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The title mol­ecule, C19H12S2O2, lies on a twofold rotation axis. The thio­chromonone unit is essentially planar, with a maximum deviation of 0.0491 (14) Å. The dihedral angle between the thio­chromenone ring systems is 64.48 (4)°. In the crystal, there are weak π–π stacking inter­actions, with a centroid–centroid distance of 3.7147 (9) Å.

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In the racemic title compound, C21H18O4, the chromone ring is essentially planar [maximum deviation from the least-squares plane = 0.026 (3) Å], with a dihedral angle of 78.18 (12)° between the benzene rings of the chromanone and chromenone moieties. In the crystal, there are weak π–π stacking inter­actions [minimum ring centroid separation = 3.9286 (17) Å].

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In the title compound, C13H12Cl2O4S, both C=C double bonds adopt an E conformation. The S atom has a distorted tetra­hedral geometry with bond angles ranging from 103.03 (12) to 118.12 (13)°. The eth­oxy­carbonyl group is disordered over two sets of sites, with site-occupancy factors of 0.739 (11) and 0.261 (11). In the crystal, C—H...O inter­actions link the mol­ecules into chains mol­ecules running parallel to the a axis.
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