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

doi:10.1107/S2056989017018072

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

Chemistry

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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 language	English
Pages (from-to)	78-82
Number of pages	5
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	E74
Issue number	1
DOIs	https://doi.org/10.1107/S2056989017018072
Publication status	Published - 1 Jan 2018

Bibliographical note

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

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
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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.",

keywords = "crystal structure, benzoxathiol-2-one, hydrogen bonds, Hirshfeld surface",

author = "Chazin, {Eliza de L.} and Sanches, {Paola de S.} and Vasconcelos, {Thatyana R. A.} and Gomes, {Claudia R. B.} and James Wardell and Harrison, {William T. A.}",

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

year = "2018",

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doi = "10.1107/S2056989017018072",

language = "English",

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TY - JOUR

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

Y1 - 2018/1/1

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

U2 - 10.1107/S2056989017018072

DO - 10.1107/S2056989017018072

M3 - Article

SN - 2056-9890

VL - E74

SP - 78

EP - 82

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

IS - 1

ER -

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

Abstract

Bibliographical note

Keywords

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