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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Crystal structure of tert -butyl 3,6-diiodocarbazole-9-carboxylate
The molecular structure of tert -butyl 3,6-diiodocarbazole-9-carboxylate, C 17 H 15 I 2 NO 2 , features a nearly planar 13-membered carbazole ring with C—I bond lengths of 2.092 (4) and 2.104 (4) Å. The carbamate group has key bond lengths of 1.404 (6) Å (N—C), 1.330 (5) Å (O—C), and 1.201 (6) Å (C=O). The crystal contains intermolecular π–π interactions, as well as both type I and type II intermolecular I...I interactions.
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- NSF-PAR ID:
- 10429125
- Date Published:
- Journal Name:
- Acta Crystallographica Section E Crystallographic Communications
- Volume:
- 79
- Issue:
- 4
- ISSN:
- 2056-9890
- Page Range / eLocation ID:
- 345 to 348
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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The structure of zymonic acid (systematic name: 4-hydroxy-2-methyl-5-oxo-2,5-dihydrofuran-2-carboxylic acid), C 6 H 6 O 5 , which had previously eluded crystallographic determination, is presented here for the first time. It forms by intramolecular condensation of parapyruvic acid, which is the product of aldol condensation of pyruvic acid. A redetermination of the crystal structure of pyruvic acid (systematic name: 2-oxopropanoic acid), C 3 H 4 O 3 , at low temperature (90 K) and with increased precision, is also presented [for the previous structure, see: Harata et al. (1977). Acta Cryst. B 33 , 210–212]. In zymonic acid, the hydroxylactone ring is close to planar (r.m.s. deviation = 0.0108 Å) and the dihedral angle between the ring and the plane formed by the bonds of the methyl and carboxylic acid carbon atoms to the ring is 88.68 (7)°. The torsion angle of the carboxylic acid group relative to the ring is 12.04 (16)°. The pyruvic acid molecule is almost planar, having a dihedral angle between the carboxylic acid and methyl-ketone groups of 3.95 (6)°. Intermolecular interactions in both crystal structures are dominated by hydrogen bonding. The common R 2 2 (8) hydrogen-bonding motif links carboxylic acid groups on adjacent molecules in both structures. In zymonic acid, this results in dimers about a crystallographic twofold of space group C 2/ c , which forces the carboxylic acid group to be disordered exactly 50:50, which scrambles the carbonyl and hydroxyl groups and gives an apparent equalization of the C—O bond lengths [1.2568 (16) and 1.2602 (16) Å]. The other hydrogen bonds in zymonic acid (O—H...O and weak C—H...O), link molecules across a 2 1 -screw axis, and generate an R 2 2 (9) motif. These hydrogen-bonding interactions propagate to form extended pleated sheets in the ab plane. Stacking of these zigzag sheets along c involves only van der Waals contacts. In pyruvic acid, inversion-related molecules are linked into R 2 2 (8) dimers, with van der Waals interactions between dimers as the only other intermolecular contacts.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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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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null (Ed.)The syntheses and crystal structures of the two title compounds, C 11 H 10 O 3 ( I ) and C 17 H 14 BrNO 2 ( II ), both containing the bicyclo[2.2.2]octene ring system, are reported here [the structure of I has been reported previously: White & Goh (2014). Private Communication (refcode HOKRIK). CCDC, Cambridge, England]. The bond lengths and angles of the bicyclo[2.2.2]octene ring system are similar for both structures. The imide functional group of II features carbonyl C=O bond lengths of 1.209 (2) and 1.210 (2) Å, with C—N bond lengths of 1.393 (2) and 1.397 (2) Å. The five-membered imide ring is nearly planar, and it is positioned exo relative to the alkene bridgehead carbon atoms of the bicyclo[2.2.2]octene ring system. Non-covalent interactions present in the crystal structure of II include a number of C—H...O interactions. The extended structure of II also features C—H...O hydrogen bonds as well as C—H...π and lone pair–π interactions, which combine together to create supramolecular sheets.more » « less
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1107/S205698902300230X
