Tetramethylammonium dimethyl (phenylsulfonylamido)phosphate(1−)

The title compound, C4H12N+·C8H11NO5PS−, was obtained from tetramethylammonium hydroxide and dimethyl(phenylsulfonyl)amidophosphate. The tetramethylammonium cation has a slightly distorted tetrahedral configuration and the N—C bond lengths lie in the range 1.457 (3)–1.492 (3) Å. In the crystal, no classical hydrogen bonds are observed between the cation and the anion.

The title compound, C 4 H 12 N + ÁC 8 H 11 NO 5 PS À , was obtained from tetramethylammonium hydroxide and dimethyl(phenylsulfonyl)amidophosphate. The tetramethylammonium cation has a slightly distorted tetrahedral configuration and the N-C bond lengths lie in the range 1.457 (3)-1.492 (3) Å . In the crystal, no classical hydrogen bonds are observed between the cation and the anion.   et al., 2002). Earlier sulfonylamide derivatives of the general type RSO 2 NHP(O)(R') 2 and their coordination compounds have been systematically investigated and some results of our study have been already published (Moroz et al., 2009, Shatrava et al., 2010, Trush et al. 2009). However, there are no reports of the crystal structure of any alkali-or onic-salts of dimethyl(phenylsulphonyl)amidophosphate (HL). This paper reports the crystal structure of the compound

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The highly polar anion contains six potential donor centers and, in spite of this fact, coordinated molecules of water or alcohol have not been detected. (Fig. 2).
The X-ray crystal structure reveals that there are no contacts shorter than 2.44 Å between cation and anion, (the presence of weak C-H···O contacts with the participation of PO and SO 2 oxygens and protons of cation is observed), so the bonding may be considered as mainly ionic.
The dimethyl(phenylsulfonyl)amidophosphatotetramethylammonium salt includes a deprotonated sulphonylamidophosphate anion and cation; the latter has a standard N(CH 3 ) 4 + -tetrahedral configuration (Fig. 1). The presence of non-equivalent values of C-N bond lengths is a general feature for earlier, structurally investigated tetramethylammonium compounds (Cao et al., 2008;Liu et al., 2004). The geometry of the nearest environment of the phosphorus atom in {L -} can be described as a distorted tetrahedron. The bond lengths P1-O3 and P1-N1 have values 1.460 (2) and 1.591 (2) Å, respectively, which are typical of phosphorylated sulfonylamide for compounds with ether-type substituents (Moroz et al., 2009).

Experimental
The dimethyl(phenylsulfonyl)amidophosphate (HL) was prepared according to the earlier published procedures (Kirsanov et al., 1956). The tetramethylammonium salt {N(CH 3 ) 4 + [C 6 H 5 SO 2 NP(O)(OCH 3 ) 2 ] -} was obtained by the neutralization reaction: tetramethylammonium hydroxide (0.365 g, 1 mmol of 25% solution) was added dropwise to an equimolar amount (0.265 g, 1 mmol) of HL which was dissolved in 10 ml of isopropanol. The completion of the reaction was checked with phenolphthalein. Colorless crystals suitable for X-ray diffraction were separated. The yield was 0.31 g (92% starting from HL).
supplementary materials sup-2 Refinement All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.93-0.96 Å and U iso (H) = xU eq (C), where x = 1.5 for methyl H and 1.2 for all other H atoms. A rotating-group model was applied for the methyl groups. The absolute configuration was determined and the Flack parameter refined to 0.05 (6). Fig. 1. The asymmetric unit of dimethyl(phenylsulfonyl)amidophosphato-tetramethylammonium. Displacement ellipsoids are drawn at the 20% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Special details
Experimental. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.