1-[(Diethyl­amino­carbon­yl)meth­yl]-2-[hydr­oxy(6-methoxy­quinolin-4-yl)meth­yl]-5-vinyl-1-azoniabicyclo­[2.2.2]octane chloride monohydrate

Li-Ping Zhang; Lin-Juan Wei; Ming-Qing Chen

doi:10.1107/S1600536807068444

. 2008 Jan 25;64(Pt 2):o518. doi: 10.1107/S1600536807068444

1-[(Diethylaminocarbonyl)methyl]-2-[hydroxy(6-methoxyquinolin-4-yl)methyl]-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride monohydrate

Li-Ping Zhang ^a,^*, Lin-Juan Wei ^a, Ming-Qing Chen ^a

PMCID: PMC2960160 PMID: 21201537

Abstract

In the title compound, C₂₆H₃₆N₃O₃ ⁺·Cl⁻·H₂O, the molecular structure of the cation is stabilized by a number of C—H⋯O intramolecular interactions. In the crystal structure, O—H⋯Cl and C—H⋯Cl hydrogen bonds link the ions into a ribbon-like structure along the a axis.

Related literature

For related structures, see: Oleksyn et al. (1979 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

C₂₆H₃₆N₃O₃ ⁺·Cl⁻·H₂O
M _r = 492.04
Orthorhombic,
a = 8.2213 (12) Å
b = 17.441 (3) Å
c = 18.161 (3) Å
V = 2604.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 292 K
0.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.938, T _max = 0.973
15334 measured reflections
5361 independent reflections
3043 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.111
S = 0.99
5361 reflections
311 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ▶), with 2317 Friedel pairs
Flack parameter: 0.14 (9)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 1999 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068444/ci2541sup1.cif

e-64-0o518-sup1.cif^{(25.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068444/ci2541Isup2.hkl

e-64-0o518-Isup2.hkl^{(262.5KB, 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
O2—H2⋯Cl1	0.82	2.25	3.038 (2)	161
C19—H19A⋯Cl1ⁱ	0.97	2.70	3.580 (4)	150
C20—H20B⋯O2	0.97	2.33	3.001 (4)	126
C21—H21B⋯Cl1	0.97	2.76	3.650 (3)	152
C21—H21B⋯O2	0.97	2.58	3.169 (4)	119
O4⋯Cl1ⁱⁱ			3.141 (4)
O4⋯Cl1ⁱⁱⁱ			3.214 (4)

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

Acknowledgments

The authors acknowledge financial support from the Youth Foundation of Jiangnan University (grant No. 104000-52210691).

supplementary crystallographic information

Comment

In the title compound (Fig. 1), the quinoline ring system is planar with a maximum deviation of 0.026 (3) Å for atom C8. Bond lengths and angles are comparable to those observed in a related cinchonine structure (Oleksyn et al., 1979) but the molecules differ slightly in the relative orientations of azoniabicyclo[2.2.2]octane and quinoline units.

The structure of cation is stabilized by a number of C—H···O intramolecular interactions. In the crystal structure O—H···Cl, C—H···Cl and O_w···Cl interactions link the ions into a ribbon along the a axis (Fig.2). Similar packing arrangement is found in the structure of a related cinchonine quaternary salt (Zhang et al., 2006).

Experimental

The title compound was prepared by the reaction of 2-chloro-N,N-diethylacetamide (3 mmol) with quinine (2 mmol) in acetone (5 ml) refluxed for 5 h under a N₂ atmosphere. The resulting precipitate was isolated by filtration, washed, dried, and recrystallized from Et₂O and CH₂Cl₂ (7:1). Single crystals suitable for X-ray diffraction study were obtained from CH₂Cl₂ by slow evaporation at room temperature.