Bis[N-benzyl-2-(quinolin-8-yl­oxy)acetamide] monohydrate

Ming-Shi Wang; Hai-Yan Li; Wei-Na Wu

doi:10.1107/S1600536811019817

. 2011 Jun 4;67(Pt 7):o1558. doi: 10.1107/S1600536811019817

Bis[N-benzyl-2-(quinolin-8-yloxy)acetamide] monohydrate

Ming-Shi Wang ^a, Hai-Yan Li ^b, Wei-Na Wu ^b,^*

PMCID: PMC3152141 PMID: 21836972

Abstract

In the title compound, 2C₁₈H₁₆N₂O₂·H₂O, the dihedral angles between the quinoline rings and the benzene rings in the two independent acetamide molecules are 80.09 (5) and 61.23 (5)°. The crystal packing is stablized by O—H⋯N and N—H⋯O hydrogen bonds between the acetamide and water molecules.

Related literature

For the luminescent properties of lanthanide complexes with amide-type ligands, see: Li et al. (2003 ▶); Wu et al. (2006 ▶). For the synthesis of 2-chloro-N-benzylacetamide and N-benzyl-2-(quinolin-8-yloxy)acetamide, see: Wu et al. (2006 ▶). For the structure of a copper(II) complex with N-benzyl-2-(quinolin-8-yloxy)acetamide, see: Wang et al. (2010 ▶).

Experimental

Crystal data

2C₁₈H₁₆N₂O₂·H₂O
M _r = 602.67
Monoclinic,
a = 13.7802 (12) Å
b = 12.3129 (11) Å
c = 18.9865 (17) Å
β = 101.066 (2)°
V = 3161.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.21 × 0.16 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.984, T _max = 0.987
16274 measured reflections
5562 independent reflections
3572 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.092
S = 1.10
5562 reflections
413 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: APEX2 (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 datablock(s) I, global. DOI: 10.1107/S1600536811019817/vm2098sup1.cif

e-67-o1558-sup1.cif^{(27.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019817/vm2098Isup2.hkl

e-67-o1558-Isup2.hkl^{(272.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811019817/vm2098Isup3.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—H2A⋯O5ⁱ	0.86	2.09	2.903 (2)	157
N4—H4A⋯O5	0.86	2.10	2.9015 (19)	154
O5—H5B⋯N1ⁱⁱ	0.88 (1)	2.01 (2)	2.869 (2)	167 (2)
O5—H5C⋯N3	0.88 (1)	1.91 (2)	2.7849 (19)	173 (2)

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

Acknowledgments

The authors are grateful for financial support from the Doctoral Foundation of Henan Polytechnic University (B2009–70 648359).

supplementary crystallographic information

Comment

The amide type open-chain ligands have attracted much attention mainly because of their excellent coordination ability and high selectivity to metal ions (Li et al., 2003 & Wu et al., 2006). Previously, we have reported the structure of the copper(II) complex with the title acetamide molecular (Wang et al., 2010). In this paper, the title compound was synthesized and characterized by X-ray diffraction.

In the title compound, 2C₁₈H₁₆N₂O₂.H₂O, there are two independent N-benzyl-2-(quinolin-8-yloxy)acetamide molecules and a water molecule in the asymmetric unit (Fig. 1). Bond lengths and angles of the acetamide molecular are comparable with those observed in its copper(II) complex (Wang et al., 2010). The dihedral angles between the quinoline rings (N1/C1–C9, r.m.s. deviation 0.0092Å and N3/C19–C27, r.m.s. deviation 0.0293 Å) and the benzene rings (C13–C18, r.m.s. deviation 0.0028Å and C31–C35, r.m.s. deviation 0.0039 Å) in two independent acetamide molecules are 80.09 (5)° and 61.23 (5)°, respectively. In the crystal structure, solvent water molecules form intermolecular O—H···N and N—H···O hydrogen bonds with acetamide molecules to stabilize the packing (Table 1, Fig. 2).

Experimental

8-Hydroxyquinoline (1.5 g, 10.3 mmol) and anhydrous potassium carbonate (1.6 g, 11.6 mmol) were added to DMF (15 mL), then 2-chloro-N-benzylacetamide (1.83 g, 10.0 mmol) and a small quantity of KI were added. The reaction mixture was stirred for 5 h at 100–110 °C. After cooling down, 150 mL water was added and stirred for 2 h. The precipitate was collected by filtration and washed with water. Recrystallization from EtOH/H₂O (1:1) gave colorless blocks.