# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_gs50a _database_code_depnum_ccdc_archive 'CCDC 890056' #TrackingRef 'GS50A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C34 H22 F4 Ir N6), 4(F6 P), 3(C H2 Cl2)' _chemical_formula_sum 'C139 H94 Cl6 F40 Ir4 N24 P4' _chemical_formula_weight 3965.84 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 '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 _symmetry_space_group_name_Hall -P2yn 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 16.662(5) _cell_length_b 10.561(3) _cell_length_c 19.725(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.00(3) _cell_angle_gamma 90.00 _cell_volume 3468.9(18) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3536 _cell_measurement_theta_min 4.07 _cell_measurement_theta_max 41.78 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.898 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1926 _exptl_absorpt_coefficient_mu 4.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5782 _exptl_absorpt_correction_T_max 0.8212 _exptl_absorpt_process_details '(Blessing 1951)' _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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54439 _diffrn_reflns_av_R_equivalents 0.1639 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7625 _reflns_number_gt 6628 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _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^)+(0.0555P)^2^+18.8126P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7625 _refine_ls_number_parameters 497 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1545 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.002 _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 Ir1 Ir 0.980585(17) 0.03800(3) 0.213362(14) 0.04038(12) Uani 1 1 d . . . N1 N 1.1045(4) 0.0529(6) 0.1895(3) 0.0448(14) Uani 1 1 d . . . N2 N 1.0198(4) 0.2145(6) 0.2626(3) 0.0407(13) Uani 1 1 d . . . C1 C 1.1497(5) -0.0420(7) 0.1659(4) 0.0477(17) Uani 1 1 d . . . H1A H 1.1274 -0.1244 0.1608 0.057 Uiso 1 1 calc R . . C2 C 1.2282(5) -0.0200(9) 0.1490(5) 0.055(2) Uani 1 1 d . . . H2A H 1.2604 -0.0877 0.1336 0.066 Uiso 1 1 calc R . . C3 C 1.2596(5) 0.0999(9) 0.1546(5) 0.055(2) Uani 1 1 d . . . H3A H 1.3128 0.1167 0.1414 0.066 Uiso 1 1 calc R . . C4 C 1.2137(6) 0.1940(9) 0.1793(5) 0.056(2) Uani 1 1 d . . . H4A H 1.2351 0.2770 0.1842 0.067 Uiso 1 1 calc R . . C5 C 1.1354(5) 0.1690(8) 0.1974(4) 0.0444(16) Uani 1 1 d . . . C6 C 1.0844(5) 0.2627(7) 0.2314(4) 0.0438(16) Uani 1 1 d . . . C7 C 1.0997(5) 0.3926(8) 0.2306(4) 0.0484(17) Uani 1 1 d . . . H7A H 1.1445 0.4251 0.2077 0.058 Uiso 1 1 calc R . . C8 C 1.0490(6) 0.4729(7) 0.2636(5) 0.0522(19) Uani 1 1 d . . . H8A H 1.0559 0.5620 0.2606 0.063 Uiso 1 1 calc R . . C9 C 0.9889(6) 0.4239(8) 0.3006(5) 0.0506(19) Uani 1 1 d . . . H9A H 0.9553 0.4780 0.3257 0.061 Uiso 1 1 calc R . . C10 C 0.9771(5) 0.2908(7) 0.3011(4) 0.0439(16) Uani 1 1 d . . . C11 C 0.9189(5) 0.2373(8) 0.3492(4) 0.0481(18) Uani 1 1 d . . . C12 C 0.8393(6) 0.2773(9) 0.3500(5) 0.057(2) Uani 1 1 d . . . H12A H 0.8196 0.3359 0.3169 0.068 Uiso 1 1 calc R . . C13 C 0.7885(6) 0.2320(10) 0.3989(5) 0.065(2) Uani 1 1 d . . . H13A H 0.7341 0.2588 0.3993 0.077 Uiso 1 1 calc R . . C14 C 0.8187(7) 0.1465(10) 0.4473(5) 0.066(3) Uani 1 1 d . . . H14A H 0.7841 0.1145 0.4805 0.079 Uiso 1 1 calc R . . C15 C 0.8980(7) 0.1072(9) 0.4479(5) 0.060(2) Uani 1 1 d . . . H15A H 0.9174 0.0497 0.4817 0.072 Uiso 1 1 calc R . . C16 C 0.9493(6) 0.1518(9) 0.3991(4) 0.054(2) Uani 1 1 d . . . H16A H 1.0038 0.1253 0.3992 0.065 Uiso 1 1 calc R . . N3 N 0.9947(5) -0.0767(7) 0.2950(4) 0.0490(15) Uani 1 1 d . . . N4 N 0.9240(4) -0.1106(7) 0.3241(3) 0.0479(15) Uani 1 1 d . . . C17 C 1.0537(5) -0.1334(8) 0.3293(4) 0.0503(19) Uani 1 1 d . . . H17A H 1.1091 -0.1263 0.3200 0.060 Uiso 1 1 calc R . . C18 C 1.0220(6) -0.2059(9) 0.3814(5) 0.059(2) Uani 1 1 d . . . H18A H 1.0515 -0.2572 0.4130 0.071 Uiso 1 1 calc R . . C19 C 0.9393(6) -0.1887(8) 0.3783(4) 0.054(2) Uani 1 1 d . . . H19A H 0.9013 -0.2238 0.4078 0.064 Uiso 1 1 calc R . . C20 C 0.8535(5) -0.0544(8) 0.2965(4) 0.0472(17) Uani 1 1 d . . . C21 C 0.8652(5) 0.0273(7) 0.2433(5) 0.0477(18) Uani 1 1 d . . . C22 C 0.7980(5) 0.0879(8) 0.2130(4) 0.0472(17) Uani 1 1 d . . . H22A H 0.8028 0.1388 0.1736 0.057 Uiso 1 1 calc R . . C23 C 0.7249(5) 0.0710(9) 0.2425(5) 0.054(2) Uani 1 1 d . . . C24 C 0.7117(5) -0.0086(9) 0.2966(5) 0.054(2) Uani 1 1 d . . . H24A H 0.6600 -0.0203 0.3145 0.065 Uiso 1 1 calc R . . C25 C 0.7789(6) -0.0699(8) 0.3229(5) 0.0529(19) Uani 1 1 d . . . F1 F 0.6595(3) 0.1321(5) 0.2152(3) 0.0652(14) Uani 1 1 d . . . F2 F 0.7699(3) -0.1468(5) 0.3776(3) 0.0627(13) Uani 1 1 d . . . N5 N 0.9516(4) 0.1392(6) 0.1290(3) 0.0432(14) Uani 1 1 d . . . N6 N 0.9245(4) 0.0708(6) 0.0747(3) 0.0438(14) Uani 1 1 d . . . C26 C 0.9407(5) 0.2600(7) 0.1139(4) 0.0459(17) Uani 1 1 d . . . H26A H 0.9541 0.3293 0.1429 0.055 Uiso 1 1 calc R . . C27 C 0.9054(6) 0.2693(8) 0.0469(4) 0.053(2) Uani 1 1 d . . . H27A H 0.8916 0.3444 0.0227 0.064 Uiso 1 1 calc R . . C28 C 0.8959(5) 0.1487(9) 0.0253(4) 0.0517(19) Uani 1 1 d . . . H28A H 0.8730 0.1231 -0.0173 0.062 Uiso 1 1 calc R . . C29 C 0.9287(5) -0.0638(7) 0.0831(4) 0.0433(16) Uani 1 1 d . . . C30 C 0.9529(4) -0.1054(7) 0.1480(4) 0.0433(16) Uani 1 1 d . . . C31 C 0.9600(5) -0.2347(7) 0.1587(4) 0.0457(17) Uani 1 1 d . . . H31A H 0.9759 -0.2668 0.2021 0.055 Uiso 1 1 calc R . . C32 C 0.9438(5) -0.3155(8) 0.1057(5) 0.0512(19) Uani 1 1 d . . . C33 C 0.9177(5) -0.2762(8) 0.0415(4) 0.0508(19) Uani 1 1 d . . . H33A H 0.9050 -0.3345 0.0061 0.061 Uiso 1 1 calc R . . C34 C 0.9116(5) -0.1477(8) 0.0326(4) 0.0487(18) Uani 1 1 d . . . F3 F 0.9523(4) -0.4431(5) 0.1165(3) 0.0623(14) Uani 1 1 d . . . F4 F 0.8892(4) -0.1064(5) -0.0305(3) 0.0638(13) Uani 1 1 d . . . P1 P 1.25334(16) 0.6001(2) 0.11563(13) 0.0584(6) Uani 1 1 d . . . F10 F 1.1812(4) 0.6508(6) 0.1600(4) 0.086(2) Uani 1 1 d . . . F11 F 1.1932(5) 0.5002(7) 0.0808(4) 0.091(2) Uani 1 1 d . . . F12 F 1.2734(4) 0.5009(6) 0.1748(3) 0.0677(15) Uani 1 1 d . . . F13 F 1.3130(4) 0.6989(6) 0.1510(3) 0.0721(16) Uani 1 1 d . . . F14 F 1.2328(5) 0.7030(8) 0.0593(4) 0.104(3) Uani 1 1 d . . . F15 F 1.3263(5) 0.5476(8) 0.0746(4) 0.095(2) Uani 1 1 d . . . C100 C 1.1347(16) 0.515(2) 0.5127(10) 0.116(8) Uani 0.75 1 d P . . H10A H 1.1574 0.5918 0.4923 0.140 Uiso 0.75 1 calc PR . . H10B H 1.0965 0.5426 0.5469 0.140 Uiso 0.75 1 calc PR . . Cl1 Cl 1.2053(4) 0.4416(5) 0.5508(3) 0.1101(17) Uani 0.75 1 d P . . Cl2 Cl 1.0814(3) 0.4349(6) 0.4503(3) 0.1146(18) Uani 0.75 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 0.04415(18) 0.03178(16) 0.04517(18) 0.00109(11) 0.00118(11) 0.00032(11) N1 0.042(3) 0.040(3) 0.052(4) 0.003(3) 0.003(3) 0.001(3) N2 0.049(4) 0.033(3) 0.040(3) 0.001(2) -0.002(3) 0.003(2) C1 0.050(4) 0.035(4) 0.058(4) 0.001(3) 0.000(4) 0.007(3) C2 0.050(5) 0.048(5) 0.066(5) -0.002(4) 0.008(4) 0.005(4) C3 0.046(4) 0.055(5) 0.063(5) 0.003(4) 0.007(4) 0.001(4) C4 0.056(5) 0.045(5) 0.067(5) 0.000(4) 0.007(4) -0.008(4) C5 0.047(4) 0.041(4) 0.045(4) 0.003(3) 0.000(3) -0.003(3) C6 0.044(4) 0.037(4) 0.050(4) 0.002(3) 0.000(3) 0.001(3) C7 0.046(4) 0.042(4) 0.058(4) 0.002(4) 0.001(3) -0.001(3) C8 0.060(5) 0.029(4) 0.067(5) 0.002(3) 0.003(4) -0.004(3) C9 0.056(5) 0.030(4) 0.066(5) -0.007(3) 0.003(4) 0.002(3) C10 0.051(4) 0.036(4) 0.045(4) -0.001(3) 0.000(3) -0.002(3) C11 0.055(5) 0.038(4) 0.051(4) -0.004(3) 0.002(4) -0.003(3) C12 0.064(5) 0.051(5) 0.056(5) 0.000(4) 0.013(4) 0.002(4) C13 0.060(6) 0.058(6) 0.078(6) -0.005(5) 0.018(5) 0.003(4) C14 0.081(7) 0.051(5) 0.066(6) -0.006(4) 0.022(5) -0.008(5) C15 0.082(7) 0.048(5) 0.051(5) 0.007(4) 0.003(4) 0.001(5) C16 0.066(5) 0.048(5) 0.047(4) -0.002(4) 0.006(4) -0.006(4) N3 0.055(4) 0.038(3) 0.054(4) 0.002(3) -0.001(3) -0.008(3) N4 0.057(4) 0.042(4) 0.045(3) 0.005(3) -0.002(3) -0.002(3) C17 0.055(5) 0.038(4) 0.057(5) 0.009(3) -0.010(4) 0.001(3) C18 0.067(6) 0.048(5) 0.061(5) 0.013(4) -0.003(4) -0.002(4) C19 0.064(5) 0.044(4) 0.053(5) 0.009(4) 0.001(4) -0.005(4) C20 0.046(4) 0.037(4) 0.058(4) 0.000(3) -0.002(3) -0.002(3) C21 0.041(4) 0.036(4) 0.066(5) -0.003(3) 0.007(3) -0.004(3) C22 0.047(4) 0.038(4) 0.056(4) -0.002(3) -0.001(3) -0.004(3) C23 0.044(4) 0.047(5) 0.072(6) -0.007(4) -0.004(4) 0.005(3) C24 0.049(5) 0.049(5) 0.064(5) -0.004(4) 0.010(4) -0.003(4) C25 0.061(5) 0.040(4) 0.057(5) 0.000(4) -0.001(4) -0.010(4) F1 0.048(3) 0.053(3) 0.095(4) 0.008(3) 0.003(3) 0.006(2) F2 0.066(3) 0.058(3) 0.065(3) 0.013(2) 0.015(3) -0.008(3) N5 0.048(4) 0.040(3) 0.042(3) 0.001(3) 0.002(3) 0.004(3) N6 0.045(3) 0.041(3) 0.045(3) 0.002(3) 0.004(3) 0.004(3) C26 0.049(4) 0.031(4) 0.058(4) 0.013(3) 0.008(3) 0.009(3) C27 0.062(5) 0.043(4) 0.055(5) 0.007(4) 0.002(4) 0.005(4) C28 0.055(5) 0.053(5) 0.048(4) 0.008(4) 0.004(4) -0.001(4) C29 0.045(4) 0.033(4) 0.052(4) 0.000(3) 0.010(3) 0.000(3) C30 0.040(4) 0.038(4) 0.053(4) -0.002(3) 0.004(3) -0.002(3) C31 0.048(4) 0.037(4) 0.053(4) 0.001(3) 0.000(3) -0.002(3) C32 0.048(4) 0.040(4) 0.067(5) 0.001(4) 0.010(4) 0.002(3) C33 0.061(5) 0.035(4) 0.057(5) -0.007(3) 0.012(4) -0.005(3) C34 0.048(4) 0.049(5) 0.050(4) 0.000(3) 0.002(3) -0.002(3) F3 0.080(4) 0.032(2) 0.076(3) -0.005(2) 0.011(3) 0.000(2) F4 0.080(4) 0.059(3) 0.052(3) -0.002(2) -0.009(2) -0.001(3) P1 0.0674(15) 0.0439(12) 0.0632(13) 0.0019(10) -0.0090(11) -0.0024(10) F10 0.066(4) 0.057(4) 0.137(6) -0.003(4) 0.003(4) 0.018(3) F11 0.095(5) 0.062(4) 0.114(6) -0.016(4) -0.017(4) -0.021(4) F12 0.063(3) 0.053(3) 0.087(4) 0.018(3) 0.005(3) 0.004(3) F13 0.084(4) 0.056(3) 0.075(4) -0.001(3) -0.022(3) -0.010(3) F14 0.122(6) 0.087(5) 0.101(5) 0.039(4) -0.054(5) -0.024(4) F15 0.104(5) 0.099(6) 0.083(4) -0.017(4) 0.029(4) -0.015(4) C100 0.15(2) 0.130(19) 0.067(10) -0.014(11) 0.008(12) -0.002(16) Cl1 0.114(4) 0.076(3) 0.138(4) -0.001(3) -0.025(3) 0.015(3) Cl2 0.089(3) 0.136(5) 0.118(4) -0.054(4) -0.002(3) 0.000(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 N3 2.021(7) . ? Ir1 N5 2.022(6) . ? Ir1 C30 2.031(8) . ? Ir1 C21 2.035(8) . ? Ir1 N1 2.140(7) . ? Ir1 N2 2.191(6) . ? N1 C5 1.337(10) . ? N1 C1 1.346(10) . ? N2 C10 1.331(10) . ? N2 C6 1.356(10) . ? C1 C2 1.380(12) . ? C1 H1A 0.9500 . ? C2 C3 1.374(13) . ? C2 H2A 0.9500 . ? C3 C4 1.354(13) . ? C3 H3A 0.9500 . ? C4 C5 1.391(12) . ? C4 H4A 0.9500 . ? C5 C6 1.479(11) . ? C6 C7 1.396(11) . ? C7 C8 1.378(12) . ? C7 H7A 0.9500 . ? C8 C9 1.362(13) . ? C8 H8A 0.9500 . ? C9 C10 1.420(11) . ? C9 H9A 0.9500 . ? C10 C11 1.491(11) . ? C11 C12 1.392(13) . ? C11 C16 1.416(12) . ? C12 C13 1.391(13) . ? C12 H12A 0.9500 . ? C13 C14 1.395(15) . ? C13 H13A 0.9500 . ? C14 C15 1.385(15) . ? C14 H14A 0.9500 . ? C15 C16 1.392(13) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? N3 C17 1.318(11) . ? N3 N4 1.375(10) . ? N4 C19 1.368(10) . ? N4 C20 1.409(11) . ? C17 C18 1.401(12) . ? C17 H17A 0.9500 . ? C18 C19 1.388(14) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C25 1.374(12) . ? C20 C21 1.377(12) . ? C21 C22 1.404(12) . ? C22 C23 1.381(12) . ? C22 H22A 0.9500 . ? C23 F1 1.361(10) . ? C23 C24 1.382(14) . ? C24 C25 1.378(13) . ? C24 H24A 0.9500 . ? C25 F2 1.364(10) . ? N5 C26 1.321(10) . ? N5 N6 1.357(9) . ? N6 C28 1.349(11) . ? N6 C29 1.433(10) . ? C26 C27 1.432(12) . ? C26 H26A 0.9500 . ? C27 C28 1.350(13) . ? C27 H27A 0.9500 . ? C28 H28A 0.9500 . ? C29 C34 1.355(12) . ? C29 C30 1.399(11) . ? C30 C31 1.387(11) . ? C31 C32 1.367(12) . ? C31 H31A 0.9500 . ? C32 F3 1.372(10) . ? C32 C33 1.388(13) . ? C33 C34 1.372(12) . ? C33 H33A 0.9500 . ? C34 F4 1.359(10) . ? P1 F14 1.582(7) . ? P1 F15 1.583(8) . ? P1 F13 1.586(6) . ? P1 F11 1.594(7) . ? P1 F12 1.595(6) . ? P1 F10 1.602(7) . ? C100 Cl1 1.58(3) . ? C100 Cl2 1.71(2) . ? C100 H10A 0.9900 . ? C100 H10B 0.9900 . ? 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 N3 Ir1 N5 171.8(3) . . ? N3 Ir1 C30 94.4(3) . . ? N5 Ir1 C30 80.2(3) . . ? N3 Ir1 C21 79.6(3) . . ? N5 Ir1 C21 93.9(3) . . ? C30 Ir1 C21 86.9(3) . . ? N3 Ir1 N1 97.7(3) . . ? N5 Ir1 N1 89.1(3) . . ? C30 Ir1 N1 96.6(3) . . ? C21 Ir1 N1 175.7(3) . . ? N3 Ir1 N2 97.6(3) . . ? N5 Ir1 N2 88.5(2) . . ? C30 Ir1 N2 166.7(3) . . ? C21 Ir1 N2 100.9(3) . . ? N1 Ir1 N2 76.1(2) . . ? C5 N1 C1 120.4(7) . . ? C5 N1 Ir1 114.3(5) . . ? C1 N1 Ir1 125.2(6) . . ? C10 N2 C6 118.7(7) . . ? C10 N2 Ir1 127.6(5) . . ? C6 N2 Ir1 110.3(5) . . ? N1 C1 C2 120.3(8) . . ? N1 C1 H1A 119.9 . . ? C2 C1 H1A 119.9 . . ? C3 C2 C1 119.8(8) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C4 C3 C2 119.2(8) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 120.0(8) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? N1 C5 C4 120.3(8) . . ? N1 C5 C6 116.2(7) . . ? C4 C5 C6 123.3(8) . . ? N2 C6 C7 121.5(7) . . ? N2 C6 C5 115.6(7) . . ? C7 C6 C5 122.9(7) . . ? C8 C7 C6 119.0(8) . . ? C8 C7 H7A 120.5 . . ? C6 C7 H7A 120.5 . . ? C9 C8 C7 119.6(8) . . ? C9 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C8 C9 C10 118.9(8) . . ? C8 C9 H9A 120.5 . . ? C10 C9 H9A 120.5 . . ? N2 C10 C9 121.3(8) . . ? N2 C10 C11 120.5(7) . . ? C9 C10 C11 118.1(7) . . ? C12 C11 C16 120.2(8) . . ? C12 C11 C10 122.2(8) . . ? C16 C11 C10 117.3(8) . . ? C13 C12 C11 120.5(9) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C14 118.9(9) . . ? C12 C13 H13A 120.6 . . ? C14 C13 H13A 120.6 . . ? C15 C14 C13 121.4(9) . . ? C15 C14 H14A 119.3 . . ? C13 C14 H14A 119.3 . . ? C14 C15 C16 120.1(9) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C15 C16 C11 118.8(9) . . ? C15 C16 H16A 120.6 . . ? C11 C16 H16A 120.6 . . ? C17 N3 N4 107.6(7) . . ? C17 N3 Ir1 138.1(6) . . ? N4 N3 Ir1 114.3(5) . . ? C19 N4 N3 110.2(7) . . ? C19 N4 C20 133.4(8) . . ? N3 N4 C20 116.3(7) . . ? N3 C17 C18 109.3(8) . . ? N3 C17 H17A 125.3 . . ? C18 C17 H17A 125.3 . . ? C19 C18 C17 107.2(8) . . ? C19 C18 H18A 126.4 . . ? C17 C18 H18A 126.4 . . ? N4 C19 C18 105.7(8) . . ? N4 C19 H19A 127.1 . . ? C18 C19 H19A 127.1 . . ? C25 C20 C21 121.1(8) . . ? C25 C20 N4 123.9(8) . . ? C21 C20 N4 114.8(7) . . ? C20 C21 C22 118.6(8) . . ? C20 C21 Ir1 114.6(6) . . ? C22 C21 Ir1 126.7(7) . . ? C23 C22 C21 117.6(8) . . ? C23 C22 H22A 121.2 . . ? C21 C22 H22A 121.2 . . ? F1 C23 C22 118.5(9) . . ? F1 C23 C24 116.7(8) . . ? C22 C23 C24 124.8(8) . . ? C25 C24 C23 115.3(8) . . ? C25 C24 H24A 122.3 . . ? C23 C24 H24A 122.3 . . ? F2 C25 C20 119.8(8) . . ? F2 C25 C24 117.8(8) . . ? C20 C25 C24 122.4(8) . . ? C26 N5 N6 107.3(7) . . ? C26 N5 Ir1 136.3(6) . . ? N6 N5 Ir1 115.6(5) . . ? C28 N6 N5 110.2(7) . . ? C28 N6 C29 134.7(7) . . ? N5 N6 C29 115.0(6) . . ? N5 C26 C27 108.8(8) . . ? N5 C26 H26A 125.6 . . ? C27 C26 H26A 125.6 . . ? C28 C27 C26 105.5(8) . . ? C28 C27 H27A 127.3 . . ? C26 C27 H27A 127.3 . . ? N6 C28 C27 108.2(8) . . ? N6 C28 H28A 125.9 . . ? C27 C28 H28A 125.9 . . ? C34 C29 C30 120.9(7) . . ? C34 C29 N6 123.7(8) . . ? C30 C29 N6 115.4(7) . . ? C31 C30 C29 117.9(7) . . ? C31 C30 Ir1 128.5(6) . . ? C29 C30 Ir1 113.5(6) . . ? C32 C31 C30 119.0(8) . . ? C32 C31 H31A 120.5 . . ? C30 C31 H31A 120.5 . . ? C31 C32 F3 118.6(8) . . ? C31 C32 C33 123.9(8) . . ? F3 C32 C33 117.5(8) . . ? C34 C33 C32 115.6(8) . . ? C34 C33 H33A 122.2 . . ? C32 C33 H33A 122.2 . . ? C29 C34 F4 120.5(8) . . ? C29 C34 C33 122.6(8) . . ? F4 C34 C33 116.9(8) . . ? F14 P1 F15 91.9(5) . . ? F14 P1 F13 88.5(4) . . ? F15 P1 F13 88.6(4) . . ? F14 P1 F11 92.0(4) . . ? F15 P1 F11 91.7(4) . . ? F13 P1 F11 179.4(4) . . ? F14 P1 F12 177.5(5) . . ? F15 P1 F12 89.9(4) . . ? F13 P1 F12 89.9(3) . . ? F11 P1 F12 89.6(4) . . ? F14 P1 F10 90.3(5) . . ? F15 P1 F10 177.6(4) . . ? F13 P1 F10 90.6(4) . . ? F11 P1 F10 89.1(4) . . ? F12 P1 F10 87.8(4) . . ? Cl1 C100 Cl2 117.5(15) . . ? Cl1 C100 H10A 107.9 . . ? Cl2 C100 H10A 107.9 . . ? Cl1 C100 H10B 107.9 . . ? Cl2 C100 H10B 107.9 . . ? H10A C100 H10B 107.2 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.197 _refine_diff_density_min -1.904 _refine_diff_density_rms 0.250 data_gs52 _database_code_depnum_ccdc_archive 'CCDC 890057' #TrackingRef 'GS52_dimer.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H20 Cl2 F8 Ir2 N8, C H2 Cl2' _chemical_formula_sum 'C37 H22 Cl4 F8 Ir2 N8' _chemical_formula_weight 1256.87 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.753(3) _cell_length_b 12.323(4) _cell_length_c 16.058(4) _cell_angle_alpha 80.37(2) _cell_angle_beta 84.700(19) _cell_angle_gamma 65.47(2) _cell_volume 1907.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1745 _cell_measurement_theta_min 6.56 _cell_measurement_theta_max 69.06 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 7.329 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3219 _exptl_absorpt_correction_T_max 0.7107 _exptl_absorpt_process_details '(Blessing 1951)' _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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20996 _diffrn_reflns_av_R_equivalents 0.0755 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.00 _reflns_number_total 8332 _reflns_number_gt 7239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _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^)+(0.0578P)^2^+0.7745P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8332 _refine_ls_number_parameters 532 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.40124(2) 0.326742(18) 0.272104(13) 0.01737(7) Uani 1 1 d . . . Ir2 Ir 0.75175(2) 0.098016(18) 0.237263(12) 0.01692(7) Uani 1 1 d . . . Cl1 Cl 0.51288(14) 0.11160(13) 0.24814(9) 0.0229(3) Uani 1 1 d . . . Cl2 Cl 0.63709(14) 0.31713(13) 0.24709(10) 0.0236(3) Uani 1 1 d . . . N1 N 0.3599(5) 0.3803(5) 0.1476(3) 0.0225(10) Uani 1 1 d . . . N2 N 0.2351(5) 0.3902(5) 0.1266(3) 0.0221(10) Uani 1 1 d . . . F1 F -0.0823(4) 0.3296(5) 0.4026(3) 0.0490(12) Uani 1 1 d . . . F2 F -0.0365(5) 0.4168(4) 0.1096(3) 0.0426(10) Uani 1 1 d . . . C1 C 0.4221(8) 0.4041(6) 0.0770(4) 0.0307(14) Uani 1 1 d . . . H1A H 0.5107 0.4044 0.0731 0.037 Uiso 1 1 calc R . . C2 C 0.3376(9) 0.4293(8) 0.0078(5) 0.0450(19) Uani 1 1 d . . . H2A H 0.3578 0.4489 -0.0502 0.054 Uiso 1 1 calc R . . C3 C 0.2219(9) 0.4196(8) 0.0415(5) 0.0407(17) Uani 1 1 d . . . H3A H 0.1448 0.4313 0.0109 0.049 Uiso 1 1 calc R . . C4 C 0.1516(6) 0.3716(5) 0.1953(4) 0.0218(11) Uani 1 1 d . . . C5 C 0.2082(6) 0.3428(5) 0.2753(4) 0.0206(11) Uani 1 1 d . . . C6 C 0.1270(6) 0.3293(6) 0.3455(4) 0.0243(12) Uani 1 1 d . . . H6A H 0.1621 0.3096 0.4007 0.029 Uiso 1 1 calc R . . C7 C -0.0038(6) 0.3447(6) 0.3338(5) 0.0301(14) Uani 1 1 d . . . C8 C -0.0637(6) 0.3740(6) 0.2566(5) 0.0307(14) Uani 1 1 d . . . H8A H -0.1551 0.3838 0.2511 0.037 Uiso 1 1 calc R . . C9 C 0.0169(7) 0.3883(6) 0.1876(4) 0.0273(13) Uani 1 1 d . . . N3 N 0.4209(5) 0.2813(5) 0.3993(3) 0.0244(10) Uani 1 1 d . . . N4 N 0.3871(6) 0.3768(6) 0.4420(4) 0.0347(13) Uani 1 1 d . . . F3 F 0.2261(7) 0.8095(4) 0.2341(5) 0.0743(19) Uani 1 1 d . . . F4 F 0.3346(6) 0.5925(6) 0.5057(4) 0.0646(17) Uani 1 1 d . . . C10 C 0.4425(7) 0.1851(8) 0.4558(4) 0.0378(16) Uani 1 1 d . . . H10A H 0.4662 0.1063 0.4428 0.045 Uiso 1 1 calc R . . C11 C 0.4259(10) 0.2143(10) 0.5360(5) 0.053(2) Uani 1 1 d . . . H11A H 0.4386 0.1607 0.5875 0.064 Uiso 1 1 calc R . . C12 C 0.3876(9) 0.3362(11) 0.5268(5) 0.052(2) Uani 1 1 d . . . H12A H 0.3653 0.3840 0.5712 0.063 Uiso 1 1 calc R . . C13 C 0.3466(7) 0.4897(7) 0.3915(5) 0.0326(15) Uani 1 1 d . . . C14 C 0.3378(6) 0.4900(6) 0.3045(4) 0.0250(12) Uani 1 1 d . . . C15 C 0.2965(7) 0.5997(6) 0.2515(5) 0.0304(14) Uani 1 1 d . . . H15A H 0.2882 0.6035 0.1926 0.036 Uiso 1 1 calc R . . C16 C 0.2677(9) 0.7032(7) 0.2864(6) 0.047(2) Uani 1 1 d . . . C17 C 0.2775(10) 0.7043(8) 0.3706(7) 0.055(2) Uani 1 1 d . . . H17A H 0.2563 0.7772 0.3924 0.066 Uiso 1 1 calc R . . C18 C 0.3195(9) 0.5954(8) 0.4221(6) 0.046(2) Uani 1 1 d . . . N5 N 0.7747(5) 0.0546(5) 0.3632(3) 0.0214(10) Uani 1 1 d . . . N6 N 0.8340(6) -0.0663(5) 0.3916(3) 0.0261(11) Uani 1 1 d . . . F5 F 0.9552(6) -0.3419(4) 0.1361(3) 0.0486(12) Uani 1 1 d . . . F6 F 0.9460(5) -0.3218(4) 0.4252(3) 0.0451(11) Uani 1 1 d . . . C19 C 0.7617(7) 0.1115(7) 0.4286(4) 0.0311(14) Uani 1 1 d . . . H19A H 0.7228 0.1964 0.4277 0.037 Uiso 1 1 calc R . . C20 C 0.8153(9) 0.0249(8) 0.4998(5) 0.0404(17) Uani 1 1 d . . . H20A H 0.8200 0.0406 0.5551 0.049 Uiso 1 1 calc R . . C21 C 0.8589(8) -0.0851(8) 0.4749(5) 0.0404(17) Uani 1 1 d . . . H21A H 0.8992 -0.1609 0.5094 0.048 Uiso 1 1 calc R . . C22 C 0.8648(6) -0.1420(6) 0.3289(4) 0.0240(12) Uani 1 1 d . . . C23 C 0.8357(6) -0.0816(5) 0.2451(4) 0.0211(11) Uani 1 1 d . . . C24 C 0.8662(6) -0.1517(6) 0.1812(4) 0.0266(13) Uani 1 1 d . . . H24A H 0.8477 -0.1148 0.1243 0.032 Uiso 1 1 calc R . . C25 C 0.9239(7) -0.2758(6) 0.2006(4) 0.0298(13) Uani 1 1 d . . . C26 C 0.9518(8) -0.3355(6) 0.2814(5) 0.0359(15) Uani 1 1 d . . . H26A H 0.9914 -0.4211 0.2928 0.043 Uiso 1 1 calc R . . N7 N 0.7533(6) 0.1322(5) 0.1097(3) 0.0230(10) Uani 1 1 d . . . N8 N 0.8676(6) 0.1433(5) 0.0737(3) 0.0256(11) Uani 1 1 d . . . F7 F 1.2622(4) 0.0348(4) 0.3050(3) 0.0405(10) Uani 1 1 d . . . F8 F 1.1248(5) 0.1515(5) 0.0240(3) 0.0425(11) Uani 1 1 d . . . C27 C 0.9198(7) -0.2660(6) 0.3447(5) 0.0325(14) Uani 1 1 d . . . C28 C 0.6742(7) 0.1455(6) 0.0477(4) 0.0279(13) Uani 1 1 d . . . H28A H 0.5885 0.1394 0.0549 0.033 Uiso 1 1 calc R . . C29 C 0.7336(8) 0.1696(8) -0.0301(4) 0.0399(18) Uani 1 1 d . . . H29A H 0.6969 0.1845 -0.0845 0.048 Uiso 1 1 calc R . . C30 C 0.8559(8) 0.1673(8) -0.0112(4) 0.0369(16) Uani 1 1 d . . . H30A H 0.9214 0.1802 -0.0508 0.044 Uiso 1 1 calc R . . C31 C 0.9709(6) 0.1217(6) 0.1310(4) 0.0225(11) Uani 1 1 d . . . C32 C 0.9387(6) 0.0943(5) 0.2167(4) 0.0185(10) Uani 1 1 d . . . C33 C 1.0383(6) 0.0682(5) 0.2743(4) 0.0219(11) Uani 1 1 d . . . H33A H 1.0203 0.0509 0.3329 0.026 Uiso 1 1 calc R . . C34 C 1.1632(6) 0.0673(6) 0.2469(4) 0.0245(12) Uani 1 1 d . . . C35 C 1.1975(7) 0.0954(6) 0.1636(5) 0.0284(13) Uani 1 1 d . . . H35A H 1.2845 0.0956 0.1470 0.034 Uiso 1 1 calc R . . C36 C 1.0972(7) 0.1231(6) 0.1058(4) 0.0285(13) Uani 1 1 d . . . C100 C 0.5509(10) 0.8240(9) 0.2034(6) 0.052(2) Uani 1 1 d . . . H10B H 0.6080 0.8495 0.2339 0.063 Uiso 1 1 calc R . . H10C H 0.4553 0.8627 0.2244 0.063 Uiso 1 1 calc R . . Cl10 Cl 0.5595(3) 0.8746(3) 0.09450(17) 0.0611(6) Uani 1 1 d . . . Cl11 Cl 0.6063(3) 0.6678(2) 0.2261(2) 0.0685(7) 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 Ir1 0.01320(11) 0.01930(12) 0.02036(12) -0.00094(8) -0.00266(8) -0.00760(9) Ir2 0.01335(12) 0.01920(12) 0.01873(11) -0.00088(8) -0.00216(8) -0.00747(9) Cl1 0.0162(6) 0.0222(7) 0.0323(7) -0.0025(6) -0.0026(5) -0.0097(5) Cl2 0.0147(6) 0.0226(7) 0.0355(7) -0.0054(6) -0.0005(5) -0.0091(5) N1 0.016(2) 0.019(2) 0.030(3) 0.004(2) -0.0069(19) -0.0058(19) N2 0.019(2) 0.026(3) 0.019(2) 0.0039(19) -0.0088(18) -0.008(2) F1 0.025(2) 0.068(3) 0.054(3) 0.010(2) 0.0056(19) -0.027(2) F2 0.038(2) 0.045(3) 0.046(2) 0.007(2) -0.026(2) -0.018(2) C1 0.038(4) 0.033(3) 0.019(3) 0.003(2) -0.003(3) -0.015(3) C2 0.048(5) 0.054(5) 0.027(3) 0.006(3) -0.002(3) -0.019(4) C3 0.046(4) 0.046(4) 0.027(3) 0.010(3) -0.019(3) -0.018(4) C4 0.018(3) 0.015(3) 0.029(3) -0.003(2) -0.006(2) -0.003(2) C5 0.010(2) 0.016(3) 0.035(3) -0.003(2) -0.003(2) -0.005(2) C6 0.021(3) 0.024(3) 0.027(3) 0.002(2) -0.001(2) -0.011(2) C7 0.015(3) 0.028(3) 0.043(4) 0.005(3) -0.001(3) -0.009(2) C8 0.014(3) 0.026(3) 0.052(4) 0.004(3) -0.011(3) -0.009(2) C9 0.025(3) 0.021(3) 0.033(3) 0.007(2) -0.016(3) -0.007(2) N3 0.016(2) 0.030(3) 0.025(2) 0.000(2) -0.0057(19) -0.008(2) N4 0.032(3) 0.053(4) 0.023(3) -0.013(3) 0.002(2) -0.020(3) F3 0.093(5) 0.024(2) 0.095(5) -0.010(3) 0.025(4) -0.018(3) F4 0.072(4) 0.090(4) 0.055(3) -0.048(3) 0.021(3) -0.047(3) C10 0.024(3) 0.053(5) 0.029(3) 0.011(3) -0.007(3) -0.013(3) C11 0.049(5) 0.075(7) 0.033(4) 0.012(4) -0.003(3) -0.028(5) C12 0.044(5) 0.096(8) 0.024(3) -0.010(4) -0.001(3) -0.035(5) C13 0.023(3) 0.044(4) 0.039(4) -0.017(3) 0.004(3) -0.019(3) C14 0.014(3) 0.028(3) 0.035(3) -0.010(3) 0.005(2) -0.010(2) C15 0.024(3) 0.024(3) 0.043(4) -0.004(3) 0.003(3) -0.010(3) C16 0.053(5) 0.031(4) 0.062(5) -0.014(4) 0.019(4) -0.024(4) C17 0.050(5) 0.042(5) 0.078(7) -0.035(5) 0.025(5) -0.019(4) C18 0.046(5) 0.058(5) 0.051(5) -0.035(4) 0.018(4) -0.032(4) N5 0.016(2) 0.019(2) 0.025(2) 0.0019(19) -0.0031(19) -0.0046(19) N6 0.026(3) 0.030(3) 0.022(2) 0.003(2) -0.003(2) -0.014(2) F5 0.067(3) 0.029(2) 0.045(3) -0.014(2) 0.004(2) -0.013(2) F6 0.058(3) 0.033(2) 0.036(2) 0.0130(18) -0.014(2) -0.014(2) C19 0.031(3) 0.038(4) 0.027(3) -0.004(3) -0.006(3) -0.015(3) C20 0.047(4) 0.049(5) 0.026(3) -0.002(3) -0.013(3) -0.019(4) C21 0.040(4) 0.046(4) 0.031(3) 0.006(3) -0.012(3) -0.015(4) C22 0.023(3) 0.024(3) 0.025(3) 0.000(2) -0.001(2) -0.011(2) C23 0.015(3) 0.025(3) 0.026(3) 0.000(2) -0.001(2) -0.011(2) C24 0.020(3) 0.027(3) 0.034(3) -0.001(3) 0.002(2) -0.013(3) C25 0.025(3) 0.025(3) 0.037(3) -0.006(3) 0.000(3) -0.007(3) C26 0.031(4) 0.024(3) 0.048(4) 0.003(3) -0.005(3) -0.009(3) N7 0.028(3) 0.026(3) 0.020(2) -0.002(2) -0.001(2) -0.016(2) N8 0.024(3) 0.037(3) 0.021(2) -0.001(2) 0.001(2) -0.019(2) F7 0.023(2) 0.058(3) 0.041(2) 0.008(2) -0.0137(17) -0.021(2) F8 0.038(2) 0.067(3) 0.028(2) -0.003(2) 0.0083(17) -0.030(2) C27 0.028(3) 0.025(3) 0.039(4) 0.010(3) -0.008(3) -0.008(3) C28 0.029(3) 0.037(4) 0.021(3) 0.004(2) -0.010(2) -0.018(3) C29 0.037(4) 0.062(5) 0.022(3) 0.003(3) -0.008(3) -0.023(4) C30 0.036(4) 0.060(5) 0.019(3) 0.001(3) -0.005(3) -0.025(4) C31 0.018(3) 0.026(3) 0.025(3) -0.007(2) 0.000(2) -0.009(2) C32 0.014(2) 0.014(2) 0.025(3) -0.002(2) 0.003(2) -0.005(2) C33 0.019(3) 0.026(3) 0.023(3) -0.006(2) -0.001(2) -0.011(2) C34 0.013(3) 0.028(3) 0.030(3) 0.000(2) -0.005(2) -0.006(2) C35 0.019(3) 0.028(3) 0.040(4) -0.008(3) 0.006(3) -0.012(3) C36 0.028(3) 0.036(3) 0.025(3) -0.006(3) 0.007(2) -0.017(3) C100 0.041(5) 0.061(6) 0.063(6) -0.029(5) 0.013(4) -0.025(4) Cl10 0.0569(14) 0.0764(17) 0.0598(13) -0.0115(12) -0.0139(11) -0.0337(13) Cl11 0.0624(16) 0.0590(15) 0.0849(19) -0.0161(14) 0.0057(14) -0.0249(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C14 1.982(6) . ? Ir1 C5 1.999(5) . ? Ir1 N1 2.028(5) . ? Ir1 N3 2.032(5) . ? Ir1 Cl2 2.4870(15) . ? Ir1 Cl1 2.4962(17) . ? Ir2 C32 1.989(5) . ? Ir2 C23 2.000(6) . ? Ir2 N5 2.014(5) . ? Ir2 N7 2.022(5) . ? Ir2 Cl2 2.4856(17) . ? Ir2 Cl1 2.4951(15) . ? N1 C1 1.315(8) . ? N1 N2 1.365(7) . ? N2 C3 1.359(8) . ? N2 C4 1.407(8) . ? F1 C7 1.363(8) . ? F2 C9 1.357(7) . ? C1 C2 1.412(10) . ? C1 H1A 0.9500 . ? C2 C3 1.354(12) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C9 1.389(8) . ? C4 C5 1.400(8) . ? C5 C6 1.392(8) . ? C6 C7 1.366(9) . ? C6 H6A 0.9500 . ? C7 C8 1.374(10) . ? C8 C9 1.376(10) . ? C8 H8A 0.9500 . ? N3 C10 1.317(9) . ? N3 N4 1.362(8) . ? N4 C12 1.370(10) . ? N4 C13 1.402(10) . ? F3 C16 1.355(11) . ? F4 C18 1.360(10) . ? C10 C11 1.371(12) . ? C10 H10A 0.9500 . ? C11 C12 1.368(15) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C18 1.376(10) . ? C13 C14 1.409(10) . ? C14 C15 1.391(10) . ? C15 C16 1.384(10) . ? C15 H15A 0.9500 . ? C16 C17 1.369(14) . ? C17 C18 1.372(14) . ? C17 H17A 0.9500 . ? N5 C19 1.324(8) . ? N5 N6 1.369(7) . ? N6 C21 1.350(9) . ? N6 C22 1.411(8) . ? F5 C25 1.357(8) . ? F6 C27 1.353(8) . ? C19 C20 1.407(10) . ? C19 H19A 0.9500 . ? C20 C21 1.355(12) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C27 1.377(9) . ? C22 C23 1.419(8) . ? C23 C24 1.379(9) . ? C24 C25 1.382(9) . ? C24 H24A 0.9500 . ? C25 C26 1.373(10) . ? C26 C27 1.367(11) . ? C26 H26A 0.9500 . ? N7 C28 1.315(8) . ? N7 N8 1.358(7) . ? N8 C30 1.352(8) . ? N8 C31 1.419(8) . ? F7 C34 1.367(7) . ? F8 C36 1.341(7) . ? C28 C29 1.394(9) . ? C28 H28A 0.9500 . ? C29 C30 1.364(10) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C31 C36 1.386(8) . ? C31 C32 1.408(8) . ? C32 C33 1.379(8) . ? C33 C34 1.369(8) . ? C33 H33A 0.9500 . ? C34 C35 1.381(9) . ? C35 C36 1.383(10) . ? C35 H35A 0.9500 . ? C100 Cl11 1.746(10) . ? C100 Cl10 1.763(11) . ? C100 H10B 0.9900 . ? C100 H10C 0.9900 . ? 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 90.3(2) . . ? C14 Ir1 N1 96.8(2) . . ? C5 Ir1 N1 80.5(2) . . ? C14 Ir1 N3 80.7(3) . . ? C5 Ir1 N3 93.9(2) . . ? N1 Ir1 N3 173.9(2) . . ? C14 Ir1 Cl2 90.27(17) . . ? C5 Ir1 Cl2 172.13(19) . . ? N1 Ir1 Cl2 91.62(15) . . ? N3 Ir1 Cl2 93.95(15) . . ? C14 Ir1 Cl1 170.34(19) . . ? C5 Ir1 Cl1 97.01(17) . . ? N1 Ir1 Cl1 90.66(15) . . ? N3 Ir1 Cl1 92.39(16) . . ? Cl2 Ir1 Cl1 83.39(5) . . ? C32 Ir2 C23 88.2(2) . . ? C32 Ir2 N5 93.1(2) . . ? C23 Ir2 N5 80.8(2) . . ? C32 Ir2 N7 80.6(2) . . ? C23 Ir2 N7 96.2(2) . . ? N5 Ir2 N7 173.2(2) . . ? C32 Ir2 Cl2 95.35(16) . . ? C23 Ir2 Cl2 172.49(17) . . ? N5 Ir2 Cl2 92.36(15) . . ? N7 Ir2 Cl2 90.95(16) . . ? C32 Ir2 Cl1 174.34(17) . . ? C23 Ir2 Cl1 93.69(16) . . ? N5 Ir2 Cl1 92.48(15) . . ? N7 Ir2 Cl1 93.84(15) . . ? Cl2 Ir2 Cl1 83.45(5) . . ? Ir2 Cl1 Ir1 96.10(5) . . ? Ir2 Cl2 Ir1 96.58(5) . . ? C1 N1 N2 107.1(5) . . ? C1 N1 Ir1 138.3(5) . . ? N2 N1 Ir1 114.4(4) . . ? C3 N2 N1 109.3(5) . . ? C3 N2 C4 135.6(6) . . ? N1 N2 C4 115.1(5) . . ? N1 C1 C2 109.9(6) . . ? N1 C1 H1A 125.0 . . ? C2 C1 H1A 125.0 . . ? C3 C2 C1 105.4(7) . . ? C3 C2 H2A 127.3 . . ? C1 C2 H2A 127.3 . . ? C2 C3 N2 108.2(6) . . ? C2 C3 H3A 125.9 . . ? N2 C3 H3A 125.9 . . ? C9 C4 C5 120.1(6) . . ? C9 C4 N2 123.7(6) . . ? C5 C4 N2 116.1(5) . . ? C6 C5 C4 118.2(5) . . ? C6 C5 Ir1 128.3(5) . . ? C4 C5 Ir1 113.5(4) . . ? C7 C6 C5 119.0(6) . . ? C7 C6 H6A 120.5 . . ? C5 C6 H6A 120.5 . . ? F1 C7 C6 118.8(6) . . ? F1 C7 C8 116.5(6) . . ? C6 C7 C8 124.7(6) . . ? C7 C8 C9 115.8(6) . . ? C7 C8 H8A 122.1 . . ? C9 C8 H8A 122.1 . . ? F2 C9 C8 118.5(6) . . ? F2 C9 C4 119.3(6) . . ? C8 C9 C4 122.2(6) . . ? C10 N3 N4 107.5(6) . . ? C10 N3 Ir1 137.7(5) . . ? N4 N3 Ir1 114.2(4) . . ? N3 N4 C12 108.3(7) . . ? N3 N4 C13 115.3(5) . . ? C12 N4 C13 135.9(7) . . ? N3 C10 C11 110.6(8) . . ? N3 C10 H10A 124.7 . . ? C11 C10 H10A 124.7 . . ? C12 C11 C10 106.1(7) . . ? C12 C11 H11A 127.0 . . ? C10 C11 H11A 127.0 . . ? C11 C12 N4 107.5(8) . . ? C11 C12 H12A 126.2 . . ? N4 C12 H12A 126.2 . . ? C18 C13 N4 124.0(7) . . ? C18 C13 C14 120.2(8) . . ? N4 C13 C14 115.8(6) . . ? C15 C14 C13 118.3(6) . . ? C15 C14 Ir1 127.8(5) . . ? C13 C14 Ir1 113.7(5) . . ? C16 C15 C14 118.7(7) . . ? C16 C15 H15A 120.7 . . ? C14 C15 H15A 120.7 . . ? F3 C16 C17 118.3(7) . . ? F3 C16 C15 117.9(8) . . ? C17 C16 C15 123.8(8) . . ? C16 C17 C18 117.0(7) . . ? C16 C17 H17A 121.5 . . ? C18 C17 H17A 121.5 . . ? F4 C18 C17 118.7(7) . . ? F4 C18 C13 119.3(9) . . ? C17 C18 C13 122.0(8) . . ? C19 N5 N6 107.1(5) . . ? C19 N5 Ir2 137.3(5) . . ? N6 N5 Ir2 115.1(4) . . ? C21 N6 N5 110.2(6) . . ? C21 N6 C22 134.3(6) . . ? N5 N6 C22 115.2(5) . . ? N5 C19 C20 108.4(6) . . ? N5 C19 H19A 125.8 . . ? C20 C19 H19A 125.8 . . ? C21 C20 C19 107.3(6) . . ? C21 C20 H20A 126.3 . . ? C19 C20 H20A 126.3 . . ? N6 C21 C20 106.9(7) . . ? N6 C21 H21A 126.6 . . ? C20 C21 H21A 126.6 . . ? C27 C22 N6 124.3(6) . . ? C27 C22 C23 120.4(6) . . ? N6 C22 C23 115.3(5) . . ? C24 C23 C22 117.5(6) . . ? C24 C23 Ir2 129.0(5) . . ? C22 C23 Ir2 113.6(4) . . ? C23 C24 C25 119.7(6) . . ? C23 C24 H24A 120.2 . . ? C25 C24 H24A 120.2 . . ? F5 C25 C26 118.4(6) . . ? F5 C25 C24 118.1(6) . . ? C26 C25 C24 123.5(7) . . ? C27 C26 C25 116.8(6) . . ? C27 C26 H26A 121.6 . . ? C25 C26 H26A 121.6 . . ? C28 N7 N8 106.9(5) . . ? C28 N7 Ir2 138.1(4) . . ? N8 N7 Ir2 114.9(4) . . ? C30 N8 N7 109.3(5) . . ? C30 N8 C31 135.5(6) . . ? N7 N8 C31 115.1(5) . . ? F6 C27 C26 118.4(6) . . ? F6 C27 C22 119.4(7) . . ? C26 C27 C22 122.1(6) . . ? N7 C28 C29 110.5(6) . . ? N7 C28 H28A 124.8 . . ? C29 C28 H28A 124.8 . . ? C30 C29 C28 105.1(6) . . ? C30 C29 H29A 127.5 . . ? C28 C29 H29A 127.5 . . ? N8 C30 C29 108.1(6) . . ? N8 C30 H30A 125.9 . . ? C29 C30 H30A 125.9 . . ? C36 C31 C32 121.3(6) . . ? C36 C31 N8 123.4(6) . . ? C32 C31 N8 115.2(5) . . ? C33 C32 C31 117.1(5) . . ? C33 C32 Ir2 128.9(4) . . ? C31 C32 Ir2 113.9(4) . . ? C34 C33 C32 120.0(6) . . ? C34 C33 H33A 120.0 . . ? C32 C33 H33A 120.0 . . ? F7 C34 C33 118.6(6) . . ? F7 C34 C35 117.0(5) . . ? C33 C34 C35 124.4(6) . . ? C34 C35 C36 115.8(6) . . ? C34 C35 H35A 122.1 . . ? C36 C35 H35A 122.1 . . ? F8 C36 C35 118.3(6) . . ? F8 C36 C31 120.2(6) . . ? C35 C36 C31 121.5(6) . . ? Cl11 C100 Cl10 112.8(5) . . ? Cl11 C100 H10B 109.0 . . ? Cl10 C100 H10B 109.0 . . ? Cl11 C100 H10C 109.0 . . ? Cl10 C100 H10C 109.0 . . ? H10B C100 H10C 107.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.250 _refine_diff_density_min -2.273 _refine_diff_density_rms 0.208 data_gs52_2 _database_code_depnum_ccdc_archive 'CCDC 890058' #TrackingRef 'GS52_mono.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H42 F4 Ir N6, F6 P, C H2 Cl2' _chemical_formula_sum 'C49 H44 Cl2 F10 Ir N6 P' _chemical_formula_weight 1200.99 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 '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)/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.8613(17) _cell_length_b 10.0629(5) _cell_length_c 25.126(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.381(6) _cell_angle_gamma 90.00 _cell_volume 4804.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 20067 _cell_measurement_theta_min 4.28 _cell_measurement_theta_max 58.58 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 _exptl_absorpt_coefficient_mu 3.005 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7532 _exptl_absorpt_correction_T_max 0.7950 _exptl_absorpt_process_details '(Blessing 1951)' _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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33704 _diffrn_reflns_av_R_equivalents 0.2023 _diffrn_reflns_av_sigmaI/netI 0.1229 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.05 _reflns_number_total 8485 _reflns_number_gt 6560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _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^)+(0.1148P)^2^+28.5425P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8485 _refine_ls_number_parameters 628 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1085 _refine_ls_R_factor_gt 0.0876 _refine_ls_wR_factor_ref 0.2294 _refine_ls_wR_factor_gt 0.2121 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.70267(2) 0.79902(5) 0.391306(18) 0.03892(19) Uani 1 1 d . . . N1 N 0.7786(5) 0.8733(10) 0.3571(4) 0.040(2) Uani 1 1 d . . . N2 N 0.8036(5) 0.7925(11) 0.4673(4) 0.042(2) Uani 1 1 d . . . C1 C 0.6842(7) 1.0996(14) 0.2927(6) 0.054(3) Uani 1 1 d . . . H1A H 0.7135 1.1232 0.3318 0.065 Uiso 1 1 calc R . . C2 C 0.6265(8) 1.1774(13) 0.2608(7) 0.059(3) Uani 1 1 d . . . H2A H 0.6163 1.2539 0.2780 0.071 Uiso 1 1 calc R . . C3 C 0.5830(7) 1.1433(14) 0.2028(7) 0.057(3) Uani 1 1 d . . . H3A H 0.5424 1.1948 0.1808 0.068 Uiso 1 1 calc R . . C4 C 0.5999(7) 1.0352(15) 0.1787(6) 0.056(3) Uani 1 1 d . . . H4A H 0.5715 1.0135 0.1391 0.068 Uiso 1 1 calc R . . C5 C 0.6586(7) 0.9541(14) 0.2111(5) 0.051(3) Uani 1 1 d . . . H5A H 0.6695 0.8781 0.1939 0.062 Uiso 1 1 calc R . . C6 C 0.6999(6) 0.9891(12) 0.2687(5) 0.042(3) Uani 1 1 d . . . C7 C 0.7639(6) 0.9099(14) 0.3031(5) 0.049(3) Uani 1 1 d . . . C8 C 0.8090(6) 0.8823(15) 0.2761(5) 0.052(3) Uani 1 1 d . . . H8A H 0.7972 0.9110 0.2372 0.063 Uiso 1 1 calc R . . C9 C 0.8708(6) 0.8132(19) 0.3059(5) 0.063(4) Uani 1 1 d . . . C10 C 0.8881(7) 0.7842(19) 0.3661(6) 0.064(4) Uani 1 1 d . . . H10A H 0.9313 0.7421 0.3897 0.077 Uiso 1 1 calc R . . C11 C 0.8414(6) 0.8183(13) 0.3885(5) 0.044(3) Uani 1 1 d . . . C12 C 0.8591(6) 0.7917(14) 0.4519(6) 0.049(3) Uani 1 1 d . . . C13 C 0.9270(6) 0.7763(13) 0.4914(5) 0.044(3) Uani 1 1 d . . . H13A H 0.9637 0.7751 0.4783 0.053 Uiso 1 1 calc R . . C14 C 0.9436(6) 0.7621(16) 0.5509(5) 0.051(3) Uani 1 1 d . . . C15 C 0.8866(7) 0.7648(16) 0.5661(5) 0.053(3) Uani 1 1 d . . . H15A H 0.8947 0.7575 0.6060 0.064 Uiso 1 1 calc R . . C16 C 0.8182(6) 0.7778(14) 0.5241(6) 0.048(3) Uani 1 1 d . . . C17 C 0.7611(6) 0.7800(14) 0.5457(5) 0.046(3) Uani 1 1 d . . . C18 C 0.7356(6) 0.6622(15) 0.5563(5) 0.047(3) Uani 1 1 d . . . H18A H 0.7504 0.5798 0.5466 0.057 Uiso 1 1 calc R . . C19 C 0.6873(6) 0.6660(15) 0.5817(6) 0.052(3) Uani 1 1 d . . . H19A H 0.6701 0.5849 0.5902 0.062 Uiso 1 1 calc R . . C20 C 0.6648(7) 0.7814(16) 0.5945(6) 0.057(3) Uani 1 1 d . . . H20A H 0.6300 0.7816 0.6098 0.069 Uiso 1 1 calc R . . C21 C 0.6919(7) 0.8993(18) 0.5855(6) 0.064(4) Uani 1 1 d . . . H21A H 0.6775 0.9809 0.5962 0.076 Uiso 1 1 calc R . . C22 C 0.7401(7) 0.8994(15) 0.5609(6) 0.054(3) Uani 1 1 d . . . H22A H 0.7588 0.9809 0.5545 0.064 Uiso 1 1 calc R . . C23 C 0.9189(9) 0.767(3) 0.2762(7) 0.098(8) Uani 1 1 d . . . C24 C 0.8823(15) 0.778(4) 0.2141(11) 0.155(11) Uani 1 1 d U . . H24A H 0.8777 0.8724 0.2030 0.232 Uiso 1 1 calc R . . H24B H 0.8353 0.7388 0.2015 0.232 Uiso 1 1 calc R . . H24C H 0.9086 0.7316 0.1954 0.232 Uiso 1 1 calc R . . C25 C 0.9837(11) 0.854(3) 0.3009(10) 0.107(8) Uani 1 1 d . . . H25A H 1.0174 0.8248 0.2852 0.161 Uiso 1 1 calc R . . H25B H 1.0054 0.8456 0.3436 0.161 Uiso 1 1 calc R . . H25C H 0.9706 0.9463 0.2900 0.161 Uiso 1 1 calc R . . C26 C 0.9460(13) 0.623(3) 0.2971(12) 0.137(11) Uani 1 1 d . . . H26A H 0.9631 0.5831 0.2700 0.205 Uiso 1 1 calc R . . H26B H 0.9074 0.5696 0.2983 0.205 Uiso 1 1 calc R . . H26C H 0.9844 0.6273 0.3363 0.205 Uiso 1 1 calc R . . C27 C 1.0192(7) 0.741(2) 0.5939(6) 0.068(5) Uani 1 1 d . . . C28 C 1.0634(8) 0.857(2) 0.5900(7) 0.080(5) Uani 1 1 d . . . H28A H 1.1102 0.8529 0.6223 0.120 Uiso 1 1 calc R . . H28B H 1.0404 0.9408 0.5924 0.120 Uiso 1 1 calc R . . H28C H 1.0680 0.8538 0.5527 0.120 Uiso 1 1 calc R . . C29 C 1.0442(8) 0.613(2) 0.5773(7) 0.083(6) Uani 1 1 d . . . H29A H 1.0410 0.6198 0.5374 0.124 Uiso 1 1 calc R . . H29B H 1.0146 0.5391 0.5795 0.124 Uiso 1 1 calc R . . H29C H 1.0932 0.5962 0.6044 0.124 Uiso 1 1 calc R . . C30 C 1.0249(7) 0.729(3) 0.6566(6) 0.094(8) Uani 1 1 d . . . H30A H 1.0668 0.6772 0.6802 0.142 Uiso 1 1 calc R . . H30B H 0.9829 0.6841 0.6561 0.142 Uiso 1 1 calc R . . H30C H 1.0284 0.8178 0.6735 0.142 Uiso 1 1 calc R . . N3 N 0.7214(5) 0.6240(10) 0.3603(4) 0.041(2) Uani 1 1 d . . . N4 N 0.6790(5) 0.6019(10) 0.3024(4) 0.043(2) Uani 1 1 d . . . F1 F 0.4562(4) 0.9456(8) 0.2113(3) 0.0530(17) Uani 1 1 d . . . F2 F 0.5749(4) 0.5707(8) 0.1873(3) 0.0593(19) Uani 1 1 d . . . C31 C 0.7673(6) 0.5264(13) 0.3789(6) 0.047(3) Uani 1 1 d . . . H31A H 0.8027 0.5174 0.4175 0.056 Uiso 1 1 calc R . . C32 C 0.7557(6) 0.4394(16) 0.3337(6) 0.058(3) Uani 1 1 d . . . H32A H 0.7817 0.3610 0.3351 0.069 Uiso 1 1 calc R . . C33 C 0.6990(6) 0.4878(12) 0.2860(6) 0.047(3) Uani 1 1 d . . . H33A H 0.6780 0.4479 0.2485 0.056 Uiso 1 1 calc R . . C34 C 0.6221(6) 0.6870(12) 0.2764(5) 0.042(3) Uani 1 1 d . . . C35 C 0.6204(6) 0.7940(13) 0.3126(5) 0.044(3) Uani 1 1 d . . . C36 C 0.5608(6) 0.8776(11) 0.2888(5) 0.039(2) Uani 1 1 d . . . H36A H 0.5552 0.9477 0.3118 0.047 Uiso 1 1 calc R . . C37 C 0.5123(6) 0.8596(13) 0.2345(6) 0.047(3) Uani 1 1 d . . . C38 C 0.5148(7) 0.7583(14) 0.1978(6) 0.049(3) Uani 1 1 d . . . H38A H 0.4803 0.7491 0.1588 0.059 Uiso 1 1 calc R . . C39 C 0.5709(6) 0.6719(13) 0.2219(5) 0.045(3) Uani 1 1 d . . . N5 N 0.6737(5) 0.9650(11) 0.4204(4) 0.044(2) Uani 1 1 d . . . N6 N 0.6176(5) 0.9462(11) 0.4353(4) 0.044(2) Uani 1 1 d . . . F3 F 0.5508(4) 0.4262(7) 0.4436(3) 0.0566(18) Uani 1 1 d . . . F4 F 0.5098(4) 0.8712(8) 0.4698(4) 0.0566(19) Uani 1 1 d . . . C40 C 0.6920(6) 1.0927(13) 0.4310(5) 0.048(3) Uani 1 1 d . . . H40A H 0.7293 1.1336 0.4247 0.057 Uiso 1 1 calc R . . C41 C 0.6489(7) 1.1572(14) 0.4524(6) 0.054(3) Uani 1 1 d . . . H41A H 0.6517 1.2478 0.4637 0.064 Uiso 1 1 calc R . . C42 C 0.6024(7) 1.0664(13) 0.4542(6) 0.049(3) Uani 1 1 d . . . H42A H 0.5655 1.0821 0.4663 0.059 Uiso 1 1 calc R . . C43 C 0.5965(6) 0.8187(12) 0.4363(5) 0.043(3) Uani 1 1 d . . . C44 C 0.6328(6) 0.7230(12) 0.4205(5) 0.042(3) Uani 1 1 d . . . C45 C 0.6169(6) 0.5845(13) 0.4226(5) 0.044(3) Uani 1 1 d . . . H45A H 0.6404 0.5160 0.4116 0.052 Uiso 1 1 calc R . . C46 C 0.5660(7) 0.5592(14) 0.4413(6) 0.054(3) Uani 1 1 d . . . C47 C 0.5280(6) 0.6463(14) 0.4582(6) 0.050(3) Uani 1 1 d . . . H47A H 0.4936 0.6193 0.4716 0.060 Uiso 1 1 calc R . . C48 C 0.5445(6) 0.7780(15) 0.4540(5) 0.049(3) Uani 1 1 d . . . P1 P 0.85619(18) 0.3202(4) 0.53395(17) 0.0570(9) Uani 1 1 d . . . F10 F 0.7773(4) 0.3605(11) 0.5181(4) 0.079(3) Uani 1 1 d . . . F11 F 0.8710(5) 0.4623(10) 0.5139(4) 0.080(3) Uani 1 1 d . . . F12 F 0.8780(5) 0.3726(11) 0.5987(4) 0.078(3) Uani 1 1 d . . . F13 F 0.8414(6) 0.1779(11) 0.5523(6) 0.092(3) Uani 1 1 d . . . F14 F 0.8339(4) 0.2685(9) 0.4685(4) 0.065(2) Uani 1 1 d . . . F15 F 0.9356(4) 0.2790(11) 0.5498(4) 0.077(3) Uani 1 1 d . . . C100 C 0.7576(13) 0.219(3) 0.1370(9) 0.117(9) Uani 1 1 d . . . H10B H 0.7733 0.1260 0.1376 0.140 Uiso 1 1 calc R . . H10C H 0.7806 0.2736 0.1170 0.140 Uiso 1 1 calc R . . Cl1 Cl 0.6670(3) 0.2265(6) 0.0973(3) 0.1047(17) Uani 1 1 d . . . Cl2 Cl 0.7840(5) 0.2738(13) 0.2071(3) 0.173(4) 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 Ir1 0.0370(3) 0.0487(3) 0.0358(3) -0.0016(2) 0.01982(19) 0.0000(2) N1 0.043(5) 0.044(6) 0.035(5) -0.005(4) 0.018(4) -0.005(4) N2 0.044(5) 0.058(6) 0.032(5) 0.002(4) 0.023(4) 0.003(5) C1 0.050(7) 0.061(8) 0.062(8) -0.012(7) 0.035(6) -0.003(6) C2 0.071(9) 0.044(8) 0.072(9) 0.019(7) 0.041(8) 0.009(6) C3 0.059(7) 0.050(7) 0.071(9) 0.019(7) 0.036(7) 0.007(6) C4 0.058(7) 0.072(9) 0.044(7) 0.011(7) 0.025(6) 0.000(7) C5 0.064(7) 0.060(8) 0.044(6) 0.005(6) 0.037(6) 0.007(6) C6 0.043(6) 0.043(6) 0.049(6) 0.007(5) 0.028(5) -0.005(5) C7 0.045(6) 0.067(8) 0.043(6) 0.002(6) 0.027(5) 0.001(6) C8 0.055(7) 0.068(9) 0.040(6) -0.008(6) 0.026(6) -0.009(6) C9 0.040(6) 0.124(14) 0.031(6) 0.005(7) 0.019(5) 0.010(7) C10 0.040(6) 0.115(13) 0.038(7) 0.012(8) 0.017(5) 0.013(7) C11 0.040(6) 0.059(8) 0.040(6) -0.005(6) 0.022(5) -0.001(5) C12 0.044(6) 0.061(8) 0.047(7) -0.014(6) 0.023(5) -0.006(6) C13 0.040(6) 0.063(8) 0.036(6) -0.001(5) 0.021(5) 0.000(5) C14 0.043(6) 0.079(9) 0.036(6) -0.010(6) 0.021(5) -0.009(6) C15 0.048(7) 0.079(9) 0.034(6) -0.007(6) 0.019(5) 0.003(6) C16 0.041(6) 0.060(8) 0.045(7) 0.000(6) 0.019(5) -0.006(5) C17 0.037(6) 0.068(8) 0.036(6) 0.000(6) 0.019(5) 0.006(5) C18 0.049(6) 0.068(8) 0.025(5) 0.006(5) 0.016(5) 0.000(6) C19 0.046(6) 0.065(8) 0.049(7) 0.009(6) 0.025(6) 0.005(6) C20 0.046(7) 0.080(10) 0.058(8) 0.007(7) 0.034(6) 0.010(7) C21 0.066(8) 0.086(11) 0.055(8) 0.004(8) 0.041(7) 0.015(8) C22 0.052(7) 0.065(8) 0.050(7) 0.003(7) 0.026(6) 0.006(6) C23 0.052(8) 0.20(2) 0.053(9) -0.008(12) 0.029(7) 0.028(12) C24 0.135(17) 0.27(3) 0.084(14) -0.006(16) 0.072(13) 0.052(18) C25 0.095(13) 0.16(2) 0.099(14) 0.043(15) 0.072(12) 0.021(14) C26 0.112(17) 0.19(3) 0.14(2) -0.04(2) 0.086(16) 0.042(19) C27 0.044(7) 0.132(15) 0.034(7) -0.001(8) 0.021(6) 0.009(8) C28 0.053(8) 0.120(14) 0.071(10) -0.044(10) 0.031(7) -0.031(9) C29 0.049(7) 0.140(17) 0.055(8) 0.014(10) 0.017(7) 0.011(9) C30 0.040(7) 0.21(2) 0.025(6) 0.010(9) 0.009(5) 0.011(10) N3 0.040(5) 0.056(6) 0.036(5) -0.011(4) 0.025(4) 0.010(4) N4 0.043(5) 0.049(6) 0.045(5) 0.000(5) 0.025(4) 0.005(4) F1 0.049(4) 0.054(4) 0.051(4) 0.003(3) 0.016(3) 0.006(3) F2 0.068(4) 0.060(5) 0.049(4) -0.014(4) 0.023(4) 0.004(4) C31 0.044(6) 0.049(7) 0.056(7) 0.000(6) 0.029(6) 0.008(5) C32 0.044(6) 0.067(9) 0.062(8) -0.006(7) 0.023(6) 0.002(6) C33 0.042(6) 0.045(7) 0.052(7) -0.017(6) 0.017(5) 0.002(5) C34 0.038(5) 0.052(7) 0.042(6) 0.008(5) 0.023(5) -0.003(5) C35 0.051(6) 0.052(7) 0.044(6) 0.007(5) 0.034(5) 0.005(5) C36 0.051(6) 0.035(6) 0.040(6) 0.005(5) 0.027(5) 0.007(5) C37 0.039(6) 0.045(7) 0.059(8) 0.001(6) 0.022(5) 0.002(5) C38 0.049(7) 0.051(7) 0.042(6) 0.001(6) 0.014(5) -0.004(5) C39 0.054(7) 0.051(7) 0.036(6) -0.003(5) 0.024(5) -0.003(5) N5 0.037(4) 0.065(7) 0.037(5) -0.010(5) 0.023(4) -0.010(4) N6 0.043(5) 0.055(6) 0.042(5) 0.005(5) 0.027(4) -0.005(4) F3 0.062(4) 0.050(4) 0.068(5) 0.008(4) 0.037(4) -0.007(3) F4 0.055(4) 0.061(5) 0.073(5) -0.011(4) 0.046(4) -0.004(3) C40 0.051(6) 0.046(7) 0.051(7) -0.007(6) 0.026(6) -0.008(6) C41 0.068(8) 0.045(7) 0.058(8) -0.011(6) 0.037(7) 0.006(6) C42 0.053(7) 0.045(7) 0.060(7) -0.003(6) 0.033(6) 0.010(5) C43 0.045(6) 0.048(7) 0.042(6) 0.003(5) 0.025(5) 0.004(5) C44 0.050(6) 0.043(7) 0.032(5) -0.007(5) 0.018(5) -0.016(5) C45 0.042(6) 0.048(7) 0.041(6) -0.003(5) 0.018(5) -0.011(5) C46 0.058(7) 0.053(7) 0.051(7) 0.000(6) 0.022(6) -0.019(6) C47 0.049(7) 0.058(8) 0.052(7) -0.001(6) 0.029(6) -0.012(6) C48 0.034(5) 0.075(9) 0.041(6) 0.004(6) 0.019(5) 0.006(6) P1 0.0467(17) 0.069(2) 0.060(2) 0.0008(18) 0.0266(16) -0.0055(16) F10 0.054(4) 0.093(7) 0.088(6) -0.015(6) 0.027(4) 0.006(5) F11 0.081(6) 0.080(6) 0.074(6) 0.012(5) 0.025(5) -0.020(5) F12 0.074(5) 0.108(8) 0.058(5) -0.011(5) 0.034(4) -0.010(5) F13 0.087(6) 0.082(7) 0.117(9) 0.028(6) 0.053(6) 0.000(5) F14 0.058(4) 0.077(6) 0.062(5) -0.011(4) 0.027(4) -0.004(4) F15 0.046(4) 0.115(8) 0.070(6) 0.009(5) 0.025(4) 0.008(4) C100 0.110(16) 0.18(3) 0.065(12) -0.018(14) 0.037(11) 0.026(16) Cl1 0.097(3) 0.105(4) 0.111(4) 0.026(3) 0.041(3) -0.012(3) Cl2 0.150(6) 0.280(13) 0.087(4) -0.046(6) 0.045(4) -0.009(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 N5 2.014(10) . ? Ir1 C35 2.015(13) . ? Ir1 N3 2.029(9) . ? Ir1 C44 2.034(12) . ? Ir1 N2 2.183(10) . ? Ir1 N1 2.221(9) . ? N1 C7 1.314(15) . ? N1 C11 1.339(15) . ? N2 C16 1.339(16) . ? N2 C12 1.367(15) . ? C1 C6 1.366(18) . ? C1 C2 1.382(19) . ? C1 H1A 0.9500 . ? C2 C3 1.40(2) . ? C2 H2A 0.9500 . ? C3 C4 1.36(2) . ? C3 H3A 0.9500 . ? C4 C5 1.417(19) . ? C4 H4A 0.9500 . ? C5 C6 1.390(18) . ? C5 H5A 0.9500 . ? C6 C7 1.488(17) . ? C7 C8 1.396(17) . ? C8 C9 1.381(19) . ? C8 H8A 0.9500 . ? C9 C10 1.433(18) . ? C9 C23 1.547(19) . ? C10 C11 1.356(18) . ? C10 H10A 0.9500 . ? C11 C12 1.501(18) . ? C12 C13 1.362(17) . ? C13 C14 1.396(17) . ? C13 H13A 0.9500 . ? C14 C15 1.390(18) . ? C14 C27 1.515(18) . ? C15 C16 1.387(17) . ? C15 H15A 0.9500 . ? C16 C17 1.498(16) . ? C17 C18 1.369(19) . ? C17 C22 1.386(19) . ? C18 C19 1.400(17) . ? C18 H18A 0.9500 . ? C19 C20 1.34(2) . ? C19 H19A 0.9500 . ? C20 C21 1.37(2) . ? C20 H20A 0.9500 . ? C21 C22 1.378(18) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 C24 1.43(3) . ? C23 C25 1.51(3) . ? C23 C26 1.56(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C29 1.51(3) . ? C27 C28 1.52(3) . ? C27 C30 1.536(18) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? N3 C31 1.315(15) . ? N3 N4 1.372(13) . ? N4 C33 1.343(15) . ? N4 C34 1.389(15) . ? F1 C37 1.376(14) . ? F2 C39 1.364(14) . ? C31 C32 1.375(19) . ? C31 H31A 0.9500 . ? C32 C33 1.379(18) . ? C32 H32A 0.9500 . ? C33 H33A 0.9500 . ? C34 C39 1.353(17) . ? C34 C35 1.418(17) . ? C35 C36 1.413(16) . ? C36 C37 1.334(17) . ? C36 H36A 0.9500 . ? C37 C38 1.389(19) . ? C38 C39 1.382(19) . ? C38 H38A 0.9500 . ? N5 C40 1.335(17) . ? N5 N6 1.381(12) . ? N6 C43 1.360(16) . ? N6 C42 1.383(16) . ? F3 C46 1.382(16) . ? F4 C48 1.341(15) . ? C40 C41 1.384(17) . ? C40 H40A 0.9500 . ? C41 C42 1.348(19) . ? C41 H41A 0.9500 . ? C42 H42A 0.9500 . ? C43 C44 1.378(17) . ? C43 C48 1.394(17) . ? C44 C45 1.439(17) . ? C45 C46 1.350(17) . ? C45 H45A 0.9500 . ? C46 C47 1.36(2) . ? C47 C48 1.38(2) . ? C47 H47A 0.9500 . ? P1 F13 1.574(11) . ? P1 F10 1.578(9) . ? P1 F12 1.588(9) . ? P1 F11 1.589(10) . ? P1 F15 1.591(9) . ? P1 F14 1.600(9) . ? C100 Cl2 1.71(2) . ? C100 Cl1 1.74(2) . ? C100 H10B 0.9900 . ? C100 H10C 0.9900 . ? 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 N5 Ir1 C35 96.7(4) . . ? N5 Ir1 N3 173.9(4) . . ? C35 Ir1 N3 79.8(4) . . ? N5 Ir1 C44 79.2(4) . . ? C35 Ir1 C44 84.1(4) . . ? N3 Ir1 C44 95.4(4) . . ? N5 Ir1 N2 91.8(4) . . ? C35 Ir1 N2 169.0(4) . . ? N3 Ir1 N2 92.4(4) . . ? C44 Ir1 N2 104.4(4) . . ? N5 Ir1 N1 103.3(4) . . ? C35 Ir1 N1 94.8(4) . . ? N3 Ir1 N1 82.1(4) . . ? C44 Ir1 N1 177.3(4) . . ? N2 Ir1 N1 76.4(3) . . ? C7 N1 C11 118.6(10) . . ? C7 N1 Ir1 126.5(8) . . ? C11 N1 Ir1 108.2(7) . . ? C16 N2 C12 117.2(10) . . ? C16 N2 Ir1 130.5(8) . . ? C12 N2 Ir1 112.1(7) . . ? C6 C1 C2 121.0(13) . . ? C6 C1 H1A 119.5 . . ? C2 C1 H1A 119.5 . . ? C1 C2 C3 119.9(14) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C4 C3 C2 118.8(13) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C3 C4 C5 121.8(13) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C6 C5 C4 118.0(13) . . ? C6 C5 H5A 121.0 . . ? C4 C5 H5A 121.0 . . ? C1 C6 C5 120.5(12) . . ? C1 C6 C7 120.0(12) . . ? C5 C6 C7 119.4(11) . . ? N1 C7 C8 121.9(11) . . ? N1 C7 C6 121.4(10) . . ? C8 C7 C6 116.6(11) . . ? C9 C8 C7 120.2(12) . . ? C9 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? C8 C9 C10 116.5(12) . . ? C8 C9 C23 122.4(12) . . ? C10 C9 C23 121.1(13) . . ? C11 C10 C9 118.4(12) . . ? C11 C10 H10A 120.8 . . ? C9 C10 H10A 120.8 . . ? N1 C11 C10 123.7(11) . . ? N1 C11 C12 116.9(10) . . ? C10 C11 C12 119.4(11) . . ? C13 C12 N2 122.8(12) . . ? C13 C12 C11 121.4(11) . . ? N2 C12 C11 115.7(10) . . ? C12 C13 C14 121.1(11) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C15 C14 C13 115.4(11) . . ? C15 C14 C27 124.4(11) . . ? C13 C14 C27 120.1(11) . . ? C16 C15 C14 121.5(12) . . ? C16 C15 H15A 119.2 . . ? C14 C15 H15A 119.2 . . ? N2 C16 C15 122.0(11) . . ? N2 C16 C17 121.2(10) . . ? C15 C16 C17 116.7(11) . . ? C18 C17 C22 120.3(11) . . ? C18 C17 C16 119.2(12) . . ? C22 C17 C16 120.1(12) . . ? C17 C18 C19 118.3(13) . . ? C17 C18 H18A 120.8 . . ? C19 C18 H18A 120.8 . . ? C20 C19 C18 121.6(14) . . ? C20 C19 H19A 119.2 . . ? C18 C19 H19A 119.2 . . ? C19 C20 C21 119.9(12) . . ? C19 C20 H20A 120.0 . . ? C21 C20 H20A 120.0 . . ? C20 C21 C22 120.0(15) . . ? C20 C21 H21A 120.0 . . ? C22 C21 H21A 120.0 . . ? C21 C22 C17 119.7(14) . . ? C21 C22 H22A 120.1 . . ? C17 C22 H22A 120.1 . . ? C24 C23 C25 113(2) . . ? C24 C23 C9 110.0(15) . . ? C25 C23 C9 106.2(18) . . ? C24 C23 C26 113(2) . . ? C25 C23 C26 104.8(17) . . ? C9 C23 C26 109.4(18) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C29 C27 C14 107.5(13) . . ? C29 C27 C28 110.8(13) . . ? C14 C27 C28 109.0(15) . . ? C29 C27 C30 109.0(16) . . ? C14 C27 C30 110.9(11) . . ? C28 C27 C30 109.5(15) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C31 N3 N4 108.3(9) . . ? C31 N3 Ir1 137.6(8) . . ? N4 N3 Ir1 113.9(7) . . ? C33 N4 N3 108.4(9) . . ? C33 N4 C34 134.1(11) . . ? N3 N4 C34 116.8(9) . . ? N3 C31 C32 109.1(11) . . ? N3 C31 H31A 125.5 . . ? C32 C31 H31A 125.5 . . ? C31 C32 C33 106.7(12) . . ? C31 C32 H32A 126.6 . . ? C33 C32 H32A 126.6 . . ? N4 C33 C32 107.4(11) . . ? N4 C33 H33A 126.3 . . ? C32 C33 H33A 126.3 . . ? C39 C34 N4 124.8(12) . . ? C39 C34 C35 121.1(11) . . ? N4 C34 C35 114.2(10) . . ? C36 C35 C34 115.5(11) . . ? C36 C35 Ir1 130.2(9) . . ? C34 C35 Ir1 114.3(8) . . ? C37 C36 C35 121.0(11) . . ? C37 C36 H36A 119.5 . . ? C35 C36 H36A 119.5 . . ? C36 C37 F1 120.0(11) . . ? C36 C37 C38 123.9(11) . . ? F1 C37 C38 116.1(11) . . ? C39 C38 C37 115.3(11) . . ? C39 C38 H38A 122.3 . . ? C37 C38 H38A 122.3 . . ? C34 C39 F2 120.0(11) . . ? C34 C39 C38 123.0(12) . . ? F2 C39 C38 117.0(11) . . ? C40 N5 N6 106.4(10) . . ? C40 N5 Ir1 140.1(8) . . ? N6 N5 Ir1 113.5(8) . . ? C43 N6 N5 116.8(10) . . ? C43 N6 C42 134.2(10) . . ? N5 N6 C42 108.3(10) . . ? N5 C40 C41 110.5(11) . . ? N5 C40 H40A 124.7 . . ? C41 C40 H40A 124.7 . . ? C42 C41 C40 106.7(11) . . ? C42 C41 H41A 126.6 . . ? C40 C41 H41A 126.6 . . ? C41 C42 N6 108.0(10) . . ? C41 C42 H42A 126.0 . . ? N6 C42 H42A 126.0 . . ? N6 C43 C44 115.7(10) . . ? N6 C43 C48 125.6(11) . . ? C44 C43 C48 118.6(12) . . ? C43 C44 C45 120.3(11) . . ? C43 C44 Ir1 113.6(8) . . ? C45 C44 Ir1 126.0(9) . . ? C46 C45 C44 114.9(12) . . ? C46 C45 H45A 122.6 . . ? C44 C45 H45A 122.6 . . ? C45 C46 C47 129.0(13) . . ? C45 C46 F3 115.1(13) . . ? C47 C46 F3 115.9(11) . . ? C46 C47 C48 113.5(11) . . ? C46 C47 H47A 123.3 . . ? C48 C47 H47A 123.3 . . ? F4 C48 C47 117.8(10) . . ? F4 C48 C43 118.4(12) . . ? C47 C48 C43 123.7(12) . . ? F13 P1 F10 89.8(6) . . ? F13 P1 F12 90.6(7) . . ? F10 P1 F12 90.1(5) . . ? F13 P1 F11 178.6(7) . . ? F10 P1 F11 90.4(6) . . ? F12 P1 F11 90.8(6) . . ? F13 P1 F15 90.0(6) . . ? F10 P1 F15 179.7(7) . . ? F12 P1 F15 90.1(5) . . ? F11 P1 F15 89.7(6) . . ? F13 P1 F14 89.8(6) . . ? F10 P1 F14 89.6(5) . . ? F12 P1 F14 179.5(7) . . ? F11 P1 F14 88.8(5) . . ? F15 P1 F14 90.2(5) . . ? Cl2 C100 Cl1 113.0(13) . . ? Cl2 C100 H10B 109.0 . . ? Cl1 C100 H10B 109.0 . . ? Cl2 C100 H10C 109.0 . . ? Cl1 C100 H10C 109.0 . . ? H10B C100 H10C 107.8 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 4.087 _refine_diff_density_min -2.755 _refine_diff_density_rms 0.210 data_gs53a _database_code_depnum_ccdc_archive 'CCDC 890059' #TrackingRef 'GS53A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H28 F4 Ir N8, F6 P, C H2 Cl2' _chemical_formula_sum 'C33 H30 Cl2 F10 Ir N8 P' _chemical_formula_weight 1022.74 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5146(9) _cell_length_b 14.3727(12) _cell_length_c 14.4945(14) _cell_angle_alpha 102.341(7) _cell_angle_beta 102.295(8) _cell_angle_gamma 105.066(7) _cell_volume 1792.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14443 _cell_measurement_theta_min 4.62 _cell_measurement_theta_max 61.94 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.895 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 4.010 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3343 _exptl_absorpt_correction_T_max 0.5846 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; Two small peaks of residual electron density remain in the difference map. Q1 4.41 (0.809 from Ir1) and Q2 2.89 (1.016 from Ir1) These peaks are the result of fourier truncation surrounding the heavy atom and therefore remain un-assigned. Unfortunately the ellipsoids associated with the ligand disorder were not well behaved had to be regulated with restraints, as did C100 and C200. This is likely due to these positions being even more disordered than modelled. ; _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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39217 _diffrn_reflns_av_R_equivalents 0.1096 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.35 _reflns_number_total 6484 _reflns_number_gt 6436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _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^)+(0.0577P)^2^+6.2899P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6484 _refine_ls_number_parameters 646 _refine_ls_number_restraints 100 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.180 _refine_ls_shift/su_max 0.006 _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 Ir1 Ir 0.79519(2) 0.733271(14) 0.707844(14) 0.02615(11) Uani 1 1 d . . . N1 N 0.8589(5) 0.6547(3) 0.5918(3) 0.0218(9) Uani 1 1 d . A . N2 N 0.9238(6) 0.8485(4) 0.6612(4) 0.0304(10) Uani 1 1 d . A . C1 C 0.8092(6) 0.5534(4) 0.5540(4) 0.0243(10) Uani 1 1 d . . . H1A H 0.7624 0.5137 0.5906 0.029 Uiso 1 1 calc R A . C2 C 0.8228(6) 0.5055(4) 0.4663(4) 0.0251(11) Uani 1 1 d . A . H2A H 0.7874 0.4342 0.4437 0.030 Uiso 1 1 calc R . . C3 C 0.8896(6) 0.5617(4) 0.4083(4) 0.0251(11) Uani 1 1 d . . . C4 C 0.9471(6) 0.6665(4) 0.4505(4) 0.0247(10) Uani 1 1 d . A . H4A H 0.9997 0.7077 0.4173 0.030 Uiso 1 1 calc R . . C5 C 0.9282(6) 0.7099(4) 0.5390(4) 0.0231(10) Uani 1 1 d . . . C6 C 0.9803(6) 0.8198(4) 0.5859(4) 0.0236(10) Uani 1 1 d . A . C7 C 1.0800(6) 0.8876(4) 0.5571(4) 0.0253(11) Uani 1 1 d . . . H7A H 1.1161 0.8647 0.5031 0.030 Uiso 1 1 calc R A . C8 C 1.1290(6) 0.9910(4) 0.6074(4) 0.0266(11) Uani 1 1 d . A . C9 C 1.0659(8) 1.0183(5) 0.6827(5) 0.0365(14) Uani 1 1 d . . . H9A H 1.0929 1.0871 0.7181 0.044 Uiso 1 1 calc R A . C10 C 0.9663(8) 0.9476(5) 0.7062(5) 0.0408(15) Uani 1 1 d . A . H10A H 0.9240 0.9692 0.7574 0.049 Uiso 1 1 calc R . . N3 N 0.8957(6) 0.5163(4) 0.3187(4) 0.0332(11) Uani 1 1 d . A . C11 C 0.8230(8) 0.4083(5) 0.2761(5) 0.0380(14) Uani 1 1 d . . . H11A H 0.8710 0.3729 0.3174 0.057 Uiso 1 1 calc R A . H11B H 0.8341 0.3882 0.2097 0.057 Uiso 1 1 calc R . . H11C H 0.7149 0.3911 0.2724 0.057 Uiso 1 1 calc R . . C12 C 0.9596(10) 0.5747(6) 0.2585(5) 0.0474(17) Uani 1 1 d . . . H12A H 0.9143 0.6283 0.2554 0.071 Uiso 1 1 calc R A . H12B H 0.9379 0.5308 0.1919 0.071 Uiso 1 1 calc R . . H12C H 1.0697 0.6044 0.2877 0.071 Uiso 1 1 calc R . . N4 N 1.2313(6) 1.0593(4) 0.5836(4) 0.0323(10) Uani 1 1 d . . . C13 C 1.3036(9) 1.0295(5) 0.5090(5) 0.0432(16) Uani 1 1 d . A . H13A H 1.3780 1.0891 0.5050 0.065 Uiso 1 1 calc R . . H13B H 1.2266 0.9972 0.4451 0.065 Uiso 1 1 calc R . . H13C H 1.3551 0.9822 0.5264 0.065 Uiso 1 1 calc R . . C14 C 1.2851(8) 1.1643(5) 0.6411(5) 0.0406(14) Uani 1 1 d . A . H14A H 1.1984 1.1892 0.6410 0.061 Uiso 1 1 calc R . . H14B H 1.3544 1.2039 0.6121 0.061 Uiso 1 1 calc R . . H14C H 1.3388 1.1707 0.7090 0.061 Uiso 1 1 calc R . . N5 N 0.9747(6) 0.7408(4) 0.8131(3) 0.0334(11) Uani 1 1 d . A . N6 N 0.9493(6) 0.6727(4) 0.8665(3) 0.0354(11) Uani 1 1 d . . . C15 C 1.1130(9) 0.8060(5) 0.8614(5) 0.0464(17) Uani 1 1 d . . . H15A H 1.1621 0.8617 0.8417 0.056 Uiso 1 1 calc R A . C16 C 1.1745(10) 0.7806(7) 0.9446(5) 0.055(2) Uani 1 1 d . A . H16A H 1.2713 0.8148 0.9911 0.067 Uiso 1 1 calc R . . C17 C 1.0684(9) 0.6966(6) 0.9463(4) 0.0471(17) Uani 1 1 d . A . H17A H 1.0771 0.6615 0.9948 0.057 Uiso 1 1 calc R . . C18 C 0.8046(7) 0.5985(4) 0.8287(4) 0.0278(11) Uani 1 1 d . A . C19 C 0.7040(7) 0.6134(4) 0.7525(4) 0.0276(11) Uani 1 1 d . A . C20 C 0.5609(7) 0.5410(5) 0.7123(4) 0.0290(11) Uani 1 1 d . . . H20A H 0.4878 0.5482 0.6608 0.035 Uiso 1 1 calc R A . C21 C 0.5266(7) 0.4596(5) 0.7476(4) 0.0306(12) Uani 1 1 d . A . C22 C 0.6251(8) 0.4417(5) 0.8206(5) 0.0350(13) Uani 1 1 d . . . H22A H 0.5984 0.3829 0.8416 0.042 Uiso 1 1 calc R A . C23 C 0.7659(7) 0.5148(5) 0.8617(4) 0.0331(12) Uani 1 1 d . A . F1 F 0.3867(4) 0.3896(3) 0.7069(3) 0.0455(9) Uani 1 1 d . . . F2 F 0.8674(5) 0.5012(4) 0.9335(3) 0.0536(11) Uani 1 1 d . . . N7 N 0.5925(9) 0.7218(6) 0.6018(7) 0.0212(17) Uani 0.662(9) 1 d PU A 1 N8 N 0.5104(11) 0.7770(7) 0.6385(9) 0.0259(19) Uani 0.662(9) 1 d P A 1 C24 C 0.5289(10) 0.6799(8) 0.5085(8) 0.0273(19) Uani 0.662(9) 1 d PU A 1 H24A H 0.5646 0.6374 0.4661 0.033 Uiso 0.662(9) 1 calc PR A 1 C25 C 0.3972(12) 0.7076(10) 0.4797(11) 0.040(3) Uani 0.662(9) 1 d P A 1 H25A H 0.3275 0.6885 0.4161 0.048 Uiso 0.662(9) 1 calc PR A 1 C26 C 0.3946(16) 0.7689(13) 0.5665(14) 0.031(4) Uani 0.662(9) 1 d P A 1 H26A H 0.3197 0.8006 0.5729 0.038 Uiso 0.662(9) 1 calc PR A 1 C27 C 0.5669(14) 0.8277(9) 0.7394(13) 0.026(2) Uani 0.662(9) 1 d PU A 1 C28 C 0.7030(15) 0.8173(8) 0.7902(9) 0.026(2) Uani 0.662(9) 1 d P A 1 C29 C 0.7608(15) 0.8669(8) 0.8900(9) 0.031(2) Uani 0.662(9) 1 d P A 1 H29A H 0.8503 0.8605 0.9282 0.037 Uiso 0.662(9) 1 calc PR A 1 C30 C 0.685(2) 0.9257(11) 0.9322(11) 0.045(4) Uani 0.662(9) 1 d P A 1 C31 C 0.5555(16) 0.9374(11) 0.8859(11) 0.048(4) Uani 0.662(9) 1 d PU A 1 H31A H 0.5066 0.9778 0.9193 0.058 Uiso 0.662(9) 1 calc PR A 1 C32 C 0.4986(14) 0.8878(8) 0.7883(9) 0.042(3) Uani 0.662(9) 1 d P A 1 F3 F 0.7422(10) 0.9743(5) 1.0317(5) 0.059(2) Uani 0.662(9) 1 d P A 1 F4 F 0.3669(8) 0.8971(6) 0.7363(6) 0.061(2) Uani 0.662(9) 1 d P A 1 N7' N 0.6232(17) 0.7442(12) 0.6398(13) 0.021(3) Uani 0.338(9) 1 d PU A 2 N8' N 0.546(2) 0.8023(14) 0.691(2) 0.015(4) Uani 0.338(9) 1 d PU A 2 C24' C 0.533(2) 0.7166(16) 0.5448(17) 0.022(4) Uani 0.338(9) 1 d PU A 2 H24B H 0.5540 0.6762 0.4916 0.027 Uiso 0.338(9) 1 calc PR A 2 C25' C 0.408(4) 0.752(3) 0.531(3) 0.031(7) Uani 0.338(9) 1 d PU A 2 H25B H 0.3328 0.7418 0.4722 0.037 Uiso 0.338(9) 1 calc PR A 2 C26' C 0.423(2) 0.8067(16) 0.627(2) 0.030(4) Uani 0.338(9) 1 d PU A 2 H26B H 0.3560 0.8416 0.6451 0.036 Uiso 0.338(9) 1 calc PR A 2 C27' C 0.619(3) 0.8431(14) 0.792(2) 0.024(4) Uani 0.338(9) 1 d PU A 2 C28' C 0.757(3) 0.8246(13) 0.8295(18) 0.017(4) Uani 0.338(9) 1 d PU A 2 C29' C 0.831(2) 0.8627(14) 0.9283(15) 0.026(4) Uani 0.338(9) 1 d P A 2 H29B H 0.9221 0.8493 0.9537 0.032 Uiso 0.338(9) 1 calc PR A 2 C30' C 0.778(3) 0.9181(17) 0.9889(17) 0.044(5) Uani 0.338(9) 1 d P A 2 C31' C 0.646(3) 0.939(2) 0.957(2) 0.039(6) Uani 0.338(9) 1 d P A 2 H31B H 0.6087 0.9786 1.0018 0.047 Uiso 0.338(9) 1 calc PR A 2 C32' C 0.569(2) 0.9019(17) 0.8578(17) 0.028(5) Uani 0.338(9) 1 d PU A 2 F3' F 0.8504(16) 0.9545(11) 1.0866(9) 0.055(4) Uani 0.338(9) 1 d P A 2 F4' F 0.4383(16) 0.9210(11) 0.8236(11) 0.056(4) Uani 0.338(9) 1 d P A 2 P1 P 0.7431(2) 1.17066(16) 0.75616(13) 0.0485(4) Uani 1 1 d . . . F10 F 0.8533(6) 1.1770(4) 0.6861(4) 0.0665(14) Uani 1 1 d . . . F11 F 0.6336(7) 1.1655(6) 0.8255(4) 0.0867(19) Uani 1 1 d . . . F12 F 0.8385(9) 1.1201(5) 0.8186(5) 0.091(2) Uani 1 1 d . . . F13 F 0.6367(10) 1.0657(6) 0.6854(5) 0.124(4) Uani 1 1 d . . . F14 F 0.8468(7) 1.2773(4) 0.8265(3) 0.0672(14) Uani 1 1 d . . . F15 F 0.6484(9) 1.2238(8) 0.6943(5) 0.112(3) Uani 1 1 d . . . C100 C 1.4437(19) 1.3080(16) 1.0095(17) 0.103(7) Uani 0.630(9) 1 d PDU B 1 H10B H 1.4174 1.2898 1.0673 0.124 Uiso 0.630(9) 1 calc PR B 1 H10C H 1.4806 1.2551 0.9769 0.124 Uiso 0.630(9) 1 calc PR B 1 Cl1 Cl 1.5830(9) 1.4127(6) 1.0497(3) 0.115(3) Uani 0.630(9) 1 d PD B 1 Cl2 Cl 1.2752(13) 1.3040(9) 0.9267(6) 0.131(3) Uani 0.630(9) 1 d PD B 1 C200 C 1.383(2) 1.3338(19) 1.0028(17) 0.070(7) Uani 0.370(9) 1 d PDU B 2 H20B H 1.4264 1.4064 1.0101 0.084 Uiso 0.370(9) 1 calc PR B 2 H20C H 1.3730 1.3258 1.0675 0.084 Uiso 0.370(9) 1 calc PR B 2 Cl3 Cl 1.5000(15) 1.2703(9) 0.9637(10) 0.133(6) Uani 0.370(9) 1 d PD B 2 Cl4 Cl 1.2039(11) 1.2845(13) 0.9151(10) 0.100(4) Uani 0.370(9) 1 d PD B 2 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 0.03153(16) 0.01697(14) 0.04028(15) 0.01164(10) 0.02438(10) 0.01052(10) N1 0.022(2) 0.018(2) 0.028(2) 0.0099(17) 0.0085(17) 0.0078(18) N2 0.036(3) 0.022(2) 0.045(3) 0.015(2) 0.026(2) 0.013(2) C1 0.024(3) 0.020(3) 0.033(3) 0.013(2) 0.011(2) 0.006(2) C2 0.026(3) 0.018(3) 0.033(3) 0.008(2) 0.010(2) 0.009(2) C3 0.024(3) 0.028(3) 0.031(2) 0.012(2) 0.012(2) 0.013(2) C4 0.024(3) 0.025(3) 0.032(3) 0.013(2) 0.013(2) 0.010(2) C5 0.020(2) 0.023(3) 0.033(2) 0.013(2) 0.011(2) 0.012(2) C6 0.023(3) 0.021(3) 0.034(3) 0.013(2) 0.012(2) 0.012(2) C7 0.027(3) 0.022(3) 0.034(3) 0.014(2) 0.014(2) 0.011(2) C8 0.025(3) 0.020(3) 0.040(3) 0.016(2) 0.012(2) 0.009(2) C9 0.045(4) 0.018(3) 0.053(4) 0.012(3) 0.026(3) 0.012(3) C10 0.052(4) 0.018(3) 0.064(4) 0.012(3) 0.040(3) 0.013(3) N3 0.040(3) 0.028(3) 0.036(2) 0.009(2) 0.018(2) 0.012(2) C11 0.039(3) 0.031(3) 0.039(3) 0.001(2) 0.014(3) 0.010(3) C12 0.061(5) 0.044(4) 0.040(3) 0.012(3) 0.029(3) 0.010(3) N4 0.036(3) 0.020(2) 0.046(3) 0.015(2) 0.021(2) 0.007(2) C13 0.052(4) 0.032(4) 0.054(4) 0.018(3) 0.032(3) 0.009(3) C14 0.047(4) 0.022(3) 0.054(4) 0.015(3) 0.023(3) 0.004(3) N5 0.040(3) 0.025(3) 0.028(2) 0.0014(19) 0.016(2) -0.002(2) N6 0.041(3) 0.032(3) 0.028(2) 0.007(2) 0.014(2) 0.002(2) C15 0.051(4) 0.032(4) 0.039(3) -0.001(3) 0.015(3) -0.009(3) C16 0.047(4) 0.056(5) 0.033(3) -0.003(3) -0.002(3) -0.011(4) C17 0.048(4) 0.052(4) 0.026(3) 0.005(3) 0.006(3) 0.000(3) C18 0.032(3) 0.022(3) 0.028(2) 0.004(2) 0.015(2) 0.004(2) C19 0.034(3) 0.023(3) 0.033(3) 0.007(2) 0.021(2) 0.013(2) C20 0.027(3) 0.029(3) 0.039(3) 0.015(2) 0.018(2) 0.011(2) C21 0.026(3) 0.026(3) 0.043(3) 0.012(2) 0.016(2) 0.006(2) C22 0.043(4) 0.027(3) 0.043(3) 0.019(3) 0.021(3) 0.011(3) C23 0.037(3) 0.034(3) 0.031(3) 0.017(2) 0.011(2) 0.011(3) F1 0.032(2) 0.034(2) 0.068(2) 0.0254(18) 0.0132(17) -0.0004(16) F2 0.051(3) 0.061(3) 0.048(2) 0.033(2) 0.0044(19) 0.010(2) N7 0.0203(19) 0.0214(19) 0.0218(19) 0.0067(11) 0.0050(11) 0.0068(11) N8 0.027(4) 0.026(4) 0.030(5) 0.013(4) 0.012(4) 0.009(4) C24 0.028(5) 0.023(5) 0.029(4) 0.013(4) 0.007(3) 0.002(4) C25 0.033(5) 0.040(7) 0.050(7) 0.027(6) 0.011(5) 0.007(5) C26 0.024(6) 0.035(8) 0.038(11) 0.020(9) 0.005(7) 0.010(5) C27 0.026(6) 0.023(5) 0.027(7) 0.006(5) 0.007(6) 0.004(4) C28 0.028(6) 0.025(5) 0.021(5) 0.010(4) 0.008(5) 0.002(5) C29 0.040(7) 0.026(5) 0.029(6) 0.004(5) 0.017(5) 0.013(4) C30 0.062(11) 0.037(7) 0.051(9) 0.012(6) 0.042(8) 0.019(6) C31 0.058(9) 0.040(7) 0.063(8) 0.008(6) 0.050(8) 0.022(6) C32 0.044(6) 0.040(6) 0.067(8) 0.025(5) 0.038(6) 0.028(5) F3 0.088(6) 0.041(4) 0.045(4) -0.009(3) 0.034(4) 0.022(4) F4 0.051(4) 0.072(5) 0.090(6) 0.033(4) 0.037(4) 0.049(4) N7' 0.021(3) 0.021(3) 0.020(3) 0.0063(14) 0.0061(14) 0.0056(14) N8' 0.016(7) 0.013(7) 0.015(8) 0.004(6) 0.000(7) 0.007(5) C24' 0.023(4) 0.022(4) 0.022(4) 0.0067(16) 0.0061(16) 0.0071(17) C25' 0.037(12) 0.037(14) 0.021(14) 0.017(12) 0.007(10) 0.011(9) C26' 0.024(8) 0.027(8) 0.043(10) 0.013(8) 0.007(7) 0.017(7) C27' 0.014(7) 0.021(7) 0.037(9) 0.004(6) 0.009(6) 0.005(6) C28' 0.025(8) 0.011(6) 0.013(8) -0.003(6) 0.005(6) 0.006(6) C29' 0.021(9) 0.031(10) 0.027(9) 0.005(7) 0.008(7) 0.009(7) C30' 0.044(12) 0.034(11) 0.042(11) -0.002(9) 0.013(10) 0.004(9) C31' 0.035(14) 0.038(13) 0.048(19) 0.002(11) 0.023(13) 0.016(10) C32' 0.024(7) 0.029(8) 0.027(8) -0.002(6) 0.011(6) 0.010(6) F3' 0.056(8) 0.055(8) 0.042(6) -0.017(5) 0.012(6) 0.026(7) F4' 0.042(8) 0.060(9) 0.070(9) 0.007(7) 0.015(7) 0.033(7) P1 0.0535(11) 0.0506(11) 0.0397(8) 0.0079(8) 0.0205(8) 0.0121(9) F10 0.073(3) 0.056(3) 0.064(3) 0.002(2) 0.041(3) 0.006(2) F11 0.086(4) 0.112(5) 0.066(3) 0.018(3) 0.050(3) 0.021(4) F12 0.125(6) 0.076(4) 0.109(5) 0.047(4) 0.051(4) 0.061(4) F13 0.128(6) 0.102(6) 0.077(4) -0.026(4) 0.061(4) -0.056(5) F14 0.096(4) 0.049(3) 0.049(2) 0.005(2) 0.027(2) 0.013(3) F15 0.100(5) 0.200(9) 0.075(4) 0.063(5) 0.032(4) 0.085(6) C100 0.095(10) 0.119(11) 0.138(11) 0.061(9) 0.064(8) 0.057(8) Cl1 0.178(7) 0.159(6) 0.067(3) 0.049(3) 0.055(3) 0.120(6) Cl2 0.126(8) 0.177(9) 0.082(4) 0.016(4) 0.024(5) 0.058(8) C200 0.079(14) 0.074(14) 0.093(15) 0.026(11) 0.052(12) 0.057(12) Cl3 0.173(11) 0.135(9) 0.223(13) 0.138(10) 0.155(11) 0.117(9) Cl4 0.050(5) 0.169(11) 0.080(6) 0.064(6) 0.011(4) 0.020(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 Ir1 N7' 1.785(15) . ? Ir1 N5 1.995(6) . ? Ir1 C28 2.009(11) . ? Ir1 C19 2.020(6) . ? Ir1 N1 2.109(4) . ? Ir1 N2 2.115(5) . ? Ir1 C28' 2.12(2) . ? Ir1 N7 2.139(9) . ? N1 C1 1.355(7) . ? N1 C5 1.361(7) . ? N2 C10 1.345(8) . ? N2 C6 1.350(7) . ? C1 C2 1.360(8) . ? C1 H1A 0.9500 . ? C2 C3 1.419(8) . ? C2 H2A 0.9500 . ? C3 N3 1.343(7) . ? C3 C4 1.406(8) . ? C4 C5 1.372(8) . ? C4 H4A 0.9500 . ? C5 C6 1.480(8) . ? C6 C7 1.373(8) . ? C7 C8 1.411(8) . ? C7 H7A 0.9500 . ? C8 N4 1.349(7) . ? C8 C9 1.387(9) . ? C9 C10 1.353(9) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? N3 C12 1.452(8) . ? N3 C11 1.455(8) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N4 C13 1.448(8) . ? N4 C14 1.455(8) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N5 C15 1.336(9) . ? N5 N6 1.376(7) . ? N6 C17 1.346(9) . ? N6 C18 1.414(8) . ? C15 C16 1.389(11) . ? C15 H15A 0.9500 . ? C16 C17 1.367(11) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C23 1.379(8) . ? C18 C19 1.393(8) . ? C19 C20 1.393(9) . ? C20 C21 1.366(9) . ? C20 H20A 0.9500 . ? C21 F1 1.359(7) . ? C21 C22 1.372(9) . ? C22 C23 1.383(9) . ? C22 H22A 0.9500 . ? C23 F2 1.346(7) . ? N7 C24 1.293(15) . ? N7 N8 1.356(12) . ? N8 C26 1.307(19) . ? N8 C27 1.402(16) . ? C24 C25 1.418(15) . ? C24 H24A 0.9500 . ? C25 C26 1.38(2) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 C32 1.377(17) . ? C27 C28 1.407(19) . ? C28 C29 1.384(15) . ? C29 C30 1.38(2) . ? C29 H29A 0.9500 . ? C30 C31 1.34(2) . ? C30 F3 1.379(17) . ? C31 C32 1.36(2) . ? C31 H31A 0.9500 . ? C32 F4 1.373(14) . ? N7' C24' 1.37(2) . ? N7' N8' 1.44(2) . ? N8' C26' 1.35(3) . ? N8' C27' 1.40(3) . ? C24' C25' 1.41(4) . ? C24' H24B 0.9500 . ? C25' C26' 1.40(3) . ? C25' H25B 0.9500 . ? C26' H26B 0.9500 . ? C27' C32' 1.38(4) . ? C27' C28' 1.42(3) . ? C28' C29' 1.37(3) . ? C29' C30' 1.33(3) . ? C29' H29B 0.9500 . ? C30' F3' 1.36(3) . ? C30' C31' 1.38(4) . ? C31' C32' 1.38(4) . ? C31' H31B 0.9500 . ? C32' F4' 1.35(3) . ? P1 F12 1.564(6) . ? P1 F13 1.567(6) . ? P1 F14 1.575(5) . ? P1 F15 1.584(7) . ? P1 F11 1.593(5) . ? P1 F10 1.606(5) . ? C100 Cl1 1.619(16) . ? C100 Cl2 1.766(16) . ? C100 H10B 0.9900 . ? C100 H10C 0.9900 . ? C200 Cl3 1.724(16) . ? C200 Cl4 1.756(18) . ? C200 H20B 0.9900 . ? C200 H20C 0.9900 . ? 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 N7' Ir1 N5 165.2(6) . . ? N7' Ir1 C28 66.3(7) . . ? N5 Ir1 C28 99.0(4) . . ? N7' Ir1 C19 98.4(5) . . ? N5 Ir1 C19 80.0(2) . . ? C28 Ir1 C19 90.7(3) . . ? N7' Ir1 N1 100.0(5) . . ? N5 Ir1 N1 94.72(19) . . ? C28 Ir1 N1 165.3(4) . . ? C19 Ir1 N1 96.87(19) . . ? N7' Ir1 N2 90.4(5) . . ? N5 Ir1 N2 92.8(2) . . ? C28 Ir1 N2 97.7(3) . . ? C19 Ir1 N2 169.7(2) . . ? N1 Ir1 N2 76.20(18) . . ? N7' Ir1 C28' 84.0(8) . . ? N5 Ir1 C28' 81.2(7) . . ? C28 Ir1 C28' 17.8(4) . . ? C19 Ir1 C28' 87.7(5) . . ? N1 Ir1 C28' 173.4(6) . . ? N2 Ir1 C28' 98.6(5) . . ? N7' Ir1 N7 12.3(5) . . ? N5 Ir1 N7 175.7(2) . . ? C28 Ir1 N7 78.4(5) . . ? C19 Ir1 N7 96.6(3) . . ? N1 Ir1 N7 88.2(3) . . ? N2 Ir1 N7 90.8(2) . . ? C28' Ir1 N7 96.1(7) . . ? C1 N1 C5 117.3(5) . . ? C1 N1 Ir1 124.5(4) . . ? C5 N1 Ir1 116.8(4) . . ? C10 N2 C6 117.2(5) . . ? C10 N2 Ir1 125.4(4) . . ? C6 N2 Ir1 117.1(4) . . ? N1 C1 C2 123.4(5) . . ? N1 C1 H1A 118.3 . . ? C2 C1 H1A 118.3 . . ? C1 C2 C3 120.3(5) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? N3 C3 C4 123.0(5) . . ? N3 C3 C2 121.2(5) . . ? C4 C3 C2 115.7(5) . . ? C5 C4 C3 120.8(5) . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.6 . . ? N1 C5 C4 122.4(5) . . ? N1 C5 C6 113.9(5) . . ? C4 C5 C6 123.7(5) . . ? N2 C6 C7 122.2(5) . . ? N2 C6 C5 114.5(5) . . ? C7 C6 C5 123.3(5) . . ? C6 C7 C8 120.3(5) . . ? C6 C7 H7A 119.8 . . ? C8 C7 H7A 119.8 . . ? N4 C8 C9 122.0(5) . . ? N4 C8 C7 121.9(5) . . ? C9 C8 C7 116.1(5) . . ? C10 C9 C8 120.5(6) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? N2 C10 C9 123.7(6) . . ? N2 C10 H10A 118.2 . . ? C9 C10 H10A 118.2 . . ? C3 N3 C12 120.8(5) . . ? C3 N3 C11 120.1(5) . . ? C12 N3 C11 118.7(5) . . ? N3 C11 H11A 109.5 . . ? N3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 N4 C13 121.7(5) . . ? C8 N4 C14 120.0(5) . . ? C13 N4 C14 117.9(5) . . ? N4 C13 H13A 109.5 . . ? N4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 H14A 109.5 . . ? N4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C15 N5 N6 105.4(5) . . ? C15 N5 Ir1 137.3(5) . . ? N6 N5 Ir1 115.9(4) . . ? C17 N6 N5 110.7(6) . . ? C17 N6 C18 135.1(6) . . ? N5 N6 C18 114.2(5) . . ? N5 C15 C16 110.3(6) . . ? N5 C15 H15A 124.9 . . ? C16 C15 H15A 124.9 . . ? C17 C16 C15 106.4(6) . . ? C17 C16 H16A 126.8 . . ? C15 C16 H16A 126.8 . . ? N6 C17 C16 107.2(6) . . ? N6 C17 H17A 126.4 . . ? C16 C17 H17A 126.4 . . ? C23 C18 C19 121.6(6) . . ? C23 C18 N6 123.0(5) . . ? C19 C18 N6 115.4(5) . . ? C18 C19 C20 117.1(5) . . ? C18 C19 Ir1 113.9(4) . . ? C20 C19 Ir1 128.7(4) . . ? C21 C20 C19 119.5(5) . . ? C21 C20 H20A 120.3 . . ? C19 C20 H20A 120.3 . . ? F1 C21 C20 118.5(5) . . ? F1 C21 C22 116.9(5) . . ? C20 C21 C22 124.6(6) . . ? C21 C22 C23 115.7(5) . . ? C21 C22 H22A 122.2 . . ? C23 C22 H22A 122.2 . . ? F2 C23 C18 120.1(6) . . ? F2 C23 C22 118.3(5) . . ? C18 C23 C22 121.6(5) . . ? C24 N7 N8 109.4(10) . . ? C24 N7 Ir1 136.9(7) . . ? N8 N7 Ir1 113.6(8) . . ? C26 N8 N7 108.4(12) . . ? C26 N8 C27 135.9(12) . . ? N7 N8 C27 115.7(10) . . ? N7 C24 C25 108.9(12) . . ? N7 C24 H24A 125.5 . . ? C25 C24 H24A 125.5 . . ? C26 C25 C24 103.3(12) . . ? C26 C25 H25A 128.3 . . ? C24 C25 H25A 128.3 . . ? N8 C26 C25 110.0(14) . . ? N8 C26 H26A 125.0 . . ? C25 C26 H26A 125.0 . . ? C32 C27 N8 123.3(12) . . ? C32 C27 C28 120.1(15) . . ? N8 C27 C28 116.6(11) . . ? C29 C28 C27 117.6(12) . . ? C29 C28 Ir1 126.9(10) . . ? C27 C28 Ir1 115.6(9) . . ? C30 C29 C28 118.1(13) . . ? C30 C29 H29A 121.0 . . ? C28 C29 H29A 121.0 . . ? C31 C30 C29 125.8(16) . . ? C31 C30 F3 116.4(16) . . ? C29 C30 F3 117.8(15) . . ? C30 C31 C32 115.8(14) . . ? C30 C31 H31A 122.1 . . ? C32 C31 H31A 122.1 . . ? C31 C32 F4 118.7(10) . . ? C31 C32 C27 122.7(13) . . ? F4 C32 C27 118.6(12) . . ? C24' N7' N8' 101.3(16) . . ? C24' N7' Ir1 139.8(14) . . ? N8' N7' Ir1 118.8(15) . . ? C26' N8' C27' 136(2) . . ? C26' N8' N7' 111(2) . . ? C27' N8' N7' 113.1(15) . . ? N7' C24' C25' 115(2) . . ? N7' C24' H24B 122.3 . . ? C25' C24' H24B 122.3 . . ? C26' C25' C24' 103(3) . . ? C26' C25' H25B 128.7 . . ? C24' C25' H25B 128.7 . . ? N8' C26' C25' 110(2) . . ? N8' C26' H26B 124.9 . . ? C25' C26' H26B 124.9 . . ? C32' C27' N8' 125(2) . . ? C32' C27' C28' 118(2) . . ? N8' C27' C28' 117.8(19) . . ? C29' C28' C27' 119.5(19) . . ? C29' C28' Ir1 134.3(16) . . ? C27' C28' Ir1 106.2(16) . . ? C30' C29' C28' 121(2) . . ? C30' C29' H29B 119.6 . . ? C28' C29' H29B 119.6 . . ? C29' C30' F3' 121(2) . . ? C29' C30' C31' 123(2) . . ? F3' C30' C31' 117(2) . . ? C30' C31' C32' 118(3) . . ? C30' C31' H31B 121.2 . . ? C32' C31' H31B 121.2 . . ? F4' C32' C31' 119(3) . . ? F4' C32' C27' 119(2) . . ? C31' C32' C27' 122(2) . . ? F12 P1 F13 91.4(5) . . ? F12 P1 F14 89.9(4) . . ? F13 P1 F14 178.5(5) . . ? F12 P1 F15 179.0(5) . . ? F13 P1 F15 89.6(6) . . ? F14 P1 F15 89.0(4) . . ? F12 P1 F11 89.7(4) . . ? F13 P1 F11 89.9(4) . . ? F14 P1 F11 89.6(3) . . ? F15 P1 F11 90.3(4) . . ? F12 P1 F10 90.9(4) . . ? F13 P1 F10 90.5(3) . . ? F14 P1 F10 90.1(3) . . ? F15 P1 F10 89.2(3) . . ? F11 P1 F10 179.4(4) . . ? Cl1 C100 Cl2 117.8(12) . . ? Cl1 C100 H10B 107.9 . . ? Cl2 C100 H10B 107.9 . . ? Cl1 C100 H10C 107.9 . . ? Cl2 C100 H10C 107.9 . . ? H10B C100 H10C 107.2 . . ? Cl3 C200 Cl4 108.6(13) . . ? Cl3 C200 H20B 110.0 . . ? Cl4 C200 H20B 110.0 . . ? Cl3 C200 H20C 110.0 . . ? Cl4 C200 H20C 110.0 . . ? H20B C200 H20C 108.3 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 4.410 _refine_diff_density_min -2.485 _refine_diff_density_rms 0.169 data_ligand _database_code_depnum_ccdc_archive 'CCDC 890060' #TrackingRef 'ligand .cif' _audit_creation_date 10-08-05 _audit_creation_method CRYSTALS_ver_14.09 _oxford_structure_analysis_title 'gs052_123k_0ma in C2/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 19.8624(12) _cell_length_b 6.1354(3) _cell_length_c 19.9421(13) _cell_angle_alpha 90 _cell_angle_beta 106.045(5) _cell_angle_gamma 90 _cell_volume 2335.6(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C30 H32 N2 # Dc = 1.20 Fooo = 904.00 Mu = 0.69 M = 210.30 # Found Formula = C30 H32 N2 # Dc = 1.20 FOOO = 904.00 Mu = 0.69 M = 210.30 _chemical_formula_sum 'C30 H32 N2' _chemical_formula_moiety 'C30 H32 N2' _chemical_compound_source ? _chemical_formula_weight 420.60 _cell_measurement_reflns_used 9828 _cell_measurement_theta_min 3 _cell_measurement_theta_max 39 _cell_measurement_temperature 123 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_max 0.260 _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.069 # Sheldrick geometric approximatio 0.99 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 87729 _reflns_number_total 6278 _diffrn_reflns_av_R_equivalents 0.052 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 6278 # Theoretical number of reflections is about 12540 _diffrn_reflns_theta_min 2.125 _diffrn_reflns_theta_max 37.790 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 37.790 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _reflns_limit_h_min -34 _reflns_limit_h_max 32 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 34 _oxford_diffrn_Wilson_B_factor 1.07 _oxford_diffrn_Wilson_scale 1080.94 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.53 _refine_diff_density_max 0.62 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 5623 _refine_ls_number_restraints 0 _refine_ls_number_parameters 145 _oxford_refine_ls_R_factor_ref 0.0500 _refine_ls_wR_factor_ref 0.0537 _refine_ls_goodness_of_fit_ref 1.0471 _refine_ls_shift/su_max 0.0009444 _refine_ls_shift/su_mean 0.0000989 # The values computed from all data _oxford_reflns_number_all 6270 _refine_ls_R_factor_all 0.0560 _refine_ls_wR_factor_all 0.0703 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5840 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_gt 0.0552 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.273 0.296 0.920E-01 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.23700(3) 0.34592(9) 0.47698(3) 0.0137 1.0000 Uani . . . . . . C2 C 0.17390(3) 0.44676(9) 0.47646(3) 0.0149 1.0000 Uani . . . . . . C3 C 0.15002(3) 0.62423(9) 0.43223(3) 0.0134 1.0000 Uani . . . . . . C4 C 0.19273(3) 0.69360(9) 0.39150(3) 0.0147 1.0000 Uani . . . . . . C5 C 0.25541(3) 0.58395(9) 0.39488(3) 0.0135 1.0000 Uani . . . . . . C6 C 0.29993(3) 0.64745(9) 0.34936(3) 0.0140 1.0000 Uani . . . . . . C7 C 0.29828(3) 0.85757(10) 0.32168(3) 0.0173 1.0000 Uani . . . . . . C8 C 0.33879(3) 0.90866(10) 0.27692(3) 0.0195 1.0000 Uani . . . . . . C9 C 0.38153(3) 0.75168(11) 0.25939(3) 0.0206 1.0000 Uani . . . . . . C10 C 0.38427(3) 0.54328(11) 0.28764(3) 0.0197 1.0000 Uani . . . . . . C11 C 0.34402(3) 0.49153(10) 0.33235(3) 0.0169 1.0000 Uani . . . . . . C12 C 0.07782(3) 0.72420(9) 0.42502(3) 0.0141 1.0000 Uani . . . . . . C13 C 0.06178(4) 0.73933(18) 0.49564(4) 0.0337 1.0000 Uani . . . . . . C14 C 0.02307(4) 0.57800(13) 0.37621(5) 0.0290 1.0000 Uani . . . . . . C15 C 0.07154(4) 0.95425(11) 0.39464(5) 0.0291 1.0000 Uani . . . . . . N1 N 0.27714(3) 0.41166(8) 0.43667(3) 0.0142 1.0000 Uani . . . . . . H21 H 0.1473 0.3932 0.5088 0.0190 1.0000 Uiso R . . . . . H41 H 0.1794 0.8116 0.3595 0.0179 1.0000 Uiso R . . . . . H71 H 0.2699 0.9655 0.3361 0.0220 1.0000 Uiso R . . . . . H81 H 0.3380 1.0501 0.2560 0.0253 1.0000 Uiso R . . . . . H91 H 0.4090 0.7862 0.2269 0.0252 1.0000 Uiso R . . . . . H101 H 0.4138 0.4368 0.2735 0.0248 1.0000 Uiso R . . . . . H111 H 0.3449 0.3510 0.3541 0.0209 1.0000 Uiso R . . . . . H131 H 0.0642 0.6005 0.5177 0.0505 1.0000 Uiso R . . . . . H132 H 0.0945 0.8329 0.5301 0.0509 1.0000 Uiso R . . . . . H133 H 0.0142 0.7926 0.4907 0.0487 1.0000 Uiso R . . . . . H141 H 0.0324 0.5784 0.3281 0.0433 1.0000 Uiso R . . . . . H142 H 0.0266 0.4304 0.3944 0.0452 1.0000 Uiso R . . . . . H143 H -0.0242 0.6344 0.3713 0.0439 1.0000 Uiso R . . . . . H151 H 0.0272 1.0163 0.3951 0.0435 1.0000 Uiso R . . . . . H152 H 0.1072 1.0439 0.4211 0.0443 1.0000 Uiso R . . . . . H153 H 0.0758 0.9540 0.3428 0.0444 1.0000 Uiso 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 C1 0.01473(19) 0.01191(18) 0.01484(19) 0.00280(14) 0.00494(15) 0.00178(14) C2 0.01549(19) 0.01316(19) 0.0171(2) 0.00323(16) 0.00632(16) 0.00259(15) C3 0.01336(18) 0.01222(18) 0.01455(19) 0.00106(15) 0.00368(15) 0.00140(14) C4 0.01459(19) 0.01389(19) 0.0158(2) 0.00361(16) 0.00462(15) 0.00233(15) C5 0.01387(19) 0.01269(19) 0.01432(19) 0.00245(15) 0.00433(15) 0.00130(14) C6 0.01359(19) 0.01450(19) 0.01405(18) 0.00288(15) 0.00385(15) 0.00063(15) C7 0.0173(2) 0.0156(2) 0.0194(2) 0.00469(17) 0.00604(17) 0.00111(16) C8 0.0204(2) 0.0186(2) 0.0201(2) 0.00537(18) 0.00685(19) -0.00139(18) C9 0.0218(2) 0.0228(3) 0.0194(2) 0.00252(19) 0.00926(19) -0.0020(2) C10 0.0205(2) 0.0207(2) 0.0202(2) 0.00137(19) 0.00958(19) 0.00147(19) C11 0.0183(2) 0.0162(2) 0.0174(2) 0.00246(17) 0.00706(17) 0.00198(17) C12 0.01354(19) 0.01291(19) 0.01574(19) 0.00068(15) 0.00377(15) 0.00179(14) C13 0.0266(3) 0.0566(5) 0.0205(3) 0.0073(3) 0.0107(2) 0.0198(3) C14 0.0184(3) 0.0221(3) 0.0403(4) -0.0112(3) -0.0021(2) 0.0029(2) C15 0.0228(3) 0.0151(2) 0.0532(5) 0.0100(3) 0.0167(3) 0.0061(2) N1 0.01501(17) 0.01291(17) 0.01534(17) 0.00325(14) 0.00520(14) 0.00149(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.11400(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C1 4_556 1.4943(10) yes C1 . C2 . 1.3952(7) yes C1 . N1 . 1.3412(7) yes C2 . C3 . 1.3991(7) yes C2 . H21 . 0.996 no C3 . C4 . 1.3931(7) yes C3 . C12 . 1.5297(7) yes C4 . C5 . 1.4004(7) yes C4 . H41 . 0.953 no C5 . C6 . 1.4837(7) yes C5 . N1 . 1.3414(7) yes C6 . C7 . 1.3992(8) yes C6 . C11 . 1.4005(8) yes C7 . C8 . 1.3926(8) yes C7 . H71 . 0.964 no C8 . C9 . 1.3908(9) yes C8 . H81 . 0.961 no C9 . C10 . 1.3922(9) yes C9 . H91 . 0.980 no C10 . C11 . 1.3887(8) yes C10 . H101 . 0.971 no C11 . H111 . 0.963 no C12 . C13 . 1.5302(9) yes C12 . C14 . 1.5328(9) yes C12 . C15 . 1.5275(9) yes C13 . H131 . 0.954 no C13 . H132 . 0.989 no C13 . H133 . 0.978 no C14 . H141 . 1.026 no C14 . H142 . 0.971 no C14 . H143 . 0.979 no C15 . H151 . 0.963 no C15 . H152 . 0.936 no C15 . H153 . 1.059 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 4_556 C1 . C2 . 120.73(6) yes C1 4_556 C1 . N1 . 116.32(6) yes C2 . C1 . N1 . 122.94(5) yes C1 . C2 . C3 . 119.81(5) yes C1 . C2 . H21 . 119.0 no C3 . C2 . H21 . 121.2 no C2 . C3 . C4 . 116.77(5) yes C2 . C3 . C12 . 121.13(5) yes C4 . C3 . C12 . 121.93(5) yes C3 . C4 . C5 . 120.12(5) yes C3 . C4 . H41 . 121.4 no C5 . C4 . H41 . 118.4 no C4 . C5 . C6 . 121.12(5) yes C4 . C5 . N1 . 122.51(5) yes C6 . C5 . N1 . 116.31(5) yes C5 . C6 . C7 . 122.03(5) yes C5 . C6 . C11 . 119.16(5) yes C7 . C6 . C11 . 118.81(5) yes C6 . C7 . C8 . 120.36(5) yes C6 . C7 . H71 . 117.9 no C8 . C7 . H71 . 121.7 no C7 . C8 . C9 . 120.40(6) yes C7 . C8 . H81 . 122.6 no C9 . C8 . H81 . 117.0 no C8 . C9 . C10 . 119.51(5) yes C8 . C9 . H91 . 120.5 no C10 . C9 . H91 . 120.0 no C9 . C10 . C11 . 120.31(6) yes C9 . C10 . H101 . 117.4 no C11 . C10 . H101 . 122.3 no C6 . C11 . C10 . 120.58(5) yes C6 . C11 . H111 . 115.9 no C10 . C11 . H111 . 123.5 no C3 . C12 . C13 . 111.48(5) yes C3 . C12 . C14 . 107.89(5) yes C13 . C12 . C14 . 109.17(6) yes C3 . C12 . C15 . 112.30(5) yes C13 . C12 . C15 . 107.10(6) yes C14 . C12 . C15 . 108.84(6) yes C12 . C13 . H131 . 112.0 no C12 . C13 . H132 . 114.3 no H131 . C13 . H132 . 105.0 no C12 . C13 . H133 . 111.6 no H131 . C13 . H133 . 105.5 no H132 . C13 . H133 . 107.9 no C12 . C14 . H141 . 108.2 no C12 . C14 . H142 . 110.1 no H141 . C14 . H142 . 109.8 no C12 . C14 . H143 . 110.4 no H141 . C14 . H143 . 108.8 no H142 . C14 . H143 . 109.6 no C12 . C15 . H151 . 109.6 no C12 . C15 . H152 . 110.7 no H151 . C15 . H152 . 108.3 no C12 . C15 . H153 . 111.4 no H151 . C15 . H153 . 109.3 no H152 . C15 . H153 . 107.3 no C5 . N1 . C1 . 117.83(5) yes