Startseite 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
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

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 und Edward R.T. Tiekink EMAIL logo
Veröffentlicht/Copyright: 27. September 2016
Veröffentlichen auch Sie bei De Gruyter Brill
Manuskript einreichen Informationen für Autor*innen
Zeitschrift für Kristallographie - Crystalline Materials
Aus der Zeitschrift Zeitschrift für Kristallographie - Crystalline Materials Band 231 Heft 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).

References

[1] A. Brik, C.-H. Wong, Org. Biomol. Chem.2003, 1, 5.10.1039/b208248aSuche in Google Scholar PubMed

[2] A. K. Ghosh, G. Bilcer, G. Schiltz, Synthesis2001, 2203.10.1055/s-2001-18434Suche in Google Scholar PubMed PubMed Central

[3] L. R. Marcin, M. A. Higgins, F. C. Zusi, Y. Zhang, M. F. Dee, M. F. Parker, J. K. Muckelbauer, D. M. Camac, P. E. Morin, V. Ramamurthy, A. J. Tebben, K. A. Lentz, J.E. Grace, J. A. Marcinkeviciene, L. M. Kopcho, C. R. Burton, D. M. Barten, J. H. Toyn, J. E. Meredith, C. F. Albright, J. J. Bronson, J. E. Macor, L. A. Thompson, Bioorg. Med. Chem.Lett.2011, 21, 537.10.1016/j.bmcl.2010.10.079Suche in Google Scholar PubMed

[4] W. Cunico, M. L. G. Ferreira, T. G. Ferreira, C. Penido, M. G. M. O. Henriques, L. G. Krettli, F. P. Varotti, A. U. Krettli, Lett. Drug Des. Discov.2008, 5, 178.10.2174/157018008784083938Suche in Google Scholar

[5] W. Cunico, C. R. B. Gomes, M. Moreth, D. P. Manhanini, I. H. Figueiredo, C. Penido, M. G. M. O. Henriques, F. P. Varotti, A. U. Krettli, Eur. J. Med. Chem.2009, 44, 1363.10.1016/j.ejmech.2008.04.009Suche in Google Scholar PubMed

[6] W. Cunico, C. R. B. Gomes, V. Facchinetti, M. Moreth, C. Penido, M. G. M. O. Henriques, F. P. Varotti, L. G. Krettli, A. U. Krettli, F. S. da Silva, E. R. Caffarena, C. S. de Magalhães, Eur. J. Med. Chem.2009, 44, 3816.10.1016/j.ejmech.2009.03.041Suche in Google Scholar PubMed

[7] W. Cunico, C. R. B. Gomes, M. L. G. Ferreira, T. G. Ferreira, D. Cardinot, M. V. N. de Souza, M. C. S. Lourenço, Eur. J. Med. Chem.2011, 46, 974.10.1016/j.ejmech.2011.01.004Suche in Google Scholar PubMed

[8] W. T. Vellasco Junior, G. P. Guedes, T. R. A. Vasconcelos, M. G. F. Vaz,; M. V. N. Souza, A. U. Krettli, L. G. Krettli, A. C. C. Aguiar, C. R. B. Gomes, W. Cunico, Eur. J. Med. Chem.2011, 46, 5688.10.1016/j.ejmech.2011.09.025Suche in Google Scholar PubMed

[9] N. Trudel, R. Garg, N. Messier, S. Sundar, M. Ouellette, M. J. Tremblay. J.Infect. Dis.2008, 198, 1292.10.1086/592280Suche in Google Scholar PubMed

[10] C. R. B. Gomes, T. R. A. Vasconcelos, W. T. Vellasco Junior, J. L.Wardell, S. M. S. V. Wardell, and E. R. T. Tiekink, Acta Cryst.E2011, 67, o2313.10.1107/S1600536811031850Suche in Google Scholar PubMed PubMed Central

[11] C. R. B. Gomes, T. R. A. Vasconcelos, W. T. Vellasco Junior, W. Cunico, J. L. Wardell, S. M. S. V. Wardell, E. R. T. Tiekink, Acta Cryst.E2011, 67, o2447.10.1107/S1600536811033575Suche in Google Scholar

[12] CrystalClear-SM Expert. User Manual. Rigaku/MSC Inc., Rigaku Corporation, The Woodlands, TX, 2011.Suche in Google Scholar

[13] G. M. Sheldrick, Acta Crystallogr. A2008, 64, 112.10.1107/S0108767307043930Suche in Google Scholar

[14] G. M. Sheldrick, Acta Crystallogr. C2015, 71, 3.10.1107/S2053229614024218Suche in Google Scholar

[15] L. J. Farrugia, J. Appl. Crystallogr. 2012, 45, 849.10.1107/S0021889812029111Suche in Google Scholar

[16] A. L. Spek, Acta Crystallogr. D2009, 65, 148.10.1107/S090744490804362XSuche in Google Scholar

[17] J. Gans, D. Shalloway, J. Mol. Graph. Model. 2001, 19, 557.10.1016/S1093-3263(01)00090-0Suche in Google Scholar

[18] DIAMOND, Visual Crystal Structure Information System, Version 3.1, CRYSTAL IMPACT, Postfach 1251, D-53002, 2006.Suche in Google Scholar

[19] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford, CT, USA, 2009.Suche in Google Scholar

[20] O. A. Vydrov, G. E. Scuseria, J. Chem. Phys. 2006, 125, 234109.10.1063/1.2409292Suche in Google Scholar PubMed

[21] O. A. Vydrov, J. Heyd, A. V. Krukau, G. E. Scuseria, J. Chem. Phys. 2006, 125, 074106.10.1063/1.2244560Suche in Google Scholar PubMed

[22] A. D. Becke, E. R. Johnson, J. Chem. Phys. 2007, 127, 154108.10.1063/1.2795701Suche in Google Scholar PubMed

[23] A. Otero-de-la-Roza, E. R. Johnson, J. Chem. Phys. 2013, 138, 204109.10.1063/1.4807330Suche in Google Scholar PubMed

[24] Freely available from https://github.com/aoterodelaroza/postg.Suche in Google Scholar

[25] S. K. Wolff, D. J. Grimwood, J. J. McKinnon, M. J. Turner, D. Jayatilaka, M. A. Spackman, Crystal Explorer (Version 3.1), University of Western Australia, 2012.Suche in Google Scholar

[26] M. A. Spackman, J. J. McKinnon, D. Jayatilaka, CrystEngComm2008, 10, 377.Suche in Google Scholar

[27] D. Jayatilaka, D. J. Grimwood, A. Lee, A. Lemay, A. J. Russel, C. Taylor, S. K. Wolff, C. Chenai, A. Whitton, TONTO – A System for Computational Chemistry, 2005. Available at: http://hirshfeldsurface.net/.Suche in Google Scholar

[28] J. J. McKinnon, M. A. Spackman, A. S. Mitchell, Acta Crystallogr. B2004, 60, 627.10.1107/S0108768104020300Suche in Google Scholar PubMed

[29] J. J. McKinnon, D. Jayatilaka, M. A. Spackman, Chem Commun. 2007, 3814.10.1039/b704980cSuche in Google Scholar PubMed

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

Artikel in diesem Heft

  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
https://doi.org/10.1515/zkri-2016-1990
Schlagwörter für diesen Artikel
conformation; crystal structure analysis; DFT; 2-Hydroxyethylamine cores; X-ray diffraction

Artikel in diesem Heft

  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
Jetzt anmelden und 20% sparen
Institutioneller Zugang
Wie funktioniert Authentifizierung?
Haben Sie eine Idee, wie wir unsere Website verbessern können?
Bitte schreiben Sie uns.
© 2025 De Gruyter Brill
Heruntergeladen am 3.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/zkri-2016-1990/html?lang=de
Button zum nach oben scrollen