Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 7 (July 2013)

organic compounds

sf3196 scheme

Acta Cryst. (2013). C69, 754-760    [ doi:10.1107/S0108270113013590 ]

Four related esters: two 4-(aroylhydrazinyl)-3-nitrobenzoates and two 3-aryl-1,2,4-benzotriazine-6-carboxylates

E. Cortés, R. Abonía, J. Cobo and C. Glidewell

Abstract: The molecules of both methyl 4-[2-(4-chlorobenzoyl)hydrazinyl]-3-nitrobenzoate, C15H12ClN3O5, (I), and methyl 4-[2-(2-fluorobenzoyl)hydrazinyl]-3-nitrobenzoate, C15H12FN3O5, (II), contain an intramolecular N-H...O hydrogen bond, and both show electronic polarization in the nitrated aryl ring. In both compounds, molecules are linked by a combination of N-H...O and C-H...O hydrogen bonds to form sheets, which are built from R43(18) rings in (I) and from R44(28) rings in (II). In each of methyl 3-phenyl-1,2,4-benzotriazine-6-carboxylate, C15H11N3O2, (III), and methyl 3-(4-methylphenyl)-1,2,4-benzotriazine-6-carboxylate, C16H13N3O2, (IV), the benzotriazine unit shows naphthalene-type delocalization. There are no hydrogen bonds in the structures of compounds (III) and (IV), but in both compounds, the molecules are linked into chains by [pi]-[pi] stacking interactions involving the benzotriazine units. The mechanism of chain formation is the same in both (III) and (IV), and the different orientations of the two chains can be related to the approximate relationship between the unit-cell metrics for (III) and (IV).

Formula: C15H12ClN3O5, C15H12FN3O5, C15H11N3O2 and C16H13N3O2

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Structure factor file (CIF format) (161.8 kbytes)
[ doi:10.1107/S0108270113013590/sf3196Isup2.hkl ]
Contains datablock I

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Structure factor file (CIF format) (167.6 kbytes)
[ doi:10.1107/S0108270113013590/sf3196IIsup3.hkl ]
Contains datablock II

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Structure factor file (CIF format) (131.4 kbytes)
[ doi:10.1107/S0108270113013590/sf3196IIIsup4.hkl ]
Contains datablock III

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Structure factor file (CIF format) (149.8 kbytes)
[ doi:10.1107/S0108270113013590/sf3196IVsup5.hkl ]
Contains datablock IV


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