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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2647.
Published online 2009 October 3. doi:  10.1107/S1600536809038525
PMCID: PMC2971329

Bis(phenyl­phospho­nic) anhydride

Abstract

The asymmetric unit of the title compound, C12H12O5P2, contains four independent mol­ecules, generating two dimers via pairs of inter­molecular O—H(...)O hydrogen bonds, forming R 2 2(8) rings. The two aryl rings of each mol­ecule form dihedral angles of 108.6 (1), 103.2 (1), 12.5 (2) and 8.1 (2)° in the four mol­ecules.

Related literature

For related structural information, see: Kingsley et al. (2001 [triangle]); Bernstein et al. (1995 [triangle]). For syntheses, see: Ruveda et al. (1973 [triangle]); Gallagher & Jenkins (1966 [triangle]); Mikolajczyk (1966 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2647-scheme1.jpg

Experimental

Crystal data

  • C12H12O5P2
  • M r = 298.16
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2647-efi1.jpg
  • a = 5.6510 (7) Å
  • b = 19.3320 (18) Å
  • c = 24.440 (3) Å
  • α = 84.701 (8)°
  • β = 89.192 (8)°
  • γ = 81.687 (7)°
  • V = 2630.6 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 93 K
  • 0.05 × 0.05 × 0.03 mm

Data collection

  • Rigaku Mercury CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2004 [triangle]) T min = 0.983, T max = 0.990
  • 18800 measured reflections
  • 9791 independent reflections
  • 6873 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.142
  • S = 1.07
  • 9791 reflections
  • 694 parameters
  • H-atom parameters constrained
  • Δρmax = 0.69 e Å−3
  • Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku, 2004 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038525/pk2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038525/pk2185Isup2.hkl

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

Acknowledgments

The authors are grateful to the Engineering and Physical Science Research Council (EPSRC, UK) for financial support.

supplementary crystallographic information

Comment

P1P2-disubstituted pyrophosphoric acid has been prepared by the reaction of organophosphorus(V) dichlorides, organophosphorus(III) dichlorides and organothiophosphoryl dichlorides with dimethylsulphoxide (DMSO) (Ruveda et al., 1973; Mikolajczyk, 1966). We report here the synthesis of the title compound by the reaction of succinyl chloride with Woollins' reagent. The x-ray structure reveals that the title compound exists as an independent molecule rather than as a part (mono-anion or anion dimer) of a molecule which has been reported in the literature (Kingsley et al., 2001).

The molecular structure of the title compound is shown in Fig. 1. In the crystal the molecules stacks up the a axis and are connected to one another via pairs of intermolecular O—H···O hydrogen bonds, with R22(8) motif (Bernstein et al., 1995), forming two types of dimers [Table 1]. The four independent molecules have two types of conformations with different dihedral angles between the two benzene rings as described in the abstract.

Experimental

A mixture of succinyl chloride (0.16 g, 1 mmol) and Woollins' reagent (0.27 g, 0.5 mmol) in dry toluene (5 ml) was refluxed for 6 hr. Upon cooling to room temperature the mixture was exposed in the air overnight and purified by silica gel (toluene as eluent) to give diphenyldiphosphonic acid (white paste, 0.168 g, 56%). Colourless crystal was obtained by slow evaporation of chloromethane solution.

Refinement

All H atoms were fixed geometrically (C—H = 0.95 Å, O—H = 0.84 Å) and treated as riding with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(O) of the parent atom.

Figures

Fig. 1.
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Crystal data

C12H12O5P2Z = 8
Mr = 298.16F(000) = 1232
Triclinic, P1Dx = 1.506 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.6510 (7) ÅCell parameters from 8791 reflections
b = 19.3320 (18) Åθ = 1.7–28.5°
c = 24.440 (3) ŵ = 0.34 mm1
α = 84.701 (8)°T = 93 K
β = 89.192 (8)°Prism, colourless
γ = 81.687 (7)°0.05 × 0.05 × 0.03 mm
V = 2630.6 (5) Å3

Data collection

Rigaku Mercury CCD diffractometer9791 independent reflections
Radiation source: rotating anode6873 reflections with I > 2σ(I)
confocal multilayer opticsRint = 0.052
Detector resolution: 0.83 pixels mm-1θmax = 28.5°, θmin = 1.3°
ω scansh = −7→5
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004)k = −24→25
Tmin = 0.983, Tmax = 0.990l = −31→31
18800 measured reflections

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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0599P)2] where P = (Fo2 + 2Fc2)/3
9791 reflections(Δ/σ)max = 0.034
694 parametersΔρmax = 0.69 e Å3
0 restraintsΔρmin = −0.50 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 > 2σ(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
P11.16675 (16)0.61566 (4)0.30579 (3)0.0279 (2)
P20.97193 (17)0.49073 (4)0.35149 (3)0.0290 (2)
P211.01976 (17)0.51094 (4)0.15068 (4)0.0331 (2)
P220.82971 (16)0.38450 (4)0.19407 (3)0.0287 (2)
P410.27280 (14)0.88570 (4)0.03348 (3)0.02070 (19)
P420.48620 (14)0.97558 (4)0.10244 (3)0.02159 (19)
P620.45738 (14)0.12067 (4)0.45418 (3)0.01997 (19)
P610.77543 (14)0.00887 (4)0.40704 (3)0.01895 (19)
O410.0099 (4)0.89512 (11)0.01611 (8)0.0264 (5)
H41−0.07680.91110.04160.040*
O640.4511 (4)0.13924 (10)0.51383 (8)0.0263 (5)
H640.43160.10370.53490.039*
O630.6907 (3)0.06224 (9)0.45239 (8)0.0195 (4)
O430.2930 (4)0.95729 (9)0.06046 (8)0.0216 (5)
O450.7276 (4)0.93941 (10)0.09058 (8)0.0281 (5)
O650.2455 (4)0.09410 (10)0.43377 (8)0.0253 (5)
O611.0438 (4)−0.01264 (10)0.41936 (9)0.0234 (5)
H611.10320.02250.42740.035*
O620.6400 (4)−0.05156 (9)0.41066 (8)0.0230 (5)
O440.4503 (4)1.05595 (10)0.09769 (8)0.0287 (5)
H440.47611.07120.06520.043*
O420.4414 (4)0.87522 (10)−0.01302 (8)0.0260 (5)
O41.1294 (5)0.45037 (12)0.30940 (9)0.0406 (6)
H41.04230.43220.28890.061*
O50.7134 (5)0.50673 (13)0.34033 (11)0.0502 (7)
O20.9874 (4)0.62696 (11)0.26044 (9)0.0357 (6)
O221.2784 (5)0.49518 (14)0.16155 (11)0.0569 (8)
O31.0983 (5)0.55921 (10)0.35369 (9)0.0358 (6)
O210.8651 (5)0.54977 (12)0.19411 (10)0.0442 (7)
H210.94860.57380.21060.066*
O230.8914 (5)0.44308 (10)0.14710 (9)0.0383 (6)
O250.9972 (4)0.37785 (11)0.24119 (9)0.0344 (6)
O240.5660 (4)0.40140 (12)0.20872 (11)0.0446 (7)
H240.49940.43330.18600.067*
O11.4214 (4)0.59276 (12)0.28741 (10)0.0406 (6)
H11.49070.56260.31110.061*
C460.5533 (6)0.77233 (15)0.08698 (14)0.0292 (7)
H460.66810.77940.05900.035*
C660.5408 (6)0.05112 (15)0.30895 (12)0.0250 (7)
H660.43250.01950.32090.030*
C670.5304 (5)0.19544 (14)0.41378 (12)0.0223 (7)
C480.1545 (6)0.97859 (16)0.18590 (13)0.0283 (7)
H480.05601.01200.16200.034*
C420.1633 (6)0.80378 (16)0.12647 (13)0.0298 (8)
H420.01220.83270.12580.036*
C410.3325 (6)0.81587 (15)0.08616 (12)0.0239 (7)
C720.3964 (6)0.22236 (15)0.36675 (12)0.0274 (7)
H720.26180.20170.35720.033*
C470.3815 (6)0.94968 (15)0.16860 (12)0.0230 (7)
C650.5087 (6)0.09054 (16)0.25850 (12)0.0279 (7)
H650.37850.08560.23570.033*
C620.8901 (6)0.10533 (15)0.32413 (12)0.0256 (7)
H621.02150.11030.34660.031*
C610.7339 (5)0.05836 (13)0.34192 (11)0.0185 (6)
C680.7283 (6)0.22652 (14)0.42730 (13)0.0262 (7)
H680.81930.20880.45930.031*
C630.8551 (6)0.14466 (16)0.27425 (13)0.0286 (7)
H630.96110.17700.26250.034*
C490.0736 (7)0.95862 (18)0.23771 (13)0.0359 (8)
H49−0.07980.97880.24950.043*
C71.0219 (6)0.44602 (14)0.41789 (12)0.0245 (7)
C21`0.9653 (6)0.55748 (15)0.08425 (13)0.0285 (7)
C60.9476 (6)0.74039 (15)0.34043 (12)0.0263 (7)
H60.81950.73510.31710.032*
C91.2736 (6)0.36786 (16)0.48229 (13)0.0297 (8)
H91.42270.33980.49130.036*
C280.6996 (6)0.29289 (16)0.12371 (12)0.0276 (7)
H280.55290.32380.11930.033*
C311.1277 (6)0.20238 (16)0.13638 (13)0.0304 (8)
H311.27450.17150.14050.037*
C700.6554 (7)0.30892 (16)0.34780 (14)0.0339 (8)
H700.69840.34790.32530.041*
C50.9271 (6)0.79708 (16)0.37234 (13)0.0300 (8)
H50.78550.83030.37120.036*
C510.4381 (7)0.88049 (19)0.25558 (14)0.0413 (9)
H510.53430.84680.27970.050*
C450.6035 (7)0.71889 (16)0.12873 (15)0.0372 (9)
H450.75480.69010.12990.045*
C101.0901 (6)0.37050 (16)0.52002 (13)0.0313 (8)
H101.11270.34430.55490.038*
C710.4614 (7)0.27951 (15)0.33401 (13)0.0318 (8)
H710.37090.29800.30210.038*
C430.2155 (6)0.74958 (17)0.16757 (14)0.0363 (8)
H430.10030.74130.19520.044*
C500.2131 (8)0.91000 (19)0.27211 (14)0.0433 (10)
H500.15540.89630.30760.052*
C110.8710 (6)0.41162 (16)0.50708 (14)0.0313 (8)
H110.74510.41380.53330.038*
C520.5222 (6)0.90029 (16)0.20367 (13)0.0309 (8)
H520.67590.88000.19220.037*
C640.6649 (6)0.13691 (17)0.24123 (13)0.0313 (8)
H64A0.64180.16360.20660.038*
C270.8736 (6)0.30733 (15)0.15891 (12)0.0244 (7)
C300.9528 (7)0.18844 (17)0.10142 (13)0.0351 (8)
H300.97940.14780.08180.042*
C321.0882 (6)0.26151 (16)0.16542 (13)0.0289 (7)
H321.20730.27070.18970.035*
C250.7334 (7)0.58889 (19)0.00260 (15)0.0468 (10)
H250.60370.5827−0.01990.056*
C240.8800 (7)0.6373 (2)−0.01487 (15)0.0454 (10)
H24A0.85060.6649−0.04900.054*
C120.8367 (6)0.44912 (15)0.45645 (13)0.0286 (7)
H120.68730.47710.44770.034*
C690.7911 (6)0.28281 (15)0.39421 (14)0.0312 (8)
H690.92640.30360.40310.037*
C21.3433 (6)0.69980 (16)0.37591 (13)0.0300 (8)
H21.48490.66660.37730.036*
C11.1543 (6)0.69148 (14)0.34250 (12)0.0251 (7)
C290.7391 (7)0.23369 (17)0.09511 (13)0.0325 (8)
H290.61950.22410.07110.039*
C31.3254 (7)0.75645 (16)0.40719 (13)0.0333 (8)
H31.45570.76250.42950.040*
C81.2425 (6)0.40591 (15)0.43110 (13)0.0275 (7)
H81.37040.40460.40540.033*
C221.1138 (7)0.60564 (18)0.06687 (14)0.0377 (8)
H221.24590.61120.08890.045*
C41.1176 (7)0.80421 (16)0.40597 (13)0.0342 (8)
H4A1.10470.84230.42830.041*
C260.7717 (7)0.54935 (18)0.05210 (15)0.0424 (9)
H260.66710.51680.06430.051*
C440.4361 (7)0.70732 (17)0.16835 (15)0.0381 (9)
H44A0.47130.67010.19650.046*
C231.0706 (7)0.64575 (19)0.01752 (16)0.0466 (10)
H231.17220.67930.00570.056*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0377 (5)0.0226 (4)0.0237 (4)−0.0054 (4)0.0035 (4)−0.0026 (3)
P20.0403 (5)0.0235 (4)0.0237 (4)−0.0074 (4)−0.0037 (4)0.0007 (3)
P210.0417 (6)0.0279 (4)0.0294 (5)−0.0055 (4)−0.0065 (4)0.0009 (4)
P220.0387 (5)0.0236 (4)0.0239 (4)−0.0044 (4)0.0016 (4)−0.0032 (3)
P410.0231 (4)0.0235 (4)0.0162 (4)−0.0043 (3)0.0033 (3)−0.0040 (3)
P420.0244 (4)0.0244 (4)0.0172 (4)−0.0058 (3)0.0048 (3)−0.0056 (3)
P620.0229 (4)0.0200 (4)0.0183 (4)−0.0059 (3)0.0032 (3)−0.0046 (3)
P610.0216 (4)0.0195 (4)0.0168 (4)−0.0051 (3)0.0019 (3)−0.0040 (3)
O410.0235 (12)0.0378 (12)0.0190 (11)−0.0036 (10)0.0042 (9)−0.0095 (9)
O640.0400 (14)0.0227 (10)0.0185 (11)−0.0105 (10)0.0083 (10)−0.0065 (8)
O630.0216 (11)0.0214 (10)0.0162 (10)−0.0035 (8)0.0010 (9)−0.0048 (8)
O430.0249 (11)0.0224 (10)0.0171 (10)−0.0005 (9)0.0000 (9)−0.0038 (8)
O450.0238 (12)0.0365 (12)0.0247 (12)−0.0029 (10)0.0047 (10)−0.0093 (9)
O650.0246 (12)0.0235 (10)0.0299 (12)−0.0087 (9)0.0019 (10)−0.0057 (9)
O610.0214 (11)0.0209 (10)0.0281 (12)−0.0032 (9)−0.0001 (10)−0.0042 (9)
O620.0280 (12)0.0217 (10)0.0209 (11)−0.0089 (9)0.0018 (9)−0.0028 (8)
O440.0443 (14)0.0229 (10)0.0198 (11)−0.0070 (10)0.0105 (11)−0.0047 (9)
O420.0294 (12)0.0305 (11)0.0192 (11)−0.0063 (9)0.0085 (10)−0.0068 (9)
O40.0607 (17)0.0352 (13)0.0265 (13)−0.0060 (12)−0.0034 (12)−0.0066 (10)
O50.0450 (16)0.0572 (16)0.0453 (16)−0.0100 (13)−0.0085 (14)0.0170 (13)
O20.0553 (16)0.0278 (11)0.0262 (12)−0.0121 (11)−0.0001 (12)−0.0047 (9)
O220.0413 (16)0.0653 (18)0.0592 (19)−0.0051 (14)−0.0119 (15)0.0176 (15)
O30.0637 (17)0.0244 (11)0.0213 (12)−0.0140 (11)0.0011 (12)−0.0011 (9)
O210.0661 (19)0.0387 (14)0.0288 (13)−0.0064 (13)−0.0068 (13)−0.0085 (11)
O230.0657 (18)0.0259 (11)0.0246 (12)−0.0122 (11)−0.0035 (12)0.0001 (9)
O250.0498 (15)0.0296 (11)0.0257 (12)−0.0090 (11)0.0002 (11)−0.0082 (9)
O240.0411 (15)0.0400 (14)0.0462 (16)0.0087 (12)0.0074 (13)0.0071 (12)
O10.0449 (15)0.0344 (13)0.0363 (14)0.0090 (11)0.0081 (12)0.0053 (11)
C460.0295 (18)0.0242 (16)0.0339 (19)−0.0038 (14)0.0072 (16)−0.0038 (14)
C660.0250 (17)0.0285 (16)0.0227 (16)−0.0035 (13)0.0023 (14)−0.0092 (13)
C670.0217 (16)0.0264 (15)0.0212 (16)−0.0089 (13)0.0048 (13)−0.0071 (13)
C480.0305 (18)0.0322 (16)0.0239 (17)−0.0082 (14)0.0044 (15)−0.0063 (13)
C420.0291 (18)0.0330 (17)0.0262 (17)−0.0039 (14)0.0052 (15)0.0026 (14)
C410.0269 (17)0.0271 (15)0.0194 (15)−0.0074 (13)0.0032 (14)−0.0058 (13)
C720.0309 (18)0.0265 (15)0.0254 (17)−0.0041 (14)0.0023 (15)−0.0061 (13)
C470.0264 (17)0.0273 (16)0.0168 (15)−0.0063 (13)0.0003 (14)−0.0053 (13)
C650.0284 (18)0.0359 (17)0.0201 (16)−0.0055 (15)−0.0041 (14)−0.0044 (14)
C620.0249 (17)0.0287 (16)0.0240 (16)−0.0053 (13)0.0027 (14)−0.0045 (13)
C610.0215 (16)0.0184 (13)0.0165 (14)−0.0042 (12)0.0039 (13)−0.0044 (11)
C680.0295 (18)0.0224 (15)0.0284 (17)−0.0077 (13)0.0105 (15)−0.0067 (13)
C630.0310 (19)0.0306 (16)0.0243 (17)−0.0098 (14)0.0059 (15)0.0051 (14)
C490.039 (2)0.049 (2)0.0244 (18)−0.0194 (17)0.0098 (16)−0.0122 (16)
C70.0331 (18)0.0184 (14)0.0234 (16)−0.0075 (13)−0.0010 (15)−0.0032 (12)
C21`0.0349 (19)0.0234 (15)0.0265 (17)−0.0026 (14)0.0031 (15)−0.0021 (13)
C60.0299 (18)0.0271 (16)0.0223 (16)−0.0072 (14)0.0008 (14)0.0003 (13)
C90.0313 (19)0.0280 (16)0.0286 (18)−0.0014 (14)−0.0051 (16)−0.0006 (14)
C280.0330 (19)0.0289 (16)0.0220 (16)−0.0107 (14)−0.0020 (15)0.0024 (13)
C310.038 (2)0.0269 (16)0.0247 (17)0.0009 (15)0.0033 (16)−0.0016 (14)
C700.048 (2)0.0230 (16)0.0299 (19)−0.0055 (16)0.0172 (17)−0.0001 (14)
C50.039 (2)0.0265 (16)0.0232 (16)−0.0024 (15)0.0042 (15)−0.0010 (13)
C510.058 (3)0.043 (2)0.0226 (18)−0.0116 (19)−0.0083 (18)0.0052 (16)
C450.038 (2)0.0241 (17)0.045 (2)0.0039 (15)0.0029 (18)0.0065 (16)
C100.040 (2)0.0284 (17)0.0262 (17)−0.0099 (15)−0.0024 (16)0.0001 (14)
C710.047 (2)0.0256 (16)0.0217 (17)−0.0023 (16)0.0080 (16)−0.0010 (14)
C430.037 (2)0.044 (2)0.0286 (19)−0.0104 (17)0.0058 (17)0.0044 (16)
C500.063 (3)0.050 (2)0.0233 (18)−0.029 (2)0.0089 (19)−0.0039 (17)
C110.034 (2)0.0344 (17)0.0294 (18)−0.0136 (15)0.0081 (16)−0.0079 (15)
C520.038 (2)0.0333 (17)0.0213 (17)−0.0047 (15)−0.0045 (15)−0.0010 (14)
C640.036 (2)0.0363 (18)0.0195 (16)−0.0019 (15)0.0002 (15)0.0031 (14)
C270.0296 (18)0.0249 (15)0.0188 (15)−0.0069 (14)0.0007 (14)0.0024 (13)
C300.053 (2)0.0346 (18)0.0213 (17)−0.0129 (17)0.0065 (17)−0.0098 (14)
C320.0335 (19)0.0340 (17)0.0209 (16)−0.0086 (15)0.0015 (15)−0.0052 (14)
C250.052 (3)0.051 (2)0.036 (2)−0.008 (2)−0.014 (2)0.0057 (19)
C240.054 (3)0.050 (2)0.0279 (19)−0.001 (2)0.0039 (19)0.0095 (17)
C120.0298 (18)0.0220 (15)0.0334 (19)−0.0023 (14)−0.0024 (16)−0.0017 (14)
C690.0304 (18)0.0249 (16)0.040 (2)−0.0068 (14)0.0121 (16)−0.0107 (15)
C20.0319 (19)0.0275 (16)0.0306 (18)−0.0090 (14)−0.0019 (16)0.0052 (14)
C10.0348 (19)0.0204 (15)0.0203 (16)−0.0068 (14)0.0042 (15)0.0017 (13)
C290.043 (2)0.0389 (18)0.0201 (16)−0.0192 (17)−0.0004 (16)−0.0026 (14)
C30.043 (2)0.0322 (17)0.0275 (18)−0.0162 (16)−0.0073 (17)0.0026 (15)
C80.0302 (18)0.0246 (15)0.0282 (17)−0.0046 (14)0.0054 (15)−0.0048 (14)
C220.036 (2)0.045 (2)0.034 (2)−0.0106 (17)−0.0005 (17)−0.0026 (16)
C40.057 (2)0.0277 (17)0.0198 (16)−0.0124 (17)0.0004 (17)−0.0028 (14)
C260.050 (2)0.041 (2)0.038 (2)−0.0175 (18)−0.0076 (19)0.0041 (17)
C440.044 (2)0.0288 (17)0.039 (2)−0.0046 (16)0.0024 (18)0.0091 (16)
C230.052 (3)0.048 (2)0.041 (2)−0.0168 (19)0.005 (2)0.0073 (18)

Geometric parameters (Å, °)

P1—O21.492 (2)C63—C641.387 (4)
P1—O11.517 (2)C63—H630.9500
P1—O31.608 (2)C49—C501.367 (5)
P1—C11.780 (3)C49—H490.9500
P2—O51.473 (3)C7—C81.395 (4)
P2—O41.543 (2)C7—C121.397 (4)
P2—O31.598 (2)C21`—C221.376 (5)
P2—C71.773 (3)C21`—C261.391 (5)
P21—O221.472 (3)C6—C11.391 (4)
P21—O211.544 (3)C6—C51.393 (4)
P21—O231.598 (2)C6—H60.9500
P21—C21`1.790 (3)C9—C101.377 (5)
P22—O251.485 (2)C9—C81.391 (4)
P22—O241.524 (3)C9—H90.9500
P22—O231.608 (2)C28—C291.385 (4)
P22—C271.775 (3)C28—C271.390 (4)
P41—O421.482 (2)C28—H280.9500
P41—O411.532 (2)C31—C301.387 (5)
P41—O431.606 (2)C31—C321.390 (4)
P41—C411.776 (3)C31—H310.9500
P42—O451.478 (2)C70—C711.365 (5)
P42—O441.531 (2)C70—C691.392 (5)
P42—O431.606 (2)C70—H700.9500
P42—C471.767 (3)C5—C41.394 (5)
P62—O651.479 (2)C5—H50.9500
P62—O641.532 (2)C51—C501.387 (5)
P62—O631.6101 (19)C51—C521.388 (5)
P62—C671.770 (3)C51—H510.9500
P61—O621.482 (2)C45—C441.370 (5)
P61—O611.540 (2)C45—H450.9500
P61—O631.6049 (19)C10—C111.395 (5)
P61—C611.780 (3)C10—H100.9500
O41—H410.8400C71—H710.9500
O64—H640.8400C43—C441.388 (5)
O61—H610.8400C43—H430.9500
O44—H440.8400C50—H500.9500
O4—H40.8400C11—C121.377 (4)
O21—H210.8400C11—H110.9500
O24—H240.8400C52—H520.9500
O1—H10.8400C64—H64A0.9500
C46—C451.385 (4)C27—C321.396 (4)
C46—C411.400 (4)C30—C291.387 (5)
C46—H460.9500C30—H300.9500
C66—C651.388 (4)C32—H320.9500
C66—C611.396 (4)C25—C261.372 (5)
C66—H660.9500C25—C241.373 (5)
C67—C681.401 (4)C25—H250.9500
C67—C721.402 (4)C24—C231.383 (5)
C48—C491.381 (4)C24—H24A0.9500
C48—C471.399 (4)C12—H120.9500
C48—H480.9500C69—H690.9500
C42—C431.385 (4)C2—C31.383 (4)
C42—C411.391 (4)C2—C11.390 (4)
C42—H420.9500C2—H20.9500
C72—C711.393 (4)C29—H290.9500
C72—H720.9500C3—C41.384 (5)
C47—C521.388 (4)C3—H30.9500
C65—C641.382 (5)C8—H80.9500
C65—H650.9500C22—C231.377 (5)
C62—C631.377 (4)C22—H220.9500
C62—C611.393 (4)C4—H4A0.9500
C62—H620.9500C26—H260.9500
C68—C691.380 (4)C44—H44A0.9500
C68—H680.9500C23—H230.9500
O2—P1—O1114.15 (14)C8—C7—C12120.0 (3)
O2—P1—O3111.31 (14)C8—C7—P2120.3 (2)
O1—P1—O3108.61 (13)C12—C7—P2119.7 (2)
O2—P1—C1111.27 (14)C22—C21`—C26120.1 (3)
O1—P1—C1109.97 (15)C22—C21`—P21117.7 (3)
O3—P1—C1100.69 (13)C26—C21`—P21122.1 (3)
O5—P2—O4117.45 (16)C1—C6—C5120.4 (3)
O5—P2—O3113.31 (14)C1—C6—H6119.8
O4—P2—O3101.76 (14)C5—C6—H6119.8
O5—P2—C7110.02 (15)C10—C9—C8120.5 (3)
O4—P2—C7109.34 (14)C10—C9—H9119.7
O3—P2—C7103.89 (13)C8—C9—H9119.7
O22—P21—O21116.66 (17)C29—C28—C27120.3 (3)
O22—P21—O23114.18 (15)C29—C28—H28119.9
O21—P21—O23101.71 (14)C27—C28—H28119.9
O22—P21—C21`110.40 (16)C30—C31—C32120.0 (3)
O21—P21—C21`109.76 (14)C30—C31—H31120.0
O23—P21—C21`103.02 (14)C32—C31—H31120.0
O25—P22—O24115.00 (15)C71—C70—C69121.2 (3)
O25—P22—O23111.24 (14)C71—C70—H70119.4
O24—P22—O23108.06 (13)C69—C70—H70119.4
O25—P22—C27110.61 (13)C6—C5—C4118.9 (3)
O24—P22—C27109.15 (15)C6—C5—H5120.5
O23—P22—C27101.96 (13)C4—C5—H5120.5
O42—P41—O41113.20 (12)C50—C51—C52119.8 (3)
O42—P41—O43111.81 (12)C50—C51—H51120.1
O41—P41—O43102.90 (11)C52—C51—H51120.1
O42—P41—C41110.80 (13)C44—C45—C46120.4 (3)
O41—P41—C41110.44 (14)C44—C45—H45119.8
O43—P41—C41107.30 (12)C46—C45—H45119.8
O45—P42—O44117.30 (13)C9—C10—C11120.0 (3)
O45—P42—O43110.83 (11)C9—C10—H10120.0
O44—P42—O43103.69 (11)C11—C10—H10120.0
O45—P42—C47113.03 (13)C70—C71—C72119.9 (3)
O44—P42—C47105.64 (13)C70—C71—H71120.1
O43—P42—C47105.29 (13)C72—C71—H71120.1
O65—P62—O64117.28 (13)C42—C43—C44119.9 (3)
O65—P62—O63110.48 (11)C42—C43—H43120.0
O64—P62—O63103.31 (11)C44—C43—H43120.0
O65—P62—C67113.19 (13)C49—C50—C51120.5 (3)
O64—P62—C67106.07 (13)C49—C50—H50119.8
O63—P62—C67105.44 (12)C51—C50—H50119.8
O62—P61—O61113.12 (11)C12—C11—C10120.2 (3)
O62—P61—O63112.18 (11)C12—C11—H11119.9
O61—P61—O63103.07 (11)C10—C11—H11119.9
O62—P61—C61111.08 (13)C47—C52—C51120.0 (3)
O61—P61—C61110.42 (13)C47—C52—H52120.0
O63—P61—C61106.52 (11)C51—C52—H52120.0
P41—O41—H41109.5C65—C64—C63120.3 (3)
P62—O64—H64109.5C65—C64—H64A119.9
P61—O63—P62130.24 (13)C63—C64—H64A119.9
P41—O43—P42130.60 (12)C28—C27—C32119.5 (3)
P61—O61—H61109.5C28—C27—P22120.8 (2)
P42—O44—H44109.5C32—C27—P22119.7 (2)
P2—O4—H4109.5C29—C30—C31120.1 (3)
P2—O3—P1131.31 (15)C29—C30—H30120.0
P21—O21—H21109.5C31—C30—H30120.0
P21—O23—P22130.90 (15)C31—C32—C27120.0 (3)
P22—O24—H24109.5C31—C32—H32120.0
P1—O1—H1109.5C27—C32—H32120.0
C45—C46—C41119.7 (3)C26—C25—C24120.9 (4)
C45—C46—H46120.2C26—C25—H25119.6
C41—C46—H46120.2C24—C25—H25119.6
C65—C66—C61119.3 (3)C25—C24—C23119.6 (3)
C65—C66—H66120.4C25—C24—H24A120.2
C61—C66—H66120.4C23—C24—H24A120.2
C68—C67—C72119.4 (3)C11—C12—C7119.9 (3)
C68—C67—P62120.3 (2)C11—C12—H12120.0
C72—C67—P62120.3 (2)C7—C12—H12120.0
C49—C48—C47120.0 (3)C68—C69—C70119.7 (3)
C49—C48—H48120.0C68—C69—H69120.2
C47—C48—H48120.0C70—C69—H69120.2
C43—C42—C41119.9 (3)C3—C2—C1120.1 (3)
C43—C42—H42120.0C3—C2—H2120.0
C41—C42—H42120.0C1—C2—H2120.0
C42—C41—C46119.6 (3)C2—C1—C6119.8 (3)
C42—C41—P41121.0 (2)C2—C1—P1120.5 (2)
C46—C41—P41119.4 (2)C6—C1—P1119.6 (2)
C71—C72—C67119.8 (3)C28—C29—C30120.1 (3)
C71—C72—H72120.1C28—C29—H29119.9
C67—C72—H72120.1C30—C29—H29119.9
C52—C47—C48119.4 (3)C2—C3—C4120.0 (3)
C52—C47—P42120.5 (2)C2—C3—H3120.0
C48—C47—P42120.1 (2)C4—C3—H3120.0
C64—C65—C66120.4 (3)C9—C8—C7119.4 (3)
C64—C65—H65119.8C9—C8—H8120.3
C66—C65—H65119.8C7—C8—H8120.3
C63—C62—C61120.4 (3)C21`—C22—C23119.9 (3)
C63—C62—H62119.8C21`—C22—H22120.1
C61—C62—H62119.8C23—C22—H22120.1
C62—C61—C66119.8 (3)C3—C4—C5120.7 (3)
C62—C61—P61120.4 (2)C3—C4—H4A119.6
C66—C61—P61119.8 (2)C5—C4—H4A119.6
C69—C68—C67120.0 (3)C25—C26—C21`119.3 (4)
C69—C68—H68120.0C25—C26—H26120.3
C67—C68—H68120.0C21`—C26—H26120.3
C62—C63—C64119.8 (3)C45—C44—C43120.4 (3)
C62—C63—H63120.1C45—C44—H44A119.8
C64—C63—H63120.1C43—C44—H44A119.8
C50—C49—C48120.4 (3)C22—C23—C24120.2 (4)
C50—C49—H49119.8C22—C23—H23119.9
C48—C49—H49119.8C24—C23—H23119.9
O62—P61—O63—P62−77.15 (18)O5—P2—C7—C12−18.7 (3)
O61—P61—O63—P62160.86 (16)O4—P2—C7—C12−149.0 (2)
C61—P61—O63—P6244.6 (2)O3—P2—C7—C12102.9 (3)
O65—P62—O63—P6139.8 (2)O22—P21—C21`—C22−36.8 (3)
O64—P62—O63—P61166.04 (16)O21—P21—C21`—C2293.2 (3)
C67—P62—O63—P61−82.84 (19)O23—P21—C21`—C22−159.1 (3)
O42—P41—O43—P42−78.49 (19)O22—P21—C21`—C26147.2 (3)
O41—P41—O43—P42159.72 (16)O21—P21—C21`—C26−82.8 (3)
C41—P41—O43—P4243.2 (2)O23—P21—C21`—C2624.9 (3)
O45—P42—O43—P4136.2 (2)C1—C6—C5—C40.5 (5)
O44—P42—O43—P41162.96 (16)C41—C46—C45—C441.7 (5)
C47—P42—O43—P41−86.29 (19)C8—C9—C10—C11−0.1 (5)
O5—P2—O3—P1−73.7 (2)C69—C70—C71—C720.1 (5)
O4—P2—O3—P153.4 (2)C67—C72—C71—C700.1 (5)
C7—P2—O3—P1166.9 (2)C41—C42—C43—C44−0.2 (5)
O2—P1—O3—P234.0 (2)C48—C49—C50—C510.5 (5)
O1—P1—O3—P2−92.5 (2)C52—C51—C50—C49−0.2 (5)
C1—P1—O3—P2152.0 (2)C9—C10—C11—C120.6 (5)
O22—P21—O23—P2271.7 (3)C48—C47—C52—C51−0.6 (5)
O21—P21—O23—P22−54.9 (2)P42—C47—C52—C51179.9 (3)
C21`—P21—O23—P22−168.6 (2)C50—C51—C52—C470.3 (5)
O25—P22—O23—P21−26.3 (3)C66—C65—C64—C63−0.2 (5)
O24—P22—O23—P21100.8 (2)C62—C63—C64—C650.8 (5)
C27—P22—O23—P21−144.3 (2)C29—C28—C27—C32−0.3 (5)
O65—P62—C67—C68−179.3 (2)C29—C28—C27—P22177.9 (2)
O64—P62—C67—C6850.8 (3)O25—P22—C27—C28162.1 (2)
O63—P62—C67—C68−58.4 (3)O24—P22—C27—C2834.6 (3)
O65—P62—C67—C72−1.8 (3)O23—P22—C27—C28−79.5 (3)
O64—P62—C67—C72−131.8 (2)O25—P22—C27—C32−19.7 (3)
O63—P62—C67—C72119.1 (2)O24—P22—C27—C32−147.2 (2)
C43—C42—C41—C461.0 (5)O23—P22—C27—C3298.7 (3)
C43—C42—C41—P41−179.1 (3)C32—C31—C30—C290.4 (5)
C45—C46—C41—C42−1.7 (5)C30—C31—C32—C27−0.7 (5)
C45—C46—C41—P41178.4 (3)C28—C27—C32—C310.7 (5)
O42—P41—C41—C42−162.5 (2)P22—C27—C32—C31−177.5 (2)
O41—P41—C41—C42−36.3 (3)C26—C25—C24—C230.8 (6)
O43—P41—C41—C4275.1 (3)C10—C11—C12—C70.0 (5)
O42—P41—C41—C4617.4 (3)C8—C7—C12—C11−1.1 (4)
O41—P41—C41—C46143.6 (2)P2—C7—C12—C11176.7 (2)
O43—P41—C41—C46−105.0 (3)C67—C68—C69—C700.7 (4)
C68—C67—C72—C710.1 (4)C71—C70—C69—C68−0.5 (5)
P62—C67—C72—C71−177.4 (2)C3—C2—C1—C60.3 (5)
C49—C48—C47—C520.9 (5)C3—C2—C1—P1−175.6 (2)
C49—C48—C47—P42−179.6 (2)C5—C6—C1—C2−1.1 (5)
O45—P42—C47—C520.2 (3)C5—C6—C1—P1174.8 (2)
O44—P42—C47—C52−129.3 (3)O2—P1—C1—C2−162.5 (2)
O43—P42—C47—C52121.3 (3)O1—P1—C1—C2−35.1 (3)
O45—P42—C47—C48−179.3 (2)O3—P1—C1—C279.4 (3)
O44—P42—C47—C4851.2 (3)O2—P1—C1—C621.6 (3)
O43—P42—C47—C48−58.2 (3)O1—P1—C1—C6149.1 (2)
C61—C66—C65—C64−0.5 (4)O3—P1—C1—C6−96.4 (3)
C63—C62—C61—C660.0 (4)C27—C28—C29—C300.0 (5)
C63—C62—C61—P61−178.7 (2)C31—C30—C29—C280.0 (5)
C65—C66—C61—C620.6 (4)C1—C2—C3—C41.1 (5)
C65—C66—C61—P61179.3 (2)C10—C9—C8—C7−1.1 (5)
O62—P61—C61—C62−163.0 (2)C12—C7—C8—C91.6 (4)
O61—P61—C61—C62−36.6 (3)P2—C7—C8—C9−176.2 (2)
O63—P61—C61—C6274.6 (2)C26—C21`—C22—C23−0.1 (5)
O62—P61—C61—C6618.3 (3)P21—C21`—C22—C23−176.1 (3)
O61—P61—C61—C66144.7 (2)C2—C3—C4—C5−1.7 (5)
O63—P61—C61—C66−104.1 (2)C6—C5—C4—C30.9 (5)
C72—C67—C68—C69−0.5 (4)C24—C25—C26—C21`−1.5 (6)
P62—C67—C68—C69177.0 (2)C22—C21`—C26—C251.1 (5)
C61—C62—C63—C64−0.7 (4)P21—C21`—C26—C25177.0 (3)
C47—C48—C49—C50−0.8 (5)C46—C45—C44—C43−0.9 (5)
O5—P2—C7—C8159.2 (2)C42—C43—C44—C450.1 (5)
O4—P2—C7—C828.8 (3)C21`—C22—C23—C24−0.6 (6)
O3—P2—C7—C8−79.2 (3)C25—C24—C23—C220.3 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O41—H41···O45i0.841.692.530 (3)175
O64—H64···O62ii0.841.672.488 (3)163
O61—H61···O65iii0.841.722.551 (3)171
O4—H4···O250.841.692.464 (3)153
O21—H21···O20.841.702.472 (3)152
O24—H24···O22i0.841.672.464 (3)156
O1—H1···O5iii0.841.662.456 (3)157

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2185).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Gallagher, M. J. & Jenkins, I. D. (1966). J. Chem. Soc. C, pp. 2176–2181.
  • Kingsley, S., Vij, A. & Chandrasekhar, V. (2001). Inorg. Chem.40, 6057–6060. [PubMed]
  • Mikolajczyk, M. (1966). Angew. Chem. Int. Ed. Engl 5, 419.
  • Rigaku (2004). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Ruveda, M. A., Zerba, E. N. & Aldao, E. M. M. (1973). Tetrahedron, 29, 585–587.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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