(E)-N′-(4-Pyridylmethyl­ene)-4-(8-quinol­yl­oxy)butanohydrazide 0.25-hydrate

Min-E Chen; Jia-Ming Li

doi:10.1107/S160053680900110X

. 2009 Jan 14;65(Pt 2):o295. doi: 10.1107/S160053680900110X

(E)-N′-(4-Pyridylmethylene)-4-(8-quinolyloxy)butanohydrazide 0.25-hydrate

Min-E Chen ^a, Jia-Ming Li ^a,^*

PMCID: PMC2968356 PMID: 21581905

Abstract

The asymmetric unit of the title compound, C₁₉H₁₈N₄O₂·0.25H₂O, contains two organic molecules and a solvent water molecule with 50% occupancy. The two molecules differ in their conformations: in one molecule it is (+)gauche-trans-trans-(+)gauche-trans, whereas in the other it is (−)gauche-trans-trans-(−)gauche-trans. The dihedral angles between the pyridine ring and the quinoline ring system are 67.4 (3) and 68.0 (2)°. Molecules are linked into a supramolecular two-dimensional array via N—H⋯N hydrogen bonds, with each partially occupied water molecule connected via an O—H⋯O hydrogen bond. C—H⋯O interactions are also present.

Related literature

For general background, see: Cai et al. (2003 ▶); Chen et al. (2005 ▶); Park et al. (2006 ▶); Karmakar et al. (2007 ▶). For related structures, see: Zheng et al. (2006 ▶, 2007 ▶, 2008 ▶); Xie et al. (2008 ▶).

Experimental

Crystal data

C₁₉H₁₈N₄O₂·0.25H₂O
M _r = 1355.51
Monoclinic,
a = 8.8816 (13) Å
b = 17.420 (2) Å
c = 11.3624 (17) Å
β = 100.765 (3)°
V = 1727.0 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.32 × 0.26 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.972, T _max = 0.981
9142 measured reflections
3169 independent reflections
1927 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.162
S = 1.01
3169 reflections
460 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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/S160053680900110X/tk2355sup1.cif

e-65-0o295-sup1.cif^{(28.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900110X/tk2355Isup2.hkl

e-65-0o295-Isup2.hkl^{(155.5KB, 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
C22—H22⋯O4ⁱ	0.93	2.51	3.224 (7)	134
C7—H7⋯N8ⁱⁱ	0.93	2.55	3.466 (9)	167
C3—H3⋯O2ⁱⁱⁱ	0.93	2.52	3.353 (7)	150
C2—H1⋯N4^iv	0.93	2.55	3.390 (9)	150
O5—H39⋯O4^v	0.85	2.17	2.964 (10)	156
N6—H6⋯N1ⁱⁱⁱ	0.86	2.10	2.934 (6)	163
N2—H2⋯N5ⁱ	0.86	2.25	3.077 (7)	161

Open in a new tab

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

Acknowledgments

This work was supported by grants from Qinzhou University Foundation and the Young Key Teacher’s Plan of Guangxi Zhuang Autonomous Region of the People’s Republic of China [grant Nos. 2008XJKY-10B and 2008(30)].

supplementary crystallographic information

Comment

The coordination chemistry of 8-hydroxyquinoline and its derivatives is well studied (Cai et al., 2003; Chen et al., 2005; Park et al., 2006; Karmakar et al. 2007). In the course of our studies searching for good extractants of metal ions, the title compound, (I), was synthesized and its crystal structure determined. The asymmetric unit comprises two independent molecules which differ in conformation and a water molecule with a 50% site occupancy factor. In one molecule, the conformation along the O1—C10—C11—C12—C13—N2—N3—C14 bond sequence is (+)gauche-trans-trans-(+)gauche-trans, whereas in the second molecule the conformation is (-)gauche-trans-trans-(-)gauche-trans along the corresponding O3—C29—C30—C31—C32—N6—N7—C33 bond sequence. Despite these differences, the dihedral angles between the mean planes of the pyridine and quinoline rings are not very different, i.e. 67.4 (3)° and 68.0 (2)° for the molecules containing atoms O1 and O3, respectively. The two independent molecules are linked to a supermolecular 2D array via N—H···N hydrogen bonds supported by C—H···O contacts, Table 1. Each partially occupied water molecules is connected to a layer via a O—H···O hydrogen bond.

Experimental

4-(Quinolin-8-yloxy)butanohydrazide (0.01 mol), 4-pyridylaldehyde (0.01 mol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask, and refluxed for 8 h. After cooling to room temperature, the mixture was filtered. Colourless crystals were obtained by slow evaporation of a tetrahydrofuran solution over a period of 2 days; m.p. 438 K. Analysis found: C 67.34, H 5.50, N 16.53; C₇₆H₇₄N₁₆O₉ requires: C 67.30, H 5.54, N 16.51.