3β,17β-Di­acetoxy-16-(3-pyridyl­methyl­ene)­androst-5-ene monohydrate

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.

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


 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

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

Crystal data

C29H37NO4·H2O	F(000) = 1040
Mr = 481.61	Dx = 1.179 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 11.523 (2) Å	θ = 10–15°
b = 15.279 (4) Å	µ = 0.08 mm^−1
c = 15.409 (6) Å	T = 293 K
V = 2712.9 (14) Å^3	Plate, colourless
Z = 4	0.20 × 0.15 × 0.1 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	1783 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ω–2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = −8→18
Tmin = 0.984, Tmax = 0.992	l = −17→18
2783 measured reflections	2 standard reflections every 120 min
2697 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.181	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1135P)^2] where P = (Fo^2 + 2Fc^2)/3
2697 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.8986 (4)	0.7821 (4)	0.1810 (3)	0.0681 (14)
H1A	0.9620	0.7506	0.1539	0.082*
H1B	0.9209	0.8432	0.1845	0.082*
C2	0.8817 (5)	0.7472 (4)	0.2723 (4)	0.0795 (16)
H2A	0.8664	0.6848	0.2700	0.095*
H2B	0.9520	0.7563	0.3057	0.095*
C3	0.7816 (6)	0.7932 (4)	0.3158 (3)	0.0745 (15)
H3	0.7978	0.8559	0.3216	0.089*
C4	0.6714 (5)	0.7788 (3)	0.2644 (3)	0.0674 (13)
H4A	0.6078	0.8098	0.2919	0.081*
H4B	0.6525	0.7169	0.2640	0.081*
C5	0.6854 (4)	0.8110 (3)	0.1715 (3)	0.0556 (11)
C6	0.6109 (4)	0.8663 (3)	0.1387 (3)	0.0605 (12)
H6	0.5506	0.8852	0.1742	0.073*
C7	0.6155 (4)	0.9013 (3)	0.0478 (3)	0.0559 (11)
H7A	0.6421	0.9615	0.0494	0.067*
H7B	0.5380	0.9009	0.0234	0.067*
C8	0.6964 (3)	0.8479 (3)	−0.0108 (3)	0.0502 (10)
H8	0.6593	0.7925	−0.0271	0.060*
C9	0.8105 (4)	0.8299 (3)	0.0394 (3)	0.0537 (11)
H9	0.8393	0.8869	0.0591	0.064*
C10	0.7897 (4)	0.7745 (3)	0.1219 (3)	0.0548 (11)
C11	0.9044 (4)	0.7919 (4)	−0.0209 (3)	0.0674 (14)
H11A	0.9770	0.7891	0.0108	0.081*
H11B	0.8828	0.7325	−0.0361	0.081*
C12	0.9243 (4)	0.8437 (4)	−0.1046 (3)	0.0665 (14)
H12A	0.9563	0.9007	−0.0907	0.080*
H12B	0.9798	0.8130	−0.1409	0.080*
C13	0.8105 (3)	0.8550 (3)	−0.1538 (3)	0.0510 (10)
C14	0.7253 (3)	0.9019 (3)	−0.0928 (3)	0.0491 (10)
H14	0.7649	0.9549	−0.0727	0.059*
C15	0.6263 (3)	0.9326 (3)	−0.1517 (3)	0.0521 (10)
H15A	0.5643	0.8896	−0.1535	0.063*
H15B	0.5949	0.9880	−0.1319	0.063*
C16	0.6827 (3)	0.9421 (3)	−0.2390 (3)	0.0527 (11)
C17	0.8107 (3)	0.9211 (3)	−0.2279 (3)	0.0529 (11)
H17	0.8522	0.9740	−0.2096	0.064*
C18	0.7649 (4)	0.7672 (3)	−0.1872 (3)	0.0661 (13)
H18A	0.7648	0.7254	−0.1407	0.099*
H18B	0.8141	0.7465	−0.2331	0.099*
H18C	0.6873	0.7745	−0.2087	0.099*
C19	0.7671 (4)	0.6776 (3)	0.1013 (4)	0.0698 (13)
H19A	0.6994	0.6726	0.0653	0.105*
H19B	0.7548	0.6461	0.1544	0.105*
H19C	0.8328	0.6536	0.0714	0.105*
C20	0.6352 (4)	0.9583 (3)	−0.3168 (3)	0.0609 (13)
H20	0.6866	0.9581	−0.3634	0.073*
C21	0.5138 (4)	0.9763 (3)	−0.3389 (4)	0.0661 (13)
C22	0.4283 (4)	1.0032 (4)	−0.2832 (4)	0.0795 (16)
H22	0.4442	1.0107	−0.2245	0.095*
C23	0.3176 (5)	1.0190 (4)	−0.3153 (6)	0.102 (2)
H23	0.2589	1.0368	−0.2777	0.123*
C24	0.2946 (6)	1.0088 (6)	−0.4001 (6)	0.118 (3)
H24	0.2198	1.0196	−0.4200	0.142*
N25	0.3755 (5)	0.9837 (5)	−0.4568 (4)	0.114 (2)
C26	0.4809 (5)	0.9681 (4)	−0.4252 (4)	0.0842 (17)
H26	0.5376	0.9502	−0.4643	0.101*
O27	0.8585 (2)	0.8900 (2)	−0.3089 (2)	0.0648 (9)
C28	0.9691 (4)	0.9071 (4)	−0.3267 (3)	0.0665 (14)
O29	1.0310 (3)	0.9489 (3)	−0.2796 (3)	0.0914 (13)
C30	1.0064 (5)	0.8713 (5)	−0.4094 (3)	0.0941 (19)
H30A	0.9431	0.8406	−0.4360	0.141*
H30B	1.0698	0.8316	−0.4001	0.141*
H30C	1.0312	0.9180	−0.4467	0.141*
O31	0.7659 (4)	0.7528 (3)	0.4017 (2)	0.0887 (12)
C32	0.7367 (7)	0.8034 (4)	0.4671 (4)	0.0904 (19)
O33A	0.7006 (8)	0.8791 (6)	0.4571 (5)	0.089 (2)*	0.55
O33B	0.7611 (9)	0.8806 (6)	0.4656 (6)	0.082 (2)*	0.45
C34	0.7171 (6)	0.7490 (4)	0.5491 (3)	0.113 (2)
H34A	0.7327	0.6885	0.5368	0.169*
H34B	0.6381	0.7553	0.5678	0.169*
H34C	0.7683	0.7690	0.5941	0.169*
O1WA	0.4013 (6)	0.9166 (4)	0.3575 (3)	0.138 (3)*	0.68
O1WB	0.3258 (6)	0.9460 (4)	0.3719 (3)	0.146 (6)*	0.32

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.066 (3)	0.078 (3)	0.060 (3)	0.001 (2)	−0.009 (3)	0.009 (3)
C2	0.081 (3)	0.086 (4)	0.072 (4)	0.001 (3)	−0.021 (3)	0.015 (3)
C3	0.109 (4)	0.068 (3)	0.046 (3)	−0.010 (3)	−0.011 (3)	0.011 (2)
C4	0.079 (3)	0.064 (3)	0.060 (3)	−0.002 (3)	0.005 (3)	0.000 (3)
C5	0.059 (2)	0.064 (3)	0.044 (3)	−0.010 (2)	0.004 (2)	−0.001 (2)
C6	0.055 (2)	0.081 (3)	0.045 (3)	−0.001 (2)	0.013 (2)	0.002 (2)
C7	0.051 (2)	0.064 (3)	0.053 (3)	0.007 (2)	0.006 (2)	0.009 (2)
C8	0.042 (2)	0.063 (3)	0.045 (2)	−0.004 (2)	0.0043 (19)	−0.006 (2)
C9	0.041 (2)	0.063 (3)	0.057 (3)	−0.003 (2)	0.001 (2)	0.003 (2)
C10	0.053 (2)	0.063 (3)	0.048 (3)	−0.001 (2)	−0.001 (2)	0.001 (2)
C11	0.045 (2)	0.098 (4)	0.059 (3)	0.015 (2)	0.007 (2)	0.007 (3)
C12	0.042 (2)	0.100 (4)	0.057 (3)	0.011 (2)	0.003 (2)	0.010 (3)
C13	0.0404 (19)	0.054 (2)	0.059 (3)	0.0042 (18)	0.007 (2)	−0.011 (2)
C14	0.0419 (19)	0.058 (2)	0.047 (2)	0.0007 (18)	0.0057 (19)	0.001 (2)
C15	0.044 (2)	0.054 (2)	0.058 (3)	−0.0008 (19)	0.0070 (19)	0.000 (2)
C16	0.0399 (19)	0.062 (3)	0.056 (3)	−0.0059 (19)	0.004 (2)	0.002 (2)
C17	0.044 (2)	0.069 (3)	0.045 (3)	0.001 (2)	0.0070 (19)	−0.001 (2)
C18	0.077 (3)	0.068 (3)	0.053 (3)	0.011 (3)	0.013 (3)	0.002 (3)
C19	0.079 (3)	0.069 (3)	0.062 (3)	0.002 (3)	0.003 (3)	0.002 (3)
C20	0.048 (2)	0.073 (3)	0.062 (3)	−0.002 (2)	0.004 (2)	0.014 (3)
C21	0.054 (2)	0.072 (3)	0.073 (3)	−0.004 (2)	−0.002 (2)	0.018 (3)
C22	0.065 (3)	0.085 (4)	0.089 (4)	−0.001 (3)	−0.002 (3)	0.027 (3)
C23	0.052 (3)	0.111 (5)	0.144 (7)	−0.002 (3)	0.001 (4)	0.042 (5)
C24	0.073 (4)	0.151 (7)	0.131 (7)	−0.011 (5)	−0.040 (5)	0.060 (6)
N25	0.083 (3)	0.148 (6)	0.111 (5)	−0.018 (4)	−0.039 (4)	0.041 (4)
C26	0.084 (4)	0.099 (4)	0.069 (4)	−0.017 (3)	−0.027 (3)	0.023 (3)
O27	0.0530 (17)	0.091 (2)	0.0507 (19)	−0.0014 (16)	0.0094 (14)	−0.0044 (17)
C28	0.044 (2)	0.099 (4)	0.056 (3)	0.014 (3)	0.009 (2)	0.005 (3)
O29	0.0568 (19)	0.124 (3)	0.093 (3)	−0.002 (2)	0.023 (2)	−0.002 (3)
C30	0.074 (3)	0.152 (6)	0.057 (3)	0.024 (4)	0.018 (3)	0.008 (4)
O31	0.135 (3)	0.083 (2)	0.048 (2)	−0.013 (3)	−0.005 (2)	0.0021 (19)
C32	0.128 (5)	0.093 (4)	0.050 (3)	−0.021 (4)	−0.011 (4)	0.002 (3)
C34	0.157 (6)	0.129 (6)	0.052 (3)	−0.030 (6)	−0.009 (4)	0.000 (4)

Geometric parameters (Å, º)

C1—C2	1.517 (7)	C14—C15	1.532 (6)
C1—C10	1.554 (6)	C15—C16	1.501 (6)
C2—C3	1.508 (8)	C16—C20	1.341 (7)
C3—O31	1.471 (6)	C16—C17	1.519 (6)
C3—C4	1.513 (8)	C17—O27	1.446 (5)
C4—C5	1.521 (7)	C20—C21	1.466 (6)
C5—C6	1.306 (6)	C21—C22	1.370 (7)
C5—C10	1.530 (6)	C21—C26	1.388 (7)
C6—C7	1.501 (6)	C22—C23	1.390 (8)
C7—C8	1.534 (6)	C23—C24	1.343 (10)
C8—C14	1.546 (6)	C24—N25	1.334 (10)
C8—C9	1.549 (6)	N25—C26	1.330 (7)
C9—C11	1.539 (6)	O27—C28	1.329 (5)
C9—C10	1.546 (6)	C28—O29	1.202 (6)
C10—C19	1.536 (7)	C28—C30	1.451 (7)
C11—C12	1.530 (7)	O31—C32	1.313 (7)
C12—C13	1.525 (6)	C32—O33B	1.213 (11)
C13—C17	1.524 (6)	C32—O33A	1.239 (11)
C13—C18	1.530 (6)	C32—C34	1.529 (7)
C13—C14	1.537 (6)
C2—C1—C10	114.4 (4)	C18—C13—C14	113.3 (3)
C3—C2—C1	110.3 (4)	C15—C14—C13	104.9 (3)
O31—C3—C2	107.4 (5)	C15—C14—C8	119.2 (3)
O31—C3—C4	107.9 (5)	C13—C14—C8	112.9 (4)
C2—C3—C4	110.0 (4)	C16—C15—C14	103.8 (3)
C3—C4—C5	110.9 (4)	C20—C16—C15	130.0 (4)
C6—C5—C4	120.2 (4)	C20—C16—C17	122.4 (4)
C6—C5—C10	124.0 (4)	C15—C16—C17	107.4 (4)
C4—C5—C10	115.8 (4)	O27—C17—C16	110.0 (4)
C5—C6—C7	124.7 (4)	O27—C17—C13	115.4 (4)
C6—C7—C8	112.4 (4)	C16—C17—C13	102.9 (3)
C7—C8—C14	109.2 (3)	C16—C20—C21	129.1 (4)
C7—C8—C9	108.4 (3)	C22—C21—C26	115.5 (5)
C14—C8—C9	108.7 (3)	C22—C21—C20	126.7 (5)
C11—C9—C10	113.5 (4)	C26—C21—C20	117.8 (5)
C11—C9—C8	111.2 (4)	C21—C22—C23	119.3 (6)
C10—C9—C8	112.1 (3)	C24—C23—C22	120.5 (7)
C5—C10—C19	108.7 (4)	N25—C24—C23	122.2 (6)
C5—C10—C9	109.5 (4)	C26—N25—C24	116.7 (6)
C19—C10—C9	112.6 (4)	N25—C26—C21	125.7 (6)
C5—C10—C1	108.3 (4)	C28—O27—C17	118.6 (4)
C19—C10—C1	109.3 (4)	O29—C28—O27	123.3 (5)
C9—C10—C1	108.4 (3)	O29—C28—C30	123.7 (5)
C12—C11—C9	114.8 (4)	O27—C28—C30	113.1 (5)
C13—C12—C11	110.4 (4)	C32—O31—C3	118.4 (5)
C17—C13—C12	116.5 (3)	O33B—C32—O31	119.9 (7)
C17—C13—C18	109.3 (4)	O33A—C32—O31	122.7 (6)
C12—C13—C18	111.3 (4)	O33B—C32—C34	125.3 (7)
C17—C13—C14	98.6 (3)	O33A—C32—C34	124.1 (7)
C12—C13—C14	107.3 (4)	O31—C32—C34	110.6 (5)
C10—C1—C2—C3	−57.0 (6)	C9—C8—C14—C15	−176.9 (4)
C1—C2—C3—O31	176.8 (4)	C7—C8—C14—C13	177.5 (3)
C1—C2—C3—C4	59.7 (6)	C9—C8—C14—C13	59.4 (5)
O31—C3—C4—C5	−174.5 (4)	C13—C14—C15—C16	−26.4 (4)
C2—C3—C4—C5	−57.6 (6)	C8—C14—C15—C16	−153.9 (4)
C3—C4—C5—C6	−126.6 (5)	C14—C15—C16—C20	172.2 (5)
C3—C4—C5—C10	53.6 (6)	C14—C15—C16—C17	−2.4 (5)
C4—C5—C6—C7	−179.2 (4)	C20—C16—C17—O27	−21.2 (6)
C10—C5—C6—C7	0.6 (8)	C15—C16—C17—O27	153.9 (4)
C5—C6—C7—C8	15.5 (7)	C20—C16—C17—C13	−144.7 (4)
C6—C7—C8—C14	−163.3 (4)	C15—C16—C17—C13	30.4 (5)
C6—C7—C8—C9	−45.1 (5)	C12—C13—C17—O27	81.0 (5)
C7—C8—C9—C11	−169.2 (4)	C18—C13—C17—O27	−46.2 (5)
C14—C8—C9—C11	−50.7 (5)	C14—C13—C17—O27	−164.7 (3)
C7—C8—C9—C10	62.5 (5)	C12—C13—C17—C16	−159.2 (4)
C14—C8—C9—C10	−179.0 (4)	C18—C13—C17—C16	73.6 (4)
C6—C5—C10—C19	−108.7 (5)	C14—C13—C17—C16	−44.9 (4)
C4—C5—C10—C19	71.1 (5)	C15—C16—C20—C21	3.7 (9)
C6—C5—C10—C9	14.7 (6)	C17—C16—C20—C21	177.6 (5)
C4—C5—C10—C9	−165.5 (4)	C16—C20—C21—C22	18.7 (9)
C6—C5—C10—C1	132.7 (5)	C16—C20—C21—C26	−163.2 (5)
C4—C5—C10—C1	−47.5 (5)	C26—C21—C22—C23	0.7 (8)
C11—C9—C10—C5	−173.1 (4)	C20—C21—C22—C23	178.8 (5)
C8—C9—C10—C5	−46.0 (5)	C21—C22—C23—C24	−0.5 (10)
C11—C9—C10—C19	−52.0 (5)	C22—C23—C24—N25	−0.2 (12)
C8—C9—C10—C19	75.1 (5)	C23—C24—N25—C26	0.7 (12)
C11—C9—C10—C1	69.0 (5)	C24—N25—C26—C21	−0.5 (10)
C8—C9—C10—C1	−163.9 (4)	C22—C21—C26—N25	−0.2 (9)
C2—C1—C10—C5	49.1 (6)	C20—C21—C26—N25	−178.5 (6)
C2—C1—C10—C19	−69.2 (6)	C16—C17—O27—C28	148.4 (4)
C2—C1—C10—C9	167.8 (4)	C13—C17—O27—C28	−95.8 (5)
C10—C9—C11—C12	178.1 (4)	C17—O27—C28—O29	−1.7 (8)
C8—C9—C11—C12	50.7 (6)	C17—O27—C28—C30	179.3 (4)
C9—C11—C12—C13	−54.6 (6)	C2—C3—O31—C32	142.9 (6)
C11—C12—C13—C17	167.3 (4)	C4—C3—O31—C32	−98.6 (6)
C11—C12—C13—C18	−66.5 (5)	C3—O31—C32—O33B	−25.3 (12)
C11—C12—C13—C14	58.0 (5)	C3—O31—C32—O33A	14.1 (11)
C17—C13—C14—C15	44.3 (4)	C3—O31—C32—C34	176.5 (5)
C12—C13—C14—C15	165.6 (3)	C17—C16—C20—H20	−2.4
C18—C13—C14—C15	−71.1 (5)	C15—C16—C20—H20	−176.3
C17—C13—C14—C8	175.6 (3)	H14—C14—C13—C18	176.4
C12—C13—C14—C8	−63.1 (5)	H8—C8—C9—H9	−174.3
C18—C13—C14—C8	60.2 (5)	H9—C9—C10—C19	−168.8
C7—C8—C14—C15	−58.8 (5)	C19—C10—C13—C18	10.8 (3)