rac-Eth-yl(phen-yl)phosphinic acid.

The crystal structure of the title compound, C8H11O2P, features O-H⋯O hydrogen bonds, which link mol-ecules related by the b-glide plane into chains along [010].

Related literature

For background to metal-organic frameworks involving phospho­nate ligands, see: Gagnon et al. (2012 ▶). For details of coordination polymers constructed using phosphinic acids as the spacer ligand, see: Siqueira et al. (2006 ▶); Beckmann et al. (2009 ▶). For further details of phosphinic acids and the crystal structures of similar compounds, see: Burrow et al. (2000 ▶); Burrow & Siqueira da Silva (2011a ▶,b ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For geometry analysis using Mogul, see: Bruno et al. (2004 ▶).

Experimental

Crystal data

C8H11O2P

M = 170.14

Orthorhombic,

a = 13.5314 (16) Å

b = 8.0328 (9) Å

c = 15.922 (2) Å

V = 1730.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.41 × 0.12 × 0.11 mm

Data collection

Bruker X8 Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.906, T max = 0.971

14069 measured reflections

2650 independent reflections

1499 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.128

S = 1.09

2650 reflections

104 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); 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, 2012 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204812X/su2532sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204812X/su2532Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204812X/su2532Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204812X/su2532Isup4.cml

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

C8H11O2P	Dx = 1.306 Mg m−3
Mr = 170.14	Melting point = 336–341 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
a = 13.5314 (16) Å	Cell parameters from 2263 reflections
b = 8.0328 (9) Å	θ = 2.6–26.5°
c = 15.922 (2) Å	µ = 0.27 mm−1
V = 1730.6 (4) Å3	T = 296 K
Z = 8	Block, colourless
F(000) = 720	0.41 × 0.12 × 0.11 mm

Bruker X8 Kappa APEXII diffractometer	2650 independent reflections
Radiation source: sealed ceramic X ray tube, Siemens KFF	1499 reflections with I > 2σ(I)
Graphite crystal monochromator	Rint = 0.054
Detector resolution: 8.3333 pixels mm-1	θmax = 30.5°, θmin = 3.2°
0.5 ° ω & φ scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −9→11
Tmin = 0.906, Tmax = 0.971	l = −18→22
14069 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.0622P] where P = (Fo2 + 2Fc2)/3
2650 reflections	(Δ/σ)max < 0.001
104 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. Spectroscopic and TGA data for the title compound:IR: 1438 (m), 1177 (versus), 1137 (s), 998 (versus), 935 (versus), 745 (m), 718 (s), 692 (versus), 565 (m), 537 (m), 495 (m) cm-1. TGA: 483 - 603 K; 88% loss.

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 > 2σ(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	0.31872 (4)	0.19541 (6)	0.40958 (3)	0.03859 (18)
O1	0.34640 (11)	0.35269 (17)	0.35798 (8)	0.0468 (4)
H1	0.3212 (16)	0.444 (3)	0.3780 (15)	0.07*
O2	0.21554 (10)	0.13429 (17)	0.39751 (8)	0.0496 (4)
C11	0.40682 (16)	0.0441 (3)	0.37446 (13)	0.0539 (5)
H11A	0.4004	−0.0541	0.4095	0.065*
H11B	0.3897	0.012	0.3176	0.065*
C12	0.51433 (18)	0.0978 (3)	0.37521 (16)	0.0740 (7)
H12C	0.5222	0.1953	0.341	0.111*
H12A	0.5547	0.0096	0.3533	0.111*
H12B	0.5341	0.1224	0.4318	0.111*
C21	0.33743 (13)	0.2444 (2)	0.51841 (11)	0.0368 (4)
C22	0.41968 (14)	0.3314 (2)	0.54585 (13)	0.0474 (5)
H22	0.4675	0.3645	0.5073	0.057*
C23	0.43146 (16)	0.3697 (3)	0.62986 (14)	0.0584 (6)
H23	0.4868	0.4286	0.6476	0.07*
C24	0.36130 (17)	0.3207 (3)	0.68740 (14)	0.0579 (6)
H24	0.3694	0.3464	0.7439	0.069*
C25	0.28001 (17)	0.2344 (3)	0.66167 (13)	0.0576 (6)
H25	0.2329	0.2012	0.7008	0.069*
C26	0.26725 (15)	0.1960 (2)	0.57756 (12)	0.0466 (5)
H26	0.2115	0.1374	0.5605	0.056*

	U11	U22	U33	U12	U13	U23
P1	0.0484 (3)	0.0289 (3)	0.0386 (3)	0.0015 (2)	−0.0015 (2)	0.0000 (2)
O1	0.0652 (9)	0.0336 (8)	0.0416 (8)	0.0046 (7)	0.0087 (6)	0.0029 (6)
O2	0.0536 (8)	0.0376 (8)	0.0576 (9)	−0.0038 (7)	−0.0134 (7)	−0.0018 (6)
C11	0.0701 (13)	0.0399 (12)	0.0516 (12)	0.0116 (11)	0.0031 (10)	−0.0035 (9)
C12	0.0666 (15)	0.0666 (17)	0.0887 (19)	0.0219 (13)	0.0124 (13)	−0.0028 (14)
C21	0.0423 (10)	0.0295 (9)	0.0386 (9)	0.0002 (8)	0.0005 (7)	0.0011 (8)
C22	0.0479 (11)	0.0445 (12)	0.0498 (12)	−0.0086 (9)	−0.0002 (9)	−0.0006 (9)
C23	0.0613 (14)	0.0576 (14)	0.0563 (13)	−0.0077 (11)	−0.0151 (11)	−0.0097 (11)
C24	0.0732 (16)	0.0599 (15)	0.0405 (11)	0.0076 (12)	−0.0076 (11)	−0.0081 (10)
C25	0.0620 (14)	0.0667 (15)	0.0442 (12)	0.0032 (11)	0.0132 (10)	0.0001 (11)
C26	0.0444 (11)	0.0458 (12)	0.0496 (12)	−0.0047 (9)	0.0028 (8)	−0.0014 (9)

P1—O2	1.4925 (14)	C21—C22	1.385 (2)
P1—O1	1.5529 (14)	C21—C26	1.393 (3)
P1—C11	1.792 (2)	C22—C23	1.382 (3)
P1—C21	1.7950 (19)	C22—H22	0.93
O1—H1	0.87 (2)	C23—C24	1.377 (3)
C11—C12	1.517 (3)	C23—H23	0.93
C11—H11A	0.97	C24—C25	1.363 (3)
C11—H11B	0.97	C24—H24	0.93
C12—H12C	0.96	C25—C26	1.385 (3)
C12—H12A	0.96	C25—H25	0.93
C12—H12B	0.96	C26—H26	0.93
O2—P1—O1	115.16 (8)	C22—C21—C26	118.40 (18)
O2—P1—C11	111.05 (10)	C22—C21—P1	121.91 (14)
O1—P1—C11	103.08 (9)	C26—C21—P1	119.69 (14)
O2—P1—C21	109.17 (8)	C23—C22—C21	120.68 (19)
O1—P1—C21	107.36 (8)	C23—C22—H22	119.7
C11—P1—C21	110.87 (9)	C21—C22—H22	119.7
P1—O1—H1	113.5 (16)	C24—C23—C22	120.06 (19)
C12—C11—P1	116.28 (16)	C24—C23—H23	120.0
C12—C11—H11A	108.2	C22—C23—H23	120.0
P1—C11—H11A	108.2	C25—C24—C23	120.1 (2)
C12—C11—H11B	108.2	C25—C24—H24	119.9
P1—C11—H11B	108.2	C23—C24—H24	119.9
H11A—C11—H11B	107.4	C24—C25—C26	120.3 (2)
C11—C12—H12C	109.5	C24—C25—H25	119.8
C11—C12—H12A	109.5	C26—C25—H25	119.8
H12C—C12—H12A	109.5	C25—C26—C21	120.43 (19)
C11—C12—H12B	109.5	C25—C26—H26	119.8
H12C—C12—H12B	109.5	C21—C26—H26	119.8
H12A—C12—H12B	109.5
O2—P1—C11—C12	174.11 (16)	C26—C21—C22—C23	−0.3 (3)
O1—P1—C11—C12	50.26 (18)	P1—C21—C22—C23	179.01 (16)
C21—P1—C11—C12	−64.34 (19)	C21—C22—C23—C24	0.3 (3)
O2—P1—C21—C22	−168.19 (15)	C22—C23—C24—C25	−0.1 (3)
O1—P1—C21—C22	−42.73 (17)	C23—C24—C25—C26	−0.2 (3)
C11—P1—C21—C22	69.16 (18)	C24—C25—C26—C21	0.2 (3)
O2—P1—C21—C26	11.07 (18)	C22—C21—C26—C25	0.0 (3)
O1—P1—C21—C26	136.53 (16)	P1—C21—C26—C25	−179.28 (15)
C11—P1—C21—C26	−111.58 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.87 (2)	1.64 (2)	2.4931 (19)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.87 (2)	1.64 (2)	2.4931 (19)	168 (2)

Symmetry code: (i) .