# Electronic Supplementary Material (ESI) for Chemical Communications # 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_09078 #TrackingRef 'Shalini 4 SI.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H30 Ir N3 O2, C H Cl3' _chemical_formula_sum 'C35 H31 Cl3 Ir N3 O2' _chemical_formula_weight 824.18 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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.355(5) _cell_length_b 14.083(8) _cell_length_c 24.255(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3196(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 942 _cell_measurement_theta_min 2.217 _cell_measurement_theta_max 26.766 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 4.466 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.441 _exptl_absorpt_correction_T_max 0.802 _exptl_absorpt_process_details ; absorption correction based on 17160 reflections(SADABS);Rint 0.1541 before correction and 0.0599 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex 2000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26714 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.99 _reflns_number_total 6950 _reflns_number_gt 6466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0278P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(7) _chemical_absolute_configuration ,rm _refine_ls_number_reflns 6950 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.02656(2) -0.024317(14) 0.861581(8) 0.02073(6) Uani 1 1 d . . . O1 O 0.1364(5) -0.1241(3) 0.81151(18) 0.0322(10) Uani 1 1 d . . . O2 O 0.1794(4) 0.1410(4) 0.72520(17) 0.0398(11) Uani 1 1 d . . . N1 N 0.1971(5) -0.0024(3) 0.91194(18) 0.0228(11) Uani 1 1 d . . . N2 N -0.1595(5) -0.0484(3) 0.81978(19) 0.0254(11) Uani 1 1 d . . . N3 N 0.0999(5) 0.0806(3) 0.80425(19) 0.0259(11) Uani 1 1 d . . . C1 C 0.3274(6) -0.0394(4) 0.9034(2) 0.0293(14) Uani 1 1 d . . . H1 H 0.3429 -0.0772 0.8715 0.035 Uiso 1 1 calc R . . C2 C 0.4401(5) -0.0243(5) 0.9394(2) 0.0320(13) Uani 1 1 d . . . H2 H 0.5321 -0.0501 0.9322 0.038 Uiso 1 1 calc R . . C3 C 0.4141(7) 0.0302(5) 0.9866(2) 0.0395(15) Uani 1 1 d . . . H3 H 0.4889 0.0416 1.0122 0.047 Uiso 1 1 calc R . . C4 C 0.2809(7) 0.0670(5) 0.9959(2) 0.0338(15) Uani 1 1 d . . . H4 H 0.2631 0.1036 1.0280 0.041 Uiso 1 1 calc R . . C5 C 0.1708(6) 0.0507(3) 0.9579(2) 0.0227(13) Uani 1 1 d . . . C6 C 0.0254(7) 0.0880(3) 0.96051(19) 0.0226(11) Uani 1 1 d . . . C7 C -0.0234(8) 0.1481(4) 1.0031(2) 0.0319(13) Uani 1 1 d . . . H7 H 0.0382 0.1642 1.0328 0.038 Uiso 1 1 calc R . . C8 C -0.1589(7) 0.1828(4) 1.0014(2) 0.0356(16) Uani 1 1 d . . . H8 H -0.1920 0.2233 1.0300 0.043 Uiso 1 1 calc R . . C9 C -0.2496(7) 0.1592(4) 0.9580(3) 0.0347(16) Uani 1 1 d . . . H9 H -0.3440 0.1839 0.9568 0.042 Uiso 1 1 calc R . . C10 C -0.2022(6) 0.1001(4) 0.9168(3) 0.0302(14) Uani 1 1 d . . . H10 H -0.2658 0.0836 0.8878 0.036 Uiso 1 1 calc R . . C11 C -0.0623(6) 0.0634(4) 0.9163(2) 0.0228(12) Uani 1 1 d . . . C12 C -0.2069(6) 0.0044(4) 0.7772(2) 0.0287(15) Uani 1 1 d . . . H12 H -0.1479 0.0540 0.7636 0.034 Uiso 1 1 calc R . . C13 C -0.3370(6) -0.0108(5) 0.7527(2) 0.0382(16) Uani 1 1 d . . . H13 H -0.3671 0.0270 0.7224 0.046 Uiso 1 1 calc R . . C14 C -0.4232(7) -0.0821(5) 0.7730(3) 0.0411(16) Uani 1 1 d . . . H14 H -0.5145 -0.0933 0.7572 0.049 Uiso 1 1 calc R . . C15 C -0.3764(6) -0.1366(5) 0.8161(3) 0.0391(16) Uani 1 1 d . . . H15 H -0.4346 -0.1866 0.8297 0.047 Uiso 1 1 calc R . . C16 C -0.2432(6) -0.1188(4) 0.8399(2) 0.0262(13) Uani 1 1 d . . . C17 C -0.1807(6) -0.1700(4) 0.8872(3) 0.0287(14) Uani 1 1 d . . . C18 C -0.2416(7) -0.2501(4) 0.9106(3) 0.0394(16) Uani 1 1 d . . . H18 H -0.3266 -0.2761 0.8954 0.047 Uiso 1 1 calc R . . C19 C -0.1790(8) -0.2921(5) 0.9558(3) 0.0453(19) Uani 1 1 d . . . H19 H -0.2222 -0.3458 0.9727 0.054 Uiso 1 1 calc R . . C20 C -0.0527(7) -0.2555(4) 0.9765(3) 0.0386(16) Uani 1 1 d . . . H20 H -0.0078 -0.2850 1.0072 0.046 Uiso 1 1 calc R . . C21 C 0.0080(7) -0.1765(4) 0.9526(2) 0.0330(14) Uani 1 1 d . . . H21 H 0.0930 -0.1511 0.9682 0.040 Uiso 1 1 calc R . . C22 C -0.0508(6) -0.1323(4) 0.9062(2) 0.0249(13) Uani 1 1 d . . . C23 C 0.1919(6) -0.1128(5) 0.7622(3) 0.0309(15) Uani 1 1 d . . . C24 C 0.2446(7) -0.1954(5) 0.7360(3) 0.0382(17) Uani 1 1 d . . . H24 H 0.2376 -0.2551 0.7540 0.046 Uiso 1 1 calc R . . C25 C 0.3066(7) -0.1898(6) 0.6840(3) 0.050(2) Uani 1 1 d . . . H25 H 0.3414 -0.2460 0.6670 0.061 Uiso 1 1 calc R . . C26 C 0.3183(8) -0.1060(7) 0.6571(3) 0.057(2) Uani 1 1 d . . . H26 H 0.3610 -0.1035 0.6216 0.068 Uiso 1 1 calc R . . C27 C 0.2683(7) -0.0251(7) 0.6814(2) 0.0513(18) Uani 1 1 d . . . H27 H 0.2767 0.0333 0.6620 0.062 Uiso 1 1 calc R . . C28 C 0.2051(6) -0.0249(6) 0.7338(2) 0.0365(15) Uani 1 1 d . . . C29 C 0.1595(6) 0.0636(5) 0.7572(2) 0.0308(15) Uani 1 1 d . . . C30 C 0.1068(7) 0.2196(5) 0.7510(2) 0.0368(16) Uani 1 1 d . . . H30A H 0.0166 0.2346 0.7314 0.044 Uiso 1 1 calc R . . H30B H 0.1681 0.2769 0.7514 0.044 Uiso 1 1 calc R . . C31 C 0.0768(6) 0.1843(4) 0.8098(2) 0.0265(13) Uani 1 1 d . . . H31 H -0.0257 0.1965 0.8192 0.032 Uiso 1 1 calc R . . C32 C 0.1713(6) 0.2299(4) 0.8533(3) 0.0317(14) Uani 1 1 d . . . H32 H 0.1512 0.1963 0.8888 0.038 Uiso 1 1 calc R . . C33 C 0.1290(8) 0.3334(4) 0.8616(3) 0.0460(16) Uani 1 1 d . . . H33A H 0.1875 0.3611 0.8910 0.069 Uiso 1 1 calc R . . H33B H 0.0278 0.3369 0.8719 0.069 Uiso 1 1 calc R . . H33C H 0.1445 0.3686 0.8273 0.069 Uiso 1 1 calc R . . C34 C 0.3289(7) 0.2183(5) 0.8420(3) 0.0425(17) Uani 1 1 d . . . H34A H 0.3501 0.1512 0.8351 0.064 Uiso 1 1 calc R . . H34B H 0.3836 0.2403 0.8740 0.064 Uiso 1 1 calc R . . H34C H 0.3552 0.2560 0.8096 0.064 Uiso 1 1 calc R . . C35 C 0.2263(8) 0.6383(5) 0.9045(3) 0.0501(19) Uani 1 1 d . . . H35 H 0.1940 0.6984 0.9225 0.060 Uiso 1 1 calc R . . Cl1 Cl 0.2646(3) 0.55539(19) 0.95562(12) 0.1044(11) Uani 1 1 d . . . Cl2 Cl 0.08898(18) 0.59640(13) 0.86273(9) 0.0532(4) Uani 1 1 d . . . Cl3 Cl 0.3805(3) 0.6615(2) 0.86751(11) 0.0953(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01988(9) 0.02187(9) 0.02045(9) -0.00419(9) 0.00249(9) -0.00150(9) O1 0.029(2) 0.035(2) 0.033(3) -0.012(2) 0.008(2) 0.000(2) O2 0.028(2) 0.067(3) 0.024(2) 0.007(2) 0.0048(19) 0.000(2) N1 0.025(2) 0.023(3) 0.021(2) 0.0038(18) -0.0014(19) -0.0061(17) N2 0.019(2) 0.032(3) 0.025(3) -0.008(2) 0.0034(19) 0.0003(19) N3 0.019(3) 0.036(3) 0.023(3) -0.001(2) -0.001(2) -0.002(2) C1 0.031(3) 0.032(4) 0.025(3) 0.003(3) 0.000(2) -0.003(3) C2 0.020(3) 0.036(3) 0.040(3) 0.004(3) -0.002(2) 0.004(3) C3 0.043(4) 0.040(4) 0.036(3) 0.011(3) -0.018(3) -0.012(3) C4 0.045(4) 0.033(3) 0.024(3) 0.003(3) -0.006(3) 0.000(3) C5 0.037(3) 0.015(3) 0.017(3) 0.004(2) 0.001(2) -0.006(2) C6 0.033(3) 0.018(2) 0.017(2) 0.0014(19) 0.004(3) -0.006(3) C7 0.056(4) 0.025(3) 0.014(3) -0.001(2) 0.002(3) -0.005(3) C8 0.053(4) 0.031(3) 0.023(3) -0.009(3) 0.016(3) 0.010(3) C9 0.040(4) 0.022(3) 0.042(4) 0.002(3) 0.018(3) 0.008(3) C10 0.030(3) 0.024(3) 0.036(4) 0.004(3) 0.005(3) -0.004(2) C11 0.026(3) 0.017(2) 0.025(3) 0.001(2) 0.008(2) -0.003(2) C12 0.023(3) 0.039(4) 0.024(3) -0.003(2) 0.002(2) -0.004(2) C13 0.028(3) 0.055(5) 0.031(3) 0.000(3) -0.006(3) 0.004(3) C14 0.024(3) 0.059(4) 0.041(4) -0.015(3) -0.005(3) 0.002(3) C15 0.020(3) 0.042(4) 0.055(4) -0.011(3) 0.006(3) -0.010(3) C16 0.020(3) 0.027(3) 0.032(3) -0.006(2) 0.013(2) -0.001(2) C17 0.025(3) 0.025(3) 0.036(3) -0.004(3) 0.011(3) -0.001(3) C18 0.031(4) 0.033(4) 0.054(4) 0.000(3) 0.011(3) -0.007(3) C19 0.047(5) 0.030(4) 0.059(5) 0.013(4) 0.021(4) -0.002(3) C20 0.048(5) 0.033(3) 0.036(4) 0.008(3) 0.011(3) 0.004(3) C21 0.030(4) 0.029(3) 0.040(3) -0.003(3) 0.005(3) 0.001(3) C22 0.026(4) 0.022(3) 0.026(3) -0.005(2) 0.009(2) 0.000(2) C23 0.015(3) 0.040(4) 0.038(4) -0.016(3) -0.005(3) -0.001(3) C24 0.025(3) 0.046(4) 0.044(4) -0.026(3) 0.006(3) -0.003(3) C25 0.030(4) 0.073(6) 0.048(5) -0.039(4) -0.002(3) 0.006(4) C26 0.037(4) 0.113(8) 0.021(4) -0.015(4) 0.001(3) 0.014(4) C27 0.038(4) 0.091(6) 0.025(3) -0.007(4) 0.007(3) 0.014(4) C28 0.020(3) 0.060(4) 0.029(3) -0.019(4) -0.005(2) 0.007(4) C29 0.023(3) 0.052(4) 0.018(3) 0.006(3) -0.007(2) -0.004(3) C30 0.032(4) 0.047(4) 0.032(4) 0.012(3) -0.004(3) -0.004(3) C31 0.023(3) 0.030(3) 0.027(3) 0.006(2) 0.000(2) -0.003(2) C32 0.032(3) 0.033(3) 0.030(4) 0.008(3) -0.003(3) -0.006(2) C33 0.065(5) 0.029(3) 0.044(4) 0.000(4) 0.003(4) -0.011(3) C34 0.036(4) 0.056(4) 0.036(4) 0.008(3) -0.008(3) -0.019(3) C35 0.055(5) 0.044(4) 0.051(5) -0.008(4) -0.004(4) -0.004(4) Cl1 0.116(2) 0.0895(19) 0.108(2) 0.0466(17) -0.0652(18) -0.0424(16) Cl2 0.0426(9) 0.0669(11) 0.0501(10) -0.0068(11) -0.0092(10) 0.0008(8) Cl3 0.0757(16) 0.137(2) 0.0734(17) -0.0222(17) 0.0179(14) -0.0596(16) _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 C11 1.994(5) . ? Ir1 C22 2.002(5) . ? Ir1 N1 2.033(4) . ? Ir1 N2 2.042(5) . ? Ir1 O1 2.123(4) . ? Ir1 N3 2.142(5) . ? O1 C23 1.313(8) . ? O2 C29 1.351(8) . ? O2 C30 1.441(8) . ? N1 C1 1.341(7) . ? N1 C5 1.364(7) . ? N2 C12 1.347(7) . ? N2 C16 1.355(7) . ? N3 C29 1.293(7) . ? N3 C31 1.483(7) . ? C1 C2 1.385(7) . ? C1 H1 0.9500 . ? C2 C3 1.401(8) . ? C2 H2 0.9500 . ? C3 C4 1.368(9) . ? C3 H3 0.9500 . ? C4 C5 1.401(8) . ? C4 H4 0.9500 . ? C5 C6 1.459(8) . ? C6 C11 1.395(7) . ? C6 C7 1.410(7) . ? C7 C8 1.360(9) . ? C7 H7 0.9500 . ? C8 C9 1.393(9) . ? C8 H8 0.9500 . ? C9 C10 1.373(8) . ? C9 H9 0.9500 . ? C10 C11 1.407(8) . ? C10 H10 0.9500 . ? C12 C13 1.371(8) . ? C12 H12 0.9500 . ? C13 C14 1.378(9) . ? C13 H13 0.9500 . ? C14 C15 1.368(9) . ? C14 H14 0.9500 . ? C15 C16 1.397(8) . ? C15 H15 0.9500 . ? C16 C17 1.476(8) . ? C17 C18 1.386(8) . ? C17 C22 1.404(8) . ? C18 C19 1.377(10) . ? C18 H18 0.9500 . ? C19 C20 1.383(10) . ? C19 H19 0.9500 . ? C20 C21 1.377(8) . ? C20 H20 0.9500 . ? C21 C22 1.400(8) . ? C21 H21 0.9500 . ? C23 C24 1.415(8) . ? C23 C28 1.422(10) . ? C24 C25 1.389(10) . ? C24 H24 0.9500 . ? C25 C26 1.353(11) . ? C25 H25 0.9500 . ? C26 C27 1.365(11) . ? C26 H26 0.9500 . ? C27 C28 1.401(8) . ? C27 H27 0.9500 . ? C28 C29 1.435(9) . ? C30 C31 1.538(8) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.517(8) . ? C31 H31 1.0000 . ? C32 C34 1.508(9) . ? C32 C33 1.524(8) . ? C32 H32 1.0000 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 Cl3 1.730(8) . ? C35 Cl2 1.739(7) . ? C35 Cl1 1.740(8) . ? C35 H35 1.0000 . ? 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 C11 Ir1 C22 87.7(2) . . ? C11 Ir1 N1 80.4(2) . . ? C22 Ir1 N1 94.2(2) . . ? C11 Ir1 N2 94.4(2) . . ? C22 Ir1 N2 80.5(2) . . ? N1 Ir1 N2 172.84(18) . . ? C11 Ir1 O1 173.0(2) . . ? C22 Ir1 O1 88.9(2) . . ? N1 Ir1 O1 93.68(18) . . ? N2 Ir1 O1 91.08(17) . . ? C11 Ir1 N3 97.9(2) . . ? C22 Ir1 N3 172.2(2) . . ? N1 Ir1 N3 91.94(17) . . ? N2 Ir1 N3 93.73(18) . . ? O1 Ir1 N3 85.98(17) . . ? C23 O1 Ir1 129.2(4) . . ? C29 O2 C30 107.8(5) . . ? C1 N1 C5 120.2(5) . . ? C1 N1 Ir1 124.2(4) . . ? C5 N1 Ir1 115.6(4) . . ? C12 N2 C16 119.3(5) . . ? C12 N2 Ir1 124.7(4) . . ? C16 N2 Ir1 115.8(4) . . ? C29 N3 C31 109.1(5) . . ? C29 N3 Ir1 125.7(4) . . ? C31 N3 Ir1 125.0(4) . . ? N1 C1 C2 122.4(5) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 117.8(5) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.0(6) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 119.6(5) . . ? N1 C5 C6 113.7(5) . . ? C4 C5 C6 126.7(5) . . ? C11 C6 C7 121.5(6) . . ? C11 C6 C5 115.1(5) . . ? C7 C6 C5 123.3(5) . . ? C8 C7 C6 119.7(6) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.3(5) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 119.9(6) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 122.0(6) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C6 C11 C10 116.6(5) . . ? C6 C11 Ir1 114.9(4) . . ? C10 C11 Ir1 128.4(4) . . ? N2 C12 C13 122.6(6) . . ? N2 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C14 118.6(6) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 119.6(6) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.1(6) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? N2 C16 C15 119.8(6) . . ? N2 C16 C17 114.1(5) . . ? C15 C16 C17 126.0(6) . . ? C18 C17 C22 122.0(6) . . ? C18 C17 C16 123.6(6) . . ? C22 C17 C16 114.4(5) . . ? C19 C18 C17 120.1(6) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 119.4(6) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C21 C20 C19 120.1(6) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 122.4(6) . . ? C20 C21 H21 118.8 . . ? C22 C21 H21 118.8 . . ? C21 C22 C17 115.8(5) . . ? C21 C22 Ir1 129.1(4) . . ? C17 C22 Ir1 115.0(4) . . ? O1 C23 C24 116.6(6) . . ? O1 C23 C28 125.6(6) . . ? C24 C23 C28 117.8(6) . . ? C25 C24 C23 120.5(7) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 121.4(7) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C25 C26 C27 119.5(7) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C26 C27 C28 122.5(9) . . ? C26 C27 H27 118.8 . . ? C28 C27 H27 118.8 . . ? C27 C28 C23 118.4(7) . . ? C27 C28 C29 119.1(8) . . ? C23 C28 C29 122.5(5) . . ? N3 C29 O2 114.6(6) . . ? N3 C29 C28 129.7(6) . . ? O2 C29 C28 115.6(6) . . ? O2 C30 C31 103.9(5) . . ? O2 C30 H30A 111.0 . . ? C31 C30 H30A 111.0 . . ? O2 C30 H30B 111.0 . . ? C31 C30 H30B 111.0 . . ? H30A C30 H30B 109.0 . . ? N3 C31 C32 113.3(5) . . ? N3 C31 C30 101.9(5) . . ? C32 C31 C30 113.7(5) . . ? N3 C31 H31 109.2 . . ? C32 C31 H31 109.2 . . ? C30 C31 H31 109.2 . . ? C34 C32 C31 113.4(5) . . ? C34 C32 C33 112.4(5) . . ? C31 C32 C33 110.2(5) . . ? C34 C32 H32 106.8 . . ? C31 C32 H32 106.8 . . ? C33 C32 H32 106.8 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? Cl3 C35 Cl2 112.2(4) . . ? Cl3 C35 Cl1 109.0(4) . . ? Cl2 C35 Cl1 109.8(4) . . ? Cl3 C35 H35 108.6 . . ? Cl2 C35 H35 108.6 . . ? Cl1 C35 H35 108.6 . . ? 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 C22 Ir1 O1 C23 162.5(5) . . . . ? N1 Ir1 O1 C23 -103.3(5) . . . . ? N2 Ir1 O1 C23 82.0(5) . . . . ? N3 Ir1 O1 C23 -11.6(5) . . . . ? C11 Ir1 N1 C1 -177.8(5) . . . . ? C22 Ir1 N1 C1 95.2(4) . . . . ? O1 Ir1 N1 C1 6.0(4) . . . . ? N3 Ir1 N1 C1 -80.1(4) . . . . ? C11 Ir1 N1 C5 4.8(3) . . . . ? C22 Ir1 N1 C5 -82.2(4) . . . . ? O1 Ir1 N1 C5 -171.4(3) . . . . ? N3 Ir1 N1 C5 102.5(4) . . . . ? C11 Ir1 N2 C12 89.1(5) . . . . ? C22 Ir1 N2 C12 176.0(5) . . . . ? O1 Ir1 N2 C12 -95.2(4) . . . . ? N3 Ir1 N2 C12 -9.2(5) . . . . ? C11 Ir1 N2 C16 -86.1(4) . . . . ? C22 Ir1 N2 C16 0.9(4) . . . . ? O1 Ir1 N2 C16 89.6(4) . . . . ? N3 Ir1 N2 C16 175.7(4) . . . . ? C11 Ir1 N3 C29 -175.1(5) . . . . ? N1 Ir1 N3 C29 104.3(5) . . . . ? N2 Ir1 N3 C29 -80.1(5) . . . . ? O1 Ir1 N3 C29 10.8(5) . . . . ? C11 Ir1 N3 C31 -1.7(4) . . . . ? N1 Ir1 N3 C31 -82.3(4) . . . . ? N2 Ir1 N3 C31 93.3(4) . . . . ? O1 Ir1 N3 C31 -175.9(4) . . . . ? C5 N1 C1 C2 -1.3(8) . . . . ? Ir1 N1 C1 C2 -178.6(4) . . . . ? N1 C1 C2 C3 1.2(9) . . . . ? C1 C2 C3 C4 -0.3(9) . . . . ? C2 C3 C4 C5 -0.5(9) . . . . ? C1 N1 C5 C4 0.5(7) . . . . ? Ir1 N1 C5 C4 178.0(4) . . . . ? C1 N1 C5 C6 178.4(5) . . . . ? Ir1 N1 C5 C6 -4.1(5) . . . . ? C3 C4 C5 N1 0.4(8) . . . . ? C3 C4 C5 C6 -177.2(5) . . . . ? N1 C5 C6 C11 0.3(6) . . . . ? C4 C5 C6 C11 178.0(5) . . . . ? N1 C5 C6 C7 -177.2(4) . . . . ? C4 C5 C6 C7 0.6(8) . . . . ? C11 C6 C7 C8 0.2(8) . . . . ? C5 C6 C7 C8 177.5(5) . . . . ? C6 C7 C8 C9 0.1(9) . . . . ? C7 C8 C9 C10 0.4(9) . . . . ? C8 C9 C10 C11 -1.2(9) . . . . ? C7 C6 C11 C10 -1.0(7) . . . . ? C5 C6 C11 C10 -178.5(5) . . . . ? C7 C6 C11 Ir1 -178.8(4) . . . . ? C5 C6 C11 Ir1 3.7(6) . . . . ? C9 C10 C11 C6 1.5(8) . . . . ? C9 C10 C11 Ir1 179.0(4) . . . . ? C22 Ir1 C11 C6 90.2(4) . . . . ? N1 Ir1 C11 C6 -4.5(4) . . . . ? N2 Ir1 C11 C6 170.4(4) . . . . ? N3 Ir1 C11 C6 -95.2(4) . . . . ? C22 Ir1 C11 C10 -87.3(5) . . . . ? N1 Ir1 C11 C10 178.0(5) . . . . ? N2 Ir1 C11 C10 -7.0(5) . . . . ? N3 Ir1 C11 C10 87.4(5) . . . . ? C16 N2 C12 C13 -0.7(8) . . . . ? Ir1 N2 C12 C13 -175.7(4) . . . . ? N2 C12 C13 C14 0.8(9) . . . . ? C12 C13 C14 C15 -1.1(9) . . . . ? C13 C14 C15 C16 1.2(10) . . . . ? C12 N2 C16 C15 0.8(8) . . . . ? Ir1 N2 C16 C15 176.2(4) . . . . ? C12 N2 C16 C17 -178.8(5) . . . . ? Ir1 N2 C16 C17 -3.3(6) . . . . ? C14 C15 C16 N2 -1.1(9) . . . . ? C14 C15 C16 C17 178.4(6) . . . . ? N2 C16 C17 C18 -173.4(5) . . . . ? C15 C16 C17 C18 7.0(9) . . . . ? N2 C16 C17 C22 5.0(7) . . . . ? C15 C16 C17 C22 -174.6(6) . . . . ? C22 C17 C18 C19 3.8(10) . . . . ? C16 C17 C18 C19 -177.9(6) . . . . ? C17 C18 C19 C20 -2.1(10) . . . . ? C18 C19 C20 C21 1.4(10) . . . . ? C19 C20 C21 C22 -2.2(9) . . . . ? C20 C21 C22 C17 3.6(8) . . . . ? C20 C21 C22 Ir1 -174.7(4) . . . . ? C18 C17 C22 C21 -4.4(8) . . . . ? C16 C17 C22 C21 177.2(5) . . . . ? C18 C17 C22 Ir1 174.2(5) . . . . ? C16 C17 C22 Ir1 -4.3(6) . . . . ? C11 Ir1 C22 C21 -84.8(5) . . . . ? N1 Ir1 C22 C21 -4.6(5) . . . . ? N2 Ir1 C22 C21 -179.7(5) . . . . ? O1 Ir1 C22 C21 89.0(5) . . . . ? C11 Ir1 C22 C17 96.9(4) . . . . ? N1 Ir1 C22 C17 177.1(4) . . . . ? N2 Ir1 C22 C17 2.0(4) . . . . ? O1 Ir1 C22 C17 -89.3(4) . . . . ? Ir1 O1 C23 C24 -172.8(4) . . . . ? Ir1 O1 C23 C28 8.2(9) . . . . ? O1 C23 C24 C25 -179.3(6) . . . . ? C28 C23 C24 C25 -0.2(9) . . . . ? C23 C24 C25 C26 0.0(10) . . . . ? C24 C25 C26 C27 0.0(11) . . . . ? C25 C26 C27 C28 0.3(11) . . . . ? C26 C27 C28 C23 -0.5(10) . . . . ? C26 C27 C28 C29 178.0(6) . . . . ? O1 C23 C28 C27 179.4(6) . . . . ? C24 C23 C28 C27 0.5(8) . . . . ? O1 C23 C28 C29 1.0(9) . . . . ? C24 C23 C28 C29 -178.0(6) . . . . ? C31 N3 C29 O2 -2.6(7) . . . . ? Ir1 N3 C29 O2 171.7(4) . . . . ? C31 N3 C29 C28 178.6(6) . . . . ? Ir1 N3 C29 C28 -7.2(9) . . . . ? C30 O2 C29 N3 -8.5(7) . . . . ? C30 O2 C29 C28 170.6(5) . . . . ? C27 C28 C29 N3 -179.8(6) . . . . ? C23 C28 C29 N3 -1.3(10) . . . . ? C27 C28 C29 O2 1.4(8) . . . . ? C23 C28 C29 O2 179.8(5) . . . . ? C29 O2 C30 C31 15.0(6) . . . . ? C29 N3 C31 C32 -111.0(6) . . . . ? Ir1 N3 C31 C32 74.7(6) . . . . ? C29 N3 C31 C30 11.5(6) . . . . ? Ir1 N3 C31 C30 -162.8(4) . . . . ? O2 C30 C31 N3 -15.6(6) . . . . ? O2 C30 C31 C32 106.6(6) . . . . ? N3 C31 C32 C34 59.9(7) . . . . ? C30 C31 C32 C34 -55.8(7) . . . . ? N3 C31 C32 C33 -173.1(5) . . . . ? C30 C31 C32 C33 71.2(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.868 _refine_diff_density_min -0.950 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 922561' ####################################################################### # # 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_09081 #TrackingRef 'Shalini 4 SI.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H28 Ir N5 O, C H3 OH' _chemical_formula_sum 'C34 H32 Ir N5 O2' _chemical_formula_weight 734.85 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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.794(4) _cell_length_b 11.361(5) _cell_length_c 29.429(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2940(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 743 _cell_measurement_theta_min 2.265 _cell_measurement_theta_max 24.142 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 4.582 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.577 _exptl_absorpt_correction_T_max 0.831 _exptl_absorpt_process_details ; absorption correction based on 7138 reflections(SADABS);Rint 0.1889 before correction and 0.0701 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex 2000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23226 _diffrn_reflns_av_R_equivalents 0.1160 _diffrn_reflns_av_sigmaI/netI 0.1155 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5780 _reflns_number_gt 4827 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0061P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(10) _chemical_absolute_configuration ,rm _refine_ls_number_reflns 5780 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0660 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.869 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.94339(4) 0.70199(3) 0.133486(11) 0.01898(8) Uani 1 1 d . . . O1 O 0.8204(6) 0.8078(6) 0.18010(16) 0.0238(13) Uani 1 1 d . . . N1 N 0.7638(7) 0.6923(7) 0.0921(2) 0.0227(15) Uani 1 1 d . . . N2 N 0.7913(7) 0.6453(6) 0.0512(2) 0.0224(17) Uani 1 1 d . . . N3 N 1.1371(7) 0.7199(6) 0.1692(2) 0.0174(16) Uani 1 1 d . . . N4 N 1.2252(7) 0.8135(6) 0.1568(2) 0.0214(16) Uani 1 1 d . . . N5 N 0.8786(7) 0.5507(6) 0.1722(2) 0.0202(17) Uani 1 1 d . . . C1 C 0.6170(8) 0.7233(7) 0.0914(3) 0.025(2) Uani 1 1 d . . . H1 H 0.5638 0.7577 0.1162 0.030 Uiso 1 1 calc R . . C2 C 0.5539(11) 0.6983(8) 0.0494(3) 0.035(2) Uani 1 1 d . . . H2A H 0.4522 0.7130 0.0401 0.042 Uiso 1 1 calc R . . C3 C 0.6669(10) 0.6480(7) 0.0240(3) 0.030(2) Uani 1 1 d . . . H3 H 0.6596 0.6207 -0.0065 0.036 Uiso 1 1 calc R . . C4 C 0.9428(10) 0.5993(6) 0.0441(2) 0.0193(17) Uani 1 1 d . . . C5 C 0.9813(10) 0.5436(7) 0.0035(3) 0.026(2) Uani 1 1 d . . . H5 H 0.9097 0.5353 -0.0205 0.031 Uiso 1 1 calc R . . C6 C 1.1284(10) 0.5007(8) -0.0005(3) 0.030(2) Uani 1 1 d . . . H6 H 1.1598 0.4613 -0.0274 0.036 Uiso 1 1 calc R . . C7 C 1.2281(10) 0.5162(8) 0.0349(3) 0.029(2) Uani 1 1 d . . . H7 H 1.3295 0.4882 0.0322 0.035 Uiso 1 1 calc R . . C8 C 1.1836(10) 0.5715(7) 0.0743(3) 0.027(2) Uani 1 1 d . . . H8 H 1.2566 0.5809 0.0978 0.032 Uiso 1 1 calc R . . C9 C 1.0370(10) 0.6145(7) 0.0816(2) 0.0200(19) Uani 1 1 d . . . C10 C 1.2099(10) 0.6653(7) 0.2020(3) 0.030(2) Uani 1 1 d . . . H10 H 1.1732 0.5972 0.2173 0.036 Uiso 1 1 calc R . . C11 C 1.3476(9) 0.7201(8) 0.2116(3) 0.028(2) Uani 1 1 d . . . H11 H 1.4213 0.6976 0.2335 0.034 Uiso 1 1 calc R . . C12 C 1.3536(9) 0.8146(8) 0.1821(3) 0.025(2) Uani 1 1 d . . . H12 H 1.4337 0.8704 0.1800 0.030 Uiso 1 1 calc R . . C13 C 1.1652(9) 0.8857(7) 0.1228(2) 0.0186(19) Uani 1 1 d . . . C14 C 1.2411(10) 0.9879(8) 0.1095(3) 0.025(2) Uani 1 1 d . . . H14 H 1.3391 1.0059 0.1212 0.030 Uiso 1 1 calc R . . C15 C 1.1694(11) 1.0630(8) 0.0786(3) 0.031(2) Uani 1 1 d . . . H15 H 1.2173 1.1338 0.0692 0.038 Uiso 1 1 calc R . . C16 C 1.0283(10) 1.0325(7) 0.0621(3) 0.024(2) Uani 1 1 d . . . H16 H 0.9779 1.0841 0.0416 0.028 Uiso 1 1 calc R . . C17 C 0.9598(10) 0.9299(7) 0.0745(3) 0.028(2) Uani 1 1 d . . . H17 H 0.8653 0.9099 0.0609 0.034 Uiso 1 1 calc R . . C18 C 1.0231(8) 0.8517(6) 0.1067(2) 0.0160(19) Uani 1 1 d . . . C19 C 0.7693(8) 0.7771(7) 0.2203(3) 0.020(2) Uani 1 1 d . . . C20 C 0.7078(9) 0.8646(8) 0.2483(3) 0.029(2) Uani 1 1 d . . . H20 H 0.7017 0.9430 0.2372 0.034 Uiso 1 1 calc R . . C21 C 0.6558(10) 0.8403(8) 0.2914(3) 0.036(3) Uani 1 1 d . . . H21 H 0.6153 0.9021 0.3094 0.043 Uiso 1 1 calc R . . C22 C 0.6615(11) 0.7285(9) 0.3087(3) 0.042(3) Uani 1 1 d . . . H22 H 0.6272 0.7126 0.3387 0.050 Uiso 1 1 calc R . . C23 C 0.7184(10) 0.6394(9) 0.2815(3) 0.038(3) Uani 1 1 d . . . H23 H 0.7212 0.5615 0.2933 0.046 Uiso 1 1 calc R . . C24 C 0.7725(10) 0.6598(8) 0.2371(3) 0.027(2) Uani 1 1 d . . . C25 C 0.8227(10) 0.5570(7) 0.2113(3) 0.026(2) Uani 1 1 d . . . H25 H 0.8111 0.4838 0.2265 0.032 Uiso 1 1 calc R . . C26 C 0.9149(9) 0.4322(7) 0.1533(3) 0.022(2) Uani 1 1 d . . . H26 H 1.0161 0.4389 0.1380 0.027 Uiso 1 1 calc R . . C27 C 0.9286(10) 0.3320(6) 0.1887(3) 0.028(2) Uani 1 1 d . . . H27A H 0.9957 0.3571 0.2134 0.043 Uiso 1 1 calc R . . H27B H 0.9711 0.2618 0.1741 0.043 Uiso 1 1 calc R . . H27C H 0.8278 0.3137 0.2009 0.043 Uiso 1 1 calc R . . C28 C 0.8039(9) 0.3962(7) 0.1177(3) 0.0209(19) Uani 1 1 d . . . C29 C 0.6488(9) 0.4151(7) 0.1242(3) 0.025(2) Uani 1 1 d . . . H29 H 0.6133 0.4570 0.1501 0.030 Uiso 1 1 calc R . . C30 C 0.5465(11) 0.3713(7) 0.0922(3) 0.032(2) Uani 1 1 d . . . H30 H 0.4407 0.3836 0.0966 0.039 Uiso 1 1 calc R . . C31 C 0.5941(10) 0.3112(9) 0.0546(3) 0.037(2) Uani 1 1 d . . . H31 H 0.5226 0.2800 0.0337 0.044 Uiso 1 1 calc R . . C32 C 0.7468(10) 0.2968(9) 0.0478(3) 0.037(2) Uani 1 1 d . . . H32 H 0.7818 0.2581 0.0211 0.045 Uiso 1 1 calc R . . C33 C 0.8509(10) 0.3379(7) 0.0793(3) 0.030(2) Uani 1 1 d . . . H33 H 0.9565 0.3256 0.0743 0.036 Uiso 1 1 calc R . . C34 C 0.7038(11) 0.0901(8) 0.1500(3) 0.051(3) Uani 1 1 d . . . H34A H 0.6826 0.1208 0.1805 0.077 Uiso 1 1 calc R . . H34B H 0.6636 0.1446 0.1272 0.077 Uiso 1 1 calc R . . H34C H 0.8139 0.0819 0.1460 0.077 Uiso 1 1 calc R . . O2 O 0.6342(6) -0.0202(5) 0.1449(2) 0.0382(18) Uani 1 1 d . . . H2 H 0.7005 -0.0733 0.1463 0.057 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 0.01867(14) 0.01912(14) 0.01915(14) 0.00012(17) -0.00046(17) -0.00128(17) O1 0.030(3) 0.025(3) 0.017(3) 0.001(3) 0.002(3) 0.002(3) N1 0.024(4) 0.027(4) 0.018(4) -0.002(4) 0.005(3) -0.003(4) N2 0.019(4) 0.030(5) 0.018(4) 0.000(3) -0.004(3) -0.008(3) N3 0.022(4) 0.012(4) 0.018(4) 0.007(3) 0.001(3) -0.008(3) N4 0.020(4) 0.024(4) 0.020(4) -0.002(4) 0.006(3) 0.000(4) N5 0.016(4) 0.025(4) 0.019(4) -0.001(3) -0.002(3) -0.003(3) C1 0.023(5) 0.024(6) 0.028(5) 0.001(4) 0.014(4) -0.005(4) C2 0.026(5) 0.036(5) 0.042(5) 0.004(5) -0.009(5) 0.002(7) C3 0.034(5) 0.029(6) 0.026(5) 0.005(4) -0.017(5) -0.011(5) C4 0.019(4) 0.022(4) 0.017(4) 0.004(3) 0.001(4) 0.006(5) C5 0.039(6) 0.012(5) 0.027(5) 0.004(4) -0.013(4) -0.008(4) C6 0.040(6) 0.022(6) 0.026(5) -0.001(4) 0.010(5) 0.007(5) C7 0.023(5) 0.033(6) 0.030(5) -0.002(5) 0.006(4) 0.007(4) C8 0.025(5) 0.020(5) 0.036(6) -0.004(4) 0.005(4) 0.003(4) C9 0.024(5) 0.022(5) 0.014(4) 0.000(3) -0.005(4) -0.011(4) C10 0.042(6) 0.018(5) 0.031(5) 0.009(4) 0.005(5) 0.004(4) C11 0.019(5) 0.032(6) 0.033(5) -0.008(5) -0.009(4) -0.001(4) C12 0.020(5) 0.020(6) 0.035(5) -0.006(4) 0.000(4) -0.005(4) C13 0.027(5) 0.016(4) 0.013(5) -0.003(3) 0.002(4) 0.005(4) C14 0.026(5) 0.029(5) 0.020(5) -0.014(4) 0.002(4) -0.010(4) C15 0.051(7) 0.024(6) 0.019(5) -0.003(4) 0.005(5) -0.007(5) C16 0.038(6) 0.020(5) 0.012(4) 0.004(4) 0.004(4) 0.004(4) C17 0.024(5) 0.032(5) 0.028(5) -0.005(4) 0.001(5) 0.010(5) C18 0.019(5) 0.012(4) 0.017(4) -0.009(3) -0.003(3) 0.008(3) C19 0.014(4) 0.018(6) 0.029(5) -0.010(4) -0.005(4) -0.004(4) C20 0.027(5) 0.030(6) 0.029(5) -0.006(4) -0.002(4) 0.000(4) C21 0.031(6) 0.047(7) 0.030(6) -0.005(5) 0.005(5) 0.002(5) C22 0.052(7) 0.050(8) 0.023(5) 0.004(5) 0.013(5) -0.003(6) C23 0.043(6) 0.046(7) 0.026(6) 0.012(5) 0.004(5) -0.011(5) C24 0.034(6) 0.026(6) 0.021(5) 0.005(4) -0.003(4) -0.011(4) C25 0.032(5) 0.013(5) 0.034(6) 0.011(4) -0.009(5) -0.008(4) C26 0.018(5) 0.016(4) 0.033(5) -0.010(4) 0.000(4) -0.001(4) C27 0.027(5) 0.017(5) 0.041(5) 0.002(4) -0.010(5) 0.000(4) C28 0.027(5) 0.016(5) 0.020(5) 0.006(4) 0.003(4) 0.001(4) C29 0.030(5) 0.026(5) 0.019(5) 0.006(4) -0.002(4) 0.002(4) C30 0.025(5) 0.028(5) 0.044(6) 0.008(4) -0.004(5) 0.001(5) C31 0.040(6) 0.040(6) 0.031(5) -0.001(5) -0.014(4) -0.014(5) C32 0.049(6) 0.027(5) 0.036(6) -0.002(6) 0.003(5) 0.004(6) C33 0.029(5) 0.032(6) 0.028(5) -0.002(4) 0.005(4) 0.003(4) C34 0.060(7) 0.025(6) 0.070(8) 0.005(5) 0.015(6) 0.003(5) O2 0.030(4) 0.031(4) 0.053(5) 0.004(4) -0.003(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 N1 1.997(6) . ? Ir1 C9 2.000(8) . ? Ir1 C18 2.001(8) . ? Ir1 N3 2.012(6) . ? Ir1 O1 2.120(5) . ? Ir1 N5 2.139(7) . ? O1 C19 1.311(9) . ? N1 C1 1.338(9) . ? N1 N2 1.339(8) . ? N2 C3 1.357(9) . ? N2 C4 1.446(10) . ? N3 C10 1.315(9) . ? N3 N4 1.366(8) . ? N4 C12 1.353(9) . ? N4 C13 1.396(9) . ? N5 C25 1.255(10) . ? N5 C26 1.491(9) . ? C1 C2 1.384(10) . ? C1 H1 0.9500 . ? C2 C3 1.369(11) . ? C2 H2A 0.9500 . ? C3 H3 0.9500 . ? C4 C9 1.389(10) . ? C4 C5 1.395(10) . ? C5 C6 1.387(10) . ? C5 H5 0.9500 . ? C6 C7 1.374(11) . ? C6 H6 0.9500 . ? C7 C8 1.375(11) . ? C7 H7 0.9500 . ? C8 C9 1.395(11) . ? C8 H8 0.9500 . ? C10 C11 1.390(11) . ? C10 H10 0.9500 . ? C11 C12 1.381(11) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.391(10) . ? C13 C14 1.394(11) . ? C14 C15 1.397(12) . ? C14 H14 0.9500 . ? C15 C16 1.377(12) . ? C15 H15 0.9500 . ? C16 C17 1.363(11) . ? C16 H16 0.9500 . ? C17 C18 1.414(10) . ? C17 H17 0.9500 . ? C19 C20 1.399(11) . ? C19 C24 1.423(11) . ? C20 C21 1.377(11) . ? C20 H20 0.9500 . ? C21 C22 1.369(11) . ? C21 H21 0.9500 . ? C22 C23 1.385(12) . ? C22 H22 0.9500 . ? C23 C24 1.411(11) . ? C23 H23 0.9500 . ? C24 C25 1.461(11) . ? C25 H25 0.9500 . ? C26 C28 1.488(10) . ? C26 C27 1.547(10) . ? C26 H26 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C33 1.375(10) . ? C28 C29 1.394(10) . ? C29 C30 1.395(11) . ? C29 H29 0.9500 . ? C30 C31 1.364(11) . ? C30 H30 0.9500 . ? C31 C32 1.368(11) . ? C31 H31 0.9500 . ? C32 C33 1.384(11) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 O2 1.403(9) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O2 H2 0.8400 . ? 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 C9 80.4(3) . . ? N1 Ir1 C18 94.8(3) . . ? C9 Ir1 C18 88.7(3) . . ? N1 Ir1 N3 173.5(3) . . ? C9 Ir1 N3 95.8(3) . . ? C18 Ir1 N3 79.8(3) . . ? N1 Ir1 O1 91.3(2) . . ? C9 Ir1 O1 170.4(3) . . ? C18 Ir1 O1 87.2(3) . . ? N3 Ir1 O1 92.1(2) . . ? N1 Ir1 N5 94.0(3) . . ? C9 Ir1 N5 96.7(3) . . ? C18 Ir1 N5 170.3(3) . . ? N3 Ir1 N5 91.6(2) . . ? O1 Ir1 N5 88.6(3) . . ? C19 O1 Ir1 127.4(6) . . ? C1 N1 N2 105.4(6) . . ? C1 N1 Ir1 139.3(6) . . ? N2 N1 Ir1 115.3(5) . . ? N1 N2 C3 112.1(7) . . ? N1 N2 C4 116.1(6) . . ? C3 N2 C4 131.7(7) . . ? C10 N3 N4 106.8(6) . . ? C10 N3 Ir1 138.5(6) . . ? N4 N3 Ir1 114.8(5) . . ? C12 N4 N3 109.4(7) . . ? C12 N4 C13 134.8(8) . . ? N3 N4 C13 115.8(6) . . ? C25 N5 C26 118.5(7) . . ? C25 N5 Ir1 123.2(6) . . ? C26 N5 Ir1 118.1(5) . . ? N1 C1 C2 110.3(7) . . ? N1 C1 H1 124.9 . . ? C2 C1 H1 124.9 . . ? C3 C2 C1 106.5(8) . . ? C3 C2 H2A 126.8 . . ? C1 C2 H2A 126.8 . . ? N2 C3 C2 105.7(8) . . ? N2 C3 H3 127.1 . . ? C2 C3 H3 127.1 . . ? C9 C4 C5 126.3(8) . . ? C9 C4 N2 112.9(7) . . ? C5 C4 N2 120.7(7) . . ? C6 C5 C4 117.3(8) . . ? C6 C5 H5 121.4 . . ? C4 C5 H5 121.4 . . ? C7 C6 C5 119.1(8) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C7 C8 121.1(8) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C9 123.5(8) . . ? C7 C8 H8 118.3 . . ? C9 C8 H8 118.3 . . ? C4 C9 C8 112.7(7) . . ? C4 C9 Ir1 115.0(6) . . ? C8 C9 Ir1 132.2(6) . . ? N3 C10 C11 111.1(8) . . ? N3 C10 H10 124.4 . . ? C11 C10 H10 124.4 . . ? C12 C11 C10 104.8(7) . . ? C12 C11 H11 127.6 . . ? C10 C11 H11 127.6 . . ? N4 C12 C11 107.9(7) . . ? N4 C12 H12 126.0 . . ? C11 C12 H12 126.0 . . ? C18 C13 C14 124.5(8) . . ? C18 C13 N4 114.8(7) . . ? C14 C13 N4 120.5(8) . . ? C13 C14 C15 118.3(8) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C16 C15 C14 118.9(9) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C17 C16 C15 121.2(8) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 122.9(8) . . ? C16 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C13 C18 C17 114.0(7) . . ? C13 C18 Ir1 114.7(6) . . ? C17 C18 Ir1 131.3(6) . . ? O1 C19 C20 118.3(8) . . ? O1 C19 C24 123.8(8) . . ? C20 C19 C24 117.9(8) . . ? C21 C20 C19 121.9(9) . . ? C21 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? C22 C21 C20 121.2(9) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 118.4(9) . . ? C21 C22 H22 120.8 . . ? C23 C22 H22 120.8 . . ? C22 C23 C24 122.5(9) . . ? C22 C23 H23 118.8 . . ? C24 C23 H23 118.8 . . ? C23 C24 C19 118.1(8) . . ? C23 C24 C25 116.9(8) . . ? C19 C24 C25 125.0(8) . . ? N5 C25 C24 129.9(8) . . ? N5 C25 H25 115.1 . . ? C24 C25 H25 115.1 . . ? C28 C26 N5 111.7(6) . . ? C28 C26 C27 108.8(6) . . ? N5 C26 C27 115.5(6) . . ? C28 C26 H26 106.8 . . ? N5 C26 H26 106.8 . . ? C27 C26 H26 106.8 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C33 C28 C29 118.8(8) . . ? C33 C28 C26 120.9(7) . . ? C29 C28 C26 120.2(7) . . ? C28 C29 C30 118.9(8) . . ? C28 C29 H29 120.5 . . ? C30 C29 H29 120.5 . . ? C31 C30 C29 121.8(9) . . ? C31 C30 H30 119.1 . . ? C29 C30 H30 119.1 . . ? C30 C31 C32 118.7(9) . . ? C30 C31 H31 120.6 . . ? C32 C31 H31 120.6 . . ? C31 C32 C33 120.7(9) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C28 C33 C32 121.0(8) . . ? C28 C33 H33 119.5 . . ? C32 C33 H33 119.5 . . ? O2 C34 H34A 109.5 . . ? O2 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O2 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C34 O2 H2 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 N1 Ir1 O1 C19 108.4(6) . . . . ? C18 Ir1 O1 C19 -156.9(6) . . . . ? N3 Ir1 O1 C19 -77.2(6) . . . . ? N5 Ir1 O1 C19 14.4(6) . . . . ? C9 Ir1 N1 C1 178.2(10) . . . . ? C18 Ir1 N1 C1 -93.9(10) . . . . ? O1 Ir1 N1 C1 -6.6(10) . . . . ? N5 Ir1 N1 C1 82.1(10) . . . . ? C9 Ir1 N1 N2 -5.2(6) . . . . ? C18 Ir1 N1 N2 82.7(6) . . . . ? O1 Ir1 N1 N2 170.0(6) . . . . ? N5 Ir1 N1 N2 -101.3(6) . . . . ? C1 N1 N2 C3 1.5(9) . . . . ? Ir1 N1 N2 C3 -176.2(5) . . . . ? C1 N1 N2 C4 -177.2(7) . . . . ? Ir1 N1 N2 C4 5.0(9) . . . . ? C9 Ir1 N3 C10 -94.5(9) . . . . ? C18 Ir1 N3 C10 177.9(9) . . . . ? O1 Ir1 N3 C10 91.1(9) . . . . ? N5 Ir1 N3 C10 2.4(9) . . . . ? C9 Ir1 N3 N4 84.1(5) . . . . ? C18 Ir1 N3 N4 -3.5(5) . . . . ? O1 Ir1 N3 N4 -90.3(5) . . . . ? N5 Ir1 N3 N4 -179.0(5) . . . . ? C10 N3 N4 C12 0.8(9) . . . . ? Ir1 N3 N4 C12 -178.3(5) . . . . ? C10 N3 N4 C13 -178.2(6) . . . . ? Ir1 N3 N4 C13 2.7(8) . . . . ? N1 Ir1 N5 C25 -104.9(7) . . . . ? C9 Ir1 N5 C25 174.4(7) . . . . ? N3 Ir1 N5 C25 78.4(7) . . . . ? O1 Ir1 N5 C25 -13.7(7) . . . . ? N1 Ir1 N5 C26 80.8(5) . . . . ? C9 Ir1 N5 C26 0.1(6) . . . . ? N3 Ir1 N5 C26 -95.9(5) . . . . ? O1 Ir1 N5 C26 172.0(5) . . . . ? N2 N1 C1 C2 -1.5(10) . . . . ? Ir1 N1 C1 C2 175.3(7) . . . . ? N1 C1 C2 C3 1.1(10) . . . . ? N1 N2 C3 C2 -0.8(10) . . . . ? C4 N2 C3 C2 177.6(8) . . . . ? C1 C2 C3 N2 -0.2(10) . . . . ? N1 N2 C4 C9 -1.3(10) . . . . ? C3 N2 C4 C9 -179.7(8) . . . . ? N1 N2 C4 C5 177.0(7) . . . . ? C3 N2 C4 C5 -1.4(13) . . . . ? C9 C4 C5 C6 -1.2(12) . . . . ? N2 C4 C5 C6 -179.3(7) . . . . ? C4 C5 C6 C7 -0.8(12) . . . . ? C5 C6 C7 C8 1.0(13) . . . . ? C6 C7 C8 C9 0.6(14) . . . . ? C5 C4 C9 C8 2.7(12) . . . . ? N2 C4 C9 C8 -179.1(7) . . . . ? C5 C4 C9 Ir1 178.8(6) . . . . ? N2 C4 C9 Ir1 -3.0(9) . . . . ? C7 C8 C9 C4 -2.3(12) . . . . ? C7 C8 C9 Ir1 -177.5(7) . . . . ? N1 Ir1 C9 C4 4.4(6) . . . . ? C18 Ir1 C9 C4 -90.7(6) . . . . ? N3 Ir1 C9 C4 -170.3(6) . . . . ? N5 Ir1 C9 C4 97.3(6) . . . . ? N1 Ir1 C9 C8 179.6(9) . . . . ? C18 Ir1 C9 C8 84.5(8) . . . . ? N3 Ir1 C9 C8 4.8(8) . . . . ? N5 Ir1 C9 C8 -87.5(8) . . . . ? N4 N3 C10 C11 -0.9(9) . . . . ? Ir1 N3 C10 C11 177.8(6) . . . . ? N3 C10 C11 C12 0.7(10) . . . . ? N3 N4 C12 C11 -0.4(9) . . . . ? C13 N4 C12 C11 178.4(8) . . . . ? C10 C11 C12 N4 -0.2(9) . . . . ? C12 N4 C13 C18 -178.2(8) . . . . ? N3 N4 C13 C18 0.5(9) . . . . ? C12 N4 C13 C14 -2.7(13) . . . . ? N3 N4 C13 C14 175.9(7) . . . . ? C18 C13 C14 C15 1.2(12) . . . . ? N4 C13 C14 C15 -173.9(7) . . . . ? C13 C14 C15 C16 -0.9(12) . . . . ? C14 C15 C16 C17 -1.5(13) . . . . ? C15 C16 C17 C18 3.7(13) . . . . ? C14 C13 C18 C17 0.8(11) . . . . ? N4 C13 C18 C17 176.1(6) . . . . ? C14 C13 C18 Ir1 -178.7(6) . . . . ? N4 C13 C18 Ir1 -3.5(8) . . . . ? C16 C17 C18 C13 -3.3(11) . . . . ? C16 C17 C18 Ir1 176.2(6) . . . . ? N1 Ir1 C18 C13 -172.5(5) . . . . ? C9 Ir1 C18 C13 -92.3(6) . . . . ? N3 Ir1 C18 C13 3.8(5) . . . . ? O1 Ir1 C18 C13 96.4(5) . . . . ? N1 Ir1 C18 C17 8.0(7) . . . . ? C9 Ir1 C18 C17 88.2(7) . . . . ? N3 Ir1 C18 C17 -175.7(7) . . . . ? O1 Ir1 C18 C17 -83.1(7) . . . . ? Ir1 O1 C19 C20 171.9(5) . . . . ? Ir1 O1 C19 C24 -8.2(11) . . . . ? O1 C19 C20 C21 -178.1(7) . . . . ? C24 C19 C20 C21 2.0(13) . . . . ? C19 C20 C21 C22 -0.3(14) . . . . ? C20 C21 C22 C23 -1.2(15) . . . . ? C21 C22 C23 C24 0.9(15) . . . . ? C22 C23 C24 C19 0.8(14) . . . . ? C22 C23 C24 C25 -177.1(9) . . . . ? O1 C19 C24 C23 177.9(7) . . . . ? C20 C19 C24 C23 -2.2(12) . . . . ? O1 C19 C24 C25 -4.4(14) . . . . ? C20 C19 C24 C25 175.5(8) . . . . ? C26 N5 C25 C24 -177.8(8) . . . . ? Ir1 N5 C25 C24 7.9(13) . . . . ? C23 C24 C25 N5 -177.9(9) . . . . ? C19 C24 C25 N5 4.4(16) . . . . ? C25 N5 C26 C28 106.2(8) . . . . ? Ir1 N5 C26 C28 -79.2(7) . . . . ? C25 N5 C26 C27 -18.9(11) . . . . ? Ir1 N5 C26 C27 155.7(5) . . . . ? N5 C26 C28 C33 140.6(8) . . . . ? C27 C26 C28 C33 -90.7(9) . . . . ? N5 C26 C28 C29 -43.3(10) . . . . ? C27 C26 C28 C29 85.4(9) . . . . ? C33 C28 C29 C30 1.7(12) . . . . ? C26 C28 C29 C30 -174.4(7) . . . . ? C28 C29 C30 C31 -0.3(13) . . . . ? C29 C30 C31 C32 -1.9(14) . . . . ? C30 C31 C32 C33 2.7(15) . . . . ? C29 C28 C33 C32 -1.0(13) . . . . ? C26 C28 C33 C32 175.2(8) . . . . ? C31 C32 C33 C28 -1.3(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1 0.84 1.98 2.752(8) 151.9 1_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.230 _refine_diff_density_min -1.048 _refine_diff_density_rms 0.144 _database_code_depnum_ccdc_archive 'CCDC 922562' ####################################################################### # # 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_09065 #TrackingRef 'Shalini_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 Ir N5 O2, 0.5 C6 H14' _chemical_formula_sum 'C33 H35 Ir N5 O2' _chemical_formula_weight 725.86 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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(5) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 19.805(7) _cell_length_b 19.805(7) _cell_length_c 12.370(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4202(3) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 953 _cell_measurement_theta_min 2.635 _cell_measurement_theta_max 24.054 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2166 _exptl_absorpt_coefficient_mu 4.807 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.506 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details ; absorption correction based on 19593 reflections(SADABS);Rint 0.1125 before correction and 0.0551 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex 2000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35447 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0551 _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 -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6093 _reflns_number_gt 5521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Disordered C6H14 was omitted using the SQUEEZE option of PLATON. The solvent accessible voids are 268.9 3 with an estimated 118e/cell to be added. Three solvent C6H14 molecules/unit cell accounting for 150e were included in the formula, FWt, (000) and density calculations. PLATON Reference: Spek, A.L. (1990), Acta Cryst. A46, C-34. 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^)+(0.0232P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(7) _chemical_absolute_configuration ,rm _refine_ls_number_reflns 6093 _refine_ls_number_parameters 345 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0595 _refine_ls_wR_factor_gt 0.0586 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.438420(11) 0.345169(11) 0.03100(2) 0.01987(5) Uani 1 1 d . . . O1 O 0.4174(2) 0.3635(2) -0.1325(3) 0.0297(8) Uani 1 1 d . . . O2 O 0.1989(2) 0.1730(2) -0.0168(3) 0.0324(10) Uani 1 1 d . . . N1 N 0.4240(2) 0.4322(2) 0.0903(3) 0.0214(10) Uani 1 1 d . . . N2 N 0.4437(2) 0.4492(2) 0.1961(4) 0.0221(9) Uani 1 1 d . . . N3 N 0.4612(3) 0.2612(3) -0.0193(4) 0.0252(10) Uani 1 1 d . . . N4 N 0.5364(3) 0.2857(3) -0.0398(4) 0.0300(11) Uani 1 1 d . . . N5 N 0.3166(2) 0.2647(2) 0.0396(4) 0.0241(10) Uani 1 1 d . . . C1 C 0.3993(3) 0.4802(3) 0.0561(5) 0.0271(13) Uani 1 1 d . . . H1 H 0.3826 0.4819 -0.0153 0.033 Uiso 1 1 calc R . . C2 C 0.4021(3) 0.5273(3) 0.1419(5) 0.0263(13) Uani 1 1 d . . . H2 H 0.3875 0.5662 0.1402 0.032 Uiso 1 1 calc R . . C3 C 0.4298(3) 0.5062(3) 0.2285(4) 0.0252(13) Uani 1 1 d . . . H3 H 0.4379 0.5278 0.2991 0.030 Uiso 1 1 calc R . . C4 C 0.4630(3) 0.3984(3) 0.2519(4) 0.0213(12) Uani 1 1 d . . . C5 C 0.4770(3) 0.4050(3) 0.3612(5) 0.0274(11) Uani 1 1 d . . . H5 H 0.4771 0.4461 0.4012 0.033 Uiso 1 1 calc R . . C6 C 0.4909(3) 0.3505(3) 0.4124(5) 0.0315(14) Uani 1 1 d . . . H6 H 0.5008 0.3539 0.4879 0.038 Uiso 1 1 calc R . . C7 C 0.4899(3) 0.2913(3) 0.3516(5) 0.0275(12) Uani 1 1 d . . . H7 H 0.4985 0.2534 0.3861 0.033 Uiso 1 1 calc R . . C8 C 0.4768(3) 0.2864(3) 0.2418(4) 0.0239(12) Uani 1 1 d . . . H8 H 0.4779 0.2460 0.2020 0.029 Uiso 1 1 calc R . . C9 C 0.4617(3) 0.3394(3) 0.1873(4) 0.0194(10) Uani 1 1 d . . . C10 C 0.4230(3) 0.1842(3) -0.0285(4) 0.0293(13) Uani 1 1 d . . . H10 H 0.3685 0.1515 -0.0183 0.035 Uiso 1 1 calc R . . C11 C 0.4743(4) 0.1584(4) -0.0550(5) 0.0349(15) Uani 1 1 d . . . H11 H 0.4620 0.1059 -0.0655 0.042 Uiso 1 1 calc R . . C12 C 0.5455(4) 0.2231(4) -0.0631(5) 0.0374(16) Uani 1 1 d . . . H12 H 0.5929 0.2248 -0.0815 0.045 Uiso 1 1 calc R . . C13 C 0.5887(3) 0.3677(3) -0.0278(4) 0.0297(13) Uani 1 1 d . . . C14 C 0.6684(4) 0.4007(4) -0.0496(6) 0.0460(18) Uani 1 1 d . . . H14 H 0.6892 0.3694 -0.0746 0.055 Uiso 1 1 calc R . . C15 C 0.7153(4) 0.4785(4) -0.0340(5) 0.0486(19) Uani 1 1 d . . . H15 H 0.7695 0.5021 -0.0488 0.058 Uiso 1 1 calc R . . C16 C 0.6850(3) 0.5238(4) 0.0031(4) 0.0382(16) Uani 1 1 d . . . H16 H 0.7183 0.5781 0.0149 0.046 Uiso 1 1 calc R . . C17 C 0.6057(3) 0.4895(3) 0.0230(5) 0.0290(12) Uani 1 1 d . . . H17 H 0.5852 0.5210 0.0481 0.035 Uiso 1 1 calc R . . C18 C 0.5553(3) 0.4100(3) 0.0072(4) 0.0233(12) Uani 1 1 d . . . C19 C 0.3597(4) 0.3154(3) -0.1927(5) 0.0299(14) Uani 1 1 d . . . C20 C 0.3672(4) 0.3278(3) -0.3060(5) 0.0401(14) Uani 1 1 d . . . H20 H 0.4150 0.3689 -0.3335 0.048 Uiso 1 1 calc R . . C21 C 0.3098(5) 0.2839(5) -0.3767(6) 0.060(2) Uani 1 1 d . . . H21 H 0.3178 0.2943 -0.4520 0.072 Uiso 1 1 calc R . . C22 C 0.2387(5) 0.2230(5) -0.3390(6) 0.072(3) Uani 1 1 d . . . H22 H 0.1978 0.1929 -0.3884 0.086 Uiso 1 1 calc R . . C23 C 0.2283(4) 0.2070(5) -0.2301(6) 0.061(2) Uani 1 1 d . . . H23 H 0.1806 0.1645 -0.2050 0.073 Uiso 1 1 calc R . . C24 C 0.2872(3) 0.2528(3) -0.1556(5) 0.0290(13) Uani 1 1 d . . . C25 C 0.2710(3) 0.2337(3) -0.0413(5) 0.0269(13) Uani 1 1 d . . . C26 C 0.2002(4) 0.1555(4) 0.0965(5) 0.0351(15) Uani 1 1 d . . . H26A H 0.2035 0.1076 0.1057 0.042 Uiso 1 1 calc R . . H26B H 0.1530 0.1486 0.1340 0.042 Uiso 1 1 calc R . . C27 C 0.2742(3) 0.2276(3) 0.1400(5) 0.0266(13) Uani 1 1 d . . . H27 H 0.3052 0.2097 0.1827 0.032 Uiso 1 1 calc R . . C28 C 0.2589(3) 0.2816(3) 0.2099(5) 0.0259(12) Uani 1 1 d . . . H28 H 0.3101 0.3297 0.2241 0.031 Uiso 1 1 calc R . . C29 C 0.2241(4) 0.2442(4) 0.3184(5) 0.0468(18) Uani 1 1 d . . . H29A H 0.1734 0.1972 0.3068 0.070 Uiso 1 1 calc R . . H29B H 0.2173 0.2812 0.3633 0.070 Uiso 1 1 calc R . . H29C H 0.2592 0.2301 0.3550 0.070 Uiso 1 1 calc R . . C30 C 0.2065(4) 0.3063(4) 0.1534(5) 0.0456(18) Uani 1 1 d . . . H30A H 0.2278 0.3272 0.0818 0.068 Uiso 1 1 calc R . . H30B H 0.2038 0.3464 0.1964 0.068 Uiso 1 1 calc R . . H30C H 0.1540 0.2610 0.1456 0.068 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 0.01984(11) 0.02267(11) 0.01840(9) -0.00095(9) -0.00177(9) 0.01161(9) O1 0.033(2) 0.033(2) 0.0177(19) -0.001(2) -0.002(2) 0.0120(18) O2 0.025(2) 0.029(2) 0.036(2) -0.0041(18) -0.0058(18) 0.0077(19) N1 0.023(2) 0.019(2) 0.022(2) 0.0006(18) 0.0006(19) 0.010(2) N2 0.025(2) 0.022(2) 0.018(2) 0.000(2) -0.001(2) 0.0116(18) N3 0.029(3) 0.031(3) 0.023(2) -0.003(2) 0.001(2) 0.020(2) N4 0.023(3) 0.040(3) 0.028(3) -0.006(2) 0.003(2) 0.016(2) N5 0.022(2) 0.022(2) 0.027(3) -0.004(2) -0.007(2) 0.0105(19) C1 0.022(3) 0.027(3) 0.034(4) 0.007(2) 0.001(2) 0.014(2) C2 0.032(3) 0.023(3) 0.031(3) 0.000(2) 0.003(3) 0.018(3) C3 0.031(3) 0.021(3) 0.029(3) 0.002(2) 0.006(2) 0.016(3) C4 0.019(3) 0.018(3) 0.026(3) 0.002(2) -0.001(2) 0.009(2) C5 0.029(3) 0.031(3) 0.025(3) -0.006(3) -0.005(3) 0.017(2) C6 0.028(3) 0.037(3) 0.023(3) 0.003(3) -0.005(2) 0.012(3) C7 0.032(3) 0.026(3) 0.025(3) 0.004(3) -0.005(3) 0.015(2) C8 0.022(3) 0.024(3) 0.026(3) -0.003(2) 0.001(2) 0.012(2) C9 0.019(2) 0.027(3) 0.013(3) 0.002(2) -0.001(2) 0.011(2) C10 0.033(3) 0.031(3) 0.022(3) -0.008(3) -0.007(2) 0.015(3) C11 0.050(4) 0.037(4) 0.031(3) -0.009(3) -0.007(3) 0.032(3) C12 0.040(4) 0.050(4) 0.035(4) -0.011(3) -0.001(3) 0.032(3) C13 0.024(3) 0.039(4) 0.025(3) -0.005(3) 0.000(2) 0.015(3) C14 0.030(4) 0.055(5) 0.054(4) -0.016(4) 0.000(3) 0.022(3) C15 0.021(3) 0.064(5) 0.046(4) -0.007(4) 0.011(3) 0.011(3) C16 0.029(3) 0.043(4) 0.024(4) 0.000(3) 0.001(2) 0.004(3) C17 0.028(3) 0.034(3) 0.023(3) 0.004(3) -0.002(3) 0.014(2) C18 0.019(3) 0.029(3) 0.020(3) 0.001(2) -0.002(2) 0.011(2) C19 0.034(3) 0.036(4) 0.028(3) -0.006(3) -0.007(3) 0.025(3) C20 0.043(4) 0.052(4) 0.024(3) 0.002(3) -0.002(3) 0.023(3) C21 0.065(5) 0.069(5) 0.027(4) -0.006(4) -0.007(4) 0.020(5) C22 0.047(5) 0.095(7) 0.030(4) -0.016(4) -0.023(3) 0.002(5) C23 0.040(5) 0.073(6) 0.038(4) -0.010(4) -0.005(4) 0.004(4) C24 0.029(3) 0.035(3) 0.027(4) -0.004(3) -0.006(3) 0.018(3) C25 0.026(3) 0.026(3) 0.031(3) 0.000(3) -0.004(3) 0.015(3) C26 0.041(4) 0.027(3) 0.034(4) 0.001(3) 0.000(3) 0.014(3) C27 0.019(3) 0.020(3) 0.037(4) 0.009(3) 0.000(3) 0.007(2) C28 0.018(3) 0.024(3) 0.032(3) -0.002(3) -0.004(3) 0.008(2) C29 0.055(5) 0.061(5) 0.034(4) 0.001(3) 0.005(3) 0.036(4) C30 0.052(4) 0.052(4) 0.048(4) 0.005(3) 0.007(3) 0.038(4) _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 C9 2.004(6) . ? Ir1 N1 2.022(4) . ? Ir1 N3 2.026(4) . ? Ir1 C18 2.030(5) . ? Ir1 N5 2.128(4) . ? Ir1 O1 2.132(4) . ? O1 C19 1.297(6) . ? O2 C25 1.362(7) . ? O2 C26 1.448(7) . ? N1 C1 1.335(6) . ? N1 N2 1.359(6) . ? N2 C3 1.351(6) . ? N2 C4 1.422(6) . ? N3 C10 1.326(7) . ? N3 N4 1.340(6) . ? N4 C12 1.370(7) . ? N4 C13 1.432(7) . ? N5 C25 1.281(7) . ? N5 C27 1.474(7) . ? C1 C2 1.397(7) . ? C1 H1 0.9500 . ? C2 C3 1.359(7) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C5 1.373(8) . ? C4 C9 1.405(7) . ? C5 C6 1.393(7) . ? C5 H5 0.9500 . ? C6 C7 1.386(8) . ? C6 H6 0.9500 . ? C7 C8 1.377(8) . ? C7 H7 0.9500 . ? C8 C9 1.399(7) . ? C8 H8 0.9500 . ? C10 C11 1.386(8) . ? C10 H10 0.9500 . ? C11 C12 1.355(9) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.371(7) . ? C13 C14 1.400(8) . ? C14 C15 1.358(9) . ? C14 H14 0.9500 . ? C15 C16 1.384(9) . ? C15 H15 0.9500 . ? C16 C17 1.386(7) . ? C16 H16 0.9500 . ? C17 C18 1.394(7) . ? C17 H17 0.9500 . ? C19 C20 1.418(9) . ? C19 C24 1.424(8) . ? C20 C21 1.351(9) . ? C20 H20 0.9500 . ? C21 C22 1.399(10) . ? C21 H21 0.9500 . ? C22 C23 1.375(10) . ? C22 H22 0.9500 . ? C23 C24 1.405(9) . ? C23 H23 0.9500 . ? C24 C25 1.457(8) . ? C26 C27 1.544(8) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.519(8) . ? C27 H27 1.0000 . ? C28 C30 1.521(8) . ? C28 C29 1.522(8) . ? C28 H28 1.0000 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? 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 C9 Ir1 N1 80.37(19) . . ? C9 Ir1 N3 95.61(19) . . ? N1 Ir1 N3 174.83(18) . . ? C9 Ir1 C18 87.3(2) . . ? N1 Ir1 C18 96.67(19) . . ? N3 Ir1 C18 79.8(2) . . ? C9 Ir1 N5 96.7(2) . . ? N1 Ir1 N5 91.67(17) . . ? N3 Ir1 N5 92.02(17) . . ? C18 Ir1 N5 171.3(2) . . ? C9 Ir1 O1 174.14(18) . . ? N1 Ir1 O1 94.38(16) . . ? N3 Ir1 O1 89.49(16) . . ? C18 Ir1 O1 90.72(17) . . ? N5 Ir1 O1 85.99(16) . . ? C19 O1 Ir1 126.5(4) . . ? C25 O2 C26 106.9(5) . . ? C1 N1 N2 107.0(4) . . ? C1 N1 Ir1 138.5(4) . . ? N2 N1 Ir1 114.5(3) . . ? C3 N2 N1 109.8(4) . . ? C3 N2 C4 133.4(5) . . ? N1 N2 C4 116.0(4) . . ? C10 N3 N4 106.9(5) . . ? C10 N3 Ir1 137.6(4) . . ? N4 N3 Ir1 115.1(3) . . ? N3 N4 C12 109.7(5) . . ? N3 N4 C13 115.7(4) . . ? C12 N4 C13 134.4(5) . . ? C25 N5 C27 109.3(4) . . ? C25 N5 Ir1 125.8(4) . . ? C27 N5 Ir1 124.4(4) . . ? N1 C1 C2 109.1(5) . . ? N1 C1 H1 125.5 . . ? C2 C1 H1 125.5 . . ? C3 C2 C1 106.3(5) . . ? C3 C2 H2 126.8 . . ? C1 C2 H2 126.8 . . ? N2 C3 C2 107.8(5) . . ? N2 C3 H3 126.1 . . ? C2 C3 H3 126.1 . . ? C5 C4 C9 124.0(5) . . ? C5 C4 N2 121.6(5) . . ? C9 C4 N2 114.3(5) . . ? C4 C5 C6 118.8(5) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C7 C6 C5 119.0(5) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C8 C7 C6 121.1(5) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 121.8(5) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C9 C4 115.2(5) . . ? C8 C9 Ir1 130.4(4) . . ? C4 C9 Ir1 114.3(4) . . ? N3 C10 C11 110.1(5) . . ? N3 C10 H10 124.9 . . ? C11 C10 H10 124.9 . . ? C12 C11 C10 106.0(5) . . ? C12 C11 H11 127.0 . . ? C10 C11 H11 127.0 . . ? C11 C12 N4 107.2(6) . . ? C11 C12 H12 126.4 . . ? N4 C12 H12 126.4 . . ? C18 C13 C14 123.5(6) . . ? C18 C13 N4 115.4(5) . . ? C14 C13 N4 121.1(5) . . ? C15 C14 C13 118.2(6) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C14 C15 C16 120.8(6) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C17 119.5(6) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 121.7(6) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C13 C18 C17 116.2(5) . . ? C13 C18 Ir1 113.9(4) . . ? C17 C18 Ir1 129.9(4) . . ? O1 C19 C20 117.5(6) . . ? O1 C19 C24 126.1(5) . . ? C20 C19 C24 116.3(5) . . ? C21 C20 C19 123.1(6) . . ? C21 C20 H20 118.4 . . ? C19 C20 H20 118.4 . . ? C20 C21 C22 120.0(7) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 119.7(7) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 120.9(7) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C23 C24 C19 120.0(6) . . ? C23 C24 C25 117.7(6) . . ? C19 C24 C25 122.3(5) . . ? N5 C25 O2 115.2(5) . . ? N5 C25 C24 128.5(5) . . ? O2 C25 C24 116.3(5) . . ? O2 C26 C27 103.8(5) . . ? O2 C26 H26A 111.0 . . ? C27 C26 H26A 111.0 . . ? O2 C26 H26B 111.0 . . ? C27 C26 H26B 111.0 . . ? H26A C26 H26B 109.0 . . ? N5 C27 C28 113.1(4) . . ? N5 C27 C26 102.0(5) . . ? C28 C27 C26 114.7(5) . . ? N5 C27 H27 108.9 . . ? C28 C27 H27 108.9 . . ? C26 C27 H27 108.9 . . ? C27 C28 C30 111.9(5) . . ? C27 C28 C29 111.1(5) . . ? C30 C28 C29 110.3(5) . . ? C27 C28 H28 107.8 . . ? C30 C28 H28 107.8 . . ? C29 C28 H28 107.8 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 N1 Ir1 O1 C19 -115.2(4) . . . . ? N3 Ir1 O1 C19 68.3(4) . . . . ? C18 Ir1 O1 C19 148.1(5) . . . . ? N5 Ir1 O1 C19 -23.8(4) . . . . ? C9 Ir1 N1 C1 -173.0(6) . . . . ? C18 Ir1 N1 C1 100.8(6) . . . . ? N5 Ir1 N1 C1 -76.5(6) . . . . ? O1 Ir1 N1 C1 9.6(5) . . . . ? C9 Ir1 N1 N2 6.5(3) . . . . ? C18 Ir1 N1 N2 -79.7(3) . . . . ? N5 Ir1 N1 N2 103.0(3) . . . . ? O1 Ir1 N1 N2 -170.9(3) . . . . ? C1 N1 N2 C3 1.4(5) . . . . ? Ir1 N1 N2 C3 -178.2(3) . . . . ? C1 N1 N2 C4 172.9(4) . . . . ? Ir1 N1 N2 C4 -6.7(5) . . . . ? C9 Ir1 N3 C10 86.6(6) . . . . ? C18 Ir1 N3 C10 172.9(6) . . . . ? N5 Ir1 N3 C10 -10.3(6) . . . . ? O1 Ir1 N3 C10 -96.3(6) . . . . ? C9 Ir1 N3 N4 -84.7(4) . . . . ? C18 Ir1 N3 N4 1.6(4) . . . . ? N5 Ir1 N3 N4 178.4(4) . . . . ? O1 Ir1 N3 N4 92.4(4) . . . . ? C10 N3 N4 C12 0.5(6) . . . . ? Ir1 N3 N4 C12 174.4(4) . . . . ? C10 N3 N4 C13 -176.5(5) . . . . ? Ir1 N3 N4 C13 -2.7(6) . . . . ? C9 Ir1 N5 C25 -167.1(4) . . . . ? N1 Ir1 N5 C25 112.4(4) . . . . ? N3 Ir1 N5 C25 -71.2(4) . . . . ? O1 Ir1 N5 C25 18.2(4) . . . . ? C9 Ir1 N5 C27 3.5(4) . . . . ? N1 Ir1 N5 C27 -77.0(4) . . . . ? N3 Ir1 N5 C27 99.4(4) . . . . ? O1 Ir1 N5 C27 -171.3(4) . . . . ? N2 N1 C1 C2 -1.2(6) . . . . ? Ir1 N1 C1 C2 178.3(4) . . . . ? N1 C1 C2 C3 0.5(6) . . . . ? N1 N2 C3 C2 -1.2(6) . . . . ? C4 N2 C3 C2 -170.6(5) . . . . ? C1 C2 C3 N2 0.4(6) . . . . ? C3 N2 C4 C5 -5.0(8) . . . . ? N1 N2 C4 C5 -173.9(5) . . . . ? C3 N2 C4 C9 171.4(5) . . . . ? N1 N2 C4 C9 2.4(6) . . . . ? C9 C4 C5 C6 0.1(8) . . . . ? N2 C4 C5 C6 176.1(5) . . . . ? C4 C5 C6 C7 -0.2(8) . . . . ? C5 C6 C7 C8 1.1(8) . . . . ? C6 C7 C8 C9 -1.8(8) . . . . ? C7 C8 C9 C4 1.6(8) . . . . ? C7 C8 C9 Ir1 -178.5(4) . . . . ? C5 C4 C9 C8 -0.8(8) . . . . ? N2 C4 C9 C8 -177.0(4) . . . . ? C5 C4 C9 Ir1 179.3(4) . . . . ? N2 C4 C9 Ir1 3.1(6) . . . . ? N1 Ir1 C9 C8 175.0(5) . . . . ? N3 Ir1 C9 C8 -8.3(5) . . . . ? C18 Ir1 C9 C8 -87.8(5) . . . . ? N5 Ir1 C9 C8 84.4(5) . . . . ? N1 Ir1 C9 C4 -5.1(4) . . . . ? N3 Ir1 C9 C4 171.6(4) . . . . ? C18 Ir1 C9 C4 92.1(4) . . . . ? N5 Ir1 C9 C4 -95.6(4) . . . . ? N4 N3 C10 C11 0.2(6) . . . . ? Ir1 N3 C10 C11 -171.6(4) . . . . ? N3 C10 C11 C12 -0.8(7) . . . . ? C10 C11 C12 N4 1.0(7) . . . . ? N3 N4 C12 C11 -1.0(7) . . . . ? C13 N4 C12 C11 175.3(6) . . . . ? N3 N4 C13 C18 2.5(7) . . . . ? C12 N4 C13 C18 -173.6(6) . . . . ? N3 N4 C13 C14 -178.4(5) . . . . ? C12 N4 C13 C14 5.5(10) . . . . ? C18 C13 C14 C15 0.8(10) . . . . ? N4 C13 C14 C15 -178.3(6) . . . . ? C13 C14 C15 C16 0.5(11) . . . . ? C14 C15 C16 C17 -1.0(10) . . . . ? C15 C16 C17 C18 0.4(9) . . . . ? C14 C13 C18 C17 -1.3(9) . . . . ? N4 C13 C18 C17 177.8(5) . . . . ? C14 C13 C18 Ir1 179.8(5) . . . . ? N4 C13 C18 Ir1 -1.1(6) . . . . ? C16 C17 C18 C13 0.7(8) . . . . ? C16 C17 C18 Ir1 179.4(4) . . . . ? C9 Ir1 C18 C13 95.9(4) . . . . ? N1 Ir1 C18 C13 175.9(4) . . . . ? N3 Ir1 C18 C13 -0.2(4) . . . . ? O1 Ir1 C18 C13 -89.6(4) . . . . ? C9 Ir1 C18 C17 -82.7(5) . . . . ? N1 Ir1 C18 C17 -2.8(5) . . . . ? N3 Ir1 C18 C17 -178.9(5) . . . . ? O1 Ir1 C18 C17 91.7(5) . . . . ? Ir1 O1 C19 C20 -162.4(4) . . . . ? Ir1 O1 C19 C24 20.6(8) . . . . ? O1 C19 C20 C21 -176.9(6) . . . . ? C24 C19 C20 C21 0.4(9) . . . . ? C19 C20 C21 C22 0.2(12) . . . . ? C20 C21 C22 C23 -1.5(14) . . . . ? C21 C22 C23 C24 2.3(14) . . . . ? C22 C23 C24 C19 -1.7(12) . . . . ? C22 C23 C24 C25 178.2(8) . . . . ? O1 C19 C24 C23 177.3(6) . . . . ? C20 C19 C24 C23 0.3(9) . . . . ? O1 C19 C24 C25 -2.5(9) . . . . ? C20 C19 C24 C25 -179.5(5) . . . . ? C27 N5 C25 O2 -3.9(6) . . . . ? Ir1 N5 C25 O2 167.8(3) . . . . ? C27 N5 C25 C24 178.8(6) . . . . ? Ir1 N5 C25 C24 -9.5(8) . . . . ? C26 O2 C25 N5 -7.6(6) . . . . ? C26 O2 C25 C24 170.1(5) . . . . ? C23 C24 C25 N5 176.6(6) . . . . ? C19 C24 C25 N5 -3.6(9) . . . . ? C23 C24 C25 O2 -0.7(8) . . . . ? C19 C24 C25 O2 179.1(5) . . . . ? C25 O2 C26 C27 14.8(6) . . . . ? C25 N5 C27 C28 -111.1(5) . . . . ? Ir1 N5 C27 C28 77.0(5) . . . . ? C25 N5 C27 C26 12.7(6) . . . . ? Ir1 N5 C27 C26 -159.2(3) . . . . ? O2 C26 C27 N5 -16.3(6) . . . . ? O2 C26 C27 C28 106.4(5) . . . . ? N5 C27 C28 C30 63.2(6) . . . . ? C26 C27 C28 C30 -53.2(6) . . . . ? N5 C27 C28 C29 -173.1(5) . . . . ? C26 C27 C28 C29 70.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.062 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.106 _database_code_depnum_ccdc_archive 'CCDC 922563' ####################################################################### # # 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_09071 #TrackingRef 'Shalini_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 Ir N5 O, H2 O' _chemical_formula_sum 'C30 H30 Ir N5 O3' _chemical_formula_weight 700.79 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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.286(5) _cell_length_b 27.646(16) _cell_length_c 16.326(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.865(10) _cell_angle_gamma 90.00 _cell_volume 4176(4) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 905 _cell_measurement_theta_min 2.439 _cell_measurement_theta_max 23.531 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2076 _exptl_absorpt_coefficient_mu 4.836 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.440 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details ; absorption correction based on 12108 reflections(SADABS);Rint 0.1795 before correction and 0.0726 after. ; _exptl_special_details ; The crystal data was not the best due to crystal quality. The data was not the best to resolve all atoms as anisotropic and one of the atoms (C9A) was refined as isotropic. Some of the other atoms are prolate and oblate. Hydrogen atoms on the waters have been omitted but have been included in all formulae. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex 2000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32410 _diffrn_reflns_av_R_equivalents 0.1149 _diffrn_reflns_av_sigmaI/netI 0.1579 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 26.00 _reflns_number_total 16038 _reflns_number_gt 11778 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.007(10) _chemical_absolute_configuration ,rm _refine_ls_number_reflns 16038 _refine_ls_number_parameters 1055 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 1.02264(6) 0.210001(18) 0.14653(4) 0.02678(14) Uani 1 1 d . . . O1 O 0.9556(11) 0.1469(3) 0.0757(6) 0.032(2) Uani 1 1 d . . . O2 O 0.6473(11) 0.1602(4) 0.2529(7) 0.043(3) Uani 1 1 d . . . N1 N 0.9245(12) 0.2502(4) 0.0556(7) 0.027(3) Uani 1 1 d . . . N2 N 1.0082(13) 0.2629(4) -0.0046(7) 0.032(3) Uani 1 1 d . . . N3 N 1.1379(13) 0.1749(4) 0.2341(7) 0.030(3) Uani 1 1 d . . . N4 N 1.2041(12) 0.1998(4) 0.2958(7) 0.030(3) Uani 1 1 d . . . N5 N 0.8403(13) 0.1979(4) 0.2122(8) 0.031(3) Uani 1 1 d . . . C1 C 0.7956(17) 0.2701(6) 0.0355(10) 0.042(4) Uani 1 1 d . . . H1 H 0.7143 0.2670 0.0667 0.050 Uiso 1 1 calc R . . C2 C 0.796(2) 0.2962(6) -0.0380(11) 0.055(5) Uani 1 1 d . . . H2 H 0.7187 0.3140 -0.0651 0.066 Uiso 1 1 calc R . . C3 C 0.9294(18) 0.2909(6) -0.0619(10) 0.045(4) Uani 1 1 d . . . H3 H 0.9638 0.3041 -0.1103 0.054 Uiso 1 1 calc R . . C4 C 1.1549(15) 0.2476(5) 0.0091(9) 0.028(3) Uani 1 1 d . . . C5 C 1.2531(18) 0.2595(5) -0.0472(9) 0.036(4) Uani 1 1 d . . . H5 H 1.2221 0.2772 -0.0954 0.044 Uiso 1 1 calc R . . C6 C 1.3938(17) 0.2458(5) -0.0333(9) 0.036(4) Uani 1 1 d . . . H6 H 1.4634 0.2539 -0.0705 0.043 Uiso 1 1 calc R . . C7 C 1.4301(15) 0.2201(5) 0.0362(9) 0.028(3) Uani 1 1 d . . . H7 H 1.5280 0.2106 0.0478 0.033 Uiso 1 1 calc R . . C8 C 1.3290(16) 0.2066(5) 0.0922(9) 0.039(4) Uani 1 1 d . . . H8 H 1.3585 0.1883 0.1399 0.047 Uiso 1 1 calc R . . C9 C 1.1853(15) 0.2207(4) 0.0760(9) 0.027(3) Uani 1 1 d . . . C10 C 1.1801(16) 0.1278(5) 0.2498(11) 0.039(4) Uani 1 1 d . . . H10 H 1.1555 0.1006 0.2158 0.047 Uiso 1 1 calc R . . C11 C 1.2655(16) 0.1269(5) 0.3248(10) 0.039(4) Uani 1 1 d . . . H11 H 1.3053 0.0987 0.3513 0.047 Uiso 1 1 calc R . . C12 C 1.2820(17) 0.1727(6) 0.3535(9) 0.038(4) Uani 1 1 d . . . H12 H 1.3355 0.1835 0.4023 0.045 Uiso 1 1 calc R . . C13 C 1.1808(15) 0.2512(5) 0.2894(9) 0.032(4) Uani 1 1 d . . . C14 C 1.2449(18) 0.2824(6) 0.3492(10) 0.044(4) Uani 1 1 d . . . H14 H 1.3028 0.2712 0.3962 0.053 Uiso 1 1 calc R . . C15 C 1.2158(18) 0.3330(5) 0.3338(11) 0.048(5) Uani 1 1 d . . . H15 H 1.2502 0.3564 0.3735 0.057 Uiso 1 1 calc R . . C16 C 1.1383(16) 0.3482(5) 0.2617(10) 0.040(4) Uani 1 1 d . . . H16 H 1.1227 0.3817 0.2511 0.047 Uiso 1 1 calc R . . C17 C 1.0849(15) 0.3142(5) 0.2064(10) 0.035(4) Uani 1 1 d . . . H17 H 1.0338 0.3249 0.1569 0.042 Uiso 1 1 calc R . . C18 C 1.1014(15) 0.2646(5) 0.2190(9) 0.030(4) Uani 1 1 d . . . C19 C 0.8247(16) 0.1273(5) 0.0709(10) 0.032(4) Uani 1 1 d . . . C20 C 0.7921(15) 0.0952(6) 0.0038(10) 0.038(4) Uani 1 1 d . . . H20 H 0.8629 0.0902 -0.0341 0.046 Uiso 1 1 calc R . . C21 C 0.6628(18) 0.0711(6) -0.0088(14) 0.057(6) Uani 1 1 d . . . H21 H 0.6443 0.0502 -0.0546 0.068 Uiso 1 1 calc R . . C22 C 0.5611(19) 0.0779(5) 0.0460(11) 0.043(5) Uani 1 1 d . . . H22 H 0.4714 0.0612 0.0387 0.052 Uiso 1 1 calc R . . C23 C 0.5885(15) 0.1086(6) 0.1115(10) 0.044(4) Uani 1 1 d . . . H23 H 0.5166 0.1129 0.1489 0.053 Uiso 1 1 calc R . . C24 C 0.7230(16) 0.1345(5) 0.1252(10) 0.036(4) Uani 1 1 d . . . C25 C 0.7407(16) 0.1648(5) 0.1955(9) 0.032(4) Uani 1 1 d . . . C26 C 0.701(2) 0.1882(6) 0.3240(11) 0.052(5) Uani 1 1 d . . . H26A H 0.7498 0.1674 0.3672 0.063 Uiso 1 1 calc R . . H26B H 0.6219 0.2064 0.3474 0.063 Uiso 1 1 calc R . . C27 C 0.8070(16) 0.2221(5) 0.2865(10) 0.037(4) Uani 1 1 d . . . H27 H 0.8971 0.2243 0.3246 0.045 Uiso 1 1 calc R . . C28 C 0.7474(16) 0.2739(5) 0.2694(10) 0.041(4) Uani 1 1 d . . . H28 H 0.8069 0.2882 0.2273 0.050 Uiso 1 1 calc R . . C29 C 0.773(2) 0.3066(6) 0.3479(12) 0.069(6) Uani 1 1 d . . . H29A H 0.7311 0.3387 0.3363 0.104 Uiso 1 1 calc R . . H29B H 0.8769 0.3098 0.3629 0.104 Uiso 1 1 calc R . . H29C H 0.7267 0.2918 0.3935 0.104 Uiso 1 1 calc R . . C30 C 0.5950(17) 0.2756(6) 0.2336(12) 0.059(5) Uani 1 1 d . . . H30A H 0.5790 0.2503 0.1918 0.088 Uiso 1 1 calc R . . H30B H 0.5752 0.3073 0.2082 0.088 Uiso 1 1 calc R . . H30C H 0.5301 0.2704 0.2771 0.088 Uiso 1 1 calc R . . Ir1A Ir 0.40545(6) 0.098492(19) 0.64654(4) 0.03213(16) Uani 1 1 d . . . O1A O 0.3430(11) 0.1664(4) 0.5889(7) 0.041(3) Uani 1 1 d . . . O2A O 0.0090(12) 0.0681(4) 0.5024(8) 0.052(3) Uani 1 1 d . . . N1A N 0.3222(13) 0.1166(4) 0.7469(9) 0.036(4) Uani 1 1 d . . . N2A N 0.4142(15) 0.1332(4) 0.8108(8) 0.040(3) Uani 1 1 d . . . N3A N 0.5070(12) 0.0764(4) 0.5540(9) 0.040(4) Uani 1 1 d . . . N4A N 0.5607(13) 0.0293(4) 0.5581(8) 0.031(3) Uani 1 1 d . . . N5A N 0.2098(13) 0.0708(5) 0.5859(8) 0.038(3) Uani 1 1 d . . . C1A C 0.1946(19) 0.1158(5) 0.7778(11) 0.045(5) Uani 1 1 d . . . H1A H 0.1072 0.1068 0.7470 0.053 Uiso 1 1 calc R . . C2A C 0.203(2) 0.1298(7) 0.8625(13) 0.060(5) Uani 1 1 d . . . H2A H 0.1276 0.1317 0.8983 0.072 Uiso 1 1 calc R . . C3A C 0.346(2) 0.1395(6) 0.8789(11) 0.060(6) Uani 1 1 d . . . H3A H 0.3907 0.1493 0.9307 0.072 Uiso 1 1 calc R . . C4A C 0.5574(19) 0.1409(5) 0.7877(10) 0.041(4) Uani 1 1 d . . . C5A C 0.663(2) 0.1613(5) 0.8450(12) 0.058(6) Uani 1 1 d . . . H5A H 0.6420 0.1681 0.8999 0.069 Uiso 1 1 calc R . . C6A C 0.795(2) 0.1707(6) 0.8188(13) 0.058(6) Uani 1 1 d . . . H6A H 0.8682 0.1846 0.8555 0.069 Uiso 1 1 calc R . . C7A C 0.824(2) 0.1601(6) 0.7373(16) 0.066(7) Uani 1 1 d . . . H7A H 0.9150 0.1673 0.7180 0.080 Uiso 1 1 calc R . . C8A C 0.7092(18) 0.1378(5) 0.6839(12) 0.049(5) Uani 1 1 d . . . H8A H 0.7284 0.1296 0.6294 0.059 Uiso 1 1 calc R . . C9A C 0.5799(15) 0.1285(5) 0.7077(9) 0.029(3) Uiso 1 1 d . . . C10A C 0.5440(16) 0.0907(6) 0.4798(10) 0.044(4) Uani 1 1 d . . . H10A H 0.5243 0.1222 0.4585 0.053 Uiso 1 1 calc R . . C11A C 0.6140(18) 0.0552(7) 0.4368(11) 0.053(5) Uani 1 1 d . . . H11A H 0.6471 0.0569 0.3834 0.063 Uiso 1 1 calc R . . C12A C 0.6228(16) 0.0169(6) 0.4913(10) 0.036(4) Uani 1 1 d . . . H12A H 0.6666 -0.0135 0.4822 0.044 Uiso 1 1 calc R . . C13A C 0.5442(17) 0.0075(6) 0.6331(11) 0.043(4) Uani 1 1 d . . . C14A C 0.5968(16) -0.0408(5) 0.6509(12) 0.046(5) Uani 1 1 d . . . H14A H 0.6412 -0.0593 0.6109 0.055 Uiso 1 1 calc R . . C15A C 0.5802(17) -0.0595(6) 0.7284(11) 0.043(4) Uani 1 1 d . . . H15A H 0.6159 -0.0910 0.7417 0.052 Uiso 1 1 calc R . . C16A C 0.5139(18) -0.0339(6) 0.7862(12) 0.048(5) Uani 1 1 d . . . H16A H 0.5040 -0.0473 0.8390 0.057 Uiso 1 1 calc R . . C17A C 0.4608(15) 0.0125(5) 0.7668(10) 0.035(4) Uani 1 1 d . . . H17A H 0.4123 0.0295 0.8068 0.042 Uiso 1 1 calc R . . C18A C 0.4751(16) 0.0341(5) 0.6943(9) 0.033(4) Uani 1 1 d . . . C19A C 0.2121(15) 0.1794(6) 0.5615(9) 0.030(4) Uani 1 1 d . . . C20A C 0.1811(19) 0.2300(6) 0.5503(12) 0.047(5) Uani 1 1 d . . . H20A H 0.2562 0.2527 0.5639 0.057 Uiso 1 1 calc R . . C21A C 0.052(2) 0.2466(8) 0.5218(11) 0.062(6) Uani 1 1 d . . . H21A H 0.0381 0.2804 0.5138 0.075 Uiso 1 1 calc R . . C22A C -0.064(2) 0.2144(9) 0.5032(11) 0.069(6) Uani 1 1 d . . . H22A H -0.1572 0.2266 0.4851 0.082 Uiso 1 1 calc R . . C23A C -0.0434(19) 0.1666(7) 0.5111(11) 0.055(5) Uani 1 1 d . . . H23A H -0.1211 0.1450 0.4969 0.065 Uiso 1 1 calc R . . C24A C 0.0947(17) 0.1477(6) 0.5405(10) 0.043(4) Uani 1 1 d . . . C25A C 0.1121(15) 0.0958(6) 0.5442(9) 0.037(4) Uani 1 1 d . . . C26A C 0.0634(18) 0.0189(6) 0.5066(11) 0.052(5) Uani 1 1 d . . . H26C H 0.1127 0.0106 0.4570 0.063 Uiso 1 1 calc R . . H26D H -0.0156 -0.0045 0.5125 0.063 Uiso 1 1 calc R . . C27A C 0.1689(16) 0.0196(5) 0.5826(11) 0.040(4) Uani 1 1 d . . . H27A H 0.2555 -0.0003 0.5720 0.048 Uiso 1 1 calc R . . C28A C 0.1117(16) 0.0030(6) 0.6626(11) 0.047(4) Uani 1 1 d . . . H28A H 0.1797 0.0161 0.7080 0.056 Uiso 1 1 calc R . . C29A C 0.120(2) -0.0527(6) 0.6696(14) 0.071(6) Uani 1 1 d . . . H29D H 0.0499 -0.0673 0.6288 0.106 Uiso 1 1 calc R . . H29E H 0.0988 -0.0626 0.7249 0.106 Uiso 1 1 calc R . . H29F H 0.2178 -0.0635 0.6595 0.106 Uiso 1 1 calc R . . C30A C -0.0373(18) 0.0227(7) 0.6769(13) 0.063(6) Uani 1 1 d . . . H30D H -0.0339 0.0581 0.6783 0.095 Uiso 1 1 calc R . . H30E H -0.0665 0.0105 0.7294 0.095 Uiso 1 1 calc R . . H30F H -0.1073 0.0121 0.6322 0.095 Uiso 1 1 calc R . . Ir1B Ir 0.30225(6) 0.400163(19) 0.76775(3) 0.02726(14) Uani 1 1 d . . . O1B O 0.3344(10) 0.3951(4) 0.6419(6) 0.036(2) Uani 1 1 d . . . O2B O 0.6723(11) 0.4874(4) 0.7353(7) 0.046(3) Uani 1 1 d . . . N1B N 0.4030(12) 0.3354(4) 0.7750(8) 0.032(3) Uani 1 1 d . . . N2B N 0.3090(13) 0.2967(4) 0.7538(8) 0.034(3) Uani 1 1 d . . . N3B N 0.1876(12) 0.4615(4) 0.7572(7) 0.029(3) Uani 1 1 d . . . N4B N 0.1425(11) 0.4792(4) 0.8288(8) 0.030(3) Uani 1 1 d . . . N5B N 0.4918(13) 0.4430(4) 0.7783(8) 0.031(3) Uani 1 1 d . . . C1B C 0.5338(14) 0.3178(6) 0.7816(9) 0.033(4) Uani 1 1 d . . . H1B H 0.6185 0.3358 0.7980 0.039 Uiso 1 1 calc R . . C2B C 0.5318(15) 0.2686(5) 0.7610(10) 0.036(4) Uani 1 1 d . . . H2B H 0.6127 0.2477 0.7589 0.043 Uiso 1 1 calc R . . C3B C 0.3895(15) 0.2568(5) 0.7445(9) 0.033(4) Uani 1 1 d . . . H3B H 0.3533 0.2257 0.7290 0.039 Uiso 1 1 calc R . . C4B C 0.1616(14) 0.3072(5) 0.7417(9) 0.028(3) Uani 1 1 d . . . C5B C 0.0566(15) 0.2719(5) 0.7233(9) 0.035(4) Uani 1 1 d . . . H5B H 0.0816 0.2386 0.7224 0.042 Uiso 1 1 calc R . . C6B C -0.0825(16) 0.2864(6) 0.7066(10) 0.040(4) Uani 1 1 d . . . H6B H -0.1553 0.2627 0.6947 0.049 Uiso 1 1 calc R . . C7B C -0.1209(17) 0.3344(6) 0.7065(11) 0.043(4) Uani 1 1 d . . . H7B H -0.2181 0.3441 0.6926 0.051 Uiso 1 1 calc R . . C8B C -0.0149(17) 0.3683(6) 0.7273(10) 0.044(4) Uani 1 1 d . . . H8B H -0.0418 0.4014 0.7284 0.053 Uiso 1 1 calc R . . C9B C 0.1262(14) 0.3566(5) 0.7462(9) 0.024(3) Uani 1 1 d . . . C10B C 0.1436(16) 0.4929(5) 0.6971(10) 0.033(4) Uani 1 1 d . . . H10B H 0.1623 0.4907 0.6409 0.040 Uiso 1 1 calc R . . C11B C 0.0675(17) 0.5285(5) 0.7317(11) 0.041(4) Uani 1 1 d . . . H11B H 0.0213 0.5548 0.7029 0.049 Uiso 1 1 calc R . . C12B C 0.0678(16) 0.5204(5) 0.8138(12) 0.046(5) Uani 1 1 d . . . H12B H 0.0242 0.5399 0.8527 0.056 Uiso 1 1 calc R . . C13B C 0.1782(15) 0.4508(6) 0.9000(10) 0.036(4) Uani 1 1 d . . . C14B C 0.1341(16) 0.4628(6) 0.9778(10) 0.038(4) Uani 1 1 d . . . H14B H 0.0772 0.4907 0.9854 0.045 Uiso 1 1 calc R . . C15B C 0.175(2) 0.4337(7) 1.0403(11) 0.053(5) Uani 1 1 d . . . H15B H 0.1469 0.4412 1.0935 0.064 Uiso 1 1 calc R . . C16B C 0.2552(18) 0.3937(7) 1.0300(10) 0.049(4) Uani 1 1 d . . . H16B H 0.2829 0.3735 1.0757 0.059 Uiso 1 1 calc R . . C17B C 0.2969(16) 0.3823(5) 0.9532(9) 0.035(4) Uani 1 1 d . . . H17B H 0.3533 0.3539 0.9484 0.042 Uiso 1 1 calc R . . C18B C 0.2628(15) 0.4090(5) 0.8828(9) 0.031(3) Uani 1 1 d . . . C19B C 0.4583(16) 0.4003(6) 0.6087(9) 0.036(4) Uani 1 1 d . . . C20B C 0.4696(19) 0.3765(6) 0.5340(10) 0.044(4) Uani 1 1 d . . . H20B H 0.3926 0.3570 0.5107 0.052 Uiso 1 1 calc R . . C21B C 0.593(2) 0.3818(7) 0.4951(13) 0.067(6) Uani 1 1 d . . . H21B H 0.6012 0.3659 0.4440 0.080 Uiso 1 1 calc R . . C22B C 0.704(2) 0.4092(10) 0.5279(14) 0.078(8) Uani 1 1 d . . . H22B H 0.7883 0.4118 0.4991 0.094 Uiso 1 1 calc R . . C23B C 0.7005(18) 0.4327(6) 0.5990(11) 0.047(5) Uani 1 1 d . . . H23B H 0.7784 0.4528 0.6194 0.056 Uiso 1 1 calc R . . C24B C 0.5781(17) 0.4268(5) 0.6424(10) 0.037(4) Uani 1 1 d . . . C25B C 0.5735(16) 0.4517(5) 0.7191(11) 0.036(4) Uani 1 1 d . . . C26B C 0.6365(16) 0.5086(6) 0.8108(10) 0.042(4) Uani 1 1 d . . . H26E H 0.5794 0.5385 0.8004 0.050 Uiso 1 1 calc R . . H26F H 0.7250 0.5164 0.8465 0.050 Uiso 1 1 calc R . . C27B C 0.5483(17) 0.4704(5) 0.8503(10) 0.040(4) Uani 1 1 d . . . H27B H 0.4664 0.4863 0.8758 0.047 Uiso 1 1 calc R . . C28B C 0.6324(16) 0.4394(6) 0.9137(11) 0.044(4) Uani 1 1 d . . . H28B H 0.5722 0.4101 0.9221 0.053 Uiso 1 1 calc R . . C29B C 0.6555(19) 0.4654(6) 0.9977(10) 0.055(5) Uani 1 1 d . . . H29G H 0.7082 0.4957 0.9913 0.083 Uiso 1 1 calc R . . H29H H 0.7113 0.4445 1.0371 0.083 Uiso 1 1 calc R . . H29I H 0.5614 0.4725 1.0181 0.083 Uiso 1 1 calc R . . C30B C 0.7773(16) 0.4216(5) 0.8889(11) 0.047(5) Uani 1 1 d . . . H30G H 0.7669 0.4112 0.8313 0.070 Uiso 1 1 calc R . . H30H H 0.8102 0.3943 0.9239 0.070 Uiso 1 1 calc R . . H30I H 0.8483 0.4478 0.8954 0.070 Uiso 1 1 calc R . . O3 O 0.0994(16) 0.4074(6) 0.5314(8) 0.092(5) Uani 1 1 d . . . O4 O 0.5343(12) 0.2181(4) 0.5087(7) 0.054(3) Uani 1 1 d . . . O5 O 0.1641(12) 0.0827(4) 0.0571(7) 0.058(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.0258(3) 0.0187(3) 0.0348(4) 0.0028(3) -0.0029(2) -0.0031(3) O1 0.043(7) 0.026(5) 0.024(6) 0.003(4) -0.005(5) -0.004(5) O2 0.043(7) 0.037(6) 0.052(8) 0.002(5) 0.014(6) -0.016(5) N1 0.026(7) 0.016(6) 0.040(8) -0.008(5) 0.002(6) -0.012(5) N2 0.039(7) 0.024(6) 0.030(8) 0.009(5) -0.011(6) 0.013(5) N3 0.041(8) 0.023(6) 0.027(7) -0.010(5) 0.009(6) -0.027(6) N4 0.035(7) 0.027(7) 0.026(7) 0.009(5) -0.005(5) 0.006(5) N5 0.037(7) 0.013(6) 0.042(8) 0.000(5) 0.005(6) 0.006(5) C1 0.031(9) 0.043(10) 0.050(11) 0.003(8) -0.010(8) 0.011(7) C2 0.052(12) 0.045(11) 0.065(14) 0.019(10) -0.008(10) 0.008(9) C3 0.056(11) 0.031(9) 0.047(11) 0.004(8) -0.010(9) 0.005(8) C4 0.034(9) 0.011(6) 0.036(9) 0.002(6) -0.012(7) 0.002(6) C5 0.061(12) 0.022(8) 0.028(9) 0.003(7) 0.012(8) -0.001(8) C6 0.044(10) 0.033(9) 0.030(9) -0.002(7) 0.006(7) -0.007(8) C7 0.028(8) 0.019(8) 0.038(9) -0.001(6) 0.007(7) 0.001(6) C8 0.055(10) 0.007(6) 0.051(10) 0.008(7) -0.016(8) -0.004(7) C9 0.033(8) 0.002(6) 0.044(9) -0.007(6) -0.012(7) 0.005(5) C10 0.043(10) 0.013(7) 0.063(13) 0.009(7) 0.011(9) 0.003(7) C11 0.040(10) 0.022(8) 0.053(12) 0.006(7) -0.010(8) 0.014(7) C12 0.041(10) 0.045(10) 0.026(9) 0.000(7) 0.001(7) -0.010(8) C13 0.041(10) 0.031(8) 0.024(8) 0.004(6) 0.005(7) 0.004(7) C14 0.065(12) 0.035(10) 0.031(10) 0.001(8) -0.003(8) -0.007(8) C15 0.051(11) 0.025(8) 0.066(13) -0.005(8) 0.001(9) -0.035(8) C16 0.040(10) 0.022(8) 0.056(12) -0.002(8) 0.002(8) -0.011(7) C17 0.021(8) 0.035(9) 0.049(11) 0.003(8) 0.004(7) -0.004(7) C18 0.030(9) 0.038(9) 0.022(8) 0.001(7) 0.001(6) 0.007(7) C19 0.033(9) 0.012(7) 0.048(11) 0.003(7) -0.009(8) -0.007(6) C20 0.032(9) 0.030(8) 0.050(10) 0.003(8) -0.013(7) 0.007(8) C21 0.039(11) 0.020(8) 0.106(18) -0.007(9) -0.028(11) -0.005(8) C22 0.042(11) 0.011(7) 0.074(14) -0.015(8) -0.008(9) -0.015(7) C23 0.027(8) 0.041(10) 0.059(11) 0.024(8) -0.024(8) -0.002(7) C24 0.028(9) 0.028(8) 0.050(11) 0.010(7) -0.012(8) -0.009(7) C25 0.037(9) 0.030(8) 0.029(9) 0.005(7) 0.010(7) 0.001(7) C26 0.061(12) 0.049(11) 0.049(12) 0.007(9) 0.015(10) -0.001(9) C27 0.027(8) 0.041(10) 0.045(10) -0.009(7) 0.011(7) -0.011(7) C28 0.032(9) 0.032(9) 0.061(12) -0.014(8) 0.011(8) 0.014(7) C29 0.119(18) 0.025(10) 0.064(14) -0.020(9) 0.006(13) -0.016(11) C30 0.043(11) 0.037(10) 0.097(16) -0.005(10) 0.011(10) 0.003(8) Ir1A 0.0294(3) 0.0222(3) 0.0434(4) 0.0005(3) -0.0051(3) 0.0016(3) O1A 0.043(7) 0.026(6) 0.053(8) 0.006(5) -0.011(6) 0.004(5) O2A 0.035(7) 0.052(8) 0.064(9) -0.009(6) -0.022(6) 0.003(6) N1A 0.020(7) 0.013(6) 0.070(11) 0.013(6) -0.026(7) -0.003(5) N2A 0.066(10) 0.018(6) 0.039(9) 0.009(6) 0.014(7) 0.008(6) N3A 0.015(6) 0.034(7) 0.066(10) 0.030(7) -0.019(6) -0.013(5) N4A 0.032(7) 0.023(7) 0.037(8) -0.003(6) -0.002(6) 0.010(5) N5A 0.026(7) 0.036(8) 0.049(9) 0.003(6) -0.014(6) 0.000(6) C1A 0.049(12) 0.026(9) 0.053(13) 0.011(8) -0.027(9) 0.007(8) C2A 0.073(15) 0.047(12) 0.059(15) 0.007(10) 0.003(11) -0.003(11) C3A 0.113(19) 0.035(10) 0.031(11) -0.001(8) 0.007(11) 0.010(11) C4A 0.070(12) 0.016(8) 0.034(10) 0.010(7) -0.010(9) 0.010(8) C5A 0.100(17) 0.011(8) 0.057(13) 0.014(8) -0.027(12) 0.009(9) C6A 0.079(16) 0.034(10) 0.052(14) 0.001(9) -0.045(12) -0.004(10) C7A 0.042(12) 0.017(9) 0.14(2) 0.029(11) -0.023(12) -0.002(8) C8A 0.058(12) 0.016(8) 0.069(14) 0.005(8) -0.018(10) 0.002(8) C10A 0.036(9) 0.041(10) 0.057(12) 0.009(9) 0.008(8) 0.008(8) C11A 0.046(11) 0.068(13) 0.043(12) -0.013(10) -0.012(9) 0.015(10) C12A 0.036(9) 0.034(9) 0.040(10) -0.015(8) 0.006(8) 0.005(7) C13A 0.040(10) 0.035(10) 0.054(12) 0.001(9) 0.000(8) 0.001(8) C14A 0.029(9) 0.018(8) 0.088(15) 0.003(8) -0.011(9) 0.006(7) C15A 0.041(10) 0.024(8) 0.064(13) 0.012(8) 0.006(9) -0.010(7) C16A 0.044(11) 0.029(9) 0.067(13) 0.012(9) -0.013(9) 0.015(8) C17A 0.029(8) 0.025(8) 0.051(11) -0.001(7) 0.003(7) 0.001(7) C18A 0.031(9) 0.036(9) 0.028(9) 0.001(7) -0.023(7) -0.015(7) C19A 0.022(8) 0.037(9) 0.028(9) 0.002(7) -0.007(7) 0.012(7) C20A 0.049(12) 0.021(8) 0.071(14) -0.005(8) -0.002(10) 0.007(8) C21A 0.082(16) 0.063(13) 0.041(12) 0.013(10) -0.004(11) 0.037(12) C22A 0.066(14) 0.084(17) 0.054(13) 0.017(13) -0.003(10) 0.032(14) C23A 0.050(12) 0.056(12) 0.056(13) 0.019(10) -0.009(9) 0.007(9) C24A 0.048(11) 0.033(9) 0.046(11) 0.006(8) -0.003(8) 0.017(8) C25A 0.029(8) 0.043(9) 0.037(9) 0.002(8) -0.013(7) -0.004(8) C26A 0.047(11) 0.040(10) 0.067(14) -0.001(9) -0.011(9) -0.004(8) C27A 0.026(9) 0.024(8) 0.066(13) 0.002(8) -0.013(8) -0.005(7) C28A 0.032(9) 0.037(10) 0.067(13) 0.002(9) -0.017(8) -0.015(8) C29A 0.062(14) 0.032(10) 0.12(2) -0.001(11) 0.002(12) -0.005(9) C30A 0.038(11) 0.049(12) 0.102(17) -0.001(11) -0.001(10) 0.002(9) Ir1B 0.0249(3) 0.0193(3) 0.0372(4) 0.0002(3) 0.0005(2) 0.0010(2) O1B 0.038(6) 0.025(5) 0.044(6) 0.002(5) -0.004(5) 0.001(5) O2B 0.031(6) 0.028(6) 0.078(9) 0.008(6) 0.006(6) -0.007(5) N1B 0.018(6) 0.024(6) 0.056(9) -0.006(6) 0.000(6) 0.003(5) N2B 0.036(8) 0.017(6) 0.047(9) 0.004(6) 0.001(6) -0.006(6) N3B 0.029(7) 0.035(7) 0.026(7) -0.004(6) 0.021(6) 0.001(5) N4B 0.016(6) 0.024(6) 0.049(9) 0.000(6) -0.004(6) 0.000(5) N5B 0.041(8) 0.017(6) 0.033(8) 0.000(5) 0.001(6) -0.002(6) C1B 0.014(7) 0.044(10) 0.038(10) 0.009(7) -0.004(6) 0.006(7) C2B 0.013(8) 0.024(8) 0.070(12) 0.003(8) 0.002(7) 0.003(6) C3B 0.035(9) 0.017(7) 0.048(10) -0.007(7) 0.018(7) 0.006(6) C4B 0.014(7) 0.029(8) 0.040(10) 0.005(7) -0.002(6) 0.004(6) C5B 0.028(9) 0.030(8) 0.046(11) 0.008(7) 0.003(7) -0.004(7) C6B 0.029(9) 0.039(10) 0.055(11) 0.000(8) 0.011(8) -0.017(8) C7B 0.027(9) 0.042(10) 0.061(12) 0.005(9) 0.017(8) 0.002(8) C8B 0.046(11) 0.030(9) 0.060(12) 0.011(8) 0.020(9) 0.015(8) C9B 0.019(8) 0.025(8) 0.030(9) 0.003(6) 0.008(6) -0.002(6) C10B 0.039(9) 0.024(8) 0.035(10) 0.002(7) -0.012(7) 0.000(7) C11B 0.044(10) 0.018(8) 0.060(13) 0.005(8) 0.004(9) 0.020(7) C12B 0.038(10) 0.025(9) 0.074(14) -0.018(9) -0.010(9) 0.000(7) C13B 0.016(8) 0.042(9) 0.050(11) -0.016(8) 0.005(7) -0.003(7) C14B 0.027(9) 0.031(9) 0.054(12) -0.009(8) 0.000(8) -0.005(7) C15B 0.069(13) 0.055(12) 0.038(11) -0.003(9) 0.021(9) -0.008(10) C16B 0.061(11) 0.051(11) 0.033(10) 0.018(9) -0.005(8) -0.013(10) C17B 0.047(10) 0.032(8) 0.027(9) -0.001(7) 0.004(7) -0.013(7) C18B 0.032(8) 0.016(8) 0.045(9) 0.012(7) 0.007(7) -0.009(6) C19B 0.043(10) 0.030(8) 0.035(9) 0.000(8) 0.000(7) 0.015(8) C20B 0.046(11) 0.058(12) 0.027(10) -0.010(8) 0.002(8) 0.017(9) C21B 0.079(16) 0.052(12) 0.071(15) 0.020(10) 0.013(13) 0.041(11) C22B 0.028(10) 0.13(2) 0.082(17) 0.021(16) 0.026(10) 0.036(13) C23B 0.044(11) 0.047(11) 0.053(12) 0.017(9) 0.017(9) 0.013(8) C24B 0.036(9) 0.028(9) 0.045(11) 0.023(8) 0.002(8) 0.018(7) C25B 0.030(9) 0.021(8) 0.056(12) 0.016(8) -0.004(8) -0.002(7) C26B 0.030(9) 0.029(9) 0.063(12) 0.009(8) -0.013(8) -0.019(7) C27B 0.038(10) 0.024(8) 0.054(11) -0.011(8) -0.012(8) -0.001(7) C28B 0.030(9) 0.040(10) 0.060(12) 0.006(9) -0.011(8) -0.007(8) C29B 0.064(13) 0.049(11) 0.049(12) 0.014(9) -0.024(9) -0.003(9) C30B 0.035(10) 0.019(8) 0.084(14) 0.008(8) -0.009(9) 0.010(7) O3 0.111(12) 0.088(12) 0.072(10) -0.017(9) -0.030(8) 0.049(10) O4 0.051(7) 0.048(8) 0.064(8) 0.012(6) 0.013(6) 0.013(6) O5 0.058(8) 0.055(8) 0.062(9) 0.009(6) 0.014(6) 0.024(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 N3 1.967(13) . ? Ir1 C9 1.998(15) . ? Ir1 N1 2.011(12) . ? Ir1 C18 2.016(15) . ? Ir1 N5 2.107(12) . ? Ir1 O1 2.156(10) . ? O1 C19 1.327(16) . ? O2 C25 1.336(16) . ? O2 C26 1.45(2) . ? N1 C1 1.333(18) . ? N1 N2 1.349(15) . ? N2 C3 1.375(18) . ? N2 C4 1.426(17) . ? N3 N4 1.328(15) . ? N3 C10 1.379(18) . ? N4 C12 1.362(18) . ? N4 C13 1.439(18) . ? N5 C25 1.313(18) . ? N5 C27 1.441(18) . ? C1 C2 1.40(2) . ? C1 H1 0.9500 . ? C2 C3 1.34(2) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C9 1.332(18) . ? C4 C5 1.388(19) . ? C5 C6 1.36(2) . ? C5 H5 0.9500 . ? C6 C7 1.359(19) . ? C6 H6 0.9500 . ? C7 C8 1.413(19) . ? C7 H7 0.9500 . ? C8 C9 1.394(19) . ? C8 H8 0.9500 . ? C10 C11 1.40(2) . ? C10 H10 0.9500 . ? C11 C12 1.36(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.362(19) . ? C13 C14 1.40(2) . ? C14 C15 1.44(2) . ? C14 H14 0.9500 . ? C15 C16 1.39(2) . ? C15 H15 0.9500 . ? C16 C17 1.37(2) . ? C16 H16 0.9500 . ? C17 C18 1.393(19) . ? C17 H17 0.9500 . ? C19 C24 1.36(2) . ? C19 C20 1.42(2) . ? C20 C21 1.37(2) . ? C20 H20 0.9500 . ? C21 C22 1.37(2) . ? C21 H21 0.9500 . ? C22 C23 1.37(2) . ? C22 H22 0.9500 . ? C23 C24 1.442(19) . ? C23 H23 0.9500 . ? C24 C25 1.42(2) . ? C26 C27 1.53(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.55(2) . ? C27 H27 1.0000 . ? C28 C30 1.49(2) . ? C28 C29 1.57(2) . ? C28 H28 1.0000 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? Ir1A N1A 1.936(15) . ? Ir1A N3A 1.945(15) . ? Ir1A C9A 2.009(15) . ? Ir1A C18A 2.028(15) . ? Ir1A N5A 2.135(12) . ? Ir1A O1A 2.157(10) . ? O1A C19A 1.309(17) . ? O2A C25A 1.363(17) . ? O2A C26A 1.451(19) . ? N1A C1A 1.33(2) . ? N1A N2A 1.369(17) . ? N2A C3A 1.34(2) . ? N2A C4A 1.43(2) . ? N3A C10A 1.346(19) . ? N3A N4A 1.396(16) . ? N4A C12A 1.322(18) . ? N4A C13A 1.38(2) . ? N5A C25A 1.287(18) . ? N5A C27A 1.467(18) . ? C1A C2A 1.43(2) . ? C1A H1A 0.9500 . ? C2A C3A 1.36(3) . ? C2A H2A 0.9500 . ? C3A H3A 0.9500 . ? C4A C9A 1.38(2) . ? C4A C5A 1.41(2) . ? C5A C6A 1.36(3) . ? C5A H5A 0.9500 . ? C6A C7A 1.41(3) . ? C6A H6A 0.9500 . ? C7A C8A 1.45(2) . ? C7A H7A 0.9500 . ? C8A C9A 1.32(2) . ? C8A H8A 0.9500 . ? C10A C11A 1.40(2) . ? C10A H10A 0.9500 . ? C11A C12A 1.38(2) . ? C11A H11A 0.9500 . ? C12A H12A 0.9500 . ? C13A C18A 1.43(2) . ? C13A C14A 1.44(2) . ? C14A C15A 1.39(2) . ? C14A H14A 0.9500 . ? C15A C16A 1.37(2) . ? C15A H15A 0.9500 . ? C16A C17A 1.40(2) . ? C16A H16A 0.9500 . ? C17A C18A 1.34(2) . ? C17A H17A 0.9500 . ? C19A C24A 1.42(2) . ? C19A C20A 1.44(2) . ? C20A C21A 1.33(2) . ? C20A H20A 0.9500 . ? C21A C22A 1.41(3) . ? C21A H21A 0.9500 . ? C22A C23A 1.34(3) . ? C22A H22A 0.9500 . ? C23A C24A 1.43(2) . ? C23A H23A 0.9500 . ? C24A C25A 1.45(2) . ? C26A C27A 1.51(2) . ? C26A H26C 0.9900 . ? C26A H26D 0.9900 . ? C27A C28A 1.52(2) . ? C27A H27A 1.0000 . ? C28A C30A 1.52(2) . ? C28A C29A 1.54(2) . ? C28A H28A 1.0000 . ? C29A H29D 0.9800 . ? C29A H29E 0.9800 . ? C29A H29F 0.9800 . ? C30A H30D 0.9800 . ? C30A H30E 0.9800 . ? C30A H30F 0.9800 . ? Ir1B C18B 1.959(15) . ? Ir1B N3B 2.002(12) . ? Ir1B N1B 2.020(11) . ? Ir1B C9B 2.038(13) . ? Ir1B O1B 2.105(10) . ? Ir1B N5B 2.116(12) . ? O1B C19B 1.321(16) . ? O2B C25B 1.359(17) . ? O2B C26B 1.429(19) . ? N1B C1B 1.304(16) . ? N1B N2B 1.405(16) . ? N2B C3B 1.348(17) . ? N2B C4B 1.398(17) . ? N3B C10B 1.347(18) . ? N3B N4B 1.367(15) . ? N4B C12B 1.345(18) . ? N4B C13B 1.418(19) . ? N5B C25B 1.301(19) . ? N5B C27B 1.458(18) . ? C1B C2B 1.40(2) . ? C1B H1B 0.9500 . ? C2B C3B 1.365(19) . ? C2B H2B 0.9500 . ? C3B H3B 0.9500 . ? C4B C5B 1.394(19) . ? C4B C9B 1.406(18) . ? C5B C6B 1.36(2) . ? C5B H5B 0.9500 . ? C6B C7B 1.37(2) . ? C6B H6B 0.9500 . ? C7B C8B 1.38(2) . ? C7B H7B 0.9500 . ? C8B C9B 1.36(2) . ? C8B H8B 0.9500 . ? C10B C11B 1.36(2) . ? C10B H10B 0.9500 . ? C11B C12B 1.36(2) . ? C11B H11B 0.9500 . ? C12B H12B 0.9500 . ? C13B C14B 1.41(2) . ? C13B C18B 1.44(2) . ? C14B C15B 1.33(2) . ? C14B H14B 0.9500 . ? C15B C16B 1.35(2) . ? C15B H15B 0.9500 . ? C16B C17B 1.38(2) . ? C16B H16B 0.9500 . ? C17B C18B 1.381(19) . ? C17B H17B 0.9500 . ? C19B C20B 1.40(2) . ? C19B C24B 1.40(2) . ? C20B C21B 1.37(2) . ? C20B H20B 0.9500 . ? C21B C22B 1.35(3) . ? C21B H21B 0.9500 . ? C22B C23B 1.33(3) . ? C22B H22B 0.9500 . ? C23B C24B 1.40(2) . ? C23B H23B 0.9500 . ? C24B C25B 1.43(2) . ? C26B C27B 1.51(2) . ? C26B H26E 0.9900 . ? C26B H26F 0.9900 . ? C27B C28B 1.51(2) . ? C27B H27B 1.0000 . ? C28B C30B 1.52(2) . ? C28B C29B 1.55(2) . ? C28B H28B 1.0000 . ? C29B H29G 0.9800 . ? C29B H29H 0.9800 . ? C29B H29I 0.9800 . ? C30B H30G 0.9800 . ? C30B H30H 0.9800 . ? C30B H30I 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Ir1 C9 95.8(5) . . ? N3 Ir1 N1 173.7(4) . . ? C9 Ir1 N1 79.0(5) . . ? N3 Ir1 C18 78.1(5) . . ? C9 Ir1 C18 88.4(5) . . ? N1 Ir1 C18 98.0(5) . . ? N3 Ir1 N5 87.9(5) . . ? C9 Ir1 N5 175.4(5) . . ? N1 Ir1 N5 97.5(5) . . ? C18 Ir1 N5 95.0(5) . . ? N3 Ir1 O1 96.0(4) . . ? C9 Ir1 O1 90.5(4) . . ? N1 Ir1 O1 87.7(4) . . ? C18 Ir1 O1 173.9(5) . . ? N5 Ir1 O1 86.4(4) . . ? C19 O1 Ir1 125.7(9) . . ? C25 O2 C26 108.2(12) . . ? C1 N1 N2 105.9(13) . . ? C1 N1 Ir1 138.7(11) . . ? N2 N1 Ir1 115.4(9) . . ? N1 N2 C3 109.6(13) . . ? N1 N2 C4 114.2(11) . . ? C3 N2 C4 136.0(14) . . ? N4 N3 C10 104.1(13) . . ? N4 N3 Ir1 119.0(9) . . ? C10 N3 Ir1 136.9(11) . . ? N3 N4 C12 115.1(12) . . ? N3 N4 C13 113.5(11) . . ? C12 N4 C13 131.4(13) . . ? C25 N5 C27 107.5(12) . . ? C25 N5 Ir1 125.9(10) . . ? C27 N5 Ir1 126.4(9) . . ? N1 C1 C2 110.7(15) . . ? N1 C1 H1 124.6 . . ? C2 C1 H1 124.6 . . ? C3 C2 C1 105.4(15) . . ? C3 C2 H2 127.3 . . ? C1 C2 H2 127.3 . . ? C2 C3 N2 108.4(15) . . ? C2 C3 H3 125.8 . . ? N2 C3 H3 125.8 . . ? C9 C4 C5 124.7(14) . . ? C9 C4 N2 115.3(13) . . ? C5 C4 N2 119.9(13) . . ? C6 C5 C4 120.0(15) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 116.8(14) . . ? C7 C6 H6 121.6 . . ? C5 C6 H6 121.6 . . ? C6 C7 C8 123.1(14) . . ? C6 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C9 C8 C7 118.8(13) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C4 C9 C8 116.4(14) . . ? C4 C9 Ir1 116.0(10) . . ? C8 C9 Ir1 127.4(11) . . ? N3 C10 C11 108.0(14) . . ? N3 C10 H10 126.0 . . ? C11 C10 H10 126.0 . . ? C12 C11 C10 108.9(14) . . ? C12 C11 H11 125.5 . . ? C10 C11 H11 125.5 . . ? C11 C12 N4 103.7(13) . . ? C11 C12 H12 128.1 . . ? N4 C12 H12 128.1 . . ? C18 C13 C14 126.1(15) . . ? C18 C13 N4 113.4(13) . . ? C14 C13 N4 120.4(13) . . ? C13 C14 C15 114.5(15) . . ? C13 C14 H14 122.8 . . ? C15 C14 H14 122.8 . . ? C16 C15 C14 121.0(15) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C17 C16 C15 118.9(15) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C16 C17 C18 123.4(16) . . ? C16 C17 H17 118.3 . . ? C18 C17 H17 118.3 . . ? C13 C18 C17 115.9(14) . . ? C13 C18 Ir1 115.8(11) . . ? C17 C18 Ir1 128.3(12) . . ? O1 C19 C24 125.6(14) . . ? O1 C19 C20 115.7(14) . . ? C24 C19 C20 118.6(14) . . ? C21 C20 C19 122.9(16) . . ? C21 C20 H20 118.5 . . ? C19 C20 H20 118.5 . . ? C22 C21 C20 118.7(17) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 120.1(15) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 122.0(16) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C19 C24 C25 125.0(14) . . ? C19 C24 C23 117.6(15) . . ? C25 C24 C23 117.3(15) . . ? N5 C25 O2 114.1(13) . . ? N5 C25 C24 127.7(14) . . ? O2 C25 C24 118.2(14) . . ? O2 C26 C27 101.3(13) . . ? O2 C26 H26A 111.5 . . ? C27 C26 H26A 111.5 . . ? O2 C26 H26B 111.5 . . ? C27 C26 H26B 111.5 . . ? H26A C26 H26B 109.3 . . ? N5 C27 C26 104.1(12) . . ? N5 C27 C28 112.0(13) . . ? C26 C27 C28 113.9(13) . . ? N5 C27 H27 108.9 . . ? C26 C27 H27 108.9 . . ? C28 C27 H27 108.9 . . ? C30 C28 C27 114.5(13) . . ? C30 C28 C29 112.0(14) . . ? C27 C28 C29 111.0(14) . . ? C30 C28 H28 106.2 . . ? C27 C28 H28 106.2 . . ? C29 C28 H28 106.2 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N1A Ir1A N3A 173.2(5) . . ? N1A Ir1A C9A 80.5(5) . . ? N3A Ir1A C9A 95.3(5) . . ? N1A Ir1A C18A 92.3(6) . . ? N3A Ir1A C18A 82.2(6) . . ? C9A Ir1A C18A 87.4(6) . . ? N1A Ir1A N5A 95.7(5) . . ? N3A Ir1A N5A 88.7(5) . . ? C9A Ir1A N5A 175.4(5) . . ? C18A Ir1A N5A 95.4(5) . . ? N1A Ir1A O1A 91.8(4) . . ? N3A Ir1A O1A 93.7(5) . . ? C9A Ir1A O1A 91.9(5) . . ? C18A Ir1A O1A 175.7(6) . . ? N5A Ir1A O1A 85.6(4) . . ? C19A O1A Ir1A 126.6(10) . . ? C25A O2A C26A 106.0(12) . . ? C1A N1A N2A 103.7(14) . . ? C1A N1A Ir1A 138.6(11) . . ? N2A N1A Ir1A 117.6(10) . . ? C3A N2A N1A 111.6(15) . . ? C3A N2A C4A 135.8(17) . . ? N1A N2A C4A 112.6(13) . . ? C10A N3A N4A 101.5(13) . . ? C10A N3A Ir1A 141.7(11) . . ? N4A N3A Ir1A 116.8(9) . . ? C12A N4A C13A 134.9(14) . . ? C12A N4A N3A 112.4(13) . . ? C13A N4A N3A 112.5(12) . . ? C25A N5A C27A 109.2(12) . . ? C25A N5A Ir1A 125.9(11) . . ? C27A N5A Ir1A 124.8(9) . . ? N1A C1A C2A 112.7(16) . . ? N1A C1A H1A 123.7 . . ? C2A C1A H1A 123.7 . . ? C3A C2A C1A 102.4(18) . . ? C3A C2A H2A 128.8 . . ? C1A C2A H2A 128.8 . . ? N2A C3A C2A 109.6(18) . . ? N2A C3A H3A 125.2 . . ? C2A C3A H3A 125.2 . . ? C9A C4A C5A 125.0(18) . . ? C9A C4A N2A 115.5(14) . . ? C5A C4A N2A 119.5(17) . . ? C6A C5A C4A 117.4(19) . . ? C6A C5A H5A 121.3 . . ? C4A C5A H5A 121.3 . . ? C5A C6A C7A 120.5(17) . . ? C5A C6A H6A 119.8 . . ? C7A C6A H6A 119.8 . . ? C6A C7A C8A 117.7(19) . . ? C6A C7A H7A 121.1 . . ? C8A C7A H7A 121.1 . . ? C9A C8A C7A 122.9(19) . . ? C9A C8A H8A 118.5 . . ? C7A C8A H8A 118.5 . . ? C8A C9A C4A 116.4(15) . . ? C8A C9A Ir1A 130.5(13) . . ? C4A C9A Ir1A 113.1(11) . . ? N3A C10A C11A 114.3(16) . . ? N3A C10A H10A 122.8 . . ? C11A C10A H10A 122.8 . . ? C12A C11A C10A 102.6(16) . . ? C12A C11A H11A 128.7 . . ? C10A C11A H11A 128.7 . . ? N4A C12A C11A 109.2(14) . . ? N4A C12A H12A 125.4 . . ? C11A C12A H12A 125.4 . . ? N4A C13A C18A 118.9(14) . . ? N4A C13A C14A 121.3(16) . . ? C18A C13A C14A 119.8(16) . . ? C15A C14A C13A 117.8(16) . . ? C15A C14A H14A 121.1 . . ? C13A C14A H14A 121.1 . . ? C16A C15A C14A 121.9(16) . . ? C16A C15A H15A 119.0 . . ? C14A C15A H15A 119.0 . . ? C15A C16A C17A 119.2(17) . . ? C15A C16A H16A 120.4 . . ? C17A C16A H16A 120.4 . . ? C18A C17A C16A 123.3(16) . . ? C18A C17A H17A 118.4 . . ? C16A C17A H17A 118.4 . . ? C17A C18A C13A 118.0(15) . . ? C17A C18A Ir1A 132.7(13) . . ? C13A C18A Ir1A 109.2(11) . . ? O1A C19A C24A 125.8(14) . . ? O1A C19A C20A 118.8(15) . . ? C24A C19A C20A 115.4(13) . . ? C21A C20A C19A 123.1(18) . . ? C21A C20A H20A 118.5 . . ? C19A C20A H20A 118.5 . . ? C20A C21A C22A 120.5(19) . . ? C20A C21A H21A 119.7 . . ? C22A C21A H21A 119.7 . . ? C23A C22A C21A 119.9(18) . . ? C23A C22A H22A 120.1 . . ? C21A C22A H22A 120.1 . . ? C22A C23A C24A 120.7(18) . . ? C22A C23A H23A 119.7 . . ? C24A C23A H23A 119.7 . . ? C19A C24A C23A 120.4(15) . . ? C19A C24A C25A 121.5(14) . . ? C23A C24A C25A 118.1(16) . . ? N5A C25A O2A 113.4(15) . . ? N5A C25A C24A 128.8(14) . . ? O2A C25A C24A 117.7(13) . . ? O2A C26A C27A 103.0(13) . . ? O2A C26A H26C 111.2 . . ? C27A C26A H26C 111.2 . . ? O2A C26A H26D 111.2 . . ? C27A C26A H26D 111.2 . . ? H26C C26A H26D 109.1 . . ? N5A C27A C26A 100.9(13) . . ? N5A C27A C28A 111.6(14) . . ? C26A C27A C28A 116.8(13) . . ? N5A C27A H27A 109.0 . . ? C26A C27A H27A 109.0 . . ? C28A C27A H27A 109.0 . . ? C30A C28A C27A 114.3(14) . . ? C30A C28A C29A 112.8(14) . . ? C27A C28A C29A 110.1(15) . . ? C30A C28A H28A 106.4 . . ? C27A C28A H28A 106.4 . . ? C29A C28A H28A 106.4 . . ? C28A C29A H29D 109.5 . . ? C28A C29A H29E 109.5 . . ? H29D C29A H29E 109.5 . . ? C28A C29A H29F 109.5 . . ? H29D C29A H29F 109.5 . . ? H29E C29A H29F 109.5 . . ? C28A C30A H30D 109.5 . . ? C28A C30A H30E 109.5 . . ? H30D C30A H30E 109.5 . . ? C28A C30A H30F 109.5 . . ? H30D C30A H30F 109.5 . . ? H30E C30A H30F 109.5 . . ? C18B Ir1B N3B 80.5(5) . . ? C18B Ir1B N1B 100.2(5) . . ? N3B Ir1B N1B 175.3(5) . . ? C18B Ir1B C9B 91.5(5) . . ? N3B Ir1B C9B 94.2(5) . . ? N1B Ir1B C9B 81.2(5) . . ? C18B Ir1B O1B 175.7(5) . . ? N3B Ir1B O1B 95.2(4) . . ? N1B Ir1B O1B 84.0(5) . . ? C9B Ir1B O1B 88.3(5) . . ? C18B Ir1B N5B 94.2(5) . . ? N3B Ir1B N5B 88.0(5) . . ? N1B Ir1B N5B 96.5(5) . . ? C9B Ir1B N5B 174.1(5) . . ? O1B Ir1B N5B 86.0(4) . . ? C19B O1B Ir1B 126.5(9) . . ? C25B O2B C26B 105.2(12) . . ? C1B N1B N2B 107.0(12) . . ? C1B N1B Ir1B 139.3(10) . . ? N2B N1B Ir1B 112.7(8) . . ? C3B N2B C4B 134.5(12) . . ? C3B N2B N1B 108.2(11) . . ? C4B N2B N1B 117.1(11) . . ? C10B N3B N4B 107.2(12) . . ? C10B N3B Ir1B 137.3(10) . . ? N4B N3B Ir1B 115.4(9) . . ? C12B N4B N3B 109.7(13) . . ? C12B N4B C13B 134.4(14) . . ? N3B N4B C13B 115.8(11) . . ? C25B N5B C27B 108.0(13) . . ? C25B N5B Ir1B 125.2(11) . . ? C27B N5B Ir1B 126.7(10) . . ? N1B C1B C2B 110.4(13) . . ? N1B C1B H1B 124.8 . . ? C2B C1B H1B 124.8 . . ? C3B C2B C1B 105.8(12) . . ? C3B C2B H2B 127.1 . . ? C1B C2B H2B 127.1 . . ? N2B C3B C2B 108.6(13) . . ? N2B C3B H3B 125.7 . . ? C2B C3B H3B 125.7 . . ? C5B C4B N2B 122.9(13) . . ? C5B C4B C9B 121.9(12) . . ? N2B C4B C9B 115.2(12) . . ? C6B C5B C4B 118.2(14) . . ? C6B C5B H5B 120.9 . . ? C4B C5B H5B 120.9 . . ? C5B C6B C7B 121.9(15) . . ? C5B C6B H6B 119.1 . . ? C7B C6B H6B 119.1 . . ? C6B C7B C8B 118.4(15) . . ? C6B C7B H7B 120.8 . . ? C8B C7B H7B 120.8 . . ? C9B C8B C7B 123.3(15) . . ? C9B C8B H8B 118.4 . . ? C7B C8B H8B 118.4 . . ? C8B C9B C4B 116.3(13) . . ? C8B C9B Ir1B 130.0(11) . . ? C4B C9B Ir1B 113.3(10) . . ? N3B C10B C11B 107.4(15) . . ? N3B C10B H10B 126.3 . . ? C11B C10B H10B 126.3 . . ? C12B C11B C10B 109.5(15) . . ? C12B C11B H11B 125.2 . . ? C10B C11B H11B 125.2 . . ? N4B C12B C11B 106.1(14) . . ? N4B C12B H12B 127.0 . . ? C11B C12B H12B 127.0 . . ? C14B C13B N4B 123.0(14) . . ? C14B C13B C18B 124.8(15) . . ? N4B C13B C18B 112.2(13) . . ? C15B C14B C13B 117.8(15) . . ? C15B C14B H14B 121.1 . . ? C13B C14B H14B 121.1 . . ? C14B C15B C16B 121.6(16) . . ? C14B C15B H15B 119.2 . . ? C16B C15B H15B 119.2 . . ? C15B C16B C17B 120.0(16) . . ? C15B C16B H16B 120.0 . . ? C17B C16B H16B 120.0 . . ? C18B C17B C16B 124.9(15) . . ? C18B C17B H17B 117.6 . . ? C16B C17B H17B 117.6 . . ? C17B C18B C13B 111.0(14) . . ? C17B C18B Ir1B 133.1(11) . . ? C13B C18B Ir1B 116.0(11) . . ? O1B C19B C20B 116.1(15) . . ? O1B C19B C24B 125.7(14) . . ? C20B C19B C24B 118.2(15) . . ? C21B C20B C19B 119.0(18) . . ? C21B C20B H20B 120.5 . . ? C19B C20B H20B 120.5 . . ? C22B C21B C20B 121(2) . . ? C22B C21B H21B 119.5 . . ? C20B C21B H21B 119.5 . . ? C23B C22B C21B 123.0(19) . . ? C23B C22B H22B 118.5 . . ? C21B C22B H22B 118.5 . . ? C22B C23B C24B 117.7(19) . . ? C22B C23B H23B 121.1 . . ? C24B C23B H23B 121.1 . . ? C23B C24B C19B 120.8(16) . . ? C23B C24B C25B 118.2(16) . . ? C19B C24B C25B 120.8(14) . . ? N5B C25B O2B 114.6(15) . . ? N5B C25B C24B 128.6(14) . . ? O2B C25B C24B 116.7(14) . . ? O2B C26B C27B 104.9(12) . . ? O2B C26B H26E 110.8 . . ? C27B C26B H26E 110.8 . . ? O2B C26B H26F 110.8 . . ? C27B C26B H26F 110.8 . . ? H26E C26B H26F 108.9 . . ? N5B C27B C28B 112.8(12) . . ? N5B C27B C26B 101.0(13) . . ? C28B C27B C26B 114.9(13) . . ? N5B C27B H27B 109.3 . . ? C28B C27B H27B 109.3 . . ? C26B C27B H27B 109.3 . . ? C27B C28B C30B 114.8(15) . . ? C27B C28B C29B 111.7(13) . . ? C30B C28B C29B 109.1(13) . . ? C27B C28B H28B 106.9 . . ? C30B C28B H28B 106.9 . . ? C29B C28B H28B 106.9 . . ? C28B C29B H29G 109.5 . . ? C28B C29B H29H 109.5 . . ? H29G C29B H29H 109.5 . . ? C28B C29B H29I 109.5 . . ? H29G C29B H29I 109.5 . . ? H29H C29B H29I 109.5 . . ? C28B C30B H30G 109.5 . . ? C28B C30B H30H 109.5 . . ? H30G C30B H30H 109.5 . . ? C28B C30B H30I 109.5 . . ? H30G C30B H30I 109.5 . . ? H30H C30B H30I 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 N3 Ir1 O1 C19 105.8(11) . . . . ? C9 Ir1 O1 C19 -158.4(11) . . . . ? N1 Ir1 O1 C19 -79.4(11) . . . . ? N5 Ir1 O1 C19 18.3(11) . . . . ? C9 Ir1 N1 C1 -177.2(15) . . . . ? C18 Ir1 N1 C1 -90.4(15) . . . . ? N5 Ir1 N1 C1 5.7(15) . . . . ? O1 Ir1 N1 C1 91.8(15) . . . . ? C9 Ir1 N1 N2 1.2(9) . . . . ? C18 Ir1 N1 N2 88.1(9) . . . . ? N5 Ir1 N1 N2 -175.8(9) . . . . ? O1 Ir1 N1 N2 -89.7(9) . . . . ? C1 N1 N2 C3 0.0(15) . . . . ? Ir1 N1 N2 C3 -179.0(9) . . . . ? C1 N1 N2 C4 175.9(12) . . . . ? Ir1 N1 N2 C4 -3.1(14) . . . . ? C9 Ir1 N3 N4 89.2(10) . . . . ? C18 Ir1 N3 N4 2.0(9) . . . . ? N5 Ir1 N3 N4 -93.5(10) . . . . ? O1 Ir1 N3 N4 -179.6(9) . . . . ? C9 Ir1 N3 C10 -86.5(14) . . . . ? C18 Ir1 N3 C10 -173.6(15) . . . . ? N5 Ir1 N3 C10 90.8(14) . . . . ? O1 Ir1 N3 C10 4.7(14) . . . . ? C10 N3 N4 C12 -2.8(15) . . . . ? Ir1 N3 N4 C12 -179.7(9) . . . . ? C10 N3 N4 C13 176.9(11) . . . . ? Ir1 N3 N4 C13 0.0(14) . . . . ? N3 Ir1 N5 C25 -101.4(12) . . . . ? N1 Ir1 N5 C25 82.0(12) . . . . ? C18 Ir1 N5 C25 -179.3(12) . . . . ? O1 Ir1 N5 C25 -5.2(12) . . . . ? N3 Ir1 N5 C27 74.2(12) . . . . ? N1 Ir1 N5 C27 -102.4(12) . . . . ? C18 Ir1 N5 C27 -3.7(12) . . . . ? O1 Ir1 N5 C27 170.4(12) . . . . ? N2 N1 C1 C2 -0.4(17) . . . . ? Ir1 N1 C1 C2 178.1(12) . . . . ? N1 C1 C2 C3 1(2) . . . . ? C1 C2 C3 N2 -0.7(19) . . . . ? N1 N2 C3 C2 0.5(18) . . . . ? C4 N2 C3 C2 -174.1(16) . . . . ? N1 N2 C4 C9 3.9(17) . . . . ? C3 N2 C4 C9 178.3(15) . . . . ? N1 N2 C4 C5 -178.3(12) . . . . ? C3 N2 C4 C5 -4(2) . . . . ? C9 C4 C5 C6 -4(2) . . . . ? N2 C4 C5 C6 178.6(13) . . . . ? C4 C5 C6 C7 1(2) . . . . ? C5 C6 C7 C8 1(2) . . . . ? C6 C7 C8 C9 -1(2) . . . . ? C5 C4 C9 C8 4(2) . . . . ? N2 C4 C9 C8 -178.0(12) . . . . ? C5 C4 C9 Ir1 179.4(11) . . . . ? N2 C4 C9 Ir1 -2.9(15) . . . . ? C7 C8 C9 C4 -2.1(19) . . . . ? C7 C8 C9 Ir1 -176.5(10) . . . . ? N3 Ir1 C9 C4 -175.4(10) . . . . ? N1 Ir1 C9 C4 1.0(10) . . . . ? C18 Ir1 C9 C4 -97.5(11) . . . . ? O1 Ir1 C9 C4 88.5(10) . . . . ? N3 Ir1 C9 C8 -1.0(12) . . . . ? N1 Ir1 C9 C8 175.4(12) . . . . ? C18 Ir1 C9 C8 76.9(12) . . . . ? O1 Ir1 C9 C8 -97.1(11) . . . . ? N4 N3 C10 C11 3.2(15) . . . . ? Ir1 N3 C10 C11 179.3(11) . . . . ? N3 C10 C11 C12 -2.8(18) . . . . ? C10 C11 C12 N4 1.1(17) . . . . ? N3 N4 C12 C11 1.1(17) . . . . ? C13 N4 C12 C11 -178.5(14) . . . . ? N3 N4 C13 C18 -3.2(17) . . . . ? C12 N4 C13 C18 176.5(14) . . . . ? N3 N4 C13 C14 -179.2(12) . . . . ? C12 N4 C13 C14 0(2) . . . . ? C18 C13 C14 C15 3(2) . . . . ? N4 C13 C14 C15 178.3(13) . . . . ? C13 C14 C15 C16 -4(2) . . . . ? C14 C15 C16 C17 2(2) . . . . ? C15 C16 C17 C18 1(2) . . . . ? C14 C13 C18 C17 1(2) . . . . ? N4 C13 C18 C17 -175.2(12) . . . . ? C14 C13 C18 Ir1 -179.4(12) . . . . ? N4 C13 C18 Ir1 4.9(16) . . . . ? C16 C17 C18 C13 -3(2) . . . . ? C16 C17 C18 Ir1 177.1(11) . . . . ? N3 Ir1 C18 C13 -3.8(10) . . . . ? C9 Ir1 C18 C13 -100.0(11) . . . . ? N1 Ir1 C18 C13 -178.7(11) . . . . ? N5 Ir1 C18 C13 83.0(11) . . . . ? N3 Ir1 C18 C17 176.3(14) . . . . ? C9 Ir1 C18 C17 80.1(13) . . . . ? N1 Ir1 C18 C17 1.4(14) . . . . ? N5 Ir1 C18 C17 -96.9(13) . . . . ? Ir1 O1 C19 C24 -19(2) . . . . ? Ir1 O1 C19 C20 162.4(10) . . . . ? O1 C19 C20 C21 178.4(14) . . . . ? C24 C19 C20 C21 0(2) . . . . ? C19 C20 C21 C22 -1(2) . . . . ? C20 C21 C22 C23 1(3) . . . . ? C21 C22 C23 C24 0(2) . . . . ? O1 C19 C24 C25 1(2) . . . . ? C20 C19 C24 C25 179.1(14) . . . . ? O1 C19 C24 C23 -177.7(13) . . . . ? C20 C19 C24 C23 1(2) . . . . ? C22 C23 C24 C19 -1(2) . . . . ? C22 C23 C24 C25 -179.1(14) . . . . ? C27 N5 C25 O2 -5.0(17) . . . . ? Ir1 N5 C25 O2 171.3(9) . . . . ? C27 N5 C25 C24 175.0(15) . . . . ? Ir1 N5 C25 C24 -9(2) . . . . ? C26 O2 C25 N5 -9.7(18) . . . . ? C26 O2 C25 C24 170.2(13) . . . . ? C19 C24 C25 N5 15(3) . . . . ? C23 C24 C25 N5 -166.7(14) . . . . ? C19 C24 C25 O2 -165.0(14) . . . . ? C23 C24 C25 O2 13(2) . . . . ? C25 O2 C26 C27 18.8(16) . . . . ? C25 N5 C27 C26 16.6(16) . . . . ? Ir1 N5 C27 C26 -159.6(10) . . . . ? C25 N5 C27 C28 -107.0(14) . . . . ? Ir1 N5 C27 C28 76.8(15) . . . . ? O2 C26 C27 N5 -21.0(16) . . . . ? O2 C26 C27 C28 101.3(15) . . . . ? N5 C27 C28 C30 75.8(17) . . . . ? C26 C27 C28 C30 -42(2) . . . . ? N5 C27 C28 C29 -156.1(13) . . . . ? C26 C27 C28 C29 85.9(17) . . . . ? N1A Ir1A O1A C19A -73.5(12) . . . . ? N3A Ir1A O1A C19A 110.5(12) . . . . ? C9A Ir1A O1A C19A -154.1(12) . . . . ? N5A Ir1A O1A C19A 22.1(12) . . . . ? C9A Ir1A N1A C1A 176.6(15) . . . . ? C18A Ir1A N1A C1A -96.5(15) . . . . ? N5A Ir1A N1A C1A -0.8(15) . . . . ? O1A Ir1A N1A C1A 85.0(15) . . . . ? C9A Ir1A N1A N2A -8.4(9) . . . . ? C18A Ir1A N1A N2A 78.5(9) . . . . ? N5A Ir1A N1A N2A 174.3(9) . . . . ? O1A Ir1A N1A N2A -100.0(9) . . . . ? C1A N1A N2A C3A 3.3(15) . . . . ? Ir1A N1A N2A C3A -173.3(10) . . . . ? C1A N1A N2A C4A -174.8(11) . . . . ? Ir1A N1A N2A C4A 8.6(13) . . . . ? C9A Ir1A N3A C10A -89.8(17) . . . . ? C18A Ir1A N3A C10A -176.4(17) . . . . ? N5A Ir1A N3A C10A 87.9(17) . . . . ? O1A Ir1A N3A C10A 2.5(17) . . . . ? C9A Ir1A N3A N4A 93.3(10) . . . . ? C18A Ir1A N3A N4A 6.7(9) . . . . ? N5A Ir1A N3A N4A -89.0(10) . . . . ? O1A Ir1A N3A N4A -174.5(9) . . . . ? C10A N3A N4A C12A -0.5(16) . . . . ? Ir1A N3A N4A C12A 177.5(10) . . . . ? C10A N3A N4A C13A 175.8(13) . . . . ? Ir1A N3A N4A C13A -6.2(15) . . . . ? N1A Ir1A N5A C25A 85.4(14) . . . . ? N3A Ir1A N5A C25A -99.8(14) . . . . ? C18A Ir1A N5A C25A 178.2(14) . . . . ? O1A Ir1A N5A C25A -6.0(14) . . . . ? N1A Ir1A N5A C27A -97.3(13) . . . . ? N3A Ir1A N5A C27A 77.5(13) . . . . ? C18A Ir1A N5A C27A -4.5(14) . . . . ? O1A Ir1A N5A C27A 171.3(13) . . . . ? N2A N1A C1A C2A -2.4(16) . . . . ? Ir1A N1A C1A C2A 173.1(12) . . . . ? N1A C1A C2A C3A 0.7(19) . . . . ? N1A N2A C3A C2A -3.1(19) . . . . ? C4A N2A C3A C2A 174.4(15) . . . . ? C1A C2A C3A N2A 1.4(19) . . . . ? C3A N2A C4A C9A 179.7(16) . . . . ? N1A N2A C4A C9A -2.9(16) . . . . ? C3A N2A C4A C5A -2(2) . . . . ? N1A N2A C4A C5A 175.5(12) . . . . ? C9A C4A C5A C6A 2(2) . . . . ? N2A C4A C5A C6A -176.0(14) . . . . ? C4A C5A C6A C7A 0(2) . . . . ? C5A C6A C7A C8A -1(2) . . . . ? C6A C7A C8A C9A 2(2) . . . . ? C7A C8A C9A C4A 0(2) . . . . ? C7A C8A C9A Ir1A 179.9(11) . . . . ? C5A C4A C9A C8A -2(2) . . . . ? N2A C4A C9A C8A 176.5(13) . . . . ? C5A C4A C9A Ir1A 178.1(11) . . . . ? N2A C4A C9A Ir1A -3.7(16) . . . . ? N1A Ir1A C9A C8A -173.8(15) . . . . ? N3A Ir1A C9A C8A 11.6(15) . . . . ? C18A Ir1A C9A C8A 93.4(15) . . . . ? O1A Ir1A C9A C8A -82.3(15) . . . . ? N1A Ir1A C9A C4A 6.4(10) . . . . ? N3A Ir1A C9A C4A -168.2(10) . . . . ? C18A Ir1A C9A C4A -86.3(11) . . . . ? O1A Ir1A C9A C4A 97.9(11) . . . . ? N4A N3A C10A C11A 1.4(18) . . . . ? Ir1A N3A C10A C11A -175.8(12) . . . . ? N3A C10A C11A C12A -2(2) . . . . ? C13A N4A C12A C11A -175.7(16) . . . . ? N3A N4A C12A C11A -0.5(18) . . . . ? C10A C11A C12A N4A 1.3(18) . . . . ? C12A N4A C13A C18A 176.3(15) . . . . ? N3A N4A C13A C18A 1(2) . . . . ? C12A N4A C13A C14A -3(3) . . . . ? N3A N4A C13A C14A -178.0(13) . . . . ? N4A C13A C14A C15A 178.0(14) . . . . ? C18A C13A C14A C15A -1(2) . . . . ? C13A C14A C15A C16A 1(2) . . . . ? C14A C15A C16A C17A 0(3) . . . . ? C15A C16A C17A C18A -2(2) . . . . ? C16A C17A C18A C13A 2(2) . . . . ? C16A C17A C18A Ir1A 177.4(12) . . . . ? N4A C13A C18A C17A -179.6(13) . . . . ? C14A C13A C18A C17A 0(2) . . . . ? N4A C13A C18A Ir1A 4.0(17) . . . . ? C14A C13A C18A Ir1A -176.8(12) . . . . ? N1A Ir1A C18A C17A 2.7(14) . . . . ? N3A Ir1A C18A C17A 178.8(15) . . . . ? C9A Ir1A C18A C17A 83.1(15) . . . . ? N5A Ir1A C18A C17A -93.2(14) . . . . ? N1A Ir1A C18A C13A 178.4(10) . . . . ? N3A Ir1A C18A C13A -5.5(10) . . . . ? C9A Ir1A C18A C13A -101.2(11) . . . . ? N5A Ir1A C18A C13A 82.4(11) . . . . ? Ir1A O1A C19A C24A -21(2) . . . . ? Ir1A O1A C19A C20A 159.5(12) . . . . ? O1A C19A C20A C21A 179.0(16) . . . . ? C24A C19A C20A C21A 0(3) . . . . ? C19A C20A C21A C22A 2(3) . . . . ? C20A C21A C22A C23A -3(3) . . . . ? C21A C22A C23A C24A 2(3) . . . . ? O1A C19A C24A C23A -179.9(16) . . . . ? C20A C19A C24A C23A -1(2) . . . . ? O1A C19A C24A C25A -3(3) . . . . ? C20A C19A C24A C25A 176.5(15) . . . . ? C22A C23A C24A C19A 0(3) . . . . ? C22A C23A C24A C25A -177.4(16) . . . . ? C27A N5A C25A O2A -6.6(19) . . . . ? Ir1A N5A C25A O2A 171.0(10) . . . . ? C27A N5A C25A C24A 169.5(16) . . . . ? Ir1A N5A C25A C24A -13(2) . . . . ? C26A O2A C25A N5A -11.5(19) . . . . ? C26A O2A C25A C24A 171.9(14) . . . . ? C19A C24A C25A N5A 22(3) . . . . ? C23A C24A C25A N5A -161.0(17) . . . . ? C19A C24A C25A O2A -162.1(14) . . . . ? C23A C24A C25A O2A 15(2) . . . . ? C25A O2A C26A C27A 23.6(17) . . . . ? C25A N5A C27A C26A 20.8(17) . . . . ? Ir1A N5A C27A C26A -156.9(11) . . . . ? C25A N5A C27A C28A -104.0(15) . . . . ? Ir1A N5A C27A C28A 78.3(15) . . . . ? O2A C26A C27A N5A -26.1(16) . . . . ? O2A C26A C27A C28A 95.0(16) . . . . ? N5A C27A C28A C30A 71.7(16) . . . . ? C26A C27A C28A C30A -44(2) . . . . ? N5A C27A C28A C29A -160.2(13) . . . . ? C26A C27A C28A C29A 84.4(18) . . . . ? N3B Ir1B O1B C19B 111.6(12) . . . . ? N1B Ir1B O1B C19B -73.1(12) . . . . ? C9B Ir1B O1B C19B -154.4(13) . . . . ? N5B Ir1B O1B C19B 23.9(12) . . . . ? C18B Ir1B N1B C1B -97.3(17) . . . . ? C9B Ir1B N1B C1B 172.7(17) . . . . ? O1B Ir1B N1B C1B 83.5(17) . . . . ? N5B Ir1B N1B C1B -1.8(17) . . . . ? C18B Ir1B N1B N2B 96.3(10) . . . . ? C9B Ir1B N1B N2B 6.3(10) . . . . ? O1B Ir1B N1B N2B -82.9(10) . . . . ? N5B Ir1B N1B N2B -168.2(10) . . . . ? C1B N1B N2B C3B -2.9(16) . . . . ? Ir1B N1B N2B C3B 167.9(9) . . . . ? C1B N1B N2B C4B -178.7(12) . . . . ? Ir1B N1B N2B C4B -8.0(16) . . . . ? C18B Ir1B N3B C10B 178.0(15) . . . . ? C9B Ir1B N3B C10B -91.1(15) . . . . ? O1B Ir1B N3B C10B -2.4(15) . . . . ? N5B Ir1B N3B C10B 83.4(15) . . . . ? C18B Ir1B N3B N4B 1.0(9) . . . . ? C9B Ir1B N3B N4B 91.9(10) . . . . ? O1B Ir1B N3B N4B -179.5(9) . . . . ? N5B Ir1B N3B N4B -93.6(9) . . . . ? C10B N3B N4B C12B 1.7(15) . . . . ? Ir1B N3B N4B C12B 179.6(9) . . . . ? C10B N3B N4B C13B 179.7(11) . . . . ? Ir1B N3B N4B C13B -2.4(14) . . . . ? C18B Ir1B N5B C25B 179.9(12) . . . . ? N3B Ir1B N5B C25B -99.7(12) . . . . ? N1B Ir1B N5B C25B 79.1(12) . . . . ? O1B Ir1B N5B C25B -4.4(12) . . . . ? C18B Ir1B N5B C27B -4.7(12) . . . . ? N3B Ir1B N5B C27B 75.7(12) . . . . ? N1B Ir1B N5B C27B -105.5(12) . . . . ? O1B Ir1B N5B C27B 171.0(12) . . . . ? N2B N1B C1B C2B 3.2(17) . . . . ? Ir1B N1B C1B C2B -163.7(13) . . . . ? N1B C1B C2B C3B -2.4(19) . . . . ? C4B N2B C3B C2B 176.2(15) . . . . ? N1B N2B C3B C2B 1.4(17) . . . . ? C1B C2B C3B N2B 0.5(18) . . . . ? C3B N2B C4B C5B 8(3) . . . . ? N1B N2B C4B C5B -177.7(14) . . . . ? C3B N2B C4B C9B -169.7(15) . . . . ? N1B N2B C4B C9B 4.7(19) . . . . ? N2B C4B C5B C6B -175.1(14) . . . . ? C9B C4B C5B C6B 2(2) . . . . ? C4B C5B C6B C7B 1(2) . . . . ? C5B C6B C7B C8B -3(3) . . . . ? C6B C7B C8B C9B 1(3) . . . . ? C7B C8B C9B C4B 2(2) . . . . ? C7B C8B C9B Ir1B 173.6(13) . . . . ? C5B C4B C9B C8B -3(2) . . . . ? N2B C4B C9B C8B 174.2(13) . . . . ? C5B C4B C9B Ir1B -176.8(12) . . . . ? N2B C4B C9B Ir1B 0.8(16) . . . . ? C18B Ir1B C9B C8B 83.7(15) . . . . ? N3B Ir1B C9B C8B 3.0(14) . . . . ? N1B Ir1B C9B C8B -176.2(15) . . . . ? O1B Ir1B C9B C8B -92.0(14) . . . . ? C18B Ir1B C9B C4B -104.1(11) . . . . ? N3B Ir1B C9B C4B 175.3(11) . . . . ? N1B Ir1B C9B C4B -4.0(10) . . . . ? O1B Ir1B C9B C4B 80.2(11) . . . . ? N4B N3B C10B C11B -2.3(16) . . . . ? Ir1B N3B C10B C11B -179.5(12) . . . . ? N3B C10B C11B C12B 2.1(19) . . . . ? N3B N4B C12B C11B -0.4(16) . . . . ? C13B N4B C12B C11B -177.9(14) . . . . ? C10B C11B C12B N4B -1.1(18) . . . . ? C12B N4B C13B C14B 0(2) . . . . ? N3B N4B C13B C14B -177.0(12) . . . . ? C12B N4B C13B C18B -179.9(14) . . . . ? N3B N4B C13B C18B 2.7(16) . . . . ? N4B C13B C14B C15B -179.5(14) . . . . ? C18B C13B C14B C15B 1(2) . . . . ? C13B C14B C15B C16B 0(3) . . . . ? C14B C15B C16B C17B 0(3) . . . . ? C15B C16B C17B C18B 0(3) . . . . ? C16B C17B C18B C13B 0(2) . . . . ? C16B C17B C18B Ir1B -177.9(12) . . . . ? C14B C13B C18B C17B -1(2) . . . . ? N4B C13B C18B C17B 179.5(11) . . . . ? C14B C13B C18B Ir1B 177.8(11) . . . . ? N4B C13B C18B Ir1B -1.9(15) . . . . ? N3B Ir1B C18B C17B 178.7(15) . . . . ? N1B Ir1B C18B C17B 3.4(15) . . . . ? C9B Ir1B C18B C17B 84.7(14) . . . . ? N5B Ir1B C18B C17B -94.0(14) . . . . ? N3B Ir1B C18B C13B 0.5(10) . . . . ? N1B Ir1B C18B C13B -174.7(10) . . . . ? C9B Ir1B C18B C13B -93.5(11) . . . . ? N5B Ir1B C18B C13B 87.8(11) . . . . ? Ir1B O1B C19B C20B 153.9(11) . . . . ? Ir1B O1B C19B C24B -25(2) . . . . ? O1B C19B C20B C21B 177.8(14) . . . . ? C24B C19B C20B C21B -3(2) . . . . ? C19B C20B C21B C22B 1(3) . . . . ? C20B C21B C22B C23B 0(3) . . . . ? C21B C22B C23B C24B 3(3) . . . . ? C22B C23B C24B C19B -5(2) . . . . ? C22B C23B C24B C25B 179.6(16) . . . . ? O1B C19B C24B C23B -175.4(14) . . . . ? C20B C19B C24B C23B 6(2) . . . . ? O1B C19B C24B C25B -1(2) . . . . ? C20B C19B C24B C25B -179.5(14) . . . . ? C27B N5B C25B O2B -8.5(17) . . . . ? Ir1B N5B C25B O2B 167.6(9) . . . . ? C27B N5B C25B C24B 167.4(14) . . . . ? Ir1B N5B C25B C24B -16(2) . . . . ? C26B O2B C25B N5B -8.3(17) . . . . ? C26B O2B C25B C24B 175.3(12) . . . . ? C23B C24B C25B N5B -161.5(15) . . . . ? C19B C24B C25B N5B 23(2) . . . . ? C23B C24B C25B O2B 14.3(19) . . . . ? C19B C24B C25B O2B -160.7(13) . . . . ? C25B O2B C26B C27B 20.7(15) . . . . ? C25B N5B C27B C28B -102.8(15) . . . . ? Ir1B N5B C27B C28B 81.1(15) . . . . ? C25B N5B C27B C26B 20.3(15) . . . . ? Ir1B N5B C27B C26B -155.8(10) . . . . ? O2B C26B C27B N5B -24.6(15) . . . . ? O2B C26B C27B C28B 97.0(15) . . . . ? N5B C27B C28B C30B 70.5(17) . . . . ? C26B C27B C28B C30B -44.5(19) . . . . ? N5B C27B C28B C29B -164.6(14) . . . . ? C26B C27B C28B C29B 80.4(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.252 _refine_diff_density_min -2.598 _refine_diff_density_rms 0.191 _database_code_depnum_ccdc_archive 'CCDC 922564' ####################################################################### # # 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_08014 #TrackingRef 'Shalini_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H30 Ir N3 O' _chemical_formula_sum 'C37 H30 Ir N3 O' _chemical_formula_weight 724.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1790(18) _cell_length_b 12.986(3) _cell_length_c 27.068(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2875.0(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1011 _cell_measurement_theta_min 3.481 _cell_measurement_theta_max 28.154 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 4.680 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.389 _exptl_absorpt_correction_T_max 0.604 _exptl_absorpt_process_details ; absorption correction based on 16785 reflections(SADABS);Rint 0.1021 before correction and 0.0480 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23997 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6235 _reflns_number_gt 5590 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(6) _refine_ls_number_reflns 6235 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0511 _refine_ls_wR_factor_gt 0.0498 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.74763(2) 1.049869(9) 0.363165(4) 0.02132(4) Uani 1 1 d . . . O1 O 0.6258(3) 1.0947(2) 0.29657(9) 0.0260(6) Uani 1 1 d . . . N1 N 0.9434(4) 1.0184(3) 0.31864(12) 0.0249(7) Uani 1 1 d . . . N2 N 0.5681(4) 1.0966(2) 0.40953(11) 0.0233(7) Uani 1 1 d . . . N3 N 0.6220(4) 0.9048(3) 0.35493(12) 0.0257(7) Uani 1 1 d . . . C1 C 0.9807(5) 0.9255(4) 0.29958(16) 0.0303(10) Uani 1 1 d . . . H1 H 0.9194 0.8672 0.3099 0.036 Uiso 1 1 calc R . . C2 C 1.1043(5) 0.9117(4) 0.26569(16) 0.0386(11) Uani 1 1 d . . . H2 H 1.1293 0.8452 0.2532 0.046 Uiso 1 1 calc R . . C3 C 1.1910(5) 0.9975(4) 0.25030(16) 0.0408(11) Uani 1 1 d . . . H3 H 1.2722 0.9912 0.2254 0.049 Uiso 1 1 calc R . . C4 C 1.1592(5) 1.0912(4) 0.27120(15) 0.0347(10) Uani 1 1 d . . . H4 H 1.2219 1.1496 0.2618 0.042 Uiso 1 1 calc R . . C5 C 1.0354(5) 1.1017(3) 0.30612(14) 0.0280(9) Uani 1 1 d . . . C6 C 0.9916(5) 1.1961(3) 0.33188(14) 0.0270(9) Uani 1 1 d . . . C7 C 1.0791(5) 1.2872(3) 0.32752(16) 0.0334(10) Uani 1 1 d . . . H7 H 1.1732 1.2894 0.3070 0.040 Uiso 1 1 calc R . . C8 C 1.0313(5) 1.3744(3) 0.35258(17) 0.0364(11) Uani 1 1 d . . . H8 H 1.0910 1.4368 0.3494 0.044 Uiso 1 1 calc R . . C9 C 0.8940(5) 1.3691(3) 0.38265(16) 0.0341(10) Uani 1 1 d . . . H9 H 0.8579 1.4290 0.3996 0.041 Uiso 1 1 calc R . . C10 C 0.8099(5) 1.2788(3) 0.38822(14) 0.0287(9) Uani 1 1 d . . . H10 H 0.7181 1.2771 0.4097 0.034 Uiso 1 1 calc R . . C11 C 0.8554(4) 1.1881(3) 0.36300(14) 0.0232(8) Uani 1 1 d . . . C12 C 0.4236(5) 1.1343(3) 0.39471(14) 0.0272(9) Uani 1 1 d . . . H12 H 0.3978 1.1330 0.3605 0.033 Uiso 1 1 calc R . . C13 C 0.3110(5) 1.1749(3) 0.42721(15) 0.0349(10) Uani 1 1 d . . . H13 H 0.2096 1.2013 0.4157 0.042 Uiso 1 1 calc R . . C14 C 0.3495(6) 1.1762(3) 0.47696(16) 0.0390(11) Uani 1 1 d . . . H14 H 0.2747 1.2044 0.5002 0.047 Uiso 1 1 calc R . . C15 C 0.4956(5) 1.1366(3) 0.49266(15) 0.0354(10) Uani 1 1 d . . . H15 H 0.5215 1.1370 0.5269 0.042 Uiso 1 1 calc R . . C16 C 0.6068(5) 1.0958(3) 0.45887(14) 0.0274(9) Uani 1 1 d . . . C17 C 0.7690(5) 1.0531(3) 0.46969(12) 0.0254(8) Uani 1 1 d . . . C18 C 0.8320(5) 1.0436(3) 0.51724(15) 0.0351(10) Uani 1 1 d . . . H18 H 0.7695 1.0650 0.5450 0.042 Uiso 1 1 calc R . . C19 C 0.9873(6) 1.0025(4) 0.52361(16) 0.0415(12) Uani 1 1 d . . . H19 H 1.0311 0.9950 0.5559 0.050 Uiso 1 1 calc R . . C20 C 1.0776(6) 0.9725(4) 0.48341(17) 0.0409(12) Uani 1 1 d . . . H20 H 1.1841 0.9449 0.4881 0.049 Uiso 1 1 calc R . . C21 C 1.0152(5) 0.9821(3) 0.43604(16) 0.0334(10) Uani 1 1 d . . . H21 H 1.0795 0.9606 0.4087 0.040 Uiso 1 1 calc R . . C22 C 0.8582(5) 1.0230(3) 0.42774(14) 0.0255(9) Uani 1 1 d . . . C23 C 0.6032(4) 1.0305(3) 0.26072(14) 0.0250(9) Uani 1 1 d . . . C24 C 0.6062(5) 1.0684(3) 0.21134(14) 0.0302(10) Uani 1 1 d . . . H24 H 0.6317 1.1388 0.2058 0.036 Uiso 1 1 calc R . . C25 C 0.5733(5) 1.0062(3) 0.17165(15) 0.0333(10) Uani 1 1 d . . . H25 H 0.5792 1.0339 0.1392 0.040 Uiso 1 1 calc R . . C26 C 0.5317(5) 0.9037(4) 0.17814(16) 0.0331(10) Uani 1 1 d . . . H26 H 0.5052 0.8618 0.1505 0.040 Uiso 1 1 calc R . . C27 C 0.5293(4) 0.8634(3) 0.22502(14) 0.0297(9) Uani 1 1 d . . . H27 H 0.5006 0.7932 0.2296 0.036 Uiso 1 1 calc R . . C28 C 0.5686(4) 0.9245(3) 0.26646(14) 0.0220(8) Uani 1 1 d . . . C29 C 0.5602(5) 0.8743(3) 0.31388(15) 0.0262(9) Uani 1 1 d . . . H29 H 0.5021 0.8110 0.3149 0.031 Uiso 1 1 calc R . . C30 C 0.6036(5) 0.8365(3) 0.39926(14) 0.0289(9) Uani 1 1 d . . . H30 H 0.6068 0.8825 0.4289 0.035 Uiso 1 1 calc R . . C31 C 0.4418(5) 0.7784(3) 0.40162(16) 0.0391(11) Uani 1 1 d . . . H31A H 0.3510 0.8271 0.3981 0.059 Uiso 1 1 calc R . . H31B H 0.4331 0.7429 0.4335 0.059 Uiso 1 1 calc R . . H31C H 0.4373 0.7278 0.3748 0.059 Uiso 1 1 calc R . . C32 C 0.7500(7) 0.7655(2) 0.40323(12) 0.0321(8) Uani 1 1 d . . . C33 C 0.8009(5) 0.7045(3) 0.36370(17) 0.0411(12) Uani 1 1 d . . . H33 H 0.7400 0.7056 0.3338 0.049 Uiso 1 1 calc R . . C34 C 0.9376(6) 0.6423(4) 0.36693(17) 0.0478(12) Uani 1 1 d . . . H34 H 0.9720 0.6033 0.3391 0.057 Uiso 1 1 calc R . . C35 C 1.0241(6) 0.6371(4) 0.41062(19) 0.0471(12) Uani 1 1 d . . . H35 H 1.1191 0.5953 0.4131 0.057 Uiso 1 1 calc R . . C36 C 0.9706(6) 0.6934(4) 0.45062(17) 0.0432(12) Uani 1 1 d . . . H36 H 1.0264 0.6879 0.4813 0.052 Uiso 1 1 calc R . . C37 C 0.8378(6) 0.7574(4) 0.44680(15) 0.0371(10) Uani 1 1 d . . . H37 H 0.8053 0.7970 0.4746 0.045 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 0.02372(7) 0.02265(7) 0.01760(6) -0.00036(5) 0.00062(12) -0.00285(11) O1 0.0331(15) 0.0262(14) 0.0187(14) -0.0038(12) -0.0048(12) 0.0007(12) N1 0.0258(17) 0.0307(19) 0.0181(16) -0.0013(14) 0.0000(14) -0.0001(14) N2 0.0261(17) 0.0269(17) 0.0169(16) -0.0017(14) 0.0039(14) -0.0073(14) N3 0.0276(17) 0.0253(17) 0.0242(18) -0.0012(15) -0.0003(14) -0.0022(14) C1 0.025(2) 0.032(3) 0.034(3) -0.003(2) -0.0036(19) 0.0014(18) C2 0.028(2) 0.054(3) 0.034(2) -0.012(2) -0.0061(19) 0.012(2) C3 0.029(2) 0.065(3) 0.028(2) 0.002(2) -0.0014(18) 0.009(2) C4 0.027(2) 0.049(3) 0.029(2) 0.008(2) 0.0003(18) 0.000(2) C5 0.024(2) 0.038(2) 0.023(2) 0.0079(18) -0.0027(16) -0.0037(17) C6 0.024(2) 0.033(2) 0.024(2) 0.0067(18) -0.0027(16) -0.0038(17) C7 0.026(2) 0.038(3) 0.037(3) 0.009(2) 0.0004(19) -0.0066(18) C8 0.036(2) 0.029(3) 0.044(3) 0.008(2) -0.010(2) -0.0089(18) C9 0.045(3) 0.026(2) 0.032(2) 0.0026(19) -0.012(2) -0.0035(19) C10 0.037(2) 0.028(2) 0.021(2) 0.0002(17) -0.0061(16) -0.0054(16) C11 0.0262(19) 0.028(2) 0.0152(18) 0.0054(17) -0.0035(16) -0.0032(15) C12 0.034(2) 0.025(2) 0.023(2) -0.0002(17) -0.0009(17) -0.0050(17) C13 0.032(2) 0.035(3) 0.038(2) -0.0008(19) 0.0071(18) -0.0007(17) C14 0.043(3) 0.039(3) 0.036(3) -0.004(2) 0.014(2) 0.000(2) C15 0.051(3) 0.035(3) 0.020(2) -0.0013(19) 0.0096(19) -0.005(2) C16 0.035(2) 0.025(2) 0.022(2) 0.0030(17) 0.0014(18) -0.0084(18) C17 0.027(2) 0.0276(18) 0.0217(16) 0.0019(14) -0.0036(18) -0.007(2) C18 0.043(2) 0.040(3) 0.022(2) 0.003(2) -0.0025(18) -0.013(2) C19 0.051(3) 0.049(3) 0.024(2) 0.012(2) -0.010(2) -0.014(2) C20 0.033(2) 0.047(3) 0.043(3) 0.010(2) -0.014(2) -0.006(2) C21 0.033(2) 0.036(3) 0.031(2) 0.0003(19) -0.0001(19) -0.0069(18) C22 0.030(2) 0.027(2) 0.020(2) 0.0009(16) -0.0061(17) -0.0100(16) C23 0.0151(17) 0.034(2) 0.026(2) -0.0019(18) 0.0023(15) 0.0045(16) C24 0.034(2) 0.032(3) 0.025(2) 0.0008(18) -0.0037(17) 0.0030(18) C25 0.035(2) 0.042(3) 0.023(2) 0.000(2) 0.0000(18) 0.010(2) C26 0.035(2) 0.041(3) 0.023(2) -0.014(2) -0.0032(19) 0.009(2) C27 0.026(2) 0.032(2) 0.031(2) -0.0058(19) -0.0029(17) 0.0063(18) C28 0.0210(18) 0.026(2) 0.019(2) -0.0063(16) -0.0023(16) 0.0043(15) C29 0.027(2) 0.024(2) 0.027(2) -0.0057(18) -0.0012(18) -0.0024(17) C30 0.033(2) 0.033(2) 0.020(2) 0.0000(18) 0.0053(17) -0.0047(18) C31 0.045(3) 0.039(3) 0.033(3) 0.003(2) 0.005(2) -0.012(2) C32 0.044(2) 0.0245(17) 0.0280(18) 0.0065(14) -0.010(3) -0.009(3) C33 0.062(3) 0.023(2) 0.038(2) -0.0029(19) -0.017(2) 0.0053(18) C34 0.075(3) 0.027(2) 0.041(3) -0.006(2) -0.008(3) 0.012(2) C35 0.053(3) 0.032(3) 0.057(3) 0.004(2) -0.014(3) 0.004(2) C36 0.049(3) 0.049(3) 0.031(3) 0.004(2) -0.013(2) -0.002(2) C37 0.048(3) 0.041(3) 0.023(2) 0.004(2) 0.0001(19) -0.010(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 C22 1.999(4) . ? Ir1 C11 1.999(4) . ? Ir1 N2 2.025(3) . ? Ir1 N1 2.045(3) . ? Ir1 O1 2.140(3) . ? Ir1 N3 2.157(3) . ? O1 C23 1.293(4) . ? N1 C1 1.348(5) . ? N1 C5 1.360(5) . ? N2 C12 1.341(5) . ? N2 C16 1.372(5) . ? N3 C29 1.283(5) . ? N3 C30 1.500(5) . ? C1 C2 1.376(6) . ? C1 H1 0.9500 . ? C2 C3 1.385(6) . ? C2 H2 0.9500 . ? C3 C4 1.368(6) . ? C3 H3 0.9500 . ? C4 C5 1.391(5) . ? C4 H4 0.9500 . ? C5 C6 1.456(6) . ? C6 C7 1.387(5) . ? C6 C11 1.401(5) . ? C7 C8 1.377(6) . ? C7 H7 0.9500 . ? C8 C9 1.389(6) . ? C8 H8 0.9500 . ? C9 C10 1.368(5) . ? C9 H9 0.9500 . ? C10 C11 1.412(5) . ? C10 H10 0.9500 . ? C12 C13 1.378(5) . ? C12 H12 0.9500 . ? C13 C14 1.383(6) . ? C13 H13 0.9500 . ? C14 C15 1.368(6) . ? C14 H14 0.9500 . ? C15 C16 1.395(5) . ? C15 H15 0.9500 . ? C16 C17 1.468(5) . ? C17 C18 1.391(5) . ? C17 C22 1.405(5) . ? C18 C19 1.389(6) . ? C18 H18 0.9500 . ? C19 C20 1.372(6) . ? C19 H19 0.9500 . ? C20 C21 1.386(6) . ? C20 H20 0.9500 . ? C21 C22 1.408(6) . ? C21 H21 0.9500 . ? C23 C28 1.413(5) . ? C23 C24 1.425(5) . ? C24 C25 1.370(6) . ? C24 H24 0.9500 . ? C25 C26 1.385(6) . ? C25 H25 0.9500 . ? C26 C27 1.373(6) . ? C26 H26 0.9500 . ? C27 C28 1.411(5) . ? C27 H27 0.9500 . ? C28 C29 1.441(5) . ? C29 H29 0.9500 . ? C30 C32 1.516(6) . ? C30 C31 1.525(5) . ? C30 H30 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C37 1.385(6) . ? C32 C33 1.395(6) . ? C33 C34 1.382(6) . ? C33 H33 0.9500 . ? C34 C35 1.380(6) . ? C34 H34 0.9500 . ? C35 C36 1.378(7) . ? C35 H35 0.9500 . ? C36 C37 1.371(6) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? 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 C11 87.67(15) . . ? C22 Ir1 N2 80.70(14) . . ? C11 Ir1 N2 92.99(14) . . ? C22 Ir1 N1 97.26(15) . . ? C11 Ir1 N1 80.36(14) . . ? N2 Ir1 N1 173.15(12) . . ? C22 Ir1 O1 174.08(13) . . ? C11 Ir1 O1 87.67(13) . . ? N2 Ir1 O1 95.91(12) . . ? N1 Ir1 O1 85.55(11) . . ? C22 Ir1 N3 98.83(14) . . ? C11 Ir1 N3 173.46(14) . . ? N2 Ir1 N3 88.87(13) . . ? N1 Ir1 N3 97.92(12) . . ? O1 Ir1 N3 85.90(11) . . ? C23 O1 Ir1 121.6(2) . . ? C1 N1 C5 119.4(3) . . ? C1 N1 Ir1 125.6(3) . . ? C5 N1 Ir1 114.9(3) . . ? C12 N2 C16 119.8(3) . . ? C12 N2 Ir1 124.3(3) . . ? C16 N2 Ir1 115.7(3) . . ? C29 N3 C30 118.1(3) . . ? C29 N3 Ir1 123.1(3) . . ? C30 N3 Ir1 118.8(2) . . ? N1 C1 C2 122.5(4) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 118.2(4) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 119.6(4) . . ? N1 C5 C6 114.5(3) . . ? C4 C5 C6 125.9(4) . . ? C7 C6 C11 121.7(4) . . ? C7 C6 C5 123.4(4) . . ? C11 C6 C5 114.9(4) . . ? C8 C7 C6 120.9(4) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 118.5(4) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C10 C9 C8 120.9(4) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 122.0(4) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C6 C11 C10 116.0(4) . . ? C6 C11 Ir1 114.8(3) . . ? C10 C11 Ir1 129.2(3) . . ? N2 C12 C13 122.5(4) . . ? N2 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C14 118.3(4) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.6(4) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? N2 C16 C15 119.0(4) . . ? N2 C16 C17 114.0(3) . . ? C15 C16 C17 127.0(4) . . ? C18 C17 C22 122.1(4) . . ? C18 C17 C16 123.5(4) . . ? C22 C17 C16 114.4(3) . . ? C19 C18 C17 119.2(4) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C20 C19 C18 120.2(4) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 120.7(4) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C20 C21 C22 121.2(4) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C17 C22 C21 116.7(4) . . ? C17 C22 Ir1 115.1(3) . . ? C21 C22 Ir1 128.2(3) . . ? O1 C23 C28 125.0(4) . . ? O1 C23 C24 118.6(4) . . ? C28 C23 C24 116.3(4) . . ? C25 C24 C23 121.9(4) . . ? C25 C24 H24 119.0 . . ? C23 C24 H24 119.0 . . ? C24 C25 C26 121.0(4) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C27 C26 C25 119.1(4) . . ? C27 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? C26 C27 C28 121.2(4) . . ? C26 C27 H27 119.4 . . ? C28 C27 H27 119.4 . . ? C27 C28 C23 120.4(4) . . ? C27 C28 C29 116.3(4) . . ? C23 C28 C29 123.2(3) . . ? N3 C29 C28 127.8(4) . . ? N3 C29 H29 116.1 . . ? C28 C29 H29 116.1 . . ? N3 C30 C32 109.7(3) . . ? N3 C30 C31 114.4(3) . . ? C32 C30 C31 112.4(4) . . ? N3 C30 H30 106.6 . . ? C32 C30 H30 106.6 . . ? C31 C30 H30 106.6 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C37 C32 C33 117.1(5) . . ? C37 C32 C30 121.1(4) . . ? C33 C32 C30 121.8(4) . . ? C34 C33 C32 121.6(4) . . ? C34 C33 H33 119.2 . . ? C32 C33 H33 119.2 . . ? C35 C34 C33 119.9(5) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C36 C35 C34 119.0(5) . . ? C36 C35 H35 120.5 . . ? C34 C35 H35 120.5 . . ? C37 C36 C35 120.9(4) . . ? C37 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? C36 C37 C32 121.4(4) . . ? C36 C37 H37 119.3 . . ? C32 C37 H37 119.3 . . ? 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 C11 Ir1 O1 C23 141.0(3) . . . . ? N2 Ir1 O1 C23 -126.2(3) . . . . ? N1 Ir1 O1 C23 60.5(3) . . . . ? N3 Ir1 O1 C23 -37.8(3) . . . . ? C22 Ir1 N1 C1 90.2(3) . . . . ? C11 Ir1 N1 C1 176.5(3) . . . . ? O1 Ir1 N1 C1 -95.1(3) . . . . ? N3 Ir1 N1 C1 -9.8(3) . . . . ? C22 Ir1 N1 C5 -93.4(3) . . . . ? C11 Ir1 N1 C5 -7.0(3) . . . . ? O1 Ir1 N1 C5 81.4(3) . . . . ? N3 Ir1 N1 C5 166.6(3) . . . . ? C22 Ir1 N2 C12 179.3(3) . . . . ? C11 Ir1 N2 C12 92.1(3) . . . . ? O1 Ir1 N2 C12 4.2(3) . . . . ? N3 Ir1 N2 C12 -81.6(3) . . . . ? C22 Ir1 N2 C16 4.5(3) . . . . ? C11 Ir1 N2 C16 -82.6(3) . . . . ? O1 Ir1 N2 C16 -170.6(3) . . . . ? N3 Ir1 N2 C16 103.6(3) . . . . ? C22 Ir1 N3 C29 -164.5(3) . . . . ? N2 Ir1 N3 C29 115.1(3) . . . . ? N1 Ir1 N3 C29 -65.9(3) . . . . ? O1 Ir1 N3 C29 19.1(3) . . . . ? C22 Ir1 N3 C30 16.3(3) . . . . ? N2 Ir1 N3 C30 -64.2(3) . . . . ? N1 Ir1 N3 C30 114.9(3) . . . . ? O1 Ir1 N3 C30 -160.2(3) . . . . ? C5 N1 C1 C2 -3.4(6) . . . . ? Ir1 N1 C1 C2 172.9(3) . . . . ? N1 C1 C2 C3 -1.0(6) . . . . ? C1 C2 C3 C4 4.1(6) . . . . ? C2 C3 C4 C5 -2.9(6) . . . . ? C1 N1 C5 C4 4.5(6) . . . . ? Ir1 N1 C5 C4 -172.1(3) . . . . ? C1 N1 C5 C6 -175.4(4) . . . . ? Ir1 N1 C5 C6 7.9(4) . . . . ? C3 C4 C5 N1 -1.5(6) . . . . ? C3 C4 C5 C6 178.5(4) . . . . ? N1 C5 C6 C7 174.4(4) . . . . ? C4 C5 C6 C7 -5.6(6) . . . . ? N1 C5 C6 C11 -3.9(5) . . . . ? C4 C5 C6 C11 176.1(4) . . . . ? C11 C6 C7 C8 -2.2(6) . . . . ? C5 C6 C7 C8 179.6(4) . . . . ? C6 C7 C8 C9 0.4(6) . . . . ? C7 C8 C9 C10 1.5(6) . . . . ? C8 C9 C10 C11 -1.6(6) . . . . ? C7 C6 C11 C10 2.0(6) . . . . ? C5 C6 C11 C10 -179.7(3) . . . . ? C7 C6 C11 Ir1 179.7(3) . . . . ? C5 C6 C11 Ir1 -2.0(4) . . . . ? C9 C10 C11 C6 -0.1(6) . . . . ? C9 C10 C11 Ir1 -177.4(3) . . . . ? C22 Ir1 C11 C6 102.5(3) . . . . ? N2 Ir1 C11 C6 -176.9(3) . . . . ? N1 Ir1 C11 C6 4.7(3) . . . . ? O1 Ir1 C11 C6 -81.1(3) . . . . ? C22 Ir1 C11 C10 -80.2(4) . . . . ? N2 Ir1 C11 C10 0.4(4) . . . . ? N1 Ir1 C11 C10 -178.0(4) . . . . ? O1 Ir1 C11 C10 96.2(3) . . . . ? C16 N2 C12 C13 1.3(6) . . . . ? Ir1 N2 C12 C13 -173.3(3) . . . . ? N2 C12 C13 C14 -0.2(6) . . . . ? C12 C13 C14 C15 -0.7(6) . . . . ? C13 C14 C15 C16 0.5(7) . . . . ? C12 N2 C16 C15 -1.4(6) . . . . ? Ir1 N2 C16 C15 173.6(3) . . . . ? C12 N2 C16 C17 -179.6(3) . . . . ? Ir1 N2 C16 C17 -4.5(4) . . . . ? C14 C15 C16 N2 0.5(6) . . . . ? C14 C15 C16 C17 178.4(4) . . . . ? N2 C16 C17 C18 -179.0(4) . . . . ? C15 C16 C17 C18 3.0(7) . . . . ? N2 C16 C17 C22 1.5(5) . . . . ? C15 C16 C17 C22 -176.4(4) . . . . ? C22 C17 C18 C19 -0.4(6) . . . . ? C16 C17 C18 C19 -179.8(4) . . . . ? C17 C18 C19 C20 0.6(7) . . . . ? C18 C19 C20 C21 -0.5(7) . . . . ? C19 C20 C21 C22 0.2(7) . . . . ? C18 C17 C22 C21 0.2(6) . . . . ? C16 C17 C22 C21 179.6(3) . . . . ? C18 C17 C22 Ir1 -177.2(3) . . . . ? C16 C17 C22 Ir1 2.2(4) . . . . ? C20 C21 C22 C17 -0.1(6) . . . . ? C20 C21 C22 Ir1 177.0(3) . . . . ? C11 Ir1 C22 C17 89.9(3) . . . . ? N2 Ir1 C22 C17 -3.6(3) . . . . ? N1 Ir1 C22 C17 169.8(3) . . . . ? N3 Ir1 C22 C17 -90.9(3) . . . . ? C11 Ir1 C22 C21 -87.2(4) . . . . ? N2 Ir1 C22 C21 179.4(4) . . . . ? N1 Ir1 C22 C21 -7.3(4) . . . . ? N3 Ir1 C22 C21 92.0(4) . . . . ? Ir1 O1 C23 C28 36.0(5) . . . . ? Ir1 O1 C23 C24 -146.8(3) . . . . ? O1 C23 C24 C25 -175.9(4) . . . . ? C28 C23 C24 C25 1.5(6) . . . . ? C23 C24 C25 C26 1.6(6) . . . . ? C24 C25 C26 C27 -2.3(6) . . . . ? C25 C26 C27 C28 -0.1(6) . . . . ? C26 C27 C28 C23 3.3(6) . . . . ? C26 C27 C28 C29 179.4(4) . . . . ? O1 C23 C28 C27 173.4(4) . . . . ? C24 C23 C28 C27 -3.9(5) . . . . ? O1 C23 C28 C29 -2.4(6) . . . . ? C24 C23 C28 C29 -179.7(4) . . . . ? C30 N3 C29 C28 -177.2(4) . . . . ? Ir1 N3 C29 C28 3.5(6) . . . . ? C27 C28 C29 N3 163.8(4) . . . . ? C23 C28 C29 N3 -20.3(6) . . . . ? C29 N3 C30 C32 91.8(4) . . . . ? Ir1 N3 C30 C32 -89.0(3) . . . . ? C29 N3 C30 C31 -35.7(5) . . . . ? Ir1 N3 C30 C31 143.6(3) . . . . ? N3 C30 C32 C37 128.4(4) . . . . ? C31 C30 C32 C37 -103.1(5) . . . . ? N3 C30 C32 C33 -52.7(5) . . . . ? C31 C30 C32 C33 75.9(5) . . . . ? C37 C32 C33 C34 -3.1(7) . . . . ? C30 C32 C33 C34 177.9(4) . . . . ? C32 C33 C34 C35 2.2(8) . . . . ? C33 C34 C35 C36 0.8(8) . . . . ? C34 C35 C36 C37 -2.9(8) . . . . ? C35 C36 C37 C32 1.9(7) . . . . ? C33 C32 C37 C36 1.1(7) . . . . ? C30 C32 C37 C36 -179.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.824 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 922565' ####################################################################### # # 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_08016 #TrackingRef 'Shalini_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C37 H30 N3 O Ir)2.5(C H4 O)' _chemical_formula_sum 'C39.50 H40 Ir N3 O3.50' _chemical_formula_weight 804.95 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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.541(2) _cell_length_b 12.508(3) _cell_length_c 28.060(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3348.8(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 977 _cell_measurement_theta_min 3.258 _cell_measurement_theta_max 27.550 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1612 _exptl_absorpt_coefficient_mu 4.032 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details ; absorption correction based on 20098 reflections(SADABS);Rint 0.0845 before correction and 0.0560 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25945 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6587 _reflns_number_gt 6338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.026(10) _refine_ls_number_reflns 6587 _refine_ls_number_parameters 440 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.246 _refine_ls_restrained_S_all 1.246 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.95428(2) 0.585984(19) 0.373865(10) 0.02023(7) Uani 1 1 d . . . O1 O 0.8533(5) 0.4363(3) 0.35942(15) 0.0239(10) Uani 1 1 d . . . N1 N 0.7824(6) 0.6514(4) 0.40584(19) 0.0201(12) Uani 1 1 d . . . N2 N 1.1397(6) 0.5265(4) 0.3492(2) 0.0235(12) Uani 1 1 d . . . N3 N 0.8881(6) 0.6401(4) 0.30542(19) 0.0205(12) Uani 1 1 d . . . C1 C 0.6538(7) 0.6071(5) 0.4053(3) 0.0279(16) Uani 1 1 d . . . H1 H 0.6403 0.5418 0.3885 0.034 Uiso 1 1 calc R . . C2 C 0.5412(8) 0.6530(6) 0.4281(2) 0.0330(16) Uani 1 1 d . . . H2 H 0.4507 0.6216 0.4260 0.040 Uiso 1 1 calc R . . C3 C 0.5619(8) 0.7455(6) 0.4541(3) 0.0340(17) Uani 1 1 d . . . H3 H 0.4864 0.7777 0.4709 0.041 Uiso 1 1 calc R . . C4 C 0.6961(7) 0.7911(6) 0.4555(2) 0.0280(16) Uani 1 1 d . . . H4 H 0.7130 0.8537 0.4738 0.034 Uiso 1 1 calc R . . C5 C 0.8040(7) 0.7439(5) 0.4298(2) 0.0237(14) Uani 1 1 d . . . C6 C 0.9453(7) 0.7864(5) 0.4250(2) 0.0221(13) Uani 1 1 d . . . C7 C 0.9889(8) 0.8832(6) 0.4445(3) 0.0317(18) Uani 1 1 d . . . H7 H 0.9255 0.9251 0.4628 0.038 Uiso 1 1 calc R . . C8 C 1.1254(8) 0.9185(6) 0.4372(3) 0.0370(17) Uani 1 1 d . . . H8 H 1.1560 0.9840 0.4508 0.044 Uiso 1 1 calc R . . C9 C 1.2157(9) 0.8579(6) 0.4102(3) 0.0357(19) Uani 1 1 d . . . H9 H 1.3084 0.8828 0.4049 0.043 Uiso 1 1 calc R . . C10 C 1.1741(7) 0.7609(6) 0.3905(3) 0.0308(17) Uani 1 1 d . . . H10 H 1.2391 0.7198 0.3726 0.037 Uiso 1 1 calc R . . C11 C 1.0373(8) 0.7234(5) 0.3971(2) 0.0244(14) Uani 1 1 d . . . C12 C 1.1829(8) 0.5316(6) 0.3029(3) 0.0300(17) Uani 1 1 d . . . H12 H 1.1225 0.5626 0.2798 0.036 Uiso 1 1 calc R . . C13 C 1.3118(7) 0.4929(6) 0.2886(3) 0.0308(17) Uani 1 1 d . . . H13 H 1.3407 0.4990 0.2563 0.037 Uiso 1 1 calc R . . C14 C 1.3971(8) 0.4459(6) 0.3215(3) 0.0334(18) Uani 1 1 d . . . H14 H 1.4861 0.4189 0.3123 0.040 Uiso 1 1 calc R . . C15 C 1.3533(8) 0.4376(5) 0.3687(3) 0.0361(17) Uani 1 1 d . . . H15 H 1.4114 0.4035 0.3916 0.043 Uiso 1 1 calc R . . C16 C 1.2237(7) 0.4795(5) 0.3821(3) 0.0257(16) Uani 1 1 d . . . C17 C 1.1640(7) 0.4756(5) 0.4296(3) 0.0297(17) Uani 1 1 d . . . C18 C 1.2297(9) 0.4265(6) 0.4682(3) 0.0388(19) Uani 1 1 d . . . H18 H 1.3190 0.3941 0.4642 0.047 Uiso 1 1 calc R . . C19 C 1.1653(9) 0.4250(6) 0.5122(3) 0.0408(19) Uani 1 1 d . . . H19 H 1.2122 0.3947 0.5388 0.049 Uiso 1 1 calc R . . C20 C 1.0313(9) 0.4680(6) 0.5176(3) 0.0373(18) Uani 1 1 d . . . H20 H 0.9850 0.4640 0.5476 0.045 Uiso 1 1 calc R . . C21 C 0.9656(8) 0.5170(5) 0.4790(2) 0.0303(15) Uani 1 1 d . . . H21 H 0.8757 0.5481 0.4833 0.036 Uiso 1 1 calc R . . C22 C 1.0278(7) 0.5215(5) 0.4344(2) 0.0232(14) Uani 1 1 d . . . C23 C 0.7872(6) 0.4081(6) 0.3199(2) 0.0276(15) Uani 1 1 d . . . C24 C 0.7316(7) 0.3031(5) 0.3172(3) 0.0261(16) Uani 1 1 d . . . H24 H 0.7392 0.2576 0.3441 0.031 Uiso 1 1 calc R . . C25 C 0.6678(7) 0.2652(6) 0.2773(3) 0.0334(17) Uani 1 1 d . . . H25 H 0.6320 0.1944 0.2769 0.040 Uiso 1 1 calc R . . C26 C 0.6545(8) 0.3292(6) 0.2370(3) 0.0363(18) Uani 1 1 d . . . H26 H 0.6122 0.3021 0.2088 0.044 Uiso 1 1 calc R . . C27 C 0.7037(7) 0.4325(6) 0.2388(3) 0.0315(17) Uani 1 1 d . . . H27 H 0.6927 0.4770 0.2116 0.038 Uiso 1 1 calc R . . C28 C 0.7702(7) 0.4748(5) 0.2798(2) 0.0244(15) Uani 1 1 d . . . C29 C 0.8193(6) 0.5853(6) 0.2751(2) 0.0230(13) Uani 1 1 d . . . H29 H 0.7973 0.6202 0.2460 0.028 Uiso 1 1 calc R . . C30 C 0.9348(7) 0.7500(5) 0.2896(2) 0.0256(14) Uani 1 1 d . . . H30 H 1.0341 0.7581 0.3005 0.031 Uiso 1 1 calc R . . C31 C 0.9356(8) 0.7684(6) 0.2359(2) 0.0304(16) Uani 1 1 d . . . H31A H 0.9921 0.7130 0.2204 0.046 Uiso 1 1 calc R . . H31B H 0.9758 0.8388 0.2290 0.046 Uiso 1 1 calc R . . H31C H 0.8394 0.7653 0.2238 0.046 Uiso 1 1 calc R . . C32 C 0.8518(8) 0.8384(5) 0.3139(2) 0.0241(14) Uani 1 1 d . . . C33 C 0.7098(7) 0.8291(6) 0.3231(2) 0.0267(15) Uani 1 1 d . . . H33 H 0.6619 0.7646 0.3158 0.032 Uiso 1 1 calc R . . C34 C 0.6374(8) 0.9149(6) 0.3433(2) 0.0330(15) Uani 1 1 d . . . H34 H 0.5409 0.9078 0.3510 0.040 Uiso 1 1 calc R . . C35 C 0.7052(9) 1.0092(6) 0.3519(2) 0.0326(18) Uani 1 1 d . . . H35 H 0.6548 1.0684 0.3644 0.039 Uiso 1 1 calc R . . C36 C 0.8460(9) 1.0187(6) 0.3426(3) 0.0329(17) Uani 1 1 d . . . H36 H 0.8930 1.0839 0.3494 0.040 Uiso 1 1 calc R . . C37 C 0.9197(7) 0.9341(5) 0.3232(2) 0.0290(16) Uani 1 1 d . . . H37 H 1.0167 0.9415 0.3163 0.035 Uiso 1 1 calc R . . C38 C 0.9769(12) 0.2279(8) 0.4315(3) 0.062(3) Uani 1 1 d . . . H38A H 1.0229 0.2744 0.4548 0.093 Uiso 1 1 calc R . . H38B H 1.0083 0.1540 0.4362 0.093 Uiso 1 1 calc R . . H38C H 0.8751 0.2318 0.4357 0.093 Uiso 1 1 calc R . . O2 O 1.0130(6) 0.2622(5) 0.3841(2) 0.0528(16) Uani 1 1 d . . . H2A H 0.9514 0.3045 0.3739 0.079 Uiso 1 1 calc R . . C39 C 0.632(4) 0.356(2) 0.4674(8) 0.114(12) Uani 0.50 1 d P . . H39A H 0.7229 0.3481 0.4834 0.170 Uiso 0.50 1 calc PR . . H39B H 0.5650 0.3054 0.4810 0.170 Uiso 0.50 1 calc PR . . H39C H 0.5978 0.4291 0.4717 0.170 Uiso 0.50 1 calc PR . . O3 O 0.648(3) 0.3353(16) 0.4191(7) 0.117(8) Uani 0.50 1 d P . . H3A H 0.7007 0.2819 0.4155 0.175 Uiso 0.50 1 calc PR . . C40 C 0.3407(12) 0.1478(9) 0.3757(6) 0.096(4) Uani 1 1 d . . . H40A H 0.4113 0.1965 0.3625 0.145 Uiso 1 1 calc R . . H40B H 0.3822 0.0769 0.3803 0.145 Uiso 1 1 calc R . . H40C H 0.3079 0.1754 0.4065 0.145 Uiso 1 1 calc R . . O4 O 0.2286(11) 0.1404(10) 0.3445(3) 0.111(4) Uani 1 1 d . . . H4A H 0.1579 0.1696 0.3567 0.166 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 0.01628(11) 0.01705(11) 0.02736(12) -0.00280(12) 0.00072(12) 0.00114(10) O1 0.025(2) 0.015(2) 0.032(3) -0.0010(17) -0.0015(19) -0.0029(18) N1 0.022(3) 0.018(3) 0.020(3) -0.008(2) 0.004(2) 0.001(2) N2 0.019(3) 0.016(3) 0.036(3) 0.004(2) 0.004(3) 0.000(2) N3 0.017(3) 0.024(3) 0.021(3) -0.003(2) 0.006(2) 0.000(2) C1 0.022(3) 0.026(4) 0.036(4) -0.004(3) 0.005(3) -0.004(3) C2 0.022(4) 0.040(4) 0.037(4) 0.001(3) 0.001(4) -0.004(4) C3 0.029(4) 0.034(4) 0.040(4) -0.007(3) 0.011(3) 0.008(3) C4 0.033(4) 0.028(4) 0.023(4) -0.003(3) 0.000(3) 0.005(3) C5 0.028(4) 0.018(3) 0.024(4) 0.004(3) 0.002(3) 0.002(3) C6 0.022(3) 0.023(3) 0.021(3) -0.001(2) -0.005(3) 0.001(3) C7 0.039(4) 0.025(4) 0.030(4) -0.001(3) -0.009(3) 0.002(3) C8 0.039(4) 0.022(3) 0.050(5) -0.009(4) -0.007(4) -0.001(4) C9 0.026(4) 0.033(4) 0.048(5) 0.002(4) -0.005(4) -0.004(3) C10 0.026(4) 0.024(4) 0.043(4) -0.001(3) 0.001(3) 0.001(3) C11 0.022(3) 0.016(3) 0.035(3) -0.001(3) -0.006(3) 0.000(3) C12 0.032(4) 0.023(4) 0.035(4) -0.006(3) 0.002(3) -0.002(3) C13 0.021(4) 0.028(4) 0.043(5) -0.012(3) 0.007(3) -0.004(3) C14 0.022(4) 0.032(4) 0.046(5) -0.011(3) 0.006(3) 0.004(3) C15 0.027(3) 0.029(4) 0.052(5) -0.009(4) -0.005(4) 0.005(3) C16 0.023(3) 0.013(3) 0.042(5) -0.002(3) 0.003(3) 0.002(2) C17 0.022(4) 0.016(3) 0.051(5) -0.008(3) -0.011(3) 0.001(3) C18 0.038(4) 0.030(4) 0.049(5) -0.009(4) -0.010(4) 0.010(4) C19 0.050(5) 0.032(4) 0.040(4) 0.007(4) -0.020(4) 0.006(4) C20 0.044(5) 0.039(4) 0.030(4) -0.006(3) -0.003(4) 0.003(4) C21 0.030(4) 0.025(3) 0.036(4) -0.001(3) -0.005(4) -0.003(3) C22 0.022(4) 0.018(3) 0.029(4) -0.001(3) -0.009(3) 0.002(3) C23 0.012(3) 0.025(3) 0.045(4) -0.011(4) 0.007(3) 0.003(3) C24 0.020(4) 0.020(3) 0.039(4) 0.001(3) 0.005(3) 0.002(3) C25 0.026(4) 0.018(3) 0.056(5) -0.013(3) 0.000(3) -0.001(3) C26 0.030(4) 0.040(4) 0.039(4) -0.009(4) -0.005(4) 0.002(3) C27 0.028(4) 0.033(4) 0.034(4) -0.007(3) -0.001(3) 0.000(3) C28 0.016(3) 0.023(4) 0.034(4) -0.004(3) -0.004(3) -0.001(3) C29 0.019(3) 0.024(3) 0.026(3) -0.005(3) 0.005(2) 0.002(3) C30 0.020(3) 0.023(3) 0.034(4) 0.001(3) -0.003(3) -0.001(3) C31 0.030(4) 0.027(4) 0.035(4) 0.004(3) 0.011(3) 0.001(3) C32 0.028(4) 0.021(3) 0.023(4) 0.008(3) 0.000(3) 0.003(3) C33 0.024(4) 0.029(4) 0.027(4) 0.007(3) -0.001(3) -0.002(3) C34 0.031(4) 0.034(4) 0.034(4) 0.001(4) 0.005(3) 0.011(4) C35 0.050(5) 0.026(4) 0.022(4) -0.002(3) 0.004(4) 0.016(3) C36 0.043(5) 0.018(3) 0.038(4) -0.003(3) -0.005(4) 0.004(3) C37 0.031(4) 0.023(4) 0.032(4) 0.006(3) 0.001(3) -0.006(3) C38 0.090(8) 0.053(6) 0.043(5) 0.002(4) -0.004(5) -0.020(6) O2 0.048(3) 0.046(3) 0.064(4) -0.016(3) -0.024(3) -0.009(3) C39 0.18(3) 0.12(2) 0.042(14) 0.015(14) 0.007(18) -0.04(2) O3 0.131(19) 0.097(15) 0.123(16) -0.030(12) -0.072(15) 0.031(13) C40 0.060(7) 0.055(6) 0.174(13) -0.013(9) -0.029(10) 0.013(5) O4 0.100(7) 0.151(9) 0.081(6) -0.029(6) -0.008(6) 0.071(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C11 2.001(6) . ? Ir1 C22 2.006(6) . ? Ir1 N2 2.040(6) . ? Ir1 N1 2.041(5) . ? Ir1 N3 2.132(6) . ? Ir1 O1 2.145(4) . ? O1 C23 1.323(8) . ? N1 C1 1.347(9) . ? N1 C5 1.354(8) . ? N2 C16 1.356(9) . ? N2 C12 1.365(9) . ? N3 C29 1.274(8) . ? N3 C30 1.512(8) . ? C1 C2 1.376(10) . ? C1 H1 0.9500 . ? C2 C3 1.383(10) . ? C2 H2 0.9500 . ? C3 C4 1.402(10) . ? C3 H3 0.9500 . ? C4 C5 1.389(9) . ? C4 H4 0.9500 . ? C5 C6 1.455(9) . ? C6 C7 1.392(9) . ? C6 C11 1.416(9) . ? C7 C8 1.390(11) . ? C7 H7 0.9500 . ? C8 C9 1.375(11) . ? C8 H8 0.9500 . ? C9 C10 1.390(10) . ? C9 H9 0.9500 . ? C10 C11 1.400(10) . ? C10 H10 0.9500 . ? C12 C13 1.381(10) . ? C12 H12 0.9500 . ? C13 C14 1.365(10) . ? C13 H13 0.9500 . ? C14 C15 1.391(11) . ? C14 H14 0.9500 . ? C15 C16 1.395(9) . ? C15 H15 0.9500 . ? C16 C17 1.450(10) . ? C17 C18 1.394(10) . ? C17 C22 1.427(9) . ? C18 C19 1.380(11) . ? C18 H18 0.9500 . ? C19 C20 1.396(11) . ? C19 H19 0.9500 . ? C20 C21 1.394(10) . ? C20 H20 0.9500 . ? C21 C22 1.387(9) . ? C21 H21 0.9500 . ? C23 C28 1.410(10) . ? C23 C24 1.419(10) . ? C24 C25 1.359(10) . ? C24 H24 0.9500 . ? C25 C26 1.390(11) . ? C25 H25 0.9500 . ? C26 C27 1.376(11) . ? C26 H26 0.9500 . ? C27 C28 1.418(9) . ? C27 H27 0.9500 . ? C28 C29 1.465(10) . ? C29 H29 0.9500 . ? C30 C32 1.522(9) . ? C30 C31 1.524(9) . ? C30 H30 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C33 1.384(10) . ? C32 C37 1.387(9) . ? C33 C34 1.396(10) . ? C33 H33 0.9500 . ? C34 C35 1.366(11) . ? C34 H34 0.9500 . ? C35 C36 1.374(11) . ? C35 H35 0.9500 . ? C36 C37 1.382(10) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 O2 1.439(10) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? O2 H2A 0.8400 . ? C39 O3 1.39(3) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? O3 H3A 0.8400 . ? C40 O4 1.385(14) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? O4 H4A 0.8400 . ? 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 C11 Ir1 C22 86.1(3) . . ? C11 Ir1 N2 94.6(3) . . ? C22 Ir1 N2 80.6(3) . . ? C11 Ir1 N1 80.2(2) . . ? C22 Ir1 N1 94.0(2) . . ? N2 Ir1 N1 172.9(2) . . ? C11 Ir1 N3 97.9(2) . . ? C22 Ir1 N3 173.5(2) . . ? N2 Ir1 N3 93.9(2) . . ? N1 Ir1 N3 91.7(2) . . ? C11 Ir1 O1 171.5(2) . . ? C22 Ir1 O1 88.0(2) . . ? N2 Ir1 O1 90.39(19) . . ? N1 Ir1 O1 94.15(19) . . ? N3 Ir1 O1 88.50(19) . . ? C23 O1 Ir1 127.2(4) . . ? C1 N1 C5 119.8(6) . . ? C1 N1 Ir1 124.2(4) . . ? C5 N1 Ir1 116.0(4) . . ? C16 N2 C12 119.3(6) . . ? C16 N2 Ir1 116.1(4) . . ? C12 N2 Ir1 124.6(5) . . ? C29 N3 C30 116.4(6) . . ? C29 N3 Ir1 125.7(5) . . ? C30 N3 Ir1 117.7(4) . . ? N1 C1 C2 122.2(6) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C1 C2 C3 118.9(7) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 119.0(7) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 119.3(6) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N1 C5 C4 120.5(6) . . ? N1 C5 C6 114.1(6) . . ? C4 C5 C6 125.4(6) . . ? C7 C6 C11 121.1(7) . . ? C7 C6 C5 123.9(6) . . ? C11 C6 C5 114.9(6) . . ? C8 C7 C6 119.9(7) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 119.5(7) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 121.4(7) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C9 C10 C11 120.4(7) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 117.7(6) . . ? C10 C11 Ir1 127.9(5) . . ? C6 C11 Ir1 114.4(5) . . ? N2 C12 C13 121.9(7) . . ? N2 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C14 C13 C12 119.1(7) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 119.8(7) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 119.7(7) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? N2 C16 C15 120.2(7) . . ? N2 C16 C17 114.1(6) . . ? C15 C16 C17 125.7(7) . . ? C18 C17 C22 120.9(7) . . ? C18 C17 C16 123.5(7) . . ? C22 C17 C16 115.5(6) . . ? C19 C18 C17 120.1(7) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.1(7) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C21 C20 C19 119.7(7) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 C20 121.9(7) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C21 C22 C17 117.3(6) . . ? C21 C22 Ir1 129.1(5) . . ? C17 C22 Ir1 113.6(5) . . ? O1 C23 C28 124.5(6) . . ? O1 C23 C24 118.1(7) . . ? C28 C23 C24 117.4(6) . . ? C25 C24 C23 122.4(7) . . ? C25 C24 H24 118.8 . . ? C23 C24 H24 118.8 . . ? C24 C25 C26 120.6(7) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C27 C26 C25 118.7(7) . . ? C27 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? C26 C27 C28 122.2(7) . . ? C26 C27 H27 118.9 . . ? C28 C27 H27 118.9 . . ? C23 C28 C27 118.7(6) . . ? C23 C28 C29 126.4(6) . . ? C27 C28 C29 115.0(6) . . ? N3 C29 C28 127.7(6) . . ? N3 C29 H29 116.1 . . ? C28 C29 H29 116.1 . . ? N3 C30 C32 112.0(5) . . ? N3 C30 C31 115.4(5) . . ? C32 C30 C31 109.6(5) . . ? N3 C30 H30 106.4 . . ? C32 C30 H30 106.4 . . ? C31 C30 H30 106.4 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C33 C32 C37 119.6(7) . . ? C33 C32 C30 122.2(6) . . ? C37 C32 C30 117.9(6) . . ? C32 C33 C34 119.8(7) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C35 C34 C33 120.0(7) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C36 120.3(7) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C35 C36 C37 120.4(7) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C36 C37 C32 119.8(7) . . ? C36 C37 H37 120.1 . . ? C32 C37 H37 120.1 . . ? O2 C38 H38A 109.5 . . ? O2 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O2 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C38 O2 H2A 109.5 . . ? O3 C39 H39A 109.5 . . ? O3 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O3 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C39 O3 H3A 109.5 . . ? O4 C40 H40A 109.5 . . ? O4 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O4 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C40 O4 H4A 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 C22 Ir1 O1 C23 -172.6(5) . . . . ? N2 Ir1 O1 C23 -92.0(5) . . . . ? N1 Ir1 O1 C23 93.5(5) . . . . ? N3 Ir1 O1 C23 1.8(5) . . . . ? C11 Ir1 N1 C1 176.1(6) . . . . ? C22 Ir1 N1 C1 -98.6(6) . . . . ? N3 Ir1 N1 C1 78.3(6) . . . . ? O1 Ir1 N1 C1 -10.3(6) . . . . ? C11 Ir1 N1 C5 -5.6(5) . . . . ? C22 Ir1 N1 C5 79.7(5) . . . . ? N3 Ir1 N1 C5 -103.4(5) . . . . ? O1 Ir1 N1 C5 168.0(5) . . . . ? C11 Ir1 N2 C16 82.4(5) . . . . ? C22 Ir1 N2 C16 -2.9(5) . . . . ? N3 Ir1 N2 C16 -179.3(4) . . . . ? O1 Ir1 N2 C16 -90.8(5) . . . . ? C11 Ir1 N2 C12 -97.3(5) . . . . ? C22 Ir1 N2 C12 177.4(6) . . . . ? N3 Ir1 N2 C12 1.0(5) . . . . ? O1 Ir1 N2 C12 89.5(5) . . . . ? C11 Ir1 N3 C29 -175.9(5) . . . . ? N2 Ir1 N3 C29 88.9(5) . . . . ? N1 Ir1 N3 C29 -95.5(5) . . . . ? O1 Ir1 N3 C29 -1.4(5) . . . . ? C11 Ir1 N3 C30 8.8(5) . . . . ? N2 Ir1 N3 C30 -86.4(4) . . . . ? N1 Ir1 N3 C30 89.2(4) . . . . ? O1 Ir1 N3 C30 -176.7(4) . . . . ? C5 N1 C1 C2 0.5(10) . . . . ? Ir1 N1 C1 C2 178.7(5) . . . . ? N1 C1 C2 C3 -2.7(11) . . . . ? C1 C2 C3 C4 1.6(11) . . . . ? C2 C3 C4 C5 1.5(11) . . . . ? C1 N1 C5 C4 2.7(10) . . . . ? Ir1 N1 C5 C4 -175.6(5) . . . . ? C1 N1 C5 C6 -176.4(6) . . . . ? Ir1 N1 C5 C6 5.3(7) . . . . ? C3 C4 C5 N1 -3.7(10) . . . . ? C3 C4 C5 C6 175.3(7) . . . . ? N1 C5 C6 C7 176.5(6) . . . . ? C4 C5 C6 C7 -2.6(11) . . . . ? N1 C5 C6 C11 -1.2(8) . . . . ? C4 C5 C6 C11 179.7(6) . . . . ? C11 C6 C7 C8 -1.0(10) . . . . ? C5 C6 C7 C8 -178.6(6) . . . . ? C6 C7 C8 C9 0.8(11) . . . . ? C7 C8 C9 C10 -1.0(12) . . . . ? C8 C9 C10 C11 1.3(12) . . . . ? C9 C10 C11 C6 -1.4(10) . . . . ? C9 C10 C11 Ir1 -178.5(6) . . . . ? C7 C6 C11 C10 1.2(10) . . . . ? C5 C6 C11 C10 179.0(6) . . . . ? C7 C6 C11 Ir1 178.7(5) . . . . ? C5 C6 C11 Ir1 -3.5(7) . . . . ? C22 Ir1 C11 C10 87.2(6) . . . . ? N2 Ir1 C11 C10 6.9(6) . . . . ? N1 Ir1 C11 C10 -178.0(6) . . . . ? N3 Ir1 C11 C10 -87.6(6) . . . . ? C22 Ir1 C11 C6 -90.0(5) . . . . ? N2 Ir1 C11 C6 -170.2(5) . . . . ? N1 Ir1 C11 C6 4.8(5) . . . . ? N3 Ir1 C11 C6 95.2(5) . . . . ? C16 N2 C12 C13 -1.8(10) . . . . ? Ir1 N2 C12 C13 177.8(5) . . . . ? N2 C12 C13 C14 1.6(11) . . . . ? C12 C13 C14 C15 0.0(11) . . . . ? C13 C14 C15 C16 -1.4(10) . . . . ? C12 N2 C16 C15 0.4(9) . . . . ? Ir1 N2 C16 C15 -179.3(5) . . . . ? C12 N2 C16 C17 -177.8(6) . . . . ? Ir1 N2 C16 C17 2.5(7) . . . . ? C14 C15 C16 N2 1.2(10) . . . . ? C14 C15 C16 C17 179.2(6) . . . . ? N2 C16 C17 C18 177.0(6) . . . . ? C15 C16 C17 C18 -1.1(11) . . . . ? N2 C16 C17 C22 -0.2(8) . . . . ? C15 C16 C17 C22 -178.3(6) . . . . ? C22 C17 C18 C19 -2.2(11) . . . . ? C16 C17 C18 C19 -179.2(7) . . . . ? C17 C18 C19 C20 3.1(12) . . . . ? C18 C19 C20 C21 -3.0(12) . . . . ? C19 C20 C21 C22 2.1(11) . . . . ? C20 C21 C22 C17 -1.2(10) . . . . ? C20 C21 C22 Ir1 179.6(5) . . . . ? C18 C17 C22 C21 1.2(10) . . . . ? C16 C17 C22 C21 178.5(6) . . . . ? C18 C17 C22 Ir1 -179.4(5) . . . . ? C16 C17 C22 Ir1 -2.2(7) . . . . ? C11 Ir1 C22 C21 86.5(6) . . . . ? N2 Ir1 C22 C21 -178.1(6) . . . . ? N1 Ir1 C22 C21 6.6(6) . . . . ? O1 Ir1 C22 C21 -87.4(6) . . . . ? C11 Ir1 C22 C17 -92.7(5) . . . . ? N2 Ir1 C22 C17 2.6(5) . . . . ? N1 Ir1 C22 C17 -172.6(5) . . . . ? O1 Ir1 C22 C17 93.4(5) . . . . ? Ir1 O1 C23 C28 -1.0(9) . . . . ? Ir1 O1 C23 C24 177.8(4) . . . . ? O1 C23 C24 C25 -176.9(6) . . . . ? C28 C23 C24 C25 2.0(10) . . . . ? C23 C24 C25 C26 0.0(11) . . . . ? C24 C25 C26 C27 -1.7(11) . . . . ? C25 C26 C27 C28 1.5(11) . . . . ? O1 C23 C28 C27 176.6(6) . . . . ? C24 C23 C28 C27 -2.2(9) . . . . ? O1 C23 C28 C29 -1.1(11) . . . . ? C24 C23 C28 C29 -180.0(6) . . . . ? C26 C27 C28 C23 0.5(10) . . . . ? C26 C27 C28 C29 178.5(6) . . . . ? C30 N3 C29 C28 175.5(6) . . . . ? Ir1 N3 C29 C28 0.1(9) . . . . ? C23 C28 C29 N3 1.6(11) . . . . ? C27 C28 C29 N3 -176.2(6) . . . . ? C29 N3 C30 C32 107.9(6) . . . . ? Ir1 N3 C30 C32 -76.4(6) . . . . ? C29 N3 C30 C31 -18.5(8) . . . . ? Ir1 N3 C30 C31 157.3(5) . . . . ? N3 C30 C32 C33 -37.7(9) . . . . ? C31 C30 C32 C33 91.7(8) . . . . ? N3 C30 C32 C37 147.7(6) . . . . ? C31 C30 C32 C37 -82.8(7) . . . . ? C37 C32 C33 C34 -2.2(10) . . . . ? C30 C32 C33 C34 -176.7(6) . . . . ? C32 C33 C34 C35 2.8(11) . . . . ? C33 C34 C35 C36 -2.5(11) . . . . ? C34 C35 C36 C37 1.7(11) . . . . ? C35 C36 C37 C32 -1.1(11) . . . . ? C33 C32 C37 C36 1.3(11) . . . . ? C30 C32 C37 C36 176.1(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.377 _refine_diff_density_min -1.955 _refine_diff_density_rms 0.132 #===END _database_code_depnum_ccdc_archive 'CCDC 922566'