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Hydrazinium 2-amino-4-nitro ­ benzoate dihydrate: crystal structure and Hirshfeld surface analysis

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ABSTRACT

In the anion of the title salt hydrate, H5N2+·C7H5N2O4−·2H2O, the carboxyl­ate and nitro groups lie out of the plane of the benzene ring to which they are bound [dihedral angles = 18.80 (10) and 8.04 (9)°, respectively], and as these groups are conrotatory, the dihedral angle between them is 26.73 (15)°. An intra­molecular amino-N—H⋯O(carboxyl­ate) hydrogen bond is noted. The main feature of the crystal packing is the formation of a supra­molecular chain along the b axis, with a zigzag topology, sustained by charge-assisted water-O—H⋯O(carboxyl­ate) hydrogen bonds and comprising alternating twelve-membered {⋯OCO⋯HOH}2 and eight-membered {⋯O⋯HOH}2 synthons. Each ammonium-N—H atom forms a charge-assisted hydrogen bond to a water mol­ecule and, in addition, one of these forms a hydrogen bond with a nitro-O atom. The amine-N—H atoms form hydrogen bonds to carboxyl­ate-O and water-O atoms, and the amine N atom accepts a hydrogen bond from an amino-H atom. The hydrogen bonds lead to a three-dimensional architecture. An analysis of the Hirshfeld surface highlights the major contribution of O⋯H/H⋯O hydrogen bonding to the overall surface, i.e. 46.8%, compared with H⋯H contacts (32.4%).

No MeSH data available.


Two views of the Hirshfeld surface for (I) mapped over dnorm over the range −0.352 to 1.156 au.
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fig4: Two views of the Hirshfeld surface for (I) mapped over dnorm over the range −0.352 to 1.156 au.

Mentions: The Hirshfeld surface analysis of (I) provides additional insight into its mol­ecular packing and was performed in accord with a recent study of related ammonium salts (Wardell et al., 2016 ▸). The Hirshfeld surface mapped over electrostatic potential in Fig. 3 ▸ highlights the positive potential (blue region) around the hydrazinium cation and the negative potential (red) about the carboxyl­ate-oxygen atoms of the nitro­benzoate anion. The numerous bright-, diminutive- and faint-red spots appearing on the Hirshfeld surface mapped over dnorm in Fig. 4 ▸ are indicative of the variety of inter­molecular inter­actions in the crystal. The pair of charge-assisted water-O—H⋯O(carboxyl­ate) hydrogen bonds between the water-O—H2W and —H4W atoms and carboxyl­ate-O1 and -O2 atoms are evident through the bright-red spots appearing near the respective donor and acceptor atoms, Fig. 4 ▸a. The donors of these inter­actions appear as light-blue spots near the water O—H atoms and the acceptors as red regions surrounding carboxyl­ate-O1 and -O2 atoms on the Hirshfeld surface mapped over electrostatic potential in Fig. 3 ▸.


Hydrazinium 2-amino-4-nitro ­ benzoate dihydrate: crystal structure and Hirshfeld surface analysis
Two views of the Hirshfeld surface for (I) mapped over dnorm over the range −0.352 to 1.156 au.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382626&req=5

fig4: Two views of the Hirshfeld surface for (I) mapped over dnorm over the range −0.352 to 1.156 au.
Mentions: The Hirshfeld surface analysis of (I) provides additional insight into its mol­ecular packing and was performed in accord with a recent study of related ammonium salts (Wardell et al., 2016 ▸). The Hirshfeld surface mapped over electrostatic potential in Fig. 3 ▸ highlights the positive potential (blue region) around the hydrazinium cation and the negative potential (red) about the carboxyl­ate-oxygen atoms of the nitro­benzoate anion. The numerous bright-, diminutive- and faint-red spots appearing on the Hirshfeld surface mapped over dnorm in Fig. 4 ▸ are indicative of the variety of inter­molecular inter­actions in the crystal. The pair of charge-assisted water-O—H⋯O(carboxyl­ate) hydrogen bonds between the water-O—H2W and —H4W atoms and carboxyl­ate-O1 and -O2 atoms are evident through the bright-red spots appearing near the respective donor and acceptor atoms, Fig. 4 ▸a. The donors of these inter­actions appear as light-blue spots near the water O—H atoms and the acceptors as red regions surrounding carboxyl­ate-O1 and -O2 atoms on the Hirshfeld surface mapped over electrostatic potential in Fig. 3 ▸.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the anion of the title salt hydrate, H5N2+·C7H5N2O4−·2H2O, the carboxyl­ate and nitro groups lie out of the plane of the benzene ring to which they are bound [dihedral angles = 18.80 (10) and 8.04 (9)°, respectively], and as these groups are conrotatory, the dihedral angle between them is 26.73 (15)°. An intra­molecular amino-N—H⋯O(carboxyl­ate) hydrogen bond is noted. The main feature of the crystal packing is the formation of a supra­molecular chain along the b axis, with a zigzag topology, sustained by charge-assisted water-O—H⋯O(carboxyl­ate) hydrogen bonds and comprising alternating twelve-membered {⋯OCO⋯HOH}2 and eight-membered {⋯O⋯HOH}2 synthons. Each ammonium-N—H atom forms a charge-assisted hydrogen bond to a water mol­ecule and, in addition, one of these forms a hydrogen bond with a nitro-O atom. The amine-N—H atoms form hydrogen bonds to carboxyl­ate-O and water-O atoms, and the amine N atom accepts a hydrogen bond from an amino-H atom. The hydrogen bonds lead to a three-dimensional architecture. An analysis of the Hirshfeld surface highlights the major contribution of O⋯H/H⋯O hydrogen bonding to the overall surface, i.e. 46.8%, compared with H⋯H contacts (32.4%).

No MeSH data available.