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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)R 2 1(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 R 2 2(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.

In the polymeric title compound, {[Na(C10H9N4O4S)(H2O)3]·2H2O} n , sixfold coordinated Na+ cations are linked into a chain parallel to [010] by sharing common water molecules. Next to the four bridging water molecules, each Na+ cation of the chain is bonded to the O atom of a terminal water molecule and an O atom of the SO3 − group of the sulfonate anion. Classical O—H...O, O—H...N and N—H...O hydrogen bonds and additional π–π interactions connect these chains into a three-dimensional network.

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, C20H26O5, the two cyclohexane rings adopt boat and half-chair conformations. In the crystal, adjacent molecules are connected by intermolecular C—H...O hydrogen bonds, forming a three-dimensional network. According to a Hirshfeld surface study, H...H interactions are the most significant contributors to the crystal packing (63.0%).

In the title compound, C31H44O5, molecules are connected by O—H...O and C—H...O hydrogen bonds, forming hydrogen-bonded zigzag chains running along the b axis and parallel to the (001) plane. The molecular packing is stabilized by van der Waals interactions between these chains along the a and c axes. The intermolecular interactions in the crystal structure were quantified and analysed using Hirshfeld surface analysis.

The crystal structures and Hirshfeld surface analyses of three salts of 1-(4-nitrophenyl)piperazine with 2-chlorobenzoic acid, 2-bromobenzoic acid and 2-iodobenzoic acid are reported. The chlorobenzoate salt, C10H14N3O2 +·C7H4ClO2 −, contains whole-ion-disordered cations and anions, which were modeled with two equivalent conformations with occupancies of 0.745 (10)/0.255 (10) and 0.563 (13)/0.437 (13), respectively. The bromobenzoate and iodobenzoate derivatives are isomorphous and crystallize as hemihydrates, viz. C10H14N3O2 +·C7H4BrO2 −·0.5H2O and C10H14N3O2 +·C7H4IO2 −·0.5H2O, respectively [the water molecule is disordered over two locations with occupancies of 0.276 (3)/0.223 (3) for the iodobenzoate derivative]. In the extended structures, all three salts feature an R 4 4(12) loop of two anions and two cations linked by N—H...O hydrogen bonds.

The title compound, C20H21F3N2O4, features a main twelve-membered difuryl ring with which the furan rings make dihedral angles of 76.14 (5) and 33.81 (5)°. The dihedral angle between the furan rings is 42.55 (7)°. The six-membered nitrogen heterocycle has a twist-boat conformation. In the crystal, pairs of molecules are connected by intermolecular C—H...O interactions, generating an R 2 2(14) ring motif. These pairs of molecules form zigzag chains along the a-axis direction by means of C—H...F interactions. Furthermore, C—H...π and C–F...π interactions link the molecules into chains along the b-axis direction, forming sheets parallel to the (001) plane. These sheets are also connected by van der Waals interactions.

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.

In the title compound, C23H25F4NO3, the 1,4-dihydropyridine ring adopts a distorted boat conformation, while the cyclohexene ring is almost showing a half-chair conformation. In the crystal, intermolecular N—H...O hydrogen bonds connect the molecules into chains with graph-set motif C(6) parallel to the a-axis. These chains are linked together by C—H...O and C—H...F interactions, forming a three-dimensional network. In addition, C—H...π interactions link the molecules into layers parallel to the (100) plane. A Hirshfeld surface analysis was performed to further investigate the intermolecular 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.

The molecule of the title compound, C14H8Br3N3O2, consists of three almost planar groups: the central dibromoethenyldiazene fragment and two attached aromatic rings. The mean planes of these rings form dihedral angles with the plane of the central fragment of 26.35 (15) and 72.57 (14)° for bromine- and nitro-substituted rings, respectively. In the crystal, C—H...Br interactions connect molecules, generating zigzag C(8) chains along the [100] direction. These chains are linked by C—Br...π interactions into layers parallel to (001). van der Waals interactions between the layers aid in the cohesion of the crystal packing. The most substantial contributions to crystal packing, according to a Hirshfeld surface analysis, are from Br...H/H...Br (20.9%), C...H/H...C (15.2%), O...H/H...O (12.6%) and H...H (11.7%) contacts.

The title compound, C20H24BrNO2, is chiral at the carbon atoms on either side of the oxygen atom of the oxazolidine ring and crystallizes as a racemate. The 1,3-oxazolidine ring adopts an envelope conformation with the N atom in an endo position. The mean plane of the oxazolidine ring makes dihedral angles of 77.74 (10) and 45.50 (11)°, respectively, with the 4-bromophenol and 1,3,5-trimethylbenzene rings. In the crystal, adjacent molecules are connected via C—H...O hydrogen bonds and C—H...π interactions into layers parallel to the (200) plane. The packing is strengthened by van der Waals interactions between parallel molecular layers. A Hirshfeld surface analysis shows that H...H (58.2%), C...H/H...C (18.9%), and Br...H/H...Br (11.5%) interactions are the most abundant in the crystal packing.

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 R 2 2(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.

In the title compound, C14H8Br2FN3O2, the 4-fluorophenyl ring and the nitro-substituted phenyl ring form a dihedral angle of 64.37 (10)°. Molecules in the crystal are connected by C—H...O and C—H...F hydrogen bonds into layers parallel to (011). The crystal packing is consolidated by C—Br...π and C—F...π interactions, as well as by π–π stacking interactions. According to a Hirshfeld surface analysis of the crystal structure, the most significant contributions to the crystal packing are from O...H/H...O (15.0%), H...H (14.3%), Br...H/H...Br (14.2%), C...H/H...C (10.1%), F...H/H...F (7.9%), Br...Br (7.2%) and Br...C/C...Br (5.8%) contacts.

The title compound, 2C16H27NO·H2O, crystallizes in the monoclinic P21/c space group with two independent molecules (A and B) in the asymmetric unit. In the crystal, molecules A and B are linked through the water molecules by intermolecular O—H...O and O—H...N hydrogen bonds, producing chains along the b-axis direction. These chains are linked with neighboring chains parallel to the (103) plane via C—H...π interactions, generating ribbons along the b-axis direction. The stability of the molecular packaging is ensured by van der Waals interactions between the ribbons. According to the Hirshfeld surface study, H...H interactions are the most significant contributors to the crystal packing (80.3% for molecule A and 84.8% for molecule B).

In the title molecule, C25H28N2O5S, (alternative name ethyl 2-{[7-acetyl-4-cyano-6-hydroxy-8-(4-methoxyphenyl)-1,6-dimethyl-5,6,7,8-tetrahydroisoquinolin-3-yl]sulfanyl}acetate) the 4-methoxyphenyl group is disposed on one side of the bicyclic core and the oxygen atoms of the hydroxyl and acetyl groups are disposed on the other side. In the crystal, a layered structure parallel to the ac plane is generated by O—H...O and C—H...O hydrogen bonds plus C—H...π(ring) interactions.

The asymmetric unit of the title compound, C25H21N3O2S, comprises four molecules. Their conformations differ primarily in the orientations of the styryl and the N-phenylcarboxamido groups. In the crystal, intermolecular N-H center dot center dot center dot N, C-H center dot center dot center dot O and C-H center dot center dot center dot S hydrogen-bonding contacts as well a C-H center dot center dot center dot pi(ring) interactions lead to the formation of a layer structure parallel to (010). Hirshfeld surface analysis revealed that H center dot center dot center dot H interactions represent the main contributions to the crystal packing.

TARAMAWOS WOS:000760208800003 TARAMAPUBMED TARAMASCOPUS The bicyclic imidazo[1,2-a]pyridine core in the molecule of the title compound, C10H7F3N2O, is planar within 0.004 (1) A ° . In the crystal, the molecules are linked by pairs of C—H N and C—H O hydrogen bonds, forming strips. These strips are connected by the F F contacts into layers, which are further joined by – stacking interactions. The Hirshfeld surface analysis and fingerprint plots reveal that molecular packing is governed by F H/H F (31.6%), H H (16.8%), C H/H C (13.8%) and O H/H O (8.5%) contacts. 1. Chemical context The imidazo[1,2-a]pyridine synthon is one of the important fused bicyclic 5–6 heterocycles and it is recognized as a ‘drug prejudice’ scaffold because of its wide range of applications in medicinal chemistry (Bagdi et al., 2015). This synthon is also useful in coordination chemistry and catalysis because of its coordination ability and non-covalent donor–acceptor bonding (Guseinov et al., 2022; Ma et al., 2020, 2021; Mahmudov et al., 2020, 2021). Synthesis of this synthon from easily available chemicals is desirable due to its importance in the various branches of chemistry (Bagdi et al., 2015). Along with this, intermolecular interactions organize molecular architectures, which play a crucial role in synthesis, catalysis, micellization, etc. (Gurbanov et al., 2020a,b; Kopylovich et al., 2011; Ma et al., 2017a,b). The non-covalent bond–acceptor ability of both nitrogen atoms in the imidazo[1,2-a]pyridine synthon can be used in crystal engineering and in the design of dyes and other materials (Maharramov et al., 2018; Mizar et al., 2012; Shixaliyev et al., 2014; Shikhaliyev et al., 2018, 2019). Herein, we report a one-pot synthesis of 2,2,2-trifluoro-1-(7- methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one (I) from (E/Z)- 3-bromo-1,1,1-trifluoro-4-isopropoxybut-3-en-2-one and 4-methylpyridin-2-amine, which provides multiple intermolecular non-covalent

In the crystal, C—H⋯N, C—Cl⋯π inter­actions and face-to-face π–π stacking inter­actions connect the mol­ecules, forming ribbons along the a-axis direction., In the title compound, C14H7Cl4FN2, the dihedral angle between the 4-fluoro­phenyl ring and the 2,4-di­chloro­phenyl ring is 46.03 (19)°. In the crystal, the mol­ecules are linked by C—H⋯N inter­actions along the a-axis direction, forming a C(6) chain. The mol­ecules are further connected by C—Cl⋯π inter­actions and face-to-face π–π stacking inter­actions, forming ribbons along the a-axis direction. Hirshfeld surface analysis indicates that the greatest contributions to the crystal packing are from Cl⋯H/H⋯Cl (35.1%), H⋯H (10.6%), C⋯C (9.7%), Cl⋯Cl (9.4%) and C⋯H/H⋯C (9.2%) inter­actions.

In the cation of the title salt, C30H28NO2 +·CF3O3S−, the four tetrahydrofuran rings adopt envelope conformations. In the crystal, pairs of cations are linked by dimeric C—H...O hydrogen bonds, forming two R 2 2(6) ring motifs parallel to the (001) plane. The cations and anions are connected by further C—H...O hydrogen bonds, forming a three-dimensional network structure. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (47.6%), C...H/H...C (20.6%), O...H/H...O (18.0%) and F...H/H...F (9.9%) interactions.

The mol­ecular conformation of the title compound is stabilized by an intra­molecular O—H⋯O hydrogen bond, forming an S(6) ring motif. Inter­molecular N—H⋯N and C—H⋯N hydrogen bonds, as well as N—H⋯π and C—H⋯π inter­actions create a three-dimensional network in the crystal., 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.

In the title compound, C15H12N2O3, pairs of molecules are linked into dimers by N-H center dot center dot center dot O hydrogen bonds, forming an R-2(2)(12) ring motif, with the dimers stacked along the a axis. These dimers are connected through pi-pi stacking interactions between the centroids of the benzene and furan rings of their 2,3-dihydro-1-benzofuran ring systems. Furthermore, there exists a C-H center dot center dot center dot pi interaction that consolidates the crystal packing. A Hirshfeld surface analysis indicates that the most important contacts are H center dot center dot center dot H (40.7%), O center dot center dot center dot H/H center dot center dot center dot O (24.7%), C center dot center dot center dot H/H center dot center dot center dot C (16.1%) and C center dot center dot center dot C (8.8%).

In the crystal, mol­ecules of the title compound are connected through C—H⋯π, C—Cl⋯π, Cl⋯Cl and Cl⋯H inter­actions, generating a three-dimensional network., In the mol­ecule of the title compound, C22H14Cl4N4, the central benzene ring makes dihedral angles of 77.03 (9) and 81.42 (9)° with the two approximately planar 2,2-di­chloro-1-[(E)-phenyl­diazen­yl]vinyl groups. In the crystal, mol­ecules are linked by C—H⋯π, C—Cl⋯π, Cl⋯Cl and Cl⋯H inter­actions, forming a three-dimensional network. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (30.4%), C⋯H/H⋯C (20.4%), Cl⋯H/H⋯Cl (19.4%), Cl⋯Cl (7.8%) and Cl⋯C/C⋯Cl (7.3%) 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 R 2 2(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).

In the title molecule, C23H20Cl2N4O3S, the thiazole ring is planar while the pyrimidine unit fused to it adopts a screw-boat conformation. In the crystal, thick sheets parallel to the bc plane are formed by N—H...N, C—H...N and C—H...O hydrogen bonds together with π–π interactions between the formamido carbonyl groups and the thiazole rings. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (30.9%), Cl...H/H...Cl (20.7%), C...H/H...C (16.8%) and O...H/H...O (11.4%) interactions.

The title compound, C29H33NO3, crystallizes with three molecules (A, B and C) in the asymmetric unit. They differ in the twist of the phenyl and benzene rings of the 1,1′-biphenyl ring with respect to the plane of the 1,4-dihydropyridine ring. In all three molecules, the 1,4-dihydropyridine ring adopts a distorted boat conformation. The cyclohexene ring has an envelope conformation in molecules A and B, while it exhibits a distorted half-chair conformation for both the major and minor components in the disordered molecule C. In the crystal, molecules are linked by C—H...O and N—H...O hydrogen bonds, forming layers parallel to (100) defining R 1 4(6) and C(7) graph-set motifs. Additional C—H...π interactions consolidate the layered structure. Between the layers, van der Waals interactions stabilize the packing, as revealed by Hirshfeld surface analysis. The greatest contributions to the crystal packing are from H...H (69.6% in A, 69.9% in B, 70.1% in C), C...H/H...C (20.3% in A, 20.6% in B, 20.3% in C) and O...H/H...O (8.6% in A, 8.6% in B, 8.4% in C) interactions.

The title molecule, C21H26N2O3, adopts a V-shaped conformation and is chiral at the C atom with methyl group attached at the common cut of the edges of the V-conformation and crystallizes as a racemate. It also contains an intramolecular O—H...N hydrogen bond. In the crystal, N—H...O hydrogen bonds form chains of molecules extending along the c-axis direction, together with normal van der Waals contacts. The roles of the various intermolecular interactions were clarified by Hirshfeld surface analysis, which reveals that the most important contributions to the crystal packing are from H...H (62.6%), C...H/H...C (15.8%) and O...H/H...O (15.3%) contacts.

The title compound, 2C12H10N6·C3H7NO, crystallizes as a racemate in the monoclinic P21/c space group with two independent molecules (I and II) and one dimethylformamide solvent molecule in the asymmetric unit. Both molecules (I and II) have chiral centers at the carbon atoms where the triazine rings of molecules I and II are attached to the phenyl ring. In the crystal, molecules I and II are linked by intermolecular N—H...N, N—H...O and C—H...N hydrogen bonds through the solvent dimethylformamide molecule into layers parallel to (001). In addition, C—H...π interactions also connect adjacent molecules into layers parallel to (001). The stability of the molecular packing is ensured by van der Waals interactions between the layers. The Hirshfeld surface analysis indicates that N...H/H...N (38.3% for I; 35.0% for II), H...H (28.2% for I; 27.0% for II) and C...H/H...C (23.4% for I; 26.3% for II) interactions are the most significant contributors to the crystal packing.

The molecule of the title compound, C24H16Cl12N2O4, is generated by a crystallographic inversion centre at the midpoint of the central C—C bond. A kink in the molecule is defined by a torsion angle of −169.86 (15)° about this central bond of the alkyl bridge. The pyrrolidine ring is essentially planar [max. deviation = 0.014 (1) Å]. The cyclohexane ring has a boat conformation, while both cyclopentane rings adopt an envelope conformation. In the crystal structure, molecules are linked by intermolecular C—H...O, C—H...Cl and C—Cl...π interactions, and short intermolecular Cl...O and Cl...Cl contacts, forming a three-dimensional network.

The styryl and ester substituents are displaced to opposite sides of the plane through the pyridine ring while the acetyl group is rotated well out of that plane. In the crystal, inversion-related C—H⋯O hydrogen bonds form chains extending parallel to the a-axis direction, which pack with partial inter­calation of the styryl and ester substituents., In the title mol­ecule, C21H20N2O3S, the styryl and ester substituents are displaced to opposite sides of the plane of the pyridine ring. In the crystal, C—H⋯O hydrogen bonds form chains extending parallel to the a-axis direction, which pack with partial inter­calation of the styryl and ester substituents. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H⋯H (43.6%), C⋯H/H⋯C (15.6%), O⋯H/H⋯O (14.9%) and N⋯H/H⋯N (11.2%) contacts.

In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds into ribbons along the c-axis direction. The layered crystal packing is further consolidated by van der Waals and C—H⋯π inter­actions., In the crystal, the whole mol­ecule of the title compound, C14H12N4O7·0.224H2O, is nearly planar with a maximum deviation from the least-squares plane of 0.352 (1) Å. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal, mol­ecules are linked by centrosymmetric pairs of N—H⋯O hydrogen bonds, forming ribbons along the c-axis direction. These ribbons connected by van der Waals contacts, forming sheets parallel to the ac plane. There are also inter­molecular van der Waals contacts and and C—H⋯π inter­actions between the sheets. A Hirshfeld surface analysis indicates that the most prevalent inter­actions are O⋯H/H⋯O (41.2%), H⋯H (19.2%), C⋯H/H⋯C (12.2%) and C⋯O/ O⋯C (8.4%).

The conformation of the title compound is partially determined by a strong, intra­molecular O—H⋯O hydrogen bond. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules, forming chains along the a-axis direction, which are linked into strongly corrugated sheets parallel to the ac plane by C—H⋯O hydrogen bonds and C—H⋯π(ring) inter­actions. The sheets are associated through additional C—H⋯π(ring) inter­actions., The conformation of the title compound, C13H11NO2, is partially determined by a strong, intra­molecular O—H⋯O hydrogen bond. The crystal packing consists of strongly corrugated layers parallel to the ac plane and associated through C—H⋯π(ring) inter­actions. A Hirshfeld surface analysis of the crystal structure indicates that the most significant contributions to the crystal packing are from H⋯H (44.1%), C⋯H/H⋯C (29.4%) and O⋯H/H⋯O (17.3%) 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 center dot center dot center dot N hydrogen bonds generate centrosymmetric dimers featuring R-2(2)(12) motifs and C-H center dot center dot center dot N contacts connect these dimers to form double layers lying parallel to (001). Weak C-H center dot center dot center dot pi and N-H center dot center dot center dot pi interactions help to consolidate the double layers and van derWaals interactions occur between layers. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H center dot center dot center dot H (38.5%), N center dot center dot center dot H/H center dot center dot center dot N (33.3%) and C center dot center dot center dot H/H center dot center dot center dot C (27.3%) contacts.

In the crystal, O—H⋯N and N—H⋯O hydrogen bonds link pairs of mol­ecules via two methanol mol­ecules. These mol­ecules are connected to each other by C—H⋯N hydrogen bonds and form columns along the a-axis direction., 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 R 4 4(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.

The molecule of the title compound, C15H15Br2NO3, comprises a fused tricyclic system consisting of two five-membered rings (cyclopentane and tetrahydrofuran) and one six-membered ring (tetrahydropyridinone). Both five-membered rings of the tricyclic system have envelope conformations, and the conformation of the six-membered cycle is intermediate between chair and half-chair. In the crystal, the molecules are linked by C-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi, C-Br center dot center dot center dot pi and C center dot center dot center dot O interactions into double layers. The layers are connected into a three-dimensional network by van der Waals interactions.

The relative conformations about the three chiral carbon atoms are established. The two fused five-membered rings and their N-bound aromatic substituents form a pincer-like motif. In the crystal, a combination of C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π(ring) inter­actions leads to the formation of layers parallel to the bc plane with the di­phenyl­pyrrole groups protruding from both sides of the layers., In the title compound, C33H26N4O4, the two fused five-membered rings and their N-bound aromatic substituents form a pincer-like motif. The relative conformations about the three chiral carbon atoms are established. In the crystal, a combination of C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π(ring) inter­actions leads to the formation of layers parallel to the bc plane. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H⋯H (44.3%), C⋯H/H⋯C (29.8%) and O⋯H/H⋯O (15.0%) contacts.

Özçelik, Nefise Dilek ( Aksaray, Yazar ), In the title compound, C24H20ClNO2, the mean planes of 4-chlorophenyl, 2-methylphenyl and phenylene rings make dihedral angles of 62.8 (2), 65.1 (3) and 15.1 (2)°, respectively, with the 5-methyl-1,2-oxazole ring. In the crystal, molecules are linked by intermolecular C-H⋯N, C-H⋯Cl, C-H⋯π contacts and π-π stacking interactions between the phenylene groups. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (48.7%), H⋯C/C⋯H (22.2%), Cl⋯H/H⋯Cl (8.8%), H⋯O/O⋯H (8.2%) and H⋯N/N⋯H (5.1%) interactions. © 2021 International Union of Crystallography. All rights reserved.

The asymmetric units of compounds I and II both consist of two independent mol­ecules. In the crystal of I, mol­ecules are linked through N—H⋯O hydrogen bonds, forming inversion dimers with (8) ring motifs and with their mol­ecular planes parallel to (020). C—H⋯O inter­actions connect the dimers, forming a three-dimensional network. In the crystal of II, mol­ecules are linked by C—H⋯N, C—H⋯O and C—H⋯π inter­actions, resulting in a three-dimensional network., In the title compounds C23H21ClN2O3 [I, namely 1-(4-chloro­phen­yl)-4-(4-methyl­phen­yl)-3,8-dioxo-1,2,5,6,7,8-hexa­hydro­quine-3-carb­oxy­lic acid] and C24H22N2O3 [II, namely 4-(4-meth­oxy­phen­yl)-1-(4-methyl­phen­yl)-2,5-dioxo-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile], each of the cyclo­hexene and di­hydro­pyridine rings of the 1,2,5,6,7,8-hexa­hydro­quinoline moieties adopts a twisted-boat conformation. The asymmetric units of both compounds I and II consist of two independent mol­ecules (A and B). In II A, three carbon atoms of the cyclo­hexene ring are disordered over two sets of sites in a 0.670 (11):0.330 (11) occupancy ratio. In the crystal of I, mol­ecules are linked through classical N—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif and with their mol­ecular planes parallel to the crystallographic (020) plane. Non-classical C—H⋯O hydrogen-bonding inter­actions connect the dimers, resulting in a three-dimensional network. In the crystal of II, mol­ecules are linked by C—H⋯N, C—H⋯O and C—H⋯π inter­actions, forming a three-dimensional network.

The mol­ecular and crystal structures of (I), C20H19N3O2, and (II), C22H21N3O, are similar because they differ only in the substituent at the hydrazide N atom where a phenyl­methyl­ene moiety for (II) is present instead of a furan­methyl­ene moiety for (I)., The conformation about the central benzene ring in the mol­ecule of (I), C20H19N3O2, is partially determined by an intra­molecular N—H⋯O hydrogen bond. In the crystal, chains parallel to the c axis are generated by inter­molecular N—H⋯O hydrogen bonds with the chains assembled into a three-dimensional network structure by inter­molecular C—H⋯O hydrogen bonds and C—H⋯π(ring) inter­actions. The mol­ecule of (II), C22H21N3O, differs from (I) only in the substituent at the hydrazide N atom where a phenyl­methyl­ene moiety for (II) is present instead of a furan­methyl­ene moiety for (I). Hence, mol­ecules of (I) and (II) show similarities in their mol­ecular and crystal structures. The conformation of the central portion of the mol­ecule of (II) is also therefore partially determined by an intra­molecular N—H⋯O hydrogen bond and inter­molecular N—H⋯O hydrogen bonds form chains parallel to the c axis. Likewise, the chains are connected into a three-dimensional network by C—H⋯O hydrogen bonds and C—H⋯π(ring) inter­actions.

The title compound crystallizes with two independent mol­ecules in the asymmetric unit. In the crystal, strong inter­molecular O—H⋯O hydrogen bonds and weak inter­molecular C—H⋯O contacts link the mol­ecules, forming a three-dimensional network. In addition, weak π–π stacking inter­actions are observed., The title compound, C24H24N2O5S, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. In the central ring systems of both mol­ecules, the tetra­hydro­furan rings adopt envelope conformations, the pyrrolidine rings adopt a twisted-envelope conformation and the six-membered ring is in a boat conformation. In mol­ecules A and B, the nine-membered groups attached to the central ring system are essentially planar (r.m.s. deviations of 0.002 and 0.003 Å, respectively). They form dihedral angles of 64.97 (9) and 56.06 (10)°, respectively, with the phenyl rings. In the crystal, strong inter­molecular O—H⋯O hydrogen bonds and weak inter­molecular C—H⋯O contacts link the mol­ecules, forming a three-dimensional network. In addition weak π–π stacking inter­actions [centroid-to centroid distance = 3.7124 (13) Å] between the pyrrolidine rings of the nine-membered groups of A mol­ecules are observed. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to qu­antify the inter­molecular inter­actions present in the crystal, indicating that the environments of the two mol­ecules are very similar. The most important contributions for the crystal packing are from H⋯H (55.8% for mol­ecule A and 53.5% for mol­ecule B), O⋯H/H⋯O (24.5% for mol­ecule A and 26.3% for mol­ecule B) and C⋯H/H⋯C (12.6% for mol­ecule A and 15.7% for mol­ecule B) inter­actions.

The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond between the hy­droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit., In the title compound, C27H33NO5, a 3,3,6,6-tetra­methyl­tetra­hydro­acridine-1,8-dione ring system carries an ethyl acetate substituent on the acridine N atom and an o-hy­droxy­phenyl ring on the central methine C atom of the di­hydro­pyridine ring. The benzene ring is inclined to the acridine ring system at an angle of 80.45 (7)° and this conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond between the hy­droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit. The ester C=O oxygen atom is disordered over major and minor orientations in a 0.777 (9):0.223 (9) ratio and the terminal –CH3 unit of the ethyl side chain is disordered over two sets of sites in a 0.725 (5): 0.275 (5) ratio. In the crystal, C—H⋯O hydrogen bonds combine to link the mol­ecules into a three-dimensional network. van der Waals H⋯H contacts contribute the most to the Hirshfeld surface (66.9%) followed by O⋯H/H⋯O (22.1%) contacts associated with weak hydrogen bonds.

In the title compound, C15H15Br2NO2, two bridged tetrahydrofuran rings adopt envelope conformations with the O atom as the flap. The pyrrolidine ring also adopts an envelope conformation with the spiro C atom as the flap. In the crystal, the molecules are linked into dimers by pairs of C—H...O hydrogen bonds, thus generating R 2 2(18) rings. The crystal packing is dominated by H...H, Br...H, H...π and Br...π interactions. One of the Br atoms is disordered over two sites with occupation ratio of 0.833 (8):0.167 (8).

In the crystal, the molecule of the title compound, C26H20N2O3, has crystallographically imposed twofold rotation symmetry. The crystal packing consists of layers parallel to the ab plane formed by O—H...N and C—H...O hydrogen bonds. Between the layers, C—H...π interactions are observed.

The supra­molecular structure of the compound is stabilized by a three-dimensional array of N—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π inter­actions., 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 Q T = 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 crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming sheets lying parallel to the (002) plane. These sheets are connected only by weak van der Waals inter­actions., The title compound, C15H15Br2NO2, crystallizes with two mol­ecules in the asymmetric unit of the unit cell. In both mol­ecules, the tetra­hydro­furan rings adopt an envelope conformation with the O atom as the flap and the pyrrolidine rings adopt an envelope conformation. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming sheets lying parallel to the (002) plane. These sheets are connected only by weak van der Waals inter­actions. The most important contributions to the surface contacts are from H⋯H (44.6%), Br⋯H/H⋯Br (24.1%), O⋯H/H⋯O (13.5%) and C⋯H/H⋯C (11.2%) inter­actions, as concluded from a Hirshfeld surface analysis.

In the title compound, C20H19NO5, the central six-membered ring has a slightly distorted half-chair conformation, with puckering parameters of Q(T) = 0.3387 (11) angstrom, theta = 49.11 (19)degrees and phi = 167.3 (2)degrees. The conformation of the fused pyrrolidine ring is that of an envelope. Molecules are connected by intermolecular C-H center dot center dot center dot O hydrogen bonds, C-H center dot center dot center dot pi interactions and pi-pi stacking interactions [centroid-to-centroid distance = 3.9536 (11) angstrom, with a slippage of 2.047 angstrom], forming a three-dimensional network. The most important contributions to the surface contacts are from H center dot center dot center dot H (46.3%), O center dot center dot center dot H/H center dot center dot center dot O (31.5%) and C center dot center dot center dot H/H center dot center dot center dot C (17.3%) interactions, as concluded from a Hirshfeld surface analysis.

In the title compound, inter­molecular C—H⋯π inter­actions and π–π stacking inter­actions help to stabilize the crystal structure, forming a three-dimensional network., The title compound, C22H33N3O4, crystallizes in the triclinic space group P with two mol­ecules in a unit cell. The two pyrrole rings are essentially planar (r.m.s. deviation = 0.002 Å) and they form a dihedral angle of 81.24 (10)° with each other. The crystal packing is stabilized by C—H⋯π inter­actions and π–π stacking inter­actions, forming a three-dimensional network. The Hirshfeld surface analysis and two-dimensional fingerprint plots reveal that the most important contributions for the crystal packing are from H⋯H (74.3%), C⋯H/H⋯C (11.5%) and O⋯H/H⋯O (9.1%) contacts.

The title compound, C11H8N4OS, crystallizes with two independent molecules in the asymmetric unit. In the crystal, the N-H center dot center dot center dot N and C-H center dot center dot center dot N hydrogen bonds connect the molecules, generating double layers parallel to the (001) plane. The layers are joined by C-H center dot center dot center dot pi interactions to form a three-dimensional supramolecular structure.

In the title compound, C14H8Br2FN3O2, the nitro-substituted benzene ring and the 4-fluorophenyl ring form a dihedral angle of 65.73 (7)degrees. In the crystal, molecules are linked into chains by C-H center dot center dot center dot O hydrogen bonds running parallel to the c-axis direction. The crystal packing is consolidated by C-F center dot center dot center dot pi interactions and pi-pi stacking interactions, and short Br center dot center dot center dot O [2.9828 (13) angstrom] contacts are observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H center dot center dot center dot H (17.4%), O center dot center dot center dot H/H center dot center dot center dot O (16.3%), Br center dot center dot center dot H/H center dot center dot center dot Br (15.5%), Br center dot center dot center dot C/C center dot center dot center dot Br (10.1%) and F center dot center dot center dot H/H center dot center dot center dot F (8.1%) contacts.