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Synthesis, crystallographic analysis and Hirshfeld surface analysis of 4-bromo-2-{[2-(5-bromo-2-nitro-phen-yl)hydrazin-1-yl-idene]meth-yl}-5-fluoro-phenol.

ABSTRACT: The title compound, C₁₃H₈Br₂FN₃O₃, is nearly planar with a dihedral angle of 10.6 (4)° between the two benzene rings. Intra-molecular N-H⋯O and O-H⋯N hydrogen bonds occur. In the crystal, the mol-ecules are linked by weak C-H⋯O and C-H⋯Br hydrogen bonds. The roles of the inter-molecular inter-actions in the crystal packing were clarified using Hirshfeld surface analysis.

SUBMITTER: Yaman M

PROVIDER: S-EPMC6218898 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Synthesis, crystallographic analysis and Hirshfeld surface analysis of 4-bromo-2-{[2-(5-bromo-2-nitro-phen-yl)hydrazin-1-yl-idene]meth-yl}-5-fluoro-phenol.

Yaman Mavise M Aydemir Ercan E Dege Necmi N Agar Erbil E Iskenderov Turganbay S TS

Acta crystallographica. Section E, Crystallographic communications 20181019 Pt 11

The title compound, C13H8Br2FN3O3, is nearly planar with a dihedral angle of 10.6 (4)° between the two benzene rings. Intra-molecular N-H⋯O and O-H⋯N hydrogen bonds occur. In the crystal, the mol-ecules are linked by weak C-H⋯O and C-H⋯Br hydrogen bonds. The roles of the inter-molecular inter-actions in the crystal packing were clarified using Hirshfeld surface analysis. ...[more]

PMID: 30443395

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(Dimethyl sulfoxide-?O)[2-({(ethyl-sulfan-yl)[2-(2-oxidobenzyl-idene-?O)hydrazin-yl-idene-?N]meth-yl}-imino-meth-yl)-phenol-ato-?O]dioxidouranium(VI).

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4-Bromo-2-[(E)-(2-fluoro-5-nitro-phenyl)iminometh-yl]phenol.

Project description:The mol-ecular conformation of the title compound, C13H8BrFN2O3, is essentially planar, with maximum deviations of 0.076?(1) and -0.080?(2)?Å for the O atoms of the NO2 group. The mol-ecular conformation is stabilized by an intra-molecular O-H?N hydrogen bond, forming an S(6) ring motif. In the crystal, pairs of mol-ecules are linked via two pairs of C-H?O hydrogen bonds, forming inversion dimers that enclose R(2)2(7)R(2)2(10)R(2)2(7) ring motifs.

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Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-di-chloro-benzyl-idene]hydrazin-1-yl-idene}meth-yl)-6-meth-oxy-phenol and 4-bromo-2-({(E)-2-[(E)-2,6-di-chloro-benzyl-idene]hydrazin-1-yl-idene}meth-yl)phenol.

Project description:Each of the title dis-symmetric di-Schiff base compounds, C15H12Cl2N2O2 (I) and C14H9BrCl2N2O (II), features a central azo-N-N bond connecting two imine groups, each with an E-configuration. One imine bond in each mol-ecule connects to a 2,6-di-chloro-benzene substituent while the other links a 2-hydroxyl-3-meth-oxy-substituted benzene ring in (I) or a 2-hydroxyl-4-bromo benzene ring in (II). Each mol-ecule features an intra-molecular hydroxyl-O-H⋯N(imine) hydrogen bond. The C-N-N-C torsion angles of -151.0 (3)° for (I) and 177.8 (6)° (II) indicates a significant twist in the former. The common feature of the mol-ecular packing is the formation of supra-molecular chains. In (I), the linear chains are aligned along the a-axis direction and the mol-ecules are linked by meth-oxy-C-H⋯O(meth-oxy) and chloro-benzene-C-Cl⋯π(chlorobenzene) inter-actions. The chain in (II) is also aligned along the a axis but, has a zigzag topology and is sustained by Br⋯O [3.132 (4) Å] secondary bonding inter-actions. In each crystal, the chains pack without directional inter-actions between them. The non-covalent inter-actions are delineated in the study of the calculated Hirshfeld surfaces. Dispersion forces make the most significant contributions to the identified inter-molecular inter-actions in each of (I) and (II).

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