A 1:1 Cocrystal of Caffeine and 2-Hydroxy-1-Naphthoic Acid Obtained via a Slurry Screening Method

Dejan-Krešimir Bučar; Rodger Henry; Richard Duerst; Xiaochun Lou; Leonard MacGillivray; Geoff Zhang

doi:10.1007/s10870-010-9766-y

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A 1:1 Cocrystal of Caffeine and 2-Hydroxy-1-Naphthoic Acid Obtained via a Slurry Screening Method

Journal article

Peer reviewed

A 1:1 Cocrystal of Caffeine and 2-Hydroxy-1-Naphthoic Acid Obtained via a Slurry Screening Method

Dejan-Krešimir Bučar, Rodger Henry, Richard Duerst, Xiaochun Lou, Leonard MacGillivray and Geoff Zhang

Journal of chemical crystallography, Vol.40(11), pp.933-939

11/2010

DOI: 10.1007/s10870-010-9766-y

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Abstract

A cocrystal of caffeine (caf) and 2-hydroxy-1-naphthoic acid (2H1NA), namely, (caf)·(2H1NA), was discovered via a screening method based on solution-mediated phase transformation (SMPT). The components crystallize as a two-component hydrogen-bonded assembly involving both an intermolecular O–H···N and intramolecular O–H···O hydrogen bond. The assemblies stack parallel and offset. Crystal data: monoclinic P 21/n space group, a = 7.909(2) Å, b = 15.275(5) Å, c = 14.704(5) Å, β = 103.66(1)°, Z = 4, V = 1726.1(9) Å3, D c = 1.471 g/cm3 and R 1 = 0.081, wR 2 = 0.163. The cocrystal (caf)·(2H1NA) was also subjected to polymorph screening using 15 different solvents, with all resulting solids being identified as the original form.A cocrystal of caffeine and 2-hydroxy-1-naphthoic acid was discovered via a screening method and is shown to form a two-component hydrogen-bonded molecular assembly based on an intermolecular O–H⋯N and intramolecular O–H⋯O hydrogen bond.

Caffeine

Chemistry

Cocrystal screening

Crystallography

Inorganic Chemistry

Organometallic Chemistry

Pharmaceutical cocrystals

Physical Chemistry

Polymorph screening

Self-assembly

Details

Title: Subtitle: A 1:1 Cocrystal of Caffeine and 2-Hydroxy-1-Naphthoic Acid Obtained via a Slurry Screening Method
Creators: Dejan-Krešimir Bučar - Chemistry Department University of Iowa Iowa City IA 52242 USA
Rodger Henry - Structural Chemistry, Global Pharmaceutics R&D, Abbott Laboratories Abbott Park IL 60064 USA
Richard Duerst - Microscopy Group, Global Pharmaceutics R&D, Abbott Laboratories Abbott Park IL 60064 USA
Xiaochun Lou - Solid State Sciences, Global Pharmaceutics R&D, Abbott Laboratories North Chicago IL 60064 USA
Leonard MacGillivray - Chemistry Department University of Iowa Iowa City IA 52242 USA
Geoff Zhang - Solid State Sciences, Global Pharmaceutics R&D, Abbott Laboratories North Chicago IL 60064 USA
Resource Type: Journal article
Publication Details: Journal of chemical crystallography, Vol.40(11), pp.933-939
Publisher: Springer US
DOI: 10.1007/s10870-010-9766-y
ISSN: 1074-1542
eISSN: 1572-8854
Language: English
Date published: 11/2010
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
Record Identifier: 9984216571202771

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