2-(Di­phenyl­phosphinoyl)­benzoic acid chloro­form solvate

Burger, S.; Therrien, B.; Süss-Fink, G.

doi:10.1107/S1600536803018245

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2-(Diphenylphosphinoyl)benzoic acid chloroform solvate

S. Burger, B. Therrien and G. Süss-Fink

In the solid state, 2-(diphenylphosphinoyl)benzoic acid, (C₆H₄CO₂H)P(O)PPh₂, forms a hydrogen-bonded dimer between the phosphoryl O atom and the O-H group of the benzoic acid moiety, while the O atom of the carbonyl group is involved in an intramolecular contact with the P atom. The molecule exists as the chloroform solvate, C₁₉H₁₅O₃P·CHCl₃.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018245/om6164sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018245/om6164Isup2.hkl Contains datablock I

CCDC reference: 222886

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.006 Å
R factor = 0.051
wR factor = 0.126
Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               7227
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         7791
           Completeness (_total/calc)             92.76%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        C40
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O3     -   H3A      =       1.03 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O5     -   H5A      =       1.06 Ang.

   3 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Commercially available 2-(diphenylphosphino)benzoic acid has been recently used as a building block for the synthesis of more complex ligands (Wrobleski et al., 1984; Correia et al., 2001; Trost et al., 2002; Burger et al., 2003). The phosphine oxide derivative, (C₆H₄CO₂H)P(O)PPh₂, (I), was obtained in moderate yield by addition of hydrogen peroxide to a methanol solution containing 2-(diphenylphosphino)benzoic acid (Chandrasekaran et al., 2001). Unlike Chandrasekaran et al., who obtained crystals of (I) by slow evaporation of a CH₂Cl₂/heptane solution, we obtained crystals suitable for X-ray analysis by slow evaporation of a chloroform solution. The presence of chloroform molecules in the crystal generates a completely different mode of packing.

Compound (I) crystallizes with two independent molecules of (I) per asymmetric unit. Fig. 1 shows only one independent molecule of (I), and significant bond lengths and angles are given in Table 1. The P atom is in a pseudo-trigonal bipyramid geometry, the phosphoryl O atom being involved in an intramolecular contact with the O atom of the carbonyl group of the acid function, P1—O4 = 2.973 (3) Å and P2—O6 = 2.966 (3) Å. A similar axial coordination has been observed for (C₆H₄CO₂H)P(O)PPh₂ (Chandrasekaran et al., 2001) and the related compounds [Et₂NH₂][(C₆H₄CO₂)P(O)PPh₂] (Chandrasekaran et al., 2002) and [HN(CH₂C₆H₂Me₂OH)₃][(C₆H₄CO₂)P(O)PPh₂] (Chandrasekaran et al., 2003). In the solid state, compound (I) exists as dimers due to the presence of hydrogen bonds between the phosphoryl O atom and the O—H group of the benzoic acid moiety (Fig. 2). The O···O distances are 2.578 (3) and 2.566 (4) Å, with O—H···O angles of 166.1 and 166.4°, respectively. The distances observed between the two P atoms of the dimers are 6.904 (2) and 6.995 (2) Å, respectively. The chloroform molecules participate to the hydrogen-bonding network. The C—H group of the chloroform molecule interacts with the O atom of a carbonyl group, the C—O distances being 3.255 (5) and 3.355 (5) Å, with C—H···O angles of 170.0 and 139.0°, respectively.

Experimental top

Compound (I) was prepared according to the literature method of Chandrasekaran et al. (2001). Crystals suitable for X-ray analysis were obtained by slow evaporation of a chloroform solution.

Computing details top

Data collection: EXPOSE in IPDS Software (Stoe & Cie, 2000); cell refinement: CELL in IPDS Software; data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The molecular structure of one molecule of 2-(diphenylphosphinoyl)benzoic acid (Farrugia, 1997). H atoms and chloroform molecules have been omitted for clarity. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Dimeric structure of (I), showing the intermolecular hydrogen bonds. (Anger et al., 1991)

2-(Diphenylphosphinoyl)benzoic acid chloroform solvate top

Crystal data top

C₁₉H₁₅O₃P·CHCl₃	Z = 4
M_r = 441.65	F(000) = 904
Triclinic, P1	D_x = 1.477 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6828 (9) Å	Cell parameters from 8000 reflections
b = 13.3850 (14) Å	θ = 2.0–25.9°
c = 17.8678 (18) Å	µ = 0.56 mm⁻¹
α = 91.572 (12)°	T = 153 K
β = 98.950 (12)°	Plate, colourless
γ = 104.045 (12)°	0.53 × 0.30 × 0.12 mm
V = 1985.4 (4) Å³

Data collection top

Stoe IPDS diffractometer	7227 independent reflections
Radiation source: fine-focus sealed tube	4039 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
Detector resolution: 0.81Å pixels mm^-1	θ_max = 26.0°, θ_min = 2.3°
ϕ oscillation scans	h = −10→10
Absorption correction: multi-scan (Blessing, 1995)	k = −16→16
T_min = 0.884, T_max = 0.935	l = −21→21
15762 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0524P)²] where P = (F_o² + 2F_c²)/3
7227 reflections	(Δ/σ)_max = 0.001
487 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₉H₁₅O₃P·CHCl₃	γ = 104.045 (12)°
M_r = 441.65	V = 1985.4 (4) Å³
Triclinic, P1	Z = 4
a = 8.6828 (9) Å	Mo Kα radiation
b = 13.3850 (14) Å	µ = 0.56 mm⁻¹
c = 17.8678 (18) Å	T = 153 K
α = 91.572 (12)°	0.53 × 0.30 × 0.12 mm
β = 98.950 (12)°

Data collection top

Stoe IPDS diffractometer	7227 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	4039 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.935	R_int = 0.070
15762 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 0.97	Δρ_max = 0.38 e Å⁻³
7227 reflections	Δρ_min = −0.40 e Å⁻³
487 parameters

Special details top

Experimental. A crystal was mounted at 153 K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using Mo Kα graphite monochromated radiation. Image plate distance 70 mm, ϕ oscillation scans 0 − 200°, step Δϕ = 1.3°, 3 minutes per frame.

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	0.6919 (4)	0.2834 (3)	0.0448 (2)	0.0230 (8)
C2	0.7266 (5)	0.3896 (3)	0.0616 (2)	0.0281 (9)
H2	0.7843	0.4180	0.1088	0.034*
C3	0.6754 (5)	0.4535 (3)	0.0080 (2)	0.0338 (10)
H3	0.7032	0.5246	0.0190	0.041*
C4	0.5847 (5)	0.4130 (3)	−0.0605 (2)	0.0324 (10)
H4	0.5500	0.4562	−0.0957	0.039*
C5	0.5451 (5)	0.3075 (3)	−0.0771 (2)	0.0284 (9)
H5	0.4806	0.2798	−0.1231	0.034*
C6	0.5997 (4)	0.2424 (3)	−0.0264 (2)	0.0232 (8)
C7	0.5694 (4)	0.1301 (3)	−0.0504 (2)	0.0238 (8)
C8	0.9461 (4)	0.1801 (3)	0.0921 (2)	0.0213 (8)
C9	0.9749 (5)	0.0832 (3)	0.0999 (2)	0.0264 (9)
H9	0.8980	0.0303	0.1156	0.032*
C10	1.1160 (5)	0.0644 (3)	0.0847 (2)	0.0302 (9)
H10	1.1333	−0.0012	0.0897	0.036*
C11	1.2315 (5)	0.1416 (3)	0.0620 (2)	0.0340 (10)
H11	1.3275	0.1286	0.0526	0.041*
C12	1.2048 (5)	0.2388 (3)	0.0532 (3)	0.0369 (11)
H12	1.2829	0.2912	0.0378	0.044*
C13	1.0620 (5)	0.2581 (3)	0.0673 (2)	0.0323 (10)
H13	1.0431	0.3230	0.0602	0.039*
C14	0.8141 (4)	0.2754 (3)	0.2055 (2)	0.0221 (8)
C15	0.7058 (5)	0.2511 (3)	0.2557 (2)	0.0318 (10)
H15	0.6080	0.2029	0.2402	0.038*
C16	0.7418 (5)	0.2978 (3)	0.3292 (3)	0.0386 (11)
H16	0.6686	0.2812	0.3626	0.046*
C17	0.8863 (5)	0.3684 (3)	0.3516 (2)	0.0346 (10)
H17	0.9117	0.3990	0.4008	0.041*
C18	0.9942 (5)	0.3947 (3)	0.3027 (2)	0.0338 (10)
H18	1.0911	0.4436	0.3186	0.041*
C19	0.9597 (5)	0.3487 (3)	0.2297 (2)	0.0298 (9)
H19	1.0335	0.3666	0.1968	0.036*
C21	0.3793 (4)	0.7416 (3)	0.4457 (2)	0.0223 (8)
C22	0.3155 (5)	0.8190 (3)	0.4127 (2)	0.0280 (9)
H22	0.3849	0.8797	0.4022	0.034*
C23	0.1492 (5)	0.8072 (3)	0.3949 (2)	0.0305 (9)
H23	0.1089	0.8607	0.3743	0.037*
C24	0.0453 (4)	0.7164 (3)	0.4078 (2)	0.0301 (9)
H24	−0.0654	0.7081	0.3955	0.036*
C25	0.1060 (4)	0.6376 (3)	0.4391 (2)	0.0276 (9)
H25	0.0353	0.5758	0.4466	0.033*
C26	0.2711 (4)	0.6493 (3)	0.4597 (2)	0.0218 (8)
C27	0.3303 (4)	0.5666 (3)	0.5014 (2)	0.0215 (8)
C28	0.6474 (4)	0.8142 (3)	0.5672 (2)	0.0252 (9)
C29	0.7635 (5)	0.7838 (3)	0.6174 (3)	0.0341 (10)
H29	0.8151	0.7358	0.6014	0.041*
C30	0.8018 (6)	0.8257 (4)	0.6917 (3)	0.0455 (12)
H30	0.8795	0.8055	0.7255	0.055*
C31	0.7262 (6)	0.8970 (3)	0.7163 (3)	0.0418 (11)
H31	0.7534	0.9251	0.7662	0.050*
C32	0.6101 (5)	0.9262 (3)	0.6663 (3)	0.0368 (10)
H32	0.5586	0.9740	0.6827	0.044*
C33	0.5698 (5)	0.8855 (3)	0.5925 (2)	0.0301 (9)
H33	0.4907	0.9055	0.5593	0.036*
C34	0.6784 (4)	0.8679 (3)	0.4137 (2)	0.0262 (9)
C35	0.7691 (5)	0.9641 (3)	0.4458 (3)	0.0355 (10)
H35	0.7866	0.9781	0.4981	0.043*
C36	0.8334 (6)	1.0391 (4)	0.3996 (3)	0.0480 (13)
H36	0.8953	1.1030	0.4213	0.058*
C37	0.8069 (6)	1.0202 (4)	0.3221 (3)	0.0458 (13)
H37	0.8494	1.0713	0.2915	0.055*
C38	0.7173 (5)	0.9254 (4)	0.2902 (3)	0.0413 (11)
H38	0.6982	0.9128	0.2378	0.050*
C39	0.6553 (5)	0.8488 (3)	0.3353 (2)	0.0347 (10)
H39	0.5978	0.7841	0.3132	0.042*
C40	0.0783 (5)	0.7681 (3)	0.1381 (3)	0.0417 (11)
H40	0.0998	0.7954	0.0894	0.050*
C41	0.5031 (5)	0.5034 (4)	0.2808 (3)	0.0421 (11)
H41	0.5223	0.4850	0.3335	0.051*
O1	0.6369 (3)	0.10507 (19)	0.12224 (15)	0.0271 (6)
O2	0.6609 (3)	0.67295 (19)	0.45209 (16)	0.0284 (6)
O3	0.4246 (3)	0.08972 (19)	−0.08849 (15)	0.0280 (6)
H3A	0.4165	0.0139	−0.1037	0.050*
O4	0.6742 (3)	0.0840 (2)	−0.03550 (16)	0.0316 (7)
O5	0.2415 (3)	0.47293 (19)	0.47931 (16)	0.0313 (7)
H5A	0.2770	0.4175	0.5145	0.050*
O6	0.4448 (3)	0.58675 (19)	0.55234 (15)	0.0263 (6)
P1	0.76105 (11)	0.20146 (7)	0.11505 (6)	0.0214 (2)
P2	0.59709 (11)	0.76333 (7)	0.46966 (6)	0.0232 (2)
Cl1	0.25058 (16)	0.81741 (10)	0.20622 (7)	0.0528 (3)
Cl2	−0.08721 (18)	0.80776 (12)	0.16134 (12)	0.0862 (6)
Cl3	0.03427 (16)	0.63343 (10)	0.12696 (10)	0.0669 (4)
Cl4	0.37255 (14)	0.58671 (9)	0.27270 (8)	0.0493 (3)
Cl5	0.68814 (13)	0.56580 (10)	0.25425 (8)	0.0534 (3)
Cl6	0.41251 (15)	0.39124 (9)	0.22189 (9)	0.0595 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0171 (18)	0.0234 (19)	0.029 (2)	0.0065 (16)	0.0043 (17)	0.0003 (18)
C2	0.030 (2)	0.026 (2)	0.028 (2)	0.0082 (18)	0.0006 (18)	−0.0034 (18)
C3	0.039 (2)	0.024 (2)	0.039 (3)	0.0109 (19)	0.004 (2)	0.002 (2)
C4	0.038 (2)	0.028 (2)	0.033 (2)	0.0155 (19)	0.001 (2)	0.005 (2)
C5	0.026 (2)	0.032 (2)	0.026 (2)	0.0075 (18)	0.0000 (18)	0.0033 (19)
C6	0.0191 (18)	0.027 (2)	0.025 (2)	0.0087 (16)	0.0060 (17)	0.0016 (18)
C7	0.023 (2)	0.029 (2)	0.019 (2)	0.0040 (17)	0.0055 (17)	0.0017 (18)
C8	0.0206 (18)	0.0244 (19)	0.019 (2)	0.0072 (16)	0.0020 (16)	−0.0007 (17)
C9	0.026 (2)	0.026 (2)	0.028 (2)	0.0088 (17)	0.0042 (18)	0.0008 (18)
C10	0.031 (2)	0.032 (2)	0.032 (2)	0.0173 (19)	0.0039 (19)	−0.001 (2)
C11	0.027 (2)	0.051 (3)	0.030 (2)	0.017 (2)	0.0092 (19)	−0.003 (2)
C12	0.028 (2)	0.040 (2)	0.047 (3)	0.008 (2)	0.017 (2)	0.005 (2)
C13	0.034 (2)	0.031 (2)	0.038 (2)	0.0152 (19)	0.013 (2)	0.005 (2)
C14	0.0205 (18)	0.024 (2)	0.024 (2)	0.0103 (16)	0.0040 (17)	0.0028 (17)
C15	0.029 (2)	0.029 (2)	0.035 (3)	−0.0010 (18)	0.013 (2)	−0.002 (2)
C16	0.044 (3)	0.035 (2)	0.036 (3)	0.000 (2)	0.022 (2)	−0.003 (2)
C17	0.042 (3)	0.036 (2)	0.026 (2)	0.009 (2)	0.008 (2)	−0.005 (2)
C18	0.024 (2)	0.038 (2)	0.033 (2)	−0.0012 (19)	0.0001 (19)	−0.010 (2)
C19	0.025 (2)	0.036 (2)	0.028 (2)	0.0038 (18)	0.0074 (19)	−0.001 (2)
C21	0.0218 (19)	0.0234 (19)	0.021 (2)	0.0046 (16)	0.0032 (17)	−0.0012 (17)
C22	0.027 (2)	0.026 (2)	0.031 (2)	0.0049 (17)	0.0047 (18)	0.0049 (19)
C23	0.027 (2)	0.034 (2)	0.033 (2)	0.0111 (18)	0.0033 (19)	0.004 (2)
C24	0.0181 (19)	0.038 (2)	0.035 (2)	0.0096 (18)	0.0020 (18)	0.002 (2)
C25	0.0226 (19)	0.029 (2)	0.030 (2)	0.0029 (17)	0.0066 (18)	0.0001 (19)
C26	0.0205 (18)	0.025 (2)	0.019 (2)	0.0050 (16)	0.0021 (16)	−0.0033 (17)
C27	0.0186 (19)	0.023 (2)	0.024 (2)	0.0031 (16)	0.0090 (18)	0.0015 (18)
C28	0.0180 (18)	0.024 (2)	0.030 (2)	−0.0011 (16)	0.0049 (17)	0.0065 (18)
C29	0.024 (2)	0.038 (2)	0.039 (3)	0.0064 (19)	0.003 (2)	0.007 (2)
C30	0.041 (3)	0.048 (3)	0.038 (3)	0.004 (2)	−0.010 (2)	0.016 (3)
C31	0.051 (3)	0.034 (2)	0.028 (2)	−0.007 (2)	−0.002 (2)	0.001 (2)
C32	0.044 (3)	0.032 (2)	0.034 (3)	0.005 (2)	0.014 (2)	0.006 (2)
C33	0.029 (2)	0.033 (2)	0.029 (2)	0.0077 (19)	0.0060 (19)	0.004 (2)
C34	0.0205 (19)	0.027 (2)	0.033 (2)	0.0085 (17)	0.0078 (18)	0.0058 (19)
C35	0.034 (2)	0.031 (2)	0.038 (3)	0.0008 (19)	0.007 (2)	0.006 (2)
C36	0.045 (3)	0.031 (2)	0.062 (4)	−0.007 (2)	0.014 (3)	0.013 (3)
C37	0.045 (3)	0.047 (3)	0.053 (3)	0.013 (2)	0.024 (3)	0.027 (3)
C38	0.042 (3)	0.049 (3)	0.039 (3)	0.015 (2)	0.018 (2)	0.012 (2)
C39	0.039 (2)	0.031 (2)	0.037 (3)	0.010 (2)	0.014 (2)	0.004 (2)
C40	0.034 (2)	0.040 (3)	0.054 (3)	0.010 (2)	0.015 (2)	0.008 (2)
C41	0.032 (2)	0.051 (3)	0.039 (3)	0.004 (2)	0.003 (2)	0.014 (2)
O1	0.0237 (14)	0.0236 (14)	0.0328 (16)	0.0033 (12)	0.0055 (12)	−0.0002 (12)
O2	0.0271 (14)	0.0214 (13)	0.0417 (17)	0.0092 (12)	0.0154 (13)	0.0070 (13)
O3	0.0217 (14)	0.0252 (14)	0.0337 (16)	0.0037 (12)	−0.0020 (13)	−0.0008 (13)
O4	0.0268 (14)	0.0300 (15)	0.0396 (17)	0.0143 (13)	0.0005 (13)	−0.0042 (14)
O5	0.0237 (14)	0.0220 (14)	0.0438 (18)	0.0020 (12)	−0.0025 (13)	0.0041 (14)
O6	0.0253 (14)	0.0258 (14)	0.0264 (15)	0.0048 (12)	0.0025 (13)	0.0019 (13)
P1	0.0187 (5)	0.0227 (5)	0.0235 (5)	0.0063 (4)	0.0039 (4)	−0.0001 (4)
P2	0.0202 (5)	0.0218 (5)	0.0281 (6)	0.0049 (4)	0.0060 (4)	0.0045 (5)
Cl1	0.0580 (8)	0.0570 (8)	0.0396 (7)	0.0098 (6)	0.0053 (6)	−0.0058 (6)
Cl2	0.0581 (9)	0.0747 (10)	0.1501 (17)	0.0359 (8)	0.0563 (10)	0.0318 (11)
Cl3	0.0503 (8)	0.0416 (7)	0.1024 (12)	0.0064 (6)	0.0021 (8)	0.0011 (8)
Cl4	0.0405 (6)	0.0511 (7)	0.0559 (8)	0.0084 (6)	0.0125 (6)	−0.0021 (6)
Cl5	0.0299 (6)	0.0634 (8)	0.0609 (8)	−0.0005 (6)	0.0080 (6)	0.0048 (7)
Cl6	0.0458 (7)	0.0367 (6)	0.0911 (11)	0.0051 (6)	0.0045 (7)	0.0058 (7)

Geometric parameters (Å, º) top

C1—C2	1.394 (5)	C23—H23	0.9300
C1—C6	1.411 (6)	C24—C25	1.384 (5)
C1—P1	1.816 (4)	C24—H24	0.9300
C2—C3	1.394 (5)	C25—C26	1.392 (5)
C2—H2	0.9300	C25—H25	0.9300
C3—C4	1.368 (6)	C26—C27	1.499 (5)
C3—H3	0.9300	C27—O6	1.210 (4)
C4—C5	1.382 (6)	C27—O5	1.317 (4)
C4—H4	0.9300	C28—C29	1.388 (6)
C5—C6	1.384 (5)	C28—C33	1.398 (5)
C5—H5	0.9300	C28—P2	1.801 (4)
C6—C7	1.501 (5)	C29—C30	1.385 (7)
C7—O4	1.218 (4)	C29—H29	0.9300
C7—O3	1.311 (4)	C30—C31	1.381 (7)
C8—C9	1.387 (5)	C30—H30	0.9300
C8—C13	1.398 (5)	C31—C32	1.377 (6)
C8—P1	1.803 (3)	C31—H31	0.9300
C9—C10	1.373 (5)	C32—C33	1.372 (6)
C9—H9	0.9300	C32—H32	0.9300
C10—C11	1.373 (6)	C33—H33	0.9300
C10—H10	0.9300	C34—C39	1.391 (6)
C11—C12	1.385 (6)	C34—C35	1.391 (6)
C11—H11	0.9300	C34—P2	1.809 (4)
C12—C13	1.385 (5)	C35—C36	1.384 (6)
C12—H12	0.9300	C35—H35	0.9300
C13—H13	0.9300	C36—C37	1.374 (7)
C14—C15	1.388 (5)	C36—H36	0.9300
C14—C19	1.397 (5)	C37—C38	1.371 (7)
C14—P1	1.806 (4)	C37—H37	0.9300
C15—C16	1.394 (6)	C38—C39	1.379 (6)
C15—H15	0.9300	C38—H38	0.9300
C16—C17	1.370 (6)	C39—H39	0.9300
C16—H16	0.9300	C40—Cl3	1.748 (5)
C17—C18	1.371 (6)	C40—Cl2	1.750 (4)
C17—H17	0.9300	C40—Cl1	1.751 (5)
C18—C19	1.383 (6)	C40—H40	0.9800
C18—H18	0.9300	C41—Cl6	1.750 (5)
C19—H19	0.9300	C41—Cl5	1.764 (4)
C21—C22	1.392 (5)	C41—Cl4	1.767 (5)
C21—C26	1.414 (5)	C41—H41	0.9800
C21—P2	1.822 (4)	O1—P1	1.490 (3)
C22—C23	1.398 (5)	O2—P2	1.493 (3)
C22—H22	0.9300	O3—H3A	1.0261
C23—C24	1.376 (6)	O5—H5A	1.0571

C2—C1—C6	118.4 (3)	C24—C25—H25	119.4
C2—C1—P1	119.7 (3)	C26—C25—H25	119.4
C6—C1—P1	121.9 (3)	C25—C26—C21	119.6 (3)
C3—C2—C1	120.4 (4)	C25—C26—C27	119.2 (3)
C3—C2—H2	119.8	C21—C26—C27	121.1 (3)
C1—C2—H2	119.8	O6—C27—O5	124.7 (3)
C4—C3—C2	120.8 (4)	O6—C27—C26	122.0 (3)
C4—C3—H3	119.6	O5—C27—C26	113.3 (3)
C2—C3—H3	119.6	C29—C28—C33	119.6 (4)
C3—C4—C5	119.5 (4)	C29—C28—P2	120.6 (3)
C3—C4—H4	120.2	C33—C28—P2	119.8 (3)
C5—C4—H4	120.2	C30—C29—C28	119.3 (4)
C4—C5—C6	121.0 (4)	C30—C29—H29	120.4
C4—C5—H5	119.5	C28—C29—H29	120.4
C6—C5—H5	119.5	C31—C30—C29	121.0 (4)
C5—C6—C1	119.9 (3)	C31—C30—H30	119.5
C5—C6—C7	119.1 (4)	C29—C30—H30	119.5
C1—C6—C7	120.9 (3)	C32—C31—C30	119.4 (5)
O4—C7—O3	125.2 (3)	C32—C31—H31	120.3
O4—C7—C6	121.0 (3)	C30—C31—H31	120.3
O3—C7—C6	113.8 (3)	C33—C32—C31	120.7 (4)
C9—C8—C13	118.9 (3)	C33—C32—H32	119.6
C9—C8—P1	118.9 (3)	C31—C32—H32	119.6
C13—C8—P1	122.3 (3)	C32—C33—C28	120.0 (4)
C10—C9—C8	120.7 (3)	C32—C33—H33	120.0
C10—C9—H9	119.7	C28—C33—H33	120.0
C8—C9—H9	119.7	C39—C34—C35	118.9 (4)
C11—C10—C9	120.6 (4)	C39—C34—P2	118.1 (3)
C11—C10—H10	119.7	C35—C34—P2	123.0 (3)
C9—C10—H10	119.7	C36—C35—C34	119.8 (4)
C10—C11—C12	119.8 (3)	C36—C35—H35	120.1
C10—C11—H11	120.1	C34—C35—H35	120.1
C12—C11—H11	120.1	C37—C36—C35	120.8 (5)
C13—C12—C11	120.1 (4)	C37—C36—H36	119.6
C13—C12—H12	119.9	C35—C36—H36	119.6
C11—C12—H12	119.9	C38—C37—C36	119.6 (4)
C12—C13—C8	120.0 (4)	C38—C37—H37	120.2
C12—C13—H13	120.0	C36—C37—H37	120.2
C8—C13—H13	120.0	C37—C38—C39	120.6 (4)
C15—C14—C19	118.6 (4)	C37—C38—H38	119.7
C15—C14—P1	116.5 (3)	C39—C38—H38	119.7
C19—C14—P1	124.7 (3)	C38—C39—C34	120.3 (4)
C14—C15—C16	120.9 (4)	C38—C39—H39	119.8
C14—C15—H15	119.6	C34—C39—H39	119.8
C16—C15—H15	119.6	Cl3—C40—Cl2	110.4 (2)
C17—C16—C15	119.1 (4)	Cl3—C40—Cl1	111.2 (2)
C17—C16—H16	120.4	Cl2—C40—Cl1	111.2 (3)
C15—C16—H16	120.4	Cl3—C40—H40	108.0
C16—C17—C18	121.0 (4)	Cl2—C40—H40	108.0
C16—C17—H17	119.5	Cl1—C40—H40	108.0
C18—C17—H17	119.5	Cl6—C41—Cl5	110.2 (3)
C17—C18—C19	120.3 (4)	Cl6—C41—Cl4	109.0 (2)
C17—C18—H18	119.9	Cl5—C41—Cl4	109.8 (2)
C19—C18—H18	119.9	Cl6—C41—H41	109.3
C18—C19—C14	120.1 (3)	Cl5—C41—H41	109.3
C18—C19—H19	120.0	Cl4—C41—H41	109.3
C14—C19—H19	120.0	C7—O3—H3A	108.2
C22—C21—C26	118.2 (3)	C27—O5—H5A	111.4
C22—C21—P2	119.1 (3)	O1—P1—C8	114.21 (16)
C26—C21—P2	122.7 (3)	O1—P1—C14	108.38 (16)
C21—C22—C23	121.4 (3)	C8—P1—C14	106.24 (17)
C21—C22—H22	119.3	O1—P1—C1	113.43 (16)
C23—C22—H22	119.3	C8—P1—C1	106.94 (16)
C24—C23—C22	119.9 (4)	C14—P1—C1	107.20 (17)
C24—C23—H23	120.1	O2—P2—C28	115.51 (17)
C22—C23—H23	120.1	O2—P2—C34	108.77 (15)
C23—C24—C25	119.8 (3)	C28—P2—C34	106.35 (18)
C23—C24—H24	120.1	O2—P2—C21	115.03 (17)
C25—C24—H24	120.1	C28—P2—C21	105.25 (17)
C24—C25—C26	121.2 (3)	C34—P2—C21	105.13 (16)

C6—C1—C2—C3	−2.0 (5)	C29—C30—C31—C32	0.5 (7)
P1—C1—C2—C3	179.5 (3)	C30—C31—C32—C33	−0.3 (6)
C1—C2—C3—C4	2.7 (6)	C31—C32—C33—C28	−0.4 (6)
C2—C3—C4—C5	−0.7 (6)	C29—C28—C33—C32	0.9 (5)
C3—C4—C5—C6	−2.0 (6)	P2—C28—C33—C32	−178.6 (3)
C4—C5—C6—C1	2.7 (5)	C39—C34—C35—C36	0.5 (6)
C4—C5—C6—C7	−173.1 (3)	P2—C34—C35—C36	177.2 (3)
C2—C1—C6—C5	−0.7 (5)	C34—C35—C36—C37	0.9 (7)
P1—C1—C6—C5	177.8 (3)	C35—C36—C37—C38	−0.8 (7)
C2—C1—C6—C7	175.1 (3)	C36—C37—C38—C39	−0.7 (7)
P1—C1—C6—C7	−6.4 (4)	C37—C38—C39—C34	2.2 (6)
C5—C6—C7—O4	137.0 (4)	C35—C34—C39—C38	−2.0 (6)
C1—C6—C7—O4	−38.7 (5)	P2—C34—C39—C38	−178.9 (3)
C5—C6—C7—O3	−41.9 (4)	C9—C8—P1—O1	−14.5 (4)
C1—C6—C7—O3	142.3 (3)	C13—C8—P1—O1	166.0 (3)
C13—C8—C9—C10	1.0 (6)	C9—C8—P1—C14	104.9 (3)
P1—C8—C9—C10	−178.5 (3)	C13—C8—P1—C14	−74.6 (4)
C8—C9—C10—C11	0.6 (6)	C9—C8—P1—C1	−140.9 (3)
C9—C10—C11—C12	−1.1 (7)	C13—C8—P1—C1	39.7 (4)
C10—C11—C12—C13	0.1 (7)	C15—C14—P1—O1	−18.8 (3)
C11—C12—C13—C8	1.5 (7)	C19—C14—P1—O1	156.3 (3)
C9—C8—C13—C12	−1.9 (6)	C15—C14—P1—C8	−141.9 (3)
P1—C8—C13—C12	177.5 (3)	C19—C14—P1—C8	33.1 (3)
C19—C14—C15—C16	−0.6 (6)	C15—C14—P1—C1	104.0 (3)
P1—C14—C15—C16	174.7 (3)	C19—C14—P1—C1	−80.9 (3)
C14—C15—C16—C17	−0.1 (6)	C2—C1—P1—O1	136.3 (3)
C15—C16—C17—C18	1.0 (6)	C6—C1—P1—O1	−42.2 (3)
C16—C17—C18—C19	−1.1 (6)	C2—C1—P1—C8	−96.9 (3)
C17—C18—C19—C14	0.3 (6)	C6—C1—P1—C8	84.6 (3)
C15—C14—C19—C18	0.6 (5)	C2—C1—P1—C14	16.7 (3)
P1—C14—C19—C18	−174.4 (3)	C6—C1—P1—C14	−161.8 (3)
C26—C21—C22—C23	1.2 (6)	C29—C28—P2—O2	12.3 (4)
P2—C21—C22—C23	−178.4 (3)	C33—C28—P2—O2	−168.1 (3)
C21—C22—C23—C24	−2.1 (6)	C29—C28—P2—C34	−108.4 (3)
C22—C23—C24—C25	0.7 (6)	C33—C28—P2—C34	71.1 (3)
C23—C24—C25—C26	1.5 (6)	C29—C28—P2—C21	140.4 (3)
C24—C25—C26—C21	−2.4 (6)	C33—C28—P2—C21	−40.1 (3)
C24—C25—C26—C27	173.1 (4)	C39—C34—P2—O2	55.3 (3)
C22—C21—C26—C25	1.1 (6)	C35—C34—P2—O2	−121.5 (3)
P2—C21—C26—C25	−179.4 (3)	C39—C34—P2—C28	−179.7 (3)
C22—C21—C26—C27	−174.4 (3)	C35—C34—P2—C28	3.5 (4)
P2—C21—C26—C27	5.2 (5)	C39—C34—P2—C21	−68.4 (3)
C25—C26—C27—O6	−140.9 (4)	C35—C34—P2—C21	114.8 (3)
C21—C26—C27—O6	34.5 (5)	C22—C21—P2—O2	−138.7 (3)
C25—C26—C27—O5	36.2 (5)	C26—C21—P2—O2	41.7 (4)
C21—C26—C27—O5	−148.4 (3)	C22—C21—P2—C28	93.0 (3)
C33—C28—C29—C30	−0.7 (6)	C26—C21—P2—C28	−86.6 (3)
P2—C28—C29—C30	178.8 (3)	C22—C21—P2—C34	−19.1 (4)
C28—C29—C30—C31	0.0 (6)	C26—C21—P2—C34	161.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	1.06	1.54	2.578 (3)	166
C41—H41···O6ⁱ	0.98	2.29	3.255 (5)	170
C40—H40···O4ⁱⁱ	0.98	2.55	3.355 (5)	139
O3—H3A···O1ⁱⁱⁱ	1.03	1.56	2.566 (4)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅O₃P·CHCl₃
M_r	441.65
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	8.6828 (9), 13.3850 (14), 17.8678 (18)
α, β, γ (°)	91.572 (12), 98.950 (12), 104.045 (12)
V (Å³)	1985.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.53 × 0.30 × 0.12

Data collection
Diffractometer	Stoe IPDS diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.884, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	15762, 7227, 4039
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.127, 0.97
No. of reflections	7227
No. of parameters	487
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.40

Computer programs: EXPOSE in IPDS Software (Stoe & Cie, 2000), CELL in IPDS Software, INTEGRATE in IPDS Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

C1—P1	1.816 (4)	C27—O6	1.210 (4)
C7—O4	1.218 (4)	C27—O5	1.317 (4)
C7—O3	1.311 (4)	C28—P2	1.801 (4)
C8—P1	1.803 (3)	C34—P2	1.809 (4)
C14—P1	1.806 (4)	O1—P1	1.490 (3)
C21—P2	1.822 (4)	O2—P2	1.493 (3)

O1—P1—C8	114.21 (16)	O2—P2—C28	115.51 (17)
O1—P1—C14	108.38 (16)	O2—P2—C34	108.77 (15)
C8—P1—C14	106.24 (17)	C28—P2—C34	106.35 (18)
O1—P1—C1	113.43 (16)	O2—P2—C21	115.03 (17)
C8—P1—C1	106.94 (16)	C28—P2—C21	105.25 (17)
C14—P1—C1	107.20 (17)	C34—P2—C21	105.13 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	1.06	1.54	2.578 (3)	166
C41—H41···O6ⁱ	0.98	2.29	3.255 (5)	170
C40—H40···O4ⁱⁱ	0.98	2.55	3.355 (5)	139
O3—H3A···O1ⁱⁱⁱ	1.03	1.56	2.566 (4)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y, −z.

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