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Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products

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Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products. / Shaibah, Mohammed A. E.; Yathirajan, Hemmige S.; ., Asma; Manju, Nagaraja; Kalluraya, Balakrishna; Rathore, Ravindranath S.; Glidewell, Christopher.

In: Acta Crystallographica Section E, Vol. 76, No. 3, 03.2020, p. 360-365.

Research output: Contribution to journalArticlepeer-review

Harvard

Shaibah, MAE, Yathirajan, HS, ., A, Manju, N, Kalluraya, B, Rathore, RS & Glidewell, C 2020, 'Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products', Acta Crystallographica Section E, vol. 76, no. 3, pp. 360-365. https://doi.org/10.1107/S2056989020001735

APA

Shaibah, M. A. E., Yathirajan, H. S., ., A., Manju, N., Kalluraya, B., Rathore, R. S., & Glidewell, C. (2020). Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products. Acta Crystallographica Section E, 76(3), 360-365. https://doi.org/10.1107/S2056989020001735

Vancouver

Shaibah MAE, Yathirajan HS, . A, Manju N, Kalluraya B, Rathore RS et al. Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products. Acta Crystallographica Section E. 2020 Mar;76(3):360-365. https://doi.org/10.1107/S2056989020001735

Author

Shaibah, Mohammed A. E. ; Yathirajan, Hemmige S. ; ., Asma ; Manju, Nagaraja ; Kalluraya, Balakrishna ; Rathore, Ravindranath S. ; Glidewell, Christopher. / Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products. In: Acta Crystallographica Section E. 2020 ; Vol. 76, No. 3. pp. 360-365.

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@article{a65be6d7ada94ca7b41802f60bdff105,
title = "Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products",
abstract = "Chalcones of type 4-XC6H4C(O)CH=CHC6H4(OCH2CCH)-4, where X = Cl, Br or MeO, have been converted to the corresponding 4,5-di­hydro­pyrazole-1-carbo­thio­amides using a cyclo­condensation reaction with thio­semicarbazide. The chalcones 1-(4-chloro­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13ClO2, (I), and 1-(4-bromo­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13BrO2, (II), are isomorphous, and their mol­ecules are linked into sheets by two independent C—Hπ(arene) inter­actions, both involving the same aryl ring with one C—H donor approaching each face. In each of the products (RS)-3-(4-chloro­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16ClN3OS, (IV), (RS)-3-(4-bromo­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16BrN3OS, (V), and (RS)-3-(4-meth­oxy­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C20H19N3O2S, (VI), the reduced pyrazole ring adopts an envelope conformation with the C atom bearing the 4-prop-2-yn­yloxy)phenyl substituent, which occupies the axial site, displaced from the plane of the four ring atoms. Compounds (IV) and (V) are isomorphous and their mol­ecules are linked into chains of edge-fused rings by a combination of N—H···S and C—H···S hydrogen bonds. The mol­ecules of (VI) are linked into sheets by a combination of N—H···S, N—H···N and C—H···π(arene) hydrogen bonds. Comparisons are made with the structures of some related compounds.",
keywords = "Synthesis, Cyclocondensation, Chalcones, Heterocyclic compounds, Reduced pyrazoles, Crystal structures, Molecular conformation, Hydrogen bonding, Supramolecular assembly",
author = "Shaibah, {Mohammed A. E.} and Yathirajan, {Hemmige S.} and Asma . and Nagaraja Manju and Balakrishna Kalluraya and Rathore, {Ravindranath S.} and Christopher Glidewell",
note = "HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.",
year = "2020",
month = mar,
doi = "10.1107/S2056989020001735",
language = "English",
volume = "76",
pages = "360--365",
journal = "Acta Crystallographica Section E Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "3",

}

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TY - JOUR

T1 - Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products

AU - Shaibah, Mohammed A. E.

AU - Yathirajan, Hemmige S.

AU - ., Asma

AU - Manju, Nagaraja

AU - Kalluraya, Balakrishna

AU - Rathore, Ravindranath S.

AU - Glidewell, Christopher

N1 - HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.

PY - 2020/3

Y1 - 2020/3

N2 - Chalcones of type 4-XC6H4C(O)CH=CHC6H4(OCH2CCH)-4, where X = Cl, Br or MeO, have been converted to the corresponding 4,5-di­hydro­pyrazole-1-carbo­thio­amides using a cyclo­condensation reaction with thio­semicarbazide. The chalcones 1-(4-chloro­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13ClO2, (I), and 1-(4-bromo­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13BrO2, (II), are isomorphous, and their mol­ecules are linked into sheets by two independent C—Hπ(arene) inter­actions, both involving the same aryl ring with one C—H donor approaching each face. In each of the products (RS)-3-(4-chloro­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16ClN3OS, (IV), (RS)-3-(4-bromo­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16BrN3OS, (V), and (RS)-3-(4-meth­oxy­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C20H19N3O2S, (VI), the reduced pyrazole ring adopts an envelope conformation with the C atom bearing the 4-prop-2-yn­yloxy)phenyl substituent, which occupies the axial site, displaced from the plane of the four ring atoms. Compounds (IV) and (V) are isomorphous and their mol­ecules are linked into chains of edge-fused rings by a combination of N—H···S and C—H···S hydrogen bonds. The mol­ecules of (VI) are linked into sheets by a combination of N—H···S, N—H···N and C—H···π(arene) hydrogen bonds. Comparisons are made with the structures of some related compounds.

AB - Chalcones of type 4-XC6H4C(O)CH=CHC6H4(OCH2CCH)-4, where X = Cl, Br or MeO, have been converted to the corresponding 4,5-di­hydro­pyrazole-1-carbo­thio­amides using a cyclo­condensation reaction with thio­semicarbazide. The chalcones 1-(4-chloro­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13ClO2, (I), and 1-(4-bromo­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13BrO2, (II), are isomorphous, and their mol­ecules are linked into sheets by two independent C—Hπ(arene) inter­actions, both involving the same aryl ring with one C—H donor approaching each face. In each of the products (RS)-3-(4-chloro­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16ClN3OS, (IV), (RS)-3-(4-bromo­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16BrN3OS, (V), and (RS)-3-(4-meth­oxy­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C20H19N3O2S, (VI), the reduced pyrazole ring adopts an envelope conformation with the C atom bearing the 4-prop-2-yn­yloxy)phenyl substituent, which occupies the axial site, displaced from the plane of the four ring atoms. Compounds (IV) and (V) are isomorphous and their mol­ecules are linked into chains of edge-fused rings by a combination of N—H···S and C—H···S hydrogen bonds. The mol­ecules of (VI) are linked into sheets by a combination of N—H···S, N—H···N and C—H···π(arene) hydrogen bonds. Comparisons are made with the structures of some related compounds.

KW - Synthesis

KW - Cyclocondensation

KW - Chalcones

KW - Heterocyclic compounds

KW - Reduced pyrazoles

KW - Crystal structures

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

U2 - 10.1107/S2056989020001735

DO - 10.1107/S2056989020001735

M3 - Article

VL - 76

SP - 360

EP - 365

JO - Acta Crystallographica Section E Crystallographic Communications

JF - Acta Crystallographica Section E Crystallographic Communications

SN - 2056-9890

IS - 3

ER -

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