(1-Methyl-1H-imidazol-3-ium-2-yl)(phen-yl)phosphinate monohydrate.

The title compound, C(10)H(11)N(2)O(2)P·H(2)O, contains a tetra-coordinate penta-valent P atom. The phosphinate group plays a predominant role in the cohesion of the crystal structure by forming chains along the b axis via inter-molecular C-H⋯O hydrogen bonds. These chains are connected by O-H⋯O and N-H⋯O hydrogen bonding involving the lattice water.

Related literature

For background infomation on phospho­rylated imidazoles, see: Andrej et al. (1999 ▶); Matevosyan & Zavlin (1990 ▶); Grotjahn (2010 ▶). For the structures of related imidazolyl phosphinic acids and the function of phospho­rylated imidazoles, see: Kunz & Frank (2010 ▶).

Experimental

Crystal data

C10H11N2O2P·H2O

M = 240.19

Monoclinic,

a = 6.7946 (5) Å

b = 24.753 (2) Å

c = 7.5277 (7) Å

β = 114.433 (1)°

V = 1152.70 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 298 K

0.40 × 0.31 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.913, T max = 0.968

6904 measured reflections

2597 independent reflections

1489 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.154

S = 1.02

2597 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028255/mw2070sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028255/mw2070Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028255/mw2070Isup3.cml

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

C10H11N2O2P·H2O	F(000) = 504
Mr = 240.19	Dx = 1.384 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1313 reflections
a = 6.7946 (5) Å	θ = 2.5–23.3°
b = 24.753 (2) Å	µ = 0.23 mm−1
c = 7.5277 (7) Å	T = 298 K
β = 114.433 (1)°	Block, colourless
V = 1152.70 (17) Å3	0.40 × 0.31 × 0.14 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2597 independent reflections
Radiation source: fine-focus sealed tube	1489 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.913, Tmax = 0.968	k = −29→32
6904 measured reflections	l = −9→7

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0721P)2 + 0.0591P] where P = (Fo2 + 2Fc2)/3
2597 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.32 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	0.73237 (13)	0.10122 (3)	0.11830 (10)	0.0428 (3)
O1	0.8280 (4)	0.07348 (9)	−0.0024 (3)	0.0608 (7)
O2	0.5092 (3)	0.09076 (9)	0.0956 (3)	0.0578 (6)
N1	0.8906 (4)	0.09159 (8)	0.5352 (3)	0.0346 (5)
N2	1.1068 (4)	0.06002 (9)	0.4191 (3)	0.0403 (6)
H20	1.1542	0.0490	0.3337	0.048*
C1	0.7732 (5)	0.17278 (12)	0.1149 (4)	0.0428 (7)
C2	0.9522 (5)	0.19315 (13)	0.0927 (5)	0.0562 (9)
H2	1.0506	0.1695	0.0775	0.067*
C3	0.9849 (7)	0.24800 (15)	0.0931 (6)	0.0784 (12)
H3	1.1050	0.2613	0.0778	0.094*
C4	0.8414 (8)	0.28317 (15)	0.1158 (6)	0.0796 (12)
H4	0.8644	0.3202	0.1153	0.096*
C5	0.6659 (7)	0.26430 (14)	0.1391 (6)	0.0727 (11)
H5	0.5698	0.2884	0.1557	0.087*
C6	0.6298 (5)	0.20933 (14)	0.1381 (5)	0.0580 (9)
H6	0.5086	0.1966	0.1529	0.070*
C7	0.9148 (4)	0.08320 (10)	0.3684 (4)	0.0331 (6)
C8	1.0715 (5)	0.07368 (11)	0.6899 (4)	0.0435 (7)
H8	1.0965	0.0750	0.8210	0.052*
C9	1.2055 (5)	0.05385 (12)	0.6160 (4)	0.0459 (7)
H9	1.3409	0.0387	0.6864	0.055*
C10	0.7023 (5)	0.11496 (13)	0.5516 (4)	0.0502 (8)
H10A	0.6580	0.1468	0.4721	0.075*
H10B	0.7382	0.1243	0.6852	0.075*
H10C	0.5864	0.0892	0.5083	0.075*
O3	0.3180 (3)	0.01614 (8)	0.2251 (3)	0.0536 (6)
H3A	0.2753	−0.0110	0.1494	0.080*
H3B	0.3774	0.0385	0.1767	0.080*

	U11	U22	U33	U12	U13	U23
P1	0.0533 (5)	0.0472 (5)	0.0242 (4)	−0.0145 (4)	0.0123 (3)	−0.0023 (3)
O1	0.0936 (18)	0.0620 (14)	0.0352 (12)	−0.0157 (12)	0.0352 (12)	−0.0120 (10)
O2	0.0458 (13)	0.0743 (15)	0.0405 (12)	−0.0237 (11)	0.0049 (10)	0.0042 (10)
N1	0.0410 (13)	0.0363 (13)	0.0267 (12)	0.0040 (10)	0.0141 (10)	0.0016 (9)
N2	0.0485 (15)	0.0392 (13)	0.0404 (14)	−0.0012 (11)	0.0256 (12)	−0.0044 (10)
C1	0.0460 (18)	0.0491 (17)	0.0261 (14)	−0.0061 (14)	0.0077 (13)	0.0049 (12)
C2	0.057 (2)	0.055 (2)	0.062 (2)	−0.0071 (16)	0.0288 (18)	0.0050 (16)
C3	0.081 (3)	0.062 (3)	0.097 (3)	−0.021 (2)	0.042 (3)	0.011 (2)
C4	0.100 (3)	0.049 (2)	0.086 (3)	−0.008 (2)	0.035 (3)	0.011 (2)
C5	0.076 (3)	0.057 (2)	0.085 (3)	0.017 (2)	0.033 (2)	0.0152 (19)
C6	0.052 (2)	0.063 (2)	0.055 (2)	0.0026 (17)	0.0188 (17)	0.0143 (16)
C7	0.0410 (16)	0.0315 (14)	0.0298 (15)	−0.0055 (12)	0.0176 (13)	−0.0046 (11)
C8	0.0488 (18)	0.0485 (17)	0.0273 (15)	0.0014 (14)	0.0098 (14)	0.0058 (12)
C9	0.0415 (17)	0.0509 (18)	0.0411 (17)	0.0036 (14)	0.0128 (14)	0.0055 (14)
C10	0.055 (2)	0.060 (2)	0.0399 (17)	0.0137 (16)	0.0243 (15)	0.0035 (14)
O3	0.0665 (15)	0.0514 (13)	0.0562 (14)	−0.0079 (10)	0.0388 (12)	−0.0118 (10)

P1—O2	1.477 (2)	C3—H3	0.9300
P1—O1	1.486 (2)	C4—C5	1.358 (5)
P1—C1	1.795 (3)	C4—H4	0.9300
P1—C7	1.830 (3)	C5—C6	1.382 (5)
N1—C7	1.348 (3)	C5—H5	0.9300
N1—C8	1.371 (3)	C6—H6	0.9300
N1—C10	1.455 (3)	C8—C9	1.341 (4)
N2—C7	1.329 (3)	C8—H8	0.9300
N2—C9	1.359 (3)	C9—H9	0.9300
N2—H20	0.8730	C10—H10A	0.9600
C1—C2	1.389 (4)	C10—H10B	0.9600
C1—C6	1.393 (4)	C10—H10C	0.9600
C2—C3	1.376 (4)	O3—H3A	0.8502
C2—H2	0.9300	O3—H3B	0.8510
C3—C4	1.369 (5)
O2—P1—O1	122.39 (13)	C3—C4—H4	119.8
O2—P1—C1	109.20 (14)	C4—C5—C6	120.1 (4)
O1—P1—C1	109.76 (13)	C4—C5—H5	120.0
O2—P1—C7	107.60 (12)	C6—C5—H5	120.0
O1—P1—C7	103.61 (13)	C5—C6—C1	120.6 (3)
C1—P1—C7	102.25 (12)	C5—C6—H6	119.7
C7—N1—C8	109.3 (2)	C1—C6—H6	119.7
C7—N1—C10	126.2 (2)	N2—C7—N1	106.4 (2)
C8—N1—C10	124.5 (2)	N2—C7—P1	124.5 (2)
C7—N2—C9	110.1 (2)	N1—C7—P1	129.0 (2)
C7—N2—H20	122.7	C9—C8—N1	106.8 (3)
C9—N2—H20	127.0	C9—C8—H8	126.6
C2—C1—C6	118.2 (3)	N1—C8—H8	126.6
C2—C1—P1	120.6 (2)	C8—C9—N2	107.4 (2)
C6—C1—P1	121.3 (2)	C8—C9—H9	126.3
C3—C2—C1	120.5 (3)	N2—C9—H9	126.3
C3—C2—H2	119.8	N1—C10—H10A	109.5
C1—C2—H2	119.8	N1—C10—H10B	109.5
C4—C3—C2	120.3 (4)	H10A—C10—H10B	109.5
C4—C3—H3	119.8	N1—C10—H10C	109.5
C2—C3—H3	119.8	H10A—C10—H10C	109.5
C5—C4—C3	120.4 (4)	H10B—C10—H10C	109.5
C5—C4—H4	119.8	H3A—O3—H3B	108.5
O2—P1—C1—C2	−166.5 (2)	C9—N2—C7—P1	177.64 (19)
O1—P1—C1—C2	−29.7 (3)	C8—N1—C7—N2	0.5 (3)
C7—P1—C1—C2	79.8 (3)	C10—N1—C7—N2	−178.4 (2)
O2—P1—C1—C6	14.8 (3)	C8—N1—C7—P1	−177.3 (2)
O1—P1—C1—C6	151.5 (2)	C10—N1—C7—P1	3.7 (4)
C7—P1—C1—C6	−99.0 (2)	O2—P1—C7—N2	142.8 (2)
C6—C1—C2—C3	−0.2 (5)	O1—P1—C7—N2	11.9 (3)
P1—C1—C2—C3	−179.0 (3)	C1—P1—C7—N2	−102.2 (2)
C1—C2—C3—C4	0.2 (6)	O2—P1—C7—N1	−39.7 (3)
C2—C3—C4—C5	0.3 (6)	O1—P1—C7—N1	−170.6 (2)
C3—C4—C5—C6	−0.6 (6)	C1—P1—C7—N1	75.3 (3)
C4—C5—C6—C1	0.5 (5)	C7—N1—C8—C9	−0.5 (3)
C2—C1—C6—C5	−0.1 (4)	C10—N1—C8—C9	178.5 (3)
P1—C1—C6—C5	178.7 (3)	N1—C8—C9—N2	0.3 (3)
C9—N2—C7—N1	−0.3 (3)	C7—N2—C9—C8	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1i	0.85	1.86	2.709 (3)	174
C10—H10B···O1ii	0.96	2.51	3.268 (4)	136
N2—H20···O3iii	0.87	1.82	2.665 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1i	0.85	1.86	2.709 (3)	174
C10—H10B⋯O1ii	0.96	2.51	3.268 (4)	136
N2—H20⋯O3iii	0.87	1.82	2.665 (3)	162

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