Molecular structures of cyclic sulfilimines without and with intramolecular sulfur-oxygen interaction: An x-ray study

J. Rábai, I. Kapovits, I. Jalsovszky, G. Argay, V. Fülöp, A. Kálmán, T. Koritsánszky

Research output: Contribution to journalArticle

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Abstract

3-Phenylbenzo[l.3,2]dithiazolium ylide 1.1 dioxide (1) and its o- methoxycarbonyl derivative (2) have been prepared and their structures established by X-ray crystallography from diffractometer data. Compound 1 (C12H9NO2S2) crystallizes in the triclinic space group PĪ with a=6.664(1), b=7.881(1), c=12.437(2) Å, α=98.81(1), β = 97.44(1), γ = 113.05(1)°, V = 580.9(4) Å3 Z = 2, D(c) = 1.51 g.cm-3 and μ(CuKα) = 4.00 mm-1. Compound 2 (C14H11NO4S2) crystallizes in the orthorhombic space group P212121, with a = 7.620(1), b = 8.887(1), c = 20.022(2) Å, V = 1355.9(5) Å3, Z = 4, D(c) = 1.57 g.cm-3 and μ(CuKα) = 3.65 mm-1. The crystal structures were solved by direct methods and refined to R = 0.062 for 1 and R = 0.028 for 2, using 1663 and 1424 observed reflections, respectively. In the cyclic N-sulfonyl sulfilimines 1 and 2 the characteristic bond distances and bond angles involving S(IV) and S(VI) atoms do not differ significantly from those found earlier for acyclic sulfilimines. Owing to S(IV)···O(carbonyl) close contact the sulfur(IV) atom in 2 exhibits a sulfuran-like configuration with almost linear (171°) N = S(IV)···O array (1.61 + 2.68 = 4.29 Å). The conformations of 1 and 2 have similar features. In both cases the five-membered dithiazolium ring is practically planar and the two aryl rings about sulfur(IV) atom are nearly perpendicular to the C(ar)-S(IV)-C(ar) plane ('butterfly conformation'). In contrast with acyclic sulfilimines, the benzene ring connected to S(VI) atom is constrained to be coplanar with the S(VI)-N S(IV) plane (Koch and Moffitt's case I of conjugation).

Original languageEnglish
Pages (from-to)13-21
Number of pages9
JournalJournal of Molecular Structure
Volume382
Issue number1
DOIs
Publication statusPublished - Aug 15 1996

Fingerprint

Molecular Structure
Sulfur
Molecular structure
Dilatation and Curettage
molecular structure
sulfur
X-Rays
Oxygen
X rays
Atoms
oxygen
atoms
Conformations
rings
Butterflies
x rays
X Ray Crystallography
interactions
Benzene
X ray crystallography

Keywords

  • Cyclic sulphilimines
  • Sulphur oxygen interaction
  • X-ray crystallography

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

Cite this

Molecular structures of cyclic sulfilimines without and with intramolecular sulfur-oxygen interaction : An x-ray study. / Rábai, J.; Kapovits, I.; Jalsovszky, I.; Argay, G.; Fülöp, V.; Kálmán, A.; Koritsánszky, T.

In: Journal of Molecular Structure, Vol. 382, No. 1, 15.08.1996, p. 13-21.

Research output: Contribution to journalArticle

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abstract = "3-Phenylbenzo[l.3,2]dithiazolium ylide 1.1 dioxide (1) and its o- methoxycarbonyl derivative (2) have been prepared and their structures established by X-ray crystallography from diffractometer data. Compound 1 (C12H9NO2S2) crystallizes in the triclinic space group PĪ with a=6.664(1), b=7.881(1), c=12.437(2) {\AA}, α=98.81(1), β = 97.44(1), γ = 113.05(1)°, V = 580.9(4) {\AA}3 Z = 2, D(c) = 1.51 g.cm-3 and μ(CuKα) = 4.00 mm-1. Compound 2 (C14H11NO4S2) crystallizes in the orthorhombic space group P212121, with a = 7.620(1), b = 8.887(1), c = 20.022(2) {\AA}, V = 1355.9(5) {\AA}3, Z = 4, D(c) = 1.57 g.cm-3 and μ(CuKα) = 3.65 mm-1. The crystal structures were solved by direct methods and refined to R = 0.062 for 1 and R = 0.028 for 2, using 1663 and 1424 observed reflections, respectively. In the cyclic N-sulfonyl sulfilimines 1 and 2 the characteristic bond distances and bond angles involving S(IV) and S(VI) atoms do not differ significantly from those found earlier for acyclic sulfilimines. Owing to S(IV)···O(carbonyl) close contact the sulfur(IV) atom in 2 exhibits a sulfuran-like configuration with almost linear (171°) N = S(IV)···O array (1.61 + 2.68 = 4.29 {\AA}). The conformations of 1 and 2 have similar features. In both cases the five-membered dithiazolium ring is practically planar and the two aryl rings about sulfur(IV) atom are nearly perpendicular to the C(ar)-S(IV)-C(ar) plane ('butterfly conformation'). In contrast with acyclic sulfilimines, the benzene ring connected to S(VI) atom is constrained to be coplanar with the S(VI)-N S(IV) plane (Koch and Moffitt's case I of conjugation).",
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AU - Kapovits, I.

AU - Jalsovszky, I.

AU - Argay, G.

AU - Fülöp, V.

AU - Kálmán, A.

AU - Koritsánszky, T.

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N2 - 3-Phenylbenzo[l.3,2]dithiazolium ylide 1.1 dioxide (1) and its o- methoxycarbonyl derivative (2) have been prepared and their structures established by X-ray crystallography from diffractometer data. Compound 1 (C12H9NO2S2) crystallizes in the triclinic space group PĪ with a=6.664(1), b=7.881(1), c=12.437(2) Å, α=98.81(1), β = 97.44(1), γ = 113.05(1)°, V = 580.9(4) Å3 Z = 2, D(c) = 1.51 g.cm-3 and μ(CuKα) = 4.00 mm-1. Compound 2 (C14H11NO4S2) crystallizes in the orthorhombic space group P212121, with a = 7.620(1), b = 8.887(1), c = 20.022(2) Å, V = 1355.9(5) Å3, Z = 4, D(c) = 1.57 g.cm-3 and μ(CuKα) = 3.65 mm-1. The crystal structures were solved by direct methods and refined to R = 0.062 for 1 and R = 0.028 for 2, using 1663 and 1424 observed reflections, respectively. In the cyclic N-sulfonyl sulfilimines 1 and 2 the characteristic bond distances and bond angles involving S(IV) and S(VI) atoms do not differ significantly from those found earlier for acyclic sulfilimines. Owing to S(IV)···O(carbonyl) close contact the sulfur(IV) atom in 2 exhibits a sulfuran-like configuration with almost linear (171°) N = S(IV)···O array (1.61 + 2.68 = 4.29 Å). The conformations of 1 and 2 have similar features. In both cases the five-membered dithiazolium ring is practically planar and the two aryl rings about sulfur(IV) atom are nearly perpendicular to the C(ar)-S(IV)-C(ar) plane ('butterfly conformation'). In contrast with acyclic sulfilimines, the benzene ring connected to S(VI) atom is constrained to be coplanar with the S(VI)-N S(IV) plane (Koch and Moffitt's case I of conjugation).

AB - 3-Phenylbenzo[l.3,2]dithiazolium ylide 1.1 dioxide (1) and its o- methoxycarbonyl derivative (2) have been prepared and their structures established by X-ray crystallography from diffractometer data. Compound 1 (C12H9NO2S2) crystallizes in the triclinic space group PĪ with a=6.664(1), b=7.881(1), c=12.437(2) Å, α=98.81(1), β = 97.44(1), γ = 113.05(1)°, V = 580.9(4) Å3 Z = 2, D(c) = 1.51 g.cm-3 and μ(CuKα) = 4.00 mm-1. Compound 2 (C14H11NO4S2) crystallizes in the orthorhombic space group P212121, with a = 7.620(1), b = 8.887(1), c = 20.022(2) Å, V = 1355.9(5) Å3, Z = 4, D(c) = 1.57 g.cm-3 and μ(CuKα) = 3.65 mm-1. The crystal structures were solved by direct methods and refined to R = 0.062 for 1 and R = 0.028 for 2, using 1663 and 1424 observed reflections, respectively. In the cyclic N-sulfonyl sulfilimines 1 and 2 the characteristic bond distances and bond angles involving S(IV) and S(VI) atoms do not differ significantly from those found earlier for acyclic sulfilimines. Owing to S(IV)···O(carbonyl) close contact the sulfur(IV) atom in 2 exhibits a sulfuran-like configuration with almost linear (171°) N = S(IV)···O array (1.61 + 2.68 = 4.29 Å). The conformations of 1 and 2 have similar features. In both cases the five-membered dithiazolium ring is practically planar and the two aryl rings about sulfur(IV) atom are nearly perpendicular to the C(ar)-S(IV)-C(ar) plane ('butterfly conformation'). In contrast with acyclic sulfilimines, the benzene ring connected to S(VI) atom is constrained to be coplanar with the S(VI)-N S(IV) plane (Koch and Moffitt's case I of conjugation).

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KW - Sulphur oxygen interaction

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