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(E)-2-{(2-Hydroxy-naphthalen-1-yl)methyl-ene}hydrazinecarboxamide.

Hijji YM, Oladeinde O, Butcher RJ, Jasinski JP - Acta Crystallogr Sect E Struct Rep Online (2009)

Bottom Line: The crystal packing is influenced by N-H⋯O hydrogen bonding which includes a bifurcated hydrogen bond between the amide N atom and nearby carboxyl and hydroxyl O atoms.A second bifurcated hydrogen bond occurs between the hydroxyl O atom and nearby amide (inter-molecular) and hydrazine (intra-molecular) N atoms.As a result, mol-ecules are linked into a co-operative hydrogen-bonded network of infinite one-dimensional O-H⋯O-H⋯O-H chains along the (101) plane of the unit cell in a zigzag pattern, the dihedral angle between the mean planes of the naphthalene groups of adjacent mol-ecules in the chain being 86.9 (2)°.

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ABSTRACT
In the title mol-ecule, C(12)H(11)N(3)O(2), the dihedral angle between the mean planes of the naphthalene and carboxamide groups is 28.9 (8)°. The hydrazine N atoms are twisted slightly out of the plane of the carboxamide group [C-C-N-N torsion angle = -175.06 (13)°]. The crystal packing is influenced by N-H⋯O hydrogen bonding which includes a bifurcated hydrogen bond between the amide N atom and nearby carboxyl and hydroxyl O atoms. A second bifurcated hydrogen bond occurs between the hydroxyl O atom and nearby amide (inter-molecular) and hydrazine (intra-molecular) N atoms. As a result, mol-ecules are linked into a co-operative hydrogen-bonded network of infinite one-dimensional O-H⋯O-H⋯O-H chains along the (101) plane of the unit cell in a zigzag pattern, the dihedral angle between the mean planes of the naphthalene groups of adjacent mol-ecules in the chain being 86.9 (2)°. A MOPAC PM3 calculation provides support to these observations.

No MeSH data available.


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The molecular packing for C12H11N3O2 viewed down the b axis showing the cooperative hydrogen bond network of infinite one–dimensional O—H···O—H···O—H chains along the (1 0 1) plane of the unit cell in a zigzag pattern. Dashed lines indicate intermolecular N—H···O, and intramolecular O–H···N hydrogen bonds.
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Fap3: The molecular packing for C12H11N3O2 viewed down the b axis showing the cooperative hydrogen bond network of infinite one–dimensional O—H···O—H···O—H chains along the (1 0 1) plane of the unit cell in a zigzag pattern. Dashed lines indicate intermolecular N—H···O, and intramolecular O–H···N hydrogen bonds.


(E)-2-{(2-Hydroxy-naphthalen-1-yl)methyl-ene}hydrazinecarboxamide.

Hijji YM, Oladeinde O, Butcher RJ, Jasinski JP - Acta Crystallogr Sect E Struct Rep Online (2009)

The molecular packing for C12H11N3O2 viewed down the b axis showing the cooperative hydrogen bond network of infinite one–dimensional O—H···O—H···O—H chains along the (1 0 1) plane of the unit cell in a zigzag pattern. Dashed lines indicate intermolecular N—H···O, and intramolecular O–H···N hydrogen bonds.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2977788&req=5

Fap3: The molecular packing for C12H11N3O2 viewed down the b axis showing the cooperative hydrogen bond network of infinite one–dimensional O—H···O—H···O—H chains along the (1 0 1) plane of the unit cell in a zigzag pattern. Dashed lines indicate intermolecular N—H···O, and intramolecular O–H···N hydrogen bonds.
Bottom Line: The crystal packing is influenced by N-H⋯O hydrogen bonding which includes a bifurcated hydrogen bond between the amide N atom and nearby carboxyl and hydroxyl O atoms.A second bifurcated hydrogen bond occurs between the hydroxyl O atom and nearby amide (inter-molecular) and hydrazine (intra-molecular) N atoms.As a result, mol-ecules are linked into a co-operative hydrogen-bonded network of infinite one-dimensional O-H⋯O-H⋯O-H chains along the (101) plane of the unit cell in a zigzag pattern, the dihedral angle between the mean planes of the naphthalene groups of adjacent mol-ecules in the chain being 86.9 (2)°.

View Article: PubMed Central - HTML - PubMed

ABSTRACT
In the title mol-ecule, C(12)H(11)N(3)O(2), the dihedral angle between the mean planes of the naphthalene and carboxamide groups is 28.9 (8)°. The hydrazine N atoms are twisted slightly out of the plane of the carboxamide group [C-C-N-N torsion angle = -175.06 (13)°]. The crystal packing is influenced by N-H⋯O hydrogen bonding which includes a bifurcated hydrogen bond between the amide N atom and nearby carboxyl and hydroxyl O atoms. A second bifurcated hydrogen bond occurs between the hydroxyl O atom and nearby amide (inter-molecular) and hydrazine (intra-molecular) N atoms. As a result, mol-ecules are linked into a co-operative hydrogen-bonded network of infinite one-dimensional O-H⋯O-H⋯O-H chains along the (101) plane of the unit cell in a zigzag pattern, the dihedral angle between the mean planes of the naphthalene groups of adjacent mol-ecules in the chain being 86.9 (2)°. A MOPAC PM3 calculation provides support to these observations.

No MeSH data available.


Related in: MedlinePlus