4-(2,5-Dihexyl-oxyphen-yl)benzoic acid.

In the title compound, C(25)H(34)O(4), one n-hexyl chain of the hex-yloxy group adopts a fully extended all-trans conformation, and the other n-hexyl chain displays disorder with site occupancies of 0.470 (3) and 0.530 (3). The dihedral angle between the benzene rings is 44.5 (3)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds form dimers via crystallographic inversion centres.

Related literature

For a review of applications of Suzuki–Miyura cross-coupling reactions in organic syntheses, see: Kotha et al. (2002 ▶). For the structure of 1,4-dibromo-2,5-bis­(hex­yloxy)benzene, see: Li et al. (2008 ▶). For the syntheses of related compounds, see: Maruyama & Kawanishi (2002 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

C25H34O4

M = 398.52

Monoclinic,

a = 7.2936 (12) Å

b = 14.689 (2) Å

c = 22.137 (4) Å

β = 95.283 (3)°

V = 2361.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 (2) K

0.35 × 0.15 × 0.06 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.996

15777 measured reflections

4359 independent reflections

1432 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.194

S = 0.97

4359 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 global, I. DOI: 10.1107/S1600536808032170/si2116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032170/si2116Isup2.hkl

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

C25H34O4	F(000) = 864
Mr = 398.52	Dx = 1.121 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.2936 (12) Å	Cell parameters from 918 reflections
b = 14.689 (2) Å	θ = 2.8–17.8°
c = 22.137 (4) Å	µ = 0.07 mm−1
β = 95.283 (3)°	T = 295 K
V = 2361.7 (7) Å3	Block, colourless
Z = 4	0.35 × 0.15 × 0.06 mm

Bruker SMART CCD diffractometer	4359 independent reflections
Radiation source: fine-focus sealed tube	1432 reflections with I > 2σ(I)
graphite	Rint = 0.087
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.975, Tmax = 0.996	k = −17→17
15777 measured reflections	l = −26→26

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)] = 0.061	H-atom parameters constrained
wR(F2) = 0.194	w = 1/[σ2(Fo2) + (0.0705P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
4359 reflections	Δρmax = 0.16 e Å−3
257 parameters	Δρmin = −0.14 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: 0.0061 (13)

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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	Occ. (<1)
C20	0.7088 (7)	0.0256 (3)	0.2574 (2)	0.1007 (16)	0.470 (3)
H20A	0.7986	−0.0208	0.2703	0.121*	0.470 (3)
H20B	0.6837	0.0216	0.2136	0.121*	0.470 (3)
C21	0.5320 (5)	0.0098 (4)	0.28753 (19)	0.108 (3)	0.470 (3)
H21A	0.4350	0.0476	0.2679	0.129*	0.470 (3)
H21B	0.4949	−0.0533	0.2821	0.129*	0.470 (3)
C22	0.5551 (5)	0.0315 (5)	0.35456 (16)	0.137 (4)	0.470 (3)
H22A	0.5929	0.0946	0.3594	0.165*	0.470 (3)
H22B	0.6542	−0.0058	0.3734	0.165*	0.470 (3)
C23	0.3866 (6)	0.0171 (4)	0.3885 (2)	0.155 (4)	0.470 (3)
H23A	0.3371	−0.0429	0.3787	0.187*	0.470 (3)
H23B	0.4241	0.0183	0.4317	0.187*	0.470 (3)
C24	0.2371 (8)	0.0856 (3)	0.3751 (2)	0.162 (3)	0.470 (3)
H24A	0.1901	0.0795	0.3328	0.195*	0.470 (3)
H24B	0.2902	0.1460	0.3803	0.195*	0.470 (3)
C25	0.0785 (8)	0.0786 (4)	0.4134 (2)	0.153 (3)	0.470 (3)
H25A	−0.0192	0.0445	0.3920	0.229*	0.470 (3)
H25B	0.0353	0.1386	0.4219	0.229*	0.470 (3)
H25C	0.1180	0.0483	0.4508	0.229*	0.470 (3)
C20'	0.7495 (6)	0.0177 (3)	0.2742 (2)	0.1007 (16)	0.530 (3)
H20C	0.8659	−0.0135	0.2835	0.121*	0.530 (3)
H20D	0.6987	−0.0016	0.2342	0.121*	0.530 (3)
C21'	0.6199 (6)	−0.0085 (3)	0.3200 (2)	0.108 (3)	0.530 (3)
H21C	0.5838	−0.0714	0.3129	0.129*	0.530 (3)
H21D	0.6861	−0.0053	0.3600	0.129*	0.530 (3)
C22'	0.4489 (5)	0.0478 (2)	0.32045 (16)	0.137 (4)	0.530 (3)
H22C	0.4839	0.1083	0.3347	0.165*	0.530 (3)
H22D	0.3942	0.0537	0.2790	0.165*	0.530 (3)
C23'	0.3055 (5)	0.0122 (3)	0.3584 (2)	0.155 (4)	0.530 (3)
H23C	0.1984	−0.0048	0.3315	0.187*	0.530 (3)
H23D	0.3527	−0.0427	0.3785	0.187*	0.530 (3)
C24'	0.2443 (6)	0.0752 (3)	0.4053 (2)	0.162 (3)	0.530 (3)
H24C	0.2090	0.1325	0.3858	0.195*	0.530 (3)
H24D	0.3487	0.0873	0.4346	0.195*	0.530 (3)
C25'	0.0875 (7)	0.0431 (4)	0.4391 (3)	0.153 (3)	0.530 (3)
H25D	0.0275	−0.0073	0.4180	0.229*	0.530 (3)
H25E	0.0009	0.0918	0.4419	0.229*	0.530 (3)
H25F	0.1336	0.0242	0.4792	0.229*	0.530 (3)
O1	0.7303 (4)	0.4749 (2)	0.48474 (13)	0.1015 (9)
H1	0.6643	0.4951	0.5097	0.152*
O2	0.4582 (4)	0.45546 (17)	0.43055 (11)	0.0937 (9)
O3	1.3854 (4)	0.25963 (18)	0.17662 (11)	0.0957 (9)
O4	0.7809 (4)	0.11432 (17)	0.27390 (12)	0.1056 (10)
C1	0.6290 (7)	0.4451 (3)	0.43801 (19)	0.0811 (12)
C2	0.7271 (6)	0.3934 (2)	0.39327 (17)	0.0735 (10)
C3	0.6246 (5)	0.3488 (3)	0.34666 (18)	0.0766 (11)
H3	0.4969	0.3535	0.3432	0.092*
C4	0.7099 (6)	0.2974 (2)	0.30537 (16)	0.0774 (11)
H4	0.6384	0.2684	0.2741	0.093*
C5	0.9002 (6)	0.2878 (2)	0.30924 (16)	0.0692 (10)
C6	1.0009 (5)	0.3342 (3)	0.35605 (18)	0.0835 (12)
H6	1.1287	0.3303	0.3593	0.100*
C7	0.9163 (6)	0.3863 (3)	0.39816 (17)	0.0832 (11)
H7	0.9869	0.4160	0.4293	0.100*
C8	0.9934 (5)	0.2331 (3)	0.26465 (15)	0.0720 (10)
C9	0.9291 (6)	0.1468 (3)	0.24652 (17)	0.0810 (11)
C10	1.0170 (6)	0.0979 (3)	0.20426 (17)	0.0909 (12)
H10	0.9734	0.0406	0.1923	0.109*
C11	1.1685 (6)	0.1332 (3)	0.17971 (17)	0.0892 (12)
H11	1.2252	0.1001	0.1509	0.107*
C12	1.2361 (6)	0.2173 (3)	0.19762 (17)	0.0791 (11)
C13	1.1469 (5)	0.2661 (3)	0.23992 (15)	0.0761 (11)
H13	1.1922	0.3231	0.2520	0.091*
C14	1.4854 (6)	0.2112 (3)	0.13414 (17)	0.0936 (12)
H14A	1.4047	0.1959	0.0983	0.112*
H14B	1.5351	0.1552	0.1522	0.112*
C15	1.6382 (5)	0.2718 (3)	0.11761 (17)	0.0939 (12)
H15A	1.7197	0.2842	0.1538	0.113*
H15B	1.5863	0.3293	0.1029	0.113*
C16	1.7496 (6)	0.2318 (3)	0.06986 (17)	0.1004 (13)
H16A	1.6698	0.2225	0.0328	0.120*
H16B	1.7964	0.1727	0.0835	0.120*
C17	1.9103 (6)	0.2919 (3)	0.05617 (17)	0.0987 (13)
H17A	1.8627	0.3502	0.0413	0.118*
H17B	1.9872	0.3028	0.0936	0.118*
C18	2.0261 (6)	0.2524 (3)	0.01070 (19)	0.1182 (16)
H18A	1.9485	0.2401	−0.0264	0.142*
H18B	2.0757	0.1947	0.0260	0.142*
C19	2.1840 (6)	0.3126 (3)	−0.0042 (2)	0.1344 (18)
H19A	2.1360	0.3676	−0.0230	0.202*
H19B	2.2569	0.2812	−0.0315	0.202*
H19C	2.2591	0.3273	0.0324	0.202*

	U11	U22	U33	U12	U13	U23
C20	0.121 (4)	0.072 (3)	0.111 (4)	−0.021 (3)	0.019 (3)	−0.011 (3)
C21	0.089 (7)	0.075 (4)	0.163 (8)	0.001 (4)	0.031 (6)	−0.007 (5)
C22	0.124 (8)	0.105 (5)	0.191 (10)	0.015 (5)	0.057 (7)	0.039 (6)
C23	0.119 (7)	0.115 (5)	0.241 (10)	0.004 (5)	0.063 (7)	0.002 (6)
C24	0.217 (8)	0.172 (7)	0.096 (7)	0.008 (6)	0.006 (6)	0.023 (6)
C25	0.112 (5)	0.173 (8)	0.175 (8)	0.034 (5)	0.020 (5)	0.026 (7)
C20'	0.121 (4)	0.072 (3)	0.111 (4)	−0.021 (3)	0.019 (3)	−0.011 (3)
C21'	0.089 (7)	0.075 (4)	0.163 (8)	0.001 (4)	0.031 (6)	−0.007 (5)
C22'	0.124 (8)	0.105 (5)	0.191 (10)	0.015 (5)	0.057 (7)	0.039 (6)
C23'	0.119 (7)	0.115 (5)	0.241 (10)	0.004 (5)	0.063 (7)	0.002 (6)
C24'	0.217 (8)	0.172 (7)	0.096 (7)	0.008 (6)	0.006 (6)	0.023 (6)
C25'	0.112 (5)	0.173 (8)	0.175 (8)	0.034 (5)	0.020 (5)	0.026 (7)
O1	0.102 (2)	0.112 (2)	0.094 (2)	−0.0008 (18)	0.0274 (17)	−0.0269 (18)
O2	0.095 (2)	0.103 (2)	0.0856 (19)	0.0112 (18)	0.0216 (17)	−0.0026 (16)
O3	0.099 (2)	0.097 (2)	0.0964 (19)	−0.0086 (17)	0.0363 (17)	−0.0176 (16)
O4	0.120 (2)	0.0675 (18)	0.137 (2)	−0.0163 (17)	0.052 (2)	−0.0183 (17)
C1	0.096 (4)	0.082 (3)	0.069 (3)	−0.008 (3)	0.022 (3)	0.002 (2)
C2	0.084 (3)	0.069 (2)	0.070 (3)	−0.001 (2)	0.023 (2)	−0.003 (2)
C3	0.080 (3)	0.074 (3)	0.077 (3)	0.000 (2)	0.017 (2)	0.003 (2)
C4	0.081 (3)	0.075 (3)	0.078 (3)	−0.007 (2)	0.011 (2)	−0.002 (2)
C5	0.080 (3)	0.057 (2)	0.071 (3)	−0.001 (2)	0.009 (2)	−0.001 (2)
C6	0.070 (3)	0.089 (3)	0.093 (3)	0.001 (2)	0.017 (2)	−0.012 (2)
C7	0.087 (3)	0.087 (3)	0.078 (3)	−0.006 (2)	0.017 (2)	−0.014 (2)
C8	0.083 (3)	0.063 (3)	0.071 (2)	0.004 (2)	0.014 (2)	−0.007 (2)
C9	0.094 (3)	0.068 (3)	0.084 (3)	−0.004 (2)	0.023 (2)	−0.005 (2)
C10	0.120 (4)	0.069 (3)	0.087 (3)	−0.010 (3)	0.024 (3)	−0.014 (2)
C11	0.108 (3)	0.085 (3)	0.078 (3)	−0.001 (3)	0.026 (2)	−0.013 (2)
C12	0.083 (3)	0.077 (3)	0.080 (3)	−0.002 (3)	0.017 (2)	−0.005 (2)
C13	0.084 (3)	0.071 (3)	0.075 (2)	0.002 (2)	0.012 (2)	−0.012 (2)
C14	0.106 (3)	0.093 (3)	0.086 (3)	0.005 (3)	0.031 (3)	−0.012 (2)
C15	0.095 (3)	0.100 (3)	0.089 (3)	0.004 (3)	0.021 (3)	−0.004 (3)
C16	0.099 (3)	0.110 (3)	0.096 (3)	0.002 (3)	0.028 (3)	−0.020 (3)
C17	0.100 (3)	0.104 (3)	0.096 (3)	0.002 (3)	0.031 (3)	−0.016 (2)
C18	0.110 (4)	0.129 (4)	0.121 (4)	0.001 (3)	0.041 (3)	−0.030 (3)
C19	0.117 (4)	0.154 (5)	0.139 (4)	−0.019 (3)	0.049 (3)	−0.025 (3)

C20—O4	1.440 (5)	O3—C14	1.432 (4)
C20—C21	1.5236 (17)	O4—C9	1.372 (4)
C20—H20A	0.9700	C1—C2	1.483 (5)
C20—H20B	0.9700	C2—C7	1.378 (4)
C21—C22	1.5119 (17)	C2—C3	1.383 (4)
C21—H21A	0.9700	C3—C4	1.378 (4)
C21—H21B	0.9700	C3—H3	0.9300
C22—C23	1.5129 (17)	C4—C5	1.390 (4)
C22—H22A	0.9700	C4—H4	0.9300
C22—H22B	0.9700	C5—C6	1.392 (4)
C23—C24	1.4930 (17)	C5—C8	1.486 (4)
C23—H23A	0.9700	C6—C7	1.393 (4)
C23—H23B	0.9700	C6—H6	0.9300
C24—C25	1.4994 (17)	C7—H7	0.9300
C24—H24A	0.9700	C8—C13	1.379 (4)
C24—H24B	0.9700	C8—C9	1.397 (5)
C25—H25A	0.9600	C9—C10	1.383 (5)
C25—H25B	0.9600	C10—C11	1.377 (5)
C25—H25C	0.9600	C10—H10	0.9300
C20'—O4	1.438 (4)	C11—C12	1.374 (5)
C20'—C21'	1.4978 (17)	C11—H11	0.9300
C20'—H20C	0.9700	C12—C13	1.388 (4)
C20'—H20D	0.9700	C13—H13	0.9300
C21'—C22'	1.4966 (17)	C14—C15	1.498 (5)
C21'—H21C	0.9700	C14—H14A	0.9700
C21'—H21D	0.9700	C14—H14B	0.9700
C22'—C23'	1.4938 (17)	C15—C16	1.510 (4)
C22'—H22C	0.9700	C15—H15A	0.9700
C22'—H22D	0.9700	C15—H15B	0.9700
C23'—C24'	1.4906 (17)	C16—C17	1.520 (5)
C23'—H23C	0.9700	C16—H16A	0.9700
C23'—H23D	0.9700	C16—H16B	0.9700
C24'—C25'	1.4994 (17)	C17—C18	1.490 (4)
C24'—H24C	0.9700	C17—H17A	0.9700
C24'—H24D	0.9700	C17—H17B	0.9700
C25'—H25D	0.9600	C18—C19	1.513 (5)
C25'—H25E	0.9600	C18—H18A	0.9700
C25'—H25F	0.9600	C18—H18B	0.9700
O1—C1	1.291 (4)	C19—H19A	0.9600
O1—H1	0.8200	C19—H19B	0.9600
O2—C1	1.251 (4)	C19—H19C	0.9600
O3—C12	1.372 (4)
O4—C20—C21	109.3 (2)	C7—C2—C3	119.4 (4)
O4—C20—H20A	109.8	C7—C2—C1	121.8 (4)
C21—C20—H20A	109.8	C3—C2—C1	118.7 (4)
O4—C20—H20B	109.8	C4—C3—C2	120.6 (4)
C21—C20—H20B	109.8	C4—C3—H3	119.7
H20A—C20—H20B	108.3	C2—C3—H3	119.7
C22—C21—C20	112.1	C3—C4—C5	121.6 (4)
C22—C21—H21A	109.2	C3—C4—H4	119.2
C20—C21—H21A	109.2	C5—C4—H4	119.2
C22—C21—H21B	109.2	C4—C5—C6	116.9 (3)
C20—C21—H21B	109.2	C4—C5—C8	121.9 (4)
H21A—C21—H21B	107.9	C6—C5—C8	121.2 (4)
C21—C22—C23	115.8	C5—C6—C7	122.1 (4)
C21—C22—H22A	108.3	C5—C6—H6	119.0
C23—C22—H22A	108.3	C7—C6—H6	119.0
C21—C22—H22B	108.3	C2—C7—C6	119.4 (4)
C23—C22—H22B	108.3	C2—C7—H7	120.3
H22A—C22—H22B	107.4	C6—C7—H7	120.3
C24—C23—C22	114.8	C13—C8—C9	118.0 (3)
C24—C23—H23A	108.6	C13—C8—C5	120.7 (4)
C22—C23—H23A	108.6	C9—C8—C5	121.3 (4)
C24—C23—H23B	108.6	O4—C9—C10	123.4 (4)
C22—C23—H23B	108.6	O4—C9—C8	116.5 (4)
H23A—C23—H23B	107.5	C10—C9—C8	120.1 (4)
C23—C24—C25	115.4	C11—C10—C9	120.7 (4)
C23—C24—H24A	108.4	C11—C10—H10	119.7
C25—C24—H24A	108.4	C9—C10—H10	119.7
C23—C24—H24B	108.4	C12—C11—C10	120.3 (4)
C25—C24—H24B	108.4	C12—C11—H11	119.9
H24A—C24—H24B	107.5	C10—C11—H11	119.9
O4—C20'—C21'	111.6 (2)	O3—C12—C11	125.8 (4)
O4—C20'—H20C	109.3	O3—C12—C13	115.5 (4)
C21'—C20'—H20C	109.3	C11—C12—C13	118.7 (4)
O4—C20'—H20D	109.3	C8—C13—C12	122.3 (4)
C21'—C20'—H20D	109.3	C8—C13—H13	118.9
H20C—C20'—H20D	108.0	C12—C13—H13	118.9
C22'—C21'—C20'	116.2	O3—C14—C15	107.5 (3)
C22'—C21'—H21C	108.2	O3—C14—H14A	110.2
C20'—C21'—H21C	108.2	C15—C14—H14A	110.2
C22'—C21'—H21D	108.2	O3—C14—H14B	110.2
C20'—C21'—H21D	108.2	C15—C14—H14B	110.2
H21C—C21'—H21D	107.4	H14A—C14—H14B	108.5
C23'—C22'—C21'	116.0	C14—C15—C16	113.6 (4)
C23'—C22'—H22C	108.3	C14—C15—H15A	108.9
C21'—C22'—H22C	108.3	C16—C15—H15A	108.9
C23'—C22'—H22D	108.3	C14—C15—H15B	108.9
C21'—C22'—H22D	108.3	C16—C15—H15B	108.9
H22C—C22'—H22D	107.4	H15A—C15—H15B	107.7
C24'—C23'—C22'	116.4	C15—C16—C17	112.8 (3)
C24'—C23'—H23C	108.2	C15—C16—H16A	109.0
C22'—C23'—H23C	108.2	C17—C16—H16A	109.0
C24'—C23'—H23D	108.2	C15—C16—H16B	109.0
C22'—C23'—H23D	108.2	C17—C16—H16B	109.0
H23C—C23'—H23D	107.3	H16A—C16—H16B	107.8
C23'—C24'—C25'	116.4	C18—C17—C16	113.8 (4)
C23'—C24'—H24C	108.2	C18—C17—H17A	108.8
C25'—C24'—H24C	108.2	C16—C17—H17A	108.8
C23'—C24'—H24D	108.2	C18—C17—H17B	108.8
C25'—C24'—H24D	108.2	C16—C17—H17B	108.8
H24C—C24'—H24D	107.4	H17A—C17—H17B	107.7
C24'—C25'—H25D	109.5	C17—C18—C19	114.2 (4)
C24'—C25'—H25E	109.5	C17—C18—H18A	108.7
H25D—C25'—H25E	109.5	C19—C18—H18A	108.7
C24'—C25'—H25F	109.5	C17—C18—H18B	108.7
H25D—C25'—H25F	109.5	C19—C18—H18B	108.7
H25E—C25'—H25F	109.5	H18A—C18—H18B	107.6
C1—O1—H1	109.5	C18—C19—H19A	109.5
C12—O3—C14	117.7 (3)	C18—C19—H19B	109.5
C9—O4—C20'	118.6 (3)	H19A—C19—H19B	109.5
C9—O4—C20	119.1 (3)	C18—C19—H19C	109.5
O2—C1—O1	123.6 (4)	H19A—C19—H19C	109.5
O2—C1—C2	120.7 (4)	H19B—C19—H19C	109.5
O1—C1—C2	115.7 (4)
O4—C20—C21—C22	−49.3 (6)	C6—C5—C8—C13	−43.6 (5)
C20—C21—C22—C23	−179.6	C4—C5—C8—C9	−45.5 (5)
C21—C22—C23—C24	−72.3	C6—C5—C8—C9	136.4 (4)
C22—C23—C24—C25	−173.4	C20'—O4—C9—C10	20.1 (6)
O4—C20'—C21'—C22'	46.6 (6)	C20—O4—C9—C10	−1.4 (6)
C20'—C21'—C22'—C23'	169.9	C20'—O4—C9—C8	−158.2 (3)
C21'—C22'—C23'—C24'	124.5	C20—O4—C9—C8	−179.7 (3)
C22'—C23'—C24'—C25'	174.2	C13—C8—C9—O4	177.3 (3)
C21'—C20'—O4—C9	163.6 (3)	C5—C8—C9—O4	−2.6 (5)
C21'—C20'—O4—C20	−99.5 (2)	C13—C8—C9—C10	−1.0 (5)
C21—C20—O4—C9	−173.0 (3)	C5—C8—C9—C10	179.1 (3)
C21—C20—O4—C20'	93.5 (2)	O4—C9—C10—C11	−178.1 (3)
O2—C1—C2—C7	175.5 (4)	C8—C9—C10—C11	0.1 (6)
O1—C1—C2—C7	−6.7 (5)	C9—C10—C11—C12	1.0 (6)
O2—C1—C2—C3	−6.8 (5)	C14—O3—C12—C11	−2.8 (5)
O1—C1—C2—C3	171.1 (3)	C14—O3—C12—C13	178.3 (3)
C7—C2—C3—C4	0.1 (5)	C10—C11—C12—O3	180.0 (3)
C1—C2—C3—C4	−177.7 (3)	C10—C11—C12—C13	−1.1 (6)
C2—C3—C4—C5	0.6 (5)	C9—C8—C13—C12	0.9 (5)
C3—C4—C5—C6	−1.3 (5)	C5—C8—C13—C12	−179.2 (3)
C3—C4—C5—C8	−179.6 (3)	O3—C12—C13—C8	179.2 (3)
C4—C5—C6—C7	1.4 (5)	C11—C12—C13—C8	0.2 (5)
C8—C5—C6—C7	179.7 (3)	C12—O3—C14—C15	179.1 (3)
C3—C2—C7—C6	0.0 (5)	O3—C14—C15—C16	−176.5 (3)
C1—C2—C7—C6	177.7 (3)	C14—C15—C16—C17	−176.9 (3)
C5—C6—C7—C2	−0.8 (5)	C15—C16—C17—C18	178.0 (3)
C4—C5—C8—C13	134.6 (4)	C16—C17—C18—C19	178.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.82	2.632 (4)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.82	2.632 (4)	174

Symmetry code: (i) .