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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...

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Autores principales: Pires, Fabrício Carvalho, Bresolin, Leandro, Gervini, Vanessa Carratu, Tirloni, Bárbara, Bof de Oliveira, Adriano
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
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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.
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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
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