et al. (1990).

Experimental top

Dried bulbs (1 kg) of Fritillaria roylei Hooker were ground to a fine powder and mixed with 5% sodium carbonate solution and dried at room temperature. The powder was macerated with CH2Cl2 for three days, filtered and the solution extracted with 1% hydrochloric acid. The pH of the solution was adjusted to 9 with potassium carbonate solution and extracted with diethyl ether. The solution was condensed under reduced pressure to give a diethyl ether extract, which was separated on an aluminium oxide column chromatography using acetyl acetate: methanol: concentrated ammonia solution (20:1:1) as eluent to afford sipeimine (30 mg). The product was dissolved with methanol and chloroform (3:2) and stored at room temperature. Three days later, transparent prism crystals were obtained.

Refinement top

H atoms were visible in difference maps allowed for as riding atoms with O—H 0.82 Å, C—H 0.96 to 0.98 Å. With no atoms having significant anomalous dispersion contributions, Friedel reflections were merged before the final refinement and the relative stereochemistry is shown in the scheme and figures.

Computing details top

Data collection: SMART (Bruker, 1998a); cell refinement: SMART and SAINT (Bruker, 1998a); data reduction: XPREP in SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1998b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Molecular structure, relative stereochemistry and atomic numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of (I) shown in a projection along the crystallographic a axis. Intermolecular hydrogen bonds are shown as dashed lines.
3β,20β-dihydroxy-6-one-5α-cevanine top
Crystal data top
C27H43NO3F(000) = 472
Mr = 429.62Dx = 1.199 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.6185 (5) ÅCell parameters from 3905 reflections
b = 12.3948 (8) Åθ = 1.4–26.0°
c = 14.5069 (10) ŵ = 0.08 mm1
β = 90.822 (1)°T = 293 K
V = 1189.95 (14) Å3Prism, colourless
Z = 20.52 × 0.35 × 0.20 mm
Data collection top
Siemens SMART/CCD
diffractometer
1789 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 26.0°, θmin = 1.4°
ω scansh = 88
7280 measured reflectionsk = 1513
2455 independent reflectionsl = 1617
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0662P)2]
where P = (Fo2 + 2Fc2)/3
2455 reflections(Δ/σ)max < 0.001
285 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C27H43NO3V = 1189.95 (14) Å3
Mr = 429.62Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.6185 (5) ŵ = 0.08 mm1
b = 12.3948 (8) ÅT = 293 K
c = 14.5069 (10) Å0.52 × 0.35 × 0.20 mm
β = 90.822 (1)°
Data collection top
Siemens SMART/CCD
diffractometer
1789 reflections with I > 2σ(I)
7280 measured reflectionsRint = 0.032
2455 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.111H-atom parameters constrained
S = 0.99Δρmax = 0.16 e Å3
2455 reflectionsΔρmin = 0.18 e Å3
285 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*/Ueq
O10.6837 (6)0.7650 (3)0.78059 (17)0.1145 (12)
H10.71910.82070.80670.172*
O20.0921 (5)0.9253 (2)0.59128 (19)0.1042 (10)
O30.1456 (4)0.40336 (18)0.09243 (16)0.0795 (7)
H30.25770.42210.07510.119*
N10.2739 (3)0.5855 (2)0.00561 (14)0.0462 (6)
C10.6414 (5)0.6826 (3)0.53240 (19)0.0614 (9)
H1A0.66180.61150.50630.074*
H1B0.73090.73230.50140.074*
C20.6965 (5)0.6798 (4)0.6355 (2)0.0740 (11)
H2A0.61870.62350.66500.089*
H2B0.83840.66160.64270.089*
C30.6575 (6)0.7854 (4)0.6835 (2)0.0823 (12)
H3A0.75720.83880.66390.099*
C40.4469 (6)0.8279 (3)0.6636 (2)0.0722 (10)
H4A0.43490.90020.68860.087*
H4B0.34890.78240.69390.087*
C50.3998 (5)0.8306 (3)0.5601 (2)0.0591 (8)
H50.50640.87490.53320.071*
C60.2024 (6)0.8869 (3)0.5342 (2)0.0725 (10)
C70.1509 (6)0.8910 (3)0.4326 (2)0.0749 (10)
H7A0.24220.93990.40170.090*
H7B0.01410.91750.42360.090*
C80.1696 (4)0.7782 (2)0.39169 (19)0.0501 (7)
H80.07400.73280.42510.060*
C90.3800 (4)0.7311 (2)0.41165 (17)0.0437 (6)
H90.47840.78350.38900.052*
C100.4213 (4)0.7175 (2)0.51475 (18)0.0458 (7)
C110.3838 (4)0.6352 (2)0.34595 (17)0.0442 (6)
H11A0.29670.57740.36680.053*
H11B0.51990.60760.33870.053*
C120.3029 (4)0.6862 (2)0.25628 (17)0.0438 (6)
H120.40870.73530.23510.053*
C130.2594 (4)0.6081 (2)0.17582 (16)0.0440 (6)
H130.35030.54630.18390.053*
C140.1264 (4)0.7587 (2)0.28844 (19)0.0503 (7)
H140.13060.82770.25550.060*
C150.0821 (4)0.7082 (3)0.2756 (2)0.0668 (9)
H15A0.10250.65550.32400.080*
H15B0.18380.76390.28220.080*
C160.1116 (5)0.6539 (3)0.1835 (2)0.0630 (9)
H16A0.09540.70630.13450.076*
H16B0.24710.62450.17890.076*
C170.0430 (4)0.5635 (2)0.17314 (18)0.0490 (7)
H170.02930.51600.22670.059*
C180.3075 (4)0.6586 (3)0.08329 (18)0.0501 (7)
H18A0.22420.72230.07460.060*
H18B0.44760.68160.08400.060*
C190.2773 (5)0.6351 (2)0.5569 (2)0.0544 (7)
H19A0.14060.65990.54950.082*
H19B0.30850.62690.62140.082*
H19C0.29240.56690.52640.082*
C200.0089 (5)0.4937 (2)0.0870 (2)0.0569 (8)
C210.2041 (7)0.4472 (4)0.0837 (3)0.0983 (15)
H21A0.21080.39020.03890.147*
H21B0.29840.50290.06680.147*
H21C0.23740.41910.14320.147*
C220.0597 (4)0.5548 (3)0.00137 (19)0.0490 (7)
H220.02240.62050.00450.059*
C230.0190 (5)0.4881 (3)0.0879 (2)0.0660 (9)
H23A0.08600.41880.08170.079*
H23B0.12500.47490.09400.079*
C240.0930 (5)0.5442 (3)0.17424 (19)0.0671 (9)
H24A0.07080.49770.22720.081*
H24B0.01680.61010.18410.081*
C250.3144 (6)0.5704 (3)0.1651 (2)0.0708 (10)
H250.34900.61630.21760.085*
C260.3466 (6)0.6372 (3)0.0786 (2)0.0745 (11)
H26A0.48980.65200.07120.089*
H26B0.27780.70580.08650.089*
C270.4472 (7)0.4725 (5)0.1692 (3)0.1074 (17)
H27A0.42630.42880.11550.161*
H27B0.58620.49450.17110.161*
H27C0.41420.43160.22350.161*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.158 (3)0.145 (3)0.0399 (14)0.073 (3)0.0098 (15)0.0106 (17)
O20.140 (2)0.098 (2)0.0756 (19)0.0266 (19)0.0348 (16)0.0260 (16)
O30.142 (2)0.0497 (13)0.0462 (13)0.0046 (15)0.0053 (14)0.0065 (11)
N10.0510 (13)0.0560 (14)0.0315 (12)0.0114 (12)0.0010 (9)0.0005 (10)
C10.0572 (18)0.091 (2)0.0366 (16)0.0072 (17)0.0049 (13)0.0103 (16)
C20.063 (2)0.121 (3)0.0386 (17)0.013 (2)0.0052 (14)0.0098 (19)
C30.101 (3)0.108 (3)0.0381 (18)0.053 (2)0.0003 (17)0.0101 (18)
C40.110 (3)0.066 (2)0.0409 (18)0.029 (2)0.0179 (17)0.0216 (15)
C50.084 (2)0.0530 (18)0.0411 (16)0.0164 (17)0.0158 (14)0.0134 (14)
C60.107 (3)0.0494 (19)0.062 (2)0.0023 (19)0.0224 (19)0.0194 (17)
C70.101 (3)0.064 (2)0.060 (2)0.022 (2)0.0052 (18)0.0133 (17)
C80.0536 (16)0.0511 (17)0.0458 (16)0.0029 (14)0.0109 (13)0.0032 (13)
C90.0501 (15)0.0467 (16)0.0345 (14)0.0063 (13)0.0094 (11)0.0036 (12)
C100.0513 (16)0.0522 (17)0.0341 (14)0.0082 (13)0.0094 (11)0.0108 (12)
C110.0452 (14)0.0539 (16)0.0334 (14)0.0051 (13)0.0006 (11)0.0073 (12)
C120.0443 (15)0.0511 (16)0.0360 (15)0.0011 (12)0.0040 (11)0.0030 (12)
C130.0464 (15)0.0529 (16)0.0327 (14)0.0042 (13)0.0003 (11)0.0007 (12)
C140.0561 (17)0.0524 (17)0.0424 (16)0.0087 (14)0.0063 (12)0.0011 (13)
C150.0457 (16)0.099 (3)0.056 (2)0.0103 (17)0.0044 (14)0.0094 (19)
C160.0432 (16)0.089 (2)0.0571 (19)0.0029 (16)0.0008 (13)0.0058 (18)
C170.0590 (17)0.0563 (18)0.0318 (14)0.0117 (14)0.0021 (12)0.0044 (12)
C180.0523 (16)0.0623 (18)0.0357 (15)0.0129 (14)0.0031 (12)0.0056 (13)
C190.0650 (18)0.0594 (18)0.0390 (15)0.0132 (15)0.0070 (13)0.0051 (13)
C200.074 (2)0.0506 (19)0.0458 (17)0.0174 (16)0.0009 (14)0.0041 (14)
C210.111 (3)0.118 (4)0.067 (3)0.069 (3)0.018 (2)0.016 (2)
C220.0548 (17)0.0547 (17)0.0375 (15)0.0056 (13)0.0064 (12)0.0027 (12)
C230.069 (2)0.083 (2)0.0463 (18)0.0199 (19)0.0107 (15)0.0088 (17)
C240.091 (2)0.079 (2)0.0308 (16)0.0031 (19)0.0131 (15)0.0005 (15)
C250.094 (3)0.086 (3)0.0327 (16)0.026 (2)0.0056 (15)0.0043 (16)
C260.107 (3)0.080 (2)0.0372 (17)0.038 (2)0.0121 (16)0.0059 (16)
C270.089 (3)0.154 (5)0.079 (3)0.014 (3)0.002 (2)0.047 (3)
Geometric parameters (Å, º) top
O1—C31.439 (4)C13—C181.519 (4)
O1—H10.8200C13—C171.535 (4)
O2—C61.209 (4)C13—H130.9800
O3—C201.441 (4)C14—C151.524 (4)
O3—H30.8200C14—H140.9800
N1—C181.461 (4)C15—C161.506 (4)
N1—C261.467 (4)C15—H15A0.9700
N1—C221.470 (3)C15—H15B0.9700
C1—C21.536 (4)C16—C171.526 (4)
C1—C101.537 (4)C16—H16A0.9700
C1—H1A0.9700C16—H16B0.9700
C1—H1B0.9700C17—C201.534 (4)
C2—C31.506 (6)C17—H170.9800
C2—H2A0.9700C18—H18A0.9700
C2—H2B0.9700C18—H18B0.9700
C3—C41.514 (5)C19—H19A0.9600
C3—H3A0.9800C19—H19B0.9600
C4—C51.529 (4)C19—H19C0.9600
C4—H4A0.9700C20—C211.524 (5)
C4—H4B0.9700C20—C221.530 (4)
C5—C61.523 (5)C21—H21A0.9600
C5—C101.557 (4)C21—H21B0.9600
C5—H50.9800C21—H21C0.9600
C6—C71.510 (5)C22—C231.523 (4)
C7—C81.524 (5)C22—H220.9800
C7—H7A0.9700C23—C241.520 (5)
C7—H7B0.9700C23—H23A0.9700
C8—C91.534 (4)C23—H23B0.9700
C8—C141.540 (4)C24—C251.505 (5)
C8—H80.9800C24—H24A0.9700
C9—C111.524 (4)C24—H24B0.9700
C9—C101.526 (3)C25—C271.500 (6)
C9—H90.9800C25—C261.515 (4)
C10—C191.530 (4)C25—H250.9800
C11—C121.536 (4)C26—H26A0.9700
C11—H11A0.9700C26—H26B0.9700
C11—H11B0.9700C27—H27A0.9600
C12—C131.540 (4)C27—H27B0.9600
C12—C141.551 (4)C27—H27C0.9600
C12—H120.9800
C3—O1—H1109.5C8—C14—C12104.7 (2)
C20—O3—H3109.5C15—C14—H14109.4
C18—N1—C26108.9 (2)C8—C14—H14109.4
C18—N1—C22110.5 (2)C12—C14—H14109.4
C26—N1—C22112.5 (2)C16—C15—C14113.4 (2)
C2—C1—C10112.3 (3)C16—C15—H15A108.9
C2—C1—H1A109.1C14—C15—H15A108.9
C10—C1—H1A109.1C16—C15—H15B108.9
C2—C1—H1B109.1C14—C15—H15B108.9
C10—C1—H1B109.1H15A—C15—H15B107.7
H1A—C1—H1B107.9C15—C16—C17109.7 (2)
C3—C2—C1113.0 (3)C15—C16—H16A109.7
C3—C2—H2A109.0C17—C16—H16A109.7
C1—C2—H2A109.0C15—C16—H16B109.7
C3—C2—H2B109.0C17—C16—H16B109.7
C1—C2—H2B109.0H16A—C16—H16B108.2
H2A—C2—H2B107.8C16—C17—C20113.8 (2)
O1—C3—C2106.3 (4)C16—C17—C13111.1 (2)
O1—C3—C4110.2 (3)C20—C17—C13110.5 (2)
C2—C3—C4112.2 (3)C16—C17—H17107.0
O1—C3—H3A109.4C20—C17—H17107.0
C2—C3—H3A109.4C13—C17—H17107.0
C4—C3—H3A109.4N1—C18—C13113.2 (2)
C3—C4—C5111.7 (3)N1—C18—H18A108.9
C3—C4—H4A109.3C13—C18—H18A108.9
C5—C4—H4A109.3N1—C18—H18B108.9
C3—C4—H4B109.3C13—C18—H18B108.9
C5—C4—H4B109.3H18A—C18—H18B107.7
H4A—C4—H4B107.9C10—C19—H19A109.5
C6—C5—C4114.4 (3)C10—C19—H19B109.5
C6—C5—C10113.1 (3)H19A—C19—H19B109.5
C4—C5—C10112.1 (3)C10—C19—H19C109.5
C6—C5—H5105.4H19A—C19—H19C109.5
C4—C5—H5105.4H19B—C19—H19C109.5
C10—C5—H5105.4O3—C20—C21106.7 (3)
O2—C6—C7121.7 (4)O3—C20—C22106.5 (2)
O2—C6—C5122.4 (4)C21—C20—C22112.0 (3)
C7—C6—C5115.9 (3)O3—C20—C17108.0 (2)
C6—C7—C8109.3 (3)C21—C20—C17111.4 (3)
C6—C7—H7A109.8C22—C20—C17111.8 (2)
C8—C7—H7A109.8C20—C21—H21A109.5
C6—C7—H7B109.8C20—C21—H21B109.5
C8—C7—H7B109.8H21A—C21—H21B109.5
H7A—C7—H7B108.3C20—C21—H21C109.5
C7—C8—C9110.7 (3)H21A—C21—H21C109.5
C7—C8—C14120.5 (3)H21B—C21—H21C109.5
C9—C8—C14106.2 (2)N1—C22—C23110.9 (2)
C7—C8—H8106.2N1—C22—C20107.1 (2)
C9—C8—H8106.2C23—C22—C20112.5 (2)
C14—C8—H8106.2N1—C22—H22108.8
C11—C9—C10121.5 (2)C23—C22—H22108.8
C11—C9—C8101.7 (2)C20—C22—H22108.8
C10—C9—C8112.1 (2)C24—C23—C22112.0 (3)
C11—C9—H9106.9C24—C23—H23A109.2
C10—C9—H9106.9C22—C23—H23A109.2
C8—C9—H9106.9C24—C23—H23B109.2
C9—C10—C19111.2 (2)C22—C23—H23B109.2
C9—C10—C1110.5 (2)H23A—C23—H23B107.9
C19—C10—C1109.9 (3)C25—C24—C23110.5 (2)
C9—C10—C5107.4 (2)C25—C24—H24A109.5
C19—C10—C5111.7 (2)C23—C24—H24A109.5
C1—C10—C5106.0 (2)C25—C24—H24B109.5
C9—C11—C12101.5 (2)C23—C24—H24B109.5
C9—C11—H11A111.5H24A—C24—H24B108.1
C12—C11—H11A111.5C27—C25—C24113.1 (3)
C9—C11—H11B111.5C27—C25—C26113.5 (3)
C12—C11—H11B111.5C24—C25—C26108.4 (3)
H11A—C11—H11B109.3C27—C25—H25107.1
C11—C12—C13116.2 (2)C24—C25—H25107.1
C11—C12—C14103.8 (2)C26—C25—H25107.1
C13—C12—C14117.3 (2)N1—C26—C25114.0 (3)
C11—C12—H12106.2N1—C26—H26A108.7
C13—C12—H12106.2C25—C26—H26A108.7
C14—C12—H12106.2N1—C26—H26B108.7
C18—C13—C17109.5 (2)C25—C26—H26B108.7
C18—C13—C12111.8 (2)H26A—C26—H26B107.6
C17—C13—C12114.2 (2)C25—C27—H27A109.5
C18—C13—H13107.0C25—C27—H27B109.5
C17—C13—H13107.0H27A—C27—H27B109.5
C12—C13—H13107.0C25—C27—H27C109.5
C15—C14—C8109.8 (2)H27A—C27—H27C109.5
C15—C14—C12114.2 (3)H27B—C27—H27C109.5
C10—C1—C2—C355.3 (4)C7—C8—C14—C12134.6 (3)
C1—C2—C3—O1170.6 (3)C9—C8—C14—C127.8 (3)
C1—C2—C3—C450.1 (4)C11—C12—C14—C1599.1 (3)
O1—C3—C4—C5169.3 (3)C13—C12—C14—C1530.6 (3)
C2—C3—C4—C551.1 (4)C11—C12—C14—C821.0 (3)
C3—C4—C5—C6171.9 (3)C13—C12—C14—C8150.7 (2)
C3—C4—C5—C1057.6 (4)C8—C14—C15—C16161.4 (3)
C4—C5—C6—O20.5 (5)C12—C14—C15—C1644.3 (4)
C10—C5—C6—O2129.5 (3)C14—C15—C16—C1760.4 (4)
C4—C5—C6—C7180.0 (3)C15—C16—C17—C20172.6 (3)
C10—C5—C6—C750.0 (4)C15—C16—C17—C1361.9 (3)
O2—C6—C7—C8129.2 (4)C18—C13—C17—C1677.8 (3)
C5—C6—C7—C850.3 (4)C12—C13—C17—C1648.4 (3)
C6—C7—C8—C955.0 (4)C18—C13—C17—C2049.5 (3)
C6—C7—C8—C14179.8 (3)C12—C13—C17—C20175.7 (2)
C7—C8—C9—C11166.2 (3)C26—N1—C18—C13173.5 (3)
C14—C8—C9—C1133.7 (3)C22—N1—C18—C1362.5 (3)
C7—C8—C9—C1062.6 (3)C17—C13—C18—N154.3 (3)
C14—C8—C9—C10164.9 (2)C12—C13—C18—N1178.2 (2)
C11—C9—C10—C1956.1 (3)C16—C17—C20—O3172.0 (2)
C8—C9—C10—C1964.2 (3)C13—C17—C20—O362.3 (3)
C11—C9—C10—C166.2 (3)C16—C17—C20—C2155.1 (4)
C8—C9—C10—C1173.5 (2)C13—C17—C20—C21179.1 (3)
C11—C9—C10—C5178.7 (3)C16—C17—C20—C2271.1 (3)
C8—C9—C10—C558.3 (3)C13—C17—C20—C2254.7 (3)
C2—C1—C10—C9173.8 (3)C18—N1—C22—C23174.1 (2)
C2—C1—C10—C1963.1 (3)C26—N1—C22—C2352.1 (3)
C2—C1—C10—C557.8 (4)C18—N1—C22—C2062.8 (3)
C6—C5—C10—C951.2 (3)C26—N1—C22—C20175.3 (3)
C4—C5—C10—C9177.6 (2)O3—C20—C22—N157.7 (3)
C6—C5—C10—C1971.0 (3)C21—C20—C22—N1174.0 (3)
C4—C5—C10—C1960.2 (3)C17—C20—C22—N160.1 (3)
C6—C5—C10—C1169.4 (3)O3—C20—C22—C2364.4 (3)
C4—C5—C10—C159.5 (3)C21—C20—C22—C2351.9 (4)
C10—C9—C11—C12171.7 (2)C17—C20—C22—C23177.8 (2)
C8—C9—C11—C1246.4 (3)N1—C22—C23—C2453.3 (4)
C9—C11—C12—C13172.4 (2)C20—C22—C23—C24173.2 (2)
C9—C11—C12—C1442.0 (3)C22—C23—C24—C2556.3 (4)
C11—C12—C13—C18144.6 (2)C23—C24—C25—C2771.1 (4)
C14—C12—C13—C1891.7 (3)C23—C24—C25—C2655.7 (4)
C11—C12—C13—C1790.4 (3)C18—N1—C26—C25178.3 (3)
C14—C12—C13—C1733.2 (3)C22—N1—C26—C2555.4 (4)
C7—C8—C14—C15102.4 (3)C27—C25—C26—N170.2 (4)
C9—C8—C14—C15130.7 (3)C24—C25—C26—N156.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.821.992.748 (3)154
O3—H3···N10.822.272.727 (3)116
Symmetry code: (i) x+1, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC27H43NO3
Mr429.62
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)6.6185 (5), 12.3948 (8), 14.5069 (10)
β (°) 90.822 (1)
V3)1189.95 (14)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.52 × 0.35 × 0.20
Data collection
DiffractometerSiemens SMART/CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7280, 2455, 1789
Rint0.032
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.111, 0.99
No. of reflections2455
No. of parameters285
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.18

Computer programs: SMART (Bruker, 1998a), SMART and SAINT (Bruker, 1998a), XPREP in SHELXTL (Sheldrick, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1998b), SHELXTL (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.821.992.748 (3)154
O3—H3···N10.822.272.727 (3)116
Symmetry code: (i) x+1, y+1/2, z+1.
 

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