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In this paper, we report on the X-ray analysis of 5-butyl­thevinone (7α-acetyl-4,5α-epoxy-3,6-di­methoxy-5β-butyl-17-methyl-6α,14α-ethenoisomorphinan), C27H35NO4. This compound is the sole product of a Diels–Alder reaction of 5-butyl­thebaine with 3-buten-2-one, through attack of the dienophile on the β-face of the diene, even though it has been suggested that the introduction of 5β-substituents tends to hinder attack from the β-face, and leads to the production of exo-etheno adducts through attack from the α-face.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802023413/ac6027sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802023413/ac60273sup2.hkl
Contains datablock 3

CCDC reference: 204670

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.056
  • wR factor = 0.124
  • Data-to-parameter ratio = 12.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.42 From the CIF: _reflns_number_total 3701 Count of symmetry unique reflns 3137 Completeness (_total/calc) 117.98% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 564 Fraction of Friedel pairs measured 0.180 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.

Comment top

The orvinols are an important class of opioids which are of continued interest due to their high potency as analgesics (Casy & Parfitt, 1986; Maat et al., 1999; Coop et al., 2000; Derrick et al., 2000; Meada & Coop, 2001). The preparation of the orvinols involves a Diels–Alder addition of a dienophile to the diene system of thebaine, (1), which occurs from the least hindered β-face (endo-adducts). Several reports have shown that the introduction of small substituents into the 5-position of thebaine (Boden et al., 1982) hinders the β-face to attack, giving rise to a small quantity of the adduct arising from attack from the α-face (exo-adducts) (Woudenberg et al., 1992, 1994; Baas et al., 1997; Maat et al., 1999). In an attempt to brominate the 5-position of thebaine, we inadvertently obtained the 5β-butylated derivative, (2), and considered that this compound would possess greater steric hindrance than the small substituents already investigated. We hypothesized that a greater quantity of the exo-adduct would result.

As expected a slow reaction was observed, but unexpectedly the only product formed was the endo-adduct, (3), resulting from attack from the β-face. Thus, the introduction of a large β-butyl group does not favor attack from the α-face.

The title compound, (3), crystallized in the monoclinic space group P21 with one molecule in the asymmetric unit (Fig. 1). The absolute configuration could not be determined from the X-ray data and was therefore set based on heroin (Deschamps et al., 1996).

Experimental top

Synthesis of 5-butylthebaine, (2): to a stirred solution of TMEDA (0.78 ml, 5.1 mmol) in dry tetrahydrofuran (THF, 10 ml), cooled to 195 K, was added a solution of BuLi solution (12 ml of a 1.11 M solution in hexane, 13.3 mmol). The mixture was stirred for 30 min before the slow addition of a solution of thebaine, (1) (0.93 g, 3.0 mmol) in dry THF (20 ml). The solution was allowed to stir at 195 K for 1 h, followed by the addition of N-bromosuccinimide (0.60 g, 3.4 mmol) in THF (10 ml). After stirring for a further 30 min at 195 K, the solution was allowed to come to room temperature over 2 h, and stirred at room temperature overnight. After removal of the solvent, the residue was taken up in CHCl3 (50 ml), washed with NaHCO3 solution, water, and brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel (gradient from 2% to 10% MeOH in CH2Cl2) to afford (2) (0.61 g, 55%) as a colorless foam as the sole product. 1H NMR (300 MHz, CDCl3): δ 0.90 (t, 3H, J = 6.6 Hz, CH3 in butyl group), 2.46 (s, NCH3), 3.29 (d, 1H, J = 18.3 Hz), 3.56 (s, 3H, OMe), 3.65 (d, 1H, J = 6.1 Hz), 3.83 (s, 3H, OMe), 5.07 (d, 1H, J = 6.4 Hz), 5.55 (d, 1H, J = 6.4 Hz), 6.57 (d, 1H, J = 8.3 Hz), 6.63 (d, 1H, J = 8.3 Hz).

Synthesis of 5-butylthevinone, (3): a mixture of (2) (0.56 g, 1.52 mmol), 3-buten-2-one (4.8 ml, 57.7 mmol) and toluene (10 ml) was heated under reflux for 13 d. The reaction mixture was concentrated, and the residue was purified by flash chromatography on silica gel (gradient: 1% to 3% MeOH in CH2Cl2) to afford (3) (0.28 g, 42%) as a colorless solid as the only product. Evaporative recrystallization from MeOH provided crystals suitable for X-ray analysis; m.p. 456–457 K. 1H NMR (300 MHz, CDCl3): δ 0.93 (t, 3H, J = 6.6 Hz, CH3 in butyl group), 2.14 (s, 3H, Me in acetyl), 2.34 (s, 3H, NMe), 3.11 (d, 1H, J = 6.4 Hz), 3.24 (d, 1H, J = 18.3 Hz), 3.58 (s, 3H, OMe), 3.82 (s, 3H, OMe), 5.48 (d, 1H, J = 8.8 Hz), 5.97 (d, 1H, J = 8.8 Hz), 6.47 (d, 1H, J = 8.0 Hz), 6.61 (d, 1H, J = 8.0 Hz). 13C NMR (75 MHz, CDCl3): δ 210.10, 148.64, 141.65, 135.99, 129.29, 125.32, 119.14, 115.09, 100.34, 84.04, 60.88, 57.74, 54.86, 50.53, 49.69, 45.97, 44.83, 43.73, 32.25, 29.24 (2 C), 29.11, 28.92, 27.66, 24.16, 23.13, 14.49. EIMS m/z: 437 (M+, 47%), 394 (32%), 206 (100%).

Refinement top

The β-butyl side chain off C5 can also be modeled with a disorder of atoms C5B, C5C and C5D. Including this disorder also requires distance constraints on the C5C—C5D bond in the major component and the C5B'—C5C' and C5C'—C5D' distances in the minor component, and the anisotropic displacement parameters for C5B', C5C' and C5D'. The minor component had an occupancy of 30% or less and peaks in the final difference map were still in the area of this disordered side chain indicating the disorder may be even more complex (i.e. over more than the two positions modeled). Due to problems with modeling of the disorder this was omitted from the final refinement.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000) and XPREP (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of 5-butylthevinone, (3). Displacement ellipsoids are shown at the 20% probability level and H atoms have been omitted for clarity. The minor component of the disordered β-butyl side chain has been omitted for clarity.
(7α-acetyl-4,5α-epoxy-3,6-dimethoxy-5β-butyl-17-methyl-6α, 14α ethenoisomorphinan) top
Crystal data top
C27H35NO4F(000) = 472
Mr = 437.56Dx = 1.251 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.706 (5) ÅCell parameters from 1983 reflections
b = 7.292 (3) Åθ = 2.5–23.7°
c = 16.958 (8) ŵ = 0.08 mm1
β = 104.519 (6)°T = 298 K
V = 1161.8 (9) Å3Prism, colorless
Z = 20.64 × 0.18 × 0.06 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
3701 independent reflections
Radiation source: sealed tube2014 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ϕ and ω scansθmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan
(Bruker, 2000)
h = 1212
Tmin = 0.921, Tmax = 0.994k = 39
5557 measured reflectionsl = 2022
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0467P)2]
where P = (Fo2 + 2Fc2)/3
3701 reflections(Δ/σ)max < 0.001
290 parametersΔρmax = 0.29 e Å3
2 restraintsΔρmin = 0.25 e Å3
Crystal data top
C27H35NO4V = 1161.8 (9) Å3
Mr = 437.56Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.706 (5) ŵ = 0.08 mm1
b = 7.292 (3) ÅT = 298 K
c = 16.958 (8) Å0.64 × 0.18 × 0.06 mm
β = 104.519 (6)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
3701 independent reflections
Absorption correction: multi-scan
(Bruker, 2000)
2014 reflections with I > 2σ(I)
Tmin = 0.921, Tmax = 0.994Rint = 0.056
5557 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0562 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 0.97Δρmax = 0.29 e Å3
3701 reflectionsΔρmin = 0.25 e Å3
290 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
C10.1834 (4)0.8561 (6)0.1632 (2)0.0501 (11)
H1A0.27690.87310.16620.060*
C20.1304 (4)0.9586 (5)0.1077 (2)0.0507 (12)
H2A0.19161.03600.07150.061*
C30.0102 (4)0.9479 (5)0.1053 (2)0.0448 (10)
O30.0594 (3)1.0706 (4)0.05736 (15)0.0603 (8)
C3A0.1397 (4)0.9919 (6)0.0052 (2)0.0650 (14)
H3AA0.17051.08750.02540.097*
H3AB0.08110.90670.03160.097*
H3AC0.22130.92910.03770.097*
C40.0952 (4)0.8220 (5)0.15682 (19)0.0389 (9)
O50.2407 (2)0.8124 (3)0.17438 (13)0.0418 (7)
C50.2887 (4)0.6691 (5)0.2377 (2)0.0388 (10)
C5A0.3854 (4)0.5432 (6)0.20240 (19)0.0497 (11)
H5AA0.48030.59580.21590.060*
H5AB0.39140.42590.23000.060*
C5B0.3436 (5)0.5085 (7)0.1131 (2)0.0768 (15)
H5BA0.35590.62160.08560.092*
H5BB0.24300.47880.09780.092*
C5C0.4219 (6)0.3599 (11)0.0818 (3)0.141 (3)
H5CA0.39720.24330.10220.169*
H5CB0.38890.35700.02290.169*
C5D0.5773 (6)0.3772 (14)0.1037 (4)0.179 (4)
H5DA0.61860.26850.08730.268*
H5DB0.61090.39270.16150.268*
H5DC0.60420.48180.07650.268*
C60.3720 (4)0.7631 (5)0.3188 (2)0.0381 (10)
O60.5064 (3)0.8377 (4)0.31458 (15)0.0506 (7)
C6A0.5060 (5)1.0042 (7)0.2724 (3)0.0788 (15)
H6AA0.60181.03710.27270.118*
H6AB0.46481.09880.29860.118*
H6AC0.45090.99010.21720.118*
C70.4064 (4)0.6017 (5)0.38347 (18)0.0386 (10)
H7A0.44530.49900.35860.046*
C7A0.5211 (4)0.6634 (5)0.4592 (2)0.0416 (10)
O70.4881 (3)0.7283 (4)0.51700 (16)0.0590 (8)
C7B0.6712 (4)0.6286 (6)0.4587 (2)0.0549 (12)
H7BA0.73280.67300.50840.082*
H7BB0.69240.69090.41330.082*
H7BC0.68560.49920.45390.082*
C80.2695 (3)0.5362 (6)0.4037 (2)0.0432 (10)
H8A0.27020.57100.45900.052*
H8B0.26330.40360.39980.052*
C90.0051 (4)0.5484 (6)0.3501 (2)0.0433 (10)
H9A0.01330.57330.40550.052*
C100.1331 (4)0.6490 (5)0.2890 (2)0.0481 (11)
H10A0.21050.56210.27170.058*
H10B0.16670.74690.31810.058*
C110.0981 (4)0.7295 (5)0.2140 (2)0.0413 (10)
C120.0356 (4)0.7049 (5)0.20308 (19)0.0371 (10)
C130.1514 (4)0.5857 (5)0.25500 (18)0.0361 (9)
C140.1394 (4)0.6238 (5)0.34323 (19)0.0371 (9)
C150.1294 (4)0.3795 (5)0.2355 (2)0.0497 (11)
H15A0.12110.36110.17790.060*
H15B0.21290.31310.26530.060*
C160.0018 (4)0.2991 (6)0.2569 (2)0.0543 (12)
H16A0.08700.34460.21900.065*
H16B0.00070.16660.25200.065*
N170.0050 (3)0.3488 (5)0.33974 (18)0.0479 (9)
C170.1207 (5)0.2576 (6)0.3647 (3)0.0739 (14)
H17A0.11590.12800.35590.111*
H17B0.21020.30410.33320.111*
H17C0.11230.28070.42140.111*
C180.1592 (4)0.8259 (5)0.35837 (19)0.0430 (10)
H18A0.09180.89690.37480.052*
C190.2770 (4)0.8971 (5)0.34719 (19)0.0385 (10)
H19A0.29991.02050.35610.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.033 (2)0.057 (3)0.052 (2)0.010 (2)0.0042 (19)0.013 (2)
C20.055 (3)0.048 (3)0.041 (2)0.015 (2)0.001 (2)0.005 (2)
C30.057 (3)0.038 (3)0.036 (2)0.004 (2)0.0044 (19)0.0036 (19)
O30.080 (2)0.0472 (19)0.0531 (16)0.0137 (17)0.0152 (15)0.0109 (15)
C3A0.084 (3)0.061 (3)0.050 (2)0.003 (3)0.018 (2)0.009 (2)
C40.045 (2)0.039 (2)0.0292 (18)0.006 (2)0.0020 (16)0.0055 (18)
O50.0386 (15)0.0469 (18)0.0380 (13)0.0068 (13)0.0059 (11)0.0080 (12)
C50.041 (2)0.041 (3)0.033 (2)0.0052 (19)0.0077 (17)0.0040 (18)
C5A0.049 (2)0.057 (3)0.041 (2)0.011 (2)0.0076 (18)0.001 (2)
C5B0.099 (4)0.079 (4)0.056 (3)0.017 (3)0.026 (3)0.003 (3)
C5C0.153 (6)0.178 (7)0.078 (4)0.055 (6)0.004 (4)0.033 (4)
C5D0.101 (5)0.280 (12)0.158 (6)0.012 (7)0.037 (5)0.064 (8)
C60.034 (2)0.039 (3)0.040 (2)0.0006 (19)0.0060 (17)0.0047 (18)
O60.0414 (15)0.0484 (18)0.0605 (16)0.0028 (14)0.0100 (12)0.0131 (15)
C6A0.072 (3)0.070 (4)0.099 (3)0.012 (3)0.030 (3)0.031 (3)
C70.042 (2)0.036 (2)0.0330 (19)0.0030 (19)0.0011 (16)0.0001 (17)
C7A0.045 (2)0.036 (3)0.039 (2)0.0013 (19)0.0016 (18)0.0006 (18)
O70.0581 (17)0.069 (2)0.0460 (17)0.0038 (17)0.0053 (14)0.0138 (16)
C7B0.041 (2)0.073 (3)0.048 (2)0.008 (2)0.0076 (18)0.000 (2)
C80.046 (2)0.044 (3)0.036 (2)0.001 (2)0.0043 (17)0.0038 (19)
C90.040 (2)0.047 (3)0.042 (2)0.006 (2)0.0082 (17)0.002 (2)
C100.040 (2)0.050 (3)0.053 (2)0.001 (2)0.0102 (18)0.007 (2)
C110.038 (2)0.042 (3)0.040 (2)0.001 (2)0.0017 (18)0.0087 (19)
C120.039 (2)0.039 (3)0.0299 (19)0.003 (2)0.0021 (17)0.0057 (17)
C130.039 (2)0.035 (2)0.0328 (19)0.0021 (18)0.0059 (16)0.0002 (17)
C140.037 (2)0.035 (3)0.036 (2)0.0017 (18)0.0035 (16)0.0031 (17)
C150.053 (2)0.047 (3)0.046 (2)0.008 (2)0.008 (2)0.006 (2)
C160.054 (3)0.038 (3)0.067 (3)0.002 (2)0.007 (2)0.008 (2)
N170.046 (2)0.042 (2)0.058 (2)0.0088 (17)0.0164 (16)0.0017 (17)
C170.071 (3)0.051 (3)0.102 (4)0.009 (3)0.025 (3)0.004 (3)
C180.053 (2)0.041 (3)0.0324 (19)0.007 (2)0.0069 (18)0.0019 (18)
C190.045 (2)0.028 (2)0.040 (2)0.004 (2)0.0067 (18)0.0049 (17)
Geometric parameters (Å, º) top
C1—C111.386 (5)C7—C7A1.541 (5)
C1—C21.397 (5)C7—C81.530 (4)
C1—H1A0.9300C7—H7A0.9800
C2—C31.378 (5)C7A—O71.201 (4)
C2—H2A0.9300C7A—C7B1.481 (5)
C3—O31.373 (4)C7B—H7BA0.9600
C3—C41.387 (5)C7B—H7BB0.9600
O3—C3A1.437 (4)C7B—H7BC0.9600
C3A—H3AA0.9600C8—C141.551 (5)
C3A—H3AB0.9600C8—H8A0.9700
C3A—H3AC0.9600C8—H8B0.9700
C4—O51.370 (4)C9—N171.466 (5)
C4—C121.381 (5)C9—C141.537 (5)
O5—C51.487 (4)C9—C101.584 (5)
C5—C5A1.537 (5)C9—H9A0.9800
C5—C131.559 (5)C10—C111.516 (5)
C5—C61.569 (5)C10—H10A0.9700
C5A—C5B1.488 (5)C10—H10B0.9700
C5A—H5AA0.9700C11—C121.367 (5)
C5A—H5AB0.9700C12—C131.516 (5)
C5B—C5C1.495 (7)C13—C151.543 (6)
C5B—H5BA0.9700C13—C141.555 (4)
C5B—H5BB0.9700C14—C181.501 (5)
C5C—C5D1.466 (4)C15—C161.527 (5)
C5C—H5CA0.9700C15—H15A0.9700
C5C—H5CB0.9700C15—H15B0.9700
C5D—H5DA0.9600C16—N171.458 (5)
C5D—H5DB0.9600C16—H16A0.9700
C5D—H5DC0.9600C16—H16B0.9700
C6—O61.432 (4)N17—C171.456 (5)
C6—C191.502 (5)C17—H17A0.9600
C6—C71.586 (5)C17—H17B0.9600
O6—C6A1.408 (5)C17—H17C0.9600
C6A—H6AA0.9600C18—C191.312 (5)
C6A—H6AB0.9600C18—H18A0.9300
C6A—H6AC0.9600C19—H19A0.9300
C11—C1—C2120.8 (3)C7B—C7A—C7116.7 (3)
C11—C1—H1A119.6C7A—C7B—H7BA109.5
C2—C1—H1A119.6C7A—C7B—H7BB109.5
C3—C2—C1121.6 (4)H7BA—C7B—H7BB109.5
C3—C2—H2A119.2C7A—C7B—H7BC109.5
C1—C2—H2A119.2H7BA—C7B—H7BC109.5
O3—C3—C2118.3 (3)H7BB—C7B—H7BC109.5
O3—C3—C4124.4 (4)C7—C8—C14109.4 (3)
C2—C3—C4117.1 (4)C7—C8—H8A109.8
C3—O3—C3A115.3 (3)C14—C8—H8A109.8
O3—C3A—H3AA109.5C7—C8—H8B109.8
O3—C3A—H3AB109.5C14—C8—H8B109.8
H3AA—C3A—H3AB109.5H8A—C8—H8B108.2
O3—C3A—H3AC109.5N17—C9—C14108.5 (3)
H3AA—C3A—H3AC109.5N17—C9—C10113.9 (3)
H3AB—C3A—H3AC109.5C14—C9—C10111.4 (3)
O5—C4—C12113.6 (3)N17—C9—H9A107.6
O5—C4—C3126.0 (4)C14—C9—H9A107.6
C12—C4—C3120.0 (3)C10—C9—H9A107.6
C4—O5—C5108.2 (3)C11—C10—C9115.1 (3)
O5—C5—C5A104.5 (3)C11—C10—H10A108.5
O5—C5—C13106.4 (3)C9—C10—H10A108.5
C5A—C5—C13118.4 (3)C11—C10—H10B108.5
O5—C5—C6109.0 (3)C9—C10—H10B108.5
C5A—C5—C6111.8 (3)H10A—C10—H10B107.5
C13—C5—C6106.4 (3)C12—C11—C1116.3 (4)
C5B—C5A—C5117.4 (3)C12—C11—C10118.8 (3)
C5B—C5A—H5AA107.9C1—C11—C10123.7 (3)
C5—C5A—H5AA107.9C11—C12—C4122.8 (4)
C5B—C5A—H5AB107.9C11—C12—C13126.0 (3)
C5—C5A—H5AB107.9C4—C12—C13109.2 (3)
H5AA—C5A—H5AB107.2C12—C13—C15113.1 (3)
C5A—C5B—C5C116.9 (4)C12—C13—C14103.5 (3)
C5A—C5B—H5BA108.1C15—C13—C14109.9 (3)
C5C—C5B—H5BA108.1C12—C13—C5102.2 (3)
C5A—C5B—H5BB108.1C15—C13—C5114.7 (3)
C5C—C5B—H5BB108.1C14—C13—C5112.7 (3)
H5BA—C5B—H5BB107.3C18—C14—C9114.8 (3)
C5D—C5C—C5B115.5 (6)C18—C14—C8104.1 (3)
C5D—C5C—H5CA108.4C9—C14—C8114.2 (3)
C5B—C5C—H5CA108.4C18—C14—C13107.6 (3)
C5D—C5C—H5CB108.4C9—C14—C13107.4 (3)
C5B—C5C—H5CB108.4C8—C14—C13108.5 (3)
H5CA—C5C—H5CB107.5C16—C15—C13113.7 (3)
C5C—C5D—H5DA109.5C16—C15—H15A108.8
C5C—C5D—H5DB109.5C13—C15—H15A108.8
H5DA—C5D—H5DB109.5C16—C15—H15B108.8
C5C—C5D—H5DC109.5C13—C15—H15B108.8
H5DA—C5D—H5DC109.5H15A—C15—H15B107.7
H5DB—C5D—H5DC109.5N17—C16—C15110.7 (3)
O6—C6—C19114.1 (3)N17—C16—H16A109.5
O6—C6—C5113.4 (3)C15—C16—H16A109.5
C19—C6—C5110.0 (3)N17—C16—H16B109.5
O6—C6—C7106.3 (3)C15—C16—H16B109.5
C19—C6—C7107.5 (3)H16A—C16—H16B108.1
C5—C6—C7104.8 (3)C17—N17—C16111.7 (3)
C6A—O6—C6117.8 (3)C17—N17—C9113.2 (3)
O6—C6A—H6AA109.5C16—N17—C9111.3 (3)
O6—C6A—H6AB109.5N17—C17—H17A109.5
H6AA—C6A—H6AB109.5N17—C17—H17B109.5
O6—C6A—H6AC109.5H17A—C17—H17B109.5
H6AA—C6A—H6AC109.5N17—C17—H17C109.5
H6AB—C6A—H6AC109.5H17A—C17—H17C109.5
C7A—C7—C8113.0 (3)H17B—C17—H17C109.5
C7A—C7—C6110.0 (3)C19—C18—C14116.3 (4)
C8—C7—C6110.0 (3)C19—C18—H18A121.9
C7A—C7—H7A107.9C14—C18—H18A121.9
C8—C7—H7A107.9C18—C19—C6114.6 (3)
C6—C7—H7A107.9C18—C19—H19A122.7
O7—C7A—C7B122.4 (3)C6—C19—H19A122.7
O7—C7A—C7120.7 (3)

Experimental details

Crystal data
Chemical formulaC27H35NO4
Mr437.56
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)9.706 (5), 7.292 (3), 16.958 (8)
β (°) 104.519 (6)
V3)1161.8 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.64 × 0.18 × 0.06
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(Bruker, 2000)
Tmin, Tmax0.921, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
5557, 3701, 2014
Rint0.056
(sin θ/λ)max1)0.670
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.124, 0.97
No. of reflections3701
No. of parameters290
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.25

Computer programs: SMART (Bruker, 1999), SMART, SAINT (Bruker, 2000) and XPREP (Bruker, 1997), SHELXTL (Bruker, 2000), SHELXTL.

 

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