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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page m1337
https://doi.org/10.1107/S1600536811035811

Di­bromidooxido[(Z)-N′-(propan-2-yl­­idene)benzohydrazidato](tri­phenyl­phosphane)rhenium(V)

Nonzaliseko Yumata,a Thomas Gerbera and Richard Betza*

aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
*Correspondence e-mail: richard.betz@webmail.co.za

(Received 18 August 2011; accepted 2 September 2011; online 14 September 2011)

The asymmetric unit of the title neutral rhenium(V) coordination compound, [ReBr2(C10H11N2O)O(C18H15P)], contains two mol­ecules. In each of the two molecules the metal atom is octa­hedrally coordinated, the bromido ligands being cis-orientated. The chelate ligand is present in its imine-tautomeric form. In the crystal, C—H⋯Br contacts connect the mol­ecules into chains along [101]. The shortest inter­centroid distance between two aromatic rings was found to be 3.906 (2) Å.

Related literature

For the crystal structures of rhenium(I), rhenium(III) and rhenium(V) metal complexes featuring tridentate ONX (X = O, N, S)-donor Schiff bases, see: Potgieter et al. (2010[Potgieter, K. C., Gerber, T. I. A. & Mayer, P. (2010). Polyhedron, 29, 1423-1430.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For general information about radiopharmaceuticals, see: Gerber et al. (2011[Gerber, T. I. A., Betz, R., Booysen, I. N., Potgieter, K. C. & Mayer, P. (2011). Polyhedron, 30, 1739-1745.]).

[Scheme 1]

Experimental

Crystal data

  • [ReBr2(C10H11N2O)O(C18H15P)]

  • Mr = 799.50

  • Monoclinic, P 21 /c

  • a = 19.1130 (5) Å

  • b = 18.3910 (4) Å

  • c = 15.8140 (4) Å

  • β = 97.410 (1)°

  • V = 5512.3 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 7.40 mm−1

  • T = 200 K

  • 0.39 × 0.35 × 0.16 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.589, Tmax = 1.000

  • 50272 measured reflections

  • 13695 independent reflections

  • 11062 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.066

  • S = 1.11

  • 13695 reflections

  • 649 parameters

  • H-atom parameters constrained

  • Δρmax = 1.11 e Å−3

  • Δρmin = −1.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C22—H22⋯Br3 0.95 2.94 3.819 (5) 154
C85—H85⋯Br2i 0.95 2.92 3.587 (4) 128
Symmetry code: (i) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811035811/ff2026sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035811/ff2026Isup2.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035811/ff2026Isup3.hkl

checkCIF report


Comment top

Next to cardiovascular diseases, cancer has become one of the main fatal diseases in industrialized countries. Apart from classical surgery, chemo- and radiotherapeutic treatments have entered the arsenal of possible cures for certain types of cancer. All methods, however, suffer from their own set of problematic side-effects and, as a consequence, the development of radiopharmaceuticals – combining the advantages of chemotherapy as well as radiation methods while at the same time avoiding their unique respective undesired side-effects – has been a topic of research (Gerber et al., 2011). Tailoring and fine-tuning of the envisioned radiopharmaceuticals' properties such as lipophilicity and, in particular, inertness is of paramount importance with respect to possible future in vivo applications in contemporary medicine and requires sound knowledge about structural parameters of the ligands applied if a more heuristic approach in the synthesis is to triumph over pure trial-and-error as it is encountered in this specific field of coordination chemistry up to the present day. In continuation of our interest in rhenium-based coordination compounds that might serve as radiopharmaceuticals, we determined the molecular and crystal structure of the title compound. Information about the crystal structures of rhenium coordination compounds with the central atom in different oxidation states is apparent in the literature (Potgieter et al., 2010).

The central atom in both molecules of the asymmetric unit is hexacoordinate. The ligand sphere features one chelate ligand which is present in its tautomeric imine form. Both oxygen atoms are in trans-position, the bromido ligands are cis-orientated. While the small puckering amplitude of one of the five-membered chelate rings (τ = 4.3 °) precludes a conformational analysis (Cremer & Pople, 1975) in the first molecule of the asymmetric unite, the corresponding five-membered ring in the second molecule adopts an envelope conformation on the rhenium atom (Re2E, Q2 = 0.076 (3) Å, π2 = 358 (3) °). The central atom is displaced by 0.184 (1) Å and 0.188 (1) Å, respectively, from the plane defined by the bromido ligands as well as the coordinating nitrogen atom and phosphorus atom (Fig. 1).

In the crystal, C–H···Br contacts can be observed whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the respective atoms. These are supported exclusively by hydrogen atoms of phenyl groups on the triphenylphosphane ligand and involve hydrogen atoms in ortho as well as in meta position as donors and the bromido ligand in trans-position to the coordinating phosphorus atom as acceptors. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is DD on the unitary level. In total, the molecules are connected to chains along [1 0 1] (Fig. 2). The shortest intercentroid distance between two centers of gravity was found at 3.906 (2) Å.

Related literature top

For the crystal structures of rhenium(I), rhenium(III) and rhenium(V) metal complexes featuring tridentate ONX (X = O, N, S)-donor Schiff bases, see: Potgieter et al. (2010). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For puckering analysis, see: Cremer & Pople (1975). For general information about radiopharmaceuticals, see: Gerber et al. (2011).

Experimental top

Benzhydrazide and trans-[ReOBr3(PPh3)2] were refluxed in acetone for 5 h. After cooling to room temperature and filtration the filtrate was stored at room temperature upon which crystals formed in the course of a couple of days.

Refinement top

Carbon-bound H atoms were placed in calculated positions (C—H 0.95 Å for aromatic C atoms, C—H 0.98 Å for methyl groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C) for aromatic carbon atoms and U(H) set to 1.5Ueq(C) for methyl groups.

Structure description top

Next to cardiovascular diseases, cancer has become one of the main fatal diseases in industrialized countries. Apart from classical surgery, chemo- and radiotherapeutic treatments have entered the arsenal of possible cures for certain types of cancer. All methods, however, suffer from their own set of problematic side-effects and, as a consequence, the development of radiopharmaceuticals – combining the advantages of chemotherapy as well as radiation methods while at the same time avoiding their unique respective undesired side-effects – has been a topic of research (Gerber et al., 2011). Tailoring and fine-tuning of the envisioned radiopharmaceuticals' properties such as lipophilicity and, in particular, inertness is of paramount importance with respect to possible future in vivo applications in contemporary medicine and requires sound knowledge about structural parameters of the ligands applied if a more heuristic approach in the synthesis is to triumph over pure trial-and-error as it is encountered in this specific field of coordination chemistry up to the present day. In continuation of our interest in rhenium-based coordination compounds that might serve as radiopharmaceuticals, we determined the molecular and crystal structure of the title compound. Information about the crystal structures of rhenium coordination compounds with the central atom in different oxidation states is apparent in the literature (Potgieter et al., 2010).

The central atom in both molecules of the asymmetric unit is hexacoordinate. The ligand sphere features one chelate ligand which is present in its tautomeric imine form. Both oxygen atoms are in trans-position, the bromido ligands are cis-orientated. While the small puckering amplitude of one of the five-membered chelate rings (τ = 4.3 °) precludes a conformational analysis (Cremer & Pople, 1975) in the first molecule of the asymmetric unite, the corresponding five-membered ring in the second molecule adopts an envelope conformation on the rhenium atom (Re2E, Q2 = 0.076 (3) Å, π2 = 358 (3) °). The central atom is displaced by 0.184 (1) Å and 0.188 (1) Å, respectively, from the plane defined by the bromido ligands as well as the coordinating nitrogen atom and phosphorus atom (Fig. 1).

In the crystal, C–H···Br contacts can be observed whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the respective atoms. These are supported exclusively by hydrogen atoms of phenyl groups on the triphenylphosphane ligand and involve hydrogen atoms in ortho as well as in meta position as donors and the bromido ligand in trans-position to the coordinating phosphorus atom as acceptors. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is DD on the unitary level. In total, the molecules are connected to chains along [1 0 1] (Fig. 2). The shortest intercentroid distance between two centers of gravity was found at 3.906 (2) Å.

For the crystal structures of rhenium(I), rhenium(III) and rhenium(V) metal complexes featuring tridentate ONX (X = O, N, S)-donor Schiff bases, see: Potgieter et al. (2010). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For puckering analysis, see: Cremer & Pople (1975). For general information about radiopharmaceuticals, see: Gerber et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
[Figure 2] Fig. 2. Intermolecular contacts, viewed along [0 0 - 1]. Symmetry operators: i x - 1, -y + 1/2, z - 1/2; ii x + 1, -y + 1/2, z + 1/2.
Dibromidooxido[(Z)-N'-(propan-2- ylidene)benzohydrazidato](triphenylphosphane)rhenium(V) top
Crystal data top
[ReBr2(C10H11N2O)O(C18H15P)]F(000) = 3072
Mr = 799.50Dx = 1.927 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 9749 reflections
a = 19.1130 (5) Åθ = 2.9–28.3°
b = 18.3910 (4) ŵ = 7.40 mm−1
c = 15.8140 (4) ÅT = 200 K
β = 97.410 (1)°Platelet, green
V = 5512.3 (2) Å30.39 × 0.35 × 0.16 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer		13695 independent reflections
Radiation source: fine-focus sealed tube11062 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −25→25
Tmin = 0.589, Tmax = 1.000k = −24→20
50272 measured reflectionsl = −21→20
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0171P)2 + 13.1603P]
where P = (Fo2 + 2Fc2)/3
13695 reflections(Δ/σ)max = 0.003
649 parametersΔρmax = 1.11 e Å−3
0 restraintsΔρmin = −1.33 e Å−3
Crystal data top
[ReBr2(C10H11N2O)O(C18H15P)]V = 5512.3 (2) Å3
Mr = 799.50Z = 8
Monoclinic, P21/cMo Kα radiation
a = 19.1130 (5) ŵ = 7.40 mm−1
b = 18.3910 (4) ÅT = 200 K
c = 15.8140 (4) Å0.39 × 0.35 × 0.16 mm
β = 97.410 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		13695 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		11062 reflections with I > 2σ(I)
Tmin = 0.589, Tmax = 1.000Rint = 0.031
50272 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.066H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0171P)2 + 13.1603P]
where P = (Fo2 + 2Fc2)/3
13695 reflectionsΔρmax = 1.11 e Å−3
649 parametersΔρmin = −1.33 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Re10.735701 (7)0.329200 (8)0.354383 (9)0.01810 (4)
Br10.79252 (2)0.26176 (2)0.24550 (3)0.02955 (9)
Br20.85659 (2)0.37295 (2)0.41703 (3)0.03182 (9)
P10.61621 (5)0.29731 (5)0.28519 (6)0.01951 (19)
O10.72398 (14)0.41638 (13)0.27545 (15)0.0217 (5)
O20.71940 (14)0.26514 (14)0.42482 (16)0.0255 (6)
N10.69989 (17)0.41714 (16)0.42803 (19)0.0214 (6)
N20.68319 (17)0.48183 (17)0.3824 (2)0.0241 (7)
C10.69745 (19)0.47580 (19)0.3050 (2)0.0201 (7)
C20.6947 (2)0.4213 (2)0.5092 (2)0.0289 (9)
C30.6707 (3)0.4897 (3)0.5471 (3)0.0453 (12)
H3110.70910.52540.55220.068*
H3210.65750.47940.60370.068*
H3310.62990.50930.51030.068*
C40.7118 (3)0.3590 (3)0.5684 (3)0.0494 (14)
H4110.67180.32520.56350.074*
H4210.72120.37700.62710.074*
H4310.75370.33380.55340.074*
C110.68113 (19)0.5372 (2)0.2456 (2)0.0218 (8)
C120.6662 (2)0.6056 (2)0.2763 (3)0.0278 (9)
H120.66820.61350.33590.033*
C130.6484 (2)0.6622 (2)0.2198 (3)0.0335 (10)
H130.63790.70890.24070.040*
C140.6458 (2)0.6509 (2)0.1333 (3)0.0356 (10)
H140.63380.68990.09480.043*
C150.6607 (2)0.5832 (2)0.1023 (3)0.0362 (10)
H150.65870.57570.04260.043*
C160.6784 (2)0.5264 (2)0.1581 (3)0.0289 (9)
H160.68880.47990.13680.035*
C210.5865 (2)0.3391 (2)0.1828 (2)0.0237 (8)
C220.5194 (2)0.3683 (3)0.1637 (3)0.0364 (10)
H220.48770.36770.20530.044*
C230.4984 (3)0.3984 (3)0.0841 (3)0.0475 (13)
H230.45250.41870.07140.057*
C240.5439 (3)0.3990 (3)0.0233 (3)0.0439 (12)
H240.52960.4203−0.03090.053*
C250.6101 (3)0.3688 (3)0.0409 (3)0.0394 (11)
H250.64110.3686−0.00150.047*
C260.6317 (2)0.3389 (2)0.1204 (3)0.0295 (9)
H260.67750.31820.13240.035*
C310.5533 (2)0.3228 (2)0.3572 (2)0.0235 (8)
C320.5277 (2)0.2710 (2)0.4097 (3)0.0333 (10)
H320.53900.22110.40360.040*
C330.4857 (3)0.2918 (3)0.4709 (3)0.0430 (12)
H330.46890.25640.50710.052*
C340.4686 (3)0.3640 (3)0.4792 (3)0.0429 (12)
H340.43940.37820.52050.051*
C350.4938 (2)0.4158 (3)0.4274 (3)0.0376 (10)
H350.48190.46550.43340.045*
C360.5362 (2)0.3956 (2)0.3673 (3)0.0288 (9)
H360.55380.43160.33240.035*
C410.6015 (2)0.2002 (2)0.2683 (2)0.0224 (8)
C420.5376 (2)0.1775 (2)0.2246 (3)0.0363 (10)
H420.50430.21260.20070.044*
C430.5220 (2)0.1044 (2)0.2156 (3)0.0425 (12)
H430.47810.08950.18540.051*
C440.5698 (2)0.0531 (2)0.2502 (3)0.0371 (10)
H440.55870.00280.24450.045*
C450.6337 (2)0.0747 (2)0.2931 (3)0.0348 (10)
H450.66680.03920.31640.042*
C460.6499 (2)0.1481 (2)0.3026 (3)0.0281 (9)
H460.69400.16280.33230.034*
Re20.234120 (8)0.330538 (8)0.174643 (9)0.01962 (4)
Br30.34651 (2)0.37327 (2)0.26052 (3)0.03643 (10)
Br40.30700 (2)0.27118 (2)0.07404 (3)0.03180 (9)
P20.12037 (5)0.30358 (5)0.08588 (6)0.01950 (19)
O30.22884 (14)0.42150 (13)0.10244 (16)0.0233 (6)
O40.21229 (15)0.26075 (15)0.23405 (16)0.0263 (6)
N30.18502 (17)0.41223 (17)0.24467 (19)0.0233 (7)
N40.17059 (18)0.47831 (17)0.20169 (19)0.0246 (7)
C50.19517 (19)0.4780 (2)0.1291 (2)0.0208 (7)
C60.1668 (2)0.4106 (2)0.3211 (3)0.0335 (10)
C70.1285 (3)0.4726 (3)0.3551 (3)0.0473 (13)
H7110.07970.45820.35920.071*
H7210.12880.51430.31660.071*
H7310.15200.48600.41170.071*
C80.1822 (3)0.3458 (3)0.3778 (3)0.0515 (14)
H8110.22860.32600.37010.077*
H8210.14590.30870.36290.077*
H8310.18220.36040.43740.077*
C510.1850 (2)0.5422 (2)0.0732 (2)0.0227 (8)
C520.1554 (2)0.6056 (2)0.1016 (3)0.0281 (9)
H520.14200.60760.15730.034*
C530.1455 (2)0.6653 (2)0.0489 (3)0.0318 (9)
H530.12590.70860.06870.038*
C540.1640 (2)0.6627 (2)−0.0328 (3)0.0337 (10)
H540.15650.7039−0.06920.040*
C550.1935 (2)0.6000 (2)−0.0616 (3)0.0357 (10)
H550.20640.5981−0.11760.043*
C560.2042 (2)0.5402 (2)−0.0087 (3)0.0284 (9)
H560.22480.4974−0.02830.034*
C610.1077 (2)0.3279 (2)−0.0267 (2)0.0229 (8)
C620.1628 (2)0.3508 (2)−0.0694 (2)0.0258 (8)
H620.20910.3548−0.03970.031*
C630.1504 (2)0.3678 (2)−0.1550 (2)0.0308 (9)
H630.18830.3834−0.18400.037*
C640.0835 (2)0.3623 (2)−0.1987 (2)0.0334 (10)
H640.07510.3746−0.25740.040*
C650.0284 (2)0.3389 (3)−0.1569 (3)0.0367 (10)
H65−0.01770.3345−0.18710.044*
C660.0404 (2)0.3218 (2)−0.0714 (3)0.0330 (9)
H660.00240.3058−0.04280.040*
C710.0498 (2)0.3505 (2)0.1299 (2)0.0241 (8)
C720.0273 (2)0.3236 (2)0.2048 (3)0.0346 (10)
H720.04580.27890.22810.042*
C73−0.0212 (3)0.3611 (3)0.2450 (3)0.0460 (12)
H73−0.03680.34210.29520.055*
C74−0.0471 (3)0.4268 (3)0.2117 (3)0.0491 (13)
H74−0.08060.45300.23920.059*
C75−0.0246 (3)0.4544 (3)0.1392 (3)0.0445 (12)
H75−0.04240.49980.11720.053*
C760.0236 (2)0.4168 (2)0.0980 (3)0.0323 (9)
H760.03890.43630.04780.039*
C810.0972 (2)0.2071 (2)0.0871 (2)0.0224 (8)
C820.1500 (2)0.1548 (2)0.0970 (2)0.0261 (8)
H820.19810.16930.10580.031*
C830.1329 (2)0.0814 (2)0.0944 (3)0.0309 (9)
H830.16940.04600.10100.037*
C840.0632 (2)0.0598 (2)0.0822 (3)0.0329 (10)
H840.05160.00960.08060.039*
C850.0101 (2)0.1115 (2)0.0723 (3)0.0354 (10)
H85−0.03790.09670.06370.043*
C860.0270 (2)0.1849 (2)0.0749 (3)0.0311 (9)
H86−0.00960.22020.06840.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.01965 (7)0.01528 (7)0.01927 (7)0.00080 (6)0.00211 (5)0.00075 (5)
Br10.0336 (2)0.0283 (2)0.02781 (19)0.00461 (17)0.00804 (16)−0.00207 (16)
Br20.0251 (2)0.0300 (2)0.0393 (2)−0.00504 (17)0.00004 (17)−0.00410 (18)
P10.0186 (5)0.0168 (4)0.0226 (4)0.0018 (4)0.0007 (4)0.0004 (4)
O10.0285 (14)0.0158 (12)0.0210 (12)0.0032 (11)0.0046 (11)0.0015 (10)
O20.0267 (14)0.0231 (14)0.0263 (14)0.0032 (11)0.0024 (11)0.0039 (11)
N10.0257 (17)0.0173 (15)0.0213 (15)0.0032 (13)0.0032 (13)−0.0004 (12)
N20.0287 (17)0.0183 (16)0.0248 (16)0.0028 (14)0.0014 (13)0.0013 (13)
C10.0172 (17)0.0178 (18)0.0246 (18)−0.0031 (14)−0.0002 (14)−0.0013 (14)
C20.033 (2)0.029 (2)0.0251 (19)0.0011 (18)0.0053 (17)−0.0027 (16)
C30.062 (3)0.045 (3)0.030 (2)0.016 (3)0.011 (2)−0.010 (2)
C40.083 (4)0.041 (3)0.026 (2)0.014 (3)0.012 (2)0.008 (2)
C110.0202 (18)0.0181 (18)0.0271 (19)0.0004 (15)0.0032 (15)0.0023 (15)
C120.031 (2)0.0198 (19)0.033 (2)−0.0027 (17)0.0050 (17)0.0001 (16)
C130.033 (2)0.019 (2)0.049 (3)0.0045 (17)0.009 (2)0.0052 (18)
C140.032 (2)0.032 (2)0.043 (2)0.0039 (19)0.0039 (19)0.018 (2)
C150.041 (3)0.035 (2)0.032 (2)0.002 (2)0.0011 (19)0.0102 (19)
C160.035 (2)0.024 (2)0.028 (2)0.0020 (17)0.0047 (17)0.0019 (16)
C210.029 (2)0.0169 (18)0.0239 (18)0.0008 (15)−0.0010 (15)0.0008 (14)
C220.034 (2)0.040 (3)0.034 (2)0.009 (2)−0.0013 (19)0.000 (2)
C230.050 (3)0.048 (3)0.039 (3)0.019 (3)−0.013 (2)0.003 (2)
C240.066 (4)0.033 (2)0.028 (2)0.000 (2)−0.011 (2)0.0034 (19)
C250.055 (3)0.040 (3)0.022 (2)−0.013 (2)0.001 (2)−0.0006 (18)
C260.031 (2)0.030 (2)0.027 (2)−0.0029 (18)0.0010 (16)−0.0032 (17)
C310.0187 (18)0.025 (2)0.0259 (19)0.0029 (16)0.0003 (15)−0.0008 (15)
C320.037 (2)0.030 (2)0.034 (2)0.0067 (19)0.0094 (19)0.0039 (18)
C330.044 (3)0.052 (3)0.035 (2)0.006 (2)0.015 (2)0.006 (2)
C340.038 (3)0.062 (3)0.030 (2)0.015 (2)0.010 (2)−0.007 (2)
C350.032 (2)0.037 (3)0.044 (3)0.010 (2)0.003 (2)−0.011 (2)
C360.024 (2)0.025 (2)0.037 (2)0.0036 (17)0.0036 (17)−0.0046 (17)
C410.0214 (19)0.0181 (18)0.0279 (19)0.0010 (15)0.0042 (15)−0.0020 (15)
C420.032 (2)0.025 (2)0.048 (3)0.0042 (19)−0.009 (2)−0.0017 (19)
C430.031 (2)0.030 (2)0.063 (3)−0.004 (2)−0.008 (2)−0.009 (2)
C440.039 (3)0.020 (2)0.052 (3)−0.0037 (19)0.002 (2)−0.0067 (19)
C450.032 (2)0.021 (2)0.050 (3)0.0038 (18)−0.003 (2)−0.0011 (19)
C460.026 (2)0.0202 (19)0.037 (2)−0.0003 (16)0.0000 (17)−0.0027 (17)
Re20.02176 (8)0.01789 (7)0.01966 (7)−0.00075 (6)0.00433 (5)0.00207 (5)
Br30.0303 (2)0.0309 (2)0.0458 (2)−0.00655 (18)−0.00375 (18)−0.00186 (19)
Br40.0334 (2)0.0324 (2)0.0322 (2)0.00594 (18)0.01408 (17)0.00429 (17)
P20.0210 (5)0.0188 (4)0.0194 (4)0.0006 (4)0.0053 (4)0.0011 (4)
O30.0292 (14)0.0176 (13)0.0243 (13)0.0014 (11)0.0077 (11)0.0033 (10)
O40.0303 (15)0.0265 (14)0.0219 (13)−0.0014 (12)0.0025 (11)0.0034 (11)
N30.0295 (17)0.0184 (16)0.0220 (15)−0.0019 (13)0.0039 (13)−0.0001 (12)
N40.0323 (18)0.0196 (16)0.0221 (15)0.0000 (14)0.0041 (13)0.0003 (13)
C50.0195 (18)0.0201 (18)0.0218 (17)−0.0039 (15)−0.0011 (14)−0.0022 (14)
C60.047 (3)0.033 (2)0.0221 (19)−0.002 (2)0.0112 (18)−0.0043 (17)
C70.067 (4)0.047 (3)0.033 (2)0.004 (3)0.025 (2)−0.007 (2)
C80.092 (4)0.044 (3)0.022 (2)0.006 (3)0.020 (2)0.006 (2)
C510.0203 (18)0.0203 (19)0.0267 (19)−0.0035 (15)0.0005 (15)0.0024 (15)
C520.027 (2)0.023 (2)0.034 (2)−0.0011 (17)0.0030 (17)−0.0008 (17)
C530.026 (2)0.020 (2)0.047 (3)0.0011 (17)−0.0019 (18)−0.0033 (18)
C540.032 (2)0.023 (2)0.043 (2)−0.0047 (18)−0.0029 (19)0.0092 (18)
C550.043 (3)0.033 (2)0.032 (2)−0.002 (2)0.009 (2)0.0068 (18)
C560.034 (2)0.022 (2)0.031 (2)−0.0009 (17)0.0071 (17)0.0054 (16)
C610.030 (2)0.0203 (18)0.0189 (17)0.0047 (16)0.0056 (15)0.0025 (14)
C620.031 (2)0.0233 (19)0.0238 (19)−0.0021 (17)0.0065 (16)−0.0019 (15)
C630.042 (2)0.029 (2)0.0227 (19)−0.0019 (19)0.0104 (18)−0.0005 (16)
C640.051 (3)0.033 (2)0.0165 (18)0.008 (2)0.0038 (18)−0.0013 (16)
C650.032 (2)0.050 (3)0.026 (2)0.006 (2)−0.0031 (17)−0.0018 (19)
C660.027 (2)0.044 (3)0.027 (2)0.0034 (19)0.0041 (17)0.0043 (18)
C710.0231 (19)0.0240 (19)0.0263 (19)−0.0009 (16)0.0074 (15)−0.0044 (15)
C720.035 (2)0.036 (2)0.035 (2)0.000 (2)0.0121 (19)0.0014 (19)
C730.037 (3)0.065 (4)0.039 (3)−0.002 (2)0.017 (2)−0.009 (2)
C740.035 (3)0.062 (4)0.052 (3)0.008 (2)0.014 (2)−0.025 (3)
C750.039 (3)0.034 (3)0.060 (3)0.014 (2)0.004 (2)−0.014 (2)
C760.033 (2)0.027 (2)0.037 (2)0.0004 (18)0.0050 (18)−0.0038 (18)
C810.029 (2)0.0206 (19)0.0178 (17)−0.0019 (16)0.0034 (15)−0.0007 (14)
C820.030 (2)0.024 (2)0.0255 (19)0.0008 (16)0.0079 (16)−0.0010 (15)
C830.041 (2)0.024 (2)0.029 (2)0.0032 (18)0.0068 (18)−0.0031 (16)
C840.049 (3)0.022 (2)0.026 (2)−0.0059 (19)−0.0021 (19)−0.0004 (16)
C850.032 (2)0.034 (2)0.037 (2)−0.0116 (19)−0.0091 (18)0.0049 (19)
C860.031 (2)0.026 (2)0.034 (2)−0.0006 (18)−0.0034 (18)0.0038 (17)
Geometric parameters (Å, º) top
Re1—O21.678 (3)Re2—O41.675 (3)
Re1—O12.027 (2)Re2—O32.021 (2)
Re1—N12.155 (3)Re2—N32.152 (3)
Re1—P12.4724 (10)Re2—P22.4810 (10)
Re1—Br12.4829 (4)Re2—Br42.4970 (4)
Re1—Br22.5252 (4)Re2—Br32.5147 (5)
P1—C211.816 (4)P2—C711.814 (4)
P1—C311.821 (4)P2—C611.821 (4)
P1—C411.821 (4)P2—C811.830 (4)
O1—C11.315 (4)O3—C51.320 (4)
N1—C21.303 (5)N3—C61.301 (5)
N1—N21.406 (4)N3—N41.402 (4)
N2—C11.294 (5)N4—C51.295 (5)
C1—C111.476 (5)C5—C511.473 (5)
C2—C41.489 (6)C6—C71.491 (6)
C2—C31.491 (6)C6—C81.496 (6)
C3—H3110.9800C7—H7110.9800
C3—H3210.9800C7—H7210.9800
C3—H3310.9800C7—H7310.9800
C4—H4110.9800C8—H8110.9800
C4—H4210.9800C8—H8210.9800
C4—H4310.9800C8—H8310.9800
C11—C121.391 (5)C51—C561.392 (5)
C11—C161.393 (5)C51—C521.395 (5)
C12—C131.385 (6)C52—C531.377 (6)
C12—H120.9500C52—H520.9500
C13—C141.378 (6)C53—C541.384 (6)
C13—H130.9500C53—H530.9500
C14—C151.381 (6)C54—C551.387 (6)
C14—H140.9500C54—H540.9500
C15—C161.382 (6)C55—C561.380 (6)
C15—H150.9500C55—H550.9500
C16—H160.9500C56—H560.9500
C21—C221.387 (6)C61—C621.387 (5)
C21—C261.393 (6)C61—C661.391 (6)
C22—C231.386 (6)C62—C631.380 (5)
C22—H220.9500C62—H620.9500
C23—C241.378 (7)C63—C641.377 (6)
C23—H230.9500C63—H630.9500
C24—C251.377 (7)C64—C651.382 (6)
C24—H240.9500C64—H640.9500
C25—C261.386 (6)C65—C661.378 (6)
C25—H250.9500C65—H650.9500
C26—H260.9500C66—H660.9500
C31—C361.393 (5)C71—C761.388 (6)
C31—C321.395 (6)C71—C721.401 (5)
C32—C331.388 (6)C72—C731.376 (6)
C32—H320.9500C72—H720.9500
C33—C341.376 (7)C73—C741.383 (8)
C33—H330.9500C73—H730.9500
C34—C351.383 (7)C74—C751.373 (7)
C34—H340.9500C74—H740.9500
C35—C361.378 (6)C75—C761.382 (6)
C35—H350.9500C75—H750.9500
C36—H360.9500C76—H760.9500
C41—C421.388 (6)C81—C821.389 (5)
C41—C461.392 (5)C81—C861.391 (6)
C42—C431.381 (6)C82—C831.387 (6)
C42—H420.9500C82—H820.9500
C43—C441.377 (6)C83—C841.381 (6)
C43—H430.9500C83—H830.9500
C44—C451.376 (6)C84—C851.384 (6)
C44—H440.9500C84—H840.9500
C45—C461.389 (6)C85—C861.388 (6)
C45—H450.9500C85—H850.9500
C46—H460.9500C86—H860.9500
O2—Re1—O1161.65 (12)O4—Re2—O3162.46 (12)
O2—Re1—N193.96 (12)O4—Re2—N395.14 (12)
O1—Re1—N173.84 (10)O3—Re2—N373.71 (11)
O2—Re1—P183.53 (10)O4—Re2—P284.30 (10)
O1—Re1—P183.83 (8)O3—Re2—P282.50 (8)
N1—Re1—P194.44 (9)N3—Re2—P291.27 (9)
O2—Re1—Br1104.18 (9)O4—Re2—Br4102.84 (9)
O1—Re1—Br189.52 (7)O3—Re2—Br489.61 (7)
N1—Re1—Br1161.31 (8)N3—Re2—Br4161.64 (8)
P1—Re1—Br192.08 (2)P2—Re2—Br494.15 (2)
O2—Re1—Br2101.66 (9)O4—Re2—Br3101.18 (9)
O1—Re1—Br290.71 (8)O3—Re2—Br391.34 (8)
N1—Re1—Br283.52 (9)N3—Re2—Br384.42 (9)
P1—Re1—Br2174.53 (2)P2—Re2—Br3173.29 (3)
Br1—Re1—Br288.359 (15)Br4—Re2—Br388.444 (16)
C21—P1—C31107.05 (18)C71—P2—C61104.28 (18)
C21—P1—C41105.04 (17)C71—P2—C81105.30 (18)
C31—P1—C41104.00 (17)C61—P2—C81104.29 (17)
C21—P1—Re1117.33 (13)C71—P2—Re2109.17 (13)
C31—P1—Re1107.98 (13)C61—P2—Re2120.00 (13)
C41—P1—Re1114.44 (13)C81—P2—Re2112.58 (13)
C1—O1—Re1117.1 (2)C5—O3—Re2117.5 (2)
C2—N1—N2114.5 (3)C6—N3—N4114.3 (3)
C2—N1—Re1130.3 (3)C6—N3—Re2130.4 (3)
N2—N1—Re1115.1 (2)N4—N3—Re2115.3 (2)
C1—N2—N1110.6 (3)C5—N4—N3110.8 (3)
N2—C1—O1123.0 (3)N4—C5—O3122.3 (3)
N2—C1—C11118.9 (3)N4—C5—C51119.6 (3)
O1—C1—C11118.0 (3)O3—C5—C51118.2 (3)
N1—C2—C4122.4 (4)N3—C6—C7121.3 (4)
N1—C2—C3120.8 (4)N3—C6—C8121.3 (4)
C4—C2—C3116.8 (4)C7—C6—C8117.5 (4)
C2—C3—H311109.5C6—C7—H711109.5
C2—C3—H321109.5C6—C7—H721109.5
H311—C3—H321109.5H711—C7—H721109.5
C2—C3—H331109.5C6—C7—H731109.5
H311—C3—H331109.5H711—C7—H731109.5
H321—C3—H331109.5H721—C7—H731109.5
C2—C4—H411109.5C6—C8—H811109.5
C2—C4—H421109.5C6—C8—H821109.5
H411—C4—H421109.5H811—C8—H821109.5
C2—C4—H431109.5C6—C8—H831109.5
H411—C4—H431109.5H811—C8—H831109.5
H421—C4—H431109.5H821—C8—H831109.5
C12—C11—C16119.5 (4)C56—C51—C52119.2 (4)
C12—C11—C1120.4 (3)C56—C51—C5120.4 (3)
C16—C11—C1120.0 (3)C52—C51—C5120.3 (3)
C13—C12—C11119.9 (4)C53—C52—C51120.1 (4)
C13—C12—H12120.0C53—C52—H52119.9
C11—C12—H12120.0C51—C52—H52119.9
C14—C13—C12120.1 (4)C52—C53—C54120.4 (4)
C14—C13—H13120.0C52—C53—H53119.8
C12—C13—H13120.0C54—C53—H53119.8
C13—C14—C15120.4 (4)C53—C54—C55119.9 (4)
C13—C14—H14119.8C53—C54—H54120.1
C15—C14—H14119.8C55—C54—H54120.1
C14—C15—C16120.0 (4)C56—C55—C54119.9 (4)
C14—C15—H15120.0C56—C55—H55120.0
C16—C15—H15120.0C54—C55—H55120.0
C15—C16—C11120.1 (4)C55—C56—C51120.4 (4)
C15—C16—H16120.0C55—C56—H56119.8
C11—C16—H16120.0C51—C56—H56119.8
C22—C21—C26119.1 (4)C62—C61—C66119.2 (4)
C22—C21—P1122.2 (3)C62—C61—P2122.5 (3)
C26—C21—P1118.6 (3)C66—C61—P2118.3 (3)
C23—C22—C21120.3 (4)C63—C62—C61120.1 (4)
C23—C22—H22119.8C63—C62—H62119.9
C21—C22—H22119.8C61—C62—H62119.9
C24—C23—C22120.1 (5)C64—C63—C62120.4 (4)
C24—C23—H23120.0C64—C63—H63119.8
C22—C23—H23120.0C62—C63—H63119.8
C25—C24—C23120.1 (4)C63—C64—C65120.0 (4)
C25—C24—H24119.9C63—C64—H64120.0
C23—C24—H24119.9C65—C64—H64120.0
C24—C25—C26120.2 (4)C66—C65—C64120.0 (4)
C24—C25—H25119.9C66—C65—H65120.0
C26—C25—H25119.9C64—C65—H65120.0
C25—C26—C21120.1 (4)C65—C66—C61120.4 (4)
C25—C26—H26119.9C65—C66—H66119.8
C21—C26—H26119.9C61—C66—H66119.8
C36—C31—C32119.0 (4)C76—C71—C72118.8 (4)
C36—C31—P1120.2 (3)C76—C71—P2121.9 (3)
C32—C31—P1120.5 (3)C72—C71—P2118.8 (3)
C33—C32—C31120.3 (4)C73—C72—C71120.8 (4)
C33—C32—H32119.8C73—C72—H72119.6
C31—C32—H32119.8C71—C72—H72119.6
C34—C33—C32119.9 (4)C72—C73—C74119.4 (5)
C34—C33—H33120.1C72—C73—H73120.3
C32—C33—H33120.1C74—C73—H73120.3
C33—C34—C35120.2 (4)C75—C74—C73120.4 (4)
C33—C34—H34119.9C75—C74—H74119.8
C35—C34—H34119.9C73—C74—H74119.8
C36—C35—C34120.2 (4)C74—C75—C76120.5 (5)
C36—C35—H35119.9C74—C75—H75119.7
C34—C35—H35119.9C76—C75—H75119.7
C35—C36—C31120.4 (4)C75—C76—C71120.0 (4)
C35—C36—H36119.8C75—C76—H76120.0
C31—C36—H36119.8C71—C76—H76120.0
C42—C41—C46119.0 (4)C82—C81—C86119.1 (4)
C42—C41—P1118.5 (3)C82—C81—P2119.9 (3)
C46—C41—P1122.4 (3)C86—C81—P2120.9 (3)
C43—C42—C41120.6 (4)C83—C82—C81120.4 (4)
C43—C42—H42119.7C83—C82—H82119.8
C41—C42—H42119.7C81—C82—H82119.8
C44—C43—C42120.2 (4)C84—C83—C82120.2 (4)
C44—C43—H43119.9C84—C83—H83119.9
C42—C43—H43119.9C82—C83—H83119.9
C45—C44—C43119.9 (4)C83—C84—C85119.9 (4)
C45—C44—H44120.0C83—C84—H84120.1
C43—C44—H44120.0C85—C84—H84120.1
C44—C45—C46120.3 (4)C84—C85—C86120.1 (4)
C44—C45—H45119.8C84—C85—H85120.0
C46—C45—H45119.8C86—C85—H85120.0
C45—C46—C41119.9 (4)C85—C86—C81120.4 (4)
C45—C46—H46120.0C85—C86—H86119.8
C41—C46—H46120.0C81—C86—H86119.8
O2—Re1—P1—C21−173.65 (17)O4—Re2—P2—C7185.74 (17)
O1—Re1—P1—C2119.68 (15)O3—Re2—P2—C71−82.68 (15)
N1—Re1—P1—C2192.87 (16)N3—Re2—P2—C71−9.29 (16)
Br1—Re1—P1—C21−69.61 (14)Br4—Re2—P2—C71−171.74 (14)
O2—Re1—P1—C3165.38 (16)O4—Re2—P2—C61−154.11 (17)
O1—Re1—P1—C31−101.29 (15)O3—Re2—P2—C6137.47 (16)
N1—Re1—P1—C31−28.11 (15)N3—Re2—P2—C61110.86 (16)
Br1—Re1—P1—C31169.42 (13)Br4—Re2—P2—C61−51.59 (14)
O2—Re1—P1—C41−49.88 (16)O4—Re2—P2—C81−30.82 (16)
O1—Re1—P1—C41143.44 (15)O3—Re2—P2—C81160.76 (14)
N1—Re1—P1—C41−143.37 (16)N3—Re2—P2—C81−125.85 (15)
Br1—Re1—P1—C4154.15 (13)Br4—Re2—P2—C8171.70 (13)
O2—Re1—O1—C145.1 (5)O4—Re2—O3—C546.6 (5)
N1—Re1—O1—C1−4.7 (2)N3—Re2—O3—C5−5.5 (3)
P1—Re1—O1—C191.7 (2)P2—Re2—O3—C588.1 (2)
Br1—Re1—O1—C1−176.1 (2)Br4—Re2—O3—C5−177.7 (2)
Br2—Re1—O1—C1−87.8 (2)Br3—Re2—O3—C5−89.3 (2)
O2—Re1—N1—C222.8 (4)O4—Re2—N3—C619.8 (4)
O1—Re1—N1—C2−171.2 (4)O3—Re2—N3—C6−174.0 (4)
P1—Re1—N1—C2106.6 (4)P2—Re2—N3—C6104.2 (4)
Br1—Re1—N1—C2−143.4 (3)Br4—Re2—N3—C6−148.5 (3)
Br2—Re1—N1—C2−78.5 (4)Br3—Re2—N3—C6−80.9 (4)
O2—Re1—N1—N2−161.3 (3)O4—Re2—N3—N4−160.7 (3)
O1—Re1—N1—N24.7 (2)O3—Re2—N3—N45.5 (2)
P1—Re1—N1—N2−77.5 (2)P2—Re2—N3—N4−76.3 (2)
Br1—Re1—N1—N232.5 (4)Br4—Re2—N3—N430.9 (5)
Br2—Re1—N1—N297.3 (2)Br3—Re2—N3—N498.5 (2)
C2—N1—N2—C1172.6 (3)C6—N3—N4—C5174.9 (4)
Re1—N1—N2—C1−4.0 (4)Re2—N3—N4—C5−4.7 (4)
N1—N2—C1—O1−0.1 (5)N3—N4—C5—O30.0 (5)
N1—N2—C1—C11177.7 (3)N3—N4—C5—C51179.4 (3)
Re1—O1—C1—N24.5 (5)Re2—O3—C5—N45.1 (5)
Re1—O1—C1—C11−173.4 (2)Re2—O3—C5—C51−174.3 (2)
N2—N1—C2—C4−178.6 (4)N4—N3—C6—C74.8 (6)
Re1—N1—C2—C4−2.6 (6)Re2—N3—C6—C7−175.8 (3)
N2—N1—C2—C31.7 (6)N4—N3—C6—C8−176.4 (4)
Re1—N1—C2—C3177.6 (3)Re2—N3—C6—C83.0 (7)
N2—C1—C11—C1214.6 (5)N4—C5—C51—C56−173.1 (4)
O1—C1—C11—C12−167.5 (3)O3—C5—C51—C566.3 (5)
N2—C1—C11—C16−163.4 (4)N4—C5—C51—C526.3 (6)
O1—C1—C11—C1614.6 (5)O3—C5—C51—C52−174.3 (3)
C16—C11—C12—C130.4 (6)C56—C51—C52—C53−0.1 (6)
C1—C11—C12—C13−177.6 (4)C5—C51—C52—C53−179.5 (4)
C11—C12—C13—C14−0.4 (6)C51—C52—C53—C540.8 (6)
C12—C13—C14—C150.3 (7)C52—C53—C54—C55−0.8 (7)
C13—C14—C15—C16−0.2 (7)C53—C54—C55—C560.2 (7)
C14—C15—C16—C110.2 (7)C54—C55—C56—C510.5 (7)
C12—C11—C16—C15−0.3 (6)C52—C51—C56—C55−0.5 (6)
C1—C11—C16—C15177.7 (4)C5—C51—C56—C55178.9 (4)
C31—P1—C21—C22−13.9 (4)C71—P2—C61—C62133.1 (3)
C41—P1—C21—C2296.2 (4)C81—P2—C61—C62−116.6 (3)
Re1—P1—C21—C22−135.4 (3)Re2—P2—C61—C6210.6 (4)
C31—P1—C21—C26168.8 (3)C71—P2—C61—C66−48.2 (4)
C41—P1—C21—C26−81.1 (3)C81—P2—C61—C6662.0 (4)
Re1—P1—C21—C2647.3 (3)Re2—P2—C61—C66−170.8 (3)
C26—C21—C22—C23−1.5 (7)C66—C61—C62—C630.6 (6)
P1—C21—C22—C23−178.7 (4)P2—C61—C62—C63179.2 (3)
C21—C22—C23—C240.4 (8)C61—C62—C63—C640.0 (6)
C22—C23—C24—C250.9 (8)C62—C63—C64—C65−0.7 (6)
C23—C24—C25—C26−1.2 (7)C63—C64—C65—C660.7 (7)
C24—C25—C26—C210.1 (7)C64—C65—C66—C610.0 (7)
C22—C21—C26—C251.2 (6)C62—C61—C66—C65−0.6 (6)
P1—C21—C26—C25178.5 (3)P2—C61—C66—C65−179.3 (3)
C21—P1—C31—C36−52.4 (4)C61—P2—C71—C76−31.9 (4)
C41—P1—C31—C36−163.3 (3)C81—P2—C71—C76−141.4 (3)
Re1—P1—C31—C3674.7 (3)Re2—P2—C71—C7697.5 (3)
C21—P1—C31—C32134.6 (3)C61—P2—C71—C72156.3 (3)
C41—P1—C31—C3223.7 (4)C81—P2—C71—C7246.8 (4)
Re1—P1—C31—C32−98.3 (3)Re2—P2—C71—C72−74.3 (3)
C36—C31—C32—C330.0 (6)C76—C71—C72—C731.7 (7)
P1—C31—C32—C33173.1 (4)P2—C71—C72—C73173.7 (4)
C31—C32—C33—C340.8 (7)C71—C72—C73—C74−1.1 (7)
C32—C33—C34—C35−0.9 (8)C72—C73—C74—C750.0 (8)
C33—C34—C35—C360.0 (7)C73—C74—C75—C760.6 (8)
C34—C35—C36—C310.8 (7)C74—C75—C76—C710.0 (7)
C32—C31—C36—C35−0.8 (6)C72—C71—C76—C75−1.1 (6)
P1—C31—C36—C35−173.9 (3)P2—C71—C76—C75−172.9 (4)
C21—P1—C41—C42−45.5 (4)C71—P2—C81—C82−149.4 (3)
C31—P1—C41—C4266.8 (4)C61—P2—C81—C82101.1 (3)
Re1—P1—C41—C42−175.6 (3)Re2—P2—C81—C82−30.6 (3)
C21—P1—C41—C46138.9 (3)C71—P2—C81—C8633.0 (4)
C31—P1—C41—C46−108.8 (3)C61—P2—C81—C86−76.5 (3)
Re1—P1—C41—C468.8 (4)Re2—P2—C81—C86151.8 (3)
C46—C41—C42—C430.4 (7)C86—C81—C82—C830.4 (6)
P1—C41—C42—C43−175.3 (4)P2—C81—C82—C83−177.2 (3)
C41—C42—C43—C440.2 (8)C81—C82—C83—C84−0.3 (6)
C42—C43—C44—C45−0.7 (8)C82—C83—C84—C850.2 (6)
C43—C44—C45—C460.8 (7)C83—C84—C85—C86−0.2 (6)
C44—C45—C46—C41−0.2 (7)C84—C85—C86—C810.3 (6)
C42—C41—C46—C45−0.4 (6)C82—C81—C86—C85−0.4 (6)
P1—C41—C46—C45175.2 (3)P2—C81—C86—C85177.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···Br30.952.943.819 (5)154
C85—H85···Br2i0.952.923.587 (4)128
Symmetry code: (i) x−1, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula[ReBr2(C10H11N2O)O(C18H15P)]
Mr799.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)19.1130 (5), 18.3910 (4), 15.8140 (4)
β (°) 97.410 (1)
V (Å3)5512.3 (2)
Z8
Radiation typeMo Kα
µ (mm−1)7.40
Crystal size (mm)0.39 × 0.35 × 0.16
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.589, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		50272, 13695, 11062
Rint0.031
(sin θ/λ)max (Å−1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.066, 1.11
No. of reflections13695
No. of parameters649
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0171P)2 + 13.1603P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å−3)1.11, −1.33

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SIR97 (Altomare et al., 1999), ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···Br30.952.943.819 (5)153.6
C85—H85···Br2i0.952.923.587 (4)127.8
Symmetry code: (i) x−1, −y+1/2, z−1/2.
 

Acknowledgements

The authors thank Mrs Rose van der Vyver for helpful discussions and a lifetime of joy.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.  Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationEtter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGerber, T. I. A., Betz, R., Booysen, I. N., Potgieter, K. C. & Mayer, P. (2011). Polyhedron, 30, 1739–1745.  Web of Science CSD CrossRef CAS Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationPotgieter, K. C., Gerber, T. I. A. & Mayer, P. (2010). Polyhedron, 29, 1423–1430.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page m1337
https://doi.org/10.1107/S1600536811035811
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