Crystallographic and computational study of <i>t</i>-butyl <i>N</i>-[3-hydroxy-1-phenyl-4-(pyridin- 2-ylsulfanyl)butan-2-yl]carbamate and its pyrimidin-2-yl analogue

Vellasco, Walcimar T.; Gomes, Cláudia R. B.; Vasconcelos, Thatyana R. A.; Wardell, James L.; Otero-de-la-Roza, Alberto; Jotani, Mukesh M.; Tiekink, Edward R. T.

doi:10.1515/zkri-2016-1990

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“…As part of our ongoing structural studies of compounds having biological activities [35][36][37][38], some of us have reported the structures of 2-oxo-2H-chromene-3-carboxamides, 1, see Figure 1 [39,40]. These studies, and a survey of related compounds in the CCDC data base, indicated the near planarity of such molecules arising from the very strong classical intramolecular N-H • • • O hydrogen bond, involving the amido group and the chromene carbonyl oxygen atom, which essentially fixes the overall conformation to be near planar, see Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Crystal structures, Hirsfeld surface analysis and a computational study of four ethyl 2-oxo-2H-chromene-3-carboxylate derivatives: a survey of organyl 2-oxo-2H-chromene-3-carboxylate structures

Gomes

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Mourik

et al. 2019

Zeitschrift Für Kristallographie - Crystalline Materials

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Crystal structures, Hirshfeld surface analysis and a computational study have been carried out on 2-oxo-2H-chromene-3-carboxylates. Crystal structures are reported for ethyl R-2-oxo-2H-chromene-3-carboxylate derivatives, 2a: R=6-Me, 2b: 7-Me, 2c: 7-Me, 2d: R=7-MeO. In contrast to 2-oxo-2H-chromene-3-carboxamides, 1, in which classical intramolecular N–H···O hydrogen bonds stabilize planar structures and hinder rotation of the amido group out of the coumarin plane in 2, without an equivalent hydrogen bond, there is a greater rotational freedom of the carboxylate group. The interplanar angles between the coumarin core and its attached –C(O)–R substituent in crystalline 2a, 2b, 2c and 2d are 10.41(6), 36.65(6), 10.4(2) and 5.64(6)°, respectively, with distances between the carbonyl oxygen atoms of 2.8255(16), 2.9278(16), 4.226(2) and 2.8328(14) Å, respectively. A theoretical study of molecular conformations was carried out at the M06-2X density level with the 6-31+G(d) and aug-cc-pVTZ basis sets, in methanol solution modeled by PCM, indicated that the most stable conformations had the carbonyl group of the ester in the plane of the coumarin core: the s-cis arrangement of the ester carbonyl and the 2-oxo moieties being the slightly more stable than the s-trans form by less than 0.5 kcal/mol. The experimental conformations of 2a and 2d match well the low energy s-cis arrangement, and 2c matches the slightly lesser stable s-trans arrangement found in the theoretical study. A survey of the molecular conformations of more than 50 2H-chromene-3-carboxylates derivatives in the CCDC data base indicated two distinct groupings of conformations, s-cis and s-trans, each with interplanar angles <30°.

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Section: Introductionmentioning

confidence: 99%

Crystal structures, Hirsfeld surface analysis and a computational study of four ethyl 2-oxo-2H-chromene-3-carboxylate derivatives: a survey of organyl 2-oxo-2H-chromene-3-carboxylate structures

Gomes

Low

Mourik

et al. 2019

Zeitschrift Für Kristallographie - Crystalline Materials

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Crystallographic and computational study of t-butyl N-[3-hydroxy-1-phenyl-4-(pyridin- 2-ylsulfanyl)butan-2-yl]carbamate and its pyrimidin-2-yl analogue

Abstract: The crystal structure analysis of the biologically-relevant title compound (

Cited by 1 publication

References 24 publications

Crystal structures, Hirsfeld surface analysis and a computational study of four ethyl 2-oxo-2H-chromene-3-carboxylate derivatives: a survey of organyl 2-oxo-2H-chromene-3-carboxylate structures

Crystal structures, Hirsfeld surface analysis and a computational study of four ethyl 2-oxo-2H-chromene-3-carboxylate derivatives: a survey of organyl 2-oxo-2H-chromene-3-carboxylate structures

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