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Crystal structure of 4-chloro-2-nitro-benzoic acid with 4-hy-droxy-quinoline: a disordered structure over two states of 4-chloro-2-nitro-benzoic acid-quinolin-4(1H)-one (1/1) and 4-hy-droxy-quinolinium 4-chloro-2-nitro-benzoate.

ABSTRACT: The title compound, C₉H_7.5NO·C₇H_3.5ClNO₄, was analysed as a disordered structure over two states, viz. co-crystal and salt, accompanied by a keto-enol tautomerization in the base mol-ecule. The co-crystal is 4-chloro-2-nitro-benzoic acid-quinolin-4(1H)-one (1/1), C₇H₄ClNO₄·C₉H₇NO, and the salt is 4-hy-droxy-quinolinium 4-chloro-2-nitro-benzoate, C₉H₈NO⁺·C₇H₃ClNO₄ ^-. In the compound, the acid and base mol-ecules are held together by a short hydrogen bond [O⋯O = 2.4393 (15) Å], in which the H atom is disordered over two positions with equal occupancies. In the crystal, the hydrogen-bonded acid-base units are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming a tape structure along the a-axis direction. The tapes are stacked into a layer parallel to the ab plane via π-π inter-actions [centroid-centroid distances = 3.5504 (8)-3.9010 (11) Å]. The layers are further linked by another C-H⋯O hydrogen bond, forming a three-dimensional network. Hirshfeld surfaces for the title compound mapped over shape-index and d _norm were generated to visualize the inter-molecular inter-actions.

SUBMITTER: Gotoh K

PROVIDER: S-EPMC6895935 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structures of 3-chloro-2-nitro-benzoic acid with quinoline derivatives: 3-chloro-2-nitro-benzoic acid-5-nitro-quinoline (1/1), 3-chloro-2-nitro-benzoic acid-6-nitro-quinoline (1/1) and 8-hy-droxy-quinolinium 3-chloro-2-nitro-benzoate.

Project description:The structures of three compounds of 3-chloro-2-nitro-benzoic acid with 5-nitro-quinoline, (I), 6-nitro-quinoline, (II), and 8-hy-droxy-quinoline, (III), have been determined at 190 K. In each of the two isomeric compounds, (I) and (II), C7H4ClNO4·C9H6N2O2, the acid and base mol-ecules are held together by O-H⋯N and C-H⋯O hydrogen bonds. In compound (III), C9H8NO+·C7H3ClNO4 -, an acid-base inter-action involving H-atom transfer occurs and the H atom is located at the N site of the base mol-ecule. In the crystal of (I), the hydrogen-bonded acid-base units are linked by C-H⋯O hydrogen bonds, forming a tape structure along the b-axis direction. Adjacent tapes, which are related by a twofold rotation axis, are linked by a third C-H⋯O hydrogen bond, forming wide ribbons parallel to the (03) plane. These ribbons are stacked via π-π inter-actions between the quinoline ring systems [centroid-centroid distances = 3.4935 (5)-3.7721 (6) Å], forming layers parallel to the ab plane. In the crystal of (II), the hydrogen-bonded acid-base units are also linked into a tape structure along the b-axis direction via C-H⋯O hydrogen bonds. Inversion-related tapes are linked by further C-H⋯O hydrogen bonds to form wide ribbons parallel to the (08) plane. The ribbons are linked by weak π-π inter-actions [centroid-centroid distances = 3.8016 (8)-3.9247 (9) Å], forming a three-dimensional structure. In the crystal of (III), the cations and the anions are alternately linked via N-H⋯O and O-H⋯O hydrogen bonds, forming a 21 helix running along the b-axis direction. The cations and the anions are further stacked alternately in columns along the a-axis direction via π-π inter-actions [centroid-centroid distances = 3.8016 (8)-3.9247 (9) Å], and the mol-ecular chains are linked into layers parallel to the ab plane through these inter-actions.

| S-EPMC6775735 | biostudies-literature

5-Chloro-2-hy-droxy-benzoic acid.

Project description:The asymmetric unit of the title compound, C(7)H(5)ClO(3), contains two mol-ecules; both feature an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, both mol-ecules form inversion dimers linked by pairs of O-H⋯O hydrogen bonds with R(2) (2)(8) ring motifs. The dimers are inter-linked by C-H⋯O inter-actions.

| S-EPMC3008994 | biostudies-literature

2-Chloro-4-nitro-benzoic acid-quinoline (1/1).

Project description:In the title compound, C(7)H(4)ClNO(4)·C(9)H(7)N, the two components are connected by an O-H⋯N hydrogen bond. In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of benzoic acid is 3.15 (7)°. In the crystal, units are linked by inter-molecular C-H⋯O hydrogen bonds, forming a tape along the c axis. The tapes are stacked along the b axis through a C-H⋯O hydrogen bond into a layer parallel to the bc plane.

| S-EPMC3247614 | biostudies-literature

Crystal structures of four isomeric hydrogen-bonded co-crystals of 6-methyl-quinoline with 2-chloro-4-nitro-benzoic acid, 2-chloro-5-nitro-benzoic acid, 3-chloro-2-nitro-benzoic acid and 4-chloro-2-nitro-benzoic acid.

Project description:The structures of the four isomeric compounds of 6-methyl-quinoline with chloro- and nitro-substituted benzoic acids, C7H4ClNO4·C10H9N, namely, 2-chloro-4-nitro-benzoic acid-6-methyl-quinoline (1/1), (I), 2-chloro-5-nitro-benzoic acid-6-methyl-quinoline (1/1), (II), 3-chloro-2-nitro-benzoic acid-6-methyl-quinoline (1/1), (III), and 4-chloro-2-nitro-benzoic acid-6-methyl-quinoline (1/1), (IV), have been determined at 185-190 K. In each compound, the acid and base mol-ecules are linked by a short hydrogen bond between a carboxyl O atom and an N atom of the base. The O⋯N distances are 2.5452 (12), 2.6569 (13), 2.5640 (17) and 2.514 (2) Å, respectively, for compounds (I)-(IV). In the hydrogen-bonded acid-base units of (I), (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.65 (3):0.35 (3), 0.59 (4):0.41 (4) and 0.48 (5):0.52 (5), respectively, for (I), (III) and (IV). The H atom in the hydrogen-bonded unit of (II) is located at the O-atom site. In all of the crystals of (I)-(IV), π-π inter-actions between the quinoline ring system and the benzene ring of the acid mol-ecule are observed. In addition, a π-π inter-action between the benzene rings of adjacent acid mol-ecules and a C-H⋯O hydrogen bond are observed in the crystal of (I), and C-H⋯O hydrogen bonds and O⋯Cl contacts occur in the crystals of (III) and (IV). These inter-molecular inter-actions connect the acid and base mol-ecules, forming a layer structure parallel to the bc plane in (I), a column along the a-axis direction in (II), a layer parallel to the ab plane in (III) and a three-dimensional network in (IV). Hirshfeld surfaces for the title compounds mapped over d norm and shape index were generated to visualize the weak inter-molecular inter-actions.

| S-EPMC7643240 | biostudies-literature

Crystal structures of the two isomeric hydrogen-bonded cocrystals 2-chloro-4-nitro-benzoic acid-5-nitro-quinoline (1/1) and 5-chloro-2-nitro-benzoic acid-5-nitro-quinoline (1/1).

Project description:The structures of two isomeric com-pounds of 5-nitro-quinoline with chloro- and nitro-substituted benzoic acid, namely, 2-chloro-4-nitro-benzoic acid-5-nitro-quinoline (1/1), (I), and 5-chloro-2-nitro-benzoic acid-5-nitro-quinoline (1/1), (II), both C7H4ClNO4·C9H6N2O2, have been determined at 190?K. In each com-pound, the acid and base mol-ecules are held together by an O-H?N hydrogen bond. In the crystal of (I), the hydrogen-bonded acid-base units are linked by a C-H?O hydrogen bond, forming a tape structure along [10]. The tapes are stacked into a layer parallel to the ab plane via N-O?? inter-actions between the nitro group of the base mol-ecule and the quinoline ring system. The layers are further linked by other C-H?O hydrogen bonds, forming a three-dimensional network. In the crystal of (II), the hydrogen-bonded acid-base units are linked into a wide ribbon structure running along [10] via C-H?O hydrogen bonds. The ribbons are further linked via another C-H?O hydrogen bond, forming a layer parallel to (110). Weak ?-? inter-actions [centroid-centroid distances of 3.7080?(10) and 3.7543?(9)?Å] are observed between the quinoline ring systems of adjacent layers. Hirshfeld surfaces for the 5-nitro-quinoline mol-ecules of the two com-pounds mapped over shape index and d norm were generated to visualize the weak inter-molecular inter-actions.

| S-EPMC6829746 | biostudies-literature

Quinolinium 8-hy-droxy-7-iodo-quinoline-5-sulfonate 0.8-hydrate.

Project description:In the crystal structure of the title hydrated quinolinium salt of ferron (8-hy-droxy-7-iodo-quinoline-5-sulfonic acid), C9H7N(+)·C9H5INO4S(-)·0.8H2O, the quinolinium cation is fully disordered over two sites (occupancy factors fixed at 0.63 and 0.37) lying essentially within a common plane and with the ferron anions forming π-π-associated stacks down the b axis [minimum ring centroid separation = 3.462 (6) Å]. The cations and anions are linked into chains extending along c through hy-droxy O-H⋯O and quinolinium N-H⋯O hydrogen bonds to sulfonate O-atom acceptors which are also involved in water O-H⋯O hydrogen-bonding inter-actions along b, giving a two-dimensional network.

| S-EPMC3588950 | biostudies-literature

Crystal structure of 3-bromo-2-hy-droxy-benzoic acid.

Project description:Mutual carbox-yl-carboxyl O-H?O hydrogen bonds link the mol-ecules of the title compound, C7H5BrO3, into centrosymmetric dimers which display a central R 2 (2)(8) ring motif. In addition, there is an intra-molecular hydrox-yl-carboxyl O-H?O inter-action present. A comparison with the crystal structures of 59 other substituted derivatives of salicylic acid shows that both the centrosymmetric carbox-yl-carboxyl O-H?O dimer and the stacking mode of mol-ecules along the short a axis observed in the title structure are frequent packing motifs in this set.

| S-EPMC4420063 | biostudies-literature

Crystal structure of 4-benzamido-2-hy-droxy-benzoic acid.

Project description:In the title compound, C14H11NO4, the dihedral angle between the mean planes of the aromatic rings is 3.96 (12)° and an intra-molecular O-H⋯O hydrogen bond closes an S(6) ring. A short intra-molecular C-H⋯O contact is also seen. In the crystal, carb-oxy-lic acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (2)(8) loops. Conversely, the N-H group does not form a hydrogen bond. Aromatic π-π inter-actions exist at a centroid-centroid distance of 3.8423 (15) Å between the benzene rings. An extremely weak C-H⋯π inter-action also is present.

| S-EPMC4459298 | biostudies-literature

Crystal structures of iso-quinoline-3-chloro-2-nitro-benzoic acid (1/1) and isoquinolinium 4-chloro-2-nitro-benzoate.

Project description:In each of the title isomeric compounds, C9H7.3N·C7H3.7ClNO4, (I), and C9H8N·C7H3ClNO4, (II), of iso-quinoline with 3-chloro-2-nitro-benzoic acid and 4-chloro-2-nitro-benzoic acid, the two components are linked by a short hydrogen bond between a base N atom and a carb-oxy O atom. In the hydrogen-bonded unit of (I), the H atom is disordered over two positions with N and O site occupancies of 0.30 (3) and 0.70 (3), respectively, while in (II), an acid-base inter-action involving H-atom transfer occurs and the H atom is located at the N site. In the crystal of (I), the acid-base units are connected through C-H⋯O hydrogen bonds into a tape structure along the b-axis direction. Inversion-related adjacent tapes are further linked through π-π inter-actions [centroid-centroid distances = 3.6389 (7)-3.7501 (7) Å], forming a layer parallel to (001). In the crystal of (II), the acid-base units are connected through C-H⋯O hydrogen bonds into a ladder structure along the a-axis direction. The ladders are further linked by another C-H⋯O hydrogen bond into a layer parallel to (001).

| S-EPMC4331863 | biostudies-literature

4-Chloro-benzoic acid-quinoline (1/1).

Project description:In the title compound, C(7)H(5)ClO(2)·C(9)H(7)N, the 4-chloro-benzoic acid mol-ecule is almost planar, with a dihedral angle of 2.9?(14)° between the carb-oxy group and the benzene ring. In the crystal, the two components are connected by an O-H?N hydrogen bond. In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of the benzoic acid is 44.75?(4)°. The two components are further linked by inter-molecular C-H?O hydrogen bonds, forming a layer parallel to the ab plane.

| S-EPMC3011561 | biostudies-literature

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