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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2570.
Published online 2009 September 30. doi:  10.1107/S1600536809038707
PMCID: PMC2970165

1,4-Bis(4-pyridylmeth­oxy)benzene

Abstract

The mol­ecule of the title compound, C18H16N2O2, lies about a center of inversion. The central phenyl­ene ring is aligned at 62.7 (1)° with respect to the pyridyl ring. In the crystal, weak inter­molecular C—H(...)N hydrogen bonds link mol­ecules into sheets parallel to (104). C—H(...)O inter­actions are also present.

Related literature

For general background to metal-organic complexes with flexible pyridyl-based ligands, see: Hou et al. (2001 [triangle]). For details of the synthesis, see Gao et al. (2004 [triangle]). For related structures, see: Gao et al. (2006 [triangle], 2009a [triangle],b [triangle]).

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Object name is e-65-o2570-scheme1.jpg

Experimental

Crystal data

  • C18H16N2O2
  • M r = 292.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2570-efi1.jpg
  • a = 6.7825 (14) Å
  • b = 5.8694 (12) Å
  • c = 18.542 (4) Å
  • β = 90.99 (3)°
  • V = 738.0 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 291 K
  • 0.22 × 0.17 × 0.15 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.981, T max = 0.987
  • 6972 measured reflections
  • 1692 independent reflections
  • 1381 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.123
  • S = 1.09
  • 1692 reflections
  • 100 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 [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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038707/ng2651sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038707/ng2651Isup2.hkl

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

Acknowledgments

The authors thank the Specialized Research Funds for Technological Innovative Talent in Harbin (RC2009XK018007) and Heilongjiang University for orting this study.

supplementary crystallographic information

Comment

The metal-organic complexes with flexible pyridyl-based ligands have been rapidly developed in the past few years owing to their abundant topology structures and potential applications. Hou's group (2001) has reported the synthesis of 1,4-bis(4-pyridylmethoxy)benzene ligand, which reacted with Cd(NO3)2.6H2O and Co(NCS)2 to assemble into one-dimensional chain and two-dimensional plane network structures, respectively. It is worthy to note that the former cadmium complex consists of two kinds of chains: double zigzag linear chain and ladder-like one-dimensional chain. Our group has report three kinds of flexible pyridyl-based ligands in the previous report (Gao et al. 2006; Gao et al. 2009a; Gao et al. 2009b). As an extension of our work about bipyridyl aromatic ligands, we have synthesized and report the crystal structure of the title compound here.

In the title compound, the 1,4-bis(4-pyridylmethoxy)benzene ligand is centrosymmetric. The planes of two terminal pyridyl groups distort drastically and have dihedral angles of 62.7 (1)62.7 (1)° with the plane of the central benzene ring (Figure 1).

Within the packing structure,the adjacent 1,4-bis(4-pyridylmethoxy)benzene molecules are linked into two-dimensional wavy structure in (104) direction by intermolecular C—H···N hydrogen bonds interactions existing in the terminal pyridine rings (Figure 2, Table 1).

Experimental

The 1,4-bis(4-pyridylmethoxy)benzene was synthesized by the reaction of p-benzenediol and 4-chloromethylpyridine hydrochloride under nitrogen atmosphere and alkaline condition (Gao et al., 2004; Gao et al., 2006). Colourless block-shaped crystals of title compound were obtained by slow evaporation of an methanol solution after several days.

Refinement

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

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level for non-H atoms. [Symmetry codes: (i) -x, -y, 1 - z]
Fig. 2.
A partial packing view, showing the two-dimensional hydrogen bonding sheet. Dashed lines indicate the hydrogen-bonding interactions.

Crystal data

C18H16N2O2F(000) = 308
Mr = 292.33Dx = 1.315 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5914 reflections
a = 6.7825 (14) Åθ = 3.0–27.5°
b = 5.8694 (12) ŵ = 0.09 mm1
c = 18.542 (4) ÅT = 291 K
β = 90.99 (3)°Block, colorless
V = 738.0 (3) Å30.22 × 0.17 × 0.15 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer1692 independent reflections
Radiation source: fine-focus sealed tube1381 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −8→8
Tmin = 0.981, Tmax = 0.987k = −7→7
6972 measured reflectionsl = −24→23

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0725P)2 + 0.0696P] where P = (Fo2 + 2Fc2)/3
1692 reflections(Δ/σ)max < 0.001
100 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.22 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
C10.7686 (2)0.6857 (2)0.33856 (8)0.0480 (4)
H10.83100.82360.34850.058*
C20.5902 (2)0.6432 (2)0.37093 (7)0.0432 (3)
H20.53550.75000.40180.052*
C30.49406 (16)0.43997 (19)0.35690 (6)0.0328 (3)
C40.58453 (18)0.2877 (2)0.31094 (6)0.0382 (3)
H40.52530.14870.30020.046*
C50.76321 (19)0.3441 (2)0.28130 (7)0.0438 (3)
H50.82210.23940.25080.053*
C60.29658 (18)0.3853 (2)0.38841 (7)0.0416 (3)
H6A0.24710.51550.41480.050*
H6B0.20230.34750.35030.050*
C70.15772 (16)0.1050 (2)0.46653 (6)0.0336 (3)
C8−0.03138 (17)0.1943 (2)0.45833 (6)0.0367 (3)
H8−0.05280.32450.43070.044*
C9−0.18785 (16)0.0872 (2)0.49178 (7)0.0372 (3)
H9−0.31460.14570.48600.045*
N10.85625 (16)0.5413 (2)0.29416 (6)0.0466 (3)
O10.32347 (12)0.19635 (16)0.43566 (5)0.0472 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0399 (7)0.0388 (7)0.0657 (9)−0.0104 (5)0.0077 (6)0.0038 (6)
C20.0412 (7)0.0387 (6)0.0501 (7)−0.0021 (5)0.0115 (5)−0.0033 (5)
C30.0271 (6)0.0359 (6)0.0357 (6)−0.0002 (4)0.0062 (4)0.0068 (5)
C40.0342 (6)0.0350 (6)0.0455 (7)−0.0027 (5)0.0060 (5)0.0000 (5)
C50.0362 (7)0.0479 (7)0.0476 (7)0.0044 (5)0.0127 (5)−0.0008 (6)
C60.0304 (6)0.0433 (7)0.0515 (7)0.0007 (5)0.0128 (5)0.0121 (6)
C70.0233 (5)0.0431 (6)0.0344 (6)−0.0040 (4)0.0052 (4)0.0048 (5)
C80.0282 (6)0.0422 (6)0.0400 (6)0.0007 (5)0.0048 (5)0.0111 (5)
C90.0214 (5)0.0483 (7)0.0421 (6)0.0020 (4)0.0045 (4)0.0091 (5)
N10.0320 (6)0.0504 (7)0.0578 (7)−0.0028 (4)0.0127 (5)0.0106 (5)
O10.0229 (4)0.0619 (6)0.0572 (6)−0.0021 (4)0.0080 (4)0.0273 (5)

Geometric parameters (Å, °)

C1—N11.3293 (18)C6—O11.4231 (15)
C1—C21.3829 (19)C6—H6A0.9700
C1—H10.9300C6—H6B0.9700
C2—C31.3818 (17)C7—O11.3789 (13)
C2—H20.9300C7—C9i1.3806 (17)
C3—C41.3854 (16)C7—C81.3914 (16)
C3—C61.5051 (15)C8—C91.3888 (16)
C4—C51.3795 (17)C8—H80.9300
C4—H40.9300C9—C7i1.3806 (17)
C5—N11.3379 (18)C9—H90.9300
C5—H50.9300
N1—C1—C2123.89 (12)O1—C6—H6A110.2
N1—C1—H1118.1C3—C6—H6A110.2
C2—C1—H1118.1O1—C6—H6B110.2
C3—C2—C1119.20 (12)C3—C6—H6B110.2
C3—C2—H2120.4H6A—C6—H6B108.5
C1—C2—H2120.4O1—C7—C9i115.87 (10)
C2—C3—C4117.39 (11)O1—C7—C8124.38 (11)
C2—C3—C6122.08 (11)C9i—C7—C8119.75 (10)
C4—C3—C6120.52 (11)C9—C8—C7119.39 (11)
C5—C4—C3119.47 (11)C9—C8—H8120.3
C5—C4—H4120.3C7—C8—H8120.3
C3—C4—H4120.3C7i—C9—C8120.86 (11)
N1—C5—C4123.45 (12)C7i—C9—H9119.6
N1—C5—H5118.3C8—C9—H9119.6
C4—C5—H5118.3C1—N1—C5116.60 (11)
O1—C6—C3107.44 (10)C7—O1—C6117.51 (9)

Symmetry codes: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···N1ii0.932.623.4499 (18)149
C9—H9···O1iii0.932.633.5156 (17)160

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2651).

References

  • Gao, C.-M., Cao, D. & Zhu, L. (2004). Photogr. Sci. Photochem.22, 103–107.
  • Gao, J.-S., Liu, Y., Hou, G.-F., Yu, Y.-H. & Yan, P.-F. (2006). Acta Cryst. E62, o5645–o5646.
  • Gao, J.-S., Liu, Y., Zhang, S., Hou, G.-F. & Yan, P.-F. (2009a). Acta Cryst. E65, o2432. [PMC free article] [PubMed]
  • Gao, J.-S., Liu, Y., Zhang, S., Zuo, D.-F. & Hou, G.-F. (2009b). Acta Cryst. E65, o2457. [PMC free article] [PubMed]
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Hou, H.-W., Fan, Y.-T., Zhang, L.-P., Du, C.-X. & Zhu, Y. (2001). Inorg. Chem. Commun.4, 168–172.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalClear Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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