European Journal of Chemistry

The supramolecular structures of oximes: an update and the crystal structure of 1,3-diphenyl-propan-2-one oxime

Main Article Content

John Nicolson Low
Luís M. N. B. F. Santos
Carlos F. R. A. C. Lima
Paula Brandão
Lígia R. Gomes


The crystal structure of 1,3-diphenyl-propan-2-one oxime, C15H15NO, is described. The compound crystallises in the monoclinic space group C2/c. Centrosymmetrically related molecules are linked to form R22 (6) dimers. An update, since 2003, of a systematic analysis of the hydrogen bonding patterns in oxime structures with and without competitive O-H...A type acceptors (an acceptor other than the nitrogen of the oxime) functional group is made, taking into account their moieties. The majority of these oximes form dimeric, R22 (6), structures but R33 (8) and R44 (12) were also found. C3 chains which were classically claimed as the usual oxime H-bond pattern were rarely observed. They are mostly found in aldoxime structures.


icon graph This Abstract was viewed 6862 times | icon graph Article PDF downloaded 806 times icon graph Article SUPPLEMENTARY FILE downloaded 0 times

How to Cite
Low, J. N.; Santos, L. M. N. B. F.; Lima, C. F. R. A. C.; Brandão, P.; Gomes, L. R. The Supramolecular Structures of Oximes: An Update and the Crystal Structure of 1,3-Diphenyl-Propan-2-One Oxime. Eur. J. Chem. 2010, 1, 61-66.

Article Details

Author Biography

John Nicolson Low, Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland.

Honorary Research Fellow

Department of Chemistry

University of Aberdeen




Crossref - Scopus - Google - European PMC

[1]. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.

[2]. Bertalosi, V.; Gilli G. V. Acta Cryst. 1982, B38, 502-511.

[3]. Bruton, E. A.; Brammer, L.; Pigge, F. C.; Aakeröy, C. B.; Leinen, D. S. New J. Chem. 2003, 27, 1084-1094.

[4]. Marsman, A. W.; Leusink, E. D.; Zwikker, J. W.; Jenneskens, L. W.; Smeets, W. J. J.; Veldman N.; Spek, A.L. Chem. Mater. 1999, 11, 1484-1491.

[5]. Luckhaus D. J. Chem. Phys. 1997, 106, 8409-8426.

[6]. Bruker-Nonius, COLLECT. Bruker-Nonius BV, Delft, The Netherlands, 2004.

[7]. Duisenberg, A. J. M.; Hooft; R. W. W.; Schreurs, A. M. M.; Kroon, J. J. Appl. Cryst. 2000, 33, 893-898.

[8]. Duisenberg, A. J. M.; Kroon-Batenburg, L. M. J.; Schreurs, A. M. M.; J. Appl. Cryst. 2003, 36, 220-229.

[9]. Sheldrick, G. M. SADABS - Bruker Nonius area detector scaling and absorption correction-V2.10, 2003.

[10]. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J. Appl. Cryst. 2005, 38, 381–388.

[11]. Farrugia, L. J. J. Appl. Cryst. 1999, 32, 837–838.

[12]. McArdle, P., OSCAIL for Windows, Version 10, Crystallography Centre, Chemistry Department, NUI Galway, Ireland, 2003.

[13]. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

[14]. Johnson, C. K., ORTEP - A Fortran Thermal Ellipsoid Plot Program, Technical Report ORNL-5138, Oak Ridge National Laboratory, U.S.A., 1967.

[15]. Spek, A. L. (2009). Acta Cryst. D65, 148-155.
PMid:19171970    PMCid:2631630

[16]. Allen, F. H.; Kennard, O.;Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc. Perkin Trans. 1987, 2, S1–19.

[17]. Bernstein, J.; Davis, R. E.; Shimoni, I.; Chang, N.-L. Agnew. Chem. Int. Ed. Engl. 1995, 34, 1555–1573.

[18]. Allen, F. H., Acta Cryst. 2002, B58, 380-388.

[19]. Olmstead, M. M.; Sahbari, J. J. Acta Cryst. 2003, C59, o719–720.

[20]. Kedziorek M.; Hafner, K.; Lindner, H. J. Acta Cryst. 2003, E60, o657–o658.

[21]. Clive, D. L. J.; Pham, M. P.; Subedi, R. J. Am. Chem. Soc. 2007, 129, 2713–2719.

[22]. Lutz, M.; Spek, A. L.; Dabirian, R.; van Walree, C.A.; Jenneskens, L. W. Acta Cryst. 2004, C60, 127–129.

[23]. Parsons, S.; Pu, W.; Ramage, R.; Wood, P. Private Communication to CSD: ACEXM01, 2004.

[24]. Nyui, T.; Nogami, T.; Ishida T. Cryst. Eng. Comm. 2005, 7, 612-615.

[25]. Wang, X. Z.; Jia, J.; Zhang, Y.; Wang, J-W. Acta Cryst. 2006, E62, o2086-o2087.

[26]. Albrecht, M.; Zielke, P.; Rice, C. A.; Suhm M. A. J. Mol. Struc., 2008, 880, 2-13.

Most read articles by the same author(s)

Most read articles by the same author(s)


Dimensions - Altmetric - scite_ - PlumX

Downloads and views


Download data is not yet available.


Metrics Loading ...
License Terms

License Terms


Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License ( By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License ( are administered by Atlanta Publishing House LLC (European Journal of Chemistry).