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A novel tubular hydrogen‐bond pattern in a new diazaphosphole oxide: a combination of X‐ray crystallography and theoretical study of hydrogen bonds
Author(s) -
Sabbaghi Fahimeh,
Pourayoubi Mehrdad,
Farhadipour Abolghasem,
Ghorbanian Nazila,
Andreev Pavel V.
Publication year - 2017
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s205322961700794x
Subject(s) - hydrogen bond , crystallography , natural bond orbital , molecule , hydrogen , ring (chemistry) , chemistry , low barrier hydrogen bond , hydrogen atom , group (periodic table) , organic chemistry
In the structure of 2‐(4‐chloroanilino)‐1,3,2λ 4 ‐diazaphosphol‐2‐one, C 12 H 11 ClN 3 OP, each molecule is connected with four neighbouring molecules through (N—H) 2 …O hydrogen bonds. These hydrogen bonds form a tubular arrangement along the [001] direction built from R 3 3 (12) and R 4 3 (14) hydrogen‐bond ring motifs, combined with a C (4) chain motif. The hole constructed in the tubular architecture includes a 12‐atom arrangement (three P, three N, three O and three H atoms) belonging to three adjacent molecules hydrogen bonded to each other. One of the N—H groups of the diazaphosphole ring, not co‐operating in classical hydrogen bonding, takes part in an N—H…π interaction. This interaction occurs within the tubular array and does not change the dimension of the hydrogen‐bond pattern. The energies of the N—H…O and N—H…π hydrogen bonds were studied by NBO (natural bond orbital) analysis, using the experimental hydrogen‐bonded cluster of molecules as the input file for the chemical calculations. In the 1 H NMR experiment, the nitrogen‐bound proton of the diazaphosphole ring has a high value of 17.2 Hz for the 2 J H–P coupling constant.