Acta Crystallographica, Section C: Crystal Structure Communications p. o265-o272 (2011)
Update date:2022-08-02
Topics:
Pourayoubi, Mehrdad
Tarahhomi, Atekeh
Saneei, Anahid
Rheingold, Arnold L.
Golen, James A.
In the crystal networks of N,N′-bis-(2-chloro-benzyl)- N′′-(2,6-difluoro-benzo-yl)phosphor-ic triamide, C 21H18Cl2F2N3O 2P, (I), N-(2,6-difluoro-benzo-yl)-N′,N′′-bis-(4- meth-oxy-benzyl)phosphor-ic triamide, C23H24F 2N3O4P, (II), and N-(2-chloro-2,2-difluoro- acetyl)-N′,N′′-bis-(4-methyl-phenyl)phosphor-ic tri-amide, C16H17ClF2N3O2P, (III), C=O...H-NC(O)NHP(O) and P=O...H-Namide hydrogen bonds are responsible for the aggregation of the mol-ecules. This is the opposite result from that commonly observed for carbacyl-amido-phosphates, which show a tendency for the phosphoryl group, rather than the carbonyl counterpart, to form hydrogen bonds with the NH group of the C(O)NHP(O) skeleton. This hydrogen-bond pattern leads to cyclic R2 2(10) motifs in (I)-(III), different from those found for all previously reported compounds of the general formula RC(O)NHP(O)[NR 1 R 2]2 with the syn orientation of P=O versus NH [R2 2(8)], and also from those commonly observed for RC(O)NHP(O)[NHR 1]2 [a sequence of alternate R 2 2(8) and R2 2(12) motifs]. In these cases, the R2 2(8) and R2 2(12) graph sets are formed through similar kinds of hydrogen bond, i.e. a pair of P=O...H-NC(O)NHP(O) hydrogen bonds for the former and two C=O...H-Namide hydrogen bonds for the latter. This article also reviews 102 similar structures deposited in the Cambridge Structural Database and with the Inter-national Union of Crystallography, with the aim of comparing hydrogen-bond strengths in the above-mentioned cyclic motifs. This analysis shows that the strongest N-H...O hydrogen bonds exist in the R2 2(8) rings of some mol-ecules. The phosphoryl and carbonyl groups in each of compounds (I)-(III) are anti with respect to each other and the P atoms are in a tetra-hedral coordination environment. In the crystal structures, adjacent mol-ecules are linked via the above-mentioned hydrogen bonds in a linear arrangement, parallel to [010] for (I) and (III) and parallel to [100] for (II). Formation of the NC(O)NHP(O)-H...O=C instead of the NC(O)NHP(O)- H...O=P hydrogen bond is reflected in the higher NC(O)NHP(O)-H vibrational frequencies for these mol-ecules compared with previously reported analogous compounds.
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