Crystal structures and Hirshfeld surfaces of two 1,3-benzoxathiol-2-one derivatives

Eliza de L. Chazin, Paola de S. Sanches, Thatyana R. A. Vasconcelos, Claudia R. B. Gomes, James Wardell, William T. A. Harrison

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Abstract

The crystal structures of 6-meth­oxy-1,3-benzoxa­thiol-2-one, C9H8O3S, (I), and 2-oxo-1,3-benzoxa­thiol-6-yl acetate, C9H6O4S, (II), are described. Compound (I) is almost planar (r.m.s. deviation for the non-H atoms = 0.011 Å), whereas (II) shows a substantial twist between the fused-ring system and the acetate substituent [dihedral angle = 74.42 (3)°]. For both structures, the bond distances in the heterocyclic ring suggest that little if any conjugation occurs. In the crystal of (I), C—H...O hydrogen bonds link the mol­ecules into [1-11] chains incorporating alternating R22(8) and R22(12) inversion dimers. The extended structure of (II) features C(7) [201] chains linked by C—H...O hydrogen bonds, with further C—H...O bonds and weak π–π stacking inter­actions connecting the chains into a three-dimensional network. Hirshfeld fingerprint analyses for (I) and (II) are presented and discussed.
Original languageEnglish
Pages (from-to)78-82
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
VolumeE74
Issue number1
DOIs
Publication statusPublished - 1 Jan 2018

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Hydrogen bonds
Acetates
Crystal structure
methylidyne
Derivatives
crystal structure
acetates
Dihedral angle
Dimers
hydrogen bonds
rings
conjugation
Atoms
Crystals
Molecules
dihedral angle
dimers
inversions
deviation
crystals

Keywords

  • crystal structure
  • benzoxa­thiol-2-one
  • hydrogen bonds
  • Hirshfeld surface

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Crystal structures and Hirshfeld surfaces of two 1,3-benzoxathiol-2-one derivatives. / Chazin, Eliza de L.; Sanches, Paola de S.; Vasconcelos, Thatyana R. A.; Gomes, Claudia R. B.; Wardell, James; Harrison, William T. A.

In: Acta Crystallographica Section E: Crystallographic Communications, Vol. E74, No. 1, 01.01.2018, p. 78-82.

Research output: Contribution to journalArticle

Chazin, Eliza de L. ; Sanches, Paola de S. ; Vasconcelos, Thatyana R. A. ; Gomes, Claudia R. B. ; Wardell, James ; Harrison, William T. A. / Crystal structures and Hirshfeld surfaces of two 1,3-benzoxathiol-2-one derivatives. In: Acta Crystallographica Section E: Crystallographic Communications. 2018 ; Vol. E74, No. 1. pp. 78-82.
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title = "Crystal structures and Hirshfeld surfaces of two 1,3-benzoxathiol-2-one derivatives",
abstract = "The crystal structures of 6-meth­oxy-1,3-benzoxa­thiol-2-one, C9H8O3S, (I), and 2-oxo-1,3-benzoxa­thiol-6-yl acetate, C9H6O4S, (II), are described. Compound (I) is almost planar (r.m.s. deviation for the non-H atoms = 0.011 {\AA}), whereas (II) shows a substantial twist between the fused-ring system and the acetate substituent [dihedral angle = 74.42 (3)°]. For both structures, the bond distances in the heterocyclic ring suggest that little if any conjugation occurs. In the crystal of (I), C—H...O hydrogen bonds link the mol­ecules into [1-11] chains incorporating alternating R22(8) and R22(12) inversion dimers. The extended structure of (II) features C(7) [201] chains linked by C—H...O hydrogen bonds, with further C—H...O bonds and weak π–π stacking inter­actions connecting the chains into a three-dimensional network. Hirshfeld fingerprint analyses for (I) and (II) are presented and discussed.",
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T1 - Crystal structures and Hirshfeld surfaces of two 1,3-benzoxathiol-2-one derivatives

AU - Chazin, Eliza de L.

AU - Sanches, Paola de S.

AU - Vasconcelos, Thatyana R. A.

AU - Gomes, Claudia R. B.

AU - Wardell, James

AU - Harrison, William T. A.

N1 - Acknowledgements We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections.

PY - 2018/1/1

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N2 - The crystal structures of 6-meth­oxy-1,3-benzoxa­thiol-2-one, C9H8O3S, (I), and 2-oxo-1,3-benzoxa­thiol-6-yl acetate, C9H6O4S, (II), are described. Compound (I) is almost planar (r.m.s. deviation for the non-H atoms = 0.011 Å), whereas (II) shows a substantial twist between the fused-ring system and the acetate substituent [dihedral angle = 74.42 (3)°]. For both structures, the bond distances in the heterocyclic ring suggest that little if any conjugation occurs. In the crystal of (I), C—H...O hydrogen bonds link the mol­ecules into [1-11] chains incorporating alternating R22(8) and R22(12) inversion dimers. The extended structure of (II) features C(7) [201] chains linked by C—H...O hydrogen bonds, with further C—H...O bonds and weak π–π stacking inter­actions connecting the chains into a three-dimensional network. Hirshfeld fingerprint analyses for (I) and (II) are presented and discussed.

AB - The crystal structures of 6-meth­oxy-1,3-benzoxa­thiol-2-one, C9H8O3S, (I), and 2-oxo-1,3-benzoxa­thiol-6-yl acetate, C9H6O4S, (II), are described. Compound (I) is almost planar (r.m.s. deviation for the non-H atoms = 0.011 Å), whereas (II) shows a substantial twist between the fused-ring system and the acetate substituent [dihedral angle = 74.42 (3)°]. For both structures, the bond distances in the heterocyclic ring suggest that little if any conjugation occurs. In the crystal of (I), C—H...O hydrogen bonds link the mol­ecules into [1-11] chains incorporating alternating R22(8) and R22(12) inversion dimers. The extended structure of (II) features C(7) [201] chains linked by C—H...O hydrogen bonds, with further C—H...O bonds and weak π–π stacking inter­actions connecting the chains into a three-dimensional network. Hirshfeld fingerprint analyses for (I) and (II) are presented and discussed.

KW - crystal structure

KW - benzoxa­thiol-2-one

KW - hydrogen bonds

KW - Hirshfeld surface

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DO - 10.1107/S2056989017018072

M3 - Article

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SP - 78

EP - 82

JO - Acta Crystallographica Section E: Crystallographic Communications

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