Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoate
The title compound, C15H10ClNO5, is relatively planar with the two aromatic rings being inclined to each other by 3.56 (11)°. The central —C(=O)—C–O—C(=O)— bridge is slightly twisted, with a C—C—O—C torsion angle of 164.95 (16)°. In the crystal, molecules are linked by C—H...O and C—H...Cl hydrogen...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019-11-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019014336 |
| _version_ | 1798024631138910208 |
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| author | S. N. Sheshadri C. S. Chidan Kumar S. Naveen M. K. Veeraiah Kakarla Raghava Reddy Ismail Warad |
| author_facet | S. N. Sheshadri C. S. Chidan Kumar S. Naveen M. K. Veeraiah Kakarla Raghava Reddy Ismail Warad |
| author_sort | S. N. Sheshadri |
| collection | DOAJ |
| description | The title compound, C15H10ClNO5, is relatively planar with the two aromatic rings being inclined to each other by 3.56 (11)°. The central —C(=O)—C–O—C(=O)— bridge is slightly twisted, with a C—C—O—C torsion angle of 164.95 (16)°. In the crystal, molecules are linked by C—H...O and C—H...Cl hydrogen bonds, forming layers parallel to the (101) plane. The layers are linked by a further C—H...O hydrogen bond, forming a three-dimensional supramolecular structure. There are a number of offset π–π interactions present between the layers [intercentroid distances vary from 3.8264 (15) to 3.9775 (14) Å]. Hirshfeld surface analyses, the dnorm surfaces, electrostatic potential and two-dimensional fingerprint plots were examined to verify the contributions of the different intermolecular contacts within the supramolecular structure. The shape-index surface shows that two sides of the molecule are involved in the same contacts with neighbouring molecules, and the curvedness plot shows flat surface patches that are characteristic of planar stacking. |
| first_indexed | 2024-04-11T18:05:42Z |
| format | Article |
| id | doaj.art-caa4e26e7b164e969df244eb16438bf9 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T18:05:42Z |
| publishDate | 2019-11-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-caa4e26e7b164e969df244eb16438bf92022-12-22T04:10:21ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-11-0175111792179610.1107/S2056989019014336su5521Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoateS. N. Sheshadri0C. S. Chidan Kumar1S. Naveen2M. K. Veeraiah3Kakarla Raghava Reddy4Ismail Warad5Department of Chemistry, GSSS Institute of Engineering and Technology for Women, Mysuru 570 016, Karnataka, IndiaDepartment of Engineering Chemistry, Vidya Vikas Institute of, Engineering & Technology, Visvesvaraya Technological University, Alanahally, Mysuru 570 028, Karnataka, IndiaDepartment of Physics, School of Engineering and Technology, Jain University, Bangalore 562 112, IndiaDepartment of Chemistry, Sri Siddhartha Institute of Technology, Tumkur 572 105, Karnataka, IndiaSchool of Chemical & Biomolecular Engineering, The University of Sydney, Sydney, NSW, AustraliaDepartment of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian TerritoriesThe title compound, C15H10ClNO5, is relatively planar with the two aromatic rings being inclined to each other by 3.56 (11)°. The central —C(=O)—C–O—C(=O)— bridge is slightly twisted, with a C—C—O—C torsion angle of 164.95 (16)°. In the crystal, molecules are linked by C—H...O and C—H...Cl hydrogen bonds, forming layers parallel to the (101) plane. The layers are linked by a further C—H...O hydrogen bond, forming a three-dimensional supramolecular structure. There are a number of offset π–π interactions present between the layers [intercentroid distances vary from 3.8264 (15) to 3.9775 (14) Å]. Hirshfeld surface analyses, the dnorm surfaces, electrostatic potential and two-dimensional fingerprint plots were examined to verify the contributions of the different intermolecular contacts within the supramolecular structure. The shape-index surface shows that two sides of the molecule are involved in the same contacts with neighbouring molecules, and the curvedness plot shows flat surface patches that are characteristic of planar stacking.http://scripts.iucr.org/cgi-bin/paper?S2056989019014336crystal structuresupramolecular architecturec—h...cl hydrogen bondsπ–π interactionshirshfeld surface analysis |
| spellingShingle | S. N. Sheshadri C. S. Chidan Kumar S. Naveen M. K. Veeraiah Kakarla Raghava Reddy Ismail Warad Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoate Acta Crystallographica Section E: Crystallographic Communications crystal structure supramolecular architecture c—h...cl hydrogen bonds π–π interactions hirshfeld surface analysis |
| title | Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoate |
| title_full | Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoate |
| title_fullStr | Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoate |
| title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoate |
| title_short | Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoate |
| title_sort | crystal structure and hirshfeld surface analysis of 2 4 nitrophenyl 2 oxoethyl 2 chlorobenzoate |
| topic | crystal structure supramolecular architecture c—h...cl hydrogen bonds π–π interactions hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019014336 |
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