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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1521.
Published online 2010 June 5. doi:  10.1107/S1600536810019227
PMCID: PMC3006914

4,4′-[2,5-Bis(dodec­yloxy)-p-phenyl­ene]bis­(2-methyl­but-3-yn-2-ol)

Abstract

In the title compound, C40H66O4, the C and O atoms of the propinyl and dodecoxyl substituents are nearly coplanar with the benzene ring, 1.735 (6), 8.804 (1), 8.786 (1) and 9.577 (3)°, respectively. In the crystal, mol­ecules are connected by inter­molecular O—H(...)O hydrogen bonds.

Related literature

The title compound is an important inter­mediate for the preparation of π-conjugated polymers and supra­molecular architectures, see Fang et al. (2006 [triangle]); Chou et al. (2010 [triangle]); Mahesh et al. (2009 [triangle]). For background to polyaryl­eneethynylenes (PAEs) and their properties and applications, see: Bunz (2000 [triangle], 2005 [triangle]); Cheng & Luh (2004 [triangle]); Zhan et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1521-scheme1.jpg

Experimental

Crystal data

  • C40H66O4
  • M r = 610.93
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1521-efi1.jpg
  • a = 9.1325 (9) Å
  • b = 9.707 (1) Å
  • c = 22.9107 (19) Å
  • α = 85.810 (1)°
  • β = 88.512 (2)°
  • γ = 79.373 (1)°
  • V = 1990.7 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.06 mm−1
  • T = 298 K
  • 0.49 × 0.45 × 0.44 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002 [triangle]) T min = 0.970, T max = 0.973
  • 10561 measured reflections
  • 6920 independent reflections
  • 2398 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.071
  • wR(F 2) = 0.166
  • S = 1.07
  • 6920 reflections
  • 404 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019227/vm2027sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019227/vm2027Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (50633020 and 50603015) and the National Basic Research Program of China (National 973 program, No. 2005CB623903).

supplementary crystallographic information

Comment

In the past decade, a family of π-conjugated polymers such as polyaryleneethynylenes (PAEs) have been extensively studied (Bunz, 2000). These compounds usually show functional properities such as photoluminescence (Bunz, 2000) or electroluminescence (Zhan, 2001), and can be used as electronic and photonic devices (Cheng, 2004; Bunz 2005). We have prepared the novel title compound, (I), based on 1,4-dibromo-2,5-bis(dodecyloxy)benzene and 2-methylbut-3-yn-2-ol. It is an important intermediate for the preparation of π-conjugated polymers (Fang et al., 2006) and supramolecular architectures (Chou et al..,2010; Mahesh et al..,2009). In the title compoud, all the C, O atoms of propinyl and dodecoxyl are almost coplanar with the benzene ring. The two dodecyloxy chains show a nice zigzag conformation (Fig. 1). In the crystal, molecules are connected by O—H···O hydrogen bonds and the two benzene rings are parallel in the monoclinic unit cell (Fig. 2).

Experimental

The title compound was obtained by adding 1,4-dibromo-2,5-bis(dodecyloxy)benzene (10.00 g, 16.54 mmol), triethylamine (80 ml), PdCl2(PPh3)2 (1.16 g, 1.65 mmol), PPh3 (2.16 g, 8.25 mmol), 2-methylbut-3-yn-2-ol (3.48 g, 41.35 mmol) and CuI (0.30 g, 1.65 mmol) into a 250 ml three-necked flask. The mixture was heated in an oil bath to reflux for 20 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. Colourless acicular crystals of the title compound were grown by slow evaporation of an ethanol solution at room temperature. (8.10 g, 80% yield, m.p. 368 K-370 K). Analysis calculated for C40H66O4: C, 78.64; H, 10.89; found: C, 78.60; H, 10.80%.

Refinement

H atoms bound to C atoms and O atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic C), C—H = 0.97 Å (methylene C), C—H = 0.96 Å (methyl C), O—H = 0.82 Å and with Uiso(H) = 1.2Ueq(C, O).

Figures

Fig. 1.
The molecular structure of the title compound showing the atomic numbering and 30% probability displacement ellipsoids.
Fig. 2.
Packinig diagram of the title compound with hydrogen bonds drawn as dashed lines.

Crystal data

C40H66O4Z = 2
Mr = 610.93F(000) = 676
Triclinic, P1Dx = 1.019 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1325 (9) ÅCell parameters from 1230 reflections
b = 9.707 (1) Åθ = 2.4–20.8°
c = 22.9107 (19) ŵ = 0.06 mm1
α = 85.810 (1)°T = 298 K
β = 88.512 (2)°Acicular, colorless
γ = 79.373 (1)°0.49 × 0.45 × 0.44 mm
V = 1990.7 (3) Å3

Data collection

Bruker SMART CCD area-detector diffractometer6920 independent reflections
Radiation source: fine-focus sealed tube2398 reflections with I > 2σ(I)
graphiteRint = 0.042
phi and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)h = −10→9
Tmin = 0.970, Tmax = 0.973k = −11→11
10561 measured reflectionsl = −27→27

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071H-atom parameters constrained
wR(F2) = 0.166w = 1/[σ2(Fo2) + (0.0353P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
6920 reflectionsΔρmax = 0.18 e Å3
404 parametersΔρmin = −0.21 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: 0.0060 (6)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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*/Ueq
O10.5619 (2)0.6464 (2)0.60317 (9)0.0666 (7)
O20.4531 (2)0.8819 (2)0.37806 (9)0.0714 (7)
O31.0800 (2)0.7198 (2)0.62786 (11)0.0994 (9)
H31.03110.65720.63390.119*
O40.1121 (2)0.4803 (2)0.35258 (8)0.0752 (7)
H40.19640.45270.36520.090*
C10.5291 (3)0.7034 (3)0.54744 (14)0.0534 (8)
C20.6249 (3)0.7888 (3)0.52315 (13)0.0528 (8)
C30.5991 (3)0.8499 (3)0.46641 (13)0.0572 (9)
H3A0.66270.90730.45010.069*
C40.4830 (3)0.8276 (3)0.43423 (14)0.0533 (8)
C50.3887 (3)0.7413 (3)0.45894 (14)0.0551 (9)
C60.4118 (3)0.6820 (3)0.51588 (13)0.0584 (9)
H60.34630.62700.53260.070*
C70.7507 (3)0.8120 (3)0.55566 (13)0.0582 (9)
C80.8540 (3)0.8312 (3)0.58160 (14)0.0602 (9)
C90.9813 (4)0.8515 (4)0.61596 (15)0.0635 (9)
C101.0743 (4)0.9431 (3)0.58122 (14)0.0930 (13)
H10A1.15870.95210.60380.139*
H10B1.01521.03440.57230.139*
H10C1.10820.90100.54550.139*
C110.9265 (4)0.9115 (4)0.67326 (14)0.0987 (13)
H11A0.87380.84750.69520.148*
H11B0.86091.00000.66560.148*
H11C1.01000.92500.69540.148*
C120.2687 (3)0.7079 (3)0.42565 (13)0.0601 (9)
C130.1735 (4)0.6704 (3)0.40058 (13)0.0623 (10)
C140.0546 (4)0.6191 (3)0.37183 (15)0.0643 (9)
C150.0049 (4)0.7068 (4)0.31614 (15)0.1171 (16)
H15A0.09020.71550.29180.176*
H15B−0.04540.79840.32570.176*
H15C−0.06180.66200.29570.176*
C16−0.0720 (4)0.6081 (4)0.41370 (17)0.1193 (15)
H16A−0.14700.57050.39470.179*
H16B−0.11390.69960.42610.179*
H16C−0.03620.54690.44720.179*
C170.4571 (3)0.5688 (3)0.63136 (12)0.0651 (9)
H17A0.45070.48790.60970.078*
H17B0.35910.62770.63240.078*
C180.5082 (3)0.5217 (3)0.69225 (12)0.0682 (10)
H18A0.52150.60260.71260.082*
H18B0.60380.45870.69070.082*
C190.3975 (3)0.4474 (3)0.72566 (12)0.0768 (11)
H19A0.30270.51140.72730.092*
H19B0.38280.36820.70440.092*
C200.4440 (4)0.3951 (3)0.78700 (13)0.0808 (11)
H20A0.46420.47350.80750.097*
H20B0.53630.32740.78510.097*
C210.3313 (4)0.3275 (4)0.82205 (13)0.0951 (13)
H21A0.31140.24900.80160.114*
H21B0.23900.39520.82370.114*
C220.3764 (4)0.2753 (4)0.88363 (14)0.0943 (12)
H22A0.46780.20650.88180.113*
H22B0.39850.35350.90360.113*
C230.2654 (4)0.2106 (4)0.91963 (14)0.1057 (14)
H23A0.17400.27940.92120.127*
H23B0.24350.13240.89950.127*
C240.3075 (4)0.1586 (4)0.98064 (14)0.1027 (14)
H24A0.39720.08760.97900.123*
H24B0.33250.23611.00040.123*
C250.1960 (4)0.0981 (4)1.01714 (15)0.1141 (15)
H25A0.10670.16951.01870.137*
H25B0.17050.02150.99700.137*
C260.2341 (4)0.0446 (4)1.07781 (15)0.1080 (14)
H26A0.3221−0.02841.07620.130*
H26B0.26180.12061.09770.130*
C270.1228 (5)−0.0124 (5)1.11418 (16)0.1390 (18)
H27A0.0949−0.08791.09400.167*
H27B0.03500.06081.11560.167*
C280.1581 (5)−0.0666 (5)1.17449 (17)0.160 (2)
H28A0.2394−0.14491.17440.241*
H28B0.0724−0.09641.19280.241*
H28C0.18570.00611.19580.241*
C290.5533 (3)0.9638 (3)0.35073 (13)0.0709 (10)
H29A0.65350.90900.35090.085*
H29B0.55361.04600.37240.085*
C300.5069 (4)1.0082 (4)0.28960 (13)0.0813 (11)
H30A0.41281.07350.29020.098*
H30B0.49130.92660.27020.098*
C310.6199 (4)1.0771 (3)0.25481 (13)0.0817 (11)
H31A0.64021.15450.27590.098*
H31B0.71211.00940.25270.098*
C320.5752 (4)1.1317 (4)0.19408 (13)0.0932 (12)
H32A0.55081.05490.17370.112*
H32B0.48501.20180.19650.112*
C330.6870 (4)1.1953 (4)0.15801 (14)0.0944 (12)
H33A0.77691.12500.15540.113*
H33B0.71201.27160.17860.113*
C340.6418 (4)1.2511 (4)0.09735 (14)0.1049 (14)
H34A0.61421.17520.07730.126*
H34B0.55301.32270.10020.126*
C350.7518 (4)1.3120 (4)0.06007 (15)0.1056 (14)
H35A0.77861.38820.08010.127*
H35B0.84101.24050.05780.127*
C360.7107 (4)1.3664 (4)−0.00021 (15)0.1068 (14)
H36A0.68161.2907−0.01990.128*
H36B0.62291.43930.00220.128*
C370.8198 (5)1.4237 (4)−0.03764 (16)0.1198 (16)
H37A0.90721.3503−0.04010.144*
H37B0.84951.4986−0.01760.144*
C380.7808 (5)1.4795 (4)−0.09775 (16)0.1136 (15)
H38A0.74681.4060−0.11730.136*
H38B0.69631.5558−0.09520.136*
C390.8910 (5)1.5306 (5)−0.13537 (18)0.153 (2)
H39A0.97391.4528−0.13840.184*
H39B0.92751.6009−0.11470.184*
C400.8588 (5)1.5906 (5)−0.19420 (18)0.167 (2)
H40A0.83571.5199−0.21780.250*
H40B0.94411.6251−0.21050.250*
H40C0.77521.6667−0.19340.250*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0536 (14)0.0819 (16)0.0665 (15)−0.0259 (13)−0.0131 (12)0.0194 (13)
O20.0585 (15)0.0954 (17)0.0632 (15)−0.0284 (14)−0.0101 (13)0.0144 (13)
O30.0594 (16)0.0710 (17)0.169 (2)−0.0183 (14)−0.0301 (16)0.0092 (17)
O40.0587 (15)0.0705 (16)0.0982 (17)−0.0143 (13)−0.0151 (13)−0.0061 (13)
C10.039 (2)0.056 (2)0.064 (2)−0.0101 (18)−0.0039 (18)0.0030 (18)
C20.0368 (19)0.053 (2)0.067 (2)−0.0070 (17)−0.0014 (18)0.0032 (17)
C30.040 (2)0.063 (2)0.067 (2)−0.0109 (18)0.0037 (18)0.0037 (18)
C40.039 (2)0.056 (2)0.063 (2)−0.0056 (18)−0.0004 (18)−0.0008 (18)
C50.035 (2)0.057 (2)0.074 (2)−0.0103 (18)−0.0073 (19)−0.0011 (19)
C60.044 (2)0.063 (2)0.068 (2)−0.0136 (18)0.0001 (19)0.0074 (19)
C70.050 (2)0.056 (2)0.070 (2)−0.0166 (18)−0.0043 (19)0.0032 (17)
C80.047 (2)0.061 (2)0.074 (2)−0.0148 (18)−0.0034 (19)0.0004 (18)
C90.048 (2)0.060 (2)0.085 (3)−0.019 (2)−0.012 (2)0.003 (2)
C100.076 (3)0.105 (3)0.108 (3)−0.049 (3)−0.011 (2)0.013 (2)
C110.091 (3)0.139 (4)0.076 (3)−0.044 (3)−0.008 (2)−0.012 (3)
C120.049 (2)0.062 (2)0.071 (2)−0.0150 (19)−0.0004 (19)−0.0012 (18)
C130.051 (2)0.063 (2)0.074 (2)−0.0145 (19)−0.003 (2)0.0005 (19)
C140.050 (2)0.059 (2)0.085 (3)−0.010 (2)−0.009 (2)−0.008 (2)
C150.135 (4)0.094 (3)0.127 (3)−0.036 (3)−0.082 (3)0.022 (3)
C160.066 (3)0.148 (4)0.160 (4)−0.045 (3)0.027 (3)−0.062 (3)
C170.049 (2)0.076 (2)0.070 (2)−0.020 (2)−0.0010 (19)0.0098 (19)
C180.055 (2)0.088 (3)0.061 (2)−0.016 (2)−0.0048 (19)0.0107 (19)
C190.058 (2)0.104 (3)0.068 (2)−0.022 (2)0.002 (2)0.012 (2)
C200.071 (3)0.104 (3)0.067 (2)−0.024 (2)−0.003 (2)0.016 (2)
C210.081 (3)0.135 (4)0.071 (3)−0.033 (3)0.001 (2)0.019 (2)
C220.090 (3)0.117 (3)0.075 (3)−0.028 (3)0.001 (2)0.022 (2)
C230.092 (3)0.148 (4)0.076 (3)−0.034 (3)0.000 (2)0.025 (3)
C240.102 (3)0.127 (4)0.076 (3)−0.025 (3)0.001 (3)0.025 (3)
C250.106 (3)0.160 (4)0.075 (3)−0.036 (3)0.004 (3)0.029 (3)
C260.112 (3)0.132 (4)0.077 (3)−0.027 (3)0.001 (3)0.026 (3)
C270.135 (4)0.190 (5)0.088 (3)−0.041 (4)0.015 (3)0.038 (3)
C280.182 (5)0.194 (5)0.096 (3)−0.033 (4)0.010 (3)0.045 (4)
C290.060 (2)0.083 (3)0.071 (2)−0.024 (2)−0.005 (2)0.013 (2)
C300.070 (3)0.110 (3)0.063 (2)−0.022 (2)−0.004 (2)0.016 (2)
C310.077 (3)0.096 (3)0.071 (2)−0.023 (2)−0.004 (2)0.015 (2)
C320.084 (3)0.128 (3)0.066 (2)−0.025 (3)0.002 (2)0.013 (2)
C330.093 (3)0.113 (3)0.077 (3)−0.027 (3)0.000 (2)0.018 (2)
C340.097 (3)0.142 (4)0.075 (3)−0.029 (3)0.002 (3)0.017 (3)
C350.102 (3)0.132 (4)0.083 (3)−0.037 (3)0.001 (3)0.028 (3)
C360.100 (3)0.147 (4)0.073 (3)−0.031 (3)0.003 (3)0.018 (3)
C370.124 (4)0.152 (4)0.084 (3)−0.042 (3)−0.001 (3)0.034 (3)
C380.118 (4)0.147 (4)0.076 (3)−0.034 (3)0.008 (3)0.015 (3)
C390.149 (5)0.209 (5)0.099 (4)−0.053 (4)−0.008 (3)0.053 (4)
C400.180 (5)0.209 (5)0.104 (4)−0.037 (5)0.007 (4)0.036 (4)

Geometric parameters (Å, °)

O1—C11.372 (3)C22—H22B0.9700
O1—C171.436 (3)C23—C241.487 (4)
O2—C41.369 (3)C23—H23A0.9700
O2—C291.424 (3)C23—H23B0.9700
O3—C91.434 (3)C24—C251.478 (4)
O3—H30.8200C24—H24A0.9700
O4—C141.449 (3)C24—H24B0.9700
O4—H40.8200C25—C261.475 (4)
C1—C61.363 (4)C25—H25A0.9700
C1—C21.392 (3)C25—H25B0.9700
C2—C31.396 (3)C26—C271.460 (4)
C2—C71.446 (4)C26—H26A0.9700
C3—C41.365 (4)C26—H26B0.9700
C3—H3A0.9300C27—C281.464 (4)
C4—C51.391 (3)C27—H27A0.9700
C5—C61.392 (3)C27—H27B0.9700
C5—C121.449 (4)C28—H28A0.9600
C6—H60.9300C28—H28B0.9600
C7—C81.178 (4)C28—H28C0.9600
C8—C91.471 (4)C29—C301.484 (3)
C9—C111.511 (4)C29—H29A0.9700
C9—C101.512 (4)C29—H29B0.9700
C10—H10A0.9600C30—C311.511 (3)
C10—H10B0.9600C30—H30A0.9700
C10—H10C0.9600C30—H30B0.9700
C11—H11A0.9600C31—C321.492 (3)
C11—H11B0.9600C31—H31A0.9700
C11—H11C0.9600C31—H31B0.9700
C12—C131.180 (4)C32—C331.490 (4)
C13—C141.465 (4)C32—H32A0.9700
C14—C161.497 (4)C32—H32B0.9700
C14—C151.512 (4)C33—C341.494 (4)
C15—H15A0.9600C33—H33A0.9700
C15—H15B0.9600C33—H33B0.9700
C15—H15C0.9600C34—C351.480 (4)
C16—H16A0.9600C34—H34A0.9700
C16—H16B0.9600C34—H34B0.9700
C16—H16C0.9600C35—C361.475 (4)
C17—C181.495 (3)C35—H35A0.9700
C17—H17A0.9700C35—H35B0.9700
C17—H17B0.9700C36—C371.459 (4)
C18—C191.509 (3)C36—H36A0.9700
C18—H18A0.9700C36—H36B0.9700
C18—H18B0.9700C37—C381.471 (4)
C19—C201.503 (3)C37—H37A0.9700
C19—H19A0.9700C37—H37B0.9700
C19—H19B0.9700C38—C391.442 (4)
C20—C211.505 (4)C38—H38A0.9700
C20—H20A0.9700C38—H38B0.9700
C20—H20B0.9700C39—C401.444 (4)
C21—C221.505 (4)C39—H39A0.9700
C21—H21A0.9700C39—H39B0.9700
C21—H21B0.9700C40—H40A0.9600
C22—C231.489 (4)C40—H40B0.9600
C22—H22A0.9700C40—H40C0.9600
C1—O1—C17116.8 (2)H23A—C23—H23B107.3
C4—O2—C29117.5 (2)C25—C24—C23117.3 (3)
C9—O3—H3109.5C25—C24—H24A108.0
C14—O4—H4109.5C23—C24—H24A108.0
C6—C1—O1124.6 (3)C25—C24—H24B108.0
C6—C1—C2119.7 (3)C23—C24—H24B108.0
O1—C1—C2115.7 (3)H24A—C24—H24B107.2
C1—C2—C3118.9 (3)C26—C25—C24118.9 (3)
C1—C2—C7120.6 (3)C26—C25—H25A107.6
C3—C2—C7120.4 (3)C24—C25—H25A107.6
C4—C3—C2121.7 (3)C26—C25—H25B107.6
C4—C3—H3A119.1C24—C25—H25B107.6
C2—C3—H3A119.1H25A—C25—H25B107.0
C3—C4—O2124.7 (3)C27—C26—C25118.8 (3)
C3—C4—C5118.7 (3)C27—C26—H26A107.6
O2—C4—C5116.5 (3)C25—C26—H26A107.6
C4—C5—C6120.0 (3)C27—C26—H26B107.6
C4—C5—C12121.0 (3)C25—C26—H26B107.6
C6—C5—C12118.9 (3)H26A—C26—H26B107.0
C1—C6—C5120.8 (3)C26—C27—C28119.8 (4)
C1—C6—H6119.6C26—C27—H27A107.4
C5—C6—H6119.6C28—C27—H27A107.4
C8—C7—C2179.3 (4)C26—C27—H27B107.4
C7—C8—C9177.7 (3)C28—C27—H27B107.4
O3—C9—C8110.1 (3)H27A—C27—H27B106.9
O3—C9—C11109.0 (3)C27—C28—H28A109.5
C8—C9—C11109.9 (3)C27—C28—H28B109.5
O3—C9—C10105.0 (3)H28A—C28—H28B109.5
C8—C9—C10110.8 (3)C27—C28—H28C109.5
C11—C9—C10111.9 (3)H28A—C28—H28C109.5
C9—C10—H10A109.5H28B—C28—H28C109.5
C9—C10—H10B109.5O2—C29—C30109.8 (2)
H10A—C10—H10B109.5O2—C29—H29A109.7
C9—C10—H10C109.5C30—C29—H29A109.7
H10A—C10—H10C109.5O2—C29—H29B109.7
H10B—C10—H10C109.5C30—C29—H29B109.7
C9—C11—H11A109.5H29A—C29—H29B108.2
C9—C11—H11B109.5C29—C30—C31113.0 (3)
H11A—C11—H11B109.5C29—C30—H30A109.0
C9—C11—H11C109.5C31—C30—H30A109.0
H11A—C11—H11C109.5C29—C30—H30B109.0
H11B—C11—H11C109.5C31—C30—H30B109.0
C13—C12—C5174.9 (3)H30A—C30—H30B107.8
C12—C13—C14177.3 (3)C32—C31—C30115.3 (3)
O4—C14—C13109.2 (3)C32—C31—H31A108.4
O4—C14—C16108.1 (3)C30—C31—H31A108.4
C13—C14—C16110.5 (3)C32—C31—H31B108.4
O4—C14—C15104.3 (3)C30—C31—H31B108.4
C13—C14—C15112.0 (3)H31A—C31—H31B107.5
C16—C14—C15112.5 (3)C33—C32—C31116.4 (3)
C14—C15—H15A109.5C33—C32—H32A108.2
C14—C15—H15B109.5C31—C32—H32A108.2
H15A—C15—H15B109.5C33—C32—H32B108.2
C14—C15—H15C109.5C31—C32—H32B108.2
H15A—C15—H15C109.5H32A—C32—H32B107.3
H15B—C15—H15C109.5C32—C33—C34116.5 (3)
C14—C16—H16A109.5C32—C33—H33A108.2
C14—C16—H16B109.5C34—C33—H33A108.2
H16A—C16—H16B109.5C32—C33—H33B108.2
C14—C16—H16C109.5C34—C33—H33B108.2
H16A—C16—H16C109.5H33A—C33—H33B107.3
H16B—C16—H16C109.5C35—C34—C33117.7 (3)
O1—C17—C18108.7 (2)C35—C34—H34A107.9
O1—C17—H17A109.9C33—C34—H34A107.9
C18—C17—H17A109.9C35—C34—H34B107.9
O1—C17—H17B109.9C33—C34—H34B107.9
C18—C17—H17B109.9H34A—C34—H34B107.2
H17A—C17—H17B108.3C36—C35—C34118.8 (3)
C17—C18—C19111.4 (2)C36—C35—H35A107.6
C17—C18—H18A109.4C34—C35—H35A107.6
C19—C18—H18A109.4C36—C35—H35B107.6
C17—C18—H18B109.4C34—C35—H35B107.6
C19—C18—H18B109.4H35A—C35—H35B107.1
H18A—C18—H18B108.0C37—C36—C35119.1 (3)
C20—C19—C18113.9 (3)C37—C36—H36A107.5
C20—C19—H19A108.8C35—C36—H36A107.5
C18—C19—H19A108.8C37—C36—H36B107.5
C20—C19—H19B108.8C35—C36—H36B107.5
C18—C19—H19B108.8H36A—C36—H36B107.0
H19A—C19—H19B107.7C36—C37—C38120.0 (4)
C19—C20—C21114.6 (3)C36—C37—H37A107.3
C19—C20—H20A108.6C38—C37—H37A107.3
C21—C20—H20A108.6C36—C37—H37B107.3
C19—C20—H20B108.6C38—C37—H37B107.3
C21—C20—H20B108.6H37A—C37—H37B106.9
H20A—C20—H20B107.6C39—C38—C37119.8 (4)
C20—C21—C22115.1 (3)C39—C38—H38A107.4
C20—C21—H21A108.5C37—C38—H38A107.4
C22—C21—H21A108.5C39—C38—H38B107.4
C20—C21—H21B108.5C37—C38—H38B107.4
C22—C21—H21B108.5H38A—C38—H38B106.9
H21A—C21—H21B107.5C38—C39—C40122.6 (4)
C23—C22—C21116.1 (3)C38—C39—H39A106.7
C23—C22—H22A108.3C40—C39—H39A106.7
C21—C22—H22A108.3C38—C39—H39B106.7
C23—C22—H22B108.3C40—C39—H39B106.7
C21—C22—H22B108.3H39A—C39—H39B106.6
H22A—C22—H22B107.4C39—C40—H40A109.5
C24—C23—C22117.0 (3)C39—C40—H40B109.5
C24—C23—H23A108.0H40A—C40—H40B109.5
C22—C23—H23A108.0C39—C40—H40C109.5
C24—C23—H23B108.0H40A—C40—H40C109.5
C22—C23—H23B108.0H40B—C40—H40C109.5
C17—O1—C1—C6−5.5 (4)C6—C5—C12—C13−36 (4)
C17—O1—C1—C2174.3 (3)C5—C12—C13—C1429 (11)
C6—C1—C2—C3−0.6 (4)C12—C13—C14—O4−73 (8)
O1—C1—C2—C3179.6 (3)C12—C13—C14—C1646 (8)
C6—C1—C2—C7−179.4 (3)C12—C13—C14—C15172 (8)
O1—C1—C2—C70.7 (4)C1—O1—C17—C18−177.2 (2)
C1—C2—C3—C4−0.2 (4)O1—C17—C18—C19176.3 (2)
C7—C2—C3—C4178.6 (3)C17—C18—C19—C20179.0 (3)
C2—C3—C4—O2−178.6 (3)C18—C19—C20—C21176.9 (3)
C2—C3—C4—C5−0.2 (4)C19—C20—C21—C22−179.8 (3)
C29—O2—C4—C32.0 (4)C20—C21—C22—C23178.8 (3)
C29—O2—C4—C5−176.4 (3)C21—C22—C23—C24−179.8 (3)
C3—C4—C5—C61.4 (4)C22—C23—C24—C25178.2 (4)
O2—C4—C5—C6179.9 (3)C23—C24—C25—C26179.6 (4)
C3—C4—C5—C12−176.6 (3)C24—C25—C26—C27178.7 (4)
O2—C4—C5—C122.0 (4)C25—C26—C27—C28179.8 (4)
O1—C1—C6—C5−178.4 (3)C4—O2—C29—C30177.6 (3)
C2—C1—C6—C51.8 (5)O2—C29—C30—C31−171.4 (3)
C4—C5—C6—C1−2.2 (4)C29—C30—C31—C32−176.5 (3)
C12—C5—C6—C1175.8 (3)C30—C31—C32—C33−177.8 (3)
C1—C2—C7—C8158 (29)C31—C32—C33—C34−179.5 (3)
C3—C2—C7—C8−20 (29)C32—C33—C34—C35−178.6 (3)
C2—C7—C8—C9−158 (24)C33—C34—C35—C36179.4 (4)
C7—C8—C9—O362 (9)C34—C35—C36—C37−178.6 (4)
C7—C8—C9—C11−58 (9)C35—C36—C37—C38−179.6 (4)
C7—C8—C9—C10178 (100)C36—C37—C38—C39−177.4 (4)
C4—C5—C12—C13141 (4)C37—C38—C39—C40−178.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O4i0.822.042.853 (3)173
O4—H4···O1i0.822.353.167 (3)175

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: VM2027).

References

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