Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide
In the title compound, C16H14N2O3S, the 1,3-benzoxazole ring system is essentially planar (r.m.s deviation = 0.004 Å) and makes a dihedral angle of 66.16 (17)° with the benzene ring of the methoxyphenyl group. Two intramolecular N—H...O and N—H...N hydrogen bonds occur, forming S(5) and S(7) ring mo...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2019-10-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019012908 |
| _version_ | 1819001266594906112 |
|---|---|
| author | Abdullah Aydin Sevim Turktekin Celikesir Mehmet Akkurt Merve Saylam Varol Pabuccuoglu |
| author_facet | Abdullah Aydin Sevim Turktekin Celikesir Mehmet Akkurt Merve Saylam Varol Pabuccuoglu |
| author_sort | Abdullah Aydin |
| collection | DOAJ |
| description | In the title compound, C16H14N2O3S, the 1,3-benzoxazole ring system is essentially planar (r.m.s deviation = 0.004 Å) and makes a dihedral angle of 66.16 (17)° with the benzene ring of the methoxyphenyl group. Two intramolecular N—H...O and N—H...N hydrogen bonds occur, forming S(5) and S(7) ring motifs, respectively. In the crystal, pairs of C—H...O hydrogen bonds link the molecules into inversion dimers with R22(14) ring motifs, stacked along the b-axis direction. The inversion dimers are linked by C—H...π and π–π-stacking interactions [centroid-to-centroid distances = 3.631 (2) and 3.631 (2) Å], forming a three-dimensional network. Two-dimensional fingerprint plots associated with the Hirshfeld surface show that the largest contributions to the crystal packing come from H...H (39.3%), C...H/H...C (18.0%), O...H/H...O (15.6) and S...H/H...S (10.2%) interactions. |
| first_indexed | 2024-12-20T22:46:29Z |
| format | Article |
| id | doaj.art-d4c4df800fb3498299139d77363854ac |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-20T22:46:29Z |
| publishDate | 2019-10-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-d4c4df800fb3498299139d77363854ac2022-12-21T19:24:21ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-10-0175101531153510.1107/S2056989019012908rz5264Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamideAbdullah Aydin0Sevim Turktekin Celikesir1Mehmet Akkurt2Merve Saylam3Varol Pabuccuoglu4Department of Mathematics and Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, TurkeyDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, TurkeyDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Izmir Katip Celebi University, 35620 Izmir, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, 35100 Izmir, TurkeyIn the title compound, C16H14N2O3S, the 1,3-benzoxazole ring system is essentially planar (r.m.s deviation = 0.004 Å) and makes a dihedral angle of 66.16 (17)° with the benzene ring of the methoxyphenyl group. Two intramolecular N—H...O and N—H...N hydrogen bonds occur, forming S(5) and S(7) ring motifs, respectively. In the crystal, pairs of C—H...O hydrogen bonds link the molecules into inversion dimers with R22(14) ring motifs, stacked along the b-axis direction. The inversion dimers are linked by C—H...π and π–π-stacking interactions [centroid-to-centroid distances = 3.631 (2) and 3.631 (2) Å], forming a three-dimensional network. Two-dimensional fingerprint plots associated with the Hirshfeld surface show that the largest contributions to the crystal packing come from H...H (39.3%), C...H/H...C (18.0%), O...H/H...O (15.6) and S...H/H...S (10.2%) interactions.http://scripts.iucr.org/cgi-bin/paper?S2056989019012908crystal structure1,3-benzoxazole ring systemdimershydrogen bondingHirshfeld surface analysis |
| spellingShingle | Abdullah Aydin Sevim Turktekin Celikesir Mehmet Akkurt Merve Saylam Varol Pabuccuoglu Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide Acta Crystallographica Section E: Crystallographic Communications crystal structure 1,3-benzoxazole ring system dimers hydrogen bonding Hirshfeld surface analysis |
| title | Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide |
| title_full | Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide |
| title_fullStr | Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide |
| title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide |
| title_short | Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide |
| title_sort | crystal structure and hirshfeld surface analysis of 2 1 3 benzoxazol 2 yl sulfanyl n 2 methoxyphenyl acetamide |
| topic | crystal structure 1,3-benzoxazole ring system dimers hydrogen bonding Hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019012908 |
| work_keys_str_mv | AT abdullahaydin crystalstructureandhirshfeldsurfaceanalysisof213benzoxazol2ylsulfanyln2methoxyphenylacetamide AT sevimturktekincelikesir crystalstructureandhirshfeldsurfaceanalysisof213benzoxazol2ylsulfanyln2methoxyphenylacetamide AT mehmetakkurt crystalstructureandhirshfeldsurfaceanalysisof213benzoxazol2ylsulfanyln2methoxyphenylacetamide AT mervesaylam crystalstructureandhirshfeldsurfaceanalysisof213benzoxazol2ylsulfanyln2methoxyphenylacetamide AT varolpabuccuoglu crystalstructureandhirshfeldsurfaceanalysisof213benzoxazol2ylsulfanyln2methoxyphenylacetamide |