# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 186/2295 data_7a _publ_author_name ; Elke Bleuel, P. Schwab, M. Laubender and Helmut Werner ; _publ_author_address ; Prof. Dr. Helmut Werner Institut f\"ur Anorganische Chemie Universit\"at W\"urzburg Am Hubland D-97074 W\"urzburg Deutschland ; _publ_contact_author ; Prof. Dr. Helmut Werner Institut f\"ur Anorganische Chemie Universit\"at W\"urzburg Am Hubland D-97074 W\"urzburg Deutschland ; _publ_contact_author_phone '049 931 888 5261' _publ_contact_author_fax '049 931 888 4605' _publ_contact_author_email helmut.werner@mail.uni-wuerzburg.de _publ_requested_journal 'Dalton - Transactions' _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication in "Dalton - Tansactions" ; _publ_section_title ; Carbenerhodium(I) complexes of the halfsandwich-type: Reactions with electrophiles ; _publ_section_abstract ; The reaction of the carbenerhodium(I) complexes [((5-C5H5)Rh(=CR2)(L)] (R = aryl) with HX (X = Cl, CF3CO2) led, depending on the size and donor properties of the ligand L, to two different type of products. While compounds 1, 2 with R = Ph and L = CO or PMe3 react with HX to give rhodium(III) alkyls [((5-C5H5)RhX(CHPh2)(L)] 3, 4a,b, the analogues 5a and 5b with R = Ph, p-Tol and L = PPri3 afford upon treatment with HX (X = Cl, Br, I, CF3CO2) the ring-substituted products [{h5-C5H4(CHR2)}RhHX(PPri3)] 6a-e. In the presence of excess HX, the latter are converted into the dihalo or bis(trifluoroacetato) derivatives [{h5-C5H4(CHR2)}RhX2(PPri3)] 7a-e. A labelling experiment using [((5-C5D5)Rh(=CPh2)(PPri3)] 5a-d5 as a precursor indicates that the migratory insertion of the carbene into a C-H bond of the cyclopentadienyl ring probably occurs via a (4-cyclopentadienerhodium(I) species as an intermediate. The triphenylphosphine complex [{h5-C5H4(CHPh2)}RhCl2(PPh3)] 7f was prepared analogously from 5c and two equivof HCl. The reactions of 5a and 5d (R = Ph, L = SbPri3) with either HBF4, [Me3O]BF4 or methyl triflate give via attack of the electrophile to the carbene carbon atom and subsequent (/( rearrangement cationic (3-benzylrhodium(III) complexes 9 and 10a-c in good to excellent yields. Treatment of 5a and 5d with iodine results in the cleavage of the metal-carbene bond and affords the diiodo compounds [((5-C5H5)RhI2(L)] 12a,b. ; _publ_section_exptl_prep ; Crystals were grown from acetone ao -20_C ; _publ_section_exptl_refinement ; ? ; _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H36 Cl2 P Rh' _chemical_formula_weight 565.34 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Rh' 'Rh' -1.2870 0.9190 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'C 1 c 1' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.865(2) _cell_length_b 23.214(2) _cell_length_c 13.172(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.85(1) _cell_angle_gamma 90.00 _cell_volume 2594(1) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description rhomb _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method ? _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.931 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; empirical absorption correction by psi-scans from 6 reflections with chi-angles near 90 degrees ; _exptl_special_details ; crystals grown from an acetone solution at -20_C ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CAD4 (Enraf-Nonius)' _diffrn_measurement_method 'Omega scans' _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_reflns_number 3624 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.92 _reflns_number_total 3624 _reflns_number_observed 3488 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 (Enraf-Nonius)' _computing_cell_refinement 'CAD4 (Enraf-Nonius)' _computing_data_reduction 'BEGIN (SDP)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+2.0436P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 3624 _refine_ls_number_parameters 290 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_obs 0.0284 _refine_ls_wR_factor_all 0.0698 _refine_ls_wR_factor_obs 0.0675 _refine_ls_goodness_of_fit_all 1.074 _refine_ls_goodness_of_fit_obs 1.061 _refine_ls_restrained_S_all 1.074 _refine_ls_restrained_S_obs 1.061 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Rh Rh 0.43833(3) 0.256302(10) 0.22116(3) 0.01742(7) Uani 1 d . . P P 0.58963(11) 0.33597(4) 0.20555(8) 0.0200(2) Uani 1 d . . Cl1 Cl 0.20472(12) 0.31005(5) 0.14278(9) 0.0325(2) Uani 1 d . . Cl2 Cl 0.44335(13) 0.21204(5) 0.05748(8) 0.0277(2) Uani 1 d . . C1 C 0.5665(5) 0.1866(2) 0.3159(3) 0.0252(8) Uani 1 d . . H1 H 0.6488(5) 0.1681(2) 0.2956(3) 0.030 Uiso 1 calc R . C2 C 0.5827(6) 0.2366(2) 0.3806(3) 0.0283(9) Uani 1 d . . H2 H 0.6786(6) 0.2553(2) 0.4166(3) 0.034 Uiso 1 calc R . C3 C 0.4292(6) 0.2535(2) 0.3813(3) 0.0280(9) Uani 1 d . . H3 H 0.4032(6) 0.2875(2) 0.4128(3) 0.034 Uiso 1 calc R . C4 C 0.3192(5) 0.2102(2) 0.3257(3) 0.0243(8) Uani 1 d . . H4 H 0.2091(5) 0.2098(2) 0.3174(3) 0.029 Uiso 1 calc R . C5 C 0.4020(5) 0.1687(2) 0.2863(3) 0.0240(8) Uani 1 d . . C6 C 0.3412(5) 0.1148(2) 0.2249(4) 0.0244(8) Uani 1 d . . H6 H 0.3460(56) 0.1185(21) 0.1609(38) 0.020(12) Uiso 1 d . . C10 C 0.6297(5) 0.3761(2) 0.3337(3) 0.0268(9) Uani 1 d . . H10 H 0.6459(5) 0.3458(2) 0.3898(3) 0.032 Uiso 1 calc R . C11 C 0.7856(5) 0.3215(2) 0.1888(3) 0.0277(9) Uani 1 d . . H11 H 0.8469(5) 0.3582(2) 0.2042(3) 0.033 Uiso 1 calc R . C12 C 0.4905(6) 0.3885(2) 0.1008(4) 0.0289(9) Uani 1 d . . H12 H 0.3989(6) 0.4040(2) 0.1222(4) 0.035 Uiso 1 calc R . C13 C 0.7781(6) 0.4135(2) 0.3663(4) 0.0377(11) Uani 1 d . . H13A H 0.7690(21) 0.4446(10) 0.3146(18) 0.056 Uiso 1 calc R . H13B H 0.8705(8) 0.3898(4) 0.3684(30) 0.056 Uiso 1 calc R . H13C H 0.7898(26) 0.4300(14) 0.4366(14) 0.056 Uiso 1 calc R . C14 C 0.4832(7) 0.4091(2) 0.3386(4) 0.0390(11) Uani 1 d . . H14A H 0.3907(10) 0.3841(6) 0.3150(31) 0.058 Uiso 1 calc R . H14B H 0.4690(28) 0.4429(10) 0.2921(25) 0.058 Uiso 1 calc R . H14C H 0.4959(21) 0.4216(15) 0.4116(7) 0.058 Uiso 1 calc R . C15 C 0.8758(6) 0.2768(3) 0.2675(4) 0.0424(12) Uani 1 d . . H15A H 0.8740(44) 0.2873(10) 0.3391(6) 0.064 Uiso 1 calc R . H15B H 0.9852(14) 0.2752(13) 0.2651(25) 0.064 Uiso 1 calc R . H15C H 0.8265(31) 0.2390(4) 0.2489(21) 0.064 Uiso 1 calc R . C16 C 0.7787(6) 0.3035(3) 0.0757(4) 0.0392(12) Uani 1 d . . H16A H 0.7420(46) 0.3360(6) 0.0274(6) 0.059 Uiso 1 calc R . H16B H 0.7057(37) 0.2711(12) 0.0538(12) 0.059 Uiso 1 calc R . H16C H 0.8840(11) 0.2918(17) 0.0736(8) 0.059 Uiso 1 calc R . C17 C 0.5923(7) 0.4409(2) 0.0932(4) 0.0430(13) Uani 1 d . . H17A H 0.6898(23) 0.4279(2) 0.0796(33) 0.065 Uiso 1 calc R . H17B H 0.6181(42) 0.4624(10) 0.1601(13) 0.065 Uiso 1 calc R . H17C H 0.5340(20) 0.4659(9) 0.0351(22) 0.065 Uiso 1 calc R . C18 C 0.4207(6) 0.3617(2) -0.0091(3) 0.0342(10) Uani 1 d . . H18A H 0.3651(38) 0.3261(9) -0.0024(5) 0.051 Uiso 1 calc R . H18B H 0.5058(7) 0.3530(15) -0.0405(13) 0.051 Uiso 1 calc R . H18C H 0.3467(34) 0.3889(7) -0.0547(10) 0.051 Uiso 1 calc R . C20 C 0.1636(5) 0.1087(2) 0.2049(3) 0.0252(8) Uani 1 d . . C21 C 0.0989(6) 0.0728(2) 0.2655(4) 0.0331(10) Uani 1 d . . H21 H 0.1659(6) 0.0505(2) 0.3210(4) 0.040 Uiso 1 calc R . C22 C -0.0657(7) 0.0693(2) 0.2450(4) 0.0372(12) Uani 1 d . . H22 H -0.1094(7) 0.0447(2) 0.2868(4) 0.045 Uiso 1 calc R . C22 C -0.1631(6) 0.1011(2) 0.1652(4) 0.0374(11) Uani 1 d . . H22A H -0.2742(6) 0.0978(2) 0.1503(4) 0.045 Uiso 1 calc R . C24 C -0.0994(6) 0.1380(3) 0.1065(4) 0.0413(12) Uani 1 d . . H24 H -0.1669(6) 0.1613(3) 0.0531(4) 0.050 Uiso 1 calc R . C25 C 0.0624(6) 0.1411(2) 0.1248(4) 0.0375(11) Uani 1 d . . H25 H 0.1047(6) 0.1657(2) 0.0822(4) 0.045 Uiso 1 calc R . C30 C 0.4396(5) 0.0635(2) 0.2761(4) 0.0289(9) Uani 1 d . . C31 C 0.4778(6) 0.0206(2) 0.2145(5) 0.0361(11) Uani 1 d . . H31 H 0.4385(6) 0.0230(2) 0.1394(5) 0.043 Uiso 1 calc R . C32 C 0.5724(7) -0.0259(2) 0.2601(6) 0.051(2) Uani 1 d . . H32 H 0.5957(7) -0.0553(2) 0.2167(6) 0.061 Uiso 1 calc R . C33 C 0.6321(7) -0.0289(3) 0.3697(6) 0.053(2) Uani 1 d . . H33 H 0.6983(7) -0.0602(3) 0.4013(6) 0.063 Uiso 1 calc R . C34 C 0.5963(6) 0.0130(2) 0.4327(5) 0.0468(14) Uani 1 d . . H34 H 0.6374(6) 0.0106(2) 0.5077(5) 0.056 Uiso 1 calc R . C35 C 0.4999(6) 0.0590(2) 0.3869(4) 0.0392(11) Uani 1 d . . H35 H 0.4747(6) 0.0877(2) 0.4309(4) 0.047 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh 0.01432(11) 0.01999(12) 0.01675(11) 0.0013(2) 0.00262(8) -0.0012(2) P 0.0168(4) 0.0245(5) 0.0185(4) 0.0007(4) 0.0045(4) -0.0035(4) Cl1 0.0167(4) 0.0364(6) 0.0421(6) 0.0107(5) 0.0048(4) 0.0040(4) Cl2 0.0318(5) 0.0313(5) 0.0184(4) -0.0018(4) 0.0046(4) -0.0007(4) C1 0.022(2) 0.023(2) 0.026(2) 0.005(2) 0.001(2) 0.000(2) C2 0.032(2) 0.028(2) 0.019(2) 0.007(2) -0.002(2) -0.004(2) C3 0.039(2) 0.028(2) 0.020(2) 0.001(2) 0.014(2) -0.005(2) C4 0.028(2) 0.026(2) 0.020(2) 0.0023(15) 0.009(2) -0.005(2) C5 0.029(2) 0.022(2) 0.020(2) 0.0039(14) 0.004(2) -0.005(2) C6 0.026(2) 0.023(2) 0.026(2) 0.000(2) 0.010(2) -0.006(2) C10 0.031(2) 0.025(2) 0.024(2) -0.004(2) 0.007(2) -0.009(2) C11 0.019(2) 0.039(2) 0.026(2) -0.004(2) 0.009(2) -0.006(2) C12 0.028(2) 0.025(2) 0.032(2) 0.009(2) 0.006(2) -0.003(2) C13 0.042(3) 0.039(3) 0.029(2) -0.008(2) 0.006(2) -0.017(2) C14 0.050(3) 0.030(2) 0.041(3) -0.009(2) 0.020(2) 0.000(2) C15 0.027(2) 0.066(4) 0.037(3) 0.012(3) 0.014(2) 0.012(2) C16 0.024(2) 0.067(4) 0.028(2) -0.008(2) 0.010(2) -0.002(2) C17 0.055(3) 0.034(3) 0.034(2) 0.008(2) 0.004(2) -0.017(2) C18 0.036(3) 0.035(2) 0.025(2) 0.010(2) -0.001(2) -0.006(2) C20 0.030(2) 0.020(2) 0.025(2) -0.0020(15) 0.008(2) -0.006(2) C21 0.037(3) 0.024(2) 0.041(3) 0.002(2) 0.015(2) 0.001(2) C22 0.044(3) 0.027(2) 0.048(3) -0.001(2) 0.025(3) -0.004(2) C22 0.026(2) 0.040(3) 0.046(3) -0.012(2) 0.011(2) -0.006(2) C24 0.029(2) 0.053(3) 0.038(3) 0.009(2) 0.005(2) -0.003(2) C25 0.031(2) 0.047(3) 0.033(2) 0.010(2) 0.006(2) -0.007(2) C30 0.026(2) 0.021(2) 0.039(2) 0.003(2) 0.009(2) -0.007(2) C31 0.034(3) 0.031(2) 0.050(3) 0.000(2) 0.022(2) -0.004(2) C32 0.040(3) 0.031(3) 0.097(5) 0.006(3) 0.042(3) 0.006(2) C33 0.033(3) 0.041(3) 0.088(5) 0.027(3) 0.024(3) 0.010(2) C34 0.032(3) 0.047(3) 0.056(3) 0.023(3) 0.005(2) -0.002(2) C35 0.037(3) 0.031(2) 0.042(3) 0.010(2) 0.001(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh C3 2.135(4) . ? Rh C1 2.155(4) . ? Rh C2 2.167(4) . ? Rh C4 2.237(4) . ? Rh C5 2.266(4) . ? Rh P 2.328(1) . ? Rh Cl1 2.382(1) . ? Rh Cl2 2.400(1) . ? P C11 1.844(4) . ? P C12 1.860(4) . ? P C10 1.870(4) . ? C1 C2 1.423(6) . ? C1 C5 1.457(6) . ? C2 C3 1.419(7) . ? C3 C4 1.444(6) . ? C4 C5 1.398(6) . ? C5 C6 1.504(6) . ? C6 C30 1.514(6) . ? C6 C20 1.526(6) . ? C10 C14 1.525(7) . ? C10 C13 1.529(6) . ? C11 C15 1.520(7) . ? C11 C16 1.531(6) . ? C12 C18 1.532(6) . ? C12 C17 1.535(6) . ? C20 C21 1.389(6) . ? C20 C25 1.391(6) . ? C21 C22 1.407(7) . ? C22 C22 1.367(8) . ? C22 C24 1.380(8) . ? C24 C25 1.386(7) . ? C30 C31 1.387(7) . ? C30 C35 1.405(7) . ? C31 C32 1.392(7) . ? C32 C33 1.39(1) . ? C33 C34 1.375(9) . ? C34 C35 1.392(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 Rh C1 64.5(2) . . ? C3 Rh C2 38.5(2) . . ? C1 Rh C2 38.4(2) . . ? C3 Rh C4 38.5(2) . . ? C1 Rh C4 63.1(2) . . ? C2 Rh C4 63.5(2) . . ? C3 Rh C5 63.2(2) . . ? C1 Rh C5 38.4(2) . . ? C2 Rh C5 63.4(2) . . ? C4 Rh C5 36.2(2) . . ? C3 Rh P 107.4(1) . . ? C1 Rh P 115.3(1) . . ? C2 Rh P 93.4(1) . . ? C4 Rh P 145.3(1) . . ? C5 Rh P 153.5(1) . . ? C3 Rh Cl1 99.6(1) . . ? C1 Rh Cl1 153(1) . . ? C2 Rh Cl1 136.5(1) . . ? C4 Rh Cl1 90.7(1) . . ? C5 Rh Cl1 115.7(1) . . ? P Rh Cl1 89.79(4) . . ? C3 Rh Cl2 152.9(1) . . ? C1 Rh Cl2 93.1(1) . . ? C2 Rh Cl2 128.4(1) . . ? C4 Rh Cl2 118.9(1) . . ? C5 Rh Cl2 89.9(1) . . ? P Rh Cl2 95.72(4) . . ? Cl1 Rh Cl2 94.30(4) . . ? C11 P C12 106.8(2) . . ? C11 P C10 105.0(2) . . ? C12 P C10 105.6(2) . . ? C11 P Rh 116.9(2) . . ? C12 P Rh 115.2(2) . . ? C10 P Rh 106.3(1) . . ? C2 C1 C5 108.2(4) . . ? C2 C1 Rh 71.2(2) . . ? C5 C1 Rh 74.9(2) . . ? C3 C2 C1 107.4(4) . . ? C3 C2 Rh 69.5(2) . . ? C1 C2 Rh 70.3(2) . . ? C2 C3 C4 108.2(4) . . ? C2 C3 Rh 72.0(3) . . ? C4 C3 Rh 74.6(2) . . ? C5 C4 C3 108.5(4) . . ? C5 C4 Rh 73.0(2) . . ? C3 C4 Rh 66.9(2) . . ? C4 C5 C1 107.3(4) . . ? C4 C5 C6 128.9(4) . . ? C1 C5 C6 123.8(4) . . ? C4 C5 Rh 70.8(2) . . ? C1 C5 Rh 66.7(2) . . ? C6 C5 Rh 127.7(3) . . ? C5 C6 C30 110.2(4) . . ? C5 C6 C20 111.1(4) . . ? C30 C6 C20 115.9(4) . . ? C14 C10 C13 112.1(4) . . ? C14 C10 P 110.3(3) . . ? C13 C10 P 117.3(3) . . ? C15 C11 C16 109.9(4) . . ? C15 C11 P 111.7(3) . . ? C16 C11 P 113.1(3) . . ? C18 C12 C17 110.1(4) . . ? C18 C12 P 114.2(3) . . ? C17 C12 P 114.1(3) . . ? C21 C20 C25 118.6(4) . . ? C21 C20 C6 122.2(4) . . ? C25 C20 C6 119.2(4) . . ? C20 C21 C22 120.1(5) . . ? C22 C22 C21 120.4(5) . . ? C22 C22 C24 119.7(5) . . ? C22 C24 C25 120.4(5) . . ? C24 C25 C20 120.7(5) . . ? C31 C30 C35 118.1(5) . . ? C31 C30 C6 120.7(4) . . ? C35 C30 C6 121.2(4) . . ? C30 C31 C32 121.5(5) . . ? C33 C32 C31 119.2(6) . . ? C34 C33 C32 120.5(5) . . ? C33 C34 C35 120.1(6) . . ? C34 C35 C30 120.5(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 Rh P C11 109.5(2) . . . . ? C1 Rh P C11 40.0(2) . . . . ? C2 Rh P C11 72.9(2) . . . . ? C4 Rh P C11 118.7(3) . . . . ? C5 Rh P C11 45.1(3) . . . . ? Cl1 Rh P C11 -150.5(2) . . . . ? Cl2 Rh P C11 -56.2(2) . . . . ? C3 Rh P C12 -123.8(2) . . . . ? C1 Rh P C12 166.7(2) . . . . ? C2 Rh P C12 -160.4(2) . . . . ? C4 Rh P C12 -114.6(3) . . . . ? C5 Rh P C12 171.8(3) . . . . ? Cl1 Rh P C12 -23.8(2) . . . . ? Cl2 Rh P C12 70.5(2) . . . . ? C3 Rh P C10 -7.3(2) . . . . ? C1 Rh P C10 -76.8(2) . . . . ? C2 Rh P C10 -43.9(2) . . . . ? C4 Rh P C10 1.9(3) . . . . ? C5 Rh P C10 -71.7(3) . . . . ? Cl1 Rh P C10 92.7(2) . . . . ? Cl2 Rh P C10 -173.0(2) . . . . ? C3 Rh C1 C2 -37.4(3) . . . . ? C2 Rh C1 C2 0.000(2) . . . . ? C4 Rh C1 C2 -80.5(3) . . . . ? C5 Rh C1 C2 -115.6(4) . . . . ? P Rh C1 C2 60.7(3) . . . . ? Cl1 Rh C1 C2 -95.6(3) . . . . ? Cl2 Rh C1 C2 158.6(3) . . . . ? C3 Rh C1 C5 78.2(3) . . . . ? C2 Rh C1 C5 115.6(4) . . . . ? C4 Rh C1 C5 35.2(2) . . . . ? C5 Rh C1 C5 0.0 . . . . ? P Rh C1 C5 176.4(2) . . . . ? Cl1 Rh C1 C5 20.0(4) . . . . ? Cl2 Rh C1 C5 -85.8(2) . . . . ? C5 C1 C2 C3 -6.5(5) . . . . ? Rh C1 C2 C3 59.9(3) . . . . ? C5 C1 C2 Rh -66.4(3) . . . . ? Rh C1 C2 Rh 0.0 . . . . ? C3 Rh C2 C3 0.000(2) . . . . ? C1 Rh C2 C3 -118.2(4) . . . . ? C4 Rh C2 C3 -38.9(2) . . . . ? C5 Rh C2 C3 -79.5(3) . . . . ? P Rh C2 C3 114.0(2) . . . . ? Cl1 Rh C2 C3 20.7(3) . . . . ? Cl2 Rh C2 C3 -146.0(2) . . . . ? C3 Rh C2 C1 118.2(4) . . . . ? C1 Rh C2 C1 0.000(1) . . . . ? C4 Rh C2 C1 79.3(3) . . . . ? C5 Rh C2 C1 38.7(3) . . . . ? P Rh C2 C1 -127.8(2) . . . . ? Cl1 Rh C2 C1 138.9(2) . . . . ? Cl2 Rh C2 C1 -27.7(3) . . . . ? C1 C2 C3 C4 6.0(5) . . . . ? Rh C2 C3 C4 66.4(3) . . . . ? C1 C2 C3 Rh -60.4(3) . . . . ? Rh C2 C3 Rh 0.0 . . . . ? C1 Rh C3 C2 37.3(2) . . . . ? C2 Rh C3 C2 0.000(2) . . . . ? C4 Rh C3 C2 115.5(4) . . . . ? C5 Rh C3 C2 80.3(3) . . . . ? P Rh C3 C2 -72.9(2) . . . . ? Cl1 Rh C3 C2 -165.7(2) . . . . ? Cl2 Rh C3 C2 74.4(4) . . . . ? C1 Rh C3 C4 -78.1(3) . . . . ? C2 Rh C3 C4 -115.5(4) . . . . ? C4 Rh C3 C4 0.0 . . . . ? C5 Rh C3 C4 -35.2(2) . . . . ? P Rh C3 C4 171.6(2) . . . . ? Cl1 Rh C3 C4 78.8(3) . . . . ? Cl2 Rh C3 C4 -41.1(5) . . . . ? C2 C3 C4 C5 -3.2(5) . . . . ? Rh C3 C4 C5 61.5(3) . . . . ? C2 C3 C4 Rh -64.6(3) . . . . ? Rh C3 C4 Rh 0.0 . . . . ? C3 Rh C4 C5 -119.4(4) . . . . ? C1 Rh C4 C5 -37.3(2) . . . . ? C2 Rh C4 C5 -80.5(3) . . . . ? C5 Rh C4 C5 0.000(1) . . . . ? P Rh C4 C5 -133.5(2) . . . . ? Cl1 Rh C4 C5 135.9(2) . . . . ? Cl2 Rh C4 C5 40.6(3) . . . . ? C3 Rh C4 C3 0.0 . . . . ? C1 Rh C4 C3 82.1(3) . . . . ? C2 Rh C4 C3 38.9(3) . . . . ? C5 Rh C4 C3 119.4(4) . . . . ? P Rh C4 C3 -14.1(4) . . . . ? Cl1 Rh C4 C3 -104.7(3) . . . . ? Cl2 Rh C4 C3 160.0(2) . . . . ? C3 C4 C5 C1 -0.9(4) . . . . ? Rh C4 C5 C1 56.8(3) . . . . ? C3 C4 C5 C6 178.8(4) . . . . ? Rh C4 C5 C6 -123.5(4) . . . . ? C3 C4 C5 Rh -57.7(3) . . . . ? Rh C4 C5 Rh 0.0 . . . . ? C2 C1 C5 C4 4.6(5) . . . . ? Rh C1 C5 C4 -59.4(3) . . . . ? C2 C1 C5 C6 -175.1(4) . . . . ? Rh C1 C5 C6 120.9(4) . . . . ? C2 C1 C5 Rh 64.0(3) . . . . ? Rh C1 C5 Rh 0.0 . . . . ? C3 Rh C5 C4 37.4(3) . . . . ? C1 Rh C5 C4 119.5(4) . . . . ? C2 Rh C5 C4 80.7(3) . . . . ? C4 Rh C5 C4 0.000(1) . . . . ? P Rh C5 C4 112.1(3) . . . . ? Cl1 Rh C5 C4 -50.5(3) . . . . ? Cl2 Rh C5 C4 -145.2(2) . . . . ? C3 Rh C5 C1 -82.1(3) . . . . ? C1 Rh C5 C1 0.0 . . . . ? C2 Rh C5 C1 -38.8(3) . . . . ? C4 Rh C5 C1 -119.5(4) . . . . ? P Rh C5 C1 -7.4(4) . . . . ? Cl1 Rh C5 C1 -170.1(2) . . . . ? Cl2 Rh C5 C1 95.2(2) . . . . ? C3 Rh C5 C6 162.2(4) . . . . ? C1 Rh C5 C6 -115.7(5) . . . . ? C2 Rh C5 C6 -154.5(4) . . . . ? C4 Rh C5 C6 124.8(5) . . . . ? P Rh C5 C6 -123.1(3) . . . . ? Cl1 Rh C5 C6 74.3(4) . . . . ? Cl2 Rh C5 C6 -20.4(4) . . . . ? C4 C5 C6 C30 -128.6(4) . . . . ? C1 C5 C6 C30 51.1(5) . . . . ? Rh C5 C6 C30 136.3(3) . . . . ? C4 C5 C6 C20 1.3(6) . . . . ? C1 C5 C6 C20 -179.0(4) . . . . ? Rh C5 C6 C20 -93.8(4) . . . . ? C11 P C10 C14 159.7(3) . . . . ? C12 P C10 C14 47.0(4) . . . . ? Rh P C10 C14 -75.8(3) . . . . ? C11 P C10 C13 29.7(4) . . . . ? C12 P C10 C13 -83.0(4) . . . . ? Rh P C10 C13 154.2(3) . . . . ? C12 P C11 C15 -177.5(4) . . . . ? C10 P C11 C15 70.7(4) . . . . ? Rh P C11 C15 -46.7(4) . . . . ? C12 P C11 C16 -52.7(4) . . . . ? C10 P C11 C16 -164.5(4) . . . . ? Rh P C11 C16 78.0(4) . . . . ? C11 P C12 C18 78.8(4) . . . . ? C10 P C12 C18 -169.7(3) . . . . ? Rh P C12 C18 -52.9(4) . . . . ? C11 P C12 C17 -49.0(4) . . . . ? C10 P C12 C17 62.4(4) . . . . ? Rh P C12 C17 179.3(3) . . . . ? C5 C6 C20 C21 -100.4(5) . . . . ? C30 C6 C20 C21 26.4(6) . . . . ? C5 C6 C20 C25 78.2(5) . . . . ? C30 C6 C20 C25 -155.0(4) . . . . ? C25 C20 C21 C22 0.4(7) . . . . ? C6 C20 C21 C22 179.1(4) . . . . ? C20 C21 C22 C22 0.2(8) . . . . ? C21 C22 C22 C24 -1.7(8) . . . . ? C22 C22 C24 C25 2.8(8) . . . . ? C22 C24 C25 C20 -2.2(9) . . . . ? C21 C20 C25 C24 0.6(8) . . . . ? C6 C20 C25 C24 -178.2(5) . . . . ? C5 C6 C30 C31 -140.9(4) . . . . ? C20 C6 C30 C31 91.8(5) . . . . ? C5 C6 C30 C35 36.6(6) . . . . ? C20 C6 C30 C35 -90.7(5) . . . . ? C35 C30 C31 C32 0.3(7) . . . . ? C6 C30 C31 C32 177.9(4) . . . . ? C30 C31 C32 C33 -1.2(8) . . . . ? C31 C32 C33 C34 1.1(8) . . . . ? C32 C33 C34 C35 -0.2(8) . . . . ? C33 C34 C35 C30 -0.6(8) . . . . ? C31 C30 C35 C34 0.6(7) . . . . ? C6 C30 C35 C34 -177.0(4) . . . . ? _refine_diff_density_max 0.673 _refine_diff_density_min -0.813 _refine_diff_density_rms 0.079