Derivatives of benzimidazolene-2-thione differing in
substitution at the 4 and 5 positions
have been synthesized and studied by single-crystal X-ray diffraction
and/or X-ray powder
diffraction. These derivatives include five monosubstituted
compounds (1-SX; X = Me, F,
Cl, Br, I), four disubstituted compounds
(1-SX
2
; X = Me, F, Cl, Br), the
parent dihydro
compound (1-SH
2
), and the naphthyl
compound (2-SH
2
). Five of these
molecules gave
crystals suitable for single-crystal X-ray diffraction. In all of
these crystals, the molecules
pack as parallel, hydrogen-bonded tapes. Alternate molecules of a
tape occupy two different
planes that are separated by approximately 1 Å. The resulting
structure is named a stepped
tape. These stepped tapes are divided into two classes based
on packing: tapes of
1-SH
2
,
1-SMe
2
, and 1-SF pack in
flat, parallel planes. Tapes of
2-SH
2
,
1-SF
2
, and
1-SCl
2
pack at
an angle; of these, two (2-SH
2
and
1-SF
2
) incorporate molecules of
solvent. None of the
structures is isomorphic.
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