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Hydrogen-bonded co-crystal structure of benzoic acid and zwitterionic l-proline.

ABSTRACT: The title compound [systematic name: benzoic acid-pyrrolidin-1-ium-2-carboxyl-ate (1/1)], C₇H₆O₂·C₅H₉NO₂, is an example of the application of non-centrosymmetric co-crystallization for the growth of a crystal containing a typically centrosymmetric component in a chiral space group. It co-crystallizes in the space group P2₁2₁2₁ and contains benzoic acid and l-proline in equal proportions. The crystal structure exhibits chains of l-proline zwitterions capped by benzoic acid mol-ecules which form a C(5)[R₃³(11)] hydrogen-bonded network along [100]. The crystal structure is examined and compared to that of a similar co-crystal containing l-proline zwitterions and 4-amino-benzoic acid.

SUBMITTER: Chesna AM

PROVIDER: S-EPMC5347056 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Hydrogen-bonded co-crystal structure of benzoic acid and zwitterionic l-proline.

Chesna Aaron M AM Cox Jordan M JM Basso Sanjukta S Benedict Jason B JB

Acta crystallographica. Section E, Crystallographic communications 20170214 Pt 3

The title compound [systematic name: benzoic acid-pyrrolidin-1-ium-2-carboxyl-ate (1/1)], C7H6O2·C5H9NO2, is an example of the application of non-centrosymmetric co-crystallization for the growth of a crystal containing a typically centrosymmetric component in a chiral space group. It co-crystallizes in the space group P212121 and contains benzoic acid and l-proline in equal proportions. The ...[more]

PMID: 28316811

Similar Datasets

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

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

Project description: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.

| S-EPMC6323886 | biostudies-literature

Crystal structure of 3-ethynyl-benzoic acid.

Project description:In the title compound, C9H6O2, the carb-oxy-lic acid group is almost in the plane of the benzene ring, making a dihedral angle of 2.49 (18)°. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming classical acid-acid inversion dimers, with an R 2 (2)(8) ring motif. The dimers are linked by pairs of C-H⋯O hydrogen bonds forming chains, enclosing R 2 (2)(16) ring motifs, propagating along the c-axis direction.

| S-EPMC4647427 | biostudies-literature

Crystal structure of a 2:1 piroxicam-gentisic acid co-crystal featuring neutral and zwitterionic piroxicam mol-ecules.

Project description:A new 2:1 co-crystal of piroxicam and gentisic acid [systematic name: 4-hy-droxy-1,1-dioxo-N-(pyridin-2-yl)-2H-1?6,2-benzo-thia-zine-3-carboxamide-2-(4-oxido-1,1-dioxo-2H-1?6,2-benzo-thia-zine-3-amido)-pyridin-1-ium-2,5-di-hydroxy-benzoic acid, 2C15H13N3O4S·C7H6O4] has been synthesized using a microfluidic platform and initially identified using Raman spectroscopy. In the co-crystal, one piroxicam mol-ecule is in its neutral form and an intra-molecular O-H?O hydrogen bond is observed. The other piroxicam mol-ecule is zwitterionic (proton transfer from the OH group to the pyridine N atom) and two intra-molecular N-H?O hydrogen bonds occur. The gentisic acid mol-ecule shows whole-mol-ecule disorder over two sets of sites in a 0.809?(2):0.191?(2) ratio. In the crystal, extensive hydrogen bonding between the components forms layers propagating in the ab plane.

| S-EPMC5137592 | 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

Crystal structure of 2-(4-chloro-benzamido)-benzoic acid.

Project description:In the title mol-ecule, C14H10ClNO3, the amide C=O bond is anti to the o-carb-oxy substituent in the adjacent benzene ring, a conformation that facilitates the formation of an intra-molecular amide-N-H?O(carbon-yl) hydrogen bond that closes an S(6) loop. The central amide segment is twisted away from the carb-oxy- and chloro-substituted benzene rings by 13.93?(17) and 15.26?(15)°, respectively. The most prominent supra-molecular inter-actions in the crystal packing are carb-oxy-lic acid-H?O(carbox-yl) hydrogen bonds that lead to centrosymmetric dimeric aggregates connected by eight-membered {?HOC=O}2 synthons.

| S-EPMC4645063 | biostudies-literature

Crystal structure of 4-(tri-methyl-germ-yl)benzoic acid.

Project description:The title compound, [Ge(CH3)3(C7H5O2)], was obtained as a by-product in the synthesis of the corresponding aldehyde. Two slightly different mol-ecules are present in the asymmetric unit. In both mol-ecules, the geometry of the aromatic ring plane is distorted by varying intensities. Additionally, the Ge atoms deviate from the mean aromatic ring planes. Whereas the distance of the Ge atom to the ring plane is only 0.101?(4)?Å in the first mol-ecule, this distance is increased to 0.210?(4)?Å in the second. In the crystal structure, centrosymmetric O-H?O hydrogen-bonded dimers are formed. The title compound is isostructural with the Si analogue [Haberecht et al. (2004 ?). Acta Cryst. E60, o329-0330].

| S-EPMC4459299 | 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 ?-? inter-actions exist at a centroid-centroid distance of 3.8423?(15)?Å between the benzene rings. An extremely weak C-H?? inter-action also is present.

| S-EPMC4459298 | 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 3-acet-oxy-2-methyl-benzoic acid.

Project description:In the title mol-ecule, C10H10O4, the carb-oxy-lic acid group is twisted by 11.37 (15)° from the plane of the benzene ring and the acet-oxy group is twisted from this plane by 86.60 (17)°. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers with the expected R 2 (2)(8) graph-set motif.

| S-EPMC4518910 | biostudies-literature

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