# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1645 #============================================================================== data_global #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author ; Prof. A. Guy Orpen, School of Chemistry, Cantocks Close, University of Bristol. Bristol. BS8 1TS. ; _publ_contact_author_phone '0117 928 7648' _publ_contact_author_fax '0117 929 0509' _publ_contact_author_email Guy.Orpen@bris.ac.uk _publ_requested_journal 'Chem. Commun.' _publ_requested_coeditor_name ? _publ_contact_letter ; ; data_12 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C29.50 H22 F2 I3 O P2 Rh' _chemical_formula_weight 976.02 _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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 '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' -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.850(3) _cell_length_b 15.338(4) _cell_length_c 20.992(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6069.0(23) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description disks _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.136 _exptl_crystal_density_method ? _exptl_crystal_F_000 3672 _exptl_absorpt_coefficient_mu 3.755 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.3001 _exptl_absorpt_correction_T_max 0.8149 _exptl_absorpt_process_details ? _exptl_special_details ; G. M. Sheldrick. SADABS: A program for absorption correction with the Siemens SMART system; University of G\"ottingen: Germany, 1996. ; _diffrn_ambient_temperature 173(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33277 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6885 _reflns_number_observed 5701 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 14 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^)+(0.0288P)^2^+28.1604P] 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_number_reflns 6871 _refine_ls_number_parameters 355 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_obs 0.0382 _refine_ls_wR_factor_all 0.0981 _refine_ls_wR_factor_obs 0.0854 _refine_ls_goodness_of_fit_all 1.165 _refine_ls_goodness_of_fit_obs 1.132 _refine_ls_restrained_S_all 1.177 _refine_ls_restrained_S_obs 1.132 _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 Rh1 Rh 0.83086(2) 0.10299(3) 0.59027(2) 0.02746(10) Uani 1 d . . I1 I 0.86359(2) -0.00971(3) 0.68678(2) 0.03993(10) Uani 1 d . . I2 I 0.87547(2) -0.01781(3) 0.50359(2) 0.04405(11) Uani 1 d . . I3 I 0.69762(2) 0.04202(2) 0.58096(2) 0.03375(9) Uani 1 d . . C3 C 0.9269(3) 0.1358(4) 0.5973(2) 0.0375(13) Uani 1 d . . O3 O 0.9851(2) 0.1522(4) 0.6010(2) 0.0573(13) Uani 1 d . . P1 P 0.80665(8) 0.20669(10) 0.51178(7) 0.0336(3) Uani 1 d . . C1 C 0.7686(3) 0.3006(4) 0.5540(3) 0.0423(14) Uani 1 d . . H1A H 0.8072(3) 0.3409(4) 0.5663(3) 0.051 Uiso 1 calc R . H1B H 0.7362(3) 0.3323(4) 0.5249(3) 0.051 Uiso 1 calc R . C2 C 0.7278(3) 0.2731(4) 0.6134(3) 0.0382(13) Uani 1 d . . H2A H 0.6845(3) 0.2407(4) 0.6011(3) 0.046 Uiso 1 calc R . H2B H 0.7132(3) 0.3253(4) 0.6379(3) 0.046 Uiso 1 calc R . P2 P 0.78459(8) 0.20430(10) 0.66231(6) 0.0318(3) Uani 1 d . . C10 C 0.7444(3) 0.1795(4) 0.4493(3) 0.0382(13) Uani 1 d . . C11 C 0.6731(3) 0.2010(5) 0.4542(3) 0.048(2) Uani 1 d . . H11A H 0.6562(3) 0.2317(5) 0.4905(3) 0.058 Uiso 1 calc R . C12 C 0.6267(4) 0.1775(6) 0.4058(4) 0.058(2) Uani 1 d . . H12A H 0.5780(4) 0.1923(6) 0.4095(4) 0.070 Uiso 0.50 calc PR 1 F1 F 0.5570(5) 0.1906(8) 0.4134(4) 0.084(3) Uani 0.50 d P 2 C13 C 0.6491(4) 0.1338(5) 0.3534(3) 0.059(2) Uani 1 d . . H13A H 0.6163(4) 0.1177(5) 0.3211(3) 0.071 Uiso 1 calc R . C14 C 0.7202(4) 0.1128(5) 0.3474(3) 0.062(2) Uani 1 d . . H14A H 0.7364(4) 0.0828(5) 0.3106(3) 0.075 Uiso 1 calc R . C15 C 0.7676(4) 0.1353(5) 0.3944(3) 0.051(2) Uani 1 d . . H15A H 0.8164(4) 0.1209(5) 0.3898(3) 0.061 Uiso 1 calc R . C20 C 0.8818(4) 0.2547(5) 0.4686(3) 0.053(2) Uani 1 d . . C21 C 0.9429(4) 0.2075(6) 0.4540(3) 0.058(2) Uani 1 d . . H21A H 0.9471(4) 0.1480(6) 0.4661(3) 0.070 Uiso 1 calc R . C22 C 0.9968(5) 0.2484(10) 0.4220(5) 0.094(4) Uani 1 d . . H22A H 1.0381(5) 0.2161(10) 0.4110(5) 0.113 Uiso 0.50 calc PR 1 F2 F 1.0513(7) 0.2226(11) 0.4108(7) 0.115(5) Uani 0.50 d P 2 C23 C 0.9926(7) 0.3370(10) 0.4049(7) 0.126(5) Uani 1 d . . H23A H 1.0318(7) 0.3649(10) 0.3850(7) 0.152 Uiso 1 calc R . C24 C 0.9340(8) 0.3806(11) 0.4166(7) 0.148(7) Uani 1 d . . H24A H 0.9301(8) 0.4393(11) 0.4025(7) 0.178 Uiso 1 calc R . C25 C 0.8761(5) 0.3415(7) 0.4501(6) 0.102(4) Uani 1 d . . H25A H 0.8345(5) 0.3741(7) 0.4596(6) 0.122 Uiso 1 calc R . C30 C 0.7303(3) 0.1706(4) 0.7292(3) 0.0395(13) Uani 1 d . . C31 C 0.6566(3) 0.1715(6) 0.7261(3) 0.056(2) Uani 1 d . . H31A H 0.6337(3) 0.1899(6) 0.6881(3) 0.068 Uiso 1 calc R . C32 C 0.6164(4) 0.1459(7) 0.7778(4) 0.073(3) Uani 1 d . . H32A H 0.5661(4) 0.1487(7) 0.7751(4) 0.087 Uiso 0.50 calc PR 2 F3 F 0.5482(6) 0.1290(14) 0.7677(6) 0.149(7) Uani 0.50 d P 1 C33 C 0.6466(4) 0.1168(5) 0.8324(3) 0.056(2) Uani 1 d . . H33A H 0.6180(4) 0.0982(5) 0.8671(3) 0.067 Uiso 1 calc R . C34 C 0.7189(4) 0.1147(5) 0.8369(3) 0.057(2) Uani 1 d . . H34A H 0.7407(4) 0.0944(5) 0.8749(3) 0.068 Uiso 1 calc R . C35 C 0.7610(4) 0.1422(5) 0.7861(3) 0.050(2) Uani 1 d . . H35A H 0.8112(4) 0.1416(5) 0.7902(3) 0.060 Uiso 1 calc R . C40 C 0.8496(3) 0.2775(4) 0.6982(3) 0.0385(13) Uani 1 d . . C41 C 0.9115(4) 0.2439(6) 0.7267(4) 0.062(2) Uani 1 d . . H41A H 0.9218(4) 0.1832(6) 0.7255(4) 0.075 Uiso 1 calc R . C42 C 0.9573(4) 0.3023(7) 0.7566(4) 0.075(3) Uani 1 d . . H42A H 0.9996(4) 0.2810(7) 0.7756(4) 0.090 Uiso 0.50 calc PR 2 F4 F 1.0221(7) 0.2747(12) 0.7749(9) 0.162(8) Uani 0.50 d P 1 C43 C 0.9426(5) 0.3899(6) 0.7594(4) 0.076(3) Uani 1 d . . H43A H 0.9749(5) 0.4286(6) 0.7797(4) 0.091 Uiso 1 calc R . C44 C 0.8834(5) 0.4206(6) 0.7337(5) 0.083(3) Uani 1 d . . H44A H 0.8733(5) 0.4812(6) 0.7361(5) 0.099 Uiso 1 calc R . C45 C 0.8358(4) 0.3651(5) 0.7033(4) 0.059(2) Uani 1 d . . H45A H 0.7933(4) 0.3881(5) 0.6859(4) 0.071 Uiso 1 calc R . C50 C 1.0021(9) 0.4567(12) 0.5242(8) 0.156(6) Uiso 1 d D . C51 C 0.9713(8) 0.4262(12) 0.5845(7) 0.130(5) Uiso 1 d D . C52 C 0.9671(52) 0.4117(71) 0.6565(22) 0.473(56) Uiso 0.50 d PD . 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 0.0288(2) 0.0274(2) 0.0263(2) -0.0025(2) -0.00215(15) 0.0008(2) I1 0.0440(2) 0.0370(2) 0.0387(2) 0.0057(2) -0.0066(2) 0.0055(2) I2 0.0444(2) 0.0448(2) 0.0430(2) -0.0139(2) 0.0080(2) 0.0038(2) I3 0.0314(2) 0.0327(2) 0.0372(2) -0.00473(14) -0.00140(13) -0.00014(14) C3 0.039(3) 0.046(4) 0.028(3) -0.004(2) -0.006(2) -0.001(3) O3 0.033(2) 0.083(4) 0.056(3) -0.005(3) -0.005(2) -0.007(2) P1 0.0391(7) 0.0322(8) 0.0297(6) 0.0004(6) -0.0043(6) -0.0023(6) C1 0.061(4) 0.026(3) 0.040(3) -0.001(2) -0.014(3) -0.002(3) C2 0.047(3) 0.036(3) 0.032(3) -0.013(2) -0.009(2) 0.011(3) P2 0.0375(7) 0.0298(8) 0.0281(6) -0.0056(5) -0.0048(5) 0.0033(6) C10 0.046(3) 0.037(3) 0.031(3) 0.002(2) -0.006(2) 0.005(3) C11 0.049(3) 0.056(4) 0.039(3) -0.002(3) -0.008(3) 0.015(3) C12 0.051(4) 0.063(5) 0.060(4) -0.008(4) -0.024(3) 0.013(4) F1 0.054(5) 0.121(10) 0.076(6) -0.033(6) -0.032(4) 0.031(5) C13 0.078(5) 0.055(5) 0.045(4) -0.010(3) -0.030(3) 0.011(4) C14 0.085(5) 0.064(5) 0.038(3) -0.018(3) -0.020(3) 0.023(4) C15 0.055(4) 0.060(5) 0.037(3) -0.013(3) -0.003(3) 0.014(3) C20 0.056(4) 0.056(4) 0.048(4) 0.019(3) -0.005(3) -0.012(3) C21 0.056(4) 0.069(5) 0.048(4) 0.007(4) 0.008(3) -0.010(4) C22 0.055(5) 0.147(12) 0.080(6) 0.022(7) 0.024(5) -0.016(6) F2 0.092(9) 0.126(13) 0.128(11) 0.018(9) 0.028(8) 0.004(8) C23 0.091(8) 0.129(12) 0.158(12) 0.069(10) 0.043(8) -0.017(8) C24 0.112(10) 0.134(13) 0.198(15) 0.086(11) 0.059(10) -0.012(9) C25 0.078(6) 0.084(8) 0.143(10) 0.068(7) 0.017(6) 0.003(5) C30 0.045(3) 0.044(4) 0.030(3) -0.011(2) 0.002(2) 0.004(3) C31 0.044(3) 0.090(6) 0.034(3) -0.007(3) 0.004(3) 0.004(4) C32 0.052(4) 0.116(8) 0.051(4) -0.007(5) 0.014(3) 0.001(5) F3 0.067(7) 0.299(24) 0.080(8) 0.008(11) 0.023(6) 0.003(10) C33 0.069(5) 0.058(5) 0.042(3) -0.002(3) 0.018(3) -0.003(4) C34 0.070(5) 0.063(5) 0.038(3) 0.005(3) 0.003(3) 0.006(4) C35 0.055(4) 0.052(4) 0.042(3) 0.005(3) -0.002(3) 0.009(3) C40 0.045(3) 0.038(3) 0.033(3) -0.011(2) -0.006(2) 0.000(3) C41 0.060(4) 0.060(5) 0.068(5) -0.022(4) -0.018(4) 0.005(4) C42 0.050(4) 0.091(7) 0.083(6) -0.030(5) -0.022(4) 0.000(4) F4 0.106(10) 0.172(17) 0.207(17) -0.098(14) -0.075(11) 0.029(10) C43 0.084(6) 0.063(6) 0.080(6) -0.030(5) -0.015(5) -0.010(5) C44 0.101(7) 0.055(5) 0.092(7) -0.018(5) -0.028(6) -0.011(5) C45 0.068(5) 0.050(4) 0.059(4) -0.008(3) -0.020(4) -0.003(4) _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 C3 1.885(6) . ? Rh1 P1 2.335(2) . ? Rh1 P2 2.3370(15) . ? Rh1 I3 2.6869(6) . ? Rh1 I2 2.7296(7) . ? Rh1 I1 2.7337(7) . ? C3 O3 1.128(7) . ? P1 C10 1.809(6) . ? P1 C20 1.837(7) . ? P1 C1 1.837(6) . ? C1 C2 1.525(9) . ? C2 P2 1.820(6) . ? P2 C30 1.813(6) . ? P2 C40 1.825(6) . ? C10 C11 1.387(8) . ? C10 C15 1.406(8) . ? C11 C12 1.388(9) . ? C12 F1 1.340(11) . ? C12 C13 1.355(10) . ? C13 C14 1.384(11) . ? C14 C15 1.376(9) . ? C20 C25 1.390(12) . ? C20 C21 1.393(11) . ? C21 C22 1.371(11) . ? C22 F2 1.13(2) . ? C22 C23 1.41(2) . ? C23 C24 1.31(2) . ? C24 C25 1.432(14) . ? C30 C31 1.391(9) . ? C30 C35 1.396(8) . ? C31 C32 1.381(10) . ? C32 F3 1.328(14) . ? C32 C33 1.356(11) . ? C33 C34 1.366(10) . ? C34 C35 1.394(9) . ? C40 C45 1.372(10) . ? C40 C41 1.409(9) . ? C41 C42 1.393(11) . ? C42 F4 1.349(15) . ? C42 C43 1.374(13) . ? C43 C44 1.325(13) . ? C44 C45 1.391(11) . ? C50 C51 1.47(2) . ? C50 C50 1.68(3) 5_766 ? C51 C52 1.53(4) . ? 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 Rh1 P1 93.5(2) . . ? C3 Rh1 P2 97.5(2) . . ? P1 Rh1 P2 86.03(6) . . ? C3 Rh1 I3 175.1(2) . . ? P1 Rh1 I3 90.18(4) . . ? P2 Rh1 I3 85.97(4) . . ? C3 Rh1 I2 86.4(2) . . ? P1 Rh1 I2 93.00(4) . . ? P2 Rh1 I2 176.03(4) . . ? I3 Rh1 I2 90.19(2) . . ? C3 Rh1 I1 83.9(2) . . ? P1 Rh1 I1 176.13(4) . . ? P2 Rh1 I1 91.44(4) . . ? I3 Rh1 I1 92.57(2) . . ? I2 Rh1 I1 89.73(3) . . ? O3 C3 Rh1 177.4(6) . . ? C10 P1 C20 103.6(3) . . ? C10 P1 C1 106.1(3) . . ? C20 P1 C1 103.0(3) . . ? C10 P1 Rh1 118.8(2) . . ? C20 P1 Rh1 118.1(2) . . ? C1 P1 Rh1 105.7(2) . . ? C2 C1 P1 112.0(4) . . ? C1 C2 P2 109.0(4) . . ? C30 P2 C2 105.7(3) . . ? C30 P2 C40 103.5(3) . . ? C2 P2 C40 105.7(3) . . ? C30 P2 Rh1 121.5(2) . . ? C2 P2 Rh1 103.9(2) . . ? C40 P2 Rh1 115.2(2) . . ? C11 C10 C15 118.5(6) . . ? C11 C10 P1 121.3(5) . . ? C15 C10 P1 120.2(5) . . ? C10 C11 C12 119.6(6) . . ? F1 C12 C13 118.4(7) . . ? F1 C12 C11 119.5(7) . . ? C13 C12 C11 121.8(7) . . ? C12 C13 C14 119.4(6) . . ? C15 C14 C13 120.4(6) . . ? C14 C15 C10 120.4(6) . . ? C25 C20 C21 120.1(7) . . ? C25 C20 P1 117.4(7) . . ? C21 C20 P1 122.5(6) . . ? C22 C21 C20 118.8(9) . . ? F2 C22 C21 128.1(15) . . ? F2 C22 C23 109.8(12) . . ? C21 C22 C23 121.7(11) . . ? C24 C23 C22 119.4(11) . . ? C23 C24 C25 121.3(13) . . ? C20 C25 C24 118.6(11) . . ? C31 C30 C35 117.2(6) . . ? C31 C30 P2 121.6(5) . . ? C35 C30 P2 121.2(5) . . ? C32 C31 C30 120.6(7) . . ? F3 C32 C33 118.6(10) . . ? F3 C32 C31 117.4(9) . . ? C33 C32 C31 121.9(7) . . ? C32 C33 C34 119.0(7) . . ? C33 C34 C35 120.6(7) . . ? C34 C35 C30 120.8(6) . . ? C45 C40 C41 118.9(6) . . ? C45 C40 P2 120.5(5) . . ? C41 C40 P2 120.4(5) . . ? C42 C41 C40 117.9(8) . . ? F4 C42 C43 118.5(10) . . ? F4 C42 C41 119.1(11) . . ? C43 C42 C41 121.6(8) . . ? C44 C43 C42 119.9(8) . . ? C43 C44 C45 120.8(9) . . ? C40 C45 C44 120.8(8) . . ? C51 C50 C50 139.2(21) . 5_766 ? C50 C51 C52 156.6(42) . . ? _refine_diff_density_max 0.856 _refine_diff_density_min -1.052 _refine_diff_density_rms 0.148