Crystal structure and Hirshfeld surface analysis of methyl 4-[(E)-2-(5-bromo-2-meth-oxy-benzyl-idene)hydrazin-yl]-3-nitro-benzoate.
ABSTRACT: The title compound, C16H14BrN3O5, is a novel halogen (Br) substituted hydrazine derivative. The hydrazine derivatives were the group of compounds with the general structure, R1R2C=NNH2 (Uppal et al., 2011 ?), with the central RC=NNH2 moiety bridging two different groups on both sides. An all-trans configuration of the backbone (RC=NNH2) results in an extended mol-ecular conformation. The dihedral angle between the 5-bromo-2-meth-oxy-phenyl ring and the nitrophenyl ring is 4.4?(3)°. Intra-molecular N-H?O inter-actions form S(6) graph-set motifs, while C-H?O and C-H?N inter-actions form S(5) graph-set motifs. Symmetry-related mol-ecules are linked by C-H?O inter-molecular inter-actions forming an R21(10) graph-set motif. There are nearly face-to-face directional specific ?-? stacking inter-actions between the centroids of the nitrophenyl ring and the benzene ring of the 5-bromo-2-meth-oxy group [centroid-centroid distance = 3.6121?(5)?Å and slippage = 1.115?Å], which also contributes to the mol-ecular packing. The Hirshfeld surface analysis was performed in order to visualize, explore and qu-antify the inter-molecular inter-actions in the crystal lattice of the title compound.
Project description:The reaction between 5-nitro-isatin and phenyl-hydrazine in acidic ethanol yields the title compound, C14H10N4O3, whose mol-ecular structure deviates slightly from a planar geometry (r.m.s. deviation = 0.065?Å for the mean plane through all non-H atoms). An intra-molecular N-H?O hydrogen bond is present, forming a ring of graph-set motif S(6). In the crystal, mol-ecules are linked by N-H?O and C-H?O hydrogen-bonding inter-actions into a two-dimensional network along (120), and rings of graph-set motif R22(8), R22(26) and R44(32) are observed. Additionally, a Hirshfeld surface analysis suggests that the mol-ecules are stacked along  through C=O?Cg inter-actions and indicates that the most important contributions for the crystal structure are O?H (28.5%) and H?H (26.7%) inter-actions. An in silico evaluation of the title compound with the DHFR enzyme (di-hydro-folate reductase) was performed. The isatin-hydrazone derivative and the active site of the selected enzyme show N-H?O(ASP29), N-H?O(ILE96) and Cg?Cg(PHE33) inter-actions.
Project description:The title mol-ecular salts, C16H16NO+·PF6 -, (I), and C21H21N2 +·PF6 -, (II), are pyridine derivatives. In compound (I), the cation comprises a methyl N-substituted pyridine ring and a meth-oxy-substituted benzene ring connected by a C=C double bond. The F atoms of the PF6 - anion are disordered over two sets of sites with refined occupancy factors of 0.614 (7):0.386 (7). In compound (II), the cation comprises a pyridine ring attached to unsubstituted phenyl ring and a di-methyl-aniline ring, which are connected by a C=C double bond. The anion is PF6 -. In both salts, the cation adopts an E configuration with respect to the C=C bond. The pyridine ring makes a dihedral angle of 9.86 (12)° with the meth-oxy-substituted benzene ring in compound (I) and 11.2 (3)° with the di-methyl-amine-substituted benzene ring in compound (II). In compound (I), the crystal packing is stabilized by weak C-H⋯F inter-molecular inter-actions which result in R 4 3(14) ring motifs, forming mol-ecular sheets running parallel to (03). These are further stabilized by weak P-F⋯π interactions. In compound (II), the crystal packing is stabilized by C-H⋯F inter-actions, which result in R 6 6(40) ring motifs, forming mol-ecular sheets running parallel to (101) and these are further connected by π-π inter-actions.
Project description:The crystal structure of the title compound, C(16)H(11)F(3)N(4)O(2)S, is stabilized in the form of polymeric chains by N-H?O inter-actions. In the mol-ecular structure, two S(5) ring motifs are formed by intra-molecular N-H?N and N-H?O hydrogen bonding and two S(6) rings are present due to N-H?O and C-H?S inter-actions. ?-? inter-actions are present with distances of 3.2735?(17), 3.563?(2) and 3.664?(4)/3.688?(3)?Å between the centroids of the heterocyclic rings, between the centroids of the heterocyclic ring and trifluoro-meth-oxy-substituted phenyl ring, and between the centroids of the trifluoro-meth-oxy-substituted phenyl rings, respectively. The trifluoro-meth-oxy-phenyl group is disordered over two sites with an occupancy ratio of 0.642?(10):0.358?(10).
Project description:The title compound, C(23)H(30)N(2)O(4), is a Mannich base useful for studying the effect of an electron-donating phenol substituent on intra-molecular hydrogen bonding. In the mol-ecular structure, the cyclo-hexane ring adopts a chair conformation and the five-membered ring has a twisted envelope conformation. Each meth-oxy group is oriented in the same plane of the respective aromatic ring, showing torsion angles below 11.8?(3)° and bond angles between the meth-oxy group and the aromatic ring of 116.6?(2) and 116.6?(1)°. The structure shows inter-actions between two the N atoms of the heterocyclic ring and the hy-droxy groups by intra-molecular O-H?N hydrogen-bonding inter-actions. In the crystal, C-H?O inter-actions are observed. The crystal studied was a racemic mixture of RR and SS enanti-omers.
Project description:In the title compound, C10H14Br4O5, synthesized from the meth-oxy Schiff base N-(pyridin-2-ylmeth-yl)meth-oxy-aniline and mol-ecular bromine, the cyclo-hexa-none ring has a chair conformation with one of the four meth-oxy groups equatorially orientated with respect to the carbonyl group and the others axially orientated. The C-Br bond lengthsvary from 1.942?(4) to1.964?(4)?Å. In the crystal, weak C-H?Ocarbon-yl hydrogen-bonding inter-actions generate chains extending along the b-axis direction. Also present in the structure are two short inter-molecular Br?Ometh-oxy inter-actions [3.020?(3) and 3.073?(4)?Å].
Project description:In the title compound, C12H11Cl3N2O4, the dihedral angle between the aromatic ring and the hydrazine (NH-N=C) grouping is 52.2?(3)°. The butanedioate groups exhibit planar conformations. An intra-molecular N-H?O hydrogen bond links the N-H group of the hydrazine to one of the meth-oxy groups of the butane-dioate moiety. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds and ?-? inter-actions are also observed [centroid-centroid separation = 3.535?(1)?Å].
Project description:The title compound, C23H30N2O4, a di-Mannich base derived from 4-meth-oxy-phenol and cis-1,2-di-amine-cyclo-hexane, has a perhydro-benzimidazolidine nucleus, in which the cyclo-hexane ring adopts a chair conformation and the heterocyclic ring has a half-chair conformation with a C-N-C-C torsion angles of -48.14?(15) and -14.57?(16)°. The mean plane of the heterocycle makes dihedral angles of 86.29?(6) and 78.92?(6)° with the pendant benzene rings. The mol-ecular structure of the title compound shows the presence of two inter-actions between the N atoms of the imidazolidine ring and the hydroxyl groups through intra-molecular O-H?N hydrogen bonds with graph-set motif S(6). The unobserved lone pairs of the N atoms are presumed to be disposed in a syn conformation, being only the second example of an exception to the typical 'rabbit-ears' effect in 1,2-di-amines.
Project description:The mol-ecular structure of the title compound, [Fe(C9H6BrS)(C13H7F6)], consists of a ferrocene backbone with a bis-(tri-fluoro-meth-yl)phenyl group at one cyclo-penta-dienyl ring and a thio-phene heterocycle at the other cyclo-penta-dienyl ring. The latter is disordered over two sets of sites in a 0.6:0.4 ratio. In the crystal structure, intra-molecular ?-? inter-actions between the thienyl and the phenyl substituent [centroid-centroid distance 3.695?(4)?Å] and additional weak T-shaped ?-? inter-actions between the thienyl and the phenyl-substituted cyclo-penta-dienyl ring [4.688?(6)?Å] consolidate the crystal packing.
Project description:In the title compound, C(24)H(28)N(2)O(4), the dioxalane ring has an envelope conformation. The cyclo-hexane ring adopts a chair conformation. The dihedral angle between the benzene rings is 72.5?(3)°. The mol-ecular conformation is stabilized by two intra-molecular O-H?N hydrogen-bonding inter-actions with an S(6) graph-set motif. The crystal structure is stabilized by van der Waals inter-actions.
Project description:In the title compound, C18H17FN2O, the imidazole ring makes dihedral angles of 68.81?(6) and 25.20?(8)° with the meth-oxy-phenyl and fluoro-phenyl rings, respectively. The dihedral angle between the meth-oxy-phenyl and fluoro-phenyl ring is 71.89?(6)°. In the crystal, mol-ecules are linked into inversion dimers with an R 2 (2)(8) graph-set motif by pairs of weak C-H?F inter-actions.