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
VL - E74
SP - 78
EP - 82
JO - Acta Crystallographica Section E: Crystallographic Communications
JF - Acta Crystallographica Section E: Crystallographic Communications
SN - 2056-9890
IS - 1
ER -