# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_fab1-121 _database_code_depnum_ccdc_archive 'CCDC 916564' #TrackingRef '16312_web_deposit_cif_file_0_YorkSchramm_1355932760.publish.cif' _audit_creation_date 07-11-09 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '11091630 fab1-121_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 19.4370(2) _cell_length_b 19.4370(2) _cell_length_c 18.1371(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 5934.13(11) _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M 'P 63 ' _symmetry_space_group_name_Hall 'P 6c' loop_ _symmetry_equiv_pos_as_xyz x,y,z x-y,x,z+1/2 -y,x-y,z -x,-y,z+1/2 -x+y,-x,z y,-x+y,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' Ir -1.4442 7.9887 27.3049 1.5928 16.7296 8.8655 15.6115 0.4179 5.8338 45.0011 11.4722 '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' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 6 # Given Formula = C38 H38 F6 Ir1 N2 O1 P1 # Dc = 1.47 Fooo = 2922.00 Mu = 34.73 M = 875.91 # Found Formula = C42 H44 F6 Ir1 N2 O2 P2 # Dc = 1.64 FOOO = 2922.00 Mu = 35.23 M = 976.98 _chemical_formula_sum 'C42 H44 F6 Ir1 N2 O2 P2' _chemical_formula_moiety 'C42 H44 Ir N2 O2 P, F6 P' _chemical_compound_source ? _chemical_formula_weight 976.98 _cell_measurement_reflns_used 23630 _cell_measurement_theta_min 1 _cell_measurement_theta_max 28 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2922 _exptl_absorpt_coefficient_mu 3.523 # Sheldrick geometric approximatio 0.81 0.87 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.87 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _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 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _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 173 _diffrn_reflns_number 47359 _reflns_number_total 9429 _diffrn_reflns_av_R_equivalents 0.065 # Number of reflections with Friedels Law is 4866 # Number of reflections without Friedels Law is 9429 # Theoretical number of reflections is about 4712 _diffrn_reflns_theta_min 1.210 _diffrn_reflns_theta_max 27.863 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.863 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -21 _reflns_limit_h_max 0 _reflns_limit_k_min 0 _reflns_limit_k_max 25 _reflns_limit_l_min -23 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.48 _refine_diff_density_max 1.77 _refine_ls_number_reflns 5400 _refine_ls_number_restraints 1 _refine_ls_number_parameters 497 #_refine_ls_R_factor_ref 0.0216 _refine_ls_wR_factor_ref 0.0196 _refine_ls_goodness_of_fit_ref 0.7012 #_reflns_number_all 9329 _refine_ls_R_factor_all 0.0497 _refine_ls_wR_factor_all 0.0234 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 5400 _refine_ls_R_factor_gt 0.0216 _refine_ls_wR_factor_gt 0.0196 _refine_ls_shift/su_max 0.003822 _refine_ls_abs_structure_Flack 0.012(5) _refine_ls_abs_structure_details 'Flack (1983), 4563 Friedel-pairs' # 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 ad _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; 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 Ir1 Ir 0.327810(9) 0.350321(9) 0.40278(4) 0.0270 1.0000 Uani . . . . . . P1 P 0.30935(9) 0.33670(9) 0.52966(8) 0.0291 1.0000 Uani . . . . . . P2 P 0.0000 0.0000 0.35910(13) 0.0333 1.0000 Uani S T . . . . P3 P 0.6667 0.3333 0.37717(13) 0.0484 1.0000 Uani S T . . . . P4 P 0.6667 0.3333 0.82362(17) 0.0665 1.0000 Uani S T . . . . N1 N 0.4454(2) 0.4217(2) 0.42713(18) 0.0298 1.0000 Uani . . . . . . N2 N 0.3512(2) 0.2540(2) 0.37279(19) 0.0311 1.0000 Uani . . . . . . O1 O 0.5646(2) 0.4724(2) 0.47960(18) 0.0419 1.0000 Uani . . . . . . O2 O 0.20680(19) 0.28120(19) 0.37045(16) 0.0358 1.0000 Uani . . . . . . F1 F 0.0213(2) -0.0530(2) 0.4090(3) 0.0920 1.0000 Uani . . . . . . F2 F 0.0742(2) 0.0215(2) 0.3091(2) 0.0852 1.0000 Uani . . . . . . F3 F 0.6409(5) 0.2614(4) 0.3278(4) 0.2212 1.0000 Uani . . . . . . F4 F 0.5938(3) 0.2832(3) 0.4237(4) 0.1734 1.0000 Uani . . . . . . F5 F 0.5914(3) 0.3009(3) 0.8722(3) 0.1528 1.0000 Uani . . . . . . F6 F 0.6367(3) 0.3793(3) 0.7721(2) 0.1154 1.0000 Uani . . . . . . C1 C 0.4991(3) 0.4909(3) 0.3791(2) 0.0360 1.0000 Uani . . . . . . C2 C 0.5804(2) 0.5101(3) 0.4066(5) 0.0456 1.0000 Uani . . . . . . C3 C 0.4869(3) 0.4186(3) 0.4807(3) 0.0308 1.0000 Uani . . . . . . C4 C 0.4637(3) 0.3624(3) 0.5428(3) 0.0319 1.0000 Uani . . . . . . C5 C 0.5234(3) 0.3526(3) 0.5742(2) 0.0370 1.0000 Uani . . . . . . C6 C 0.5069(3) 0.2998(3) 0.6321(3) 0.0431 1.0000 Uani . . . . . . C7 C 0.4296(4) 0.2557(3) 0.6576(3) 0.0457 1.0000 Uani . . . . . . C8 C 0.3706(3) 0.2658(3) 0.6274(2) 0.0402 1.0000 Uani . . . . . . C9 C 0.3851(4) 0.3190(4) 0.5690(3) 0.0291 1.0000 Uani . . . . . . C10 C 0.2172(3) 0.2633(3) 0.5740(2) 0.0301 1.0000 Uani . . . . . . C11 C 0.1613(4) 0.1984(4) 0.5358(3) 0.0500 1.0000 Uani . . . . . . C12 C 0.0921(4) 0.1407(4) 0.5696(3) 0.0579 1.0000 Uani . . . . . . C13 C 0.0768(3) 0.1480(3) 0.6412(3) 0.0529 1.0000 Uani . . . . . . C14 C 0.1331(4) 0.2111(4) 0.6827(3) 0.0559 1.0000 Uani . . . . . . C15 C 0.2030(3) 0.2687(3) 0.6491(3) 0.0503 1.0000 Uani . . . . . . C16 C 0.3286(3) 0.4276(4) 0.5774(3) 0.0290 1.0000 Uani . . . . . . C17 C 0.2906(3) 0.4673(3) 0.5529(3) 0.0431 1.0000 Uani . . . . . . C18 C 0.2981(3) 0.5321(3) 0.5900(3) 0.0474 1.0000 Uani . . . . . . C19 C 0.3434(3) 0.5588(3) 0.6531(3) 0.0450 1.0000 Uani . . . . . . C20 C 0.3821(3) 0.5206(3) 0.6778(3) 0.0403 1.0000 Uani . . . . . . C21 C 0.3737(4) 0.4541(4) 0.6407(4) 0.0375 1.0000 Uani . . . . . . C22 C 0.4829(3) 0.5598(3) 0.3818(3) 0.0394 1.0000 Uani . . . . . . C23 C 0.5309(4) 0.6201(4) 0.3223(4) 0.0628 1.0000 Uani . . . . . . C24 C 0.4971(4) 0.5989(4) 0.4581(3) 0.0512 1.0000 Uani . . . . . . C25 C 0.3577(4) 0.3716(4) 0.2927(3) 0.0404 1.0000 Uani . . . . . . C26 C 0.3540(4) 0.4294(4) 0.2487(3) 0.0421 1.0000 Uani . . . . . . C27 C 0.3825(4) 0.4439(5) 0.1770(4) 0.0554 1.0000 Uani . . . . . . C28 C 0.4123(3) 0.3990(5) 0.1486(3) 0.0634 1.0000 Uani . . . . . . C29 C 0.4135(4) 0.3386(4) 0.1891(3) 0.0564 1.0000 Uani . . . . . . C30 C 0.3855(4) 0.3257(4) 0.2619(3) 0.0377 1.0000 Uani . . . . . . C31 C 0.3821(3) 0.2619(3) 0.3079(3) 0.0381 1.0000 Uani . . . . . . C32 C 0.4117(4) 0.2084(4) 0.2802(3) 0.0578 1.0000 Uani . . . . . . C33 C 0.3380(3) 0.1899(3) 0.4203(2) 0.0321 1.0000 Uani . . . . . . C34 C 0.3992(3) 0.1905(3) 0.4586(3) 0.0412 1.0000 Uani . . . . . . C35 C 0.3825(4) 0.1289(4) 0.5087(3) 0.0550 1.0000 Uani . . . . . . C36 C 0.3074(5) 0.0689(4) 0.5198(3) 0.0600 1.0000 Uani . . . . . . C37 C 0.2465(4) 0.0674(4) 0.4799(4) 0.0637 1.0000 Uani . . . . . . C38 C 0.2618(4) 0.1283(3) 0.4299(3) 0.0531 1.0000 Uani . . . . . . C39 C 0.1830(4) 0.2265(4) 0.3075(3) 0.0475 1.0000 Uani . . . . . . C40 C 0.1262(4) 0.2400(4) 0.2634(3) 0.0647 1.0000 Uani . . . . . . C41 C 0.0878(4) 0.2650(4) 0.3206(4) 0.0668 1.0000 Uani . . . . . . C42 C 0.1572(3) 0.3170(4) 0.3718(3) 0.0582 1.0000 Uani . . . . . . H11 H 0.4924 0.4717 0.3281 0.0411 1.0000 Uiso R . . . . . H21 H 0.6043 0.4876 0.3747 0.0532 1.0000 Uiso R . . . . . H22 H 0.6158 0.5672 0.4111 0.0531 1.0000 Uiso R . . . . . H51 H 0.5752 0.3819 0.5561 0.0470 1.0000 Uiso R . . . . . H61 H 0.5473 0.2942 0.6541 0.0592 1.0000 Uiso R . . . . . H71 H 0.4173 0.2187 0.6956 0.0610 1.0000 Uiso R . . . . . H81 H 0.3191 0.2365 0.6460 0.0541 1.0000 Uiso R . . . . . H111 H 0.1703 0.1931 0.4859 0.0564 1.0000 Uiso R . . . . . H121 H 0.0555 0.0962 0.5434 0.0632 1.0000 Uiso R . . . . . H131 H 0.0289 0.1112 0.6633 0.0603 1.0000 Uiso R . . . . . H141 H 0.1246 0.2148 0.7328 0.0621 1.0000 Uiso R . . . . . H151 H 0.2407 0.3120 0.6772 0.0552 1.0000 Uiso R . . . . . H171 H 0.2591 0.4486 0.5106 0.0572 1.0000 Uiso R . . . . . H181 H 0.2719 0.5583 0.5723 0.0671 1.0000 Uiso R . . . . . H191 H 0.3484 0.6029 0.6794 0.0542 1.0000 Uiso R . . . . . H201 H 0.4138 0.5385 0.7201 0.0452 1.0000 Uiso R . . . . . H211 H 0.3995 0.4279 0.6583 0.0485 1.0000 Uiso R . . . . . H221 H 0.4269 0.5387 0.3705 0.0470 1.0000 Uiso R . . . . . H231 H 0.5172 0.6614 0.3201 0.0861 1.0000 Uiso R . . . . . H232 H 0.5204 0.5935 0.2751 0.0863 1.0000 Uiso R . . . . . H233 H 0.5865 0.6435 0.3342 0.0861 1.0000 Uiso R . . . . . H241 H 0.4804 0.6378 0.4583 0.0779 1.0000 Uiso R . . . . . H242 H 0.4682 0.5586 0.4950 0.0780 1.0000 Uiso R . . . . . H243 H 0.5531 0.6239 0.4672 0.0783 1.0000 Uiso R . . . . . H261 H 0.3335 0.4596 0.2681 0.0474 1.0000 Uiso R . . . . . H271 H 0.3795 0.4822 0.1481 0.0544 1.0000 Uiso R . . . . . H281 H 0.4331 0.4100 0.1008 0.0602 1.0000 Uiso R . . . . . H291 H 0.4331 0.3082 0.1679 0.0673 1.0000 Uiso R . . . . . H321 H 0.4047 0.2027 0.2275 0.0929 1.0000 Uiso R . . . . . H322 H 0.3825 0.1565 0.3025 0.0930 1.0000 Uiso R . . . . . H323 H 0.4671 0.2318 0.2915 0.0932 1.0000 Uiso R . . . . . H341 H 0.4513 0.2315 0.4511 0.0632 1.0000 Uiso R . . . . . H351 H 0.4240 0.1292 0.5351 0.0800 1.0000 Uiso R . . . . . H361 H 0.2982 0.0290 0.5537 0.0809 1.0000 Uiso R . . . . . H371 H 0.1947 0.0260 0.4875 0.0772 1.0000 Uiso R . . . . . H381 H 0.2200 0.1269 0.4022 0.0671 1.0000 Uiso R . . . . . H391 H 0.1572 0.1717 0.3259 0.0642 1.0000 Uiso R . . . . . H392 H 0.2297 0.2372 0.2779 0.0641 1.0000 Uiso R . . . . . H401 H 0.0868 0.1918 0.2380 0.0810 1.0000 Uiso R . . . . . H402 H 0.1551 0.2827 0.2275 0.0810 1.0000 Uiso R . . . . . H411 H 0.0481 0.2191 0.3483 0.0901 1.0000 Uiso R . . . . . H412 H 0.0637 0.2938 0.2992 0.0900 1.0000 Uiso R . . . . . H421 H 0.1395 0.3166 0.4216 0.0813 1.0000 Uiso R . . . . . H422 H 0.1864 0.3715 0.3540 0.0810 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 Ir1 0.02722(9) 0.03019(10) 0.02155(7) 0.0018(2) 0.00157(18) 0.01277(8) P1 0.0352(9) 0.0320(9) 0.0231(7) 0.0006(6) 0.0031(6) 0.0190(7) P2 0.0321(8) 0.0321(8) 0.0358(12) 0.0000 0.0000 0.0160(4) P3 0.0472(10) 0.0472(10) 0.0507(18) 0.0000 0.0000 0.0236(5) P4 0.0695(14) 0.0695(14) 0.0607(19) 0.0000 0.0000 0.0347(7) N1 0.027(2) 0.026(2) 0.030(3) -0.0019(16) -0.0034(16) 0.008(2) N2 0.027(2) 0.032(3) 0.032(2) -0.0095(18) -0.0033(17) 0.013(2) O1 0.034(2) 0.041(2) 0.039(2) 0.0082(17) -0.0044(16) 0.010(2) O2 0.029(2) 0.039(2) 0.037(2) 0.0034(15) -0.0059(14) 0.0152(18) F1 0.129(3) 0.091(2) 0.083(3) 0.025(3) -0.023(4) 0.075(2) F2 0.064(3) 0.106(3) 0.086(3) 0.011(2) 0.038(2) 0.043(3) F3 0.231(8) 0.181(6) 0.225(7) -0.127(5) -0.018(6) 0.084(7) F4 0.084(3) 0.139(4) 0.231(10) 0.011(5) 0.078(5) 0.007(3) F5 0.125(4) 0.172(5) 0.137(5) 0.012(3) 0.059(3) 0.056(4) F6 0.130(4) 0.109(4) 0.122(4) 0.009(3) -0.023(3) 0.070(3) C1 0.029(3) 0.034(3) 0.032(3) 0.006(2) 0.002(2) 0.006(3) C2 0.036(3) 0.040(3) 0.045(3) 0.007(5) -0.001(5) 0.007(2) C3 0.030(3) 0.030(3) 0.033(3) -0.004(2) -0.002(2) 0.015(3) C4 0.035(3) 0.030(3) 0.030(3) -0.008(2) -0.006(2) 0.016(3) C5 0.034(3) 0.040(3) 0.036(3) -0.004(2) -0.005(2) 0.018(3) C6 0.055(4) 0.054(4) 0.036(3) -0.003(3) -0.012(3) 0.039(3) C7 0.072(4) 0.055(4) 0.024(3) 0.009(3) 0.006(3) 0.041(4) C8 0.051(4) 0.049(4) 0.031(3) 0.005(3) 0.007(3) 0.033(3) C9 0.042(4) 0.036(4) 0.019(3) -0.002(3) -0.001(3) 0.027(3) C10 0.031(3) 0.032(3) 0.026(3) 0.003(2) 0.007(2) 0.015(3) C11 0.055(4) 0.050(4) 0.038(3) 0.001(3) 0.011(3) 0.020(4) C12 0.059(4) 0.045(4) 0.043(4) 0.003(3) 0.000(3) 0.006(3) C13 0.035(4) 0.050(4) 0.060(4) 0.008(3) 0.016(3) 0.011(3) C14 0.054(4) 0.064(4) 0.042(3) 0.005(3) 0.021(3) 0.023(4) C15 0.052(4) 0.038(4) 0.050(3) -0.003(3) 0.014(3) 0.014(3) C16 0.031(4) 0.028(3) 0.030(3) 0.001(3) 0.008(3) 0.016(3) C17 0.052(4) 0.052(4) 0.039(3) -0.005(3) -0.002(3) 0.036(3) C18 0.064(4) 0.045(4) 0.048(4) 0.000(3) 0.003(3) 0.038(3) C19 0.054(4) 0.030(3) 0.047(3) -0.001(3) 0.016(3) 0.019(3) C20 0.037(3) 0.034(3) 0.039(3) -0.009(3) 0.005(2) 0.009(3) C21 0.035(4) 0.042(4) 0.033(3) 0.004(3) 0.004(3) 0.017(3) C22 0.035(3) 0.032(3) 0.038(4) 0.003(2) -0.010(2) 0.007(3) C23 0.065(5) 0.052(5) 0.055(4) 0.020(3) 0.003(4) 0.017(4) C24 0.077(5) 0.036(4) 0.040(4) 0.001(3) -0.002(3) 0.028(4) C25 0.037(4) 0.051(4) 0.022(3) 0.002(3) 0.002(3) 0.014(3) C26 0.036(4) 0.055(4) 0.024(3) 0.004(3) -0.006(3) 0.014(4) C27 0.037(5) 0.066(6) 0.040(4) 0.007(4) -0.009(4) 0.008(4) C28 0.038(4) 0.084(5) 0.032(3) 0.006(4) 0.002(3) 0.004(4) C29 0.038(4) 0.075(5) 0.042(4) -0.017(4) -0.005(3) 0.018(4) C30 0.027(4) 0.047(4) 0.024(3) -0.008(3) 0.000(3) 0.008(3) C31 0.029(3) 0.048(4) 0.031(3) -0.017(3) -0.003(2) 0.015(3) C32 0.047(4) 0.080(5) 0.055(4) -0.025(3) -0.005(3) 0.038(4) C33 0.033(3) 0.037(3) 0.031(4) -0.006(2) 0.004(2) 0.020(3) C34 0.040(3) 0.048(4) 0.047(3) -0.015(3) -0.012(3) 0.031(3) C35 0.077(5) 0.070(5) 0.050(4) -0.025(3) -0.021(3) 0.061(5) C36 0.078(5) 0.063(5) 0.061(4) 0.006(3) 0.006(4) 0.051(5) C37 0.047(4) 0.045(4) 0.097(5) 0.020(4) 0.005(4) 0.021(3) C38 0.047(4) 0.042(4) 0.067(5) 0.011(3) 0.001(3) 0.019(3) C39 0.041(4) 0.053(4) 0.044(4) 0.000(3) -0.003(3) 0.019(3) C40 0.078(5) 0.053(4) 0.066(4) -0.005(3) -0.030(4) 0.036(4) C41 0.048(4) 0.062(5) 0.094(5) -0.011(4) -0.028(4) 0.030(4) C42 0.048(4) 0.065(4) 0.079(4) -0.008(3) -0.012(3) 0.040(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.05380(3) 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 Ir1 . P1 . 2.3237(13) yes Ir1 . N1 . 2.044(4) yes Ir1 . N2 . 2.205(4) yes Ir1 . O2 . 2.126(3) yes Ir1 . C25 . 2.063(5) yes P1 . C9 . 1.818(7) yes P1 . C10 . 1.827(5) yes P1 . C16 . 1.831(6) yes P2 . F1 5_555 1.574(4) yes P2 . F1 3_555 1.574(4) yes P2 . F2 5_555 1.573(3) yes P2 . F2 3_555 1.573(3) yes P2 . F1 . 1.574(4) yes P2 . F2 . 1.573(3) yes P3 . F3 3_655 1.519(6) yes P3 . F3 5_665 1.519(6) yes P3 . F4 3_655 1.513(5) yes P3 . F4 5_665 1.513(5) yes P3 . F3 . 1.519(6) yes P3 . F4 . 1.513(5) yes P4 . F6 5_665 1.591(4) yes P4 . F6 3_655 1.591(4) yes P4 . F5 5_665 1.547(5) yes P4 . F5 3_655 1.547(5) yes P4 . F5 . 1.547(5) yes P4 . F6 . 1.591(4) yes N1 . C1 . 1.500(5) yes N1 . C3 . 1.283(5) yes N2 . C31 . 1.295(5) yes N2 . C33 . 1.428(5) yes O1 . C2 . 1.469(8) yes O1 . C3 . 1.341(5) yes O2 . C39 . 1.470(6) yes O2 . C42 . 1.443(6) yes C1 . C2 . 1.514(7) yes C1 . C22 . 1.523(7) yes C1 . H11 . 0.982 no C2 . H21 . 0.973 no C2 . H22 . 0.974 no C3 . C4 . 1.474(7) yes C4 . C5 . 1.388(6) yes C4 . C9 . 1.408(8) yes C5 . C6 . 1.390(7) yes C5 . H51 . 0.934 no C6 . C7 . 1.385(7) yes C6 . H61 . 0.934 no C7 . C8 . 1.372(7) yes C7 . H71 . 0.936 no C8 . C9 . 1.405(7) yes C8 . H81 . 0.932 no C10 . C11 . 1.370(7) yes C10 . C15 . 1.404(7) yes C11 . C12 . 1.391(7) yes C11 . H111 . 0.936 no C12 . C13 . 1.356(7) yes C12 . H121 . 0.930 no C13 . C14 . 1.387(7) yes C13 . H131 . 0.934 no C14 . C15 . 1.396(7) yes C14 . H141 . 0.933 no C15 . H151 . 0.944 no C16 . C17 . 1.383(7) yes C16 . C21 . 1.377(8) yes C17 . C18 . 1.370(7) yes C17 . H171 . 0.934 no C18 . C19 . 1.378(7) yes C18 . H181 . 0.937 no C19 . C20 . 1.369(7) yes C19 . H191 . 0.943 no C20 . C21 . 1.394(8) yes C20 . H201 . 0.935 no C21 . H211 . 0.932 no C22 . C23 . 1.522(7) yes C22 . C24 . 1.536(7) yes C22 . H221 . 0.975 no C23 . H231 . 0.966 no C23 . H232 . 0.968 no C23 . H233 . 0.965 no C24 . H241 . 0.960 no C24 . H242 . 0.967 no C24 . H243 . 0.959 no C25 . C26 . 1.408(8) yes C25 . C30 . 1.373(9) yes C26 . C27 . 1.384(8) yes C26 . H261 . 0.928 no C27 . C28 . 1.368(10) yes C27 . H271 . 0.936 no C28 . C29 . 1.394(9) yes C28 . H281 . 0.936 no C29 . C30 . 1.402(8) yes C29 . H291 . 0.932 no C30 . C31 . 1.467(9) yes C31 . C32 . 1.504(7) yes C32 . H321 . 0.965 no C32 . H322 . 0.965 no C32 . H323 . 0.959 no C33 . C34 . 1.372(7) yes C33 . C38 . 1.372(7) yes C34 . C35 . 1.405(8) yes C34 . H341 . 0.933 no C35 . C36 . 1.353(8) yes C35 . H351 . 0.936 no C36 . C37 . 1.375(8) yes C36 . H361 . 0.934 no C37 . C38 . 1.401(7) yes C37 . H371 . 0.932 no C38 . H381 . 0.945 no C39 . C40 . 1.490(8) yes C39 . H391 . 0.980 no C39 . H392 . 0.982 no C40 . C41 . 1.494(8) yes C40 . H401 . 0.980 no C40 . H402 . 0.982 no C41 . C42 . 1.529(7) yes C41 . H411 . 0.977 no C41 . H412 . 0.973 no C42 . H421 . 0.965 no C42 . H422 . 0.973 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 P1 . Ir1 . N1 . 85.41(10) yes P1 . Ir1 . N2 . 103.49(10) yes N1 . Ir1 . N2 . 89.68(14) yes P1 . Ir1 . O2 . 98.17(9) yes N1 . Ir1 . O2 . 175.80(13) yes N2 . Ir1 . O2 . 91.61(13) yes P1 . Ir1 . C25 . 173.43(19) yes N1 . Ir1 . C25 . 88.04(19) yes N2 . Ir1 . C25 . 77.0(2) yes O2 . Ir1 . C25 . 88.35(19) yes Ir1 . P1 . C9 . 108.5(2) yes Ir1 . P1 . C10 . 124.05(16) yes C9 . P1 . C10 . 104.5(3) yes Ir1 . P1 . C16 . 114.43(19) yes C9 . P1 . C16 . 101.7(3) yes C10 . P1 . C16 . 101.2(2) yes F1 5_555 P2 . F1 3_555 90.2(3) yes F1 5_555 P2 . F2 5_555 90.0(2) yes F1 3_555 P2 . F2 5_555 179.8(2) yes F1 5_555 P2 . F2 3_555 89.7(2) yes F1 3_555 P2 . F2 3_555 90.0(2) yes F2 5_555 P2 . F2 3_555 90.0(2) yes F1 5_555 P2 . F1 . 90.2(3) yes F1 3_555 P2 . F1 . 90.2(3) yes F2 5_555 P2 . F1 . 89.7(2) yes F2 3_555 P2 . F1 . 179.8(2) yes F1 5_555 P2 . F2 . 179.8(2) yes F1 3_555 P2 . F2 . 89.7(2) yes F2 5_555 P2 . F2 . 90.0(2) yes F2 3_555 P2 . F2 . 90.0(2) yes F1 . P2 . F2 . 90.0(2) yes F3 3_655 P3 . F3 5_665 88.8(5) yes F3 3_655 P3 . F4 3_655 88.0(4) yes F3 5_665 P3 . F4 3_655 176.8(4) yes F3 3_655 P3 . F4 5_665 91.4(4) yes F3 5_665 P3 . F4 5_665 88.0(4) yes F4 3_655 P3 . F4 5_665 91.8(4) yes F3 3_655 P3 . F3 . 88.8(5) yes F3 5_665 P3 . F3 . 88.8(5) yes F4 3_655 P3 . F3 . 91.4(4) yes F4 5_665 P3 . F3 . 176.8(4) yes F3 3_655 P3 . F4 . 176.8(4) yes F3 5_665 P3 . F4 . 91.4(4) yes F4 3_655 P3 . F4 . 91.8(4) yes F4 5_665 P3 . F4 . 91.8(4) yes F3 . P3 . F4 . 88.0(4) yes F6 5_665 P4 . F6 3_655 89.0(3) yes F6 5_665 P4 . F5 5_665 91.5(3) yes F6 3_655 P4 . F5 5_665 177.7(3) yes F6 5_665 P4 . F5 3_655 88.8(3) yes F6 3_655 P4 . F5 3_655 91.5(3) yes F5 5_665 P4 . F5 3_655 90.7(3) yes F6 5_665 P4 . F5 . 177.7(3) yes F6 3_655 P4 . F5 . 88.8(3) yes F5 5_665 P4 . F5 . 90.7(3) yes F5 3_655 P4 . F5 . 90.7(3) yes F6 5_665 P4 . F6 . 89.0(3) yes F6 3_655 P4 . F6 . 89.0(3) yes F5 5_665 P4 . F6 . 88.8(3) yes F5 3_655 P4 . F6 . 177.7(3) yes F5 . P4 . F6 . 91.5(3) yes Ir1 . N1 . C1 . 121.6(3) yes Ir1 . N1 . C3 . 130.3(3) yes C1 . N1 . C3 . 108.1(4) yes Ir1 . N2 . C31 . 113.8(4) yes Ir1 . N2 . C33 . 124.6(3) yes C31 . N2 . C33 . 121.5(4) yes C2 . O1 . C3 . 106.0(3) yes Ir1 . O2 . C39 . 121.3(3) yes Ir1 . O2 . C42 . 119.0(3) yes C39 . O2 . C42 . 108.6(4) yes N1 . C1 . C2 . 101.7(4) yes N1 . C1 . C22 . 114.3(4) yes C2 . C1 . C22 . 114.9(4) yes N1 . C1 . H11 . 107.9 no C2 . C1 . H11 . 109.2 no C22 . C1 . H11 . 108.5 no C1 . C2 . O1 . 104.0(4) yes C1 . C2 . H21 . 111.5 no O1 . C2 . H21 . 109.9 no C1 . C2 . H22 . 111.4 no O1 . C2 . H22 . 110.2 no H21 . C2 . H22 . 109.7 no O1 . C3 . N1 . 116.2(4) yes O1 . C3 . C4 . 113.4(4) yes N1 . C3 . C4 . 130.4(5) yes C3 . C4 . C5 . 116.6(5) yes C3 . C4 . C9 . 122.7(5) yes C5 . C4 . C9 . 120.7(5) yes C4 . C5 . C6 . 120.7(5) yes C4 . C5 . H51 . 119.6 no C6 . C5 . H51 . 119.7 no C5 . C6 . C7 . 119.2(5) yes C5 . C6 . H61 . 120.7 no C7 . C6 . H61 . 120.0 no C6 . C7 . C8 . 120.2(5) yes C6 . C7 . H71 . 120.2 no C8 . C7 . H71 . 119.5 no C7 . C8 . C9 . 122.1(6) yes C7 . C8 . H81 . 119.1 no C9 . C8 . H81 . 118.8 no P1 . C9 . C4 . 119.5(4) yes P1 . C9 . C8 . 123.5(5) yes C4 . C9 . C8 . 117.0(6) yes P1 . C10 . C11 . 120.9(4) yes P1 . C10 . C15 . 121.4(4) yes C11 . C10 . C15 . 117.6(5) yes C10 . C11 . C12 . 121.4(5) yes C10 . C11 . H111 . 118.9 no C12 . C11 . H111 . 119.7 no C11 . C12 . C13 . 120.8(6) yes C11 . C12 . H121 . 120.4 no C13 . C12 . H121 . 118.7 no C12 . C13 . C14 . 119.6(5) yes C12 . C13 . H131 . 121.1 no C14 . C13 . H131 . 119.2 no C13 . C14 . C15 . 119.5(5) yes C13 . C14 . H141 . 120.3 no C15 . C14 . H141 . 120.1 no C10 . C15 . C14 . 120.8(5) yes C10 . C15 . H151 . 119.8 no C14 . C15 . H151 . 119.3 no P1 . C16 . C17 . 118.6(4) yes P1 . C16 . C21 . 122.7(5) yes C17 . C16 . C21 . 118.5(6) yes C16 . C17 . C18 . 121.0(5) yes C16 . C17 . H171 . 118.5 no C18 . C17 . H171 . 120.5 no C17 . C18 . C19 . 120.5(5) yes C17 . C18 . H181 . 119.6 no C19 . C18 . H181 . 120.0 no C18 . C19 . C20 . 119.3(5) yes C18 . C19 . H191 . 121.1 no C20 . C19 . H191 . 119.5 no C19 . C20 . C21 . 120.2(5) yes C19 . C20 . H201 . 120.4 no C21 . C20 . H201 . 119.4 no C20 . C21 . C16 . 120.5(6) yes C20 . C21 . H211 . 119.7 no C16 . C21 . H211 . 119.8 no C1 . C22 . C23 . 109.7(5) yes C1 . C22 . C24 . 113.6(4) yes C23 . C22 . C24 . 111.6(5) yes C1 . C22 . H221 . 107.6 no C23 . C22 . H221 . 107.4 no C24 . C22 . H221 . 106.5 no C22 . C23 . H231 . 110.6 no C22 . C23 . H232 . 109.4 no H231 . C23 . H232 . 109.7 no C22 . C23 . H233 . 108.4 no H231 . C23 . H233 . 109.0 no H232 . C23 . H233 . 109.7 no C22 . C24 . H241 . 110.2 no C22 . C24 . H242 . 109.4 no H241 . C24 . H242 . 110.4 no C22 . C24 . H243 . 106.5 no H241 . C24 . H243 . 110.3 no H242 . C24 . H243 . 110.0 no Ir1 . C25 . C26 . 126.0(5) yes Ir1 . C25 . C30 . 115.2(5) yes C26 . C25 . C30 . 118.8(6) yes C25 . C26 . C27 . 121.3(7) yes C25 . C26 . H261 . 119.9 no C27 . C26 . H261 . 118.7 no C26 . C27 . C28 . 118.5(7) yes C26 . C27 . H271 . 120.7 no C28 . C27 . H271 . 120.7 no C27 . C28 . C29 . 122.0(6) yes C27 . C28 . H281 . 118.4 no C29 . C28 . H281 . 119.6 no C28 . C29 . C30 . 118.6(7) yes C28 . C29 . H291 . 120.1 no C30 . C29 . H291 . 121.3 no C29 . C30 . C25 . 120.6(7) yes C29 . C30 . C31 . 122.4(7) yes C25 . C30 . C31 . 116.9(5) yes C30 . C31 . N2 . 116.0(5) yes C30 . C31 . C32 . 121.6(5) yes N2 . C31 . C32 . 122.4(5) yes C31 . C32 . H321 . 109.2 no C31 . C32 . H322 . 110.9 no H321 . C32 . H322 . 108.6 no C31 . C32 . H323 . 109.1 no H321 . C32 . H323 . 109.0 no H322 . C32 . H323 . 109.9 no N2 . C33 . C34 . 121.4(5) yes N2 . C33 . C38 . 118.8(5) yes C34 . C33 . C38 . 119.8(5) yes C33 . C34 . C35 . 119.3(5) yes C33 . C34 . H341 . 120.0 no C35 . C34 . H341 . 120.7 no C34 . C35 . C36 . 121.5(6) yes C34 . C35 . H351 . 119.6 no C36 . C35 . H351 . 118.9 no C35 . C36 . C37 . 119.0(6) yes C35 . C36 . H361 . 119.4 no C37 . C36 . H361 . 121.6 no C36 . C37 . C38 . 120.4(6) yes C36 . C37 . H371 . 119.1 no C38 . C37 . H371 . 120.5 no C37 . C38 . C33 . 120.0(5) yes C37 . C38 . H381 . 120.3 no C33 . C38 . H381 . 119.7 no O2 . C39 . C40 . 106.3(5) yes O2 . C39 . H391 . 109.0 no C40 . C39 . H391 . 110.6 no O2 . C39 . H392 . 110.3 no C40 . C39 . H392 . 111.0 no H391 . C39 . H392 . 109.5 no C39 . C40 . C41 . 102.7(5) yes C39 . C40 . H401 . 112.2 no C41 . C40 . H401 . 111.1 no C39 . C40 . H402 . 110.2 no C41 . C40 . H402 . 110.7 no H401 . C40 . H402 . 109.9 no C40 . C41 . C42 . 102.5(5) yes C40 . C41 . H411 . 110.7 no C42 . C41 . H411 . 109.0 no C40 . C41 . H412 . 111.9 no C42 . C41 . H412 . 112.5 no H411 . C41 . H412 . 110.0 no C41 . C42 . O2 . 104.7(4) yes C41 . C42 . H421 . 111.7 no O2 . C42 . H421 . 109.5 no C41 . C42 . H422 . 111.0 no O2 . C42 . H422 . 110.7 no H421 . C42 . H422 . 109.2 no