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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o243
https://doi.org/10.1107/S160053680706463X

Tetra­phenyl­phospho­nium hydrogen oxalate

Philip A. W. Dean,a* Donald C. Craig,b Marcia L. Scudderb and Ian G. Danceb

aDepartment of Chemistry, University of Western Ontario, London, Ontario, N6A 5B7, Canada, and bSchool of Chemistry, University of New South Wales, Sydney, 2052, Australia
*Correspondence e-mail: pawdean@uwo.ca

(Received 22 November 2007; accepted 30 November 2007; online 12 December 2007)

In the title compound, C24H20P+·C2HO4−, two symmetry-independent ion pairs are present. The cations aggregate into puckered sheets via zigzag infinite chains of sixfold phenyl embraces and parallel fourfold phenyl embraces, while the anions form hydrogen-bonded chains between the sheets of cations. In the two independent oxalate anions, the angles between the normals to the two least-squares carboxyl­ate COO planes are unusually large, viz. 72.5 (1) and 82.1 (1)°.

Related literature

For a related investigation of the packing of Ph4P+ ions in the presence of differently shaped and/or charged anions, see: Dean et al. (2004[Dean, P. A. W., Jennings, M., Houle, T. M., Craig, D. C., Dance, I. G., Hook, J. M. & Scudder, M. L. (2004). CrystEngComm, 6, 543-548.]). For a discussion of phenyl braces, see: Scudder & Dance (1998[Scudder, M. L. & Dance, I. G. (1998). J. Chem. Soc. Dalton Trans. pp. 3167-3175.]).

For related literature, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); Braga et al. (2002[Braga, D., Eckert, M., Fraccastoro, M., Maini, L., Grepioni, F., Canaschi, A. & Sessoli, R. (2002). New J. Chem. 26, 1280-1286.]); Chandra et al. (1998[Chandra, N. R., Prabu, M. M., Venkatraman, J., Suresh, S. & Vijayan, M. (1998). Acta Cryst. B54, 257-263.]); Periasamy et al. (2004[Periasamy, M., Reddy, M. M. & Anwar, S. (2004). Tetrahedron Asymmetry, 15, 1809-1812.]); Ramanaiah et al. (1999[Ramanaiah, K. C. V., Zhu, N., Klein-Stevens, C. & Trudell, M. L. (1999). Org. Lett. 1, 1439-1441.]); Rodrigues et al. (2001[Rodrigues, V. H., Paixão, J. A., Costa, M. M. R. R. & Matos Beja, A. (2001). Acta Cryst. C57, 213-215.]).

[Scheme 1]

Experimental

Crystal data

  • C24H20P+·C2HO4−

  • Mr = 428.4

  • Triclinic, [P \overline 1]

  • a = 9.517 (5) Å

  • b = 10.860 (7) Å

  • c = 22.032 (9) Å

  • α = 78.49 (3)°

  • β = 88.37 (2)°

  • γ = 75.13 (3)°

  • V = 2156 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.15 mm−1

  • T = 294 K

  • 0.25 × 0.20 × 0.05 mm
Data collection

  • Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 8001 measured reflections

  • 7564 independent reflections

  • 4017 reflections with I > 2σ(I)

  • Rint = 0.019

  • 1 standard reflection frequency: 30 min intensity decay: none
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.053

  • S = 1.35

  • 4017 reflections

  • 367 parameters

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.91 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O4C—H1O4C⋯O1D 1.00 1.51 2.505 (2) 180
O4D—H1O4D⋯O1Ci 1.00 1.50 2.500 (2) 180
Symmetry code: (i) x, y-1, z.

Data collection: CAD-4 (Schagen et al., 1989[Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Manual. Version 5.0. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: RAELS (Rae, 2000[Rae, A. D. (2000). RAELS. Australian National University, Canberra, Australia.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) and CrystalMaker (CrystalMaker Software, 2005[CrystalMaker Software (2005). CrystalMaker. CrystalMaker Software, Bicester, Oxfordshire, England, www.CrystalMaker.co.uk.]); software used to prepare material for publication: local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680706463X/ln2012sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706463X/ln2012Isup2.hkl

checkCIF report


Comment top

The structure of Ph4P+ HC2O4- was determined as part of a series investigating the packing of Ph4P+ ions in the presence of differently shaped and/or charged anions (Dean et al., 2004). The structure contains recognizable Ph4P+ and HC2O4- ions, each in two crystallographically distinct forms (Figure 1). The PPh4+ cations, A and B, each aggregate via zigzag infinite chains of sixfold phenyl embraces (ZZI6PE) (Scudder & Dance, 1998) propagating parallel to the b axis. Within the P1A-containing chains, alternating P···P distances of 6.476 (1) and 6.609 (1) Å are found, and the P···P···P angle is 112.2 (1)°. The corresponding metrics in the chains containing P1B are 6.093 (1) and 6.684 (1) Å and 116.3 (1)°. The ZZI6PE chains are linked into puckered sheets, lying parallel to bc, through parallel fourfold phenyl embraces (P4PE) (Scudder & Dance, 1998) with a P1A···P1B distance of 8.072 (1) Å. The two P1A···P1A···P1B angles are 99.6 (1) and 144.3 (1)°, while the two P1B···P1B···P1A angles are 99.5 (1) and 140.9 (1)°.

Between the sheets of PPh4+ cations, hydrogen-bonded chains of alternating crystallographically independent HC2O4- anions, C and D, run parallel to the b axis (Figure 2). The distances between the O atoms involved in the hydrogen bonds are 2.505 (2) and 2.500 (2) Å for O4C···O1D and O4D···.O1C, respectively (Table 1). For the two independent molecules, the angle between the normals to the least squares planes defined by the two carboxylate COO groups are 72.5 (1) and 82.1 (1)°, for anions C and D, respectively. A search of the Cambridge Structural Database (CSD V5.27 2006, Allen, 2002) for structures containing uncoordinated H2C2O4 or HC2O4- revealed that while there is a full spread of angles between these normals, from 0–90°, the preference is for an angle near to, or exactly, 0°. Out of 156 hits, in only 6 does this angle exceed 65° [CSD refcode AHETAI, 85.6° (Braga et al., 2002); AHESUB, 69.5° (Braga et al., 2002); BEYDAL, 80.3° (Periasamy, et al., 2004); GUKYEQ, 70.2° (Rodrigues et al., 2001); NOSXAU, 87.0° (Chandra et al., 1998); XEHZEP, 75.6° (Ramanaiah et al., 1999)].

Related literature top

For a related investigation of the packing of Ph4P+ ions in the presence of differently shaped and/or charged anions, see: Dean et al. (2004). For a discussion of phenyl braces, see: Scudder & Dance (1998).

For related literature, see: Allen (2002); Braga et al. (2002); Chandra et al. (1998); Periasamy et al. (2004); Ramanaiah et al. (1999); Rodrigues et al. (2001).

Experimental top

Ph4P+ HC2O4- was the only crystalline product isolated from an attempt to synthesize (Ph4P+)2 C2O42- in crystalline form. Thus, Ph4P+ Br- (0.859 g, 2.05 mmol) and Ag2C2O4 (0.380 g, 1.25 mmol) were stirred together at ambient laboratory temperature in ca 15 ml of Me2CO in a foil-wrapped vial. After 2 days, the precipitate was allowed to settle and the mother liquor was separated by decantation. Slow evaporation of the mother liquor for 6 days at ambient laboratory temperature, led to a small number of colourless plate-like crystals. The data crystal was selected from these. No further formation of X-ray quality crystals occurred on further evaporation of the mother liquor. The compound Ph4P+ HC2O4- is presumably a hydrolysis product of the intended (Ph4P+)2 C2O42-.

Refinement top

The carbon atoms of the cations were refined anisotropcally with 12-parameter TL rigid-body thermal parameters with their centres of libration at the appropriate P atom used for each phenyl ring. The remainimg non-hydrogen atoms were refined with single atom anisotropic thermal parameters. Hydrogen atoms were included in positions calculated each cycle (C—H = 1.00 Å), and their thermal motions were either included in the appropriate rigid group or assigned equal to Ueq of their bonded atom.

Structure description top

The structure of Ph4P+ HC2O4- was determined as part of a series investigating the packing of Ph4P+ ions in the presence of differently shaped and/or charged anions (Dean et al., 2004). The structure contains recognizable Ph4P+ and HC2O4- ions, each in two crystallographically distinct forms (Figure 1). The PPh4+ cations, A and B, each aggregate via zigzag infinite chains of sixfold phenyl embraces (ZZI6PE) (Scudder & Dance, 1998) propagating parallel to the b axis. Within the P1A-containing chains, alternating P···P distances of 6.476 (1) and 6.609 (1) Å are found, and the P···P···P angle is 112.2 (1)°. The corresponding metrics in the chains containing P1B are 6.093 (1) and 6.684 (1) Å and 116.3 (1)°. The ZZI6PE chains are linked into puckered sheets, lying parallel to bc, through parallel fourfold phenyl embraces (P4PE) (Scudder & Dance, 1998) with a P1A···P1B distance of 8.072 (1) Å. The two P1A···P1A···P1B angles are 99.6 (1) and 144.3 (1)°, while the two P1B···P1B···P1A angles are 99.5 (1) and 140.9 (1)°.

Between the sheets of PPh4+ cations, hydrogen-bonded chains of alternating crystallographically independent HC2O4- anions, C and D, run parallel to the b axis (Figure 2). The distances between the O atoms involved in the hydrogen bonds are 2.505 (2) and 2.500 (2) Å for O4C···O1D and O4D···.O1C, respectively (Table 1). For the two independent molecules, the angle between the normals to the least squares planes defined by the two carboxylate COO groups are 72.5 (1) and 82.1 (1)°, for anions C and D, respectively. A search of the Cambridge Structural Database (CSD V5.27 2006, Allen, 2002) for structures containing uncoordinated H2C2O4 or HC2O4- revealed that while there is a full spread of angles between these normals, from 0–90°, the preference is for an angle near to, or exactly, 0°. Out of 156 hits, in only 6 does this angle exceed 65° [CSD refcode AHETAI, 85.6° (Braga et al., 2002); AHESUB, 69.5° (Braga et al., 2002); BEYDAL, 80.3° (Periasamy, et al., 2004); GUKYEQ, 70.2° (Rodrigues et al., 2001); NOSXAU, 87.0° (Chandra et al., 1998); XEHZEP, 75.6° (Ramanaiah et al., 1999)].

For a related investigation of the packing of Ph4P+ ions in the presence of differently shaped and/or charged anions, see: Dean et al. (2004). For a discussion of phenyl braces, see: Scudder & Dance (1998).

For related literature, see: Allen (2002); Braga et al. (2002); Chandra et al. (1998); Periasamy et al. (2004); Ramanaiah et al. (1999); Rodrigues et al. (2001).

Computing details top

Data collection: CAD-4 (Schagen et al., 1989); cell refinement: CAD-4; data reduction: Local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEPII (Johnson, 1976) and CrystalMaker (CrystalMaker Software, 2005); software used to prepare material for publication: Local programs.

Figures top
[Figure 1] Fig. 1. A view of the two independent Ph4P+ cations and HC2O4- anions, showing the labelling of the non-H atoms. Thermal ellipsoids are shown at the 50% probability levels.
[Figure 2] Fig. 2. Projection down the a axis of the lattice of Ph4P+HC2O4-, showing the hydrogen-bonded chains of HC2O4- anions (labelled OxC and OxD) propagating parallel to the b axis. The zigzag chains of cations are also evident. H atoms have been omitted for clarity. Symmetry operators: (i) 1 - x, 1 - y, 1 - z; (ii) 1 - x, 1 - y, -z; (iii) -x, 1 - y, 1 - z; (iv) x, 1 + y, z; v -x, -y, 1 - z.
Tetraphenylphosphonium hydrogen oxalate top
Crystal data top
C24H20P+·C2HO4−Z = 4
Mr = 428.4F(000) = 896.0
Triclinic, P1Dx = 1.32 Mg m−3
a = 9.517 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.860 (7) ÅCell parameters from 10 reflections
c = 22.032 (9) Åθ = 10–11°
α = 78.49 (3)°µ = 0.15 mm−1
β = 88.37 (2)°T = 294 K
γ = 75.13 (3)°Plate, colourless
V = 2156 (2) Å30.25 × 0.20 × 0.05 mm
Data collection top
Nonius CAD-4
diffractometer		θmax = 25°
ω–2θ scansh = −11→11
8001 measured reflectionsk = 0→12
7564 independent reflectionsl = −26→26
4017 reflections with I > 2σ(I)1 standard reflections every 30 min
Rint = 0.019 intensity decay: none
Refinement top
Refinement on F0 restraints
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.053 w = 1/[σ2(F) + 0.0004F2]
S = 1.35(Δ/σ)max = 0.005
4017 reflectionsΔρmax = 0.53 e Å−3
367 parametersΔρmin = −0.91 e Å−3
Crystal data top
C24H20P+·C2HO4−γ = 75.13 (3)°
Mr = 428.4V = 2156 (2) Å3
Triclinic, P1Z = 4
a = 9.517 (5) ÅMo Kα radiation
b = 10.860 (7) ŵ = 0.15 mm−1
c = 22.032 (9) ÅT = 294 K
α = 78.49 (3)°0.25 × 0.20 × 0.05 mm
β = 88.37 (2)°
Data collection top
Nonius CAD-4
diffractometer		Rint = 0.019
8001 measured reflections1 standard reflections every 30 min
7564 independent reflections intensity decay: none
4017 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.053H-atom parameters constrained
S = 1.35Δρmax = 0.53 e Å−3
4017 reflectionsΔρmin = −0.91 e Å−3
367 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P1A0.56052 (10)0.26506 (10)0.42012 (5)0.0398 (3)
C1A0.3737 (4)0.2877 (4)0.4413 (2)0.043 (1)
C2A0.3320 (4)0.2991 (4)0.5014 (2)0.056 (1)
C3A0.1873 (4)0.3192 (5)0.5165 (2)0.077 (2)
C4A0.0856 (5)0.3254 (5)0.4721 (2)0.083 (2)
C5A0.1249 (4)0.3135 (5)0.4121 (2)0.072 (1)
C6A0.2688 (4)0.2955 (4)0.3967 (2)0.052 (1)
C7A0.6704 (4)0.2379 (4)0.4888 (2)0.0432 (9)
C8A0.7397 (4)0.1130 (4)0.5184 (2)0.0572 (9)
C9A0.8159 (5)0.0945 (5)0.5737 (2)0.073 (1)
C10A0.8248 (5)0.2010 (5)0.5978 (2)0.072 (1)
C11A0.7578 (4)0.3250 (5)0.5680 (2)0.065 (1)
C12A0.6801 (4)0.3443 (4)0.5135 (2)0.0519 (8)
C13A0.6152 (4)0.1255 (4)0.3853 (2)0.043 (1)
C14A0.5276 (5)0.0419 (4)0.3840 (2)0.060 (1)
C15A0.5776 (5)−0.0671 (4)0.3577 (2)0.075 (1)
C16A0.7157 (5)−0.0936 (4)0.3343 (2)0.069 (1)
C17A0.8027 (5)−0.0111 (4)0.3357 (2)0.062 (1)
C18A0.7541 (4)0.0986 (4)0.3604 (2)0.051 (1)
C19A0.5877 (4)0.4074 (3)0.3689 (2)0.0393 (8)
C20A0.7254 (4)0.4290 (4)0.3649 (2)0.0523 (8)
C21A0.7506 (5)0.5365 (4)0.3247 (2)0.0647 (8)
C22A0.6379 (5)0.6222 (4)0.2887 (2)0.062 (1)
C23A0.5005 (5)0.6014 (4)0.2915 (2)0.060 (1)
C24A0.4742 (4)0.4935 (4)0.3315 (2)0.0495 (8)
P1B0.55487 (11)0.69137 (10)0.07479 (5)0.0416 (3)
C1B0.3754 (4)0.7491 (4)0.0402 (2)0.046 (1)
C2B0.2553 (4)0.7702 (4)0.0779 (2)0.060 (1)
C3B0.1184 (5)0.8189 (5)0.0504 (3)0.079 (1)
C4B0.0997 (5)0.8412 (5)−0.0126 (3)0.083 (2)
C5B0.2181 (5)0.8167 (4)−0.0501 (2)0.073 (2)
C6B0.3569 (4)0.7707 (4)−0.0243 (2)0.056 (1)
C7B0.6838 (4)0.6713 (4)0.0148 (2)0.045 (1)
C8B0.7547 (4)0.5495 (4)0.0043 (2)0.053 (1)
C9B0.8469 (4)0.5393 (5)−0.0453 (2)0.063 (1)
C10B0.8675 (5)0.6483 (5)−0.0843 (2)0.067 (1)
C11B0.7974 (5)0.7706 (5)−0.0742 (2)0.067 (1)
C12B0.7071 (4)0.7819 (4)−0.0245 (2)0.055 (1)
C13B0.5938 (4)0.8087 (3)0.1147 (2)0.042 (1)
C14B0.4854 (5)0.8997 (4)0.1371 (2)0.0600 (9)
C15B0.5225 (6)0.9842 (4)0.1693 (2)0.074 (1)
C16B0.6655 (6)0.9776 (4)0.1793 (2)0.068 (1)
C17B0.7743 (5)0.8873 (4)0.1580 (2)0.0630 (9)
C18B0.7399 (4)0.8021 (4)0.1257 (2)0.0518 (9)
C19B0.5724 (4)0.5390 (4)0.1276 (2)0.044 (1)
C20B0.7021 (4)0.4815 (4)0.1613 (2)0.0542 (9)
C21B0.7158 (5)0.3646 (4)0.2027 (2)0.066 (1)
C22B0.6017 (6)0.3070 (4)0.2106 (2)0.069 (1)
C23B0.4745 (5)0.3617 (4)0.1773 (2)0.069 (1)
C24B0.4590 (4)0.4785 (4)0.1354 (2)0.0557 (9)
O1C0.1627 (3)0.7471 (3)0.2192 (1)0.0695 (9)
O2C0.0122 (4)0.7022 (3)0.2938 (2)0.082 (1)
O3C0.0257 (4)0.5591 (3)0.1787 (2)0.081 (1)
O4C0.1584 (4)0.4521 (3)0.2619 (1)0.0750 (9)
C1C0.0866 (4)0.6785 (4)0.2494 (2)0.046 (1)
C2C0.0862 (4)0.5568 (4)0.2260 (2)0.043 (1)
O1D0.1842 (4)0.2373 (3)0.2314 (2)0.085 (1)
O2D0.0341 (4)0.1848 (3)0.3038 (2)0.090 (1)
O3D0.0171 (5)0.0683 (3)0.1861 (2)0.108 (1)
O4D0.1799 (4)−0.0537 (3)0.2558 (1)0.0752 (9)
C1D0.1072 (5)0.1684 (4)0.2579 (2)0.052 (1)
C2D0.0989 (5)0.0538 (4)0.2292 (2)0.053 (1)
HC2A0.40680.29280.53360.059
HC3A0.15660.32910.55940.096
HC4A−0.01900.33890.48340.107
HC5A0.04960.31780.38050.086
HC6A0.29830.28810.35340.054
HC8A0.73500.03690.50020.067
HC9A0.86440.00450.59610.097
HC10A0.88080.18720.63740.090
HC11A0.76520.40110.58570.081
HC12A0.63080.43450.49170.060
HC14A0.42850.05990.40200.074
HC15A0.5134−0.12620.35570.102
HC16A0.7525−0.17320.31630.084
HC17A0.9025−0.03090.31850.077
HC18A0.81780.15880.36060.061
HC20A0.80720.36650.39130.065
HC21A0.85020.55160.32200.088
HC22A0.65560.70040.26010.075
HC23A0.41970.66410.26470.078
HC24A0.37490.47790.33340.062
HC2B0.26790.75050.12400.066
HC3B0.03150.83810.07690.102
HC4B−0.00050.8755−0.03160.105
HC5B0.20340.8322−0.09610.090
HC6B0.44310.7530−0.05120.061
HC8B0.73950.46950.03220.060
HC9B0.89910.4514−0.05280.076
HC10B0.93350.6393−0.12020.080
HC11B0.81210.8501−0.10270.085
HC12B0.65770.8700−0.01650.063
HC14B0.38080.90410.12990.077
HC15B0.44461.05020.18530.104
HC16B0.69151.03940.20240.083
HC17B0.87840.88340.16590.082
HC18B0.81870.73610.11020.065
HC20B0.78450.52390.15560.064
HC21B0.80880.32200.22700.085
HC22B0.61220.22360.24130.083
HC23B0.39320.31800.18310.089
HC24B0.36630.51910.11070.066
H1O4C0.16870.36630.24980.075
H1O4D0.1730−0.13350.24120.075
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P1A0.0307 (6)0.0476 (7)0.0392 (6)−0.0103 (5)0.0018 (5)−0.0038 (5)
C1A0.033 (1)0.054 (2)0.041 (1)−0.010 (1)0.0017 (9)−0.005 (1)
C2A0.038 (1)0.081 (2)0.043 (1)−0.010 (1)0.0065 (9)−0.009 (2)
C3A0.041 (1)0.127 (3)0.056 (1)−0.014 (2)0.013 (1)−0.016 (2)
C4A0.036 (1)0.140 (4)0.071 (2)−0.020 (1)0.011 (1)−0.020 (2)
C5A0.034 (1)0.113 (3)0.068 (2)−0.019 (1)0.001 (1)−0.019 (2)
C6A0.034 (1)0.072 (2)0.051 (1)−0.013 (1)−0.001 (1)−0.011 (2)
C7A0.035 (2)0.055 (2)0.038 (1)−0.010 (1)0.005 (1)−0.006 (1)
C8A0.052 (2)0.060 (2)0.053 (1)−0.013 (1)−0.010 (1)0.004 (1)
C9A0.068 (2)0.086 (2)0.057 (2)−0.020 (2)−0.019 (1)0.010 (2)
C10A0.059 (2)0.109 (3)0.047 (1)−0.021 (2)−0.008 (1)−0.010 (2)
C11A0.047 (2)0.097 (2)0.054 (2)−0.013 (2)0.000 (1)−0.030 (2)
C12A0.039 (1)0.068 (1)0.050 (1)−0.009 (1)0.003 (1)−0.021 (1)
C13A0.043 (2)0.045 (1)0.039 (2)−0.012 (1)0.004 (1)−0.001 (1)
C14A0.063 (2)0.057 (1)0.067 (2)−0.027 (1)0.013 (1)−0.017 (1)
C15A0.091 (2)0.061 (2)0.083 (2)−0.031 (2)0.016 (2)−0.026 (1)
C16A0.088 (2)0.054 (1)0.062 (2)−0.009 (1)0.006 (2)−0.015 (2)
C17A0.062 (2)0.061 (2)0.054 (2)−0.001 (1)0.006 (2)−0.013 (2)
C18A0.045 (1)0.056 (1)0.047 (2)−0.008 (1)0.007 (1)−0.007 (1)
C19A0.036 (1)0.043 (1)0.039 (1)−0.009 (1)0.005 (1)−0.010 (1)
C20A0.045 (1)0.062 (1)0.053 (2)−0.023 (1)0.005 (1)−0.005 (1)
C21A0.069 (2)0.073 (2)0.059 (2)−0.039 (2)0.007 (1)−0.003 (1)
C22A0.087 (2)0.056 (1)0.047 (2)−0.031 (2)0.007 (2)−0.006 (1)
C23A0.073 (2)0.049 (1)0.051 (2)−0.013 (1)−0.001 (2)−0.001 (1)
C24A0.047 (1)0.047 (1)0.048 (1)−0.006 (1)−0.001 (1)−0.003 (1)
P1B0.0391 (6)0.0445 (7)0.0407 (6)−0.0095 (5)−0.0008 (5)−0.0084 (5)
C1B0.042 (1)0.043 (2)0.050 (2)−0.013 (1)−0.001 (1)−0.002 (1)
C2B0.040 (1)0.062 (2)0.074 (1)−0.012 (1)0.007 (1)−0.010 (2)
C3B0.041 (1)0.075 (2)0.116 (3)−0.010 (1)−0.003 (1)−0.010 (2)
C4B0.055 (1)0.067 (2)0.120 (3)−0.016 (1)−0.030 (1)0.006 (2)
C5B0.072 (2)0.063 (2)0.080 (2)−0.027 (2)−0.033 (2)0.012 (2)
C6B0.061 (1)0.054 (2)0.051 (2)−0.022 (1)−0.013 (1)0.004 (1)
C7B0.040 (2)0.053 (2)0.045 (1)−0.012 (1)−0.002 (1)−0.015 (1)
C8B0.045 (1)0.061 (1)0.056 (1)−0.009 (1)0.001 (1)−0.025 (1)
C9B0.046 (2)0.088 (2)0.059 (2)−0.009 (2)0.002 (1)−0.035 (2)
C10B0.046 (2)0.108 (3)0.050 (2)−0.018 (2)0.004 (1)−0.027 (2)
C11B0.056 (2)0.093 (2)0.053 (1)−0.023 (2)0.008 (1)−0.010 (2)
C12B0.051 (1)0.064 (1)0.051 (1)−0.018 (1)0.004 (1)−0.009 (1)
C13B0.050 (2)0.039 (2)0.035 (2)−0.011 (1)0.002 (1)−0.004 (1)
C14B0.064 (1)0.054 (2)0.064 (2)−0.008 (1)0.004 (1)−0.027 (1)
C15B0.092 (2)0.061 (2)0.076 (2)−0.013 (2)−0.001 (2)−0.035 (2)
C16B0.101 (2)0.053 (2)0.055 (2)−0.026 (2)−0.012 (2)−0.013 (2)
C17B0.078 (1)0.058 (2)0.058 (2)−0.029 (2)−0.012 (2)−0.008 (1)
C18B0.055 (1)0.052 (2)0.051 (2)−0.019 (1)−0.003 (1)−0.009 (1)
C19B0.045 (2)0.042 (1)0.043 (2)−0.006 (1)−0.004 (1)−0.012 (1)
C20B0.057 (2)0.047 (1)0.052 (2)−0.001 (1)−0.015 (1)−0.008 (1)
C21B0.089 (2)0.047 (1)0.053 (2)0.000 (1)−0.017 (2)−0.007 (1)
C22B0.111 (3)0.045 (1)0.048 (2)−0.014 (1)−0.002 (2)−0.009 (1)
C23B0.095 (2)0.055 (1)0.060 (2)−0.029 (2)0.005 (2)−0.009 (1)
C24B0.061 (2)0.052 (1)0.057 (2)−0.020 (1)0.000 (1)−0.010 (1)
O1C0.092 (2)0.049 (2)0.078 (2)−0.033 (2)0.033 (2)−0.023 (2)
O2C0.097 (3)0.088 (3)0.088 (3)−0.046 (2)0.042 (2)−0.056 (2)
O3C0.097 (3)0.065 (2)0.079 (2)−0.002 (2)−0.040 (2)−0.028 (2)
O4C0.122 (3)0.036 (2)0.066 (2)−0.020 (2)−0.030 (2)−0.004 (2)
C1C0.044 (3)0.044 (3)0.050 (3)−0.006 (2)−0.002 (2)−0.017 (2)
C2C0.043 (2)0.046 (3)0.044 (3)−0.014 (2)−0.001 (2)−0.014 (2)
O1D0.129 (3)0.059 (2)0.087 (3)−0.057 (2)0.039 (2)−0.024 (2)
O2D0.106 (3)0.093 (3)0.096 (3)−0.051 (2)0.037 (2)−0.049 (2)
O3D0.154 (4)0.076 (3)0.100 (3)−0.042 (2)−0.059 (3)−0.005 (2)
O4D0.098 (2)0.041 (2)0.084 (2)−0.010 (2)−0.012 (2)−0.015 (2)
C1D0.065 (3)0.043 (3)0.049 (3)−0.019 (2)−0.001 (2)−0.005 (2)
C2D0.064 (3)0.046 (3)0.049 (3)−0.023 (2)0.000 (2)0.000 (2)
Geometric parameters (Å, º) top
P1A—C1A1.792 (4)C2B—C3B1.382 (6)
P1A—C7A1.795 (4)C2B—HC2B1.000
P1A—C13A1.786 (4)C3B—C4B1.369 (7)
P1A—C19A1.796 (4)C3B—HC3B1.000
C1A—C2A1.391 (5)C4B—C5B1.380 (7)
C1A—C6A1.397 (5)C4B—HC4B1.000
C2A—C3A1.379 (5)C5B—C6B1.382 (5)
C2A—HC2A1.000C5B—HC5B1.000
C3A—C4A1.375 (6)C6B—HC6B1.000
C3A—HC3A1.000C7B—C8B1.384 (5)
C4A—C5A1.385 (6)C7B—C12B1.397 (5)
C4A—HC4A1.000C8B—C9B1.387 (5)
C5A—C6A1.376 (5)C8B—HC8B1.000
C5A—HC5A1.000C9B—C10B1.371 (6)
C6A—HC6A1.000C9B—HC9B1.000
C7A—C8A1.383 (5)C10B—C11B1.383 (6)
C7A—C12A1.396 (5)C10B—HC10B1.000
C8A—C9A1.389 (5)C11B—C12B1.378 (5)
C8A—HC8A1.000C11B—HC11B1.000
C9A—C10A1.387 (6)C12B—HC12B1.000
C9A—HC9A1.000C13B—C14B1.388 (5)
C10A—C11A1.372 (6)C13B—C18B1.399 (5)
C10A—HC10A1.000C14B—C15B1.383 (5)
C11A—C12A1.380 (5)C14B—HC14B1.000
C11A—HC11A1.000C15B—C16B1.366 (6)
C12A—HC12A1.000C15B—HC15B1.000
C13A—C14A1.386 (5)C16B—C17B1.374 (6)
C13A—C18A1.399 (5)C16B—HC16B1.000
C14A—C15A1.390 (5)C17B—C18B1.379 (5)
C14A—HC14A1.000C17B—HC17B1.000
C15A—C16A1.379 (6)C18B—HC18B1.000
C15A—HC15A1.000C19B—C20B1.391 (5)
C16A—C17A1.372 (6)C19B—C24B1.391 (5)
C16A—HC16A1.000C20B—C21B1.386 (5)
C17A—C18A1.376 (5)C20B—HC20B1.000
C17A—HC17A1.000C21B—C22B1.377 (6)
C18A—HC18A1.000C21B—HC21B1.000
C19A—C20A1.387 (5)C22B—C23B1.365 (6)
C19A—C24A1.394 (5)C22B—HC22B1.000
C20A—C21A1.387 (5)C23B—C24B1.389 (5)
C20A—HC20A1.000C23B—HC23B1.000
C21A—C22A1.375 (6)C24B—HC24B1.000
C21A—HC21A1.000O1C—C1C1.254 (4)
C22A—C23A1.380 (6)O2C—C1C1.222 (4)
C22A—HC22A1.000O3C—C2C1.198 (4)
C23A—C24A1.393 (5)O4C—C2C1.290 (4)
C23A—HC23A1.000O4C—H1O4C1.000
C24A—HC24A1.000C1C—C2C1.513 (5)
P1B—C1B1.796 (4)O1D—C1D1.233 (5)
P1B—C7B1.784 (4)O2D—C1D1.226 (5)
P1B—C13B1.800 (4)O3D—C2D1.205 (5)
P1B—C19B1.795 (4)O4D—C2D1.262 (5)
C1B—C2B1.392 (5)O4D—H1O4D1.000
C1B—C6B1.401 (5)C1D—C2D1.524 (6)
C1A—P1A—C7A108.9 (2)P1B—C1B—C6B120.0 (3)
C1A—P1A—C13A109.4 (2)C2B—C1B—C6B120.4 (4)
C1A—P1A—C19A110.8 (2)C1B—C2B—C3B118.7 (4)
C7A—P1A—C13A108.7 (2)C1B—C2B—HC2B120.6
C7A—P1A—C19A107.9 (2)C3B—C2B—HC2B120.6
C13A—P1A—C19A111.1 (2)C2B—C3B—C4B121.0 (5)
P1A—C1A—C2A120.8 (3)C2B—C3B—HC3B119.5
P1A—C1A—C6A119.5 (3)C4B—C3B—HC3B119.5
C2A—C1A—C6A119.7 (3)C3B—C4B—C5B120.4 (4)
C1A—C2A—C3A120.0 (4)C3B—C4B—HC4B119.8
C1A—C2A—HC2A120.0C5B—C4B—HC4B119.8
C3A—C2A—HC2A120.0C4B—C5B—C6B120.0 (4)
C2A—C3A—C4A119.5 (4)C4B—C5B—HC5B120.0
C2A—C3A—HC3A120.2C6B—C5B—HC5B120.0
C4A—C3A—HC3A120.2C1B—C6B—C5B119.2 (4)
C3A—C4A—C5A121.5 (4)C1B—C6B—HC6B120.4
C3A—C4A—HC4A119.3C5B—C6B—HC6B120.4
C5A—C4A—HC4A119.3P1B—C7B—C8B121.6 (3)
C4A—C5A—C6A119.1 (4)P1B—C7B—C12B118.9 (3)
C4A—C5A—HC5A120.4C8B—C7B—C12B119.5 (4)
C6A—C5A—HC5A120.4C7B—C8B—C9B119.4 (4)
C1A—C6A—C5A120.2 (4)C7B—C8B—HC8B120.3
C1A—C6A—HC6A119.9C9B—C8B—HC8B120.3
C5A—C6A—HC6A119.9C8B—C9B—C10B120.8 (4)
P1A—C7A—C8A120.6 (3)C8B—C9B—HC9B119.6
P1A—C7A—C12A119.1 (3)C10B—C9B—HC9B119.6
C8A—C7A—C12A120.3 (4)C9B—C10B—C11B120.3 (4)
C7A—C8A—C9A119.3 (4)C9B—C10B—HC10B119.8
C7A—C8A—HC8A120.3C11B—C10B—HC10B119.8
C9A—C8A—HC8A120.3C10B—C11B—C12B119.4 (4)
C8A—C9A—C10A119.9 (4)C10B—C11B—HC11B120.3
C8A—C9A—HC9A120.1C12B—C11B—HC11B120.3
C10A—C9A—HC9A120.1C7B—C12B—C11B120.6 (4)
C9A—C10A—C11A120.8 (4)C7B—C12B—HC12B119.7
C9A—C10A—HC10A119.6C11B—C12B—HC12B119.7
C11A—C10A—HC10A119.6P1B—C13B—C14B122.6 (3)
C10A—C11A—C12A119.7 (4)P1B—C13B—C18B117.7 (3)
C10A—C11A—HC11A120.1C14B—C13B—C18B119.7 (4)
C12A—C11A—HC11A120.1C13B—C14B—C15B119.8 (4)
C7A—C12A—C11A120.0 (4)C13B—C14B—HC14B120.1
C7A—C12A—HC12A120.0C15B—C14B—HC14B120.1
C11A—C12A—HC12A120.0C14B—C15B—C16B120.0 (4)
P1A—C13A—C14A122.6 (3)C14B—C15B—HC15B120.0
P1A—C13A—C18A118.0 (3)C16B—C15B—HC15B120.0
C14A—C13A—C18A119.4 (4)C15B—C16B—C17B121.0 (4)
C13A—C14A—C15A120.0 (4)C15B—C16B—HC16B119.5
C13A—C14A—HC14A120.0C17B—C16B—HC16B119.5
C15A—C14A—HC14A120.0C16B—C17B—C18B120.0 (4)
C14A—C15A—C16A119.9 (4)C16B—C17B—HC17B120.0
C14A—C15A—HC15A120.0C18B—C17B—HC17B120.0
C16A—C15A—HC15A120.0C13B—C18B—C17B119.5 (4)
C15A—C16A—C17A120.2 (4)C13B—C18B—HC18B120.2
C15A—C16A—HC16A119.9C17B—C18B—HC18B120.2
C17A—C16A—HC16A119.9P1B—C19B—C20B118.9 (3)
C16A—C17A—C18A120.7 (4)P1B—C19B—C24B121.2 (3)
C16A—C17A—HC17A119.6C20B—C19B—C24B119.9 (4)
C18A—C17A—HC17A119.6C19B—C20B—C21B119.2 (4)
C13A—C18A—C17A119.8 (4)C19B—C20B—HC20B120.4
C13A—C18A—HC18A120.1C21B—C20B—HC20B120.4
C17A—C18A—HC18A120.1C20B—C21B—C22B120.1 (4)
P1A—C19A—C20A119.1 (3)C20B—C21B—HC21B119.9
P1A—C19A—C24A121.1 (3)C22B—C21B—HC21B119.9
C20A—C19A—C24A119.7 (4)C21B—C22B—C23B121.2 (4)
C19A—C20A—C21A120.5 (4)C21B—C22B—HC22B119.4
C19A—C20A—HC20A119.8C23B—C22B—HC22B119.4
C21A—C20A—HC20A119.8C22B—C23B—C24B119.5 (4)
C20A—C21A—C22A119.6 (4)C22B—C23B—HC23B120.3
C20A—C21A—HC21A120.2C24B—C23B—HC23B120.3
C22A—C21A—HC21A120.2C19B—C24B—C23B120.0 (4)
C21A—C22A—C23A120.7 (4)C19B—C24B—HC24B120.0
C21A—C22A—HC22A119.7C23B—C24B—HC24B120.0
C23A—C22A—HC22A119.7C2C—O4C—H1O4C119.3
C22A—C23A—C24A120.2 (4)O1C—C1C—O2C126.6 (4)
C22A—C23A—HC23A119.9O1C—C1C—C2C115.1 (4)
C24A—C23A—HC23A119.9O2C—C1C—C2C118.3 (4)
C19A—C24A—C23A119.3 (4)O3C—C2C—O4C124.3 (4)
C19A—C24A—HC24A120.3O3C—C2C—C1C122.8 (4)
C23A—C24A—HC24A120.3O4C—C2C—C1C112.9 (3)
C1B—P1B—C7B108.7 (2)C2D—O4D—H1O4D117.7
C1B—P1B—C13B110.6 (2)O1D—C1D—O2D126.8 (4)
C1B—P1B—C19B110.3 (2)O1D—C1D—C2D116.2 (4)
C7B—P1B—C13B107.4 (2)O2D—C1D—C2D117.0 (4)
C7B—P1B—C19B109.8 (2)O3D—C2D—O4D124.9 (4)
C13B—P1B—C19B110.0 (2)O3D—C2D—C1D120.9 (4)
P1B—C1B—C2B119.5 (3)O4D—C2D—C1D114.1 (4)
C7A—P1A—C1A—C2A8.2 (4)C1B—P1B—C7B—C8B−105.3 (3)
C7A—P1A—C1A—C6A−172.6 (3)C1B—P1B—C7B—C12B71.0 (3)
C13A—P1A—C1A—C2A126.8 (3)C13B—P1B—C7B—C8B135.0 (3)
C13A—P1A—C1A—C6A−54.0 (4)C13B—P1B—C7B—C12B−48.7 (3)
C19A—P1A—C1A—C2A−110.3 (3)C19B—P1B—C7B—C8B15.4 (4)
C19A—P1A—C1A—C6A68.9 (4)C19B—P1B—C7B—C12B−168.3 (3)
C1A—P1A—C7A—C8A97.2 (3)C1B—P1B—C13B—C14B24.5 (4)
C1A—P1A—C7A—C12A−80.2 (3)C1B—P1B—C13B—C18B−158.6 (3)
C13A—P1A—C7A—C8A−21.9 (4)C7B—P1B—C13B—C14B143.0 (3)
C13A—P1A—C7A—C12A160.7 (3)C7B—P1B—C13B—C18B−40.1 (3)
C19A—P1A—C7A—C8A−142.4 (3)C19B—P1B—C13B—C14B−97.6 (3)
C19A—P1A—C7A—C12A40.2 (3)C19B—P1B—C13B—C18B79.3 (3)
C1A—P1A—C13A—C14A−7.9 (4)C1B—P1B—C19B—C20B−177.1 (3)
C1A—P1A—C13A—C18A174.2 (3)C1B—P1B—C19B—C24B2.8 (4)
C7A—P1A—C13A—C14A110.9 (3)C7B—P1B—C19B—C20B63.1 (3)
C7A—P1A—C13A—C18A−67.0 (3)C7B—P1B—C19B—C24B−117.0 (3)
C19A—P1A—C13A—C14A−130.6 (3)C13B—P1B—C19B—C20B−54.8 (3)
C19A—P1A—C13A—C18A51.5 (3)C13B—P1B—C19B—C24B125.1 (3)
C1A—P1A—C19A—C20A156.9 (3)P1B—C1B—C2B—C3B177.8 (3)
C1A—P1A—C19A—C24A−25.5 (4)P1B—C1B—C2B—HC2B−2.2
C7A—P1A—C19A—C20A37.8 (4)C6B—C1B—C2B—C3B−3.2 (6)
C7A—P1A—C19A—C24A−144.6 (3)C6B—C1B—C2B—HC2B176.8
C13A—P1A—C19A—C20A−81.2 (3)P1B—C1B—C6B—C5B−179.2 (3)
C13A—P1A—C19A—C24A96.4 (3)P1B—C1B—C6B—HC6B0.8
P1A—C1A—C2A—C3A178.7 (4)C2B—C1B—C6B—C5B1.8 (6)
P1A—C1A—C2A—HC2A−1.3C2B—C1B—C6B—HC6B−178.2
C6A—C1A—C2A—C3A−0.5 (6)C1B—C2B—C3B—C4B2.6 (7)
C6A—C1A—C2A—HC2A179.5C1B—C2B—C3B—HC3B−177.4
P1A—C1A—C6A—C5A−179.7 (3)HC2B—C2B—C3B—C4B−177.4
P1A—C1A—C6A—HC6A0.3HC2B—C2B—C3B—HC3B2.6
C2A—C1A—C6A—C5A−0.5 (6)C2B—C3B—C4B—C5B−0.7 (8)
C2A—C1A—C6A—HC6A179.5C2B—C3B—C4B—HC4B179.3
C1A—C2A—C3A—C4A1.2 (7)HC3B—C3B—C4B—C5B179.3
C1A—C2A—C3A—HC3A−178.8HC3B—C3B—C4B—HC4B−0.7
HC2A—C2A—C3A—C4A−178.8C3B—C4B—C5B—C6B−0.7 (7)
HC2A—C2A—C3A—HC3A1.2C3B—C4B—C5B—HC5B179.3
C2A—C3A—C4A—C5A−0.8 (8)HC4B—C4B—C5B—C6B179.3
C2A—C3A—C4A—HC4A179.2HC4B—C4B—C5B—HC5B−0.7
HC3A—C3A—C4A—C5A179.2C4B—C5B—C6B—C1B0.2 (6)
HC3A—C3A—C4A—HC4A−0.8C4B—C5B—C6B—HC6B−179.8
C3A—C4A—C5A—C6A−0.3 (8)HC5B—C5B—C6B—C1B−179.8
C3A—C4A—C5A—HC5A179.7HC5B—C5B—C6B—HC6B0.2
HC4A—C4A—C5A—C6A179.7P1B—C7B—C8B—C9B175.9 (3)
HC4A—C4A—C5A—HC5A−0.3P1B—C7B—C8B—HC8B−4.1
C4A—C5A—C6A—C1A0.9 (7)C12B—C7B—C8B—C9B−0.4 (6)
C4A—C5A—C6A—HC6A−179.1C12B—C7B—C8B—HC8B179.6
HC5A—C5A—C6A—C1A−179.1P1B—C7B—C12B—C11B−175.0 (3)
HC5A—C5A—C6A—HC6A0.9P1B—C7B—C12B—HC12B5.0
P1A—C7A—C8A—C9A−175.7 (3)C8B—C7B—C12B—C11B1.3 (6)
P1A—C7A—C8A—HC8A4.3C8B—C7B—C12B—HC12B−178.7
C12A—C7A—C8A—C9A1.7 (6)C7B—C8B—C9B—C10B−0.6 (6)
C12A—C7A—C8A—HC8A−178.3C7B—C8B—C9B—HC9B179.4
P1A—C7A—C12A—C11A176.6 (3)HC8B—C8B—C9B—C10B179.4
P1A—C7A—C12A—HC12A−3.4HC8B—C8B—C9B—HC9B−0.6
C8A—C7A—C12A—C11A−0.8 (6)C8B—C9B—C10B—C11B0.7 (6)
C8A—C7A—C12A—HC12A179.2C8B—C9B—C10B—HC10B−179.3
C7A—C8A—C9A—C10A−1.6 (7)HC9B—C9B—C10B—C11B−179.3
C7A—C8A—C9A—HC9A178.4HC9B—C9B—C10B—HC10B0.7
HC8A—C8A—C9A—C10A178.4C9B—C10B—C11B—C12B0.2 (6)
HC8A—C8A—C9A—HC9A−1.6C9B—C10B—C11B—HC11B−179.8
C8A—C9A—C10A—C11A0.7 (7)HC10B—C10B—C11B—C12B−179.8
C8A—C9A—C10A—HC10A−179.3HC10B—C10B—C11B—HC11B0.2
HC9A—C9A—C10A—C11A−179.3C10B—C11B—C12B—C7B−1.2 (6)
HC9A—C9A—C10A—HC10A0.7C10B—C11B—C12B—HC12B178.8
C9A—C10A—C11A—C12A0.2 (7)HC11B—C11B—C12B—C7B178.8
C9A—C10A—C11A—HC11A−179.8HC11B—C11B—C12B—HC12B−1.2
HC10A—C10A—C11A—C12A−179.8P1B—C13B—C14B—C15B177.7 (3)
HC10A—C10A—C11A—HC11A0.2P1B—C13B—C14B—HC14B−2.3
C10A—C11A—C12A—C7A−0.2 (6)C18B—C13B—C14B—C15B0.9 (6)
C10A—C11A—C12A—HC12A179.8C18B—C13B—C14B—HC14B−179.1
HC11A—C11A—C12A—C7A179.8P1B—C13B—C18B—C17B−177.8 (3)
HC11A—C11A—C12A—HC12A−0.2P1B—C13B—C18B—HC18B2.2
P1A—C13A—C14A—C15A−178.4 (3)C14B—C13B—C18B—C17B−0.8 (6)
P1A—C13A—C14A—HC14A1.6C14B—C13B—C18B—HC18B179.2
C18A—C13A—C14A—C15A−0.5 (6)C13B—C14B—C15B—C16B−0.3 (7)
C18A—C13A—C14A—HC14A179.5C13B—C14B—C15B—HC15B179.7
P1A—C13A—C18A—C17A177.2 (3)HC14B—C14B—C15B—C16B179.7
P1A—C13A—C18A—HC18A−2.8HC14B—C14B—C15B—HC15B−0.3
C14A—C13A—C18A—C17A−0.8 (6)C14B—C15B—C16B—C17B−0.3 (7)
C14A—C13A—C18A—HC18A179.2C14B—C15B—C16B—HC16B179.7
C13A—C14A—C15A—C16A1.7 (7)HC15B—C15B—C16B—C17B179.7
C13A—C14A—C15A—HC15A−178.3HC15B—C15B—C16B—HC16B−0.3
HC14A—C14A—C15A—C16A−178.3C15B—C16B—C17B—C18B0.4 (7)
HC14A—C14A—C15A—HC15A1.7C15B—C16B—C17B—HC17B−179.6
C14A—C15A—C16A—C17A−1.5 (7)HC16B—C16B—C17B—C18B−179.6
C14A—C15A—C16A—HC16A178.5HC16B—C16B—C17B—HC17B0.4
HC15A—C15A—C16A—C17A178.5C16B—C17B—C18B—C13B0.2 (6)
HC15A—C15A—C16A—HC16A−1.5C16B—C17B—C18B—HC18B−179.8
C15A—C16A—C17A—C18A0.3 (7)HC17B—C17B—C18B—C13B−179.8
C15A—C16A—C17A—HC17A−179.7HC17B—C17B—C18B—HC18B0.2
HC16A—C16A—C17A—C18A−179.7P1B—C19B—C20B—C21B179.2 (3)
HC16A—C16A—C17A—HC17A0.3P1B—C19B—C20B—HC20B−0.8
C16A—C17A—C18A—C13A0.9 (6)C24B—C19B—C20B—C21B−0.7 (6)
C16A—C17A—C18A—HC18A−179.1C24B—C19B—C20B—HC20B179.3
HC17A—C17A—C18A—C13A−179.1P1B—C19B—C24B—C23B−178.9 (3)
HC17A—C17A—C18A—HC18A0.9P1B—C19B—C24B—HC24B1.1
P1A—C19A—C20A—C21A178.5 (3)C20B—C19B—C24B—C23B0.9 (6)
P1A—C19A—C20A—HC20A−1.5C20B—C19B—C24B—HC24B−179.1
C24A—C19A—C20A—C21A0.9 (6)C19B—C20B—C21B—C22B−0.4 (6)
C24A—C19A—C20A—HC20A−179.1C19B—C20B—C21B—HC21B179.6
P1A—C19A—C24A—C23A−178.7 (3)HC20B—C20B—C21B—C22B179.6
P1A—C19A—C24A—HC24A1.3HC20B—C20B—C21B—HC21B−0.4
C20A—C19A—C24A—C23A−1.2 (6)C20B—C21B—C22B—C23B1.2 (7)
C20A—C19A—C24A—HC24A178.8C20B—C21B—C22B—HC22B−178.8
C19A—C20A—C21A—C22A0.1 (7)HC21B—C21B—C22B—C23B−178.8
C19A—C20A—C21A—HC21A−179.9HC21B—C21B—C22B—HC22B1.2
HC20A—C20A—C21A—C22A−179.9C21B—C22B—C23B—C24B−1.0 (7)
HC20A—C20A—C21A—HC21A0.1C21B—C22B—C23B—HC23B179.0
C20A—C21A—C22A—C23A−0.8 (7)HC22B—C22B—C23B—C24B179.0
C20A—C21A—C22A—HC22A179.2HC22B—C22B—C23B—HC23B−1.0
HC21A—C21A—C22A—C23A179.2C22B—C23B—C24B—C19B−0.1 (7)
HC21A—C21A—C22A—HC22A−0.8C22B—C23B—C24B—HC24B179.9
C21A—C22A—C23A—C24A0.5 (7)HC23B—C23B—C24B—C19B179.9
C21A—C22A—C23A—HC23A−179.5HC23B—C23B—C24B—HC24B−0.1
HC22A—C22A—C23A—C24A−179.5H1O4C—O4C—C2C—O3C2.2
HC22A—C22A—C23A—HC23A0.5H1O4C—O4C—C2C—C1C−177.3
C22A—C23A—C24A—C19A0.4 (6)O1C—C1C—C2C—O3C−71.5 (5)
C22A—C23A—C24A—HC24A−179.6O1C—C1C—C2C—O4C108.0 (4)
HC23A—C23A—C24A—C19A−179.6O2C—C1C—C2C—O3C106.9 (5)
HC23A—C23A—C24A—HC24A0.4O2C—C1C—C2C—O4C−73.6 (5)
C7B—P1B—C1B—C2B178.9 (3)H1O4D—O4D—C2D—O3D−2.6
C7B—P1B—C1B—C6B−0.1 (4)H1O4D—O4D—C2D—C1D175.1
C13B—P1B—C1B—C2B−63.4 (4)O1D—C1D—C2D—O3D−82.3 (6)
C13B—P1B—C1B—C6B117.6 (3)O1D—C1D—C2D—O4D99.8 (5)
C19B—P1B—C1B—C2B58.5 (4)O2D—C1D—C2D—O3D95.8 (5)
C19B—P1B—C1B—C6B−120.5 (3)O2D—C1D—C2D—O4D−82.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4C—H1O4C···O1D1.001.512.505 (2)180
O4D—H1O4D···O1Ci1.001.502.500 (2)180
Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC24H20P+·C2HO4−
Mr428.4
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)9.517 (5), 10.860 (7), 22.032 (9)
α, β, γ (°)78.49 (3), 88.37 (2), 75.13 (3)
V (Å3)2156 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.15
Crystal size (mm)0.25 × 0.20 × 0.05
Data collection
DiffractometerNonius CAD-4
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		8001, 7564, 4017
Rint0.019
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.053, 1.35
No. of reflections4017
No. of parameters367
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.53, −0.91

Computer programs: CAD-4 (Schagen et al., 1989), CAD-4, SIR92 (Altomare et al., 1994), RAELS (Rae, 2000), ORTEPII (Johnson, 1976) and CrystalMaker (CrystalMaker Software, 2005), Local programs.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4C—H1O4C···O1D1.001.512.505 (2)180
O4D—H1O4D···O1Ci1.001.502.500 (2)180
Symmetry code: (i) x, y−1, z.
 

Acknowledgements

This research was supported by the Australian Research Council and the University of New South Wales. PAWD is grateful to the University of Western Ontario for sabbatical leave, during which this work was carried out.

References

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 First citationRodrigues, V. H., Paixão, J. A., Costa, M. M. R. R. & Matos Beja, A. (2001). Acta Cryst. C57, 213–215.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSchagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Manual. Version 5.0. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationScudder, M. L. & Dance, I. G. (1998). J. Chem. Soc. Dalton Trans. pp. 3167–3175.  Web of Science CrossRef Google Scholar

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o243
https://doi.org/10.1107/S160053680706463X
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