4,5-Bis(benzylthio)-1,3-dithiole-2-thione compounds: crystal structures of [(p-XC6H4CH2)(p-XC6H4CH2)dmit: X=Y=OMe; X=Y=NO2; and X=OMe, Y=NO2]

4,5-Bis(benzylthio)-1,3-dithiole-2-thiones, [(p-XC6H4CH2)(p-XC6H4CH2)dmit: X=Y=OMe (2); X=OMe, Y=NO2 (3); and X=NO2] (4)] have been prepared from benzyl chlorides and [NEt4]2[Zn(dmit)2]. Isostructural compounds, 2 and 3, crystallize in the triclinic space group \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document} $$P\bar 1$$ \end{document} (Z = 2) with a = 5.2920(10), b = 10.537(2), c = 18.961(4) Å, α = 102.79(3), β = 96.33(3), γ = 98.67(3)° for 2; a = 5.292(8), b = 10.528(12), c = 19.01(2) Å, α = 102.74(9), β = 96.26(11), γ = 98.56(11)° for 3. Compound 4 also crystallizes in the space group \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document} $$P\bar 1$$ \end{document} (Z = 4), with a = 9.296(8), b = 13.993(18), c = 16.186(4) Å, α = 106.68(3), β = 89.63(3), γ = 99.38(6)°. Molecular differences between 2 and 3, on one hand, and 4, on the other, arise in the disposition of the aryl rings relative to the dmit group. Short S---S contacts in 2 of 3.320(2) Å [S3---S3i (symmetry operation: i: −x + 1, −y + 1, −z)] and in 3 of 3.314(5) Å [S3---S3i (symmetry operation: i: −x + 1, −y, −z + 1)] link molecules into pairs. In 4, an S5A---S2B contact of 3.516(5) Å links two independent molecules, A and B, into bimolecular units, which are further connected into chains by S2A---S5Bi contacts (symmetry operation: i: x, y, z − 1) at 3.569(5) Å. C–H---O hydrogen bonds are also present in 3 and 4.