4-(Diphenyl-phosphan-yl)benzoic acid.

In the title compound, C(19)H(15)O(2)P, 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 R(2) (2)(8) loops between the head-to-head carb-oxy-lic acid groups.

Related literature

For background to phosphine ligands, see: Dydio et al. (2011 ▶). For water-soluble phosphines, see: Katti et al. (1999 ▶); Pinault & Bruce (2003 ▶).

Experimental

Crystal data

C19H15O2P

M = 306.28

Monoclinic,

a = 7.885 (2) Å

b = 28.629 (8) Å

c = 7.066 (2) Å

β = 97.338 (4)°

V = 1581.8 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 113 K

0.24 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.959, T max = 0.965

15613 measured reflections

3714 independent reflections

3066 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.03

3714 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034234/hb6381sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034234/hb6381Isup4.hkl

Supplementary material file. DOI: 10.1107/S1600536811034234/hb6381Isup3.cml

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

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	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

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

Table 1

Hydrogen-bond geometry (Å, °)

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) .