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Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline
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| Zeitschriftentitel: | Acta Crystallographica Section E Crystallographic Communications |
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| Personen und Körperschaften: | , , , , , |
| In: | Acta Crystallographica Section E Crystallographic Communications, 75, 2019, 7, S. 964-968 |
| Format: | E-Article |
| Sprache: | Unbestimmt |
| veröffentlicht: |
International Union of Crystallography (IUCr)
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| Schlagwörter: |
| author_facet |
Akhramez, Soufiane Hafid, Abderrafia Khouili, Mostafa Saadi, Mohamed El Ammari, Lahcen Ketatni, El Mostafa Akhramez, Soufiane Hafid, Abderrafia Khouili, Mostafa Saadi, Mohamed El Ammari, Lahcen Ketatni, El Mostafa |
|---|---|
| author |
Akhramez, Soufiane Hafid, Abderrafia Khouili, Mostafa Saadi, Mohamed El Ammari, Lahcen Ketatni, El Mostafa |
| spellingShingle |
Akhramez, Soufiane Hafid, Abderrafia Khouili, Mostafa Saadi, Mohamed El Ammari, Lahcen Ketatni, El Mostafa Acta Crystallographica Section E Crystallographic Communications Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline Condensed Matter Physics General Materials Science General Chemistry |
| author_sort |
akhramez, soufiane |
| spelling |
Akhramez, Soufiane Hafid, Abderrafia Khouili, Mostafa Saadi, Mohamed El Ammari, Lahcen Ketatni, El Mostafa 2056-9890 International Union of Crystallography (IUCr) Condensed Matter Physics General Materials Science General Chemistry http://dx.doi.org/10.1107/s2056989019007692 <jats:p>A new quinoline-based hydrazone, C<jats:sub>16</jats:sub>H<jats:sub>12</jats:sub>ClN<jats:sub>3</jats:sub>, was synthesized by a condensation reaction of 2-chloro-3-formylquinoline with phenylhydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The molecule adopts an<jats:italic>E</jats:italic>configuration with respect to the central C=N bond. In the crystal, molecules are linked by a C—H...π-phenyl interaction, forming zigzag chains propagating along the [10\overline{3}] direction. The N—H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent molecule, so linking the chains<jats:italic>via</jats:italic>weak N—H...π interactions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (35.5%), C...H/H...C (33.7%), Cl...H/H...Cl (12.3%), N...H/H...N (9.5%) contacts.</jats:p> Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(<i>E</i>)-(2-phenylhydrazinylidene)methyl]quinoline Acta Crystallographica Section E Crystallographic Communications |
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10.1107/s2056989019007692 |
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International Union of Crystallography (IUCr), 2019 |
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International Union of Crystallography (IUCr), 2019 |
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| title |
Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_unstemmed |
Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_full |
Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_fullStr |
Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_full_unstemmed |
Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_short |
Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_sort |
synthesis, crystal structure and hirshfeld surface analysis of 2-chloro-3-[(<i>e</i>)-(2-phenylhydrazinylidene)methyl]quinoline |
| topic |
Condensed Matter Physics General Materials Science General Chemistry |
| url |
http://dx.doi.org/10.1107/s2056989019007692 |
| publishDate |
2019 |
| physical |
964-968 |
| description |
<jats:p>A new quinoline-based hydrazone, C<jats:sub>16</jats:sub>H<jats:sub>12</jats:sub>ClN<jats:sub>3</jats:sub>, was synthesized by a condensation reaction of 2-chloro-3-formylquinoline with phenylhydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The molecule adopts an<jats:italic>E</jats:italic>configuration with respect to the central C=N bond. In the crystal, molecules are linked by a C—H...π-phenyl interaction, forming zigzag chains propagating along the [10\overline{3}] direction. The N—H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent molecule, so linking the chains<jats:italic>via</jats:italic>weak N—H...π interactions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (35.5%), C...H/H...C (33.7%), Cl...H/H...Cl (12.3%), N...H/H...N (9.5%) contacts.</jats:p> |
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| author | Akhramez, Soufiane, Hafid, Abderrafia, Khouili, Mostafa, Saadi, Mohamed, El Ammari, Lahcen, Ketatni, El Mostafa |
| author_facet | Akhramez, Soufiane, Hafid, Abderrafia, Khouili, Mostafa, Saadi, Mohamed, El Ammari, Lahcen, Ketatni, El Mostafa, Akhramez, Soufiane, Hafid, Abderrafia, Khouili, Mostafa, Saadi, Mohamed, El Ammari, Lahcen, Ketatni, El Mostafa |
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| description | <jats:p>A new quinoline-based hydrazone, C<jats:sub>16</jats:sub>H<jats:sub>12</jats:sub>ClN<jats:sub>3</jats:sub>, was synthesized by a condensation reaction of 2-chloro-3-formylquinoline with phenylhydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The molecule adopts an<jats:italic>E</jats:italic>configuration with respect to the central C=N bond. In the crystal, molecules are linked by a C—H...π-phenyl interaction, forming zigzag chains propagating along the [10\overline{3}] direction. The N—H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent molecule, so linking the chains<jats:italic>via</jats:italic>weak N—H...π interactions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (35.5%), C...H/H...C (33.7%), Cl...H/H...Cl (12.3%), N...H/H...N (9.5%) contacts.</jats:p> |
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| imprint | International Union of Crystallography (IUCr), 2019 |
| imprint_str_mv | International Union of Crystallography (IUCr), 2019 |
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| mega_collection | International Union of Crystallography (IUCr) (CrossRef) |
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| spelling | Akhramez, Soufiane Hafid, Abderrafia Khouili, Mostafa Saadi, Mohamed El Ammari, Lahcen Ketatni, El Mostafa 2056-9890 International Union of Crystallography (IUCr) Condensed Matter Physics General Materials Science General Chemistry http://dx.doi.org/10.1107/s2056989019007692 <jats:p>A new quinoline-based hydrazone, C<jats:sub>16</jats:sub>H<jats:sub>12</jats:sub>ClN<jats:sub>3</jats:sub>, was synthesized by a condensation reaction of 2-chloro-3-formylquinoline with phenylhydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The molecule adopts an<jats:italic>E</jats:italic>configuration with respect to the central C=N bond. In the crystal, molecules are linked by a C—H...π-phenyl interaction, forming zigzag chains propagating along the [10\overline{3}] direction. The N—H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent molecule, so linking the chains<jats:italic>via</jats:italic>weak N—H...π interactions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (35.5%), C...H/H...C (33.7%), Cl...H/H...Cl (12.3%), N...H/H...N (9.5%) contacts.</jats:p> Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(<i>E</i>)-(2-phenylhydrazinylidene)methyl]quinoline Acta Crystallographica Section E Crystallographic Communications |
| spellingShingle | Akhramez, Soufiane, Hafid, Abderrafia, Khouili, Mostafa, Saadi, Mohamed, El Ammari, Lahcen, Ketatni, El Mostafa, Acta Crystallographica Section E Crystallographic Communications, Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline, Condensed Matter Physics, General Materials Science, General Chemistry |
| title | Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_full | Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_fullStr | Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_full_unstemmed | Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_short | Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_sort | synthesis, crystal structure and hirshfeld surface analysis of 2-chloro-3-[(<i>e</i>)-(2-phenylhydrazinylidene)methyl]quinoline |
| title_unstemmed | Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline |
| topic | Condensed Matter Physics, General Materials Science, General Chemistry |
| url | http://dx.doi.org/10.1107/s2056989019007692 |