2‐Ethyl‐1‐[5‐(4‐methylphenyl)pyrazol‐3‐yl]‐3‐(thiophene‐2‐carbonyl)isothiourea: molecular ribbons containing three types of hydrogen‐bonded ring
The title compound, C18H18N4OS2, was prepared by reaction of S,S‐diethyl 2‐thenoylimidodithiocarbonate with 5‐amino‐3‐(4‐methylphenyl)‐1H‐pyrazole using microwave irradiation under solvent‐free conditions. In the molecule, the thiophene unit is disordered over two sets of atomic sites, with occupanc...
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| Veröffentlicht in: | Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2014-11, Vol.70 (11), p.1064-1068 |
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| container_issue | 11 |
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| container_title | Acta crystallographica. Section C, Crystal structure communications |
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| creator | Castro, Edison Insuasty, Henry Insuasty, Braulio Cobo, Justo Glidewell, Christopher |
| description | The title compound, C18H18N4OS2, was prepared by reaction of S,S‐diethyl 2‐thenoylimidodithiocarbonate with 5‐amino‐3‐(4‐methylphenyl)‐1H‐pyrazole using microwave irradiation under solvent‐free conditions. In the molecule, the thiophene unit is disordered over two sets of atomic sites, with occupancies of 0.814 (4) and 0.186 (4), and the bonded distances provide evidence for polarization in the acylthiourea fragment and for aromatic type delocalization in the pyrazole ring. An intramolecular N—H...O hydrogen bond is present, forming an S(6) motif, and molecules are linked by N—H...O and N—H...N hydrogen bonds to form a ribbon in which centrosymmetric R22(4) rings, built from N—H...O hydrogen bonds and flanked by inversion‐related pairs of S(6) rings, alternate with centrosymmetric R22(6) rings built from N—H...N hydrogen bonds. |
| doi_str_mv | 10.1107/S205322961402244X |
| format | Article |
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In the molecule, the thiophene unit is disordered over two sets of atomic sites, with occupancies of 0.814 (4) and 0.186 (4), and the bonded distances provide evidence for polarization in the acylthiourea fragment and for aromatic type delocalization in the pyrazole ring. An intramolecular N—H...O hydrogen bond is present, forming an S(6) motif, and molecules are linked by N—H...O and N—H...N hydrogen bonds to form a ribbon in which centrosymmetric R22(4) rings, built from N—H...O hydrogen bonds and flanked by inversion‐related pairs of S(6) rings, alternate with centrosymmetric R22(6) rings built from N—H...N hydrogen bonds.</description><identifier>ISSN: 2053-2296</identifier><identifier>ISSN: 0108-2701</identifier><identifier>EISSN: 2053-2296</identifier><identifier>EISSN: 1600-5759</identifier><identifier>DOI: 10.1107/S205322961402244X</identifier><identifier>PMID: 25370108</identifier><language>eng</language><publisher>5 Abbey Square, Chester, Cheshire CH1 2HU, England: International Union of Crystallography</publisher><subject>charge‐assisted hydrogen bonding ; Crystal structure ; Crystallography ; Crystallography, X-Ray ; Hydrogen Bonding ; Hydrogen bonds ; isothiourea ; microwave irradiation ; molecular ribbons ; pharmacological activity ; solvent‐free conditions ; thiophene ; Thiophenes - chemistry ; Thiourea - analogs & derivatives ; Thiourea - chemistry</subject><ispartof>Acta crystallographica. 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Section C, Crystal structure communications</title><addtitle>Acta Crystallogr C Struct Chem</addtitle><description>The title compound, C18H18N4OS2, was prepared by reaction of S,S‐diethyl 2‐thenoylimidodithiocarbonate with 5‐amino‐3‐(4‐methylphenyl)‐1H‐pyrazole using microwave irradiation under solvent‐free conditions. In the molecule, the thiophene unit is disordered over two sets of atomic sites, with occupancies of 0.814 (4) and 0.186 (4), and the bonded distances provide evidence for polarization in the acylthiourea fragment and for aromatic type delocalization in the pyrazole ring. An intramolecular N—H...O hydrogen bond is present, forming an S(6) motif, and molecules are linked by N—H...O and N—H...N hydrogen bonds to form a ribbon in which centrosymmetric R22(4) rings, built from N—H...O hydrogen bonds and flanked by inversion‐related pairs of S(6) rings, alternate with centrosymmetric R22(6) rings built from N—H...N hydrogen bonds.</description><subject>charge‐assisted hydrogen bonding</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Crystallography, X-Ray</subject><subject>Hydrogen Bonding</subject><subject>Hydrogen bonds</subject><subject>isothiourea</subject><subject>microwave irradiation</subject><subject>molecular ribbons</subject><subject>pharmacological activity</subject><subject>solvent‐free conditions</subject><subject>thiophene</subject><subject>Thiophenes - chemistry</subject><subject>Thiourea - analogs & derivatives</subject><subject>Thiourea - chemistry</subject><issn>2053-2296</issn><issn>0108-2701</issn><issn>2053-2296</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc2K1TAUx4MozjDOA7iRgpvr4mq-07gbLuMHDrgYBUWkpOnpbYe0qUmL1JWP4GP4XD6JCfcqogsXOefknN__T8JB6D7BjwnB6sk1xYJRqiXhmFLO391Cp7m1zb3bf9Qn6DzGG4wxIVQoRe6iEyqYwgSXp-g7_fH12-XcrS5lks4HkcKGpzBAbk8djKt7NK3BfPEZYums7uOx2sxd7zMD6ZK9rAm1z4o--jxbApinxeAd2MWZUIS-TvNYWD_Oph_7cV_MXQAo5nWCWPi26NYm-D2MySyRDTRJM-7voTutcRHOj_kMvX12-Wb3Ynv1-vnL3cXV1jJGyi0Xom6l0tqytsQNUbQ0gnAqQQqWypoKjVvDlSqN5EZogU1ty1ZJC5pZzM7Q5uA7Bf9pgThXQx8tOGdG8EusiKSEEq0xTejDv9Cb9N0xvS5TmGMiJUsUOVA2-BgDtNUU-sGEtSK4ypus_tlk0jw4Oi_1AM1vxa-9JUAfgM-9g_X_jtXF-x29fsWELNlP3Yy1eA</recordid><startdate>201411</startdate><enddate>201411</enddate><creator>Castro, Edison</creator><creator>Insuasty, Henry</creator><creator>Insuasty, Braulio</creator><creator>Cobo, Justo</creator><creator>Glidewell, Christopher</creator><general>International Union of Crystallography</general><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>201411</creationdate><title>2‐Ethyl‐1‐[5‐(4‐methylphenyl)pyrazol‐3‐yl]‐3‐(thiophene‐2‐carbonyl)isothiourea: molecular ribbons containing three types of hydrogen‐bonded ring</title><author>Castro, Edison ; Insuasty, Henry ; Insuasty, Braulio ; Cobo, Justo ; Glidewell, Christopher</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3318-455bf6799c3f80d1728a51426e6538a5b2590fa4778a64a5950abc8f76ce93c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>charge‐assisted hydrogen bonding</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Crystallography, X-Ray</topic><topic>Hydrogen Bonding</topic><topic>Hydrogen bonds</topic><topic>isothiourea</topic><topic>microwave irradiation</topic><topic>molecular ribbons</topic><topic>pharmacological activity</topic><topic>solvent‐free conditions</topic><topic>thiophene</topic><topic>Thiophenes - chemistry</topic><topic>Thiourea - analogs & derivatives</topic><topic>Thiourea - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Castro, Edison</creatorcontrib><creatorcontrib>Insuasty, Henry</creatorcontrib><creatorcontrib>Insuasty, Braulio</creatorcontrib><creatorcontrib>Cobo, Justo</creatorcontrib><creatorcontrib>Glidewell, Christopher</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Castro, Edison</au><au>Insuasty, Henry</au><au>Insuasty, Braulio</au><au>Cobo, Justo</au><au>Glidewell, Christopher</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>2‐Ethyl‐1‐[5‐(4‐methylphenyl)pyrazol‐3‐yl]‐3‐(thiophene‐2‐carbonyl)isothiourea: molecular ribbons containing three types of hydrogen‐bonded ring</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><addtitle>Acta Crystallogr C Struct Chem</addtitle><date>2014-11</date><risdate>2014</risdate><volume>70</volume><issue>11</issue><spage>1064</spage><epage>1068</epage><pages>1064-1068</pages><issn>2053-2296</issn><issn>0108-2701</issn><eissn>2053-2296</eissn><eissn>1600-5759</eissn><abstract>The title compound, C18H18N4OS2, was prepared by reaction of S,S‐diethyl 2‐thenoylimidodithiocarbonate with 5‐amino‐3‐(4‐methylphenyl)‐1H‐pyrazole using microwave irradiation under solvent‐free conditions. In the molecule, the thiophene unit is disordered over two sets of atomic sites, with occupancies of 0.814 (4) and 0.186 (4), and the bonded distances provide evidence for polarization in the acylthiourea fragment and for aromatic type delocalization in the pyrazole ring. An intramolecular N—H...O hydrogen bond is present, forming an S(6) motif, and molecules are linked by N—H...O and N—H...N hydrogen bonds to form a ribbon in which centrosymmetric R22(4) rings, built from N—H...O hydrogen bonds and flanked by inversion‐related pairs of S(6) rings, alternate with centrosymmetric R22(6) rings built from N—H...N hydrogen bonds.</abstract><cop>5 Abbey Square, Chester, Cheshire CH1 2HU, England</cop><pub>International Union of Crystallography</pub><pmid>25370108</pmid><doi>10.1107/S205322961402244X</doi><tpages>5</tpages></addata></record> |
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| ispartof | Acta crystallographica. Section C, Crystal structure communications, 2014-11, Vol.70 (11), p.1064-1068 |
| issn | 2053-2296 0108-2701 2053-2296 1600-5759 |
| language | eng |
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| source | MEDLINE; Access via Wiley Online Library; Alma/SFX Local Collection |
| subjects | charge‐assisted hydrogen bonding Crystal structure Crystallography Crystallography, X-Ray Hydrogen Bonding Hydrogen bonds isothiourea microwave irradiation molecular ribbons pharmacological activity solvent‐free conditions thiophene Thiophenes - chemistry Thiourea - analogs & derivatives Thiourea - chemistry |
| title | 2‐Ethyl‐1‐[5‐(4‐methylphenyl)pyrazol‐3‐yl]‐3‐(thiophene‐2‐carbonyl)isothiourea: molecular ribbons containing three types of hydrogen‐bonded ring |
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