1,4-Bis(pyridin-3-ylmeth­oxy)benzene

Gao, J.-S.; Liu, Y.; Zhang, S.; Zuo, D.-F.; Hou, G.-F.

doi:10.1107/S1600536809036265

organic compounds

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Volume 65| Part 10| October 2009| Page o2457

doi:10.1107/S1600536809036265

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1,4-Bis(pyridin-3-ylmethoxy)benzene

Jin-Sheng Gao,^a ^* Ying Liu,^a Shuang Zhang,^a Dian-Fa Zuo ^a and Guang-Feng Hou ^a

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

(Received 4 September 2009; accepted 8 September 2009; online 12 September 2009)

The asymmetric unit of the centrosymmetric title compound, C₁₈H₁₆N₂O₂, contains one half-molecule. The central benzene ring forms a dihedral angle of 66.8 (1)° with two outer aromatic rings. In the crystal structure, weak intermolecular C—H⋯N hydrogen bonds link molecules into sheets parallel to (104).

Related literature

For general background to bridging molecules with pyridyl substituents at the terminal positions, see: McMorran & Steel (1998 ); Zaman et al. (2005 ). For details of the synthesis, see: Gao et al. (2004 ). For a related structure, see: Gao et al. (2006 ).

Experimental

Crystal data

C₁₈H₁₆N₂O₂
M_r = 292.33
Monoclinic, P 2₁ /c
a = 6.852 (5) Å
b = 5.688 (3) Å
c = 18.861 (12) Å
β = 90.60 (3)°
V = 735.0 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 K
0.22 × 0.20 × 0.19 mm

Data collection

Rigaku RAXIS-RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.981, T_max = 0.984
6855 measured reflections
1684 independent reflections
1213 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.118
S = 1.09
1684 reflections
100 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N1ⁱ	0.93	2.57	3.437 (3)	155
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 datablock I. DOI: 10.1107/S1600536809036265/cv2613sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036265/cv2613Isup2.hkl

checkCIF report

Comment top

The bridging molecules with pyridyl substituents at the terminal positions are hoped to construct interesting supramolecular architectures by intermolecular hydrogen bonding and coordination with metals. McMorran' group have reported the synthesis of a quadruply stranded helicate that encapsulates a hexafluorophosphate anion by the reaction of 1,4-bis(3-pyridylmethoxy)benzene with palladium chlorate (McMorran et al., 1998). Zaman's group have designed a long rigid organic ligand, 1,4-bis[(3-pyridyl)ethynyl]benzene, which reacted with metal salts to form interpenetrating two-dimensional and three-dimensional cross-zigzag chains and metallocyclic chain structures (Zaman et al., 2005). As an extension of our work about bipyridyl aromatic ligands, we report the crystal structure of the title compound here.

In the title compound (Fig. 1), all bond lengths and angles are normal and correpond to those observed in the related compound (Gao et al., 2006). The 1,4-bis(3-pyridylmethoxy)benzene molecule is centrosymmetric. The planes of two terminal pyridyl groups rotate drastically and make dihedral angles of 66.8 (1) ° with the plane of the central benzene ring.

In the crystal structure, the adjacent 1,4-bis(3-pyridylmethoxy)benzene molecules are linked into two-dimensional supramolecular sheets by intermolecular C—H···N hydrogen bonds (Table 1, Figure 2).

Related literature top

For general background tobridging molecules with pyridyl substituents at the terminal positions, see: McMorran & Steel (1998); Zaman et al. (2005). For details of the synthesis, see: Gao et al. (2004). For a related structure, see: Gao et al. (2006).

Experimental top

The 1,4-bis(3-pyridylmethoxy)benzene was synthesized by the reaction of p-benzenediol and 3-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 three 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 the atomic numbering and displacement ellipsoids at the 30% probability level [symmetry code: (i) -x, 1 - y, -z].
	Fig. 2. A portion of the crystal packing showing the two-dimensional hydrogen bonded (dashed lines) sheet.

1,4-Bis(pyridin-3-ylmethoxy)benzene top

Crystal data top

C₁₈H₁₆N₂O₂	F(000) = 308
M_r = 292.33	D_x = 1.321 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4889 reflections
a = 6.852 (5) Å	θ = 3.7–27.5°
b = 5.688 (3) Å	µ = 0.09 mm⁻¹
c = 18.861 (12) Å	T = 291 K
β = 90.60 (3)°	Block, colourless
V = 735.0 (8) Å³	0.22 × 0.20 × 0.19 mm
Z = 2

Data collection top

Rigaku RAXIS-RAPID diffractometer	1684 independent reflections
Radiation source: fine-focus sealed tube	1213 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scan	θ_max = 27.5°, θ_min = 3.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
T_min = 0.981, T_max = 0.984	k = −6→7
6855 measured reflections	l = −24→24

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0606P)² + 0.0635P] where P = (F_o² + 2F_c²)/3
1684 reflections	(Δ/σ)_max < 0.001
100 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₂	V = 735.0 (8) Å³
M_r = 292.33	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.852 (5) Å	µ = 0.09 mm⁻¹
b = 5.688 (3) Å	T = 291 K
c = 18.861 (12) Å	0.22 × 0.20 × 0.19 mm
β = 90.60 (3)°

Data collection top

Rigaku RAXIS-RAPID diffractometer	1684 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1213 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.984	R_int = 0.030
6855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.09	Δρ_max = 0.24 e Å⁻³
1684 reflections	Δρ_min = −0.14 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	0.8460 (2)	−0.0288 (3)	0.20865 (8)	0.0485 (4)
H1	0.9650	−0.0611	0.2307	0.058*
C2	0.7721 (2)	−0.1906 (3)	0.16191 (8)	0.0530 (4)
H2	0.8404	−0.3281	0.1524	0.064*
C3	0.5951 (2)	−0.1469 (3)	0.12921 (8)	0.0484 (4)
H3	0.5422	−0.2545	0.0972	0.058*
C4	0.49744 (18)	0.0588 (2)	0.14460 (7)	0.0367 (3)
C5	0.5857 (2)	0.2119 (3)	0.19208 (7)	0.0428 (4)
H5	0.5213	0.3517	0.2022	0.051*
C6	0.30072 (19)	0.1158 (3)	0.11378 (7)	0.0433 (4)
H6A	0.2437	−0.0233	0.0922	0.052*
H6B	0.2144	0.1704	0.1507	0.052*
C7	0.15874 (17)	0.3913 (2)	0.03246 (7)	0.0368 (3)
C8	−0.02824 (18)	0.3034 (3)	0.04198 (7)	0.0408 (3)
H8	−0.0477	0.1710	0.0700	0.049*
C9	−0.18583 (18)	0.4142 (3)	0.00955 (7)	0.0408 (3)
H9	−0.3112	0.3563	0.0163	0.049*
N1	0.75686 (17)	0.1729 (2)	0.22431 (7)	0.0510 (4)
O1	0.32526 (13)	0.29466 (19)	0.06180 (5)	0.0509 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0308 (7)	0.0572 (9)	0.0571 (9)	0.0002 (6)	−0.0101 (6)	0.0171 (7)
C2	0.0439 (9)	0.0449 (8)	0.0700 (10)	0.0117 (7)	−0.0063 (7)	0.0064 (8)
C3	0.0487 (8)	0.0432 (8)	0.0532 (8)	0.0035 (7)	−0.0108 (6)	−0.0038 (7)
C4	0.0308 (6)	0.0395 (7)	0.0396 (7)	−0.0005 (5)	−0.0056 (5)	0.0083 (6)
C5	0.0371 (7)	0.0388 (7)	0.0525 (8)	0.0016 (6)	−0.0069 (6)	0.0008 (6)
C6	0.0334 (7)	0.0482 (8)	0.0482 (8)	−0.0010 (6)	−0.0093 (6)	0.0109 (6)
C7	0.0264 (6)	0.0465 (8)	0.0374 (6)	0.0056 (5)	−0.0046 (5)	0.0038 (6)
C8	0.0308 (7)	0.0475 (8)	0.0438 (7)	−0.0007 (6)	−0.0045 (5)	0.0111 (6)
C9	0.0250 (6)	0.0530 (8)	0.0444 (7)	−0.0016 (6)	−0.0030 (5)	0.0073 (6)
N1	0.0394 (7)	0.0538 (8)	0.0596 (8)	−0.0056 (6)	−0.0145 (6)	0.0004 (6)
O1	0.0269 (5)	0.0683 (7)	0.0573 (6)	0.0058 (4)	−0.0048 (4)	0.0267 (5)

Geometric parameters (Å, º) top

C1—N1	1.334 (2)	C6—O1	1.4239 (17)
C1—C2	1.368 (2)	C6—H6A	0.9700
C1—H1	0.9300	C6—H6B	0.9700
C2—C3	1.378 (2)	C7—C9ⁱ	1.374 (2)
C2—H2	0.9300	C7—O1	1.3773 (17)
C3—C4	1.380 (2)	C7—C8	1.389 (2)
C3—H3	0.9300	C8—C9	1.3869 (19)
C4—C5	1.3839 (19)	C8—H8	0.9300
C4—C6	1.4979 (19)	C9—C7ⁱ	1.374 (2)
C5—N1	1.3336 (19)	C9—H9	0.9300
C5—H5	0.9300

N1—C1—C2	123.64 (13)	O1—C6—H6A	110.1
N1—C1—H1	118.2	C4—C6—H6A	110.1
C2—C1—H1	118.2	O1—C6—H6B	110.1
C1—C2—C3	119.03 (14)	C4—C6—H6B	110.1
C1—C2—H2	120.5	H6A—C6—H6B	108.4
C3—C2—H2	120.5	C9ⁱ—C7—O1	115.88 (11)
C2—C3—C4	119.04 (14)	C9ⁱ—C7—C8	119.64 (12)
C2—C3—H3	120.5	O1—C7—C8	124.47 (13)
C4—C3—H3	120.5	C9—C8—C7	119.64 (14)
C3—C4—C5	117.37 (13)	C9—C8—H8	120.2
C3—C4—C6	122.56 (13)	C7—C8—H8	120.2
C5—C4—C6	120.04 (13)	C7ⁱ—C9—C8	120.71 (12)
N1—C5—C4	124.50 (14)	C7ⁱ—C9—H9	119.6
N1—C5—H5	117.7	C8—C9—H9	119.6
C4—C5—H5	117.7	C5—N1—C1	116.41 (13)
O1—C6—C4	108.04 (11)	C7—O1—C6	117.28 (10)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1ⁱⁱ	0.93	2.57	3.437 (3)	155

Symmetry code: (ii) −x+2, y−1/2, −z+1/2.

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)	6.852 (5), 5.688 (3), 18.861 (12)
β (°)	90.60 (3)
V (Å³)	735.0 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.20 × 0.19

Data collection
Diffractometer	Rigaku RAXIS-RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.981, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	6855, 1684, 1213
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 1.09
No. of reflections	1684
No. of parameters	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.14

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
C1—H1···N1ⁱ	0.93	2.57	3.437 (3)	155.2

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Acknowledgements

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

References

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