3β-Acet­oxy-17,17-ethyl­enedi­oxy-15β,16β-methyl­ene-5-androsten-7β-ol

Zhou, W.; Zhong, G.-X.; Hu, W.-X.; Xia, C.-N.

doi:10.1107/S1600536806028534

3β-Acetoxy-17,17-ethylenedioxy-15β,16β-methylene-5-androsten-7β-ol

W. Zhou, G.-X. Zhong, W.-X. Hu and C.-N. Xia

In the title compound, C₂₄H₃₄O₅, the cyclohexane rings adopt chair conformations while the cyclohexene ring is in a half-chair conformation. Both five-membered rings adopt envelope conformations.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028534/ci2100sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028534/ci2100Isup2.hkl Contains datablock I

CCDC reference: 618165

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.044
wR factor = 0.120
Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C23
PLAT420_ALERT_2_B D-H Without Acceptor       O3     -   H3     ...          ?

Alert level C
PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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           25.18
           From the CIF: _reflns_number_total               2165
           Count of symmetry unique reflns         2163
           Completeness (_total/calc)            100.09%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         2
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R
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    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          S

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

  12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4, PSI and EAC in CAD-4 EXPRESS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.05; Farrugia, 1997)'; software used to prepare material for publication: SHELXL97.

3β-Acetoxy-17,17-ethylenedioxy-15β,16β-methylene-5-androsten-7β-ol top

Crystal data top

C₂₄H₃₄O₅	F(000) = 872
M_r = 402.51	D_x = 1.269 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 10.049 (3) Å	θ = 10.1–12.4°
b = 11.550 (3) Å	µ = 0.09 mm⁻¹
c = 18.149 (7) Å	T = 293 K
V = 2106.5 (11) Å³	Prism, colourless
Z = 4	0.50 × 0.40 × 0.35 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.016
Radiation source: fine-focus sealed tube	θ_max = 25.2°, θ_min = 2.1°
Graphite monochromator	h = 0→12
ω/2θ scans	k = 0→13
2307 measured reflections	l = −1→21
2165 independent reflections	3 standard reflections every 60 min
1415 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0425P)² + 0.9275P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
2165 reflections	Δρ_max = 0.28 e Å⁻³
267 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0097 (11)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1826 (3)	0.8400 (3)	1.16673 (15)	0.0536 (9)
O2	0.1020 (4)	0.6696 (3)	1.20524 (18)	0.0674 (10)
O3	0.3316 (5)	0.5116 (3)	0.84835 (19)	0.0739 (12)
H3	0.334 (7)	0.487 (5)	0.8059 (16)	0.12 (3)*
O4	0.1531 (3)	0.7986 (3)	0.55417 (15)	0.0537 (8)
O5	−0.0167 (3)	0.7075 (3)	0.61390 (15)	0.0553 (9)
C1	0.0961 (4)	0.9030 (4)	0.9701 (2)	0.0473 (11)
H1A	0.0854	0.9766	0.9450	0.057*
H1B	0.0116	0.8626	0.9675	0.057*
C2	0.1290 (5)	0.9263 (4)	1.0509 (2)	0.0497 (11)
H2A	0.2098	0.9718	1.0544	0.060*
H2B	0.0573	0.9697	1.0736	0.060*
C3	0.1472 (5)	0.8137 (4)	1.0902 (2)	0.0454 (11)
H3A	0.0638	0.7698	1.0890	0.055*
C4	0.2568 (5)	0.7430 (4)	1.0557 (2)	0.0480 (11)
H4A	0.2626	0.6686	1.0803	0.058*
H4B	0.3411	0.7826	1.0623	0.058*
C5	0.2320 (4)	0.7241 (4)	0.9739 (2)	0.0405 (10)
C6	0.2394 (4)	0.6192 (4)	0.9448 (2)	0.0464 (11)
H6	0.2541	0.5580	0.9770	0.056*
C7	0.2264 (5)	0.5901 (3)	0.8650 (2)	0.0445 (11)
H7	0.1415	0.5499	0.8577	0.053*
C8	0.2275 (4)	0.6975 (3)	0.8165 (2)	0.0349 (9)
H8	0.3195	0.7242	0.8107	0.042*
C9	0.1447 (4)	0.7948 (3)	0.8526 (2)	0.0381 (10)
H9	0.0570	0.7610	0.8626	0.046*
C10	0.2016 (4)	0.8313 (3)	0.9291 (2)	0.0353 (9)
C11	0.1193 (5)	0.8983 (4)	0.8021 (2)	0.0508 (12)
H11A	0.2013	0.9420	0.7973	0.061*
H11B	0.0541	0.9484	0.8253	0.061*
C12	0.0695 (5)	0.8664 (4)	0.7247 (2)	0.0530 (12)
H12A	−0.0178	0.8309	0.7280	0.064*
H12B	0.0621	0.9357	0.6947	0.064*
C13	0.1677 (4)	0.7820 (3)	0.6893 (2)	0.0399 (10)
C14	0.1686 (4)	0.6741 (3)	0.7402 (2)	0.0377 (10)
H14	0.0744	0.6581	0.7496	0.045*
C15	0.2147 (4)	0.5738 (4)	0.6929 (2)	0.0430 (11)
H15	0.1911	0.4951	0.7083	0.052*
C16	0.1869 (4)	0.6089 (4)	0.6141 (2)	0.0465 (11)
H16	0.1472	0.5508	0.5814	0.056*
C17	0.1249 (4)	0.7267 (4)	0.6154 (2)	0.0435 (10)
C18	0.3030 (5)	0.8447 (4)	0.6791 (3)	0.0542 (13)
H18A	0.3406	0.8239	0.6323	0.081*
H18B	0.3627	0.8220	0.7178	0.081*
H18C	0.2894	0.9269	0.6809	0.081*
C19	0.3289 (4)	0.9040 (4)	0.9207 (2)	0.0486 (11)
H19A	0.3763	0.9050	0.9666	0.073*
H19B	0.3056	0.9818	0.9071	0.073*
H19C	0.3842	0.8708	0.8831	0.073*
C20	0.1523 (5)	0.7619 (4)	1.2181 (2)	0.0489 (11)
C21	0.1881 (5)	0.8031 (5)	1.2935 (2)	0.0659 (14)
H21A	0.1675	0.7438	1.3288	0.099*
H21B	0.1383	0.8717	1.3048	0.099*
H21C	0.2815	0.8201	1.2954	0.099*
C22	0.3268 (5)	0.5888 (4)	0.6398 (2)	0.0535 (12)
H22A	0.3718	0.5196	0.6225	0.064*
H22B	0.3838	0.6559	0.6458	0.064*
C23	0.0453 (6)	0.7955 (7)	0.5068 (3)	0.106 (3)
H23A	0.0579	0.7368	0.4692	0.127*
H23B	0.0332	0.8699	0.4829	0.127*
C24	−0.0703 (5)	0.7675 (5)	0.5534 (3)	0.0755 (16)
H24A	−0.1152	0.8374	0.5694	0.091*
H24B	−0.1332	0.7193	0.5268	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.070 (2)	0.0599 (18)	0.0312 (16)	−0.0141 (18)	0.0041 (16)	−0.0075 (15)
O2	0.090 (3)	0.062 (2)	0.050 (2)	−0.016 (2)	0.0048 (19)	−0.0033 (19)
O3	0.118 (3)	0.055 (2)	0.049 (2)	0.037 (2)	−0.017 (2)	−0.0133 (17)
O4	0.0585 (19)	0.074 (2)	0.0285 (15)	−0.0093 (17)	−0.0023 (15)	0.0107 (16)
O5	0.0428 (17)	0.086 (2)	0.0369 (16)	−0.0057 (16)	−0.0074 (15)	−0.0011 (18)
C1	0.054 (3)	0.053 (3)	0.034 (2)	0.006 (2)	−0.007 (2)	−0.007 (2)
C2	0.054 (3)	0.057 (3)	0.038 (2)	0.010 (2)	0.000 (2)	−0.013 (2)
C3	0.054 (3)	0.055 (3)	0.027 (2)	−0.009 (2)	0.000 (2)	−0.013 (2)
C4	0.059 (3)	0.047 (2)	0.038 (2)	0.002 (2)	−0.006 (2)	−0.001 (2)
C5	0.046 (2)	0.045 (2)	0.030 (2)	0.000 (2)	−0.003 (2)	−0.001 (2)
C6	0.060 (3)	0.042 (2)	0.037 (2)	0.000 (2)	−0.008 (2)	0.005 (2)
C7	0.059 (3)	0.036 (2)	0.038 (2)	−0.003 (2)	−0.006 (2)	−0.006 (2)
C8	0.037 (2)	0.038 (2)	0.030 (2)	−0.0016 (19)	−0.0043 (18)	−0.0024 (19)
C9	0.038 (2)	0.043 (2)	0.033 (2)	−0.002 (2)	−0.0017 (18)	−0.0027 (19)
C10	0.038 (2)	0.040 (2)	0.028 (2)	0.0004 (19)	−0.0008 (18)	−0.0049 (19)
C11	0.066 (3)	0.047 (3)	0.039 (2)	0.019 (2)	−0.012 (2)	−0.007 (2)
C12	0.066 (3)	0.053 (3)	0.040 (2)	0.016 (2)	−0.011 (2)	−0.002 (2)
C13	0.043 (2)	0.042 (2)	0.035 (2)	0.000 (2)	−0.006 (2)	0.002 (2)
C14	0.036 (2)	0.043 (2)	0.034 (2)	−0.005 (2)	0.0004 (19)	−0.001 (2)
C15	0.048 (2)	0.043 (2)	0.038 (2)	−0.002 (2)	−0.001 (2)	−0.003 (2)
C16	0.050 (3)	0.055 (3)	0.034 (2)	−0.004 (2)	0.001 (2)	−0.007 (2)
C17	0.039 (2)	0.059 (3)	0.032 (2)	−0.009 (2)	−0.002 (2)	−0.001 (2)
C18	0.063 (3)	0.052 (3)	0.048 (3)	−0.013 (2)	−0.013 (3)	0.008 (2)
C19	0.055 (3)	0.049 (2)	0.041 (2)	−0.004 (2)	−0.004 (2)	−0.001 (2)
C20	0.049 (3)	0.057 (3)	0.041 (3)	0.003 (2)	0.006 (2)	−0.005 (2)
C21	0.082 (4)	0.083 (3)	0.033 (2)	−0.005 (3)	0.001 (3)	−0.008 (3)
C22	0.052 (3)	0.056 (3)	0.053 (3)	0.004 (2)	0.002 (2)	−0.006 (2)
C23	0.087 (4)	0.171 (7)	0.061 (3)	−0.025 (5)	−0.030 (4)	0.045 (5)
C24	0.062 (3)	0.104 (4)	0.061 (3)	0.000 (3)	−0.017 (3)	0.019 (3)

Geometric parameters (Å, º) top

O1—C20	1.332 (5)	C11—C12	1.536 (6)
O1—C3	1.466 (5)	C11—H11A	0.97
O2—C20	1.203 (5)	C11—H11B	0.97
O3—C7	1.426 (6)	C12—C13	1.529 (6)
O3—H3	0.82 (2)	C12—H12A	0.97
O4—C23	1.384 (6)	C12—H12B	0.97
O4—C17	1.417 (5)	C13—C17	1.546 (6)
O5—C24	1.406 (5)	C13—C18	1.551 (6)
O5—C17	1.441 (5)	C13—C14	1.551 (5)
C1—C2	1.527 (5)	C14—C15	1.515 (5)
C1—C10	1.538 (5)	C14—H14	0.98
C1—H1A	0.97	C15—C22	1.493 (6)
C1—H1B	0.97	C15—C16	1.512 (6)
C2—C3	1.494 (6)	C15—H15	0.98
C2—H2A	0.97	C16—C17	1.496 (6)
C2—H2B	0.97	C16—C22	1.500 (6)
C3—C4	1.508 (6)	C16—H16	0.98
C3—H3A	0.98	C18—H18A	0.96
C4—C5	1.520 (5)	C18—H18B	0.96
C4—H4A	0.97	C18—H18C	0.96
C4—H4B	0.97	C19—H19A	0.96
C5—C6	1.323 (5)	C19—H19B	0.96
C5—C10	1.514 (6)	C19—H19C	0.96
C6—C7	1.492 (6)	C20—C21	1.493 (6)
C6—H6	0.93	C21—H21A	0.96
C7—C8	1.522 (5)	C21—H21B	0.96
C7—H7	0.98	C21—H21C	0.96
C8—C14	1.529 (5)	C22—H22A	0.97
C8—C9	1.545 (5)	C22—H22B	0.97
C8—H8	0.98	C23—C24	1.473 (8)
C9—C11	1.528 (6)	C23—H23A	0.97
C9—C10	1.559 (5)	C23—H23B	0.97
C9—H9	0.98	C24—H24A	0.97
C10—C19	1.538 (6)	C24—H24B	0.97

C20—O1—C3	117.9 (3)	C12—C13—C17	116.7 (3)
C7—O3—H3	116 (5)	C12—C13—C18	108.5 (3)
C23—O4—C17	108.4 (4)	C17—C13—C18	109.5 (3)
C24—O5—C17	108.5 (4)	C12—C13—C14	105.4 (3)
C2—C1—C10	114.3 (4)	C17—C13—C14	100.7 (3)
C2—C1—H1A	108.7	C18—C13—C14	116.1 (3)
C10—C1—H1A	108.7	C15—C14—C8	122.1 (3)
C2—C1—H1B	108.7	C15—C14—C13	106.1 (3)
C10—C1—H1B	108.7	C8—C14—C13	113.5 (3)
H1A—C1—H1B	107.6	C15—C14—H14	104.5
C3—C2—C1	109.4 (4)	C8—C14—H14	104.5
C3—C2—H2A	109.8	C13—C14—H14	104.5
C1—C2—H2A	109.8	C22—C15—C16	59.9 (3)
C3—C2—H2B	109.8	C22—C15—C14	120.6 (4)
C1—C2—H2B	109.8	C16—C15—C14	106.0 (3)
H2A—C2—H2B	108.2	C22—C15—H15	118.3
O1—C3—C2	107.6 (3)	C16—C15—H15	118.3
O1—C3—C4	109.2 (4)	C14—C15—H15	118.3
C2—C3—C4	111.3 (4)	C17—C16—C22	121.7 (4)
O1—C3—H3A	109.6	C17—C16—C15	107.7 (3)
C2—C3—H3A	109.6	C22—C16—C15	59.4 (3)
C4—C3—H3A	109.6	C17—C16—H16	117.6
C3—C4—C5	111.3 (4)	C22—C16—H16	117.6
C3—C4—H4A	109.4	C15—C16—H16	117.6
C5—C4—H4A	109.4	O4—C17—O5	105.8 (3)
C3—C4—H4B	109.4	O4—C17—C16	115.9 (3)
C5—C4—H4B	109.4	O5—C17—C16	105.7 (4)
H4A—C4—H4B	108.0	O4—C17—C13	112.5 (3)
C6—C5—C10	123.0 (4)	O5—C17—C13	110.8 (3)
C6—C5—C4	120.9 (4)	C16—C17—C13	105.9 (3)
C10—C5—C4	116.1 (3)	C13—C18—H18A	109.5
C5—C6—C7	126.1 (4)	C13—C18—H18B	109.5
C5—C6—H6	116.9	H18A—C18—H18B	109.5
C7—C6—H6	116.9	C13—C18—H18C	109.5
O3—C7—C6	106.5 (4)	H18A—C18—H18C	109.5
O3—C7—C8	113.0 (4)	H18B—C18—H18C	109.5
C6—C7—C8	112.2 (3)	C10—C19—H19A	109.5
O3—C7—H7	108.4	C10—C19—H19B	109.5
C6—C7—H7	108.4	H19A—C19—H19B	109.5
C8—C7—H7	108.4	C10—C19—H19C	109.5
C7—C8—C14	112.1 (3)	H19A—C19—H19C	109.5
C7—C8—C9	110.1 (3)	H19B—C19—H19C	109.5
C14—C8—C9	107.7 (3)	O2—C20—O1	124.1 (4)
C7—C8—H8	109.0	O2—C20—C21	124.1 (5)
C14—C8—H8	109.0	O1—C20—C21	111.8 (4)
C9—C8—H8	109.0	C20—C21—H21A	109.5
C11—C9—C8	113.8 (3)	C20—C21—H21B	109.5
C11—C9—C10	112.6 (3)	H21A—C21—H21B	109.5
C8—C9—C10	112.2 (3)	C20—C21—H21C	109.5
C11—C9—H9	105.8	H21A—C21—H21C	109.5
C8—C9—H9	105.8	H21B—C21—H21C	109.5
C10—C9—H9	105.8	C15—C22—C16	60.7 (3)
C5—C10—C1	108.6 (3)	C15—C22—H22A	117.7
C5—C10—C19	109.4 (3)	C16—C22—H22A	117.7
C1—C10—C19	109.1 (3)	C15—C22—H22B	117.7
C5—C10—C9	109.4 (3)	C16—C22—H22B	117.7
C1—C10—C9	108.9 (3)	H22A—C22—H22B	114.8
C19—C10—C9	111.4 (3)	O4—C23—C24	105.4 (4)
C9—C11—C12	114.5 (4)	O4—C23—H23A	110.7
C9—C11—H11A	108.6	C24—C23—H23A	110.7
C12—C11—H11A	108.6	O4—C23—H23B	110.7
C9—C11—H11B	108.6	C24—C23—H23B	110.7
C12—C11—H11B	108.6	H23A—C23—H23B	108.8
H11A—C11—H11B	107.6	O5—C24—C23	104.8 (4)
C13—C12—C11	109.1 (4)	O5—C24—H24A	110.8
C13—C12—H12A	109.9	C23—C24—H24A	110.8
C11—C12—H12A	109.9	O5—C24—H24B	110.8
C13—C12—H12B	109.9	C23—C24—H24B	110.8
C11—C12—H12B	109.9	H24A—C24—H24B	108.9
H12A—C12—H12B	108.3

C10—C1—C2—C3	−57.8 (5)	C7—C8—C14—C13	179.8 (3)
C20—O1—C3—C2	153.4 (4)	C9—C8—C14—C13	58.5 (4)
C20—O1—C3—C4	−85.7 (4)	C12—C13—C14—C15	156.5 (3)
C1—C2—C3—O1	178.3 (3)	C17—C13—C14—C15	34.8 (4)
C1—C2—C3—C4	58.7 (5)	C18—C13—C14—C15	−83.3 (4)
O1—C3—C4—C5	−174.0 (4)	C12—C13—C14—C8	−66.7 (4)
C2—C3—C4—C5	−55.5 (5)	C17—C13—C14—C8	171.6 (3)
C3—C4—C5—C6	−130.2 (5)	C18—C13—C14—C8	53.5 (5)
C3—C4—C5—C10	50.9 (5)	C8—C14—C15—C22	−90.1 (5)
C10—C5—C6—C7	3.2 (8)	C13—C14—C15—C22	42.0 (5)
C4—C5—C6—C7	−175.6 (4)	C8—C14—C15—C16	−154.2 (4)
C5—C6—C7—O3	134.3 (5)	C13—C14—C15—C16	−22.0 (4)
C5—C6—C7—C8	10.2 (7)	C22—C15—C16—C17	−116.9 (4)
O3—C7—C8—C14	78.9 (4)	C14—C15—C16—C17	−0.4 (4)
C6—C7—C8—C14	−160.7 (4)	C14—C15—C16—C22	116.5 (4)
O3—C7—C8—C9	−161.2 (3)	C23—O4—C17—O5	−16.4 (5)
C6—C7—C8—C9	−40.8 (5)	C23—O4—C17—C16	100.4 (5)
C7—C8—C9—C11	−169.7 (3)	C23—O4—C17—C13	−137.5 (5)
C14—C8—C9—C11	−47.2 (4)	C24—O5—C17—O4	−0.3 (5)
C7—C8—C9—C10	61.0 (4)	C24—O5—C17—C16	−123.8 (4)
C14—C8—C9—C10	−176.4 (3)	C24—O5—C17—C13	121.8 (4)
C6—C5—C10—C1	133.9 (5)	C22—C16—C17—O4	83.8 (5)
C4—C5—C10—C1	−47.2 (5)	C15—C16—C17—O4	148.3 (3)
C6—C5—C10—C19	−107.1 (5)	C22—C16—C17—O5	−159.3 (4)
C4—C5—C10—C19	71.8 (5)	C15—C16—C17—O5	−94.8 (4)
C6—C5—C10—C9	15.1 (6)	C22—C16—C17—C13	−41.7 (5)
C4—C5—C10—C9	−166.0 (3)	C15—C16—C17—C13	22.8 (4)
C2—C1—C10—C5	50.6 (5)	C12—C13—C17—O4	84.0 (4)
C2—C1—C10—C19	−68.5 (5)	C18—C13—C17—O4	−39.7 (4)
C2—C1—C10—C9	169.7 (4)	C14—C13—C17—O4	−162.6 (3)
C11—C9—C10—C5	−176.5 (3)	C12—C13—C17—O5	−34.2 (5)
C8—C9—C10—C5	−46.6 (4)	C18—C13—C17—O5	−157.9 (3)
C11—C9—C10—C1	64.9 (4)	C14—C13—C17—O5	79.2 (4)
C8—C9—C10—C1	−165.1 (3)	C12—C13—C17—C16	−148.4 (4)
C11—C9—C10—C19	−55.4 (5)	C18—C13—C17—C16	87.9 (4)
C8—C9—C10—C19	74.5 (4)	C14—C13—C17—C16	−35.0 (4)
C8—C9—C11—C12	48.1 (5)	C3—O1—C20—O2	2.7 (7)
C10—C9—C11—C12	177.2 (4)	C3—O1—C20—C21	−177.1 (4)
C9—C11—C12—C13	−55.2 (5)	C14—C15—C22—C16	−91.5 (4)
C11—C12—C13—C17	171.8 (4)	C17—C16—C22—C15	92.9 (4)
C11—C12—C13—C18	−64.0 (4)	C17—O4—C23—C24	26.1 (7)
C11—C12—C13—C14	61.0 (4)	C17—O5—C24—C23	15.6 (6)
C7—C8—C14—C15	−51.1 (5)	O4—C23—C24—O5	−25.6 (7)
C9—C8—C14—C15	−172.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O5	0.97	2.51	2.857 (5)	101
C18—H18A···O4	0.96	2.38	2.774 (6)	104

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3β-Acet­oxy-17,17-ethyl­enedi­oxy-15β,16β-methyl­ene-5-androsten-7β-ol

Supporting information

Key indicators

checkCIF/PLATON results

3β-Acetoxy-17,17-ethylenedioxy-15β,16β-methylene-5-androsten-7β-ol