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 d(e) and d(i) 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).
The asymmetric unit of the title compound, C23H28N3OP, contains two independent molecules with significant conformational differences. For example, the torsion angles N—C—C—C involving the N-benzyl moieties are 57.3 (7) and 11.6 (8)° in one molecule and 76.5 (7) and 97.4 (7)° in the other. In each molecule, the P atom exhibits a distorted tetrahedral conformation [the bond angles at P are in the ranges 104.7 (2)–115.2 (2) and 105.1 (2)–115.1 (2)° in the two molecules], and the phosphoryl group and the N—H group adopt an anti orientation with respect to one another. In the crystal, molecules are linked via N—H⋯O(P) hydrogen bonds, forming a chain parallel to the a axis.
The P atom in the title molecule, C10H23ClN3O2P, has a distorted tetrahedral coordination. In the C(O)NHP(O) unit, which has syn-oriented phosphoryl and N—H groups, the P—N bond of 1.703 (2) Å is longer and the O—P—N angle of 103.86 (7)° is contracted compared with the respective values in the two P(O)NHC(CH3)3 units [P—N = 1.632 (2) and 1.624 (2) Å; O—P—N = 116.80 (8) and 115.32 (8)°]. In the crystal, each molecule is hydrogen bonded to two adjacent molecules via N—H⋯O hydrogen bonds, forming a linear sequence of alternating R
2
2(8) and R
2
2(12)/R
2
1(6)-fused rings along [010]. The O atom of the carbonyl group acts as a double H-atom acceptor.
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