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Evaluation of N–H···O hydrogen bond interactions in two new phosphoric triamides with a P(O)[NHCH(CH3)2]2 segment by means of topological (AIM) calculations, Hirshfeld surface analysis and 3D energy framework approach

  • Atekeh Tarahhomi EMAIL logo , Arie van der Lee and Dan G. Dumitrescu
Published/Copyright: May 9, 2019
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 234 Issue 6

Abstract

Two new phosphoric triamides having a common part XP(O)[NHCH(CH3)2]2, with X =[2,3,6-F3–C6H2C(O)NH] (1) and [C6H11(CH3)N] (2), were prepared and characterized by spectroscopic techniques (FT-IR and 1H-, 13C-, 31P-NMR) and single crystal X-ray diffraction. The asymmetric unit of 1 is composed of one molecule, whereas for 2 it consists of six symmetry independent molecules. In all molecules, the P atoms are in a distorted tetrahedral environment of one oxygen and three nitrogen atoms. The latter have mainly sp2 character and a nearly planar environment. The crystal structures are stabilized via N–H · · · O hydrogen bond interactions, forming a linear arrangement for 1 and three independent parallel linear chains for 2, along the b and a axis, respectively. The intermolecular interactions in the molecular packing were analyzed using the Hirshfeld surface methodology, two-dimensional (2D) fingerprint plots and enrichment ratios (E). The prevalent interactions revealed by Hirshfeld surfaces are O · · · H type interactions for both structures 1 and 2, additionally C · · · O for 1 and H · · · H interactions for 2. The most favored contacts responsible for the molecular packing are C · · · F, N · · · H and O · · · H for 1 confirmed by E values greater than 1.30, whereas for 2, O · · · H and N · · · H intermolecular interactions with E values about 1.04 representing the favored contacts. Thus, the N–H · · · O hydrogen bond interactions are the dominant interactions in both compounds. For more details, a topological AIM analysis of N–H · · · O hydrogen bond interactions was performed: NCP–H · · · O=C hydrogen bond (the NCP is referred to the nitrogen atom within the C(O)NHP(O) segment) interactions in 1 are stronger than N–H · · · O=P interactions in both 1 and 2. Furthermore, a 3D topology of the molecular packing via the energy framework approach showed that the N–H · · · O hydrogen bond interactions in C(O)NHP(O)-based phosphoric triamide are predominantly electrostatic based, while they are electrostatic-dispersion based for other phosphoric triamides with a [N]P(O)[NH]2 skeleton.

Keywords: 3D energy framework; enrichment ratio; Hirshfeld surface analysis; N–H···O Hydrogen bond; phosphoric triamide

Acknowledgements

Support of this investigation by Semnan University is gratefully acknowledged.

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Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2019-0005).

Received: 2019-01-24
Accepted: 2019-04-10
Published Online: 2019-05-09
Published in Print: 2019-05-27

©2019 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Preparation, structural and spectroscopical properties of silver terbium diphosphate AgTbP2O7
  5. Crystal structure refinement of MnTe2, MnSe2, and MnS2: cation-anion and anion–anion bonding distances in pyrite-type structures
  6. The crystal structure of hibbingite, orthorhombic Fe2Cl(OH)3
  7. Mg[(UO2)2(Ge2O6(OH)2]·(H2O)4.4, a novel compound with mixed germanium coordination: cation disordering and topological features of β-U3O8 type sheets
  8. Polarized mapping Raman spectroscopy: identification of particle orientation in biominerals
  9. Organic and Metalorganic Crystal Structures
  10. Evaluation of N–H···O hydrogen bond interactions in two new phosphoric triamides with a P(O)[NHCH(CH3)2]2 segment by means of topological (AIM) calculations, Hirshfeld surface analysis and 3D energy framework approach
  11. Crystallographic Computing
  12. HKLF5Tools: a program for processing diffraction data of non-merohedrally twinned crystals
https://doi.org/10.1515/zkri-2019-0005
Keywords for this article
3D energy framework; enrichment ratio; Hirshfeld surface analysis; N–H···O Hydrogen bond; phosphoric triamide

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Preparation, structural and spectroscopical properties of silver terbium diphosphate AgTbP2O7
  5. Crystal structure refinement of MnTe2, MnSe2, and MnS2: cation-anion and anion–anion bonding distances in pyrite-type structures
  6. The crystal structure of hibbingite, orthorhombic Fe2Cl(OH)3
  7. Mg[(UO2)2(Ge2O6(OH)2]·(H2O)4.4, a novel compound with mixed germanium coordination: cation disordering and topological features of β-U3O8 type sheets
  8. Polarized mapping Raman spectroscopy: identification of particle orientation in biominerals
  9. Organic and Metalorganic Crystal Structures
  10. Evaluation of N–H···O hydrogen bond interactions in two new phosphoric triamides with a P(O)[NHCH(CH3)2]2 segment by means of topological (AIM) calculations, Hirshfeld surface analysis and 3D energy framework approach
  11. Crystallographic Computing
  12. HKLF5Tools: a program for processing diffraction data of non-merohedrally twinned crystals
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