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Crystal structure of 3-(2-hy ­ droxy ­ eth ­ yl)-2-methyl ­ sulfanyl-6-nitro-3 H -benzimidazol-1-ium chloride monohydrate

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ABSTRACT

In the cation of the title hydrated molecular salt, C10H12N3O3S+·Cl−·H2O, the benzimidazolium ring system is almost planar (r.m.s. deviation = 0.006 Å) and the nitro group is inclined at an angle of 4.86 (9)° to this plane. In the crystal, C—H⋯O hydrogen bonds form centrosymmetric R22(20) dimers and these are further aggregated through N—H⋯O and O—H⋯Cl hydrogen bonds involving the water mol­ecules and chloride anions. Aromatic π–π stacking inter­actions are also found between two parallel benzene rings or the benzene and imidazolium rings, with centroid–centroid distances of 3.5246 (9) and 3.7756 (9) Å, respectively. Analysis of the bond lengths and comparison with related compounds show that the nitro substituent is not involved in conjugation with the adjacent π-system and hence has no effect on the charge distribution of the heterocyclic ring.

No MeSH data available.


The mol­ecular packing of (I), showing the pattern formed by the water mol­ecules hydrogen bonded to the chloride anions.
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fig3: The mol­ecular packing of (I), showing the pattern formed by the water mol­ecules hydrogen bonded to the chloride anions.

Mentions: In the crystal, C14—H14B⋯O8 hydrogen bonds (Table 1 ▸) link the organic fragments into centrosymmetric dimers with (20) ring motifs along the [100] direction (Fig. 2 ▸). These dimers are further connected along the [100] and [010] directions by N—H⋯O and O—H⋯Cl hydrogen bonds, respectively, generating (22) rings. In the latter ring motifs, both the water mol­ecule and the oxygen atom of the hy­droxy­ethyl substituent act as donors with the chloride anion as acceptor. The O3 atom of the water mol­ecule serves as acceptor for the H9 atom of the imidazolium NH group (Fig. 3 ▸). The pattern formed by the water mol­ecules connecting the chloride anions, and forming an (8) ring, is reminiscent of a parallelogram (Fig. 3 ▸). The supra­molecular aggregation is completed by π–π stacking inter­actions between two parallel benzene rings and between the benzene and imidazolium rings: Cg2⋯Cg2(1 − x, −y, −z) = 3.5246 (9), Cg1⋯Cg2(1 − x, −y, −z) = 3.7756 (9) Å, slippage = 1.190 Å Cg1 and Cg2 are the centroids of the imidazolium and benzene rings respectively. The centroid–centroid separations are less than 3.8 Å, the maximum regarded as suitable for an effective π–π inter­action (Janiak, 2000 ▸) (Fig. 4 ▸)).


Crystal structure of 3-(2-hy ­ droxy ­ eth ­ yl)-2-methyl ­ sulfanyl-6-nitro-3 H -benzimidazol-1-ium chloride monohydrate
The mol­ecular packing of (I), showing the pattern formed by the water mol­ecules hydrogen bonded to the chloride anions.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5120724&req=5

fig3: The mol­ecular packing of (I), showing the pattern formed by the water mol­ecules hydrogen bonded to the chloride anions.
Mentions: In the crystal, C14—H14B⋯O8 hydrogen bonds (Table 1 ▸) link the organic fragments into centrosymmetric dimers with (20) ring motifs along the [100] direction (Fig. 2 ▸). These dimers are further connected along the [100] and [010] directions by N—H⋯O and O—H⋯Cl hydrogen bonds, respectively, generating (22) rings. In the latter ring motifs, both the water mol­ecule and the oxygen atom of the hy­droxy­ethyl substituent act as donors with the chloride anion as acceptor. The O3 atom of the water mol­ecule serves as acceptor for the H9 atom of the imidazolium NH group (Fig. 3 ▸). The pattern formed by the water mol­ecules connecting the chloride anions, and forming an (8) ring, is reminiscent of a parallelogram (Fig. 3 ▸). The supra­molecular aggregation is completed by π–π stacking inter­actions between two parallel benzene rings and between the benzene and imidazolium rings: Cg2⋯Cg2(1 − x, −y, −z) = 3.5246 (9), Cg1⋯Cg2(1 − x, −y, −z) = 3.7756 (9) Å, slippage = 1.190 Å Cg1 and Cg2 are the centroids of the imidazolium and benzene rings respectively. The centroid–centroid separations are less than 3.8 Å, the maximum regarded as suitable for an effective π–π inter­action (Janiak, 2000 ▸) (Fig. 4 ▸)).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the cation of the title hydrated molecular salt, C10H12N3O3S+·Cl−·H2O, the benzimidazolium ring system is almost planar (r.m.s. deviation = 0.006 Å) and the nitro group is inclined at an angle of 4.86 (9)° to this plane. In the crystal, C—H⋯O hydrogen bonds form centrosymmetric R22(20) dimers and these are further aggregated through N—H⋯O and O—H⋯Cl hydrogen bonds involving the water mol­ecules and chloride anions. Aromatic π–π stacking inter­actions are also found between two parallel benzene rings or the benzene and imidazolium rings, with centroid–centroid distances of 3.5246 (9) and 3.7756 (9) Å, respectively. Analysis of the bond lengths and comparison with related compounds show that the nitro substituent is not involved in conjugation with the adjacent π-system and hence has no effect on the charge distribution of the heterocyclic ring.

No MeSH data available.