Literature DB >> 21754171

Bis(3,5-dimeth-oxy-phen-yl)phosphinic acid.

Wei Cheng, Zhi-Qiang Feng, Jun-Mei Tang.

Abstract

In the crystal structure of the title compound, C(16)H(19)O(6)P, inter-molecular O-H⋯O inter-actions link the mol-ecules into chains parallel to the b axis. These chains are linked by C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.7307 (29) Å] into a three-dimensional network. The dihedral angle between the benzene rings is 73.5 (1)°. The C and O atoms of all four methoxy groups lie very close to the mean planes of their attached rings; the C atoms are 0.055 (2)-0.1038 (1) Å out of the mean plane of the attached rings.

Entities: Chemical Disease Gene

Year: 2011 PMID： 21754171 PMCID： PMC3099812 DOI： 10.1107/S1600536811008440

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For the synthesis of the title compound, see: Watson et al. (2006 ▶).

Experimental

Crystal data

C16H19O6P M = 338.28 Monoclinic, a = 14.554 (3) Å b = 7.7620 (16) Å c = 14.634 (3) Å β = 96.14 (3)° V = 1643.7 (6) Å3 Z = 4 Mo Kα radiation μ = 0.20 mm−1 T = 298 K 0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.944, T max = 0.981 3138 measured reflections 3014 independent reflections 2136 reflections with I > 2σ(I) R int = 0.032 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 0.162 S = 1.01 3014 reflections 208 parameters H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.32 e Å−3 Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008440/vm2080sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008440/vm2080Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₉O₆P	F(000) = 712
M_r = 338.28	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.554 (3) Å	θ = 10–14°
b = 7.7620 (16) Å	µ = 0.20 mm⁻¹
c = 14.634 (3) Å	T = 298 K
β = 96.14 (3)°	Block, colorless
V = 1643.7 (6) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2136 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
graphite	θ_max = 25.4°, θ_min = 1.9°
ω/2θ scans	h = 0→17
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.944, T_max = 0.981	l = −17→17
3138 measured reflections	3 standard reflections every 200 reflections
3014 independent reflections	intensity decay: 1%

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.095P)²] where P = (F_o² + 2F_c²)/3
3014 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.31 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	U_iso*/U_eq
P	0.84250 (5)	0.16050 (10)	0.25720 (5)	0.0347 (2)
O1	0.83620 (18)	−0.2020 (3)	0.55369 (14)	0.0568 (7)
C1	0.84208 (19)	−0.0319 (4)	0.41535 (19)	0.0369 (7)
H1A	0.8151	−0.1182	0.3774	0.044*
O2	0.96481 (18)	0.3582 (3)	0.57873 (15)	0.0582 (7)
C2	0.8584 (2)	−0.0570 (4)	0.5091 (2)	0.0388 (7)
O3	0.9727 (2)	−0.3021 (4)	0.0512 (2)	0.0853 (10)
C3	0.8993 (2)	0.0712 (4)	0.5657 (2)	0.0417 (7)
H3A	0.9099	0.0529	0.6287	0.050*
O4	1.17640 (19)	0.1274 (4)	0.1644 (2)	0.0833 (9)
C4	0.9241 (2)	0.2244 (4)	0.5293 (2)	0.0403 (7)
O5	0.85561 (14)	0.3545 (3)	0.23979 (14)	0.0429 (5)
H5A	0.8125	0.4084	0.2577	0.064*
C5	0.9083 (2)	0.2521 (4)	0.4345 (2)	0.0397 (7)
H5B	0.9256	0.3556	0.4093	0.048*
O6	0.74981 (14)	0.0893 (3)	0.22249 (13)	0.0432 (5)
C6	0.86672 (19)	0.1244 (4)	0.37875 (19)	0.0342 (7)
C7	0.9317 (2)	0.0648 (4)	0.19870 (19)	0.0388 (7)
C8	1.0195 (2)	0.1405 (4)	0.2072 (2)	0.0482 (8)
H8A	1.0313	0.2393	0.2424	0.058*
C9	1.0885 (2)	0.0655 (5)	0.1622 (2)	0.0570 (9)
C10	1.0691 (3)	−0.0832 (5)	0.1110 (3)	0.0669 (11)
H10A	1.1156	−0.1346	0.0816	0.080*
C11	0.9820 (3)	−0.1564 (5)	0.1027 (2)	0.0577 (9)
C12	0.9129 (2)	−0.0827 (4)	0.1475 (2)	0.0469 (8)
H12A	0.8544	−0.1320	0.1431	0.056*
C13	0.7992 (3)	−0.3423 (4)	0.5002 (2)	0.0583 (9)
H13A	0.7871	−0.4362	0.5399	0.087*
H13B	0.8426	−0.3782	0.4591	0.087*
H13C	0.7426	−0.3076	0.4653	0.087*
C14	0.9762 (3)	0.3417 (5)	0.6759 (2)	0.0683 (11)
H14A	1.0051	0.4436	0.7026	0.102*
H14B	1.0143	0.2434	0.6929	0.102*
H14C	0.9169	0.3269	0.6979	0.102*
C15	0.8843 (4)	−0.3867 (6)	0.0433 (3)	0.0889 (15)
H15A	0.8867	−0.4879	0.0059	0.133*
H15B	0.8379	−0.3097	0.0154	0.133*
H15C	0.8695	−0.4190	0.1033	0.133*
C16	1.1963 (3)	0.2843 (7)	0.2119 (4)	0.0937 (16)
H16A	1.2597	0.3150	0.2083	0.141*
H16B	1.1859	0.2707	0.2752	0.141*
H16C	1.1569	0.3736	0.1845	0.141*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0339 (4)	0.0366 (4)	0.0325 (4)	0.0010 (3)	−0.0014 (3)	0.0043 (3)
O1	0.0837 (18)	0.0470 (14)	0.0378 (12)	−0.0164 (12)	−0.0022 (11)	0.0083 (10)
C1	0.0355 (15)	0.0396 (16)	0.0347 (15)	−0.0025 (13)	−0.0010 (12)	−0.0011 (13)
O2	0.0813 (17)	0.0495 (14)	0.0405 (12)	−0.0168 (13)	−0.0085 (11)	−0.0039 (11)
C2	0.0410 (17)	0.0379 (17)	0.0370 (16)	−0.0002 (14)	0.0009 (13)	0.0034 (13)
O3	0.106 (2)	0.0688 (19)	0.088 (2)	−0.0052 (17)	0.0441 (18)	−0.0322 (16)
C3	0.0444 (17)	0.0488 (19)	0.0308 (15)	0.0022 (15)	−0.0016 (13)	0.0010 (14)
O4	0.0547 (16)	0.099 (2)	0.102 (2)	−0.0111 (16)	0.0322 (15)	−0.0187 (19)
C4	0.0409 (17)	0.0399 (17)	0.0384 (16)	−0.0004 (14)	−0.0039 (13)	−0.0040 (14)
O5	0.0405 (12)	0.0402 (12)	0.0480 (12)	0.0013 (10)	0.0044 (9)	0.0060 (10)
C5	0.0435 (17)	0.0362 (17)	0.0386 (16)	−0.0003 (14)	0.0014 (13)	0.0027 (14)
O6	0.0406 (12)	0.0478 (13)	0.0391 (11)	−0.0042 (10)	−0.0060 (9)	0.0079 (10)
C6	0.0290 (15)	0.0383 (16)	0.0345 (15)	0.0030 (12)	−0.0002 (12)	−0.0010 (13)
C7	0.0448 (18)	0.0412 (17)	0.0302 (15)	0.0056 (14)	0.0025 (13)	0.0041 (13)
C8	0.0483 (19)	0.054 (2)	0.0426 (17)	−0.0002 (16)	0.0067 (15)	−0.0035 (15)
C9	0.049 (2)	0.070 (2)	0.055 (2)	0.0012 (18)	0.0166 (16)	0.0011 (19)
C10	0.071 (3)	0.069 (3)	0.066 (2)	0.009 (2)	0.031 (2)	−0.004 (2)
C11	0.079 (3)	0.053 (2)	0.0446 (19)	0.003 (2)	0.0201 (18)	−0.0024 (17)
C12	0.052 (2)	0.0481 (19)	0.0411 (17)	0.0011 (16)	0.0081 (15)	0.0012 (16)
C13	0.077 (3)	0.047 (2)	0.051 (2)	−0.0154 (19)	0.0073 (18)	0.0025 (17)
C14	0.096 (3)	0.066 (3)	0.0411 (19)	−0.021 (2)	−0.0045 (19)	−0.0060 (19)
C15	0.118 (4)	0.065 (3)	0.086 (3)	−0.017 (3)	0.024 (3)	−0.025 (2)
C16	0.062 (3)	0.121 (4)	0.103 (4)	−0.027 (3)	0.030 (3)	−0.020 (3)

P—O6	1.496 (2)	C7—C12	1.379 (4)
P—O5	1.542 (2)	C7—C8	1.400 (4)
P—C7	1.791 (3)	C8—C9	1.387 (5)
P—C6	1.798 (3)	C8—H8A	0.9300
O1—C2	1.357 (4)	C9—C10	1.389 (5)
O1—C13	1.414 (4)	C10—C11	1.383 (5)
C1—C2	1.381 (4)	C10—H10A	0.9300
C1—C6	1.389 (4)	C11—C12	1.381 (5)
C1—H1A	0.9300	C12—H12A	0.9300
O2—C4	1.365 (4)	C13—H13A	0.9600
O2—C14	1.419 (4)	C13—H13B	0.9600
C2—C3	1.388 (4)	C13—H13C	0.9600
O3—C11	1.358 (4)	C14—H14A	0.9600
O3—C15	1.437 (5)	C14—H14B	0.9600
C3—C4	1.367 (4)	C14—H14C	0.9600
C3—H3A	0.9300	C15—H15A	0.9600
O4—C9	1.363 (4)	C15—H15B	0.9600
O4—C16	1.417 (5)	C15—H15C	0.9600
C4—C5	1.397 (4)	C16—H16A	0.9600
O5—H5A	0.8200	C16—H16B	0.9600
C5—C6	1.382 (4)	C16—H16C	0.9600
C5—H5B	0.9300

O6—P—O5	115.32 (12)	O4—C9—C10	116.3 (3)
O6—P—C7	110.96 (14)	C8—C9—C10	119.2 (3)
O5—P—C7	102.55 (13)	C11—C10—C9	121.4 (3)
O6—P—C6	110.65 (13)	C11—C10—H10A	119.3
O5—P—C6	107.51 (13)	C9—C10—H10A	119.3
C7—P—C6	109.45 (13)	O3—C11—C12	125.0 (4)
C2—O1—C13	117.9 (2)	O3—C11—C10	115.3 (3)
C2—C1—C6	118.9 (3)	C12—C11—C10	119.7 (3)
C2—C1—H1A	120.6	C7—C12—C11	119.3 (3)
C6—C1—H1A	120.6	C7—C12—H12A	120.3
C4—O2—C14	117.4 (3)	C11—C12—H12A	120.3
O1—C2—C1	124.8 (3)	O1—C13—H13A	109.5
O1—C2—C3	114.6 (3)	O1—C13—H13B	109.5
C1—C2—C3	120.6 (3)	H13A—C13—H13B	109.5
C11—O3—C15	117.4 (3)	O1—C13—H13C	109.5
C4—C3—C2	120.4 (3)	H13A—C13—H13C	109.5
C4—C3—H3A	119.8	H13B—C13—H13C	109.5
C2—C3—H3A	119.8	O2—C14—H14A	109.5
C9—O4—C16	117.2 (3)	O2—C14—H14B	109.5
O2—C4—C3	124.9 (3)	H14A—C14—H14B	109.5
O2—C4—C5	115.2 (3)	O2—C14—H14C	109.5
C3—C4—C5	119.9 (3)	H14A—C14—H14C	109.5
P—O5—H5A	109.5	H14B—C14—H14C	109.5
C6—C5—C4	119.4 (3)	O3—C15—H15A	109.5
C6—C5—H5B	120.3	O3—C15—H15B	109.5
C4—C5—H5B	120.3	H15A—C15—H15B	109.5
C5—C6—C1	120.9 (3)	O3—C15—H15C	109.5
C5—C6—P	120.0 (2)	H15A—C15—H15C	109.5
C1—C6—P	119.1 (2)	H15B—C15—H15C	109.5
C12—C7—C8	121.5 (3)	O4—C16—H16A	109.5
C12—C7—P	119.5 (2)	O4—C16—H16B	109.5
C8—C7—P	119.0 (2)	H16A—C16—H16B	109.5
C9—C8—C7	118.9 (3)	O4—C16—H16C	109.5
C9—C8—H8A	120.6	H16A—C16—H16C	109.5
C7—C8—H8A	120.6	H16B—C16—H16C	109.5
O4—C9—C8	124.5 (4)

C13—O1—C2—C1	4.3 (5)	O6—P—C7—C12	−14.6 (3)
C13—O1—C2—C3	−176.4 (3)	O5—P—C7—C12	−138.3 (2)
C6—C1—C2—O1	178.8 (3)	C6—P—C7—C12	107.8 (3)
C6—C1—C2—C3	−0.5 (4)	O6—P—C7—C8	166.3 (2)
O1—C2—C3—C4	−179.4 (3)	O5—P—C7—C8	42.6 (3)
C1—C2—C3—C4	0.0 (5)	C6—P—C7—C8	−71.3 (3)
C14—O2—C4—C3	−4.7 (5)	C12—C7—C8—C9	0.6 (5)
C14—O2—C4—C5	175.5 (3)	P—C7—C8—C9	179.7 (2)
C2—C3—C4—O2	−179.9 (3)	C16—O4—C9—C8	−3.7 (6)
C2—C3—C4—C5	−0.1 (5)	C16—O4—C9—C10	176.5 (4)
O2—C4—C5—C6	−179.5 (3)	C7—C8—C9—O4	179.5 (3)
C3—C4—C5—C6	0.7 (5)	C7—C8—C9—C10	−0.7 (5)
C4—C5—C6—C1	−1.2 (4)	O4—C9—C10—C11	−179.1 (4)
C4—C5—C6—P	178.0 (2)	C8—C9—C10—C11	1.0 (6)
C2—C1—C6—C5	1.1 (4)	C15—O3—C11—C12	−0.6 (6)
C2—C1—C6—P	−178.1 (2)	C15—O3—C11—C10	177.8 (4)
O6—P—C6—C5	−139.0 (2)	C9—C10—C11—O3	−179.6 (3)
O5—P—C6—C5	−12.2 (3)	C9—C10—C11—C12	−1.2 (6)
C7—P—C6—C5	98.4 (3)	C8—C7—C12—C11	−0.7 (5)
O6—P—C6—C1	40.2 (3)	P—C7—C12—C11	−179.8 (2)
O5—P—C6—C1	167.0 (2)	O3—C11—C12—C7	179.2 (3)
C7—P—C6—C1	−82.3 (2)	C10—C11—C12—C7	1.0 (5)

Cg2 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O6ⁱ	0.82	1.71	2.482 (3)	155
C14—H14B···Cg2ⁱⁱ	0.96	2.90	3.571 (4)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O6ⁱ	0.82	1.71	2.482 (3)	155
C14—H14B⋯Cg2ⁱⁱ	0.96	2.90	3.571 (4)	128

Symmetry codes: (i) ; (ii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination.

Authors: Donald A Watson; Melanie Chiu; Robert G Bergman
Journal: Organometallics Date: 2006-09-25 Impact factor: 3.876

2 in total