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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2094.
Published online 2008 October 11. doi:  10.1107/S1600536808032170
PMCID: PMC2959701

4-(2,5-Dihexyl­oxyphen­yl)benzoic acid

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-o2094-scheme1.jpg

Experimental

Crystal data

  • C25H34O4
  • M r = 398.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2094-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

This work was supported by the Doctoral Foundation of Zhengzhou University of Light Industry.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

H atoms attached to C atoms of the title compound were placed in geometrically idealized positions and treated as riding with C—H distances constrained to 0.93 (aromatic CH), or 0.96 Å (methyl CH3), and 0.97 Å (methylene CH2) and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C) (1.5Ueq for methyl H).

Figures

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.

Crystal data

C25H34O4F(000) = 864
Mr = 398.52Dx = 1.121 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.2936 (12) ÅCell parameters from 918 reflections
b = 14.689 (2) Åθ = 2.8–17.8°
c = 22.137 (4) ŵ = 0.07 mm1
β = 95.283 (3)°T = 295 K
V = 2361.7 (7) Å3Block, colourless
Z = 40.35 × 0.15 × 0.06 mm

Data collection

Bruker SMART CCD diffractometer4359 independent reflections
Radiation source: fine-focus sealed tube1432 reflections with I > 2σ(I)
graphiteRint = 0.087
[var phi] and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.975, Tmax = 0.996k = −17→17
15777 measured reflectionsl = −26→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.194w = 1/[σ2(Fo2) + (0.0705P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
4359 reflectionsΔρmax = 0.16 e Å3
257 parametersΔρmin = −0.14 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (13)

Special details

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.

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

xyzUiso*/UeqOcc. (<1)
C200.7088 (7)0.0256 (3)0.2574 (2)0.1007 (16)0.470 (3)
H20A0.7986−0.02080.27030.121*0.470 (3)
H20B0.68370.02160.21360.121*0.470 (3)
C210.5320 (5)0.0098 (4)0.28753 (19)0.108 (3)0.470 (3)
H21A0.43500.04760.26790.129*0.470 (3)
H21B0.4949−0.05330.28210.129*0.470 (3)
C220.5551 (5)0.0315 (5)0.35456 (16)0.137 (4)0.470 (3)
H22A0.59290.09460.35940.165*0.470 (3)
H22B0.6542−0.00580.37340.165*0.470 (3)
C230.3866 (6)0.0171 (4)0.3885 (2)0.155 (4)0.470 (3)
H23A0.3371−0.04290.37870.187*0.470 (3)
H23B0.42410.01830.43170.187*0.470 (3)
C240.2371 (8)0.0856 (3)0.3751 (2)0.162 (3)0.470 (3)
H24A0.19010.07950.33280.195*0.470 (3)
H24B0.29020.14600.38030.195*0.470 (3)
C250.0785 (8)0.0786 (4)0.4134 (2)0.153 (3)0.470 (3)
H25A−0.01920.04450.39200.229*0.470 (3)
H25B0.03530.13860.42190.229*0.470 (3)
H25C0.11800.04830.45080.229*0.470 (3)
C20'0.7495 (6)0.0177 (3)0.2742 (2)0.1007 (16)0.530 (3)
H20C0.8659−0.01350.28350.121*0.530 (3)
H20D0.6987−0.00160.23420.121*0.530 (3)
C21'0.6199 (6)−0.0085 (3)0.3200 (2)0.108 (3)0.530 (3)
H21C0.5838−0.07140.31290.129*0.530 (3)
H21D0.6861−0.00530.36000.129*0.530 (3)
C22'0.4489 (5)0.0478 (2)0.32045 (16)0.137 (4)0.530 (3)
H22C0.48390.10830.33470.165*0.530 (3)
H22D0.39420.05370.27900.165*0.530 (3)
C23'0.3055 (5)0.0122 (3)0.3584 (2)0.155 (4)0.530 (3)
H23C0.1984−0.00480.33150.187*0.530 (3)
H23D0.3527−0.04270.37850.187*0.530 (3)
C24'0.2443 (6)0.0752 (3)0.4053 (2)0.162 (3)0.530 (3)
H24C0.20900.13250.38580.195*0.530 (3)
H24D0.34870.08730.43460.195*0.530 (3)
C25'0.0875 (7)0.0431 (4)0.4391 (3)0.153 (3)0.530 (3)
H25D0.0275−0.00730.41800.229*0.530 (3)
H25E0.00090.09180.44190.229*0.530 (3)
H25F0.13360.02420.47920.229*0.530 (3)
O10.7303 (4)0.4749 (2)0.48474 (13)0.1015 (9)
H10.66430.49510.50970.152*
O20.4582 (4)0.45546 (17)0.43055 (11)0.0937 (9)
O31.3854 (4)0.25963 (18)0.17662 (11)0.0957 (9)
O40.7809 (4)0.11432 (17)0.27390 (12)0.1056 (10)
C10.6290 (7)0.4451 (3)0.43801 (19)0.0811 (12)
C20.7271 (6)0.3934 (2)0.39327 (17)0.0735 (10)
C30.6246 (5)0.3488 (3)0.34666 (18)0.0766 (11)
H30.49690.35350.34320.092*
C40.7099 (6)0.2974 (2)0.30537 (16)0.0774 (11)
H40.63840.26840.27410.093*
C50.9002 (6)0.2878 (2)0.30924 (16)0.0692 (10)
C61.0009 (5)0.3342 (3)0.35605 (18)0.0835 (12)
H61.12870.33030.35930.100*
C70.9163 (6)0.3863 (3)0.39816 (17)0.0832 (11)
H70.98690.41600.42930.100*
C80.9934 (5)0.2331 (3)0.26465 (15)0.0720 (10)
C90.9291 (6)0.1468 (3)0.24652 (17)0.0810 (11)
C101.0170 (6)0.0979 (3)0.20426 (17)0.0909 (12)
H100.97340.04060.19230.109*
C111.1685 (6)0.1332 (3)0.17971 (17)0.0892 (12)
H111.22520.10010.15090.107*
C121.2361 (6)0.2173 (3)0.19762 (17)0.0791 (11)
C131.1469 (5)0.2661 (3)0.23992 (15)0.0761 (11)
H131.19220.32310.25200.091*
C141.4854 (6)0.2112 (3)0.13414 (17)0.0936 (12)
H14A1.40470.19590.09830.112*
H14B1.53510.15520.15220.112*
C151.6382 (5)0.2718 (3)0.11761 (17)0.0939 (12)
H15A1.71970.28420.15380.113*
H15B1.58630.32930.10290.113*
C161.7496 (6)0.2318 (3)0.06986 (17)0.1004 (13)
H16A1.66980.22250.03280.120*
H16B1.79640.17270.08350.120*
C171.9103 (6)0.2919 (3)0.05617 (17)0.0987 (13)
H17A1.86270.35020.04130.118*
H17B1.98720.30280.09360.118*
C182.0261 (6)0.2524 (3)0.01070 (19)0.1182 (16)
H18A1.94850.2401−0.02640.142*
H18B2.07570.19470.02600.142*
C192.1840 (6)0.3126 (3)−0.0042 (2)0.1344 (18)
H19A2.13600.3676−0.02300.202*
H19B2.25690.2812−0.03150.202*
H19C2.25910.32730.03240.202*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C200.121 (4)0.072 (3)0.111 (4)−0.021 (3)0.019 (3)−0.011 (3)
C210.089 (7)0.075 (4)0.163 (8)0.001 (4)0.031 (6)−0.007 (5)
C220.124 (8)0.105 (5)0.191 (10)0.015 (5)0.057 (7)0.039 (6)
C230.119 (7)0.115 (5)0.241 (10)0.004 (5)0.063 (7)0.002 (6)
C240.217 (8)0.172 (7)0.096 (7)0.008 (6)0.006 (6)0.023 (6)
C250.112 (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)
O10.102 (2)0.112 (2)0.094 (2)−0.0008 (18)0.0274 (17)−0.0269 (18)
O20.095 (2)0.103 (2)0.0856 (19)0.0112 (18)0.0216 (17)−0.0026 (16)
O30.099 (2)0.097 (2)0.0964 (19)−0.0086 (17)0.0363 (17)−0.0176 (16)
O40.120 (2)0.0675 (18)0.137 (2)−0.0163 (17)0.052 (2)−0.0183 (17)
C10.096 (4)0.082 (3)0.069 (3)−0.008 (3)0.022 (3)0.002 (2)
C20.084 (3)0.069 (2)0.070 (3)−0.001 (2)0.023 (2)−0.003 (2)
C30.080 (3)0.074 (3)0.077 (3)0.000 (2)0.017 (2)0.003 (2)
C40.081 (3)0.075 (3)0.078 (3)−0.007 (2)0.011 (2)−0.002 (2)
C50.080 (3)0.057 (2)0.071 (3)−0.001 (2)0.009 (2)−0.001 (2)
C60.070 (3)0.089 (3)0.093 (3)0.001 (2)0.017 (2)−0.012 (2)
C70.087 (3)0.087 (3)0.078 (3)−0.006 (2)0.017 (2)−0.014 (2)
C80.083 (3)0.063 (3)0.071 (2)0.004 (2)0.014 (2)−0.007 (2)
C90.094 (3)0.068 (3)0.084 (3)−0.004 (2)0.023 (2)−0.005 (2)
C100.120 (4)0.069 (3)0.087 (3)−0.010 (3)0.024 (3)−0.014 (2)
C110.108 (3)0.085 (3)0.078 (3)−0.001 (3)0.026 (2)−0.013 (2)
C120.083 (3)0.077 (3)0.080 (3)−0.002 (3)0.017 (2)−0.005 (2)
C130.084 (3)0.071 (3)0.075 (2)0.002 (2)0.012 (2)−0.012 (2)
C140.106 (3)0.093 (3)0.086 (3)0.005 (3)0.031 (3)−0.012 (2)
C150.095 (3)0.100 (3)0.089 (3)0.004 (3)0.021 (3)−0.004 (3)
C160.099 (3)0.110 (3)0.096 (3)0.002 (3)0.028 (3)−0.020 (3)
C170.100 (3)0.104 (3)0.096 (3)0.002 (3)0.031 (3)−0.016 (2)
C180.110 (4)0.129 (4)0.121 (4)0.001 (3)0.041 (3)−0.030 (3)
C190.117 (4)0.154 (5)0.139 (4)−0.019 (3)0.049 (3)−0.025 (3)

Geometric parameters (Å, °)

C20—O41.440 (5)O3—C141.432 (4)
C20—C211.5236 (17)O4—C91.372 (4)
C20—H20A0.9700C1—C21.483 (5)
C20—H20B0.9700C2—C71.378 (4)
C21—C221.5119 (17)C2—C31.383 (4)
C21—H21A0.9700C3—C41.378 (4)
C21—H21B0.9700C3—H30.9300
C22—C231.5129 (17)C4—C51.390 (4)
C22—H22A0.9700C4—H40.9300
C22—H22B0.9700C5—C61.392 (4)
C23—C241.4930 (17)C5—C81.486 (4)
C23—H23A0.9700C6—C71.393 (4)
C23—H23B0.9700C6—H60.9300
C24—C251.4994 (17)C7—H70.9300
C24—H24A0.9700C8—C131.379 (4)
C24—H24B0.9700C8—C91.397 (5)
C25—H25A0.9600C9—C101.383 (5)
C25—H25B0.9600C10—C111.377 (5)
C25—H25C0.9600C10—H100.9300
C20'—O41.438 (4)C11—C121.374 (5)
C20'—C21'1.4978 (17)C11—H110.9300
C20'—H20C0.9700C12—C131.388 (4)
C20'—H20D0.9700C13—H130.9300
C21'—C22'1.4966 (17)C14—C151.498 (5)
C21'—H21C0.9700C14—H14A0.9700
C21'—H21D0.9700C14—H14B0.9700
C22'—C23'1.4938 (17)C15—C161.510 (4)
C22'—H22C0.9700C15—H15A0.9700
C22'—H22D0.9700C15—H15B0.9700
C23'—C24'1.4906 (17)C16—C171.520 (5)
C23'—H23C0.9700C16—H16A0.9700
C23'—H23D0.9700C16—H16B0.9700
C24'—C25'1.4994 (17)C17—C181.490 (4)
C24'—H24C0.9700C17—H17A0.9700
C24'—H24D0.9700C17—H17B0.9700
C25'—H25D0.9600C18—C191.513 (5)
C25'—H25E0.9600C18—H18A0.9700
C25'—H25F0.9600C18—H18B0.9700
O1—C11.291 (4)C19—H19A0.9600
O1—H10.8200C19—H19B0.9600
O2—C11.251 (4)C19—H19C0.9600
O3—C121.372 (4)
O4—C20—C21109.3 (2)C7—C2—C3119.4 (4)
O4—C20—H20A109.8C7—C2—C1121.8 (4)
C21—C20—H20A109.8C3—C2—C1118.7 (4)
O4—C20—H20B109.8C4—C3—C2120.6 (4)
C21—C20—H20B109.8C4—C3—H3119.7
H20A—C20—H20B108.3C2—C3—H3119.7
C22—C21—C20112.1C3—C4—C5121.6 (4)
C22—C21—H21A109.2C3—C4—H4119.2
C20—C21—H21A109.2C5—C4—H4119.2
C22—C21—H21B109.2C4—C5—C6116.9 (3)
C20—C21—H21B109.2C4—C5—C8121.9 (4)
H21A—C21—H21B107.9C6—C5—C8121.2 (4)
C21—C22—C23115.8C5—C6—C7122.1 (4)
C21—C22—H22A108.3C5—C6—H6119.0
C23—C22—H22A108.3C7—C6—H6119.0
C21—C22—H22B108.3C2—C7—C6119.4 (4)
C23—C22—H22B108.3C2—C7—H7120.3
H22A—C22—H22B107.4C6—C7—H7120.3
C24—C23—C22114.8C13—C8—C9118.0 (3)
C24—C23—H23A108.6C13—C8—C5120.7 (4)
C22—C23—H23A108.6C9—C8—C5121.3 (4)
C24—C23—H23B108.6O4—C9—C10123.4 (4)
C22—C23—H23B108.6O4—C9—C8116.5 (4)
H23A—C23—H23B107.5C10—C9—C8120.1 (4)
C23—C24—C25115.4C11—C10—C9120.7 (4)
C23—C24—H24A108.4C11—C10—H10119.7
C25—C24—H24A108.4C9—C10—H10119.7
C23—C24—H24B108.4C12—C11—C10120.3 (4)
C25—C24—H24B108.4C12—C11—H11119.9
H24A—C24—H24B107.5C10—C11—H11119.9
O4—C20'—C21'111.6 (2)O3—C12—C11125.8 (4)
O4—C20'—H20C109.3O3—C12—C13115.5 (4)
C21'—C20'—H20C109.3C11—C12—C13118.7 (4)
O4—C20'—H20D109.3C8—C13—C12122.3 (4)
C21'—C20'—H20D109.3C8—C13—H13118.9
H20C—C20'—H20D108.0C12—C13—H13118.9
C22'—C21'—C20'116.2O3—C14—C15107.5 (3)
C22'—C21'—H21C108.2O3—C14—H14A110.2
C20'—C21'—H21C108.2C15—C14—H14A110.2
C22'—C21'—H21D108.2O3—C14—H14B110.2
C20'—C21'—H21D108.2C15—C14—H14B110.2
H21C—C21'—H21D107.4H14A—C14—H14B108.5
C23'—C22'—C21'116.0C14—C15—C16113.6 (4)
C23'—C22'—H22C108.3C14—C15—H15A108.9
C21'—C22'—H22C108.3C16—C15—H15A108.9
C23'—C22'—H22D108.3C14—C15—H15B108.9
C21'—C22'—H22D108.3C16—C15—H15B108.9
H22C—C22'—H22D107.4H15A—C15—H15B107.7
C24'—C23'—C22'116.4C15—C16—C17112.8 (3)
C24'—C23'—H23C108.2C15—C16—H16A109.0
C22'—C23'—H23C108.2C17—C16—H16A109.0
C24'—C23'—H23D108.2C15—C16—H16B109.0
C22'—C23'—H23D108.2C17—C16—H16B109.0
H23C—C23'—H23D107.3H16A—C16—H16B107.8
C23'—C24'—C25'116.4C18—C17—C16113.8 (4)
C23'—C24'—H24C108.2C18—C17—H17A108.8
C25'—C24'—H24C108.2C16—C17—H17A108.8
C23'—C24'—H24D108.2C18—C17—H17B108.8
C25'—C24'—H24D108.2C16—C17—H17B108.8
H24C—C24'—H24D107.4H17A—C17—H17B107.7
C24'—C25'—H25D109.5C17—C18—C19114.2 (4)
C24'—C25'—H25E109.5C17—C18—H18A108.7
H25D—C25'—H25E109.5C19—C18—H18A108.7
C24'—C25'—H25F109.5C17—C18—H18B108.7
H25D—C25'—H25F109.5C19—C18—H18B108.7
H25E—C25'—H25F109.5H18A—C18—H18B107.6
C1—O1—H1109.5C18—C19—H19A109.5
C12—O3—C14117.7 (3)C18—C19—H19B109.5
C9—O4—C20'118.6 (3)H19A—C19—H19B109.5
C9—O4—C20119.1 (3)C18—C19—H19C109.5
O2—C1—O1123.6 (4)H19A—C19—H19C109.5
O2—C1—C2120.7 (4)H19B—C19—H19C109.5
O1—C1—C2115.7 (4)
O4—C20—C21—C22−49.3 (6)C6—C5—C8—C13−43.6 (5)
C20—C21—C22—C23−179.6C4—C5—C8—C9−45.5 (5)
C21—C22—C23—C24−72.3C6—C5—C8—C9136.4 (4)
C22—C23—C24—C25−173.4C20'—O4—C9—C1020.1 (6)
O4—C20'—C21'—C22'46.6 (6)C20—O4—C9—C10−1.4 (6)
C20'—C21'—C22'—C23'169.9C20'—O4—C9—C8−158.2 (3)
C21'—C22'—C23'—C24'124.5C20—O4—C9—C8−179.7 (3)
C22'—C23'—C24'—C25'174.2C13—C8—C9—O4177.3 (3)
C21'—C20'—O4—C9163.6 (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—C10179.1 (3)
C21—C20—O4—C20'93.5 (2)O4—C9—C10—C11−178.1 (3)
O2—C1—C2—C7175.5 (4)C8—C9—C10—C110.1 (6)
O1—C1—C2—C7−6.7 (5)C9—C10—C11—C121.0 (6)
O2—C1—C2—C3−6.8 (5)C14—O3—C12—C11−2.8 (5)
O1—C1—C2—C3171.1 (3)C14—O3—C12—C13178.3 (3)
C7—C2—C3—C40.1 (5)C10—C11—C12—O3180.0 (3)
C1—C2—C3—C4−177.7 (3)C10—C11—C12—C13−1.1 (6)
C2—C3—C4—C50.6 (5)C9—C8—C13—C120.9 (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—C8179.2 (3)
C4—C5—C6—C71.4 (5)C11—C12—C13—C80.2 (5)
C8—C5—C6—C7179.7 (3)C12—O3—C14—C15179.1 (3)
C3—C2—C7—C60.0 (5)O3—C14—C15—C16−176.5 (3)
C1—C2—C7—C6177.7 (3)C14—C15—C16—C17−176.9 (3)
C5—C6—C7—C2−0.8 (5)C15—C16—C17—C18178.0 (3)
C4—C5—C8—C13134.6 (4)C16—C17—C18—C19178.7 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.822.632 (4)174

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2116).

References

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