2-(3-Morpholino­prop­yl)-2,3-dihydro-1H-pyrrolo­[3,4-b]quinolin-1-one monohydrate

Yu-Hua Long; Ting Zhou; Ding-Qiao Yang; Wen-Ling Wang; Han-Mei Zhang

doi:10.1107/S1600536810046349

. 2010 Nov 13;66(Pt 12):o3180. doi: 10.1107/S1600536810046349

2-(3-Morpholinopropyl)-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one monohydrate

Yu-Hua Long ^a,^*, Ting Zhou ^a, Ding-Qiao Yang ^a, Wen-Ling Wang ^a, Han-Mei Zhang ^a

PMCID: PMC3011724 PMID: 21589475

Abstract

In the title compound, C₁₈H₂₁N₃O₂·H₂O, the fused-ring system is approximately planar [maximum atomic deviation = 0.028 (3) Å]; the morpholine ring displays a chair conformation. The crystal packing is stabilized by classical intermolecular O—H⋯O and O—H⋯N hydrogen bonds and weak C—H⋯O hydrogen bonds between the organic molecules and the water molecules.

Related literature

For the properties and biological activity of quinoline derivatives, see: Vaitilingam et al. (2004 ▶); Lee et al. (2004 ▶); Zwaagstra et al. (1998 ▶); Roma et al. (2000 ▶); Ferrarini et al. (2000 ▶). For the preparation of quinoline derivatives, see: Zhou et al. (2010 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

C₁₈H₂₁N₃O₂·H₂O
M _r = 329.39
Orthorhombic,
a = 7.0107 (16) Å
b = 12.655 (3) Å
c = 37.609 (9) Å
V = 3336.7 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
15458 measured reflections
2943 independent reflections
1864 reflections with I > 2σ(I)
R _int = 0.067

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.144
S = 1.04
2943 reflections
225 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 global, I. DOI: 10.1107/S1600536810046349/xu5085sup1.cif

e-66-o3180-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046349/xu5085Isup2.hkl

e-66-o3180-Isup2.hkl^{(144.5KB, 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
O1W—H1W⋯N3ⁱ	0.86 (4)	2.15 (4)	2.961 (4)	155 (4)
O1W—H2W⋯O1ⁱⁱ	0.87 (4)	1.98 (4)	2.843 (3)	174 (4)
C11—H11B⋯O1W	0.97	2.47	3.326 (4)	147

Open in a new tab

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

Acknowledgments

We are grateful to the National Natural Science Foundation of China (grant No. 20802021) and the Natural Science Foundation of Guangdong Province, China (grant No. 8251063101000002).

supplementary crystallographic information

Comment

Quinoline analogues have been reported to display promising antibacterial (Vaitilingam et al., 2004), an-ticancer and antiplatelet (Lee et al., 2004), antiasthmatic (Zwaagstra et al., 1998), antiinflammatory (Roma et al., 2000), and antihypertensive activities (Ferrarini et al., 2000). We have synthesized some new quinoline derivatives (Yang et al., 2008). In continuation of our efforts to develop quinoline derivatives with a new structure-activity relationship, herein, we report the synthesis and structure determination the title compound.

The molecular geometry and the atom-labeling scheme of the title compound is illustrated in Fig. 1. The molecule contains three approximately coplanar rings and the dihedral angle between the three rings 1.60 (2)° and 1.20 (5)°, respectively; the C—N2—C—C torsion angles are 43.59° and -137.51°; the morpholine ring shows a stable chair conformation. The crystal structure can be depicted as layers along a-axis which ring systems are parallel to one another. The crystal packing is stabilized by intermolecular interactions between O and H atoms [C—H···O = 2.638Å].

Experimental

The precursor, ethyl 2-(bromomethyl)quinoline-3-carboxylate, was prepared according to the literature procedure (Yang et al., 2008; Zhou et al., 2010). The title compoud was synthesized by treating 1 mmol of ethyl 2-(bromomethyl)quinoline-3-carboxylate with 1.2 mmol of 3-morpholinopropan-1-amine in the presence of NaHCO₃ in acetonitrile. The reaction was carried out under the stirring at room temperature for 10 h. Once the reaction was complete, the solid salt was filtered off and the filtrate was then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the mixture of methanol and ethyl acetate (v /v = 1/20) to afford the white product. Crystals suitable for X-ray analysis were obtained by slow evaporation of the solution of petroleum ether and dichloromethane, in which the small amount of water was not removed.