scholarly journals Crystal structures of the two isomeric hydrogen-bonded cocrystals 2-chloro-4-nitrobenzoic acid–5-nitroquinoline (1/1) and 5-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1)

2019 ◽  
Vol 75 (11) ◽  
pp. 1694-1699
Author(s):  
Kazuma Gotoh ◽  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Shape Index ◽  
Quinoline Ring ◽  
Acid Base ◽  
Π Interactions ◽  
Bond Forming ◽  
Nitrobenzoic Acid ◽  
Base Units ◽  
Hydrogen Bonded

The structures of two isomeric compounds of 5-nitroquinoline with chloro- and nitro-substituted benzoic acid, namely, 2-chloro-4-nitrobenzoic acid–5-nitroquinoline (1/1), (I), and 5-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1), (II), both C7H4ClNO4·C9H6N2O2, have been determined at 190 K. In each compound, the acid and base molecules 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 [1\overline{2}0]. The tapes are stacked into a layer parallel to the ab plane via N—O...π interactions between the nitro group of the base molecule 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 [1\overline{1}0] 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 π–π interactions [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-nitroquinoline molecules of the two compounds mapped over shape index and d norm were generated to visualize the weak intermolecular interactions.

scholarly journals Crystal structures of 3-chloro-2-nitrobenzoic acid with quinoline derivatives: 3-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1), 3-chloro-2-nitrobenzoic acid–6-nitroquinoline (1/1) and 8-hydroxyquinolinium 3-chloro-2-nitrobenzoate

2019 ◽  
Vol 75 (10) ◽  
pp. 1552-1557 ◽  
Author(s):  
Kazuma Gotoh ◽  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bonds ◽  
Rotation Axis ◽  
Dimensional Structure ◽  
Acid Base ◽  
Base Interaction ◽  
Axis Direction ◽  
Π Interactions ◽  
Nitrobenzoic Acid ◽  
Base Units ◽  
Hydrogen Bonded

The structures of three compounds of 3-chloro-2-nitrobenzoic acid with 5-nitroquinoline, (I), 6-nitroquinoline, (II), and 8-hydroxyquinoline, (III), have been determined at 190 K. In each of the two isomeric compounds, (I) and (II), C7H4ClNO4·C9H6N2O2, the acid and base molecules are held together by O—H...N and C—H...O hydrogen bonds. In compound (III), C9H8NO+·C7H3ClNO4 −, an acid–base interaction involving H-atom transfer occurs and the H atom is located at the N site of the base molecule. 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 (\overline{1}03) plane. These ribbons are stacked via π–π interactions 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 (\overline{3}08) plane. The ribbons are linked by weak π–π interactions [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 interactions [centroid–centroid distances = 3.8016 (8)–3.9247 (9) Å], and the molecular chains are linked into layers parallel to the ab plane through these interactions.

scholarly journals Role of pK a in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids

2021 ◽  
Vol 77 (11) ◽  
Author(s):  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bond ◽  
Shape Index ◽  
Benzoic Acids ◽  
Quinoline Ring ◽  
Nitrobenzoic Acid ◽  
Layer Structures ◽  
Acid And Base ◽  
Short Hydrogen Bond ◽  
Substituted Benzoic Acids ◽  
Hydrogen Bonded

The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline (C10H9N) with chloro- and nitro-substituted benzoic acids (C7H4ClNO4), namely, 4-methylquinolinium 2-chloro-4-nitrobenzoate, C10H10N+·C7H3ClNO4 −, (I), 4-methylquinoline–2-chloro-5-nitrobenzoic acid (1/1), C10H9N·C7H4ClNO4, (II), 4-methylquinolinium 2-chloro-6-nitrobenzoate, C10H9.63N0.63+·C7H3.37ClNO4 0.63−, (III), 4-methylquinolinium 3-chloro-2-nitrobenzoate, C10H9.54N0.54+·C7H3.46ClNO4 0.54−, (IV), 4-methylquinolinium 4-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4 −, (V), and 4-methylquinolinium 5-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4 −, have been determined at 185–190 K. In each compound, the acid and base molecules are linked by a short hydrogen bond between a carboxy (or carboxylate) O atom and an N atom of the base. The O...N distances are 2.5652 (14), 2.556 (3), 2.5485 (13), 2.5364 (13), 2.5568 (13) and 2.5252 (11) Å, respectively, for compounds (I)–(VI). In the hydrogen-bonded acid–base units of (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.37 (3):0.63 (3) and 0.46 (3):0.54 (4), respectively, for (III) and (IV). The H atoms in the hydrogen-bonded units of (I), (V) and (VI) are located at the N-atom site, while the H atom in (II) is located at the O-atom site. In all the crystals of (I)–(VI), π–π stacking interactions between the quinoline ring systems and C—H...O hydrogen bonds are observed. Similar layer structures are constructed in (IV)–(VI) through these interactions together with π–π interactions between the benzene rings of the adjacent acid molecules. A short Cl...Cl contact and an N—O...π interaction are present in (I), while a C—H...Cl hydrogen bond and a π–π interaction between the benzene ring of the acid molecule and the quinoline ring system in (II), and a C—H...π interaction in (III) are observed. Hirshfeld surfaces for the title compounds mapped over d norm and shape index were generated to visualize the weak intermolecular interactions.

scholarly journals Crystal structures of threeN-(3-acetylphenyl)quinoline-2-carboxamides

2017 ◽  
Vol 73 (6) ◽  
pp. 804-808
Author(s):  
Diana Peña-Solórzano ◽  
Burkhard König ◽  
Cesar A. Sierra ◽  
Cristian Ochoa-Puentes
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Ring System ◽  
Molecular Structures ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Quinoline Ring ◽  
Π Interactions ◽  
Bond Forming

In the title compounds,N-(5-acetyl-2-methylphenyl)quinoline-2-carboxamide [C19H16N2O2, (I)],N-(5-acetyl-2-bromophenyl)quinoline-2-carboxamide [C18H13BrN2O2, (II)] andN-(5-acetyl-2-ethynylphenyl)quinoline-2-carboxamide [C20H14N2O2, (III)], the quinoline ring system is essentially planar and forms a dihedral angles of 3.68 (5) (I), 5.59 (7) (II) and 1.87 (6)° (III) with the acetyl-substituted ring. The molecular structures of (I) and (III) each feature an intramolecular N—H...N hydrogen bond, forming anS(5) ring, while in (II) an intramolecular bifurcated N—H...(N,Br) hydrogen bond forms twoS(5) rings. In the crystals, weak C—H...O hydrogen bonds link molecules of (I) intoC(7) chains long [010], molecules of (II) into chains ofR22(8) rings along [110] and molecules of (III) intoC(8) chains along [010]. In (I), there are no significant π–π stacking interactions under 4 Å, but in both (II) and (III), π–π interactions link the weak hydrogen-bonded chains into layers parallel to (001) [centroid–centroid disttances of 3.748 (1) Å in (II) and 3.577 (1), 3.784 (1) and 3.780 (1) Å in (III)].

scholarly journals Crystal structures of isoquinoline–3-chloro-2-nitrobenzoic acid (1/1) and isoquinolinium 4-chloro-2-nitrobenzoate

2015 ◽  
Vol 71 (1) ◽  
pp. 31-34 ◽  
Author(s):  
Kazuma Gotoh ◽  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Acid Base ◽  
Ladder Structure ◽  
Base Interaction ◽  
Axis Direction ◽  
Nitrobenzoic Acid ◽  
Short Hydrogen Bond ◽  
Base Units ◽  
Acid Base Interaction

In each of the title isomeric compounds, C9H7.3N·C7H3.7ClNO4, (I), and C9H8N·C7H3ClNO4, (II), of isoquinoline with 3-chloro-2-nitrobenzoic acid and 4-chloro-2-nitrobenzoic acid, the two components are linked by a short hydrogen bond between a base N atom and a carboxy 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 interaction 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 theb-axis direction. Inversion-related adjacent tapes are further linked through π–π interactions [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 thea-axis direction. The ladders are further linked by another C—H...O hydrogen bond into a layer parallel to (001).

scholarly journals Crystal structure of 1-benzyl-4-formyl-1H-pyrrole-3-carboxamide

2016 ◽  
Vol 72 (2) ◽  
pp. 133-135
Author(s):  
Qi-Di Zhong ◽  
Sheng-Quan Hu ◽  
Hong Yan
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Title Compound ◽  
Π Interactions ◽  
Bond Forming ◽  
Compound C ◽  
The Mean ◽  
Ring Motif

In the title compound, C13H12N2O2(I), the mean planes of the pyrrole and benzyl rings are approximately perpendicular, forming a dihedral angle of 87.07 (4) °. There is an intramolecular N—H...O hydrogen bond forming an S(7) ring motif. In the crystal, molecules are linkedviaa pair of N—H...O hydrogen bonds forming inversion dimers. C—H...O hydrogen bonds link the dimers into chains along direction [10-1]. The chains are further linked by weak C—H...π interactions forming layers parallel to theacplane.

scholarly journals Crystal structure of (ferrocenylmethyl)dimethylammonium hydrogen oxalate

2015 ◽  
Vol 71 (8) ◽  
pp. 947-949
Author(s):  
Mamadou Ndiaye ◽  
Abdoulaye Samb ◽  
Libasse Diop ◽  
Thierry Maris
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Π Interactions ◽  
Bond Forming ◽  
Linear Chains

The crystal structure of the title salt, [Fe(C5H5)(C8H13N)](HC2O4), consists of discrete (ferrocenylmethyl)dimethylammonium cations and hydrogen oxalate anions. The anions are connected through a strong O—H...O hydrogen bond, forming linear chains running parallel to [100]. The cations are linked to the anions through bifurcated N—H...(O,O′) hydrogen bonds. Weak C—H...π interactions between neighbouring ferrocenyl moieties are also observed.

scholarly journals (E)-2-[(Pyren-1-ylimino)methyl]quinolin-8-ol

IUCrData ◽  
2016 ◽  
Vol 1 (4) ◽  
Author(s):  
Soma Mukherjee ◽  
Shrabani Talukder ◽  
Helen Stoeckli-Evans
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Ring System ◽  
Quinoline Ring ◽  
Aromatic Rings ◽  
Π Interactions ◽  
Compound C ◽  
Centroid Distance ◽  
Ring Motif

In the title compound, C26H16N2O, the pyrene ring system (r.m.s. deviation = 0.021 Å) is inclined to the planar quinoline ring system (r.m.s. deviation = 0.017 Å) by 30.62 (5)°, and the conformation about the bridging N=C bond isE. There is an intramolecular O—H...N hydrogen bond with anS(5) ring motif present. In the crystal, molecules are linked by pairs of C—H...O hydrogen bonds, forming inversion dimers with anR22(14) ring motif, flanked by twoR21(7) ring motifs. The dimers stack along thebaxis with slipped parallel π–π interactions involving neighbouring molecules; the shortest π–π interaction involves aromatic rings of the quinoline ring system [inter-centroid distance = 3.6267 (11) Å].

scholarly journals Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2)

2018 ◽  
Vol 74 (12) ◽  
pp. 1727-1730 ◽  
Author(s):  
Kazuma Gotoh ◽  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Layer Structure ◽  
Asymmetric Unit ◽  
Acid Base ◽  
Chloranilic Acid ◽  
Base Interaction ◽  
Acid And Base ◽  
Acid Base Interaction ◽  
Hydrogen Bonded

The structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with ethyleneurea (systematic name: imidazolidin-2-one), C6H2Cl2O4·C3H6N2O, (I), and the 1:2 co-crystal of chloranilic acid with hydantoin (systematic name: imidazolidine-2,4-dione), C6H2Cl2O4·2C3H4N2O2, (II), have been determined at 180 K. In the crystals of both compounds, the base molecules are in the lactam form and no acid–base interaction involving H-atom transfer is observed. The asymmetric unit of (I) consists of two independent half-molecules of chloranilic acid, with each of the acid molecules lying about an inversion centre, and one ethyleneurea molecule. The asymmetric unit of (II) consists of one half-molecule of chloranilic acid, which lies about an inversion centre, and one hydantoin molecule. In the crystal of (I), the acid and base molecules are linked via O—H...O and N—H...O hydrogen bonds, forming an undulating sheet structure parallel to the ab plane. In (II), the base molecules form an inversion dimer via a pair of N—H...O hydrogen bonds, and the base dimers are further linked through another N—H...O hydrogen bond into a layer structure parallel to (\overline{1}01). The acid molecule and the base molecule are linked via an O—H...O hydrogen bond.

scholarly journals Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine

2017 ◽  
Vol 73 (10) ◽  
pp. 1546-1550 ◽  
Author(s):  
Kazuma Gotoh ◽  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Divalent Cations ◽  
Atom Transfer ◽  
Asymmetric Unit ◽  
Acid Base ◽  
Chloranilic Acid ◽  
Base Interaction ◽  
Hydrogen Bonded

The crystal structures of the 1:2 compounds of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine, namely, bis(2-pyridone) chloranilic acid, 2C5H5NO·C6H2Cl2O4, (I), bis(3-hydroxypyridinium) chloranilate, 2C5H6NO+·C6Cl2O42−, (II), and bis(4-hydroxypyridinium) chloranilate, 2C5H6NO+·C6Cl2O42−, (III), have been determined at 120 K. In the crystal of (I), the base molecule is in the lactam form and no acid–base interaction involving H-atom transfer is observed. The acid molecule lies on an inversion centre and the asymmetric unit consists of one half-molecule of chloranilic acid and one 2-pyridone molecule, which are linkedviaa short O—H...O hydrogen bond. 2-Pyridone molecules form a head-to-head dimerviaa pair of N—H...O hydrogen bonds, resulting in a tape structure along [201]. In the crystals of (II) and (III), acid–base interactions involving H-atom transfer are observed and the divalent cations lie on an inversion centre. The asymmetric unit of (II) consists of one half of a chloranilate anion and one 3-hydroxypyridinium cation, while that of (III) comprises two independent halves of anions and two 4-hydroxypyridinium cations. The primary intermolecular interaction in (II) is a bifurcated O—H...(O,O) hydrogen bond between the cation and the anion. The hydrogen-bonded units are further linkedviaN—H...O hydrogen bonds, forming a layer parallel to thebcplane. In (III), one anion is surrounded by four cationsviaO—H...O and C—H...O hydrogen bonds, while the other is surrounded by four cationsviaN—H...O and C—H...Cl hydrogen bonds. These interactions link the cations and the anions into a layer parallel to (301).

scholarly journals 4-Chloroanilinium 3-carboxyprop-2-enoate

2012 ◽  
Vol 68 (4) ◽  
pp. o959-o960 ◽  
Author(s):  
R. Anitha ◽  
S. Athimoolam ◽  
S. Asath Bahadur ◽  
M. Gunasekaran
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Amine Group ◽  
Asymmetric Unit ◽  
Aromatic Rings ◽  
Bond Forming ◽  
Compound C ◽  
Hydrogen Bonded

In the title compound, C6H7ClN+·C4H3O4−, the cations and anions lie on mirror planes and hence only half of the molecules are present in the asymmeric unit. The 4-chloroanilinium cation and hydrogen maleate anion in the asymmetric unit are each planar and are oriented at an angle of 15.6 (1)° to one another and perpendicular to thebaxis. A characterestic intramolecular O—H...O hydrogen bond, forming an S(7) motif, is observed in the maleate anion. In the crystal, the cations and anions are linked by N—H...O hydrogen bonds, forming layers in theabplane. The aromatic rings of the cations are sandwiched between hydrogen-bonded chains and rings formed through the amine group of the cation and maleate anions, leading to alternate hydrophobic (z= 0 or 1) and hydrophilic layers (z= 1/2) along thecaxis.

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