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Comparison of hydrogen bonds and diverse weak interactions of the nitro group in 2‐methyl‐4‐nitroanilinium nitrate, bisulfate and two hexafluoridosilicates: elementary graph‐set approach
Author(s) -
Daszkiewicz Marek,
Mielcarek Agnieszka
Publication year - 2016
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s2052520616016139
Subject(s) - hydrogen bond , nitro , nitrate , graph , set (abstract data type) , group (periodic table) , combinatorics , chemistry , mathematics , computational chemistry , molecule , computer science , organic chemistry , alkyl , programming language
Crystal structures of (H2m4na)NO 3 (1), (H2m4na)HSO 4 (2), (H2m4na) 2 SiF 6 (3) and (H2m4na) 2 SiF 6 ·2H 2 O (4), where 2m4na = 2‐methyl‐4‐nitroaniline, are presented. Two layers of interactions occur in the structures, N—H…O/F hydrogen bonds and interactions with the nitro group. Although diverse, hydrogen‐bonding patterns are compared with each other by means of interrelations among elementary graph‐set descriptors and descriptors of hydrogen‐bonding patterns. Using mathematical relations, the gradual expansion of the ring patterns was shown in the crystal structures. Parallel and perpendicular arranged nitro groups form weak π(N) NO2 …π(O) NO2 and π(N) NO2 …O NO2 interactions, respectively. The π NO2 …π ring interaction has an impact to the stabilization of parallel oriented nitro groups. Generally, weak interactions constructed by the nitro group occur in the studied crystals as follows: π(N) NO2 …π(O) NO2 , π ring …π ring , C—H…O (1); π(N) NO2 …π(O) NO2 , π(N) NO2 …O NO2 (2); π(N) NO2 …π(O) NO2 , π(N) NO2 …O NO2 (3); C—H…O (4).