Bioactive phenylpropanoid glycosides from Tabebuia avellanedae.

Three novel phenylpropanoid glycosides 2, 5, 6 were isolated from water extract of Tabebuia avellanedae, together with three known phenylpropanoid glycosides 1, 3, 4. All compounds were identified on the basis of spectroscopic analysis and chemical methods and, for known compounds, by comparison with published data. All isolated compounds showed strong antioxidant activity in the DPPH assay, and compound 5 give the highest antioxidant activity among all compounds, with an IC50 of 0.12 µM. All compounds exhibited moderate inhibitory effect on cytochrome CYP3A4 enzyme.

Poly[diammonium [(µ(4)-butane-1,2,3,4-tetra-carboxyl-ato)zincate] tetra-hydrate].

In the title compound, {(NH(4))(2)[Zn(C(8)H(6)O(8))]·4H(2)O}(n), the asymmetric unit contains one ammonium cation, half of a butane-1,2,3,4-tetra-carboxyl-ate anion, one Zn(2+) cation and two water mol-ecules. The butane-1,2,3,4-tetra-carboxyl-ate ligand is located about an inversion centre at the mid-point of the central C-C bond. The Zn(2+) cation is situated on a twofold rotation axis and is surrounded by four O atoms from four symmetry-related butane-1,2,3,4-tetra-carboxyl-ate anions in a distorted tetra-hedral environment. In turn, each anion coordinates to four Zn(2+) cations. The bridging mode of the anions leads to a three-dimensional framework structure with channels extending along [110] and [010] in which the ammonium cations and the water mol-ecules are located. N-H⋯O and O-H⋯O hydrogen bonding between the cations and water mol-ecules and the uncoordinating O atoms of the carboxyl-ate groups consolidates the crystal packing.

3,3'-(Piperazine-1,4-diium-1,4-di-yl)di-propionate dihydrate.

During the recrystallization of 3-[4-(2-carb-oxy-eth-yl)piperazin-1-yl]propionic acid, the carb-oxy-lic acid H atoms were transferred to the piperazine N atoms, forming the title compound, C(10)H(18)N(2)O(4)·2H(2)O, in which the zwitterion lies about an inversion center. In the crystal, bifurcated N-H⋯(O,O) hydrogen bonds connect the zwitterions into a two-dimensional framework parallel to (-102) forming R(4) (4)(30) rings. O-H⋯O hydrogen bonds involving the solvent water mol-ecules connect the two-dimensional framework into a three-dimensional network. In addition, weak C-H⋯O hydrogen bonds are observed.

3,5,3',5'-Tetra-methyl-4,4'-bi(1H-pyrazol-yl) hemihydrate.

In the title compound, C(10)H(14)N(4)·0.5H(2)O, the amino H atom of one of the two pyrazole rings is disordered over its two N atoms in a 1:1 ratio. The pyrazole rings are aligned at 60.1 (1)°. In the crystal, two bipyrazolyl mol-ecules are linked by an N-H⋯N hydrogen bond, generating a dimer; the dimer is connected to the water mol-ecule, which lies on a twofold rotation axis, resulting in the formation of a chain that makes an angle of ca 45.3 (1)° with the ab plane. The chains are cross-linked by N-H⋯O and O-H⋯N inter-actions, forming a three-dimensional network.

Bis(2-methyl-1H-benzimidazol-3-ium) naphthalene-1,5-disulfonate.

The asymmetric unit of the title compound, 2C(8)H(9)N(2) (+)·C(10)H(6)O(6)S(2) (2-), contains a 2-methyl-benzimidazolium cation and one half of a naphthalene-1,5-disulfonate anion. The formula unit is generated by an inversion center. In the crystal, N-H⋯O hydrogen bonds link the components into chains along [001]. In addition, weak C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions are observed. The methyl H atoms were refined as disordered over two sets of sites with equal occupancy.

6-Bromo-1,3-benzothia-zol-2-amine.

The r.m.s. deviation from the mean plane for the non-H atoms in the title compound, C(7)H(5)BrN(2)S, is 0.011 Å. In the crystal, the mol-ecules are linked by N-H⋯N and N-H⋯Br hydrogen bonds to generate (010) sheets. Weak aromatic π-π stacking [centroid-to-centroid separation = 3.884 (10) Å] and possible C-H⋯Br inter-actions are also observed. The crystal studied was found to be an inversion twin.

3-(Phenyl-carbamoyl)acrylic acid.

In the title compound, C(10)H(9)NO(3), the dihedral angle between the phenyl ring and the amide group is 10.8 (2)°. The C=O and O-H bonds of the carboxyl group adopt an anti orientation and an intra-molecular O-H⋯O hydrogen bond closes an S(7) ring. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into C(7) chains propagating in [101]. The packing is consolidated by C-H⋯O inter-actions, generating sheets aligned at an angle of ca 60° with the bc plane.

3,5-Dimethyl-pyrazolium 3,5-dinitro-salicylate.

In the title mol-ecular salt, C(5)H(9)N(2) (+)·C(7)H(3)N(2)O(7) (-), the roughly planar anion (r.m.s. deviation = 0.120 Å) has been deprotonated at the phenol group. An intra-molecular O-H⋯O hydrogen bond in the anion generates an S(6) ring. In the crystal, the components are linked by cation-to-anion N-H⋯O and N-H⋯(O,O) hydrogen bonds, generating [010] double chains. Weak C-H⋯O inter-actions consolidate the packing.

3,5-Dimethyl-1H-pyrazole-2-hy-droxy-5-(phenyl-diazen-yl)benzoic acid (1/1).

There are two independent 3,5-dimethyl-pyrazole and two independent 2-hy-droxy-5-(phenyl-diazen-yl)benzoic acid mol-ecules [in which intra-molecular O-H⋯O bonds form S(6) graph-set motifs] in the asymmetric unit of the title compound, C(5)H(8)N(2)·C(13)H(10)N(2)O(3). In the crystal, the components are linked by inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds, forming four-component clusters. Further stabilization is provided by weak C-H⋯π inter-actions.

5,13-Disulfamoyl-1,9-diazatetracyclo[7.7.1.0.0]heptadeca-2(7),3,5,10,12,14-hexaen-1-ium chloride.

In the title salt, C(15)H(17)N(4)O(4)S(2) (+)·Cl(-), the chloride anion is disordered over two positions with occupancies of 0.776 (6) and 0.224 (6). The cation adopts an L shape and the dihedral angle between the benzene rings is 82.5 (3)°. In the crystal, inversion dimers of cations linked by pairs of N-H⋯N hydrogen bonds occur, with the bond arising from the protonated N atom. The cationic dimers are linked into chains via the disordered chloride ions by way of N-H⋯Cl hydrogen bonds and N-H⋯O, C-H⋯O and C-H⋯Cl inter-actions also occur, which help to consolidate the three-dimensional network.

Bis(benzimidazol-1-yl)methane dihydrate.

The bis-(benzimidazol-1-yl)methane mol-ecule of the title compound, C(15)H(12)N(4)·2H(2)O, displays a trans conformation with a twofold axis running through the methylene C atom. Two adjacent water mol-ecules are bonded to this mol-ecule through O-H⋯N hydrogen bonds, forming a trimer. Adjacent trimers are connected together via C-H⋯O inter-actions, forming a chain running along the b-axis direction. Two such chains are joined together via π-π inter-actions [centroid-centroid distance = 3.556 (2) Å], forming double chains, which are connected via the water mol-ecules through C-H⋯O associations, forming a sheet structure. The sheets are stacked on top of each other along the a-axis direction and connected through O-H⋯O and C-H⋯O inter-actions, forming a three-dimensional ABAB layer network structure.

2-Methyl-1H-benzimidazol-3-ium hydrogen phthalate.

The asymmetric unit of the title compound, C(8)H(9)N(2) (+)·C(8)H(5)O(4) (-), contains two independent ion pairs. In each 2-methyl-1H-benzimidazolium ion, an intra-molecular O-H⋯O bond forms an S(7) graph-set motif. In the crystal, the components are linked by N-H⋯O hydrogen bonds, forming chains along [210]. Further stabilization is provided by weak C-H⋯O hydrogen bonds.

Oxonium picrate.

The title compound, H(3)O(+)·C(6)H(2)N(3)O(7) (-), consists of one picrate anion and one oxonium cation. The oxonium cation is located on a crystallographic twofold axis and both its H atoms are disordered, each over two symmetry-equivalent positions with occupancy ratios of 0.75. The picrate anions are also located on twofold axes bis-ecting the phenolate and p-nitro groups. π-π inter-actions between the rings of the picrates [centroid-to-centroid distances of 3.324 (2) Å] connect the anions to form stacks along the a-axis direction. The stacks are further joined together by the protonated water mol-ecules through hydrogen bonds to form two-dimensional sheets extending parallel to the ab plane. The sheets are stacked on top of each other along the c-axis direction and connected through C-H⋯O inter-actions between the CH groups of the benzene rings and the picrate nitro groups, with C⋯O distances of 3.450 (2) Å.

3-Carb-oxy-2-(2-cyclo-propyl-amino-4-methyl-pyridinium-3-yl-amino)-pyridinium dinitrate dihydrate.

The two benzene rings in the cation of the title compound, C(15)H(18)N(4)O(2) (2+)·2NO(3) (-)·2H(2)O, are almost perpendicular [dihedral angle = 91.6 (2)°]. In the crystal, the components are linked by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds.

Bis(1H-benzimidazol-1-yl)methane monohydrate.

In the title compound, C(15)H(12)N(4)·H(2)O, the organic mol-ecule displays approximate non-crystallographic twofold symmetry: the dihedral angle between the benzimidazole ring systems is 81.37 (12)°. In the crystal, the components are linked by O-H⋯N hydrogen bonds, forming chains propagating in [101]. Aromatic π-π stacking [centroid-centroid separation = 3.595 (2) Å] helps to consolidate the structure.

Bis[µ-bis-(diphenyl-phosphino)methane-κP:P']bis-[(2,2'-bipyridine-κN,N')copper(I)] bis-(tetra-fluoro-borate).

The centrosymmetric title compound, [Cu(2)(C(10)H(8)N(2))(2)(C(25)H(22)P(2))(2)](BF(4))(2), consists of discrete dinuclear cations and tetra-fluoro-borate anions. The two Cu(I) centers are bridged by the phosphine ligands to form an eight-membered ring. The Cu(I) center exhibits a tetra-hedral coordination as it is chelated by the N-heterocycle.

Erratum: Poly[octa-aquadi-µ-phosphato-trinickel(II)]. Corrigendum.

A correction is made to the name of the first author in Shouwen, Wang, Gao, Wen & Zhou [Acta Cryst. (2008), E64, m259].[This corrects the article DOI: 10.1107/S1600536807067050.].

Poly[µ(4)-succinato-µ(2)-succinato-bis[diamminecopper(II)]].

In the title compound, [Cu(C(4)H(4)O(4))(NH(3))(2)](n), the Cu atom is coordinated by the N atoms of two ammonia mol-ecules and four O atoms from three different succinate ligands in a highly distorted octa-hedral geometry. The Cu atom and the C and O atoms of the succinate ligands lie on a mirror plane. Two adjacent CuO(4)N(2) octa-hedra share one common O-O edge, forming a Cu(2)O(6)N(4) biocta-hedron with a Cu⋯Cu separation of 3.524 (2) Å. Neighboring biocta-hedra are connected by bis-unidentate succinate anions in the a-axis direction, while in the c-axis direction biocta-hedra are connected by bis-bidentate succinate anions, leading to an infinite two-dimensional network structure. These networks are further connected along the a-axis direction by hydrogen bonds between ammonia ligands and carboxyl-ate O atoms of neighboring network layers, forming a three-dimensional lamellar structure.

Dichloridobis(7-amino-2,4-dimethyl-1,8-naphthyridine-κN,N')cobalt(II) methanol disolvate.

The title compound, [CoCl(2)(C(10)H(11)N(3))(2)]·2CH(3)OH, crystallizes with an elongated Co coordination polyhedron in a very distorted octa-hedral geometry. Both naphthyridine ligands coordinate to the Co atom via two N atoms in a bidentate chelating mode. The remaining coordination sites are occupied by two Cl atoms. Two uncoordinated solvent methanol mol-ecules are hydrogen bonded to the Cl atoms. Additional N-H⋯O, C-H⋯Cl and N-H⋯Cl hydrogen bonds, and π-π stacking inter-actions [centroid-centroid distance 3.664 (4) Å], give rise to a three-dimensional network structure.

Bis(7-amino-2,4-dimethyl-1,8-naphthyridine)dinitratocadmium(II).

In the title compound, [Cd(NO(3))(2)(C(10)H(11)N(3))(2)], two naph-thyridine ring systems are coordinated to the Cd ion through the two N atoms in a bidentate chelating mode, whereas the remaining coordination sites are occupied by two O atoms from two different nitrate groups to complete the octahedral geometry. Inter-moleular N-H⋯O hydrogen bonds link the mol-ecules to form a one-dimensionnal sheet parallel to the ac plane. Weak slipped π-π stacking involving the naphthyridine ring systems stabilizes the structure.