2-amino-5-nitrothiazole monoethanol solvate: triply-interwoven hydrogenbonded sheets containing centrosymmetric R-2(2)(8) and R-10(10)(38) rings

C Glidewell, J N Low, J M S Skakle, J L Wardell

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Abstract

2-Amino-5-nitrothiazole crystallizes from solution in ethanol as a monosolvate, C3H3N3O2S.C2H6O, in which the thiazole component has a strongly polarized molecular-electronic structure. The thiazole molecules are linked into centrosymmetric dimers by paired N-H...N hydrogen bonds [H...N=2.09 Angstrom, N...N=2.960 (6) Angstrom and N-H...N=169degrees], and these dimers are linked by the ethanol molecules, via a two-centred N-H...O hydrogen bond [H...O=1.98 Angstrom, N...O=2.838 (5) Angstrom and N-H...O=164degrees] and a planar asymmetric three-centred O-H...(O)(2) hydrogen bond [H...O=2.07 and 2.53 Angstrom, O...O=2.900 (5) and 3.188 (5) Angstrom, O-H...O=169 and 136degrees, and O...H...O=55degrees], into sheets built from alternating R-2(2)(8) and R-10(10)(38) rings. These sheets are triply interwoven.

Original languageEnglish
Number of pages4
JournalActa Crystallographica Section C, Crystal Structure Communications
Volume60
DOIs
Publication statusPublished - 2004

Keywords

  • NITROANILINE ANALOGS
  • CRYSTAL

Cite this

@article{c5657cf358c84620bbefb9b977a5ba6e,
title = "2-amino-5-nitrothiazole monoethanol solvate: triply-interwoven hydrogenbonded sheets containing centrosymmetric R-2(2)(8) and R-10(10)(38) rings",
abstract = "2-Amino-5-nitrothiazole crystallizes from solution in ethanol as a monosolvate, C3H3N3O2S.C2H6O, in which the thiazole component has a strongly polarized molecular-electronic structure. The thiazole molecules are linked into centrosymmetric dimers by paired N-H...N hydrogen bonds [H...N=2.09 Angstrom, N...N=2.960 (6) Angstrom and N-H...N=169degrees], and these dimers are linked by the ethanol molecules, via a two-centred N-H...O hydrogen bond [H...O=1.98 Angstrom, N...O=2.838 (5) Angstrom and N-H...O=164degrees] and a planar asymmetric three-centred O-H...(O)(2) hydrogen bond [H...O=2.07 and 2.53 Angstrom, O...O=2.900 (5) and 3.188 (5) Angstrom, O-H...O=169 and 136degrees, and O...H...O=55degrees], into sheets built from alternating R-2(2)(8) and R-10(10)(38) rings. These sheets are triply interwoven.",
keywords = "NITROANILINE ANALOGS, CRYSTAL",
author = "C Glidewell and Low, {J N} and Skakle, {J M S} and Wardell, {J L}",
year = "2004",
doi = "10.1107/S0108270103024533",
language = "English",
volume = "60",
journal = "Acta Crystallographica Section C, Crystal Structure Communications",
issn = "0108-2701",
publisher = "Wiley-Blackwell",

}

TY - JOUR

T1 - 2-amino-5-nitrothiazole monoethanol solvate: triply-interwoven hydrogenbonded sheets containing centrosymmetric R-2(2)(8) and R-10(10)(38) rings

AU - Glidewell, C

AU - Low, J N

AU - Skakle, J M S

AU - Wardell, J L

PY - 2004

Y1 - 2004

N2 - 2-Amino-5-nitrothiazole crystallizes from solution in ethanol as a monosolvate, C3H3N3O2S.C2H6O, in which the thiazole component has a strongly polarized molecular-electronic structure. The thiazole molecules are linked into centrosymmetric dimers by paired N-H...N hydrogen bonds [H...N=2.09 Angstrom, N...N=2.960 (6) Angstrom and N-H...N=169degrees], and these dimers are linked by the ethanol molecules, via a two-centred N-H...O hydrogen bond [H...O=1.98 Angstrom, N...O=2.838 (5) Angstrom and N-H...O=164degrees] and a planar asymmetric three-centred O-H...(O)(2) hydrogen bond [H...O=2.07 and 2.53 Angstrom, O...O=2.900 (5) and 3.188 (5) Angstrom, O-H...O=169 and 136degrees, and O...H...O=55degrees], into sheets built from alternating R-2(2)(8) and R-10(10)(38) rings. These sheets are triply interwoven.

AB - 2-Amino-5-nitrothiazole crystallizes from solution in ethanol as a monosolvate, C3H3N3O2S.C2H6O, in which the thiazole component has a strongly polarized molecular-electronic structure. The thiazole molecules are linked into centrosymmetric dimers by paired N-H...N hydrogen bonds [H...N=2.09 Angstrom, N...N=2.960 (6) Angstrom and N-H...N=169degrees], and these dimers are linked by the ethanol molecules, via a two-centred N-H...O hydrogen bond [H...O=1.98 Angstrom, N...O=2.838 (5) Angstrom and N-H...O=164degrees] and a planar asymmetric three-centred O-H...(O)(2) hydrogen bond [H...O=2.07 and 2.53 Angstrom, O...O=2.900 (5) and 3.188 (5) Angstrom, O-H...O=169 and 136degrees, and O...H...O=55degrees], into sheets built from alternating R-2(2)(8) and R-10(10)(38) rings. These sheets are triply interwoven.

KW - NITROANILINE ANALOGS

KW - CRYSTAL

U2 - 10.1107/S0108270103024533

DO - 10.1107/S0108270103024533

M3 - Article

VL - 60

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

ER -