#------------------------------------------------------------------------------ #$Date: 2020-06-05 12:31:21 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252670 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557984.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557984 loop_ _publ_author_name 'Gonz\'alez-Lainez, Miguel' 'Jim\'enez, M. Victoria' 'Passarelli, Vincenzo' 'P\'erez-Torrente, Jes\'us J.' _publ_section_title ; Effective N-methylation of nitroarenes with methanol catalyzed by a functionalized NHC-based iridium catalyst: a green approach to N-methyl amines ; _journal_issue 10 _journal_name_full 'Catalysis Science & Technology' _journal_page_first 3458 _journal_paper_doi 10.1039/D0CY00707B _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C17 H21 Br Ir N3 O3' _chemical_formula_sum 'C17 H21 Br Ir N3 O3' _chemical_formula_weight 587.48 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-07-23 deposited with the CCDC. 2020-05-01 downloaded from the CCDC. ; _cell_angle_alpha 99.1570(10) _cell_angle_beta 110.946(2) _cell_angle_gamma 114.3940(10) _cell_formula_units_Z 2 _cell_length_a 9.2294(9) _cell_length_b 11.1211(11) _cell_length_c 11.8920(19) _cell_measurement_reflns_used 7571 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.267 _cell_measurement_theta_min 2.335 _cell_volume 968.3(2) _computing_cell_refinement 'SAINT+ in APEX2 (Bruker AXS,2008)' _computing_data_collection 'SMART in APEX2 (Bruker AXS,2008)' _computing_data_reduction 'SAINT+ in APEX2 (Bruker AXS,2008)' _computing_molecular_graphics 'XP program, SHELXTL v6.12, Bruker2000' _computing_publication_material 'XCIF program, PLATON(Spek, 1998)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-2013 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 8.26 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX DUO system' _diffrn_measurement_method '\w and \f rotations with narrow frames' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_unetI/netI 0.0220 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 11641 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 26.368 _diffrn_reflns_theta_min 1.966 _exptl_absorpt_coefficient_mu 8.978 _exptl_absorpt_correction_T_max 0.1695 _exptl_absorpt_correction_T_min 0.1208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Multi-scan correction included in APEX2 package (Bruker AXS, 2008) ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.015 _exptl_crystal_description prism _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.180 _refine_diff_density_max 2.507 _refine_diff_density_min -2.000 _refine_diff_density_rms 0.137 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 3938 _refine_ls_number_restraints 31 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0290 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+5.1495P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.0740 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3700 _reflns_number_total 3938 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cy00707b2.cif _cod_data_source_block cmpd_4_VPX142 _cod_depositor_comments 'Adding full bibliography for 1557983--1557984.cif.' _cod_database_code 1557984 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL p1 in P-1 CELL 0.71073 9.2294 11.1211 11.8920 99.157 110.946 114.394 ZERR 2.00 0.0009 0.0011 0.0019 0.001 0.002 0.001 LATT 1 SFAC C H N O BR IR UNIT 34 42 6 6 2 2 MERG 2 SADI N5 C6a N5 C6b SADI C6a C7a C6a C8a C6a C9a C6b C7b C6b C8b C6b C9b SADI C7a C8a C7a C9a C8a C9a C7b C8B C7B C9B C8B C9B SHEL 9999 0.80 FMAP 2 PLAN 10 ACTA 50.00 BOND $H L.S. 6 TEMP -173.00 WGHT 0.031100 5.149500 FVAR 0.11804 0.40139 PART 1 C6A 1 0.912012 -0.330534 0.653733 21.00000 0.02715 C7A 1 0.709123 -0.424102 0.607697 21.00000 0.04338 AFIX 137 H7A1 2 0.687715 -0.423841 0.682706 21.00000 -1.50000 H7A2 2 0.667240 -0.521132 0.556812 21.00000 -1.50000 H7A3 2 0.643128 -0.386956 0.554237 21.00000 -1.50000 AFIX 0 C8A 1 0.940834 -0.319140 0.537723 21.00000 0.05648 AFIX 137 H8A1 2 0.867507 -0.284214 0.488229 21.00000 -1.50000 H8A2 2 0.905237 -0.412581 0.483091 21.00000 -1.50000 H8A3 2 1.068463 -0.253229 0.566561 21.00000 -1.50000 AFIX 0 C9A 1 1.006789 -0.401551 0.723610 21.00000 0.02453 AFIX 137 H9A1 2 1.131388 -0.356117 0.737796 21.00000 -1.50000 H9A2 2 0.942989 -0.502157 0.670858 21.00000 -1.50000 H9A3 2 1.006719 -0.391881 0.806950 21.00000 -1.50000 AFIX 0 PART 2 C6B 1 0.882547 -0.340443 0.660747 -21.00000 0.02918 C7B 1 0.725168 -0.431916 0.679340 -21.00000 0.04728 AFIX 137 H7B1 2 0.765603 -0.415977 0.771386 -21.00000 -1.50000 H7B2 2 0.676241 -0.531741 0.631653 -21.00000 -1.50000 H7B3 2 0.631388 -0.407473 0.647064 -21.00000 -1.50000 AFIX 0 C8B 1 0.819190 -0.353580 0.519413 -21.00000 0.04443 AFIX 137 H8B1 2 0.719149 -0.335434 0.490577 -21.00000 -1.50000 H8B2 2 0.778689 -0.449317 0.466333 -21.00000 -1.50000 H8B3 2 0.919114 -0.284412 0.510720 -21.00000 -1.50000 AFIX 0 C9B 1 1.022963 -0.386887 0.695938 -21.00000 0.06146 AFIX 137 H9B1 2 1.118021 -0.332020 0.675382 -21.00000 -1.50000 H9B2 2 0.964619 -0.487834 0.646455 -21.00000 -1.50000 H9B3 2 1.075912 -0.370464 0.788448 -21.00000 -1.50000 AFIX 0 PART 0 C1 1 0.894197 -0.107780 0.730081 11.00000 0.03099 0.02319 = 0.02501 0.00662 0.01358 0.00956 C4 1 1.161618 0.011301 0.912010 11.00000 0.03159 0.03426 = 0.02577 0.00771 0.00646 0.00260 AFIX 43 H4 2 1.262059 0.084282 0.990001 11.00000 -1.20000 AFIX 0 C3 1 1.137468 -0.115262 0.857570 11.00000 0.02496 0.03562 = 0.02930 0.01322 0.00351 0.00790 AFIX 43 H3 2 1.217665 -0.148727 0.889591 11.00000 -1.20000 AFIX 0 C10 1 0.982507 0.132780 0.863888 11.00000 0.03328 0.02823 = 0.03568 0.00200 0.01962 0.00678 AFIX 23 H10A 2 0.981335 0.145952 0.947811 11.00000 -1.20000 H10B 2 0.862034 0.106930 0.797288 11.00000 -1.20000 AFIX 0 C11 1 1.120933 0.271076 0.870851 11.00000 0.02485 0.02776 = 0.02557 0.00688 0.01001 0.01084 C13 1 1.262130 0.512569 0.961180 11.00000 0.02468 0.03277 = 0.02654 0.01080 0.00725 0.01702 C14 1 1.353149 0.531637 0.888453 11.00000 0.02988 0.03246 = 0.03206 0.02024 0.01365 0.01653 AFIX 43 H14 2 1.433244 0.623898 0.896189 11.00000 -1.20000 AFIX 0 C15 1 1.323980 0.412356 0.804210 11.00000 0.03326 0.04333 = 0.03025 0.02107 0.01820 0.02466 AFIX 43 H15 2 1.384419 0.421588 0.753283 11.00000 -1.20000 AFIX 0 C16 1 1.205760 0.279800 0.795314 11.00000 0.03222 0.03424 = 0.02336 0.00798 0.01272 0.01740 AFIX 43 H16 2 1.183564 0.196571 0.738320 11.00000 -1.20000 AFIX 0 C17 1 1.289229 0.635167 1.057789 11.00000 0.03459 0.03026 = 0.03812 0.01055 0.01611 0.01817 AFIX 23 H17A 2 1.170771 0.620765 1.046134 11.00000 -1.20000 H17B 2 1.357961 0.641311 1.146362 11.00000 -1.20000 AFIX 0 C19 1 1.443985 0.883459 1.144079 11.00000 0.03346 0.03099 = 0.04844 0.00152 0.01270 0.01459 AFIX 137 H19A 2 1.339776 0.879274 1.151538 11.00000 -1.50000 H19B 2 1.505763 0.969163 1.127751 11.00000 -1.50000 H19C 2 1.527276 0.885504 1.224581 11.00000 -1.50000 AFIX 0 C20 1 0.758351 -0.064411 0.495779 11.00000 0.03155 0.04215 = 0.02976 0.00444 0.00020 0.02536 C22 1 0.419302 -0.184717 0.470140 11.00000 0.03654 0.02416 = 0.05021 0.01231 0.01479 0.01475 N5 3 1.013350 0.015715 0.833594 11.00000 0.03153 0.02324 = 0.03010 0.00569 0.01622 0.00652 N2 3 0.972637 -0.188422 0.745222 11.00000 0.02768 0.02560 = 0.02499 0.00682 0.00849 0.00873 N12 3 1.147647 0.385154 0.953518 11.00000 0.02430 0.02872 = 0.02469 0.00569 0.01027 0.01280 O18 4 1.385056 0.762945 1.040771 11.00000 0.05249 0.02488 = 0.04622 0.01080 0.02225 0.01745 O21 4 0.820588 -0.014297 0.442405 11.00000 0.04102 0.06070 = 0.04192 0.02426 0.01963 0.02884 O23 4 0.281253 -0.212617 0.396342 11.00000 0.03317 0.03961 = 0.07429 0.01903 0.00567 0.01793 BR 5 0.510796 -0.230748 0.727002 11.00000 0.04502 0.03622 = 0.04758 0.01191 0.02475 0.00994 IR 6 0.649279 -0.144761 0.591725 11.00000 0.02744 0.02133 = 0.03095 0.00564 0.01044 0.01066 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM p1 in P-1 REM R1 = 0.0290 for 3700 Fo > 4sig(Fo) and 0.0313 for all 3938 data REM 230 parameters refined using 31 restraints END WGHT 0.0311 5.1495 REM Highest difference peak 2.507, deepest hole -2.000, 1-sigma level 0.137 Q1 1 0.7047 -0.1450 0.6615 11.00000 0.05 2.51 Q2 1 0.6742 -0.0641 0.6249 11.00000 0.05 1.29 Q3 1 0.6044 -0.2306 0.5442 11.00000 0.05 0.92 Q4 1 0.5852 -0.2590 0.7734 11.00000 0.05 0.88 Q5 1 0.7963 -0.4212 0.7220 11.00000 0.05 0.76 Q6 1 0.5043 -0.1986 0.5065 11.00000 0.05 0.63 Q7 1 0.7556 -0.3568 0.5221 11.00000 0.05 0.53 Q8 1 0.4934 -0.1337 0.7650 11.00000 0.05 0.48 Q9 1 0.9645 -0.3957 0.7534 11.00000 0.05 0.42 Q10 1 0.9297 -0.2539 0.6984 11.00000 0.05 0.40 ; _shelx_res_checksum 46055 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C6A C 0.9120(18) -0.3305(12) 0.6537(12) 0.027(4) Uiso 0.401(16) 1 d D . P A 1 C7A C 0.7091(16) -0.4241(16) 0.6077(15) 0.043(4) Uiso 0.401(16) 1 d D . P A 1 H7A1 H 0.6877 -0.4238 0.6827 0.065 Uiso 0.401(16) 1 calc R U P A 1 H7A2 H 0.6672 -0.5211 0.5568 0.065 Uiso 0.401(16) 1 calc R U P A 1 H7A3 H 0.6431 -0.3870 0.5542 0.065 Uiso 0.401(16) 1 calc R U P A 1 C8A C 0.941(2) -0.319(2) 0.5377(15) 0.056(5) Uiso 0.401(16) 1 d D . P A 1 H8A1 H 0.8675 -0.2842 0.4882 0.085 Uiso 0.401(16) 1 calc R U P A 1 H8A2 H 0.9052 -0.4126 0.4831 0.085 Uiso 0.401(16) 1 calc R U P A 1 H8A3 H 1.0685 -0.2532 0.5666 0.085 Uiso 0.401(16) 1 calc R U P A 1 C9A C 1.0068(16) -0.4016(15) 0.7236(13) 0.025(3) Uiso 0.401(16) 1 d D . P A 1 H9A1 H 1.1314 -0.3561 0.7378 0.037 Uiso 0.401(16) 1 calc R U P A 1 H9A2 H 0.9430 -0.5022 0.6709 0.037 Uiso 0.401(16) 1 calc R U P A 1 H9A3 H 1.0067 -0.3919 0.8070 0.037 Uiso 0.401(16) 1 calc R U P A 1 C6B C 0.8825(14) -0.3404(9) 0.6607(9) 0.029(3) Uiso 0.599(16) 1 d D . P A 2 C7B C 0.7252(14) -0.4319(12) 0.6793(11) 0.047(3) Uiso 0.599(16) 1 d D . P A 2 H7B1 H 0.7656 -0.4160 0.7714 0.071 Uiso 0.599(16) 1 calc R U P A 2 H7B2 H 0.6762 -0.5317 0.6317 0.071 Uiso 0.599(16) 1 calc R U P A 2 H7B3 H 0.6314 -0.4075 0.6471 0.071 Uiso 0.599(16) 1 calc R U P A 2 C8B C 0.8192(15) -0.3536(12) 0.5194(9) 0.044(3) Uiso 0.599(16) 1 d D . P A 2 H8B1 H 0.7191 -0.3354 0.4906 0.067 Uiso 0.599(16) 1 calc R U P A 2 H8B2 H 0.7787 -0.4493 0.4663 0.067 Uiso 0.599(16) 1 calc R U P A 2 H8B3 H 0.9191 -0.2844 0.5107 0.067 Uiso 0.599(16) 1 calc R U P A 2 C9B C 1.0230(17) -0.3869(17) 0.6959(14) 0.061(4) Uiso 0.599(16) 1 d D . P A 2 H9B1 H 1.1180 -0.3320 0.6754 0.092 Uiso 0.599(16) 1 calc R U P A 2 H9B2 H 0.9646 -0.4878 0.6465 0.092 Uiso 0.599(16) 1 calc R U P A 2 H9B3 H 1.0759 -0.3705 0.7884 0.092 Uiso 0.599(16) 1 calc R U P A 2 C1 C 0.8942(7) -0.1078(5) 0.7301(5) 0.0283(10) Uani 1 1 d . . . . . C4 C 1.1616(8) 0.0113(6) 0.9120(5) 0.0391(13) Uani 1 1 d . . . . . H4 H 1.2621 0.0843 0.9900 0.047 Uiso 1 1 calc R U . . . C3 C 1.1375(7) -0.1153(6) 0.8576(5) 0.0359(12) Uani 1 1 d . . . . . H3 H 1.2177 -0.1487 0.8896 0.043 Uiso 1 1 calc R U . . . C10 C 0.9825(8) 0.1328(6) 0.8639(6) 0.0362(12) Uani 1 1 d . . . . . H10A H 0.9813 0.1460 0.9478 0.043 Uiso 1 1 calc R U . . . H10B H 0.8620 0.1069 0.7973 0.043 Uiso 1 1 calc R U . . . C11 C 1.1209(7) 0.2711(5) 0.8709(5) 0.0281(10) Uani 1 1 d . . . . . C13 C 1.2621(7) 0.5126(6) 0.9612(5) 0.0287(11) Uani 1 1 d . . . . . C14 C 1.3531(7) 0.5316(6) 0.8885(5) 0.0303(11) Uani 1 1 d . . . . . H14 H 1.4332 0.6239 0.8962 0.036 Uiso 1 1 calc R U . . . C15 C 1.3240(7) 0.4124(6) 0.8042(5) 0.0313(11) Uani 1 1 d . . . . . H15 H 1.3844 0.4216 0.7533 0.038 Uiso 1 1 calc R U . . . C16 C 1.2058(7) 0.2798(6) 0.7953(5) 0.0302(11) Uani 1 1 d . . . . . H16 H 1.1836 0.1966 0.7383 0.036 Uiso 1 1 calc R U . . . C17 C 1.2892(8) 0.6352(6) 1.0578(6) 0.0343(12) Uani 1 1 d . . . . . H17A H 1.1708 0.6208 1.0461 0.041 Uiso 1 1 calc R U . . . H17B H 1.3580 0.6413 1.1464 0.041 Uiso 1 1 calc R U . . . C19 C 1.4440(8) 0.8835(6) 1.1441(6) 0.0424(14) Uani 1 1 d . . . . . H19A H 1.3398 0.8793 1.1515 0.064 Uiso 1 1 calc R U . . . H19B H 1.5058 0.9692 1.1278 0.064 Uiso 1 1 calc R U . . . H19C H 1.5273 0.8855 1.2246 0.064 Uiso 1 1 calc R U . . . C20 C 0.7584(8) -0.0644(7) 0.4958(6) 0.0379(13) Uani 1 1 d . . . . . C22 C 0.4193(8) -0.1847(6) 0.4701(6) 0.0393(13) Uani 1 1 d . . . . . N5 N 1.0134(6) 0.0157(5) 0.8336(4) 0.0313(10) Uani 1 1 d D . . . . N2 N 0.9726(6) -0.1884(5) 0.7452(4) 0.0297(9) Uani 1 1 d . . . . . N12 N 1.1476(6) 0.3852(5) 0.9535(4) 0.0272(9) Uani 1 1 d . . . . . O18 O 1.3851(6) 0.7629(4) 1.0408(4) 0.0427(10) Uani 1 1 d . . . . . O21 O 0.8206(6) -0.0143(5) 0.4424(4) 0.0458(10) Uani 1 1 d . . . . . O23 O 0.2813(6) -0.2126(5) 0.3963(5) 0.0562(13) Uani 1 1 d . . . . . Br Br 0.51080(9) -0.23075(7) 0.72700(6) 0.04674(16) Uani 1 1 d . . . . . Ir Ir 0.64928(3) -0.14476(2) 0.59172(2) 0.02895(8) 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 C1 0.031(3) 0.023(2) 0.025(2) 0.007(2) 0.014(2) 0.010(2) C4 0.032(3) 0.034(3) 0.026(3) 0.008(2) 0.006(2) 0.003(2) C3 0.025(3) 0.036(3) 0.029(3) 0.013(2) 0.004(2) 0.008(2) C10 0.033(3) 0.028(3) 0.036(3) 0.002(2) 0.020(2) 0.007(2) C11 0.025(2) 0.028(3) 0.026(2) 0.007(2) 0.010(2) 0.011(2) C13 0.025(2) 0.033(3) 0.027(2) 0.011(2) 0.007(2) 0.017(2) C14 0.030(3) 0.032(3) 0.032(3) 0.020(2) 0.014(2) 0.017(2) C15 0.033(3) 0.043(3) 0.030(3) 0.021(2) 0.018(2) 0.025(2) C16 0.032(3) 0.034(3) 0.023(2) 0.008(2) 0.013(2) 0.017(2) C17 0.035(3) 0.030(3) 0.038(3) 0.011(2) 0.016(2) 0.018(2) C19 0.033(3) 0.031(3) 0.048(3) 0.002(3) 0.013(3) 0.015(3) C20 0.032(3) 0.042(3) 0.030(3) 0.004(3) 0.000(2) 0.025(3) C22 0.037(3) 0.024(3) 0.050(3) 0.012(2) 0.015(3) 0.015(2) N5 0.032(2) 0.023(2) 0.030(2) 0.0057(18) 0.0162(19) 0.0065(18) N2 0.028(2) 0.026(2) 0.025(2) 0.0068(17) 0.0085(18) 0.0087(18) N12 0.024(2) 0.029(2) 0.025(2) 0.0057(17) 0.0103(17) 0.0128(18) O18 0.052(3) 0.025(2) 0.046(2) 0.0108(18) 0.022(2) 0.0174(19) O21 0.041(2) 0.061(3) 0.042(2) 0.024(2) 0.020(2) 0.029(2) O23 0.033(2) 0.040(2) 0.074(3) 0.019(2) 0.006(2) 0.018(2) Br 0.0450(3) 0.0362(3) 0.0476(3) 0.0119(3) 0.0247(3) 0.0099(3) Ir 0.02744(12) 0.02133(11) 0.03095(12) 0.00564(8) 0.01044(9) 0.01066(8) 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' 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 C8A C6A N2 112.1(11) . . ? C8A C6A C9A 110.5(10) . . ? N2 C6A C9A 110.8(9) . . ? C8A C6A C7A 108.9(10) . . ? N2 C6A C7A 106.8(10) . . ? C9A C6A C7A 107.6(9) . . ? C6A C7A H7A1 109.5 . . ? C6A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C6A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C6A C8A H8A1 109.5 . . ? C6A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C6A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C6A C9A H9A1 109.5 . . ? C6A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C6A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? N2 C6B C7B 110.2(8) . . ? N2 C6B C8B 109.8(7) . . ? C7B C6B C8B 110.3(8) . . ? N2 C6B C9B 108.3(9) . . ? C7B C6B C9B 111.0(8) . . ? C8B C6B C9B 107.2(8) . . ? C6B C7B H7B1 109.5 . . ? C6B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C6B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? C6B C8B H8B1 109.5 . . ? C6B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C6B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? C6B C9B H9B1 109.5 . . ? C6B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C6B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N2 C1 N5 104.7(4) . . ? N2 C1 Ir 132.8(4) . . ? N5 C1 Ir 122.5(4) . . ? C3 C4 N5 107.2(5) . . ? C3 C4 H4 126.4 . . ? N5 C4 H4 126.4 . . ? C4 C3 N2 107.1(5) . . ? C4 C3 H3 126.5 . . ? N2 C3 H3 126.5 . . ? N5 C10 C11 114.2(4) . . ? N5 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? N5 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? N12 C11 C16 123.3(5) . . ? N12 C11 C10 113.5(4) . . ? C16 C11 C10 123.1(5) . . ? N12 C13 C14 123.2(5) . . ? N12 C13 C17 114.7(5) . . ? C14 C13 C17 122.1(5) . . ? C15 C14 C13 118.2(5) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C16 C15 C14 119.2(5) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C11 C16 C15 118.6(5) . . ? C11 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? O18 C17 C13 109.7(5) . . ? O18 C17 H17A 109.7 . . ? C13 C17 H17A 109.7 . . ? O18 C17 H17B 109.7 . . ? C13 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? O18 C19 H19A 109.5 . . ? O18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O21 C20 Ir 177.5(6) . . ? O23 C22 Ir 177.9(5) . . ? C1 N5 C4 110.8(5) . . ? C1 N5 C10 124.9(5) . . ? C4 N5 C10 124.1(5) . . ? C1 N2 C3 110.2(5) . . ? C1 N2 C6B 124.2(5) . . ? C3 N2 C6B 125.2(5) . . ? C1 N2 C6A 128.8(6) . . ? C3 N2 C6A 120.7(6) . . ? C13 N12 C11 117.5(4) . . ? C19 O18 C17 111.7(5) . . ? C20 Ir C22 92.2(2) . . ? C20 Ir C1 91.0(2) . . ? C22 Ir C1 176.8(2) . . ? C20 Ir Br 175.22(18) . . ? C22 Ir Br 87.6(2) . . ? C1 Ir Br 89.21(14) . . ? 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 C6A C8A 1.510(13) . ? C6A N2 1.510(12) . ? C6A C9A 1.529(12) . ? C6A C7A 1.538(13) . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C7A H7A3 0.9800 . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C6B N2 1.503(9) . ? C6B C7B 1.508(11) . ? C6B C8B 1.529(11) . ? C6B C9B 1.535(11) . ? C7B H7B1 0.9800 . ? C7B H7B2 0.9800 . ? C7B H7B3 0.9800 . ? C8B H8B1 0.9800 . ? C8B H8B2 0.9800 . ? C8B H8B3 0.9800 . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C1 N2 1.362(7) . ? C1 N5 1.363(6) . ? C1 Ir 2.084(5) . ? C4 C3 1.341(9) . ? C4 N5 1.379(8) . ? C4 H4 0.9500 . ? C3 N2 1.393(7) . ? C3 H3 0.9500 . ? C10 N5 1.461(7) . ? C10 C11 1.505(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N12 1.345(7) . ? C11 C16 1.377(7) . ? C13 N12 1.336(7) . ? C13 C14 1.389(8) . ? C13 C17 1.502(7) . ? C14 C15 1.387(8) . ? C14 H14 0.9500 . ? C15 C16 1.384(8) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O18 1.423(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C19 O18 1.413(7) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O21 1.073(8) . ? C20 Ir 1.875(7) . ? C22 O23 1.130(7) . ? C22 Ir 1.901(6) . ? Br Ir 2.4670(7) . ?