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Molecular structural parameters of two potential drugs against Trypanosoma cruzi epimastigotes, 20-piperidin-2-yl-5α-pregnan-3β,20-diol (1) and 20-N-methylpiperidin-2-yl-5α-pregnan-3β, 20-diol (2) were studied using a combination of a stereoselective synthetic route, spectroscopic characterization and single-crystal X-ray analysis. Both compounds were synthesized with an R configuration at C20. This chirality is a consequence of the stereoselectivity observed during the formation of the intermediate 20-pyridin-2-yl-5α-pregnan-3β,20R-diol (4). NMR data indicated that the six-membered aza ring of (2) is conformationally more restrained, in CDCl3 solution, than (1). X-ray studies showed that maximum deviations among structural molecular parameters of (1) and (2) correspond to torsion angles along the C20—C22 bonds, leading to a different relative orientation of the N atom; a critical structural parameter for the binding properties of aza-sterols to Δ24(25) sterol methyl transferase. Cremer–Pople parameters of the five-membered rings of (1) and (2) lie in the observed range for a family of tetracyclic fused ring systems retrieved from the CSD. The φ2 parameter of (1) lies just on the mean of the family, while φ2 of (2) deviates significantly towards the lower limit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101013234/an0583sup1.cif
Contains datablocks 1, 2, global

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768101013234/an0583sup2.pdf
Supplementary material

CCDC references: 174982; 174983

Computing details top

For both compounds, data collection: MSC/AFC, Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC, Diffractometer Control Software (Molecular Structure Corporation, 1992); data reduction: TEXSAN, (Molecular Structure Corporation, 1992); program(s) used to solve structure: SIR92 (Altomare et al. 1994); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXL93 (Sheldrick, 1993).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
(1) top
Crystal data top
C26H45NO2·C2H3NDx = 1.091 Mg m3
Mr = 444.68Mo Kα radiation, λ = 0.71069 Å
Orthorhombic, P212121Cell parameters from 21 reflections
a = 13.384 (2) Åθ = 17–20°
b = 17.452 (3) ŵ = 0.07 mm1
c = 11.596 (3) ÅT = 293 K
V = 2708.4 (10) Å3Irregular block, colorless
Z = 40.75 × 0.60 × 0.55 mm
F(000) = 984
Data collection top
Rigaku AFC-7S
diffractometer
1881 reflections with I > 2σ(I)
Radiation source: normal focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω–2θ scansh = 015
Absorption correction: ψ scan
(North, Phillips & Mathews, 1968)'
k = 020
Tmin = 0.943, Tmax = 0.971l = 013
2689 measured reflections3 standard reflections every 150 reflections
2689 independent reflections intensity decay: 4%
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)] = 0.055See text
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.1144P)2] P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.025
2468 reflectionsΔρmax = 0.35 e Å3
290 parametersΔρmin = 0.18 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 3.61 (318)
Crystal data top
C26H45NO2·C2H3NV = 2708.4 (10) Å3
Mr = 444.68Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 13.384 (2) ŵ = 0.07 mm1
b = 17.452 (3) ÅT = 293 K
c = 11.596 (3) Å0.75 × 0.60 × 0.55 mm
Data collection top
Rigaku AFC-7S
diffractometer
1881 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North, Phillips & Mathews, 1968)'
Rint = 0.000
Tmin = 0.943, Tmax = 0.9713 standard reflections every 150 reflections
2689 measured reflections intensity decay: 4%
2689 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055See text
wR(F2) = 0.141Δρmax = 0.35 e Å3
S = 0.96Δρmin = 0.18 e Å3
2468 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
290 parametersAbsolute structure parameter: 3.61 (318)
0 restraints
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 on F2 for ALL reflections except for 221 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor_obs 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
O10.1475 (2)0.0600 (2)0.4845 (3)0.0590 (8)
H1O0.1398 (2)0.0881 (2)0.5609 (3)0.068 (2)*
O20.7357 (2)0.0792 (2)0.4732 (2)0.0547 (8)
H2O0.7786 (2)0.0333 (2)0.4765 (2)0.068 (2)*
N10.6684 (3)0.1572 (2)0.1848 (3)0.0504 (9)
H1N0.6007 (3)0.1645 (2)0.2021 (3)0.068 (2)*
N20.4487 (6)0.2587 (4)0.2113 (6)0.127 (2)
C10.1291 (3)0.0774 (3)0.4100 (4)0.0496 (10)
H1A0.1717 (3)0.1220 (3)0.4015 (4)0.068 (2)*
H1B0.1286 (3)0.0505 (3)0.3368 (4)0.068 (2)*
C20.0221 (3)0.1043 (3)0.4373 (4)0.0546 (11)
H2A0.0230 (3)0.1366 (3)0.5054 (4)0.068 (2)*
H2B0.0029 (3)0.1347 (3)0.3734 (4)0.068 (2)*
C30.0469 (3)0.0368 (3)0.4576 (4)0.0553 (11)
H30.0504 (3)0.0085 (3)0.3857 (4)0.068 (2)*
C40.0048 (3)0.0172 (2)0.5465 (4)0.0527 (11)
H4A0.0480 (3)0.0616 (2)0.5524 (4)0.068 (2)*
H4B0.0043 (3)0.0082 (2)0.6209 (4)0.068 (2)*
C50.1007 (3)0.0436 (2)0.5180 (4)0.0479 (10)
H50.0965 (3)0.0688 (2)0.4436 (4)0.068 (2)*
C60.1392 (3)0.1031 (2)0.6018 (5)0.0602 (13)
H6A0.0908 (3)0.1442 (2)0.6088 (5)0.068 (2)*
H6B0.1480 (3)0.0801 (2)0.6773 (5)0.068 (2)*
C70.2383 (3)0.1355 (2)0.5591 (4)0.0598 (12)
H7A0.2638 (3)0.1709 (2)0.6164 (4)0.068 (2)*
H7B0.2274 (3)0.1639 (2)0.4883 (4)0.068 (2)*
C80.3166 (3)0.0735 (2)0.5382 (3)0.0444 (10)
H80.3361 (3)0.0523 (2)0.6121 (3)0.068 (2)*
C90.2754 (3)0.0080 (2)0.4623 (3)0.0404 (9)
H90.2631 (3)0.0305 (2)0.3871 (3)0.068 (2)*
C100.1744 (3)0.0246 (2)0.5022 (3)0.0413 (9)
C110.3575 (3)0.0517 (2)0.4435 (4)0.0469 (10)
H11A0.3735 (3)0.0755 (2)0.5168 (4)0.068 (2)*
H11B0.3321 (3)0.0913 (2)0.3926 (4)0.068 (2)*
C120.4533 (3)0.0187 (2)0.3918 (4)0.0452 (10)
H12A0.4395 (3)0.0010 (2)0.3141 (4)0.068 (2)*
H12B0.5033 (3)0.0588 (2)0.3869 (4)0.068 (2)*
C130.4958 (3)0.0484 (2)0.4622 (3)0.0392 (9)
C140.4093 (3)0.1057 (2)0.4802 (3)0.0411 (9)
H140.3884 (3)0.1204 (2)0.4032 (3)0.068 (2)*
C150.4610 (3)0.1766 (2)0.5301 (4)0.0546 (11)
H15A0.4226 (3)0.2227 (2)0.5153 (4)0.068 (2)*
H15B0.4710 (3)0.1713 (2)0.6125 (4)0.068 (2)*
C160.5619 (3)0.1786 (2)0.4660 (4)0.0527 (11)
H16A0.5643 (3)0.2221 (2)0.4139 (4)0.068 (2)*
H16B0.6167 (3)0.1827 (2)0.5203 (4)0.068 (2)*
C170.5690 (3)0.1025 (2)0.3977 (3)0.0393 (9)
H170.5372 (3)0.1130 (2)0.3242 (3)0.068 (2)*
C180.5394 (4)0.0190 (3)0.5754 (4)0.0570 (12)
H18A0.5656 (4)0.0618 (3)0.6193 (4)0.068 (2)*
H18B0.4875 (4)0.0064 (3)0.6195 (4)0.068 (2)*
H18C0.5928 (4)0.0171 (3)0.5595 (4)0.068 (2)*
C190.1878 (3)0.0704 (2)0.6148 (4)0.0527 (11)
H19A0.1237 (3)0.0906 (2)0.6392 (4)0.068 (2)*
H19B0.2339 (3)0.1124 (2)0.6015 (4)0.068 (2)*
H19C0.2143 (3)0.0371 (2)0.6745 (4)0.068 (2)*
C200.6774 (3)0.0803 (2)0.3680 (3)0.0423 (9)
C210.6838 (3)0.0023 (2)0.3088 (4)0.0474 (10)
H21A0.7531 (3)0.0093 (2)0.2915 (4)0.068 (2)*
H21B0.6569 (3)0.0368 (2)0.3596 (4)0.068 (2)*
H21C0.6455 (3)0.0034 (2)0.2378 (4)0.068 (2)*
C220.7247 (3)0.1440 (2)0.2918 (4)0.0476 (10)
H220.7230 (3)0.1911 (2)0.3361 (4)0.068 (2)*
C230.8346 (3)0.1280 (3)0.2627 (4)0.0616 (13)
H23A0.8729 (3)0.1236 (3)0.3334 (4)0.068 (2)*
H23B0.8389 (3)0.0794 (3)0.2223 (4)0.068 (2)*
C240.8802 (4)0.1911 (3)0.1865 (5)0.0716 (15)
H24A0.9467 (4)0.1760 (3)0.1623 (5)0.068 (2)*
H24B0.8856 (4)0.2382 (3)0.2304 (5)0.068 (2)*
C250.8152 (4)0.2038 (3)0.0807 (5)0.0718 (15)
H25A0.8160 (4)0.1584 (3)0.0324 (5)0.068 (2)*
H25B0.8417 (4)0.2462 (3)0.0360 (5)0.068 (2)*
C260.7076 (4)0.2214 (3)0.1162 (4)0.0662 (13)
H26A0.6667 (4)0.2293 (3)0.0482 (4)0.068 (2)*
H26B0.7062 (4)0.2680 (3)0.1617 (4)0.068 (2)*
C270.3754 (6)0.2792 (4)0.2413 (6)0.085 (2)
C280.2775 (7)0.3019 (4)0.2731 (8)0.147 (4)
H28A0.2797 (7)0.3297 (4)0.3455 (8)0.068 (2)*
H28B0.2508 (7)0.3348 (4)0.2132 (8)0.068 (2)*
H28C0.2350 (7)0.2572 (4)0.2816 (8)0.068 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.044 (2)0.073 (2)0.061 (2)0.0032 (15)0.0048 (14)0.010 (2)
O20.053 (2)0.062 (2)0.049 (2)0.0080 (15)0.0137 (14)0.0088 (15)
N10.050 (2)0.049 (2)0.052 (2)0.002 (2)0.008 (2)0.003 (2)
N20.142 (6)0.135 (5)0.104 (4)0.022 (5)0.028 (5)0.012 (4)
C10.050 (2)0.048 (2)0.050 (2)0.000 (2)0.003 (2)0.006 (2)
C20.048 (3)0.057 (3)0.058 (3)0.004 (2)0.006 (2)0.008 (2)
C30.050 (2)0.062 (3)0.054 (3)0.003 (2)0.002 (2)0.014 (2)
C40.048 (2)0.051 (2)0.059 (3)0.011 (2)0.014 (2)0.010 (2)
C50.050 (2)0.043 (2)0.051 (2)0.004 (2)0.009 (2)0.004 (2)
C60.059 (3)0.043 (2)0.079 (3)0.002 (2)0.023 (3)0.009 (2)
C70.067 (3)0.036 (2)0.076 (3)0.000 (2)0.019 (3)0.013 (2)
C80.055 (2)0.038 (2)0.040 (2)0.001 (2)0.011 (2)0.004 (2)
C90.049 (2)0.036 (2)0.037 (2)0.004 (2)0.003 (2)0.003 (2)
C100.048 (2)0.038 (2)0.038 (2)0.003 (2)0.007 (2)0.002 (2)
C110.052 (2)0.033 (2)0.056 (3)0.002 (2)0.007 (2)0.005 (2)
C120.046 (2)0.036 (2)0.054 (2)0.002 (2)0.006 (2)0.008 (2)
C130.047 (2)0.037 (2)0.034 (2)0.006 (2)0.002 (2)0.001 (2)
C140.050 (2)0.033 (2)0.039 (2)0.001 (2)0.007 (2)0.001 (2)
C150.063 (3)0.042 (2)0.059 (3)0.001 (2)0.006 (2)0.013 (2)
C160.050 (2)0.044 (2)0.065 (3)0.004 (2)0.001 (2)0.015 (2)
C170.045 (2)0.035 (2)0.038 (2)0.002 (2)0.003 (2)0.003 (2)
C180.062 (3)0.062 (3)0.047 (2)0.004 (2)0.004 (2)0.013 (2)
C190.055 (2)0.053 (2)0.051 (2)0.000 (2)0.005 (2)0.008 (2)
C200.038 (2)0.044 (2)0.046 (2)0.003 (2)0.004 (2)0.007 (2)
C210.047 (2)0.043 (2)0.052 (2)0.006 (2)0.005 (2)0.002 (2)
C220.046 (2)0.044 (2)0.052 (2)0.000 (2)0.003 (2)0.011 (2)
C230.044 (2)0.073 (3)0.069 (3)0.001 (2)0.007 (2)0.010 (3)
C240.056 (3)0.069 (3)0.091 (4)0.016 (3)0.021 (3)0.009 (3)
C250.089 (4)0.055 (3)0.071 (3)0.020 (3)0.029 (3)0.005 (3)
C260.091 (4)0.047 (2)0.061 (3)0.009 (3)0.012 (3)0.002 (2)
C270.106 (5)0.081 (4)0.067 (4)0.019 (4)0.007 (4)0.008 (3)
C280.209 (10)0.090 (5)0.144 (7)0.003 (6)0.065 (7)0.022 (5)
Geometric parameters (Å, º) top
O1—C31.439 (5)C10—C191.542 (5)
O2—C201.448 (5)C11—C121.528 (5)
N1—C221.470 (6)C12—C131.537 (5)
N1—C261.471 (5)C13—C181.526 (5)
N2—C271.101 (9)C13—C141.543 (5)
C1—C21.540 (6)C13—C171.554 (5)
C1—C101.536 (6)C14—C151.531 (5)
C2—C31.516 (6)C15—C161.541 (6)
C3—C41.506 (6)C16—C171.548 (5)
C4—C51.522 (6)C17—C201.541 (5)
C5—C61.512 (6)C20—C211.526 (5)
C5—C101.556 (5)C20—C221.554 (6)
C6—C71.524 (6)C22—C231.534 (6)
C7—C81.525 (6)C23—C241.538 (7)
C8—C141.519 (5)C24—C251.520 (7)
C8—C91.545 (5)C25—C261.529 (7)
C9—C111.529 (5)C27—C281.418 (11)
C9—C101.538 (6)
C22—N1—C26113.1 (4)C18—C13—C14112.9 (3)
C2—C1—C10114.0 (4)C12—C13—C14106.8 (3)
C3—C2—C1111.2 (4)C18—C13—C17112.2 (3)
O1—C3—C4112.2 (4)C12—C13—C17116.1 (3)
O1—C3—C2112.6 (4)C14—C13—C1798.3 (3)
C4—C3—C2111.4 (4)C8—C14—C15120.0 (3)
C3—C4—C5112.9 (4)C8—C14—C13115.7 (3)
C6—C5—C4112.7 (3)C15—C14—C13103.6 (3)
C6—C5—C10112.6 (3)C14—C15—C16103.4 (3)
C4—C5—C10112.4 (3)C15—C16—C17106.3 (3)
C5—C6—C7110.0 (4)C20—C17—C16112.9 (3)
C8—C7—C6112.7 (3)C20—C17—C13123.3 (3)
C7—C8—C14111.7 (3)C16—C17—C13103.6 (3)
C7—C8—C9111.8 (3)O2—C20—C21109.7 (3)
C14—C8—C9108.2 (3)O2—C20—C17108.8 (3)
C11—C9—C8109.2 (3)C21—C20—C17112.2 (3)
C11—C9—C10115.0 (3)O2—C20—C22105.6 (3)
C8—C9—C10114.5 (3)C21—C20—C22111.0 (3)
C9—C10—C1111.0 (3)C17—C20—C22109.3 (3)
C9—C10—C19110.1 (3)N1—C22—C23109.5 (4)
C1—C10—C19108.9 (3)N1—C22—C20112.5 (3)
C9—C10—C5108.1 (3)C23—C22—C20112.7 (4)
C1—C10—C5106.9 (3)C22—C23—C24112.2 (4)
C19—C10—C5111.7 (3)C25—C24—C23110.0 (4)
C9—C11—C12113.7 (3)C26—C25—C24110.5 (4)
C11—C12—C13112.9 (3)N1—C26—C25109.3 (4)
C18—C13—C12110.0 (3)N2—C27—C28175.4 (9)
(2) top
Crystal data top
C27H47NO2F(000) = 464
Mr = 417.66Dx = 1.136 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71069 Å
a = 10.478 (3) ÅCell parameters from 25 reflections
b = 7.213 (2) Åθ = 16–20°
c = 16.384 (2) ŵ = 0.07 mm1
β = 99.58 (2)°T = 293 K
V = 1220.9 (6) Å3Needle, colorless
Z = 20.67 × 0.30 × 0.12 mm
Data collection top
Rigaku AFC-7S
diffractometer
3385 reflections with I > 2σ(I)
Radiation source: normal focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω–2θ scansh = 012
Absorption correction: ψ scan
(North, Phillips & Mathews, 1968)'
k = 88
Tmin = 0.96, Tmax = 1.00l = 1919
4569 measured reflections3 standard reflections every 150 reflections
4306 independent reflections intensity decay: 0.7%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullSee text
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0737P)2 + 0.1251P] P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116(Δ/σ)max = 0.031
S = 0.99Δρmax = 0.13 e Å3
4078 reflectionsΔρmin = 0.14 e Å3
274 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0233 (39)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.16 (205)
Crystal data top
C27H47NO2V = 1220.9 (6) Å3
Mr = 417.66Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.478 (3) ŵ = 0.07 mm1
b = 7.213 (2) ÅT = 293 K
c = 16.384 (2) Å0.67 × 0.30 × 0.12 mm
β = 99.58 (2)°
Data collection top
Rigaku AFC-7S
diffractometer
3385 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North, Phillips & Mathews, 1968)'
Rint = 0.022
Tmin = 0.96, Tmax = 1.003 standard reflections every 150 reflections
4569 measured reflections intensity decay: 0.7%
4306 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047See text
wR(F2) = 0.116Δρmax = 0.13 e Å3
S = 0.99Δρmin = 0.14 e Å3
4078 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
274 parametersAbsolute structure parameter: 0.16 (205)
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 on F2 for ALL reflections except for 228 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor_obs 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
O10.8422 (2)0.0229 (4)0.30124 (13)0.0908 (8)
H10.814 (3)0.061 (4)0.2694 (16)0.136*
O20.4859 (2)0.0978 (5)0.96198 (11)0.1007 (9)
H20.529 (3)0.002 (3)0.9678 (16)0.151*
N10.1765 (2)0.2471 (3)0.83192 (12)0.0553 (6)
C10.6823 (2)0.1231 (3)0.48184 (14)0.0467 (6)
H1A0.6794 (2)0.2419 (3)0.50926 (14)0.056*
H1B0.5941 (2)0.0878 (3)0.45948 (14)0.056*
C20.7585 (2)0.1445 (4)0.4108 (2)0.0570 (7)
H2A0.8450 (2)0.1884 (4)0.4324 (2)0.068*
H2B0.7166 (2)0.2365 (4)0.3721 (2)0.068*
C30.7672 (3)0.0349 (4)0.36631 (15)0.0608 (7)
H30.6794 (3)0.0750 (4)0.34266 (15)0.073*
C40.8286 (3)0.1817 (4)0.4259 (2)0.0561 (7)
H4A0.8288 (3)0.2989 (4)0.3969 (2)0.067*
H4B0.9177 (3)0.1479 (4)0.4464 (2)0.067*
C50.7564 (2)0.2053 (3)0.49912 (15)0.0446 (6)
H50.6686 (2)0.2446 (3)0.47528 (15)0.054*
C60.8111 (2)0.3583 (4)0.5578 (2)0.0530 (6)
H6A0.8186 (2)0.4709 (4)0.5266 (2)0.064*
H6B0.8972 (2)0.3238 (4)0.5851 (2)0.064*
C70.7253 (2)0.3956 (3)0.6232 (2)0.0534 (6)
H7A0.7685 (2)0.4838 (3)0.6632 (2)0.064*
H7B0.6448 (2)0.4513 (3)0.5966 (2)0.064*
C80.6948 (2)0.2213 (3)0.66856 (14)0.0419 (5)
H80.7739 (2)0.1811 (3)0.70490 (14)0.050*
C90.6477 (2)0.0613 (3)0.60816 (13)0.0376 (5)
H90.5671 (2)0.1054 (3)0.57476 (13)0.045*
C100.7406 (2)0.0219 (3)0.54581 (14)0.0380 (5)
C110.6101 (2)0.1084 (3)0.6548 (2)0.0484 (6)
H11A0.6873 (2)0.1588 (3)0.6884 (2)0.058*
H11B0.5752 (2)0.2026 (3)0.6150 (2)0.058*
C120.5103 (2)0.0653 (3)0.71061 (15)0.0470 (6)
H12A0.4293 (2)0.0294 (3)0.67654 (15)0.056*
H12B0.4946 (2)0.1762 (3)0.74090 (15)0.056*
C130.5559 (2)0.0906 (3)0.77214 (13)0.0427 (6)
C140.5907 (2)0.2568 (3)0.72159 (14)0.0423 (5)
H140.5118 (2)0.2856 (3)0.68248 (14)0.051*
C150.6071 (3)0.4156 (4)0.7842 (2)0.0595 (7)
H15A0.5968 (3)0.5349 (4)0.7565 (2)0.071*
H15B0.6913 (3)0.4108 (4)0.8192 (2)0.071*
C160.4982 (3)0.3809 (4)0.8344 (2)0.0636 (7)
H16A0.4290 (3)0.4701 (4)0.8193 (2)0.076*
H16B0.5309 (3)0.3930 (4)0.8931 (2)0.076*
C170.4477 (2)0.1821 (3)0.81437 (14)0.0441 (5)
H170.3732 (2)0.1965 (3)0.76996 (14)0.053*
C180.6714 (3)0.0263 (5)0.8361 (2)0.0686 (8)
H18A0.6987 (3)0.1255 (5)0.8741 (2)0.103*
H18B0.7416 (3)0.0084 (5)0.8083 (2)0.103*
H18C0.6463 (3)0.0784 (5)0.8660 (2)0.103*
C190.8720 (2)0.0501 (4)0.5909 (2)0.0524 (6)
H19A0.9095 (2)0.0395 (4)0.6312 (2)0.079*
H19B0.9290 (2)0.0698 (4)0.5514 (2)0.079*
H19C0.8595 (2)0.1650 (4)0.6181 (2)0.079*
C200.3935 (3)0.0879 (4)0.88575 (14)0.0567 (7)
C210.3672 (3)0.1179 (5)0.8711 (2)0.0785 (9)
H21A0.3336 (3)0.1693 (5)0.9173 (2)0.118*
H21B0.4463 (3)0.1799 (5)0.8653 (2)0.118*
H21C0.3051 (3)0.1343 (5)0.8215 (2)0.118*
C220.2735 (2)0.1989 (4)0.90441 (14)0.0528 (6)
H220.3091 (2)0.3185 (4)0.92555 (14)0.063*
C230.2118 (3)0.1187 (5)0.9751 (2)0.0754 (9)
H23A0.1711 (3)0.0010 (5)0.9581 (2)0.090*
H23B0.2784 (3)0.0965 (5)1.0228 (2)0.090*
C240.1113 (3)0.2511 (5)0.9990 (2)0.0815 (10)
H24A0.0701 (3)0.1955 (5)1.0418 (2)0.098*
H24B0.1530 (3)0.3650 (5)1.0206 (2)0.098*
C250.0117 (3)0.2930 (6)0.9249 (2)0.0858 (11)
H25A0.0506 (3)0.3814 (6)0.9395 (2)0.103*
H25B0.0343 (3)0.1805 (6)0.9053 (2)0.103*
C260.0792 (3)0.3738 (5)0.8566 (2)0.0811 (10)
H26A0.0146 (3)0.4014 (5)0.8085 (2)0.097*
H26B0.1211 (3)0.4892 (5)0.8760 (2)0.097*
C270.1140 (3)0.0935 (6)0.7846 (2)0.0887 (11)
H27A0.0529 (3)0.1400 (6)0.7390 (2)0.133*
H27B0.0696 (3)0.0186 (6)0.8195 (2)0.133*
H27C0.1779 (3)0.0197 (6)0.7640 (2)0.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.095 (2)0.122 (2)0.0656 (13)0.0443 (15)0.0427 (12)0.0312 (13)
O20.0622 (13)0.198 (3)0.0380 (10)0.019 (2)0.0024 (9)0.0213 (15)
N10.0483 (12)0.0739 (15)0.0458 (11)0.0053 (11)0.0139 (9)0.0047 (11)
C10.0434 (12)0.0478 (14)0.0498 (13)0.0058 (11)0.0100 (10)0.0068 (12)
C20.0467 (14)0.067 (2)0.058 (2)0.0087 (13)0.0104 (12)0.0242 (14)
C30.0537 (15)0.082 (2)0.0479 (14)0.0125 (14)0.0133 (12)0.0049 (14)
C40.0505 (14)0.065 (2)0.056 (2)0.0115 (13)0.0172 (12)0.0028 (13)
C50.0342 (11)0.0467 (14)0.0528 (13)0.0012 (10)0.0070 (10)0.0030 (11)
C60.0508 (14)0.0453 (14)0.068 (2)0.0101 (12)0.0255 (13)0.0054 (13)
C70.0509 (14)0.0449 (15)0.068 (2)0.0084 (12)0.0201 (12)0.0105 (13)
C80.0350 (11)0.0451 (14)0.0460 (13)0.0009 (10)0.0075 (10)0.0038 (10)
C90.0319 (11)0.0366 (12)0.0438 (12)0.0037 (9)0.0049 (9)0.0005 (10)
C100.0298 (10)0.0410 (12)0.0427 (11)0.0014 (9)0.0042 (9)0.0036 (10)
C110.0515 (13)0.0401 (13)0.0562 (14)0.0042 (11)0.0158 (12)0.0011 (12)
C120.0538 (14)0.0393 (13)0.0502 (14)0.0002 (11)0.0155 (11)0.0028 (11)
C130.0348 (12)0.0535 (14)0.0388 (11)0.0035 (11)0.0031 (10)0.0037 (11)
C140.0363 (12)0.0433 (13)0.0469 (12)0.0003 (10)0.0051 (10)0.0076 (11)
C150.059 (2)0.061 (2)0.062 (2)0.0114 (13)0.0203 (13)0.0189 (14)
C160.062 (2)0.074 (2)0.058 (2)0.0138 (15)0.0211 (13)0.0231 (14)
C170.0422 (12)0.0536 (14)0.0357 (11)0.0012 (11)0.0043 (10)0.0011 (11)
C180.0510 (15)0.095 (2)0.057 (2)0.0168 (15)0.0008 (13)0.017 (2)
C190.0363 (12)0.062 (2)0.0579 (15)0.0116 (11)0.0036 (11)0.0086 (13)
C200.0573 (15)0.083 (2)0.0294 (11)0.0073 (14)0.0059 (11)0.0108 (13)
C210.094 (2)0.068 (2)0.082 (2)0.018 (2)0.042 (2)0.031 (2)
C220.0539 (14)0.070 (2)0.0360 (12)0.0091 (13)0.0131 (11)0.0091 (12)
C230.084 (2)0.102 (2)0.0465 (15)0.006 (2)0.0296 (15)0.001 (2)
C240.093 (2)0.098 (2)0.066 (2)0.021 (2)0.048 (2)0.022 (2)
C250.074 (2)0.101 (3)0.095 (2)0.003 (2)0.048 (2)0.019 (2)
C260.071 (2)0.101 (3)0.080 (2)0.019 (2)0.037 (2)0.003 (2)
C270.066 (2)0.130 (3)0.068 (2)0.015 (2)0.004 (2)0.035 (2)
Geometric parameters (Å, º) top
O1—C31.429 (3)C13—C181.535 (3)
O1—H10.82C13—C141.535 (3)
O2—C201.449 (3)C13—C171.568 (3)
O2—H20.82C14—C151.528 (3)
N1—C271.445 (4)C14—H140.98
N1—C221.471 (3)C15—C161.533 (4)
N1—C261.475 (4)C15—H15A0.97
C1—C21.525 (3)C15—H15B0.97
C1—C101.534 (3)C16—C171.544 (4)
C1—H1A0.97C16—H16A0.97
C1—H1B0.97C16—H16B0.97
C2—C31.495 (4)C17—C201.540 (3)
C2—H2A0.97C17—H170.98
C2—H2B0.97C18—H18A0.96
C3—C41.510 (4)C18—H18B0.96
C3—H30.98C18—H18C0.96
C4—C51.529 (3)C19—H19A0.96
C4—H4A0.97C19—H19B0.96
C4—H4B0.97C19—H19C0.96
C5—C61.513 (3)C20—C211.522 (5)
C5—C101.551 (3)C20—C221.563 (4)
C5—H50.98C21—H21A0.96
C6—C71.533 (3)C21—H21B0.96
C6—H6A0.97C21—H21C0.96
C6—H6B0.97C22—C231.532 (4)
C7—C81.521 (3)C22—H220.98
C7—H7A0.97C23—C241.520 (5)
C7—H7B0.97C23—H23A0.97
C8—C141.525 (3)C23—H23B0.97
C8—C91.546 (3)C24—C251.494 (5)
C8—H80.98C24—H24A0.97
C9—C111.529 (3)C24—H24B0.97
C9—C101.550 (3)C25—C261.535 (5)
C9—H90.98C25—H25A0.97
C10—C191.540 (3)C25—H25B0.97
C11—C121.531 (3)C26—H26A0.97
C11—H11A0.97C26—H26B0.97
C11—H11B0.97C27—H27A0.96
C12—C131.533 (3)C27—H27B0.96
C12—H12A0.97C27—H27C0.96
C12—H12B0.97
C3—O1—H1109.47 (14)C15—C14—C13103.5 (2)
C20—O2—H2109.5 (2)C8—C14—C13115.7 (2)
C27—N1—C22116.3 (2)C15—C14—H14105.56 (14)
C27—N1—C26110.5 (2)C8—C14—H14105.56 (12)
C22—N1—C26110.0 (2)C13—C14—H14105.56 (12)
C2—C1—C10113.0 (2)C14—C15—C16103.1 (2)
C2—C1—H1A108.98 (15)C14—C15—H15A111.14 (14)
C10—C1—H1A108.98 (13)C16—C15—H15A111.1 (2)
C2—C1—H1B108.98 (13)C14—C15—H15B111.14 (14)
C10—C1—H1B108.98 (12)C16—C15—H15B111.1 (2)
H1A—C1—H1B107.8H15A—C15—H15B109.1
C3—C2—C1111.5 (2)C15—C16—C17107.3 (2)
C3—C2—H2A109.32 (15)C15—C16—H16A110.3 (2)
C1—C2—H2A109.32 (14)C17—C16—H16A110.26 (14)
C3—C2—H2B109.32 (14)C15—C16—H16B110.26 (14)
C1—C2—H2B109.32 (13)C17—C16—H16B110.26 (14)
H2A—C2—H2B108.0H16A—C16—H16B108.5
O1—C3—C2113.4 (3)C20—C17—C16113.9 (2)
O1—C3—C4107.3 (2)C20—C17—C13122.3 (2)
C2—C3—C4110.2 (2)C16—C17—C13103.7 (2)
O1—C3—H3108.6 (2)C20—C17—H17105.18 (13)
C2—C3—H3108.61 (15)C16—C17—H17105.18 (15)
C4—C3—H3108.6 (2)C13—C17—H17105.18 (11)
C3—C4—C5111.8 (2)C13—C18—H18A109.5 (2)
C3—C4—H4A109.25 (15)C13—C18—H18B109.47 (14)
C5—C4—H4A109.25 (14)H18A—C18—H18B109.5
C3—C4—H4B109.2 (2)C13—C18—H18C109.47 (15)
C5—C4—H4B109.25 (13)H18A—C18—H18C109.5
H4A—C4—H4B107.9H18B—C18—H18C109.5
C6—C5—C4113.3 (2)C10—C19—H19A109.47 (13)
C6—C5—C10111.7 (2)C10—C19—H19B109.47 (12)
C4—C5—C10113.5 (2)H19A—C19—H19B109.5
C6—C5—H5105.86 (13)C10—C19—H19C109.47 (13)
C4—C5—H5105.86 (13)H19A—C19—H19C109.5
C10—C5—H5105.86 (11)H19B—C19—H19C109.5
C5—C6—C7111.6 (2)O2—C20—C21105.1 (3)
C5—C6—H6A109.30 (14)O2—C20—C17110.8 (2)
C7—C6—H6A109.30 (14)C21—C20—C17113.0 (2)
C5—C6—H6B109.30 (13)O2—C20—C22104.5 (2)
C7—C6—H6B109.30 (14)C21—C20—C22113.6 (2)
H6A—C6—H6B108.0C17—C20—C22109.4 (2)
C8—C7—C6113.1 (2)C20—C21—H21A109.47 (14)
C8—C7—H7A108.97 (13)C20—C21—H21B109.5 (2)
C6—C7—H7A108.97 (13)H21A—C21—H21B109.5
C8—C7—H7B108.97 (13)C20—C21—H21C109.5 (2)
C6—C7—H7B108.97 (14)H21A—C21—H21C109.5
H7A—C7—H7B107.8H21B—C21—H21C109.5
C7—C8—C14111.6 (2)N1—C22—C23112.2 (2)
C7—C8—C9112.0 (2)N1—C22—C20115.7 (2)
C14—C8—C9107.9 (2)C23—C22—C20114.2 (2)
C7—C8—H8108.42 (13)N1—C22—H22104.40 (14)
C14—C8—H8108.42 (12)C23—C22—H22104.4 (2)
C9—C8—H8108.42 (11)C20—C22—H22104.40 (15)
C11—C9—C8111.0 (2)C24—C23—C22110.8 (3)
C11—C9—C10115.1 (2)C24—C23—H23A109.5 (2)
C8—C9—C10113.0 (2)C22—C23—H23A109.5 (2)
C11—C9—H9105.60 (12)C24—C23—H23B109.5 (2)
C8—C9—H9105.60 (11)C22—C23—H23B109.5 (2)
C10—C9—H9105.60 (11)H23A—C23—H23B108.1
C1—C10—C19108.7 (2)C25—C24—C23109.8 (3)
C1—C10—C9110.7 (2)C25—C24—H24A109.7 (2)
C19—C10—C9110.8 (2)C23—C24—H24A109.7 (2)
C1—C10—C5107.9 (2)C25—C24—H24B109.7 (2)
C19—C10—C5111.3 (2)C23—C24—H24B109.7 (2)
C9—C10—C5107.4 (2)H24A—C24—H24B108.2
C9—C11—C12113.2 (2)C24—C25—C26108.9 (3)
C9—C11—H11A108.93 (12)C24—C25—H25A109.9 (2)
C12—C11—H11A108.93 (13)C26—C25—H25A109.9 (2)
C9—C11—H11B108.93 (12)C24—C25—H25B109.9 (2)
C12—C11—H11B108.93 (13)C26—C25—H25B109.9 (2)
H11A—C11—H11B107.7H25A—C25—H25B108.3
C13—C12—C11111.9 (2)N1—C26—C25112.8 (3)
C13—C12—H12A109.24 (12)N1—C26—H26A109.0 (2)
C11—C12—H12A109.24 (13)C25—C26—H26A109.0 (2)
C13—C12—H12B109.24 (12)N1—C26—H26B109.0 (2)
C11—C12—H12B109.24 (13)C25—C26—H26B109.0 (2)
H12A—C12—H12B107.9H26A—C26—H26B107.8
C12—C13—C18110.6 (2)N1—C27—H27A109.5 (2)
C12—C13—C14107.1 (2)N1—C27—H27B109.5 (2)
C18—C13—C14111.9 (2)H27A—C27—H27B109.5
C12—C13—C17115.5 (2)N1—C27—H27C109.5 (2)
C18—C13—C17111.8 (2)H27A—C27—H27C109.5
C14—C13—C1799.4 (2)H27B—C27—H27C109.5
C15—C14—C8119.8 (2)

Experimental details

(1)(2)
Crystal data
Chemical formulaC26H45NO2·C2H3NC27H47NO2
Mr444.68417.66
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21
Temperature (K)293293
a, b, c (Å)13.384 (2), 17.452 (3), 11.596 (3)10.478 (3), 7.213 (2), 16.384 (2)
α, β, γ (°)90, 90, 9090, 99.58 (2), 90
V3)2708.4 (10)1220.9 (6)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.070.07
Crystal size (mm)0.75 × 0.60 × 0.550.67 × 0.30 × 0.12
Data collection
DiffractometerRigaku AFC-7S
diffractometer
Rigaku AFC-7S
diffractometer
Absorption correctionψ scan
(North, Phillips & Mathews, 1968)'
ψ scan
(North, Phillips & Mathews, 1968)'
Tmin, Tmax0.943, 0.9710.96, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
2689, 2689, 1881 4569, 4306, 3385
Rint0.0000.022
(sin θ/λ)max1)0.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.141, 0.96 0.047, 0.116, 0.99
No. of reflections24684078
No. of parameters290274
No. of restraints01
H-atom treatmentSee textSee text
Δρmax, Δρmin (e Å3)0.35, 0.180.13, 0.14
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter3.61 (318)0.16 (205)

Computer programs: MSC/AFC, Diffractometer Control Software (Molecular Structure Corporation, 1992), TEXSAN, (Molecular Structure Corporation, 1992), SIR92 (Altomare et al. 1994), SHELXL93 (Sheldrick, 1993), SHELXTL (Siemens, 1994).

 

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