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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2074.
Published online 2008 October 4. doi:  10.1107/S1600536808031449
PMCID: PMC2959504

4-(Diphenyl­phosphino­yl)benzoic acid

Abstract

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 [triangle]). For related structures, see: Etter (1990 [triangle]); Fuquen & Lechat (1992 [triangle]).

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Object name is e-64-o2074-scheme1.jpg

Experimental

Crystal data

  • C19H15O3P
  • M r = 322.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2074-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.110
  • S = 0.91
  • 3228 reflections
  • 208 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

The authors thank Beihua University for supporting this work.

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

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.

Crystal data

C19H15O3PF(000) = 1344
Mr = 322.28Dx = 1.306 Mg m3
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 mm1
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

Bruker APEX CCD area-detector diffractometer3228 independent reflections
Radiation source: fine-focus sealed tube1796 reflections with I > 2σ(I)
graphiteRint = 0.079
[var phi] 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

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 = 0.91w = 1/[σ2(Fo2) + (0.0279P)2] where P = (Fo2 + 2Fc2)/3
3228 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.25 e Å3

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 (Å2)

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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.821.782.579 (3)163

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2800).

References

  • Al-Farhan, K. A. (1992). J. Chem. Crystallogr.22, 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. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography