16α,17-Epoxy-4-pregnene-3,20-dione

Wang, S.; Wang, Y.; Nie, Q.; Zhou, L.; Wu, J.

doi:10.1107/S1600536804029095

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16α,17-Epoxy-4-pregnene-3,20-dione

S. Wang, Y. Wang, Q. Nie, L. Zhou and J. Wu

The title compound, C₂₁H₂₈O₃, is a steroid derivative used as an intermediate in medicine. The molecular structure corresponds to an earlier determination [Goubitz et al. (1984). Steroids, 44, 153–158]. However, the orthorhombic unit-cell parameters of the two determinations are significantly different, and these structures are polymorphs.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029095/cv6409sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029095/cv6409Isup2.hkl Contains datablock I

CCDC reference: 259583

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.038
wR factor = 0.092
Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.73 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C16     ..       5.46 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C17     ..       5.40 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       5.06 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       5.05 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.09 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       5.20 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         O2
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C20
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C21

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           27.48
           From the CIF: _reflns_number_total               2380
           Count of symmetry unique reflns         2384
           Completeness (_total/calc)             99.83%
           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

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 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
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

16α,17-epoxy-4-pregnene-3,20-dione top

Crystal data top

C₂₁H₂₈O₃	D_x = 1.204 Mg m⁻³
M_r = 328.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 16882 reflections
a = 7.3357 (1) Å	θ = 2.0–27.5°
b = 12.1537 (2) Å	µ = 0.08 mm⁻¹
c = 20.3204 (1) Å	T = 293 K
V = 1811.68 (4) Å³	Block, colorless
Z = 4	0.73 × 0.40 × 0.31 mm
F(000) = 712

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2380 independent reflections
Radiation source: retating anode	1311 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
oscillation scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→9
T_min = 0.945, T_max = 0.976	k = −14→15
16882 measured reflections	l = −25→26

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0442P)²] where P = (F_o² + 2F_c²)/3
S = 0.83	(Δ/σ)_max = 0.001
2380 reflections	Δρ_max = 0.14 e Å⁻³
218 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (2)

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.

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.4158 (5)	0.77332 (17)	0.34341 (11)	0.1372 (9)
O2	0.4033 (3)	0.02549 (14)	0.50258 (8)	0.0948 (6)
O3	−0.0240 (4)	−0.0678 (2)	0.45860 (15)	0.1487 (11)
C3	0.3715 (6)	0.6768 (3)	0.33546 (13)	0.0973 (10)
C4	0.5035 (4)	0.5912 (3)	0.32515 (12)	0.0842 (8)
H4A	0.6252	0.6118	0.3213	0.101*
C5	0.4643 (3)	0.4843 (2)	0.32066 (10)	0.0659 (6)
C6	0.6073 (3)	0.4026 (2)	0.30313 (12)	0.0778 (7)
H6A	0.7258	0.4378	0.3054	0.093*
H6B	0.5884	0.3786	0.2581	0.093*
C7	0.6071 (3)	0.3026 (2)	0.34798 (12)	0.0719 (7)
H7A	0.6919	0.2483	0.3310	0.086*
H7B	0.6481	0.3241	0.3915	0.086*
C8	0.4189 (3)	0.25162 (17)	0.35307 (9)	0.0533 (5)
H8A	0.3825	0.2244	0.3096	0.064*
C14	0.4148 (3)	0.15726 (17)	0.40137 (9)	0.0551 (5)
H14A	0.4403	0.1905	0.4443	0.066*
C15	0.5467 (3)	0.0608 (2)	0.39586 (15)	0.0819 (8)
H15A	0.5515	0.0325	0.3512	0.098*
H15B	0.6685	0.0815	0.4097	0.098*
C16	0.4644 (4)	−0.0211 (2)	0.44183 (14)	0.0834 (8)
H16A	0.5038	−0.0981	0.4403	0.100*
C17	0.2700 (3)	0.0053 (2)	0.45194 (11)	0.0676 (6)
C13	0.2270 (3)	0.10261 (19)	0.40878 (9)	0.0532 (5)
C12	0.0992 (3)	0.18906 (19)	0.43530 (11)	0.0689 (6)
H12A	0.1392	0.2115	0.4788	0.083*
H12B	−0.0223	0.1583	0.4393	0.083*
C11	0.0934 (3)	0.28926 (19)	0.38992 (12)	0.0689 (6)
H11A	0.0171	0.3452	0.4099	0.083*
H11B	0.0375	0.2681	0.3486	0.083*
C9	0.2813 (3)	0.33877 (18)	0.37578 (9)	0.0535 (5)
H9A	0.3267	0.3659	0.4181	0.064*
C10	0.2728 (3)	0.4407 (2)	0.32986 (11)	0.0628 (6)
C1	0.1540 (4)	0.5286 (2)	0.36257 (13)	0.0896 (8)
H1A	0.0270	0.5074	0.3585	0.107*
H1B	0.1831	0.5316	0.4091	0.107*
C2	0.1791 (5)	0.6433 (3)	0.33289 (17)	0.1083 (11)
H2A	0.1379	0.6430	0.2875	0.130*
H2B	0.1055	0.6959	0.3571	0.130*
C20	0.1340 (5)	−0.0789 (2)	0.47311 (14)	0.0902 (8)
C21	0.1963 (5)	−0.1744 (2)	0.51246 (16)	0.1193 (11)
H21A	0.0942	−0.2211	0.5222	0.179*
H21B	0.2498	−0.1489	0.5528	0.179*
H21C	0.2854	−0.2152	0.4879	0.179*
C19	0.1572 (4)	0.0554 (2)	0.34354 (11)	0.0766 (7)
H19A	0.0400	0.0222	0.3503	0.115*
H19B	0.2413	0.0010	0.3277	0.115*
H19C	0.1467	0.1135	0.3118	0.115*
C18	0.1973 (3)	0.4112 (2)	0.26136 (11)	0.0861 (8)
H18A	0.1940	0.4761	0.2344	0.129*
H18B	0.0763	0.3820	0.2658	0.129*
H18C	0.2746	0.3571	0.2412	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.210 (3)	0.0731 (14)	0.1289 (17)	−0.0162 (19)	0.005 (2)	0.0094 (12)
O2	0.1237 (15)	0.0796 (11)	0.0812 (11)	−0.0144 (12)	−0.0336 (12)	0.0105 (10)
O3	0.0997 (17)	0.1197 (19)	0.227 (3)	−0.0372 (17)	−0.0011 (19)	0.047 (2)
C3	0.139 (3)	0.079 (2)	0.0743 (17)	−0.012 (2)	0.003 (2)	0.0151 (17)
C4	0.098 (2)	0.084 (2)	0.0705 (16)	−0.0138 (18)	0.0029 (15)	0.0135 (16)
C5	0.0709 (16)	0.0759 (17)	0.0508 (12)	−0.0064 (15)	0.0009 (11)	0.0091 (12)
C6	0.0609 (14)	0.0926 (19)	0.0799 (15)	−0.0125 (16)	0.0108 (14)	0.0137 (16)
C7	0.0478 (13)	0.0842 (17)	0.0838 (15)	−0.0026 (13)	0.0062 (13)	0.0095 (14)
C8	0.0413 (11)	0.0703 (14)	0.0482 (10)	0.0006 (11)	−0.0003 (10)	−0.0036 (10)
C14	0.0495 (12)	0.0634 (13)	0.0525 (11)	0.0014 (12)	−0.0088 (10)	−0.0035 (11)
C15	0.0527 (14)	0.0791 (17)	0.114 (2)	0.0088 (14)	−0.0043 (14)	0.0069 (16)
C16	0.0855 (19)	0.0655 (16)	0.0991 (19)	0.0028 (16)	−0.0130 (16)	0.0047 (16)
C17	0.0742 (16)	0.0648 (16)	0.0638 (13)	−0.0080 (14)	−0.0080 (13)	−0.0078 (12)
C13	0.0470 (11)	0.0585 (13)	0.0540 (11)	−0.0048 (11)	0.0000 (10)	−0.0085 (11)
C12	0.0596 (14)	0.0717 (15)	0.0754 (13)	−0.0079 (13)	0.0191 (13)	−0.0066 (13)
C11	0.0504 (13)	0.0699 (15)	0.0864 (15)	0.0089 (13)	0.0151 (13)	−0.0043 (13)
C9	0.0480 (12)	0.0637 (13)	0.0488 (10)	0.0003 (11)	0.0006 (10)	−0.0032 (11)
C10	0.0578 (14)	0.0714 (16)	0.0591 (12)	0.0043 (13)	−0.0005 (11)	0.0023 (12)
C1	0.089 (2)	0.0743 (17)	0.1055 (19)	0.0144 (16)	0.0167 (16)	0.0094 (17)
C2	0.135 (3)	0.080 (2)	0.110 (2)	0.024 (2)	0.012 (2)	0.0144 (18)
C20	0.101 (2)	0.0702 (18)	0.0991 (18)	−0.015 (2)	0.0122 (18)	0.0003 (17)
C21	0.153 (3)	0.082 (2)	0.123 (2)	−0.013 (2)	0.023 (2)	0.024 (2)
C19	0.0758 (17)	0.0821 (17)	0.0718 (14)	−0.0101 (14)	−0.0144 (13)	−0.0178 (13)
C18	0.0789 (16)	0.107 (2)	0.0729 (15)	0.0031 (17)	−0.0228 (13)	0.0195 (16)

Geometric parameters (Å, º) top

O1—C3	1.228 (4)	C17—C13	1.505 (3)
O2—C16	1.430 (3)	C13—C12	1.508 (3)
O2—C17	1.441 (3)	C13—C19	1.532 (3)
O3—C20	1.204 (4)	C12—C11	1.528 (3)
C3—C4	1.437 (4)	C12—H12A	0.9700
C3—C2	1.470 (4)	C12—H12B	0.9700
C4—C5	1.333 (4)	C11—C9	1.531 (3)
C4—H4A	0.9300	C11—H11A	0.9700
C5—C6	1.488 (3)	C11—H11B	0.9700
C5—C10	1.513 (3)	C9—C10	1.552 (3)
C6—C7	1.520 (3)	C9—H9A	0.9800
C6—H6A	0.9700	C10—C1	1.530 (3)
C6—H6B	0.9700	C10—C18	1.540 (3)
C7—C8	1.516 (3)	C1—C2	1.530 (4)
C7—H7A	0.9700	C1—H1A	0.9700
C7—H7B	0.9700	C1—H1B	0.9700
C8—C14	1.510 (3)	C2—H2A	0.9700
C8—C9	1.534 (3)	C2—H2B	0.9700
C8—H8A	0.9800	C20—C21	1.482 (4)
C14—C15	1.524 (3)	C21—H21A	0.9600
C14—C13	1.537 (3)	C21—H21B	0.9600
C14—H14A	0.9800	C21—H21C	0.9600
C15—C16	1.492 (4)	C19—H19A	0.9600
C15—H15A	0.9700	C19—H19B	0.9600
C15—H15B	0.9700	C19—H19C	0.9600
C16—C17	1.476 (4)	C18—H18A	0.9600
C16—H16A	0.9800	C18—H18B	0.9600
C17—C20	1.493 (4)	C18—H18C	0.9600

C16—O2—C17	61.88 (15)	C13—C12—C11	110.90 (18)
O1—C3—C4	122.2 (4)	C13—C12—H12A	109.5
O1—C3—C2	121.6 (4)	C11—C12—H12A	109.5
C4—C3—C2	116.2 (3)	C13—C12—H12B	109.5
C5—C4—C3	124.7 (3)	C11—C12—H12B	109.5
C5—C4—H4A	117.6	H12A—C12—H12B	108.0
C3—C4—H4A	117.6	C12—C11—C9	113.7 (2)
C4—C5—C6	120.9 (3)	C12—C11—H11A	108.8
C4—C5—C10	122.2 (2)	C9—C11—H11A	108.8
C6—C5—C10	116.8 (2)	C12—C11—H11B	108.8
C5—C6—C7	112.94 (19)	C9—C11—H11B	108.8
C5—C6—H6A	109.0	H11A—C11—H11B	107.7
C7—C6—H6A	109.0	C11—C9—C8	112.17 (18)
C5—C6—H6B	109.0	C11—C9—C10	112.97 (17)
C7—C6—H6B	109.0	C8—C9—C10	113.38 (16)
H6A—C6—H6B	107.8	C11—C9—H9A	105.8
C8—C7—C6	111.62 (19)	C8—C9—H9A	105.8
C8—C7—H7A	109.3	C10—C9—H9A	105.8
C6—C7—H7A	109.3	C5—C10—C1	109.7 (2)
C8—C7—H7B	109.3	C5—C10—C18	107.67 (19)
C6—C7—H7B	109.3	C1—C10—C18	110.5 (2)
H7A—C7—H7B	108.0	C5—C10—C9	108.45 (18)
C14—C8—C7	111.87 (17)	C1—C10—C9	108.61 (17)
C14—C8—C9	108.41 (15)	C18—C10—C9	111.8 (2)
C7—C8—C9	109.73 (18)	C2—C1—C10	113.4 (2)
C14—C8—H8A	108.9	C2—C1—H1A	108.9
C7—C8—H8A	108.9	C10—C1—H1A	108.9
C9—C8—H8A	108.9	C2—C1—H1B	108.9
C8—C14—C15	121.60 (19)	C10—C1—H1B	108.9
C8—C14—C13	114.19 (17)	H1A—C1—H1B	107.7
C15—C14—C13	104.10 (17)	C3—C2—C1	110.7 (3)
C8—C14—H14A	105.2	C3—C2—H2A	109.5
C15—C14—H14A	105.2	C1—C2—H2A	109.5
C13—C14—H14A	105.2	C3—C2—H2B	109.5
C16—C15—C14	102.1 (2)	C1—C2—H2B	109.5
C16—C15—H15A	111.3	H2A—C2—H2B	108.1
C14—C15—H15A	111.3	O3—C20—C21	121.1 (3)
C16—C15—H15B	111.3	O3—C20—C17	119.7 (3)
C14—C15—H15B	111.3	C21—C20—C17	119.1 (3)
H15A—C15—H15B	109.2	C20—C21—H21A	109.5
O2—C16—C17	59.42 (17)	C20—C21—H21B	109.5
O2—C16—C15	113.8 (2)	H21A—C21—H21B	109.5
C17—C16—C15	109.5 (2)	C20—C21—H21C	109.5
O2—C16—H16A	119.8	H21A—C21—H21C	109.5
C17—C16—H16A	119.8	H21B—C21—H21C	109.5
C15—C16—H16A	119.8	C13—C19—H19A	109.5
O2—C17—C16	58.70 (16)	C13—C19—H19B	109.5
O2—C17—C20	111.4 (2)	H19A—C19—H19B	109.5
C16—C17—C20	122.5 (3)	C13—C19—H19C	109.5
O2—C17—C13	115.13 (19)	H19A—C19—H19C	109.5
C16—C17—C13	107.0 (2)	H19B—C19—H19C	109.5
C20—C17—C13	124.5 (2)	C10—C18—H18A	109.5
C17—C13—C12	117.98 (18)	C10—C18—H18B	109.5
C17—C13—C19	106.26 (18)	H18A—C18—H18B	109.5
C12—C13—C19	111.23 (19)	C10—C18—H18C	109.5
C17—C13—C14	102.05 (17)	H18A—C18—H18C	109.5
C12—C13—C14	106.94 (18)	H18B—C18—H18C	109.5
C19—C13—C14	112.13 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O3	0.96	2.50	3.078 (4)	119
C16—H16A···O1ⁱ	0.98	2.60	3.221 (4)	122
C11—H11A···O2ⁱⁱ	0.97	2.52	3.433 (3)	158
C6—H6B···O1ⁱⁱⁱ	0.97	2.43	3.371 (3)	164

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

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