1,4-Bis(4-pyridylmeth­oxy)benzene

Zou, P.; Liu, Y.; Zhang, S.; Wang, X.; Gao, J.-S.

doi:10.1107/S1600536809038707

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2570

doi:10.1107/S1600536809038707

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1,4-Bis(4-pyridylmethoxy)benzene

Ping Zou,^a Ying Liu,^b Shuang Zhang,^b Xue Wang ^b and Jin-Sheng Gao ^b ^*

^aCollege of Life Science, Sichuan Agriculture University, Yaan 625014, People's Republic of China, and ^bCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 23 September 2009; accepted 24 September 2009; online 30 September 2009)

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 ). For details of the synthesis, see Gao et al. (2004 ). For related structures, see: Gao et al. (2006 , 2009a ,b ).

Experimental

Crystal data

C₁₈H₁₆N₂O₂
M_r = 292.33
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.123
S = 1.09
1692 reflections
100 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N1ⁱ	0.93	2.62	3.4499 (18)	149
C9—H9⋯O1ⁱⁱ	0.93	2.63	3.5156 (17)	160
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	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.

1,4-Bis(4-pyridylmethoxy)benzene top

Crystal data top

C₁₈H₁₆N₂O₂	F(000) = 308
M_r = 292.33	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5914 reflections
a = 6.7825 (14) Å	θ = 3.0–27.5°
b = 5.8694 (12) Å	µ = 0.09 mm⁻¹
c = 18.542 (4) Å	T = 291 K
β = 90.99 (3)°	Block, colorless
V = 738.0 (3) Å³	0.22 × 0.17 × 0.15 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	1692 independent reflections
Radiation source: fine-focus sealed tube	1381 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
T_min = 0.981, T_max = 0.987	k = −7→7
6972 measured reflections	l = −24→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0725P)² + 0.0696P] where P = (F_o² + 2F_c²)/3
1692 reflections	(Δ/σ)_max < 0.001
100 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₂	V = 738.0 (3) Å³
M_r = 292.33	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.7825 (14) Å	µ = 0.09 mm⁻¹
b = 5.8694 (12) Å	T = 291 K
c = 18.542 (4) Å	0.22 × 0.17 × 0.15 mm
β = 90.99 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	1692 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1381 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.987	R_int = 0.025
6972 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.09	Δρ_max = 0.25 e Å⁻³
1692 reflections	Δρ_min = −0.22 e Å⁻³
100 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

	x	y	z	U_iso*/U_eq
C1	0.7686 (2)	0.6857 (2)	0.33856 (8)	0.0480 (4)
H1	0.8310	0.8236	0.3485	0.058*
C2	0.5902 (2)	0.6432 (2)	0.37093 (7)	0.0432 (3)
H2	0.5355	0.7500	0.4018	0.052*
C3	0.49406 (16)	0.43997 (19)	0.35690 (6)	0.0328 (3)
C4	0.58453 (18)	0.2877 (2)	0.31094 (6)	0.0382 (3)
H4	0.5253	0.1487	0.3002	0.046*
C5	0.76321 (19)	0.3441 (2)	0.28130 (7)	0.0438 (3)
H5	0.8221	0.2394	0.2508	0.053*
C6	0.29658 (18)	0.3853 (2)	0.38841 (7)	0.0416 (3)
H6A	0.2471	0.5155	0.4148	0.050*
H6B	0.2023	0.3475	0.3503	0.050*
C7	0.15772 (16)	0.1050 (2)	0.46653 (6)	0.0336 (3)
C8	−0.03138 (17)	0.1943 (2)	0.45833 (6)	0.0367 (3)
H8	−0.0528	0.3245	0.4307	0.044*
C9	−0.18785 (16)	0.0872 (2)	0.49178 (7)	0.0372 (3)
H9	−0.3146	0.1457	0.4860	0.045*
N1	0.85625 (16)	0.5413 (2)	0.29416 (6)	0.0466 (3)
O1	0.32347 (12)	0.19635 (16)	0.43566 (5)	0.0472 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0399 (7)	0.0388 (7)	0.0657 (9)	−0.0104 (5)	0.0077 (6)	0.0038 (6)
C2	0.0412 (7)	0.0387 (6)	0.0501 (7)	−0.0021 (5)	0.0115 (5)	−0.0033 (5)
C3	0.0271 (6)	0.0359 (6)	0.0357 (6)	−0.0002 (4)	0.0062 (4)	0.0068 (5)
C4	0.0342 (6)	0.0350 (6)	0.0455 (7)	−0.0027 (5)	0.0060 (5)	0.0000 (5)
C5	0.0362 (7)	0.0479 (7)	0.0476 (7)	0.0044 (5)	0.0127 (5)	−0.0008 (6)
C6	0.0304 (6)	0.0433 (7)	0.0515 (7)	0.0007 (5)	0.0128 (5)	0.0121 (6)
C7	0.0233 (5)	0.0431 (6)	0.0344 (6)	−0.0040 (4)	0.0052 (4)	0.0048 (5)
C8	0.0282 (6)	0.0422 (6)	0.0400 (6)	0.0007 (5)	0.0048 (5)	0.0111 (5)
C9	0.0214 (5)	0.0483 (7)	0.0421 (6)	0.0020 (4)	0.0045 (4)	0.0091 (5)
N1	0.0320 (6)	0.0504 (7)	0.0578 (7)	−0.0028 (4)	0.0127 (5)	0.0106 (5)
O1	0.0229 (4)	0.0619 (6)	0.0572 (6)	−0.0021 (4)	0.0080 (4)	0.0273 (5)

Geometric parameters (Å, º) top

C1—N1	1.3293 (18)	C6—O1	1.4231 (15)
C1—C2	1.3829 (19)	C6—H6A	0.9700
C1—H1	0.9300	C6—H6B	0.9700
C2—C3	1.3818 (17)	C7—O1	1.3789 (13)
C2—H2	0.9300	C7—C9ⁱ	1.3806 (17)
C3—C4	1.3854 (16)	C7—C8	1.3914 (16)
C3—C6	1.5051 (15)	C8—C9	1.3888 (16)
C4—C5	1.3795 (17)	C8—H8	0.9300
C4—H4	0.9300	C9—C7ⁱ	1.3806 (17)
C5—N1	1.3379 (18)	C9—H9	0.9300
C5—H5	0.9300

N1—C1—C2	123.89 (12)	O1—C6—H6A	110.2
N1—C1—H1	118.1	C3—C6—H6A	110.2
C2—C1—H1	118.1	O1—C6—H6B	110.2
C3—C2—C1	119.20 (12)	C3—C6—H6B	110.2
C3—C2—H2	120.4	H6A—C6—H6B	108.5
C1—C2—H2	120.4	O1—C7—C9ⁱ	115.87 (10)
C2—C3—C4	117.39 (11)	O1—C7—C8	124.38 (11)
C2—C3—C6	122.08 (11)	C9ⁱ—C7—C8	119.75 (10)
C4—C3—C6	120.52 (11)	C9—C8—C7	119.39 (11)
C5—C4—C3	119.47 (11)	C9—C8—H8	120.3
C5—C4—H4	120.3	C7—C8—H8	120.3
C3—C4—H4	120.3	C7ⁱ—C9—C8	120.86 (11)
N1—C5—C4	123.45 (12)	C7ⁱ—C9—H9	119.6
N1—C5—H5	118.3	C8—C9—H9	119.6
C4—C5—H5	118.3	C1—N1—C5	116.60 (11)
O1—C6—C3	107.44 (10)	C7—O1—C6	117.51 (9)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1ⁱⁱ	0.93	2.62	3.4499 (18)	149
C9—H9···O1ⁱⁱⁱ	0.93	2.63	3.5156 (17)	160

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₂
M_r	292.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	6.7825 (14), 5.8694 (12), 18.542 (4)
β (°)	90.99 (3)
V (Å³)	738.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.17 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.981, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	6972, 1692, 1381
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.123, 1.09
No. of reflections	1692
No. of parameters	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1ⁱ	0.93	2.62	3.4499 (18)	148.8
C9—H9···O1ⁱⁱ	0.93	2.63	3.5156 (17)	159.8

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

Acknowledgements

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

References

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