scholarly journals A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

2019 ◽  
Vol 75 (1) ◽  
pp. 1-7 ◽  
Author(s):  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Benzoic Acid ◽  
Dihedral Angle ◽  
Computational Study ◽  
Three Dimensional ◽  
Acid Group ◽  
Hirshfeld Surface ◽  
Carboxylic Acid Group ◽  
Title 1 ◽  
Axis Of Symmetry ◽  
Ring Centroid

The asymmetric unit of the title 1:2 co-crystal, C14H10O4S2·2C7H6O2, comprises half a molecule of dithiodibenzoic acid [systematic name: 2-[(2-carboxyphenyl)disulfanyl]benzoic acid, DTBA], as the molecule is located about a twofold axis of symmetry, and a molecule of benzoic acid (BA). The DTBA molecule is twisted about the disulfide 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 carboxylic 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 molecule [dihedral angle = 3.65 (15)°]. Three-molecule aggregates are formed in the crystal whereby two BA molecules are connected to a DTBA molecule via hydroxy-O—H...O(hydroxy) hydrogen bonds and eight-membered {...HOC=O}2 synthons. These are connected into a supramolecular layer in the ab plane through C—H...O interactions. The interactions between layers to consolidate the three-dimensional architecture are π–π stacking interactions between DTBA and BA rings [inter-centroid separation = 3.8093 (10) Å] and parallel DTBA-hydroxy-O...π(BA) contacts [O...ring centroid separation = 3.9049 (14) Å]. The importance of the specified interactions as well as other weaker contacts, e.g. π–π and C—H...S, are indicated in the analysis of the calculated Hirshfeld surface and interaction energies.

scholarly journals The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

2020 ◽  
Vol 76 (1) ◽  
pp. 102-110 ◽  
Author(s):  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Hydrogen Bonds ◽  
Benzoic Acid ◽  
Computational Study ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Molecular Structures ◽  
Amide Hydrogen ◽  
Title 1 ◽  
Crystal And Molecular Structures ◽  
Hirshfeld Surfaces

The crystal and molecular structures of the title 1:2 co-crystal, C14H14N4O2·2C7H6O2, are described. The oxalamide molecule has a (+)-antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central, almost planar C2N2O2 chromophore (r.m.s. deviation = 0.0555 Å). The benzoic acid molecules have equivalent, close to planar conformations [C6/CO2 dihedral angle = 6.33 (14) and 3.43 (10)°]. The formation of hydroxy-O—H...N(pyridyl) hydrogen bonds between the benzoic acid molecules and the pyridyl residues of the diamide leads to a three-molecule aggregate. Centrosymmetrically related aggregates assemble into a six-molecule aggregate via amide-N—H...O(amide) hydrogen bonds through a 10-membered {...HNC2O}2 synthon. These are linked into a supramolecular tape via amide-N—H...O(carbonyl) hydrogen bonds and 22-membered {...HOCO...NC4NH}2 synthons. The contacts between tapes to consolidate the three-dimensional architecture are of the type methylene-C—H...O(amide) and pyridyl-C—H...O(carbonyl). These interactions are largely electrostatic in nature. Additional non-covalent contacts are identified from an analysis of the calculated Hirshfeld surfaces.

scholarly journals A 2:1 co-crystal of 2-methylbenzoic acid andN,N′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis

2016 ◽  
Vol 72 (3) ◽  
pp. 391-398 ◽  
Author(s):  
Sabrina Syed ◽  
Mukesh M. Jotani ◽  
Siti Nadiah Abdul Halim ◽  
Edward R. T. Tiekink
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Three Dimensional ◽  
Acid Group ◽  
Hirshfeld Surface ◽  
Central Plane ◽  
Asymmetric Unit ◽  
Carboxylic Acid Group ◽  
Methyl Group ◽  
Central Residue

The asymmetric unit of the title 2:1 co-crystal, 2C8H8O2·C14H14N4O2, comprises an acid molecule in a general position and half a diamide molecule, the latter being located about a centre of inversion. In the acid, the carboxylic acid group is twisted out of the plane of the benzene ring to which it is attached [dihedral angle = 28.51 (8)°] and the carbonyl O atom and methyl group lie approximately to the same side of the molecule [hydroxy-O—C—C—C(H) torsion angle = −27.92 (17)°]. In the diamide, the central C4N2O2core is almost planar (r.m.s. deviation = 0.031 Å), and the pyridyl rings are perpendicular, lying to either side of the central plane [central residue/pyridyl dihedral angle = 88.60 (5)°]. In the molecular packing, three-molecule aggregates are formedviahydroxy-O—H...N(pyridyl) hydrogen bonds. These are connected into a supramolecular layer parallel to (12\overline{2})viaamide-N—H...O(carbonyl) hydrogen bonds, as well as methylene-C—H...O(amide) interactions. Significant π–π interactions occur between benzene/benzene, pyridyl/benzene and pyridyl/pyridyl rings within and between layers to consolidate the three-dimensional packing.

scholarly journals Crystal structure and Hirshfeld surface analysis of 1-carboxy-2-(3,4-dihydroxyphenyl)ethan-1-aminium bromide 2-ammonio-3-(3,4-dihydroxyphenyl)propanoate

2016 ◽  
Vol 72 (11) ◽  
pp. 1544-1548 ◽  
Author(s):  
Perumal Kathiravan ◽  
Thangavelu Balakrishnan ◽  
Perumal Venkatesan ◽  
Kandasamy Ramamurthi ◽  
María Judith Percino ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Rotation Axis ◽  
Three Dimensional ◽  
Acid Group ◽  
Hirshfeld Surface ◽  
Structure Parameter ◽  
Carboxylic Acid Group ◽  
Cationic Form ◽  
Absolute Structure ◽  
Molecular Salt

In the title molecular salt, C9H12NO4+·Br−·C9H11NO4, one of the dopa molecules is in the cationic form in which the α-amino group is protonated and the α-carboxylic acid group is uncharged, while the second dopa molecule is in the zwitterion form. The Br−anion occupies a special position and is located on a twofold rotation axis. The two dopa molecules are interconnected by short O—H...O hydrogen bonds. In the crystal, the various units are linked by O—H...O, N—H...Br and N—H...O hydrogen bonds, forming a three-dimensional framework. The title compound was refined as an inversion twin with an absolute structure parameter of 0.023 (8).

Crystal structure of 2-(2,6-Dichlorophenylcarbamoyl)benzoic acid

1982 ◽  
Vol 35 (9) ◽  
pp. 1933 ◽  
Author(s):  
CHL Kennard ◽  
G Smith ◽  
GF Katekar
Keyword(s):  
Crystal Structure ◽  
Benzoic Acid ◽  
Dihedral Angle ◽  
Acid Amide ◽  
Three Dimensional ◽  
Direct Methods ◽  
Acid Group ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
A Cell

The crystal structure of 2-(2,6-dichlorophenylcarbamoyl)benzoic acid has been determined by direct methods from three-dimensional X-ray diffraction data and refined to R 0.076 for 971 'observed' reflections. Crystals are monoclinic, space group P21/c with Z4 in a cell of dimensions a 12.150(6), b l3.629(6), c 8.368(4) �, β lO3.75(4)�. The molecules form centrosymmetric hydrogen-bonded cyclic dimers [O. . .O, 2.64(1) �] with the carboxylic acid group lying in the approximate plane of the attached benzene ring (dihedral angle 7.63�). This is in turn almost parallel to the 2,6-dichlorophenyl substituent group on the acid amide (dihedral angle 4.14�). The amide group is synclinally related to the ring systems in a similar way to that found in other phthalamic acids.

scholarly journals 2-Carboxylatopyridinium–4-nitrophenol (1/1)

2014 ◽  
Vol 70 (4) ◽  
pp. o450-o450 ◽  
Author(s):  
A. Sankar ◽  
S. Ambalatharasu ◽  
G. Peramaiyan ◽  
G. Chakkaravarthi ◽  
R. Kanagadurai
Keyword(s):  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Three Dimensional ◽  
Acid Group ◽  
Pyridine Molecule ◽  
Carboxylic Acid Group ◽  
Title 1 ◽  
Dimensional Network

In the title 1:1 adduct, C6H5NO3·C6H5NO2, both molecules are almost planar (r.m.s. deviations for the non-H atoms = 0.027 and 0.023 Å for 4-nitrophenol and 2-carboxylatopyridinium, respectively). The pyridine molecule crystallizes as a zwitterion (nominal proton transfer from the carboxylic acid group to the N atom in the ring). In the crystal, inversion dimers of the zwitterions linked by pairs of N—H...O hydrogen bonds generateR22(10) loops; two 4-nitrophenol molecules link to the dimer by O—H...O hydrogen bonds, generating a four-molecule aggregate. These are linked by C—H...O interactions, forming a three-dimensional network.

scholarly journals Bis{N′-[3-(4-nitrophenyl)-1-phenylprop-2-en-1-ylidene]-N-phenylcarbamimidothioato}zinc(II): crystal structure, Hirshfeld surface analysis and computational study

2021 ◽  
Vol 77 (8) ◽  
pp. 839-846
Author(s):  
Ming Yueh Tan ◽  
Huey Chong Kwong ◽  
Karen A. Crouse ◽  
Thahira B. S. A. Ravoof ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Dihedral Angle ◽  
Chelate Ring ◽  
Computational Study ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Dihedral Angles ◽  
Screw Axis ◽  
Ethylene Bond

The title zinc bis(thiosemicarbazone) complex, [Zn(C22H17N4O2S)2], comprises two N,S-donor anions, leading to a distorted tetrahedral N2S2 donor set. The resultant five-membered chelate rings are nearly planar and form a dihedral angle of 73.28 (3)°. The configurations about the endocyclic- and exocyclic-imine bonds are Z and E, respectively, and that about the ethylene bond is E. The major differences in the conformations of the ligands are seen in the dihedral angles between the chelate ring and nitrobenzene rings [40.48 (6) cf. 13.18 (4)°] and the N-bound phenyl and nitrobenzene ring [43.23 (8) and 22.64 (4)°]. In the crystal, a linear supramolecular chain along the b-axis direction features amine-N—H...O(nitro) hydrogen bonding. The chains assemble along the 21-screw axis through a combination of phenyl-C—H...O(nitro) and π(chelate ring)–π(phenyl) contacts. The double chains are linked into a three-dimensional architecture through phenyl-C—H...O(nitro) and nitro-O...π(phenyl) interactions.

scholarly journals 2,2′-(Disulfanediyl)dibenzoic acid N,N-dimethylformamide monosolvate: crystal structure, Hirshfeld surface analysis and computational study

2020 ◽  
Vol 76 (7) ◽  
pp. 1150-1157
Author(s):  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Benzene Ring ◽  
Computational Study ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Title 1 ◽  
Torsion Angles ◽  
Carboxylic Acid Groups ◽  
Hirshfeld Surfaces ◽  
Intermolecular Contacts ◽  
Benzene Rings

The title 1:1 solvate, C14H10O4S2·C3H7NO, features a twisted molecule of 2,2′-dithiodibenzoic acid (DTBA), with the central C—S—S—C torsion angle being −88.57 (6)°, and a molecule of dimethylformamide (DMF). The carboxylic acid groups are, respectively, close to co-planar and twisted with respect to the benzene rings to which they are connected as seen in the CO2/C6 torsion angles of 1.03 (19) and 7.4 (2)°. Intramolecular, hypervalent S←O interactions are noted [S...O = 2.6140 (9) and 2.6827 (9) Å]. In the crystal, four-molecule aggregates are formed via DTBA-O—H...O(DMF) and DTBA-O—H...O(DTBA) hydrogen bonding, the latter via an eight-membered {...OHCO}2 homosynthon. These are linked into supramolecular layers parallel to (011) via benzene-C—H...O(DTBA) and DTBA-C=O...π(benzene) interactions, with the connections between these, giving rise to a three-dimensional architecture, being of the type benzene-C—H...π(benzene). An analysis of the calculated Hirshfeld surfaces indicates, in addition to the aforementioned intermolecular contacts, the presence of stabilizing interactions between a benzene ring and a quasi-π-system defined by O—H...O hydrogen bonds between a DTBA dimer, i.e. the eight-membered {...OCOH}2 ring system, and between a benzene ring and a quasi-π(OCOH...OCH) system arising from the DTBA-O—H...O(DMF) hydrogen bond. The inter-centroid separations are 3.65 and 3.49 Å, respectively.

scholarly journals Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid

2020 ◽  
Vol 76 (6) ◽  
pp. 870-876
Author(s):  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Computational Study ◽  
Three Dimensional ◽  
Molecular Packing ◽  
Hirshfeld Surface ◽  
Pyridyl Ring ◽  
Chlorobenzoic Acid

The asymmetric unit of the title 1:2 co-crystal, C14H14N4O2·2C7H5ClO2, comprises a half-molecule of oxalamide (4 LH2), being located about a centre of inversion, and a molecule of3-chlorobenzoic acid (3-ClBA) in a general position. From symmetry, the 4 LH2 molecule has a (+)antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central, planar C2N2O2 chromophore with the dihedral angle between the core and pyridyl ring being 74.69 (11)°; intramolecular amide-N—H...O(amide) hydrogen bonds are noted. The 3-ClBA molecule exhibits a small twist as seen in the C6/CO2 dihedral angle of 8.731 (12)°. In the molecular packing, three-molecule aggregates are formed via carboxylic acid-O—H...N(pyridyl) hydrogen bonding. These are connected into a supramolecular tape along [111] through amide-N—H...O(carbonyl) hydrogen bonding. Additional points of contact between molecules include pyridyl and benzoic acid-C—H...O(amide), methylene-C—H...O(carbonyl) and C—Cl...π(pyridyl) interactions so a three-dimensional architecture results. The contributions to the calculated Hirshfeld surface are dominated by H...H (28.5%), H...O/O...H (23.2%), H...C/C...H (23.3%), H...Cl/Cl...H (10.0%) and C...Cl/C...Cl (6.2%) contacts. Computational chemistry confirms the C—Cl...π interaction is weak, and the importance of both electrostatic and dispersion terms in sustaining the molecular packing despite the strong electrostatic term provided by the carboxylic acid-O—H...N(pyridyl) hydrogen bonds.

scholarly journals Glycinium 3-carboxy-4-hydroxybenzenesulfonate

2014 ◽  
Vol 70 (4) ◽  
pp. o397-o397 ◽  
Author(s):  
A. Thirunavukkarasu ◽  
A. Silambarasan ◽  
R. Mohan Kumar ◽  
P. R. Umarani ◽  
G. Chakkaravarthi
Keyword(s):  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Dihedral Angle ◽  
Three Dimensional ◽  
Acid Group ◽  
Carboxylic Acid Group ◽  
Carboxylic Acid Groups ◽  
Dimensional Network

In the anion of the title salt, C2H6NO2+·C7H5O6S−, the dihedral angle between the carboxylic acid group and the benzene ring is 5.02 (12)°. In the crystal, the anions are linked into inversion dimers through pairs of O—H...O hydrogen bonds between the carboxylic acid groups and sulfonate O atoms. A pair of C—H...O interactions is also observed within each dimer. The anion dimers and the cations are linked into a three-dimensional network by N—H...O, O—H...O and C—H...O hydrogen bonds.

The inner salt 4-carboxy-2-(pyridinium-4-yl)-1H-imidazole-5-carboxylate monohydrate

2006 ◽  
Vol 62 (7) ◽  
pp. o2751-o2752 ◽  
Author(s):  
Ting Sun ◽  
Jian-Ping Ma ◽  
Ru-Qi Huang ◽  
Yu-Bin Dong
Keyword(s):  
Carboxylic Acid ◽  
Dihedral Angle ◽  
Title Compound ◽  
Acid Group ◽  
Planar Structure ◽  
Carboxyl Group ◽  
Carboxylic Acid Group ◽  
Pyridyl Group ◽  
Compound C

In the title compound, C10H7N3O4·H2O, one carboxyl group is deprotonated and the pyridyl group is protonated. The inner salt molecule has a planar structure, apart from the carboxylic acid group, which is tilted from the imidazole plane by a small dihedral angle of 7.3 (3)°.

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