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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2756.
Published online 2010 October 9. doi:  10.1107/S1600536810039413
PMCID: PMC3009191

4′-[4-(Pyridin-2-yl)phen­yl]-2,2′:6′,2′′-terpyridine

Abstract

In the title compound, C26H18N4, each ring is almost planar with maximum deviation of 0.012 (5) Å. In the crystal, mol­ecules are stacked by weak C—H(...)π inter­actions, forming a three-dimensional framework.

Related literature

For the uses and the synthesis of the title compound, see: Arm et al. (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-66-o2756-scheme1.jpg

Experimental

Crystal data

  • C26H18N4
  • M r = 386.44
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2756-efi1.jpg
  • a = 11.056 (2) Å
  • b = 16.113 (3) Å
  • c = 11.748 (2) Å
  • β = 109.05 (3)°
  • V = 1978.2 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.30 × 0.20 × 0.05 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.977, T max = 0.996
  • 3778 measured reflections
  • 3585 independent reflections
  • 1576 reflections with I > 2σ(I)
  • R int = 0.100
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.217
  • S = 0.88
  • 3585 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); 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 I, Is1. DOI: 10.1107/S1600536810039413/bq2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039413/bq2233Isup2.hkl

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

supplementary crystallographic information

Comment

4'-(4-(Pyridin-2-yl)phenyl)-2,2':6',2''-terpyridine, (I), is an important intermediate used to synthesize luminescent transition metal complexes, which are potentially interesting components of new molecular sensors for detection of molecules or ions in aqueous solution (Arm et al., 2006). We report here the crystal structure of the title compound (Fig. 1).

Bond lengths (Allen et al., 1987) and angles of (I) are within normal ranges. In (I), each ring is planar with the max. deviation 0.012 (5) Å. The dihedral angles of the rings A (C1—C5/N1), B(C6—C11), C(C12—C16/N2), D(C17—C21/N3), E(C22—C26/N4) are: A/B = 159.6 (2)°, C/B = 158.5 (2)°, D/A = 4.8 (1)°, E/A = 170.6 (3)°.

In the crystal structure, no obvious hydrogen bond was observed, and molecules were stacked to form a three-dimensional framework by two C—H···π weak interactions, which may be effective for the stabilization of the crystal (Table 1, Fig 2).

Experimental

The title compound (I) was prepared by the method reported in literature (Arm et al., 2006). Single crystals were obtained by dissolving the title compound (0.5 g, 1.3 mmol) in ethanol (100 ml) and evaporating the solvent slowly at room temperature for about 20 d.

Refinement

After checking their presence in the difference map, all the H atoms were positioned geometrically [C—H = 0.93 Å] and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Crystal packing of the title compound.

Crystal data

C26H18N4F(000) = 808
Mr = 386.44Dx = 1.298 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.056 (2) Åθ = 9–12°
b = 16.113 (3) ŵ = 0.08 mm1
c = 11.748 (2) ÅT = 298 K
β = 109.05 (3)°Block, colorless
V = 1978.2 (7) Å30.30 × 0.20 × 0.05 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer1576 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.100
graphiteθmax = 25.3°, θmin = 2.0°
ω/2θ scansh = 0→13
Absorption correction: ψ scan (North et al., 1968)k = 0→19
Tmin = 0.977, Tmax = 0.996l = −14→13
3778 measured reflections3 standard reflections every 200 reflections
3585 independent reflections intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217H-atom parameters constrained
S = 0.88w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3585 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.16 e Å3

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 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)

xyzUiso*/Ueq
N10.0183 (4)0.5691 (3)−0.2077 (3)0.0771 (12)
C10.1554 (4)0.6611 (3)−0.2631 (4)0.0634 (12)
H1B0.22550.6967−0.24010.076*
N20.5599 (3)0.65373 (19)0.5784 (3)0.0471 (8)
C20.0865 (5)0.6503 (3)−0.3842 (4)0.0801 (15)
H2B0.11140.6769−0.44330.096*
N30.7514 (3)0.7844 (2)0.4578 (3)0.0615 (10)
C3−0.0173 (5)0.6003 (4)−0.4147 (4)0.0881 (16)
H3B−0.06710.5933−0.49490.106*
N40.3280 (3)0.5058 (2)0.6038 (3)0.0554 (9)
C4−0.0471 (5)0.5607 (4)−0.3254 (4)0.102 (2)
H4B−0.11750.5254−0.34720.122*
C50.1198 (4)0.6189 (3)−0.1773 (3)0.0527 (11)
C60.1957 (4)0.6248 (2)−0.0466 (3)0.0482 (10)
C70.2778 (4)0.6900 (3)−0.0008 (3)0.0631 (12)
H7A0.28540.7321−0.05210.076*
C80.3490 (4)0.6939 (3)0.1201 (3)0.0627 (12)
H8A0.40350.73880.14790.075*
C90.3417 (4)0.6330 (2)0.2014 (3)0.0458 (10)
C100.2592 (4)0.5674 (2)0.1543 (3)0.0516 (10)
H10A0.25240.52470.20510.062*
C110.1874 (4)0.5641 (2)0.0346 (3)0.0540 (11)
H11A0.13160.51980.00690.065*
C120.4183 (4)0.6392 (2)0.3317 (3)0.0451 (10)
C130.5279 (4)0.6881 (2)0.3720 (3)0.0504 (10)
H13A0.55610.71650.31650.060*
C140.5960 (4)0.6950 (2)0.4949 (3)0.0464 (10)
C150.4563 (4)0.6052 (2)0.5413 (3)0.0433 (9)
C160.3837 (4)0.5966 (2)0.4191 (3)0.0483 (10)
H16A0.31210.56230.39670.058*
C170.7120 (4)0.7465 (2)0.5409 (3)0.0459 (9)
C180.8562 (4)0.8311 (3)0.4969 (4)0.0724 (14)
H18A0.88510.85720.43990.087*
C190.9243 (4)0.8431 (3)0.6170 (4)0.0694 (13)
H19A0.99670.87670.64030.083*
C200.8825 (4)0.8045 (3)0.7007 (4)0.0650 (12)
H20A0.92640.81130.78240.078*
C210.7747 (4)0.7551 (3)0.6631 (3)0.0571 (11)
H21A0.74480.72830.71880.069*
C220.4209 (4)0.5621 (2)0.6383 (3)0.0459 (10)
C230.4842 (4)0.5816 (3)0.7587 (3)0.0534 (11)
H23A0.54900.62120.77960.064*
C240.4488 (4)0.5412 (3)0.8459 (3)0.0636 (12)
H24A0.48790.55430.92670.076*
C250.3555 (4)0.4814 (3)0.8129 (3)0.0638 (12)
H25A0.33150.45220.87040.077*
C260.2982 (4)0.4660 (3)0.6910 (4)0.0626 (12)
H26A0.23510.42540.66850.075*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.071 (3)0.105 (3)0.053 (2)−0.025 (2)0.017 (2)−0.008 (2)
C10.070 (3)0.073 (3)0.044 (2)−0.002 (3)0.014 (2)0.000 (2)
N20.056 (2)0.050 (2)0.0383 (17)−0.0039 (17)0.0195 (16)−0.0027 (15)
C20.094 (4)0.102 (4)0.044 (3)0.004 (3)0.021 (3)0.009 (3)
N30.065 (2)0.075 (3)0.048 (2)−0.011 (2)0.0235 (19)0.0061 (18)
C30.093 (4)0.115 (5)0.047 (3)−0.009 (4)0.010 (3)−0.008 (3)
N40.066 (2)0.065 (2)0.0406 (19)−0.010 (2)0.0247 (17)0.0004 (17)
C40.091 (4)0.144 (6)0.062 (3)−0.045 (4)0.013 (3)−0.020 (3)
C50.055 (3)0.065 (3)0.040 (2)0.003 (2)0.018 (2)−0.003 (2)
C60.053 (2)0.054 (3)0.041 (2)0.002 (2)0.0200 (19)0.0002 (19)
C70.082 (3)0.068 (3)0.037 (2)−0.020 (3)0.016 (2)0.006 (2)
C80.088 (3)0.057 (3)0.042 (2)−0.024 (3)0.020 (2)0.000 (2)
C90.050 (2)0.051 (2)0.039 (2)0.003 (2)0.0194 (19)−0.0030 (19)
C100.061 (3)0.055 (3)0.039 (2)−0.010 (2)0.017 (2)0.0022 (19)
C110.059 (3)0.058 (3)0.050 (2)−0.011 (2)0.025 (2)−0.003 (2)
C120.057 (3)0.049 (2)0.034 (2)0.006 (2)0.0220 (19)0.0035 (18)
C130.057 (3)0.051 (2)0.047 (2)0.001 (2)0.023 (2)0.0008 (19)
C140.058 (2)0.046 (2)0.041 (2)0.002 (2)0.0233 (19)0.0005 (18)
C150.051 (2)0.044 (2)0.039 (2)0.003 (2)0.0202 (19)−0.0022 (17)
C160.058 (3)0.053 (2)0.037 (2)−0.005 (2)0.0208 (19)−0.0054 (18)
C170.056 (2)0.047 (2)0.037 (2)0.001 (2)0.0191 (18)−0.0026 (18)
C180.078 (3)0.084 (4)0.059 (3)−0.021 (3)0.027 (3)0.003 (3)
C190.069 (3)0.072 (3)0.071 (3)−0.014 (3)0.027 (3)−0.002 (3)
C200.067 (3)0.074 (3)0.049 (3)−0.008 (3)0.014 (2)−0.013 (2)
C210.063 (3)0.070 (3)0.040 (2)−0.007 (2)0.020 (2)−0.003 (2)
C220.058 (3)0.041 (2)0.044 (2)0.006 (2)0.023 (2)0.0038 (18)
C230.062 (3)0.057 (3)0.041 (2)−0.002 (2)0.017 (2)0.0040 (19)
C240.079 (3)0.075 (3)0.033 (2)−0.001 (3)0.014 (2)0.013 (2)
C250.076 (3)0.076 (3)0.044 (3)−0.002 (3)0.025 (2)0.017 (2)
C260.067 (3)0.072 (3)0.050 (3)−0.015 (2)0.021 (2)0.008 (2)

Geometric parameters (Å, °)

N1—C51.330 (5)C10—H10A0.9300
N1—C41.342 (5)C11—H11A0.9300
C1—C51.376 (5)C12—C161.389 (5)
C1—C21.388 (5)C12—C131.392 (5)
C1—H1B0.9300C13—C141.398 (5)
N2—C151.338 (4)C13—H13A0.9300
N2—C141.348 (4)C14—C171.474 (5)
C2—C31.351 (7)C15—C161.404 (5)
C2—H2B0.9300C15—C221.491 (5)
N3—C181.332 (5)C16—H16A0.9300
N3—C171.339 (4)C17—C211.382 (5)
C3—C41.358 (7)C18—C191.379 (5)
C3—H3B0.9300C18—H18A0.9300
N4—C221.331 (5)C19—C201.366 (5)
N4—C261.339 (4)C19—H19A0.9300
C4—H4B0.9300C20—C211.380 (5)
C5—C61.493 (5)C20—H20A0.9300
C6—C71.378 (5)C21—H21A0.9300
C6—C111.390 (5)C22—C231.394 (5)
C7—C81.382 (5)C23—C241.374 (5)
C7—H7A0.9300C23—H23A0.9300
C8—C91.390 (5)C24—C251.372 (6)
C8—H8A0.9300C24—H24A0.9300
C9—C101.387 (5)C25—C261.386 (5)
C9—C121.492 (5)C25—H25A0.9300
C10—C111.372 (5)C26—H26A0.9300
C5—N1—C4117.5 (4)C12—C13—H13A119.6
C5—C1—C2119.8 (4)C14—C13—H13A119.6
C5—C1—H1B120.1N2—C14—C13121.6 (4)
C2—C1—H1B120.1N2—C14—C17116.1 (3)
C15—N2—C14118.5 (3)C13—C14—C17122.3 (3)
C3—C2—C1118.8 (5)N2—C15—C16122.3 (3)
C3—C2—H2B120.6N2—C15—C22115.7 (3)
C1—C2—H2B120.6C16—C15—C22122.0 (4)
C18—N3—C17117.4 (4)C12—C16—C15120.2 (4)
C2—C3—C4118.4 (5)C12—C16—H16A119.9
C2—C3—H3B120.8C15—C16—H16A119.9
C4—C3—H3B120.8N3—C17—C21122.6 (4)
C22—N4—C26116.9 (3)N3—C17—C14116.2 (3)
N1—C4—C3124.3 (5)C21—C17—C14121.3 (3)
N1—C4—H4B117.9N3—C18—C19123.7 (4)
C3—C4—H4B117.9N3—C18—H18A118.2
N1—C5—C1121.3 (4)C19—C18—H18A118.2
N1—C5—C6117.1 (4)C20—C19—C18118.2 (4)
C1—C5—C6121.5 (4)C20—C19—H19A120.9
C7—C6—C11116.8 (4)C18—C19—H19A120.9
C7—C6—C5121.9 (4)C19—C20—C21119.5 (4)
C11—C6—C5121.4 (4)C19—C20—H20A120.3
C6—C7—C8121.2 (4)C21—C20—H20A120.3
C6—C7—H7A119.4C20—C21—C17118.6 (4)
C8—C7—H7A119.4C20—C21—H21A120.7
C7—C8—C9122.2 (4)C17—C21—H21A120.7
C7—C8—H8A118.9N4—C22—C23123.0 (3)
C9—C8—H8A118.9N4—C22—C15116.9 (3)
C10—C9—C8116.2 (3)C23—C22—C15120.1 (4)
C10—C9—C12122.6 (3)C24—C23—C22118.6 (4)
C8—C9—C12121.2 (4)C24—C23—H23A120.7
C11—C10—C9121.6 (4)C22—C23—H23A120.7
C11—C10—H10A119.2C25—C24—C23119.6 (4)
C9—C10—H10A119.2C25—C24—H24A120.2
C10—C11—C6122.0 (4)C23—C24—H24A120.2
C10—C11—H11A119.0C24—C25—C26117.7 (4)
C6—C11—H11A119.0C24—C25—H25A121.1
C16—C12—C13116.6 (3)C26—C25—H25A121.1
C16—C12—C9121.7 (4)N4—C26—C25124.2 (4)
C13—C12—C9121.7 (3)N4—C26—H26A117.9
C12—C13—C14120.8 (3)C25—C26—H26A117.9
C5—C1—C2—C32.2 (7)C12—C13—C14—C17−179.8 (3)
C1—C2—C3—C4−2.1 (8)C14—N2—C15—C16−0.6 (5)
C5—N1—C4—C3−0.8 (8)C14—N2—C15—C22−179.3 (3)
C2—C3—C4—N11.5 (10)C13—C12—C16—C151.2 (5)
C4—N1—C5—C10.8 (7)C9—C12—C16—C15−178.6 (3)
C4—N1—C5—C6−177.2 (4)N2—C15—C16—C120.0 (6)
C2—C1—C5—N1−1.6 (7)C22—C15—C16—C12178.6 (3)
C2—C1—C5—C6176.3 (4)C18—N3—C17—C210.8 (6)
N1—C5—C6—C7−161.0 (4)C18—N3—C17—C14−179.9 (4)
C1—C5—C6—C721.0 (6)N2—C14—C17—N3176.9 (3)
N1—C5—C6—C1119.6 (6)C13—C14—C17—N3−2.1 (5)
C1—C5—C6—C11−158.4 (4)N2—C14—C17—C21−3.7 (5)
C11—C6—C7—C80.5 (6)C13—C14—C17—C21177.2 (4)
C5—C6—C7—C8−178.9 (4)C17—N3—C18—C19−0.8 (7)
C6—C7—C8—C9−0.1 (7)N3—C18—C19—C200.5 (7)
C7—C8—C9—C100.4 (6)C18—C19—C20—C210.0 (7)
C7—C8—C9—C12−179.2 (4)C19—C20—C21—C170.0 (6)
C8—C9—C10—C11−1.1 (6)N3—C17—C21—C20−0.4 (6)
C12—C9—C10—C11178.4 (4)C14—C17—C21—C20−179.6 (4)
C9—C10—C11—C61.7 (6)C26—N4—C22—C23−1.4 (6)
C7—C6—C11—C10−1.3 (6)C26—N4—C22—C15178.7 (3)
C5—C6—C11—C10178.1 (4)N2—C15—C22—N4−172.0 (3)
C10—C9—C12—C16−21.2 (6)C16—C15—C22—N49.3 (5)
C8—C9—C12—C16158.4 (4)N2—C15—C22—C238.0 (5)
C10—C9—C12—C13159.0 (4)C16—C15—C22—C23−170.6 (3)
C8—C9—C12—C13−21.4 (6)N4—C22—C23—C24−0.3 (6)
C16—C12—C13—C14−1.8 (5)C15—C22—C23—C24179.6 (4)
C9—C12—C13—C14178.0 (3)C22—C23—C24—C251.9 (6)
C15—N2—C14—C130.0 (5)C23—C24—C25—C26−1.6 (6)
C15—N2—C14—C17−179.0 (3)C22—N4—C26—C251.7 (6)
C12—C13—C14—N21.3 (6)C24—C25—C26—N4−0.2 (7)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N2/C12–C16 and N3/C17–C21 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C7—H7A···Cg1i0.932.973.675 (5)134
C25—H25A···Cg2ii0.933.193.989 (5)146

Symmetry codes: (i) x, −y+1/2, z−3/2; (ii) −x+1, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2233).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Arm, K. J., Leslie, W. & Williams, J. A. G. (2006). Inorg. Chim. Acta, 359, 1222–1232.
  • Enraf–Nonius (1985). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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