organic compounds
21-(3-Carboxypropanoyl)-11β,17-dihydroxypregn-4-ene-3,20-dione monohydrate
aSchool of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China, and bBeijing Institute of Pharmacology and Toxicology, Beijing 100850, People's Republic of China
*Correspondence e-mail: xiaojunhai@139.com
In the title compound, C25H34O8·H2O, the two crylohexane rings adopt chair conformations. In the crystal, the organic molecule and the water molecule are linked by O—H⋯O hydrogen bonds, generating a three-dimensional network.
Related literature
For background to glucocorticoids, see: Schäcke et al. (2002). For the synthesis, see: Fang et al. (2007).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S160053681001648X/hb5414sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001648X/hb5414Isup2.hkl
To a solution of hydrocortisone (5.43 g, 15 mmol) in pyridine (75 ml), succinic anhydride (3 g, 30 mmol) was added dropwise with stirring at room temperature. The mixture was refluxed for 8 hrs. After pouring the solution to ice water (100 ml) and adjusting pH to 5.0-5.5 with 5% HCl (aq), the resulting white solid was obtained and then collected by filtration, washed with water and dried (Fang et al., 2007). Colourless prisms of (I) were recrystalized from ethanol by the slow evaporation of the solvent at room temperature after several days, presumably the water of crystallisation was absorbed from the atmosphere.
Anomalous dispersion was negliglble and Friedel pairs were merged before
H atoms of water molecule were located in a difference Fourier map and then refined in riding mode with Uiso(H)=1.5Ueq(O).All the other H atoms were placed in idealized locations as riding atoms, with Uiso(H) = 1.2Ueq(C) for methylene, Uiso(H) = 1.5Ueq(C) for methyl groups and Uiso(H) = 1.5Ueq(O) for hydroxyl groups.Glucocorticoids (GCs) process varied biological properties such as anti-inflammatory, immunosuppressive and countershock activities (Schäcke et al., 2002). In view of these importances and to determine the
a crystallographic study of the title compound has been carried out.The molecular structure is shown in Fig. 1. All the bond lengths and angles are within normal ranges. The molecule contains three six-membered rings (A ring atoms C1-C5/C18; B ring atoms C5-C8/C17/C18; C ring atoms C8/C9/C13/C15-C17) and a five-member ring (D ring atoms C9-C13). Ring B and C adopt chair conformations.
In the
the molecules are linked via intermolecular O2—H2···O8, O7—H7···O1 interactions. The molecules and water are additionally linked by strong O3—H3A···O9, O9—H2W···O2, O9—H1W···O1 actions (Fig. 2).For background to glucocorticoids, see: Schäcke et al. (2002). For the synthesis, see: Fang et al. (2007).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. Crystal structure of (I) with displacement ellipsoids shown at the 50% probability level. |
C25H34O8·H2O | F(000) = 1032 |
Mr = 480.54 | Dx = 1.322 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 17248 reflections |
a = 7.2672 (15) Å | θ = 3.1–27.5° |
b = 16.606 (3) Å | µ = 0.10 mm−1 |
c = 20.009 (4) Å | T = 293 K |
V = 2414.7 (8) Å3 | Prism, colourless |
Z = 4 | 0.16 × 0.14 × 0.13 mm |
Rigaku R-AXIS RAPID IP diffractometer | 2562 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.051 |
Graphite monochromator | θmax = 26.5°, θmin = 3.1° |
oscillation scans | h = −8→9 |
21231 measured reflections | k = −20→20 |
2848 independent reflections | l = −25→25 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.063P)2 + 0.2837P] where P = (Fo2 + 2Fc2)/3 |
2848 reflections | (Δ/σ)max < 0.001 |
309 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C25H34O8·H2O | V = 2414.7 (8) Å3 |
Mr = 480.54 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.2672 (15) Å | µ = 0.10 mm−1 |
b = 16.606 (3) Å | T = 293 K |
c = 20.009 (4) Å | 0.16 × 0.14 × 0.13 mm |
Rigaku R-AXIS RAPID IP diffractometer | 2562 reflections with I > 2σ(I) |
21231 measured reflections | Rint = 0.051 |
2848 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.16 e Å−3 |
2848 reflections | Δρmin = −0.17 e Å−3 |
309 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | −0.0416 (3) | 0.95164 (11) | 1.23851 (7) | 0.0557 (5) | |
O2 | −0.0242 (3) | 1.00698 (11) | 0.89550 (9) | 0.0653 (6) | |
H2 | −0.1156 | 1.0337 | 0.9049 | 0.098* | |
O3 | 0.0626 (3) | 0.71841 (10) | 0.80452 (8) | 0.0564 (5) | |
H3A | 0.0723 | 0.6798 | 0.7792 | 0.085* | |
O4 | 0.2230 (3) | 0.83520 (14) | 0.67050 (8) | 0.0713 (6) | |
O5 | −0.1210 (3) | 0.82035 (12) | 0.62841 (8) | 0.0603 (5) | |
O6 | 0.0212 (3) | 0.72295 (11) | 0.57042 (8) | 0.0611 (5) | |
O7 | 0.0666 (3) | 0.85527 (12) | 0.34091 (8) | 0.0658 (6) | |
H7 | 0.0474 | 0.8889 | 0.3117 | 0.099* | |
O8 | −0.1085 (3) | 0.93713 (12) | 0.40118 (10) | 0.0690 (6) | |
O9 | 0.0883 (3) | 0.57919 (13) | 0.73352 (10) | 0.0763 (6) | |
H2W | 0.0463 | 0.5672 | 0.6951 | 0.114* | |
H1W | 0.2019 | 0.5690 | 0.7392 | 0.114* | |
C1 | −0.1098 (3) | 0.96647 (15) | 1.06144 (10) | 0.0436 (5) | |
H1A | −0.1831 | 0.9991 | 1.0313 | 0.052* | |
H1B | −0.1630 | 0.9129 | 1.0624 | 0.052* | |
C2 | −0.1196 (4) | 1.00276 (15) | 1.13148 (11) | 0.0520 (6) | |
H2B | −0.0803 | 1.0585 | 1.1299 | 0.062* | |
H2C | −0.2459 | 1.0015 | 1.1472 | 0.062* | |
C3 | −0.0006 (4) | 0.95744 (14) | 1.17876 (10) | 0.0444 (5) | |
C4 | 0.1676 (4) | 0.92345 (15) | 1.15279 (11) | 0.0448 (5) | |
H4A | 0.2477 | 0.8984 | 1.1825 | 0.054* | |
C5 | 0.2140 (3) | 0.92622 (13) | 1.08788 (10) | 0.0374 (5) | |
C6 | 0.4020 (3) | 0.90065 (16) | 1.06572 (11) | 0.0477 (6) | |
H6A | 0.4626 | 0.8727 | 1.1022 | 0.057* | |
H6B | 0.4742 | 0.9481 | 1.0552 | 0.057* | |
C7 | 0.3970 (3) | 0.84573 (15) | 1.00483 (10) | 0.0458 (5) | |
H7A | 0.3440 | 0.7943 | 1.0174 | 0.055* | |
H7B | 0.5217 | 0.8361 | 0.9895 | 0.055* | |
C8 | 0.2841 (3) | 0.88213 (12) | 0.94764 (10) | 0.0339 (4) | |
H8A | 0.3439 | 0.9315 | 0.9320 | 0.041* | |
C9 | 0.2692 (3) | 0.82262 (13) | 0.88998 (10) | 0.0369 (4) | |
H9A | 0.2057 | 0.7750 | 0.9074 | 0.044* | |
C10 | 0.4473 (4) | 0.79267 (17) | 0.85697 (12) | 0.0535 (6) | |
H10A | 0.5027 | 0.7497 | 0.8829 | 0.064* | |
H10B | 0.5355 | 0.8361 | 0.8522 | 0.064* | |
C11 | 0.3832 (4) | 0.76156 (16) | 0.78761 (12) | 0.0549 (7) | |
H11A | 0.4528 | 0.7874 | 0.7522 | 0.066* | |
H11B | 0.4011 | 0.7038 | 0.7844 | 0.066* | |
C12 | 0.1772 (3) | 0.78255 (13) | 0.78154 (10) | 0.0418 (5) | |
C13 | 0.1533 (3) | 0.85407 (12) | 0.83136 (9) | 0.0356 (5) | |
C14 | 0.2382 (4) | 0.93041 (13) | 0.80015 (11) | 0.0478 (6) | |
H14A | 0.2240 | 0.9748 | 0.8304 | 0.072* | |
H14B | 0.1768 | 0.9424 | 0.7589 | 0.072* | |
H14C | 0.3666 | 0.9215 | 0.7917 | 0.072* | |
C15 | −0.0418 (3) | 0.86831 (17) | 0.85699 (10) | 0.0447 (5) | |
H15A | −0.0955 | 0.8170 | 0.8694 | 0.054* | |
H15B | −0.1155 | 0.8907 | 0.8211 | 0.054* | |
C16 | −0.0500 (3) | 0.92549 (15) | 0.91754 (11) | 0.0445 (5) | |
H16A | −0.1738 | 0.9216 | 0.9367 | 0.053* | |
C17 | 0.0888 (3) | 0.90217 (12) | 0.97298 (9) | 0.0327 (4) | |
H17A | 0.0421 | 0.8512 | 0.9908 | 0.039* | |
C18 | 0.0874 (3) | 0.96102 (12) | 1.03428 (9) | 0.0343 (4) | |
C19 | 0.1631 (4) | 1.04641 (13) | 1.01880 (11) | 0.0494 (6) | |
H19A | 0.1587 | 1.0787 | 1.0586 | 0.074* | |
H19B | 0.0893 | 1.0710 | 0.9846 | 0.074* | |
H19C | 0.2881 | 1.0423 | 1.0036 | 0.074* | |
C20 | 0.1216 (4) | 0.80295 (14) | 0.70948 (10) | 0.0484 (6) | |
C21 | −0.0732 (4) | 0.78122 (19) | 0.68959 (11) | 0.0589 (7) | |
H21A | −0.0833 | 0.7233 | 0.6841 | 0.071* | |
H21B | −0.1578 | 0.7976 | 0.7245 | 0.071* | |
C22 | −0.0565 (3) | 0.78637 (15) | 0.57212 (11) | 0.0449 (5) | |
C23 | −0.1019 (4) | 0.83901 (14) | 0.51351 (10) | 0.0453 (5) | |
H23A | −0.0684 | 0.8941 | 0.5241 | 0.054* | |
H23B | −0.2337 | 0.8375 | 0.5060 | 0.054* | |
C24 | −0.0045 (4) | 0.81402 (14) | 0.45007 (11) | 0.0491 (6) | |
H24A | 0.1253 | 0.8064 | 0.4595 | 0.059* | |
H24B | −0.0540 | 0.7629 | 0.4349 | 0.059* | |
C25 | −0.0252 (4) | 0.87517 (15) | 0.39558 (11) | 0.0466 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0697 (12) | 0.0668 (11) | 0.0306 (8) | −0.0100 (10) | 0.0046 (8) | 0.0002 (7) |
O2 | 0.0894 (15) | 0.0594 (11) | 0.0469 (10) | 0.0358 (11) | −0.0174 (10) | 0.0003 (8) |
O3 | 0.0850 (14) | 0.0468 (9) | 0.0373 (8) | −0.0218 (9) | 0.0110 (9) | −0.0018 (7) |
O4 | 0.0798 (14) | 0.0982 (15) | 0.0358 (9) | −0.0302 (13) | 0.0077 (9) | 0.0125 (9) |
O5 | 0.0673 (12) | 0.0787 (12) | 0.0349 (8) | 0.0154 (11) | 0.0019 (8) | −0.0053 (8) |
O6 | 0.0848 (14) | 0.0542 (10) | 0.0443 (9) | 0.0136 (10) | 0.0007 (9) | −0.0003 (8) |
O7 | 0.0914 (15) | 0.0696 (12) | 0.0363 (8) | 0.0176 (12) | 0.0047 (10) | 0.0010 (8) |
O8 | 0.0811 (14) | 0.0663 (12) | 0.0597 (11) | 0.0290 (12) | 0.0072 (11) | 0.0108 (9) |
O9 | 0.0737 (14) | 0.0851 (14) | 0.0703 (12) | −0.0039 (13) | −0.0130 (12) | −0.0341 (11) |
C1 | 0.0407 (12) | 0.0587 (13) | 0.0314 (10) | 0.0081 (11) | 0.0005 (9) | −0.0009 (9) |
C2 | 0.0586 (15) | 0.0618 (14) | 0.0357 (11) | 0.0119 (13) | 0.0065 (11) | −0.0032 (10) |
C3 | 0.0564 (14) | 0.0447 (11) | 0.0321 (10) | −0.0107 (11) | 0.0000 (10) | −0.0025 (9) |
C4 | 0.0513 (14) | 0.0504 (12) | 0.0328 (10) | −0.0016 (11) | −0.0084 (10) | 0.0051 (9) |
C5 | 0.0381 (11) | 0.0396 (10) | 0.0345 (10) | −0.0028 (9) | −0.0082 (9) | 0.0011 (8) |
C6 | 0.0396 (12) | 0.0659 (14) | 0.0378 (11) | 0.0060 (11) | −0.0101 (10) | 0.0008 (10) |
C7 | 0.0392 (12) | 0.0571 (13) | 0.0411 (11) | 0.0125 (11) | −0.0062 (10) | 0.0020 (10) |
C8 | 0.0311 (10) | 0.0388 (10) | 0.0319 (9) | 0.0013 (9) | −0.0021 (8) | 0.0020 (8) |
C9 | 0.0383 (11) | 0.0375 (10) | 0.0349 (10) | 0.0039 (9) | 0.0009 (9) | 0.0019 (8) |
C10 | 0.0490 (14) | 0.0601 (14) | 0.0516 (13) | 0.0175 (12) | 0.0045 (11) | −0.0039 (11) |
C11 | 0.0634 (17) | 0.0563 (14) | 0.0450 (13) | 0.0122 (13) | 0.0094 (13) | −0.0054 (11) |
C12 | 0.0536 (14) | 0.0412 (11) | 0.0307 (10) | −0.0060 (10) | 0.0060 (9) | 0.0007 (9) |
C13 | 0.0394 (11) | 0.0387 (10) | 0.0287 (9) | −0.0012 (9) | 0.0012 (8) | 0.0017 (8) |
C14 | 0.0596 (15) | 0.0401 (11) | 0.0436 (12) | −0.0036 (12) | −0.0009 (11) | 0.0081 (9) |
C15 | 0.0370 (12) | 0.0667 (14) | 0.0303 (9) | 0.0017 (11) | −0.0048 (9) | −0.0044 (10) |
C16 | 0.0349 (11) | 0.0643 (14) | 0.0343 (10) | 0.0118 (11) | −0.0054 (9) | −0.0039 (10) |
C17 | 0.0320 (10) | 0.0371 (10) | 0.0289 (9) | −0.0002 (8) | −0.0023 (8) | 0.0022 (7) |
C18 | 0.0379 (11) | 0.0362 (10) | 0.0286 (9) | 0.0023 (9) | −0.0016 (8) | 0.0038 (8) |
C19 | 0.0647 (16) | 0.0405 (11) | 0.0431 (12) | −0.0053 (12) | −0.0013 (11) | 0.0029 (9) |
C20 | 0.0634 (16) | 0.0528 (13) | 0.0290 (10) | −0.0045 (12) | 0.0071 (11) | −0.0016 (9) |
C21 | 0.0637 (17) | 0.0807 (18) | 0.0322 (11) | −0.0067 (15) | 0.0042 (11) | −0.0002 (12) |
C22 | 0.0436 (12) | 0.0530 (13) | 0.0380 (11) | −0.0041 (11) | −0.0010 (10) | −0.0058 (10) |
C23 | 0.0470 (13) | 0.0496 (12) | 0.0394 (11) | 0.0029 (11) | −0.0034 (10) | −0.0015 (9) |
C24 | 0.0617 (15) | 0.0470 (12) | 0.0387 (11) | 0.0075 (12) | −0.0039 (11) | −0.0013 (10) |
C25 | 0.0501 (14) | 0.0531 (13) | 0.0366 (11) | 0.0027 (12) | −0.0061 (10) | −0.0042 (10) |
O1—C3 | 1.236 (3) | C9—C10 | 1.536 (3) |
O2—C16 | 1.436 (3) | C9—H9A | 0.9800 |
O2—H2 | 0.8200 | C10—C11 | 1.552 (4) |
O3—C12 | 1.428 (3) | C10—H10A | 0.9700 |
O3—H3A | 0.8200 | C10—H10B | 0.9700 |
O4—C20 | 1.199 (3) | C11—C12 | 1.542 (4) |
O5—C22 | 1.344 (3) | C11—H11A | 0.9700 |
O5—C21 | 1.429 (3) | C11—H11B | 0.9700 |
O6—C22 | 1.195 (3) | C12—C20 | 1.535 (3) |
O7—C25 | 1.323 (3) | C12—C13 | 1.560 (3) |
O7—H7 | 0.8200 | C13—C15 | 1.526 (3) |
O8—C25 | 1.199 (3) | C13—C14 | 1.542 (3) |
O9—H2W | 0.8502 | C14—H14A | 0.9600 |
O9—H1W | 0.8500 | C14—H14B | 0.9600 |
C1—C2 | 1.527 (3) | C14—H14C | 0.9600 |
C1—C18 | 1.536 (3) | C15—C16 | 1.540 (3) |
C1—H1A | 0.9700 | C15—H15A | 0.9700 |
C1—H1B | 0.9700 | C15—H15B | 0.9700 |
C2—C3 | 1.486 (4) | C16—C17 | 1.548 (3) |
C2—H2B | 0.9700 | C16—H16A | 0.9800 |
C2—H2C | 0.9700 | C17—C18 | 1.568 (3) |
C3—C4 | 1.443 (4) | C17—H17A | 0.9800 |
C4—C5 | 1.343 (3) | C18—C19 | 1.552 (3) |
C4—H4A | 0.9300 | C19—H19A | 0.9600 |
C5—C6 | 1.498 (3) | C19—H19B | 0.9600 |
C5—C18 | 1.526 (3) | C19—H19C | 0.9600 |
C6—C7 | 1.522 (3) | C20—C21 | 1.514 (4) |
C6—H6A | 0.9700 | C21—H21A | 0.9700 |
C6—H6B | 0.9700 | C21—H21B | 0.9700 |
C7—C8 | 1.532 (3) | C22—C23 | 1.499 (3) |
C7—H7A | 0.9700 | C23—C24 | 1.511 (3) |
C7—H7B | 0.9700 | C23—H23A | 0.9700 |
C8—C9 | 1.523 (3) | C23—H23B | 0.9700 |
C8—C17 | 1.543 (3) | C24—C25 | 1.498 (3) |
C8—H8A | 0.9800 | C24—H24A | 0.9700 |
C9—C13 | 1.536 (3) | C24—H24B | 0.9700 |
C16—O2—H2 | 109.5 | C15—C13—C14 | 112.4 (2) |
C12—O3—H3A | 109.5 | C9—C13—C14 | 111.68 (19) |
C22—O5—C21 | 116.3 (2) | C15—C13—C12 | 115.87 (19) |
C25—O7—H7 | 109.5 | C9—C13—C12 | 99.67 (16) |
H2W—O9—H1W | 115.0 | C14—C13—C12 | 108.81 (16) |
C2—C1—C18 | 113.05 (19) | C13—C14—H14A | 109.5 |
C2—C1—H1A | 109.0 | C13—C14—H14B | 109.5 |
C18—C1—H1A | 109.0 | H14A—C14—H14B | 109.5 |
C2—C1—H1B | 109.0 | C13—C14—H14C | 109.5 |
C18—C1—H1B | 109.0 | H14A—C14—H14C | 109.5 |
H1A—C1—H1B | 107.8 | H14B—C14—H14C | 109.5 |
C3—C2—C1 | 110.9 (2) | C13—C15—C16 | 113.31 (18) |
C3—C2—H2B | 109.5 | C13—C15—H15A | 108.9 |
C1—C2—H2B | 109.5 | C16—C15—H15A | 108.9 |
C3—C2—H2C | 109.5 | C13—C15—H15B | 108.9 |
C1—C2—H2C | 109.5 | C16—C15—H15B | 108.9 |
H2B—C2—H2C | 108.0 | H15A—C15—H15B | 107.7 |
O1—C3—C4 | 121.4 (2) | O2—C16—C15 | 109.54 (19) |
O1—C3—C2 | 121.0 (2) | O2—C16—C17 | 111.77 (19) |
C4—C3—C2 | 117.49 (19) | C15—C16—C17 | 112.59 (18) |
C5—C4—C3 | 123.2 (2) | O2—C16—H16A | 107.6 |
C5—C4—H4A | 118.4 | C15—C16—H16A | 107.6 |
C3—C4—H4A | 118.4 | C17—C16—H16A | 107.6 |
C4—C5—C6 | 120.4 (2) | C8—C17—C16 | 114.68 (16) |
C4—C5—C18 | 122.8 (2) | C8—C17—C18 | 113.40 (17) |
C6—C5—C18 | 116.67 (18) | C16—C17—C18 | 113.60 (17) |
C5—C6—C7 | 112.63 (19) | C8—C17—H17A | 104.6 |
C5—C6—H6A | 109.1 | C16—C17—H17A | 104.6 |
C7—C6—H6A | 109.1 | C18—C17—H17A | 104.6 |
C5—C6—H6B | 109.1 | C5—C18—C1 | 109.64 (16) |
C7—C6—H6B | 109.1 | C5—C18—C19 | 105.83 (18) |
H6A—C6—H6B | 107.8 | C1—C18—C19 | 110.34 (19) |
C6—C7—C8 | 111.99 (18) | C5—C18—C17 | 108.04 (16) |
C6—C7—H7A | 109.2 | C1—C18—C17 | 108.62 (17) |
C8—C7—H7A | 109.2 | C19—C18—C17 | 114.26 (16) |
C6—C7—H7B | 109.2 | C18—C19—H19A | 109.5 |
C8—C7—H7B | 109.2 | C18—C19—H19B | 109.5 |
H7A—C7—H7B | 107.9 | H19A—C19—H19B | 109.5 |
C9—C8—C7 | 110.37 (17) | C18—C19—H19C | 109.5 |
C9—C8—C17 | 108.86 (17) | H19A—C19—H19C | 109.5 |
C7—C8—C17 | 109.39 (16) | H19B—C19—H19C | 109.5 |
C9—C8—H8A | 109.4 | O4—C20—C21 | 120.7 (2) |
C7—C8—H8A | 109.4 | O4—C20—C12 | 123.2 (3) |
C17—C8—H8A | 109.4 | C21—C20—C12 | 116.1 (2) |
C8—C9—C13 | 113.40 (17) | O5—C21—C20 | 110.1 (2) |
C8—C9—C10 | 118.41 (19) | O5—C21—H21A | 109.6 |
C13—C9—C10 | 104.11 (17) | C20—C21—H21A | 109.6 |
C8—C9—H9A | 106.7 | O5—C21—H21B | 109.6 |
C13—C9—H9A | 106.7 | C20—C21—H21B | 109.6 |
C10—C9—H9A | 106.7 | H21A—C21—H21B | 108.2 |
C9—C10—C11 | 103.9 (2) | O6—C22—O5 | 123.9 (2) |
C9—C10—H10A | 111.0 | O6—C22—C23 | 126.5 (2) |
C11—C10—H10A | 111.0 | O5—C22—C23 | 109.5 (2) |
C9—C10—H10B | 111.0 | C22—C23—C24 | 113.2 (2) |
C11—C10—H10B | 111.0 | C22—C23—H23A | 108.9 |
H10A—C10—H10B | 109.0 | C24—C23—H23A | 108.9 |
C12—C11—C10 | 106.6 (2) | C22—C23—H23B | 108.9 |
C12—C11—H11A | 110.4 | C24—C23—H23B | 108.9 |
C10—C11—H11A | 110.4 | H23A—C23—H23B | 107.8 |
C12—C11—H11B | 110.4 | C25—C24—C23 | 112.2 (2) |
C10—C11—H11B | 110.4 | C25—C24—H24A | 109.2 |
H11A—C11—H11B | 108.6 | C23—C24—H24A | 109.2 |
O3—C12—C20 | 108.3 (2) | C25—C24—H24B | 109.2 |
O3—C12—C11 | 111.9 (2) | C23—C24—H24B | 109.2 |
C20—C12—C11 | 112.3 (2) | H24A—C24—H24B | 107.9 |
O3—C12—C13 | 107.28 (17) | O8—C25—O7 | 123.1 (2) |
C20—C12—C13 | 113.75 (18) | O8—C25—C24 | 124.4 (2) |
C11—C12—C13 | 103.30 (19) | O7—C25—C24 | 112.4 (2) |
C15—C13—C9 | 107.79 (16) | ||
C18—C1—C2—C3 | −55.5 (3) | C13—C15—C16—C17 | −49.1 (3) |
C1—C2—C3—O1 | −148.7 (2) | C9—C8—C17—C16 | −49.2 (2) |
C1—C2—C3—C4 | 33.7 (3) | C7—C8—C17—C16 | −169.87 (18) |
O1—C3—C4—C5 | 177.8 (2) | C9—C8—C17—C18 | 178.04 (15) |
C2—C3—C4—C5 | −4.7 (4) | C7—C8—C17—C18 | 57.4 (2) |
C3—C4—C5—C6 | 171.1 (2) | O2—C16—C17—C8 | −78.2 (2) |
C3—C4—C5—C18 | −4.0 (4) | C15—C16—C17—C8 | 45.6 (3) |
C4—C5—C6—C7 | 134.0 (2) | O2—C16—C17—C18 | 54.4 (2) |
C18—C5—C6—C7 | −50.7 (3) | C15—C16—C17—C18 | 178.24 (19) |
C5—C6—C7—C8 | 52.3 (3) | C4—C5—C18—C1 | −17.2 (3) |
C6—C7—C8—C9 | −175.34 (19) | C6—C5—C18—C1 | 167.61 (19) |
C6—C7—C8—C17 | −55.6 (3) | C4—C5—C18—C19 | 101.8 (2) |
C7—C8—C9—C13 | 178.47 (18) | C6—C5—C18—C19 | −73.4 (2) |
C17—C8—C9—C13 | 58.4 (2) | C4—C5—C18—C17 | −135.4 (2) |
C7—C8—C9—C10 | −59.1 (3) | C6—C5—C18—C17 | 49.4 (2) |
C17—C8—C9—C10 | −179.18 (19) | C2—C1—C18—C5 | 46.3 (3) |
C8—C9—C10—C11 | −159.65 (19) | C2—C1—C18—C19 | −69.9 (2) |
C13—C9—C10—C11 | −32.7 (2) | C2—C1—C18—C17 | 164.16 (18) |
C9—C10—C11—C12 | 5.4 (3) | C8—C17—C18—C5 | −52.8 (2) |
C10—C11—C12—O3 | −91.9 (2) | C16—C17—C18—C5 | 173.95 (18) |
C10—C11—C12—C20 | 146.2 (2) | C8—C17—C18—C1 | −171.64 (17) |
C10—C11—C12—C13 | 23.2 (2) | C16—C17—C18—C1 | 55.1 (2) |
C8—C9—C13—C15 | −62.0 (2) | C8—C17—C18—C19 | 64.7 (2) |
C10—C9—C13—C15 | 168.0 (2) | C16—C17—C18—C19 | −68.6 (2) |
C8—C9—C13—C14 | 61.9 (2) | O3—C12—C20—O4 | −156.6 (3) |
C10—C9—C13—C14 | −68.2 (2) | C11—C12—C20—O4 | −32.6 (3) |
C8—C9—C13—C12 | 176.70 (18) | C13—C12—C20—O4 | 84.3 (3) |
C10—C9—C13—C12 | 46.7 (2) | O3—C12—C20—C21 | 24.4 (3) |
O3—C12—C13—C15 | −39.4 (3) | C11—C12—C20—C21 | 148.4 (2) |
C20—C12—C13—C15 | 80.3 (2) | C13—C12—C20—C21 | −94.7 (3) |
C11—C12—C13—C15 | −157.70 (19) | C22—O5—C21—C20 | 79.2 (3) |
O3—C12—C13—C9 | 75.9 (2) | O4—C20—C21—O5 | −13.1 (4) |
C20—C12—C13—C9 | −164.4 (2) | C12—C20—C21—O5 | 165.9 (2) |
C11—C12—C13—C9 | −42.4 (2) | C21—O5—C22—O6 | 7.3 (4) |
O3—C12—C13—C14 | −167.12 (19) | C21—O5—C22—C23 | −174.2 (2) |
C20—C12—C13—C14 | −47.4 (3) | O6—C22—C23—C24 | −12.4 (4) |
C11—C12—C13—C14 | 74.6 (2) | O5—C22—C23—C24 | 169.1 (2) |
C9—C13—C15—C16 | 55.8 (3) | C22—C23—C24—C25 | −170.0 (2) |
C14—C13—C15—C16 | −67.6 (2) | C23—C24—C25—O8 | 0.3 (4) |
C12—C13—C15—C16 | 166.44 (18) | C23—C24—C25—O7 | 177.2 (2) |
C13—C15—C16—O2 | 75.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O8i | 0.82 | 2.06 | 2.828 (3) | 155 |
O3—H3A···O9 | 0.82 | 1.91 | 2.720 (2) | 170 |
O7—H7···O1ii | 0.82 | 1.91 | 2.716 (2) | 167 |
O9—H2W···O2iii | 0.85 | 2.08 | 2.884 (3) | 158 |
O9—H1W···O1iv | 0.85 | 1.95 | 2.795 (3) | 174 |
Symmetry codes: (i) −x−1/2, −y+2, z+1/2; (ii) x, y, z−1; (iii) −x, y−1/2, −z+3/2; (iv) x+1/2, −y+3/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C25H34O8·H2O |
Mr | 480.54 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 7.2672 (15), 16.606 (3), 20.009 (4) |
V (Å3) | 2414.7 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.16 × 0.14 × 0.13 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21231, 2848, 2562 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.106, 1.06 |
No. of reflections | 2848 |
No. of parameters | 309 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.17 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O8i | 0.82 | 2.06 | 2.828 (3) | 155 |
O3—H3A···O9 | 0.82 | 1.91 | 2.720 (2) | 170 |
O7—H7···O1ii | 0.82 | 1.91 | 2.716 (2) | 167 |
O9—H2W···O2iii | 0.85 | 2.08 | 2.884 (3) | 158 |
O9—H1W···O1iv | 0.85 | 1.95 | 2.795 (3) | 174 |
Symmetry codes: (i) −x−1/2, −y+2, z+1/2; (ii) x, y, z−1; (iii) −x, y−1/2, −z+3/2; (iv) x+1/2, −y+3/2, −z+2. |
Acknowledgements
The authors thank Dr Yi-Ying Gao (Institute of Process Engineering, Chinese Academy of Science, Beijing) for the structure analysis.
References
Fang, L., Zhang, Y. Y., Lehmann, J., Wang, Y., Ji, H. & Ding, D. Y (2007). Bioorg. Med. Chem. Lett. 17, 1062–1066. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Schäcke, H., Döcke, W. D. & Asadullah, K. (2002). Pharmacol. Ther. 96, 23–43. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Glucocorticoids (GCs) process varied biological properties such as anti-inflammatory, immunosuppressive and countershock activities (Schäcke et al., 2002). In view of these importances and to determine the molecular conformation, a crystallographic study of the title compound has been carried out.
The molecular structure is shown in Fig. 1. All the bond lengths and angles are within normal ranges. The molecule contains three six-membered rings (A ring atoms C1-C5/C18; B ring atoms C5-C8/C17/C18; C ring atoms C8/C9/C13/C15-C17) and a five-member ring (D ring atoms C9-C13). Ring B and C adopt chair conformations.
In the crystal structure, the molecules are linked via intermolecular O2—H2···O8, O7—H7···O1 interactions. The molecules and water are additionally linked by strong O3—H3A···O9, O9—H2W···O2, O9—H1W···O1 actions (Fig. 2).