2-[(5,7-Dibromo­quinolin-8-yl)­oxy]-N-(2-meth­oxy­phen­yl)acetamide

Yong-Hong Wen; Hong-Qing Qin; Hui-Ling Wen

doi:10.1107/S1600536810048312

. 2010 Nov 24;66(Pt 12):o3294. doi: 10.1107/S1600536810048312

2-[(5,7-Dibromoquinolin-8-yl)oxy]-N-(2-methoxyphenyl)acetamide

Yong-Hong Wen ^a,^*, Hong-Qing Qin ^a, Hui-Ling Wen ^a

PMCID: PMC3011411 PMID: 21589573

Abstract

In the title compound, C₁₈H₁₄Br₂N₂O₃, an intramolecular N—H⋯N hydrogen bond forms an eight-membered ring. The dihedral angle between the planes of the quinoline system and the benzene ring is 41.69 (1)°. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds and short Br⋯O interactions [3.0079 (19) Å].

Related literature

The structure of N,N-dicyclohexyl-2-(5,7-dibromoquinolin-8-yloxy)acetamide has been reported by Liu et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For applications of 8-hydroxyquinoline and its derivatives, see: Bratzel et al. (1972 ▶). Some 8-hydroxyquinoline derivatives and their transition metal complexes exhibit antibacterial activity, see: Patel & Patel (1999 ▶).

Experimental

Crystal data

C₁₈H₁₄Br₂N₂O₃
M _r = 466.13
Monoclinic,
a = 8.7570 (18) Å
b = 8.7279 (17) Å
c = 22.372 (5) Å
β = 98.04 (3)°
V = 1693.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 4.81 mm⁻¹
T = 293 K
0.06 × 0.02 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.761, T _max = 0.910
12864 measured reflections
4027 independent reflections
3316 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.093
S = 1.06
4027 reflections
231 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048312/hg2753sup1.cif

e-66-o3294-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048312/hg2753Isup2.hkl

e-66-o3294-Isup2.hkl^{(197.4KB, 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—H2A⋯N1	0.90 (1)	2.24 (1)	3.065 (3)	153 (1)
C18—H18C⋯O2ⁱ	0.96	2.53	3.342 (3)	142

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20971076), the Outstanding Adult–young Scientific Research Encouraging Foundation of Shandong Province, China (No. 2008BS0901). The authors acknowledge X.-F. Tang’s help with this paper.

supplementary crystallographic information

Comment

8-Hydroxyquinoline and its derivatives have found extensive application as analytical reagents, e.g. in absorption spectrophotometry, fluorimetry, solvent extraction and partition chromatography (Bratzel et al., 1972). Some 8-hydroxyquinoline derivatives and their complexes with transition metals demonstrate antibacterial activity (Patel & Patel,1999). Recently, the structure of 5,7-dibromosubstituted 8-hydroxyquinolinate amide-type compound, namely N,N-dicyclohexyl-2-(5,7-dibromoquinolin-8-yloxy)acetamide, (II), has been reported (Liu et al., 2007). Here, we have synthesized and carried out the structure determination of the title compound, (I), (Fig. 1).

All bond lengths in (I) are within normal ranges (Allen et al., 1987) and comparable with those in the related compound (II). The sum of the angles around atoms N2 and C11 are 359.9° and 360.0°, respectively, implying a planar configuration. There is one intramolecular hydrogen bond, viz. N2—H2···N1 (Table 1), forming one larger eight-membered ring. The dihedral angle between the planes of the quinoline system and the benzene ring is 41.69 (1)°. The crystal packing is stabilized by intermolecular C18—H18C···O2 hydrogen bond (Table 1) and Br···O short-contact interactions.

Experimental

To a solution of 5,7-dibromo-8-hydroxyquinoline (3.02 g, 10 mmol) in acetone (60 ml) were added 2-chloro-N-(4-methoxyphenyl)acetamide (2.0 g,10 mmol), K₂CO₃ (1.52 g, 11 mmol) and KI (0.5 g), and the resulting mixture was stirred at 333 K for 5 h. After cooling to room temperature, the mixture was washed three times with water and filtered. Colourless single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an acetone solution over a period of 6 d.