6-[(2E)-3,7-Dimethyl-octa-2,6-dien-1-yl]-5,7-dihy-droxy-8-(2-methyl-butano-yl)-4-phenyl-2H-chromen-2-one-6-[(2E)-3,7-dimethyl-octa-2,6-dien-1-yl]-5,7-dihy-droxy-8-(3-methyl-butano-yl)-4-phenyl-2H-chromen-2-one (1/1) from Mesua elegans.

The title co-crystal, C(30)H(34)O(5)·C(30)H(34)O(5), comprises a 1:1 mixture of two mostly superimposed mol-ecules with the same chemical formula that differ in the nature of the substituent (2-methyl-butanoyl or 3-methyl-butano-yl) bound at the exocyclic ketone. The lactone ring is close to planar (r.m.s. deviation = 0.058 Å) and the phenyl ring is twisted out of this plane [dihedral angle = 60.08 (9)°]. The geranyl substituent is almost normal to benzene ring to which it is connected [C-C-C(ar)-C(ar) (ar = aromatic) torsion angle = -87.8 (2)°]. Intra-molecular O-H⋯O and O-H⋯π inter-actions are formed. In the crystal, supra-molecular chains are formed along the a axis owing to C-H⋯O contacts, with the lactone carbonyl atom accepting two such bonds.

Related literature

For the spectroscopic characterization of the title material, see: Verotta et al. (2004 ▶) and for its acetyl­cholinesterase (AChE) inhibitory properties, see: Awang et al. (2010 ▶).

Experimental

Crystal data

C30H34O5·C30H34O5

M = 949.14

Triclinic,

a = 5.9426 (2) Å

b = 13.4688 (5) Å

c = 16.3275 (6) Å

α = 91.955 (3)°

β = 99.515 (3)°

γ = 95.834 (3)°

V = 1280.47 (8) Å3

Z = 1

Cu Kα radiation

μ = 0.66 mm−1

T = 100 K

0.30 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.826, T max = 0.968

25960 measured reflections

5330 independent reflections

4528 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.208

S = 1.01

5330 reflections

363 parameters

54 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.53 e Å−3

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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008628/hb6652sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008628/hb6652Isup2.hkl

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

C30H34O5·C30H34O5	Z = 1
Mr = 949.14	F(000) = 508
Triclinic, P1	Dx = 1.231 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.9426 (2) Å	Cell parameters from 8956 reflections
b = 13.4688 (5) Å	θ = 2.8–76.3°
c = 16.3275 (6) Å	µ = 0.66 mm−1
α = 91.955 (3)°	T = 100 K
β = 99.515 (3)°	Prism, colourless
γ = 95.834 (3)°	0.30 × 0.15 × 0.05 mm
V = 1280.47 (8) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	5330 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4528 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.045
Detector resolution: 10.4041 pixels mm-1	θmax = 76.5°, θmin = 2.8°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
Tmin = 0.826, Tmax = 0.968	l = −20→20
25960 measured reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.1357P)2 + 0.5208P] where P = (Fo2 + 2Fc2)/3
5330 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.57 e Å−3
54 restraints	Δρmin = −0.53 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.9303 (2)	0.47777 (9)	0.36863 (8)	0.0331 (3)
O2	1.2727 (2)	0.55978 (10)	0.41312 (9)	0.0390 (3)
O3	0.7244 (2)	0.13093 (9)	0.41205 (9)	0.0399 (4)
H3o	0.851 (3)	0.138 (2)	0.4450 (14)	0.052 (7)*
O4	0.1977 (2)	0.30693 (11)	0.25255 (9)	0.0415 (4)
H4o	0.198 (6)	0.3641 (14)	0.232 (2)	0.080 (10)*
O5	0.284 (4)	0.473 (2)	0.218 (3)	0.046 (2)	0.50
O5'	0.308 (4)	0.489 (2)	0.223 (3)	0.046 (2)	0.50
C1	1.1476 (3)	0.48355 (13)	0.41647 (12)	0.0329 (4)
C2	1.1949 (3)	0.40121 (13)	0.46801 (11)	0.0325 (4)
H2	1.3363	0.4046	0.5055	0.039*
C3	1.0417 (3)	0.31880 (13)	0.46420 (11)	0.0311 (4)
C4	0.8304 (3)	0.30996 (13)	0.40438 (11)	0.0308 (4)
C5	0.6749 (3)	0.22155 (13)	0.38407 (11)	0.0326 (4)
C6	0.4647 (3)	0.22110 (13)	0.33394 (11)	0.0340 (4)
C7	0.4069 (3)	0.31019 (14)	0.29808 (11)	0.0344 (4)
C8	0.5641 (3)	0.39885 (14)	0.30749 (11)	0.0344 (4)
C9	0.7747 (3)	0.39437 (13)	0.36031 (11)	0.0314 (4)
C10	1.0886 (3)	0.24091 (13)	0.52593 (11)	0.0330 (4)
C11	1.2800 (4)	0.18927 (16)	0.52804 (13)	0.0422 (5)
H11	1.3861	0.2055	0.4917	0.051*
C12	1.3170 (4)	0.11372 (18)	0.58338 (15)	0.0508 (6)
H12	1.4461	0.0774	0.5836	0.061*
C13	1.1665 (4)	0.09147 (16)	0.63781 (14)	0.0475 (5)
H13	1.1912	0.0395	0.6751	0.057*
C14	0.9803 (4)	0.14473 (15)	0.63803 (13)	0.0439 (5)
H14	0.8794	0.1305	0.6766	0.053*
C15	0.9392 (4)	0.21920 (14)	0.58222 (13)	0.0390 (4)
H15	0.8098	0.2552	0.5824	0.047*
C16	0.3045 (3)	0.12556 (14)	0.31303 (12)	0.0372 (4)
H16A	0.3228	0.0817	0.3606	0.045*
H16B	0.1435	0.1414	0.3026	0.045*
C17	0.3576 (3)	0.07200 (14)	0.23678 (13)	0.0377 (4)
H17	0.5157	0.0679	0.2355	0.045*
C18	0.2122 (3)	0.03001 (13)	0.17137 (12)	0.0336 (4)
C19	−0.0431 (3)	0.02650 (17)	0.16256 (13)	0.0427 (5)
H19A	−0.0823	0.0682	0.2074	0.064*
H19B	−0.1095	−0.0426	0.1658	0.064*
H19C	−0.1049	0.0516	0.1087	0.064*
C20	0.2995 (3)	−0.01785 (14)	0.09938 (12)	0.0378 (4)
H20A	0.4624	0.0082	0.1015	0.045*
H20B	0.2117	0.0022	0.0468	0.045*
C21	0.2809 (5)	−0.13182 (16)	0.09853 (15)	0.0547 (6)
H21A	0.3737	−0.1526	0.1499	0.066*
H21B	0.1191	−0.1584	0.0979	0.066*
C22	0.3627 (5)	−0.17516 (16)	0.02434 (15)	0.0501 (5)
H22	0.5179	−0.1552	0.0197	0.060*
C23	0.2449 (4)	−0.23810 (17)	−0.03575 (14)	0.0501 (5)
C24	0.3472 (5)	−0.27142 (19)	−0.10876 (16)	0.0590 (6)
H24A	0.5074	−0.2421	−0.1023	0.089*
H24B	0.2603	−0.2494	−0.1600	0.089*
H24C	0.3409	−0.3445	−0.1116	0.089*
C25	0.0024 (6)	−0.2785 (4)	−0.0393 (2)	0.0989 (14)
H25A	−0.0533	−0.2536	0.0100	0.148*
H25B	−0.0096	−0.3517	−0.0407	0.148*
H25C	−0.0907	−0.2570	−0.0895	0.148*
C26	0.480 (2)	0.4832 (7)	0.2594 (10)	0.0424 (9)	0.50
C27	0.6207 (16)	0.5821 (7)	0.2569 (5)	0.0590 (13)	0.50
H27	0.7212	0.5942	0.3125	0.071*	0.50
C26'	0.506 (2)	0.4880 (7)	0.2608 (9)	0.0424 (9)	0.50
C27'	0.6741 (18)	0.5785 (8)	0.2554 (6)	0.0590 (13)	0.50
H27A	0.8304	0.5578	0.2586	0.071*	0.50
H27B	0.6755	0.6263	0.3029	0.071*	0.50
C28	0.7818 (6)	0.5736 (2)	0.1937 (2)	0.0311 (7)	0.50
H28A	0.8578	0.5118	0.2025	0.037*	0.50
H28B	0.6900	0.5676	0.1370	0.037*	0.50
C29	0.9641 (7)	0.6620 (3)	0.1995 (3)	0.0458 (9)	0.50
H29A	1.0600	0.6530	0.1570	0.069*	0.50
H29B	1.0598	0.6668	0.2547	0.069*	0.50
H29C	0.8902	0.7235	0.1905	0.069*	0.50
C30	0.4816 (13)	0.6723 (6)	0.2447 (5)	0.117 (3)	0.50
H30A	0.3892	0.6764	0.2889	0.176*	0.50
H30B	0.3803	0.6642	0.1905	0.176*	0.50
H30C	0.5868	0.7336	0.2469	0.176*	0.50
C28'	0.6076 (11)	0.6297 (4)	0.1732 (3)	0.0737 (16)	0.50
H28'	0.4480	0.6489	0.1690	0.088*	0.50
C29'	0.7783 (13)	0.7238 (4)	0.1787 (4)	0.089 (2)	0.50
H29D	0.7365	0.7635	0.1304	0.133*	0.50
H29E	0.9333	0.7046	0.1794	0.133*	0.50
H29F	0.7744	0.7635	0.2298	0.133*	0.50
C30'	0.6254 (7)	0.5651 (3)	0.0980 (2)	0.0362 (8)	0.50
H30D	0.5155	0.5051	0.0944	0.054*	0.50
H30E	0.7814	0.5457	0.1029	0.054*	0.50
H30F	0.5910	0.6025	0.0479	0.054*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0368 (7)	0.0244 (6)	0.0359 (7)	−0.0024 (5)	0.0040 (5)	−0.0023 (5)
O2	0.0393 (7)	0.0253 (6)	0.0494 (8)	−0.0036 (5)	0.0038 (6)	−0.0011 (5)
O3	0.0433 (8)	0.0231 (6)	0.0500 (8)	−0.0009 (5)	0.0025 (6)	−0.0037 (5)
O4	0.0383 (7)	0.0393 (8)	0.0431 (8)	−0.0025 (6)	0.0004 (6)	−0.0012 (6)
O5	0.049 (4)	0.029 (7)	0.051 (4)	−0.010 (4)	−0.012 (3)	0.001 (6)
O5'	0.049 (4)	0.029 (7)	0.051 (4)	−0.010 (4)	−0.012 (3)	0.001 (6)
C1	0.0351 (9)	0.0258 (8)	0.0366 (9)	−0.0003 (7)	0.0062 (7)	−0.0049 (7)
C2	0.0335 (9)	0.0274 (9)	0.0351 (9)	−0.0004 (7)	0.0045 (7)	−0.0024 (7)
C3	0.0353 (9)	0.0255 (8)	0.0329 (9)	0.0016 (7)	0.0089 (7)	−0.0044 (6)
C4	0.0338 (9)	0.0259 (8)	0.0323 (8)	−0.0013 (7)	0.0084 (7)	−0.0039 (6)
C5	0.0381 (9)	0.0248 (8)	0.0351 (9)	0.0001 (7)	0.0098 (7)	−0.0042 (7)
C6	0.0366 (9)	0.0285 (9)	0.0359 (9)	−0.0041 (7)	0.0089 (7)	−0.0066 (7)
C7	0.0364 (9)	0.0337 (9)	0.0317 (9)	−0.0013 (7)	0.0061 (7)	−0.0055 (7)
C8	0.0406 (10)	0.0302 (9)	0.0306 (8)	−0.0019 (7)	0.0056 (7)	−0.0032 (7)
C9	0.0355 (9)	0.0263 (8)	0.0315 (8)	−0.0027 (7)	0.0083 (7)	−0.0054 (6)
C10	0.0386 (9)	0.0248 (8)	0.0338 (9)	−0.0015 (7)	0.0052 (7)	−0.0029 (7)
C11	0.0449 (11)	0.0420 (11)	0.0431 (11)	0.0092 (9)	0.0131 (9)	0.0075 (8)
C12	0.0566 (13)	0.0470 (12)	0.0535 (13)	0.0172 (10)	0.0144 (10)	0.0115 (10)
C13	0.0650 (14)	0.0336 (10)	0.0455 (11)	0.0064 (9)	0.0128 (10)	0.0069 (8)
C14	0.0588 (13)	0.0320 (10)	0.0441 (11)	0.0018 (9)	0.0198 (9)	0.0035 (8)
C15	0.0453 (11)	0.0293 (9)	0.0441 (10)	0.0029 (8)	0.0137 (8)	−0.0001 (7)
C16	0.0371 (9)	0.0306 (9)	0.0415 (10)	−0.0047 (7)	0.0067 (8)	−0.0072 (7)
C17	0.0322 (9)	0.0322 (9)	0.0470 (11)	0.0008 (7)	0.0055 (8)	−0.0077 (8)
C18	0.0356 (9)	0.0264 (8)	0.0379 (9)	−0.0008 (7)	0.0060 (7)	−0.0002 (7)
C19	0.0368 (10)	0.0494 (12)	0.0400 (10)	−0.0012 (8)	0.0056 (8)	−0.0044 (8)
C20	0.0386 (10)	0.0322 (9)	0.0409 (10)	−0.0008 (7)	0.0064 (8)	−0.0050 (7)
C21	0.0848 (18)	0.0338 (11)	0.0472 (12)	0.0082 (11)	0.0157 (12)	−0.0017 (9)
C22	0.0640 (14)	0.0358 (11)	0.0521 (13)	0.0076 (10)	0.0146 (11)	−0.0051 (9)
C23	0.0633 (14)	0.0430 (11)	0.0439 (11)	0.0074 (10)	0.0083 (10)	−0.0009 (9)
C24	0.0779 (17)	0.0476 (13)	0.0526 (13)	0.0122 (12)	0.0136 (12)	−0.0113 (10)
C25	0.084 (2)	0.146 (4)	0.0572 (17)	−0.037 (2)	0.0231 (16)	−0.030 (2)
C26	0.048 (3)	0.0361 (12)	0.0364 (11)	−0.0067 (14)	−0.0059 (15)	0.0013 (10)
C27	0.051 (4)	0.0474 (15)	0.0629 (16)	−0.020 (2)	−0.0257 (19)	0.0194 (12)
C26'	0.048 (3)	0.0361 (12)	0.0364 (11)	−0.0067 (14)	−0.0059 (15)	0.0013 (10)
C27'	0.051 (4)	0.0474 (15)	0.0629 (16)	−0.020 (2)	−0.0257 (19)	0.0194 (12)
C28	0.0366 (17)	0.0258 (16)	0.0301 (16)	0.0024 (13)	0.0019 (13)	0.0110 (12)
C29	0.050 (2)	0.0336 (19)	0.054 (2)	−0.0012 (17)	0.0135 (19)	0.0053 (17)
C30	0.115 (6)	0.101 (5)	0.114 (6)	−0.012 (5)	−0.033 (5)	0.032 (5)
C28'	0.078 (4)	0.064 (3)	0.073 (4)	−0.001 (3)	−0.001 (3)	0.005 (3)
C29'	0.101 (5)	0.068 (4)	0.089 (4)	−0.005 (3)	−0.004 (4)	0.017 (3)
C30'	0.051 (2)	0.0264 (16)	0.0316 (17)	−0.0002 (15)	0.0093 (15)	0.0057 (13)

O1—C9	1.368 (2)	C19—H19C	0.9800
O1—C1	1.388 (2)	C20—C21	1.527 (3)
O2—C1	1.213 (2)	C20—H20A	0.9900
O3—C5	1.361 (2)	C20—H20B	0.9900
O3—H3o	0.844 (10)	C21—C22	1.499 (3)
O4—C7	1.335 (2)	C21—H21A	0.9900
O4—H4o	0.853 (10)	C21—H21B	0.9900
O5—C26	1.240 (6)	C22—C23	1.329 (3)
O5'—C26'	1.238 (6)	C22—H22	0.9500
C1—C2	1.437 (3)	C23—C25	1.479 (4)
C2—C3	1.355 (2)	C23—C24	1.500 (3)
C2—H2	0.9500	C24—H24A	0.9800
C3—C4	1.450 (3)	C24—H24B	0.9800
C3—C10	1.494 (2)	C24—H24C	0.9800
C4—C9	1.405 (3)	C25—H25A	0.9800
C4—C5	1.425 (2)	C25—H25B	0.9800
C5—C6	1.375 (3)	C25—H25C	0.9800
C6—C7	1.402 (3)	C26—C27	1.504 (6)
C6—C16	1.514 (2)	C27—C28	1.528 (4)
C7—C8	1.427 (3)	C27—C30	1.538 (5)
C8—C9	1.405 (3)	C27—H27	1.0000
C8—C26	1.483 (6)	C26'—C27'	1.510 (6)
C8—C26'	1.484 (6)	C27'—C28'	1.541 (11)
C10—C11	1.389 (3)	C27'—H27A	0.9900
C10—C15	1.398 (3)	C27'—H27B	0.9900
C11—C12	1.394 (3)	C28—C29	1.516 (4)
C11—H11	0.9500	C28—H28A	0.9900
C12—C13	1.380 (3)	C28—H28B	0.9900
C12—H12	0.9500	C29—H29A	0.9800
C13—C14	1.379 (3)	C29—H29B	0.9800
C13—H13	0.9500	C29—H29C	0.9800
C14—C15	1.391 (3)	C30—H30A	0.9800
C14—H14	0.9500	C30—H30B	0.9800
C15—H15	0.9500	C30—H30C	0.9800
C16—C17	1.511 (3)	C28'—C30'	1.505 (4)
C16—H16A	0.9900	C28'—C29'	1.531 (4)
C16—H16B	0.9900	C28'—H28'	1.0000
C17—C18	1.327 (3)	C29'—H29D	0.9800
C17—H17	0.9500	C29'—H29E	0.9800
C18—C19	1.496 (3)	C29'—H29F	0.9800
C18—C20	1.511 (3)	C30'—H30D	0.9800
C19—H19A	0.9800	C30'—H30E	0.9800
C19—H19B	0.9800	C30'—H30F	0.9800
C9—O1—C1	123.73 (14)	C20—C21—H21A	109.3
C5—O3—H3o	108.8 (19)	C22—C21—H21B	109.3
C7—O4—H4o	103 (2)	C20—C21—H21B	109.3
O2—C1—O1	116.26 (17)	H21A—C21—H21B	108.0
O2—C1—C2	127.17 (18)	C23—C22—C21	128.0 (2)
O1—C1—C2	116.46 (15)	C23—C22—H22	116.0
C3—C2—C1	121.27 (17)	C21—C22—H22	116.0
C3—C2—H2	119.4	C22—C23—C25	124.1 (2)
C1—C2—H2	119.4	C22—C23—C24	122.0 (2)
C2—C3—C4	120.15 (17)	C25—C23—C24	113.8 (2)
C2—C3—C10	118.72 (17)	C23—C24—H24A	109.5
C4—C3—C10	121.03 (15)	C23—C24—H24B	109.5
C9—C4—C5	116.29 (17)	H24A—C24—H24B	109.5
C9—C4—C3	118.02 (16)	C23—C24—H24C	109.5
C5—C4—C3	125.66 (17)	H24A—C24—H24C	109.5
O3—C5—C6	114.94 (16)	H24B—C24—H24C	109.5
O3—C5—C4	122.49 (17)	C23—C25—H25A	109.5
C6—C5—C4	122.57 (17)	C23—C25—H25B	109.5
C5—C6—C7	118.48 (16)	H25A—C25—H25B	109.5
C5—C6—C16	121.17 (17)	C23—C25—H25C	109.5
C7—C6—C16	120.24 (17)	H25A—C25—H25C	109.5
O4—C7—C6	116.21 (16)	H25B—C25—H25C	109.5
O4—C7—C8	121.54 (17)	O5—C26—C8	119.2 (19)
C6—C7—C8	122.22 (17)	O5—C26—C27	116.9 (16)
C9—C8—C7	116.14 (17)	C8—C26—C27	123.9 (8)
C9—C8—C26	129.2 (6)	C26—C27—C28	109.4 (9)
C7—C8—C26	114.7 (6)	C26—C27—C30	115.0 (7)
C9—C8—C26'	123.4 (6)	C28—C27—C30	113.0 (5)
C7—C8—C26'	120.5 (6)	C26—C27—H27	106.2
O1—C9—C8	117.12 (16)	C28—C27—H27	106.2
O1—C9—C4	119.40 (16)	C30—C27—H27	106.2
C8—C9—C4	123.48 (16)	O5'—C26'—C8	118.4 (19)
C11—C10—C15	119.28 (18)	O5'—C26'—C27'	117.3 (17)
C11—C10—C3	120.61 (17)	C8—C26'—C27'	124.3 (9)
C15—C10—C3	120.11 (17)	C26'—C27'—C28'	110.6 (7)
C10—C11—C12	120.20 (19)	C26'—C27'—H27A	109.5
C10—C11—H11	119.9	C28'—C27'—H27A	109.5
C12—C11—H11	119.9	C26'—C27'—H27B	109.5
C13—C12—C11	120.2 (2)	C28'—C27'—H27B	109.5
C13—C12—H12	119.9	H27A—C27'—H27B	108.1
C11—C12—H12	119.9	C29—C28—C27	113.2 (5)
C14—C13—C12	120.0 (2)	C29—C28—H28A	108.9
C14—C13—H13	120.0	C27—C28—H28A	108.9
C12—C13—H13	120.0	C29—C28—H28B	108.9
C13—C14—C15	120.48 (19)	C27—C28—H28B	108.9
C13—C14—H14	119.8	H28A—C28—H28B	107.8
C15—C14—H14	119.8	C28—C29—H29A	109.5
C14—C15—C10	119.84 (19)	C28—C29—H29B	109.5
C14—C15—H15	120.1	H29A—C29—H29B	109.5
C10—C15—H15	120.1	C28—C29—H29C	109.5
C17—C16—C6	110.01 (16)	H29A—C29—H29C	109.5
C17—C16—H16A	109.7	H29B—C29—H29C	109.5
C6—C16—H16A	109.7	C27—C30—H30A	109.5
C17—C16—H16B	109.7	C27—C30—H30B	109.5
C6—C16—H16B	109.7	H30A—C30—H30B	109.5
H16A—C16—H16B	108.2	C27—C30—H30C	109.5
C18—C17—C16	128.44 (18)	H30A—C30—H30C	109.5
C18—C17—H17	115.8	H30B—C30—H30C	109.5
C16—C17—H17	115.8	C30'—C28'—C29'	109.5 (4)
C17—C18—C19	123.89 (18)	C30'—C28'—C27'	112.7 (6)
C17—C18—C20	120.64 (18)	C29'—C28'—C27'	105.2 (7)
C19—C18—C20	115.46 (16)	C30'—C28'—H28'	109.8
C18—C19—H19A	109.5	C29'—C28'—H28'	109.8
C18—C19—H19B	109.5	C27'—C28'—H28'	109.8
H19A—C19—H19B	109.5	C28'—C29'—H29D	109.5
C18—C19—H19C	109.5	C28'—C29'—H29E	109.5
H19A—C19—H19C	109.5	H29D—C29'—H29E	109.5
H19B—C19—H19C	109.5	C28'—C29'—H29F	109.5
C18—C20—C21	114.04 (17)	H29D—C29'—H29F	109.5
C18—C20—H20A	108.7	H29E—C29'—H29F	109.5
C21—C20—H20A	108.7	C28'—C30'—H30D	109.5
C18—C20—H20B	108.7	C28'—C30'—H30E	109.5
C21—C20—H20B	108.7	H30D—C30'—H30E	109.5
H20A—C20—H20B	107.6	C28'—C30'—H30F	109.5
C22—C21—C20	111.63 (19)	H30D—C30'—H30F	109.5
C22—C21—H21A	109.3	H30E—C30'—H30F	109.5
C9—O1—C1—O2	174.82 (16)	C4—C3—C10—C15	−59.2 (2)
C9—O1—C1—C2	−8.6 (2)	C15—C10—C11—C12	2.7 (3)
O2—C1—C2—C3	−178.28 (18)	C3—C10—C11—C12	−177.2 (2)
O1—C1—C2—C3	5.6 (3)	C10—C11—C12—C13	−1.6 (4)
C1—C2—C3—C4	3.2 (3)	C11—C12—C13—C14	−0.6 (4)
C1—C2—C3—C10	−173.11 (16)	C12—C13—C14—C15	1.7 (3)
C2—C3—C4—C9	−9.5 (3)	C13—C14—C15—C10	−0.6 (3)
C10—C3—C4—C9	166.80 (16)	C11—C10—C15—C14	−1.6 (3)
C2—C3—C4—C5	168.59 (17)	C3—C10—C15—C14	178.26 (18)
C10—C3—C4—C5	−15.1 (3)	C5—C6—C16—C17	−87.8 (2)
C9—C4—C5—O3	169.56 (16)	C7—C6—C16—C17	88.2 (2)
C3—C4—C5—O3	−8.5 (3)	C6—C16—C17—C18	−135.2 (2)
C9—C4—C5—C6	−9.6 (3)	C16—C17—C18—C19	−1.5 (3)
C3—C4—C5—C6	172.29 (17)	C16—C17—C18—C20	178.18 (18)
O3—C5—C6—C7	−175.86 (16)	C17—C18—C20—C21	102.3 (2)
C4—C5—C6—C7	3.4 (3)	C19—C18—C20—C21	−78.0 (2)
O3—C5—C6—C16	0.2 (3)	C18—C20—C21—C22	178.11 (19)
C4—C5—C6—C16	179.46 (16)	C20—C21—C22—C23	−119.9 (3)
C5—C6—C7—O4	−177.50 (16)	C21—C22—C23—C25	−0.6 (5)
C16—C6—C7—O4	6.4 (3)	C21—C22—C23—C24	177.0 (2)
C5—C6—C7—C8	4.2 (3)	C9—C8—C26—O5	−177.9 (19)
C16—C6—C7—C8	−171.91 (17)	C7—C8—C26—O5	2.2 (10)
O4—C7—C8—C9	176.91 (16)	C26'—C8—C26—O5	165 (12)
C6—C7—C8—C9	−4.9 (3)	C9—C8—C26—C27	2.8 (19)
O4—C7—C8—C26	−3.1 (8)	C7—C8—C26—C27	−177.2 (10)
C6—C7—C8—C26	175.1 (8)	C26'—C8—C26—C27	−14 (12)
O4—C7—C8—C26'	−5.2 (8)	O5—C26—C27—C28	−97.7 (14)
C6—C7—C8—C26'	173.0 (8)	C8—C26—C27—C28	81.7 (14)
C1—O1—C9—C8	−177.96 (15)	O5—C26—C27—C30	30.8 (11)
C1—O1—C9—C4	2.4 (2)	C8—C26—C27—C30	−149.8 (11)
C7—C8—C9—O1	178.44 (15)	C9—C8—C26'—O5'	−172.3 (17)
C26—C8—C9—O1	−1.5 (9)	C7—C8—C26'—O5'	9.9 (9)
C26'—C8—C9—O1	0.6 (9)	C26—C8—C26'—O5'	−8 (14)
C7—C8—C9—C4	−2.0 (3)	C9—C8—C26'—C27'	8.4 (18)
C26—C8—C9—C4	178.1 (9)	C7—C8—C26'—C27'	−169.4 (9)
C26'—C8—C9—C4	−179.8 (8)	C26—C8—C26'—C27'	173 (14)
C5—C4—C9—O1	−171.55 (15)	O5'—C26'—C27'—C28'	−27.9 (12)
C3—C4—C9—O1	6.7 (2)	C8—C26'—C27'—C28'	151.4 (12)
C5—C4—C9—C8	8.9 (3)	C26—C27—C28—C29	−167.9 (5)
C3—C4—C9—C8	−172.90 (16)	C30—C27—C28—C29	62.5 (9)
C2—C3—C10—C11	−63.0 (2)	C26'—C27'—C28'—C30'	−65.2 (9)
C4—C3—C10—C11	120.7 (2)	C26'—C27'—C28'—C29'	175.6 (8)
C2—C3—C10—C15	117.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···O5	0.85 (1)	1.54 (4)	2.35 (3)	158 (4)
O4—H4o···O5′	0.85 (1)	1.76 (4)	2.55 (3)	154 (3)
O3—H3o···Cg1	0.84 (2)	2.56 (4)	3.355 (2)	158 (4)
C2—H2···O2i	0.95	2.47	3.408 (2)	169
C15—H15···O2ii	0.95	2.59	3.351 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4o⋯O5	0.85 (1)	1.54 (4)	2.35 (3)	158 (4)
O4—H4o⋯O5′	0.85 (1)	1.76 (4)	2.55 (3)	154 (3)
O3—H3o⋯Cg1	0.84 (2)	2.56 (4)	3.355 (2)	158 (4)
C2—H2⋯O2i	0.95	2.47	3.408 (2)	169
C15—H15⋯O2ii	0.95	2.59	3.351 (2)	137

Symmetry codes: (i) ; (ii) .