1-Deacet-oxy-1-oxocaesalmin.

The title compound, C24H30O7, is a diterpenoid isolated from the seeds of Caesalpinia minax. It consists of two cyclo-hexane rings (A and B), one unsaturated six-membered ring (C) and one furan ring (D). The stereochemistry of the ring junctures is A/B trans and B/C trans. Rings A and B have normal chair conformations while C adopts a twisted half-chair conformation due to fusion to the furan ring which is planar [r.m.s. deviation = 0.0009 (2) Å]. In the crystal, hydroxyl O-H⋯Ocarbon-yl hydrogen bonds link the mol-ecules into a chain structure extending along the a-axis direction.

Related literature

For previous isolation of 1-deacet­oxy-1-oxocaesalmin, see: Kalauni et al. (2005 ▶). For the anti­viral activity of similar diterpenoids, see: Jiang et al. (2001 ▶). For the anti­malarial activity of similar diterpenoids, see: Kalauni et al. (2006 ▶). For the anti­tumor activity of similar diterpenoids, see: Ma et al. (2013 ▶). For the stereochemistry of caesalmin C, see: Jiang et al. (2001 ▶).

Experimental

Crystal data

C24H30O7

M = 430.48

Orthorhombic,

a = 6.7744 (1) Å

b = 17.2209 (4) Å

c = 19.1592 (5) Å

V = 2235.14 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.77 mm−1

T = 173 K

0.38 × 0.27 × 0.22 mm

Data collection

Oxford Diffraction Gemini-S ultra Sapphire CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.83, T max = 1.00

4463 measured reflections

3080 independent reflections

2845 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.087

S = 1.05

3080 reflections

287 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Absolute structure: Flack, 1983 ▶: 1031 Friedel pairs

Absolute structure parameter: −0.1 (2)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814011040/zs2299sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011040/zs2299Isup2.hkl

CCDC reference: 1002789

Additional supporting information: crystallographic information; 3D view; checkCIF report

C24H30O7	F(000) = 920
Mr = 430.48	Dx = 1.279 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2218 reflections
a = 6.7744 (1) Å	θ = 4.6–62.6°
b = 17.2209 (4) Å	µ = 0.77 mm−1
c = 19.1592 (5) Å	T = 173 K
V = 2235.14 (8) Å3	Block, colorless
Z = 4	0.38 × 0.27 × 0.22 mm

Oxford Diffraction Gemini-S ultra Sapphire CCD diffractometer	3080 independent reflections
Radiation source: fine-focus sealed tube	2845 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scan	θmax = 62.7°, θmin = 4.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −4→7
Tmin = 0.83, Tmax = 1.00	k = −19→19
4463 measured reflections	l = −21→13

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.203P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.14 e Å−3
3080 reflections	Δρmin = −0.12 e Å−3
287 parameters	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0052 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack, 1983: 1031 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.1 (2)

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.

	x	y	z	Uiso*/Ueq
O1	0.6154 (2)	0.74496 (9)	0.53183 (8)	0.0547 (5)
O2	1.00500 (18)	0.62367 (8)	0.54535 (7)	0.0354 (3)
H2	1.0035	0.6603	0.5180	0.053*
O3	1.0530 (2)	0.45663 (8)	0.55179 (7)	0.0420 (4)
O4	0.8847 (3)	0.34413 (10)	0.55089 (12)	0.0795 (6)
O5	0.9459 (2)	0.45522 (8)	0.69152 (7)	0.0443 (4)
O6	1.2768 (3)	0.46401 (12)	0.69992 (11)	0.0765 (6)
O7	0.3966 (3)	0.73518 (10)	0.77457 (10)	0.0655 (5)
C1'	1.2248 (5)	0.34629 (16)	0.51680 (16)	0.0804 (9)
H1'1	1.2095	0.2916	0.5087	0.121*
H1'2	1.3250	0.3545	0.5515	0.121*
H1'3	1.2627	0.3714	0.4741	0.121*
C2'	1.0337 (4)	0.37944 (13)	0.54191 (13)	0.0546 (6)
C1''	1.1107 (5)	0.35621 (16)	0.75089 (14)	0.0767 (9)
H1'4	1.2374	0.3313	0.7524	0.115*
H1'5	1.0176	0.3228	0.7279	0.115*
H1'6	1.0666	0.3665	0.7976	0.115*
C2''	1.1270 (4)	0.43059 (14)	0.71173 (12)	0.0519 (6)
C1	0.6091 (3)	0.67845 (13)	0.51015 (11)	0.0431 (5)
C2	0.5798 (4)	0.66072 (14)	0.43471 (11)	0.0518 (6)
H2A	0.5468	0.7076	0.4092	0.062*
H2B	0.4736	0.6236	0.4287	0.062*
C3	0.7740 (3)	0.62687 (14)	0.40805 (11)	0.0460 (5)
H3A	0.8746	0.6669	0.4107	0.055*
H3B	0.7578	0.6134	0.3592	0.055*
C4	0.8484 (3)	0.55493 (12)	0.44730 (10)	0.0395 (5)
C5	0.8484 (3)	0.57154 (11)	0.52880 (10)	0.0330 (4)
C6	0.8845 (3)	0.50065 (11)	0.57584 (11)	0.0352 (5)
H6	0.7671	0.4674	0.5758	0.042*
C7	0.9308 (3)	0.52595 (11)	0.65015 (10)	0.0355 (5)
H7	1.0560	0.5544	0.6514	0.043*
C8	0.7674 (3)	0.57465 (12)	0.68305 (11)	0.0367 (5)
H8	0.6597	0.5390	0.6949	0.044*
C9	0.6799 (3)	0.63698 (12)	0.63335 (10)	0.0369 (5)
H9	0.7733	0.6804	0.6320	0.044*
C10	0.6501 (3)	0.60885 (11)	0.55740 (11)	0.0356 (5)
C11	0.4861 (3)	0.66772 (15)	0.66522 (12)	0.0518 (6)
H11A	0.4424	0.7135	0.6401	0.062*
H11B	0.3839	0.6284	0.6618	0.062*
C12	0.5223 (4)	0.68734 (13)	0.73927 (12)	0.0486 (6)
C13	0.6726 (4)	0.66413 (12)	0.77927 (12)	0.0495 (6)
C14	0.8301 (3)	0.61460 (12)	0.75107 (11)	0.0426 (5)
C15	0.6410 (5)	0.70010 (16)	0.84602 (14)	0.0683 (8)
H15	0.7208	0.6954	0.8853	0.082*
C16	0.4758 (5)	0.74136 (17)	0.84077 (15)	0.0755 (9)
H16	0.4211	0.7705	0.8768	0.091*
C17	1.0046 (4)	0.60919 (15)	0.78090 (12)	0.0564 (6)
H17A	1.0315	0.6373	0.8212	0.068*
H17B	1.1010	0.5773	0.7616	0.068*
C18	0.7257 (4)	0.48423 (14)	0.42442 (13)	0.0557 (6)
H18A	0.5886	0.4983	0.4227	0.084*
H18B	0.7438	0.4427	0.4573	0.084*
H18C	0.7680	0.4676	0.3790	0.084*
C19	1.0596 (3)	0.54143 (16)	0.41966 (12)	0.0532 (6)
H19A	1.0580	0.5410	0.3696	0.080*
H19B	1.1079	0.4925	0.4365	0.080*
H19C	1.1443	0.5824	0.4358	0.080*
C20	0.4714 (3)	0.55316 (14)	0.55402 (12)	0.0469 (6)
H20A	0.3513	0.5828	0.5540	0.070*
H20B	0.4731	0.5194	0.5939	0.070*
H20C	0.4786	0.5227	0.5121	0.070*

	U11	U22	U33	U12	U13	U23
O1	0.0695 (11)	0.0417 (9)	0.0530 (9)	0.0148 (8)	0.0001 (9)	0.0065 (8)
O2	0.0329 (7)	0.0355 (7)	0.0378 (7)	−0.0067 (6)	−0.0040 (6)	0.0067 (6)
O3	0.0434 (8)	0.0341 (7)	0.0486 (8)	0.0060 (6)	0.0001 (7)	−0.0012 (7)
O4	0.0966 (15)	0.0402 (10)	0.1016 (15)	−0.0114 (11)	0.0139 (13)	−0.0059 (10)
O5	0.0491 (8)	0.0377 (8)	0.0461 (8)	0.0054 (7)	0.0038 (7)	0.0120 (7)
O6	0.0493 (10)	0.0942 (15)	0.0858 (14)	0.0124 (10)	−0.0027 (10)	0.0337 (13)
O7	0.0731 (12)	0.0582 (10)	0.0650 (11)	0.0128 (9)	0.0214 (10)	−0.0058 (9)
C1'	0.097 (2)	0.0611 (18)	0.083 (2)	0.0382 (17)	−0.0011 (18)	−0.0062 (16)
C2'	0.0810 (18)	0.0343 (12)	0.0484 (13)	0.0089 (13)	−0.0038 (13)	0.0009 (11)
C1''	0.097 (2)	0.0647 (18)	0.0682 (17)	0.0341 (17)	0.0125 (17)	0.0269 (14)
C2''	0.0611 (15)	0.0550 (14)	0.0397 (12)	0.0224 (13)	0.0053 (12)	0.0086 (11)
C1	0.0332 (10)	0.0490 (13)	0.0469 (12)	0.0080 (10)	−0.0011 (10)	0.0077 (11)
C2	0.0526 (13)	0.0573 (14)	0.0456 (13)	0.0102 (12)	−0.0103 (11)	0.0094 (11)
C3	0.0488 (13)	0.0519 (13)	0.0373 (11)	0.0008 (11)	−0.0069 (10)	0.0029 (11)
C4	0.0391 (11)	0.0425 (12)	0.0368 (11)	0.0004 (10)	−0.0038 (9)	−0.0005 (10)
C5	0.0293 (10)	0.0306 (10)	0.0390 (11)	−0.0033 (8)	−0.0031 (8)	0.0011 (9)
C6	0.0320 (10)	0.0317 (10)	0.0418 (11)	−0.0012 (9)	0.0007 (9)	0.0019 (9)
C7	0.0383 (11)	0.0312 (10)	0.0372 (11)	−0.0021 (9)	0.0001 (9)	0.0091 (9)
C8	0.0369 (10)	0.0322 (10)	0.0409 (11)	−0.0016 (9)	0.0028 (9)	0.0053 (9)
C9	0.0370 (11)	0.0338 (11)	0.0400 (11)	0.0015 (9)	0.0010 (9)	0.0028 (9)
C10	0.0305 (10)	0.0366 (11)	0.0396 (11)	0.0010 (9)	−0.0018 (9)	0.0046 (9)
C11	0.0468 (13)	0.0568 (14)	0.0517 (13)	0.0116 (11)	0.0076 (11)	0.0038 (12)
C12	0.0574 (13)	0.0378 (12)	0.0508 (13)	0.0029 (11)	0.0158 (12)	−0.0007 (10)
C13	0.0698 (16)	0.0348 (11)	0.0438 (12)	−0.0012 (12)	0.0095 (12)	0.0010 (10)
C14	0.0543 (13)	0.0367 (11)	0.0368 (11)	−0.0029 (10)	0.0026 (10)	0.0056 (9)
C15	0.104 (2)	0.0528 (15)	0.0483 (14)	0.0038 (17)	0.0083 (16)	−0.0071 (12)
C16	0.108 (2)	0.0606 (17)	0.0575 (17)	0.0113 (18)	0.0218 (18)	−0.0094 (14)
C17	0.0662 (16)	0.0608 (15)	0.0423 (12)	−0.0050 (13)	−0.0025 (12)	−0.0024 (12)
C18	0.0631 (15)	0.0510 (14)	0.0529 (14)	−0.0068 (12)	−0.0073 (13)	−0.0088 (12)
C19	0.0477 (13)	0.0703 (16)	0.0417 (12)	0.0091 (13)	0.0033 (11)	−0.0005 (12)
C20	0.0297 (10)	0.0550 (14)	0.0559 (14)	−0.0018 (10)	−0.0022 (10)	0.0013 (12)

O1—C1	1.219 (3)	C6—C7	1.522 (3)
O2—C5	1.426 (2)	C6—H6	0.9800
O2—H2	0.8200	C7—C8	1.525 (3)
O3—C2'	1.349 (3)	C7—H7	0.9800
O3—C6	1.445 (2)	C8—C14	1.534 (3)
O4—C2'	1.191 (3)	C8—C9	1.552 (3)
O5—C2''	1.355 (3)	C8—H8	0.9800
O5—C7	1.457 (2)	C9—C11	1.542 (3)
O6—C2''	1.188 (3)	C9—C10	1.547 (3)
O7—C12	1.364 (3)	C9—H9	0.9800
O7—C16	1.381 (4)	C10—C20	1.546 (3)
C1'—C2'	1.494 (4)	C11—C12	1.479 (3)
C1'—H1'1	0.9600	C11—H11A	0.9700
C1'—H1'2	0.9600	C11—H11B	0.9700
C1'—H1'3	0.9600	C12—C13	1.336 (3)
C1''—C2''	1.489 (3)	C13—C15	1.437 (3)
C1''—H1'4	0.9600	C13—C14	1.469 (3)
C1''—H1'5	0.9600	C14—C17	1.316 (3)
C1''—H1'6	0.9600	C15—C16	1.329 (4)
C1—C2	1.491 (3)	C15—H15	0.9300
C1—C10	1.527 (3)	C16—H16	0.9300
C2—C3	1.527 (3)	C17—H17A	0.9300
C2—H2A	0.9700	C17—H17B	0.9300
C2—H2B	0.9700	C18—H18A	0.9600
C3—C4	1.534 (3)	C18—H18B	0.9600
C3—H3A	0.9700	C18—H18C	0.9600
C3—H3B	0.9700	C19—H19A	0.9600
C4—C18	1.538 (3)	C19—H19B	0.9600
C4—C19	1.543 (3)	C19—H19C	0.9600
C4—C5	1.587 (3)	C20—H20A	0.9600
C5—C6	1.537 (3)	C20—H20B	0.9600
C5—C10	1.587 (3)	C20—H20C	0.9600
C5—O2—H2	109.5	C7—C8—C14	113.38 (17)
C2'—O3—C6	119.02 (18)	C7—C8—C9	113.82 (16)
C2''—O5—C7	118.75 (17)	C14—C8—C9	108.46 (16)
C12—O7—C16	105.0 (2)	C7—C8—H8	106.9
C2'—C1'—H1'1	109.5	C14—C8—H8	106.9
C2'—C1'—H1'2	109.5	C9—C8—H8	106.9
H1'1—C1'—H1'2	109.5	C11—C9—C10	111.64 (17)
C2'—C1'—H1'3	109.5	C11—C9—C8	108.64 (17)
H1'1—C1'—H1'3	109.5	C10—C9—C8	114.23 (16)
H1'2—C1'—H1'3	109.5	C11—C9—H9	107.3
O4—C2'—O3	124.4 (2)	C10—C9—H9	107.3
O4—C2'—C1'	125.8 (2)	C8—C9—H9	107.3
O3—C2'—C1'	109.7 (2)	C1—C10—C20	108.65 (16)
C2''—C1''—H1'4	109.5	C1—C10—C9	109.61 (16)
C2''—C1''—H1'5	109.5	C20—C10—C9	109.63 (16)
H1'4—C1''—H1'5	109.5	C1—C10—C5	105.48 (16)
C2''—C1''—H1'6	109.5	C20—C10—C5	113.41 (16)
H1'4—C1''—H1'6	109.5	C9—C10—C5	109.94 (15)
H1'5—C1''—H1'6	109.5	C12—C11—C9	108.5 (2)
O6—C2''—O5	124.6 (2)	C12—C11—H11A	110.0
O6—C2''—C1''	125.2 (2)	C9—C11—H11A	110.0
O5—C2''—C1''	110.3 (2)	C12—C11—H11B	110.0
O1—C1—C2	121.8 (2)	C9—C11—H11B	110.0
O1—C1—C10	121.94 (19)	H11A—C11—H11B	108.4
C2—C1—C10	115.99 (19)	C13—C12—O7	111.8 (2)
C1—C2—C3	106.73 (18)	C13—C12—C11	127.5 (2)
C1—C2—H2A	110.4	O7—C12—C11	120.7 (2)
C3—C2—H2A	110.4	C12—C13—C15	105.6 (2)
C1—C2—H2B	110.4	C12—C13—C14	121.1 (2)
C3—C2—H2B	110.4	C15—C13—C14	133.3 (2)
H2A—C2—H2B	108.6	C17—C14—C13	122.3 (2)
C2—C3—C4	115.30 (18)	C17—C14—C8	125.9 (2)
C2—C3—H3A	108.4	C13—C14—C8	111.82 (19)
C4—C3—H3A	108.4	C16—C15—C13	106.8 (3)
C2—C3—H3B	108.4	C16—C15—H15	126.6
C4—C3—H3B	108.4	C13—C15—H15	126.6
H3A—C3—H3B	107.5	C15—C16—O7	110.8 (2)
C3—C4—C18	108.77 (17)	C15—C16—H16	124.6
C3—C4—C19	104.95 (18)	O7—C16—H16	124.6
C18—C4—C19	106.51 (19)	C14—C17—H17A	120.0
C3—C4—C5	109.67 (16)	C14—C17—H17B	120.0
C18—C4—C5	115.01 (18)	H17A—C17—H17B	120.0
C19—C4—C5	111.41 (16)	C4—C18—H18A	109.5
O2—C5—C6	104.55 (15)	C4—C18—H18B	109.5
O2—C5—C10	107.36 (14)	H18A—C18—H18B	109.5
C6—C5—C10	104.72 (15)	C4—C18—H18C	109.5
O2—C5—C4	109.38 (15)	H18A—C18—H18C	109.5
C6—C5—C4	115.69 (16)	H18B—C18—H18C	109.5
C10—C5—C4	114.39 (16)	C4—C19—H19A	109.5
O3—C6—C7	106.61 (16)	C4—C19—H19B	109.5
O3—C6—C5	110.82 (15)	H19A—C19—H19B	109.5
C7—C6—C5	110.73 (16)	C4—C19—H19C	109.5
O3—C6—H6	109.5	H19A—C19—H19C	109.5
C7—C6—H6	109.5	H19B—C19—H19C	109.5
C5—C6—H6	109.5	C10—C20—H20A	109.5
O5—C7—C6	106.51 (15)	C10—C20—H20B	109.5
O5—C7—C8	106.62 (15)	H20A—C20—H20B	109.5
C6—C7—C8	113.25 (17)	C10—C20—H20C	109.5
O5—C7—H7	110.1	H20A—C20—H20C	109.5
C6—C7—H7	110.1	H20B—C20—H20C	109.5
C8—C7—H7	110.1
C6—O3—C2'—O4	0.9 (4)	C2—C1—C10—C20	−61.1 (2)
C6—O3—C2'—C1'	179.70 (19)	O1—C1—C10—C9	4.7 (3)
C7—O5—C2''—O6	2.4 (3)	C2—C1—C10—C9	179.16 (18)
C7—O5—C2''—C1''	−177.83 (18)	O1—C1—C10—C5	−113.6 (2)
O1—C1—C2—C3	111.0 (2)	C2—C1—C10—C5	60.8 (2)
C10—C1—C2—C3	−63.5 (2)	C11—C9—C10—C1	69.0 (2)
C1—C2—C3—C4	56.6 (2)	C8—C9—C10—C1	−167.21 (17)
C2—C3—C4—C18	76.1 (2)	C11—C9—C10—C20	−50.1 (2)
C2—C3—C4—C19	−170.24 (18)	C8—C9—C10—C20	73.6 (2)
C2—C3—C4—C5	−50.5 (2)	C11—C9—C10—C5	−175.44 (17)
C3—C4—C5—O2	−72.5 (2)	C8—C9—C10—C5	−51.7 (2)
C18—C4—C5—O2	164.53 (17)	O2—C5—C10—C1	70.52 (18)
C19—C4—C5—O2	43.2 (2)	C6—C5—C10—C1	−178.73 (16)
C3—C4—C5—C6	169.76 (16)	C4—C5—C10—C1	−51.0 (2)
C18—C4—C5—C6	46.8 (2)	O2—C5—C10—C20	−170.70 (15)
C19—C4—C5—C6	−74.5 (2)	C6—C5—C10—C20	−60.0 (2)
C3—C4—C5—C10	47.9 (2)	C4—C5—C10—C20	67.7 (2)
C18—C4—C5—C10	−75.0 (2)	O2—C5—C10—C9	−47.6 (2)
C19—C4—C5—C10	163.66 (18)	C6—C5—C10—C9	63.17 (19)
C2'—O3—C6—C7	110.59 (19)	C4—C5—C10—C9	−169.14 (16)
C2'—O3—C6—C5	−128.84 (19)	C10—C9—C11—C12	175.38 (18)
O2—C5—C6—O3	−72.25 (18)	C8—C9—C11—C12	48.5 (2)
C10—C5—C6—O3	174.99 (14)	C16—O7—C12—C13	−0.1 (3)
C4—C5—C6—O3	48.1 (2)	C16—O7—C12—C11	−179.3 (2)
O2—C5—C6—C7	45.8 (2)	C9—C11—C12—C13	−17.5 (3)
C10—C5—C6—C7	−66.91 (19)	C9—C11—C12—O7	161.5 (2)
C4—C5—C6—C7	166.20 (16)	O7—C12—C13—C15	0.0 (3)
C2''—O5—C7—C6	105.7 (2)	C11—C12—C13—C15	179.0 (2)
C2''—O5—C7—C8	−133.07 (19)	O7—C12—C13—C14	−177.6 (2)
O3—C6—C7—O5	−64.06 (18)	C11—C12—C13—C14	1.4 (4)
C5—C6—C7—O5	175.31 (15)	C12—C13—C14—C17	159.7 (2)
O3—C6—C7—C8	179.06 (15)	C15—C13—C14—C17	−17.1 (4)
C5—C6—C7—C8	58.4 (2)	C12—C13—C14—C8	−17.9 (3)
O5—C7—C8—C14	75.5 (2)	C15—C13—C14—C8	165.3 (2)
C6—C7—C8—C14	−167.69 (16)	C7—C8—C14—C17	−0.5 (3)
O5—C7—C8—C9	−159.89 (16)	C9—C8—C14—C17	−127.9 (2)
C6—C7—C8—C9	−43.1 (2)	C7—C8—C14—C13	177.05 (17)
C7—C8—C9—C11	166.11 (18)	C9—C8—C14—C13	49.6 (2)
C14—C8—C9—C11	−66.7 (2)	C12—C13—C15—C16	0.2 (3)
C7—C8—C9—C10	40.8 (2)	C14—C13—C15—C16	177.4 (3)
C14—C8—C9—C10	167.97 (16)	C13—C15—C16—O7	−0.3 (3)
O1—C1—C10—C20	124.5 (2)	C12—O7—C16—C15	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	2.04	2.804 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.04	2.804 (2)	156

Symmetry code: (i) .