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4-(5-Chloro-2-hydroxy-benzyl-idene-amino)-N-(4,6-dimethyl-pyrimidin-2-yl)benzene-sulfonamide.

ABSTRACT: The title compound, C(19)H(17)ClN(4)O(3)S, is a Schiff base compound of 5-chloro-salicylaldehyde and sulfamethazine [4-amino-N-(4,6-dimethyl-2-pyrimidin-yl)benzene-sulfonamide]. The geometry around the S atom is distorted tetra-hedral, comprising two O atoms of the sulfonyl group, a C atom of a benzene ring and the amino N atom. The title compound has an intra-molecular O-H⋯N hydrogen bond and two inter-molecular C-H⋯O and N-H⋯O hydrogen bonds, which link neighbouring mol-ecules into 10-membered rings. As a result of an unavoidable conformational arrangement, a slightly short intra-molecular contact of distance 2.59 Å exists between an O atom of the sulfonyl group and an H atom of the sulfamethazine benzene ring.

SUBMITTER: Chohan ZH

PROVIDER: S-EPMC2960946 | biostudies-literature | 2008 Mar

REPOSITORIES: biostudies-literature

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4-(5-Chloro-2-hydroxy-benzyl-idene-amino)-N-(4,6-dimethyl-pyrimidin-2-yl)benzene-sulfonamide.

Chohan Zahid H ZH Tahir M Nawaz MN Shad Hazoor A HA Khan Islam Ullah IU

Acta crystallographica. Section E, Structure reports online 20080305 Pt 4

The title compound, C(19)H(17)ClN(4)O(3)S, is a Schiff base compound of 5-chloro-salicylaldehyde and sulfamethazine [4-amino-N-(4,6-dimethyl-2-pyrimidin-yl)benzene-sulfonamide]. The geometry around the S atom is distorted tetra-hedral, comprising two O atoms of the sulfonyl group, a C atom of a benzene ring and the amino N atom. The title compound has an intra-molecular O-H⋯N hydrogen bond and two inter-molecular C-H⋯O and N-H⋯O hydrogen bonds, which link neighbouring mol-ecules into 10-membered ...[more]

PMID: 21202046

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4-[(E)-(5-Chloro-2-hydroxy-benzyl-idene)amino]benzene-sulfonamide.

Project description:In the mol-ecule of title compound, C(13)H(11)ClN(2)O(3)S, the aromatic rings are oriented at a dihedral angle of 12.27 (3)°. An intra-molecular O-H⋯N hydrogen bond results in the formation of a planar (mean deviation 0.0083 Å) six-membered ring, which is nearly coplanar with the adjacent ring at a dihedral angle of 2.36 (13)°. In the sulfonamide group, the S atom is 0.457 (3) Å from the plane through the O and N atoms. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules.

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4-{2-[(5-Chloro-2-hydroxy-benzyl-idene)amino]eth-yl}benzene-sulfonamide.

Project description:In the mol-ecule of the title compound, C(15)H(15)ClN(2)O(3)S, the S atom adopts a distorted tetra-hedral coordination geometry with two O atoms, one N atom of the amide group and one C atom of the aromatic ring. An intra-molecular O-H⋯N hydrogen bond results in the formation of a planar six-membered ring, which is oriented with respect to the adjacent aromatic ring at a dihedral angle of 3.38 (11)°. Thus, the two rings are nearly coplanar. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

| S-EPMC2960939 | biostudies-literature

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)].

Project description: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).

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4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)benzene-sulfonamide-benzoic acid (1/1).

Project description:The constituents of the title co-crystal, C(12)H(14)N(4)O(2)S·C(7)H(6)O(2), are connected by an eight-membered hetero-synthon {⋯NCNH⋯OCOH}, whereby the carb-oxy-lic acid forms donor and acceptor hydrogen bonds with a pyrimidine N atom and the adjacent amine, respectively. The dimeric aggregates thus formed are arranged in rows with their terminal NH(2) groups forming N-H⋯O hydrogen bonds with neighbouring aggregates to form a two-dimensional array in the ac plane with an overall T-shaped topology. Layers inter-digitate along the b axis being connected by C-H⋯O, C-H⋯π and π-π [centroid-centroid distance = 3.6316 (19) Å] inter-actions.

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4-{2-[(5-Bromo-2-hydroxy-benzyl-idene)amino]eth-yl}benzene-sulfonamide.

Project description:In the title compound, C(15)H(15)BrN(2)O(3)S, the dihedral angle between the benzene rings is 6.1 (2)° and an intra-molecular O-H⋯N hydrogen bond helps to establish the conformation. In the crystal structure, the mol-ecules are linked by way of N-H⋯O and C-H⋯O hydrogen bonds.

| S-EPMC2970355 | biostudies-literature

4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)-benzene-sulfonamide-4-nitro-benzoic acid (1/1).

Project description:In the asymmetric unit of the title co-crystal, C(7)H(5)NO(4)·C(12)H(14)N(4)O(2)S, there are two independent but conformationally similar heterodimers, which are formed through inter-molecular N-H⋯O(carb-oxy) and carbox-yl-pyrimidine O-H⋯N hydrogen-bond pairs, giving a cyclic motif [graph set R(2) (2)(8)]. The dihedral angles between the rings in the sulfonamide molecules are 78.77 (8) and 82.33 (9)° while the dihedral angles between the ring and the CO(2)H group in the acids are 2.19 (9) and 7.02 (10)°. A two-dimensional structure parallel to the ab plane is generated from the heterodimer units through hydrogen-bonding associations between NH(2) and sulfone groups. Between neighbouring two-dimensional arrays there are two types of aromatic π-π stacking inter-actions involving either one of the pyrimidine rings and a 4-nitro-benzoic acid mol-ecule [minimum ring centroid separation = 3.5886 (9) Å] or two acid mol-ecules [minimum ring centroid separation = 3.7236 (10) Å].

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4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)benzene-sulfonamide-2-nitro-benzoic acid (1/1).

Project description:In the asymmetric unit of the title co-crystal, C(12)H(14)N(4)O(2)S·C(7)H(5)NO(4), the sulfamethazine and 2-nitro-benzoic acid mol-ecules form a heterodimer through inter-molecular amide-carb-oxy-lic acid N-H⋯O and carb-oxy-lic acid-pyrimidine O-H⋯N hydrogen-bond pairs, giving a cyclic motif [graph set R(2) (2)(8)]. The dihedral angle between the two aromatic ring systems in the sulfamethazine mol-ecule is 88.96 (18)° and the nitro group of the acid is 50% rotationally disordered. Secondary aniline N-H⋯O(sulfone) hydrogen-bonding associations give a two-dimensional structure lying parallel to the ab plane.

| S-EPMC3569767 | biostudies-literature

N-(4,6-Dimethyl-pyrimidin-2-yl)-4-(oxolan-2-ylamino)benzene-sulfonamide.

Project description:The title compound, C(16)H(20)N(4)O(3)S, adopts an l-shaped conformation, as seen by the dihedral angle of 76.93 (7)° formed between the two aromatic rings. The most notable feature of the crystal packing is the formation of N-H⋯O and N-H⋯N hydrogen bonds that lead to supra-molecular chains orientated along the b axis.

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N-(2,3-Dihydro-1,3-thia-zol-2-yl-idene)-4-[(2-hydroxy-benzyl-idene)amino]benzene-sulfonamide.

Project description:The title compound, C(16)H(13)N(3)O(3)S(2), was prepared by reaction of salicylaldehyde and sulfathia-zole in methanol. The dihedral angle between the central benzene ring and the thia-zole ring is 85.2 (2)° and that between the two benzene rings is 17.9 (2)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are held together by inter-molecular N-H⋯N and C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

| S-EPMC2969909 | biostudies-literature

4-{[4-(Di-methyl-amino)-benzyl-idene]amino}-benzene-sulfonamide.

Project description:The title Schiff base compound, C15H17N3O2S, is non-planar with a dihedral angle of 69.88 (4)° between the planes of the benzene rings. In the crystal, pairs of N-H⋯N hydrogen bonds, between the sulfonamide nitro-gen-H atom and the azomethine N atom, link the mol-ecules into inversion dimers, forming R 2 (2)(16) ring motifs. These dimers are linked by N-H⋯O hydrogen bonds, between the sulfonamide nitro-gen-H atom and one sulfonamide O atom, forming sheets lying parallel to (100). Within the sheets there are weak parallel slipped π-π inter-actions involving inversion-related benzene-sulfonamide rings [centroid-centroid distance = 3.8800 (9) Å; normal distance = 3.4796 (6) Å; slippage = 1.717 Å].

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