metal-organic compounds
Tricarbonylchlorido{N-[2-(diphenylphosphino)benzylidene]benzylamine-κ2N,P}rhenium(I) dichloromethane solvate
aJohannes Kepler Universität Linz, Institut für Anorganische Chemie, Altenbergerstrasse 69, 4040 Linz, Austria, and bUniversität Regensburg, Zentrale Analytik, Röntgenstrukturanalyse, Universitätsstrasse 31, 93053 Regensburg, Germany
*Correspondence e-mail: uwe.monkowius@jku.at
In the 26H22NP)(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 The benzylamine ligand and the ReI centre form a non-planar six-membered chelate ring.
of the title compound, [ReCl(CExperimental
Crystal data
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Refinement
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Data collection: IPDS (Stoe & Cie, 1998); cell IPDS; data reduction: IPDS; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Supporting information
10.1107/S160053680706802X/zl2094sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680706802X/zl2094Isup2.hkl
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.
The data were collected at room temperature. The structure was solved by
(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).Data collection: IPDS (Stoe & Cie, 1998); cell
IPDS (Stoe & Cie, 1998); data reduction: IPDS (Stoe & Cie, 1998); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).[ReCl(C26H22NP)(CO)3]·CH2Cl2 | F(000) = 1504 |
Mr = 770.03 | Cell parameters were determined by indexing 8000 reflections with I/sigma limit 6.0. |
Monoclinic, P21/c | Dx = 1.707 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.1971 (12) Å | Cell parameters from 8000 reflections |
b = 9.1981 (6) Å | θ = 2.6–25.9° |
c = 20.7977 (17) Å | µ = 4.41 mm−1 |
β = 104.820 (9)° | T = 296 K |
V = 2995.4 (4) Å3 | Prism, faint yellow translucent |
Z = 4 | 0.26 × 0.24 × 0.18 mm |
Stoe IPDS diffractometer | 5789 independent reflections |
Radiation source: fine-focus sealed tube | 4647 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.090 |
rotation scans | θmax = 25.9°, θmin = 2.6° |
Absorption correction: analytical from crystal shape (IPDS; Stoe & Cie, 1998) | h = −19→19 |
Tmin = 0.431, Tmax = 0.612 | k = −11→11 |
27893 measured reflections | l = −25→25 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0449P)2] where P = (Fo2 + 2Fc2)/3 |
5789 reflections | (Δ/σ)max = 0.003 |
355 parameters | Δρmax = 1.27 e Å−3 |
0 restraints | Δρmin = −0.56 e Å−3 |
[ReCl(C26H22NP)(CO)3]·CH2Cl2 | V = 2995.4 (4) Å3 |
Mr = 770.03 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.1971 (12) Å | µ = 4.41 mm−1 |
b = 9.1981 (6) Å | T = 296 K |
c = 20.7977 (17) Å | 0.26 × 0.24 × 0.18 mm |
β = 104.820 (9)° |
Stoe IPDS diffractometer | 5789 independent reflections |
Absorption correction: analytical from crystal shape (IPDS; Stoe & Cie, 1998) | 4647 reflections with I > 2σ(I) |
Tmin = 0.431, Tmax = 0.612 | Rint = 0.090 |
27893 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 0.99 | Δρmax = 1.27 e Å−3 |
5789 reflections | Δρmin = −0.56 e Å−3 |
355 parameters |
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] 1.00 For 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. |
x | y | z | Uiso*/Ueq | ||
Re1 | 0.76584 (1) | 0.11133 (2) | 0.96057 (1) | 0.0497 (1) | |
Cl1 | 0.87641 (8) | 0.10116 (16) | 1.06935 (6) | 0.0676 (4) | |
P1 | 0.71528 (7) | −0.12810 (14) | 0.98633 (6) | 0.0497 (4) | |
O1 | 0.6469 (3) | 0.2883 (6) | 1.0245 (2) | 0.0955 (19) | |
O2 | 0.6302 (2) | 0.1448 (5) | 0.82923 (17) | 0.0709 (13) | |
O3 | 0.8385 (3) | 0.4027 (5) | 0.9260 (3) | 0.0873 (18) | |
N1 | 0.8596 (2) | −0.0172 (5) | 0.92374 (18) | 0.0529 (13) | |
C1 | 0.8066 (3) | −0.2456 (6) | 1.0211 (2) | 0.0533 (14) | |
C2 | 0.8029 (3) | −0.3498 (7) | 1.0682 (3) | 0.0700 (19) | |
C3 | 0.8717 (4) | −0.4415 (8) | 1.0951 (3) | 0.081 (2) | |
C4 | 0.9461 (4) | −0.4281 (7) | 1.0746 (3) | 0.0762 (19) | |
C5 | 0.9499 (3) | −0.3278 (7) | 1.0261 (3) | 0.0675 (16) | |
C6 | 0.8821 (3) | −0.2341 (5) | 0.9988 (2) | 0.0542 (14) | |
C7 | 0.8968 (3) | −0.1364 (6) | 0.9471 (2) | 0.0574 (18) | |
C8 | 0.8902 (3) | 0.0470 (6) | 0.8686 (2) | 0.0621 (16) | |
C9 | 0.8222 (3) | 0.0482 (6) | 0.8040 (2) | 0.0565 (17) | |
C10 | 0.8126 (5) | 0.1643 (8) | 0.7620 (3) | 0.088 (3) | |
C11 | 0.7522 (7) | 0.1629 (12) | 0.7011 (4) | 0.116 (4) | |
C12 | 0.6989 (6) | 0.0464 (12) | 0.6828 (4) | 0.107 (3) | |
C13 | 0.7084 (5) | −0.0676 (10) | 0.7239 (4) | 0.098 (3) | |
C14 | 0.7691 (4) | −0.0690 (7) | 0.7837 (3) | 0.074 (2) | |
C15 | 0.6533 (3) | −0.1358 (6) | 1.0491 (2) | 0.0591 (18) | |
C16 | 0.5835 (3) | −0.2249 (8) | 1.0432 (3) | 0.079 (2) | |
C17 | 0.5405 (4) | −0.2269 (9) | 1.0929 (4) | 0.093 (3) | |
C18 | 0.5671 (4) | −0.1411 (10) | 1.1476 (4) | 0.098 (3) | |
C19 | 0.6368 (5) | −0.0521 (9) | 1.1547 (3) | 0.092 (3) | |
C20 | 0.6788 (4) | −0.0498 (7) | 1.1043 (3) | 0.0739 (19) | |
C21 | 0.6505 (3) | −0.2346 (5) | 0.9178 (2) | 0.0526 (14) | |
C22 | 0.6740 (4) | −0.3688 (6) | 0.8994 (3) | 0.0706 (19) | |
C23 | 0.6192 (4) | −0.4487 (8) | 0.8502 (3) | 0.089 (2) | |
C24 | 0.5409 (4) | −0.3950 (7) | 0.8180 (3) | 0.082 (2) | |
C25 | 0.5170 (4) | −0.2618 (8) | 0.8343 (3) | 0.080 (2) | |
C26 | 0.5704 (3) | −0.1808 (7) | 0.8830 (3) | 0.0698 (17) | |
C27 | 0.6910 (3) | 0.2220 (7) | 1.0005 (3) | 0.0671 (19) | |
C28 | 0.6818 (3) | 0.1268 (5) | 0.8777 (3) | 0.0570 (16) | |
C29 | 0.8126 (3) | 0.2947 (6) | 0.9399 (3) | 0.0640 (16) | |
Cl2 | 0.8504 (2) | −0.4410 (3) | 0.78245 (18) | 0.1549 (13) | |
Cl3 | 0.9854 (2) | −0.2588 (5) | 0.7679 (2) | 0.197 (2) | |
C30 | 0.8967 (8) | −0.3533 (13) | 0.7263 (5) | 0.149 (5) | |
H2 | 0.75310 | −0.35900 | 1.08240 | 0.0840* | |
H3 | 0.86760 | −0.51100 | 1.12660 | 0.0970* | |
H4 | 0.99320 | −0.48610 | 1.09330 | 0.0910* | |
H5 | 0.99910 | −0.32240 | 1.01110 | 0.0810* | |
H7 | 0.94020 | −0.16560 | 0.92810 | 0.0690* | |
H8A | 0.93880 | −0.00830 | 0.86290 | 0.0740* | |
H8B | 0.90910 | 0.14580 | 0.88020 | 0.0740* | |
H10 | 0.84700 | 0.24580 | 0.77440 | 0.1060* | |
H11 | 0.74790 | 0.24190 | 0.67250 | 0.1390* | |
H12 | 0.65700 | 0.04650 | 0.64270 | 0.1280* | |
H13 | 0.67310 | −0.14810 | 0.71160 | 0.1180* | |
H14 | 0.77430 | −0.15040 | 0.81090 | 0.0880* | |
H16 | 0.56520 | −0.28370 | 1.00590 | 0.0940* | |
H17 | 0.49330 | −0.28700 | 1.08890 | 0.1110* | |
H18 | 0.53770 | −0.14280 | 1.18060 | 0.1170* | |
H19 | 0.65550 | 0.00530 | 1.19240 | 0.1110* | |
H20 | 0.72540 | 0.01160 | 1.10820 | 0.0890* | |
H22 | 0.72740 | −0.40640 | 0.92040 | 0.0850* | |
H23 | 0.63590 | −0.53990 | 0.83880 | 0.1070* | |
H24 | 0.50420 | −0.44970 | 0.78520 | 0.0980* | |
H25 | 0.46380 | −0.22480 | 0.81220 | 0.0960* | |
H26 | 0.55330 | −0.08890 | 0.89310 | 0.0840* | |
H30A | 0.91260 | −0.42430 | 0.69720 | 0.1790* | |
H30B | 0.85580 | −0.28690 | 0.69910 | 0.1790* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Re1 | 0.0361 (1) | 0.0583 (1) | 0.0510 (1) | 0.0058 (1) | 0.0046 (1) | −0.0049 (1) |
Cl1 | 0.0481 (6) | 0.0854 (9) | 0.0596 (6) | 0.0045 (6) | −0.0038 (5) | −0.0101 (6) |
P1 | 0.0351 (5) | 0.0620 (8) | 0.0503 (6) | 0.0073 (5) | 0.0076 (4) | 0.0006 (5) |
O1 | 0.086 (3) | 0.117 (4) | 0.083 (3) | 0.042 (3) | 0.021 (2) | −0.023 (2) |
O2 | 0.0459 (17) | 0.103 (3) | 0.0553 (19) | 0.0123 (18) | −0.0024 (15) | 0.0056 (18) |
O3 | 0.064 (2) | 0.063 (3) | 0.131 (4) | 0.004 (2) | 0.018 (2) | 0.006 (2) |
N1 | 0.0376 (18) | 0.065 (3) | 0.054 (2) | 0.0041 (18) | 0.0078 (15) | −0.0065 (17) |
C1 | 0.040 (2) | 0.064 (3) | 0.051 (2) | 0.010 (2) | 0.0028 (17) | −0.0034 (19) |
C2 | 0.059 (3) | 0.084 (4) | 0.067 (3) | 0.016 (3) | 0.016 (2) | 0.014 (3) |
C3 | 0.076 (4) | 0.091 (4) | 0.071 (3) | 0.019 (3) | 0.011 (3) | 0.022 (3) |
C4 | 0.060 (3) | 0.084 (4) | 0.075 (3) | 0.025 (3) | 0.000 (3) | 0.007 (3) |
C5 | 0.045 (2) | 0.078 (3) | 0.074 (3) | 0.020 (3) | 0.005 (2) | −0.007 (3) |
C6 | 0.040 (2) | 0.064 (3) | 0.054 (2) | 0.008 (2) | 0.0034 (18) | −0.004 (2) |
C7 | 0.036 (2) | 0.072 (4) | 0.064 (3) | 0.006 (2) | 0.0126 (19) | −0.010 (2) |
C8 | 0.048 (2) | 0.070 (3) | 0.072 (3) | −0.006 (2) | 0.022 (2) | −0.003 (2) |
C9 | 0.054 (3) | 0.060 (3) | 0.061 (3) | 0.007 (2) | 0.025 (2) | −0.003 (2) |
C10 | 0.099 (5) | 0.078 (4) | 0.095 (4) | 0.004 (4) | 0.037 (4) | 0.014 (4) |
C11 | 0.140 (7) | 0.127 (7) | 0.085 (5) | 0.047 (6) | 0.037 (5) | 0.042 (5) |
C12 | 0.101 (5) | 0.145 (8) | 0.069 (4) | 0.039 (6) | 0.011 (4) | −0.002 (5) |
C13 | 0.098 (5) | 0.111 (6) | 0.079 (4) | −0.003 (4) | 0.010 (4) | −0.028 (4) |
C14 | 0.079 (4) | 0.071 (4) | 0.066 (3) | −0.001 (3) | 0.010 (3) | −0.007 (3) |
C15 | 0.041 (2) | 0.079 (4) | 0.058 (3) | 0.013 (2) | 0.0141 (19) | 0.010 (2) |
C16 | 0.050 (3) | 0.115 (5) | 0.071 (3) | −0.004 (3) | 0.016 (2) | 0.013 (3) |
C17 | 0.049 (3) | 0.146 (7) | 0.085 (4) | 0.003 (3) | 0.020 (3) | 0.029 (4) |
C18 | 0.066 (4) | 0.158 (7) | 0.078 (4) | 0.041 (4) | 0.035 (3) | 0.031 (4) |
C19 | 0.087 (5) | 0.129 (6) | 0.069 (4) | 0.032 (4) | 0.034 (3) | 0.006 (4) |
C20 | 0.068 (3) | 0.093 (4) | 0.064 (3) | 0.015 (3) | 0.023 (3) | 0.000 (3) |
C21 | 0.044 (2) | 0.058 (3) | 0.053 (2) | 0.002 (2) | 0.0072 (18) | 0.0029 (19) |
C22 | 0.060 (3) | 0.070 (4) | 0.074 (3) | 0.012 (3) | 0.003 (2) | −0.009 (2) |
C23 | 0.091 (4) | 0.072 (4) | 0.094 (4) | 0.004 (4) | 0.006 (4) | −0.020 (3) |
C24 | 0.080 (4) | 0.086 (4) | 0.067 (3) | −0.018 (3) | −0.002 (3) | 0.001 (3) |
C25 | 0.052 (3) | 0.093 (5) | 0.080 (4) | 0.001 (3) | −0.008 (3) | 0.002 (3) |
C26 | 0.049 (3) | 0.072 (3) | 0.079 (3) | 0.009 (3) | −0.001 (2) | −0.003 (3) |
C27 | 0.055 (3) | 0.080 (4) | 0.059 (3) | 0.010 (3) | 0.001 (2) | −0.006 (2) |
C28 | 0.048 (2) | 0.060 (3) | 0.065 (3) | 0.004 (2) | 0.018 (2) | −0.002 (2) |
C29 | 0.041 (2) | 0.062 (3) | 0.083 (3) | 0.008 (2) | 0.005 (2) | −0.005 (3) |
Cl2 | 0.146 (2) | 0.1108 (18) | 0.195 (3) | −0.0005 (17) | 0.020 (2) | 0.0389 (19) |
Cl3 | 0.110 (2) | 0.214 (4) | 0.268 (5) | −0.026 (2) | 0.053 (2) | −0.016 (3) |
C30 | 0.168 (10) | 0.164 (10) | 0.104 (6) | −0.014 (8) | 0.013 (6) | −0.014 (6) |
Re1—Cl1 | 2.5024 (13) | C17—C18 | 1.361 (12) |
Re1—P1 | 2.4561 (13) | C18—C19 | 1.372 (11) |
Re1—N1 | 2.210 (4) | C19—C20 | 1.388 (10) |
Re1—C27 | 1.926 (6) | C21—C26 | 1.404 (7) |
Re1—C28 | 1.909 (6) | C21—C22 | 1.375 (7) |
Re1—C29 | 1.942 (5) | C22—C23 | 1.382 (9) |
Cl2—C30 | 1.739 (12) | C23—C24 | 1.366 (9) |
Cl3—C30 | 1.712 (13) | C24—C25 | 1.354 (10) |
P1—C21 | 1.824 (5) | C25—C26 | 1.372 (9) |
P1—C1 | 1.825 (5) | C2—H2 | 0.9300 |
P1—C15 | 1.841 (5) | C3—H3 | 0.9300 |
O1—C27 | 1.146 (8) | C4—H4 | 0.9300 |
O2—C28 | 1.145 (7) | C5—H5 | 0.9300 |
O3—C29 | 1.144 (7) | C7—H7 | 0.9300 |
N1—C7 | 1.285 (7) | C8—H8B | 0.9700 |
N1—C8 | 1.483 (6) | C8—H8A | 0.9700 |
C1—C6 | 1.418 (7) | C10—H10 | 0.9300 |
C1—C2 | 1.383 (8) | C11—H11 | 0.9300 |
C2—C3 | 1.396 (9) | C12—H12 | 0.9300 |
C3—C4 | 1.383 (9) | C13—H13 | 0.9300 |
C4—C5 | 1.380 (9) | C14—H14 | 0.9300 |
C5—C6 | 1.397 (7) | C16—H16 | 0.9300 |
C6—C7 | 1.467 (6) | C17—H17 | 0.9300 |
C8—C9 | 1.504 (6) | C18—H18 | 0.9300 |
C9—C14 | 1.376 (8) | C19—H19 | 0.9300 |
C9—C10 | 1.363 (9) | C20—H20 | 0.9300 |
C10—C11 | 1.388 (11) | C22—H22 | 0.9300 |
C11—C12 | 1.368 (15) | C23—H23 | 0.9300 |
C12—C13 | 1.337 (13) | C24—H24 | 0.9300 |
C13—C14 | 1.374 (10) | C25—H25 | 0.9300 |
C15—C16 | 1.376 (8) | C26—H26 | 0.9300 |
C15—C20 | 1.368 (8) | C30—H30A | 0.9700 |
C16—C17 | 1.386 (9) | C30—H30B | 0.9700 |
Re1···C14 | 4.048 (6) | C29···C8 | 3.150 (8) |
Re1···H20 | 3.4200 | C29···Cl1 | 3.172 (6) |
Cl1···P1 | 3.4546 (19) | C29···C28 | 2.673 (8) |
Cl1···N1 | 3.164 (4) | C29···C27 | 2.680 (8) |
Cl1···C1 | 3.447 (6) | C29···N1 | 3.009 (7) |
Cl1···C6 | 3.426 (5) | C1···H22 | 2.6200 |
Cl1···C7 | 3.432 (5) | C2···H30Biv | 2.9200 |
Cl1···C27 | 3.179 (6) | C2···H22 | 3.0500 |
Cl1···C29 | 3.172 (6) | C3···H30Biv | 3.0700 |
Cl2···O3i | 3.363 (7) | C5···H8Biii | 3.0900 |
Cl3···C10ii | 3.554 (9) | C6···H22 | 3.0600 |
Cl1···H20 | 2.8900 | C7···H14 | 3.0200 |
Cl1···H8Aiii | 3.0800 | C11···H3x | 3.0500 |
Cl1···H30Aiv | 3.0400 | C12···H2x | 3.0100 |
Cl1···H7iii | 3.0200 | C15···H2 | 2.6000 |
Cl2···H10i | 2.8900 | C16···H2 | 2.9300 |
Cl2···H14 | 3.0600 | C17···H13iv | 3.0500 |
Cl3···H10ii | 3.0600 | C18···H13iv | 2.7000 |
P1···C7 | 3.247 (5) | C18···H26v | 2.8500 |
P1···C27 | 3.267 (7) | C19···H13iv | 3.0000 |
P1···Cl1 | 3.4546 (19) | C21···H16 | 2.6000 |
P1···N1 | 3.123 (4) | C24···H18x | 2.8700 |
P1···C28 | 3.205 (5) | C26···H16 | 2.7500 |
O2···C13 | 3.412 (9) | C27···H20 | 2.9000 |
O2···C9 | 3.402 (6) | C28···H26 | 2.9500 |
O2···C14 | 3.304 (8) | C29···H22vi | 3.0600 |
O2···C18v | 3.352 (8) | C29···H8B | 2.6200 |
O3···C22vi | 3.327 (8) | C29···H5iii | 2.9700 |
O3···Cl2vi | 3.363 (7) | H2···C15 | 2.6000 |
O3···C5iii | 3.386 (7) | H2···C16 | 2.9300 |
O1···H17v | 2.8200 | H2···C12iv | 3.0100 |
O1···H12vii | 2.8600 | H3···C11iv | 3.0500 |
O2···H18v | 2.6700 | H5···O3iii | 2.7200 |
O2···H23vi | 2.9100 | H5···C29iii | 2.9700 |
O2···H24viii | 2.9200 | H5···H7 | 2.2600 |
O3···H8B | 2.8900 | H7···H8A | 1.9800 |
O3···H22vi | 2.5000 | H7···Cl1iii | 3.0200 |
O3···H5iii | 2.7200 | H7···H5 | 2.2600 |
N1···P1 | 3.123 (4) | H8A···Cl1iii | 3.0800 |
N1···Cl1 | 3.164 (4) | H8A···H7 | 1.9800 |
N1···C1 | 3.184 (6) | H8B···C29 | 2.6200 |
N1···C28 | 3.091 (6) | H8B···O3 | 2.8900 |
N1···C29 | 3.009 (7) | H8B···H10 | 2.3600 |
N1···H14 | 2.6900 | H8B···C5iii | 3.0900 |
C5···O3iii | 3.386 (7) | H10···Cl3ix | 3.0600 |
C6···Cl1 | 3.426 (5) | H10···Cl2vi | 2.8900 |
C7···C14 | 3.552 (7) | H10···H8B | 2.3600 |
C9···O2 | 3.402 (6) | H12···O1xi | 2.8600 |
C9···C28 | 3.135 (7) | H13···C18x | 2.7000 |
C10···Cl3ix | 3.554 (9) | H13···C19x | 3.0000 |
C13···O2 | 3.412 (9) | H13···C17x | 3.0500 |
C14···Re1 | 4.048 (6) | H14···N1 | 2.6900 |
C14···C28 | 3.237 (8) | H14···C7 | 3.0200 |
C14···C7 | 3.552 (7) | H14···Cl2 | 3.0600 |
C14···O2 | 3.304 (8) | H16···C26 | 2.7500 |
C16···C26 | 3.309 (9) | H16···C21 | 2.6000 |
C18···O2v | 3.352 (8) | H17···O1v | 2.8200 |
C20···C27 | 3.342 (9) | H18···O2v | 2.6700 |
C22···O3i | 3.327 (8) | H18···C24iv | 2.8700 |
C26···C28 | 3.373 (8) | H18···H24iv | 2.5200 |
C26···C16 | 3.309 (9) | H20···Re1 | 3.4200 |
C27···P1 | 3.267 (7) | H20···C27 | 2.9000 |
C27···C15 | 3.541 (8) | H20···Cl1 | 2.8900 |
C27···C28 | 2.668 (8) | H22···C1 | 2.6200 |
C27···C20 | 3.342 (9) | H22···C2 | 3.0500 |
C27···Cl1 | 3.179 (6) | H22···O3i | 2.5000 |
C27···C29 | 2.680 (8) | H22···C29i | 3.0600 |
C28···C8 | 3.507 (7) | H22···C6 | 3.0600 |
C28···C14 | 3.237 (8) | H23···O2i | 2.9100 |
C28···P1 | 3.205 (5) | H24···H18x | 2.5200 |
C28···C26 | 3.373 (8) | H24···O2xii | 2.9200 |
C28···C21 | 3.496 (7) | H26···C18v | 2.8500 |
C28···C9 | 3.135 (7) | H26···C28 | 2.9500 |
C28···C27 | 2.668 (8) | H30A···Cl1x | 3.0400 |
C28···C29 | 2.673 (8) | H30B···C2x | 2.9200 |
C28···N1 | 3.091 (6) | H30B···C3x | 3.0700 |
Cl1—Re1—P1 | 88.32 (4) | C23—C24—C25 | 119.6 (6) |
Cl1—Re1—N1 | 84.09 (10) | C24—C25—C26 | 120.7 (6) |
Cl1—Re1—C27 | 90.79 (18) | C21—C26—C25 | 121.0 (6) |
Cl1—Re1—C28 | 177.87 (14) | Re1—C27—O1 | 179.6 (4) |
Cl1—Re1—C29 | 90.18 (18) | Re1—C28—O2 | 175.6 (4) |
P1—Re1—N1 | 83.86 (12) | Re1—C29—O3 | 178.1 (6) |
P1—Re1—C27 | 95.63 (19) | C1—C2—H2 | 119.00 |
P1—Re1—C28 | 93.63 (15) | C3—C2—H2 | 119.00 |
P1—Re1—C29 | 176.34 (16) | C2—C3—H3 | 120.00 |
N1—Re1—C27 | 174.9 (2) | C4—C3—H3 | 120.00 |
N1—Re1—C28 | 96.98 (18) | C3—C4—H4 | 120.00 |
N1—Re1—C29 | 92.66 (19) | C5—C4—H4 | 120.00 |
C27—Re1—C28 | 88.2 (2) | C4—C5—H5 | 119.00 |
C27—Re1—C29 | 87.7 (2) | C6—C5—H5 | 119.00 |
C28—Re1—C29 | 87.9 (2) | N1—C7—H7 | 115.00 |
Re1—P1—C1 | 109.62 (17) | C6—C7—H7 | 115.00 |
Re1—P1—C15 | 117.52 (18) | N1—C8—H8A | 109.00 |
Re1—P1—C21 | 117.93 (15) | N1—C8—H8B | 109.00 |
C1—P1—C15 | 103.3 (2) | C9—C8—H8A | 109.00 |
C1—P1—C21 | 103.7 (2) | C9—C8—H8B | 109.00 |
C15—P1—C21 | 103.0 (2) | H8A—C8—H8B | 108.00 |
Re1—N1—C7 | 128.5 (3) | C9—C10—H10 | 119.00 |
Re1—N1—C8 | 116.7 (3) | C11—C10—H10 | 120.00 |
C7—N1—C8 | 114.5 (4) | C10—C11—H11 | 120.00 |
P1—C1—C2 | 120.9 (4) | C12—C11—H11 | 120.00 |
P1—C1—C6 | 120.4 (4) | C11—C12—H12 | 121.00 |
C2—C1—C6 | 118.7 (5) | C13—C12—H12 | 121.00 |
C1—C2—C3 | 121.9 (5) | C12—C13—H13 | 119.00 |
C2—C3—C4 | 119.5 (6) | C14—C13—H13 | 119.00 |
C3—C4—C5 | 119.4 (6) | C9—C14—H14 | 119.00 |
C4—C5—C6 | 122.2 (5) | C13—C14—H14 | 119.00 |
C1—C6—C5 | 118.4 (4) | C15—C16—H16 | 120.00 |
C1—C6—C7 | 126.9 (4) | C17—C16—H16 | 120.00 |
C5—C6—C7 | 114.7 (4) | C16—C17—H17 | 120.00 |
N1—C7—C6 | 130.7 (4) | C18—C17—H17 | 120.00 |
N1—C8—C9 | 112.4 (4) | C17—C18—H18 | 120.00 |
C8—C9—C10 | 121.0 (5) | C19—C18—H18 | 120.00 |
C8—C9—C14 | 121.7 (5) | C18—C19—H19 | 121.00 |
C10—C9—C14 | 117.2 (5) | C20—C19—H19 | 121.00 |
C9—C10—C11 | 121.0 (7) | C15—C20—H20 | 119.00 |
C10—C11—C12 | 120.6 (9) | C19—C20—H20 | 119.00 |
C11—C12—C13 | 118.4 (8) | C21—C22—H22 | 120.00 |
C12—C13—C14 | 121.7 (8) | C23—C22—H22 | 120.00 |
C9—C14—C13 | 121.1 (6) | C22—C23—H23 | 120.00 |
P1—C15—C16 | 123.0 (4) | C24—C23—H23 | 120.00 |
P1—C15—C20 | 118.1 (4) | C23—C24—H24 | 120.00 |
C16—C15—C20 | 118.9 (5) | C25—C24—H24 | 120.00 |
C15—C16—C17 | 120.0 (6) | C24—C25—H25 | 120.00 |
C16—C17—C18 | 120.2 (7) | C26—C25—H25 | 120.00 |
C17—C18—C19 | 120.8 (7) | C21—C26—H26 | 120.00 |
C18—C19—C20 | 118.5 (7) | C25—C26—H26 | 120.00 |
C15—C20—C19 | 121.6 (6) | Cl2—C30—Cl3 | 110.3 (6) |
P1—C21—C22 | 123.7 (4) | Cl2—C30—H30A | 110.00 |
P1—C21—C26 | 119.0 (4) | Cl2—C30—H30B | 110.00 |
C22—C21—C26 | 117.3 (5) | Cl3—C30—H30A | 110.00 |
C21—C22—C23 | 120.8 (6) | Cl3—C30—H30B | 110.00 |
C22—C23—C24 | 120.7 (6) | H30A—C30—H30B | 108.00 |
Cl1—Re1—P1—C1 | −42.83 (15) | Re1—N1—C7—C6 | 8.8 (8) |
N1—Re1—P1—C1 | 41.41 (18) | C2—C1—C6—C7 | 176.7 (5) |
C27—Re1—P1—C1 | −133.5 (2) | C2—C1—C6—C5 | −0.7 (7) |
C28—Re1—P1—C1 | 138.1 (2) | P1—C1—C2—C3 | 179.5 (5) |
Cl1—Re1—P1—C15 | 74.62 (17) | C6—C1—C2—C3 | 1.2 (8) |
N1—Re1—P1—C15 | 158.86 (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—C4 | 0.3 (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—C6 | 2.9 (9) |
C27—Re1—P1—C21 | 108.2 (3) | C4—C5—C6—C7 | −179.1 (5) |
C28—Re1—P1—C21 | 19.7 (2) | C4—C5—C6—C1 | −1.3 (8) |
Cl1—Re1—N1—C7 | 53.1 (4) | C5—C6—C7—N1 | −161.0 (5) |
P1—Re1—N1—C7 | −35.9 (4) | C1—C6—C7—N1 | 21.6 (8) |
C28—Re1—N1—C7 | −128.8 (4) | N1—C8—C9—C10 | 139.8 (6) |
C29—Re1—N1—C7 | 143.0 (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—C8 | 150.1 (3) | C8—C9—C10—C11 | 177.3 (7) |
C28—Re1—N1—C8 | 57.2 (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—C2 | 147.4 (4) | C9—C10—C11—C12 | 2.2 (14) |
C15—P1—C1—C2 | 21.4 (5) | C10—C11—C12—C13 | −2.2 (15) |
C21—P1—C1—C2 | −85.8 (5) | C11—C12—C13—C14 | 0.9 (14) |
Re1—P1—C1—C6 | −34.3 (4) | C12—C13—C14—C9 | 0.7 (12) |
C15—P1—C1—C6 | −160.4 (4) | P1—C15—C16—C17 | 179.0 (5) |
C21—P1—C1—C6 | 92.5 (4) | C16—C15—C20—C19 | 1.0 (9) |
C1—P1—C15—C20 | 80.7 (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—C22 | 118.7 (4) | C16—C17—C18—C19 | −0.3 (12) |
C1—P1—C21—C22 | −2.7 (5) | C17—C18—C19—C20 | 1.0 (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—C23 | 175.2 (5) |
C1—P1—C21—C26 | 174.7 (4) | C26—C21—C22—C23 | −2.2 (8) |
C15—P1—C21—C26 | 67.3 (4) | P1—C21—C26—C25 | −175.3 (5) |
C21—P1—C15—C16 | 9.2 (5) | C22—C21—C26—C25 | 2.2 (8) |
Re1—P1—C15—C16 | 140.6 (4) | C21—C22—C23—C24 | 1.0 (10) |
C1—P1—C15—C16 | −98.6 (5) | C22—C23—C24—C25 | 0.3 (10) |
C7—N1—C8—C9 | 114.7 (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O3i | 0.93 | 2.50 | 3.327 (8) | 149 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [ReCl(C26H22NP)(CO)3]·CH2Cl2 |
Mr | 770.03 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 16.1971 (12), 9.1981 (6), 20.7977 (17) |
β (°) | 104.820 (9) |
V (Å3) | 2995.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.41 |
Crystal size (mm) | 0.26 × 0.24 × 0.18 |
Data collection | |
Diffractometer | Stoe IPDS diffractometer |
Absorption correction | Analytical from crystal shape (IPDS; Stoe & Cie, 1998) |
Tmin, Tmax | 0.431, 0.612 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27893, 5789, 4647 |
Rint | 0.090 |
(sin θ/λ)max (Å−1) | 0.615 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.081, 0.99 |
No. of reflections | 5789 |
No. of parameters | 355 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.27, −0.56 |
Computer programs: IPDS (Stoe & Cie, 1998), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O3i | 0.9300 | 2.5000 | 3.327 (8) | 149.00 |
Symmetry code: (i) x, y−1, z. |
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Chen, X., Femia, F. J., Babich, J. W. & Zubieta, J. (2001). Inorg. Chim. Acta, 315, 147–152. Web of Science CSD CrossRef CAS Google Scholar
Schultz, T., Schmees, N. & Pfaltz, A. (2004). Appl. Organomet. Chem. 18, 595–601. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1998). IPDS. Version 2.89. Stoe & Cie, Darmstadt, Germany. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).