4-Hy-droxy-methyl-10-meth-oxy-17,22-dioxapenta-cyclo-[21.2.2.2(13,16).1(3,7).0(11,30)]triaconta-1(25),3,5,7(30),8,10,13,15,23,26,28-undeca-ene-2,12-dione acetone monosolvate.

In the title compound, C(30)H(26)O(6)·C(3)H(6)O, the syn-oriented benzoyl groups are nearly parallel to each other; the dihedral angle between their benzene rings is 15.9 (1)°. They form dihedral angles of 72.5 (1) and 84.3 (1)° with the naphthalene system. In the crystal, mol-ecules are linked into a three-dimensional architecture by C-H⋯O and C-H⋯π inter-actions.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For applications of related mol­ecules, see; Okamoto et al. (2012 ▶). For the structures of closely related compounds, see: Hijikata et al. (2010 ▶); Mitsui et al. (2010 ▶); Sasagawa et al. (2011 ▶); Watanabe et al. (2010 ▶).

Experimental

Crystal data

C30H26O6·C3H6O

M = 540.59

Orthorhombic,

a = 15.4948 (3) Å

b = 16.1272 (3) Å

c = 22.4430 (4) Å

V = 5608.23 (18) Å3

Z = 8

Cu Kα radiation

μ = 0.73 mm−1

T = 193 K

0.50 × 0.45 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.712, T max = 0.759

99441 measured reflections

5132 independent reflections

4829 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.05

5132 reflections

366 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010 ▶); program(s) used to solve structure: Il Milione (Burla, et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033521/ld2069sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033521/ld2069Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033521/ld2069Isup3.cml

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

C30H26O6·C3H6O	Dx = 1.280 Mg m−3
Mr = 540.59	Melting point = 537.5–538.8 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 92773 reflections
a = 15.4948 (3) Å	θ = 3.4–68.3°
b = 16.1272 (3) Å	µ = 0.73 mm−1
c = 22.4430 (4) Å	T = 193 K
V = 5608.23 (18) Å3	Block, colorless
Z = 8	0.50 × 0.45 × 0.40 mm
F(000) = 2288

Rigaku R-AXIS RAPID diffractometer	5132 independent reflections
Radiation source: rotating anode	4829 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 10.000 pixels mm-1	θmax = 68.3°, θmin = 3.9°
ω scans	h = −18→18
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −19→19
Tmin = 0.712, Tmax = 0.759	l = −27→27
99441 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0495P)2 + 1.7635P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
5132 reflections	Δρmax = 0.20 e Å−3
366 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/6(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00160 (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.

	x	y	z	Uiso*/Ueq
O1	1.07047 (5)	0.27102 (5)	0.20944 (4)	0.0347 (2)
O2	1.19956 (5)	0.17013 (6)	0.14801 (4)	0.0365 (2)
O3	0.85352 (6)	0.25079 (6)	0.23241 (4)	0.0408 (2)
O4	1.19863 (7)	−0.01523 (6)	0.13445 (5)	0.0546 (3)
O5	0.89572 (6)	0.42949 (5)	−0.01715 (4)	0.0411 (2)
O6	1.01931 (7)	0.19019 (6)	−0.10484 (4)	0.0521 (3)
O1S	0.72978 (11)	0.11706 (9)	0.09895 (8)	0.0950 (5)
C1	0.96632 (7)	0.16581 (7)	0.20049 (5)	0.0284 (2)
C2	0.88697 (8)	0.17239 (7)	0.22823 (5)	0.0324 (3)
C3	0.84625 (8)	0.10363 (8)	0.25505 (5)	0.0378 (3)
H3	0.7913	0.1093	0.2734	0.045*
C4	0.88732 (9)	0.02911 (8)	0.25413 (6)	0.0392 (3)
H4	0.8608	−0.0171	0.2729	0.047*
C5	0.96831 (8)	0.01832 (8)	0.22606 (5)	0.0351 (3)
C6	1.00846 (10)	−0.06012 (8)	0.22537 (6)	0.0434 (3)
H6	0.9814	−0.1052	0.2452	0.052*
C7	1.08489 (10)	−0.07290 (8)	0.19709 (7)	0.0463 (3)
H7	1.1115	−0.1260	0.1978	0.056*
C8	1.12400 (9)	−0.00658 (8)	0.16673 (6)	0.0400 (3)
C9	1.08822 (8)	0.07214 (7)	0.16682 (5)	0.0315 (3)
C10	1.00922 (8)	0.08721 (7)	0.19760 (5)	0.0295 (3)
C11	1.00809 (7)	0.24613 (7)	0.18132 (5)	0.0274 (2)
C12	0.97305 (7)	0.29312 (7)	0.13029 (5)	0.0276 (2)
C13	1.01308 (8)	0.36739 (7)	0.11391 (5)	0.0319 (3)
H13	1.0598	0.3879	0.1371	0.038*
C14	0.98588 (8)	0.41120 (7)	0.06475 (6)	0.0349 (3)
H14	1.0139	0.4614	0.0539	0.042*
C15	0.91706 (8)	0.38176 (7)	0.03089 (5)	0.0328 (3)
C16	0.87467 (8)	0.30933 (8)	0.04747 (6)	0.0341 (3)
H16	0.8264	0.2902	0.0253	0.041*
C17	0.90344 (8)	0.26532 (7)	0.09658 (5)	0.0312 (3)
H17	0.8752	0.2153	0.1074	0.037*
C18	1.13496 (7)	0.13598 (7)	0.12938 (5)	0.0293 (2)
C19	1.10244 (7)	0.15208 (7)	0.06846 (5)	0.0299 (3)
C20	1.13965 (8)	0.21529 (7)	0.03479 (6)	0.0334 (3)
H20	1.1838	0.2483	0.0520	0.040*
C21	1.11380 (8)	0.23109 (8)	−0.02314 (6)	0.0385 (3)
H21	1.1399	0.2744	−0.0455	0.046*
C22	1.04891 (9)	0.18246 (8)	−0.04813 (6)	0.0394 (3)
C23	1.01050 (9)	0.11965 (8)	−0.01486 (6)	0.0414 (3)
H23	0.9659	0.0870	−0.0320	0.050*
C24	1.03688 (8)	0.10465 (7)	0.04282 (6)	0.0361 (3)
H24	1.0103	0.0617	0.0652	0.043*
C25	0.76197 (9)	0.25914 (10)	0.22669 (7)	0.0496 (4)
H25A	0.7472	0.3177	0.2212	0.060*
H25B	0.7339	0.2382	0.2628	0.060*
H25C	0.7421	0.2272	0.1922	0.060*
C26	1.22703 (12)	−0.09660 (10)	0.12000 (10)	0.0656 (5)
H26A	1.1788	−0.1284	0.1034	0.079*
H26B	1.2482	−0.1241	0.1561	0.079*
H26C	1.2737	−0.0934	0.0906	0.079*
C27	0.84853 (8)	0.39230 (9)	−0.06580 (6)	0.0410 (3)
H27A	0.8372	0.4352	−0.0964	0.049*
H27B	0.7921	0.3725	−0.0508	0.049*
C28	0.89555 (9)	0.32062 (9)	−0.09454 (6)	0.0409 (3)
H28A	0.8645	0.3045	−0.1313	0.049*
H28B	0.8942	0.2726	−0.0671	0.049*
C29	0.98906 (9)	0.33975 (9)	−0.11025 (6)	0.0435 (3)
H29A	0.9906	0.3864	−0.1389	0.052*
H29B	1.0199	0.3574	−0.0738	0.052*
C30	1.03545 (11)	0.26622 (10)	−0.13715 (6)	0.0531 (4)
H30A	1.0165	0.2592	−0.1790	0.064*
H30B	1.0983	0.2774	−0.1374	0.064*
C1S	0.73688 (11)	0.04533 (11)	0.11251 (9)	0.0641 (4)
C2S	0.68285 (14)	0.00854 (15)	0.16044 (10)	0.0800 (6)
H2S1	0.7202	−0.0168	0.1906	0.096*
H2S2	0.6450	−0.0339	0.1434	0.096*
H2S3	0.6477	0.0520	0.1789	0.096*
C3S	0.80147 (16)	−0.00945 (16)	0.08399 (14)	0.1037 (8)
H3S1	0.8474	−0.0222	0.1125	0.124*
H3S2	0.8262	0.0186	0.0492	0.124*
H3S3	0.7735	−0.0610	0.0713	0.124*

	U11	U22	U33	U12	U13	U23
O1	0.0305 (4)	0.0346 (4)	0.0390 (5)	−0.0018 (3)	−0.0044 (4)	−0.0020 (3)
O2	0.0293 (4)	0.0451 (5)	0.0350 (5)	−0.0036 (4)	−0.0012 (4)	−0.0012 (4)
O3	0.0337 (5)	0.0391 (5)	0.0494 (5)	−0.0001 (4)	0.0108 (4)	−0.0077 (4)
O4	0.0438 (6)	0.0353 (5)	0.0847 (8)	0.0101 (4)	0.0133 (5)	−0.0011 (5)
O5	0.0472 (5)	0.0364 (5)	0.0398 (5)	−0.0068 (4)	−0.0094 (4)	0.0096 (4)
O6	0.0694 (7)	0.0524 (6)	0.0345 (5)	0.0088 (5)	−0.0144 (5)	−0.0026 (4)
O1S	0.0980 (11)	0.0695 (9)	0.1174 (13)	0.0063 (8)	−0.0003 (10)	0.0117 (9)
C1	0.0308 (6)	0.0314 (6)	0.0229 (5)	−0.0028 (5)	−0.0010 (4)	0.0000 (4)
C2	0.0335 (6)	0.0363 (6)	0.0273 (6)	−0.0032 (5)	0.0012 (5)	−0.0037 (5)
C3	0.0359 (6)	0.0472 (7)	0.0304 (6)	−0.0097 (5)	0.0056 (5)	−0.0015 (5)
C4	0.0458 (7)	0.0416 (7)	0.0302 (6)	−0.0135 (6)	0.0016 (5)	0.0064 (5)
C5	0.0420 (7)	0.0343 (6)	0.0291 (6)	−0.0062 (5)	−0.0040 (5)	0.0051 (5)
C6	0.0535 (8)	0.0325 (6)	0.0441 (7)	−0.0062 (6)	−0.0064 (6)	0.0118 (6)
C7	0.0508 (8)	0.0294 (6)	0.0585 (9)	0.0048 (6)	−0.0075 (7)	0.0076 (6)
C8	0.0361 (7)	0.0342 (6)	0.0497 (8)	0.0037 (5)	−0.0038 (6)	0.0016 (6)
C9	0.0319 (6)	0.0304 (6)	0.0322 (6)	0.0010 (5)	−0.0044 (5)	0.0022 (5)
C10	0.0328 (6)	0.0309 (6)	0.0247 (5)	−0.0023 (5)	−0.0048 (4)	0.0025 (4)
C11	0.0263 (5)	0.0274 (5)	0.0284 (6)	0.0015 (4)	0.0039 (4)	−0.0052 (4)
C12	0.0285 (6)	0.0261 (5)	0.0282 (6)	0.0000 (4)	0.0038 (4)	−0.0022 (4)
C13	0.0323 (6)	0.0307 (6)	0.0326 (6)	−0.0056 (5)	−0.0011 (5)	−0.0026 (5)
C14	0.0393 (7)	0.0287 (6)	0.0367 (6)	−0.0078 (5)	0.0006 (5)	0.0019 (5)
C15	0.0347 (6)	0.0316 (6)	0.0319 (6)	0.0003 (5)	0.0008 (5)	0.0027 (5)
C16	0.0314 (6)	0.0364 (6)	0.0345 (6)	−0.0063 (5)	−0.0037 (5)	0.0005 (5)
C17	0.0328 (6)	0.0285 (6)	0.0325 (6)	−0.0056 (5)	0.0030 (5)	0.0006 (5)
C18	0.0260 (5)	0.0284 (6)	0.0334 (6)	0.0047 (4)	0.0024 (5)	−0.0027 (5)
C19	0.0274 (6)	0.0290 (6)	0.0334 (6)	0.0048 (4)	0.0003 (5)	−0.0021 (5)
C20	0.0288 (6)	0.0340 (6)	0.0373 (6)	0.0015 (5)	−0.0015 (5)	0.0003 (5)
C21	0.0378 (7)	0.0398 (7)	0.0377 (7)	0.0046 (5)	0.0009 (5)	0.0068 (5)
C22	0.0444 (7)	0.0412 (7)	0.0327 (6)	0.0116 (6)	−0.0060 (5)	−0.0047 (5)
C23	0.0449 (7)	0.0357 (7)	0.0436 (7)	0.0001 (6)	−0.0114 (6)	−0.0072 (5)
C24	0.0368 (6)	0.0306 (6)	0.0410 (7)	0.0003 (5)	−0.0035 (5)	−0.0012 (5)
C25	0.0373 (7)	0.0528 (8)	0.0588 (9)	0.0057 (6)	0.0047 (6)	0.0065 (7)
C26	0.0530 (9)	0.0409 (8)	0.1029 (14)	0.0106 (7)	0.0068 (9)	−0.0143 (9)
C27	0.0364 (7)	0.0479 (7)	0.0387 (7)	−0.0037 (6)	−0.0100 (5)	0.0098 (6)
C28	0.0409 (7)	0.0469 (7)	0.0350 (7)	−0.0063 (6)	−0.0092 (5)	0.0073 (6)
C29	0.0406 (7)	0.0512 (8)	0.0388 (7)	−0.0013 (6)	−0.0050 (6)	0.0134 (6)
C30	0.0586 (9)	0.0698 (10)	0.0309 (7)	0.0094 (8)	−0.0038 (6)	0.0079 (7)
C1S	0.0513 (9)	0.0580 (10)	0.0830 (12)	−0.0041 (8)	−0.0127 (9)	−0.0068 (9)
C2S	0.0652 (12)	0.0906 (14)	0.0844 (14)	−0.0182 (10)	−0.0137 (10)	0.0009 (11)
C3S	0.0761 (15)	0.0973 (17)	0.138 (2)	0.0054 (13)	0.0116 (15)	−0.0289 (16)

O1—C11	1.2222 (14)	C17—H17	0.9500
O2—C18	1.2166 (14)	C18—C19	1.4800 (16)
O3—C2	1.3697 (15)	C19—C20	1.3939 (17)
O3—C25	1.4306 (16)	C19—C24	1.3959 (17)
O4—C8	1.3717 (17)	C20—C21	1.3841 (18)
O4—C26	1.4215 (17)	C20—H20	0.9500
O5—C15	1.3654 (15)	C21—C22	1.3930 (19)
O5—C27	1.4445 (16)	C21—H21	0.9500
O6—C22	1.3586 (16)	C22—C23	1.392 (2)
O6—C30	1.4463 (19)	C23—C24	1.3787 (18)
O1S—C1S	1.201 (2)	C23—H23	0.9500
C1—C2	1.3822 (16)	C24—H24	0.9500
C1—C10	1.4328 (16)	C25—H25A	0.9800
C1—C11	1.5107 (15)	C25—H25B	0.9800
C2—C3	1.4109 (17)	C25—H25C	0.9800
C3—C4	1.3600 (19)	C26—H26A	0.9800
C3—H3	0.9500	C26—H26B	0.9800
C4—C5	1.4149 (19)	C26—H26C	0.9800
C4—H4	0.9500	C27—C28	1.511 (2)
C5—C6	1.4098 (19)	C27—H27A	0.9900
C5—C10	1.4297 (16)	C27—H27B	0.9900
C6—C7	1.359 (2)	C28—C29	1.5227 (19)
C6—H6	0.9500	C28—H28A	0.9900
C7—C8	1.4057 (19)	C28—H28B	0.9900
C7—H7	0.9500	C29—C30	1.512 (2)
C8—C9	1.3852 (17)	C29—H29A	0.9900
C9—C10	1.4266 (17)	C29—H29B	0.9900
C9—C18	1.5134 (16)	C30—H30A	0.9900
C11—C12	1.4766 (16)	C30—H30B	0.9900
C12—C17	1.3917 (16)	C1S—C3S	1.481 (3)
C12—C13	1.3980 (16)	C1S—C2S	1.487 (3)
C13—C14	1.3764 (17)	C2S—H2S1	0.9800
C13—H13	0.9500	C2S—H2S2	0.9800
C14—C15	1.3927 (17)	C2S—H2S3	0.9800
C14—H14	0.9500	C3S—H3S1	0.9800
C15—C16	1.3908 (17)	C3S—H3S2	0.9800
C16—C17	1.3846 (17)	C3S—H3S3	0.9800
C16—H16	0.9500
C2—O3—C25	117.13 (10)	C19—C20—H20	119.2
C8—O4—C26	118.39 (12)	C20—C21—C22	118.91 (12)
C15—O5—C27	119.04 (10)	C20—C21—H21	120.5
C22—O6—C30	119.28 (11)	C22—C21—H21	120.5
C2—C1—C10	120.07 (10)	O6—C22—C23	115.15 (12)
C2—C1—C11	116.33 (10)	O6—C22—C21	124.69 (13)
C10—C1—C11	123.16 (10)	C23—C22—C21	120.15 (12)
O3—C2—C1	116.00 (10)	C24—C23—C22	120.31 (12)
O3—C2—C3	121.81 (11)	C24—C23—H23	119.8
C1—C2—C3	121.98 (11)	C22—C23—H23	119.8
C4—C3—C2	118.61 (12)	C23—C24—C19	120.44 (12)
C4—C3—H3	120.7	C23—C24—H24	119.8
C2—C3—H3	120.7	C19—C24—H24	119.8
C3—C4—C5	122.04 (11)	O3—C25—H25A	109.5
C3—C4—H4	119.0	O3—C25—H25B	109.5
C5—C4—H4	119.0	H25A—C25—H25B	109.5
C6—C5—C4	120.45 (12)	O3—C25—H25C	109.5
C6—C5—C10	119.78 (12)	H25A—C25—H25C	109.5
C4—C5—C10	119.77 (11)	H25B—C25—H25C	109.5
C7—C6—C5	121.72 (12)	O4—C26—H26A	109.5
C7—C6—H6	119.1	O4—C26—H26B	109.5
C5—C6—H6	119.1	H26A—C26—H26B	109.5
C6—C7—C8	119.11 (12)	O4—C26—H26C	109.5
C6—C7—H7	120.4	H26A—C26—H26C	109.5
C8—C7—H7	120.4	H26B—C26—H26C	109.5
O4—C8—C9	115.56 (11)	O5—C27—C28	113.35 (10)
O4—C8—C7	122.82 (12)	O5—C27—H27A	108.9
C9—C8—C7	121.61 (13)	C28—C27—H27A	108.9
C8—C9—C10	120.01 (11)	O5—C27—H27B	108.9
C8—C9—C18	115.55 (11)	C28—C27—H27B	108.9
C10—C9—C18	124.31 (10)	H27A—C27—H27B	107.7
C9—C10—C5	117.68 (11)	C27—C28—C29	113.75 (11)
C9—C10—C1	124.80 (10)	C27—C28—H28A	108.8
C5—C10—C1	117.49 (11)	C29—C28—H28A	108.8
O1—C11—C12	121.52 (10)	C27—C28—H28B	108.8
O1—C11—C1	118.25 (10)	C29—C28—H28B	108.8
C12—C11—C1	120.23 (10)	H28A—C28—H28B	107.7
C17—C12—C13	118.49 (11)	C30—C29—C28	112.69 (13)
C17—C12—C11	122.76 (10)	C30—C29—H29A	109.1
C13—C12—C11	118.72 (10)	C28—C29—H29A	109.1
C14—C13—C12	120.98 (11)	C30—C29—H29B	109.1
C14—C13—H13	119.5	C28—C29—H29B	109.1
C12—C13—H13	119.5	H29A—C29—H29B	107.8
C13—C14—C15	119.79 (11)	O6—C30—C29	112.49 (12)
C13—C14—H14	120.1	O6—C30—H30A	109.1
C15—C14—H14	120.1	C29—C30—H30A	109.1
O5—C15—C16	124.78 (11)	O6—C30—H30B	109.1
O5—C15—C14	115.09 (10)	C29—C30—H30B	109.1
C16—C15—C14	120.13 (11)	H30A—C30—H30B	107.8
C17—C16—C15	119.44 (11)	O1S—C1S—C3S	121.8 (2)
C17—C16—H16	120.3	O1S—C1S—C2S	121.1 (2)
C15—C16—H16	120.3	C3S—C1S—C2S	117.1 (2)
C16—C17—C12	121.13 (11)	C1S—C2S—H2S1	109.5
C16—C17—H17	119.4	C1S—C2S—H2S2	109.5
C12—C17—H17	119.4	H2S1—C2S—H2S2	109.5
O2—C18—C19	121.20 (11)	C1S—C2S—H2S3	109.5
O2—C18—C9	120.73 (10)	H2S1—C2S—H2S3	109.5
C19—C18—C9	117.99 (10)	H2S2—C2S—H2S3	109.5
C20—C19—C24	118.57 (11)	C1S—C3S—H3S1	109.5
C20—C19—C18	119.23 (11)	H3S1—C3S—H3S2	109.5
C24—C19—C18	122.18 (11)	H3S1—C3S—H3S3	109.5
C21—C20—C19	121.61 (12)	H3S2—C3S—H3S3	109.5
C21—C20—H20	119.2
C25—O3—C2—C1	144.21 (12)	O1—C11—C12—C13	0.48 (16)
C25—O3—C2—C3	−40.90 (17)	C1—C11—C12—C13	179.74 (10)
C10—C1—C2—O3	175.75 (10)	C17—C12—C13—C14	−1.57 (17)
C11—C1—C2—O3	3.16 (15)	C11—C12—C13—C14	176.45 (11)
C10—C1—C2—C3	0.87 (17)	C12—C13—C14—C15	0.49 (18)
C11—C1—C2—C3	−171.72 (11)	C27—O5—C15—C16	−22.73 (18)
O3—C2—C3—C4	−173.61 (11)	C27—O5—C15—C14	158.29 (11)
C1—C2—C3—C4	0.97 (18)	C13—C14—C15—O5	−179.49 (11)
C2—C3—C4—C5	−1.43 (19)	C13—C14—C15—C16	1.47 (19)
C3—C4—C5—C6	−179.21 (12)	O5—C15—C16—C17	178.76 (12)
C3—C4—C5—C10	0.05 (19)	C14—C15—C16—C17	−2.30 (19)
C4—C5—C6—C7	177.84 (13)	C15—C16—C17—C12	1.20 (18)
C10—C5—C6—C7	−1.4 (2)	C13—C12—C17—C16	0.71 (17)
C5—C6—C7—C8	−1.3 (2)	C11—C12—C17—C16	−177.22 (11)
C26—O4—C8—C9	−164.56 (14)	C8—C9—C18—O2	−80.03 (15)
C26—O4—C8—C7	14.4 (2)	C10—C9—C18—O2	104.23 (14)
C6—C7—C8—O4	−176.42 (13)	C8—C9—C18—C19	96.73 (13)
C6—C7—C8—C9	2.5 (2)	C10—C9—C18—C19	−79.01 (14)
O4—C8—C9—C10	178.17 (11)	O2—C18—C19—C20	−8.52 (16)
C7—C8—C9—C10	−0.8 (2)	C9—C18—C19—C20	174.74 (10)
O4—C8—C9—C18	2.23 (17)	O2—C18—C19—C24	169.87 (11)
C7—C8—C9—C18	−176.74 (12)	C9—C18—C19—C24	−6.87 (16)
C8—C9—C10—C5	−1.91 (17)	C24—C19—C20—C21	−0.75 (18)
C18—C9—C10—C5	173.65 (11)	C18—C19—C20—C21	177.70 (11)
C8—C9—C10—C1	−179.77 (11)	C19—C20—C21—C22	0.07 (18)
C18—C9—C10—C1	−4.20 (18)	C30—O6—C22—C23	162.23 (12)
C6—C5—C10—C9	3.00 (17)	C30—O6—C22—C21	−18.9 (2)
C4—C5—C10—C9	−176.27 (11)	C20—C21—C22—O6	−178.25 (12)
C6—C5—C10—C1	−178.99 (11)	C20—C21—C22—C23	0.59 (19)
C4—C5—C10—C1	1.75 (16)	O6—C22—C23—C24	178.38 (12)
C2—C1—C10—C9	175.67 (11)	C21—C22—C23—C24	−0.6 (2)
C11—C1—C10—C9	−12.26 (17)	C22—C23—C24—C19	−0.13 (19)
C2—C1—C10—C5	−2.18 (16)	C20—C19—C24—C23	0.77 (18)
C11—C1—C10—C5	169.88 (10)	C18—C19—C24—C23	−177.63 (11)
C2—C1—C11—O1	107.36 (12)	C15—O5—C27—C28	−59.83 (15)
C10—C1—C11—O1	−64.98 (14)	O5—C27—C28—C29	−49.10 (15)
C2—C1—C11—C12	−71.92 (13)	C27—C28—C29—C30	178.19 (11)
C10—C1—C11—C12	115.74 (12)	C22—O6—C30—C29	−65.93 (17)
O1—C11—C12—C17	178.41 (11)	C28—C29—C30—O6	−45.27 (16)
C1—C11—C12—C17	−2.33 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.47	3.3241 (15)	150
C6—H6···O1ii	0.95	2.38	3.3245 (16)	172
C7—H7···O3ii	0.95	2.59	3.3910 (17)	143
C14—H14···O5iii	0.95	2.40	3.3328 (15)	169
C21—H21···O1Siv	0.95	2.54	3.482 (2)	172
C2S—H2S2···Cgv	0.98	2.86	3.830 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.47	3.3241 (15)	150
C6—H6⋯O1ii	0.95	2.38	3.3245 (16)	172
C7—H7⋯O3ii	0.95	2.59	3.3910 (17)	143
C14—H14⋯O5iii	0.95	2.40	3.3328 (15)	169
C21—H21⋯O1S iv	0.95	2.54	3.482 (2)	172
C2S—H2S2⋯Cg v	0.98	2.86	3.830 (2)	171

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .