3,17-Dioxoandrosta-4,6-dien-11-yl acetate

The synthesis and crystal structure analysis via X-ray diffraction of the title compound, C₂₀H₂₄O₄, (I), are described. The title compound is an androstadione bearing a diene in the A and B rings [Krause & Thorand (1999). Inorg. Chim. Acta, 296, 1-11]. The diene conjugates with the carbonyl group. Intermolecular H...O contacts (2.53 and 2.64 Å; C-H...O angles 161 and 158°) indicate hydrogen bonds.

Computing details

Data collection: Nonius KappaCCD software; cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C20H24O4	Dx = 1.266 Mg m^−3
Mr = 328.39	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 10662 reflections
a = 9.7567 (3) Å	θ = 3.1–27.5°
b = 10.3440 (3) Å	µ = 0.09 mm^−1
c = 17.0684 (6) Å	T = 291 K
V = 1722.60 (9) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.12 mm
F(000) = 704

Data collection

Nonius KappaCCD diffractometer	1217 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
Detector resolution: 10 vertical, 18 horizontal pixels mm^-1	h = −12→12
Method: 208 frames via ω–rotation (Δω = 1°) at different κ values and two times 30 s per frame scans	k = −13→13
10662 measured reflections	l = −22→22
2205 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.035	Calculated w = 1/[σ^2(Fo^2) + (0.040P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.078	(Δ/σ)max = 0.001
S = 0.93	Δρmax = 0.10 e Å^−3
2205 reflections	Δρmin = −0.11 e Å^−3
220 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0064 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.4 (14)

Special details

Experimental. The data collection covered almost the whole sphere of reciprocal space. The crystal to detector distance was 2.8 cm. Crystal decay was monitored by repeating the initial frames at the end of data collection. Analysing the duplicate reflections there was no indication for any decay.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0499 (2)	−0.1526 (2)	−0.28079 (11)	0.0938 (6)
O2	0.25114 (13)	0.03781 (12)	0.05679 (8)	0.0530 (4)
O3	0.0222 (2)	0.0794 (2)	0.33335 (11)	0.1062 (7)
O4	0.30436 (16)	0.24636 (16)	0.03861 (11)	0.0809 (6)
C1	−0.0406 (2)	−0.1870 (2)	−0.15573 (15)	0.0626 (6)
H1	−0.0783	−0.2659	−0.1705	0.075*
C2	0.0377 (3)	−0.1165 (2)	−0.21280 (16)	0.0659 (7)
C3	0.0980 (2)	0.0097 (2)	−0.18597 (14)	0.0661 (7)
H3A	0.0337	0.0789	−0.1971	0.079*
H3B	0.1812	0.0267	−0.2153	0.079*
C4	0.1307 (2)	0.0097 (2)	−0.09894 (13)	0.0550 (6)
H4A	0.1641	0.0943	−0.0836	0.066*
H4B	0.2024	−0.0529	−0.0884	0.066*
C5	−0.0624 (2)	−0.1452 (2)	−0.08219 (14)	0.0526 (6)
C6	−0.1586 (2)	−0.2105 (2)	−0.03095 (16)	0.0690 (7)
H6	−0.1987	−0.2870	−0.0481	0.083*
C7	−0.1918 (2)	−0.1659 (2)	0.03931 (16)	0.0664 (7)
H7	−0.2606	−0.2074	0.0674	0.080*
C8	−0.1225 (2)	−0.0512 (2)	0.07488 (12)	0.0495 (5)
H8	−0.1756	0.0259	0.0611	0.059*
C9	0.02192 (19)	−0.03745 (18)	0.03805 (12)	0.0434 (5)
H9	0.0695	−0.1196	0.0469	0.052*
C10	0.00343 (19)	−0.02388 (18)	−0.05079 (12)	0.0468 (5)
H10	−0.0624	0.0464	−0.0590	0.056*
C11	0.10926 (19)	0.0682 (2)	0.07661 (12)	0.0479 (5)
H11	0.0843	0.1531	0.0556	0.057*
C12	0.1037 (2)	0.0705 (2)	0.16567 (12)	0.0536 (6)
H12A	0.1465	0.1492	0.1845	0.064*
H12B	0.1554	−0.0022	0.1861	0.064*
C13	−0.0416 (2)	0.0639 (2)	0.19599 (12)	0.0516 (5)
C14	−0.1107 (2)	−0.0569 (2)	0.16349 (12)	0.0516 (6)
H14	−0.0491	−0.1291	0.1752	0.062*
C15	−0.2374 (2)	−0.0756 (2)	0.21578 (14)	0.0710 (7)
H15A	−0.2688	−0.1645	0.2147	0.085*
H15B	−0.3118	−0.0192	0.1998	0.085*
C16	−0.1831 (3)	−0.0385 (3)	0.29727 (14)	0.0737 (7)
H16A	−0.2512	0.0110	0.3258	0.088*
H16B	−0.1609	−0.1153	0.3273	0.088*
C17	−0.0565 (3)	0.0416 (3)	0.28346 (16)	0.0683 (7)
C18	−0.1217 (3)	0.1900 (2)	0.17902 (14)	0.0654 (7)
H18A	−0.2132	0.1824	0.1992	0.098*
H18B	−0.1253	0.2043	0.1235	0.098*
H18C	−0.0763	0.2614	0.2038	0.098*
C19	0.3388 (2)	0.1352 (2)	0.04178 (13)	0.0564 (6)
C20	0.4796 (2)	0.0836 (3)	0.02874 (16)	0.0764 (8)
H20A	0.4824	0.0374	−0.0200	0.115*
H20B	0.5035	0.0262	0.0708	0.115*
H20C	0.5437	0.1540	0.0271	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1054 (15)	0.1174 (15)	0.0587 (13)	0.0056 (13)	−0.0018 (11)	−0.0204 (12)
O2	0.0382 (7)	0.0515 (8)	0.0695 (10)	−0.0067 (8)	0.0041 (7)	0.0025 (8)
O3	0.1049 (15)	0.157 (2)	0.0567 (12)	−0.0196 (15)	−0.0039 (12)	−0.0003 (13)
O4	0.0693 (11)	0.0572 (11)	0.1162 (16)	−0.0161 (9)	−0.0030 (11)	0.0193 (11)
C1	0.0621 (14)	0.0562 (14)	0.0695 (17)	0.0016 (12)	−0.0059 (14)	−0.0153 (14)
C2	0.0632 (16)	0.0779 (17)	0.0567 (18)	0.0220 (14)	−0.0069 (15)	−0.0073 (15)
C3	0.0649 (14)	0.0786 (18)	0.0549 (16)	0.0060 (14)	0.0054 (12)	0.0034 (12)
C4	0.0528 (13)	0.0560 (13)	0.0563 (15)	0.0011 (11)	0.0018 (11)	0.0000 (10)
C5	0.0441 (13)	0.0488 (12)	0.0648 (16)	0.0038 (11)	−0.0064 (12)	−0.0020 (12)
C6	0.0671 (16)	0.0586 (14)	0.081 (2)	−0.0195 (14)	−0.0009 (16)	−0.0100 (14)
C7	0.0533 (13)	0.0662 (16)	0.0799 (19)	−0.0216 (12)	0.0087 (14)	−0.0007 (15)
C8	0.0419 (11)	0.0459 (12)	0.0607 (15)	−0.0023 (11)	0.0023 (10)	0.0033 (11)
C9	0.0393 (10)	0.0369 (10)	0.0539 (13)	0.0014 (9)	−0.0002 (10)	0.0012 (10)
C10	0.0401 (11)	0.0449 (11)	0.0556 (14)	−0.0001 (10)	−0.0033 (10)	−0.0002 (11)
C11	0.0377 (11)	0.0471 (12)	0.0588 (15)	−0.0001 (11)	0.0022 (10)	0.0024 (11)
C12	0.0516 (13)	0.0542 (13)	0.0551 (15)	−0.0021 (12)	−0.0011 (11)	−0.0004 (12)
C13	0.0507 (12)	0.0525 (13)	0.0517 (14)	0.0001 (11)	0.0041 (11)	0.0010 (11)
C14	0.0466 (12)	0.0504 (13)	0.0577 (15)	0.0002 (11)	0.0077 (11)	0.0083 (12)
C15	0.0634 (15)	0.0712 (15)	0.0785 (19)	−0.0028 (14)	0.0195 (14)	0.0089 (14)
C16	0.0759 (16)	0.0771 (16)	0.0679 (18)	0.0111 (15)	0.0234 (14)	0.0096 (15)
C17	0.0724 (16)	0.0751 (16)	0.0573 (17)	0.0046 (15)	0.0036 (14)	0.0012 (15)
C18	0.0702 (15)	0.0536 (13)	0.0724 (17)	0.0095 (12)	0.0083 (13)	−0.0008 (12)
C19	0.0506 (13)	0.0657 (16)	0.0527 (15)	−0.0149 (13)	−0.0002 (12)	0.0069 (13)
C20	0.0461 (13)	0.1017 (19)	0.0815 (18)	−0.0121 (15)	0.0094 (12)	0.0049 (16)

Geometric parameters (Å, º)

O1—C2	1.225 (3)	C9—H9	0.9800
O2—C19	1.346 (2)	C10—H10	0.9800
O2—C11	1.459 (2)	C11—C12	1.521 (3)
O3—C17	1.211 (3)	C11—H11	0.9800
O4—C19	1.200 (3)	C12—C13	1.511 (3)
C1—C5	1.344 (3)	C12—H12A	0.9700
C1—C2	1.437 (3)	C12—H12B	0.9700
C1—H1	0.9300	C13—C17	1.518 (3)
C2—C3	1.504 (3)	C13—C18	1.548 (3)
C3—C4	1.519 (3)	C13—C14	1.524 (3)
C3—H3A	0.9700	C14—C15	1.537 (3)
C3—H3B	0.9700	C14—H14	0.9800
C4—C10	1.529 (3)	C15—C16	1.537 (3)
C4—H4A	0.9700	C15—H15A	0.9700
C4—H4B	0.9700	C15—H15B	0.9700
C5—C6	1.449 (3)	C16—C17	1.506 (4)
C5—C10	1.508 (3)	C16—H16A	0.9700
C6—C7	1.325 (3)	C16—H16B	0.9700
C6—H6	0.9300	C18—H18A	0.9600
C7—C8	1.494 (3)	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600
C8—C14	1.518 (3)	C19—C20	1.491 (3)
C8—C9	1.549 (3)	C20—H20A	0.9600
C8—H8	0.9800	C20—H20B	0.9600
C9—C10	1.534 (3)	C20—H20C	0.9600
C9—C11	1.534 (3)
C19—O2—C11	119.08 (16)	C12—C11—H11	110.1
C5—C1—C2	123.6 (2)	C9—C11—H11	110.1
C5—C1—H1	118.2	C11—C12—C13	112.01 (17)
C2—C1—H1	118.2	C11—C12—H12A	109.2
O1—C2—C1	122.7 (3)	C13—C12—H12A	109.2
O1—C2—C3	121.0 (2)	C11—C12—H12B	109.2
C1—C2—C3	116.2 (2)	C13—C12—H12B	109.2
C2—C3—C4	112.3 (2)	H12A—C12—H12B	107.9
C2—C3—H3A	109.1	C17—C13—C12	115.68 (19)
C4—C3—H3A	109.1	C17—C13—C18	105.30 (18)
C2—C3—H3B	109.1	C12—C13—C18	111.80 (19)
C4—C3—H3B	109.1	C17—C13—C14	101.03 (19)
H3A—C3—H3B	107.9	C12—C13—C14	109.15 (18)
C3—C4—C10	110.78 (18)	C18—C13—C14	113.53 (17)
C3—C4—H4A	109.5	C8—C14—C15	121.52 (19)
C10—C4—H4A	109.5	C8—C14—C13	111.39 (17)
C3—C4—H4B	109.5	C15—C14—C13	104.34 (18)
C10—C4—H4B	109.5	C8—C14—H14	106.2
H4A—C4—H4B	108.1	C15—C14—H14	106.2
C1—C5—C6	121.1 (2)	C13—C14—H14	106.2
C1—C5—C10	122.1 (2)	C14—C15—C16	102.52 (18)
C6—C5—C10	116.7 (2)	C14—C15—H15A	111.3
C7—C6—C5	122.8 (2)	C16—C15—H15A	111.3
C7—C6—H6	118.6	C14—C15—H15B	111.3
C5—C6—H6	118.6	C16—C15—H15B	111.3
C6—C7—C8	122.2 (2)	H15A—C15—H15B	109.2
C6—C7—H7	118.9	C17—C16—C15	106.16 (18)
C8—C7—H7	118.9	C17—C16—H16A	110.5
C14—C8—C7	114.11 (18)	C15—C16—H16A	110.5
C14—C8—C9	109.83 (17)	C17—C16—H16B	110.5
C7—C8—C9	108.64 (17)	C15—C16—H16B	110.5
C14—C8—H8	108.0	H16A—C16—H16B	108.7
C7—C8—H8	108.0	O3—C17—C13	125.6 (2)
C9—C8—H8	108.0	O3—C17—C16	126.0 (2)
C10—C9—C11	115.11 (16)	C13—C17—C16	108.4 (2)
C10—C9—C8	107.62 (15)	C13—C18—H18A	109.5
C11—C9—C8	113.37 (16)	C13—C18—H18B	109.5
C10—C9—H9	106.7	H18A—C18—H18B	109.5
C11—C9—H9	106.7	C13—C18—H18C	109.5
C8—C9—H9	106.7	H18A—C18—H18C	109.5
C9—C10—C5	108.98 (16)	H18B—C18—H18C	109.5
C9—C10—C4	117.18 (16)	O4—C19—O2	123.2 (2)
C5—C10—C4	110.12 (18)	O4—C19—C20	126.5 (2)
C9—C10—H10	106.7	O2—C19—C20	110.3 (2)
C5—C10—H10	106.7	C19—C20—H20A	109.5
C4—C10—H10	106.7	C19—C20—H20B	109.5
O2—C11—C12	105.59 (17)	H20A—C20—H20B	109.5
O2—C11—C9	105.92 (15)	C19—C20—H20C	109.5
C12—C11—C9	114.86 (17)	H20A—C20—H20C	109.5
O2—C11—H11	110.1	H20B—C20—H20C	109.5
C5—C1—C2—O1	−175.7 (2)	C10—C9—C11—C12	168.14 (17)
C5—C1—C2—C3	0.7 (3)	C8—C9—C11—C12	43.6 (2)
O1—C2—C3—C4	−153.6 (2)	O2—C11—C12—C13	−164.17 (16)
C1—C2—C3—C4	29.9 (3)	C9—C11—C12—C13	−47.9 (3)
C2—C3—C4—C10	−55.8 (2)	C11—C12—C13—C17	169.51 (19)
C2—C1—C5—C6	170.7 (2)	C11—C12—C13—C18	−70.0 (2)
C2—C1—C5—C10	−4.9 (3)	C11—C12—C13—C14	56.5 (2)
C1—C5—C6—C7	−173.9 (2)	C7—C8—C14—C15	−55.4 (3)
C10—C5—C6—C7	1.9 (3)	C9—C8—C14—C15	−177.68 (18)
C5—C6—C7—C8	−6.1 (4)	C7—C8—C14—C13	−178.95 (17)
C6—C7—C8—C14	−147.6 (2)	C9—C8—C14—C13	58.8 (2)
C6—C7—C8—C9	−24.7 (3)	C17—C13—C14—C8	174.10 (19)
C14—C8—C9—C10	−176.59 (16)	C12—C13—C14—C8	−63.6 (2)
C7—C8—C9—C10	58.0 (2)	C18—C13—C14—C8	61.9 (2)
C14—C8—C9—C11	−48.1 (2)	C17—C13—C14—C15	41.3 (2)
C7—C8—C9—C11	−173.56 (17)	C12—C13—C14—C15	163.63 (18)
C11—C9—C10—C5	170.16 (16)	C18—C13—C14—C15	−70.9 (2)
C8—C9—C10—C5	−62.36 (19)	C8—C14—C15—C16	−165.3 (2)
C11—C9—C10—C4	44.3 (2)	C13—C14—C15—C16	−38.5 (2)
C8—C9—C10—C4	171.80 (16)	C14—C15—C16—C17	20.1 (2)
C1—C5—C10—C9	−151.3 (2)	C12—C13—C17—O3	32.1 (4)
C6—C5—C10—C9	32.9 (2)	C18—C13—C17—O3	−91.9 (3)
C1—C5—C10—C4	−21.4 (3)	C14—C13—C17—O3	149.8 (3)
C6—C5—C10—C4	162.76 (18)	C12—C13—C17—C16	−146.3 (2)
C3—C4—C10—C9	175.74 (17)	C18—C13—C17—C16	89.7 (2)
C3—C4—C10—C5	50.5 (2)	C14—C13—C17—C16	−28.7 (2)
C19—O2—C11—C12	−94.8 (2)	C15—C16—C17—O3	−173.1 (3)
C19—O2—C11—C9	142.98 (17)	C15—C16—C17—C13	5.3 (3)
C10—C9—C11—O2	−75.75 (19)	C11—O2—C19—O4	−5.2 (3)
C8—C9—C11—O2	159.74 (16)	C11—O2—C19—C20	175.85 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2^i	0.93	2.64	3.526 (3)	158
C10—H10···O4^ii	0.98	2.53	3.472 (2)	161

Symmetry codes: (i) x−1/2, −y−1/2, −z; (ii) x−1/2, −y+1/2, −z.