Crystal structure of 1-{(E)-[(3,4-di-chloro-phen-yl)imino]-meth-yl}naphthalen-2-ol.

In the title compound, C17H11Cl2NO, the dihedral angle between the planes of the naphthalene ring system and the benzene ring is 28.88 (11)°. The main twist in the mol-ecule occurs about the N-Cb (b = benzene ring) bond, as indicated by the C=N-Cb-Cb torsion angle of 31.0 (4)°. An intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of very weak C-H⋯O inter-actions generate R 2 (2)(16) loops.

Crystal structure of 4-chloro-2-{(E)-[(3,4-di-methyl-phen-yl)imino]-meth-yl}phenol.

In the title compound, C15H14ClNO, which is isostructural with its bromo analogue [Tahir et al. (2012 ▶). Acta Cryst., E68, o2730], the dihedral angle between the planes of the aromatic rings is 2.71 (7)° and an intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. In the crystal, extremely weak C-H⋯π inter-actions link the mol-ecules into a three-dimensional network.

1-{[(E)-(4-{[(2Z)-2,3-Di-hydro-1,3-thia-zol-2-yl-idene]sulfamo-yl}phen-yl)iminium-yl]meth-yl}naphthalen-2-olate.

In the title zwitterionic compound, C20H15N3O3S2, the 2-hy-droxy-naphthalene-1-carbaldehyde group A, the anilinic unit B and the 1,3-thia-zol-2(3H)-imine group C are each approximately planar with r.m.s. deviation of 0.0721, 0.0412 and 0.0125 Å, respectively. The dihedral angles between A/B, A/C and B/C are 24.70 (10), 79.97 (7) and 83.14 (6)°, respectively. There is an intra-molecular S(6) motif involving the imine N-H and the naphtho-late O atom. In the crystal, inversion-related mol-ecules form dimers as a result of N-H⋯N and N-H⋯O hydrogen bonds with R 2 (2)(8) and R 1 (2)(4) motifs, respectively. Weak π-π inter-actions between the benzene and naphthyl rings of inversion-related mol-ecules have ring centroid-centroid distances of 3.638 (2) and 4.041 (2) Å. A C-H⋯π inter-action occurs between the thia-zol ring and the benzene ring of an adjacent mol-ecule.

Synthesis, biological evaluation and molecular docking of N-phenyl thiosemicarbazones as urease inhibitors.

Urease is an important enzyme which breaks urea into ammonia and carbon dioxide during metabolic processes. However, an elevated activity of urease causes various complications of clinical importance. The inhibition of urease activity with small molecules as inhibitors is an effective strategy for therapeutic intervention. Herein, we have synthesized a series of 19 benzofurane linked N-phenyl semithiocarbazones (3a-3s). All the compounds were screened for enzyme inhibitor activity against Jack bean urease. The synthesized N-phenyl thiosemicarbazones had varying activity levels with IC50 values between 0.077 ± 0.001 and 24.04 ± 0.14 µM compared to standard inhibitor, thiourea (IC50 = 21 ± 0.11 µM). The activities of these compounds may be due to their close resemblance of thiourea. A docking study with Jack bean urease (PDB ID: 4H9M) revealed possible binding modes of N-phenyl thiosemicarbazones.

Crystal structure of 3-{(E)-[(3,4-di-chloro-phen-yl)imino]-meth-yl}benzene-1,2-diol.

In the title Schiff base, C13H9Cl2NO2, which arose from the condensation of 3,4-di-chloro-aniline with 2,3-di-hydroxy-benzaldehyde, the dihedral angle between the aromatic rings is 44.74 (13)°. Intra-molecular O-H⋯O and O-H⋯N hydrogen bonds close S(5) and S(6) rings, respectively. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (2)(10) loops. A weak C-H⋯π inter-action is also observed.

Crystal structure of (E)-2-[(4-hy-droxy-benzyl-idene)aza-nium-yl]benzoate.

The title Schiff base, C14H11NO3, crystallizes as a zwitterion (i.e. proton transfer from the carb-oxy-lic acid group to the imine N atom). The dihedral angle between the aromatic rings is 19.59 (6)° and an intra-molecular N-H⋯O hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (4)(24) loops. The dimers are linked by C-H⋯O inter-actions, generating (211) sheets.

Crystal structure of 4-(3-carb-oxy-pro-pan-amido)-2-hy-droxy-benzoic acid mono-hydrate.

In the title hydrate, C11H11NO6·H2O, the organic mol-ecule is approximately planar (r.m.s. deviation for the non-H atoms = 0.129 Å) and an intra-molecular O-H⋯O hydrogen bond closes an S(6) ring. In the crystal, the benzoic acid group participates in an O-H⋯O hydrogen bond to the water mol-ecule and accepts a similar bond from another water mol-ecule. The other -CO2H group forms a carb-oxy-lic acid inversion dimer, thereby forming an R 2 (2)(8) loop. These bonds, along with N-H⋯O and C-H⋯O inter-actions, generate a three-dimensional network.

N'-[(E)-4-Bromo-benzyl-idene]pyrazine-2-carbohydrazide.

In the title compound, C12H9BrN4O, the N'-methyl-idene-pyrazine-2-carbohydrazide and 4-bromobenzene groups are oriented at a dihedral angle of 10.57 (7)°. The hydrazide N-H group is involved in intra-molecular N-H⋯N inter-action, which generates an S(5) motif. A short C-H⋯O inter-action is formed between the methyl-idene H atom and the carbonyl O atom. It connects mol-ecules into chains extending along [100]. In addition, mol-ecules are arranged into stacks extending along [010] via π-π inter-actions between pyrazine and benzene rings, with centroid-centroid distances of 3.837 (2) and 3.860 (2) Å.

2-[(E)-({4-[(4,6-Dimethyl-pyrimidin-2-yl)sulfamo-yl]phen-yl}iminio)meth-yl]-6-hy-droxy-phenolate.

The title compound, C(19)H(18)N(4)O(4)S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihy-droxy-benzaldehyde fragment is oriented at a dihedral angle of 35.51 (11)° to the adajacent aniline group and makes a dihedral angle of 76.99 (6)° with the 4,6-dimethyl-pyrimidin-2-amine group. Intra-molecular O-H⋯O and N-H⋯O hydrogen bonds close S(5) and S(6) rings, respectively; the same O atom accepts both bonds. In the crystal, polymeric chains along [001] are formed from mol-ecules joined end-to-end by N-H⋯O and O-H⋯N hydrogen bonds; these feature R(2) (3)(6) loops. The polymeric chains are linked by C-H⋯O inter-actions and there are π-π inter-actions between the pyrimidine rings with a centroid-centroid distance of 3.446 (2) Å.

(2E)-2-(4-Hy-droxy-3-meth-oxy-benzyl-idene)hydrazinecarboxamide.

In the title compound, C(9)H(11)N(3)O(3), two mol-ecules are present in the asymmetric unit in which the 4-hy-droxy-3-meth-oxy-benzaldehyde and hydrazinecarboxamide units are almost planar [with r.m.s. deviations 0.0212 and 0.0066 Å, respectively, in one mol-ecule and 0.0346 and 0.0095 Å, respectively, in the other] and are oriented at dihedral angles of 9.7 (3) and 16.6 (3)°. In both mol-ecules, two S(5) ring motifs are present due to N-H⋯N and O-H⋯O hydrogen bonds. In the crystal, the mol-ecules are dimerized with each other due to pairs of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. O-H⋯O hydrogen bonds lead to the formation of a three-dimensional network.

3-[(E)-(Pyridin-3-yl-imino)-meth-yl]phenol.

Two independent mol-ecules are present in the asymmetric unit of the title compound, C(12)H(10)N(2)O, in which the 3-hy-droxy-benzaldehyde and the pyridin-3-amine units are almost planar [r.m.s. deviations of 0.0236 and 0.0116Å, respectively, in one mol-ecule and 0.0245 and 0.0162Å, respectively, in the other] and are oriented at dihedral angles of 7.21 (7) and 14.77 (7)°. In the crystal, mol-ecules of the same type form inversion dimers via pairs of O-H⋯N hydrogen bonds, forming R(2) (2)(20) ring motifs. There exist π-π inter-actions between the benzene and pyridine rings of molecules of the same type with centroid-centroid distances of 3.7127 (10) and 3.8439 (10) Å.

2-[(E)-3,4-Dimeth-oxy-benzyl-idene]hydrazinecarboxamide.

In the title compound, C(10)H(13)N(3)O(3), the 3,4-dimeth-oxy-benzyl-idene and hydrazinecarboxamide groups are oriented at a dihedral angle of 53.82 (6)° and an intra-molecular N-H⋯N hydrogen bond generates an S(5) ring motif. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into sheets propagating in (-201), which feature R(1) (2)(5), R(2) (2)(8) and R(2) (4)(14) loops.

2-{(E)-[(4-Methyl-phen-yl)imino]-meth-yl}-4-nitro-phenol-2-{(E)-[(4-methyl-phen-yl)iminio]meth-yl}-4-nitro-phenolate (0.60/0.40).

The crystal of the title compound, 0.6C(14)H(12)N(2)O(3)·0.4C(14)H(12)N(2)O(3), contains a mixture of its neutral (OH containing) and zwitterionic (NH containing) forms, in a 0.60 (4):0.40 (4) ratio. The former generates an S(6) loop via an intra-molecular O-H⋯N hydrogen bond and the latter generates an S(6) loop via an N-H⋯O hydro-gren bond. The aromatic rings are oriented at a dihedral angle of 42.52 (10)°. In the crystal, C-H⋯π inter-actions occur and aromatic π-π stacking inter-actions [centroid-centroid separations = 3.7106 (12) and 3.9177 (13) Å] consolidate the packing.

N-{4-[(E)-(4-Methyl-phen-yl)imino-meth-yl]phen-yl}acetamide.

There are two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(16)H(16)N(2)O, that differ in conformation. The dihedral angles between the benzene rings in the two mol-ecules are 44.35 (19) and 48.14 (17)°, but the rings twist in opposite directions. The acetamide groups make nearly equal dihedral angles of 25.4 (3) and 25.7 (3)° with the parent benzene rings. An S(6) ring motif is formed in each mol-ecule by intra-molecular C-H⋯O close contacts. In the crystal, strong N-H⋯O hydrogen bonds between acetamide groups generate a C(4) chain motif arranging the mol-ecules into two symmetry-independent polymeric structures extending along [010].

N-[(E)-2,4-Dichloro-benzyl-idene]-4-methyl-aniline.

In the title compound, C(14)H(11)Cl(2)N, the dihedral angle between the 4-methyl-anilinic and 2,4-dichloro-benzaldehyde moieties is 7.37 (8)°. In the crystal, C-H⋯π inter-actions between the terminal methyl group and a symmetry-related ring of the anilinic group help to establish the packing.

2-{[(E)-1,3-Benzodioxol-5-yl]methyl-idene-amino}-benzoic acid.

In the title compound, C(15)H(11)NO(4), the dihedral angle between the aromatic rings is 23.8 (2)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

(E)-1-(2-Nitro-benzyl-idene)-2-phenyl-hydrazine.

The asymmetric unit of the title compound, C(13)H(11)N(3)O(2), contains two mol-ecules with slightly different conformations: the dihedral angle between the aromatic rings is 13.01 (10)° in one mol-ecule and 14.05 (10)° in the other. Both mol-ecules feature short intra-molecular C-H⋯O contacts, which generate S(6) rings. In the crystal, both mol-ecules form inversion dimers linked by pairs of N-H⋯O hydrogen bonds, thereby generating R(2) (2)(16) rings.

5-[(E)-(2,6-Dichloro-benzyl-idene)amino]-2-hy-droxy-benzoic acid.

There are two geometrically different mol-ecules in the asymmetric unit of the title compound, C(14)H(9)Cl(2)NO(3). The 5-amino-2-hy-droxy-benzoic acid units [r.m.s. deviations of 0.0323 and 0.0414 Å] and 2,6-dichloro-benzaldehyde groups [r.m.s. deviations of 0.0285 and 0.0226 Å] are roughly planar and oriented at dihedral angles of 11.69 (13) and 83.12 (6)° in the two mol-ecules. An intra-molecular O-H⋯O hydrogen bond completes an S(6) ring motif in each mol-ecule. The two mol-ecules form dimers with each other through inter-molecular O-H⋯N and C-H⋯O hydrogen bonds, completing an R(2) (2)(8) ring motif. The dimers are inter-linked via inter-molecular O-H⋯N and C-H⋯O hydrogen bonds, forming polymeric sheets.

N-[(E)-1,3-Benzodioxol-5-yl-methyl-idene]-4-methyl-aniline.

The two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(15)H(13)NO(2), differ in conformation, with the virtually planar 4-methyl-aniline (r.m.s. deviations of 0.0511 and 0.0082 Å) and piperonal groups (r.m.s. deviations of 0.0241 and 0.0486 Å) forming dihedral angles of 19.40 (5) and 42.90 (6)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯π inter-actions. The H atoms of the two methyl groups are disordered over two sets of sites of equal occupancy.

2-Hy-droxy-5-[(E)-(1H-indol-3-yl-methyl-idene)aza-nium-yl]benzoate.

The zwitterionic title compound, C(16)H(12)N(2)O(3), was obtained as a result of the condensation of 5-amino-salicylic acid and 1H-indole-3-carbaldehyde. The whole mol-ecule is roughly planar: the 4-hy-droxy-anilinic group and the 1H-indole-3-carbaldehyde moieties are only slightly twisted, making a dihedral angle of 7.77 (11)°, whereas, the carboxyl-ate group makes a dihedral angle of 3.34 (45)° with the parent 4-hy-droxy-anilinic group. S(6) ring motifs are formed due to intra-molecular O-H⋯O hydrogen bonding. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds build up pseudo-rings with R(1) (2)(4), R(2) (1)(7) and R(2) (2)(14) ring motifs. These pseudo-dimers are further linked by N-H⋯O hydrogen bonds into a chain extending along [101]. C-H⋯π inter-actions also occur, along with offset π-π inter-actions between the anilinic phenyl and the heterocyclic five-membered rings with a centroid-centroid distance of 3.5716 (19) Å.