Abstract
The molecules of ethyl 4-(5-amino-3-methyl-1H-pyrazol-1-yl)benzoate, C13H15N3O2, are linked by two independent N-H...O hydrogen bonds into a chain of edge-fused and alternating R(4)2(8) and R(2)2(20) rings. A combination of N-H...N and N-H...O hydrogen bonds links the molecules of methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate, C15H19N3O2, into sheets of alternating R(2)2(20) and R(6)6(32) rings. In 4-(5-amino-3-methyl-1H-pyrazol-1-yl)benzoic acid monohydrate, C11H11N3O2.H2O, the molecular components are linked into a three-dimensional framework structure by a combination of five independent hydrogen bonds, two of O-H...N type and one each of O-H...O, N-H...O and N-H...N types.
Highlights
A combination of NÐ HÁ Á ÁN and NÐHÁ Á ÁO hydrogen bonds links the molecules of methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate, C15H19N3O2, into sheets of alternating R22(20) and R66(32) rings
In 4-(5-amino-3-methyl-1H-pyrazol-1-yl)benzoic acid monohydrate, C11H11N3O2ÁH2O, the molecular components are linked into a three-dimensional framework structure by a combination of ®ve independent hydrogen bonds, two of OÐ HÁ Á ÁN type and one each of OÐHÁ Á ÁO, NÐHÁ Á ÁO and NÐ HÁ Á ÁN types
As precursors for the synthesis of pyrazolo[1,5-a][1,3,5]benzotriazepines, which are useful as drugs, agrochemicals and dye intermediates (Tachibana & Kaneko, 1989), we have synthesized several 4-(5-aminopyrazol-1-yl)benzoates by construction of the pyrazole ring from 4-hydrazinobenzoic acid and 3-aminocrotononitrile, and report here the structures of three substituted 4-pyrazolylbenzoic acid derivatives, namely ethyl 4-(5-amino-3-methyl-1H-pyrazol-1-yl)benzoate, (I), methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate, (II), and 4-(5-amino-3-methyl-1H-pyrazol-1-yl)benzoic acid monohydrate, (III) (Figs. 1±3)
Summary
The molecules of ethyl 4-(5-amino-3-methyl-1H-pyrazol-1yl)benzoate, C13H15N3O2, are linked by two independent NÐ HÁ Á ÁO hydrogen bonds into a chain of edge-fused and alternating R24(8) and R22(20) rings. A combination of NÐ HÁ Á ÁN and NÐHÁ Á ÁO hydrogen bonds links the molecules of methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate, C15H19N3O2, into sheets of alternating R22(20) and R66(32) rings. Four further hydrogen bonds link the molecular components into a single three-dimensional framework structure, whose formation is readily analysed in terms of three independent one-dimensional substructures, only one of which involves the water molecule. The second substructure runs parallel to the [010] direction and consists of simple chains built from the organic component only; amino atom N45 at (x, y, z) acts as a hydrogen-bond donor, via. MS (70 eV) m/z (%): 273 (53, M+), 258 (100), 231 (83)
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