Acta Crystallographica Section B

Structural Science, Crystal Engineering and Materials

Volume 69, Part 2 (April 2013)

research papers

Acta Cryst. (2013). B69, 184-194    [ doi:10.1107/S2052519213002650 ]

Analysis of N-H...O hydrogen bonds in new C(O)-NH-P(O)-based phosphoric triamides and analogous structures deposited in the Cambridge Structural Database

M. Pourayoubi, M. Toghraee, V. Divjakovic, A. van der Lee, T. Mancilla Percino, M. A. Leyva Ramírez and A. Saneei

Abstract: Five new compounds belonging to the phosphoric triamide family have been synthesized: two of them with the formula XC(O)NHP(O)Y [X = CF3 (1) and CClF2 (2), Y = NHCH2C(CH3)2CH2NH] involving a 1,3-diazaphosphorinane ring part, and three 2,6-Cl2C6H3C(O)NHP(O)Z2 phosphoric triamides [Z = NHC(CH3)3 (3), N(CH3)(C6H11) (4) and N(CH3)(CH2C6H5) (5)]. The characterization was performed by 31P{1H}, 1H, 13C NMR, IR spectroscopy besides 19F NMR for fluorine containing compounds (1) and (2), and X-ray single-crystal structure analysis for (1), (3), (4) and (5). In each molecule the P atom has a distorted tetrahedral environment. The N atoms bonded to P atom have mainly sp2 character with a very slight tendency to a pyramidal coordination for some amido groups. Different types of N-H...O hydrogen bonds have been analyzed for (1), (3), (4) and (5) and 118 other structures (including 194 hydrogen bonds) deposited in the Cambridge Structural Database, containing either C(O)-NH-P(O)[N(C)(C)]2 or C(O)-NH-P(O)[NH(C)]2. The participation of NCP-H...O=P [NCP = the nitrogen atom of the C(O)-NH-P(O) fragment], N-H...O=P, N-H...O=C and NCP-H...O=C hydrogen bonds in different hydrogen-bonded motifs are discussed. Moreover, the involvement of the O atoms of C=O or P=O in the [NCP-H][N-H]...O=P, [N-H]2...O=P, [N-H]2...O=C and [N-H]3...O=C groups are considered. A histogram of N...O distances, the distribution of N-H...O angles and the scatterplot of N-H...O angles versus N...O distances are studied.

Keywords: hydrogen bonding; Cambridge Structural Database; crystal packing.

hkldisplay filedownload file

Structure factor file (CIF format) (97.2 kbytes)
[ doi:10.1107/S2052519213002650/dk5007Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (308.9 kbytes)
[ doi:10.1107/S2052519213002650/dk5007IIIsup3.hkl ]
Contains datablock III

hkldisplay filedownload file

Structure factor file (CIF format) (208.6 kbytes)
[ doi:10.1107/S2052519213002650/dk5007IVsup4.hkl ]
Contains datablock IV

hkldisplay filedownload file

Structure factor file (CIF format) (200.5 kbytes)
[ doi:10.1107/S2052519213002650/dk5007Vsup5.hkl ]
Contains datablock V


To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

 bibliographic record in  format

  Find reference:   Volume   Page   
  Search:     From   to      Advanced search

Copyright © International Union of Crystallography
IUCr Webmaster