(E)-N′-(5-Chloro-2-hydroxy­benzyl­idene)-4-(8-quinol­yloxy)butanohydrazide monohydrate

Jian Zhang; Guo-Lun XiaHou; Sheng-Sen Zhang; Jing Zeng

doi:10.1107/S1600536809023733

. 2009 Jun 27;65(Pt 7):o1695–o1696. doi: 10.1107/S1600536809023733

(E)-N′-(5-Chloro-2-hydroxybenzylidene)-4-(8-quinolyloxy)butanohydrazide monohydrate

Jian Zhang ^a, Guo-Lun XiaHou ^a, Sheng-Sen Zhang ^a, Jing Zeng ^a,^*

PMCID: PMC2969487 PMID: 21582950

Abstract

The crystal of the title Schiff base compound, C₂₀H₁₈ClN₃O₃·H₂O, was twinned by a twofold rotation about (100). The asymmetric unit contains two crystallographically independent molecules with similar conformations, and two water molecules. The C=N—N angles of 115.7 (6) and 116.2 (6)° are significantly smaller than the ideal value of 120° expected for sp ²-hybridized N atoms and the dihedral angles between the benzene ring and quinoline ring system in the two molecules are 52.5 (7) and 53.9 (7)°. The molecules aggregate via C—Cl⋯π and π–π interactions [centroid–centroid distances = 3.696 (5)–3.892 (5) Å] and weak C—H⋯O interactions as parallel sheets, which are further linked by water molecules through N—H⋯O and O—H⋯O hydrogen bonds into a supramolecular two-dimensional network.

Related literature

For background to the rational construction of new matallosupramolecular architectures, see: Muraoka et al. (1998 ▶); Cai et al. (2003 ▶); Pallavicini et al. (2007 ▶). For the use of 8-hydroxyquinoline and its derivatives as ligands in this area, see: Chen et al. (2005 ▶); Park et al. (2006 ▶); Karmakar et al. (2007 ▶). For related structures, see: Xu et al. (2002 ▶); Zhang et al. (2005 ▶); Wen et al. (2005 ▶); Wei et al. (2004 ▶); Zheng, Li et al. (2008 ▶); Zheng, Wu, Lu et al., (2006 ▶); Zheng (2006 ▶); Zheng, Qiu et al. (2006 ▶); Zheng, Wu, Li et al. (2007 ▶); Xie et al. (2008 ▶); Chen & Li (2009 ▶). For comparative bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₀H₁₈ClN₃O₃·H₂O
M _r = 401.84
Monoclinic,
a = 11.167 (3) Å
b = 11.150 (3) Å
c = 30.909 (10) Å
β = 96.970 (12)°
V = 3820 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 K
0.32 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.929, T _max = 0.977
17043 measured reflections
5912 independent reflections
3796 reflections with I > 2σ(I)
R _int = 0.093

Refinement

R[F ² > 2σ(F ²)] = 0.079
wR(F ²) = 0.198
S = 1.02
5912 reflections
508 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983), 2525 Friedel pairs
Flack parameter: 0.08 (13)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023733/pk2173sup1.cif

e-65-o1695-sup1.cif^{(30.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023733/pk2173Isup2.hkl

e-65-o1695-Isup2.hkl^{(289.4KB, 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—H2⋯O7ⁱ	0.86	2.07	2.836 (9)	147
N5—H5⋯O8ⁱⁱ	0.86	2.05	2.820 (9)	149
O3—H3⋯N3	0.82	1.92	2.630 (8)	144
O6—H6⋯N6	0.82	1.91	2.633 (9)	147
O7—H29⋯N1	0.85	2.05	2.876 (8)	165
O7—H30⋯O5ⁱⁱⁱ	0.85	2.06	2.839 (9)	153
O8—H31⋯N4	0.85	2.04	2.872 (9)	166
O8—H32⋯O2^iv	0.85	1.99	2.845 (9)	180
C7—H7⋯O6ⁱⁱⁱ	0.93	2.53	3.267 (10)	137
C27—H27⋯O3^v	0.93	2.56	3.303 (10)	137
C19—Cl1⋯Cg5^vi	1.74 (1)	3.63 (1)	4.127 (9)	94 (1)
C39—Cl2⋯Cg1^vii	1.76 (1)	3.62 (1)	4.109 (9)	93 (1)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) . Cg1 and Cg2 are the centroids of the N1/C8/C7/C6/C5/C9 and N4/C28/C27/C26/C25/C29 rings, respectively.

Acknowledgments

This work was supported by the Key Laboratory for Research and Development of Natural Drugs of Jiangxi Province.

supplementary crystallographic information

Comment

The rational construction of new matallosupramolecular architectures using logical combinations of rigid linear and angular components, has been the subject of much study during the last decade (Muraoka et al.,1998; Cai et al., 2003; Pallavicini et al., 2007). Most commonly, nitrogen heterocycles have been used to provide donors for coordination to metals within these assemblies, with pyridine rings being by far the most frequently used. More recently, flexible ligands have been employed to obtain access to topologies that are not available using more rigid ligands. Such flexibility can be introduced by means of combinations of methylene, ether, or thioether spacer groups between the donor sites, which permit the ligand to exist in various combinations as a result of rotations about single bonds. 8-Hydroxyquinoline and its derivatives are among the most extensively investigated ligands in this area (Xu et al., 2002; Cai et al., 2003; Chen et al., 2005; Park et al., 2006; Karmakar et al., 2007; Zhang et al., 2005; Wen et al., 2005, Wei et al., 2004; Zheng, Li et al., 2008). In this contribution, we present the synthesis and crystal structure of a new ligand, which contains oxygen and nitrogen donors and flexible aliphatic spacers.

The bond lengths and angles are in good agreement with expected values (Allen et al., 1987) and are comparable to those in the related compounds (Zheng, Wu, Lu et al., 2006; Zheng, 2006; Zheng, Wu, Li et al., 2007; Xie et al., 2008; Chen & Li, 2009). X-ray crystallography reveals that the title compound was twinned by a 2-fold rotation about (100). The crystals contain two crystallographically independent molecules with similar conformations, and two water molecules. The conformation along the C1—O1—C10—C11—C12—C13—N2—N3—C14—C15 and C21—O4—C30—C31—C32—C33—N5—N6—C34—C35 bond sequence are all trans (Fig.1). The C14—N3 and C34—N6 bond lengths of 1.290 (9) and 1.283 (9) Å respectively, indicate the presence of a typical C=N. The CN—N angle of 115.7 (6) and 116.2 (6)° are significantly smaller than the ideal value of 120° expected for sp²-hybridized N atoms and the dihedral angles between the benzene ring and quinoline ring system in the two molecules are 52.5 (7) and 53.9 (7)°. This is probably a consequence of repulsion between the nitrogen lone pairs and the adjacent N atom (Zheng, Qiu et al., 2006). All torsion angles involving non-H atoms are close to 180°, which indicates that the molecules are essentially planar with the C=N bond adjacent to the benzene ring and quinoline group adopting a trans configuration with respect to its substitution. In the crystal packing, intramolecular O—H···N hydrogen bonds produce S(6) ring motifs (Bernstein et al.,1995) and there are also significant π-stacking interactions between the planar sections associated with the benzene ring and quinoline group. The organic molecules aggregate via intermolecular weak C—Cl···π and π–π interactions between the benzene ring and quinoline rings [centroid-centroid distances in the range of 3.696 (5)–3.892 (5) Å] and weak C—H···O contacts into an array of parallel sheets, and these layers are further linked by water molecules via N—H···O and O—H···O hydrogen bonds into a supramolecular two dimensional network (Fig. 2 and Table 1).

Experimental

Reagents and solvents were of commercially available quality. The title complex was synthesized according to the method of Zheng, Li et al. 2008. 2-(quinolin-8-yloxy)butanehydrazide (0.01 mol), 5-chloro-2-hydroxybenzaldehyde (0.01 mol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask and refluxed for 6 h. After cooling to room temperature, the solid product was separated by filtration. Yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation of a tetrahydrofuran solution over a period of 2 d.