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Title: 4,4'-([4,4'-Bipyridine]-1,1'-diium-1,1'-diyl)dibenzoate dihydrate

We report here the synthesis of a neutral viologen derivative, C 24H 16N 2O 4·2H 2O. The non-solvent portion of the structure (Z-Lig) is a zwitterion, consisting of two positively charged pyridinium cations and two negatively charged carboxylate anions. The carboxylate group is almost coplanar [dihedral angle = 2.04 (11)°] with the benzene ring, whereas the dihedral angle between pyridine and benzene rings is 46.28 (5)°. TheZ-Lig molecule is positioned on a center of inversion (Fig. 1). The presence of the twofold axis perpendicular to thec-glide plane in space groupC2/c generates a screw-axis parallel to thebaxis that is shifted from the origin by 1/4 in theaandcdirections. This screw-axis replicates the molecule (and solvent water molecules) through space. TheZ-Lig molecule links to adjacent moleculesviaO—H...O hydrogen bonds involving solvent water molecules as well as intermolecular C—H...O interactions. There are also π–π interactions between benzene rings on adjacent molecules.
Authors:
 [1] ;  [1] ;  [1] ;  [2] ;  [2]
  1. Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Publication Date:
Report Number(s):
SAND-2016-0459J
Journal ID: ISSN 2414-3146; IUCRBK; PII: S2414314616009664
Grant/Contract Number:
AC04-94AL85000
Type:
Accepted Manuscript
Journal Name:
IUCrData
Additional Journal Information:
Journal Volume: 1; Journal Issue: 6; Journal ID: ISSN 2414-3146
Research Org:
Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)
Sponsoring Org:
USDOE National Nuclear Security Administration (NNSA)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1248574

Rodriguez, Mark A., Sava Gallis, Dorina F., Chavez, James S., Klivansky, Liana M., and Liu, Yi. 4,4'-([4,4'-Bipyridine]-1,1'-diium-1,1'-diyl)dibenzoate dihydrate. United States: N. p., Web. doi:10.1107/s2414314616009664.
Rodriguez, Mark A., Sava Gallis, Dorina F., Chavez, James S., Klivansky, Liana M., & Liu, Yi. 4,4'-([4,4'-Bipyridine]-1,1'-diium-1,1'-diyl)dibenzoate dihydrate. United States. doi:10.1107/s2414314616009664.
Rodriguez, Mark A., Sava Gallis, Dorina F., Chavez, James S., Klivansky, Liana M., and Liu, Yi. 2016. "4,4'-([4,4'-Bipyridine]-1,1'-diium-1,1'-diyl)dibenzoate dihydrate". United States. doi:10.1107/s2414314616009664. https://www.osti.gov/servlets/purl/1248574.
@article{osti_1248574,
title = {4,4'-([4,4'-Bipyridine]-1,1'-diium-1,1'-diyl)dibenzoate dihydrate},
author = {Rodriguez, Mark A. and Sava Gallis, Dorina F. and Chavez, James S. and Klivansky, Liana M. and Liu, Yi},
abstractNote = {We report here the synthesis of a neutral viologen derivative, C24H16N2O4·2H2O. The non-solvent portion of the structure (Z-Lig) is a zwitterion, consisting of two positively charged pyridinium cations and two negatively charged carboxylate anions. The carboxylate group is almost coplanar [dihedral angle = 2.04 (11)°] with the benzene ring, whereas the dihedral angle between pyridine and benzene rings is 46.28 (5)°. TheZ-Lig molecule is positioned on a center of inversion (Fig. 1). The presence of the twofold axis perpendicular to thec-glide plane in space groupC2/c generates a screw-axis parallel to thebaxis that is shifted from the origin by 1/4 in theaandcdirections. This screw-axis replicates the molecule (and solvent water molecules) through space. TheZ-Lig molecule links to adjacent moleculesviaO—H...O hydrogen bonds involving solvent water molecules as well as intermolecular C—H...O interactions. There are also π–π interactions between benzene rings on adjacent molecules.},
doi = {10.1107/s2414314616009664},
journal = {IUCrData},
number = 6,
volume = 1,
place = {United States},
year = {2016},
month = {6}
}

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