Research output: Contribution to journal › Article › peer-review
A novel crystal form of metacetamol : The first example of a hydrated form. / Zemtsova, Viktoria M.; Fedorov, Alexey Yu; Fedorova, Elizaveta A. et al.
In: Acta Crystallographica Section C: Structural Chemistry, Vol. 75, 01.11.2019, p. 1465-1470.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - A novel crystal form of metacetamol
T2 - The first example of a hydrated form
AU - Zemtsova, Viktoria M.
AU - Fedorov, Alexey Yu
AU - Fedorova, Elizaveta A.
AU - Boa, Callum
AU - Arkhipov, Sergey G.
AU - Rychkov, Denis A.
AU - Minkov, Vasily S.
AU - Pulhamd, Colin R.
AU - Boldyreva, Elena V.
N1 - Publisher Copyright: © 2019 International Union of Crystallography.
PY - 2019/11/1
Y1 - 2019/11/1
N2 - We report the crystal structure and crystallization conditions of a first hydrated form of metacetamol (a hemihydrate), C8H9ONO2·0.5H2O. 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 R 2 2(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.
AB - We report the crystal structure and crystallization conditions of a first hydrated form of metacetamol (a hemihydrate), C8H9ONO2·0.5H2O. 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 R 2 2(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.
KW - ACETAMINOPHEN
KW - API
KW - PARACETAMOL
KW - SOLUBILITY
KW - crystal packing
KW - crystal structure
KW - crystallization
KW - disorder
KW - hydrate
KW - hydrogen bond
KW - metacetamol
KW - motif
UR - http://www.scopus.com/inward/record.url?scp=85074548259&partnerID=8YFLogxK
U2 - 10.1107/S2053229619012981
DO - 10.1107/S2053229619012981
M3 - Article
C2 - 31686655
AN - SCOPUS:85074548259
VL - 75
SP - 1465
EP - 1470
JO - Acta Crystallographica Section C: Structural Chemistry
JF - Acta Crystallographica Section C: Structural Chemistry
SN - 2053-2296
ER -
ID: 22335463