Three new phosphoric triamides with a [C(O)NH]P(O)[N(C)(C)]2 skeleton: a database analysis of C—N—C and P—N—C bond angles. Issue 10 (15th October 2014)

• Record Type: Journal Article
• Authors: Pourayoubi, Mehrdad; Tarahhomi, Atekeh; Rheingold, Arnold L.; Golen, James A.
• Is Part Of: Acta crystallographica. Volume 70:Issue 10(2014:Oct.)
• Page Start: 998
• Page End: 1002
• Publication Date: 2014-10-15
• Subjects: Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229614020488
• Languages: English
• ISSNs: 2053-2296

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>In <italic>N</italic>, <italic>N</italic>, <italic>N</italic>′, <italic>N</italic>′‐tetraethyl‐<italic>N</italic>′′‐(4‐fluorobenzoyl)phosphoric triamide, C<sub>15</sub>H<sub>25</sub>FN<sub>3</sub>O<sub>2</sub>P, (I), and <italic>N</italic>‐(2, 6‐difluorobenzoyl)‐<italic>N</italic>′, <italic>N</italic>′′‐bis(4‐methylpiperidin‐1‐yl)phosphoric triamide, C<sub>19</sub>H<sub>28</sub>F<sub>2</sub>N<sub>3</sub>O<sub>2</sub>P, (II), the C—N—C angle at each tertiary N atom is significantly smaller than the two P—N—C angles. For the other new structure, <italic>N</italic>, <italic>N</italic>′‐dicyclohexyl‐<italic>N</italic>′′‐(2‐fluorobenzoyl)‐<italic>N</italic>, <italic>N</italic>′‐dimethylphosphoric triamide, C<sub>21</sub>H<sub>33</sub>FN<sub>3</sub>O<sub>2</sub>P, (III), one C—N—C angle [117.08 (12)°] has a greater value than the related P—N—C angle [115.59 (9)°] at the same N atom. Furthermore, for most of the analogous structures with a [C(=O)NH]P(=O)[N(C)(C)]<sub>2</sub> skeleton deposited in the Cambridge Structural Database [CSD; Allen (2002). <italic>Acta Cryst.</italic> B<bold>58</bold>, 380–388], the C—N—C angle is significantly smaller than the two P—N—C angles; exceptions were found for four structures with the <italic>N</italic>‐methylcyclohexylamide substituent, similar to (III), one structure with the seven‐membered cyclic amide azepan‐1‐yl substituent and one structure with an <italic>N</italic>‐methylbenzylamide substituent. The asymmetric units of (I), (II) and (III) contain one molecule, and in the crystal structures, adjacent molecules are linked <italic>via</italic> pairs of N—H...O=P hydrogen bonds to form dimers.</p> </abstract>