Home The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
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The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2

  • Eric M. Njogu , Bernard Omondi EMAIL logo and Vincent O. Nyamori
Published/Copyright: March 22, 2017

Abstract

C18H22N2, monoclinic, P21/c (no. 14), a = 9.4660(4) Å, b = 9.4043(3) Å, c = 18.0824(7) Å, β = 96.070(2)°, V = 1600.69(11) Å3, Z = 4, Rgt(F) = 0.0426, wRref(F2) = 0.1167, T = 100 K.

CCDC no.:: 1534696

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Yellow plate
Size:0.40 × 0.24 × 0.15 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.7 cm−1
Diffractometer, scan mode:Bruker APEX-II, 0.5° φ and ω
2θmax, completeness:57°, >99%
N(hkl)measured, N(hkl)unique, Rint:34122, 4031, 0.021
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3653
N(param)refined:181
Programs:Bruker programs [1], SHELX [2], WinGX [3]
Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
C10.31520(9)0.29257(9)0.14381(5)0.01553(17)
C20.25647(9)0.42535(9)0.12443(5)0.01756(18)
H20.29140.50890.14960.021*
C30.14600(9)0.43261(10)0.06762(5)0.01904(19)
H30.10720.52340.05430.023*
C40.14660(10)0.19210(10)0.05043(5)0.0210(2)
H40.10770.110.02530.025*
C50.25832(10)0.17357(10)0.10599(5)0.01921(19)
H50.29510.08140.11790.023*
C60.43726(9)0.27549(9)0.20095(5)0.01613(17)
H60.47210.18260.21280.019*
C70.61766(9)0.35502(9)0.28721(5)0.01567(17)
C80.75214(9)0.38690(9)0.26553(5)0.01811(18)
C90.87107(10)0.36395(10)0.31679(6)0.0227(2)
H90.96330.38170.30270.027*
C100.85610(11)0.31564(10)0.38780(6)0.0244(2)
H100.93790.30030.42210.029*
C110.72193(11)0.28954(10)0.40908(5)0.0221(2)
H110.71310.25910.45850.027*
C120.59945(10)0.30700(9)0.35950(5)0.01780(18)
C130.45195(10)0.27883(10)0.38221(5)0.02163(19)
H130.39740.22660.34030.026*
C140.45253(13)0.18524(12)0.45147(6)0.0307(2)
H14A0.35480.17110.46320.046*
H14B0.49520.09290.44210.046*
H14C0.5080.23180.49350.046*
C150.37349(13)0.41896(12)0.39243(7)0.0329(2)
H15A0.27880.39860.4070.049*
H15B0.42720.47570.43120.049*
H15C0.36440.47210.34550.049*
C160.76723(10)0.44096(11)0.18765(5)0.0227(2)
H160.67330.48150.16750.027*
C170.80018(14)0.31810(14)0.13668(6)0.0365(3)
H17A0.80960.35480.08670.055*
H17B0.88920.27240.15650.055*
H17C0.72280.24840.13420.055*
C180.87756(11)0.55959(12)0.18649(6)0.0306(2)
H18A0.8830.59040.13510.046*
H18B0.84980.64020.21610.046*
H18C0.97060.52410.20750.046*
N10.09078(8)0.31848(9)0.03035(4)0.02022(17)
N20.49708(8)0.38144(8)0.23470(4)0.01601(16)

Source of material

The title compound was synthesised by the reaction of 2,6-diisopropylaniline (1.810 g, 10.2 mmol) and 4-pyridinecarboxaldehyde (1.063 g, 9.92 mmol). The reactants were ground together in a Pyrex tube for 5 minutes. The lemon yellow paste obtained, was dried under reduced pressure. The resulting solid was recrystallized from acetone and a crystal yield of 2.510 g (97%) was obtained. Melting point: 105–106 °C.

Experimental details

All hydrogen atoms were placed in idealized positions and refined using a riding model, with H-Uiso(H) = 1.2 − 1.5Ueq(C) and C–H = 0.93 (aromatic), 0.96 (methyl) and 0.98 (methanetriyl) Å.

Discussion

The title compound is a pyridinyl Schiff base obtained from a reaction 2,6-diisopropylaniline and 4-pyridinecarboxaldehyde under solvent-free conditions.

The asymmetric unit of the title compound contains one full molecule. In the unit cell, pairs of molecules have H – π interactions between H atoms from the pyridinyl ring and the phenyl ring with a H – centroid distance of 2.469 Å. The molecular structure of the title compound bears a phenyl imine moiety (from the starting 2,6-diisopropylaniline) and a methyl pyridinyl moiety from the starting 4-pyridinecarboxaldehyde forming the (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene) aniline Schiff base.

The dihedral angle between the two planes containing the phenyl ring/imine N atom and the pyridinyl ring/imine C atom is 79.46(3)°. The C-N(imine) and N(imine)-C(Ph) bond distances are 1.2699(11) and 1.4273(10) Å, respectively. Adjacent molecules form intermolecular contacts involving pyridinyl N and pyridinyl/methyl H atoms leading to formation of infinite supramolecular architecture. More information on synthesis and properties of pyridinyl compounds has been previously reported in the literature [4], [5], [6], [7].

Acknowledgement

We acknowledge the National Research Foundation and University of KwaZulu-Natal, South Africa for financial support for Eric N Njogu.

References

1 Bruker. APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, Wisconsin, USA, (2009).Search in Google Scholar

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3 Farrugia, L. J.: WinGX and ORTEP for Windows. Appl. Crystallogr. 45 (2012) 849–854.10.1107/S0021889812029111Search in Google Scholar

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Received: 2016-11-18
Accepted: 2017-2-24
Published Online: 2017-3-22
Published in Print: 2017-5-24

©2017 Eric M. Njogu et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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