Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036732/cv2284sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036732/cv2284Isup2.hkl |
CCDC reference: 657887
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.102
- Data-to-parameter ratio = 10.7
checkCIF/PLATON results
No syntax errors found
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 2274 Count of symmetry unique reflns 2289 Completeness (_total/calc) 99.34% 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 C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 5 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 0 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 literature describing similar structures with similar properties to the title compound, see: Nitta et al. (1985); Reisch et al. (1993); Sheng et al. (2007); Xia et al. (2005).
For related literature, see: Patil et al. (2002).
Pregna-1,4,16-triene-3,20-dione was synthesized according to Patil et al. (2002) in a form of a powder. Crystals of (I) suitable for structure analysis were obtained by slow evaporation from a mixture of tetrahydrofuran, acetone and water (4:4:2, v/v).
Due to absence of any significant anomalous scatterers in the molecule, the 1591 Friedel pairs were merged before the final refinement. The absolute configuration was assigned to correspond with that of the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of the title compound. The C-bound H atoms were placed at calculated positions (C—H 0.93–0.98 Å) and constrained to ride on their parent atoms, withUiso(Hmethyl) = 1.5Ueq(Cmethyl) or Uiso(Hnon-methyl) = 1.2Ueq(Cnon-methyl).
The title compound, (I), is used in the synthesis of prednisolone, because the ring A is fully functionalized a 1,4-dien-3-one system (Nitta et al., 1985). We present here its crystal structure, which exhibits the crystal packing close to those observed in 17α-hydroxy-4-pregnen-20-yn-3-one (II) (Reisch et al., 1993) and 17α-hydroxypregna-1,4-diene-3,20-dione (III) (Sheng et al., 2007). In (I) (Fig. 1), all bond lengths and angles agree with those in (II) and (III). The C1═C2, C4═C5, C16═C17, O1—C3 and O2—C18 distances are 1.326 (3) Å, 1.332 (3) Å, 1.332 (3) Å, 1.226 (3) Å and 1.221 (2) Å, respectively.
Ring A and atoms O1 and C6 are almost coplanar with the r.m.s. deviation of 0.061 (1) Å. Rings B and C show normal chair conformations, which are very similar to those reported by Xia et al. (2005). Ring D has an envelope conformation with atom C14 deviating at 0.589 (3) Å from the mean plane C13/C15/C16/C17 [in spite of structures (II) and (III) with the most deviating atom C13].
In the crystal, the weak intermolecular C—H···O hydrogen bonds (Table 1) stabilize the packing (Fig. 2).
For literature describing similar structures with similar properties to the title compound, see: Nitta et al. (1985); Reisch et al. (1993); Sheng et al. (2007); Xia et al. (2005).
For related literature, see: Patil et al. (2002).
Data collection: APEX2 (Bruker, ????); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
Fig. 1. The structure of (I) with 30% probability displacement ellipsoids. | |
Fig. 2. Packing diagram of (I), viewed along the b axis. Hydrogen- bonds are shown as dashed lines. |
C21H26O2 | F(000) = 672 |
Mr = 310.42 | Dx = 1.199 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3759 reflections |
a = 6.3625 (12) Å | θ = 3.2–26.9° |
b = 11.745 (2) Å | µ = 0.08 mm−1 |
c = 23.007 (4) Å | T = 296 K |
V = 1719.2 (5) Å3 | Block, pale yellow |
Z = 4 | 0.25 × 0.20 × 0.15 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 2274 independent reflections |
Radiation source: fine-focus sealed tube | 1871 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→6 |
Tmin = 0.981, Tmax = 0.999 | k = −15→12 |
10912 measured reflections | l = −26→29 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0456P)2 + 0.2215P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.102 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.15 e Å−3 |
2274 reflections | Δρmin = −0.13 e Å−3 |
212 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0073 (16) |
Primary atom site location: structure-invariant direct methods | Absolute structure: see text |
Secondary atom site location: difference Fourier map |
C21H26O2 | V = 1719.2 (5) Å3 |
Mr = 310.42 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.3625 (12) Å | µ = 0.08 mm−1 |
b = 11.745 (2) Å | T = 296 K |
c = 23.007 (4) Å | 0.25 × 0.20 × 0.15 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 2274 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1871 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.999 | Rint = 0.028 |
10912 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.15 e Å−3 |
2274 reflections | Δρmin = −0.13 e Å−3 |
212 parameters | Absolute structure: see text |
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 | 0.9371 (4) | 0.57024 (18) | 0.48495 (8) | 0.1004 (7) | |
O2 | 1.2908 (3) | 0.79394 (18) | 0.91843 (8) | 0.0839 (6) | |
C1 | 1.0192 (4) | 0.7610 (2) | 0.60194 (9) | 0.0619 (6) | |
H1 | 1.1142 | 0.8176 | 0.6123 | 0.074* | |
C2 | 1.0551 (4) | 0.7048 (3) | 0.55291 (10) | 0.0723 (7) | |
H2 | 1.1738 | 0.7224 | 0.5311 | 0.087* | |
C3 | 0.9126 (5) | 0.6160 (2) | 0.53236 (10) | 0.0683 (7) | |
C4 | 0.7407 (4) | 0.5879 (2) | 0.57074 (9) | 0.0625 (6) | |
H4 | 0.6524 | 0.5281 | 0.5603 | 0.075* | |
C5 | 0.7016 (3) | 0.64276 (17) | 0.62024 (9) | 0.0501 (5) | |
C6 | 0.5246 (4) | 0.6074 (2) | 0.65934 (9) | 0.0617 (6) | |
H6A | 0.4533 | 0.5420 | 0.6427 | 0.074* | |
H6B | 0.4237 | 0.6690 | 0.6625 | 0.074* | |
C7 | 0.6068 (4) | 0.57713 (18) | 0.71942 (9) | 0.0551 (6) | |
H7A | 0.6922 | 0.5089 | 0.7168 | 0.066* | |
H7B | 0.4891 | 0.5609 | 0.7449 | 0.066* | |
C8 | 0.7380 (3) | 0.67328 (16) | 0.74551 (8) | 0.0428 (4) | |
H8 | 0.6477 | 0.7398 | 0.7515 | 0.051* | |
C9 | 0.9196 (3) | 0.70629 (16) | 0.70402 (8) | 0.0406 (4) | |
H9 | 1.0036 | 0.6371 | 0.6987 | 0.049* | |
C10 | 0.8374 (3) | 0.74005 (16) | 0.64175 (8) | 0.0461 (5) | |
C11 | 1.0676 (3) | 0.79469 (18) | 0.73120 (8) | 0.0506 (5) | |
H11A | 0.9940 | 0.8668 | 0.7341 | 0.061* | |
H11B | 1.1869 | 0.8057 | 0.7055 | 0.061* | |
C12 | 1.1488 (3) | 0.76146 (18) | 0.79171 (9) | 0.0500 (5) | |
H12A | 1.2393 | 0.6953 | 0.7886 | 0.060* | |
H12B | 1.2309 | 0.8235 | 0.8078 | 0.060* | |
C13 | 0.9649 (3) | 0.73475 (15) | 0.83207 (8) | 0.0431 (5) | |
C14 | 0.8354 (3) | 0.63945 (16) | 0.80305 (8) | 0.0437 (4) | |
H14 | 0.9376 | 0.5799 | 0.7934 | 0.052* | |
C15 | 0.7042 (4) | 0.5901 (2) | 0.85305 (9) | 0.0614 (6) | |
H15A | 0.5775 | 0.6341 | 0.8598 | 0.074* | |
H15B | 0.6674 | 0.5111 | 0.8462 | 0.074* | |
C16 | 0.8584 (4) | 0.60245 (19) | 0.90194 (9) | 0.0605 (6) | |
H16 | 0.8498 | 0.5619 | 0.9366 | 0.073* | |
C17 | 1.0091 (4) | 0.67786 (17) | 0.89034 (8) | 0.0491 (5) | |
C18 | 1.1800 (4) | 0.7120 (2) | 0.92989 (9) | 0.0596 (6) | |
C19 | 1.2148 (5) | 0.6444 (3) | 0.98430 (10) | 0.0841 (9) | |
H19A | 1.3263 | 0.6782 | 1.0065 | 0.126* | |
H19B | 1.2521 | 0.5677 | 0.9743 | 0.126* | |
H19C | 1.0882 | 0.6439 | 1.0070 | 0.126* | |
C20 | 0.8361 (4) | 0.84353 (17) | 0.84474 (9) | 0.0583 (6) | |
H20A | 0.9170 | 0.8938 | 0.8689 | 0.087* | |
H20B | 0.7084 | 0.8233 | 0.8644 | 0.087* | |
H20C | 0.8031 | 0.8811 | 0.8088 | 0.087* | |
C21 | 0.7052 (4) | 0.85114 (18) | 0.64361 (10) | 0.0650 (7) | |
H21A | 0.6380 | 0.8624 | 0.6067 | 0.098* | |
H21B | 0.7956 | 0.9146 | 0.6518 | 0.098* | |
H21C | 0.6004 | 0.8451 | 0.6735 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1292 (18) | 0.1085 (15) | 0.0636 (11) | 0.0078 (15) | 0.0199 (12) | −0.0263 (10) |
O2 | 0.0872 (14) | 0.0929 (13) | 0.0717 (11) | −0.0241 (13) | −0.0179 (10) | 0.0001 (10) |
C1 | 0.0630 (14) | 0.0734 (15) | 0.0493 (11) | −0.0159 (13) | −0.0024 (11) | 0.0101 (11) |
C2 | 0.0675 (16) | 0.0992 (19) | 0.0502 (12) | −0.0030 (16) | 0.0145 (12) | 0.0093 (13) |
C3 | 0.0827 (18) | 0.0691 (15) | 0.0532 (13) | 0.0111 (15) | 0.0042 (13) | −0.0050 (11) |
C4 | 0.0750 (16) | 0.0569 (13) | 0.0555 (13) | −0.0038 (13) | −0.0047 (12) | −0.0082 (11) |
C5 | 0.0515 (12) | 0.0496 (11) | 0.0492 (11) | 0.0004 (10) | −0.0050 (10) | −0.0017 (9) |
C6 | 0.0530 (13) | 0.0698 (14) | 0.0623 (13) | −0.0163 (12) | −0.0024 (11) | −0.0081 (11) |
C7 | 0.0536 (13) | 0.0549 (12) | 0.0568 (12) | −0.0154 (11) | 0.0062 (11) | −0.0041 (10) |
C8 | 0.0406 (10) | 0.0383 (9) | 0.0495 (10) | 0.0017 (8) | 0.0049 (9) | −0.0015 (8) |
C9 | 0.0394 (10) | 0.0378 (9) | 0.0445 (9) | 0.0014 (8) | 0.0026 (8) | −0.0013 (8) |
C10 | 0.0500 (11) | 0.0430 (10) | 0.0454 (10) | −0.0014 (9) | 0.0001 (9) | −0.0007 (8) |
C11 | 0.0497 (12) | 0.0530 (11) | 0.0491 (10) | −0.0129 (10) | 0.0044 (9) | 0.0033 (9) |
C12 | 0.0463 (11) | 0.0536 (11) | 0.0500 (10) | −0.0088 (10) | −0.0002 (10) | −0.0008 (9) |
C13 | 0.0456 (11) | 0.0382 (10) | 0.0455 (10) | 0.0003 (9) | 0.0034 (9) | −0.0024 (8) |
C14 | 0.0454 (11) | 0.0385 (9) | 0.0473 (10) | −0.0009 (9) | 0.0058 (9) | 0.0005 (8) |
C15 | 0.0670 (14) | 0.0599 (13) | 0.0573 (13) | −0.0170 (12) | 0.0088 (12) | 0.0069 (10) |
C16 | 0.0737 (15) | 0.0613 (13) | 0.0464 (11) | −0.0033 (13) | 0.0053 (12) | 0.0078 (10) |
C17 | 0.0565 (12) | 0.0463 (11) | 0.0445 (10) | 0.0069 (10) | 0.0050 (10) | −0.0010 (9) |
C18 | 0.0605 (14) | 0.0669 (14) | 0.0514 (12) | 0.0079 (13) | −0.0024 (11) | −0.0064 (11) |
C19 | 0.091 (2) | 0.103 (2) | 0.0587 (14) | 0.0107 (19) | −0.0158 (15) | 0.0070 (14) |
C20 | 0.0707 (14) | 0.0453 (11) | 0.0588 (12) | 0.0101 (11) | 0.0014 (12) | −0.0061 (9) |
C21 | 0.0818 (17) | 0.0492 (12) | 0.0641 (13) | 0.0098 (13) | −0.0145 (13) | 0.0035 (10) |
O1—C3 | 1.226 (3) | C11—H11A | 0.9700 |
O2—C18 | 1.221 (3) | C11—H11B | 0.9700 |
C1—C2 | 1.326 (3) | C12—C13 | 1.526 (3) |
C1—C10 | 1.496 (3) | C12—H12A | 0.9700 |
C1—H1 | 0.9300 | C12—H12B | 0.9700 |
C2—C3 | 1.461 (4) | C13—C17 | 1.524 (3) |
C2—H2 | 0.9300 | C13—C14 | 1.542 (3) |
C3—C4 | 1.444 (4) | C13—C20 | 1.545 (3) |
C4—C5 | 1.332 (3) | C14—C15 | 1.535 (3) |
C4—H4 | 0.9300 | C14—H14 | 0.9800 |
C5—C6 | 1.500 (3) | C15—C16 | 1.499 (3) |
C5—C10 | 1.516 (3) | C15—H15A | 0.9700 |
C6—C7 | 1.520 (3) | C15—H15B | 0.9700 |
C6—H6A | 0.9700 | C16—C17 | 1.332 (3) |
C6—H6B | 0.9700 | C16—H16 | 0.9300 |
C7—C8 | 1.527 (3) | C17—C18 | 1.473 (3) |
C7—H7A | 0.9700 | C18—C19 | 1.499 (3) |
C7—H7B | 0.9700 | C19—H19A | 0.9599 |
C8—C14 | 1.515 (3) | C19—H19B | 0.9599 |
C8—C9 | 1.548 (3) | C19—H19C | 0.9599 |
C8—H8 | 0.9800 | C20—H20A | 0.9599 |
C9—C11 | 1.535 (3) | C20—H20B | 0.9599 |
C9—C10 | 1.576 (3) | C20—H20C | 0.9599 |
C9—H9 | 0.9800 | C21—H21A | 0.9599 |
C10—C21 | 1.553 (3) | C21—H21B | 0.9599 |
C11—C12 | 1.535 (3) | C21—H21C | 0.9599 |
C2—C1—C10 | 124.9 (2) | C13—C12—C11 | 110.24 (17) |
C2—C1—H1 | 117.6 | C13—C12—H12A | 109.6 |
C10—C1—H1 | 117.6 | C11—C12—H12A | 109.6 |
C1—C2—C3 | 121.6 (2) | C13—C12—H12B | 109.6 |
C1—C2—H2 | 119.2 | C11—C12—H12B | 109.6 |
C3—C2—H2 | 119.2 | H12A—C12—H12B | 108.1 |
O1—C3—C4 | 122.7 (3) | C17—C13—C12 | 118.94 (18) |
O1—C3—C2 | 121.5 (3) | C17—C13—C14 | 99.28 (15) |
C4—C3—C2 | 115.8 (2) | C12—C13—C14 | 107.19 (15) |
C5—C4—C3 | 123.6 (2) | C17—C13—C20 | 107.12 (15) |
C5—C4—H4 | 118.2 | C12—C13—C20 | 110.57 (16) |
C3—C4—H4 | 118.2 | C14—C13—C20 | 113.46 (17) |
C4—C5—C6 | 121.2 (2) | C8—C14—C15 | 122.14 (18) |
C4—C5—C10 | 122.5 (2) | C8—C14—C13 | 113.99 (15) |
C6—C5—C10 | 116.17 (17) | C15—C14—C13 | 103.89 (15) |
C5—C6—C7 | 110.57 (19) | C8—C14—H14 | 105.1 |
C5—C6—H6A | 109.5 | C15—C14—H14 | 105.1 |
C7—C6—H6A | 109.5 | C13—C14—H14 | 105.1 |
C5—C6—H6B | 109.5 | C16—C15—C14 | 99.80 (18) |
C7—C6—H6B | 109.5 | C16—C15—H15A | 111.8 |
H6A—C6—H6B | 108.1 | C14—C15—H15A | 111.8 |
C6—C7—C8 | 111.90 (17) | C16—C15—H15B | 111.8 |
C6—C7—H7A | 109.2 | C14—C15—H15B | 111.8 |
C8—C7—H7A | 109.2 | H15A—C15—H15B | 109.5 |
C6—C7—H7B | 109.2 | C17—C16—C15 | 112.64 (18) |
C8—C7—H7B | 109.2 | C17—C16—H16 | 123.7 |
H7A—C7—H7B | 107.9 | C15—C16—H16 | 123.7 |
C14—C8—C7 | 111.90 (16) | C16—C17—C18 | 126.1 (2) |
C14—C8—C9 | 107.43 (16) | C16—C17—C13 | 109.56 (19) |
C7—C8—C9 | 110.53 (15) | C18—C17—C13 | 124.0 (2) |
C14—C8—H8 | 109.0 | O2—C18—C17 | 120.5 (2) |
C7—C8—H8 | 109.0 | O2—C18—C19 | 120.8 (2) |
C9—C8—H8 | 109.0 | C17—C18—C19 | 118.7 (2) |
C11—C9—C8 | 112.10 (15) | C18—C19—H19A | 109.5 |
C11—C9—C10 | 113.81 (16) | C18—C19—H19B | 109.5 |
C8—C9—C10 | 112.09 (16) | H19A—C19—H19B | 109.5 |
C11—C9—H9 | 106.0 | C18—C19—H19C | 109.5 |
C8—C9—H9 | 106.0 | H19A—C19—H19C | 109.5 |
C10—C9—H9 | 106.0 | H19B—C19—H19C | 109.5 |
C1—C10—C5 | 111.39 (17) | C13—C20—H20A | 109.5 |
C1—C10—C21 | 107.31 (18) | C13—C20—H20B | 109.5 |
C5—C10—C21 | 109.50 (18) | H20A—C20—H20B | 109.5 |
C1—C10—C9 | 109.97 (17) | C13—C20—H20C | 109.5 |
C5—C10—C9 | 107.24 (15) | H20A—C20—H20C | 109.5 |
C21—C10—C9 | 111.48 (16) | H20B—C20—H20C | 109.5 |
C9—C11—C12 | 113.82 (16) | C10—C21—H21A | 109.5 |
C9—C11—H11A | 108.8 | C10—C21—H21B | 109.5 |
C12—C11—H11A | 108.8 | H21A—C21—H21B | 109.5 |
C9—C11—H11B | 108.8 | C10—C21—H21C | 109.5 |
C12—C11—H11B | 108.8 | H21A—C21—H21C | 109.5 |
H11A—C11—H11B | 107.7 | H21B—C21—H21C | 109.5 |
C10—C1—C2—C3 | 1.2 (4) | C8—C9—C11—C12 | 51.8 (2) |
C1—C2—C3—O1 | 174.3 (3) | C10—C9—C11—C12 | −179.63 (17) |
C1—C2—C3—C4 | −4.4 (4) | C9—C11—C12—C13 | −54.3 (2) |
O1—C3—C4—C5 | −174.4 (3) | C11—C12—C13—C17 | 168.19 (16) |
C2—C3—C4—C5 | 4.3 (4) | C11—C12—C13—C14 | 56.8 (2) |
C3—C4—C5—C6 | −178.0 (2) | C11—C12—C13—C20 | −67.3 (2) |
C3—C4—C5—C10 | −1.0 (4) | C7—C8—C14—C15 | −52.3 (2) |
C4—C5—C6—C7 | 121.5 (2) | C9—C8—C14—C15 | −173.83 (17) |
C10—C5—C6—C7 | −55.8 (3) | C7—C8—C14—C13 | −178.48 (16) |
C5—C6—C7—C8 | 54.0 (3) | C9—C8—C14—C13 | 60.0 (2) |
C6—C7—C8—C14 | −175.12 (18) | C17—C13—C14—C8 | 172.40 (16) |
C6—C7—C8—C9 | −55.4 (2) | C12—C13—C14—C8 | −63.3 (2) |
C14—C8—C9—C11 | −52.2 (2) | C20—C13—C14—C8 | 59.1 (2) |
C7—C8—C9—C11 | −174.52 (17) | C17—C13—C14—C15 | 37.2 (2) |
C14—C8—C9—C10 | 178.41 (15) | C12—C13—C14—C15 | 161.49 (17) |
C7—C8—C9—C10 | 56.1 (2) | C20—C13—C14—C15 | −76.2 (2) |
C2—C1—C10—C5 | 2.1 (3) | C8—C14—C15—C16 | −165.34 (18) |
C2—C1—C10—C21 | −117.7 (3) | C13—C14—C15—C16 | −34.8 (2) |
C2—C1—C10—C9 | 120.9 (2) | C14—C15—C16—C17 | 19.4 (3) |
C4—C5—C10—C1 | −2.3 (3) | C15—C16—C17—C18 | 178.0 (2) |
C6—C5—C10—C1 | 174.97 (18) | C15—C16—C17—C13 | 4.5 (3) |
C4—C5—C10—C21 | 116.3 (2) | C12—C13—C17—C16 | −141.8 (2) |
C6—C5—C10—C21 | −66.5 (2) | C14—C13—C17—C16 | −26.2 (2) |
C4—C5—C10—C9 | −122.6 (2) | C20—C13—C17—C16 | 92.0 (2) |
C6—C5—C10—C9 | 54.6 (2) | C12—C13—C17—C18 | 44.5 (3) |
C11—C9—C10—C1 | 56.5 (2) | C14—C13—C17—C18 | 160.17 (19) |
C8—C9—C10—C1 | −174.94 (16) | C20—C13—C17—C18 | −81.6 (2) |
C11—C9—C10—C5 | 177.80 (16) | C16—C17—C18—O2 | −168.9 (2) |
C8—C9—C10—C5 | −53.7 (2) | C13—C17—C18—O2 | 3.7 (3) |
C11—C9—C10—C21 | −62.4 (2) | C16—C17—C18—C19 | 11.1 (3) |
C8—C9—C10—C21 | 66.2 (2) | C13—C17—C18—C19 | −176.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12B···O2 | 0.97 | 2.60 | 3.076 (3) | 111 |
C19—H19B···O1i | 0.96 | 2.57 | 3.356 (4) | 139 |
C21—H21A···O1ii | 0.96 | 2.59 | 3.537 (3) | 169 |
Symmetry codes: (i) −x+5/2, −y+1, z+1/2; (ii) x−1/2, −y+3/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C21H26O2 |
Mr | 310.42 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 6.3625 (12), 11.745 (2), 23.007 (4) |
V (Å3) | 1719.2 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.25 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.981, 0.999 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10912, 2274, 1871 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.102, 1.05 |
No. of reflections | 2274 |
No. of parameters | 212 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.13 |
Absolute structure | See text |
Computer programs: APEX2 (Bruker, ????), SAINT (Bruker, 2003), SAINT, SHELXTL (Bruker, 2003), SHELXTL, PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19B···O1i | 0.96 | 2.57 | 3.356 (4) | 139 |
C21—H21A···O1ii | 0.96 | 2.59 | 3.537 (3) | 169 |
Symmetry codes: (i) −x+5/2, −y+1, z+1/2; (ii) x−1/2, −y+3/2, −z+1. |
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The title compound, (I), is used in the synthesis of prednisolone, because the ring A is fully functionalized a 1,4-dien-3-one system (Nitta et al., 1985). We present here its crystal structure, which exhibits the crystal packing close to those observed in 17α-hydroxy-4-pregnen-20-yn-3-one (II) (Reisch et al., 1993) and 17α-hydroxypregna-1,4-diene-3,20-dione (III) (Sheng et al., 2007). In (I) (Fig. 1), all bond lengths and angles agree with those in (II) and (III). The C1═C2, C4═C5, C16═C17, O1—C3 and O2—C18 distances are 1.326 (3) Å, 1.332 (3) Å, 1.332 (3) Å, 1.226 (3) Å and 1.221 (2) Å, respectively.
Ring A and atoms O1 and C6 are almost coplanar with the r.m.s. deviation of 0.061 (1) Å. Rings B and C show normal chair conformations, which are very similar to those reported by Xia et al. (2005). Ring D has an envelope conformation with atom C14 deviating at 0.589 (3) Å from the mean plane C13/C15/C16/C17 [in spite of structures (II) and (III) with the most deviating atom C13].
In the crystal, the weak intermolecular C—H···O hydrogen bonds (Table 1) stabilize the packing (Fig. 2).