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The crystal structures of six synthetic 2-oxa-steroids (
A-ring lactone steroids) have been determined by single-crystal X-ray diffraction. The conformation and hydrogen bonding in these oxa-steroids is compared with packing motifs in the natural steroids and the anabolic agent, Anavar
®. O—H
O hydrogen bonding with lactone carbonyl O is the preferred arrangement in molecules with a C—OH group. The donor H atoms of
A,
B and
D rings participate in C—H
O interactions with lactone carbonyl O and
D-ring hydroxyl/ketone O acceptor atoms. The conformation of the lactone ring in these analogues is different from the natural androgens because replacement of the C2-methylene group by an O atom changes the geometry of the
A ring. Two structurally related lactone steroids provide the first example of O—H
O/C—H
O interaction mimicry and furthermore the two components form a binary solid solution. The O—H
O and C—H
O hydrogen bonds in 2-oxa-steroid crystal structures are analysed and the observed preferences discussed in terms of geometric and chemical factors.
Supporting information
CCDC references: 145825; 145826; 145827; 145828; 145829; 145830; 145831
Data collection: Kuma KM-4 for (10), (11), (12), (13), (14), (15); KUMA KM-4 for (22). Cell refinement: Kuma KM-4 for (10), (11), (12), (13), (14), (15); KUMA KM-4 for (22). Data reduction: Kuma KM-4 for (10), (11), (12), (13), (14), (15); KUMA KM-4 for (22). Program(s) used to solve structure: SHELX97 (Sheldrick, 1997) for (10), (22); SHELXS97 (Sheldrick, 1990) for (11), (12), (14); SHELXS86 (Sheldrick, 1990) for (13), (15). Program(s) used to refine structure: SHELX97 (Sheldrick, 1997) for (10), (22); SHELXL97 (Sheldrick, 1997) for (11), (12), (14); SHELXL93 (Sheldrick, 1993) for (13), (15). For all compounds, molecular graphics: ORTEP and PLUTO. Software used to prepare material for publication: SHELX97 for (10), (22); SHELXL93 for (11), (12), (13), (14), (15).
(10) 2-Oxa-4-androsten-3,17-dione
top
Crystal data top
C18H24O3 | F(000) = 312 |
Mr = 288.37 | Dx = 1.218 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2y1 | Cell parameters from 62 reflections |
a = 6.2321 (3) Å | θ = 19–51° |
b = 9.9264 (6) Å | µ = 0.65 mm−1 |
c = 12.8120 (8) Å | T = 293 K |
β = 97.079 (5)° | Cubic, colourless |
V = 786.54 (8) Å3 | 0.45 × 0.30 × 0.20 mm |
Z = 2 | |
Data collection top
KM-4 diffractometer | Rint = 0.014 |
Radiation source: fine-focus sealed tube | θmax = 70.1°, θmin = 3.5° |
Graphite monochromator | h = 0→7 |
ω–2θ scans | k = 0→12 |
1685 measured reflections | l = −15→15 |
1597 independent reflections | 2 standard reflections every 100 reflections |
1434 reflections with I > 2σ(I) | intensity decay: less than 2% |
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)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | Calculated w = 1/[σ2(Fo2) + (0.0527P)2 + 0.0545P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.011 |
1597 reflections | Δρmax = 0.10 e Å−3 |
190 parameters | Δρmin = −0.13 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (3) |
Crystal data top
C18H24O3 | V = 786.54 (8) Å3 |
Mr = 288.37 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 6.2321 (3) Å | µ = 0.65 mm−1 |
b = 9.9264 (6) Å | T = 293 K |
c = 12.8120 (8) Å | 0.45 × 0.30 × 0.20 mm |
β = 97.079 (5)° | |
Data collection top
KM-4 diffractometer | Rint = 0.014 |
1685 measured reflections | 2 standard reflections every 100 reflections |
1597 independent reflections | intensity decay: less than 2% |
1434 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | Δρmax = 0.10 e Å−3 |
S = 1.06 | Δρmin = −0.13 e Å−3 |
1597 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
190 parameters | Absolute structure parameter: 0.1 (3) |
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 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 | |
C1 | 1.1263 (4) | 0.2306 (2) | 0.22518 (19) | 0.0696 (6) | |
H11 | 1.0335 | 0.2052 | 0.1618 | 0.082* | |
H12 | 1.2515 | 0.2762 | 0.2039 | 0.096* | |
O2 | 1.1971 (3) | 0.11026 (19) | 0.28226 (16) | 0.0858 (5) | |
C3 | 1.3028 (4) | 0.1287 (3) | 0.3798 (2) | 0.0839 (8) | |
O3 | 1.3906 (4) | 0.0318 (3) | 0.4234 (2) | 0.1192 (9) | |
C4 | 1.2911 (4) | 0.2600 (3) | 0.42700 (19) | 0.0754 (7) | |
H4 | 1.3897 | 0.2809 | 0.4853 | 0.096* | |
C5 | 1.1458 (3) | 0.3527 (3) | 0.39113 (16) | 0.0624 (5) | |
C6 | 1.1056 (4) | 0.4757 (3) | 0.45224 (15) | 0.0747 (7) | |
H61 | 1.2257 | 0.4889 | 0.5070 | 0.094* | |
H62 | 0.9762 | 0.4624 | 0.4860 | 0.077* | |
C7 | 1.0780 (4) | 0.6012 (3) | 0.38444 (15) | 0.0686 (6) | |
H71 | 1.2151 | 0.6241 | 0.3605 | 0.089* | |
H72 | 1.0351 | 0.6759 | 0.4261 | 0.109* | |
C8 | 0.9081 (3) | 0.5802 (2) | 0.28952 (13) | 0.0523 (4) | |
H8 | 0.7689 | 0.5599 | 0.3142 | 0.064* | |
C9 | 0.9741 (3) | 0.4610 (2) | 0.22410 (13) | 0.0486 (4) | |
H9 | 1.1171 | 0.4839 | 0.2049 | 0.052* | |
C10 | 1.0048 (3) | 0.3277 (2) | 0.28776 (15) | 0.0563 (5) | |
C11 | 0.8260 (4) | 0.4432 (2) | 0.11926 (16) | 0.0616 (5) | |
H111 | 0.8866 | 0.3744 | 0.0778 | 0.098* | |
H112 | 0.6851 | 0.4123 | 0.1339 | 0.063* | |
C12 | 0.7983 (4) | 0.5734 (2) | 0.05511 (14) | 0.0603 (5) | |
H121 | 0.9353 | 0.5984 | 0.0319 | 0.069* | |
H122 | 0.6943 | 0.5592 | −0.0067 | 0.085* | |
C13 | 0.7212 (3) | 0.6853 (2) | 0.12066 (15) | 0.0527 (5) | |
C14 | 0.8830 (3) | 0.7043 (2) | 0.21968 (14) | 0.0531 (4) | |
H14 | 1.0239 | 0.7179 | 0.1948 | 0.062* | |
C15 | 0.8219 (5) | 0.8404 (3) | 0.26368 (19) | 0.0817 (7) | |
H151 | 0.9420 | 0.8791 | 0.3092 | 0.091* | |
H152 | 0.6984 | 0.8320 | 0.3025 | 0.073* | |
C16 | 0.7662 (6) | 0.9251 (3) | 0.1642 (2) | 0.0938 (9) | |
H161 | 0.6415 | 0.9817 | 0.1705 | 0.169* | |
H162 | 0.8872 | 0.9823 | 0.1524 | 0.122* | |
C17 | 0.7175 (3) | 0.8266 (2) | 0.07520 (17) | 0.0637 (5) | |
O17 | 0.6860 (3) | 0.8564 (2) | −0.01645 (13) | 0.0850 (5) | |
C18 | 0.4875 (3) | 0.6608 (3) | 0.1442 (2) | 0.0760 (7) | |
H181 | 0.4822 | 0.5797 | 0.1847 | 0.102* | |
H182 | 0.3937 | 0.6520 | 0.0793 | 0.099* | |
H183 | 0.4410 | 0.7356 | 0.1834 | 0.092* | |
C19 | 0.7893 (3) | 0.2667 (3) | 0.3118 (2) | 0.0752 (6) | |
H191 | 0.8165 | 0.1831 | 0.3487 | 0.080* | |
H192 | 0.6977 | 0.2508 | 0.2471 | 0.104* | |
H193 | 0.7193 | 0.3282 | 0.3545 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0730 (13) | 0.0606 (14) | 0.0757 (13) | 0.0066 (11) | 0.0110 (10) | 0.0072 (11) |
O2 | 0.0834 (11) | 0.0667 (11) | 0.1062 (13) | 0.0127 (9) | 0.0075 (10) | 0.0180 (10) |
C3 | 0.0568 (12) | 0.095 (2) | 0.1014 (19) | 0.0119 (13) | 0.0153 (12) | 0.0369 (17) |
O3 | 0.0904 (14) | 0.1103 (18) | 0.155 (2) | 0.0298 (13) | 0.0053 (14) | 0.0537 (17) |
C4 | 0.0576 (11) | 0.0976 (19) | 0.0712 (14) | 0.0064 (12) | 0.0090 (10) | 0.0258 (14) |
C5 | 0.0543 (10) | 0.0811 (15) | 0.0530 (10) | −0.0029 (11) | 0.0116 (8) | 0.0166 (11) |
C6 | 0.0819 (14) | 0.100 (2) | 0.0411 (9) | 0.0057 (14) | 0.0020 (9) | 0.0047 (11) |
C7 | 0.0782 (14) | 0.0805 (15) | 0.0448 (10) | −0.0049 (13) | −0.0012 (9) | −0.0077 (11) |
C8 | 0.0553 (10) | 0.0615 (12) | 0.0408 (8) | −0.0068 (8) | 0.0083 (7) | −0.0014 (8) |
C9 | 0.0465 (8) | 0.0562 (11) | 0.0433 (8) | −0.0067 (8) | 0.0062 (7) | 0.0018 (8) |
C10 | 0.0502 (9) | 0.0601 (12) | 0.0595 (11) | −0.0037 (9) | 0.0103 (8) | 0.0103 (10) |
C11 | 0.0697 (12) | 0.0580 (12) | 0.0535 (10) | −0.0012 (10) | −0.0064 (9) | −0.0089 (9) |
C12 | 0.0679 (12) | 0.0682 (13) | 0.0423 (8) | 0.0057 (10) | −0.0037 (8) | −0.0058 (9) |
C13 | 0.0517 (10) | 0.0570 (12) | 0.0492 (9) | −0.0029 (8) | 0.0051 (8) | −0.0006 (8) |
C14 | 0.0583 (9) | 0.0553 (10) | 0.0456 (9) | −0.0075 (9) | 0.0066 (7) | −0.0039 (8) |
C15 | 0.114 (2) | 0.0639 (14) | 0.0647 (14) | 0.0024 (15) | −0.0001 (13) | −0.0144 (12) |
C16 | 0.134 (3) | 0.0586 (15) | 0.0852 (18) | −0.0001 (16) | −0.0031 (17) | −0.0017 (13) |
C17 | 0.0624 (11) | 0.0655 (13) | 0.0630 (13) | 0.0036 (10) | 0.0065 (9) | 0.0064 (11) |
O17 | 0.1050 (12) | 0.0829 (12) | 0.0662 (9) | 0.0225 (11) | 0.0070 (8) | 0.0178 (9) |
C18 | 0.0518 (10) | 0.0865 (17) | 0.0903 (15) | −0.0026 (11) | 0.0115 (10) | 0.0031 (14) |
C19 | 0.0569 (11) | 0.0755 (14) | 0.0938 (16) | −0.0102 (11) | 0.0120 (10) | 0.0222 (14) |
Geometric parameters (Å, º) top
C1—O2 | 1.441 (3) | C11—C12 | 1.530 (3) |
C1—C10 | 1.515 (3) | C11—H111 | 0.9700 |
C1—H11 | 0.9700 | C11—H112 | 0.9700 |
C1—H12 | 0.9700 | C12—C13 | 1.506 (3) |
O2—C3 | 1.351 (3) | C12—H121 | 0.9700 |
C3—O3 | 1.209 (3) | C12—H122 | 0.9700 |
C3—C4 | 1.442 (4) | C13—C17 | 1.518 (3) |
C4—C5 | 1.333 (4) | C13—C14 | 1.532 (2) |
C4—H4 | 0.9300 | C13—C18 | 1.543 (3) |
C5—C6 | 1.488 (4) | C14—C15 | 1.530 (3) |
C5—C10 | 1.517 (3) | C14—H14 | 0.9800 |
C6—C7 | 1.516 (4) | C15—C16 | 1.531 (4) |
C6—H61 | 0.9700 | C15—H151 | 0.9700 |
C6—H62 | 0.9700 | C15—H152 | 0.9700 |
C7—C8 | 1.525 (3) | C16—C17 | 1.504 (4) |
C7—H71 | 0.9700 | C16—H161 | 0.9700 |
C7—H72 | 0.9700 | C16—H162 | 0.9700 |
C8—C14 | 1.520 (3) | C17—O17 | 1.203 (3) |
C8—C9 | 1.535 (3) | C18—H181 | 0.9600 |
C8—H8 | 0.9800 | C18—H182 | 0.9600 |
C9—C11 | 1.543 (2) | C18—H183 | 0.9600 |
C9—C10 | 1.554 (3) | C19—H191 | 0.9600 |
C9—H9 | 0.9800 | C19—H192 | 0.9600 |
C10—C19 | 1.538 (3) | C19—H193 | 0.9600 |
| | | |
O2—C1—C10 | 113.61 (18) | C12—C11—H112 | 109.0 |
O2—C1—H11 | 108.8 | C9—C11—H112 | 109.0 |
C10—C1—H11 | 108.8 | H111—C11—H112 | 107.8 |
O2—C1—H12 | 108.8 | C13—C12—C11 | 110.23 (16) |
C10—C1—H12 | 108.8 | C13—C12—H121 | 109.6 |
H11—C1—H12 | 107.7 | C11—C12—H121 | 109.6 |
C3—O2—C1 | 116.2 (2) | C13—C12—H122 | 109.6 |
O3—C3—O2 | 117.5 (3) | C11—C12—H122 | 109.6 |
O3—C3—C4 | 124.6 (3) | H121—C12—H122 | 108.1 |
O2—C3—C4 | 117.8 (2) | C12—C13—C17 | 117.27 (17) |
C5—C4—C3 | 123.1 (2) | C12—C13—C14 | 109.27 (17) |
C5—C4—H4 | 118.4 | C17—C13—C14 | 100.43 (17) |
C3—C4—H4 | 118.4 | C12—C13—C18 | 111.52 (19) |
C4—C5—C6 | 122.5 (2) | C17—C13—C18 | 104.50 (19) |
C4—C5—C10 | 119.0 (2) | C14—C13—C18 | 113.48 (17) |
C6—C5—C10 | 118.45 (19) | C8—C14—C15 | 120.75 (16) |
C5—C6—C7 | 112.79 (16) | C8—C14—C13 | 113.39 (17) |
C5—C6—H61 | 109.0 | C15—C14—C13 | 104.22 (18) |
C7—C6—H61 | 109.0 | C8—C14—H14 | 105.8 |
C5—C6—H62 | 109.0 | C15—C14—H14 | 105.8 |
C7—C6—H62 | 109.0 | C13—C14—H14 | 105.8 |
H61—C6—H62 | 107.8 | C14—C15—C16 | 102.67 (19) |
C6—C7—C8 | 111.3 (2) | C14—C15—H151 | 111.2 |
C6—C7—H71 | 109.4 | C16—C15—H151 | 111.2 |
C8—C7—H71 | 109.4 | C14—C15—H152 | 111.2 |
C6—C7—H72 | 109.4 | C16—C15—H152 | 111.2 |
C8—C7—H72 | 109.4 | H151—C15—H152 | 109.1 |
H71—C7—H72 | 108.0 | C17—C16—C15 | 106.1 (2) |
C14—C8—C7 | 111.67 (18) | C17—C16—H161 | 110.5 |
C14—C8—C9 | 108.57 (14) | C15—C16—H161 | 110.5 |
C7—C8—C9 | 109.55 (18) | C17—C16—H162 | 110.5 |
C14—C8—H8 | 109.0 | C15—C16—H162 | 110.5 |
C7—C8—H8 | 109.0 | H161—C16—H162 | 108.7 |
C9—C8—H8 | 109.0 | O17—C17—C16 | 125.0 (2) |
C8—C9—C11 | 113.07 (16) | O17—C17—C13 | 126.5 (2) |
C8—C9—C10 | 113.18 (14) | C16—C17—C13 | 108.53 (18) |
C11—C9—C10 | 112.40 (16) | C13—C18—H181 | 109.5 |
C8—C9—H9 | 105.8 | C13—C18—H182 | 109.5 |
C11—C9—H9 | 105.8 | H181—C18—H182 | 109.5 |
C10—C9—H9 | 105.8 | C13—C18—H183 | 109.5 |
C1—C10—C5 | 107.02 (17) | H181—C18—H183 | 109.5 |
C1—C10—C19 | 111.2 (2) | H182—C18—H183 | 109.5 |
C5—C10—C19 | 108.43 (16) | C10—C19—H191 | 109.5 |
C1—C10—C9 | 107.54 (15) | C10—C19—H192 | 109.5 |
C5—C10—C9 | 109.84 (17) | H191—C19—H192 | 109.5 |
C19—C10—C9 | 112.70 (17) | C10—C19—H193 | 109.5 |
C12—C11—C9 | 112.75 (17) | H191—C19—H193 | 109.5 |
C12—C11—H111 | 109.0 | H192—C19—H193 | 109.5 |
C9—C11—H111 | 109.0 | | |
(11) 2-Oxa-5-alpha-androstane-3,17-dione
top
Crystal data top
C18H26O3 | Dx = 1.219 Mg m−3 |
Mr = 290.39 | Melting point = 160–162 K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 91 reflections |
a = 6.3180 (4) Å | θ = 14–51° |
b = 6.4489 (5) Å | µ = 0.64 mm−1 |
c = 38.841 (3) Å | T = 293 K |
V = 1582.5 (2) Å3 | Prism, colourless |
Z = 4 | 0.45 × 0.40 × 0.10 mm |
F(000) = 632 | |
Data collection top
KM-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 70.2°, θmin = 4.6° |
Graphite monochromator | h = −7→7 |
ω–2θ scans | k = −7→7 |
1736 measured reflections | l = −47→44 |
1736 independent reflections | 2 standard reflections every 100 reflections |
1567 reflections with I > 2σ(I) | intensity decay: less than 2% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0488P)2 + 0.243P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.089 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.16 e Å−3 |
1736 reflections | Δρmin = −0.11 e Å−3 |
219 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0047 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.2 (3) |
Crystal data top
C18H26O3 | V = 1582.5 (2) Å3 |
Mr = 290.39 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 6.3180 (4) Å | µ = 0.64 mm−1 |
b = 6.4489 (5) Å | T = 293 K |
c = 38.841 (3) Å | 0.45 × 0.40 × 0.10 mm |
Data collection top
KM-4 diffractometer | Rint = 0.000 |
1736 measured reflections | 2 standard reflections every 100 reflections |
1736 independent reflections | intensity decay: less than 2% |
1567 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | Δρmax = 0.16 e Å−3 |
S = 1.05 | Δρmin = −0.11 e Å−3 |
1736 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
219 parameters | Absolute structure parameter: −0.2 (3) |
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 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 | |
C1 | −0.0582 (3) | 0.9326 (3) | 0.79506 (4) | 0.0419 (4) | |
H11 | −0.1541 | 0.8198 | 0.8006 | 0.049 (6)* | |
H12 | −0.1372 | 1.0612 | 0.7966 | 0.044 (6)* | |
O2 | 0.0174 (2) | 0.9068 (2) | 0.76001 (3) | 0.0481 (4) | |
C3 | 0.2001 (3) | 0.9911 (3) | 0.74977 (5) | 0.0434 (5) | |
O3 | 0.2510 (3) | 0.9691 (2) | 0.72007 (3) | 0.0592 (4) | |
C4 | 0.3376 (3) | 1.1024 (3) | 0.77508 (4) | 0.0451 (5) | |
H41 | 0.3670 | 1.2396 | 0.7660 | 0.064 (7)* | |
H42 | 0.4715 | 1.0293 | 0.7765 | 0.059 (7)* | |
C5 | 0.2509 (3) | 1.1270 (3) | 0.81162 (4) | 0.0352 (4) | |
H51 | 0.1533 | 1.2451 | 0.8112 | 0.042 (6)* | |
C6 | 0.4217 (3) | 1.1785 (3) | 0.83763 (4) | 0.0442 (5) | |
H61 | 0.4944 | 1.3042 | 0.8307 | 0.054 (6)* | |
H62 | 0.5246 | 1.0670 | 0.8384 | 0.056 (6)* | |
C7 | 0.3253 (3) | 1.2087 (3) | 0.87310 (5) | 0.0450 (5) | |
H71 | 0.2349 | 1.3302 | 0.8728 | 0.050 (6)* | |
H72 | 0.4376 | 1.2331 | 0.8897 | 0.061 (6)* | |
C8 | 0.1962 (3) | 1.0214 (3) | 0.88445 (4) | 0.0361 (4) | |
H81 | 0.2915 | 0.9021 | 0.8864 | 0.046 (5)* | |
C9 | 0.0231 (3) | 0.9695 (3) | 0.85760 (4) | 0.0340 (4) | |
H91 | −0.0666 | 1.0930 | 0.8559 | 0.034 (5)* | |
C10 | 0.1199 (3) | 0.9361 (3) | 0.82138 (4) | 0.0338 (4) | |
C11 | −0.1218 (3) | 0.7931 (3) | 0.86941 (5) | 0.0462 (5) | |
H111 | −0.0416 | 0.6649 | 0.8696 | 0.042 (5)* | |
H112 | −0.2358 | 0.7775 | 0.8529 | 0.069 (7)* | |
C12 | −0.2171 (4) | 0.8281 (4) | 0.90522 (5) | 0.0563 (6) | |
H121 | −0.3133 | 0.9452 | 0.9046 | 0.072 (8)* | |
H122 | −0.2967 | 0.7064 | 0.9122 | 0.081 (9)* | |
C13 | −0.0421 (4) | 0.8694 (3) | 0.93091 (5) | 0.0482 (5) | |
C14 | 0.0900 (3) | 1.0552 (3) | 0.91907 (4) | 0.0415 (5) | |
H141 | −0.0102 | 1.1695 | 0.9157 | 0.040 (5)* | |
C15 | 0.2217 (4) | 1.1123 (4) | 0.95089 (5) | 0.0565 (6) | |
H151 | 0.2702 | 1.2548 | 0.9498 | 0.070 (7)* | |
H152 | 0.3430 | 1.0213 | 0.9533 | 0.064 (7)* | |
C16 | 0.0632 (5) | 1.0812 (4) | 0.98048 (5) | 0.0692 (7) | |
H161 | 0.1313 | 1.0147 | 0.9999 | 0.087 (9)* | |
H162 | 0.0062 | 1.2134 | 0.9880 | 0.102 (11)* | |
C17 | −0.1103 (4) | 0.9451 (4) | 0.96620 (5) | 0.0620 (7) | |
O17 | −0.2762 (3) | 0.9051 (4) | 0.98011 (4) | 0.0924 (7) | |
C18 | 0.2467 (4) | 0.7335 (3) | 0.81936 (5) | 0.0482 (5) | |
H181 | 0.3180 | 0.7259 | 0.7976 | 0.071 (8)* | |
H182 | 0.1523 | 0.6177 | 0.8216 | 0.076 (8)* | |
H183 | 0.3491 | 0.7301 | 0.8376 | 0.089 (10)* | |
C19 | 0.0895 (5) | 0.6716 (4) | 0.93745 (6) | 0.0620 (7) | |
H191 | 0.1647 | 0.6348 | 0.9169 | 0.083 (9)* | |
H192 | −0.0031 | 0.5601 | 0.9439 | 0.120 (13)* | |
H193 | 0.1888 | 0.6968 | 0.9557 | 0.097 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0450 (10) | 0.0502 (10) | 0.0304 (9) | −0.0044 (10) | −0.0018 (8) | −0.0018 (8) |
O2 | 0.0584 (8) | 0.0559 (8) | 0.0300 (7) | −0.0073 (8) | −0.0012 (6) | −0.0041 (6) |
C3 | 0.0540 (11) | 0.0420 (10) | 0.0343 (10) | 0.0099 (9) | 0.0010 (8) | 0.0027 (7) |
O3 | 0.0779 (10) | 0.0664 (9) | 0.0332 (7) | 0.0125 (9) | 0.0114 (7) | −0.0028 (6) |
C4 | 0.0453 (10) | 0.0535 (11) | 0.0365 (9) | −0.0023 (10) | 0.0061 (8) | 0.0037 (9) |
C5 | 0.0365 (9) | 0.0348 (9) | 0.0341 (9) | 0.0017 (8) | 0.0010 (8) | 0.0011 (7) |
C6 | 0.0414 (10) | 0.0498 (11) | 0.0413 (10) | −0.0075 (10) | 0.0001 (8) | −0.0006 (9) |
C7 | 0.0491 (11) | 0.0467 (10) | 0.0391 (10) | −0.0054 (10) | −0.0046 (9) | −0.0042 (8) |
C8 | 0.0401 (9) | 0.0373 (9) | 0.0310 (9) | 0.0044 (8) | −0.0030 (7) | −0.0004 (7) |
C9 | 0.0364 (9) | 0.0349 (8) | 0.0307 (8) | 0.0035 (8) | 0.0002 (7) | 0.0025 (7) |
C10 | 0.0386 (9) | 0.0325 (8) | 0.0302 (9) | 0.0028 (8) | −0.0003 (7) | −0.0007 (7) |
C11 | 0.0482 (11) | 0.0533 (12) | 0.0370 (10) | −0.0108 (10) | −0.0006 (8) | 0.0064 (9) |
C12 | 0.0550 (12) | 0.0701 (15) | 0.0439 (11) | −0.0092 (13) | 0.0097 (10) | 0.0108 (10) |
C13 | 0.0596 (12) | 0.0517 (11) | 0.0335 (10) | 0.0085 (11) | 0.0049 (9) | 0.0077 (8) |
C14 | 0.0515 (11) | 0.0423 (10) | 0.0305 (9) | 0.0108 (10) | −0.0015 (8) | 0.0003 (7) |
C15 | 0.0735 (14) | 0.0613 (13) | 0.0347 (10) | 0.0085 (13) | −0.0089 (10) | −0.0064 (9) |
C16 | 0.1018 (19) | 0.0726 (15) | 0.0332 (11) | 0.0162 (17) | 0.0051 (12) | −0.0040 (11) |
C17 | 0.0812 (16) | 0.0685 (15) | 0.0364 (11) | 0.0185 (14) | 0.0123 (11) | 0.0118 (11) |
O17 | 0.0992 (14) | 0.1262 (17) | 0.0519 (10) | 0.0060 (16) | 0.0323 (10) | 0.0120 (11) |
C18 | 0.0624 (13) | 0.0364 (9) | 0.0459 (11) | 0.0109 (10) | 0.0055 (10) | 0.0009 (8) |
C19 | 0.0915 (18) | 0.0492 (12) | 0.0453 (12) | 0.0135 (14) | 0.0004 (12) | 0.0102 (10) |
Geometric parameters (Å, º) top
C1—O2 | 1.452 (2) | C10—C18 | 1.535 (2) |
C1—C10 | 1.520 (2) | C11—C12 | 1.532 (3) |
C1—H11 | 0.9700 | C11—H111 | 0.9700 |
C1—H12 | 0.9700 | C11—H112 | 0.9700 |
O2—C3 | 1.337 (3) | C12—C13 | 1.513 (3) |
C3—O3 | 1.206 (2) | C12—H121 | 0.9700 |
C3—C4 | 1.496 (3) | C12—H122 | 0.9700 |
C4—C5 | 1.529 (2) | C13—C17 | 1.518 (3) |
C4—H41 | 0.9700 | C13—C14 | 1.531 (3) |
C4—H42 | 0.9700 | C13—C19 | 1.544 (3) |
C5—C6 | 1.515 (2) | C14—C15 | 1.535 (3) |
C5—C10 | 1.531 (2) | C14—H141 | 0.9800 |
C5—H51 | 0.9800 | C15—C16 | 1.538 (3) |
C6—C7 | 1.519 (3) | C15—H151 | 0.9700 |
C6—H61 | 0.9700 | C15—H152 | 0.9700 |
C6—H62 | 0.9700 | C16—C17 | 1.510 (4) |
C7—C8 | 1.523 (3) | C16—H161 | 0.9700 |
C7—H71 | 0.9700 | C16—H162 | 0.9700 |
C7—H72 | 0.9700 | C17—O17 | 1.207 (3) |
C8—C14 | 1.519 (2) | C18—H181 | 0.9600 |
C8—C9 | 1.548 (2) | C18—H182 | 0.9600 |
C8—H81 | 0.9800 | C18—H183 | 0.9600 |
C9—C11 | 1.530 (3) | C19—H191 | 0.9600 |
C9—C10 | 1.549 (2) | C19—H192 | 0.9600 |
C9—H91 | 0.9800 | C19—H193 | 0.9600 |
| | | |
O2—C1—C10 | 112.88 (16) | C9—C11—C12 | 113.45 (17) |
O2—C1—H11 | 109.0 | C9—C11—H111 | 108.9 |
C10—C1—H11 | 109.0 | C12—C11—H111 | 108.9 |
O2—C1—H12 | 109.0 | C9—C11—H112 | 108.9 |
C10—C1—H12 | 109.0 | C12—C11—H112 | 108.9 |
H11—C1—H12 | 107.8 | H111—C11—H112 | 107.7 |
C3—O2—C1 | 121.09 (15) | C13—C12—C11 | 109.70 (18) |
O3—C3—O2 | 117.83 (19) | C13—C12—H121 | 109.7 |
O3—C3—C4 | 122.0 (2) | C11—C12—H121 | 109.7 |
O2—C3—C4 | 120.09 (16) | C13—C12—H122 | 109.7 |
C3—C4—C5 | 116.85 (16) | C11—C12—H122 | 109.7 |
C3—C4—H41 | 108.1 | H121—C12—H122 | 108.2 |
C5—C4—H41 | 108.1 | C12—C13—C17 | 116.40 (19) |
C3—C4—H42 | 108.1 | C12—C13—C14 | 109.76 (16) |
C5—C4—H42 | 108.1 | C17—C13—C14 | 100.03 (18) |
H41—C4—H42 | 107.3 | C12—C13—C19 | 110.9 (2) |
C6—C5—C4 | 112.72 (15) | C17—C13—C19 | 105.69 (17) |
C6—C5—C10 | 113.33 (14) | C14—C13—C19 | 113.75 (19) |
C4—C5—C10 | 109.88 (14) | C8—C14—C13 | 113.22 (16) |
C6—C5—H51 | 106.8 | C8—C14—C15 | 120.54 (17) |
C4—C5—H51 | 106.8 | C13—C14—C15 | 103.96 (16) |
C10—C5—H51 | 106.8 | C8—C14—H141 | 106.0 |
C5—C6—C7 | 110.33 (16) | C13—C14—H141 | 106.0 |
C5—C6—H61 | 109.6 | C15—C14—H141 | 106.0 |
C7—C6—H61 | 109.6 | C14—C15—C16 | 102.58 (19) |
C5—C6—H62 | 109.6 | C14—C15—H151 | 111.3 |
C7—C6—H62 | 109.6 | C16—C15—H151 | 111.3 |
H61—C6—H62 | 108.1 | C14—C15—H152 | 111.3 |
C6—C7—C8 | 112.08 (16) | C16—C15—H152 | 111.3 |
C6—C7—H71 | 109.2 | H151—C15—H152 | 109.2 |
C8—C7—H71 | 109.2 | C17—C16—C15 | 105.90 (17) |
C6—C7—H72 | 109.2 | C17—C16—H161 | 110.6 |
C8—C7—H72 | 109.2 | C15—C16—H161 | 110.6 |
H71—C7—H72 | 107.9 | C17—C16—H162 | 110.6 |
C14—C8—C7 | 112.27 (15) | C15—C16—H162 | 110.6 |
C14—C8—C9 | 108.40 (15) | H161—C16—H162 | 108.7 |
C7—C8—C9 | 110.81 (14) | O17—C17—C16 | 126.2 (2) |
C14—C8—H81 | 108.4 | O17—C17—C13 | 125.6 (3) |
C7—C8—H81 | 108.4 | C16—C17—C13 | 108.2 (2) |
C9—C8—H81 | 108.4 | C10—C18—H181 | 109.5 |
C11—C9—C8 | 112.44 (14) | C10—C18—H182 | 109.5 |
C11—C9—C10 | 113.90 (15) | H181—C18—H182 | 109.5 |
C8—C9—C10 | 111.29 (14) | C10—C18—H183 | 109.5 |
C11—C9—H91 | 106.2 | H181—C18—H183 | 109.5 |
C8—C9—H91 | 106.2 | H182—C18—H183 | 109.5 |
C10—C9—H91 | 106.2 | C13—C19—H191 | 109.5 |
C1—C10—C5 | 104.21 (14) | C13—C19—H192 | 109.5 |
C1—C10—C18 | 109.82 (16) | H191—C19—H192 | 109.5 |
C5—C10—C18 | 112.94 (15) | C13—C19—H193 | 109.5 |
C1—C10—C9 | 108.70 (14) | H191—C19—H193 | 109.5 |
C5—C10—C9 | 109.07 (13) | H192—C19—H193 | 109.5 |
C18—C10—C9 | 111.76 (14) | | |
(12) 17-Hydroxy-2-oxaandrost-4-ene-3-one
top
Crystal data top
C18H26O3 | Dx = 1.232 Mg m−3 |
Mr = 290.39 | Melting point = 200–202 K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 41 reflections |
a = 14.241 (2) Å | θ = 18–63° |
b = 9.4401 (9) Å | µ = 0.65 mm−1 |
c = 11.648 (2) Å | T = 293 K |
V = 1565.9 (4) Å3 | Prism, colourless |
Z = 4 | 0.70 × 0.70 × 0.25 mm |
F(000) = 632 | |
Data collection top
KM-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 70.1°, θmin = 4.9° |
Graphite monochromator | h = 0→17 |
ω–2θ scans | k = 0→11 |
1722 measured reflections | l = 0→14 |
1722 independent reflections | 2 standard reflections every 100 reflections |
1592 reflections with I > 2σ(I) | intensity decay: less than 2.7 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0602P)2 + 0.1629P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.096 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.17 e Å−3 |
1722 reflections | Δρmin = −0.10 e Å−3 |
222 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0078 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.2 (3) |
Crystal data top
C18H26O3 | V = 1565.9 (4) Å3 |
Mr = 290.39 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 14.241 (2) Å | µ = 0.65 mm−1 |
b = 9.4401 (9) Å | T = 293 K |
c = 11.648 (2) Å | 0.70 × 0.70 × 0.25 mm |
Data collection top
KM-4 diffractometer | Rint = 0.000 |
1722 measured reflections | 2 standard reflections every 100 reflections |
1722 independent reflections | intensity decay: less than 2.7 |
1592 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | Δρmax = 0.17 e Å−3 |
S = 1.07 | Δρmin = −0.10 e Å−3 |
1722 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
222 parameters | Absolute structure parameter: −0.2 (3) |
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 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 | |
C1 | 0.11952 (16) | −0.3651 (2) | 0.4163 (2) | 0.0589 (6) | |
H11 | 0.1084 | −0.3944 | 0.4950 | 0.090 (9)* | |
H12 | 0.0600 | −0.3695 | 0.3760 | 0.053 (6)* | |
O2 | 0.18402 (12) | −0.46399 (14) | 0.36346 (15) | 0.0642 (4) | |
C3 | 0.21884 (15) | −0.4286 (2) | 0.2612 (2) | 0.0567 (5) | |
O3 | 0.25854 (15) | −0.5203 (2) | 0.20574 (16) | 0.0787 (5) | |
C4 | 0.21500 (15) | −0.2819 (2) | 0.22666 (17) | 0.0536 (5) | |
H4 | 0.2292 | −0.2588 | 0.1510 | 0.079 (8)* | |
C5 | 0.19175 (13) | −0.1782 (2) | 0.29920 (16) | 0.0439 (4) | |
C6 | 0.20792 (16) | −0.0256 (2) | 0.2710 (2) | 0.0569 (5) | |
H61 | 0.2197 | −0.0167 | 0.1893 | 0.077 (8)* | |
H62 | 0.2635 | 0.0070 | 0.3112 | 0.080 (8)* | |
C7 | 0.12539 (16) | 0.0687 (2) | 0.30335 (19) | 0.0577 (5) | |
H71 | 0.0735 | 0.0503 | 0.2516 | 0.069 (7)* | |
H72 | 0.1434 | 0.1672 | 0.2944 | 0.074 (7)* | |
C8 | 0.09342 (13) | 0.04366 (17) | 0.42640 (16) | 0.0414 (4) | |
H8 | 0.1450 | 0.0675 | 0.4786 | 0.056 (6)* | |
C9 | 0.06817 (12) | −0.11419 (18) | 0.44190 (15) | 0.0395 (4) | |
H9 | 0.0215 | −0.1355 | 0.3826 | 0.055 (6)* | |
C10 | 0.15385 (13) | −0.21237 (17) | 0.41638 (15) | 0.0406 (4) | |
C11 | 0.02079 (17) | −0.1477 (2) | 0.55675 (19) | 0.0554 (5) | |
H111 | −0.0029 | −0.2440 | 0.5547 | 0.065 (7)* | |
H112 | 0.0673 | −0.1423 | 0.6174 | 0.074 (8)* | |
C12 | −0.06016 (14) | −0.0471 (2) | 0.58509 (19) | 0.0532 (5) | |
H121 | −0.1112 | −0.0626 | 0.5314 | 0.075 (8)* | |
H122 | −0.0833 | −0.0673 | 0.6617 | 0.065 (7)* | |
C13 | −0.02915 (13) | 0.10649 (18) | 0.57877 (16) | 0.0428 (4) | |
C14 | 0.00826 (13) | 0.13264 (18) | 0.45747 (16) | 0.0444 (4) | |
H14 | −0.0419 | 0.1044 | 0.4046 | 0.053 (6)* | |
C15 | 0.01574 (18) | 0.2947 (2) | 0.4492 (2) | 0.0666 (6) | |
H151 | 0.0082 | 0.3265 | 0.3705 | 0.101 (10)* | |
H152 | 0.0758 | 0.3278 | 0.4781 | 0.098 (10)* | |
C16 | −0.06548 (18) | 0.3475 (2) | 0.5251 (2) | 0.0695 (7) | |
H161 | −0.0422 | 0.4120 | 0.5833 | 0.080 (9)* | |
H162 | −0.1119 | 0.3967 | 0.4790 | 0.080 (8)* | |
C17 | −0.10878 (14) | 0.2162 (2) | 0.58098 (19) | 0.0536 (5) | |
H171 | −0.1603 | 0.1822 | 0.5324 | 0.062 (6)* | |
O17 | −0.14533 (12) | 0.25201 (18) | 0.69021 (15) | 0.0662 (4) | |
H17 | −0.182 (2) | 0.178 (3) | 0.716 (3) | 0.082 (9)* | |
C18 | 0.23351 (15) | −0.1962 (2) | 0.50425 (18) | 0.0557 (5) | |
H181 | 0.2099 | −0.2158 | 0.5798 | 0.092 (9)* | |
H182 | 0.2574 | −0.1011 | 0.5017 | 0.081 (8)* | |
H183 | 0.2830 | −0.2615 | 0.4862 | 0.084 (8)* | |
C19 | 0.04137 (16) | 0.1407 (3) | 0.67298 (19) | 0.0659 (6) | |
H191 | 0.0614 | 0.2374 | 0.6657 | 0.097 (10)* | |
H192 | 0.0947 | 0.0792 | 0.6661 | 0.088 (9)* | |
H193 | 0.0125 | 0.1271 | 0.7466 | 0.086 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0628 (12) | 0.0356 (9) | 0.0783 (14) | −0.0029 (9) | 0.0173 (11) | −0.0079 (9) |
O2 | 0.0727 (9) | 0.0387 (7) | 0.0812 (11) | 0.0029 (7) | 0.0126 (9) | −0.0108 (7) |
C3 | 0.0528 (11) | 0.0573 (11) | 0.0600 (12) | 0.0011 (10) | −0.0076 (10) | −0.0222 (10) |
O3 | 0.0894 (11) | 0.0731 (10) | 0.0735 (10) | 0.0243 (9) | −0.0054 (9) | −0.0337 (9) |
C4 | 0.0518 (10) | 0.0641 (12) | 0.0450 (10) | 0.0024 (9) | −0.0024 (8) | −0.0106 (9) |
C5 | 0.0403 (8) | 0.0460 (9) | 0.0455 (9) | −0.0038 (7) | −0.0008 (7) | −0.0034 (8) |
C6 | 0.0621 (12) | 0.0504 (11) | 0.0582 (12) | −0.0044 (9) | 0.0164 (10) | 0.0066 (9) |
C7 | 0.0671 (12) | 0.0451 (10) | 0.0611 (12) | −0.0002 (10) | 0.0131 (11) | 0.0154 (9) |
C8 | 0.0424 (8) | 0.0327 (8) | 0.0492 (9) | −0.0019 (7) | −0.0010 (7) | 0.0019 (7) |
C9 | 0.0416 (8) | 0.0333 (7) | 0.0437 (8) | −0.0026 (7) | 0.0015 (7) | 0.0009 (7) |
C10 | 0.0456 (9) | 0.0323 (8) | 0.0438 (8) | −0.0018 (7) | 0.0005 (7) | −0.0028 (7) |
C11 | 0.0681 (12) | 0.0370 (8) | 0.0612 (12) | 0.0062 (9) | 0.0215 (10) | 0.0096 (8) |
C12 | 0.0558 (11) | 0.0410 (9) | 0.0627 (12) | 0.0007 (9) | 0.0171 (10) | 0.0025 (9) |
C13 | 0.0432 (8) | 0.0369 (8) | 0.0484 (9) | 0.0040 (7) | −0.0047 (8) | −0.0039 (7) |
C14 | 0.0448 (9) | 0.0346 (8) | 0.0536 (10) | 0.0016 (7) | −0.0044 (8) | 0.0043 (8) |
C15 | 0.0757 (15) | 0.0357 (9) | 0.0883 (16) | 0.0063 (10) | 0.0100 (13) | 0.0084 (11) |
C16 | 0.0763 (14) | 0.0408 (10) | 0.0913 (17) | 0.0153 (10) | 0.0014 (14) | 0.0003 (12) |
C17 | 0.0491 (10) | 0.0463 (10) | 0.0654 (12) | 0.0104 (8) | −0.0066 (9) | −0.0098 (9) |
O17 | 0.0647 (8) | 0.0569 (9) | 0.0771 (10) | 0.0094 (8) | 0.0083 (8) | −0.0195 (8) |
C18 | 0.0584 (11) | 0.0564 (11) | 0.0524 (10) | 0.0148 (10) | −0.0081 (9) | −0.0075 (9) |
C19 | 0.0615 (12) | 0.0758 (15) | 0.0604 (12) | 0.0148 (12) | −0.0153 (10) | −0.0172 (12) |
Geometric parameters (Å, º) top
C1—O2 | 1.447 (2) | C11—H111 | 0.9700 |
C1—C10 | 1.523 (2) | C11—H112 | 0.9700 |
C1—H11 | 0.9700 | C12—C13 | 1.517 (2) |
C1—H12 | 0.9700 | C12—H121 | 0.9700 |
O2—C3 | 1.332 (3) | C12—H122 | 0.9700 |
C3—O3 | 1.220 (3) | C13—C19 | 1.522 (3) |
C3—C4 | 1.443 (3) | C13—C14 | 1.530 (3) |
C4—C5 | 1.335 (3) | C13—C17 | 1.536 (2) |
C4—H4 | 0.9300 | C14—C15 | 1.537 (3) |
C5—C6 | 1.495 (3) | C14—H14 | 0.9800 |
C5—C10 | 1.503 (3) | C15—C16 | 1.539 (3) |
C6—C7 | 1.522 (3) | C15—H151 | 0.9700 |
C6—H61 | 0.9700 | C15—H152 | 0.9700 |
C6—H62 | 0.9700 | C16—C17 | 1.530 (3) |
C7—C8 | 1.522 (3) | C16—H161 | 0.9700 |
C7—H71 | 0.9700 | C16—H162 | 0.9700 |
C7—H72 | 0.9700 | C17—O17 | 1.416 (3) |
C8—C14 | 1.519 (2) | C17—H171 | 0.9800 |
C8—C9 | 1.543 (2) | O17—H17 | 0.92 (3) |
C8—H8 | 0.9800 | C18—H181 | 0.9600 |
C9—C11 | 1.531 (3) | C18—H182 | 0.9600 |
C9—C10 | 1.561 (2) | C18—H183 | 0.9600 |
C9—H9 | 0.9800 | C19—H191 | 0.9600 |
C10—C18 | 1.536 (3) | C19—H192 | 0.9600 |
C11—C12 | 1.530 (3) | C19—H193 | 0.9600 |
| | | |
O2—C1—C10 | 114.03 (16) | H111—C11—H112 | 107.8 |
O2—C1—H11 | 108.7 | C13—C12—C11 | 111.31 (15) |
C10—C1—H11 | 108.7 | C13—C12—H121 | 109.4 |
O2—C1—H12 | 108.7 | C11—C12—H121 | 109.4 |
C10—C1—H12 | 108.7 | C13—C12—H122 | 109.4 |
H11—C1—H12 | 107.6 | C11—C12—H122 | 109.4 |
C3—O2—C1 | 117.04 (18) | H121—C12—H122 | 108.0 |
O3—C3—O2 | 117.9 (2) | C12—C13—C19 | 111.09 (18) |
O3—C3—C4 | 123.4 (2) | C12—C13—C14 | 107.48 (15) |
O2—C3—C4 | 118.41 (18) | C19—C13—C14 | 113.68 (16) |
C5—C4—C3 | 122.5 (2) | C12—C13—C17 | 115.37 (16) |
C5—C4—H4 | 118.8 | C19—C13—C17 | 109.39 (16) |
C3—C4—H4 | 118.8 | C14—C13—C17 | 99.43 (15) |
C4—C5—C6 | 121.96 (19) | C8—C14—C13 | 114.13 (14) |
C4—C5—C10 | 120.42 (18) | C8—C14—C15 | 118.70 (17) |
C6—C5—C10 | 117.50 (16) | C13—C14—C15 | 104.05 (17) |
C5—C6—C7 | 112.98 (17) | C8—C14—H14 | 106.4 |
C5—C6—H61 | 109.0 | C13—C14—H14 | 106.4 |
C7—C6—H61 | 109.0 | C15—C14—H14 | 106.4 |
C5—C6—H62 | 109.0 | C14—C15—C16 | 103.54 (18) |
C7—C6—H62 | 109.0 | C14—C15—H151 | 111.1 |
H61—C6—H62 | 107.8 | C16—C15—H151 | 111.1 |
C6—C7—C8 | 111.90 (17) | C14—C15—H152 | 111.1 |
C6—C7—H71 | 109.2 | C16—C15—H152 | 111.1 |
C8—C7—H71 | 109.2 | H151—C15—H152 | 109.0 |
C6—C7—H72 | 109.2 | C17—C16—C15 | 106.57 (17) |
C8—C7—H72 | 109.2 | C17—C16—H161 | 110.4 |
H71—C7—H72 | 107.9 | C15—C16—H161 | 110.4 |
C14—C8—C7 | 112.15 (16) | C17—C16—H162 | 110.4 |
C14—C8—C9 | 108.67 (14) | C15—C16—H162 | 110.4 |
C7—C8—C9 | 109.27 (15) | H161—C16—H162 | 108.6 |
C14—C8—H8 | 108.9 | O17—C17—C16 | 109.70 (18) |
C7—C8—H8 | 108.9 | O17—C17—C13 | 116.59 (18) |
C9—C8—H8 | 108.9 | C16—C17—C13 | 103.98 (17) |
C11—C9—C8 | 113.83 (15) | O17—C17—H171 | 108.8 |
C11—C9—C10 | 112.85 (15) | C16—C17—H171 | 108.8 |
C8—C9—C10 | 111.65 (14) | C13—C17—H171 | 108.8 |
C11—C9—H9 | 105.9 | C17—O17—H17 | 108.7 (19) |
C8—C9—H9 | 105.9 | C10—C18—H181 | 109.5 |
C10—C9—H9 | 105.9 | C10—C18—H182 | 109.5 |
C5—C10—C1 | 108.56 (15) | H181—C18—H182 | 109.5 |
C5—C10—C18 | 108.58 (16) | C10—C18—H183 | 109.5 |
C1—C10—C18 | 109.38 (17) | H181—C18—H183 | 109.5 |
C5—C10—C9 | 109.04 (15) | H182—C18—H183 | 109.5 |
C1—C10—C9 | 108.15 (15) | C13—C19—H191 | 109.5 |
C18—C10—C9 | 113.04 (14) | C13—C19—H192 | 109.5 |
C12—C11—C9 | 113.11 (16) | H191—C19—H192 | 109.5 |
C12—C11—H111 | 109.0 | C13—C19—H193 | 109.5 |
C9—C11—H111 | 109.0 | H191—C19—H193 | 109.5 |
C12—C11—H112 | 109.0 | H192—C19—H193 | 109.5 |
C9—C11—H112 | 109.0 | | |
(13) 6alpha-hydroxy-2-oxaandrost-4-ene-3,17-dione
top
Crystal data top
C18H24O4 | F(000) = 328 |
Mr = 304.37 | Dx = 1.271 Mg m−3 |
Monoclinic, P21 | Melting point = 244–246 K |
Hall symbol: P 2y1 | Cu Kα radiation, λ = 1.54178 Å |
a = 6.2214 (7) Å | Cell parameters from 43 reflections |
b = 12.050 (1) Å | θ = 25–50° |
c = 10.888 (1) Å | µ = 0.72 mm−1 |
β = 103.07 (1)° | T = 293 K |
V = 795.10 (13) Å3 | Plate, brown |
Z = 2 | 0.40 × 0.40 × 0.20 mm |
Data collection top
KM-4 diffractometer | Rint = 0.031 |
Radiation source: fine-focus sealed tube | θmax = 70.1°, θmin = 4.2° |
Graphite monochromator | h = −7→2 |
ω–2θ scans | k = −14→14 |
1624 measured reflections | l = −13→13 |
1596 independent reflections | 2 standard reflections every 100 reflections |
1458 reflections with I > 2σ(I) | intensity decay: less than 2 |
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)] = 0.036 | Riding |
wR(F2) = 0.105 | Calculated w = 1/[σ2(Fo2) + (0.0677P)2 + 0.099P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = −0.020 |
1512 reflections | Δρmax = 0.14 e Å−3 |
228 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (30) |
Crystal data top
C18H24O4 | V = 795.10 (13) Å3 |
Mr = 304.37 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 6.2214 (7) Å | µ = 0.72 mm−1 |
b = 12.050 (1) Å | T = 293 K |
c = 10.888 (1) Å | 0.40 × 0.40 × 0.20 mm |
β = 103.07 (1)° | |
Data collection top
KM-4 diffractometer | Rint = 0.031 |
1624 measured reflections | 2 standard reflections every 100 reflections |
1596 independent reflections | intensity decay: less than 2 |
1458 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | Riding |
wR(F2) = 0.105 | Δρmax = 0.14 e Å−3 |
S = 1.07 | Δρmin = −0.18 e Å−3 |
1512 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
228 parameters | Absolute structure parameter: −0.03 (30) |
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 2 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-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 | |
C1 | 0.2845 (6) | 0.2776 (2) | 0.2059 (3) | 0.0608 (7) | |
H11 | 0.3663 (6) | 0.2813 (2) | 0.1400 (3) | 0.077 (11)* | |
H12 | 0.1313 (6) | 0.2631 (2) | 0.1659 (3) | 0.073 (10)* | |
O2 | 0.2987 (4) | 0.3842 (2) | 0.2683 (2) | 0.0635 (5) | |
C3 | 0.2201 (4) | 0.3901 (2) | 0.3732 (3) | 0.0545 (6) | |
O3 | 0.1886 (4) | 0.4811 (2) | 0.4138 (3) | 0.0722 (6) | |
C4 | 0.1948 (4) | 0.2869 (2) | 0.4378 (3) | 0.0496 (6) | |
H4 | 0.1184 (4) | 0.2880 (2) | 0.5020 (3) | 0.058 (8)* | |
C5 | 0.2765 (3) | 0.1911 (2) | 0.4086 (2) | 0.0394 (5) | |
C6 | 0.2953 (4) | 0.0912 (2) | 0.4931 (2) | 0.0434 (5) | |
H61 | 0.4529 (4) | 0.0798 (2) | 0.5291 (2) | 0.051 (8)* | |
O6 | 0.1942 (4) | 0.1104 (2) | 0.5954 (2) | 0.0619 (6) | |
H6 | 0.080 (6) | 0.061 (4) | 0.589 (3) | 0.072 (10)* | |
C7 | 0.2113 (5) | −0.0129 (2) | 0.4182 (2) | 0.0447 (6) | |
H71 | 0.0535 (5) | −0.0066 (2) | 0.3849 (2) | 0.051 (7)* | |
H72 | 0.2378 (5) | −0.0768 (2) | 0.4737 (2) | 0.051 (8)* | |
C8 | 0.3261 (4) | −0.0297 (2) | 0.3098 (2) | 0.0375 (5) | |
H8 | 0.4850 (4) | −0.0381 (2) | 0.3441 (2) | 0.047 (7)* | |
C9 | 0.2857 (4) | 0.0724 (2) | 0.2217 (2) | 0.0405 (5) | |
H9 | 0.1253 (4) | 0.0807 (2) | 0.1948 (2) | 0.044 (7)* | |
C10 | 0.3724 (4) | 0.1813 (2) | 0.2928 (2) | 0.0411 (5) | |
C11 | 0.3701 (6) | 0.0563 (3) | 0.1003 (2) | 0.0571 (7) | |
H111 | 0.3199 (6) | 0.1180 (3) | 0.0439 (2) | 0.075 (10)* | |
H112 | 0.5301 (6) | 0.0576 (3) | 0.1215 (2) | 0.077 (11)* | |
C12 | 0.2925 (5) | −0.0525 (3) | 0.0309 (2) | 0.0565 (7) | |
H121 | 0.1344 (5) | −0.0498 (3) | −0.0030 (2) | 0.055 (8)* | |
H122 | 0.3641 (5) | −0.0620 (3) | −0.0388 (2) | 0.068 (9)* | |
C13 | 0.3483 (4) | −0.1495 (2) | 0.1208 (2) | 0.0447 (6) | |
C14 | 0.2402 (4) | −0.1317 (2) | 0.2326 (2) | 0.0398 (5) | |
H14 | 0.0836 (4) | −0.1178 (2) | 0.1962 (2) | 0.065 (9)* | |
C15 | 0.2522 (5) | −0.2458 (2) | 0.2960 (3) | 0.0535 (6) | |
H151 | 0.3975 (5) | −0.2590 (2) | 0.3492 (3) | 0.078 (11)* | |
H152 | 0.1427 (5) | −0.2525 (2) | 0.3464 (3) | 0.067 (9)* | |
C16 | 0.2039 (6) | −0.3259 (3) | 0.1841 (3) | 0.0660 (8) | |
H161 | 0.2973 (6) | −0.3911 (3) | 0.2018 (3) | 0.100 (14)* | |
H162 | 0.0508 (6) | −0.3493 (3) | 0.1660 (3) | 0.086 (11)* | |
C17 | 0.2531 (4) | −0.2614 (3) | 0.0736 (2) | 0.0505 (6) | |
O17 | 0.2192 (3) | −0.2936 (2) | −0.0342 (2) | 0.0667 (6) | |
C18 | 0.5999 (4) | −0.1692 (3) | 0.1616 (3) | 0.0628 (8) | |
H181 | 0.6708 (6) | −0.1031 (8) | 0.200 (2) | 0.094 (13)* | |
H182 | 0.6563 (8) | −0.187 (2) | 0.0890 (5) | 0.076 (10)* | |
H183 | 0.6289 (5) | −0.2294 (14) | 0.2208 (19) | 0.104 (15)* | |
C19 | 0.6254 (4) | 0.1873 (3) | 0.3332 (2) | 0.0518 (6) | |
H191 | 0.6791 (5) | 0.1267 (10) | 0.3891 (16) | 0.060 (9)* | |
H192 | 0.6683 (4) | 0.2563 (8) | 0.3758 (17) | 0.081 (11)* | |
H193 | 0.6867 (4) | 0.1825 (17) | 0.2600 (3) | 0.064 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.084 (2) | 0.0416 (14) | 0.0529 (14) | −0.0059 (14) | 0.0084 (13) | 0.0039 (12) |
O2 | 0.0825 (13) | 0.0383 (10) | 0.0695 (12) | −0.0025 (10) | 0.0167 (10) | 0.0040 (9) |
C3 | 0.0436 (12) | 0.0410 (14) | 0.077 (2) | 0.0023 (11) | 0.0109 (11) | −0.0024 (13) |
O3 | 0.0672 (12) | 0.0431 (11) | 0.110 (2) | 0.0065 (9) | 0.0284 (12) | −0.0067 (12) |
C4 | 0.0432 (12) | 0.0445 (13) | 0.0638 (14) | −0.0022 (10) | 0.0177 (10) | −0.0057 (13) |
C5 | 0.0339 (9) | 0.0391 (11) | 0.0453 (12) | −0.0057 (9) | 0.0090 (8) | −0.0049 (10) |
C6 | 0.0488 (12) | 0.0418 (13) | 0.0431 (11) | −0.0050 (10) | 0.0174 (9) | −0.0044 (10) |
O6 | 0.0818 (13) | 0.0590 (12) | 0.0556 (10) | −0.0205 (11) | 0.0384 (10) | −0.0171 (9) |
C7 | 0.0563 (13) | 0.0390 (12) | 0.0433 (12) | −0.0060 (10) | 0.0209 (10) | −0.0011 (10) |
C8 | 0.0374 (10) | 0.0387 (11) | 0.0371 (10) | −0.0008 (9) | 0.0101 (8) | −0.0003 (9) |
C9 | 0.0436 (11) | 0.0390 (12) | 0.0385 (11) | −0.0035 (10) | 0.0084 (8) | −0.0009 (10) |
C10 | 0.0438 (10) | 0.0405 (12) | 0.0399 (10) | −0.0053 (10) | 0.0115 (8) | −0.0003 (10) |
C11 | 0.085 (2) | 0.0498 (15) | 0.0411 (12) | −0.0125 (14) | 0.0232 (12) | −0.0014 (12) |
C12 | 0.075 (2) | 0.058 (2) | 0.0381 (11) | −0.0055 (14) | 0.0155 (11) | −0.0047 (12) |
C13 | 0.0400 (11) | 0.052 (2) | 0.0416 (11) | 0.0018 (10) | 0.0089 (9) | −0.0056 (11) |
C14 | 0.0371 (9) | 0.0406 (13) | 0.0418 (11) | −0.0006 (9) | 0.0093 (8) | −0.0009 (10) |
C15 | 0.070 (2) | 0.0402 (14) | 0.0523 (13) | −0.0026 (12) | 0.0172 (12) | 0.0000 (11) |
C16 | 0.086 (2) | 0.045 (2) | 0.067 (2) | −0.004 (2) | 0.0175 (15) | −0.0071 (15) |
C17 | 0.0457 (11) | 0.0518 (14) | 0.0520 (12) | 0.0093 (11) | 0.0068 (9) | −0.0102 (12) |
O17 | 0.0730 (12) | 0.0693 (15) | 0.0542 (10) | 0.0048 (10) | 0.0070 (8) | −0.0235 (10) |
C18 | 0.0408 (12) | 0.087 (2) | 0.063 (2) | 0.0030 (14) | 0.0170 (11) | −0.019 (2) |
C19 | 0.0456 (12) | 0.0581 (15) | 0.0555 (13) | −0.0133 (12) | 0.0196 (10) | −0.0064 (13) |
Geometric parameters (Å, º) top
C1—O2 | 1.446 (4) | C11—C12 | 1.536 (4) |
C1—C10 | 1.519 (4) | C11—H111 | 0.97 |
C1—H11 | 0.97 | C11—H112 | 0.97 |
C1—H12 | 0.97 | C12—C13 | 1.513 (4) |
O2—C3 | 1.342 (4) | C12—H121 | 0.97 |
C3—O3 | 1.215 (3) | C12—H122 | 0.97 |
C3—C4 | 1.454 (4) | C13—C17 | 1.515 (4) |
C4—C5 | 1.328 (4) | C13—C14 | 1.532 (3) |
C4—H4 | 0.93 | C13—C18 | 1.546 (3) |
C5—C6 | 1.503 (3) | C14—C15 | 1.532 (4) |
C5—C10 | 1.517 (3) | C14—H14 | 0.98 |
C6—O6 | 1.417 (3) | C15—C16 | 1.530 (4) |
C6—C7 | 1.522 (3) | C15—H151 | 0.97 |
C6—H61 | 0.98 | C15—H152 | 0.97 |
O6—H6 | 0.92 (4) | C16—C17 | 1.520 (4) |
C7—C8 | 1.525 (3) | C16—H161 | 0.97 |
C7—H71 | 0.97 | C16—H162 | 0.97 |
C7—H72 | 0.97 | C17—O17 | 1.209 (3) |
C8—C14 | 1.516 (3) | C18—H181 | 0.96 |
C8—C9 | 1.545 (3) | C18—H182 | 0.96 |
C8—H8 | 0.98 | C18—H183 | 0.96 |
C9—C11 | 1.541 (3) | C19—H191 | 0.96 |
C9—C10 | 1.557 (3) | C19—H192 | 0.96 |
C9—H9 | 0.98 | C19—H193 | 0.96 |
C10—C19 | 1.537 (3) | | |
| | | |
O2—C1—C10 | 114.2 (2) | C9—C11—H111 | 108.86 (15) |
O2—C1—H11 | 108.7 (2) | C12—C11—H112 | 108.9 (2) |
C10—C1—H11 | 108.7 (2) | C9—C11—H112 | 108.86 (14) |
O2—C1—H12 | 108.7 (2) | H111—C11—H112 | 107.7 |
C10—C1—H12 | 108.7 (2) | C13—C12—C11 | 109.9 (2) |
H11—C1—H12 | 107.6 | C13—C12—H121 | 109.68 (14) |
C3—O2—C1 | 116.8 (2) | C11—C12—H121 | 109.7 (2) |
O3—C3—O2 | 118.5 (3) | C13—C12—H122 | 109.69 (13) |
O3—C3—C4 | 123.5 (3) | C11—C12—H122 | 109.69 (14) |
O2—C3—C4 | 117.8 (2) | H121—C12—H122 | 108.2 |
C5—C4—C3 | 122.6 (2) | C12—C13—C17 | 116.9 (2) |
C5—C4—H4 | 118.71 (14) | C12—C13—C14 | 109.2 (2) |
C3—C4—H4 | 118.71 (15) | C17—C13—C14 | 100.7 (2) |
C4—C5—C6 | 122.1 (2) | C12—C13—C18 | 111.9 (2) |
C4—C5—C10 | 120.7 (2) | C17—C13—C18 | 104.7 (2) |
C6—C5—C10 | 117.1 (2) | C14—C13—C18 | 113.0 (2) |
O6—C6—C5 | 111.3 (2) | C8—C14—C13 | 113.0 (2) |
O6—C6—C7 | 113.3 (2) | C8—C14—C15 | 120.1 (2) |
C5—C6—C7 | 111.3 (2) | C13—C14—C15 | 104.3 (2) |
O6—C6—H61 | 106.85 (13) | C8—C14—H14 | 106.16 (11) |
C5—C6—H61 | 106.85 (11) | C13—C14—H14 | 106.16 (12) |
C7—C6—H61 | 106.85 (14) | C15—C14—H14 | 106.16 (14) |
C6—O6—H6 | 108 (2) | C16—C15—C14 | 103.1 (2) |
C6—C7—C8 | 111.1 (2) | C16—C15—H151 | 111.1 (2) |
C6—C7—H71 | 109.41 (13) | C14—C15—H151 | 111.15 (13) |
C8—C7—H71 | 109.41 (13) | C16—C15—H152 | 111.1 (2) |
C6—C7—H72 | 109.42 (13) | C14—C15—H152 | 111.15 (13) |
C8—C7—H72 | 109.41 (13) | H151—C15—H152 | 109.1 |
H71—C7—H72 | 108.0 | C17—C16—C15 | 105.6 (2) |
C14—C8—C7 | 111.7 (2) | C17—C16—H161 | 110.6 (2) |
C14—C8—C9 | 108.3 (2) | C15—C16—H161 | 110.6 (2) |
C7—C8—C9 | 109.6 (2) | C17—C16—H162 | 110.6 (2) |
C14—C8—H8 | 109.08 (11) | C15—C16—H162 | 110.6 (2) |
C7—C8—H8 | 109.08 (13) | H161—C16—H162 | 108.8 |
C9—C8—H8 | 109.08 (11) | O17—C17—C13 | 125.8 (3) |
C11—C9—C8 | 113.1 (2) | O17—C17—C16 | 125.6 (3) |
C11—C9—C10 | 112.7 (2) | C13—C17—C16 | 108.7 (2) |
C8—C9—C10 | 111.9 (2) | C13—C18—H181 | 109.5 (2) |
C11—C9—H9 | 106.13 (14) | C13—C18—H182 | 109.47 (14) |
C8—C9—H9 | 106.13 (11) | H181—C18—H182 | 109.5 |
C10—C9—H9 | 106.13 (12) | C13—C18—H183 | 109.5 (2) |
C5—C10—C1 | 107.7 (2) | H181—C18—H183 | 109.5 |
C5—C10—C19 | 109.2 (2) | H182—C18—H183 | 109.5 |
C1—C10—C19 | 110.1 (2) | C10—C19—H191 | 109.47 (15) |
C5—C10—C9 | 108.8 (2) | C10—C19—H192 | 109.47 (15) |
C1—C10—C9 | 107.4 (2) | H191—C19—H192 | 109.5 |
C19—C10—C9 | 113.5 (2) | C10—C19—H193 | 109.47 (12) |
C12—C11—C9 | 113.6 (2) | H191—C19—H193 | 109.5 |
C12—C11—H111 | 108.86 (15) | H192—C19—H193 | 109.5 |
| | | |
C10—C1—O2—C3 | −49.7 (4) | C8—C9—C10—C1 | −168.8 (2) |
C1—O2—C3—O3 | −165.6 (3) | C11—C9—C10—C19 | −59.6 (3) |
C1—O2—C3—C4 | 19.4 (4) | C8—C9—C10—C19 | 69.2 (2) |
O3—C3—C4—C5 | −164.2 (3) | C8—C9—C11—C12 | 49.9 (3) |
O2—C3—C4—C5 | 10.5 (4) | C10—C9—C11—C12 | 178.1 (2) |
C3—C4—C5—C6 | 165.9 (2) | C9—C11—C12—C13 | −52.8 (3) |
C3—C4—C5—C10 | −9.1 (4) | C11—C12—C13—C17 | 171.0 (2) |
C4—C5—C6—O6 | 6.5 (3) | C11—C12—C13—C14 | 57.6 (3) |
C10—C5—C6—O6 | −178.4 (2) | C11—C12—C13—C18 | −68.3 (3) |
C4—C5—C6—C7 | 133.9 (2) | C7—C8—C14—C13 | 178.6 (2) |
C10—C5—C6—C7 | −51.0 (3) | C9—C8—C14—C13 | 57.8 (2) |
O6—C6—C7—C8 | −179.8 (2) | C7—C8—C14—C15 | −57.6 (3) |
C5—C6—C7—C8 | 53.9 (3) | C9—C8—C14—C15 | −178.3 (2) |
C6—C7—C8—C14 | −178.7 (2) | C12—C13—C14—C8 | −63.0 (2) |
C6—C7—C8—C9 | −58.7 (3) | C17—C13—C14—C8 | 173.4 (2) |
C14—C8—C9—C11 | −50.5 (2) | C18—C13—C14—C8 | 62.3 (3) |
C7—C8—C9—C11 | −172.5 (2) | C12—C13—C14—C15 | 164.9 (2) |
C14—C8—C9—C10 | −179.1 (2) | C17—C13—C14—C15 | 41.2 (2) |
C7—C8—C9—C10 | 58.8 (2) | C18—C13—C14—C15 | −69.9 (3) |
C4—C5—C10—C1 | −19.2 (3) | C8—C14—C15—C16 | −166.9 (2) |
C6—C5—C10—C1 | 165.6 (2) | C13—C14—C15—C16 | −39.0 (3) |
C4—C5—C10—C19 | 100.4 (3) | C14—C15—C16—C17 | 20.6 (3) |
C6—C5—C10—C19 | −74.8 (3) | C12—C13—C17—O17 | 32.7 (4) |
C4—C5—C10—C9 | −135.3 (2) | C14—C13—C17—O17 | 150.8 (3) |
C6—C5—C10—C9 | 49.5 (2) | C18—C13—C17—O17 | −91.8 (3) |
O2—C1—C10—C5 | 47.1 (3) | C12—C13—C17—C16 | −146.5 (2) |
O2—C1—C10—C19 | −71.8 (3) | C14—C13—C17—C16 | −28.4 (3) |
O2—C1—C10—C9 | 164.1 (2) | C18—C13—C17—C16 | 89.1 (3) |
C11—C9—C10—C5 | 178.6 (2) | C15—C16—C17—O17 | −174.1 (3) |
C8—C9—C10—C5 | −52.5 (2) | C15—C16—C17—C13 | 5.0 (3) |
C11—C9—C10—C1 | 62.3 (3) | | |
(14) 6-hydroxy-2-oxa-5beta-androstane-3,17-dione
top
Crystal data top
C18H26O4 | Dx = 1.244 Mg m−3 |
Mr = 306.39 | Melting point = 235–238 K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 56 reflections |
a = 6.335 (1) Å | θ = 16–42° |
b = 9.482 (1) Å | µ = 0.70 mm−1 |
c = 27.245 (6) Å | T = 293 K |
V = 1636.6 (5) Å3 | Plate, colourless |
Z = 4 | 0.3 × 0.2 × 0.1 mm |
F(000) = 664 | |
Data collection top
KM-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 65.1°, θmin = 3.2° |
Graphite monochromator | h = 0→7 |
ω–2θ scans | k = 0→10 |
1586 measured reflections | l = 0→32 |
1586 independent reflections | 2 standard reflections every 100 reflections |
913 reflections with I > 2σ(I) | intensity decay: less than 2.3% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0573P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.104 | (Δ/σ)max = 0.001 |
S = 0.98 | Δρmax = 0.14 e Å−3 |
1586 reflections | Δρmin = −0.13 e Å−3 |
231 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0015 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.0 (5) |
Crystal data top
C18H26O4 | V = 1636.6 (5) Å3 |
Mr = 306.39 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 6.335 (1) Å | µ = 0.70 mm−1 |
b = 9.482 (1) Å | T = 293 K |
c = 27.245 (6) Å | 0.3 × 0.2 × 0.1 mm |
Data collection top
KM-4 diffractometer | Rint = 0.000 |
1586 measured reflections | 2 standard reflections every 100 reflections |
1586 independent reflections | intensity decay: less than 2.3% |
913 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | Δρmax = 0.14 e Å−3 |
S = 0.98 | Δρmin = −0.13 e Å−3 |
1586 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
231 parameters | Absolute structure parameter: 0.0 (5) |
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 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 | |
C1 | −0.1627 (7) | 0.0346 (4) | 0.16963 (13) | 0.0607 (12) | |
H11 | −0.2474 | −0.0424 | 0.1824 | 0.049 (11)* | |
H12 | −0.0888 | −0.0002 | 0.1409 | 0.074 (13)* | |
O2 | −0.0088 (4) | 0.0724 (3) | 0.20611 (10) | 0.0678 (9) | |
C3 | −0.0682 (8) | 0.1548 (5) | 0.24375 (15) | 0.0629 (12) | |
O3 | 0.0597 (5) | 0.1700 (4) | 0.27636 (10) | 0.0916 (11) | |
C4 | −0.2735 (7) | 0.2286 (5) | 0.24298 (12) | 0.0593 (11) | |
H41 | −0.2452 | 0.3291 | 0.2434 | 0.12 (2)* | |
H42 | −0.3463 | 0.2061 | 0.2733 | 0.066 (12)* | |
C5 | −0.4261 (6) | 0.1996 (4) | 0.20056 (11) | 0.0469 (9) | |
H51 | −0.5180 | 0.1218 | 0.2107 | 0.060 (12)* | |
C6 | −0.5674 (7) | 0.3273 (4) | 0.19073 (12) | 0.0515 (10) | |
H61 | −0.6776 | 0.2994 | 0.1674 | 0.062 (12)* | |
O6 | −0.6667 (5) | 0.3755 (3) | 0.23476 (10) | 0.0722 (10) | |
H6 | −0.745 (11) | 0.315 (6) | 0.2501 (19) | 0.14 (3)* | |
C7 | −0.4470 (7) | 0.4506 (4) | 0.16920 (12) | 0.0521 (10) | |
H71 | −0.3497 | 0.4869 | 0.1936 | 0.057 (11)* | |
H72 | −0.5456 | 0.5253 | 0.1611 | 0.074 (13)* | |
C8 | −0.3240 (6) | 0.4097 (4) | 0.12334 (11) | 0.0432 (9) | |
H81 | −0.4254 | 0.3898 | 0.0971 | 0.044 (9)* | |
C9 | −0.1868 (6) | 0.2770 (4) | 0.13117 (10) | 0.0424 (9) | |
H91 | −0.0796 | 0.3033 | 0.1554 | 0.044 (9)* | |
C10 | −0.3097 (6) | 0.1523 (4) | 0.15371 (11) | 0.0467 (10) | |
C11 | −0.0656 (8) | 0.2397 (4) | 0.08390 (13) | 0.0567 (11) | |
H111 | 0.0266 | 0.1602 | 0.0904 | 0.065 (12)* | |
H112 | −0.1658 | 0.2111 | 0.0589 | 0.063 (12)* | |
C12 | 0.0664 (8) | 0.3623 (4) | 0.06433 (14) | 0.0622 (11) | |
H121 | 0.1806 | 0.3819 | 0.0870 | 0.083 (15)* | |
H122 | 0.1280 | 0.3360 | 0.0330 | 0.085 (14)* | |
C13 | −0.0660 (6) | 0.4938 (4) | 0.05778 (11) | 0.0490 (9) | |
C14 | −0.1800 (6) | 0.5273 (4) | 0.10631 (11) | 0.0466 (10) | |
H141 | −0.0682 | 0.5328 | 0.1311 | 0.043 (9)* | |
C15 | −0.2553 (8) | 0.6795 (4) | 0.09900 (15) | 0.0611 (12) | |
H151 | −0.3783 | 0.6834 | 0.0778 | 0.068 (14)* | |
H152 | −0.2885 | 0.7239 | 0.1301 | 0.080 (14)* | |
C16 | −0.0637 (9) | 0.7488 (5) | 0.07470 (17) | 0.0726 (13) | |
H161 | −0.1081 | 0.8189 | 0.0509 | 0.115 (18)* | |
H162 | 0.0251 | 0.7939 | 0.0991 | 0.100 (17)* | |
C17 | 0.0528 (8) | 0.6305 (5) | 0.04984 (14) | 0.0647 (12) | |
O17 | 0.2216 (6) | 0.6411 (4) | 0.02880 (12) | 0.1031 (13) | |
C18 | −0.4655 (7) | 0.0859 (5) | 0.11724 (14) | 0.0656 (12) | |
H181 | −0.5594 | 0.0238 | 0.1345 | 0.12 (2)* | |
H182 | −0.3888 | 0.0335 | 0.0929 | 0.083 (14)* | |
H183 | −0.5457 | 0.1590 | 0.1015 | 0.093 (17)* | |
C19 | −0.2197 (9) | 0.4808 (6) | 0.01356 (12) | 0.0744 (15) | |
H191 | −0.3110 | 0.4011 | 0.0184 | 0.11 (2)* | |
H192 | −0.1401 | 0.4681 | −0.0161 | 0.13 (2)* | |
H193 | −0.3030 | 0.5650 | 0.0111 | 0.11 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.075 (3) | 0.052 (3) | 0.055 (2) | 0.008 (3) | 0.009 (3) | 0.007 (2) |
O2 | 0.0600 (19) | 0.080 (2) | 0.0635 (17) | 0.0082 (17) | −0.0039 (16) | 0.0202 (16) |
C3 | 0.065 (3) | 0.071 (3) | 0.052 (2) | −0.017 (3) | −0.008 (2) | 0.025 (2) |
O3 | 0.078 (2) | 0.118 (3) | 0.079 (2) | −0.016 (2) | −0.030 (2) | 0.0286 (19) |
C4 | 0.066 (3) | 0.073 (3) | 0.039 (2) | −0.007 (3) | −0.001 (2) | 0.004 (2) |
C5 | 0.050 (2) | 0.051 (2) | 0.0397 (18) | −0.008 (2) | 0.0016 (19) | 0.0017 (16) |
C6 | 0.043 (2) | 0.065 (3) | 0.0462 (18) | 0.000 (2) | 0.011 (2) | −0.007 (2) |
O6 | 0.076 (2) | 0.076 (2) | 0.0649 (17) | −0.0027 (19) | 0.0332 (17) | −0.0112 (16) |
C7 | 0.059 (3) | 0.052 (2) | 0.046 (2) | 0.002 (3) | 0.005 (2) | −0.0034 (18) |
C8 | 0.046 (2) | 0.048 (2) | 0.0353 (17) | 0.004 (2) | 0.0032 (18) | −0.0050 (16) |
C9 | 0.045 (2) | 0.048 (2) | 0.0339 (17) | 0.007 (2) | −0.0005 (17) | −0.0036 (16) |
C10 | 0.056 (2) | 0.043 (2) | 0.0403 (17) | −0.002 (2) | −0.002 (2) | −0.0047 (17) |
C11 | 0.069 (3) | 0.052 (3) | 0.050 (2) | 0.020 (3) | 0.016 (2) | −0.0003 (19) |
C12 | 0.067 (3) | 0.070 (3) | 0.050 (2) | 0.013 (3) | 0.022 (2) | 0.009 (2) |
C13 | 0.056 (2) | 0.055 (2) | 0.0363 (17) | 0.004 (2) | 0.006 (2) | 0.0038 (17) |
C14 | 0.055 (2) | 0.051 (2) | 0.0346 (17) | 0.004 (2) | −0.0002 (19) | 0.0008 (16) |
C15 | 0.084 (3) | 0.046 (2) | 0.053 (2) | 0.009 (3) | 0.007 (3) | −0.0016 (19) |
C16 | 0.096 (4) | 0.055 (3) | 0.067 (3) | −0.002 (3) | 0.006 (3) | 0.006 (2) |
C17 | 0.077 (3) | 0.065 (3) | 0.051 (2) | −0.006 (3) | 0.006 (3) | 0.012 (2) |
O17 | 0.091 (3) | 0.101 (3) | 0.117 (3) | −0.003 (2) | 0.041 (2) | 0.029 (2) |
C18 | 0.080 (3) | 0.061 (3) | 0.055 (2) | −0.006 (3) | −0.006 (3) | −0.010 (2) |
C19 | 0.105 (4) | 0.078 (4) | 0.040 (2) | 0.014 (4) | −0.003 (2) | −0.002 (2) |
Geometric parameters (Å, º) top
C1—O2 | 1.438 (5) | C10—C18 | 1.535 (5) |
C1—C10 | 1.517 (5) | C11—C12 | 1.528 (5) |
C1—H11 | 0.9700 | C11—H111 | 0.9700 |
C1—H12 | 0.9700 | C11—H112 | 0.9700 |
O2—C3 | 1.343 (5) | C12—C13 | 1.513 (5) |
C3—O3 | 1.211 (5) | C12—H121 | 0.9700 |
C3—C4 | 1.477 (6) | C12—H122 | 0.9700 |
C4—C5 | 1.532 (5) | C13—C17 | 1.515 (6) |
C4—H41 | 0.9700 | C13—C14 | 1.540 (4) |
C4—H42 | 0.9700 | C13—C19 | 1.554 (5) |
C5—C6 | 1.529 (5) | C14—C15 | 1.533 (5) |
C5—C10 | 1.541 (5) | C14—H141 | 0.9800 |
C5—H51 | 0.9800 | C15—C16 | 1.531 (6) |
C6—O6 | 1.429 (4) | C15—H151 | 0.9700 |
C6—C7 | 1.514 (5) | C15—H152 | 0.9700 |
C6—H61 | 0.9800 | C16—C17 | 1.504 (6) |
O6—H6 | 0.87 (6) | C16—H161 | 0.9700 |
C7—C8 | 1.523 (4) | C16—H162 | 0.9700 |
C7—H71 | 0.9700 | C17—O17 | 1.218 (5) |
C7—H72 | 0.9700 | C18—H181 | 0.9600 |
C8—C14 | 1.514 (5) | C18—H182 | 0.9600 |
C8—C9 | 1.544 (5) | C18—H183 | 0.9600 |
C8—H81 | 0.9800 | C19—H191 | 0.9600 |
C9—C11 | 1.541 (4) | C19—H192 | 0.9600 |
C9—C10 | 1.543 (5) | C19—H193 | 0.9600 |
C9—H91 | 0.9800 | | |
| | | |
O2—C1—C10 | 115.5 (3) | C5—C10—C9 | 110.4 (3) |
O2—C1—H11 | 108.4 | C12—C11—C9 | 112.9 (3) |
C10—C1—H11 | 108.4 | C12—C11—H111 | 109.0 |
O2—C1—H12 | 108.4 | C9—C11—H111 | 109.0 |
C10—C1—H12 | 108.4 | C12—C11—H112 | 109.0 |
H11—C1—H12 | 107.5 | C9—C11—H112 | 109.0 |
C3—O2—C1 | 118.9 (3) | H111—C11—H112 | 107.8 |
O3—C3—O2 | 116.2 (5) | C13—C12—C11 | 111.4 (4) |
O3—C3—C4 | 122.9 (4) | C13—C12—H121 | 109.4 |
O2—C3—C4 | 120.8 (4) | C11—C12—H121 | 109.4 |
C3—C4—C5 | 118.8 (3) | C13—C12—H122 | 109.4 |
C3—C4—H41 | 107.6 | C11—C12—H122 | 109.4 |
C5—C4—H41 | 107.6 | H121—C12—H122 | 108.0 |
C3—C4—H42 | 107.6 | C12—C13—C17 | 116.5 (4) |
C5—C4—H42 | 107.6 | C12—C13—C14 | 109.2 (3) |
H41—C4—H42 | 107.0 | C17—C13—C14 | 100.3 (3) |
C6—C5—C4 | 111.1 (3) | C12—C13—C19 | 111.9 (4) |
C6—C5—C10 | 111.5 (3) | C17—C13—C19 | 105.6 (3) |
C4—C5—C10 | 112.0 (3) | C14—C13—C19 | 112.9 (3) |
C6—C5—H51 | 107.3 | C8—C14—C15 | 123.1 (3) |
C4—C5—H51 | 107.3 | C8—C14—C13 | 113.2 (3) |
C10—C5—H51 | 107.3 | C15—C14—C13 | 103.2 (3) |
O6—C6—C7 | 107.5 (3) | C8—C14—H141 | 105.3 |
O6—C6—C5 | 111.3 (3) | C15—C14—H141 | 105.3 |
C7—C6—C5 | 112.6 (3) | C13—C14—H141 | 105.3 |
O6—C6—H61 | 108.4 | C16—C15—C14 | 102.3 (3) |
C7—C6—H61 | 108.4 | C16—C15—H151 | 111.3 |
C5—C6—H61 | 108.4 | C14—C15—H151 | 111.3 |
C6—O6—H6 | 116 (4) | C16—C15—H152 | 111.3 |
C6—C7—C8 | 112.3 (3) | C14—C15—H152 | 111.3 |
C6—C7—H71 | 109.2 | H151—C15—H152 | 109.2 |
C8—C7—H71 | 109.2 | C17—C16—C15 | 105.3 (4) |
C6—C7—H72 | 109.2 | C17—C16—H161 | 110.7 |
C8—C7—H72 | 109.2 | C15—C16—H161 | 110.7 |
H71—C7—H72 | 107.9 | C17—C16—H162 | 110.7 |
C14—C8—C7 | 111.8 (3) | C15—C16—H162 | 110.7 |
C14—C8—C9 | 107.7 (3) | H161—C16—H162 | 108.8 |
C7—C8—C9 | 112.5 (3) | O17—C17—C16 | 125.6 (5) |
C14—C8—H81 | 108.2 | O17—C17—C13 | 125.1 (4) |
C7—C8—H81 | 108.2 | C16—C17—C13 | 109.3 (4) |
C9—C8—H81 | 108.2 | C10—C18—H181 | 109.5 |
C11—C9—C10 | 114.1 (3) | C10—C18—H182 | 109.5 |
C11—C9—C8 | 110.6 (3) | H181—C18—H182 | 109.5 |
C10—C9—C8 | 113.3 (3) | C10—C18—H183 | 109.5 |
C11—C9—H91 | 106.0 | H181—C18—H183 | 109.5 |
C10—C9—H91 | 106.0 | H182—C18—H183 | 109.5 |
C8—C9—H91 | 106.0 | C13—C19—H191 | 109.5 |
C1—C10—C18 | 106.1 (3) | C13—C19—H192 | 109.5 |
C1—C10—C5 | 105.7 (3) | H191—C19—H192 | 109.5 |
C18—C10—C5 | 110.4 (3) | C13—C19—H193 | 109.5 |
C1—C10—C9 | 111.6 (3) | H191—C19—H193 | 109.5 |
C18—C10—C9 | 112.4 (3) | H192—C19—H193 | 109.5 |
(15) 6,17-dihydroxy-2-oxaandrost-4-ene-3-one
top
Crystal data top
C18H26O4 | Dx = 1.275 Mg m−3 |
Mr = 306.39 | Melting point = 227–230 K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 56 reflections |
a = 9.3361 (7) Å | θ = 13–72° |
b = 9.6261 (7) Å | µ = 0.71 mm−1 |
c = 17.764 (2) Å | T = 293 K |
V = 1596.5 (2) Å3 | Prism, white |
Z = 4 | 0.5 × 0.4 × 0.2 mm |
F(000) = 664 | |
Data collection top
KM-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 70.1°, θmin = 5.0° |
Graphite monochromator | h = 0→11 |
ω–2θ scans | k = 0→11 |
1746 measured reflections | l = 0→21 |
1746 independent reflections | 2 standard reflections every 100 reflections |
1634 reflections with I > 2σ(I) | intensity decay: less than 1% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | Riding |
R[F2 > 2σ(F2)] = 0.031 | Calculated w = 1/[σ2(Fo2) + (0.0538P)2 + 0.2314P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.102 | (Δ/σ)max = 0.042 |
S = 1.06 | Δρmax = 0.17 e Å−3 |
1741 reflections | Δρmin = −0.11 e Å−3 |
234 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0007 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.06 (28) |
Crystal data top
C18H26O4 | V = 1596.5 (2) Å3 |
Mr = 306.39 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 9.3361 (7) Å | µ = 0.71 mm−1 |
b = 9.6261 (7) Å | T = 293 K |
c = 17.764 (2) Å | 0.5 × 0.4 × 0.2 mm |
Data collection top
KM-4 diffractometer | Rint = 0.000 |
1746 measured reflections | 2 standard reflections every 100 reflections |
1746 independent reflections | intensity decay: less than 1% |
1634 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | Riding |
wR(F2) = 0.102 | Δρmax = 0.17 e Å−3 |
S = 1.06 | Δρmin = −0.11 e Å−3 |
1741 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
234 parameters | Absolute structure parameter: 0.06 (28) |
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 5 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-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 | |
C1 | 0.2964 (2) | 0.8623 (2) | 0.86551 (14) | 0.0459 (5) | |
H11 | 0.2591 (2) | 0.9448 (2) | 0.89004 (14) | 0.064 (8)* | |
H12 | 0.3032 (2) | 0.8820 (2) | 0.81207 (14) | 0.054 (7)* | |
O2 | 0.19615 (14) | 0.7488 (2) | 0.87671 (10) | 0.0522 (4) | |
C3 | 0.2404 (2) | 0.6214 (2) | 0.85772 (12) | 0.0448 (5) | |
O3 | 0.1531 (2) | 0.5281 (2) | 0.85524 (11) | 0.0643 (5) | |
C4 | 0.3931 (2) | 0.5997 (2) | 0.84450 (11) | 0.0403 (4) | |
H41 | 0.4228 (2) | 0.5180 (2) | 0.82133 (11) | 0.053 (7)* | |
C5 | 0.4916 (2) | 0.6931 (2) | 0.86450 (10) | 0.0337 (4) | |
C6 | 0.6480 (2) | 0.6589 (2) | 0.86318 (13) | 0.0406 (5) | |
H61 | 0.6774 (2) | 0.6370 (2) | 0.91479 (13) | 0.035 (5)* | |
O6 | 0.6718 (2) | 0.5394 (2) | 0.81851 (12) | 0.0636 (5) | |
H6O | 0.753 (5) | 0.490 (4) | 0.848 (2) | 0.108 (12)* | |
C7 | 0.7391 (2) | 0.7799 (2) | 0.83602 (13) | 0.0416 (5) | |
H71 | 0.7225 (2) | 0.7943 (2) | 0.78268 (13) | 0.046 (6)* | |
H72 | 0.8396 (2) | 0.7574 (2) | 0.84279 (13) | 0.049 (6)* | |
C8 | 0.7050 (2) | 0.9134 (2) | 0.87846 (10) | 0.0303 (4) | |
H81 | 0.7231 (2) | 0.8992 (2) | 0.93226 (10) | 0.031 (5)* | |
C9 | 0.5460 (2) | 0.9506 (2) | 0.86688 (10) | 0.0296 (4) | |
H91 | 0.5311 (2) | 0.9562 (2) | 0.81235 (10) | 0.034 (5)* | |
C10 | 0.4458 (2) | 0.8329 (2) | 0.89578 (10) | 0.0324 (4) | |
C11 | 0.5067 (2) | 1.0936 (2) | 0.89874 (13) | 0.0433 (5) | |
H111 | 0.5080 (2) | 1.0889 (2) | 0.95328 (13) | 0.060 (7)* | |
H112 | 0.4099 (2) | 1.1166 (2) | 0.88331 (13) | 0.059 (7)* | |
C12 | 0.6082 (2) | 1.2096 (2) | 0.87294 (13) | 0.0418 (5) | |
H121 | 0.5962 (2) | 1.2249 (2) | 0.81933 (13) | 0.044 (6)* | |
H122 | 0.5840 (2) | 1.2951 (2) | 0.89881 (13) | 0.051 (7)* | |
C13 | 0.7647 (2) | 1.1720 (2) | 0.88936 (10) | 0.0330 (4) | |
C14 | 0.7962 (2) | 1.0335 (2) | 0.85058 (11) | 0.0326 (4) | |
H141 | 0.7715 (2) | 1.0464 (2) | 0.79743 (11) | 0.030 (5)* | |
C15 | 0.9602 (2) | 1.0202 (2) | 0.8536 (2) | 0.0484 (5) | |
H151 | 0.9958 (2) | 0.9673 (2) | 0.8110 (2) | 0.070 (8)* | |
H152 | 0.9907 (2) | 0.9754 (2) | 0.8998 (2) | 0.056 (7)* | |
C16 | 1.0134 (2) | 1.1722 (2) | 0.8504 (2) | 0.0513 (6) | |
H161 | 1.0723 (2) | 1.1935 (2) | 0.8939 (2) | 0.074 (9)* | |
H162 | 1.0693 (2) | 1.1881 (2) | 0.8051 (2) | 0.086 (10)* | |
C17 | 0.8778 (2) | 1.2619 (2) | 0.85001 (11) | 0.0388 (4) | |
H171 | 0.8480 (2) | 1.2761 (2) | 0.79766 (11) | 0.053 (7)* | |
O17 | 0.8934 (2) | 1.39449 (15) | 0.88491 (10) | 0.0542 (4) | |
H17O | 0.973 (3) | 1.429 (3) | 0.8692 (15) | 0.054 (7)* | |
C18 | 0.7926 (3) | 1.1699 (3) | 0.97428 (12) | 0.0525 (5) | |
H181 | 0.7265 (14) | 1.1073 (15) | 0.9981 (2) | 0.097 (11)* | |
H182 | 0.7799 (19) | 1.2616 (5) | 0.9944 (2) | 0.066 (7)* | |
H183 | 0.8889 (7) | 1.1393 (18) | 0.98360 (12) | 0.083 (9)* | |
C19 | 0.4428 (3) | 0.8221 (2) | 0.98248 (11) | 0.0505 (5) | |
H191 | 0.3802 (13) | 0.7478 (10) | 0.99723 (11) | 0.044 (5)* | |
H192 | 0.4085 (15) | 0.9079 (6) | 1.00336 (12) | 0.071 (8)* | |
H193 | 0.5377 (4) | 0.8039 (15) | 1.00078 (12) | 0.077 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0265 (9) | 0.0406 (10) | 0.0705 (14) | −0.0075 (8) | 0.0005 (10) | 0.0023 (10) |
O2 | 0.0274 (6) | 0.0489 (8) | 0.0802 (10) | −0.0116 (6) | 0.0051 (7) | 0.0000 (8) |
C3 | 0.0392 (10) | 0.0500 (11) | 0.0452 (10) | −0.0164 (9) | −0.0017 (9) | −0.0001 (9) |
O3 | 0.0499 (9) | 0.0621 (10) | 0.0810 (11) | −0.0315 (8) | 0.0037 (9) | −0.0039 (9) |
C4 | 0.0403 (9) | 0.0357 (9) | 0.0449 (10) | −0.0081 (9) | 0.0004 (8) | −0.0023 (8) |
C5 | 0.0335 (9) | 0.0311 (8) | 0.0364 (9) | −0.0044 (7) | −0.0009 (8) | 0.0034 (7) |
C6 | 0.0361 (10) | 0.0257 (8) | 0.0600 (12) | 0.0008 (7) | −0.0065 (9) | −0.0008 (9) |
O6 | 0.0516 (9) | 0.0343 (7) | 0.1048 (14) | 0.0036 (7) | −0.0029 (10) | −0.0181 (9) |
C7 | 0.0281 (9) | 0.0326 (9) | 0.0640 (12) | 0.0006 (8) | 0.0045 (9) | −0.0066 (9) |
C8 | 0.0238 (8) | 0.0265 (8) | 0.0406 (8) | 0.0002 (7) | −0.0004 (7) | −0.0003 (7) |
C9 | 0.0237 (8) | 0.0277 (8) | 0.0373 (8) | −0.0011 (7) | 0.0005 (7) | 0.0007 (7) |
C10 | 0.0266 (8) | 0.0328 (9) | 0.0379 (9) | −0.0037 (8) | 0.0020 (7) | 0.0004 (7) |
C11 | 0.0276 (9) | 0.0313 (10) | 0.0708 (13) | −0.0004 (8) | 0.0092 (9) | −0.0054 (9) |
C12 | 0.0306 (9) | 0.0280 (8) | 0.0667 (13) | 0.0000 (8) | 0.0050 (9) | −0.0012 (9) |
C13 | 0.0258 (8) | 0.0284 (9) | 0.0446 (9) | −0.0041 (7) | 0.0023 (7) | −0.0022 (7) |
C14 | 0.0243 (8) | 0.0304 (8) | 0.0432 (9) | 0.0004 (7) | 0.0024 (7) | 0.0013 (8) |
C15 | 0.0234 (9) | 0.0375 (10) | 0.084 (2) | −0.0022 (8) | 0.0049 (10) | −0.0002 (11) |
C16 | 0.0285 (9) | 0.0425 (11) | 0.083 (2) | −0.0055 (8) | 0.0083 (11) | 0.0006 (12) |
C17 | 0.0300 (8) | 0.0330 (8) | 0.0533 (10) | −0.0060 (8) | 0.0025 (8) | 0.0004 (9) |
O17 | 0.0407 (8) | 0.0343 (7) | 0.0876 (12) | −0.0137 (7) | 0.0088 (8) | −0.0083 (7) |
C18 | 0.0555 (14) | 0.0566 (12) | 0.0453 (10) | −0.0171 (11) | −0.0002 (10) | −0.0071 (10) |
C19 | 0.0619 (14) | 0.0487 (11) | 0.0410 (10) | −0.0171 (11) | 0.0110 (10) | −0.0008 (9) |
Geometric parameters (Å, º) top
C1—O2 | 1.453 (2) | C11—H111 | 0.97 |
C1—C10 | 1.521 (3) | C11—H112 | 0.97 |
C1—H11 | 0.97 | C12—C13 | 1.533 (3) |
C1—H12 | 0.97 | C12—H121 | 0.97 |
O2—C3 | 1.338 (3) | C12—H122 | 0.97 |
C3—O3 | 1.213 (3) | C13—C14 | 1.529 (2) |
C3—C4 | 1.460 (3) | C13—C18 | 1.531 (3) |
C4—C5 | 1.334 (3) | C13—C17 | 1.533 (2) |
C4—H41 | 0.93 | C14—C15 | 1.537 (2) |
C5—C6 | 1.497 (3) | C14—H141 | 0.98 |
C5—C10 | 1.518 (2) | C15—C16 | 1.546 (3) |
C6—O6 | 1.415 (2) | C15—H151 | 0.97 |
C6—C7 | 1.521 (3) | C15—H152 | 0.97 |
C6—H61 | 0.98 | C16—C17 | 1.533 (3) |
O6—H6O | 1.04 (4) | C16—H161 | 0.97 |
C7—C8 | 1.524 (2) | C16—H162 | 0.97 |
C7—H71 | 0.97 | C17—O17 | 1.427 (2) |
C7—H72 | 0.97 | C17—H171 | 0.98 |
C8—C14 | 1.518 (2) | O17—H17O | 0.86 (3) |
C8—C9 | 1.541 (2) | C18—H181 | 0.96 |
C8—H81 | 0.98 | C18—H182 | 0.96 |
C9—C11 | 1.533 (2) | C18—H183 | 0.96 |
C9—C10 | 1.556 (2) | C19—H191 | 0.96 |
C9—H91 | 0.98 | C19—H192 | 0.96 |
C10—C19 | 1.544 (3) | C19—H193 | 0.96 |
C11—C12 | 1.535 (3) | | |
| | | |
O2—C1—C10 | 113.7 (2) | C12—C11—H112 | 108.92 (11) |
O2—C1—H11 | 108.82 (11) | H111—C11—H112 | 107.7 |
C10—C1—H11 | 108.82 (11) | C13—C12—C11 | 111.1 (2) |
O2—C1—H12 | 108.81 (12) | C13—C12—H121 | 109.41 (11) |
C10—C1—H12 | 108.81 (11) | C11—C12—H121 | 109.42 (12) |
H11—C1—H12 | 107.7 | C13—C12—H122 | 109.42 (10) |
C3—O2—C1 | 117.2 (2) | C11—C12—H122 | 109.41 (10) |
O3—C3—O2 | 118.7 (2) | H121—C12—H122 | 108.0 |
O3—C3—C4 | 123.0 (2) | C14—C13—C18 | 113.5 (2) |
O2—C3—C4 | 118.2 (2) | C14—C13—C12 | 107.67 (15) |
C5—C4—C3 | 122.3 (2) | C18—C13—C12 | 110.7 (2) |
C5—C4—H41 | 118.85 (12) | C14—C13—C17 | 98.85 (14) |
C3—C4—H41 | 118.85 (11) | C18—C13—C17 | 109.9 (2) |
C4—C5—C6 | 121.3 (2) | C12—C13—C17 | 115.9 (2) |
C4—C5—C10 | 120.0 (2) | C8—C14—C13 | 114.13 (14) |
C6—C5—C10 | 118.4 (2) | C8—C14—C15 | 118.9 (2) |
O6—C6—C5 | 109.9 (2) | C13—C14—C15 | 104.4 (2) |
O6—C6—C7 | 110.9 (2) | C8—C14—H141 | 106.16 (10) |
C5—C6—C7 | 112.5 (2) | C13—C14—H141 | 106.16 (10) |
O6—C6—H61 | 107.79 (12) | C15—C14—H141 | 106.16 (13) |
C5—C6—H61 | 107.79 (12) | C14—C15—C16 | 103.9 (2) |
C7—C6—H61 | 107.79 (12) | C14—C15—H151 | 110.98 (13) |
C6—O6—H6O | 102 (2) | C16—C15—H151 | 110.97 (13) |
C6—C7—C8 | 111.9 (2) | C14—C15—H152 | 110.98 (13) |
C6—C7—H71 | 109.24 (12) | C16—C15—H152 | 110.98 (14) |
C8—C7—H71 | 109.25 (11) | H151—C15—H152 | 109.0 |
C6—C7—H72 | 109.24 (10) | C17—C16—C15 | 105.50 (15) |
C8—C7—H72 | 109.24 (10) | C17—C16—H161 | 110.64 (12) |
H71—C7—H72 | 107.9 | C15—C16—H161 | 110.64 (14) |
C14—C8—C7 | 111.32 (15) | C17—C16—H162 | 110.64 (12) |
C14—C8—C9 | 108.67 (13) | C15—C16—H162 | 110.64 (13) |
C7—C8—C9 | 109.32 (14) | H161—C16—H162 | 108.8 |
C14—C8—H81 | 109.17 (10) | O17—C17—C16 | 114.7 (2) |
C7—C8—H81 | 109.17 (10) | O17—C17—C13 | 112.2 (2) |
C9—C8—H81 | 109.17 (10) | C16—C17—C13 | 104.5 (2) |
C11—C9—C8 | 112.93 (14) | O17—C17—H171 | 108.45 (11) |
C11—C9—C10 | 112.81 (14) | C16—C17—H171 | 108.44 (13) |
C8—C9—C10 | 111.50 (14) | C13—C17—H171 | 108.44 (10) |
C11—C9—H91 | 106.34 (11) | C17—O17—H17O | 107.3 (18) |
C8—C9—H91 | 106.34 (10) | C13—C18—H181 | 109.47 (11) |
C10—C9—H91 | 106.34 (9) | C13—C18—H182 | 109.47 (12) |
C5—C10—C1 | 107.1 (2) | H181—C18—H182 | 109.5 |
C5—C10—C19 | 108.1 (2) | C13—C18—H183 | 109.47 (12) |
C1—C10—C19 | 110.4 (2) | H181—C18—H183 | 109.5 |
C5—C10—C9 | 110.79 (14) | H182—C18—H183 | 109.5 |
C1—C10—C9 | 107.40 (15) | C10—C19—H191 | 109.47 (11) |
C19—C10—C9 | 112.9 (2) | C10—C19—H192 | 109.47 (12) |
C9—C11—C12 | 113.29 (15) | H191—C19—H192 | 109.5 |
C9—C11—H111 | 108.92 (11) | C10—C19—H193 | 109.47 (12) |
C12—C11—H111 | 108.92 (12) | H191—C19—H193 | 109.5 |
C9—C11—H112 | 108.91 (10) | H192—C19—H193 | 109.5 |
| | | |
C10—C1—O2—C3 | −47.7 (3) | C8—C9—C10—C1 | −166.7 (2) |
C1—O2—C3—O3 | −168.7 (2) | C11—C9—C10—C19 | −57.0 (2) |
C1—O2—C3—C4 | 14.2 (3) | C8—C9—C10—C19 | 71.4 (2) |
O3—C3—C4—C5 | −163.6 (2) | C8—C9—C11—C12 | 50.3 (2) |
O2—C3—C4—C5 | 13.3 (3) | C10—C9—C11—C12 | 177.9 (2) |
C3—C4—C5—C6 | 169.0 (2) | C9—C11—C12—C13 | −53.3 (2) |
C3—C4—C5—C10 | −5.6 (3) | C11—C12—C13—C14 | 56.5 (2) |
C4—C5—C6—O6 | 17.5 (3) | C11—C12—C13—C18 | −68.1 (2) |
C10—C5—C6—O6 | −167.9 (2) | C11—C12—C13—C17 | 166.0 (2) |
C4—C5—C6—C7 | 141.6 (2) | C7—C8—C14—C13 | 178.4 (2) |
C10—C5—C6—C7 | −43.7 (2) | C9—C8—C14—C13 | 58.0 (2) |
O6—C6—C7—C8 | 174.6 (2) | C7—C8—C14—C15 | −57.6 (2) |
C5—C6—C7—C8 | 51.0 (2) | C9—C8—C14—C15 | −178.0 (2) |
C6—C7—C8—C14 | −179.8 (2) | C18—C13—C14—C8 | 61.5 (2) |
C6—C7—C8—C9 | −59.7 (2) | C12—C13—C14—C8 | −61.4 (2) |
C14—C8—C9—C11 | −50.6 (2) | C17—C13—C14—C8 | 177.76 (15) |
C7—C8—C9—C11 | −172.3 (2) | C18—C13—C14—C15 | −70.0 (2) |
C14—C8—C9—C10 | −178.87 (14) | C12—C13—C14—C15 | 167.1 (2) |
C7—C8—C9—C10 | 59.5 (2) | C17—C13—C14—C15 | 46.3 (2) |
C4—C5—C10—C1 | −25.3 (2) | C8—C14—C15—C16 | −159.6 (2) |
C6—C5—C10—C1 | 159.9 (2) | C13—C14—C15—C16 | −31.0 (2) |
C4—C5—C10—C19 | 93.7 (2) | C14—C15—C16—C17 | 2.9 (3) |
C6—C5—C10—C19 | −81.1 (2) | C15—C16—C17—O17 | 149.2 (2) |
C4—C5—C10—C9 | −142.2 (2) | C15—C16—C17—C13 | 26.0 (2) |
C6—C5—C10—C9 | 43.1 (2) | C14—C13—C17—O17 | −168.9 (2) |
O2—C1—C10—C5 | 50.8 (2) | C18—C13—C17—O17 | −49.9 (2) |
O2—C1—C10—C19 | −66.7 (2) | C12—C13—C17—O17 | 76.4 (2) |
O2—C1—C10—C9 | 169.8 (2) | C14—C13—C17—C16 | −44.1 (2) |
C11—C9—C10—C5 | −178.4 (2) | C18—C13—C17—C16 | 74.9 (2) |
C8—C9—C10—C5 | −50.0 (2) | C12—C13—C17—C16 | −158.8 (2) |
C11—C9—C10—C1 | 65.0 (2) | | |
(22) 2-Oxa-4-androsten-3,17-dione and 2-Oxa-6beta-hydroxy-4-androsten-3,17-dione
top
Crystal data top
0.72(C18H24O4)·0.28(C18H24O4) | F(000) = 328 |
Mr = 304.37 | Dx = 1.271 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2y1 | Cell parameters from 58 reflections |
a = 6.2246 (7) Å | θ = 14.7–71.3° |
b = 12.014 (1) Å | µ = 0.72 mm−1 |
c = 10.915 (1) Å | T = 293 K |
β = 103.09 (1)° | Cubic, light brown |
V = 795.04 (13) Å3 | 0.35 × 0.30 × 0.30 mm |
Z = 2 | |
Data collection top
KM-4 diffractometer | Rint = 0.019 |
Radiation source: fine-focus sealed tube | θmax = 70.1°, θmin = 4.2° |
Graphite monochromator | h = 0→7 |
ω–2θ scans | k = 0→14 |
1651 measured reflections | l = −13→12 |
1542 independent reflections | 2 standard reflections every 100 reflections |
1497 reflections with I > 2σ(I) | intensity decay: less than 2.9% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | Calculated w = 1/[σ2(Fo2) + (0.0542P)2 + 0.0888P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.088 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.13 e Å−3 |
1542 reflections | Δρmin = −0.12 e Å−3 |
202 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0040 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.0 (3) |
Crystal data top
0.72(C18H24O4)·0.28(C18H24O4) | V = 795.04 (13) Å3 |
Mr = 304.37 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 6.2246 (7) Å | µ = 0.72 mm−1 |
b = 12.014 (1) Å | T = 293 K |
c = 10.915 (1) Å | 0.35 × 0.30 × 0.30 mm |
β = 103.09 (1)° | |
Data collection top
KM-4 diffractometer | Rint = 0.019 |
1651 measured reflections | 2 standard reflections every 100 reflections |
1542 independent reflections | intensity decay: less than 2.9% |
1497 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.088 | Δρmax = 0.13 e Å−3 |
S = 1.04 | Δρmin = −0.12 e Å−3 |
1542 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
202 parameters | Absolute structure parameter: 0.0 (3) |
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 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 | Occ. (<1) |
C1 | 0.2869 (5) | 0.2785 (2) | 0.2066 (2) | 0.0620 (6) | |
H11 | 0.3697 | 0.2816 | 0.1413 | 0.072* | |
H12 | 0.1336 | 0.2651 | 0.1662 | 0.070* | |
O2 | 0.3038 (3) | 0.38510 (13) | 0.26960 (18) | 0.0644 (5) | |
C3 | 0.2229 (4) | 0.39165 (19) | 0.3735 (2) | 0.0558 (5) | |
O3 | 0.1922 (3) | 0.48254 (15) | 0.4136 (2) | 0.0743 (6) | |
C4 | 0.1950 (3) | 0.28815 (19) | 0.4370 (2) | 0.0502 (5) | |
H4 | 0.1185 | 0.2896 | 0.5010 | 0.078* | |
C5 | 0.2737 (3) | 0.19166 (17) | 0.40767 (18) | 0.0413 (4) | |
C6 | 0.2868 (4) | 0.09080 (17) | 0.49156 (19) | 0.0473 (5) | |
H61 | 0.4443 | 0.0787 | 0.5272 | 0.063* | |
O6 | 0.1926 (4) | 0.1111 (2) | 0.5940 (2) | 0.0638 (9) | 0.721 (7) |
H6 | 0.096 (6) | 0.068 (3) | 0.5830 (7) | 0.069* | 0.721 (7) |
C7 | 0.2060 (4) | −0.01367 (18) | 0.4161 (2) | 0.0470 (5) | |
H71 | 0.0485 | −0.0079 | 0.3817 | 0.048* | |
H72 | 0.2320 | −0.0779 | 0.4713 | 0.065* | |
C8 | 0.3237 (3) | −0.03010 (16) | 0.30919 (17) | 0.0388 (4) | |
H8 | 0.4822 | −0.0388 | 0.3444 | 0.039* | |
C9 | 0.2854 (3) | 0.07209 (18) | 0.22164 (19) | 0.0423 (4) | |
H9 | 0.1251 | 0.0805 | 0.1939 | 0.041* | |
C10 | 0.3712 (3) | 0.18135 (17) | 0.29337 (18) | 0.0424 (4) | |
C11 | 0.3719 (5) | 0.0562 (2) | 0.1016 (2) | 0.0610 (6) | |
H111 | 0.3238 | 0.1185 | 0.0456 | 0.081* | |
H112 | 0.5319 | 0.0568 | 0.1239 | 0.068* | |
C12 | 0.2937 (5) | −0.0523 (2) | 0.0316 (2) | 0.0593 (6) | |
H121 | 0.1358 | −0.0490 | −0.0027 | 0.081* | |
H122 | 0.3660 | −0.0617 | −0.0377 | 0.079* | |
C13 | 0.3474 (3) | −0.14999 (18) | 0.12062 (19) | 0.0467 (5) | |
C14 | 0.2376 (3) | −0.13258 (16) | 0.23127 (18) | 0.0412 (4) | |
H14 | 0.0814 | −0.1181 | 0.1942 | 0.056* | |
C15 | 0.2468 (5) | −0.24719 (19) | 0.2939 (2) | 0.0578 (6) | |
H151 | 0.1363 | −0.2538 | 0.3434 | 0.083* | |
H152 | 0.3913 | −0.2613 | 0.3474 | 0.080* | |
C16 | 0.1982 (5) | −0.3268 (2) | 0.1807 (2) | 0.0700 (7) | |
H161 | 0.2894 | −0.3930 | 0.1982 | 0.110* | |
H162 | 0.0445 | −0.3491 | 0.1613 | 0.091* | |
C17 | 0.2517 (4) | −0.2622 (2) | 0.0725 (2) | 0.0525 (5) | |
O17 | 0.2187 (3) | −0.29409 (17) | −0.03526 (15) | 0.0701 (5) | |
C18 | 0.5984 (3) | −0.1708 (3) | 0.1623 (2) | 0.0665 (7) | |
H181 | 0.6694 | −0.1057 | 0.2037 | 0.114* | |
H182 | 0.6563 | −0.1870 | 0.0899 | 0.063* | |
H183 | 0.6254 | −0.2328 | 0.2192 | 0.113* | |
C19 | 0.6245 (3) | 0.1859 (2) | 0.3358 (2) | 0.0528 (5) | |
H191 | 0.6754 | 0.1261 | 0.3934 | 0.074* | |
H192 | 0.6682 | 0.2557 | 0.3766 | 0.072* | |
H193 | 0.6879 | 0.1787 | 0.2638 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0882 (18) | 0.0400 (12) | 0.0543 (12) | −0.0065 (11) | 0.0087 (12) | 0.0005 (10) |
O2 | 0.0866 (12) | 0.0359 (8) | 0.0709 (10) | −0.0039 (8) | 0.0183 (9) | 0.0046 (8) |
C3 | 0.0491 (10) | 0.0395 (12) | 0.0769 (15) | 0.0007 (9) | 0.0107 (10) | −0.0028 (11) |
O3 | 0.0765 (11) | 0.0393 (9) | 0.1103 (16) | 0.0057 (8) | 0.0281 (11) | −0.0072 (9) |
C4 | 0.0468 (11) | 0.0417 (11) | 0.0646 (13) | −0.0007 (8) | 0.0177 (9) | −0.0049 (10) |
C5 | 0.0387 (8) | 0.0371 (10) | 0.0475 (10) | −0.0045 (8) | 0.0084 (7) | −0.0036 (8) |
C6 | 0.0615 (12) | 0.0391 (11) | 0.0452 (10) | −0.0025 (9) | 0.0206 (9) | −0.0027 (9) |
O6 | 0.0859 (17) | 0.0559 (15) | 0.0602 (14) | −0.0234 (12) | 0.0385 (12) | −0.0170 (11) |
C7 | 0.0609 (11) | 0.0373 (10) | 0.0477 (11) | −0.0052 (9) | 0.0228 (9) | −0.0007 (9) |
C8 | 0.0417 (9) | 0.0362 (10) | 0.0389 (9) | −0.0008 (7) | 0.0097 (7) | −0.0003 (8) |
C9 | 0.0467 (10) | 0.0391 (10) | 0.0404 (9) | −0.0046 (8) | 0.0086 (7) | −0.0014 (8) |
C10 | 0.0480 (9) | 0.0368 (10) | 0.0431 (9) | −0.0048 (8) | 0.0119 (7) | 0.0005 (9) |
C11 | 0.0923 (17) | 0.0502 (13) | 0.0455 (11) | −0.0118 (13) | 0.0260 (11) | −0.0007 (10) |
C12 | 0.0829 (15) | 0.0553 (14) | 0.0408 (10) | −0.0067 (12) | 0.0164 (9) | −0.0054 (10) |
C13 | 0.0452 (10) | 0.0510 (12) | 0.0424 (10) | 0.0010 (9) | 0.0067 (8) | −0.0087 (9) |
C14 | 0.0405 (8) | 0.0385 (11) | 0.0445 (10) | −0.0008 (7) | 0.0092 (7) | −0.0019 (9) |
C15 | 0.0793 (15) | 0.0374 (12) | 0.0579 (12) | −0.0014 (10) | 0.0180 (11) | −0.0016 (10) |
C16 | 0.0945 (18) | 0.0412 (13) | 0.0738 (16) | −0.0032 (13) | 0.0181 (13) | −0.0070 (12) |
C17 | 0.0484 (10) | 0.0499 (12) | 0.0554 (11) | 0.0091 (9) | 0.0037 (8) | −0.0107 (10) |
O17 | 0.0773 (10) | 0.0695 (13) | 0.0588 (9) | 0.0043 (9) | 0.0056 (7) | −0.0259 (9) |
C18 | 0.0457 (11) | 0.0874 (19) | 0.0681 (14) | 0.0029 (12) | 0.0167 (10) | −0.0218 (14) |
C19 | 0.0491 (10) | 0.0544 (12) | 0.0584 (11) | −0.0132 (10) | 0.0192 (9) | −0.0109 (11) |
Geometric parameters (Å, º) top
C1—O2 | 1.446 (3) | C11—C12 | 1.534 (3) |
C1—C10 | 1.519 (3) | C11—H111 | 0.9700 |
C1—H11 | 0.9700 | C11—H112 | 0.9700 |
C1—H12 | 0.9700 | C12—C13 | 1.512 (3) |
O2—C3 | 1.344 (3) | C12—H121 | 0.9700 |
C3—O3 | 1.207 (3) | C12—H122 | 0.9700 |
C3—C4 | 1.453 (3) | C13—C17 | 1.519 (3) |
C4—C5 | 1.326 (3) | C13—C14 | 1.531 (3) |
C4—H4 | 0.9300 | C13—C18 | 1.545 (3) |
C5—C6 | 1.510 (3) | C14—C15 | 1.532 (3) |
C5—C10 | 1.511 (3) | C14—H14 | 0.9800 |
C6—O6 | 1.397 (3) | C15—C16 | 1.537 (3) |
C6—C7 | 1.523 (3) | C15—H151 | 0.9700 |
C6—H61 | 0.9800 | C15—H152 | 0.9700 |
O6—H6 | 0.7812 | C16—C17 | 1.511 (4) |
C7—C8 | 1.525 (2) | C16—H161 | 0.9700 |
C7—H71 | 0.9700 | C16—H162 | 0.9700 |
C7—H72 | 0.9700 | C17—O17 | 1.210 (3) |
C8—C14 | 1.523 (3) | C18—H181 | 0.9600 |
C8—C9 | 1.541 (3) | C18—H182 | 0.9600 |
C8—H8 | 0.9800 | C18—H183 | 0.9600 |
C9—C11 | 1.537 (3) | C19—H191 | 0.9600 |
C9—C10 | 1.559 (3) | C19—H192 | 0.9600 |
C9—H9 | 0.9800 | C19—H193 | 0.9600 |
C10—C19 | 1.540 (3) | | |
| | | |
O2—C1—C10 | 113.99 (18) | C9—C11—H111 | 108.9 |
O2—C1—H11 | 108.8 | C12—C11—H112 | 108.9 |
C10—C1—H11 | 108.8 | C9—C11—H112 | 108.9 |
O2—C1—H12 | 108.8 | H111—C11—H112 | 107.7 |
C10—C1—H12 | 108.8 | C13—C12—C11 | 109.88 (17) |
H11—C1—H12 | 107.6 | C13—C12—H121 | 109.7 |
C3—O2—C1 | 116.89 (18) | C11—C12—H121 | 109.7 |
O3—C3—O2 | 118.6 (2) | C13—C12—H122 | 109.7 |
O3—C3—C4 | 123.8 (2) | C11—C12—H122 | 109.7 |
O2—C3—C4 | 117.43 (19) | H121—C12—H122 | 108.2 |
C5—C4—C3 | 122.86 (19) | C12—C13—C17 | 117.04 (17) |
C5—C4—H4 | 118.6 | C12—C13—C14 | 109.14 (17) |
C3—C4—H4 | 118.6 | C17—C13—C14 | 100.58 (17) |
C4—C5—C6 | 121.83 (18) | C12—C13—C18 | 112.1 (2) |
C4—C5—C10 | 120.70 (18) | C17—C13—C18 | 104.44 (18) |
C6—C5—C10 | 117.29 (16) | C14—C13—C18 | 113.09 (16) |
O6—C6—C5 | 111.78 (19) | C8—C14—C13 | 112.79 (15) |
O6—C6—C7 | 115.46 (18) | C8—C14—C15 | 120.30 (16) |
C5—C6—C7 | 111.57 (17) | C13—C14—C15 | 104.50 (17) |
O6—C6—H61 | 105.7 | C8—C14—H14 | 106.1 |
C5—C6—H61 | 105.7 | C13—C14—H14 | 106.1 |
C7—C6—H61 | 105.7 | C15—C14—H14 | 106.1 |
C6—O6—H6 | 102.2 | C14—C15—C16 | 102.73 (18) |
C6—C7—C8 | 111.33 (16) | C14—C15—H151 | 111.2 |
C6—C7—H71 | 109.4 | C16—C15—H151 | 111.2 |
C8—C7—H71 | 109.4 | C14—C15—H152 | 111.2 |
C6—C7—H72 | 109.4 | C16—C15—H152 | 111.2 |
C8—C7—H72 | 109.4 | H151—C15—H152 | 109.1 |
H71—C7—H72 | 108.0 | C17—C16—C15 | 105.7 (2) |
C14—C8—C7 | 111.26 (16) | C17—C16—H161 | 110.6 |
C14—C8—C9 | 108.20 (14) | C15—C16—H161 | 110.6 |
C7—C8—C9 | 109.74 (16) | C17—C16—H162 | 110.6 |
C14—C8—H8 | 109.2 | C15—C16—H162 | 110.6 |
C7—C8—H8 | 109.2 | H161—C16—H162 | 108.7 |
C9—C8—H8 | 109.2 | O17—C17—C16 | 125.3 (2) |
C11—C9—C8 | 113.24 (17) | O17—C17—C13 | 125.7 (2) |
C11—C9—C10 | 112.72 (17) | C16—C17—C13 | 108.94 (18) |
C8—C9—C10 | 111.84 (15) | C13—C18—H181 | 109.5 |
C11—C9—H9 | 106.1 | C13—C18—H182 | 109.5 |
C8—C9—H9 | 106.1 | H181—C18—H182 | 109.5 |
C10—C9—H9 | 106.1 | C13—C18—H183 | 109.5 |
C5—C10—C1 | 107.75 (17) | H181—C18—H183 | 109.5 |
C5—C10—C19 | 108.92 (15) | H182—C18—H183 | 109.5 |
C1—C10—C19 | 110.22 (19) | C10—C19—H191 | 109.5 |
C5—C10—C9 | 109.12 (15) | C10—C19—H192 | 109.5 |
C1—C10—C9 | 107.63 (16) | H191—C19—H192 | 109.5 |
C19—C10—C9 | 113.06 (17) | C10—C19—H193 | 109.5 |
C12—C11—C9 | 113.45 (19) | H191—C19—H193 | 109.5 |
C12—C11—H111 | 108.9 | H192—C19—H193 | 109.5 |
Experimental details
| (10) | (11) | (12) | (13) |
Crystal data |
Chemical formula | C18H24O3 | C18H26O3 | C18H26O3 | C18H24O4 |
Mr | 288.37 | 290.39 | 290.39 | 304.37 |
Crystal system, space group | Monoclinic, P21 | Orthorhombic, P212121 | Orthorhombic, P212121 | Monoclinic, P21 |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 6.2321 (3), 9.9264 (6), 12.8120 (8) | 6.3180 (4), 6.4489 (5), 38.841 (3) | 14.241 (2), 9.4401 (9), 11.648 (2) | 6.2214 (7), 12.050 (1), 10.888 (1) |
α, β, γ (°) | 90, 97.079 (5), 90 | 90, 90, 90 | 90, 90, 90 | 90, 103.07 (1), 90 |
V (Å3) | 786.54 (8) | 1582.5 (2) | 1565.9 (4) | 795.10 (13) |
Z | 2 | 4 | 4 | 2 |
Radiation type | Cu Kα | Cu Kα | Cu Kα | Cu Kα |
µ (mm−1) | 0.65 | 0.64 | 0.65 | 0.72 |
Crystal size (mm) | 0.45 × 0.30 × 0.20 | 0.45 × 0.40 × 0.10 | 0.70 × 0.70 × 0.25 | 0.40 × 0.40 × 0.20 |
|
Data collection |
Diffractometer | KM-4 diffractometer | KM-4 diffractometer | KM-4 diffractometer | KM-4 diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1685, 1597, 1434 | 1736, 1736, 1567 | 1722, 1722, 1592 | 1624, 1596, 1458 |
Rint | 0.014 | 0.000 | 0.000 | 0.031 |
(sin θ/λ)max (Å−1) | 0.610 | 0.610 | 0.610 | 0.610 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.092, 1.06 | 0.031, 0.089, 1.05 | 0.031, 0.096, 1.07 | 0.036, 0.105, 1.07 |
No. of reflections | 1597 | 1736 | 1722 | 1512 |
No. of parameters | 190 | 219 | 222 | 228 |
No. of restraints | 1 | 0 | 0 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | Riding |
Δρmax, Δρmin (e Å−3) | 0.10, −0.13 | 0.16, −0.11 | 0.17, −0.10 | 0.14, −0.18 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.1 (3) | −0.2 (3) | −0.2 (3) | −0.03 (30) |
| (14) | (15) | (22) |
Crystal data |
Chemical formula | C18H26O4 | C18H26O4 | 0.72(C18H24O4)·0.28(C18H24O4) |
Mr | 306.39 | 306.39 | 304.37 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 | Monoclinic, P21 |
Temperature (K) | 293 | 293 | 293 |
a, b, c (Å) | 6.335 (1), 9.482 (1), 27.245 (6) | 9.3361 (7), 9.6261 (7), 17.764 (2) | 6.2246 (7), 12.014 (1), 10.915 (1) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 103.09 (1), 90 |
V (Å3) | 1636.6 (5) | 1596.5 (2) | 795.04 (13) |
Z | 4 | 4 | 2 |
Radiation type | Cu Kα | Cu Kα | Cu Kα |
µ (mm−1) | 0.70 | 0.71 | 0.72 |
Crystal size (mm) | 0.3 × 0.2 × 0.1 | 0.5 × 0.4 × 0.2 | 0.35 × 0.30 × 0.30 |
|
Data collection |
Diffractometer | KM-4 diffractometer | KM-4 diffractometer | KM-4 diffractometer |
Absorption correction | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1586, 1586, 913 | 1746, 1746, 1634 | 1651, 1542, 1497 |
Rint | 0.000 | 0.000 | 0.019 |
(sin θ/λ)max (Å−1) | 0.588 | 0.610 | 0.610 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.104, 0.98 | 0.031, 0.102, 1.06 | 0.032, 0.088, 1.04 |
No. of reflections | 1586 | 1741 | 1542 |
No. of parameters | 231 | 234 | 202 |
No. of restraints | 0 | 0 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | Riding | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.13 | 0.17, −0.11 | 0.13, −0.12 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.0 (5) | 0.06 (28) | 0.0 (3) |
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