Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Abstract

An evaluation of the Cambridge Structural Database for crystals containing Se … N secondary--bonding interactions was conducted. The presence of Se … N secondary-bonding interactions has been established in nearly 9% of crystals of mono-nuclear selenium compounds where such interactions can potentially form, that is, having at least one nitrogen atom. The Se … N interactions feature in 71 zero-dimensional, usually di-nuclear aggregates, 63 one-dimensional chains and tapes, and smaller numbers of two-and three-dimensional arrays, that is seven and one, respectively. Selenium(II) compounds form the majority of the dataset with only eight selenium(IV) compounds included in the survey. In most cases (112 out of 142), the selenium centre forms a single Se … N contact with 26 aggregates having a selenium atom forming two contacts and four examples where three Se … N contacts are evident. The great propensity of selenadiazole rings (75%) and selenocyanates (50%) to form Se … N secondary-bonding interactions in their crystals is particularly noteworthy.

Adducts of 2-Pyridylselenenyl Halides and Nitriles as Novel Supramolecular Building Blocks: Four-Center Se···N Chalcogen Bonding versus Other Weak Interactions

“…A similar Ch–N (Ch = S, Se, Te) structural motif is present in relative chalcogenadiazoles (Scheme ), which are important supramolecular building blocks which were extensively described in numerous reviews and research articles. ,,− …”

“…Found: C, 39.14; H, 3.85; N, 11.07 1. H NMR (700 MHz, D 2 O) δ 9.37 (d, J = 6.7 Hz, 1H, H5), 8.81 (d, J = 8.5 Hz, 1H, H8), 8.40 (t, J = 7.8 Hz, 1H, H7), 8.02 (t, J = 6.8 Hz, 1H, H6), 3.34 (q, J = 7.3 Hz, 2H, CH 2 ), 1.54 (t, J = 7.3 Hz, 3H, CH 3 ) 13. C{ 1 H} NMR δ 167.7 (C3), 160.1 (C9), 139.4 (C5), 135.9 (C8), 125.8 (C7), 122.9 (C6), 24.9 (CH 2 ), 8.9 (CH 3 ).2 O) δ 9.95 (d, J = 7.0 Hz, 1H, H5), 8.96 (d, J = 8.7 Hz, 1H, H8), 8.51 (t, J = 8.0 Hz, 1H, H7), 8.13 (t, J = 7.1 Hz, 1H, H6).…”

Exploring Supramolecular Assembly Space of Cationic 1,2,4-Selenodiazoles: Effect of the Substituent at the Carbon Atom and Anions

“…[ 13 , 14 , 15 , 16 ]. Chalcogenodiazoles have gained particular interest within ChB research and have been extensively studied in recent years in the context of their applications in anion recognition and as supramolecular building blocks [ 6 , 17 , 18 , 19 , 20 , 21 ].…”

A Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond

“…As shown in Figure 1, two N-Se•••N chalcogen bonds form a four-membered [Se−N] 2 cyclic homosynthon II. The homosynthon II and its analogues were frequently found in the structures of crystals involving 2,1,3benzoselenadiazoles or 1,2,5-chalcogenadiazoles [10][11][12][13]. In the homosynthon II, the N atom is an electron donor and the Se atom is an electron acceptor.…”