Two N-{[4-(3-aryl-4-sydnonyl­­idene­amino)-5-sulfan­yl­­idene-1H-1,2,4-triazol-3-yl]meth­yl}benzamides as disordered ethanol monosolvates

Chayanna Harish Chinthal; Hemmige S Yathirajan; Anish Kumar Kadambar; Balakrishna Kalluraya; Sabine Foro; Christopher Glidewell

doi:10.1107/S2056989020007483

Two N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides as disordered ethanol monosolvates

Chayanna Harish Chinthal, Hemmige S Yathirajan, Anish Kumar Kadambar, Balakrishna Kalluraya, Sabine Foro, Christopher Glidewell

School of Chemistry

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Abstract

Two new N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides have been prepared by acid-promoted condensation reactions between 3-aryl-4-formylsydnones and N-[(4-amino-5-sulfanylidene-1H-1,2,4-triazol-3-yl)methyl]benzamide, and both have been crystallized as ethanol monosolvates. N-{[4-(3-Phenyl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamide ethanol monosolvate, C₁₉H₁₅N₇O₃S·C₂H₆O (I), and N-({4-[3-(4-methylphenyl)-4-sydnonylideneamino]-5-sulfanylidene-1H-1,2,4-triazol-3-yl}methyl)benzamide ethanol monosolvate, C₂₀H₁₇N₇O₃S·C₂H₆O (II), differ only in the presence of a methyl group for (II) instead of a hydrogen atom for (I), and in both of them the ethanol component is disordered over two sets of atomic sites having occupancies of 0.836 (6) and 0.164 (6) in (I), and 0.906 (6) and 0.094 (6) in (II). Combinations of O—H⋯O and N—H⋯O hydrogen bonds link the molecules into cyclic, centrosymmetric four-molecule aggregates. Comparisons are made with the structures of some related compounds.

Original language	English
Pages (from-to)	1057-1061
Number of pages	18
Journal	Acta Crystallographica Section E Crystallographic Communications
Volume	76
Issue number	Part 7
Early online date	9 Jun 2020
DOIs	https://doi.org/10.1107/S2056989020007483
Publication status	Published - Jul 2020

Keywords

1,2,4-triazoles
crystal structure
Disorder
Heterocyclic compounds
Hydrogen bonding
Supramolecular assembly
Sydnones
Synthesis

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10.1107/S2056989020007483Licence: CC BY

Chintal_2020_AC_Two_CC
Copyright © 2020 The Author(s). 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.
Final published version, 881 KBLicence: CC BY

CCDC 2007901 & 2007902: Experimental Crystal Structure Determination
Chinthal, C. H. (Creator), Yathirajan, H. S. (Creator), Kadambar, A. K. (Creator), Kalluraya, B. (Creator), Foro, S. (Creator) & Glidewell, C. (Creator), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc25dd00, https://dx.doi.org/10.5517/ccdc.csd.cc25dd11
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Cite this

Harish Chinthal, C., Yathirajan, H. S., Kadambar, A. K., Kalluraya, B., Foro, S., & Glidewell, C. (2020). Two N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides as disordered ethanol monosolvates. Acta Crystallographica Section E Crystallographic Communications, 76(Part 7), 1057-1061. https://doi.org/10.1107/S2056989020007483

@article{b609cbedc01142d190be0bf5e92ab69a,

title = "Two N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides as disordered ethanol monosolvates",

abstract = "Two new N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides have been prepared by acid-promoted condensation reactions between 3-aryl-4-formylsydnones and N-[(4-amino-5-sulfanylidene-1H-1,2,4-triazol-3-yl)methyl]benzamide, and both have been crystallized as ethanol monosolvates. N-{[4-(3-Phenyl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamide ethanol monosolvate, C19H15N7O3S·C2H6O (I), and N-({4-[3-(4-methylphenyl)-4-sydnonylideneamino]-5-sulfanylidene-1H-1,2,4-triazol-3-yl}methyl)benzamide ethanol monosolvate, C20H17N7O3S·C2H6O (II), differ only in the presence of a methyl group for (II) instead of a hydrogen atom for (I), and in both of them the ethanol component is disordered over two sets of atomic sites having occupancies of 0.836 (6) and 0.164 (6) in (I), and 0.906 (6) and 0.094 (6) in (II). Combinations of O—H⋯O and N—H⋯O hydrogen bonds link the molecules into cyclic, centrosymmetric four-molecule aggregates. Comparisons are made with the structures of some related compounds.",

keywords = "1,2,4-triazoles, crystal structure, Disorder, Heterocyclic compounds, Hydrogen bonding, Supramolecular assembly, Sydnones, Synthesis",

author = "{Harish Chinthal}, Chayanna and Yathirajan, {Hemmige S} and Kadambar, {Anish Kumar} and Balakrishna Kalluraya and Sabine Foro and Christopher Glidewell",

note = "AKK thanks the Department of Science and Technology, Government of India, for providing a Senior Research Fellowship under the DST–INSPIRE Scheme. HSY thanks the University Grants Commission, New Delhi, for the award of a BSR Faculty Fellowship for three years.",

year = "2020",

month = jul,

doi = "10.1107/S2056989020007483",

language = "English",

volume = "76",

pages = "1057--1061",

journal = "Acta Crystallographica Section E Crystallographic Communications",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "Part 7",

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Harish Chinthal, C, Yathirajan, HS, Kadambar, AK, Kalluraya, B, Foro, S & Glidewell, C 2020, 'Two N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides as disordered ethanol monosolvates', Acta Crystallographica Section E Crystallographic Communications, vol. 76, no. Part 7, pp. 1057-1061. https://doi.org/10.1107/S2056989020007483

Two N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides as disordered ethanol monosolvates. / Harish Chinthal, Chayanna; Yathirajan, Hemmige S; Kadambar, Anish Kumar et al.
In: Acta Crystallographica Section E Crystallographic Communications, Vol. 76, No. Part 7, 07.2020, p. 1057-1061.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Two N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides as disordered ethanol monosolvates

AU - Harish Chinthal, Chayanna

AU - Yathirajan, Hemmige S

AU - Kadambar, Anish Kumar

AU - Kalluraya, Balakrishna

AU - Foro, Sabine

AU - Glidewell, Christopher

N1 - AKK thanks the Department of Science and Technology, Government of India, for providing a Senior Research Fellowship under the DST–INSPIRE Scheme. HSY thanks the University Grants Commission, New Delhi, for the award of a BSR Faculty Fellowship for three years.

PY - 2020/7

Y1 - 2020/7

N2 - Two new N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides have been prepared by acid-promoted condensation reactions between 3-aryl-4-formylsydnones and N-[(4-amino-5-sulfanylidene-1H-1,2,4-triazol-3-yl)methyl]benzamide, and both have been crystallized as ethanol monosolvates. N-{[4-(3-Phenyl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamide ethanol monosolvate, C19H15N7O3S·C2H6O (I), and N-({4-[3-(4-methylphenyl)-4-sydnonylideneamino]-5-sulfanylidene-1H-1,2,4-triazol-3-yl}methyl)benzamide ethanol monosolvate, C20H17N7O3S·C2H6O (II), differ only in the presence of a methyl group for (II) instead of a hydrogen atom for (I), and in both of them the ethanol component is disordered over two sets of atomic sites having occupancies of 0.836 (6) and 0.164 (6) in (I), and 0.906 (6) and 0.094 (6) in (II). Combinations of O—H⋯O and N—H⋯O hydrogen bonds link the molecules into cyclic, centrosymmetric four-molecule aggregates. Comparisons are made with the structures of some related compounds.

AB - Two new N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides have been prepared by acid-promoted condensation reactions between 3-aryl-4-formylsydnones and N-[(4-amino-5-sulfanylidene-1H-1,2,4-triazol-3-yl)methyl]benzamide, and both have been crystallized as ethanol monosolvates. N-{[4-(3-Phenyl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamide ethanol monosolvate, C19H15N7O3S·C2H6O (I), and N-({4-[3-(4-methylphenyl)-4-sydnonylideneamino]-5-sulfanylidene-1H-1,2,4-triazol-3-yl}methyl)benzamide ethanol monosolvate, C20H17N7O3S·C2H6O (II), differ only in the presence of a methyl group for (II) instead of a hydrogen atom for (I), and in both of them the ethanol component is disordered over two sets of atomic sites having occupancies of 0.836 (6) and 0.164 (6) in (I), and 0.906 (6) and 0.094 (6) in (II). Combinations of O—H⋯O and N—H⋯O hydrogen bonds link the molecules into cyclic, centrosymmetric four-molecule aggregates. Comparisons are made with the structures of some related compounds.

KW - 1,2,4-triazoles

KW - crystal structure

KW - Disorder

KW - Heterocyclic compounds

KW - Hydrogen bonding

KW - Supramolecular assembly

KW - Sydnones

KW - Synthesis

U2 - 10.1107/S2056989020007483

DO - 10.1107/S2056989020007483

M3 - Article

C2 - 32695452

SN - 2056-9890

VL - 76

SP - 1057

EP - 1061

JO - Acta Crystallographica Section E Crystallographic Communications

JF - Acta Crystallographica Section E Crystallographic Communications

IS - Part 7

ER -

Harish Chinthal C, Yathirajan HS, Kadambar AK, Kalluraya B, Foro S, Glidewell C. Two N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides as disordered ethanol monosolvates. Acta Crystallographica Section E Crystallographic Communications. 2020 Jul;76(Part 7):1057-1061. Epub 2020 Jun 9. doi: 10.1107/S2056989020007483

Two N-{[4-(3-aryl-4-sydnonyl­­idene­amino)-5-sulfan­yl­­idene-1H-1,2,4-triazol-3-yl]meth­yl}benzamides as disordered ethanol monosolvates

Abstract

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CCDC 2007901 & 2007902: Experimental Crystal Structure Determination

Cite this

Two N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides as disordered ethanol monosolvates