The crystal structure of the title sulfonamide, C 10 H 15 NO 2 S, comprises two molecules in the asymmetric unit. The S=O bond lengths of the sulfonamide functional group range from 1.428 (2) to 1.441 (2) Å, with S—C bond lengths of 1.766 (3) Å (for both molecules in the asymmetric unit), and S—N bond lengths of 1.618 (2) and 1.622 (3) Å, respectively. When both molecules are viewed down the N—S bond, the propyl group is gauche to the toluene moiety. In the crystal structure, molecules of the title compound are arranged in an intricate three-dimensional network that is formed via intermolecular C—H...O and N—H...O hydrogen bonds. The crystal structure was refined from a crystal twinned by inversion.
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Crystal structure of N , N -diisopropyl-4-methylbenzenesulfonamide
The synthesis of the title compound, C 13 H 21 NO 2 S, is reported here along with its crystal structure. This compound crystallizes with two molecules in the asymmetric unit. The sulfonamide functional group of this structure features S=O bond lengths ranging from 1.433 (3) to 1.439 (3) Å, S—C bond lengths of 1.777 (3) and 1.773 (4) Å, and S—N bond lengths of 1.622 (3) and 1.624 (3) Å. When viewing the molecules down the S—N bond, the isopropyl groups are gauche to the aromatic ring. On each molecule, two methyl hydrogen atoms of one isopropyl group are engaged in intramolecular C—H...O hydrogen bonds with a nearby sulfonamide oxygen atom. Intermolecular C—H...O hydrogen bonds and C—H...π interactions link molecules of the title compound in the solid state.
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- NSF-PAR ID:
- 10162643
- Date Published:
- Journal Name:
- Acta Crystallographica Section E Crystallographic Communications
- Volume:
- 76
- Issue:
- 7
- ISSN:
- 2056-9890
- Page Range / eLocation ID:
- 1018 to 1021
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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The title compound, C 10 H 13 NO 2 S, was synthesized by a nucleophilic substitution reaction between allyl amine and p -toluenesulfonyl chloride. The sulfonate S—O bond lengths are 1.4282 (17) and 1.4353 (17) Å, and the C—N—S—C torsion angle involving the sulfonamide moiety is −61.0 (2)°. In the crystal, centrosymmetric dimers of the title compound are present via intermolecular N—H...O hydrogen bonds between sulfonamide groups. These dimers are linked into ribbons along the c -axis direction through offset π–π interactions.more » « less
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The molecular structure of the title compound, C 11 H 15 NO 2 S, features a sulfonamide group with S=O bond lengths of 1.4357 (16) and 1.4349 (16) Å, an S—N bond length of 1.625 (2) Å, and an S—C bond length of 1.770 (2) Å. When viewing the molecule down the S—N bond, both N—C bonds of the pyrrolidine ring are oriented gauche to the S—C bond with torsion angles of −65.6 (2)° and 76.2 (2)°. The crystal structure features both intra- and intermolecular C—H...O hydrogen bonds, as well as intermolecular C—H...π and π–π interactions, leading to the formation of sheets parallel to the ac plane.more » « less
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In an attempt to grow 8-hydroxyquinoline–acetaminophen co-crystals from equimolar amounts of conformers in a chloroform–ethanol solvent mixture at room temperature, the title compound, C 9 H 7 NO, was obtained. The molecule is planar, with the hydroxy H atom forming an intramolecular O—H...N hydrogen bond. In the crystal, molecules form centrosymmetric dimers via two O—H...N hydrogen bonds. Thus, the hydroxy H atoms are involved in bifurcated O—H...N hydrogen bonds, leading to the formation of a central planar four-membered N 2 H 2 ring. The dimers are bound by intermolecular π–π stacking [the shortest C...C distance is 3.2997 (17) Å] and C—H...π interactions into a three-dimensional framework. The crystal grown represents a new monoclinic polymorph in the space group P 2 1 / n . The molecular structure of the present monoclinic polymorph is very similar to that of the orthorhombic polymorph (space group Fdd 2) studied previously [Roychowdhury et al. (1978). Acta Cryst. B 34 , 1047–1048; Banerjee & Saha (1986). Acta Cryst. C 42 , 1408–1411]. The structures of the two polymorphs are distinguished by the different geometries of the hydrogen-bonded dimers, which in the crystal of the orthorhombic polymorph possess twofold axis symmetry, with the central N 2 H 2 ring adopting a butterfly conformation.more » « less
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1107/S2056989020007185
