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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...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042304/ng2317sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042304/ng2317Isup2.hkl
Contains datablock I

CCDC reference: 663686

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.066
  • wR factor = 0.169
  • Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C1 - C7 .. 8.78 su
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.730 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.73 e/A    PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.37 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O8
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

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.

Structure description 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.

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).

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 = 574.72F(000) = 612
Triclinic, P1Dx = 1.183 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0431 (3) ÅCell parameters from 12508 reflections
b = 10.2145 (3) Åθ = 1.0–27.5°
c = 16.4136 (5) ŵ = 0.07 mm1
α = 100.213 (2)°T = 180 K
β = 98.218 (2)°Plate, colourless
γ = 98.642 (2)°0.30 × 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)
Graphite monochromatorRint = 0.045
Thin–slice ω and φ scansθmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1312
Tmin = 0.971, Tmax = 0.980k = 1313
22105 measured reflectionsl = 2021
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0633P)2 + 0.8567P]
where P = (Fo2 + 2Fc2)/3
7345 reflections(Δ/σ)max = 0.005
397 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C42H38O2γ = 98.642 (2)°
Mr = 574.72V = 1613.22 (8) Å3
Triclinic, P1Z = 2
a = 10.0431 (3) ÅMo Kα radiation
b = 10.2145 (3) ŵ = 0.07 mm1
c = 16.4136 (5) ÅT = 180 K
α = 100.213 (2)°0.30 × 0.18 × 0.05 mm
β = 98.218 (2)°
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)] = 0.0660 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 1.02Δρmax = 0.73 e Å3
7345 reflectionsΔρmin = 0.44 e Å3
397 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
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)
H2A0.86180.78900.09850.068*
C30.9602 (3)0.8420 (2)0.19012 (16)0.0593 (7)
H3A0.88110.82280.23260.071*
C41.0842 (3)0.8888 (3)0.20805 (16)0.0618 (7)
H4A1.09180.90190.26320.074*
C51.1969 (3)0.9168 (3)0.1476 (2)0.0681 (8)
H5A1.28340.94940.16060.082*
C61.1873 (3)0.8983 (3)0.06724 (17)0.0610 (7)
H6A1.26710.91830.02520.073*
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, º) 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—C30.4 (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—C2485.2 (2)
C2—C3—C4—C50.2 (4)C19—C18—C23—C2885.1 (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—C5177.2 (2)C18—C23—C24—C25178.87 (17)
C4—C5—C6—C10.1 (4)C23—C24—C25—C260.5 (3)
C6—C1—C7—O8116.2 (3)C24—C25—C26—C270.2 (3)
C2—C1—C7—O866.5 (3)C25—C26—C27—C280.5 (3)
C1—C7—O8—C9175.3 (2)C26—C27—C28—C230.0 (3)
C7—O8—C9—C14171.9 (2)C24—C23—C28—C270.7 (3)
C7—O8—C9—C108.0 (4)C18—C23—C28—C27179.12 (17)
C14—C9—C10—C111.0 (4)C20—C19—C29—C3082.1 (2)
O8—C9—C10—C11179.1 (2)C18—C19—C29—C3097.1 (2)
C9—C10—C11—C120.3 (3)C19—C29—C30—C31178.50 (17)
C10—C11—C12—C130.6 (3)C29—C30—C31—C3666.3 (3)
C10—C11—C12—C15178.38 (19)C29—C30—C31—C32114.4 (2)
C11—C12—C13—C140.8 (3)C36—C31—C32—C332.8 (3)
C15—C12—C13—C14178.2 (2)C30—C31—C32—C33176.6 (2)
C10—C9—C14—C130.8 (4)C31—C32—C33—C340.8 (3)
O8—C9—C14—C13179.3 (2)C32—C33—C34—O37178.05 (19)
C12—C13—C14—C90.1 (4)C32—C33—C34—C352.0 (3)
C11—C12—C15—C1698.6 (2)O37—C34—C35—C36177.3 (2)
C13—C12—C15—C1682.4 (2)C33—C34—C35—C362.7 (3)
C12—C15—C16—C17174.56 (17)C32—C31—C36—C352.0 (3)
C15—C16—C17—C2283.3 (2)C30—C31—C36—C35177.3 (2)
C15—C16—C17—C1894.1 (2)C34—C35—C36—C310.7 (3)
C22—C17—C18—C190.5 (2)C35—C34—O37—C380.9 (3)
C16—C17—C18—C19176.86 (15)C33—C34—O37—C38179.1 (2)
C22—C17—C18—C23179.60 (15)C34—O37—C38—C39170.58 (18)
C16—C17—C18—C233.1 (2)O37—C38—C39—C4030.2 (3)
C17—C18—C19—C200.2 (2)O37—C38—C39—C44151.5 (2)
C23—C18—C19—C20179.76 (15)C44—C39—C40—C410.1 (4)
C17—C18—C19—C29179.03 (15)C38—C39—C40—C41178.4 (2)
C23—C18—C19—C291.1 (2)C39—C40—C41—C420.0 (4)
C18—C19—C20—C210.5 (3)C40—C41—C42—C430.0 (4)
C29—C19—C20—C21178.72 (16)C41—C42—C43—C440.1 (4)
C19—C20—C21—C220.2 (3)C42—C43—C44—C390.2 (4)
C20—C21—C22—C170.5 (3)C40—C39—C44—C430.2 (4)
C18—C17—C22—C210.8 (3)C38—C39—C44—C43178.6 (2)
Hydrogen-bond geometry (Å, º) 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.

Experimental details

Crystal data
Chemical formulaC42H38O2
Mr574.72
Crystal system, space groupTriclinic, P1
Temperature (K)180
a, b, c (Å)10.0431 (3), 10.2145 (3), 16.4136 (5)
α, β, γ (°)100.213 (2), 98.218 (2), 98.642 (2)
V3)1613.22 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.18 × 0.05
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.971, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
22105, 7345, 5114
Rint0.045
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.169, 1.02
No. of reflections7345
No. of parameters397
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.73, 0.44

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick 1997), SHELXL97 (Sheldrick 1997), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 1997), enCIFer (Allen et al., 2004) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O8i0.952.483.326 (4)148.5
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.
 

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