# Electronic Supplementary Material (ESI) for Chemical Communications # 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_1 _database_code_depnum_ccdc_archive 'CCDC 883047' #TrackingRef 'MIA159ac_sanz.cif' _audit_creation_date 2012-02-28T21:02:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H20 I2 Ir N4 O2, B F4, C3 H6 O' _chemical_formula_sum 'C16 H26 B F4 I2 Ir N4 O3' _chemical_formula_weight 855.22 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 19.5550(14) _cell_length_b 10.6594(8) _cell_length_c 11.3757(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2371.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6159 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 29.57 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 2.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 8.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_absorpt_correction_T_min 0.6177 _exptl_absorpt_correction_T_max 0.7454 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_unetI/netI 0.034 _diffrn_reflns_number 24968 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 29.57 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 0.96 _reflns_number_total 6159 _reflns_number_gt 5962 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0457P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6159 _refine_ls_number_parmeters 284 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0252 _refine_ls_wR_factor_ref 0.065 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 2815 Friedel Pairs' _refine_ls_abs_structure_Flack 0.008(5) _refine_diff_density_max 1.517 _refine_diff_density_min -1.284 _refine_diff_density_rms 0.151 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.717726(7) 0.754472(13) 0.52438(3) 0.01260(5) Uani 1 1 d . . . I1 I 0.761181(14) 0.52072(2) 0.56609(3) 0.02096(7) Uani 1 1 d . . . I2 I 0.674382(14) 0.98646(2) 0.48048(2) 0.01827(6) Uani 1 1 d . . . N11 N 0.84148(18) 0.8615(3) 0.6393(3) 0.0189(7) Uani 1 1 d . . . C12 C 0.7787(2) 0.8091(4) 0.6507(4) 0.0156(8) Uani 1 1 d . . . N13 N 0.7707(2) 0.7913(4) 0.7678(4) 0.0202(8) Uani 1 1 d . . . C14 C 0.8288(2) 0.8298(4) 0.8272(4) 0.0238(10) Uani 1 1 d . . . H14 H 0.8358 0.8261 0.9097 0.029 Uiso 1 1 calc R . . C15 C 0.8731(2) 0.8731(4) 0.7479(4) 0.0241(9) Uani 1 1 d . . . H15 H 0.9176 0.9054 0.7629 0.029 Uiso 1 1 calc R . . N21 N 0.85204(17) 0.8383(4) 0.4302(3) 0.0186(7) Uani 1 1 d . . . C22 C 0.7927(2) 0.7756(4) 0.4136(4) 0.0166(8) Uani 1 1 d . . . N23 N 0.7984(2) 0.7238(4) 0.3050(4) 0.0192(7) Uani 1 1 d . . . C24 C 0.8597(3) 0.7578(4) 0.2536(5) 0.0229(10) Uani 1 1 d . . . H24 H 0.875 0.7352 0.1772 0.027 Uiso 1 1 calc R . . C25 C 0.8937(2) 0.8290(5) 0.3320(4) 0.0224(9) Uani 1 1 d . . . H25 H 0.9376 0.8656 0.322 0.027 Uiso 1 1 calc R . . C31 C 0.8669(2) 0.9164(4) 0.5321(4) 0.0214(8) Uani 1 1 d . . . H311 H 0.917 0.9282 0.5386 0.026 Uiso 1 1 calc R . . H312 H 0.8458 1 0.521 0.026 Uiso 1 1 calc R . . C41 C 0.7092(3) 0.7404(4) 0.8215(5) 0.0244(11) Uani 1 1 d . . . H411 H 0.7084 0.7631 0.9059 0.029 Uiso 1 1 calc R . . H412 H 0.7101 0.6478 0.8158 0.029 Uiso 1 1 calc R . . C42 C 0.6446(2) 0.7900(5) 0.7623(4) 0.0215(9) Uani 1 1 d . . . H421 H 0.6048 0.7742 0.8139 0.026 Uiso 1 1 calc R . . H422 H 0.6487 0.8818 0.7511 0.026 Uiso 1 1 calc R . . O43 O 0.63326(17) 0.7311(3) 0.6502(3) 0.0172(6) Uani 1 1 d . . . C44 C 0.5978(2) 0.6126(4) 0.6633(5) 0.0256(10) Uani 1 1 d . . . H441 H 0.6244 0.5571 0.7145 0.038 Uiso 1 1 calc R . . H442 H 0.5923 0.5732 0.586 0.038 Uiso 1 1 calc R . . H443 H 0.5527 0.6272 0.6981 0.038 Uiso 1 1 calc R . . C51 C 0.7457(2) 0.6460(5) 0.2522(4) 0.0238(9) Uani 1 1 d . . . H511 H 0.7456 0.563 0.2912 0.029 Uiso 1 1 calc R . . H512 H 0.7567 0.6328 0.1682 0.029 Uiso 1 1 calc R . . C52 C 0.6752(2) 0.7031(5) 0.2618(4) 0.0212(9) Uani 1 1 d . . . H521 H 0.6771 0.7931 0.2405 0.025 Uiso 1 1 calc R . . H522 H 0.6436 0.6604 0.2069 0.025 Uiso 1 1 calc R . . O53 O 0.65076(15) 0.6895(3) 0.3810(3) 0.0178(6) Uani 1 1 d . . . C54 C 0.5782(2) 0.7207(5) 0.3826(5) 0.0222(9) Uani 1 1 d . . . H541 H 0.5706 0.798 0.3379 0.033 Uiso 1 1 calc R . . H542 H 0.5632 0.7328 0.464 0.033 Uiso 1 1 calc R . . H543 H 0.552 0.6521 0.3469 0.033 Uiso 1 1 calc R . . B1 B 0.4899(2) 0.3469(4) 0.5266(5) 0.0217(9) Uani 1 1 d . . . F11 F 0.54027(17) 0.2572(3) 0.5228(8) 0.0389(8) Uani 1 1 d . . . F12 F 0.48945(15) 0.4089(3) 0.6335(2) 0.0296(6) Uani 1 1 d . . . F13 F 0.42545(15) 0.2921(3) 0.5105(3) 0.0352(7) Uani 1 1 d . . . F14 F 0.50064(18) 0.4339(3) 0.4365(3) 0.0398(7) Uani 1 1 d . . . O61 O 0.46743(17) 0.7851(4) 0.5812(4) 0.0345(9) Uani 1 1 d . . . C62 C 0.4635(2) 0.8991(5) 0.5853(5) 0.0267(10) Uani 1 1 d . . . C63 C 0.4644(4) 0.9671(9) 0.6984(7) 0.062(2) Uani 1 1 d . . . H631 H 0.4193 1.004 0.713 0.093 Uiso 1 1 calc R . . H632 H 0.4988 1.0338 0.6954 0.093 Uiso 1 1 calc R . . H633 H 0.4757 0.9087 0.762 0.093 Uiso 1 1 calc R . . C64 C 0.4569(3) 0.9761(5) 0.4762(7) 0.0348(11) Uani 1 1 d . . . H641 H 0.5021 1.007 0.4527 0.052 Uiso 1 1 calc R . . H642 H 0.4266 1.0474 0.4912 0.052 Uiso 1 1 calc R . . H643 H 0.4378 0.9244 0.413 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01311(7) 0.01225(7) 0.01243(7) -0.00049(5) 0.00044(6) -0.00153(4) I1 0.02474(13) 0.01428(13) 0.02387(13) -0.00041(12) -0.00259(12) 0.00242(9) I2 0.02228(12) 0.01330(12) 0.01925(12) 0.00037(12) -0.00329(11) -0.00016(9) N11 0.0190(16) 0.0174(17) 0.0201(18) -0.0044(15) -0.0039(15) -0.0006(13) C12 0.0157(18) 0.0151(19) 0.0160(19) -0.0026(16) 0.0004(16) 0.0040(14) N13 0.0227(18) 0.021(2) 0.0171(19) -0.0022(16) -0.0014(15) 0.0036(16) C14 0.028(2) 0.024(2) 0.019(2) -0.0082(18) -0.0097(19) 0.0066(17) C15 0.025(2) 0.023(2) 0.025(2) -0.0083(18) -0.0087(19) 0.0028(18) N21 0.0167(16) 0.0188(17) 0.0202(18) 0.0034(14) 0.0009(14) -0.0017(13) C22 0.020(2) 0.0159(18) 0.014(2) 0.0003(17) 0.0020(16) -0.0004(16) N23 0.0205(17) 0.0225(18) 0.0146(19) -0.0011(16) 0.0037(16) 0.0018(16) C24 0.022(2) 0.026(2) 0.020(2) 0.0052(17) 0.008(2) 0.0050(16) C25 0.0163(18) 0.025(2) 0.025(2) 0.0074(19) 0.0036(18) 0.0033(16) C31 0.0193(17) 0.0195(18) 0.025(2) -0.0016(19) -0.0043(18) -0.0061(15) C41 0.029(3) 0.029(3) 0.014(2) 0.0013(17) 0.000(2) 0.0024(17) C42 0.025(2) 0.023(2) 0.017(2) -0.0015(18) 0.0034(18) 0.0014(18) O43 0.0185(15) 0.0179(14) 0.0152(15) 0.0002(12) 0.0027(13) -0.0038(11) C44 0.025(2) 0.019(2) 0.032(2) 0.0047(19) 0.009(2) -0.0073(17) C51 0.025(2) 0.026(2) 0.021(2) -0.0064(19) 0.0010(18) 0.0000(18) C52 0.025(2) 0.022(2) 0.016(2) -0.0013(17) -0.0005(17) 0.0004(18) O53 0.0167(13) 0.0185(15) 0.0181(14) -0.0013(12) -0.0009(12) -0.0025(12) C54 0.0151(19) 0.024(2) 0.027(2) -0.001(2) -0.0024(18) -0.0003(17) B1 0.026(2) 0.020(2) 0.0190(19) 0.000(2) -0.007(2) 0.0016(17) F11 0.0358(16) 0.0312(16) 0.050(2) -0.0033(15) -0.001(2) 0.0132(12) F12 0.0357(15) 0.0305(15) 0.0225(14) -0.0053(12) -0.0009(13) -0.0052(13) F13 0.0287(13) 0.0376(16) 0.0393(19) -0.0108(15) -0.0075(14) -0.0032(12) F14 0.0499(19) 0.0375(17) 0.0320(16) 0.0111(14) 0.0163(15) 0.0088(15) O61 0.031(2) 0.0287(19) 0.044(2) 0.003(2) 0.0092(18) -0.0037(14) C62 0.0161(19) 0.034(3) 0.030(3) -0.008(2) 0.0052(19) -0.0029(16) C63 0.068(5) 0.076(6) 0.042(4) -0.031(4) -0.002(4) -0.001(4) C64 0.033(2) 0.029(3) 0.042(3) 0.003(3) 0.005(3) -0.005(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C22 1.946(5) . ? Ir1 C12 1.955(4) . ? Ir1 O43 2.200(3) . ? Ir1 O53 2.204(3) . ? Ir1 I2 2.6614(3) . ? Ir1 I1 2.6750(3) . ? N11 C12 1.356(5) . ? N11 C15 1.388(6) . ? N11 C31 1.441(6) . ? C12 N13 1.355(6) . ? N13 C14 1.383(6) . ? N13 C41 1.454(7) . ? C14 C15 1.333(7) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? N21 C22 1.353(6) . ? N21 C25 1.387(6) . ? N21 C31 1.456(6) . ? C22 N23 1.357(6) . ? N23 C24 1.382(7) . ? N23 C51 1.453(6) . ? C24 C25 1.347(7) . ? C24 H24 0.95 . ? C25 H25 0.95 . ? C31 H311 0.99 . ? C31 H312 0.99 . ? C41 C42 1.526(7) . ? C41 H411 0.99 . ? C41 H412 0.99 . ? C42 O43 1.438(6) . ? C42 H421 0.99 . ? C42 H422 0.99 . ? O43 C44 1.449(5) . ? C44 H441 0.98 . ? C44 H442 0.98 . ? C44 H443 0.98 . ? C51 C52 1.510(6) . ? C51 H511 0.99 . ? C51 H512 0.99 . ? C52 O53 1.445(5) . ? C52 H521 0.99 . ? C52 H522 0.99 . ? O53 C54 1.457(5) . ? C54 H541 0.98 . ? C54 H542 0.98 . ? C54 H543 0.98 . ? B1 F11 1.374(5) . ? B1 F12 1.384(6) . ? B1 F14 1.398(6) . ? B1 F13 1.400(5) . ? O61 C62 1.218(7) . ? C62 C63 1.478(8) . ? C62 C64 1.493(9) . ? C63 H631 0.98 . ? C63 H632 0.98 . ? C63 H633 0.98 . ? C64 H641 0.98 . ? C64 H642 0.98 . ? C64 H643 0.98 . ? 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 C22 Ir1 C12 88.99(19) . . ? C22 Ir1 O43 179.75(19) . . ? C12 Ir1 O43 90.76(16) . . ? C22 Ir1 O53 90.25(17) . . ? C12 Ir1 O53 178.68(15) . . ? O43 Ir1 O53 89.99(12) . . ? C22 Ir1 I2 90.63(14) . . ? C12 Ir1 I2 93.16(12) . . ? O43 Ir1 I2 89.33(8) . . ? O53 Ir1 I2 87.93(8) . . ? C22 Ir1 I1 89.04(14) . . ? C12 Ir1 I1 87.34(12) . . ? O43 Ir1 I1 91.01(8) . . ? O53 Ir1 I1 91.57(8) . . ? I2 Ir1 I1 179.396(18) . . ? C12 N11 C15 110.9(4) . . ? C12 N11 C31 124.1(4) . . ? C15 N11 C31 124.3(4) . . ? N13 C12 N11 104.8(4) . . ? N13 C12 Ir1 127.7(3) . . ? N11 C12 Ir1 127.2(3) . . ? C12 N13 C14 110.1(4) . . ? C12 N13 C41 124.1(4) . . ? C14 N13 C41 125.8(4) . . ? C15 C14 N13 107.9(4) . . ? C15 C14 H14 126.1 . . ? N13 C14 H14 126.1 . . ? C14 C15 N11 106.3(4) . . ? C14 C15 H15 126.8 . . ? N11 C15 H15 126.8 . . ? C22 N21 C25 110.9(4) . . ? C22 N21 C31 124.4(4) . . ? C25 N21 C31 124.4(4) . . ? N21 C22 N23 104.9(4) . . ? N21 C22 Ir1 127.8(4) . . ? N23 C22 Ir1 127.2(4) . . ? C22 N23 C24 110.5(4) . . ? C22 N23 C51 123.3(4) . . ? C24 N23 C51 126.1(4) . . ? C25 C24 N23 107.2(4) . . ? C25 C24 H24 126.4 . . ? N23 C24 H24 126.4 . . ? C24 C25 N21 106.5(4) . . ? C24 C25 H25 126.8 . . ? N21 C25 H25 126.8 . . ? N11 C31 N21 111.9(3) . . ? N11 C31 H311 109.2 . . ? N21 C31 H311 109.2 . . ? N11 C31 H312 109.2 . . ? N21 C31 H312 109.2 . . ? H311 C31 H312 107.9 . . ? N13 C41 C42 111.7(4) . . ? N13 C41 H411 109.3 . . ? C42 C41 H411 109.3 . . ? N13 C41 H412 109.3 . . ? C42 C41 H412 109.3 . . ? H411 C41 H412 107.9 . . ? O43 C42 C41 111.6(4) . . ? O43 C42 H421 109.3 . . ? C41 C42 H421 109.3 . . ? O43 C42 H422 109.3 . . ? C41 C42 H422 109.3 . . ? H421 C42 H422 108 . . ? C42 O43 C44 111.3(4) . . ? C42 O43 Ir1 114.3(3) . . ? C44 O43 Ir1 121.7(3) . . ? O43 C44 H441 109.5 . . ? O43 C44 H442 109.5 . . ? H441 C44 H442 109.5 . . ? O43 C44 H443 109.5 . . ? H441 C44 H443 109.5 . . ? H442 C44 H443 109.5 . . ? N23 C51 C52 112.8(4) . . ? N23 C51 H511 109 . . ? C52 C51 H511 109 . . ? N23 C51 H512 109 . . ? C52 C51 H512 109 . . ? H511 C51 H512 107.8 . . ? O53 C52 C51 109.3(4) . . ? O53 C52 H521 109.8 . . ? C51 C52 H521 109.8 . . ? O53 C52 H522 109.8 . . ? C51 C52 H522 109.8 . . ? H521 C52 H522 108.3 . . ? C52 O53 C54 108.2(3) . . ? C52 O53 Ir1 117.8(3) . . ? C54 O53 Ir1 119.8(3) . . ? O53 C54 H541 109.5 . . ? O53 C54 H542 109.5 . . ? H541 C54 H542 109.5 . . ? O53 C54 H543 109.5 . . ? H541 C54 H543 109.5 . . ? H542 C54 H543 109.5 . . ? F11 B1 F12 111.4(5) . . ? F11 B1 F14 109.3(5) . . ? F12 B1 F14 109.2(4) . . ? F11 B1 F13 110.5(4) . . ? F12 B1 F13 108.0(4) . . ? F14 B1 F13 108.4(4) . . ? O61 C62 C63 121.4(6) . . ? O61 C62 C64 121.5(5) . . ? C63 C62 C64 117.1(6) . . ? C62 C63 H631 109.5 . . ? C62 C63 H632 109.5 . . ? H631 C63 H632 109.5 . . ? C62 C63 H633 109.5 . . ? H631 C63 H633 109.5 . . ? H632 C63 H633 109.5 . . ? C62 C64 H641 109.5 . . ? C62 C64 H642 109.5 . . ? H641 C64 H642 109.5 . . ? C62 C64 H643 109.5 . . ? H641 C64 H643 109.5 . . ? H642 C64 H643 109.5 . . ? 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 C15 N11 C12 N13 1.6(5) . . . . ? C31 N11 C12 N13 -168.9(4) . . . . ? C15 N11 C12 Ir1 -172.3(3) . . . . ? C31 N11 C12 Ir1 17.3(6) . . . . ? C22 Ir1 C12 N13 -161.4(4) . . . . ? O43 Ir1 C12 N13 18.7(4) . . . . ? I2 Ir1 C12 N13 108.0(4) . . . . ? I1 Ir1 C12 N13 -72.3(4) . . . . ? C22 Ir1 C12 N11 11.1(4) . . . . ? O43 Ir1 C12 N11 -168.8(4) . . . . ? I2 Ir1 C12 N11 -79.5(4) . . . . ? I1 Ir1 C12 N11 100.2(4) . . . . ? N11 C12 N13 C14 -1.3(5) . . . . ? Ir1 C12 N13 C14 172.5(3) . . . . ? N11 C12 N13 C41 177.9(4) . . . . ? Ir1 C12 N13 C41 -8.3(7) . . . . ? C12 N13 C14 C15 0.6(5) . . . . ? C41 N13 C14 C15 -178.6(4) . . . . ? N13 C14 C15 N11 0.4(5) . . . . ? C12 N11 C15 C14 -1.3(5) . . . . ? C31 N11 C15 C14 169.2(4) . . . . ? C25 N21 C22 N23 1.7(5) . . . . ? C31 N21 C22 N23 175.4(4) . . . . ? C25 N21 C22 Ir1 178.1(3) . . . . ? C31 N21 C22 Ir1 -8.2(6) . . . . ? C12 Ir1 C22 N21 -15.3(4) . . . . ? O53 Ir1 C22 N21 165.8(4) . . . . ? I2 Ir1 C22 N21 77.8(4) . . . . ? I1 Ir1 C22 N21 -102.7(4) . . . . ? C12 Ir1 C22 N23 160.3(4) . . . . ? O53 Ir1 C22 N23 -18.6(4) . . . . ? I2 Ir1 C22 N23 -106.6(4) . . . . ? I1 Ir1 C22 N23 72.9(4) . . . . ? N21 C22 N23 C24 -2.0(5) . . . . ? Ir1 C22 N23 C24 -178.5(3) . . . . ? N21 C22 N23 C51 179.2(4) . . . . ? Ir1 C22 N23 C51 2.8(7) . . . . ? C22 N23 C24 C25 1.7(5) . . . . ? C51 N23 C24 C25 -179.6(4) . . . . ? N23 C24 C25 N21 -0.6(5) . . . . ? C22 N21 C25 C24 -0.7(5) . . . . ? C31 N21 C25 C24 -174.4(4) . . . . ? C12 N11 C31 N21 -44.4(5) . . . . ? C15 N11 C31 N21 146.4(4) . . . . ? C22 N21 C31 N11 39.7(6) . . . . ? C25 N21 C31 N11 -147.4(4) . . . . ? C12 N13 C41 C42 -39.2(6) . . . . ? C14 N13 C41 C42 139.8(5) . . . . ? N13 C41 C42 O43 75.3(5) . . . . ? C41 C42 O43 C44 84.4(5) . . . . ? C41 C42 O43 Ir1 -58.2(4) . . . . ? C12 Ir1 O43 C42 14.9(3) . . . . ? O53 Ir1 O43 C42 -166.2(3) . . . . ? I2 Ir1 O43 C42 -78.3(3) . . . . ? I1 Ir1 O43 C42 102.2(3) . . . . ? C12 Ir1 O43 C44 -123.4(3) . . . . ? O53 Ir1 O43 C44 55.5(3) . . . . ? I2 Ir1 O43 C44 143.4(3) . . . . ? I1 Ir1 O43 C44 -36.1(3) . . . . ? C22 N23 C51 C52 47.7(6) . . . . ? C24 N23 C51 C52 -130.9(5) . . . . ? N23 C51 C52 O53 -75.1(5) . . . . ? C51 C52 O53 C54 -168.3(4) . . . . ? C51 C52 O53 Ir1 51.9(4) . . . . ? C22 Ir1 O53 C52 -10.2(3) . . . . ? O43 Ir1 O53 C52 169.8(3) . . . . ? I2 Ir1 O53 C52 80.4(3) . . . . ? I1 Ir1 O53 C52 -99.2(3) . . . . ? C22 Ir1 O53 C54 -145.3(3) . . . . ? O43 Ir1 O53 C54 34.7(3) . . . . ? I2 Ir1 O53 C54 -54.6(3) . . . . ? I1 Ir1 O53 C54 125.7(3) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF