Benz-yl(phen-yl)phosphinic acid.

The title compound, C(13)H(13)O(2)P, crystallized as enanti-omerically pure crystals; for the crystal measured, the P atom has R stereochemistry. The crystal structure displays O-H⋯O hydrogen bonding, which links individual mol-ecules related by a 2(1) screw axis parallel to the crystallographic a-axis direction into continuous chains.

Related literature

For background to phosphinic acids, see: Beckmann et al. (2009 ▶); Burrow et al. (2000 ▶); Chen & Suslick (1993 ▶); Siqueira et al. (2006 ▶); Vioux et al. (2004 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). Geom­etrical analysis was performed with Mogul (Bruno et al., 2004 ▶).

Experimental

Crystal data

C13H13O2P

M = 232.20

Orthorhombic,

a = 5.7326 (2) Å

b = 12.3430 (3) Å

c = 16.7794 (4) Å

V = 1187.27 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.65 × 0.34 × 0.22 mm

Data collection

Bruker X8 Kappa APEXII diffractometer

Absorption correction: gaussian (SADABS; Bruker, 2009 ▶) T min = 0.880, T max = 0.964

14337 measured reflections

3451 independent reflections

3119 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.05

3451 reflections

148 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1447 Friedel pairs

Flack parameter: 0.00 (11)

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008245/zb2011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008245/zb2011Isup2.hkl

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

C13H13O2P	Dx = 1.299 Mg m−3
Mr = 232.20	Melting point = 454–456 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4929 reflections
a = 5.7326 (2) Å	θ = 3.3–28.0°
b = 12.3430 (3) Å	µ = 0.21 mm−1
c = 16.7794 (4) Å	T = 295 K
V = 1187.27 (6) Å3	Block, colourless
Z = 4	0.65 × 0.34 × 0.22 mm
F(000) = 488

Bruker X8 Kappa APEXII diffractometer	3451 independent reflections
Radiation source: fine-focus sealed tube	3119 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 0.0833 pixels mm-1	θmax = 30.0°, θmin = 3.5°
φ and ω scans	h = −8→8
Absorption correction: gaussian (SADABS; Bruker, 2009)	k = −17→17
Tmin = 0.880, Tmax = 0.964	l = −20→23
14337 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.2054P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3451 reflections	Δρmax = 0.47 e Å−3
148 parameters	Δρmin = −0.23 e Å−3
0 restraints	Absolute structure: Flack & Bernardinelli (2000), 1447 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (11)

Experimental. SADABS (Bruker, 2009) was used to perform the numeric absorption correction based on the crystal dimensions determined by face indexing.The number of Friedel pairs measured is 1447. The crystal was not cut to size as it tended to fracture.

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
C11	0.0173 (3)	0.51865 (12)	0.54568 (9)	0.0333 (3)
C12	0.2219 (4)	0.53887 (16)	0.58763 (12)	0.0445 (4)
H12	0.3342	0.4849	0.5926	0.053*
C13	0.2585 (4)	0.64005 (18)	0.62216 (13)	0.0530 (5)
H13	0.3935	0.6530	0.6513	0.064*
C14	0.0955 (4)	0.72087 (17)	0.61322 (14)	0.0539 (5)
H14	0.1215	0.7886	0.6359	0.065*
C15	−0.1073 (4)	0.70186 (17)	0.57065 (15)	0.0539 (5)
H15	−0.2170	0.7567	0.5646	0.065*
C16	−0.1464 (3)	0.60086 (15)	0.53698 (12)	0.0428 (4)
H16	−0.2828	0.5881	0.5085	0.051*
C21	0.1121 (4)	0.37609 (16)	0.41002 (11)	0.0463 (4)
H21A	0.2768	0.3904	0.4181	0.056*
H21B	0.0971	0.3022	0.3910	0.056*
C22	0.0212 (3)	0.45208 (15)	0.34658 (10)	0.0400 (4)
C23	0.1432 (5)	0.54488 (18)	0.32764 (13)	0.0561 (5)
H23	0.2820	0.5606	0.3539	0.067*
C24	0.0593 (6)	0.6153 (2)	0.26926 (16)	0.0756 (8)
H24	0.1425	0.6777	0.2566	0.091*
C25	−0.1438 (6)	0.5929 (3)	0.23093 (16)	0.0769 (9)
H25	−0.2001	0.6403	0.1924	0.092*
C26	−0.2657 (6)	0.5010 (3)	0.24868 (14)	0.0720 (7)
H26	−0.4033	0.4855	0.2216	0.086*
C27	−0.1855 (4)	0.4311 (2)	0.30663 (12)	0.0535 (5)
H27	−0.2709	0.3693	0.3190	0.064*
H1	0.101 (5)	0.234 (3)	0.5458 (19)	0.080*
O1	0.0790 (3)	0.30554 (11)	0.56144 (9)	0.0480 (3)
O2	−0.2947 (2)	0.37242 (9)	0.49255 (9)	0.0444 (3)
P1	−0.03542 (8)	0.38743 (3)	0.50410 (3)	0.03482 (11)

	U11	U22	U33	U12	U13	U23
C11	0.0375 (8)	0.0272 (6)	0.0350 (7)	−0.0003 (6)	0.0014 (6)	−0.0005 (5)
C12	0.0399 (9)	0.0415 (9)	0.0520 (10)	0.0028 (8)	−0.0048 (8)	−0.0043 (8)
C13	0.0490 (11)	0.0526 (11)	0.0574 (11)	−0.0089 (9)	−0.0107 (9)	−0.0098 (9)
C14	0.0639 (14)	0.0378 (9)	0.0600 (12)	−0.0056 (9)	−0.0009 (10)	−0.0138 (9)
C15	0.0590 (13)	0.0342 (9)	0.0684 (13)	0.0105 (9)	−0.0095 (10)	−0.0101 (9)
C16	0.0420 (9)	0.0341 (8)	0.0525 (10)	0.0031 (7)	−0.0078 (8)	−0.0058 (7)
C21	0.0504 (10)	0.0418 (9)	0.0465 (9)	0.0155 (8)	0.0003 (8)	−0.0070 (8)
C22	0.0468 (10)	0.0405 (8)	0.0327 (7)	0.0060 (7)	0.0035 (7)	−0.0051 (6)
C23	0.0652 (14)	0.0509 (11)	0.0523 (11)	−0.0075 (10)	0.0080 (10)	−0.0044 (9)
C24	0.111 (2)	0.0522 (13)	0.0638 (14)	−0.0030 (16)	0.0222 (15)	0.0105 (12)
C25	0.109 (2)	0.0749 (18)	0.0464 (12)	0.0311 (18)	0.0081 (14)	0.0147 (12)
C26	0.0729 (15)	0.103 (2)	0.0404 (10)	0.0214 (15)	−0.0098 (11)	−0.0021 (12)
C27	0.0559 (12)	0.0641 (13)	0.0405 (10)	−0.0047 (10)	−0.0024 (9)	−0.0037 (9)
O1	0.0649 (10)	0.0328 (6)	0.0461 (7)	0.0112 (6)	−0.0006 (6)	0.0035 (5)
O2	0.0413 (6)	0.0326 (5)	0.0592 (8)	−0.0041 (5)	0.0011 (6)	−0.0015 (6)
P1	0.0409 (2)	0.02614 (17)	0.03746 (19)	0.00195 (14)	0.00110 (17)	−0.00116 (16)

C11—C16	1.390 (2)	C21—H21B	0.9700
C11—C12	1.391 (3)	C22—C23	1.379 (3)
C11—P1	1.7893 (16)	C22—C27	1.386 (3)
C12—C13	1.393 (3)	C23—C24	1.395 (4)
C12—H12	0.9300	C23—H23	0.9300
C13—C14	1.375 (3)	C24—C25	1.359 (5)
C13—H13	0.9300	C24—H24	0.9300
C14—C15	1.384 (3)	C25—C26	1.365 (5)
C14—H14	0.9300	C25—H25	0.9300
C15—C16	1.387 (3)	C26—C27	1.379 (4)
C15—H15	0.9300	C26—H26	0.9300
C16—H16	0.9300	C27—H27	0.9300
C21—C22	1.511 (3)	O1—P1	1.5420 (14)
C21—P1	1.7962 (19)	O1—H1	0.93 (3)
C21—H21A	0.9700	O2—P1	1.5104 (13)
C16—C11—C12	119.46 (16)	C23—C22—C21	120.2 (2)
C16—C11—P1	120.38 (13)	C27—C22—C21	121.29 (19)
C12—C11—P1	120.15 (13)	C22—C23—C24	120.3 (3)
C11—C12—C13	119.89 (18)	C22—C23—H23	119.9
C11—C12—H12	120.1	C24—C23—H23	119.9
C13—C12—H12	120.1	C25—C24—C23	120.0 (3)
C14—C13—C12	120.20 (19)	C25—C24—H24	120.0
C14—C13—H13	119.9	C23—C24—H24	120.0
C12—C13—H13	119.9	C24—C25—C26	120.3 (2)
C13—C14—C15	120.26 (18)	C24—C25—H25	119.8
C13—C14—H14	119.9	C26—C25—H25	119.8
C15—C14—H14	119.9	C25—C26—C27	120.2 (3)
C14—C15—C16	119.90 (19)	C25—C26—H26	119.9
C14—C15—H15	120.0	C27—C26—H26	119.9
C16—C15—H15	120.0	C26—C27—C22	120.6 (2)
C15—C16—C11	120.27 (18)	C26—C27—H27	119.7
C15—C16—H16	119.9	C22—C27—H27	119.7
C11—C16—H16	119.9	P1—O1—H1	120 (2)
C22—C21—P1	114.11 (12)	O2—P1—O1	114.73 (8)
C22—C21—H21A	108.7	O2—P1—C11	109.11 (8)
P1—C21—H21A	108.7	O1—P1—C11	106.16 (8)
C22—C21—H21B	108.7	O2—P1—C21	109.93 (9)
P1—C21—H21B	108.7	O1—P1—C21	107.28 (8)
H21A—C21—H21B	107.6	C11—P1—C21	109.49 (9)
C23—C22—C27	118.5 (2)
C16—C11—C12—C13	1.6 (3)	C24—C25—C26—C27	1.1 (4)
P1—C11—C12—C13	−177.83 (16)	C25—C26—C27—C22	−1.1 (4)
C11—C12—C13—C14	−1.6 (3)	C23—C22—C27—C26	0.7 (3)
C12—C13—C14—C15	0.7 (4)	C21—C22—C27—C26	−179.8 (2)
C13—C14—C15—C16	0.1 (4)	C16—C11—P1—O2	−22.31 (17)
C14—C15—C16—C11	−0.1 (3)	C12—C11—P1—O2	157.10 (14)
C12—C11—C16—C15	−0.7 (3)	C16—C11—P1—O1	−146.45 (15)
P1—C11—C16—C15	178.69 (17)	C12—C11—P1—O1	32.96 (17)
P1—C21—C22—C23	102.5 (2)	C16—C11—P1—C21	98.04 (16)
P1—C21—C22—C27	−77.0 (2)	C12—C11—P1—C21	−82.55 (16)
C27—C22—C23—C24	−0.2 (3)	C22—C21—P1—O2	54.98 (17)
C21—C22—C23—C24	−179.8 (2)	C22—C21—P1—O1	−179.66 (14)
C22—C23—C24—C25	0.2 (4)	C22—C21—P1—C11	−64.87 (17)
C23—C24—C25—C26	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.93 (3)	1.58 (3)	2.4838 (18)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.93 (3)	1.58 (3)	2.4838 (18)	163 (3)

Symmetry code: (i) .