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Acta Cryst. (2000). C56, 930-931
https://doi.org/10.1107/S0108270100006983
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[1,3-Bis(di­phenyl­phosphino)prop­ane]­tri­chloro­oxorhenium(V)

L. Suescun, A. W. Mombrú, R. A. Mariezcurrena, H. Pardo, S. Russi, C. Kremer, M. Rivero and E. Kremer
Tri­chloro­oxo­[1,3-prop­ane­diyl­bis­(di­phenyl­phosphine)-P,P']rhen­ium(V), [Re­Cl3­O­(C27­H26P2)], crystallizes with four formula units per unit cell. The crystal structure consists of neutral complexes of [ReOCl3(dppp)] [dppp is 1,3-bis(diphenylphosphino)propane] packed by H...[pi]-ring interactions. The Re atom is octahedrally coordinated to the oxo anion, three Cl atoms and two P atoms from the dppp ligand. The six-membered ring formed by the bidentate dppp ligand and the rhenium metal centre is in a chair conformation. The title compound is an intermediate in the synthesis of bis(dppp) complexes of rhenium.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006983/os1104sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006983/os1104Isup2.hkl
Contains datablock I

CCDC reference: 150310

Comment top

Tertiary phosphine ligands have a strong stabilizing effect on rhenium complexes in most oxidation states. [ReI(dppm)3]I [dppm = bis(diphenylphosphinomethane)] (Rivero et al., 1999) and [ReVO2(dppe)2]I [dppe = 1,2-bis(diphenylphosphino)ethane)] (Kremer et al., 1999) can be cited as good examples. The stability of such complexes has been exploited in two ways. Firstly, rhenium complexes are widely used as non radioactive models for technetium equivalents used in nuclear medicine. Secondly, rhenium itself (186/188Re) also has potential in radiotherapy. In the course of our investigation on ReV compounds with diphosphines, we have prepared and characterized by single-crystal X-ray diffraction the mixed-ligand neutral complex [ReVOCl3(dppp)], (I), [dppp = 1,3-bis(diphenylphosphino)propane)], analogous to [ReVOCl3(dppe)] (Sergienko, 1994), (II), and [ReVOCl3(dppm)] (Rossi et al., 1993), (III), starting from ReCl5. \sch

The compounds (I), (II) and (III) share the ReOCl3P2 coordination polyhedra with the ring conformation changing as the Re—P—CnP– ring grows from n = 1 (in III) to n = 3 (in I). The conformation of the ring causes severe distortions in (III) due to the rigidity of the four-membered ring formed whereas there is no cause of distortion in (I) due to the flexibility of the six-membered ring formed. The three compounds pack in the centrosymmetric space group P21/c, but reported in different settings, P21/a, (I), P21/n, (II) and P21/c, (III).

The coordination around the Re metal centre is a distorted octahedron as in (II) and (III). Compound (I) shows an approximate Cs symmetry with the Re1, O1, Cl1 and C2 atoms located at the pseudo-mirror plane. This feature is also observed in the other odd n members of this series (III). The equatorial plane of the octahedron is formed by both P atoms from dppp and two Cl atoms (Cl2 and Cl3). The apical positions are occupied by the oxygen (O1) and the third chlorine (Cl1) atom. The short Re1—O1 distance [1.671 (2) Å] indicates the presence of a triple bond, as in (II) and (III) with distances of 1.679 (5) and 1.671 (6) Å, respectively. The high electron density located in the Re1≡ O1 region forces the negatively charged Cl atoms, located cis to the O1 atom, to be pushed away from the O1 atom. This effect is not observed for the neutral P atoms. The O1—Re1—P angles have values of 90.80 (9) (P1) and 89.33 (9)° (P2) while the O1—Re1—Cl angles are 100.54 (9) (Cl2) and 101.04 (10)° (Cl3). The same effect is observed in (II) and (III), although the chelate rings here are five and four, respectively. The O—Re—P angles are 84.3 (2) and 91.4 (2)° in (II) and 88.7 (3) and 91.3 (3)° in (III) while the O—Re—Cl angles are 103.9 (2) and 101.4 (2)° in (II) and 105.1 (2) and 102.7 (2)° in (III). The Re atom of (I) is displaced 0.2246 (5) Å from the equatorial mean plane towards the O1 atom. The three Cl—Re—Cl angles are expected to be approximately constant within the different complexes and near to the ideal value of 90°. This is observed in (I) where the Cl—Re—Cl angles are 89.37 (3), 87.55 (4) and 86.03 (4) ° for Cl1—Re1—Cl2, Cl1—Re1—Cl3 and Cl2—Re1—Cl3, repsectively. The corresponding Cl—Re—Cl angles are 87.73 (8), 91.50 (8) and 86.32 (10)° in (II) and 89.1 (1), 87.7 (1) and 86.3 (1)° in (III). The P1—Re1—P2 angle is mainly affected by the size of the Re—P—Cn—P ring. This angle increases from 69.2 (1)° in (III) to 91.27 (3)° in (I) while in (II) the angle takes the intermediate value 83.29 (8)°. The O1—Re—Cl1 angle deviates significantly from linearity due to the influence of the Re1≡O1 bond and the consequent shift of the equatorial Cl atoms from the ideal location. This angle is 167.23 (9) in (I), 163.0 (2) in (II) and 162.8 (1)° in (III). The Re1—Cl1 bond distance is 2.4611 (9) Å, while the Re1—Cl2 and Re1—Cl3 bond distances are 2.3639 (10) and 2.3772 (10) Å, respectively. This difference in distances is ascribed to the trans influence suffered by the Cl1 atom. This is also observed in (II) and (III) where the equivalent bond distances are 2.4291 (15), 2.380 (3) and 2.377 (3) Å for (II) and 2.452 (3), 2.365 (4) and 2.373 (3) Å for (III). Finally, the Re—P bond distances show no systematic trend related to the P—Re—Cn—P ring size. The values are 2.4578 (10) and 2.4777 (9) Å in (I), 2.463 (2) Å and 2.445 (2) Å in (II) and 2.439 (3) and 2.449 (2) Å in (III), for Re1—P1 and Re1—P2, respectively.

The six-membered ring formed by Re1—P1—C1—C2—C3—P2 is in a chair conformation in (I) as can be clearly observed by the shifts of the Re1 and C2 atoms from the P1—C1—P2—C3 mean plane [0.840 (3) for Re1 and -0.736 (5) Å for C2]. This conformation is ase expected for complexes containing only one dppp ligand but other conformations were observed in [ReVO2(dppp)2]+ complexes like [ReO2(dppp)2]I·H2O·CH4O (Suescun et al., 1999) while the compound [ReO(OCH3)(dppp)Cl2]·C2H6O (Kremer et al., 1999) contains a single dppp ligand in a chair conformation. The phenyl rings bonded to P1 form a dihedral angle of 77.07 (12)° and those bonded to P2 82.05 (12)°. Similar values were observed for the equivalent angles between adjacent phenyl rings in dppp complexes (Kremer et al., 1999; Suescun et al., 1999). The packing of the structure is directed by H···π-ring interactions forming a three-dimensional network. The main C—H···π-ring interactions are: C2—H2B···(C41→ C46)-ringi, with a perpendicular H···ring distance of 2.961 Å, a C—H···ring-centroid angle of 163.63° and a C···ring-centroid distance of 3.950 Å; C25—H25···(C11→ C6)-ringiiCg(2) with the respective parameters 3.157 Å, 129.76 ° and 4.015 Å; C26—H26···(C11→ C16)-ringii with parameters 2.960 Å, 130.02° and 4.013 Å and C35—H35···(C11→ C16)-ringiii 2.726 Å, 163.58° and 3.645 Å [symmetry operations: (i) -1/2 + x, 3/2 - y, -z; (ii) -x, 2 - y, -z; (iii) 1/2 + x, 3/2 - y, z].

Experimental top

dppp (0.97 g, 2.35 mmol) was dissolved in dry methanol (20 ml). ReCl5 (0.51 g, 1.40 mmol) was added and the mixture was refluxed for 1 h. Then, dichloromethane (5 ml) was added and the suspension was refluxed for 10 h. A green solid was obtained and filtered off from a brown solution. (yield 25–30%). The solid was recrystallized from a mixture of dichloromethane and methanol (10:3, v:v). Analysis calculated for C27H26Cl3OP2Re: C 45.0, H 3.6°. Found: C 45.2, H 3.6%. (Analysis performed with a Carlo Erba model 1108 Elemental Analyser). The presence of the Re≡O bond was confirmed by the IR stretching frequency of 998 cm-1, consistent with the one observed in (III) (Rossi et al., 1993) µ (Re≡O) 990 cm -1.

Structure description top

Tertiary phosphine ligands have a strong stabilizing effect on rhenium complexes in most oxidation states. [ReI(dppm)3]I [dppm = bis(diphenylphosphinomethane)] (Rivero et al., 1999) and [ReVO2(dppe)2]I [dppe = 1,2-bis(diphenylphosphino)ethane)] (Kremer et al., 1999) can be cited as good examples. The stability of such complexes has been exploited in two ways. Firstly, rhenium complexes are widely used as non radioactive models for technetium equivalents used in nuclear medicine. Secondly, rhenium itself (186/188Re) also has potential in radiotherapy. In the course of our investigation on ReV compounds with diphosphines, we have prepared and characterized by single-crystal X-ray diffraction the mixed-ligand neutral complex [ReVOCl3(dppp)], (I), [dppp = 1,3-bis(diphenylphosphino)propane)], analogous to [ReVOCl3(dppe)] (Sergienko, 1994), (II), and [ReVOCl3(dppm)] (Rossi et al., 1993), (III), starting from ReCl5. \sch

The compounds (I), (II) and (III) share the ReOCl3P2 coordination polyhedra with the ring conformation changing as the Re—P—CnP– ring grows from n = 1 (in III) to n = 3 (in I). The conformation of the ring causes severe distortions in (III) due to the rigidity of the four-membered ring formed whereas there is no cause of distortion in (I) due to the flexibility of the six-membered ring formed. The three compounds pack in the centrosymmetric space group P21/c, but reported in different settings, P21/a, (I), P21/n, (II) and P21/c, (III).

The coordination around the Re metal centre is a distorted octahedron as in (II) and (III). Compound (I) shows an approximate Cs symmetry with the Re1, O1, Cl1 and C2 atoms located at the pseudo-mirror plane. This feature is also observed in the other odd n members of this series (III). The equatorial plane of the octahedron is formed by both P atoms from dppp and two Cl atoms (Cl2 and Cl3). The apical positions are occupied by the oxygen (O1) and the third chlorine (Cl1) atom. The short Re1—O1 distance [1.671 (2) Å] indicates the presence of a triple bond, as in (II) and (III) with distances of 1.679 (5) and 1.671 (6) Å, respectively. The high electron density located in the Re1≡ O1 region forces the negatively charged Cl atoms, located cis to the O1 atom, to be pushed away from the O1 atom. This effect is not observed for the neutral P atoms. The O1—Re1—P angles have values of 90.80 (9) (P1) and 89.33 (9)° (P2) while the O1—Re1—Cl angles are 100.54 (9) (Cl2) and 101.04 (10)° (Cl3). The same effect is observed in (II) and (III), although the chelate rings here are five and four, respectively. The O—Re—P angles are 84.3 (2) and 91.4 (2)° in (II) and 88.7 (3) and 91.3 (3)° in (III) while the O—Re—Cl angles are 103.9 (2) and 101.4 (2)° in (II) and 105.1 (2) and 102.7 (2)° in (III). The Re atom of (I) is displaced 0.2246 (5) Å from the equatorial mean plane towards the O1 atom. The three Cl—Re—Cl angles are expected to be approximately constant within the different complexes and near to the ideal value of 90°. This is observed in (I) where the Cl—Re—Cl angles are 89.37 (3), 87.55 (4) and 86.03 (4) ° for Cl1—Re1—Cl2, Cl1—Re1—Cl3 and Cl2—Re1—Cl3, repsectively. The corresponding Cl—Re—Cl angles are 87.73 (8), 91.50 (8) and 86.32 (10)° in (II) and 89.1 (1), 87.7 (1) and 86.3 (1)° in (III). The P1—Re1—P2 angle is mainly affected by the size of the Re—P—Cn—P ring. This angle increases from 69.2 (1)° in (III) to 91.27 (3)° in (I) while in (II) the angle takes the intermediate value 83.29 (8)°. The O1—Re—Cl1 angle deviates significantly from linearity due to the influence of the Re1≡O1 bond and the consequent shift of the equatorial Cl atoms from the ideal location. This angle is 167.23 (9) in (I), 163.0 (2) in (II) and 162.8 (1)° in (III). The Re1—Cl1 bond distance is 2.4611 (9) Å, while the Re1—Cl2 and Re1—Cl3 bond distances are 2.3639 (10) and 2.3772 (10) Å, respectively. This difference in distances is ascribed to the trans influence suffered by the Cl1 atom. This is also observed in (II) and (III) where the equivalent bond distances are 2.4291 (15), 2.380 (3) and 2.377 (3) Å for (II) and 2.452 (3), 2.365 (4) and 2.373 (3) Å for (III). Finally, the Re—P bond distances show no systematic trend related to the P—Re—Cn—P ring size. The values are 2.4578 (10) and 2.4777 (9) Å in (I), 2.463 (2) Å and 2.445 (2) Å in (II) and 2.439 (3) and 2.449 (2) Å in (III), for Re1—P1 and Re1—P2, respectively.

The six-membered ring formed by Re1—P1—C1—C2—C3—P2 is in a chair conformation in (I) as can be clearly observed by the shifts of the Re1 and C2 atoms from the P1—C1—P2—C3 mean plane [0.840 (3) for Re1 and -0.736 (5) Å for C2]. This conformation is ase expected for complexes containing only one dppp ligand but other conformations were observed in [ReVO2(dppp)2]+ complexes like [ReO2(dppp)2]I·H2O·CH4O (Suescun et al., 1999) while the compound [ReO(OCH3)(dppp)Cl2]·C2H6O (Kremer et al., 1999) contains a single dppp ligand in a chair conformation. The phenyl rings bonded to P1 form a dihedral angle of 77.07 (12)° and those bonded to P2 82.05 (12)°. Similar values were observed for the equivalent angles between adjacent phenyl rings in dppp complexes (Kremer et al., 1999; Suescun et al., 1999). The packing of the structure is directed by H···π-ring interactions forming a three-dimensional network. The main C—H···π-ring interactions are: C2—H2B···(C41→ C46)-ringi, with a perpendicular H···ring distance of 2.961 Å, a C—H···ring-centroid angle of 163.63° and a C···ring-centroid distance of 3.950 Å; C25—H25···(C11→ C6)-ringiiCg(2) with the respective parameters 3.157 Å, 129.76 ° and 4.015 Å; C26—H26···(C11→ C16)-ringii with parameters 2.960 Å, 130.02° and 4.013 Å and C35—H35···(C11→ C16)-ringiii 2.726 Å, 163.58° and 3.645 Å [symmetry operations: (i) -1/2 + x, 3/2 - y, -z; (ii) -x, 2 - y, -z; (iii) 1/2 + x, 3/2 - y, z].

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: MSC/AFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: PLATON98 (Spek, 1990) and CSD (Allen and Kennard, 1993).

Figures top
[Figure 1] Fig. 1. ZORTEP (Zsolnai & Pritzkow, 1995) drawing showing the title compound. The chair conformation of the six-membered ring is clearly observed. The H atoms were excluded for the sake of clarity. Displacement ellipsoids are drawn at the 50% probability level.
1,3-bis(diphenylphosphino)propanetrichlorooxorhenium(V) top
Crystal data top
[ReCl3O(C27H26P2)]F(000) = 1408
Mr = 720.97Dx = 1.763 Mg m−3
Monoclinic, P21/aMo Kα radiation, λ = 0.71069 Å
a = 16.5579 (19) ÅCell parameters from 24 reflections
b = 10.9208 (13) Åθ = 18.4–19.8°
c = 16.5426 (19) ŵ = 4.91 mm−1
β = 114.748 (8)°T = 293 K
V = 2716.6 (5) Å3Plate, green
Z = 40.35 × 0.20 × 0.05 mm
Data collection top
Rigaku AFC-7S
diffractometer		5069 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
θ/2θ scansh = −1→21
Absorption correction: ψ scan
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993)		k = −1→14
Tmin = 0.279, Tmax = 0.792l = −21→19
7599 measured reflections3 standard reflections every 150 reflections
6247 independent reflections intensity decay: none
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0264P)2 + 0.5301P]
where P = (Fo2 + 2Fc2)/3
6247 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 1.36 e Å−3
0 restraintsΔρmin = −1.17 e Å−3
Crystal data top
[ReCl3O(C27H26P2)]V = 2716.6 (5) Å3
Mr = 720.97Z = 4
Monoclinic, P21/aMo Kα radiation
a = 16.5579 (19) ŵ = 4.91 mm−1
b = 10.9208 (13) ÅT = 293 K
c = 16.5426 (19) Å0.35 × 0.20 × 0.05 mm
β = 114.748 (8)°
Data collection top
Rigaku AFC-7S
diffractometer		5069 reflections with I > 2σ(I)
Absorption correction: ψ scan
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993)		Rint = 0.023
Tmin = 0.279, Tmax = 0.7923 standard reflections every 150 reflections
7599 measured reflections intensity decay: none
6247 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.072H-atom parameters constrained
S = 1.05Δρmax = 1.36 e Å−3
6247 reflectionsΔρmin = −1.17 e Å−3
307 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Least-squares planes mentioned in text (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

APROXIMATE MIRROR PLANE FOR THE Re COORDINATION POLYHEDRA

-10.5323(0.0130)*x + 4.6167(0.0078)*y - 5.2927(0.0133)*z=0.7635(0.0082)

* 0.0133 (0.0010) Re1 * -0.0082 (0.0006) O1 * -0.0058 (0.0005) Cl1 * 0.0008 (0.0001) C2 1.7761 (0.0019) P1 - 1.7521 (0.0020) P2 1.6582 (0.0025) Cl2 - 1.5751 (0.0026) Cl3 1.3024 (0.0046) C1 - 1.3024 (0.0045) C3

Rms deviation of fitted atoms = 0.0083

EQUATORIAL PLANE P1—P2—CL1—CL2

-4.2247(0.0048)*x + 7.4231(0.0025)*y + 12.0979(0.0036)*z=8.9985(0.0021)

* 0.0177 (0.0005) P1 * -0.0172 (0.0005) P2 * -0.0193 (0.0005) Cl2 * 0.0188 (0.0005) Cl3 - 0.2246 (0.0005) Re1 - 1.8812 (0.0024) O1 2.2257 (0.0010) Cl1

Rms deviation of fitted atoms = 0.0183

Re1—P1—C1—C2—C3—P2 RING LS-PLANE

0.2091 (0.0143) x + 9.2112 (0.0047) y + 7.9810 (0.0116) z = 10.1186 (0.0020)

* 0.1621 (0.0010) Re1 * -0.1982 (0.0016) P1 * -0.2280 (0.0015) P2 * 0.2709 (0.0026) C1 * -0.3152 (0.0029) C2 * 0.3083 (0.0024) C3 - 1.4678 (0.0027) O1 2.3859 (0.0010) Cl1 0.9272 (0.0027) Cl2 0.9965 (0.0029) Cl3

Rms deviation of fitted atoms = 0.2534

P1—P2—C1—C3 MEAN PLANE

3.8669(0.0223)*x + 9.8586(0.0039)*y + 3.8106(0.0247)*z=9.7496(0.0038)

* 0.0140 (0.0013) P1 * -0.0139 (0.0013) P2 * -0.0190 (0.0018) C1 * 0.0188 (0.0018) C3 - 0.7361 (0.0050) C2 0.8404 (0.0027) Re1 - 0.6172 (0.0047) O1 2.6708 (0.0011) Cl1 2.0036 (0.0048) Cl2 2.0878 (0.0051) Cl3

Rms deviation of fitted atoms = 0.0166

C11 -> C16 PHENYL RING

14.0576(0.0169)*x + 3.4185(0.0195)*y - 12.2748(0.0227)*z=1.0878(0.0236)

* -0.0012 (0.0030) C11 * -0.0025 (0.0032) C12 * 0.0057 (0.0035) C13 * -0.0053 (0.0036) C14 * 0.0015 (0.0037) C15 * 0.0017 (0.0035) C16 - 0.0612 (0.0060) P1 1.8469 (0.0085) Re1 2.1364 (0.0099) O1 0.9089 (0.0092) Cl1 3.1656 (0.0051) Cl2 3.6393 (0.0110) Cl3

Rms deviation of fitted atoms = 0.0035

C21 -> C26 PHENYL RING

-11.4553(0.0234)*x + 6.3764(0.0169)*y - 1.5908(0.0306)*z=4.8479(0.0117)

* -0.0026 (0.0028) C21 * 0.0044 (0.0033) C22 * -0.0016 (0.0037) C23 * -0.0031 (0.0037) C24 * 0.0049 (0.0034) C25 * -0.0020 (0.0030) C26 0.0103 (0.0058) P1 - 1.7739 (0.0078) Re1 - 2.2481 (0.0063) O1 - 1.1131 (0.0111) Cl1 - 0.1647 (0.0101) Cl2 - 3.2576 (0.0111) Cl3

Rms deviation of fitted atoms = 0.0033

ANGLE BETWEEN ADJACENT PHENYL RINGS ON P1 (with approx. e.s.d.)=77.07(0.12)

C31 -> C36 PHENYL RING

9.9602(0.0260)*x - 1.6394(0.0209)*y + 7.6218(0.0287)*z=3.8103(0.0121)

* -0.0028 (0.0030) C31 * 0.0044 (0.0034) C32 * -0.0021 (0.0038) C33 * -0.0017 (0.0038) C34 * 0.0033 (0.0036) C35 * -0.0010 (0.0032) C36 0.1301 (0.0061) P2 - 1.4528 (0.0085) Re1 - 1.9321 (0.0069) O1 - 0.7465 (0.0118) Cl1 - 2.8048 (0.0120) Cl2 0.2976 (0.0107) Cl3

Rms deviation of fitted atoms = 0.0028

C41 -> C46 PHENYL RING

-11.7212(0.0211)*x - 1.2524(0.0222)*y + 15.3727(0.0112)*z=1.8692(0.0227)

* -0.0065 (0.0030) C41 * 0.0019 (0.0033) C42 * 0.0032 (0.0036) C43 * -0.0038 (0.0036) C44 * -0.0009 (0.0036) C45 * 0.0061 (0.0033) C46 - 0.0217 (0.0059) P2 - 1.6332 (0.0083) Re1 - 2.4220 (0.0093) O1 - 0.0205 (0.0092) Cl1 - 2.9669 (0.0115) Cl2 - 2.8305 (0.0059) Cl3

Rms deviation of fitted atoms = 0.0043

ANGLE BETWEEN ADJACENT PHENYL RINGS ON P2 (with approx. e.s.d.)=82.05(0.12)

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.

The structure was solved by direct methods, all non hydrogen atoms being located in the initial electronic map. The model was refined by full-matrix least squares placing all H atoms in suitable geometrical positions (0.93 Å for aromatic carbon C—H distance and 0.97 Å for secondary carbon C—H distance) and allowing them to ride with Uiso=1.2Ueq of the parent atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Re10.20032 (1)0.90224 (1)0.24160 (1)0.03125 (5)
O10.18728 (18)0.7868 (2)0.17093 (16)0.0406 (6)
P10.04244 (6)0.89132 (8)0.21319 (6)0.03355 (19)
C11−0.0257 (2)1.0277 (3)0.1683 (2)0.0384 (8)
C12−0.0973 (3)1.0251 (4)0.0856 (3)0.0485 (10)
H12−0.10990.95380.05190.058*
C13−0.1505 (3)1.1277 (5)0.0527 (3)0.0586 (12)
H13−0.19781.1253−0.00330.070*
C14−0.1332 (3)1.2325 (4)0.1025 (3)0.0617 (12)
H14−0.16961.30060.08070.074*
C15−0.0626 (3)1.2375 (4)0.1842 (4)0.0631 (13)
H15−0.05061.30920.21750.076*
C16−0.0089 (3)1.1353 (4)0.2172 (3)0.0546 (11)
H160.03891.13900.27280.066*
C21−0.0117 (2)0.7718 (3)0.1319 (2)0.0386 (8)
C22−0.0638 (3)0.6829 (4)0.1468 (3)0.0517 (10)
H22−0.07160.68340.19930.062*
C23−0.1042 (4)0.5935 (4)0.0833 (4)0.0678 (15)
H23−0.13870.53370.09370.081*
C24−0.0940 (4)0.5922 (4)0.0050 (4)0.0673 (15)
H24−0.12130.5315−0.03710.081*
C25−0.0433 (3)0.6805 (5)−0.0108 (3)0.0586 (12)
H25−0.03700.6802−0.06410.070*
C26−0.0015 (3)0.7703 (4)0.0525 (2)0.0450 (9)
H260.03320.82940.04180.054*
C10.0232 (2)0.8575 (4)0.3115 (2)0.0408 (8)
H1A0.04120.92850.35030.049*
H1B−0.04030.84730.29270.049*
C20.0699 (3)0.7452 (4)0.3664 (3)0.0422 (8)
H2A0.06180.67720.32600.051*
H2B0.04070.72370.40450.051*
C30.1704 (2)0.7596 (3)0.4253 (2)0.0379 (8)
H3A0.18890.69570.47010.045*
H3B0.18020.83770.45590.045*
P20.24034 (6)0.75229 (8)0.36472 (6)0.03208 (18)
C310.2319 (3)0.5955 (3)0.3246 (2)0.0378 (8)
C320.1945 (3)0.5023 (4)0.3544 (3)0.0520 (10)
H320.16870.52040.39330.062*
C330.1950 (4)0.3832 (4)0.3272 (4)0.0702 (15)
H330.16910.32170.34720.084*
C340.2340 (4)0.3551 (4)0.2703 (3)0.0702 (15)
H340.23440.27460.25210.084*
C350.2726 (4)0.4467 (5)0.2402 (3)0.0622 (13)
H350.29920.42790.20220.075*
C360.2712 (3)0.5657 (4)0.2671 (3)0.0471 (9)
H360.29680.62720.24660.057*
C410.3537 (2)0.7592 (3)0.4527 (2)0.0374 (8)
C420.4039 (3)0.6545 (4)0.4830 (3)0.0529 (11)
H420.38000.57890.45890.063*
C430.4907 (3)0.6613 (5)0.5498 (3)0.0628 (12)
H430.52410.59020.56990.075*
C440.5266 (3)0.7727 (5)0.5858 (3)0.0594 (12)
H440.58440.77740.62980.071*
C450.4767 (3)0.8763 (4)0.5564 (3)0.0580 (12)
H450.50070.95180.58070.070*
C460.3902 (3)0.8702 (4)0.4904 (3)0.0515 (10)
H460.35680.94140.47160.062*
Cl10.20336 (7)1.04090 (8)0.36012 (6)0.0416 (2)
Cl20.16743 (8)1.07104 (9)0.14351 (7)0.0506 (2)
Cl30.35222 (7)0.95293 (11)0.28366 (7)0.0531 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.03432 (8)0.03126 (8)0.02587 (8)−0.00311 (5)0.01035 (6)−0.00256 (5)
O10.0474 (15)0.0398 (13)0.0307 (12)0.0013 (12)0.0126 (11)−0.0069 (11)
P10.0348 (5)0.0335 (4)0.0297 (4)0.0009 (4)0.0110 (4)0.0008 (3)
C110.0365 (19)0.0362 (18)0.0397 (19)0.0061 (15)0.0131 (16)0.0032 (15)
C120.049 (2)0.054 (2)0.037 (2)0.0144 (19)0.0127 (18)0.0032 (18)
C130.052 (3)0.069 (3)0.046 (2)0.014 (2)0.011 (2)0.012 (2)
C140.058 (3)0.052 (3)0.073 (3)0.019 (2)0.025 (2)0.021 (2)
C150.066 (3)0.041 (2)0.072 (3)0.007 (2)0.019 (3)0.000 (2)
C160.057 (3)0.042 (2)0.051 (2)0.008 (2)0.009 (2)−0.0009 (19)
C210.0364 (18)0.0395 (19)0.0334 (18)−0.0018 (15)0.0082 (15)−0.0012 (15)
C220.051 (2)0.051 (2)0.045 (2)−0.015 (2)0.0109 (19)0.0009 (18)
C230.062 (3)0.056 (3)0.067 (3)−0.025 (2)0.009 (3)0.001 (2)
C240.067 (3)0.050 (3)0.059 (3)−0.009 (2)0.000 (3)−0.016 (2)
C250.056 (3)0.069 (3)0.041 (2)−0.001 (2)0.011 (2)−0.015 (2)
C260.042 (2)0.051 (2)0.0375 (19)−0.0050 (18)0.0129 (17)−0.0015 (17)
C10.0361 (19)0.051 (2)0.0374 (19)0.0061 (17)0.0173 (16)0.0042 (17)
C20.042 (2)0.047 (2)0.040 (2)−0.0009 (17)0.0193 (17)0.0069 (16)
C30.048 (2)0.0403 (18)0.0269 (16)0.0016 (16)0.0170 (16)0.0022 (14)
P20.0330 (4)0.0304 (4)0.0290 (4)−0.0002 (3)0.0092 (4)−0.0014 (3)
C310.040 (2)0.0317 (17)0.0351 (19)−0.0012 (14)0.0097 (16)−0.0043 (13)
C320.057 (3)0.038 (2)0.061 (3)−0.0016 (19)0.024 (2)0.0033 (19)
C330.077 (4)0.036 (2)0.090 (4)−0.009 (2)0.028 (3)−0.002 (2)
C340.084 (4)0.037 (2)0.069 (3)0.008 (2)0.011 (3)−0.020 (2)
C350.074 (3)0.055 (3)0.053 (3)0.015 (3)0.022 (2)−0.011 (2)
C360.048 (2)0.043 (2)0.050 (2)0.0038 (19)0.021 (2)−0.0036 (18)
C410.0343 (18)0.045 (2)0.0282 (16)0.0000 (15)0.0087 (14)0.0027 (14)
C420.048 (2)0.041 (2)0.052 (2)−0.0007 (18)0.004 (2)0.0043 (18)
C430.052 (3)0.061 (3)0.054 (3)0.010 (2)0.002 (2)0.012 (2)
C440.038 (2)0.077 (3)0.044 (2)−0.004 (2)−0.0022 (18)0.004 (2)
C450.055 (3)0.058 (3)0.044 (2)−0.008 (2)0.004 (2)−0.008 (2)
C460.050 (2)0.046 (2)0.042 (2)0.0054 (19)0.0034 (19)−0.0081 (18)
Cl10.0500 (5)0.0362 (4)0.0341 (4)0.0017 (4)0.0132 (4)−0.0070 (3)
Cl20.0693 (7)0.0395 (5)0.0371 (5)−0.0063 (5)0.0167 (5)0.0061 (4)
Cl30.0390 (5)0.0708 (7)0.0494 (6)−0.0146 (5)0.0185 (5)−0.0113 (5)
Geometric parameters (Å, º) top
Re1—O11.671 (2)C24—C251.375 (7)
Re1—Cl22.3639 (10)C25—C261.389 (6)
Re1—Cl32.3772 (10)C1—C21.530 (5)
Re1—P12.4578 (10)C2—C31.544 (5)
Re1—Cl12.4611 (9)C3—P21.823 (4)
Re1—P22.4777 (9)P2—C311.821 (3)
P1—C211.818 (4)P2—C411.833 (4)
P1—C11.820 (4)C31—C321.385 (5)
P1—C111.828 (4)C31—C361.397 (6)
C11—C121.385 (5)C32—C331.377 (6)
C11—C161.388 (6)C33—C341.381 (8)
C12—C131.388 (6)C34—C351.387 (8)
C13—C141.368 (7)C35—C361.377 (6)
C14—C151.369 (7)C41—C421.378 (5)
C15—C161.388 (6)C41—C461.382 (5)
C21—C221.389 (5)C42—C431.401 (6)
C21—C261.393 (5)C43—C441.376 (7)
C22—C231.384 (6)C44—C451.365 (6)
C23—C241.375 (8)C45—C461.392 (6)
O1—Re1—Cl2100.54 (9)C26—C21—P1119.3 (3)
O1—Re1—Cl3101.04 (10)C23—C22—C21119.8 (4)
Cl2—Re1—Cl386.03 (4)C24—C23—C22120.8 (4)
O1—Re1—P190.80 (9)C25—C24—C23119.9 (4)
Cl2—Re1—P189.17 (4)C24—C25—C26120.2 (4)
Cl3—Re1—P1167.85 (4)C25—C26—C21120.1 (4)
O1—Re1—Cl1167.23 (9)C2—C1—P1117.3 (3)
Cl2—Re1—Cl189.37 (3)C1—C2—C3115.9 (3)
Cl3—Re1—Cl187.55 (4)C2—C3—P2114.4 (2)
P1—Re1—Cl181.23 (3)C31—P2—C3105.80 (18)
O1—Re1—P289.33 (9)C31—P2—C41102.99 (18)
Cl2—Re1—P2170.11 (3)C3—P2—C41103.69 (17)
Cl3—Re1—P291.56 (4)C31—P2—Re1111.63 (12)
P1—Re1—P291.27 (3)C3—P2—Re1114.21 (12)
Cl1—Re1—P280.94 (3)C41—P2—Re1117.28 (12)
C21—P1—C1107.39 (18)C32—C31—C36118.5 (3)
C21—P1—C11104.77 (17)C32—C31—P2122.6 (3)
C1—P1—C11102.68 (17)C36—C31—P2118.7 (3)
C21—P1—Re1109.36 (13)C33—C32—C31120.8 (5)
C1—P1—Re1114.12 (13)C32—C33—C34120.1 (5)
C11—P1—Re1117.66 (13)C33—C34—C35120.1 (4)
C12—C11—C16118.3 (4)C36—C35—C34119.5 (5)
C12—C11—P1120.8 (3)C35—C36—C31121.1 (4)
C16—C11—P1120.9 (3)C42—C41—C46118.7 (3)
C11—C12—C13120.7 (4)C42—C41—P2121.1 (3)
C14—C13—C12120.0 (4)C46—C41—P2120.2 (3)
C13—C14—C15120.3 (4)C41—C42—C43120.4 (4)
C14—C15—C16119.9 (4)C44—C43—C42120.2 (4)
C11—C16—C15120.8 (4)C45—C44—C43119.4 (4)
C22—C21—C26119.3 (4)C44—C45—C46120.7 (4)
C22—C21—P1121.4 (3)C41—C46—C45120.6 (4)
O1—Re1—P1—C21−1.00 (15)C1—C2—C3—P2−76.4 (4)
Cl2—Re1—P1—C2199.53 (13)C2—C3—P2—C31−67.4 (3)
Cl3—Re1—P1—C21166.23 (19)C2—C3—P2—C41−175.4 (3)
Cl1—Re1—P1—C21−170.98 (13)C2—C3—P2—Re155.8 (3)
P2—Re1—P1—C21−90.35 (13)O1—Re1—P2—C31−3.05 (17)
O1—Re1—P1—C1119.29 (17)Cl2—Re1—P2—C31−180 (13)
Cl2—Re1—P1—C1−140.17 (15)Cl3—Re1—P2—C31−104.08 (15)
Cl3—Re1—P1—C1−73.5 (2)P1—Re1—P2—C3187.74 (14)
Cl1—Re1—P1—C1−50.68 (15)Cl1—Re1—P2—C31168.65 (15)
P2—Re1—P1—C129.95 (15)O1—Re1—P2—C3−123.01 (16)
O1—Re1—P1—C11−120.30 (17)Cl2—Re1—P2—C360.2 (3)
Cl2—Re1—P1—C11−19.76 (14)Cl3—Re1—P2—C3135.96 (14)
Cl3—Re1—P1—C1146.9 (2)P1—Re1—P2—C3−32.22 (13)
Cl1—Re1—P1—C1169.73 (14)Cl1—Re1—P2—C348.69 (13)
P2—Re1—P1—C11150.36 (14)O1—Re1—P2—C41115.41 (16)
C21—P1—C11—C12−3.9 (4)Cl2—Re1—P2—C41−61.3 (3)
C1—P1—C11—C12−116.0 (4)Cl3—Re1—P2—C4114.38 (14)
Re1—P1—C11—C12117.8 (3)P1—Re1—P2—C41−153.81 (14)
C21—P1—C11—C16173.9 (4)Cl1—Re1—P2—C41−72.89 (14)
C1—P1—C11—C1661.8 (4)C3—P2—C31—C32−12.3 (4)
Re1—P1—C11—C16−64.4 (4)C41—P2—C31—C3296.2 (4)
C16—C11—C12—C130.3 (7)Re1—P2—C31—C32−137.1 (3)
P1—C11—C12—C13178.2 (4)C3—P2—C31—C36173.1 (3)
C11—C12—C13—C14−1.0 (7)C41—P2—C31—C36−78.4 (3)
C12—C13—C14—C151.3 (8)Re1—P2—C31—C3648.3 (3)
C13—C14—C15—C16−0.9 (8)C36—C31—C32—C33−0.7 (7)
C12—C11—C16—C150.1 (7)P2—C31—C32—C33−175.3 (4)
P1—C11—C16—C15−177.8 (4)C31—C32—C33—C340.7 (8)
C14—C15—C16—C110.2 (8)C32—C33—C34—C35−0.1 (8)
C1—P1—C21—C225.7 (4)C33—C34—C35—C36−0.4 (8)
C11—P1—C21—C22−103.0 (4)C34—C35—C36—C310.4 (7)
Re1—P1—C21—C22130.1 (3)C32—C31—C36—C350.2 (6)
C1—P1—C21—C26−175.1 (3)P2—C31—C36—C35175.0 (4)
C11—P1—C21—C2676.2 (3)C31—P2—C41—C42−10.5 (4)
Re1—P1—C21—C26−50.8 (3)C3—P2—C41—C4299.7 (4)
C26—C21—C22—C230.6 (6)Re1—P2—C41—C42−133.4 (3)
P1—C21—C22—C23179.8 (4)C31—P2—C41—C46170.0 (3)
C21—C22—C23—C24−0.6 (8)C3—P2—C41—C46−79.9 (4)
C22—C23—C24—C25−0.2 (8)Re1—P2—C41—C4647.0 (4)
C23—C24—C25—C260.8 (8)C46—C41—C42—C43−0.9 (7)
C24—C25—C26—C21−0.7 (7)P2—C41—C42—C43179.5 (4)
C22—C21—C26—C250.0 (6)C41—C42—C43—C440.0 (7)
P1—C21—C26—C25−179.2 (3)C42—C43—C44—C450.5 (8)
C21—P1—C1—C269.0 (3)C43—C44—C45—C46−0.1 (8)
C11—P1—C1—C2179.2 (3)C42—C41—C46—C451.3 (7)
Re1—P1—C1—C2−52.3 (3)P2—C41—C46—C45−179.1 (4)
P1—C1—C2—C375.3 (4)C44—C45—C46—C41−0.8 (8)

Experimental details

Crystal data
Chemical formula[ReCl3O(C27H26P2)]
Mr720.97
Crystal system, space groupMonoclinic, P21/a
Temperature (K)293
a, b, c (Å)16.5579 (19), 10.9208 (13), 16.5426 (19)
β (°) 114.748 (8)
V (Å3)2716.6 (5)
Z4
Radiation typeMo Kα
µ (mm−1)4.91
Crystal size (mm)0.35 × 0.20 × 0.05
Data collection
DiffractometerRigaku AFC-7S
Absorption correctionψ scan
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993)
Tmin, Tmax0.279, 0.792
No. of measured, independent and
observed [I > 2σ(I)] reflections		7599, 6247, 5069
Rint0.023
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.072, 1.05
No. of reflections6247
No. of parameters307
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.36, −1.17

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1995), PLATON98 (Spek, 1990) and CSD (Allen and Kennard, 1993).

 

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