Acta Crystallographica Section B

Structural Science, Crystal Engineering and Materials

Volume 69, Part 3 (June 2013)

research papers

Acta Cryst. (2013). B69, 260-270    [ doi:10.1107/S2052519213009445 ]

Hirshfeld surface analysis of new phosphoramidates

A. Tarahhomi, M. Pourayoubi, J. A. Golen, P. Zargaran, B. Elahi, A. L. Rheingold, M. A. Leyva Ramírez and T. Mancilla Percino

Abstract: Hirshfeld surfaces and two-dimensional fingerprint plots are used to visualize and analyze intermolecular interactions in six new phosphoramidate structures, [2,6-F2-C6H3C(O)NH]P(O)[X]2 {X = N(C2H5)2 (1), [X]2 = NHCH2C(CH3)2CH2NH and with one CH3OH solvated molecule (2)}, [C6H5O]2P(O)Y [Y = NC4H8O (3), NHC6H4(3-Br) (4)] and [Z]2P(O)OP(O)[Z]2 [Z = N(CH3)(CH2C6H5) (5), NHC6H4(4-CH3) (6)]. Study of the short intermolecular contacts in structures (1)-(6) by Hirshfeld surfaces demonstrate that the O atom of P=O is a better H-atom acceptor than the O atom of C=O for (1) and (2), and also relative to the O atom of the C6H5O group for (3) and (4), and relative to the bridge O atom of the P(O)OP(O) segment for (5) and (6). The results confirm that the crystal packing is related to the kind of substituent linked to the P atom. Compounds (1), (2), (4) and (6), with characteristic N-H...O hydrogen bonds, show a pair of intense spikes (including the intermolecular H...O contacts) in the fingerprint plots, summarizing the major features of each structure in the related two-dimensional plot. For (3) and (5), without any N-H unit, the two short spikes are observed for (3) but are absent for (5). The upper de and di values (distances to the Hirshfeld surfaces for the nearest atoms outside and inside) in the fingerprint plots are more compact in (3) than in (4), and in (5) than in (6), reflecting the more efficient packing in (3) and (5). The tertiary N atoms of (3) and (5) do not take part in any intermolecular contacts involving H atoms. Moreover, structures (3)-(6) show greater contribution from C...H contacts relative to O...H contacts. Finally, Hirshfeld surfaces and fingerprint plots are employed for a comparison of the two independent molecules in the asymmetric unit of (1) and also, for a comparison of (6), in the orthorhombic crystal system, with the previously reported monoclinic polymorph (Pourayoubi, Fadaei et al., 2012).

Keywords: Hirshfeld surface analysis; two-dimensional fingerprint plots; hydrogen bonding.

hkldisplay filedownload file

Structure factor file (CIF format) (383.8 kbytes)
[ doi:10.1107/S2052519213009445/so5063Isup2.hkl ]
Contains datablock I

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Structure factor file (CIF format) (128.0 kbytes)
[ doi:10.1107/S2052519213009445/so5063IIsup3.hkl ]
Contains datablock atar17

hkldisplay filedownload file

Structure factor file (CIF format) (153.5 kbytes)
[ doi:10.1107/S2052519213009445/so5063IIIsup4.hkl ]
Contains datablock tm16

hkldisplay filedownload file

Structure factor file (CIF format) (193.0 kbytes)
[ doi:10.1107/S2052519213009445/so5063IVsup5.hkl ]
Contains datablock tm18

hkldisplay filedownload file

Structure factor file (CIF format) (130.8 kbytes)
[ doi:10.1107/S2052519213009445/so5063Vsup6.hkl ]
Contains datablock V

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Structure factor file (CIF format) (148.4 kbytes)
[ doi:10.1107/S2052519213009445/so5063VIsup7.hkl ]
Contains datablock atar29


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