The effect of hydrogen bonding on the conformations of 2-(1H-indol-3-yl)-2-oxoacetamide and 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide
In the title compounds, C10H8N2O2, (I), and C12H12N2O2, (II), the two carbonyl groups are oriented with torsion angles of −149.3 (3) and −88.55 (15)°, respectively. The single‐bond distances linking the two carbonyl groups are 1.528 (4) and 1.5298 (17) Å, respectively. In (I), the molecules are link...
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| Veröffentlicht in: | Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2012-10, Vol.68 (10), p.o405-o407 |
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| container_title | Acta crystallographica. Section C, Crystal structure communications |
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| creator | Sonar, Vijayakumar N. Parkin, Sean Crooks, Peter A. |
| description | In the title compounds, C10H8N2O2, (I), and C12H12N2O2, (II), the two carbonyl groups are oriented with torsion angles of −149.3 (3) and −88.55 (15)°, respectively. The single‐bond distances linking the two carbonyl groups are 1.528 (4) and 1.5298 (17) Å, respectively. In (I), the molecules are linked by an elaborate system of N—H...O hydrogen bonds, which form adjacent R22(8) and R42(8) ring motifs to generate a ladder‐like construct. Adjacent ladders are further linked by N—H...O hydrogen bonds to build a three‐dimensional network. The hydrogen bonding in (II) is far simpler, consisting of helical chains of N—H...O‐linked molecules that follow the 21 screw of the b axis. It is the presence of an elaborate hydrogen‐bonding system in the crystal structure of (I) that leads to the different torsion angle for the orientation of the two adjacent carbonyl groups from that in (II). |
| doi_str_mv | 10.1107/S0108270112038322 |
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Section C, Crystal structure communications</title><addtitle>Acta Cryst. C</addtitle><description>In the title compounds, C10H8N2O2, (I), and C12H12N2O2, (II), the two carbonyl groups are oriented with torsion angles of −149.3 (3) and −88.55 (15)°, respectively. The single‐bond distances linking the two carbonyl groups are 1.528 (4) and 1.5298 (17) Å, respectively. In (I), the molecules are linked by an elaborate system of N—H...O hydrogen bonds, which form adjacent R22(8) and R42(8) ring motifs to generate a ladder‐like construct. Adjacent ladders are further linked by N—H...O hydrogen bonds to build a three‐dimensional network. The hydrogen bonding in (II) is far simpler, consisting of helical chains of N—H...O‐linked molecules that follow the 21 screw of the b axis. 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Section C, Crystal structure communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sonar, Vijayakumar N.</au><au>Parkin, Sean</au><au>Crooks, Peter A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The effect of hydrogen bonding on the conformations of 2-(1H-indol-3-yl)-2-oxoacetamide and 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><addtitle>Acta Cryst. C</addtitle><date>2012-10</date><risdate>2012</risdate><volume>68</volume><issue>10</issue><spage>o405</spage><epage>o407</epage><pages>o405-o407</pages><issn>0108-2701</issn><eissn>1600-5759</eissn><abstract>In the title compounds, C10H8N2O2, (I), and C12H12N2O2, (II), the two carbonyl groups are oriented with torsion angles of −149.3 (3) and −88.55 (15)°, respectively. The single‐bond distances linking the two carbonyl groups are 1.528 (4) and 1.5298 (17) Å, respectively. In (I), the molecules are linked by an elaborate system of N—H...O hydrogen bonds, which form adjacent R22(8) and R42(8) ring motifs to generate a ladder‐like construct. Adjacent ladders are further linked by N—H...O hydrogen bonds to build a three‐dimensional network. The hydrogen bonding in (II) is far simpler, consisting of helical chains of N—H...O‐linked molecules that follow the 21 screw of the b axis. It is the presence of an elaborate hydrogen‐bonding system in the crystal structure of (I) that leads to the different torsion angle for the orientation of the two adjacent carbonyl groups from that in (II).</abstract><cop>5 Abbey Square, Chester, Cheshire CH1 2HU, England</cop><pub>International Union of Crystallography</pub><pmid>23007543</pmid><doi>10.1107/S0108270112038322</doi><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0108-2701 |
| ispartof | Acta crystallographica. Section C, Crystal structure communications, 2012-10, Vol.68 (10), p.o405-o407 |
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| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete; Alma/SFX Local Collection |
| subjects | Acetamides - chemistry Crystal structure Crystallography Crystallography, X-Ray Hydrogen Bonding Hydrogen bonds Indoles - chemistry Molecular Conformation Molecular Structure Molecules Organic Compounds |
| title | The effect of hydrogen bonding on the conformations of 2-(1H-indol-3-yl)-2-oxoacetamide and 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide |
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