4-Chloro­benzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone monohydrate

Wan-Sin Loh; Hoong-Kun Fun; Reshma Kayarmar; S Viveka; G K Nagaraja

doi:10.1107/S1600536811001577

. 2011 Jan 15;67(Pt 2):o407–o408. doi: 10.1107/S1600536811001577

4-Chlorobenzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone monohydrate

Wan-Sin Loh ^a,^‡, Hoong-Kun Fun ^a,^*,^§, Reshma Kayarmar ^b, S Viveka ^b, G K Nagaraja ^b

PMCID: PMC3051724 PMID: 21523079

Abstract

In the title compound, C₂₁H₂₀ClN₅·H₂O, the 1H-imidazo[4,5-c]quinoline ring is approximately planar, with a maximum deviation of 0.0795 (7) Å, and it forms a dihedral angle of 7.65 (3)° with the chlorophenyl ring. In the crystal, the components are linked into chains along the a axis via intermolecular N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds. One of the H atoms of the water molecule is disordered over two positions with a site-occupancy ratio of 0.80 (4):0.20 (4).

Related literature

For background to quinolines and their microbial activity, see: El-Subbagh et al. (2000 ▶); Atwell et al. (1989 ▶); Kuo et al. (1993 ▶); Xia et al. (1998 ▶). For the biological activity of Schiff base hydrazones, see: Colins & Lyne (1970 ▶); Ochiai (1977 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Loh et al. (2011a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₁H₂₀ClN₅·H₂O
M _r = 395.89
Monoclinic,
a = 10.4117 (3) Å
b = 18.2365 (6) Å
c = 11.9019 (3) Å
β = 117.809 (2)°
V = 1998.85 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.49 × 0.45 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.904, T _max = 0.963
39468 measured reflections
10411 independent reflections
8351 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.135
S = 1.04
10411 reflections
260 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.19 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001577/is2658sup1.cif

e-67-0o407-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001577/is2658Isup2.hkl

e-67-0o407-Isup2.hkl^{(509.1KB, 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
N4—H1N4⋯O1Wⁱ	0.874 (19)	2.559 (18)	3.2789 (13)	140.2 (14)
O1W—H1W1⋯N1ⁱⁱ	0.83	2.09	2.9178 (14)	173
C10—H10A⋯O1Wⁱⁱⁱ	0.93	2.52	3.3513 (16)	149
C18—H18B⋯O1Wⁱⁱⁱ	0.97	2.59	3.4776 (14)	153

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a Research Fellowship.

supplementary crystallographic information

Comment

Quinolines and their derivatives are important constituents of pharmacologically active synthetic compounds as these systems have been associated with a wide spectrum of biological properties (El-Subbagh et al., 2000) such as DNA binding capability (Atwell et al., 1989) and antitumor activities (Kuo et al., 1993; Xia et al., 1998). The study of Schiff base hydrazones has been growing because of their antimicrobial, anti-tuberculosis and anti-tumour activities (Colins & Lyne, 1970; Ochiai, 1977).

The asymmetric unit of the title compound, (Fig. 1), consists of one 4-chlorobenzaldehyde(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl) hydrazone molecule and one water molecule. One of the H atoms attached to the water molecule is disordered over two positions with the site occupancy ratio of 0.80 (4):0.20 (4). The 1H-imidazo[4,5-c]quinoline ring (C1–C6/N1/C7/C8/N3/C10/N2/C9) is approximately planar with a maximum deviation of 0.0795 (7) Å at atom C2 and it forms a dihedral angle of 7.65 (3)° with the chlorophenyl ring (Cl1/C11–C16) with maximum deviation of 0.0286 (3) Å at atom Cl1. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Loh et al., 2011a,b).

In the crystal packing (Fig. 2), the molecules are linked into chains along the a axis by the water molecules via intermolecular N4—H1N4···O1W, O1W—H1W1···N1, C10—H10A···O1W and C18—H18B···O1W hydrogen bonds (Table 1).

Experimental

A mixture of 4-hydrazino-1-isobutyl-1H-imidazo[4,5-c]quinoline (2.5 g, 0.0098 mole) and 4-chlorobenzaldehyde (1.38 g, 0.0098 mole) in absolute ethanol was refluxed for 4 h in the presence of acetic acid (1 ml). The product, 4-chlorobenzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone, was obtained after cooling and it was crystallized from absolute ethanol. Yield: 3.4 g (80%). Crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation.