Crystal structure of (nitrato-κO)bis-(1,10'-phenanthroline-κ2N,N')copper(II) nitrate gallic acid monosolvate monohydrate.

The title compound, [Cu(NO3)(C12H8N2)2]NO3·C7H6O5·H2O, consists of a mononuclear complex cation with the central CuII atom in a distorted trigonal-bipyramidal coordination sphere. Two N atoms of two 1,10-phenanthroline ligands occupy the axial sites, and the remaining N atoms of the two ligands, as well as one nitrate O atom the equatorial positions. One mol-ecule each of gallic acid and water are present in the crystal as solvent mol-ecules that do not coordinate to the CuII cation, just as the nitrate counter-anion. In the crystal, inter-molecular O-H⋯O hydrogen bonds, as well as C-H⋯O inter-actions and π-π ring stacking between benzene and pyridine rings [centroid-to-centroid distances = 3.471 (2), 3.559 (2) and 3.790 (2) Å], link the mol-ecules into a three-dimensional network structure.

Poly[[hexa-aqua-(µ(2)-oxalato-κO,O:O,O)bis(µ(3)-pyridine-2,4-dicarboxyl-ato-κN,O:O:O)dicerium(III)] monohydrate].

In the polymeric title compound, {[Ce(2)(C(7)H(3)NO(4))(2)(C(2)O(4))(H(2)O)(6)]·H(2)O}(n), the Ce(3+) cation is nine-coordinated in a distorted CeNO(8) tricapped trigonal-prismatic geometry, formed by three pyridine-2,4-dicarboxyl-ate anions, one oxalate anion and three water mol-ecules. The mid-point of the oxalate anion is located on an inversion center. The oxalate and pyridine-2,4-dicarboxyl-ate anions bridge the Ce(3+) cations, forming a two-dimensional polymeric complex parallel to (010). Inter-molecular classical O-H⋯O hydrogen bonding and weak C-H⋯O hydrogen bonding are present in the crystal structure and π-π stacking [centroid-centroid distance = 3.558 (2) Å] is observed between parallel pyridine rings of adjacent mol-ecules. The uncoordinated water mol-ecule shows an occupancy of 0.5.

Poly[[hexa-aqua-(µ(2)-oxalato-κO,O:O,O)bis-(µ(3)-pyridine-2,4-dicarboxyl-ato-κN,O:O:O)dilanthanum(III)] monohydrate].

In the polymeric title compound, {[La(2)(C(7)H(3)NO(4))(2)(C(2)O(4))(H(2)O)(6)]·H(2)O}(n), the La(3+) cation is nine-coordinated in a distorted LaNO(8) tricapped trigonal-prismatic geometry formed by three pyridinedicarboxylate anions, one oxalate anion and three water mol-ecules. The oxalate anion is located on an inversion center. The oxalate and pyridine-dicarboxyl-ate anions bridge the La(3+) cations, forming a two-dimensional polymeric complex parallel to (010). Inter-molecular O-H⋯O hydrogen bonding and weak C-H⋯O hydrogen bonding is present in the crystal structure and π-π stacking [centroid-centroid distance = 3.571 (3) Å] is observed between parallel pyridine rings of adjacent mol-ecules. The uncoordinated water molecule shows an occupancy of 0.5.

Poly[[aqua-tris-(µ(4)-benzene-1,2-dicarboxyl-ato)dilanthanum(III)] hemihydrate].

The asymmetric unit of the title coordination polymer, {[La(2)(C(8)H(4)O(4))(3)(H(2)O)]·0.5H(2)O}(n), contains two independent La(III) atoms, one of which is surrounded by eight carboxyl-ate-O atoms from six benzene-1,2-dicarboxyl-ate (BDC) anions in a bicapped trigonal-prismatic geometry. The other La(III) atom is nine-coordinated in a tricapped trigonal-prismatic geometry, formed by eight carboxyl-ate-O atoms from six BDC anions and a coordinated water mol-ecule. The BDC anions bridge the La(III) atoms, forming a two-dimensional polymeric complex parallel to (001). The crystal structure contains weak O-H⋯O and non-classical C-H⋯O hydrogen bonds. A C-H⋯π inter-action is also present in the crystal structure. The uncoordinated water molecule shows half-occupation.

Poly[[tetra-aqua-bis-(µ(3)-pyridine-2,6-dicarboxyl-ato)(µ(2)-pyridine-2,6-dicarboxyl-ato)dilanthanum(III)] dihydrate].

There are two independent La(III) cations in the polymeric title compound, {[La(2)(C(7)H(3)NO(4))(3)(H(2)O)(4)]·2H(2)O}(n). One is nine-coordinated in an LaN(2)O(7) tricapped trigonal-prismatic geometry formed by three pyridine-2,6-dicarboxyl-ate anions and two water mol-ecules, while the other is ten-coordinated in an LaNO(9) bicapped square-anti-prismatic geometry formed by four pyridine-2,6-dicarboxyl-ate anions and two water mol-ecules. The two La(III) cations are separated by a non-bonding distance of 5.026 (3) Å. The pyridine-2,6-dicarboxyl-ate anions bridge the La(III) cations, forming a three-dimensional polymeric complex. The crystal structure contains extensive classical O-H⋯O hydrogen bonds and weak inter-molecular C-H⋯O hydrogen bonds. The crystal structure is further consolidated by π-π stacking between pyridine rings, the shortest centroid-centroid distance between parallel pyridine rings being 3.700 (5) Å.

Poly[[dodeca-aqua-hexa-kis-(µ(2)-pyridine-2,5-dicarboxyl-ato)tricopper(II)diytterbium(III)] dihydrate].

The asymmetric unit of the title heterometallic coordination polymer, {[Cu(3)Yb(2)(C(7)H(3)NO(4))(6)(H(2)O)(12)]·2H(2)O}(n), contains one Yb(III) and two Cu(II) atoms. The Cu(II) atom that is located on an inversion center is N,O-chelated by two pyridine-2,5-dicarboxyl-ate (pdc) anions in a square-planar geometry; the Cu atom located on a general position is N,O-chelated by two pdc anions in the basal plane and is further coordinated by a water O atom at the apical position in a distorted square-pyramidal geometry. The Yb(III) atom is eight coordinated in a distorted square-anti-prismatic geometry formed by three carboxyl-ate O atoms from three pdc anions and five water mol-ecules. The pdc anions bridge adjacent Yb(III) and Cu(III) atoms, forming a three-dimensional polymeric structure. The crystal structure contains extensive O-H⋯O hydrogen bonds. π-π stacking is present in the crystal structure, the shortest centroid-centroid distance between parallel pyridine rings of adjacent mol-ecules being 3.646 (3) Å.

Poly[[octa-aqua-tetra-kis-(µ(3)-pyridine-2,5-dicarboxyl-ato)copper(II)diytterbium(III)] monohydrate].

The asymmetric unit of the title heterometallic polymeric coordination compound, {[CuYb(2)(C(7)H(3)NO(4))(4)(H(2)O)(8)]·H(2)O}(n), contains one Cu(II) cation located on an inversion center, a Yb(III) cation, two pyridine-2,5-dicarboxyl-ate (pda) anions, four coordination water mol-ecules a disordered lattice water molecule, which is half-occupied and is located close to an inversion center. The Cu(II) cation is N,O-chelated by two pda anions in the coordination basal plane and further coordinated by two carboxyl O atoms at the apical positions, with an elongated octa-hedral geometry. The Yb(III) atom is eight-coordinated in a distorted square-anti-prismatic geometry formed by two carboxyl-ate O atoms from two pda anions, and is N,O-chelated by one pda anion and four coordinated water mol-ecules. The pda anions bridge adjacent Yb and Cu cations, forming a three-dimensional polymeric structure. The crystal structure features extensive O-H⋯O hydrogen bonds. π-π stacking is observed between parallel pyridine rings, the centroid-centroid distance being 3.843 (4) Å.

4-Amino-3-methyl-benzoic acid-1,2-bis-(4-pyrid-yl)ethane (1/1).

In the crystal structure of the title 1:1 adduct, C(12)H(12)N(2)·C(8)H(9)NO(2), the 4-amino-3-methyl-benzoic acid mol-ecules and 1,2-bis-(4-pyrid-yl)ethane mol-ecules are linked by inter-molecular O-H⋯N, N-H⋯O and N-H⋯N hydrogen bonds, forming a two-dimensional supra-molecular network parallel to (001). In the 1,2-bis-(4-pyrid-yl)ethane mol-ecule, the two pyridine rings are twisted to each other by a dihedral angle of 12.12 (8)°. The non-H atoms of the 4-amino-3-methyl-benzoic acid mol-ecule are almost coplanar, the maximum atomic deviation being 0.029 (1) Å. Weak C-H⋯π inter-actions are present in the crystal structure.

Poly[triaqua-tris-(µ(4)-pyridine-3,5-dicarboxyl-ato)dicerium(III)].

The asymmetric unit of the title compound, [Ce(2)(C(7)H(3)NO(4))(3)(H(2)O)(3)](n), contains two Ce(III) cations, three pyridine-3,5-dicarboxyl-ate (pyd) anions and three coordinated water mol-ecules. One Ce(III) cation is coordinated by seven carboxyl-ate O atoms from six pyd anions and two water mol-ecules in a square-face-capped square-anti-prismatic geometry. Another Ce(III) cation is coordinated by seven O atoms from six pdy anions and one water mol-ecule in a bicapped trigonal-prismatic geometry. The pdy anions bridge the Ce(III) cations, forming the three-dimensional polymeric structure. The crystal structure contains extensive O-H⋯O, O-H⋯N and weak C-H⋯O hydrogen bonds. π-π stacking is present in the crystal structure, the shortest centroid-centroid distance between parallel pyridine rings being 3.509 (4) Å.

Poly[(µ(4)-pyridine-2,3-dicarboxyl-ato)lead(II)].

In the title coordination polymer, [Pb(C(7)H(3)NO(4))](n), the Pb(II) ion is eight-coordinated in a distorted square-anti-prismatic geometry formed by one pyridine N atom and seven carboxyl-ate O atoms from four pyridine-2,3-dicarboxyl-ate (pda) anions. In the pda anion, the dihedral angles between the pyridine ring and carboxyl-ate groups are 19.5 (6) and 73.3 (6)°. The carboxyl-ate groups of the pda anions bridge the Pb ions, forming a two-dimensional coordination polymer parallel to (100). Weak inter-molecular C-H⋯O hydrogen boning is present in the crystal structure.

3-Amino-benzoic acid-1,2-bis-(4-pyrid-yl)ethane (1/1).

The asymmetric unit of the title compound, C(12)H(12)N(2)·C(7)H(7)NO(2), contains two 3-amino-benzoic acid mol-ecules and two 1,2-bis-(4-pyrid-yl)ethane mol-ecules. In the two 1,2-bis-(4-pyrid-yl)ethane mol-ecules, the dihedral angles between the pyridyl rings are 2.99 (9) and 46.78 (8)°. In the crystal, the mol-ecules associate through amine and carboxyl group N-H⋯O=C inter-actions between one of the 3-amino-benzoic acid mol-ecules and one of the 1,2-bis-(4-pyrid-yl)ethane mol-ecules, generating R(2) (2)(14) dimers, which are extended head-to-tail via amine and pyridine N-H⋯N hydrogen bonds. Inter-molecular O-H⋯N, N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonding are observed in the crystal structure. C-H⋯π and π-π stacking inter-actions [centroid-centroid distance = 3.9985 (10) Å] are also present.

Tri-µ-sulfato-κO:O'-bis-[aqua-(1,10-phenanthroline-κN,N')indium(III)] dihydrate.

In the title dinuclear In(III) compound, [In(2)(SO(4))(3)(C(12)H(8)N(2))(2)(H(2)O)(2)]·2H(2)O, each In(III) cation is coordinated by a 1,10-phenanthroline (phen) ligand, a water mol-ecule and three sulfate O atoms in a distorted InN(2)O(4) octa-hedral geometry. Three sulfate anions bridge two In(III) cations, forming the dinuclear entities. O-H⋯O and weak C-H⋯O hydrogen bonding is observed in the crystal structure. The crystal structure is further consolidated by π-π stacking between nearly parallel phen ring systems [dihedral angle = 4.2 (4)°], the centroid-centroid distance between benzene rings of adjacent phen ligands being 3.528 (9) Å.

Bis(2,9-dimethyl-1,10-phenanthroline-κN,N')bis-(nitrato-κO,O')lead(II).

In the title complex, [Pb(NO(3))(2)(C(14)H(12)N(2))(2)], the lead ion is chelated by two 2,9-dimethyl-1,10-phenanthroline (dmphen) ligands and two nitrate anions in a slightly distorted square-anti-prismatic geometry. Intra- and inter-molecular π-π stacking is present in the crystal structure, and the centroid-centroid distances between the benzene and pyridine rings of adjacent dmphen ligands are 3.492 (3) and 3.592 (3) Å, respectively. Inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions help to stabilize the crystal structure.

4-Amino-benzoic acid-1,2-bis-(4-pyrid-yl)ethane (2/1).

In the title compound, C(12)H(12)N(2)·2C(7)H(7)NO(2), the 4-amino-benzoic acid mol-ecules are linked by O-H⋯N hydrogen bonds to 1,2-bis-(4-pyrid-yl)ethane, forming linear hydrogen bonded chains parallel to [21]. The structure exhibits a hydrogen-bonding network involving COOH⋯N(pyrid-yl) and amine and carb-oxy-lic N-H⋯ O inter-actions. In addition, π-π stacking inter-actions [centroid-centroid distance = 3.8622 (14) Å] are also present.

4,4'-Ethyl-enedipyridinium bis-(3,4,5-trihy-droxy-benzoate) sesquihydrate.

The asymmetric unit of the title compound, C(12)H(14)N(2) (2+)·2C(7)H(5)O(5) (-)·1.5H(2)O, contains two 4,4'-ethyl-enedipyridinium cations, four gallate anions and three water mol-ecules. In the 4,4'-ethyl-enedipyridinium cations, the dihedral angles between the pyridinium rings are 4.3 (3) and 18.6 (3)°. Extensive classical N-H⋯O and O-H⋯O hydrogen bonding and weak C-H⋯O hydrogen bonding and C-H⋯π inter-actions are present in the crystal structure. π-π stacking is also observed, the centroid-centroid separations between the benzene and pyridine rings being 3.611 (3), 3.448 (3) and 3.536 (3) Å.

Poly[(µ(3)-5-amino-isophthalato-κO,O':O'':O''')[µ(2)-1,2-bis-(4-pyrid-yl)ethane-κN:N']cobalt(II)].

In the title compound, [Co(C(8)H(5)NO(4))(C(12)H(12)N(2))](n), the Co(II) ion presents a distorted CoO(4)N(2) octa-hedral coordination geometry, formed by three 5-amino-isophthalate dianions and two 1,2-bis-(4-pyrid-yl)ethane ligands. One carboxyl-ate group of the 5-amino-isophthalate dianion chelates a Co cation and the other carboxyl-ate group bridges the other two Co cations, while the terminal N atoms of the 1,2-bis-(4-pyrid-yl)ethane ligand coordinate the neighboring Co cations, forming a two-dimensional polymeric architecture. Two pyridine rings of the 1,2-bis-(4-pyrid-yl)ethane ligand are twisted to each other with a dihedral angle of 50.94 (16)°. Weak C-H⋯O hydrogen bonding and N-H⋯π inter-actions are observed in the crystal structure. A void of 69 (5) Å(3) is present in the crystal structure, but no solvent mol-ecule can be located reasonably.

Poly[[µ(2)-1,2-bis-(4-pyrid-yl)ethene-κN:N']-di-µ(3)-bromido-dicopper(I)].

In the title polymeric Cu(I) compound, [Cu(2)Br(2)(C(12)H(10)N(2))](n), the Cu cation is coordinated by an N atom from the 1,2-bis-(4-pyrid-yl)ethene ligand and three Br(-) anions in a distorted tetra-hedral CuBr(3)N coordination geometry. Each Br(-) anion bridges three Cu cations related by inversion centers, forming a stair-like polymeric chain along the a axis, and the terminal N atoms of the 1,2-bis-(4-pyrid-yl)ethene ligand, located across an inversion center, coordinate the Cu cations from neighboring chains, forming polymeric sheets.

1,10-Phenanthrolin-1-ium nitrate-aqua-bis-(4-hydroxy-benzoato-κO,O')(nitrato-κO,O')(1,10-phenanthroline-κN,N')erbium(III)-1,10-phenanthroline-water (1/1/0.5/2).

In the title compound, C(12)H(9)N(2) (+)·NO(3) (-)·[Er(C(7)H(5)O(3))(2)(NO(3))(C(12)H(8)N(2))(H(2)O)]·0.5C(12)H(8)N(2)·2H(2)O, the water-mol-ecule-coordinated Er(III) ion is chelated by one 1,10-phenanthroline (phen) ligand, two 4-hy-droxy-benzoate anions and one nitrate anion in a monocapped square-anti-prismatic coordination geometry. The uncoordinating phen mol-ecule is approximately parallel to the 1,10-phenanthrolin-1-ium (Hphen) anion [dihedral angle = 3.3 (4)°]. The centroid-centroid distance of 3.801 (5) Šbetween pyridine rings suggests the existence of π-π stacking. The crystal structure contains an extensive network of classical O-H⋯O and N-H⋯O and weak C-H⋯O hydrogen bonds. C-H⋯π inter-actions between phen and 4-hy-droxy-benzoate is also present in the crystal structure. In the crystal, the uncoordinating phen is equally disordered over two sites about an inversion center.

catena-Poly[bis(µ(3)-3-aminobenzoato-κN:O:O,O')bis(µ(2)-3-aminobenzoato-κO,O':O)dilead(II)].

The Pb(II )atom in the title compound, {[Pb(2)(C(7)H(6)NO(2))(4)]}(n), is chelated by two 3-aminobenzoato ligands in a distorted pentagonal-bipyramidal coordination geometry with five oxygen donors in the equatorial positions, one nitro-gen donor and one oxygen donor in the axial positions. Two mol-ecules are linked through a centre of inversion, forming a dinuclear entity. These entities are linked in a µ(3)-bridging mode through the amino N atom and two carboxyl-ate O atoms into a chain along the b axis. Classical inter-molecular N-H⋯O hydrogen bonding is observed in the structure. The supra-molecular structure is consolidated by π-π stacking inter-actions with centroid-centroid distances between benzene rings of 3.837 (8) Å.

4,4'-(Ethane-1,2-diyl)dipyridinium bis-(2-hy-droxy-benzoate).

In the crystal structure of the title compound, C(12)H(14)N(2) (2+)·2C(7)H(5)O(3) (-), the cations and anions are linked via N-H⋯O hydrogen bonds and weak inter-molecular C-H⋯O inter-actions also occur. π-π stacking is observed between the nearly parallel benzene and pyridine rings [dihedral angle = 6.03 (8)°], the centroid-centroid separation being 3.7546 (16) Å. The 4,4'-(ethane-1,2-diyl)dipyridinium cation is centrosymmetric and the mid-point of the ethyl-ene C-C bond is located on an inversion center. An intra-molecular O-H⋯O hydrogen bond occurs in the anion.