TY - JOUR
T1 - Co-crystals of an organic triselenocyanate with ditopic Lewis bases
T2 - recurrent chalcogen bond interactions motifs
AU - Riel, Asia Marie S.
AU - Jeannin, Olivier
AU - Berryman, Orion B.
AU - Fourmigué, Marc
N1 - Publisher Copyright:
© International Union of Crystallography, 2019
PY - 2019/2/1
Y1 - 2019/2/1
N2 - Organic selenocyanates R–Se–CN can act as an amphoteric chalcogen bond (ChB) donor (through the Se atom) and acceptor (through the N atom lone pair). Co-crystallization of tri-substituted 1,3,5-tris(selenocyanatomethyl)-2,4,6-trimethylbenzene (1) is investigated with different ditopic Lewis bases acting as chalcogen bond (ChB) acceptors to investigate the outcome of the competition, as ChB acceptor, between the nitrogen lone pair of the SeCN group and other Lewis bases involving pyridinyl or carbonyl functions. In the presence of tetramethylpyrazine (TMP), benzoquinone (BQ) and para-dinitrobenzene (pDNB) as ditopic Lewis bases, a recurrent oligomeric motif stabilized by six ChB interactions is observed, involving six SeCN groups and the ChB acceptor sites of TMP, BQ and pDNB in the 2:1 adducts (1) 2 ·TMP, (1) 2 ·BQ and (1) 2 ·pDNB.
AB - Organic selenocyanates R–Se–CN can act as an amphoteric chalcogen bond (ChB) donor (through the Se atom) and acceptor (through the N atom lone pair). Co-crystallization of tri-substituted 1,3,5-tris(selenocyanatomethyl)-2,4,6-trimethylbenzene (1) is investigated with different ditopic Lewis bases acting as chalcogen bond (ChB) acceptors to investigate the outcome of the competition, as ChB acceptor, between the nitrogen lone pair of the SeCN group and other Lewis bases involving pyridinyl or carbonyl functions. In the presence of tetramethylpyrazine (TMP), benzoquinone (BQ) and para-dinitrobenzene (pDNB) as ditopic Lewis bases, a recurrent oligomeric motif stabilized by six ChB interactions is observed, involving six SeCN groups and the ChB acceptor sites of TMP, BQ and pDNB in the 2:1 adducts (1) 2 ·TMP, (1) 2 ·BQ and (1) 2 ·pDNB.
KW - chalcogen bond
KW - sigma-hole interactions
UR - http://www.scopus.com/inward/record.url?scp=85060491694&partnerID=8YFLogxK
U2 - 10.1107/S2052520618017778
DO - 10.1107/S2052520618017778
M3 - Article
C2 - 32830775
AN - SCOPUS:85060491694
SN - 2052-5192
VL - 75
SP - 34
EP - 38
JO - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
JF - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
IS - 1
ER -