Cocrystal design gone awry? A new dimorphic hydrate of oxalic acid

Mazal Wenger; Joel Bernstein

doi:10.1021/mp070006w

Cocrystal design gone awry? A new dimorphic hydrate of oxalic acid

Mazal Wenger
, Joel Bernstein

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

Abstract

The crystal chemistry of oxalic acid has been studied since 1880, including 37 published structure determinations of the two anhydrous forms (α, β) and the dihydrate, the latest in 2000. In attempts to cocrystallize asparagine or glutamine with oxalic acid, utilizing the particular hydrogen bond synthon R₄²(8), we unexpectedly obtained two previously unreported sesquihydrates of oxalic acid. Form 1 is orthorhombic, Pnma, and the unit cell is a = 11.231(2) Å, b = 12.330(2) Å, c = 6.908(1) Å. Form 2 crystallizes in the triclinic crystal system in space group P1, and the unit cell is a = 6.337(2) Å; b = 7.247(3) Å, c = 10.571 (4)Å, α = 94.34(1)°, β = 100.244(9)°, γ = 97.67(1)°. Both of the new hydrate forms of oxalic acid utilized the R⁴ ²(8) hydrogen bonded synthon.

Original language	English
Pages (from-to)	355-359
Number of pages	5
Journal	Molecular Pharmaceutics
Volume	4
Issue number	3
DOIs	https://doi.org/10.1021/mp070006w
State	Published - 1 May 2007

Keywords

Cocrystals
Hydrates
Polymorphs

ASJC Scopus subject areas

Molecular Medicine
Pharmaceutical Science
Drug Discovery

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10.1021/mp070006w

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@article{75fdaa8142874865a6e9d580581940d3,

title = "Cocrystal design gone awry? A new dimorphic hydrate of oxalic acid",

abstract = "The crystal chemistry of oxalic acid has been studied since 1880, including 37 published structure determinations of the two anhydrous forms (α, β) and the dihydrate, the latest in 2000. In attempts to cocrystallize asparagine or glutamine with oxalic acid, utilizing the particular hydrogen bond synthon R42(8), we unexpectedly obtained two previously unreported sesquihydrates of oxalic acid. Form 1 is orthorhombic, Pnma, and the unit cell is a = 11.231(2) {\AA}, b = 12.330(2) {\AA}, c = 6.908(1) {\AA}. Form 2 crystallizes in the triclinic crystal system in space group P1, and the unit cell is a = 6.337(2) {\AA}; b = 7.247(3) {\AA}, c = 10.571 (4){\AA}, α = 94.34(1)°, β = 100.244(9)°, γ = 97.67(1)°. Both of the new hydrate forms of oxalic acid utilized the R4 2(8) hydrogen bonded synthon.",

keywords = "Cocrystals, Hydrates, Polymorphs",

author = "Mazal Wenger and Joel Bernstein",

year = "2007",

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doi = "10.1021/mp070006w",

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journal = "Molecular Pharmaceutics",

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publisher = "American Chemical Society",

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T1 - Cocrystal design gone awry? A new dimorphic hydrate of oxalic acid

AU - Wenger, Mazal

AU - Bernstein, Joel

PY - 2007/5/1

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N2 - The crystal chemistry of oxalic acid has been studied since 1880, including 37 published structure determinations of the two anhydrous forms (α, β) and the dihydrate, the latest in 2000. In attempts to cocrystallize asparagine or glutamine with oxalic acid, utilizing the particular hydrogen bond synthon R42(8), we unexpectedly obtained two previously unreported sesquihydrates of oxalic acid. Form 1 is orthorhombic, Pnma, and the unit cell is a = 11.231(2) Å, b = 12.330(2) Å, c = 6.908(1) Å. Form 2 crystallizes in the triclinic crystal system in space group P1, and the unit cell is a = 6.337(2) Å; b = 7.247(3) Å, c = 10.571 (4)Å, α = 94.34(1)°, β = 100.244(9)°, γ = 97.67(1)°. Both of the new hydrate forms of oxalic acid utilized the R4 2(8) hydrogen bonded synthon.

AB - The crystal chemistry of oxalic acid has been studied since 1880, including 37 published structure determinations of the two anhydrous forms (α, β) and the dihydrate, the latest in 2000. In attempts to cocrystallize asparagine or glutamine with oxalic acid, utilizing the particular hydrogen bond synthon R42(8), we unexpectedly obtained two previously unreported sesquihydrates of oxalic acid. Form 1 is orthorhombic, Pnma, and the unit cell is a = 11.231(2) Å, b = 12.330(2) Å, c = 6.908(1) Å. Form 2 crystallizes in the triclinic crystal system in space group P1, and the unit cell is a = 6.337(2) Å; b = 7.247(3) Å, c = 10.571 (4)Å, α = 94.34(1)°, β = 100.244(9)°, γ = 97.67(1)°. Both of the new hydrate forms of oxalic acid utilized the R4 2(8) hydrogen bonded synthon.

KW - Cocrystals

KW - Hydrates

KW - Polymorphs

UR - https://www.scopus.com/pages/publications/34250829029

U2 - 10.1021/mp070006w

DO - 10.1021/mp070006w

M3 - Article

C2 - 17500563

AN - SCOPUS:34250829029

SN - 1543-8384

VL - 4

SP - 355

EP - 359

JO - Molecular Pharmaceutics

JF - Molecular Pharmaceutics

IS - 3

ER -

Cocrystal design gone awry? A new dimorphic hydrate of oxalic acid

Abstract

Keywords

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