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In the title compound, C29H37NO4·H2O, an androst-5-ene steroid, rings A and C adopt chair conformations, while ring B is in a half-chair conformation. The five-membered ring D adopts an envelope conformation. The molecular packing is probably stabilized by intermolecular O—H...N and O—H...O hydrogen bonds involving the disordered water mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017932/ci6161sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017932/ci6161Isup2.hkl
Contains datablock I

CCDC reference: 200761

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • H-atom completeness 95%
  • Disorder in solvent or counterion
  • R factor = 0.062
  • wR factor = 0.181
  • Data-to-parameter ratio = 8.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_202 Alert C Isotropic non-H Atoms in Anion/Solvent = 1 PLAT_302 Alert C Anion/Solvent Disorder ....................... 50.00 Perc. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C29 H39 N1 O5 Atom count from the _atom_site data: C29 H37 N1 O5 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C29 H39 N O5 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 116.00 116.00 0.00 H 156.00 148.00 8.00 N 4.00 4.00 0.00 O 20.00 20.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional? REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 2697 Count of symmetry unique reflns 2701 Completeness (_total/calc) 99.85% 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

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: ZORTEP97 (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

3β,17β-Diacetoxy-16-(3-pyridylmethylene)androst-5-ene monohydrate top
Crystal data top
C29H37NO4·H2OF(000) = 1040
Mr = 481.61Dx = 1.179 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 11.523 (2) Åθ = 10–15°
b = 15.279 (4) ŵ = 0.08 mm1
c = 15.409 (6) ÅT = 293 K
V = 2712.9 (14) Å3Plate, colourless
Z = 40.20 × 0.15 × 0.1 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
1783 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω–2θ scansh = 013
Absorption correction: ψ scan
(North et al., 1968)
k = 818
Tmin = 0.984, Tmax = 0.992l = 1718
2783 measured reflections2 standard reflections every 120 min
2697 independent reflections intensity decay: none
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1135P)2]
where P = (Fo2 + 2Fc2)/3
2697 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.18 e Å3
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*/UeqOcc. (<1)
C10.8986 (4)0.7821 (4)0.1810 (3)0.0681 (14)
H1A0.96200.75060.15390.082*
H1B0.92090.84320.18450.082*
C20.8817 (5)0.7472 (4)0.2723 (4)0.0795 (16)
H2A0.86640.68480.27000.095*
H2B0.95200.75630.30570.095*
C30.7816 (6)0.7932 (4)0.3158 (3)0.0745 (15)
H30.79780.85590.32160.089*
C40.6714 (5)0.7788 (3)0.2644 (3)0.0674 (13)
H4A0.60780.80980.29190.081*
H4B0.65250.71690.26400.081*
C50.6854 (4)0.8110 (3)0.1715 (3)0.0556 (11)
C60.6109 (4)0.8663 (3)0.1387 (3)0.0605 (12)
H60.55060.88520.17420.073*
C70.6155 (4)0.9013 (3)0.0478 (3)0.0559 (11)
H7A0.64210.96150.04940.067*
H7B0.53800.90090.02340.067*
C80.6964 (3)0.8479 (3)0.0108 (3)0.0502 (10)
H80.65930.79250.02710.060*
C90.8105 (4)0.8299 (3)0.0394 (3)0.0537 (11)
H90.83930.88690.05910.064*
C100.7897 (4)0.7745 (3)0.1219 (3)0.0548 (11)
C110.9044 (4)0.7919 (4)0.0209 (3)0.0674 (14)
H11A0.97700.78910.01080.081*
H11B0.88280.73250.03610.081*
C120.9243 (4)0.8437 (4)0.1046 (3)0.0665 (14)
H12A0.95630.90070.09070.080*
H12B0.97980.81300.14090.080*
C130.8105 (3)0.8550 (3)0.1538 (3)0.0510 (10)
C140.7253 (3)0.9019 (3)0.0928 (3)0.0491 (10)
H140.76490.95490.07270.059*
C150.6263 (3)0.9326 (3)0.1517 (3)0.0521 (10)
H15A0.56430.88960.15350.063*
H15B0.59490.98800.13190.063*
C160.6827 (3)0.9421 (3)0.2390 (3)0.0527 (11)
C170.8107 (3)0.9211 (3)0.2279 (3)0.0529 (11)
H170.85220.97400.20960.064*
C180.7649 (4)0.7672 (3)0.1872 (3)0.0661 (13)
H18A0.76480.72540.14070.099*
H18B0.81410.74650.23310.099*
H18C0.68730.77450.20870.099*
C190.7671 (4)0.6776 (3)0.1013 (4)0.0698 (13)
H19A0.69940.67260.06530.105*
H19B0.75480.64610.15440.105*
H19C0.83280.65360.07140.105*
C200.6352 (4)0.9583 (3)0.3168 (3)0.0609 (13)
H200.68660.95810.36340.073*
C210.5138 (4)0.9763 (3)0.3389 (4)0.0661 (13)
C220.4283 (4)1.0032 (4)0.2832 (4)0.0795 (16)
H220.44421.01070.22450.095*
C230.3176 (5)1.0190 (4)0.3153 (6)0.102 (2)
H230.25891.03680.27770.123*
C240.2946 (6)1.0088 (6)0.4001 (6)0.118 (3)
H240.21981.01960.42000.142*
N250.3755 (5)0.9837 (5)0.4568 (4)0.114 (2)
C260.4809 (5)0.9681 (4)0.4252 (4)0.0842 (17)
H260.53760.95020.46430.101*
O270.8585 (2)0.8900 (2)0.3089 (2)0.0648 (9)
C280.9691 (4)0.9071 (4)0.3267 (3)0.0665 (14)
O291.0310 (3)0.9489 (3)0.2796 (3)0.0914 (13)
C301.0064 (5)0.8713 (5)0.4094 (3)0.0941 (19)
H30A0.94310.84060.43600.141*
H30B1.06980.83160.40010.141*
H30C1.03120.91800.44670.141*
O310.7659 (4)0.7528 (3)0.4017 (2)0.0887 (12)
C320.7367 (7)0.8034 (4)0.4671 (4)0.0904 (19)
O33A0.7006 (8)0.8791 (6)0.4571 (5)0.089 (2)*0.55
O33B0.7611 (9)0.8806 (6)0.4656 (6)0.082 (2)*0.45
C340.7171 (6)0.7490 (4)0.5491 (3)0.113 (2)
H34A0.73270.68850.53680.169*
H34B0.63810.75530.56780.169*
H34C0.76830.76900.59410.169*
O1WA0.4013 (6)0.9166 (4)0.3575 (3)0.138 (3)*0.68
O1WB0.3258 (6)0.9460 (4)0.3719 (3)0.146 (6)*0.32
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.066 (3)0.078 (3)0.060 (3)0.001 (2)0.009 (3)0.009 (3)
C20.081 (3)0.086 (4)0.072 (4)0.001 (3)0.021 (3)0.015 (3)
C30.109 (4)0.068 (3)0.046 (3)0.010 (3)0.011 (3)0.011 (2)
C40.079 (3)0.064 (3)0.060 (3)0.002 (3)0.005 (3)0.000 (3)
C50.059 (2)0.064 (3)0.044 (3)0.010 (2)0.004 (2)0.001 (2)
C60.055 (2)0.081 (3)0.045 (3)0.001 (2)0.013 (2)0.002 (2)
C70.051 (2)0.064 (3)0.053 (3)0.007 (2)0.006 (2)0.009 (2)
C80.042 (2)0.063 (3)0.045 (2)0.004 (2)0.0043 (19)0.006 (2)
C90.041 (2)0.063 (3)0.057 (3)0.003 (2)0.001 (2)0.003 (2)
C100.053 (2)0.063 (3)0.048 (3)0.001 (2)0.001 (2)0.001 (2)
C110.045 (2)0.098 (4)0.059 (3)0.015 (2)0.007 (2)0.007 (3)
C120.042 (2)0.100 (4)0.057 (3)0.011 (2)0.003 (2)0.010 (3)
C130.0404 (19)0.054 (2)0.059 (3)0.0042 (18)0.007 (2)0.011 (2)
C140.0419 (19)0.058 (2)0.047 (2)0.0007 (18)0.0057 (19)0.001 (2)
C150.044 (2)0.054 (2)0.058 (3)0.0008 (19)0.0070 (19)0.000 (2)
C160.0399 (19)0.062 (3)0.056 (3)0.0059 (19)0.004 (2)0.002 (2)
C170.044 (2)0.069 (3)0.045 (3)0.001 (2)0.0070 (19)0.001 (2)
C180.077 (3)0.068 (3)0.053 (3)0.011 (3)0.013 (3)0.002 (3)
C190.079 (3)0.069 (3)0.062 (3)0.002 (3)0.003 (3)0.002 (3)
C200.048 (2)0.073 (3)0.062 (3)0.002 (2)0.004 (2)0.014 (3)
C210.054 (2)0.072 (3)0.073 (3)0.004 (2)0.002 (2)0.018 (3)
C220.065 (3)0.085 (4)0.089 (4)0.001 (3)0.002 (3)0.027 (3)
C230.052 (3)0.111 (5)0.144 (7)0.002 (3)0.001 (4)0.042 (5)
C240.073 (4)0.151 (7)0.131 (7)0.011 (5)0.040 (5)0.060 (6)
N250.083 (3)0.148 (6)0.111 (5)0.018 (4)0.039 (4)0.041 (4)
C260.084 (4)0.099 (4)0.069 (4)0.017 (3)0.027 (3)0.023 (3)
O270.0530 (17)0.091 (2)0.0507 (19)0.0014 (16)0.0094 (14)0.0044 (17)
C280.044 (2)0.099 (4)0.056 (3)0.014 (3)0.009 (2)0.005 (3)
O290.0568 (19)0.124 (3)0.093 (3)0.002 (2)0.023 (2)0.002 (3)
C300.074 (3)0.152 (6)0.057 (3)0.024 (4)0.018 (3)0.008 (4)
O310.135 (3)0.083 (2)0.048 (2)0.013 (3)0.005 (2)0.0021 (19)
C320.128 (5)0.093 (4)0.050 (3)0.021 (4)0.011 (4)0.002 (3)
C340.157 (6)0.129 (6)0.052 (3)0.030 (6)0.009 (4)0.000 (4)
Geometric parameters (Å, º) top
C1—C21.517 (7)C14—C151.532 (6)
C1—C101.554 (6)C15—C161.501 (6)
C2—C31.508 (8)C16—C201.341 (7)
C3—O311.471 (6)C16—C171.519 (6)
C3—C41.513 (8)C17—O271.446 (5)
C4—C51.521 (7)C20—C211.466 (6)
C5—C61.306 (6)C21—C221.370 (7)
C5—C101.530 (6)C21—C261.388 (7)
C6—C71.501 (6)C22—C231.390 (8)
C7—C81.534 (6)C23—C241.343 (10)
C8—C141.546 (6)C24—N251.334 (10)
C8—C91.549 (6)N25—C261.330 (7)
C9—C111.539 (6)O27—C281.329 (5)
C9—C101.546 (6)C28—O291.202 (6)
C10—C191.536 (7)C28—C301.451 (7)
C11—C121.530 (7)O31—C321.313 (7)
C12—C131.525 (6)C32—O33B1.213 (11)
C13—C171.524 (6)C32—O33A1.239 (11)
C13—C181.530 (6)C32—C341.529 (7)
C13—C141.537 (6)
C2—C1—C10114.4 (4)C18—C13—C14113.3 (3)
C3—C2—C1110.3 (4)C15—C14—C13104.9 (3)
O31—C3—C2107.4 (5)C15—C14—C8119.2 (3)
O31—C3—C4107.9 (5)C13—C14—C8112.9 (4)
C2—C3—C4110.0 (4)C16—C15—C14103.8 (3)
C3—C4—C5110.9 (4)C20—C16—C15130.0 (4)
C6—C5—C4120.2 (4)C20—C16—C17122.4 (4)
C6—C5—C10124.0 (4)C15—C16—C17107.4 (4)
C4—C5—C10115.8 (4)O27—C17—C16110.0 (4)
C5—C6—C7124.7 (4)O27—C17—C13115.4 (4)
C6—C7—C8112.4 (4)C16—C17—C13102.9 (3)
C7—C8—C14109.2 (3)C16—C20—C21129.1 (4)
C7—C8—C9108.4 (3)C22—C21—C26115.5 (5)
C14—C8—C9108.7 (3)C22—C21—C20126.7 (5)
C11—C9—C10113.5 (4)C26—C21—C20117.8 (5)
C11—C9—C8111.2 (4)C21—C22—C23119.3 (6)
C10—C9—C8112.1 (3)C24—C23—C22120.5 (7)
C5—C10—C19108.7 (4)N25—C24—C23122.2 (6)
C5—C10—C9109.5 (4)C26—N25—C24116.7 (6)
C19—C10—C9112.6 (4)N25—C26—C21125.7 (6)
C5—C10—C1108.3 (4)C28—O27—C17118.6 (4)
C19—C10—C1109.3 (4)O29—C28—O27123.3 (5)
C9—C10—C1108.4 (3)O29—C28—C30123.7 (5)
C12—C11—C9114.8 (4)O27—C28—C30113.1 (5)
C13—C12—C11110.4 (4)C32—O31—C3118.4 (5)
C17—C13—C12116.5 (3)O33B—C32—O31119.9 (7)
C17—C13—C18109.3 (4)O33A—C32—O31122.7 (6)
C12—C13—C18111.3 (4)O33B—C32—C34125.3 (7)
C17—C13—C1498.6 (3)O33A—C32—C34124.1 (7)
C12—C13—C14107.3 (4)O31—C32—C34110.6 (5)
C10—C1—C2—C357.0 (6)C9—C8—C14—C15176.9 (4)
C1—C2—C3—O31176.8 (4)C7—C8—C14—C13177.5 (3)
C1—C2—C3—C459.7 (6)C9—C8—C14—C1359.4 (5)
O31—C3—C4—C5174.5 (4)C13—C14—C15—C1626.4 (4)
C2—C3—C4—C557.6 (6)C8—C14—C15—C16153.9 (4)
C3—C4—C5—C6126.6 (5)C14—C15—C16—C20172.2 (5)
C3—C4—C5—C1053.6 (6)C14—C15—C16—C172.4 (5)
C4—C5—C6—C7179.2 (4)C20—C16—C17—O2721.2 (6)
C10—C5—C6—C70.6 (8)C15—C16—C17—O27153.9 (4)
C5—C6—C7—C815.5 (7)C20—C16—C17—C13144.7 (4)
C6—C7—C8—C14163.3 (4)C15—C16—C17—C1330.4 (5)
C6—C7—C8—C945.1 (5)C12—C13—C17—O2781.0 (5)
C7—C8—C9—C11169.2 (4)C18—C13—C17—O2746.2 (5)
C14—C8—C9—C1150.7 (5)C14—C13—C17—O27164.7 (3)
C7—C8—C9—C1062.5 (5)C12—C13—C17—C16159.2 (4)
C14—C8—C9—C10179.0 (4)C18—C13—C17—C1673.6 (4)
C6—C5—C10—C19108.7 (5)C14—C13—C17—C1644.9 (4)
C4—C5—C10—C1971.1 (5)C15—C16—C20—C213.7 (9)
C6—C5—C10—C914.7 (6)C17—C16—C20—C21177.6 (5)
C4—C5—C10—C9165.5 (4)C16—C20—C21—C2218.7 (9)
C6—C5—C10—C1132.7 (5)C16—C20—C21—C26163.2 (5)
C4—C5—C10—C147.5 (5)C26—C21—C22—C230.7 (8)
C11—C9—C10—C5173.1 (4)C20—C21—C22—C23178.8 (5)
C8—C9—C10—C546.0 (5)C21—C22—C23—C240.5 (10)
C11—C9—C10—C1952.0 (5)C22—C23—C24—N250.2 (12)
C8—C9—C10—C1975.1 (5)C23—C24—N25—C260.7 (12)
C11—C9—C10—C169.0 (5)C24—N25—C26—C210.5 (10)
C8—C9—C10—C1163.9 (4)C22—C21—C26—N250.2 (9)
C2—C1—C10—C549.1 (6)C20—C21—C26—N25178.5 (6)
C2—C1—C10—C1969.2 (6)C16—C17—O27—C28148.4 (4)
C2—C1—C10—C9167.8 (4)C13—C17—O27—C2895.8 (5)
C10—C9—C11—C12178.1 (4)C17—O27—C28—O291.7 (8)
C8—C9—C11—C1250.7 (6)C17—O27—C28—C30179.3 (4)
C9—C11—C12—C1354.6 (6)C2—C3—O31—C32142.9 (6)
C11—C12—C13—C17167.3 (4)C4—C3—O31—C3298.6 (6)
C11—C12—C13—C1866.5 (5)C3—O31—C32—O33B25.3 (12)
C11—C12—C13—C1458.0 (5)C3—O31—C32—O33A14.1 (11)
C17—C13—C14—C1544.3 (4)C3—O31—C32—C34176.5 (5)
C12—C13—C14—C15165.6 (3)C17—C16—C20—H202.4
C18—C13—C14—C1571.1 (5)C15—C16—C20—H20176.3
C17—C13—C14—C8175.6 (3)H14—C14—C13—C18176.4
C12—C13—C14—C863.1 (5)H8—C8—C9—H9174.3
C18—C13—C14—C860.2 (5)H9—C9—C10—C19168.8
C7—C8—C14—C1558.8 (5)C19—C10—C13—C1810.8 (3)
 

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