Crystal Structures of (5RS)-(Z)-4-[5-(furan-2-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-4-oxobut-2-enoic Acid and (5RS)-(Z)-4-[5-(furan-2-yl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-oxobut-2-enoic Acid Full article
Journal |
Acta Crystallographica Section E
, E-ISSN: 2056-9890 |
||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Output data | Year: 2016, Volume: 72, Number: 11, Pages: 1557-1561 Pages count : 5 DOI: 10.1107/s2056989016013992 | ||||||||||
Tags | crystal structure; furan; intramolecular Diels-Alder reaction; thiophene | ||||||||||
Authors |
|
||||||||||
Affiliations |
|
Abstract:
The title compounds, C17H14N2O4 (I) and C15H12N2O4S (II), possess very similar molecular geometries. In both molecules, the central 1,3,5-trisubstituted dihydropyrazole ring adopts an envelope conformation. The oxobutenoic acid fragment has an almost planar Z conformation [r.m.s. deviations of 0.049 and 0.022 Å, respectively, for (I) and (II)] which is determined by the both bond conjugation and the strong intramolecular O-H...O hydrogen bond. The substituents in positions 1 and 3 of the dihydropyrazole ring [oxobutenoic acid and phenyl in (I) and oxobutenoic acid and thienyl in (II)] are nearly coplanar with its basal plane [the corresponding dihedral angles are 6.14 (9) and 2.22 (11)° in (I) and 6.27 (12) and 3.91 (11)° in (II)]. The furyl ring plane is twisted relative to the basal plane of the dihydropyrazole ring by 85.51 (8) and 88.30 (7)° in (I) and (II), respectively. In the crystal of (I), molecules form zigzag hydrogen-bonded chains along [001] by C-H...O hydrogen bonds, which are further packed in stacks along [100]. Unlike (I), the crystal of (II) contains centrosymmetric hydrogen-bonded dimers formed by pairs of C-H...S hydrogen bonds, which are further linked by weak C-H...O hydrogen bonds into a three-dimensional framework.
Cite:
Borisova K.K.
, Toze F.A.A.
, Yagafarov N.Z.
, Zubkov F.I.
, Dorovatovskii P.V.
, Zubavichus Y.V.
, Khrustalev V.N.
Crystal Structures of (5RS)-(Z)-4-[5-(furan-2-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-4-oxobut-2-enoic Acid and (5RS)-(Z)-4-[5-(furan-2-yl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-oxobut-2-enoic Acid
Acta Crystallographica Section E. 2016. V.72. N11. P.1557-1561. DOI: 10.1107/s2056989016013992 WOS Scopus
Crystal Structures of (5RS)-(Z)-4-[5-(furan-2-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-4-oxobut-2-enoic Acid and (5RS)-(Z)-4-[5-(furan-2-yl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-oxobut-2-enoic Acid
Acta Crystallographica Section E. 2016. V.72. N11. P.1557-1561. DOI: 10.1107/s2056989016013992 WOS Scopus
Files:
Full text from publisher
Dates:
Submitted: | Aug 17, 2016 |
Accepted: | Sep 1, 2016 |
Published online: | Oct 11, 2016 |
Published print: | Nov 1, 2016 |
Identifiers:
Web of science | WOS:000385461500011 |
Scopus | 2-s2.0-84994391831 |
Chemical Abstracts | 2016:1787247 |
OpenAlex | W2531208516 |
Citing:
Пока нет цитирований