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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m313.
Published online 2008 January 9. doi:  10.1107/S160053680706802X
PMCID: PMC2960194

Tricarbonyl­chlorido{N-[2-(diphenyl­phosphino)benzyl­idene]benzyl­amine-κ2 N,P}rhenium(I) dichloro­methane solvate

Abstract

In the crystal structure of the title compound, [ReCl(C26H22NP)(CO)3]·CH2Cl2, the ReI atom exhibits a distorted octa­hedral environment defined by a facial arrangement of three carbonyl groups, a Cl atom and an N-[2-(diphenyl­phosphino)benzyl­idene]benzyl­amine ligand. The compound crystallizes with one CH2Cl2 mol­ecule per asymmetric unit. The benzyl­amine ligand and the ReI centre form a non-planar six-membered chelate ring.

Related literature

For related literature, see: Chen et al. (2001 [triangle]); and Schultz et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m313-scheme1.jpg

Experimental

Crystal data

  • [ReCl(C26H22NP)(CO)3]·CH2Cl2
  • M r = 770.03
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m313-efi1.jpg
  • a = 16.1971 (12) Å
  • b = 9.1981 (6) Å
  • c = 20.7977 (17) Å
  • β = 104.820 (9)°
  • V = 2995.4 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 4.41 mm−1
  • T = 296 K
  • 0.26 × 0.24 × 0.18 mm

Data collection

  • Stoe IPDS diffractometer
  • Absorption correction: analytical from crystal shape (IPDS; Stoe & Cie, 1998 [triangle]) T min = 0.431, T max = 0.612
  • 27893 measured reflections
  • 5789 independent reflections
  • 4647 reflections with I > 2σ(I)
  • R int = 0.089

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.081
  • S = 0.99
  • 5789 reflections
  • 355 parameters
  • H-atom parameters constrained
  • Δρmax = 1.27 e Å−3
  • Δρmin = −0.56 e Å−3

Data collection: IPDS (Stoe & Cie, 1998 [triangle]); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706802X/zl2094sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706802X/zl2094Isup2.hkl

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

supplementary crystallographic information

Comment

The iminophosphine ligand incorporated in the title compound, 2-(diphenylphosphino)benzylidenebenzylamine, is easily accessible by a condensation reaction of commercially available 2-(diphenylphoshino)benzaldehyde with benzylamine (Schultz et al., 2004). Without further purification the ligand is used for the preparation of the title complex starting from Re(CO)5Cl.

The crystals contain one molecule of CH2Cl2 per unit cell. The coordination geometry at the ReI atom is distorted octahedral with the three carbonyl ligands arranged in a facial fashion. Together with the ReI center the N,P-ligand forms a non-planar, six-membered chelate ring. The N—Re—P bite angle of 83.86 (12)° deviates from the ideal of 90° expected for an octahedron. The Re1—P1 and Re1—N1 bond lengths are 2.4561 (13) and 2.210 (4) Å, respectively. The Re—C bond length trans to the P atom (Re1—C29 1.942 (5) Å) is longer than its equivalents trans to the chloride and imine nitrogen atoms (Re1—C27 1.926 (6), Re1—C28 1.909 (6) Å) indicating stronger π-backbonding by the coordinated phosphine P atom. In its crystals, the complexes are linked to infinite chains via weak C—H···O intermolecular hydrogen bonds with a C···O distance of 3.327 (8) Å and a C22—H22···O3i angle of 149° (symmetry code: (i) x, y - 1, z). In summary, the structural characteristics are very similar to previously reported rhenium complexes of analogous chelating iminophosphine ligands (Chen et al., 2001).

Experimental

2-(Diphenylphosphino)benzaldehyde (95 mg, 0.33 mmol) and benzylamine (35 mg, 0.33 mmol) were stirred in dichloromethane. After 3 h the solvent was removed under reduced pressure. Degassed toluene (15 ml) and Re(CO)5Cl were added and the mixture was refluxed for 2 h under nitrogen atmosphere. After cooling to room temperature, the yellow precipitate was isolated by filtration and dried in vacuum. Recrystallization from dichloromethane/pentane yielded crystals suitable for X-ray crystallography. Yield: 206 mg (0.30 mmol, 91%). 1H-NMR (300 MHz, CDCl3): δ = 8.33 (s, 1 H, CH=N), 7.63–7.71 (m, 2 H, C6H4), 7.41–7.60 (m, 10 H, PPh2), 7.13–7.27 (m, 5 H, benzyl-Ph), 6.90–6.95 (m, 2 H, C6H4), 5.29 (s, 2 H, CH2); 31P{1H}-NMR (121 MHz, CDCl3): δ = 16.6; MS(EI): m/z (%) = 684.8 [M]+ (17.2), 656.8 [M—CO]+ (100), 628.8 [M-2CO]+ (94.2), 600.9 [M-3CO]+ (89.4), 564.9 [M-3CO-Cl]+ (7.3), 509.8 [M-3CO-Bn]+ (84.1), 91.0 [Bn]+ (50.8): EA (C29H22ClNO3PRe) calc.: C 50.84, H 3.24, N 2.04, found: C 50.27, H 3.32, N 1.95.

Refinement

The data were collected at room temperature. The structure was solved by direct methods (SIR97) and refined by full-matrix anisotropic least squares (SHELXL97).The H-atoms were placed in geometrically calculated positions and were refined using a riding model with C—H distances of 0.93 or 0.97 Å and isotropic displacement parameters Uiso equal to 1.2 times Ueq(C).

Figures

Fig. 1.
: View of the title compound with the atom numbering scheme. H-atoms have been omitted for clarity. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
Fig. 2.
: Excerpt from a cell plot depicting the intermolecular hydrogen-bond between H22 and the carbonyl oxygen atom O3 of a neighboring complex. The H atoms not involved in hydrogen bonding and the dichloromethane molecules have been omitted for clarity.

Crystal data

[ReCl(C26H22NP)(CO)3]·CH2Cl2F000 = 1504
Mr = 770.03Cell parameters were determined by indexing 8000 reflections with I/sigma limit 6.0.
Monoclinic, P21/cDx = 1.707 Mg m3
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 16.1971 (12) ÅCell parameters from 8000 reflections
b = 9.1981 (6) Åθ = 2.6–25.9º
c = 20.7977 (17) ŵ = 4.41 mm1
β = 104.820 (9)ºT = 296 K
V = 2995.4 (4) Å3Prism, faint yellow translucent
Z = 40.26 × 0.24 × 0.18 mm

Data collection

Stoe IPDS diffractometer5789 independent reflections
Radiation source: fine-focus sealed tube4647 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.090
T = 296(1) Kθmax = 25.9º
rotation scansθmin = 2.6º
Absorption correction: analyticalfrom crystal shape (IPDS; Stoe & Cie, 1998)h = −19→19
Tmin = 0.431, Tmax = 0.612k = −11→11
27893 measured reflectionsl = −25→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.081  w = 1/[σ2(Fo2) + (0.0449P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.003
5789 reflectionsΔρmax = 1.27 e Å3
355 parametersΔρmin = −0.56 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. Data were collected applying an imaging plate system (Stoe) with the following measurement parameters:Detector distance [mm] 70 Phi movement mode Oscillation Phi incr. [degrees] 1.0 Number of exposures 245 Irradiation / exposure [min] 1.00For a detailed description of the method see: Sheldrick, G.M., Paulus, E. Vertesy, L. & Hahn, F. (1995) Acta Cryst. B51, 89–98.
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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
Re10.76584 (1)0.11133 (2)0.96057 (1)0.0497 (1)
Cl10.87641 (8)0.10116 (16)1.06935 (6)0.0676 (4)
P10.71528 (7)−0.12810 (14)0.98633 (6)0.0497 (4)
O10.6469 (3)0.2883 (6)1.0245 (2)0.0955 (19)
O20.6302 (2)0.1448 (5)0.82923 (17)0.0709 (13)
O30.8385 (3)0.4027 (5)0.9260 (3)0.0873 (18)
N10.8596 (2)−0.0172 (5)0.92374 (18)0.0529 (13)
C10.8066 (3)−0.2456 (6)1.0211 (2)0.0533 (14)
C20.8029 (3)−0.3498 (7)1.0682 (3)0.0700 (19)
C30.8717 (4)−0.4415 (8)1.0951 (3)0.081 (2)
C40.9461 (4)−0.4281 (7)1.0746 (3)0.0762 (19)
C50.9499 (3)−0.3278 (7)1.0261 (3)0.0675 (16)
C60.8821 (3)−0.2341 (5)0.9988 (2)0.0542 (14)
C70.8968 (3)−0.1364 (6)0.9471 (2)0.0574 (18)
C80.8902 (3)0.0470 (6)0.8686 (2)0.0621 (16)
C90.8222 (3)0.0482 (6)0.8040 (2)0.0565 (17)
C100.8126 (5)0.1643 (8)0.7620 (3)0.088 (3)
C110.7522 (7)0.1629 (12)0.7011 (4)0.116 (4)
C120.6989 (6)0.0464 (12)0.6828 (4)0.107 (3)
C130.7084 (5)−0.0676 (10)0.7239 (4)0.098 (3)
C140.7691 (4)−0.0690 (7)0.7837 (3)0.074 (2)
C150.6533 (3)−0.1358 (6)1.0491 (2)0.0591 (18)
C160.5835 (3)−0.2249 (8)1.0432 (3)0.079 (2)
C170.5405 (4)−0.2269 (9)1.0929 (4)0.093 (3)
C180.5671 (4)−0.1411 (10)1.1476 (4)0.098 (3)
C190.6368 (5)−0.0521 (9)1.1547 (3)0.092 (3)
C200.6788 (4)−0.0498 (7)1.1043 (3)0.0739 (19)
C210.6505 (3)−0.2346 (5)0.9178 (2)0.0526 (14)
C220.6740 (4)−0.3688 (6)0.8994 (3)0.0706 (19)
C230.6192 (4)−0.4487 (8)0.8502 (3)0.089 (2)
C240.5409 (4)−0.3950 (7)0.8180 (3)0.082 (2)
C250.5170 (4)−0.2618 (8)0.8343 (3)0.080 (2)
C260.5704 (3)−0.1808 (7)0.8830 (3)0.0698 (17)
C270.6910 (3)0.2220 (7)1.0005 (3)0.0671 (19)
C280.6818 (3)0.1268 (5)0.8777 (3)0.0570 (16)
C290.8126 (3)0.2947 (6)0.9399 (3)0.0640 (16)
Cl20.8504 (2)−0.4410 (3)0.78245 (18)0.1549 (13)
Cl30.9854 (2)−0.2588 (5)0.7679 (2)0.197 (2)
C300.8967 (8)−0.3533 (13)0.7263 (5)0.149 (5)
H20.75310−0.359001.082400.0840*
H30.86760−0.511001.126600.0970*
H40.99320−0.486101.093300.0910*
H50.99910−0.322401.011100.0810*
H70.94020−0.165600.928100.0690*
H8A0.93880−0.008300.862900.0740*
H8B0.909100.145800.880200.0740*
H100.847000.245800.774400.1060*
H110.747900.241900.672500.1390*
H120.657000.046500.642700.1280*
H130.67310−0.148100.711600.1180*
H140.77430−0.150400.810900.0880*
H160.56520−0.283701.005900.0940*
H170.49330−0.287001.088900.1110*
H180.53770−0.142801.180600.1170*
H190.655500.005301.192400.1110*
H200.725400.011601.108200.0890*
H220.72740−0.406400.920400.0850*
H230.63590−0.539900.838800.1070*
H240.50420−0.449700.785200.0980*
H250.46380−0.224800.812200.0960*
H260.55330−0.088900.893100.0840*
H30A0.91260−0.424300.697200.1790*
H30B0.85580−0.286900.699100.1790*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Re10.0361 (1)0.0583 (1)0.0510 (1)0.0058 (1)0.0046 (1)−0.0049 (1)
Cl10.0481 (6)0.0854 (9)0.0596 (6)0.0045 (6)−0.0038 (5)−0.0101 (6)
P10.0351 (5)0.0620 (8)0.0503 (6)0.0073 (5)0.0076 (4)0.0006 (5)
O10.086 (3)0.117 (4)0.083 (3)0.042 (3)0.021 (2)−0.023 (2)
O20.0459 (17)0.103 (3)0.0553 (19)0.0123 (18)−0.0024 (15)0.0056 (18)
O30.064 (2)0.063 (3)0.131 (4)0.004 (2)0.018 (2)0.006 (2)
N10.0376 (18)0.065 (3)0.054 (2)0.0041 (18)0.0078 (15)−0.0065 (17)
C10.040 (2)0.064 (3)0.051 (2)0.010 (2)0.0028 (17)−0.0034 (19)
C20.059 (3)0.084 (4)0.067 (3)0.016 (3)0.016 (2)0.014 (3)
C30.076 (4)0.091 (4)0.071 (3)0.019 (3)0.011 (3)0.022 (3)
C40.060 (3)0.084 (4)0.075 (3)0.025 (3)0.000 (3)0.007 (3)
C50.045 (2)0.078 (3)0.074 (3)0.020 (3)0.005 (2)−0.007 (3)
C60.040 (2)0.064 (3)0.054 (2)0.008 (2)0.0034 (18)−0.004 (2)
C70.036 (2)0.072 (4)0.064 (3)0.006 (2)0.0126 (19)−0.010 (2)
C80.048 (2)0.070 (3)0.072 (3)−0.006 (2)0.022 (2)−0.003 (2)
C90.054 (3)0.060 (3)0.061 (3)0.007 (2)0.025 (2)−0.003 (2)
C100.099 (5)0.078 (4)0.095 (4)0.004 (4)0.037 (4)0.014 (4)
C110.140 (7)0.127 (7)0.085 (5)0.047 (6)0.037 (5)0.042 (5)
C120.101 (5)0.145 (8)0.069 (4)0.039 (6)0.011 (4)−0.002 (5)
C130.098 (5)0.111 (6)0.079 (4)−0.003 (4)0.010 (4)−0.028 (4)
C140.079 (4)0.071 (4)0.066 (3)−0.001 (3)0.010 (3)−0.007 (3)
C150.041 (2)0.079 (4)0.058 (3)0.013 (2)0.0141 (19)0.010 (2)
C160.050 (3)0.115 (5)0.071 (3)−0.004 (3)0.016 (2)0.013 (3)
C170.049 (3)0.146 (7)0.085 (4)0.003 (3)0.020 (3)0.029 (4)
C180.066 (4)0.158 (7)0.078 (4)0.041 (4)0.035 (3)0.031 (4)
C190.087 (5)0.129 (6)0.069 (4)0.032 (4)0.034 (3)0.006 (4)
C200.068 (3)0.093 (4)0.064 (3)0.015 (3)0.023 (3)0.000 (3)
C210.044 (2)0.058 (3)0.053 (2)0.002 (2)0.0072 (18)0.0029 (19)
C220.060 (3)0.070 (4)0.074 (3)0.012 (3)0.003 (2)−0.009 (2)
C230.091 (4)0.072 (4)0.094 (4)0.004 (4)0.006 (4)−0.020 (3)
C240.080 (4)0.086 (4)0.067 (3)−0.018 (3)−0.002 (3)0.001 (3)
C250.052 (3)0.093 (5)0.080 (4)0.001 (3)−0.008 (3)0.002 (3)
C260.049 (3)0.072 (3)0.079 (3)0.009 (3)−0.001 (2)−0.003 (3)
C270.055 (3)0.080 (4)0.059 (3)0.010 (3)0.001 (2)−0.006 (2)
C280.048 (2)0.060 (3)0.065 (3)0.004 (2)0.018 (2)−0.002 (2)
C290.041 (2)0.062 (3)0.083 (3)0.008 (2)0.005 (2)−0.005 (3)
Cl20.146 (2)0.1108 (18)0.195 (3)−0.0005 (17)0.020 (2)0.0389 (19)
Cl30.110 (2)0.214 (4)0.268 (5)−0.026 (2)0.053 (2)−0.016 (3)
C300.168 (10)0.164 (10)0.104 (6)−0.014 (8)0.013 (6)−0.014 (6)

Geometric parameters (Å, °)

Re1—Cl12.5024 (13)C17—C181.361 (12)
Re1—P12.4561 (13)C18—C191.372 (11)
Re1—N12.210 (4)C19—C201.388 (10)
Re1—C271.926 (6)C21—C261.404 (7)
Re1—C281.909 (6)C21—C221.375 (7)
Re1—C291.942 (5)C22—C231.382 (9)
Cl2—C301.739 (12)C23—C241.366 (9)
Cl3—C301.712 (13)C24—C251.354 (10)
P1—C211.824 (5)C25—C261.372 (9)
P1—C11.825 (5)C2—H20.9300
P1—C151.841 (5)C3—H30.9300
O1—C271.146 (8)C4—H40.9300
O2—C281.145 (7)C5—H50.9300
O3—C291.144 (7)C7—H70.9300
N1—C71.285 (7)C8—H8B0.9700
N1—C81.483 (6)C8—H8A0.9700
C1—C61.418 (7)C10—H100.9300
C1—C21.383 (8)C11—H110.9300
C2—C31.396 (9)C12—H120.9300
C3—C41.383 (9)C13—H130.9300
C4—C51.380 (9)C14—H140.9300
C5—C61.397 (7)C16—H160.9300
C6—C71.467 (6)C17—H170.9300
C8—C91.504 (6)C18—H180.9300
C9—C141.376 (8)C19—H190.9300
C9—C101.363 (9)C20—H200.9300
C10—C111.388 (11)C22—H220.9300
C11—C121.368 (15)C23—H230.9300
C12—C131.337 (13)C24—H240.9300
C13—C141.374 (10)C25—H250.9300
C15—C161.376 (8)C26—H260.9300
C15—C201.368 (8)C30—H30A0.9700
C16—C171.386 (9)C30—H30B0.9700
Re1···C144.048 (6)C29···C83.150 (8)
Re1···H203.4200C29···Cl13.172 (6)
Cl1···P13.4546 (19)C29···C282.673 (8)
Cl1···N13.164 (4)C29···C272.680 (8)
Cl1···C13.447 (6)C29···N13.009 (7)
Cl1···C63.426 (5)C1···H222.6200
Cl1···C73.432 (5)C2···H30Biv2.9200
Cl1···C273.179 (6)C2···H223.0500
Cl1···C293.172 (6)C3···H30Biv3.0700
Cl2···O3i3.363 (7)C5···H8Biii3.0900
Cl3···C10ii3.554 (9)C6···H223.0600
Cl1···H202.8900C7···H143.0200
Cl1···H8Aiii3.0800C11···H3x3.0500
Cl1···H30Aiv3.0400C12···H2x3.0100
Cl1···H7iii3.0200C15···H22.6000
Cl2···H10i2.8900C16···H22.9300
Cl2···H143.0600C17···H13iv3.0500
Cl3···H10ii3.0600C18···H13iv2.7000
P1···C73.247 (5)C18···H26v2.8500
P1···C273.267 (7)C19···H13iv3.0000
P1···Cl13.4546 (19)C21···H162.6000
P1···N13.123 (4)C24···H18x2.8700
P1···C283.205 (5)C26···H162.7500
O2···C133.412 (9)C27···H202.9000
O2···C93.402 (6)C28···H262.9500
O2···C143.304 (8)C29···H22vi3.0600
O2···C18v3.352 (8)C29···H8B2.6200
O3···C22vi3.327 (8)C29···H5iii2.9700
O3···Cl2vi3.363 (7)H2···C152.6000
O3···C5iii3.386 (7)H2···C162.9300
O1···H17v2.8200H2···C12iv3.0100
O1···H12vii2.8600H3···C11iv3.0500
O2···H18v2.6700H5···O3iii2.7200
O2···H23vi2.9100H5···C29iii2.9700
O2···H24viii2.9200H5···H72.2600
O3···H8B2.8900H7···H8A1.9800
O3···H22vi2.5000H7···Cl1iii3.0200
O3···H5iii2.7200H7···H52.2600
N1···P13.123 (4)H8A···Cl1iii3.0800
N1···Cl13.164 (4)H8A···H71.9800
N1···C13.184 (6)H8B···C292.6200
N1···C283.091 (6)H8B···O32.8900
N1···C293.009 (7)H8B···H102.3600
N1···H142.6900H8B···C5iii3.0900
C5···O3iii3.386 (7)H10···Cl3ix3.0600
C6···Cl13.426 (5)H10···Cl2vi2.8900
C7···C143.552 (7)H10···H8B2.3600
C9···O23.402 (6)H12···O1xi2.8600
C9···C283.135 (7)H13···C18x2.7000
C10···Cl3ix3.554 (9)H13···C19x3.0000
C13···O23.412 (9)H13···C17x3.0500
C14···Re14.048 (6)H14···N12.6900
C14···C283.237 (8)H14···C73.0200
C14···C73.552 (7)H14···Cl23.0600
C14···O23.304 (8)H16···C262.7500
C16···C263.309 (9)H16···C212.6000
C18···O2v3.352 (8)H17···O1v2.8200
C20···C273.342 (9)H18···O2v2.6700
C22···O3i3.327 (8)H18···C24iv2.8700
C26···C283.373 (8)H18···H24iv2.5200
C26···C163.309 (9)H20···Re13.4200
C27···P13.267 (7)H20···C272.9000
C27···C153.541 (8)H20···Cl12.8900
C27···C282.668 (8)H22···C12.6200
C27···C203.342 (9)H22···C23.0500
C27···Cl13.179 (6)H22···O3i2.5000
C27···C292.680 (8)H22···C29i3.0600
C28···C83.507 (7)H22···C63.0600
C28···C143.237 (8)H23···O2i2.9100
C28···P13.205 (5)H24···H18x2.5200
C28···C263.373 (8)H24···O2xii2.9200
C28···C213.496 (7)H26···C18v2.8500
C28···C93.135 (7)H26···C282.9500
C28···C272.668 (8)H30A···Cl1x3.0400
C28···C292.673 (8)H30B···C2x2.9200
C28···N13.091 (6)H30B···C3x3.0700
Cl1—Re1—P188.32 (4)C23—C24—C25119.6 (6)
Cl1—Re1—N184.09 (10)C24—C25—C26120.7 (6)
Cl1—Re1—C2790.79 (18)C21—C26—C25121.0 (6)
Cl1—Re1—C28177.87 (14)Re1—C27—O1179.6 (4)
Cl1—Re1—C2990.18 (18)Re1—C28—O2175.6 (4)
P1—Re1—N183.86 (12)Re1—C29—O3178.1 (6)
P1—Re1—C2795.63 (19)C1—C2—H2119.00
P1—Re1—C2893.63 (15)C3—C2—H2119.00
P1—Re1—C29176.34 (16)C2—C3—H3120.00
N1—Re1—C27174.9 (2)C4—C3—H3120.00
N1—Re1—C2896.98 (18)C3—C4—H4120.00
N1—Re1—C2992.66 (19)C5—C4—H4120.00
C27—Re1—C2888.2 (2)C4—C5—H5119.00
C27—Re1—C2987.7 (2)C6—C5—H5119.00
C28—Re1—C2987.9 (2)N1—C7—H7115.00
Re1—P1—C1109.62 (17)C6—C7—H7115.00
Re1—P1—C15117.52 (18)N1—C8—H8A109.00
Re1—P1—C21117.93 (15)N1—C8—H8B109.00
C1—P1—C15103.3 (2)C9—C8—H8A109.00
C1—P1—C21103.7 (2)C9—C8—H8B109.00
C15—P1—C21103.0 (2)H8A—C8—H8B108.00
Re1—N1—C7128.5 (3)C9—C10—H10119.00
Re1—N1—C8116.7 (3)C11—C10—H10120.00
C7—N1—C8114.5 (4)C10—C11—H11120.00
P1—C1—C2120.9 (4)C12—C11—H11120.00
P1—C1—C6120.4 (4)C11—C12—H12121.00
C2—C1—C6118.7 (5)C13—C12—H12121.00
C1—C2—C3121.9 (5)C12—C13—H13119.00
C2—C3—C4119.5 (6)C14—C13—H13119.00
C3—C4—C5119.4 (6)C9—C14—H14119.00
C4—C5—C6122.2 (5)C13—C14—H14119.00
C1—C6—C5118.4 (4)C15—C16—H16120.00
C1—C6—C7126.9 (4)C17—C16—H16120.00
C5—C6—C7114.7 (4)C16—C17—H17120.00
N1—C7—C6130.7 (4)C18—C17—H17120.00
N1—C8—C9112.4 (4)C17—C18—H18120.00
C8—C9—C10121.0 (5)C19—C18—H18120.00
C8—C9—C14121.7 (5)C18—C19—H19121.00
C10—C9—C14117.2 (5)C20—C19—H19121.00
C9—C10—C11121.0 (7)C15—C20—H20119.00
C10—C11—C12120.6 (9)C19—C20—H20119.00
C11—C12—C13118.4 (8)C21—C22—H22120.00
C12—C13—C14121.7 (8)C23—C22—H22120.00
C9—C14—C13121.1 (6)C22—C23—H23120.00
P1—C15—C16123.0 (4)C24—C23—H23120.00
P1—C15—C20118.1 (4)C23—C24—H24120.00
C16—C15—C20118.9 (5)C25—C24—H24120.00
C15—C16—C17120.0 (6)C24—C25—H25120.00
C16—C17—C18120.2 (7)C26—C25—H25120.00
C17—C18—C19120.8 (7)C21—C26—H26120.00
C18—C19—C20118.5 (7)C25—C26—H26120.00
C15—C20—C19121.6 (6)Cl2—C30—Cl3110.3 (6)
P1—C21—C22123.7 (4)Cl2—C30—H30A110.00
P1—C21—C26119.0 (4)Cl2—C30—H30B110.00
C22—C21—C26117.3 (5)Cl3—C30—H30A110.00
C21—C22—C23120.8 (6)Cl3—C30—H30B110.00
C22—C23—C24120.7 (6)H30A—C30—H30B108.00
Cl1—Re1—P1—C1−42.83 (15)Re1—N1—C7—C68.8 (8)
N1—Re1—P1—C141.41 (18)C2—C1—C6—C7176.7 (5)
C27—Re1—P1—C1−133.5 (2)C2—C1—C6—C5−0.7 (7)
C28—Re1—P1—C1138.1 (2)P1—C1—C2—C3179.5 (5)
Cl1—Re1—P1—C1574.62 (17)C6—C1—C2—C31.2 (8)
N1—Re1—P1—C15158.86 (19)P1—C1—C6—C5−179.0 (4)
C27—Re1—P1—C15−16.0 (2)P1—C1—C6—C7−1.6 (7)
C28—Re1—P1—C15−104.5 (2)C1—C2—C3—C40.3 (10)
Cl1—Re1—P1—C21−161.14 (19)C2—C3—C4—C5−2.4 (10)
N1—Re1—P1—C21−76.9 (2)C3—C4—C5—C62.9 (9)
C27—Re1—P1—C21108.2 (3)C4—C5—C6—C7−179.1 (5)
C28—Re1—P1—C2119.7 (2)C4—C5—C6—C1−1.3 (8)
Cl1—Re1—N1—C753.1 (4)C5—C6—C7—N1−161.0 (5)
P1—Re1—N1—C7−35.9 (4)C1—C6—C7—N121.6 (8)
C28—Re1—N1—C7−128.8 (4)N1—C8—C9—C10139.8 (6)
C29—Re1—N1—C7143.0 (4)N1—C8—C9—C14−42.4 (7)
Cl1—Re1—N1—C8−121.0 (3)C14—C9—C10—C11−0.6 (10)
P1—Re1—N1—C8150.1 (3)C8—C9—C10—C11177.3 (7)
C28—Re1—N1—C857.2 (3)C10—C9—C14—C13−0.8 (9)
C29—Re1—N1—C8−31.0 (3)C8—C9—C14—C13−178.6 (6)
Re1—P1—C1—C2147.4 (4)C9—C10—C11—C122.2 (14)
C15—P1—C1—C221.4 (5)C10—C11—C12—C13−2.2 (15)
C21—P1—C1—C2−85.8 (5)C11—C12—C13—C140.9 (14)
Re1—P1—C1—C6−34.3 (4)C12—C13—C14—C90.7 (12)
C15—P1—C1—C6−160.4 (4)P1—C15—C16—C17179.0 (5)
C21—P1—C1—C692.5 (4)C16—C15—C20—C191.0 (9)
C1—P1—C15—C2080.7 (5)C20—C15—C16—C17−0.3 (9)
C21—P1—C15—C20−171.5 (4)P1—C15—C20—C19−178.3 (5)
Re1—P1—C15—C20−40.1 (5)C15—C16—C17—C18−0.1 (11)
Re1—P1—C21—C22118.7 (4)C16—C17—C18—C19−0.3 (12)
C1—P1—C21—C22−2.7 (5)C17—C18—C19—C201.0 (12)
C15—P1—C21—C22−110.1 (5)C18—C19—C20—C15−1.4 (11)
Re1—P1—C21—C26−63.9 (4)P1—C21—C22—C23175.2 (5)
C1—P1—C21—C26174.7 (4)C26—C21—C22—C23−2.2 (8)
C15—P1—C21—C2667.3 (4)P1—C21—C26—C25−175.3 (5)
C21—P1—C15—C169.2 (5)C22—C21—C26—C252.2 (8)
Re1—P1—C15—C16140.6 (4)C21—C22—C23—C241.0 (10)
C1—P1—C15—C16−98.6 (5)C22—C23—C24—C250.3 (10)
C7—N1—C8—C9114.7 (5)C23—C24—C25—C26−0.4 (10)
Re1—N1—C8—C9−70.4 (5)C24—C25—C26—C21−0.9 (9)
C8—N1—C7—C6−177.1 (5)

Symmetry codes: (i) x, y−1, z; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+2, −y, −z+2; (iv) x, −y−1/2, z+1/2; (v) −x+1, −y, −z+2; (vi) x, y+1, z; (vii) x, −y+1/2, z+1/2; (viii) −x+1, y+1/2, −z+3/2; (ix) −x+2, y+1/2, −z+3/2; (x) x, −y−1/2, z−1/2; (xi) x, −y+1/2, z−1/2; (xii) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C22—H22···O3i0.932.503.327 (8)149

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2094).

References

  • 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.
  • Chen, X., Femia, F. J., Babich, J. W. & Zubieta, J. (2001). Inorg. Chim. Acta, 315, 147–152. [PMC free article] [PubMed]
  • Schultz, T., Schmees, N. & Pfaltz, A. (2004). Appl. Organomet. Chem.18, 595–601.
  • Sheldrick, G. M. (1997). SHELXL97 University of Göttingen, Germany. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Stoe & Cie (1998). IPDS Version 2.89. Stoe & Cie, Darmstadt, Germany.

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