Hydrogen bonding in C-substituted nitroanilines: n-stacked sheets of R 4 4(20) and R 4 4(28) rings in 2-cyano-4-nitroaniline

C. Glidewell, Janet Mabel Scott Skakle, J. L. Wardell

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

In the title compound, C7H5N3O2, which crystallizes with Z' = 2 in space group P2(1)/c, the two independent molecules both exhibit positional disorder, with refined site-occupancy factors of 0.947 (2) and 0.053 (2) for the major and minor components, respectively. The major components have polarized molecular electronic structures. The two major components are linked into sheets of alternating R-4(4)(20) and R-4(4)(28) rings by two N - H...O hydrogen bonds [H...O = 2.18 and 2.21 Angstrom, N...O = 3.022 (2) and 3.043 (2) Angstrom and N - H...O both 159degrees] and two N - H...N hydrogen bonds [H...N = 2.14 and 2.17 Angstrom, N...N = 2.990 (2) and 3.001 (2) Angstrom, and N - H...N = 162 and 158degrees]. The sheets are linked into a three-dimensional framework by a single aromatic pi-pi stacking interaction.

Original languageEnglish
Pages (from-to)o35-o37
Number of pages3
JournalActa Crystallographica Section C, Crystal Structure Communications
VolumeC60
DOIs
Publication statusPublished - 2004

Keywords

  • CRYSTAL-STRUCTURE

Cite this

@article{49a0cd90210142579291b75dcaff2251,
title = "Hydrogen bonding in C-substituted nitroanilines: n-stacked sheets of R 4 4(20) and R 4 4(28) rings in 2-cyano-4-nitroaniline",
abstract = "In the title compound, C7H5N3O2, which crystallizes with Z' = 2 in space group P2(1)/c, the two independent molecules both exhibit positional disorder, with refined site-occupancy factors of 0.947 (2) and 0.053 (2) for the major and minor components, respectively. The major components have polarized molecular electronic structures. The two major components are linked into sheets of alternating R-4(4)(20) and R-4(4)(28) rings by two N - H...O hydrogen bonds [H...O = 2.18 and 2.21 Angstrom, N...O = 3.022 (2) and 3.043 (2) Angstrom and N - H...O both 159degrees] and two N - H...N hydrogen bonds [H...N = 2.14 and 2.17 Angstrom, N...N = 2.990 (2) and 3.001 (2) Angstrom, and N - H...N = 162 and 158degrees]. The sheets are linked into a three-dimensional framework by a single aromatic pi-pi stacking interaction.",
keywords = "CRYSTAL-STRUCTURE",
author = "C. Glidewell and Skakle, {Janet Mabel Scott} and Wardell, {J. L.}",
year = "2004",
doi = "10.1107/S0108270103027057",
language = "English",
volume = "C60",
pages = "o35--o37",
journal = "Acta Crystallographica Section C, Crystal Structure Communications",
issn = "0108-2701",
publisher = "Wiley-Blackwell",

}

TY - JOUR

T1 - Hydrogen bonding in C-substituted nitroanilines: n-stacked sheets of R 4 4(20) and R 4 4(28) rings in 2-cyano-4-nitroaniline

AU - Glidewell, C.

AU - Skakle, Janet Mabel Scott

AU - Wardell, J. L.

PY - 2004

Y1 - 2004

N2 - In the title compound, C7H5N3O2, which crystallizes with Z' = 2 in space group P2(1)/c, the two independent molecules both exhibit positional disorder, with refined site-occupancy factors of 0.947 (2) and 0.053 (2) for the major and minor components, respectively. The major components have polarized molecular electronic structures. The two major components are linked into sheets of alternating R-4(4)(20) and R-4(4)(28) rings by two N - H...O hydrogen bonds [H...O = 2.18 and 2.21 Angstrom, N...O = 3.022 (2) and 3.043 (2) Angstrom and N - H...O both 159degrees] and two N - H...N hydrogen bonds [H...N = 2.14 and 2.17 Angstrom, N...N = 2.990 (2) and 3.001 (2) Angstrom, and N - H...N = 162 and 158degrees]. The sheets are linked into a three-dimensional framework by a single aromatic pi-pi stacking interaction.

AB - In the title compound, C7H5N3O2, which crystallizes with Z' = 2 in space group P2(1)/c, the two independent molecules both exhibit positional disorder, with refined site-occupancy factors of 0.947 (2) and 0.053 (2) for the major and minor components, respectively. The major components have polarized molecular electronic structures. The two major components are linked into sheets of alternating R-4(4)(20) and R-4(4)(28) rings by two N - H...O hydrogen bonds [H...O = 2.18 and 2.21 Angstrom, N...O = 3.022 (2) and 3.043 (2) Angstrom and N - H...O both 159degrees] and two N - H...N hydrogen bonds [H...N = 2.14 and 2.17 Angstrom, N...N = 2.990 (2) and 3.001 (2) Angstrom, and N - H...N = 162 and 158degrees]. The sheets are linked into a three-dimensional framework by a single aromatic pi-pi stacking interaction.

KW - CRYSTAL-STRUCTURE

U2 - 10.1107/S0108270103027057

DO - 10.1107/S0108270103027057

M3 - Article

VL - C60

SP - o35-o37

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

ER -