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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004405/lh6585sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004405/lh6585Isup2.hkl
Contains datablock I

CCDC reference: 601210

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

No syntax errors found


No errors found in this datablock

Computing details top

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 top
Crystal data top
C4H12O7P2S·H2OF(000) = 592
Mr = 284.15Dx = 1.756 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7336 reflections
a = 7.1107 (2) Åθ = 2.9–36.3°
b = 10.2149 (3) ŵ = 0.62 mm1
c = 15.1091 (4) ÅT = 273 K
β = 101.653 (10)°Column, colourless
V = 1074.83 (6) Å30.51 × 0.24 × 0.03 mm
Z = 4
Data collection top
Bruker Kappa-APEXII CCD
diffractometer
5196 independent reflections
Radiation source: fine-focus sealed tube4605 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
profile data from φ and ω scansθmax = 36.3°, θmin = 2.4°
Absorption correction: integration
(SHELXTL/XPREP; Bruker, 2001)
h = 1111
Tmin = 0.774, Tmax = 0.955k = 1517
26896 measured reflectionsl = 1325
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0343P)2 + 0.3181P]
where P = (Fo2 + 2Fc2)/3
5196 reflections(Δ/σ)max = 0.002
162 parametersΔρmax = 0.68 e Å3
8 restraintsΔρmin = 0.55 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
P20.70350 (3)0.02181 (2)0.184030 (14)0.01263 (5)
P11.11687 (3)0.07908 (2)0.257862 (14)0.01363 (5)
S10.88103 (3)0.16268 (2)0.444383 (14)0.01728 (5)
O31.08811 (10)0.17139 (6)0.17939 (4)0.01824 (11)
O70.91288 (10)0.06711 (6)0.35237 (4)0.01677 (11)
H40.912 (2)0.1419 (12)0.3316 (10)0.025*
O21.23470 (10)0.14093 (7)0.34649 (5)0.01977 (12)
H21.225 (2)0.2192 (13)0.3521 (10)0.030*
O40.79874 (9)0.11594 (7)0.12925 (4)0.01781 (11)
O50.65156 (10)0.10906 (7)0.13266 (5)0.02254 (13)
H30.5447 (19)0.1248 (16)0.1109 (11)0.034*
C10.88321 (11)0.03158 (7)0.28402 (5)0.01243 (12)
O60.53863 (9)0.08127 (7)0.21842 (5)0.02215 (13)
C20.79474 (12)0.15086 (8)0.32309 (5)0.01538 (13)
H50.8313 (19)0.2341 (12)0.2988 (9)0.018*
H60.6609 (16)0.1474 (13)0.3151 (9)0.018*
O11.21452 (10)0.05179 (7)0.24599 (6)0.02340 (14)
H11.3263 (19)0.0506 (16)0.2410 (11)0.035*
C40.69581 (15)0.08011 (12)0.48719 (7)0.0293 (2)
H100.71570.09320.55270.044*
H110.69990.01370.47410.044*
H120.57040.11560.45820.044*
C30.82372 (15)0.33028 (10)0.46176 (7)0.02503 (18)
H70.68840.34640.43480.038*
H80.90490.38740.43330.038*
H90.84650.34870.52670.038*
O80.31972 (12)0.17391 (11)0.05454 (5)0.03362 (19)
H140.267 (3)0.1437 (18)0.0016 (11)0.050*
H130.237 (2)0.1721 (18)0.0888 (12)0.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P20.01025 (8)0.01429 (9)0.01330 (8)0.00040 (6)0.00227 (6)0.00036 (6)
P10.01188 (8)0.01169 (9)0.01732 (9)0.00087 (6)0.00297 (6)0.00015 (6)
S10.01410 (8)0.02480 (10)0.01296 (8)0.00232 (7)0.00278 (6)0.00028 (7)
O30.0213 (3)0.0175 (3)0.0169 (3)0.0027 (2)0.0061 (2)0.0010 (2)
O70.0220 (3)0.0127 (2)0.0149 (2)0.0012 (2)0.0021 (2)0.00326 (19)
O20.0195 (3)0.0168 (3)0.0201 (3)0.0035 (2)0.0028 (2)0.0013 (2)
O40.0182 (3)0.0199 (3)0.0160 (3)0.0010 (2)0.0049 (2)0.0033 (2)
O50.0195 (3)0.0221 (3)0.0237 (3)0.0039 (2)0.0011 (2)0.0078 (2)
C10.0124 (3)0.0117 (3)0.0131 (3)0.0011 (2)0.0023 (2)0.0012 (2)
O60.0129 (3)0.0266 (3)0.0287 (3)0.0032 (2)0.0081 (2)0.0004 (3)
C20.0179 (3)0.0154 (3)0.0125 (3)0.0039 (3)0.0023 (2)0.0001 (2)
O10.0143 (3)0.0150 (3)0.0423 (4)0.0011 (2)0.0090 (3)0.0037 (3)
C40.0221 (4)0.0417 (6)0.0255 (4)0.0015 (4)0.0084 (3)0.0137 (4)
C30.0270 (4)0.0287 (5)0.0200 (4)0.0027 (4)0.0060 (3)0.0081 (3)
O80.0211 (3)0.0601 (6)0.0191 (3)0.0112 (4)0.0028 (3)0.0045 (3)
Geometric parameters (Å, º) top
P2—O61.5031 (7)O5—H30.781 (13)
P2—O41.5148 (7)C1—C21.5423 (11)
P2—O51.5525 (7)C2—H50.982 (11)
P2—C11.8528 (8)C2—H60.935 (11)
P1—O31.4962 (7)O1—H10.814 (13)
P1—O11.5335 (7)C4—H100.9800
P1—O21.5624 (7)C4—H110.9800
P1—C11.8486 (8)C4—H120.9800
S1—C41.7912 (10)C3—H70.9800
S1—C31.7914 (11)C3—H80.9800
S1—C21.8153 (8)C3—H90.9800
O7—C11.4281 (10)O8—H140.867 (14)
O7—H40.826 (12)O8—H130.859 (14)
O2—H20.809 (13)
O6—P2—O4113.48 (4)C2—C1—P2106.09 (5)
O6—P2—O5113.41 (4)P1—C1—P2113.87 (4)
O4—P2—O5111.15 (4)C1—C2—S1110.98 (5)
O6—P2—C1107.14 (4)C1—C2—H5112.5 (8)
O4—P2—C1108.76 (4)S1—C2—H5105.0 (8)
O5—P2—C1102.09 (4)C1—C2—H6113.8 (8)
O3—P1—O1116.70 (4)S1—C2—H6105.1 (8)
O3—P1—O2112.84 (4)H5—C2—H6108.9 (11)
O1—P1—O2106.00 (4)P1—O1—H1118.2 (12)
O3—P1—C1110.48 (4)S1—C4—H10109.5
O1—P1—C1104.12 (4)S1—C4—H11109.5
O2—P1—C1105.81 (4)H10—C4—H11109.5
C4—S1—C3101.04 (5)S1—C4—H12109.5
C4—S1—C2102.12 (5)H10—C4—H12109.5
C3—S1—C299.85 (4)H11—C4—H12109.5
C1—O7—H4112.9 (10)S1—C3—H7109.5
P1—O2—H2116.6 (11)S1—C3—H8109.5
P2—O5—H3120.0 (12)H7—C3—H8109.5
O7—C1—C2107.04 (6)S1—C3—H9109.5
O7—C1—P1109.39 (5)H7—C3—H9109.5
C2—C1—P1109.16 (5)H8—C3—H9109.5
O7—C1—P2111.02 (5)H14—O8—H13109.2 (18)
O3—P1—C1—O7173.72 (5)O6—P2—C1—C270.82 (6)
O1—P1—C1—O747.67 (6)O4—P2—C1—C2166.15 (5)
O2—P1—C1—O763.84 (6)O5—P2—C1—C248.61 (6)
O3—P1—C1—C269.47 (6)O6—P2—C1—P1169.11 (4)
O1—P1—C1—C2164.48 (5)O4—P2—C1—P146.08 (5)
O2—P1—C1—C252.98 (6)O5—P2—C1—P171.46 (5)
O3—P1—C1—P248.86 (5)O7—C1—C2—S131.82 (8)
O1—P1—C1—P277.19 (5)P1—C1—C2—S186.48 (6)
O2—P1—C1—P2171.31 (4)P2—C1—C2—S1150.43 (4)
O6—P2—C1—O745.13 (6)C4—S1—C2—C194.87 (7)
O4—P2—C1—O777.90 (6)C3—S1—C2—C1161.48 (6)
O5—P2—C1—O7164.55 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H13···O3i0.86 (1)1.89 (2)2.7435 (11)171 (2)
O7—H4···O3ii0.83 (1)1.92 (1)2.7138 (9)163 (1)
O2—H2···O4iii0.81 (1)1.72 (1)2.5287 (10)176 (2)
O1—H1···O6iv0.81 (1)1.64 (1)2.4420 (9)166 (2)
O5—H3···O80.78 (1)1.73 (1)2.5049 (10)173 (2)
O8—H14···O4v0.87 (1)1.96 (2)2.7975 (11)162 (2)
Symmetry codes: (i) x1, y, z; (ii) x+2, y1/2, z+1/2; (iii) x+2, y+1/2, z+1/2; (iv) x+1, y, z; (v) x+1, y, z.
 

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