Narayana, B. and Yathirajan, H. S. and Rathore, R. S. and Glidewell, Christopher (2016) Different mol\-ecular conformations co-exist in each of three 2-aryl-\it N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-di\-hydro-1\it H-pyrazol-4-yl)acetamides: hydrogen bonding in zero, one and two dimensions. Acta Crystallographica Section C, 72 (9). pp. 664-669. ISSN 2053-2296
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4-Anti\-pyrine 4-amino-1,5-dimethyl-2-phenyl-1{\it H}-pyrazol-3(2{\it H})-one and its deri{\-}vatives exhibit a range of biological activities, including analgesic, anti{\-}bacterial and anti-inflammatory, and new examples are always of potential inter{\-}est and value. 2-(4-Chloro{\-}phen{\-}yl)-{\it N}-(1,5-dimethyl-3-oxo-2-phenyl-2,3-di{\-}hydro-1{\it H}-pyrazol-4-yl)acetamide, C${\sb 19}$H${\sb 18}$ClN${\sb 3}$O${\sb 2}$, (I), crystallizes with {\it Z}{$^\prime$} = 2 in the space group {\it P}\overline{1}, whereas its positional isomer 2-(2-chloro{\-}phen{\-}yl)-{\it N}-(1,5-dimethyl-3-oxo-2-phenyl-2,3-di{\-}hydro-1{\it H}-pyrazol-4-yl)acet{\-}amide, (II), crystallizes with {\it Z}{$^\prime$} = 1 in the space group {\it C}2/{\it c}; the mol{\-}ecules of (II) are disordered over two sets of atomic sites having occupancies of 0.6020(18) and 0.3980(18). The two independent mol{\-}ecules of (I) adopt different mol{\-}ecular conformations, as do the two disorder components in (II), where the 2-chloro{\-}phenyl sub{\-}stituents adopt different orientations. The mol{\-}ecules of (I) are linked by a combination of N{---}H{$\cdots$}O and C{---}H{$\cdots$}O hydrogen bonds to form centrosymmetric four-mol{\-}ecule aggregates, while those of (II) are linked by the same types of hydrogen bonds forming sheets. The related compound {\it N}-(1,5-dimethyl-3-oxo-2-phenyl-2,3-di{\-}hydro-1{\it H}-pyrazol-4-yl)-2-(3-meth{\-}oxy{\-}phen{\-}yl)acetamide, C${\sb 20}$H${\sb 21}$N${\sb 3}$O${\sb 3}$, (III), is isomorphous with (I) but not strictly isostructural; again the two independent mol{\-}ecules adopt different mol{\-}ecular conformations, and the mol{\-}ecules are linked by N{---}H{$\cdots$}O and C{---}H{$\cdots$}O hydrogen bonds to form ribbons. Comparisons are made with some related structures, indicating that a hydrogen-bonded {\it R}${\sb 2}$${\sp 2}$(10) ring is the common structural motif.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | synthesis, molecular structure, disorder, molecular conformation, hydrogen bonding, crystal structure, acetamide, pyrazole |
| Divisions: | Department of > Chemistry |
| Depositing User: | Manjula P Library Assistant |
| Date Deposited: | 19 Jun 2019 07:27 |
| Last Modified: | 19 Jun 2019 07:27 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/3402 |
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