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Acta Cryst. (2007). E63, o3954    [ doi:10.1107/S1600536807042304 ]

2,6-Bis[2-(4-benzyloxyphenyl)ethyl]biphenyl

S. C. Moratti, J. Simpson and S. M. Tierney

Abstract top

The title compound, C42H38O2, comprises a biphenyl system linked symmetrically at the 2- and 6-positions via two ethanediyl chains to two benzyloxyphenyl units. Both the ethanediyl and the benzyl ether linkages in the molecule are trans in the solid state, reinforcing the probability of a re-entrant structure. The rings of the biphenyl are inclined at 85.34 (8)° to one another. In the crystal structure, molecules form centrosymmetric dimers through C-H...O hydrogen bonds and are further linked into a three-dimensional network by a series of C-H...[pi] interactions.

Comment top

Auxetic materials are those with a negative Poisson ratio, i.e. they expand sideways upon stretching (Evans et al., 1991). A common theme in auxetic materials is that of the re-entrant structural motif. In this way, any force along one axis gets transmitted in a lateral fashion to a perpendicular axis. We were interested to see if such a unit could be deliberately designed into a polymer backbone. Computer simulations of such structures suggest that, under ideal situations, the resulting material should be auxetic (Evans et al., 1991; Aldred & Moratti, 2005). While rigid auxetic molecular structures are not too hard to design (Evans et al., 1991), ideally they should have some flexibility in order to accommodate chain motion and resultant strain.

By using a 1,2,3-trisubstituted phenyl ring and 1,2-ethane linkers it was hoped to get some flexibility as well as enforcing a re-entrant structure. In order to determine suitable polymer backbones, model oligomers were synthesized for structural analysis and monomer (I) was obtained from the hydrogenation of the Wittig-produced diene.

In (I), the biphenyl system is linked symmetrically at the 2 and 6-positions via two ethandiyl chains to two benzyloxyphenyl units. In the solid state, both the ethandiyl and benzyl ether linkages stayed trans - reinforcing the overall re-entrant structure of the central 1,2,3-phenyl linkage. The rings of the biphenyl group are almost orthogonal with a dihedral angle of 85.34 (8)° between them. The rings of the two benzyloxybenzene groups are inclined at 58.99 (10)° C1···C6/C9···C14 and 33.22 (13)° C31···C36/C39···C44 respectively.

In the crystal, molecules form inversion related dimers through C—H···O hydrogen bonds and are further linked into a three dimensional network by a series of C—H···π interactions. Fig 2, Table 1.

Related literature top

For information on auxetic materials, see: Evans et al. (1991); Aldred & Moratti (2005). No structures of benzyloxy ethyl benzene derivatives of biphenyl have been reported previously but two molecules with linked benzyloxybenzene systems are known; see Roesky et al. (1997); Cannon et al. (1989).

Experimental top

2,6-Bis(4-benzyloxystyryl)biphenyl, 1, (0.56 g, 1.0 mmol) and 10% palladium on charcoal (0.10 g, 0.1 mmol) in ethyl acetate (50 cm3) were rocked under hydrogen at 40 psi at room temperature for 48 h. The solution was filtered through a short celite pad and concentrated in vacuo to yield a yellow solid. Flash chromatography, eluting in hexane-ethyl acetate (4:1), afforded 2,6-bis[2-(4-benzyloxyphenyl)ethyl]biphenyl (0.23 g, 41%) as a white solid: mp 133–134 °C [Found: C, 87.3%; H, 6.65%; M+ 574.2872 (ESI). C42H38O2 requires C, 87.8%; H, 6.7%; M+ 574.2862]; νmax(KBr)/cm-1 3029 2956 2921 2865 (C—H), 1611 1582 1513 (aromatic), 1455, 1246, 1175, 1025; δH(400 MHz; CDCl3) 7.39 (10H, m, ArH), 7.35 (2H, m, ArH), 7.31 (2H, m, ArH), 7.16 (1H, s, ArH), 6.78 (8H, m, ArH), 5.00 (4H, s, CH2O), 2.59 (8H, m, CH2CH2); δC(101 MHz; CDCl3) 156.9, 141.4, 140.1, 139.8, 137.2, 134.4, 129.6, 129.2, 128.5, 128.1, 127.8, 127.4, 126.8, 114.6, 70.0 (OCH2), 37.0 (CH2CH2), 36.5 (CH2CH2). Colourless crystals of (I) were obtained as needles from ethyl acetate layered with hexane.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, Uiso=1.2Ueq (C) for aromatic and 0.99 Å, Uiso = 1.2Ueq (C) for CH2 groups. In the final difference Fourier map, two peaks of approximately 0.7 e Å−3 are found close to C7 and O8 but no chemical significance could be attached to them.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick 1997); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), enCIFer (Allen et al., 2004) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing the atom numbering with ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing for (I) with hydrogen bonds and C—H···π interactions drawn as dashed lines. Filled circles represent centroids of the benzene rings.
2,6-Bis[2-(4-benzyloxyphenyl)ethyl]biphenyl top
Crystal data top
C42H38O2Z = 2
Mr = 574.72F000 = 612
Triclinic, P1Dx = 1.183 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.0431 (3) ÅCell parameters from 12508 reflections
b = 10.2145 (3) Åθ = 1.0–27.5º
c = 16.4136 (5) ŵ = 0.07 mm−1
α = 100.213 (2)ºT = 180 (2) K
β = 98.218 (2)ºPlate, colourless
γ = 98.642 (2)º0.30 × 0.18 × 0.05 mm
V = 1613.22 (8) Å3
Data collection top
Nonius KappaCCD
diffractometer		7345 independent reflections
Radiation source: fine-focus sealed tube5114 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
T = 180(2) Kθmax = 27.5º
Thin–slice ω and φ scansθmin = 3.6º
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		h = −13→12
Tmin = 0.971, Tmax = 0.980k = −13→13
22105 measured reflectionsl = −20→21
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.169  w = 1/[σ2(Fo2) + (0.0633P)2 + 0.8567P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.005
7345 reflectionsΔρmax = 0.73 e Å−3
397 parametersΔρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C42H38O2γ = 98.642 (2)º
Mr = 574.72V = 1613.22 (8) Å3
Triclinic, P1Z = 2
a = 10.0431 (3) ÅMo Kα
b = 10.2145 (3) ŵ = 0.07 mm−1
c = 16.4136 (5) ÅT = 180 (2) K
α = 100.213 (2)º0.30 × 0.18 × 0.05 mm
β = 98.218 (2)º
Data collection top
Nonius KappaCCD
diffractometer		7345 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		5114 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.980Rint = 0.045
22105 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066397 parameters
wR(F2) = 0.169H-atom parameters constrained
S = 1.02Δρmax = 0.73 e Å−3
7345 reflectionsΔρmin = −0.44 e Å−3
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 > 2sigma(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
xyzUiso*/Ueq
C11.0625 (3)0.8508 (2)−0.04760 (14)0.0504 (6)
C20.9489 (2)0.8225 (2)−0.11049 (17)0.0565 (6)
H2A0.86180.7890−0.09850.068*
C30.9602 (3)0.8420 (2)−0.19012 (16)0.0593 (7)
H3A0.88110.8228−0.23260.071*
C41.0842 (3)0.8888 (3)−0.20805 (16)0.0618 (7)
H4A1.09180.9019−0.26320.074*
C51.1969 (3)0.9168 (3)−0.1476 (2)0.0681 (8)
H5A1.28340.9494−0.16060.082*
C61.1873 (3)0.8983 (3)−0.06724 (17)0.0610 (7)
H6A1.26710.9183−0.02520.073*
C71.0563 (3)0.8383 (3)0.04239 (17)0.0665 (7)
H7A1.14710.87400.07810.080*
H7B0.98960.89120.06450.080*
O81.0169 (2)0.70361 (19)0.04364 (12)0.0808 (6)
C90.9942 (3)0.6682 (3)0.11879 (15)0.0539 (6)
C101.0227 (2)0.7547 (2)0.19627 (16)0.0537 (6)
H10A1.06000.84750.20140.064*
C110.9958 (2)0.7036 (2)0.26760 (14)0.0468 (5)
H11A1.01560.76270.32120.056*
C120.94126 (19)0.5692 (2)0.26109 (12)0.0374 (4)
C130.9127 (3)0.4867 (2)0.18170 (14)0.0516 (6)
H13A0.87400.39400.17570.062*
C140.9387 (3)0.5350 (3)0.11136 (16)0.0634 (7)
H14A0.91820.47600.05780.076*
C150.91479 (19)0.5109 (2)0.33682 (13)0.0399 (5)
H15A0.97420.56910.38760.048*
H15B0.94040.42020.33040.048*
C160.76568 (18)0.49849 (19)0.34982 (11)0.0323 (4)
H16A0.74230.58990.36220.039*
H16B0.70490.44720.29740.039*
C170.74155 (16)0.42761 (18)0.42112 (11)0.0285 (4)
C180.74898 (16)0.49903 (17)0.50373 (11)0.0270 (4)
C190.73258 (17)0.42965 (18)0.56915 (11)0.0287 (4)
C200.70909 (18)0.28851 (19)0.55089 (12)0.0337 (4)
H20A0.69850.24050.59480.040*
C210.70094 (19)0.21757 (19)0.46983 (12)0.0359 (4)
H21A0.68460.12150.45830.043*
C220.71646 (18)0.28627 (19)0.40563 (12)0.0335 (4)
H22A0.71000.23680.35000.040*
C230.77486 (18)0.65079 (17)0.52238 (10)0.0286 (4)
C240.90739 (19)0.72428 (19)0.53862 (12)0.0355 (4)
H24A0.98250.67790.53690.043*
C250.9312 (2)0.8645 (2)0.55727 (13)0.0440 (5)
H25A1.02230.91350.56870.053*
C260.8231 (2)0.9328 (2)0.55932 (13)0.0481 (5)
H26A0.83941.02890.57230.058*
C270.6912 (2)0.8613 (2)0.54248 (13)0.0449 (5)
H27A0.61660.90840.54350.054*
C280.6665 (2)0.7211 (2)0.52408 (12)0.0368 (4)
H28A0.57510.67280.51260.044*
C290.73770 (18)0.50279 (19)0.65846 (11)0.0323 (4)
H29A0.79100.59530.66680.039*
H29B0.78570.45490.69770.039*
C300.5957 (2)0.5116 (2)0.67939 (12)0.0417 (5)
H30A0.54880.56140.64090.050*
H30B0.54180.41900.66940.050*
C310.59842 (19)0.5813 (2)0.76926 (12)0.0386 (4)
C320.5546 (2)0.7035 (2)0.78777 (13)0.0449 (5)
H32A0.52680.74720.74330.054*
C330.5504 (2)0.7636 (2)0.86958 (13)0.0477 (5)
H33A0.51870.84700.88070.057*
C340.5919 (2)0.7027 (2)0.93522 (13)0.0423 (5)
C350.6418 (2)0.5836 (2)0.91888 (14)0.0489 (5)
H35A0.67440.54280.96370.059*
C360.6437 (2)0.5239 (2)0.83581 (14)0.0461 (5)
H36A0.67700.44140.82470.055*
O370.57941 (18)0.76905 (16)1.01376 (9)0.0546 (4)
C380.6185 (2)0.7105 (2)1.08315 (13)0.0486 (5)
H38A0.71890.71591.09350.058*
H38B0.57460.61401.07140.058*
C390.5748 (2)0.7855 (2)1.15913 (13)0.0405 (5)
C400.4617 (3)0.8461 (3)1.15324 (16)0.0568 (6)
H40A0.40970.84321.09960.068*
C410.4231 (3)0.9115 (3)1.22520 (19)0.0696 (8)
H41A0.34470.95341.22100.084*
C420.4987 (3)0.9157 (3)1.30297 (18)0.0741 (8)
H42A0.47260.96041.35250.089*
C430.6112 (3)0.8553 (3)1.30865 (16)0.0708 (8)
H43A0.66350.85831.36220.085*
C440.6488 (3)0.7907 (2)1.23758 (14)0.0535 (6)
H44A0.72710.74881.24230.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0693 (15)0.0448 (12)0.0490 (13)0.0197 (11)0.0214 (11)0.0242 (10)
C20.0458 (13)0.0459 (13)0.0817 (18)0.0012 (10)0.0177 (12)0.0235 (12)
C30.0687 (16)0.0458 (13)0.0548 (15)0.0080 (12)−0.0095 (12)0.0059 (11)
C40.092 (2)0.0542 (15)0.0516 (14)0.0225 (14)0.0245 (14)0.0269 (12)
C50.0565 (15)0.0621 (16)0.098 (2)0.0035 (12)0.0314 (15)0.0411 (15)
C60.0521 (14)0.0575 (15)0.0701 (17)0.0041 (11)−0.0069 (12)0.0234 (13)
C70.0829 (19)0.0562 (15)0.0645 (16)0.0079 (14)0.0212 (14)0.0207 (13)
O80.1388 (19)0.0630 (12)0.0708 (12)0.0393 (12)0.0610 (13)0.0414 (10)
C90.0708 (16)0.0608 (15)0.0518 (14)0.0327 (12)0.0333 (12)0.0330 (12)
C100.0473 (13)0.0518 (13)0.0716 (16)0.0091 (10)0.0173 (11)0.0322 (12)
C110.0405 (11)0.0545 (13)0.0476 (12)0.0068 (10)0.0092 (9)0.0163 (10)
C120.0322 (10)0.0480 (11)0.0418 (11)0.0169 (8)0.0138 (8)0.0213 (9)
C130.0767 (16)0.0423 (12)0.0493 (13)0.0229 (11)0.0294 (12)0.0198 (10)
C140.110 (2)0.0508 (14)0.0480 (13)0.0344 (14)0.0382 (14)0.0226 (11)
C150.0328 (10)0.0563 (13)0.0385 (11)0.0140 (9)0.0107 (8)0.0224 (9)
C160.0294 (9)0.0399 (10)0.0297 (9)0.0095 (8)0.0054 (7)0.0098 (8)
C170.0217 (8)0.0338 (9)0.0318 (9)0.0079 (7)0.0051 (7)0.0088 (7)
C180.0208 (8)0.0294 (9)0.0317 (9)0.0052 (7)0.0044 (7)0.0084 (7)
C190.0220 (8)0.0338 (9)0.0317 (9)0.0055 (7)0.0049 (7)0.0097 (7)
C200.0313 (9)0.0340 (10)0.0387 (10)0.0050 (8)0.0075 (8)0.0147 (8)
C210.0345 (10)0.0277 (9)0.0451 (11)0.0053 (8)0.0042 (8)0.0083 (8)
C220.0313 (9)0.0349 (10)0.0329 (9)0.0074 (8)0.0048 (7)0.0024 (8)
C230.0316 (9)0.0305 (9)0.0249 (8)0.0062 (7)0.0046 (7)0.0082 (7)
C240.0336 (10)0.0355 (10)0.0386 (10)0.0047 (8)0.0044 (8)0.0138 (8)
C250.0468 (12)0.0362 (11)0.0445 (12)−0.0030 (9)−0.0012 (9)0.0128 (9)
C260.0694 (15)0.0280 (10)0.0433 (12)0.0065 (10)0.0016 (11)0.0066 (9)
C270.0549 (13)0.0388 (11)0.0450 (12)0.0197 (10)0.0102 (10)0.0086 (9)
C280.0352 (10)0.0382 (11)0.0394 (10)0.0111 (8)0.0088 (8)0.0085 (8)
C290.0296 (9)0.0377 (10)0.0304 (9)0.0041 (8)0.0055 (7)0.0105 (8)
C300.0323 (10)0.0532 (13)0.0378 (11)0.0060 (9)0.0075 (8)0.0044 (9)
C310.0298 (10)0.0466 (11)0.0383 (11)0.0021 (8)0.0090 (8)0.0074 (9)
C320.0419 (11)0.0568 (13)0.0374 (11)0.0141 (10)0.0052 (9)0.0100 (10)
C330.0524 (13)0.0510 (13)0.0414 (12)0.0172 (10)0.0088 (10)0.0064 (10)
C340.0450 (12)0.0455 (12)0.0365 (11)0.0059 (9)0.0148 (9)0.0040 (9)
C350.0620 (14)0.0513 (13)0.0409 (12)0.0156 (11)0.0190 (10)0.0167 (10)
C360.0543 (13)0.0420 (12)0.0476 (12)0.0129 (10)0.0211 (10)0.0108 (10)
O370.0773 (11)0.0561 (10)0.0343 (8)0.0223 (8)0.0144 (7)0.0073 (7)
C380.0509 (13)0.0589 (14)0.0421 (12)0.0187 (11)0.0142 (10)0.0139 (10)
C390.0440 (11)0.0396 (11)0.0388 (11)0.0039 (9)0.0134 (9)0.0088 (9)
C400.0518 (14)0.0674 (16)0.0504 (14)0.0153 (12)0.0079 (11)0.0069 (12)
C410.0597 (16)0.0670 (17)0.084 (2)0.0177 (13)0.0278 (15)0.0017 (15)
C420.095 (2)0.0669 (18)0.0559 (16)0.0004 (16)0.0405 (16)−0.0080 (13)
C430.097 (2)0.0713 (18)0.0383 (13)0.0064 (16)0.0100 (14)0.0059 (12)
C440.0592 (14)0.0558 (14)0.0474 (13)0.0101 (11)0.0089 (11)0.0163 (11)
Geometric parameters (Å, °) top
C1—C61.377 (3)C23—C241.390 (3)
C1—C21.382 (3)C23—C281.392 (2)
C1—C71.514 (3)C24—C251.387 (3)
C2—C31.375 (4)C24—H24A0.9500
C2—H2A0.9500C25—C261.378 (3)
C3—C41.357 (4)C25—H25A0.9500
C3—H3A0.9500C26—C271.377 (3)
C4—C51.352 (4)C26—H26A0.9500
C4—H4A0.9500C27—C281.386 (3)
C5—C61.380 (4)C27—H27A0.9500
C5—H5A0.9500C28—H28A0.9500
C6—H6A0.9500C29—C301.525 (3)
C7—O81.378 (3)C29—H29A0.9900
C7—H7A0.9900C29—H29B0.9900
C7—H7B0.9900C30—C311.515 (3)
O8—C91.385 (3)C30—H30A0.9900
C9—C141.368 (4)C30—H30B0.9900
C9—C101.379 (3)C31—C361.382 (3)
C10—C111.407 (3)C31—C321.384 (3)
C10—H10A0.9500C32—C331.383 (3)
C11—C121.379 (3)C32—H32A0.9500
C11—H11A0.9500C33—C341.381 (3)
C12—C131.386 (3)C33—H33A0.9500
C12—C151.510 (3)C34—O371.378 (2)
C13—C141.376 (3)C34—C351.381 (3)
C13—H13A0.9500C35—C361.396 (3)
C14—H14A0.9500C35—H35A0.9500
C15—C161.532 (3)C36—H36A0.9500
C15—H15A0.9900O37—C381.412 (3)
C15—H15B0.9900C38—C391.501 (3)
C16—C171.510 (2)C38—H38A0.9900
C16—H16A0.9900C38—H38B0.9900
C16—H16B0.9900C39—C401.373 (3)
C17—C221.398 (2)C39—C441.380 (3)
C17—C181.407 (2)C40—C411.386 (4)
C18—C191.403 (2)C40—H40A0.9500
C18—C231.501 (2)C41—C421.379 (4)
C19—C201.396 (2)C41—H41A0.9500
C19—C291.513 (2)C42—C431.366 (4)
C20—C211.382 (3)C42—H42A0.9500
C20—H20A0.9500C43—C441.367 (4)
C21—C221.380 (3)C43—H43A0.9500
C21—H21A0.9500C44—H44A0.9500
C22—H22A0.9500
C6—C1—C2118.1 (2)C24—C23—C28118.52 (17)
C6—C1—C7118.3 (2)C24—C23—C18120.83 (16)
C2—C1—C7123.6 (2)C28—C23—C18120.64 (16)
C3—C2—C1120.8 (2)C25—C24—C23120.76 (18)
C3—C2—H2A119.6C25—C24—H24A119.6
C1—C2—H2A119.6C23—C24—H24A119.6
C4—C3—C2120.1 (2)C26—C25—C24120.11 (19)
C4—C3—H3A120.0C26—C25—H25A119.9
C2—C3—H3A120.0C24—C25—H25A119.9
C5—C4—C3120.1 (2)C27—C26—C25119.73 (19)
C5—C4—H4A119.9C27—C26—H26A120.1
C3—C4—H4A119.9C25—C26—H26A120.1
C4—C5—C6120.5 (2)C26—C27—C28120.54 (19)
C4—C5—H5A119.7C26—C27—H27A119.7
C6—C5—H5A119.7C28—C27—H27A119.7
C1—C6—C5120.3 (2)C27—C28—C23120.33 (19)
C1—C6—H6A119.8C27—C28—H28A119.8
C5—C6—H6A119.8C23—C28—H28A119.8
O8—C7—C1108.3 (2)C19—C29—C30112.53 (15)
O8—C7—H7A110.0C19—C29—H29A109.1
C1—C7—H7A110.0C30—C29—H29A109.1
O8—C7—H7B110.0C19—C29—H29B109.1
C1—C7—H7B110.0C30—C29—H29B109.1
H7A—C7—H7B108.4H29A—C29—H29B107.8
C7—O8—C9118.7 (2)C31—C30—C29113.37 (16)
C14—C9—C10120.3 (2)C31—C30—H30A108.9
C14—C9—O8114.2 (2)C29—C30—H30A108.9
C10—C9—O8125.5 (2)C31—C30—H30B108.9
C9—C10—C11119.1 (2)C29—C30—H30B108.9
C9—C10—H10A120.4H30A—C30—H30B107.7
C11—C10—H10A120.4C36—C31—C32117.61 (19)
C12—C11—C10121.1 (2)C36—C31—C30120.93 (19)
C12—C11—H11A119.4C32—C31—C30121.46 (19)
C10—C11—H11A119.4C33—C32—C31121.4 (2)
C11—C12—C13117.58 (19)C33—C32—H32A119.3
C11—C12—C15122.25 (19)C31—C32—H32A119.3
C13—C12—C15120.16 (19)C34—C33—C32120.2 (2)
C14—C13—C12122.0 (2)C34—C33—H33A119.9
C14—C13—H13A119.0C32—C33—H33A119.9
C12—C13—H13A119.0O37—C34—C35125.08 (19)
C9—C14—C13119.8 (2)O37—C34—C33115.36 (19)
C9—C14—H14A120.1C35—C34—C33119.56 (19)
C13—C14—H14A120.1C34—C35—C36119.3 (2)
C12—C15—C16113.56 (15)C34—C35—H35A120.4
C12—C15—H15A108.9C36—C35—H35A120.4
C16—C15—H15A108.9C31—C36—C35121.8 (2)
C12—C15—H15B108.9C31—C36—H36A119.1
C16—C15—H15B108.9C35—C36—H36A119.1
H15A—C15—H15B107.7C34—O37—C38117.91 (17)
C17—C16—C15111.51 (14)O37—C38—C39108.87 (17)
C17—C16—H16A109.3O37—C38—H38A109.9
C15—C16—H16A109.3C39—C38—H38A109.9
C17—C16—H16B109.3O37—C38—H38B109.9
C15—C16—H16B109.3C39—C38—H38B109.9
H16A—C16—H16B108.0H38A—C38—H38B108.3
C22—C17—C18118.59 (16)C40—C39—C44119.0 (2)
C22—C17—C16119.16 (16)C40—C39—C38122.1 (2)
C18—C17—C16122.20 (16)C44—C39—C38118.9 (2)
C19—C18—C17120.59 (16)C39—C40—C41120.2 (2)
C19—C18—C23119.48 (15)C39—C40—H40A119.9
C17—C18—C23119.92 (15)C41—C40—H40A119.9
C20—C19—C18118.82 (16)C42—C41—C40119.8 (3)
C20—C19—C29119.04 (16)C42—C41—H41A120.1
C18—C19—C29122.13 (16)C40—C41—H41A120.1
C21—C20—C19120.95 (17)C43—C42—C41119.8 (2)
C21—C20—H20A119.5C43—C42—H42A120.1
C19—C20—H20A119.5C41—C42—H42A120.1
C22—C21—C20120.01 (17)C42—C43—C44120.2 (3)
C22—C21—H21A120.0C42—C43—H43A119.9
C20—C21—H21A120.0C44—C43—H43A119.9
C21—C22—C17121.04 (17)C43—C44—C39120.9 (2)
C21—C22—H22A119.5C43—C44—H44A119.5
C17—C22—H22A119.5C39—C44—H44A119.5
C6—C1—C2—C3−0.4 (4)C16—C17—C22—C21176.61 (16)
C7—C1—C2—C3176.8 (2)C19—C18—C23—C2494.7 (2)
C1—C2—C3—C40.5 (4)C17—C18—C23—C24−85.2 (2)
C2—C3—C4—C5−0.2 (4)C19—C18—C23—C28−85.1 (2)
C3—C4—C5—C60.0 (4)C17—C18—C23—C2895.0 (2)
C2—C1—C6—C50.2 (4)C28—C23—C24—C250.9 (3)
C7—C1—C6—C5−177.2 (2)C18—C23—C24—C25−178.87 (17)
C4—C5—C6—C10.1 (4)C23—C24—C25—C26−0.5 (3)
C6—C1—C7—O8−116.2 (3)C24—C25—C26—C27−0.2 (3)
C2—C1—C7—O866.5 (3)C25—C26—C27—C280.5 (3)
C1—C7—O8—C9−175.3 (2)C26—C27—C28—C230.0 (3)
C7—O8—C9—C14171.9 (2)C24—C23—C28—C27−0.7 (3)
C7—O8—C9—C10−8.0 (4)C18—C23—C28—C27179.12 (17)
C14—C9—C10—C111.0 (4)C20—C19—C29—C30−82.1 (2)
O8—C9—C10—C11−179.1 (2)C18—C19—C29—C3097.1 (2)
C9—C10—C11—C12−0.3 (3)C19—C29—C30—C31178.50 (17)
C10—C11—C12—C13−0.6 (3)C29—C30—C31—C36−66.3 (3)
C10—C11—C12—C15178.38 (19)C29—C30—C31—C32114.4 (2)
C11—C12—C13—C140.8 (3)C36—C31—C32—C33−2.8 (3)
C15—C12—C13—C14−178.2 (2)C30—C31—C32—C33176.6 (2)
C10—C9—C14—C13−0.8 (4)C31—C32—C33—C340.8 (3)
O8—C9—C14—C13179.3 (2)C32—C33—C34—O37−178.05 (19)
C12—C13—C14—C9−0.1 (4)C32—C33—C34—C352.0 (3)
C11—C12—C15—C1698.6 (2)O37—C34—C35—C36177.3 (2)
C13—C12—C15—C16−82.4 (2)C33—C34—C35—C36−2.7 (3)
C12—C15—C16—C17174.56 (17)C32—C31—C36—C352.0 (3)
C15—C16—C17—C22−83.3 (2)C30—C31—C36—C35−177.3 (2)
C15—C16—C17—C1894.1 (2)C34—C35—C36—C310.7 (3)
C22—C17—C18—C190.5 (2)C35—C34—O37—C38−0.9 (3)
C16—C17—C18—C19−176.86 (15)C33—C34—O37—C38179.1 (2)
C22—C17—C18—C23−179.60 (15)C34—O37—C38—C39−170.58 (18)
C16—C17—C18—C233.1 (2)O37—C38—C39—C4030.2 (3)
C17—C18—C19—C200.2 (2)O37—C38—C39—C44−151.5 (2)
C23—C18—C19—C20−179.76 (15)C44—C39—C40—C410.1 (4)
C17—C18—C19—C29−179.03 (15)C38—C39—C40—C41178.4 (2)
C23—C18—C19—C291.1 (2)C39—C40—C41—C420.0 (4)
C18—C19—C20—C21−0.5 (3)C40—C41—C42—C430.0 (4)
C29—C19—C20—C21178.72 (16)C41—C42—C43—C44−0.1 (4)
C19—C20—C21—C220.2 (3)C42—C43—C44—C390.2 (4)
C20—C21—C22—C170.5 (3)C40—C39—C44—C43−0.2 (4)
C18—C17—C22—C21−0.8 (3)C38—C39—C44—C43−178.6 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O8i0.952.483.326 (4)149
C2—H2A···Cg5ii0.952.783.644 (2)152
C7—H7B···Cg1iii0.992.683.575 (3)150
C13—H13A···Cg1iv0.952.823.620 (2)143
C28—H28A···Cg3v0.952.983.865 (2)155
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, y, z+1; (iii) −x, −y, −z+2; (iv) −x, −y+1, −z+2; (v) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O8i0.952.483.326 (4)149
C2—H2A···Cg5ii0.952.783.644 (2)152
C7—H7B···Cg1iii0.992.683.575 (3)150
C13—H13A···Cg1iv0.952.823.620 (2)143
C28—H28A···Cg3v0.952.983.865 (2)155
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, y, z+1; (iii) −x, −y, −z+2; (iv) −x, −y+1, −z+2; (v) −x+1, −y+1, −z+1.
Acknowledgements top

We thank Dr John Davies, University of Cambridge, for the X-ray data collection.

references
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