21-Acet­oxy-17α-4-pregnene-3,20-dione

Dey, R.; Chanda, S.; Pal, A.; Roychowdhury, S.

doi:10.1107/S1600536805007415

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21-Acetoxy-17α-4-pregnene-3,20-dione

R. Dey, S. Chanda, A. Pal and S. Roychowdhury

The synthetic steroid 21-acetoxy-17α-4-pregnene-3,20-dione, C₂₃H₃₂O₄, crystallizes with a single molecule in the asymmetric unit. The molecule contains four fused rings, typical of steroids. The cyclohexene ring A has nearly the conformation of a boat. One saturated six-membered ring, B, is intermediate between chair and half-chair conformations, while the other six-membered ring, C, is essentially a chair. The five-membered ring D tends towards a twist conformation. The ring junction A/B is quasi-trans, whereas the ring junctions B/C and C/D are both trans. The molecule is slightly convex towards the β side.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007415/cf6413sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007415/cf6413Isup2.hkl Contains datablock I

CCDC reference: 219638

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.054
wR factor = 0.155
Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.83

Author Response: The data was collected more than 15 years before and we don't have either any crystal or the material to re-crystallize.

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.86

Author Response: The data was collected more than 15 years before and we don't have either any crystal or the material to re-crystallize.


Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.63
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
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           71.04
           From the CIF: _reflns_number_total               1885
           Count of symmetry unique reflns         2272
           Completeness (_total/calc)             82.97%
           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

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

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

Computing details top

Data collection: XDS (Kabsch, 1988); cell refinement: XDS; data reduction: XDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXL97.

21-Acetoxy-17α-4-pregnene-3,20-dione top

Crystal data top

C₂₃H₃₂O₄	F(000) = 808
M_r = 372.49	D_x = 1.212 Mg m⁻³ D_m = 1.23 Mg m⁻³ D_m measured by flotation in benzene/bromoform
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 50 reflections
a = 7.590 (2) Å	θ = 4.0–71.0°
b = 12.098 (3) Å	µ = 0.65 mm⁻¹
c = 22.228 (4) Å	T = 293 K
V = 2041.1 (8) Å³	Parallelepiped, colorless
Z = 4	0.42 × 0.35 × 0.30 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 71.0°, θ_min = 4.0°
Graphite monochromator	h = 0→9
ω–2θ scans	k = 0→14
1885 measured reflections	l = 0→27
1885 independent reflections	3 standard reflections every 150 reflections
1882 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0939P)² + 0.6818P] where P = (F_o² + 2F_c²)/3
1885 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

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
C1	0.1389 (6)	0.0308 (3)	0.5545 (2)	0.0800 (12)
H1A	0.1158	0.0585	0.5143	0.096*
H1B	0.2554	0.0558	0.5662	0.096*
C2	0.1374 (6)	−0.0947 (3)	0.5531 (2)	0.0849 (13)
H2A	0.2215	−0.1205	0.5234	0.102*
H2B	0.1735	−0.1229	0.5920	0.102*
C3	−0.0391 (6)	−0.1380 (3)	0.53824 (17)	0.0743 (10)
O3	−0.0592 (5)	−0.2283 (3)	0.51497 (16)	0.1028 (11)
C4	−0.1875 (6)	−0.0700 (3)	0.5555 (2)	0.0793 (11)
H4	−0.2997	−0.0957	0.5461	0.095*
C5	−0.1749 (5)	0.0280 (3)	0.58421 (18)	0.0683 (9)
C6	−0.3323 (7)	0.0856 (4)	0.6090 (3)	0.1043 (17)
H6A	−0.3355	0.0753	0.6522	0.125*
H6B	−0.4378	0.0524	0.5922	0.125*
C7	−0.3324 (5)	0.2103 (4)	0.5949 (3)	0.0964 (16)
H7A	−0.3416	0.2215	0.5518	0.116*
H7B	−0.4332	0.2451	0.6139	0.116*
C8	−0.1629 (5)	0.2629 (3)	0.61813 (18)	0.0644 (9)
H8	−0.1548	0.2511	0.6617	0.077*
C9	−0.0063 (4)	0.2071 (3)	0.58758 (15)	0.0555 (8)
H9	−0.0244	0.2173	0.5443	0.067*
C10	0.0037 (5)	0.0798 (3)	0.59761 (15)	0.0596 (8)
C11	0.1688 (5)	0.2646 (3)	0.6022 (2)	0.0810 (12)
H11A	0.2002	0.2484	0.6435	0.097*
H11B	0.2601	0.2340	0.5766	0.097*
C12	0.1649 (5)	0.3896 (3)	0.5938 (2)	0.0758 (11)
H12A	0.1529	0.4066	0.5514	0.091*
H12B	0.2753	0.4208	0.6078	0.091*
C13	0.0132 (4)	0.4417 (3)	0.62837 (15)	0.0571 (8)
C14	−0.1553 (5)	0.3866 (3)	0.60524 (18)	0.0637 (9)
H14	−0.1529	0.3941	0.5614	0.076*
C15	−0.3033 (6)	0.4615 (4)	0.6272 (3)	0.0994 (16)
H15A	−0.3392	0.4413	0.6677	0.119*
H15B	−0.4047	0.4566	0.6008	0.119*
C16	−0.2251 (5)	0.5780 (4)	0.6262 (3)	0.0921 (14)
H16A	−0.2421	0.6139	0.6648	0.111*
H16B	−0.2815	0.6223	0.5953	0.111*
C17	−0.0263 (5)	0.5651 (3)	0.61260 (18)	0.0660 (9)
H17	−0.0097	0.5744	0.5692	0.079*
C18	0.0374 (8)	0.4307 (4)	0.69605 (17)	0.0895 (14)
H18A	0.0436	0.3539	0.7067	0.134*
H18B	−0.0605	0.4644	0.7163	0.134*
H18C	0.1445	0.4670	0.7079	0.134*
C19	0.0495 (9)	0.0513 (4)	0.66325 (19)	0.1026 (18)
H19A	−0.0357	0.0844	0.6896	0.154*
H19B	0.1647	0.0792	0.6727	0.154*
H19C	0.0480	−0.0275	0.6684	0.154*
C20	0.0852 (6)	0.6496 (3)	0.64385 (19)	0.0695 (10)
O20	0.0333 (5)	0.7118 (3)	0.68249 (16)	0.0976 (11)
C21	0.2763 (5)	0.6557 (3)	0.6228 (2)	0.0751 (11)
H21A	0.3337	0.5859	0.6315	0.090*
H21B	0.2782	0.6662	0.5796	0.090*
O21	0.3734 (4)	0.7424 (2)	0.65043 (13)	0.0786 (8)
C22	0.4392 (7)	0.7221 (5)	0.7056 (2)	0.0902 (13)
O22	0.4175 (6)	0.6354 (4)	0.73041 (18)	0.1218 (13)
C23	0.5438 (10)	0.8178 (6)	0.7272 (3)	0.133 (2)
H23A	0.5586	0.8127	0.7700	0.200*
H23B	0.4832	0.8852	0.7175	0.200*
H23C	0.6572	0.8176	0.7081	0.200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.063 (2)	0.063 (2)	0.114 (3)	0.0026 (19)	0.004 (2)	−0.013 (2)
C2	0.079 (3)	0.065 (2)	0.111 (3)	0.002 (2)	−0.008 (3)	−0.017 (2)
C3	0.094 (3)	0.0577 (19)	0.071 (2)	−0.005 (2)	−0.011 (2)	−0.0003 (17)
O3	0.121 (3)	0.0721 (19)	0.116 (2)	−0.007 (2)	−0.025 (2)	−0.0190 (17)
C4	0.072 (2)	0.070 (2)	0.096 (3)	−0.010 (2)	−0.008 (2)	−0.004 (2)
C5	0.061 (2)	0.066 (2)	0.078 (2)	−0.0097 (18)	0.0030 (19)	0.0033 (18)
C6	0.071 (3)	0.082 (3)	0.160 (5)	−0.019 (2)	0.028 (3)	−0.016 (3)
C7	0.048 (2)	0.082 (3)	0.159 (5)	−0.005 (2)	0.007 (3)	−0.021 (3)
C8	0.0524 (18)	0.068 (2)	0.073 (2)	−0.0011 (17)	0.0076 (18)	−0.0027 (17)
C9	0.0464 (17)	0.0599 (17)	0.0602 (17)	0.0023 (15)	−0.0011 (16)	−0.0021 (15)
C10	0.061 (2)	0.0593 (17)	0.0587 (17)	−0.0002 (16)	−0.0076 (17)	0.0003 (15)
C11	0.0493 (19)	0.064 (2)	0.130 (4)	0.0031 (17)	−0.006 (2)	−0.025 (2)
C12	0.0502 (19)	0.064 (2)	0.113 (3)	−0.0029 (17)	0.010 (2)	−0.020 (2)
C13	0.0511 (17)	0.0581 (18)	0.0620 (17)	0.0039 (16)	−0.0035 (16)	−0.0046 (14)
C14	0.0472 (17)	0.066 (2)	0.078 (2)	0.0070 (16)	0.0016 (17)	−0.0035 (17)
C15	0.055 (2)	0.084 (3)	0.159 (5)	0.010 (2)	0.015 (3)	−0.021 (3)
C16	0.056 (2)	0.076 (2)	0.145 (4)	0.018 (2)	0.006 (3)	−0.008 (3)
C17	0.0578 (19)	0.064 (2)	0.076 (2)	0.0095 (17)	0.0016 (18)	0.0021 (17)
C18	0.124 (4)	0.076 (2)	0.068 (2)	−0.005 (3)	−0.016 (3)	−0.0002 (19)
C19	0.156 (5)	0.075 (3)	0.077 (3)	0.007 (3)	−0.042 (3)	0.011 (2)
C20	0.072 (2)	0.0567 (19)	0.080 (2)	0.0077 (18)	0.007 (2)	−0.0041 (18)
O20	0.092 (2)	0.086 (2)	0.114 (2)	0.0083 (18)	0.0190 (19)	−0.0350 (18)
C21	0.070 (2)	0.064 (2)	0.092 (3)	−0.0043 (19)	0.009 (2)	−0.016 (2)
O21	0.0780 (18)	0.0650 (15)	0.0928 (19)	−0.0075 (14)	−0.0012 (15)	−0.0088 (13)
C22	0.083 (3)	0.102 (3)	0.086 (3)	0.006 (3)	−0.002 (3)	−0.008 (3)
O22	0.121 (3)	0.131 (3)	0.114 (3)	0.000 (3)	−0.007 (2)	0.028 (2)
C23	0.123 (5)	0.149 (5)	0.128 (5)	−0.023 (4)	−0.020 (4)	−0.048 (4)

Geometric parameters (Å, º) top

C1—C2	1.519 (5)	C12—H12B	0.970
C1—C10	1.524 (6)	C13—C18	1.521 (5)
C1—H1A	0.970	C13—C14	1.531 (5)
C1—H1B	0.970	C13—C17	1.563 (5)
C2—C3	1.476 (6)	C14—C15	1.524 (5)
C2—H2A	0.970	C14—H14	0.980
C2—H2B	0.970	C15—C16	1.530 (7)
C3—O3	1.218 (4)	C15—H15A	0.970
C3—C4	1.446 (6)	C15—H15B	0.970
C4—C5	1.351 (6)	C16—C17	1.547 (5)
C4—H4	0.930	C16—H16A	0.970
C5—C6	1.488 (7)	C16—H16B	0.970
C5—C10	1.522 (5)	C17—C20	1.497 (6)
C6—C7	1.541 (7)	C17—H17	0.980
C6—H6A	0.970	C18—H18A	0.960
C6—H6B	0.970	C18—H18B	0.960
C7—C8	1.525 (6)	C18—H18C	0.960
C7—H7A	0.970	C19—H19A	0.960
C7—H7B	0.970	C19—H19B	0.960
C8—C14	1.525 (5)	C19—H19C	0.960
C8—C9	1.526 (5)	C20—O20	1.208 (5)
C8—H8	0.980	C20—C21	1.526 (6)
C9—C11	1.535 (5)	C21—O21	1.422 (5)
C9—C10	1.558 (5)	C21—H21A	0.970
C9—H9	0.980	C21—H21B	0.970
C10—C19	1.539 (5)	O21—C22	1.346 (6)
C11—C12	1.523 (5)	C22—O22	1.197 (6)
C11—H11A	0.970	C22—C23	1.484 (8)
C11—H11B	0.970	C23—H23A	0.960
C12—C13	1.521 (5)	C23—H23B	0.960
C12—H12A	0.970	C23—H23C	0.960

C2—C1—C10	113.3 (4)	H12A—C12—H12B	108.0
C2—C1—H1A	108.9	C18—C13—C12	111.8 (4)
C10—C1—H1A	108.9	C18—C13—C14	113.3 (3)
C2—C1—H1B	108.9	C12—C13—C14	106.4 (3)
C10—C1—H1B	108.9	C18—C13—C17	109.2 (3)
H1A—C1—H1B	107.7	C12—C13—C17	115.3 (3)
C3—C2—C1	111.5 (4)	C14—C13—C17	100.4 (3)
C3—C2—H2A	109.3	C15—C14—C8	119.7 (4)
C1—C2—H2A	109.3	C15—C14—C13	104.4 (3)
C3—C2—H2B	109.3	C8—C14—C13	113.3 (3)
C1—C2—H2B	109.3	C15—C14—H14	106.2
H2A—C2—H2B	108.0	C8—C14—H14	106.2
O3—C3—C4	121.7 (4)	C13—C14—H14	106.2
O3—C3—C2	121.8 (4)	C14—C15—C16	104.9 (3)
C4—C3—C2	116.5 (3)	C14—C15—H15A	110.8
C5—C4—C3	124.7 (4)	C16—C15—H15A	110.8
C5—C4—H4	117.6	C14—C15—H15B	110.8
C3—C4—H4	117.6	C16—C15—H15B	110.8
C4—C5—C6	121.9 (4)	H15A—C15—H15B	108.8
C4—C5—C10	121.1 (4)	C15—C16—C17	106.8 (3)
C6—C5—C10	116.7 (3)	C15—C16—H16A	110.4
C5—C6—C7	112.6 (4)	C17—C16—H16A	110.4
C5—C6—H6A	109.1	C15—C16—H16B	110.4
C7—C6—H6A	109.1	C17—C16—H16B	110.4
C5—C6—H6B	109.1	H16A—C16—H16B	108.6
C7—C6—H6B	109.1	C20—C17—C16	113.0 (4)
H6A—C6—H6B	107.8	C20—C17—C13	116.1 (3)
C8—C7—C6	109.8 (4)	C16—C17—C13	103.8 (3)
C8—C7—H7A	109.7	C20—C17—H17	107.8
C6—C7—H7A	109.7	C16—C17—H17	107.8
C8—C7—H7B	109.7	C13—C17—H17	107.8
C6—C7—H7B	109.7	C13—C18—H18A	109.5
H7A—C7—H7B	108.2	C13—C18—H18B	109.5
C14—C8—C9	108.7 (3)	H18A—C18—H18B	109.5
C14—C8—C7	112.2 (3)	C13—C18—H18C	109.5
C9—C8—C7	108.8 (3)	H18A—C18—H18C	109.5
C14—C8—H8	109.0	H18B—C18—H18C	109.5
C9—C8—H8	109.0	C10—C19—H19A	109.5
C7—C8—H8	109.0	C10—C19—H19B	109.5
C8—C9—C11	112.3 (3)	H19A—C19—H19B	109.5
C8—C9—C10	114.3 (3)	C10—C19—H19C	109.5
C11—C9—C10	112.1 (3)	H19A—C19—H19C	109.5
C8—C9—H9	105.8	H19B—C19—H19C	109.5
C11—C9—H9	105.8	O20—C20—C17	124.8 (4)
C10—C9—H9	105.8	O20—C20—C21	119.9 (4)
C5—C10—C1	108.5 (3)	C17—C20—C21	115.3 (3)
C5—C10—C19	107.1 (4)	O21—C21—C20	113.4 (3)
C1—C10—C19	111.0 (4)	O21—C21—H21A	108.9
C5—C10—C9	109.6 (3)	C20—C21—H21A	108.9
C1—C10—C9	109.1 (3)	O21—C21—H21B	108.9
C19—C10—C9	111.6 (3)	C20—C21—H21B	108.9
C12—C11—C9	114.1 (3)	H21A—C21—H21B	107.7
C12—C11—H11A	108.7	C22—O21—C21	116.8 (4)
C9—C11—H11A	108.7	O22—C22—O21	122.0 (5)
C12—C11—H11B	108.7	O22—C22—C23	127.4 (5)
C9—C11—H11B	108.7	O21—C22—C23	110.6 (5)
H11A—C11—H11B	107.6	C22—C23—H23A	109.5
C11—C12—C13	111.4 (4)	C22—C23—H23B	109.5
C11—C12—H12A	109.3	H23A—C23—H23B	109.5
C13—C12—H12A	109.3	C22—C23—H23C	109.5
C11—C12—H12B	109.3	H23A—C23—H23C	109.5
C13—C12—H12B	109.3	H23B—C23—H23C	109.5

C10—C1—C2—C3	56.0 (6)	C11—C12—C13—C18	66.5 (5)
C1—C2—C3—O3	154.4 (4)	C11—C12—C13—C14	−57.6 (4)
C1—C2—C3—C4	−28.5 (6)	C11—C12—C13—C17	−168.0 (4)
O3—C3—C4—C5	176.4 (4)	C9—C8—C14—C15	176.1 (4)
C2—C3—C4—C5	−0.7 (6)	C7—C8—C14—C15	55.8 (6)
C3—C4—C5—C6	−170.4 (5)	C9—C8—C14—C13	−60.0 (4)
C3—C4—C5—C10	4.1 (6)	C7—C8—C14—C13	179.7 (3)
C4—C5—C6—C7	−135.7 (5)	C18—C13—C14—C15	72.0 (4)
C10—C5—C6—C7	49.5 (7)	C12—C13—C14—C15	−164.8 (4)
C5—C6—C7—C8	−55.9 (7)	C17—C13—C14—C15	−44.2 (4)
C6—C7—C8—C14	179.8 (4)	C18—C13—C14—C8	−59.9 (4)
C6—C7—C8—C9	59.5 (5)	C12—C13—C14—C8	63.3 (4)
C14—C8—C9—C11	50.3 (4)	C17—C13—C14—C8	−176.2 (3)
C7—C8—C9—C11	172.7 (4)	C8—C14—C15—C16	161.2 (4)
C14—C8—C9—C10	179.4 (3)	C13—C14—C15—C16	33.1 (5)
C7—C8—C9—C10	−58.2 (4)	C14—C15—C16—C17	−8.1 (6)
C4—C5—C10—C1	21.7 (5)	C15—C16—C17—C20	−145.7 (4)
C6—C5—C10—C1	−163.5 (4)	C15—C16—C17—C13	−19.1 (6)
C4—C5—C10—C19	−98.2 (4)	C18—C13—C17—C20	43.8 (5)
C6—C5—C10—C19	76.7 (5)	C12—C13—C17—C20	−83.0 (4)
C4—C5—C10—C9	140.6 (4)	C14—C13—C17—C20	163.1 (3)
C6—C5—C10—C9	−44.6 (5)	C18—C13—C17—C16	−80.9 (4)
C2—C1—C10—C5	−51.1 (5)	C12—C13—C17—C16	152.3 (4)
C2—C1—C10—C19	66.4 (5)	C14—C13—C17—C16	38.4 (4)
C2—C1—C10—C9	−170.4 (4)	C16—C17—C20—O20	10.3 (6)
C8—C9—C10—C5	49.1 (4)	C13—C17—C20—O20	−109.6 (5)
C11—C9—C10—C5	178.3 (3)	C16—C17—C20—C21	−168.5 (4)
C8—C9—C10—C1	167.7 (3)	C13—C17—C20—C21	71.7 (5)
C11—C9—C10—C1	−63.1 (4)	O20—C20—C21—O21	−3.3 (6)
C8—C9—C10—C19	−69.4 (4)	C17—C20—C21—O21	175.5 (3)
C11—C9—C10—C19	59.9 (5)	C20—C21—O21—C22	82.1 (5)
C8—C9—C11—C12	−49.0 (5)	C21—O21—C22—O22	0.0 (7)
C10—C9—C11—C12	−179.2 (4)	C21—O21—C22—C23	177.4 (4)
C9—C11—C12—C13	53.2 (5)

Endocyclic torsion angles (°) about the ring junctions top

Junction	Atoms	Torsion angle	Characteristics
A/B	C4—C5—C10—C1	21.7 (5)°	Quasi-trans
	C6—C5—C10—C9	-44.6 (5)°

B/C	C7—C8—C9—C10	-58.2 (4)°	Trans
	C14—C8—C9—C11	50.3 (4)°

C/D	C12—C13—C14—C8	63.4 (4)°	Trans
	C17—C13—C14—C15	-44.2 (4)°

Functional groups with their orientations, deviations from the C5–C17 mean plane (Å) and angles subtended to the C5–C17 mean plane (°) top

Functional group	Orientation	Deviation	Angle
C18	β-axial	1.894 (4)	87.6 (2)
C19	β-axial	1.678 (4)	79.3 (2)
O3	α-axial	-1.290 (4)	19.5 (2)
O20	β-axial	1.223 (4)	37.5 (3)
C22	β-axial	1.980 (4)	72.4 (2)

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