Navegar

Colección

Datos Estadísticas

Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

An unpredicted fourfold screw N—H.O hydrogen bond C(4) motif in a primary dicarboxamide (trans-cyclo­hexane-1,4-dicarboxamide, C8H14N2O2) was investigated by single-crystal X-ray diffraction and IR and Raman spectroscopies. Electron-density topology and inter­molecular energy analyses determined from ab initio calculations were employed to examine the influence of weak C—H.O hydrogen-bond inter­actions on the peculiar arrangement of mol­ecules in the tetra­gonal P43212 space group. In addition, the way in which the co-operative effects of those weak bonds might modify their relative influence on mol­ecular packing was estimated from cluster calculations. Based on the results, a structural model is proposed which helps to rationalize the unusual fourfold screw mol­ecular arrangement. © 2018 International Union of Crystallography.

Registro:

Documento: Artículo
Título:Role of weak C—H…O and strong N—H…O inter­molecular inter­actions on the high-symmetry mol­ecular packing of trans-cyclo­hexane-1,4-dicarboxamide
Autor:Garcí-Reyes, F.; Fantoni, A.C.; Barón, M.; Romano, R.M.; Punte, G.M.; Echeverrí, G.A.
Filiación:IFLP (CONICET, CCT–La Plata), Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 115 y 49, La Plata, 1900, Argentina
Facultad de Ciencias Exactas y Naturales, Universidad de Belgrano, Villanueva 1324, Buenos Aires, 1426, Argentina
CEQUINOR (UNLP–CONICET, CCT–La Plata), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata, 1900, Argentina
Facultad de Ingeniería, Universidad Nacional de La Plata, 115 y 49, La Plata, 1900, Argentina
Palabras clave:Ab initio calculations; Carboxamide; Crystal structure; Hydrogen bonds; IR spectroscopy; Raman spectroscopy; Calculations; Crystal structure; Hexane; Infrared spectroscopy; Raman spectroscopy; Screws; Single crystals; Cyclohexane; Ab initio calculations; Carboxamides; Cluster calculations; Co-operative effects; Electron-density topology; IR and Raman spectroscopy; Single crystal x-ray diffraction; Structural modeling; Hydrogen bond interaction; Intermolecular interactions; Molecular arrangements; Hydrogen bonds
Año:2018
Volumen:74
Número:10
Página de inicio:1068
Página de fin:1078
DOI: http://dx.doi.org/10.1107/S2053229618011750
Título revista:Acta Crystallographica Section C: Structural Chemistry
Título revista abreviado:Acta crystallogr., C Struct. Chem.
ISSN:20532296
CODEN:ACSCG
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20532296_v74_n10_p1068_GarciReyes

Referencias:

  • (2014) Crysalis PRO, , Agilent Technologies Ltd, Yarnton, Oxfordshire, England
  • Bader, R.F.W., (1990) In Atoms in Molecules: A Quantum Theory, , Oxford: Clarendon Press and Oxford Science Publications
  • Barón, M., de Zenobi, E.L., Davidson, M., (1975) J. Mol. Struct, 24, pp. 432-438
  • Berkovitch-Yellin, Z., Leiserowitz, L., (1980) J. Am. Chem. Soc, 102, pp. 7677-7690
  • Biegler-König, F., Schönbohm, J., (2002) J. Comput. Chem, 23, pp. 1489-1494
  • Boys, S.F., Bernardi, F., (1970) Mol. Phys, 19, pp. 553-566
  • Cobbledick, R.E., Small, R.W.H., (1972) Acta Cryst, B28, pp. 2893-2896
  • Desiraju, G.R., (1995) Angew. Chem. Int. Ed. Engl, 34, pp. 2311-2327
  • Dovesi, R., Orlando, R., Erba, A., Zicovich-Wilson, C.M., Civalleri, B., Casassa, S., Maschio, L., Kirtman, B., (2014) Int. J. Quantum Chem, 114, pp. 1287-1317
  • Echeverría, G.A., Barón, M., Punte, G.M., (2000) Struct. Chem, 11, pp. 35-40
  • Echeverría, G.A., Goeta, A., Barón, M., Punte, G.M., (2003) Acta Cryst, E59, pp. o959-o961
  • Echeverría, G.A., Punte, G.M., Rivero, B.E., Barón, M., (1995) Acta Cryst, C51, pp. 1020-1023
  • Echeverría, G.A., Punte, G.M., Rivero, B.E., Barón, M., (1995) Acta Cryst, C51, pp. 1023-1026
  • Farrugia, L.J., (1997) J. Appl. Cryst, 30, p. 565
  • Farrugia, L.J., (2012) J. Appl. Cryst, 45, pp. 849-854
  • Frisch, M.J., (2004) GAUSSIAN03, , http://www.gaussian.com, Gaussian Inc., Wallingford, CT, USA
  • Gatti, C., Casassa, S., (2014) TOPOND14 User’s Manual, , http://www.crystal.unito.it/topond/topond.pdf, CNR-ISTM Milano, Milano, Italy
  • Gatti, C., Saunders, V.R., Roetti, C., (1994) J. Chem. Phys, 101, pp. 10686-10696
  • Gilli, G., Bellucci, F., Ferretti, V., Bertolasi, V., (1989) J. Am. Chem. Soc, 111, pp. 1023-1028
  • Groom, C.R., Bruno, I.J., Lightfoot, M.P., Ward, S.C., (2016) Acta Cryst, B72, pp. 171-179
  • Hongwei, T., Wenwen, Q., Guangju, C., Ruozhuang, L., (2005) J. Phys. Chem. A, 109, pp. 6303-6308
  • Jensen, F., (2007) In Introduction to Computational Chemistry, , 2nd ed. London: John Wiley & Sons Ltd
  • Kuduva, S.S., Bläser, D., Boese, R., Desiraju, G.R., (2001) J. Org. Chem, 66, pp. 1621-1626
  • Leiserowitz, L., (1976) Acta Cryst, B32, pp. 775-802
  • Leiserowitz, L., Hagler, A.T., (1983) Proc. R. Soc. London Ser. A, 388, pp. 133-175
  • Leiserowitz, L., Schmidt, G.M.J., (1969) J. Chem. Soc. A, pp. 2372-2382
  • Lin-Vien, D., Colthup, N.B., Fateley, W.G., Grasselli, J.G., (1991) In the Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, , London: Academic Press Ltd
  • Macrae, C.F., Bruno, I.J., Chisholm, J.A., Edgington, P.R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Wood, P.A., (2008) J. Appl. Cryst, 41, pp. 466-470
  • Nardelli, M., (1995) J. Appl. Cryst, 28, p. 659
  • Parsons, S., Flack, H.D., Wagner, T., (2013) Acta Cryst, B69, pp. 249-259
  • Reed, A.E., Weinhold, F., (1986) J. Chem. Phys, 84, pp. 5687-5705
  • Scott, A.P., Radom, L., (1996) J. Phys. Chem, 100, pp. 16502-16513
  • Sheldrick, G.M., (2015) Acta Cryst, A71, pp. 3-8
  • Sheldrick, G.M., (2015) Acta Cryst, C71, pp. 3-8
  • Simon, S., Duran, M., Dannenberg, J.J., (1996) J. Chem. Phys, 105, pp. 11024-11031
  • Spek, A.L., (2009) Acta Cryst, D65, pp. 148-155
  • Takamizawa, S., Miyamoto, Y., (2014) Angew. Chem. Int. Ed, 53, pp. 6970-6973
  • van Derwaals, J.D., (1873), Doctoral Dissertation, Leiden University, The Netherlands; Zipp, C.F., Fernandes, M.A., Michael, J.P., Winks, S., (2009) Acta Cryst, C65, pp. o553-o554

Citas:

---------- APA ----------
Garcí-Reyes, F., Fantoni, A.C., Barón, M., Romano, R.M., Punte, G.M. & Echeverrí, G.A. (2018) . Role of weak C—H…O and strong N—H…O inter­molecular inter­actions on the high-symmetry mol­ecular packing of trans-cyclo­hexane-1,4-dicarboxamide. Acta Crystallographica Section C: Structural Chemistry, 74(10), 1068-1078.
http://dx.doi.org/10.1107/S2053229618011750
---------- CHICAGO ----------
Garcí-Reyes, F., Fantoni, A.C., Barón, M., Romano, R.M., Punte, G.M., Echeverrí, G.A. "Role of weak C—H…O and strong N—H…O inter­molecular inter­actions on the high-symmetry mol­ecular packing of trans-cyclo­hexane-1,4-dicarboxamide" . Acta Crystallographica Section C: Structural Chemistry 74, no. 10 (2018) : 1068-1078.
http://dx.doi.org/10.1107/S2053229618011750
---------- MLA ----------
Garcí-Reyes, F., Fantoni, A.C., Barón, M., Romano, R.M., Punte, G.M., Echeverrí, G.A. "Role of weak C—H…O and strong N—H…O inter­molecular inter­actions on the high-symmetry mol­ecular packing of trans-cyclo­hexane-1,4-dicarboxamide" . Acta Crystallographica Section C: Structural Chemistry, vol. 74, no. 10, 2018, pp. 1068-1078.
http://dx.doi.org/10.1107/S2053229618011750
---------- VANCOUVER ----------
Garcí-Reyes, F., Fantoni, A.C., Barón, M., Romano, R.M., Punte, G.M., Echeverrí, G.A. Role of weak C—H…O and strong N—H…O inter­molecular inter­actions on the high-symmetry mol­ecular packing of trans-cyclo­hexane-1,4-dicarboxamide. Acta crystallogr., C Struct. Chem. 2018;74(10):1068-1078.
http://dx.doi.org/10.1107/S2053229618011750