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

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.



H-bonding; Oximes; 1,3-Diphenyl-propan-2-one oxime; X-ray diffraction; Crystal structure

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[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.



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