Crystal structure of cis-7,8-dihy­droxy-5,10,15,20-tetra­phenyl­chlorin and its zinc(II)–ethyl­enedi­amine complex

The title chlorin, 2(Ph)H(2) , hydrogen-bonded to di­methyl­amino­pyridine (DMAP), C(44)H(32)N(4)O(2)·C(7)H(10)N(2), and its corresponding zinc(II) complex, 2(Ph)Zn, axially coordinated to ethyl­enedi­amine (EDA), [Zn(C(44)H(30)N(4)O(2))]·C(2)H(8)N(2), were isolated and crystallized by adventitious reduction of the corresponding osmate esters by DMAP and EDA, respectively. Known since 1996 and, inter alia, used for the preparation of a wide range of (planar and non-planar) chlorin analogues (so-called pyrrole-modified porphyrins), their conformational analyses in the solid state are important benchmarks. Both macrocycles are only modestly distorted from planarity and both are slightly more non-planar than the corresponding dimeth­oxy-derivative, but less planar than a free-base meso-penta­fluoro­phenyl-based osmate ester. NSD analyses provide qu­anti­tative and qualitative analyses of the distortion modes. One origin of the non-planarity is presumably the avoidance of the eclipsed configuration of the two vic–cis diols on the pyrroline moiety; the resulting deformation of the pyrroline translates in some cases into the macrocycle. The structure of 2(Ph)H(2) features voids making up ca 26% of the unit-cell volume filled with highly disordered solvate mol­ecules (chloro­form and hexa­nes). 2(Ph)Zn crystallized with a 13.6 (4)% occupied solvate methanol mol­ecule.