Crystal structure of (E)-N-(3,4-di-meth-oxy-benzyl-idene)morpholin-4-amine.

In the title compound, C13H18N2O3, the benzene ring makes a dihedral angle of 17.19 (11)° with the least-squares plane formed by the four C atoms of the morpholine ring, which adopts a chair conformation. In the crystal, C-H⋯N hydrogen bonds link the mol-ecules into supramolecular chains running along a 21 screw axis parallel to the b-axis direction. Weak C-H⋯π inter-actions are also observed.

Crystal structure of {(E)-4-[(1-allyl-1H-1,2,3-triazol-4-yl)meth-oxy]benzyl-idene}[2-(morpholin-4-yl)eth-yl]amine.

In the title compound, C19H25N5O2, the morpholine ring has a chair conformation. The plane of the central benzene ring makes dihedral angles of 88.75 (12) and 60.02 (7)°, respectively, with the mean plane formed by the four planar C atoms of the morpholine ring and with the plane of the triazole ring. In the crystal, mol-ecules are linked via C-H⋯π inter-actions, forming slabs lying parallel to (10-1). The C atoms of the bridging ethyl-ene group, between the morpholine and benzene rings, and the terminal ethene group of the prop-1-ene substituent attached to the triazole ring, are disordered over two sets of sites, with an occupancy ratio of 0.634 (13):0.366 (13).

Synthesis, crystal structure and Hirshfeld surface analysis of (3Z)-4-[(4-amino-1,2,5-oxa-diazol-3-yl)amino]-3-bromo-1,1,1-tri-fluoro-but-3-en-2-one.

In the title compound, C6H4BrF3N4O2, the oxa-diazole ring is essentially planar with a maximum deviation of 0.003 (2) Å. In the crystal, mol-ecular pairs are connected by N-H⋯N hydrogen bonds, forming dimers with an R 2 2(8) motif. The dimers are linked into layers parallel to the (10) plane by N-H⋯O hydrogen bonds. In addition, C-O⋯π and C-Br⋯π inter-actions connect the mol-ecules, forming a three-dimensional network. The F atoms of the tri-fluoro-methyl group are disordered over two sites in a 0.515 (6): 0.485 (6) ratio. The inter-molecular inter-actions in the crystal structure were investigated and qu-anti-fied using Hirshfeld surface analysis.

5-Fluoro-3-phenyl-N'-(4-propyl-cyclo-hexyl-idene)-1H-indole-2-carbohydrazide.

In the title compound, C24H26FN3O, the cyclo-hexane ring adopts a chair conformation; the propyl substituent is in an equatorial orientation and the bond-angle sum at the C atom bonded to the carbohydrazide N atom is 360.0°. The dihedral angle between the 1H-indole ring system and the phenyl ring is 82.77 (13)°. A weak intra-molecular C-H⋯π contact occurs. In the crystal, pairs of mol-ecules related by a crystallographic twofold axis are linked by bifurcated N-H⋯(O,N) hydrogen bonds; a C-H⋯O inter-action occurs between the same pair. The dimers are linked by C-H⋯F and C-H⋯π inter-actions, generating a three-dimensional network.

5-Fluoro-N'-(4-methyl-cyclo-hexyl-idene)-3-phenyl-1H-indole-2-carbohydrazide.

The title compound, C22H22FN3O, crystallized with two independent mol-ecules (A and B) in the asymmetric unit; these are linked by a pair of N-H⋯O hydrogen bonds, forming a pseudo-centrosymmetric dimer with an R (2) 2(10) motif. In addition, a number of C-H⋯π inter-actions are also observed. The 1H-indole ring systems in mol-ecules A and B are essentially planar [maximum deviations of 0.019 (2) and 0.014 (2) Å, respectively] and make dihedral angles of 77.64 (10) and 69.50 (9)°, respectively, with thephenyl rings.

5-Fluoro-N-(2-methyl-3-oxo-1-thia-4-aza-spiro-[4.5]dec-4-yl)-3-phenyl-1H-indole-2-carboxamide.

In the title compound, C24H24FN3O2S, the 1,3-thia-zolidine ring adopts an envelope conformation with the S atom as the flap, while the cyclo-hexane ring is in a chair conformation. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯F hydrogen bonds, forming a three-dimensional network. The unit cell contains six voids of 57 Å(3), but the residual electron density (highest peak = 0.23 e Å(-3) and deepest hole = -0.19 e Å(-3)) in the difference Fourier map suggests no solvent mol-ecule occupies this void.

N'-(4-Ethyl-cyclo-hexyl-idene)-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide.

The title compound, C23H24FN3O, crystallizes with two independent mol-ecules (I and II) in the asymmetric unit. These pairs of mol-ecules are linked to each other as N-H⋯O dimers with an R 2 (2)(10) motif. Furthermore, the crystal structure also exhibits C-H⋯π inter-actions. The atoms of the ethyl group in mol-ecule I are disordered over two sites with an occupancy ratio of 0.817 (6):0.183 (6).

Crystal structure and Hirshfeld surface analysis of bis-{(Z)-N'-[(E)-(furan-2-yl)methyl-idene]carbamo-hydrazono-thio-ato}nickel(II) methanol disolvate.

In the title complex, [Ni(C6H6N3OS)2]·2CH3OH, the NiII atom is coordinated by the S and N atoms of two N'-[(Z)-(furan-2-yl)methyl-idene]carbamohydrazono-thioic acid ligands in a distorted square-planar geometry. The two mutual ligands bound to NiII are also connected by C-H⋯S inter-actions, while the H atoms of the NH2 group of the ligands form R 4 4(8) motifs with the O atoms of the solvent ethyl alcohol mol-ecules. At the same time, the OH groups of the solvent ethyl alcohol mol-ecules form parallel layers to the (011) plane by the O-H⋯N inter-actions with the ligand N atom that is not bonded to the NiII atom.. The layers are connected by van der Waals inter-actions. A Hirshfeld surface analysis indicates that the most important contacts are H⋯H (37.7%), C⋯H/H⋯C (14.6%), O⋯H/H⋯O (11.5%) and S⋯H/H⋯S (10.6%).

Synthesis, crystal structure and Hirshfeld surface analysis of 5-[2-(di-cyano-methyl-idene)hydrazin-1-yl]-2,4,6-tri-iodo-isophthalic acid ethanol monosolvate.

The title compound, C11H3I3N4O4·C2H6O, crystallizes in the triclinic P space group with one independent mol-ecule and one ethanol solvent mol-ecule in the asymmetric unit. The benzene ring and the methyl-carbonohydrazonoyl dicyanide group of the main mol-ecule makes a dihedral angle of 57.91 (16)°. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link pairs of mol-ecules, forming dimers with R 2 2(14) motifs. These dimers are connected by O-H⋯O hydrogen bonds into chains along the a-axis direction, forming R 2 2(16) ring motifs. Further O-H⋯O inter-actions involving the ethanol solvent mol-ecule connect the chains into a three-dimensional network. In addition, C-I⋯π inter-actions are observed. The inter-molecular inter-actions in the crystal structure were qu-anti-fied and analysed using Hirshfeld surface analysis.

Crystal structure and Hirshfeld surface analysis of 4-cyano-N-[(4-cyano-phen-yl)sulfon-yl]-N-[2-(5-methyl-furan-2-yl)phen-yl]benzene-sulfonamide.

In the title compound, C25H17N3O5S2, intra-molecular π-π inter-actions [centroid-to-centroid distance = 3.5640 (9) Å] are observed between the furan and benzene rings of the 4-cyano-phenyl group. In the crystal, mol-ecules are connected via C-H⋯O and C-H⋯N hydrogen bonds, forming layers parallel to the (100) plane. These layers are inter-connected by C-H⋯π inter-actions and weak van der Waals inter-actions. Hirshfeld surface analysis indicates that H⋯H (30.2%), N⋯H/H⋯N (22.3%), C⋯H/H⋯C (17.9%) and O⋯H/H⋯O (15.4%) inter-actions make the most significant contributions to the crystal packing.

Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4-fluoro-phen-yl)-2-formyl-7-methyl-imidazo[1,2-a]pyridin-1-ium chloride monohydrate.

In the title salt, C15H12FN2O+·Cl-·H2O, the imidazo[1,2-a]pyridin-1-ium ring system of the cation is almostly planar [maximum deviaition = -0.047 (2) Šfor the ring C atom with the attached arene ring] and forms a dihedral angle of 61.81 (6)° with the plane of the fluoro-phenyl ring. In the crystal, water mol-ecules form an R 2 4(8) motif parallel to the (100) plane by bonding with the chloride ions via O-H⋯Cl hydrogen bonds. The cations are connected along the b axis via N-H⋯O hydrogen bonds involving the O atoms of water mol-ecules, and C-H⋯O, C-H⋯Cl and π-π inter-actions [centroid-to-centroid distance = 3.6195 (8) Å] form layers parallel to the (100) plane. Furthermore, these layers are connected via π-π inter-actions [centroid-to-centroid distance = 3.8051 (9) Å] that further consolidate the crystal structure.

Crystal structure and Hirshfeld surface analysis of N-{[5-(4-methyl-phen-yl)-1,2-oxazol-3-yl]meth-yl}-1-phenyl-N-(prop-2-en-1-yl)methane-sulfonamide.

In the title compound, C21H22N2O3S, the 1,2-oxazole ring makes the dihedral angles of 9.16 (16) and 87.91 (17)°, respectively, with the toluene and phenyl rings, while they form a dihedral angle of 84.42 (15)° with each other. The C-S-N-Cpr and C-S-N-Cme (pr = propene, me = 3-methyl-1,2-oxazole) torsion angles are 86.8 (2) and -100.6 (3) °, respectively. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, generating a three-dimensional network. A Hirshfeld surface analysis was performed to investigate the contributions of the different inter-molecular contacts within the supra-molecular structure. The major inter-actions are H⋯H (53.6%), C⋯H/H⋯C (20.8%) and O⋯H/H⋯O (17.7%).

Crystal structure and Hirshfeld surface analysis of 5-(5-phenyl-1,2-oxazol-3-yl)-1,3,4-thia-diazol-2-amine.

The title compound, C11H8N4OS, crystallizes with two independent mol-ecules in the asymmetric unit. In the crystal, the N-H⋯N and C-H⋯N hydrogen bonds connect the mol-ecules, generating double layers parallel to the (001) plane. The layers are joined by C-H⋯π inter-actions to form a three-dimensional supra-molecular structure.

Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-bromo-1-(2-nitro-phen-yl)ethen-yl]-2-(4-fluoro-phen-yl)diazene.

In the title compound, C14H8Br2FN3O2, the nitro-substituted benzene ring and the 4-fluoro-phenyl ring form a dihedral angle of 65.73 (7)°. In the crystal, mol-ecules are linked into chains by C-H⋯O hydrogen bonds running parallel to the c-axis direction. The crystal packing is consolidated by C-F⋯π inter-actions and π-π stacking inter-actions, and short Br⋯O [2.9828 (13) Å] contacts are observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (17.4%), O⋯H/H⋯O (16.3%), Br⋯H/H⋯Br (15.5%), Br⋯C/C⋯Br (10.1%) and F⋯H/H⋯F (8.1%) contacts.

Crystal structure and Hirshfeld surface analysis of 5-acetyl-3-amino-6-methyl-N-phenyl-4-[(E)-2-phenyl-ethen-yl]thieno[2,3-b]pyridine-2-carbox-amide.

The asymmetric unit of the title compound, C25H21N3O2S, comprises four mol-ecules. Their conformations differ primarily in the orientations of the styryl and the N-phenyl-carboxamido groups. In the crystal, inter-molecular N-H⋯N, C-H⋯O and C-H⋯S hydrogen-bonding contacts as well a C-H⋯π(ring) inter-actions lead to the formation of a layer structure parallel to (010). Hirshfeld surface analysis revealed that H⋯H inter-actions represent the main contributions to the crystal packing.

Crystal structure and Hirshfeld surface analysis of ethyl (4R,4aS)-2-methyl-5,8-dioxo-6-phenyl-4a,5,6,7,7a,8-hexa-hydro-4H-furo[2,3-f]iso-indole-4-carboxyl-ate.

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) Å, θ = 49.11 (19)° and φ = 167.3 (2)°. The conformation of the fused pyrrolidine ring is that of an envelope. Mol-ecules are connected by inter-molecular C-H⋯O hydrogen bonds, C-H⋯π inter-actions and π-π stacking inter-actions [centroid-to-centroid distance = 3.9536 (11) Å, with a slippage of 2.047 Å], forming a three-dimensional network. The most important contributions to the surface contacts are from H⋯H (46.3%), O⋯H/H⋯O (31.5%) and C⋯H/H⋯C (17.3%) inter-actions, as concluded from a Hirshfeld surface analysis.

Crystal structure and Hirshfeld surface analysis of 4,5-di-bromo-6-methyl-2-phenyl-2,3,3a,4,5,6,7,7a-octa-hydro-3a,6-ep-oxy-1H-isoindol-1-one.

In the title compound, C15H15Br2NO2, two bridged tetra-hydro-furan 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 mol-ecules 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 inter-actions. One of the Br atoms is disordered over two sites with occupation ratio of 0.833 (8):0.167 (8).

Crystal structure and Hirshfeld surface analysis of 2-benzyl-4,5-di-bromo-2,3,3a,4,5,6,7,7a-octa-hydro-3a,6-ep-oxy-1H-isoindol-1-one.

The title compound, C15H15Br2NO2, crystallizes with two mol-ecules in the asymmetric unit of the unit cell. In both mol-ecules, the tetra-hydro-furan rings adopt an envelope conformation with the O atom as the flap and the pyrrolidine rings adopt an envelope conformation. In the crystal, mol-ecules 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 inter-actions. 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%) inter-actions, as concluded from a Hirshfeld surface analysis.

Crystal structure and Hirshfeld surface analysis of (RS)-3-hy-droxy-2-{[(3aRS,6RS,7aRS)-2-(4-methyl-phenyl-sulfon-yl)-2,3,3a,6,7,7a-hexa-hydro-3a,6-ep-oxy-1H-isoindol-6-yl]meth-yl}isoindolin-1-one.

The title compound, C24H24N2O5S, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In the central ring systems of both mol-ecules, the tetra-hydro-furan rings adopt envelope conformations, the pyrrolidine rings adopt a twisted-envelope conformation and the six-membered ring is in a boat conformation. In mol-ecules 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 inter-molecular O-H⋯O hydrogen bonds and weak inter-molecular C-H⋯O contacts link the mol-ecules, forming a three-dimensional network. In addition weak π-π stacking inter-actions [centroid-to centroid distance = 3.7124 (13) Å] between the pyrrolidine rings of the nine-membered groups of A mol-ecules are observed. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to qu-antify the inter-molecular inter-actions present in the crystal, indicating that the environments of the two mol-ecules are very similar. The most important contributions for the crystal packing are from H⋯H (55.8% for mol-ecule A and 53.5% for mol-ecule B), O⋯H/H⋯O (24.5% for mol-ecule A and 26.3% for mol-ecule B) and C⋯H/H⋯C (12.6% for mol-ecule A and 15.7% for mol-ecule B) inter-actions.

(3aS,4R,5R,6S,7aR)-4,5-Di-bromo-2-[4-(tri-fluoro-meth-yl)phen-yl]-2,3,3a,4,5,6,7,7a-octa-hydro-3a,6-ep-oxy-1H-isoindol-1-one: crystal structure and Hirshfeld surface analysis.

The asymmetric unit of the title compound, C15H12Br2F3NO2, consists of two crystallographically independent mol-ecules. In both mol-ecules, the pyrrolidine and tetra-hydro-furan rings adopt an envelope conformation. In the crystal, mol-ecule pairs generate centrosymmetric rings with R 2 2(8) motifs linked by C-H⋯O hydrogen bonds. These pairs of mol-ecules form a tetra-meric supra-molecular motif, leading to mol-ecular layers parallel to the (100) plane by C-H⋯π and C-Br⋯π inter-actions. Inter-layer van der Waals and inter-halogen inter-actions stabilize mol-ecular packing. The F atoms of the CF3 groups of both mol-ecules are disordered over two sets of sites with refined site occupancies of 0.60 (3)/0.40 (3) and 0.640 (15)/0.360 (15). The most important contributions to the surface contacts of both mol-ecules are from H⋯H (23.8 and 22.4%), Br⋯H/H⋯Br (18.3 and 12.3%), O⋯H/H⋯O (14.3 and 9.7%) and F⋯H/H⋯F (10.4 and 19.1%) inter-actions, as concluded from a Hirshfeld surface analysis.