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5-Bromo­salicylaldehyde benzoyl­hydrazone

✍ Scribed by Liu, Hui-Yan ;Wang, Hai-Ying ;Gao, Feng ;Lu, Zai-Sheng ;Niu, De-Zhong

Publisher
International Union of Crystallography
Year
2006
Tongue
English
Weight
177 KB
Volume
62
Category
Article
ISSN
1600-5368

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Molecules of 5-chlorosalicylaldehyde benzoylhydrazone, C 14 H 11 ClN 2 O 2 , are linked by an intermolecular aminocarbonyl hydrogen bond into a linear chain that runs along the a axis of the orthorhombic unit cell.

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Nearly planar molecules of the title compound, C 11 H 11 N 3 O 4 , are linked by O-HÁ Á ÁO hydrogen bonds to form zigzag chains along the c axis; adjacent chains are, in turn, linked by weaker N-HÁ Á ÁO hydrogen bonds to form layers perpendicular to the a axis of the orthorhombic unit cell.

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Molecules of 5-bromo-1H-indole-3-carbaldehyde 3-methoxybenzoylylhydrazone, C 17 H 14 BrN 3 O 2 , are paired by aminocarbonyl hydrogen bonds over a center of inversion, and adjacent pairs are further linked by hydrogen bonds into ribbons.

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The molecule of the title compound, C~14~H~11~N~3~O~5~, is approximately planar, the dihedral angles between the two aromatic rings being 4.63 (7)°. O—H...N, N—H...O and O—H...O hydrogen bonds and π–π stacking interactions help to consolidate the crystal packing.

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An i.r. study of Fe complexes prepared from salicylaldehyde benzoyl hydrazone and seven similar chelating agents allowed the assignment of some iron-ligand bands. The amide I and ~b--O band shifts indicate that the ligand O atoms are directly linked to Fe. The analogy between FdI and Fe In complexes

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A view of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids for non-H atoms. The intramolecular hydrogen bond is shown as a dashed line.