Interpreting the disordered crystal structure of Sodium Naproxen Tetrahydrate

Andrew Bond; Claus Cornett; Flemming Hofmann Larsen; Haiyan Qu; Dharaben Kaushikkumar Raijada; Jukka Rantanen

doi:10.1021/cg400688c

Interpreting the disordered crystal structure of Sodium Naproxen Tetrahydrate

Andrew Bond, Claus Cornett, Flemming Hofmann Larsen, Haiyan Qu, Dharaben Kaushikkumar Raijada, Jukka Rantanen

Food Analytics and Biotechnology

9 Citationer (Scopus)

Abstract

The crystal structure of the tetrahydrate of the active pharmaceutical ingredient sodium naproxen is examined using single-crystal X-ray diffraction, supported by ¹³C and ²³Na solid-state NMR. The structure has previously been reported to be a heminonahydrate, Na ⁺(naproxen^-)·4.5H₂O. The average structure in space group C2 contains layers of naproxen molecules that are ordered, except for two orientations of the carboxyl groups, and Na ⁺/H₂O regions that exhibit complex disorder. The atomic positions in the disordered regions are interpreted as Na(H₂O) ₆ octahedra, alternately sharing edges and faces to define 1-D coordination polymers with translational periodicity twice that of the b axis in the average C2 structure. There is also one noncoordinated H₂O molecule per two naproxen molecules, giving an overall formula of {Na ₂(H₂O)₇}²⁺(naproxen ^-)₂(H₂O). Two resonances seen for the naproxen methyl group in ¹³C CP/MAS SS-NMR are accounted for by the presence of two orientations along the doubled b axis for the carboxyl group. A single resonance in the ²³Na SS-NMR is consistent with local 2₁/m symmetry in the Na⁺/H₂O regions. The single-crystal X-ray diffraction pattern contains diffuse rods in positions consistent with the doubled b axis, indicating a disordered stacking sequence for the Na ⁺/H₂O sections.

Originalsprog	Engelsk
Tidsskrift	Crystal Growth & Design
Vol/bind	13
Udgave nummer	8
Sider (fra-til)	3665−3671
Antal sider	7
ISSN	1528-7483
DOI	https://doi.org/10.1021/cg400688c
Status	Udgivet - 7 aug. 2013

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10.1021/cg400688c

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title = "Interpreting the disordered crystal structure of Sodium Naproxen Tetrahydrate",

abstract = "The crystal structure of the tetrahydrate of the active pharmaceutical ingredient sodium naproxen is examined using single-crystal X-ray diffraction, supported by 13C and 23Na solid-state NMR. The structure has previously been reported to be a heminonahydrate, Na +(naproxen-)·4.5H2O. The average structure in space group C2 contains layers of naproxen molecules that are ordered, except for two orientations of the carboxyl groups, and Na +/H2O regions that exhibit complex disorder. The atomic positions in the disordered regions are interpreted as Na(H2O) 6 octahedra, alternately sharing edges and faces to define 1-D coordination polymers with translational periodicity twice that of the b axis in the average C2 structure. There is also one noncoordinated H2O molecule per two naproxen molecules, giving an overall formula of {Na 2(H2O)7}2+(naproxen -)2(H2O). Two resonances seen for the naproxen methyl group in 13C CP/MAS SS-NMR are accounted for by the presence of two orientations along the doubled b axis for the carboxyl group. A single resonance in the 23Na SS-NMR is consistent with local 21/m symmetry in the Na+/H2O regions. The single-crystal X-ray diffraction pattern contains diffuse rods in positions consistent with the doubled b axis, indicating a disordered stacking sequence for the Na +/H2O sections.",

author = "Andrew Bond and Claus Cornett and Larsen, {Flemming Hofmann} and Haiyan Qu and Raijada, {Dharaben Kaushikkumar} and Jukka Rantanen",

year = "2013",

month = aug,

day = "7",

doi = "10.1021/cg400688c",

language = "English",

volume = "13",

pages = "3665−3671",

journal = "Crystal Growth & Design",

issn = "1528-7483",

publisher = "American Chemical Society",

number = "8",

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TY - JOUR

T1 - Interpreting the disordered crystal structure of Sodium Naproxen Tetrahydrate

AU - Bond, Andrew

AU - Cornett, Claus

AU - Larsen, Flemming Hofmann

AU - Qu, Haiyan

AU - Raijada, Dharaben Kaushikkumar

AU - Rantanen, Jukka

PY - 2013/8/7

Y1 - 2013/8/7

N2 - The crystal structure of the tetrahydrate of the active pharmaceutical ingredient sodium naproxen is examined using single-crystal X-ray diffraction, supported by 13C and 23Na solid-state NMR. The structure has previously been reported to be a heminonahydrate, Na +(naproxen-)·4.5H2O. The average structure in space group C2 contains layers of naproxen molecules that are ordered, except for two orientations of the carboxyl groups, and Na +/H2O regions that exhibit complex disorder. The atomic positions in the disordered regions are interpreted as Na(H2O) 6 octahedra, alternately sharing edges and faces to define 1-D coordination polymers with translational periodicity twice that of the b axis in the average C2 structure. There is also one noncoordinated H2O molecule per two naproxen molecules, giving an overall formula of {Na 2(H2O)7}2+(naproxen -)2(H2O). Two resonances seen for the naproxen methyl group in 13C CP/MAS SS-NMR are accounted for by the presence of two orientations along the doubled b axis for the carboxyl group. A single resonance in the 23Na SS-NMR is consistent with local 21/m symmetry in the Na+/H2O regions. The single-crystal X-ray diffraction pattern contains diffuse rods in positions consistent with the doubled b axis, indicating a disordered stacking sequence for the Na +/H2O sections.

AB - The crystal structure of the tetrahydrate of the active pharmaceutical ingredient sodium naproxen is examined using single-crystal X-ray diffraction, supported by 13C and 23Na solid-state NMR. The structure has previously been reported to be a heminonahydrate, Na +(naproxen-)·4.5H2O. The average structure in space group C2 contains layers of naproxen molecules that are ordered, except for two orientations of the carboxyl groups, and Na +/H2O regions that exhibit complex disorder. The atomic positions in the disordered regions are interpreted as Na(H2O) 6 octahedra, alternately sharing edges and faces to define 1-D coordination polymers with translational periodicity twice that of the b axis in the average C2 structure. There is also one noncoordinated H2O molecule per two naproxen molecules, giving an overall formula of {Na 2(H2O)7}2+(naproxen -)2(H2O). Two resonances seen for the naproxen methyl group in 13C CP/MAS SS-NMR are accounted for by the presence of two orientations along the doubled b axis for the carboxyl group. A single resonance in the 23Na SS-NMR is consistent with local 21/m symmetry in the Na+/H2O regions. The single-crystal X-ray diffraction pattern contains diffuse rods in positions consistent with the doubled b axis, indicating a disordered stacking sequence for the Na +/H2O sections.

U2 - 10.1021/cg400688c

DO - 10.1021/cg400688c

M3 - Journal article

SN - 1528-7483

VL - 13

SP - 3665−3671

JO - Crystal Growth & Design

JF - Crystal Growth & Design

IS - 8

ER -

Interpreting the disordered crystal structure of Sodium Naproxen Tetrahydrate

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