Calibration of area detectors from powder diffraction standards is widely used at synchrotron beamlines. From a single diffraction image, it is not possible to determine both the sample-to-detector distance and the wavelength, but, with images taken from multiple positions along the beam direction and where the relative displacement is known, the sample-to-detector distance and wavelength can both be determined with good precision. An example calibration using the GSAS-II software package is presented.

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The transmembrane intracellular lectin ER–Golgi intermediate compartment protein 53 (ERGIC-53) and the soluble EF-hand multiple coagulation factor deficiency protein 2 (MCFD2) form a complex that functions as a cargo receptor, trafficking various glycoproteins between the endoplasmic reticulum (ER) and the Golgi apparatus. It has been demonstrated that the carbohydrate-recognition domain (CRD) of ERGIC-53 (ERGIC-53CRD) interacts with N-linked glycans on cargo glycoproteins, whereas MCFD2 recognizes polypeptide segments of cargo glycoproteins. Crystal structures of ERGIC-53CRD complexed with MCFD2 and mannosyl oligosaccharides have revealed protein–protein and protein–sugar binding modes. In contrast, the polypeptide-recognition mechanism of MCFD2 remains largely unknown. Here, a 1.60 Å resolution crystal structure of the ERGIC-53CRD–MCFD2 complex is reported, along with three other crystal forms. Comparison of these structures with those previously reported reveal that MCFD2, but not ERGIC-53–CRD, exhibits significant conformational plasticity that may be relevant to its accommodation of various polypeptide ligands.

Structures of the immunodominant protein P46 from M. hyopneumoniae has been determined by X-ray crystallography and it is shown that P46 can bind a diversity of oligosaccharides, particularly xylose, which exhibits a very high affinity for this protein. Structures of a monoclonal antibody, both alone and in complex with P46, that was raised against M. hyopnemoniae cells and specifically recognizes P46 are also reported.

While the crystal structure analysis of the title compound, C26H38O15, a synthetic derivative of sucrose, was originally reported 40 years ago [Drew et al. (1979). Carbohydr. Res. 71, 35–42], the present work has allowed for the determination of its absolute configuration through the application of resonant scattering techniques.

The title compound, [Ag2(C2H3O2)2(C19H20N2)2] (2), was readily synthesized by treatment of 3-benzyl-1-(2,4,6-tri­methyl­phen­yl)imidazolium chloride with silver acetate. The solution structure of the complex was analyzed by NMR spectroscopy, while the solid-state structure was confirmed by single-crystal X-ray diffraction studies. Compound 2 crystallizes in the triclinic space group Poverline{1}, with a silver-to-carbene bond length (Ag—CNHC) of 2.084 (3) Å. The mol­ecule resides on an inversion center, so that only half of the mol­ecule is crystallographically unique. The planes defined by the two imidazole rings are parallel to each other, but not coplanar [inter­planar distance is 0.662 (19) Å]. The dihedral angles between the imidazole ring and the benzyl and mesityl rings are 77.87 (12) and 72.86 (11)°, respectively. The crystal structure features π–π stacking inter­actions between the benzylic groups of inversion-related (−x + 1, −y + 1, −z + 1) mol­ecules and C—H⋯π inter­actions.

The synthesis and crystal structure of the title PtII complex, [Pt(C23H16N)Cl(CH3CN)], based on the C,N-chelating 2,4,6-tri­phenyl­pyridine as the primary ligand, is described. The central PtII atom is in a distorted square-planar coordination environment. In the crystal, mol­ecules are arranged via a metallophilic inter­action between platinum atoms with a Pt⋯Pt contact of 7.052 (2) Å. In addition, a π–π inter­action occurs.

The title hepta­nuclear alkoxido(oxido)vanadium(V) oxide cluster complex, [V7(C10H19O)O17(C18H24N2)3]·CH3CN, was obtained by the reaction of [V8O20(C18H24N2)4] with 4-tert-butyl­cyclo­hexa­nol (mixture of cis and trans) in a mixed CHCl3/CH3CN solvent. The complex has a V7O18N6 core with approximately Cs symmetry, which is composed of two VO4 tetra­hedra, two VO6 octa­hedra and three VO4N2 octa­hedra. In the crystal, these complexes are linked together by weak inter­molecular C—H⋯O hydrogen bonds between the 4,4'-di-tert-butyl-2,2'-bi­pyridine ligand and the V7O18N6 core, forming a one-dimensional network along the c-axis direction. Besides the complex, the asymmetric unit contains one CH3CN solvent mol­ecule. The contribution of other disordered solvent mol­ecules to the scattering was removed using the SQUEEZE option in PLATON [Spek (2015). Acta Cryst. C71, 9–18]. The unknown solvent mol­ecules are not considered in the chemical formula and other crystal data.

The crystal structure of pirfenidone, C12H11NO [alternative name: 5-methyl-1-phenyl­pyridin-2(1H)-one], an active pharmaceutical ingredient (API) approved in Europe and Japan for the treatment of Idiopathic pulmonary fibrosis (IPF), is reported here for the first time. It was crystallized from toluene by the temperature gradient technique, and crystallizes in the chiral monoclinic space group P21. The phenyl and pyridone rings are inclined to each other by 50.30 (11)°. In the crystal, mol­ecules are linked by C–H⋯O hydrogen bonds involving the same acceptor atom, forming undulating layers lying parallel to the ab plane.

The title Schiff base compound, C13H9ClN4O5·0.5CH3CN, crystallizes as an aceto­nitrile hemisolvate; the solvent mol­ecule being located on a twofold rotation axis. The mol­ecule is nearly planar, with a dihedral angle between the two benzene rings of 3.7 (2)°. The configuration about the C=N bond is E, and there is an intra­molecular N—H⋯Onitro hydrogen bond present forming an S(6) ring motif. In the crystal, mol­ecules are linked by O—H⋯O and N—H⋯O hydrogen bonds, forming layers lying parallel to (10overline{1}). The layers are linked by C—H⋯Cl hydrogen bonds, forming a supra­molecular framework. Within the framework there are offset π–π stacking inter­actions [inter­centroid distance = 3.833 (2) Å] present involving inversion-related mol­ecules. The DFT study shows that the HOMO and LUMO are localized in the plane extending from the phenol ring to the 2,4-di­nitro­benzene ring, and the HOMO–LUMO gap is found to be 0.13061 a.u.

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.

In the title bis­chalcone, C17H12Br2O, the olefinic double bonds are almost coplanar with their attached 4-bromo­phenyl rings [torsion angles = −10.2 (4) and −6.2 (4)°], while the carbonyl double bond is in an s-trans conformation with with respect to one of the C=C bonds and an s-cis conformation with respect to the other [C=C—C=O = 160.7 (3) and −15.2 (4)°, respectively]. The dihedral angle between the 4-bromo­phenyl rings is 51.56 (2)°. In the crystal, mol­ecules are linked into a zigzag chain propagating along [001] by weak C—H⋯π inter­actions. The conformations of related bis­chalcones are surveyed and a Hirshfeld surface analysis is used to investigate and qu­antify the inter­molecular contacts.

The title mol­ecule, C11H8F3NO3, adopts a cis configuration across the –C=C– double bond in the side chain and the dihedral angle between the phenyl ring and side chain is 47.35 (1)°. The –COOH group adopts a syn conformation (O=C—O—H = 0°), unlike the anti conformation observed in related maleamic acids. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds are connected via N—H⋯O hydrogen bonds and C—H⋯O inter­actions into (100) sheets, which are cross-linked by another C—H⋯O inter­action to result in a three-dimensional network. The Hirshfeld surface fingerprint plots show that the highest contribution to surface contacts arises from O⋯H/H⋯O contacts (26.5%) followed by H⋯F/F⋯H (23.4%) and H⋯H (17.3%).

The title compound, C15H15NO2, is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The mol­ecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intra­molecular N—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent mol­ecules into inversion dimers with an R22(18) ring motif. The dimers are linked by very weak π–π inter­actions, forming layers parallel to (overline{2}01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol­ecular electrostatic potential surfaces were used to analyse the inter­molecular inter­actions, indicating that the most important contributions for the crystal packing are from H⋯H (55.2%), C⋯H/H⋯C (22.3%) and O⋯H/H⋯O (13.6%) inter­actions.

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 compound, C14H12N2O4, is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The mol­ecule is almost planar, the rings making a dihedral angle of 4.99 (7)°. The mol­ecular structure is stabilized by an intra­molecular N—H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, inversion-related mol­ecules are linked by pairs of O—H⋯O hydrogen bonds, forming dimers with an R22(18) ring motif. The dimers are linked by pairs of C—H⋯O contacts with an R22(10) ring motif, forming ribbons extended along the [2overline{1}0] direction. Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol­ecular electrostatic potential surfaces were used to analyse the inter­molecular inter­actions present in the crystal, indicating that the most important contributions for the crystal packing are from H⋯H (33.9%), O⋯H/H⋯O (29.8%) and C⋯H/H⋯C (17.3%) inter­actions.

The title compound, C15H13BrO2S, comprises three different substituents bound to a central (and chiral) methine-C atom, i.e. (4-bromo­phen­yl)sulfanyl, benzaldehyde and meth­oxy residues: crystal symmetry generates a racemic mixture. A twist in the mol­ecule is evident about the methine-C—C(carbon­yl) bond as evidenced by the O—C—C—O torsion angle of −20.8 (7)°. The dihedral angle between the bromo­benzene and phenyl rings is 43.2 (2)°, with the former disposed to lie over the oxygen atoms. The most prominent feature of the packing is the formation of helical supra­molecular chains as a result of methyl- and methine-C—H⋯O(carbon­yl) inter­actions. The chains assemble into a three-dimensional architecture without directional inter­actions between them. The nature of the weak points of contacts has been probed by a combination of Hirshfeld surface analysis, non-covalent inter­action plots and inter­action energy calculations. These point to the importance of weaker H⋯H and C—H⋯C inter­actions in the consolidation of the structure.

A new polymorph of the title compound, C10H13NO, was obtained by recrystallization of the commercial product from a water/ethanol mixture (1:1 v/v). Crystals of the previously reported racemic and homochiral forms of 2-phenyl­butyramide were grown from water–aceto­nitrile solution in 1:1 volume ratio [Khrustalev et al. (2014). Cryst. Growth Des. 14, 3360–3369]. While the previously reported racemic and enanti­opure forms of the title compound adopt very similar supra­molecular structures (hydrogen-bonded ribbons), the new racemic polymorph is stabilized by a single N—H⋯O hydrogen bond that links mol­ecules into chains along the c-axis direction with an anti­parallel (centrosymmetric) packing in the crystal. Hirshfeld mol­ecular surface analysis was employed to compare the inter­molecular inter­actions in the polymorphs of the title compound.

The title compound, C9H11NO2, was obtained as unexpected product from the reaction of (4-{2-benz­yloxy-5-[(E)-(3-chloro-4-methyl­phen­yl)diazen­yl]benzyl­idene}-2-phenyl­oxazol-5(4H)-one) with 2-meth­oxy­aniline in the presence of acetic acid as solvent. The amide group is not coplanar with the benzene ring, as shown by the C—N—C—O and C—N—C—C torsion angles of −2.5 (3) and 176.54 (19)°, respectively. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (53.9%), C⋯H/H⋯C (21.4%), O⋯H/H⋯O (21.4%) and N⋯H/H⋯N (1.7%) inter­actions.

The title compound, [Ni(C10H8N2)3](C9H5N4O)2·2H2O, crystallizes as a racemic mixture in the monoclinic space group C2/c. In the crystal, the 1,1,3,3-tetracyano-2-ethoxypropenide anions and the water molecules are linked by O—H⋯N hydrogen bonds, forming chains running along the [010] direction. The bpy ligands of the cation are linked to the chain via C—H⋯π(cation) inter­actions involving the CH3 group. The inter­molecular inter­actions were investigated by Hirshfeld surface analysis and two-dimensional fingerprint plots.

The title compound (systematic name: bis­{2-[4-(acet­yloxy)-1H-indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C14H19N2O2+·C4H2O42−, has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N—H⋯O hydrogen bonds between the ammonium H atoms and the fumarate O atoms, as well as N—H⋯O hydrogen bonds between the indole H atoms and the fumarate O atoms. The hydrogen bonds hold the ions together in infinite one-dimensional chains along [111].

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.

In the title quinoline derivative, C14H14ClNO3, there is an intra­molecular C—H⋯O hydrogen bond forming an S(6) graph-set motif. The mol­ecule is essentially planar with the mean plane of the ethyl acetate group making a dihedral angle of 5.02 (3)° with the ethyl 6-chloro-2-eth­oxy­quinoline mean plane. In the crystal, offset π–π inter­actions with a centroid-to-centroid distance of 3.4731 (14) Å link inversion-related mol­ecules into columns along the c-axis direction. Hirshfeld surface analysis indicates that H⋯H contacts make the largest contribution (50.8%) to the Hirshfeld surface.

A new quinoline-based hydrazone, C16H12ClN3, was synthesized by a condensation reaction of 2-chloro-3-formyl­quinoline with phenyl­hydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The mol­ecule adopts an E configuration with respect to the central C=N bond. In the crystal, mol­ecules are linked by a C—H⋯π-phenyl inter­action, forming zigzag chains propagating along the [10overline{3}] direction. The N—H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent mol­ecule, so linking the chains via weak N—H⋯π inter­actions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (35.5%), C⋯H/H⋯C (33.7%), Cl⋯H/H⋯Cl (12.3%), N⋯H/H⋯N (9.5%) contacts.

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.

The mol­ecular structure of the title compound, C17H14ClFO3, consists of a 4-chloro-3-fluoro­phenyl ring and a 3,4-di­meth­oxy­phenyl ring linked via a prop-2-en-1-one spacer. The mol­ecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The F and H atoms at the meta positions of the 4-chloro-3-fluoro­phenyl ring are disordered over two orientations, with an occupancy ratio of 0.785 (3):0.215 (3). In the crystal, mol­ecules are linked via pairs of C—H⋯O inter­actions with an R22(14) ring motif, forming inversion dimers. The dimers are linked into a tape structure running along [10overline{1}] by a C—H⋯π inter­action. The inter­molecular contacts in the crystal were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are H⋯H (25.0%), followed by C⋯H/H⋯C (20.6%), O⋯H/H⋯O (15.6%), Cl⋯H/H⋯Cl (10.7%), F⋯H/H⋯F (10.4%), F⋯C/C⋯F (7.2%) and C⋯C (3.0%).

The title compound, C21H16N2O2, consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties. The imidazolidine ring is oriented at dihedral angles of 79.10 (5) and 82.61 (5)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06 (5)°. In the crystal, inter­molecular C—HProp⋯OImdzln (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds link the mol­ecules into infinite chains along the b-axis direction. Two weak C—HPhen⋯π inter­actions are also observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (43.3%), H⋯C/C⋯H (37.8%) and H⋯O/O⋯H (18.0%) inter­actions. Hydrogen bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Computational chemistry indicates that the C—HProp⋯OImdzln hydrogen-bond energy in the crystal is −40.7 kJ mol−1. 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 coordination of the ligands with respect to the central atom in the complex bromido­tricarbon­yl[diphen­yl(pyridin-2-yl)phosphane-κ2N,P]rhenium(I) chloro­form disolvate, [ReBr(C17H14NP)(CO)3]·2CHCl3 or [κ2-P,N-{(C6H5)2(C5H5N)P}Re(CO)3Br]·2CHCl3, (I·2CHCl3), is best described as a distorted octa­hedron with three carbonyls in a facial conformation, a bromide atom, and a biting P,N-di­phenyl­pyridyl­phosphine ligand. Hirshfeld surface analysis shows that C—Cl⋯H inter­actions contribute 26%, the distance of these inter­actions are between 2.895 and 3.213 Å. The reaction between I and piperidine (C5H11N) at 313 K in di­chloro­methane leads to the partial decoord­ination of the pyridyl­phosphine ligand, whose pyridyl group is replaced by a piperidine mol­ecule, and the complex bromido­tricarbon­yl[diphen­yl(pyridin-2-yl)phosphane-κP](piperidine-κN)rhenium(I), [ReBr(C5H11N)(C17H14NP)(CO)3] or [P-{(C6H5)2(C5H5N)P}(C5H11N)Re(CO)3Br] (II). The mol­ecule has an intra­molecular N—H⋯N hydrogen bond between the non-coordinated pyridyl nitro­gen atom and the amine hydrogen atom from piperidine with D⋯A = 2.992 (9) Å. Thermogravimetry shows that I·2CHCl3 losses 28% of its mass in a narrow range between 318 and 333 K, which is completely consistent with two solvating chloro­form mol­ecules very weakly bonded to I. The remaining I is stable at least to 573 K. In contrast, II seems to lose solvent and piperidine (12% of mass) between 427 and 463 K, while the additional 33% loss from this last temperature to 573 K corresponds to the release of 2-pyridyl­phosphine. The contribution to the scattering from highly disordered solvent mol­ecules in II was removed with the SQUEEZE routine [Spek (2015). Acta Cryst. C71, 9-18] in PLATON. The stated crystal data for Mr, μ etc. do not take this solvent into account.

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 reaction of 2,5-bis­(pyridin-4-yl)-1,3,4-oxa­diazole (4-pox) and thio­cyanate ions, used as co-ligand with nickel salt NiCl2·6H2O, produced the title complex, [Ni(NCS)2(C12H8N4O)2(H2O)2]. The NiII atom is located on an inversion centre and is octa­hedrally coordinated by four N atoms from two ligands and two pseudohalide ions, forming the equatorial plane. The axial positions are occupied by two O atoms of coordinated water mol­ecules. In the crystal, the mol­ecules are linked into a three-dimensional network through strong O—H⋯N hydrogen bonds. Hirshfeld surface analysis was used to investigate the inter­molecular inter­actions in the crystal packing.

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.

In each of the two independent mol­ecules in the asymmetric unit of the title compound, [CdI2(C18H14N4O)], the N,O,N'-tridentate N'-[(E)-(phen­yl)(pyridin-2-yl-κN)methyl­idene]pyridine-2-carbohydrazide ligand and two iodide anions form an I2N2O penta­coordination sphere, with a distorted square-pyramidal geometry, with an I atom in the apical position. Both mol­ecules feature an intra­molecular N—H⋯N hydrogen bond. In the crystal, weak aromatic π–π stacking inter­actions [centroid–centroid separation = 3.830 (2) Å] link the mol­ecules into dimers.

Five new crystal structures of perfluoro­pyridine substituted in the 4-position with phen­oxy, 4-bromo­phen­oxy, naphthalen-2-yl­oxy, 6-bromo­naphthalen-2-yl­oxy, and 4,4'-biphen­oxy are reported, viz. 2,3,5,6-tetra­fluoro-4-phen­oxy­pyridine, C11H5F4NO (I), 4-(4-bromo­phen­oxy)-2,3,5,6-tetra­fluoro­pyridine, C11H4BrF4NO (II), 2,3,5,6-tetra­fluoro-4-[(naphthalen-2-yl)­oxy]pyridine, C15H7F4NO (III), 4-[(6-bromo­naphthalen-2-yl)­oxy]-2,3,5,6-tetra­fluoropyridine, C15H6BrF4NO (IV), and 2,2'-bis­[(perfluoro­pyridin-4-yl)­oxy]-1,1'-biphenyl, C22H8F8N2O2 (V). The dihedral angles between the aromatic ring systems in I–IV are 78.74 (8), 56.35 (8), 74.30 (7), and 64.34 (19)°, respectively. The complete mol­ecule of V is generated by a crystallographic twofold axis: the dihedral angle between the pyridine ring and adjacent phenyl ring is 80.89 (5)° and the equivalent angle between the biphenyl rings is 27.30 (5)°. In each crystal, the packing is driven by C—H⋯F inter­actions, along with a variety of C—F⋯π, C—H⋯π, C—Br⋯N, C—H⋯N, and C—Br⋯π contacts. Hirshfeld surface analysis was conducted to aid in the visualization of these various influences on the packing.

The title compound, C11H8O5·(CH3)2SO, is a new coumarin derivative. The asymmetric unit contains two coumarin mol­ecules (A and B) and two di­methyl­sulfoxide solvent mol­ecules (A and B). The dihedral angle between the pyran and benzene rings in the chromene moiety is 3.56 (2)° for mol­ecule A and 1.83 (2)° for mol­ecule B. In mol­ecule A, the dimethyl sulfoxide sulfur atom is disordered over two positions with a refined occupancy ratio of 0.782 (5):0.218 (5). In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming chains running along the c-axis direction. The chains are linked by C—H⋯O hydrogen bonds, forming layers parallel to the ac plane. In addition, there are also C—H⋯π and π–π inter­actions present within the layers. The inter­molecular contacts in the crystal have been analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots, which indicate that the most important contributions to the packing are from H⋯H (33.9%) and O⋯H/H⋯O (41.2%) contacts.

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 asymmetric unit of the centrosymmetric title salt solvate, 2C17H17F6N2O+· C4H4O42−·CH3CH2OH, (systematic name: 2-{[2,8-bis­(tri­fluoro­meth­yl)quinolin-4-yl](hy­droxy)meth­yl}piperidin-1-ium butane­dioate ethanol monosolvate) comprises two independent cations, with almost superimposable conformations and each approximating the shape of the letter L, a butane­dioate dianion with an all-trans conformation and an ethanol solvent mol­ecule. In the crystal, supra­molecular chains along the a-axis direction are sustained by charge-assisted hy­droxy-O—H⋯O(carboxyl­ate) and ammonium-N—H⋯O(carboxyl­ate) hydrogen bonds. These are connected into a layer via C—F⋯π(pyrid­yl) contacts and π–π stacking inter­actions between quinolinyl-C6 and –NC5 rings of the independent cations of the asymmetric unit [inter-centroid separations = 3.6784 (17) and 3.6866 (17) Å]. Layers stack along the c-axis direction with no directional inter­actions between them. The analysis of the calculated Hirshfeld surface reveals the significance of the fluorine atoms in surface contacts. Thus, by far the greatest contribution to the surface contacts, i.e. 41.2%, are of the type F⋯H/H⋯F and many of these occur in the inter-layer region. However, these contacts occur at separations beyond the sum of the van der Waals radii for these atoms. It is noted that H⋯H contacts contribute 29.8% to the overall surface, with smaller contributions from O⋯H/H⋯O (14.0%) and F⋯F (5.7%) contacts.

In the title mol­ecule, C17H23NO2, the di­hydro­indole portion is planar (r.m.s. deviation = 0.0157 Å) and the nonyl substituent is in an `extended' conformation. In the crystal, the nonyl chains inter­calate and the di­hydro­indole­dione units are associated through C—H⋯O hydrogen bonds to form micellar blocks. Based on the Hirshfeld surface analysis, the most important inter­molecular inter­action is the H⋯H inter­action.

The syntheses and crystal structures of the title compounds, C14H8F4N2O2 and C14H8F4N2O3, are reported. In each crystal, the packing is driven by C—H⋯F inter­tactions, along with a variety of C—H⋯O, C—O⋯π, and C—F⋯π contacts. Hirshfeld surface analysis was conducted to aid in the visualization of these various influences on the packing: they showed that the largest contributions to the surface contacts arise from H⋯F/F⋯H inter­actions, followed by H⋯H and O⋯H/H⋯O.

The title coordination polymer, {[Cu3(C4H4N3O9)3(SeO4)(OH)]·2H2O}n or ([Cu3(μ3-OH)(trgly)3(SeO4)]·2H2O), crystallizes in the monoclinic space group P21/c. The three independent Cu2+ cations adopt distorted square-pyramidal geometries with {O2N2+O} polyhedra. The three copper centres are bridged by a μ3-OH anion, leading to a triangular [Cu3(μ3-OH)] core. 2-(1,2,4-Triazol-4-yl)acetic acid (trgly-H) acts in a deprotonated form as a μ3-κ3N1:N2:O ligand. The three triazolyl groups bridge three copper centres of the hydroxo-cluster in an N1:N2 mode, thus supporting the triangular geometry. The [Cu3(μ3-OH)(tr)3] clusters serve as secondary building units (SBUs). Each SBU can be regarded as a six-connected node, which is linked to six neighbouring triangles through carboxyl­ate groups, generating a two-dimensional uninodal (3,6) coordination network. The selenate anion is bound in a μ3-κ3O1:O2:O3 fashion to the trinuclear copper platform. The [Cu3(OH)(trgly)3(SeO4)] coordination layers and guest water mol­ecules are linked together by numerous O—H⋯O and C—H⋯O hydrogen bonds, leading to a three-dimensional structure.

In the title compound, C27H30N4O6·H2O, the two dioxolo rings are in envelope conformations, while the pyran ring is in a twisted-boat conformation. The pyradizine ring is oriented at dihedral angles of 9.23 (6) and 12.98 (9)° with respect to the pyridine rings, while the dihedral angle between the two pyridine rings is 13.45 (10)°. In the crystal, O—Hwater⋯Opyran, O—Hwater⋯Ometh­oxy­meth­yl and O—Hwater⋯Npyridazine hydrogen bonds link the mol­ecules into chains along [010]. In addition, weak C—Hdioxolo⋯Odioxolo hydrogen bonds and a weak C—Hmeth­oxy­meth­yl⋯π inter­action complete the three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (55.7%), H⋯C/C⋯H (14.6%), H⋯O/O⋯H (14.5%) and H⋯N/N⋯H (9.6%) inter­actions. Hydrogen-bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Electrochemical measurements are also reported.

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 two isotypic title compounds, C14H8BrCl2N3O2, (I), and C14H8Cl3N3O2, (II), the substitution of one of the phenyl rings is different [Br for (I) and Cl for (II)]. Aromatic rings form dihedral angles of 60.9 (2) and 64.1 (2)°, respectively. Mol­ecules are linked through weak X⋯Cl contacts [X = Br for (I) and Cl for (II)], C—H⋯Cl and C—Cl⋯π inter­actions into sheets parallel to the ab plane. Additional van der Waals inter­actions consolidate the three-dimensional packing. Hirshfeld surface analysis of the crystal structures indicates that the most important contributions for the crystal packing for (I) are from C⋯H/H⋯C (16.1%), O⋯H/H⋯O (13.1%), Cl⋯H/H⋯Cl (12.7%), H⋯H (11.4%), Br⋯H/H⋯Br (8.9%), N⋯H/H⋯N (6.9%) and Cl⋯C/C⋯Cl (6.6%) inter­actions, and for (II), from Cl⋯H / H⋯Cl (21.9%), C⋯H/H⋯C (15.3%), O⋯H/H⋯O (13.4%), H⋯H (11.5%), Cl⋯C/C⋯Cl (8.3%), N⋯H/H⋯N (7.0%) and Cl⋯Cl (5.9%) inter­actions. The crystal of (I) studied was refined as an inversion twin, the ratio of components being 0.9917 (12):0.0083 (12).

The title compound, C8H4Br2O4·C2H6O2, crystallizes with one-half of a 2,5-di­bromo­terephthalic acid (H2Br2tp) mol­ecule and one-half of an ethyl­ene glycol (EG) mol­ecule in the the asymmetric unit. The whole mol­ecules are generated by application of inversion symmetry. The H2Br2tp mol­ecule is not planar, with the di­bromo­benzene ring system inclined by a dihedral angle of 18.62 (3)° to the carb­oxy­lic group. In the crystal, the H2Br2tp and EG mol­ecules are linked into sheets propagating parallel to (overline{1}01) through O—H⋯O hydrogen bonds, thereby forming R44 (12) and R44 (28) graph-set motifs. Br⋯O and weak π–π stacking inter­actions are also observed. Hirshfeld surface analysis was used to confirm the existence of these inter­actions.

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.

The reaction of 2-methyl­thio-5-amino-1,3,4-thia­diazole (Me-SNTD; C3H5N3S2) with copper(II) acetate monohydrate [Cu(OAc)2·H2O; C4H8CuO5] resulted in the formation of the title binuclear compound, [Cu2(C2H3O2)4(C3H5N3S2)2] or [Cu2(OAc)4(Me-SNTD)2]. The structure has triclinic (P overline{1}) symmetry with a crystallographic inversion centre located at the midpoint of the line connecting the Cu atoms in the dimer. These two Cu atoms of the dimer [Cu⋯Cu = 2.6727 (6) Å] are held together by four carboxyl­ate groups. Each Cu atom is further coordinated to the N atom of an Me-SNTD mol­ecule and exhibits a Jahn–Teller-distorted octa­hedral geometry. The dimers are connected into infinite chains by hydrogen bonds between the NH (Me-SNTD) and the carboxyl­ate groups of neighbouring mol­ecules, generating an R22(12) ring motif. The mol­ecules are further linked by C—H⋯π inter­actions between the thia­diazole rings and the methyl groups of the acetate units.