organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

21-Hy­dr­oxy­pregna-1,4-diene-3,20-dione

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 27 March 2011; accepted 17 July 2011; online 23 July 2011)

The title compound, C21H28O3, is a fungal transformed metabolite of decoxycorticosterone acetate, consisting of four fused rings A, B, C and D. Ring A is nearly planar, with a maximum deviation of 0.010 (3) Å from the least-squares plane, while the trans-fused rings B and C adopt chair conformations. The five-membered ring D is in an envelope conformation. The orientation of the side chain is stabilized by an intramolecular O—H⋯O hydrogen bond. In the crystal, adjecent mol­ecules are linked by C—H⋯O hydrogen bonds into extended zigzag chains along the a axis.

Related literature

The title compound was previously reported as the transformed metabolite of 11-de­oxy­corticosterone, see: Holland et al. (1995[Holland, H. L., Nguyen, D. H. & Pearson, N. M. (1995). Steroids, 60, 646-649.]). For the crystal structure of the closely related compound corticosterone, see: Campsteyn et al. (1973[Campsteyn, H., Dupont, L., Dideberg, O. & Mandel, N. (1973). Acta Cryst. B29, 1726-1728.]) and for that of of 11-de­oxy­corticosterone, see: Dideberg et al. (1973[Dideberg, O., Campsteyn, H. & Dupont, L. (1973). Acta Cryst. B29, 103-112.]); Dey et al. (1999[Dey, R., Roychowdhury, S., Roychowdhury, P. & Righi, L. (1999). J. Chem. Crystallogr. 29, 1271-1275.]).

[Scheme 1]

Experimental

Crystal data
  • C21H28O3

  • Mr = 328.43

  • Monoclinic, P 21

  • a = 7.5882 (9) Å

  • b = 11.3506 (13) Å

  • c = 10.5462 (12) Å

  • β = 102.258 (2)°

  • V = 887.64 (18) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.36 × 0.13 × 0.12 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.990

  • 5287 measured reflections

  • 1739 independent reflections

  • 1467 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.107

  • S = 0.95

  • 1739 reflections

  • 219 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H1O2⋯O3 0.91 1.98 2.602 (4) 124
C21—H22B⋯O1i 0.97 2.53 3.415 (5) 152
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Structural modification of a substance as a result of enzymatic or metabolic activities of a living organism is known as biotransformation. In the current biotransformational study, the structural modification of a hypertension- inducing agent, 21-hydroxyprogesterone-21-acetate also known as 11-decoxycorticosterone acetate (DOCA), was investigated by using Cunninghamella elegans to obtain the title compound, 21-hydyoxypregna-1,4-diene-3,20-dione (I) as transformed metabolite, previously obtained as a result of the biotransformation of deoxycorticosteroid [Holland et al., 1995]. The title compound posseses four fused rings A (C1–C5/C10), B (C5–C10), C (C8–C9/C11–C14) and D (C13–C17). Trans fused rings B [Q= 0.568 (3) Å, θ = 177.5 (3)° and ϕ = 259 (13)°]and C [Q= 0.576 (3) Å, θ = 173.4 (3)° and ϕ = 97 (2)°] are in chair conformations, whereas ring D adopts [Q= 0.444 (3)Å and ϕ = 10.6 (4)°] an envelope conformation. Ring A found Planar in geometery. The conformation of the acetyl side on C17 is stabilized by intramolecular O2–H1O2···O3 hydrogen bonding (Fig.1). In the crystal structure, the molecules are linked by C21–H22B···O1 interaction to form extended chains in a zigzag fashion (Fig. 2, Table-1). The bond dimensions are similar to those found in structurally related corticosterone [Campsteyn et al. 1973] and 11-deoxycorticosterone (Dey et al., 1999 and Dideberg et al., 1973).

Related literature top

The title compound was previously reported as the transformed metabolite of 11-deoxycorticosterone, see: Holland et al. (1995). For the crystal structure of the closely related compound corticosterone, see: Campsteyn et al. (1973) and for that of of 11-deoxycorticosterone, see: Dideberg et al. (1973); Dey et al. (1999).

Experimental top

Fungal medium was prepared by dissolving following ingredients in distilled H2O (4.0 L): glucose (40.0 g), glycerol (40.0 ml), peptone (20.0 g), potassium dihydrogen phosphate (20.0 g), and sodium chloride (20.0 g), yeast extract (20.0 g) and equally distributed in 40 conical flasks (100 ml per flask). The mouth of flasks were covered with cotton wool and autoclaved at 121 °C. The mycelia of Cunninghamella elegans (NRRL 1392) were transferred into flasks and incubated at 26 °C for three days on rotary shaker. After growth of C. elegans, 21-hydroxyprogesterone-21-acetate (1 g m, dissolved in 20 ml acetone, 0.5 ml per flask) was distributed in all the flasks and allow to grow under same conditions for 14 days, followed by the filtration and extraction with dichloromethane. The extract was dried over anhydrous sodium sulfate and evaporated to obtained brown gumy material. The gummy material was fractionated by using silica gel column chromatography (gradient petroleum ether-acetone solvent system) to obtain several fractions. The fraction obtained 25%. was finally purified by using RP-HPLC (L-80, methanol-water 2:1, retention time 32 min.) to obtain title compound (15 mg).

Refinement top

H atoms on methyl, methylene, methine and oxygen were positioned geometrically with C—H = 0.96 Å, 0.97 Å, 0.93 Å and O—H = 0.90 Å respectively, and constrained to ride on their parent atoms with Uiso(H)= 1.2Ueq(CH2, CH and OH) and 1.5Ueq(CH3). The absolute configuration was assumed to be that of corticosterone (Campsteyn et al., 1973) and 11-decoxycorticosterone (Diberg et al., 1973) & Dey et al., 1999) itself; 1538 Friedel pairs were merged.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 30% probability level. The dashed lines indicates the intramolecular hydrogen bonds. Hydrogen atoms are omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of the title compound I. Only hydrogen atoms involved in hydrogen bonding are shown.
21-Hydroxypregna-1,4-diene-3,20-dione top
Crystal data top
C21H28O3F(000) = 356
Mr = 328.43Dx = 1.229 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.5882 (9) ÅCell parameters from 1378 reflections
b = 11.3506 (13) Åθ = 2.0–25.5°
c = 10.5462 (12) ŵ = 0.08 mm1
β = 102.258 (2)°T = 298 K
V = 887.64 (18) Å3Block, colourless
Z = 20.36 × 0.13 × 0.12 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1739 independent reflections
Radiation source: fine-focus sealed tube1467 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 8.33 pixels mm-1θmax = 25.5°, θmin = 2.0°
ω scanh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1313
Tmin = 0.972, Tmax = 0.990l = 812
5287 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0661P)2 + 0.090P]
where P = (Fo2 + 2Fc2)/3
1739 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.14 e Å3
1 restraintΔρmin = 0.13 e Å3
Crystal data top
C21H28O3V = 887.64 (18) Å3
Mr = 328.43Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.5882 (9) ŵ = 0.08 mm1
b = 11.3506 (13) ÅT = 298 K
c = 10.5462 (12) Å0.36 × 0.13 × 0.12 mm
β = 102.258 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1739 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1467 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.990Rint = 0.026
5287 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.107H-atom parameters constrained
S = 0.95Δρmax = 0.14 e Å3
1739 reflectionsΔρmin = 0.13 e Å3
219 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
xyzUiso*/Ueq
O10.5573 (4)0.6466 (3)0.9017 (2)0.0945 (9)
O20.2867 (4)0.3644 (3)0.2454 (2)0.0913 (9)
H1O20.18950.40960.27880.110*
O30.0016 (3)0.4543 (3)0.1825 (2)0.0826 (9)
C10.5718 (4)0.6862 (3)0.5714 (3)0.0618 (9)
H1A0.65790.68700.52030.074*
C20.6286 (4)0.6644 (4)0.6965 (3)0.0685 (10)
H2A0.75040.64970.72890.082*
C30.5054 (4)0.6630 (3)0.7843 (3)0.0629 (8)
C40.3171 (4)0.6834 (3)0.7260 (3)0.0567 (8)
H4A0.23380.68200.77910.068*
C50.2577 (4)0.7042 (3)0.5998 (3)0.0454 (7)
C60.0594 (4)0.7164 (3)0.5427 (3)0.0587 (8)
H6A0.03510.79270.50110.070*
H6B0.00860.71060.61070.070*
C70.0023 (4)0.6184 (3)0.4432 (3)0.0543 (8)
H7A0.01650.54280.48700.065*
H7B0.12410.62790.40270.065*
C80.1135 (3)0.6197 (2)0.3392 (2)0.0374 (6)
H8A0.09150.69470.29240.045*
C90.3169 (3)0.6114 (2)0.4003 (2)0.0391 (6)
H9A0.33450.53600.44650.047*
C100.3807 (3)0.7096 (3)0.5053 (2)0.0441 (7)
C110.4304 (4)0.6053 (3)0.2956 (3)0.0520 (8)
H11A0.42620.68140.25320.062*
H11B0.55490.58980.33730.062*
C120.3677 (3)0.5108 (3)0.1926 (3)0.0496 (7)
H12A0.43740.51690.12570.059*
H12B0.38890.43350.23200.059*
C130.1683 (3)0.5243 (2)0.1315 (2)0.0374 (6)
C140.0637 (3)0.5206 (2)0.2418 (2)0.0371 (6)
H14A0.09890.44720.28940.045*
C150.1335 (4)0.5052 (3)0.1719 (3)0.0515 (7)
H15A0.20190.46570.22730.062*
H15B0.18890.58090.14600.062*
C160.1246 (4)0.4299 (3)0.0534 (3)0.0572 (8)
H16A0.19280.46670.02480.069*
H16B0.17480.35240.06170.069*
C170.0763 (3)0.4196 (3)0.0464 (2)0.0442 (6)
H17A0.12330.34600.08930.053*
C180.1330 (5)0.6381 (3)0.0533 (3)0.0561 (8)
H18A0.16030.70440.11060.084*
H18B0.00860.64120.00940.084*
H18C0.20800.64030.00940.084*
C190.3717 (5)0.8342 (3)0.4439 (3)0.0665 (9)
H19A0.39050.89250.51130.100*
H19B0.25540.84570.38810.100*
H19C0.46350.84150.39430.100*
C200.1086 (4)0.4173 (3)0.0904 (3)0.0487 (7)
C210.2832 (5)0.3690 (4)0.1131 (3)0.0672 (9)
H22A0.38170.41810.06850.081*
H22B0.30130.29030.07670.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.104 (2)0.128 (2)0.0422 (12)0.0043 (19)0.0030 (12)0.0045 (16)
O20.1074 (19)0.113 (2)0.0626 (15)0.0171 (18)0.0394 (14)0.0185 (16)
O30.0769 (16)0.123 (2)0.0423 (11)0.0197 (15)0.0010 (11)0.0080 (13)
C10.0358 (13)0.100 (3)0.0503 (17)0.0076 (16)0.0113 (13)0.0282 (18)
C20.0459 (16)0.100 (3)0.0544 (18)0.0067 (18)0.0006 (15)0.022 (2)
C30.072 (2)0.072 (2)0.0398 (15)0.0014 (18)0.0019 (15)0.0067 (16)
C40.0578 (16)0.079 (2)0.0381 (14)0.0107 (16)0.0206 (13)0.0129 (15)
C50.0430 (13)0.0529 (17)0.0418 (14)0.0062 (12)0.0127 (12)0.0123 (13)
C60.0418 (14)0.086 (2)0.0511 (17)0.0021 (15)0.0167 (13)0.0210 (17)
C70.0346 (13)0.079 (2)0.0510 (16)0.0073 (14)0.0138 (12)0.0163 (16)
C80.0332 (12)0.0424 (14)0.0374 (12)0.0011 (11)0.0091 (10)0.0030 (11)
C90.0343 (12)0.0466 (14)0.0378 (13)0.0019 (11)0.0111 (11)0.0039 (12)
C100.0390 (13)0.0617 (18)0.0338 (13)0.0067 (12)0.0130 (11)0.0076 (13)
C110.0353 (13)0.081 (2)0.0430 (14)0.0117 (13)0.0161 (12)0.0176 (15)
C120.0365 (14)0.072 (2)0.0435 (14)0.0019 (13)0.0164 (12)0.0132 (15)
C130.0384 (13)0.0406 (14)0.0347 (12)0.0018 (11)0.0115 (11)0.0028 (12)
C140.0350 (13)0.0384 (13)0.0383 (13)0.0001 (10)0.0086 (11)0.0010 (11)
C150.0371 (14)0.0630 (19)0.0541 (16)0.0042 (13)0.0093 (12)0.0162 (15)
C160.0489 (15)0.0660 (19)0.0572 (17)0.0109 (15)0.0126 (14)0.0192 (16)
C170.0481 (14)0.0418 (14)0.0423 (14)0.0010 (13)0.0089 (12)0.0069 (13)
C180.083 (2)0.0443 (16)0.0436 (15)0.0050 (15)0.0185 (14)0.0006 (13)
C190.085 (2)0.061 (2)0.0556 (19)0.0246 (18)0.0177 (17)0.0115 (16)
C200.0550 (15)0.0485 (16)0.0416 (14)0.0026 (14)0.0079 (13)0.0127 (13)
C210.075 (2)0.074 (2)0.0573 (19)0.0070 (18)0.0232 (16)0.0122 (17)
Geometric parameters (Å, º) top
O1—C31.231 (4)C11—H11A0.9700
O2—C211.402 (4)C11—H11B0.9700
O2—H1O20.9067C12—C131.522 (4)
O3—C201.202 (3)C12—H12A0.9700
C1—C21.321 (4)C12—H12B0.9700
C1—C101.493 (4)C13—C181.525 (4)
C1—H1A0.9300C13—C141.542 (3)
C2—C31.450 (5)C13—C171.562 (4)
C2—H2A0.9300C14—C151.531 (3)
C3—C41.450 (4)C14—H14A0.9800
C4—C51.332 (4)C15—C161.528 (4)
C4—H4A0.9300C15—H15A0.9700
C5—C61.504 (4)C15—H15B0.9700
C5—C101.505 (4)C16—C171.546 (4)
C6—C71.527 (4)C16—H16A0.9700
C6—H6A0.9700C16—H16B0.9700
C6—H6B0.9700C17—C201.514 (4)
C7—C81.519 (4)C17—H17A0.9800
C7—H7A0.9700C18—H18A0.9600
C7—H7B0.9700C18—H18B0.9600
C8—C141.517 (3)C18—H18C0.9600
C8—C91.544 (3)C19—H19A0.9600
C8—H8A0.9800C19—H19B0.9600
C9—C111.539 (3)C19—H19C0.9600
C9—C101.574 (4)C20—C211.500 (4)
C9—H9A0.9800C21—H22A0.9700
C10—C191.551 (5)C21—H22B0.9700
C11—C121.528 (4)
C21—O2—H1O2100.3C13—C12—H12B109.4
C2—C1—C10125.3 (3)C11—C12—H12B109.4
C2—C1—H1A117.4H12A—C12—H12B108.0
C10—C1—H1A117.4C12—C13—C18111.0 (2)
C1—C2—C3121.5 (3)C12—C13—C14107.63 (19)
C1—C2—H2A119.2C18—C13—C14111.8 (2)
C3—C2—H2A119.2C12—C13—C17116.7 (2)
O1—C3—C2122.2 (3)C18—C13—C17109.15 (19)
O1—C3—C4121.8 (3)C14—C13—C17100.0 (2)
C2—C3—C4116.0 (2)C8—C14—C15119.2 (2)
C5—C4—C3123.1 (3)C8—C14—C13113.4 (2)
C5—C4—H4A118.4C15—C14—C13104.29 (19)
C3—C4—H4A118.4C8—C14—H14A106.4
C4—C5—C6120.9 (3)C15—C14—H14A106.4
C4—C5—C10122.9 (2)C13—C14—H14A106.4
C6—C5—C10116.1 (2)C16—C15—C14104.4 (2)
C5—C6—C7108.8 (2)C16—C15—H15A110.9
C5—C6—H6A109.9C14—C15—H15A110.9
C7—C6—H6A109.9C16—C15—H15B110.9
C5—C6—H6B109.9C14—C15—H15B110.9
C7—C6—H6B109.9H15A—C15—H15B108.9
H6A—C6—H6B108.3C15—C16—C17107.3 (2)
C8—C7—C6111.6 (2)C15—C16—H16A110.3
C8—C7—H7A109.3C17—C16—H16A110.3
C6—C7—H7A109.3C15—C16—H16B110.3
C8—C7—H7B109.3C17—C16—H16B110.3
C6—C7—H7B109.3H16A—C16—H16B108.5
H7A—C7—H7B108.0C20—C17—C16114.0 (2)
C14—C8—C7112.6 (2)C20—C17—C13114.7 (2)
C14—C8—C9108.66 (19)C16—C17—C13103.9 (2)
C7—C8—C9111.0 (2)C20—C17—H17A108.0
C14—C8—H8A108.1C16—C17—H17A108.0
C7—C8—H8A108.1C13—C17—H17A108.0
C9—C8—H8A108.1C13—C18—H18A109.5
C11—C9—C8111.5 (2)C13—C18—H18B109.5
C11—C9—C10113.7 (2)H18A—C18—H18B109.5
C8—C9—C10112.4 (2)C13—C18—H18C109.5
C11—C9—H9A106.2H18A—C18—H18C109.5
C8—C9—H9A106.2H18B—C18—H18C109.5
C10—C9—H9A106.2C10—C19—H19A109.5
C1—C10—C5111.2 (2)C10—C19—H19B109.5
C1—C10—C19108.0 (3)H19A—C19—H19B109.5
C5—C10—C19109.6 (2)C10—C19—H19C109.5
C1—C10—C9109.0 (2)H19A—C19—H19C109.5
C5—C10—C9107.2 (2)H19B—C19—H19C109.5
C19—C10—C9111.9 (2)O3—C20—C21117.8 (3)
C12—C11—C9113.8 (2)O3—C20—C17123.1 (3)
C12—C11—H11A108.8C21—C20—C17119.1 (3)
C9—C11—H11A108.8O2—C21—C20112.2 (3)
C12—C11—H11B108.8O2—C21—H22A109.2
C9—C11—H11B108.8C20—C21—H22A109.2
H11A—C11—H11B107.7O2—C21—H22B109.2
C13—C12—C11111.2 (2)C20—C21—H22B109.2
C13—C12—H12A109.4H22A—C21—H22B107.9
C11—C12—H12A109.4
C10—C1—C2—C30.9 (6)C10—C9—C11—C12179.4 (2)
C1—C2—C3—O1177.6 (4)C9—C11—C12—C1353.7 (3)
C1—C2—C3—C41.6 (6)C11—C12—C13—C1866.5 (3)
O1—C3—C4—C5178.4 (4)C11—C12—C13—C1456.2 (3)
C2—C3—C4—C50.9 (5)C11—C12—C13—C17167.6 (2)
C3—C4—C5—C6175.7 (3)C7—C8—C14—C1553.7 (3)
C3—C4—C5—C100.6 (5)C9—C8—C14—C15177.0 (2)
C4—C5—C6—C7117.8 (3)C7—C8—C14—C13177.0 (2)
C10—C5—C6—C758.7 (4)C9—C8—C14—C1359.6 (3)
C5—C6—C7—C856.2 (3)C12—C13—C14—C861.7 (3)
C6—C7—C8—C14178.0 (2)C18—C13—C14—C860.5 (3)
C6—C7—C8—C956.0 (3)C17—C13—C14—C8175.93 (19)
C14—C8—C9—C1152.3 (3)C12—C13—C14—C15167.1 (2)
C7—C8—C9—C11176.6 (2)C18—C13—C14—C1570.7 (3)
C14—C8—C9—C10178.8 (2)C17—C13—C14—C1544.7 (2)
C7—C8—C9—C1054.4 (3)C8—C14—C15—C16161.2 (3)
C2—C1—C10—C50.5 (5)C13—C14—C15—C1633.4 (3)
C2—C1—C10—C19119.7 (4)C14—C15—C16—C178.4 (3)
C2—C1—C10—C9118.5 (4)C15—C16—C17—C20144.8 (3)
C4—C5—C10—C11.3 (4)C15—C16—C17—C1319.3 (3)
C6—C5—C10—C1175.1 (3)C12—C13—C17—C2080.5 (3)
C4—C5—C10—C19118.0 (3)C18—C13—C17—C2046.4 (3)
C6—C5—C10—C1965.5 (3)C14—C13—C17—C20163.8 (2)
C4—C5—C10—C9120.4 (3)C12—C13—C17—C16154.4 (2)
C6—C5—C10—C956.1 (3)C18—C13—C17—C1678.8 (3)
C11—C9—C10—C159.5 (3)C14—C13—C17—C1638.7 (3)
C8—C9—C10—C1172.8 (2)C16—C17—C20—O321.1 (4)
C11—C9—C10—C5179.9 (2)C13—C17—C20—O398.5 (3)
C8—C9—C10—C552.3 (3)C16—C17—C20—C21160.2 (3)
C11—C9—C10—C1959.9 (3)C13—C17—C20—C2180.2 (3)
C8—C9—C10—C1967.8 (3)O3—C20—C21—O25.9 (5)
C8—C9—C11—C1251.2 (3)C17—C20—C21—O2175.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O30.911.982.602 (4)124
C21—H22B···O1i0.972.533.415 (5)152
Symmetry code: (i) x+1, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC21H28O3
Mr328.43
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)7.5882 (9), 11.3506 (13), 10.5462 (12)
β (°) 102.258 (2)
V3)887.64 (18)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.36 × 0.13 × 0.12
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.972, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
5287, 1739, 1467
Rint0.026
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.107, 0.95
No. of reflections1739
No. of parameters219
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.13

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O30.911.982.602 (4)124
C21—H22B···O1i0.972.533.415 (5)152
Symmetry code: (i) x+1, y1/2, z+1.
 

References

First citationBruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCampsteyn, H., Dupont, L., Dideberg, O. & Mandel, N. (1973). Acta Cryst. B29, 1726–1728.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationDey, R., Roychowdhury, S., Roychowdhury, P. & Righi, L. (1999). J. Chem. Crystallogr. 29, 1271–1275.  Web of Science CSD CrossRef CAS Google Scholar
First citationDideberg, O., Campsteyn, H. & Dupont, L. (1973). Acta Cryst. B29, 103–112.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationHolland, H. L., Nguyen, D. H. & Pearson, N. M. (1995). Steroids, 60, 646–649.  CrossRef CAS PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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