1,4-Bis(2-pyridylmethyl­eneamino­meth­yl)benzene

Li, C.; Sun, F.-A.; He, M.-Y.; Xu, H.; Chen, Q.

doi:10.1107/S1600536809000646

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o286

doi:10.1107/S1600536809000646

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1,4-Bis(2-pyridylmethyleneaminomethyl)benzene

Chao Li,^a Fu-An Sun,^a Ming-Yang He,^a Huan Xu ^a and Qun Chen ^a ^*

^aKey Laboratory of Fine Petro-Chemical technology, Jiangsu Polytechnic University, Changzhou 213164, People's Republic of China
^*Correspondence e-mail: chenqunjpu@yahoo.com

(Received 1 December 2008; accepted 7 January 2009; online 10 January 2009)

The asymmetric unit of the centrosymmetric title compound, C₂₀H₁₈N₄, contains one half-molecule. The pyridine and benzene rings are oriented at a dihedral angle of 77.21 (7)°.

Related literature

For general background, see: Barboiu et al. (2006 ); Keegan et al. (2002 ); Yue et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₈N₄
M_r = 314.38
Triclinic, $[P \overline 1]$
a = 4.527 (3) Å
b = 10.117 (6) Å
c = 10.456 (6) Å
α = 61.086 (7)°
β = 88.543 (8)°
γ = 82.242 (8)°
V = 414.9 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 (2) K
0.32 × 0.30 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.976, T_max = 0.990
2909 measured reflections
1449 independent reflections
1250 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.105
S = 1.01
1449 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000646/hk2592sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000646/hk2592Isup2.hkl

checkCIF report

Comment top

Bipyridyl-type bidentate Schiff base ligands have been utilized intensively to assemble various coordination polymers with interesting topologies and fascinating structural diversities (Barboiu et al., 2006; Keegan et al., 2002; Yue et al., 2004). We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains one-half of the centrosymmetric molecule, where the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N1/C1-C5) and B (C8-C10/C8A-C10A) are, of course, planar, and they are oriented at a dihedral angle of 77.21 (7)° [symmetry code: (A) 1 - x, 1 - y, 1 - z].

Related literature top

For general background, see: Barboiu et al. (2006); Keegan et al. (2002); Yue et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared from the condensation reaction between pyridine-2-carboxaldehyde (100 mmol) and 1,4-benzenedimethanamine (50 mmol) in tetrahydrofuran (yield; 83%). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code: (A) 1 - x, 1 - y, 1 - z].

1,4-Bis(2-pyridylmethyleneaminomethyl)benzene top

Crystal data top

C₂₀H₁₈N₄	Z = 1
M_r = 314.38	F(000) = 166
Triclinic, P1	D_x = 1.258 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.527 (3) Å	Cell parameters from 1582 reflections
b = 10.117 (6) Å	θ = 2.2–27.0°
c = 10.456 (6) Å	µ = 0.08 mm⁻¹
α = 61.086 (7)°	T = 296 K
β = 88.543 (8)°	Block, colorless
γ = 82.242 (8)°	0.32 × 0.30 × 0.23 mm
V = 414.9 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	1449 independent reflections
Radiation source: fine-focus sealed tube	1250 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −5→5
T_min = 0.976, T_max = 0.990	k = −12→12
2909 measured reflections	l = −12→11

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0582P)² + 0.0501P] where P = (F_o² + 2F_c²)/3
1449 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₁₈N₄	γ = 82.242 (8)°
M_r = 314.38	V = 414.9 (4) Å³
Triclinic, P1	Z = 1
a = 4.527 (3) Å	Mo Kα radiation
b = 10.117 (6) Å	µ = 0.08 mm⁻¹
c = 10.456 (6) Å	T = 296 K
α = 61.086 (7)°	0.32 × 0.30 × 0.23 mm
β = 88.543 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1449 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	1250 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.990	R_int = 0.021
2909 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.01	Δρ_max = 0.14 e Å⁻³
1449 reflections	Δρ_min = −0.18 e Å⁻³
109 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
N1	0.8015 (3)	0.26368 (14)	1.18773 (13)	0.0628 (3)
N2	0.4321 (2)	0.26607 (12)	0.89307 (11)	0.0516 (3)
C1	0.7265 (3)	0.20335 (14)	1.10637 (13)	0.0477 (3)
C2	0.8567 (3)	0.06149 (15)	1.12895 (14)	0.0536 (3)
H2	0.7948	0.0215	1.0722	0.064*
C3	1.0786 (3)	−0.01952 (17)	1.23630 (16)	0.0622 (4)
H3	1.1727	−0.1140	1.2519	0.075*
C4	1.1584 (4)	0.04142 (19)	1.31980 (16)	0.0673 (4)
H4	1.3071	−0.0110	1.3937	0.081*
C5	1.0143 (4)	0.18146 (19)	1.29230 (17)	0.0714 (5)
H5	1.0687	0.2215	1.3503	0.086*
C6	0.4970 (3)	0.29926 (14)	0.98916 (14)	0.0497 (3)
H6	0.3968	0.3873	0.9862	0.060*
C7	0.2103 (3)	0.37330 (16)	0.77804 (14)	0.0560 (4)
H7A	0.1281	0.4543	0.7986	0.067*
H7B	0.0484	0.3210	0.7748	0.067*
C8	0.3559 (3)	0.43975 (14)	0.63283 (13)	0.0470 (3)
C9	0.3629 (3)	0.37288 (15)	0.54431 (14)	0.0541 (3)
H9	0.2705	0.2866	0.5733	0.065*
C10	0.4953 (3)	0.56793 (15)	0.58621 (14)	0.0544 (4)
H10	0.4935	0.6150	0.6438	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0703 (8)	0.0659 (7)	0.0620 (7)	−0.0068 (6)	−0.0016 (6)	−0.0391 (6)
N2	0.0562 (7)	0.0502 (6)	0.0452 (6)	−0.0045 (5)	0.0029 (5)	−0.0215 (5)
C1	0.0499 (7)	0.0519 (7)	0.0441 (7)	−0.0121 (6)	0.0107 (5)	−0.0246 (6)
C2	0.0571 (8)	0.0527 (7)	0.0524 (7)	−0.0080 (6)	0.0060 (6)	−0.0268 (6)
C3	0.0614 (9)	0.0552 (8)	0.0598 (8)	−0.0025 (6)	0.0032 (7)	−0.0214 (7)
C4	0.0614 (9)	0.0776 (10)	0.0520 (8)	−0.0078 (8)	−0.0027 (7)	−0.0231 (8)
C5	0.0784 (11)	0.0846 (11)	0.0626 (9)	−0.0120 (9)	−0.0046 (8)	−0.0441 (9)
C6	0.0521 (7)	0.0461 (7)	0.0512 (7)	−0.0057 (5)	0.0079 (6)	−0.0245 (6)
C7	0.0507 (8)	0.0607 (8)	0.0542 (8)	−0.0029 (6)	0.0009 (6)	−0.0271 (7)
C8	0.0393 (6)	0.0488 (7)	0.0470 (7)	0.0033 (5)	−0.0071 (5)	−0.0206 (6)
C9	0.0563 (8)	0.0498 (7)	0.0571 (8)	−0.0099 (6)	−0.0004 (6)	−0.0258 (6)
C10	0.0593 (8)	0.0566 (8)	0.0539 (8)	−0.0048 (6)	−0.0020 (6)	−0.0326 (6)

Geometric parameters (Å, º) top

N1—C1	1.3358 (17)	C6—C1	1.472 (2)
N1—C5	1.332 (2)	C6—H6	0.9300
N2—C6	1.2555 (17)	C7—H7A	0.9700
N2—C7	1.4620 (18)	C7—H7B	0.9700
C1—C2	1.383 (2)	C8—C7	1.5078 (19)
C2—C3	1.373 (2)	C8—C9	1.3832 (19)
C2—H2	0.9300	C8—C10	1.383 (2)
C3—C4	1.367 (2)	C9—C10ⁱ	1.379 (2)
C3—H3	0.9300	C9—H9	0.9300
C4—C5	1.372 (2)	C10—C9ⁱ	1.379 (2)
C4—H4	0.9300	C10—H10	0.9300
C5—H5	0.9300

C5—N1—C1	116.79 (13)	N2—C6—H6	118.9
C6—N2—C7	117.39 (12)	C1—C6—H6	118.9
N1—C1—C2	122.69 (13)	N2—C7—C8	109.34 (11)
N1—C1—C6	115.30 (12)	N2—C7—H7A	109.8
C2—C1—C6	122.01 (12)	C8—C7—H7A	109.8
C3—C2—C1	119.09 (13)	N2—C7—H7B	109.8
C3—C2—H2	120.5	C8—C7—H7B	109.8
C1—C2—H2	120.5	H7A—C7—H7B	108.3
C4—C3—C2	118.73 (14)	C9—C8—C7	121.61 (12)
C4—C3—H3	120.6	C10—C8—C7	120.48 (11)
C2—C3—H3	120.6	C10ⁱ—C9—C8	121.07 (13)
C3—C4—C5	118.57 (14)	C10—C8—C9	117.88 (12)
C3—C4—H4	120.7	C10ⁱ—C9—H9	119.5
C5—C4—H4	120.7	C8—C9—H9	119.5
N1—C5—C4	124.10 (14)	C9ⁱ—C10—C8	121.05 (12)
N1—C5—H5	117.9	C9ⁱ—C10—H10	119.5
C4—C5—H5	117.9	C8—C10—H10	119.5
N2—C6—C1	122.13 (12)

C5—N1—C1—C2	1.0 (2)	C3—C4—C5—N1	−0.7 (2)
C5—N1—C1—C6	−178.28 (12)	N2—C6—C1—N1	170.79 (11)
C1—N1—C5—C4	0.3 (2)	N2—C6—C1—C2	−8.52 (19)
C7—N2—C6—C1	−177.26 (11)	C9—C8—C7—N2	90.82 (14)
C6—N2—C7—C8	115.21 (13)	C10—C8—C7—N2	−87.19 (15)
N1—C1—C2—C3	−2.0 (2)	C7—C8—C9—C10ⁱ	−178.00 (12)
C6—C1—C2—C3	177.27 (11)	C10—C8—C9—C10ⁱ	0.1 (2)
C1—C2—C3—C4	1.6 (2)	C7—C8—C10—C9ⁱ	178.03 (12)
C2—C3—C4—C5	−0.3 (2)	C9—C8—C10—C9ⁱ	−0.1 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₄
M_r	314.38
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	4.527 (3), 10.117 (6), 10.456 (6)
α, β, γ (°)	61.086 (7), 88.543 (8), 82.242 (8)
V (Å³)	414.9 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.30 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.976, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	2909, 1449, 1250
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.105, 1.01
No. of reflections	1449
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Center for Testing and Analysis at Yangzhou University for support.

References

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