Crystal structures and Hirshfeld surface analyses of methyl (2<i>Z</i>)-(4-bromophenyl)[2-(4-methylphenyl)hydrazinylidene]acetate, methyl (2<i>Z</i>)-(4-bromophenyl)[2-(3,5-dimethylphenyl)hydrazinylidene]acetate, methyl (2<i>Z</i>)-[2-(4-methoxypheny
Mol-ecules of the title compounds, methyl (<i>Z</i>)-2-(4-bromo-phen-yl)-2-[2-(4-methyl-phen-yl)hydrazin-1-yl-idene]acetate, C<sub>16</sub>H<sub>15</sub>BrN<sub>2</sub>O <sub><i>2</i></sub> , (<b>1</b>), methyl (<i>Z</i>)-2-(4-bromo-phen-yl)-2-[2-(3,5-di-methyl-phen-yl)hydrazin-1-yl-idene]acetate, C<sub>17</sub>H<sub>17</sub>BrN<sub>2</sub>O<sub>2</sub>, (<b>2</b>), methyl (<i>Z</i>)-2-[2-(4-meth-oxy-phen-yl)hydrazin-1-yl-idene]-2-(3-nitro-phen-yl)acetate, C<sub>16</sub>H<sub>15</sub>N<sub>3</sub>O<sub>5</sub>, (<b>3</b>), and methyl (<i>Z</i>)-2-[2-(4-bromo-phen-yl)hydrazin-1-yl-idene]-2-(4-chloro-phen-yl)acetate, C<sub>15</sub>H<sub>12</sub>BrClN<sub>2</sub>O<sub>2</sub>, (<b>5</b>), adopt a <i>Z</i> configuration with respect to the central C=N bond, while methyl (<i>E</i>)-2-(4-chloro-phen-yl)-2-(2-phenyl-hydrazin-1-yl-idene)acetate, C<sub>15</sub>H<sub>13</sub>ClN<sub>2</sub>O<sub>2</sub>, (<b>4</b>), adopts an <i>E</i> configuration. The atoms of the phenyl ring of the bromo-phenyl group of (<b>1</b>) are disordered over two sets of sites with equal occupancies. In the crystal structure of (<b>1</b>), mol-ecules connected by C-H⋯N hydrogen bonds are further linked by C-H⋯π inter-actions, forming ribbons parallel to [010]. In (<b>2</b>), pairs of mol-ecules are linked by C-H⋯π inter-actions parallel to [100]. In (<b>3</b>), C-H⋯O hydrogen bonds form ribbons parallel to [010], while in (<b>4</b>), the mol-ecules are bonded together by C-H⋯N, C-H⋯Cl, C-H⋯O and C-H⋯π inter-actions parallel to [010]. In (<b>5</b>), C-H⋯Br, C-H⋯O and C-H⋯Cl inter-actions lead to the formation of layers parallel to (002). C-H⋯π inter-actions also occur between these planes. Hirshfeld surface analyses were performed to investigate and qu-antify the inter-molecular inter-actions between the mol-ecules of all compounds.
Authors
- Zeliha Atioğlu (ORCID: https://orcid.org/0000-0002-1141-5151)
- Namiq Q. Shikhaliyev (ORCID: https://orcid.org/0000-0002-6842-151X)
- Victor N. Khrustalev (ORCID: https://orcid.org/0000-0001-8806-2975)
- Aliyar A. Babazade
- Ajaya Bhattarai (ORCID: https://orcid.org/0000-0002-2648-4686)
- Irada M. Shikhaliyeva
- Gulnar T. Atakishiyeva
- Mehmet Akkurt (ORCID: https://orcid.org/0000-0003-2421-0929)
- Abel M. Maharramov (ORCID: https://orcid.org/0000-0003-1882-7519)
Institutions
- Peoples' Friendship University of Russia (RU)
- Tribhuvan University (NP)
- Baku State University (AZ)
- N.D. Zelinsky Institute of Organic Chemistry (RU)
- Cappadocia University (TR)
- Baku Engineering University (AZ)
- Erciyes University (TR)
Publication Details
- Journal
- Acta Crystallographica Section E Crystallographic Communications
- Published
- 2025-03-14
- DOI
- https://doi.org/10.1107/s2056989025002051
- Primary Topic
- Crystal structures of chemical compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00