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4-[(5-Bromo-2-hydroxy-benzyl-idene)amino]-N-(4,6-dimethyl-pyrimidin-2-yl)benzene-sulfonamide-4-bromo-2-[(E)-({4-[(4,6-dimethyl-pyrimidin-2-yl)sulfamo-yl]phen-yl}iminio)meth-yl]phenolate [0.61 (7)/0.39 (7)].

Shad HA, Tahir MN, Chohan ZH - Acta Crystallogr Sect E Struct Rep Online (2008)

Bottom Line: The geometry of the title mol-ecule points to the enol (OH-C=C-C=N) form as the major tautomer, however two electron-density maxima corresponding to the H atoms of the OH and NH groups, found in the region of a strong intra-molecular N⋯H⋯O hydrogen bond, do not allow the elimination of the presence of the zwitterionic (O(-)-C=C-C=NH(+)) form in the crystal.An inter-molecular N-H⋯O hydrogen bond links mol-ecules into chains extended along the a axis and a C-H⋯O link is also present.The H atoms of one of the methyl groups are disordered over two sites with an occupancy ratio of 0.72 (7):0.28 (7).

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ABSTRACT
The title compound, 0.61C(19)H(17)BrN(4)O(3)S·0.39C(19)H(17)BrN(4)O(3)S, is a Schiff base derived from 5-bromo-salicylaldehyde and 4-amino-N-(4,6-dimethyl-2-pyrimidin-yl)benzene-sulfonamide(sulfamethazine) and is isostructural with its chloro analogue. The geometry of the title mol-ecule points to the enol (OH-C=C-C=N) form as the major tautomer, however two electron-density maxima corresponding to the H atoms of the OH and NH groups, found in the region of a strong intra-molecular N⋯H⋯O hydrogen bond, do not allow the elimination of the presence of the zwitterionic (O(-)-C=C-C=NH(+)) form in the crystal. Refinement of the occupancies of these H atoms gave a 0.61 (7):0.39 (7) ratio of the enolic and zwitterionic forms. The two benzene rings within the mol-ecule are nearly coplanar and the central benzene ring forms a dihedral angle of 84.1 (1)° with the pyrimidine fragment. An inter-molecular N-H⋯O hydrogen bond links mol-ecules into chains extended along the a axis and a C-H⋯O link is also present. The H atoms of one of the methyl groups are disordered over two sites with an occupancy ratio of 0.72 (7):0.28 (7).

No MeSH data available.


Crystal packing of the title compound.
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Fap2: Crystal packing of the title compound.


4-[(5-Bromo-2-hydroxy-benzyl-idene)amino]-N-(4,6-dimethyl-pyrimidin-2-yl)benzene-sulfonamide-4-bromo-2-[(E)-({4-[(4,6-dimethyl-pyrimidin-2-yl)sulfamo-yl]phen-yl}iminio)meth-yl]phenolate [0.61 (7)/0.39 (7)].

Shad HA, Tahir MN, Chohan ZH - Acta Crystallogr Sect E Struct Rep Online (2008)

Crystal packing of the title compound.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2968005&req=5

Fap2: Crystal packing of the title compound.
Bottom Line: The geometry of the title mol-ecule points to the enol (OH-C=C-C=N) form as the major tautomer, however two electron-density maxima corresponding to the H atoms of the OH and NH groups, found in the region of a strong intra-molecular N⋯H⋯O hydrogen bond, do not allow the elimination of the presence of the zwitterionic (O(-)-C=C-C=NH(+)) form in the crystal.An inter-molecular N-H⋯O hydrogen bond links mol-ecules into chains extended along the a axis and a C-H⋯O link is also present.The H atoms of one of the methyl groups are disordered over two sites with an occupancy ratio of 0.72 (7):0.28 (7).

View Article: PubMed Central - HTML - PubMed

ABSTRACT
The title compound, 0.61C(19)H(17)BrN(4)O(3)S·0.39C(19)H(17)BrN(4)O(3)S, is a Schiff base derived from 5-bromo-salicylaldehyde and 4-amino-N-(4,6-dimethyl-2-pyrimidin-yl)benzene-sulfonamide(sulfamethazine) and is isostructural with its chloro analogue. The geometry of the title mol-ecule points to the enol (OH-C=C-C=N) form as the major tautomer, however two electron-density maxima corresponding to the H atoms of the OH and NH groups, found in the region of a strong intra-molecular N⋯H⋯O hydrogen bond, do not allow the elimination of the presence of the zwitterionic (O(-)-C=C-C=NH(+)) form in the crystal. Refinement of the occupancies of these H atoms gave a 0.61 (7):0.39 (7) ratio of the enolic and zwitterionic forms. The two benzene rings within the mol-ecule are nearly coplanar and the central benzene ring forms a dihedral angle of 84.1 (1)° with the pyrimidine fragment. An inter-molecular N-H⋯O hydrogen bond links mol-ecules into chains extended along the a axis and a C-H⋯O link is also present. The H atoms of one of the methyl groups are disordered over two sites with an occupancy ratio of 0.72 (7):0.28 (7).

No MeSH data available.