A new Z′=(2+0.5+0.5) amidophosphoester structure: Hirshfeld surface analysis of symmetry-independent molecules
-
Mojtaba Keikha
,
Atekeh Tarahhomi
Abstract
Tetraethyl 1,3-phenylenebis(phosphoramidate) was synthesized and characterized by 1H, 13C, 31P NMR, IR and mass spectroscopies. The asymmetric unit is composed of two half-molecules, each residing on a two-fold axis, and two complete molecules, thus leading to a Z′=(2+0.5+0.5)=3 structure. The most plausible explanation for the occurrence of multiple independent molecules is a frustration between relatively strong hydrogen bond interactions and weaker CH···π interactions. In each of the molecules, the P atoms are in a similar distorted tetrahedral environment. The N atoms bonded to P atoms have mainly sp2 character tending towards a planar environment. In the crystal structure, the phosphoryl O atoms are involved in classical N–H···O=P and weaker C–H···O=P hydrogen bonds as (N–H)(C–H) ···O=P, acting as a double hydrogen-bond acceptor. These hydrogen bonds along with other C–H···O hydrogen bonds and C–H···π interactions create a 3D crystalline network. Hirshfeld surfaces and two-dimensional (2D) fingerprint plots are calculated for analyzing intermolecular interactions in each of the independent molecules of the title compound. For all four independent molecules, the contribution of H···H contacts to the total interactions is decisive, being larger than 60% for each molecule. The O···H/H···O contacts are the characteristic intermolecular contacts in the corresponding molecules. Furthermore, the C···H/H···C, including the C–H···π interactions, and N···H/H···N contacts cover other intermolecular contacts in the crystal lattice.
Acknowledgements
Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.
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Supplemental Material:
The online version of this article offers supplementary material (DOI: https://doi.org/10.1515/zkri-2016-2032).
©2017 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
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- Graphical Synopsis
- Inorganic Crystal Structures
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- Crystal packing and layered morphology relationships in naphthalene sulfonate compounds
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Artikel in diesem Heft
- Frontmatter
- Graphical Synopsis
- Inorganic Crystal Structures
- Synthesis and characterization of [Cu(salen)]2 coordination nano-assembly by a green and simple method
- High-temperature phase transitions and domain structures of KLiSO4: studied by polarisation-optics, X-ray topography and liquid–crystal surface decoration
- The germanides Er5Pd4Ge8 and Tm5Pd4Ge8 – 3D [Pd4Ge8] polyanions with Ge2 dumb-bells and Ge4 chains in cis-conformation
- Organic and Metalorganic Crystal Structures
- Planarity of substituted pyrrole and furan rings in (3R*, 1′S*, 3′R*)-3-(1′-tert-butylamino-1′H, 3′ H-benzo[c]furan-3′-yl)-2-tert-butyl-2,3-dihydro-1H-benzo[c]pyrrol-1-one
- A new Z′=(2+0.5+0.5) amidophosphoester structure: Hirshfeld surface analysis of symmetry-independent molecules
- Crystal packing and layered morphology relationships in naphthalene sulfonate compounds
- Crystallographic aspects of hydrated salts of 4,6-diaminopyrimidine with the first five dicarboxylic acids
