Eplerenone [systematic name: 7α-(methoxycarbonyl)-3-oxo-9α,11-epoxy-17α-pregn-4-ene-21,17-carbolactone], an aldosterone receptor antagonist, crystallizes from ethanol as a monosolvate, C24H30O6·C2H6O. The eplerenone molecule has two five-membered rings, three six-membered rings and one three-membered ring. Both five-membered rings display envelope conformations, while the three six-membered rings assume envelope (cyclohexene), half-chair (cyclohexane sharing one edge with epoxy) and chair (other cyclohexane) conformations. The solvent molecule is disordered equally over two sites. It is linked to the eplerenone molecule by hydrogen bonds.
Supporting information
CCDC reference: 653034
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.056
- wR factor = 0.152
- Data-to-parameter ratio = 8.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C24 .. 3.00 Ang.
Alert level G
REFLT03_ALERT_4_G 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.
From the CIF: _diffrn_reflns_theta_max 25.20
From the CIF: _reflns_number_total 2559
Count of symmetry unique reflns 2564
Completeness (_total/calc) 99.80%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 ... S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 ... R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 ... R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 ... R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 ... R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 ... S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 ... S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 ... R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
10 ALERT level G = General alerts; check
9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
A microcrystalline powder sample of eplerenone was prepared in the manner
reported by Grob et al. (1997). Single crystals of the title
compound
were obtained from an ethanol solution of eplerenone.
The lattice ethanol molecule is disordered in the crystal structure; a two-site
model with each 0.5 site occupancies was adopted in the refinement. The C—C
and C—O distances for the disordered solvent molecule were constrained to
1.50±0.01 and 1.40±0.01 Å, respectively; atomic displacement parameters
for non-H atoms of the disordered solvent molecule were constrained to be the
same. Hydroxyl H atoms were placed in chemical sensible positions and refined
in riding mode with Uiso(H) = 1.5Ueq(O). Other H atoms were
placed in calculated positions with C—H = 0.93 to 0.98 Å, and refined in
riding mode with Uiso(H) = 1.5Ueq(C) for methyl or
1.2Ueq(C) for others. In the absence of significant anomalous
scattering effects, Friedel pairs were merged; the absolute configuration was
not determined.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
7
α-(methoxycarbonyl)-3-oxo-9
α,11-epoxy-17
α-pregn-4-ene-21,17-carbolactone
ethanol solvate
top
Crystal data top
C24H30O6·C2H6O | F(000) = 992 |
Mr = 460.55 | Dx = 1.228 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4788 reflections |
a = 8.3236 (5) Å | θ = 3.2–25.2° |
b = 12.8306 (9) Å | µ = 0.09 mm−1 |
c = 23.3173 (13) Å | T = 295 K |
V = 2490.2 (3) Å3 | Prism, colorless |
Z = 4 | 0.20 × 0.16 × 0.14 mm |
Data collection top
Rigaku R-AXIS RAPID IP diffractometer | 1955 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.054 |
Graphite monochromator | θmax = 25.2°, θmin = 3.0° |
ω scans | h = −9→8 |
19548 measured reflections | k = −15→15 |
2559 independent reflections | l = −27→27 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0933P)2 + 0.2684P] where P = (Fo2 + 2Fc2)/3 |
2559 reflections | (Δ/σ)max = 0.002 |
293 parameters | Δρmax = 0.30 e Å−3 |
6 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C24H30O6·C2H6O | V = 2490.2 (3) Å3 |
Mr = 460.55 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.3236 (5) Å | µ = 0.09 mm−1 |
b = 12.8306 (9) Å | T = 295 K |
c = 23.3173 (13) Å | 0.20 × 0.16 × 0.14 mm |
Data collection top
Rigaku R-AXIS RAPID IP diffractometer | 1955 reflections with I > 2σ(I) |
19548 measured reflections | Rint = 0.054 |
2559 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.056 | 6 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.30 e Å−3 |
2559 reflections | Δρmin = −0.19 e Å−3 |
293 parameters | |
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) |
O1 | −0.0903 (5) | 0.5823 (4) | 0.10016 (17) | 0.1137 (15) | |
O2 | 0.1457 (3) | 0.82438 (19) | 0.29175 (10) | 0.0474 (6) | |
O3 | 0.4884 (4) | 0.8328 (2) | 0.49749 (10) | 0.0644 (8) | |
O4 | 0.3946 (5) | 0.8951 (3) | 0.57892 (12) | 0.0842 (10) | |
O5 | 0.4856 (5) | 0.9197 (3) | 0.22555 (13) | 0.0866 (11) | |
O6 | 0.3136 (4) | 0.8354 (2) | 0.17081 (12) | 0.0691 (8) | |
C1 | −0.0244 (6) | 0.5948 (4) | 0.1464 (2) | 0.0742 (13) | |
C2 | 0.1457 (6) | 0.6130 (3) | 0.15092 (19) | 0.0642 (11) | |
H2 | 0.2062 | 0.6122 | 0.1174 | 0.077* | |
C3 | 0.2222 (5) | 0.6310 (3) | 0.20064 (16) | 0.0476 (9) | |
C4 | 0.1357 (4) | 0.6367 (3) | 0.25779 (16) | 0.0481 (9) | |
C5 | −0.0438 (4) | 0.6600 (4) | 0.2471 (2) | 0.0653 (11) | |
H5A | −0.1024 | 0.6499 | 0.2826 | 0.078* | |
H5B | −0.0552 | 0.7326 | 0.2361 | 0.078* | |
C6 | −0.1187 (6) | 0.5921 (4) | 0.2008 (2) | 0.0759 (13) | |
H6A | −0.1249 | 0.5208 | 0.2145 | 0.091* | |
H6B | −0.2272 | 0.6160 | 0.1933 | 0.091* | |
C7 | 0.4024 (4) | 0.6423 (3) | 0.20023 (16) | 0.0515 (9) | |
H7A | 0.4385 | 0.6512 | 0.1610 | 0.062* | |
H7B | 0.4502 | 0.5787 | 0.2149 | 0.062* | |
C8 | 0.4618 (4) | 0.7341 (3) | 0.23596 (14) | 0.0465 (9) | |
H8 | 0.5790 | 0.7285 | 0.2383 | 0.056* | |
C9 | 0.3961 (4) | 0.7217 (3) | 0.29729 (14) | 0.0432 (8) | |
H9 | 0.4299 | 0.6526 | 0.3105 | 0.052* | |
C10 | 0.2131 (4) | 0.7204 (3) | 0.29597 (15) | 0.0438 (8) | |
C11 | 0.1258 (4) | 0.7665 (3) | 0.34520 (16) | 0.0467 (9) | |
H11 | 0.0178 | 0.7384 | 0.3516 | 0.056* | |
C12 | 0.2055 (4) | 0.8119 (3) | 0.39783 (15) | 0.0508 (9) | |
H12A | 0.1525 | 0.7852 | 0.4318 | 0.061* | |
H12B | 0.1925 | 0.8871 | 0.3975 | 0.061* | |
C13 | 0.3852 (5) | 0.7856 (3) | 0.40082 (14) | 0.0474 (9) | |
C14 | 0.4600 (4) | 0.7996 (3) | 0.34071 (14) | 0.0451 (9) | |
H14 | 0.4309 | 0.8694 | 0.3271 | 0.054* | |
C15 | 0.6431 (5) | 0.7989 (4) | 0.35129 (17) | 0.0646 (12) | |
H15A | 0.6865 | 0.7293 | 0.3463 | 0.078* | |
H15B | 0.6972 | 0.8458 | 0.3250 | 0.078* | |
C16 | 0.6647 (5) | 0.8359 (5) | 0.41383 (17) | 0.0721 (13) | |
H16A | 0.7153 | 0.7820 | 0.4368 | 0.086* | |
H16B | 0.7307 | 0.8981 | 0.4153 | 0.086* | |
C17 | 0.4943 (5) | 0.8590 (3) | 0.43599 (14) | 0.0534 (10) | |
C18 | 0.4499 (5) | 0.9740 (3) | 0.43479 (17) | 0.0578 (10) | |
H18A | 0.3843 | 0.9900 | 0.4015 | 0.069* | |
H18B | 0.5455 | 1.0173 | 0.4339 | 0.069* | |
C19 | 0.3553 (7) | 0.9913 (4) | 0.49035 (16) | 0.0727 (13) | |
H19A | 0.3789 | 1.0590 | 0.5069 | 0.087* | |
H19B | 0.2406 | 0.9858 | 0.4837 | 0.087* | |
C20 | 0.4135 (6) | 0.9058 (3) | 0.52799 (16) | 0.0629 (11) | |
C21 | 0.1522 (6) | 0.5303 (3) | 0.28953 (19) | 0.0659 (11) | |
H21A | 0.2639 | 0.5144 | 0.2949 | 0.099* | |
H21B | 0.1027 | 0.4765 | 0.2671 | 0.099* | |
H21C | 0.1002 | 0.5346 | 0.3262 | 0.099* | |
C22 | 0.4032 (6) | 0.6722 (3) | 0.42265 (17) | 0.0648 (11) | |
H22A | 0.3698 | 0.6684 | 0.4620 | 0.097* | |
H22B | 0.5135 | 0.6511 | 0.4196 | 0.097* | |
H22C | 0.3374 | 0.6268 | 0.3999 | 0.097* | |
C23 | 0.4237 (5) | 0.8399 (3) | 0.21110 (15) | 0.0503 (9) | |
C24 | 0.2627 (8) | 0.9320 (4) | 0.1450 (2) | 0.0944 (18) | |
H24A | 0.2670 | 0.9867 | 0.1731 | 0.142* | |
H24B | 0.1546 | 0.9249 | 0.1312 | 0.142* | |
H24C | 0.3326 | 0.9489 | 0.1136 | 0.142* | |
O8 | 0.547 (6) | 0.823 (3) | 0.0144 (17) | 0.431 (13)* | 0.50 |
H8A | 0.5024 | 0.8527 | −0.0201 | 0.646* | 0.50 |
C81 | 0.715 (6) | 0.815 (6) | 0.021 (2) | 0.431 (13)* | 0.50 |
H81A | 0.7682 | 0.8468 | −0.0114 | 0.517* | 0.50 |
H81B | 0.7455 | 0.7423 | 0.0227 | 0.517* | 0.50 |
C82 | 0.769 (7) | 0.868 (5) | 0.075 (2) | 0.431 (13)* | 0.50 |
H82A | 0.8188 | 0.8181 | 0.1000 | 0.646* | 0.50 |
H82B | 0.6778 | 0.8983 | 0.0940 | 0.646* | 0.50 |
H82C | 0.8447 | 0.9219 | 0.0657 | 0.646* | 0.50 |
O9 | 0.632 (5) | 0.917 (4) | 0.0182 (15) | 0.431 (13)* | 0.50 |
H9A | 0.5650 | 0.9195 | −0.0163 | 0.646* | 0.50 |
C91 | 0.625 (7) | 0.824 (4) | 0.050 (3) | 0.431 (13)* | 0.50 |
H91A | 0.6519 | 0.7660 | 0.0249 | 0.517* | 0.50 |
H91B | 0.5155 | 0.8136 | 0.0632 | 0.517* | 0.50 |
C92 | 0.735 (7) | 0.825 (5) | 0.100 (2) | 0.431 (13)* | 0.50 |
H92A | 0.7614 | 0.7541 | 0.1100 | 0.646* | 0.50 |
H92B | 0.6839 | 0.8584 | 0.1315 | 0.646* | 0.50 |
H92C | 0.8316 | 0.8614 | 0.0898 | 0.646* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.100 (3) | 0.143 (4) | 0.098 (3) | −0.039 (3) | −0.033 (2) | −0.015 (3) |
O2 | 0.0473 (14) | 0.0399 (13) | 0.0551 (13) | 0.0060 (11) | 0.0018 (12) | 0.0004 (11) |
O3 | 0.091 (2) | 0.0635 (17) | 0.0388 (13) | 0.0233 (17) | −0.0092 (14) | −0.0007 (13) |
O4 | 0.127 (3) | 0.079 (2) | 0.0468 (16) | 0.021 (2) | 0.0019 (18) | 0.0003 (15) |
O5 | 0.114 (3) | 0.072 (2) | 0.0730 (19) | −0.039 (2) | −0.005 (2) | 0.0047 (17) |
O6 | 0.087 (2) | 0.0521 (17) | 0.0681 (16) | −0.0022 (17) | −0.0233 (16) | 0.0092 (14) |
C1 | 0.070 (3) | 0.068 (3) | 0.084 (3) | −0.016 (2) | −0.015 (3) | −0.018 (3) |
C2 | 0.070 (3) | 0.062 (3) | 0.061 (2) | −0.006 (2) | −0.003 (2) | −0.011 (2) |
C3 | 0.053 (2) | 0.0314 (18) | 0.058 (2) | 0.0005 (16) | 0.0028 (19) | −0.0040 (16) |
C4 | 0.0421 (18) | 0.041 (2) | 0.062 (2) | 0.0008 (16) | 0.0030 (18) | −0.0031 (16) |
C5 | 0.045 (2) | 0.060 (3) | 0.091 (3) | −0.001 (2) | −0.001 (2) | −0.023 (2) |
C6 | 0.053 (2) | 0.063 (3) | 0.112 (4) | −0.009 (2) | −0.008 (3) | −0.023 (3) |
C7 | 0.052 (2) | 0.054 (2) | 0.0484 (19) | 0.0091 (18) | 0.0050 (18) | −0.0047 (18) |
C8 | 0.0345 (18) | 0.061 (2) | 0.0443 (19) | 0.0012 (17) | 0.0017 (16) | −0.0036 (17) |
C9 | 0.0380 (17) | 0.047 (2) | 0.0443 (17) | 0.0067 (15) | 0.0050 (16) | 0.0000 (16) |
C10 | 0.0453 (18) | 0.0397 (19) | 0.0464 (18) | 0.0024 (16) | 0.0052 (17) | 0.0026 (16) |
C11 | 0.0408 (19) | 0.042 (2) | 0.057 (2) | 0.0010 (16) | 0.0100 (17) | 0.0014 (17) |
C12 | 0.054 (2) | 0.052 (2) | 0.0461 (18) | 0.0068 (19) | 0.0109 (18) | −0.0004 (17) |
C13 | 0.052 (2) | 0.052 (2) | 0.0380 (17) | 0.0077 (17) | 0.0021 (17) | −0.0009 (16) |
C14 | 0.0380 (18) | 0.058 (2) | 0.0397 (17) | 0.0012 (17) | 0.0022 (15) | 0.0004 (16) |
C15 | 0.045 (2) | 0.095 (4) | 0.054 (2) | 0.007 (2) | −0.0038 (19) | −0.012 (2) |
C16 | 0.053 (2) | 0.103 (4) | 0.060 (2) | 0.017 (3) | −0.010 (2) | −0.016 (3) |
C17 | 0.063 (2) | 0.060 (2) | 0.0365 (17) | 0.008 (2) | −0.0021 (17) | 0.0003 (17) |
C18 | 0.066 (3) | 0.056 (2) | 0.051 (2) | −0.001 (2) | −0.0043 (19) | 0.0061 (19) |
C19 | 0.105 (4) | 0.061 (3) | 0.052 (2) | 0.016 (3) | −0.004 (2) | 0.000 (2) |
C20 | 0.086 (3) | 0.059 (3) | 0.043 (2) | 0.010 (2) | −0.005 (2) | −0.0002 (19) |
C21 | 0.071 (3) | 0.048 (2) | 0.079 (3) | −0.001 (2) | 0.014 (2) | 0.005 (2) |
C22 | 0.088 (3) | 0.056 (2) | 0.051 (2) | 0.017 (2) | 0.004 (2) | 0.0080 (19) |
C23 | 0.053 (2) | 0.055 (2) | 0.0424 (18) | −0.0129 (19) | 0.0082 (17) | −0.0015 (17) |
C24 | 0.122 (5) | 0.071 (3) | 0.090 (3) | 0.020 (3) | −0.018 (3) | 0.018 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.221 (6) | C14—C15 | 1.545 (5) |
O2—C10 | 1.451 (4) | C14—H14 | 0.9800 |
O2—C11 | 1.460 (4) | C15—C16 | 1.544 (6) |
O3—C20 | 1.331 (5) | C15—H15A | 0.9700 |
O3—C17 | 1.474 (4) | C15—H15B | 0.9700 |
O4—C20 | 1.206 (5) | C16—C17 | 1.538 (6) |
O5—C23 | 1.195 (5) | C16—H16A | 0.9700 |
O6—C23 | 1.314 (5) | C16—H16B | 0.9700 |
O6—C24 | 1.441 (5) | C17—C18 | 1.522 (6) |
C1—C2 | 1.438 (7) | C18—C19 | 1.532 (6) |
C1—C6 | 1.492 (7) | C18—H18A | 0.9700 |
C2—C3 | 1.343 (6) | C18—H18B | 0.9700 |
C2—H2 | 0.9300 | C19—C20 | 1.486 (6) |
C3—C7 | 1.508 (5) | C19—H19A | 0.9700 |
C3—C4 | 1.516 (5) | C19—H19B | 0.9700 |
C4—C10 | 1.536 (5) | C21—H21A | 0.9600 |
C4—C5 | 1.544 (5) | C21—H21B | 0.9600 |
C4—C21 | 1.559 (5) | C21—H21C | 0.9600 |
C5—C6 | 1.520 (6) | C22—H22A | 0.9600 |
C5—H5A | 0.9700 | C22—H22B | 0.9600 |
C5—H5B | 0.9700 | C22—H22C | 0.9600 |
C6—H6A | 0.9700 | C24—H24A | 0.9600 |
C6—H6B | 0.9700 | C24—H24B | 0.9600 |
C7—C8 | 1.525 (5) | C24—H24C | 0.9600 |
C7—H7A | 0.9700 | O8—C81 | 1.409 (11) |
C7—H7B | 0.9700 | O8—H8A | 0.9668 |
C8—C23 | 1.510 (5) | C81—C82 | 1.494 (11) |
C8—C9 | 1.539 (5) | C81—H81A | 0.9700 |
C8—H8 | 0.9800 | C81—H81B | 0.9700 |
C9—C14 | 1.519 (5) | C82—H82A | 0.9600 |
C9—C10 | 1.523 (5) | C82—H82B | 0.9600 |
C9—H9 | 0.9800 | C82—H82C | 0.9600 |
C10—C11 | 1.482 (5) | O9—C91 | 1.403 (11) |
C11—C12 | 1.512 (5) | O9—H9A | 0.9804 |
C11—H11 | 0.9800 | C91—C92 | 1.483 (11) |
C12—C13 | 1.535 (5) | C91—H91A | 0.9700 |
C12—H12A | 0.9700 | C91—H91B | 0.9700 |
C12—H12B | 0.9700 | C92—H92A | 0.9600 |
C13—C14 | 1.544 (5) | C92—H92B | 0.9600 |
C13—C17 | 1.545 (6) | C92—H92C | 0.9600 |
C13—C22 | 1.548 (6) | | |
| | | |
C10—O2—C11 | 61.2 (2) | C14—C15—H15A | 110.7 |
C20—O3—C17 | 112.0 (3) | C16—C15—H15B | 110.7 |
C23—O6—C24 | 117.8 (4) | C14—C15—H15B | 110.7 |
O1—C1—C2 | 121.9 (5) | H15A—C15—H15B | 108.8 |
O1—C1—C6 | 120.8 (4) | C17—C16—C15 | 105.6 (3) |
C2—C1—C6 | 117.3 (4) | C17—C16—H16A | 110.6 |
C3—C2—C1 | 123.9 (4) | C15—C16—H16A | 110.6 |
C3—C2—H2 | 118.1 | C17—C16—H16B | 110.6 |
C1—C2—H2 | 118.1 | C15—C16—H16B | 110.6 |
C2—C3—C7 | 118.9 (4) | H16A—C16—H16B | 108.7 |
C2—C3—C4 | 122.8 (3) | O3—C17—C18 | 103.4 (3) |
C7—C3—C4 | 118.3 (3) | O3—C17—C16 | 108.3 (3) |
C3—C4—C10 | 110.1 (3) | C18—C17—C16 | 113.9 (4) |
C3—C4—C5 | 109.1 (3) | O3—C17—C13 | 111.0 (3) |
C10—C4—C5 | 111.4 (3) | C18—C17—C13 | 116.0 (3) |
C3—C4—C21 | 109.4 (3) | C16—C17—C13 | 104.3 (3) |
C10—C4—C21 | 107.4 (3) | C17—C18—C19 | 104.4 (3) |
C5—C4—C21 | 109.4 (3) | C17—C18—H18A | 110.9 |
C6—C5—C4 | 113.6 (3) | C19—C18—H18A | 110.9 |
C6—C5—H5A | 108.8 | C17—C18—H18B | 110.9 |
C4—C5—H5A | 108.8 | C19—C18—H18B | 110.9 |
C6—C5—H5B | 108.8 | H18A—C18—H18B | 108.9 |
C4—C5—H5B | 108.8 | C20—C19—C18 | 103.0 (4) |
H5A—C5—H5B | 107.7 | C20—C19—H19A | 111.2 |
C1—C6—C5 | 112.0 (4) | C18—C19—H19A | 111.2 |
C1—C6—H6A | 109.2 | C20—C19—H19B | 111.2 |
C5—C6—H6A | 109.2 | C18—C19—H19B | 111.2 |
C1—C6—H6B | 109.2 | H19A—C19—H19B | 109.1 |
C5—C6—H6B | 109.2 | O4—C20—O3 | 120.5 (4) |
H6A—C6—H6B | 107.9 | O4—C20—C19 | 128.5 (4) |
C3—C7—C8 | 113.1 (3) | O3—C20—C19 | 110.9 (3) |
C3—C7—H7A | 109.0 | C4—C21—H21A | 109.5 |
C8—C7—H7A | 109.0 | C4—C21—H21B | 109.5 |
C3—C7—H7B | 109.0 | H21A—C21—H21B | 109.5 |
C8—C7—H7B | 109.0 | C4—C21—H21C | 109.5 |
H7A—C7—H7B | 107.8 | H21A—C21—H21C | 109.5 |
C23—C8—C7 | 114.6 (3) | H21B—C21—H21C | 109.5 |
C23—C8—C9 | 112.0 (3) | C13—C22—H22A | 109.5 |
C7—C8—C9 | 108.2 (3) | C13—C22—H22B | 109.5 |
C23—C8—H8 | 107.2 | H22A—C22—H22B | 109.5 |
C7—C8—H8 | 107.2 | C13—C22—H22C | 109.5 |
C9—C8—H8 | 107.2 | H22A—C22—H22C | 109.5 |
C14—C9—C10 | 111.8 (3) | H22B—C22—H22C | 109.5 |
C14—C9—C8 | 115.3 (3) | O5—C23—O6 | 122.7 (4) |
C10—C9—C8 | 109.7 (3) | O5—C23—C8 | 124.9 (4) |
C14—C9—H9 | 106.5 | O6—C23—C8 | 112.4 (3) |
C10—C9—H9 | 106.5 | O6—C24—H24A | 109.5 |
C8—C9—H9 | 106.5 | O6—C24—H24B | 109.5 |
O2—C10—C11 | 59.7 (2) | H24A—C24—H24B | 109.5 |
O2—C10—C9 | 112.2 (3) | O6—C24—H24C | 109.5 |
C11—C10—C9 | 118.1 (3) | H24A—C24—H24C | 109.5 |
O2—C10—C4 | 116.2 (3) | H24B—C24—H24C | 109.5 |
C11—C10—C4 | 121.5 (3) | C81—O8—H8A | 120.4 |
C9—C10—C4 | 116.0 (3) | C81—O8—H9A | 91.0 |
O2—C11—C10 | 59.1 (2) | O8—C81—C82 | 111.1 (11) |
O2—C11—C12 | 116.5 (3) | O8—C81—H81A | 109.4 |
C10—C11—C12 | 124.6 (3) | C82—C81—H81A | 109.4 |
O2—C11—H11 | 114.9 | O8—C81—H81B | 109.4 |
C10—C11—H11 | 114.9 | C82—C81—H81B | 109.4 |
C12—C11—H11 | 114.9 | H81A—C81—H81B | 108.0 |
C11—C12—C13 | 112.3 (3) | C81—C82—H82A | 109.5 |
C11—C12—H12A | 109.1 | C81—C82—H82B | 109.5 |
C13—C12—H12A | 109.1 | H82A—C82—H82B | 109.5 |
C11—C12—H12B | 109.1 | C81—C82—H82C | 109.5 |
C13—C12—H12B | 109.1 | H82A—C82—H82C | 109.5 |
H12A—C12—H12B | 107.9 | H82B—C82—H82C | 109.5 |
C12—C13—C14 | 109.0 (3) | C91—O9—H9A | 115.6 |
C12—C13—C17 | 117.6 (3) | O9—C91—C92 | 112.3 (12) |
C14—C13—C17 | 100.0 (3) | O9—C91—H91A | 109.1 |
C12—C13—C22 | 108.5 (3) | C92—C91—H91A | 109.1 |
C14—C13—C22 | 111.7 (3) | O9—C91—H91B | 109.1 |
C17—C13—C22 | 110.0 (3) | C92—C91—H91B | 109.1 |
C9—C14—C13 | 112.8 (3) | H91A—C91—H91B | 107.9 |
C9—C14—C15 | 116.6 (3) | C91—C92—H92A | 109.5 |
C13—C14—C15 | 104.6 (3) | C91—C92—H92B | 109.5 |
C9—C14—H14 | 107.5 | H92A—C92—H92B | 109.5 |
C13—C14—H14 | 107.5 | C91—C92—H92C | 109.5 |
C15—C14—H14 | 107.5 | H92A—C92—H92C | 109.5 |
C16—C15—C14 | 105.3 (3) | H92B—C92—H92C | 109.5 |
C16—C15—H15A | 110.7 | | |
| | | |
O1—C1—C2—C3 | 177.4 (5) | O2—C11—C12—C13 | −81.0 (4) |
C6—C1—C2—C3 | −2.3 (7) | C10—C11—C12—C13 | −11.7 (5) |
C1—C2—C3—C7 | 176.2 (4) | C11—C12—C13—C14 | 43.1 (4) |
C1—C2—C3—C4 | −1.5 (7) | C11—C12—C13—C17 | 155.9 (3) |
C2—C3—C4—C10 | −143.4 (4) | C11—C12—C13—C22 | −78.6 (4) |
C7—C3—C4—C10 | 38.9 (4) | C10—C9—C14—C13 | 51.8 (4) |
C2—C3—C4—C5 | −20.9 (5) | C8—C9—C14—C13 | 178.0 (3) |
C7—C3—C4—C5 | 161.4 (3) | C10—C9—C14—C15 | 172.9 (3) |
C2—C3—C4—C21 | 98.7 (4) | C8—C9—C14—C15 | −60.9 (5) |
C7—C3—C4—C21 | −79.0 (4) | C12—C13—C14—C9 | −66.2 (4) |
C3—C4—C5—C6 | 47.3 (5) | C17—C13—C14—C9 | 169.9 (3) |
C10—C4—C5—C6 | 169.0 (4) | C22—C13—C14—C9 | 53.7 (4) |
C21—C4—C5—C6 | −72.4 (5) | C12—C13—C14—C15 | 166.1 (3) |
O1—C1—C6—C5 | −150.7 (5) | C17—C13—C14—C15 | 42.2 (4) |
C2—C1—C6—C5 | 29.0 (7) | C22—C13—C14—C15 | −74.1 (4) |
C4—C5—C6—C1 | −52.5 (6) | C9—C14—C15—C16 | −151.0 (4) |
C2—C3—C7—C8 | 134.9 (4) | C13—C14—C15—C16 | −25.7 (5) |
C4—C3—C7—C8 | −47.3 (5) | C14—C15—C16—C17 | −1.4 (5) |
C3—C7—C8—C23 | −70.2 (4) | C20—O3—C17—C18 | 14.6 (5) |
C3—C7—C8—C9 | 55.7 (4) | C20—O3—C17—C16 | 135.7 (4) |
C23—C8—C9—C14 | −59.7 (4) | C20—O3—C17—C13 | −110.5 (4) |
C7—C8—C9—C14 | 172.9 (3) | C15—C16—C17—O3 | 146.3 (4) |
C23—C8—C9—C10 | 67.5 (4) | C15—C16—C17—C18 | −99.4 (4) |
C7—C8—C9—C10 | −59.9 (4) | C15—C16—C17—C13 | 28.0 (5) |
C11—O2—C10—C9 | −110.5 (3) | C12—C13—C17—O3 | 82.8 (4) |
C11—O2—C10—C4 | 112.7 (4) | C14—C13—C17—O3 | −159.5 (3) |
C14—C9—C10—O2 | 48.9 (4) | C22—C13—C17—O3 | −41.9 (4) |
C8—C9—C10—O2 | −80.2 (4) | C12—C13—C17—C18 | −34.7 (5) |
C14—C9—C10—C11 | −17.5 (5) | C14—C13—C17—C18 | 83.0 (4) |
C8—C9—C10—C11 | −146.7 (3) | C22—C13—C17—C18 | −159.5 (3) |
C14—C9—C10—C4 | −174.2 (3) | C12—C13—C17—C16 | −160.8 (3) |
C8—C9—C10—C4 | 56.6 (4) | C14—C13—C17—C16 | −43.1 (4) |
C3—C4—C10—O2 | 91.2 (4) | C22—C13—C17—C16 | 74.5 (4) |
C5—C4—C10—O2 | −30.0 (5) | O3—C17—C18—C19 | −23.4 (4) |
C21—C4—C10—O2 | −149.7 (3) | C16—C17—C18—C19 | −140.6 (4) |
C3—C4—C10—C11 | 160.2 (3) | C13—C17—C18—C19 | 98.3 (4) |
C5—C4—C10—C11 | 39.1 (5) | C17—C18—C19—C20 | 23.9 (5) |
C21—C4—C10—C11 | −80.7 (4) | C17—O3—C20—O4 | 178.1 (4) |
C3—C4—C10—C9 | −44.0 (4) | C17—O3—C20—C19 | 1.0 (5) |
C5—C4—C10—C9 | −165.1 (3) | C18—C19—C20—O4 | 167.2 (5) |
C21—C4—C10—C9 | 75.1 (4) | C18—C19—C20—O3 | −16.1 (5) |
C10—O2—C11—C12 | 116.1 (3) | C24—O6—C23—O5 | −2.4 (6) |
C9—C10—C11—O2 | 100.7 (3) | C24—O6—C23—C8 | 177.9 (4) |
C4—C10—C11—O2 | −104.0 (3) | C7—C8—C23—O5 | −164.2 (4) |
O2—C10—C11—C12 | −102.7 (4) | C9—C8—C23—O5 | 72.0 (5) |
C9—C10—C11—C12 | −2.0 (5) | C7—C8—C23—O6 | 15.5 (4) |
C4—C10—C11—C12 | 153.4 (3) | C9—C8—C23—O6 | −108.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8A···O1i | 0.96 | 2.19 | 3.15 (4) | 178 |
O9—H9A···O1i | 0.98 | 2.34 | 3.32 (4) | 177 |
C6—H6A···O2ii | 0.97 | 2.53 | 3.447 (6) | 157 |
C7—H7B···O5iii | 0.97 | 2.52 | 3.467 (5) | 164 |
C11—H11···O4iv | 0.98 | 2.57 | 3.337 (5) | 135 |
C14—H14···O5 | 0.98 | 2.50 | 3.103 (5) | 120 |
C21—H21A···O5iii | 0.96 | 2.46 | 3.351 (6) | 154 |
C92—H92A···O1v | 0.96 | 2.54 | 3.44 (6) | 155 |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x, y−1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1/2, −y+3/2, −z+1; (v) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | C24H30O6·C2H6O |
Mr | 460.55 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 295 |
a, b, c (Å) | 8.3236 (5), 12.8306 (9), 23.3173 (13) |
V (Å3) | 2490.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.20 × 0.16 × 0.14 |
|
Data collection |
Diffractometer | Rigaku R-AXIS RAPID IP diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19548, 2559, 1955 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.599 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.151, 1.05 |
No. of reflections | 2559 |
No. of parameters | 293 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.19 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8A···O1i | 0.96 | 2.19 | 3.15 (4) | 178 |
O9—H9A···O1i | 0.98 | 2.34 | 3.32 (4) | 177 |
Symmetry code: (i) x+1/2, −y+3/2, −z. |
The eplerenone is known as an aldosterone receptor antagonist and can be administered in a therapeutically effective amount where use of an aldosterone receptor antagonist (Grob et al., 1985). The crystal structure of the eplerenone ethanol solvate is reported here.
The crystal of the title compound consists of eplerenone molecules and lattice ethanol molecules (Fig. 1). The molecule of eplerenone contains three six-membered rings, two five-membered rings and one three-membered ring. A ring analysis (Spek, 2003) indicates that three six-membered rings assume different conformations: chair, half-chair and envelope; both five-membered rings display the similar envelope configuration. This agrees with those found in the structure of eplerenone THF solvate (Yang et al. 2007) and in the structure of eplerenone dioxane solvate (Xu et al., 2007). The C2—C3 bond distance of 1.343 (6) Å indicates the typical C?C double bond. The C23-ester group forms an intra-molecular C—H···O hydrogen bond with the adjacent C14-methine group (Table 1). This structural feature is also found in the crystal structure of eplerenone dichloromethane solvate (Grob et al., 1997).
In the crystal structure, lattice solvent molecules are disorderly located in the cavities formed by eplerenone molecules and link with eplerenone molecules via O—H···O and C—H···O hydrogen bonding (Table 1).