Hydrogen-bonded chains of rings in methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate and hydrogen-bonded sheets in methyl 1-(5-methyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate

J. Portilla, E. G. Mata, M. Nogueras, J. Cobo, John N. Low, C. Glidewell

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Molecules of methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate, C12H12N4O4, (I), exhibit a polarized (charge-separated) structure in the nitroaniline portion. The molecules are linked into chains of edge-fused R-2(2)(16) and R22( 22) rings by a combination of N-H center dot center dot center dot O(carbonyl) and C-H center dot center dot center dot O(nitro) hydrogen bonds. Methyl 1-(5-methyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate, C13H12N4O2, (II), which is readily formed from (I) by reduction followed by ring formation, crystallizes with Z' = 2 in the space group P1. Each of the two independent molecular types is linked into sheets of R-4(4)(28) rings by a combination of N-H center dot center dot center dot N and C-H center dot center dot center dot O(carbonyl) hydrogen bonds.

Original languageEnglish
Pages (from-to)O38-O41
Number of pages4
JournalActa Crystallographica Section C, Crystal Structure Communications
VolumeC63
DOIs
Publication statusPublished - 2007

Keywords

  • X-ray
  • diffraction

Cite this

@article{080154db3cad4ab6b915837ff60fa7e6,
title = "Hydrogen-bonded chains of rings in methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate and hydrogen-bonded sheets in methyl 1-(5-methyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate",
abstract = "Molecules of methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate, C12H12N4O4, (I), exhibit a polarized (charge-separated) structure in the nitroaniline portion. The molecules are linked into chains of edge-fused R-2(2)(16) and R22( 22) rings by a combination of N-H center dot center dot center dot O(carbonyl) and C-H center dot center dot center dot O(nitro) hydrogen bonds. Methyl 1-(5-methyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate, C13H12N4O2, (II), which is readily formed from (I) by reduction followed by ring formation, crystallizes with Z' = 2 in the space group P1. Each of the two independent molecular types is linked into sheets of R-4(4)(28) rings by a combination of N-H center dot center dot center dot N and C-H center dot center dot center dot O(carbonyl) hydrogen bonds.",
keywords = "X-ray, diffraction",
author = "J. Portilla and Mata, {E. G.} and M. Nogueras and J. Cobo and Low, {John N.} and C. Glidewell",
year = "2007",
doi = "10.1107/S0108270106044611",
language = "English",
volume = "C63",
pages = "O38--O41",
journal = "Acta Crystallographica Section C, Crystal Structure Communications",
issn = "0108-2701",
publisher = "Wiley-Blackwell",

}

TY - JOUR

T1 - Hydrogen-bonded chains of rings in methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate and hydrogen-bonded sheets in methyl 1-(5-methyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate

AU - Portilla, J.

AU - Mata, E. G.

AU - Nogueras, M.

AU - Cobo, J.

AU - Low, John N.

AU - Glidewell, C.

PY - 2007

Y1 - 2007

N2 - Molecules of methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate, C12H12N4O4, (I), exhibit a polarized (charge-separated) structure in the nitroaniline portion. The molecules are linked into chains of edge-fused R-2(2)(16) and R22( 22) rings by a combination of N-H center dot center dot center dot O(carbonyl) and C-H center dot center dot center dot O(nitro) hydrogen bonds. Methyl 1-(5-methyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate, C13H12N4O2, (II), which is readily formed from (I) by reduction followed by ring formation, crystallizes with Z' = 2 in the space group P1. Each of the two independent molecular types is linked into sheets of R-4(4)(28) rings by a combination of N-H center dot center dot center dot N and C-H center dot center dot center dot O(carbonyl) hydrogen bonds.

AB - Molecules of methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate, C12H12N4O4, (I), exhibit a polarized (charge-separated) structure in the nitroaniline portion. The molecules are linked into chains of edge-fused R-2(2)(16) and R22( 22) rings by a combination of N-H center dot center dot center dot O(carbonyl) and C-H center dot center dot center dot O(nitro) hydrogen bonds. Methyl 1-(5-methyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate, C13H12N4O2, (II), which is readily formed from (I) by reduction followed by ring formation, crystallizes with Z' = 2 in the space group P1. Each of the two independent molecular types is linked into sheets of R-4(4)(28) rings by a combination of N-H center dot center dot center dot N and C-H center dot center dot center dot O(carbonyl) hydrogen bonds.

KW - X-ray

KW - diffraction

U2 - 10.1107/S0108270106044611

DO - 10.1107/S0108270106044611

M3 - Article

VL - C63

SP - O38-O41

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

ER -