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Isomeric nitrophthalimides: sheets built from N-H...O and C-H...O hydrogen bonds. 2004

Christopher Glidewell, and John N Low, and Janet M S Skakle, and James L Wardell
School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland. cg@st-andrews.ac.uk

Molecules of 3-nitrophthalimide, C(8)H(4)N(2)O(4), are linked into sheets by a combination of one N-H...O hydrogen bond [H...O = 1.99 angstroms, N...O = 2.8043 (14) angstroms and N-H...O = 176 degrees] and two independent C-H...O hydrogen bonds [H...O = 2.36 and 2.56 angstroms, C...O = 3.1639 (16) and 3.4386 (16) angstroms, and C-H...O = 142 and 153 degrees], and these sheets are linked into pairs by a single pi-pi stacking interaction. Molecules of isomeric 4-nitrophthalimide are linked into sheets by a combination of one three-centre N-H...(O)(2) hydrogen bond [H...O = 2.14 and 2.55 angstroms, N...O = 2.974 (3) and 3.231 (3) angstroms, N-H...O = 151 and 131 degrees, and O...H...O = 76 degrees] and two independent two-centre C-H...O hydrogen bonds [H...O = 2.38 and 2.54 angstroms, C...O = 3.257 (4) and 3.452 (4) angstroms, and C-H...O = 156 and 168 degrees].

UI MeSH Term Description Entries

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