1-Hydr­oxy-1-phosphono-2-(trimethylarsonium-1-yl)ethanephospho­nate monohydrate

In the crystal structure of the title compound, C₅H₁₅AsO₇P₂·H₂O, hydrogen-bonded sheets are formed which contain bis­phospho­nate(1-) groups and water mol­ecules alternating with trimethyl­arsonium groups.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.092
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

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Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); 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).

1-Hydroxy-1-phosphono-2-(trimethylarsonium-1-yl)ethanephosphonate monohydrate

Crystal data

C5H15AsO7P2·H2O	F(000) = 696
Mr = 342.05	Dx = 1.808 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 897 reflections
a = 7.171 (8) Å	θ = 2.3–28.3°
b = 10.487 (12) Å	µ = 2.98 mm^−1
c = 16.849 (19) Å	T = 193 K
β = 97.284 (16)°	Tabular, colorless
V = 1257 (2) Å^3	0.32 × 0.17 × 0.05 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3126 independent reflections
Radiation source: normal-focus sealed tube	2265 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
profile data from ω scans	θmax = 28.4°, θmin = 2.3°
Absorption correction: integration (XPREP in SHELXTL; Bruker, 2001)	h = −9→9
Tmin = 0.442, Tmax = 0.865	k = −13→14
11918 measured reflections	l = −21→22

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0615P)^2] where P = (Fo^2 + 2Fc^2)/3
3126 reflections	(Δ/σ)max = 0.005
166 parameters	Δρmax = 0.56 e Å^−3
6 restraints	Δρmin = −0.76 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 un??ambiguous 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 O1, O2 and AS1; 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
As1	0.30346 (4)	0.24382 (3)	0.427167 (16)	0.02341 (11)
P1	0.61083 (10)	0.31476 (6)	0.24827 (4)	0.01909 (17)
P2	0.21705 (10)	0.42944 (6)	0.19458 (4)	0.01724 (16)
O4	0.1714 (3)	0.31903 (17)	0.13327 (11)	0.0231 (4)
H2	0.092 (4)	0.266 (3)	0.145 (2)	0.035*
O5	0.3122 (3)	0.53243 (16)	0.15290 (11)	0.0219 (4)
H3	0.286 (4)	0.6108 (19)	0.1618 (19)	0.033*
O7	0.4148 (3)	0.45757 (16)	0.34016 (11)	0.0202 (4)
H4	0.437 (4)	0.530 (2)	0.3250 (18)	0.030*
O1	0.7019 (3)	0.44102 (18)	0.22643 (14)	0.0288 (5)
H1	0.814 (3)	0.439 (3)	0.223 (2)	0.043*
O8	0.9309 (3)	0.14809 (19)	0.14542 (13)	0.0261 (5)
H17	0.945 (5)	0.097 (3)	0.1819 (16)	0.039*
H16	0.823 (3)	0.172 (3)	0.150 (2)	0.039*
O2	0.5835 (3)	0.21801 (17)	0.18300 (12)	0.0237 (4)
O3	0.7309 (3)	0.26290 (16)	0.32491 (12)	0.0242 (5)
O6	0.0477 (3)	0.46968 (18)	0.23345 (12)	0.0245 (4)
C4	0.2263 (6)	0.0752 (3)	0.44994 (19)	0.0409 (9)
H10	0.3147	0.0136	0.4319	0.061*
H11	0.1001	0.0594	0.4219	0.061*
H12	0.2244	0.0659	0.5077	0.061*
C1	0.3844 (4)	0.3643 (2)	0.27730 (15)	0.0162 (5)
C2	0.2922 (4)	0.2469 (2)	0.31254 (16)	0.0190 (6)
H5	0.3540	0.1690	0.2954	0.023*
H6	0.1585	0.2434	0.2891	0.023*
C5	0.1271 (5)	0.3619 (3)	0.45985 (19)	0.0395 (8)
H13	0.0040	0.3479	0.4286	0.059*
H14	0.1694	0.4491	0.4510	0.059*
H15	0.1170	0.3497	0.5168	0.059*
C3	0.5451 (5)	0.2703 (3)	0.4861 (2)	0.0403 (9)
H7	0.5346	0.2688	0.5435	0.061*
H8	0.5944	0.3531	0.4717	0.061*
H9	0.6306	0.2025	0.4734	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
As1	0.0333 (2)	0.02086 (15)	0.01615 (16)	−0.00157 (12)	0.00345 (12)	0.00139 (10)
P1	0.0181 (4)	0.0160 (3)	0.0232 (4)	0.0019 (3)	0.0029 (3)	0.0016 (3)
P2	0.0180 (4)	0.0160 (3)	0.0173 (3)	−0.0005 (3)	0.0007 (3)	−0.0006 (2)
O4	0.0287 (12)	0.0205 (9)	0.0201 (10)	−0.0063 (8)	0.0029 (9)	−0.0022 (7)
O5	0.0267 (11)	0.0155 (8)	0.0235 (10)	0.0002 (8)	0.0032 (8)	0.0008 (7)
O7	0.0267 (11)	0.0147 (8)	0.0186 (9)	−0.0038 (8)	0.0012 (8)	−0.0014 (7)
O1	0.0145 (11)	0.0219 (10)	0.0510 (14)	0.0011 (8)	0.0075 (10)	0.0106 (9)
O8	0.0230 (12)	0.0238 (10)	0.0326 (12)	−0.0013 (9)	0.0076 (10)	0.0023 (8)
O2	0.0277 (12)	0.0229 (9)	0.0208 (10)	0.0063 (8)	0.0045 (9)	−0.0020 (7)
O3	0.0225 (11)	0.0203 (9)	0.0278 (11)	0.0039 (8)	−0.0048 (9)	0.0022 (8)
O6	0.0185 (11)	0.0274 (10)	0.0274 (11)	0.0012 (8)	0.0023 (9)	−0.0023 (8)
C4	0.079 (3)	0.0229 (15)	0.0221 (15)	−0.0095 (16)	0.0106 (17)	0.0019 (12)
C1	0.0174 (14)	0.0147 (11)	0.0168 (12)	−0.0019 (10)	0.0030 (11)	−0.0015 (9)
C2	0.0219 (15)	0.0188 (12)	0.0164 (13)	−0.0025 (10)	0.0030 (11)	0.0006 (9)
C5	0.053 (2)	0.0381 (18)	0.0301 (18)	0.0092 (16)	0.0172 (17)	0.0009 (14)
C3	0.043 (2)	0.055 (2)	0.0206 (16)	−0.0042 (16)	−0.0066 (15)	0.0034 (14)

Geometric parameters (Å, º)

As1—C5	1.901 (4)	O1—H1	0.814 (18)
As1—C3	1.905 (4)	O8—H17	0.810 (18)
As1—C4	1.906 (3)	O8—H16	0.829 (18)
As1—C2	1.923 (3)	C4—H10	0.9800
P1—O2	1.491 (2)	C4—H11	0.9800
P1—O1	1.541 (2)	C4—H12	0.9800
P1—O3	1.556 (2)	C1—C2	1.551 (4)
P1—C1	1.830 (3)	C2—H5	0.9900
P2—O5	1.499 (2)	C2—H6	0.9900
P2—O6	1.511 (3)	C5—H13	0.9800
P2—O4	1.559 (2)	C5—H14	0.9800
P2—C1	1.851 (3)	C5—H15	0.9800
O4—H2	0.837 (18)	C3—H7	0.9800
O5—H3	0.861 (17)	C3—H8	0.9800
O7—C1	1.438 (3)	C3—H9	0.9800
O7—H4	0.827 (17)
C5—As1—C3	110.41 (17)	H10—C4—H12	109.5
C5—As1—C4	108.98 (17)	H11—C4—H12	109.5
C3—As1—C4	107.36 (16)	O7—C1—C2	106.9 (2)
C5—As1—C2	109.57 (13)	O7—C1—P1	109.48 (18)
C3—As1—C2	116.14 (15)	C2—C1—P1	108.23 (18)
C4—As1—C2	103.98 (12)	O7—C1—P2	109.10 (17)
O2—P1—O1	115.38 (14)	C2—C1—P2	108.30 (19)
O2—P1—O3	112.42 (13)	P1—C1—P2	114.60 (15)
O1—P1—O3	106.95 (12)	C1—C2—As1	115.61 (17)
O2—P1—C1	110.62 (12)	C1—C2—H5	108.4
O1—P1—C1	103.72 (13)	As1—C2—H5	108.4
O3—P1—C1	107.08 (13)	C1—C2—H6	108.4
O5—P2—O6	116.14 (13)	As1—C2—H6	108.4
O5—P2—O4	107.14 (13)	H5—C2—H6	107.4
O6—P2—O4	112.45 (12)	As1—C5—H13	109.5
O5—P2—C1	109.17 (13)	As1—C5—H14	109.5
O6—P2—C1	104.87 (14)	H13—C5—H14	109.5
O4—P2—C1	106.66 (12)	As1—C5—H15	109.5
P2—O4—H2	115 (3)	H13—C5—H15	109.5
P2—O5—H3	119 (2)	H14—C5—H15	109.5
C1—O7—H4	115 (2)	As1—C3—H7	109.5
P1—O1—H1	117 (3)	As1—C3—H8	109.5
H17—O8—H16	99 (4)	H7—C3—H8	109.5
As1—C4—H10	109.5	As1—C3—H9	109.5
As1—C4—H11	109.5	H7—C3—H9	109.5
H10—C4—H11	109.5	H8—C3—H9	109.5
As1—C4—H12	109.5
O2—P1—C1—O7	−179.95 (15)	O5—P2—C1—C2	−172.86 (16)
O1—P1—C1—O7	−55.7 (2)	O6—P2—C1—C2	62.1 (2)
O3—P1—C1—O7	57.23 (19)	O4—P2—C1—C2	−57.4 (2)
O2—P1—C1—C2	63.9 (2)	O5—P2—C1—P1	−51.94 (17)
O1—P1—C1—C2	−171.79 (17)	O6—P2—C1—P1	−177.03 (12)
O3—P1—C1—C2	−58.89 (19)	O4—P2—C1—P1	63.51 (16)
O2—P1—C1—P2	−57.02 (17)	O7—C1—C2—As1	−14.1 (3)
O1—P1—C1—P2	67.26 (16)	P1—C1—C2—As1	103.68 (18)
O3—P1—C1—P2	−179.84 (12)	P2—C1—C2—As1	−131.53 (16)
O5—P2—C1—O7	71.2 (2)	C5—As1—C2—C1	75.0 (2)
O6—P2—C1—O7	−53.90 (19)	C3—As1—C2—C1	−50.9 (2)
O4—P2—C1—O7	−173.37 (17)	C4—As1—C2—C1	−168.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6^i	0.81 (2)	1.69 (2)	2.486 (4)	165 (4)
O8—H17···O6^ii	0.81 (2)	1.95 (2)	2.759 (4)	174 (4)
O7—H4···O2^iii	0.83 (2)	1.98 (2)	2.759 (4)	157 (3)
O5—H3···O3^iii	0.86 (2)	1.62 (2)	2.471 (4)	171 (3)
O8—H16···O2	0.83 (2)	1.93 (2)	2.747 (4)	169 (4)
O4—H2···O8^iv	0.84 (2)	1.69 (2)	2.514 (3)	166 (4)

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