Adenin-1-ium hydrogen isophthalate dimethylformamide monosolvate
Abstract
In the title proton-transfer organic salt, C5H6.3N5+·C8H4.7O4-·C3H7NO, the adeninium moiety is protonated at the N atom in the 1-position of the 6-amino-7H-purin-1-ium (adeninium) cation. In the solid state, the second acidic proton of isophthalic acid is partially transferred to the imidazole N atom of the adeninium cation [refined O-H versus N-H ratio = 0.70 (11):0.30 (11)]. Through the partially transferred proton, the adeninium cation is strongly hydrogen bonded (N-H...O/O-H...N) to the isophthalate anion. This strong interaction is assisted by another N-H...O hydrogen bond originating from the adeninium NH2 group towards the isophthalate keto O atom, with an R22(8) graph-set motif. This arrangement is linked via N-H...O hydrogen bonds to the O atoms of the carboxylate group of an isophthalate anion. Together, these hydrogen bonds lead to the formation criss-cross zigzag isophthalate...adeninium chains lying parallel to (501) and (50-1). The adeninium cations and the isophthalate anions are arranged in infinite [pi] stacks that extend along the c-axis direction [interplanar distance = 3.305 (3) Å]. Molecules are inclined with respect to this direction and within the stacks they are offset by ca. half a molecule each. Combination of the N-H...O and O-H...N hydrogen bonds with the [pi]-[pi] interactions forms infinitely stacked isophthalate...adeniniummore »
- Authors:
-
- Youngstown State Univ., OH (United States). Dept. of Chemistry
- Publication Date:
- Research Org.:
- National Renewable Energy Lab. (NREL), Golden, CO (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
- OSTI Identifier:
- 1629720
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Acta Crystallographica. Section E
- Additional Journal Information:
- Journal Volume: 70; Journal Issue: 2; Journal ID: ISSN 1600-5368
- Publisher:
- International Union of Crystallography
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; single-crystal X-ray study; T = 100 K; mean (C–C) = 0.008 A˚; R factor = 0.088; wR factor = 0.233; data-to-parameter ratio = 15.5.
Citation Formats
Koteswara Rao, Vandavasi, Siddiqui, Tausif, Zeller, Matthias, and Lovelace-Cameron, Sherri R. Adenin-1-ium hydrogen isophthalate dimethylformamide monosolvate. United States: N. p., 2014.
Web. doi:10.1107/s1600536813034971.
Koteswara Rao, Vandavasi, Siddiqui, Tausif, Zeller, Matthias, & Lovelace-Cameron, Sherri R. Adenin-1-ium hydrogen isophthalate dimethylformamide monosolvate. United States. https://doi.org/10.1107/s1600536813034971
Koteswara Rao, Vandavasi, Siddiqui, Tausif, Zeller, Matthias, and Lovelace-Cameron, Sherri R. Sat .
"Adenin-1-ium hydrogen isophthalate dimethylformamide monosolvate". United States. https://doi.org/10.1107/s1600536813034971. https://www.osti.gov/servlets/purl/1629720.
@article{osti_1629720,
title = {Adenin-1-ium hydrogen isophthalate dimethylformamide monosolvate},
author = {Koteswara Rao, Vandavasi and Siddiqui, Tausif and Zeller, Matthias and Lovelace-Cameron, Sherri R.},
abstractNote = {In the title proton-transfer organic salt, C5H6.3N5+·C8H4.7O4-·C3H7NO, the adeninium moiety is protonated at the N atom in the 1-position of the 6-amino-7H-purin-1-ium (adeninium) cation. In the solid state, the second acidic proton of isophthalic acid is partially transferred to the imidazole N atom of the adeninium cation [refined O-H versus N-H ratio = 0.70 (11):0.30 (11)]. Through the partially transferred proton, the adeninium cation is strongly hydrogen bonded (N-H...O/O-H...N) to the isophthalate anion. This strong interaction is assisted by another N-H...O hydrogen bond originating from the adeninium NH2 group towards the isophthalate keto O atom, with an R22(8) graph-set motif. This arrangement is linked via N-H...O hydrogen bonds to the O atoms of the carboxylate group of an isophthalate anion. Together, these hydrogen bonds lead to the formation criss-cross zigzag isophthalate...adeninium chains lying parallel to (501) and (50-1). The adeninium cations and the isophthalate anions are arranged in infinite [pi] stacks that extend along the c-axis direction [interplanar distance = 3.305 (3) Å]. Molecules are inclined with respect to this direction and within the stacks they are offset by ca. half a molecule each. Combination of the N-H...O and O-H...N hydrogen bonds with the [pi]-[pi] interactions forms infinitely stacked isophthalate...adeninium chains, thus leading to a two-dimensional supramolecular structure with parallel interdigitating layers formed by the [pi] stacked isophthalate...adeninium chains. The DMF molecules of crystallization are bonded to the adeninium cations through strong N-H...O hydrogen bonds and project into the lattice space in between the anions and cations. There are also C-H...O hydrogen bonds present which, combined with the other interactions, form a three-dimensional network. The crystal under investigation was found to be split and was handled as if non-merohedrally twinned.},
doi = {10.1107/s1600536813034971},
journal = {Acta Crystallographica. Section E},
number = 2,
volume = 70,
place = {United States},
year = {Sat Jan 18 00:00:00 EST 2014},
month = {Sat Jan 18 00:00:00 EST 2014}
}
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