A dinuclear rhenium complex, {[(C18H24N2)Re(CO)3]2(μ C12H12N2)}(PF6)2·2CH2Cl2

metal-organic papers

m134

S.-S. Sunet al. [Re(C₁₂H₁₂N₂)(C₁₈H₂₄N₂)₂(CO)₆](PF₆)₂.2CH₂Cl₂DOI: 10.1107/S1600536803004094Acta Cryst.(2003). E59, m134±m136 Acta Crystallographica Section E

Structure Reports Online

ISSN 1600-5368

A dinuclear rhenium complex, {[(C

18

H

24

N

2

)-Re(CO)

3

]

2

(

l

-C

12

H

12

N

2

)}(PF

6

)

2

2CH

2

Cl

2

Shih-Sheng Sun,a_{Dat T. Tran,}a Peter Y. Zavalij,a,b_{Scott R. J.} Olivera_{* and Alistair J. Lees}a

a_{Department of Chemistry, State University}

of New York at Binghamton, Binghamton, NY 13902-6000, USA, andb_{Institute for} Materials Research, State University of New York at Binghamton, Binghamton, NY 13902-6000, USA

Correspondence e-mail: [email protected]

Key indicators Single-crystal X-ray study

T= 110 K

Mean(C±C) = 0.007 AÊ

Rfactor = 0.035

wRfactor = 0.099

Data-to-parameter ratio = 19.6

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2003 International Union of Crystallography Printed in Great Britain ± all rights reserved

A new ReI_{complex has been synthesized by re¯ux methods,}

viz. -ethylene-1,2-di-4-pyridyl-2_N:N0_-bis[fac

-tricarbonyl-(4,40_{-tert-butyl-2,2}0_{-bipyridine)rhenium(I)]}

hexa¯uorophos-phate dichloromethane disolvate, [Re(-C12H12N2)(C18H24 -N2)2(CO)6](PF6)22CH2Cl2. The compound is a centrosym-metric dinuclear complex. The self-assembled structure contains octahedral Re centers, connected by a 1,2-bis(4-pyridyl)ethylene linking group.

Comment

The photochemistry and photophysics of diimine±ReI_± carbonyl complexes are well established (Tapolsky & Meyer, 1990). Many of these complexes exhibit a variety of accessible excited states, including metal-to-ligand charge transfer (MLCT), ligand-to-ligand charge transfer (LLCT) and intra-ligand (IL) states. The nature of the lowest energy excited state usually plays a decisive role in the resulting photo-physical and photochemical properties (Sun & Lees, 2000a).

Diimine±ReI_{±carbonyl complexes, in particular, typically} possess lowest MLCT excited states, with long-lived excited state lifetimes. They are, therefore, promising candidates for developing highly sensitive luminescent sensing materials (Sun & Lees, 2000b). The facial modi®cation of the ancillary and bridging ligands allows the modular design and ®ne tuning of their ground- and excited-state properties (Sun & Lees, 2002).

We report here a new centrosymmetric dinuclear Re complex, (I), where the octahedral metal centers are connected by 1,2-bis(4-pyridyl)ethylene (BPA, Fig. 1). For each metal of the cation, a bidentate 4,40_{-di-tert-butyl-2,2}0

-bi-pyridine ligand occupies the cis positions relative to the linking sites. Threetranscarbonyl groups complete the octa-hedral coordination of the Re atoms.

The complex cations are aligned approximately along [101], with hexa¯uorophosphate anions and dichloromethane mol-ecules residing between them (Fig. 2). The PF6ÿ anions charge-balance the divalent cationic charge of the complex. This structure opens up new possibilities in creating oligo-meric, cyclic and cage-like organometallic molecules. Such

structures, with accessible well-de®ned voids, may lead to various host±guest applications, such as sensing or catalysis.

Experimental

To a 100 ml ¯ask containing (4,40_-t_Bu

2bpy)Re(CO)3(CH3CN)(PF6)

(100 mg, 0.14 mmol) and 1,2-bis(4-pyridyl)ethane (BPA, 12 mg, 0.065 mmol) was added 30 ml of tetrahydrofuran. The resulting mixture was re¯uxed for 16 h. Subsequently, the solution was cooled to room temperature and the solvent removed under reduced pres-sure. The residue was dissolved in 20 ml CH2Cl2 and ®ltered to

remove any undissolved material. The ®ltrate was layered with 100 ml hexane and allowed to stand for 2 d to afford yellow microcrystals (yield: 86%). IR (C=O, CH2Cl2): 2033, 1929; 1H NMR (300 MHz,

acetone-d6):9.28 (d, 4H,3JHÐH= 5.9 Hz, H6,60±Bu₂bpy), 8.72 (d, 4H, 4_J

HÐH= 1.7 Hz, H3,30±Bu₂bpy), 8.37 (d, 4H,3J_HÐH= 6.5 Hz, H-py),

7.95 (d, 4H, 3_J

HÐH = 5.9 Hz,4JHÐH = 1.9 Hz, H5,50±Bu₂bpy), 7.35

(d, 4H,3_J

HÐH= 6.5 Hz, H-py), 2.90 (s, 4H, ÐCH2Ð), 1.42 (s, 72H,

ÐCH3);13C NMR (acetone-d6):196.8, 192.9, 167.1, 156.9, 155.8,

154.5, 152.8, 127.7, 127.0, 123.1, 36.8, 34.9; ES±MS: m/z = 1407.5 (calculated m/z = 1407.3 for [M-PF6ÿ]+). Analysis calculated for

C54H60N6O6Re2P2F12: C 41.81, H 3.90, N 5.42%; found: C 41.87, H

3.79, N, 5.52%.

Crystal data

[Re(C12H12N2)(C18H24N2)2 -(CO)6](PF6)22CH2Cl2 Mr= 1721.28

Monoclinic,P21=n a= 12.0280 (7) AÊ b= 10.2060 (6) AÊ c= 26.1366 (14) AÊ = 95.695 (2) V= 3192.6 (3) AÊ3 Z= 2

Dx= 1.791 Mg mÿ3

MoKradiation Cell parameters from 6778

re¯ections = 5.1±62.8

= 4.09 mmÿ1 T= 110 K Prism, light yellow 0.350.240.18 mm

Data collection

Bruker SMART Apex CCD diffractometer

!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin= 0.342,Tmax= 0.479 32788 measured re¯ections

7907 independent re¯ections 7044 re¯ections withI> 2(I) Rint= 0.033

max= 28.3 h=ÿ16!15 k=ÿ13!13 l=ÿ34!34

Re®nement

Re®nement onF2 R[F2_{> 2(F}2_{)] = 0.035} wR(F2_{) = 0.099} S= 1.05 7907 re¯ections 403 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0534P)2

+ 12.0416P]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.003 max= 2.62 e AÊÿ3 min=ÿ1.61 e AÊÿ3

Table 1

Selected geometric parameters (AÊ,_). Re1ÐC2 1.922 (4) Re1ÐC1 1.932 (4) Re1ÐC3 1.939 (4) Re1ÐN2 2.164 (3)

Re1ÐN3 2.167 (3) Re1ÐN1 2.220 (4) C9ÐC9i _{1.495 (10)}

C3ÐRe1ÐN2 172.47 (15)

C2ÐRe1ÐN3 170.71 (16) C1ÐRe1ÐN1 179.27 (16) N2ÐC14ÐC15ÐN3 ÿ0.4 (5)

C11ÐC12ÐC20ÐC21 2.5 (6) C18ÐC17ÐC24ÐC27 179.7 (5)

Symmetry code: (i)ÿx;ÿy;2ÿz.

All H atoms were included in calculated positions, with CÐH distances of 0.93±0.97 AÊ. They were included in the re®nement in riding-motion approximation with Uiso= 1.2Ueq(Uiso= 1.5Ueqfor

methyl) of the carrier atom. The maximum electron-density peak is located in the vicinity of the Re1 atom.

Data collection:SMART(Bruker, 1999); cell re®nement:SAINT

(Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

ORTEP-3 (Farrugia, 1997) and ATOMS (Dowty, 1999); software used to prepare material for publication:SHELXL97.

This work was supported by The Division of Chemical Sciences, Of®ce of Basic Energy Sciences, Of®ce of Science, US Department of Energy (grant No. DE-FG02-89ER14039).

Acta Cryst.(2003). E59, m134±m136 S.-S. Sunet al. [Re(C₁₂H₁₂N₂)(C₁₈H₂₄N₂)₂(CO)₆](PF₆)₂.2CH₂Cl₂

m135

metal-organic papers

Figure 2

The crystallographic b-projection, showing PF6 ions and CH2Cl2 molecules between the cations (colour scheme: Re purple, N dark blue, C green, Cl green, O red, F yellow, and P light blue).

Figure 1

metal-organic papers

m136

S.-S. Sunet al. [Re(C₁₂H₁₂N₂)(C₁₈H₂₄N₂)₂(CO)₆](PF₆)₂.2CH₂Cl₂ Acta Cryst.(2003). E59, m134±m136

References

Bruker (1999).SMARTandSAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Dowty, E. (1999).ATOMS for Windows and Macintosh. Version 5. Shape Software, 521 Hidden Valley Road, Kingsport, TN 37663, USA.

Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.

Sheldrick, G. M. (1990).Acta Cryst.A46, 467±473.

Sheldrick, G. M. (1996).SADABS. University of GoÈttingen, Germany. Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Sun, S.-S. & Lees, A. J. (2000a).J. Am. Chem. Soc.122, 8956±8967. Sun, S.-S. & Lees, A. J. (2000b).Chem. Commun.pp. 1687±1688. Sun, S.-S. & Lees, A. J. (2002).Coord. Chem. Rev.230, 171±192.

supporting information

sup-1 Acta Cryst. (2003). E59, m134–m136

supporting information

Acta Cryst. (2003). E59, m134–m136 [https://doi.org/10.1107/S1600536803004094]

A dinuclear rhenium complex, {[(C

18

H

24

N

2

)Re(CO)

3

]

2

(

µ

-C

12

H

12

N

2

)}

(PF

6

)

2

·

2CH

2

Cl

2

Shih-Sheng Sun, Dat T. Tran, Peter Y. Zavalij, Scott R. J. Oliver and Alistair J. Lees

µ-ethylene-1,2-di-4-pyridyl-κ2_{N:N′-bis[fac-tricarbonyl(4,4′-tert-butyl- 2,2′-bipyridine)rhenium(I)]}

hexafluorophosphate dichloromethane solvate

Crystal data

[Re(C12H12N2)(C18H24N2)2(CO)6](PF6)2·2CH2Cl2 Mr = 1721.28

Monoclinic, P21/n Hall symbol: -P 2yn a = 12.0280 (7) Å b = 10.2060 (6) Å c = 26.1366 (14) Å β = 95.695 (2)° V = 3192.6 (3) Å3 Z = 2

F(000) = 1692 Dx = 1.791 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 6778 reflections θ = 5.1–62.8°

µ = 4.09 mm−1 T = 110 K

Prism, light yellow 0.35 × 0.24 × 0.18 mm

Data collection

Bruker SMART Apex CCD diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.342, Tmax = 0.479

32788 measured reflections 7907 independent reflections 7044 reflections with I > 2σ(I) Rint = 0.033

θmax = 28.3°, θmin = 1.8° h = −16→15

k = −13→13 l = −34→34

Refinement Refinement on F2 Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.035} wR(F2_{) = 0.099} S = 1.05 7907 reflections 403 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(F

o2) + (0.0534P)2 + 12.0416P] where P = (Fo2 + 2Fc2)/3

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sup-2 Acta Cryst. (2003). E59, m134–m136

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 F}2_, conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

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sup-3 Acta Cryst. (2003). E59, m134–m136

H18 0.5295 0.5218 0.9082 0.027* C19 0.4051 (3) 0.4337 (4) 0.86351 (16) 0.0217 (8) H19 0.4469 0.3602 0.8567 0.026* C20 −0.1429 (4) 0.7596 (5) 0.82037 (19) 0.0273 (9) C21 −0.2608 (4) 0.7318 (6) 0.7947 (2) 0.0337 (11) H21A −0.2882 0.6518 0.8082 0.051* H21B −0.2585 0.7233 0.7583 0.051* H21C −0.3096 0.8027 0.8017 0.051* C22 −0.0983 (4) 0.8851 (5) 0.7969 (2) 0.0381 (12) H22A −0.1477 0.9567 0.8020 0.057* H22B −0.0942 0.8723 0.7607 0.057* H22C −0.0252 0.9045 0.8133 0.057* C23 −0.1480 (5) 0.7800 (6) 0.8781 (2) 0.0375 (12) H23A −0.1748 0.7014 0.8930 0.056* H23B −0.1977 0.8511 0.8835 0.056* H23C −0.0747 0.8001 0.8941 0.056* C24 0.4519 (4) 0.7553 (5) 0.93672 (18) 0.0262 (9) C25 0.4925 (6) 0.7007 (6) 0.9904 (2) 0.0444 (14) H25A 0.5283 0.7693 1.0111 0.067* H25B 0.5447 0.6309 0.9869 0.067* H25C 0.4298 0.6681 1.0065 0.067* C26 0.5525 (6) 0.8042 (6) 0.9104 (3) 0.0463 (15) H26A 0.5277 0.8342 0.8763 0.069* H26B 0.6049 0.7339 0.9083 0.069* H26C 0.5879 0.8750 0.9299 0.069* C27 0.3723 (5) 0.8697 (6) 0.9431 (3) 0.0490 (15) H27A 0.4107 0.9366 0.9638 0.073* H27B 0.3093 0.8394 0.9597 0.073* H27C 0.3470 0.9050 0.9099 0.073* P1 0.67141 (12) 0.19133 (14) 0.87212 (6) 0.0349 (3) F1 0.6693 (3) 0.3340 (4) 0.89769 (16) 0.0600 (10) F2 0.7363 (3) 0.1347 (4) 0.92414 (14) 0.0565 (10) F3 0.7890 (3) 0.2230 (4) 0.85094 (16) 0.0566 (10) F4 0.6720 (3) 0.0496 (4) 0.84669 (15) 0.0549 (9) F5 0.6071 (3) 0.2484 (4) 0.82040 (13) 0.0441 (8) F6 0.5547 (3) 0.1604 (4) 0.89377 (13) 0.0437 (8) C28 0.8517 (8) 0.4152 (9) 0.9797 (4) 0.080 (3) H28A 0.7971 0.3521 0.9651 0.096* H28B 0.8971 0.4417 0.9528 0.096* Cl1 0.93614 (16) 0.3422 (2) 1.02952 (8) 0.0671 (5) Cl2 0.7824 (2) 0.5526 (2) 1.00162 (13) 0.0985 (9)

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

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sup-4 Acta Cryst. (2003). E59, m134–m136

C2 0.023 (2) 0.0205 (19) 0.022 (2) 0.0017 (16) 0.0021 (16) −0.0004 (16) O2 0.0277 (17) 0.0320 (18) 0.0331 (18) −0.0034 (14) −0.0004 (14) −0.0078 (14) C3 0.0198 (19) 0.024 (2) 0.025 (2) −0.0015 (16) 0.0013 (16) −0.0038 (16) O3 0.0254 (16) 0.0280 (17) 0.0393 (19) 0.0074 (13) −0.0028 (14) −0.0086 (14) C4 0.026 (2) 0.030 (2) 0.027 (2) −0.0005 (18) −0.0020 (18) 0.0052 (18) N1 0.0207 (17) 0.0217 (17) 0.0226 (17) 0.0025 (13) −0.0010 (14) −0.0003 (13) C5 0.029 (2) 0.035 (2) 0.028 (2) −0.001 (2) −0.0043 (18) 0.0072 (19) C6 0.026 (2) 0.035 (2) 0.023 (2) −0.0019 (18) 0.0003 (17) 0.0043 (18) C7 0.023 (2) 0.043 (3) 0.030 (2) −0.003 (2) 0.0031 (18) 0.010 (2) C8 0.029 (2) 0.033 (2) 0.024 (2) −0.0024 (18) 0.0026 (18) 0.0039 (18) C9 0.032 (3) 0.046 (3) 0.023 (2) −0.002 (2) 0.0020 (19) 0.010 (2) N2 0.0178 (16) 0.0218 (17) 0.0169 (15) 0.0003 (13) 0.0000 (12) −0.0001 (13) N3 0.0164 (15) 0.0196 (17) 0.0212 (16) 0.0003 (13) 0.0022 (13) −0.0011 (13) C10 0.022 (2) 0.023 (2) 0.025 (2) −0.0007 (16) −0.0030 (16) −0.0029 (16) C11 0.0183 (19) 0.027 (2) 0.027 (2) 0.0003 (16) −0.0020 (16) −0.0002 (17) C12 0.0181 (19) 0.025 (2) 0.023 (2) 0.0063 (16) 0.0006 (15) 0.0001 (16) C13 0.0175 (19) 0.022 (2) 0.025 (2) 0.0015 (15) 0.0013 (15) −0.0022 (16) C14 0.0168 (18) 0.0212 (19) 0.0175 (18) 0.0004 (15) 0.0028 (14) 0.0014 (15) C15 0.0148 (17) 0.0208 (19) 0.0196 (18) 0.0007 (14) 0.0026 (14) 0.0005 (15) C16 0.0198 (19) 0.021 (2) 0.0228 (19) 0.0010 (15) 0.0012 (15) −0.0018 (15) C17 0.0208 (19) 0.024 (2) 0.0178 (18) −0.0018 (16) 0.0005 (15) −0.0007 (15) C18 0.0160 (18) 0.028 (2) 0.024 (2) 0.0022 (16) −0.0001 (15) −0.0002 (17) C19 0.0183 (19) 0.022 (2) 0.025 (2) 0.0052 (15) 0.0001 (15) 0.0011 (16) C20 0.019 (2) 0.031 (2) 0.031 (2) 0.0097 (18) −0.0015 (17) −0.0029 (19) C21 0.020 (2) 0.043 (3) 0.037 (3) 0.009 (2) −0.0027 (19) −0.005 (2) C22 0.034 (3) 0.029 (3) 0.052 (3) 0.008 (2) 0.001 (2) −0.001 (2) C23 0.031 (3) 0.051 (3) 0.031 (3) 0.017 (2) 0.001 (2) −0.007 (2) C24 0.022 (2) 0.027 (2) 0.029 (2) −0.0033 (17) −0.0004 (17) −0.0071 (18) C25 0.050 (3) 0.046 (3) 0.034 (3) −0.001 (3) −0.010 (3) −0.007 (2) C26 0.046 (3) 0.042 (3) 0.053 (4) −0.018 (3) 0.010 (3) −0.005 (3) C27 0.040 (3) 0.039 (3) 0.064 (4) 0.002 (2) −0.011 (3) −0.024 (3) P1 0.0293 (6) 0.0424 (8) 0.0330 (7) 0.0142 (5) 0.0026 (5) 0.0008 (5) F1 0.060 (2) 0.052 (2) 0.065 (3) 0.0078 (19) −0.0077 (19) −0.0170 (19) F2 0.0414 (19) 0.084 (3) 0.0429 (19) 0.0211 (19) −0.0013 (15) 0.0160 (19) F3 0.0306 (17) 0.077 (3) 0.062 (2) 0.0101 (17) 0.0073 (16) 0.018 (2) F4 0.063 (2) 0.047 (2) 0.056 (2) 0.0194 (18) 0.0135 (18) −0.0058 (17) F5 0.0368 (17) 0.0559 (19) 0.0386 (17) 0.0125 (16) −0.0008 (14) 0.0077 (16) F6 0.0353 (17) 0.057 (2) 0.0395 (17) 0.0129 (15) 0.0069 (13) 0.0026 (15) C28 0.083 (6) 0.064 (5) 0.084 (6) 0.005 (4) −0.035 (5) 0.002 (4) Cl1 0.0579 (10) 0.0827 (13) 0.0602 (11) 0.0101 (9) 0.0035 (8) 0.0113 (10) Cl2 0.0854 (16) 0.0706 (14) 0.145 (2) 0.0225 (12) 0.0412 (16) 0.0296 (15)

Geometric parameters (Å, º)

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sup-5 Acta Cryst. (2003). E59, m134–m136

Re1—N3 2.167 (3) C19—H19 0.9300 Re1—N1 2.220 (4) C20—C23 1.531 (7) C1—O1 1.138 (5) C20—C21 1.534 (7) C2—O2 1.152 (5) C20—C22 1.539 (8) C3—O3 1.143 (5) C21—H21A 0.9600 C4—N1 1.347 (6) C21—H21B 0.9600 C4—C5 1.378 (7) C21—H21C 0.9600 C4—H4 0.9300 C22—H22A 0.9600 N1—C6 1.321 (6) C22—H22B 0.9600 C5—C8 1.373 (7) C22—H22C 0.9600 C5—H5 0.9300 C23—H23A 0.9600 C6—C7 1.378 (6) C23—H23B 0.9600 C6—H6 0.9300 C23—H23C 0.9600 C7—C8 1.390 (7) C24—C27 1.529 (7) C7—H7 0.9300 C24—C26 1.534 (7) C8—C9 1.510 (6) C24—C25 1.542 (7) C9—C9i _{1.495 (10) C25—H25A 0.9600} C9—H9A 0.9700 C25—H25B 0.9600 C9—H9B 0.9700 C25—H25C 0.9600 N2—C10 1.340 (5) C26—H26A 0.9600 N2—C14 1.358 (5) C26—H26B 0.9600 N3—C19 1.348 (5) C26—H26C 0.9600 N3—C15 1.355 (5) C27—H27A 0.9600 C10—C11 1.378 (6) C27—H27B 0.9600 C10—H10 0.9300 C27—H27C 0.9600 C11—C12 1.388 (6) P1—F4 1.592 (4) C11—H11 0.9300 P1—F6 1.597 (4) C12—C13 1.396 (6) P1—F5 1.599 (3) C12—C20 1.540 (6) P1—F3 1.602 (4) C13—C14 1.384 (6) P1—F1 1.603 (4) C13—H13 0.9300 P1—F2 1.607 (4) C14—C15 1.484 (5) C28—Cl1 1.738 (8) C15—C16 1.389 (6) C28—Cl2 1.757 (10) C16—C17 1.393 (6) C28—H28A 0.9700 C16—H16 0.9300 C28—H28B 0.9700

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sup-6 Acta Cryst. (2003). E59, m134–m136

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sup-7 Acta Cryst. (2003). E59, m134–m136

N2—C14—C13 121.3 (4) F5—P1—F1 89.7 (2) N2—C14—C15 115.1 (3) F3—P1—F1 90.7 (2) C13—C14—C15 123.5 (4) F4—P1—F2 90.3 (2) N3—C15—C16 121.7 (4) F6—P1—F2 89.97 (19) N3—C15—C14 115.0 (4) F5—P1—F2 179.7 (3) C16—C15—C14 123.3 (4) F3—P1—F2 89.6 (2) C15—C16—C17 121.0 (4) F1—P1—F2 90.0 (2) C15—C16—H16 119.5 Cl1—C28—Cl2 111.0 (5) C17—C16—H16 119.5 Cl1—C28—H28A 109.4 C16—C17—C18 116.4 (4) Cl2—C28—H28A 109.4 C16—C17—C24 122.8 (4) Cl1—C28—H28B 109.4 C18—C17—C24 120.7 (4) Cl2—C28—H28B 109.4 C19—C18—C17 120.1 (4) H28A—C28—H28B 108.0 C19—C18—H18 120.0

supporting information

sup-8 Acta Cryst. (2003). E59, m134–m136

C3—Re1—N3—C15 −176.4 (3) C18—C17—C24—C27 179.7 (5) N2—Re1—N3—C15 −1.0 (3) C16—C17—C24—C26 −120.1 (5) N1—Re1—N3—C15 −86.9 (3) C18—C17—C24—C26 58.7 (6) C14—N2—C10—C11 −0.3 (6) C16—C17—C24—C25 121.1 (5) Re1—N2—C10—C11 −179.9 (3) C18—C17—C24—C25 −60.1 (6) N2—C10—C11—C12 1.0 (7) C8—C9—C9i_—C8i _{180.000 (3)} C10—C11—C12—C13 −0.6 (6)