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

Yousuf, S.; Bibi, M.; Choudhary, M.I.

doi:10.1107/S1600536811028674

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2122

doi:10.1107/S1600536811028674

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

S. Yousuf,^a ^* M. Bibi ^a and M. I. Choudhary ^a

^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 ). 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

Crystal data

C₂₁H₂₈O₃
M_r = 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 ) T_min = 0.972, T_max = 0.990
5287 measured reflections
1739 independent reflections
1467 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811028674/zb2014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028674/zb2014Isup2.hkl

checkCIF report

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).

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

	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.
	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

C₂₁H₂₈O₃	F(000) = 356
M_r = 328.43	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.5882 (9) Å	Cell parameters from 1378 reflections
b = 11.3506 (13) Å	θ = 2.0–25.5°
c = 10.5462 (12) Å	µ = 0.08 mm⁻¹
β = 102.258 (2)°	T = 298 K
V = 887.64 (18) Å³	Block, colourless
Z = 2	0.36 × 0.13 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1739 independent reflections
Radiation source: fine-focus sealed tube	1467 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.5°, θ_min = 2.0°
ω scan	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −13→13
T_min = 0.972, T_max = 0.990	l = −8→12
5287 measured reflections

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0661P)² + 0.090P] where P = (F_o² + 2F_c²)/3
1739 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₁H₂₈O₃	V = 887.64 (18) Å³
M_r = 328.43	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.5882 (9) Å	µ = 0.08 mm⁻¹
b = 11.3506 (13) Å	T = 298 K
c = 10.5462 (12) Å	0.36 × 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)
T_min = 0.972, T_max = 0.990	R_int = 0.026
5287 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.107	H-atom parameters constrained
S = 0.95	Δρ_max = 0.14 e Å⁻³
1739 reflections	Δρ_min = −0.13 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	0.5573 (4)	0.6466 (3)	0.9017 (2)	0.0945 (9)
O2	0.2867 (4)	0.3644 (3)	−0.2454 (2)	0.0913 (9)
H1O2	0.1895	0.4096	−0.2788	0.110*
O3	0.0016 (3)	0.4543 (3)	−0.1825 (2)	0.0826 (9)
C1	0.5718 (4)	0.6862 (3)	0.5714 (3)	0.0618 (9)
H1A	0.6579	0.6870	0.5203	0.074*
C2	0.6286 (4)	0.6644 (4)	0.6965 (3)	0.0685 (10)
H2A	0.7504	0.6497	0.7289	0.082*
C3	0.5054 (4)	0.6630 (3)	0.7843 (3)	0.0629 (8)
C4	0.3171 (4)	0.6834 (3)	0.7260 (3)	0.0567 (8)
H4A	0.2338	0.6820	0.7791	0.068*
C5	0.2577 (4)	0.7042 (3)	0.5998 (3)	0.0454 (7)
C6	0.0594 (4)	0.7164 (3)	0.5427 (3)	0.0587 (8)
H6A	0.0351	0.7927	0.5011	0.070*
H6B	−0.0086	0.7106	0.6107	0.070*
C7	0.0023 (4)	0.6184 (3)	0.4432 (3)	0.0543 (8)
H7A	0.0165	0.5428	0.4870	0.065*
H7B	−0.1241	0.6279	0.4027	0.065*
C8	0.1135 (3)	0.6197 (2)	0.3392 (2)	0.0374 (6)
H8A	0.0915	0.6947	0.2924	0.045*
C9	0.3169 (3)	0.6114 (2)	0.4003 (2)	0.0391 (6)
H9A	0.3345	0.5360	0.4465	0.047*
C10	0.3807 (3)	0.7096 (3)	0.5053 (2)	0.0441 (7)
C11	0.4304 (4)	0.6053 (3)	0.2956 (3)	0.0520 (8)
H11A	0.4262	0.6814	0.2532	0.062*
H11B	0.5549	0.5898	0.3373	0.062*
C12	0.3677 (3)	0.5108 (3)	0.1926 (3)	0.0496 (7)
H12A	0.4374	0.5169	0.1257	0.059*
H12B	0.3889	0.4335	0.2320	0.059*
C13	0.1683 (3)	0.5243 (2)	0.1315 (2)	0.0374 (6)
C14	0.0637 (3)	0.5206 (2)	0.2418 (2)	0.0371 (6)
H14A	0.0989	0.4472	0.2894	0.045*
C15	−0.1335 (4)	0.5052 (3)	0.1719 (3)	0.0515 (7)
H15A	−0.2019	0.4657	0.2273	0.062*
H15B	−0.1889	0.5809	0.1460	0.062*
C16	−0.1246 (4)	0.4299 (3)	0.0534 (3)	0.0572 (8)
H16A	−0.1928	0.4667	−0.0248	0.069*
H16B	−0.1748	0.3524	0.0617	0.069*
C17	0.0763 (3)	0.4196 (3)	0.0464 (2)	0.0442 (6)
H17A	0.1233	0.3460	0.0893	0.053*
C18	0.1330 (5)	0.6381 (3)	0.0533 (3)	0.0561 (8)
H18A	0.1603	0.7044	0.1106	0.084*
H18B	0.0086	0.6412	0.0094	0.084*
H18C	0.2080	0.6403	−0.0094	0.084*
C19	0.3717 (5)	0.8342 (3)	0.4439 (3)	0.0665 (9)
H19A	0.3905	0.8925	0.5113	0.100*
H19B	0.2554	0.8457	0.3881	0.100*
H19C	0.4635	0.8415	0.3943	0.100*
C20	0.1086 (4)	0.4173 (3)	−0.0904 (3)	0.0487 (7)
C21	0.2832 (5)	0.3690 (4)	−0.1131 (3)	0.0672 (9)
H22A	0.3817	0.4181	−0.0685	0.081*
H22B	0.3013	0.2903	−0.0767	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.104 (2)	0.128 (2)	0.0422 (12)	0.0043 (19)	−0.0030 (12)	0.0045 (16)
O2	0.1074 (19)	0.113 (2)	0.0626 (15)	0.0171 (18)	0.0394 (14)	−0.0185 (16)
O3	0.0769 (16)	0.123 (2)	0.0423 (11)	0.0197 (15)	0.0010 (11)	−0.0080 (13)
C1	0.0358 (13)	0.100 (3)	0.0503 (17)	−0.0076 (16)	0.0113 (13)	−0.0282 (18)
C2	0.0459 (16)	0.100 (3)	0.0544 (18)	0.0067 (18)	−0.0006 (15)	−0.022 (2)
C3	0.072 (2)	0.072 (2)	0.0398 (15)	−0.0014 (18)	0.0019 (15)	−0.0067 (16)
C4	0.0578 (16)	0.079 (2)	0.0381 (14)	−0.0107 (16)	0.0206 (13)	−0.0129 (15)
C5	0.0430 (13)	0.0529 (17)	0.0418 (14)	−0.0062 (12)	0.0127 (12)	−0.0123 (13)
C6	0.0418 (14)	0.086 (2)	0.0511 (17)	0.0021 (15)	0.0167 (13)	−0.0210 (17)
C7	0.0346 (13)	0.079 (2)	0.0510 (16)	−0.0073 (14)	0.0138 (12)	−0.0163 (16)
C8	0.0332 (12)	0.0424 (14)	0.0374 (12)	0.0011 (11)	0.0091 (10)	−0.0030 (11)
C9	0.0343 (12)	0.0466 (14)	0.0378 (13)	−0.0019 (11)	0.0111 (11)	−0.0039 (12)
C10	0.0390 (13)	0.0617 (18)	0.0338 (13)	−0.0067 (12)	0.0130 (11)	−0.0076 (13)
C11	0.0353 (13)	0.081 (2)	0.0430 (14)	−0.0117 (13)	0.0161 (12)	−0.0176 (15)
C12	0.0365 (14)	0.072 (2)	0.0435 (14)	0.0019 (13)	0.0164 (12)	−0.0132 (15)
C13	0.0384 (13)	0.0406 (14)	0.0347 (12)	0.0018 (11)	0.0115 (11)	−0.0028 (12)
C14	0.0350 (13)	0.0384 (13)	0.0383 (13)	−0.0001 (10)	0.0086 (11)	0.0010 (11)
C15	0.0371 (14)	0.0630 (19)	0.0541 (16)	−0.0042 (13)	0.0093 (12)	−0.0162 (15)
C16	0.0489 (15)	0.0660 (19)	0.0572 (17)	−0.0109 (15)	0.0126 (14)	−0.0192 (16)
C17	0.0481 (14)	0.0418 (14)	0.0423 (14)	−0.0010 (13)	0.0089 (12)	−0.0069 (13)
C18	0.083 (2)	0.0443 (16)	0.0436 (15)	−0.0050 (15)	0.0185 (14)	−0.0006 (13)
C19	0.085 (2)	0.061 (2)	0.0556 (19)	−0.0246 (18)	0.0177 (17)	−0.0115 (16)
C20	0.0550 (15)	0.0485 (16)	0.0416 (14)	−0.0026 (14)	0.0079 (13)	−0.0127 (13)
C21	0.075 (2)	0.074 (2)	0.0573 (19)	0.0070 (18)	0.0232 (16)	−0.0122 (17)

Geometric parameters (Å, º) top

O1—C3	1.231 (4)	C11—H11A	0.9700
O2—C21	1.402 (4)	C11—H11B	0.9700
O2—H1O2	0.9067	C12—C13	1.522 (4)
O3—C20	1.202 (3)	C12—H12A	0.9700
C1—C2	1.321 (4)	C12—H12B	0.9700
C1—C10	1.493 (4)	C13—C18	1.525 (4)
C1—H1A	0.9300	C13—C14	1.542 (3)
C2—C3	1.450 (5)	C13—C17	1.562 (4)
C2—H2A	0.9300	C14—C15	1.531 (3)
C3—C4	1.450 (4)	C14—H14A	0.9800
C4—C5	1.332 (4)	C15—C16	1.528 (4)
C4—H4A	0.9300	C15—H15A	0.9700
C5—C6	1.504 (4)	C15—H15B	0.9700
C5—C10	1.505 (4)	C16—C17	1.546 (4)
C6—C7	1.527 (4)	C16—H16A	0.9700
C6—H6A	0.9700	C16—H16B	0.9700
C6—H6B	0.9700	C17—C20	1.514 (4)
C7—C8	1.519 (4)	C17—H17A	0.9800
C7—H7A	0.9700	C18—H18A	0.9600
C7—H7B	0.9700	C18—H18B	0.9600
C8—C14	1.517 (3)	C18—H18C	0.9600
C8—C9	1.544 (3)	C19—H19A	0.9600
C8—H8A	0.9800	C19—H19B	0.9600
C9—C11	1.539 (3)	C19—H19C	0.9600
C9—C10	1.574 (4)	C20—C21	1.500 (4)
C9—H9A	0.9800	C21—H22A	0.9700
C10—C19	1.551 (5)	C21—H22B	0.9700
C11—C12	1.528 (4)

C21—O2—H1O2	100.3	C13—C12—H12B	109.4
C2—C1—C10	125.3 (3)	C11—C12—H12B	109.4
C2—C1—H1A	117.4	H12A—C12—H12B	108.0
C10—C1—H1A	117.4	C12—C13—C18	111.0 (2)
C1—C2—C3	121.5 (3)	C12—C13—C14	107.63 (19)
C1—C2—H2A	119.2	C18—C13—C14	111.8 (2)
C3—C2—H2A	119.2	C12—C13—C17	116.7 (2)
O1—C3—C2	122.2 (3)	C18—C13—C17	109.15 (19)
O1—C3—C4	121.8 (3)	C14—C13—C17	100.0 (2)
C2—C3—C4	116.0 (2)	C8—C14—C15	119.2 (2)
C5—C4—C3	123.1 (3)	C8—C14—C13	113.4 (2)
C5—C4—H4A	118.4	C15—C14—C13	104.29 (19)
C3—C4—H4A	118.4	C8—C14—H14A	106.4
C4—C5—C6	120.9 (3)	C15—C14—H14A	106.4
C4—C5—C10	122.9 (2)	C13—C14—H14A	106.4
C6—C5—C10	116.1 (2)	C16—C15—C14	104.4 (2)
C5—C6—C7	108.8 (2)	C16—C15—H15A	110.9
C5—C6—H6A	109.9	C14—C15—H15A	110.9
C7—C6—H6A	109.9	C16—C15—H15B	110.9
C5—C6—H6B	109.9	C14—C15—H15B	110.9
C7—C6—H6B	109.9	H15A—C15—H15B	108.9
H6A—C6—H6B	108.3	C15—C16—C17	107.3 (2)
C8—C7—C6	111.6 (2)	C15—C16—H16A	110.3
C8—C7—H7A	109.3	C17—C16—H16A	110.3
C6—C7—H7A	109.3	C15—C16—H16B	110.3
C8—C7—H7B	109.3	C17—C16—H16B	110.3
C6—C7—H7B	109.3	H16A—C16—H16B	108.5
H7A—C7—H7B	108.0	C20—C17—C16	114.0 (2)
C14—C8—C7	112.6 (2)	C20—C17—C13	114.7 (2)
C14—C8—C9	108.66 (19)	C16—C17—C13	103.9 (2)
C7—C8—C9	111.0 (2)	C20—C17—H17A	108.0
C14—C8—H8A	108.1	C16—C17—H17A	108.0
C7—C8—H8A	108.1	C13—C17—H17A	108.0
C9—C8—H8A	108.1	C13—C18—H18A	109.5
C11—C9—C8	111.5 (2)	C13—C18—H18B	109.5
C11—C9—C10	113.7 (2)	H18A—C18—H18B	109.5
C8—C9—C10	112.4 (2)	C13—C18—H18C	109.5
C11—C9—H9A	106.2	H18A—C18—H18C	109.5
C8—C9—H9A	106.2	H18B—C18—H18C	109.5
C10—C9—H9A	106.2	C10—C19—H19A	109.5
C1—C10—C5	111.2 (2)	C10—C19—H19B	109.5
C1—C10—C19	108.0 (3)	H19A—C19—H19B	109.5
C5—C10—C19	109.6 (2)	C10—C19—H19C	109.5
C1—C10—C9	109.0 (2)	H19A—C19—H19C	109.5
C5—C10—C9	107.2 (2)	H19B—C19—H19C	109.5
C19—C10—C9	111.9 (2)	O3—C20—C21	117.8 (3)
C12—C11—C9	113.8 (2)	O3—C20—C17	123.1 (3)
C12—C11—H11A	108.8	C21—C20—C17	119.1 (3)
C9—C11—H11A	108.8	O2—C21—C20	112.2 (3)
C12—C11—H11B	108.8	O2—C21—H22A	109.2
C9—C11—H11B	108.8	C20—C21—H22A	109.2
H11A—C11—H11B	107.7	O2—C21—H22B	109.2
C13—C12—C11	111.2 (2)	C20—C21—H22B	109.2
C13—C12—H12A	109.4	H22A—C21—H22B	107.9
C11—C12—H12A	109.4

C10—C1—C2—C3	−0.9 (6)	C10—C9—C11—C12	−179.4 (2)
C1—C2—C3—O1	−177.6 (4)	C9—C11—C12—C13	53.7 (3)
C1—C2—C3—C4	1.6 (6)	C11—C12—C13—C18	66.5 (3)
O1—C3—C4—C5	178.4 (4)	C11—C12—C13—C14	−56.2 (3)
C2—C3—C4—C5	−0.9 (5)	C11—C12—C13—C17	−167.6 (2)
C3—C4—C5—C6	175.7 (3)	C7—C8—C14—C15	53.7 (3)
C3—C4—C5—C10	−0.6 (5)	C9—C8—C14—C15	177.0 (2)
C4—C5—C6—C7	−117.8 (3)	C7—C8—C14—C13	177.0 (2)
C10—C5—C6—C7	58.7 (4)	C9—C8—C14—C13	−59.6 (3)
C5—C6—C7—C8	−56.2 (3)	C12—C13—C14—C8	61.7 (3)
C6—C7—C8—C14	178.0 (2)	C18—C13—C14—C8	−60.5 (3)
C6—C7—C8—C9	56.0 (3)	C17—C13—C14—C8	−175.93 (19)
C14—C8—C9—C11	52.3 (3)	C12—C13—C14—C15	−167.1 (2)
C7—C8—C9—C11	176.6 (2)	C18—C13—C14—C15	70.7 (3)
C14—C8—C9—C10	−178.8 (2)	C17—C13—C14—C15	−44.7 (2)
C7—C8—C9—C10	−54.4 (3)	C8—C14—C15—C16	161.2 (3)
C2—C1—C10—C5	−0.5 (5)	C13—C14—C15—C16	33.4 (3)
C2—C1—C10—C19	119.7 (4)	C14—C15—C16—C17	−8.4 (3)
C2—C1—C10—C9	−118.5 (4)	C15—C16—C17—C20	−144.8 (3)
C4—C5—C10—C1	1.3 (4)	C15—C16—C17—C13	−19.3 (3)
C6—C5—C10—C1	−175.1 (3)	C12—C13—C17—C20	−80.5 (3)
C4—C5—C10—C19	−118.0 (3)	C18—C13—C17—C20	46.4 (3)
C6—C5—C10—C19	65.5 (3)	C14—C13—C17—C20	163.8 (2)
C4—C5—C10—C9	120.4 (3)	C12—C13—C17—C16	154.4 (2)
C6—C5—C10—C9	−56.1 (3)	C18—C13—C17—C16	−78.8 (3)
C11—C9—C10—C1	−59.5 (3)	C14—C13—C17—C16	38.7 (3)
C8—C9—C10—C1	172.8 (2)	C16—C17—C20—O3	21.1 (4)
C11—C9—C10—C5	−179.9 (2)	C13—C17—C20—O3	−98.5 (3)
C8—C9—C10—C5	52.3 (3)	C16—C17—C20—C21	−160.2 (3)
C11—C9—C10—C19	59.9 (3)	C13—C17—C20—C21	80.2 (3)
C8—C9—C10—C19	−67.8 (3)	O3—C20—C21—O2	−5.9 (5)
C8—C9—C11—C12	−51.2 (3)	C17—C20—C21—O2	175.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₈O₃
M_r	328.43
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	7.5882 (9), 11.3506 (13), 10.5462 (12)
β (°)	102.258 (2)
V (Å³)	887.64 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.36 × 0.13 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.972, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	5287, 1739, 1467
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.107, 0.95
No. of reflections	1739
No. of parameters	219
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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−1/2, −z+1.

References

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

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Volume 67| Part 8| August 2011| Page o2122

doi:10.1107/S1600536811028674

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