Crystallographic and theoretical studies of 4,4′-dimethyl-7,7′-bi([1,2,5]thiadiazolo[3,4-b]pyridylidene)–chloranilic acid (1/1) with intermolecular O–H···N hydrogen bonds and S···O heteroatom interactions

Abstract

The molecular and crystal structure of a 1:1 co-crystal of 4,4 0 -dimethyl-7,7 0 -bi ([1,2,5]thiadiazolo [3,4-b] pyridylidene)-chloranilic acid, (1), has been determined by X-ray diffraction at the monoclinic space group P2 1 /c with cell parameters of a = 8.422(6), b = 7.343(4), c = 16.112(7) Å , b = 104.988(8)°, V = 962.5(10) Å 3 and Z = 2. In the crystal structure, two components connect via the intermolecular O-HÁÁÁN hydrogen bonds [2.804(4) Å ] and SÁÁÁO heteroatom interaction [2.945(3) Å ] with R 2 2 (7) couplings to form a unique and infinite one-dimensional supramolecular tape structure. The calculations of (1) at the HF/6-31G(d), MP2/6-31G(d), and B3LYP/6-31G(d) levels can almost reproduce X-ray geometry. In addition, the distances of the intermolecular O-HÁÁÁN and SÁÁÁO interactions by MP2/6-31G(d) and B3LYP/6-31G(d) levels agree well with those in the crystal. The calculated binding energies corrected BSSE and ZPE are -4.487 (HF), -7.473 (MP2), and -5.640 (B3LYP) kcal/mol. The results suggest that the complex (1) is very stable and the dispersion interaction is significantly important for the attractive intermolecular interaction in (1). The NBO analysis has revealed that the n(N) ? r*(O-H) interaction gives the strongest stabilization to the system and the major interaction for the intermolecular SÁÁÁO contact is n(O) ? r*(S-N).

A two-dimensional ladder-type network in the 2:1 co-crystal of 1,2,5-thiadiazole-3,4-dicarboxylic acid and 4,4′-bipyridine

“…Symmetry operators: a: -x, y, -z ? 1/2 (9) C7-C7 a 1.467 (8) C8-C9 1.377 (9) C1-C2 1.428 (7) C1-C3 1.503 (7) C2-C4 1.513 (7) C5-C6 1.359 (8) N3-C5 1.339 (9) O1-C3 1.292 (6) O2-C3 1.221 (6) O3-C4 1.220 (7) O4-C4 1.285 (8) [23,24] and no structure of thiadiazole derivatives with carboxyl group was found. To the best of our knowledge, this is the first example of a molecular ladder formed by intermolecular heteroatom interactions.…”

Interplay of thermochemistry and Structural Chemistry, the journal (volume 19, 2008) and the discipline

“…The next paper by Tomura et al [308] presented the preparation of a new 1:1 co-crystal of 4,4 0 -dimethyl-7,7 0 -bi([1, 2, 5]thiadiazolo[3,4,b]pyridylene) with chloranilic acid (2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone). The authors used X-ray diffraction to determine the molecular and crystal structure of this co-crystal and determined that the two components connect via intermolecular O-HÁÁÁN hydrogen bonds and SÁÁÁO heteroatom interactions to form an infinite one-dimensional supramolecular tape structure.…”