The 1:1 co-crystal of 2-bromo­naphthalene-1,4-dione and 1,8-di­hydroxy­anthracene-9,10-dione: crystal structure and Hirshfeld surface analysis

The asymmetric unit of the title co-crystal, C(10)H(5)BrO(2)·C(14)H(8)O(4) [systematic name: 2-bromo-1,4-di­hydro­naphthalene-1,4-dione–1,8-dihy­droxy-9,10-di­hydro­anthracene-9,10-dione (1/1)], features one mol­ecule of each coformer. The 2-bromo­naphtho­quinone mol­ecule is almost planar [r.m.s deviation of the 13 non-H atoms = 0.060 Å, with the maximum deviations of 0.093 (1) and 0.099 (1) Å being for the Br atom and a carbonyl-O atom, respectively]. The 1,8-di­hydroxy­anthra­quinone mol­ecule is planar (r.m.s. deviation for the 18 non-H atoms is 0.022 Å) and features two intra­molecular hy­droxy-O—H⋯O(carbon­yl) hydrogen bonds. Dimeric aggregates of 1,8-di­hydroxy­anthra­quinone mol­ecules assemble through weak inter­molecular hy­droxy-O—H⋯O(carbon­yl) hydrogen bonds. The mol­ecular packing comprises stacks of mol­ecules of 2-bromo­naphtho­quinone and dimeric assembles of 1,8-di­hydroxy­anthra­quinone with the shortest π–π contact within a stack of 3.5760 (9) Å occurring between the different rings of 2-bromo­naphtho­quinone mol­ecules. The analysis of the Hirshfeld surface reveals the importance of the inter­actions just indicated but, also the contribution of additional C—H⋯O contacts as well as C=O⋯π inter­actions to the mol­ecular packing.