The 1:1 co-crystal of 2-bromonaphthalene-1,4-dione and 1,8-dihydroxyanthracene-9,10-dione: crystal structure and Hirshfeld surface analysis
The asymmetric unit of the title co-crystal, C10H5BrO2·C14H8O4 [systematic name: 2-bromo-1,4-dihydronaphthalene-1,4-dione–1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (1/1)], features one molecule of each coformer. The 2-bromonaphthoquinone molecule is almost planar [r.m.s deviation of the 13 non...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2017-05-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989017005667 |
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| author | Marlon D. L. Tonin Simon J. Garden Mukesh M. Jotani Solange M. S. V. Wardell James L. Wardell Edward R. T. Tiekink |
| author_facet | Marlon D. L. Tonin Simon J. Garden Mukesh M. Jotani Solange M. S. V. Wardell James L. Wardell Edward R. T. Tiekink |
| author_sort | Marlon D. L. Tonin |
| collection | DOAJ |
| description | The asymmetric unit of the title co-crystal, C10H5BrO2·C14H8O4 [systematic name: 2-bromo-1,4-dihydronaphthalene-1,4-dione–1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (1/1)], features one molecule of each coformer. The 2-bromonaphthoquinone molecule is almost planar [r.m.s deviation of the 13 non-H atoms = 0.060 Å, with the maximum deviations of 0.093 (1) and 0.099 (1) Å being for the Br atom and a carbonyl-O atom, respectively]. The 1,8-dihydroxyanthraquinone molecule is planar (r.m.s. deviation for the 18 non-H atoms is 0.022 Å) and features two intramolecular hydroxy-O—H...O(carbonyl) hydrogen bonds. Dimeric aggregates of 1,8-dihydroxyanthraquinone molecules assemble through weak intermolecular hydroxy-O—H...O(carbonyl) hydrogen bonds. The molecular packing comprises stacks of molecules of 2-bromonaphthoquinone and dimeric assembles of 1,8-dihydroxyanthraquinone with the shortest π–π contact within a stack of 3.5760 (9) Å occurring between the different rings of 2-bromonaphthoquinone molecules. The analysis of the Hirshfeld surface reveals the importance of the interactions just indicated but, also the contribution of additional C—H...O contacts as well as C=O...π interactions to the molecular packing. |
| first_indexed | 2024-12-20T21:48:23Z |
| format | Article |
| id | doaj.art-de65e9d53f9e407e9a9e38c6f02c6f81 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-20T21:48:23Z |
| publishDate | 2017-05-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-de65e9d53f9e407e9a9e38c6f02c6f812022-12-21T19:25:37ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902017-05-0173573874510.1107/S2056989017005667wm5383The 1:1 co-crystal of 2-bromonaphthalene-1,4-dione and 1,8-dihydroxyanthracene-9,10-dione: crystal structure and Hirshfeld surface analysisMarlon D. L. Tonin0Simon J. Garden1Mukesh M. Jotani2Solange M. S. V. Wardell3James L. Wardell4Edward R. T. Tiekink5Instituto de Química, Universidade Federal do Rio de Janeiro, Centro Tecnológica, Bloco A, Cidade Universitária, Ilha do Fundão, 21949-909 Rio de Janeiro, RJ, BrazilInstituto de Química, Universidade Federal do Rio de Janeiro, Centro Tecnológica, Bloco A, Cidade Universitária, Ilha do Fundão, 21949-909 Rio de Janeiro, RJ, BrazilDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380 001, IndiaCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, ScotlandFundaçaö Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far Manguinhos, 21041-250 Rio de Janeiro, RJ, BrazilResearch Centre for Chemical Crystallography, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, MalaysiaThe asymmetric unit of the title co-crystal, C10H5BrO2·C14H8O4 [systematic name: 2-bromo-1,4-dihydronaphthalene-1,4-dione–1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (1/1)], features one molecule of each coformer. The 2-bromonaphthoquinone molecule is almost planar [r.m.s deviation of the 13 non-H atoms = 0.060 Å, with the maximum deviations of 0.093 (1) and 0.099 (1) Å being for the Br atom and a carbonyl-O atom, respectively]. The 1,8-dihydroxyanthraquinone molecule is planar (r.m.s. deviation for the 18 non-H atoms is 0.022 Å) and features two intramolecular hydroxy-O—H...O(carbonyl) hydrogen bonds. Dimeric aggregates of 1,8-dihydroxyanthraquinone molecules assemble through weak intermolecular hydroxy-O—H...O(carbonyl) hydrogen bonds. The molecular packing comprises stacks of molecules of 2-bromonaphthoquinone and dimeric assembles of 1,8-dihydroxyanthraquinone with the shortest π–π contact within a stack of 3.5760 (9) Å occurring between the different rings of 2-bromonaphthoquinone molecules. The analysis of the Hirshfeld surface reveals the importance of the interactions just indicated but, also the contribution of additional C—H...O contacts as well as C=O...π interactions to the molecular packing.http://scripts.iucr.org/cgi-bin/paper?S2056989017005667crystal structureco-crystalnaphthalene-1,4-dionedihydroxyanthracene-9,10-dioneHirshfeld surface analysis |
| spellingShingle | Marlon D. L. Tonin Simon J. Garden Mukesh M. Jotani Solange M. S. V. Wardell James L. Wardell Edward R. T. Tiekink The 1:1 co-crystal of 2-bromonaphthalene-1,4-dione and 1,8-dihydroxyanthracene-9,10-dione: crystal structure and Hirshfeld surface analysis Acta Crystallographica Section E: Crystallographic Communications crystal structure co-crystal naphthalene-1,4-dione dihydroxyanthracene-9,10-dione Hirshfeld surface analysis |
| title | The 1:1 co-crystal of 2-bromonaphthalene-1,4-dione and 1,8-dihydroxyanthracene-9,10-dione: crystal structure and Hirshfeld surface analysis |
| title_full | The 1:1 co-crystal of 2-bromonaphthalene-1,4-dione and 1,8-dihydroxyanthracene-9,10-dione: crystal structure and Hirshfeld surface analysis |
| title_fullStr | The 1:1 co-crystal of 2-bromonaphthalene-1,4-dione and 1,8-dihydroxyanthracene-9,10-dione: crystal structure and Hirshfeld surface analysis |
| title_full_unstemmed | The 1:1 co-crystal of 2-bromonaphthalene-1,4-dione and 1,8-dihydroxyanthracene-9,10-dione: crystal structure and Hirshfeld surface analysis |
| title_short | The 1:1 co-crystal of 2-bromonaphthalene-1,4-dione and 1,8-dihydroxyanthracene-9,10-dione: crystal structure and Hirshfeld surface analysis |
| title_sort | 1 1 co crystal of 2 bromonaphthalene 1 4 dione and 1 8 dihydroxyanthracene 9 10 dione crystal structure and hirshfeld surface analysis |
| topic | crystal structure co-crystal naphthalene-1,4-dione dihydroxyanthracene-9,10-dione Hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989017005667 |
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