4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-[2-(2-methyl-4-oxo-6,7,8,9-tetra­hydro-4H-pyrido[1,2-a]pyrimidin-3-yl)eth­yl]piperidinium nitrate

Yu Sun; Huai-Hong Zhang

doi:10.1107/S1600536809022016

. 2009 Jun 20;65(Pt 7):o1647. doi: 10.1107/S1600536809022016

4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-[2-(2-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-3-yl)ethyl]piperidinium nitrate

Yu Sun ^a,^b,^*, Huai-Hong Zhang ^a

PMCID: PMC2969342 PMID: 21582911

Abstract

In the risperidone cation of the title compound, C₂₃H₂₈FN₄O₂ ⁺·NO₃ ⁻, the piperidine ring adopts a chair conformation and the tetrahydropyridine ring is disordered over two orientations in a 0.620 (11):0.380 (11) ratio. N—H⋯O, C—H⋯O and C—H⋯F hydrogen bonds are present in the crystal structure.

Related literature

Risperidone is an antipsychotic agent belonging to a new chemical class of benzisoxazole derivatives, see: Callaghan et al. (1999 ▶); Tandon (2002 ▶).

Experimental

Crystal data

C₂₃H₂₈FN₄O₂ ⁺·NO₃ ⁻
M _r = 473.50
Monoclinic,
a = 8.1655 (16) Å
b = 21.866 (4) Å
c = 12.635 (3) Å
β = 91.94 (3)°
V = 2254.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 (2) K
0.15 × 0.12 × 0.09 mm

Data collection

Rigaku Scxmini 1K CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T _min = 0.94, T _max = 0.99
22497 measured reflections
5164 independent reflections
3386 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.176
S = 1.04
5164 reflections
325 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536809022016/xu2503sup1.cif

e-65-o1647-sup1.cif^{(25.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022016/xu2503Isup2.hkl

e-65-o1647-Isup2.hkl^{(247.8KB, 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—H2B⋯O3ⁱ	0.89 (3)	2.07 (3)	2.866 (3)	149 (2)
N2—H2B⋯O5ⁱ	0.89 (3)	2.33 (3)	3.157 (5)	156 (2)
C2—H2A⋯O2ⁱⁱ	0.93	2.19	3.107 (3)	171
C10—H10A⋯O4	0.97	2.50	3.221 (4)	131
C13—H13B⋯Fⁱⁱⁱ	0.97	2.33	3.264 (3)	161

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

supplementary crystallographic information

Comment

Risperidone is an antipsychotic agent belonging to a new chemical class of benzisoxazole derivatives, available worldwide since the early 1990s (Callaghan et al., 1999; Tandon, 2002). We report here the synthesis and crystal structure of the title complex, (I) (Fig. 1).

In the structure of (I), there is one risperidone cation and one NO₃^- anion in the asymmetric unit. The expected proton transfer from nitric acid to risperidone occurs at atom N2 of the piperidine ring. Consequently, atom N2 shows quaternary character and bears a positive charge. Compound (I) contains a piperidine ring, one end of which is connected to a pyridopyrimidine group via an ethyl bridge, while the other end is connected to an almost-planar fluorobenzisoxazole ring system. In the crystal structure of the title compound, an elaborate hydrogen-bond network is formed. Each NO₃^-, one amino group and one carbonyl group in the risperidone molecule are involved in the hydrogen-bond network (Table 1, Fig. 2).

Experimental

All of the reagents and solvents were purchased from either Aldrich and used without further purification. The compound was recrystallized from a solution in a mixture of methanol and water, with the pH adjusted to 5–6 using 0.1 mol/l HNO₃, giving colourless crystals of (I) suitable for X-ray diffraction.