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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2675–o2676.
Published online 2010 September 30. doi:  10.1107/S1600536810038286
PMCID: PMC2983122

Triphen­yl[(4-phenyl­benzo­yl)meth­yl]phospho­nium trifluoro­methane­sulfonate

Abstract

In the cation of the title compound, C32H26OP+·CF3O3S, the dihedral angle between the benzene rings of the biphenyl group is 42.37 (8)°. In the crystal, the cations and anions inter­act through inter­molecular C—H(...)O hydrogen bonds, forming chains parallel to the b axis. These chains are further linked by C—H(...)π stacking inter­actions into layers parallel to the bc plane.

Related literature

For the synthesis and characterization of phospho­rus ylide metal complexes, see: Kalyanasundari et al. (1995 [triangle], 1999 [triangle]); Laavanya et al. (2001 [triangle]); Vicente et al. (1985 [triangle]); Karami (2007 [triangle], 2008 [triangle]); Akkurt et al. (2008 [triangle]). For related structures, see: Karami & Büyükgüngör (2009 [triangle]); Shao et al. (1982 [triangle]). For the synthesis of the title compound, see: Burmeister et al. (1973 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2675-scheme1.jpg

Experimental

Crystal data

  • C32H26OP+·CF3O3S
  • M r = 606.58
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2675-efi1.jpg
  • a = 9.0559 (10) Å
  • b = 19.382 (2) Å
  • c = 16.5396 (19) Å
  • β = 92.577 (2)°
  • V = 2900.1 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 294 K
  • 0.25 × 0.20 × 0.17 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.936, T max = 0.974
  • 29195 measured reflections
  • 5245 independent reflections
  • 3748 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.139
  • S = 1.06
  • 5245 reflections
  • 379 parameters
  • H-atom parameters constrained
  • Δρmax = 0.56 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT-Plus (Bruker, 1998 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and SCHAKAL97 (Keller, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038286/lx2176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038286/lx2176Isup2.hkl

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

Acknowledgments

Financial support from the Universitá degli Studi di Parma is gratefully acknowledged.

supplementary crystallographic information

Comment

The synthesis of α–ketostabilized phosphorus ylides has attracted much interest over the last decades due to their stability and ability to act as bifunctional ligands (C- versus O-coordination; Kalyanasundari et al., 1995; Kalyanasundari et al., 1999; Laavanya et al., 2001; Vicente et al., 1985). In this respect, the preferred coordination modes of 4-flourobenzyloxymethylenetriphenylphosphorane ylide (FBPPY), 4-chlorobenzyl-oxymethylenetriphenylphosphorane ylide (CBPPY), and 4-methoxybenzoylmethylenetriphenylphosphorane ylide (MOBPPY) to transition metals such as mercury (II), silver (I) and palladium (II) have been recently investigated by our group (Karami, 2007, 2008; Akkurt et al., 2008). As a part of our ongoing study on the synthesis and characterization of new trifluoromethanesulfonate phosphonium ylides, the title compound has been prepared according to the sequence shown in Figure 3 (Burmeister et al., 1973), and its crystal structure is reported herein.

In the title compound (Fig. 1), bond lengths and angles within the phosphonium cation are not unusual and comparable to those observed for the related 4-methoxybenzoylmethyl derivative (Karami & Büyükgüngör, 2009). The P1–C1 bond length (1.798 (2) Å) is significantly longer than that reported in the free ylide (1.711 Å) of formula Ph3PC(H)COPh (Shao et al., 1982). The dihedral angle between the benzene rings of the biphenyl group is 42.37 (8)°. Unlike the 4-methoxybenzoylmethyl derivative, the conformation of the cation is not stabilized by intramolecular hydrogen bonds. In the crystal packing (Fig. 2), cations and anions are linked by intermolecular C—H···O hydrogen bonds into chains running parallel to the b axis (see Fig. 2 & Table 1). The chains further interact through C—H···π stacking interactions to form layers parallel to the bc plane (see Fig. 2 & Table 1).

Experimental

The title compound was obtained by reaction of (4–phenylbenzoylmethyl)triphenylphosphonium bromide and AgOTf (OTf : trifluoromethanesulfonate) in dry acetone in a 1:1 molar ratio under stirring for 12 h (Fig. 3). The precipitate obtained was washed several times with dry diethyl ether and dried in a vacuum. Orange crystals of the title compound suitable for X–ray analysis formed by addition of dry diethyl ether to a chloroform solution. The crystals are air stable and resistant against moisture.

Refinement

All H atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms are presented as a small spheres of arbitrary radius.
Fig. 2.
A view of the C—H···O and C—H···π interactions (dashed lines) in the crystal structure of the title compound.
Fig. 3.
The procedure adopted for the synthesis of the title compound.

Crystal data

C32H26OP+·CF3O3SF(000) = 1256
Mr = 606.58Dx = 1.389 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 744 reflections
a = 9.0559 (10) Åθ = 6.3–22.4°
b = 19.382 (2) ŵ = 0.22 mm1
c = 16.5396 (19) ÅT = 294 K
β = 92.577 (2)°Block, orange
V = 2900.1 (6) Å30.25 × 0.20 × 0.17 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer5245 independent reflections
Radiation source: fine-focus sealed tube3748 reflections with I > 2σ(I)
graphiteRint = 0.043
ω scansθmax = 25.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −10→10
Tmin = 0.936, Tmax = 0.974k = −23→23
29195 measured reflectionsl = −19→19

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)] = 0.048Hydrogen site location: difference Fourier map
wR(F2) = 0.139H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.082P)2] where P = (Fo2 + 2Fc2)/3
5245 reflections(Δ/σ)max < 0.001
379 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = −0.29 e Å3

Special details

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)

xyzUiso*/Ueq
P10.05841 (6)0.19921 (3)0.17248 (4)0.03733 (18)
S10.78232 (9)0.42703 (4)0.27665 (5)0.0666 (2)
F10.5564 (3)0.35241 (16)0.3102 (3)0.1880 (17)
F20.5301 (3)0.45799 (15)0.3327 (2)0.1577 (13)
F30.6656 (4)0.39779 (16)0.41126 (19)0.1544 (13)
O10.29798 (19)0.28836 (9)0.13868 (13)0.0625 (5)
O20.7193 (4)0.4436 (2)0.19884 (16)0.1420 (13)
O30.8484 (3)0.48364 (11)0.31695 (15)0.0894 (7)
O40.8683 (3)0.36544 (12)0.28273 (18)0.1039 (9)
C10.0380 (3)0.28830 (11)0.14394 (15)0.0435 (6)
H1A−0.02070.29130.09350.052*
H1B−0.01450.31260.18510.052*
C20.1864 (3)0.32291 (12)0.13352 (15)0.0449 (6)
C30.1899 (2)0.39764 (12)0.11621 (14)0.0433 (6)
C40.0651 (3)0.43896 (12)0.11089 (15)0.0459 (6)
H4−0.02670.42020.12110.055*
C50.0757 (3)0.50804 (12)0.09048 (15)0.0453 (6)
H5−0.00880.53540.08830.054*
C60.2109 (3)0.53701 (12)0.07326 (14)0.0433 (6)
C70.3360 (3)0.49527 (13)0.08168 (17)0.0535 (7)
H70.42820.51400.07240.064*
C80.3263 (3)0.42769 (13)0.10323 (17)0.0523 (7)
H80.41190.40130.10930.063*
C90.2251 (3)0.60970 (12)0.04788 (14)0.0437 (6)
C100.1499 (3)0.66280 (13)0.08446 (16)0.0549 (7)
H100.08250.65260.12350.066*
C110.1740 (3)0.73053 (14)0.06349 (18)0.0651 (8)
H110.12350.76570.08880.078*
C120.2723 (3)0.74644 (14)0.00535 (18)0.0613 (7)
H120.29130.7923−0.00700.074*
C130.3418 (3)0.69483 (15)−0.03417 (18)0.0601 (7)
H130.40480.7055−0.07530.072*
C140.3188 (3)0.62676 (13)−0.01322 (17)0.0539 (7)
H140.36670.5919−0.04040.065*
C150.1376 (3)0.14886 (12)0.09454 (14)0.0414 (5)
C160.0457 (3)0.12156 (13)0.03274 (15)0.0530 (6)
H16−0.05550.12990.03200.064*
C170.1047 (4)0.08214 (16)−0.02744 (18)0.0690 (8)
H170.04370.0642−0.06900.083*
C180.2538 (4)0.06968 (16)−0.02533 (19)0.0763 (9)
H180.29330.0427−0.06550.092*
C190.3454 (3)0.09620 (16)0.03476 (19)0.0677 (8)
H190.44630.08720.03530.081*
C200.2880 (3)0.13635 (13)0.09469 (15)0.0511 (6)
H200.35050.15500.13520.061*
C210.1644 (2)0.19295 (12)0.26621 (14)0.0398 (5)
C220.1840 (3)0.24969 (14)0.31672 (16)0.0594 (7)
H220.14940.29290.30030.071*
C230.2550 (4)0.24155 (19)0.39123 (19)0.0771 (9)
H230.26900.27960.42490.093*
C240.3053 (3)0.1785 (2)0.41654 (18)0.0728 (9)
H240.35360.17390.46700.087*
C250.2845 (3)0.12184 (17)0.36745 (17)0.0627 (7)
H250.31770.07880.38510.075*
C260.2145 (3)0.12866 (13)0.29199 (15)0.0476 (6)
H260.20110.09030.25860.057*
C27−0.1209 (2)0.16470 (12)0.19059 (13)0.0389 (5)
C28−0.2382 (3)0.20647 (13)0.20946 (15)0.0473 (6)
H28−0.22850.25420.20780.057*
C29−0.3701 (3)0.17695 (15)0.23093 (18)0.0591 (7)
H29−0.44940.20500.24310.071*
C30−0.3841 (3)0.10673 (15)0.23429 (17)0.0576 (7)
H30−0.47290.08720.24880.069*
C31−0.2677 (3)0.06509 (14)0.21634 (16)0.0555 (7)
H31−0.27810.01740.21880.067*
C32−0.1356 (3)0.09315 (12)0.19477 (15)0.0469 (6)
H32−0.05670.06470.18310.056*
C330.6237 (4)0.4073 (2)0.3325 (3)0.0963 (13)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0344 (3)0.0359 (3)0.0418 (3)−0.0018 (2)0.0030 (2)−0.0002 (3)
S10.0717 (5)0.0581 (5)0.0714 (5)−0.0069 (4)0.0203 (4)−0.0080 (4)
F10.116 (2)0.126 (2)0.327 (5)−0.0639 (19)0.070 (3)−0.014 (3)
F20.0997 (18)0.150 (2)0.229 (3)0.0702 (17)0.0710 (19)0.072 (2)
F30.179 (3)0.161 (3)0.130 (2)0.054 (2)0.077 (2)0.072 (2)
O10.0444 (10)0.0477 (11)0.0966 (15)0.0018 (8)0.0148 (10)0.0106 (10)
O20.148 (3)0.214 (4)0.0626 (17)−0.034 (2)−0.0075 (17)0.0103 (19)
O30.1034 (17)0.0534 (12)0.1110 (19)−0.0142 (12)0.0002 (14)−0.0081 (12)
O40.1033 (18)0.0602 (14)0.153 (3)0.0123 (13)0.0578 (17)−0.0148 (14)
C10.0414 (13)0.0375 (13)0.0520 (14)−0.0040 (10)0.0054 (11)0.0025 (10)
C20.0416 (14)0.0432 (13)0.0507 (14)−0.0023 (11)0.0098 (11)0.0003 (11)
C30.0420 (13)0.0422 (13)0.0462 (14)−0.0041 (10)0.0084 (10)−0.0010 (10)
C40.0384 (13)0.0478 (14)0.0517 (14)−0.0064 (11)0.0058 (11)0.0020 (11)
C50.0424 (13)0.0436 (14)0.0503 (14)0.0012 (11)0.0061 (11)0.0007 (11)
C60.0464 (14)0.0426 (13)0.0414 (13)−0.0025 (11)0.0066 (10)−0.0041 (10)
C70.0417 (14)0.0457 (15)0.0742 (18)−0.0067 (11)0.0147 (13)0.0010 (13)
C80.0387 (13)0.0423 (14)0.0769 (19)0.0013 (11)0.0137 (12)−0.0007 (12)
C90.0452 (13)0.0424 (13)0.0435 (13)−0.0021 (11)0.0018 (11)−0.0002 (10)
C100.0666 (17)0.0495 (16)0.0497 (15)0.0016 (13)0.0129 (13)−0.0033 (12)
C110.091 (2)0.0433 (15)0.0612 (18)0.0113 (15)0.0022 (16)−0.0048 (13)
C120.0691 (18)0.0428 (15)0.0709 (19)−0.0043 (13)−0.0090 (15)0.0096 (13)
C130.0476 (15)0.0601 (18)0.0730 (19)−0.0016 (13)0.0078 (13)0.0194 (15)
C140.0504 (15)0.0471 (15)0.0652 (17)0.0008 (12)0.0148 (13)0.0026 (12)
C150.0467 (14)0.0397 (13)0.0382 (13)0.0008 (10)0.0056 (10)0.0023 (10)
C160.0560 (15)0.0547 (16)0.0481 (15)−0.0007 (12)0.0000 (12)−0.0033 (12)
C170.088 (2)0.068 (2)0.0516 (17)−0.0058 (17)0.0021 (15)−0.0153 (14)
C180.102 (3)0.071 (2)0.0576 (19)0.0077 (19)0.0256 (18)−0.0164 (15)
C190.0650 (18)0.0716 (19)0.068 (2)0.0138 (15)0.0215 (15)−0.0001 (16)
C200.0474 (15)0.0577 (16)0.0488 (15)0.0050 (12)0.0083 (12)−0.0014 (12)
C210.0345 (12)0.0438 (13)0.0413 (13)−0.0028 (10)0.0044 (9)−0.0023 (10)
C220.0720 (19)0.0517 (16)0.0539 (17)−0.0014 (14)−0.0032 (14)−0.0094 (13)
C230.087 (2)0.085 (2)0.0588 (19)−0.0074 (19)−0.0087 (16)−0.0219 (17)
C240.0621 (19)0.107 (3)0.0481 (17)0.0019 (18)−0.0105 (14)−0.0032 (17)
C250.0531 (16)0.078 (2)0.0571 (18)0.0112 (14)−0.0008 (13)0.0138 (15)
C260.0446 (14)0.0495 (15)0.0485 (14)0.0015 (11)0.0005 (11)0.0010 (11)
C270.0351 (12)0.0427 (13)0.0387 (12)−0.0022 (10)−0.0001 (10)0.0016 (10)
C280.0417 (13)0.0434 (14)0.0567 (15)−0.0007 (11)0.0018 (11)−0.0025 (11)
C290.0372 (14)0.0685 (19)0.0719 (19)0.0000 (13)0.0076 (13)−0.0009 (14)
C300.0399 (14)0.0691 (19)0.0642 (18)−0.0146 (13)0.0041 (12)0.0028 (14)
C310.0545 (16)0.0468 (15)0.0649 (18)−0.0150 (12)0.0011 (13)0.0038 (12)
C320.0434 (13)0.0422 (14)0.0554 (15)−0.0022 (11)0.0039 (11)0.0027 (11)
C330.078 (2)0.077 (3)0.137 (4)0.019 (2)0.036 (2)0.028 (2)

Geometric parameters (Å, °)

P1—C211.790 (2)C13—H130.9300
P1—C151.792 (2)C14—H140.9300
P1—C271.794 (2)C15—C201.383 (3)
P1—C11.798 (2)C15—C161.393 (3)
S1—O31.404 (2)C16—C171.381 (4)
S1—O21.421 (3)C16—H160.9300
S1—O41.427 (2)C17—C181.371 (4)
S1—C331.783 (4)C17—H170.9300
F1—C331.273 (5)C18—C191.366 (4)
F2—C331.298 (4)C18—H180.9300
F3—C331.354 (5)C19—C201.380 (4)
O1—C21.212 (3)C19—H190.9300
C1—C21.519 (3)C20—H200.9300
C1—H1A0.9700C21—C261.387 (3)
C1—H1B0.9700C21—C221.388 (3)
C2—C31.477 (3)C22—C231.373 (4)
C3—C41.385 (3)C22—H220.9300
C3—C81.391 (3)C23—C241.363 (5)
C4—C51.385 (3)C23—H230.9300
C4—H40.9300C24—C251.374 (4)
C5—C61.387 (3)C24—H240.9300
C5—H50.9300C25—C261.380 (4)
C6—C71.394 (3)C25—H250.9300
C6—C91.477 (3)C26—H260.9300
C7—C81.361 (3)C27—C281.382 (3)
C7—H70.9300C27—C321.395 (3)
C8—H80.9300C28—C291.385 (3)
C9—C101.388 (3)C28—H280.9300
C9—C141.389 (3)C29—C301.368 (4)
C10—C111.378 (4)C29—H290.9300
C10—H100.9300C30—C311.371 (4)
C11—C121.374 (4)C30—H300.9300
C11—H110.9300C31—C321.376 (3)
C12—C131.365 (4)C31—H310.9300
C12—H120.9300C32—H320.9300
C13—C141.382 (4)
C21—P1—C15111.69 (11)C16—C15—P1119.27 (19)
C21—P1—C27106.52 (10)C17—C16—C15120.0 (3)
C15—P1—C27108.17 (11)C17—C16—H16120.0
C21—P1—C1109.71 (11)C15—C16—H16120.0
C15—P1—C1111.96 (11)C18—C17—C16119.5 (3)
C27—P1—C1108.60 (11)C18—C17—H17120.3
O3—S1—O2113.5 (2)C16—C17—H17120.3
O3—S1—O4113.63 (16)C19—C18—C17121.2 (3)
O2—S1—O4116.7 (2)C19—C18—H18119.4
O3—S1—C33104.93 (19)C17—C18—H18119.4
O2—S1—C33102.5 (2)C18—C19—C20119.9 (3)
O4—S1—C33103.55 (16)C18—C19—H19120.0
C2—C1—P1111.90 (16)C20—C19—H19120.0
C2—C1—H1A109.2C19—C20—C15120.0 (3)
P1—C1—H1A109.2C19—C20—H20120.0
C2—C1—H1B109.2C15—C20—H20120.0
P1—C1—H1B109.2C26—C21—C22119.7 (2)
H1A—C1—H1B107.9C26—C21—P1118.85 (18)
O1—C2—C3122.0 (2)C22—C21—P1121.1 (2)
O1—C2—C1119.1 (2)C23—C22—C21119.4 (3)
C3—C2—C1118.8 (2)C23—C22—H22120.3
C4—C3—C8118.4 (2)C21—C22—H22120.3
C4—C3—C2123.7 (2)C24—C23—C22121.0 (3)
C8—C3—C2117.9 (2)C24—C23—H23119.5
C5—C4—C3120.6 (2)C22—C23—H23119.5
C5—C4—H4119.7C23—C24—C25120.0 (3)
C3—C4—H4119.7C23—C24—H24120.0
C4—C5—C6120.9 (2)C25—C24—H24120.0
C4—C5—H5119.6C24—C25—C26120.2 (3)
C6—C5—H5119.6C24—C25—H25119.9
C5—C6—C7117.7 (2)C26—C25—H25119.9
C5—C6—C9122.2 (2)C25—C26—C21119.7 (2)
C7—C6—C9120.1 (2)C25—C26—H26120.2
C8—C7—C6121.5 (2)C21—C26—H26120.2
C8—C7—H7119.2C28—C27—C32119.7 (2)
C6—C7—H7119.2C28—C27—P1121.99 (18)
C7—C8—C3120.8 (2)C32—C27—P1117.89 (17)
C7—C8—H8119.6C27—C28—C29119.7 (2)
C3—C8—H8119.6C27—C28—H28120.1
C10—C9—C14117.9 (2)C29—C28—H28120.1
C10—C9—C6122.2 (2)C30—C29—C28120.3 (2)
C14—C9—C6119.9 (2)C30—C29—H29119.9
C11—C10—C9120.7 (3)C28—C29—H29119.9
C11—C10—H10119.7C29—C30—C31120.2 (2)
C9—C10—H10119.7C29—C30—H30119.9
C12—C11—C10120.3 (3)C31—C30—H30119.9
C12—C11—H11119.8C30—C31—C32120.6 (2)
C10—C11—H11119.8C30—C31—H31119.7
C13—C12—C11119.9 (3)C32—C31—H31119.7
C13—C12—H12120.1C31—C32—C27119.5 (2)
C11—C12—H12120.1C31—C32—H32120.3
C12—C13—C14120.1 (3)C27—C32—H32120.3
C12—C13—H13119.9F1—C33—F2109.2 (4)
C14—C13—H13119.9F1—C33—F3105.9 (4)
C13—C14—C9120.9 (2)F2—C33—F3104.8 (4)
C13—C14—H14119.5F1—C33—S1114.5 (3)
C9—C14—H14119.5F2—C33—S1112.4 (3)
C20—C15—C16119.4 (2)F3—C33—S1109.3 (3)
C20—C15—P1121.34 (19)

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C21–C26 and C15–C20 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
C1—H1B···O4i0.972.223.191 (4)178
C26—H26···O3ii0.932.453.373 (3)174
C32—H32···O3ii0.932.463.369 (4)168
C1—H1A···Cg1iii0.972.843.780 (3)164
C10—H10···Cg2iv0.933.023.767 (4)138
C23—H23···Cg3v0.932.913.788 (4)159

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, −y+1, −z; (iv) −x, y+1/2, −z+1/2; (v) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2176).

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