Meth-yl(phen-yl)phosphinic acid.

The crystal structure of the title compound, C(7)H(9)O(2)P, displays O-H⋯O hydrogen bonding , which links individual mol-ecules related via the c-glide plane and translational symmetry along the crystallographic b-axis direction into continuous chains.

Related literature

For background to phosphinic acids and their applications, see: Beckmann et al. (2009 ▶); Burrow et al. (2000 ▶); Burrow & Siqueira da Silva (2011 ▶); Chen & Suslick (1993 ▶); Siqueira et al. (2006 ▶); Vioux et al. (2004 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶) and for geometrical analysis using Mogul, see: Bruno et al. (2004 ▶).

Experimental

Crystal data

C7H9O2P

M = 156.11

Orthorhombic,

a = 12.4231 (8) Å

b = 7.8464 (5) Å

c = 15.9801 (10) Å

V = 1557.69 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.34 × 0.34 × 0.18 mm

Data collection

Bruker X8 Kappa APEXII diffractometer

Absorption correction: Gaussian (SADABS; Bruker 2009 ▶) T min = 0.668, T max = 0.950

19802 measured reflections

2342 independent reflections

1506 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.04

2342 reflections

95 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025530/zb2012sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025530/zb2012Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025530/zb2012Isup3.cml

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

C7H9O2P	Dx = 1.331 Mg m−3
Mr = 156.11	Melting point = 402–408 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 12.4231 (8) Å	Cell parameters from 788 reflections
b = 7.8464 (5) Å	θ = 2.5–22.7°
c = 15.9801 (10) Å	µ = 0.29 mm−1
V = 1557.69 (17) Å3	T = 296 K
Z = 8	Irregular block, colourless
F(000) = 656	0.34 × 0.34 × 0.18 mm

Bruker X8 Kappa APEXII diffractometer	2342 independent reflections
Radiation source: fine focus ceramic X-ray tube	1506 reflections with I > 2σ(I)
graphite	Rint = 0.057
Detector resolution: 8.3333 pixels mm-1	θmax = 30.5°, θmin = 3.0°
0.5° φ and ω scans	h = −17→16
Absorption correction: gaussian (SADABS; Bruker 2009)	k = −11→11
Tmin = 0.668, Tmax = 0.950	l = −22→22
19802 measured 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0622P)2 + 0.898P] where P = (Fo2 + 2Fc2)/3
2342 reflections	(Δ/σ)max < 0.001
95 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.39 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	0.82414 (4)	0.86402 (6)	0.46093 (3)	0.03532 (18)
O1	0.85676 (12)	1.0170 (2)	0.51708 (10)	0.0413 (4)
H1	0.823 (2)	1.114 (4)	0.504 (2)	0.062*
O2	0.71118 (12)	0.8030 (2)	0.47403 (10)	0.0456 (4)
C1	0.9197 (2)	0.7033 (2)	0.48579 (17)	0.0505 (5)
H1A	0.9154	0.6771	0.5444	0.076*
H1B	0.9907	0.7433	0.4727	0.076*
H1C	0.9044	0.6026	0.4537	0.076*
C11	0.84247 (18)	0.9303 (2)	0.35447 (12)	0.0384 (5)
C12	0.9378 (2)	1.0107 (2)	0.32936 (16)	0.0503 (5)
H12	0.9933	1.0267	0.3676	0.06*
C13	0.9496 (2)	1.0661 (4)	0.24804 (17)	0.0626 (7)
H13	1.0128	1.1201	0.2317	0.075*
C14	0.8681 (2)	1.0420 (4)	0.19095 (17)	0.0684 (8)
H14	0.8762	1.0804	0.1363	0.082*
C15	0.7754 (2)	0.9616 (4)	0.21438 (17)	0.0735 (9)
H15	0.7211	0.9447	0.1752	0.088*
C16	0.7612 (2)	0.9050 (2)	0.29563 (17)	0.0559 (7)
H16	0.6977	0.8504	0.3109	0.067*

	U11	U22	U33	U12	U13	U23
P1	0.0314 (2)	0.0321 (2)	0.0425 (2)	−0.0001 (2)	0.0008 (2)	0.0015 (2)
O1	0.0458 (9)	0.0356 (8)	0.0426 (9)	0.0015 (7)	−0.0052 (7)	0.0003 (7)
O2	0.0328 (8)	0.0381 (8)	0.0660 (11)	−0.0008 (7)	0.0059 (7)	0.0031 (7)
C1	0.0406 (13)	0.0406 (13)	0.0703 (16)	0.0049 (10)	−0.0013 (11)	0.0057 (11)
C11	0.0404 (11)	0.0356 (11)	0.0391 (11)	−0.0005 (9)	−0.0005 (9)	−0.0028 (9)
C12	0.0444 (13)	0.0555 (15)	0.0511 (14)	−0.0032 (11)	0.0031 (11)	0.0012 (11)
C13	0.0661 (18)	0.0662 (17)	0.0555 (16)	−0.0018 (15)	0.0193 (14)	0.0039 (14)
C14	0.100 (3)	0.0658 (18)	0.0395 (14)	0.0060 (18)	0.0101 (15)	0.0029 (13)
C15	0.095 (2)	0.078 (2)	0.0473 (16)	−0.007 (2)	−0.0204 (15)	−0.0019 (15)
C16	0.0537 (16)	0.0614 (16)	0.0525 (14)	−0.0097 (13)	−0.0108 (11)	−0.0034 (11)

P1—O2	1.4976 (16)	C12—C13	1.378 (4)
P1—O1	1.5526 (16)	C12—H12	0.93
P1—C1	1.777 (2)	C13—C14	1.375 (4)
P1—C11	1.794 (2)	C13—H13	0.93
O1—H1	0.89 (3)	C14—C15	1.366 (5)
C1—H1A	0.96	C14—H14	0.93
C1—H1B	0.96	C15—C16	1.383 (4)
C1—H1C	0.96	C15—H15	0.93
C11—C16	1.394 (3)	C16—H16	0.93
C11—C12	1.401 (3)
O2—P1—O1	114.29 (9)	C13—C12—C11	120.1 (2)
O2—P1—C1	111.56 (10)	C13—C12—H12	119.9
O1—P1—C1	104.21 (11)	C11—C12—H12	119.9
O2—P1—C11	110.13 (10)	C14—C13—C12	120.3 (3)
O1—P1—C11	106.92 (10)	C14—C13—H13	119.9
C1—P1—C11	109.45 (11)	C12—C13—H13	119.9
P1—O1—H1	114.(2)	C15—C14—C13	120.1 (3)
P1—C1—H1A	109.5	C15—C14—H14	119.9
P1—C1—H1B	109.5	C13—C14—H14	119.9
H1A—C1—H1B	109.5	C14—C15—C16	120.9 (3)
P1—C1—H1C	109.5	C14—C15—H15	119.6
H1A—C1—H1C	109.5	C16—C15—H15	119.6
H1B—C1—H1C	109.5	C15—C16—C11	119.7 (3)
C16—C11—C12	118.9 (2)	C15—C16—H16	120.2
C16—C11—P1	120.4 (2)	C11—C16—H16	120.2
C12—C11—P1	120.63 (17)
O2—P1—C11—C16	−6.3 (2)	P1—C11—C12—C13	−177.8 (2)
O1—P1—C11—C16	−131.0 (2)	C11—C12—C13—C14	−0.4 (4)
C1—P1—C11—C16	116.7 (2)	C12—C13—C14—C15	−0.5 (5)
O2—P1—C11—C12	172.62 (18)	C13—C14—C15—C16	0.7 (5)
O1—P1—C11—C12	47.9 (2)	C14—C15—C16—C11	0.0 (5)
C1—P1—C11—C12	−64.4 (2)	C12—C11—C16—C15	−0.9 (4)
C16—C11—C12—C13	1.1 (4)	P1—C11—C16—C15	178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.89 (3)	1.62 (3)	2.494 (2)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.89 (3)	1.62 (3)	2.494 (2)	168 (3)

Symmetry code: (i) .