(3E)-5-Chloro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-one
The reaction between 5-cholroisatin and phenylhydrazine yields the title compound, C14H10ClN3O. The molecular structure deviates slightly from the ideal planarity, with an r.m.s. deviation of 0.1372 (12) Å for the non-H atoms. An N—H...O intramolecular interaction is observed, which supports an E co...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2016-02-01
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| Series: | IUCrData |
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| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2414314616002583 |
| _version_ | 1811269615557279744 |
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| author | Viviane C. D. Bittencourt Roberta M. F. C. Almeida Adailton J. Bortoluzzi Vanessa C. Gervini Adriano Bof de Oliveira |
| author_facet | Viviane C. D. Bittencourt Roberta M. F. C. Almeida Adailton J. Bortoluzzi Vanessa C. Gervini Adriano Bof de Oliveira |
| author_sort | Viviane C. D. Bittencourt |
| collection | DOAJ |
| description | The reaction between 5-cholroisatin and phenylhydrazine yields the title compound, C14H10ClN3O. The molecular structure deviates slightly from the ideal planarity, with an r.m.s. deviation of 0.1372 (12) Å for the non-H atoms. An N—H...O intramolecular interaction is observed, which supports an E conformation with respect to the C=N bond. In the crystal, molecules are linked by a pair of N—H...O interactions into an inversion dimer. The dimers are linked by weak C—H...Cl interactions, formng a tape structure along [101]. The tapes are also linked through a weak π–π interaction [centroid–centroid distance = 3.5773 (8) Å] into a layer parallel to (-111). An in silico evaluation of the title compound with a topoisomerase enzyme was performed and the global free energy of −26.59 kJ mol−1 was found. |
| first_indexed | 2024-04-12T21:45:17Z |
| format | Article |
| id | doaj.art-1dd090dd36bb415d961526fad1b6a768 |
| institution | Directory Open Access Journal |
| issn | 2414-3146 |
| language | English |
| last_indexed | 2024-04-12T21:45:17Z |
| publishDate | 2016-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | IUCrData |
| spelling | doaj.art-1dd090dd36bb415d961526fad1b6a7682022-12-22T03:15:39ZengInternational Union of CrystallographyIUCrData2414-31462016-02-0112x16025810.1107/S2414314616002583is5445(3E)-5-Chloro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-oneViviane C. D. Bittencourt0Roberta M. F. C. Almeida1Adailton J. Bortoluzzi2Vanessa C. Gervini3Adriano Bof de Oliveira4Escola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96203-900 Rio Grande-RS, BrazilEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96203-900 Rio Grande-RS, BrazilDepartamento de Química, Universidade Federal de Santa Catarina, Campus Universitário Trindade, 88040-900 Florianópolis-SC, BrazilEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96203-900 Rio Grande-RS, BrazilDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão-SE, BrazilThe reaction between 5-cholroisatin and phenylhydrazine yields the title compound, C14H10ClN3O. The molecular structure deviates slightly from the ideal planarity, with an r.m.s. deviation of 0.1372 (12) Å for the non-H atoms. An N—H...O intramolecular interaction is observed, which supports an E conformation with respect to the C=N bond. In the crystal, molecules are linked by a pair of N—H...O interactions into an inversion dimer. The dimers are linked by weak C—H...Cl interactions, formng a tape structure along [101]. The tapes are also linked through a weak π–π interaction [centroid–centroid distance = 3.5773 (8) Å] into a layer parallel to (-111). An in silico evaluation of the title compound with a topoisomerase enzyme was performed and the global free energy of −26.59 kJ mol−1 was found.http://scripts.iucr.org/cgi-bin/paper?S2414314616002583crystal structurechloroisatin derivativephenylhydrazone derivativetwo-dimensional hydrogen-bonded networkin silico evaluation |
| spellingShingle | Viviane C. D. Bittencourt Roberta M. F. C. Almeida Adailton J. Bortoluzzi Vanessa C. Gervini Adriano Bof de Oliveira (3E)-5-Chloro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-one IUCrData crystal structure chloroisatin derivative phenylhydrazone derivative two-dimensional hydrogen-bonded network in silico evaluation |
| title | (3E)-5-Chloro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-one |
| title_full | (3E)-5-Chloro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-one |
| title_fullStr | (3E)-5-Chloro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-one |
| title_full_unstemmed | (3E)-5-Chloro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-one |
| title_short | (3E)-5-Chloro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-one |
| title_sort | 3e 5 chloro 3 2 phenylhydrazinylidene 1h indol 2 3h one |
| topic | crystal structure chloroisatin derivative phenylhydrazone derivative two-dimensional hydrogen-bonded network in silico evaluation |
| url | http://scripts.iucr.org/cgi-bin/paper?S2414314616002583 |
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