data_rob727_mo _audit_creation_date 2014-10-16 _audit_creation_method ; Olex2 1.2 (compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H28 Ir N3, 2(Cl), 4(O)' _chemical_formula_sum 'C22 H36 Cl2 Ir N3 O4' _chemical_formula_weight 669.64 _chemical_melting_point ? _chemical_oxdiff_formula 'C88 H144 Cl8 Ir4 N12 O16' 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' 'Cl' 'Cl' 0.1484 0.1585 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.3537(5) _cell_length_b 16.9867(6) _cell_length_c 12.4060(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.335(4) _cell_angle_gamma 90.00 _cell_volume 2533.22(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7321 _cell_measurement_temperature 120.03(10) _cell_measurement_theta_max 30.8330 _cell_measurement_theta_min 3.5770 _exptl_absorpt_coefficient_mu 5.514 _exptl_absorpt_correction_T_max 0.663 _exptl_absorpt_correction_T_min 0.410 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1328 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_unetI/netI 0.0667 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 16470 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.91 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 120.03(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.3095 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -48.00 -2.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - 13.1072 -57.0000 120.0000 46 #__ type_ start__ end____ width___ exp.time_ 2 omega -67.00 7.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - -13.8884 -37.0000 -120.0000 74 #__ type_ start__ end____ width___ exp.time_ 3 omega 3.00 49.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - -13.8884 37.0000 -150.0000 46 #__ type_ start__ end____ width___ exp.time_ 4 omega -56.00 -26.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - 13.1072 -19.0000 0.0000 30 #__ type_ start__ end____ width___ exp.time_ 5 omega 15.00 41.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - 13.1072 -19.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 6 omega -10.00 38.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - 13.1072 57.0000 90.0000 48 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0299041000 _diffrn_orient_matrix_UB_12 -0.0030775000 _diffrn_orient_matrix_UB_13 0.0423095000 _diffrn_orient_matrix_UB_21 -0.0165737000 _diffrn_orient_matrix_UB_22 -0.0387004000 _diffrn_orient_matrix_UB_23 -0.0178807000 _diffrn_orient_matrix_UB_31 0.0481183000 _diffrn_orient_matrix_UB_32 -0.0152627000 _diffrn_orient_matrix_UB_33 0.0366716000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4295 _reflns_number_total 5014 _reflns_odcompleteness_completeness 96.29 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.006 _refine_diff_density_min -0.734 _refine_diff_density_rms 0.190 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 293 _refine_ls_number_reflns 5014 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0377 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0868 _refine_ls_wR_factor_ref 0.0945 _refine_special_details ; The chloride anions were located in the Fourier Map as the two largest residual electron density peaks outside the iridium complex. The four remaining large electron density peaks were modelled as oxygen atoms of water molecules. The hydrogen atoms of these water molecules could not be located in the Fourier Map and were not included in the refinement process. However, the hydrogen atoms have been added to the molecular formula in the .cif file. 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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: N1(H1A,H1B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B) 2.b Aromatic/amide H refined with riding coordinates: C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22) 2.c Idealised Me refined as rotating group: C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Ir1 Ir 0.336374(16) 0.150224(11) 0.637850(15) 0.01312(9) Uani 1 d . . . N1 N 0.3730(4) 0.0879(3) 0.5034(4) 0.0193(10) Uani 1 d . . . H1A H 0.4417 0.1018 0.4974 0.023 Uiso 1 calc . . R H1B H 0.3751 0.0362 0.5198 0.023 Uiso 1 calc . . R C1 C 0.2060(4) 0.2374(3) 0.5915(4) 0.0190(12) Uani 1 d . . . N2 N 0.4558(4) 0.0781(2) 0.7362(3) 0.0160(9) Uani 1 d . . . C2 C 0.2461(4) 0.2371(3) 0.7112(4) 0.0167(11) Uani 1 d . . . N3 N 0.4856(3) 0.2099(3) 0.6440(3) 0.0143(9) Uani 1 d . . . C3 C 0.2248(5) 0.1610(3) 0.7502(5) 0.0182(12) Uani 1 d . . . C4 C 0.1745(4) 0.1128(3) 0.6561(4) 0.0172(11) Uani 1 d . . . C5 C 0.1612(4) 0.1610(3) 0.5584(4) 0.0160(11) Uani 1 d . . . C6 C 0.1994(5) 0.3073(3) 0.5166(5) 0.0215(12) Uani 1 d . . . H6A H 0.2501 0.3472 0.5526 0.032 Uiso 1 calc . . GR H6B H 0.1249 0.3279 0.5000 0.032 Uiso 1 calc . . GR H6C H 0.2188 0.2917 0.4491 0.032 Uiso 1 calc . . GR C7 C 0.2955(5) 0.3068(3) 0.7796(5) 0.0270(13) Uani 1 d . . . H7A H 0.3498 0.2890 0.8433 0.041 Uiso 1 calc . . GR H7B H 0.2378 0.3350 0.8033 0.041 Uiso 1 calc . . GR H7C H 0.3305 0.3408 0.7360 0.041 Uiso 1 calc . . GR C8 C 0.2488(5) 0.1368(4) 0.8685(5) 0.0255(13) Uani 1 d . . . H8A H 0.2569 0.0806 0.8735 0.038 Uiso 1 calc . . GR H8B H 0.1887 0.1528 0.9006 0.038 Uiso 1 calc . . GR H8C H 0.3165 0.1613 0.9077 0.038 Uiso 1 calc . . GR C9 C 0.1301(5) 0.0305(3) 0.6592(5) 0.0225(12) Uani 1 d . . . H9A H 0.1565 -0.0019 0.6073 0.034 Uiso 1 calc . . GR H9B H 0.0502 0.0317 0.6399 0.034 Uiso 1 calc . . GR H9C H 0.1552 0.0093 0.7325 0.034 Uiso 1 calc . . GR C10 C 0.1112(5) 0.1356(3) 0.4420(5) 0.0222(13) Uani 1 d . . . H10A H 0.1020 0.1818 0.3946 0.027 Uiso 1 calc . . R H10B H 0.0378 0.1144 0.4392 0.027 Uiso 1 calc . . R C11 C 0.1780(5) 0.0743(3) 0.3946(5) 0.0235(13) Uani 1 d . . . H11A H 0.1812 0.0263 0.4376 0.028 Uiso 1 calc . . R H11B H 0.1387 0.0624 0.3193 0.028 Uiso 1 calc . . R C12 C 0.2957(5) 0.0990(4) 0.3938(5) 0.0253(13) Uani 1 d . . . H12A H 0.3217 0.0683 0.3388 0.030 Uiso 1 calc . . R H12B H 0.2958 0.1540 0.3728 0.030 Uiso 1 calc . . R C13 C 0.4317(5) 0.0102(3) 0.7821(4) 0.0208(12) Uani 1 d . . . H13 H 0.3581 -0.0065 0.7678 0.025 Uiso 1 calc . . R C14 C 0.5118(5) -0.0351(3) 0.8491(5) 0.0296(14) Uani 1 d . . . H14 H 0.4923 -0.0809 0.8811 0.036 Uiso 1 calc . . R C15 C 0.6229(5) -0.0117(3) 0.8688(5) 0.0242(13) Uani 1 d . . . H15 H 0.6783 -0.0410 0.9152 0.029 Uiso 1 calc . . R C16 C 0.6489(4) 0.0551(3) 0.8186(4) 0.0200(12) Uani 1 d . . . H16 H 0.7227 0.0706 0.8280 0.024 Uiso 1 calc . . R C17 C 0.5636(4) 0.1001(3) 0.7529(4) 0.0168(11) Uani 1 d . . . C18 C 0.5813(4) 0.1755(3) 0.7015(4) 0.0149(11) Uani 1 d . . . C19 C 0.6842(4) 0.2098(3) 0.7087(4) 0.0183(12) Uani 1 d . . . H19 H 0.7483 0.1850 0.7480 0.022 Uiso 1 calc . . R C20 C 0.6912(5) 0.2808(3) 0.6575(4) 0.0226(13) Uani 1 d . . . H20 H 0.7598 0.3047 0.6620 0.027 Uiso 1 calc . . R C21 C 0.5944(4) 0.3164(3) 0.5989(4) 0.0194(12) Uani 1 d . . . H21 H 0.5973 0.3645 0.5639 0.023 Uiso 1 calc . . R C22 C 0.4940(4) 0.2798(3) 0.5932(4) 0.0191(12) Uani 1 d . . . H22 H 0.4295 0.3036 0.5530 0.023 Uiso 1 calc . . R Cl1 Cl -0.06150(11) 0.09585(9) 0.83581(12) 0.0274(3) Uani 1 d . . . Cl2 Cl 0.37516(11) -0.09934(8) 0.54129(11) 0.0239(3) Uani 1 d . . . O1 O -0.1204(3) 0.1267(3) 0.5668(4) 0.0325(10) Uani 1 d . . . O2 O 0.4503(4) 0.2166(3) 1.0760(4) 0.0389(11) Uani 1 d . . . O3 O 0.1262(3) -0.0310(3) 0.9448(4) 0.0399(12) Uani 1 d . . . O4 O 0.4717(4) 0.2216(3) 0.3033(4) 0.0442(12) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01327(14) 0.01384(14) 0.01268(13) 0.00028(7) 0.00389(9) -0.00026(8) N1 0.020(2) 0.019(2) 0.021(2) -0.0019(19) 0.0086(19) 0.000(2) C1 0.013(3) 0.025(3) 0.021(3) -0.001(2) 0.007(2) -0.002(2) N2 0.021(2) 0.013(2) 0.013(2) -0.0031(17) 0.0031(18) 0.0009(19) C2 0.016(3) 0.020(3) 0.016(3) 0.000(2) 0.006(2) 0.000(2) N3 0.015(2) 0.018(2) 0.011(2) -0.0036(17) 0.0044(17) 0.0025(19) C3 0.015(3) 0.023(3) 0.020(3) -0.002(2) 0.013(2) -0.002(2) C4 0.014(3) 0.016(3) 0.022(3) 0.000(2) 0.006(2) 0.001(2) C5 0.012(3) 0.021(3) 0.015(3) 0.002(2) 0.003(2) 0.001(2) C6 0.022(3) 0.015(3) 0.029(3) 0.003(2) 0.008(2) 0.001(2) C7 0.033(3) 0.023(3) 0.027(3) -0.009(2) 0.012(3) -0.004(3) C8 0.028(3) 0.033(3) 0.019(3) 0.008(2) 0.011(2) -0.001(3) C9 0.026(3) 0.014(3) 0.028(3) 0.003(2) 0.009(2) -0.004(2) C10 0.020(3) 0.025(3) 0.019(3) 0.003(2) -0.002(2) -0.002(2) C11 0.032(3) 0.023(3) 0.014(3) -0.003(2) 0.003(2) 0.003(3) C12 0.028(3) 0.030(3) 0.016(3) -0.006(2) 0.001(2) 0.001(3) C13 0.028(3) 0.016(3) 0.019(3) 0.004(2) 0.008(2) -0.001(2) C14 0.042(4) 0.019(3) 0.027(3) 0.003(2) 0.005(3) 0.004(3) C15 0.028(3) 0.023(3) 0.020(3) 0.004(2) 0.002(2) 0.007(3) C16 0.018(3) 0.026(3) 0.016(3) -0.003(2) 0.003(2) 0.007(2) C17 0.017(3) 0.020(3) 0.013(2) -0.004(2) 0.004(2) 0.001(2) C18 0.017(3) 0.016(3) 0.012(2) -0.003(2) 0.004(2) 0.004(2) C19 0.012(3) 0.023(3) 0.019(3) 0.002(2) 0.001(2) 0.003(2) C20 0.018(3) 0.032(3) 0.019(3) -0.004(2) 0.006(2) -0.008(3) C21 0.025(3) 0.012(3) 0.023(3) 0.001(2) 0.009(2) 0.001(2) C22 0.019(3) 0.020(3) 0.020(3) 0.002(2) 0.008(2) -0.002(2) Cl1 0.0206(7) 0.0339(8) 0.0264(7) 0.0036(6) 0.0028(6) 0.0029(6) Cl2 0.0252(7) 0.0231(7) 0.0246(7) -0.0018(5) 0.0082(6) -0.0017(6) O1 0.031(2) 0.034(2) 0.033(2) -0.003(2) 0.0097(19) 0.002(2) O2 0.032(2) 0.031(3) 0.053(3) -0.009(2) 0.010(2) -0.001(2) O3 0.028(2) 0.041(3) 0.056(3) 0.021(2) 0.021(2) 0.012(2) O4 0.045(3) 0.035(3) 0.048(3) 0.010(2) 0.000(2) -0.003(2) _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 N1 2.112(4) . ? Ir1 C1 2.166(5) . ? Ir1 N2 2.083(4) . ? Ir1 C2 2.173(5) . ? Ir1 N3 2.090(4) . ? Ir1 C3 2.183(5) . ? Ir1 C4 2.160(5) . ? Ir1 C5 2.169(5) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N1 C12 1.482(7) . ? C1 C2 1.453(7) . ? C1 C5 1.433(7) . ? C1 C6 1.499(7) . ? N2 C13 1.349(7) . ? N2 C17 1.352(7) . ? C2 C3 1.426(7) . ? C2 C7 1.501(7) . ? N3 C18 1.362(6) . ? N3 C22 1.359(7) . ? C3 C4 1.444(7) . ? C3 C8 1.486(8) . ? C4 C5 1.441(7) . ? C4 C9 1.505(7) . ? C5 C10 1.497(7) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.528(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.516(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13 0.9300 . ? C13 C14 1.372(8) . ? C14 H14 0.9300 . ? C14 C15 1.395(9) . ? C15 H15 0.9300 . ? C15 C16 1.368(8) . ? C16 H16 0.9300 . ? C16 C17 1.400(7) . ? C17 C18 1.471(8) . ? C18 C19 1.382(7) . ? C19 H19 0.9300 . ? C19 C20 1.376(8) . ? C20 H20 0.9300 . ? C20 C21 1.386(8) . ? C21 H21 0.9300 . ? C21 C22 1.374(8) . ? C22 H22 0.9300 . ? 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 N1 Ir1 C1 114.53(18) . . ? N1 Ir1 C2 153.67(18) . . ? N1 Ir1 C3 145.98(19) . . ? N1 Ir1 C4 107.92(19) . . ? N1 Ir1 C5 93.25(19) . . ? C1 Ir1 C2 39.13(19) . . ? C1 Ir1 C3 64.6(2) . . ? C1 Ir1 C5 38.61(19) . . ? N2 Ir1 N1 85.17(17) . . ? N2 Ir1 C1 160.18(19) . . ? N2 Ir1 C2 121.13(18) . . ? N2 Ir1 N3 76.34(17) . . ? N2 Ir1 C3 98.15(19) . . ? N2 Ir1 C4 108.26(18) . . ? N2 Ir1 C5 144.48(18) . . ? C2 Ir1 C3 38.22(19) . . ? N3 Ir1 N1 85.64(17) . . ? N3 Ir1 C1 105.91(18) . . ? N3 Ir1 C2 100.89(17) . . ? N3 Ir1 C3 128.16(18) . . ? N3 Ir1 C4 165.80(18) . . ? N3 Ir1 C5 139.03(18) . . ? C4 Ir1 C1 65.12(19) . . ? C4 Ir1 C2 65.09(19) . . ? C4 Ir1 C3 38.8(2) . . ? C4 Ir1 C5 38.9(2) . . ? C5 Ir1 C2 65.05(19) . . ? C5 Ir1 C3 64.7(2) . . ? Ir1 N1 H1A 108.1 . . ? Ir1 N1 H1B 108.1 . . ? H1A N1 H1B 107.3 . . ? C12 N1 Ir1 116.8(3) . . ? C12 N1 H1A 108.1 . . ? C12 N1 H1B 108.1 . . ? C2 C1 Ir1 70.7(3) . . ? C2 C1 C6 126.4(5) . . ? C5 C1 Ir1 70.8(3) . . ? C5 C1 C2 108.0(5) . . ? C5 C1 C6 125.2(5) . . ? C6 C1 Ir1 129.6(4) . . ? C13 N2 Ir1 123.7(4) . . ? C13 N2 C17 118.5(4) . . ? C17 N2 Ir1 117.8(3) . . ? C1 C2 Ir1 70.2(3) . . ? C1 C2 C7 125.0(5) . . ? C3 C2 Ir1 71.3(3) . . ? C3 C2 C1 107.7(5) . . ? C3 C2 C7 127.3(5) . . ? C7 C2 Ir1 126.3(4) . . ? C18 N3 Ir1 117.6(3) . . ? C22 N3 Ir1 124.6(3) . . ? C22 N3 C18 117.8(4) . . ? C2 C3 Ir1 70.5(3) . . ? C2 C3 C4 108.6(5) . . ? C2 C3 C8 125.1(5) . . ? C4 C3 Ir1 69.7(3) . . ? C4 C3 C8 126.3(5) . . ? C8 C3 Ir1 126.5(4) . . ? C3 C4 Ir1 71.4(3) . . ? C3 C4 C9 126.7(5) . . ? C5 C4 Ir1 70.9(3) . . ? C5 C4 C3 107.5(5) . . ? C5 C4 C9 125.3(5) . . ? C9 C4 Ir1 128.9(4) . . ? C1 C5 Ir1 70.6(3) . . ? C1 C5 C4 108.2(5) . . ? C1 C5 C10 125.7(5) . . ? C4 C5 Ir1 70.2(3) . . ? C4 C5 C10 126.1(5) . . ? C10 C5 Ir1 124.1(4) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 108.4 . . ? C5 C10 H10B 108.4 . . ? C5 C10 C11 115.4(4) . . ? H10A C10 H10B 107.5 . . ? C11 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C10 C11 H11A 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C12 C11 C10 114.7(5) . . ? C12 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? N1 C12 C11 112.0(5) . . ? N1 C12 H12A 109.2 . . ? N1 C12 H12B 109.2 . . ? C11 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? N2 C13 H13 118.8 . . ? N2 C13 C14 122.4(5) . . ? C14 C13 H13 118.8 . . ? C13 C14 H14 120.3 . . ? C13 C14 C15 119.3(6) . . ? C15 C14 H14 120.3 . . ? C14 C15 H15 120.6 . . ? C16 C15 C14 118.8(5) . . ? C16 C15 H15 120.6 . . ? C15 C16 H16 120.2 . . ? C15 C16 C17 119.5(5) . . ? C17 C16 H16 120.2 . . ? N2 C17 C16 121.4(5) . . ? N2 C17 C18 114.4(4) . . ? C16 C17 C18 124.1(5) . . ? N3 C18 C17 113.7(4) . . ? N3 C18 C19 121.9(5) . . ? C19 C18 C17 124.4(5) . . ? C18 C19 H19 120.2 . . ? C20 C19 C18 119.6(5) . . ? C20 C19 H19 120.2 . . ? C19 C20 H20 120.5 . . ? C19 C20 C21 119.1(5) . . ? C21 C20 H20 120.5 . . ? C20 C21 H21 120.4 . . ? C22 C21 C20 119.2(5) . . ? C22 C21 H21 120.4 . . ? N3 C22 C21 122.4(5) . . ? N3 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Ir1 N1 C12 C11 -59.8(6) . . . . ? Ir1 C1 C2 C3 -61.8(4) . . . . ? Ir1 C1 C2 C7 121.0(5) . . . . ? Ir1 C1 C5 C4 60.4(4) . . . . ? Ir1 C1 C5 C10 -118.6(6) . . . . ? Ir1 N2 C13 C14 -178.2(4) . . . . ? Ir1 N2 C17 C16 179.6(4) . . . . ? Ir1 N2 C17 C18 2.5(6) . . . . ? Ir1 C2 C3 C4 -59.5(4) . . . . ? Ir1 C2 C3 C8 121.5(6) . . . . ? Ir1 N3 C18 C17 -0.8(6) . . . . ? Ir1 N3 C18 C19 178.9(4) . . . . ? Ir1 N3 C22 C21 -179.4(4) . . . . ? Ir1 C3 C4 C5 -62.1(4) . . . . ? Ir1 C3 C4 C9 125.1(5) . . . . ? Ir1 C4 C5 C1 -60.7(4) . . . . ? Ir1 C4 C5 C10 118.3(6) . . . . ? Ir1 C5 C10 C11 22.1(7) . . . . ? N1 Ir1 C1 C2 179.7(3) . . . . ? N1 Ir1 C1 C5 61.8(3) . . . . ? N1 Ir1 C1 C6 -58.5(5) . . . . ? N1 Ir1 N2 C13 -94.1(4) . . . . ? N1 Ir1 N2 C17 84.5(4) . . . . ? N1 Ir1 C2 C1 -0.5(6) . . . . ? N1 Ir1 C2 C3 117.0(4) . . . . ? N1 Ir1 C2 C7 -120.0(5) . . . . ? N1 Ir1 N3 C18 -84.5(4) . . . . ? N1 Ir1 N3 C22 94.3(4) . . . . ? N1 Ir1 C3 C2 -135.1(3) . . . . ? N1 Ir1 C3 C4 -15.6(5) . . . . ? N1 Ir1 C3 C8 105.1(5) . . . . ? N1 Ir1 C4 C3 170.9(3) . . . . ? N1 Ir1 C4 C5 -72.2(3) . . . . ? N1 Ir1 C4 C9 48.3(5) . . . . ? N1 Ir1 C5 C1 -126.5(3) . . . . ? N1 Ir1 C5 C4 114.9(3) . . . . ? N1 Ir1 C5 C10 -6.0(5) . . . . ? C1 Ir1 N1 C12 -9.9(4) . . . . ? C1 Ir1 N2 C13 80.1(7) . . . . ? C1 Ir1 N2 C17 -101.3(6) . . . . ? C1 Ir1 C2 C3 117.6(4) . . . . ? C1 Ir1 C2 C7 -119.5(6) . . . . ? C1 Ir1 N3 C18 161.2(4) . . . . ? C1 Ir1 N3 C22 -20.0(5) . . . . ? C1 Ir1 C3 C2 -38.3(3) . . . . ? C1 Ir1 C3 C4 81.2(3) . . . . ? C1 Ir1 C3 C8 -158.1(5) . . . . ? C1 Ir1 C4 C3 -79.8(3) . . . . ? C1 Ir1 C4 C5 37.2(3) . . . . ? C1 Ir1 C4 C9 157.6(5) . . . . ? C1 Ir1 C5 C4 -118.6(4) . . . . ? C1 Ir1 C5 C10 120.6(6) . . . . ? C1 C2 C3 Ir1 61.1(4) . . . . ? C1 C2 C3 C4 1.5(6) . . . . ? C1 C2 C3 C8 -177.4(5) . . . . ? C1 C5 C10 C11 111.6(6) . . . . ? N2 Ir1 N1 C12 168.0(4) . . . . ? N2 Ir1 C1 C2 6.0(7) . . . . ? N2 Ir1 C1 C5 -111.9(6) . . . . ? N2 Ir1 C1 C6 127.8(6) . . . . ? N2 Ir1 C2 C1 -177.6(3) . . . . ? N2 Ir1 C2 C3 -60.1(3) . . . . ? N2 Ir1 C2 C7 62.9(5) . . . . ? N2 Ir1 N3 C18 1.6(3) . . . . ? N2 Ir1 N3 C22 -179.6(4) . . . . ? N2 Ir1 C3 C2 131.5(3) . . . . ? N2 Ir1 C3 C4 -109.1(3) . . . . ? N2 Ir1 C3 C8 11.6(5) . . . . ? N2 Ir1 C4 C3 80.1(3) . . . . ? N2 Ir1 C4 C5 -163.0(3) . . . . ? N2 Ir1 C4 C9 -42.5(5) . . . . ? N2 Ir1 C5 C1 147.2(3) . . . . ? N2 Ir1 C5 C4 28.6(5) . . . . ? N2 Ir1 C5 C10 -92.2(5) . . . . ? N2 C13 C14 C15 -1.7(9) . . . . ? N2 C17 C18 N3 -1.1(7) . . . . ? N2 C17 C18 C19 179.2(5) . . . . ? C2 Ir1 N1 C12 -9.5(7) . . . . ? C2 Ir1 C1 C5 -117.9(4) . . . . ? C2 Ir1 C1 C6 121.7(6) . . . . ? C2 Ir1 N2 C13 84.6(4) . . . . ? C2 Ir1 N2 C17 -96.8(4) . . . . ? C2 Ir1 N3 C18 121.2(4) . . . . ? C2 Ir1 N3 C22 -60.0(4) . . . . ? C2 Ir1 C3 C4 119.5(4) . . . . ? C2 Ir1 C3 C8 -119.8(6) . . . . ? C2 Ir1 C4 C3 -36.4(3) . . . . ? C2 Ir1 C4 C5 80.5(3) . . . . ? C2 Ir1 C4 C9 -159.1(5) . . . . ? C2 Ir1 C5 C1 38.0(3) . . . . ? C2 Ir1 C5 C4 -80.6(3) . . . . ? C2 Ir1 C5 C10 158.5(5) . . . . ? C2 C1 C5 Ir1 -61.3(4) . . . . ? C2 C1 C5 C4 -0.8(6) . . . . ? C2 C1 C5 C10 -179.8(5) . . . . ? C2 C3 C4 Ir1 60.0(4) . . . . ? C2 C3 C4 C5 -2.0(6) . . . . ? C2 C3 C4 C9 -174.9(5) . . . . ? N3 Ir1 N1 C12 -115.4(4) . . . . ? N3 Ir1 C1 C2 -87.8(3) . . . . ? N3 Ir1 C1 C5 154.3(3) . . . . ? N3 Ir1 C1 C6 34.0(5) . . . . ? N3 Ir1 N2 C13 179.2(4) . . . . ? N3 Ir1 N2 C17 -2.2(4) . . . . ? N3 Ir1 C2 C1 101.9(3) . . . . ? N3 Ir1 C2 C3 -140.6(3) . . . . ? N3 Ir1 C2 C7 -17.6(5) . . . . ? N3 Ir1 C3 C2 52.5(4) . . . . ? N3 Ir1 C3 C4 171.9(3) . . . . ? N3 Ir1 C3 C8 -67.4(5) . . . . ? N3 Ir1 C4 C3 -26.8(9) . . . . ? N3 Ir1 C4 C5 90.2(8) . . . . ? N3 Ir1 C4 C9 -149.4(6) . . . . ? N3 Ir1 C5 C1 -39.5(4) . . . . ? N3 Ir1 C5 C4 -158.0(3) . . . . ? N3 Ir1 C5 C10 81.1(5) . . . . ? N3 C18 C19 C20 0.4(8) . . . . ? C3 Ir1 N1 C12 70.5(5) . . . . ? C3 Ir1 C1 C2 37.4(3) . . . . ? C3 Ir1 C1 C5 -80.5(3) . . . . ? C3 Ir1 C1 C6 159.1(5) . . . . ? C3 Ir1 N2 C13 51.8(4) . . . . ? C3 Ir1 N2 C17 -129.6(4) . . . . ? C3 Ir1 C2 C1 -117.6(4) . . . . ? C3 Ir1 C2 C7 123.0(6) . . . . ? C3 Ir1 N3 C18 91.3(4) . . . . ? C3 Ir1 N3 C22 -89.9(5) . . . . ? C3 Ir1 C4 C5 116.9(4) . . . . ? C3 Ir1 C4 C9 -122.6(6) . . . . ? C3 Ir1 C5 C1 80.4(3) . . . . ? C3 Ir1 C5 C4 -38.2(3) . . . . ? C3 Ir1 C5 C10 -159.1(5) . . . . ? C3 C4 C5 Ir1 62.4(4) . . . . ? C3 C4 C5 C1 1.8(6) . . . . ? C3 C4 C5 C10 -179.2(5) . . . . ? C4 Ir1 N1 C12 60.3(4) . . . . ? C4 Ir1 C1 C2 80.5(3) . . . . ? C4 Ir1 C1 C5 -37.4(3) . . . . ? C4 Ir1 C1 C6 -157.8(5) . . . . ? C4 Ir1 N2 C13 13.2(5) . . . . ? C4 Ir1 N2 C17 -168.2(4) . . . . ? C4 Ir1 C2 C1 -80.5(3) . . . . ? C4 Ir1 C2 C3 37.0(3) . . . . ? C4 Ir1 C2 C7 160.0(5) . . . . ? C4 Ir1 N3 C18 112.3(7) . . . . ? C4 Ir1 N3 C22 -68.9(9) . . . . ? C4 Ir1 C3 C2 -119.5(4) . . . . ? C4 Ir1 C3 C8 120.7(6) . . . . ? C4 Ir1 C5 C1 118.6(4) . . . . ? C4 Ir1 C5 C10 -120.8(6) . . . . ? C4 C5 C10 C11 -67.2(7) . . . . ? C5 Ir1 N1 C12 23.5(4) . . . . ? C5 Ir1 C1 C2 117.9(4) . . . . ? C5 Ir1 C1 C6 -120.3(6) . . . . ? C5 Ir1 N2 C13 -5.3(6) . . . . ? C5 Ir1 N2 C17 173.3(4) . . . . ? C5 Ir1 C2 C1 -37.5(3) . . . . ? C5 Ir1 C2 C3 80.1(3) . . . . ? C5 Ir1 C2 C7 -156.9(5) . . . . ? C5 Ir1 N3 C18 -174.5(3) . . . . ? C5 Ir1 N3 C22 4.4(6) . . . . ? C5 Ir1 C3 C2 -81.2(3) . . . . ? C5 Ir1 C3 C4 38.3(3) . . . . ? C5 Ir1 C3 C8 159.0(5) . . . . ? C5 Ir1 C4 C3 -116.9(4) . . . . ? C5 Ir1 C4 C9 120.4(6) . . . . ? C5 C1 C2 Ir1 61.3(4) . . . . ? C5 C1 C2 C3 -0.4(6) . . . . ? C5 C1 C2 C7 -177.6(5) . . . . ? C5 C10 C11 C12 -58.0(7) . . . . ? C6 C1 C2 Ir1 -125.5(5) . . . . ? C6 C1 C2 C3 172.7(5) . . . . ? C6 C1 C2 C7 -4.5(8) . . . . ? C6 C1 C5 Ir1 125.5(5) . . . . ? C6 C1 C5 C4 -174.1(5) . . . . ? C6 C1 C5 C10 6.9(9) . . . . ? C7 C2 C3 Ir1 -121.8(5) . . . . ? C7 C2 C3 C4 178.7(5) . . . . ? C7 C2 C3 C8 -0.3(9) . . . . ? C8 C3 C4 Ir1 -121.0(6) . . . . ? C8 C3 C4 C5 176.9(5) . . . . ? C8 C3 C4 C9 4.1(9) . . . . ? C9 C4 C5 Ir1 -124.6(5) . . . . ? C9 C4 C5 C1 174.7(5) . . . . ? C9 C4 C5 C10 -6.3(9) . . . . ? C10 C11 C12 N1 81.0(6) . . . . ? C13 N2 C17 C16 -1.8(7) . . . . ? C13 N2 C17 C18 -178.9(5) . . . . ? C13 C14 C15 C16 -1.4(9) . . . . ? C14 C15 C16 C17 2.7(8) . . . . ? C15 C16 C17 N2 -1.2(8) . . . . ? C15 C16 C17 C18 175.6(5) . . . . ? C16 C17 C18 N3 -178.1(5) . . . . ? C16 C17 C18 C19 2.2(9) . . . . ? C17 N2 C13 C14 3.2(8) . . . . ? C17 C18 C19 C20 -179.9(5) . . . . ? C18 N3 C22 C21 -0.6(8) . . . . ? C18 C19 C20 C21 -0.3(8) . . . . ? C19 C20 C21 C22 -0.3(8) . . . . ? C20 C21 C22 N3 0.8(8) . . . . ? C22 N3 C18 C17 -179.7(5) . . . . ? C22 N3 C18 C19 0.0(7) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 1 16 13 0.0565 1.0005 16.0019 12.9996 0.4708 -0.8683 0.2806 6 -15 11 0.0795 6.0000 -15.0002 11.0000 0.3321 0.2844 0.9210 -6 15 -11 0.0795 -6.0000 15.0002 -11.0000 -0.3321 -0.2844 -0.9210 0 -6 17 0.0558 0.0004 -5.9988 16.9997 0.7377 -0.0718 0.7150 0 6 -17 0.0558 -0.0004 5.9988 -16.9997 -0.7377 0.0718 -0.7150 8 9 -16 0.0706 7.9995 8.9986 -15.9996 -0.9438 -0.1947 -0.3392 16 8 -2 0.1115 15.9997 7.9992 -1.9998 -0.5877 -0.5390 0.5745 -3 -19 -10 0.0469 -3.0004 -19.0017 -9.9997 -0.2749 0.9639 -0.2211 15 -11 -2 0.1087 14.9995 -11.0017 -1.9996 -0.4993 0.2129 0.8163 -15 13 3 0.1122 -14.9995 13.0019 2.9996 0.5354 -0.3082 -0.8102 1 -19 10 0.0620 1.0000 -19.0002 10.0000 0.4517 0.5399 0.7048 -1 19 -10 0.0620 -1.0000 19.0002 -10.0000 -0.4517 -0.5399 -0.7048 -17 0 9 0.1023 -16.9994 0.0019 8.9995 0.8891 0.1208 -0.4880 17 0 -9 0.1023 16.9994 -0.0019 -8.9995 -0.8891 -0.1208 0.4880 -9 7 16 0.0723 -8.9993 7.0023 15.9995 0.9245 -0.4079 0.0468 -2 -4 -16 0.0440 -2.0005 -4.0015 -15.9997 -0.6048 0.4741 -0.6219 12 -4 -15 0.0710 11.9993 -4.0023 -14.9995 -0.9811 0.2242 0.0884 _olex2_submission_special_instructions 'No special instructions were received'