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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

  • Walcimar T. Vellasco Junior , Claudia R.B. Gomes , Thatyana R.A. Vasconcelos , James L. Wardell EMAIL logo , Alberto Otero-de-la-Roza , Mukesh M. Jotani and Edward R.T. Tiekink EMAIL logo
Published/Copyright: September 27, 2016
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 231 Issue 11

Abstract

The crystal structure analysis of the biologically-relevant title compound (1) shows the carbonyl-O2 and amide-H atoms to be anti, and perpendicular relationships between the carbamate residue and the pyridyl ring [dihedral angle=84.60(10)°] and between the carbamate and aryl ring [74.84(11)°]; the rings are approximately co-planar [12.07(17)°]. An intramolecular hydroxyl-O–H···N(pyridyl) hydrogen bond that closes a S(7) loop is noted. Of interest is the observation that this hydrogen bond is not found in the structure of the pyrimidinyl analogue (2) which was characterised as a monohydrate, i.e. 2·H2O, in an earlier study. Density-functional theory calculations show the observed conformation in 1 is 2.0 kcal/mol more stable than the conformation where the intramolecular hydrogen bond is absent. This energy difference reduces to ca 0.5 kcal/mol in the case of 2. The differences in molecular conformations found for 1 and 2 are therefore ascribed to the dictates of overall molecular packing, in particular due to the influence of lattice water in 2·H2O.

Keywords: conformation; crystal structure analysis; DFT; 2-Hydroxyethylamine cores; X-ray diffraction

Acknowledgments

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW also acknowledges support from CAPES (Brazil). AOR thanks the Spanish Malta/Consolider initiative (no. CSD2007-00045).

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Supplemental Material:

The online version of this article (DOI: 10.1515/zkri-2016-1990) offers supplementary material, available to authorized users.

Received: 2016-7-17
Accepted: 2016-8-23
Published Online: 2016-9-27
Published in Print: 2016-11-1

©2016 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Monoclinic superstructure of Pr3Rh4Ge4
  5. Organic and Metalorganic Crystal Structures
  6. A conformational polymorph of Ph3PAu[SC(OEt)=NPh] featuring an intramolecular Au···π interaction
  7. 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
  8. Mesoscale twinning in shells of Pinctada martensii
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https://doi.org/10.1515/zkri-2016-1990
Keywords for this article
conformation; crystal structure analysis; DFT; 2-Hydroxyethylamine cores; X-ray diffraction

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Monoclinic superstructure of Pr3Rh4Ge4
  5. Organic and Metalorganic Crystal Structures
  6. A conformational polymorph of Ph3PAu[SC(OEt)=NPh] featuring an intramolecular Au···π interaction
  7. 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
  8. Mesoscale twinning in shells of Pinctada martensii
  9. Waters in room temperature and cryo protein crystal structures
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