Acta Crystallographica Section C

Crystal Structure Communications

Volume 60, Part 2 (February 2004)

Acta Cryst. (2004). C60, o120-o124 [doi:10.1107/S0108270103027914]

-Stacked hydrogen-bonded dimers in 2-(2-nitrophenylaminocarbonyl)benzoic acid, and hydrogen-bonded sheets in orthorhombic and monoclinic polymorphs of 2-(4-nitrophenylaminocarbonyl)benzoic acid

C. Glidewell, J. N. Low, J. M. S. Skakle and J. L. Wardell

Abstract: Molecules of 2-(2-nitrophenylaminocarbonyl)benzoic acid, C₁₄H₁₀N₂O₅, are linked into centrosymmetric R ${_2^2}$ (8) dimers by a single O-HO hydrogen bond [HO = 1.78 Å, OO = 2.623 (2) Å and O-HO = 178°] and these dimers are linked into sheets by a single aromatic [bold pi] - stacking interaction. The isomeric compound 2-(4-nitrophenylaminocarbonyl)benzoic acid crystallizes in two polymorphic forms. In the orthorhombic form (space group P2₁2₁2₁ with Z' = 1, crystallized from ethanol), the molecules are linked into sheets of R ${_4^4}$ (22) rings by a combination of one N-HO hydrogen bond [HO = 1.96 Å, NO = 2.833 (3) Å and N-HO = 171°] and one O-HO hydrogen bond [HO = 1.78 Å, OO = 2.614 (3) Å and O-HO = 173°]. In the monoclinic form (space group P2₁/n with Z' = 2, crystallized from acetone), the molecules are linked by a combination of two N-HO hydrogen bonds [HO = 2.09 and 2.16 Å, NO = 2.873 (4) and 2.902 (3) Å, and N-HO = 147 and 141°] and two O-HO hydrogen bonds [HO = 1.84 and 1.83 Å, OO = 2.664 (3) and 2.666 (3) Å, and O-HO = 166 and 174°] into sheets of some complexity. These sheets are linked into a three-dimensional framework by a single C-HO hydrogen bond [HO = 2.45 Å, CO = 3.355 (4) Å and C-HO = 160°].

Formula: Isomers and polymorphs of C₁₄H₁₀N₂O₅

Online 10 January 2004


	Structure factor file (CIF format) (139.9 kbytes) Contains datablock I

	Structure factor file (CIF format) (89.6 kbytes) Contains datablock II

	Structure factor file (CIF format) (269.5 kbytes) Contains datablock III

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