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organic compounds
4-(Diphenylphosphanyl)benzoic acid
aResearch Center for Engineering Technology of Polymeric Composites of Shanxi Province, School of Materials Science and Engineering, North University of China, Taiyuan 030051, People's Republic of China
*Correspondence e-mail: zph2004@yahoo.com.cn
In the title compound, C19H15O2P, the dihedral angles between the benzoic acid ring and the phenyl rings are 75.64 (7) and 80.88 (7)°; the dihedral angle between the phenyl rings is 81.35 (7)°. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R22(8) loops between the head-to-head carboxylic acid groups.
Related literature
For background to phosphine ligands, see: Dydio et al. (2011). For water-soluble see: Katti et al. (1999
); Pinault & Bruce (2003
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; 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: SHELXL97.
Supporting information
10.1107/S1600536811034234/hb6381sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811034234/hb6381Isup4.hkl
Supporting information file. DOI: 10.1107/S1600536811034234/hb6381Isup3.cml
4-iodobenzoic acid (5.0 mmol) and Et3N (10 mmol) were dissolved in CH3CN (30 ml). After the addition of Pb(OAc)2 (0.005 mmol) and Ph2PH (5.0 mmol), the reaction mixture was refluxed for 12 h. All volatiles were removed in vacuo and the obtained residue was dissolved in H2O (15 ml). After addition of KOH (10.0 mmol), the solution was extracted with Et2O. The aqueous solution was acidified with 2 N HCl and again extracted with Et2O. The collected ethereal phases were washed with H2O, dried over MgSO4 and evaporated to get a white precipite. Colourless prisms of (I) were obtained by recrystallization from MeOH at room temperature.
All the H atoms were positioned geometrically (O—H = 0.84 Å, C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: SHELXL97 (Sheldrick, 2008).C19H15O2P | F(000) = 640 |
Mr = 306.28 | Dx = 1.286 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.885 (2) Å | Cell parameters from 5302 reflections |
b = 28.629 (8) Å | θ = 1.4–28.0° |
c = 7.066 (2) Å | µ = 0.18 mm−1 |
β = 97.338 (4)° | T = 113 K |
V = 1581.8 (8) Å3 | Prism, colorless |
Z = 4 | 0.24 × 0.20 × 0.20 mm |
Rigaku Saturn724 CCD diffractometer | 3714 independent reflections |
Radiation source: rotating anode | 3066 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.049 |
Detector resolution: 14.22 pixels mm-1 | θmax = 27.9°, θmin = 1.4° |
ω and ϕ scans | h = −10→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −37→36 |
Tmin = 0.959, Tmax = 0.965 | l = −9→8 |
15613 measured reflections |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.046P] where P = (Fo2 + 2Fc2)/3 |
3714 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C19H15O2P | V = 1581.8 (8) Å3 |
Mr = 306.28 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.885 (2) Å | µ = 0.18 mm−1 |
b = 28.629 (8) Å | T = 113 K |
c = 7.066 (2) Å | 0.24 × 0.20 × 0.20 mm |
β = 97.338 (4)° |
Rigaku Saturn724 CCD diffractometer | 3714 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 3066 reflections with I > 2σ(I) |
Tmin = 0.959, Tmax = 0.965 | Rint = 0.049 |
15613 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.25 e Å−3 |
3714 reflections | Δρmin = −0.30 e Å−3 |
200 parameters |
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 | Uiso*/Ueq | ||
P1 | 0.20334 (5) | 0.395759 (13) | 0.81304 (6) | 0.02428 (13) | |
O1 | −0.31468 (15) | 0.46619 (4) | 0.02047 (16) | 0.0387 (3) | |
H1 | −0.3963 | 0.4778 | −0.0527 | 0.058* | |
O2 | −0.45337 (13) | 0.49967 (3) | 0.24140 (15) | 0.0326 (3) | |
C1 | 0.04771 (17) | 0.41954 (5) | 0.6200 (2) | 0.0232 (3) | |
C2 | 0.04539 (18) | 0.40779 (5) | 0.4285 (2) | 0.0262 (3) | |
H2 | 0.1286 | 0.3867 | 0.3921 | 0.031* | |
C3 | −0.07624 (18) | 0.42632 (5) | 0.2905 (2) | 0.0259 (3) | |
H3 | −0.0758 | 0.4181 | 0.1603 | 0.031* | |
C4 | −0.19939 (17) | 0.45701 (5) | 0.3423 (2) | 0.0234 (3) | |
C5 | −0.19788 (18) | 0.46940 (5) | 0.5334 (2) | 0.0245 (3) | |
H5 | −0.2817 | 0.4903 | 0.5696 | 0.029* | |
C6 | −0.07421 (18) | 0.45129 (5) | 0.6702 (2) | 0.0248 (3) | |
H6 | −0.0719 | 0.4605 | 0.7997 | 0.030* | |
C7 | −0.33261 (18) | 0.47604 (5) | 0.1953 (2) | 0.0261 (3) | |
C8 | 0.07195 (17) | 0.35227 (5) | 0.9178 (2) | 0.0221 (3) | |
C9 | −0.09792 (18) | 0.34255 (5) | 0.8492 (2) | 0.0268 (3) | |
H9 | −0.1503 | 0.3581 | 0.7382 | 0.032* | |
C10 | −0.19171 (19) | 0.31060 (5) | 0.9399 (2) | 0.0302 (4) | |
H10 | −0.3080 | 0.3048 | 0.8920 | 0.036* | |
C11 | −0.1167 (2) | 0.28692 (5) | 1.1006 (2) | 0.0297 (3) | |
H11 | −0.1803 | 0.2646 | 1.1618 | 0.036* | |
C12 | 0.0520 (2) | 0.29624 (5) | 1.1706 (2) | 0.0295 (3) | |
H12 | 0.1042 | 0.2802 | 1.2806 | 0.035* | |
C13 | 0.14521 (18) | 0.32874 (5) | 1.0817 (2) | 0.0266 (3) | |
H13 | 0.2603 | 0.3351 | 1.1326 | 0.032* | |
C14 | 0.33456 (17) | 0.35885 (5) | 0.6768 (2) | 0.0233 (3) | |
C15 | 0.31532 (17) | 0.31046 (5) | 0.6575 (2) | 0.0250 (3) | |
H15 | 0.2309 | 0.2949 | 0.7187 | 0.030* | |
C16 | 0.41838 (19) | 0.28490 (5) | 0.5498 (2) | 0.0271 (3) | |
H16 | 0.4057 | 0.2520 | 0.5401 | 0.033* | |
C17 | 0.53902 (18) | 0.30724 (5) | 0.4571 (2) | 0.0281 (3) | |
H17 | 0.6082 | 0.2897 | 0.3822 | 0.034* | |
C18 | 0.55916 (18) | 0.35529 (5) | 0.4733 (2) | 0.0286 (3) | |
H18 | 0.6411 | 0.3708 | 0.4079 | 0.034* | |
C19 | 0.45977 (17) | 0.38077 (5) | 0.5848 (2) | 0.0264 (3) | |
H19 | 0.4770 | 0.4135 | 0.5989 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0209 (2) | 0.0242 (2) | 0.0281 (2) | −0.00146 (13) | 0.00446 (15) | −0.00451 (15) |
O1 | 0.0387 (7) | 0.0520 (7) | 0.0271 (6) | 0.0213 (5) | 0.0104 (5) | 0.0035 (5) |
O2 | 0.0329 (6) | 0.0343 (6) | 0.0329 (6) | 0.0142 (4) | 0.0136 (5) | 0.0035 (5) |
C1 | 0.0228 (7) | 0.0185 (6) | 0.0295 (8) | −0.0019 (5) | 0.0077 (6) | −0.0022 (6) |
C2 | 0.0253 (7) | 0.0236 (7) | 0.0308 (8) | 0.0051 (5) | 0.0071 (6) | −0.0041 (6) |
C3 | 0.0282 (7) | 0.0253 (7) | 0.0261 (8) | 0.0035 (6) | 0.0105 (6) | −0.0032 (6) |
C4 | 0.0234 (7) | 0.0201 (6) | 0.0285 (8) | 0.0018 (5) | 0.0106 (6) | 0.0026 (6) |
C5 | 0.0249 (7) | 0.0190 (6) | 0.0323 (9) | 0.0022 (5) | 0.0143 (6) | 0.0002 (6) |
C6 | 0.0281 (7) | 0.0224 (7) | 0.0261 (8) | −0.0005 (5) | 0.0119 (6) | −0.0023 (6) |
C7 | 0.0275 (7) | 0.0227 (7) | 0.0305 (9) | 0.0042 (5) | 0.0126 (6) | 0.0028 (6) |
C8 | 0.0217 (7) | 0.0232 (7) | 0.0217 (8) | 0.0015 (5) | 0.0038 (5) | −0.0049 (6) |
C9 | 0.0243 (7) | 0.0301 (7) | 0.0255 (8) | −0.0008 (6) | 0.0008 (6) | 0.0034 (6) |
C10 | 0.0260 (8) | 0.0323 (8) | 0.0323 (9) | −0.0033 (6) | 0.0037 (6) | 0.0014 (7) |
C11 | 0.0371 (9) | 0.0264 (7) | 0.0276 (9) | 0.0009 (6) | 0.0121 (7) | 0.0003 (6) |
C12 | 0.0381 (9) | 0.0291 (8) | 0.0214 (8) | 0.0092 (6) | 0.0042 (6) | 0.0000 (6) |
C13 | 0.0241 (7) | 0.0302 (8) | 0.0249 (8) | 0.0061 (6) | 0.0004 (6) | −0.0065 (6) |
C14 | 0.0177 (6) | 0.0264 (7) | 0.0254 (8) | 0.0013 (5) | 0.0012 (5) | −0.0015 (6) |
C15 | 0.0216 (7) | 0.0257 (7) | 0.0279 (8) | −0.0022 (5) | 0.0039 (6) | 0.0002 (6) |
C16 | 0.0268 (7) | 0.0248 (7) | 0.0297 (9) | 0.0028 (5) | 0.0035 (6) | −0.0016 (6) |
C17 | 0.0224 (7) | 0.0345 (8) | 0.0274 (8) | 0.0064 (6) | 0.0031 (6) | −0.0021 (6) |
C18 | 0.0195 (7) | 0.0338 (8) | 0.0330 (9) | −0.0004 (5) | 0.0060 (6) | 0.0047 (7) |
C19 | 0.0205 (7) | 0.0261 (7) | 0.0328 (9) | −0.0023 (5) | 0.0037 (6) | 0.0013 (6) |
P1—C8 | 1.8348 (15) | C9—H9 | 0.9500 |
P1—C14 | 1.8351 (15) | C10—C11 | 1.388 (2) |
P1—C1 | 1.8443 (15) | C10—H10 | 0.9500 |
O1—C7 | 1.2920 (19) | C11—C12 | 1.384 (2) |
O1—H1 | 0.8400 | C11—H11 | 0.9500 |
O2—C7 | 1.2449 (17) | C12—C13 | 1.385 (2) |
C1—C2 | 1.392 (2) | C12—H12 | 0.9500 |
C1—C6 | 1.4012 (19) | C13—H13 | 0.9500 |
C2—C3 | 1.383 (2) | C14—C19 | 1.3980 (19) |
C2—H2 | 0.9500 | C14—C15 | 1.398 (2) |
C3—C4 | 1.3927 (19) | C15—C16 | 1.390 (2) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C4—C5 | 1.395 (2) | C16—C17 | 1.379 (2) |
C4—C7 | 1.484 (2) | C16—H16 | 0.9500 |
C5—C6 | 1.383 (2) | C17—C18 | 1.388 (2) |
C5—H5 | 0.9500 | C17—H17 | 0.9500 |
C6—H6 | 0.9500 | C18—C19 | 1.388 (2) |
C8—C9 | 1.3930 (19) | C18—H18 | 0.9500 |
C8—C13 | 1.399 (2) | C19—H19 | 0.9500 |
C9—C10 | 1.384 (2) | ||
C8—P1—C14 | 101.89 (7) | C9—C10—C11 | 120.28 (14) |
C8—P1—C1 | 101.07 (6) | C9—C10—H10 | 119.9 |
C14—P1—C1 | 101.02 (7) | C11—C10—H10 | 119.9 |
C7—O1—H1 | 109.5 | C12—C11—C10 | 119.20 (14) |
C2—C1—C6 | 118.58 (13) | C12—C11—H11 | 120.4 |
C2—C1—P1 | 123.67 (11) | C10—C11—H11 | 120.4 |
C6—C1—P1 | 117.75 (11) | C11—C12—C13 | 120.57 (14) |
C3—C2—C1 | 120.97 (13) | C11—C12—H12 | 119.7 |
C3—C2—H2 | 119.5 | C13—C12—H12 | 119.7 |
C1—C2—H2 | 119.5 | C12—C13—C8 | 120.79 (13) |
C2—C3—C4 | 120.02 (14) | C12—C13—H13 | 119.6 |
C2—C3—H3 | 120.0 | C8—C13—H13 | 119.6 |
C4—C3—H3 | 120.0 | C19—C14—C15 | 118.26 (13) |
C3—C4—C5 | 119.67 (13) | C19—C14—P1 | 117.67 (11) |
C3—C4—C7 | 120.17 (13) | C15—C14—P1 | 124.07 (11) |
C5—C4—C7 | 120.15 (13) | C16—C15—C14 | 120.74 (14) |
C6—C5—C4 | 119.94 (13) | C16—C15—H15 | 119.6 |
C6—C5—H5 | 120.0 | C14—C15—H15 | 119.6 |
C4—C5—H5 | 120.0 | C17—C16—C15 | 120.19 (14) |
C5—C6—C1 | 120.78 (14) | C17—C16—H16 | 119.9 |
C5—C6—H6 | 119.6 | C15—C16—H16 | 119.9 |
C1—C6—H6 | 119.6 | C16—C17—C18 | 119.93 (14) |
O2—C7—O1 | 123.34 (14) | C16—C17—H17 | 120.0 |
O2—C7—C4 | 120.86 (14) | C18—C17—H17 | 120.0 |
O1—C7—C4 | 115.80 (13) | C19—C18—C17 | 120.06 (14) |
C9—C8—C13 | 117.94 (13) | C19—C18—H18 | 120.0 |
C9—C8—P1 | 124.24 (11) | C17—C18—H18 | 120.0 |
C13—C8—P1 | 117.76 (10) | C18—C19—C14 | 120.79 (14) |
C10—C9—C8 | 121.20 (13) | C18—C19—H19 | 119.6 |
C10—C9—H9 | 119.4 | C14—C19—H19 | 119.6 |
C8—C9—H9 | 119.4 | ||
C8—P1—C1—C2 | −102.98 (13) | C1—P1—C8—C13 | −175.39 (11) |
C14—P1—C1—C2 | 1.61 (13) | C13—C8—C9—C10 | −0.1 (2) |
C8—P1—C1—C6 | 77.23 (12) | P1—C8—C9—C10 | −177.35 (11) |
C14—P1—C1—C6 | −178.18 (11) | C8—C9—C10—C11 | −1.0 (2) |
C6—C1—C2—C3 | −1.1 (2) | C9—C10—C11—C12 | 1.1 (2) |
P1—C1—C2—C3 | 179.08 (11) | C10—C11—C12—C13 | −0.1 (2) |
C1—C2—C3—C4 | −0.4 (2) | C11—C12—C13—C8 | −1.0 (2) |
C2—C3—C4—C5 | 0.9 (2) | C9—C8—C13—C12 | 1.1 (2) |
C2—C3—C4—C7 | −178.49 (13) | P1—C8—C13—C12 | 178.52 (11) |
C3—C4—C5—C6 | 0.1 (2) | C8—P1—C14—C19 | −176.36 (10) |
C7—C4—C5—C6 | 179.51 (12) | C1—P1—C14—C19 | 79.70 (11) |
C4—C5—C6—C1 | −1.7 (2) | C8—P1—C14—C15 | 4.54 (13) |
C2—C1—C6—C5 | 2.2 (2) | C1—P1—C14—C15 | −99.40 (12) |
P1—C1—C6—C5 | −178.05 (10) | C19—C14—C15—C16 | 0.10 (19) |
C3—C4—C7—O2 | 172.69 (14) | P1—C14—C15—C16 | 179.19 (10) |
C5—C4—C7—O2 | −6.7 (2) | C14—C15—C16—C17 | −1.4 (2) |
C3—C4—C7—O1 | −6.9 (2) | C15—C16—C17—C18 | 0.8 (2) |
C5—C4—C7—O1 | 173.76 (13) | C16—C17—C18—C19 | 0.9 (2) |
C14—P1—C8—C9 | −102.00 (13) | C17—C18—C19—C14 | −2.2 (2) |
C1—P1—C8—C9 | 1.90 (14) | C15—C14—C19—C18 | 1.7 (2) |
C14—P1—C8—C13 | 80.71 (12) | P1—C14—C19—C18 | −177.48 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.79 | 2.6190 (16) | 170 |
Symmetry code: (i) −x−1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C19H15O2P |
Mr | 306.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 7.885 (2), 28.629 (8), 7.066 (2) |
β (°) | 97.338 (4) |
V (Å3) | 1581.8 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.24 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Rigaku Saturn724 CCD diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.959, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15613, 3714, 3066 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.109, 1.03 |
No. of reflections | 3714 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.30 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.79 | 2.6190 (16) | 170 |
Symmetry code: (i) −x−1, −y+1, −z. |
Acknowledgements
This work was supported financially by the start-up foundation of North University of China.
References
Dydio, P., Dzik, W. I., Lutz, M., De Bruin, B. & Peek, J. N. H. (2011). Angew. Chem. Int. Ed. 50, 396–400. CrossRef CAS Google Scholar
Katti, K. V., Gall, H., Smith, C. J. & Berning, D. E. (1999). Acc. Chem. Res. 32, 9–17. CrossRef CAS Google Scholar
Pinault, N. & Bruce, D. W. (2003). Coord. Chem. Rev. 241, 1–25. CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Phosphine ligands are important intermediates in organic chemistry e.g. (Dydio et al., 2011), Water-soluble phosphines with the hydrophobic group are the most common phosphine lingands used in catalytic and biomedical aspects (Katti et al., 1999; Pinault & Bruce, 2003). The title compound, (I), belongs to the fuctionalized water-soluble phosphines.
The O—H···O hydrogen bonds between the O atom of the carbonyl group and the H atom of the carboxyl group link the molecules into inversion dimers (Table 1).