A new monoclinic polymorph of N-(3-methylphenyl) ethoxycarbothioamide: Crystal structure and Hirshfeld surface analysis
The title compound, C10H13NOS, is a second monoclinic polymorph (space group P21/c, Z′ = 2) of the previously reported C2/c (Z = 1) polymorph [Tadbuppa & Tiekink (2005). Z. Kristallogr. New Cryst. Struct. 220, 395–396]. Two independent molecules comprise the asymmetric unit of the new polymorph...
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International Union of Crystallography
2017
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| Online Access: | http://eprints.sunway.edu.my/696/ http://eprints.sunway.edu.my/696/1/Tieknik%20E%20A%20new%20monoclinic%20polymorph.pdf |
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| author | Mukesh M, Yeo, Chien Ing * Tiekink, Edward R. T. * |
| author_facet | Mukesh M, Yeo, Chien Ing * Tiekink, Edward R. T. * |
| author_sort | Mukesh M, |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The title compound, C10H13NOS, is a second monoclinic polymorph (space group P21/c, Z′ = 2) of the previously reported C2/c (Z = 1) polymorph [Tadbuppa & Tiekink (2005). Z. Kristallogr. New Cryst. Struct. 220, 395–396]. Two independent molecules comprise the asymmetric unit of the new polymorph and each of these exists as a thioamide–thione tautomer. In each molecule, the central CNOS chromophore is strictly planar [r.m.s. deviations = 0.0003 and 0.0015 Å] and forms dihedral angles of 6.17 (5) and 20.78 (5)° with the N-bound 3-tolyl rings, thereby representing the major difference between the molecules. The thione-S and thioamide-N—H atoms are syn in each molecule and this facilitates the formation of an eight-membered thioamide {...SCNH}2 synthon between them; the dimeric aggregates are consolidated by pairwise 3-tolyl-C—H...S interactions. In the extended structure, supramolecular layers parallel to (102) are formed via a combination of 3-tolyl-C—H...π(3-tolyl) and weak π–π interactions [inter-centroid distance between 3-tolyl rings = 3.8535 (12) Å]. An analysis of the Hirshfeld surfaces calculated for both polymorphs reveals the near equivalence of one of the independent molecules of the P21/c form to that in the C2/c form. |
| first_indexed | 2025-11-14T21:14:28Z |
| format | Article |
| id | sunway-696 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:14:28Z |
| publishDate | 2017 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
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| spelling | sunway-6962020-10-12T07:50:49Z http://eprints.sunway.edu.my/696/ A new monoclinic polymorph of N-(3-methylphenyl) ethoxycarbothioamide: Crystal structure and Hirshfeld surface analysis Mukesh M, Yeo, Chien Ing * Tiekink, Edward R. T. * QD Chemistry The title compound, C10H13NOS, is a second monoclinic polymorph (space group P21/c, Z′ = 2) of the previously reported C2/c (Z = 1) polymorph [Tadbuppa & Tiekink (2005). Z. Kristallogr. New Cryst. Struct. 220, 395–396]. Two independent molecules comprise the asymmetric unit of the new polymorph and each of these exists as a thioamide–thione tautomer. In each molecule, the central CNOS chromophore is strictly planar [r.m.s. deviations = 0.0003 and 0.0015 Å] and forms dihedral angles of 6.17 (5) and 20.78 (5)° with the N-bound 3-tolyl rings, thereby representing the major difference between the molecules. The thione-S and thioamide-N—H atoms are syn in each molecule and this facilitates the formation of an eight-membered thioamide {...SCNH}2 synthon between them; the dimeric aggregates are consolidated by pairwise 3-tolyl-C—H...S interactions. In the extended structure, supramolecular layers parallel to (102) are formed via a combination of 3-tolyl-C—H...π(3-tolyl) and weak π–π interactions [inter-centroid distance between 3-tolyl rings = 3.8535 (12) Å]. An analysis of the Hirshfeld surfaces calculated for both polymorphs reveals the near equivalence of one of the independent molecules of the P21/c form to that in the C2/c form. International Union of Crystallography 2017 Article PeerReviewed text en http://eprints.sunway.edu.my/696/1/Tieknik%20E%20A%20new%20monoclinic%20polymorph.pdf Mukesh M, and Yeo, Chien Ing * and Tiekink, Edward R. T. * (2017) A new monoclinic polymorph of N-(3-methylphenyl) ethoxycarbothioamide: Crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E Crystallographic Communications, E73 (12). pp. 1889-1897. ISSN 2056-9890 |
| spellingShingle | QD Chemistry Mukesh M, Yeo, Chien Ing * Tiekink, Edward R. T. * A new monoclinic polymorph of N-(3-methylphenyl) ethoxycarbothioamide: Crystal structure and Hirshfeld surface analysis |
| title | A new monoclinic polymorph of N-(3-methylphenyl)
ethoxycarbothioamide: Crystal structure and
Hirshfeld surface analysis |
| title_full | A new monoclinic polymorph of N-(3-methylphenyl)
ethoxycarbothioamide: Crystal structure and
Hirshfeld surface analysis |
| title_fullStr | A new monoclinic polymorph of N-(3-methylphenyl)
ethoxycarbothioamide: Crystal structure and
Hirshfeld surface analysis |
| title_full_unstemmed | A new monoclinic polymorph of N-(3-methylphenyl)
ethoxycarbothioamide: Crystal structure and
Hirshfeld surface analysis |
| title_short | A new monoclinic polymorph of N-(3-methylphenyl)
ethoxycarbothioamide: Crystal structure and
Hirshfeld surface analysis |
| title_sort | new monoclinic polymorph of n-(3-methylphenyl)
ethoxycarbothioamide: crystal structure and
hirshfeld surface analysis |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/696/ http://eprints.sunway.edu.my/696/1/Tieknik%20E%20A%20new%20monoclinic%20polymorph.pdf |