4-(Diphenyl­phosphino­yl)benzoic acid

Li, Y.-J.; Zhang, R.-C.

doi:10.1107/S1600536808031449

organic compounds

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Volume 64| Part 11| November 2008| Page o2074

doi:10.1107/S1600536808031449

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4-(Diphenylphosphinoyl)benzoic acid

Yuan-Jing Li ^a ^* and Rong-Chang Zhang ^a

^aFaculty of Chemistry and Biology, Beihua University, Jilin City 132013, People's Republic of China
^*Correspondence e-mail: jls_yjl@126.com

(Received 29 September 2008; accepted 29 September 2008; online 4 October 2008)

Molecules of the title compound, C₁₉H₁₅O₃P, are connected by O—H⋯O hydrogen bonds between the carboxylic acid OH group and the phosphinoyl O atom, forming chains running along the crystallographic b axis.

Related literature

For general background, see, see: Al-Farhan (1992 ). For related structures, see: Etter (1990 ); Fuquen & Lechat (1992 ).

Experimental

Crystal data

C₁₉H₁₅O₃P
M_r = 322.28
Monoclinic, C 2/c
a = 18.018 (3) Å
b = 10.0921 (18) Å
c = 18.028 (4) Å
β = 91.467 (4)°
V = 3277.1 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 (2) K
0.24 × 0.21 × 0.17 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SAINT; Bruker, 1998 ) T_min = 0.956, T_max = 0.971
8975 measured reflections
3228 independent reflections
1796 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.110
S = 0.91
3228 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ⁱ	0.82	1.78	2.579 (3)	163
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031449/bt2800sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031449/bt2800Isup2.hkl

checkCIF report

Comment top

Triphenylphosphine is an important intermediate in organic chemistry. So far, its derivative, triphenylphosphine P-oxide with diverse hydrogen-bond donors, have been extensively studied (Al-Farhan, 1992). However, 4-(triphenylphosphine oxide)formic acid, as an important derivative of triphenylphosphine has been rarely studied (Fuquen & Lechat, 1992). The title compound was synthesized from 4-(diphenylphosphino)benzoic acid.

The O—H···O hydrogen bonds between the O atoms of the oxide group and the carboxylate group link the molecules to chains running along the crystallographic b axis.

Related literature top

For related literature, see: Al-Farhan (1992); Etter (1990); Fuquen & Lechat (1992). [From the Section Editors: It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···." etc. Please revise this section as indicated.]

Experimental top

4-(Diphenylphosphino)benzoic acid (5 mmol) and hydrogen peroxide (0.5 ml) were dissolved in a mixture of CH₃CH₂OH and water solution (40 ml) (CH₃CH₂OH: water = 3:1). The mixture was refluxed for 1 h, after cooling, this mixture was diluted with water, immediately resulting in a white precipitate, which was washed with water. Crystals of the title compound were obtained by recrystallization from CH₃CH₂OH.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. View of the chain structure of the title compound; hydrogen-bonds are drawn as dashed lines.

4-(Diphenylphosphinoyl)benzoic acid top

Crystal data top

C₁₉H₁₅O₃P	F(000) = 1344
M_r = 322.28	D_x = 1.306 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3228 reflections
a = 18.018 (3) Å	θ = 1.1–26.0°
b = 10.0921 (18) Å	µ = 0.18 mm⁻¹
c = 18.028 (4) Å	T = 293 K
β = 91.467 (4)°	Block, white
V = 3277.1 (11) Å³	0.24 × 0.21 × 0.17 mm
Z = 8

Data collection top

Bruker APEX CCD area-detector diffractometer	3228 independent reflections
Radiation source: fine-focus sealed tube	1796 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SAINT; Bruker, 1998)	h = −22→16
T_min = 0.956, T_max = 0.971	k = −11→12
8975 measured reflections	l = −21→22

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0279P)²] where P = (F_o² + 2F_c²)/3
3228 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₁₅O₃P	V = 3277.1 (11) Å³
M_r = 322.28	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.018 (3) Å	µ = 0.18 mm⁻¹
b = 10.0921 (18) Å	T = 293 K
c = 18.028 (4) Å	0.24 × 0.21 × 0.17 mm
β = 91.467 (4)°

Data collection top

Bruker APEX CCD area-detector diffractometer	3228 independent reflections
Absorption correction: multi-scan (SAINT; Bruker, 1998)	1796 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.971	R_int = 0.079
8975 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 0.91	Δρ_max = 0.38 e Å⁻³
3228 reflections	Δρ_min = −0.25 e Å⁻³
208 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.10622 (15)	−0.1711 (3)	0.17928 (17)	0.0272 (7)
C2	0.07579 (16)	−0.2100 (3)	0.11102 (17)	0.0346 (8)
H2	0.0682	−0.1471	0.0738	0.041*
C3	0.05660 (16)	−0.3408 (3)	0.09760 (17)	0.0332 (8)
H3A	0.0367	−0.3658	0.0516	0.040*
C4	0.06720 (16)	−0.4344 (3)	0.15324 (17)	0.0283 (8)
C5	0.09413 (17)	−0.3952 (3)	0.22220 (17)	0.0353 (9)
H5	0.0994	−0.4572	0.2601	0.042*
C6	0.11340 (16)	−0.2644 (3)	0.23532 (17)	0.0330 (8)
H6	0.1313	−0.2390	0.2820	0.040*
C7	0.05236 (17)	−0.5773 (3)	0.13561 (19)	0.0342 (8)
C8	0.22186 (16)	0.0143 (3)	0.14358 (16)	0.0304 (8)
C9	0.27202 (18)	−0.0893 (3)	0.13654 (18)	0.0401 (9)
H9	0.2615	−0.1718	0.1566	0.048*
C10	0.33799 (19)	−0.0698 (4)	0.0995 (2)	0.0466 (10)
H10	0.3713	−0.1396	0.0951	0.056*
C11	0.35436 (19)	0.0512 (4)	0.06954 (18)	0.0453 (10)
H11	0.3986	0.0633	0.0449	0.054*
C12	0.30524 (19)	0.1546 (4)	0.07603 (19)	0.0463 (10)
H12	0.3161	0.2369	0.0558	0.056*
C13	0.23927 (18)	0.1359 (3)	0.11296 (18)	0.0395 (9)
H13	0.2063	0.2062	0.1172	0.047*
C14	0.15618 (17)	0.0219 (3)	0.28792 (17)	0.0307 (8)
C15	0.22564 (17)	0.0031 (3)	0.32047 (18)	0.0384 (8)
H15	0.2650	−0.0225	0.2914	0.046*
C16	0.2371 (2)	0.0220 (3)	0.3956 (2)	0.0473 (10)
H16	0.2843	0.0106	0.4168	0.057*
C17	0.1788 (2)	0.0578 (3)	0.4395 (2)	0.0516 (10)
H17	0.1864	0.0706	0.4902	0.062*
C18	0.1090 (2)	0.0743 (4)	0.4076 (2)	0.0597 (11)
H18	0.0692	0.0969	0.4370	0.072*
C19	0.09794 (19)	0.0576 (3)	0.3324 (2)	0.0483 (10)
H19	0.0509	0.0704	0.3113	0.058*
O1	0.07883 (11)	0.09304 (18)	0.16115 (11)	0.0348 (6)
O2	0.02276 (13)	−0.6151 (2)	0.07916 (13)	0.0469 (7)
O3	0.07785 (13)	−0.6563 (2)	0.18890 (13)	0.0527 (7)
H3	0.0690	−0.7336	0.1777	0.079*
P1	0.13600 (5)	−0.00176 (8)	0.19091 (5)	0.0298 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0234 (17)	0.0297 (18)	0.0285 (19)	0.0009 (14)	−0.0005 (14)	0.0021 (15)
C2	0.040 (2)	0.0334 (19)	0.030 (2)	−0.0041 (17)	−0.0055 (16)	0.0100 (16)
C3	0.033 (2)	0.037 (2)	0.029 (2)	−0.0061 (17)	−0.0061 (15)	−0.0037 (16)
C4	0.0237 (18)	0.0276 (18)	0.033 (2)	−0.0006 (15)	−0.0004 (15)	0.0024 (15)
C5	0.041 (2)	0.0318 (19)	0.032 (2)	0.0044 (17)	−0.0061 (16)	0.0088 (16)
C6	0.036 (2)	0.034 (2)	0.028 (2)	0.0016 (17)	−0.0059 (15)	−0.0018 (16)
C7	0.029 (2)	0.038 (2)	0.035 (2)	−0.0020 (17)	0.0025 (16)	0.0019 (18)
C8	0.0320 (19)	0.0346 (19)	0.0243 (18)	−0.0038 (17)	−0.0057 (14)	−0.0023 (16)
C9	0.041 (2)	0.039 (2)	0.040 (2)	−0.0025 (18)	−0.0021 (18)	−0.0019 (17)
C10	0.037 (2)	0.059 (3)	0.044 (2)	0.001 (2)	0.0037 (18)	−0.005 (2)
C11	0.034 (2)	0.070 (3)	0.032 (2)	−0.008 (2)	0.0045 (16)	−0.003 (2)
C12	0.050 (2)	0.048 (2)	0.041 (2)	−0.014 (2)	0.0019 (19)	0.0049 (19)
C13	0.037 (2)	0.042 (2)	0.039 (2)	−0.0014 (18)	−0.0004 (17)	−0.0004 (18)
C14	0.0297 (19)	0.0278 (19)	0.034 (2)	−0.0020 (15)	−0.0006 (15)	−0.0029 (15)
C15	0.0323 (19)	0.048 (2)	0.035 (2)	−0.0013 (18)	0.0005 (15)	−0.0020 (19)
C16	0.041 (2)	0.060 (3)	0.041 (2)	−0.003 (2)	−0.0068 (18)	0.000 (2)
C17	0.062 (3)	0.065 (3)	0.028 (2)	−0.005 (2)	0.0014 (19)	−0.0037 (19)
C18	0.049 (3)	0.091 (3)	0.039 (2)	0.008 (2)	0.0107 (19)	−0.013 (2)
C19	0.035 (2)	0.068 (3)	0.042 (2)	0.006 (2)	−0.0018 (18)	−0.009 (2)
O1	0.0290 (12)	0.0307 (12)	0.0442 (15)	0.0002 (11)	−0.0080 (11)	0.0026 (11)
O2	0.0594 (17)	0.0369 (14)	0.0436 (16)	−0.0040 (12)	−0.0152 (13)	−0.0018 (12)
O3	0.0748 (18)	0.0269 (13)	0.0553 (18)	−0.0046 (13)	−0.0226 (14)	0.0037 (12)
P1	0.0285 (5)	0.0294 (5)	0.0314 (5)	−0.0020 (4)	−0.0029 (4)	−0.0002 (4)

Geometric parameters (Å, º) top

C1—C6	1.384 (4)	C10—H10	0.9300
C1—C2	1.391 (4)	C11—C12	1.375 (4)
C1—P1	1.802 (3)	C11—H11	0.9300
C2—C3	1.384 (4)	C12—C13	1.390 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.388 (4)	C13—H13	0.9300
C3—H3A	0.9300	C14—C15	1.382 (4)
C4—C5	1.381 (4)	C14—C19	1.385 (4)
C4—C7	1.499 (4)	C14—P1	1.793 (3)
C5—C6	1.384 (4)	C15—C16	1.379 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.380 (5)
C7—O2	1.199 (3)	C16—H16	0.9300
C7—O3	1.322 (3)	C17—C18	1.380 (4)
C8—C13	1.385 (4)	C17—H17	0.9300
C8—C9	1.389 (4)	C18—C19	1.374 (5)
C8—P1	1.793 (3)	C18—H18	0.9300
C9—C10	1.392 (4)	C19—H19	0.9300
C9—H9	0.9300	O1—P1	1.4952 (19)
C10—C11	1.371 (4)	O3—H3	0.8200

C6—C1—C2	118.8 (3)	C12—C11—H11	120.1
C6—C1—P1	122.5 (2)	C11—C12—C13	119.8 (3)
C2—C1—P1	118.7 (2)	C11—C12—H12	120.1
C3—C2—C1	121.0 (3)	C13—C12—H12	120.1
C3—C2—H2	119.5	C8—C13—C12	121.1 (3)
C1—C2—H2	119.5	C8—C13—H13	119.4
C2—C3—C4	119.6 (3)	C12—C13—H13	119.4
C2—C3—H3A	120.2	C15—C14—C19	118.8 (3)
C4—C3—H3A	120.2	C15—C14—P1	123.7 (3)
C5—C4—C3	119.6 (3)	C19—C14—P1	117.5 (2)
C5—C4—C7	121.6 (3)	C16—C15—C14	120.7 (3)
C3—C4—C7	118.8 (3)	C16—C15—H15	119.7
C4—C5—C6	120.5 (3)	C14—C15—H15	119.7
C4—C5—H5	119.7	C15—C16—C17	120.1 (3)
C6—C5—H5	119.7	C15—C16—H16	120.0
C5—C6—C1	120.4 (3)	C17—C16—H16	120.0
C5—C6—H6	119.8	C18—C17—C16	119.6 (3)
C1—C6—H6	119.8	C18—C17—H17	120.2
O2—C7—O3	124.3 (3)	C16—C17—H17	120.2
O2—C7—C4	124.0 (3)	C19—C18—C17	120.2 (4)
O3—C7—C4	111.7 (3)	C19—C18—H18	119.9
C13—C8—C9	118.4 (3)	C17—C18—H18	119.9
C13—C8—P1	118.5 (3)	C18—C19—C14	120.7 (3)
C9—C8—P1	123.1 (3)	C18—C19—H19	119.6
C8—C9—C10	120.2 (3)	C14—C19—H19	119.6
C8—C9—H9	119.9	C7—O3—H3	109.5
C10—C9—H9	119.9	O1—P1—C8	111.49 (14)
C11—C10—C9	120.6 (3)	O1—P1—C14	112.67 (13)
C11—C10—H10	119.7	C8—P1—C14	107.23 (14)
C9—C10—H10	119.7	O1—P1—C1	111.40 (12)
C10—C11—C12	119.8 (3)	C8—P1—C1	106.75 (14)
C10—C11—H11	120.1	C14—P1—C1	106.98 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.82	1.78	2.579 (3)	163

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅O₃P
M_r	322.28
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	18.018 (3), 10.0921 (18), 18.028 (4)
β (°)	91.467 (4)
V (Å³)	3277.1 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.24 × 0.21 × 0.17

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SAINT; Bruker, 1998)
T_min, T_max	0.956, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	8975, 3228, 1796
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.110, 0.91
No. of reflections	3228
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.25

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.82	1.78	2.579 (3)	162.6

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors thank Beihua University for supporting this work.

References

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Etter, M. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Fuquen, R. M. & Lechat, J. R. (1992). Acta Cryst. C48, 1690–1692. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
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