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A 1:2 co-crystal of 2,2'-di-thiodi-benzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: The asymmetric unit of the title 1:2 co-crystal, C14H10O4S2·2C7H6O2, comprises half a mol-ecule of di-thiodi-benzoic acid [systematic name: 2-[(2-carb-oxy-phen-yl)disulfan-yl]benzoic acid, DTBA], as the mol-ecule is located about a twofold axis of symmetry, and a mol-ecule of benzoic acid (BA). The DTBA mol-ecule is twisted about the di-sulfide bond [the C-S-S-C torsion angle is -83.19?(8)°] resulting in a near perpendicular relationship between the benzene rings [dihedral angle = 71.19?(4)°]. The carb-oxy-lic acid group is almost co-planar with the benzene ring to which it is bonded [dihedral angle = 4.82?(12)°]. A similar near co-planar relationship pertains for the BA mol-ecule [dihedral angle = 3.65?(15)°]. Three-mol-ecule aggregates are formed in the crystal whereby two BA mol-ecules are connected to a DTBA mol-ecule via hy-droxy-O-H?O(hydroxy) hydrogen bonds and eight-membered {?HOC=O}2 synthons. These are connected into a supra-molecular layer in the ab plane through C-H?O inter-actions. The inter-actions between layers to consolidate the three-dimensional architecture are ?-? stacking inter-actions between DTBA and BA rings [inter-centroid separation = 3.8093?(10)?Å] and parallel DTBA-hy-droxy-O??(BA) contacts [O?ring centroid separation = 3.9049?(14)?Å]. The importance of the specified inter-actions as well as other weaker contacts, e.g. ?-? and C-H?S, are indicated in the analysis of the calculated Hirshfeld surface and inter-action energies.

SUBMITTER: Tan SL

PROVIDER: S-EPMC6323886 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Publications

A 1:2 co-crystal of 2,2'-di-thiodi-benzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study.

Tan Sang Loon SL Tiekink Edward R T ERT

Acta crystallographica. Section E, Crystallographic communications 20190101 Pt 1

The asymmetric unit of the title 1:2 co-crystal, C14H10O4S2·2C7H6O2, comprises half a mol-ecule of di-thiodi-benzoic acid [systematic name: 2-[(2-carb-oxy-phen-yl)disulfan-yl]benzoic acid, DTBA], as the mol-ecule is located about a twofold axis of symmetry, and a mol-ecule of benzoic acid (BA). The DTBA mol-ecule is twisted about the di-sulfide bond [the C-S-S-C torsion angle is -83.19 (8)°] resulting in a near perpendi ...[more]

PMID: 30713723

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Project description:The crystal structures of two ammonium salts of 2-amino-4-nitro-benzoic acid are described, namely di-methyl-aza-nium 2-amino-4-nitro-benzoate, C2H8N+·C7H5N2O4-, (I), and di-butyl-aza-nium 2-amino-4-nitro-benzoate, C8H20N+·C7H5N2O4-, (II). The asymmetric unit of (I) comprises a single cation and a single anion. In the anion, small twists are noted for the carboxyl-ate and nitro groups from the ring to which they are connected, as indicated by the dihedral angles of 11.45 (13) and 3.71 (15)°, respectively; the dihedral angle between the substituents is 7.9 (2)°. The asymmetric unit of (II) comprises two independent pairs of cations and anions. In the cations, different conformations are noted in the side chains in that three chains have an all-trans [(+)-anti-periplanar] conformation, while one has a distinctive kink resulting in a (+)-synclinal conformation. The anions, again, exhibit twists with the dihedral angles between the carboxyl-ate and nitro groups and the ring being 12.73 (6) and 4.30 (10)°, respectively, for the first anion and 8.1 (4) and 12.6 (3)°, respectively, for the second. The difference between anions in (I) and (II) is that in the anions of (II), the terminal groups are conrotatory, forming dihedral angles of 17.02 (8) and 19.0 (5)°, respectively. In each independent anion of (I) and (II), an intra-molecular amino-N-H⋯O(carboxyl-ate) hydrogen bond is formed. In the crystal of (I), anions are linked into a jagged supra-molecular chain by charge-assisted amine-N-H⋯O(carboxyl-ate) hydrogen bonds and these are connected into layers via charge-assisted ammonium-N-H⋯O(carboxyl-ate) hydrogen bonds. The resulting layers stack along the a axis, being connected by nitro-N-O⋯π(arene) and methyl-C-H⋯O(nitro) inter-actions. In the crystal of (II), the anions are connected into four-ion aggregates by charge-assisted amino-N-H⋯O(carboxyl-ate) hydrogen bonding. The formation of ammonium-N-H⋯O(carboxyl-ate) hydrogen bonds, involving all ammonium-N-H and carboxyl-ate O atoms leads to a three-dimensional architecture; additional C-H⋯O(nitro) inter-actions contribute to the packing. The Hirshfeld surface analysis confirms the importance of the hydrogen bonding in both crystal structures. Indeed, O⋯H/H⋯O inter-actions contribute nearly 50% to the entire Hirshfeld surface in (I).

Dataset Information

A 1:2 co-crystal of 2,2'-di-thiodi-benzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study.

Publications

A 1:2 co-crystal of 2,2'-di-thiodi-benzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study.

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