7-Chloro-4-[(E)-2-(2,5-dimeth­oxy­benzyl­idene)hydrazin-1-yl]quinoline

Marcus V N de Souza; Marcelle de Lima Ferreira; Solange M S V Wardell; Edward R T Tiekink; James L Wardell

doi:10.1107/S1600536812012871

. 2012 Mar 31;68(Pt 4):o1244–o1245. doi: 10.1107/S1600536812012871

7-Chloro-4-[(E)-2-(2,5-dimethoxybenzylidene)hydrazin-1-yl]quinoline

Marcus V N de Souza ^a, Marcelle de Lima Ferreira ^a, Solange M S V Wardell ^b, Edward R T Tiekink ^c,^*, James L Wardell ^d,^‡

PMCID: PMC3344174 PMID: 22606177

Abstract

In the nearly planar title compound (r.m.s. deviation for the 24 non-H atoms = 0.064 Å), C₁₈H₁₆ClN₃O₂, the conformation about the N=C bond is E. Supramolecular chains propagated by glide symmetry along [001] are found in the crystal packing. These are sustained by N—H⋯N hydrogen bonds with the quinoline N atom being the acceptor. The chains are connected into a three-dimensional architecture by π–π interactions involving all three aromatic rings [centroid–centroid distances = 3.5650 (9)–3.6264 (9) Å].

Related literature

For the biological activity, including anti-tubercular and anti-tumour activity, of compounds containing the quinolinyl nucleus, see: de Souza et al. (2009 ▶); Candea et al. (2009 ▶); Montenegro et al. (2011 ▶, 2012 ▶). For related structures, see: Howie et al. (2010 ▶); de Souza et al. (2010 ▶); de Lima Ferreira et al. (2010 ▶). For the synthesis, see: Montenegro et al. (2012 ▶).

Experimental

Crystal data

C₁₈H₁₆ClN₃O₂
M _r = 341.79
Monoclinic,
a = 10.5183 (2) Å
b = 12.9132 (3) Å
c = 12.9861 (2) Å
β = 112.723 (2)°
V = 1626.93 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 120 K
0.32 × 0.20 × 0.15 mm

Data collection

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.652, T _max = 0.746
20405 measured reflections
3723 independent reflections
3067 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.107
S = 1.03
3723 reflections
222 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012871/xu5494sup1.cif

e-68-o1244-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012871/xu5494Isup2.hkl

e-68-o1244-Isup2.hkl^{(178.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012871/xu5494Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯N1ⁱ	0.88 (1)	2.19 (1)	3.0572 (17)	167 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR/MOHE/SC/12) is gratefully acknowledged.

supplementary crystallographic information

Comment

The quinoline nucleus is an important moiety found in various synthetic and natural products with a wide range of pharmacological activities (de Souza et al., 2009), including anti-tubercular (Candea et al., 2009) and anti-tumour (Montenegro et al., 2012) activities. Among the derivatives studied have been arylaldehyde 7-chloroquinoline-4-hydrazones (Candea et al., 2009; Montenegro et al., 2011). Some crystal structures of the these hydrazones, including related methoxy-substituted derivatives have been reported (Howie et al., 2010; de Souza et al., 2010; de Lima Ferreira et al., 2010). We now wish to report the crystal structure of the title compound, (I).

In (I), Fig. 1, the entire molecule is planar with the r.m.s. deviation of all 24 non-hydrogen atoms being 0.064 Å. The maximum deviations from the least-squares plane are 0.108 (2) for the C5 atom and -0.165 (1) Å for the Cl1 atom. The conformation about the N3═C10 bond [1.2834 (18) Å] is E.

The most prominent feature of the crystal packing is the formation of supramolecular chains via N—H···N hydrogen bonds with the quinolinyl-N atom being the acceptor, Table 1. The chains a propagated by glide symmetry along the c axis, Fig. 2. Molecules are consolidated into a three-dimensional architecture by π—π interactions whereby the dimethoxybenzene ring interacts with both components of the quinolinyl residue along with symmetry related dimethoxybenzene rings [centroid(dimethoxybenzene)···centroid(NC₅)ⁱ; (C₆)ⁱ; (dimethoxybenzene)ⁱⁱ = 3.5650 (9), 3.6264 (9) and 3.5872 (9) Å, with angles of inclination = 2.36 (7) 4.20 (7) and 0° for symmetry operations i: 1 - x, -y, 1 - z and ii: 2 - x, -y, 1 - z]. The π—π interactions between the dimethoxybenzene and quinolinyl residues lead to zigzag layers in the bc plane and the π(dimethoxybenzene)···π(dimethoxybenzene) interactions link these layers along the a axis, Fig. 3.

Experimental

The compound was prepared from 7-chloro-4-quinolinylhydrazone with 2,5-dimethoxybenzaldehyde (Montenegro et al., 2012). The crystals used in the structure determination were grown from an ethanol solution of the compound.