Acta Crystallographica Section C

Crystal Structure Communications

Volume 60, Part 1 (January 2004)

Acta Cryst. (2004). C60, o28-o32    [doi:10.1107/S0108270103025435]

Three N²-benzoyloxybenzamidines: sheet structures built from hard and soft hydrogen bonds and aromatic - stacking interactions

C. E. M. Carvalho, S. M. S. V. Wardell, J. L. Wardell, J. M. S. Skakle, J. N. Low and C. Glidewell

Abstract: Molecules of the title compounds N²-(benzoyloxy)benzamidine, C₁₄H₁₂N₂O₂, (I), N²-(2-hydroxybenzoyloxy)benzamidine, C₁₄H₁₂N₂O₃, (II), and N²-benzoyloxy-2-hydroxybenzamidine, C₁₄H₁₂N₂O₃, (III), all have extended chain conformations, with the aryl groups remote from one another. In (I), the molecules are linked into chains by a single N-HN hydrogen bond [HN  =  2.15  Å, NN  =  3.029  (2)  Å and N-HN  =  153°] and these chains are linked into sheets by means of aromatic - stacking interactions. There is one intramolecular O-HO hydrogen bond in (II), and a combination of one three-centre N-H(N,O) hydrogen bond [HN  =  2.46  Å, HO  =  2.31  Å, NN  =  3.190  (2)  Å, NO  =  3.146  (2)  Å, N-HN  =  138° and N-HO  =  154°] and one two-centre C-HO hydrogen bond [HO  =  2.46  Å, CO  = 3.405  (2)  Å and C-HO  =  173°] links the molecules into sheets. In (III), an intramolecular O-HN hydrogen bond and two N-HO hydrogen bonds [HO  =  2.26 and 2.10  Å, NO  =  2.975  (2) and 2.954  (2)  Å, and N-HO  = 138 and 163°] link the molecules into sheets.

Formula: C₁₄H₁₂N₂O₂, C₁₄H₁₂N₂O₃ and C₁₄H₁₂N₂O₃

Online 6 December 2003

	Structure factor file (CIF format) (128.4 kbytes) Contains datablock I
	Structure factor file (CIF format) (135.5 kbytes) Contains datablock II
	Structure factor file (CIF format) (125.2 kbytes) Contains datablock III

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