# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_pkb247 _database_code_depnum_ccdc_archive 'CCDC 910293' #TrackingRef 'PKB247revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H14 N4 O4' _chemical_formula_sum 'C22 H14 N4 O4' _chemical_formula_weight 398.37 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.196(8) _cell_length_b 7.0193(16) _cell_length_c 13.309(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.79(3) _cell_angle_gamma 90.00 _cell_volume 1806.3(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3663 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 61.23 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9795 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; Crystal was weakly diffracting. The R factor is high due to weak data and slight twinning. ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17964 _diffrn_reflns_av_R_equivalents 0.1149 _diffrn_reflns_av_unetI/netI 0.0558 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3189 _reflns_number_gt 2573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _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^)+(0.1259P)^2^+10.8580P] 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 SHELXL _refine_ls_extinction_coef 0.019(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3189 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1260 _refine_ls_R_factor_gt 0.1076 _refine_ls_wR_factor_ref 0.3266 _refine_ls_wR_factor_gt 0.3112 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _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 N1 N 0.0704(2) 0.2979(7) 0.2383(4) 0.0361(12) Uani 1 1 d . . . N2 N 0.2397(2) 0.4881(7) 0.3565(4) 0.0325(11) Uani 1 1 d . . . C1 C 0.0156(3) 0.2382(10) 0.2667(5) 0.0418(15) Uani 1 1 d . . . H1A H -0.0216 0.1808 0.2150 0.050 Uiso 1 1 calc R . . C2 C 0.0105(3) 0.2557(10) 0.3676(5) 0.0442(16) Uani 1 1 d . . . H2A H -0.0290 0.2087 0.3849 0.053 Uiso 1 1 calc R . . C3 C 0.0635(3) 0.3424(10) 0.4427(5) 0.0416(16) Uani 1 1 d . . . H3A H 0.0605 0.3598 0.5121 0.050 Uiso 1 1 calc R . . C4 C 0.1207(3) 0.4034(9) 0.4160(5) 0.0337(13) Uani 1 1 d . . . H4A H 0.1586 0.4599 0.4670 0.040 Uiso 1 1 calc R . . C5 C 0.1224(3) 0.3808(8) 0.3125(4) 0.0293(12) Uani 1 1 d . . . C6 C 0.1824(3) 0.4424(8) 0.2804(5) 0.0302(13) Uani 1 1 d . . . C7 C 0.1793(3) 0.4510(8) 0.1751(5) 0.0310(13) Uani 1 1 d . . . H7A H 0.1377 0.4197 0.1227 0.037 Uiso 1 1 calc R . . C8 C 0.2377(3) 0.5058(9) 0.1468(5) 0.0333(13) Uani 1 1 d . . . C9 C 0.2973(3) 0.5497(9) 0.2262(5) 0.0343(14) Uani 1 1 d . . . H9A H 0.3384 0.5845 0.2096 0.041 Uiso 1 1 calc R . . C10 C 0.2965(3) 0.5425(8) 0.3316(5) 0.0297(13) Uani 1 1 d . . . C11 C 0.3576(3) 0.5903(9) 0.4196(5) 0.0315(13) Uani 1 1 d . . . C12 C 0.3582(3) 0.5367(9) 0.5212(5) 0.0362(14) Uani 1 1 d . . . H12A H 0.3195 0.4710 0.5313 0.043 Uiso 1 1 calc R . . C13 C 0.4136(3) 0.5771(10) 0.6067(5) 0.0392(15) Uani 1 1 d . . . H13A H 0.4144 0.5360 0.6750 0.047 Uiso 1 1 calc R . . C14 C 0.4681(3) 0.6793(9) 0.5903(5) 0.0373(14) Uani 1 1 d . . . C15 C 0.4693(3) 0.7367(10) 0.4921(5) 0.0393(15) Uani 1 1 d . . . H15A H 0.5078 0.8052 0.4831 0.047 Uiso 1 1 calc R . . C16 C 0.4137(3) 0.6936(9) 0.4065(5) 0.0372(14) Uani 1 1 d . . . H16A H 0.4137 0.7344 0.3384 0.045 Uiso 1 1 calc R . . N3 N 0.5280(3) 0.7166(9) 0.6810(5) 0.0465(15) Uani 1 1 d . . . O1 O 0.5304(3) 0.6457(9) 0.7665(4) 0.0618(16) Uani 1 1 d . . . O2 O 0.5736(3) 0.8209(9) 0.6685(4) 0.0616(16) Uani 1 1 d . . . C17 C 0.2345(3) 0.5154(8) 0.0342(5) 0.0339(13) Uani 1 1 d . . . C18 C 0.1745(3) 0.5795(9) -0.0388(5) 0.0369(14) Uani 1 1 d . . . H18A H 0.1365 0.6214 -0.0158 0.044 Uiso 1 1 calc R . . C19 C 0.1698(3) 0.5826(9) -0.1452(5) 0.0373(14) Uani 1 1 d . . . H19A H 0.1287 0.6250 -0.1954 0.045 Uiso 1 1 calc R . . C20 C 0.2251(3) 0.5236(8) -0.1759(5) 0.0360(14) Uani 1 1 d . . . C21 C 0.2857(3) 0.4616(9) -0.1062(5) 0.0390(15) Uani 1 1 d . . . H21A H 0.3235 0.4208 -0.1301 0.047 Uiso 1 1 calc R . . C22 C 0.2904(3) 0.4602(9) 0.0010(5) 0.0382(14) Uani 1 1 d . . . H22A H 0.3321 0.4211 0.0509 0.046 Uiso 1 1 calc R . . N4 N 0.2196(3) 0.5227(8) -0.2890(5) 0.0464(15) Uani 1 1 d . . . O3 O 0.2693(3) 0.4726(9) -0.3154(5) 0.0670(17) Uani 1 1 d . . . O4 O 0.1650(3) 0.5765(9) -0.3483(4) 0.0631(15) 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 N1 0.033(3) 0.036(3) 0.038(3) -0.005(2) 0.008(2) -0.002(2) N2 0.034(3) 0.031(3) 0.032(3) 0.003(2) 0.009(2) 0.003(2) C1 0.035(3) 0.042(4) 0.046(4) -0.008(3) 0.008(3) -0.008(3) C2 0.038(3) 0.047(4) 0.050(4) 0.001(3) 0.015(3) -0.007(3) C3 0.038(3) 0.052(4) 0.040(4) 0.001(3) 0.021(3) 0.000(3) C4 0.032(3) 0.037(3) 0.031(3) -0.003(3) 0.008(2) -0.003(2) C5 0.033(3) 0.026(3) 0.031(3) 0.002(2) 0.011(2) 0.005(2) C6 0.030(3) 0.024(3) 0.035(3) -0.001(2) 0.006(2) 0.002(2) C7 0.027(3) 0.033(3) 0.032(3) -0.001(2) 0.008(2) 0.001(2) C8 0.034(3) 0.031(3) 0.034(3) -0.002(2) 0.010(3) 0.001(2) C9 0.029(3) 0.038(3) 0.037(3) 0.000(3) 0.011(2) -0.002(2) C10 0.025(3) 0.027(3) 0.036(3) 0.001(2) 0.007(2) 0.002(2) C11 0.028(3) 0.031(3) 0.038(3) 0.001(2) 0.015(2) 0.002(2) C12 0.032(3) 0.042(3) 0.036(3) -0.002(3) 0.012(3) -0.003(3) C13 0.040(3) 0.043(4) 0.038(3) 0.001(3) 0.016(3) 0.002(3) C14 0.034(3) 0.040(3) 0.036(3) -0.009(3) 0.007(3) 0.002(3) C15 0.032(3) 0.042(3) 0.046(4) -0.003(3) 0.015(3) -0.006(3) C16 0.035(3) 0.043(4) 0.037(3) 0.000(3) 0.015(3) -0.002(3) N3 0.037(3) 0.055(4) 0.047(4) -0.013(3) 0.013(3) -0.004(3) O1 0.054(3) 0.087(4) 0.038(3) 0.000(3) 0.003(2) -0.012(3) O2 0.043(3) 0.086(4) 0.058(3) -0.022(3) 0.018(2) -0.025(3) C17 0.038(3) 0.028(3) 0.038(3) -0.003(2) 0.015(3) -0.007(2) C18 0.037(3) 0.040(3) 0.036(3) -0.006(3) 0.014(3) -0.002(3) C19 0.042(3) 0.032(3) 0.039(3) -0.003(3) 0.014(3) -0.006(3) C20 0.053(4) 0.025(3) 0.036(3) -0.005(2) 0.023(3) -0.012(3) C21 0.045(3) 0.030(3) 0.050(4) -0.008(3) 0.026(3) -0.006(3) C22 0.041(3) 0.033(3) 0.045(4) -0.003(3) 0.019(3) 0.000(3) N4 0.066(4) 0.036(3) 0.044(3) -0.006(3) 0.028(3) -0.012(3) O3 0.078(4) 0.079(4) 0.059(3) -0.006(3) 0.044(3) -0.008(3) O4 0.076(4) 0.071(4) 0.042(3) 0.000(3) 0.016(3) -0.007(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 N1 C1 1.335(8) . ? N1 C5 1.348(7) . ? N2 C10 1.338(7) . ? N2 C6 1.339(7) . ? C1 C2 1.382(9) . ? C1 H1A 0.9500 . ? C2 C3 1.378(9) . ? C2 H2A 0.9500 . ? C3 C4 1.373(8) . ? C3 H3A 0.9500 . ? C4 C5 1.396(8) . ? C4 H4A 0.9500 . ? C5 C6 1.461(8) . ? C6 C7 1.387(8) . ? C7 C8 1.391(8) . ? C7 H7A 0.9500 . ? C8 C9 1.387(8) . ? C8 C17 1.484(8) . ? C9 C10 1.407(8) . ? C9 H9A 0.9500 . ? C10 C11 1.474(8) . ? C11 C16 1.398(8) . ? C11 C12 1.400(8) . ? C12 C13 1.375(9) . ? C12 H12A 0.9500 . ? C13 C14 1.382(9) . ? C13 H13A 0.9500 . ? C14 C15 1.375(9) . ? C14 N3 1.464(8) . ? C15 C16 1.382(9) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? N3 O2 1.226(8) . ? N3 O1 1.228(8) . ? C17 C22 1.380(8) . ? C17 C18 1.392(9) . ? C18 C19 1.392(8) . ? C18 H18A 0.9500 . ? C19 C20 1.361(9) . ? C19 H19A 0.9500 . ? C20 C21 1.376(9) . ? C20 N4 1.477(8) . ? C21 C22 1.403(9) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? N4 O3 1.207(8) . ? N4 O4 1.217(8) . ? 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 C1 N1 C5 117.5(5) . . ? C10 N2 C6 119.8(5) . . ? N1 C1 C2 123.2(6) . . ? N1 C1 H1A 118.4 . . ? C2 C1 H1A 118.4 . . ? C3 C2 C1 119.0(6) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C4 C3 C2 119.0(6) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 118.8(6) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? N1 C5 C4 122.4(5) . . ? N1 C5 C6 116.8(5) . . ? C4 C5 C6 120.8(5) . . ? N2 C6 C7 122.0(5) . . ? N2 C6 C5 117.3(5) . . ? C7 C6 C5 120.7(5) . . ? C6 C7 C8 119.5(5) . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C9 C8 C7 118.1(5) . . ? C9 C8 C17 122.3(5) . . ? C7 C8 C17 119.6(5) . . ? C8 C9 C10 119.6(5) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? N2 C10 C9 121.0(5) . . ? N2 C10 C11 116.6(5) . . ? C9 C10 C11 122.3(5) . . ? C16 C11 C12 118.6(6) . . ? C16 C11 C10 122.8(5) . . ? C12 C11 C10 118.6(5) . . ? C13 C12 C11 121.4(6) . . ? C13 C12 H12A 119.3 . . ? C11 C12 H12A 119.3 . . ? C12 C13 C14 118.1(6) . . ? C12 C13 H13A 120.9 . . ? C14 C13 H13A 120.9 . . ? C15 C14 C13 122.3(6) . . ? C15 C14 N3 119.7(6) . . ? C13 C14 N3 117.9(6) . . ? C14 C15 C16 119.1(6) . . ? C14 C15 H15A 120.4 . . ? C16 C15 H15A 120.4 . . ? C15 C16 C11 120.4(6) . . ? C15 C16 H16A 119.8 . . ? C11 C16 H16A 119.8 . . ? O2 N3 O1 122.5(6) . . ? O2 N3 C14 117.9(6) . . ? O1 N3 C14 119.6(6) . . ? C22 C17 C18 119.7(6) . . ? C22 C17 C8 120.7(6) . . ? C18 C17 C8 119.6(5) . . ? C17 C18 C19 120.3(6) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C20 C19 C18 118.7(6) . . ? C20 C19 H19A 120.7 . . ? C18 C19 H19A 120.7 . . ? C19 C20 C21 122.9(6) . . ? C19 C20 N4 118.7(6) . . ? C21 C20 N4 118.4(6) . . ? C20 C21 C22 118.2(6) . . ? C20 C21 H21A 120.9 . . ? C22 C21 H21A 120.9 . . ? C17 C22 C21 120.2(6) . . ? C17 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? O3 N4 O4 125.1(6) . . ? O3 N4 C20 118.3(6) . . ? O4 N4 C20 116.6(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.404 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.086 data_pk236 _database_code_depnum_ccdc_archive 'CCDC 910295' #TrackingRef 'pk236_monoclinic.cif' _audit_creation_date 11-10-14 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'pka236_123k_0ma in P2(1)/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.0887(7) _cell_length_b 17.9889(8) _cell_length_c 10.9843(8) _cell_angle_alpha 90 _cell_angle_beta 108.615(3) _cell_angle_gamma 90 _cell_volume 2451.0(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C28 H28 N2 O6 # Dc = 1.32 Fooo = 1032.00 Mu = 0.94 M = 488.54 # Found Formula = C28 H28 N2 O6 # Dc = 1.32 FOOO = 1032.00 Mu = 0.94 M = 488.54 _chemical_formula_sum 'C28 H28 N2 O6' _chemical_formula_moiety 'C28 H28 N2 O6' _chemical_compound_source ? _chemical_formula_weight 488.54 _cell_measurement_reflns_used 4138 _cell_measurement_theta_min 4 _cell_measurement_theta_max 27 _cell_measurement_temperature 123 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_max 0.270 _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.094 # Sheldrick geometric approximatio 0.99 0.99 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 27283 _reflns_number_total 5624 _diffrn_reflns_av_R_equivalents 0.054 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 5624 # Theoretical number of reflections is about 11263 _diffrn_reflns_theta_min 1.642 _diffrn_reflns_theta_max 27.503 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.503 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -16 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 23 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.21 _refine_diff_density_max 0.23 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 3375 _refine_ls_number_restraints 0 _refine_ls_number_parameters 325 _oxford_refine_ls_R_factor_ref 0.0397 _refine_ls_wR_factor_ref 0.0398 _refine_ls_goodness_of_fit_ref 1.1104 _refine_ls_shift/su_max 0.0005055 _refine_ls_shift/su_mean 0.0000460 # The values computed from all data _oxford_reflns_number_all 5608 _refine_ls_R_factor_all 0.0842 _refine_ls_wR_factor_all 0.0879 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3375 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_gt 0.0398 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.227 0.225 0.992E-01 ; # Insert your own references if required - in alphabetical order loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.42697(12) 0.64351(8) 0.45301(14) 0.0247 1.0000 Uani . . . . . . N2 N 0.14163(13) 0.68067(9) 0.36314(15) 0.0309 1.0000 Uani . . . . . . C1 C 0.50603(14) 0.61158(10) 0.54900(16) 0.0232 1.0000 Uani . . . . . . C2 C 0.48469(14) 0.57783(10) 0.65286(16) 0.0234 1.0000 Uani . . . . . . C3 C 0.37925(14) 0.57253(10) 0.65476(16) 0.0224 1.0000 Uani . . . . . . C4 C 0.29834(14) 0.60437(10) 0.55397(16) 0.0224 1.0000 Uani . . . . . . C5 C 0.32536(14) 0.64073(10) 0.45775(16) 0.0226 1.0000 Uani . . . . . . C6 C 0.24046(15) 0.67814(10) 0.35195(17) 0.0263 1.0000 Uani . . . . . . C7 C 0.26239(17) 0.70856(11) 0.24718(17) 0.0330 1.0000 Uani . . . . . . C8 C 0.18007(19) 0.74074(12) 0.1508(2) 0.0420 1.0000 Uani . . . . . . C9 C 0.07787(19) 0.74305(11) 0.16052(19) 0.0410 1.0000 Uani . . . . . . C10 C 0.06221(18) 0.71277(11) 0.26805(19) 0.0372 1.0000 Uani . . . . . . C11 C 0.61689(14) 0.61347(10) 0.53939(16) 0.0222 1.0000 Uani . . . . . . C12 C 0.69701(14) 0.56761(10) 0.61687(16) 0.0235 1.0000 Uani . . . . . . C13 C 0.79978(14) 0.56842(10) 0.60620(16) 0.0227 1.0000 Uani . . . . . . C14 C 0.82328(13) 0.61501(10) 0.51732(16) 0.0220 1.0000 Uani . . . . . . C15 C 0.74295(14) 0.66167(10) 0.44046(16) 0.0228 1.0000 Uani . . . . . . C16 C 0.64012(14) 0.66124(10) 0.45119(16) 0.0224 1.0000 Uani . . . . . . C17 C 0.87096(16) 0.49027(11) 0.78907(18) 0.0292 1.0000 Uani . . . . . . C18 C 0.93196(16) 0.57230(12) 0.40065(18) 0.0327 1.0000 Uani . . . . . . C19 C 0.69648(16) 0.75354(11) 0.27397(18) 0.0329 1.0000 Uani . . . . . . C20 C 0.35218(13) 0.53292(10) 0.75936(15) 0.0215 1.0000 Uani . . . . . . C21 C 0.26406(13) 0.55660(10) 0.79431(16) 0.0214 1.0000 Uani . . . . . . C22 C 0.23528(14) 0.51782(10) 0.88780(16) 0.0224 1.0000 Uani . . . . . . C23 C 0.29344(14) 0.45518(10) 0.94533(16) 0.0224 1.0000 Uani . . . . . . C24 C 0.38292(14) 0.43279(10) 0.91234(16) 0.0229 1.0000 Uani . . . . . . C25 C 0.41237(14) 0.47173(10) 0.81924(16) 0.0226 1.0000 Uani . . . . . . C26 C 0.09716(15) 0.60492(11) 0.88151(19) 0.0304 1.0000 Uani . . . . . . C27 C 0.17649(16) 0.36553(11) 0.97857(19) 0.0323 1.0000 Uani . . . . . . C28 C 0.53394(15) 0.35098(11) 0.9547(2) 0.0331 1.0000 Uani . . . . . . O1 O 0.88272(10) 0.52447(7) 0.67696(12) 0.0291 1.0000 Uani . . . . . . O2 O 0.92534(10) 0.61561(7) 0.50709(11) 0.0269 1.0000 Uani . . . . . . O3 O 0.77544(10) 0.70610(7) 0.35855(12) 0.0280 1.0000 Uani . . . . . . O4 O 0.15106(10) 0.53682(7) 0.92972(12) 0.0281 1.0000 Uani . . . . . . O5 O 0.26358(10) 0.41570(7) 1.03656(11) 0.0275 1.0000 Uani . . . . . . O6 O 0.43465(10) 0.37076(7) 0.97421(12) 0.0290 1.0000 Uani . . . . . . H21 H 0.5415 0.5594 0.7230 0.0265 1.0000 Uiso R . . . . . H41 H 0.2276 0.6014 0.5511 0.0264 1.0000 Uiso R . . . . . H71 H 0.3336 0.7067 0.2450 0.0400 1.0000 Uiso R . . . . . H81 H 0.1940 0.7602 0.0764 0.0501 1.0000 Uiso R . . . . . H91 H 0.0204 0.7655 0.0966 0.0476 1.0000 Uiso R . . . . . H101 H -0.0076 0.7155 0.2765 0.0422 1.0000 Uiso R . . . . . H121 H 0.6811 0.5353 0.6765 0.0270 1.0000 Uiso R . . . . . H161 H 0.5857 0.6926 0.3995 0.0262 1.0000 Uiso R . . . . . H172 H 0.9396 0.4670 0.8343 0.0430 1.0000 Uiso R . . . . . H171 H 0.8526 0.5265 0.8434 0.0419 1.0000 Uiso R . . . . . H173 H 0.8139 0.4527 0.7630 0.0422 1.0000 Uiso R . . . . . H182 H 1.0060 0.5753 0.3972 0.0475 1.0000 Uiso R . . . . . H181 H 0.8799 0.5915 0.3196 0.0474 1.0000 Uiso R . . . . . H183 H 0.9136 0.5202 0.4120 0.0478 1.0000 Uiso R . . . . . H191 H 0.7343 0.7820 0.2243 0.0476 1.0000 Uiso R . . . . . H193 H 0.6645 0.7885 0.3216 0.0472 1.0000 Uiso R . . . . . H192 H 0.6403 0.7240 0.2150 0.0474 1.0000 Uiso R . . . . . H211 H 0.2247 0.5986 0.7543 0.0242 1.0000 Uiso R . . . . . H251 H 0.4709 0.4557 0.7946 0.0264 1.0000 Uiso R . . . . . H261 H 0.0448 0.6125 0.9267 0.0437 1.0000 Uiso R . . . . . H262 H 0.1488 0.6469 0.9002 0.0440 1.0000 Uiso R . . . . . H263 H 0.0586 0.6020 0.7890 0.0444 1.0000 Uiso R . . . . . H272 H 0.1552 0.3417 1.0469 0.0481 1.0000 Uiso R . . . . . H271 H 0.1148 0.3929 0.9212 0.0477 1.0000 Uiso R . . . . . H273 H 0.2009 0.3272 0.9296 0.0474 1.0000 Uiso R . . . . . H282 H 0.5628 0.3081 1.0112 0.0492 1.0000 Uiso R . . . . . H281 H 0.5846 0.3933 0.9794 0.0488 1.0000 Uiso R . . . . . H283 H 0.5236 0.3363 0.8645 0.0485 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0254(8) 0.0267(8) 0.0227(7) -0.0013(6) 0.0086(6) -0.0008(6) N2 0.0342(9) 0.0290(8) 0.0245(8) -0.0013(7) 0.0022(7) 0.0050(7) C1 0.0234(9) 0.0232(9) 0.0227(9) -0.0030(7) 0.0070(7) -0.0027(7) C2 0.0209(9) 0.0277(9) 0.0200(8) 0.0006(7) 0.0046(7) 0.0025(7) C3 0.0238(9) 0.0235(9) 0.0201(8) -0.0030(7) 0.0071(7) -0.0009(7) C4 0.0178(8) 0.0268(9) 0.0215(8) -0.0009(7) 0.0050(6) -0.0009(7) C5 0.0255(9) 0.0222(9) 0.0189(8) -0.0031(7) 0.0057(7) -0.0013(7) C6 0.0301(10) 0.0229(9) 0.0222(9) -0.0032(7) 0.0033(7) -0.0004(8) C7 0.0366(11) 0.0322(10) 0.0256(9) 0.0012(8) 0.0035(8) -0.0069(9) C8 0.0558(14) 0.0329(11) 0.0276(10) 0.0043(9) -0.0002(9) -0.0088(10) C9 0.0513(14) 0.0256(10) 0.0295(11) 0.0004(9) -0.0103(9) 0.0026(9) C10 0.0407(12) 0.0286(11) 0.0319(10) -0.0044(9) -0.0032(9) 0.0062(9) C11 0.0236(9) 0.0233(9) 0.0205(8) -0.0044(7) 0.0084(7) -0.0021(7) C12 0.0267(9) 0.0236(9) 0.0222(8) -0.0004(7) 0.0104(7) 0.0000(7) C13 0.0249(9) 0.0223(9) 0.0209(8) -0.0035(7) 0.0072(7) 0.0009(7) C14 0.0187(8) 0.0250(9) 0.0219(8) -0.0071(7) 0.0060(7) -0.0043(7) C15 0.0261(9) 0.0222(9) 0.0209(8) -0.0035(7) 0.0087(7) -0.0060(7) C16 0.0234(9) 0.0237(9) 0.0191(8) -0.0026(7) 0.0054(7) -0.0019(7) C17 0.0295(10) 0.0310(10) 0.0281(9) 0.0045(8) 0.0107(8) 0.0038(8) C18 0.0333(10) 0.0432(12) 0.0254(9) -0.0011(9) 0.0145(8) 0.0068(9) C19 0.0348(11) 0.0341(11) 0.0251(9) 0.0062(8) 0.0027(8) -0.0063(8) C20 0.0196(8) 0.0249(9) 0.0182(8) -0.0012(7) 0.0033(6) -0.0021(7) C21 0.0208(9) 0.0210(9) 0.0199(8) 0.0021(7) 0.0031(7) 0.0012(7) C22 0.0199(9) 0.0264(9) 0.0202(8) -0.0028(7) 0.0053(7) -0.0017(7) C23 0.0232(9) 0.0245(9) 0.0174(8) 0.0002(7) 0.0034(7) -0.0036(7) C24 0.0234(9) 0.0223(9) 0.0193(8) -0.0010(7) 0.0016(7) 0.0008(7) C25 0.0192(8) 0.0267(9) 0.0214(8) -0.0035(7) 0.0058(7) 0.0002(7) C26 0.0285(10) 0.0304(10) 0.0355(10) 0.0046(9) 0.0148(8) 0.0069(8) C27 0.0335(11) 0.0288(10) 0.0351(10) 0.0055(9) 0.0115(8) -0.0018(8) C28 0.0247(10) 0.0318(11) 0.0388(11) -0.0005(9) 0.0044(8) 0.0046(8) O1 0.0261(7) 0.0359(7) 0.0278(7) 0.0065(6) 0.0123(5) 0.0076(6) O2 0.0217(6) 0.0342(7) 0.0264(6) -0.0038(6) 0.0100(5) -0.0052(5) O3 0.0299(7) 0.0275(7) 0.0285(7) 0.0050(6) 0.0119(5) -0.0019(5) O4 0.0290(7) 0.0284(7) 0.0314(7) 0.0075(6) 0.0160(5) 0.0068(5) O5 0.0299(7) 0.0303(7) 0.0222(6) 0.0056(5) 0.0081(5) -0.0004(6) O6 0.0277(7) 0.0274(7) 0.0298(7) 0.0053(6) 0.0065(5) 0.0069(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.11476(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.348(2) yes N1 . C5 . 1.348(2) yes N2 . C6 . 1.339(2) yes N2 . C10 . 1.346(2) yes C1 . C2 . 1.397(2) yes C1 . C11 . 1.489(2) yes C2 . C3 . 1.390(2) yes C2 . H21 . 0.944 no C3 . C4 . 1.388(2) yes C3 . C20 . 1.488(2) yes C4 . C5 . 1.381(2) yes C4 . H41 . 0.918 no C5 . C6 . 1.488(2) yes C6 . C7 . 1.385(3) yes C7 . C8 . 1.374(3) yes C7 . H71 . 0.940 no C8 . C9 . 1.376(3) yes C8 . H81 . 0.959 no C9 . C10 . 1.374(3) yes C9 . H91 . 0.941 no C10 . H101 . 0.949 no C11 . C12 . 1.391(2) yes C11 . C16 . 1.399(2) yes C12 . C13 . 1.387(2) yes C12 . H121 . 0.947 no C13 . C14 . 1.393(2) yes C13 . O1 . 1.367(2) yes C14 . C15 . 1.399(3) yes C14 . O2 . 1.376(2) yes C15 . C16 . 1.388(3) yes C15 . O3 . 1.369(2) yes C16 . H161 . 0.943 no C17 . O1 . 1.428(2) yes C17 . H172 . 0.971 no C17 . H171 . 0.965 no C17 . H173 . 0.980 no C18 . O2 . 1.430(2) yes C18 . H182 . 0.983 no C18 . H181 . 0.994 no C18 . H183 . 0.985 no C19 . O3 . 1.431(2) yes C19 . H191 . 0.989 no C19 . H193 . 0.991 no C19 . H192 . 0.969 no C20 . C21 . 1.393(2) yes C20 . C25 . 1.391(2) yes C21 . C22 . 1.389(2) yes C21 . H211 . 0.941 no C22 . C23 . 1.393(2) yes C22 . O4 . 1.367(2) yes C23 . C24 . 1.391(2) yes C23 . O5 . 1.383(2) yes C24 . C25 . 1.392(2) yes C24 . O6 . 1.368(2) yes C25 . H251 . 0.935 no C26 . O4 . 1.428(2) yes C26 . H261 . 0.976 no C26 . H262 . 0.991 no C26 . H263 . 0.981 no C27 . O5 . 1.434(2) yes C27 . H272 . 0.979 no C27 . H271 . 0.984 no C27 . H273 . 0.989 no C28 . O6 . 1.428(2) yes C28 . H282 . 0.986 no C28 . H281 . 0.989 no C28 . H283 . 0.992 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C5 . 118.33(15) yes C6 . N2 . C10 . 118.22(18) yes N1 . C1 . C2 . 121.36(16) yes N1 . C1 . C11 . 117.21(15) yes C2 . C1 . C11 . 121.43(16) yes C1 . C2 . C3 . 120.02(16) yes C1 . C2 . H21 . 120.6 no C3 . C2 . H21 . 119.4 no C2 . C3 . C4 . 117.91(16) yes C2 . C3 . C20 . 121.79(16) yes C4 . C3 . C20 . 120.29(16) yes C3 . C4 . C5 . 119.28(16) yes C3 . C4 . H41 . 120.5 no C5 . C4 . H41 . 120.2 no C4 . C5 . N1 . 122.93(16) yes C4 . C5 . C6 . 120.13(16) yes N1 . C5 . C6 . 116.93(15) yes C5 . C6 . N2 . 116.50(16) yes C5 . C6 . C7 . 121.78(17) yes N2 . C6 . C7 . 121.71(18) yes C6 . C7 . C8 . 119.1(2) yes C6 . C7 . H71 . 118.5 no C8 . C7 . H71 . 122.3 no C7 . C8 . C9 . 119.7(2) yes C7 . C8 . H81 . 119.7 no C9 . C8 . H81 . 120.6 no C8 . C9 . C10 . 118.03(19) yes C8 . C9 . H91 . 121.4 no C10 . C9 . H91 . 120.5 no C9 . C10 . N2 . 123.2(2) yes C9 . C10 . H101 . 118.4 no N2 . C10 . H101 . 118.4 no C1 . C11 . C12 . 120.31(16) yes C1 . C11 . C16 . 119.70(16) yes C12 . C11 . C16 . 120.00(16) yes C11 . C12 . C13 . 120.27(16) yes C11 . C12 . H121 . 119.9 no C13 . C12 . H121 . 119.9 no C12 . C13 . C14 . 120.16(16) yes C12 . C13 . O1 . 124.15(16) yes C14 . C13 . O1 . 115.68(15) yes C13 . C14 . C15 . 119.49(16) yes C13 . C14 . O2 . 119.94(16) yes C15 . C14 . O2 . 120.56(16) yes C14 . C15 . C16 . 120.52(16) yes C14 . C15 . O3 . 114.57(15) yes C16 . C15 . O3 . 124.91(16) yes C11 . C16 . C15 . 119.55(16) yes C11 . C16 . H161 . 119.7 no C15 . C16 . H161 . 120.8 no O1 . C17 . H172 . 106.8 no O1 . C17 . H171 . 111.0 no H172 . C17 . H171 . 110.3 no O1 . C17 . H173 . 109.1 no H172 . C17 . H173 . 110.3 no H171 . C17 . H173 . 109.2 no O2 . C18 . H182 . 108.6 no O2 . C18 . H181 . 109.8 no H182 . C18 . H181 . 110.4 no O2 . C18 . H183 . 109.5 no H182 . C18 . H183 . 109.9 no H181 . C18 . H183 . 108.6 no O3 . C19 . H191 . 106.4 no O3 . C19 . H193 . 112.0 no H191 . C19 . H193 . 109.4 no O3 . C19 . H192 . 110.1 no H191 . C19 . H192 . 108.8 no H193 . C19 . H192 . 110.1 no C3 . C20 . C21 . 119.24(15) yes C3 . C20 . C25 . 120.38(15) yes C21 . C20 . C25 . 120.36(16) yes C20 . C21 . C22 . 119.59(16) yes C20 . C21 . H211 . 119.6 no C22 . C21 . H211 . 120.8 no C21 . C22 . C23 . 120.23(16) yes C21 . C22 . O4 . 124.17(16) yes C23 . C22 . O4 . 115.60(15) yes C22 . C23 . C24 . 119.96(15) yes C22 . C23 . O5 . 120.28(15) yes C24 . C23 . O5 . 119.75(16) yes C23 . C24 . C25 . 119.94(16) yes C23 . C24 . O6 . 115.53(15) yes C25 . C24 . O6 . 124.50(16) yes C24 . C25 . C20 . 119.87(16) yes C24 . C25 . H251 . 120.1 no C20 . C25 . H251 . 120.0 no O4 . C26 . H261 . 106.0 no O4 . C26 . H262 . 110.7 no H261 . C26 . H262 . 109.3 no O4 . C26 . H263 . 111.6 no H261 . C26 . H263 . 108.8 no H262 . C26 . H263 . 110.3 no O5 . C27 . H272 . 108.4 no O5 . C27 . H271 . 110.1 no H272 . C27 . H271 . 109.5 no O5 . C27 . H273 . 109.4 no H272 . C27 . H273 . 109.5 no H271 . C27 . H273 . 110.0 no O6 . C28 . H282 . 106.6 no O6 . C28 . H281 . 109.3 no H282 . C28 . H281 . 109.9 no O6 . C28 . H283 . 112.1 no H282 . C28 . H283 . 108.8 no H281 . C28 . H283 . 110.1 no C17 . O1 . C13 . 117.05(14) yes C18 . O2 . C14 . 112.09(14) yes C19 . O3 . C15 . 117.62(14) yes C26 . O4 . C22 . 116.45(14) yes C27 . O5 . C23 . 111.71(13) yes C28 . O6 . C24 . 117.29(15) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C8 . H81 . N2 4_564 153.90(7) 0.959 2.463 3.350(3) yes C9 . H91 . O2 4_464 146.72(5) 0.941 2.512 3.338(3) yes C17 . H171 . O5 2_667 155.42(5) 0.965 2.532 3.433(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 14/10/11 at 12:14:00 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 172,X'S) H ( 171,X'S) H ( 173,X'S) RIDE C ( 18,X'S) H ( 182,X'S) H ( 181,X'S) H ( 183,X'S) RIDE C ( 19,X'S) H ( 191,X'S) H ( 193,X'S) H ( 192,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) H ( 262,X'S) H ( 263,X'S) RIDE C ( 27,X'S) H ( 272,X'S) H ( 271,X'S) H ( 273,X'S) RIDE C ( 28,X'S) H ( 282,X'S) H ( 281,X'S) H ( 283,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 14/10/11 at 12:14:00 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; data_pkb236 _database_code_depnum_ccdc_archive 'CCDC 910297' #TrackingRef 'pkb236_triclinic.cif' _audit_creation_date 11-11-10 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'pkb236_123k_0m in P-1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 10.5992(2) _cell_length_b 11.0302(2) _cell_length_c 12.2247(3) _cell_angle_alpha 96.3390(10) _cell_angle_beta 108.9380(10) _cell_angle_gamma 108.6850(10) _cell_volume 1243.40(5) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C28 H28 N2 O4 # Dc = 1.22 Fooo = 516.00 Mu = 0.82 M = 456.54 # Found Formula = C28 H28 N2 O6 # Dc = 1.30 FOOO = 516.00 Mu = 0.92 M = 488.54 _chemical_formula_sum 'C28 H28 N2 O6' _chemical_formula_moiety 'C28 H28 N2 O6' _chemical_compound_source ? _chemical_formula_weight 488.54 _cell_measurement_reflns_used 9959 _cell_measurement_theta_min 3 _cell_measurement_theta_max 40 _cell_measurement_temperature 123 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.110 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_max 0.290 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.092 # Sheldrick geometric approximatio 0.99 0.99 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 43182 _reflns_number_total 11963 _diffrn_reflns_av_R_equivalents 0.023 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 11963 # Theoretical number of reflections is about 24103 _diffrn_reflns_theta_min 1.814 _diffrn_reflns_theta_max 36.318 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.149 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -17 _reflns_limit_h_max 16 _reflns_limit_k_min -18 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.24 _refine_diff_density_max 0.56 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 9173 _refine_ls_number_restraints 0 _refine_ls_number_parameters 325 _oxford_refine_ls_R_factor_ref 0.0403 _refine_ls_wR_factor_ref 0.0459 _refine_ls_goodness_of_fit_ref 1.0538 _refine_ls_shift/su_max 0.0009707 _refine_ls_shift/su_mean 0.0000808 # The values computed from all data _oxford_reflns_number_all 11948 _refine_ls_R_factor_all 0.0539 _refine_ls_wR_factor_all 0.0766 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 10262 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_gt 0.0496 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.232 0.232 0.728E-01 ; # Insert your own references if required - in alphabetical order loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.43656(6) 0.87841(6) 0.28422(5) 0.0168 1.0000 Uani . . . . . . N2 N 0.06404(6) 0.70837(7) 0.24412(5) 0.0225 1.0000 Uani . . . . . . C1 C 0.57083(7) 0.90707(6) 0.36498(5) 0.0160 1.0000 Uani . . . . . . C2 C 0.59427(7) 0.86365(6) 0.47023(6) 0.0173 1.0000 Uani . . . . . . C3 C 0.47594(6) 0.79133(6) 0.49507(5) 0.0161 1.0000 Uani . . . . . . C4 C 0.33890(6) 0.76975(6) 0.41521(5) 0.0156 1.0000 Uani . . . . . . C5 C 0.32353(6) 0.81037(6) 0.30980(5) 0.0148 1.0000 Uani . . . . . . C6 C 0.17727(7) 0.76657(6) 0.21460(5) 0.0162 1.0000 Uani . . . . . . C7 C 0.16137(7) 0.78092(8) 0.10007(6) 0.0213 1.0000 Uani . . . . . . C8 C 0.02406(8) 0.73214(9) 0.01218(7) 0.0271 1.0000 Uani . . . . . . C9 C -0.09394(8) 0.67131(9) 0.04054(7) 0.0262 1.0000 Uani . . . . . . C10 C -0.06892(8) 0.66201(9) 0.15745(7) 0.0262 1.0000 Uani . . . . . . C11 C 0.69296(7) 0.97416(6) 0.33071(5) 0.0160 1.0000 Uani . . . . . . C12 C 0.82838(7) 1.05686(6) 0.41589(5) 0.0174 1.0000 Uani . . . . . . C13 C 0.94263(7) 1.10873(6) 0.37940(6) 0.0169 1.0000 Uani . . . . . . C14 C 0.92181(7) 1.07786(6) 0.25905(6) 0.0178 1.0000 Uani . . . . . . C15 C 0.78437(7) 0.99871(6) 0.17417(6) 0.0188 1.0000 Uani . . . . . . C16 C 0.67043(7) 0.94639(6) 0.20999(6) 0.0184 1.0000 Uani . . . . . . C17 C 1.10298(9) 1.24077(8) 0.57383(7) 0.0272 1.0000 Uani . . . . . . C18 C 1.09046(10) 1.04285(9) 0.18593(9) 0.0336 1.0000 Uani . . . . . . C19 C 0.63731(10) 0.8962(1) -0.02991(7) 0.0332 1.0000 Uani . . . . . . C20 C 0.49330(6) 0.72592(6) 0.59556(5) 0.0160 1.0000 Uani . . . . . . C21 C 0.39895(7) 0.70965(6) 0.65563(6) 0.0182 1.0000 Uani . . . . . . C22 C 0.41445(7) 0.64263(6) 0.74630(6) 0.0171 1.0000 Uani . . . . . . C23 C 0.52356(7) 0.59230(6) 0.77791(5) 0.0157 1.0000 Uani . . . . . . C24 C 0.61470(7) 0.60597(6) 0.71499(5) 0.0161 1.0000 Uani . . . . . . C25 C 0.60028(7) 0.67330(6) 0.62445(6) 0.0171 1.0000 Uani . . . . . . C26 C 0.21864(11) 0.67183(11) 0.78435(11) 0.0381 1.0000 Uani . . . . . . C27 C 0.50173(10) 0.40167(8) 0.85483(8) 0.0297 1.0000 Uani . . . . . . C28 C 0.80118(7) 0.55254(7) 0.68072(7) 0.0209 1.0000 Uani . . . . . . O1 O 1.07944(6) 1.19011(6) 0.45337(5) 0.0235 1.0000 Uani . . . . . . O2 O 1.03418(6) 1.13352(5) 0.22515(5) 0.0241 1.0000 Uani . . . . . . O3 O 0.77371(7) 0.98119(6) 0.05900(5) 0.0278 1.0000 Uani . . . . . . O4 O 0.33122(6) 0.62298(6) 0.81279(5) 0.0249 1.0000 Uani . . . . . . O5 O 0.54705(6) 0.54145(5) 0.87673(4) 0.0198 1.0000 Uani . . . . . . O6 O 0.71508(6) 0.55130(6) 0.74985(5) 0.0220 1.0000 Uani . . . . . . H21 H 0.6916 0.8809 0.5243 0.0218 1.0000 Uiso R . . . . . H41 H 0.2572 0.7232 0.4286 0.0223 1.0000 Uiso R . . . . . H71 H 0.2435 0.8192 0.0824 0.0292 1.0000 Uiso R . . . . . H81 H 0.0119 0.7417 -0.0687 0.0342 1.0000 Uiso R . . . . . H91 H -0.1898 0.6392 -0.0177 0.0325 1.0000 Uiso R . . . . . H101 H -0.1517 0.6222 0.1781 0.0326 1.0000 Uiso R . . . . . H121 H 0.8430 1.0759 0.4979 0.0218 1.0000 Uiso R . . . . . H161 H 0.5756 0.8908 0.1527 0.0237 1.0000 Uiso R . . . . . H171 H 1.0391 1.2862 0.5778 0.0422 1.0000 Uiso R . . . . . H172 H 1.2038 1.3036 0.6100 0.0424 1.0000 Uiso R . . . . . H173 H 1.0915 1.1689 0.6179 0.0420 1.0000 Uiso R . . . . . H181 H 1.1461 1.0213 0.2552 0.0560 1.0000 Uiso R . . . . . H182 H 1.1559 1.0919 0.1530 0.0566 1.0000 Uiso R . . . . . H183 H 1.0173 0.9677 0.1310 0.0550 1.0000 Uiso R . . . . . H191 H 0.6476 0.8947 -0.1074 0.0514 1.0000 Uiso R . . . . . H192 H 0.6150 0.8056 -0.0174 0.0508 1.0000 Uiso R . . . . . H193 H 0.5584 0.9278 -0.0291 0.0517 1.0000 Uiso R . . . . . H211 H 0.3254 0.7463 0.6352 0.0238 1.0000 Uiso R . . . . . H251 H 0.6632 0.6845 0.5823 0.0216 1.0000 Uiso R . . . . . H261 H 0.1704 0.6532 0.8400 0.0580 1.0000 Uiso R . . . . . H262 H 0.2600 0.7695 0.7955 0.0580 1.0000 Uiso R . . . . . H263 H 0.1490 0.6298 0.7015 0.0580 1.0000 Uiso R . . . . . H271 H 0.5448 0.3697 0.8059 0.0483 1.0000 Uiso R . . . . . H272 H 0.5260 0.3798 0.9292 0.0458 1.0000 Uiso R . . . . . H273 H 0.3958 0.3622 0.8134 0.0482 1.0000 Uiso R . . . . . H281 H 0.8603 0.6414 0.6858 0.0323 1.0000 Uiso R . . . . . H282 H 0.8612 0.5038 0.7153 0.0314 1.0000 Uiso R . . . . . H283 H 0.7392 0.5044 0.5973 0.0324 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0146(2) 0.0205(2) 0.0156(2) 0.00621(17) 0.00563(16) 0.00650(17) N2 0.0150(2) 0.0333(3) 0.0187(2) 0.0103(2) 0.00543(18) 0.0082(2) C1 0.0145(2) 0.0181(2) 0.0145(2) 0.00534(18) 0.00463(18) 0.00564(18) C2 0.0133(2) 0.0207(2) 0.0164(2) 0.00765(19) 0.00441(18) 0.00491(19) C3 0.0134(2) 0.0179(2) 0.0168(2) 0.00721(18) 0.00482(18) 0.00559(18) C4 0.0130(2) 0.0183(2) 0.0150(2) 0.00701(18) 0.00435(18) 0.00541(18) C5 0.0130(2) 0.0181(2) 0.0138(2) 0.00584(17) 0.00474(17) 0.00641(18) C6 0.0141(2) 0.0205(2) 0.0142(2) 0.00641(18) 0.00445(18) 0.00696(19) C7 0.0167(3) 0.0309(3) 0.0162(2) 0.0099(2) 0.0052(2) 0.0083(2) C8 0.0207(3) 0.0404(4) 0.0180(3) 0.0105(3) 0.0043(2) 0.0110(3) C9 0.0171(3) 0.0360(4) 0.0188(3) 0.0065(3) 0.0009(2) 0.0075(3) C10 0.0163(3) 0.0368(4) 0.0226(3) 0.0108(3) 0.0050(2) 0.0075(3) C11 0.0159(2) 0.0173(2) 0.0148(2) 0.00556(18) 0.00591(18) 0.00550(19) C12 0.0162(2) 0.0204(2) 0.0147(2) 0.00523(19) 0.00585(19) 0.0056(2) C13 0.0160(2) 0.0174(2) 0.0159(2) 0.00457(18) 0.00595(19) 0.00453(19) C14 0.0203(3) 0.0150(2) 0.0177(2) 0.00433(18) 0.0097(2) 0.00372(19) C15 0.0229(3) 0.0160(2) 0.0149(2) 0.00332(18) 0.0087(2) 0.0027(2) C16 0.0198(3) 0.0173(2) 0.0151(2) 0.00427(18) 0.0066(2) 0.00328(19) C17 0.0225(3) 0.0314(3) 0.0187(3) 0.0007(2) 0.0044(2) 0.0040(3) C18 0.0282(4) 0.0317(4) 0.0397(4) -0.0018(3) 0.0203(3) 0.0057(3) C19 0.0318(4) 0.0371(4) 0.0166(3) -0.0012(3) 0.0090(3) -0.0019(3) C20 0.0136(2) 0.0175(2) 0.0165(2) 0.00677(18) 0.00476(18) 0.00560(18) C21 0.0159(2) 0.0202(2) 0.0219(3) 0.0097(2) 0.0083(2) 0.0085(2) C22 0.0162(2) 0.0178(2) 0.0199(2) 0.00726(19) 0.0088(2) 0.00671(19) C23 0.0162(2) 0.0162(2) 0.0146(2) 0.00535(17) 0.00520(18) 0.00601(18) C24 0.0144(2) 0.0187(2) 0.0156(2) 0.00574(18) 0.00452(18) 0.00743(19) C25 0.0152(2) 0.0211(2) 0.0166(2) 0.00762(19) 0.00609(19) 0.00789(19) C26 0.0377(5) 0.0505(5) 0.0552(6) 0.0309(5) 0.0338(4) 0.0309(4) C27 0.0393(4) 0.0199(3) 0.0272(3) 0.0111(2) 0.0106(3) 0.0083(3) C28 0.0182(3) 0.0197(3) 0.0273(3) 0.0060(2) 0.0100(2) 0.0090(2) O1 0.0161(2) 0.0295(2) 0.0175(2) 0.00333(18) 0.00505(16) 0.00134(18) O2 0.0264(2) 0.0192(2) 0.0260(2) 0.00335(17) 0.0170(2) 0.00135(18) O3 0.0303(3) 0.0278(3) 0.0150(2) 0.00095(18) 0.01060(19) -0.0028(2) O4 0.0258(2) 0.0310(3) 0.0318(3) 0.0172(2) 0.0200(2) 0.0161(2) O5 0.0241(2) 0.0197(2) 0.01602(19) 0.00813(15) 0.00699(17) 0.00824(17) O6 0.0207(2) 0.0306(2) 0.0226(2) 0.01316(19) 0.00935(18) 0.01625(19) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2524(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.3531(8) yes N1 . C5 . 1.3473(8) yes N2 . C6 . 1.3496(9) yes N2 . C10 . 1.3489(9) yes C1 . C2 . 1.3969(9) yes C1 . C11 . 1.4851(9) yes C2 . C3 . 1.4004(9) yes C2 . H21 . 0.970 no C3 . C4 . 1.3880(8) yes C3 . C20 . 1.4824(8) yes C4 . C5 . 1.3877(8) yes C4 . H41 . 0.930 no C5 . C6 . 1.4886(8) yes C6 . C7 . 1.3880(9) yes C7 . C8 . 1.3848(10) yes C7 . H71 . 0.943 no C8 . C9 . 1.3891(11) yes C8 . H81 . 0.977 no C9 . C10 . 1.3882(11) yes C9 . H91 . 0.953 no C10 . H101 . 0.973 no C11 . C12 . 1.3992(9) yes C11 . C16 . 1.3976(9) yes C12 . C13 . 1.3985(9) yes C12 . H121 . 0.952 no C13 . C14 . 1.3999(9) yes C13 . O1 . 1.3645(8) yes C14 . C15 . 1.4018(9) yes C14 . O2 . 1.3695(8) yes C15 . C16 . 1.3914(9) yes C15 . O3 . 1.3620(8) yes C16 . H161 . 0.964 no C17 . O1 . 1.4260(9) yes C17 . H171 . 0.972 no C17 . H172 . 0.984 no C17 . H173 . 1.005 no C18 . O2 . 1.4310(10) yes C18 . H181 . 0.965 no C18 . H182 . 0.962 no C18 . H183 . 0.931 no C19 . O3 . 1.4272(10) yes C19 . H191 . 0.987 no C19 . H192 . 0.992 no C19 . H193 . 1.007 no C20 . C21 . 1.4008(9) yes C20 . C25 . 1.3979(9) yes C21 . C22 . 1.3938(9) yes C21 . H211 . 0.965 no C22 . C23 . 1.4013(9) yes C22 . O4 . 1.3666(8) yes C23 . C24 . 1.4007(9) yes C23 . O5 . 1.3711(8) yes C24 . C25 . 1.3945(9) yes C24 . O6 . 1.3604(8) yes C25 . H251 . 0.954 no C26 . O4 . 1.4209(10) yes C26 . H261 . 0.978 no C26 . H262 . 0.999 no C26 . H263 . 0.989 no C27 . O5 . 1.4249(9) yes C27 . H271 . 0.962 no C27 . H272 . 0.942 no C27 . H273 . 0.988 no C28 . O6 . 1.4291(9) yes C28 . H281 . 0.962 no C28 . H282 . 0.983 no C28 . H283 . 0.988 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C5 . 118.14(5) yes C6 . N2 . C10 . 117.78(6) yes N1 . C1 . C2 . 121.91(6) yes N1 . C1 . C11 . 116.83(5) yes C2 . C1 . C11 . 120.92(5) yes C1 . C2 . C3 . 119.41(6) yes C1 . C2 . H21 . 120.3 no C3 . C2 . H21 . 120.3 no C2 . C3 . C4 . 118.12(5) yes C2 . C3 . C20 . 121.65(5) yes C4 . C3 . C20 . 119.87(5) yes C3 . C4 . C5 . 119.19(6) yes C3 . C4 . H41 . 121.1 no C5 . C4 . H41 . 119.6 no C4 . C5 . N1 . 122.99(5) yes C4 . C5 . C6 . 119.33(5) yes N1 . C5 . C6 . 117.40(5) yes C5 . C6 . N2 . 116.97(5) yes C5 . C6 . C7 . 120.36(6) yes N2 . C6 . C7 . 122.61(6) yes C6 . C7 . C8 . 118.76(6) yes C6 . C7 . H71 . 120.0 no C8 . C7 . H71 . 121.2 no C7 . C8 . C9 . 119.56(7) yes C7 . C8 . H81 . 119.3 no C9 . C8 . H81 . 121.1 no C8 . C9 . C10 . 118.11(7) yes C8 . C9 . H91 . 121.3 no C10 . C9 . H91 . 120.5 no C9 . C10 . N2 . 123.18(7) yes C9 . C10 . H101 . 118.2 no N2 . C10 . H101 . 118.6 no C1 . C11 . C12 . 121.73(5) yes C1 . C11 . C16 . 117.55(5) yes C12 . C11 . C16 . 120.63(6) yes C11 . C12 . C13 . 119.25(6) yes C11 . C12 . H121 . 120.3 no C13 . C12 . H121 . 120.4 no C12 . C13 . C14 . 120.35(6) yes C12 . C13 . O1 . 124.98(6) yes C14 . C13 . O1 . 114.67(6) yes C13 . C14 . C15 . 119.76(6) yes C13 . C14 . O2 . 119.17(6) yes C15 . C14 . O2 . 120.90(6) yes C14 . C15 . C16 . 120.09(6) yes C14 . C15 . O3 . 115.14(6) yes C16 . C15 . O3 . 124.76(6) yes C11 . C16 . C15 . 119.83(6) yes C11 . C16 . H161 . 119.1 no C15 . C16 . H161 . 121.0 no O1 . C17 . H171 . 111.1 no O1 . C17 . H172 . 105.4 no H171 . C17 . H172 . 109.8 no O1 . C17 . H173 . 111.1 no H171 . C17 . H173 . 110.8 no H172 . C17 . H173 . 108.5 no O2 . C18 . H181 . 108.0 no O2 . C18 . H182 . 104.9 no H181 . C18 . H182 . 107.8 no O2 . C18 . H183 . 111.6 no H181 . C18 . H183 . 111.5 no H182 . C18 . H183 . 112.6 no O3 . C19 . H191 . 106.8 no O3 . C19 . H192 . 109.1 no H191 . C19 . H192 . 108.0 no O3 . C19 . H193 . 111.8 no H191 . C19 . H193 . 110.3 no H192 . C19 . H193 . 110.7 no C3 . C20 . C21 . 120.85(5) yes C3 . C20 . C25 . 118.58(6) yes C21 . C20 . C25 . 120.46(6) yes C20 . C21 . C22 . 119.37(6) yes C20 . C21 . H211 . 120.0 no C22 . C21 . H211 . 120.7 no C21 . C22 . C23 . 120.61(6) yes C21 . C22 . O4 . 124.75(6) yes C23 . C22 . O4 . 114.62(6) yes C22 . C23 . C24 . 119.49(5) yes C22 . C23 . O5 . 119.00(6) yes C24 . C23 . O5 . 121.24(6) yes C23 . C24 . C25 . 120.23(6) yes C23 . C24 . O6 . 115.42(5) yes C25 . C24 . O6 . 124.34(6) yes C20 . C25 . C24 . 119.79(6) yes C20 . C25 . H251 . 119.5 no C24 . C25 . H251 . 120.7 no O4 . C26 . H261 . 108.1 no O4 . C26 . H262 . 109.9 no H261 . C26 . H262 . 107.8 no O4 . C26 . H263 . 110.9 no H261 . C26 . H263 . 110.2 no H262 . C26 . H263 . 110.0 no O5 . C27 . H271 . 111.0 no O5 . C27 . H272 . 107.6 no H271 . C27 . H272 . 112.2 no O5 . C27 . H273 . 108.6 no H271 . C27 . H273 . 109.1 no H272 . C27 . H273 . 108.2 no O6 . C28 . H281 . 110.8 no O6 . C28 . H282 . 105.2 no H281 . C28 . H282 . 110.7 no O6 . C28 . H283 . 110.2 no H281 . C28 . H283 . 111.4 no H282 . C28 . H283 . 108.2 no C17 . O1 . C13 . 117.41(6) yes C18 . O2 . C14 . 114.47(6) yes C19 . O3 . C15 . 116.99(6) yes C26 . O4 . C22 . 116.99(6) yes C27 . O5 . C23 . 116.03(5) yes C28 . O6 . C24 . 117.01(5) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C8 . H81 . O2 2_675 150.15(2) 0.977 2.489 3.3716(11) yes C9 . H91 . O5 1_454 165.00(2) 0.953 2.457 3.3867(11) yes C28 . H281 . O2 2_776 151.64(2) 0.962 2.331 3.2102(11) yes _iucr_refine_instruction_details_constraints ; # # Punched on 10/11/11 at 08:10:52 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 172,X'S) H ( 171,X'S) H ( 173,X'S) RIDE C ( 18,X'S) H ( 182,X'S) H ( 181,X'S) H ( 183,X'S) RIDE C ( 19,X'S) H ( 191,X'S) H ( 193,X'S) H ( 192,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) H ( 262,X'S) H ( 263,X'S) RIDE C ( 27,X'S) H ( 272,X'S) H ( 271,X'S) H ( 273,X'S) RIDE C ( 28,X'S) H ( 282,X'S) H ( 281,X'S) H ( 283,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 10/11/11 at 08:10:52 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; data_pka159 _database_code_depnum_ccdc_archive 'CCDC 925640' #TrackingRef 'PKA159revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C32 H28 Ir N4 O), C H4 O, 2(F6 P), 2(H2 O)' _chemical_formula_sum 'C65 H64 F12 Ir2 N8 O5 P2' _chemical_formula_weight 1711.59 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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)/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.4951(12) _cell_length_b 13.0662(11) _cell_length_c 16.4258(11) _cell_angle_alpha 90.00 _cell_angle_beta 113.986(5) _cell_angle_gamma 90.00 _cell_volume 3234.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10215 _cell_measurement_theta_min 4.97 _cell_measurement_theta_max 67.33 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1676 _exptl_absorpt_coefficient_mu 4.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3177 _exptl_absorpt_correction_T_max 0.3177 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22644 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_unetI/netI 0.0397 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7004 _reflns_number_gt 6568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _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^)+(0.0341P)^2^+10.1289P] 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_number_reflns 7004 _refine_ls_number_parameters 446 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _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 0.276168(11) 0.182259(13) 0.121524(11) 0.02417(7) Uani 1 1 d . . . N1 N 0.2071(3) 0.2243(3) -0.0152(3) 0.0276(8) Uani 1 1 d . . . O1 O 0.1550(2) 0.2547(3) 0.1147(2) 0.0278(7) Uani 1 1 d . . . N2 N -0.0733(3) 0.3969(3) 0.0931(3) 0.0331(9) Uani 1 1 d . . . C1 C 0.2358(3) 0.2070(4) -0.0792(3) 0.0311(10) Uani 1 1 d . . . H1A H 0.2893 0.1696 -0.0647 0.037 Uiso 1 1 calc R . . C2 C 0.1910(4) 0.2413(4) -0.1652(3) 0.0353(11) Uani 1 1 d . . . H2A H 0.2131 0.2277 -0.2093 0.042 Uiso 1 1 calc R . . C3 C 0.1136(4) 0.2955(4) -0.1863(3) 0.0364(11) Uani 1 1 d . . . H3A H 0.0820 0.3210 -0.2450 0.044 Uiso 1 1 calc R . . C4 C 0.0824(4) 0.3124(4) -0.1212(4) 0.0368(11) Uani 1 1 d . . . H4A H 0.0285 0.3486 -0.1348 0.044 Uiso 1 1 calc R . . C5 C 0.1308(3) 0.2760(4) -0.0357(3) 0.0278(9) Uani 1 1 d . . . C6 C 0.1034(3) 0.2892(4) 0.0405(3) 0.0269(9) Uani 1 1 d . . . C7 C 0.0235(3) 0.3392(4) 0.0259(3) 0.0285(9) Uani 1 1 d . . . H7A H -0.0146 0.3616 -0.0322 0.034 Uiso 1 1 calc R . . C8 C 0.0009(3) 0.3554(4) 0.0973(3) 0.0311(10) Uani 1 1 d . . . H8A H 0.0427 0.3348 0.1544 0.037 Uiso 1 1 calc R . . C9 C -0.1428(4) 0.4299(5) 0.0097(4) 0.0454(13) Uani 1 1 d . . . H9A H -0.1179 0.4770 -0.0206 0.068 Uiso 1 1 calc R . . H9B H -0.1894 0.4649 0.0216 0.068 Uiso 1 1 calc R . . H9C H -0.1681 0.3702 -0.0283 0.068 Uiso 1 1 calc R . . C10 C -0.0904(4) 0.4059(5) 0.1735(4) 0.0427(12) Uani 1 1 d . . . H10A H -0.0381 0.3828 0.2252 0.064 Uiso 1 1 calc R . . H10B H -0.1415 0.3634 0.1673 0.064 Uiso 1 1 calc R . . H10C H -0.1029 0.4775 0.1819 0.064 Uiso 1 1 calc R . . N3 N 0.3460(3) 0.3140(3) 0.1433(3) 0.0293(8) Uani 1 1 d . . . C11 C 0.3868(3) 0.1290(4) 0.1163(3) 0.0305(10) Uani 1 1 d . . . C12 C 0.4044(3) 0.0289(4) 0.0980(3) 0.0361(11) Uani 1 1 d . . . H12A H 0.3603 -0.0226 0.0859 0.043 Uiso 1 1 calc R . . C13 C 0.4864(4) 0.0045(5) 0.0975(4) 0.0482(14) Uani 1 1 d . . . H13A H 0.4981 -0.0640 0.0862 0.058 Uiso 1 1 calc R . . C14 C 0.5505(4) 0.0774(6) 0.1129(4) 0.0500(16) Uani 1 1 d . . . H14A H 0.6058 0.0593 0.1116 0.060 Uiso 1 1 calc R . . C15 C 0.5354(4) 0.1761(5) 0.1301(4) 0.0447(14) Uani 1 1 d . . . H15A H 0.5799 0.2265 0.1402 0.054 Uiso 1 1 calc R . . C16 C 0.4538(3) 0.2032(4) 0.1327(3) 0.0328(11) Uani 1 1 d . . . C17 C 0.4314(3) 0.3053(4) 0.1484(3) 0.0344(11) Uani 1 1 d . . . C18 C 0.4848(4) 0.3906(5) 0.1661(4) 0.0474(14) Uani 1 1 d . . . H18A H 0.5433 0.3849 0.1690 0.057 Uiso 1 1 calc R . . C19 C 0.4535(5) 0.4845(5) 0.1796(4) 0.0536(17) Uani 1 1 d . . . H19A H 0.4904 0.5434 0.1921 0.064 Uiso 1 1 calc R . . C20 C 0.3682(5) 0.4920(5) 0.1746(4) 0.0497(15) Uani 1 1 d . . . H20A H 0.3457 0.5558 0.1839 0.060 Uiso 1 1 calc R . . C21 C 0.3164(4) 0.4055(4) 0.1560(4) 0.0385(11) Uani 1 1 d . . . H21A H 0.2575 0.4108 0.1521 0.046 Uiso 1 1 calc R . . N4 N 0.2166(3) 0.0438(3) 0.1114(3) 0.0289(8) Uani 1 1 d . . . C22 C 0.3280(3) 0.1429(4) 0.2504(3) 0.0278(9) Uani 1 1 d . . . C23 C 0.3872(3) 0.1975(4) 0.3242(3) 0.0335(10) Uani 1 1 d . . . H23A H 0.4095 0.2614 0.3148 0.040 Uiso 1 1 calc R . . C24 C 0.4141(4) 0.1605(5) 0.4107(3) 0.0405(12) Uani 1 1 d . . . H24A H 0.4538 0.1995 0.4595 0.049 Uiso 1 1 calc R . . C25 C 0.3832(4) 0.0677(5) 0.4258(3) 0.0436(13) Uani 1 1 d . . . H25A H 0.4009 0.0430 0.4849 0.052 Uiso 1 1 calc R . . C26 C 0.3268(4) 0.0106(5) 0.3552(4) 0.0424(12) Uani 1 1 d . . . H26A H 0.3067 -0.0541 0.3657 0.051 Uiso 1 1 calc R . . C27 C 0.2988(3) 0.0469(4) 0.2683(3) 0.0317(10) Uani 1 1 d . . . C28 C 0.2386(3) -0.0082(4) 0.1896(3) 0.0321(10) Uani 1 1 d . . . C29 C 0.2069(4) -0.1064(5) 0.1906(4) 0.0450(13) Uani 1 1 d . . . H29A H 0.2249 -0.1434 0.2449 0.054 Uiso 1 1 calc R . . C30 C 0.1491(5) -0.1497(5) 0.1119(5) 0.0605(19) Uani 1 1 d . . . H30A H 0.1259 -0.2162 0.1117 0.073 Uiso 1 1 calc R . . C31 C 0.1253(5) -0.0960(5) 0.0337(5) 0.0586(18) Uani 1 1 d . . . H31A H 0.0849 -0.1247 -0.0209 0.070 Uiso 1 1 calc R . . C32 C 0.1609(4) 0.0000(4) 0.0352(3) 0.0380(11) Uani 1 1 d . . . H32A H 0.1455 0.0361 -0.0193 0.046 Uiso 1 1 calc R . . P1 P 0.16465(10) -0.07217(12) -0.21541(10) 0.0417(3) Uani 1 1 d . . . F10 F 0.1037(4) -0.1596(4) -0.2062(4) 0.105(2) Uani 1 1 d . . . F11 F 0.1046(3) 0.0092(4) -0.1934(3) 0.0786(13) Uani 1 1 d . . . F12 F 0.1018(3) -0.0573(4) -0.3191(3) 0.0832(14) Uani 1 1 d . . . F13 F 0.2264(4) -0.1497(4) -0.2354(4) 0.0994(18) Uani 1 1 d . . . F14 F 0.2245(3) 0.0187(3) -0.2226(3) 0.0730(12) Uani 1 1 d . . . F15 F 0.2253(3) -0.0789(4) -0.1124(3) 0.0683(11) Uani 1 1 d . . . O100 O 0.3408(9) -0.1811(9) 0.4803(9) 0.075(4) Uani 0.50 1 d P A 1 O200 O 0.2870(7) -0.2177(6) 0.4429(7) 0.059(3) Uani 0.50 1 d P B 2 H200 H 0.2397 -0.2499 0.4325 0.088 Uiso 0.50 1 calc PR B 2 C200 C 0.3481(7) -0.2384(9) 0.5301(7) 0.039(2) Uani 0.50 1 d P B 2 H20B H 0.3763 -0.1744 0.5590 0.058 Uiso 0.50 1 calc PR B 2 H20C H 0.3934 -0.2858 0.5284 0.058 Uiso 0.50 1 calc PR B 2 H20D H 0.3171 -0.2694 0.5637 0.058 Uiso 0.50 1 calc PR B 2 O300 O 0.3704(11) -0.2719(9) 0.6467(8) 0.099(5) Uani 0.50 1 d P C 1 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 0.01899(10) 0.03507(11) 0.01784(10) -0.00311(6) 0.00685(7) -0.00292(6) N1 0.0256(19) 0.034(2) 0.0232(19) -0.0040(15) 0.0099(16) -0.0057(16) O1 0.0221(15) 0.0432(18) 0.0156(15) -0.0018(12) 0.0051(13) 0.0032(13) N2 0.026(2) 0.037(2) 0.037(2) 0.0003(17) 0.0136(18) -0.0004(16) C1 0.028(2) 0.042(3) 0.023(2) -0.0016(19) 0.0103(19) -0.006(2) C2 0.043(3) 0.042(3) 0.026(2) -0.006(2) 0.019(2) -0.008(2) C3 0.045(3) 0.043(3) 0.015(2) 0.0014(19) 0.006(2) -0.003(2) C4 0.036(3) 0.042(3) 0.028(3) 0.000(2) 0.009(2) 0.002(2) C5 0.026(2) 0.033(2) 0.022(2) -0.0033(18) 0.0075(18) -0.0044(18) C6 0.024(2) 0.034(2) 0.022(2) -0.0040(17) 0.0082(18) -0.0050(18) C7 0.023(2) 0.038(2) 0.019(2) 0.0013(17) 0.0024(18) -0.0019(18) C8 0.026(2) 0.033(2) 0.034(3) 0.000(2) 0.012(2) -0.0033(18) C9 0.030(3) 0.049(3) 0.053(4) 0.004(3) 0.013(3) 0.008(2) C10 0.040(3) 0.050(3) 0.046(3) -0.001(2) 0.025(3) 0.003(2) N3 0.027(2) 0.044(2) 0.0183(18) -0.0016(15) 0.0105(16) -0.0087(16) C11 0.022(2) 0.054(3) 0.0120(19) 0.0008(18) 0.0030(17) -0.001(2) C12 0.030(2) 0.054(3) 0.022(2) 0.002(2) 0.009(2) 0.008(2) C13 0.042(3) 0.070(4) 0.036(3) 0.005(3) 0.020(3) 0.018(3) C14 0.029(3) 0.094(5) 0.028(3) 0.007(3) 0.012(2) 0.018(3) C15 0.027(3) 0.079(4) 0.028(3) 0.007(3) 0.011(2) -0.002(3) C16 0.021(2) 0.064(3) 0.014(2) 0.004(2) 0.0074(18) -0.003(2) C17 0.029(2) 0.053(3) 0.018(2) 0.0035(19) 0.006(2) -0.010(2) C18 0.038(3) 0.065(4) 0.037(3) 0.000(3) 0.013(3) -0.020(3) C19 0.058(4) 0.058(4) 0.035(3) -0.001(3) 0.010(3) -0.032(3) C20 0.068(4) 0.041(3) 0.028(3) -0.002(2) 0.007(3) -0.015(3) C21 0.045(3) 0.038(3) 0.031(3) -0.002(2) 0.014(2) -0.009(2) N4 0.0257(19) 0.040(2) 0.0231(19) -0.0043(16) 0.0118(16) -0.0051(16) C22 0.023(2) 0.039(2) 0.024(2) -0.0010(18) 0.0127(19) 0.0026(18) C23 0.023(2) 0.050(3) 0.024(2) -0.005(2) 0.0060(19) -0.002(2) C24 0.028(3) 0.069(4) 0.016(2) -0.006(2) 0.001(2) 0.003(2) C25 0.041(3) 0.067(4) 0.020(2) 0.006(2) 0.010(2) 0.005(3) C26 0.040(3) 0.057(3) 0.036(3) 0.007(2) 0.021(2) 0.004(2) C27 0.029(2) 0.040(2) 0.033(2) 0.002(2) 0.019(2) 0.002(2) C28 0.033(2) 0.040(3) 0.030(2) -0.001(2) 0.020(2) -0.002(2) C29 0.051(3) 0.052(3) 0.040(3) -0.001(2) 0.027(3) -0.015(3) C30 0.080(5) 0.054(4) 0.059(4) -0.011(3) 0.040(4) -0.030(4) C31 0.064(4) 0.062(4) 0.052(4) -0.023(3) 0.026(3) -0.036(3) C32 0.037(3) 0.049(3) 0.025(2) -0.010(2) 0.009(2) -0.013(2) P1 0.0376(7) 0.0480(8) 0.0329(7) -0.0018(6) 0.0077(6) -0.0046(6) F10 0.087(4) 0.087(3) 0.101(4) 0.036(3) -0.002(3) -0.047(3) F11 0.055(3) 0.099(3) 0.086(3) 0.016(3) 0.034(2) 0.028(2) F12 0.095(4) 0.090(3) 0.042(2) 0.007(2) 0.006(2) -0.022(3) F13 0.114(4) 0.077(3) 0.105(4) -0.033(3) 0.042(4) 0.024(3) F14 0.068(3) 0.071(3) 0.084(3) -0.005(2) 0.036(3) -0.020(2) F15 0.062(3) 0.082(3) 0.046(2) -0.0043(19) 0.006(2) 0.007(2) O100 0.086(9) 0.087(8) 0.073(8) 0.029(7) 0.053(7) 0.051(7) O200 0.045(5) 0.021(4) 0.083(7) -0.015(4) -0.001(5) -0.012(4) C200 0.024(5) 0.045(6) 0.036(6) -0.002(5) 0.001(4) 0.005(4) O300 0.178(15) 0.061(7) 0.063(7) 0.015(6) 0.055(9) 0.006(8) _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 1.987(5) . ? Ir1 C22 2.002(5) . ? Ir1 N3 2.021(4) . ? Ir1 N4 2.033(4) . ? Ir1 N1 2.137(4) . ? Ir1 O1 2.173(3) . ? N1 C1 1.335(6) . ? N1 C5 1.345(6) . ? O1 C6 1.253(6) . ? N2 C8 1.314(6) . ? N2 C9 1.449(7) . ? N2 C10 1.463(7) . ? C1 C2 1.377(7) . ? C1 H1A 0.9500 . ? C2 C3 1.375(8) . ? C2 H2A 0.9500 . ? C3 C4 1.380(7) . ? C3 H3A 0.9500 . ? C4 C5 1.387(7) . ? C4 H4A 0.9500 . ? C5 C6 1.503(6) . ? C6 C7 1.402(6) . ? C7 C8 1.385(7) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N3 C21 1.340(7) . ? N3 C17 1.380(6) . ? C11 C12 1.398(7) . ? C11 C16 1.412(7) . ? C12 C13 1.394(7) . ? C12 H12A 0.9500 . ? C13 C14 1.367(9) . ? C13 H13A 0.9500 . ? C14 C15 1.364(9) . ? C14 H14A 0.9500 . ? C15 C16 1.410(7) . ? C15 H15A 0.9500 . ? C16 C17 1.434(8) . ? C17 C18 1.377(7) . ? C18 C19 1.384(10) . ? C18 H18A 0.9500 . ? C19 C20 1.379(10) . ? C19 H19A 0.9500 . ? C20 C21 1.374(8) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? N4 C32 1.343(6) . ? N4 C28 1.365(6) . ? C22 C23 1.403(7) . ? C22 C27 1.416(7) . ? C23 C24 1.392(7) . ? C23 H23A 0.9500 . ? C24 C25 1.376(8) . ? C24 H24A 0.9500 . ? C25 C26 1.375(8) . ? C25 H25A 0.9500 . ? C26 C27 1.393(7) . ? C26 H26A 0.9500 . ? C27 C28 1.459(7) . ? C28 C29 1.389(7) . ? C29 C30 1.377(9) . ? C29 H29A 0.9500 . ? C30 C31 1.374(10) . ? C30 H30A 0.9500 . ? C31 C32 1.380(8) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? P1 F13 1.563(5) . ? P1 F10 1.570(5) . ? P1 F14 1.579(4) . ? P1 F15 1.580(4) . ? P1 F11 1.592(5) . ? P1 F12 1.606(4) . ? O200 C200 1.402(15) . ? O200 H200 0.8400 . ? C200 H20B 0.9800 . ? C200 H20C 0.9800 . ? C200 H20D 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 C11 Ir1 C22 87.19(18) . . ? C11 Ir1 N3 80.72(19) . . ? C22 Ir1 N3 93.70(18) . . ? C11 Ir1 N4 96.11(19) . . ? C22 Ir1 N4 80.92(18) . . ? N3 Ir1 N4 173.92(16) . . ? C11 Ir1 N1 98.69(16) . . ? C22 Ir1 N1 173.76(16) . . ? N3 Ir1 N1 89.36(15) . . ? N4 Ir1 N1 96.26(15) . . ? C11 Ir1 O1 172.73(16) . . ? C22 Ir1 O1 98.89(15) . . ? N3 Ir1 O1 94.84(15) . . ? N4 Ir1 O1 88.81(14) . . ? N1 Ir1 O1 75.40(13) . . ? C1 N1 C5 118.9(4) . . ? C1 N1 Ir1 125.1(3) . . ? C5 N1 Ir1 115.9(3) . . ? C6 O1 Ir1 116.9(3) . . ? C8 N2 C9 122.3(4) . . ? C8 N2 C10 120.2(5) . . ? C9 N2 C10 117.5(4) . . ? N1 C1 C2 122.5(5) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? C3 C2 C1 118.9(5) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 119.2(5) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C3 C4 C5 119.2(5) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? N1 C5 C4 121.3(4) . . ? N1 C5 C6 114.6(4) . . ? C4 C5 C6 124.0(4) . . ? O1 C6 C7 123.6(4) . . ? O1 C6 C5 117.0(4) . . ? C7 C6 C5 119.4(4) . . ? C8 C7 C6 119.0(4) . . ? C8 C7 H7A 120.5 . . ? C6 C7 H7A 120.5 . . ? N2 C8 C7 125.8(5) . . ? N2 C8 H8A 117.1 . . ? C7 C8 H8A 117.1 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C21 N3 C17 119.5(4) . . ? C21 N3 Ir1 124.7(3) . . ? C17 N3 Ir1 115.7(3) . . ? C12 C11 C16 118.0(5) . . ? C12 C11 Ir1 127.7(4) . . ? C16 C11 Ir1 114.3(4) . . ? C13 C12 C11 120.1(5) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 121.3(6) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C15 C14 C13 120.3(5) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C14 C15 C16 120.1(6) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C15 C16 C11 120.3(5) . . ? C15 C16 C17 124.0(5) . . ? C11 C16 C17 115.7(4) . . ? C18 C17 N3 119.7(5) . . ? C18 C17 C16 126.9(5) . . ? N3 C17 C16 113.4(4) . . ? C17 C18 C19 120.3(6) . . ? C17 C18 H18A 119.9 . . ? C19 C18 H18A 119.9 . . ? C20 C19 C18 119.4(5) . . ? C20 C19 H19A 120.3 . . ? C18 C19 H19A 120.3 . . ? C21 C20 C19 118.9(6) . . ? C21 C20 H20A 120.6 . . ? C19 C20 H20A 120.6 . . ? N3 C21 C20 122.3(6) . . ? N3 C21 H21A 118.8 . . ? C20 C21 H21A 118.8 . . ? C32 N4 C28 118.9(4) . . ? C32 N4 Ir1 125.5(4) . . ? C28 N4 Ir1 115.5(3) . . ? C23 C22 C27 116.6(4) . . ? C23 C22 Ir1 129.1(4) . . ? C27 C22 Ir1 114.3(3) . . ? C24 C23 C22 121.7(5) . . ? C24 C23 H23A 119.1 . . ? C22 C23 H23A 119.1 . . ? C25 C24 C23 120.1(5) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C26 C25 C24 120.0(5) . . ? C26 C25 H25A 120.0 . . ? C24 C25 H25A 120.0 . . ? C25 C26 C27 120.6(5) . . ? C25 C26 H26A 119.7 . . ? C27 C26 H26A 119.7 . . ? C26 C27 C22 121.0(5) . . ? C26 C27 C28 124.3(5) . . ? C22 C27 C28 114.8(4) . . ? N4 C28 C29 120.9(5) . . ? N4 C28 C27 114.4(4) . . ? C29 C28 C27 124.7(5) . . ? C30 C29 C28 119.2(6) . . ? C30 C29 H29A 120.4 . . ? C28 C29 H29A 120.4 . . ? C31 C30 C29 119.6(6) . . ? C31 C30 H30A 120.2 . . ? C29 C30 H30A 120.2 . . ? C30 C31 C32 119.3(6) . . ? C30 C31 H31A 120.4 . . ? C32 C31 H31A 120.4 . . ? N4 C32 C31 122.0(5) . . ? N4 C32 H32A 119.0 . . ? C31 C32 H32A 119.0 . . ? F13 P1 F10 92.7(4) . . ? F13 P1 F14 89.5(3) . . ? F10 P1 F14 177.7(3) . . ? F13 P1 F15 90.3(3) . . ? F10 P1 F15 90.4(3) . . ? F14 P1 F15 88.8(3) . . ? F13 P1 F11 178.0(3) . . ? F10 P1 F11 89.0(3) . . ? F14 P1 F11 88.8(3) . . ? F15 P1 F11 88.6(2) . . ? F13 P1 F12 92.9(3) . . ? F10 P1 F12 91.6(3) . . ? F14 P1 F12 89.0(3) . . ? F15 P1 F12 176.1(3) . . ? F11 P1 F12 88.1(3) . . ? C200 O200 H200 109.5 . . ? O200 C200 H20B 109.5 . . ? O200 C200 H20C 109.5 . . ? H20B C200 H20C 109.5 . . ? O200 C200 H20D 109.5 . . ? H20B C200 H20D 109.5 . . ? H20C C200 H20D 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.437 _refine_diff_density_min -1.700 _refine_diff_density_rms 0.121 data_pka185 _database_code_depnum_ccdc_archive 'CCDC 925641' #TrackingRef 'PKA185revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C37 H29 Ir N5), 2(F6 P), C7 H8' _chemical_formula_sum 'C81 H66 F12 Ir2 N10 P2' _chemical_formula_weight 1853.82 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 Pbcn _symmetry_space_group_name_Hall -P2n2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 20.941(4) _cell_length_b 20.129(4) _cell_length_c 16.916(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7130(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10077 _cell_measurement_theta_min 5.63 _cell_measurement_theta_max 61.22 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.727 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3656 _exptl_absorpt_coefficient_mu 3.860 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5433 _exptl_absorpt_correction_T_max 0.8609 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; One PF6 is highly disordered over a special position, only the highest occupancy positions could be modelled. The Ueq's of the atoms affected are large due to additional disorder that could not be easily modelled. Restraints were used to regulate disordered regions. ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 123452 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_unetI/netI 0.0199 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.50 _reflns_number_total 7385 _reflns_number_gt 6759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _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^)+(0.0162P)^2^+31.8093P] 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_number_reflns 7385 _refine_ls_number_parameters 529 _refine_ls_number_restraints 47 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.239 _refine_ls_restrained_S_all 1.254 _refine_ls_shift/su_max 0.003 _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 0.686371(9) 0.542456(10) 0.489193(10) 0.02837(7) Uani 1 1 d . . . N1 N 0.6495(2) 0.4720(2) 0.4059(2) 0.0304(9) Uani 1 1 d . . . N2 N 0.7334(2) 0.5680(2) 0.3774(2) 0.0288(9) Uani 1 1 d . . . C1 C 0.5997(3) 0.4315(3) 0.4168(3) 0.0373(12) Uani 1 1 d . . . H1A H 0.5755 0.4356 0.4641 0.045 Uiso 1 1 calc R . . C2 C 0.5821(3) 0.3838(3) 0.3625(3) 0.0420(13) Uani 1 1 d . . . H2A H 0.5459 0.3563 0.3717 0.050 Uiso 1 1 calc R . . C3 C 0.6180(3) 0.3769(3) 0.2944(3) 0.0424(13) Uani 1 1 d . . . H3A H 0.6070 0.3443 0.2562 0.051 Uiso 1 1 calc R . . C4 C 0.6700(3) 0.4178(3) 0.2826(3) 0.0343(11) Uani 1 1 d . . . H4A H 0.6953 0.4135 0.2363 0.041 Uiso 1 1 calc R . . C5 C 0.6847(2) 0.4652(2) 0.3391(3) 0.0305(10) Uani 1 1 d . . . C6 C 0.7371(2) 0.5135(3) 0.3304(3) 0.0303(11) Uani 1 1 d . . . C7 C 0.7877(3) 0.5037(3) 0.2785(3) 0.0400(12) Uani 1 1 d . . . H7A H 0.7898 0.4653 0.2459 0.048 Uiso 1 1 calc R . . C8 C 0.8353(3) 0.5520(3) 0.2755(3) 0.0470(15) Uani 1 1 d . . . H8A H 0.8728 0.5446 0.2451 0.056 Uiso 1 1 calc R . . C9 C 0.8280(3) 0.6103(3) 0.3168(3) 0.0440(14) Uani 1 1 d . . . H9A H 0.8591 0.6444 0.3125 0.053 Uiso 1 1 calc R . . C10 C 0.7742(3) 0.6190(3) 0.3655(3) 0.0348(12) Uani 1 1 d . . . C11 C 0.7551(3) 0.6842(3) 0.3963(3) 0.0424(14) Uani 1 1 d . . . C12 C 0.6974(3) 0.7161(3) 0.3790(4) 0.0523(17) Uani 1 1 d . . . H12A H 0.6613 0.6971 0.3535 0.063 Uiso 1 1 calc R . . C13 C 0.7028(5) 0.7810(4) 0.4064(5) 0.075(3) Uani 1 1 d . . . H13A H 0.6710 0.8146 0.4032 0.090 Uiso 1 1 calc R . . C14 C 0.7617(5) 0.7876(4) 0.4386(5) 0.078(3) Uani 1 1 d . . . H14A H 0.7778 0.8267 0.4630 0.094 Uiso 1 1 calc R . . N3 N 0.7944(3) 0.7291(3) 0.4304(4) 0.0634(17) Uani 1 1 d . . . C15 C 0.8565(4) 0.7160(5) 0.4636(5) 0.076(3) Uani 1 1 d . . . H15A H 0.8629 0.6679 0.4681 0.114 Uiso 1 1 calc R . . H15B H 0.8594 0.7363 0.5162 0.114 Uiso 1 1 calc R . . H15C H 0.8895 0.7349 0.4292 0.114 Uiso 1 1 calc R . . C16 C 0.6455(3) 0.4992(3) 0.5821(3) 0.0379(13) Uani 1 1 d . . . C17 C 0.5854(3) 0.5127(4) 0.6142(3) 0.0503(17) Uani 1 1 d . . . H17A H 0.5614 0.5491 0.5942 0.060 Uiso 1 1 calc R . . C18 C 0.5600(4) 0.4743(4) 0.6743(4) 0.067(2) Uani 1 1 d . . . H18A H 0.5191 0.4849 0.6952 0.080 Uiso 1 1 calc R . . C19 C 0.5932(4) 0.4211(5) 0.7041(4) 0.071(3) Uani 1 1 d . . . H19A H 0.5750 0.3949 0.7450 0.085 Uiso 1 1 calc R . . C20 C 0.6530(4) 0.4053(4) 0.6751(4) 0.063(2) Uani 1 1 d . . . H20A H 0.6762 0.3687 0.6958 0.076 Uiso 1 1 calc R . . C21 C 0.6790(3) 0.4451(3) 0.6133(3) 0.0444(15) Uani 1 1 d . . . C22 C 0.7418(3) 0.4338(3) 0.5788(3) 0.0450(15) Uani 1 1 d . . . C23 C 0.7876(4) 0.3892(4) 0.6054(5) 0.064(2) Uani 1 1 d . . . H23A H 0.7779 0.3606 0.6484 0.077 Uiso 1 1 calc R . . C24 C 0.8462(5) 0.3860(4) 0.5708(5) 0.075(2) Uani 1 1 d . . . H24A H 0.8772 0.3553 0.5894 0.090 Uiso 1 1 calc R . . C25 C 0.8601(3) 0.4278(4) 0.5085(5) 0.0595(18) Uani 1 1 d . . . H25A H 0.9008 0.4266 0.4838 0.071 Uiso 1 1 calc R . . C26 C 0.8139(3) 0.4711(3) 0.4831(4) 0.0448(13) Uani 1 1 d . . . H26A H 0.8235 0.4994 0.4397 0.054 Uiso 1 1 calc R . . N4 N 0.7558(2) 0.4753(2) 0.5165(3) 0.0363(10) Uani 1 1 d . . . C27 C 0.7223(2) 0.6102(3) 0.5645(3) 0.0304(11) Uani 1 1 d . . . C28 C 0.7817(3) 0.6096(3) 0.6039(3) 0.0387(13) Uani 1 1 d . . . H28A H 0.8115 0.5752 0.5931 0.046 Uiso 1 1 calc R . . C29 C 0.7972(3) 0.6587(3) 0.6581(3) 0.0473(15) Uani 1 1 d . . . H29A H 0.8375 0.6577 0.6838 0.057 Uiso 1 1 calc R . . C30 C 0.7546(4) 0.7091(3) 0.6750(3) 0.0515(16) Uani 1 1 d . . . H30A H 0.7653 0.7419 0.7131 0.062 Uiso 1 1 calc R . . C31 C 0.6963(3) 0.7118(3) 0.6364(3) 0.0447(14) Uani 1 1 d . . . H31A H 0.6670 0.7466 0.6477 0.054 Uiso 1 1 calc R . . C32 C 0.6808(3) 0.6631(3) 0.5807(3) 0.0338(11) Uani 1 1 d . . . C33 C 0.6217(3) 0.6642(3) 0.5344(3) 0.0336(11) Uani 1 1 d . . . C34 C 0.5747(3) 0.7124(3) 0.5379(3) 0.0426(13) Uani 1 1 d . . . H34A H 0.5777 0.7472 0.5757 0.051 Uiso 1 1 calc R . . C35 C 0.5236(3) 0.7101(3) 0.4871(4) 0.0529(16) Uani 1 1 d . . . H35A H 0.4919 0.7438 0.4883 0.064 Uiso 1 1 calc R . . C36 C 0.5189(3) 0.6580(3) 0.4341(4) 0.0499(15) Uani 1 1 d . . . H36A H 0.4839 0.6553 0.3985 0.060 Uiso 1 1 calc R . . C37 C 0.5656(3) 0.6100(3) 0.4339(3) 0.0405(13) Uani 1 1 d . . . H37A H 0.5618 0.5737 0.3984 0.049 Uiso 1 1 calc R . . N5 N 0.6168(2) 0.6127(2) 0.4822(2) 0.0317(9) Uani 1 1 d . . . P1 P 0.5000 0.7894(2) 0.2500 0.1003(13) Uani 1 2 d SDU . . F10 F 0.5506(4) 0.7270(7) 0.2664(15) 0.199(11) Uani 0.50 1 d PDU A 1 F11 F 0.5427(5) 0.8359(9) 0.2891(8) 0.197(13) Uani 0.50 1 d PDU A 1 F12 F 0.5325(10) 0.7955(10) 0.1688(7) 0.118(7) Uani 0.50 1 d PD A 1 F10' F 0.5487(11) 0.7480(10) 0.2796(13) 0.202(11) Uani 0.50 1 d PDU A 2 F11' F 0.5529(8) 0.8513(8) 0.2493(12) 0.136(7) Uani 0.50 1 d PD A 2 F12' F 0.5227(19) 0.7802(16) 0.1611(10) 0.214(15) Uani 0.50 1 d PDU A 2 P2 P 0.5000 0.79701(10) 0.7500 0.0345(4) Uani 1 2 d S . . F20 F 0.5000 0.8741(3) 0.7500 0.105(3) Uani 1 2 d S . . F21 F 0.5244(2) 0.7968(3) 0.8382(2) 0.0759(14) Uani 1 1 d . . . F22 F 0.57171(19) 0.7963(3) 0.7216(3) 0.0864(17) Uani 1 1 d . . . F23 F 0.5000 0.7186(3) 0.7500 0.106(3) Uani 1 2 d S . . C100 C 1.00529(14) 0.4965(3) 0.4398(4) 0.072(5) Uani 0.50 1 d PR . . C101 C 0.97741(14) 0.5539(3) 0.4698(4) 0.087(9) Uani 0.50 1 d PR . . H101 H 0.9627 0.5875 0.4348 0.105 Uiso 0.50 1 calc PR . . C102 C 0.97106(10) 0.5623(3) 0.5512(4) 0.135(15) Uani 0.50 1 d PR . . H102 H 0.9520 0.6015 0.5716 0.162 Uiso 0.50 1 calc PR . . C103 C 0.99257(8) 0.5132(3) 0.6025(4) 0.088(7) Uani 0.50 1 d PRU . . H103 H 0.9882 0.5189 0.6580 0.106 Uiso 0.50 1 calc PR . . C104 C 1.02048(9) 0.4558(3) 0.5725(4) 0.125(12) Uani 0.50 1 d PRU . . H104 H 1.0352 0.4223 0.6075 0.150 Uiso 0.50 1 calc PR . . C105 C 1.02682(12) 0.4475(3) 0.4911(4) 0.100(11) Uani 0.50 1 d PR . . H105 H 1.0459 0.4082 0.4707 0.120 Uiso 0.50 1 calc PR . . C106 C 1.00776(17) 0.4875(3) 0.3508(3) 0.066(5) Uani 0.50 1 d PR . . H10A H 1.0482 0.5052 0.3305 0.099 Uiso 0.50 1 calc PR . . H10B H 0.9720 0.5113 0.3264 0.099 Uiso 0.50 1 calc PR . . H10C H 1.0047 0.4401 0.3380 0.099 Uiso 0.50 1 calc PR . . 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 0.02937(10) 0.03399(11) 0.02175(10) -0.00123(7) 0.00474(7) -0.01060(8) N1 0.031(2) 0.030(2) 0.030(2) -0.0041(17) 0.0036(17) -0.0080(18) N2 0.028(2) 0.036(2) 0.0222(19) 0.0001(17) 0.0059(16) -0.0040(18) C1 0.034(3) 0.041(3) 0.037(3) -0.003(2) 0.008(2) -0.012(2) C2 0.038(3) 0.046(3) 0.042(3) -0.005(3) 0.002(2) -0.017(3) C3 0.041(3) 0.047(3) 0.039(3) -0.012(3) -0.003(2) -0.013(3) C4 0.035(3) 0.040(3) 0.028(2) -0.003(2) 0.004(2) -0.007(2) C5 0.031(2) 0.032(3) 0.029(2) -0.0008(19) 0.002(2) -0.002(2) C6 0.032(3) 0.036(3) 0.024(2) -0.001(2) 0.0037(19) -0.003(2) C7 0.039(3) 0.048(3) 0.033(3) -0.007(2) 0.010(2) -0.003(3) C8 0.036(3) 0.063(4) 0.042(3) -0.006(3) 0.017(2) -0.009(3) C9 0.035(3) 0.053(4) 0.044(3) -0.001(3) 0.011(2) -0.017(3) C10 0.035(3) 0.039(3) 0.030(3) 0.001(2) 0.009(2) -0.009(2) C11 0.047(3) 0.042(3) 0.039(3) 0.001(2) 0.017(3) -0.018(3) C12 0.061(4) 0.044(4) 0.052(4) 0.011(3) 0.026(3) 0.005(3) C13 0.093(7) 0.044(4) 0.087(6) 0.007(4) 0.050(5) 0.003(4) C14 0.090(6) 0.042(4) 0.103(6) -0.030(4) 0.049(5) -0.025(4) N3 0.060(4) 0.061(4) 0.068(4) -0.019(3) 0.030(3) -0.030(3) C15 0.059(5) 0.105(7) 0.063(5) -0.022(5) 0.013(4) -0.042(5) C16 0.051(3) 0.037(3) 0.025(2) -0.004(2) 0.007(2) -0.024(3) C17 0.050(4) 0.069(4) 0.031(3) -0.006(3) 0.011(3) -0.032(3) C18 0.073(5) 0.092(6) 0.034(3) -0.001(4) 0.016(3) -0.044(5) C19 0.090(6) 0.095(6) 0.029(3) 0.004(4) 0.014(3) -0.058(5) C20 0.104(6) 0.051(4) 0.034(3) 0.008(3) -0.007(4) -0.038(4) C21 0.068(4) 0.038(3) 0.028(3) 0.000(2) 0.004(3) -0.027(3) C22 0.070(4) 0.029(3) 0.036(3) 0.001(2) -0.009(3) -0.011(3) C23 0.093(6) 0.039(4) 0.061(4) 0.009(3) -0.008(4) 0.003(4) C24 0.094(7) 0.042(4) 0.088(6) 0.008(4) -0.024(5) 0.019(4) C25 0.052(4) 0.053(4) 0.074(5) -0.002(4) -0.011(4) 0.009(3) C26 0.045(3) 0.045(3) 0.045(3) 0.004(2) -0.002(3) -0.002(3) N4 0.043(2) 0.035(2) 0.030(2) 0.0005(18) -0.0019(19) -0.0085(19) C27 0.033(3) 0.035(3) 0.024(2) 0.0025(19) 0.0046(19) -0.016(2) C28 0.041(3) 0.043(3) 0.032(3) 0.004(2) 0.000(2) -0.015(3) C29 0.051(4) 0.051(4) 0.040(3) 0.003(3) -0.012(3) -0.021(3) C30 0.077(5) 0.038(3) 0.040(3) -0.002(3) -0.014(3) -0.022(3) C31 0.062(4) 0.039(3) 0.033(3) -0.002(2) -0.003(3) -0.013(3) C32 0.039(3) 0.036(3) 0.026(2) 0.001(2) 0.005(2) -0.014(2) C33 0.032(3) 0.040(3) 0.028(2) -0.003(2) 0.010(2) -0.009(2) C34 0.040(3) 0.044(3) 0.044(3) -0.010(3) 0.011(2) -0.006(3) C35 0.039(3) 0.054(4) 0.066(4) -0.010(3) 0.006(3) 0.008(3) C36 0.032(3) 0.063(4) 0.055(4) -0.011(3) -0.002(3) 0.000(3) C37 0.029(3) 0.054(4) 0.038(3) -0.010(3) 0.001(2) -0.004(2) N5 0.027(2) 0.039(2) 0.028(2) -0.0041(18) 0.0086(17) -0.0066(18) P1 0.124(4) 0.071(2) 0.105(3) 0.000 -0.032(3) 0.000 F10 0.32(3) 0.117(12) 0.156(16) -0.013(12) 0.048(18) 0.145(14) F11 0.084(11) 0.31(3) 0.20(2) -0.14(2) 0.032(13) -0.067(15) F12 0.131(12) 0.148(17) 0.076(9) 0.023(9) 0.010(8) -0.083(12) F10' 0.26(2) 0.197(18) 0.148(17) 0.063(14) 0.077(14) 0.198(16) F11' 0.104(12) 0.115(11) 0.188(16) -0.067(11) 0.067(11) -0.036(9) F12' 0.36(4) 0.145(18) 0.135(17) -0.042(14) -0.02(2) -0.12(2) P2 0.0302(10) 0.0335(10) 0.0398(10) 0.000 -0.0040(8) 0.000 F20 0.181(9) 0.036(3) 0.097(5) 0.000 -0.010(5) 0.000 F21 0.063(3) 0.121(4) 0.044(2) 0.016(2) -0.0161(19) -0.007(3) F22 0.037(2) 0.152(5) 0.069(3) -0.037(3) 0.005(2) -0.026(3) F23 0.065(4) 0.038(3) 0.216(9) 0.000 -0.067(5) 0.000 C100 0.072(11) 0.071(11) 0.071(12) -0.027(10) -0.007(10) -0.022(9) C101 0.031(9) 0.057(13) 0.17(3) 0.034(12) -0.037(10) 0.001(8) C102 0.055(12) 0.24(3) 0.12(2) -0.11(2) 0.024(13) -0.057(17) C103 0.080(13) 0.121(17) 0.064(12) 0.001(12) -0.043(11) -0.026(12) C104 0.101(18) 0.092(17) 0.18(3) 0.046(16) -0.051(16) -0.019(14) C105 0.078(16) 0.072(15) 0.15(3) 0.066(16) -0.048(15) -0.009(12) C106 0.080(11) 0.086(12) 0.031(7) -0.002(7) -0.005(7) -0.023(9) _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 C16 1.990(5) . ? Ir1 C27 2.012(5) . ? Ir1 N5 2.034(4) . ? Ir1 N4 2.037(5) . ? Ir1 N1 2.144(4) . ? Ir1 N2 2.193(4) . ? N1 C1 1.336(6) . ? N1 C5 1.355(6) . ? N2 C10 1.350(7) . ? N2 C6 1.358(6) . ? C1 C2 1.379(8) . ? C1 H1A 0.9500 . ? C2 C3 1.384(8) . ? C2 H2A 0.9500 . ? C3 C4 1.379(7) . ? C3 H3A 0.9500 . ? C4 C5 1.386(7) . ? C4 H4A 0.9500 . ? C5 C6 1.472(7) . ? C6 C7 1.391(7) . ? C7 C8 1.393(8) . ? C7 H7A 0.9500 . ? C8 C9 1.373(9) . ? C8 H8A 0.9500 . ? C9 C10 1.407(7) . ? C9 H9A 0.9500 . ? C10 C11 1.467(8) . ? C11 N3 1.353(8) . ? C11 C12 1.399(9) . ? C12 C13 1.391(10) . ? C12 H12A 0.9500 . ? C13 C14 1.355(13) . ? C13 H13A 0.9500 . ? C14 N3 1.369(10) . ? C14 H14A 0.9500 . ? N3 C15 1.442(11) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.398(9) . ? C16 C21 1.399(9) . ? C17 C18 1.384(8) . ? C17 H17A 0.9500 . ? C18 C19 1.374(12) . ? C18 H18A 0.9500 . ? C19 C20 1.381(12) . ? C19 H19A 0.9500 . ? C20 C21 1.425(8) . ? C20 H20A 0.9500 . ? C21 C22 1.456(9) . ? C22 N4 1.375(7) . ? C22 C23 1.389(10) . ? C23 C24 1.361(12) . ? C23 H23A 0.9500 . ? C24 C25 1.378(11) . ? C24 H24A 0.9500 . ? C25 C26 1.371(9) . ? C25 H25A 0.9500 . ? C26 N4 1.346(8) . ? C26 H26A 0.9500 . ? C27 C32 1.402(8) . ? C27 C28 1.412(8) . ? C28 C29 1.386(8) . ? C28 H28A 0.9500 . ? C29 C30 1.381(10) . ? C29 H29A 0.9500 . ? C30 C31 1.387(9) . ? C30 H30A 0.9500 . ? C31 C32 1.398(7) . ? C31 H31A 0.9500 . ? C32 C33 1.464(8) . ? C33 N5 1.366(7) . ? C33 C34 1.383(8) . ? C34 C35 1.374(9) . ? C34 H34A 0.9500 . ? C35 C36 1.383(9) . ? C35 H35A 0.9500 . ? C36 C37 1.375(9) . ? C36 H36A 0.9500 . ? C37 N5 1.348(7) . ? C37 H37A 0.9500 . ? P1 F10' 1.409(18) 3_655 ? P1 F10' 1.409(18) . ? P1 F11 1.453(11) . ? P1 F11 1.453(11) 3_655 ? P1 F12 1.538(12) . ? P1 F12 1.538(12) 3_655 ? P1 F12' 1.589(10) . ? P1 F12' 1.589(10) 3_655 ? P1 F10 1.667(11) 3_655 ? P1 F10 1.667(11) . ? P1 F11' 1.667(16) . ? P1 F11' 1.667(16) 3_655 ? P2 F20 1.551(7) . ? P2 F21 1.576(4) 3_656 ? P2 F21 1.576(4) . ? P2 F22 1.577(4) 3_656 ? P2 F22 1.577(4) . ? P2 F23 1.579(5) . ? C100 C105 1.3898 . ? C100 C101 1.3905 . ? C100 C106 1.5185 . ? C101 C102 1.3927 . ? C101 H101 0.9500 . ? C102 C103 1.3894 . ? C102 H102 0.9500 . ? C103 C104 1.3907 . ? C103 H103 0.9500 . ? C104 C105 1.3921 . ? C104 H104 0.9500 . ? C105 H105 0.9500 . ? C106 H10A 0.9800 . ? C106 H10B 0.9800 . ? C106 H10C 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 C16 Ir1 C27 87.6(2) . . ? C16 Ir1 N5 92.4(2) . . ? C27 Ir1 N5 80.4(2) . . ? C16 Ir1 N4 80.6(2) . . ? C27 Ir1 N4 92.3(2) . . ? N5 Ir1 N4 170.13(17) . . ? C16 Ir1 N1 94.28(18) . . ? C27 Ir1 N1 178.17(17) . . ? N5 Ir1 N1 99.41(17) . . ? N4 Ir1 N1 88.14(17) . . ? C16 Ir1 N2 167.6(2) . . ? C27 Ir1 N2 102.64(17) . . ? N5 Ir1 N2 96.24(16) . . ? N4 Ir1 N2 91.77(17) . . ? N1 Ir1 N2 75.55(16) . . ? C1 N1 C5 118.6(4) . . ? C1 N1 Ir1 126.4(4) . . ? C5 N1 Ir1 114.7(3) . . ? C10 N2 C6 119.5(4) . . ? C10 N2 Ir1 126.2(3) . . ? C6 N2 Ir1 109.9(3) . . ? N1 C1 C2 122.8(5) . . ? N1 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? C1 C2 C3 118.6(5) . . ? C1 C2 H2A 120.7 . . ? C3 C2 H2A 120.7 . . ? C4 C3 C2 119.3(5) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 119.2(5) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? N1 C5 C4 121.5(5) . . ? N1 C5 C6 115.0(4) . . ? C4 C5 C6 123.4(4) . . ? N2 C6 C7 121.8(5) . . ? N2 C6 C5 115.6(4) . . ? C7 C6 C5 122.6(5) . . ? C6 C7 C8 118.0(5) . . ? C6 C7 H7A 121.0 . . ? C8 C7 H7A 121.0 . . ? C9 C8 C7 119.8(5) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? C8 C9 C10 119.6(5) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? N2 C10 C9 119.9(5) . . ? N2 C10 C11 117.0(5) . . ? C9 C10 C11 122.6(5) . . ? N3 C11 C12 107.9(6) . . ? N3 C11 C10 125.7(6) . . ? C12 C11 C10 124.9(6) . . ? C13 C12 C11 106.9(7) . . ? C13 C12 H12A 126.5 . . ? C11 C12 H12A 126.5 . . ? C14 C13 C12 107.5(8) . . ? C14 C13 H13A 126.3 . . ? C12 C13 H13A 126.3 . . ? C13 C14 N3 109.3(7) . . ? C13 C14 H14A 125.3 . . ? N3 C14 H14A 125.3 . . ? C11 N3 C14 108.3(7) . . ? C11 N3 C15 126.4(7) . . ? C14 N3 C15 124.7(7) . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 117.2(5) . . ? C17 C16 Ir1 127.5(5) . . ? C21 C16 Ir1 115.0(4) . . ? C18 C17 C16 121.5(7) . . ? C18 C17 H17A 119.2 . . ? C16 C17 H17A 119.2 . . ? C19 C18 C17 120.7(8) . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C18 C19 C20 120.6(6) . . ? C18 C19 H19A 119.7 . . ? C20 C19 H19A 119.7 . . ? C19 C20 C21 118.5(8) . . ? C19 C20 H20A 120.7 . . ? C21 C20 H20A 120.7 . . ? C16 C21 C20 121.5(7) . . ? C16 C21 C22 115.0(5) . . ? C20 C21 C22 123.5(7) . . ? N4 C22 C23 119.6(7) . . ? N4 C22 C21 113.9(5) . . ? C23 C22 C21 126.4(6) . . ? C24 C23 C22 120.9(7) . . ? C24 C23 H23A 119.6 . . ? C22 C23 H23A 119.6 . . ? C23 C24 C25 119.4(7) . . ? C23 C24 H24A 120.3 . . ? C25 C24 H24A 120.3 . . ? C26 C25 C24 118.6(7) . . ? C26 C25 H25A 120.7 . . ? C24 C25 H25A 120.7 . . ? N4 C26 C25 123.1(6) . . ? N4 C26 H26A 118.4 . . ? C25 C26 H26A 118.4 . . ? C26 N4 C22 118.4(5) . . ? C26 N4 Ir1 126.3(4) . . ? C22 N4 Ir1 115.1(4) . . ? C32 C27 C28 117.4(5) . . ? C32 C27 Ir1 114.0(4) . . ? C28 C27 Ir1 128.5(4) . . ? C29 C28 C27 120.8(6) . . ? C29 C28 H28A 119.6 . . ? C27 C28 H28A 119.6 . . ? C30 C29 C28 120.7(6) . . ? C30 C29 H29A 119.7 . . ? C28 C29 H29A 119.7 . . ? C29 C30 C31 120.0(6) . . ? C29 C30 H30A 120.0 . . ? C31 C30 H30A 120.0 . . ? C30 C31 C32 119.6(6) . . ? C30 C31 H31A 120.2 . . ? C32 C31 H31A 120.2 . . ? C31 C32 C27 121.4(5) . . ? C31 C32 C33 123.1(5) . . ? C27 C32 C33 115.5(5) . . ? N5 C33 C34 120.4(5) . . ? N5 C33 C32 113.5(5) . . ? C34 C33 C32 126.1(5) . . ? C35 C34 C33 120.3(6) . . ? C35 C34 H34A 119.9 . . ? C33 C34 H34A 119.9 . . ? C34 C35 C36 119.1(6) . . ? C34 C35 H35A 120.4 . . ? C36 C35 H35A 120.4 . . ? C37 C36 C35 118.9(6) . . ? C37 C36 H36A 120.5 . . ? C35 C36 H36A 120.5 . . ? N5 C37 C36 122.4(5) . . ? N5 C37 H37A 118.8 . . ? C36 C37 H37A 118.8 . . ? C37 N5 C33 118.8(5) . . ? C37 N5 Ir1 125.2(4) . . ? C33 N5 Ir1 115.9(4) . . ? F10' P1 F10' 107(2) 3_655 . ? F10' P1 F11 171.0(13) 3_655 . ? F10' P1 F11 77.0(10) . . ? F10' P1 F11 77.0(10) 3_655 3_655 ? F10' P1 F11 171.0(13) . 3_655 ? F11 P1 F11 99.8(11) . 3_655 ? F10' P1 F12 92.9(11) 3_655 . ? F10' P1 F12 92.5(16) . . ? F11 P1 F12 94.7(8) . . ? F11 P1 F12 79.3(13) 3_655 . ? F10' P1 F12 92.5(16) 3_655 3_655 ? F10' P1 F12 92.9(11) . 3_655 ? F11 P1 F12 79.3(13) . 3_655 ? F11 P1 F12 94.7(8) 3_655 3_655 ? F12 P1 F12 170.8(16) . 3_655 ? F10' P1 F12' 79.1(11) 3_655 . ? F10' P1 F12' 92.9(18) . . ? F11 P1 F12' 108.8(9) . . ? F11 P1 F12' 80.1(18) 3_655 . ? F12 P1 F12' 14.3(7) . . ? F12 P1 F12' 171(2) 3_655 . ? F10' P1 F12' 92.9(18) 3_655 3_655 ? F10' P1 F12' 79.1(11) . 3_655 ? F11 P1 F12' 80.1(18) . 3_655 ? F11 P1 F12' 108.8(9) 3_655 3_655 ? F12 P1 F12' 171(2) . 3_655 ? F12 P1 F12' 14.3(7) 3_655 3_655 ? F12' P1 F12' 167(2) . 3_655 ? F10' P1 F10 15.1(9) 3_655 3_655 ? F10' P1 F10 94.2(11) . 3_655 ? F11 P1 F10 162.2(11) . 3_655 ? F11 P1 F10 91.0(5) 3_655 3_655 ? F12 P1 F10 101.2(10) . 3_655 ? F12 P1 F10 85.8(9) 3_655 3_655 ? F12' P1 F10 86.9(11) . 3_655 ? F12' P1 F10 83(2) 3_655 3_655 ? F10' P1 F10 94.2(11) 3_655 . ? F10' P1 F10 15.1(9) . . ? F11 P1 F10 91.0(5) . . ? F11 P1 F10 162.2(11) 3_655 . ? F12 P1 F10 85.8(9) . . ? F12 P1 F10 101.2(10) 3_655 . ? F12' P1 F10 83(2) . . ? F12' P1 F10 86.9(11) 3_655 . ? F10 P1 F10 82.3(7) 3_655 . ? F10' P1 F11' 157.0(11) 3_655 . ? F10' P1 F11' 87.9(13) . . ? F11 P1 F11' 27.5(6) . . ? F11 P1 F11' 85.6(9) 3_655 . ? F12 P1 F11' 68.9(7) . . ? F12 P1 F11' 103.9(12) 3_655 . ? F12' P1 F11' 83.2(8) . . ? F12' P1 F11' 107.0(18) 3_655 . ? F10 P1 F11' 169.9(11) 3_655 . ? F10 P1 F11' 98.1(8) . . ? F10' P1 F11' 87.9(13) 3_655 3_655 ? F10' P1 F11' 157.0(11) . 3_655 ? F11 P1 F11' 85.6(9) . 3_655 ? F11 P1 F11' 27.5(6) 3_655 3_655 ? F12 P1 F11' 103.9(12) . 3_655 ? F12 P1 F11' 68.9(7) 3_655 3_655 ? F12' P1 F11' 107.0(18) . 3_655 ? F12' P1 F11' 83.2(8) 3_655 3_655 ? F10 P1 F11' 98.1(8) 3_655 3_655 ? F10 P1 F11' 169.9(11) . 3_655 ? F11' P1 F11' 83.3(13) . 3_655 ? F20 P2 F21 90.2(2) . 3_656 ? F20 P2 F21 90.2(2) . . ? F21 P2 F21 179.6(4) 3_656 . ? F20 P2 F22 90.5(2) . 3_656 ? F21 P2 F22 88.8(2) 3_656 3_656 ? F21 P2 F22 91.2(2) . 3_656 ? F20 P2 F22 90.5(2) . . ? F21 P2 F22 91.2(2) 3_656 . ? F21 P2 F22 88.8(2) . . ? F22 P2 F22 179.0(5) 3_656 . ? F20 P2 F23 180.000(2) . . ? F21 P2 F23 89.8(2) 3_656 . ? F21 P2 F23 89.8(2) . . ? F22 P2 F23 89.5(2) 3_656 . ? F22 P2 F23 89.5(2) . . ? C105 C100 C101 119.9 . . ? C105 C100 C106 121.6 . . ? C101 C100 C106 118.4 . . ? C100 C101 C102 120.1 . . ? C100 C101 H101 120.0 . . ? C102 C101 H101 120.0 . . ? C103 C102 C101 120.0 . . ? C103 C102 H102 120.0 . . ? C101 C102 H102 120.0 . . ? C102 C103 C104 119.9 . . ? C102 C103 H103 120.1 . . ? C104 C103 H103 120.1 . . ? C103 C104 C105 120.1 . . ? C103 C104 H104 120.0 . . ? C105 C104 H104 120.0 . . ? C100 C105 C104 120.0 . . ? C100 C105 H105 120.0 . . ? C104 C105 H105 120.0 . . ? C100 C106 H10A 109.5 . . ? C100 C106 H10B 109.5 . . ? H10A C106 H10B 109.5 . . ? C100 C106 H10C 109.5 . . ? H10A C106 H10C 109.5 . . ? H10B C106 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.387 _refine_diff_density_min -1.912 _refine_diff_density_rms 0.105 data_pka249 _database_code_depnum_ccdc_archive 'CCDC 925642' #TrackingRef 'PKA249revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H44 Ir N4 O6, F6 P' _chemical_formula_sum 'C50 H44 F6 Ir N4 O6 P' _chemical_formula_weight 1134.08 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.5203(8) _cell_length_b 18.8096(10) _cell_length_c 18.9682(13) _cell_angle_alpha 90.00 _cell_angle_beta 95.328(5) _cell_angle_gamma 90.00 _cell_volume 4447.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 21728 _cell_measurement_theta_min 4.18 _cell_measurement_theta_max 56.73 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2264 _exptl_absorpt_coefficient_mu 3.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3341 _exptl_absorpt_correction_T_max 0.6518 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 77004 _diffrn_reflns_av_R_equivalents 0.0874 _diffrn_reflns_av_unetI/netI 0.0349 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.50 _reflns_number_total 10213 _reflns_number_gt 9844 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _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^)+(0.0348P)^2^+11.4002P] 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_number_reflns 10213 _refine_ls_number_parameters 619 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 0.926714(10) 0.269051(7) 0.086371(7) 0.02852(6) Uani 1 1 d . . . N1 N 1.0277(2) 0.17799(17) 0.08257(17) 0.0316(6) Uani 1 1 d . . . N2 N 0.8291(2) 0.19020(16) 0.02314(15) 0.0272(6) Uani 1 1 d . . . C1 C 1.1326(3) 0.1761(2) 0.1072(2) 0.0376(9) Uani 1 1 d . . . H1A H 1.1703 0.2196 0.1149 0.045 Uiso 1 1 calc R . . C2 C 1.1863(3) 0.1135(3) 0.1214(2) 0.0421(10) Uani 1 1 d . . . H2A H 1.2605 0.1138 0.1373 0.051 Uiso 1 1 calc R . . C3 C 1.1316(3) 0.0501(3) 0.1125(2) 0.0418(9) Uani 1 1 d . . . H3A H 1.1662 0.0064 0.1253 0.050 Uiso 1 1 calc R . . C4 C 1.0253(3) 0.0512(2) 0.0846(2) 0.0377(8) Uani 1 1 d . . . H4A H 0.9869 0.0080 0.0761 0.045 Uiso 1 1 calc R . . C5 C 0.9759(3) 0.1158(2) 0.0693(2) 0.0309(7) Uani 1 1 d . . . C6 C 0.8647(3) 0.12257(19) 0.03593(19) 0.0284(7) Uani 1 1 d . . . C7 C 0.8030(3) 0.0634(2) 0.0164(2) 0.0301(7) Uani 1 1 d . . . H7A H 0.8304 0.0172 0.0272 0.036 Uiso 1 1 calc R . . C8 C 0.7005(3) 0.07113(19) -0.0191(2) 0.0295(7) Uani 1 1 d . . . C9 C 0.6675(3) 0.14033(19) -0.03379(19) 0.0290(7) Uani 1 1 d . . . H9A H 0.5986 0.1485 -0.0579 0.035 Uiso 1 1 calc R . . C10 C 0.7327(3) 0.19793(19) -0.01403(18) 0.0278(7) Uani 1 1 d . . . C11 C 0.6986(3) 0.26967(18) -0.0408(2) 0.0306(8) Uani 1 1 d . . . C12 C 0.6102(3) 0.3034(2) -0.0166(2) 0.0326(7) Uani 1 1 d . . . H12A H 0.5723 0.2823 0.0192 0.039 Uiso 1 1 calc R . . C13 C 0.5784(3) 0.3689(2) -0.0462(2) 0.0377(9) Uani 1 1 d . . . C14 C 0.6322(4) 0.3988(2) -0.0998(2) 0.0400(9) Uani 1 1 d . . . C15 C 0.7184(4) 0.3628(2) -0.1250(2) 0.0398(9) Uani 1 1 d . . . C16 C 0.7522(3) 0.2979(2) -0.0952(2) 0.0348(8) Uani 1 1 d . . . H16A H 0.8112 0.2734 -0.1119 0.042 Uiso 1 1 calc R . . C17 C 0.4439(4) 0.3839(3) 0.0340(3) 0.0537(12) Uani 1 1 d . . . H17A H 0.4071 0.3386 0.0234 0.080 Uiso 1 1 calc R . . H17B H 0.3918 0.4196 0.0463 0.080 Uiso 1 1 calc R . . H17C H 0.4986 0.3774 0.0739 0.080 Uiso 1 1 calc R . . C18 C 0.5570(5) 0.4718(3) -0.1933(3) 0.0621(14) Uani 1 1 d . . . H18A H 0.6004 0.4469 -0.2259 0.093 Uiso 1 1 calc R . . H18B H 0.5508 0.5221 -0.2067 0.093 Uiso 1 1 calc R . . H18C H 0.4853 0.4505 -0.1958 0.093 Uiso 1 1 calc R . . C19 C 0.8379(4) 0.3548(3) -0.2148(3) 0.0582(13) Uani 1 1 d . . . H19A H 0.8974 0.3377 -0.1819 0.087 Uiso 1 1 calc R . . H19B H 0.8662 0.3839 -0.2517 0.087 Uiso 1 1 calc R . . H19C H 0.7989 0.3140 -0.2368 0.087 Uiso 1 1 calc R . . C20 C 0.6341(3) 0.00936(19) -0.0432(2) 0.0297(7) Uani 1 1 d . . . C21 C 0.6439(3) -0.0548(2) -0.0065(2) 0.0336(8) Uani 1 1 d . . . H21A H 0.6918 -0.0587 0.0352 0.040 Uiso 1 1 calc R . . C22 C 0.5832(3) -0.1133(2) -0.0311(2) 0.0339(8) Uani 1 1 d . . . C23 C 0.5099(3) -0.1072(2) -0.0913(2) 0.0340(8) Uani 1 1 d . . . C24 C 0.5009(3) -0.0433(2) -0.1275(2) 0.0354(8) Uani 1 1 d . . . C25 C 0.5631(3) 0.0148(2) -0.1042(2) 0.0339(8) Uani 1 1 d . . . H25A H 0.5574 0.0582 -0.1298 0.041 Uiso 1 1 calc R . . C26 C 0.6709(4) -0.1887(3) 0.0557(3) 0.0544(12) Uani 1 1 d . . . H26A H 0.7403 -0.1767 0.0388 0.082 Uiso 1 1 calc R . . H26B H 0.6715 -0.2386 0.0707 0.082 Uiso 1 1 calc R . . H26C H 0.6580 -0.1582 0.0958 0.082 Uiso 1 1 calc R . . C27 C 0.4853(4) -0.2116(3) -0.1607(3) 0.0548(12) Uani 1 1 d . . . H27A H 0.4887 -0.1875 -0.2062 0.082 Uiso 1 1 calc R . . H27B H 0.4377 -0.2529 -0.1671 0.082 Uiso 1 1 calc R . . H27C H 0.5573 -0.2273 -0.1426 0.082 Uiso 1 1 calc R . . C28 C 0.4113(5) 0.0236(3) -0.2221(3) 0.0617(14) Uani 1 1 d . . . H28A H 0.3886 0.0594 -0.1890 0.093 Uiso 1 1 calc R . . H28B H 0.3554 0.0179 -0.2614 0.093 Uiso 1 1 calc R . . H28C H 0.4780 0.0392 -0.2406 0.093 Uiso 1 1 calc R . . O1 O 0.4937(3) 0.40706(19) -0.02646(18) 0.0526(8) Uani 1 1 d . . . O2 O 0.6065(3) 0.46605(18) -0.1236(2) 0.0618(10) Uani 1 1 d . . . O3 O 0.7668(3) 0.39644(19) -0.17712(19) 0.0521(8) Uani 1 1 d . . . O4 O 0.5881(2) -0.17820(16) 0.00006(18) 0.0455(7) Uani 1 1 d . . . O5 O 0.4449(2) -0.16385(15) -0.11151(17) 0.0412(7) Uani 1 1 d . . . O6 O 0.4287(2) -0.04255(17) -0.18625(18) 0.0479(8) Uani 1 1 d . . . N3 N 0.8858(3) 0.22549(16) 0.17937(18) 0.0316(7) Uani 1 1 d . . . C29 C 0.8036(3) 0.1816(2) 0.1867(2) 0.0377(8) Uani 1 1 d . . . H29A H 0.7561 0.1710 0.1461 0.045 Uiso 1 1 calc R . . C30 C 0.7844(4) 0.1509(3) 0.2506(3) 0.0459(10) Uani 1 1 d . . . H30A H 0.7248 0.1204 0.2542 0.055 Uiso 1 1 calc R . . C31 C 0.8555(4) 0.1665(3) 0.3091(3) 0.0507(11) Uani 1 1 d . . . H31A H 0.8464 0.1454 0.3537 0.061 Uiso 1 1 calc R . . C32 C 0.9395(4) 0.2128(3) 0.3025(2) 0.0461(10) Uani 1 1 d . . . H32A H 0.9876 0.2240 0.3427 0.055 Uiso 1 1 calc R . . C33 C 0.9539(3) 0.2430(2) 0.2375(2) 0.0365(8) Uani 1 1 d . . . C34 C 1.0360(3) 0.2947(2) 0.2241(2) 0.0368(8) Uani 1 1 d . . . C35 C 1.0329(3) 0.3205(2) 0.1543(2) 0.0366(8) Uani 1 1 d . . . C36 C 1.1075(3) 0.3718(3) 0.1387(3) 0.0467(10) Uani 1 1 d . . . H36A H 1.1052 0.3909 0.0922 0.056 Uiso 1 1 calc R . . C37 C 1.1854(4) 0.3953(3) 0.1907(3) 0.0583(13) Uani 1 1 d . . . H37A H 1.2356 0.4305 0.1796 0.070 Uiso 1 1 calc R . . C38 C 1.1899(4) 0.3677(3) 0.2584(3) 0.0590(14) Uani 1 1 d . . . H38A H 1.2443 0.3831 0.2934 0.071 Uiso 1 1 calc R . . C39 C 1.1157(4) 0.3180(3) 0.2754(3) 0.0494(11) Uani 1 1 d . . . H39A H 1.1187 0.2995 0.3222 0.059 Uiso 1 1 calc R . . N4 N 0.9715(3) 0.32646(18) 0.00233(18) 0.0358(7) Uani 1 1 d . . . C40 C 1.0496(3) 0.3061(3) -0.0378(2) 0.0445(10) Uani 1 1 d . . . H40A H 1.0805 0.2602 -0.0306 0.053 Uiso 1 1 calc R . . C41 C 1.0860(4) 0.3499(4) -0.0893(3) 0.0599(14) Uani 1 1 d . . . H41A H 1.1411 0.3347 -0.1170 0.072 Uiso 1 1 calc R . . C42 C 1.0395(5) 0.4169(3) -0.0991(3) 0.0610(14) Uani 1 1 d . . . H42A H 1.0643 0.4487 -0.1328 0.073 Uiso 1 1 calc R . . C43 C 0.9572(5) 0.4370(3) -0.0596(3) 0.0535(12) Uani 1 1 d . . . H43A H 0.9233 0.4819 -0.0677 0.064 Uiso 1 1 calc R . . C44 C 0.9236(4) 0.3911(2) -0.0075(2) 0.0410(9) Uani 1 1 d . . . C45 C 0.8424(3) 0.4059(2) 0.0403(2) 0.0383(9) Uani 1 1 d . . . C46 C 0.8297(3) 0.35384(19) 0.0915(2) 0.0323(8) Uani 1 1 d . . . C47 C 0.7558(3) 0.3670(2) 0.1411(2) 0.0402(9) Uani 1 1 d . . . H47A H 0.7474 0.3335 0.1777 0.048 Uiso 1 1 calc R . . C48 C 0.6945(4) 0.4291(3) 0.1370(3) 0.0487(11) Uani 1 1 d . . . H48A H 0.6447 0.4374 0.1709 0.058 Uiso 1 1 calc R . . C49 C 0.7052(4) 0.4782(3) 0.0849(3) 0.0540(12) Uani 1 1 d . . . H49A H 0.6622 0.5198 0.0824 0.065 Uiso 1 1 calc R . . C50 C 0.7780(4) 0.4672(2) 0.0365(3) 0.0488(11) Uani 1 1 d . . . H50A H 0.7849 0.5011 0.0001 0.059 Uiso 1 1 calc R . . P1 P 1.04465(12) 0.14022(7) -0.16801(7) 0.0534(3) Uani 1 1 d . . . F10 F 0.9463(3) 0.0873(2) -0.1670(2) 0.0841(11) Uani 1 1 d . . . F11 F 1.0244(4) 0.1456(2) -0.2515(2) 0.1028(15) Uani 1 1 d . . . F12 F 1.1200(4) 0.0747(3) -0.1750(3) 0.1111(16) Uani 1 1 d . . . F13 F 1.0671(3) 0.1319(3) -0.08461(18) 0.0932(14) Uani 1 1 d . . . F14 F 0.9670(4) 0.2050(2) -0.1619(3) 0.1076(16) Uani 1 1 d . . . F15 F 1.1400(4) 0.1947(3) -0.1670(3) 0.1139(18) 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 0.02634(8) 0.02922(9) 0.02865(9) -0.00286(5) -0.00461(5) -0.00358(5) N1 0.0277(14) 0.0343(16) 0.0318(16) -0.0040(13) -0.0025(12) -0.0019(12) N2 0.0285(14) 0.0264(14) 0.0253(14) -0.0019(11) -0.0050(11) -0.0035(11) C1 0.0251(17) 0.048(2) 0.039(2) -0.0073(18) -0.0017(15) -0.0013(16) C2 0.0260(17) 0.057(3) 0.042(2) -0.008(2) -0.0030(15) 0.0053(17) C3 0.034(2) 0.048(2) 0.041(2) 0.0014(19) -0.0060(16) 0.0115(17) C4 0.0338(19) 0.039(2) 0.039(2) 0.0009(17) -0.0052(16) 0.0038(16) C5 0.0262(16) 0.0364(19) 0.0289(17) -0.0010(15) -0.0044(13) 0.0011(14) C6 0.0269(16) 0.0279(17) 0.0291(17) -0.0017(14) -0.0055(13) 0.0000(13) C7 0.0287(17) 0.0277(17) 0.0326(18) 0.0014(14) -0.0041(14) 0.0018(13) C8 0.0268(16) 0.0296(17) 0.0314(18) -0.0028(14) -0.0010(13) 0.0004(13) C9 0.0244(15) 0.0292(17) 0.0316(18) -0.0044(14) -0.0080(13) -0.0008(13) C10 0.0295(16) 0.0279(17) 0.0249(16) -0.0023(13) -0.0030(12) 0.0014(13) C11 0.0356(18) 0.0254(17) 0.0286(18) -0.0039(13) -0.0094(14) 0.0010(13) C12 0.0353(18) 0.0303(18) 0.0304(18) -0.0019(15) -0.0073(14) 0.0021(15) C13 0.042(2) 0.0334(19) 0.035(2) -0.0044(16) -0.0104(16) 0.0089(16) C14 0.055(2) 0.0277(18) 0.035(2) 0.0016(16) -0.0079(17) 0.0074(17) C15 0.049(2) 0.035(2) 0.033(2) 0.0036(16) -0.0046(17) -0.0008(17) C16 0.0376(19) 0.0334(19) 0.0319(19) -0.0017(15) -0.0046(15) 0.0006(15) C17 0.054(3) 0.056(3) 0.050(3) -0.007(2) 0.001(2) 0.018(2) C18 0.062(3) 0.060(3) 0.061(3) 0.023(3) -0.006(3) 0.012(3) C19 0.059(3) 0.070(3) 0.045(3) 0.012(2) 0.005(2) 0.001(3) C20 0.0239(15) 0.0284(17) 0.0362(19) -0.0036(14) -0.0007(13) 0.0000(13) C21 0.0278(17) 0.0345(19) 0.038(2) -0.0010(16) -0.0013(14) -0.0033(14) C22 0.0291(17) 0.0283(17) 0.045(2) -0.0017(16) 0.0046(15) -0.0032(14) C23 0.0275(17) 0.0302(18) 0.044(2) -0.0097(16) 0.0011(15) -0.0059(14) C24 0.0302(17) 0.0349(19) 0.040(2) -0.0065(16) -0.0043(15) -0.0009(15) C25 0.0317(18) 0.0301(18) 0.038(2) -0.0042(16) -0.0058(15) 0.0002(14) C26 0.064(3) 0.037(2) 0.058(3) 0.011(2) -0.011(2) -0.006(2) C27 0.062(3) 0.042(2) 0.062(3) -0.022(2) 0.012(2) -0.009(2) C28 0.072(3) 0.047(3) 0.059(3) 0.000(2) -0.033(3) 0.001(2) O1 0.059(2) 0.0512(19) 0.0461(18) 0.0022(15) -0.0001(15) 0.0274(16) O2 0.095(3) 0.0364(17) 0.053(2) 0.0119(15) -0.0001(19) 0.0199(18) O3 0.0581(19) 0.0499(19) 0.0483(19) 0.0175(15) 0.0058(15) 0.0042(15) O4 0.0425(16) 0.0331(15) 0.059(2) 0.0090(14) -0.0039(14) -0.0076(12) O5 0.0384(14) 0.0340(14) 0.0513(17) -0.0130(13) 0.0042(12) -0.0119(12) O6 0.0475(17) 0.0386(16) 0.0527(19) -0.0043(14) -0.0218(14) -0.0049(13) N3 0.0323(15) 0.0321(16) 0.0293(16) 0.0007(12) -0.0027(12) 0.0044(12) C29 0.0380(19) 0.039(2) 0.036(2) -0.0033(17) 0.0027(16) -0.0028(16) C30 0.051(2) 0.044(2) 0.044(2) 0.0014(19) 0.0097(19) -0.001(2) C31 0.064(3) 0.052(3) 0.037(2) 0.005(2) 0.005(2) 0.008(2) C32 0.058(3) 0.044(2) 0.034(2) 0.0011(18) -0.0090(19) 0.008(2) C33 0.0368(19) 0.0362(19) 0.035(2) -0.0013(16) -0.0078(16) 0.0090(16) C34 0.0334(18) 0.035(2) 0.039(2) -0.0074(17) -0.0108(15) 0.0041(15) C35 0.0307(18) 0.037(2) 0.040(2) -0.0102(17) -0.0092(15) -0.0011(15) C36 0.040(2) 0.046(2) 0.051(3) -0.005(2) -0.0092(19) -0.0134(19) C37 0.043(2) 0.055(3) 0.073(4) -0.008(3) -0.012(2) -0.017(2) C38 0.043(2) 0.067(3) 0.062(3) -0.021(3) -0.022(2) -0.010(2) C39 0.047(2) 0.052(3) 0.045(2) -0.006(2) -0.0184(19) 0.004(2) N4 0.0377(17) 0.0334(16) 0.0349(17) 0.0020(13) -0.0037(13) -0.0081(13) C40 0.041(2) 0.053(3) 0.040(2) 0.002(2) 0.0035(17) -0.0090(19) C41 0.058(3) 0.073(4) 0.050(3) 0.002(3) 0.011(2) -0.019(3) C42 0.075(3) 0.059(3) 0.048(3) 0.008(2) 0.004(2) -0.026(3) C43 0.075(3) 0.038(2) 0.045(3) 0.007(2) -0.009(2) -0.013(2) C44 0.048(2) 0.0305(19) 0.041(2) 0.0029(17) -0.0106(18) -0.0080(17) C45 0.043(2) 0.0259(18) 0.043(2) -0.0030(16) -0.0114(17) -0.0016(15) C46 0.0309(17) 0.0261(17) 0.037(2) -0.0067(15) -0.0109(14) 0.0018(14) C47 0.037(2) 0.039(2) 0.042(2) -0.0071(18) -0.0086(16) 0.0011(16) C48 0.042(2) 0.052(3) 0.050(3) -0.020(2) -0.0081(19) 0.012(2) C49 0.055(3) 0.041(2) 0.061(3) -0.016(2) -0.017(2) 0.013(2) C50 0.056(3) 0.031(2) 0.056(3) -0.0030(19) -0.014(2) 0.0051(19) P1 0.0656(8) 0.0410(6) 0.0505(7) 0.0050(5) -0.0117(6) -0.0021(6) F10 0.077(2) 0.074(2) 0.095(3) 0.022(2) -0.026(2) -0.0165(19) F11 0.175(4) 0.074(3) 0.055(2) 0.0156(19) -0.013(2) -0.014(3) F12 0.115(3) 0.098(3) 0.123(4) 0.019(3) 0.025(3) 0.048(3) F13 0.110(3) 0.114(4) 0.051(2) 0.003(2) -0.019(2) -0.026(2) F14 0.105(3) 0.068(2) 0.145(4) -0.017(3) -0.018(3) 0.028(2) F15 0.097(3) 0.106(3) 0.132(4) 0.049(3) -0.030(3) -0.046(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 C35 2.012(4) . ? Ir1 C46 2.012(4) . ? Ir1 N4 2.047(3) . ? Ir1 N3 2.053(3) . ? Ir1 N1 2.134(3) . ? Ir1 N2 2.204(3) . ? N1 C5 1.350(5) . ? N1 C1 1.353(5) . ? N2 C10 1.348(4) . ? N2 C6 1.362(5) . ? C1 C2 1.370(6) . ? C1 H1A 0.9500 . ? C2 C3 1.377(7) . ? C2 H2A 0.9500 . ? C3 C4 1.386(5) . ? C3 H3A 0.9500 . ? C4 C5 1.382(6) . ? C4 H4A 0.9500 . ? C5 C6 1.480(5) . ? C6 C7 1.386(5) . ? C7 C8 1.400(5) . ? C7 H7A 0.9500 . ? C8 C9 1.386(5) . ? C8 C20 1.476(5) . ? C9 C10 1.387(5) . ? C9 H9A 0.9500 . ? C10 C11 1.490(5) . ? C11 C16 1.389(6) . ? C11 C12 1.389(5) . ? C12 C13 1.398(5) . ? C12 H12A 0.9500 . ? C13 O1 1.361(5) . ? C13 C14 1.389(6) . ? C14 O2 1.371(5) . ? C14 C15 1.396(6) . ? C15 O3 1.363(5) . ? C15 C16 1.394(6) . ? C16 H16A 0.9500 . ? C17 O1 1.424(6) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O2 1.412(6) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O3 1.427(6) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.393(5) . ? C20 C25 1.396(5) . ? C21 C22 1.394(5) . ? C21 H21A 0.9500 . ? C22 O4 1.355(5) . ? C22 C23 1.400(6) . ? C23 O5 1.373(4) . ? C23 C24 1.384(6) . ? C24 O6 1.367(5) . ? C24 C25 1.391(5) . ? C25 H25A 0.9500 . ? C26 O4 1.422(6) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 O5 1.420(5) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 O6 1.426(6) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? N3 C29 1.337(5) . ? N3 C33 1.371(5) . ? C29 C30 1.383(6) . ? C29 H29A 0.9500 . ? C30 C31 1.389(7) . ? C30 H30A 0.9500 . ? C31 C32 1.380(7) . ? C31 H31A 0.9500 . ? C32 C33 1.384(6) . ? C32 H32A 0.9500 . ? C33 C34 1.455(6) . ? C34 C39 1.399(5) . ? C34 C35 1.405(6) . ? C35 C36 1.394(6) . ? C36 C37 1.394(6) . ? C36 H36A 0.9500 . ? C37 C38 1.381(8) . ? C37 H37A 0.9500 . ? C38 C39 1.377(8) . ? C38 H38A 0.9500 . ? C39 H39A 0.9500 . ? N4 C40 1.349(6) . ? N4 C44 1.362(5) . ? C40 C41 1.387(7) . ? C40 H40A 0.9500 . ? C41 C42 1.394(9) . ? C41 H41A 0.9500 . ? C42 C43 1.382(8) . ? C42 H42A 0.9500 . ? C43 C44 1.406(6) . ? C43 H43A 0.9500 . ? C44 C45 1.451(7) . ? C45 C46 1.398(6) . ? C45 C50 1.404(6) . ? C46 C47 1.402(6) . ? C47 C48 1.396(6) . ? C47 H47A 0.9500 . ? C48 C49 1.368(8) . ? C48 H48A 0.9500 . ? C49 C50 1.368(8) . ? C49 H49A 0.9500 . ? C50 H50A 0.9500 . ? P1 F12 1.565(4) . ? P1 F14 1.570(4) . ? P1 F15 1.572(4) . ? P1 F10 1.584(4) . ? P1 F11 1.584(4) . ? P1 F13 1.589(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C35 Ir1 C46 87.34(15) . . ? C35 Ir1 N4 91.88(16) . . ? C46 Ir1 N4 80.21(16) . . ? C35 Ir1 N3 81.01(16) . . ? C46 Ir1 N3 94.30(15) . . ? N4 Ir1 N3 171.26(13) . . ? C35 Ir1 N1 92.83(14) . . ? C46 Ir1 N1 178.76(15) . . ? N4 Ir1 N1 101.01(13) . . ? N3 Ir1 N1 84.52(12) . . ? C35 Ir1 N2 166.46(14) . . ? C46 Ir1 N2 104.66(13) . . ? N4 Ir1 N2 96.28(12) . . ? N3 Ir1 N2 91.67(12) . . ? N1 Ir1 N2 75.04(11) . . ? C5 N1 C1 118.4(3) . . ? C5 N1 Ir1 115.2(2) . . ? C1 N1 Ir1 124.7(3) . . ? C10 N2 C6 117.1(3) . . ? C10 N2 Ir1 129.5(2) . . ? C6 N2 Ir1 112.1(2) . . ? N1 C1 C2 122.3(4) . . ? N1 C1 H1A 118.9 . . ? C2 C1 H1A 118.9 . . ? C1 C2 C3 119.3(4) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C2 C3 C4 118.9(4) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C5 C4 C3 119.2(4) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? N1 C5 C4 121.6(3) . . ? N1 C5 C6 114.9(3) . . ? C4 C5 C6 123.4(3) . . ? N2 C6 C7 122.5(3) . . ? N2 C6 C5 115.8(3) . . ? C7 C6 C5 121.6(3) . . ? C6 C7 C8 120.6(3) . . ? C6 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C9 C8 C7 115.9(3) . . ? C9 C8 C20 121.9(3) . . ? C7 C8 C20 122.1(3) . . ? C8 C9 C10 121.4(3) . . ? C8 C9 H9A 119.3 . . ? C10 C9 H9A 119.3 . . ? N2 C10 C9 122.2(3) . . ? N2 C10 C11 119.4(3) . . ? C9 C10 C11 118.2(3) . . ? C16 C11 C12 121.7(3) . . ? C16 C11 C10 117.1(3) . . ? C12 C11 C10 120.9(4) . . ? C11 C12 C13 118.4(4) . . ? C11 C12 H12A 120.8 . . ? C13 C12 H12A 120.8 . . ? O1 C13 C14 115.5(4) . . ? O1 C13 C12 123.7(4) . . ? C14 C13 C12 120.8(4) . . ? O2 C14 C13 119.9(4) . . ? O2 C14 C15 120.0(4) . . ? C13 C14 C15 119.8(4) . . ? O3 C15 C16 124.2(4) . . ? O3 C15 C14 115.6(4) . . ? C16 C15 C14 120.1(4) . . ? C11 C16 C15 119.1(4) . . ? C11 C16 H16A 120.4 . . ? C15 C16 H16A 120.4 . . ? O1 C17 H17A 109.5 . . ? O1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O2 C18 H18A 109.5 . . ? O2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 119.9(3) . . ? C21 C20 C8 120.4(3) . . ? C25 C20 C8 119.7(3) . . ? C20 C21 C22 119.7(4) . . ? C20 C21 H21A 120.1 . . ? C22 C21 H21A 120.1 . . ? O4 C22 C21 124.2(4) . . ? O4 C22 C23 115.4(3) . . ? C21 C22 C23 120.3(4) . . ? O5 C23 C24 121.1(4) . . ? O5 C23 C22 119.4(4) . . ? C24 C23 C22 119.5(3) . . ? O6 C24 C23 115.6(3) . . ? O6 C24 C25 123.9(4) . . ? C23 C24 C25 120.5(4) . . ? C24 C25 C20 120.0(4) . . ? C24 C25 H25A 120.0 . . ? C20 C25 H25A 120.0 . . ? O4 C26 H26A 109.5 . . ? O4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O5 C27 H27A 109.5 . . ? O5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 C28 H28A 109.5 . . ? O6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C13 O1 C17 118.1(4) . . ? C14 O2 C18 116.6(4) . . ? C15 O3 C19 116.6(4) . . ? C22 O4 C26 116.7(3) . . ? C23 O5 C27 115.9(3) . . ? C24 O6 C28 117.3(3) . . ? C29 N3 C33 119.5(4) . . ? C29 N3 Ir1 126.3(3) . . ? C33 N3 Ir1 114.2(3) . . ? N3 C29 C30 123.1(4) . . ? N3 C29 H29A 118.4 . . ? C30 C29 H29A 118.4 . . ? C29 C30 C31 117.5(4) . . ? C29 C30 H30A 121.2 . . ? C31 C30 H30A 121.2 . . ? C32 C31 C30 119.8(4) . . ? C32 C31 H31A 120.1 . . ? C30 C31 H31A 120.1 . . ? C31 C32 C33 120.3(4) . . ? C31 C32 H32A 119.9 . . ? C33 C32 H32A 119.9 . . ? N3 C33 C32 119.7(4) . . ? N3 C33 C34 114.6(4) . . ? C32 C33 C34 125.7(4) . . ? C39 C34 C35 120.2(4) . . ? C39 C34 C33 123.8(4) . . ? C35 C34 C33 115.9(3) . . ? C36 C35 C34 118.6(4) . . ? C36 C35 Ir1 127.7(3) . . ? C34 C35 Ir1 113.4(3) . . ? C37 C36 C35 120.5(5) . . ? C37 C36 H36A 119.8 . . ? C35 C36 H36A 119.8 . . ? C38 C37 C36 120.4(5) . . ? C38 C37 H37A 119.8 . . ? C36 C37 H37A 119.8 . . ? C39 C38 C37 120.1(4) . . ? C39 C38 H38A 119.9 . . ? C37 C38 H38A 119.9 . . ? C38 C39 C34 120.2(5) . . ? C38 C39 H39A 119.9 . . ? C34 C39 H39A 119.9 . . ? C40 N4 C44 120.7(4) . . ? C40 N4 Ir1 123.7(3) . . ? C44 N4 Ir1 115.4(3) . . ? N4 C40 C41 122.1(5) . . ? N4 C40 H40A 119.0 . . ? C41 C40 H40A 119.0 . . ? C40 C41 C42 118.1(5) . . ? C40 C41 H41A 121.0 . . ? C42 C41 H41A 121.0 . . ? C43 C42 C41 120.0(5) . . ? C43 C42 H42A 120.0 . . ? C41 C42 H42A 120.0 . . ? C42 C43 C44 119.9(5) . . ? C42 C43 H43A 120.0 . . ? C44 C43 H43A 120.0 . . ? N4 C44 C43 119.2(4) . . ? N4 C44 C45 114.3(4) . . ? C43 C44 C45 126.5(4) . . ? C46 C45 C50 120.6(4) . . ? C46 C45 C44 115.5(4) . . ? C50 C45 C44 123.9(4) . . ? C45 C46 C47 117.8(4) . . ? C45 C46 Ir1 114.5(3) . . ? C47 C46 Ir1 127.7(3) . . ? C48 C47 C46 120.3(4) . . ? C48 C47 H47A 119.9 . . ? C46 C47 H47A 119.9 . . ? C49 C48 C47 121.0(5) . . ? C49 C48 H48A 119.5 . . ? C47 C48 H48A 119.5 . . ? C48 C49 C50 119.9(4) . . ? C48 C49 H49A 120.0 . . ? C50 C49 H49A 120.0 . . ? C49 C50 C45 120.3(5) . . ? C49 C50 H50A 119.9 . . ? C45 C50 H50A 119.9 . . ? F12 P1 F14 178.8(3) . . ? F12 P1 F15 92.9(3) . . ? F14 P1 F15 88.2(3) . . ? F12 P1 F10 89.0(3) . . ? F14 P1 F10 90.0(2) . . ? F15 P1 F10 177.8(3) . . ? F12 P1 F11 90.4(3) . . ? F14 P1 F11 88.9(3) . . ? F15 P1 F11 91.2(3) . . ? F10 P1 F11 90.0(2) . . ? F12 P1 F13 87.3(3) . . ? F14 P1 F13 93.3(3) . . ? F15 P1 F13 89.4(3) . . ? F10 P1 F13 89.5(2) . . ? F11 P1 F13 177.7(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.685 _refine_diff_density_min -2.180 _refine_diff_density_rms 0.102 data_pka251 _database_code_depnum_ccdc_archive 'CCDC 925643' #TrackingRef 'PKA251revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C44 H30 Ir N6 O4), 2(F6 P), C H2 Cl2, 2(H2 O)' _chemical_formula_sum 'C89 H66 Cl2 F12 Ir2 N12 O10 P2' _chemical_formula_weight 2208.83 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.776(3) _cell_length_b 14.684(5) _cell_length_c 17.409(5) _cell_angle_alpha 74.15(2) _cell_angle_beta 76.01(2) _cell_angle_gamma 72.54(2) _cell_volume 2258.2(12) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5211 _cell_measurement_theta_min 5.71 _cell_measurement_theta_max 47.57 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1086 _exptl_absorpt_coefficient_mu 3.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4074 _exptl_absorpt_correction_T_max 0.9401 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; Restraints were used to regulate problem ellipsoids in regions relating to disorder. ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30520 _diffrn_reflns_av_R_equivalents 0.1209 _diffrn_reflns_av_unetI/netI 0.0793 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.50 _reflns_number_total 9370 _reflns_number_gt 8294 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _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^)+(0.1102P)^2^+2.0536P] 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_number_reflns 9370 _refine_ls_number_parameters 640 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1711 _refine_ls_wR_factor_gt 0.1641 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.001 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 0.509340(17) 0.242399(11) 0.247954(10) 0.03168(5) Uani 1 1 d . . . N1 N 0.3668(4) 0.1904(3) 0.3549(2) 0.0335(9) Uani 1 1 d . . . N2 N 0.5794(4) 0.0823(3) 0.2638(2) 0.0340(9) Uani 1 1 d . . . C1 C 0.2549(5) 0.2500(3) 0.3947(3) 0.0381(12) Uani 1 1 d . . . H1A H 0.2344 0.3185 0.3728 0.046 Uiso 1 1 calc R . . C2 C 0.1691(6) 0.2146(4) 0.4665(3) 0.0432(13) Uani 1 1 d . . . H2A H 0.0931 0.2580 0.4944 0.052 Uiso 1 1 calc R . . C3 C 0.1975(6) 0.1149(4) 0.4959(3) 0.0456(14) Uani 1 1 d . . . H3A H 0.1404 0.0880 0.5444 0.055 Uiso 1 1 calc R . . C4 C 0.3086(6) 0.0552(4) 0.4545(3) 0.0411(13) Uani 1 1 d . . . H4A H 0.3282 -0.0136 0.4740 0.049 Uiso 1 1 calc R . . C5 C 0.3931(5) 0.0943(3) 0.3843(3) 0.0349(11) Uani 1 1 d . . . C6 C 0.5134(5) 0.0338(3) 0.3365(3) 0.0332(11) Uani 1 1 d . . . C7 C 0.5607(5) -0.0654(3) 0.3654(3) 0.0370(11) Uani 1 1 d . . . H7A H 0.5133 -0.0952 0.4163 0.044 Uiso 1 1 calc R . . C8 C 0.6752(5) -0.1223(4) 0.3221(3) 0.0403(12) Uani 1 1 d . . . C9 C 0.7400(5) -0.0751(4) 0.2485(3) 0.0390(12) Uani 1 1 d . . . H9A H 0.8193 -0.1115 0.2165 0.047 Uiso 1 1 calc R . . C10 C 0.6903(6) 0.0254(4) 0.2207(3) 0.0406(12) Uani 1 1 d . . . C11 C 0.7641(6) 0.0694(3) 0.1397(3) 0.0396(12) Uani 1 1 d . . . C12 C 0.9137(6) 0.0629(4) 0.1287(4) 0.0457(13) Uani 1 1 d . . . H12A H 0.9651 0.0331 0.1727 0.055 Uiso 1 1 calc R . . C13 C 0.9841(7) 0.0995(4) 0.0544(4) 0.0511(15) Uani 1 1 d . . . H13A H 1.0851 0.0960 0.0459 0.061 Uiso 1 1 calc R . . C14 C 0.9072(7) 0.1419(4) -0.0084(3) 0.0489(15) Uani 1 1 d . . . C15 C 0.7609(7) 0.1457(4) 0.0002(3) 0.0527(16) Uani 1 1 d . . . H15A H 0.7111 0.1729 -0.0447 0.063 Uiso 1 1 calc R . . C16 C 0.6903(6) 0.1091(4) 0.0753(3) 0.0483(15) Uani 1 1 d . . . H16A H 0.5900 0.1111 0.0831 0.058 Uiso 1 1 calc R . . N3 N 0.9802(8) 0.1849(4) -0.0881(3) 0.0689(18) Uani 1 1 d . . . O1 O 0.9162(8) 0.2178(5) -0.1441(3) 0.093(2) Uani 1 1 d . . . O2 O 1.1099(7) 0.1829(5) -0.0939(4) 0.0984(19) Uani 1 1 d . . . C17 C 0.7281(5) -0.2278(3) 0.3541(3) 0.0391(12) Uani 1 1 d . . . C18 C 0.8774(6) -0.2737(4) 0.3372(4) 0.0443(14) Uani 1 1 d . . . H18A H 0.9433 -0.2371 0.3034 0.053 Uiso 1 1 calc R . . C19 C 0.9276(6) -0.3712(4) 0.3693(4) 0.0507(15) Uani 1 1 d . . . H19A H 1.0278 -0.4031 0.3570 0.061 Uiso 1 1 calc R . . C20 C 0.8319(6) -0.4216(3) 0.4190(3) 0.0441(13) Uani 1 1 d . . . C21 C 0.6834(6) -0.3803(4) 0.4378(4) 0.0475(14) Uani 1 1 d . . . H21A H 0.6194 -0.4178 0.4724 0.057 Uiso 1 1 calc R . . C22 C 0.6326(6) -0.2820(4) 0.4039(4) 0.0434(13) Uani 1 1 d . . . H22A H 0.5316 -0.2515 0.4148 0.052 Uiso 1 1 calc R . . N4 N 0.8878(6) -0.5252(3) 0.4556(3) 0.0521(13) Uani 1 1 d . . . O3 O 1.0182(6) -0.5621(3) 0.4376(3) 0.0698(15) Uani 1 1 d . . . O4 O 0.8013(6) -0.5693(3) 0.5037(3) 0.0665(13) Uani 1 1 d . . . C23 C 0.6300(6) 0.3005(3) 0.1455(3) 0.0389(12) Uani 1 1 d . . . C24 C 0.7623(6) 0.3215(4) 0.1350(4) 0.0457(14) Uani 1 1 d . . . H24A H 0.8148 0.2982 0.1788 0.055 Uiso 1 1 calc R . . C25 C 0.8220(7) 0.3757(5) 0.0626(4) 0.0559(17) Uani 1 1 d . . . H25A H 0.9107 0.3922 0.0584 0.067 Uiso 1 1 calc R . . C26 C 0.7495(7) 0.4059(4) -0.0048(4) 0.0554(18) Uani 1 1 d . . . H26A H 0.7915 0.4401 -0.0553 0.066 Uiso 1 1 calc R . . C27 C 0.6187(7) 0.3854(4) 0.0034(4) 0.0516(16) Uani 1 1 d . . . H27A H 0.5687 0.4069 -0.0413 0.062 Uiso 1 1 calc R . . C28 C 0.5580(6) 0.3333(4) 0.0768(3) 0.0415(13) Uani 1 1 d . . . C29 C 0.4238(6) 0.3044(4) 0.0893(3) 0.0423(13) Uani 1 1 d . . . C30 C 0.3402(7) 0.3165(5) 0.0307(4) 0.0585(17) Uani 1 1 d . . . H30A H 0.3667 0.3513 -0.0229 0.070 Uiso 1 1 calc R . . C31 C 0.2199(8) 0.2789(6) 0.0497(4) 0.0678(19) Uani 1 1 d . . . H31A H 0.1639 0.2867 0.0096 0.081 Uiso 1 1 calc R . . C32 C 0.1832(7) 0.2302(5) 0.1273(4) 0.0609(17) Uani 1 1 d . . . H32A H 0.1009 0.2035 0.1422 0.073 Uiso 1 1 calc R . . C33 C 0.2658(5) 0.2203(4) 0.1835(4) 0.0460(13) Uani 1 1 d . . . H33A H 0.2390 0.1864 0.2375 0.055 Uiso 1 1 calc R . . N5 N 0.3820(5) 0.2561(3) 0.1658(3) 0.0375(10) Uani 1 1 d . . . C34 C 0.4344(6) 0.3808(3) 0.2598(3) 0.0359(12) Uani 1 1 d . . . C35 C 0.3293(6) 0.4559(4) 0.2213(3) 0.0435(13) Uani 1 1 d . . . H35A H 0.2871 0.4435 0.1826 0.052 Uiso 1 1 calc R . . C36 C 0.2859(7) 0.5490(4) 0.2390(4) 0.0565(18) Uani 1 1 d . . . H36A H 0.2164 0.5992 0.2112 0.068 Uiso 1 1 calc R . . C37 C 0.3420(7) 0.5686(4) 0.2955(4) 0.0562(17) Uani 1 1 d . . . H37A H 0.3112 0.6319 0.3073 0.067 Uiso 1 1 calc R . . C38 C 0.4448(7) 0.4951(4) 0.3357(4) 0.0539(15) Uani 1 1 d . . . H38A H 0.4836 0.5077 0.3757 0.065 Uiso 1 1 calc R . . C39 C 0.4905(5) 0.4035(4) 0.3171(3) 0.0409(12) Uani 1 1 d . . . C40 C 0.6037(5) 0.3223(4) 0.3548(3) 0.0425(12) Uani 1 1 d . . . C41 C 0.6723(6) 0.3262(4) 0.4139(4) 0.0549(15) Uani 1 1 d . . . H41A H 0.6441 0.3827 0.4363 0.066 Uiso 1 1 calc R . . C42 C 0.7826(7) 0.2473(5) 0.4406(4) 0.0606(17) Uani 1 1 d . . . H42A H 0.8305 0.2494 0.4812 0.073 Uiso 1 1 calc R . . C43 C 0.8226(6) 0.1652(4) 0.4077(4) 0.0506(15) Uani 1 1 d . . . H43A H 0.8988 0.1105 0.4244 0.061 Uiso 1 1 calc R . . C44 C 0.7477(5) 0.1658(4) 0.3499(3) 0.0411(12) Uani 1 1 d . . . H44A H 0.7736 0.1100 0.3269 0.049 Uiso 1 1 calc R . . N6 N 0.6400(5) 0.2416(3) 0.3246(3) 0.0375(10) Uani 1 1 d . . . P1 P 0.84476(18) 0.08252(14) 0.67447(11) 0.0572(4) Uani 1 1 d U . . F10 F 0.6819(6) 0.1307(6) 0.6626(5) 0.135(3) Uani 1 1 d . . . F11 F 0.8892(6) 0.1819(3) 0.6276(4) 0.0942(15) Uani 1 1 d . . . F12 F 0.8202(6) 0.1082(5) 0.7593(3) 0.121(2) Uani 1 1 d . . . F13 F 0.8062(8) -0.0168(5) 0.7150(5) 0.138(3) Uani 1 1 d U . . F14 F 0.8800(6) 0.0548(4) 0.5878(3) 0.0870(14) Uani 1 1 d . . . F15 F 1.0140(5) 0.0366(4) 0.6811(3) 0.0831(16) Uani 1 1 d . . . C10' C 0.8106(18) -0.4922(10) 0.2166(8) 0.089(8) Uani 0.25 1 d PDU A 3 H10A H 0.7488 -0.5195 0.1962 0.107 Uiso 0.25 1 calc PR A 3 H10B H 0.7478 -0.4494 0.2535 0.107 Uiso 0.25 1 calc PR A 3 C100 C 0.8024(18) -0.4879(13) 0.2276(8) 0.084(7) Uani 0.25 1 d PDU A 4 H10C H 0.7335 -0.4629 0.2735 0.101 Uiso 0.25 1 calc PR A 4 H10D H 0.7482 -0.5119 0.1993 0.101 Uiso 0.25 1 calc PR A 4 Cl1 Cl 0.9374(6) -0.5824(4) 0.2639(3) 0.1071(16) Uani 0.50 1 d PD . . Cl2 Cl 0.9052(14) -0.4353(7) 0.1454(10) 0.141(4) Uani 0.25 1 d PDU A 3 Cl2' Cl 0.8698(13) -0.3937(6) 0.1613(9) 0.122(3) Uani 0.25 1 d PDU A 4 O100 O 0.5261(18) -0.1380(18) 0.1304(15) 0.096(6) Uani 0.25 1 d PU . . O101 O 0.4951(12) -0.2563(9) 0.1644(7) 0.037(3) Uani 0.25 1 d PDU B 2 O102 O 0.5121(18) -0.0690(11) 0.0591(12) 0.062(3) Uani 0.25 1 d PU B 2 O103 O 0.7333(16) -0.3843(14) 0.1929(14) 0.080(5) Uani 0.25 1 d PDU C 2 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 0.02840(8) 0.03404(8) 0.02971(10) -0.00256(6) -0.01048(6) -0.00326(6) N1 0.0299(16) 0.0372(16) 0.0325(19) -0.0031(15) -0.0097(14) -0.0080(14) N2 0.0267(15) 0.0470(18) 0.0323(18) -0.0144(15) -0.0098(14) -0.0061(15) C1 0.032(2) 0.038(2) 0.039(2) -0.0102(18) -0.0058(18) -0.0014(18) C2 0.036(2) 0.049(2) 0.037(3) -0.011(2) -0.0024(19) -0.002(2) C3 0.042(2) 0.045(2) 0.039(3) -0.004(2) 0.001(2) -0.005(2) C4 0.038(2) 0.039(2) 0.039(3) -0.0018(19) -0.007(2) -0.0048(19) C5 0.032(2) 0.039(2) 0.029(2) -0.0041(17) -0.0096(17) -0.0015(18) C6 0.0328(19) 0.0297(18) 0.031(2) 0.0025(16) -0.0068(17) -0.0058(16) C7 0.031(2) 0.039(2) 0.037(2) -0.0043(18) -0.0075(18) -0.0054(18) C8 0.036(2) 0.042(2) 0.045(3) -0.0104(19) -0.0165(19) -0.0035(19) C9 0.037(2) 0.042(2) 0.033(2) -0.0081(19) -0.0026(19) -0.0049(19) C10 0.040(2) 0.043(2) 0.036(2) -0.0089(19) -0.0116(19) -0.002(2) C11 0.040(2) 0.038(2) 0.039(3) -0.0094(18) -0.007(2) -0.0058(19) C12 0.043(2) 0.055(3) 0.039(3) -0.008(2) -0.004(2) -0.016(2) C13 0.049(3) 0.054(3) 0.048(3) -0.011(2) -0.003(2) -0.015(2) C14 0.063(3) 0.044(2) 0.036(3) -0.015(2) 0.009(2) -0.016(2) C15 0.061(3) 0.059(3) 0.032(3) -0.010(2) -0.007(2) -0.006(3) C16 0.045(3) 0.051(3) 0.038(3) -0.008(2) -0.007(2) 0.001(2) N3 0.100(4) 0.062(3) 0.042(3) -0.018(2) 0.013(3) -0.030(3) O1 0.136(5) 0.100(4) 0.036(3) -0.004(3) 0.003(3) -0.043(4) O2 0.101(4) 0.135(4) 0.068(3) -0.037(3) 0.037(3) -0.070(3) C17 0.036(2) 0.038(2) 0.039(3) -0.0063(19) -0.0103(19) -0.0022(18) C18 0.033(2) 0.049(2) 0.045(3) -0.010(2) -0.006(2) -0.002(2) C19 0.046(3) 0.049(3) 0.049(3) -0.012(2) -0.016(2) 0.008(2) C20 0.053(3) 0.0299(19) 0.051(3) -0.0097(19) -0.023(2) 0.0008(19) C21 0.043(2) 0.040(2) 0.057(3) -0.002(2) -0.010(2) -0.013(2) C22 0.034(2) 0.037(2) 0.053(3) -0.005(2) -0.009(2) -0.0021(19) N4 0.072(3) 0.0350(18) 0.048(3) -0.0090(18) -0.023(2) -0.001(2) O3 0.076(3) 0.044(2) 0.077(3) -0.018(2) -0.031(2) 0.021(2) O4 0.095(3) 0.0430(18) 0.065(3) -0.0039(18) -0.035(2) -0.012(2) C23 0.039(2) 0.0318(19) 0.039(3) -0.0027(18) -0.005(2) -0.0039(18) C24 0.035(2) 0.054(3) 0.043(3) -0.003(2) -0.009(2) -0.009(2) C25 0.047(3) 0.057(3) 0.055(4) -0.002(3) -0.005(3) -0.013(3) C26 0.059(3) 0.053(3) 0.035(3) 0.009(2) 0.004(3) -0.013(3) C27 0.054(3) 0.050(3) 0.038(3) 0.000(2) -0.014(2) 0.001(2) C28 0.045(2) 0.038(2) 0.033(2) -0.0021(19) -0.010(2) 0.000(2) C29 0.045(2) 0.042(2) 0.036(2) -0.0037(19) -0.020(2) 0.001(2) C30 0.056(3) 0.073(3) 0.045(3) -0.013(3) -0.025(2) -0.002(3) C31 0.064(3) 0.090(4) 0.058(3) -0.020(3) -0.034(3) -0.008(3) C32 0.046(3) 0.082(4) 0.063(4) -0.017(3) -0.023(3) -0.016(3) C33 0.035(2) 0.055(2) 0.055(3) -0.015(2) -0.017(2) -0.011(2) N5 0.0391(19) 0.0369(17) 0.034(2) -0.0074(15) -0.0137(16) -0.0001(16) C34 0.043(2) 0.0198(16) 0.035(2) 0.0003(16) -0.0060(19) -0.0005(17) C35 0.047(2) 0.045(2) 0.029(2) 0.001(2) -0.014(2) 0.001(2) C36 0.055(3) 0.042(3) 0.052(3) -0.001(2) -0.011(3) 0.011(2) C37 0.056(3) 0.044(2) 0.067(4) -0.020(2) -0.006(3) -0.006(2) C38 0.049(3) 0.050(2) 0.068(4) -0.019(2) -0.020(3) -0.006(2) C39 0.035(2) 0.041(2) 0.045(3) -0.006(2) -0.005(2) -0.0106(19) C40 0.035(2) 0.046(2) 0.048(3) -0.014(2) -0.012(2) -0.0051(19) C41 0.047(3) 0.059(3) 0.067(3) -0.025(2) -0.023(2) -0.006(2) C42 0.060(3) 0.072(3) 0.057(3) -0.014(3) -0.032(3) -0.010(3) C43 0.042(2) 0.059(3) 0.052(3) -0.007(2) -0.022(2) -0.008(2) C44 0.037(2) 0.043(2) 0.043(3) -0.005(2) -0.0189(19) -0.0045(19) N6 0.0372(19) 0.0366(18) 0.034(2) -0.0013(16) -0.0150(16) -0.0016(16) P1 0.0461(7) 0.0761(9) 0.0542(9) -0.0151(7) -0.0153(6) -0.0160(7) F10 0.054(2) 0.204(6) 0.162(5) -0.052(5) -0.040(3) -0.025(3) F11 0.104(3) 0.075(2) 0.118(4) -0.007(2) -0.053(3) -0.029(2) F12 0.070(3) 0.210(5) 0.089(3) -0.086(3) -0.006(2) -0.003(3) F13 0.168(5) 0.130(4) 0.124(5) 0.027(4) -0.027(4) -0.093(3) F14 0.103(3) 0.108(3) 0.061(2) -0.018(2) -0.032(2) -0.029(3) F15 0.059(2) 0.119(3) 0.053(2) -0.009(2) -0.0167(18) 0.003(2) C10' 0.092(12) 0.126(13) 0.061(11) -0.030(11) -0.007(11) -0.041(12) C100 0.087(12) 0.125(13) 0.057(11) -0.029(11) -0.004(10) -0.048(11) Cl1 0.116(3) 0.126(3) 0.098(3) -0.020(3) -0.045(3) -0.041(3) Cl2 0.156(7) 0.070(4) 0.212(10) 0.006(6) -0.052(8) -0.067(4) Cl2' 0.157(6) 0.069(4) 0.161(8) 0.037(5) -0.074(6) -0.075(4) O100 0.031(7) 0.169(13) 0.127(13) -0.091(10) 0.001(8) -0.043(8) O101 0.033(5) 0.044(5) 0.021(4) -0.015(4) 0.007(4) 0.011(4) O102 0.069(6) 0.067(5) 0.081(6) -0.027(5) -0.035(5) -0.036(5) O103 0.074(9) 0.116(11) 0.080(12) -0.025(9) -0.023(9) -0.057(9) _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 C34 1.993(4) . ? Ir1 C23 2.014(5) . ? Ir1 N5 2.046(5) . ? Ir1 N6 2.055(5) . ? Ir1 N1 2.144(4) . ? Ir1 N2 2.201(4) . ? N1 C5 1.330(6) . ? N1 C1 1.354(6) . ? N2 C10 1.357(6) . ? N2 C6 1.383(6) . ? C1 C2 1.391(7) . ? C1 H1A 0.9500 . ? C2 C3 1.378(7) . ? C2 H2A 0.9500 . ? C3 C4 1.365(7) . ? C3 H3A 0.9500 . ? C4 C5 1.385(7) . ? C4 H4A 0.9500 . ? C5 C6 1.473(6) . ? C6 C7 1.377(6) . ? C7 C8 1.376(7) . ? C7 H7A 0.9500 . ? C8 C9 1.381(7) . ? C8 C17 1.472(7) . ? C9 C10 1.393(7) . ? C9 H9A 0.9500 . ? C10 C11 1.489(7) . ? C11 C16 1.377(8) . ? C11 C12 1.405(8) . ? C12 C13 1.359(8) . ? C12 H12A 0.9500 . ? C13 C14 1.376(9) . ? C13 H13A 0.9500 . ? C14 C15 1.387(9) . ? C14 N3 1.465(7) . ? C15 C16 1.371(8) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? N3 O1 1.196(9) . ? N3 O2 1.240(10) . ? C17 C22 1.390(7) . ? C17 C18 1.408(7) . ? C18 C19 1.370(8) . ? C18 H18A 0.9500 . ? C19 C20 1.358(8) . ? C19 H19A 0.9500 . ? C20 C21 1.390(8) . ? C20 N4 1.469(6) . ? C21 C22 1.387(7) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? N4 O3 1.226(7) . ? N4 O4 1.235(7) . ? C23 C24 1.377(8) . ? C23 C28 1.431(8) . ? C24 C25 1.393(8) . ? C24 H24A 0.9500 . ? C25 C26 1.415(10) . ? C25 H25A 0.9500 . ? C26 C27 1.366(10) . ? C26 H26A 0.9500 . ? C27 C28 1.394(8) . ? C27 H27A 0.9500 . ? C28 C29 1.447(8) . ? C29 N5 1.356(7) . ? C29 C30 1.399(9) . ? C30 C31 1.379(11) . ? C30 H30A 0.9500 . ? C31 C32 1.363(10) . ? C31 H31A 0.9500 . ? C32 C33 1.365(9) . ? C32 H32A 0.9500 . ? C33 N5 1.328(7) . ? C33 H33A 0.9500 . ? C34 C39 1.400(8) . ? C34 C35 1.405(7) . ? C35 C36 1.400(8) . ? C35 H35A 0.9500 . ? C36 C37 1.365(11) . ? C36 H36A 0.9500 . ? C37 C38 1.393(9) . ? C37 H37A 0.9500 . ? C38 C39 1.386(8) . ? C38 H38A 0.9500 . ? C39 C40 1.486(7) . ? C40 N6 1.342(7) . ? C40 C41 1.379(9) . ? C41 C42 1.385(8) . ? C41 H41A 0.9500 . ? C42 C43 1.385(10) . ? C42 H42A 0.9500 . ? C43 C44 1.377(9) . ? C43 H43A 0.9500 . ? C44 N6 1.339(6) . ? C44 H44A 0.9500 . ? P1 F13 1.551(7) . ? P1 F12 1.568(6) . ? P1 F10 1.575(5) . ? P1 F11 1.594(5) . ? P1 F14 1.600(5) . ? P1 F15 1.608(5) . ? C10' Cl2 1.560(19) . ? C10' Cl1 1.698(14) . ? C10' H10A 0.9900 . ? C10' H10B 0.9900 . ? C100 Cl1 1.701(14) . ? C100 Cl2' 1.73(2) . ? C100 H10C 0.9900 . ? C100 H10D 0.9900 . ? O100 O102 1.38(3) . ? O100 O101 1.77(3) . ? 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 C34 Ir1 C23 83.3(2) . . ? C34 Ir1 N5 95.2(2) . . ? C23 Ir1 N5 80.2(2) . . ? C34 Ir1 N6 80.6(2) . . ? C23 Ir1 N6 95.7(2) . . ? N5 Ir1 N6 174.53(15) . . ? C34 Ir1 N1 93.19(17) . . ? C23 Ir1 N1 175.47(15) . . ? N5 Ir1 N1 97.28(17) . . ? N6 Ir1 N1 86.54(17) . . ? C34 Ir1 N2 167.52(17) . . ? C23 Ir1 N2 107.78(17) . . ? N5 Ir1 N2 92.36(16) . . ? N6 Ir1 N2 92.37(16) . . ? N1 Ir1 N2 75.98(14) . . ? C5 N1 C1 118.8(4) . . ? C5 N1 Ir1 117.7(3) . . ? C1 N1 Ir1 123.5(3) . . ? C10 N2 C6 115.8(4) . . ? C10 N2 Ir1 130.3(3) . . ? C6 N2 Ir1 113.0(3) . . ? N1 C1 C2 122.4(4) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C3 C2 C1 118.0(5) . . ? C3 C2 H2A 121.0 . . ? C1 C2 H2A 121.0 . . ? C4 C3 C2 119.2(5) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 120.5(5) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? N1 C5 C4 121.1(4) . . ? N1 C5 C6 115.8(4) . . ? C4 C5 C6 123.1(4) . . ? C7 C6 N2 122.4(4) . . ? C7 C6 C5 120.9(4) . . ? N2 C6 C5 116.7(4) . . ? C8 C7 C6 121.3(5) . . ? C8 C7 H7A 119.3 . . ? C6 C7 H7A 119.3 . . ? C7 C8 C9 116.8(4) . . ? C7 C8 C17 121.3(5) . . ? C9 C8 C17 121.9(4) . . ? C8 C9 C10 120.7(4) . . ? C8 C9 H9A 119.7 . . ? C10 C9 H9A 119.7 . . ? N2 C10 C9 122.9(5) . . ? N2 C10 C11 120.2(4) . . ? C9 C10 C11 116.9(4) . . ? C16 C11 C12 120.5(5) . . ? C16 C11 C10 120.8(5) . . ? C12 C11 C10 118.5(5) . . ? C13 C12 C11 119.4(6) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C12 C13 C14 119.1(6) . . ? C12 C13 H13A 120.4 . . ? C14 C13 H13A 120.4 . . ? C13 C14 C15 122.6(5) . . ? C13 C14 N3 119.8(6) . . ? C15 C14 N3 117.6(6) . . ? C16 C15 C14 117.9(6) . . ? C16 C15 H15A 121.0 . . ? C14 C15 H15A 121.0 . . ? C15 C16 C11 120.4(6) . . ? C15 C16 H16A 119.8 . . ? C11 C16 H16A 119.8 . . ? O1 N3 O2 123.1(6) . . ? O1 N3 C14 120.4(7) . . ? O2 N3 C14 116.6(6) . . ? C22 C17 C18 119.5(4) . . ? C22 C17 C8 120.5(4) . . ? C18 C17 C8 119.9(5) . . ? C19 C18 C17 120.0(5) . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C20 C19 C18 119.0(5) . . ? C20 C19 H19A 120.5 . . ? C18 C19 H19A 120.5 . . ? C19 C20 C21 123.6(5) . . ? C19 C20 N4 118.5(5) . . ? C21 C20 N4 117.9(5) . . ? C22 C21 C20 117.2(5) . . ? C22 C21 H21A 121.4 . . ? C20 C21 H21A 121.4 . . ? C21 C22 C17 120.7(5) . . ? C21 C22 H22A 119.7 . . ? C17 C22 H22A 119.7 . . ? O3 N4 O4 124.0(5) . . ? O3 N4 C20 117.8(5) . . ? O4 N4 C20 118.2(5) . . ? C24 C23 C28 116.8(5) . . ? C24 C23 Ir1 129.2(4) . . ? C28 C23 Ir1 113.6(4) . . ? C23 C24 C25 122.4(6) . . ? C23 C24 H24A 118.8 . . ? C25 C24 H24A 118.8 . . ? C24 C25 C26 119.5(6) . . ? C24 C25 H25A 120.3 . . ? C26 C25 H25A 120.3 . . ? C27 C26 C25 119.5(5) . . ? C27 C26 H26A 120.3 . . ? C25 C26 H26A 120.3 . . ? C26 C27 C28 120.6(6) . . ? C26 C27 H27A 119.7 . . ? C28 C27 H27A 119.7 . . ? C27 C28 C23 121.1(6) . . ? C27 C28 C29 124.0(5) . . ? C23 C28 C29 114.8(4) . . ? N5 C29 C30 118.3(5) . . ? N5 C29 C28 114.6(5) . . ? C30 C29 C28 127.0(5) . . ? C31 C30 C29 121.0(6) . . ? C31 C30 H30A 119.5 . . ? C29 C30 H30A 119.5 . . ? C32 C31 C30 118.3(7) . . ? C32 C31 H31A 120.8 . . ? C30 C31 H31A 120.8 . . ? C31 C32 C33 119.5(7) . . ? C31 C32 H32A 120.3 . . ? C33 C32 H32A 120.3 . . ? N5 C33 C32 122.7(6) . . ? N5 C33 H33A 118.7 . . ? C32 C33 H33A 118.7 . . ? C33 N5 C29 120.2(5) . . ? C33 N5 Ir1 124.0(4) . . ? C29 N5 Ir1 115.8(4) . . ? C39 C34 C35 116.7(4) . . ? C39 C34 Ir1 114.7(3) . . ? C35 C34 Ir1 128.5(4) . . ? C36 C35 C34 120.9(6) . . ? C36 C35 H35A 119.6 . . ? C34 C35 H35A 119.6 . . ? C37 C36 C35 121.0(5) . . ? C37 C36 H36A 119.5 . . ? C35 C36 H36A 119.5 . . ? C36 C37 C38 119.4(6) . . ? C36 C37 H37A 120.3 . . ? C38 C37 H37A 120.3 . . ? C39 C38 C37 119.8(6) . . ? C39 C38 H38A 120.1 . . ? C37 C38 H38A 120.1 . . ? C38 C39 C34 122.2(5) . . ? C38 C39 C40 123.2(6) . . ? C34 C39 C40 114.6(4) . . ? N6 C40 C41 120.6(5) . . ? N6 C40 C39 114.1(5) . . ? C41 C40 C39 125.3(5) . . ? C40 C41 C42 119.6(6) . . ? C40 C41 H41A 120.2 . . ? C42 C41 H41A 120.2 . . ? C43 C42 C41 119.7(7) . . ? C43 C42 H42A 120.1 . . ? C41 C42 H42A 120.1 . . ? C44 C43 C42 117.5(5) . . ? C44 C43 H43A 121.3 . . ? C42 C43 H43A 121.3 . . ? N6 C44 C43 123.0(5) . . ? N6 C44 H44A 118.5 . . ? C43 C44 H44A 118.5 . . ? C44 N6 C40 119.7(5) . . ? C44 N6 Ir1 125.1(4) . . ? C40 N6 Ir1 115.0(3) . . ? F13 P1 F12 91.1(4) . . ? F13 P1 F10 89.9(4) . . ? F12 P1 F10 94.2(4) . . ? F13 P1 F11 176.3(4) . . ? F12 P1 F11 92.5(4) . . ? F10 P1 F11 91.0(4) . . ? F13 P1 F14 89.7(4) . . ? F12 P1 F14 176.6(3) . . ? F10 P1 F14 89.1(4) . . ? F11 P1 F14 86.7(3) . . ? F13 P1 F15 92.6(4) . . ? F12 P1 F15 88.2(3) . . ? F10 P1 F15 176.6(3) . . ? F11 P1 F15 86.4(3) . . ? F14 P1 F15 88.4(3) . . ? Cl2 C10' Cl1 102.8(11) . . ? Cl2 C10' H10A 111.2 . . ? Cl1 C10' H10A 111.2 . . ? Cl2 C10' H10B 111.2 . . ? Cl1 C10' H10B 111.2 . . ? H10A C10' H10B 109.1 . . ? Cl1 C100 Cl2' 111.9(11) . . ? Cl1 C100 H10C 109.2 . . ? Cl2' C100 H10C 109.2 . . ? Cl1 C100 H10D 109.2 . . ? Cl2' C100 H10D 109.2 . . ? H10C C100 H10D 107.9 . . ? C10' Cl1 C100 7.0(6) . . ? O102 O100 O101 132.6(18) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.737 _refine_diff_density_min -5.261 _refine_diff_density_rms 0.217