Synthesis, crystal structure and Hirshfeld surface analysis of di-aqua-bis-(o-phenyl-enedi-amine-κ2N,N')nickel(II) naphthalene-1,5-di-sulfonate.

The reaction of o-phenyl-enedi-amine (OPD), sodium naphthalene1,5-di-sulfonate (Na2NDS) and nickel sulfate in an ethanol-water mixture yielded the title compound, [Ni(OPD)2(H2O)2]·NDS or [Ni(C6H8N2)2(H2O)2](C10H6O6S2). This salt consists of a complex [Ni(OPD)2(H2O)2]2+ cation with two bidentate OPD ligands and trans aqua ligands, and a non-coordinating NDS2- anion, which is the double-deprotonated form of H2NDS. The NiII atom is situated at a center of inversion and exhibits a slightly tetra-gonally distorted {O2N4} octa-hedral coordination environment, with four shorter equatorial Ni-N bonds [2.0775 (17) and 2.0924 (18) Å] and a longer axial Ni-O bond [2.1381 (17) Å]. The OPD ligand is located about an inversion center and is nearly coplanar with the NiN4 plane [dihedral angle 0.95 (9)°]. In the crystal, the cations and anions are connected by charge-assisted inter-molecular N-H⋯O and O-H⋯O hydrogen-bonding inter-actions into the tri-periodic network structure. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (44.1%), O⋯H/H⋯O (34.3%), C⋯H/H⋯C (14.8%) C⋯C (6.5%) (involving the cations) and O⋯H/H⋯O (50%), H⋯H (25%), C⋯H/H⋯C (15.3%), C⋯C (8.2%) (involving the anions) inter-actions.

Crystal structure and Hirshfeld surface analysis of 8-aza-niumylquinolinium tetra-chlorido-zincate(II).

The reaction of 8-amino-quinoline, zinc chloride and hydro-chloric acid in ethanol yielded the title salt, (C9H10N2)[ZnCl4], which consists of a planar 8-aza-n-ium-yl-quinolinium dication and a tetra-hedral tetra-chloro-zincate dianion. The 8-amino-quinoline moiety is protonated at both the amino and the ring N atoms. In the crystal, the cations and anions are connected by inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds, forming sheets parallel to (001). Adjacent sheets are linked through π-π inter-actions involving the pyridine and arene rings of the 8-aza-niumylquinolinium dication. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯Cl (48.1%), H⋯H (19.9%), H⋯C/C⋯H (14.3%) (involving the cations) and H⋯Cl (82.6%) (involving the anions) interactions.

Synthesis, crystal structure, Hirshfeld surface analysis and DFT study of the 1,1'-(buta-1,3-diyne-1,4-di-yl)bis-(cyclo-hexan-1-ol).

The title compound, C16H22O2, was synthesized in order to obtain its guest-free form because 'wheel-and-axle'-shaped mol-ecules tend to crystallize from solutions as solvates or host-guest mol-ecules. It crystallizes in the monoclinic space group P2/c with two crystallographically non-equivalent mol-ecules, one situated on an inversion center and the other on a twofold axis. The rod-like 1,3-diyne fragments have the usual linear geometry. In the crystal, O-H ⋯ O bonds form eight-membered rings of the R 4 4(8) type, linking mol-ecules into layers. The Hirshfeld surface analysis indicates that the largest con-tributions are from inter-molecular H⋯H (ca 71%) and H⋯C/C⋯H (ca 19%) contacts. The energies of the frontier mol-ecular orbitals were determined by DFT calculations at the B3LYP/def2-TZVP level of theory.

Synthesis, crystal structure and Hirshfeld surface analysis of catena-poly[[bis-(semicarbazide-κ2 N,O)copper(II)]-µ-sulfato-κ2 O:O'].

The title polymer, [Cu(SO4)(CH5N3O)2] n , has been synthesized from aqueous solutions of CuSO4 and semicarbazide. In the crystal structure, the CuII atoms are chelated by two neutral semicarbazide mol-ecules through the oxygen atom and a nitro-gen atom of the amino group. The remaining two positions of the Jahn-Teller-distorted octa-hedral coordination sphere are occupied by oxygen atoms of two sulfate anions in the axial positions. The coordination bonds of the latter associate the polyhedra into polymeric chains running parallel to the c axis. There is a weak intra-molecular hydrogen bond between the N-H group and an oxygen atom of the SO4 2- anion. Thirteen relatively weak inter-molecular hydrogen-bonding inter-actions link the chains into a three-dimensional network. Hirshfeld surface analysis revealed that 64.7% of the inter-molecular inter-actions are from O⋯H/H⋯O contacts and 20.1% from H⋯H contacts. Other inter-actions such as N⋯H/H⋯N or C⋯H/H⋯C contribute less to the crystal packing.

Crystal structure, Hirshfeld surface analysis and DFT studies of tetra-kis-(µ-3-nitro-benzoato-κ2 O 1:O 1')bis-[(N,N-di-methyl-formamide-κO)copper(II)] di-methyl-formamide disolvate.

The title compound, [Cu2(C7H4NO4)4(C3H7NO)2]·(C3H7NO)2, is a binuclear copper(II) complex located on an inversion center midway between the two copper(II) cations. The asymmetric unit consists of one CuII cation, two 3-nitro-benzoato ligands, and two di-methyl-formamide (DMF) mol-ecules, one of which coordinates to the CuII cation and one is a solvate mol-ecule. The carboxyl-ate groups of the ligands bridge two CuII cations with a Cu-Cu distance of 2.6554 (6) Å, completing a distorted octa-hedral O5Cu coordination environment. The dihedral angles between the carboxyl-ate and the aromatic ring planes of the two independent ligands are different from one another, viz. 5.2 (3) and 23.9 (3)°. The three-dimensional structure is consolidated by weak C-H⋯O inter-actions and stabilized by π-π stacking inter-actions between the aromatic rings. The complex and the free ligand were further characterized by Fourier-transform infrared spectroscopy (FT-IR), and the energies of the frontier mol-ecular orbitals of the complex were determined by DFT calculations at the B3LYP/def2-TZVP level of theory.

Crystal structure of trans-bis-[2-(1H-benzotriazol-1-yl)acetato-κO]bis-(ethano-lamine-κ2 N,O)copper(II).

The reaction of 2-(1H-benzotriazol-1-yl)acetic acid (HBTA; C8H7N3O2) and mono-ethano-lamine (MEA; C2H7NO) with CuCl2·2H2O resulted in the formation of the title complex, [Cu(C8H6N3O2)2(C2H7NO)2] or [Cu(BTA)2(MEA)2]. Its asymmetric unit comprises one BTA anion coordin-ating to the Cu2+ cation (site symmetry ) through the carboxyl O atom, and one MEA ligand chelating the metal cation by two heteroatoms (O and N). The equatorial Cu-O and Cu-N bond lengths are similar at 2.029 (1) and 1.980 (2) Å, respectively, while the length of the axial Cu-O bond is considerably greater [2.492 (2) Å], as is typical for Jahn-Teller-distorted systems. An intra-molecular hydrogen bond is present between the hy-droxy group of the MEA ligand and the non-coordinating O atom of the carboxyl-ate group. Inter-molecular hydrogen bonding involving the amino function of the MEA ligand and the carboxyl-ate group results in eight-membered rings with an R 2 2(8) graph-set motif. The mol-ecules are further linked by C-H⋯π inter-actions involving the triazole rings and methyl-ene groups of MEA, thus generating an overall three-dimensional supra-molecular framework.

Crystal structure of the salt bis-(tri-ethano-lamine-κ(3) N,O,O')cobalt(II) bis-[2-(2-oxo-2,3-di-hydro-1,3-benzo-thia-zol-3-yl)acetate].

The reaction of 2-(2-oxo-2,3-di-hydro-1,3-benzo-thia-zol-3-yl)acetic acid (NBTA) and tri-ethano-lamine (TEA) with Co(NO3)2 results in the formation of the title complex, [Co(C6H15NO3)2](C9H6NO3S)2, which is formed as a result of the association of bis-(tri-ethano-lamine)-cobalt(II) and 2-(2-oxo-2,3-di-hydro-1,3-benzo-thia-zol-3-yl)acetate units. It crystallizes in the monoclinic centrosymmetric space group P21/c, with the Co(II) ion situated on an inversion centre. In the complex cation, the Co(II) ion is octa-hedrally coordinated by two N,O,O'-tridentate TEA mol-ecules with a facial distribution and the N atoms in a trans arrangement. Two ethanol groups of each TEA mol-ecule form two five-membered chelate rings around the Co(II) ion, while the third ethanol group does not coordinate to the metal. The free and coordinating hy-droxy groups of the TEA mol-ecules are involved in hydrogen bonding with the O atoms of NBTA anions, forming an infinite two-dimensional network extending parallel to the bc plane.

Crystal structure of bis-p-anizidinegossypol with an unknown solvate.

The title compound, C44H44N2O8, (systematic name: 1,1',6,6'-tetra-hydroxy-5,5'-diisopropyl-8,8'-bis-{[(4-meth-oxy-phen-yl)iminium-yl]meth-yl}-3,3'-dimethyl-2,2'-bi-naphthalene-7,7'-diolate) has been obtained by the addition of p-anizidine to gossypol dissolved in di-chloro-methane. In the solid state, the title compound exists in the enamine or quinoid form. The two naphthyl moieties are inclined to one another by 72.08 (5)°. The pendant phenyl rings are inclined at 22.26 (14) and 23.86 (13)° to the corresponding naphthyl rings. In the crystal, mol-ecules are incorporated into layers through inversion-related pairs of O-H⋯O inter-actions [graph sets R 2 (2)(20) and R 2 (2)(10)] and translation-related O-H⋯O inter-actions [graph set C(15)]. The packing of these layers in the crystal structure gives rise to channels in the [011] direction, with hydro-phobic inter-actions occurring between adjacent layers. The channels are 5-7 Šwide, and the void volume of each cell is 655 Å(3), corresponding to 26.6% of the cell volume. Disordered guest mol-ecules, probably solvent and water mol-ecules, occupy these voids of the crystal; their contribution to the scattering was removed with the SQUEEZE routine [Spek (2015 ▸). Acta Cryst. C71, 9-18] of PLATON [Spek (2009 ▸). Acta Cryst. D65, 148-155].

Desoxyhemigossypol 6-methyl ether.

THE TITLE SESQUITERPENE [SYSTEMATIC NAME: 6-methoxy-10-methyl-7-(propan-2-yl)-2-oxatricyclo[6.3.1.0(4,12)]dodeca-1(11),4,6,8(12),9-pentaen-5-ol], C(16)H(18)O(3), was isolated from pathogen-infected stele tissue of Gossypium barbadense. There are two mol-ecules in the asymmetric unit and the dihedral angle between their naphtho-furan systems is 86.48 (2)°. In the crystal, O-H⋯O hydrogen bonds between the hy-droxy groups and etheric O atoms link the mol-ecules into centrosymmetric tetra-mers. These tetra-mers are assembled into (010) layers via stacking inter-actions between the naphtho-furan systems [inter-planar distance 3.473 (3) Å] and short C-H⋯O contacts.

2,2'-Bis{8-[(benzyl-amino)-methyl-idene]-1,6-dihy-droxy-5-isopropyl-3-methyl-naphthalen-7(8H)-one}.

The asymmetric unit of the title compound, C44H44N2O6, contains two independent mol-ecules with similar conformations. The di-hydro-naphthalene ring systems are approximately planar [maximum deviations = 0.036 (2), 0.128 (2), 0.0.24 (2) and 0.075 (2) Å]. The dihedral angle between two di-hydro-naphthalene ring systems is 83.37 (4)° in one mol-ecule and 88.99 (4)° in the other. The carbonyl O atom is linked with the adjacent hy-droxy and imino groups via intra-molecular O-H⋯O and N-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked through O-H⋯O hydrogen bonds into layers parallel to (001), and adjacent layers are further stacked by π-π inter-actions between di-hydro-naphthalene and phenyl rings into a three-dimensional supra-molecular architecture. In the crystal, one of the isopropyl groups is disordered over two positions with an occupancy ratio of 0.684 (8):0.316 (8).

Lacinilene C 7-methyl ether.

The title compound, C16H20O3 [systematic name: 1-hy-droxy-7-meth-oxy-1,6-dimethyl-4-(propan-2-yl)naphthalen-2(1H)-one], is a sesquiterpene isolated from foliar tissues of the cotton plant and is of inter-est with respect to its anti-bacterial properties. Its phenyl ring is ideally planar, and the maximum of deviation in the second ring is 0.386 (3) Å. The hy-droxy group and the methyl group are oriented in an equatorial fashion and axial, respectively, to the second ring. In the crystal, inversion dimers are formed through pairs of O-H⋯O hydrogen bonds. Weak C-H⋯O hydrogen bonds link the dimers into columns along the c axis. These columns form a crystal structure with a crystal packing factor of 0.66.

N-Cyclo-dodecyl-5-(dimethyl-amino)-naphthalene-1-sulfonamide.

The molecule of the title compound, C(24)H(36)N(2)O(2)S, displays a U-shaped conformation. The prominent inter-molecular inter-actions are N-H⋯O hydrogen bonds, resulting in the formation of dimers. Additional C-H⋯π contacts involving one of the methyl-ene groups of the macrocycle and the naphthalene rings of a neighbouring mol-ecule stabilize the packing structure. In the crystal structure, the cyclo-dodecyl ring is disordered over two positions; the site occupancy factors are ca 0.86 and 0.14.

Ethyl anthracene-9-carboxyl-ate.

In the title compound, C(17)H(14)O(2), the COO group and the anthracene fragment form a dihedral angle of 76.00 (19)°. The torsion angle around the O-Csp(3) bond of the ester group is 108.52 (18)°. The crystal structure is stabilized by C-H⋯O inter-actions and edge-to-face arene inter-actions with C-H⋯(ring centroid) distances in the range 2.75-2.84 Å.

4'-Formyl-benzo-15-crown-5.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: 17-formyl-2,5,8,11,14-penta-oxabicyclo-[13.4.0]nona-deca-15,17,19-triene), C(15)H(20)O(6), the 15-crown-5 ring adopts a twisted conformation. The formyl group is coplanar with the benzene ring. The crystal packing is stabilized by C-H⋯O inter-actions involving the C=O group and ether O atoms as acceptors and methyl-ene CH groups as donors.