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.

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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
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article
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Crystal structures and Hirshfeld surface analyses of methyl (2Z)-(4-bromophenyl)[2-(4-methylphenyl)hydrazinylidene]acetate, methyl (2Z)-(4-bromophenyl)[2-(3,5-dimethylphenyl)hydrazinylidene]acetate, methyl (2Z)-[2-(4-methoxypheny

Zeliha Atioğlu, Namiq Q. Shikhaliyev, Victor N. Khrustalev, Aliyar A. Babazade et al.
Acta Crystallographica Section E Crystallographic Communications
Crystal structures of chemical compounds
article

Crystal structures and Hirshfeld surface analyses of methyl (2Z)-(4-bromophenyl)[2-(4-methylphenyl)hydrazinylidene]acetate, methyl (2Z)-(4-bromophenyl)[2-(3,5-dimethylphenyl)hydrazinylidene]acetate, methyl (2Z)-[2-(4-methoxypheny

Zeliha Atioğlu, Namiq Q. Shikhaliyev, Victor N. Khrustalev, Aliyar A. Babazade, Ajaya Bhattarai, Irada M. Shikhaliyeva, Gulnar T. Atakishiyeva, Mehmet Akkurt, Abel M. Maharramov
article en

Abstract

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.

Acta Crystallographica Section E Crystallographic CommunicationsVol. 81(4)
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)
Clean water and sanitation
Openalex Percentile: Top 96%
Crystal structures of chemical compounds
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