X-ray study of the hetero ring flexibility in saturated and partially saturated 3,1-benzoxazin-2-ones and 3,1-benzoxazine-2-thiones [1]. The structures of cis-4a,5,8,8a-tetrahydro-4H-3,1-benzoxazin-2(1H)-one, cis-4a,5,8,8a-tetrahydro-4H-3,1-benzoxazine-2(1H)-thione and cis-4a,5,6,7,8,8a-hexahydro-4H-3,1-benzoxazine-2(1H)-thione

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Abstract

The structures of the title compounds have been established by X-ray crystallography from diffractometer data. The crystals of the first (I), C8H11 NO2, are monoclinic space group P21/n, with a = 11.266(2), b = 9.638(1), c = 7.500(1) Å, β = 109.16(1)°, Z = 4, Dc = 1.323 g cm-3. The crystals of the second (II), C8H11NOS, are also monoclinic, space group P2,/n, with c = 7.681(1), b = 10.007(1), c = 11.207(1) Å, β = 106.06(1)°, Z = 4, Dc = 1.358 g cm-3. The crystals of the third (III), C8H12NOS, are orthorhombic, space group Pbca, with a = 11.862(8), b = 15.751(8), c = 18.375(8) Å, Z = 16, Dc = 1.325 g cm-3. The structures determined by direct methods have been refined to R = 0.037 for 1343 reflections of I, R = 0.038 for 1605 reflections of II, and R = 0.042 for 2595 of III. The conformations of the hetero rings have been compaired with the related 1-methyl-cis-4a,5,6,7,8,8a-hexahydro-4H-3,1-benzoxazine-2(1H)-thione (IV) [2]. The flexibility of the 2-oxo- and 2-thioxo derivatives of the 1,3-oxazine ring fused with different carbocycles is rather limited. The ring invariably assumes a conformation close to envelope 1E slightly distorted towards half-chair 3H6, which may be attributed to the intrinsic properties of these rings (e.g. the rather short endo C(2)O bond, etc.).

Original languageEnglish
Pages (from-to)31-43
Number of pages13
JournalJournal of Molecular Structure
Volume131
Issue number1-2
DOIs
Publication statusPublished - 1985

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Benzoxazines
Thiones
X Ray Crystallography
flexibility
X-Rays
X rays
Crystals
Conformations
rings
Oxazines
x rays
X ray crystallography
Diffractometers
crystals
diffractometers
seats
crystallography
Derivatives
envelopes
oxazine 1

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Materials Science (miscellaneous)
  • Atomic and Molecular Physics, and Optics

Cite this

@article{debb937bff344be887484e17bd140f92,
title = "X-ray study of the hetero ring flexibility in saturated and partially saturated 3,1-benzoxazin-2-ones and 3,1-benzoxazine-2-thiones [1]. The structures of cis-4a,5,8,8a-tetrahydro-4H-3,1-benzoxazin-2(1H)-one, cis-4a,5,8,8a-tetrahydro-4H-3,1-benzoxazine-2(1H)-thione and cis-4a,5,6,7,8,8a-hexahydro-4H-3,1-benzoxazine-2(1H)-thione",
abstract = "The structures of the title compounds have been established by X-ray crystallography from diffractometer data. The crystals of the first (I), C8H11 NO2, are monoclinic space group P21/n, with a = 11.266(2), b = 9.638(1), c = 7.500(1) {\AA}, β = 109.16(1)°, Z = 4, Dc = 1.323 g cm-3. The crystals of the second (II), C8H11NOS, are also monoclinic, space group P2,/n, with c = 7.681(1), b = 10.007(1), c = 11.207(1) {\AA}, β = 106.06(1)°, Z = 4, Dc = 1.358 g cm-3. The crystals of the third (III), C8H12NOS, are orthorhombic, space group Pbca, with a = 11.862(8), b = 15.751(8), c = 18.375(8) {\AA}, Z = 16, Dc = 1.325 g cm-3. The structures determined by direct methods have been refined to R = 0.037 for 1343 reflections of I, R = 0.038 for 1605 reflections of II, and R = 0.042 for 2595 of III. The conformations of the hetero rings have been compaired with the related 1-methyl-cis-4a,5,6,7,8,8a-hexahydro-4H-3,1-benzoxazine-2(1H)-thione (IV) [2]. The flexibility of the 2-oxo- and 2-thioxo derivatives of the 1,3-oxazine ring fused with different carbocycles is rather limited. The ring invariably assumes a conformation close to envelope 1E slightly distorted towards half-chair 3H6, which may be attributed to the intrinsic properties of these rings (e.g. the rather short endo C(2)O bond, etc.).",
author = "G. Argay and A. K{\'a}lm{\'a}n and {\'A} Kapor and G. St{\'a}jer and G. Bern{\'a}th",
year = "1985",
doi = "10.1016/0022-2860(85)85097-3",
language = "English",
volume = "131",
pages = "31--43",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",
number = "1-2",

}

TY - JOUR

T1 - X-ray study of the hetero ring flexibility in saturated and partially saturated 3,1-benzoxazin-2-ones and 3,1-benzoxazine-2-thiones [1]. The structures of cis-4a,5,8,8a-tetrahydro-4H-3,1-benzoxazin-2(1H)-one, cis-4a,5,8,8a-tetrahydro-4H-3,1-benzoxazine-2(1H)-thione and cis-4a,5,6,7,8,8a-hexahydro-4H-3,1-benzoxazine-2(1H)-thione

AU - Argay, G.

AU - Kálmán, A.

AU - Kapor, Á

AU - Stájer, G.

AU - Bernáth, G.

PY - 1985

Y1 - 1985

N2 - The structures of the title compounds have been established by X-ray crystallography from diffractometer data. The crystals of the first (I), C8H11 NO2, are monoclinic space group P21/n, with a = 11.266(2), b = 9.638(1), c = 7.500(1) Å, β = 109.16(1)°, Z = 4, Dc = 1.323 g cm-3. The crystals of the second (II), C8H11NOS, are also monoclinic, space group P2,/n, with c = 7.681(1), b = 10.007(1), c = 11.207(1) Å, β = 106.06(1)°, Z = 4, Dc = 1.358 g cm-3. The crystals of the third (III), C8H12NOS, are orthorhombic, space group Pbca, with a = 11.862(8), b = 15.751(8), c = 18.375(8) Å, Z = 16, Dc = 1.325 g cm-3. The structures determined by direct methods have been refined to R = 0.037 for 1343 reflections of I, R = 0.038 for 1605 reflections of II, and R = 0.042 for 2595 of III. The conformations of the hetero rings have been compaired with the related 1-methyl-cis-4a,5,6,7,8,8a-hexahydro-4H-3,1-benzoxazine-2(1H)-thione (IV) [2]. The flexibility of the 2-oxo- and 2-thioxo derivatives of the 1,3-oxazine ring fused with different carbocycles is rather limited. The ring invariably assumes a conformation close to envelope 1E slightly distorted towards half-chair 3H6, which may be attributed to the intrinsic properties of these rings (e.g. the rather short endo C(2)O bond, etc.).

AB - The structures of the title compounds have been established by X-ray crystallography from diffractometer data. The crystals of the first (I), C8H11 NO2, are monoclinic space group P21/n, with a = 11.266(2), b = 9.638(1), c = 7.500(1) Å, β = 109.16(1)°, Z = 4, Dc = 1.323 g cm-3. The crystals of the second (II), C8H11NOS, are also monoclinic, space group P2,/n, with c = 7.681(1), b = 10.007(1), c = 11.207(1) Å, β = 106.06(1)°, Z = 4, Dc = 1.358 g cm-3. The crystals of the third (III), C8H12NOS, are orthorhombic, space group Pbca, with a = 11.862(8), b = 15.751(8), c = 18.375(8) Å, Z = 16, Dc = 1.325 g cm-3. The structures determined by direct methods have been refined to R = 0.037 for 1343 reflections of I, R = 0.038 for 1605 reflections of II, and R = 0.042 for 2595 of III. The conformations of the hetero rings have been compaired with the related 1-methyl-cis-4a,5,6,7,8,8a-hexahydro-4H-3,1-benzoxazine-2(1H)-thione (IV) [2]. The flexibility of the 2-oxo- and 2-thioxo derivatives of the 1,3-oxazine ring fused with different carbocycles is rather limited. The ring invariably assumes a conformation close to envelope 1E slightly distorted towards half-chair 3H6, which may be attributed to the intrinsic properties of these rings (e.g. the rather short endo C(2)O bond, etc.).

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U2 - 10.1016/0022-2860(85)85097-3

DO - 10.1016/0022-2860(85)85097-3

M3 - Article

AN - SCOPUS:3242861703

VL - 131

SP - 31

EP - 43

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

IS - 1-2

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