Solid-State Structure of a Layered Hydrogen-Bonded Salt: Guanidinium 5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonate Methanol Solvate

Victoria A. Russell, Michael Ward

Research output: Contribution to journalArticle

Abstract

Guanidinium 5-benzoyl-4-hydroxy-2-methoxybenzene-sulfonate methanol solvate [C(NH2)3+.(C14H11O 3)SO3-.-CH3OH] crystallizes into a layered structure containing a two-dimensional hydrogen-bonded network typical of guanidinium alkane- and arenesulfonates. All six guanidinium protons and six sulfonate oxygen lone-pair acceptors participate in hydrogen bonding to form nearly planar pseudohexagonal hydrogen-bonded sheets, which can be viewed as parallel connected hydrogen-bonded ribbons. The 5-benzoyl-4-hydroxy-2-methoxybenzene groups are oriented to the same side of each ribbon, but the orientation of these groups on adjacent ribbons alternates with respect to the hydrogen-bonded sheet. The planar sheets stack with interdigitation of the arene groups, resulting in a structure in which layers of 5-benzoyl-4-hydroxy-2-methoxybenzene groups are separated by ionic hydrogen-bonded sheets. Each methanol molecule forms a hydrogen bond to one of the sulfonate O atoms, resulting in this oxygen forming a total of three hydrogen bonds, and fills void volume between the interdigitated 5-benzoyl-4-hydroxy-2-methoxybenzene groups of neighboring sheets. The benzophenone hydroxyl proton forms an intramolecular hydrogen bond to the carbonyl oxygen.

Original languageEnglish (US)
Pages (from-to)209-214
Number of pages6
JournalActa Crystallographica Section B: Structural Science
Volume52
Issue number1
StatePublished - Feb 1 1996

Fingerprint

Guanidine
Methanol
Hydrogen
methyl alcohol
Salts
salts
solid state
Hydrogen bonds
hydrogen
sulfonates
ribbons
Oxygen
Protons
hydrogen bonds
oxygen
Alkanes
protons
Hydroxyl Radical
alkanes
voids

ASJC Scopus subject areas

  • Structural Biology
  • Condensed Matter Physics

Cite this

@article{468cf94190e4482a88142279fd24a36c,
title = "Solid-State Structure of a Layered Hydrogen-Bonded Salt: Guanidinium 5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonate Methanol Solvate",
abstract = "Guanidinium 5-benzoyl-4-hydroxy-2-methoxybenzene-sulfonate methanol solvate [C(NH2)3+.(C14H11O 3)SO3-.-CH3OH] crystallizes into a layered structure containing a two-dimensional hydrogen-bonded network typical of guanidinium alkane- and arenesulfonates. All six guanidinium protons and six sulfonate oxygen lone-pair acceptors participate in hydrogen bonding to form nearly planar pseudohexagonal hydrogen-bonded sheets, which can be viewed as parallel connected hydrogen-bonded ribbons. The 5-benzoyl-4-hydroxy-2-methoxybenzene groups are oriented to the same side of each ribbon, but the orientation of these groups on adjacent ribbons alternates with respect to the hydrogen-bonded sheet. The planar sheets stack with interdigitation of the arene groups, resulting in a structure in which layers of 5-benzoyl-4-hydroxy-2-methoxybenzene groups are separated by ionic hydrogen-bonded sheets. Each methanol molecule forms a hydrogen bond to one of the sulfonate O atoms, resulting in this oxygen forming a total of three hydrogen bonds, and fills void volume between the interdigitated 5-benzoyl-4-hydroxy-2-methoxybenzene groups of neighboring sheets. The benzophenone hydroxyl proton forms an intramolecular hydrogen bond to the carbonyl oxygen.",
author = "Russell, {Victoria A.} and Michael Ward",
year = "1996",
month = "2",
day = "1",
language = "English (US)",
volume = "52",
pages = "209--214",
journal = "Acta Crystallographica Section B: Structural Science",
issn = "0108-7681",
publisher = "International Union of Crystallography",
number = "1",

}

TY - JOUR

T1 - Solid-State Structure of a Layered Hydrogen-Bonded Salt

T2 - Guanidinium 5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonate Methanol Solvate

AU - Russell, Victoria A.

AU - Ward, Michael

PY - 1996/2/1

Y1 - 1996/2/1

N2 - Guanidinium 5-benzoyl-4-hydroxy-2-methoxybenzene-sulfonate methanol solvate [C(NH2)3+.(C14H11O 3)SO3-.-CH3OH] crystallizes into a layered structure containing a two-dimensional hydrogen-bonded network typical of guanidinium alkane- and arenesulfonates. All six guanidinium protons and six sulfonate oxygen lone-pair acceptors participate in hydrogen bonding to form nearly planar pseudohexagonal hydrogen-bonded sheets, which can be viewed as parallel connected hydrogen-bonded ribbons. The 5-benzoyl-4-hydroxy-2-methoxybenzene groups are oriented to the same side of each ribbon, but the orientation of these groups on adjacent ribbons alternates with respect to the hydrogen-bonded sheet. The planar sheets stack with interdigitation of the arene groups, resulting in a structure in which layers of 5-benzoyl-4-hydroxy-2-methoxybenzene groups are separated by ionic hydrogen-bonded sheets. Each methanol molecule forms a hydrogen bond to one of the sulfonate O atoms, resulting in this oxygen forming a total of three hydrogen bonds, and fills void volume between the interdigitated 5-benzoyl-4-hydroxy-2-methoxybenzene groups of neighboring sheets. The benzophenone hydroxyl proton forms an intramolecular hydrogen bond to the carbonyl oxygen.

AB - Guanidinium 5-benzoyl-4-hydroxy-2-methoxybenzene-sulfonate methanol solvate [C(NH2)3+.(C14H11O 3)SO3-.-CH3OH] crystallizes into a layered structure containing a two-dimensional hydrogen-bonded network typical of guanidinium alkane- and arenesulfonates. All six guanidinium protons and six sulfonate oxygen lone-pair acceptors participate in hydrogen bonding to form nearly planar pseudohexagonal hydrogen-bonded sheets, which can be viewed as parallel connected hydrogen-bonded ribbons. The 5-benzoyl-4-hydroxy-2-methoxybenzene groups are oriented to the same side of each ribbon, but the orientation of these groups on adjacent ribbons alternates with respect to the hydrogen-bonded sheet. The planar sheets stack with interdigitation of the arene groups, resulting in a structure in which layers of 5-benzoyl-4-hydroxy-2-methoxybenzene groups are separated by ionic hydrogen-bonded sheets. Each methanol molecule forms a hydrogen bond to one of the sulfonate O atoms, resulting in this oxygen forming a total of three hydrogen bonds, and fills void volume between the interdigitated 5-benzoyl-4-hydroxy-2-methoxybenzene groups of neighboring sheets. The benzophenone hydroxyl proton forms an intramolecular hydrogen bond to the carbonyl oxygen.

UR - http://www.scopus.com/inward/record.url?scp=0000692189&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000692189&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0000692189

VL - 52

SP - 209

EP - 214

JO - Acta Crystallographica Section B: Structural Science

JF - Acta Crystallographica Section B: Structural Science

SN - 0108-7681

IS - 1

ER -