Benz-yl(meth-yl)phosphinic acid.

The title compound, C(8)H(11)O(2)P, is a phosphinic compound with a tetra-coordinate penta-valent P atom. The phosphinic function plays a predominant role in the cohesion of the crystal structure, both by forming chains along the b axis via strong inter-molecular O-H⋯O hydrogen bonds and by cross-linking these chains perpendicularly via weak inter-molecular C-H⋯O hydrogen bonds, generating a two-dimensional network parallel to (001).

Related literature

For general background to phosphinic compounds and their biological applications, see: Ye et al. (2007 ▶); Abrunhosa-Thomas et al. (2007 ▶); Wang et al. (2009 ▶). For their inhibitor properties and use as anti­bacterial agents, see: Boyd et al. (1994 ▶); Matziari et al. (2004 ▶); Ryglowski & Kafarski (1996 ▶). For the preparation of phosphinic acid, see: Montchamp (2005 ▶); Dingwall et al. (1989 ▶); Fougère et al. (2009 ▶). For related structures, see: Frantz et al. (2003 ▶); Langley et al. (1996 ▶); Cai et al. (2003 ▶); Meyer et al. (2003 ▶).

Experimental

Crystal data

C8H11O2P

M = 170.14

Monoclinic,

a = 9.3075 (4) Å

b = 8.2526 (4) Å

c = 11.8890 (4) Å

β = 108.657 (3)°

V = 865.22 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.60 × 0.25 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

10548 measured reflections

1767 independent reflections

1320 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.096

S = 1.05

1767 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: HKL (Otwinowski & Minor, 1997 ▶); data reduction: COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and CrystalBuilder (Welter, 2006 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024116/dn2573sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024116/dn2573Isup2.hkl

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

C8H11O2P	F(000) = 360
Mr = 170.14	Dx = 1.306 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 1896 reflections
a = 9.3075 (4) Å	θ = 0.4–26.4°
b = 8.2526 (4) Å	µ = 0.27 mm−1
c = 11.8890 (4) Å	T = 293 K
β = 108.657 (3)°	Parallelepipedic, colourless
V = 865.22 (6) Å3	0.60 × 0.25 × 0.06 mm
Z = 4

Nonius KappaCCD diffractometer	1320 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
graphite	θmax = 26.3°, θmin = 2.3°
Detector resolution: 9 pixels mm-1	h = −11→11
φ and ω scans	k = −10→10
10548 measured reflections	l = −14→14
1767 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0381P)2 + 0.2898P] where P = (Fo2 + 2Fc2)/3
1767 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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. 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	0.37056 (5)	0.18896 (6)	0.22698 (4)	0.03697 (18)
C1	0.3422 (3)	0.2500 (3)	0.36151 (18)	0.0574 (6)
H11	0.3450	0.1566	0.4103	0.086*
H12	0.2454	0.3023	0.3441	0.086*
H13	0.4209	0.3241	0.4029	0.086*
O1	0.36315 (16)	0.34293 (17)	0.15063 (12)	0.0487 (4)
H1	0.4189	0.4128	0.1909	0.058*
O2	0.51352 (16)	0.09571 (18)	0.24906 (16)	0.0606 (4)
C2	0.2113 (2)	0.0707 (2)	0.14174 (19)	0.0440 (5)
H21	0.2228	0.0488	0.0649	0.066*
H22	0.2144	−0.0326	0.1814	0.066*
C3	0.0567 (2)	0.1455 (2)	0.12169 (17)	0.0376 (5)
C4	−0.0016 (3)	0.2590 (3)	0.03332 (17)	0.0485 (5)
H4	0.0557	0.2914	−0.0140	0.058*
C5	−0.1435 (3)	0.3248 (3)	0.0144 (2)	0.0618 (7)
H5	−0.1812	0.4011	−0.0454	0.074*
C6	−0.2295 (3)	0.2779 (3)	0.0838 (2)	0.0640 (7)
H6	−0.3255	0.3218	0.0709	0.077*
C7	−0.1734 (3)	0.1669 (3)	0.1716 (2)	0.0613 (7)
H7	−0.2312	0.1352	0.2187	0.074*
C8	−0.0310 (2)	0.1011 (3)	0.19124 (19)	0.0509 (6)
H8	0.0064	0.0260	0.2519	0.061*

	U11	U22	U33	U12	U13	U23
P1	0.0327 (3)	0.0317 (3)	0.0455 (3)	0.0038 (2)	0.0113 (2)	0.0036 (2)
C1	0.0587 (14)	0.0668 (16)	0.0453 (12)	−0.0012 (12)	0.0147 (10)	0.0005 (12)
O1	0.0563 (9)	0.0378 (9)	0.0471 (8)	−0.0077 (7)	0.0097 (6)	0.0053 (6)
O2	0.0367 (8)	0.0452 (9)	0.0993 (12)	0.0114 (7)	0.0209 (8)	0.0051 (9)
C2	0.0418 (11)	0.0336 (11)	0.0557 (12)	−0.0018 (9)	0.0143 (9)	−0.0032 (9)
C3	0.0343 (10)	0.0351 (11)	0.0406 (10)	−0.0066 (8)	0.0081 (8)	−0.0062 (8)
C4	0.0508 (12)	0.0475 (13)	0.0442 (11)	−0.0013 (11)	0.0111 (10)	0.0027 (10)
C5	0.0581 (15)	0.0499 (15)	0.0602 (14)	0.0081 (12)	−0.0050 (11)	−0.0017 (12)
C6	0.0364 (12)	0.0625 (17)	0.0836 (17)	0.0008 (12)	0.0061 (12)	−0.0282 (15)
C7	0.0463 (13)	0.0689 (17)	0.0751 (16)	−0.0124 (13)	0.0284 (12)	−0.0164 (14)
C8	0.0471 (13)	0.0531 (14)	0.0525 (12)	−0.0080 (11)	0.0159 (10)	0.0034 (11)

P1—O2	1.4859 (14)	C3—C4	1.382 (3)
P1—O1	1.5502 (14)	C3—C8	1.384 (3)
P1—C1	1.775 (2)	C4—C5	1.378 (3)
P1—C2	1.793 (2)	C4—H4	0.9300
C1—H11	0.9600	C5—C6	1.377 (4)
C1—H12	0.9600	C5—H5	0.9300
C1—H13	0.9600	C6—C7	1.361 (4)
O1—H1	0.8200	C6—H6	0.9300
C2—C3	1.514 (3)	C7—C8	1.381 (3)
C2—H21	0.9700	C7—H7	0.9300
C2—H22	0.9700	C8—H8	0.9300
O2—P1—O1	113.42 (9)	C4—C3—C8	118.07 (19)
O2—P1—C1	111.74 (11)	C4—C3—C2	121.23 (18)
O1—P1—C1	107.66 (10)	C8—C3—C2	120.70 (18)
O2—P1—C2	110.46 (9)	C5—C4—C3	120.9 (2)
O1—P1—C2	103.96 (9)	C5—C4—H4	119.5
C1—P1—C2	109.24 (10)	C3—C4—H4	119.5
P1—C1—H11	109.5	C6—C5—C4	120.1 (2)
P1—C1—H12	109.5	C6—C5—H5	119.9
H11—C1—H12	109.5	C4—C5—H5	119.9
P1—C1—H13	109.5	C7—C6—C5	119.6 (2)
H11—C1—H13	109.5	C7—C6—H6	120.2
H12—C1—H13	109.5	C5—C6—H6	120.2
P1—O1—H1	109.5	C6—C7—C8	120.5 (2)
C3—C2—P1	116.08 (14)	C6—C7—H7	119.8
C3—C2—H21	108.3	C8—C7—H7	119.8
P1—C2—H21	108.3	C7—C8—C3	120.8 (2)
C3—C2—H22	108.3	C7—C8—H8	119.6
P1—C2—H22	108.3	C3—C8—H8	119.6
H21—C2—H22	107.4
O2—P1—C2—C3	174.91 (15)	C3—C4—C5—C6	0.0 (3)
O1—P1—C2—C3	−63.09 (17)	C4—C5—C6—C7	0.3 (4)
C1—P1—C2—C3	51.61 (18)	C5—C6—C7—C8	−0.1 (4)
P1—C2—C3—C4	81.4 (2)	C6—C7—C8—C3	−0.5 (4)
P1—C2—C3—C8	−99.0 (2)	C4—C3—C8—C7	0.8 (3)
C8—C3—C4—C5	−0.6 (3)	C2—C3—C8—C7	−178.8 (2)
C2—C3—C4—C5	179.01 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.70	2.493 (2)	162
C7—H7···O2ii	0.93	2.54	3.377 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.70	2.493 (2)	162
C7—H7⋯O2ii	0.93	2.54	3.377 (3)	151

Symmetry codes: (i) ; (ii) .