# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1812 data_global # 1. SUBMISSION DETAILS _publ_contact_author ; Dr. Russell Hughes Department of Chemistry 6128 Burke Laboratory Hanover, New Hampshire 03755-3564 USA ; _publ_contact_author_phone '+603 646 2763' _publ_contact_author_fax '+603 646 3946' _publ_contact_author_email rph@dartmouth.edu.edu _publ_requested_journal 'J Chem Soc Dalton Trans' # 2. TITLE AND AUTHOR LIST _publ_section_title ; Syntheses and X-ray crystallographic studies of [Ir(___C5Me5)(L)(RF)I] (L = CO, PMe3; RF = CF2CF3, CF2CF2CF3, CF2C6F5, CF(CF3)2) complexes. Cone and solid angle steric parameters for perfluoroalkyl ligands. ; loop_ _publ_author_name _publ_author_address 'Hughes, Russell P.' ; Department of Chemistry 6128 Burke Laboratory Hanover, New Hampshire 03755-3564 USA ; 'Smith, Jeremy M.' ; Department of Chemistry 6128 Burke Laboratory Hanover, New Hampshire 03755-3564 USA ; 'Liable-Sands, Louise M.' ; University of Delaware Department of Chemistry and Biochemistry Academy Street Newark, DE 19716 U. S. A. ; 'Lam, Kin-Chung' ; University of Delaware Department of Chemistry and Biochemistry Academy Street Newark, DE 19716 U. S. A. ; 'Rheingold, Arnold L.' ; University of Delaware Department of Chemistry and Biochemistry Academy Street Newark, DE 19716 U. S. A. ; 'Concolino, Thomas E. ' ; University of Delaware Department of Chemistry and Biochemistry Academy Street Newark, DE 19716 U. S. A. ; 'Incarvito, Christopher ' ; University of Delaware Department of Chemistry and Biochemistry Academy Street Newark, DE 19716 U. S. A. ; # 3. Results data_rph105r _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 F5 I Ir O' _chemical_formula_weight 601.35 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.5211(2) _cell_length_b 17.4802(5) _cell_length_c 12.5964(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.4750(10) _cell_angle_gamma 90.00 _cell_volume 1645.49(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 10.034 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.638 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details DIFABS _exptl_special_details ; ? ; _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7178 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.91 _reflns_number_total 3608 _reflns_number_gt 3283 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 3608 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1554 _refine_ls_goodness_of_fit_ref 1.349 _refine_ls_restrained_S_all 1.349 _refine_ls_shift/su_max 0.529 _refine_ls_shift/su_mean 0.044 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.88578(4) 0.13861(2) 0.79032(2) 0.02160(17) Uani 1 1 d . . . I1 I 1.09811(11) 0.26700(4) 0.78164(6) 0.0335(2) Uani 0.83 1 d P . . O1 O 1.1297(10) 0.0763(5) 0.9809(6) 0.0424(18) Uani 1 1 d . . . C1 C 0.6375(11) 0.2036(6) 0.7159(7) 0.0271(19) Uani 1 1 d . . . C2 C 0.6465(12) 0.2079(6) 0.8333(7) 0.0286(19) Uani 1 1 d . . . C3 C 0.6334(12) 0.1313(6) 0.8720(7) 0.025(2) Uani 1 1 d . . . C4 C 0.6209(11) 0.0778(6) 0.7802(7) 0.0261(18) Uani 1 1 d . . . C5 C 0.6181(12) 0.1250(6) 0.6824(8) 0.0274(19) Uani 1 1 d . . . C6 C 0.6248(15) 0.2725(6) 0.6417(8) 0.038(2) Uani 1 1 d . . . H6A H 0.6851 0.2609 0.5785 0.057 Uiso 1 1 calc R . . H6B H 0.6824 0.3166 0.6792 0.057 Uiso 1 1 calc R . . H6C H 0.4987 0.2842 0.6195 0.057 Uiso 1 1 calc R . . C7 C 0.6519(16) 0.2818(7) 0.8990(10) 0.047(3) Uani 1 1 d . . . H7A H 0.5434 0.3117 0.8781 0.070 Uiso 1 1 calc R . . H7B H 0.7573 0.3119 0.8859 0.070 Uiso 1 1 calc R . . H7C H 0.6586 0.2691 0.9752 0.070 Uiso 1 1 calc R . . C8 C 0.6233(15) 0.1072(7) 0.9874(7) 0.038(2) Uani 1 1 d . . . H8A H 0.7433 0.1088 1.0268 0.057 Uiso 1 1 calc R . . H8B H 0.5760 0.0550 0.9889 0.057 Uiso 1 1 calc R . . H8C H 0.5442 0.1422 1.0207 0.057 Uiso 1 1 calc R . . C9 C 0.5755(14) -0.0065(6) 0.7833(8) 0.035(2) Uani 1 1 d . . . H9A H 0.4611 -0.0130 0.8126 0.053 Uiso 1 1 calc R . . H9B H 0.6698 -0.0335 0.8285 0.053 Uiso 1 1 calc R . . H9C H 0.5661 -0.0275 0.7107 0.053 Uiso 1 1 calc R . . C10 C 0.5793(13) 0.0963(7) 0.5687(7) 0.035(2) Uani 1 1 d . . . H10A H 0.4571 0.1105 0.5404 0.053 Uiso 1 1 calc R . . H10B H 0.5915 0.0405 0.5677 0.053 Uiso 1 1 calc R . . H10C H 0.6642 0.1193 0.5245 0.053 Uiso 1 1 calc R . . C11 C 1.0389(13) 0.0998(6) 0.9073(7) 0.0298(19) Uani 1 1 d . . . C12 C 1.0544(16) 0.0843(8) 0.6874(8) 0.033(3) Uani 0.83 1 d P . . C13I I 1.0223(5) 0.0022(2) 0.6831(3) 0.0390(9) Uani 0.17 1 d P . . F1 F 1.2359(8) 0.0979(4) 0.7198(6) 0.0362(16) Uani 0.83 1 d P . . F2 F 1.0237(10) 0.1104(5) 0.5851(5) 0.0371(16) Uani 0.83 1 d P . . F3 F 1.0688(12) -0.0369(4) 0.7748(7) 0.0455(19) Uani 0.83 1 d P . . F4 F 0.8807(11) -0.0269(4) 0.6336(7) 0.0467(19) Uani 0.83 1 d P . . F5 F 1.1610(11) -0.0312(5) 0.6180(7) 0.047(2) Uani 0.83 1 d P . . 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 Ir1 0.0188(2) 0.0282(3) 0.0178(2) 0.00194(11) 0.00182(15) 0.00169(12) I1 0.0356(4) 0.0276(4) 0.0372(4) 0.0008(3) 0.0039(3) -0.0122(3) O1 0.044(4) 0.047(5) 0.032(4) 0.004(3) -0.013(3) 0.012(4) C1 0.020(4) 0.028(5) 0.032(5) 0.008(4) -0.002(3) 0.005(3) C2 0.025(4) 0.031(5) 0.031(4) 0.003(4) 0.005(3) 0.013(4) C3 0.015(4) 0.045(6) 0.016(4) -0.006(3) 0.003(3) -0.001(3) C4 0.019(4) 0.029(5) 0.030(4) 0.001(4) -0.001(3) 0.008(3) C5 0.024(5) 0.032(5) 0.026(4) -0.001(4) 0.000(3) 0.010(4) C6 0.048(6) 0.035(6) 0.029(5) 0.011(4) -0.004(4) 0.001(5) C7 0.043(6) 0.048(7) 0.048(6) -0.025(5) -0.002(5) 0.011(5) C8 0.048(6) 0.050(6) 0.017(4) 0.008(4) 0.010(4) 0.005(5) C9 0.034(5) 0.035(6) 0.037(5) 0.008(4) -0.002(4) 0.007(4) C10 0.031(5) 0.058(7) 0.016(4) -0.009(4) -0.002(3) -0.003(5) C11 0.028(4) 0.037(5) 0.025(4) 0.002(4) 0.010(4) -0.001(4) C12 0.031(6) 0.054(8) 0.014(5) 0.008(5) 0.003(4) 0.005(5) C13I 0.0362(19) 0.038(2) 0.041(2) -0.0171(16) -0.0005(15) 0.0003(16) F1 0.018(3) 0.040(4) 0.051(4) -0.013(3) 0.009(3) -0.001(3) F2 0.054(4) 0.041(4) 0.019(3) 0.007(3) 0.014(3) -0.001(3) F3 0.058(5) 0.030(4) 0.048(4) -0.005(3) 0.008(4) 0.003(4) F4 0.052(5) 0.033(4) 0.056(5) -0.014(4) 0.008(4) 0.002(3) F5 0.041(4) 0.047(5) 0.054(5) -0.021(4) 0.021(4) 0.004(3) _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 Ir1 C11 1.891(10) . ? Ir1 C12 2.135(12) . ? Ir1 C4 2.249(9) . ? Ir1 C3 2.262(9) . ? Ir1 C2 2.284(9) . ? Ir1 C1 2.293(8) . ? Ir1 C5 2.311(9) . ? Ir1 I1 2.7638(8) . ? O1 C11 1.164(12) . ? C1 C5 1.440(14) . ? C1 C2 1.475(13) . ? C1 C6 1.521(13) . ? C2 C3 1.432(14) . ? C2 C7 1.532(14) . ? C3 C4 1.483(13) . ? C3 C8 1.524(12) . ? C4 C5 1.481(14) . ? C4 C9 1.513(14) . ? C5 C10 1.514(13) . ? C12 F2 1.362(12) . ? C12 F1 1.400(13) . ? C12 C13I 1.456(15) . ? C13I F4 1.277(9) . ? C13I F3 1.355(10) . ? C13I F5 1.514(8) . ? 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 C11 Ir1 C12 87.9(4) . . ? C11 Ir1 C4 109.4(4) . . ? C12 Ir1 C4 109.8(4) . . ? C11 Ir1 C3 95.4(4) . . ? C12 Ir1 C3 146.9(4) . . ? C4 Ir1 C3 38.4(3) . . ? C11 Ir1 C2 115.6(4) . . ? C12 Ir1 C2 156.5(4) . . ? C4 Ir1 C2 63.1(4) . . ? C3 Ir1 C2 36.7(3) . . ? C11 Ir1 C1 153.2(3) . . ? C12 Ir1 C1 118.9(4) . . ? C4 Ir1 C1 62.4(3) . . ? C3 Ir1 C1 61.8(3) . . ? C2 Ir1 C1 37.6(3) . . ? C11 Ir1 C5 146.6(4) . . ? C12 Ir1 C5 97.7(4) . . ? C4 Ir1 C5 37.9(3) . . ? C3 Ir1 C5 62.7(3) . . ? C2 Ir1 C5 62.4(3) . . ? C1 Ir1 C5 36.4(3) . . ? C11 Ir1 I1 91.0(3) . . ? C12 Ir1 I1 87.2(4) . . ? C4 Ir1 I1 153.4(2) . . ? C3 Ir1 I1 125.6(2) . . ? C2 Ir1 I1 93.0(3) . . ? C1 Ir1 I1 91.7(2) . . ? C5 Ir1 I1 122.0(3) . . ? C5 C1 C2 109.5(8) . . ? C5 C1 C6 125.3(9) . . ? C2 C1 C6 124.6(9) . . ? C5 C1 Ir1 72.4(5) . . ? C2 C1 Ir1 70.9(5) . . ? C6 C1 Ir1 129.5(7) . . ? C3 C2 C1 107.2(8) . . ? C3 C2 C7 127.1(9) . . ? C1 C2 C7 125.5(9) . . ? C3 C2 Ir1 70.8(5) . . ? C1 C2 Ir1 71.5(5) . . ? C7 C2 Ir1 127.0(7) . . ? C2 C3 C4 109.0(8) . . ? C2 C3 C8 126.6(9) . . ? C4 C3 C8 124.3(9) . . ? C2 C3 Ir1 72.5(5) . . ? C4 C3 Ir1 70.3(5) . . ? C8 C3 Ir1 125.7(7) . . ? C5 C4 C3 106.9(8) . . ? C5 C4 C9 125.6(9) . . ? C3 C4 C9 126.1(9) . . ? C5 C4 Ir1 73.3(5) . . ? C3 C4 Ir1 71.3(5) . . ? C9 C4 Ir1 131.3(6) . . ? C1 C5 C4 107.2(8) . . ? C1 C5 C10 126.6(9) . . ? C4 C5 C10 125.8(9) . . ? C1 C5 Ir1 71.1(5) . . ? C4 C5 Ir1 68.8(5) . . ? C10 C5 Ir1 130.8(7) . . ? O1 C11 Ir1 178.2(8) . . ? F2 C12 F1 105.9(9) . . ? F2 C12 C13I 106.5(9) . . ? F1 C12 C13I 109.2(9) . . ? F2 C12 Ir1 112.2(8) . . ? F1 C12 Ir1 112.0(8) . . ? C13I C12 Ir1 110.7(7) . . ? F4 C13I F3 109.7(6) . . ? F4 C13I C12 122.4(7) . . ? F3 C13I C12 116.1(6) . . ? F4 C13I F5 99.8(5) . . ? F3 C13I F5 98.0(5) . . ? C12 C13I F5 106.2(6) . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 2.965 _refine_diff_density_min -2.251 _refine_diff_density_rms 0.256 #===END data_rph21 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 F7 I Ir O' _chemical_formula_weight 699.40 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.373(4) _cell_length_b 10.850(3) _cell_length_c 15.330(6) _cell_angle_alpha 90.00 _cell_angle_beta 114.02(2) _cell_angle_gamma 90.00 _cell_volume 2031.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 12.5 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 8.159 _exptl_absorpt_correction_type N/A _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 P4' _diffrn_measurement_method wyckoff _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '<1.0' _diffrn_reflns_number 3921 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3921 _reflns_number_gt 2602 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P4' _computing_cell_refinement 'Siemens P4' _computing_data_reduction XDISK _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-90 4.2 (Sheldrick, 1990)' _computing_molecular_graphics XP _computing_publication_material XCIF _refine_special_details ; Refinement of F against ALL reflections greater than 4 sigma or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodness of fit S are based on F, conventional R-factors R are based on F. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0000P] 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 'idealized contributions' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0010(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3774 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.0683 _refine_ls_wR_factor_gt 0.0625 _refine_ls_goodness_of_fit_ref 1.34 _refine_ls_restrained_S_all 1.33 _refine_ls_shift/su_max 0.000 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir Ir 0.00223(4) 0.12098(4) 0.28014(3) 0.0385(2) Uani 1 1 d . . . I I -0.21625(8) 0.12382(10) 0.21464(8) 0.0739(3) Uani 1 1 d . . . O1 O -0.0081(11) -0.1411(9) 0.3266(8) 0.081(3) Uani 1 1 d . . . C1 C -0.0040(10) -0.0470(14) 0.3078(8) 0.046(3) Uani 1 1 d . . . C2 C -0.0044(11) 0.0835(14) 0.1400(10) 0.060(4) Uani 1 1 d . . . F1 F 0.0636(7) -0.1698(9) 0.1750(7) 0.083(3) Uani 1 1 d . . . F2 F -0.0556(10) -0.3591(8) 0.0819(8) 0.101(3) Uani 1 1 d . . . F3 F -0.2605(8) -0.3245(9) -0.0551(7) 0.092(3) Uani 1 1 d . . . F4 F -0.3383(9) -0.0947(9) -0.0996(6) 0.101(3) Uani 1 1 d . . . F5 F -0.2212(8) 0.0970(7) -0.0136(6) 0.084(3) Uani 1 1 d . . . F6 F 0.1013(7) 0.0619(9) 0.1507(6) 0.075(3) Uani 1 1 d . . . F7 F -0.0363(8) 0.1831(8) 0.0864(5) 0.077(3) Uani 1 1 d . . . C11 C 0.0239(11) 0.2595(12) 0.3953(9) 0.052(3) Uani 1 1 d . . . C12 C 0.1118(10) 0.1789(11) 0.4306(8) 0.045(3) Uani 1 1 d . . . C13 C 0.1691(10) 0.1854(11) 0.3665(8) 0.044(3) Uani 1 1 d . . . C14 C 0.1151(10) 0.2807(11) 0.2950(9) 0.048(3) Uani 1 1 d . . . C15 C 0.0222(11) 0.3224(11) 0.3118(10) 0.049(3) Uani 1 1 d . . . C16 C -0.0551(13) 0.2900(14) 0.4407(11) 0.073(5) Uani 1 1 d . . . H16A H -0.0236 0.3528 0.4882 0.080 Uiso 1 1 d R . . H16B H -0.1227 0.3194 0.3925 0.080 Uiso 1 1 d R . . H16C H -0.0690 0.2176 0.4702 0.080 Uiso 1 1 d R . . C17 C 0.1464(13) 0.1016(14) 0.5167(10) 0.072(4) Uani 1 1 d . . . H17A H 0.1926 0.1478 0.5718 0.080 Uiso 1 1 d R . . H17B H 0.0830 0.0734 0.5253 0.080 Uiso 1 1 d R . . H17C H 0.1861 0.0320 0.5085 0.080 Uiso 1 1 d R . . C18 C 0.2745(12) 0.1245(13) 0.3836(12) 0.070(4) Uani 1 1 d . . . H20A H 0.3338 0.1762 0.4234 0.080 Uiso 1 1 d R . . H20B H 0.2774 0.0475 0.4155 0.080 Uiso 1 1 d R . . H20C H 0.2806 0.1095 0.3243 0.080 Uiso 1 1 d R . . C19 C 0.1598(13) 0.3320(14) 0.2299(12) 0.076(5) Uani 1 1 d . . . H21A H 0.2073 0.3994 0.2614 0.080 Uiso 1 1 d R . . H21B H 0.2000 0.2715 0.2116 0.080 Uiso 1 1 d R . . H21C H 0.0999 0.3618 0.1741 0.080 Uiso 1 1 d R . . C20 C -0.0526(12) 0.4227(15) 0.2580(13) 0.086(6) Uani 1 1 d . . . H22A H -0.0222 0.5001 0.2871 0.080 Uiso 1 1 d R . . H22B H -0.0632 0.4236 0.1922 0.080 Uiso 1 1 d R . . H22C H -0.1216 0.4099 0.2620 0.080 Uiso 1 1 d R . . C31 C -0.0357(11) -0.1448(12) 0.1077(10) 0.053(3) Uani 1 1 d . . . C32 C -0.0957(13) -0.2438(13) 0.0605(11) 0.061(4) Uani 1 1 d . . . C33 C -0.2000(13) -0.2287(13) -0.0086(11) 0.061(4) Uani 1 1 d . . . C34 C -0.2390(12) -0.1134(13) -0.0313(9) 0.059(4) Uani 1 1 d . . . C35 C -0.1805(13) -0.0142(13) 0.0158(9) 0.061(4) Uani 1 1 d . . . C36 C -0.0753(10) -0.0254(10) 0.0866(8) 0.044(3) Uani 1 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 Ir 0.0421(3) 0.0400(3) 0.0379(3) -0.0011(2) 0.0208(2) -0.0057(2) I 0.0462(5) 0.0877(8) 0.0882(7) -0.0022(6) 0.0277(5) -0.0081(5) O1 0.129(10) 0.053(7) 0.083(8) -0.009(6) 0.065(8) -0.026(6) C1 0.058(8) 0.058(8) 0.028(6) -0.003(6) 0.025(6) -0.002(6) C2 0.054(8) 0.076(10) 0.052(8) -0.023(7) 0.025(7) -0.009(7) F1 0.069(6) 0.085(6) 0.092(7) 0.000(5) 0.031(5) 0.030(5) F2 0.127(9) 0.049(5) 0.125(9) -0.013(5) 0.049(7) 0.017(5) F3 0.104(7) 0.075(6) 0.101(7) -0.040(6) 0.046(6) -0.040(6) F4 0.092(7) 0.110(8) 0.063(6) 0.002(5) -0.006(5) -0.029(6) F5 0.100(7) 0.056(5) 0.057(5) 0.013(4) -0.006(5) 0.003(5) F6 0.069(5) 0.101(6) 0.081(6) -0.031(5) 0.056(5) -0.036(5) F7 0.127(8) 0.058(5) 0.045(4) 0.007(4) 0.033(5) -0.038(5) C11 0.062(8) 0.044(7) 0.051(8) -0.006(6) 0.023(7) 0.006(6) C12 0.052(7) 0.042(6) 0.040(6) -0.012(5) 0.019(6) -0.016(6) C13 0.051(7) 0.038(6) 0.045(7) -0.021(6) 0.021(6) -0.018(6) C14 0.056(8) 0.045(7) 0.046(7) -0.005(6) 0.025(6) -0.010(6) C15 0.070(9) 0.025(6) 0.065(8) -0.003(6) 0.040(7) -0.003(6) C16 0.100(12) 0.073(10) 0.073(10) -0.009(8) 0.063(10) 0.017(9) C17 0.075(10) 0.090(12) 0.048(8) 0.003(8) 0.021(7) 0.003(9) C18 0.068(9) 0.058(9) 0.084(11) -0.009(8) 0.030(8) 0.004(8) C19 0.081(11) 0.074(10) 0.080(11) 0.011(9) 0.039(9) -0.031(9) C20 0.053(9) 0.066(10) 0.122(15) 0.006(10) 0.019(10) 0.005(8) C31 0.054(7) 0.058(9) 0.059(8) -0.001(7) 0.036(7) 0.014(7) C32 0.079(11) 0.047(8) 0.072(10) -0.003(7) 0.048(9) 0.009(7) C33 0.076(10) 0.044(8) 0.078(10) -0.020(7) 0.048(9) -0.023(7) C34 0.062(8) 0.070(10) 0.035(6) 0.003(7) 0.011(6) -0.015(8) C35 0.082(11) 0.053(8) 0.043(7) 0.012(7) 0.020(7) 0.008(8) C36 0.059(8) 0.031(6) 0.041(7) 0.001(5) 0.019(6) -0.007(6) _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 Ir C1 1.881(15) . ? Ir C2 2.152(14) . ? Ir C13 2.195(12) . ? Ir C15 2.231(12) . ? Ir C11 2.246(13) . ? Ir C14 2.249(12) . ? Ir C12 2.261(12) . ? Ir I 2.675(5) . ? O1 C1 1.068(16) . ? C2 F7 1.319(17) . ? C2 F6 1.375(16) . ? C2 C36 1.528(17) . ? F1 C31 1.337(15) . ? F2 C32 1.347(16) . ? F3 C33 1.332(15) . ? F4 C34 1.331(16) . ? F5 C35 1.325(15) . ? C11 C12 1.387(17) . ? C11 C15 1.442(18) . ? C11 C16 1.520(18) . ? C12 C17 1.470(18) . ? C12 C13 1.472(17) . ? C13 C14 1.466(17) . ? C13 C18 1.480(19) . ? C14 C15 1.442(18) . ? C14 C19 1.465(18) . ? C15 C20 1.481(19) . ? C31 C32 1.360(19) . ? C31 C36 1.387(17) . ? C32 C33 1.38(2) . ? C33 C34 1.345(19) . ? C34 C35 1.353(19) . ? C35 C36 1.389(18) . ? 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 C1 Ir C2 93.1(5) . . ? C1 Ir C13 107.4(5) . . ? C2 Ir C13 106.3(5) . . ? C1 Ir C15 155.8(5) . . ? C2 Ir C15 110.8(5) . . ? C13 Ir C15 63.5(5) . . ? C1 Ir C11 118.3(5) . . ? C2 Ir C11 148.3(5) . . ? C13 Ir C11 62.5(5) . . ? C15 Ir C11 37.6(5) . . ? C1 Ir C14 144.4(5) . . ? C2 Ir C14 90.0(5) . . ? C13 Ir C14 38.5(4) . . ? C15 Ir C14 37.5(5) . . ? C11 Ir C14 62.5(5) . . ? C1 Ir C12 96.2(5) . . ? C2 Ir C12 144.8(5) . . ? C13 Ir C12 38.6(4) . . ? C15 Ir C12 62.3(5) . . ? C11 Ir C12 35.9(4) . . ? C14 Ir C12 63.4(4) . . ? C1 Ir I 87.4(4) . . ? C2 Ir I 91.9(4) . . ? C13 Ir I 155.5(3) . . ? C15 Ir I 94.9(3) . . ? C11 Ir I 93.4(3) . . ? C14 Ir I 127.9(3) . . ? C12 Ir I 122.4(3) . . ? O1 C1 Ir 177.2(12) . . ? F7 C2 F6 105.6(12) . . ? F7 C2 C36 109.1(11) . . ? F6 C2 C36 108.4(11) . . ? F7 C2 Ir 109.8(9) . . ? F6 C2 Ir 106.9(9) . . ? C36 C2 Ir 116.4(10) . . ? C12 C11 C15 110.4(12) . . ? C12 C11 C16 126.6(13) . . ? C15 C11 C16 122.8(12) . . ? C12 C11 Ir 72.6(7) . . ? C15 C11 Ir 70.6(7) . . ? C16 C11 Ir 127.9(10) . . ? C11 C12 C17 128.1(12) . . ? C11 C12 C13 107.4(11) . . ? C17 C12 C13 124.6(12) . . ? C11 C12 Ir 71.5(7) . . ? C17 C12 Ir 126.4(9) . . ? C13 C12 Ir 68.3(6) . . ? C14 C13 C12 107.5(11) . . ? C14 C13 C18 126.2(12) . . ? C12 C13 C18 125.2(12) . . ? C14 C13 Ir 72.7(7) . . ? C12 C13 Ir 73.1(7) . . ? C18 C13 Ir 128.7(9) . . ? C15 C14 C19 128.6(12) . . ? C15 C14 C13 106.6(11) . . ? C19 C14 C13 124.3(13) . . ? C15 C14 Ir 70.6(7) . . ? C19 C14 Ir 131.8(10) . . ? C13 C14 Ir 68.8(6) . . ? C14 C15 C11 107.9(11) . . ? C14 C15 C20 124.5(13) . . ? C11 C15 C20 127.2(13) . . ? C14 C15 Ir 71.9(7) . . ? C11 C15 Ir 71.8(7) . . ? C20 C15 Ir 127.2(11) . . ? F1 C31 C32 115.8(12) . . ? F1 C31 C36 122.3(12) . . ? C32 C31 C36 121.8(13) . . ? F2 C32 C31 120.9(14) . . ? F2 C32 C33 118.5(14) . . ? C31 C32 C33 120.6(13) . . ? F3 C33 C34 120.1(15) . . ? F3 C33 C32 121.6(14) . . ? C34 C33 C32 118.3(12) . . ? F4 C34 C33 120.2(13) . . ? F4 C34 C35 118.3(14) . . ? C33 C34 C35 121.5(13) . . ? F5 C35 C34 118.3(13) . . ? F5 C35 C36 119.4(13) . . ? C34 C35 C36 122.0(13) . . ? C31 C36 C35 115.6(11) . . ? C31 C36 C2 120.2(12) . . ? C35 C36 C2 124.2(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.054 _refine_diff_density_min -3.787 _refine_diff_density_rms 0.237 #===END data_rph66r _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H15 F7 I Ir O' _chemical_formula_weight 651.36 _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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.999(9) _cell_length_b 14.477(5) _cell_length_c 13.553(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.32(4) _cell_angle_gamma 90.00 _cell_volume 1760(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.457 _exptl_crystal_density_method ? _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 9.404 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.467 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <7 _diffrn_reflns_number 3227 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0682 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 31.62 _reflns_number_total 2300 _reflns_number_observed 1592 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens/XSCANS' _computing_cell_refinement 'Siemens/XSCANS' _computing_data_reduction 'Siemens/XSCANS' _computing_structure_solution 'SHELXS-5.03 (Sheldrick, 1994)' _computing_structure_refinement 'SHELXL-5.03 (Sheldrick, 1994)' _computing_molecular_graphics 'XP-5.03' _computing_publication_material 'XCIF' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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^)+(0.0966P)^2^+41.9396P] 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 'idealized contributions' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2300 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_obs 0.0701 _refine_ls_wR_factor_all 0.1988 _refine_ls_wR_factor_obs 0.1692 _refine_ls_goodness_of_fit_all 1.039 _refine_ls_goodness_of_fit_obs 1.082 _refine_ls_restrained_S_all 1.039 _refine_ls_restrained_S_obs 1.082 _refine_ls_shift/esd_max 0.045 _refine_ls_shift/esd_mean 0.006 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 Ir Ir -0.39197(12) 0.71842(6) -0.08596(8) 0.0612(4) Uani 1 d . . I I -0.1800(2) 0.59360(12) -0.02843(15) 0.0777(6) Uani 1 d . . F1 F -0.3367(22) 0.9220(12) -0.0926(16) 0.122(7) Uani 1 d . . F2 F -0.2243(31) 0.7992(16) 0.1186(18) 0.154(10) Uani 1 d . . F3 F -0.2001(25) 0.9509(15) 0.0782(18) 0.143(8) Uani 1 d . . F4 F -0.4167(24) 0.8920(12) 0.0794(15) 0.116(7) Uani 1 d . . F5 F -0.0640(26) 0.9270(14) -0.0809(19) 0.146(9) Uani 1 d . . F6 F -0.0133(26) 0.8041(16) -0.0029(17) 0.132(8) Uani 1 d . . F7 F -0.0850(21) 0.7962(15) -0.1530(14) 0.113(6) Uani 1 d . . O1 O -0.5136(28) 0.6945(15) 0.1114(18) 0.112(8) Uani 1 d . . C1 C -0.4333(28) 0.7669(14) -0.2472(19) 0.060(7) Uani 1 d . . C2 C -0.5619(27) 0.7722(13) -0.1853(21) 0.064(7) Uani 1 d . . C3 C -0.6077(26) 0.6880(16) -0.1618(20) 0.064(7) Uani 1 d . . C4 C -0.5038(25) 0.6228(18) -0.1907(21) 0.070(8) Uani 1 d . . C5 C -0.3956(25) 0.6722(15) -0.2470(17) 0.051(6) Uani 1 d . . C6 C -0.3664(32) 0.8445(21) -0.3006(20) 0.084(8) Uani 1 d . . H6A H -0.4170(32) 0.9009(21) -0.2869(20) 0.126 Uiso 1 calc R . H6B H -0.3762(32) 0.8326(21) -0.3704(20) 0.126 Uiso 1 calc R . H6C H -0.2628(32) 0.8501(21) -0.2788(20) 0.126 Uiso 1 calc R . C7 C -0.6586(33) 0.8613(20) -0.1787(28) 0.108(12) Uani 1 d . . H7A H -0.6033(33) 0.9137(20) -0.1991(28) 0.162 Uiso 1 calc R . H7B H -0.6837(33) 0.8699(20) -0.1117(28) 0.162 Uiso 1 calc R . H7C H -0.7482(33) 0.8549(20) -0.2212(28) 0.162 Uiso 1 calc R . C8 C -0.7477(31) 0.6534(23) -0.1181(21) 0.089(9) Uani 1 d . . H8A H -0.7428(31) 0.5875(23) -0.1111(21) 0.134 Uiso 1 calc R . H8B H -0.8332(31) 0.6697(23) -0.1612(21) 0.134 Uiso 1 calc R . H8C H -0.7557(31) 0.6812(23) -0.0544(21) 0.134 Uiso 1 calc R . C9 C -0.5111(32) 0.5201(16) -0.1864(23) 0.085(9) Uani 1 d . . H9A H -0.4224(32) 0.4944(16) -0.2104(23) 0.127 Uiso 1 calc R . H9B H -0.5966(32) 0.4989(16) -0.2267(23) 0.127 Uiso 1 calc R . H9C H -0.5191(32) 0.5009(16) -0.1192(23) 0.127 Uiso 1 calc R . C10 C -0.2721(35) 0.6307(19) -0.2989(21) 0.090(10) Uani 1 d . . H10A H -0.2688(35) 0.5654(19) -0.2870(21) 0.135 Uiso 1 calc R . H10B H -0.1793(35) 0.6581(19) -0.2746(21) 0.135 Uiso 1 calc R . H10C H -0.2885(35) 0.6420(19) -0.3687(21) 0.135 Uiso 1 calc R . C11 C -0.4717(29) 0.7055(19) 0.0378(25) 0.081(9) Uani 1 d . . C12 C -0.2654(30) 0.8358(21) -0.0404(18) 0.072(8) Uani 1 d . . C13 C -0.2889(43) 0.8756(26) 0.0543(33) 0.117(13) Uani 1 d . . C14 C -0.1071(32) 0.8392(19) -0.0722(26) 0.076(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 Ir 0.0687(7) 0.0418(6) 0.0751(7) -0.0048(5) 0.0199(5) 0.0044(5) I 0.0828(13) 0.0611(11) 0.0897(13) 0.0041(10) 0.0108(10) 0.0162(10) F1 0.115(14) 0.072(11) 0.172(19) 0.043(12) -0.042(13) -0.033(11) F2 0.182(24) 0.115(17) 0.150(20) 0.026(15) -0.073(18) 0.004(16) F3 0.129(17) 0.113(16) 0.188(21) -0.075(16) 0.013(15) -0.030(14) F4 0.131(16) 0.075(11) 0.150(17) -0.021(11) 0.075(14) 0.012(11) F5 0.156(20) 0.079(13) 0.207(24) 0.033(14) 0.041(18) -0.021(13) F6 0.113(16) 0.151(20) 0.127(16) 0.002(15) -0.023(13) 0.011(14) F7 0.104(14) 0.142(17) 0.098(13) -0.013(13) 0.041(11) -0.019(12) O1 0.129(19) 0.097(16) 0.122(18) 0.017(13) 0.087(16) 0.001(14) C1 0.063(16) 0.029(13) 0.086(18) 0.006(12) -0.012(14) -0.010(12) C2 0.062(16) 0.016(11) 0.118(21) -0.001(12) 0.026(15) -0.010(11) C3 0.042(14) 0.058(16) 0.094(20) -0.013(14) 0.013(13) 0.014(12) C4 0.038(13) 0.062(16) 0.109(21) 0.034(15) -0.001(14) 0.002(12) C5 0.046(13) 0.048(13) 0.057(14) 0.000(11) -0.005(11) 0.001(11) C6 0.084(20) 0.092(21) 0.073(18) 0.007(17) -0.012(15) -0.023(18) C7 0.075(21) 0.074(21) 0.174(34) 0.007(21) 0.003(21) 0.045(17) C8 0.077(20) 0.112(25) 0.080(19) 0.023(19) 0.016(16) 0.007(19) C9 0.091(21) 0.040(14) 0.121(24) -0.013(15) -0.003(18) -0.022(14) C10 0.124(26) 0.067(18) 0.086(20) 0.002(16) 0.055(19) -0.021(18) C11 0.058(17) 0.076(18) 0.117(25) -0.015(17) 0.059(17) -0.033(14) C12 0.075(19) 0.092(20) 0.048(15) -0.027(15) -0.006(13) -0.009(16) C13 0.096(27) 0.091(25) 0.169(38) -0.038(27) 0.043(27) -0.032(23) C14 0.069(19) 0.057(17) 0.104(24) -0.003(17) 0.019(18) 0.004(15) _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 Ir C11 1.88(3) . ? Ir C12 2.11(3) . ? Ir C2 2.11(3) . ? Ir C4 2.17(3) . ? Ir C3 2.17(3) . ? Ir C5 2.28(2) . ? Ir C1 2.30(3) . ? Ir I 2.700(3) . ? F1 C12 1.55(3) . ? F2 C13 1.50(5) . ? F3 C13 1.38(4) . ? F4 C13 1.25(4) . ? F5 C14 1.34(3) . ? F6 C14 1.32(3) . ? F7 C14 1.29(3) . ? O1 C11 1.10(3) . ? C1 C5 1.41(3) . ? C1 C6 1.49(3) . ? C1 C2 1.48(3) . ? C2 C3 1.33(3) . ? C2 C7 1.56(3) . ? C3 C4 1.41(3) . ? C3 C8 1.52(3) . ? C4 C5 1.47(3) . ? C4 C9 1.49(3) . ? C5 C10 1.49(3) . ? C12 C13 1.44(4) . ? C12 C14 1.52(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 C11 Ir C12 93.0(10) . . ? C11 Ir C2 107.4(12) . . ? C12 Ir C2 103.8(9) . . ? C11 Ir C4 109.3(10) . . ? C12 Ir C4 156.3(10) . . ? C2 Ir C4 62.7(8) . . ? C11 Ir C3 90.8(11) . . ? C12 Ir C3 138.1(10) . . ? C2 Ir C3 36.3(9) . . ? C4 Ir C3 37.7(8) . . ? C11 Ir C5 147.6(10) . . ? C12 Ir C5 119.0(9) . . ? C2 Ir C5 62.6(9) . . ? C4 Ir C5 38.4(9) . . ? C3 Ir C5 62.6(9) . . ? C11 Ir C1 146.3(12) . . ? C12 Ir C1 94.4(9) . . ? C2 Ir C1 39.0(9) . . ? C4 Ir C1 62.6(8) . . ? C3 Ir C1 62.4(9) . . ? C5 Ir C1 35.9(8) . . ? C11 Ir I 89.1(10) . . ? C12 Ir I 95.7(8) . . ? C2 Ir I 153.4(6) . . ? C4 Ir I 92.6(6) . . ? C3 Ir I 126.0(6) . . ? C5 Ir I 92.2(6) . . ? C1 Ir I 122.6(6) . . ? C5 C1 C6 128.9(25) . . ? C5 C1 C2 104.3(19) . . ? C6 C1 C2 126.7(22) . . ? C5 C1 Ir 71.3(13) . . ? C6 C1 Ir 130.5(17) . . ? C2 C1 Ir 63.5(14) . . ? C3 C2 C1 110.9(19) . . ? C3 C2 C7 123.9(23) . . ? C1 C2 C7 122.5(21) . . ? C3 C2 Ir 74.5(16) . . ? C1 C2 Ir 77.5(14) . . ? C7 C2 Ir 130.5(21) . . ? C2 C3 C4 108.9(21) . . ? C2 C3 C8 132.5(23) . . ? C4 C3 C8 118.5(23) . . ? C2 C3 Ir 69.3(16) . . ? C4 C3 Ir 71.2(15) . . ? C8 C3 Ir 128.4(20) . . ? C3 C4 C5 107.4(21) . . ? C3 C4 C9 128.8(23) . . ? C5 C4 C9 122.7(24) . . ? C3 C4 Ir 71.1(16) . . ? C5 C4 Ir 74.8(14) . . ? C9 C4 Ir 129.0(20) . . ? C1 C5 C4 107.8(21) . . ? C1 C5 C10 125.4(22) . . ? C4 C5 C10 126.8(21) . . ? C1 C5 Ir 72.7(14) . . ? C4 C5 Ir 66.9(14) . . ? C10 C5 Ir 127.9(18) . . ? O1 C11 Ir 176.5(28) . . ? C13 C12 C14 116.3(26) . . ? C13 C12 F1 90.1(26) . . ? C14 C12 F1 102.0(23) . . ? C13 C12 Ir 118.2(22) . . ? C14 C12 Ir 116.1(19) . . ? F1 C12 Ir 108.6(14) . . ? F4 C13 F3 108.4(30) . . ? F4 C13 C12 121.4(35) . . ? F3 C13 C12 114.0(30) . . ? F4 C13 F2 107.9(32) . . ? F3 C13 F2 104.8(32) . . ? C12 C13 F2 98.4(28) . . ? F7 C14 F6 106.8(25) . . ? F7 C14 F5 108.7(27) . . ? F6 C14 F5 104.8(28) . . ? F7 C14 C12 115.6(26) . . ? F6 C14 C12 110.4(27) . . ? F5 C14 C12 109.9(25) . . ? _refine_diff_density_max 3.652 _refine_diff_density_min -1.890 _refine_diff_density_rms 0.248 #===END data_rph73r _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H24 F5 I Ir P' _chemical_formula_weight 649.41 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' '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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.7571(2) _cell_length_b 15.8571(3) _cell_length_c 16.8830(2) _cell_angle_alpha 90.00 _cell_angle_beta 118.0617(7) _cell_angle_gamma 90.00 _cell_volume 3958.75(15) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2432 _exptl_absorpt_coefficient_mu 8.424 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.440 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details DIFABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17159 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.33 _reflns_number_total 8123 _reflns_number_gt 6689 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 8123 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0959 _refine_ls_R_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.2313 _refine_ls_wR_factor_gt 0.2210 _refine_ls_goodness_of_fit_ref 1.637 _refine_ls_restrained_S_all 1.637 _refine_ls_shift/su_max 1.543 _refine_ls_shift/su_mean 0.061 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.76630(3) 0.03335(3) 0.75451(4) 0.0347(2) Uani 1 1 d . . . Ir1' Ir 0.74876(3) 0.26775(3) 1.22876(5) 0.0410(2) Uani 1 1 d . . . P1 P 0.8778(3) 0.0926(3) 0.7315(4) 0.0612(13) Uani 1 1 d . B . P1' P 0.8695(3) 0.3276(3) 1.2227(4) 0.0533(11) Uani 1 1 d . A . I1 I 0.8196(2) 0.13385(13) 0.90366(16) 0.1210(10) Uani 0.82 1 d P B . I1' I 0.78584(17) 0.36657(12) 1.37999(14) 0.0806(6) Uani 0.72 1 d P A . I1'A I 0.6401(6) 0.3507(7) 1.0604(8) 0.057(3) Uani 0.28 1 d P A 1 I1A I 0.6286(6) 0.1281(5) 0.6128(9) 0.070(4) Uani 0.18 1 d P B 1 C1 C 0.797(2) -0.0894(12) 0.836(2) 0.130(16) Uani 1 1 d . B . C1' C 0.7924(14) 0.1315(9) 1.2276(19) 0.080(7) Uani 1 1 d . A . C2 C 0.7143(15) -0.0657(10) 0.8116(17) 0.069(6) Uani 1 1 d . B . C2' C 0.7171(14) 0.1490(8) 1.1585(17) 0.068(7) Uani 1 1 d . A . C3 C 0.6674(10) -0.0715(9) 0.7194(15) 0.057(5) Uani 1 1 d . B . C3' C 0.6466(9) 0.1646(8) 1.1871(12) 0.044(4) Uani 1 1 d . A . C4 C 0.7172(16) -0.0926(9) 0.6827(14) 0.065(6) Uani 1 1 d . B . C4' C 0.6893(10) 0.1680(10) 1.2796(12) 0.047(4) Uani 1 1 d . A . C5 C 0.810(2) -0.0971(11) 0.760(3) 0.122(15) Uani 1 1 d . B . C5' C 0.7847(10) 0.1489(8) 1.3074(16) 0.064(6) Uani 1 1 d . A . C6 C 0.886(2) -0.0986(18) 0.929(3) 0.23(3) Uani 1 1 d . . . H6A H 0.8880 -0.1538 0.9531 0.346 Uiso 1 1 calc R B . H6B H 0.8862 -0.0568 0.9700 0.346 Uiso 1 1 calc R . . H6C H 0.9380 -0.0908 0.9197 0.346 Uiso 1 1 calc R . . C6' C 0.8781(15) 0.0998(13) 1.235(3) 0.161(18) Uani 1 1 d . . . H6'A H 0.8765 0.0393 1.2322 0.241 Uiso 1 1 calc R A . H6'B H 0.9273 0.1176 1.2911 0.241 Uiso 1 1 calc R . . H6'C H 0.8866 0.1218 1.1865 0.241 Uiso 1 1 calc R . . C7 C 0.674(3) -0.0561(14) 0.871(2) 0.18(2) Uani 1 1 d . . . H7A H 0.6602 -0.1107 0.8857 0.277 Uiso 1 1 calc R B . H7B H 0.6202 -0.0232 0.8420 0.277 Uiso 1 1 calc R . . H7C H 0.7167 -0.0282 0.9253 0.277 Uiso 1 1 calc R . . C7' C 0.6969(18) 0.1221(19) 1.0658(19) 0.118(10) Uani 1 1 d . . . H7'A H 0.6879 0.0621 1.0602 0.177 Uiso 1 1 calc R A . H7'B H 0.7466 0.1369 1.0553 0.177 Uiso 1 1 calc R . . H7'C H 0.6431 0.1499 1.0225 0.177 Uiso 1 1 calc R . . C8 C 0.5635(15) -0.0704(18) 0.670(3) 0.24(3) Uani 1 1 d . . . H8A H 0.5411 -0.1267 0.6667 0.363 Uiso 1 1 calc R B . H8B H 0.5429 -0.0492 0.6099 0.363 Uiso 1 1 calc R . . H8C H 0.5416 -0.0348 0.7012 0.363 Uiso 1 1 calc R . . C8' C 0.5437(12) 0.1649(12) 1.1205(16) 0.079(6) Uani 1 1 d . . . H8'A H 0.5196 0.1093 1.1169 0.119 Uiso 1 1 calc R A . H8'B H 0.5344 0.1819 1.0622 0.119 Uiso 1 1 calc R . . H8'C H 0.5136 0.2037 1.1412 0.119 Uiso 1 1 calc R . . C9 C 0.695(4) -0.1117(17) 0.595(3) 0.26(3) Uani 1 1 d . . . H9A H 0.6790 -0.1704 0.5840 0.395 Uiso 1 1 calc R B . H9B H 0.7453 -0.1002 0.5848 0.395 Uiso 1 1 calc R . . H9C H 0.6440 -0.0780 0.5553 0.395 Uiso 1 1 calc R . . C9' C 0.6419(19) 0.1792(13) 1.3330(18) 0.102(9) Uani 1 1 d . . . H9'A H 0.6234 0.1252 1.3444 0.153 Uiso 1 1 calc R A . H9'B H 0.5896 0.2141 1.3006 0.153 Uiso 1 1 calc R . . H9'C H 0.6816 0.2058 1.3890 0.153 Uiso 1 1 calc R . . C10' C 0.8487(16) 0.1365(12) 1.4035(17) 0.104(10) Uani 1 1 d . . . H10A H 0.8491 0.0781 1.4188 0.156 Uiso 1 1 calc R A . H10B H 0.8301 0.1703 1.4392 0.156 Uiso 1 1 calc R . . H10C H 0.9083 0.1531 1.4150 0.156 Uiso 1 1 calc R . . C10 C 0.894(3) -0.1302(16) 0.763(5) 0.33(5) Uani 1 1 d . . . H10D H 0.8947 -0.1906 0.7679 0.493 Uiso 1 1 calc R B . H10E H 0.9452 -0.1069 0.8137 0.493 Uiso 1 1 calc R . . H10F H 0.8955 -0.1146 0.7087 0.493 Uiso 1 1 calc R . . C11' C 0.8843(15) 0.2925(14) 1.1287(19) 0.103(10) Uani 1 1 d . . . H11A H 0.9360 0.3199 1.1301 0.155 Uiso 1 1 calc R A . H11B H 0.8313 0.3062 1.0737 0.155 Uiso 1 1 calc R . . H11C H 0.8934 0.2325 1.1323 0.155 Uiso 1 1 calc R . . C11 C 0.9909(15) 0.0713(17) 0.820(3) 0.152(15) Uani 1 1 d . . . H11D H 1.0342 0.0981 0.8064 0.229 Uiso 1 1 calc R B . H11E H 1.0012 0.0115 0.8252 0.229 Uiso 1 1 calc R . . H11F H 0.9971 0.0929 0.8759 0.229 Uiso 1 1 calc R . . C12' C 0.8715(13) 0.4457(11) 1.2125(17) 0.088(8) Uani 1 1 d . . . H12A H 0.9257 0.4623 1.2106 0.132 Uiso 1 1 calc R A . H12B H 0.8701 0.4715 1.2633 0.132 Uiso 1 1 calc R . . H12C H 0.8197 0.4636 1.1584 0.132 Uiso 1 1 calc R . . C12 C 0.8912(19) 0.0524(14) 0.635(2) 0.113(10) Uani 1 1 d . . . H12D H 0.9397 0.0820 0.6321 0.169 Uiso 1 1 calc R B . H12E H 0.8361 0.0611 0.5806 0.169 Uiso 1 1 calc R . . H12F H 0.9049 -0.0068 0.6432 0.169 Uiso 1 1 calc R . . C13' C 0.9787(14) 0.3031(14) 1.3162(16) 0.092(8) Uani 1 1 d . . . H13D H 1.0253 0.3307 1.3079 0.138 Uiso 1 1 calc R A . H13E H 0.9882 0.2433 1.3193 0.138 Uiso 1 1 calc R . . H13F H 0.9806 0.3225 1.3709 0.138 Uiso 1 1 calc R . . C13 C 0.8845(16) 0.2083(12) 0.7243(17) 0.092(8) Uani 1 1 d . . . H13A H 0.9349 0.2228 0.7148 0.138 Uiso 1 1 calc R B . H13B H 0.8923 0.2334 0.7792 0.138 Uiso 1 1 calc R . . H13C H 0.8297 0.2290 0.6752 0.138 Uiso 1 1 calc R . . C14' C 0.649(2) 0.3635(13) 1.135(4) 0.114(17) Uani 0.72 1 d P A . C14 C 0.668(2) 0.1236(13) 0.675(3) 0.079(10) Uani 0.82 1 d P B . C15' C 0.629(5) 0.362(4) 1.067(6) 0.07(2) Uiso 0.72 1 d P . . C15 C 0.6416(19) 0.1156(18) 0.589(2) 0.039(7) Uiso 0.82 1 d P . . F1 F 0.7112(13) 0.2094(8) 0.7144(17) 0.136(9) Uani 0.82 1 d P . . F1' F 0.5772(10) 0.3548(8) 1.1576(11) 0.070(4) Uani 0.72 1 d P . . F2 F 0.5986(8) 0.1167(8) 0.6818(15) 0.104(7) Uani 0.82 1 d P . . F2' F 0.6934(15) 0.4437(8) 1.1964(19) 0.133(10) Uani 0.72 1 d P . . F3 F 0.5781(15) 0.1885(13) 0.5409(17) 0.174(12) Uani 0.82 1 d P B . F3' F 0.5896(13) 0.2921(10) 1.0124(13) 0.095(6) Uani 0.72 1 d P A . F4 F 0.6010(19) 0.054(2) 0.541(2) 0.224(17) Uani 0.82 1 d P B . F4' F 0.6996(9) 0.3812(10) 1.0394(12) 0.081(5) Uani 0.72 1 d P A . F5 F 0.695(2) 0.1397(13) 0.5561(14) 0.153(10) Uani 0.82 1 d P B . F5' F 0.5657(9) 0.4251(10) 1.0143(11) 0.084(5) Uani 0.72 1 d P A . 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 Ir1 0.0328(3) 0.0291(3) 0.0513(4) -0.0012(2) 0.0273(3) 0.00009(17) Ir1' 0.0317(3) 0.0313(3) 0.0653(5) 0.0087(2) 0.0273(3) 0.00522(18) P1 0.053(2) 0.048(2) 0.097(4) 0.000(2) 0.047(3) -0.0108(18) P1' 0.0339(17) 0.046(2) 0.078(3) 0.022(2) 0.024(2) -0.0031(15) I1 0.229(3) 0.0795(12) 0.0853(17) -0.0396(11) 0.099(2) -0.0569(15) I1' 0.1125(16) 0.0683(11) 0.0556(13) -0.0164(9) 0.0350(12) 0.0046(10) I1'A 0.040(3) 0.059(4) 0.059(5) 0.029(3) 0.011(2) 0.009(2) I1A 0.046(4) 0.037(3) 0.067(7) -0.009(4) -0.022(5) 0.021(3) C1 0.15(3) 0.034(10) 0.09(2) 0.021(11) -0.041(19) -0.028(13) C1' 0.074(13) 0.029(8) 0.18(3) 0.014(10) 0.097(16) 0.001(7) C2 0.077(12) 0.037(8) 0.11(2) 0.022(10) 0.058(14) -0.010(8) C2' 0.083(13) 0.020(6) 0.16(2) -0.003(9) 0.103(16) -0.003(7) C3 0.036(7) 0.043(8) 0.090(16) 0.000(8) 0.028(9) -0.016(6) C3' 0.033(6) 0.038(7) 0.073(13) 0.006(7) 0.034(8) -0.008(5) C4 0.127(18) 0.022(7) 0.095(16) -0.019(8) 0.092(16) -0.026(9) C4' 0.034(7) 0.058(9) 0.047(11) 0.013(7) 0.018(8) -0.001(6) C5 0.14(2) 0.025(9) 0.29(5) 0.029(16) 0.17(3) 0.018(11) C5' 0.035(7) 0.025(7) 0.126(19) 0.018(8) 0.032(10) -0.005(5) C6 0.12(2) 0.11(2) 0.31(6) 0.14(3) -0.03(3) -0.036(18) C6' 0.096(17) 0.057(12) 0.40(5) 0.06(2) 0.18(3) 0.025(11) C7 0.41(6) 0.059(13) 0.24(4) -0.025(18) 0.28(5) -0.07(2) C7' 0.100(19) 0.18(3) 0.12(2) -0.02(2) 0.09(2) -0.014(19) C8 0.055(13) 0.16(3) 0.32(5) 0.16(3) -0.07(2) -0.068(16) C8' 0.048(9) 0.074(12) 0.098(18) 0.025(11) 0.019(11) -0.009(8) C9 0.61(10) 0.072(18) 0.20(4) -0.09(2) 0.26(6) -0.14(4) C9' 0.18(3) 0.065(12) 0.14(2) 0.030(13) 0.14(2) 0.034(14) C10' 0.089(15) 0.055(11) 0.089(19) 0.040(11) -0.024(14) -0.001(10) C10 0.24(4) 0.073(17) 0.88(14) 0.16(4) 0.44(7) 0.08(2) C11' 0.096(16) 0.096(15) 0.17(3) 0.074(16) 0.111(19) 0.050(13) C11 0.058(13) 0.13(2) 0.28(5) 0.05(2) 0.08(2) -0.018(13) C12' 0.053(10) 0.057(11) 0.12(2) 0.017(11) 0.016(12) -0.024(8) C12 0.14(2) 0.101(17) 0.18(3) 0.014(17) 0.15(2) 0.002(15) C13' 0.069(12) 0.095(15) 0.086(18) 0.035(13) 0.015(12) -0.026(11) C13 0.107(17) 0.056(11) 0.10(2) -0.007(11) 0.040(15) -0.043(11) C14' 0.09(2) 0.020(10) 0.31(6) -0.026(18) 0.16(3) -0.001(10) C14 0.088(19) 0.039(12) 0.15(3) 0.021(16) 0.09(2) 0.028(12) F1 0.176(16) 0.024(6) 0.31(3) 0.032(10) 0.199(19) 0.029(8) F1' 0.070(9) 0.064(8) 0.100(13) 0.024(8) 0.061(9) 0.024(7) F2 0.047(7) 0.056(8) 0.20(2) 0.056(10) 0.046(10) 0.027(6) F2' 0.148(17) 0.013(6) 0.30(3) 0.012(11) 0.16(2) 0.009(8) F3 0.135(18) 0.140(17) 0.16(2) 0.093(16) -0.005(16) 0.019(14) F3' 0.097(12) 0.062(9) 0.078(14) -0.010(9) 0.001(11) -0.009(9) F4 0.15(2) 0.25(3) 0.23(3) 0.17(3) 0.04(2) 0.08(2) F4' 0.042(7) 0.106(12) 0.085(13) 0.009(10) 0.022(8) -0.001(7) F5 0.22(3) 0.126(16) 0.068(14) 0.014(12) 0.033(16) 0.033(16) F5' 0.046(7) 0.093(11) 0.078(12) 0.049(9) 0.002(8) 0.017(7) _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 Ir1 C14 2.12(3) . ? Ir1 C5 2.178(18) . ? Ir1 C3 2.221(13) . ? Ir1 C2 2.224(15) . ? Ir1 C4 2.280(14) . ? Ir1 P1 2.283(4) . ? Ir1 C1 2.30(2) . ? Ir1 I1 2.7498(19) . ? Ir1 I1A 2.849(9) . ? Ir1' C2' 2.154(16) . ? Ir1' C14' 2.26(4) . ? Ir1' C5' 2.219(15) . ? Ir1' C3' 2.229(13) . ? Ir1' C4' 2.245(14) . ? Ir1' P1' 2.280(4) . ? Ir1' C1' 2.284(16) . ? Ir1' I1' 2.8051(19) . ? Ir1' I1'A 2.874(10) . ? P1 C11 1.81(3) . ? P1 C13 1.845(18) . ? P1 C12 1.86(2) . ? P1' C11' 1.81(3) . ? P1' C13' 1.81(2) . ? P1' C12' 1.882(17) . ? I1'A C14' 1.22(5) . ? I1'A F3' 1.26(2) . ? I1'A F4' 1.30(2) . ? I1'A F5' 1.624(16) . ? I1'A F1' 2.33(2) . ? I1'A F2' 2.51(3) . ? I1A C15 0.58(2) . ? I1A C14 0.94(4) . ? I1A F3 1.46(2) . ? I1A F2 1.48(3) . ? I1A F4 1.59(4) . ? I1A F5 1.78(3) . ? I1A F1 2.07(2) . ? C1 C2 1.30(4) . ? C1 C5 1.39(4) . ? C1 C6 1.59(4) . ? C1' C2' 1.28(3) . ? C1' C5' 1.44(3) . ? C1' C6' 1.47(2) . ? C2 C3 1.38(3) . ? C2 C7 1.45(3) . ? C2' C7' 1.50(3) . ? C2' C3' 1.492(19) . ? C3 C4 1.30(2) . ? C3 C8 1.54(3) . ? C3' C4' 1.38(2) . ? C3' C8' 1.55(2) . ? C4 C9 1.38(4) . ? C4 C5 1.48(4) . ? C4' C9' 1.47(2) . ? C4' C5' 1.47(2) . ? C5 C10 1.49(3) . ? C5' C10' 1.48(3) . ? C14' F1' 1.42(3) . ? C14' C15' 1.04(10) . ? C14' F2' 1.59(4) . ? C14 F2 1.23(3) . ? C14 C15 1.31(5) . ? C14 F1 1.54(3) . ? C15' F4' 1.49(8) . ? C15' F5' 1.43(6) . ? C15' F3' 1.40(8) . ? C15 F4 1.24(4) . ? C15 F5 1.31(4) . ? C15 F3 1.52(3) . ? 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 C14 Ir1 C5 144.3(16) . . ? C14 Ir1 C3 94.3(9) . . ? C5 Ir1 C3 59.5(8) . . ? C14 Ir1 C2 113.9(9) . . ? C5 Ir1 C2 60.1(8) . . ? C3 Ir1 C2 36.1(8) . . ? C14 Ir1 C4 106.0(12) . . ? C5 Ir1 C4 38.8(11) . . ? C3 Ir1 C4 33.4(6) . . ? C2 Ir1 C4 59.7(7) . . ? C14 Ir1 P1 93.9(6) . . ? C5 Ir1 P1 96.7(5) . . ? C3 Ir1 P1 146.1(5) . . ? C2 Ir1 P1 152.1(6) . . ? C4 Ir1 P1 112.9(4) . . ? C14 Ir1 C1 147.1(12) . . ? C5 Ir1 C1 36.2(11) . . ? C3 Ir1 C1 56.8(8) . . ? C2 Ir1 C1 33.3(11) . . ? C4 Ir1 C1 59.8(9) . . ? P1 Ir1 C1 118.8(11) . . ? C14 Ir1 I1 90.6(10) . . ? C5 Ir1 I1 123.5(12) . . ? C3 Ir1 I1 123.9(6) . . ? C2 Ir1 I1 92.1(6) . . ? C4 Ir1 I1 151.1(4) . . ? P1 Ir1 I1 88.73(15) . . ? C1 Ir1 I1 93.5(8) . . ? C14 Ir1 I1A 13.9(10) . . ? C5 Ir1 I1A 131.2(12) . . ? C3 Ir1 I1A 87.9(5) . . ? C2 Ir1 I1A 114.1(7) . . ? C4 Ir1 I1A 93.9(6) . . ? P1 Ir1 I1A 92.5(3) . . ? C1 Ir1 I1A 144.4(8) . . ? I1 Ir1 I1A 104.4(2) . . ? C2' Ir1' C14' 107.0(12) . . ? C2' Ir1' C5' 61.0(9) . . ? C14' Ir1' C5' 152.9(7) . . ? C2' Ir1' C3' 39.8(5) . . ? C14' Ir1' C3' 93.7(8) . . ? C5' Ir1' C3' 61.2(6) . . ? C2' Ir1' C4' 63.6(6) . . ? C14' Ir1' C4' 115.0(7) . . ? C5' Ir1' C4' 38.5(5) . . ? C3' Ir1' C4' 35.9(6) . . ? C2' Ir1' P1' 109.4(4) . . ? C14' Ir1' P1' 94.2(6) . . ? C5' Ir1' P1' 112.5(4) . . ? C3' Ir1' P1' 149.0(4) . . ? C4' Ir1' P1' 150.9(4) . . ? C2' Ir1' C1' 33.4(8) . . ? C14' Ir1' C1' 139.9(12) . . ? C5' Ir1' C1' 37.2(8) . . ? C3' Ir1' C1' 60.3(6) . . ? C4' Ir1' C1' 62.5(6) . . ? P1' Ir1' C1' 95.7(4) . . ? C2' Ir1' I1' 151.8(5) . . ? C14' Ir1' I1' 91.9(11) . . ? C5' Ir1' I1' 92.8(6) . . ? C3' Ir1' I1' 120.4(4) . . ? C4' Ir1' I1' 89.6(5) . . ? P1' Ir1' I1' 89.26(15) . . ? C1' Ir1' I1' 127.0(7) . . ? C2' Ir1' I1'A 88.7(7) . . ? C14' Ir1' I1'A 24.0(11) . . ? C5' Ir1' I1'A 148.0(6) . . ? C3' Ir1' I1'A 89.4(5) . . ? C4' Ir1' I1'A 120.8(4) . . ? P1' Ir1' I1'A 85.8(2) . . ? C1' Ir1' I1'A 118.7(8) . . ? I1' Ir1' I1'A 114.2(3) . . ? C11 P1 C13 99.7(11) . . ? C11 P1 C12 98.6(15) . . ? C13 P1 C12 104.4(11) . . ? C11 P1 Ir1 113.8(9) . . ? C13 P1 Ir1 120.0(8) . . ? C12 P1 Ir1 117.0(8) . . ? C11' P1' C13' 101.5(11) . . ? C11' P1' C12' 102.2(11) . . ? C13' P1' C12' 103.8(9) . . ? C11' P1' Ir1' 113.7(8) . . ? C13' P1' Ir1' 115.2(7) . . ? C12' P1' Ir1' 118.2(7) . . ? C14' I1'A F3' 120.1(16) . . ? C14' I1'A F4' 119.4(16) . . ? F3' I1'A F4' 118.0(18) . . ? C14' I1'A F5' 93.7(18) . . ? F3' I1'A F5' 95.5(11) . . ? F4' I1'A F5' 96.6(10) . . ? C14' I1'A F1' 30.4(14) . . ? F3' I1'A F1' 94.8(13) . . ? F4' I1'A F1' 147.3(12) . . ? F5' I1'A F1' 79.5(9) . . ? C14' I1'A F2' 30.5(12) . . ? F3' I1'A F2' 149.4(14) . . ? F4' I1'A F2' 92.5(10) . . ? F5' I1'A F2' 82.8(10) . . ? F1' I1'A F2' 54.8(7) . . ? C14' I1'A Ir1' 48.7(14) . . ? F3' I1'A Ir1' 102.6(9) . . ? F4' I1'A Ir1' 103.3(9) . . ? F5' I1'A Ir1' 142.4(10) . . ? F1' I1'A Ir1' 66.6(4) . . ? F2' I1'A Ir1' 65.0(5) . . ? C15 I1A C14 117(4) . . ? C15 I1A F3 84(4) . . ? C14 I1A F3 143.4(19) . . ? C15 I1A F2 153(4) . . ? C14 I1A F2 55.5(19) . . ? F3 I1A F2 117.1(15) . . ? C15 I1A F4 44(3) . . ? C14 I1A F4 126.4(17) . . ? F3 I1A F4 89.9(15) . . ? F2 I1A F4 115.4(15) . . ? C15 I1A F5 29(3) . . ? C14 I1A F5 108.5(19) . . ? F3 I1A F5 75.6(16) . . ? F2 I1A F5 164.1(11) . . ? F4 I1A F5 72.2(16) . . ? C15 I1A F1 118(4) . . ? C14 I1A F1 44.1(15) . . ? F3 I1A F1 100.4(11) . . ? F2 I1A F1 76.4(10) . . ? F4 I1A F1 158.7(14) . . ? F5 I1A F1 92.2(10) . . ? C15 I1A Ir1 89(3) . . ? C14 I1A Ir1 32.7(13) . . ? F3 I1A Ir1 165.1(13) . . ? F2 I1A Ir1 73.4(6) . . ? F4 I1A Ir1 94.8(8) . . ? F5 I1A Ir1 92.4(8) . . ? F1 I1A Ir1 70.8(5) . . ? C2 C1 C5 110(2) . . ? C2 C1 C6 135(4) . . ? C5 C1 C6 115(4) . . ? C2 C1 Ir1 70.3(11) . . ? C5 C1 Ir1 67.3(12) . . ? C6 C1 Ir1 120.6(14) . . ? C2' C1' C5' 109.1(15) . . ? C2' C1' C6' 131(3) . . ? C5' C1' C6' 120(3) . . ? C2' C1' Ir1' 67.7(10) . . ? C5' C1' Ir1' 68.9(9) . . ? C6' C1' Ir1' 128.8(12) . . ? C1 C2 C3 107(2) . . ? C1 C2 C7 126(3) . . ? C3 C2 C7 126(3) . . ? C1 C2 Ir1 76.3(14) . . ? C3 C2 Ir1 71.8(9) . . ? C7 C2 Ir1 128.9(14) . . ? C1' C2' C7' 122.0(18) . . ? C1' C2' C3' 109(2) . . ? C7' C2' C3' 124(2) . . ? C1' C2' Ir1' 78.8(13) . . ? C7' C2' Ir1' 134.4(15) . . ? C3' C2' Ir1' 72.8(8) . . ? C4 C3 C2 113.9(18) . . ? C4 C3 C8 124(3) . . ? C2 C3 C8 121(3) . . ? C4 C3 Ir1 75.8(9) . . ? C2 C3 Ir1 72.1(9) . . ? C8 C3 Ir1 130.5(13) . . ? C4' C3' C2' 107.8(15) . . ? C4' C3' C8' 128.8(15) . . ? C2' C3' C8' 123.0(19) . . ? C4' C3' Ir1' 72.7(8) . . ? C2' C3' Ir1' 67.4(8) . . ? C8' C3' Ir1' 130.7(10) . . ? C3 C4 C9 131(3) . . ? C3 C4 C5 103.3(19) . . ? C9 C4 C5 125(3) . . ? C3 C4 Ir1 70.8(9) . . ? C9 C4 Ir1 127.7(15) . . ? C5 C4 Ir1 66.9(10) . . ? C3' C4' C9' 124.0(17) . . ? C3' C4' C5' 105.1(15) . . ? C9' C4' C5' 131(2) . . ? C3' C4' Ir1' 71.4(8) . . ? C9' C4' Ir1' 128.0(13) . . ? C5' C4' Ir1' 69.8(8) . . ? C1 C5 C4 105(2) . . ? C1 C5 C10 124(4) . . ? C4 C5 C10 129(4) . . ? C1 C5 Ir1 76.5(13) . . ? C4 C5 Ir1 74.3(11) . . ? C10 C5 Ir1 129.0(15) . . ? C1' C5' C4' 107.6(17) . . ? C1' C5' C10' 131.7(19) . . ? C4' C5' C10' 120(2) . . ? C1' C5' Ir1' 73.8(10) . . ? C4' C5' Ir1' 71.7(8) . . ? C10' C5' Ir1' 128.5(12) . . ? I1'A C14' F1' 124(3) . . ? I1'A C14' C15' 13(4) . . ? F1' C14' C15' 115(5) . . ? I1'A C14' F2' 126(2) . . ? F1' C14' F2' 96(2) . . ? C15' C14' F2' 123(5) . . ? I1'A C14' Ir1' 107.3(12) . . ? F1' C14' Ir1' 101(2) . . ? C15' C14' Ir1' 120(4) . . ? F2' C14' Ir1' 97(2) . . ? I1A C14 F2 85(3) . . ? I1A C14 C15 23.2(16) . . ? F2 C14 C15 105(3) . . ? I1A C14 F1 111(2) . . ? F2 C14 F1 108.0(19) . . ? C15 C14 F1 114(2) . . ? I1A C14 Ir1 133(2) . . ? F2 C14 Ir1 111.6(19) . . ? C15 C14 Ir1 113.2(16) . . ? F1 C14 Ir1 105(2) . . ? F4' C15' F5' 97(5) . . ? F4' C15' F3' 99(5) . . ? F5' C15' F3' 99(5) . . ? F4' C15' C14' 118(6) . . ? F5' C15' C14' 116(6) . . ? F3' C15' C14' 124(7) . . ? I1A C15 F4 117(4) . . ? I1A C15 C14 40(3) . . ? F4 C15 C14 126(3) . . ? I1A C15 F5 139(4) . . ? F4 C15 F5 103(3) . . ? C14 C15 F5 120(3) . . ? I1A C15 F3 73(4) . . ? F4 C15 F3 102(2) . . ? C14 C15 F3 107(2) . . ? F5 C15 F3 90(2) . . ? C14 F1 I1A 25.1(14) . . ? C14' F1' I1'A 26(2) . . ? C14 F2 I1A 39(2) . . ? C14' F2' I1'A 23.1(16) . . ? I1A F3 C15 22.4(10) . . ? I1'A F3' C15' 12(3) . . ? C15 F4 I1A 19.0(15) . . ? C15' F4' I1'A 10(3) . . ? C15 F5 I1A 12.4(13) . . ? C15' F5' I1'A 9(4) . . ? _diffrn_measured_fraction_theta_max 0.823 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.823 _refine_diff_density_max 2.387 _refine_diff_density_min -3.321 _refine_diff_density_rms 0.280 #===END data_rph100 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 F7 I Ir P' _chemical_formula_weight 699.42 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' '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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(2)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 23.0016(3) _cell_length_b 23.0016(3) _cell_length_c 8.1951(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4335.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6407 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2624 _exptl_absorpt_coefficient_mu 7.712 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.782 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details DIFABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18533 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4151 _reflns_number_gt 3659 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 4151 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1571 _refine_ls_wR_factor_gt 0.1445 _refine_ls_goodness_of_fit_ref 1.288 _refine_ls_restrained_S_all 1.288 _refine_ls_shift/su_max 0.621 _refine_ls_shift/su_mean 0.100 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.809624(12) 0.520601(13) 0.06188(3) 0.03200(17) Uani 1 1 d . . . I1 I 0.89420(3) 0.56633(3) -0.13148(9) 0.0661(2) Uani 1 1 d . . . P1 P 0.88000(10) 0.46997(11) 0.2033(3) 0.0528(6) Uani 1 1 d . . . F1 F 0.7673(3) 0.4764(2) -0.2432(6) 0.0610(14) Uani 1 1 d . . . F2 F 0.8503(2) 0.4347(3) -0.1884(7) 0.0640(15) Uani 1 1 d . . . F3 F 0.7136(3) 0.4089(3) -0.0161(10) 0.0835(19) Uani 1 1 d . . . F4 F 0.7952(4) 0.3720(3) 0.0587(10) 0.101(3) Uani 1 1 d . . . F5 F 0.8140(5) 0.3272(5) -0.2298(19) 0.183(6) Uani 1 1 d . . . F6 F 0.7303(4) 0.3065(3) -0.1442(13) 0.126(3) Uani 1 1 d . . . F7 F 0.7401(7) 0.3696(5) -0.3305(13) 0.173(6) Uani 1 1 d . . . C1 C 0.7318(3) 0.5283(4) 0.2190(9) 0.0420(18) Uani 1 1 d . . . C2 C 0.7149(3) 0.5487(4) 0.0590(9) 0.0408(18) Uani 1 1 d . . . C3 C 0.7493(4) 0.5967(4) 0.0204(9) 0.0411(17) Uani 1 1 d . . . C4 C 0.7870(4) 0.6112(4) 0.1596(10) 0.0476(19) Uani 1 1 d . . . C5 C 0.7744(4) 0.5698(4) 0.2814(9) 0.049(2) Uani 1 1 d . . . C6 C 0.6994(5) 0.4839(5) 0.3203(15) 0.078(4) Uani 1 1 d . . . H6A H 0.6674 0.5024 0.3748 0.117 Uiso 1 1 calc R . . H6B H 0.7253 0.4675 0.3998 0.117 Uiso 1 1 calc R . . H6C H 0.6850 0.4537 0.2504 0.117 Uiso 1 1 calc R . . C7 C 0.6635(4) 0.5258(5) -0.0342(14) 0.067(3) Uani 1 1 d . . . H7A H 0.6295 0.5481 -0.0067 0.100 Uiso 1 1 calc R . . H7B H 0.6571 0.4858 -0.0063 0.100 Uiso 1 1 calc R . . H7C H 0.6708 0.5290 -0.1492 0.100 Uiso 1 1 calc R . . C8 C 0.7434(5) 0.6342(5) -0.1291(12) 0.070(3) Uani 1 1 d . . . H8A H 0.7140 0.6631 -0.1109 0.106 Uiso 1 1 calc R . . H8B H 0.7327 0.6105 -0.2207 0.106 Uiso 1 1 calc R . . H8C H 0.7799 0.6530 -0.1510 0.106 Uiso 1 1 calc R . . C9 C 0.8258(5) 0.6613(5) 0.1713(15) 0.075(3) Uani 1 1 d . . . H9A H 0.8050 0.6938 0.2155 0.113 Uiso 1 1 calc R . . H9B H 0.8401 0.6710 0.0646 0.113 Uiso 1 1 calc R . . H9C H 0.8580 0.6519 0.2413 0.113 Uiso 1 1 calc R . . C10 C 0.7954(6) 0.5718(6) 0.4587(11) 0.083(4) Uani 1 1 d . . . H10A H 0.7699 0.5960 0.5216 0.124 Uiso 1 1 calc R . . H10B H 0.8341 0.5873 0.4623 0.124 Uiso 1 1 calc R . . H10C H 0.7954 0.5332 0.5032 0.124 Uiso 1 1 calc R . . C11 C 0.7998(4) 0.4541(4) -0.1113(9) 0.0437(18) Uani 1 1 d . . . C12 C 0.7682(4) 0.3977(4) -0.0656(11) 0.053(2) Uani 1 1 d . . . C13 C 0.7634(6) 0.3500(6) -0.205(2) 0.092(4) Uani 1 1 d . . . C14 C 0.8550(6) 0.4267(6) 0.3749(12) 0.077(3) Uani 1 1 d . . . H14A H 0.8876 0.4076 0.4247 0.115 Uiso 1 1 calc R . . H14B H 0.8277 0.3981 0.3371 0.115 Uiso 1 1 calc R . . H14C H 0.8365 0.4515 0.4534 0.115 Uiso 1 1 calc R . . C15 C 0.9319(5) 0.5199(6) 0.2985(18) 0.093(4) Uani 1 1 d . . . H15A H 0.9608 0.4981 0.3565 0.140 Uiso 1 1 calc R . . H15B H 0.9118 0.5450 0.3731 0.140 Uiso 1 1 calc R . . H15C H 0.9504 0.5429 0.2156 0.140 Uiso 1 1 calc R . . C16 C 0.9282(6) 0.4203(6) 0.0926(16) 0.085(4) Uani 1 1 d . . . H16A H 0.9549 0.4027 0.1677 0.128 Uiso 1 1 calc R . . H16B H 0.9494 0.4416 0.0114 0.128 Uiso 1 1 calc R . . H16C H 0.9054 0.3906 0.0407 0.128 Uiso 1 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 Ir1 0.0290(2) 0.0377(2) 0.0293(2) 0.00062(10) 0.00084(9) -0.00054(10) I1 0.0498(4) 0.0759(5) 0.0725(5) 0.0112(3) 0.0211(3) -0.0132(3) P1 0.0467(13) 0.0645(15) 0.0472(12) -0.0022(10) -0.0116(10) 0.0188(11) F1 0.080(4) 0.063(3) 0.040(2) -0.010(2) -0.014(2) 0.004(3) F2 0.059(3) 0.071(4) 0.062(3) -0.025(3) 0.016(3) 0.006(3) F3 0.068(4) 0.057(4) 0.126(5) -0.007(4) 0.037(4) -0.011(3) F4 0.120(7) 0.051(4) 0.132(7) 0.037(4) -0.040(5) -0.017(4) F5 0.146(9) 0.117(8) 0.287(17) -0.134(10) 0.056(10) -0.003(7) F6 0.120(7) 0.059(5) 0.199(9) -0.039(5) -0.003(7) -0.019(5) F7 0.290(16) 0.102(7) 0.127(8) -0.024(6) -0.074(10) -0.074(9) C1 0.034(4) 0.048(5) 0.044(4) 0.007(3) 0.014(3) 0.012(3) C2 0.031(4) 0.045(5) 0.047(4) -0.007(3) -0.001(3) 0.012(3) C3 0.043(4) 0.045(4) 0.036(4) 0.007(3) 0.002(3) 0.006(3) C4 0.056(5) 0.039(4) 0.048(4) -0.008(3) -0.003(4) 0.004(4) C5 0.042(5) 0.069(6) 0.037(4) -0.007(4) 0.001(3) 0.005(4) C6 0.087(8) 0.060(6) 0.087(8) 0.002(5) 0.053(7) -0.004(5) C7 0.041(5) 0.068(7) 0.091(7) -0.019(5) -0.020(5) 0.009(5) C8 0.088(8) 0.073(7) 0.050(5) 0.028(5) 0.002(5) 0.015(6) C9 0.079(8) 0.061(7) 0.086(7) -0.020(6) 0.014(6) -0.025(6) C10 0.124(11) 0.089(9) 0.035(5) -0.020(5) 0.002(5) 0.026(8) C11 0.044(5) 0.052(5) 0.034(4) -0.007(3) -0.001(3) 0.007(4) C12 0.046(5) 0.052(6) 0.062(6) -0.008(4) -0.011(4) 0.007(4) C13 0.082(9) 0.056(7) 0.137(13) -0.041(8) -0.006(9) 0.007(6) C14 0.093(8) 0.089(8) 0.048(5) 0.025(5) -0.008(5) 0.021(7) C15 0.050(6) 0.112(10) 0.118(10) -0.024(8) -0.048(7) 0.002(6) C16 0.078(8) 0.084(9) 0.094(8) -0.019(7) -0.022(6) 0.037(7) _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 Ir1 C11 2.098(8) . ? Ir1 C1 2.212(7) . ? Ir1 C3 2.259(8) . ? Ir1 C5 2.275(8) . ? Ir1 C2 2.274(8) . ? Ir1 C4 2.292(8) . ? Ir1 P1 2.307(2) . ? Ir1 I1 2.7206(6) . ? P1 C14 1.816(11) . ? P1 C15 1.832(11) . ? P1 C16 1.831(12) . ? F1 C11 1.411(9) . ? F2 C11 1.395(9) . ? F3 C12 1.345(11) . ? F4 C12 1.330(11) . ? F5 C13 1.292(16) . ? F6 C13 1.354(17) . ? F7 C13 1.245(18) . ? C1 C5 1.458(12) . ? C1 C2 1.446(11) . ? C1 C6 1.513(12) . ? C2 C3 1.395(12) . ? C2 C7 1.503(12) . ? C3 C4 1.472(11) . ? C3 C8 1.505(11) . ? C4 C5 1.409(12) . ? C4 C9 1.461(13) . ? C5 C10 1.532(12) . ? C11 C12 1.535(13) . ? C12 C13 1.587(15) . ? 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 C11 Ir1 C1 111.5(3) . . ? C11 Ir1 C3 113.4(3) . . ? C1 Ir1 C3 61.8(3) . . ? C11 Ir1 C5 149.2(3) . . ? C1 Ir1 C5 37.9(3) . . ? C3 Ir1 C5 61.0(3) . . ? C11 Ir1 C2 95.6(3) . . ? C1 Ir1 C2 37.6(3) . . ? C3 Ir1 C2 35.8(3) . . ? C5 Ir1 C2 61.6(3) . . ? C11 Ir1 C4 151.0(3) . . ? C1 Ir1 C4 62.6(3) . . ? C3 Ir1 C4 37.7(3) . . ? C5 Ir1 C4 35.9(3) . . ? C2 Ir1 C4 61.8(3) . . ? C11 Ir1 P1 92.7(2) . . ? C1 Ir1 P1 108.4(2) . . ? C3 Ir1 P1 153.9(2) . . ? C5 Ir1 P1 96.0(2) . . ? C2 Ir1 P1 145.2(2) . . ? C4 Ir1 P1 116.3(2) . . ? C11 Ir1 I1 88.0(2) . . ? C1 Ir1 I1 152.4(2) . . ? C3 Ir1 I1 93.0(2) . . ? C5 Ir1 I1 121.5(2) . . ? C2 Ir1 I1 124.7(2) . . ? C4 Ir1 I1 90.8(2) . . ? P1 Ir1 I1 89.20(7) . . ? C14 P1 C15 102.8(6) . . ? C14 P1 C16 103.5(6) . . ? C15 P1 C16 102.0(6) . . ? C14 P1 Ir1 116.3(4) . . ? C15 P1 Ir1 110.8(4) . . ? C16 P1 Ir1 119.4(4) . . ? C5 C1 C2 106.7(7) . . ? C5 C1 C6 125.5(8) . . ? C2 C1 C6 125.6(9) . . ? C5 C1 Ir1 73.4(4) . . ? C2 C1 Ir1 73.5(4) . . ? C6 C1 Ir1 131.6(6) . . ? C3 C2 C1 108.0(7) . . ? C3 C2 C7 127.4(8) . . ? C1 C2 C7 124.1(9) . . ? C3 C2 Ir1 71.5(5) . . ? C1 C2 Ir1 68.9(4) . . ? C7 C2 Ir1 131.3(6) . . ? C2 C3 C4 109.7(7) . . ? C2 C3 C8 126.1(8) . . ? C4 C3 C8 123.6(8) . . ? C2 C3 Ir1 72.6(5) . . ? C4 C3 Ir1 72.3(4) . . ? C8 C3 Ir1 128.5(6) . . ? C5 C4 C3 105.9(7) . . ? C5 C4 C9 127.8(9) . . ? C3 C4 C9 126.1(9) . . ? C5 C4 Ir1 71.4(5) . . ? C3 C4 Ir1 69.9(4) . . ? C9 C4 Ir1 126.9(7) . . ? C4 C5 C1 109.4(7) . . ? C4 C5 C10 125.9(9) . . ? C1 C5 C10 124.3(9) . . ? C4 C5 Ir1 72.7(5) . . ? C1 C5 Ir1 68.7(4) . . ? C10 C5 Ir1 130.7(7) . . ? F2 C11 F1 102.2(6) . . ? F2 C11 C12 103.4(7) . . ? F1 C11 C12 104.1(7) . . ? F2 C11 Ir1 116.8(6) . . ? F1 C11 Ir1 108.1(5) . . ? C12 C11 Ir1 120.2(5) . . ? F4 C12 F3 106.8(9) . . ? F4 C12 C11 109.9(8) . . ? F3 C12 C11 110.7(8) . . ? F4 C12 C13 106.1(9) . . ? F3 C12 C13 106.5(9) . . ? C11 C12 C13 116.3(9) . . ? F7 C13 F5 113.9(17) . . ? F7 C13 F6 109.2(13) . . ? F5 C13 F6 105.4(12) . . ? F7 C13 C12 112.0(11) . . ? F5 C13 C12 109.4(11) . . ? F6 C13 C12 106.6(12) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 1.250 _refine_diff_density_min -1.574 _refine_diff_density_rms 0.126 #===END data_rph70o _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H24 F7 I Ir P' _chemical_formula_weight 699.42 _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' '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' 'Ir' 'Ir' -1.4442 7.9887 '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 P2(1)2(1)2(1) 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' _cell_length_a 8.68413(4) _cell_length_b 13.6408(2) _cell_length_c 18.0396(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2136.94(3) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.174 _exptl_crystal_density_method ? _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 7.824 _exptl_absorpt_correction_type 'Empirical from DIFABS' _exptl_absorpt_correction_T_min 0.400 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7477 _diffrn_reflns_av_R_equivalents 0.0820 _diffrn_reflns_av_sigmaI/netI 0.1253 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.13 _reflns_number_total 4394 _reflns_number_observed 3660 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 0 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^)+(0.0400P)^2^+0.0000P] 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 ? _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 0.06(2) _refine_ls_number_reflns 4394 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_obs 0.0651 _refine_ls_wR_factor_all 0.1517 _refine_ls_wR_factor_obs 0.1490 _refine_ls_goodness_of_fit_all 1.068 _refine_ls_goodness_of_fit_obs 1.153 _refine_ls_restrained_S_all 1.068 _refine_ls_restrained_S_obs 1.153 _refine_ls_shift/esd_max 0.000 _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 Ir1 Ir -0.10202(6) 0.48907(4) -0.38335(3) 0.0252(2) Uani 1 d . . I1 I -0.3453(2) 0.44291(10) -0.47413(7) 0.0517(4) Uani 1 d . . P1 P 0.0249(6) 0.5439(4) -0.4896(2) 0.0422(11) Uani 1 d . . F1 F -0.2715(14) 0.6714(8) -0.4319(5) 0.053(3) Uani 1 d . . F2 F -0.4190(15) 0.5407(10) -0.3059(8) 0.081(4) Uani 1 d . . F3 F -0.3127(22) 0.6520(12) -0.2424(6) 0.103(6) Uani 1 d . . F4 F -0.4634(19) 0.6901(12) -0.3308(8) 0.097(6) Uani 1 d . . F5 F -0.0267(20) 0.6893(8) -0.2744(7) 0.087(5) Uani 1 d . . F6 F 0.0044(17) 0.7331(9) -0.3873(8) 0.081(4) Uani 1 d . . F7 F -0.1785(22) 0.7984(9) -0.3233(7) 0.094(5) Uani 1 d . . C1 C -0.0607(21) 0.3295(10) -0.3591(8) 0.030(4) Uani 1 d . . C2 C -0.1570(22) 0.3691(12) -0.3013(10) 0.041(4) Uani 1 d . . C3 C -0.0799(22) 0.4395(11) -0.2619(7) 0.035(4) Uani 1 d . . C4 C 0.0755(17) 0.4558(11) -0.2983(9) 0.035(4) Uani 1 d . . C5 C 0.0803(21) 0.3750(12) -0.3570(8) 0.036(4) Uani 1 d . . C6 C -0.0998(30) 0.2429(12) -0.4092(9) 0.056(5) Uani 1 d . . H6A H -0.2069(30) 0.2232(12) -0.4009(9) 0.083 Uiso 1 calc R . H6B H -0.0313(30) 0.1878(12) -0.3977(9) 0.083 Uiso 1 calc R . H6C H -0.0861(30) 0.2620(12) -0.4612(9) 0.083 Uiso 1 calc R . C7 C -0.3143(22) 0.3242(13) -0.2813(11) 0.047(5) Uani 1 d . . H7A H -0.3431(22) 0.2756(13) -0.3188(11) 0.071 Uiso 1 calc R . H7B H -0.3924(22) 0.3761(13) -0.2797(11) 0.071 Uiso 1 calc R . H7C H -0.3077(22) 0.2925(13) -0.2327(11) 0.071 Uiso 1 calc R . C8 C -0.1202(24) 0.4814(14) -0.1870(8) 0.055(5) Uani 1 d . . H8A H -0.0435(24) 0.5308(14) -0.1730(8) 0.082 Uiso 1 calc R . H8B H -0.1212(24) 0.4288(14) -0.1501(8) 0.082 Uiso 1 calc R . H8C H -0.2222(24) 0.5120(14) -0.1893(8) 0.082 Uiso 1 calc R . C9 C 0.2082(25) 0.5078(17) -0.2669(12) 0.073(7) Uani 1 d . . H9A H 0.2932(25) 0.5070(17) -0.3026(12) 0.109 Uiso 1 calc R . H9B H 0.2407(25) 0.4752(17) -0.2211(12) 0.109 Uiso 1 calc R . H9C H 0.1794(25) 0.5757(17) -0.2561(12) 0.109 Uiso 1 calc R . C10 C 0.2283(23) 0.3434(18) -0.3955(11) 0.066(6) Uani 1 d . . H10A H 0.3106(23) 0.3901(18) -0.3839(11) 0.099 Uiso 1 calc R . H10B H 0.2117(23) 0.3418(18) -0.4493(11) 0.099 Uiso 1 calc R . H10C H 0.2578(23) 0.2779(18) -0.3782(11) 0.099 Uiso 1 calc R . C11 C -0.2125(24) 0.6305(12) -0.3625(9) 0.044(5) Uani 1 d . . C12 C -0.3602(28) 0.6262(17) -0.3135(12) 0.063(6) Uani 1 d . . C13 C -0.0913(35) 0.7090(13) -0.3381(9) 0.060(6) Uani 1 d . . C14 C -0.0630(26) 0.6388(14) -0.5475(9) 0.057(6) Uani 1 d . . H14A H -0.1700(26) 0.6210(14) -0.5584(9) 0.086 Uiso 1 calc R . H14B H -0.0054(26) 0.6446(14) -0.5940(9) 0.086 Uiso 1 calc R . H14C H -0.0606(26) 0.7016(14) -0.5212(9) 0.086 Uiso 1 calc R . C15 C 0.0569(29) 0.4433(16) -0.5546(9) 0.065(6) Uani 1 d . . H15A H -0.0415(29) 0.4113(16) -0.5657(9) 0.098 Uiso 1 calc R . H15B H 0.1276(29) 0.3955(16) -0.5325(9) 0.098 Uiso 1 calc R . H15C H 0.1017(29) 0.4690(16) -0.6005(9) 0.098 Uiso 1 calc R . C16 C 0.2157(26) 0.5912(21) -0.4772(11) 0.075(8) Uani 1 d . . H16A H 0.2128(26) 0.6467(21) -0.4427(11) 0.113 Uiso 1 calc R . H16B H 0.2564(26) 0.6132(21) -0.5251(11) 0.113 Uiso 1 calc R . H16C H 0.2823(26) 0.5397(21) -0.4570(11) 0.113 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 Ir1 0.0301(3) 0.0302(3) 0.0152(2) -0.0006(2) 0.0011(2) 0.0005(3) I1 0.0544(8) 0.0594(8) 0.0414(6) 0.0014(6) -0.0181(6) -0.0091(6) P1 0.050(3) 0.052(3) 0.024(2) 0.013(2) 0.010(2) 0.001(2) F1 0.066(8) 0.056(7) 0.037(5) 0.004(5) -0.009(5) 0.019(6) F2 0.062(9) 0.088(10) 0.094(10) -0.001(8) 0.037(7) 0.004(7) F3 0.142(15) 0.128(13) 0.037(6) -0.020(8) 0.011(8) 0.018(12) F4 0.101(12) 0.111(12) 0.080(10) 0.033(9) 0.044(9) 0.062(10) F5 0.145(14) 0.046(6) 0.069(8) -0.024(6) -0.059(9) 0.005(8) F6 0.096(11) 0.058(7) 0.087(10) -0.028(8) -0.009(9) -0.028(7) F7 0.157(15) 0.041(6) 0.084(9) -0.021(6) -0.030(10) 0.011(8) C1 0.051(11) 0.023(7) 0.016(6) -0.001(5) -0.003(6) -0.004(7) C2 0.047(11) 0.034(8) 0.043(9) 0.015(8) 0.011(8) 0.003(8) C3 0.063(12) 0.027(7) 0.014(6) 0.010(6) -0.002(7) 0.003(8) C4 0.020(9) 0.037(8) 0.048(9) -0.009(7) 0.000(6) -0.010(6) C5 0.047(11) 0.041(8) 0.020(6) 0.008(6) -0.016(7) 0.020(8) C6 0.090(16) 0.043(9) 0.034(8) -0.017(8) -0.013(11) 0.020(12) C7 0.040(11) 0.048(11) 0.054(11) 0.015(9) 0.004(9) 0.011(9) C8 0.072(13) 0.062(11) 0.030(8) 0.004(8) 0.005(8) 0.002(12) C9 0.072(15) 0.066(14) 0.080(13) 0.008(13) -0.034(12) -0.039(13) C10 0.044(12) 0.096(17) 0.058(12) 0.029(13) 0.009(10) 0.023(12) C11 0.066(13) 0.028(8) 0.037(9) -0.006(7) 0.021(8) 0.011(8) C12 0.067(16) 0.063(13) 0.059(13) 0.023(11) 0.030(12) 0.021(12) C13 0.118(20) 0.039(9) 0.022(8) -0.009(7) 0.018(12) -0.022(13) C14 0.084(17) 0.059(11) 0.029(9) 0.026(9) 0.008(9) 0.005(11) C15 0.095(18) 0.071(13) 0.031(9) 0.002(9) 0.009(10) 0.013(13) C16 0.061(15) 0.111(21) 0.054(12) 0.038(14) 0.031(11) 0.005(14) _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 Ir1 C11 2.19(2) . ? Ir1 C4 2.22(2) . ? Ir1 C1 2.249(14) . ? Ir1 C2 2.26(2) . ? Ir1 C5 2.271(15) . ? Ir1 C3 2.300(13) . ? Ir1 P1 2.333(4) . ? Ir1 I1 2.7466(13) . ? P1 C16 1.79(2) . ? P1 C15 1.83(2) . ? P1 C14 1.83(2) . ? F1 C11 1.46(2) . ? F2 C12 1.28(3) . ? F3 C12 1.39(3) . ? F4 C12 1.29(2) . ? F5 C13 1.31(2) . ? F6 C13 1.26(2) . ? F7 C13 1.46(3) . ? C1 C5 1.37(2) . ? C1 C2 1.44(2) . ? C1 C6 1.53(2) . ? C2 C3 1.37(2) . ? C2 C7 1.54(3) . ? C3 C8 1.51(2) . ? C3 C4 1.52(2) . ? C4 C9 1.47(2) . ? C4 C5 1.53(2) . ? C5 C10 1.52(2) . ? C11 C12 1.56(3) . ? C11 C13 1.56(3) . ? 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 C11 Ir1 C4 111.4(6) . . ? C11 Ir1 C1 152.9(6) . . ? C4 Ir1 C1 63.8(6) . . ? C11 Ir1 C2 115.7(6) . . ? C4 Ir1 C2 63.0(6) . . ? C1 Ir1 C2 37.3(6) . . ? C11 Ir1 C5 151.0(7) . . ? C4 Ir1 C5 39.8(5) . . ? C1 Ir1 C5 35.4(6) . . ? C2 Ir1 C5 60.9(6) . . ? C11 Ir1 C3 97.6(6) . . ? C4 Ir1 C3 39.1(6) . . ? C1 Ir1 C3 61.1(5) . . ? C2 Ir1 C3 35.0(6) . . ? C5 Ir1 C3 62.7(6) . . ? C11 Ir1 P1 93.8(4) . . ? C4 Ir1 P1 107.8(4) . . ? C1 Ir1 P1 113.2(4) . . ? C2 Ir1 P1 150.5(5) . . ? C5 Ir1 P1 93.6(4) . . ? C3 Ir1 P1 146.8(5) . . ? C11 Ir1 I1 88.1(5) . . ? C4 Ir1 I1 154.0(4) . . ? C1 Ir1 I1 90.9(4) . . ? C2 Ir1 I1 93.5(5) . . ? C5 Ir1 I1 120.3(4) . . ? C3 Ir1 I1 124.4(5) . . ? P1 Ir1 I1 86.97(13) . . ? C16 P1 C15 102.1(12) . . ? C16 P1 C14 101.6(11) . . ? C15 P1 C14 103.2(9) . . ? C16 P1 Ir1 116.7(7) . . ? C15 P1 Ir1 111.0(7) . . ? C14 P1 Ir1 119.9(7) . . ? C5 C1 C2 109.2(14) . . ? C5 C1 C6 124.3(17) . . ? C2 C1 C6 126.1(17) . . ? C5 C1 Ir1 73.2(8) . . ? C2 C1 Ir1 71.7(8) . . ? C6 C1 Ir1 126.8(11) . . ? C3 C2 C1 110.8(16) . . ? C3 C2 C7 126.2(17) . . ? C1 C2 C7 122.4(16) . . ? C3 C2 Ir1 74.2(9) . . ? C1 C2 Ir1 71.0(8) . . ? C7 C2 Ir1 129.0(12) . . ? C2 C3 C8 128.1(17) . . ? C2 C3 C4 108.3(14) . . ? C8 C3 C4 122.6(15) . . ? C2 C3 Ir1 70.8(8) . . ? C8 C3 Ir1 136.3(11) . . ? C4 C3 Ir1 67.7(8) . . ? C9 C4 C3 127.1(16) . . ? C9 C4 C5 126.4(16) . . ? C3 C4 C5 102.6(12) . . ? C9 C4 Ir1 135.5(14) . . ? C3 C4 Ir1 73.2(8) . . ? C5 C4 Ir1 71.8(8) . . ? C1 C5 C10 127.7(16) . . ? C1 C5 C4 108.7(14) . . ? C10 C5 C4 122.9(16) . . ? C1 C5 Ir1 71.4(9) . . ? C10 C5 Ir1 133.4(12) . . ? C4 C5 Ir1 68.4(8) . . ? F1 C11 C12 102.2(16) . . ? F1 C11 C13 102.5(13) . . ? C12 C11 C13 114.8(16) . . ? F1 C11 Ir1 110.0(9) . . ? C12 C11 Ir1 115.2(13) . . ? C13 C11 Ir1 110.9(14) . . ? F2 C12 F4 111.3(22) . . ? F2 C12 F3 104.4(17) . . ? F4 C12 F3 105.0(19) . . ? F2 C12 C11 115.0(18) . . ? F4 C12 C11 114.2(16) . . ? F3 C12 C11 105.6(19) . . ? F6 C13 F5 113.0(25) . . ? F6 C13 F7 104.6(15) . . ? F5 C13 F7 103.5(13) . . ? F6 C13 C11 115.1(14) . . ? F5 C13 C11 113.3(15) . . ? F7 C13 C11 105.9(21) . . ? _refine_diff_density_max 3.029 _refine_diff_density_min -3.558 _refine_diff_density_rms 0.308 #===END