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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052336/cv2322sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052336/cv2322Isup2.hkl |
CCDC reference: 667449
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.099
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
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 27.49 From the CIF: _reflns_number_total 2539 Count of symmetry unique reflns 2552 Completeness (_total/calc) 99.49% 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 C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . 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 C15 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 10 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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
The title compound was obtained by biotransformation with Colletotrichum lini from dehydroepiandrosterone(DHEA) according to the literature method (Andrea et al., 2006). Dehydroepiandrosterone(DHEA) was kindly offered by Mr. Pan, Jiubang Chemistry Corp. Ltd., Shanghai, China. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation from the mixture of tetrahydrofuran and H2O (9:1).
C-bound H atoms were placed in calculated positions (C—H 0.96–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq of the parent atom. The hydroxy H atoms were located in a difference map and refined isotropically with restaint O—H=0.84 (2) Å. The H atoms in H2O molecules were located in a difference map and refined isotropically with restaints O—H= 0.83 (2) Å. Due to the absence of any significantanomalous scatterers in the compound, 1937 Friedel pairs were merged before the final refinement.
Drospirenone is a new contraceptive drug with the special antimineralocorticoid and antiandrogenic properties (Muhn et al., 1995). The title compound, (I), as a key starting material for the synthesis of drospirenone, was obtained by biotransformation with Colletotrichum lini from dehydroepiandrosterone (DHEA) (Romano et al., 2006). We report here the crystal structure of (I).
In (I) (Fig. 1), ring A assumes a slightly twisty chair conformation and ring C takes a regular chair conformation. In ring B, atoms C8 and C9 deviate at 0.242 and -0.503 Å from the mean plane C5—C7/C10, respectively, thus ring B takes a half-chair conformation. Ring D has a somewhat twisty envelope conformation: atoms C13, C15, C16 and C17 are nearly coplanar and atom C14 deviates from their mean plane at 0.625 Å.
In the crystal (Fig. 2), the crystalline water molecules involved in the formation of hydrogen bonding. The intermolecular and intramolecular O—H···O hydrogen bonding are found in the crystal lattice (Table 1).
For related literature, see: Andrea et al. (2006); Muhn et al. (1995).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
C19H28O4·2H2O | F(000) = 776 |
Mr = 356.45 | Dx = 1.227 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4751 reflections |
a = 6.0653 (8) Å | θ = 2.3–25.8° |
b = 12.4906 (16) Å | µ = 0.09 mm−1 |
c = 25.472 (3) Å | T = 296 K |
V = 1929.8 (4) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.30 × 0.20 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 2539 independent reflections |
Radiation source: fine-focus sealed tube | 2289 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −7→7 |
Tmin = 0.975, Tmax = 0.983 | k = −16→12 |
12301 measured reflections | l = −33→32 |
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)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0532P)2 + 0.2939P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2539 reflections | Δρmax = 0.20 e Å−3 |
256 parameters | Δρmin = −0.21 e Å−3 |
7 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.015 (2) |
C19H28O4·2H2O | V = 1929.8 (4) Å3 |
Mr = 356.45 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.0653 (8) Å | µ = 0.09 mm−1 |
b = 12.4906 (16) Å | T = 296 K |
c = 25.472 (3) Å | 0.40 × 0.30 × 0.20 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 2539 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 2289 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.983 | Rint = 0.026 |
12301 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 7 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.20 e Å−3 |
2539 reflections | Δρmin = −0.21 e Å−3 |
256 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 | 0.8995 (3) | 0.83766 (13) | 0.94606 (5) | 0.0479 (4) | |
H1X | 0.994 (5) | 0.884 (2) | 0.9523 (11) | 0.083 (11)* | |
O2 | 1.0556 (3) | 0.96442 (12) | 0.69625 (6) | 0.0464 (4) | |
H2X | 1.048 (5) | 0.9884 (19) | 0.6657 (7) | 0.060 (8)* | |
O3 | 0.8912 (4) | 1.01700 (14) | 0.59879 (6) | 0.0725 (6) | |
H3X | 0.904 (5) | 1.054 (2) | 0.5714 (8) | 0.076 (9)* | |
O4 | 0.7005 (4) | 0.68704 (14) | 0.53143 (6) | 0.0679 (5) | |
O5 | 0.0560 (3) | 0.64593 (14) | 0.98689 (6) | 0.0547 (4) | |
H5X | 0.027 (6) | 0.7099 (16) | 0.9776 (11) | 0.078 (9)* | |
H5Y | 0.166 (4) | 0.657 (2) | 1.0062 (10) | 0.076 (10)* | |
O6 | 1.2334 (5) | 0.9667 (2) | 0.96135 (14) | 0.1160 (11) | |
H6X | 1.325 (7) | 0.937 (4) | 0.9813 (17) | 0.174* | |
H6Y | 1.258 (8) | 1.0295 (17) | 0.9615 (16) | 0.129 (16)* | |
C1 | 0.7195 (4) | 0.71106 (15) | 0.81999 (8) | 0.0434 (5) | |
H1A | 0.6202 | 0.6519 | 0.8131 | 0.052* | |
H1B | 0.8654 | 0.6896 | 0.8085 | 0.052* | |
C2 | 0.7263 (4) | 0.73072 (17) | 0.87909 (8) | 0.0457 (5) | |
H2A | 0.5794 | 0.7468 | 0.8919 | 0.055* | |
H2B | 0.7791 | 0.6671 | 0.8970 | 0.055* | |
C3 | 0.8782 (3) | 0.82337 (16) | 0.89005 (7) | 0.0401 (4) | |
H3 | 1.0238 | 0.8074 | 0.8753 | 0.048* | |
C4 | 0.7891 (4) | 0.92309 (16) | 0.86418 (7) | 0.0437 (5) | |
H4A | 0.8881 | 0.9825 | 0.8710 | 0.052* | |
H4B | 0.6467 | 0.9405 | 0.8793 | 0.052* | |
C5 | 0.7647 (3) | 0.90839 (14) | 0.80534 (7) | 0.0353 (4) | |
C6 | 0.8447 (4) | 0.98109 (14) | 0.77263 (7) | 0.0395 (4) | |
H6 | 0.9146 | 1.0401 | 0.7874 | 0.047* | |
C7 | 0.8322 (3) | 0.97645 (14) | 0.71421 (7) | 0.0370 (4) | |
H7 | 0.7756 | 1.0451 | 0.7014 | 0.044* | |
C8 | 0.6798 (3) | 0.88707 (14) | 0.69432 (7) | 0.0338 (4) | |
H8 | 0.5267 | 0.9116 | 0.6970 | 0.041* | |
C9 | 0.7080 (3) | 0.78640 (13) | 0.72853 (7) | 0.0332 (4) | |
H9 | 0.8660 | 0.7701 | 0.7284 | 0.040* | |
C10 | 0.6452 (3) | 0.80810 (14) | 0.78689 (7) | 0.0348 (4) | |
C11 | 0.5923 (4) | 0.68699 (16) | 0.70619 (8) | 0.0505 (5) | |
H11A | 0.6357 | 0.6250 | 0.7266 | 0.061* | |
H11B | 0.4342 | 0.6957 | 0.7101 | 0.061* | |
C12 | 0.6449 (4) | 0.66589 (17) | 0.64823 (8) | 0.0512 (6) | |
H12A | 0.7997 | 0.6478 | 0.6445 | 0.061* | |
H12B | 0.5582 | 0.6058 | 0.6357 | 0.061* | |
C13 | 0.5931 (4) | 0.76454 (16) | 0.61572 (8) | 0.0415 (5) | |
C14 | 0.7281 (3) | 0.85949 (15) | 0.63714 (7) | 0.0349 (4) | |
H14 | 0.8819 | 0.8354 | 0.6367 | 0.042* | |
C15 | 0.7121 (4) | 0.94462 (17) | 0.59409 (8) | 0.0465 (5) | |
H15 | 0.5715 | 0.9830 | 0.5965 | 0.056* | |
C16 | 0.7217 (5) | 0.87818 (19) | 0.54340 (8) | 0.0547 (6) | |
H16A | 0.6131 | 0.9035 | 0.5184 | 0.066* | |
H16B | 0.8667 | 0.8831 | 0.5275 | 0.066* | |
C17 | 0.6729 (4) | 0.76470 (18) | 0.55922 (8) | 0.0470 (5) | |
C18 | 0.3422 (4) | 0.7862 (2) | 0.61283 (10) | 0.0593 (6) | |
H18A | 0.2878 | 0.8033 | 0.6472 | 0.089* | |
H18B | 0.2683 | 0.7236 | 0.5999 | 0.089* | |
H18C | 0.3149 | 0.8452 | 0.5896 | 0.089* | |
C19 | 0.3950 (4) | 0.8263 (2) | 0.79409 (9) | 0.0526 (6) | |
H19A | 0.3456 | 0.8802 | 0.7700 | 0.079* | |
H19B | 0.3662 | 0.8492 | 0.8294 | 0.079* | |
H19C | 0.3177 | 0.7606 | 0.7874 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0535 (9) | 0.0549 (9) | 0.0352 (7) | −0.0040 (8) | −0.0004 (7) | 0.0027 (6) |
O2 | 0.0432 (8) | 0.0525 (8) | 0.0436 (7) | −0.0128 (7) | −0.0001 (7) | 0.0049 (7) |
O3 | 0.1036 (16) | 0.0654 (10) | 0.0484 (9) | −0.0366 (11) | −0.0181 (10) | 0.0222 (8) |
O4 | 0.0860 (14) | 0.0634 (10) | 0.0543 (9) | 0.0029 (11) | 0.0013 (10) | −0.0193 (8) |
O5 | 0.0672 (12) | 0.0499 (9) | 0.0471 (8) | 0.0059 (9) | −0.0137 (8) | −0.0068 (7) |
O6 | 0.0978 (19) | 0.0640 (14) | 0.186 (3) | −0.0229 (14) | −0.069 (2) | 0.0263 (16) |
C1 | 0.0507 (12) | 0.0330 (9) | 0.0465 (10) | −0.0046 (9) | −0.0029 (10) | 0.0049 (8) |
C2 | 0.0508 (12) | 0.0432 (11) | 0.0430 (10) | −0.0027 (10) | −0.0013 (10) | 0.0105 (8) |
C3 | 0.0392 (10) | 0.0455 (10) | 0.0355 (9) | 0.0018 (9) | 0.0035 (8) | 0.0009 (8) |
C4 | 0.0549 (12) | 0.0363 (9) | 0.0399 (9) | 0.0032 (9) | 0.0030 (10) | −0.0026 (8) |
C5 | 0.0380 (10) | 0.0296 (8) | 0.0383 (8) | 0.0062 (8) | 0.0009 (8) | −0.0011 (7) |
C6 | 0.0502 (11) | 0.0277 (8) | 0.0408 (9) | −0.0020 (8) | −0.0053 (9) | −0.0021 (7) |
C7 | 0.0437 (10) | 0.0253 (8) | 0.0420 (9) | −0.0008 (8) | −0.0021 (8) | 0.0047 (7) |
C8 | 0.0306 (9) | 0.0316 (8) | 0.0390 (8) | 0.0019 (8) | −0.0012 (8) | 0.0002 (7) |
C9 | 0.0312 (9) | 0.0295 (8) | 0.0388 (9) | −0.0017 (7) | 0.0011 (7) | 0.0008 (7) |
C10 | 0.0314 (9) | 0.0331 (9) | 0.0399 (9) | 0.0001 (7) | 0.0023 (8) | 0.0030 (7) |
C11 | 0.0635 (15) | 0.0381 (10) | 0.0498 (11) | −0.0165 (11) | 0.0010 (11) | −0.0010 (9) |
C12 | 0.0637 (15) | 0.0365 (10) | 0.0532 (11) | −0.0110 (10) | −0.0012 (11) | −0.0089 (9) |
C13 | 0.0363 (10) | 0.0434 (10) | 0.0446 (10) | −0.0041 (9) | −0.0019 (9) | −0.0080 (8) |
C14 | 0.0322 (9) | 0.0351 (9) | 0.0374 (8) | −0.0001 (8) | −0.0017 (8) | 0.0005 (7) |
C15 | 0.0548 (13) | 0.0439 (11) | 0.0409 (10) | −0.0010 (10) | −0.0081 (10) | 0.0043 (8) |
C16 | 0.0642 (15) | 0.0610 (13) | 0.0389 (10) | 0.0004 (13) | −0.0021 (11) | −0.0008 (10) |
C17 | 0.0408 (11) | 0.0556 (12) | 0.0447 (10) | 0.0025 (10) | −0.0063 (9) | −0.0101 (9) |
C18 | 0.0360 (11) | 0.0793 (17) | 0.0624 (13) | −0.0065 (12) | −0.0042 (10) | −0.0115 (13) |
C19 | 0.0328 (10) | 0.0746 (15) | 0.0504 (12) | −0.0008 (11) | 0.0051 (9) | 0.0034 (11) |
O1—C3 | 1.443 (2) | C8—C14 | 1.525 (2) |
O1—H1X | 0.830 (18) | C8—C9 | 1.539 (2) |
O2—C7 | 1.438 (3) | C8—H8 | 0.9800 |
O2—H2X | 0.835 (16) | C9—C11 | 1.536 (3) |
O3—C15 | 1.418 (3) | C9—C10 | 1.558 (2) |
O3—H3X | 0.844 (17) | C9—H9 | 0.9800 |
O4—C17 | 1.212 (3) | C10—C19 | 1.546 (3) |
O5—H5X | 0.852 (18) | C11—C12 | 1.533 (3) |
O5—H5Y | 0.841 (18) | C11—H11A | 0.9700 |
O6—H6X | 0.84 (2) | C11—H11B | 0.9700 |
O6—H6Y | 0.799 (19) | C12—C13 | 1.518 (3) |
C1—C2 | 1.526 (3) | C12—H12A | 0.9700 |
C1—C10 | 1.544 (3) | C12—H12B | 0.9700 |
C1—H1A | 0.9700 | C13—C17 | 1.518 (3) |
C1—H1B | 0.9700 | C13—C14 | 1.541 (3) |
C2—C3 | 1.505 (3) | C13—C18 | 1.547 (3) |
C2—H2A | 0.9700 | C14—C15 | 1.531 (3) |
C2—H2B | 0.9700 | C14—H14 | 0.9800 |
C3—C4 | 1.509 (3) | C15—C16 | 1.536 (3) |
C3—H3 | 0.9800 | C15—H15 | 0.9800 |
C4—C5 | 1.517 (3) | C16—C17 | 1.503 (3) |
C4—H4A | 0.9700 | C16—H16A | 0.9700 |
C4—H4B | 0.9700 | C16—H16B | 0.9700 |
C5—C6 | 1.324 (3) | C18—H18A | 0.9599 |
C5—C10 | 1.521 (3) | C18—H18B | 0.9599 |
C6—C7 | 1.491 (2) | C18—H18C | 0.9599 |
C6—H6 | 0.9300 | C19—H19A | 0.9599 |
C7—C8 | 1.536 (3) | C19—H19B | 0.9599 |
C7—H7 | 0.9800 | C19—H19C | 0.9599 |
C3—O1—H1X | 110 (2) | C1—C10—C19 | 109.70 (18) |
C7—O2—H2X | 102 (2) | C5—C10—C9 | 108.76 (15) |
C15—O3—H3X | 111 (2) | C1—C10—C9 | 108.25 (15) |
H5X—O5—H5Y | 100 (3) | C19—C10—C9 | 112.24 (16) |
H6X—O6—H6Y | 108 (5) | C12—C11—C9 | 113.61 (17) |
C2—C1—C10 | 114.86 (16) | C12—C11—H11A | 108.8 |
C2—C1—H1A | 108.6 | C9—C11—H11A | 108.8 |
C10—C1—H1A | 108.6 | C12—C11—H11B | 108.8 |
C2—C1—H1B | 108.6 | C9—C11—H11B | 108.8 |
C10—C1—H1B | 108.6 | H11A—C11—H11B | 107.7 |
H1A—C1—H1B | 107.5 | C13—C12—C11 | 110.04 (17) |
C3—C2—C1 | 108.85 (16) | C13—C12—H12A | 109.7 |
C3—C2—H2A | 109.9 | C11—C12—H12A | 109.7 |
C1—C2—H2A | 109.9 | C13—C12—H12B | 109.7 |
C3—C2—H2B | 109.9 | C11—C12—H12B | 109.7 |
C1—C2—H2B | 109.9 | H12A—C12—H12B | 108.2 |
H2A—C2—H2B | 108.3 | C12—C13—C17 | 116.87 (18) |
O1—C3—C2 | 109.45 (16) | C12—C13—C14 | 108.75 (16) |
O1—C3—C4 | 111.19 (16) | C17—C13—C14 | 99.50 (17) |
C2—C3—C4 | 109.54 (17) | C12—C13—C18 | 111.8 (2) |
O1—C3—H3 | 108.9 | C17—C13—C18 | 105.57 (19) |
C2—C3—H3 | 108.9 | C14—C13—C18 | 113.90 (19) |
C4—C3—H3 | 108.9 | C8—C14—C15 | 121.00 (16) |
C3—C4—C5 | 111.50 (15) | C8—C14—C13 | 114.19 (16) |
C3—C4—H4A | 109.3 | C15—C14—C13 | 104.31 (15) |
C5—C4—H4A | 109.3 | C8—C14—H14 | 105.3 |
C3—C4—H4B | 109.3 | C15—C14—H14 | 105.3 |
C5—C4—H4B | 109.3 | C13—C14—H14 | 105.3 |
H4A—C4—H4B | 108.0 | O3—C15—C14 | 109.50 (17) |
C6—C5—C4 | 120.17 (17) | O3—C15—C16 | 112.7 (2) |
C6—C5—C10 | 123.01 (17) | C14—C15—C16 | 102.98 (17) |
C4—C5—C10 | 116.82 (16) | O3—C15—H15 | 110.5 |
C5—C6—C7 | 125.63 (18) | C14—C15—H15 | 110.5 |
C5—C6—H6 | 117.2 | C16—C15—H15 | 110.5 |
C7—C6—H6 | 117.2 | C17—C16—C15 | 106.06 (17) |
O2—C7—C6 | 105.89 (17) | C17—C16—H16A | 110.5 |
O2—C7—C8 | 112.73 (15) | C15—C16—H16A | 110.5 |
C6—C7—C8 | 112.84 (16) | C17—C16—H16B | 110.5 |
O2—C7—H7 | 108.4 | C15—C16—H16B | 110.5 |
C6—C7—H7 | 108.4 | H16A—C16—H16B | 108.7 |
C8—C7—H7 | 108.4 | O4—C17—C16 | 124.8 (2) |
C14—C8—C7 | 111.32 (15) | O4—C17—C13 | 126.6 (2) |
C14—C8—C9 | 109.55 (14) | C16—C17—C13 | 108.55 (17) |
C7—C8—C9 | 109.88 (14) | C13—C18—H18A | 109.5 |
C14—C8—H8 | 108.7 | C13—C18—H18B | 109.5 |
C7—C8—H8 | 108.7 | H18A—C18—H18B | 109.5 |
C9—C8—H8 | 108.7 | C13—C18—H18C | 109.5 |
C11—C9—C8 | 113.58 (15) | H18A—C18—H18C | 109.5 |
C11—C9—C10 | 112.49 (15) | H18B—C18—H18C | 109.5 |
C8—C9—C10 | 111.77 (14) | C10—C19—H19A | 109.5 |
C11—C9—H9 | 106.1 | C10—C19—H19B | 109.5 |
C8—C9—H9 | 106.1 | H19A—C19—H19B | 109.5 |
C10—C9—H9 | 106.1 | C10—C19—H19C | 109.5 |
C5—C10—C1 | 109.81 (15) | H19A—C19—H19C | 109.5 |
C5—C10—C19 | 108.07 (17) | H19B—C19—H19C | 109.5 |
C10—C1—C2—C3 | −57.6 (3) | C11—C9—C10—C19 | −59.7 (2) |
C1—C2—C3—O1 | −175.65 (17) | C8—C9—C10—C19 | 69.4 (2) |
C1—C2—C3—C4 | 62.2 (2) | C8—C9—C11—C12 | 49.8 (3) |
O1—C3—C4—C5 | −179.56 (18) | C10—C9—C11—C12 | 178.05 (18) |
C2—C3—C4—C5 | −58.5 (2) | C9—C11—C12—C13 | −54.7 (3) |
C3—C4—C5—C6 | −130.8 (2) | C11—C12—C13—C17 | 169.47 (19) |
C3—C4—C5—C10 | 49.5 (3) | C11—C12—C13—C14 | 57.9 (2) |
C4—C5—C6—C7 | 179.9 (2) | C11—C12—C13—C18 | −68.7 (2) |
C10—C5—C6—C7 | −0.3 (3) | C7—C8—C14—C15 | −58.5 (2) |
C5—C6—C7—O2 | −113.7 (2) | C9—C8—C14—C15 | 179.81 (17) |
C5—C6—C7—C8 | 10.1 (3) | C7—C8—C14—C13 | 175.67 (16) |
O2—C7—C8—C14 | −40.9 (2) | C9—C8—C14—C13 | 53.9 (2) |
C6—C7—C8—C14 | −160.83 (17) | C12—C13—C14—C8 | −60.2 (2) |
O2—C7—C8—C9 | 80.62 (19) | C17—C13—C14—C8 | 177.07 (16) |
C6—C7—C8—C9 | −39.3 (2) | C18—C13—C14—C8 | 65.2 (2) |
C14—C8—C9—C11 | −47.6 (2) | C12—C13—C14—C15 | 165.60 (17) |
C7—C8—C9—C11 | −170.19 (16) | C17—C13—C14—C15 | 42.9 (2) |
C14—C8—C9—C10 | −176.18 (15) | C18—C13—C14—C15 | −69.0 (2) |
C7—C8—C9—C10 | 61.2 (2) | C8—C14—C15—O3 | 72.0 (2) |
C6—C5—C10—C1 | 138.4 (2) | C13—C14—C15—O3 | −157.68 (18) |
C4—C5—C10—C1 | −41.8 (2) | C8—C14—C15—C16 | −167.8 (2) |
C6—C5—C10—C19 | −101.9 (2) | C13—C14—C15—C16 | −37.5 (2) |
C4—C5—C10—C19 | 77.8 (2) | O3—C15—C16—C17 | 134.6 (2) |
C6—C5—C10—C9 | 20.2 (3) | C14—C15—C16—C17 | 16.7 (3) |
C4—C5—C10—C9 | −160.08 (17) | C15—C16—C17—O4 | −167.5 (2) |
C2—C1—C10—C5 | 46.0 (2) | C15—C16—C17—C13 | 10.4 (3) |
C2—C1—C10—C19 | −72.6 (2) | C12—C13—C17—O4 | 28.5 (3) |
C2—C1—C10—C9 | 164.65 (18) | C14—C13—C17—O4 | 145.3 (2) |
C11—C9—C10—C5 | −179.26 (16) | C18—C13—C17—O4 | −96.5 (3) |
C8—C9—C10—C5 | −50.1 (2) | C12—C13—C17—C16 | −149.3 (2) |
C11—C9—C10—C1 | 61.5 (2) | C14—C13—C17—C16 | −32.6 (2) |
C8—C9—C10—C1 | −169.36 (16) | C18—C13—C17—C16 | 85.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1X···O6 | 0.83 (2) | 1.80 (2) | 2.618 (3) | 170 (3) |
O2—H2X···O3 | 0.84 (2) | 1.98 (2) | 2.755 (2) | 153 (3) |
O3—H3X···O5i | 0.84 (2) | 1.89 (2) | 2.731 (2) | 176 (3) |
O5—H5X···O1ii | 0.85 (2) | 1.95 (2) | 2.778 (2) | 165 (3) |
O5—H5Y···O1iii | 0.84 (2) | 1.87 (2) | 2.702 (2) | 172 (3) |
O6—H6X···O5iv | 0.84 (2) | 1.92 (2) | 2.747 (3) | 168 (5) |
O6—H6Y···O4v | 0.80 (2) | 1.99 (2) | 2.787 (3) | 174 (5) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z+2; (iv) x+3/2, −y+3/2, −z+2; (v) −x+2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C19H28O4·2H2O |
Mr | 356.45 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 6.0653 (8), 12.4906 (16), 25.472 (3) |
V (Å3) | 1929.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.975, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12301, 2539, 2289 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.099, 1.03 |
No. of reflections | 2539 |
No. of parameters | 256 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.21 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1X···O6 | 0.830 (18) | 1.80 (2) | 2.618 (3) | 170 (3) |
O2—H2X···O3 | 0.835 (16) | 1.98 (2) | 2.755 (2) | 153 (3) |
O3—H3X···O5i | 0.844 (17) | 1.889 (18) | 2.731 (2) | 176 (3) |
O5—H5X···O1ii | 0.852 (18) | 1.95 (2) | 2.778 (2) | 165 (3) |
O5—H5Y···O1iii | 0.841 (18) | 1.867 (19) | 2.702 (2) | 172 (3) |
O6—H6X···O5iv | 0.84 (2) | 1.92 (2) | 2.747 (3) | 168 (5) |
O6—H6Y···O4v | 0.799 (19) | 1.99 (2) | 2.787 (3) | 174 (5) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z+2; (iv) x+3/2, −y+3/2, −z+2; (v) −x+2, y+1/2, −z+3/2. |
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Drospirenone is a new contraceptive drug with the special antimineralocorticoid and antiandrogenic properties (Muhn et al., 1995). The title compound, (I), as a key starting material for the synthesis of drospirenone, was obtained by biotransformation with Colletotrichum lini from dehydroepiandrosterone (DHEA) (Romano et al., 2006). We report here the crystal structure of (I).
In (I) (Fig. 1), ring A assumes a slightly twisty chair conformation and ring C takes a regular chair conformation. In ring B, atoms C8 and C9 deviate at 0.242 and -0.503 Å from the mean plane C5—C7/C10, respectively, thus ring B takes a half-chair conformation. Ring D has a somewhat twisty envelope conformation: atoms C13, C15, C16 and C17 are nearly coplanar and atom C14 deviates from their mean plane at 0.625 Å.
In the crystal (Fig. 2), the crystalline water molecules involved in the formation of hydrogen bonding. The intermolecular and intramolecular O—H···O hydrogen bonding are found in the crystal lattice (Table 1).