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In the title compound, 4-(3β-hydroxy-17-oxoandrost-5-en-16-ylidenemethyl)benzonitrile, C27H31NO2, rings A and C of the steroid nucleus are in chair conformations. The central six-membered ring B is in an 8β,9α-half-chair conformation, while the five-membered ring D adopts a 13β,14α-half-chair conformation. The cyano­benzyl­idene moiety has an E configuration with respect to the carbonyl group at position C17. The dihedral angle between the planes of the steroid nucleus and the cyano­benzyl­idene moiety is 22.61 (15)°. Intermolecular O—H...N hydrogen bonds formed between the hydroxyl group of the steroid and the N atom of the cyano­benzyl­idene moiety of symmetry-related mol­ecules link the steroid mol­ecules into chains which run parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103005419/gd1244sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103005419/gd1244Isup2.hkl
Contains datablock I

CCDC reference: 211751

Comment top

The present study of the title compound, (I), is the 11t h in our series of X-ray crystal-structure analyses of androstene and its derivatives (Thamotharan et al., 2002, and references therein). The conformation of steroids having flexible unsaturated ring and/or substituents is of particular interest. We are particularly interested in studying the conformational flexibilities of the steroids resulting from various substitutions at the C3, C16 and C17 positions. The crystals of (I) are enantiomerically pure. However, due to the absence of significant anomalous scatterers in the compound, the absolute configuration of the molecule has not been determined by the X-ray diffraction experiment. The enantiomer used in the refinement was assigned to correspond to that of the known chiral centre in a precursor molecule, namely dehydroepiandrosterone (Weeks et al., 1971), which remained unchanged during the synthesis of (I).

Among the few conformational options, both methyl groups of the steroidal nucleus adopt the expected staggered arrangements. The geometry of the rings is trans at the B/C and C/D ring junctions (see Scheme and Fig. 1).

The C5—C6 distance of 1.318 (6) Å is comparable with that of the related structure (Bhacca et al., 1996) and confirms the localization of the double bond at this position. Rings A and C are slightly flattened, the mean values of their torsion angles being 52.5 (2) and 55.2 (2)°, respectively. Both ring conformations are close to that of a chair as shown by the values of Cremer & Pople (1975) puckering parameters [ring A: Q = 0.538 (5) Å, θ = 9.3 (5)°, ϕ = 81 (3)° for the atom sequence C1—C2—C3—C4—C5—C10; ring C: Q = 0.565 (5) Å, θ = 5.8 (5)°,ϕ = 266 (6)° for the atom sequence C8—C9—C11—C12—C13—C14]. Thus, the presence of the hydroxyl group bonded to C3 has not disturbed the usual chair conformation of ring A of the steroidal nucleus. The C3—O31 bond is oriented equatorially and (+)antiperiplanar to the C3—C4 bond. The dihedral angle between the planes of the cyanobenzylidene group and the steroidal nucleus is 22.61 (15)°.

Due to the C5C6 double bond, the environment of atom C5 is planar, and hence ring B adopts the 8β,9α-half-chair conformation generally found in steroids with a C5C6 double bond (Thamotharan et al., 2002, and references therein), with puckering parameters Q = 0.464 (2) Å, θ = 49.8 (6)° and ϕ =217.9 (7)° for the atom sequence C5—C6—C7—C8—C9—C10. The five-membered ring D exhibits a 13β,14α-half-chair conformation when compared to the unsubstituted dehydroxy steroid nucleus in which ring D is in a 14α-envelope conformation. It seems that a bulky sustitution of cyanobenzylidene moiety caused conformational change observed in ring D in (I) ϕm = 42.9 (3)° for the atoms sequence C13—C14—C15—C16—C17 (Altona et al., 1968).

The C17—C16—C20—C21 torsion angle of 171.1 (4)° indicates that the cyanobenzylidene moiety has an E configuration with respect to the carbonyl group at position C17 as has been observed in our previous compound (Thamotharan et al., 2002)·The C15—C16—C20 exocyclic angle of 133.0 (4)° is significantly larger than the normal value of 120° and this may be due to the steric repulsion between atoms H15B and H22 (2.41 Å). In (I), the skeletal bond angles are close to the expected values (Duax et al., 1976).

In the crystal, the steroid nucleus forms head to tail chains of O—H···N intermolecular hydrogen bonds involving the O—H group and the N atom of cyanobenzylidene moiety of a symmetry-related molecule. This interaction links the steroid molecules into chains which run parellel to the [110] direction. These hydrogen bonds form a C(18) graph-set motif (Bernstein et al., 1995).

Experimental top

A mixture of a dehydroepiandrosterone (0.5 g), sodium hydroxide (0.75 g) and 4-cyanobenzaldehyde (0.75 g) in methanol (10 ml) was stirred for 1.5 h at room temperature. The reaction mixture was added to ice cold water. The precipitate was filtered, washed thorougly with water and crystallized from methanol to afford crystals of (I); yield: 0.23 g (43%) and m.p. 565–571 K. Analysis: UVmax(MeOH): 296.2 nm (logε = 4.35); IRmax: 2980, 2210. 1720, 1640 and 900 cm−1. 1H NMR: 0.99 (s, 3H, 18-CH3), 1.08 (s, 3H, 19-CH3), 3.50 (m, 1H, 3-H), 5.40 (d, 1H, 6-CH), 3.9 (s) and 7.4 (s) [0.29:1 area ratio, 1H, vinyl-H of 16-(4-cyanobenzylidene)], 7.60 (d, 2H, Jo = 8.4, 2-CH and 6-CH aromatic proton), 7.70 (d, 2H, Jo = 8.2, 3-CH and 5-CH aromatic proton); calculated for C27H31NO2: C 80.8, H 7.8, N,3.5%; found: C 80.8, H 7.8, N 3.6%.

Refinement top

The methyl H atoms were constrained to an ideal geometry (C—H = 0.96 Å), with Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C bonds. All remaining H atoms were placed in geometrically idealized positions (C—H = 0.95–1.00 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C), except for the hydroxyl H atom, which was located in a difference Fourier map and refined using the DFIX option in SHELXL97 (Sheldrick, 1997), with H31—O31 = 0.81 (2) Å. It was included in the structure-factor calculations with Uiso(H31) = 1.2Ueq(O31). The Friedel pairs were merged before the final refinement and the absolute configuration was assigned to correspond with that of the known chiral centres in a precursor molecule which remained unchanged during the synthesis of the title compound.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Version 1.64.02; Farrugia, 1999); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2002).

Figures top
[Figure 1] Fig. 1. View of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by circles of arbitrary radii.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of a chain by O—H···N interactions. Atoms marked with a hash (#) and asterisk (*) are at the symmetry positions (1 + x, −1 + y, z) and (−1 + x, 1 + y, z), respectively.
16-(4-Cyanobenzylidene)-17-oxoandrost-5-en-3β-ol top
Crystal data top
C27H31NO2F(000) = 432
Mr = 401.53Dx = 1.220 Mg m3
Monoclinic, P21Melting point = 565–571 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 6.005 (3) ÅCell parameters from 25 reflections
b = 17.448 (4) Åθ = 20–30°
c = 10.453 (5) ŵ = 0.08 mm1
β = 93.846 (4)°T = 293 K
V = 1092.8 (8) Å3Block, pale yellow
Z = 20.25 × 0.20 × 0.15 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1520 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
non–profiled ω/2θ scansh = 07
Absorption correction: ψ scan
(North et al., 1968)
k = 020
Tmin = 0.981, Tmax = 0.989l = 1212
2184 measured reflections2 standard reflections every 60 min
1986 independent reflections intensity decay: 4%
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)] = 0.054Hydrogen site location: geom & difmap
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.082P)2]
where P = (Fo2 + 2Fc2)/3
1986 reflections(Δ/σ)max < 0.001
276 parametersΔρmax = 0.20 e Å3
2 restraintsΔρmin = 0.21 e Å3
Crystal data top
C27H31NO2V = 1092.8 (8) Å3
Mr = 401.53Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.005 (3) ŵ = 0.08 mm1
b = 17.448 (4) ÅT = 293 K
c = 10.453 (5) Å0.25 × 0.20 × 0.15 mm
β = 93.846 (4)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1520 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.033
Tmin = 0.981, Tmax = 0.9892 standard reflections every 60 min
2184 measured reflections intensity decay: 4%
1986 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0542 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.20 e Å3
1986 reflectionsΔρmin = 0.21 e Å3
276 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
C10.6176 (7)0.9445 (3)0.7316 (4)0.0427 (11)
H1A0.52350.94720.65260.051*
H1B0.52790.92410.79750.051*
C20.6909 (8)1.0249 (3)0.7695 (5)0.0469 (12)
H2A0.77091.04760.70130.056*
H2B0.56081.05630.78180.056*
C30.8401 (9)1.0232 (3)0.8918 (4)0.0472 (12)
H30.75681.00110.96040.057*
C41.0418 (8)0.9741 (3)0.8734 (5)0.0473 (12)
H4A1.13110.97070.95400.057*
H4B1.13200.99840.81140.057*
C50.9813 (7)0.8942 (2)0.8277 (4)0.0345 (10)
C61.0714 (7)0.8333 (3)0.8848 (4)0.0398 (10)
H61.17240.84200.95470.048*
C71.0280 (8)0.7515 (3)0.8486 (4)0.0400 (11)
H7A0.94540.72720.91420.048*
H7B1.16940.72490.84550.048*
C80.8955 (7)0.7432 (2)0.7183 (4)0.0330 (10)
H80.99820.74850.64980.040*
C90.7158 (7)0.8060 (2)0.7022 (4)0.0351 (10)
H90.62180.80020.77470.042*
C100.8128 (7)0.8882 (2)0.7122 (4)0.0360 (10)
C110.5602 (9)0.7932 (3)0.5797 (5)0.0507 (13)
H11A0.43860.82980.57900.061*
H11B0.64360.80320.50520.061*
C120.4629 (8)0.7125 (3)0.5688 (5)0.0501 (13)
H12A0.36150.70460.63610.060*
H12B0.37860.70690.48690.060*
C130.6458 (7)0.6528 (3)0.5802 (4)0.0367 (10)
C140.7854 (7)0.6651 (3)0.7075 (4)0.0353 (9)
H140.67840.66400.77430.042*
C150.9239 (8)0.5911 (3)0.7263 (4)0.0392 (10)
H15A1.05810.59330.67970.047*
H15B0.96490.58190.81630.047*
C160.7642 (7)0.5302 (3)0.6715 (4)0.0368 (10)
C170.5756 (8)0.5710 (3)0.5976 (4)0.0397 (11)
C180.7890 (9)0.6528 (3)0.4628 (4)0.0525 (13)
H18A0.69770.63880.38750.079*
H18B0.90840.61640.47630.079*
H18C0.85000.70300.45170.079*
C190.9302 (8)0.9100 (3)0.5920 (4)0.0465 (12)
H19A1.02710.86910.56980.070*
H19B1.01640.95580.60830.070*
H19C0.82070.91900.52240.070*
C200.7660 (8)0.4545 (3)0.6765 (4)0.0434 (11)
H200.64160.43120.63540.052*
C210.9304 (7)0.4011 (3)0.7358 (4)0.0394 (11)
C221.1426 (8)0.4235 (3)0.7832 (5)0.0493 (12)
H221.18490.47470.77780.059*
C231.2905 (8)0.3708 (3)0.8380 (5)0.0496 (12)
H231.42980.38690.87190.060*
C241.2336 (8)0.2939 (3)0.8431 (4)0.0449 (11)
C251.0228 (9)0.2704 (3)0.7919 (4)0.0499 (13)
H250.98240.21900.79390.060*
C260.8769 (9)0.3237 (3)0.7392 (4)0.0456 (12)
H260.73800.30770.70450.055*
C271.3894 (9)0.2387 (3)0.8989 (5)0.0571 (13)
O170.3977 (6)0.5425 (2)0.5616 (3)0.0577 (9)
O310.9180 (6)1.0977 (2)0.9305 (4)0.0648 (11)
H310.802 (6)1.121 (3)0.929 (5)0.077*
N281.5144 (9)0.1959 (3)0.9447 (5)0.0798 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.032 (3)0.042 (3)0.053 (3)0.011 (2)0.003 (2)0.001 (2)
C20.044 (3)0.036 (3)0.060 (3)0.009 (2)0.002 (2)0.001 (2)
C30.056 (3)0.037 (3)0.049 (3)0.005 (2)0.002 (2)0.001 (2)
C40.038 (3)0.043 (3)0.060 (3)0.002 (2)0.007 (2)0.002 (2)
C50.032 (2)0.031 (2)0.040 (2)0.0017 (18)0.0019 (18)0.0002 (18)
C60.033 (2)0.039 (3)0.047 (2)0.000 (2)0.0077 (19)0.001 (2)
C70.037 (3)0.039 (3)0.043 (2)0.003 (2)0.0057 (19)0.002 (2)
C80.034 (3)0.028 (2)0.037 (2)0.0058 (19)0.0002 (17)0.0018 (17)
C90.029 (2)0.033 (2)0.042 (2)0.0037 (19)0.0010 (18)0.0014 (18)
C100.035 (2)0.031 (2)0.042 (2)0.0045 (19)0.0009 (18)0.0034 (18)
C110.045 (3)0.040 (3)0.064 (3)0.010 (2)0.014 (2)0.000 (2)
C120.040 (3)0.043 (3)0.065 (3)0.005 (2)0.016 (2)0.005 (2)
C130.037 (2)0.033 (3)0.039 (2)0.001 (2)0.0048 (18)0.0008 (18)
C140.035 (2)0.033 (2)0.038 (2)0.003 (2)0.0003 (18)0.0018 (18)
C150.041 (3)0.031 (2)0.046 (2)0.002 (2)0.0028 (19)0.0013 (19)
C160.036 (3)0.036 (3)0.039 (2)0.001 (2)0.0053 (19)0.0030 (18)
C170.041 (3)0.036 (3)0.042 (2)0.001 (2)0.000 (2)0.0025 (19)
C180.057 (3)0.052 (3)0.048 (3)0.004 (3)0.002 (2)0.000 (2)
C190.052 (3)0.041 (3)0.046 (3)0.002 (2)0.004 (2)0.004 (2)
C200.042 (3)0.041 (3)0.046 (3)0.005 (2)0.003 (2)0.005 (2)
C210.042 (3)0.036 (3)0.041 (2)0.003 (2)0.008 (2)0.0016 (19)
C220.050 (3)0.032 (3)0.066 (3)0.002 (2)0.004 (2)0.002 (2)
C230.042 (3)0.044 (3)0.062 (3)0.000 (2)0.002 (2)0.002 (2)
C240.050 (3)0.037 (3)0.048 (3)0.011 (2)0.009 (2)0.004 (2)
C250.063 (4)0.034 (3)0.053 (3)0.002 (2)0.007 (2)0.000 (2)
C260.052 (3)0.035 (3)0.049 (3)0.000 (2)0.001 (2)0.004 (2)
C270.056 (4)0.050 (3)0.066 (3)0.003 (3)0.010 (3)0.001 (3)
O170.046 (2)0.050 (2)0.074 (2)0.0096 (18)0.0136 (17)0.0042 (18)
O310.066 (3)0.035 (2)0.090 (3)0.0081 (18)0.018 (2)0.0153 (19)
N280.071 (3)0.055 (3)0.111 (4)0.018 (3)0.017 (3)0.001 (3)
Geometric parameters (Å, º) top
C1—C21.515 (6)C13—C171.501 (7)
C1—C101.553 (6)C13—C141.540 (5)
C1—H1A0.9700C13—C181.545 (6)
C1—H1B0.9700C14—C151.540 (6)
C2—C31.512 (7)C14—H140.9800
C2—H2A0.9700C15—C161.518 (6)
C2—H2B0.9700C15—H15A0.9700
C3—O311.430 (6)C15—H15B0.9700
C3—C41.507 (7)C16—C201.322 (6)
C3—H30.9800C16—C171.506 (6)
C4—C51.509 (6)C17—O171.216 (5)
C4—H4A0.9700C18—H18A0.9600
C4—H4B0.9700C18—H18B0.9600
C5—C61.318 (6)C18—H18C0.9600
C5—C101.526 (6)C19—H19A0.9600
C6—C71.495 (6)C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C7—C81.538 (6)C20—C211.465 (6)
C7—H7A0.9700C20—H200.9300
C7—H7B0.9700C21—C261.388 (7)
C8—C141.516 (6)C21—C221.392 (7)
C8—C91.540 (5)C22—C231.377 (7)
C8—H80.9800C22—H220.9300
C9—C101.549 (6)C23—C241.385 (7)
C9—C111.550 (6)C23—H230.9300
C9—H90.9800C24—C251.403 (7)
C10—C191.530 (6)C24—C271.439 (7)
C11—C121.525 (7)C25—C261.369 (7)
C11—H11A0.9700C25—H250.9300
C11—H11B0.9700C26—H260.9300
C12—C131.513 (6)C27—N281.141 (7)
C12—H12A0.9700O31—H310.81 (2)
C12—H12B0.9700
C2—C1—C10114.3 (4)C13—C12—H12B109.5
C2—C1—H1A108.7C11—C12—H12B109.5
C10—C1—H1A108.7H12A—C12—H12B108.0
C2—C1—H1B108.7C17—C13—C12117.1 (4)
C10—C1—H1B108.7C17—C13—C1499.7 (3)
H1A—C1—H1B107.6C12—C13—C14108.8 (4)
C3—C2—C1110.4 (4)C17—C13—C18105.8 (4)
C3—C2—H2A109.6C12—C13—C18112.2 (4)
C1—C2—H2A109.6C14—C13—C18112.8 (4)
C3—C2—H2B109.6C8—C14—C13113.5 (3)
C1—C2—H2B109.6C8—C14—C15121.0 (3)
H2A—C2—H2B108.1C13—C14—C15104.6 (3)
O31—C3—C4107.6 (4)C8—C14—H14105.5
O31—C3—C2112.7 (4)C13—C14—H14105.5
C4—C3—C2109.8 (4)C15—C14—H14105.5
O31—C3—H3108.9C16—C15—C14102.5 (4)
C4—C3—H3108.9C16—C15—H15A111.3
C2—C3—H3108.9C14—C15—H15A111.3
C3—C4—C5112.8 (4)C16—C15—H15B111.3
C3—C4—H4A109.0C14—C15—H15B111.3
C5—C4—H4A109.0H15A—C15—H15B109.2
C3—C4—H4B109.0C20—C16—C17119.8 (4)
C5—C4—H4B109.0C20—C16—C15133.0 (4)
H4A—C4—H4B107.8C17—C16—C15107.3 (4)
C6—C5—C4121.3 (4)O17—C17—C13126.9 (4)
C6—C5—C10122.2 (4)O17—C17—C16125.4 (4)
C4—C5—C10116.5 (4)C13—C17—C16107.7 (4)
C5—C6—C7126.6 (4)C13—C18—H18A109.5
C5—C6—H6116.7C13—C18—H18B109.5
C7—C6—H6116.7H18A—C18—H18B109.5
C6—C7—C8112.7 (4)C13—C18—H18C109.5
C6—C7—H7A109.1H18A—C18—H18C109.5
C8—C7—H7A109.1H18B—C18—H18C109.5
C6—C7—H7B109.1C10—C19—H19A109.5
C8—C7—H7B109.1C10—C19—H19B109.5
H7A—C7—H7B107.8H19A—C19—H19B109.5
C14—C8—C7110.3 (3)C10—C19—H19C109.5
C14—C8—C9109.5 (3)H19A—C19—H19C109.5
C7—C8—C9110.3 (3)H19B—C19—H19C109.5
C14—C8—H8108.9C16—C20—C21131.0 (4)
C7—C8—H8108.9C16—C20—H20114.5
C9—C8—H8108.9C21—C20—H20114.5
C8—C9—C10113.2 (3)C26—C21—C22118.2 (4)
C8—C9—C11111.5 (3)C26—C21—C20118.6 (4)
C10—C9—C11113.1 (3)C22—C21—C20123.1 (4)
C8—C9—H9106.1C23—C22—C21120.6 (5)
C10—C9—H9106.1C23—C22—H22119.7
C11—C9—H9106.1C21—C22—H22119.7
C5—C10—C19108.4 (4)C22—C23—C24120.6 (5)
C5—C10—C9110.1 (3)C22—C23—H23119.7
C19—C10—C9111.5 (3)C24—C23—H23119.7
C5—C10—C1108.6 (3)C23—C24—C25119.2 (4)
C19—C10—C1110.1 (4)C23—C24—C27120.6 (5)
C9—C10—C1108.1 (3)C25—C24—C27120.3 (5)
C12—C11—C9113.7 (4)C26—C25—C24119.4 (5)
C12—C11—H11A108.8C26—C25—H25120.3
C9—C11—H11A108.8C24—C25—H25120.3
C12—C11—H11B108.8C25—C26—C21121.9 (5)
C9—C11—H11B108.8C25—C26—H26119.0
H11A—C11—H11B107.7C21—C26—H26119.0
C13—C12—C11110.9 (4)N28—C27—C24178.7 (6)
C13—C12—H12A109.5C3—O31—H31101 (5)
C11—C12—H12A109.5
C10—C1—C2—C357.9 (5)C7—C8—C14—C1555.5 (5)
C1—C2—C3—O31178.8 (4)C9—C8—C14—C15177.0 (4)
C1—C2—C3—C458.8 (5)C17—C13—C14—C8176.7 (4)
O31—C3—C4—C5178.0 (4)C12—C13—C14—C860.2 (5)
C2—C3—C4—C555.0 (5)C18—C13—C14—C864.9 (5)
C3—C4—C5—C6130.3 (5)C17—C13—C14—C1542.8 (4)
C3—C4—C5—C1050.1 (6)C12—C13—C14—C15165.9 (4)
C4—C5—C6—C7179.4 (4)C18—C13—C14—C1568.9 (5)
C10—C5—C6—C70.1 (7)C8—C14—C15—C16164.8 (3)
C5—C6—C7—C811.0 (7)C13—C14—C15—C1635.2 (4)
C6—C7—C8—C14159.7 (4)C14—C15—C16—C20167.4 (5)
C6—C7—C8—C938.6 (5)C14—C15—C16—C1713.5 (4)
C14—C8—C9—C10179.8 (3)C12—C13—C17—O1727.2 (6)
C7—C8—C9—C1058.2 (4)C14—C13—C17—O17144.2 (5)
C14—C8—C9—C1151.3 (4)C18—C13—C17—O1798.6 (5)
C7—C8—C9—C11172.8 (4)C12—C13—C17—C16151.4 (4)
C6—C5—C10—C19104.9 (5)C14—C13—C17—C1634.3 (4)
C4—C5—C10—C1974.6 (5)C18—C13—C17—C1682.8 (4)
C6—C5—C10—C917.3 (6)C20—C16—C17—O1715.7 (7)
C4—C5—C10—C9163.1 (4)C15—C16—C17—O17165.1 (4)
C6—C5—C10—C1135.5 (4)C20—C16—C17—C13165.7 (4)
C4—C5—C10—C145.0 (5)C15—C16—C17—C1313.5 (5)
C8—C9—C10—C546.4 (4)C17—C16—C20—C21177.1 (4)
C11—C9—C10—C5174.5 (4)C15—C16—C20—C211.8 (9)
C8—C9—C10—C1974.0 (4)C16—C20—C21—C26172.6 (5)
C11—C9—C10—C1954.1 (5)C16—C20—C21—C2210.9 (8)
C8—C9—C10—C1164.9 (3)C26—C21—C22—C233.4 (7)
C11—C9—C10—C167.0 (4)C20—C21—C22—C23180.0 (4)
C2—C1—C10—C549.0 (5)C21—C22—C23—C242.2 (7)
C2—C1—C10—C1969.6 (5)C22—C23—C24—C250.1 (7)
C2—C1—C10—C9168.4 (4)C22—C23—C24—C27179.2 (5)
C8—C9—C11—C1251.2 (5)C23—C24—C25—C260.6 (7)
C10—C9—C11—C12179.8 (4)C27—C24—C25—C26179.9 (4)
C9—C11—C12—C1354.0 (6)C24—C25—C26—C210.7 (7)
C11—C12—C13—C17168.2 (4)C22—C21—C26—C252.7 (7)
C11—C12—C13—C1456.2 (5)C20—C21—C26—C25179.4 (4)
C11—C12—C13—C1869.2 (5)C19—C10—C13—C1810.0 (4)
C7—C8—C14—C13179.0 (4)H31—O31—C3—C4173 (4)
C9—C8—C14—C1357.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O31—H31···N28i0.81 (2)2.18 (2)2.980 (7)172 (6)
Symmetry code: (i) x1, y+1, z.

Experimental details

Crystal data
Chemical formulaC27H31NO2
Mr401.53
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)6.005 (3), 17.448 (4), 10.453 (5)
β (°) 93.846 (4)
V3)1092.8 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.981, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
2184, 1986, 1520
Rint0.033
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.136, 1.05
No. of reflections1986
No. of parameters276
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.21

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), WinGX (Version 1.64.02; Farrugia, 1999), SHELXL97 and PLATON (Spek, 2002).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O31—H31···N28i0.81 (2)2.18 (2)2.980 (7)172 (6)
Symmetry code: (i) x1, y+1, z.
 

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