# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global #============================================================================== _audit_creation_date ? _audit_creation_method SHELXL-97 _audit_update_record ; ? ; #========================================================================== # 1. Submission Details _journal_coden_Cambridge 182 _publ_contact_author_name 'Albrecht Salzer' _publ_contact_author_address ; Institut fuer Anorganische Chemie RWTH Aachen Prof.-Pirlet-Str.1 52074 Aachen Germany ; _publ_contact_author_email albrecht.salzer@ac.rwth-aachen.de _publ_contact_author_fax 0049-241-8092288 _publ_contact_author_phone 0049-241-8094666 _publ_requested_journal 'Chem. Commun.' _publ_requested_category ? _publ_requested_coeditor_name ? # 3. Title and Author List _publ_section_title ; Isolation and structural characterization of an optically active intermediate in the oxidative addition of methyl iodide on a rhodium(I) centre ; loop_ _publ_author_name _publ_author_address 'Doppiu, Angelino' ; Institut fuer Anorganische Chemie RWTH Aachen Prof.-Pirlet-Str.1 52074 Aachen Germany ; 'Englert, Ulli' ; Institut fuer Anorganische Chemie RWTH Aachen Prof.-Pirlet-Str.1 52074 Aachen Germany ; 'Salzer, Albrecht' ; Institut fuer Anorganische Chemie RWTH Aachen Prof.-Pirlet-Str.1 52074 Aachen Germany ; _publ_section_references ; Bruker (1999). SAINT+. Version 6.02. Bruker AXS Inc., Madison, Wisconson, USA. Bruker (2001). SMART. Version 5.624. Bruker AXS Inc., Madison, Wisconson, USA. Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany. Sheldrick, G. M. (1997). SHELXS-97. University of Gottingen, Germany. Sheldrick, G. M. (1997). SHELXL-97. University of Gottingen, Germany. Sheldrick, G. M. (1998). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconson, USA. Spek, A. L. (1990). Acta Cryst. A46, C-34. ; _publ_section_figure_captions ; ? ; _publ_section_table_legends ; ? ; _publ_section_acknowledgements ; Support from the DFG and the Fonds der Chemischen Industrie is gratefully acknowledged. ; #========================================================================== data_ad6 _database_code_depnum_ccdc_archive 'CCDC 242796' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 3·CH3NO2 _chemical_formula_moiety ? _chemical_formula_sum 'C29 H32 I N O2 P Rh' _chemical_formula_weight 687.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 .9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.913(3) _cell_length_b 14.436(4) _cell_length_c 19.885(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2845.6(13) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 8092 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 1.767 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (1996)' _exptl_absorpt_correction_T_min 0.7189 _exptl_absorpt_correction_T_max 0.8863 _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36867 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.44 _reflns_number_total 6499 _reflns_number_gt 5900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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^)+(0.0280P)^2^+3.2000P] 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 mixed _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(2) _refine_ls_number_reflns 6499 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_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_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.15464(4) -0.10984(2) 0.373220(17) 0.02717(9) Uani 1 d . . . P1 P 0.08488(12) 0.03697(7) 0.34640(6) 0.0209(2) Uani 1 d . . . C1 C -0.0135(4) 0.0732(3) 0.4237(2) 0.0200(9) Uani 1 d . . . H1 H -0.0974 0.0372 0.4239 0.024 Uiso 1 calc R . . C2 C 0.0702(5) 0.0413(3) 0.4848(2) 0.0271(10) Uani 1 d . . . H2A H 0.1478 0.0817 0.4900 0.032 Uiso 1 calc R . . H2B H 0.0158 0.0462 0.5252 0.032 Uiso 1 calc R . . C3 C 0.1180(5) -0.0587(3) 0.4764(2) 0.0251(9) Uani 1 d . . . C4 C 0.0342(5) -0.1365(3) 0.4635(2) 0.0293(11) Uani 1 d . . . H4 H -0.0596 -0.1362 0.4617 0.035 Uiso 1 calc R . . C5 C 0.1185(6) -0.2151(3) 0.4540(2) 0.0356(12) Uani 1 d . . . H5 H 0.0901 -0.2752 0.4451 0.043 Uiso 1 calc R . . C6 C 0.2540(6) -0.1848(4) 0.4607(3) 0.0400(13) Uani 1 d . . . H6 H 0.3297 -0.2222 0.4556 0.048 Uiso 1 calc R . . C7 C 0.2570(5) -0.0894(4) 0.4761(3) 0.0333(12) Uani 1 d . . . H7 H 0.3330 -0.0535 0.4844 0.040 Uiso 1 calc R . . C8 C -0.0528(5) 0.1748(3) 0.4248(2) 0.0235(9) Uani 1 d . . . C9 C -0.1804(5) 0.2012(3) 0.4025(2) 0.0285(10) Uani 1 d . . . H9 H -0.2422 0.1562 0.3896 0.034 Uiso 1 calc R . . C10 C -0.2163(6) 0.2949(3) 0.3993(3) 0.0372(12) Uani 1 d . . . H10 H -0.3004 0.3120 0.3828 0.045 Uiso 1 calc R . . C11 C -0.1264(5) 0.3619(3) 0.4208(2) 0.0345(11) Uani 1 d . . . H11 H -0.1500 0.4241 0.4183 0.041 Uiso 1 calc R . . C12 C -0.0022(6) 0.3368(3) 0.4457(3) 0.0368(12) Uani 1 d . . . H12 H 0.0570 0.3820 0.4613 0.044 Uiso 1 calc R . . C13 C 0.0346(5) 0.2439(3) 0.4477(3) 0.0319(11) Uani 1 d . . . H13 H 0.1188 0.2275 0.4646 0.038 Uiso 1 calc R . . C14 C 0.2136(5) 0.1275(3) 0.3380(2) 0.0273(10) Uani 1 d . . . C15 C 0.1782(5) 0.2135(3) 0.3105(2) 0.0325(11) Uani 1 d . . . H15 H 0.0934 0.2217 0.2914 0.039 Uiso 1 calc R . . C16 C 0.2691(6) 0.2862(4) 0.3118(3) 0.0440(14) Uani 1 d . . . H16 H 0.2459 0.3425 0.2922 0.053 Uiso 1 calc R . . C17 C 0.3926(7) 0.2763(4) 0.3417(3) 0.0588(19) Uani 1 d . . . H17 H 0.4526 0.3258 0.3430 0.071 Uiso 1 calc R . . C18 C 0.4274(6) 0.1918(5) 0.3699(4) 0.0603(19) Uani 1 d . . . H18 H 0.5113 0.1851 0.3903 0.072 Uiso 1 calc R . . C19 C 0.3392(5) 0.1168(4) 0.3682(3) 0.0413(12) Uani 1 d . . . H19 H 0.3639 0.0603 0.3871 0.050 Uiso 1 calc R . . C20 C -0.0227(4) 0.0503(3) 0.2722(2) 0.0222(9) Uani 1 d . . . C21 C -0.1627(5) 0.0387(3) 0.2759(2) 0.0265(10) Uani 1 d . . . H21 H -0.2045 0.0284 0.3171 0.032 Uiso 1 calc R . . C22 C -0.2392(5) 0.0429(4) 0.2164(3) 0.0332(11) Uani 1 d . . . H22 H -0.3326 0.0379 0.2187 0.040 Uiso 1 calc R . . C23 C -0.1776(5) 0.0544(4) 0.1538(2) 0.0349(11) Uani 1 d . . . H23 H -0.2297 0.0562 0.1150 0.042 Uiso 1 calc R . . C24 C -0.0399(5) 0.0631(4) 0.1498(2) 0.0337(11) Uani 1 d . . . H24 H 0.0015 0.0701 0.1081 0.040 Uiso 1 calc R . . C25 C 0.0382(5) 0.0613(3) 0.2086(2) 0.0276(10) Uani 1 d . . . H25 H 0.1314 0.0675 0.2057 0.033 Uiso 1 calc R . . C26 C 0.3104(7) -0.0944(4) 0.2927(3) 0.0555(18) Uani 1 d . . . H26A H 0.4024 -0.0769 0.3054 0.067 Uiso 1 d R . . H26B H 0.2650 -0.0656 0.2542 0.067 Uiso 1 d R . . C27 C 0.2889(8) -0.1871(5) 0.3008(3) 0.061(2) Uani 1 d . . . H27A H 0.3625 -0.2262 0.3174 0.074 Uiso 1 d R . . H27B H 0.2153 -0.2079 0.2715 0.074 Uiso 1 d R . . C28 C 0.0086(7) -0.1610(4) 0.3084(3) 0.0542(18) Uani 1 d . . . H28A H 0.0061 -0.2273 0.3115 0.081 Uiso 1 calc R . . H28B H 0.0299 -0.1431 0.2631 0.081 Uiso 1 calc R . . H28C H -0.0779 -0.1362 0.3206 0.081 Uiso 1 calc R . . O1 O 0.5306(4) 0.1275(3) 0.1161(2) 0.0554(11) Uani 1 d . . . C29 C 0.3316(8) 0.2028(4) 0.1414(4) 0.066(2) Uani 1 d . . . H29A H 0.2394 0.1894 0.1303 0.100 Uiso 1 calc R . . H29B H 0.3654 0.2499 0.1118 0.100 Uiso 1 calc R . . H29C H 0.3368 0.2242 0.1870 0.100 Uiso 1 calc R . . N1 N 0.4133(5) 0.1182(3) 0.1339(2) 0.0395(10) Uani 1 d . . . O2 O 0.3616(5) 0.0436(3) 0.1450(2) 0.0566(11) Uani 1 d . . . I1 I 0.36459(3) 0.443128(19) 0.058123(15) 0.02900(8) Uani 1 d . . . 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 Rh1 0.0403(2) 0.01793(15) 0.02325(16) 0.00238(13) 0.00222(17) 0.00416(16) P1 0.0259(6) 0.0155(5) 0.0212(5) 0.0009(4) 0.0001(4) 0.0015(4) C1 0.024(2) 0.017(2) 0.019(2) 0.0001(15) 0.0021(16) -0.0017(17) C2 0.036(3) 0.021(2) 0.024(2) 0.0005(17) 0.0011(19) 0.001(2) C3 0.032(2) 0.026(2) 0.0176(19) 0.0054(17) -0.0004(17) 0.004(2) C4 0.037(3) 0.024(2) 0.027(2) 0.0053(18) -0.002(2) 0.000(2) C5 0.054(4) 0.023(2) 0.029(3) 0.0105(19) 0.002(2) 0.002(2) C6 0.055(4) 0.031(3) 0.034(3) 0.011(2) 0.004(2) 0.017(3) C7 0.031(3) 0.035(3) 0.034(3) 0.008(2) -0.003(2) 0.000(2) C8 0.029(2) 0.019(2) 0.023(2) -0.0032(16) 0.0037(18) -0.0031(18) C9 0.027(3) 0.019(2) 0.040(3) -0.0050(19) 0.005(2) -0.0020(19) C10 0.037(3) 0.025(3) 0.050(3) -0.003(2) 0.006(2) 0.009(2) C11 0.041(3) 0.020(2) 0.042(3) -0.0012(19) 0.014(2) 0.003(2) C12 0.049(3) 0.023(2) 0.039(3) -0.011(2) 0.005(3) -0.006(2) C13 0.037(3) 0.027(2) 0.031(3) -0.004(2) -0.008(2) 0.001(2) C14 0.031(3) 0.023(2) 0.028(2) 0.0070(18) 0.002(2) -0.0003(19) C15 0.042(3) 0.023(2) 0.033(2) 0.005(2) -0.011(2) -0.006(2) C16 0.057(4) 0.031(3) 0.044(3) 0.015(3) -0.011(3) -0.014(3) C17 0.061(4) 0.043(3) 0.073(4) 0.025(3) -0.021(3) -0.024(3) C18 0.041(3) 0.061(4) 0.079(5) 0.025(4) -0.023(4) -0.019(3) C19 0.031(3) 0.040(3) 0.053(3) 0.017(3) -0.005(3) -0.005(2) C20 0.032(2) 0.0153(19) 0.019(2) 0.0014(17) -0.0026(17) 0.0037(19) C21 0.034(3) 0.021(2) 0.025(2) 0.0015(16) 0.0015(19) 0.0015(19) C22 0.033(3) 0.027(3) 0.040(3) 0.002(2) -0.007(2) 0.001(2) C23 0.047(3) 0.031(2) 0.027(2) -0.005(2) -0.010(2) 0.009(2) C24 0.053(3) 0.029(2) 0.020(2) 0.000(2) 0.000(2) 0.013(3) C25 0.034(3) 0.027(2) 0.021(2) -0.0001(19) 0.0009(18) 0.006(2) C26 0.069(4) 0.052(4) 0.045(3) 0.010(3) 0.022(3) 0.020(3) C27 0.087(5) 0.049(4) 0.049(4) 0.000(3) 0.020(4) 0.031(4) C28 0.077(5) 0.030(3) 0.056(4) 0.008(3) -0.026(4) -0.006(3) O1 0.040(2) 0.079(3) 0.047(2) 0.000(2) -0.0049(19) -0.004(2) C29 0.088(6) 0.045(3) 0.066(4) 0.013(3) 0.026(4) 0.006(4) N1 0.043(3) 0.044(3) 0.031(2) 0.006(2) 0.008(2) 0.000(2) O2 0.072(3) 0.040(2) 0.058(2) 0.0085(19) 0.024(2) -0.001(2) I1 0.03039(15) 0.02251(13) 0.03410(15) -0.00313(12) 0.00350(14) -0.00028(13) _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 Rh1 C28 2.074(6) . ? Rh1 C4 2.191(5) . ? Rh1 C3 2.210(4) . ? Rh1 C26 2.236(6) . ? Rh1 C5 2.240(4) . ? Rh1 C27 2.256(6) . ? Rh1 C6 2.273(5) . ? Rh1 P1 2.2923(12) . ? Rh1 C7 2.302(5) . ? P1 C20 1.830(4) . ? P1 C14 1.834(5) . ? P1 C1 1.894(4) . ? C1 C8 1.518(6) . ? C1 C2 1.542(6) . ? C1 H1 0.9800 . ? C2 C3 1.530(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.421(7) . ? C3 C7 1.447(7) . ? C4 C5 1.422(7) . ? C4 H4 0.9300 . ? C5 C6 1.419(8) . ? C5 H5 0.9300 . ? C6 C7 1.410(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.394(7) . ? C8 C13 1.397(7) . ? C9 C10 1.400(7) . ? C9 H9 0.9300 . ? C10 C11 1.383(7) . ? C10 H10 0.9300 . ? C11 C12 1.375(7) . ? C11 H11 0.9300 . ? C12 C13 1.391(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C19 1.391(7) . ? C14 C15 1.401(6) . ? C15 C16 1.385(7) . ? C15 H15 0.9300 . ? C16 C17 1.368(9) . ? C16 H16 0.9300 . ? C17 C18 1.386(9) . ? C17 H17 0.9300 . ? C18 C19 1.393(8) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.400(6) . ? C20 C25 1.411(6) . ? C21 C22 1.407(6) . ? C21 H21 0.9300 . ? C22 C23 1.395(7) . ? C22 H22 0.9300 . ? C23 C24 1.373(8) . ? C23 H23 0.9300 . ? C24 C25 1.404(6) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.365(9) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9801 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? O1 N1 1.224(6) . ? C29 N1 1.472(8) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? N1 O2 1.213(6) . ? 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 C28 Rh1 C4 93.8(2) . . ? C28 Rh1 C3 125.5(2) . . ? C4 Rh1 C3 37.67(17) . . ? C28 Rh1 C26 94.1(3) . . ? C4 Rh1 C26 168.9(2) . . ? C3 Rh1 C26 138.2(2) . . ? C28 Rh1 C5 95.3(2) . . ? C4 Rh1 C5 37.41(18) . . ? C3 Rh1 C5 62.27(17) . . ? C26 Rh1 C5 133.8(2) . . ? C28 Rh1 C27 80.7(3) . . ? C4 Rh1 C27 139.3(2) . . ? C3 Rh1 C27 148.7(2) . . ? C26 Rh1 C27 35.4(2) . . ? C5 Rh1 C27 102.5(2) . . ? C28 Rh1 C6 127.5(2) . . ? C4 Rh1 C6 61.7(2) . . ? C3 Rh1 C6 61.31(18) . . ? C26 Rh1 C6 107.2(2) . . ? C5 Rh1 C6 36.6(2) . . ? C27 Rh1 C6 89.9(2) . . ? C28 Rh1 P1 88.51(17) . . ? C4 Rh1 P1 100.89(13) . . ? C3 Rh1 P1 81.81(12) . . ? C26 Rh1 P1 87.09(16) . . ? C5 Rh1 P1 138.23(14) . . ? C27 Rh1 P1 119.11(17) . . ? C6 Rh1 P1 138.49(15) . . ? C28 Rh1 C7 154.8(2) . . ? C4 Rh1 C7 62.24(19) . . ? C3 Rh1 C7 37.34(17) . . ? C26 Rh1 C7 108.6(2) . . ? C5 Rh1 C7 61.31(18) . . ? C27 Rh1 C7 111.8(2) . . ? C6 Rh1 C7 35.90(19) . . ? P1 Rh1 C7 102.79(13) . . ? C20 P1 C14 104.9(2) . . ? C20 P1 C1 108.9(2) . . ? C14 P1 C1 103.6(2) . . ? C20 P1 Rh1 117.42(15) . . ? C14 P1 Rh1 118.04(16) . . ? C1 P1 Rh1 102.81(13) . . ? C8 C1 C2 114.4(3) . . ? C8 C1 P1 114.3(3) . . ? C2 C1 P1 106.3(3) . . ? C8 C1 H1 107.1 . . ? C2 C1 H1 107.1 . . ? P1 C1 H1 107.1 . . ? C3 C2 C1 111.2(3) . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C7 108.3(4) . . ? C4 C3 C2 125.8(4) . . ? C7 C3 C2 125.8(4) . . ? C4 C3 Rh1 70.4(3) . . ? C7 C3 Rh1 74.8(3) . . ? C2 C3 Rh1 117.9(3) . . ? C3 C4 C5 108.1(4) . . ? C3 C4 Rh1 71.9(3) . . ? C5 C4 Rh1 73.2(3) . . ? C3 C4 H4 126.0 . . ? C5 C4 H4 126.0 . . ? Rh1 C4 H4 120.7 . . ? C6 C5 C4 107.4(5) . . ? C6 C5 Rh1 72.9(3) . . ? C4 C5 Rh1 69.4(3) . . ? C6 C5 H5 126.3 . . ? C4 C5 H5 126.3 . . ? Rh1 C5 H5 123.0 . . ? C7 C6 C5 109.9(5) . . ? C7 C6 Rh1 73.2(3) . . ? C5 C6 Rh1 70.4(3) . . ? C7 C6 H6 125.0 . . ? C5 C6 H6 125.0 . . ? Rh1 C6 H6 122.9 . . ? C6 C7 C3 106.3(5) . . ? C6 C7 Rh1 70.9(3) . . ? C3 C7 Rh1 67.9(3) . . ? C6 C7 H7 126.9 . . ? C3 C7 H7 126.9 . . ? Rh1 C7 H7 125.9 . . ? C9 C8 C13 118.1(4) . . ? C9 C8 C1 119.5(4) . . ? C13 C8 C1 122.4(4) . . ? C8 C9 C10 120.6(5) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 119.8(5) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 120.3(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.9(5) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 121.1(5) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C19 C14 C15 119.4(5) . . ? C19 C14 P1 120.3(4) . . ? C15 C14 P1 119.5(4) . . ? C16 C15 C14 120.1(5) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 120.7(5) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 119.4(6) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 121.2(6) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C14 C19 C18 119.1(5) . . ? C14 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C21 C20 C25 119.0(4) . . ? C21 C20 P1 121.6(3) . . ? C25 C20 P1 119.0(3) . . ? C20 C21 C22 119.1(4) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C23 C22 C21 121.2(5) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 119.9(4) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 119.8(5) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C24 C25 C20 120.9(4) . . ? C24 C25 H25 119.6 . . ? C20 C25 H25 119.6 . . ? C27 C26 Rh1 73.1(4) . . ? C27 C26 H26A 111.5 . . ? Rh1 C26 H26A 119.0 . . ? C27 C26 H26B 115.9 . . ? Rh1 C26 H26B 106.6 . . ? H26A C26 H26B 121.3 . . ? C26 C27 Rh1 71.5(4) . . ? C26 C27 H27A 119.3 . . ? Rh1 C27 H27A 120.6 . . ? C26 C27 H27B 110.2 . . ? Rh1 C27 H27B 95.3 . . ? H27A C27 H27B 125.3 . . ? Rh1 C28 H28A 109.5 . . ? Rh1 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? Rh1 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N1 C29 H29A 109.5 . . ? N1 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N1 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O2 N1 O1 123.5(5) . . ? O2 N1 C29 119.1(5) . . ? O1 N1 C29 117.5(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 C28 Rh1 P1 C20 -14.8(3) . . . . ? C4 Rh1 P1 C20 -108.4(2) . . . . ? C3 Rh1 P1 C20 -141.0(2) . . . . ? C26 Rh1 P1 C20 79.5(3) . . . . ? C5 Rh1 P1 C20 -111.1(3) . . . . ? C27 Rh1 P1 C20 63.8(3) . . . . ? C6 Rh1 P1 C20 -167.6(3) . . . . ? C7 Rh1 P1 C20 -172.1(2) . . . . ? C28 Rh1 P1 C14 -142.0(3) . . . . ? C4 Rh1 P1 C14 124.5(2) . . . . ? C3 Rh1 P1 C14 91.8(2) . . . . ? C26 Rh1 P1 C14 -47.7(3) . . . . ? C5 Rh1 P1 C14 121.7(3) . . . . ? C27 Rh1 P1 C14 -63.4(3) . . . . ? C6 Rh1 P1 C14 65.2(3) . . . . ? C7 Rh1 P1 C14 60.7(2) . . . . ? C28 Rh1 P1 C1 104.8(3) . . . . ? C4 Rh1 P1 C1 11.2(2) . . . . ? C3 Rh1 P1 C1 -21.45(19) . . . . ? C26 Rh1 P1 C1 -161.0(2) . . . . ? C5 Rh1 P1 C1 8.5(3) . . . . ? C27 Rh1 P1 C1 -176.7(3) . . . . ? C6 Rh1 P1 C1 -48.0(3) . . . . ? C7 Rh1 P1 C1 -52.5(2) . . . . ? C20 P1 C1 C8 -64.4(4) . . . . ? C14 P1 C1 C8 46.8(4) . . . . ? Rh1 P1 C1 C8 170.3(3) . . . . ? C20 P1 C1 C2 168.4(3) . . . . ? C14 P1 C1 C2 -80.3(3) . . . . ? Rh1 P1 C1 C2 43.1(3) . . . . ? C8 C1 C2 C3 -174.0(4) . . . . ? P1 C1 C2 C3 -46.9(4) . . . . ? C1 C2 C3 C4 -55.1(6) . . . . ? C1 C2 C3 C7 121.0(5) . . . . ? C1 C2 C3 Rh1 30.0(5) . . . . ? C28 Rh1 C3 C4 37.7(4) . . . . ? C26 Rh1 C3 C4 -163.8(3) . . . . ? C5 Rh1 C3 C4 -38.0(3) . . . . ? C27 Rh1 C3 C4 -104.9(5) . . . . ? C6 Rh1 C3 C4 -79.8(3) . . . . ? P1 Rh1 C3 C4 119.9(3) . . . . ? C7 Rh1 C3 C4 -116.2(4) . . . . ? C28 Rh1 C3 C7 153.9(3) . . . . ? C4 Rh1 C3 C7 116.2(4) . . . . ? C26 Rh1 C3 C7 -47.6(4) . . . . ? C5 Rh1 C3 C7 78.2(3) . . . . ? C27 Rh1 C3 C7 11.3(6) . . . . ? C6 Rh1 C3 C7 36.4(3) . . . . ? P1 Rh1 C3 C7 -123.9(3) . . . . ? C28 Rh1 C3 C2 -83.3(4) . . . . ? C4 Rh1 C3 C2 -120.9(5) . . . . ? C26 Rh1 C3 C2 75.2(4) . . . . ? C5 Rh1 C3 C2 -159.0(4) . . . . ? C27 Rh1 C3 C2 134.2(5) . . . . ? C6 Rh1 C3 C2 159.2(4) . . . . ? P1 Rh1 C3 C2 -1.0(3) . . . . ? C7 Rh1 C3 C2 122.9(5) . . . . ? C7 C3 C4 C5 -1.1(5) . . . . ? C2 C3 C4 C5 175.6(4) . . . . ? Rh1 C3 C4 C5 64.7(3) . . . . ? C7 C3 C4 Rh1 -65.8(3) . . . . ? C2 C3 C4 Rh1 110.9(4) . . . . ? C28 Rh1 C4 C3 -150.1(3) . . . . ? C26 Rh1 C4 C3 74.4(12) . . . . ? C5 Rh1 C4 C3 116.1(4) . . . . ? C27 Rh1 C4 C3 129.7(4) . . . . ? C6 Rh1 C4 C3 78.8(3) . . . . ? P1 Rh1 C4 C3 -60.9(3) . . . . ? C7 Rh1 C4 C3 37.9(3) . . . . ? C28 Rh1 C4 C5 93.8(3) . . . . ? C3 Rh1 C4 C5 -116.1(4) . . . . ? C26 Rh1 C4 C5 -41.7(13) . . . . ? C27 Rh1 C4 C5 13.6(5) . . . . ? C6 Rh1 C4 C5 -37.3(3) . . . . ? P1 Rh1 C4 C5 -177.0(3) . . . . ? C7 Rh1 C4 C5 -78.2(3) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? Rh1 C4 C5 C6 63.5(3) . . . . ? C3 C4 C5 Rh1 -63.9(3) . . . . ? C28 Rh1 C5 C6 154.0(4) . . . . ? C4 Rh1 C5 C6 -116.7(4) . . . . ? C3 Rh1 C5 C6 -78.4(3) . . . . ? C26 Rh1 C5 C6 53.1(4) . . . . ? C27 Rh1 C5 C6 72.4(4) . . . . ? P1 Rh1 C5 C6 -112.2(3) . . . . ? C7 Rh1 C5 C6 -35.8(3) . . . . ? C28 Rh1 C5 C4 -89.3(3) . . . . ? C3 Rh1 C5 C4 38.3(3) . . . . ? C26 Rh1 C5 C4 169.8(4) . . . . ? C27 Rh1 C5 C4 -171.0(3) . . . . ? C6 Rh1 C5 C4 116.7(4) . . . . ? P1 Rh1 C5 C4 4.4(4) . . . . ? C7 Rh1 C5 C4 80.9(3) . . . . ? C4 C5 C6 C7 1.7(6) . . . . ? Rh1 C5 C6 C7 62.9(4) . . . . ? C4 C5 C6 Rh1 -61.2(3) . . . . ? C28 Rh1 C6 C7 -152.3(4) . . . . ? C4 Rh1 C6 C7 -80.9(3) . . . . ? C3 Rh1 C6 C7 -37.8(3) . . . . ? C26 Rh1 C6 C7 98.2(4) . . . . ? C5 Rh1 C6 C7 -119.0(5) . . . . ? C27 Rh1 C6 C7 129.5(4) . . . . ? P1 Rh1 C6 C7 -7.5(5) . . . . ? C28 Rh1 C6 C5 -33.3(4) . . . . ? C4 Rh1 C6 C5 38.1(3) . . . . ? C3 Rh1 C6 C5 81.2(3) . . . . ? C26 Rh1 C6 C5 -142.8(3) . . . . ? C27 Rh1 C6 C5 -111.5(4) . . . . ? P1 Rh1 C6 C5 111.5(3) . . . . ? C7 Rh1 C6 C5 119.0(5) . . . . ? C5 C6 C7 C3 -2.3(6) . . . . ? Rh1 C6 C7 C3 58.9(3) . . . . ? C5 C6 C7 Rh1 -61.2(4) . . . . ? C4 C3 C7 C6 2.1(5) . . . . ? C2 C3 C7 C6 -174.6(4) . . . . ? Rh1 C3 C7 C6 -60.9(4) . . . . ? C4 C3 C7 Rh1 62.9(3) . . . . ? C2 C3 C7 Rh1 -113.7(4) . . . . ? C28 Rh1 C7 C6 60.0(7) . . . . ? C4 Rh1 C7 C6 79.2(4) . . . . ? C3 Rh1 C7 C6 117.5(5) . . . . ? C26 Rh1 C7 C6 -93.9(4) . . . . ? C5 Rh1 C7 C6 36.5(3) . . . . ? C27 Rh1 C7 C6 -56.2(4) . . . . ? P1 Rh1 C7 C6 174.9(3) . . . . ? C28 Rh1 C7 C3 -57.4(6) . . . . ? C4 Rh1 C7 C3 -38.3(3) . . . . ? C26 Rh1 C7 C3 148.7(3) . . . . ? C5 Rh1 C7 C3 -81.0(3) . . . . ? C27 Rh1 C7 C3 -173.7(3) . . . . ? C6 Rh1 C7 C3 -117.5(5) . . . . ? P1 Rh1 C7 C3 57.4(3) . . . . ? C2 C1 C8 C9 -141.2(4) . . . . ? P1 C1 C8 C9 96.0(4) . . . . ? C2 C1 C8 C13 38.7(6) . . . . ? P1 C1 C8 C13 -84.1(5) . . . . ? C13 C8 C9 C10 3.9(7) . . . . ? C1 C8 C9 C10 -176.2(4) . . . . ? C8 C9 C10 C11 -2.4(8) . . . . ? C9 C10 C11 C12 -0.5(8) . . . . ? C10 C11 C12 C13 1.8(8) . . . . ? C11 C12 C13 C8 -0.2(8) . . . . ? C9 C8 C13 C12 -2.6(7) . . . . ? C1 C8 C13 C12 177.5(5) . . . . ? C20 P1 C14 C19 -154.3(4) . . . . ? C1 P1 C14 C19 91.5(4) . . . . ? Rh1 P1 C14 C19 -21.3(5) . . . . ? C20 P1 C14 C15 36.0(4) . . . . ? C1 P1 C14 C15 -78.2(4) . . . . ? Rh1 P1 C14 C15 169.0(3) . . . . ? C19 C14 C15 C16 1.8(8) . . . . ? P1 C14 C15 C16 171.6(4) . . . . ? C14 C15 C16 C17 -2.1(9) . . . . ? C15 C16 C17 C18 1.1(11) . . . . ? C16 C17 C18 C19 0.2(12) . . . . ? C15 C14 C19 C18 -0.6(8) . . . . ? P1 C14 C19 C18 -170.3(5) . . . . ? C17 C18 C19 C14 -0.4(11) . . . . ? C14 P1 C20 C21 -141.6(4) . . . . ? C1 P1 C20 C21 -31.2(4) . . . . ? Rh1 P1 C20 C21 85.1(4) . . . . ? C14 P1 C20 C25 46.2(4) . . . . ? C1 P1 C20 C25 156.7(4) . . . . ? Rh1 P1 C20 C25 -87.1(4) . . . . ? C25 C20 C21 C22 -3.1(7) . . . . ? P1 C20 C21 C22 -175.2(3) . . . . ? C20 C21 C22 C23 2.7(7) . . . . ? C21 C22 C23 C24 -0.8(8) . . . . ? C22 C23 C24 C25 -0.7(8) . . . . ? C23 C24 C25 C20 0.3(8) . . . . ? C21 C20 C25 C24 1.6(7) . . . . ? P1 C20 C25 C24 174.0(4) . . . . ? C28 Rh1 C26 C27 -67.6(5) . . . . ? C4 Rh1 C26 C27 67.8(14) . . . . ? C3 Rh1 C26 C27 129.8(5) . . . . ? C5 Rh1 C26 C27 33.8(6) . . . . ? C6 Rh1 C26 C27 63.8(5) . . . . ? P1 Rh1 C26 C27 -155.9(5) . . . . ? C7 Rh1 C26 C27 101.6(5) . . . . ? C28 Rh1 C27 C26 110.9(5) . . . . ? C4 Rh1 C27 C26 -164.1(4) . . . . ? C3 Rh1 C27 C26 -99.2(5) . . . . ? C5 Rh1 C27 C26 -155.7(5) . . . . ? C6 Rh1 C27 C26 -121.0(5) . . . . ? P1 Rh1 C27 C26 27.8(6) . . . . ? C7 Rh1 C27 C26 -91.9(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.238 _refine_diff_density_min -.994 _refine_diff_density_rms .106