metal-organic compounds
A dimer of bis(N-heterocyclic carbene)rhodium(I) centres spanned by a dibenzo-18-crown-6 bridge from synchrotron radiation
aSchool of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia, and bMark Wainwright Analytical Centre, University of New South Wales, Sydney, NSW 2052, Australia
*Correspondence e-mail: s.colbran@unsw.edu.au
The compound (μ-3,3′,3′′,3′′′-{[2,5,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosa-1(22),9,11,13,23,25-hexaene-11,12,24,25-tetrayl]tetrakis(methylene)}tetrakis(1-methyl-1H-imidazol-2-yl))bis[(η4-cycloocta-1,4-diene)rhodium(I)] bis(hexafluoridophosphate) acetonitrile sesquisolvate dihydrate, [Rh2(C8H12)2(C40H42N8O6)](PF6)2·1.5CH3CN·2H2O, crystallized from acetonitrile under an atmosphere of diethyl ether. In the the complex cation exhibits two square-planar RhI centres, each bound by a cyclooctadiene (COD) ligand and by two adjacent imidazolylidene N-heterocyclic carbene (NHC) donors from the same phenoxy ring of the {[dibenzo-18-crown-6-11,12,24,25-tetrayl]tetrakis(methylene)}tetrakis(1-methyl-1H-imidazol-2-yl) (L) ligand. The dibenzo-crown ether bridge of L spans the Rh centres and forms hydrogen bonds with water molecules. One water molecule with half occupancy bridges adjacent macrocycles in the lattice. Another water with full occupancy forms weak hydrogen bonds to the crown ether O atoms and is, in turn, part hydrogen bonded by a lattice water with half occupancy. The latter water is within hydrogen-bonding distance of a fourth water also with partial occupancy. The result of these interactions is the formation of a layer in the ab plane. Two PF6− ions, one of which is twofold disordered, and one ordered and one twofold disordered (with 0.5 occupancy) lattice acetonitrile molecules complete the crystal structure.
Related literature
For the related complex [K(L){Rh(COD)}2][PF6]3, which has a potassium ion bound within the crown ether bridge of the ligand L, see: Shrestha et al. (2011). For the well known Rh(I)(NHC)2(COD) centres, see: Mata et al. (2004); Riederer et al. (2010).
Experimental
Crystal data
|
Data collection
|
Refinement
|
Data collection: BLU-ICE (McPhillips et al., 2002); cell XDS (Kabsch, 1993); data reduction: XDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S160053681204901X/tk5170sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681204901X/tk5170Isup2.hkl
The synthesis of [(L){Rh(COD)}2]Br2 (L = bis{4,5-bis(1-methylene-3-methyl- imidazolidene)}benzo-18-crown-6; COD = 1,5-cyclooctadiene) has been described by us (Shrestha et al., 2011). This was dissolved in methanol and treated with aqueous [NH4][PF6]. The yellow-orange precipitate was collected by filtration, and recrystallized from acetonitrile under an atmosphere of diethyl ether to afford very thin yellow crystalline platelets of the title complex, which were used for this X-ray
determination.The
contained one ordered and one orientationally disordered PF6- anions and one ordered and one orientationally disordered acetonitrile (solvent) molecules. In addition, there is one lattice water with full occupancy and there are three water molecules with partial occupancies. All the disorders were modelled keeping the geometries of each entity in question restrained using DFIX / SADI commands and the atomic displacement parameters were restrained using DELU / SIMU commands. The H atoms to the water molecules were fixed so as achieve the best possible O—H···O interactions between them. The low occupancy entities were kept isotropic throughout the refinement.A total of four water molecules have been located in difference Fourier maps, which are at favorable hydrogen bonding distances from each other and other possible H-bonding groups. However, difference Fourier maps did not reveal the H-atoms attached to these waters, probably because of the possible orientational disorder and/or low occupancies of some of the water molecules. One of the possible constellations for water H-atoms is modeled in the present structure using OLEX-2 software (Dolomanov et al., 2009).
Amongst the waters, O1M situated at the centre of the crown has the full occupancy. However, it is almost equidistant from the O atoms O1, O2, O3, O4, O5 and O6 of the crown (distances range from 3.060 – 3.219 Å), all of which are larger than the normally observed O···O distances (2.6 – 2.8 Å). Therefore, this water is likely to be orientationally disordered with H-atoms making weaker O—H···O hydrogen bonds with any of the pairs of crown O-atoms or forming bifurcated interactions. In the present model, the hydrogen atoms H1MA and H1MB make bifurcated O—H···O interactions with oxygen atoms O1, O6 and O2, O3 respectively. Water molecule O1W (occupancy 1/2) at a distance of 2.80 Å from O1M is modeled to make two H-bonding interactions, one with the water O1M (O1W– H1WA···O1M) and the other being the O—H···N contact with the major site of an acetonitrile (O1W—H1WB···N1CN). One of the H-atoms on O1W could also make O—H···O contact with the lowest occupied water molecule O2W (occupancy 1/4), but this would leave the acetonitrile without any (binding) short contact. It could be possible that one of the H-atoms on O2W makes O—H···O contact with the water O1W. However, considering the twofold symmetry about this water, it is preferred that both the H-atoms of O2W make O—H···π contacts with the adjacent imidazolylidene rings with shorter approaches to C2D, C3D on one side and C7D, C8D on the other. As O2W has low occupancy, efforts were not made to optimize the O—H···pi contacts. Water molecule O3W, with a partial occupancy (1/2), exhibits obvious O—H···O bonding: it forms O3W—H3WA···O2 and O3W—H3WB···O5 bridges between adjacent crown ether macrocycles in the crystal lattice.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the
in the riding model approximation, with Uiso(H) = 1.2-1.5Uequiv(C).The sum of the acute C(NHC)-Rh-{C=C(centroid) for COD} bond angles is 360.2° for Rh1 and 359.3° for Rh2 indicative for the planarity of these centres. The Rh–C bond lengths are in the normal range (Mata et al., 2004; Riederer et al., 2010; Shrestha et al., 2011): 2.033 (4) - 2.042 (4) Å for the Rh—C(NHC) and 2.196 (5) - 2.214 (5) Å for the Rh–C(COD) distances. The dibenzo-18-crown-6 bridge adopts an 'umbrella' shape and forms hydrogen bonds with a centrally located water molecule (O1M; see Fig. 2). Other lattice water with partial occupancy are observed in the structure and are depicted in Fig. 2. To use the nomenclature introduced in Shrestha et al. (2011), the Rh(NHC)2(COD) centres are aligned 'up-and-out' for Rh1 and 'down-and-out' for Rh2.
For the related complex [K(L){Rh(COD)}2][PF6]3, which has a potassium ion bound within the crown ether bridge of the ligand L, see: Shrestha et al. (2011). For the well known Rh(I)(NHC)2(COD) centres, see: Mata et al. (2004); Riederer et al. (2010).
Data collection: BLU-ICE (McPhillips et al., 2002); cell
XDS (Kabsch, 1993); data reduction: XDS (Kabsch, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. View of the [(L){Rh(COD)}2]2+ cation showing 50% thermal ellipsoids (H-atoms are omitted for clarity). | |
Fig. 2. Ball-and-stick view showing the packing of [(L){Rh(COD)}2]2+ cations and lattice water molecules in the crystal structure. The labelling scheme adopted for the waters is shown. |
[Rh2(C8H12)2(C40H42N8O6)](PF6)2·1.5C2H3N·2H2O | Z = 2 |
Mr = 1540.55 | F(000) = 1574 |
Triclinic, P1 | Dx = 1.475 Mg m−3 |
Hall symbol: -P 1 | Synchrotron radiation, λ = 0.71073 Å |
a = 10.510 (2) Å | Cell parameters from 9980 reflections |
b = 15.630 (3) Å | θ = 2.5–22.5° |
c = 23.280 (5) Å | µ = 0.61 mm−1 |
α = 104.69 (3)° | T = 100 K |
β = 90.20 (3)° | Plates, yellow |
γ = 109.58 (3)° | 0.03 × 0.02 × 0.01 mm |
V = 3468.9 (12) Å3 |
3-BM1 Australian Synchrotron diffractometer | 9939 reflections with I > 2σ(I) |
Radiation source: Synchrotron BM | Rint = 0.038 |
Si<111> monochromator | θmax = 25.0°, θmin = 1.8° |
Phi Scan scans | h = −12→12 |
43942 measured reflections | k = −18→18 |
11473 independent reflections | l = −27→27 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.33 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.5989P] where P = (Fo2 + 2Fc2)/3 |
11473 reflections | (Δ/σ)max = 0.001 |
964 parameters | Δρmax = 1.15 e Å−3 |
270 restraints | Δρmin = −1.40 e Å−3 |
[Rh2(C8H12)2(C40H42N8O6)](PF6)2·1.5C2H3N·2H2O | γ = 109.58 (3)° |
Mr = 1540.55 | V = 3468.9 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.510 (2) Å | Synchrotron radiation, λ = 0.71073 Å |
b = 15.630 (3) Å | µ = 0.61 mm−1 |
c = 23.280 (5) Å | T = 100 K |
α = 104.69 (3)° | 0.03 × 0.02 × 0.01 mm |
β = 90.20 (3)° |
3-BM1 Australian Synchrotron diffractometer | 9939 reflections with I > 2σ(I) |
43942 measured reflections | Rint = 0.038 |
11473 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 270 restraints |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.33 | Δρmax = 1.15 e Å−3 |
11473 reflections | Δρmin = −1.40 e Å−3 |
964 parameters |
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. |
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 crystal lattice contained one ordered and one orientationally disordered PF6- anions and one ordered and one orientationally disordered acetonitrile (solvent) molecules. In addition, there is one lattice water with full occupancy and there are three water molecules with partial occupancies. All the disorders were modelled keeping the geometries of each entity in question restrained using DFIX / SADI commands and the atomic displacement parameters were restrained using DELU / SIMU commands. The H atoms to the water molecules were fixed so as achieve the best possible O—H···O interactions between them. The low occupancy entities were kept isotropic throughout the refinement. A total of four water molecules have been located in difference Fourier maps, which are at favorable hydrogen bonding distances from each other and other possible H-bonding groups. However, difference Fourier maps did not reveal the H-atoms attached to these waters, most probably because of the possible orientational disorder and/or low occupancies of some of the water molecules. One of the possible constellations for water H-atoms is modeled in the present structure using OLEX-2 v1.2 software (Dolomanov et al., 2009). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Rh1 | 0.60101 (3) | 1.202962 (19) | −0.134418 (12) | 0.02157 (12) | |
C1C | 0.6876 (5) | 1.1042 (3) | −0.1908 (2) | 0.0417 (11) | |
H1C | 0.7331 | 1.1033 | −0.1568 | 0.050* | |
C2C | 0.7299 (5) | 1.1861 (3) | −0.20809 (17) | 0.0353 (10) | |
H2C | 0.8030 | 1.2361 | −0.1854 | 0.042* | |
C3C | 0.6669 (7) | 1.2010 (6) | −0.2608 (3) | 0.074 (2) | |
H3C | 0.7160 | 1.2101 | −0.2933 | 0.089* | |
C4C | 0.5322 (6) | 1.2011 (6) | −0.2610 (3) | 0.074 (2) | |
H4C | 0.4918 | 1.2102 | −0.2935 | 0.089* | |
C5C | 0.4553 (4) | 1.1865 (3) | −0.20789 (17) | 0.0332 (9) | |
H5C | 0.4334 | 1.2367 | −0.1848 | 0.040* | |
C6C | 0.4158 (5) | 1.1050 (3) | −0.1915 (2) | 0.0417 (11) | |
H6C | 0.3685 | 1.1038 | −0.1578 | 0.050* | |
C7C | 0.4411 (7) | 1.0166 (4) | −0.2224 (4) | 0.085 (2) | |
H7C | 0.3691 | 0.9625 | −0.2416 | 0.102* | |
C8C | 0.5743 (7) | 1.0162 (4) | −0.2224 (4) | 0.087 (2) | |
H8C | 0.5918 | 0.9620 | −0.2417 | 0.104* | |
N1B | 0.7968 (3) | 1.2112 (2) | −0.03429 (14) | 0.0281 (7) | |
N2B | 0.8752 (3) | 1.3339 (2) | −0.06641 (14) | 0.0286 (7) | |
N3B | 0.4146 (3) | 1.2115 (2) | −0.03475 (14) | 0.0283 (7) | |
N4B | 0.4581 (3) | 1.3342 (2) | −0.06650 (14) | 0.0281 (7) | |
C1B | 0.7069 (4) | 1.1216 (3) | −0.02549 (18) | 0.0312 (9) | |
H1B1 | 0.7598 | 1.0822 | −0.0227 | 0.037* | |
H1B2 | 0.6399 | 1.0887 | −0.0597 | 0.037* | |
C2B | 0.9229 (4) | 1.2639 (3) | −0.00328 (18) | 0.0341 (10) | |
H2B | 0.9651 | 1.2489 | 0.0260 | 0.041* | |
C3B | 0.9726 (4) | 1.3406 (3) | −0.02344 (18) | 0.0344 (10) | |
H3B | 1.0561 | 1.3888 | −0.0111 | 0.041* | |
C4B | 0.7667 (4) | 1.2541 (3) | −0.07322 (16) | 0.0245 (8) | |
C5B | 0.8905 (5) | 1.4033 (3) | −0.0994 (2) | 0.0378 (10) | |
H5B1 | 0.8084 | 1.3867 | −0.1245 | 0.057* | |
H5B2 | 0.9645 | 1.4049 | −0.1236 | 0.057* | |
H5B3 | 0.9086 | 1.4643 | −0.0720 | 0.057* | |
C6B | 0.4144 (4) | 1.1213 (3) | −0.02577 (18) | 0.0305 (9) | |
H6B1 | 0.4484 | 1.0883 | −0.0598 | 0.037* | |
H6B2 | 0.3221 | 1.0821 | −0.0232 | 0.037* | |
C7B | 0.3685 (4) | 1.3410 (3) | −0.02353 (18) | 0.0349 (10) | |
H7B | 0.3338 | 1.3894 | −0.0110 | 0.042* | |
C8B | 0.3415 (4) | 1.2638 (3) | −0.00349 (18) | 0.0335 (9) | |
H8B | 0.2847 | 1.2487 | 0.0257 | 0.040* | |
C9B | 0.4873 (4) | 1.2543 (3) | −0.07371 (16) | 0.0237 (8) | |
C10B | 0.5125 (5) | 1.4037 (3) | −0.0996 (2) | 0.0380 (10) | |
H10A | 0.5735 | 1.3849 | −0.1263 | 0.057* | |
H10B | 0.5605 | 1.4640 | −0.0722 | 0.057* | |
H10C | 0.4395 | 1.4083 | −0.1221 | 0.057* | |
Rh2 | 0.30618 (4) | 0.61278 (2) | 0.415306 (15) | 0.03863 (14) | |
C1E | 0.3928 (6) | 0.5140 (4) | 0.4374 (3) | 0.0533 (13) | |
H1E | 0.4393 | 0.5146 | 0.4035 | 0.064* | |
C2E | 0.4338 (6) | 0.5957 (4) | 0.4838 (2) | 0.0486 (12) | |
H2E | 0.5062 | 0.6463 | 0.4786 | 0.058* | |
C3E | 0.3717 (8) | 0.6099 (7) | 0.5419 (3) | 0.089 (2) | |
H3E1 | 0.3745 | 0.5607 | 0.5596 | 0.107* | |
H3E2 | 0.4297 | 0.6694 | 0.5682 | 0.107* | |
C4E | 0.2381 (7) | 0.6104 (7) | 0.5416 (3) | 0.089 (2) | |
H4E1 | 0.2407 | 0.6701 | 0.5679 | 0.107* | |
H4E2 | 0.1856 | 0.5614 | 0.5594 | 0.107* | |
C5E | 0.1602 (6) | 0.5968 (4) | 0.4835 (2) | 0.0487 (12) | |
H5E | 0.1369 | 0.6470 | 0.4784 | 0.058* | |
C6E | 0.1207 (5) | 0.5140 (4) | 0.4370 (3) | 0.0515 (13) | |
H6E | 0.0759 | 0.5141 | 0.4025 | 0.062* | |
C7E | 0.1443 (7) | 0.4247 (4) | 0.4377 (4) | 0.094 (3) | |
H7E | 0.0721 | 0.3709 | 0.4387 | 0.113* | |
C8E | 0.2791 (7) | 0.4240 (4) | 0.4370 (5) | 0.096 (3) | |
H8E | 0.2968 | 0.3693 | 0.4364 | 0.115* | |
N1D | 0.5737 (4) | 0.7555 (3) | 0.40038 (16) | 0.0404 (9) | |
N2D | 0.5296 (4) | 0.6290 (3) | 0.32954 (17) | 0.0429 (9) | |
N3D | 0.1805 (4) | 0.7558 (3) | 0.39959 (17) | 0.0397 (9) | |
N4D | 0.0999 (4) | 0.6295 (3) | 0.32853 (17) | 0.0413 (9) | |
C1D | 0.5603 (6) | 0.8278 (3) | 0.45105 (19) | 0.0454 (12) | |
H1D1 | 0.6468 | 0.8593 | 0.4752 | 0.054* | |
H1D2 | 0.4946 | 0.7979 | 0.4755 | 0.054* | |
C2D | 0.6872 (5) | 0.7661 (4) | 0.3674 (2) | 0.0459 (12) | |
H2D | 0.7668 | 0.8183 | 0.3752 | 0.055* | |
C3D | 0.6599 (5) | 0.6878 (4) | 0.3231 (2) | 0.0488 (13) | |
H3D | 0.7157 | 0.6747 | 0.2938 | 0.059* | |
C4D | 0.4766 (4) | 0.6702 (3) | 0.37734 (18) | 0.0355 (10) | |
C5D | 0.4610 (5) | 0.5341 (4) | 0.2892 (2) | 0.0503 (13) | |
H5D1 | 0.5012 | 0.4912 | 0.2976 | 0.075* | |
H5D2 | 0.4707 | 0.5363 | 0.2486 | 0.075* | |
H5D3 | 0.3664 | 0.5130 | 0.2953 | 0.075* | |
C6D | 0.2675 (5) | 0.8278 (3) | 0.45104 (19) | 0.0432 (11) | |
H6D1 | 0.3034 | 0.7972 | 0.4751 | 0.052* | |
H6D2 | 0.2131 | 0.8593 | 0.4754 | 0.052* | |
C7D | 0.0796 (5) | 0.7668 (4) | 0.3668 (2) | 0.0446 (11) | |
H7D | 0.0528 | 0.8193 | 0.3744 | 0.053* | |
C8D | 0.0278 (5) | 0.6878 (4) | 0.3221 (2) | 0.0478 (12) | |
H8D | −0.0418 | 0.6745 | 0.2929 | 0.057* | |
C9D | 0.1938 (5) | 0.6706 (3) | 0.37649 (19) | 0.0363 (10) | |
C10D | 0.0738 (5) | 0.5352 (4) | 0.2884 (2) | 0.0492 (13) | |
H10D | 0.1485 | 0.5148 | 0.2939 | 0.074* | |
H10E | 0.0638 | 0.5372 | 0.2478 | 0.074* | |
H10F | −0.0079 | 0.4918 | 0.2973 | 0.074* | |
O1 | 0.6786 (3) | 1.1124 (2) | 0.37871 (12) | 0.0340 (7) | |
O2 | 0.8558 (3) | 1.1616 (2) | 0.28704 (13) | 0.0363 (7) | |
O3 | 0.7223 (3) | 1.1987 (2) | 0.19369 (12) | 0.0344 (7) | |
O4 | 0.4766 (3) | 1.1983 (2) | 0.19345 (12) | 0.0335 (6) | |
O5 | 0.3066 (3) | 1.1615 (2) | 0.28660 (12) | 0.0369 (7) | |
O6 | 0.4340 (3) | 1.1127 (2) | 0.37851 (12) | 0.0339 (7) | |
C1A | 0.5216 (4) | 1.1773 (3) | 0.13866 (19) | 0.0317 (9) | |
C2A | 0.6552 (4) | 1.1773 (3) | 0.13903 (18) | 0.0304 (9) | |
C3A | 0.8586 (4) | 1.2031 (4) | 0.1962 (2) | 0.0435 (11) | |
H3A1 | 0.9113 | 1.2468 | 0.1748 | 0.052* | |
H3A2 | 0.8636 | 1.1414 | 0.1779 | 0.052* | |
C4A | 0.9142 (4) | 1.2359 (4) | 0.2608 (2) | 0.0452 (12) | |
H4A1 | 1.0121 | 1.2532 | 0.2640 | 0.054* | |
H4A2 | 0.8920 | 1.2907 | 0.2812 | 0.054* | |
C5A | 0.8937 (4) | 1.1889 (3) | 0.34887 (19) | 0.0396 (10) | |
H5A1 | 0.8754 | 1.2461 | 0.3674 | 0.047* | |
H5A2 | 0.9901 | 1.2018 | 0.3561 | 0.047* | |
C6A | 0.8145 (4) | 1.1110 (3) | 0.37545 (19) | 0.0375 (10) | |
H6A1 | 0.8134 | 1.0506 | 0.3507 | 0.045* | |
H6A2 | 0.8559 | 1.1208 | 0.4150 | 0.045* | |
C7A | 0.5869 (5) | 1.0409 (3) | 0.39693 (16) | 0.0320 (9) | |
C8A | 0.4550 (4) | 1.0409 (3) | 0.39693 (16) | 0.0313 (9) | |
C9A | 0.2965 (5) | 1.1112 (3) | 0.37474 (19) | 0.0382 (10) | |
H9A1 | 0.2646 | 1.1207 | 0.4141 | 0.046* | |
H9A2 | 0.2373 | 1.0508 | 0.3497 | 0.046* | |
C10A | 0.2957 (5) | 1.1893 (3) | 0.3483 (2) | 0.0404 (11) | |
H10G | 0.2121 | 1.2022 | 0.3551 | 0.049* | |
H10H | 0.3711 | 1.2463 | 0.3670 | 0.049* | |
C11A | 0.3212 (5) | 1.2358 (4) | 0.2599 (2) | 0.0455 (12) | |
H11A | 0.3980 | 1.2909 | 0.2801 | 0.055* | |
H11B | 0.2403 | 1.2527 | 0.2628 | 0.055* | |
C12A | 0.3435 (5) | 1.2024 (4) | 0.1950 (2) | 0.0438 (11) | |
H12A | 0.2769 | 1.1405 | 0.1767 | 0.053* | |
H12B | 0.3345 | 1.2459 | 0.1734 | 0.053* | |
C13A | 0.7080 (4) | 1.1548 (3) | 0.08491 (18) | 0.0311 (9) | |
H13A | 0.7948 | 1.1515 | 0.0850 | 0.037* | |
C14A | 0.6355 (4) | 1.1370 (3) | 0.03055 (18) | 0.0299 (9) | |
C15A | 0.5010 (4) | 1.1365 (3) | 0.03027 (18) | 0.0296 (9) | |
C16A | 0.4464 (4) | 1.1551 (3) | 0.08463 (18) | 0.0306 (9) | |
H16A | 0.3567 | 1.1525 | 0.0846 | 0.037* | |
C17A | 0.6171 (5) | 0.9720 (3) | 0.41512 (17) | 0.0372 (10) | |
H17A | 0.7059 | 0.9725 | 0.4156 | 0.045* | |
C18A | 0.5160 (5) | 0.9009 (3) | 0.43301 (17) | 0.0376 (10) | |
C19A | 0.3853 (5) | 0.9012 (3) | 0.43272 (17) | 0.0379 (10) | |
C20A | 0.3553 (5) | 0.9719 (3) | 0.41488 (16) | 0.0346 (10) | |
H20A | 0.2671 | 0.9725 | 0.4151 | 0.042* | |
P1A | 0.19646 (11) | 0.39244 (7) | 0.14549 (5) | 0.0278 (2) | |
F1A | 0.1875 (3) | 0.37509 (17) | 0.21079 (11) | 0.0372 (6) | |
F2A | 0.0449 (2) | 0.39352 (18) | 0.14514 (11) | 0.0392 (6) | |
F3A | 0.2524 (3) | 0.50461 (16) | 0.17484 (10) | 0.0368 (6) | |
F4A | 0.2050 (3) | 0.40926 (17) | 0.08006 (10) | 0.0365 (6) | |
F5A | 0.3491 (2) | 0.39321 (18) | 0.14568 (11) | 0.0402 (6) | |
F6A | 0.1401 (3) | 0.28038 (16) | 0.11634 (11) | 0.0390 (6) | |
P1B | 0.0000 | 1.0000 | 0.5000 | 0.0398 (4) | |
F1B | −0.0190 (4) | 0.9672 (3) | 0.42946 (13) | 0.0703 (9) | |
F22B | 0.1506 (9) | 1.0019 (16) | 0.4994 (9) | 0.061 (5) | 0.30 |
F32B | −0.046 (2) | 0.8950 (7) | 0.5037 (11) | 0.062 (5) | 0.30 |
F23B | 0.1154 (13) | 0.9564 (11) | 0.4983 (8) | 0.080 (4) | 0.35 |
F33B | −0.1021 (11) | 0.9003 (6) | 0.5006 (6) | 0.059 (3) | 0.35 |
F21B | 0.1585 (8) | 1.0443 (11) | 0.5000 (10) | 0.079 (5) | 0.35 |
F31B | 0.0081 (15) | 0.9019 (7) | 0.5011 (9) | 0.067 (4) | 0.35 |
P1C | 1.0000 | 1.0000 | 0.0000 | 0.0819 (9) | |
F11C | 1.1315 (7) | 1.0416 (6) | 0.0452 (4) | 0.091 (2) | 0.70 |
F21C | 0.9550 (12) | 0.9040 (4) | 0.0199 (4) | 0.088 (2) | 0.70 |
F31C | 0.9107 (4) | 1.0365 (3) | 0.0469 (3) | 0.0743 (16) | 0.70 |
F12C | 1.1046 (19) | 1.0121 (15) | 0.0538 (9) | 0.100 (4) | 0.30 |
F22C | 0.934 (3) | 0.8909 (7) | −0.0044 (12) | 0.117 (7) | 0.30 |
F32C | 0.9967 (16) | 0.9995 (10) | 0.0678 (4) | 0.109 (4) | 0.30 |
C1AN | 0.9134 (9) | 0.8276 (9) | 0.1387 (4) | 0.055 (3) | 0.50 |
H1A1 | 0.9349 | 0.8854 | 0.1698 | 0.082* | 0.50 |
H1A2 | 0.8399 | 0.8219 | 0.1117 | 0.082* | 0.50 |
H1A3 | 0.9915 | 0.8279 | 0.1174 | 0.082* | 0.50 |
C2AN | 0.8752 (10) | 0.7509 (9) | 0.1639 (5) | 0.054 (3) | 0.50 |
N1AN | 0.8448 (10) | 0.6893 (9) | 0.1857 (5) | 0.077 (3) | 0.50 |
C1BN | 0.703 (2) | 0.4071 (14) | 0.1200 (8) | 0.146 (8)* | 0.75 |
H1B3 | 0.7262 | 0.4593 | 0.1552 | 0.218* | 0.75 |
H1B4 | 0.7608 | 0.3709 | 0.1210 | 0.218* | 0.75 |
H1B5 | 0.6102 | 0.3679 | 0.1187 | 0.218* | 0.75 |
C2BN | 0.7218 (18) | 0.4410 (10) | 0.0692 (6) | 0.112 (4)* | 0.75 |
N1BN | 0.7401 (10) | 0.4796 (7) | 0.0313 (5) | 0.105 (3)* | 0.75 |
C1CN | 0.697 (3) | 0.3958 (11) | 0.0953 (6) | 0.044 (5) | 0.25 |
H1C1 | 0.7124 | 0.4431 | 0.0741 | 0.065* | 0.25 |
H1C2 | 0.6053 | 0.3528 | 0.0855 | 0.065* | 0.25 |
H1C3 | 0.7583 | 0.3619 | 0.0841 | 0.065* | 0.25 |
C2CN | 0.720 (2) | 0.4395 (14) | 0.1575 (6) | 0.039 (4) | 0.25 |
N1CN | 0.7334 (18) | 0.4674 (16) | 0.2089 (6) | 0.064 (5) | 0.25 |
O2W | 0.8088 (13) | 0.6125 (9) | 0.4157 (6) | 0.043 (3)* | 0.25 |
H2WA | 0.762 (12) | 0.647 (9) | 0.432 (7) | 0.041 (9)* | 0.25 |
H2WB | 0.890 (6) | 0.646 (9) | 0.433 (7) | 0.041 (9)* | 0.25 |
O3W | 0.014 (2) | 0.0323 (16) | 0.2510 (11) | 0.093 (6)* | 0.25 |
H3WA | −0.040 (16) | 0.064 (13) | 0.252 (13) | 0.092 (10)* | 0.25 |
H3WB | 0.092 (9) | 0.077 (11) | 0.254 (13) | 0.092 (10)* | 0.25 |
O1W | 0.7268 (9) | 0.4509 (5) | 0.3262 (4) | 0.068 (2) | 0.50 |
H1WA | 0.677 (7) | 0.3972 (13) | 0.332 (4) | 0.063 (6)* | 0.50 |
H1WB | 0.739 (11) | 0.433 (5) | 0.2886 (15) | 0.061 (6)* | 0.50 |
O1M | 0.6277 (4) | 0.2579 (2) | 0.31771 (14) | 0.0453 (8) | |
H1MA | 0.607 (4) | 0.211 (2) | 0.333 (2) | 0.044 (5)* | |
H1MB | 0.702 (3) | 0.257 (3) | 0.302 (2) | 0.049 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Rh1 | 0.02500 (18) | 0.02144 (18) | 0.01569 (17) | 0.00805 (12) | −0.00344 (12) | 0.00066 (12) |
C1C | 0.058 (3) | 0.041 (3) | 0.031 (2) | 0.032 (2) | 0.003 (2) | −0.0012 (19) |
C2C | 0.043 (2) | 0.046 (3) | 0.0172 (18) | 0.021 (2) | 0.0062 (18) | 0.0013 (18) |
C3C | 0.068 (4) | 0.143 (7) | 0.043 (3) | 0.055 (4) | 0.021 (3) | 0.054 (4) |
C4C | 0.060 (3) | 0.148 (7) | 0.040 (3) | 0.047 (4) | 0.008 (3) | 0.056 (4) |
C5C | 0.032 (2) | 0.047 (3) | 0.0179 (18) | 0.0153 (19) | −0.0089 (17) | 0.0022 (17) |
C6C | 0.038 (2) | 0.040 (3) | 0.032 (2) | 0.002 (2) | −0.0161 (19) | −0.0012 (19) |
C7C | 0.064 (4) | 0.035 (3) | 0.120 (6) | 0.009 (3) | −0.038 (4) | −0.032 (3) |
C8C | 0.072 (4) | 0.032 (3) | 0.128 (6) | 0.017 (3) | 0.013 (4) | −0.027 (3) |
N1B | 0.0321 (18) | 0.0330 (18) | 0.0203 (16) | 0.0150 (14) | −0.0028 (14) | 0.0042 (14) |
N2B | 0.0285 (17) | 0.0281 (18) | 0.0261 (17) | 0.0104 (14) | −0.0047 (14) | 0.0015 (14) |
N3B | 0.0254 (16) | 0.0331 (18) | 0.0235 (16) | 0.0084 (14) | −0.0041 (14) | 0.0050 (14) |
N4B | 0.0277 (17) | 0.0289 (18) | 0.0239 (16) | 0.0092 (14) | 0.0000 (14) | 0.0014 (14) |
C1B | 0.037 (2) | 0.031 (2) | 0.029 (2) | 0.0174 (18) | 0.0014 (18) | 0.0083 (17) |
C2B | 0.029 (2) | 0.049 (3) | 0.025 (2) | 0.0188 (19) | −0.0056 (17) | 0.0055 (19) |
C3B | 0.031 (2) | 0.038 (2) | 0.027 (2) | 0.0100 (18) | −0.0098 (18) | −0.0006 (18) |
C4B | 0.0228 (18) | 0.026 (2) | 0.0224 (18) | 0.0102 (15) | −0.0001 (15) | 0.0008 (15) |
C5B | 0.039 (2) | 0.028 (2) | 0.042 (2) | 0.0070 (18) | −0.004 (2) | 0.0079 (19) |
C6B | 0.030 (2) | 0.031 (2) | 0.027 (2) | 0.0073 (17) | −0.0004 (17) | 0.0065 (17) |
C7B | 0.034 (2) | 0.041 (2) | 0.028 (2) | 0.0178 (19) | 0.0007 (18) | 0.0023 (18) |
C8B | 0.027 (2) | 0.049 (3) | 0.0229 (19) | 0.0155 (19) | 0.0049 (17) | 0.0045 (18) |
C9B | 0.0226 (18) | 0.0231 (19) | 0.0220 (18) | 0.0068 (15) | −0.0050 (15) | 0.0018 (15) |
C10B | 0.044 (2) | 0.028 (2) | 0.043 (2) | 0.0135 (19) | 0.006 (2) | 0.0092 (19) |
Rh2 | 0.0490 (2) | 0.0290 (2) | 0.0288 (2) | 0.01073 (16) | −0.00532 (17) | −0.00377 (15) |
C1E | 0.070 (4) | 0.035 (3) | 0.053 (3) | 0.021 (2) | 0.001 (3) | 0.006 (2) |
C2E | 0.071 (3) | 0.041 (3) | 0.036 (2) | 0.024 (2) | −0.003 (2) | 0.008 (2) |
C3E | 0.110 (6) | 0.136 (7) | 0.042 (3) | 0.079 (6) | −0.002 (4) | 0.013 (4) |
C4E | 0.066 (4) | 0.136 (7) | 0.043 (3) | 0.016 (4) | −0.006 (3) | 0.015 (4) |
C5E | 0.061 (3) | 0.042 (3) | 0.030 (2) | 0.003 (2) | 0.006 (2) | 0.007 (2) |
C6E | 0.052 (3) | 0.037 (3) | 0.054 (3) | 0.005 (2) | −0.004 (2) | 0.006 (2) |
C7E | 0.061 (4) | 0.035 (3) | 0.178 (9) | 0.005 (3) | −0.011 (5) | 0.032 (4) |
C8E | 0.078 (5) | 0.034 (3) | 0.178 (9) | 0.021 (3) | 0.027 (5) | 0.028 (4) |
N1D | 0.049 (2) | 0.035 (2) | 0.0308 (19) | 0.0139 (17) | −0.0159 (18) | 0.0006 (16) |
N2D | 0.042 (2) | 0.042 (2) | 0.037 (2) | 0.0175 (18) | −0.0125 (18) | −0.0065 (17) |
N3D | 0.047 (2) | 0.034 (2) | 0.0329 (19) | 0.0126 (17) | 0.0077 (17) | 0.0019 (16) |
N4D | 0.037 (2) | 0.043 (2) | 0.035 (2) | 0.0141 (17) | −0.0022 (17) | −0.0045 (17) |
C1D | 0.074 (3) | 0.033 (2) | 0.023 (2) | 0.014 (2) | −0.014 (2) | 0.0012 (18) |
C2D | 0.036 (2) | 0.048 (3) | 0.052 (3) | 0.015 (2) | −0.011 (2) | 0.009 (2) |
C3D | 0.033 (2) | 0.051 (3) | 0.055 (3) | 0.018 (2) | −0.011 (2) | −0.002 (2) |
C4D | 0.042 (2) | 0.032 (2) | 0.027 (2) | 0.0130 (19) | −0.0102 (19) | −0.0015 (17) |
C5D | 0.048 (3) | 0.049 (3) | 0.041 (3) | 0.019 (2) | −0.011 (2) | −0.012 (2) |
C6D | 0.066 (3) | 0.032 (2) | 0.022 (2) | 0.012 (2) | 0.010 (2) | 0.0004 (18) |
C7D | 0.035 (2) | 0.044 (3) | 0.052 (3) | 0.016 (2) | 0.010 (2) | 0.007 (2) |
C8D | 0.034 (2) | 0.057 (3) | 0.049 (3) | 0.021 (2) | 0.003 (2) | 0.002 (2) |
C9D | 0.041 (2) | 0.033 (2) | 0.027 (2) | 0.0103 (19) | 0.0000 (19) | −0.0016 (18) |
C10D | 0.045 (3) | 0.049 (3) | 0.039 (3) | 0.017 (2) | −0.008 (2) | −0.013 (2) |
O1 | 0.0407 (16) | 0.0329 (16) | 0.0259 (14) | 0.0113 (13) | −0.0031 (13) | 0.0054 (12) |
O2 | 0.0378 (16) | 0.0405 (17) | 0.0263 (14) | 0.0085 (13) | −0.0040 (13) | 0.0089 (13) |
O3 | 0.0340 (15) | 0.0422 (17) | 0.0265 (14) | 0.0113 (13) | −0.0012 (13) | 0.0115 (13) |
O4 | 0.0386 (16) | 0.0404 (17) | 0.0267 (14) | 0.0180 (13) | 0.0045 (13) | 0.0121 (13) |
O5 | 0.0503 (18) | 0.0416 (17) | 0.0241 (14) | 0.0225 (15) | 0.0032 (13) | 0.0092 (13) |
O6 | 0.0415 (16) | 0.0339 (16) | 0.0258 (14) | 0.0140 (13) | −0.0002 (13) | 0.0059 (12) |
C1A | 0.038 (2) | 0.031 (2) | 0.030 (2) | 0.0132 (18) | 0.0010 (18) | 0.0136 (17) |
C2A | 0.034 (2) | 0.029 (2) | 0.029 (2) | 0.0093 (17) | 0.0016 (18) | 0.0133 (17) |
C3A | 0.030 (2) | 0.064 (3) | 0.039 (2) | 0.009 (2) | 0.002 (2) | 0.027 (2) |
C4A | 0.029 (2) | 0.054 (3) | 0.043 (3) | −0.001 (2) | −0.008 (2) | 0.020 (2) |
C5A | 0.034 (2) | 0.046 (3) | 0.031 (2) | 0.009 (2) | −0.0103 (19) | 0.004 (2) |
C6A | 0.044 (2) | 0.045 (3) | 0.025 (2) | 0.018 (2) | −0.0053 (19) | 0.0078 (19) |
C7A | 0.048 (2) | 0.029 (2) | 0.0130 (17) | 0.0098 (18) | −0.0031 (17) | −0.0010 (15) |
C8A | 0.047 (2) | 0.029 (2) | 0.0135 (17) | 0.0116 (18) | −0.0010 (17) | −0.0004 (15) |
C9A | 0.040 (2) | 0.048 (3) | 0.024 (2) | 0.014 (2) | 0.0056 (19) | 0.0068 (19) |
C10A | 0.048 (3) | 0.047 (3) | 0.030 (2) | 0.027 (2) | 0.004 (2) | 0.003 (2) |
C11A | 0.055 (3) | 0.056 (3) | 0.044 (3) | 0.038 (3) | 0.014 (2) | 0.021 (2) |
C12A | 0.049 (3) | 0.063 (3) | 0.040 (3) | 0.037 (2) | 0.010 (2) | 0.027 (2) |
C13A | 0.033 (2) | 0.032 (2) | 0.032 (2) | 0.0133 (17) | 0.0001 (18) | 0.0135 (18) |
C14A | 0.040 (2) | 0.026 (2) | 0.0260 (19) | 0.0115 (17) | 0.0032 (17) | 0.0108 (16) |
C15A | 0.033 (2) | 0.027 (2) | 0.028 (2) | 0.0076 (17) | −0.0023 (17) | 0.0097 (16) |
C16A | 0.029 (2) | 0.037 (2) | 0.029 (2) | 0.0114 (17) | 0.0044 (17) | 0.0159 (18) |
C17A | 0.057 (3) | 0.034 (2) | 0.0153 (18) | 0.017 (2) | −0.0090 (19) | −0.0036 (16) |
C18A | 0.060 (3) | 0.027 (2) | 0.0170 (18) | 0.009 (2) | −0.0047 (19) | −0.0022 (16) |
C19A | 0.058 (3) | 0.029 (2) | 0.0163 (18) | 0.008 (2) | −0.0001 (19) | −0.0023 (16) |
C20A | 0.047 (3) | 0.032 (2) | 0.0140 (17) | 0.0071 (19) | 0.0001 (18) | −0.0025 (16) |
P1A | 0.0322 (5) | 0.0249 (5) | 0.0232 (5) | 0.0090 (4) | −0.0024 (4) | 0.0027 (4) |
F1A | 0.0494 (15) | 0.0320 (13) | 0.0295 (12) | 0.0109 (11) | 0.0015 (11) | 0.0117 (10) |
F2A | 0.0361 (13) | 0.0452 (15) | 0.0392 (14) | 0.0191 (11) | 0.0050 (11) | 0.0094 (12) |
F3A | 0.0531 (15) | 0.0251 (12) | 0.0273 (12) | 0.0085 (11) | −0.0008 (11) | 0.0054 (10) |
F4A | 0.0453 (14) | 0.0388 (14) | 0.0228 (11) | 0.0135 (11) | −0.0026 (10) | 0.0057 (10) |
F5A | 0.0335 (13) | 0.0446 (15) | 0.0415 (14) | 0.0144 (11) | −0.0043 (11) | 0.0089 (12) |
F6A | 0.0446 (14) | 0.0252 (12) | 0.0385 (14) | 0.0086 (11) | −0.0046 (11) | −0.0018 (10) |
P1B | 0.0355 (9) | 0.0525 (11) | 0.0317 (8) | 0.0184 (8) | −0.0011 (7) | 0.0079 (7) |
F1B | 0.090 (2) | 0.082 (2) | 0.0338 (16) | 0.0303 (19) | −0.0012 (16) | 0.0050 (15) |
F22B | 0.034 (6) | 0.088 (11) | 0.061 (6) | 0.031 (6) | −0.001 (6) | 0.008 (11) |
F32B | 0.055 (10) | 0.070 (6) | 0.063 (7) | 0.021 (6) | −0.011 (10) | 0.024 (5) |
F23B | 0.065 (7) | 0.083 (7) | 0.078 (6) | 0.019 (6) | −0.009 (6) | 0.009 (7) |
F33B | 0.048 (6) | 0.073 (6) | 0.053 (5) | 0.022 (5) | −0.008 (6) | 0.009 (4) |
F21B | 0.068 (7) | 0.080 (9) | 0.081 (7) | 0.030 (6) | 0.004 (5) | 0.003 (8) |
F31B | 0.054 (7) | 0.076 (6) | 0.066 (6) | 0.023 (5) | −0.002 (7) | 0.010 (5) |
P1C | 0.0369 (10) | 0.0391 (11) | 0.153 (3) | 0.0145 (9) | −0.0049 (14) | −0.0050 (14) |
F11C | 0.034 (4) | 0.060 (5) | 0.158 (6) | 0.008 (3) | −0.005 (4) | 0.007 (4) |
F21C | 0.097 (5) | 0.043 (3) | 0.104 (6) | 0.011 (3) | −0.014 (5) | 0.006 (3) |
F31C | 0.0227 (18) | 0.057 (3) | 0.125 (4) | 0.0214 (18) | −0.002 (2) | −0.016 (3) |
F12C | 0.028 (5) | 0.066 (7) | 0.174 (7) | 0.012 (5) | −0.001 (6) | −0.018 (6) |
F22C | 0.099 (10) | 0.043 (8) | 0.164 (14) | 0.007 (7) | −0.029 (12) | −0.028 (9) |
F32C | 0.069 (5) | 0.068 (5) | 0.150 (6) | 0.001 (5) | −0.005 (6) | −0.007 (6) |
C1AN | 0.031 (5) | 0.109 (9) | 0.028 (5) | 0.040 (5) | 0.004 (4) | 0.005 (5) |
C2AN | 0.024 (4) | 0.076 (8) | 0.061 (7) | 0.030 (5) | −0.002 (4) | 0.000 (6) |
N1AN | 0.046 (5) | 0.100 (9) | 0.073 (7) | 0.038 (6) | −0.016 (5) | −0.014 (6) |
C1CN | 0.087 (13) | 0.010 (7) | 0.015 (8) | −0.008 (7) | −0.010 (8) | 0.005 (6) |
C2CN | 0.041 (8) | 0.053 (9) | 0.020 (8) | 0.022 (7) | −0.012 (7) | 0.000 (7) |
N1CN | 0.044 (9) | 0.104 (13) | 0.036 (8) | 0.031 (9) | −0.009 (7) | −0.002 (9) |
O1W | 0.089 (5) | 0.045 (4) | 0.062 (4) | 0.012 (4) | 0.003 (4) | 0.015 (3) |
O1M | 0.055 (2) | 0.0443 (19) | 0.0305 (16) | 0.0154 (16) | 0.0011 (15) | 0.0024 (14) |
Rh1—C9B | 2.037 (4) | C10D—H10E | 0.9600 |
Rh1—C4B | 2.042 (4) | C10D—H10F | 0.9600 |
Rh1—C5C | 2.198 (4) | O1—C7A | 1.370 (5) |
Rh1—C6C | 2.203 (4) | O1—C6A | 1.438 (5) |
Rh1—C1C | 2.205 (4) | O2—C4A | 1.408 (6) |
Rh1—C2C | 2.208 (4) | O2—C5A | 1.408 (5) |
C1C—C2C | 1.371 (7) | O3—C2A | 1.359 (5) |
C1C—C8C | 1.495 (8) | O3—C3A | 1.412 (5) |
C1C—H1C | 0.9300 | O4—C1A | 1.362 (5) |
C2C—C3C | 1.497 (6) | O4—C12A | 1.422 (5) |
C2C—H2C | 0.9300 | O5—C10A | 1.407 (5) |
C3C—C4C | 1.417 (8) | O5—C11A | 1.417 (6) |
C3C—H3C | 0.9300 | O6—C8A | 1.379 (5) |
C4C—C5C | 1.503 (7) | O6—C9A | 1.440 (5) |
C4C—H4C | 0.9300 | C1A—C16A | 1.384 (6) |
C5C—C6C | 1.354 (7) | C1A—C2A | 1.404 (6) |
C5C—H5C | 0.9300 | C2A—C13A | 1.389 (6) |
C6C—C7C | 1.497 (8) | C3A—C4A | 1.506 (6) |
C6C—H6C | 0.9300 | C3A—H3A1 | 0.9700 |
C7C—C8C | 1.402 (9) | C3A—H3A2 | 0.9700 |
C7C—H7C | 0.9300 | C4A—H4A1 | 0.9700 |
C8C—H8C | 0.9300 | C4A—H4A2 | 0.9700 |
N1B—C4B | 1.350 (5) | C5A—C6A | 1.505 (6) |
N1B—C2B | 1.384 (5) | C5A—H5A1 | 0.9700 |
N1B—C1B | 1.468 (5) | C5A—H5A2 | 0.9700 |
N2B—C4B | 1.351 (5) | C6A—H6A1 | 0.9700 |
N2B—C3B | 1.389 (5) | C6A—H6A2 | 0.9700 |
N2B—C5B | 1.448 (5) | C7A—C17A | 1.378 (6) |
N3B—C9B | 1.351 (5) | C7A—C8A | 1.386 (6) |
N3B—C8B | 1.383 (5) | C8A—C20A | 1.382 (6) |
N3B—C6B | 1.475 (5) | C9A—C10A | 1.503 (7) |
N4B—C9B | 1.354 (5) | C9A—H9A1 | 0.9700 |
N4B—C7B | 1.385 (6) | C9A—H9A2 | 0.9700 |
N4B—C10B | 1.454 (6) | C10A—H10G | 0.9700 |
C1B—C14A | 1.515 (6) | C10A—H10H | 0.9700 |
C1B—H1B1 | 0.9700 | C11A—C12A | 1.514 (7) |
C1B—H1B2 | 0.9700 | C11A—H11A | 0.9700 |
C2B—C3B | 1.341 (7) | C11A—H11B | 0.9700 |
C2B—H2B | 0.9300 | C12A—H12A | 0.9700 |
C3B—H3B | 0.9300 | C12A—H12B | 0.9700 |
C5B—H5B1 | 0.9600 | C13A—C14A | 1.390 (6) |
C5B—H5B2 | 0.9600 | C13A—H13A | 0.9300 |
C5B—H5B3 | 0.9600 | C14A—C15A | 1.410 (6) |
C6B—C15A | 1.509 (5) | C15A—C16A | 1.395 (6) |
C6B—H6B1 | 0.9700 | C16A—H16A | 0.9300 |
C6B—H6B2 | 0.9700 | C17A—C18A | 1.409 (7) |
C7B—C8B | 1.345 (7) | C17A—H17A | 0.9300 |
C7B—H7B | 0.9300 | C18A—C19A | 1.375 (7) |
C8B—H8B | 0.9300 | C19A—C20A | 1.399 (6) |
C10B—H10A | 0.9600 | C20A—H20A | 0.9300 |
C10B—H10B | 0.9600 | P1A—F2A | 1.599 (3) |
C10B—H10C | 0.9600 | P1A—F5A | 1.600 (3) |
Rh2—C4D | 2.033 (5) | P1A—F6A | 1.606 (3) |
Rh2—C9D | 2.037 (5) | P1A—F3A | 1.608 (3) |
Rh2—C1E | 2.196 (5) | P1A—F4A | 1.608 (2) |
Rh2—C6E | 2.196 (5) | P1A—F1A | 1.608 (2) |
Rh2—C2E | 2.204 (5) | P1B—F31Bi | 1.570 (7) |
Rh2—C5E | 2.214 (5) | P1B—F31B | 1.570 (7) |
C1E—C2E | 1.383 (7) | P1B—F33Bi | 1.572 (7) |
C1E—C8E | 1.508 (8) | P1B—F33B | 1.572 (7) |
C1E—H1E | 0.9300 | P1B—F22Bi | 1.573 (7) |
C2E—C3E | 1.501 (9) | P1B—F22B | 1.573 (7) |
C2E—H2E | 0.9300 | P1B—F23B | 1.573 (7) |
C3E—C4E | 1.407 (10) | P1B—F23Bi | 1.573 (7) |
C3E—H3E1 | 0.9700 | P1B—F32B | 1.574 (7) |
C3E—H3E2 | 0.9700 | P1B—F32Bi | 1.574 (7) |
C4E—C5E | 1.507 (8) | P1B—F21Bi | 1.576 (7) |
C4E—H4E1 | 0.9700 | P1B—F21B | 1.576 (7) |
C4E—H4E2 | 0.9700 | P1C—F31C | 1.565 (4) |
C5E—C6E | 1.396 (7) | P1C—F31Cii | 1.565 (4) |
C5E—H5E | 0.9300 | P1C—F11Cii | 1.576 (5) |
C6E—C7E | 1.502 (8) | P1C—F11C | 1.576 (5) |
C6E—H6E | 0.9300 | P1C—F32Cii | 1.581 (8) |
C7E—C8E | 1.420 (10) | P1C—F32C | 1.581 (8) |
C7E—H7E | 0.9300 | P1C—F22C | 1.587 (8) |
C8E—H8E | 0.9300 | P1C—F22Cii | 1.587 (8) |
N1D—C4D | 1.351 (6) | P1C—F12C | 1.595 (8) |
N1D—C2D | 1.407 (7) | P1C—F12Cii | 1.595 (8) |
N1D—C1D | 1.456 (6) | P1C—F21C | 1.603 (5) |
N2D—C4D | 1.358 (6) | P1C—F21Cii | 1.603 (5) |
N2D—C3D | 1.403 (7) | F12C—F32C | 1.15 (3) |
N2D—C5D | 1.474 (6) | C1AN—C2AN | 1.407 (13) |
N3D—C9D | 1.359 (6) | C1AN—H1A1 | 0.9600 |
N3D—C7D | 1.385 (6) | C1AN—H1A2 | 0.9600 |
N3D—C6D | 1.468 (6) | C1AN—H1A3 | 0.9600 |
N4D—C9D | 1.355 (6) | C2AN—N1AN | 1.152 (12) |
N4D—C8D | 1.399 (6) | C1BN—C2BN | 1.404 (14) |
N4D—C10D | 1.466 (6) | C1BN—H1B3 | 0.9600 |
C1D—C18A | 1.516 (6) | C1BN—H1B4 | 0.9600 |
C1D—H1D1 | 0.9700 | C1BN—H1B5 | 0.9600 |
C1D—H1D2 | 0.9700 | C2BN—N1BN | 1.171 (12) |
C2D—C3D | 1.329 (7) | C1CN—C2CN | 1.417 (14) |
C2D—H2D | 0.9300 | C1CN—H1C1 | 0.9600 |
C3D—H3D | 0.9300 | C1CN—H1C2 | 0.9600 |
C5D—H5D1 | 0.9600 | C1CN—H1C3 | 0.9600 |
C5D—H5D2 | 0.9600 | C2CN—N1CN | 1.156 (13) |
C5D—H5D3 | 0.9600 | O2W—H2WA | 0.867 (10) |
C6D—C19A | 1.528 (7) | O2W—H2WB | 0.867 (11) |
C6D—H6D1 | 0.9700 | O3W—H3WA | 0.871 (11) |
C6D—H6D2 | 0.9700 | O3W—H3WB | 0.870 (11) |
C7D—C8D | 1.341 (7) | O1W—H1WA | 0.870 (10) |
C7D—H7D | 0.9300 | O1W—H1WB | 0.871 (10) |
C8D—H8D | 0.9300 | O1M—H1MA | 0.863 (10) |
C10D—H10D | 0.9600 | O1M—H1MB | 0.860 (10) |
C9B—Rh1—C4B | 92.09 (15) | O3—C3A—C4A | 108.0 (4) |
C9B—Rh1—C5C | 90.57 (15) | O3—C3A—H3A1 | 110.1 |
C4B—Rh1—C5C | 162.87 (17) | C4A—C3A—H3A1 | 110.1 |
C9B—Rh1—C6C | 90.60 (17) | O3—C3A—H3A2 | 110.1 |
C4B—Rh1—C6C | 160.89 (17) | C4A—C3A—H3A2 | 110.1 |
C5C—Rh1—C6C | 35.85 (17) | H3A1—C3A—H3A2 | 108.4 |
C9B—Rh1—C1C | 160.62 (18) | O2—C4A—C3A | 108.2 (4) |
C4B—Rh1—C1C | 90.47 (17) | O2—C4A—H4A1 | 110.1 |
C5C—Rh1—C1C | 92.62 (17) | C3A—C4A—H4A1 | 110.1 |
C6C—Rh1—C1C | 80.97 (19) | O2—C4A—H4A2 | 110.1 |
C9B—Rh1—C2C | 162.78 (16) | C3A—C4A—H4A2 | 110.1 |
C4B—Rh1—C2C | 90.74 (16) | H4A1—C4A—H4A2 | 108.4 |
C5C—Rh1—C2C | 81.94 (16) | O2—C5A—C6A | 109.3 (4) |
C6C—Rh1—C2C | 92.27 (18) | O2—C5A—H5A1 | 109.8 |
C1C—Rh1—C2C | 36.21 (18) | C6A—C5A—H5A1 | 109.8 |
C2C—C1C—C8C | 125.2 (5) | O2—C5A—H5A2 | 109.8 |
C2C—C1C—Rh1 | 72.0 (2) | C6A—C5A—H5A2 | 109.8 |
C8C—C1C—Rh1 | 108.7 (4) | H5A1—C5A—H5A2 | 108.3 |
C2C—C1C—H1C | 117.4 | O1—C6A—C5A | 107.6 (3) |
C8C—C1C—H1C | 117.4 | O1—C6A—H6A1 | 110.2 |
Rh1—C1C—H1C | 89.2 | C5A—C6A—H6A1 | 110.2 |
C1C—C2C—C3C | 124.7 (5) | O1—C6A—H6A2 | 110.2 |
C1C—C2C—Rh1 | 71.8 (3) | C5A—C6A—H6A2 | 110.2 |
C3C—C2C—Rh1 | 107.7 (3) | H6A1—C6A—H6A2 | 108.5 |
C1C—C2C—H2C | 117.6 | O1—C7A—C17A | 125.0 (4) |
C3C—C2C—H2C | 117.6 | O1—C7A—C8A | 115.6 (4) |
Rh1—C2C—H2C | 90.5 | C17A—C7A—C8A | 119.4 (4) |
C4C—C3C—C2C | 119.6 (5) | O6—C8A—C20A | 124.6 (4) |
C4C—C3C—H3C | 120.2 | O6—C8A—C7A | 115.6 (4) |
C2C—C3C—H3C | 120.2 | C20A—C8A—C7A | 119.9 (4) |
C3C—C4C—C5C | 119.2 (4) | O6—C9A—C10A | 107.5 (4) |
C3C—C4C—H4C | 120.4 | O6—C9A—H9A1 | 110.2 |
C5C—C4C—H4C | 120.4 | C10A—C9A—H9A1 | 110.2 |
C6C—C5C—C4C | 124.3 (5) | O6—C9A—H9A2 | 110.2 |
C6C—C5C—Rh1 | 72.3 (2) | C10A—C9A—H9A2 | 110.2 |
C4C—C5C—Rh1 | 108.0 (3) | H9A1—C9A—H9A2 | 108.5 |
C6C—C5C—H5C | 117.9 | O5—C10A—C9A | 108.8 (4) |
C4C—C5C—H5C | 117.9 | O5—C10A—H10G | 109.9 |
Rh1—C5C—H5C | 89.7 | C9A—C10A—H10G | 109.9 |
C5C—C6C—C7C | 126.1 (6) | O5—C10A—H10H | 109.9 |
C5C—C6C—Rh1 | 71.9 (2) | C9A—C10A—H10H | 109.9 |
C7C—C6C—Rh1 | 108.4 (3) | H10G—C10A—H10H | 108.3 |
C5C—C6C—H6C | 116.9 | O5—C11A—C12A | 108.2 (4) |
C7C—C6C—H6C | 116.9 | O5—C11A—H11A | 110.1 |
Rh1—C6C—H6C | 89.7 | C12A—C11A—H11A | 110.1 |
C8C—C7C—C6C | 119.5 (5) | O5—C11A—H11B | 110.1 |
C8C—C7C—H7C | 120.3 | C12A—C11A—H11B | 110.1 |
C6C—C7C—H7C | 120.3 | H11A—C11A—H11B | 108.4 |
C7C—C8C—C1C | 118.9 (5) | O4—C12A—C11A | 107.4 (4) |
C7C—C8C—H8C | 120.5 | O4—C12A—H12A | 110.2 |
C1C—C8C—H8C | 120.5 | C11A—C12A—H12A | 110.2 |
C4B—N1B—C2B | 110.7 (3) | O4—C12A—H12B | 110.2 |
C4B—N1B—C1B | 124.5 (3) | C11A—C12A—H12B | 110.2 |
C2B—N1B—C1B | 124.8 (3) | H12A—C12A—H12B | 108.5 |
C4B—N2B—C3B | 110.7 (3) | C2A—C13A—C14A | 122.2 (4) |
C4B—N2B—C5B | 125.4 (3) | C2A—C13A—H13A | 118.9 |
C3B—N2B—C5B | 123.9 (4) | C14A—C13A—H13A | 118.9 |
C9B—N3B—C8B | 111.2 (3) | C13A—C14A—C15A | 118.8 (4) |
C9B—N3B—C6B | 124.6 (3) | C13A—C14A—C1B | 117.9 (4) |
C8B—N3B—C6B | 124.2 (3) | C15A—C14A—C1B | 123.3 (3) |
C9B—N4B—C7B | 111.1 (3) | C16A—C15A—C14A | 118.7 (4) |
C9B—N4B—C10B | 124.7 (3) | C16A—C15A—C6B | 117.8 (4) |
C7B—N4B—C10B | 124.2 (4) | C14A—C15A—C6B | 123.4 (4) |
N1B—C1B—C14A | 111.6 (3) | C1A—C16A—C15A | 122.0 (4) |
N1B—C1B—H1B1 | 109.3 | C1A—C16A—H16A | 119.0 |
C14A—C1B—H1B1 | 109.3 | C15A—C16A—H16A | 119.0 |
N1B—C1B—H1B2 | 109.3 | C7A—C17A—C18A | 121.1 (5) |
C14A—C1B—H1B2 | 109.3 | C7A—C17A—H17A | 119.4 |
H1B1—C1B—H1B2 | 108.0 | C18A—C17A—H17A | 119.4 |
C3B—C2B—N1B | 107.1 (3) | C19A—C18A—C17A | 119.1 (4) |
C3B—C2B—H2B | 126.5 | C19A—C18A—C1D | 124.3 (4) |
N1B—C2B—H2B | 126.5 | C17A—C18A—C1D | 116.6 (4) |
C2B—C3B—N2B | 106.5 (4) | C18A—C19A—C20A | 119.6 (4) |
C2B—C3B—H3B | 126.7 | C18A—C19A—C6D | 123.7 (4) |
N2B—C3B—H3B | 126.7 | C20A—C19A—C6D | 116.7 (4) |
N1B—C4B—N2B | 105.0 (3) | C8A—C20A—C19A | 120.9 (4) |
N1B—C4B—Rh1 | 127.1 (3) | C8A—C20A—H20A | 119.6 |
N2B—C4B—Rh1 | 127.7 (3) | C19A—C20A—H20A | 119.6 |
N2B—C5B—H5B1 | 109.5 | F2A—P1A—F5A | 178.98 (15) |
N2B—C5B—H5B2 | 109.5 | F2A—P1A—F6A | 90.39 (14) |
H5B1—C5B—H5B2 | 109.5 | F5A—P1A—F6A | 90.49 (14) |
N2B—C5B—H5B3 | 109.5 | F2A—P1A—F3A | 89.45 (15) |
H5B1—C5B—H5B3 | 109.5 | F5A—P1A—F3A | 89.67 (15) |
H5B2—C5B—H5B3 | 109.5 | F6A—P1A—F3A | 179.78 (18) |
N3B—C6B—C15A | 111.6 (3) | F2A—P1A—F4A | 89.73 (14) |
N3B—C6B—H6B1 | 109.3 | F5A—P1A—F4A | 89.75 (14) |
C15A—C6B—H6B1 | 109.3 | F6A—P1A—F4A | 90.21 (14) |
N3B—C6B—H6B2 | 109.3 | F3A—P1A—F4A | 89.94 (13) |
C15A—C6B—H6B2 | 109.3 | F2A—P1A—F1A | 90.22 (14) |
H6B1—C6B—H6B2 | 108.0 | F5A—P1A—F1A | 90.31 (14) |
C8B—C7B—N4B | 106.6 (4) | F6A—P1A—F1A | 89.52 (14) |
C8B—C7B—H7B | 126.7 | F3A—P1A—F1A | 90.33 (13) |
N4B—C7B—H7B | 126.7 | F4A—P1A—F1A | 179.73 (17) |
C7B—C8B—N3B | 106.7 (4) | F31Bi—P1B—F31B | 179.997 (8) |
C7B—C8B—H8B | 126.7 | F31B—P1B—F33Bi | 137.1 (6) |
N3B—C8B—H8B | 126.7 | F31Bi—P1B—F33B | 137.1 (6) |
N3B—C9B—N4B | 104.4 (3) | F33Bi—P1B—F33B | 179.999 (3) |
N3B—C9B—Rh1 | 127.1 (3) | F31Bi—P1B—F22Bi | 68.8 (9) |
N4B—C9B—Rh1 | 128.3 (3) | F31B—P1B—F22Bi | 111.2 (9) |
N4B—C10B—H10A | 109.5 | F33Bi—P1B—F22Bi | 111.7 (8) |
N4B—C10B—H10B | 109.5 | F33B—P1B—F22Bi | 68.3 (8) |
H10A—C10B—H10B | 109.5 | F31Bi—P1B—F22B | 111.2 (9) |
N4B—C10B—H10C | 109.5 | F31B—P1B—F22B | 68.8 (9) |
H10A—C10B—H10C | 109.5 | F33Bi—P1B—F22B | 68.3 (8) |
H10B—C10B—H10C | 109.5 | F33B—P1B—F22B | 111.7 (8) |
C4D—Rh2—C9D | 93.91 (18) | F22Bi—P1B—F22B | 180.0 (17) |
C4D—Rh2—C1E | 90.3 (2) | F31Bi—P1B—F23B | 136.0 (7) |
C9D—Rh2—C1E | 163.54 (19) | F33Bi—P1B—F23B | 93.1 (7) |
C4D—Rh2—C6E | 163.53 (19) | F33B—P1B—F23B | 86.9 (7) |
C9D—Rh2—C6E | 90.5 (2) | F22Bi—P1B—F23B | 155.2 (7) |
C1E—Rh2—C6E | 81.3 (2) | F31B—P1B—F23Bi | 136.0 (7) |
C4D—Rh2—C2E | 89.0 (2) | F33Bi—P1B—F23Bi | 86.9 (7) |
C9D—Rh2—C2E | 159.12 (18) | F33B—P1B—F23Bi | 93.1 (7) |
C1E—Rh2—C2E | 36.66 (19) | F22B—P1B—F23Bi | 155.2 (7) |
C6E—Rh2—C2E | 92.5 (2) | F23B—P1B—F23Bi | 179.996 (9) |
C4D—Rh2—C5E | 158.85 (18) | F31Bi—P1B—F32B | 159.8 (8) |
C9D—Rh2—C5E | 88.8 (2) | F33Bi—P1B—F32B | 157.0 (6) |
C1E—Rh2—C5E | 93.1 (2) | F22Bi—P1B—F32B | 91.1 (10) |
C6E—Rh2—C5E | 36.91 (19) | F22B—P1B—F32B | 88.9 (10) |
C2E—Rh2—C5E | 81.4 (2) | F23B—P1B—F32B | 64.2 (8) |
C2E—C1E—C8E | 125.6 (6) | F23Bi—P1B—F32B | 115.8 (9) |
C2E—C1E—Rh2 | 72.0 (3) | F31B—P1B—F32Bi | 159.8 (8) |
C8E—C1E—Rh2 | 108.9 (4) | F33B—P1B—F32Bi | 157.0 (6) |
C2E—C1E—H1E | 117.2 | F22Bi—P1B—F32Bi | 88.9 (10) |
C8E—C1E—H1E | 117.2 | F22B—P1B—F32Bi | 91.1 (10) |
Rh2—C1E—H1E | 89.1 | F23B—P1B—F32Bi | 115.8 (9) |
C1E—C2E—C3E | 125.7 (6) | F23Bi—P1B—F32Bi | 64.2 (8) |
C1E—C2E—Rh2 | 71.4 (3) | F32B—P1B—F32Bi | 179.999 (8) |
C3E—C2E—Rh2 | 108.7 (4) | F31Bi—P1B—F21Bi | 92.0 (8) |
C1E—C2E—H2E | 117.2 | F31B—P1B—F21Bi | 88.0 (8) |
C3E—C2E—H2E | 117.2 | F33Bi—P1B—F21Bi | 135.0 (7) |
Rh2—C2E—H2E | 89.9 | F33B—P1B—F21Bi | 45.0 (7) |
C4E—C3E—C2E | 118.9 (6) | F22B—P1B—F21Bi | 156.7 (8) |
C4E—C3E—H3E1 | 107.6 | F23B—P1B—F21Bi | 131.9 (8) |
C2E—C3E—H3E1 | 107.6 | F23Bi—P1B—F21Bi | 48.1 (8) |
C4E—C3E—H3E2 | 107.6 | F32B—P1B—F21Bi | 67.9 (9) |
C2E—C3E—H3E2 | 107.6 | F32Bi—P1B—F21Bi | 112.1 (9) |
H3E1—C3E—H3E2 | 107.0 | F31Bi—P1B—F21B | 88.0 (8) |
C3E—C4E—C5E | 119.9 (6) | F31B—P1B—F21B | 92.0 (8) |
C3E—C4E—H4E1 | 107.4 | F33Bi—P1B—F21B | 45.0 (7) |
C5E—C4E—H4E1 | 107.4 | F33B—P1B—F21B | 135.0 (7) |
C3E—C4E—H4E2 | 107.4 | F22Bi—P1B—F21B | 156.7 (8) |
C5E—C4E—H4E2 | 107.4 | F23B—P1B—F21B | 48.1 (8) |
H4E1—C4E—H4E2 | 106.9 | F23Bi—P1B—F21B | 131.9 (8) |
C6E—C5E—C4E | 124.4 (6) | F32B—P1B—F21B | 112.1 (9) |
C6E—C5E—Rh2 | 70.9 (3) | F32Bi—P1B—F21B | 67.9 (9) |
C4E—C5E—Rh2 | 107.8 (4) | F21Bi—P1B—F21B | 179.998 (2) |
C6E—C5E—H5E | 117.8 | F31C—P1C—F31Cii | 180.0 (3) |
C4E—C5E—H5E | 117.8 | F31C—P1C—F11Cii | 86.0 (5) |
Rh2—C5E—H5E | 91.4 | F31Cii—P1C—F11Cii | 94.0 (4) |
C5E—C6E—C7E | 125.6 (6) | F31C—P1C—F11C | 94.0 (4) |
C5E—C6E—Rh2 | 72.2 (3) | F31Cii—P1C—F11C | 86.0 (5) |
C7E—C6E—Rh2 | 109.2 (4) | F11Cii—P1C—F11C | 179.998 (2) |
C5E—C6E—H6E | 117.2 | F31C—P1C—F32Cii | 128.4 (6) |
C7E—C6E—H6E | 117.2 | F31Cii—P1C—F32Cii | 51.6 (6) |
Rh2—C6E—H6E | 88.5 | F11Cii—P1C—F32Cii | 57.1 (6) |
C8E—C7E—C6E | 118.7 (5) | F11C—P1C—F32Cii | 122.9 (6) |
C8E—C7E—H7E | 120.7 | F31C—P1C—F32C | 51.6 (6) |
C6E—C7E—H7E | 120.7 | F31Cii—P1C—F32C | 128.4 (6) |
C7E—C8E—C1E | 118.5 (5) | F11Cii—P1C—F32C | 122.9 (6) |
C7E—C8E—H8E | 120.8 | F11C—P1C—F32C | 57.1 (6) |
C1E—C8E—H8E | 120.8 | F32Cii—P1C—F32C | 179.999 (5) |
C4D—N1D—C2D | 110.8 (4) | F31C—P1C—F22C | 98.0 (14) |
C4D—N1D—C1D | 124.6 (4) | F31Cii—P1C—F22C | 82.0 (14) |
C2D—N1D—C1D | 124.6 (4) | F11Cii—P1C—F22C | 72.3 (10) |
C4D—N2D—C3D | 111.6 (4) | F11C—P1C—F22C | 107.7 (10) |
C4D—N2D—C5D | 124.9 (4) | F32Cii—P1C—F22C | 102.4 (11) |
C3D—N2D—C5D | 123.5 (4) | F32C—P1C—F22C | 77.6 (11) |
C9D—N3D—C7D | 111.3 (4) | F31C—P1C—F22Cii | 82.0 (14) |
C9D—N3D—C6D | 123.5 (4) | F31Cii—P1C—F22Cii | 98.0 (14) |
C7D—N3D—C6D | 125.2 (4) | F11Cii—P1C—F22Cii | 107.7 (10) |
C9D—N4D—C8D | 111.6 (4) | F11C—P1C—F22Cii | 72.3 (10) |
C9D—N4D—C10D | 124.9 (4) | F32Cii—P1C—F22Cii | 77.6 (11) |
C8D—N4D—C10D | 123.4 (4) | F32C—P1C—F22Cii | 102.4 (11) |
N1D—C1D—C18A | 113.3 (3) | F22C—P1C—F22Cii | 179.997 (9) |
N1D—C1D—H1D1 | 108.9 | F31C—P1C—F12C | 88.6 (10) |
C18A—C1D—H1D1 | 108.9 | F31Cii—P1C—F12C | 91.4 (10) |
N1D—C1D—H1D2 | 108.9 | F11Cii—P1C—F12C | 160.4 (8) |
C18A—C1D—H1D2 | 108.9 | F32Cii—P1C—F12C | 137.7 (10) |
H1D1—C1D—H1D2 | 107.7 | F22C—P1C—F12C | 89.8 (12) |
C3D—C2D—N1D | 107.4 (4) | F22Cii—P1C—F12C | 90.2 (12) |
C3D—C2D—H2D | 126.3 | F31C—P1C—F12Cii | 91.4 (10) |
N1D—C2D—H2D | 126.3 | F31Cii—P1C—F12Cii | 88.6 (10) |
C2D—C3D—N2D | 106.1 (5) | F11C—P1C—F12Cii | 160.4 (8) |
C2D—C3D—H3D | 127.0 | F32C—P1C—F12Cii | 137.7 (10) |
N2D—C3D—H3D | 127.0 | F22C—P1C—F12Cii | 90.2 (12) |
N1D—C4D—N2D | 104.2 (4) | F22Cii—P1C—F12Cii | 89.8 (12) |
N1D—C4D—Rh2 | 126.1 (3) | F12C—P1C—F12Cii | 179.998 (4) |
N2D—C4D—Rh2 | 129.0 (3) | F31C—P1C—F21C | 88.5 (5) |
N2D—C5D—H5D1 | 109.5 | F31Cii—P1C—F21C | 91.5 (5) |
N2D—C5D—H5D2 | 109.5 | F11Cii—P1C—F21C | 89.5 (4) |
H5D1—C5D—H5D2 | 109.5 | F11C—P1C—F21C | 90.5 (4) |
N2D—C5D—H5D3 | 109.5 | F32Cii—P1C—F21C | 122.0 (6) |
H5D1—C5D—H5D3 | 109.5 | F32C—P1C—F21C | 58.0 (6) |
H5D2—C5D—H5D3 | 109.5 | F22Cii—P1C—F21C | 159.6 (9) |
N3D—C6D—C19A | 112.6 (3) | F12C—P1C—F21C | 71.4 (8) |
N3D—C6D—H6D1 | 109.1 | F12Cii—P1C—F21C | 108.6 (8) |
C19A—C6D—H6D1 | 109.1 | F31C—P1C—F21Cii | 91.5 (5) |
N3D—C6D—H6D2 | 109.1 | F31Cii—P1C—F21Cii | 88.5 (5) |
C19A—C6D—H6D2 | 109.1 | F11Cii—P1C—F21Cii | 90.5 (4) |
H6D1—C6D—H6D2 | 107.8 | F11C—P1C—F21Cii | 89.5 (4) |
C8D—C7D—N3D | 107.3 (4) | F32Cii—P1C—F21Cii | 58.0 (6) |
C8D—C7D—H7D | 126.3 | F32C—P1C—F21Cii | 122.0 (6) |
N3D—C7D—H7D | 126.3 | F22C—P1C—F21Cii | 159.6 (9) |
C7D—C8D—N4D | 105.9 (4) | F12C—P1C—F21Cii | 108.6 (8) |
C7D—C8D—H8D | 127.0 | F12Cii—P1C—F21Cii | 71.4 (8) |
N4D—C8D—H8D | 127.0 | F21C—P1C—F21Cii | 179.998 (3) |
N4D—C9D—N3D | 103.8 (4) | F32C—F12C—P1C | 68.2 (7) |
N4D—C9D—Rh2 | 129.1 (3) | F12C—F32C—P1C | 69.5 (7) |
N3D—C9D—Rh2 | 126.3 (3) | C2AN—C1AN—H1A1 | 109.5 |
N4D—C10D—H10D | 109.5 | C2AN—C1AN—H1A2 | 109.5 |
N4D—C10D—H10E | 109.5 | H1A1—C1AN—H1A2 | 109.5 |
H10D—C10D—H10E | 109.5 | C2AN—C1AN—H1A3 | 109.5 |
N4D—C10D—H10F | 109.5 | H1A1—C1AN—H1A3 | 109.5 |
H10D—C10D—H10F | 109.5 | H1A2—C1AN—H1A3 | 109.5 |
H10E—C10D—H10F | 109.5 | N1AN—C2AN—C1AN | 178.6 (14) |
C7A—O1—C6A | 116.5 (3) | N1BN—C2BN—C1BN | 172.1 (17) |
C4A—O2—C5A | 111.9 (3) | C2CN—C1CN—H1C1 | 109.5 |
C2A—O3—C3A | 117.9 (3) | C2CN—C1CN—H1C2 | 109.5 |
C1A—O4—C12A | 116.9 (3) | H1C1—C1CN—H1C2 | 109.5 |
C10A—O5—C11A | 111.7 (4) | C2CN—C1CN—H1C3 | 109.5 |
C8A—O6—C9A | 116.7 (3) | H1C1—C1CN—H1C3 | 109.5 |
O4—C1A—C16A | 125.4 (4) | H1C2—C1CN—H1C3 | 109.5 |
O4—C1A—C2A | 115.2 (3) | N1CN—C2CN—C1CN | 174 (2) |
C16A—C1A—C2A | 119.3 (4) | H2WA—O2W—H2WB | 101.5 (16) |
O3—C2A—C13A | 125.2 (4) | H3WA—O3W—H3WB | 100.7 (16) |
O3—C2A—C1A | 116.0 (4) | H1WA—O1W—H1WB | 100.5 (16) |
C13A—C2A—C1A | 118.8 (4) | H1MA—O1M—H1MB | 102.6 (16) |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+2, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1M—H1MB···O2iii | 0.86 (1) | 2.51 (3) | 3.226 (5) | 141 (3) |
O1M—H1MB···O3iii | 0.86 (1) | 2.50 (4) | 3.076 (4) | 125 (4) |
O1M—H1MA···O1iii | 0.86 (1) | 2.38 (3) | 3.149 (5) | 149 (4) |
O1M—H1MA···O6iii | 0.86 (1) | 2.39 (2) | 3.138 (5) | 145 (4) |
O3W—H3WB···O5iii | 0.87 (1) | 2.21 (9) | 3.03 (2) | 158 (23) |
O3W—H3WA···O2iv | 0.87 (1) | 2.16 (10) | 2.99 (2) | 160 (27) |
O1W—H1WA···O1M | 0.87 (1) | 2.00 (1) | 2.796 (9) | 151 (3) |
O1W—H1WB···N1CN | 0.87 (1) | 2.06 (6) | 2.805 (18) | 143 (9) |
Symmetry codes: (iii) x, y−1, z; (iv) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Rh2(C8H12)2(C40H42N8O6)](PF6)2·1.5C2H3N·2H2O |
Mr | 1540.55 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 10.510 (2), 15.630 (3), 23.280 (5) |
α, β, γ (°) | 104.69 (3), 90.20 (3), 109.58 (3) |
V (Å3) | 3468.9 (12) |
Z | 2 |
Radiation type | Synchrotron, λ = 0.71073 Å |
µ (mm−1) | 0.61 |
Crystal size (mm) | 0.03 × 0.02 × 0.01 |
Data collection | |
Diffractometer | 3-BM1 Australian Synchrotron |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 43942, 11473, 9939 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.164, 1.33 |
No. of reflections | 11473 |
No. of parameters | 964 |
No. of restraints | 270 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.15, −1.40 |
Computer programs: BLU-ICE (McPhillips et al., 2002), XDS (Kabsch, 1993), SHELXS97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O1M—H1MB···O2i | 0.860 (10) | 2.51 (3) | 3.226 (5) | 141 (3) |
O1M—H1MB···O3i | 0.860 (10) | 2.50 (4) | 3.076 (4) | 125 (4) |
O1M—H1MA···O1i | 0.863 (10) | 2.38 (3) | 3.149 (5) | 149 (4) |
O1M—H1MA···O6i | 0.863 (10) | 2.39 (2) | 3.138 (5) | 145 (4) |
O3W—H3WB···O5i | 0.870 (11) | 2.21 (9) | 3.03 (2) | 158 (23) |
O3W—H3WA···O2ii | 0.871 (11) | 2.16 (10) | 2.99 (2) | 160 (27) |
O1W—H1WA···O1M | 0.870 (10) | 2.001 (10) | 2.796 (9) | 151 (3) |
O1W—H1WB···N1CN | 0.871 (10) | 2.06 (6) | 2.805 (18) | 143 (9) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y−1, z. |
Acknowledgements
The authors thank the Australian Research Council (DP0988410) for financial support. They also thank the Australian Synchrotron Facility, Melbourne, for the X-ray data.
References
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kabsch, W. (1993). J. Appl. Cryst. 26, 795–800. CrossRef CAS Web of Science IUCr Journals Google Scholar
Mata, J. A., Chianese, A. R., Miecznikowski, J. R., Poyatos, M., Peris, E., Faller, J. W. & Crabtree, R. H. (2004). Organometallics, 23, 1253–1263. Web of Science CSD CrossRef CAS Google Scholar
McPhillips, T. M., McPhillips, S. E., Chiu, H.-J., Cohen, A. E., Deacon, A. M., Ellis, P. J., Garman, E., Gonzalez, A., Sauter, N. K., Phizackerley, R. P., Soltis, S. M. & Kuhn, P. (2002). J. Synchrotron Rad. 9, 401–406. Web of Science CrossRef CAS IUCr Journals Google Scholar
Riederer, S. K. U., Gigler, P., Högerl, M. P., Herdtweck, E., Bechlars, B., Herrmann, W. A. & Kühn, F. (2010). Organometallics, 29, 5681–5692. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shrestha, S., Gimbert-Suriñach, C., Bhadbhade, M. & Colbran, S. B. (2011). Eur. J. Inorg. Chem. 28, 4331–4337. Web of Science CSD CrossRef Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals 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 sum of the acute C(NHC)-Rh-{C=C(centroid) for COD} bond angles is 360.2° for Rh1 and 359.3° for Rh2 indicative for the planarity of these centres. The Rh–C bond lengths are in the normal range (Mata et al., 2004; Riederer et al., 2010; Shrestha et al., 2011): 2.033 (4) - 2.042 (4) Å for the Rh—C(NHC) and 2.196 (5) - 2.214 (5) Å for the Rh–C(COD) distances. The dibenzo-18-crown-6 bridge adopts an 'umbrella' shape and forms hydrogen bonds with a centrally located water molecule (O1M; see Fig. 2). Other lattice water with partial occupancy are observed in the structure and are depicted in Fig. 2. To use the nomenclature introduced in Shrestha et al. (2011), the Rh(NHC)2(COD) centres are aligned 'up-and-out' for Rh1 and 'down-and-out' for Rh2.