17β-Hy-droxy-17α-(hy-droxy-meth-yl)estr-4-en-3-one.

The title compound, C(19)H(28)O(3), the fungal-transformed metabolite of the steroid methyl-oestrenol contains four fused rings A, B, C and D. Ring A adopts a half-chair and the trans-fused rings B and C adopt chair confirmations; the five-membered D ring is folded like an envelope. In the crystal, adjacent mol-ecules are linked by O-H⋯O(carbon-yl) and O-H⋯O(hy-droxy) hydrogen bonds into a layer structure.

Related literature

For the synthesis, see: Hübner & Ponsold (1983 ▶); Ponsold et al. (1978a ▶,b ▶); Szilagyi et al. (1984 ▶). For the crystal structures of three modified17b-hy­droxy-3-oxo-17a-(halogen/pseudo­halogenometh­yl)-estra-4-ene progestagens, see: Beck et al. (1986a ▶,b ▶,c ▶).

Experimental

Crystal data

C19H28O3

M = 304.41

Orthorhombic,

a = 9.9696 (6) Å

b = 12.5858 (8) Å

c = 13.3968 (8) Å

V = 1680.97 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.35 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

11685 measured reflections

2203 independent reflections

1799 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 1.11

2203 reflections

207 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004033X/hb5675sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004033X/hb5675Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H28O3	F(000) = 664
Mr = 304.41	Dx = 1.203 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2043 reflections
a = 9.9696 (6) Å	θ = 2.5–21.3°
b = 12.5858 (8) Å	µ = 0.08 mm−1
c = 13.3968 (8) Å	T = 295 K
V = 1680.97 (18) Å3	Prism, colorless
Z = 4	0.35 × 0.20 × 0.10 mm

Bruker SMART APEX CCD diffractometer	1799 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
graphite	θmax = 27.5°, θmin = 2.2°
ω scans	h = −12→12
11685 measured reflections	k = −15→16
2203 independent reflections	l = −17→13

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.0486P] where P = (Fo2 + 2Fc2)/3
2203 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.19 e Å−3
2 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.5961 (3)	1.11961 (17)	1.13914 (18)	0.0682 (7)
O2	0.39264 (19)	0.32100 (16)	1.04677 (15)	0.0492 (5)
O3	0.6378 (2)	0.26561 (14)	0.97416 (16)	0.0462 (5)
C1	0.6147 (3)	0.8388 (2)	1.17666 (19)	0.0464 (7)
H1A	0.5176	0.8385	1.1722	0.056*
H1B	0.6408	0.7906	1.2297	0.056*
C2	0.6631 (3)	0.9507 (2)	1.2017 (2)	0.0506 (7)
H2A	0.6235	0.9734	1.2643	0.061*
H2B	0.7598	0.9503	1.2097	0.061*
C3	0.6256 (3)	1.0271 (2)	1.1211 (2)	0.0451 (6)
C4	0.6340 (3)	0.9862 (2)	1.0191 (2)	0.0420 (6)
H4	0.6185	1.0328	0.9666	0.050*
C5	0.6628 (2)	0.88515 (19)	0.99789 (19)	0.0356 (6)
C6	0.6928 (3)	0.8510 (2)	0.89256 (19)	0.0438 (7)
H6A	0.7893	0.8480	0.8839	0.053*
H6B	0.6584	0.9044	0.8471	0.053*
C7	0.6336 (3)	0.74360 (19)	0.86388 (19)	0.0445 (7)
H7A	0.6689	0.7220	0.7995	0.053*
H7B	0.5370	0.7499	0.8579	0.053*
C8	0.6673 (3)	0.65901 (18)	0.94171 (18)	0.0333 (5)
H8	0.7651	0.6532	0.9468	0.040*
C9	0.6117 (3)	0.69403 (18)	1.04371 (16)	0.0310 (5)
H9	0.5153	0.7064	1.0350	0.037*
C10	0.6743 (3)	0.80063 (18)	1.07782 (17)	0.0329 (5)
H10	0.7701	0.7879	1.0890	0.040*
C11	0.6269 (3)	0.60786 (18)	1.12419 (19)	0.0393 (6)
H11A	0.7209	0.6015	1.1418	0.047*
H11B	0.5785	0.6298	1.1835	0.047*
C12	0.5748 (3)	0.49914 (18)	1.09091 (16)	0.0342 (6)
H12A	0.5940	0.4470	1.1423	0.041*
H12B	0.4782	0.5026	1.0826	0.041*
C13	0.6389 (2)	0.46399 (18)	0.99316 (17)	0.0306 (5)
C14	0.6106 (3)	0.55026 (19)	0.91475 (17)	0.0336 (5)
H14	0.5129	0.5584	0.9116	0.040*
C15	0.6536 (4)	0.4988 (2)	0.8161 (2)	0.0542 (8)
H15A	0.7488	0.5087	0.8044	0.065*
H15B	0.6040	0.5285	0.7604	0.065*
C16	0.6199 (3)	0.3807 (2)	0.8303 (2)	0.0525 (7)
H16A	0.6973	0.3373	0.8140	0.063*
H16B	0.5466	0.3605	0.7867	0.063*
C17	0.5796 (2)	0.36350 (19)	0.94063 (18)	0.0343 (5)
C18	0.7903 (3)	0.4452 (2)	1.0088 (2)	0.0494 (7)
H18B	0.8291	0.5060	1.0412	0.074*
H18C	0.8329	0.4345	0.9454	0.074*
H18D	0.8033	0.3835	1.0498	0.074*
C19	0.4282 (3)	0.3522 (2)	0.9490 (2)	0.0419 (6)
H19A	0.3857	0.4195	0.9331	0.050*
H19B	0.3968	0.2996	0.9016	0.050*
H2	0.3200 (19)	0.288 (2)	1.041 (2)	0.065 (10)*
H3	0.595 (4)	0.242 (3)	1.023 (2)	0.098 (16)*

	U11	U22	U33	U12	U13	U23
O1	0.0825 (17)	0.0374 (11)	0.0847 (16)	0.0077 (11)	0.0139 (13)	−0.0098 (11)
O2	0.0399 (11)	0.0470 (11)	0.0606 (13)	−0.0140 (9)	0.0059 (9)	0.0023 (9)
O3	0.0407 (11)	0.0276 (9)	0.0702 (15)	0.0056 (8)	0.0070 (10)	0.0029 (9)
C1	0.0666 (19)	0.0341 (14)	0.0384 (14)	−0.0083 (13)	0.0058 (13)	−0.0056 (11)
C2	0.064 (2)	0.0374 (14)	0.0500 (17)	−0.0081 (14)	0.0078 (15)	−0.0113 (12)
C3	0.0394 (14)	0.0333 (14)	0.0627 (17)	−0.0052 (12)	0.0067 (13)	−0.0055 (12)
C4	0.0438 (15)	0.0303 (13)	0.0520 (15)	−0.0035 (11)	−0.0025 (13)	0.0058 (11)
C5	0.0342 (13)	0.0307 (12)	0.0418 (14)	−0.0074 (10)	0.0000 (11)	0.0038 (10)
C6	0.0580 (17)	0.0341 (14)	0.0395 (14)	−0.0086 (13)	0.0047 (12)	0.0086 (11)
C7	0.0672 (19)	0.0362 (14)	0.0300 (13)	−0.0089 (14)	−0.0019 (13)	0.0038 (10)
C8	0.0377 (12)	0.0302 (12)	0.0319 (12)	−0.0034 (10)	0.0021 (10)	0.0003 (9)
C9	0.0335 (12)	0.0270 (11)	0.0326 (12)	−0.0035 (10)	0.0008 (10)	0.0013 (9)
C10	0.0375 (13)	0.0287 (12)	0.0325 (13)	−0.0033 (10)	−0.0022 (10)	−0.0002 (9)
C11	0.0582 (17)	0.0310 (12)	0.0288 (12)	−0.0027 (12)	−0.0022 (12)	0.0035 (9)
C12	0.0461 (15)	0.0276 (12)	0.0291 (12)	−0.0033 (11)	0.0013 (10)	0.0052 (9)
C13	0.0276 (12)	0.0288 (11)	0.0354 (13)	−0.0004 (10)	0.0002 (10)	−0.0006 (9)
C14	0.0392 (13)	0.0312 (12)	0.0305 (12)	−0.0036 (11)	0.0015 (10)	−0.0007 (9)
C15	0.085 (2)	0.0407 (15)	0.0373 (15)	−0.0107 (16)	0.0157 (15)	−0.0060 (12)
C16	0.071 (2)	0.0397 (15)	0.0470 (16)	−0.0072 (15)	0.0116 (15)	−0.0112 (13)
C17	0.0348 (12)	0.0263 (12)	0.0417 (13)	0.0010 (10)	0.0006 (11)	−0.0003 (10)
C18	0.0350 (15)	0.0390 (15)	0.074 (2)	0.0006 (12)	−0.0044 (14)	−0.0035 (14)
C19	0.0380 (13)	0.0345 (14)	0.0532 (15)	−0.0042 (11)	−0.0071 (12)	0.0012 (12)

O1—C3	1.225 (3)	C9—C10	1.549 (3)
O2—C19	1.413 (3)	C9—H9	0.9800
O2—H2	0.84 (3)	C10—H10	0.9800
O3—C17	1.434 (3)	C11—C12	1.530 (3)
O3—H3	0.84 (3)	C11—H11A	0.9700
C1—C2	1.526 (4)	C11—H11B	0.9700
C1—C10	1.529 (3)	C12—C13	1.523 (3)
C1—H1A	0.9700	C12—H12A	0.9700
C1—H1B	0.9700	C12—H12B	0.9700
C2—C3	1.493 (4)	C13—C14	1.537 (3)
C2—H2A	0.9700	C13—C18	1.543 (3)
C2—H2B	0.9700	C13—C17	1.563 (3)
C3—C4	1.463 (4)	C14—C15	1.533 (3)
C4—C5	1.334 (4)	C14—H14	0.9800
C4—H4	0.9300	C15—C16	1.536 (4)
C5—C6	1.505 (4)	C15—H15A	0.9700
C5—C10	1.514 (3)	C15—H15B	0.9700
C6—C7	1.524 (3)	C16—C17	1.546 (4)
C6—H6A	0.9700	C16—H16A	0.9700
C6—H6B	0.9700	C16—H16B	0.9700
C7—C8	1.527 (3)	C17—C19	1.520 (3)
C7—H7A	0.9700	C18—H18B	0.9600
C7—H7B	0.9700	C18—H18C	0.9600
C8—C14	1.524 (3)	C18—H18D	0.9600
C8—C9	1.539 (3)	C19—H19A	0.9700
C8—H8	0.9800	C19—H19B	0.9700
C9—C11	1.537 (3)
C19—O2—H2	106 (2)	C12—C11—H11A	108.9
C17—O3—H3	110 (3)	C9—C11—H11A	108.9
C2—C1—C10	111.0 (2)	C12—C11—H11B	108.9
C2—C1—H1A	109.4	C9—C11—H11B	108.9
C10—C1—H1A	109.4	H11A—C11—H11B	107.8
C2—C1—H1B	109.4	C13—C12—C11	111.6 (2)
C10—C1—H1B	109.4	C13—C12—H12A	109.3
H1A—C1—H1B	108.0	C11—C12—H12A	109.3
C3—C2—C1	110.9 (2)	C13—C12—H12B	109.3
C3—C2—H2A	109.5	C11—C12—H12B	109.3
C1—C2—H2A	109.5	H12A—C12—H12B	108.0
C3—C2—H2B	109.5	C12—C13—C14	107.80 (19)
C1—C2—H2B	109.5	C12—C13—C18	109.8 (2)
H2A—C2—H2B	108.1	C14—C13—C18	112.4 (2)
O1—C3—C4	122.2 (3)	C12—C13—C17	117.6 (2)
O1—C3—C2	122.0 (3)	C14—C13—C17	101.23 (18)
C4—C3—C2	115.7 (2)	C18—C13—C17	107.9 (2)
C5—C4—C3	123.2 (3)	C8—C14—C15	118.7 (2)
C5—C4—H4	118.4	C8—C14—C13	113.9 (2)
C3—C4—H4	118.4	C15—C14—C13	103.9 (2)
C4—C5—C6	121.0 (2)	C8—C14—H14	106.5
C4—C5—C10	122.3 (2)	C15—C14—H14	106.5
C6—C5—C10	116.6 (2)	C13—C14—H14	106.5
C5—C6—C7	114.4 (2)	C14—C15—C16	103.9 (2)
C5—C6—H6A	108.7	C14—C15—H15A	111.0
C7—C6—H6A	108.7	C16—C15—H15A	111.0
C5—C6—H6B	108.7	C14—C15—H15B	111.0
C7—C6—H6B	108.7	C16—C15—H15B	111.0
H6A—C6—H6B	107.6	H15A—C15—H15B	109.0
C6—C7—C8	111.2 (2)	C15—C16—C17	108.1 (2)
C6—C7—H7A	109.4	C15—C16—H16A	110.1
C8—C7—H7A	109.4	C17—C16—H16A	110.1
C6—C7—H7B	109.4	C15—C16—H16B	110.1
C8—C7—H7B	109.4	C17—C16—H16B	110.1
H7A—C7—H7B	108.0	H16A—C16—H16B	108.4
C14—C8—C7	112.5 (2)	O3—C17—C19	107.4 (2)
C14—C8—C9	109.51 (19)	O3—C17—C16	108.3 (2)
C7—C8—C9	109.1 (2)	C19—C17—C16	110.0 (2)
C14—C8—H8	108.5	O3—C17—C13	113.66 (19)
C7—C8—H8	108.5	C19—C17—C13	114.7 (2)
C9—C8—H8	108.5	C16—C17—C13	102.65 (19)
C11—C9—C8	112.66 (19)	C13—C18—H18B	109.5
C11—C9—C10	111.39 (19)	C13—C18—H18C	109.5
C8—C9—C10	111.39 (19)	H18B—C18—H18C	109.5
C11—C9—H9	107.0	C13—C18—H18D	109.5
C8—C9—H9	107.0	H18B—C18—H18D	109.5
C10—C9—H9	107.0	H18C—C18—H18D	109.5
C5—C10—C1	111.2 (2)	O2—C19—C17	110.1 (2)
C5—C10—C9	111.69 (19)	O2—C19—H19A	109.6
C1—C10—C9	111.8 (2)	C17—C19—H19A	109.6
C5—C10—H10	107.3	O2—C19—H19B	109.6
C1—C10—H10	107.3	C17—C19—H19B	109.6
C9—C10—H10	107.3	H19A—C19—H19B	108.2
C12—C11—C9	113.1 (2)
C10—C1—C2—C3	58.7 (3)	C11—C12—C13—C18	65.7 (3)
C1—C2—C3—O1	145.9 (3)	C11—C12—C13—C17	−170.4 (2)
C1—C2—C3—C4	−37.6 (4)	C7—C8—C14—C15	59.1 (3)
O1—C3—C4—C5	−178.4 (3)	C9—C8—C14—C15	−179.4 (2)
C2—C3—C4—C5	5.1 (4)	C7—C8—C14—C13	−178.2 (2)
C3—C4—C5—C6	−169.7 (3)	C9—C8—C14—C13	−56.7 (3)
C3—C4—C5—C10	7.0 (4)	C12—C13—C14—C8	60.2 (3)
C4—C5—C6—C7	−140.6 (3)	C18—C13—C14—C8	−60.9 (3)
C10—C5—C6—C7	42.5 (3)	C17—C13—C14—C8	−175.7 (2)
C5—C6—C7—C8	−50.0 (3)	C12—C13—C14—C15	−169.2 (2)
C6—C7—C8—C14	−179.5 (2)	C18—C13—C14—C15	69.7 (3)
C6—C7—C8—C9	58.8 (3)	C17—C13—C14—C15	−45.2 (2)
C14—C8—C9—C11	50.0 (3)	C8—C14—C15—C16	161.0 (2)
C7—C8—C9—C11	173.5 (2)	C13—C14—C15—C16	33.4 (3)
C14—C8—C9—C10	175.97 (19)	C14—C15—C16—C17	−8.6 (3)
C7—C8—C9—C10	−60.5 (3)	C15—C16—C17—O3	−139.3 (3)
C4—C5—C10—C1	14.6 (4)	C15—C16—C17—C19	103.6 (3)
C6—C5—C10—C1	−168.6 (2)	C15—C16—C17—C13	−18.8 (3)
C4—C5—C10—C9	140.3 (2)	C12—C13—C17—O3	−87.4 (3)
C6—C5—C10—C9	−42.9 (3)	C14—C13—C17—O3	155.4 (2)
C2—C1—C10—C5	−46.5 (3)	C18—C13—C17—O3	37.3 (3)
C2—C1—C10—C9	−172.2 (2)	C12—C13—C17—C19	36.6 (3)
C11—C9—C10—C5	178.6 (2)	C14—C13—C17—C19	−80.5 (2)
C8—C9—C10—C5	51.9 (3)	C18—C13—C17—C19	161.3 (2)
C11—C9—C10—C1	−56.0 (3)	C12—C13—C17—C16	155.8 (2)
C8—C9—C10—C1	177.2 (2)	C14—C13—C17—C16	38.7 (2)
C8—C9—C11—C12	−50.1 (3)	C18—C13—C17—C16	−79.5 (3)
C10—C9—C11—C12	−176.1 (2)	O3—C17—C19—O2	53.7 (3)
C9—C11—C12—C13	54.1 (3)	C16—C17—C19—O2	171.4 (2)
C11—C12—C13—C14	−56.9 (3)	C13—C17—C19—O2	−73.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.84 (3)	1.95 (3)	2.779 (3)	171 (3)
O3—H3···O1ii	0.84 (3)	2.18 (3)	2.904 (3)	144 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.84 (3)	1.95 (3)	2.779 (3)	171 (3)
O3—H3⋯O1ii	0.84 (3)	2.18 (3)	2.904 (3)	144 (4)

Symmetry codes: (i) ; (ii) .