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In the title compound, C19H17NO5S, the cyclohexene ring adopts nearly an envelope conformation. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming a three-dimensional network. In addition, C—H...π interactions connect the molecules by forming layers parallel to the (010) plane. According to the Hirshfeld surface analysis, H...H (36.9%), O...H/H...O (31.0%), C...H/H...C (18.9%) and S...H/H...S (7.9%) interactions are the most significant contributors to the crystal packing.

In the title compound, C20H17BrO5S, molecules are connected by intermolecular C—H...S hydrogen bonds with R22(10) ring motifs, forming ribbons along the b-axis direction. C—H...π interactions consolidate the ribbon structure while van der Waals forces between the ribbons ensure the cohesion of the crystal structure. According to a Hirshfeld surface analysis, H...H (40.5%), O...H/H...O (27.0%), C...H/H...C (13.9%) and Br...H/H...Br (11.7%) interactions are the most significant contributors to the crystal packing. The thiophene ring and its adjacent dicarboxylate group and the three adjacent carbon atoms of the central hexene ring to which they are attached were refined as disordered over two sets of sites having occupancies of 0.8378 (15) and 0.1622 (15). The thiophene group is disordered by a rotation of 180° around one bond.

The asymmetric unit of the title compound, C25H18N6·H2O, comproses two molecules (I and II), together with a water molecule. The terminal phenyl groups attached to the methyl groups of the molecules I and II do not overlap completely, but are approximately perpendicular. In the crystal, the molecules are connected by N—H...N, C—H...N, O—H...N and N—H...O hydrogen bonds with each other directly and through water molecules, forming layers parallel to the (001) plane. C—H...π interactions between these layers ensure the cohesion of the crystal structure. A Hirshfeld surface analysis indicates that H...H (39.1% for molecule I; 40.0% for molecule II), C...H/H...C (26.6% for molecule I and 25.8% for molecule II) and N...H/H...N (24.3% for molecules I and II) interactions are the most important contributors to the crystal packing.

In the ten-membered 1,3,4,6-tetrahydro-2H-pyrido[1,2-a]pyrimidine ring system of the title compound, C17H15N5, the 1,2-dihydropyridine ring is essentially planar (r.m.s. deviation = 0.001 Å), while the 1,3-diazinane ring has a distorted twist-boat conformation. In the crystal, molecules are linked by N—H...N and C—H...N hydrogen bonds, forming a three-dimensional network. In addition, C—H...π interactions form layers parallel to the (100) plane. Thus, crystal-structure cohesion is ensured. According to a Hirshfeld surface study, H...H (40.4%), N...H/H...N (28.6%) and C...H/H...C (24.1%) interactions are the most important contributors to the crystal packing.

In the title compound, C21H15N5OS2, molecular pairs are linked by N—H...N hydrogen bonds along the c-axis direction and C—H...S and C—H...O hydrogen bonds along the b-axis direction, with R22(12) and R22(16) motifs, respectively, thus forming layers parallel to the (10\overline{4}) plane. In addition, C=S...π and C[triple-bond]N...π interactions between the layers ensure crystal cohesion. The Hirshfeld surface analysis indicates that the major contributions to the crystal packing are H...H (43.0%), C...H/H...C (16.9%), N...H/H...N (11.3%) and S...H/H...S (10.9%) interactions.

In the crystal of the title compound, C6H9ClN2O, molecular pairs form dimers with an R22(8) motif through N—H...O hydrogen bonds. These dimers are connect into ribbons parallel to the (100) plane with R44(10) motifs by N—H...O hydrogen bonds along the c-axis direction. In addition, π–π [centroid-to-centroid distance = 3.4635 (9) Å] and C—Cl...π interactions between the ribbons form layers parallel to the (100) plane. The three-dimensional consolidation of the crystal structure is also ensured by Cl...H and Cl...Cl interactions between these layers. According to a Hirshfeld surface study, H...H (43.3%), Cl...H/H...Cl (22.1%) and O...H/H...O (18.7%) interactions are the most significant contributors to the crystal packing.

The title compound, C13H11NO, adopts an E configuration about the C=C double bond. The pyrrole ring is inclined to the phenyl ring at an angle of 44.94 (8)°. In the crystal, molecules are linked by N—H...O hydrogen bonds, forming ribbons parallel to (020) in zigzag C(7) chains along the a axis. These ribbons are connected via C—H...π interactions, forming a three-dimensional network. No significant π–π interactions are observed.

In the title compound, C15H14N2O2·H2O, the 1H-pyrrole ring makes a dihedral angle of 59.95 (13)° with the phenyl ring. In the crystal, the molecules are connected by C—H...O hydrogen bonds into layers parallel to the (020) plane, while two molecules are connected to the water molecule by two N—H...O hydrogen bonds and one molecule by an O—H...O hydrogen bond. C—H...π and π–π interactions further link the molecules into chains extending in the [\overline{1}01] direction and stabilize the molecular packing. According to a Hirshfeld surface study, H...H (49.4%), C...H/H...C (23.2%) and O...H/H...O (20.0%) interactions are the most significant contributors to the crystal packing.

In the title compound, C16H13BrO, the planes of the aromatic rings are inclined at an angle of 23.49 (15)°, and the configuration about the C=C bond is E. In the crystal, the molecules are linked into chains by weak C—H...O interactions along the b axis. Successive chains form a zigzag structure along the c axis, and these chains are connected to each other by face-to-face π–π stacking interactions along the a axis. These layers, parallel to the (001) plane, are linked by van der Waals interactions, thus consolidating the crystal structure. Hirshfeld surface analysis showed that the most significant contacts in the structure are H...H (43.1%), C...H/H...C (17.4%), Br...H/H...Br (14.9%), C...C (11.9%) and O...H/H...O (9.8%).

In the hydrated title salt, C7H12N5S2+·Cl−·H2O, the asymmetric unit comprises one 2-amino-5-{(1E)-1-[(carbamothioylamino)imino]ethyl}-4-methyl-1,3-thiazol-3-ium cation, one chloride anion and one water molecule of crystallization. The cation is nearly flat (r.m.s. deviation of non-H atoms is 0.0814 Å), with the largest deviation of 0.1484 (14) Å observed for one of the methyl C atoms. In the crystal, the cations are linked by O—H...Cl, N—H...Cl, N—H...O, N—H...S and C—H...S hydrogen bonds, forming a tri-periodic network. The most important contributions to the crystal packing are from H...H (35.4%), S...H/H...S (24.4%), N...H/H...N (8.7%), Cl...H/H...Cl (8.2%) and C...H/H...C (7.7%) interactions.

In the title compound, C20H12N6O·C2H6OS, the [1,2,4]triazolo[1,5-a]pyridine ring system is almost planar and makes dihedral angles of 16.33 (7) and 46.80 (7)°, respectively, with the phenylamino and phenyl rings. In the crystal, molecules are linked by intermolecular N—H...O and C—H...O hydrogen bonds into chains along the b-axis direction through the dimethyl sulfoxide solvent molecule, forming C(10)R21(6) motifs. These chains are connected via S—O...π interactions, π–π stacking interactions between the pyridine rings [centroid-to-centroid distance = 3.6662 (9) Å] and van der Waals interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (28.1%), C...H/H...C (27.2%), N...H/H...N (19.4%) and O...H/H...O (9.8%) interactions.

In the title compound, C19H15N5S, the thiophene ring is disordered in a 0.6:0.4 ratio by an approximate 180° rotation of the ring around the C—C bond linking it to the pyridine ring. In the crystal, the molecules are linked by N—H...N hydrogen bonds into dimers with an R22(12) motif, forming chains along the b-axis direction. These chains are connected to each other by further N—H...N hydrogen bonds, forming a three-dimensional network. Furthermore, N—H...π and π–π [centroid–centroid separations = 3.899 (8) and 3.7938 (12) Å] interactions also contribute to the crystal cohesion. A Hirshfeld surface analysis indicated that the most important contributions to the surface contacts are from H...H (46.1%), N...H/H...N (20.4%) and C...H/H...C (17.4%) interactions.

The asymmetric unit of the title compound, C11H7N5OS, contains two independent molecules (1 and 2). The thiophene ring in molecule 2 is rotationally disordered (flip disorder) by ca 180° (around the single C—C bond, to which it is attached) over two sites with the site-occupation factors of 0.9 and 0.1. These two orientations of the thiophene ring in molecule 2 are not equivalent. In the crystal, molecules are linked by intermolecular N—H...O and N—H...N hydrogen bonds into ribbons parallel to (022) along the a axis. Within the (022) planes, these ribbons are connected by van der Waals interactions and between the (022) planes by N—H...O hydrogen bonds. In molecule 1, Hirshfeld surface analysis showed that the most important contributions to the crystal packing are from N...H/H...N (27.1%), H...H (17.6%), C...H/H...C (13.6%) and O...H/H...O (9.3%) interactions, while in molecule 2, H...H (25.4%) interactions are the most significant contributors to the crystal packing.

In the title compound, C32H29N5O2·C3H7NO, the bicyclo[3.3.1]nonane ring system adopts a half-chair/twist-boat conformation, with the phenyl rings in equatorial orientations with respect to the piperidine ring. The two oxane rings of the 2-oxabicyclo[2.2.2]octane ring system exhibit a distorted boat conformation. Intermolecular C—H...O and C—H...N hydrogen bonds connect the molecules in the crystal, generating layers extending parallel to (100). These layers are connected by C—H...π interactions. A Hirshfeld surface analysis was performed to quantify the contributions of the different intermolecular interactions, indicating that the most important contributions to the crystal packing are from H...H (52.5%), N...H/H...N (19.2%), C...H/H...C (18.8%) and O...H/H...O (8.3%) interactions.

The crystal used for structure determination contained, along with the title compound, C17H14BrN3O4, an admixture [0.0324 (11)] of its 7-bromo isomer. The 2,3-dihydro-1H-indole ring system is nearly planar, while the conformation of the 4H-pyran ring is close to a flattened boat. The mean planes of these fragments form a dihedral angle of 86.67 (9)°. The carboxylate group lies near the plane of 4H-pyran, its orientation is stabilized by an intramolecular C—H...O contact. In the crystal, the molecules are connected into layers by N—H...N and N—H...O hydrogen bonds. The most important contributions to the crystal packing are from H...H (33.1%), O...H/H...O (16.3%), N...H/H...N (12.1%), Br...H/H...Br (11.5%) and C...H/H...C (10.6%) interactions.

In the title compound, C19H13BrN2O, the pyridine ring is essentially planar [maximum deviation = 0.024 (4) Å for the N atom] and makes dihedral angles of 74.6 (2) and 65.8 (2)°, respectively, with the phenyl and bromophenyl rings, which subtend a dihedral angle of 63.1 (2)°. In the crystal, molecules are connected along the c-axis direction via C—Br...π interactions, generating zigzag chains parallel to the (010) plane. C—H...N and C—H...O hydrogen-bonding interactions further connect the molecules, forming a three-dimensional network and reinforcing the molecular packing. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (36.2%), C...H/H...C (21.6%), N...H/H...N (12.2%), and Br...H/H...Br (10.8%) interactions.

In 2-amino-4-(4-bromophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile hemihydrate, C18H14BrN3O·0.5H2O, (I), pairs of molecules are linked by pairs of N—H...N hydrogen bonds, forming dimers with an R22(12) ring motif. The dimers are connected by N—H...Br and O—H...O hydrogen bonds, and C—Br...π interactions, forming layers parallel to the (010) plane. 1,6-Diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile, C13H9N5O, (II), crystallizes in the triclinic space group P\overline{1} with two independent molecules (IIA and IIB) in the asymmetric unit. In the crystal of (II), molecules IIA and IIB are linked by intermolecular N—H...N and N—H...O hydrogen bonds into layers parallel to (001). These layers are connected along the c-axis direction by weak C—H...N contacts. C—H...π and C—N...π interactions connect adjacent molecules, forming chains along the a-axis direction. In (I) and (II), the stability of the packing is ensured by van der Waals interactions between the layers. In (I), Hirshfeld surface analysis showed that the most important contributions to the crystal packing are from H...H (37.9%), C...H/H...C (18.4%), Br...H/H...Br (13.3%), N...H/H...N (11.5%) and O...H/H...O (10.0%) interactions, while in (II), H...H interactions are the most significant contributors to the crystal packing (27.6% for molecule IIA and 23.1% for molecule IIB).

The whole molecule of the title compound, C22H19NO2, is generated by twofold rotational symmetry. The N atom exhibits a trigonal-planar geometry and is located on the twofold rotation axis. In the crystal, molecules are linked by C—H...O contacts with R22(12) ring motifs, and C—H...π interactions, resulting in ribbons along the c-axis direction. van der Waals interactions between these ribbons consolidate the molecular packing. Hirshfeld surface analysis indicates that the greatest contributions to the crystal packing are from H...H (45.5%), C...H/H...C (38.2%) and O...H/H...O (16.0%) interactions.

The molecular conformation of the title compound, C20H15Cl2N3O2, is stabilized by an intramolecular O—H...O hydrogen bond, forming an S(6) ring motif. The central pyridine ring is almost planar [maximum deviation = 0.074 (3) Å]. It subtends dihedral angles of 86.10 (15) and 87.17 (14)°, respectively, with the phenyl and dichlorophenyl rings, which are at an angle of 21.28 (15)° to each other. The =C(—OH)CH3 group is coplanar. In the crystal, molecules are linked by intermolecular N—H...N and C—H...N hydrogen bonds, and N—H...π and C—H...π interactions, forming a three-dimensional network. The most important contributions to the crystal packing are from H...H (33.1%), C...H/H...C (22.5%), Cl...H/H...Cl (14.1%), O...H/H...O (11.9%) and N...H/H...N (9.7%) interactions.

The molecular conformation of the title compound, C17H14ClN3O4, is stabilized by an intramolecular C—H...O contact, forming an S(6) ring motif. In the crystal, the molecules are connected by N—H...O hydrogen-bond pairs along the b-axis direction as dimers with R22(8) and R22(14) ring motifs and as ribbons formed by intermolecular C—H...N hydrogen bonds. There are weak van der Waals interactions between the ribbons. The most important contributions to the surface contacts are from H...H (34.9%), O...H/H...O (19.2%), C...H/H...C (11.9%), Cl...H/H...Cl (10.7%) and N...H/H...N (10.4%) interactions, as concluded from a Hirshfeld surface analysis.

In the title compound, C22H17N5·CH4O, the imidazolidine ring of the 1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine ring system is a twisted envelope, while the 1,2,3,4-tetrahydropyridine ring adopts a twisted boat conformation. In the crystal, pairs of molecules are linked by O—H...N and N—H...O hydrogen bonds via two methanol molecules, forming a centrosymmetric R44(16) ring motif. These motifs are connected to each other by C—H...N hydrogen bonds and form columns along the a axis. The columns form a stable molecular packing, being connected to each other by van der Waals interactions. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H...H (43.8%), N...H/H...N (31.7%) and C...H/H...C (18.4%) contacts.

In the title compound, C16H15N5, the 1,4-dihydropyridine ring has a shallow boat conformation, while the 1,3-diazinane ring adopts an envelope conformation. In the crystal, pairwise N—H...N hydrogen bonds generate centrosymmetric dimers featuring R22(12) motifs and C—H...N contacts connect these dimers to form double layers lying parallel to (001). Weak C—H...π and N—H...π interactions help to consolidate the double layers and van der Waals interactions occur between layers. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H...H (38.5%), N...H/H...N (33.3%) and C...H/H...C (27.3%) contacts.

In the molecular structure of the title compound, C16H13Cl2N5, the 1,4-dihydropyridine ring of the 1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine ring system adopts a screw-boat conformation, while the 1,3-diazinane ring is puckered. In the crystal, intermolecular N—H...N and C—H...N hydrogen bonds form molecular sheets parallel to the (110) and (\overline{1}10) planes, crossing each other. Adjacent molecules are further linked by C—H...π interactions, which form zigzag chains propagating parallel to [100]. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from N...H/H...N (28.4%), H...H (24.5%), C...H/H...C (21.4%) and Cl...H/H...Cl (16.1%) contacts.

In the title compound, C25H22N2O3S·0.04H2O, the central cyclohexane ring adopts a chair conformation. In the crystal, molecules are linked by N—H...O, C—H...O, and C—H...N hydrogen bonds, forming the molecular layers parallel to the bc plane, which interact by the van der Waals forces between them. A Hirshfeld surface analysis indicates that the contributions from the most prevalent interactions are H...H (41.2%), C...H/H...C (20.3%), O...H/H...O (17.8%) and N...H/H...N (10.6%).

In the title compound, C28H21N3O, the 1,2-dihydropyridine ring of the 1,2,7,8-tetrahydroisoquinoline ring system is planar as expected, while the cyclohexa-1,3-diene ring has a twist-boat conformation, with Cremer–Pople parameters QT = 0.367 (2) A, θ = 117.3 (3)° and φ = 327.3 (4)°. The dihedral angles between the best planes through the isoquinoline ring system and the three phenyl rings are 81.69 (12), 82.45 (11) and 47.36 (10)°. In the crystal, molecules are linked via N—H...O and C—H...N hydrogen bonds, forming a three-dimensional network. Furthermore, the crystal packing is dominated by C—H...π bonds with a strong interaction involving the phenyl H atoms. The role of the intermolecular interactions in the crystal packing was clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (46.0%), C...H/H...C (35.1%) and N...H/H...N (10.5%) contacts.

In the title compound, C32H28N2O, the imidazolidine and pyridine rings of the central hexahydroimidazo[1,2-a]pyridine ring system adopt envelope and screw-boat conformations, respectively. The molecule exhibits two weak intramolecular π–π interactions between phenyl rings. In the crystal, molecules are linked via pairs of C—H... O hydrogen bonds, forming inversion dimers. The dimers are further linked by pairs of C—H...π interactions, forming infinite chains along the c-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (73.4%), C...H/H...C (18.8%) and O...H/H...O (5.7%) contacts. The contribution of some disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015). Acta Cryst. C71, 9–18] in PLATON. The solvent contribution was not included in the reported molecular weight and density.

In the title compound, C25H20O2, the central cyclohexenone ring adopts an envelope conformation. The mean plane of the cyclohexenone ring makes dihedral angles of 87.66 (11) and 23.76 (12)°, respectively, with the two attached phenyl rings, while it is inclined by 69.55 (11)° to the phenyl ring of the benzoyl group. In the crystal, the molecules are linked by C—H...O and C—H...π interactions, forming a three-dimensional network.

We report an unprecedented multicomponent reaction of acetoacetanilide with malononitrile leading to a structurally novel bicyclic product (9) in a high yield. The structure has been confirmed by X-ray crystallography and comparative Hirshfeld surface analysis of 5-cyano-2-hydroxy-2-methyl-N-phenyl-4-(yridine-4-yl)-6-(thiophen-2-yl)-3,4-dihydro-2H-pyran-3-carboxamide 2, 5-cyano-2-hydroxy-2-methyl-6-oxo-N-phenyl-4-(thiophen-2-yl)piperidine-3-carboxamide 4 and 2-(8-amino-7,8a-dicyano-1-imino-4a-methyl-3-oxo-2-phenyl-1,3,4,4a,5,8a-hexahydroisoquinolin-6(2H)-ylidene)-N-phenylacetamide 9.