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Crystal structures of 4-meth-oxy-N-(4-methyl-phenyl)benzene-sulfonamide and N-(4-fluoro-phenyl)-4-meth-oxy-benzene-sulfonamide.

Rodrigues VZ, Preema CP, Naveen S, Lokanath NK, Suchetan PA - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: In (I), the benzene-sulfonamide ring is disordered over two orientations, in a 0.516 (7):0.484 (7) ratio, which are inclined to each other at 28.0 (1)°.In (I), the major component of the sulfonyl benzene ring and the aniline ring form a dihedral angle of 63.36 (19)°, while in (II), the planes of the two benzene rings form a dihedral angle of 44.26 (13)°.Further, a pair of C-H⋯O inter-molecular inter-actions consolidate the crystal packing of (II) into a three-dimensional supra-molecular architecture.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of PG Studies and Research in Chemistry, St Aloysius College, Mangalore, India.

ABSTRACT
Crystal structures of two N-(ar-yl)aryl-sulfonamides, namely, 4-meth-oxy-N-(4-methyl-phen-yl)benzene-sulfonamide, C14H15NO3S, (I), and N-(4-fluoro-phen-yl)-4-meth-oxy-benzene-sulfonamide, C13H12FNO3S, (II), were determined and analyzed. In (I), the benzene-sulfonamide ring is disordered over two orientations, in a 0.516 (7):0.484 (7) ratio, which are inclined to each other at 28.0 (1)°. In (I), the major component of the sulfonyl benzene ring and the aniline ring form a dihedral angle of 63.36 (19)°, while in (II), the planes of the two benzene rings form a dihedral angle of 44.26 (13)°. In the crystal structure of (I), N-H⋯O hydrogen bonds form infinite C(4) chains extended in [010], and inter-molecular C-H⋯πar-yl inter-actions link these chains into layers parallel to the ab plane. The crystal structure of (II) features N-H⋯O hydrogen bonds forming infinite one dimensional C(4) chains along [001]. Further, a pair of C-H⋯O inter-molecular inter-actions consolidate the crystal packing of (II) into a three-dimensional supra-molecular architecture.

No MeSH data available.


A view of (I), showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered benzene ring is shown.
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fig1: A view of (I), showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered benzene ring is shown.

Mentions: In (I) (Fig. 1 ▸), the benzene­sulfonamide ring is disordered due to rotation across the Car—S(O2) bond over two orientations, with atoms C2, C3, C5 and C6 occupying two positions with a 0.516 (7):0.484 (7) ratio. The dihedral angle between the two parts of disordered benzene ring, i.e. C1/C2A/C3A/C4/C5A/C6A and C1/C2B/C3B/C4/C5B/C6B, is 28.0 (1)°. The dihedral angle between the sulfonyl benzene ring (considering the major component) and the aniline ring is 63.36 (19)°, and the N—C bond in the C—SO2—NH—C segment has a gauche torsion with respect to the S=O bonds. Further, the mol­ecule is twisted at the S—N bond, with a C1—S1—N1—C7 torsion angle of 66.33 (19)°. The meth­oxy group in the sulfonyl­benzene ring is in the same plane as that of the major component of the disordered sulfonyl­benzene ring, the torsion angle C5A—C4—O3—C14 being −176.2 (4)°, while it deviates slightly from planarity with respect to the minor component, the C5B—C4—O3—C14 torsion angle being 165.9 (4)°.


Crystal structures of 4-meth-oxy-N-(4-methyl-phenyl)benzene-sulfonamide and N-(4-fluoro-phenyl)-4-meth-oxy-benzene-sulfonamide.

Rodrigues VZ, Preema CP, Naveen S, Lokanath NK, Suchetan PA - Acta Crystallogr E Crystallogr Commun (2015)

A view of (I), showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered benzene ring is shown.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645005&req=5

fig1: A view of (I), showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered benzene ring is shown.
Mentions: In (I) (Fig. 1 ▸), the benzene­sulfonamide ring is disordered due to rotation across the Car—S(O2) bond over two orientations, with atoms C2, C3, C5 and C6 occupying two positions with a 0.516 (7):0.484 (7) ratio. The dihedral angle between the two parts of disordered benzene ring, i.e. C1/C2A/C3A/C4/C5A/C6A and C1/C2B/C3B/C4/C5B/C6B, is 28.0 (1)°. The dihedral angle between the sulfonyl benzene ring (considering the major component) and the aniline ring is 63.36 (19)°, and the N—C bond in the C—SO2—NH—C segment has a gauche torsion with respect to the S=O bonds. Further, the mol­ecule is twisted at the S—N bond, with a C1—S1—N1—C7 torsion angle of 66.33 (19)°. The meth­oxy group in the sulfonyl­benzene ring is in the same plane as that of the major component of the disordered sulfonyl­benzene ring, the torsion angle C5A—C4—O3—C14 being −176.2 (4)°, while it deviates slightly from planarity with respect to the minor component, the C5B—C4—O3—C14 torsion angle being 165.9 (4)°.

Bottom Line: In (I), the benzene-sulfonamide ring is disordered over two orientations, in a 0.516 (7):0.484 (7) ratio, which are inclined to each other at 28.0 (1)°.In (I), the major component of the sulfonyl benzene ring and the aniline ring form a dihedral angle of 63.36 (19)°, while in (II), the planes of the two benzene rings form a dihedral angle of 44.26 (13)°.Further, a pair of C-H⋯O inter-molecular inter-actions consolidate the crystal packing of (II) into a three-dimensional supra-molecular architecture.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of PG Studies and Research in Chemistry, St Aloysius College, Mangalore, India.

ABSTRACT
Crystal structures of two N-(ar-yl)aryl-sulfonamides, namely, 4-meth-oxy-N-(4-methyl-phen-yl)benzene-sulfonamide, C14H15NO3S, (I), and N-(4-fluoro-phen-yl)-4-meth-oxy-benzene-sulfonamide, C13H12FNO3S, (II), were determined and analyzed. In (I), the benzene-sulfonamide ring is disordered over two orientations, in a 0.516 (7):0.484 (7) ratio, which are inclined to each other at 28.0 (1)°. In (I), the major component of the sulfonyl benzene ring and the aniline ring form a dihedral angle of 63.36 (19)°, while in (II), the planes of the two benzene rings form a dihedral angle of 44.26 (13)°. In the crystal structure of (I), N-H⋯O hydrogen bonds form infinite C(4) chains extended in [010], and inter-molecular C-H⋯πar-yl inter-actions link these chains into layers parallel to the ab plane. The crystal structure of (II) features N-H⋯O hydrogen bonds forming infinite one dimensional C(4) chains along [001]. Further, a pair of C-H⋯O inter-molecular inter-actions consolidate the crystal packing of (II) into a three-dimensional supra-molecular architecture.

No MeSH data available.