4-(2,5-Dihexyl­oxyphen­yl)benzoic acid

Li, H.; Zhang, L.; Liu, Y.-Q.; Mao, D.-B.; Zhang, W.-Y.

doi:10.1107/S1600536808032170

4-(2,5-Dihexyloxyphenyl)benzoic acid

H. Li, L. Zhang, Y.-Q. Liu, D.-B. Mao and W.-Y. Zhang

In the title compound, C₂₅H₃₄O₄, one n-hexyl chain of the hexyloxy 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, intermolecular O—H

O hydrogen bonds form dimers via crystallographic inversion centres.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808032170/si2116sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808032170/si2116Isup2.hkl Contains datablock I

CCDC reference: 709337

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.061
wR factor = 0.194
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         33 Perc.

Alert level C
            Value of measurement temperature given =   295.000
            Value of melting point given =     0.000
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C23    --  C24     ..       5.30 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C24    --  C25     ..       5.11 su
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Palladium-catalyzed Suzuki coupling reaction has become an extremely powerful method in synthesis for the formation of carbon-carbon bond (Kotha et al., 2002). For example, 1,4-Dibromide-2,5-bis(hexyloxy)benzene was reacted with 4-carboxyphenylboronic acid in the presence of Pd(PPh₃)₄ to give coupling product 2,5-bis(hexyloxy)-1,4-di(4'-carboxyphenyl)benzene (Zhang et al., 2006). In the above reaction, we obtained the title compound as a side product.

A view of the molecular structure of the title compound is given in Fig.1. The dihedral angle between benzene rings is 44.5 (3)°. One n-hexyl chain of the hexyloxyl group has the same fully extended all - trans conformation as the 1,4-Dibromide-2,5-bis(hexyloxy)benzene (Li, et al., 2008), while the other n-hexyl chain displays disorder with site occupancies 0.470 (3) and 0.530 (3). In the crystal structure, centrosymmetric dimers arise from pairs of O—H···O hydrogen bonds involving the carboxylic acid groups (Fig.2, Table 1).

Related literature top

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 top

1,4-Dibromo-2,5-bis(hexyloxy)benzene was prepared as described in the literature (Maruyama & Kawanishi 2002). The title compound was obtained as a side-product from the Suzuki coupling reaction of 1,4-Dibromo-2,5-bis(hexyloxy)benzene and 4-carboxyphenylboronic acid as described in the literature (Zhang et al., 2006) and recrystallized from ethanol at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level. The disordered components are shown.
	Fig. 2. The dimeric structure of the title compound linked by the O—H···O hydrogen bonds.

4-(2,5-Dihexyloxyphenyl)benzoic acid top

Crystal data top

C₂₅H₃₄O₄	F(000) = 864
M_r = 398.52	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0705P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
4359 reflections	Δρ_max = 0.16 e Å⁻³
257 parameters	Δρ_min = −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)

Crystal data top

C₂₅H₃₄O₄	V = 2361.7 (7) Å³
M_r = 398.52	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2936 (12) Å	µ = 0.07 mm⁻¹
b = 14.689 (2) Å	T = 295 K
c = 22.137 (4) Å	0.35 × 0.15 × 0.06 mm
β = 95.283 (3)°

Data collection top

Bruker SMART CCD diffractometer	4359 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1432 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.996	R_int = 0.087
15777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.194	H-atom parameters constrained
S = 0.97	Δρ_max = 0.16 e Å⁻³
4359 reflections	Δρ_min = −0.14 e Å⁻³
257 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₃₄O₄
M_r	398.52
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	7.2936 (12), 14.689 (2), 22.137 (4)
β (°)	95.283 (3)
V (Å³)	2361.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.35 × 0.15 × 0.06

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	15777, 4359, 1432
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.194, 0.97
No. of reflections	4359
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).