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

Md Serajul Haque Faizi; Ashraf Mashrai; Saleem Garandal; M Shahid

doi:10.1107/S1600536814016006

. 2014 Aug 1;70(Pt 9):o905–o906. doi: 10.1107/S1600536814016006

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

Md Serajul Haque Faizi ^a, Ashraf Mashrai ^b, Saleem Garandal ^c, M Shahid ^b,^*

PMCID: PMC4186095 PMID: 25309245

Abstract

In the title compound, C₂₂H₁₇N₃, the dihedral angles between the central benzene ring and the terminal phenyl ring and quinoline ring system (r.m.s. deviation = 0.027 Å) are 44.72 (7) and 9.02 (4)°, respectively, and the bond-angle sum at the amine N atom is 359.9°. In the crystal, the N—H group is not involved in hydrogen bonding and the molecules are linked by weak C—H⋯π interactions, generating [010] chains.

Keywords: crystal structure, quinoline, C—H⋯π interactions

Related literature

For applications of quinoline-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 ▶). graphic file with name e-70-0o905-scheme1.jpg

Experimental

Crystal data

C₂₂H₁₇N₃
M _r = 323.39
Monoclinic,
a = 17.595 (2) Å
b = 7.3348 (8) Å
c = 12.5712 (18) Å
β = 99.769 (6)°
V = 1598.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.29 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.967, T _max = 0.984
6866 measured reflections
2964 independent reflections
1557 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.105
S = 0.97
2964 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 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, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2006 ▶); software used to prepare material for publication: DIAMOND.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016006/hb7248sup1.cif

e-70-0o905-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016006/hb7248Isup2.hkl

e-70-0o905-Isup2.hkl^{(142.5KB, hkl)}

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

Supporting information file. DOI: 10.1107/S1600536814016006/hb7248Isup3.cml

Click here for additional data file.^{(996.6KB, tif)}

. DOI: 10.1107/S1600536814016006/hb7248fig1.tif

The molecular structure of the title compound, with non-H atoms drawn as 40% probability displacement ellipsoids.

CCDC reference: 1012864

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6–C9, C1–C6 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg3ⁱ	0.93	2.61	3.430 (2)	148
C12—H12⋯Cg1ⁱ	0.93	2.79	3.536 (2)	138
C13—H13⋯Cg2ⁱ	0.93	2.71	3.508 (3)	145

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Department of Chemistry, IIT Kanpur, Kanpur-208016, India, for the data collection and Musheer Ahmad for valuable discussions.

supplementary crystallographic information

S1. Chemical context

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-phenyl-N⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine (PQMBD).

S2. Structural commentary

The synthesis of PQMBD by condensation of 2-quinolinecarboxaldehyde and N-phenyl-p-phenylenediamine has not previously been reported. In the title compound (Fig. 1) PQMBD has non planar structure, the dihedral angle between the quinolinyl and p-phenylenediamine rings is 9.02 (4)° and the dihedral angle between the p-phenylenediamine and N-phenyl rings is 44.72 (7)°. The imine group displays a torsional angle (C9—C10—N2—C11) of 179.20 (2)°.

S3. Supramolecular features

In the crystal, the N—H group is not involved in hydrogen bonding and the molecules are linked by weak C—H···π interactions, generating [010] chains.

S4. Database survey

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).

S5. Synthesis and crystallization

100 mg (1 mmol) of N-phenyl-p-phenylenediamine were dissolved in 10 ml of absolute ethanol. To this solution, 85 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 2 h. The resulting yellow precipitate was recovered by filtration, washed several times with a small portions of EtOH and then with diethyl ether to give 150 mg (88%) of the title compound. Yellow blocks were obtained within 3 days by slow evaporation of the MeOH solvent.

S6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. the N-bound H-atoms were located in difference Fourier maps,and their positions were then held fixed. All H-atoms were positioned geometrically and refined using a riding model with C—H = 0.92–0.93 Å and U_iso(H) = 1.2U_eq(C).