17-Oxo-13α-androst-5-en-3β-yl acetate

The title compound, C₂₁H₃₀O₃ was synthetized by the epimerization of 17-oxoandrost-5-en-3β-yl acetate. There are four fused rings. The A/B and B/C ring fusions are trans, whereas the C/D ring fusion is cis. Rings A and C adopt chair conformations, ring B a distorted half-chair conformation and ring D a 14β-envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 133 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.039
• wR factor = 0.101
• Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      24.69 Deg.

Author Response: The value is only slightly under the requirements of Acta E. Whereas the resolution is 0.85 A, the data set is still very strong at this resolution, about 10 sigma.

Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       1.00 mm

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 8 for a
            non-centrosymmetric structure, where ZMAX < 18
            sine(theta)/lambda                0.5877
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   7.0130
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5877
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      24.69 Deg.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.01
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.

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           24.69
           From the CIF: _reflns_number_total               1613
           Count of symmetry unique reflns         1668
           Completeness (_total/calc)             96.70%
           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 C3     = .          S
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    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

   7 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
   8 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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

17-Oxo-13α-androst-5-en-3β-yl acetate

Crystal data

C21H30O3	F(000) = 360
Mr = 330.45	Dx = 1.190 Mg m^−3
Monoclinic, P21	Melting point = 144–145 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 6.332 (2) Å	Cell parameters from 2917 reflections
b = 10.729 (2) Å	θ = 2.4–24.7°
c = 13.787 (2) Å	µ = 0.08 mm^−1
β = 100.04 (3)°	T = 133 K
V = 922.3 (4) Å^3	Prism, colourless
Z = 2	1.00 × 0.80 × 0.60 mm

Data collection

Stoe IPDS-II diffractometer	1613 independent reflections
Radiation source: fine-focus sealed tube	1459 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 24.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −7→7
Tmin = 0.927, Tmax = 0.955	k = −12→12
2917 measured reflections	l = 0→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0867P)^2] where P = (Fo^2 + 2Fc^2)/3
1613 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.21 e Å^−3
41 restraints	Δρmin = −0.15 e Å^−3

Special details

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	Occ. (<1)
O3	0.6611 (3)	0.5935 (2)	0.94324 (16)	0.0502 (6)
O1	−0.2038 (3)	−0.10723 (17)	0.63349 (13)	0.0374 (4)
C14	0.1568 (4)	0.5970 (2)	0.78362 (17)	0.0309 (5)
H14	0.0069	0.6291	0.7784	0.037*
C4	−0.0539 (4)	0.0996 (3)	0.61213 (18)	0.0342 (6)
H4A	0.0821	0.0576	0.6056	0.041*
H4B	−0.1393	0.1099	0.5453	0.041*
C11	0.2532 (4)	0.3733 (2)	0.91051 (17)	0.0331 (6)
H11A	0.4034	0.3626	0.9007	0.040*
H11B	0.2211	0.3065	0.9553	0.040*
C5	−0.0052 (4)	0.2261 (2)	0.65826 (17)	0.0307 (5)
C3	−0.1779 (4)	0.0184 (2)	0.6736 (2)	0.0351 (6)
H3	−0.3225	0.0559	0.6737	0.042*
C9	0.1025 (4)	0.3607 (2)	0.81112 (17)	0.0309 (5)
H9	−0.0465	0.3755	0.8235	0.037*
C2	−0.0595 (5)	0.0086 (3)	0.7783 (2)	0.0387 (6)
H2A	0.0793	−0.0342	0.7790	0.046*
H2B	−0.1449	−0.0416	0.8177	0.046*
C10	0.1059 (4)	0.2275 (2)	0.76606 (17)	0.0301 (5)
C8	0.1504 (4)	0.4630 (2)	0.74016 (17)	0.0307 (5)
H8	0.2942	0.4451	0.7227	0.037*
C13	0.2731 (4)	0.6076 (2)	0.89178 (18)	0.0329 (6)
C6	−0.0593 (4)	0.3295 (3)	0.60671 (18)	0.0349 (6)
H6	−0.1312	0.3205	0.5406	0.042*
C7	−0.0150 (4)	0.4590 (3)	0.64524 (19)	0.0378 (6)
H7A	−0.1506	0.4966	0.6577	0.045*
H7B	0.0375	0.5098	0.5944	0.045*
C1	−0.0196 (4)	0.1382 (3)	0.82403 (18)	0.0349 (6)
H1A	0.0614	0.1290	0.8919	0.042*
H1B	−0.1596	0.1766	0.8287	0.042*
C20	−0.3633 (5)	−0.1257 (3)	0.5573 (2)	0.0461 (7)
C12	0.2294 (4)	0.5001 (3)	0.95796 (19)	0.0358 (6)
H12A	0.0820	0.5081	0.9722	0.043*
H12B	0.3305	0.5052	1.0213	0.043*
C18	0.2177 (4)	0.7328 (3)	0.9372 (2)	0.0378 (6)
H18A	0.2667	0.8020	0.9004	0.057*
H18B	0.2891	0.7370	1.0061	0.057*
H18C	0.0621	0.7387	0.9338	0.057*
C15	0.2856 (4)	0.6854 (3)	0.7273 (2)	0.0399 (6)
H15A	0.2678	0.6620	0.6569	0.048*
H15B	0.2391	0.7729	0.7323	0.048*
C17	0.5082 (4)	0.6188 (3)	0.88010 (19)	0.0374 (6)
C21	−0.3705 (4)	−0.2573 (3)	0.5211 (2)	0.0405 (6)
H21A	−0.4502	−0.3088	0.5611	0.061*
H21B	−0.2241	−0.2894	0.5265	0.061*
H21C	−0.4420	−0.2600	0.4522	0.061*
O2	−0.517 (5)	−0.056 (5)	0.554 (7)	0.073 (12)	0.25 (9)
O2A	−0.472 (4)	−0.0427 (6)	0.514 (2)	0.074 (5)	0.75 (9)
C19	0.3378 (4)	0.1793 (3)	0.77203 (19)	0.0364 (6)
H19A	0.4008	0.1632	0.8410	0.055*
H19B	0.4234	0.2422	0.7448	0.055*
H19C	0.3361	0.1020	0.7341	0.055*
C16	0.5196 (4)	0.6679 (3)	0.7788 (2)	0.0465 (7)
H16A	0.5944	0.6079	0.7421	0.056*
H16B	0.5974	0.7483	0.7833	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0304 (9)	0.0583 (13)	0.0576 (12)	0.0013 (9)	−0.0042 (9)	−0.0067 (10)
O1	0.0368 (9)	0.0335 (9)	0.0403 (10)	0.0014 (8)	0.0024 (8)	−0.0032 (8)
C14	0.0246 (10)	0.0370 (13)	0.0306 (12)	0.0026 (10)	0.0036 (9)	0.0018 (10)
C4	0.0326 (12)	0.0396 (13)	0.0295 (12)	0.0021 (11)	0.0025 (10)	−0.0025 (11)
C11	0.0340 (12)	0.0348 (13)	0.0291 (12)	0.0011 (10)	0.0017 (10)	0.0035 (10)
C5	0.0246 (10)	0.0387 (13)	0.0293 (11)	0.0021 (10)	0.0056 (9)	−0.0003 (10)
C3	0.0328 (13)	0.0327 (13)	0.0400 (14)	0.0017 (10)	0.0070 (11)	−0.0017 (11)
C9	0.0254 (10)	0.0375 (13)	0.0299 (12)	0.0024 (10)	0.0051 (10)	0.0019 (10)
C2	0.0449 (15)	0.0349 (13)	0.0364 (13)	−0.0030 (11)	0.0078 (12)	0.0005 (11)
C10	0.0247 (11)	0.0355 (13)	0.0294 (11)	0.0026 (10)	0.0028 (9)	0.0003 (10)
C8	0.0277 (11)	0.0338 (13)	0.0300 (12)	0.0008 (10)	0.0038 (10)	−0.0004 (11)
C13	0.0264 (11)	0.0363 (13)	0.0351 (13)	−0.0003 (10)	0.0026 (10)	−0.0028 (11)
C6	0.0332 (12)	0.0432 (14)	0.0272 (11)	−0.0003 (11)	0.0022 (10)	0.0001 (11)
C7	0.0412 (14)	0.0390 (14)	0.0310 (12)	0.0042 (11)	0.0005 (11)	0.0018 (11)
C1	0.0357 (12)	0.0381 (14)	0.0313 (12)	−0.0003 (11)	0.0064 (10)	0.0012 (11)
C20	0.0403 (14)	0.0354 (15)	0.0580 (17)	−0.0019 (12)	−0.0044 (13)	−0.0025 (13)
C12	0.0333 (13)	0.0432 (14)	0.0295 (12)	−0.0020 (11)	0.0016 (11)	−0.0013 (11)
C18	0.0383 (13)	0.0370 (14)	0.0373 (13)	0.0011 (11)	0.0049 (11)	−0.0033 (11)
C15	0.0399 (14)	0.0377 (14)	0.0418 (14)	−0.0033 (11)	0.0058 (12)	−0.0003 (11)
C17	0.0301 (12)	0.0356 (14)	0.0447 (14)	−0.0008 (10)	0.0015 (11)	−0.0085 (11)
C21	0.0377 (13)	0.0386 (14)	0.0450 (14)	−0.0055 (11)	0.0066 (12)	−0.0021 (12)
O2	0.048 (8)	0.054 (10)	0.10 (3)	0.014 (7)	−0.021 (11)	−0.027 (14)
O2A	0.070 (5)	0.0367 (19)	0.095 (8)	0.003 (2)	−0.042 (5)	−0.007 (3)
C19	0.0282 (12)	0.0406 (14)	0.0386 (13)	0.0060 (10)	0.0011 (10)	−0.0022 (11)
C16	0.0340 (13)	0.0521 (17)	0.0550 (17)	−0.0101 (12)	0.0125 (13)	−0.0027 (14)

Geometric parameters (Å, º)

O3—C17	1.214 (3)	C13—C12	1.526 (4)
O1—C20	1.339 (3)	C13—C17	1.530 (3)
O1—C3	1.456 (3)	C13—C18	1.548 (4)
C14—C15	1.545 (4)	C6—C7	1.496 (4)
C14—C13	1.548 (3)	C6—H6	0.9500
C14—C8	1.556 (4)	C7—H7A	0.9900
C14—H14	1.0000	C7—H7B	0.9900
C4—C5	1.508 (4)	C1—H1A	0.9900
C4—C3	1.525 (4)	C1—H1B	0.9900
C4—H4A	0.9900	C20—O2	1.225 (14)
C4—H4B	0.9900	C20—O2A	1.218 (6)
C11—C9	1.533 (3)	C20—C21	1.496 (4)
C11—C12	1.529 (4)	C12—H12A	0.9900
C11—H11A	0.9900	C12—H12B	0.9900
C11—H11B	0.9900	C18—H18A	0.9800
C5—C6	1.329 (4)	C18—H18B	0.9800
C5—C10	1.529 (3)	C18—H18C	0.9800
C3—C2	1.509 (4)	C15—C16	1.539 (4)
C3—H3	1.0000	C15—H15A	0.9900
C9—C8	1.535 (3)	C15—H15B	0.9900
C9—C10	1.560 (3)	C17—C16	1.506 (4)
C9—H9	1.0000	C21—H21A	0.9800
C2—C1	1.530 (4)	C21—H21B	0.9800
C2—H2A	0.9900	C21—H21C	0.9800
C2—H2B	0.9900	C19—H19A	0.9800
C10—C19	1.545 (3)	C19—H19B	0.9800
C10—C1	1.553 (3)	C19—H19C	0.9800
C8—C7	1.528 (3)	C16—H16A	0.9900
C8—H8	1.0000	C16—H16B	0.9900
C20—O1—C3	117.06 (19)	C5—C6—H6	117.6
C15—C14—C13	103.60 (19)	C7—C6—H6	117.6
C15—C14—C8	110.7 (2)	C6—C7—C8	112.9 (2)
C13—C14—C8	114.5 (2)	C6—C7—H7A	109.0
C15—C14—H14	109.3	C8—C7—H7A	109.0
C13—C14—H14	109.3	C6—C7—H7B	109.0
C8—C14—H14	109.3	C8—C7—H7B	109.0
C5—C4—C3	111.5 (2)	H7A—C7—H7B	107.8
C5—C4—H4A	109.3	C2—C1—C10	114.3 (2)
C3—C4—H4A	109.3	C2—C1—H1A	108.7
C5—C4—H4B	109.3	C10—C1—H1A	108.7
C3—C4—H4B	109.3	C2—C1—H1B	108.7
H4A—C4—H4B	108.0	C10—C1—H1B	108.7
C9—C11—C12	111.6 (2)	H1A—C1—H1B	107.6
C9—C11—H11A	109.3	O2—C20—O1	115 (2)
C12—C11—H11A	109.3	O2A—C20—O1	124.3 (5)
C9—C11—H11B	109.3	O2—C20—C21	126.2 (14)
C12—C11—H11B	109.3	O2A—C20—C21	122.9 (7)
H11A—C11—H11B	108.0	O1—C20—C21	112.1 (2)
C6—C5—C4	120.7 (2)	C13—C12—C11	112.1 (2)
C6—C5—C10	122.9 (2)	C13—C12—H12A	109.2
C4—C5—C10	116.4 (2)	C11—C12—H12A	109.2
O1—C3—C2	107.6 (2)	C13—C12—H12B	109.2
O1—C3—C4	110.6 (2)	C11—C12—H12B	109.2
C2—C3—C4	110.7 (2)	H12A—C12—H12B	107.9
O1—C3—H3	109.3	C13—C18—H18A	109.5
C2—C3—H3	109.3	C13—C18—H18B	109.5
C4—C3—H3	109.3	H18A—C18—H18B	109.5
C11—C9—C8	110.22 (19)	C13—C18—H18C	109.5
C11—C9—C10	112.74 (19)	H18A—C18—H18C	109.5
C8—C9—C10	112.51 (19)	H18B—C18—H18C	109.5
C11—C9—H9	107.0	C16—C15—C14	104.1 (2)
C8—C9—H9	107.0	C16—C15—H15A	110.9
C10—C9—H9	107.0	C14—C15—H15A	110.9
C3—C2—C1	110.4 (2)	C16—C15—H15B	110.9
C3—C2—H2A	109.6	C14—C15—H15B	110.9
C1—C2—H2A	109.6	H15A—C15—H15B	109.0
C3—C2—H2B	109.6	O3—C17—C16	125.6 (2)
C1—C2—H2B	109.6	O3—C17—C13	125.2 (3)
H2A—C2—H2B	108.1	C16—C17—C13	109.2 (2)
C5—C10—C19	108.66 (19)	C20—C21—H21A	109.5
C5—C10—C1	107.72 (19)	C20—C21—H21B	109.5
C19—C10—C1	109.4 (2)	H21A—C21—H21B	109.5
C5—C10—C9	111.10 (19)	C20—C21—H21C	109.5
C19—C10—C9	111.4 (2)	H21A—C21—H21C	109.5
C1—C10—C9	108.5 (2)	H21B—C21—H21C	109.5
C7—C8—C9	110.1 (2)	C10—C19—H19A	109.5
C7—C8—C14	108.89 (19)	C10—C19—H19B	109.5
C9—C8—C14	114.2 (2)	H19A—C19—H19B	109.5
C7—C8—H8	107.8	C10—C19—H19C	109.5
C9—C8—H8	107.8	H19A—C19—H19C	109.5
C14—C8—H8	107.8	H19B—C19—H19C	109.5
C12—C13—C17	113.8 (2)	C17—C16—C15	105.9 (2)
C12—C13—C18	109.7 (2)	C17—C16—H16A	110.6
C17—C13—C18	105.5 (2)	C15—C16—H16A	110.6
C12—C13—C14	114.5 (2)	C17—C16—H16B	110.6
C17—C13—C14	102.27 (19)	C15—C16—H16B	110.6
C18—C13—C14	110.5 (2)	H16A—C16—H16B	108.7
C5—C6—C7	124.7 (2)
C3—C4—C5—C6	−126.6 (3)	C15—C14—C13—C17	−36.9 (2)
C3—C4—C5—C10	52.8 (3)	C8—C14—C13—C17	83.8 (2)
C20—O1—C3—C2	157.3 (2)	C15—C14—C13—C18	75.1 (2)
C20—O1—C3—C4	−81.6 (3)	C8—C14—C13—C18	−164.2 (2)
C5—C4—C3—O1	−174.08 (18)	C4—C5—C6—C7	−179.0 (3)
C5—C4—C3—C2	−54.9 (3)	C10—C5—C6—C7	1.6 (4)
C12—C11—C9—C8	59.3 (3)	C5—C6—C7—C8	15.4 (4)
C12—C11—C9—C10	−174.0 (2)	C9—C8—C7—C6	−44.6 (3)
O1—C3—C2—C1	178.0 (2)	C14—C8—C7—C6	−170.5 (2)
C4—C3—C2—C1	57.0 (3)	C3—C2—C1—C10	−57.0 (3)
C6—C5—C10—C19	−111.2 (3)	C5—C10—C1—C2	50.7 (3)
C4—C5—C10—C19	69.4 (3)	C19—C10—C1—C2	−67.3 (3)
C6—C5—C10—C1	130.3 (3)	C9—C10—C1—C2	171.06 (19)
C4—C5—C10—C1	−49.0 (3)	C3—O1—C20—O2	−28 (6)
C6—C5—C10—C9	11.7 (3)	C3—O1—C20—O2A	8 (2)
C4—C5—C10—C9	−167.7 (2)	C3—O1—C20—C21	178.7 (2)
C11—C9—C10—C5	−167.26 (19)	C17—C13—C12—C11	−69.5 (3)
C8—C9—C10—C5	−41.9 (3)	C18—C13—C12—C11	172.6 (2)
C11—C9—C10—C19	−46.0 (3)	C14—C13—C12—C11	47.7 (3)
C8—C9—C10—C19	79.4 (2)	C9—C11—C12—C13	−58.0 (3)
C11—C9—C10—C1	74.5 (2)	C13—C14—C15—C16	37.2 (3)
C8—C9—C10—C1	−160.09 (18)	C8—C14—C15—C16	−86.0 (2)
C11—C9—C8—C7	−174.0 (2)	C12—C13—C17—O3	−33.4 (4)
C10—C9—C8—C7	59.2 (3)	C18—C13—C17—O3	86.9 (3)
C11—C9—C8—C14	−51.1 (3)	C14—C13—C17—O3	−157.5 (3)
C10—C9—C8—C14	−177.89 (18)	C12—C13—C17—C16	147.6 (2)
C15—C14—C8—C7	−77.9 (2)	C18—C13—C17—C16	−92.1 (2)
C13—C14—C8—C7	165.4 (2)	C14—C13—C17—C16	23.5 (3)
C15—C14—C8—C9	158.56 (19)	O3—C17—C16—C15	−179.8 (3)
C13—C14—C8—C9	41.9 (3)	C13—C17—C16—C15	−0.7 (3)
C15—C14—C13—C12	−160.5 (2)	C14—C15—C16—C17	−22.5 (3)
C8—C14—C13—C12	−39.8 (3)