The title compound, C9H7NO2, was prepared by alkynylation of 4-iodo­nitro­benzene with 1,3-dili­thio­propyne in the presence of 1 equivalent of CuI and catalytic amounts of Pd(PPh3)2Cl2. The complete mol­ecule is generated by crystallographic twofold symmetry with the C—N and C—C≡C—C units lying on the rotation axis. No directional inter­actions beyond normal van der Waals contacts could be identified in the packing.

In the title compound, [Cu2(C7HF4O2)4(C12H8N2)2(CH3OH)], the mol­ecule lies on a twofold rotation axis in space group C2/c. The Cu2+ ion exhibits a distorted octa­hedral sphere with two N atoms from the phenanthroline ligand, three O atoms from the 2,3,4,5-tetra­fluoro­benzoate ligands and one O atom from a methanol mol­ecule. The distortion from an octa­hedral shape is a consequence of the Jahn–Teller effect of CuII and the small bite angle for the bidentate fluoro­benzoate ligand [54.50 (11)°]. The methanol mol­ecule bridges two symmetry-related CuII atoms to form the complete mol­ecule. In the bidentate fluoro­benzoate ligand, one F atom is disordered over two positions of equal occupancy. In the crystal structure, only weak inter­molecular inter­actions are observed.

The structure of the title compound, [Os(C6HF4S)4{P(C6H5)3}], has been previously reported [Arroyo et al. (1994). J. Chem. Soc. Dalton Trans. pp. 1819–1824], in the space group Poverline{1}. We have now obtained a monoclinic polymorph for this compound, crystallized from ethanol, while the previous form was obtained from a hexa­ne/chloro­form mixture. The mol­ecular structure is based on a trigonal–bipyramidal OsIV coordination geometry, close to that observed previously in the triclinic form.

The crystal structure of the benzene monosolvate of the well known organic diphosphite ligand BIPHEPHOS, C46H44O8P2·C6H6, is reported for the first time. Single crystals of BIPHEPHOS were obtained from a benzene solution after layering with n-heptane at room temperature. One specific property of this type of diphosphite structure is the twisting of the biphenyl units. In the crystal, C—H⋯π contacts and π–π stacking inter­actions [centroid-to-centroid distance = 3.8941 (15) Å] are observed.

In the title hydrated salt, [Ni(C21H17F2N3)2](NO3)2·2H2O, the central NiII ion is coordinated by six N atoms from two tridentate chelating 2,6-bis­[(E)-(4-fluoro­benzyl­imino)­meth­yl]pyridine ligands. While the central NiII ion is six-coordinate, its environment is distorted from an octa­hedral structure because of the unequal Ni—N distances. The Ni—N bond lengths vary from 1.8642 (14) to 2.2131 (15) Å, while the N—Ni—N angles range from 79.98 (6) to 104.44 (6)°. Three coordinating sites of each chelating agent are almost coplanar with respect to the pyridine ring, and two pyridine moieties are perpendicular to each other. Two non-coordinating nitrate anions within the asymmetric unit balance the charges of the central metal ion, and are linked with two crystal water mol­ecules, forming a water–nitrate cyclic tetra­meric unit [O⋯O = 2.813 (2) to 3.062 (2) Å]. In an isolated mol­ecule, the fluoro­phenyl rings of one ligand are stacked with the central ring of the other ligand via π–π inter­actions, with the closest centroid-to-plane distances being 3.359 (6), 3.408 (5), 3.757 (6) and 3.659 (5) Å.

In the title hydrated Schiff base, C13H12N4O3·H2O, the dihedral angle between the aromatic rings is 5.06 (11)° and an intra­molecular O—H⋯N hydrogen bond closes an S(6) ring. In the crystal, Ow—H⋯O and Ow—H⋯N (w = water) hydrogen bonds link the components into centrosymmetric tetra­mers (two Schiff bases and two water mol­ecules). Longer N—H⋯O hydrogen bonds link the tetra­mers into [010] chains. A weak C—H⋯O hydrogen bond and aromatic π–π stacking between the pyrazine and phenyl rings [centroid–centroid separations = 3.604 (2) and 3.715 (2) Å] are also observed.

In the title complex, [NiCl2(C12H9N3)2]·H2O, a divalent nickel atom is coordinated by two 2-(pyridin-2-yl)-1H-benzimidazole ligands in a slightly distorted octa­hedral environment defined by four N donors of two N,N'-chelating ligands, along with two cis-oriented anionic chloride donors. The title complex crystallized with a water mol­ecule disordered over two positions. In the crystal, a combination of O—H⋯Cl, O—H.·O and N—H⋯Cl hydrogen bonds, together with C—H⋯O, C—H⋯Cl and C—H⋯π inter­actions, links the complex mol­ecules and the water mol­ecules to form a supra­molecular three-dimensional framework. The title complex is isostructural with the cobalt(II) dichloride complex reported previously [Das et al. (2011). Org. Biomol. Chem. 9, 7097–7107].

The structure of the title salt, C6H10N22+·2C7H7O3S−, consists of a unique benzene-1,2-diaminium dication charge balanced by a pair of crystallographically independent 4-methyl­benzene-1-sulfonate anions. The cations and anions are inter­linked by several N—H⋯O hydrogen bonds.

In the title compound, C19H13IO2, the dihedral angle between the naphthyl ring system and the pendant iodo­phenyl ring is 72.48 (11)°. In the crystal, C—H⋯π inter­actions and I⋯O [3.293 (2) Å] halogen bonds are observed, which combine to generate a herringbone packing motif.

In the extended structure of the title mol­ecular salt, C6H9N2+·C7H7O3S−, the cations and anions are linked by N—H⋯O hydrogen bonds to generate [010] chains.

The relative stereo- and regiochemistry of the racemic title compound, C25H19NO7, were established from the crystal structure. The fused benzene ring forms dihedral angles of 77.3 (1) and 60.3 (1)° with the hy­droxy-substituted benzene ring and the nitro-substituted benzene ring, respectively. The dihedral angle between the hy­droxy-substituted benzene ring and the nitro-substituted benzene ring is 76.4 (1)°. An intra­molecular O—H⋯O hydrogen bond closes an S(6) ring. In the crystal, weak C—H⋯O hydrogen bonds connect the mol­ecules, forming layers parallel to (100). Within these layers, there are weak π–π stacking inter­actions with a ring centroid–ring centroid distance of 3.555 (1) Å.

The structure of the tertiary amine tris­(1H-benzimidazol-2-ylmeth­yl)amine (C24H21N7, abbreviated ntb) has been previously reported twice as solvates, namely the monohydrate and the aceto­nitrile–methanol–water (1/0.5/1.5) solvate, both with the tripodal conformation formed via multiple hydrogen bonds. Now, we report the tri­methanol adduct, ntb·3CH3OH, where the amine has the stair conformation featuring one benzimidazole group oriented in the opposite direction from the other two. The asymmetric unit contains one-half amine, completed through the mirror plane m in space group Pmn21 to form the ntb mol­ecule, with the H atom for each imidazole moiety equally disordered between both N sites available in the imidazole ring. The asymmetric unit also contains one and a half methanol mol­ecules, one being placed in general position with the hy­droxy H atom disordered over two sites with occupancy ratio 1:1, while the other lies on the m mirror plane, and has thus its hy­droxy H atom disordered by symmetry. As in the previously reported solvates, all imine and amine groups of the ntb mol­ecules and the methanol mol­ecules are involved in N—H⋯O and O—H⋯N hydrogen bonds. In the title compound, however, the involved H atom is systematically a disordered H atom provided by an imidazole group or a methanol mol­ecule.

In the title compound, C14H11ClN2O2S, the dihedral angle between the pyrrolo­[1,2-c]pyrimidine ring system (r.m.s. deviation = 0.008 Å) and the benzene ring is 80.2 (9)°. In the crystal, inversion dimers linked by pairs of C—H⋯O inter­actions generate R22(16) loops. Several aromatic π–π stacking inter­actions between the pyrrolo­[1,2-c]pyrimidine rings, as well as separately between the pyrrolo and pyrimidine groups [shortest centroid–centroid separation = 3.5758 (14) Å], help to consolidate the packing.

The title compound, C26H22O6, is formed as the major product from the reaction between syn-1,2-bis­(pinacolatoboron)-1,2-bis­(4-methyl­carb­oxy­phen­yl)ethene and excess methyl 4-iodo­benzoate in basic DMSO using a palladium catalyst at 80°C via Suzuki coupling followed by protodeboronation. Crystals were grown by slow evaporation of a hexa­nes solution at room temperature.

The asymmetric unit of the binuclear title compound, [Cu2(C8H7O3)4(H2O)2], comprises two halves of diaquatetra­kis­(μ-3-meth­oxy­benzoato-κ2O1:O1')dicopper(II) units. The paddle-wheel structure of each complex is completed by application of inversion symmetry, with the inversion centre situated at the midpoint between two CuII atoms in each dimer. The two CuII atoms of each centrosymmetric dimer are bridged by four 3-meth­oxy­benzoate anions resulting in Cu⋯Cu separations of 2.5961 (11) and 2.6060 (12) Å, respectively. The square-pyramidal coordination sphere of each CuII atom is completed by an apical water mol­ecule. Inter­molecular O—H⋯O hydrogen bonds of weak nature link the complexes into layers parallel to (100). The three-dimensional network structure is accomplished by C—H⋯O hydrogen bonds inter­linking adjacent layers.

The title compound, C16H16N2, was synthesized by dispersing 3,4-hexa­nedione in a methanol–water solution containing the acid catalyst NH4HF2, then adding 1,2-di­aminona­phthalene. The fused-ring system of the title compound is close to planar (r.m.s. deviation = 0.028 Å); one of the pendant methyl C atoms lies close to the ring plane [deviation = 0.071 (2) Å; N—C—C—C = −0.27 (18)°] whereas the other is significantly displaced [–1.7136 (18) Å; 91.64 (16)°]. The mol­ecules pack in space group Ioverline{4} in a distinctive criss-cross motif supported by numerous aromatic π–π stacking inter­actions [shortest centroid–centroid separation = 3.5805 (6) Å].

This work presents the synthesis and structural characterization of [4-(1H-benzo[d]imidazol-2-yl)phen­oxy]phthalo­nitrile, a phthalo­nitrile derivative carrying a benzimidazole moiety. The compound crystallizes as its dimethyl sulfoxide monosolvate, C21H12N4O·(CH3)2SO. The dihedral angle between the two fused rings in the heterocyclic ring system is 2.11 (1)°, while the phenyl ring attached to the imidazole moiety is inclined by 20.7 (1)° to the latter. In the crystal structure, adjacent mol­ecules are connected by pairs of weak inter­molecular C—H⋯N hydrogen bonds into inversion dimers. N—H⋯O and C—H⋯O hydrogen bonds with R21(7) graph-set motifs are also formed between the organic mol­ecule and the disordered dimethyl sulfoxide solvent [occupancy ratio of 0.623 (5):0.377 (5) for the two sites of the sulfur atom]. Hirshfeld surface analysis and fingerprint plots were used to investigate the inter­molecular inter­actions in the crystalline state.

The mol­ecule of the title Schiff base compound, C14H13N3O3·H2O, displays a trans configuration with respect to the C=N bond. The dihedral angle between the benzene and pyridine rings is 29.63 (7)°. The crystal structure features inter­molecular N—H⋯O, C—H⋯O, O—H⋯O and O—H⋯N hydrogen-bonding inter­actions, leading to the formation of a supramolecular framework. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (37.0%), O⋯H/H⋯O (23.7%)), C⋯H/H⋯C (17.6%) and N⋯H/H⋯N (11.9%) inter­actions. The title compound has also been characterized by frontier mol­ecular orbital analysis.

The title compounds, C24H22O6 (I) and C24H22O6 (II), each crystallize with half a mol­ecule in the asymmetric unit. The whole mol­ecule of compound (I) is generated by twofold rotation symmetry, the twofold axis bis­ecting the central benzene ring. The whole mol­ecule of compound (II) is generated by inversion symmetry, the central benzene ring being located on an inversion center. In (I), the outer benzene rings are inclined to each other by 59.96 (10)° and by 36.74 (9)° to the central benzene ring. The corresponding dihedral angles in (II) are 0.0 and 89.87 (12)°. In the crystal of (I), mol­ecules are linked by C—H⋯O hydrogen bonds and C—H⋯π inter­actions, forming ribbons propagating along the [10overline{1}] direction. In the crystal of (II), mol­ecules are linked by C—H⋯O hydrogen bonds, forming a supra­molecular framework. The Hirshfeld surface analyses indicate that for both compounds the H⋯H contacts are the most significant, followed by O⋯H/H⋯O and C⋯H/H⋯C contacts.

The title binuclear CoIII complex, [Co2(C9H8BrNOS)2(C18H16Br2N2O2S2)]·C3H7NO, with a Schiff base ligand formed in situ from cyste­amine (2-amino­ethane­thiol) and 5-bromo­salicyl­aldehyde crystallizes in the space group P21. It was found that during the synthesis the ligand undergoes spontaneous oxidation, forming the new ligand H2L' having an S—S bond. Thus, the asymmetric unit consists of one Co2(L)2(L') mol­ecule and one DMF solvent mol­ecule. Each CoIII ion has a slightly distorted octa­hedral S2N2O2 coordination geometry. In the crystal, the components are linked into a three-dimensional network by several S⋯ Br, C⋯ Br, C—H⋯Br, short S⋯C (essentially shorter than the sum of the van der Waals radii for the atoms involved) contacts as well by weak C—H⋯O hydrogen bonds. The crystal studied was refined as an inversion twin.

The title benzo­furan derivatives 2-amino-5-hy­droxy-4-(4-nitro­phen­yl)benzo­furan-3-carboxyl­ate (BF1), C19H18N2O6, and 2-meth­oxy­ethyl 2-amino-5-hy­droxy-4-(4-nitro­phen­yl)benzo­furan-3-carboxyl­ate (BF2), C18H16N2O7, recently attracted attention because of their promising anti­tumoral activity. BF1 crystallizes in the space group Poverline{1}. BF2 in the space group P21/c. The nitro­phenyl group is inclined to benzo­furan moiety with a dihedral angle between their mean planes of 69.2 (2)° in BF1 and 60.20 (6)° in BF2. A common feature in the mol­ecular structures of BF1 and BF2 is the intra­molecular N—H⋯Ocarbon­yl hydrogen bond. In the crystal of BF1, the mol­ecules are linked head-to-tail into a one-dimensional hydrogen-bonding pattern along the a-axis direction. In BF2, pairs of head-to-tail hydrogen-bonded chains of mol­ecules along the b-axis direction are linked by O—H⋯Ometh­oxy hydrogen bonds. In BF1, the butyl group is disordered over two orientations with occupancies of 0.557 (13) and 0.443 (13).

The title pyridazinone derivative, C21H19ClN2O3, is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°]. In the crystal, C—H⋯O hydrogen bonds generate dimers with R22(10) and R22(24) ring motifs which are linked by C—H⋯O inter­actions, forming chains extending parallel to the c-axis direction. The inter­molecular inter­actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most significant contributions to the crystal packing are from H⋯H (44.5%), C⋯H/H⋯C (18.5%), H⋯O/H⋯O (15.6%), Cl⋯H/H⋯Cl (10.6%) and C⋯C (2.8%) contacts.

The asymmetric unit of the title compound, [Ni(C52H34Cl4N4O4)]·CH2Cl2, consists of two discrete complexes, which show significant differences in the conformation of the side chain. Each NiII cation is coordinated by four nitro­gen atoms of a porphyrin mol­ecule within a square-planar coordination environment. Weak intra­molecular C—H⋯Cl and C—H⋯O inter­actions stabilize the mol­ecular conformation. In the crystal structure, discrete complexes are linked by C—H⋯Cl hydrogen-bonding inter­actions. In addition, the two unique di­chloro­methane solvate mol­ecules (one being disordered) are hydrogen-bonded to the Cl atoms of the chloro­phenyl groups of the porphyrin mol­ecules, thus stabilizing the three-dimensional arrangement. The crystal exhibits pseudo-ortho­rhom­bic metrics, but structure refinements clearly show that the crystal system is monoclinic and that the crystal is twinned by pseudo-merohedry.

In the title compound, C20H18NO3P, the C=O and P=O groups of the carbacyl­amido­phosphate (CAPh) fragments are located in a synclinal position relative to each other and are pre-organized for bidentate chelate coordination of metal ions. The N—H group is involved in the formation of an intra­molecular hydrogen bond. In the crystal, mol­ecules do not form strong inter­molecular inter­actions but the mol­ecules are linked via weak C—H⋯π inter­actions, forming chains along [001].

The asymmetric unit of the title compound, [Fe(NCS)2(C12H9NO)4], consists of an FeII ion that is located on a centre of inversion, as well as two 4-benzoyl­pyridine ligands and one thio­cyanate anion in general positions. The FeII ions are coordinated by two N-terminal-bonded thio­cyanate anions and four 4-benzoyl­pyridine ligands into discrete complexes with a slightly distorted octa­hedral geometry. These complexes are further linked by weak C—H⋯O hydrogen bonds into chains running along the c-axis direction. Upon heating, this complex loses half of the 4-benzoyl­pyridine ligands and transforms into a compound with the composition Fe(NCS)2(4-benzoyl­pyridine)2, that might be isotypic to the corresponding MnII compound and for which the structure is unknown.

In the title compound, the asymmetric unit comprises an N,N,N-trimethyl-1-(4-vinyl­phen­yl)methanaminium cation and a 4-vinyl­benzene­sulfonate anion, C12H18N+·C8H7O3S−. The salt has a polymerizable vinyl group attached to both the cation and the anion. The methanaminium and vinyl substituents on the benzene ring of the cation subtend angles of 86.6 (3) and 10.5 (9)° to the ring plane, while the anion is planar excluding the sulfonate O atoms. The vinyl substituent on the benzene ring of the cation is disordered over two sites with a refined occupancy ratio of 0.542 (11):0.458 (11). In the crystal, C—H⋯O hydrogen bonds dominate the packing and combine with a C—H⋯π(ring) contact to stack the cations and anions along the a-axis direction. Hirshfeld surface analysis of the salt and of the individual cation and anion components is also reported.

In the title quinoline derivative, C24H19NO3, the two benzyl rings are inclined to the quinoline ring mean plane by 74.09 (8) and 89.43 (7)°, and to each other by 63.97 (10)°. The carboxyl­ate group is twisted from the quinoline ring mean plane by 32.2 (2)°. There is a short intra­molecular C—H⋯O contact forming an S(6) ring motif. In the crystal, mol­ecules are linked by bifurcated C—H,H⋯O hydrogen bonds, forming layers parallel to the ac plane. The layers are linked by C—H⋯π inter­actions, forming a supra­molecular three-dimensional structure.

The asymmetric unit of the title compound, C15H12N2O2, contains two crystallographically independent mol­ecules in which the dihedral angles between the benzene rings in each are 13.26 (5) and 7.87 (5)°. An intra­molecular O—H⋯N hydrogen bonds results in the formation of an S(6) ring motif. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯N hydrogen bonds, forming layers parallel to (011). In addition, π–π stacking inter­actions with centroid–centroid distances in the range 3.693 (2)–3.931 (2) Å complete the three-dimensional network.

The structures of two isomers of the title compound, [RuCl2(C14H12N4)(C2H6OS)2], 2 and 3, are reported. Isomers 2 and 3 are produced by reaction of the pyridyl­triazole ligand 1-benzyl-4-(pyridin-2-yl)-1H-1,2,3-triazole (bpt) (1) with fac-[RuCl2(DMSO-S)3(DMSO-O)]. Reaction in acetone produces ca 95% 2, which is the OC-6-14 isomer, with cis DMSO and trans chlorido ligands, and 5% 3 (the OC-6-32 isomer, with cis DMSO and cis chlorido ligands, and the pyridyl moiety of bpt trans to DMSO). Reaction in refluxing toluene initially forms 2, which slowly isomerizes to 3.

The asymmetric units of the title compounds, trans-di­aqua­(3-benzyl-1,3,5,8,12-penta­aza­cyclo­tetra­decane-κ4N1,N5,N8,N12)copper(II) isophthalate monohydrate, [Cu(C16H29N5)(H2O)2](C8H4O4)·H2O, (I), and trans-di­aqua­[3-(pyridin-3-ylmeth­yl)-1,3,5,8,12-penta­aza­cyclo­tetra­decane-κ4N1,N5,N8,N12]copper(II) iso­phthalate 0.9-hydrate, [Cu(C15H28N6)(H2O)2](C8H4O4)·0.9H2O, (II) consist of one di­aqua macrocyclic cation, one di­carboxyl­ate anion and uncoordinated water mol­ecule(s). In each compound, the metal ion is coordinated by the four secondary N atoms of the macrocyclic ligand and the mutually trans O atoms of the water mol­ecules in a tetra­gonally distorted octa­hedral geometry. The average equatorial Cu—N bond lengths are significantly shorter than the average axial Cu—O bond lengths [2.020 (9) versus 2.495 (12) Å and 2.015 (4) versus 2.507 (7) Å for (I) and (II), respectively]. The coordinated macrocyclic ligand in the cations of both compounds adopts the most energetically favorable trans-III conformation. In the crystals, the complex cations and counter-anions are connected via hydrogen-bonding inter­actions between the N—H groups of the macrocycles and the O—H groups of coordinated water mol­ecules as the proton donors and the O atoms of the carboxyl­ate as the proton acceptors. Additionally, as a result of O—H⋯O hydrogen bonding with the coordinated and water mol­ecules of crystallization, the isophthalate dianions form layers lying parallel to the (overline{1}01) and (100) planes in (I) and (II), respectively.

The title pyridazin-3(2H)-one derivative, C25H19FN2O2, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. In mol­ecule A, the 4-fluoro­phenyl ring, the benzyl ring and the phenyl ring are inclined to the central pyridazine ring by 86.54 (11), 3.70 (9) and 84.857 (13)°, respectively. In mol­ecule B, the corresponding dihedral angles are 86.80 (9), 10.47 (8) and 82.01 (10)°, respectively. In the crystal, the A mol­ecules are linked by pairs of C—H⋯F hydrogen bonds, forming inversion dimers with an R22(28) ring motif. The dimers are linked by C—H⋯O hydrogen bonds and a C—H⋯π inter­action, forming columns stacking along the a-axis direction. The B mol­ecules are linked to each other in a similar manner and form columns separating the columns of A mol­ecules.

The title compounds, C14H10ClFN2OS (1) and C14H10BrFN2OS (2), were synthesized by two-step reactions. The dihedral angles between the aromatic rings are 31.99 (3) and 9.17 (5)° for 1 and 2, respectively. Compound 1 features an intra­molecular bifurcated N—H⋯(O,Cl) link due to the presence of the ortho-Cl atom on the benzene ring, whereas 2 features an intra­molecular N—H⋯O hydrogen bond. In the crystal of 1, inversion dimers linked by pairs of N—H⋯S hydrogen bonds generate R22(8) loops. The extended structure of 2 features the same motif but an additional weak C—H⋯S inter­action links the inversion dimers into [100] double columns. Hirshfeld surface analyses indicate that the most important contributors towards the crystal packing are H⋯H (26.6%), S⋯H/H.·S (13.8%) and Cl⋯H/H⋯Cl (9.5%) contacts for 1 and H⋯H (19.7%), C⋯H/H⋯C (14.8%) and Br⋯H/H⋯Br (12.4%) contacts for 2.

The title mol­ecule crystallizes as a di­methyl­formamide monosolvate, C19H14N2O6S2·C3H7NO. The mol­ecule was expected to adopt mirror symmetry but slightly different conformational characteristics of the condensed benzo­thia­zine ring lead to point group symmetry 1. In the crystal, mol­ecules form two types of stacking dimers with distances of 3.464 (2) Å and 3.528 (2) Å between π-systems. As a result, columns extending parallel to [100] are formed, which are connected to inter­mediate di­methyl­formamide solvent mol­ecules by C—H⋯O inter­actions.

The synthesis, spectroscopic data, crystal and mol­ecular structures of two N'-(1-phenyl­benzyl­idene)-2-(thio­phen-3-yl)acetohydrazides, namely N'-[1-(4-hy­droxy­phen­yl)benzyl­idene]-2-(thio­phen-3-yl)acetohydrazide, C13H10N2O2S, (3a), and N'-[1-(4-meth­oxy­phen­yl)benzyl­idene]-2-(thio­phen-3-yl)acetohydrazide, C14H14N2O2S, (3b), are described. Both compounds differ in the substituent at the para position of the phenyl ring: –OH for (3a) and –OCH3 for (3b). In (3a), the thio­phene ring is disordered over two orientations with occupancies of 0.762 (3) and 0.238 (3). The configuration about the C=N bond is E. The thio­phene and phenyl rings are inclined by 84.0 (3) and 87.0 (9)° for the major- and minor-occupancy disorder components in (3a), and by 85.89 (12)° in (3b). Although these dihedral angles are similar, the conformation of the linker between the two rings is different [the C—C—C—N torsion angle is −ac for (3a) and −sc for (3b), while the C6—C7—N9—N10 torsion angle is +ap for (3a) and −sp for (3b)]. A common feature in the crystal packing of (3a) and (3b) is the presence of N—H⋯O hydrogen bonds, resulting in the formation of chains of mol­ecules running along the b-axis direction in the case of (3a), or inversion dimers for (3b). The most prominent contributions to the surface contacts are those in which H atoms are involved, as confirmed by an analysis of the Hirshfeld surface.

The asymmetric unit of the title compound, C15H21N3OS, comprises of two crystallographically independent mol­ecules (A and B). Each mol­ecule consists of a cyclo­hexane ring and a 2-hy­droxy-3-methyl­benzyl­idene ring bridged by a hydrazinecarbo­thio­amine unit. Both mol­ecules exhibit an E configuration with respect to the azomethine C=N bond. There is an intra­molecular O—H⋯N hydrogen bond in each mol­ecule forming an S(6) ring motif. The cyclo­hexane ring in each mol­ecule has a chair conformation. The benzene ring is inclined to the mean plane of the cyclo­hexane ring by 47.75 (9)° in mol­ecule A and 66.99 (9)° in mol­ecule B. The mean plane of the cyclo­hexane ring is inclined to the mean plane of the thio­urea moiety [N—C(=S)—N] by 55.69 (9) and 58.50 (8)° in mol­ecules A and B, respectively. In the crystal, the A and B mol­ecules are linked by N—H⋯S hydrogen bonds, forming `dimers'. The A mol­ecules are further linked by a C—H⋯π inter­action, hence linking the A–B units to form ribbons propagating along the b-axis direction. The conformation of a number of related cyclo­hexa­nehydrazinecarbo­thio­amides are compared to that of the title compound.

The asymmetric unit of the title 1:1 solvate, C14H14N4O2·C6H6 [systematic name of the oxalamide mol­ecule: N,N'-bis­(pyridin-4-ylmeth­yl)ethanedi­amide], comprises a half mol­ecule of each constituent as each is disposed about a centre of inversion. In the oxalamide mol­ecule, the central C2N2O2 atoms are planar (r.m.s. deviation = 0.0006 Å). An intra­molecular amide-N—H⋯O(amide) hydrogen bond is evident, which gives rise to an S(5) loop. Overall, the mol­ecule adopts an anti­periplanar disposition of the pyridyl rings, and an orthogonal relationship is evident between the central plane and each terminal pyridyl ring [dihedral angle = 86.89 (3)°]. In the crystal, supra­molecular layers parallel to (10overline{2}) are generated owing the formation of amide-N—H⋯N(pyrid­yl) hydrogen bonds. The layers stack encompassing benzene mol­ecules which provide the links between layers via methyl­ene-C—H⋯π(benzene) and benzene-C—H⋯π(pyrid­yl) inter­actions. The specified contacts are indicated in an analysis of the calculated Hirshfeld surfaces. The energy of stabilization provided by the conventional hydrogen bonding (approximately 40 kJ mol−1; electrostatic forces) is just over double that by the C—H⋯π contacts (dispersion forces).

In the title compound, C16H11Cl2N3O, the 4-meth­oxy-substituted benzene ring makes a dihedral angle of 41.86 (9)° with the benzene ring of the benzo­nitrile group. In the crystal, mol­ecules are linked into layers parallel to (020) by C—H⋯O contacts and face-to-face π–π stacking inter­actions [centroid–centroid distances = 3.9116 (14) and 3.9118 (14) Å] between symmetry-related aromatic rings along the a-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from Cl⋯H/H⋯Cl (22.8%), H⋯H (21.4%), N⋯H/H⋯N (16.1%), C⋯H/H⋯C (14.7%) and C⋯C (9.1%) inter­actions.

The title salt, C16H15ClN3S+·Br−, is isotypic with (E)-3-[(4-fluoro­benzyl­idene)amino]-5-phenyl­thia­zolidin-2-iminium bromide [Khalilov et al. (2019). Acta Cryst. E75, 662–666]. In the cation of the title salt, the atoms of the phenyl ring attached to the central thia­zolidine ring and the atom joining the thia­zolidine ring to the benzene ring are disordered over two sets of sites with occupancies of 0.570 (3) and 0.430 (3). The major and minor components of the disordered thia­zolidine ring adopt slightly distorted envelope conformations, with the C atom bearing the phenyl ring as the flap atom. In the crystal, centrosymmetrically related cations and anions are linked into dimeric units via N—H⋯Br hydrogen bonds, which are further connected by weak C—H⋯Br contacts into chains parallel to the a axis. Furthermore, not existing in the earlier report of (E)-3-[(4-fluoro­benzyl­idene)amino]-5-phenyl­thia­zolidin-2-iminium bromide, C—H⋯π inter­actions and π–π stacking inter­actions [centroid-to-centroid distance = 3.897 (2) Å] between the major components of the disordered phenyl ring contribute to the stabilization of the mol­ecular packing. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions for the crystal packing are from H⋯H (30.5%), Br⋯H/H⋯Br (21.2%), C⋯H/H⋯C (19.2%), Cl⋯H/H⋯Cl (13.0%) and S⋯H/H⋯S (5.0%) inter­actions.

In the title benzohydrazide derivative, C14H12N2O4, the azomethine C=N double bond has an E configuration. The hydrazide connecting bridge, (C=O)—(NH)—N=(CH), is nearly planar with C—C—N—N and C—N—N=C torsion angles of −177.33 (10) and −174.98 (12)°, respectively. The 4-hy­droxy­phenyl and 3,4-di­hydroxy­phenyl rings are slightly twisted, making a dihedral angle of 9.18 (6)°. In the crystal, mol­ecules are connected by N—H⋯O and O—H⋯O hydrogen bonds into a three-dimensional network, while further consolidated via π–π inter­actions [centroid–centroid distances = 3.6480 (8) and 3.7607 (8) Å]. The conformation is compared to those of related benzyl­idene-4-hy­droxy­benzohydrazide derivatives.

A new mononuclear NiII complex with bis­(pyridin-2-yl)amine (dpyam) and benzoate (benz), [Ni(C7H5O2)2(C10H9N3)], crystallizes in the monoclinic space group P21/c. The NiII ion adopts a cis-distorted octa­hedral geometry with an [NiN2O4] chromophore. In the crystal, the complex mol­ecules are linked together into a one-dimensional chain by symmetry-related π–π stacking inter­actions [centroid-to-centroid distance = 3.7257 (17) Å], along with N—H⋯O and C—H⋯O hydrogen bonds. The crystal packing is further stabilized by C—H⋯π inter­actions, which were investigated by Hirshfeld surface analysis.

The structure of the title compound, C32H51NO6, was determined from 62-year-old crystals at room temperature and refined with 100 K data in a monoclinic (C2) space group. This compound with a triterpenoid structure, now confirmed by this study, played an important role in the determination of the structure of lanosterol. The mol­ecules pack in linear O—H⋯O hydrogen-bonded chains along the short axis (b), while parallel chains display weak van der Waals inter­actions that explain the needle-shaped crystal morphology. The structure exhibits disorder of the flexible methyl­heptane chain at one end of the main mol­ecule with a small void around it. Crystals of the compounds were resistant to data collection for decades with the available cameras and Mo Kα radiation single-crystal diffractometer in our laboratory until a new instrument with Cu Kα radiation operating at 100 K allowed the structure to be solved and refined.

1-(2-Iodo­benzo­yl)-cyclo­pent-3-ene-1-carboxyl­ates are novel substrates to construct bi­cyclo­[3.2.1]octa­nes with anti­bacterial and anti­thrombotic activities. In this context, tert-butyl 1-(2-iodo­benzo­yl)-cyclo­pent-3-ene-1-carboxyl­ate, C17H19IO3, was synthesized and structurally characterized. The 2-iodo­benzoyl group is attached to the tertiary C atom of the cyclo­pent-3-ene ring. The dihedral angle between the benzene ring and the mean plane of the envelope-type cyclo­pent-3-ene ring is 26.0 (3)°. In the crystal, pairs of C-H⋯O hydrogen bonds link the mol­ecules to form inversion dimers.

In this paper, we describe the synthesis of a new di­hydro-2H-pyridazin-3-one derivative. The mol­ecule, C18H16N2O, is not planar; the benzene and pyridazine rings are twisted with respect to each other, making a dihedral angle of 11.47 (2)°, and the toluene ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 89.624 (1)°. The mol­ecular conformation is stabilized by weak intra­molecular C—H⋯N contacts. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with an R22(8) ring motif. The inter­molecular inter­actions were investigated using Hirshfeld surface analysis and two-dimensional (2D) fingerprint plots, revealing that the most important contributions for the crystal packing are from H⋯H (56.6%), H⋯C/C⋯H (22.6%), O⋯H/H⋯O (10.0%) and N⋯C/C⋯N (3.5%) inter­actions.

The crystal structures of the disordered hemi-DMSO solvate of (E)-2-oxo-N'-(3,4,5-tri­meth­oxy­benzyl­idene)-2H-chromene-3-carbohydrazide, C20H18N2O6·0.5C2H6OS, and (E)-N'-benzyl­idene-2-oxo-2H-chromene-3-carbohydrazide, C17H12N2O3 (4: R = C6H5), are discussed. The non-hydrogen atoms in compound [4: R = (3,4,5-MeO)3C6H2)] exhibit a distinct curvature, while those in compound, (4: R = C6H5), are essential coplanar. In (4: R = C6H5), C—H⋯O and π–π intra­molecular inter­actions combine to form a three-dimensional array. A three-dimensional array is also found for the hemi-DMSO solvate of [4: R = (3,4,5-MeO)3C6H2], in which the mol­ecules of coumarin are linked by C—H⋯O and C—H⋯π inter­actions, and form tubes into which the DMSO mol­ecules are cocooned. Hirshfeld surface analyses of both compounds are reported, as are the lattice energy and inter­molecular inter­action energy calculations of compound (4: R = C6H5).

In the title compound, C25H12Cl6O4, the two carbonyl groups are oriented in a same direction with respect to the naphthalene ring system and are situated roughly parallel to each other, while the two 2,4,6-tri­chloro­benzene rings are orientated in opposite directions with respect to the naphthalene ring system: the carbonyl C—(C=O)—C planes subtend dihedral angles of 45.54 (15) and 30.02 (15)° to the naphthalene ring system are. The dihedral angles formed by the carbonyl groups and the benzene rings show larger differences, the C=O vectors being inclined to the benzene rings by 46.39 (16) and 79.78 (16)°. An intra­molecular O—H⋯O=C hydrogen bond forms an S(6) ring motif. In the crystal, no effective inter­molecular hydrogen bonds are found; instead, O⋯Cl and C⋯Cl close contacts are observed along the 21 helical-axis direction. The Hirshfeld surface analysis reveals several weak interactions, the major contributor being Cl⋯H/H⋯Cl contacts.

The title Schiff base compound, C14H10Cl2N2O, features an E configuration about each of the C=N imine bonds. Overall, the mol­ecule is approximately planar with the dihedral angle between the central C2N2 residue (r.m.s. deviation = 0.0371 Å) and the peripheral hy­droxy­benzene and chloro­benzene rings being 4.9 (3) and 7.5 (3)°, respectively. Nevertheless, a small twist is evident about the central N—N bond [the C—N—N—C torsion angle = −172.7 (2)°]. An intra­molecular hy­droxy-O—H⋯N(imine) hydrogen bond closes an S(6) loop. In the crystal, π–π stacking inter­actions between hy­droxy- and chloro­benzene rings [inter-centroid separation = 3.6939 (13) Å] lead to a helical supra­molecular chain propagating along the b-axis direction; the chains pack without directional inter­actions between them. The calculated Hirshfeld surfaces point to the importance of H⋯H and Cl⋯H/H⋯Cl contacts to the overall surface, each contributing approximately 29% of all contacts. However, of these only Cl⋯H contacts occur at separations less than the sum of the van der Waals radii. The aforementioned π–π stacking inter­actions contribute 12.0% to the overall surface contacts. The calculation of the inter­action energies in the crystal indicates significant contributions from the dispersion term.

In the title compound, [Cd(NO3)2(C13H11N3)2], the CdII atom lies on a twofold rotation axis and is coordinated by four N atoms and two O atoms, provided by two bidentate 2-(1H-benzimidazol-2-yl)aniline ligands, and two nitrato O atoms, forming a distorted octa­hedral geometry [range of bond angles around the Cd atom = 73.82 (2)–106.95 (8)°]. In the ligand, the dihedral angle between the aniline ring and the benzimidazole ring system is 30.43 (7)°. The discrete complex mol­ecule is stabilized by an intra­molecular N—H⋯O hydrogen bond. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules, forming a three-dimensional network.

In the title tri-substituted thio­urea derivative, C13H18N2O3S, the thione-S and carbonyl-O atoms lie, to a first approximation, to the same side of the mol­ecule [the S—C—N—C torsion angle is −49.3 (2)°]. The CN2S plane is almost planar (r.m.s. deviation = 0.018 Å) with the hy­droxy­ethyl groups lying to either side of this plane. One hy­droxy­ethyl group is orientated towards the thio­amide functionality enabling the formation of an intra­molecular N—H⋯O hydrogen bond leading to an S(7) loop. The dihedral angle [72.12 (9)°] between the planes through the CN2S atoms and the 4-tolyl ring indicates the mol­ecule is twisted. The experimental mol­ecular structure is close to the gas-phase, geometry-optimized structure calculated by DFT methods. In the mol­ecular packing, hydroxyl-O—H⋯O(hydrox­yl) and hydroxyl-O—H⋯S(thione) hydrogen bonds lead to the formation of a supra­molecular layer in the ab plane; no directional inter­actions are found between layers. The influence of the specified supra­molecular inter­actions is apparent in the calculated Hirshfeld surfaces and these are shown to be attractive in non-covalent inter­action plots; the inter­action energies point to the important stabilization provided by directional O—H⋯O hydrogen bonds.

The PtII atom in the title complex, [Pt(C15H18N4O4S)(C2H6OS)], exists within a square-planar NS2O donor set provided by the N, S, O atoms of the di-anionic tridentate thio­semicarbazo ligand and a dimethyl sulfoxide S atom. The two chelate rings are coplanar, subtending a dihedral angle of 1.51 (7)°. The maximum deviation from an ideal square-planar geometry is seen in the five-membered chelate ring with an S—Pt—S bite angle of 96.45 (2)°. In the crystal, mol­ecules are linked via N—H⋯O, C—H⋯O, C—H⋯N and C—H⋯π inter­actions into two-dimensional networks lying parallel to the ab plane. The conformations of related cyclo­hexyl­hydrazine-1-carbo­thio­amide ligands are compared to that of the title compound.

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.