Maleopimaric acid acetic acid solvate.

The title compound, C(24)H(32)O(5)·C(2)H(4)O(2), is a derivative of abietic acid. The two fused and unbridged cyclo-hexane rings have chair conformations and the anhydride ring is planar. Of the other three six-membered rings, two have boat conformations and one has a twist-boat conformation. The crystal structure is stabilized by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For general background, see: McCoy (2000 ▶); Schweizer et al. (2003 ▶); Savluchinske-Feio et al. (2007 ▶). For the crystal structure of a similar compound, see: Pan et al. (2006 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H32O5·C2H4O2

M = 460.55

Orthorhombic,

a = 7.9469 (10) Å

b = 12.7755 (16) Å

c = 24.884 (3) Å

V = 2526.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.97, T max = 0.98

13853 measured reflections

2837 independent reflections

2432 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.110

S = 1.04

2837 reflections

304 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023745/wn2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023745/wn2334Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H32O5·C2H4O2	Dx = 1.211 Mg m−3
Mr = 460.55	Melting point: 498 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3636 reflections
a = 7.9469 (10) Å	θ = 2.3–23.2°
b = 12.7755 (16) Å	µ = 0.09 mm−1
c = 24.884 (3) Å	T = 291 K
V = 2526.3 (5) Å3	Block, colorless
Z = 4	0.30 × 0.26 × 0.24 mm
F(000) = 992

Bruker SMART APEX CCD diffractometer	2837 independent reflections
Radiation source: sealed tube	2432 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→8
Tmin = 0.97, Tmax = 0.98	k = −15→15
13853 measured reflections	l = −27→30

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.05P)2 + 0.55P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2837 reflections	Δρmax = 0.19 e Å−3
304 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (9)

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 Friedel pairs have been merged in the absence of anomalous scattering.

	x	y	z	Uiso*/Ueq
C1	0.5002 (4)	−0.1408 (3)	0.21013 (13)	0.0419 (7)
C2	0.5980 (4)	−0.0411 (2)	0.20070 (12)	0.0398 (7)
H2	0.6794	−0.0301	0.2297	0.048*
C3	0.6887 (4)	−0.0420 (2)	0.14559 (13)	0.0417 (7)
H3	0.7696	−0.0998	0.1434	0.050*
C4	0.7802 (4)	0.0670 (2)	0.14272 (13)	0.0426 (7)
H4A	0.8616	0.0723	0.1716	0.051*
H4B	0.8400	0.0730	0.1089	0.051*
C5	0.6514 (4)	0.1559 (2)	0.14754 (14)	0.0411 (7)
H5	0.6683	0.1867	0.1832	0.049*
C6	0.4713 (4)	0.1086 (2)	0.14794 (13)	0.0414 (7)
C7	0.4657 (4)	0.0448 (2)	0.20125 (12)	0.0409 (7)
H7	0.4851	0.0916	0.2318	0.049*
C8	0.3020 (4)	−0.0147 (3)	0.20917 (13)	0.0442 (8)
C9	0.4523 (4)	0.0321 (3)	0.10233 (12)	0.0429 (7)
H9	0.3687	0.0390	0.0764	0.052*
C10	0.5648 (4)	−0.0472 (3)	0.10145 (12)	0.0453 (8)
C11	0.5732 (5)	−0.1285 (3)	0.05890 (15)	0.0552 (10)
H11	0.6773	−0.1203	0.0383	0.066*
C12	0.4230 (5)	−0.1334 (3)	0.02054 (15)	0.0553 (10)
H12A	0.3219	−0.1455	0.0407	0.083*
H12B	0.4391	−0.1895	−0.0046	0.083*
H12C	0.4137	−0.0683	0.0015	0.083*
C13	0.5604 (5)	−0.2392 (3)	0.07953 (13)	0.0503 (9)
H13A	0.6437	−0.2503	0.1069	0.075*
H13B	0.5788	−0.2873	0.0505	0.075*
H13C	0.4504	−0.2505	0.0944	0.075*
C14	0.3351 (4)	0.1953 (2)	0.14874 (13)	0.0434 (7)
H14A	0.2267	0.1642	0.1406	0.052*
H14B	0.3287	0.2247	0.1846	0.052*
C15	0.3695 (4)	0.2827 (2)	0.10897 (13)	0.0427 (8)
H15A	0.3630	0.2555	0.0726	0.051*
H15B	0.2849	0.3369	0.1128	0.051*
C16	0.5419 (4)	0.3288 (2)	0.11854 (13)	0.0409 (7)
H16	0.5485	0.3405	0.1574	0.049*
C17	0.5691 (4)	0.4405 (3)	0.09213 (12)	0.0408 (7)
C18	0.7484 (4)	0.4797 (3)	0.10755 (14)	0.0442 (8)
H18A	0.7707	0.5453	0.0893	0.053*
H18B	0.7528	0.4925	0.1459	0.053*
C19	0.8818 (4)	0.4017 (3)	0.09266 (15)	0.0491 (9)
H19A	0.9912	0.4293	0.1026	0.059*
H19B	0.8809	0.3914	0.0540	0.059*
C20	0.8550 (4)	0.2952 (3)	0.12078 (14)	0.0450 (8)
H20A	0.8616	0.3047	0.1594	0.054*
H20B	0.9437	0.2474	0.1102	0.054*
C21	0.6810 (4)	0.2471 (2)	0.10598 (12)	0.0405 (7)
C22	0.6830 (4)	0.2061 (3)	0.04687 (12)	0.0429 (7)
H22A	0.5701	0.1906	0.0357	0.064*
H22B	0.7501	0.1437	0.0449	0.064*
H22C	0.7300	0.2587	0.0238	0.064*
C23	0.5378 (5)	0.4443 (3)	0.03186 (12)	0.0445 (7)
H23A	0.4192	0.4508	0.0252	0.067*
H23B	0.5789	0.3812	0.0156	0.067*
H23C	0.5955	0.5034	0.0168	0.067*
C24	0.4419 (4)	0.5116 (3)	0.11930 (13)	0.0426 (7)
C25	0.1024 (4)	0.6778 (3)	0.18987 (14)	0.0460 (8)
C26	−0.0272 (4)	0.7410 (3)	0.21888 (13)	0.0484 (8)
H26A	−0.0330	0.7187	0.2557	0.073*
H26B	−0.1348	0.7313	0.2021	0.073*
H26C	0.0031	0.8137	0.2175	0.073*
O1	0.5518 (3)	−0.22935 (16)	0.21417 (9)	0.0463 (6)
O2	0.3332 (3)	−0.12062 (18)	0.21447 (10)	0.0472 (6)
O3	0.1594 (3)	0.01506 (17)	0.21128 (9)	0.0453 (5)
O4	0.4493 (3)	0.51827 (17)	0.17031 (8)	0.0455 (6)
H4C	0.3728	0.5602	0.1887	0.055*
O5	0.3379 (3)	0.55953 (19)	0.09249 (8)	0.0472 (6)
O6	0.2043 (3)	0.62457 (17)	0.21453 (9)	0.0465 (6)
O7	0.1034 (3)	0.68154 (18)	0.13804 (9)	0.0462 (6)
H7A	0.1831	0.6430	0.1191	0.055*

	U11	U22	U33	U12	U13	U23
C1	0.0453 (18)	0.0411 (16)	0.0395 (17)	0.0089 (14)	−0.0018 (14)	0.0098 (14)
C2	0.0398 (17)	0.0409 (17)	0.0389 (16)	0.0087 (14)	0.0007 (13)	−0.0023 (13)
C3	0.0443 (17)	0.0377 (15)	0.0431 (17)	0.0077 (14)	0.0041 (15)	0.0005 (13)
C4	0.0427 (17)	0.0423 (17)	0.0428 (17)	0.0049 (14)	0.0031 (14)	0.0012 (14)
C5	0.0417 (17)	0.0386 (16)	0.0430 (17)	0.0036 (13)	0.0036 (15)	−0.0003 (13)
C6	0.0400 (16)	0.0405 (16)	0.0437 (17)	0.0004 (13)	−0.0006 (15)	−0.0001 (14)
C7	0.0403 (17)	0.0403 (16)	0.0420 (17)	0.0049 (14)	−0.0029 (14)	−0.0019 (13)
C8	0.0434 (18)	0.0452 (18)	0.0441 (18)	0.0096 (15)	0.0095 (15)	0.0081 (14)
C9	0.0470 (17)	0.0430 (17)	0.0388 (16)	0.0055 (15)	−0.0113 (15)	−0.0024 (13)
C10	0.0439 (18)	0.0488 (19)	0.0433 (17)	0.0118 (15)	0.0043 (15)	−0.0102 (14)
C11	0.067 (2)	0.0469 (19)	0.051 (2)	0.0168 (19)	−0.0152 (19)	−0.0133 (16)
C12	0.059 (2)	0.050 (2)	0.057 (2)	0.0163 (18)	−0.0149 (19)	−0.0216 (17)
C13	0.0488 (19)	0.056 (2)	0.0461 (19)	−0.0147 (17)	0.0107 (16)	−0.0149 (15)
C14	0.0414 (17)	0.0470 (17)	0.0418 (17)	0.0044 (15)	−0.0055 (15)	0.0019 (14)
C15	0.0506 (19)	0.0365 (16)	0.0411 (17)	0.0070 (15)	−0.0127 (15)	−0.0028 (13)
C16	0.0417 (17)	0.0392 (16)	0.0418 (17)	0.0102 (14)	0.0007 (14)	0.0027 (13)
C17	0.0387 (16)	0.0441 (17)	0.0397 (15)	0.0031 (14)	0.0028 (14)	0.0037 (14)
C18	0.0451 (17)	0.0406 (18)	0.0469 (18)	−0.0079 (15)	0.0056 (15)	0.0080 (14)
C19	0.0444 (18)	0.051 (2)	0.0522 (19)	−0.0018 (15)	0.0170 (16)	0.0135 (16)
C20	0.0445 (18)	0.0445 (18)	0.0459 (18)	−0.0015 (15)	0.0029 (15)	0.0114 (15)
C21	0.0416 (17)	0.0394 (16)	0.0406 (16)	0.0058 (14)	0.0125 (14)	0.0013 (13)
C22	0.0426 (17)	0.0441 (17)	0.0420 (17)	0.0118 (15)	0.0126 (14)	−0.0080 (14)
C23	0.0463 (18)	0.0417 (17)	0.0456 (17)	0.0112 (15)	0.0012 (15)	0.0056 (14)
C24	0.0422 (17)	0.0411 (17)	0.0443 (17)	0.0118 (15)	−0.0131 (14)	−0.0023 (13)
C25	0.0419 (18)	0.0466 (18)	0.0496 (19)	0.0143 (15)	−0.0064 (15)	0.0150 (15)
C26	0.0450 (18)	0.0536 (19)	0.0468 (18)	0.0114 (16)	0.0139 (16)	0.0172 (16)
O1	0.0498 (13)	0.0413 (12)	0.0480 (12)	0.0178 (11)	0.0177 (12)	0.0161 (10)
O2	0.0437 (13)	0.0468 (12)	0.0511 (13)	0.0058 (11)	0.0054 (12)	0.0177 (10)
O3	0.0417 (13)	0.0465 (12)	0.0477 (12)	0.0104 (11)	0.0100 (11)	0.0107 (10)
O4	0.0480 (13)	0.0462 (12)	0.0422 (12)	0.0174 (11)	−0.0129 (11)	−0.0074 (9)
O5	0.0502 (13)	0.0539 (14)	0.0376 (11)	0.0186 (11)	−0.0092 (11)	0.0108 (10)
O6	0.0465 (13)	0.0495 (13)	0.0436 (12)	0.0148 (11)	−0.0067 (11)	0.0144 (10)
O7	0.0442 (13)	0.0469 (12)	0.0475 (13)	0.0169 (10)	−0.0119 (10)	0.0153 (11)

C1—O1	1.207 (4)	C14—H14B	0.9700
C1—O2	1.356 (4)	C15—C16	1.510 (5)
C1—C2	1.511 (5)	C15—H15A	0.9700
C2—C7	1.520 (4)	C15—H15B	0.9700
C2—C3	1.550 (4)	C16—C21	1.552 (4)
C2—H2	0.9800	C16—C17	1.586 (4)
C3—C10	1.477 (5)	C16—H16	0.9800
C3—C4	1.573 (4)	C17—C24	1.518 (5)
C3—H3	0.9800	C17—C23	1.521 (4)
C4—C5	1.533 (4)	C17—C18	1.558 (5)
C4—H4A	0.9700	C18—C19	1.501 (5)
C4—H4B	0.9700	C18—H18A	0.9700
C5—C6	1.553 (4)	C18—H18B	0.9700
C5—C21	1.576 (4)	C19—C20	1.544 (4)
C5—H5	0.9800	C19—H19A	0.9700
C6—C9	1.505 (4)	C19—H19B	0.9700
C6—C14	1.549 (4)	C20—C21	1.557 (5)
C6—C7	1.557 (4)	C20—H20A	0.9700
C7—C8	1.519 (5)	C20—H20B	0.9700
C7—H7	0.9800	C21—C22	1.561 (4)
C8—O3	1.197 (4)	C22—H22A	0.9600
C8—O2	1.382 (4)	C22—H22B	0.9600
C9—C10	1.351 (5)	C22—H22C	0.9600
C9—H9	0.9300	C23—H23A	0.9600
C10—C11	1.485 (4)	C23—H23B	0.9600
C11—C13	1.507 (5)	C23—H23C	0.9600
C11—C12	1.529 (5)	C24—O5	1.226 (4)
C11—H11	0.9800	C24—O4	1.274 (4)
C12—H12A	0.9600	C25—O6	1.223 (4)
C12—H12B	0.9600	C25—O7	1.291 (4)
C12—H12C	0.9600	C25—C26	1.494 (5)
C13—H13A	0.9600	C26—H26A	0.9600
C13—H13B	0.9600	C26—H26B	0.9600
C13—H13C	0.9600	C26—H26C	0.9600
C14—C15	1.517 (4)	O4—H4C	0.9300
C14—H14A	0.9700	O7—H7A	0.9300
O1—C1—O2	120.3 (3)	H14A—C14—H14B	107.8
O1—C1—C2	128.9 (3)	C16—C15—C14	110.3 (3)
O2—C1—C2	110.8 (3)	C16—C15—H15A	109.6
C1—C2—C7	104.6 (3)	C14—C15—H15A	109.6
C1—C2—C3	111.8 (3)	C16—C15—H15B	109.6
C7—C2—C3	109.6 (2)	C14—C15—H15B	109.6
C1—C2—H2	110.3	H15A—C15—H15B	108.1
C7—C2—H2	110.3	C15—C16—C21	110.7 (3)
C3—C2—H2	110.3	C15—C16—C17	114.1 (3)
C10—C3—C2	110.4 (3)	C21—C16—C17	115.1 (3)
C10—C3—C4	108.3 (3)	C15—C16—H16	105.3
C2—C3—C4	104.4 (3)	C21—C16—H16	105.3
C10—C3—H3	111.2	C17—C16—H16	105.3
C2—C3—H3	111.2	C24—C17—C23	108.1 (3)
C4—C3—H3	111.2	C24—C17—C18	107.9 (3)
C5—C4—C3	110.1 (3)	C23—C17—C18	112.5 (3)
C5—C4—H4A	109.6	C24—C17—C16	105.3 (3)
C3—C4—H4A	109.6	C23—C17—C16	114.5 (3)
C5—C4—H4B	109.6	C18—C17—C16	108.2 (3)
C3—C4—H4B	109.6	C19—C18—C17	111.8 (3)
H4A—C4—H4B	108.2	C19—C18—H18A	109.2
C4—C5—C6	109.1 (2)	C17—C18—H18A	109.2
C4—C5—C21	113.4 (3)	C19—C18—H18B	109.2
C6—C5—C21	115.4 (3)	C17—C18—H18B	109.2
C4—C5—H5	106.1	H18A—C18—H18B	107.9
C6—C5—H5	106.1	C18—C19—C20	112.0 (3)
C21—C5—H5	106.1	C18—C19—H19A	109.2
C9—C6—C14	113.8 (3)	C20—C19—H19A	109.2
C9—C6—C5	109.9 (3)	C18—C19—H19B	109.2
C14—C6—C5	111.5 (2)	C20—C19—H19B	109.2
C9—C6—C7	107.5 (3)	H19A—C19—H19B	107.9
C14—C6—C7	110.1 (3)	C19—C20—C21	111.3 (3)
C5—C6—C7	103.6 (3)	C19—C20—H20A	109.4
C8—C7—C2	103.4 (2)	C21—C20—H20A	109.4
C8—C7—C6	113.4 (3)	C19—C20—H20B	109.4
C2—C7—C6	110.5 (3)	C21—C20—H20B	109.4
C8—C7—H7	109.8	H20A—C20—H20B	108.0
C2—C7—H7	109.8	C16—C21—C20	108.6 (3)
C6—C7—H7	109.8	C16—C21—C22	115.0 (3)
O3—C8—O2	118.4 (3)	C20—C21—C22	110.3 (3)
O3—C8—C7	131.1 (3)	C16—C21—C5	105.0 (2)
O2—C8—C7	110.4 (3)	C20—C21—C5	105.6 (3)
C10—C9—C6	115.6 (3)	C22—C21—C5	111.8 (3)
C10—C9—H9	122.2	C21—C22—H22A	109.5
C6—C9—H9	122.2	C21—C22—H22B	109.5
C9—C10—C3	113.3 (3)	H22A—C22—H22B	109.5
C9—C10—C11	124.5 (3)	C21—C22—H22C	109.5
C3—C10—C11	122.1 (3)	H22A—C22—H22C	109.5
C10—C11—C13	114.2 (3)	H22B—C22—H22C	109.5
C10—C11—C12	116.0 (3)	C17—C23—H23A	109.5
C13—C11—C12	97.0 (3)	C17—C23—H23B	109.5
C10—C11—H11	109.7	H23A—C23—H23B	109.5
C13—C11—H11	109.7	C17—C23—H23C	109.5
C12—C11—H11	109.7	H23A—C23—H23C	109.5
C11—C12—H12A	109.5	H23B—C23—H23C	109.5
C11—C12—H12B	109.5	O5—C24—O4	122.7 (3)
H12A—C12—H12B	109.5	O5—C24—C17	120.4 (3)
C11—C12—H12C	109.5	O4—C24—C17	116.9 (3)
H12A—C12—H12C	109.5	O6—C25—O7	121.2 (3)
H12B—C12—H12C	109.5	O6—C25—C26	121.0 (3)
C11—C13—H13A	109.5	O7—C25—C26	117.9 (3)
C11—C13—H13B	109.5	C25—C26—H26A	109.5
H13A—C13—H13B	109.5	C25—C26—H26B	109.5
C11—C13—H13C	109.5	H26A—C26—H26B	109.5
H13A—C13—H13C	109.5	C25—C26—H26C	109.5
H13B—C13—H13C	109.5	H26A—C26—H26C	109.5
C15—C14—C6	113.1 (3)	H26B—C26—H26C	109.5
C15—C14—H14A	109.0	C1—O2—C8	110.7 (3)
C6—C14—H14A	109.0	C24—O4—H4C	119.9
C15—C14—H14B	109.0	C25—O7—H7A	119.5
C6—C14—H14B	109.0
O1—C1—C2—C7	−178.2 (3)	C3—C10—C11—C12	171.8 (3)
O2—C1—C2—C7	1.4 (4)	C9—C6—C14—C15	−79.4 (3)
O1—C1—C2—C3	63.3 (5)	C5—C6—C14—C15	45.5 (4)
O2—C1—C2—C3	−117.1 (3)	C7—C6—C14—C15	159.9 (3)
C1—C2—C3—C10	63.1 (3)	C6—C14—C15—C16	−55.4 (4)
C7—C2—C3—C10	−52.4 (3)	C14—C15—C16—C21	66.0 (3)
C1—C2—C3—C4	179.3 (3)	C14—C15—C16—C17	−162.3 (3)
C7—C2—C3—C4	63.8 (3)	C15—C16—C17—C24	62.4 (3)
C10—C3—C4—C5	58.8 (3)	C21—C16—C17—C24	−168.1 (3)
C2—C3—C4—C5	−58.8 (3)	C15—C16—C17—C23	−56.2 (4)
C3—C4—C5—C6	−5.6 (4)	C21—C16—C17—C23	73.3 (4)
C3—C4—C5—C21	−135.8 (3)	C15—C16—C17—C18	177.5 (3)
C4—C5—C6—C9	−48.9 (3)	C21—C16—C17—C18	−53.0 (3)
C21—C5—C6—C9	80.1 (3)	C24—C17—C18—C19	167.7 (3)
C4—C5—C6—C14	−176.0 (3)	C23—C17—C18—C19	−73.2 (4)
C21—C5—C6—C14	−47.0 (4)	C16—C17—C18—C19	54.3 (3)
C4—C5—C6—C7	65.7 (3)	C17—C18—C19—C20	−59.5 (4)
C21—C5—C6—C7	−165.3 (3)	C18—C19—C20—C21	59.2 (4)
C1—C2—C7—C8	−1.8 (3)	C15—C16—C21—C20	−175.5 (3)
C3—C2—C7—C8	118.1 (3)	C17—C16—C21—C20	53.2 (3)
C1—C2—C7—C6	−123.5 (3)	C15—C16—C21—C22	60.3 (4)
C3—C2—C7—C6	−3.5 (4)	C17—C16—C21—C22	−70.9 (4)
C9—C6—C7—C8	−60.5 (3)	C15—C16—C21—C5	−62.9 (3)
C14—C6—C7—C8	64.0 (3)	C17—C16—C21—C5	165.8 (3)
C5—C6—C7—C8	−176.7 (2)	C19—C20—C21—C16	−54.0 (3)
C9—C6—C7—C2	55.1 (3)	C19—C20—C21—C22	72.8 (3)
C14—C6—C7—C2	179.5 (3)	C19—C20—C21—C5	−166.2 (3)
C5—C6—C7—C2	−61.2 (3)	C4—C5—C21—C16	−178.6 (3)
C2—C7—C8—O3	−178.1 (4)	C6—C5—C21—C16	54.4 (3)
C6—C7—C8—O3	−58.4 (5)	C4—C5—C21—C20	−63.9 (3)
C2—C7—C8—O2	1.8 (3)	C6—C5—C21—C20	169.2 (3)
C6—C7—C8—O2	121.5 (3)	C4—C5—C21—C22	56.1 (4)
C14—C6—C9—C10	−177.5 (3)	C6—C5—C21—C22	−70.9 (3)
C5—C6—C9—C10	56.7 (4)	C23—C17—C24—O5	0.2 (4)
C7—C6—C9—C10	−55.3 (4)	C18—C17—C24—O5	122.0 (3)
C6—C9—C10—C3	−1.2 (4)	C16—C17—C24—O5	−122.7 (3)
C6—C9—C10—C11	−177.3 (3)	C23—C17—C24—O4	−180.0 (3)
C2—C3—C10—C9	57.3 (4)	C18—C17—C24—O4	−58.1 (4)
C4—C3—C10—C9	−56.4 (4)	C16—C17—C24—O4	57.2 (4)
C2—C3—C10—C11	−126.5 (3)	O1—C1—O2—C8	179.4 (3)
C4—C3—C10—C11	119.8 (4)	C2—C1—O2—C8	−0.2 (4)
C9—C10—C11—C13	−124.0 (4)	O3—C8—O2—C1	178.9 (3)
C3—C10—C11—C13	60.1 (5)	C7—C8—O2—C1	−1.1 (4)
C9—C10—C11—C12	−12.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4C···O6	0.93	1.70	2.617 (3)	169
O7—H7A···O5	0.93	1.76	2.681 (3)	171
C13—H13C···O5i	0.96	2.59	3.137 (5)	117
C26—H26B···O1ii	0.96	2.56	3.369 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4C⋯O6	0.93	1.70	2.617 (3)	169
O7—H7A⋯O5	0.93	1.76	2.681 (3)	171
C13—H13C⋯O5i	0.96	2.59	3.137 (5)	117
C26—H26B⋯O1ii	0.96	2.56	3.369 (4)	142

Symmetry codes: (i) ; (ii) .