[1-Hydr­oxy-1-phosphono-2-(trimethyl­phospho­nium-1-yl)eth­yl]phospho­nate monohydrate

The title compound, C₅H₁₅O₇P₃·H₂O, crystallizes as a zwitterionic monohydrate and forms a layer structure with water mol­ecules hydrogen bonded to the phospho­nate groups.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.092
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm

   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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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-(trimethylphosphonium-1-yl)ethyl]phosphonate monohydrate

Crystal data

C5H15O7P3·H2O	F(000) = 624
Mr = 298.10	Dx = 1.595 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 938 reflections
a = 7.165 (2) Å	θ = 3.5–28.1°
b = 10.545 (4) Å	µ = 0.50 mm^−1
c = 16.613 (6) Å	T = 193 K
β = 98.475 (5)°	Plate, colorless
V = 1241.6 (7) Å^3	0.70 × 0.24 × 0.03 mm
Z = 4

Data collection

Siemens Platform/CCD diffractometer	3055 independent reflections
Radiation source: normal-focus sealed tube	2379 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Profile data from ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: integration (SHELXTL/XPREP; Bruker, 2001)	h = −9→9
Tmin = 0.814, Tmax = 0.985	k = −14→14
12219 measured reflections	l = −22→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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 0.4585P] where P = (Fo^2 + 2Fc^2)/3
3055 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.41 e Å^−3
8 restraints	Δρmin = −0.31 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 P1, P2, and P3; 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
C1	0.3856 (2)	0.86178 (17)	0.27958 (11)	0.0175 (4)
C2	0.2968 (3)	0.74517 (18)	0.31708 (11)	0.0208 (4)
H1	0.352 (3)	0.6664 (17)	0.3042 (13)	0.025*
H2	0.161 (2)	0.737 (2)	0.2988 (13)	0.025*
C3	0.2178 (4)	0.5882 (2)	0.44715 (14)	0.0404 (6)
H3	0.2238	0.5775	0.5061	0.061*
H4	0.2957	0.5233	0.4261	0.061*
H5	0.0868	0.5795	0.4208	0.061*
C4	0.1493 (4)	0.8580 (2)	0.45764 (14)	0.0380 (5)
H6	0.1438	0.8480	0.5159	0.057*
H7	0.0227	0.8468	0.4269	0.057*
H8	0.1960	0.9429	0.4474	0.057*
C5	0.5342 (4)	0.7577 (2)	0.48253 (14)	0.0401 (6)
H9	0.5881	0.8395	0.4700	0.060*
H10	0.6147	0.6890	0.4677	0.060*
H11	0.5266	0.7532	0.5409	0.060*
O1	0.7372 (2)	0.76143 (13)	0.32410 (9)	0.0258 (3)
H12	0.727 (4)	0.6829 (16)	0.3281 (16)	0.039*
O2	0.69703 (19)	0.93685 (14)	0.22312 (10)	0.0300 (3)
H13	0.809 (2)	0.935 (3)	0.2253 (17)	0.045*
O3	0.5721 (2)	0.71504 (13)	0.18113 (8)	0.0257 (3)
O4	0.1593 (2)	0.81800 (13)	0.13459 (8)	0.0247 (3)
H14	0.081 (3)	0.765 (2)	0.1445 (15)	0.037*
O5	0.30086 (19)	1.03090 (12)	0.15469 (8)	0.0226 (3)
O6	0.04508 (18)	0.96552 (13)	0.23834 (8)	0.0249 (3)
O7	0.4255 (2)	0.95532 (12)	0.34274 (8)	0.0220 (3)
H15	0.449 (3)	1.0248 (17)	0.3264 (15)	0.033*
O8	0.9185 (2)	0.64720 (14)	0.14180 (9)	0.0279 (3)
H16	0.938 (4)	0.588 (2)	0.1748 (14)	0.042*
H17	0.809 (3)	0.672 (2)	0.1452 (16)	0.042*
P1	0.21033 (7)	0.92654 (4)	0.19694 (3)	0.01798 (12)
P2	0.60806 (7)	0.81168 (5)	0.24725 (3)	0.02041 (13)
P3	0.30399 (8)	0.74214 (5)	0.42618 (3)	0.02532 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0195 (8)	0.0147 (8)	0.0184 (8)	−0.0008 (7)	0.0033 (7)	−0.0012 (7)
C2	0.0263 (10)	0.0194 (9)	0.0172 (9)	−0.0024 (8)	0.0049 (7)	0.0013 (7)
C3	0.0716 (17)	0.0276 (11)	0.0238 (11)	−0.0108 (11)	0.0129 (11)	0.0024 (9)
C4	0.0568 (15)	0.0307 (12)	0.0312 (12)	0.0030 (11)	0.0220 (11)	−0.0015 (9)
C5	0.0465 (14)	0.0488 (15)	0.0222 (11)	−0.0030 (11)	−0.0044 (10)	0.0045 (10)
O1	0.0262 (7)	0.0187 (7)	0.0307 (8)	0.0015 (6)	−0.0014 (6)	0.0012 (6)
O2	0.0178 (7)	0.0234 (7)	0.0496 (9)	0.0020 (6)	0.0074 (7)	0.0124 (6)
O3	0.0311 (8)	0.0242 (7)	0.0228 (7)	0.0061 (6)	0.0072 (6)	−0.0008 (6)
O4	0.0291 (8)	0.0242 (7)	0.0210 (7)	−0.0080 (6)	0.0049 (6)	−0.0042 (6)
O5	0.0268 (7)	0.0180 (7)	0.0237 (7)	−0.0007 (5)	0.0055 (6)	0.0031 (5)
O6	0.0191 (6)	0.0275 (7)	0.0284 (7)	0.0007 (6)	0.0042 (6)	−0.0020 (6)
O7	0.0304 (7)	0.0162 (6)	0.0191 (7)	−0.0039 (6)	0.0028 (6)	−0.0028 (5)
O8	0.0263 (7)	0.0237 (8)	0.0355 (9)	−0.0023 (6)	0.0105 (7)	0.0007 (6)
P1	0.0188 (2)	0.0171 (2)	0.0179 (2)	−0.00061 (18)	0.00249 (18)	−0.00017 (17)
P2	0.0196 (2)	0.0178 (2)	0.0245 (3)	0.00186 (18)	0.00535 (19)	0.00230 (19)
P3	0.0372 (3)	0.0221 (3)	0.0172 (2)	−0.0022 (2)	0.0055 (2)	0.00123 (19)

Geometric parameters (Å, º)

C1—O7	1.438 (2)	C5—H9	0.9800
C1—C2	1.556 (3)	C5—H10	0.9800
C1—P2	1.8331 (19)	C5—H11	0.9800
C1—P1	1.8494 (19)	O1—P2	1.5551 (15)
C2—P3	1.806 (2)	O1—H12	0.835 (17)
C2—H1	0.957 (15)	O2—P2	1.5443 (15)
C2—H2	0.980 (16)	O2—H13	0.796 (17)
C3—P3	1.789 (2)	O3—P2	1.4928 (15)
C3—H3	0.9800	O4—P1	1.5509 (14)
C3—H4	0.9800	O4—H14	0.830 (16)
C3—H5	0.9800	O5—P1	1.5029 (14)
C4—P3	1.779 (2)	O6—P1	1.5113 (15)
C4—H6	0.9800	O7—H15	0.807 (16)
C4—H7	0.9800	O8—H16	0.829 (17)
C4—H8	0.9800	O8—H17	0.836 (17)
C5—P3	1.780 (2)
O7—C1—C2	107.39 (14)	P3—C5—H11	109.5
O7—C1—P2	108.88 (12)	H9—C5—H11	109.5
C2—C1—P2	108.30 (12)	H10—C5—H11	109.5
O7—C1—P1	109.19 (12)	P2—O1—H12	110.8 (18)
C2—C1—P1	108.42 (12)	P2—O2—H13	114 (2)
P2—C1—P1	114.43 (10)	P1—O4—H14	118.0 (18)
C1—C2—P3	117.58 (13)	C1—O7—H15	113.9 (18)
C1—C2—H1	113.0 (13)	H16—O8—H17	105 (3)
P3—C2—H1	104.9 (13)	O5—P1—O6	115.75 (8)
C1—C2—H2	113.1 (13)	O5—P1—O4	107.70 (8)
P3—C2—H2	101.0 (13)	O6—P1—O4	112.41 (8)
H1—C2—H2	106.0 (18)	O5—P1—C1	108.93 (8)
P3—C3—H3	109.5	O6—P1—C1	104.74 (8)
P3—C3—H4	109.5	O4—P1—C1	106.91 (8)
H3—C3—H4	109.5	O3—P2—O2	115.19 (9)
P3—C3—H5	109.5	O3—P2—O1	112.88 (8)
H3—C3—H5	109.5	O2—P2—O1	106.62 (8)
H4—C3—H5	109.5	O3—P2—C1	110.43 (8)
P3—C4—H6	109.5	O2—P2—C1	103.87 (8)
P3—C4—H7	109.5	O1—P2—C1	107.18 (9)
H6—C4—H7	109.5	C4—P3—C5	110.58 (13)
P3—C4—H8	109.5	C4—P3—C3	108.53 (13)
H6—C4—H8	109.5	C5—P3—C3	107.52 (12)
H7—C4—H8	109.5	C4—P3—C2	110.84 (10)
P3—C5—H9	109.5	C5—P3—C2	114.41 (11)
P3—C5—H10	109.5	C3—P3—C2	104.59 (10)
H9—C5—H10	109.5
O7—C1—C2—P3	−10.4 (2)	O7—C1—P2—O3	−179.58 (11)
P2—C1—C2—P3	107.00 (14)	C2—C1—P2—O3	63.94 (14)
P1—C1—C2—P3	−128.30 (12)	P1—C1—P2—O3	−57.11 (12)
O7—C1—P1—O5	68.93 (13)	O7—C1—P2—O2	−55.54 (14)
C2—C1—P1—O5	−174.37 (11)	C2—C1—P2—O2	−172.02 (12)
P2—C1—P1—O5	−53.38 (12)	P1—C1—P2—O2	66.93 (12)
O7—C1—P1—O6	−55.48 (13)	O7—C1—P2—O1	57.09 (13)
C2—C1—P1—O6	61.22 (14)	C2—C1—P2—O1	−59.39 (13)
P2—C1—P1—O6	−177.79 (9)	P1—C1—P2—O1	179.56 (9)
O7—C1—P1—O4	−174.95 (11)	C1—C2—P3—C4	70.22 (18)
C2—C1—P1—O4	−58.25 (14)	C1—C2—P3—C5	−55.63 (18)
P2—C1—P1—O4	62.74 (11)	C1—C2—P3—C3	−173.00 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H17···O3	0.84 (2)	1.94 (2)	2.753 (2)	165 (3)
O8—H16···O6^i	0.83 (2)	1.93 (2)	2.748 (2)	170 (3)
O7—H15···O3^ii	0.81 (2)	2.01 (2)	2.768 (2)	155 (2)
O1—H12···O5^i	0.84 (2)	1.65 (2)	2.477 (2)	174 (3)
O2—H13···O6^iii	0.80 (2)	1.71 (2)	2.488 (2)	166 (3)
O4—H14···O8^iv	0.83 (2)	1.69 (2)	2.509 (2)	167 (3)

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