Crystal and Molecular Structure of 2,5-Bis(2′-hydroxyethylamino)-1,4-benzoquinone

Abstract

Crystals of 2,5-bis(2′-hydroxyethylamino)-1,4-benzoquinone are monoclinic, a = 5.020(1), b = 19.238(3), c = 5.214(1) Å, β = 96.15(3)°, Z = 2, space group P21/n. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to a final R of 0.045 for 646 reflections with I ≥ 3σ(I). The benzoquinone ring in the centrosymmetric molecule is slightly, but significantly, nonplanar. Bond distances in the compound (C—C, 1.247 (2) and 1.410 (3), C—N, 1.332 (3) and 1.457 (3), C—C, 1.384–1.514 (3), N—H, 0.89 (3), O—H, 1.07 (5), and C—H, 0.95–1.09 (3) Å) are similar to those in related compounds. The structure features an extensive network of N—H … O (N … O = 2.639 (3) and 3.033 (2) Å) and O—H … O(O … O = 2.757 (3) Å ) hydrogen bonds.