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The title compound, C15H11Cl2NO, was synthesized from N-­benzyl­isatin. The compound crystallizes as stacks of mol­ecules running down the c axis. Mol­ecules within each of these stacks inter­act with each other through π–π and C—H...π inter­actions, and inter­act with neighbouring stacks through C—H...O inter­actions.

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The title compound, C20H19NO5S2, crystallizes as an almost 2:1 mixture of two mol­ecular orientations (described as Orient-A and Orient-B). The consequences of these two orientations is the formation of three types of N—H...O hydrogen-bonded dimers in which the (Orient-A + Orient-A) dimers are likely to be the most stable, while the mixed (Orient-A + Orient-B) dimers are more frequent. Extra inter­actions in the form of C—H...O and C—H...π inter­actions act to further stabilize these dimers and probably allow the less energetically favourable (Orient-A + Orient-B) and (Orient-B + Orient-B) hydrogen-bonded dimers to exist by preventing their conversion to (Orient-A + Orient-A)-only hydrogen-bonded dimers during the crystal-growth process.
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