Tetra-methyl-ammonium dimethyl (phenyl-sulfonyl-amido)phosphate(1-).

The title compound, C(4)H(12)N(+)·C(8)H(11)NO(5)PS(-), was obtained from tetra-methyl-ammonium hydroxide and dimeth-yl(phenyl-sulfon-yl)amido-phosphate. The tetra-methyl-ammonium cation has a slightly distorted tetra-hedral 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.

Related literature

For the synthesis of sulfonyl­amide derivatives, see: Kirsanov & Shevchenko (1956 ▶); Pietraszkiewicz et al. (2002 ▶); Trush et al. (2009 ▶); Moroz et al. (2009 ▶); Shatrava et al. (2010 ▶). For the crystal structures of tetra­methyl­ammonium compounds, see: Cao et al. (2008 ▶); Liu et al. (2004 ▶).

Experimental

Crystal data

C4H12N+·C8H11NO5PS−

M = 338.36

Monoclinic,

a = 15.2840 (9) Å

b = 9.269 (2) Å

c = 12.1650 (11) Å

β = 98.279 (9)°

V = 1705.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 293 K

0.40 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.582, T max = 1.000

8644 measured reflections

3928 independent reflections

2406 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.063

S = 0.77

3928 reflections

197 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 1444 Friedel pairs

Flack parameter: 0.05 (6)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP within SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055024/wn2457sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055024/wn2457Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H12N+·C8H11NO5PS−	F(000) = 720
Mr = 338.36	Dx = 1.318 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 15.2840 (9) Å	Cell parameters from 2883 reflections
b = 9.269 (2) Å	θ = 3.0–32.2°
c = 12.1650 (11) Å	µ = 0.30 mm−1
β = 98.279 (9)°	T = 293 K
V = 1705.4 (4) Å3	Needle, colourless
Z = 4	0.40 × 0.20 × 0.10 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3928 independent reflections
Radiation source: fine-focus sealed tube	2406 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 16.1827 pixels mm-1	θmax = 30.0°, θmin = 3.0°
ω scans	h = −21→20
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→13
Tmin = 0.582, Tmax = 1.000	l = −17→17
8644 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0302P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.063	(Δ/σ)max < 0.001
S = 0.77	Δρmax = 0.23 e Å−3
3928 reflections	Δρmin = −0.15 e Å−3
197 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.0053 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1444 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.05 (6)

Experimental. Analysis found: IR (KBr pellet, cm-1): 1245(ν), 1220(νs), 1190(νs), 1060(νs), 1040(δ); 1060 (s, SO2) and 1190 (s, PO). 1H NMR (DMSO-d6): 3.4 d 6H, 3JPH =11.6 Hz; 7.78 dd (α), 2H; 7.38 m (β+γ), 3H; 31P (DMSO-d6) -3.27 h, 3JHP = 11.6 Hz.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
P1	−0.72846 (3)	−0.17887 (6)	−0.99705 (4)	0.03893 (14)
S1	−0.88898 (4)	−0.24929 (6)	−0.92536 (5)	0.04416 (14)
N1	−0.83352 (11)	−0.18063 (19)	−1.00894 (14)	0.0476 (4)
N2	−0.57619 (11)	−0.5029 (2)	−0.71028 (15)	0.0466 (5)
O1	−0.86516 (14)	−0.20683 (19)	−0.81208 (13)	0.0773 (6)
O2	−0.98092 (11)	−0.22632 (19)	−0.96904 (16)	0.0740 (5)
O3	−0.67793 (12)	−0.30800 (18)	−0.96015 (16)	0.0681 (5)
O4	−0.69770 (10)	−0.04211 (17)	−0.92503 (14)	0.0618 (4)
O5	−0.70883 (10)	−0.14025 (18)	−1.11691 (12)	0.0586 (4)
C1	−0.87219 (12)	−0.4386 (2)	−0.92758 (17)	0.0373 (5)
C2	−0.86269 (19)	−0.5079 (3)	−1.0247 (2)	0.0609 (6)
H2	−0.8643	−0.4558	−1.0902	0.073*
C3	−0.8507 (2)	−0.6556 (3)	−1.0247 (2)	0.0725 (8)
H3	−0.8449	−0.7025	−1.0908	0.087*
C4	−0.84735 (16)	−0.7336 (3)	−0.9293 (2)	0.0635 (7)
H4	−0.8390	−0.8329	−0.9298	0.076*
C5	−0.85644 (15)	−0.6633 (3)	−0.8328 (2)	0.0567 (6)
H5	−0.8545	−0.7152	−0.7671	0.068*
C6	−0.86836 (14)	−0.5174 (3)	−0.83254 (17)	0.0474 (6)
H6	−0.8740	−0.4709	−0.7662	0.057*
C7	−0.60472 (19)	−0.0089 (4)	−0.9058 (3)	0.1007 (12)
H7A	−0.5927	0.0693	−0.9531	0.151*
H7B	−0.5715	−0.0923	−0.9218	0.151*
H7C	−0.5880	0.0184	−0.8295	0.151*
C8	−0.7451 (2)	−0.0104 (3)	−1.1696 (2)	0.0815 (9)
H8B	−0.7178	0.0719	−1.1307	0.122*
H8A	−0.8077	−0.0078	−1.1680	0.122*
H8C	−0.7339	−0.0084	−1.2453	0.122*
C9	−0.62334 (17)	−0.5989 (3)	−0.7979 (2)	0.0644 (7)
H9B	−0.6614	−0.6634	−0.7650	0.097*
H9A	−0.5809	−0.6538	−0.8314	0.097*
H9C	−0.6581	−0.5414	−0.8535	0.097*
C10	−0.52163 (19)	−0.5918 (3)	−0.6247 (2)	0.0697 (7)
H10B	−0.4877	−0.5297	−0.5716	0.105*
H10A	−0.4824	−0.6516	−0.6597	0.105*
H10C	−0.5595	−0.6515	−0.5876	0.105*
C11	−0.51646 (17)	−0.4051 (3)	−0.7616 (2)	0.0689 (7)
H11C	−0.4744	−0.4614	−0.7947	0.103*
H11B	−0.4857	−0.3433	−0.7056	0.103*
H11A	−0.5507	−0.3475	−0.8177	0.103*
C12	−0.63993 (19)	−0.4189 (3)	−0.6587 (2)	0.0727 (8)
H12C	−0.6751	−0.3617	−0.7142	0.109*
H12B	−0.6091	−0.3567	−0.6030	0.109*
H12A	−0.6776	−0.4830	−0.6249	0.109*

	U11	U22	U33	U12	U13	U23
P1	0.0396 (3)	0.0345 (3)	0.0437 (3)	−0.0002 (3)	0.0096 (2)	0.0012 (3)
S1	0.0473 (3)	0.0415 (3)	0.0467 (3)	−0.0013 (2)	0.0171 (2)	0.0014 (3)
N1	0.0389 (10)	0.0518 (11)	0.0528 (11)	−0.0007 (8)	0.0085 (8)	0.0104 (9)
N2	0.0414 (11)	0.0503 (12)	0.0489 (11)	−0.0025 (9)	0.0087 (8)	0.0038 (9)
O1	0.1328 (17)	0.0603 (11)	0.0427 (10)	−0.0138 (11)	0.0264 (10)	−0.0104 (8)
O2	0.0463 (10)	0.0711 (11)	0.1084 (15)	0.0072 (8)	0.0238 (9)	0.0168 (10)
O3	0.0553 (11)	0.0492 (10)	0.0971 (14)	0.0065 (8)	0.0017 (9)	0.0155 (9)
O4	0.0595 (11)	0.0609 (11)	0.0665 (11)	−0.0170 (8)	0.0142 (8)	−0.0184 (9)
O5	0.0662 (11)	0.0632 (11)	0.0513 (10)	0.0048 (8)	0.0248 (8)	0.0029 (8)
C1	0.0332 (11)	0.0441 (11)	0.0348 (11)	−0.0091 (8)	0.0064 (8)	−0.0025 (10)
C2	0.0954 (19)	0.0482 (14)	0.0417 (13)	−0.0123 (13)	0.0188 (12)	−0.0044 (11)
C3	0.101 (2)	0.0536 (17)	0.0659 (18)	−0.0144 (14)	0.0224 (15)	−0.0256 (14)
C4	0.0629 (16)	0.0392 (14)	0.089 (2)	−0.0055 (11)	0.0140 (14)	−0.0010 (15)
C5	0.0580 (16)	0.0503 (15)	0.0607 (16)	−0.0055 (11)	0.0047 (12)	0.0146 (12)
C6	0.0552 (14)	0.0525 (14)	0.0344 (13)	−0.0052 (11)	0.0059 (10)	0.0045 (10)
C7	0.073 (2)	0.102 (3)	0.124 (3)	−0.0374 (19)	0.0050 (19)	−0.027 (2)
C8	0.101 (2)	0.081 (2)	0.0664 (18)	0.0027 (17)	0.0261 (16)	0.0275 (15)
C9	0.0523 (15)	0.0679 (16)	0.0732 (17)	−0.0069 (12)	0.0099 (13)	−0.0097 (14)
C10	0.0601 (15)	0.0793 (18)	0.0679 (18)	0.0110 (14)	0.0030 (12)	0.0266 (14)
C11	0.0565 (16)	0.0727 (18)	0.0772 (19)	−0.0160 (13)	0.0083 (13)	0.0213 (14)
C12	0.0573 (15)	0.0800 (19)	0.081 (2)	0.0114 (15)	0.0116 (13)	−0.0142 (16)

P1—O3	1.4597 (17)	C5—C6	1.365 (3)
P1—O5	1.5718 (16)	C5—H5	0.9300
P1—O4	1.5738 (16)	C6—H6	0.9300
P1—N1	1.5915 (17)	C7—H7A	0.9600
S1—O1	1.4290 (16)	C7—H7B	0.9600
S1—O2	1.4447 (16)	C7—H7C	0.9600
S1—N1	1.5510 (18)	C8—H8B	0.9600
S1—C1	1.774 (2)	C8—H8A	0.9600
N2—C12	1.457 (3)	C8—H8C	0.9600
N2—C10	1.486 (3)	C9—H9B	0.9600
N2—C11	1.486 (3)	C9—H9A	0.9600
N2—C9	1.492 (3)	C9—H9C	0.9600
O4—C7	1.440 (3)	C10—H10B	0.9600
O5—C8	1.437 (3)	C10—H10A	0.9600
C1—C6	1.362 (3)	C10—H10C	0.9600
C1—C2	1.370 (3)	C11—H11C	0.9600
C2—C3	1.381 (4)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.361 (4)	C12—H12C	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.367 (3)	C12—H12A	0.9600
C4—H4	0.9300
O3—P1—O5	107.99 (10)	C5—C6—H6	119.4
O3—P1—O4	112.76 (10)	O4—C7—H7A	109.5
O5—P1—O4	104.56 (9)	O4—C7—H7B	109.5
O3—P1—N1	120.12 (10)	H7A—C7—H7B	109.5
O5—P1—N1	104.05 (9)	O4—C7—H7C	109.5
O4—P1—N1	105.99 (9)	H7A—C7—H7C	109.5
O1—S1—O2	114.42 (12)	H7B—C7—H7C	109.5
O1—S1—N1	115.58 (11)	O5—C8—H8B	109.5
O2—S1—N1	107.03 (10)	O5—C8—H8A	109.5
O1—S1—C1	105.65 (11)	H8B—C8—H8A	109.5
O2—S1—C1	105.98 (10)	O5—C8—H8C	109.5
N1—S1—C1	107.57 (10)	H8B—C8—H8C	109.5
S1—N1—P1	125.74 (11)	H8A—C8—H8C	109.5
C12—N2—C10	109.7 (2)	N2—C9—H9B	109.5
C12—N2—C11	110.1 (2)	N2—C9—H9A	109.5
C10—N2—C11	108.40 (18)	H9B—C9—H9A	109.5
C12—N2—C9	109.99 (19)	N2—C9—H9C	109.5
C10—N2—C9	109.5 (2)	H9B—C9—H9C	109.5
C11—N2—C9	109.07 (19)	H9A—C9—H9C	109.5
C7—O4—P1	118.14 (16)	N2—C10—H10B	109.5
C8—O5—P1	119.47 (16)	N2—C10—H10A	109.5
C6—C1—C2	118.9 (2)	H10B—C10—H10A	109.5
C6—C1—S1	120.41 (16)	N2—C10—H10C	109.5
C2—C1—S1	120.68 (17)	H10B—C10—H10C	109.5
C1—C2—C3	119.7 (2)	H10A—C10—H10C	109.5
C1—C2—H2	120.2	N2—C11—H11C	109.5
C3—C2—H2	120.2	N2—C11—H11B	109.5
C4—C3—C2	121.0 (2)	H11C—C11—H11B	109.5
C4—C3—H3	119.5	N2—C11—H11A	109.5
C2—C3—H3	119.5	H11C—C11—H11A	109.5
C3—C4—C5	118.9 (2)	H11B—C11—H11A	109.5
C3—C4—H4	120.6	N2—C12—H12C	109.5
C5—C4—H4	120.6	N2—C12—H12B	109.5
C6—C5—C4	120.3 (2)	H12C—C12—H12B	109.5
C6—C5—H5	119.9	N2—C12—H12A	109.5
C4—C5—H5	119.9	H12C—C12—H12A	109.5
C1—C6—C5	121.2 (2)	H12B—C12—H12A	109.5
C1—C6—H6	119.4