The ring conformation of the title compound, C19H30O3, is similar to that of the 5α-epimer except for the cis A/B ring junction. Ring D adopts a 13β,14α-half chair conformation. The molecules are linked together by a two-dimensional network of hydrogen bonds involving the carbonyl and hydroxyl groups.
Supporting information
CCDC reference: 202986
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.108
- Data-to-parameter ratio = 8.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 71.86
From the CIF: _reflns_number_total 1827
Count of symmetry unique reflns 1823
Completeness (_total/calc) 100.22%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 4
Fraction of Friedel pairs measured 0.002
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.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
3
α,4
β-Dihydroxy-5
β-androstan-17-one
top
Crystal data top
C19H30O3 | F(000) = 336 |
Mr = 306.43 | Dx = 1.178 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 9.798 (3) Å | θ = 17.4–31.4° |
b = 7.7742 (11) Å | µ = 0.61 mm−1 |
c = 11.372 (4) Å | T = 293 K |
β = 94.36 (2)° | Prism, colourless |
V = 863.7 (4) Å3 | 0.48 × 0.37 × 0.37 mm |
Z = 2 | |
Data collection top
Enraf-Nonius MACH-3 diffractometer | 1794 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 71.9°, θmin = 4.5° |
profile data from ω–2θ scans | h = −12→12 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→9 |
Tmin = 0.713, Tmax = 0.798 | l = −14→14 |
3519 measured reflections | 3 standard reflections every 120 min |
1827 independent reflections | intensity decay: 1.6% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.1172P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1827 reflections | Δρmax = 0.24 e Å−3 |
208 parameters | Δρmin = −0.13 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0148 (16) |
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 | x | y | z | Uiso*/Ueq | |
C5 | 0.6590 (2) | 0.8913 (3) | 0.09577 (17) | 0.0393 (5) | |
H5 | 0.5914 | 0.9000 | 0.0280 | 0.047* | |
C8 | 0.6937 (2) | 0.8417 (3) | 0.35681 (17) | 0.0393 (4) | |
H8 | 0.5982 | 0.8369 | 0.3767 | 0.047* | |
C10 | 0.6286 (2) | 1.0404 (3) | 0.18075 (18) | 0.0412 (5) | |
C9 | 0.71918 (19) | 1.0176 (3) | 0.29831 (17) | 0.0377 (4) | |
H9 | 0.8141 | 1.0151 | 0.2768 | 0.045* | |
C14 | 0.7863 (2) | 0.8282 (3) | 0.47018 (17) | 0.0427 (5) | |
H14 | 0.8802 | 0.8386 | 0.4467 | 0.051* | |
C4 | 0.8009 (2) | 0.9046 (3) | 0.04730 (18) | 0.0415 (5) | |
H4A | 0.8713 | 0.8838 | 0.1116 | 0.050* | |
C2 | 0.8014 (3) | 1.2245 (3) | 0.0772 (2) | 0.0564 (6) | |
H2A | 0.8117 | 1.3336 | 0.0376 | 0.068* | |
H2B | 0.8686 | 1.2195 | 0.1443 | 0.068* | |
C13 | 0.7677 (2) | 0.9756 (3) | 0.55664 (18) | 0.0478 (5) | |
O4 | 0.81106 (18) | 0.7760 (3) | −0.04109 (14) | 0.0560 (4) | |
H4 | 0.882 (3) | 0.720 (5) | −0.027 (3) | 0.067* | |
C7 | 0.7187 (3) | 0.6958 (3) | 0.27182 (19) | 0.0501 (5) | |
H7A | 0.6938 | 0.5877 | 0.3071 | 0.060* | |
H7B | 0.8156 | 0.6910 | 0.2597 | 0.060* | |
C3 | 0.8253 (2) | 1.0783 (3) | −0.00657 (19) | 0.0500 (5) | |
H3A | 0.7625 | 1.0918 | −0.0772 | 0.060* | |
C11 | 0.7100 (3) | 1.1684 (3) | 0.3847 (2) | 0.0575 (6) | |
H11A | 0.7370 | 1.2732 | 0.3464 | 0.069* | |
H11B | 0.6155 | 1.1818 | 0.4031 | 0.069* | |
C1 | 0.6584 (3) | 1.2112 (3) | 0.1192 (2) | 0.0524 (6) | |
H1A | 0.5925 | 1.2255 | 0.0519 | 0.063* | |
H1B | 0.6452 | 1.3049 | 0.1735 | 0.063* | |
O3 | 0.96245 (19) | 1.0895 (3) | −0.04020 (16) | 0.0714 (6) | |
H3 | 0.964 (3) | 1.028 (5) | −0.101 (3) | 0.086* | |
C12 | 0.7998 (3) | 1.1453 (3) | 0.4999 (2) | 0.0600 (7) | |
H12A | 0.8956 | 1.1481 | 0.4837 | 0.072* | |
H12B | 0.7833 | 1.2388 | 0.5534 | 0.072* | |
O17 | 0.9401 (2) | 1.0066 (4) | 0.72026 (15) | 0.0961 (9) | |
C6 | 0.6381 (2) | 0.7152 (3) | 0.15269 (19) | 0.0482 (5) | |
H6A | 0.5415 | 0.6994 | 0.1629 | 0.058* | |
H6B | 0.6659 | 0.6258 | 0.1001 | 0.058* | |
C19 | 0.4744 (2) | 1.0405 (4) | 0.2014 (2) | 0.0601 (6) | |
H19A | 0.4547 | 1.1350 | 0.2517 | 0.072* | |
H19B | 0.4511 | 0.9343 | 0.2381 | 0.072* | |
H19C | 0.4217 | 1.0521 | 0.1271 | 0.072* | |
C15 | 0.7844 (3) | 0.6653 (4) | 0.5463 (2) | 0.0597 (7) | |
H15A | 0.8310 | 0.5710 | 0.5105 | 0.072* | |
H15B | 0.6913 | 0.6306 | 0.5581 | 0.072* | |
C18 | 0.6248 (2) | 0.9804 (4) | 0.6062 (2) | 0.0619 (7) | |
H18A | 0.6100 | 0.8754 | 0.6477 | 0.074* | |
H18B | 0.5556 | 0.9930 | 0.5424 | 0.074* | |
H18C | 0.6204 | 1.0759 | 0.6593 | 0.074* | |
C17 | 0.8664 (3) | 0.9151 (5) | 0.65769 (19) | 0.0622 (8) | |
C16 | 0.8608 (3) | 0.7202 (5) | 0.6632 (2) | 0.0673 (8) | |
H16A | 0.8121 | 0.6826 | 0.7297 | 0.081* | |
H16B | 0.9524 | 0.6719 | 0.6706 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C5 | 0.0394 (9) | 0.0402 (11) | 0.0366 (9) | 0.0002 (8) | −0.0076 (7) | −0.0021 (8) |
C8 | 0.0414 (9) | 0.0383 (10) | 0.0376 (9) | −0.0009 (8) | −0.0010 (7) | −0.0010 (8) |
C10 | 0.0408 (9) | 0.0402 (11) | 0.0418 (10) | 0.0084 (8) | −0.0024 (7) | −0.0016 (9) |
C9 | 0.0428 (9) | 0.0353 (9) | 0.0344 (9) | 0.0008 (8) | −0.0012 (7) | −0.0022 (8) |
C14 | 0.0399 (9) | 0.0508 (13) | 0.0372 (9) | −0.0008 (9) | 0.0016 (7) | 0.0024 (9) |
C4 | 0.0413 (10) | 0.0461 (11) | 0.0358 (9) | 0.0029 (9) | −0.0051 (7) | −0.0069 (8) |
C2 | 0.0800 (16) | 0.0428 (12) | 0.0456 (11) | −0.0107 (12) | 0.0003 (10) | 0.0040 (10) |
C13 | 0.0478 (11) | 0.0611 (15) | 0.0349 (10) | −0.0103 (10) | 0.0061 (8) | −0.0049 (10) |
O4 | 0.0577 (9) | 0.0632 (11) | 0.0461 (8) | 0.0101 (8) | −0.0032 (7) | −0.0183 (8) |
C7 | 0.0730 (15) | 0.0321 (10) | 0.0442 (11) | 0.0022 (10) | −0.0019 (10) | 0.0013 (9) |
C3 | 0.0530 (11) | 0.0578 (14) | 0.0384 (10) | −0.0095 (11) | −0.0019 (8) | −0.0017 (10) |
C11 | 0.0865 (17) | 0.0390 (12) | 0.0472 (11) | 0.0001 (12) | 0.0064 (11) | −0.0068 (10) |
C1 | 0.0678 (14) | 0.0409 (12) | 0.0470 (11) | 0.0123 (11) | −0.0051 (10) | 0.0033 (10) |
O3 | 0.0659 (10) | 0.0956 (17) | 0.0539 (9) | −0.0321 (11) | 0.0128 (8) | −0.0169 (11) |
C12 | 0.0825 (18) | 0.0575 (15) | 0.0404 (11) | −0.0216 (13) | 0.0070 (11) | −0.0126 (11) |
O17 | 0.0907 (14) | 0.149 (3) | 0.0454 (9) | −0.0525 (16) | −0.0154 (9) | 0.0034 (13) |
C6 | 0.0599 (13) | 0.0401 (11) | 0.0434 (11) | −0.0082 (10) | −0.0045 (9) | −0.0064 (9) |
C19 | 0.0444 (11) | 0.0763 (18) | 0.0588 (13) | 0.0158 (12) | −0.0003 (9) | −0.0008 (13) |
C15 | 0.0658 (15) | 0.0648 (16) | 0.0479 (12) | 0.0061 (12) | −0.0005 (11) | 0.0126 (12) |
C18 | 0.0556 (13) | 0.0765 (18) | 0.0552 (13) | −0.0017 (13) | 0.0155 (10) | −0.0070 (13) |
C17 | 0.0521 (13) | 0.103 (2) | 0.0318 (10) | −0.0191 (14) | 0.0064 (9) | −0.0003 (12) |
C16 | 0.0605 (15) | 0.099 (2) | 0.0424 (12) | 0.0100 (15) | 0.0017 (10) | 0.0152 (14) |
Geometric parameters (Å, º) top
C5—C6 | 1.535 (3) | C7—H7A | 0.9700 |
C5—C4 | 1.537 (3) | C7—H7B | 0.9700 |
C5—C10 | 1.552 (3) | C3—O3 | 1.428 (3) |
C5—H5 | 0.9800 | C3—H3A | 0.9800 |
C8—C7 | 1.522 (3) | C11—C12 | 1.532 (4) |
C8—C14 | 1.523 (3) | C11—H11A | 0.9700 |
C8—C9 | 1.549 (3) | C11—H11B | 0.9700 |
C8—H8 | 0.9800 | C1—H1A | 0.9700 |
C10—C1 | 1.539 (3) | C1—H1B | 0.9700 |
C10—C19 | 1.547 (3) | O3—H3 | 0.84 (4) |
C10—C9 | 1.557 (3) | C12—H12A | 0.9700 |
C9—C11 | 1.536 (3) | C12—H12B | 0.9700 |
C9—H9 | 0.9800 | O17—C17 | 1.207 (3) |
C14—C13 | 1.529 (3) | C6—H6A | 0.9700 |
C14—C15 | 1.535 (3) | C6—H6B | 0.9700 |
C14—H14 | 0.9800 | C19—H19A | 0.9600 |
C4—O4 | 1.427 (3) | C19—H19B | 0.9600 |
C4—C3 | 1.510 (3) | C19—H19C | 0.9600 |
C4—H4A | 0.9800 | C15—C16 | 1.536 (4) |
C2—C3 | 1.513 (3) | C15—H15A | 0.9700 |
C2—C1 | 1.517 (4) | C15—H15B | 0.9700 |
C2—H2A | 0.9700 | C18—H18A | 0.9600 |
C2—H2B | 0.9700 | C18—H18B | 0.9600 |
C13—C12 | 1.512 (3) | C18—H18C | 0.9600 |
C13—C17 | 1.519 (4) | C17—C16 | 1.517 (5) |
C13—C18 | 1.548 (3) | C16—H16A | 0.9700 |
O4—H4 | 0.83 (3) | C16—H16B | 0.9700 |
C7—C6 | 1.523 (3) | | |
| | | |
C6—C5—C4 | 111.39 (18) | C4—C3—C2 | 112.30 (17) |
C6—C5—C10 | 111.42 (16) | O3—C3—H3A | 108.6 |
C4—C5—C10 | 113.25 (16) | C4—C3—H3A | 108.6 |
C6—C5—H5 | 106.8 | C2—C3—H3A | 108.6 |
C4—C5—H5 | 106.8 | C12—C11—C9 | 113.5 (2) |
C10—C5—H5 | 106.8 | C12—C11—H11A | 108.9 |
C7—C8—C14 | 111.83 (17) | C9—C11—H11A | 108.9 |
C7—C8—C9 | 110.25 (15) | C12—C11—H11B | 108.9 |
C14—C8—C9 | 108.60 (16) | C9—C11—H11B | 108.9 |
C7—C8—H8 | 108.7 | H11A—C11—H11B | 107.7 |
C14—C8—H8 | 108.7 | C2—C1—C10 | 114.44 (18) |
C9—C8—H8 | 108.7 | C2—C1—H1A | 108.7 |
C1—C10—C19 | 106.86 (19) | C10—C1—H1A | 108.7 |
C1—C10—C5 | 107.99 (16) | C2—C1—H1B | 108.7 |
C19—C10—C5 | 109.32 (18) | C10—C1—H1B | 108.7 |
C1—C10—C9 | 111.90 (17) | H1A—C1—H1B | 107.6 |
C19—C10—C9 | 111.67 (17) | C3—O3—H3 | 105 (2) |
C5—C10—C9 | 109.01 (16) | C13—C12—C11 | 110.05 (19) |
C11—C9—C8 | 112.34 (15) | C13—C12—H12A | 109.7 |
C11—C9—C10 | 113.85 (18) | C11—C12—H12A | 109.7 |
C8—C9—C10 | 111.67 (16) | C13—C12—H12B | 109.7 |
C11—C9—H9 | 106.1 | C11—C12—H12B | 109.7 |
C8—C9—H9 | 106.1 | H12A—C12—H12B | 108.2 |
C10—C9—H9 | 106.1 | C7—C6—C5 | 112.74 (18) |
C8—C14—C13 | 113.58 (18) | C7—C6—H6A | 109.0 |
C8—C14—C15 | 120.12 (19) | C5—C6—H6A | 109.0 |
C13—C14—C15 | 104.35 (17) | C7—C6—H6B | 109.0 |
C8—C14—H14 | 105.9 | C5—C6—H6B | 109.0 |
C13—C14—H14 | 105.9 | H6A—C6—H6B | 107.8 |
C15—C14—H14 | 105.9 | C10—C19—H19A | 109.5 |
O4—C4—C3 | 108.64 (17) | C10—C19—H19B | 109.5 |
O4—C4—C5 | 108.61 (16) | H19A—C19—H19B | 109.5 |
C3—C4—C5 | 112.39 (18) | C10—C19—H19C | 109.5 |
O4—C4—H4A | 109.0 | H19A—C19—H19C | 109.5 |
C3—C4—H4A | 109.0 | H19B—C19—H19C | 109.5 |
C5—C4—H4A | 109.0 | C14—C15—C16 | 103.4 (2) |
C3—C2—C1 | 109.74 (19) | C14—C15—H15A | 111.1 |
C3—C2—H2A | 109.7 | C16—C15—H15A | 111.1 |
C1—C2—H2A | 109.7 | C14—C15—H15B | 111.1 |
C3—C2—H2B | 109.7 | C16—C15—H15B | 111.1 |
C1—C2—H2B | 109.7 | H15A—C15—H15B | 109.0 |
H2A—C2—H2B | 108.2 | C13—C18—H18A | 109.5 |
C12—C13—C17 | 116.8 (2) | C13—C18—H18B | 109.5 |
C12—C13—C14 | 109.86 (17) | H18A—C18—H18B | 109.5 |
C17—C13—C14 | 98.9 (2) | C13—C18—H18C | 109.5 |
C12—C13—C18 | 110.9 (2) | H18A—C18—H18C | 109.5 |
C17—C13—C18 | 105.85 (19) | H18B—C18—H18C | 109.5 |
C14—C13—C18 | 114.1 (2) | O17—C17—C16 | 125.9 (3) |
C4—O4—H4 | 110 (2) | O17—C17—C13 | 125.6 (3) |
C8—C7—C6 | 113.15 (18) | C16—C17—C13 | 108.5 (2) |
C8—C7—H7A | 108.9 | C17—C16—C15 | 105.0 (2) |
C6—C7—H7A | 108.9 | C17—C16—H16A | 110.8 |
C8—C7—H7B | 108.9 | C15—C16—H16A | 110.8 |
C6—C7—H7B | 108.9 | C17—C16—H16B | 110.8 |
H7A—C7—H7B | 107.8 | C15—C16—H16B | 110.8 |
O3—C3—C4 | 110.2 (2) | H16A—C16—H16B | 108.8 |
O3—C3—C2 | 108.48 (19) | | |
| | | |
C6—C5—C10—C1 | 177.43 (17) | O4—C4—C3—O3 | −65.2 (2) |
C4—C5—C10—C1 | 50.9 (2) | C5—C4—C3—O3 | 174.63 (16) |
C6—C5—C10—C19 | −66.7 (2) | O4—C4—C3—C2 | 173.81 (18) |
C4—C5—C10—C19 | 166.82 (18) | C5—C4—C3—C2 | 53.6 (2) |
C6—C5—C10—C9 | 55.6 (2) | C1—C2—C3—O3 | −177.32 (19) |
C4—C5—C10—C9 | −70.9 (2) | C1—C2—C3—C4 | −55.3 (2) |
C7—C8—C9—C11 | −174.0 (2) | C8—C9—C11—C12 | 52.0 (3) |
C14—C8—C9—C11 | −51.2 (2) | C10—C9—C11—C12 | −179.8 (2) |
C7—C8—C9—C10 | 56.7 (2) | C3—C2—C1—C10 | 57.7 (2) |
C14—C8—C9—C10 | 179.50 (16) | C19—C10—C1—C2 | −172.38 (19) |
C1—C10—C9—C11 | 54.2 (2) | C5—C10—C1—C2 | −54.9 (2) |
C19—C10—C9—C11 | −65.5 (2) | C9—C10—C1—C2 | 65.1 (2) |
C5—C10—C9—C11 | 173.58 (18) | C17—C13—C12—C11 | 167.9 (2) |
C1—C10—C9—C8 | −177.28 (16) | C14—C13—C12—C11 | 56.4 (3) |
C19—C10—C9—C8 | 63.0 (2) | C18—C13—C12—C11 | −70.7 (2) |
C5—C10—C9—C8 | −57.9 (2) | C9—C11—C12—C13 | −54.1 (3) |
C7—C8—C14—C13 | 178.24 (18) | C8—C7—C6—C5 | 52.5 (3) |
C9—C8—C14—C13 | 56.4 (2) | C4—C5—C6—C7 | 74.0 (2) |
C7—C8—C14—C15 | −57.3 (3) | C10—C5—C6—C7 | −53.6 (2) |
C9—C8—C14—C15 | −179.18 (18) | C8—C14—C15—C16 | −166.2 (2) |
C6—C5—C4—O4 | 61.1 (2) | C13—C14—C15—C16 | −37.5 (2) |
C10—C5—C4—O4 | −172.33 (16) | C12—C13—C17—O17 | 24.5 (4) |
C6—C5—C4—C3 | −178.63 (16) | C14—C13—C17—O17 | 142.2 (3) |
C10—C5—C4—C3 | −52.1 (2) | C18—C13—C17—O17 | −99.5 (3) |
C8—C14—C13—C12 | −60.3 (2) | C12—C13—C17—C16 | −153.1 (2) |
C15—C14—C13—C12 | 167.1 (2) | C14—C13—C17—C16 | −35.4 (2) |
C8—C14—C13—C17 | 176.87 (17) | C18—C13—C17—C16 | 82.9 (3) |
C15—C14—C13—C17 | 44.3 (2) | O17—C17—C16—C15 | −164.3 (2) |
C8—C14—C13—C18 | 65.0 (2) | C13—C17—C16—C15 | 13.4 (3) |
C15—C14—C13—C18 | −67.6 (2) | C14—C15—C16—C17 | 14.6 (3) |
C14—C8—C7—C6 | −174.20 (19) | C19—C10—C13—C18 | −2.8 (2) |
C9—C8—C7—C6 | −53.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3i | 0.83 (3) | 1.93 (3) | 2.751 (3) | 168 (3) |
O3—H3···O17ii | 0.84 (4) | 2.04 (4) | 2.792 (3) | 149 (4) |
Symmetry codes: (i) −x+2, y−1/2, −z; (ii) x, y, z−1. |