The betainic form of (imidazol-2-yl)phenylphosphinic acid hydrate.

Single crystals of the title compound, (imidazolium-2-yl)phenyl-phosphinate monohydrate, C(9)H(9)N(2)O(2)·H(2)O, were ob-tained from methanol/water after deprotection and oxidation of bis-(1-diethoxy-methyl-imidazol-2-yl)phenyl-phosphane. In the structure, several N-H⋯O and P-O⋯H-O hydrogen bonds are found. π-π inter-actions between the protonated imidazolyl rings [centroid-centroid distance = 3.977 (2) Å] help to establish the crystal packing. The hydrate water mol-ecule builds hydrogen bridges to three mol-ecules of the phosphinic acid by the O and both H atoms.

Related literature

For structures of related imidazolyl phosphinic acids, see: Ball et al. (1984 ▶); Britten et al. (1993 ▶). For the chemistry of imidazolyl phosphanes, see: Enders et al. (2004 ▶); Kimblin et al. (1996a ▶,b ▶, 2000a ▶,b ▶); Kunz et al. (2003 ▶).

Experimental

Crystal data

C9H9N2O2P·H2O

M = 226.17

Monoclinic,

a = 8.5890 (6) Å

b = 12.1091 (7) Å

c = 10.9534 (7) Å

β = 111.766 (7)°

V = 1057.99 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 223 K

0.2 × 0.2 × 0.2 mm

Data collection

Stoe IPDS diffractometer

14882 measured reflections

2069 independent reflections

1606 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.092

S = 0.93

2069 reflections

148 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.16 e Å−3

Data collection: EXPOSE in IPDS Software (Stoe & Cie, 2000 ▶); cell refinement: CELL in IPDS Software; data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018337/nc2181sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018337/nc2181Isup2.hkl

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

C9H9N2O2P·H2O	F(000) = 472
Mr = 226.17	Dx = 1.420 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.5890 (6) Å	Cell parameters from 8000 reflections
b = 12.1091 (7) Å	θ = 2.6–26.1°
c = 10.9534 (7) Å	µ = 0.25 mm−1
β = 111.766 (7)°	T = 223 K
V = 1057.99 (12) Å3	Isometric, colourless
Z = 4	0.2 × 0.2 × 0.2 mm

Stoe IPDS diffractometer	1606 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
graphite	θmax = 26.1°, θmin = 2.6°
Detector resolution: 6.67 pixels mm-1	h = −10→10
φ–scans	k = −14→14
14882 measured reflections	l = −13→13
2069 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0664P)2] where P = (Fo2 + 2Fc2)/3
2069 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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 > σ(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	0.21068 (5)	0.75986 (4)	0.66209 (4)	0.02580 (15)
O1	0.38922 (15)	0.77558 (11)	0.74699 (13)	0.0357 (3)
O2	0.11462 (16)	0.84520 (10)	0.56559 (13)	0.0348 (3)
O3	−0.03925 (18)	1.01453 (13)	0.64926 (14)	0.0353 (3)
H3	0.007 (3)	0.965 (2)	0.622 (3)	0.054 (7)*
H4	−0.068 (3)	1.063 (3)	0.596 (3)	0.061 (8)*
N1	0.11416 (18)	0.61686 (12)	0.44158 (15)	0.0296 (3)
H1	0.0343	0.6596	0.3921	0.044*
N2	0.3181 (2)	0.55296 (12)	0.60673 (16)	0.0329 (4)
H2	0.399 (3)	0.5492 (17)	0.689 (2)	0.037 (6)*
C1	0.2123 (2)	0.63787 (14)	0.56488 (18)	0.0269 (4)
C2	0.1578 (3)	0.51769 (16)	0.4043 (2)	0.0383 (5)
H10	0.1080	0.4839	0.3216	0.057*
C3	0.2853 (3)	0.47751 (16)	0.5081 (2)	0.0403 (5)
H11	0.3412	0.4101	0.5119	0.060*
C4	0.0927 (2)	0.71894 (14)	0.76010 (18)	0.0276 (4)
C5	−0.0757 (2)	0.74606 (15)	0.7218 (2)	0.0346 (4)
H5	−0.1292	0.7856	0.6435	0.052*
C6	−0.1654 (2)	0.71519 (18)	0.7985 (2)	0.0430 (5)
H6	−0.2793	0.7341	0.7726	0.064*
C7	−0.0874 (3)	0.65688 (18)	0.9125 (2)	0.0436 (5)
H7	−0.1482	0.6361	0.9646	0.065*
C8	0.0794 (3)	0.62866 (18)	0.9510 (2)	0.0428 (5)
H8	0.1316	0.5883	1.0289	0.064*
C9	0.1702 (2)	0.65964 (17)	0.87531 (19)	0.0356 (4)
H9	0.2841	0.6406	0.9018	0.053*

	U11	U22	U33	U12	U13	U23
P1	0.0274 (2)	0.0255 (2)	0.0236 (3)	−0.00120 (16)	0.00835 (18)	−0.00096 (18)
O1	0.0315 (7)	0.0423 (7)	0.0312 (8)	−0.0076 (5)	0.0094 (6)	−0.0054 (6)
O2	0.0456 (7)	0.0294 (6)	0.0305 (8)	0.0057 (5)	0.0154 (6)	0.0035 (5)
O3	0.0428 (8)	0.0301 (7)	0.0295 (8)	0.0019 (6)	0.0092 (6)	−0.0007 (6)
N1	0.0308 (8)	0.0275 (7)	0.0265 (8)	0.0012 (6)	0.0060 (6)	0.0000 (6)
N2	0.0359 (8)	0.0303 (8)	0.0280 (9)	0.0054 (6)	0.0067 (7)	0.0014 (7)
C1	0.0259 (8)	0.0270 (9)	0.0263 (10)	0.0004 (6)	0.0080 (7)	0.0029 (7)
C2	0.0490 (11)	0.0325 (9)	0.0296 (10)	−0.0005 (8)	0.0104 (9)	−0.0088 (8)
C3	0.0495 (11)	0.0293 (10)	0.0380 (12)	0.0088 (8)	0.0116 (9)	−0.0036 (8)
C4	0.0310 (9)	0.0259 (8)	0.0260 (10)	−0.0017 (6)	0.0108 (7)	−0.0034 (7)
C5	0.0321 (9)	0.0321 (9)	0.0387 (11)	0.0035 (7)	0.0122 (8)	0.0000 (8)
C6	0.0351 (10)	0.0423 (11)	0.0571 (14)	−0.0004 (8)	0.0236 (10)	−0.0070 (10)
C7	0.0476 (11)	0.0486 (12)	0.0450 (13)	−0.0119 (9)	0.0291 (10)	−0.0092 (10)
C8	0.0453 (11)	0.0516 (12)	0.0316 (11)	−0.0100 (9)	0.0145 (9)	0.0042 (9)
C9	0.0317 (9)	0.0416 (10)	0.0316 (11)	−0.0012 (7)	0.0095 (8)	0.0045 (8)

P1—O1	1.4815 (13)	C2—H10	0.9400
P1—O2	1.4897 (13)	C3—H11	0.9400
P1—C4	1.7974 (18)	C4—C5	1.388 (3)
P1—C1	1.8240 (18)	C4—C9	1.389 (3)
O3—H3	0.83 (3)	C5—C6	1.385 (3)
O3—H4	0.79 (3)	C5—H5	0.9400
N1—C1	1.325 (2)	C6—C7	1.373 (3)
N1—C2	1.365 (2)	C6—H6	0.9400
N1—H1	0.8700	C7—C8	1.377 (3)
N2—C1	1.335 (2)	C7—H7	0.9400
N2—C3	1.362 (2)	C8—C9	1.385 (3)
N2—H2	0.91 (2)	C8—H8	0.9400
C2—C3	1.344 (3)	C9—H9	0.9400
O1—P1—O2	121.89 (8)	C2—C3—H11	126.5
O1—P1—C4	110.00 (8)	N2—C3—H11	126.5
O2—P1—C4	109.18 (8)	C5—C4—C9	119.45 (17)
O1—P1—C1	103.90 (8)	C5—C4—P1	120.62 (14)
O2—P1—C1	105.65 (8)	C9—C4—P1	119.93 (13)
C4—P1—C1	104.68 (8)	C6—C5—C4	120.30 (19)
H3—O3—H4	109 (3)	C6—C5—H5	119.8
C1—N1—C2	109.43 (15)	C4—C5—H5	119.8
C1—N1—H1	125.3	C7—C6—C5	119.77 (18)
C2—N1—H1	125.3	C7—C6—H6	120.1
C1—N2—C3	109.27 (16)	C5—C6—H6	120.1
C1—N2—H2	123.3 (14)	C6—C7—C8	120.50 (19)
C3—N2—H2	127.4 (14)	C6—C7—H7	119.7
N1—C1—N2	107.26 (16)	C8—C7—H7	119.7
N1—C1—P1	127.65 (13)	C7—C8—C9	120.1 (2)
N2—C1—P1	125.07 (14)	C7—C8—H8	119.9
C3—C2—N1	107.04 (17)	C9—C8—H8	119.9
C3—C2—H10	126.5	C8—C9—C4	119.84 (18)
N1—C2—H10	126.5	C8—C9—H9	120.1
C2—C3—N2	106.99 (17)	C4—C9—H9	120.1
C2—N1—C1—N2	−0.1 (2)	O2—P1—C4—C5	14.52 (17)
C2—N1—C1—P1	178.80 (14)	C1—P1—C4—C5	−98.21 (15)
C3—N2—C1—N1	−0.1 (2)	O1—P1—C4—C9	−29.28 (17)
C3—N2—C1—P1	−179.06 (14)	O2—P1—C4—C9	−165.48 (14)
O1—P1—C1—N1	−145.99 (16)	C1—P1—C4—C9	81.80 (16)
O2—P1—C1—N1	−16.61 (18)	C9—C4—C5—C6	0.6 (3)
C4—P1—C1—N1	98.60 (17)	P1—C4—C5—C6	−179.36 (15)
O1—P1—C1—N2	32.72 (18)	C4—C5—C6—C7	−0.4 (3)
O2—P1—C1—N2	162.09 (15)	C5—C6—C7—C8	−0.1 (3)
C4—P1—C1—N2	−82.69 (17)	C6—C7—C8—C9	0.4 (3)
C1—N1—C2—C3	0.3 (2)	C7—C8—C9—C4	−0.2 (3)
N1—C2—C3—N2	−0.3 (2)	C5—C4—C9—C8	−0.3 (3)
C1—N2—C3—C2	0.3 (2)	P1—C4—C9—C8	179.68 (16)
O1—P1—C4—C5	150.71 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87	1.80	2.6302 (19)	160
N2—H2···O3ii	0.91 (2)	1.78 (2)	2.684 (2)	168 (2)
O3—H3···O2	0.83 (3)	1.94 (3)	2.773 (2)	177 (3)
O3—H4···O2iii	0.79 (3)	2.00 (3)	2.777 (2)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87	1.80	2.6302 (19)	160
N2—H2⋯O3ii	0.91 (2)	1.78 (2)	2.684 (2)	168 (2)
O3—H3⋯O2	0.83 (3)	1.94 (3)	2.773 (2)	177 (3)
O3—H4⋯O2iii	0.79 (3)	2.00 (3)	2.777 (2)	164 (3)

Symmetry codes: (i) ; (ii) ; (iii) .