The title 2,6-disubstituted pyridine, C41H61NO4, with a crystallographic twofold axis, has an arrangement of mol­ecules well organized to undergo multiple cyclo­metallation reactions

Alcock, N. W.

Rourke, J. P.

Online Research @ Cardiff

organic paperso368 Alcock and Rourke  C41H61NO4 doi:10.1107/S1600536805001248 Acta Cryst. (2005). E61, o368±o369Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-53682,6-Bis[2,4-bis(heptyloxy)phenyl]pyridineNathaniel W. Alcock* andJonathan P RourkeDepartment of Chemistry, University ofWarwick, Coventry CV4 7AL, EnglandCorrespondence e-mail:n.w.alcock@warwick.ac.ukKey indicatorsSingle-crystal X-ray studyT = 180 KMean (C±C) = 0.004 AÊDisorder in main residueR factor = 0.060wR factor = 0.168Data-to-parameter ratio = 14.5For details of how these key indicators wereautomatically derived from the article, seehttp://journals.iucr.org/e.# 2005 International Union of CrystallographyPrinted in Great Britain ± all rights reservedThe title 2,6-disubstituted pyridine, C41H61NO4, with acrystallographic twofold axis, has an arrangement of moleculeswell organized to undergo multiple cyclometallation reactions.Comment2,6-Disubstituted pyridines are ideally set up to undergomultiple cyclometallations, reactions of considerable interestto us (Cave et al., 1999, 2000). In addition to their ability toundergo multiple cyclometallations, such compounds havealso been shown to be activated by other reagents (Cave et al.,1998).The title molecule, (I) (Fig. 1), has crystallographic twofoldsymmetry and the aliphatic chains are each in an extendedform. Within the unit cell, the molecules are aligned in anantiparallel fashion (Figs. 2 and 3).Experimental1-Chloro-2,4-bis(heptyloxy)benzene (15.0 g, 48.0 mmol) was addeddropwise to a stirred solution of magnesium (1.22 g, 50.0 mmol) andmethyl iodide (0.30 g, 2.11 mmol) in tetrahydrofuran (THF, 25 ml)under an inert atmosphere. The resulting Grignard reagent wastransferred via a cannula to a stirred solution of 2,6-dichloropyridine(2.96 g, 20.0 mmol) and tetrakis(triphenylphosphine)palladium(0.45 g, 0.50 mmol) in THF (25 ml). The reaction mixture was thenheated under re¯ux (24 h) under an inert atmosphere. ExcessGrignard was destroyed with water (20 ml) and hydrochloric acid(5 ml, 2 M). The neutralized (aqueous NaOH) reaction mixture wasextracted with diethyl ether (2  200 ml) and dried (saturated NaCland magnesium sulfate). The solvent was removed under vacuum andthe product crystallized out as white needle-like crystals (yield: 12.0 g,19.0 mmol, 95%). 1H NMR (CDCl3, 250.13 MHz):  7.96 (2H, d,3J =8.5 Hz), 7.75 (2H, d, 3J = 7.3 Hz), 7.60 (1H, t, 3J = 7.3 Hz), 6.59 (2H,dd, 3J = 8.5, 4J = 2.1 Hz), 6.53 (2H, d, 4J = 2.1 Hz), 3.99 (8H, t, 3J =6.7 Hz), 1.79 (8H, m), 1.48 (24H, m), 0.89 (12H, m). 13C NMR(CDCl3, 250.13 MHz):  160.5, 157.7, 154.7, 134.8, 132.1, 131.5, 121.9,105.6, 100.0, 68.2, 31.4, 25.7, 22.5. Elemental analysis found(expected): C 77.8 (77.9), H 9.6 (9.7), N 2.4% (2.2%).Received 16 December 2004Accepted 13 January 2005Online 22 January 2005Crystal dataC41H61NO4Mr = 631.91Monoclinic, P2=na = 11.2502 (10) AÊb = 6.9682 (6) AÊc = 24.014 (2) AÊ = 93.963 (2)V = 1878.0 (3) AÊ 3Z = 2Dx = 1.117 Mg mÿ3Mo K radiationCell parameters from 2201re¯ections = 3±15 = 0.07 mmÿ1T = 180 (2) KBlock, colourless0.45  0.25  0.20 mmData collectionBruker SMART diffractometer! scansAbsorption correction: multi-scan(SADABS; Sheldrick, 1996)Tmin = 0.896, Tmax = 0.9898996 measured re¯ections3318 independent re¯ections1753 re¯ections with I > 2(I)Rint = 0.045max = 25.0h = ÿ13! 13k = ÿ8! 7l = ÿ18! 28RefinementRe®nement on F 2R[F 2 > 2(F 2)] = 0.060wR(F 2) = 0.168S = 1.043318 re¯ections229 parametersH-atom parameters constrainedw = 1/[2(Fo2) + (0.078P)2]where P = (Fo2 + 2Fc2)/3(/)max = 0.043max = 0.21 e AÊÿ3min = ÿ0.22 e AÊ ÿ3H atoms were added at calculated positions (CÐH = 0.95±0.99 AÊ )and re®ned using a riding model (including free rotation about CÐCbonds for methyl groups), with Uiso(H) = 1.2 (or 1.5 for methyl Hatoms) times Ueq(C). The terminal section of one of the heptanechains was found to be disordered between two positions [relativeoccupancies 0.43 (1):0.57 (1)]. This disorder is believed to beresponsible for various anomalies in the displacement parameters ofthe atoms in this region of the molecule.Data collection: SMART (Siemens, 1994); cell re®nement: SAINT(Siemens, 1995); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 1997a); program(s) used to re®nestructure: SHELXL97 (Sheldrick, 1997a); molecular graphics:SHELXTL (Sheldrick, 1997b); software used to prepare material forpublication: SHELXTL.The EPSRC and Siemens generously supported thepurchase of the SMART diffractometer.ReferencesCave, G. W. V., Alcock, N. W. & Rourke, J. P. (1999). Organometallics, 18,1801±1803.Cave, G. W. V., Fanizzi, F. P., Deeth, R. J., Errington, W. & Rourke, J. P. (2000).Organometallics, 19, 1355±1364.Cave, G. W. V., Hallett, A. J., Errington, W. & Rourke, J. P. (1998). Angew.Chem. Int. Ed. 37, 3270±3272.Sheldrick, G. M. (1996). SADABS. University of GoÈ ttingen, Germany.Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University ofGoÈ ttingen, Germany.Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison,Wisconsin, USA.Siemens (1994). SMART. Siemens Analytical X-ray Instruments Inc.,Madison, Wisconsin, USA.Siemens (1995). SAINT. Version 4. Siemens Analytical X-ray InstrumentsInc., Madison, Wisconsin, USA.organic papersActa Cryst. (2005). E61, o368±o369 Alcock and Rourke  C41H61NO4 o369Figure 1View of the title molecule, showing the atomic numbering. Displacementellipsoids are drawn at the 50% probability level. Both disordercomponents are shown in all Figures.Figure 2Packing diagram of (I), viewed down the a axis. H atoms have beenomitted.Figure 3Packing diagram of (I), viewed down the b axis. H atoms have beenomitted.supporting informationsup-1Acta Cryst. (2005). E61, o368–o369    supporting informationActa Cryst. (2005). E61, o368–o369    [https://doi.org/10.1107/S1600536805001248]2,6-Bis[2,4-bis(heptyloxy)phenyl]pyridineNathaniel W. Alcock and Jonathan P Rourke2,6-Bis[2,4-bis(heptyloxy)phenyl]pyridine Crystal data C41H61NO4Mr = 631.91Monoclinic, P2/nHall symbol: -P 2yaca = 11.2502 (10) Åb = 6.9682 (6) Åc = 24.014 (2) Åβ = 93.963 (2)°V = 1878.0 (3) Å3Z = 2F(000) = 692Dx = 1.117 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 2201 reflectionsθ = 3–15°µ = 0.07 mm−1T = 180 KBlock, colourless0.45 × 0.25 × 0.2 mmData collection Siemens SMART diffractometerRadiation source: fine-focus sealed tubeGraphite monochromatorDetector resolution: 8.192 pixels mm-1ω scansAbsorption correction: multi-scan (SADABS; Sheldrick, 1996)Tmin = 0.896, Tmax = 0.9898996 measured reflections3318 independent reflections1753 reflections with I > 2σ(I)Rint = 0.045θmax = 25.0°, θmin = 1.7°h = −13→13k = −8→7l = −18→28Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.060wR(F2) = 0.168S = 1.043318 reflections229 parameters2 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: inferred from neighbouring sitesH-atom parameters constrainedw = 1/[σ2(Fo2) + (0.078P)2] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.043Δρmax = 0.21 e Å−3Δρmin = −0.22 e Å−3supporting informationsup-2Acta Cryst. (2005). E61, o368–o369    Special details Experimental. The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cooler (Cosier & Glazer, 1986). The data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures with different φ angles for the crystal; each 10 s exposure covered 0.3° in ω. The crystal-to-detector distance was 5.0 cm. Coverage of the unique set is over 97% complete to at least 26° in θ. Crystal decay was found to be negligible by by repeating the initial frames at data collection and analyzing the duplicate reflections.Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for methyl atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached.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) x y z Uiso*/Ueq Occ. (<1)O1 0.27150 (17) 0.9445 (3) 0.49155 (7) 0.0557 (6)O2 0.12875 (16) 0.3876 (2) 0.39451 (7) 0.0541 (6)C01 0.2706 (2) 0.8380 (4) 0.44357 (10) 0.0443 (7)C02 0.2012 (2) 0.6730 (4) 0.44313 (10) 0.0451 (7)H02A 0.1582 0.6425 0.4746 0.054*C03 0.1942 (2) 0.5526 (4) 0.39711 (10) 0.0422 (7)C04 0.2560 (2) 0.5969 (3) 0.34979 (9) 0.0366 (6)C05 0.3235 (2) 0.7629 (4) 0.35173 (10) 0.0413 (7)H05A 0.3653 0.7958 0.3200 0.050*C06 0.3333 (2) 0.8842 (4) 0.39782 (10) 0.0437 (7)H06A 0.3818 0.9958 0.3979 0.052*C07 0.2497 (2) 0.4772 (4) 0.29833 (10) 0.0372 (6)N08 0.2500 0.5760 (4) 0.2500 0.0376 (7)C009 0.2482 (2) 0.2775 (4) 0.29932 (11) 0.0435 (7)H09A 0.2460 0.2110 0.3338 0.052*C010 0.2500 0.1771 (5) 0.2500 0.0430 (9)H01C 0.2500 0.0408 0.2500 0.052*C11 0.3361 (2) 1.1221 (4) 0.49299 (10) 0.0492 (7)H11A 0.3040 1.2079 0.4627 0.059*H11B 0.4214 1.0980 0.4877 0.059*C12 0.3225 (3) 1.2141 (4) 0.54911 (10) 0.0535 (8)H12A 0.3514 1.1239 0.5789 0.064*H12B 0.2371 1.2390 0.5535 0.064*C13 0.3912 (2) 1.4015 (4) 0.55598 (11) 0.0490 (7)H13A 0.4766 1.3763 0.5515 0.059*H13B 0.3623 1.4913 0.5261 0.059*C14 0.3784 (2) 1.4954 (4) 0.61216 (11) 0.0540 (8)H14A 0.2927 1.5150 0.6172 0.065*supporting informationsup-3Acta Cryst. (2005). E61, o368–o369    H14B 0.4102 1.4071 0.6419 0.065*C15 0.4417 (3) 1.6856 (4) 0.61915 (12) 0.0585 (8)H15A 0.4093 1.7744 0.5897 0.070*H15B 0.5273 1.6663 0.6136 0.070*C16 0.4301 (3) 1.7785 (5) 0.67574 (13) 0.0759 (10)H16A 0.4709 1.9028 0.6769 0.114*H16B 0.4663 1.6951 0.7051 0.114*H16C 0.3456 1.7975 0.6817 0.114*C21 0.0420 (3) 0.3509 (4) 0.43410 (13) 0.0642 (9)H21A −0.0202 0.4517 0.4321 0.077*H21B 0.0800 0.3472 0.4725 0.077*C22 −0.0114 (4) 0.1576 (5) 0.41802 (17) 0.0954 (14)H22A 0.0528 0.0602 0.4208 0.114*H22B −0.0697 0.1228 0.4454 0.114*C23 −0.0705 (4) 0.1487 (7) 0.3625 (2) 0.145 (2)H23A −0.0256 0.2193 0.3350 0.174* 0.554 (17)H23B −0.1530 0.1988 0.3618 0.174* 0.554 (17)H23C −0.0142 0.2079 0.3376 0.174* 0.446 (17)H23D −0.1383 0.2389 0.3635 0.174* 0.446 (17)C24A −0.0681 (14) −0.0784 (13) 0.3520 (6) 0.112 (6) 0.554 (17)H24A 0.0098 −0.1248 0.3684 0.134* 0.554 (17)H24B −0.1295 −0.1346 0.3747 0.134* 0.554 (17)C25A −0.083 (2) −0.152 (2) 0.3054 (8) 0.181 (8) 0.554 (17)H25A −0.0297 −0.0728 0.2833 0.218* 0.554 (17)H25B −0.1643 −0.1095 0.2931 0.218* 0.554 (17)C24B −0.1284 (9) −0.0165 (13) 0.3271 (5) 0.070 (4) 0.446 (17)H24C −0.1757 0.0331 0.2939 0.084* 0.446 (17)H24D −0.1801 −0.0969 0.3494 0.084* 0.446 (17)C25B −0.0166 (9) −0.130 (2) 0.3104 (5) 0.066 (4) 0.446 (17)H25C 0.0368 −0.1626 0.3435 0.079* 0.446 (17)H25D 0.0287 −0.0562 0.2837 0.079* 0.446 (17)C26 −0.0762 (4) −0.3254 (7) 0.28082 (17) 0.1204 (16)H26A −0.1069 −0.3160 0.2417 0.181* 0.554 (17)H26B −0.1240 −0.4180 0.3003 0.181* 0.554 (17)H26C 0.0070 −0.3682 0.2826 0.181* 0.554 (17)H26D −0.0117 −0.4042 0.2676 0.181* 0.446 (17)H26E −0.1300 −0.2868 0.2490 0.181* 0.446 (17)H26F −0.1206 −0.3997 0.3071 0.181* 0.446 (17)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23O1 0.0802 (15) 0.0520 (13) 0.0360 (11) −0.0067 (10) 0.0114 (10) −0.0088 (9)O2 0.0646 (13) 0.0517 (12) 0.0484 (12) −0.0118 (10) 0.0215 (9) −0.0057 (10)C01 0.0566 (18) 0.0463 (17) 0.0298 (15) 0.0079 (14) 0.0023 (13) −0.0010 (13)C02 0.0545 (18) 0.0496 (18) 0.0325 (16) 0.0021 (14) 0.0121 (12) 0.0044 (13)C03 0.0490 (17) 0.0400 (16) 0.0381 (16) 0.0025 (13) 0.0069 (12) 0.0017 (13)C04 0.0443 (15) 0.0355 (15) 0.0300 (14) 0.0073 (12) 0.0027 (11) 0.0010 (12)supporting informationsup-4Acta Cryst. (2005). E61, o368–o369    C05 0.0516 (17) 0.0407 (16) 0.0320 (15) 0.0033 (13) 0.0068 (12) 0.0039 (12)C06 0.0567 (18) 0.0376 (15) 0.0367 (16) 0.0009 (13) 0.0034 (13) 0.0012 (13)C07 0.0373 (15) 0.0392 (16) 0.0355 (15) 0.0032 (12) 0.0062 (12) 0.0023 (12)N08 0.0451 (18) 0.0372 (18) 0.0307 (17) 0.000 0.0040 (13) 0.000C009 0.0495 (17) 0.0416 (17) 0.0400 (16) 0.0034 (13) 0.0071 (12) 0.0048 (13)C010 0.051 (2) 0.032 (2) 0.046 (2) 0.000 0.0066 (18) 0.000C11 0.0569 (18) 0.0506 (18) 0.0400 (16) 0.0015 (14) 0.0017 (13) −0.0064 (14)C12 0.066 (2) 0.0540 (19) 0.0406 (17) −0.0002 (15) 0.0045 (14) −0.0038 (14)C13 0.0570 (18) 0.0502 (18) 0.0398 (16) 0.0056 (14) 0.0023 (13) −0.0041 (14)C14 0.0570 (19) 0.0567 (19) 0.0489 (18) −0.0020 (15) 0.0077 (14) −0.0110 (15)C15 0.063 (2) 0.0550 (19) 0.057 (2) 0.0009 (15) −0.0013 (15) −0.0082 (15)C16 0.072 (2) 0.080 (2) 0.076 (2) −0.0088 (18) 0.0062 (18) −0.0286 (19)C21 0.067 (2) 0.066 (2) 0.063 (2) −0.0104 (16) 0.0337 (16) −0.0064 (17)C22 0.095 (3) 0.082 (3) 0.118 (3) −0.030 (2) 0.063 (3) −0.014 (3)C23 0.106 (4) 0.144 (5) 0.185 (6) −0.057 (3) 0.012 (4) −0.065 (4)C24A 0.114 (10) 0.104 (9) 0.121 (11) −0.043 (7) 0.042 (8) −0.054 (7)C25A 0.22 (2) 0.102 (10) 0.23 (2) −0.045 (14) 0.080 (17) −0.060 (10)C24B 0.044 (6) 0.068 (6) 0.094 (8) 0.012 (4) −0.018 (4) 0.002 (5)C25B 0.049 (6) 0.086 (8) 0.064 (6) 0.004 (5) 0.011 (4) 0.003 (5)C26 0.141 (4) 0.122 (4) 0.099 (3) 0.044 (3) 0.018 (3) −0.030 (3)Geometric parameters (Å, º) O1—C01 1.370 (3) C15—H15B 0.9900O1—C11 1.434 (3) C16—H16A 0.9800O2—C03 1.364 (3) C16—H16B 0.9800O2—C21 1.432 (3) C16—H16C 0.9800C01—C06 1.384 (3) C21—C22 1.514 (4)C01—C02 1.390 (3) C21—H21A 0.9900C02—C03 1.385 (3) C21—H21B 0.9900C02—H02A 0.9500 C22—C23 1.450 (6)C03—C04 1.407 (3) C22—H22A 0.9900C04—C05 1.382 (3) C22—H22B 0.9900C04—C07 1.489 (3) C23—C24B 1.547 (8)C05—C06 1.391 (3) C23—C24A 1.603 (8)C05—H05A 0.9500 C23—H23A 0.9900C06—H06A 0.9500 C23—H23B 0.9900C07—N08 1.350 (3) C23—H23C 0.9900C07—C009 1.392 (3) C23—H23D 0.9899N08—C07i 1.350 (3) C24A—C25A 1.23 (2)C009—C010 1.377 (3) C24A—H24A 0.9900C009—H09A 0.9500 C24A—H24B 0.9900C010—C009i 1.377 (3) C25A—C26 1.352 (16)C010—H01C 0.9500 C25A—H25A 0.9900C11—C12 1.509 (3) C25A—H25B 0.9900C11—H11A 0.9900 C24B—C25B 1.563 (18)C11—H11B 0.9900 C24B—H24C 0.9900C12—C13 1.520 (4) C24B—H24D 0.9900supporting informationsup-5Acta Cryst. (2005). E61, o368–o369    C12—H12A 0.9900 C25B—C26 1.654 (16)C12—H12B 0.9900 C25B—H25C 0.9900C13—C14 1.515 (3) C25B—H25D 0.9900C13—H13A 0.9900 C26—H26A 0.9800C13—H13B 0.9900 C26—H26B 0.9800C14—C15 1.508 (3) C26—H26C 0.9800C14—H14A 0.9900 C26—H26D 0.9800C14—H14B 0.9900 C26—H26E 0.9799C15—C16 1.519 (4) C26—H26F 0.9800C15—H15A 0.9900C01—O1—C11 117.5 (2) H16B—C16—H16C 109.5C03—O2—C21 120.7 (2) O2—C21—C22 105.5 (2)O1—C01—C06 124.5 (2) O2—C21—H21A 110.7O1—C01—C02 115.2 (2) C22—C21—H21A 110.7C06—C01—C02 120.2 (2) O2—C21—H21B 110.7C03—C02—C01 120.5 (2) C22—C21—H21B 110.7C03—C02—H02A 119.7 H21A—C21—H21B 108.8C01—C02—H02A 119.7 C23—C22—C21 114.9 (4)O2—C03—C02 123.2 (2) C23—C22—H22A 108.5O2—C03—C04 116.3 (2) C21—C22—H22A 108.5C02—C03—C04 120.5 (2) C23—C22—H22B 108.5C05—C04—C03 117.2 (2) C21—C22—H22B 108.5C05—C04—C07 119.4 (2) H22A—C22—H22B 107.5C03—C04—C07 123.3 (2) C22—C23—C24B 133.3 (6)C04—C05—C06 123.3 (2) C22—C23—C24A 100.1 (7)C04—C05—H05A 118.4 C22—C23—H23A 111.8C06—C05—H05A 118.4 C24B—C23—H23A 102.6C01—C06—C05 118.3 (2) C24A—C23—H23A 111.8C01—C06—H06A 120.9 C22—C23—H23B 111.8C05—C06—H06A 120.9 C24B—C23—H23B 83.9N08—C07—C009 121.7 (2) C24A—C23—H23B 111.7N08—C07—C04 115.1 (2) H23A—C23—H23B 109.5C009—C07—C04 123.1 (2) C22—C23—H23C 105.4C07i—N08—C07 118.6 (3) C24B—C23—H23C 104.0C010—C009—C07 119.5 (3) C24A—C23—H23C 107.3C010—C009—H09A 120.3 H23B—C23—H23C 118.7C07—C009—H09A 120.3 C22—C23—H23D 104.8C009—C010—C009i 119.0 (3) C24B—C23—H23D 100.9C009—C010—H01C 120.5 C24A—C23—H23D 130.7C009i—C010—H01C 120.5 H23C—C23—H23D 106.1O1—C11—C12 107.8 (2) C25A—C24A—C23 123.3 (15)O1—C11—H11A 110.2 C25A—C24A—H24A 106.5C12—C11—H11A 110.2 C23—C24A—H24A 106.5O1—C11—H11B 110.2 C25A—C24A—H24B 106.5C12—C11—H11B 110.2 C23—C24A—H24B 106.5H11A—C11—H11B 108.5 H24A—C24A—H24B 106.5C11—C12—C13 112.3 (2) C24A—C25A—C26 139.6 (19)supporting informationsup-6Acta Cryst. (2005). E61, o368–o369    C11—C12—H12A 109.1 C24A—C25A—H25A 102.2C13—C12—H12A 109.1 C26—C25A—H25A 102.2C11—C12—H12B 109.1 C24A—C25A—H25B 102.1C13—C12—H12B 109.1 C26—C25A—H25B 102.2H12A—C12—H12B 107.9 H25A—C25A—H25B 104.8C14—C13—C12 112.9 (2) C23—C24B—C25B 101.7 (9)C14—C13—H13A 109.0 C23—C24B—H24C 111.4C12—C13—H13A 109.0 C25B—C24B—H24C 111.4C14—C13—H13B 109.0 C23—C24B—H24D 111.4C12—C13—H13B 109.0 C25B—C24B—H24D 111.4H13A—C13—H13B 107.8 C24B—C25B—C26 102.6 (7)C15—C14—C13 113.9 (2) C24B—C25B—H25D 111.3C15—C14—H14A 108.8 C26—C25B—H25D 111.3C13—C14—H14A 108.8 C25A—C26—H26A 109.5C15—C14—H14B 108.8 C25B—C26—H26A 117.5C13—C14—H14B 108.8 C25A—C26—H26B 109.5H14A—C14—H14B 107.7 C25B—C26—H26B 123.8C14—C15—C16 113.9 (2) H26A—C26—H26B 109.5C14—C15—H15A 108.8 C25A—C26—H26C 109.4C16—C15—H15A 108.8 C25B—C26—H26C 82.7C14—C15—H15B 108.8 H26A—C26—H26C 109.5C16—C15—H15B 108.8 H26B—C26—H26C 109.5H15A—C15—H15B 107.7 C25B—C26—H26D 108.2C15—C16—H16A 109.5 C25B—C26—H26E 108.6C15—C16—H16B 109.5 H26D—C26—H26E 109.5H16A—C16—H16B 109.5 C25B—C26—H26F 111.6C15—C16—H16C 109.5 H26D—C26—H26F 109.5H16A—C16—H16C 109.5 H26E—C26—H26F 109.5Symmetry code: (i) −x+1/2, y, −z+1/2.

2,6-Bis[2,4-bis(heptyloxy)phenyl]pyridine

https://orca.cardiff.ac.uk/id/eprint/155143/1/tk6205.pdf

2,6-Bis[2,4-bis(heptyloxy)phenyl]pyridine

Abstract

Similar works

Full text

Available Versions

Online Research @ Cardiff