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Acta Cryst. (2008). E64, o2074    [ doi:10.1107/S1600536808031449 ]

4-(Diphenylphosphinoyl)benzoic acid

Y.-J. Li and R.-C. Zhang

Abstract top

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.

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.

Refinement top

All H atoms were positioned geometrically (O—H = 0.82 Å, C—H = 0.93 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C,O).

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
[Figure 1] Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] 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
C19H15O3PF(000) = 1344
Mr = 322.28Dx = 1.306 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3228 reflections
a = 18.018 (3) Åθ = 1.1–26.0°
b = 10.0921 (18) ŵ = 0.18 mm−1
c = 18.028 (4) ÅT = 293 K
β = 91.467 (4)°Block, white
V = 3277.1 (11) Å30.24 × 0.21 × 0.17 mm
Z = 8
Data collection top
Bruker APEX CCD area-detector
diffractometer		3228 independent reflections
Radiation source: fine-focus sealed tube1796 reflections with I > 2σ(I)
graphiteRint = 0.079
φ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SAINT; Bruker, 1998)		h = −22→16
Tmin = 0.956, Tmax = 0.971k = −11→12
8975 measured reflectionsl = −21→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 0.91 w = 1/[σ2(Fo2) + (0.0279P)2]
where P = (Fo2 + 2Fc2)/3
3228 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C19H15O3PV = 3277.1 (11) Å3
Mr = 322.28Z = 8
Monoclinic, C2/cMo Kα radiation
a = 18.018 (3) ŵ = 0.18 mm−1
b = 10.0921 (18) ÅT = 293 K
c = 18.028 (4) Å0.24 × 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)
Tmin = 0.956, Tmax = 0.971Rint = 0.079
8975 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.110Δρmax = 0.38 e Å−3
S = 0.91Δρmin = −0.25 e Å−3
3228 reflectionsAbsolute structure: ?
208 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
C10.10622 (15)−0.1711 (3)0.17928 (17)0.0272 (7)
C20.07579 (16)−0.2100 (3)0.11102 (17)0.0346 (8)
H20.0682−0.14710.07380.041*
C30.05660 (16)−0.3408 (3)0.09760 (17)0.0332 (8)
H3A0.0367−0.36580.05160.040*
C40.06720 (16)−0.4344 (3)0.15324 (17)0.0283 (8)
C50.09413 (17)−0.3952 (3)0.22220 (17)0.0353 (9)
H50.0994−0.45720.26010.042*
C60.11340 (16)−0.2644 (3)0.23532 (17)0.0330 (8)
H60.1313−0.23900.28200.040*
C70.05236 (17)−0.5773 (3)0.13561 (19)0.0342 (8)
C80.22186 (16)0.0143 (3)0.14358 (16)0.0304 (8)
C90.27202 (18)−0.0893 (3)0.13654 (18)0.0401 (9)
H90.2615−0.17180.15660.048*
C100.33799 (19)−0.0698 (4)0.0995 (2)0.0466 (10)
H100.3713−0.13960.09510.056*
C110.35436 (19)0.0512 (4)0.06954 (18)0.0453 (10)
H110.39860.06330.04490.054*
C120.30524 (19)0.1546 (4)0.07603 (19)0.0463 (10)
H120.31610.23690.05580.056*
C130.23927 (18)0.1359 (3)0.11296 (18)0.0395 (9)
H130.20630.20620.11720.047*
C140.15618 (17)0.0219 (3)0.28792 (17)0.0307 (8)
C150.22564 (17)0.0031 (3)0.32047 (18)0.0384 (8)
H150.2650−0.02250.29140.046*
C160.2371 (2)0.0220 (3)0.3956 (2)0.0473 (10)
H160.28430.01060.41680.057*
C170.1788 (2)0.0578 (3)0.4395 (2)0.0516 (10)
H170.18640.07060.49020.062*
C180.1090 (2)0.0743 (4)0.4076 (2)0.0597 (11)
H180.06920.09690.43700.072*
C190.09794 (19)0.0576 (3)0.3324 (2)0.0483 (10)
H190.05090.07040.31130.058*
O10.07883 (11)0.09304 (18)0.16115 (11)0.0348 (6)
O20.02276 (13)−0.6151 (2)0.07916 (13)0.0469 (7)
O30.07785 (13)−0.6563 (2)0.18890 (13)0.0527 (7)
H30.0690−0.73360.17770.079*
P10.13600 (5)−0.00176 (8)0.19091 (5)0.0298 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0234 (17)0.0297 (18)0.0285 (19)0.0009 (14)−0.0005 (14)0.0021 (15)
C20.040 (2)0.0334 (19)0.030 (2)−0.0041 (17)−0.0055 (16)0.0100 (16)
C30.033 (2)0.037 (2)0.029 (2)−0.0061 (17)−0.0061 (15)−0.0037 (16)
C40.0237 (18)0.0276 (18)0.033 (2)−0.0006 (15)−0.0004 (15)0.0024 (15)
C50.041 (2)0.0318 (19)0.032 (2)0.0044 (17)−0.0061 (16)0.0088 (16)
C60.036 (2)0.034 (2)0.028 (2)0.0016 (17)−0.0059 (15)−0.0018 (16)
C70.029 (2)0.038 (2)0.035 (2)−0.0020 (17)0.0025 (16)0.0019 (18)
C80.0320 (19)0.0346 (19)0.0243 (18)−0.0038 (17)−0.0057 (14)−0.0023 (16)
C90.041 (2)0.039 (2)0.040 (2)−0.0025 (18)−0.0021 (18)−0.0019 (17)
C100.037 (2)0.059 (3)0.044 (2)0.001 (2)0.0037 (18)−0.005 (2)
C110.034 (2)0.070 (3)0.032 (2)−0.008 (2)0.0045 (16)−0.003 (2)
C120.050 (2)0.048 (2)0.041 (2)−0.014 (2)0.0019 (19)0.0049 (19)
C130.037 (2)0.042 (2)0.039 (2)−0.0014 (18)−0.0004 (17)−0.0004 (18)
C140.0297 (19)0.0278 (19)0.034 (2)−0.0020 (15)−0.0006 (15)−0.0029 (15)
C150.0323 (19)0.048 (2)0.035 (2)−0.0013 (18)0.0005 (15)−0.0020 (19)
C160.041 (2)0.060 (3)0.041 (2)−0.003 (2)−0.0068 (18)0.000 (2)
C170.062 (3)0.065 (3)0.028 (2)−0.005 (2)0.0014 (19)−0.0037 (19)
C180.049 (3)0.091 (3)0.039 (2)0.008 (2)0.0107 (19)−0.013 (2)
C190.035 (2)0.068 (3)0.042 (2)0.006 (2)−0.0018 (18)−0.009 (2)
O10.0290 (12)0.0307 (12)0.0442 (15)0.0002 (11)−0.0080 (11)0.0026 (11)
O20.0594 (17)0.0369 (14)0.0436 (16)−0.0040 (12)−0.0152 (13)−0.0018 (12)
O30.0748 (18)0.0269 (13)0.0553 (18)−0.0046 (13)−0.0226 (14)0.0037 (12)
P10.0285 (5)0.0294 (5)0.0314 (5)−0.0020 (4)−0.0029 (4)−0.0002 (4)
Geometric parameters (Å, °) top
C1—C61.384 (4)C10—H100.9300
C1—C21.391 (4)C11—C121.375 (4)
C1—P11.802 (3)C11—H110.9300
C2—C31.384 (4)C12—C131.390 (4)
C2—H20.9300C12—H120.9300
C3—C41.388 (4)C13—H130.9300
C3—H3A0.9300C14—C151.382 (4)
C4—C51.381 (4)C14—C191.385 (4)
C4—C71.499 (4)C14—P11.793 (3)
C5—C61.384 (4)C15—C161.379 (4)
C5—H50.9300C15—H150.9300
C6—H60.9300C16—C171.380 (5)
C7—O21.199 (3)C16—H160.9300
C7—O31.322 (3)C17—C181.380 (4)
C8—C131.385 (4)C17—H170.9300
C8—C91.389 (4)C18—C191.374 (5)
C8—P11.793 (3)C18—H180.9300
C9—C101.392 (4)C19—H190.9300
C9—H90.9300O1—P11.4952 (19)
C10—C111.371 (4)O3—H30.8200
C6—C1—C2118.8 (3)C12—C11—H11120.1
C6—C1—P1122.5 (2)C11—C12—C13119.8 (3)
C2—C1—P1118.7 (2)C11—C12—H12120.1
C3—C2—C1121.0 (3)C13—C12—H12120.1
C3—C2—H2119.5C8—C13—C12121.1 (3)
C1—C2—H2119.5C8—C13—H13119.4
C2—C3—C4119.6 (3)C12—C13—H13119.4
C2—C3—H3A120.2C15—C14—C19118.8 (3)
C4—C3—H3A120.2C15—C14—P1123.7 (3)
C5—C4—C3119.6 (3)C19—C14—P1117.5 (2)
C5—C4—C7121.6 (3)C16—C15—C14120.7 (3)
C3—C4—C7118.8 (3)C16—C15—H15119.7
C4—C5—C6120.5 (3)C14—C15—H15119.7
C4—C5—H5119.7C15—C16—C17120.1 (3)
C6—C5—H5119.7C15—C16—H16120.0
C5—C6—C1120.4 (3)C17—C16—H16120.0
C5—C6—H6119.8C18—C17—C16119.6 (3)
C1—C6—H6119.8C18—C17—H17120.2
O2—C7—O3124.3 (3)C16—C17—H17120.2
O2—C7—C4124.0 (3)C19—C18—C17120.2 (4)
O3—C7—C4111.7 (3)C19—C18—H18119.9
C13—C8—C9118.4 (3)C17—C18—H18119.9
C13—C8—P1118.5 (3)C18—C19—C14120.7 (3)
C9—C8—P1123.1 (3)C18—C19—H19119.6
C8—C9—C10120.2 (3)C14—C19—H19119.6
C8—C9—H9119.9C7—O3—H3109.5
C10—C9—H9119.9O1—P1—C8111.49 (14)
C11—C10—C9120.6 (3)O1—P1—C14112.67 (13)
C11—C10—H10119.7C8—P1—C14107.23 (14)
C9—C10—H10119.7O1—P1—C1111.40 (12)
C10—C11—C12119.8 (3)C8—P1—C1106.75 (14)
C10—C11—H11120.1C14—P1—C1106.98 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.821.782.579 (3)163
Symmetry codes: (i) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.821.782.579 (3)163
Symmetry codes: (i) x, y−1, z.
Acknowledgements top

The authors thank Beihua University for supporting this work.

references
References top

Al-Farhan, K. A. (1992). J. Chem. Crystallogr. 22, 6, 687–692.

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Etter, M. (1990). Acc. Chem. Res. 23, 120–126.

Fuquen, R. M. & Lechat, J. R. (1992). Acta Cryst. C48, 1690–1692.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.