20-Oxopregna-5,16-dien-3β-yl acetate

In the title compound, C₂₃H₃₂O₃, there are four fused rings, three six-membered and one five-membered. The two cyclohexane rings adopt chair conformations and the cyclo­hexene ring displays an envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.143
• Data-to-parameter ratio = 6.9

checkCIF/PLATON results

No syntax errors found



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                0.6491
            Proportion of unique data used    0.6001
            Ratio reflections to parameters   6.8723
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.87
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         C2
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C20

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           27.47
           From the CIF: _reflns_number_total               2691
           Count of symmetry unique reflns         2690
           Completeness (_total/calc)            100.04%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C23H32O3	F(000) = 776.00
Mr = 356.50	Dx = 1.147 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14681 reflections
a = 8.8184 (4) Å	θ = 1.1–27.5°
b = 12.5785 (5) Å	µ = 0.07 mm^−1
c = 18.6036 (2) Å	T = 296 K
V = 2063.6 (1) Å^3	Chunk, colorless
Z = 4	0.60 × 0.52 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1615 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.044
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→11
Tmin = 0.946, Tmax = 0.993	k = −16→16
18683 measured reflections	l = −24→24
2691 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[0.0038Fo^2 + σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.143	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.24 e Å^−3
1615 reflections	Δρmin = −0.18 e Å^−3
235 parameters

Special details

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.6517 (5)	0.2795 (3)	0.1448 (2)	0.123 (1)
O2	0.5272 (3)	0.4292 (2)	0.1692 (1)	0.0776 (8)
O3	0.5505 (5)	0.4888 (2)	0.7738 (1)	0.107 (1)
C1	0.5399 (7)	0.3776 (4)	0.0484 (2)	0.113 (2)
C2	0.5792 (6)	0.3559 (4)	0.1251 (2)	0.085 (1)
C3	0.5494 (4)	0.4140 (3)	0.2460 (1)	0.063 (1)
C4	0.4237 (4)	0.3443 (3)	0.2748 (2)	0.066 (1)
C5	0.4377 (3)	0.3315 (2)	0.3564 (1)	0.0507 (8)
C6	0.4525 (3)	0.4336 (2)	0.3999 (1)	0.0506 (8)
C7	0.5693 (4)	0.5076 (2)	0.3621 (2)	0.0577 (8)
C8	0.5477 (4)	0.5203 (3)	0.2816 (2)	0.066 (1)
C9	0.4365 (3)	0.2351 (2)	0.3854 (1)	0.0537 (8)
C10	0.4453 (4)	0.2132 (2)	0.4635 (1)	0.0504 (8)
C11	0.4239 (3)	0.3123 (2)	0.5097 (1)	0.0439 (7)
C12	0.5110 (3)	0.4063 (2)	0.4764 (1)	0.0459 (7)
C13	0.4795 (3)	0.2939 (2)	0.5849 (1)	0.0456 (7)
C14	0.4643 (3)	0.3904 (2)	0.6355 (2)	0.0501 (8)
C15	0.5680 (4)	0.4762 (2)	0.6049 (2)	0.0585 (9)
C16	0.5244 (4)	0.5027 (2)	0.5270 (2)	0.0608 (9)
C17	0.4180 (4)	0.2014 (2)	0.6294 (2)	0.0606 (9)
C18	0.4680 (4)	0.2342 (3)	0.7028 (2)	0.065 (1)
C19	0.4994 (4)	0.3368 (3)	0.7069 (2)	0.0570 (9)
C20	0.5374 (4)	0.3936 (3)	0.7735 (2)	0.069 (1)
C21	0.5610 (6)	0.3314 (4)	0.8418 (2)	0.099 (2)
C22	0.2972 (4)	0.4895 (3)	0.4019 (2)	0.070 (1)
C23	0.3016 (4)	0.4318 (3)	0.6416 (2)	0.073 (1)
H1	0.6175	0.4234	0.0282	0.136*
H2	0.4427	0.4136	0.0467	0.136*
H3	0.5344	0.3123	0.0209	0.136*
H4	0.6460	0.3793	0.2545	0.075*
H5	0.3286	0.3794	0.2636	0.079*
H6	0.4262	0.2751	0.2519	0.079*
H7	0.5634	0.5769	0.3848	0.069*
H8	0.6693	0.4776	0.3699	0.069*
H9	0.6271	0.5650	0.2619	0.079*
H10	0.4498	0.5528	0.2727	0.079*
H11	0.4286	0.1750	0.3529	0.065*
H12	0.3689	0.1610	0.4762	0.061*
H13	0.5452	0.1849	0.4741	0.060*
H14	0.3170	0.3300	0.5112	0.053*
H15	0.6140	0.3808	0.4704	0.055*
H16	0.5876	0.2813	0.5802	0.054*
H17	0.5609	0.5392	0.6348	0.070*
H18	0.6715	0.4500	0.6054	0.070*
H19	0.5979	0.5519	0.5071	0.073*
H20	0.4254	0.5362	0.5283	0.073*
H21	0.3085	0.1971	0.6258	0.073*
H22	0.4623	0.1343	0.6146	0.073*
H23	0.4763	0.1857	0.7432	0.078*
H24	0.6671	0.3114	0.8445	0.119*
H25	0.4987	0.2678	0.8411	0.119*
H26	0.5347	0.3742	0.8834	0.119*
H27	0.2851	0.5359	0.3607	0.085*
H28	0.2886	0.5309	0.4457	0.085*
H29	0.2190	0.4353	0.4012	0.085*
H30	0.2830	0.4840	0.6043	0.087*
H31	0.2868	0.4643	0.6884	0.087*
H32	0.2317	0.3728	0.6360	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.183 (3)	0.097 (2)	0.089 (2)	0.042 (2)	0.002 (2)	−0.016 (2)
O2	0.095 (2)	0.090 (2)	0.047 (1)	0.016 (1)	−0.001 (1)	0.011 (1)
O3	0.178 (3)	0.069 (2)	0.073 (2)	−0.015 (2)	−0.010 (2)	−0.023 (1)
C1	0.152 (5)	0.131 (4)	0.056 (3)	0.004 (4)	0.010 (3)	0.002 (2)
C2	0.108 (3)	0.084 (3)	0.063 (2)	0.004 (2)	0.004 (2)	0.004 (2)
C3	0.071 (2)	0.071 (2)	0.045 (2)	0.008 (2)	−0.006 (2)	0.010 (1)
C4	0.077 (2)	0.068 (2)	0.053 (2)	−0.001 (2)	−0.012 (2)	0.001 (2)
C5	0.049 (2)	0.059 (2)	0.044 (2)	−0.003 (1)	−0.004 (1)	0.001 (1)
C6	0.051 (2)	0.049 (1)	0.052 (2)	0.006 (1)	−0.004 (1)	0.006 (1)
C7	0.065 (2)	0.051 (2)	0.058 (2)	0.003 (2)	−0.007 (2)	0.007 (1)
C8	0.076 (2)	0.062 (2)	0.059 (2)	0.007 (2)	−0.003 (2)	0.017 (2)
C9	0.058 (2)	0.054 (2)	0.049 (2)	−0.006 (1)	−0.003 (1)	−0.009 (1)
C10	0.054 (2)	0.045 (1)	0.052 (2)	−0.006 (1)	0.002 (1)	−0.001 (1)
C11	0.039 (1)	0.045 (1)	0.048 (2)	0.001 (1)	0.004 (1)	−0.003 (1)
C12	0.044 (1)	0.044 (1)	0.050 (2)	−0.000 (1)	0.000 (1)	−0.000 (1)
C13	0.045 (1)	0.044 (1)	0.048 (2)	−0.000 (1)	0.002 (1)	−0.006 (1)
C14	0.052 (2)	0.049 (1)	0.049 (2)	−0.002 (1)	0.003 (1)	−0.008 (1)
C15	0.071 (2)	0.048 (2)	0.056 (2)	−0.005 (1)	−0.002 (2)	−0.011 (1)
C16	0.076 (2)	0.045 (2)	0.060 (2)	−0.006 (2)	−0.003 (2)	−0.002 (1)
C17	0.077 (2)	0.053 (2)	0.051 (2)	−0.009 (2)	0.001 (1)	0.001 (1)
C18	0.092 (2)	0.062 (2)	0.041 (2)	−0.010 (2)	0.003 (2)	0.003 (1)
C19	0.058 (2)	0.062 (2)	0.050 (2)	−0.007 (2)	0.008 (1)	−0.009 (1)
C20	0.074 (2)	0.081 (2)	0.051 (2)	−0.011 (2)	0.000 (2)	−0.014 (2)
C21	0.130 (4)	0.118 (3)	0.049 (2)	−0.033 (3)	−0.008 (2)	−0.007 (2)
C22	0.062 (2)	0.077 (2)	0.071 (2)	0.015 (2)	−0.003 (2)	0.006 (2)
C23	0.069 (2)	0.078 (2)	0.070 (2)	0.015 (2)	0.011 (2)	−0.012 (2)

Geometric parameters (Å, º)

O1—C2	1.211 (6)	C1—H3	0.9700
O2—C2	1.317 (5)	C3—H4	0.9700
O2—C3	1.454 (4)	C4—H5	0.9700
O3—C20	1.204 (5)	C4—H6	0.9700
C1—C2	1.492 (6)	C7—H7	0.9700
C3—C4	1.512 (5)	C7—H8	0.9700
C3—C8	1.493 (5)	C8—H9	0.9700
C4—C5	1.530 (4)	C8—H10	0.9700
C5—C6	1.525 (4)	C9—H11	0.9700
C5—C9	1.328 (4)	C10—H12	0.9700
C6—C7	1.557 (4)	C10—H13	0.9700
C6—C12	1.551 (4)	C11—H14	0.9700
C6—C22	1.539 (4)	C12—H15	0.9700
C7—C8	1.517 (4)	C13—H16	0.9700
C9—C10	1.481 (4)	C15—H17	0.9700
C10—C11	1.526 (4)	C15—H18	0.9701
C11—C12	1.540 (4)	C16—H19	0.9700
C11—C13	1.500 (4)	C16—H20	0.9700
C12—C16	1.541 (4)	C17—H21	0.9700
C13—C14	1.542 (4)	C17—H22	0.9700
C13—C17	1.528 (4)	C18—H23	0.9700
C14—C15	1.526 (4)	C21—H24	0.9700
C14—C19	1.521 (4)	C21—H25	0.9700
C14—C23	1.530 (5)	C21—H26	0.9700
C15—C16	1.535 (4)	C22—H27	0.9700
C17—C18	1.494 (4)	C22—H28	0.9700
C18—C19	1.322 (5)	C22—H29	0.9700
C19—C20	1.469 (5)	C23—H30	0.9700
C20—C21	1.506 (5)	C23—H31	0.9700
C1—H1	0.9700	C23—H32	0.9700
C1—H2	0.9700
O1—C2—O2	123.4 (4)	H6—C4—H5	109.4581
O1—C2—C1	123.8 (4)	C5—C9—H11	117.2772
O2—C2—C1	112.7 (4)	C6—C7—H7	107.7260
C3—O2—C2	118.3 (3)	C6—C7—H8	107.5649
O2—C3—C4	109.0 (3)	C6—C12—H15	106.2268
O2—C3—C8	108.5 (3)	C6—C22—H27	110.7042
O3—C20—C19	120.6 (3)	C6—C22—H29	108.1291
O3—C20—C21	120.0 (3)	C6—C22—H28	109.5705
C8—C3—C4	110.7 (3)	C7—C8—H9	110.0974
C3—C4—C5	110.7 (3)	C7—C8—H10	109.0440
C3—C8—C7	110.1 (3)	H7—C7—C8	109.1512
C4—C5—C6	116.4 (3)	H8—C7—C8	107.6298
C4—C5—C9	119.9 (3)	H8—C7—H7	109.4608
C5—C6—C7	108.6 (2)	H10—C8—H9	109.4567
C9—C5—C6	123.7 (3)	H11—C9—C10	118.0866
C5—C6—C22	108.8 (2)	C9—C10—H12	109.1496
C5—C6—C12	109.2 (2)	C9—C10—H13	108.3725
C5—C9—C10	124.6 (3)	H12—C10—C11	109.2479
C6—C7—C8	115.2 (3)	H13—C10—C11	107.3140
C22—C6—C7	109.1 (2)	C10—C11—H14	108.9563
C12—C6—C7	109.1 (2)	H13—C10—H12	109.4580
C22—C6—C12	112.0 (2)	H14—C11—C12	108.6269
C6—C12—C11	112.0 (2)	C11—C12—H15	105.0391
C6—C12—C16	114.3 (2)	H14—C11—C13	109.0421
C9—C10—C11	113.2 (2)	C11—C13—H16	105.1687
C10—C11—C12	109.8 (2)	H15—C12—C16	104.9594
C10—C11—C13	111.1 (2)	C12—C16—H19	108.6403
C11—C12—C16	113.3 (2)	C12—C16—H20	106.6685
C13—C11—C12	109.3 (2)	H16—C13—C14	105.6000
C11—C13—C14	114.8 (2)	H16—C13—C17	105.8782
C11—C13—C17	120.4 (2)	C13—C17—H21	110.9611
C12—C16—C15	115.2 (2)	C13—C17—H22	111.4779
C13—C14—C15	106.1 (2)	C14—C15—H17	108.9930
C13—C14—C19	99.6 (2)	C14—C15—H18	108.6432
C13—C14—C23	113.2 (2)	C14—C23—H31	109.6021
C17—C13—C14	103.7 (2)	C14—C23—H30	109.6832
C13—C17—C18	100.4 (2)	C14—C23—H32	109.1232
C19—C14—C15	121.2 (3)	H17—C15—C16	110.3561
C23—C14—C15	110.4 (2)	H18—C15—C16	108.5281
C14—C15—C16	110.8 (3)	C15—C16—H19	109.4308
C14—C19—C18	109.8 (3)	C15—C16—H20	107.2723
C14—C19—C20	124.6 (3)	H18—C15—H17	109.4513
C23—C14—C19	106.1 (3)	H20—C16—H19	109.4551
C17—C18—C19	112.7 (3)	H21—C17—C18	111.8782
C18—C19—C20	124.8 (3)	H22—C17—C18	112.4700
C19—C20—C21	119.4 (3)	C17—C18—H23	123.7834
O2—C3—H4	109.7674	H22—C17—H21	109.4649
H1—C1—C2	108.4030	H23—C18—C19	123.5630
H2—C1—C2	108.8086	C20—C21—H24	108.0735
H3—C1—C2	111.1879	C20—C21—H25	109.7601
H2—C1—H1	109.4700	C20—C21—H26	110.5633
H3—C1—H1	109.4715	H25—C21—H24	109.4713
H3—C1—H2	109.4725	H26—C21—H24	109.4739
H4—C3—C4	108.9469	H26—C21—H25	109.4751
C3—C4—H6	110.2664	H29—C22—H27	109.4669
C3—C4—H5	107.0486	H28—C22—H27	109.4700
H4—C3—C8	109.8698	H29—C22—H28	109.4764
C3—C8—H9	110.0548	H31—C23—H30	109.4705
C3—C8—H10	108.0981	H32—C23—H30	109.4710
H6—C4—C5	109.8976	H32—C23—H31	109.4768
H5—C4—C5	109.4012
C3—O2—C2—O1	−4.1 (6)	C13—C11—C12—C6	−176.8 (2)
C3—O2—C2—C1	176.2 (4)	C13—C11—C12—C16	−45.6 (3)
C2—O2—C3—C4	−84.3 (3)	C10—C11—C13—C14	179.3 (2)
C2—O2—C3—C8	155.1 (3)	C10—C11—C13—C17	−55.5 (3)
O2—C3—C4—C5	−176.8 (3)	C12—C11—C13—C14	58.0 (3)
C8—C3—C4—C5	−57.5 (4)	C12—C11—C13—C17	−176.8 (2)
O2—C3—C8—C7	179.5 (3)	C6—C12—C16—C15	174.6 (3)
C4—C3—C8—C7	59.9 (4)	C11—C12—C16—C15	44.7 (4)
C3—C4—C5—C6	51.7 (4)	C11—C13—C14—C15	−64.3 (3)
C3—C4—C5—C9	−128.4 (3)	C11—C13—C14—C19	169.1 (2)
C4—C5—C6—C7	−45.0 (3)	C11—C13—C14—C23	56.9 (3)
C4—C5—C6—C12	−163.9 (2)	C17—C13—C14—C15	162.2 (2)
C4—C5—C6—C22	73.6 (3)	C17—C13—C14—C19	35.7 (3)
C9—C5—C6—C7	135.0 (3)	C17—C13—C14—C23	−76.6 (3)
C9—C5—C6—C12	16.2 (4)	C11—C13—C17—C18	−164.0 (3)
C9—C5—C6—C22	−106.4 (3)	C14—C13—C17—C18	−33.8 (3)
C4—C5—C9—C10	−178.4 (3)	C13—C14—C15—C16	57.5 (3)
C6—C5—C9—C10	1.6 (5)	C19—C14—C15—C16	169.7 (3)
C5—C6—C7—C8	47.2 (3)	C23—C14—C15—C16	−65.5 (3)
C12—C6—C7—C8	166.1 (3)	C13—C14—C19—C18	−24.8 (3)
C22—C6—C7—C8	−71.2 (3)	C13—C14—C19—C20	164.8 (3)
C5—C6—C12—C11	−46.9 (3)	C15—C14—C19—C18	−140.3 (3)
C5—C6—C12—C16	−177.6 (2)	C15—C14—C19—C20	49.3 (4)
C7—C6—C12—C11	−165.5 (2)	C23—C14—C19—C18	92.9 (3)
C7—C6—C12—C16	63.9 (3)	C23—C14—C19—C20	−77.5 (4)
C22—C6—C12—C11	73.6 (3)	C14—C15—C16—C12	−51.5 (4)
C22—C6—C12—C16	−57.0 (3)	C13—C17—C18—C19	19.5 (4)
C6—C7—C8—C3	−56.2 (4)	C17—C18—C19—C14	3.7 (4)
C5—C9—C10—C11	11.7 (4)	C17—C18—C19—C20	174.0 (3)
C9—C10—C11—C12	−41.7 (3)	C14—C19—C20—O3	−3.9 (6)
C9—C10—C11—C13	−162.8 (2)	C14—C19—C20—C21	176.4 (3)
C10—C11—C12—C6	61.2 (3)	C18—C19—C20—O3	−172.9 (4)
C10—C11—C12—C16	−167.7 (2)	C18—C19—C20—C21	7.5 (6)