7-Chloro-4-[(E)-2-(3,4,5-trimeth­oxy­benzyl­idene)hydrazin-1-yl]quinoline

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

doi:10.1107/S1600536812012755

. 2012 Mar 28;68(Pt 4):o1214–o1215. doi: 10.1107/S1600536812012755

7-Chloro-4-[(E)-2-(3,4,5-trimethoxybenzylidene)hydrazin-1-yl]quinoline

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

PMCID: PMC3344149 PMID: 22606152

Abstract

In the title compound, C₁₉H₁₈ClN₃O₃, the r.m.s. deviation through the 23 non-H and non-methoxy atoms is 0.088 Å, indicating a planar molecule with the exception of the methoxy groups. One methoxy group, surrounded on either side by the other methoxy groups, is almost normal to the benzene ring to which it is connected [C—O—C_ar—C_ar torsion angle = 81.64 (15)°]. In the crystal, N—H⋯O, C—H⋯O and π–π interactions [between quinoline residues; centroid–centroid distance = 3.4375 (8) Å] link molecules into a three-dimensional architecture.

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. (2012 ▶). For related structures, see: Howie et al. (2010 ▶); de Souza et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C₁₉H₁₈ClN₃O₃
M _r = 371.81
Orthorhombic,
a = 7.6338 (2) Å
b = 15.5335 (4) Å
c = 28.7960 (7) Å
V = 3414.62 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 120 K
0.45 × 0.40 × 0.30 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
22673 measured reflections
3899 independent reflections
3353 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.101
S = 1.02
3899 reflections
241 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 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/S1600536812012755/bt5858sup1.cif

e-68-o1214-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012755/bt5858Isup2.hkl

e-68-o1214-Isup2.hkl^{(187.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012755/bt5858Isup3.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⋯O3ⁱ	0.87 (1)	2.53 (2)	3.0349 (15)	118 (1)
C19—H19B⋯N1ⁱⁱ	0.98	2.48	3.3602 (18)	149

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

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 title compound, (I), was investigated as part of on-going crystallographic investigations of arylaldehyde 7-chloroquinoline-4-hydrazone species (Howie et al., 2010; de Souza et al., 2010; de Souza et al., 2012). The structural studies complement biological studies which show these hydrazones to possess a wide range of pharmacological activities such as anti-tubercular (Candea et al., 2009) and anti-tumour (Montenegro et al., 2012) activities, which are ascribed to the presence of the quinoline nucleus (de Souza et al., 2009).

In (I), Fig. 1, with the exception of two of the methyoxy groups, the molecule is planar. The r.m.s. deviation through the 23 non-hydrogen and non-methoxy atoms is 0.0879 Å. The maximum deviations from this plane are 0.1219 (11) Å for the N2 atom and -0.1498 (11) for the C14 atom. The terminal carbon atoms, C17–C19, of the methoxy groups lie -0.0840 (17), 0.7910 (16) and -0.3504 (19) Å, respectively, out of the least-squares plane, indicating that the central methoxy group is almost orthogonal to the benzene ring to which it is connected with the C18—O2—C14—C13 torsion angle being 81.64 (15)°. The conformation about the N3═C10 bond [1.2829 (17) Å] is E.

In the crystal packing, weak N—H···O hydrogen bonds along with C—H···O interactions, Table 1, and π—π interactions between symmetry related quinolinyl residues [centroid···centroid distance = 3.4375 (8) Å for symmetry operation -1/2 + x, y, 1/2 - z] link molecules into a three-dimensional architecture. Globally, molecules stack along the c axis with alternating layers of quinolinyl and trimethoxybenzene residues, Fig. 2.

Experimental

The compound was prepared from 7-chloro-4-quinolinylhydrazone and 3,4,5-trimethoxybenzaldehyde (Montenegro et al., 2012) and was recrystallized from an EtOCH₂CH₂OH solution of the compound.