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

The title compound, C₁₀H₁₁N₂O₂P·H₂O, contains a tetra­coordinate penta­valent P atom. The phosphinate group plays a predominant role in the cohesion of the crystal structure by forming chains along the b axis via inter­molecular 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_r = 240.19

• Monoclinic, P 2₁ /n

• a = 6.7946 (5) Å

• b = 24.753 (2) Å

• c = 7.5277 (7) Å

• β = 114.433 (1)°

• V = 1152.70 (17) ų

• 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[F² > 2σ(F²)] = 0.054

• wR(F²) = 0.154

• S = 1.02

• 2597 reflections

• 146 parameters

• H-atom parameters constrained

• Δρ_max = 0.32 e Å⁻³

• Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1^i	0.85	1.86	2.709 (3)	174
C10—H10B⋯O1^ii	0.96	2.51	3.268 (4)	136
N2—H20⋯O3^iii	0.87	1.82	2.665 (3)	162
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y, z+1; (iii) x+1, y, z.

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.

Supporting information

S1. Comment

Phosphorylated imidazoles have attracted the attention of chemists and biochemists in the past decades because they are promising as synthons, pesticides, and drugs (Matevosyan & Zavlin, 1990). Pyridylphosphanes are well-established P—N ligands in transition metal chemistry (Grotjahn, 2010) while phosphinic acids have found use in the construction of coordination polymers for a wide range of applications (Kunz & Frank, 2010). The title compound, C₁₀H₁₃N₂O₃P, contains a tetracoordinate pentavalent P atom and the phosphinic function plays a predominant role in the cohesion of the crystal structure, both by forming chains along the b axis via weak intermolecular C—H···O hydrogen bonds and by connecting these chains by O—H···O and N—H···O hydrogen bonding with the lattice water molecules. The O—H···O and C—H···O interactions form 12-membered hydrogen bonded rings that are located on centers of inversion (Kunz & Frank, 2010) while the O—H···O and N—H···O interaction form 14-membered hydrogen bonded rings (Fig. 2).

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).

S2. Experimental

Triethylamine (14.74 mmol) was added dropwise at 0°C to dichlorophenylphosphine (7.37 mmol) dissolved in dichloromethane (10 ml) and the mixture was stirred for 10 min. Methylimidazole (14.74 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 10 h. After removal of the solvent, ethanol (30 ml) and sodium hydroxide (14.74 mmol) were added and the mixture stirred for 3 h. The solvent was removed in vacuo, dichloromethane (10 ml) was added, the precipitate was filtered off and the solvent removed in vacuo to give the crude product (2,2'-(phenylphosphinediyl)bis(1-methyl-1H-imidazole)). Butyl ether was used to recrystallize. Single crystals of the title compound suitable for X–ray diffraction were obtained by slow evaporation of a methanol solution of the product.

S3. Refinement

All H atoms attached to C, N and O atoms were fixed geometrically and treated as riding with C—H = 0.93–0.96 Å, O—H = 0.85 Å, N—H = 0.87 Å, with U_iso(H) = 1.5 U_eq(methyl) and U_iso(H) = 1.2 U_eq(C) for all other H atoms.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The two–dimensional plane, linked by C—H···O, N—H···O and O—H···O interactions.

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

Crystal data

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) Å^3	0.40 × 0.31 × 0.14 mm
Z = 4

Data collection

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

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0721P)^2 + 0.0591P] where P = (Fo^2 + 2Fc^2)/3
2597 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1^i	0.85	1.86	2.709 (3)	174
C10—H10B···O1^ii	0.96	2.51	3.268 (4)	136
N2—H20···O3^iii	0.87	1.82	2.665 (3)	162

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