7-Chloro-4-[(E)-2-(2-methoxy­benzyl­idene)hydrazin-1-yl]quinoline monohydrate

Marcus V N de Souza; R Alan Howie; Edward R T Tiekink; James L Wardell; Solange M S V Wardell; Carlos R Kaiser

doi:10.1107/S1600536810006586

. 2010 Feb 27;66(Pt 3):o698–o699. doi: 10.1107/S1600536810006586

7-Chloro-4-[(E)-2-(2-methoxybenzylidene)hydrazin-1-yl]quinoline monohydrate

Marcus V N de Souza ^a, R Alan Howie ^b, Edward R T Tiekink ^c,^*, James L Wardell ^d,^‡, Solange M S V Wardell ^e, Carlos R Kaiser ^f

PMCID: PMC2983501 PMID: 21580438

Abstract

In the title hydrate, C₁₇H₁₄ClN₃O·H₂O, the dihedral angle between the quinoline fused-ring system and the benzene ring is 13.4 (2)° and the conformation about the C=N bond is E. In the crystal, N_h—H⋯O_w and O_w—H⋯N_q (h = hydrozone, w = water and q = quinoline) hydrogen bonds generate a two-dimenstional network in the ac plane. A weak C—H⋯O interaction helps to consolidate the packing.

Related literature

For background to the pharmacological activity of quinoline derivatives, see: Warshakoon et al. (2006 ▶). For recent studies into quinoline-based anti-malarials, see: Andrade et al. (2007 ▶); de Souza et al. (2005 ▶). For related structures, see: Kaiser et al. (2009 ▶); de Souza et al. (2009 ▶, 2010 ▶). For the structure of the isomeric 2-methoxy structure, see: de Lima Ferreira et al. (2010 ▶).

Experimental

Crystal data

C₁₇H₁₄ClN₃O·H₂O
M _r = 329.78
Monoclinic,
a = 3.9202 (2) Å
b = 24.5084 (17) Å
c = 16.1212 (11) Å
β = 91.639 (4)°
V = 1548.26 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 K
0.62 × 0.03 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.735, T _max = 0.995
11507 measured reflections
2716 independent reflections
1769 reflections with I > 2σ(I)
R _int = 0.096

Refinement

R[F ² > 2σ(F ²)] = 0.093
wR(F ²) = 0.260
S = 1.04
2716 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.45 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 datablocks global, I. DOI: 10.1107/S1600536810006586/hb5340sup1.cif

e-66-0o698-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006586/hb5340Isup2.hkl

e-66-0o698-Isup2.hkl^{(130.6KB, hkl)}

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⋯O1W	0.88	2.08	2.928 (7)	161
O1W—H1W⋯N1ⁱ	0.81 (9)	2.30 (9)	3.030 (8)	150 (8)
O1W—H2W⋯N1ⁱⁱ	0.82 (9)	2.03 (9)	2.820 (7)	163 (8)
C5—H5⋯O1W	0.95	2.43	3.358 (8)	166

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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).

supplementary crystallographic information

Comment

Quinoline derivatives are known to display pharmacological potential (Warshakoon et al., 2006) and are being investigated for their anti-malarial activity (Andrade et al. 2007; de Souza et al., 2005). Structural studies on quinoline derivatives augment the biological investigations (Kaiser et al., 2009; de Souza et al., 2009; de Souza et al., 2010; de Lima Ferreira et al., 2010) and as a part of these studies, the crystal structure of the title hydrate, (I), was investigated.

The most significant twist in the quinoline molecule of (I), Fig. 1, occurs around the C10–C11 bond as seen in the N3–C10–C11–C16 torsion angle of 6.9 (9) °. This accounts for the dihedral angle of 13.4 (2) ° formed between the quinoline fused-ring system and the benzene ring. The conformation about the C10═N3 bond [1.282 (8) Å] is E. The crystal packing is stabilised by a variety of hydrogen bonding interactions, Table 1. The water molecule accepts a hydrogen bond from the hydrazone-N2 atom and bridges two symmetry related molecules by forming donor interactions with quinoline-N1 atoms; the water-O atom also participates in a C–H···O contact, Table 1. The result of the hydrogen bonding is the formation of a 2-D supramolecular array in the ac plane, Fig. 2, and these stack along the b axis, Fig. 3.

Experimental

A solution of 7-chloro-4-quinolinylhydrazine(0.2 g, 1.03 mmol) and 2-methoxybenzaldehyde (1.2 mmol) in EtOH (5 ml) was maintained at room temperature overnight and rotary evaporated. The solid residue, was washed with cold Et₂O (3 x 10 ml) and recrystallised from EtOH; m.pt. 459-461 K, yield 82%. The sample for the X-ray study was slowly grown from moist EtOH and was found to be the monohydrate. MS/ESI: [M—H]: 310.8. IR νmax (cm-1; KBr disc): 3190 (N—H), 1578 (C=N).