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Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[( E )-2-(thiophen-2-yl)ethenyl]-4,5-dihydropyridazin-3(2 H )-one
In the title compound, C 10 H 10 N 2 OS, the five atoms of the thiophene ring are essentially coplanar (r.m.s. deviation = 0.0037 Å) and the pyridazine ring is non-planar. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into dimers with an R 2 2 (8) ring motif. The dimers are link...
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| Published in: | Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2019-12, Vol.75 (12), p.1880-1883 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c354t-ebec3299bc62b30804d14ce8f225e708535deaba3b5dd787723d5015cb01a0543 |
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| cites | cdi_FETCH-LOGICAL-c354t-ebec3299bc62b30804d14ce8f225e708535deaba3b5dd787723d5015cb01a0543 |
| container_end_page | 1883 |
| container_issue | 12 |
| container_start_page | 1880 |
| container_title | Acta crystallographica. Section E, Crystallographic communications |
| container_volume | 75 |
| creator | Daoui, Said Çınar, Emine Berrin El Kalai, Fouad Saddik, Rafik Dege, Necmi Karrouchi, Khalid Benchat, Noureddine |
| description | In the title compound, C
10
H
10
N
2
OS, the five atoms of the thiophene ring are essentially coplanar (r.m.s. deviation = 0.0037 Å) and the pyridazine ring is non-planar. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into dimers with an
R
2
2
(8) ring motif. The dimers are linked by C—H...O interactions, forming layers parallel to the
bc
plane. The theoretical geometric parameters are in good agreement with XRD results. The intermolecular interactions were investigated using a Hirshfeld surface analysis and two-dimensional fingerprint plots. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H...H (39.7%), C...H/H...C (17.3%) and O...H/H...O (16.8%) contacts. |
| doi_str_mv | 10.1107/S2056989019015147 |
| format | article |
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10
H
10
N
2
OS, the five atoms of the thiophene ring are essentially coplanar (r.m.s. deviation = 0.0037 Å) and the pyridazine ring is non-planar. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into dimers with an
R
2
2
(8) ring motif. The dimers are linked by C—H...O interactions, forming layers parallel to the
bc
plane. The theoretical geometric parameters are in good agreement with XRD results. The intermolecular interactions were investigated using a Hirshfeld surface analysis and two-dimensional fingerprint plots. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H...H (39.7%), C...H/H...C (17.3%) and O...H/H...O (16.8%) contacts.</description><identifier>ISSN: 2056-9890</identifier><identifier>EISSN: 2056-9890</identifier><identifier>DOI: 10.1107/S2056989019015147</identifier><language>eng</language><publisher>International Union of Crystallography</publisher><subject>crystal structure ; dft ; dihydropyridazine ; molecular electrostatic potential ; pyridazine ; thiophen</subject><ispartof>Acta crystallographica. Section E, Crystallographic communications, 2019-12, Vol.75 (12), p.1880-1883</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c354t-ebec3299bc62b30804d14ce8f225e708535deaba3b5dd787723d5015cb01a0543</citedby><cites>FETCH-LOGICAL-c354t-ebec3299bc62b30804d14ce8f225e708535deaba3b5dd787723d5015cb01a0543</cites><orcidid>0000-0002-8075-8051 ; 0000-0003-0660-4721 ; 0000-0002-6021-8568</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Daoui, Said</creatorcontrib><creatorcontrib>Çınar, Emine Berrin</creatorcontrib><creatorcontrib>El Kalai, Fouad</creatorcontrib><creatorcontrib>Saddik, Rafik</creatorcontrib><creatorcontrib>Dege, Necmi</creatorcontrib><creatorcontrib>Karrouchi, Khalid</creatorcontrib><creatorcontrib>Benchat, Noureddine</creatorcontrib><title>Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[( E )-2-(thiophen-2-yl)ethenyl]-4,5-dihydropyridazin-3(2 H )-one</title><title>Acta crystallographica. Section E, Crystallographic communications</title><description>In the title compound, C
10
H
10
N
2
OS, the five atoms of the thiophene ring are essentially coplanar (r.m.s. deviation = 0.0037 Å) and the pyridazine ring is non-planar. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into dimers with an
R
2
2
(8) ring motif. The dimers are linked by C—H...O interactions, forming layers parallel to the
bc
plane. The theoretical geometric parameters are in good agreement with XRD results. The intermolecular interactions were investigated using a Hirshfeld surface analysis and two-dimensional fingerprint plots. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H...H (39.7%), C...H/H...C (17.3%) and O...H/H...O (16.8%) contacts.</description><subject>crystal structure</subject><subject>dft</subject><subject>dihydropyridazine</subject><subject>molecular electrostatic potential</subject><subject>pyridazine</subject><subject>thiophen</subject><issn>2056-9890</issn><issn>2056-9890</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>DOA</sourceid><recordid>eNplkctKA0EQRQdRMMR8gLteJpDWfs5jKTExgYAL40pkqH6M6TBmQvdkMa79cHuMiCAU1K1L1VncSpJrSm4oJdntEyMyLfKC0FiSiuwsGfQW7r3zP_oyGYWwI4RQIXkq2SD5nPkutFCj0Pqjbo_eTtHS-bCtbG1QOPoKtEWwh7oLLkRh0P1iE7ePxtmAmgql-GWM5miCGR63W9cctnYfdVdPbBtlV79iMZXYuG1nfHPovDPw4faYjxlaxrNmb6-SiwrqYEc_fZg8L-ab2RKvHx9Ws7s11lyKFltlNWdFoXTKFCc5EYYKbfOKMWkzkksujQUFXEljsjzLGDcyBqIVoUCk4MNkdeKaBnblwbt38F3ZgCu_jca_leBbp2tbshyAZ6lQacwK4lTwjKtKpFVOmYKeRU8s7ZsQvK1-eZSU_VfKf1_hX-zbfJc</recordid><startdate>20191201</startdate><enddate>20191201</enddate><creator>Daoui, Said</creator><creator>Çınar, Emine Berrin</creator><creator>El Kalai, Fouad</creator><creator>Saddik, Rafik</creator><creator>Dege, Necmi</creator><creator>Karrouchi, Khalid</creator><creator>Benchat, Noureddine</creator><general>International Union of Crystallography</general><scope>AAYXX</scope><scope>CITATION</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-8075-8051</orcidid><orcidid>https://orcid.org/0000-0003-0660-4721</orcidid><orcidid>https://orcid.org/0000-0002-6021-8568</orcidid></search><sort><creationdate>20191201</creationdate><title>Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[( E )-2-(thiophen-2-yl)ethenyl]-4,5-dihydropyridazin-3(2 H )-one</title><author>Daoui, Said ; Çınar, Emine Berrin ; El Kalai, Fouad ; Saddik, Rafik ; Dege, Necmi ; Karrouchi, Khalid ; Benchat, Noureddine</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c354t-ebec3299bc62b30804d14ce8f225e708535deaba3b5dd787723d5015cb01a0543</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>crystal structure</topic><topic>dft</topic><topic>dihydropyridazine</topic><topic>molecular electrostatic potential</topic><topic>pyridazine</topic><topic>thiophen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Daoui, Said</creatorcontrib><creatorcontrib>Çınar, Emine Berrin</creatorcontrib><creatorcontrib>El Kalai, Fouad</creatorcontrib><creatorcontrib>Saddik, Rafik</creatorcontrib><creatorcontrib>Dege, Necmi</creatorcontrib><creatorcontrib>Karrouchi, Khalid</creatorcontrib><creatorcontrib>Benchat, Noureddine</creatorcontrib><collection>CrossRef</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Daoui, Said</au><au>Çınar, Emine Berrin</au><au>El Kalai, Fouad</au><au>Saddik, Rafik</au><au>Dege, Necmi</au><au>Karrouchi, Khalid</au><au>Benchat, Noureddine</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[( E )-2-(thiophen-2-yl)ethenyl]-4,5-dihydropyridazin-3(2 H )-one</atitle><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle><date>2019-12-01</date><risdate>2019</risdate><volume>75</volume><issue>12</issue><spage>1880</spage><epage>1883</epage><pages>1880-1883</pages><issn>2056-9890</issn><eissn>2056-9890</eissn><abstract>In the title compound, C
10
H
10
N
2
OS, the five atoms of the thiophene ring are essentially coplanar (r.m.s. deviation = 0.0037 Å) and the pyridazine ring is non-planar. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into dimers with an
R
2
2
(8) ring motif. The dimers are linked by C—H...O interactions, forming layers parallel to the
bc
plane. The theoretical geometric parameters are in good agreement with XRD results. The intermolecular interactions were investigated using a Hirshfeld surface analysis and two-dimensional fingerprint plots. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H...H (39.7%), C...H/H...C (17.3%) and O...H/H...O (16.8%) contacts.</abstract><pub>International Union of Crystallography</pub><doi>10.1107/S2056989019015147</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-8075-8051</orcidid><orcidid>https://orcid.org/0000-0003-0660-4721</orcidid><orcidid>https://orcid.org/0000-0002-6021-8568</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | Acta crystallographica. Section E, Crystallographic communications, 2019-12, Vol.75 (12), p.1880-1883 |
| issn | 2056-9890 2056-9890 |
| language | eng |
| recordid | cdi_doaj_primary_oai_doaj_org_article_28aa3764b6014a28a9373bf46f812ba4 |
| source | Open Access: PubMed Central |
| subjects | crystal structure dft dihydropyridazine molecular electrostatic potential pyridazine thiophen |
| title | Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[( E )-2-(thiophen-2-yl)ethenyl]-4,5-dihydropyridazin-3(2 H )-one |
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