A Novel Crystal form of Metacetamol: The First Example of a Hydrated Form | Sciact - CRIS-system of Boreskov Institute of Catalysis

A Novel Crystal form of Metacetamol: The First Example of a Hydrated Form Full article

Journal

Acta Crystallographica Section C
, E-ISSN: 2053-2296

Output data

Year: 2019, Volume: 75, Number: 11, Pages: 1465-1470 Pages count : 6 DOI: 10.1107/s2053229619012981

Tags

hydrate; metacetamol; API; crystallization; crystal structure; crystal packing; motif; hydrogen bond; disorder

Authors

Zemtsova Viktoria M. ^1,2 , Fedorov Alexey Yu. ^1,2 , Fedorova Elizaveta A. ³ , Boa Callum ⁴ , Arkhipov Sergey G. ^1,3 , Rychkov Denis A. ^1,2 , Minkov Vasily S. ⁵ , Pulham Colin R. ⁴ , Boldyreva Elena V. ^1,3

Affiliations

1	Novosibirsk State University, Pirogova str. 2, Novosibirsk 630090, Russian Federation
2	Institute of Solid State Chemistry and Mechanochemistry SB RAS, Kutateladze str. 18, Novosibirsk 630128, Russian Federation
3	Boreskov Institute of Catalysis SB RAS, Lavrentiev Ave. 5, Novosibirsk 630090, Russian Federation
4	The University of Edinburgh, School of Chemistry, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, Scotland
5	Max-Planck Institute for Chemistry, Hahn-Meitner-Weg 1, Mainz 55128, Germany

Funding (3)

1	Federal Agency for Scientific Organizations	0301-2016-0014 (АААА-А17-117030310274-5)
2	Ministry of Science and Higher Education of the Russian Federation	0239-2019-0003
3	The University of Edinburgh

We report the crystal structure and crystallization conditions of a first hydrated form of metacetamol (a hemihydrate), C8H9NO2·0.5H2O. It crystallizes from metacetamol-saturated 1:1 (v/v) water–ethanol solutions in a monoclinic structure (space group P21/n) and contains eight metacetamol and four water molecules per unit cell. The conformations of the molecules are the same as in polymorph II of metacetamol, which ensures the formation of hydrogen-bonded dimers and R22(16) ring motifs in its crystal structure similar to those in polymorph II. Unlike in form II, however, these dimers in the hemihydrate are connected through water molecules into infinite hydrogen-bonded molecular chains. Different chains are linked to each other by metacetamol–water and metacetamol–metacetamol hydrogen bonds, the latter type being also present in polymorph I. The overall noncovalent network of the hemihydrate is well developed and several types of hydrogen bonds are responsible for its formation

Zemtsova V.M. , Fedorov A.Y. , Fedorova E.A. , Boa C. , Arkhipov S.G. , Rychkov D.A. , Minkov V.S. , Pulham C.R. , Boldyreva E.V.
A Novel Crystal form of Metacetamol: The First Example of a Hydrated Form
Acta Crystallographica Section C. 2019. V.75. N11. P.1465-1470. DOI: 10.1107/s2053229619012981 WOS Scopus РИНЦ AN PMID OpenAlex

Submitted:	Jul 23, 2019
Accepted:	Sep 19, 2019
Published online:	Oct 4, 2019
Published print:	Nov 1, 2019

Web of science:	WOS:000495393600004
Scopus:	2-s2.0-85074548259
Elibrary:	41700108
Chemical Abstracts:	2019:2093607
PMID:	31686655
OpenAlex:	W2977518381

DB	Citing
Scopus	4
Web of science	4
Elibrary	3
OpenAlex	4