Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703944X/hk2310sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703944X/hk2310Isup2.hkl |
CCDC reference: 663705
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.010 Å
- R factor = 0.078
- wR factor = 0.199
- Data-to-parameter ratio = 9.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.72 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.45 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10
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 25.98 From the CIF: _reflns_number_total 2189 Count of symmetry unique reflns 2191 Completeness (_total/calc) 99.91% 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 C7 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 62
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Mohr & Nickisch (2005); Kelly & Sykes (1968). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).
The title compound, (I), was prepared by a literature method (Kelly & Sykes, 1968). The crystals were obtained by dissolving (I) (1.0 g, 2.5 mmol) in methanol (50 ml), and evaporating the solvent slowly at room temperature for about 15 d.
H atoms were positioned geometrically, with C—H = 0.93, 0.98, 0.96 and 0.97 Å for aromatic, methine, methyl and methylene H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 methyl H, and x = 1.2 for all other H atoms.
The title compound, (I), is an intermediate product of drospirenone, which is a new oral contraceptive (Mohr & Nickisch, 2005). We report herein its crystal structure.
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987).
Rings A (C4—C9), B (C7/C8/C10—C13) and C (C10/C11/C14—C17) are not planar, having total puckering amplitudes, QT, of 0.547 (3), 0.477 (2) and 0.676 (3) Å, respectively, and chair, flattened boat and chair conformations, respectively [φ = -173.98 (3)°, θ = 169.83 (3)°; φ = -16.01 (2)°, θ = 115.71 (3)° and φ = -147.03 (3)°, θ = 86.92 (3)°, respectively] (Cremer & Pople, 1975). Rings D (C16/C17/C19—C21) and E (O3/O4/C19/C24/C25) have envelope conformations with atoms C16 and C19 displaced by 0.646 (3) Å and 0.220 (2) Å from the planes of the other four ring atoms, respectively. Rings D and E have pseudo twofold axis and pseudo mirror plane, respectively, running through atom C20 and midpoint of C16—C17 bond (for ring D) and atom C19 and midpoint of C24—C25 bond (for ring E), as can be deduced from the torsion angles (Table 1).
The intramolecular C—H···O hydrogen bonds (Table 2, Fig. 1) result in the formation of three more five-membered rings F (O1/O2/C3/C4/H4A), G (C15/C16/C19/O4/H15A) and H (O3/C16/C19/C23/H23B), in which they may be effective in the stabilization of the structure.
As can be seen from the packing diagram (Fig. 2), the molecules of (I) are elongated along the c axis, and stacked along the a axis. Dipole-dipole and van der Waals interactions may be effective in the molecular packing.
For related literature, see: Mohr & Nickisch (2005); Kelly & Sykes (1968). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C23H34O4 | F(000) = 816 |
Mr = 374.50 | Dx = 1.207 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 25 reflections |
a = 10.197 (2) Å | θ = 9–12° |
b = 7.5370 (15) Å | µ = 0.08 mm−1 |
c = 27.143 (5) Å | T = 298 K |
β = 99.04 (3)° | Block, colorless |
V = 2060.2 (7) Å3 | 0.40 × 0.30 × 0.10 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1420 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.065 |
Graphite monochromator | θmax = 26.0°, θmin = 1.5° |
ω/2θ scans | h = −12→12 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→9 |
Tmin = 0.976, Tmax = 0.990 | l = 0→33 |
2324 measured reflections | 3 standard reflections every 120 min |
2189 independent reflections | intensity decay: none |
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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.06P)2 + 5P] where P = (Fo2 + 2Fc2)/3 |
2189 reflections | (Δ/σ)max = 0.012 |
227 parameters | Δρmax = 0.48 e Å−3 |
62 restraints | Δρmin = −0.33 e Å−3 |
C23H34O4 | V = 2060.2 (7) Å3 |
Mr = 374.50 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 10.197 (2) Å | µ = 0.08 mm−1 |
b = 7.5370 (15) Å | T = 298 K |
c = 27.143 (5) Å | 0.40 × 0.30 × 0.10 mm |
β = 99.04 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1420 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.065 |
Tmin = 0.976, Tmax = 0.990 | 3 standard reflections every 120 min |
2324 measured reflections | intensity decay: none |
2189 independent reflections |
R[F2 > 2σ(F2)] = 0.078 | 62 restraints |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.48 e Å−3 |
2189 reflections | Δρmin = −0.33 e Å−3 |
227 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.1505 (5) | −0.0998 (10) | 0.05652 (17) | 0.095 (2) | |
O2 | −0.3488 (7) | −0.0028 (10) | 0.0652 (2) | 0.109 | |
O3 | 0.3844 (5) | 0.0504 (10) | 0.44585 (17) | 0.0851 (18) | |
O4 | 0.1664 (4) | 0.1086 (8) | 0.42607 (16) | 0.0675 (14) | |
C2 | −0.3092 (10) | −0.0908 (17) | −0.0154 (3) | 0.108 | |
H2A | −0.2345 | −0.0601 | −0.0312 | 0.162* | |
H2B | −0.3834 | −0.0169 | −0.0282 | 0.162* | |
H2C | −0.3321 | −0.2129 | −0.0220 | 0.162* | |
C3 | −0.2745 (8) | −0.0634 (13) | 0.0394 (3) | 0.078 (2) | |
C4 | −0.1026 (7) | −0.0719 (15) | 0.1084 (2) | 0.078 (3) | |
H4A | −0.1720 | −0.0156 | 0.1242 | 0.094* | |
C5 | −0.0628 (8) | −0.2437 (12) | 0.1339 (2) | 0.069 (2) | |
H5A | 0.0052 | −0.2996 | 0.1179 | 0.083* | |
H5B | −0.1389 | −0.3225 | 0.1304 | 0.083* | |
C6 | −0.0101 (7) | −0.2169 (11) | 0.1891 (2) | 0.0611 (19) | |
H6A | 0.0189 | −0.3306 | 0.2036 | 0.073* | |
H6B | −0.0822 | −0.1754 | 0.2055 | 0.073* | |
C7 | 0.1070 (6) | −0.0832 (10) | 0.1997 (2) | 0.0470 (16) | |
C8 | 0.0725 (6) | 0.0808 (9) | 0.1667 (2) | 0.0465 (15) | |
C9 | 0.0181 (7) | 0.0490 (11) | 0.1131 (2) | 0.0637 (19) | |
H9A | 0.0859 | −0.0052 | 0.0966 | 0.076* | |
H9B | −0.0067 | 0.1613 | 0.0968 | 0.076* | |
C10 | 0.1242 (5) | −0.0273 (8) | 0.2554 (2) | 0.0393 (13) | |
H10A | 0.0351 | −0.0008 | 0.2627 | 0.047* | |
C11 | 0.2064 (6) | 0.1409 (9) | 0.2669 (2) | 0.0449 (15) | |
H11A | 0.2946 | 0.1220 | 0.2579 | 0.054* | |
C12 | 0.1398 (6) | 0.2947 (10) | 0.2366 (2) | 0.0528 (16) | |
H12A | 0.0666 | 0.3378 | 0.2521 | 0.063* | |
H12B | 0.2031 | 0.3907 | 0.2366 | 0.063* | |
C13 | 0.0893 (6) | 0.2431 (10) | 0.1843 (2) | 0.0538 (17) | |
H13A | 0.0671 | 0.3350 | 0.1616 | 0.065* | |
C14 | 0.1793 (7) | −0.1834 (10) | 0.2906 (2) | 0.0566 (18) | |
H14A | 0.1186 | −0.2830 | 0.2848 | 0.068* | |
H14B | 0.2640 | −0.2211 | 0.2822 | 0.068* | |
C15 | 0.1978 (7) | −0.1332 (10) | 0.3463 (2) | 0.0550 (17) | |
H15A | 0.1117 | −0.1110 | 0.3560 | 0.066* | |
H15B | 0.2387 | −0.2314 | 0.3661 | 0.066* | |
C16 | 0.2849 (6) | 0.0321 (9) | 0.3568 (2) | 0.0473 (15) | |
C17 | 0.2215 (5) | 0.1801 (8) | 0.3228 (2) | 0.0434 (14) | |
H17A | 0.1308 | 0.1918 | 0.3301 | 0.052* | |
C19 | 0.2886 (6) | 0.1226 (11) | 0.4089 (3) | 0.0588 (17) | |
C20 | 0.3178 (8) | 0.3188 (13) | 0.3994 (3) | 0.076 (2) | |
H20A | 0.4092 | 0.3464 | 0.4131 | 0.092* | |
H20B | 0.2602 | 0.3943 | 0.4154 | 0.092* | |
C21 | 0.2937 (7) | 0.3518 (11) | 0.3427 (3) | 0.0630 (19) | |
H21A | 0.2385 | 0.4555 | 0.3342 | 0.076* | |
H21B | 0.3767 | 0.3664 | 0.3299 | 0.076* | |
C22 | 0.2318 (6) | −0.1720 (12) | 0.1853 (2) | 0.066 (2) | |
H22A | 0.2554 | −0.2731 | 0.2063 | 0.099* | |
H22B | 0.3039 | −0.0886 | 0.1894 | 0.099* | |
H22C | 0.2137 | −0.2094 | 0.1511 | 0.099* | |
C23 | 0.4290 (6) | −0.0059 (12) | 0.3500 (3) | 0.068 (2) | |
H23A | 0.4298 | −0.0641 | 0.3186 | 0.102* | |
H23B | 0.4702 | −0.0810 | 0.3766 | 0.102* | |
H23C | 0.4771 | 0.1038 | 0.3506 | 0.102* | |
C24 | 0.1802 (8) | −0.0145 (15) | 0.4659 (3) | 0.088 (3) | |
H24A | 0.1344 | −0.1244 | 0.4556 | 0.105* | |
H24B | 0.1445 | 0.0336 | 0.4942 | 0.105* | |
C25 | 0.3240 (9) | −0.0442 (17) | 0.4786 (4) | 0.103 | |
H25B | 0.3553 | −0.0051 | 0.5125 | 0.123* | |
H25A | 0.3440 | −0.1694 | 0.4763 | 0.123* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.080 (4) | 0.156 (6) | 0.043 (3) | 0.023 (4) | −0.014 (2) | −0.027 (4) |
O2 | 0.109 | 0.109 | 0.109 | 0.000 | 0.017 | 0.000 |
O3 | 0.056 (2) | 0.141 (5) | 0.052 (3) | 0.003 (3) | −0.012 (2) | 0.003 (3) |
O4 | 0.057 (2) | 0.104 (4) | 0.044 (2) | 0.006 (3) | 0.0146 (19) | −0.004 (3) |
C2 | 0.108 | 0.108 | 0.108 | 0.000 | 0.017 | 0.000 |
C3 | 0.069 (4) | 0.100 (6) | 0.056 (4) | 0.010 (4) | −0.020 (3) | 0.000 (4) |
C4 | 0.063 (4) | 0.132 (8) | 0.037 (4) | 0.015 (5) | 0.000 (3) | −0.015 (5) |
C5 | 0.075 (5) | 0.087 (6) | 0.047 (4) | −0.024 (5) | 0.012 (3) | −0.026 (4) |
C6 | 0.064 (4) | 0.067 (5) | 0.052 (4) | −0.010 (4) | 0.009 (3) | −0.018 (4) |
C7 | 0.043 (3) | 0.069 (4) | 0.030 (3) | 0.003 (3) | 0.009 (2) | 0.002 (3) |
C8 | 0.047 (3) | 0.058 (4) | 0.035 (3) | 0.000 (3) | 0.008 (2) | −0.003 (3) |
C9 | 0.074 (5) | 0.072 (5) | 0.045 (4) | −0.003 (4) | 0.007 (3) | −0.004 (4) |
C10 | 0.038 (3) | 0.047 (3) | 0.035 (3) | 0.002 (3) | 0.009 (2) | −0.004 (3) |
C11 | 0.037 (3) | 0.066 (4) | 0.033 (3) | 0.001 (3) | 0.010 (2) | −0.004 (3) |
C12 | 0.054 (4) | 0.060 (4) | 0.045 (4) | 0.001 (3) | 0.011 (3) | −0.001 (3) |
C13 | 0.054 (4) | 0.066 (5) | 0.041 (4) | 0.006 (4) | 0.005 (3) | 0.011 (3) |
C14 | 0.064 (4) | 0.058 (4) | 0.046 (4) | −0.008 (4) | 0.004 (3) | 0.006 (3) |
C15 | 0.062 (4) | 0.052 (4) | 0.051 (4) | −0.004 (3) | 0.007 (3) | 0.010 (3) |
C16 | 0.046 (3) | 0.057 (4) | 0.038 (3) | 0.001 (3) | 0.005 (3) | −0.003 (3) |
C17 | 0.033 (3) | 0.050 (4) | 0.047 (3) | 0.003 (3) | 0.008 (2) | 0.000 (3) |
C19 | 0.045 (3) | 0.076 (5) | 0.056 (4) | 0.001 (3) | 0.007 (3) | −0.003 (3) |
C20 | 0.075 (5) | 0.094 (7) | 0.058 (4) | −0.014 (5) | 0.002 (4) | −0.027 (5) |
C21 | 0.060 (4) | 0.065 (5) | 0.062 (4) | −0.009 (4) | 0.005 (3) | −0.007 (4) |
C22 | 0.065 (4) | 0.090 (6) | 0.045 (4) | 0.022 (4) | 0.013 (3) | −0.001 (4) |
C23 | 0.044 (3) | 0.095 (6) | 0.065 (4) | 0.005 (4) | 0.011 (3) | 0.001 (4) |
C24 | 0.080 (4) | 0.117 (6) | 0.067 (4) | −0.015 (5) | 0.014 (4) | 0.008 (4) |
C25 | 0.103 | 0.103 | 0.103 | 0.000 | 0.016 | 0.000 |
O1—C3 | 1.307 (8) | C12—C13 | 1.483 (9) |
O1—C4 | 1.432 (7) | C12—H12A | 0.9700 |
O4—C19 | 1.402 (8) | C12—H12B | 0.9700 |
O4—C24 | 1.414 (10) | C13—H13A | 0.9300 |
O3—C25 | 1.361 (11) | C14—C15 | 1.540 (8) |
O3—C19 | 1.396 (8) | C14—H14A | 0.9700 |
O2—C3 | 1.201 (10) | C14—H14B | 0.9700 |
C2—C3 | 1.487 (11) | C15—C16 | 1.530 (9) |
C2—H2A | 0.9600 | C15—H15A | 0.9700 |
C2—H2B | 0.9600 | C15—H15B | 0.9700 |
C2—H2C | 0.9600 | C16—C17 | 1.526 (9) |
C4—C5 | 1.494 (13) | C16—C23 | 1.537 (8) |
C4—C9 | 1.521 (11) | C16—C19 | 1.564 (9) |
C4—H4A | 0.9800 | C17—C21 | 1.544 (10) |
C5—C6 | 1.523 (9) | C17—H17A | 0.9800 |
C5—H5A | 0.9700 | C19—C20 | 1.538 (12) |
C5—H5B | 0.9700 | C20—C21 | 1.539 (10) |
C6—C7 | 1.555 (9) | C20—H20A | 0.9700 |
C6—H6A | 0.9700 | C20—H20B | 0.9700 |
C6—H6B | 0.9700 | C21—H21A | 0.9700 |
C7—C8 | 1.535 (9) | C21—H21B | 0.9700 |
C7—C22 | 1.542 (8) | C22—H22A | 0.9600 |
C7—C10 | 1.552 (7) | C22—H22B | 0.9600 |
C8—C13 | 1.314 (10) | C22—H22C | 0.9600 |
C8—C9 | 1.494 (8) | C23—H23A | 0.9600 |
C9—H9A | 0.9700 | C23—H23B | 0.9600 |
C9—H9B | 0.9700 | C23—H23C | 0.9600 |
C10—C11 | 1.525 (8) | C24—C25 | 1.470 (11) |
C10—C14 | 1.563 (9) | C24—H24A | 0.9700 |
C10—H10A | 0.9800 | C24—H24B | 0.9700 |
C11—C12 | 1.519 (9) | C25—H25B | 0.9700 |
C11—C17 | 1.528 (8) | C25—H25A | 0.9700 |
C11—H11A | 0.9800 | ||
C3—O1—C4 | 118.7 (6) | C15—C14—C10 | 113.0 (6) |
C19—O4—C24 | 108.5 (6) | C15—C14—H14A | 109.0 |
C25—O3—C19 | 109.7 (6) | C10—C14—H14A | 109.0 |
C3—C2—H2A | 109.5 | C15—C14—H14B | 109.0 |
C3—C2—H2B | 109.5 | C10—C14—H14B | 109.0 |
H2A—C2—H2B | 109.5 | H14A—C14—H14B | 107.8 |
C3—C2—H2C | 109.5 | C16—C15—C14 | 111.2 (5) |
H2A—C2—H2C | 109.5 | C16—C15—H15A | 109.4 |
H2B—C2—H2C | 109.5 | C14—C15—H15A | 109.4 |
O2—C3—O1 | 122.4 (7) | C16—C15—H15B | 109.4 |
O2—C3—C2 | 124.4 (8) | C14—C15—H15B | 109.4 |
O1—C3—C2 | 113.1 (8) | H15A—C15—H15B | 108.0 |
O1—C4—C5 | 110.7 (8) | C15—C16—C17 | 107.7 (5) |
O1—C4—C9 | 108.5 (7) | C15—C16—C23 | 111.3 (6) |
C5—C4—C9 | 108.9 (6) | C17—C16—C23 | 112.7 (5) |
O1—C4—H4A | 109.6 | C15—C16—C19 | 117.1 (5) |
C5—C4—H4A | 109.6 | C17—C16—C19 | 100.2 (5) |
C9—C4—H4A | 109.6 | C23—C16—C19 | 107.6 (5) |
C4—C5—C6 | 111.7 (7) | C16—C17—C11 | 115.3 (5) |
C4—C5—H5A | 109.3 | C16—C17—C21 | 105.5 (5) |
C6—C5—H5A | 109.3 | C11—C17—C21 | 118.6 (5) |
C4—C5—H5B | 109.3 | C16—C17—H17A | 105.5 |
C6—C5—H5B | 109.3 | C11—C17—H17A | 105.5 |
H5A—C5—H5B | 108.0 | C21—C17—H17A | 105.5 |
C5—C6—C7 | 114.3 (6) | O3—C19—O4 | 106.8 (6) |
C5—C6—H6A | 108.7 | O3—C19—C20 | 111.3 (7) |
C7—C6—H6A | 108.7 | O4—C19—C20 | 109.5 (6) |
C5—C6—H6B | 108.7 | O3—C19—C16 | 113.2 (6) |
C7—C6—H6B | 108.7 | O4—C19—C16 | 111.8 (5) |
H6A—C6—H6B | 107.6 | C20—C19—C16 | 104.2 (6) |
C8—C7—C22 | 108.9 (5) | C19—C20—C21 | 108.6 (6) |
C8—C7—C10 | 109.3 (5) | C19—C20—H20A | 110.0 |
C22—C7—C10 | 113.2 (5) | C21—C20—H20A | 110.0 |
C8—C7—C6 | 108.4 (5) | C19—C20—H20B | 110.0 |
C22—C7—C6 | 108.2 (6) | C21—C20—H20B | 110.0 |
C10—C7—C6 | 108.9 (5) | H20A—C20—H20B | 108.4 |
C13—C8—C9 | 120.7 (6) | C17—C21—C20 | 102.0 (6) |
C13—C8—C7 | 122.2 (5) | C17—C21—H21A | 111.4 |
C9—C8—C7 | 117.1 (6) | C20—C21—H21A | 111.4 |
C8—C9—C4 | 110.4 (5) | C17—C21—H21B | 111.4 |
C8—C9—H9A | 109.6 | C20—C21—H21B | 111.4 |
C4—C9—H9A | 109.6 | H21A—C21—H21B | 109.2 |
C8—C9—H9B | 109.6 | C7—C22—H22A | 109.5 |
C4—C9—H9B | 109.6 | C7—C22—H22B | 109.5 |
H9A—C9—H9B | 108.1 | H22A—C22—H22B | 109.5 |
C11—C10—C7 | 113.6 (5) | C7—C22—H22C | 109.5 |
C11—C10—C14 | 111.5 (4) | H22A—C22—H22C | 109.5 |
C7—C10—C14 | 111.4 (5) | H22B—C22—H22C | 109.5 |
C11—C10—H10A | 106.6 | C16—C23—H23A | 109.5 |
C7—C10—H10A | 106.6 | C16—C23—H23B | 109.5 |
C14—C10—H10A | 106.6 | H23A—C23—H23B | 109.5 |
C12—C11—C10 | 109.8 (5) | C16—C23—H23C | 109.5 |
C12—C11—C17 | 111.0 (5) | H23A—C23—H23C | 109.5 |
C10—C11—C17 | 109.3 (5) | H23B—C23—H23C | 109.5 |
C12—C11—H11A | 108.9 | O4—C24—C25 | 104.8 (7) |
C10—C11—H11A | 108.9 | O4—C24—H24A | 110.8 |
C17—C11—H11A | 108.9 | C25—C24—H24A | 110.8 |
C13—C12—C11 | 112.2 (6) | O4—C24—H24B | 110.8 |
C13—C12—H12A | 109.2 | C25—C24—H24B | 110.8 |
C11—C12—H12A | 109.2 | H24A—C24—H24B | 108.9 |
C13—C12—H12B | 109.2 | O3—C25—C24 | 107.7 (8) |
C11—C12—H12B | 109.2 | O3—C25—H25B | 110.2 |
H12A—C12—H12B | 107.9 | C24—C25—H25B | 110.2 |
C8—C13—C12 | 126.6 (6) | O3—C25—H25A | 110.2 |
C8—C13—H13A | 116.7 | C24—C25—H25A | 110.2 |
C12—C13—H13A | 116.7 | H25B—C25—H25A | 108.5 |
C4—O1—C3—O2 | 2.1 (15) | C14—C15—C16—C17 | 55.8 (7) |
C4—O1—C3—C2 | 177.4 (10) | C14—C15—C16—C23 | −68.2 (7) |
C3—O1—C4—C5 | 115.6 (9) | C14—C15—C16—C19 | 167.5 (6) |
C3—O1—C4—C9 | −125.0 (9) | C15—C16—C17—C11 | −59.4 (7) |
O1—C4—C5—C6 | 179.4 (5) | C23—C16—C17—C11 | 63.7 (7) |
C9—C4—C5—C6 | 60.2 (8) | C19—C16—C17—C11 | 177.7 (5) |
C4—C5—C6—C7 | −55.3 (9) | C15—C16—C17—C21 | 167.8 (5) |
C5—C6—C7—C8 | 45.2 (8) | C23—C16—C17—C21 | −69.1 (7) |
C5—C6—C7—C22 | −72.6 (8) | C19—C16—C17—C21 | 44.9 (6) |
C5—C6—C7—C10 | 163.9 (6) | C12—C11—C17—C16 | 178.8 (5) |
C22—C7—C8—C13 | −108.8 (7) | C10—C11—C17—C16 | 57.6 (6) |
C10—C7—C8—C13 | 15.3 (8) | C12—C11—C17—C21 | −54.8 (7) |
C6—C7—C8—C13 | 133.7 (7) | C10—C11—C17—C21 | −176.1 (5) |
C22—C7—C8—C9 | 71.3 (7) | C25—O3—C19—O4 | 14.6 (9) |
C10—C7—C8—C9 | −164.6 (5) | C25—O3—C19—C20 | 134.1 (8) |
C6—C7—C8—C9 | −46.1 (7) | C25—O3—C19—C16 | −108.9 (8) |
C13—C8—C9—C4 | −125.4 (8) | C24—O4—C19—O3 | −16.4 (8) |
C7—C8—C9—C4 | 54.4 (8) | C24—O4—C19—C20 | −137.0 (7) |
O1—C4—C9—C8 | −179.5 (6) | C24—O4—C19—C16 | 108.0 (7) |
C5—C4—C9—C8 | −58.9 (8) | C15—C16—C19—O3 | 87.0 (7) |
C8—C7—C10—C11 | −44.8 (6) | C17—C16—C19—O3 | −157.0 (6) |
C22—C7—C10—C11 | 76.7 (7) | C23—C16—C19—O3 | −39.1 (8) |
C6—C7—C10—C11 | −163.0 (5) | C15—C16—C19—O4 | −33.7 (8) |
C8—C7—C10—C14 | −171.8 (5) | C17—C16—C19—O4 | 82.3 (7) |
C22—C7—C10—C14 | −50.3 (7) | C23—C16—C19—O4 | −159.9 (6) |
C6—C7—C10—C14 | 70.1 (7) | C15—C16—C19—C20 | −151.9 (6) |
C7—C10—C11—C12 | 60.1 (6) | C17—C16—C19—C20 | −35.9 (6) |
C14—C10—C11—C12 | −172.9 (5) | C23—C16—C19—C20 | 82.0 (7) |
C7—C10—C11—C17 | −177.9 (5) | O3—C19—C20—C21 | 137.3 (6) |
C14—C10—C11—C17 | −51.0 (6) | O4—C19—C20—C21 | −104.8 (6) |
C10—C11—C12—C13 | −42.8 (7) | C16—C19—C20—C21 | 15.0 (8) |
C17—C11—C12—C13 | −163.8 (5) | C16—C17—C21—C20 | −35.8 (7) |
C9—C8—C13—C12 | 178.9 (6) | C11—C17—C21—C20 | −166.7 (6) |
C7—C8—C13—C12 | −0.9 (10) | C19—C20—C21—C17 | 12.0 (8) |
C11—C12—C13—C8 | 15.1 (10) | C19—O4—C24—C25 | 11.9 (9) |
C11—C10—C14—C15 | 51.9 (7) | C19—O3—C25—C24 | −7.1 (11) |
C7—C10—C14—C15 | 180.0 (5) | O4—C24—C25—O3 | −3.0 (11) |
C10—C14—C15—C16 | −54.5 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O2 | 0.98 | 2.22 | 2.650 (10) | 105 |
C15—H15A···O4 | 0.97 | 2.52 | 2.886 (8) | 102 |
C23—H23B···O3 | 0.96 | 2.41 | 2.744 (9) | 100 |
Experimental details
Crystal data | |
Chemical formula | C23H34O4 |
Mr | 374.50 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 298 |
a, b, c (Å) | 10.197 (2), 7.5370 (15), 27.143 (5) |
β (°) | 99.04 (3) |
V (Å3) | 2060.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.30 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.976, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2324, 2189, 1420 |
Rint | 0.065 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.078, 0.199, 1.04 |
No. of reflections | 2189 |
No. of parameters | 227 |
No. of restraints | 62 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.33 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
O3—C19—O4 | 106.8 (6) | O4—C19—C16 | 111.8 (5) |
O3—C19—C20 | 111.3 (7) | O4—C24—C25 | 104.8 (7) |
O4—C19—C20 | 109.5 (6) | O3—C25—C24 | 107.7 (8) |
O3—C19—C16 | 113.2 (6) | ||
C19—C16—C17—C21 | 44.9 (6) | C16—C17—C21—C20 | −35.8 (7) |
C25—O3—C19—O4 | 14.6 (9) | C19—C20—C21—C17 | 12.0 (8) |
C24—O4—C19—O3 | −16.4 (8) | C19—O4—C24—C25 | 11.9 (9) |
C17—C16—C19—C20 | −35.9 (6) | C19—O3—C25—C24 | −7.1 (11) |
C16—C19—C20—C21 | 15.0 (8) | O4—C24—C25—O3 | −3.0 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O2 | 0.98 | 2.22 | 2.650 (10) | 105.0 |
C15—H15A···O4 | 0.97 | 2.52 | 2.886 (8) | 102.0 |
C23—H23B···O3 | 0.96 | 2.41 | 2.744 (9) | 100.0 |
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The title compound, (I), is an intermediate product of drospirenone, which is a new oral contraceptive (Mohr & Nickisch, 2005). We report herein its crystal structure.
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987).
Rings A (C4—C9), B (C7/C8/C10—C13) and C (C10/C11/C14—C17) are not planar, having total puckering amplitudes, QT, of 0.547 (3), 0.477 (2) and 0.676 (3) Å, respectively, and chair, flattened boat and chair conformations, respectively [φ = -173.98 (3)°, θ = 169.83 (3)°; φ = -16.01 (2)°, θ = 115.71 (3)° and φ = -147.03 (3)°, θ = 86.92 (3)°, respectively] (Cremer & Pople, 1975). Rings D (C16/C17/C19—C21) and E (O3/O4/C19/C24/C25) have envelope conformations with atoms C16 and C19 displaced by 0.646 (3) Å and 0.220 (2) Å from the planes of the other four ring atoms, respectively. Rings D and E have pseudo twofold axis and pseudo mirror plane, respectively, running through atom C20 and midpoint of C16—C17 bond (for ring D) and atom C19 and midpoint of C24—C25 bond (for ring E), as can be deduced from the torsion angles (Table 1).
The intramolecular C—H···O hydrogen bonds (Table 2, Fig. 1) result in the formation of three more five-membered rings F (O1/O2/C3/C4/H4A), G (C15/C16/C19/O4/H15A) and H (O3/C16/C19/C23/H23B), in which they may be effective in the stabilization of the structure.
As can be seen from the packing diagram (Fig. 2), the molecules of (I) are elongated along the c axis, and stacked along the a axis. Dipole-dipole and van der Waals interactions may be effective in the molecular packing.