Dysobinin, a tetranortriterpenoid

The planar furan ring in the title compound (6[beta]-acetoxy­aza­dirone, C₃₀H₃₈O₆) is twisted with respect to the steroid D ring. The crystal structure is stabilized by C-H...O hydrogen bonds and van der Waals interactions.

Computing details

Data collection: CAD-4-MACH/PC (Enraf-Nonius, 1993); cell refinement: CAD-4-MACH/PC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: NRCVAX; software used to prepare material for publication: SHELXL97.

6β-acetoxyazadirone

Crystal data

C30H38O6	Dx = 1.205 Mg m^−3
Mr = 494.60	Melting point = 185–187 K
Orthorhombic, P21212	Mo Kα radiation, λ = 0.7093 Å
a = 12.426 (3) Å	Cell parameters from 25 reflections
b = 29.446 (10) Å	θ = 5.8–10.0°
c = 7.450 (9) Å	µ = 0.08 mm^−1
V = 2726 (3) Å^3	T = 293 K
Z = 4	Block, colourless
F(000) = 1064	0.3 × 0.25 × 0.2 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.050
Radiation source: fine-focus sealed tube	θmax = 24.9°, θmin = 2.1°
Graphite monochromator	h = 0→13
ω–2θ scans	k = 0→31
4725 measured reflections	l = −8→8
2658 independent reflections	3 standard reflections every 60 min
1552 reflections with I > 2σ(I)	intensity decay: <0.5%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0716P)^2] where P = (Fo^2 + 2Fc^2)/3
2658 reflections	(Δ/σ)max = 0.004
332 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.22 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.

The structure was solved by direct methods and refined anisotropically on non-H atoms by using full-matrix least-squares methods. All the H-atoms were placed in idealized positioned geometrically and allowed to ride with the parent atom to which each was bonded for the final cycles of refinement.

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

	x	y	z	Uiso*/Ueq
C1	0.5522 (4)	0.20231 (14)	−0.4011 (7)	0.0530 (12)
H1	0.5952	0.2074	−0.5014	0.064*
C2	0.4454 (4)	0.20615 (15)	−0.4158 (7)	0.0560 (13)
H2	0.4154	0.2132	−0.5268	0.067*
C3	0.3757 (4)	0.19959 (15)	−0.2635 (7)	0.0505 (12)
C4	0.4114 (3)	0.16855 (13)	−0.1116 (6)	0.0434 (10)
C5	0.5318 (3)	0.15358 (13)	−0.1361 (6)	0.0369 (10)
H5	0.5299	0.1282	−0.2211	0.044*
C6	0.5859 (3)	0.13497 (13)	0.0319 (5)	0.0366 (10)
H6	0.5976	0.1600	0.1164	0.044*
C7	0.6929 (3)	0.11292 (13)	−0.0093 (6)	0.0386 (10)
H7	0.7246	0.1010	0.1015	0.046*
C8	0.7723 (3)	0.14516 (13)	−0.1002 (5)	0.0378 (10)
C9	0.7167 (3)	0.16775 (13)	−0.2628 (6)	0.0408 (10)
H9	0.7006	0.1425	−0.3439	0.049*
C10	0.6047 (3)	0.18990 (12)	−0.2243 (6)	0.0395 (10)
C11	0.7943 (4)	0.19789 (15)	−0.3699 (7)	0.0567 (13)
H11A	0.7641	0.2030	−0.4882	0.068*
H11B	0.7993	0.2272	−0.3107	0.068*
C12	0.9079 (4)	0.17854 (15)	−0.3914 (8)	0.0595 (13)
H12A	0.9315	0.1837	−0.5138	0.071*
H12B	0.9561	0.1951	−0.3127	0.071*
C13	0.9177 (3)	0.12814 (14)	−0.3503 (6)	0.0436 (11)
C14	0.8701 (3)	0.11853 (15)	−0.1653 (6)	0.0429 (11)
C15	0.9288 (3)	0.08938 (17)	−0.0770 (7)	0.0612 (14)
H15	0.9113	0.0787	0.0369	0.073*
C16	1.0278 (4)	0.07475 (19)	−0.1786 (7)	0.0665 (14)
H16A	1.0178	0.0453	−0.2345	0.080*
H16B	1.0905	0.0737	−0.1012	0.080*
C17	1.0373 (3)	0.11232 (16)	−0.3181 (6)	0.0514 (12)
H17	1.0744	0.1377	−0.2596	0.062*
C18	0.6104 (4)	0.23541 (13)	−0.1177 (7)	0.0567 (12)
H18A	0.6636	0.2548	−0.1707	0.085*
H18B	0.6294	0.2293	0.0048	0.085*
H18C	0.5415	0.2501	−0.1215	0.085*
C19	0.8142 (4)	0.17862 (15)	0.0437 (7)	0.0533 (13)
H19A	0.7546	0.1948	0.0951	0.080*
H19B	0.8630	0.1998	−0.0108	0.080*
H19C	0.8510	0.1620	0.1362	0.080*
C20	0.8665 (4)	0.09888 (17)	−0.4957 (7)	0.0632 (14)
H20A	0.8705	0.0675	−0.4614	0.095*
H20B	0.9043	0.1033	−0.6068	0.095*
H20C	0.7925	0.1074	−0.5106	0.095*
C21	0.3378 (3)	0.12663 (15)	−0.1320 (7)	0.0563 (13)
H21A	0.2643	0.1355	−0.1132	0.084*
H21B	0.3576	0.1041	−0.0448	0.084*
H21C	0.3457	0.1142	−0.2504	0.084*
C22	0.3872 (4)	0.19110 (16)	0.0708 (7)	0.0580 (13)
H22A	0.4352	0.2162	0.0887	0.087*
H22B	0.3971	0.1693	0.1652	0.087*
H22C	0.3142	0.2018	0.0719	0.087*
C23	0.5317 (4)	0.09469 (16)	0.2938 (6)	0.0491 (12)
C24	0.4538 (5)	0.0605 (2)	0.3631 (9)	0.0865 (19)
H24A	0.4886	0.0418	0.4512	0.130*
H24B	0.4290	0.0419	0.2658	0.130*
H24C	0.3937	0.0758	0.4170	0.130*
C25	0.6823 (4)	0.03282 (16)	−0.0757 (9)	0.0631 (14)
C26	0.6692 (5)	0.00027 (19)	−0.2274 (9)	0.100 (2)
H26A	0.7262	−0.0217	−0.2241	0.151*
H26B	0.6717	0.0165	−0.3391	0.151*
H26C	0.6012	−0.0149	−0.2167	0.151*
C27	1.1592 (5)	0.1305 (2)	−0.5814 (9)	0.093 (2)
H27	1.1677	0.1611	−0.5540	0.112*
C28	1.1738 (5)	0.0660 (3)	−0.7169 (9)	0.093 (2)
H28	1.1937	0.0438	−0.7990	0.111*
C29	1.1116 (4)	0.0592 (2)	−0.5754 (9)	0.0836 (18)
H29	1.0805	0.0317	−0.5421	0.100*
C30	1.1005 (3)	0.10115 (19)	−0.4833 (7)	0.0586 (13)
O1	0.2865 (3)	0.21722 (12)	−0.2605 (5)	0.0750 (11)
O2	0.5170 (2)	0.10160 (9)	0.1151 (4)	0.0449 (7)
O3	0.5977 (3)	0.11443 (13)	0.3781 (5)	0.0717 (10)
O4	0.6716 (2)	0.07566 (9)	−0.1334 (4)	0.0424 (7)
O5	0.6998 (4)	0.02250 (12)	0.0759 (6)	0.0955 (14)
O6	1.2042 (4)	0.1096 (2)	−0.7251 (6)	0.1188 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.064 (3)	0.045 (3)	0.050 (3)	0.014 (2)	0.004 (3)	0.009 (3)
C2	0.063 (3)	0.060 (3)	0.045 (3)	0.022 (2)	−0.008 (3)	0.009 (3)
C3	0.047 (3)	0.046 (3)	0.058 (3)	0.012 (2)	−0.016 (3)	−0.004 (3)
C4	0.044 (2)	0.037 (2)	0.049 (3)	0.0053 (19)	−0.002 (2)	−0.007 (2)
C5	0.041 (2)	0.033 (2)	0.037 (2)	0.0038 (17)	−0.005 (2)	−0.007 (2)
C6	0.039 (2)	0.038 (2)	0.033 (2)	−0.0029 (18)	0.002 (2)	0.000 (2)
C7	0.044 (2)	0.038 (2)	0.033 (2)	0.0011 (19)	−0.007 (2)	−0.001 (2)
C8	0.041 (2)	0.039 (2)	0.034 (2)	−0.0041 (19)	−0.004 (2)	−0.002 (2)
C9	0.049 (2)	0.032 (2)	0.041 (2)	0.0017 (18)	0.000 (2)	0.006 (2)
C10	0.046 (2)	0.029 (2)	0.044 (2)	0.0017 (17)	0.000 (2)	0.003 (2)
C11	0.056 (3)	0.052 (3)	0.063 (3)	0.005 (2)	0.013 (3)	0.015 (3)
C12	0.052 (3)	0.063 (3)	0.064 (3)	−0.007 (2)	0.014 (3)	0.012 (3)
C13	0.043 (2)	0.047 (3)	0.041 (3)	0.001 (2)	−0.002 (2)	0.006 (2)
C14	0.036 (2)	0.052 (3)	0.041 (3)	−0.003 (2)	0.000 (2)	0.004 (2)
C15	0.050 (3)	0.084 (4)	0.049 (3)	0.015 (3)	0.001 (2)	0.020 (3)
C16	0.045 (3)	0.092 (4)	0.062 (3)	0.022 (3)	−0.002 (3)	0.008 (3)
C17	0.042 (2)	0.062 (3)	0.049 (3)	−0.002 (2)	0.002 (2)	−0.006 (3)
C18	0.059 (3)	0.039 (2)	0.072 (3)	0.001 (2)	0.004 (3)	−0.003 (3)
C19	0.047 (3)	0.054 (3)	0.059 (3)	−0.009 (2)	−0.005 (2)	0.002 (2)
C20	0.047 (3)	0.088 (4)	0.054 (3)	0.008 (3)	−0.004 (2)	−0.005 (3)
C21	0.042 (2)	0.062 (3)	0.065 (3)	−0.001 (2)	−0.003 (3)	−0.001 (3)
C22	0.058 (3)	0.054 (3)	0.062 (3)	0.012 (2)	0.004 (3)	−0.010 (3)
C23	0.049 (3)	0.058 (3)	0.041 (3)	0.009 (2)	0.000 (2)	0.005 (3)
C24	0.083 (4)	0.096 (4)	0.081 (4)	−0.001 (3)	0.013 (4)	0.040 (4)
C25	0.061 (3)	0.044 (3)	0.084 (4)	0.000 (2)	−0.012 (3)	0.010 (3)
C26	0.124 (5)	0.049 (3)	0.129 (5)	−0.001 (3)	−0.016 (5)	−0.026 (4)
C27	0.096 (4)	0.093 (4)	0.091 (5)	0.016 (4)	0.043 (4)	0.010 (4)
C28	0.075 (4)	0.136 (6)	0.068 (4)	0.037 (4)	0.016 (4)	−0.027 (5)
C29	0.062 (3)	0.102 (5)	0.087 (5)	0.010 (3)	0.004 (4)	−0.023 (4)
C30	0.038 (2)	0.081 (4)	0.057 (3)	0.001 (3)	0.000 (3)	0.001 (3)
O1	0.057 (2)	0.081 (2)	0.086 (3)	0.0300 (18)	−0.004 (2)	0.011 (2)
O2	0.0440 (16)	0.0502 (16)	0.0404 (18)	−0.0007 (14)	0.0017 (14)	0.0060 (15)
O3	0.075 (2)	0.098 (3)	0.0426 (19)	−0.001 (2)	−0.007 (2)	0.003 (2)
O4	0.0466 (15)	0.0349 (15)	0.0457 (17)	0.0031 (13)	−0.0031 (15)	0.0018 (16)
O5	0.136 (4)	0.058 (2)	0.093 (3)	0.004 (2)	−0.030 (3)	0.031 (2)
O6	0.117 (4)	0.149 (5)	0.091 (3)	0.027 (4)	0.049 (3)	0.014 (4)

Geometric parameters (Å, º)

C1—C2	1.337 (6)	C16—H16A	0.9700
C1—C10	1.514 (6)	C16—H16B	0.9700
C1—H1	0.9300	C17—C30	1.497 (7)
C2—C3	1.440 (7)	C17—H17	0.9800
C2—H2	0.9300	C18—H18A	0.9600
C3—O1	1.225 (5)	C18—H18B	0.9600
C3—C4	1.521 (6)	C18—H18C	0.9600
C4—C22	1.542 (7)	C19—H19A	0.9600
C4—C21	1.544 (6)	C19—H19B	0.9600
C4—C5	1.570 (5)	C19—H19C	0.9600
C5—C6	1.523 (6)	C20—H20A	0.9600
C5—C10	1.548 (5)	C20—H20B	0.9600
C5—H5	0.9800	C20—H20C	0.9600
C6—O2	1.444 (4)	C21—H21A	0.9600
C6—C7	1.510 (5)	C21—H21B	0.9600
C6—H6	0.9800	C21—H21C	0.9600
C7—O4	1.459 (5)	C22—H22A	0.9600
C7—C8	1.527 (5)	C22—H22B	0.9600
C7—H7	0.9800	C22—H22C	0.9600
C8—C14	1.525 (5)	C23—O3	1.185 (5)
C8—C9	1.545 (6)	C23—O2	1.359 (6)
C8—C19	1.547 (6)	C23—C24	1.489 (7)
C9—C11	1.534 (6)	C24—H24A	0.9600
C9—C10	1.564 (6)	C24—H24B	0.9600
C9—H9	0.9800	C24—H24C	0.9600
C10—C18	1.559 (6)	C25—O5	1.189 (6)
C11—C12	1.531 (6)	C25—O4	1.339 (6)
C11—H11A	0.9700	C25—C26	1.491 (8)
C11—H11B	0.9700	C26—H26A	0.9600
C12—C13	1.520 (6)	C26—H26B	0.9600
C12—H12A	0.9700	C26—H26C	0.9600
C12—H12B	0.9700	C27—C30	1.345 (7)
C13—C20	1.523 (6)	C27—O6	1.355 (7)
C13—C14	1.526 (6)	C27—H27	0.9300
C13—C17	1.576 (6)	C28—C29	1.323 (9)
C14—C15	1.304 (6)	C28—O6	1.340 (8)
C15—C16	1.508 (6)	C28—H28	0.9300
C15—H15	0.9300	C29—C30	1.420 (7)
C16—C17	1.522 (7)	C29—H29	0.9300
C2—C1—C10	121.3 (4)	C15—C16—C17	101.5 (4)
C2—C1—H1	119.4	C15—C16—H16A	111.5
C10—C1—H1	119.4	C17—C16—H16A	111.5
C1—C2—C3	121.4 (5)	C15—C16—H16B	111.5
C1—C2—H2	119.3	C17—C16—H16B	111.5
C3—C2—H2	119.3	H16A—C16—H16B	109.3
O1—C3—C2	120.1 (4)	C30—C17—C16	116.3 (4)
O1—C3—C4	120.4 (5)	C30—C17—C13	115.8 (4)
C2—C3—C4	119.4 (4)	C16—C17—C13	104.2 (3)
C3—C4—C22	109.9 (3)	C30—C17—H17	106.6
C3—C4—C21	103.6 (4)	C16—C17—H17	106.6
C22—C4—C21	108.4 (4)	C13—C17—H17	106.6
C3—C4—C5	111.1 (4)	C10—C18—H18A	109.5
C22—C4—C5	114.2 (4)	C10—C18—H18B	109.5
C21—C4—C5	109.2 (3)	H18A—C18—H18B	109.5
C6—C5—C10	109.8 (3)	C10—C18—H18C	109.5
C6—C5—C4	115.2 (3)	H18A—C18—H18C	109.5
C10—C5—C4	114.4 (3)	H18B—C18—H18C	109.5
C6—C5—H5	105.5	C8—C19—H19A	109.5
C10—C5—H5	105.5	C8—C19—H19B	109.5
C4—C5—H5	105.5	H19A—C19—H19B	109.5
O2—C6—C7	108.5 (3)	C8—C19—H19C	109.5
O2—C6—C5	109.6 (3)	H19A—C19—H19C	109.5
C7—C6—C5	112.1 (3)	H19B—C19—H19C	109.5
O2—C6—H6	108.9	C13—C20—H20A	109.5
C7—C6—H6	108.9	C13—C20—H20B	109.5
C5—C6—H6	108.9	H20A—C20—H20B	109.5
O4—C7—C6	107.0 (3)	C13—C20—H20C	109.5
O4—C7—C8	107.7 (3)	H20A—C20—H20C	109.5
C6—C7—C8	113.0 (3)	H20B—C20—H20C	109.5
O4—C7—H7	109.7	C4—C21—H21A	109.5
C6—C7—H7	109.7	C4—C21—H21B	109.5
C8—C7—H7	109.7	H21A—C21—H21B	109.5
C14—C8—C7	109.6 (3)	C4—C21—H21C	109.5
C14—C8—C9	109.1 (3)	H21A—C21—H21C	109.5
C7—C8—C9	109.1 (3)	H21B—C21—H21C	109.5
C14—C8—C19	106.2 (3)	C4—C22—H22A	109.5
C7—C8—C19	107.8 (3)	C4—C22—H22B	109.5
C9—C8—C19	114.8 (3)	H22A—C22—H22B	109.5
C11—C9—C8	112.1 (3)	C4—C22—H22C	109.5
C11—C9—C10	114.4 (3)	H22A—C22—H22C	109.5
C8—C9—C10	115.7 (3)	H22B—C22—H22C	109.5
C11—C9—H9	104.3	O3—C23—O2	122.6 (4)
C8—C9—H9	104.3	O3—C23—C24	126.7 (5)
C10—C9—H9	104.3	O2—C23—C24	110.7 (5)
C1—C10—C5	106.5 (3)	C23—C24—H24A	109.5
C1—C10—C18	104.8 (3)	C23—C24—H24B	109.5
C5—C10—C18	113.8 (4)	H24A—C24—H24B	109.5
C1—C10—C9	108.9 (3)	C23—C24—H24C	109.5
C5—C10—C9	108.1 (3)	H24A—C24—H24C	109.5
C18—C10—C9	114.3 (3)	H24B—C24—H24C	109.5
C12—C11—C9	114.7 (3)	O5—C25—O4	124.3 (5)
C12—C11—H11A	108.6	O5—C25—C26	125.1 (5)
C9—C11—H11A	108.6	O4—C25—C26	110.6 (5)
C12—C11—H11B	108.6	C25—C26—H26A	109.5
C9—C11—H11B	108.6	C25—C26—H26B	109.5
H11A—C11—H11B	107.6	H26A—C26—H26B	109.5
C13—C12—C11	114.6 (4)	C25—C26—H26C	109.5
C13—C12—H12A	108.6	H26A—C26—H26C	109.5
C11—C12—H12A	108.6	H26B—C26—H26C	109.5
C13—C12—H12B	108.6	C30—C27—O6	111.3 (6)
C11—C12—H12B	108.6	C30—C27—H27	124.4
H12A—C12—H12B	107.6	O6—C27—H27	124.4
C12—C13—C20	112.0 (4)	C29—C28—O6	110.3 (6)
C12—C13—C14	109.4 (4)	C29—C28—H28	124.8
C20—C13—C14	112.1 (3)	O6—C28—H28	124.8
C12—C13—C17	113.3 (4)	C28—C29—C30	108.0 (6)
C20—C13—C17	109.5 (4)	C28—C29—H29	126.0
C14—C13—C17	100.0 (3)	C30—C29—H29	126.0
C15—C14—C8	128.6 (4)	C27—C30—C29	104.1 (5)
C15—C14—C13	111.1 (4)	C27—C30—C17	126.2 (5)
C8—C14—C13	120.0 (4)	C29—C30—C17	129.7 (5)
C14—C15—C16	113.0 (4)	C23—O2—C6	116.3 (3)
C14—C15—H15	123.5	C25—O4—C7	119.1 (4)
C16—C15—H15	123.5	C28—O6—C27	106.3 (5)
C10—C1—C2—C3	1.3 (7)	C11—C9—C10—C18	−58.7 (5)
C1—C2—C3—O1	155.5 (5)	C8—C9—C10—C18	73.9 (5)
C1—C2—C3—C4	−27.8 (7)	C8—C9—C11—C12	39.7 (6)
O1—C3—C4—C22	−47.6 (6)	C10—C9—C11—C12	174.0 (4)
C2—C3—C4—C22	135.8 (5)	C9—C11—C12—C13	16.1 (7)
O1—C3—C4—C21	68.0 (5)	C11—C12—C13—C20	72.3 (6)
C2—C3—C4—C21	−108.7 (5)	C11—C12—C13—C14	−52.6 (6)
O1—C3—C4—C5	−174.9 (4)	C11—C12—C13—C17	−163.2 (4)
C2—C3—C4—C5	8.4 (5)	C7—C8—C14—C15	−49.2 (6)
C3—C4—C5—C6	162.1 (3)	C9—C8—C14—C15	−168.6 (5)
C22—C4—C5—C6	37.2 (5)	C19—C8—C14—C15	67.0 (6)
C21—C4—C5—C6	−84.3 (4)	C7—C8—C14—C13	137.1 (4)
C3—C4—C5—C10	33.5 (5)	C9—C8—C14—C13	17.7 (5)
C22—C4—C5—C10	−91.5 (4)	C19—C8—C14—C13	−106.6 (4)
C21—C4—C5—C10	147.1 (4)	C12—C13—C14—C15	−139.5 (4)
C10—C5—C6—O2	179.2 (3)	C20—C13—C14—C15	95.6 (4)
C4—C5—C6—O2	48.2 (4)	C17—C13—C14—C15	−20.4 (5)
C10—C5—C6—C7	−60.3 (4)	C12—C13—C14—C8	35.1 (5)
C4—C5—C6—C7	168.8 (3)	C20—C13—C14—C8	−89.7 (5)
H5—C5—C10—C18	174.8	C17—C13—C14—C8	154.3 (4)
C19—C8—C9—H9	175.6	C8—C14—C15—C16	−172.2 (4)
O2—C6—C7—O4	61.0 (4)	C13—C14—C15—C16	1.9 (6)
C5—C6—C7—O4	−60.2 (4)	C14—C15—C16—C17	18.2 (6)
O2—C6—C7—C8	179.3 (3)	C15—C16—C17—C30	−158.3 (4)
C5—C6—C7—C8	58.2 (4)	C15—C16—C17—C13	−29.5 (5)
O4—C7—C8—C14	−52.6 (4)	C12—C13—C17—C30	−84.4 (6)
C6—C7—C8—C14	−170.5 (3)	C20—C13—C17—C30	41.5 (5)
O4—C7—C8—C9	66.9 (4)	C14—C13—C17—C30	159.4 (4)
C6—C7—C8—C9	−51.0 (4)	C12—C13—C17—C16	146.6 (4)
O4—C7—C8—C19	−167.8 (3)	C20—C13—C17—C16	−87.5 (4)
C6—C7—C8—C19	74.2 (4)	C14—C13—C17—C16	30.3 (4)
C14—C8—C9—C11	−55.8 (4)	O6—C28—C29—C30	−0.3 (7)
C7—C8—C9—C11	−175.6 (3)	O6—C27—C30—C29	0.2 (7)
C19—C8—C9—C11	63.3 (4)	O6—C27—C30—C17	−178.4 (5)
C14—C8—C9—C10	170.5 (3)	C28—C29—C30—C27	0.1 (7)
C7—C8—C9—C10	50.8 (4)	C28—C29—C30—C17	178.6 (5)
C19—C8—C9—C10	−70.3 (4)	C16—C17—C30—C27	−148.6 (5)
C2—C1—C10—C5	39.2 (5)	C13—C17—C30—C27	88.5 (6)
C2—C1—C10—C18	−81.8 (5)	C16—C17—C30—C29	33.2 (7)
C2—C1—C10—C9	155.5 (4)	C13—C17—C30—C29	−89.7 (6)
C6—C5—C10—C1	173.1 (3)	O3—C23—O2—C6	−0.6 (6)
C4—C5—C10—C1	−55.6 (4)	C24—C23—O2—C6	178.5 (4)
C6—C5—C10—C18	−72.0 (4)	C7—C6—O2—C23	81.6 (4)
C4—C5—C10—C18	59.4 (5)	C5—C6—O2—C23	−155.7 (3)
C6—C5—C10—C9	56.2 (4)	O5—C25—O4—C7	6.5 (7)
C4—C5—C10—C9	−172.5 (3)	C26—C25—O4—C7	−173.6 (4)
C11—C9—C10—C1	58.1 (5)	C6—C7—O4—C25	−110.0 (4)
C8—C9—C10—C1	−169.3 (3)	C8—C7—O4—C25	128.3 (4)
C11—C9—C10—C5	173.4 (4)	C29—C28—O6—C27	0.4 (7)
C8—C9—C10—C5	−54.0 (4)	C30—C27—O6—C28	−0.4 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O3^i	0.98	2.57	3.437 (6)	147
C20—H20C···O3^i	0.96	2.57	3.501 (6)	164
C28—H28···O5^ii	0.93	2.54	3.413 (8)	157

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