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The complete molecule of the title compound, C16H12Cl4N2O4, is generated by a crystallographic centre of symmetry. In the crystal, N—H...O hydrogen bonds link the molecules into [010] chains featuring R22(10) loops. The chains are cross-linked by short Cl...N contacts [3.224 (2) Å].

The title compound, C24H20N2O4·H2O, crystallizes with half a molecule of 2-(naphthalen-2-yloxy)-N′-[2-(naphthalen-2-yloxy)acetyl]acetohydrazide and half a water molecule in the asymmetric unit. In the crystal, molecules form planes parallel to (011). Two molecules are connected by water molecules via O—H...O and N—H...O hydrogen bonds.

The molecule of the title compound, C25H18ClF2N5S, comprises almost co-planar fluorophenyl, methylthiazolyl, pyrazolyl and chlorophenyl rings with the second fluorophenyl ring almost perpendicular to this plane. One fluorophenyl group is disordered over two components of occupancy ratio 0.767 (10):0.233 (10) related by a 24.2 (8)° twist. In the crystal, two molecules related by inversion symmetry are linked by a pair of C—H...F contacts in an R(8)22 geometry.

The molecule of the title compound, C26H17ClFN3OS, comprises benzofuranyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) ring systems. Rings A–D are almost coplanar, as indicated by the twist angles between the ring pairs A/B, B/C and C/D of 7.6 (1), 4.7 (1) and 6.9 (2)°, respectively. Ring E is twisted by 73.2 (1)° from the plane through ring C. In the crystal, pairwise C—H...F interactions link the molecules into inversion dimers. Aromatic π–π interactions are also observed between rings A and E and between rings B and C for neighbouring pairs of molecules related by inversion symmetry. Taken together, the weak interactions generate [010] chains.

The asymmetric unit of the title compound, C20H17N5O, consists of two independent molecules. The molecules comprise tolyl (A), triazolyl (B), pyrazolecarbaldehydyl (C) and phenyl (D) groups. The angles between the planes through neighouring rings A/B, B/C and C/D are 39.1 (1), 6.0 (1) and 12.6 (1)°, respectively, for the first molecule and 46.0 (1), 4.6 (1) and 8.5 (2)°, respectively, for the second. In the crystal, the two independent molecules form dimers linked by four C—H...O hydrogen bonds with each O atom accepting two such links.

The main molecule of the title dimethylformamide monosolvate, C28H20BrN7O2S·C3H7NO, comprises bromophenyl (A), thiadiazolyl (B), pyrazolyl (C), phenyl (D) and indolyl (E) ring systems with twist angles between the planes through neigbouring rings A/B, B/C, C/D and C/E of 33.7 (1), 14.8 (1), 60.7 (2) and 20.9 (1)°, respectively. In the crystal, the molecules are related by c-glide symmetry to form columns parallel to [001] which are linked by intermolecular N—H...O, C—H...O and C—H...Br contacts.

The title molecule, C22H21FN8O, comprises fluorophenyl (A), methyltriazolyl (B), methyltriazolyl (C) and tolyl (D) rings. The twist angles between the planes through neighbouring ring pairs A/B, B/C and C/D are 45.0 (1), 9.4 (1) and 43.2 (1)°, respectively. Intermolecular π–π interactions between rings A and C and between B and D propagate the structure in the [010] direction and weak C—H...O interactions also occur.

The title compound, C23H17ClFN5OS, comprises fluorophenyl (A), furanyl (B), pyrazolyl (C), methylthiazoyl (D) and chlorophenyl (E) rings. The B–C–D–E linked ring system is close to planar with the dihedral angles B/C, C/D and D/E being 7.6 (1), 3.4 (1) and 8.4 (1)°, respectively. The fluorophenyl group is almost perpendicular to the pyrazoyl ring, as indicated by an A/C twist angle of 79.4 (1)°. In the crystal, inversion dimers linked by pairs of C—H...S contacts are observed.

The title compound, C28H23FN6S, comprises phenyl (A), triazolyl (B), thiazolyl (C), pyrazoyl (D), tolyl (E) and fluorophenyl (F) rings, with twist angles between neighbouring rings pairs A/B, B/C, C/D, D/E and D/F of 64.6 (1), 11.7 (2), 23.5 (2), 8.2 (2) and 73.3 (1)°, respectively. A short intramolecular C—H...N contact and a weak intermolecular C—H...π interaction occur. The crystal chosen for data collection was found to be an inversion twin.

The title molecule, C25H17ClFN3S, contains indenothiazolyl (A), pyrazolyl (B), fluorophenyl (C) and chlorophenyl (D) groups. The dihedral angles between the ring planes A/B, B/C and B/D are 14.2 (1), 83.0 (1) and 6.5 (2)°, respectively. In the crystal, pairs of molecules related by inversion symmetry are linked by pairwise weak C—H...N interactions, forming dimers. These dimers interact through π–π contacts between the thiazolyl units [centroid-to-centroid distance = 3.826 (1) Å], forming chains along [010].

In the title solvate, C28H20ClN7O2S·C3H7NO, the main molecule consists of chlorophenyl (A), thiadiazolyl (B), pyrazolyl (C), phenyl (D) and indolyl (E) rings, with twist angles between neighbouring rings A/B, B/C, C/D and D/E of 32.6 (1), 14.8 (1), 60.8 (1) and 20.1 (1)°, respectively. The dimethylformamide solvent molecule accepts an N—H...O hydrogen bond from the indole group. In the extended structure, molecules related by 21 screw axes are stacked in the [001] direction to form columns linked by weak C—H...O interactions.

The title compound, C17H11ClN4O2, consists of chlorophenyl (A), isoxazolyl (B), oxadiazolyl (C) and phenyl (D) rings with twist angles between the planes through neighbouring rings A/B, B/C and C/D of 14.9 (1), 1.8 (1) and 8.9 (1)° respectively. In the crystal, adjacent molecules related by inversion symmetry form columns parallel to the [010] direction through π–π stacking [shortest centroid–centroid separation = 3.6203 (10) Å]; these are cross-linked by N—H...N interactions in the [001] direction.

N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide (3) was synthesized in a yield of 88% from an acid-catalyzed reaction of 5-methyl-1-phenyl-1H-1,2,3- triazole-4-carbohydrazide and 4-methoxybenzaldehyde in ethanol under reflux for 2.5 h. The structure of 3 was confirmed by the data obtained from infrared, nuclear magnetic resonance, mass spectroscopy, single crystal X-ray diffraction, and microanalysis.

The asymmetric unit of the title compound, 2C20H17BrN6S·C3H7NO, comprises two molecules of the thiazole derivative and one molecule of dimethylformamide (DMF) solvent. The twist angles between the planes through the bromophenyl, methylthiazolyl and indolyl groups are 10.1 (1) and 44.2 (1)°, respectively, for one molecule and 11.3 (1) and 1.6 (1)° for the other. In the crystal, N—H...N hydrogen bonds link four of the main molecules into tetramers. N—H...O bonds involving the DMF solvent molecule also occur.

The asymmetric unit comprises a single molecule of C17H17N5OS with twist angles between the planes through the thiophenyl, methyltriazolyl and tolyl groups of 12.3 (1) and 44.9 (1)°, respectively. A possible weak intramolecular hydrogen bond forms between the methyl substituent on the triazole ring and the adjacent carbonyl O atom. In the crystal structure, π–π interactions occur between phenyl rings of pairs of molecules related by inversion symmetry with a centroid–centroid separation of 3.7647 (18) Å. The shortest intermolecular hydrogen bonding contact is a C—H...O interaction that generates inversion dimers.

The conformation of the title compound, C25H24N4O3S, is influenced by an intramolecular N—H...O hydrogen bond, which generates an S(6) ring. The twist angles between the planes through the toluyl, methyltriazole, thiophene and phenyl rings are 60.1 (1), 33.5 (1) and 39.9 (1)°, respectively. In the crystal, molecules are stacked along the a-axis direction with weak aromatic π–π stacking interactions occurring between the thiophene rings [centroid-to-centroid distance = 3.7285 (15) Å].

In the title molecular salt, Na+·C10H7ClN3O2−, the dihedral angles between the planes of adjacent chlorophenyl, methyltriazole and carboxylate groups of the anion are 50.2 (1) and 9.0 (3)°, respectively. The shortest distance between sodium cations is 4.0595 (9) Å. The sodium cation is coordinated by two N atoms and three O atoms, generating layers of ions lying parallel to the bc plane.

In the title hydrate, C17H18N6O·H2O, the twist angles between the least-squares planes of the pyrolyl/methyltriazolyl/tolyl groups are 11.4 (2) and 7.9 (1)°, respectively. In the crystal, centrosymmetric tetramers (two organic molecules and two water molecules) are linked by N—H...O and O—H...O hydrogen bonds. Weak aromatic π–π stacking interactions between the triazolyl rings [centroid–centroid separation = 3.6422 (10) Å] link the tetramers.

The asymmetric unit of the title compound, C17H13N5O, comprises four independent molecules (A–D). The respective interplanar angles between the phenyl/oxadiazole/methyltriazole/phenyl rings for the four independent molecules are A 8.8 (2), 13.0 (2), 22.5 (2)°; B 6.3 (2), 8.9 (2), 29.0 (1)°; C 4.0 (2), 10.0 (2), 24.5 (2)°; D 3.5 (2), 10.1 (2), 27.2 (2)°. In the crystal, molecules form two separate stacks parallel to the b-axis direction: one consists of A and D molecules, and the other of B and C molecules. Aromatic π–π stacking is observed within each stack, with the shortest centroid–centroid separation being 3.552 (2) Å.

The title compound, C19H16N4O3, crystallizes with two molecules (A and B) in the asymmetric unit. In molecule A, the dihedral angles between the triazole ring and the toluyl and nitrobenzene rings are 62.68 (16) and 10.77 (15)°, respectively. The corresponding data for molecule B are 68.61 (17) and 15.59 (15)°, respectively. In the crystal, the B molecules are linked by C—H...N hydrogen bonds to generate [001] chains. Weak C—H...π(benzene) and N—O...π(triazole) contacts are also present.

In the title compound, C24H22N4O2S, the dihedral angle between the triazole and thiophene rings is 4.83 (14)°. The dihedral angles between the triazole and tolyl rings and between the thiophene and phenyl rings are 48.42 (16) and 9.23 (13)°, respectively. An intramolecular N—H...O hydrogen bond closes an S(6) loop. In the crystal, molecules are stacked parallel to the a-axis direction with weak π–π interactions between adjacent thiophenyl and triazolyl groups within the stack [centroid–centroid separation = 3.9811 (16) Å].

The asymmetric unit of the title compound, C37H28BrClN8S, comprises one molecule. The molecule consists of two ring systems joined by a C—C bond between the dihydropyrazolyl and pyrazolyl rings of the two extended ring systems. The angles between adjacent ring planes of the tolyl–triazolyl–pyrazolyl–phenyl ring system are 48.2 (1), 12.3 (2) and 22.2 (2)°, respectively, with angles of 19.7 (1), 5.6 (2) and 0.9 (2)° between the rings of the chlorophenyl–thiazolyl–dihydropyrazolyl–bromophenyl set. The pyrazolyl and dihydropyrazolyl rings are inclined at 68.3 (1)° to one another. In the crystal, C—H...Cl interactions form chains of molecules parallel to the b-axis direction.

In the title compound, C37H28Br2N8S, the dihedral angles between the planes of tolyl–triazolyl–pyrazolyl–phenyl rings are 47.5 (1), 11.4 (2) and 22.4 (2)°, respectively, and the angles between the bromophenyl–thiazolyl–dihydropyrazolyl–bromophenyl rings are 16.0 (2), 5.1 (2) and 0.8 (2)°, respectively. The dihedral angle between the planes of the pyrazolyl and dihydropyrazolyl rings is 67.7 (1)°. In the crystal, weak C—H...Br interactions form chains of molecules propagating in the [010] direction.

The asymmetric unit of the title compound, C20H18N8O2, comprises one complete molecule and a half molecule completed by crystallographic twofold symmetry leading to Z = 12. The dihedral angles between the planes of the linked phenyl and methyltriazolyl groups are 69.48 (5) and 44.85 (9)° for the first molecule and 42.88 (9)° for the second. The conformations of the diformyl hydrazyl groups of the molecules are similar as indicated by C—N—N—C torsion angles of −83.4 (2) and −86.4 (3)°. In the crystal, neighbouring molecules are linked by pairs of N—H...O hydrogen bonds to form independent columns propagating parallel to the c-axis direction.

The bromomethylphenyl and dimethylthiourea groups of the molecule of the title compound, C10H13BrN2S, are inclined to one another at an interplanar angle of 55.13 (6)°. In the crystal, molecules are stacked along the b axis and intermolecular N—H...S contacts form chains of molecules along [010].

In the title compound, C19H27F3N2OS2, the dihedral angle between the benzene ring and dithiocarbamate group is 67.00 (9)° and a weak intramolecular N—H...S interaction generates an S(7) ring. The tert-butyl group is disordered over two orientations in a 0.628 (14):0.372 (14) ratio. In the crystal, inversion dimers linked by pairs of weak C—H...O interactions generate R22(20) loops and the aromatic rings of neighbouring pairs of molecules are involved in very weak π–π stacking interactions [centroid–centroid separation = 4.0042 (13) Å].

The non-H atoms of the title molecule, C19H16N2O2, are almost coplanar (r.m.s. deviation = 0.019 Å), apart from the phenyl group, which is disordered with two components of almost equal occupancy: the dihedral angle between them is 78.9 (3)°. In the crystal, weak C—H...N hydrogen bonds link the molecules into [001] chains and aromatic π–π stacking interactions [shortest centroid–centroid separation = 3.747 (2) Å] form columns parallel to the c-axis direction.

In the title compound, C27H20BrN5O, the dihedral angle between the heterocyclic rings is 10.2 (2)°. The phenyl ring bound to the triazole ring is disordered over two orientations in a 0.808 (4):0.192 (4) ratio. In the crystal, C—H...O interactions form chains along [010]. π–π interactions are observed between the phenyl–pyrazolyl unit and the phenylene group of a neighbouring molecule.

The asymmetric unit of the title solvate, C17H16N8S2·0.25C3H7NO, consists of two C17H16N8S2 molecules and a dimethylformamide molecule disordered about a crystallographic inversion centre. Both triazole molecules feature an intramolecular C—H...N interaction, which generates an S(6) ring in each case. In the crystal, the components are linked by N—H...N and N—H...S hydrogen bonds to form [001] chains, which are cross-linked by weak C—H...O, C—H...N and C—H...S interactions.

In the title molecule, C8H7BrClNO2, the bromochlorophenyl ring is inclined to the methylcarbamate unit by 32.73 (7)°. In the crystal, N—H...O hydrogen bonds form chains of molecules parallel to [100].

The asymmetric unit of the title compound, C23H15N3OS, consists of two crystallographically independent molecules, which are related by a pseudo-inversion centre. In one molecule, the pyrazolyl ring makes dihedral angles of 35.7 (4), 19.1 (1) and 47.3 (1)°, respectively, with the thiophenyl ring, the attached phenyl ring and the phenyl ring of the benzoyl group. In the second molecule, the corresponding values are 37.4 (1), 16.1 (1) and 48.2 (1)°, respectively. In the crystal, the two independent molecules are linked to each other via a π–π interaction between the pyrazolyl rings [centroid–centroid distance = 3.578 (12) Å]. Weak intermolecular C—H...O interactions are also observed. The thiophenyl ring of one molecule is disordered over two orientations, with a refined occupancy ratio of 0.768 (3):0.232 (3).

The asymmetric unit of the title compound, C18H13F2N3O, comprises two molecules with similar conformations. In the crystal, weak C—H...F interactions form chains of molecules and the chains are stacked to form layers parallel to (101).

In the title compound, C37H28BrClN8O, the linked chlorophenyl, pyrazolyl and thiazolyl ringss are almost coplanar, with dihedral angles of 0.6 (3)° between the chlorophenyl and pyrazolyl rings and 5.4 (3)° between the pyrazolyl and thiazolyl rings. The dihedral angle between the thiazolyl and bromophenyl rings is 17.5 (2)°. The central pyrazolyl rings subtend a dihedral angle of 67.7 (1)°. In the crystal, π–π and C—H...Br interactions link the molecules to form columns parallel to [010]. The π–π interactions involve partially overlapping nonparallel bromophenyl and tolyl groups.

In the title compound, C10H11F3N2O, the dihedral angle between the dimethylurea and phenyl group planes is 37.49 (7)°. In the crystal, molecules are linked by N—H...O hydrogen bonds, generating chains propagating in the [010] direction. The trifluoromethyl group is disordered over two orientations in a 0.577 (12):0.423 (12) ratio.

In the title compound, C15H16N4O3S, the dihedral angle between the aromatic rings is 15.90 (19)°. The molecule features two intramolecular N—H...O hydrogen bonds, which both close S(6) rings. In the crystal, weak C—H...O interactions link the molecules into [010] chains.

In the title compound, C12H13N3O, the p-tolyl ring is twisted away from the mean plane (r.m.s. deviation = 0.044 Å) of the rest of the molecule by 50.84 (6)°. In the crystal, molecules are linked by C—H...π interactions, forming zigzag chains propagating in the b-axis direction.

The title compound, C13H9NO4, is almost planar (r.m.s. deviation = 0.071 Å). In the crystal, weak C—H...O and C—H...N interactions connect the molecules into ribbons propagating parallel to the a-axis direction.

Lithiation of N'-benzyl-N,N-dimethylurea and its substituted derivatives with t-BuLi (3.3 equiv) in anhydrous THF at 0 °C followed by reaction with various electrophiles afforded a range of 3-substituted isoindolin-1-ones in high yields.

The theoretical and experimental vibrational frequencies of 3-(diacetylamino)-2-ethyl-3H-quinazolin-4-one (2) were investigated. The experimental Laser-Raman spectrum (4000–100 cm−1) and FT-IR spectrum (4000–400 cm−1) of the newly synthesized compound were recorded in the solid phase. Both the theoretical vibrational frequencies and the optimized geometric parameters such as bond lengths and bond angles have for the first time been calculated using density functional theory (DFT/B3LYP and DFT/M06-2X) quantum chemical methods with the 6-311++G(d,p) basis set using Gaussian 03 software. The vibrational frequencies were assigned with the help of potential energy distribution (PED) analysis using VEDA 4 software. The calculated vibrational frequencies and the optimized geometric parameters were found to be in good agreement with the corresponding reported experimental data. Also, the energies of the lowest unoccupied molecular orbital (LUMO), highest occupied molecular orbital (HOMO), and other related molecular energies for 3-(diacetylamino)-2-ethyl-3H-quinazolin-4-one (2) have been investigated using the same computational methods.

In the title compound, C12H7N3O2S, the dihedral angle between the planes of the thiazolopyridine ring system (r.m.s. deviation = 0.005 Å) and the benzene ring is 3.94 (6)°. The nitro group is rotated by 7.6 (2)° from its attached ring. In the crystal, extensive aromatic π–π stacking [shortest centroid–centroid separation = 3.5295 (9) Å] links the molecules into (001) sheets.

In the title compound, C12H14N2S, the cyclohexane ring adopts a chair conformation with the exocyclic C—C bond in an equatorial orientation. The mean plane through the cyclohexane ring (all atoms) is twisted from the thiazolopyridine ring system (r.m.s. deviation = 0.013 Å) by 39.57 (6)°. In the crystal, molecules form (100) sheets, although there are no specific directional interactions between them. The crystal stucture was refined as a two-component perfect twin.

The molecule of the title compound, C10H11N3O, is planar, including the ethyl group, as indicated by the N—C—C—C torsion angle of 1.5 (2)°. In the crystal, inversion-related molecules are stacked along the a axis. Molecules are oriented head-to-tail and display π–π interactions with a centroid-to-centroid distance of 3.6664 (8) Å. N—H...O hydrogen bonds between molecules generate a `step' structure through formation of an R22(10) ring.

In the title molecule, C11H13N3O, the propyl group is almost perpendicular to the quinazolin-4(3H)-one mean plane, making a dihedral angle of 88.98 (9)°. In the crystal, molecules related by an inversion centre are paired via π–π overlap, indicated by the short distances of 3.616 (5) and 3.619 (5) Å between the centroids of the aromatic rings of neighbouring molecules. Intermolecular N—H...N and N—H...O hydrogen bonds form R66(30) rings and C(5) chains, respectively, generating a three-dimensional network. Weak C—H...O interactions are also observed.

In the title molecule, C13H10N2S, the dihedral angle between the planes through the non-H atoms of the methylbenzene and thiazolopyridine groups is 36.61 (5)°. In the crystal, the thiazolopyridine groups of inversion-related molecules overlap, with a minimum ring-centroid separation of 3.6721 (9) Å. Furthermore, the methylbenzene groups from neighbouring molecules interact edge-to-face at an angle of 71.66 (5)°. In addition, weak C—H... N hydrogen bonds form chains exending along [100].

There are two molecules in the asymmetric unit of the title compound, C11H16N2O. The pyridine rings and amide groups overlap almost perfectly (r.m.s. overlay fit = 0.053 Å), but the tertiary butyl groups have different orientations: in one molecule, one of the methyl C atoms is syn to the amide O atom [O—C—C—C = −0.8 (3)°] and in the other the equivalent torsion angle is 31.0 (2)°. In the crystal, the two independent molecules are linked by a pair of N—H...N hydrogen bonds in the form of an R22(8) loop to form a dimer. A C—H...O interaction connects the dimers into [100] chains.

In the title molecule, C9H10N2S, one of the methyl groups is almost co-planar with the thiazolopyridine rings with a deviation of 0.311 (3) Å from the least-squares plane of the thiazolopyridine group. In the crystal, weak C—H...N hydrogen-bonding interactions lead to the formation of chains along [011].

In the title compound, C10H14N2O, the pyridine ring is inclined to the mean plane of the amide moiety [N—C(=O)C] by 17.60 (8)°. There is an intramolecular C—H...O hydrogen bond present involving the carbonyl O atom. In the crystal, molecules are linked via N—H...N hydrogen bonds, forming chains propagating along [100]. The tert-butyl group is disordered over two sets of sites with a refined occupancy ratio of 0.758 (12):0.242 (12).

The title compound, C9H8N2O, is almost planar, with the C atom of the methoxy group deviating from the mean plane of the quinazoline ring system (r.m.s. deviation = 0.011 Å) by 0.068 (4) Å. In the crystal, molecules form π–π stacks parallel to the b-axis direction [centroid–centroid separation = 3.5140 (18) Å], leading to a herringbone packing arrangement.