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Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[5-(4-methyl-benz-yl)-6-oxo-3-phenyl-1,6-di-hydro-pyridazin-1-yl]acetic acid.

ABSTRACT: The title pyridazinone derivative, C₂₀H₁₈N₂O₃, is not planar. The phenyl ring and the pyridazine ring are inclined to each other by 10.55 (12)°, whereas the 4-methyl-benzyl ring is nearly orthogonal to the pyridazine ring, with a dihedral angle of 72.97 (10)°. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers with an R ₂ ²(14) ring motif. The dimers are linked by C-H⋯O hydrogen bonds, generating ribbons propagating along the c-axis direction. The inter-molecular inter-actions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. They revealed that the most significant contributions to the crystal packing are from H⋯H (48.4%), H⋯O/O⋯H (21.8%) and H⋯C/C⋯H (20.4%) contacts. Mol-ecular orbital calculations providing electron-density plots of HOMO and LUMO mol-ecular orbitals and mol-ecular electrostatic potentials (MEP) were also computed, both with the DFT/B3LYP/6-311 G++(d,p) basis set.

SUBMITTER: Daoui S

PROVIDER: S-EPMC6895937 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chloro-benz-yl)-6-oxo-3-phenyl-1,6-di-hydro-pyridazin-1-yl]acetate.

Project description:The title pyridazinone derivative, C21H19ClN2O3, is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41?(13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19?(13)°]. In the crystal, C-H?O hydrogen bonds generate dimers with R 2 2(10) and R 2 2(24) ring motifs which are linked by C-H?O inter-actions, forming chains extending parallel to the c-axis direction. The inter-molecular inter-actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most significant contributions to the crystal packing are from H?H (44.5%), C?H/H?C (18.5%), H?O/H?O (15.6%), Cl?H/H?Cl (10.6%) and C?C (2.8%) contacts.

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Project description:Two polymorphs of the title compound, C19H16N2O3, were obtained from ethano-lic (polymorph I) and methano-lic solutions (polymorph II), respectively. Both polymorphs crystallize in the monoclinic system with four formula units per cell and a complete mol-ecule in the asymmetric unit. The main difference between the mol-ecules of (I) and (II) is the reversed position of the hy-droxy group of the carb-oxy-lic function. All other conformational features are found to be similar in the two mol-ecules. The different orientation of the OH group results in different hydrogen-bonding schemes in the crystal structures of (I) and (II). Whereas in (I) inter-molecular O-H?O hydrogen bonds with the pyridazinone carbonyl O atom as acceptor generate chains with a C(7) motif extending parallel to the b-axis direction, in the crystal of (II) pairs of inversion-related O-H?O hydrogen bonds with an R 2 2(8) ring motif between two carb-oxy-lic functions are found. The inter-molecular inter-actions in both crystal structures were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

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Crystal structure and Hirshfeld surface analysis of 4-(4-methyl-benz-yl)-6-phenyl-pyridazin-3(2H)-one.

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