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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m773.
Published online 2008 May 3. doi:  10.1107/S1600536808010684
PMCID: PMC2961474

(2-Hydroxy­phenyl­imido-κN)(methano­lato-κO)[2-(2-oxidobenzyl­ideneamino)phenolato-κ2 O,N,O′](triphenyl­phosphine-κP)rhenium(V)

Abstract

In the neutral title compound, [Re(C6H5NO)(C13H9NO2)(CH3O)(C18H15P)], an 18-valence-electron complex, the ReV ion lies in an octa­hedral coordination geometry with the tridentate dianionic Schiff base 2-(2-oxidobenzyl­idene­amino)phenolate ligand occupying three equatorial coordination sites, and with the triphenyl­phosphine ligand situated trans to the imine N atom. The ReV coordination is completed with a methano­late ligand and a 2-hydroxy­phenyl­imido(2-) ligand. There are two molecules in the asymmetric unit. The crystal structure involves O—H(...)O and C—H(...)O hydrogen bonds. One N and one C atom are disordered over two positions; the site occupancy factors are ca 0.7 and 0.3.

Related literature

For related literature, see: Chen et al. (2000 [triangle], 2001 [triangle]); Femia et al. (2001 [triangle]); Sheldrick (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m773-scheme1.jpg

Experimental

Crystal data

  • [Re(C6H5NO)(C13H9NO2)(CH3O)(C18H15P)]
  • M r = 797.86
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m773-efi1.jpg
  • a = 10.0193 (2) Å
  • b = 32.9759 (3) Å
  • c = 19.4605 (2) Å
  • β = 90.1597 (4)°
  • V = 6429.64 (16) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.87 mm−1
  • T = 150 K
  • 0.24 × 0.24 × 0.06 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 [triangle]) T min = 0.39, T max = 0.79
  • 56004 measured reflections
  • 14195 independent reflections
  • 10958 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.085
  • S = 0.99
  • 13952 reflections
  • 847 parameters
  • 614 restraints
  • H-atom parameters constrained
  • Δρmax = 2.85 e Å−3
  • Δρmin = −3.36 e Å−3

Data collection: COLLECT (Nonius, 2001 [triangle]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 [triangle]); molecular graphics: CAMERON (Watkin et al., 1996 [triangle]); software used to prepare material for publication: CRYSTALS.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010684/br2071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010684/br2071Isup2.hkl

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

Acknowledgments

JPH thanks Merton College and the EPSRC for financial support. PJB thanks GlaxoSmithKlein for a postdoctoral fellowship.

supplementary crystallographic information

Comment

The asymmetric unit contains two crystallographically distinct molecules, neither of which possess any crystallographic symmetry. These differ in the conformation of the PPh3 ligands. One of the molecules (Re2 etc.) exhibited unusually large thermal parameters for some of the atoms of the imine ligand, suggesting that it may be disordered. This was modelled satisfactorily by 'splitting' the nitrogen and one carbon atom. The hydroxyl groups of the coordinated 2-hydroxyphenylimido(2-) ligands form intramolecular hydrogen bonds to an oxygen atom of the imido ligand (O3···O1, 2.694 (6) Å and O7···O5, 2.720 (6) Å).

Experimental

Dark-brown crystals of the neutral ReV complex were isolated as a by-product from the crude reaction mixture after reacting [ReIIICl3(CH3CN)(PPh3)2] (0.40 g, 5.0 x 10 -4 mol) with 3 equiv. of the Schiff base salicylaldehyde-2-hydroxyaniline (0.32 g, 1.5 x 10 -3 mol) in the presence of excess triethylamine, in methanol (30 ml). After stirring under reflux for 8 h, the reaction mixture was allowed to cool for 12 h during which time crystals formed.

Refinement

The structure contains two independent molecules in the asymmetric unit (Z'=2). On of them is well resolved except for a marginal Hirshfeld test on atoms C7—C8. In the other molecule, the [salicylaldehyde-2-hydroxyanilato(2-)] moiety is disordered with the atoms N103 and N203, and C145 and C245 being clearly distinguished in a difference map. Refinement of the disorder was achieved by the use of Marquardt shift limiting restraints (damping) and molecular geometry and thermal simlarity restraints.

The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints.

Figures

Fig. 1.
ORTEP representation of the title complex with displacement ellipsoids at 50% probability. H atoms have been omitted for clarity.
Fig. 2.
ORTEP representation (50% probability) of the two crystallographically distinct molecules in the asymmetric unit.

Crystal data

[Re(C6H5NO)(C13H9NO2)(CH3O)(C18H15P)]F000 = 3168
Mr = 797.86Dx = 1.648 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 56004 reflections
a = 10.0193 (2) Åθ = 5–28º
b = 32.9759 (3) ŵ = 3.87 mm1
c = 19.4605 (2) ÅT = 150 K
β = 90.1597 (4)ºPlate, dark brown
V = 6429.64 (16) Å30.24 × 0.24 × 0.06 mm
Z = 8

Data collection

Area diffractometer10958 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.052
T = 150 Kθmax = 27.6º
ω scansθmin = 5.2º
Absorption correction: multi-scan(DENZO/SCALEPACK; Otwinowski & Minor, 1997)h = −12→12
Tmin = 0.39, Tmax = 0.79k = −42→42
56004 measured reflectionsl = −25→25
14195 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.085  Method = Modified Sheldrick (2008) w = 1/[σ2(F2) + (0.01P)2 + 33.25P], where P = [max(Fo2,0) + 2Fc2]/3
S = 0.99(Δ/σ)max = 0.002
13952 reflectionsΔρmax = 2.85 e Å3
847 parametersΔρmin = −3.36 e Å3
614 restraintsExtinction correction: None

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Re10.335488 (19)0.426935 (7)0.267904 (10)0.0258
O10.4009 (3)0.45761 (11)0.35638 (18)0.0311
C10.5212 (5)0.44409 (16)0.3784 (2)0.0256
C20.5808 (5)0.46241 (18)0.4355 (3)0.0354
C30.7041 (6)0.4494 (2)0.4585 (3)0.0428
C40.7718 (6)0.4188 (2)0.4258 (3)0.0450
C50.7142 (5)0.40022 (18)0.3692 (3)0.0390
C60.5893 (5)0.41223 (17)0.3462 (3)0.0295
N10.5143 (4)0.39498 (14)0.2899 (2)0.0353
C70.5504 (6)0.36392 (18)0.2578 (3)0.0394
C80.4841 (5)0.34664 (17)0.1976 (3)0.0321
C90.5415 (6)0.31020 (18)0.1743 (3)0.0401
C100.4927 (6)0.2899 (2)0.1185 (3)0.0464
C110.3827 (7)0.3060 (2)0.0845 (3)0.0476
C120.3247 (6)0.34162 (19)0.1052 (3)0.0378
C130.3724 (5)0.36310 (17)0.1623 (3)0.0332
O20.3101 (4)0.39741 (12)0.17743 (17)0.0350
N20.2287 (4)0.39752 (13)0.3194 (2)0.0242
C140.1583 (5)0.37914 (16)0.3718 (2)0.0251
C150.0806 (5)0.34454 (16)0.3589 (3)0.0311
C160.0163 (5)0.32490 (18)0.4116 (3)0.0378
C170.0291 (5)0.33928 (18)0.4783 (3)0.0363
C180.1056 (5)0.37316 (17)0.4923 (3)0.0324
C190.1705 (5)0.39350 (16)0.4391 (2)0.0255
O30.2464 (3)0.42580 (11)0.45571 (17)0.0316
O40.4528 (3)0.46395 (12)0.2215 (2)0.0390
C200.5704 (6)0.4654 (3)0.1904 (4)0.0755
P10.14834 (12)0.46856 (4)0.23254 (6)0.0235
C210.0321 (5)0.43868 (16)0.1788 (3)0.0265
C22−0.0394 (5)0.40837 (19)0.2099 (3)0.0389
C23−0.1214 (6)0.3834 (2)0.1718 (3)0.0459
C24−0.1324 (7)0.3893 (2)0.1015 (4)0.0552
C25−0.0620 (7)0.4197 (2)0.0704 (3)0.0566
C260.0197 (6)0.44445 (19)0.1090 (3)0.0393
C270.1911 (5)0.51265 (16)0.1801 (2)0.0252
C280.2798 (5)0.50819 (18)0.1253 (2)0.0313
C290.3110 (6)0.54079 (19)0.0842 (3)0.0392
C300.2544 (6)0.57833 (19)0.0968 (3)0.0418
C310.1678 (6)0.58301 (18)0.1505 (3)0.0405
C320.1367 (5)0.55041 (17)0.1929 (3)0.0331
C330.0393 (5)0.48936 (15)0.2985 (2)0.0239
C340.0928 (5)0.50044 (16)0.3615 (2)0.0274
C350.0119 (5)0.51914 (16)0.4101 (3)0.0290
C36−0.1211 (5)0.52736 (17)0.3962 (3)0.0352
C37−0.1735 (5)0.51677 (18)0.3336 (3)0.0389
C38−0.0951 (5)0.49755 (18)0.2851 (3)0.0343
Re20.65712 (2)0.188938 (7)0.281907 (11)0.0288
O50.7172 (3)0.23421 (11)0.35005 (19)0.0353
C390.6234 (5)0.26209 (16)0.3650 (3)0.0270
C400.6492 (6)0.29110 (18)0.4152 (3)0.0360
C410.5526 (7)0.31904 (18)0.4336 (3)0.0496
C420.4290 (7)0.3181 (2)0.4027 (3)0.0544
C430.4026 (6)0.2901 (2)0.3520 (3)0.0497
C440.4983 (5)0.26254 (16)0.3323 (2)0.0301
N1030.4943 (5)0.22937 (17)0.2813 (3)0.02790.7292
C1450.3975 (7)0.2261 (2)0.2390 (3)0.03160.7292
C460.3818 (5)0.19131 (16)0.1954 (3)0.0307
C470.2645 (6)0.1960 (2)0.1550 (3)0.0537
C480.2186 (7)0.1650 (3)0.1142 (3)0.0669
C490.2873 (7)0.1293 (3)0.1119 (3)0.0598
C500.3991 (6)0.12388 (19)0.1494 (3)0.0389
C510.4511 (5)0.15396 (17)0.1918 (3)0.0300
O60.5628 (3)0.14568 (11)0.22653 (19)0.0342
N40.7487 (4)0.21231 (13)0.2162 (2)0.0290
C520.8353 (5)0.23423 (16)0.1770 (3)0.0268
C530.8459 (5)0.22802 (17)0.1053 (3)0.0338
C540.9336 (6)0.25030 (18)0.0662 (3)0.0376
C551.0136 (6)0.27876 (19)0.0977 (3)0.0430
C561.0058 (6)0.28569 (19)0.1671 (3)0.0411
C570.9162 (5)0.26396 (17)0.2072 (3)0.0328
O70.9078 (4)0.27265 (13)0.27508 (19)0.0496
O80.5679 (3)0.16633 (11)0.36129 (18)0.0346
C580.5740 (6)0.1690 (2)0.4332 (3)0.0454
P20.84347 (12)0.14393 (4)0.30527 (6)0.0237
C590.9067 (5)0.11364 (16)0.2334 (2)0.0245
C600.8667 (5)0.12224 (17)0.1664 (3)0.0309
C610.9140 (6)0.09914 (18)0.1123 (3)0.0351
C620.9999 (6)0.06725 (19)0.1250 (3)0.0411
C631.0381 (5)0.05808 (18)0.1910 (3)0.0390
C640.9927 (5)0.08123 (17)0.2453 (3)0.0309
C650.8028 (5)0.10430 (16)0.3673 (2)0.0270
C660.7012 (5)0.07760 (18)0.3496 (3)0.0353
C670.6680 (6)0.04605 (18)0.3925 (3)0.0396
C680.7342 (6)0.0408 (2)0.4543 (3)0.0434
C690.8325 (6)0.0677 (2)0.4733 (3)0.0488
C700.8689 (5)0.0992 (2)0.4296 (3)0.0396
C710.9885 (5)0.16904 (16)0.3422 (2)0.0262
C720.9667 (5)0.19405 (19)0.3990 (3)0.0372
C731.0719 (6)0.2129 (2)0.4330 (3)0.0434
C741.2007 (6)0.20680 (19)0.4107 (3)0.0421
C751.2234 (6)0.18277 (18)0.3542 (3)0.0389
C761.1182 (5)0.16410 (16)0.3200 (3)0.0293
H310.27290.43900.42320.0514*
H710.84820.26090.29690.0742*
H210.53610.48350.45810.0421*
H24520.74220.46170.49790.0513*
H410.85580.41080.44130.0530*
H510.75820.37980.34620.0462*
H24530.62620.34990.27420.0481*
H910.61560.29960.19810.0502*
H1010.53160.26600.10360.0590*
H1110.34730.29220.04700.0569*
H1210.25130.35190.08070.0441*
H1510.07130.33440.31400.0389*
H161−0.03350.30200.40200.0459*
H171−0.01630.32580.51380.0437*
H1810.11450.38270.53690.0393*
H2010.58260.49200.17120.1122*
H2030.64140.46010.22210.1121*
H2020.57350.44570.15410.1123*
H221−0.03250.40450.25770.0491*
H231−0.16840.36250.19350.0549*
H241−0.18800.37270.07510.0649*
H251−0.06920.42410.02270.0711*
H2610.06500.46520.08690.0453*
H2810.31800.48260.11700.0376*
H2910.36790.53790.04700.0482*
H3010.27560.60000.06810.0522*
H3110.12930.60820.15790.0514*
H3210.07960.55390.23060.0399*
H3410.18330.49560.37100.0337*
H3510.04680.52640.45260.0330*
H361−0.17520.53960.42930.0436*
H371−0.26080.52230.32400.0449*
H381−0.13220.49020.24280.0404*
H4010.73350.29190.43680.0421*
H4110.57310.33830.46670.0648*
H4210.36430.33610.41650.0589*
H4310.31960.28980.33100.0620*
H4710.21760.22020.15570.0651*
H4810.13990.16880.08850.0800*
H4910.25790.10810.08350.0719*
H5010.44570.09930.14780.0450*
H5310.79260.20840.08450.0392*
H5410.93590.24650.01800.0459*
H5511.07480.29370.07190.0517*
H5611.06160.30510.18690.0487*
H5820.48680.16310.45140.0674*
H5810.60120.19600.44790.0674*
H5830.63770.14940.45130.0672*
H6010.80800.14380.15840.0379*
H6110.88780.10540.06790.0419*
H6211.03120.05180.08830.0500*
H6311.09490.03630.19870.0452*
H6411.01900.07470.29030.0345*
H6610.65520.08110.30790.0415*
H6710.60110.02780.37990.0469*
H6810.71190.01920.48260.0540*
H6910.87390.06450.51560.0578*
H7010.93770.11650.44240.0458*
H7210.88090.19860.41470.0439*
H7311.05350.22950.47030.0488*
H7411.27250.21860.43430.0527*
H7511.31010.17880.33860.0487*
H7611.13690.14760.28210.0347*
N2030.4631 (14)0.2133 (4)0.2461 (7)0.02870.2708
C2450.4222 (16)0.2442 (5)0.2775 (7)0.02890.2708
H14510.33340.24720.23590.0398*0.7292
H24510.33850.25550.26470.0398*0.2708

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Re10.02088 (10)0.03125 (12)0.02539 (11)0.00382 (9)0.00238 (8)0.00394 (9)
O10.0259 (18)0.030 (2)0.037 (2)−0.0006 (15)−0.0077 (15)0.0008 (16)
C10.020 (2)0.030 (3)0.027 (3)−0.004 (2)−0.0071 (19)0.007 (2)
C20.037 (3)0.038 (3)0.031 (3)−0.006 (2)0.000 (2)−0.004 (2)
C30.038 (3)0.061 (4)0.029 (3)−0.015 (3)−0.011 (2)0.007 (3)
C40.029 (3)0.051 (4)0.054 (4)−0.001 (2)−0.007 (2)0.016 (3)
C50.032 (3)0.037 (3)0.048 (3)0.006 (2)0.003 (2)0.008 (2)
C60.028 (3)0.032 (3)0.029 (3)−0.006 (2)−0.002 (2)0.004 (2)
N10.035 (2)0.036 (3)0.035 (2)0.003 (2)0.0063 (19)0.005 (2)
C70.043 (3)0.036 (3)0.040 (3)0.005 (2)0.013 (2)0.006 (2)
C80.036 (3)0.034 (3)0.027 (3)−0.005 (2)0.003 (2)−0.001 (2)
C90.045 (3)0.039 (3)0.036 (3)0.005 (2)0.008 (2)0.007 (2)
C100.060 (4)0.042 (4)0.036 (3)0.013 (3)0.012 (3)−0.003 (2)
C110.061 (4)0.052 (4)0.030 (3)−0.001 (3)0.005 (3)−0.012 (3)
C120.037 (3)0.051 (4)0.025 (3)0.003 (2)0.004 (2)0.002 (2)
C130.041 (3)0.031 (3)0.028 (3)0.001 (2)0.013 (2)0.001 (2)
O20.039 (2)0.040 (2)0.0260 (19)0.0152 (17)0.0013 (15)−0.0028 (16)
N20.019 (2)0.030 (2)0.024 (2)0.0037 (17)−0.0035 (16)−0.0042 (17)
C140.021 (2)0.029 (3)0.025 (2)0.002 (2)0.0053 (19)0.000 (2)
C150.028 (3)0.032 (3)0.034 (3)−0.001 (2)0.005 (2)−0.003 (2)
C160.029 (3)0.037 (3)0.047 (3)−0.007 (2)0.007 (2)0.000 (2)
C170.035 (3)0.035 (3)0.039 (3)0.002 (2)0.009 (2)0.006 (2)
C180.033 (3)0.038 (3)0.026 (3)0.003 (2)0.005 (2)−0.003 (2)
C190.022 (2)0.027 (3)0.027 (3)0.002 (2)0.0003 (19)0.002 (2)
O30.0334 (19)0.036 (2)0.0252 (18)−0.0073 (16)0.0014 (15)−0.0004 (16)
O40.0212 (18)0.047 (2)0.049 (2)0.0023 (16)0.0080 (16)0.0198 (18)
C200.036 (3)0.093 (5)0.098 (5)0.011 (3)0.013 (3)0.042 (3)
P10.0205 (6)0.0314 (8)0.0185 (6)0.0014 (5)−0.0006 (5)−0.0006 (6)
C210.020 (2)0.033 (3)0.026 (3)0.004 (2)−0.0038 (19)−0.008 (2)
C220.028 (3)0.049 (4)0.040 (3)0.000 (2)−0.009 (2)0.003 (2)
C230.039 (3)0.042 (4)0.058 (4)−0.009 (2)0.004 (3)−0.004 (3)
C240.050 (4)0.058 (4)0.058 (4)−0.015 (3)−0.015 (3)−0.021 (3)
C250.067 (4)0.071 (5)0.032 (3)−0.013 (3)−0.012 (3)−0.013 (3)
C260.045 (3)0.044 (3)0.029 (3)−0.007 (2)−0.007 (2)−0.003 (2)
C270.023 (2)0.030 (3)0.022 (2)0.001 (2)−0.0038 (19)0.001 (2)
C280.028 (3)0.044 (3)0.022 (2)−0.001 (2)−0.006 (2)0.000 (2)
C290.040 (3)0.052 (4)0.025 (3)−0.013 (3)−0.001 (2)0.001 (2)
C300.050 (3)0.037 (3)0.038 (3)−0.011 (3)−0.008 (2)0.011 (2)
C310.043 (3)0.027 (3)0.052 (3)−0.001 (2)−0.004 (3)0.005 (2)
C320.031 (3)0.034 (3)0.034 (3)0.000 (2)0.001 (2)−0.002 (2)
C330.024 (2)0.027 (3)0.021 (2)0.0042 (19)0.0030 (19)0.0036 (19)
C340.028 (3)0.032 (3)0.022 (2)0.001 (2)−0.002 (2)0.001 (2)
C350.037 (3)0.030 (3)0.021 (2)−0.001 (2)−0.002 (2)−0.005 (2)
C360.040 (3)0.036 (3)0.030 (3)0.004 (2)0.011 (2)−0.003 (2)
C370.027 (3)0.046 (4)0.044 (3)0.007 (2)0.009 (2)−0.002 (2)
C380.029 (3)0.047 (3)0.027 (3)0.004 (2)−0.002 (2)−0.002 (2)
Re20.02128 (11)0.03115 (13)0.03394 (12)0.00348 (9)0.00380 (8)0.00742 (10)
O50.0309 (19)0.036 (2)0.040 (2)0.0039 (16)0.0085 (16)0.0016 (17)
C390.026 (3)0.029 (3)0.026 (3)−0.002 (2)0.005 (2)−0.002 (2)
C400.037 (3)0.041 (3)0.030 (3)−0.013 (2)0.001 (2)−0.002 (2)
C410.085 (4)0.029 (3)0.036 (3)−0.011 (3)0.016 (3)−0.010 (2)
C420.060 (4)0.050 (4)0.054 (4)0.030 (3)0.019 (3)0.015 (3)
C430.041 (3)0.065 (4)0.043 (3)0.014 (3)0.001 (2)0.021 (3)
C440.033 (2)0.030 (2)0.027 (2)−0.0051 (19)−0.0010 (18)0.0018 (18)
N1030.027 (2)0.026 (3)0.031 (2)0.0012 (19)0.0012 (19)0.0043 (19)
C1450.032 (3)0.029 (3)0.034 (3)0.003 (2)−0.002 (2)0.001 (2)
C460.032 (2)0.030 (2)0.030 (2)−0.0026 (19)−0.0023 (18)0.0005 (18)
C470.041 (3)0.069 (4)0.051 (4)0.022 (3)0.008 (3)0.024 (3)
C480.036 (3)0.127 (6)0.038 (3)−0.022 (3)−0.020 (3)0.010 (3)
C490.061 (4)0.089 (5)0.029 (3)−0.041 (3)0.003 (3)−0.011 (3)
C500.046 (3)0.040 (3)0.031 (3)−0.008 (2)0.009 (2)−0.008 (2)
C510.025 (3)0.039 (3)0.026 (3)−0.005 (2)0.000 (2)0.004 (2)
O60.0297 (19)0.030 (2)0.043 (2)−0.0045 (15)−0.0053 (16)0.0109 (16)
N40.025 (2)0.032 (3)0.030 (2)0.0013 (18)0.0009 (17)0.0028 (18)
C520.027 (3)0.024 (3)0.030 (3)0.005 (2)−0.001 (2)0.005 (2)
C530.035 (3)0.032 (3)0.034 (3)−0.002 (2)−0.004 (2)0.001 (2)
C540.043 (3)0.043 (3)0.028 (3)0.004 (2)0.007 (2)0.008 (2)
C550.044 (3)0.047 (4)0.038 (3)−0.004 (3)0.012 (2)0.011 (2)
C560.037 (3)0.040 (3)0.047 (3)−0.011 (2)0.005 (2)0.002 (2)
C570.036 (3)0.031 (3)0.031 (3)−0.003 (2)0.009 (2)−0.002 (2)
O70.056 (3)0.057 (3)0.036 (2)−0.027 (2)0.0111 (18)−0.0117 (19)
O80.0298 (19)0.037 (2)0.037 (2)0.0049 (16)0.0123 (15)0.0092 (16)
C580.043 (3)0.058 (4)0.036 (3)0.012 (3)0.012 (2)0.005 (3)
P20.0213 (6)0.0301 (8)0.0197 (6)0.0015 (5)−0.0002 (5)−0.0002 (5)
C590.022 (2)0.029 (3)0.023 (2)0.000 (2)0.0010 (19)−0.003 (2)
C600.030 (3)0.036 (3)0.026 (3)−0.005 (2)−0.001 (2)−0.001 (2)
C610.042 (3)0.046 (3)0.018 (2)−0.009 (2)0.002 (2)−0.005 (2)
C620.038 (3)0.047 (4)0.038 (3)−0.014 (2)0.012 (2)−0.019 (2)
C630.029 (3)0.036 (3)0.052 (3)0.005 (2)0.002 (2)−0.012 (2)
C640.027 (3)0.037 (3)0.029 (3)0.003 (2)−0.003 (2)−0.001 (2)
C650.024 (2)0.033 (3)0.024 (2)0.002 (2)−0.0009 (19)0.000 (2)
C660.035 (3)0.041 (3)0.030 (3)0.001 (2)−0.003 (2)0.007 (2)
C670.045 (3)0.038 (3)0.036 (3)−0.009 (2)0.001 (2)0.005 (2)
C680.050 (3)0.047 (4)0.034 (3)0.002 (3)0.002 (2)0.016 (2)
C690.038 (3)0.076 (4)0.032 (3)−0.005 (3)−0.002 (2)0.017 (3)
C700.030 (3)0.055 (4)0.033 (3)−0.002 (2)−0.006 (2)0.009 (2)
C710.030 (3)0.026 (3)0.022 (2)−0.001 (2)−0.0020 (19)0.002 (2)
C720.029 (3)0.054 (4)0.028 (3)−0.002 (2)−0.002 (2)−0.010 (2)
C730.044 (3)0.054 (4)0.032 (3)−0.002 (3)−0.005 (2)−0.016 (2)
C740.039 (3)0.045 (4)0.042 (3)−0.012 (2)−0.007 (2)0.001 (3)
C750.030 (3)0.039 (3)0.048 (3)−0.008 (2)0.006 (2)0.004 (2)
C760.027 (3)0.030 (3)0.031 (3)−0.004 (2)0.006 (2)0.001 (2)
N2030.029 (3)0.028 (4)0.029 (3)0.001 (3)−0.001 (3)0.002 (3)
C2450.031 (4)0.029 (4)0.027 (3)−0.002 (3)−0.002 (3)0.001 (3)

Geometric parameters (Å, °)

Re1—O12.100 (3)Re2—O52.084 (4)
Re1—N12.122 (5)Re2—N1032.107 (6)
Re1—O22.027 (3)Re2—O62.021 (4)
Re1—N21.760 (4)Re2—N41.754 (4)
Re1—O41.921 (3)Re2—O81.936 (3)
Re1—P12.4220 (13)Re2—P22.4272 (13)
O1—C11.354 (6)O5—C391.347 (6)
C1—C21.396 (7)C39—C401.390 (7)
C1—C61.401 (7)C39—C441.405 (7)
C2—C31.382 (8)C40—C411.384 (8)
C2—H210.939C40—H4010.943
C3—C41.372 (9)C41—C421.375 (9)
C3—H24520.947C41—H4110.929
C4—C51.386 (8)C42—C431.377 (9)
C4—H410.931C42—H4210.919
C5—C61.386 (7)C43—C441.376 (8)
C5—H510.922C43—H4310.926
C6—N11.444 (7)C44—C2451.443 (9)
N1—C71.254 (7)C44—N1031.478 (6)
C7—C81.461 (8)N103—C1451.275 (7)
C7—H24530.945C145—C461.434 (7)
C8—C91.408 (8)C145—H14510.950
C8—C131.420 (8)C46—C471.421 (8)
C9—C101.365 (8)C46—C511.416 (7)
C9—H910.941C46—N2031.469 (9)
C10—C111.389 (9)C46—C471.421 (8)
C10—H1010.924C46—C511.416 (7)
C11—C121.373 (8)C47—C481.372 (10)
C11—H1110.929C47—H4710.927
C12—C131.400 (8)C48—C491.366 (11)
C12—H1210.938C48—H4810.940
C13—O21.326 (6)C49—C501.348 (9)
N2—C141.381 (6)C49—H4910.937
C14—C151.403 (7)C50—C511.390 (8)
C14—C191.398 (7)C50—H5010.934
C15—C161.374 (7)C51—O61.334 (6)
C15—H1510.939N4—C521.365 (6)
C16—C171.388 (8)C52—C531.413 (7)
C16—H1610.923C52—C571.401 (7)
C17—C181.381 (8)C53—C541.377 (7)
C17—H1710.938C53—H5310.931
C18—C191.396 (7)C54—C551.377 (8)
C18—H1810.927C54—H5410.947
C19—O31.347 (6)C55—C561.372 (8)
O3—H310.814C55—H5510.934
O4—C201.327 (7)C56—C571.390 (7)
C20—H2010.961C56—H5610.932
C20—H2030.957C57—O71.354 (6)
C20—H2020.959O7—H710.830
P1—C211.848 (5)O8—C581.404 (6)
P1—C271.828 (5)C58—H5820.965
P1—C331.822 (5)C58—H5810.973
C21—C221.371 (8)C58—H5830.973
C21—C261.376 (7)P2—C591.833 (5)
C22—C231.377 (8)P2—C651.826 (5)
C22—H2210.941P2—C711.819 (5)
C23—C241.386 (9)C59—C601.393 (7)
C23—H2310.935C59—C641.391 (7)
C24—C251.369 (9)C60—C611.384 (7)
C24—H2410.934C60—H6010.936
C25—C261.378 (8)C61—C621.380 (8)
C25—H2510.942C61—H6110.926
C26—H2610.926C62—C631.373 (8)
C27—C281.398 (7)C62—H6210.933
C27—C321.382 (7)C63—C641.382 (7)
C28—C291.377 (8)C63—H6310.928
C28—H2810.940C64—H6410.938
C29—C301.384 (8)C65—C661.389 (7)
C29—H2910.926C65—C701.390 (7)
C30—C311.368 (8)C66—C671.375 (7)
C30—H3010.932C66—H6610.940
C31—C321.392 (8)C67—C681.382 (8)
C31—H3110.928C67—H6710.932
C32—H3210.937C68—C691.375 (9)
C33—C341.387 (7)C68—H6810.930
C33—C381.397 (7)C69—C701.392 (8)
C34—C351.391 (7)C69—H6910.927
C34—H3410.938C70—H7010.929
C35—C361.386 (7)C71—C721.396 (7)
C35—H3510.929C71—C761.381 (7)
C36—C371.372 (8)C72—C731.389 (8)
C36—H3610.934C72—H7210.925
C37—C381.384 (7)C73—C741.377 (8)
C37—H3710.912C73—H7310.929
C38—H3810.934C74—C751.375 (8)
Re2—O52.084 (4)C74—H7410.938
Re2—O62.021 (4)C75—C761.388 (7)
Re2—N41.754 (4)C75—H7510.931
Re2—O81.936 (3)C76—H7610.936
Re2—P22.4272 (13)N203—C2451.256 (9)
Re2—N2032.214 (14)C245—H24510.950
O1—Re1—N179.17 (16)P2—Re2—N203162.8 (3)
O1—Re1—O2168.92 (14)O5—Re2—N10376.85 (17)
N1—Re1—O292.33 (16)O5—Re2—O6168.12 (14)
O1—Re1—N289.27 (16)N103—Re2—O694.75 (18)
N1—Re1—N297.22 (17)O5—Re2—N489.90 (17)
O2—Re1—N298.93 (17)N103—Re2—N497.1 (2)
O1—Re1—O483.63 (16)O6—Re2—N499.58 (17)
N1—Re1—O483.85 (16)O5—Re2—O884.34 (15)
O2—Re1—O488.43 (16)N103—Re2—O883.63 (19)
N2—Re1—O4172.49 (18)O6—Re2—O886.41 (15)
O1—Re1—P1101.51 (10)N4—Re2—O8173.86 (18)
N1—Re1—P1172.60 (12)O5—Re2—P295.64 (10)
O2—Re1—P186.01 (10)N103—Re2—P2169.50 (15)
N2—Re1—P190.16 (13)O6—Re2—P291.53 (11)
O4—Re1—P188.90 (11)N4—Re2—P290.08 (14)
Re1—O1—C1112.1 (3)O8—Re2—P288.38 (11)
O1—C1—C2119.2 (5)Re2—O5—C39115.3 (3)
O1—C1—C6122.6 (4)O5—C39—C40119.6 (5)
C2—C1—C6118.2 (5)O5—C39—C44122.1 (5)
C1—C2—C3120.2 (5)C40—C39—C44118.3 (5)
C1—C2—H21119.4C39—C40—C41120.7 (5)
C3—C2—H21120.4C39—C40—H401119.8
C2—C3—C4121.4 (5)C41—C40—H401119.5
C2—C3—H2452119.1C40—C41—C42120.1 (6)
C4—C3—H2452119.5C40—C41—H411118.8
C3—C4—C5119.2 (5)C42—C41—H411121.1
C3—C4—H41120.4C41—C42—C43119.9 (6)
C5—C4—H41120.3C41—C42—H421119.5
C4—C5—C6120.2 (6)C43—C42—H421120.6
C4—C5—H51120.7C42—C43—C44120.7 (6)
C6—C5—H51119.0C42—C43—H431119.5
C1—C6—C5120.7 (5)C44—C43—H431119.8
C1—C6—N1112.5 (4)C39—C44—C43120.1 (5)
C5—C6—N1126.9 (5)C39—C44—C245143.1 (8)
Re1—N1—C6113.3 (3)C43—C44—C24596.7 (8)
Re1—N1—C7123.3 (4)C39—C44—C43120.1 (5)
C6—N1—C7123.4 (5)C39—C44—N103108.6 (5)
N1—C7—C8126.0 (6)C43—C44—N103131.2 (5)
N1—C7—H2453117.7C44—N103—Re2116.4 (4)
C8—C7—H2453116.3C44—N103—C145121.1 (5)
C7—C8—C9113.9 (5)Re2—N103—C145122.5 (5)
C7—C8—C13126.6 (5)N103—C145—C46122.1 (6)
C9—C8—C13119.5 (5)N103—C145—H1451119.4
C8—C9—C10121.9 (6)C46—C145—H1451118.4
C8—C9—H91118.8C47—C46—C51118.2 (5)
C10—C9—H91119.2C47—C46—N203140.8 (8)
C9—C10—C11118.3 (6)C51—C46—N203101.0 (7)
C9—C10—H101121.1C145—C46—C47109.3 (5)
C11—C10—H101120.6C145—C46—C51132.2 (5)
C10—C11—C12121.5 (6)C47—C46—C51118.2 (5)
C10—C11—H111119.3C46—C47—C48121.0 (6)
C12—C11—H111119.2C46—C47—H471120.3
C11—C12—C13121.5 (6)C48—C47—H471118.7
C11—C12—H121119.4C47—C48—C49119.5 (6)
C13—C12—H121119.0C47—C48—H481119.1
C8—C13—C12117.2 (5)C49—C48—H481121.3
C8—C13—O2126.1 (5)C48—C49—C50121.0 (6)
C12—C13—O2116.7 (5)C48—C49—H491120.3
Re1—O2—C13123.0 (3)C50—C49—H491118.7
Re1—N2—C14167.1 (4)C49—C50—C51122.5 (6)
N2—C14—C15120.6 (4)C49—C50—H501120.7
N2—C14—C19120.0 (4)C51—C50—H501116.8
C15—C14—C19119.3 (5)C46—C51—C50117.9 (5)
C14—C15—C16120.7 (5)C46—C51—O6124.3 (5)
C14—C15—H151120.6C50—C51—O6117.8 (5)
C16—C15—H151118.7Re2—O6—C51121.1 (3)
C15—C16—C17119.7 (5)Re2—N4—C52167.3 (4)
C15—C16—H161119.3N4—C52—C53121.7 (5)
C17—C16—H161121.1N4—C52—C57120.2 (5)
C16—C17—C18120.7 (5)C53—C52—C57118.1 (5)
C16—C17—H171118.9C52—C53—C54121.2 (5)
C18—C17—H171120.5C52—C53—H531119.0
C17—C18—C19120.1 (5)C54—C53—H531119.7
C17—C18—H181120.8C53—C54—C55119.3 (5)
C19—C18—H181119.1C53—C54—H541119.7
C14—C19—C18119.5 (5)C55—C54—H541121.0
C14—C19—O3122.7 (4)C54—C55—C56121.1 (5)
C18—C19—O3117.8 (4)C54—C55—H551120.3
C19—O3—H31115.0C56—C55—H551118.6
Re1—O4—C20141.5 (4)C55—C56—C57120.4 (6)
O4—C20—H201108.9C55—C56—H561119.0
O4—C20—H203111.0C57—C56—H561120.6
H201—C20—H203108.9C52—C57—C56119.9 (5)
O4—C20—H202110.0C52—C57—O7121.4 (5)
H201—C20—H202109.0C56—C57—O7118.7 (5)
H203—C20—H202109.0C57—O7—H71116.5
Re1—P1—C21110.18 (17)Re2—O8—C58138.8 (4)
Re1—P1—C27115.27 (16)O8—C58—H582108.4
C21—P1—C27104.9 (2)O8—C58—H581111.3
Re1—P1—C33118.60 (16)H582—C58—H581109.4
C21—P1—C33102.8 (2)O8—C58—H583110.2
C27—P1—C33103.6 (2)H582—C58—H583109.0
P1—C21—C22117.9 (4)H581—C58—H583108.5
P1—C21—C26122.7 (4)Re2—P2—C59117.23 (16)
C22—C21—C26119.4 (5)Re2—P2—C65112.86 (16)
C21—C22—C23120.6 (5)C59—P2—C65101.1 (2)
C21—C22—H221119.9Re2—P2—C71114.13 (17)
C23—C22—H221119.5C59—P2—C71105.8 (2)
C22—C23—C24119.5 (6)C65—P2—C71104.1 (2)
C22—C23—H231119.8P2—C59—C60120.3 (4)
C24—C23—H231120.6P2—C59—C64120.4 (4)
C23—C24—C25120.0 (6)C60—C59—C64119.3 (5)
C23—C24—H241120.5C59—C60—C61120.1 (5)
C25—C24—H241119.5C59—C60—H601119.3
C24—C25—C26119.9 (6)C61—C60—H601120.6
C24—C25—H251120.7C60—C61—C62119.9 (5)
C26—C25—H251119.4C60—C61—H611119.4
C25—C26—C21120.5 (6)C62—C61—H611120.8
C25—C26—H261118.4C61—C62—C63120.5 (5)
C21—C26—H261121.1C61—C62—H621119.3
P1—C27—C28119.5 (4)C63—C62—H621120.2
P1—C27—C32121.5 (4)C62—C63—C64120.1 (5)
C28—C27—C32119.0 (5)C62—C63—H631119.4
C27—C28—C29120.5 (5)C64—C63—H631120.5
C27—C28—H281119.0C59—C64—C63120.1 (5)
C29—C28—H281120.5C59—C64—H641120.3
C28—C29—C30120.1 (5)C63—C64—H641119.6
C28—C29—H291121.0P2—C65—C66117.1 (4)
C30—C29—H291118.9P2—C65—C70123.8 (4)
C29—C30—C31119.9 (5)C66—C65—C70119.1 (5)
C29—C30—H301119.0C65—C66—C67120.5 (5)
C31—C30—H301121.1C65—C66—H661119.6
C30—C31—C32120.6 (6)C67—C66—H661119.9
C30—C31—H311119.0C66—C67—C68120.4 (6)
C32—C31—H311120.3C66—C67—H671120.2
C31—C32—C27119.9 (5)C68—C67—H671119.4
C31—C32—H321120.6C67—C68—C69119.7 (6)
C27—C32—H321119.5C67—C68—H681119.7
P1—C33—C34119.4 (4)C69—C68—H681120.6
P1—C33—C38121.4 (4)C68—C69—C70120.4 (5)
C34—C33—C38119.0 (5)C68—C69—H691118.9
C33—C34—C35119.6 (5)C70—C69—H691120.7
C33—C34—H341120.0C69—C70—C65119.8 (5)
C35—C34—H341120.4C69—C70—H701119.4
C34—C35—C36121.0 (5)C65—C70—H701120.8
C34—C35—H351120.0P2—C71—C72117.1 (4)
C36—C35—H351118.9P2—C71—C76125.1 (4)
C35—C36—C37119.3 (5)C72—C71—C76117.8 (5)
C35—C36—H361120.7C71—C72—C73121.4 (5)
C37—C36—H361120.0C71—C72—H721120.3
C36—C37—C38120.4 (5)C73—C72—H721118.3
C36—C37—H371119.7C72—C73—C74119.7 (5)
C38—C37—H371119.9C72—C73—H731119.0
C33—C38—C37120.7 (5)C74—C73—H731121.3
C33—C38—H381119.7C73—C74—C75119.5 (5)
C37—C38—H381119.6C73—C74—H741120.2
O5—Re2—O6168.12 (14)C75—C74—H741120.2
O5—Re2—N489.90 (17)C74—C75—C76120.8 (5)
O6—Re2—N499.58 (17)C74—C75—H751120.0
O5—Re2—O884.34 (15)C76—C75—H751119.3
O6—Re2—O886.41 (15)C75—C76—C71120.8 (5)
N4—Re2—O8173.86 (18)C75—C76—H761118.8
O5—Re2—P295.64 (10)C71—C76—H761120.4
O6—Re2—P291.53 (11)Re2—N203—C46121.1 (8)
N4—Re2—P290.08 (14)Re2—N203—C245115.4 (9)
O8—Re2—P288.38 (11)C46—N203—C245123.0 (11)
O5—Re2—N203101.1 (3)C44—C245—N203121.8 (12)
O6—Re2—N20371.3 (3)C44—C245—H2451119.5
N4—Re2—N20394.1 (4)N203—C245—H2451118.7
O8—Re2—N20389.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H31···O10.811.932.693 (8)156
O7—H71···O50.831.892.720 (8)177
C34—H341···O10.942.533.397 (8)153
C60—H601···N40.942.593.342 (8)137
C72—H721···O50.922.382.983 (8)123

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BR2071).

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