The di-substituted acetyl­ene residue in the title compound, C11H11NO3, is capped at either end by di-methyl­hydroxy and 4-nitro­benzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral angle = 9.4 (3)°]. The most prominent feature of the mol­ecular packing is the formation, via hy­droxy-O—H⋯O(hy­droxy) hydrogen bonds, of hexa­meric clusters about a site of symmetry overline{3}. The aggregates are sustained by 12-membered {⋯OH}6 synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C—H⋯O(nitro) inter­actions, involving both nitro-O atoms. The aforementioned inter­actions are readily identified in the calculated Hirshfeld surface. Computational chemistry indicates there is a significant energy, primarily electrostatic in nature, associated with the hy­droxy-O—H⋯O(hy­droxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker inter­molecular contacts.

In the title di­thio­glycoluril derivative, C19H20N4O3S2, there is a difference in the torsion angles between the thio­imidazole moiety and the meth­oxy­phenyl groups on either side of the mol­ecule [C—N—Car—Car = 116.9 (2) and −86.1 (3)°, respectively]. The N—C—N bond angle on one side of the di­thio­glycoluril moiety is slightly smaller compared to that on the opposite side, [110.9 (2)° cf. 112.0 (2)°], probably as a result of the steric effect of the methyl group. In the crystal, N—H⋯S hydrogen bonds link adjacent mol­ecules to form chains propagating along the c-axis direction. The chains are linked by C—H⋯S hydrogen bonds, forming layers parallel to the bc plane. The layers are then linked by C—H⋯π inter­actions, leading to the formation of a three-dimensional supra­molecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the mol­ecular inter­actions in the crystal.

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 title compound, C18H16N4O, consists of a 3,6-bis­(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl­oxy)meth­yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C—HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C—HPrp­oxy⋯π (Prp­oxy = prop-2-en-1-yl­oxy) inter­actions link the mol­ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter­actions being the dominant inter­actions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

Lapachol acetate [systematic name: 3-(3-methyl­but-2-en­yl)-1,4-dioxonaph­thalen-2-yl acetate], C17H16O4, was prepared using a modified high-yield procedure and its crystal structure is reported for the first time 80 years after its first synthesis. The full spectroscopic characterization of the mol­ecule is reported. The mol­ecular conformation shows little difference with other lapachol derivatives and lapachol itself. The packing is directed by inter­molecular π–π and C—H⋯O inter­actions, as described by Hirshfeld surface analysis. The former inter­actions make the largest contributions to the total packing energy in a ratio of 2:1 with respect to the latter.

The title compound, C11H9F3N4S, was synthesized from 2-(tri­fluoro­meth­yl)aniline by a multi-step reaction. It crystallizes in the non-centrosymmetric space group Pna21, with one mol­ecule in the asymmetric unit, and is constructed from a pair of aromatic rings [2-(tri­fluoro­meth­yl)phenyl and tetra­zole], which are twisted by 76.8 (1)° relative to each other because of significant steric hindrance of the tri­fluoro­methyl group at the ortho position of the benzene ring. In the crystal, very weak C—H⋯N and C—H⋯F hydrogen bonds and aromatic π–π stacking inter­actions link the mol­ecules into a three-dimensional network. To further analyse the inter­molecular inter­actions, a Hirshfeld surface analysis, as well as inter­action energy calculations, were performed.

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 title compound, C14H15BrClNO4, consists of a 5-bromo­indoline-2,3-dione unit linked to a 1-{2-[2-(2-chloro­eth­oxy)eth­oxy]eth­yl} moiety. In the crystal, a series of C—H⋯O hydrogen bonds link the molecules to form a supramolecular three-dimensional structure, enclosing R22(8), R22(12), R22(18) and R22(22) ring motifs. π–π contacts between the five-membered dione rings may further stabilize the structure, with a centroid–centroid distance of 3.899 (2) Å. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (28.1%), H⋯O/O⋯H (23.5%), H⋯Br/Br⋯H (13.8%), H⋯Cl/Cl⋯H (13.0%) and H⋯C/C⋯H (10.2%) inter­actions. Hydrogen bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined mol­ecular structure in the solid state. The HOMO—LUMO behaviour was elucidated to determine the energy gap. The chloro­eth­oxy­ethoxyethyl side chain atoms are disordered over two sets of sites with an occupancy ratio of 0.665 (8):0.335 (6).

The title compounds, 4-(5-acetamido-3-acetyl-2-methyl-2,3-di­hydro-1,3,4-thia­diazol-2-yl)phenyl benzoate, C20H19N3O4S (I), 4-(5-acetamido-3-acetyl-2-methyl-2,3-di­hydro-1,3,4-thia­diazol-2-yl)phenyl isobutyrate 0.25-hydrate, C17H21N3O4S·0.25H2O (II), 4-(5-acetamido-3-acetyl-2-methyl-2,3-di­hydro-1,3,4-thia­diazol-2-yl)phenyl propionate, C16H19N3O4S (III) and 4-(5-acetamido-3-acetyl-2-methyl-2,3-di­hydro-1,3,4-thia­diazol-2-yl)phenyl cinnamate chloro­form hemisolvate, C22H21N3O4S·0.5CHCl3 (IV), all crystallize with two independent mol­ecules (A and B) in the asymmetric unit in the triclinic Poverline{1} space group. Compound II crystallizes as a quaterhydrate, while compound IV crystallizes as a chloro­form hemisolvate. In compounds I, II, III (mol­ecules A and B) and IV (mol­ecule A) the five-membered thia­diazole ring adopts an envelope conformation, with the tetra­substituted C atom as the flap. In mol­ecule B of IV this ring is flat (r.m.s. deviation 0.044 Å). The central benzene ring is in general almost normal to the mean plane of the thia­diazole ring in each mol­ecule, with dihedral angles ranging from 75.8 (1) to 85.5 (2)°. In the crystals of all four compounds, the A and B mol­ecules are linked via strong N—H⋯O hydrogen bonds and generate centrosymmetric four-membered R44(28) ring motifs. There are C—H⋯O hydrogen bonds present in the crystals of all four compounds, and in I and II there are also C—H⋯π inter­actions present. The inter­molecular contacts in the crystals of all four compounds were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

The title salt, C10H21N2O+·C7H12NO4S−, comprises a 3-methacryl­amido-N,N,N-tri­methyl­propan-1-aminium cation and a 2-acryl­amido-2-methyl­propane-1-sulfonate anion. The salt crystallizes with two unique cation–anion pairs in the asymmetric unit of the ortho­rhom­bic unit cell. The crystal studied was an inversion twin with a 0.52 (4):0.48 (4) domain ratio. In the crystal, the cations and anions stack along the b-axis direction and are linked by an extensive series of N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network. Hirshfeld surface analysis was carried out on both the asymmetric unit and the two individual salts. The contribution of inter­atomic contacts to the surfaces of the individual cations and anions are also compared.

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 compound, C15H12ClNO3, consists of a 1,2-di­hydro­quinoline-4-carb­oxyl­ate unit with 2-chloro­ethyl and propynyl substituents, where the quinoline moiety is almost planar and the propynyl substituent is nearly perpendicular to its mean plane. In the crystal, the mol­ecules form zigzag stacks along the a-axis direction through slightly offset π-stacking inter­actions between inversion-related quinoline moieties which are tied together by inter­molecular C—HPrpn­yl⋯OCarbx and C—HChlethy⋯OCarbx (Prpnyl = propynyl, Carbx = carboxyl­ate and Chlethy = chloro­eth­yl) hydrogen bonds. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (29.9%), H⋯O/O⋯H (21.4%), H⋯C/C⋯ H (19.4%), H⋯Cl/Cl⋯H (16.3%) and C⋯C (8.6%) inter­actions. Hydrogen bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HPrpn­yl⋯OCarbx and C—HChlethy⋯OCarbx hydrogen bond energies are 67.1 and 61.7 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

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.

Instances of crystal structures that remain isomorphous in spite of some minor changes in their respective mol­ecules, such as change in a substituent atom/group, can provide insights into the factors that govern crystal packing. In this context, an accurate description of the crystal structures of an isomorphous pair that differ from each other only by a chlorine–methyl substituent, viz. 5''-(2-chloro­benzyl­idene)-4'-(2-chloro­phen­yl)-1'-methyl­dispiro­[acenaphthene-1,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione, C34H28Cl2N2O2, (I), and its analogue 1'-methyl-5''-(2-methyl­benzyl­idene)-4'-(2-methyl­phen­yl)di­spiro­[acenaphthene-1,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione, C36H34N2O2, (II), is presented. While there are two C—H⋯O weak inter­molecular inter­actions present in both (I) and (II), the change of substituent from chlorine to methyl has given rise to an additional weak C—H⋯O inter­molecular inter­action that is relatively stronger than the other two. However, the presence of the stronger C—H⋯O inter­action in (II) has not disrupted the validity of the chloro-methyl exchange rule. Details of the crystal structures and Hirshfeld analyses of the two compounds are presented.

In the title compound, C24H31N3O2, the mean plane of the central pyrazole ring [r.m.s. deviation = 0.095 Å] makes dihedral angles of 11.93 (9) and 84.53 (8)°, respectively, with the phenyl and benzene rings. There is a short intra­molecular N—H⋯N contact, which generates an S(5) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds link inversion-related mol­ecules into dimers, generating an R22(8) ring motif. The Hirshfeld surface analysis indicates that the most significant contribution involves H⋯H contacts of 68.6%

The crystal and mol­ecular structures of the title triorganotin di­thio­carbamate, [Sn(C6H5)3(C7H14NS2)], are described. The mol­ecular geometry about the metal atom is highly distorted being based on a C3S tetra­hedron as the di­thio­carbamate ligand is asymmetrically chelating to the tin centre. The close approach of the second thione-S atom [Sn⋯S = 2.9264 (4) Å] is largely responsible for the distortion. The mol­ecular packing is almost devoid of directional inter­actions with only weak phenyl-C—H⋯C(phen­yl) inter­actions, leading to centrosymmetric dimeric aggregates, being noted. An analysis of the calculated Hirshfeld surface points to the significance of H⋯H contacts, which contribute 66.6% of all contacts to the surface, with C⋯H/H⋯C [26.8%] and S⋯H/H⋯H [6.6%] contacts making up the balance.

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.

In the title inorganic mol­ecular salt, (N2H5)2SiF6, the silicon atom at the centre of the slightly distorted SiF6 octa­hedron [range of Si—F distances = 1.6777 (4)–1.7101 (4) Å] lies on a crystallographic inversion centre. In the crystal, the ions are connected by N—H⋯N and N—H⋯F hydrogen bonds; the former link the cations into [010] chains and the latter (some of which are bifurcated or trifurcated) link the ions into a three-dimensional network. The two-dimensional fingerprint plots show that F⋯H/H⋯F inter­actions dominate the Hirshfeld surface (75.5%) followed by H⋯H (13.6%) and N⋯H/H⋯N (8.4%) whereas F⋯F (1.9%) and F⋯N/N⋯F (0.6%) have negligible percentages. The title compound is isostructural with its germanium-containing analogue.

In the title compound, C24H22N4O4, the four pyridine rings are tilted slightly with respect to each other. The dihedral angles between the inner and outer pyridine rings are 12.51 (8) and 9.67 (9)°, while that between inner pyridine rings is 20.10 (7)°. Within the mol­ecule, intra­molecular C—H⋯O and C—H⋯N contacts are observed. In the crystal, adjacent mol­ecules are linked by π–π stacking inter­actions between pyridine rings and weak C—H⋯π inter­actions between a methyl H atom and the centroid of a pyridine ring, forming a two-dimensional layer structure extending parallel to the ac plane. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (52.9%) and H⋯C/C⋯H (17.3%) contacts.

The bicyclic imidazo[1,2-a]pyridine core of the title compound, C19H19N3, is relatively planar with an r.m.s. deviation of 0.040 Å. The phenyl ring is inclined to the mean plane of the imidazo[1,2-a]pyridine unit by 18.2 (1)°. In the crystal, mol­ecules are linked by N—H⋯H hydrogen bonds, forming chains along the c-axis direction. The chains are linked by C—H⋯π inter­actions, forming slabs parallel to the ac plane. The Hirshfeld surface analysis and fingerprint plots reveal that the crystal structure is dominated by H⋯H (54%) and C⋯H/H⋯C (35.6%) contacts. The crystal studied was refined as an inversion twin

The title compound, C18H18F2N2O3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. They differ essentially in the orientation of the pyridine ring with respect to the benzene ring; these two rings are inclined to each other by 53.3 (2)° in mol­ecule A and by 72.9 (2)° in mol­ecule B. The 3-(cyclo­propyl­meth­oxy) side chain has an extended conformation in both mol­ecules. The two mol­ecules are linked by a pair of C—H⋯O hydrogen bonds and two C—H⋯π inter­actions, forming an A–B unit. In the crystal, this unit is linked by N—H⋯O hydrogen bonds, forming a zigzag –A–B–A–B– chain along [001]. The chains are linked by C—H⋯N and C—H⋯F hydrogen bonds to form layers parallel to the ac plane. Finally, the layers are linked by a third C—H⋯π inter­action, forming a three-dimensional structure. The major contributions to the Hirshfeld surface are those due to H⋯H contacts (39.7%), followed by F⋯H/H⋯F contacts (19.2%).

The title compounds, 6-(naphthalen-1-yl)-6a-nitro-6,6a,6 b,7,9,11a-hexa­hydro­spiro­[chromeno[3',4':3,4]pyrrolo­[1,2-c]thia­zole-11,11'-indeno­[1,2-b]quinoxaline], C37H26N4O3S, (I), and 6'-(naphthalen-1-yl)-6a'-nitro-6',6a',6b',7',8',9',10',12a'-octa­hydro-2H-spiro­[ace­naphthyl­ene-1,12'-chromeno[3,4-a]indolizin]-2-one, C36H28N2O4, (II), are new spiro derivatives, in which both the pyrrolidine rings adopt twisted conformations. In (I), the five-membered thia­zole ring adopts an envelope conformation, while the eight-membered pyrrolidine-thia­zole ring adopts a boat conformation. An intra­molecular C—H⋯N hydrogen bond occurs, involving a C atom of the pyran ring and an N atom of the pyrazine ring. In (II), the six-membered piperidine ring adopts a chair conformation. An intra­molecular C—H⋯O hydrogen bond occurs, involving a C atom of the pyrrolidine ring and the keto O atom. For both compounds, the crystal structure is stabilized by inter­molecular C—H⋯O hydrogen bonds. In (I), the C—H⋯O hydrogen bonds link adjacent mol­ecules, forming R22(16) loops propagating along the b-axis direction, while in (II) they form zigzag chains along the b-axis direction. In both compounds, C—H⋯π inter­actions help to consolidate the structure, but no significant π–π inter­actions with centroid–centroid distances of less than 4 Å are observed.

In the title compound, C16H14N2O3S, the 1,3-benzoxazole ring system is essentially planar (r.m.s deviation = 0.004 Å) and makes a dihedral angle of 66.16 (17)° with the benzene ring of the meth­oxy­phenyl group. Two intra­molecular N—H⋯O and N—H⋯N hydrogen bonds occur, forming S(5) and S(7) ring motifs, respectively. In the crystal, pairs of C—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with R22(14) ring motifs, stacked along the b-axis direction. The inversion dimers are linked by C—H⋯π and π–π-stacking inter­actions [centroid-to-centroid distances = 3.631 (2) and 3.631 (2) Å], forming a three-dimensional network. Two-dimensional fingerprint plots associated with the Hirshfeld surface show that the largest contributions to the crystal packing come from H⋯H (39.3%), C⋯H/H⋯C (18.0%), O⋯H/H⋯O (15.6) and S⋯H/H⋯S (10.2%) inter­actions.

Amino­pyridine and phthalic acid are well known synthons for supra­molecular architectures for the synthesis of new materials for optical applications. The 2-amino­pyridinium hydrogen phthalate title salt, C5H7N2+·C8H5O4−, crystallizes in the non-centrosymmetric space group P21. The nitro­gen atom of the –NH2 group in the cation deviates from the fitted pyridine plane by 0.035 (7) Å. The plane of the pyridinium ring and phenyl ring of the anion are oriented at an angle of 80.5 (3)° to each other in the asymmetric unit. The anion features a strong intra­molecular O—H⋯O hydrogen bond, forming a self-associated S(7) ring motif. The crystal packing is dominated by inter­molecular N—H⋯O hydrogen bonds leading to the formation of 21 helices, with a C(11) chain motif. They propagate along the b axis and enclose R22(8) ring motifs. The helices are linked by C—H⋯O hydrogen bonds, forming layers parallel to the ab plane. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate and qu­antify the inter­molecular inter­actions in the crystal.

In the cation of the title salt, C9H12N3S+·Br−, the thia­zolidine ring adopts an envelope conformation with the C atom adjacent to the phenyl ring as the flap. In the crystal, N—H⋯Br hydrogen bonds link the components into a three-dimensional network. Weak π–π stacking inter­actions between the phenyl rings of adjacent cations also contribute to the mol­ecular packing. A Hirshfeld surface analysis was conducted to qu­antify the contributions of the different inter­molecular inter­actions and contacts.

The title mol­ecular salt, (C7H11N2)2[Hg2Cl6], crystallizes with two 4-(di­methyl­amino)­pyridinium cations (A and B) and two half hexa­chlorido­dimercurate(II) anions in the asymmetric unit. The organic cations exhibit essentially the same features with an almost planar pyridyl ring (r.m.s. deviations of 0.0028 and 0.0109 Å), which forms an inclined dihedral angle with the dimethyamino group [3.06 (1) and 1.61 (1)°, respectively]. The di­methyl­amino groups in the two cations are planar, and the C—N bond lengths are shorter than that in 4-(di­methyl­amino)­pyridine. In the crystal, mixed cation–anion layers lying parallel to the (010) plane are formed through N—H⋯Cl hydrogen bonds and adjacent layers are linked by C—H⋯Cl hydrogen bonds, forming a three-dimensional network. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above inter­molecular inter­actions, but also serve to further differentiate the weaker inter­molecular inter­actions formed by the organic cations and inorganic anions, such as π–π and Cl⋯Cl inter­actions. The powder XRD data confirms the phase purity of the crystalline sample. Furthermore, the vibrational absorption bands were identified by IR spectroscopy and the optical properties were studied by using optical UV–visible absorption spectroscopy.

The title imidazo[1,2-a] pyridine derivative, C13H8Br2N2, was synthesized via a single-step reaction method. The title mol­ecule is planar, showing a dihedral angle of 0.62 (17)° between the phenyl and the imidazo[1,2-a] pyridine rings. An intra­molecular C—H⋯N hydrogen bond with an S(5) ring motif is present. In the crystal, a short H⋯H contact links adjacent mol­ecules into inversion-related dimers. The dimers are linked in turn by weak C—H⋯π and slipped π–π stacking inter­actions, forming layers parallel to (110). The layers are connected into a three-dimensional network by short Br⋯H contacts. Two-dimensional fingerprint plots and three-dimensional Hirshfeld surface analysis of the inter­molecular contacts reveal that the most important contributions for the crystal packing are from H⋯Br/Br⋯H (26.1%), H⋯H (21.7%), H⋯C/C⋯H (21.3%) and C⋯C (6.5%) inter­actions. Energy framework calculations suggest that the contacts formed between mol­ecules are largely dispersive in nature. Analysis of HOMO–LUMO energies from a DFT calculation reveals the pure π character of the aromatic rings with the highest electron density on the phenyl ring, and σ character of the electron density on the Br atoms. The HOMO–LUMO gap was found to be 4.343 eV.

In the title pyrazoline derivative, C16H16N2O3·H2O, the pyrazoline ring has an envelope conformation with the substituted sp2 C atom on the flap. The pyrazoline ring makes angles of 86.73 (12) and 13.44 (12)° with the tris­ubstituted and disubstituted benzene rings, respectively. In the crystal structure, the mol­ecules are connected into chains running in the b-axis direction by O—H⋯N hydrogen bonding. Parallel chains inter­act through N—H⋯O hydrogen bonds and π–π stacking of the tris­ubstituted phenyl rings. The major contribution to the surface contacts are H⋯H contacts (44.3%) as concluded from a Hirshfeld surface analysis.

The benzo­pyran ring of the title com­pound, C16H11ClN2O2, is planar [maximum deviation = 0.079 (2) Å] and is almost perpendicular to the chloro­phenyl ring [dihedral angle = 86.85 (6)°]. In the crystal, N—H⋯O, O—H⋯N, C—H⋯O and C—H⋯Cl hydrogen bonds form inter- and intra­molecular inter­actions. The DFT/B3LYP/6-311G(d,p) method was used to determine the HOMO–LUMO energy levels. The mol­ecular electrostatic potential surfaces were investigated by Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyse the inter­molecular inter­actions in the mol­ecule.

The title compound, C22H15Cl2NOS, contains 1,4-benzo­thia­zine and 2,4-di­­chloro­benzyl­idene units, where the di­hydro­thia­zine ring adopts a screw-boat conformation. In the crystal, inter­molecular C—HBnz⋯OThz (Bnz = benzene and Thz = thia­zine) hydrogen bonds form corrugated chains extending along the b-axis direction which are connected into layers parallel to the bc plane by inter­molecular C—HMethy⋯SThz (Methy = methyl­ene) hydrogen bonds, en­closing R44(22) ring motifs. Offset π-stacking inter­actions between 2,4-di­­chloro­phenyl rings [centroid–centroid = 3.7701 (8) Å] and π-inter­actions which are associated by C—HBnz⋯π(ring) and C—HDchlphy⋯π(ring) (Dchlphy = 2,4-di­chloro­phen­yl) inter­actions may be effective in the stabilization of the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (29.1%), H⋯C/C⋯H (27.5%), H⋯Cl/Cl⋯H (20.6%) and O⋯H/H⋯O (7.0%) inter­actions. Hydrogen-bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HBnz⋯OThz and C—HMethy⋯SThz hydrogen-bond energies are 55.0 and 27.1 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

The asymmetric units of the title compounds both contain one nonplanar mol­ecule. In 4-benzyl-6-phenyl-4,5-di­hydro­pyridazin-3(2H)-one, C17H14N2O, (I), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 46.69 (9)°; the phenyl ring of the benzyl group is nearly perpendicular to the plane of the pyridazine ring, the dihedral angle being 78.31 (10)°. In methyl 2-[5-(2,6-di­chloro­benz­yl)-6-oxo-3-phenyl-1,4,5,6-tetra­hydropyridazin-1-yl]acetate, C20H16Cl2N2O3, (II), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 21.76 (18)°, whereas the phenyl ring of the di­chloro­benzyl group is inclined to the pyridazine ring by 79.61 (19)°. In the crystal structure of (I), pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with an R22(8) ring motif. In the crystal structure of (II), C—H⋯O hydrogen bonds generate dimers with R12(7), R22(16) and R22(18) ring motifs. The Hirshfeld surface analyses of compound (I) suggests that the most significant contributions to the crystal packing are by H⋯H (48.2%), C⋯H/H⋯C (29.9%) and O⋯H/H⋯O (8.9%) contacts. For compound (II), H⋯H (34.4%), C⋯H/H⋯C (21.3%) and O⋯H/H⋯O (16.5%) inter­actions are the most important contributions.

The title com­pound, C22H16N4O2, contains two pyridine rings and one meth­oxy­carbonyl­phenyl group attached to a pyridazine ring which deviates very slightly from planarity. In the crystal, ribbons consisting of inversion-related chains of mol­ecules extending along the a-axis direction are formed by C—HMthy⋯OCarbx (Mthy = methyl and Carbx = carboxyl­ate) hydrogen bonds. The ribbons are connected into layers parallel to the bc plane by C—HBnz⋯π(ring) (Bnz = benzene) inter­actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (39.7%), H⋯C/C⋯H (27.5%), H⋯N/N⋯H (15.5%) and O⋯H/H⋯O (11.1%) inter­actions. Hydrogen-bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Computational chemistry indicates that in the crystal, C—HMthy⋯OCarbx hydrogen-bond energies are 62.0 and 34.3 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are com­pared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

The crystal and mol­ecular structures of the title CuII complex, isolated as a dihydrate, [Cu(C21H14N3O3)2]·2H2O, reveals a highly distorted coordination geometry inter­mediate between square-planar and tetra­hedral defined by an N2O2 donor set derived from two mono-anionic bidentate ligands. Furthermore, each six-membered chelate ring adopts an envelope conformation with the Cu atom being the flap. In the crystal, imidazolyl-amine-N—H⋯O(water), water-O—H⋯O(coordinated, nitro and water), phenyl-C—H⋯O(nitro) and π(imidazol­yl)–π(nitro­benzene) [inter-centroid distances = 3.7452 (14) and 3.6647 (13) Å] contacts link the components into a supra­molecular layer lying parallel to (101). The connections between layers forming a three-dimensional architecture are of the types nitro­benzene-C—H⋯O(nitro) and phenyl-C—H⋯π(phen­yl). The distorted coordination geometry for the CuII atom is highlighted in an analysis of the Hirshfeld surface calculated for the metal centre alone. The significance of the inter­molecular contacts is also revealed in a study of the calculated Hirshfeld surfaces; the dominant contacts in the crystal are H⋯H (41.0%), O⋯H/H⋯O (27.1%) and C⋯H/H⋯C (19.6%).

A 1:1 epimeric mixture of 3-[(4-nitro­benzyl­idene)amino]-2(R,S)-(4-nitro­phen­yl)-5(S)-(propan-2-yl)imidazolidin-4-one, C19H19N5O5, was isolated from a reaction mixture of 2(S)-amino-3-methyl-1-oxo­butane­hydrazine and 4-nitro­benz­alde­hyde in ethanol. The product was derived from an initial reaction of 2(S)-amino-3-methyl-1-oxo­butane­hydrazine at its hydrazine group to provide a 4-nitro­benzyl­idene derivative, followed by a cyclization reaction with another mol­ecule of 4-nitro­benzaldehyde to form the chiral five-membered imidazolidin-4-one ring. The formation of the five-membered imidazolidin-4-one ring occurred with retention of the configuration at the 5-position, but with racemization at the 2-position. In the crystal, N—H⋯O(nitro) hydrogen bonds, weak C—H⋯O(carbon­yl) and C—H⋯O(nitro) hydrogen bonds, as well as C—H⋯π, N—H⋯π and π–π inter­actions, are present. These combine to generate a three-dimensional array. Hirshfeld surface analysis and PIXEL calculations are also reported.

The title com­pound, C15H11NO5, is relatively planar, with the planes of the two aromatic rings being inclined to each other by 3.09 (5)°. In the crystal, mol­ecules are linked by a pair of C—H⋯O hydrogen bonds, forming inversion dimers, which enclose an R22(16) ring motif. The dimers are linked by a further pair of C—H⋯O hydrogen-bonds forming ribbons enclosing R44(26) ring motifs. The ribbons are linked by offset π–π inter­actions [centroid–centroid distances = 3.6754 (6)–3.7519 (6) Å] to form layers parallel to the ac plane. Through Hirshfeld surface analyses, the dnorm surfaces, electrostatic potential and two-dimensional fingerprint (FP) plots were examined to verify the contributions of the different inter­molecular contacts within the supra­molecular structure. The shape-index surface shows that two sides of the mol­ecule are involved with the same contacts in neighbouring mol­ecules, and the curvedness plot shows flat surface patches that are characteristic of planar stacking.

In the title com­pound, C30H20Cl2O2Se, the C—Se—C angle is 99.0 (2)°, with the dihedral angle between the planes of the attached benzene rings being 79.1 (3)°. The average endocyclic angles (Se—C—C) facing the Se atom are 122.1 (5) and 122.2 (5)°. The Se atom is essentially coplanar with the attached benzene rings, deviating by 0.075 (1) and 0.091 (1) Å. In the two phenyl­ene(4-chloro­phen­yl)prop-2-en-1-one units, the benzene rings are inclined to each other by 44.6 (3) and 7.8 (3)°. In the crystal, the mol­ecules stack up the a axis, forming layers parallel to the ac plane. There are no significant classical inter­molecular inter­actions present. Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol­ecular electrostatic potential surface were used to analyse the crystal packing. The Hirshfeld surface analysis suggests that the most significant contributions to the crystal packing are by C⋯H/H⋯C contacts (17.7%).

In the title com­pound, C13H14N2O3, the dihydropyridazine ring (r.m.s. deviation = 0.166 Å) has a screw-boat conformation. The dihedral angle between its mean plane and the benzene ring is 0.77 (12)°. In the crystal, inter­molecular O—H⋯O hydrogen bonds generate C(5) chains and N—H⋯O hydrogen bonds produce R22(8) motifs. These types of inter­actions lead to the formation of layers parallel to (12overline{1}). The three-dimensional network is achieved by C—H⋯O inter­actions, including R24(8) motifs. Inter­molecular inter­actions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are by H⋯H (43.3%), H⋯C/C⋯H (19.3%), H⋯O/H⋯O (22.6%), C⋯N/N⋯C (3.0%) and H⋯N/N⋯H (5.8%) contacts. C—H⋯π inter­actions and aromatic π–π stacking inter­actions are not observed.

The title com­pound, C24H24N2O6, consists of ethyl 2-(1,2,3,4-tetra­hydro-2-oxo­quinolin-1-yl)acetate and 4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbomoyl] units, where the oxo­quinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C—HOxqn⋯OEthx and C—HPh­yl⋯OCarbx (Oxqn = oxoquinolin, Ethx = eth­oxy, Phyl = phenyl and Carbx = carboxyl­ate) weak hydrogen bonds link the mol­ecules into a three-dimensional network sturucture. A π–π inter­action between the constituent rings of the oxo­quinoline unit, with a centroid–centroid distance of 3.675 (1) Å may further stabilize the structure. Both terminal ethyl groups are disordered over two sets of sites. The ratios of the refined occupanies are 0.821 (8):0.179 (8) and 0.651 (18):0.349 (18). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (53.9%), H⋯O/O⋯H (28.5%) and H⋯C/C⋯H (11.8%) inter­actions. Weak inter­molecular hydrogen-bond inter­actions and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are com­pared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO mol­ecular orbital behaviour was elucidated to determine the energy gap.

2-(4-Nitro­phen­yl)-2-oxoethyl picolinate, C14H10N2O5, was synthesized under mild conditions. The chemical and mol­ecular structures were confirmed by single-crystal X-ray diffraction analysis. The mol­ecules are linked by inversion into centrosymmetric dimers via weak inter­molecular C—H⋯O inter­actions, forming R22(10) ring motifs, and further strengthened by weak π–π inter­actions. Hirshfeld surface analyses, the dnorm surfaces, electrostatic potential and two-dimensional fingerprint (FP) plots were used to verify the contributions of the different inter­molecular inter­actions within the supra­molecular structure. The shape-index surface shows that two sides of the mol­ecules are involved with the same contacts in neighbouring mol­ecules and curvedness plots show flat surface patches that are characteristic of planar stacking.

In the title com­plex, [Cu(C18H12F6N2O4)]·0.5C6H6O2, the CuII ion has a square-planar coordination geometry, being ligated by two N and two O atoms of the tetra­dentate open-chain Schiff base ligand 6,6'-{(1E,1'E)-[ethane-1,2-diylbis(aza­nylyl­idene)]bis­(methanylyl­idene)}bis­[2-(tri­fluoro­meth­oxy)phenol]. The crystal packing is stabilized by intra­molecular O—H⋯O and inter­molecular C—H⋯F, C—H⋯O and C—H⋯π hydrogen bonds. In addition, weak π–π inter­actions form a three-dimensional structure. Hirshfeld surface analysis and two-dimensional fingerprint plots were performed and created to analyze the inter­molecular inter­actions present in the crystal, indicating that the most important contributions for the crystal packing are from F⋯H/H⋯F (25.7%), H⋯H (23.5%) and C⋯H/H⋯C (12.6%) inter­actions.

The title compound, C15H10ClNO5, is relatively planar with the two aromatic rings being inclined to each other by 3.56 (11)°. The central —C(=O)—C–O—C(=O)— bridge is slightly twisted, with a C—C—O—C torsion angle of 164.95 (16)°. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯Cl hydrogen bonds, forming layers parallel to the (101) plane. The layers are linked by a further C—H⋯O hydrogen bond, forming a three-dimensional supra­molecular structure. There are a number of offset π–π inter­actions present between the layers [inter­centroid distances vary from 3.8264 (15) to 3.9775 (14) Å]. Hirshfeld surface analyses, the dnorm surfaces, electrostatic potential and two-dimensional fingerprint plots were examined to verify the contributions of the different inter­molecular contacts within the supra­molecular structure. The shape-index surface shows that two sides of the mol­ecule are involved in the same contacts with neighbouring mol­ecules, and the curvedness plot shows flat surface patches that are characteristic of planar stacking.

The crystal structure of the title compound, [Ni3(C8H4O4)3(C3H7NO)4], is a two-dimensional coordination network formed by trinuclear linear Ni3(tp)3(DMF)4 units (tp = terephthalate = benzene-1,4-di­carboxyl­ate and DMF = di­methyl­formamide) displaying a characteristic coordination mode of acetate groups in polynuclear metal–organic compounds. Individual trinuclear units are connected through tp anions in a triangular network that forms layers. One of the DMF ligands points outwards and provides inter­actions with equivalent planes above and below, leaving the second ligand in a structural void much larger than the DMF mol­ecule, which shows positional disorder. Parallel planes are connected mainly through weak C—H⋯O, H⋯H and H⋯C inter­actions between DMF mol­ecules, as shown by Hirshfeld surface analysis.

In the paper by Gomes et al. [Acta Cryst. (2019), E75, 1403–1410], there was an error and omission in the author and affiliation list.

In the title compound, (2,2'-bi­pyridine-κ2N,N')bis­(2-meth­oxy­ethyl xanthato-κS)zinc(II), [Zn(C4H7O2S2)2(C10H8N2)], the ZnII ion is coordinated to two N atoms of the 2,2'-bi­pyridine ligand and two S atoms from two 2-meth­oxy­ethyl xanthate ligands. The ZnII ion lies on a crystallographic twofold rotation axis and has distorted tetra­hedral coordination geometry. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming supramolecular chains propagating along the a-axis direction. Weak intra­molecular C—H⋯S hydrogen bonds are also observed. The inter­molecular contacts in the crystal were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are H⋯H (36.3%), followed by S⋯H/H⋯S (24.7%), C⋯H/H⋯C (15.1%), O⋯H/H⋯O (14.4%), N⋯H/H⋯N (4.1%) and C⋯C (2.9%).

In the title compound, C17H21NO4S, the 1,4-di­hydro­pyridine ring has an envelope conformation with the Csp3 atom at the flap. The thio­phene ring is nearly perpendicular to the best plane through the 1,4-di­hydro­pyridine ring, the dihedral angle being 82.19 (13)°. In the crystal, chains running along the b-axis direction are formed through N—H⋯O inter­actions between the 1,4-di­hydro­pyridine N atom and one of the O atoms of the ester groups. Neighbouring chains are linked by C—H⋯O and C—H⋯π inter­actions. A Hirshfeld surface analysis shows that the most prominent contributuion to the surface contacts are H⋯H contacts (55.1%).

In the title compound, C10H10N2OS, the five atoms of the thio­phene ring are essentially coplanar (r.m.s. deviation = 0.0037 Å) and the pyridazine ring is non-planar. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into dimers with an R22(8) ring motif. The dimers are linked by C—H⋯O inter­actions, forming layers parallel to the bc plane. The theoretical geometric parameters are in good agreement with XRD results. The inter­molecular inter­actions were investigated using a Hirshfeld surface analysis and two-dimensional fingerprint plots. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H⋯H (39.7%), C⋯H/H⋯C (17.3%) and O⋯H/H⋯O (16.8%) contacts.

The title pyridazinone derivative, C20H18N2O3, is not planar. The phenyl ring and the pyridazine ring are inclined to each other by 10.55 (12)°, whereas the 4-methyl­benzyl ring is nearly orthogonal to the pyridazine ring, with a dihedral angle of 72.97 (10)°. In the crystal, mol­ecules are linked by pairs of O—H⋯O hydrogen bonds, forming inversion dimers with an R22(14) ring motif. The dimers are linked by C—H⋯O hydrogen bonds, generating ribbons propagating along the c-axis direction. The inter­molecular inter­actions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. They revealed that the most significant contributions to the crystal packing are from H⋯H (48.4%), H⋯O/O⋯H (21.8%) and H⋯C/C⋯H (20.4%) contacts. Mol­ecular orbital calculations providing electron-density plots of HOMO and LUMO mol­ecular orbitals and mol­ecular electrostatic potentials (MEP) were also computed, both with the DFT/B3LYP/6–311 G++(d,p) basis set.

The title compound, C14H12BrNO2, was synthesized by the condensation reaction of 2,3-di­hydroxy­benzaldehyde and 2-bromo-3-methyl­aniline. It crystallizes in the centrosymmetric triclinic space group Poverline{1}. The configuration about the C=N bond is E. The dihedral angle between the planes of the 5-(2-bromo-3-methyl­phenyl ring and the catechol ring is 2.80 (17)°. In the crystal, O—H⋯O hydrogen-bond inter­actions consolidate the crystal packing.

In the title hydrated hybrid compound C14H14N2OS2·H2O, the planar imidazo[1,2-a]pyridine ring system is linked to the 1,3-di­thiol­ane moiety by an enone bridge. The atoms of the C—C bond in the 1,3-di­thiol­ane ring are disordered over two positions with occupancies of 0.579 (14) and 0.421 (14) and both disordered rings adopt a half-chair conformation. The oxygen atom of the enone bridge is involved in a weak intra­molecular C—H⋯O hydrogen bond, which generates an S(6) graph-set motif. In the crystal, the hybrid mol­ecules are associated in R22(14) dimeric units by weak C—H⋯O inter­actions. O—H⋯O hydrogen bonds link the water mol­ecules, forming infinite self-assembled chains along the b-axis direction to which the dimers are connected via O—H⋯N hydrogen bonding. Analysis of inter­molecular contacts using Hirshfeld surface analysis and contact enrichment ratio descriptors indicate that hydrogen bonds induced by water mol­ecules are the main driving force in the crystal packing formation.