Crystal structure of N 1,N 1-diethyl-N 4-[(quinolin-2-yl)methyl­idene]benzene-1,4-di­amine

Md Serajul Haque Faizi; Nazia Siddiqui; Saleem Javed

doi:10.1107/S2056989014027108

. 2015 Jan 1;71(Pt 1):o49–o50. doi: 10.1107/S2056989014027108

Crystal structure of N ¹,N ¹-diethyl-N ⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine

Md Serajul Haque Faizi ^a, Nazia Siddiqui ^a, Saleem Javed ^b,^*

PMCID: PMC4331901 PMID: 25705502

Abstract

The title compound, C₂₀H₂₁N₃, is non-planar with a dihedral angle between the planes of the quinoline and phenylenediamine rings of 9.40 (4)°. In the crystal, molecules are connected by C—H⋯π interactions, generating a chain extending along the a-axis direction. Weak C—H⋯π interactions also occur.

Keywords: crystal structure; benzene-1,4-diamine; quinoline; C—H⋯π interactions; quinolinyl-containing Schiff bases

Related literature

For applications of quinolinyl-containing Schiff bases, see: Das et al. (2013 ▸); Jursic et al. (2002 ▸); Motswainyana et al. (2013 ▸); Song et al. (2011 ▸). The present work is part of an ongoing structural study of Schiff base–metal complexes, see: Faizi & Hussain (2014 ▸); Faizi & Sen (2014 ▸); Faizi et al. (2014 ▸). For related Schiff bases and their applications, see: Gonzalez et al. (2012 ▸); Patra & Goldberg (2003 ▸). graphic file with name e-71-00o49-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₁N₃
M _r = 303.40
Orthorhombic,
a = 20.354 (5) Å
b = 7.534 (5) Å
c = 21.801 (5) Å
V = 3343 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.27 × 0.21 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▸) T _min = 0.981, T _max = 0.989
14928 measured reflections
2937 independent reflections
1912 reflections with I > 2σ(I)
R _int = 0.146

Refinement

R[F ² > 2σ(F ²)] = 0.084
wR(F ²) = 0.195
S = 1.09
2937 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2003 ▸); cell refinement: SAINT (Bruker, 2003 ▸); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▸); molecular graphics: DIAMOND (Brandenberg & Putz, 2005 ▸); software used to prepare material for publication: DIAMOND.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027108/hg5416sup1.cif

e-71-00o49-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027108/hg5416Isup2.hkl

e-71-00o49-Isup2.hkl^{(141.3KB, hkl)}

Click here for additional data file.^{(6.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989014027108/hg5416Isup3.cml

Click here for additional data file.^{(1MB, tif)}

. DOI: 10.1107/S2056989014027108/hg5416fig1.tif

The molecular conformation and atom-numbering scheme for the title compound, with non-H atoms drawn as 40% probability displacement ellipsoids.

Click here for additional data file.^{(1.5MB, tif)}

a . DOI: 10.1107/S2056989014027108/hg5416fig2.tif

The molecular packing viewed along the a direction.

CCDC reference: 1038674

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6C9, C1C16 and C11C16 rings, respectively.

DHA	DH	HA	D A	DHA
C5H5Cg2ⁱ	0.93	2.99	3.705(5)	135
C7H7Cg1ⁱ	0.93	2.90	3.612(5)	135
C13H13Cg3ⁱⁱ	0.93	2.84	3.588(5)	138
C15H15Cg2ⁱⁱⁱ	0.93	2.89	3.686(5)	145
C18H18A Cg1ⁱⁱⁱ	0.96	2.95	3.625(5)	128

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors are grateful to the Department of Chemistry, IIT Kanpur, Kanpur 208 016, India, for the X-ray data collection and to Musheer Ahmad for valuable discussions.

supplementary crystallographic information

S1. Comment

Quinoline derivatives of Schiff bases are important building blocks of many important compounds widely used in biological applications such as antioxidative and anticancer and fluorescent probe agents in industry and in coordination chemistry (Motswainyana et al., 2013; Das et al., 2013; Song et al., 2011; Jursic et al., 2002). The present work is part of an ongoing structural study of Schiff base metal complexes (Faizi & Hussain, 2014; Faizi & Sen, 2014; Faizi et al. 2014) and we report here the structure of N¹,N¹-diethyl-N⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine (DQMBD). There are very few examples similar to title compound and their metal complex have been reported in the literature (Patra & Goldberg 2003; Gonzalez et al., 2012). The synthesis of DQMBD by condensation of 2-quinolinecarboxaldehyde and N¹,N¹-diethyl-p-phenylenediamine has not previously been reported. In the title compound (Fig. 1) DQMBD has non planar structure, the dihedral angle between the quinolinyl and pphenylenediamine rings is 9.40 (4)°. In the crystal, molecules are connected by C—H···π, generating a chain extending along the a axis direction. In the crystal molecules are connected by C—H···π, giving an overall two-dimensional layered structure lying parallel to (100) is given in Fig. 2.

S2. Experimental

100 mg (1 mmol) of N¹,N¹-diethyl-p-phenylenediamine were dissolved in 10 ml of absolute ethanol. To this solution, 96 mg (1 mmol) of 2-quinolinecarboxaldehyde in 5 ml of absolute ethanol was dropwisely added under stirring. Then, this mixture was stirred for 10 min, two drops of glacial acetic acid were then added and the mixture was further refluxed for 2h. The resulting yellow precipitate was recovered by filtration, washed several times with a small portions of EtOH and then with diethyl ether to give 160 mg (88%) of N¹,N¹-diethyl-N⁴-(quinolin-2-ylmethylene)benzene-1,4-diamine (DQMBD). The crystal of the title compound suitable for X-ray analysis was obtained within 4 days by slow evaporation of the EtOH solvent.