[2-(Dimethyl­sulfonio)-1-hydr­oxy-1-phosphono­ethyl]phospho­nate monohydrate

In the title crystal structure, C₄H₁₂O₇P₂S·H₂O, the sulfonium groups have a pyramidal geometry and bridging water mol­ecules form a complex three-dimensional hydrogen-bond network involving neighboring phospho­nate groups.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.001 Å
• R factor = 0.024
• wR factor = 0.071
• Data-to-parameter ratio = 32.1

checkCIF/PLATON results

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: XCIF (Bruker, 2001).

[2-(Dimethylsulfonio)-1-hydroxy-1-phosphonoethyl]phosphonate monohydrate

Crystal data

C4H12O7P2S·H2O	F(000) = 592
Mr = 284.15	Dx = 1.756 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7336 reflections
a = 7.1107 (2) Å	θ = 2.9–36.3°
b = 10.2149 (3) Å	µ = 0.62 mm^−1
c = 15.1091 (4) Å	T = 273 K
β = 101.653 (10)°	Column, colourless
V = 1074.83 (6) Å^3	0.51 × 0.24 × 0.03 mm
Z = 4

Data collection

Bruker Kappa-APEXII CCD diffractometer	5196 independent reflections
Radiation source: fine-focus sealed tube	4605 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
profile data from φ and ω scans	θmax = 36.3°, θmin = 2.4°
Absorption correction: integration (SHELXTL/XPREP; Bruker, 2001)	h = −11→11
Tmin = 0.774, Tmax = 0.955	k = −15→17
26896 measured reflections	l = −13→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0343P)^2 + 0.3181P] where P = (Fo^2 + 2Fc^2)/3
5196 reflections	(Δ/σ)max = 0.002
162 parameters	Δρmax = 0.68 e Å^−3
8 restraints	Δρmin = −0.55 e Å^−3

Special details

Experimental. One distinct cell was identified using SMART (Bruker, 2001). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2001) then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001) before using SAINT/SADABS (Bruker, 2001) to sort, merge, and scale the combined data. A series of identical frames was collected twice during the experiment to monitor decay. No decay correction was applied.

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

Refinement. Structure was phased by direct methods. Systematic conditions suggested the unambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F². The highest peaks in the final difference Fourier map were in the vicinity of atoms O8 and C1; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude or resolution.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P2	0.70350 (3)	−0.02181 (2)	0.184030 (14)	0.01263 (5)
P1	1.11687 (3)	0.07908 (2)	0.257862 (14)	0.01363 (5)
S1	0.88103 (3)	0.16268 (2)	0.444383 (14)	0.01728 (5)
O3	1.08811 (10)	0.17139 (6)	0.17939 (4)	0.01824 (11)
O7	0.91288 (10)	−0.06711 (6)	0.35237 (4)	0.01677 (11)
H4	0.912 (2)	−0.1419 (12)	0.3316 (10)	0.025*
O2	1.23470 (10)	0.14093 (7)	0.34649 (5)	0.01977 (12)
H2	1.225 (2)	0.2192 (13)	0.3521 (10)	0.030*
O4	0.79874 (9)	−0.11594 (7)	0.12925 (4)	0.01781 (11)
O5	0.65156 (10)	0.10906 (7)	0.13266 (5)	0.02254 (13)
H3	0.5447 (19)	0.1248 (16)	0.1109 (11)	0.034*
C1	0.88321 (11)	0.03158 (7)	0.28402 (5)	0.01243 (12)
O6	0.53863 (9)	−0.08127 (7)	0.21842 (5)	0.02215 (13)
C2	0.79474 (12)	0.15086 (8)	0.32309 (5)	0.01538 (13)
H5	0.8313 (19)	0.2341 (12)	0.2988 (9)	0.018*
H6	0.6609 (16)	0.1474 (13)	0.3151 (9)	0.018*
O1	1.21452 (10)	−0.05179 (7)	0.24599 (6)	0.02340 (14)
H1	1.3263 (19)	−0.0506 (16)	0.2410 (11)	0.035*
C4	0.69581 (15)	0.08011 (12)	0.48719 (7)	0.0293 (2)
H10	0.7157	0.0932	0.5527	0.044*
H11	0.6999	−0.0137	0.4741	0.044*
H12	0.5704	0.1156	0.4582	0.044*
C3	0.82372 (15)	0.33028 (10)	0.46176 (7)	0.02503 (18)
H7	0.6884	0.3464	0.4348	0.038*
H8	0.9049	0.3874	0.4333	0.038*
H9	0.8465	0.3487	0.5267	0.038*
O8	0.31972 (12)	0.17391 (11)	0.05454 (5)	0.03362 (19)
H14	0.267 (3)	0.1437 (18)	0.0016 (11)	0.050*
H13	0.237 (2)	0.1721 (18)	0.0888 (12)	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P2	0.01025 (8)	0.01429 (9)	0.01330 (8)	0.00040 (6)	0.00227 (6)	0.00036 (6)
P1	0.01188 (8)	0.01169 (9)	0.01732 (9)	−0.00087 (6)	0.00297 (6)	0.00015 (6)
S1	0.01410 (8)	0.02480 (10)	0.01296 (8)	0.00232 (7)	0.00278 (6)	0.00028 (7)
O3	0.0213 (3)	0.0175 (3)	0.0169 (3)	−0.0027 (2)	0.0061 (2)	0.0010 (2)
O7	0.0220 (3)	0.0127 (2)	0.0149 (2)	0.0012 (2)	0.0021 (2)	0.00326 (19)
O2	0.0195 (3)	0.0168 (3)	0.0201 (3)	−0.0035 (2)	−0.0028 (2)	0.0013 (2)
O4	0.0182 (3)	0.0199 (3)	0.0160 (3)	0.0010 (2)	0.0049 (2)	−0.0033 (2)
O5	0.0195 (3)	0.0221 (3)	0.0237 (3)	0.0039 (2)	−0.0011 (2)	0.0078 (2)
C1	0.0124 (3)	0.0117 (3)	0.0131 (3)	0.0011 (2)	0.0023 (2)	0.0012 (2)
O6	0.0129 (3)	0.0266 (3)	0.0287 (3)	−0.0032 (2)	0.0081 (2)	−0.0004 (3)
C2	0.0179 (3)	0.0154 (3)	0.0125 (3)	0.0039 (3)	0.0023 (2)	−0.0001 (2)
O1	0.0143 (3)	0.0150 (3)	0.0423 (4)	0.0011 (2)	0.0090 (3)	−0.0037 (3)
C4	0.0221 (4)	0.0417 (6)	0.0255 (4)	0.0015 (4)	0.0084 (3)	0.0137 (4)
C3	0.0270 (4)	0.0287 (5)	0.0200 (4)	0.0027 (4)	0.0060 (3)	−0.0081 (3)
O8	0.0211 (3)	0.0601 (6)	0.0191 (3)	0.0112 (4)	0.0028 (3)	0.0045 (3)

Geometric parameters (Å, º)

P2—O6	1.5031 (7)	O5—H3	0.781 (13)
P2—O4	1.5148 (7)	C1—C2	1.5423 (11)
P2—O5	1.5525 (7)	C2—H5	0.982 (11)
P2—C1	1.8528 (8)	C2—H6	0.935 (11)
P1—O3	1.4962 (7)	O1—H1	0.814 (13)
P1—O1	1.5335 (7)	C4—H10	0.9800
P1—O2	1.5624 (7)	C4—H11	0.9800
P1—C1	1.8486 (8)	C4—H12	0.9800
S1—C4	1.7912 (10)	C3—H7	0.9800
S1—C3	1.7914 (11)	C3—H8	0.9800
S1—C2	1.8153 (8)	C3—H9	0.9800
O7—C1	1.4281 (10)	O8—H14	0.867 (14)
O7—H4	0.826 (12)	O8—H13	0.859 (14)
O2—H2	0.809 (13)
O6—P2—O4	113.48 (4)	C2—C1—P2	106.09 (5)
O6—P2—O5	113.41 (4)	P1—C1—P2	113.87 (4)
O4—P2—O5	111.15 (4)	C1—C2—S1	110.98 (5)
O6—P2—C1	107.14 (4)	C1—C2—H5	112.5 (8)
O4—P2—C1	108.76 (4)	S1—C2—H5	105.0 (8)
O5—P2—C1	102.09 (4)	C1—C2—H6	113.8 (8)
O3—P1—O1	116.70 (4)	S1—C2—H6	105.1 (8)
O3—P1—O2	112.84 (4)	H5—C2—H6	108.9 (11)
O1—P1—O2	106.00 (4)	P1—O1—H1	118.2 (12)
O3—P1—C1	110.48 (4)	S1—C4—H10	109.5
O1—P1—C1	104.12 (4)	S1—C4—H11	109.5
O2—P1—C1	105.81 (4)	H10—C4—H11	109.5
C4—S1—C3	101.04 (5)	S1—C4—H12	109.5
C4—S1—C2	102.12 (5)	H10—C4—H12	109.5
C3—S1—C2	99.85 (4)	H11—C4—H12	109.5
C1—O7—H4	112.9 (10)	S1—C3—H7	109.5
P1—O2—H2	116.6 (11)	S1—C3—H8	109.5
P2—O5—H3	120.0 (12)	H7—C3—H8	109.5
O7—C1—C2	107.04 (6)	S1—C3—H9	109.5
O7—C1—P1	109.39 (5)	H7—C3—H9	109.5
C2—C1—P1	109.16 (5)	H8—C3—H9	109.5
O7—C1—P2	111.02 (5)	H14—O8—H13	109.2 (18)
O3—P1—C1—O7	173.72 (5)	O6—P2—C1—C2	−70.82 (6)
O1—P1—C1—O7	47.67 (6)	O4—P2—C1—C2	166.15 (5)
O2—P1—C1—O7	−63.84 (6)	O5—P2—C1—C2	48.61 (6)
O3—P1—C1—C2	−69.47 (6)	O6—P2—C1—P1	169.11 (4)
O1—P1—C1—C2	164.48 (5)	O4—P2—C1—P1	46.08 (5)
O2—P1—C1—C2	52.98 (6)	O5—P2—C1—P1	−71.46 (5)
O3—P1—C1—P2	48.86 (5)	O7—C1—C2—S1	31.82 (8)
O1—P1—C1—P2	−77.19 (5)	P1—C1—C2—S1	−86.48 (6)
O2—P1—C1—P2	171.31 (4)	P2—C1—C2—S1	150.43 (4)
O6—P2—C1—O7	45.13 (6)	C4—S1—C2—C1	−94.87 (7)
O4—P2—C1—O7	−77.90 (6)	C3—S1—C2—C1	161.48 (6)
O5—P2—C1—O7	164.55 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H13···O3^i	0.86 (1)	1.89 (2)	2.7435 (11)	171 (2)
O7—H4···O3^ii	0.83 (1)	1.92 (1)	2.7138 (9)	163 (1)
O2—H2···O4^iii	0.81 (1)	1.72 (1)	2.5287 (10)	176 (2)
O1—H1···O6^iv	0.81 (1)	1.64 (1)	2.4420 (9)	166 (2)
O5—H3···O8	0.78 (1)	1.73 (1)	2.5049 (10)	173 (2)
O8—H14···O4^v	0.87 (1)	1.96 (2)	2.7975 (11)	162 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2; (iv) x+1, y, z; (v) −x+1, −y, −z.