C–H ⋯ N mediated hexagonal network in the crystal structure of the 1 : 1 molecular complex 1,3,5-tricyanobenzene–hexamethylbenzene

Abstract

Molecules of 1,3,5-tricyanobenzene are networked with C-H...N hydrogen bonds into a symmetrical hexagonal pattern in the crystal structure of the 1 : 1 complex formed by the compound with hexamethylbenzene. structure of pure 3 itself but in general, layering of a planar aromatic hydrocarbon is difficult and the crystal structure of pure 3 is exceptional.15 Retrieval of all hexamethylbenzene containing structures from the Cambridge Structural Data-base16 (1992 release, version 5 , 102589 entries) yielded ten hits (no metal atom) but in many of these, the molecules of 3 are arranged in a herringbone or quasi-herringbone fashion. 15

Cyanoferrocene: a Two-Dimensional Network Generated by Short C—H.N Hydrogen Bonds

“…(iii), and from atom C24 1 in the molecule at (1-x, i + y, 3_ z), i.e. o(iv), with C...N distances of 3.384(6) and 3.381 (6)A, respectively, which are significantly shorter than those observed in cyanobenzenes (Fauvet, Massaux & Chevalier, 1978;Guth, Heger & Drtick, 1982;Reddy, Goud, Panneerselvam & Desiraju, 1993); the corresponding N...H distances (based onfiding H atoms, with C--H 0.93 ,~) are 2.70 and 3.00 A, respectively (Table 3). The second of these probably represents a rather weak interaction despite the similar C...N distance.…”

“…Simple cyanobenzenes often exhibit intermolecular C---H...N--C hydrogen bonds in the solid state and examples include benzonitrile (C6H5CN), where the intermolecular C...N distance across the hydrogen bond is 3.51 (1),~ (Fauvet, Massaux & Chevalier, 1978), 1,4-dicyanobenzene, where the corresponding distance is also 3.51 (1) A (Guth, Heger & Driick, 1982), 1,3,5-tricyanobenzene in its 1:1 molecular complex with hexamethylbenzene, where the tricyanobenzene forms discrete layers interleaved with layers of hexamethylbenzene and in which there are four intermolecular C...N distances of 3.471 (4) and two of 3.516 (6) ,~ (Reddy, Goud, Panneerselvam & Desiraju, 1993), and 1,2,4,5-tetracyanobenzene, in which each of the four independent N atoms forms several close intermolecular C...N contacts (Prout & Tickle, 1973), although the precision of this determination, from visually estimated photographic data, is not high. The cyclopentadienyl rings in ferrocene are more electron rich than benzene rings, thus allowing the possibility of a higher negative charge on the N atom of a cyano substituent on the C5 ring, as compared with the N atom of a cyanobenzene moiety.…”

Two-dimensional hydrogen-bonded networks based on bent oxadiazole bridging organic spacers

“…Very recently, an actinide-organic framework, namely [(Th 2 F 5 )(NC 7 3 ], was reported, wherein the Th(IV) atom is part of framework instead of being the guest anion [8]. So far, the use of organoammonium cations as the structure-directing agents for oxide phases and inorganic halides are well documented [3,9], and several organically templated (based on bipyridium) organic-inorganic supramolecular complexes, such as (4,4 0 -H 2 bipy)(Mo 7 [3], were reported. To the best of our knowledge, compound 1 reported herein is the first protonated 2,5-bis(4-pyridyl)-1,3,4-oxadiazole templated supramolecular actinide complex.…”

“…Colorless crystals of 1 were grown by carefully layering a CH 3 CN solution of Th(NO 3 ) 4 AE 4H 2 O onto a CH 2 Cl 2 solution of L1 under ambient conditions [6]. In 1, the bent ligand L1 is protonated on one para-N terminus, and then linked by N- [7]. These two-dimensional nets are stacked together along the crystallographic a-axis to generate a porous network (Fig.…”

Molecular Recognition Induced Supramolecular Array of 2-Aminopyrimidine with Terephthalic Acid, 1,4-Phenylenediacetic Acid and Fumaric Acid in Solid State via H-bonding and π-stacking Interactions*

“…The crystal structures of molecular complexes of 2-aminopyximidine (ZAP) with terephthalic acid (1) (1 : 1; Complex A), 1,4-phenylenediacetic acid (2) (1 : 1; Complex B) and fumaric acid (3) (1:2;Complex C) were determined. Complex A is orthorhombic, space group Pnpla, with a = 13.0323 (3) (2), c = 20.1621(4) A; a = j ¶ = y = 90' ; Z = 4; Dcllc = 1.323 Mg/m3; final R = 0.0461, wR2 = 0.1158 for 1662 independent reflections.…”