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

Sun, Y.-M.; Yang, M.; Zhao, C.-Q.

doi:10.1107/S1600536812028255

organic compounds

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Volume 68| Part 8| August 2012| Page o2330

https://doi.org/10.1107/S1600536812028255

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

Yong-Ming Sun,^a Meng Yang ^a and Chang-Qiu Zhao ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: literabc@hotmail.com

(Received 16 May 2012; accepted 21 June 2012; online 4 July 2012)

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) 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[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⋯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) -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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812028255/mw2070sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028255/mw2070Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812028255/mw2070Isup3.cml

checkCIF report

Comment top

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 top

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 top

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.

Structure description top

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).

Computing details top

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 top

	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 top

Crystal data top

C₁₀H₁₁N₂O₂P·H₂O	F(000) = 504
M_r = 240.19	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0721P)² + 0.0591P] where P = (F_o² + 2F_c²)/3
2597 reflections	(Δ/σ)_max = 0.001
146 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₀H₁₁N₂O₂P·H₂O	V = 1152.70 (17) Å³
M_r = 240.19	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.7946 (5) Å	µ = 0.23 mm⁻¹
b = 24.753 (2) Å	T = 298 K
c = 7.5277 (7) Å	0.40 × 0.31 × 0.14 mm
β = 114.433 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2597 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1489 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.968	R_int = 0.048
6904 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.02	Δρ_max = 0.32 e Å⁻³
2597 reflections	Δρ_min = −0.31 e Å⁻³
146 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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)

Geometric parameters (Å, º) top

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) top

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) −x+1, −y, −z; (ii) x, y, z+1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁N₂O₂P·H₂O
M_r	240.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.7946 (5), 24.753 (2), 7.5277 (7)
β (°)	114.433 (1)
V (Å³)	1152.70 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.31 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.913, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	6904, 2597, 1489
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.154, 1.02
No. of reflections	2597
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.31

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z; (ii) x, y, z+1; (iii) x+1, y, z.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20772055) for financial support of this study.

References

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