Abstract
In the racemic title compound, C26H24N2O2S2, one of the thia-zine rings shows a twisted boat conformation (Q = 0.743 Å, θ = 92.1°) and the other a half-chair puckering (Q = 0.669 Å, θ = 54.3°). The terminal phenyl rings are almost parallel to each other [dihedral angle 21.71 (10)°]. Both of these rings are orthogonal to the central phenyl ring, subtending a dihedral angle of about 78° in each case. The extended structure is consolidated by C-H⋯O and C-H⋯S hydrogen bonds as well as aromatic ring inter-actions of parallel-displaced and T-type. The mol-ecule has approximate C2 local symmetry but this is not carried over to its three-dimensional structure or the inter-molecular inter-actions.
Highlights
In the racemic title compound, C26H24N2O2S2, one of the thiazine rings shows a twisted boat conformation (Q = 0.743 A, = 92.1) and the other a half-chair puckering (Q = 0.669 A, = 54.3)
Both of these rings are orthogonal to the central phenyl ring, subtending a dihedral angle of about 78 in each case
The extended structure is consolidated by C—HÁ Á ÁO and C—HÁ Á ÁS hydrogen bonds as well as aromatic ring interactions of parallel-displaced and T-type
Summary
Bis-heterocyclic compounds exhibit a variety of biological activities (Shaker, 2012). 2,20-(1,4-Phenylene)-bis-(3-phenyl1,3-thiazolidin-4-one), a phenylene-bridged bis-(1,3-thiazolidin-4-one) in which the bridging benzene ring is connected to C2 of each five-membered heterocycle, has been reported by three groups (Martani, 1956; Shaker, 1999; Mohammadi et al, 2020). 2,20-(1,4-Phenylene)-bis-(3-(4-fluorophenyl)-1,3thiazolidin-4-one) has shown good antifungal activity (AbdelRahman & Ali, 2013). Bis-heterocyclic compounds exhibit a variety of biological activities (Shaker, 2012). 2,20-(1,4-Phenylene)-bis-(3-phenyl1,3-thiazolidin-4-one), a phenylene-bridged bis-(1,3-thiazolidin-4-one) in which the bridging benzene ring is connected to C2 of each five-membered heterocycle, has been reported by three groups (Martani, 1956; Shaker, 1999; Mohammadi et al, 2020). The only report of a phenylene-bridged bis-(1,3-thiazin-4-one) in which the bridging benzene ring is connected to C2 of each six-membered heterocycle is of two unsaturated derivatives of 2,20-(1,4-phenylene)-bis-(3,4-dihydro-2H-1,3-thiazin-4-one) (Shaker et al, 2010). We have previously reported the synthesis and crystal structure of saturated meso-3,30-(1,4-phenylene)-bis-(2-phenyl-2,3,5,6tetrahydro-4H-1,3-thiazin-4-one), in which the bridging benzene ring is connected to the nitrogen atom of each heterocycle (Yennawar, Moyer & Silverburg, 2018). We report the synthesis and crystal structure of the racemic title compound, C26H24N2O2S2. Symmetry codes: (i) Àx þ 1; y þ 12; Àz þ 12; (ii) x þ 1; y; z; (iii) Àx þ 12; y þ 12; z
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