Cargando…
Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1R,4S)- and 1-[(1S,4R)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide
The equimolar reaction between a racemic mixture of (R)- and (S)-camphorquinone with thiosemicarbazide yielded the title compound, C(11)H(17)N(3)OS [common name: (R)- and (S)-camphor thiosemicarbazone], which maintains the chirality of the methylated chiral carbon atoms and crystallizes in the ce...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6944080/ https://www.ncbi.nlm.nih.gov/pubmed/31921463 http://dx.doi.org/10.1107/S2056989019016980 |
_version_ | 1783484990094311424 |
---|---|
author | Pires, Fabrício Carvalho Bresolin, Leandro Gervini, Vanessa Carratu Tirloni, Bárbara Bof de Oliveira, Adriano |
author_facet | Pires, Fabrício Carvalho Bresolin, Leandro Gervini, Vanessa Carratu Tirloni, Bárbara Bof de Oliveira, Adriano |
author_sort | Pires, Fabrício Carvalho |
collection | PubMed |
description | The equimolar reaction between a racemic mixture of (R)- and (S)-camphorquinone with thiosemicarbazide yielded the title compound, C(11)H(17)N(3)OS [common name: (R)- and (S)-camphor thiosemicarbazone], which maintains the chirality of the methylated chiral carbon atoms and crystallizes in the centrosymmetric space group C2/c. There are two molecules in general positions in the asymmetric unit, one of them being the (1R)-camphor thiosemicarbazone isomer and the second the (1S)- isomer. In the crystal, the molecular units are linked by C—H⋯S, N—H⋯O and N—H⋯S interactions, building a tape-like structure parallel to the ([Image: see text]01) plane, generating R (2) (1)(7) and R (2) (2)(8) graph-set motifs for the H⋯S interactions. The Hirshfeld surface analysis indicates that the major contributions for crystal cohesion are from H⋯H (55.00%), H⋯S (22.00%), H⋯N (8.90%) and H⋯O (8.40%) interactions. |
format | Online Article Text |
id | pubmed-6944080 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-69440802020-01-09 Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1R,4S)- and 1-[(1S,4R)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide Pires, Fabrício Carvalho Bresolin, Leandro Gervini, Vanessa Carratu Tirloni, Bárbara Bof de Oliveira, Adriano Acta Crystallogr E Crystallogr Commun Research Communications The equimolar reaction between a racemic mixture of (R)- and (S)-camphorquinone with thiosemicarbazide yielded the title compound, C(11)H(17)N(3)OS [common name: (R)- and (S)-camphor thiosemicarbazone], which maintains the chirality of the methylated chiral carbon atoms and crystallizes in the centrosymmetric space group C2/c. There are two molecules in general positions in the asymmetric unit, one of them being the (1R)-camphor thiosemicarbazone isomer and the second the (1S)- isomer. In the crystal, the molecular units are linked by C—H⋯S, N—H⋯O and N—H⋯S interactions, building a tape-like structure parallel to the ([Image: see text]01) plane, generating R (2) (1)(7) and R (2) (2)(8) graph-set motifs for the H⋯S interactions. The Hirshfeld surface analysis indicates that the major contributions for crystal cohesion are from H⋯H (55.00%), H⋯S (22.00%), H⋯N (8.90%) and H⋯O (8.40%) interactions. International Union of Crystallography 2020-01-01 /pmc/articles/PMC6944080/ /pubmed/31921463 http://dx.doi.org/10.1107/S2056989019016980 Text en © Pires et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Pires, Fabrício Carvalho Bresolin, Leandro Gervini, Vanessa Carratu Tirloni, Bárbara Bof de Oliveira, Adriano Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1R,4S)- and 1-[(1S,4R)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide |
title | Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1R,4S)- and 1-[(1S,4R)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide |
title_full | Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1R,4S)- and 1-[(1S,4R)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide |
title_fullStr | Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1R,4S)- and 1-[(1S,4R)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide |
title_full_unstemmed | Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1R,4S)- and 1-[(1S,4R)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide |
title_short | Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1R,4S)- and 1-[(1S,4R)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide |
title_sort | synthesis, crystal structure and hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1r,4s)- and 1-[(1s,4r)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6944080/ https://www.ncbi.nlm.nih.gov/pubmed/31921463 http://dx.doi.org/10.1107/S2056989019016980 |
work_keys_str_mv | AT piresfabriciocarvalho synthesiscrystalstructureandhirshfeldanalysisofacrystallinecompoundcomprisinga11mixtureof11r4sand11s4r177trimethyl2oxobicyclo221heptan3ylidenehydrazinecarbothioamide AT bresolinleandro synthesiscrystalstructureandhirshfeldanalysisofacrystallinecompoundcomprisinga11mixtureof11r4sand11s4r177trimethyl2oxobicyclo221heptan3ylidenehydrazinecarbothioamide AT gervinivanessacarratu synthesiscrystalstructureandhirshfeldanalysisofacrystallinecompoundcomprisinga11mixtureof11r4sand11s4r177trimethyl2oxobicyclo221heptan3ylidenehydrazinecarbothioamide AT tirlonibarbara synthesiscrystalstructureandhirshfeldanalysisofacrystallinecompoundcomprisinga11mixtureof11r4sand11s4r177trimethyl2oxobicyclo221heptan3ylidenehydrazinecarbothioamide AT bofdeoliveiraadriano synthesiscrystalstructureandhirshfeldanalysisofacrystallinecompoundcomprisinga11mixtureof11r4sand11s4r177trimethyl2oxobicyclo221heptan3ylidenehydrazinecarbothioamide |