Cyclo­hexyl­ammonium 2'-hydroxy-2-biphenyl phosphonate

In the molecular structure of the title compound, C₆H₁₄N⁺·C₁₂H₁₀O₄P^-, three O atoms are bonded to phospho­rus. The oxy­gen connected to the bi­phenoxy residue is not involved in hydrogen bonding; of the other two, one oxy­gen is involved in intermolecular hydrogen bonding to an N-H group as well as the O-H group of the bi­phenoxy residue, while the second oxy­gen is involved in hydrogen bonding to two N-H groups.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: Structure Determination Package (Frenz, 1985); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX6a (McArdle, 1995); software used to prepare material for publication: SHELXL97.

Cyclohexylammonium (2-oxy-2'-hydroxy-biphenyl)phosphonate

Crystal data

C6H11NH3^+·C12H10O4P^−	Dx = 1.293 Mg m^−3
Mr = 349.35	Melting point: 453 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 30.992 (7) Å	θ = 9.5–12.0°
b = 8.613 (4) Å	µ = 0.17 mm^−1
c = 6.721 (7) Å	T = 293 K
V = 1794 (2) Å^3	Needles, colourless
Z = 4	0.30 × 0.20 × 0.20 mm
F(000) = 744

Data collection

Enraf-Nonius CAD 4 diffractometer	Rint = 0.006
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.4°
Graphite monochromator	h = 0→36
Profile data from ω scans	k = 0→10
1706 measured reflections	l = 0→7
1705 independent reflections	3 standard reflections every 90 min
1309 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.177	Calculated w = 1/[σ^2(Fo^2) + (0.0925P)^2 + 1.9P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
1705 reflections	Δρmax = 0.39 e Å^−3
226 parameters	Δρmin = −0.34 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P	0.08666 (5)	0.09910 (19)	−0.0075 (2)	0.0347 (4)
O1	0.09107 (15)	0.0695 (6)	0.2088 (7)	0.0446 (13)
O2	0.04362 (15)	0.0982 (6)	−0.1006 (8)	0.0494 (13)
O3	0.11314 (14)	−0.0261 (5)	−0.1318 (7)	0.0421 (11)
O4	0.15371 (18)	0.0225 (6)	−0.5150 (8)	0.0505 (13)
N	0.45837 (17)	0.9382 (6)	0.0164 (9)	0.0420 (13)
HA	0.4860	0.9315	−0.0185	0.063*
HB	0.4563	0.9836	0.1350	0.063*
HC	0.4441	0.9942	−0.0734	0.063*
C1	0.1538 (2)	−0.0808 (8)	−0.0790 (10)	0.0377 (15)
C2	0.1571 (3)	−0.2171 (9)	0.0206 (12)	0.0546 (19)
H2	0.1323	−0.2717	0.0554	0.065*
C3	0.1977 (4)	−0.2760 (11)	0.0712 (13)	0.071 (3)
H3	0.2002	−0.3712	0.1355	0.085*
C4	0.2330 (3)	−0.1931 (10)	0.0256 (12)	0.064 (2)
H4	0.2600	−0.2298	0.0635	0.077*
C5	0.2302 (2)	−0.0572 (10)	−0.0745 (11)	0.052 (2)
H5	0.2553	−0.0037	−0.1061	0.062*
C6	0.1903 (2)	0.0050 (8)	−0.1317 (10)	0.0396 (15)
C7	0.1884 (2)	0.1496 (9)	−0.2489 (10)	0.0390 (15)
C8	0.1700 (2)	0.1562 (9)	−0.4379 (10)	0.0425 (17)
C9	0.1692 (2)	0.2944 (9)	−0.5413 (13)	0.056 (2)
H9	0.1562	0.2985	−0.6658	0.068*
C10	0.1872 (3)	0.4248 (10)	−0.4635 (16)	0.068 (3)
H10	0.1861	0.5175	−0.5342	0.082*
C11	0.2072 (3)	0.4204 (10)	−0.2812 (16)	0.065 (2)
H11	0.2204	0.5084	−0.2295	0.078*
C12	0.2071 (3)	0.2838 (10)	−0.1769 (12)	0.056 (2)
H12	0.2202	0.2814	−0.0525	0.068*
C13	0.4562 (3)	0.6910 (9)	0.2048 (11)	0.051 (2)
H13A	0.4497	0.7478	0.3256	0.061*
H13B	0.4873	0.6807	0.1949	0.061*
C14	0.4357 (3)	0.5309 (11)	0.2137 (14)	0.062 (2)
H14A	0.4047	0.5413	0.2316	0.075*
H14B	0.4471	0.4740	0.3265	0.075*
C15	0.4449 (3)	0.4409 (9)	0.0208 (15)	0.063 (2)
H15A	0.4757	0.4215	0.0101	0.076*
H15B	0.4303	0.3413	0.0252	0.076*
C16	0.4299 (3)	0.5305 (10)	−0.1588 (14)	0.060 (2)
H16A	0.3987	0.5381	−0.1567	0.072*
H16B	0.4381	0.4751	−0.2786	0.072*
C17	0.4491 (3)	0.6919 (9)	−0.1634 (11)	0.051 (2)
H17A	0.4375	0.7487	−0.2758	0.061*
H17B	0.4801	0.6844	−0.1806	0.061*
C18	0.4393 (2)	0.7791 (7)	0.0268 (10)	0.0382 (15)
H18	0.4080	0.7889	0.0398	0.046*
H1	0.1094 (16)	0.224 (6)	−0.045 (9)	0.021 (14)*
HO4	0.136 (4)	0.034 (14)	−0.59 (2)	0.11 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P	0.0399 (8)	0.0427 (8)	0.0213 (8)	−0.0006 (7)	0.0000 (8)	0.0031 (9)
O1	0.056 (3)	0.067 (3)	0.010 (2)	0.002 (2)	0.000 (2)	0.001 (2)
O2	0.043 (3)	0.074 (3)	0.032 (3)	0.009 (2)	−0.003 (2)	0.000 (3)
O3	0.040 (2)	0.057 (3)	0.029 (2)	0.004 (2)	−0.003 (2)	−0.005 (2)
O4	0.064 (3)	0.061 (3)	0.027 (3)	−0.004 (3)	−0.017 (3)	−0.004 (3)
N	0.049 (3)	0.055 (3)	0.022 (3)	0.001 (2)	0.001 (3)	−0.001 (3)
C1	0.047 (4)	0.045 (4)	0.021 (3)	0.006 (3)	−0.002 (3)	−0.007 (3)
C2	0.070 (5)	0.059 (4)	0.034 (4)	0.008 (4)	0.006 (4)	0.008 (4)
C3	0.117 (8)	0.066 (5)	0.030 (5)	0.033 (6)	−0.003 (5)	0.005 (4)
C4	0.080 (6)	0.083 (6)	0.028 (4)	0.032 (5)	−0.019 (4)	−0.006 (4)
C5	0.042 (4)	0.081 (5)	0.032 (4)	0.008 (4)	−0.009 (3)	−0.015 (4)
C6	0.048 (4)	0.053 (4)	0.018 (3)	0.006 (3)	−0.005 (3)	−0.009 (3)
C7	0.035 (3)	0.056 (4)	0.026 (3)	−0.002 (3)	0.000 (3)	−0.005 (3)
C8	0.047 (4)	0.051 (4)	0.030 (4)	−0.007 (3)	−0.002 (3)	−0.001 (3)
C9	0.062 (5)	0.064 (5)	0.043 (5)	−0.003 (4)	0.000 (4)	0.011 (4)
C10	0.075 (5)	0.063 (5)	0.067 (7)	−0.011 (4)	0.011 (5)	0.012 (5)
C11	0.064 (5)	0.064 (5)	0.066 (6)	−0.019 (4)	0.009 (5)	−0.011 (5)
C12	0.063 (5)	0.072 (5)	0.034 (4)	−0.017 (4)	−0.003 (4)	−0.008 (4)
C13	0.072 (6)	0.060 (5)	0.022 (4)	0.012 (4)	0.002 (4)	0.004 (4)
C14	0.079 (6)	0.069 (5)	0.040 (4)	0.011 (5)	0.007 (4)	0.012 (4)
C15	0.081 (5)	0.053 (4)	0.056 (5)	0.005 (4)	0.001 (5)	0.003 (5)
C16	0.079 (6)	0.060 (5)	0.041 (4)	−0.009 (5)	−0.011 (4)	−0.002 (4)
C17	0.068 (5)	0.063 (5)	0.021 (4)	−0.001 (4)	−0.005 (3)	−0.001 (4)
C18	0.039 (3)	0.044 (3)	0.031 (4)	0.000 (3)	0.006 (3)	0.002 (3)

Geometric parameters (Å, º)

P—H1	1.31 (5)	C6—C7	1.475 (10)
P—O2	1.473 (5)	C7—C12	1.380 (10)
P—O1	1.482 (5)	C7—C8	1.394 (10)
P—O3	1.592 (5)	C8—C9	1.379 (11)
O3—C1	1.390 (8)	C9—C10	1.359 (12)
O4—C8	1.359 (9)	C10—C11	1.373 (14)
N—C18	1.493 (8)	C11—C12	1.369 (12)
C1—C2	1.356 (10)	C13—C18	1.510 (10)
C1—C6	1.399 (10)	C13—C14	1.520 (13)
C2—C3	1.399 (12)	C14—C15	1.538 (13)
C3—C4	1.342 (12)	C15—C16	1.507 (13)
C4—C5	1.353 (11)	C16—C17	1.513 (12)
C5—C6	1.400 (10)	C17—C18	1.513 (10)
H1—P—O2	114 (2)	C12—C7—C6	120.2 (6)
H1—P—O1	106 (3)	C8—C7—C6	122.5 (6)
O2—P—O1	119.9 (3)	O4—C8—C9	122.2 (6)
H1—P—O3	100 (2)	O4—C8—C7	117.7 (7)
O2—P—O3	103.9 (3)	C9—C8—C7	120.1 (7)
O1—P—O3	110.5 (3)	C10—C9—C8	120.8 (8)
C1—O3—P	124.2 (4)	C9—C10—C11	120.4 (9)
C2—C1—O3	119.3 (7)	C12—C11—C10	118.7 (8)
C2—C1—C6	121.3 (6)	C11—C12—C7	122.7 (8)
O3—C1—C6	119.4 (6)	C18—C13—C14	110.0 (7)
C1—C2—C3	120.2 (8)	C13—C14—C15	110.2 (7)
C4—C3—C2	119.0 (8)	C16—C15—C14	111.1 (6)
C3—C4—C5	121.4 (8)	C15—C16—C17	111.4 (7)
C4—C5—C6	121.7 (8)	C16—C17—C18	111.1 (7)
C1—C6—C5	116.3 (7)	N—C18—C13	111.2 (6)
C1—C6—C7	123.3 (6)	N—C18—C17	109.7 (6)
C5—C6—C7	120.3 (7)	C13—C18—C17	110.5 (5)
C12—C7—C8	117.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—HC···O1^i	0.89	1.94	2.811 (8)	167
N—HB···O2^ii	0.89	2.03	2.920 (8)	175
N—HA···O2^iii	0.89	1.89	2.775 (7)	176
O4—HO4···O1^iv	0.74 (13)	1.98 (13)	2.717 (7)	175 (15)

Symmetry codes: (i) −x+1/2, y+1, z−1/2; (ii) −x+1/2, y+1, z+1/2; (iii) x+1/2, −y+1, z; (iv) x, y, z−1.