# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- acrispinirevised.CIF' _publ_contact_author_name 'Crispini, Alessandra' _publ_contact_author_address ; Dipartimento di Scienze Farmaceutiche Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; _publ_contact_author_email a.crispini@unical.it _publ_contact_author_fax 0984492066 _publ_contact_author_phone 0984492888 _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication as a Comunication in Dalton Transactions ; _publ_requested_category FP _publ_section_title ; Tuning Solid State Luminescent Properties in Hydrogen Bonding-Directed Supramolecular Assembly of Bis-Cyclometalated Iridium(III) Ethylenediamine Complexes. ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_address A.M.Talarico ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; E.I.Szerb ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; T.Mastropietro ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; I.Aiello ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; A.Crispini ; Dipartimento di Scienze Farmaceutiche Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; ; M.Ghedini ; ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; data_(1c) _database_code_depnum_ccdc_archive 'CCDC 850263' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C24 H24 Ir N4, Cl O4' _chemical_formula_sum 'C24 H24 Cl Ir N4 O4' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _diffrn_ambient_temperature 298(2) _chemical_formula_weight 660.12 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_int_tables_number 33 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 12.8971(17) _cell_length_b 16.631(2) _cell_length_c 10.9986(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2359.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7018 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 27.49 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.859 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 5.812 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6535 _exptl_absorpt_correction_T_max 0.8449 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45604 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 32.00 _reflns_number_total 7728 _reflns_number_gt 5447 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0278P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(6) _refine_ls_number_reflns 7728 _refine_ls_number_parameters 326 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0589 _refine_ls_wR_factor_gt 0.0509 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _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 0.581057(8) 0.283613(6) 0.26345(4) 0.04246(4) Uani 1 1 d . . . N1 N 0.6988(3) 0.20693(17) 0.1785(3) 0.0531(8) Uani 1 1 d . . . H1A H 0.7368 0.2361 0.1258 0.064 Uiso 1 1 calc R . . H1B H 0.7416 0.1872 0.2358 0.064 Uiso 1 1 calc R . . N2 N 0.4871(2) 0.17891(18) 0.2113(3) 0.0544(8) Uani 1 1 d . . . H2A H 0.4426 0.1665 0.2716 0.065 Uiso 1 1 calc R . . H2B H 0.4500 0.1902 0.1441 0.065 Uiso 1 1 calc R . . N3 N 0.6202(3) 0.2414(2) 0.4313(3) 0.0476(7) Uani 1 1 d . . . N4 N 0.5339(2) 0.34306(18) 0.1090(3) 0.0502(7) Uani 1 1 d . . . C1 C 0.6860(3) 0.3664(2) 0.3089(3) 0.0484(9) Uani 1 1 d . . . C2 C 0.7241(3) 0.4305(2) 0.2420(5) 0.0596(15) Uani 1 1 d . . . H2 H 0.6966 0.4411 0.1655 0.071 Uiso 1 1 calc R . . C3 C 0.8028(3) 0.4794(2) 0.2870(6) 0.0672(17) Uani 1 1 d . . . H3 H 0.8261 0.5222 0.2400 0.081 Uiso 1 1 calc R . . C4 C 0.8464(3) 0.4666(3) 0.3969(5) 0.0738(14) Uani 1 1 d . . . H4 H 0.8997 0.4998 0.4240 0.089 Uiso 1 1 calc R . . C5 C 0.8113(3) 0.4037(3) 0.4698(5) 0.0655(13) Uani 1 1 d . . . H5 H 0.8397 0.3947 0.5462 0.079 Uiso 1 1 calc R . . C6 C 0.7320(3) 0.3545(2) 0.4247(4) 0.0507(9) Uani 1 1 d . . . C7 C 0.6892(3) 0.2865(2) 0.4944(4) 0.0527(10) Uani 1 1 d . . . C8 C 0.7110(5) 0.2687(3) 0.6159(5) 0.0753(14) Uani 1 1 d . . . H8 H 0.7603 0.2987 0.6578 0.090 Uiso 1 1 calc R . . C9 C 0.6605(5) 0.2075(3) 0.6731(5) 0.0814(16) Uani 1 1 d . . . H9 H 0.6738 0.1962 0.7545 0.098 Uiso 1 1 calc R . . C10 C 0.5899(4) 0.1628(3) 0.6089(5) 0.0705(13) Uani 1 1 d . . . H10 H 0.5540 0.1212 0.6464 0.085 Uiso 1 1 calc R . . C11 C 0.5732(3) 0.1801(3) 0.4902(5) 0.0629(12) Uani 1 1 d . . . H11A H 0.5270 0.1481 0.4470 0.076 Uiso 1 1 calc R . . C12 C 0.4659(3) 0.3500(2) 0.3343(4) 0.0533(10) Uani 1 1 d . . . C13 C 0.4288(4) 0.3517(3) 0.4531(5) 0.0708(13) Uani 1 1 d . . . H13 H 0.4584 0.3179 0.5109 0.085 Uiso 1 1 calc R . . C14 C 0.3482(4) 0.4026(3) 0.4874(6) 0.0862(17) Uani 1 1 d . . . H14 H 0.3247 0.4027 0.5673 0.103 Uiso 1 1 calc R . . C15 C 0.3034(4) 0.4530(3) 0.4029(6) 0.0841(17) Uani 1 1 d . . . H15 H 0.2493 0.4867 0.4258 0.101 Uiso 1 1 calc R . . C16 C 0.3372(3) 0.4537(2) 0.2881(6) 0.0696(17) Uani 1 1 d . . . H16 H 0.3071 0.4884 0.2321 0.084 Uiso 1 1 calc R . . C17 C 0.4174(2) 0.4026(2) 0.2513(9) 0.0600(14) Uani 1 1 d . . . C18 C 0.4563(3) 0.3980(2) 0.1246(5) 0.0569(11) Uani 1 1 d . . . C19 C 0.4214(3) 0.4424(3) 0.0261(6) 0.0773(16) Uani 1 1 d . . . H19 H 0.3691 0.4802 0.0370 0.093 Uiso 1 1 calc R . . C20 C 0.4632(4) 0.4310(3) -0.0874(6) 0.0808(15) Uani 1 1 d . . . H20 H 0.4393 0.4603 -0.1537 0.097 Uiso 1 1 calc R . . C21 C 0.5398(4) 0.3764(3) -0.1007(5) 0.0746(13) Uani 1 1 d . . . H21 H 0.5685 0.3671 -0.1770 0.090 Uiso 1 1 calc R . . C22 C 0.5749(3) 0.3348(3) -0.0014(5) 0.0629(12) Uani 1 1 d . . . H22 H 0.6298 0.2992 -0.0115 0.075 Uiso 1 1 calc R . . C23 C 0.5569(3) 0.1106(3) 0.1878(5) 0.0660(12) Uani 1 1 d . . . H23A H 0.5201 0.0688 0.1439 0.079 Uiso 1 1 calc R . . H23B H 0.5813 0.0883 0.2640 0.079 Uiso 1 1 calc R . . C24 C 0.6474(3) 0.1399(2) 0.1135(4) 0.0611(11) Uani 1 1 d . . . H24A H 0.6963 0.0963 0.1011 0.073 Uiso 1 1 calc R . . H24B H 0.6234 0.1580 0.0346 0.073 Uiso 1 1 calc R . . Cl1 Cl 0.3869(5) 0.1381(5) -0.0978(6) 0.0908(17) Uani 0.610(11) 1 d P A 1 O4 O 0.3986(6) 0.0726(6) -0.0197(7) 0.149(5) Uani 0.610(11) 1 d P A 1 Cl1A Cl 0.3784(7) 0.1722(6) -0.1175(9) 0.079(2) Uani 0.390(11) 1 d P A 2 O4A O 0.3856(18) 0.2343(10) -0.198(2) 0.213(16) Uani 0.390(11) 1 d P A 2 O1 O 0.3241(5) 0.1158(3) -0.1873(5) 0.204(4) Uani 1 1 d . . . O2 O 0.4835(4) 0.1595(5) -0.1163(6) 0.167(3) Uani 1 1 d . . . O3 O 0.3391(5) 0.2026(6) -0.0198(9) 0.210(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.03884(7) 0.03701(6) 0.05153(7) 0.00021(13) -0.00275(13) 0.00257(4) N1 0.0503(19) 0.050(2) 0.059(2) -0.0025(15) -0.0105(16) 0.0100(14) N2 0.0511(19) 0.0468(17) 0.065(2) -0.0029(15) -0.0071(15) -0.0003(15) N3 0.0471(17) 0.0459(17) 0.0498(19) 0.0010(15) 0.0015(15) 0.0040(15) N4 0.0437(17) 0.0400(17) 0.067(2) 0.0052(16) -0.0086(17) 0.0006(14) C1 0.0438(19) 0.042(2) 0.059(2) -0.0049(15) 0.0059(16) 0.0020(15) C2 0.056(2) 0.0480(19) 0.075(5) -0.004(2) 0.007(2) 0.0021(16) C3 0.060(2) 0.046(2) 0.095(5) -0.007(3) 0.022(3) -0.0075(17) C4 0.050(3) 0.063(3) 0.109(4) -0.038(3) 0.007(3) -0.009(2) C5 0.050(2) 0.069(3) 0.077(3) -0.037(3) 0.003(2) -0.004(2) C6 0.043(2) 0.050(2) 0.059(2) -0.0139(19) 0.0029(18) 0.0052(17) C7 0.053(2) 0.055(2) 0.050(2) -0.0076(19) -0.0028(19) 0.0063(18) C8 0.082(4) 0.085(4) 0.059(3) -0.010(3) -0.009(3) 0.003(3) C9 0.103(5) 0.091(4) 0.050(3) 0.011(3) -0.004(3) 0.012(3) C10 0.080(3) 0.070(3) 0.062(3) 0.013(2) 0.009(2) 0.005(2) C11 0.069(3) 0.058(3) 0.062(3) 0.007(2) 0.000(2) 0.000(2) C12 0.042(2) 0.044(2) 0.074(3) -0.005(2) 0.006(2) -0.0040(17) C13 0.070(3) 0.057(3) 0.086(4) -0.005(3) 0.015(2) 0.002(2) C14 0.074(3) 0.064(3) 0.120(5) -0.026(3) 0.037(3) -0.006(3) C15 0.051(3) 0.057(3) 0.145(6) -0.031(3) 0.008(3) 0.006(2) C16 0.045(2) 0.047(2) 0.117(5) -0.017(3) -0.003(3) 0.0004(16) C17 0.0384(16) 0.0368(16) 0.105(4) -0.011(3) -0.011(3) -0.0028(13) C18 0.0375(19) 0.041(2) 0.092(3) 0.009(2) -0.014(2) -0.0032(17) C19 0.057(3) 0.055(3) 0.119(5) 0.027(3) -0.023(3) -0.002(2) C20 0.064(3) 0.080(4) 0.098(4) 0.040(3) -0.018(3) -0.005(3) C21 0.079(3) 0.074(3) 0.071(3) 0.026(3) -0.013(3) -0.009(3) C22 0.059(3) 0.063(3) 0.067(3) 0.010(2) -0.004(2) 0.001(2) C23 0.070(3) 0.044(2) 0.084(3) -0.013(2) -0.023(3) 0.004(2) C24 0.064(3) 0.054(2) 0.066(3) -0.012(2) -0.012(2) 0.014(2) Cl1 0.072(3) 0.135(5) 0.065(2) 0.019(3) -0.0102(17) -0.043(3) O4 0.175(8) 0.175(9) 0.096(6) 0.059(6) -0.077(5) -0.075(7) Cl1A 0.067(3) 0.114(6) 0.056(3) 0.001(4) -0.018(2) -0.013(4) O4A 0.25(2) 0.141(12) 0.25(3) 0.066(16) -0.18(2) -0.096(12) O1 0.284(7) 0.154(4) 0.175(6) 0.089(4) -0.167(6) -0.125(5) O2 0.092(4) 0.247(8) 0.163(5) -0.026(5) -0.001(4) -0.019(4) O3 0.120(6) 0.330(10) 0.180(8) -0.040(7) 0.049(5) 0.016(5) _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 C1 1.994(4) . ? Ir1 C12 2.008(4) . ? Ir1 N3 2.039(3) . ? Ir1 N4 2.057(3) . ? Ir1 N1 2.192(3) . ? Ir1 N2 2.198(3) . ? N1 C24 1.481(5) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N2 C23 1.473(5) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N3 C11 1.351(6) . ? N3 C7 1.355(5) . ? N4 C22 1.331(6) . ? N4 C18 1.365(5) . ? C1 C2 1.386(6) . ? C1 C6 1.419(5) . ? C2 C3 1.392(6) . ? C2 H2 0.9300 . ? C3 C4 1.350(8) . ? C3 H3 0.9300 . ? C4 C5 1.393(7) . ? C4 H4 0.9300 . ? C5 C6 1.400(6) . ? C5 H5 0.9300 . ? C6 C7 1.474(6) . ? C7 C8 1.398(7) . ? C8 C9 1.362(7) . ? C8 H8 0.9300 . ? C9 C10 1.371(7) . ? C9 H9 0.9300 . ? C10 C11 1.354(7) . ? C10 H10 0.9300 . ? C11 H11A 0.9300 . ? C12 C13 1.392(7) . ? C12 C17 1.411(8) . ? C13 C14 1.393(6) . ? C13 H13 0.9300 . ? C14 C15 1.378(8) . ? C14 H14 0.9300 . ? C15 C16 1.336(9) . ? C15 H15 0.9300 . ? C16 C17 1.397(6) . ? C16 H16 0.9300 . ? C17 C18 1.484(10) . ? C18 C19 1.386(7) . ? C19 C20 1.373(8) . ? C19 H19 0.9300 . ? C20 C21 1.349(8) . ? C20 H20 0.9300 . ? C21 C22 1.371(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.505(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? Cl1 O2 1.311(8) . ? Cl1 O1 1.327(7) . ? Cl1 O4 1.396(10) . ? Cl1 O3 1.505(11) . ? Cl1A O3 1.291(13) . ? Cl1A O4A 1.36(2) . ? Cl1A O2 1.372(11) . ? Cl1A O1 1.399(10) . ? 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 Ir1 C12 91.43(16) . . ? C1 Ir1 N3 80.97(15) . . ? C12 Ir1 N3 91.21(16) . . ? C1 Ir1 N4 94.34(14) . . ? C12 Ir1 N4 80.64(16) . . ? N3 Ir1 N4 170.53(13) . . ? C1 Ir1 N1 92.20(14) . . ? C12 Ir1 N1 176.08(15) . . ? N3 Ir1 N1 90.82(13) . . ? N4 Ir1 N1 97.62(14) . . ? C1 Ir1 N2 170.64(13) . . ? C12 Ir1 N2 97.41(14) . . ? N3 Ir1 N2 95.72(13) . . ? N4 Ir1 N2 90.13(12) . . ? N1 Ir1 N2 79.05(13) . . ? C24 N1 Ir1 109.5(2) . . ? C24 N1 H1A 109.8 . . ? Ir1 N1 H1A 109.8 . . ? C24 N1 H1B 109.8 . . ? Ir1 N1 H1B 109.8 . . ? H1A N1 H1B 108.2 . . ? C23 N2 Ir1 108.7(2) . . ? C23 N2 H2A 110.0 . . ? Ir1 N2 H2A 110.0 . . ? C23 N2 H2B 110.0 . . ? Ir1 N2 H2B 110.0 . . ? H2A N2 H2B 108.3 . . ? C11 N3 C7 117.8(4) . . ? C11 N3 Ir1 125.7(3) . . ? C7 N3 Ir1 115.8(3) . . ? C22 N4 C18 118.3(4) . . ? C22 N4 Ir1 125.9(3) . . ? C18 N4 Ir1 115.8(3) . . ? C2 C1 C6 115.8(4) . . ? C2 C1 Ir1 129.8(3) . . ? C6 C1 Ir1 114.4(3) . . ? C1 C2 C3 121.3(5) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 122.0(5) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 119.9(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 118.2(5) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C5 C6 C1 122.8(4) . . ? C5 C6 C7 122.5(4) . . ? C1 C6 C7 114.6(4) . . ? N3 C7 C8 120.3(4) . . ? N3 C7 C6 113.9(4) . . ? C8 C7 C6 125.8(4) . . ? C9 C8 C7 120.2(5) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 119.0(5) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 119.1(5) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? N3 C11 C10 123.5(5) . . ? N3 C11 H11A 118.3 . . ? C10 C11 H11A 118.3 . . ? C13 C12 C17 116.3(5) . . ? C13 C12 Ir1 129.0(4) . . ? C17 C12 Ir1 114.7(4) . . ? C12 C13 C14 121.5(5) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 120.0(6) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 120.4(5) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 120.7(6) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 121.2(8) . . ? C16 C17 C18 123.7(6) . . ? C12 C17 C18 115.1(4) . . ? N4 C18 C19 119.8(5) . . ? N4 C18 C17 113.6(4) . . ? C19 C18 C17 126.6(4) . . ? C20 C19 C18 120.6(5) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C21 C20 C19 118.6(5) . . ? C21 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? C20 C21 C22 119.6(6) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? N4 C22 C21 123.0(5) . . ? N4 C22 H22 118.5 . . ? C21 C22 H22 118.5 . . ? N2 C23 C24 108.7(3) . . ? N2 C23 H23A 110.0 . . ? C24 C23 H23A 110.0 . . ? N2 C23 H23B 110.0 . . ? C24 C23 H23B 110.0 . . ? H23A C23 H23B 108.3 . . ? N1 C24 C23 109.2(4) . . ? N1 C24 H24A 109.8 . . ? C23 C24 H24A 109.8 . . ? N1 C24 H24B 109.8 . . ? C23 C24 H24B 109.8 . . ? H24A C24 H24B 108.3 . . ? O2 Cl1 O1 122.7(6) . . ? O2 Cl1 O4 101.7(7) . . ? O1 Cl1 O4 107.7(6) . . ? O2 Cl1 O3 106.5(6) . . ? O1 Cl1 O3 111.9(7) . . ? O4 Cl1 O3 104.4(7) . . ? O3 Cl1A O4A 105.6(14) . . ? O3 Cl1A O2 116.1(8) . . ? O4A Cl1A O2 93.2(12) . . ? O3 Cl1A O1 121.5(9) . . ? O4A Cl1A O1 100.8(9) . . ? O2 Cl1A O1 113.3(8) . . ? Cl1 O1 Cl1A 25.9(3) . . ? Cl1 O2 Cl1A 26.4(3) . . ? Cl1A O3 Cl1 23.9(4) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 32.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.422 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.076 #===END data_(2a) _database_code_depnum_ccdc_archive 'CCDC 850264' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Ir N4, F6 P' _chemical_formula_sum 'C24 H24 F6 Ir N4 P' _chemical_formula_weight 705.64 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 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' _cell_length_a 7.9909(6) _cell_length_b 10.6437(8) _cell_length_c 14.8207(15) _cell_angle_alpha 78.458(3) _cell_angle_beta 81.685(4) _cell_angle_gamma 80.293(3) _cell_volume 1209.32(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Parallelepiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.938 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 5.654 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6017 _exptl_absorpt_correction_T_max 0.8953 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8477 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4250 _reflns_number_gt 3938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius X8 APEX' _computing_cell_refinement 'Bruker-Nonius X8 APEX' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material ? _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^)+(0.0479P)^2^+8.9784P] 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 0.0032(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4250 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 0.20292(4) 0.19316(3) 0.22205(2) 0.03133(15) Uani 1 1 d . . . P1 P 0.2316(3) -0.2740(2) 0.09160(18) 0.0424(5) Uani 1 1 d . . . N1 N 0.1498(10) 0.1145(7) 0.1039(5) 0.0422(17) Uani 1 1 d . . . H1A H 0.1808 0.0280 0.1133 0.051 Uiso 1 1 calc R . . H1B H 0.0374 0.1317 0.0978 0.051 Uiso 1 1 calc R . . N2 N 0.3050(9) 0.3325(7) 0.1054(5) 0.0408(16) Uani 1 1 d . . . H2A H 0.2711 0.4138 0.1160 0.049 Uiso 1 1 calc R . . H2B H 0.4200 0.3178 0.0989 0.049 Uiso 1 1 calc R . . N3 N 0.4113(9) 0.0527(6) 0.2301(5) 0.0370(15) Uani 1 1 d . . . N4 N -0.0103(9) 0.3302(7) 0.2313(5) 0.0370(15) Uani 1 1 d . . . F1 F 0.3535(13) -0.3354(11) 0.0134(8) 0.140(4) Uani 1 1 d . . . F2 F 0.3599(10) -0.1748(7) 0.0891(6) 0.090(2) Uani 1 1 d . . . F3 F 0.1038(9) -0.3707(7) 0.0901(6) 0.088(2) Uani 1 1 d . . . F4 F 0.3202(14) -0.3737(10) 0.1662(8) 0.139(4) Uani 1 1 d . . . F5 F 0.1444(14) -0.1756(9) 0.0123(8) 0.135(4) Uani 1 1 d . . . F6 F 0.1086(12) -0.2064(11) 0.1613(8) 0.133(4) Uani 1 1 d . . . C1 C 0.1014(11) 0.0559(8) 0.3175(6) 0.0392(19) Uani 1 1 d . . . C2 C -0.0629(13) 0.0586(10) 0.3630(7) 0.052(2) Uani 1 1 d . . . H2 H -0.1399 0.1345 0.3522 0.062 Uiso 1 1 calc R . . C3 C -0.1163(16) -0.0457(12) 0.4231(7) 0.063(3) Uani 1 1 d . . . H3 H -0.2273 -0.0402 0.4529 0.076 Uiso 1 1 calc R . . C4 C -0.0022(18) -0.1613(11) 0.4395(8) 0.071(3) Uani 1 1 d . . . H4 H -0.0387 -0.2332 0.4794 0.085 Uiso 1 1 calc R . . C5 C 0.1607(16) -0.1693(10) 0.3977(7) 0.058(3) Uani 1 1 d . . . H5 H 0.2362 -0.2458 0.4093 0.070 Uiso 1 1 calc R . . C6 C 0.2145(12) -0.0605(8) 0.3366(6) 0.042(2) Uani 1 1 d . . . C7 C 0.3904(12) -0.0592(8) 0.2904(6) 0.042(2) Uani 1 1 d . . . C8 C 0.5269(16) -0.1553(9) 0.3066(8) 0.060(3) Uani 1 1 d . . . H8 H 0.5111 -0.2298 0.3501 0.071 Uiso 1 1 calc R . . C9 C 0.6873(16) -0.1428(11) 0.2593(9) 0.069(3) Uani 1 1 d . . . H9 H 0.7791 -0.2084 0.2694 0.083 Uiso 1 1 calc R . . C10 C 0.7067(13) -0.0292(9) 0.1963(8) 0.054(2) Uani 1 1 d . . . H10 H 0.8122 -0.0171 0.1626 0.065 Uiso 1 1 calc R . . C11 C 0.5687(12) 0.0642(8) 0.1848(7) 0.047(2) Uani 1 1 d . . . H11 H 0.5836 0.1405 0.1432 0.056 Uiso 1 1 calc R . . C12 C 0.2617(12) 0.2785(8) 0.3201(6) 0.0393(19) Uani 1 1 d . . . C13 C 0.4077(13) 0.2484(10) 0.3667(7) 0.050(2) Uani 1 1 d . . . H13 H 0.4877 0.1766 0.3573 0.060 Uiso 1 1 calc R . . C14 C 0.4328(17) 0.3266(13) 0.4275(8) 0.067(3) Uani 1 1 d . . . H14 H 0.5304 0.3058 0.4580 0.081 Uiso 1 1 calc R . . C15 C 0.3185(17) 0.4322(13) 0.4434(8) 0.069(3) Uani 1 1 d . . . H15 H 0.3391 0.4834 0.4835 0.083 Uiso 1 1 calc R . . C16 C 0.1736(16) 0.4628(10) 0.4001(8) 0.060(3) Uani 1 1 d . . . H16 H 0.0942 0.5340 0.4116 0.073 Uiso 1 1 calc R . . C17 C 0.1443(13) 0.3875(8) 0.3387(6) 0.042(2) Uani 1 1 d . . . C18 C -0.0091(12) 0.4106(8) 0.2923(6) 0.0403(19) Uani 1 1 d . . . C19 C -0.1528(15) 0.5043(10) 0.3065(8) 0.060(3) Uani 1 1 d . . . H19 H -0.1524 0.5615 0.3463 0.072 Uiso 1 1 calc R . . C20 C -0.2947(15) 0.5111(10) 0.2612(9) 0.064(3) Uani 1 1 d . . . H20 H -0.3918 0.5701 0.2724 0.077 Uiso 1 1 calc R . . C21 C -0.2907(13) 0.4301(10) 0.1995(9) 0.059(3) Uani 1 1 d . . . H21 H -0.3832 0.4355 0.1667 0.070 Uiso 1 1 calc R . . C22 C -0.1491(12) 0.3416(9) 0.1870(7) 0.048(2) Uani 1 1 d . . . H22 H -0.1484 0.2861 0.1458 0.058 Uiso 1 1 calc R . . C23 C 0.2488(13) 0.1760(10) 0.0192(7) 0.051(2) Uani 1 1 d . . . H23A H 0.2029 0.1643 -0.0351 0.062 Uiso 1 1 calc R . . H23B H 0.3670 0.1351 0.0168 0.062 Uiso 1 1 calc R . . C24 C 0.2400(14) 0.3170(10) 0.0192(7) 0.053(2) Uani 1 1 d . . . H24A H 0.1229 0.3595 0.0172 0.063 Uiso 1 1 calc R . . H24B H 0.3091 0.3564 -0.0350 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.0364(2) 0.02634(19) 0.0320(2) -0.00589(12) -0.00260(13) -0.00703(12) P1 0.0390(12) 0.0392(12) 0.0485(14) -0.0093(10) -0.0046(10) -0.0029(9) N1 0.046(4) 0.040(4) 0.044(4) -0.014(3) -0.005(3) -0.007(3) N2 0.041(4) 0.035(4) 0.044(4) 0.000(3) -0.004(3) -0.007(3) N3 0.043(4) 0.031(3) 0.038(4) -0.008(3) -0.007(3) -0.006(3) N4 0.046(4) 0.036(4) 0.030(4) -0.007(3) 0.000(3) -0.009(3) F1 0.121(7) 0.153(9) 0.161(10) -0.103(8) 0.073(7) -0.052(7) F2 0.076(5) 0.077(5) 0.131(7) -0.029(5) -0.016(5) -0.034(4) F3 0.068(4) 0.068(4) 0.134(7) -0.015(4) -0.012(4) -0.030(4) F4 0.130(8) 0.111(7) 0.165(10) 0.055(7) -0.087(8) -0.025(6) F5 0.156(9) 0.104(7) 0.146(9) 0.048(6) -0.101(8) -0.036(6) F6 0.106(7) 0.142(8) 0.162(10) -0.101(8) 0.053(7) -0.018(6) C1 0.049(5) 0.042(5) 0.033(4) -0.011(4) -0.001(4) -0.022(4) C2 0.050(5) 0.061(6) 0.045(6) -0.007(5) 0.003(4) -0.021(5) C3 0.073(7) 0.073(8) 0.047(6) -0.008(5) 0.008(5) -0.037(6) C4 0.111(10) 0.057(7) 0.048(6) -0.002(5) 0.010(6) -0.049(7) C5 0.092(8) 0.040(5) 0.042(5) 0.003(4) -0.001(5) -0.025(5) C6 0.061(6) 0.033(4) 0.034(5) -0.011(4) -0.003(4) -0.010(4) C7 0.057(5) 0.033(4) 0.038(5) -0.005(4) -0.013(4) -0.011(4) C8 0.087(8) 0.032(5) 0.054(6) -0.003(4) -0.009(6) 0.002(5) C9 0.073(8) 0.060(7) 0.071(8) -0.011(6) -0.023(6) 0.010(6) C10 0.043(5) 0.046(5) 0.075(7) -0.018(5) -0.008(5) -0.003(4) C11 0.051(5) 0.032(4) 0.055(6) -0.004(4) -0.003(4) -0.008(4) C12 0.052(5) 0.036(4) 0.030(4) 0.000(3) 0.002(4) -0.021(4) C13 0.057(6) 0.050(5) 0.045(5) -0.008(4) -0.011(4) -0.012(4) C14 0.081(8) 0.083(8) 0.049(6) -0.013(6) -0.014(6) -0.038(7) C15 0.094(9) 0.087(9) 0.044(6) -0.027(6) 0.000(6) -0.051(8) C16 0.086(8) 0.047(6) 0.053(6) -0.023(5) 0.004(6) -0.017(5) C17 0.065(6) 0.034(4) 0.030(4) -0.006(3) -0.002(4) -0.016(4) C18 0.054(5) 0.030(4) 0.034(4) -0.005(3) 0.008(4) -0.010(4) C19 0.072(7) 0.042(5) 0.061(7) -0.018(5) 0.010(6) 0.003(5) C20 0.058(6) 0.046(6) 0.078(8) -0.015(5) 0.006(6) 0.010(5) C21 0.042(5) 0.050(6) 0.082(8) -0.013(5) -0.004(5) -0.001(4) C22 0.045(5) 0.045(5) 0.057(6) -0.014(4) -0.009(4) -0.002(4) C23 0.056(6) 0.066(6) 0.039(5) -0.023(5) 0.001(4) -0.016(5) C24 0.064(6) 0.052(6) 0.037(5) 0.006(4) -0.008(5) -0.012(5) _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 C12 2.007(9) . ? Ir1 C1 2.009(8) . ? Ir1 N3 2.042(7) . ? Ir1 N4 2.055(7) . ? Ir1 N2 2.197(7) . ? Ir1 N1 2.207(7) . ? P1 F6 1.522(8) . ? P1 F4 1.535(8) . ? P1 F5 1.569(8) . ? P1 F3 1.573(7) . ? P1 F1 1.575(8) . ? P1 F2 1.583(7) . ? N1 C23 1.479(12) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N2 C24 1.495(12) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N3 C11 1.349(12) . ? N3 C7 1.358(11) . ? N4 C22 1.345(12) . ? N4 C18 1.365(11) . ? C1 C2 1.385(13) . ? C1 C6 1.410(13) . ? C2 C3 1.364(14) . ? C2 H2 0.9300 . ? C3 C4 1.404(17) . ? C3 H3 0.9300 . ? C4 C5 1.355(17) . ? C4 H4 0.9300 . ? C5 C6 1.407(13) . ? C5 H5 0.9300 . ? C6 C7 1.472(13) . ? C7 C8 1.377(14) . ? C8 C9 1.382(17) . ? C8 H8 0.9300 . ? C9 C10 1.389(16) . ? C9 H9 0.9300 . ? C10 C11 1.361(13) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.400(13) . ? C12 C17 1.410(13) . ? C13 C14 1.398(14) . ? C13 H13 0.9300 . ? C14 C15 1.361(18) . ? C14 H14 0.9300 . ? C15 C16 1.365(17) . ? C15 H15 0.9300 . ? C16 C17 1.393(13) . ? C16 H16 0.9300 . ? C17 C18 1.453(13) . ? C18 C19 1.410(13) . ? C19 C20 1.383(17) . ? C19 H19 0.9300 . ? C20 C21 1.370(16) . ? C20 H20 0.9300 . ? C21 C22 1.360(13) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.490(14) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? 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 C12 Ir1 C1 91.9(3) . . ? C12 Ir1 N3 94.5(3) . . ? C1 Ir1 N3 80.7(3) . . ? C12 Ir1 N4 80.5(3) . . ? C1 Ir1 N4 94.5(3) . . ? N3 Ir1 N4 173.0(3) . . ? C12 Ir1 N2 94.8(3) . . ? C1 Ir1 N2 173.3(3) . . ? N3 Ir1 N2 99.0(3) . . ? N4 Ir1 N2 86.3(3) . . ? C12 Ir1 N1 174.2(3) . . ? C1 Ir1 N1 93.8(3) . . ? N3 Ir1 N1 86.4(3) . . ? N4 Ir1 N1 99.1(3) . . ? N2 Ir1 N1 79.5(3) . . ? F6 P1 F4 94.1(8) . . ? F6 P1 F5 88.2(7) . . ? F4 P1 F5 177.6(8) . . ? F6 P1 F3 91.9(5) . . ? F4 P1 F3 89.6(5) . . ? F5 P1 F3 89.7(5) . . ? F6 P1 F1 175.6(8) . . ? F4 P1 F1 90.3(8) . . ? F5 P1 F1 87.4(7) . . ? F3 P1 F1 88.7(5) . . ? F6 P1 F2 89.2(5) . . ? F4 P1 F2 92.1(5) . . ? F5 P1 F2 88.5(5) . . ? F3 P1 F2 177.8(5) . . ? F1 P1 F2 90.1(5) . . ? C23 N1 Ir1 108.1(5) . . ? C23 N1 H1A 110.1 . . ? Ir1 N1 H1A 110.1 . . ? C23 N1 H1B 110.1 . . ? Ir1 N1 H1B 110.1 . . ? H1A N1 H1B 108.4 . . ? C24 N2 Ir1 108.5(5) . . ? C24 N2 H2A 110.0 . . ? Ir1 N2 H2A 110.0 . . ? C24 N2 H2B 110.0 . . ? Ir1 N2 H2B 110.0 . . ? H2A N2 H2B 108.4 . . ? C11 N3 C7 117.7(8) . . ? C11 N3 Ir1 125.8(6) . . ? C7 N3 Ir1 116.4(6) . . ? C22 N4 C18 119.2(8) . . ? C22 N4 Ir1 125.9(6) . . ? C18 N4 Ir1 114.8(6) . . ? C2 C1 C6 116.9(8) . . ? C2 C1 Ir1 129.2(7) . . ? C6 C1 Ir1 113.8(6) . . ? C3 C2 C1 122.5(11) . . ? C3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? C2 C3 C4 119.4(11) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.7(10) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.3(11) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 121.1(9) . . ? C5 C6 C7 123.0(9) . . ? C1 C6 C7 115.9(8) . . ? N3 C7 C8 120.7(9) . . ? N3 C7 C6 113.1(8) . . ? C8 C7 C6 126.1(9) . . ? C7 C8 C9 121.0(10) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C8 C9 C10 117.8(10) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? C11 C10 C9 118.8(10) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? N3 C11 C10 123.9(9) . . ? N3 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? C13 C12 C17 117.1(8) . . ? C13 C12 Ir1 128.3(7) . . ? C17 C12 Ir1 114.5(6) . . ? C14 C13 C12 119.8(10) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 121.8(11) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C16 119.7(10) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 120.2(11) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 121.3(9) . . ? C16 C17 C18 123.7(9) . . ? C12 C17 C18 114.9(7) . . ? N4 C18 C19 119.1(9) . . ? N4 C18 C17 114.9(8) . . ? C19 C18 C17 126.0(9) . . ? C20 C19 C18 120.0(10) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 119.4(9) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C22 C21 C20 118.9(11) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? N4 C22 C21 123.4(9) . . ? N4 C22 H22 118.3 . . ? C21 C22 H22 118.3 . . ? N1 C23 C24 110.1(8) . . ? N1 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? N1 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.2 . . ? C23 C24 N2 108.6(7) . . ? C23 C24 H24A 110.0 . . ? N2 C24 H24A 110.0 . . ? C23 C24 H24B 110.0 . . ? N2 C24 H24B 110.0 . . ? H24A C24 H24B 108.3 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 5.086 _refine_diff_density_min -2.257 _refine_diff_density_rms 0.171 #===END data_(2b) _database_code_depnum_ccdc_archive 'CCDC 850265' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C24 H24 Ir N4), (F6 P), 2/3 (C3 H6 O) ' _chemical_formula_sum 'C26 H28 F6 Ir N4 O0.67 P' _chemical_formula_weight 744.36 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P-3c1 _symmetry_space_group_name_Hall '-P 3 2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' _cell_length_a 21.494(5) _cell_length_b 21.494(5) _cell_length_c 10.380(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4153(2) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3655 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 24.19 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.786 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2180 _exptl_absorpt_coefficient_mu 4.946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7557 _exptl_absorpt_correction_T_max 0.9522 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17861 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.82 _reflns_number_total 2971 _reflns_number_gt 2286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius X8 APEX' _computing_cell_refinement 'Bruker-Nonius X8 APEX' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0283P)^2^+0.9592P] 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 2971 _refine_ls_number_parameters 196 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.013 _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 Ir Ir 0.313153(12) 1.0000 0.2500 0.03306(10) Uani 1 2 d S . . N1 N 0.25572(19) 1.0440(2) 0.1404(3) 0.0448(10) Uani 1 1 d . . . H1A H 0.2751 1.0912 0.1572 0.054 Uiso 1 1 calc R . . H1B H 0.2598 1.0386 0.0554 0.054 Uiso 1 1 calc R . . N3 N 0.35878(19) 1.0781(2) 0.3895(3) 0.0382(9) Uani 1 1 d . . . C1 C 0.3569(2) 0.9558(2) 0.3615(4) 0.0365(10) Uani 1 1 d . . . C2 C 0.3581(2) 0.8919(2) 0.3427(4) 0.0413(11) Uani 1 1 d . . . H2 H 0.3387 0.8658 0.2674 0.050 Uiso 1 1 calc R . . C3 C 0.3871(3) 0.8666(3) 0.4326(5) 0.0535(13) Uani 1 1 d . . . H3 H 0.3871 0.8239 0.4173 0.064 Uiso 1 1 calc R . . C4 C 0.4163(3) 0.9042(3) 0.5458(5) 0.0617(15) Uani 1 1 d . . . H4 H 0.4343 0.8862 0.6079 0.074 Uiso 1 1 calc R . . C5 C 0.4183(3) 0.9680(3) 0.5649(4) 0.0525(13) Uani 1 1 d . . . H5 H 0.4395 0.9943 0.6393 0.063 Uiso 1 1 calc R . . C6 C 0.3893(2) 0.9943(2) 0.4752(4) 0.0399(11) Uani 1 1 d . . . C7 C 0.3922(2) 1.0633(3) 0.4861(4) 0.0410(11) Uani 1 1 d . . . C8 C 0.4289(3) 1.1151(3) 0.5806(4) 0.0547(14) Uani 1 1 d . . . H8 H 0.4519 1.1054 0.6471 0.066 Uiso 1 1 calc R . . C9 C 0.4316(3) 1.1804(3) 0.5763(5) 0.0604(15) Uani 1 1 d . . . H9 H 0.4560 1.2147 0.6397 0.072 Uiso 1 1 calc R . . C10 C 0.3981(3) 1.1944(3) 0.4780(5) 0.0535(13) Uani 1 1 d . . . H10 H 0.3997 1.2384 0.4727 0.064 Uiso 1 1 calc R . . C11 C 0.3621(3) 1.1423(3) 0.3874(4) 0.0464(12) Uani 1 1 d . . . H11 H 0.3387 1.1516 0.3212 0.056 Uiso 1 1 calc R . . C12 C 0.1789(2) 1.0053(3) 0.1782(4) 0.0533(13) Uani 1 1 d . . . H12A H 0.1541 0.9591 0.1351 0.064 Uiso 1 1 calc R . . H12B H 0.1565 1.0330 0.1527 0.064 Uiso 1 1 calc R . . C20 C 0.3333 0.6667 0.209(2) 0.154(6) Uiso 1 3 d SD . . C21A C 0.2871(13) 0.6977(13) 0.157(2) 0.095(7) Uiso 0.33 1 d PD . . C21B C 0.3251(18) 0.7236(15) 0.131(3) 0.146(13) Uiso 0.33 1 d PD . . P1 P 0.77859(9) 0.0000 0.2500 0.0481(5) Uani 1 2 d S . . F3 F 0.81090(19) 0.06499(18) 0.1505(3) 0.0845(10) Uani 1 1 d . . . F2A F 0.757(3) 0.0409(16) 0.341(2) 0.126(10) Uani 0.49(8) 1 d P . . F2B F 0.7367(14) 0.0340(13) 0.322(2) 0.104(6) Uani 0.51(8) 1 d P . . F1A F 0.8488(12) 0.025(3) 0.314(4) 0.123(10) Uani 0.49(8) 1 d P . . F1B F 0.8462(14) 0.0486(17) 0.3428(19) 0.114(8) Uani 0.51(8) 1 d P . . O1 O 0.3333 0.6667 0.317(2) 0.304(10) Uiso 1 3 d S . . 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 Ir 0.03365(14) 0.03484(17) 0.03109(12) -0.00187(10) -0.00094(5) 0.01742(8) N1 0.045(3) 0.048(3) 0.047(2) -0.0030(18) -0.0062(18) 0.027(2) N3 0.034(2) 0.040(2) 0.0360(18) -0.0030(16) 0.0035(16) 0.0155(19) C1 0.030(3) 0.039(3) 0.037(2) 0.0027(19) 0.0060(19) 0.015(2) C2 0.037(3) 0.044(3) 0.043(2) 0.005(2) 0.003(2) 0.020(2) C3 0.056(4) 0.053(3) 0.063(3) 0.010(3) 0.006(3) 0.036(3) C4 0.062(4) 0.074(4) 0.057(3) 0.019(3) -0.005(3) 0.040(3) C5 0.056(3) 0.060(4) 0.043(3) 0.000(2) -0.010(2) 0.029(3) C6 0.036(3) 0.048(3) 0.034(2) 0.001(2) 0.0000(19) 0.020(2) C7 0.037(3) 0.048(3) 0.033(2) -0.003(2) 0.0019(19) 0.018(3) C8 0.055(4) 0.064(4) 0.043(3) -0.008(2) -0.011(2) 0.028(3) C9 0.060(4) 0.058(4) 0.056(3) -0.020(3) -0.008(3) 0.024(3) C10 0.056(3) 0.043(3) 0.060(3) -0.013(2) 0.001(3) 0.023(3) C11 0.047(3) 0.044(3) 0.051(3) -0.010(2) -0.004(2) 0.025(3) C12 0.039(3) 0.057(3) 0.067(3) 0.001(3) -0.009(2) 0.026(3) P1 0.0557(10) 0.0397(11) 0.0436(9) 0.0004(8) 0.0002(4) 0.0198(6) F3 0.086(3) 0.072(2) 0.087(2) 0.0372(19) 0.0220(19) 0.033(2) F2A 0.23(3) 0.113(12) 0.067(8) -0.023(9) 0.021(13) 0.111(16) F2B 0.107(12) 0.100(11) 0.140(16) 0.045(11) 0.070(10) 0.077(8) F1A 0.064(8) 0.10(2) 0.158(19) 0.023(14) -0.062(10) 0.007(8) F1B 0.093(10) 0.089(13) 0.070(9) -0.005(7) -0.022(7) -0.023(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 Ir C1 2.004(5) 5_675 ? Ir C1 2.004(5) . ? Ir N3 2.057(3) 5_675 ? Ir N3 2.057(3) . ? Ir N1 2.209(4) . ? Ir N1 2.209(4) 5_675 ? N1 C12 1.483(5) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N3 C11 1.345(6) . ? N3 C7 1.361(5) . ? C1 C2 1.401(6) . ? C1 C6 1.409(5) . ? C2 C3 1.377(6) . ? C2 H2 0.9300 . ? C3 C4 1.386(7) . ? C3 H3 0.9300 . ? C4 C5 1.364(7) . ? C4 H4 0.9300 . ? C5 C6 1.389(6) . ? C5 H5 0.9300 . ? C6 C7 1.458(6) . ? C7 C8 1.394(6) . ? C8 C9 1.378(7) . ? C8 H8 0.9300 . ? C9 C10 1.367(7) . ? C9 H9 0.9300 . ? C10 C11 1.368(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C12 1.504(9) 5_675 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C20 O1 1.12(3) . ? C20 C21A 1.542(15) . ? C20 C21A 1.542(16) 3_565 ? C20 C21A 1.542(15) 2_665 ? C20 C21B 1.549(16) . ? C20 C21B 1.549(17) 2_665 ? C20 C21B 1.549(17) 3_565 ? C21A C21B 0.77(4) . ? C21A C21B 1.98(3) 2_665 ? C21B C21A 1.98(3) 3_565 ? P1 F1A 1.48(2) . ? P1 F1A 1.48(2) 5 ? P1 F2A 1.51(2) 5 ? P1 F2A 1.51(2) . ? P1 F3 1.590(3) . ? P1 F3 1.590(3) 5 ? P1 F2B 1.60(2) 5 ? P1 F2B 1.60(2) . ? P1 F1B 1.617(19) 5 ? P1 F1B 1.617(19) . ? F1A F1B 0.61(6) . ? F1A F1A 1.63(12) 5 ? 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 Ir C1 90.2(2) 5_675 . ? C1 Ir N3 80.51(16) 5_675 5_675 ? C1 Ir N3 93.90(16) . 5_675 ? C1 Ir N3 93.90(16) 5_675 . ? C1 Ir N3 80.51(16) . . ? N3 Ir N3 172.1(2) 5_675 . ? C1 Ir N1 95.51(15) 5_675 . ? C1 Ir N1 174.27(15) . . ? N3 Ir N1 87.29(14) 5_675 . ? N3 Ir N1 98.82(14) . . ? C1 Ir N1 174.27(15) 5_675 5_675 ? C1 Ir N1 95.51(15) . 5_675 ? N3 Ir N1 98.82(15) 5_675 5_675 ? N3 Ir N1 87.29(14) . 5_675 ? N1 Ir N1 78.76(19) . 5_675 ? C12 N1 Ir 109.2(3) . . ? C12 N1 H1A 109.8 . . ? Ir N1 H1A 109.8 . . ? C12 N1 H1B 109.8 . . ? Ir N1 H1B 109.8 . . ? H1A N1 H1B 108.3 . . ? C11 N3 C7 119.2(4) . . ? C11 N3 Ir 125.8(3) . . ? C7 N3 Ir 114.8(3) . . ? C2 C1 C6 116.5(4) . . ? C2 C1 Ir 128.8(3) . . ? C6 C1 Ir 114.6(3) . . ? C3 C2 C1 121.8(4) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 120.4(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.2(5) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.1(5) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 120.9(4) . . ? C5 C6 C7 124.2(4) . . ? C1 C6 C7 114.8(4) . . ? N3 C7 C8 119.1(4) . . ? N3 C7 C6 114.9(4) . . ? C8 C7 C6 125.9(4) . . ? C9 C8 C7 120.6(5) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 119.4(5) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 118.5(5) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? N3 C11 C10 123.2(5) . . ? N3 C11 H11 118.4 . . ? C10 C11 H11 118.4 . . ? N1 C12 C12 109.0(3) . 5_675 ? N1 C12 H12A 109.9 . . ? C12 C12 H12A 109.9 5_675 . ? N1 C12 H12B 109.9 . . ? C12 C12 H12B 109.9 5_675 . ? H12A C12 H12B 108.3 . . ? O1 C20 C21A 110.3(12) . . ? O1 C20 C21A 110.3(12) . 3_565 ? C21A C20 C21A 108.6(13) . 3_565 ? O1 C20 C21A 110.3(12) . 2_665 ? C21A C20 C21A 108.6(13) . 2_665 ? C21A C20 C21A 108.6(13) 3_565 2_665 ? O1 C20 C21B 121.5(15) . . ? C21A C20 C21B 29.0(13) . . ? C21A C20 C21B 79.7(15) 3_565 . ? C21A C20 C21B 121(2) 2_665 . ? O1 C20 C21B 121.5(15) . 2_665 ? C21A C20 C21B 79.7(15) . 2_665 ? C21A C20 C21B 121(2) 3_565 2_665 ? C21A C20 C21B 29.0(13) 2_665 2_665 ? C21B C20 C21B 95(2) . 2_665 ? O1 C20 C21B 121.5(15) . 3_565 ? C21A C20 C21B 121(2) . 3_565 ? C21A C20 C21B 29.0(13) 3_565 3_565 ? C21A C20 C21B 79.7(15) 2_665 3_565 ? C21B C20 C21B 95(2) . 3_565 ? C21B C20 C21B 95(2) 2_665 3_565 ? C21B C21A C20 76.0(12) . . ? C21B C21A C21B 103(3) . 2_665 ? C20 C21A C21B 50.3(8) . 2_665 ? C21A C21B C20 75.0(12) . . ? C21A C21B C21A 125.0(14) . 3_565 ? C20 C21B C21A 50.0(8) . 3_565 ? F1A P1 F1A 67(5) . 5 ? F1A P1 F2A 160(5) . 5 ? F1A P1 F2A 93.1(15) 5 5 ? F1A P1 F2A 93.1(15) . . ? F1A P1 F2A 160(5) 5 . ? F2A P1 F2A 107(4) 5 . ? F1A P1 F3 92.8(10) . . ? F1A P1 F3 87.4(10) 5 . ? F2A P1 F3 88.7(11) 5 . ? F2A P1 F3 91.1(11) . . ? F1A P1 F3 87.4(10) . 5 ? F1A P1 F3 92.8(10) 5 5 ? F2A P1 F3 91.1(11) 5 5 ? F2A P1 F3 88.7(11) . 5 ? F3 P1 F3 179.7(3) . 5 ? F1A P1 F2B 175(3) . 5 ? F1A P1 F2B 109(2) 5 5 ? F2A P1 F2B 16(2) 5 5 ? F2A P1 F2B 91(3) . 5 ? F3 P1 F2B 89.6(8) . 5 ? F3 P1 F2B 90.1(9) 5 5 ? F1A P1 F2B 109(2) . . ? F1A P1 F2B 175(3) 5 . ? F2A P1 F2B 91(3) 5 . ? F2A P1 F2B 16(2) . . ? F3 P1 F2B 90.1(8) . . ? F3 P1 F2B 89.6(8) 5 . ? F2B P1 F2B 76(2) 5 . ? F1A P1 F1B 88(4) . 5 ? F1A P1 F1B 22(2) 5 5 ? F2A P1 F1B 71.8(16) 5 5 ? F2A P1 F1B 176(2) . 5 ? F3 P1 F1B 92.3(10) . 5 ? F3 P1 F1B 87.9(10) 5 5 ? F2B P1 F1B 87.4(12) 5 5 ? F2B P1 F1B 163(2) . 5 ? F1A P1 F1B 22(2) . . ? F1A P1 F1B 88(4) 5 . ? F2A P1 F1B 176(2) 5 . ? F2A P1 F1B 71.8(16) . . ? F3 P1 F1B 87.9(10) . . ? F3 P1 F1B 92.3(10) 5 . ? F2B P1 F1B 163(2) 5 . ? F2B P1 F1B 87.4(12) . . ? F1B P1 F1B 110(3) 5 . ? F1B F1A P1 92(4) . . ? F1B F1A F1A 145(5) . 5 ? P1 F1A F1A 57(3) . 5 ? F1A F1B P1 66(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.82 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.382 _refine_diff_density_min -0.720 _refine_diff_density_rms 0.113 #===END data_(3a) _database_code_depnum_ccdc_archive 'CCDC 850266' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cl Ir N4, 3(H2 O)' _chemical_formula_sum 'C24 H30 Cl Ir N4 O3' _chemical_formula_weight 650.17 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R3c _symmetry_space_group_name_Hall 'R 3 -2"c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' _cell_length_a 29.092(7) _cell_length_b 29.092(7) _cell_length_c 15.193(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 11135(5) _cell_formula_units_Z 18 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8999 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 27.14 _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5760 _exptl_absorpt_coefficient_mu 5.536 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9467 _exptl_absorpt_correction_T_max 0.9675 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35693 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.11 _reflns_number_total 5450 _reflns_number_gt 5291 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0316P)^2^+4.2759P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(7) _refine_ls_number_reflns 5450 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0198 _refine_ls_R_factor_gt 0.0174 _refine_ls_wR_factor_ref 0.0609 _refine_ls_wR_factor_gt 0.0443 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_restrained_S_all 1.203 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.338336(6) 0.481360(6) 0.84162(3) 0.02677(5) Uani 1 1 d . C . N1 N 0.36969(18) 0.55636(19) 0.9152(4) 0.0378(11) Uani 1 1 d . . . H1A H 0.3534 0.5503 0.9678 0.045 Uiso 1 1 calc R A 1 H1B H 0.4047 0.5702 0.9247 0.045 Uiso 1 1 calc R A 1 N2 N 0.30188(19) 0.52142(19) 0.7714(4) 0.0420(12) Uani 1 1 d . . . H2A H 0.3177 0.5326 0.7186 0.050 Uiso 1 1 calc R B 1 H2B H 0.2673 0.4981 0.7620 0.050 Uiso 1 1 calc R B 1 N3 N 0.28296(17) 0.44508(16) 0.9385(3) 0.0307(9) Uani 1 1 d . . . N4 N 0.39388(18) 0.50914(16) 0.7427(3) 0.0320(10) Uani 1 1 d . . . C1 C 0.3740(2) 0.45074(19) 0.9128(4) 0.0302(11) Uani 1 1 d . . . C2 C 0.4251(2) 0.4580(2) 0.9038(3) 0.0363(11) Uani 1 1 d . C . H2 H 0.4468 0.4801 0.8592 0.044 Uiso 1 1 calc R . . C3 C 0.4444(2) 0.4339(2) 0.9584(4) 0.0454(12) Uani 1 1 d . . . H3 H 0.4787 0.4400 0.9501 0.055 Uiso 1 1 calc R C . C4 C 0.4135(2) 0.4007(2) 1.0251(4) 0.0506(15) Uani 1 1 d . C . H4 H 0.4263 0.3836 1.0606 0.061 Uiso 1 1 calc R . . C5 C 0.3627(2) 0.3931(2) 1.0388(4) 0.0452(12) Uani 1 1 d . . . H5 H 0.3417 0.3712 1.0841 0.054 Uiso 1 1 calc R C . C6 C 0.34385(18) 0.41831(18) 0.9845(3) 0.0339(10) Uani 1 1 d . C . C7 C 0.29260(19) 0.41501(19) 0.9967(3) 0.0339(10) Uani 1 1 d . C . C8 C 0.2562(2) 0.3861(2) 1.0607(4) 0.0503(14) Uani 1 1 d . . . H8 H 0.2626 0.3648 1.0989 0.060 Uiso 1 1 calc R C . C9 C 0.2100(2) 0.3885(3) 1.0685(4) 0.0583(17) Uani 1 1 d . C . H9 H 0.1854 0.3694 1.1122 0.070 Uiso 1 1 calc R . . C10 C 0.2008(2) 0.4192(2) 1.0114(4) 0.0489(14) Uani 1 1 d . . . H10 H 0.1702 0.4216 1.0160 0.059 Uiso 1 1 calc R C . C11 C 0.2380(2) 0.4468(2) 0.9465(4) 0.0403(11) Uani 1 1 d . C . H11 H 0.2314 0.4672 0.9069 0.048 Uiso 1 1 calc R . . C12 C 0.30640(19) 0.4177(2) 0.7619(4) 0.0326(12) Uani 1 1 d . . . C13 C 0.2613(2) 0.36888(19) 0.7745(4) 0.0428(12) Uani 1 1 d . C . H13 H 0.2430 0.3623 0.8274 0.051 Uiso 1 1 calc R . . C14 C 0.2425(2) 0.3293(2) 0.7107(4) 0.0504(13) Uani 1 1 d . . . H14 H 0.2118 0.2970 0.7209 0.060 Uiso 1 1 calc R C . C15 C 0.2697(3) 0.3383(3) 0.6317(4) 0.0537(16) Uani 1 1 d . C . H15 H 0.2575 0.3119 0.5889 0.064 Uiso 1 1 calc R . . C16 C 0.3145(2) 0.3862(2) 0.6172(4) 0.0472(13) Uani 1 1 d . . . H16 H 0.3327 0.3926 0.5641 0.057 Uiso 1 1 calc R C . C17 C 0.3328(2) 0.42516(19) 0.6820(3) 0.0362(10) Uani 1 1 d . C . C18 C 0.3812(2) 0.4766(2) 0.6718(3) 0.0348(10) Uani 1 1 d . C . C19 C 0.4149(2) 0.4932(3) 0.5996(4) 0.0501(14) Uani 1 1 d . . . H19 H 0.4063 0.4715 0.5503 0.060 Uiso 1 1 calc R C . C20 C 0.4610(2) 0.5416(3) 0.6004(4) 0.0569(16) Uani 1 1 d . C . H20 H 0.4831 0.5528 0.5514 0.068 Uiso 1 1 calc R . . C22 C 0.4389(2) 0.5555(2) 0.7427(3) 0.0427(11) Uani 1 1 d . C . H22A H 0.4469 0.5772 0.7921 0.051 Uiso 1 1 calc R . . C21 C 0.4740(2) 0.5731(3) 0.6736(4) 0.0530(15) Uani 1 1 d . . . H21A H 0.5057 0.6054 0.6765 0.064 Uiso 1 1 calc R C . C23 C 0.3601(5) 0.5948(4) 0.8625(8) 0.045(3) Uiso 0.59(2) 1 d P C 1 H23A H 0.3623 0.6225 0.9009 0.054 Uiso 0.59(2) 1 calc PR C 1 H23B H 0.3871 0.6114 0.8175 0.054 Uiso 0.59(2) 1 calc PR C 1 C24 C 0.3068(5) 0.5665(4) 0.8208(7) 0.044(3) Uiso 0.59(2) 1 d P C 1 H24A H 0.2794 0.5543 0.8656 0.053 Uiso 0.59(2) 1 calc PR C 1 H24B H 0.3023 0.5903 0.7816 0.053 Uiso 0.59(2) 1 calc PR C 1 C23A C 0.3381(9) 0.5844(8) 0.8942(15) 0.062(5) Uiso 0.41(2) 1 d P C 2 H23C H 0.3040 0.5670 0.9237 0.075 Uiso 0.41(2) 1 calc PR C 2 H23D H 0.3576 0.6213 0.9123 0.075 Uiso 0.41(2) 1 calc PR C 2 C24A C 0.3313(8) 0.5799(7) 0.7975(12) 0.053(5) Uiso 0.41(2) 1 d P C 2 H24C H 0.3658 0.5979 0.7691 0.063 Uiso 0.41(2) 1 calc PR C 2 H24D H 0.3114 0.5966 0.7785 0.063 Uiso 0.41(2) 1 calc PR C 2 Cl1 Cl 0.49315(7) 0.65367(6) 0.91708(12) 0.0634(4) Uani 1 1 d . . . O1W O 0.3301(2) 0.5674(2) 0.1019(4) 0.0770(16) Uani 1 1 d . . . O2W O 0.23423(19) 0.5696(2) 0.0842(4) 0.0720(14) Uani 1 1 d . . . O3W O 0.2984(2) 0.4841(2) 0.2336(4) 0.0763(14) 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 0.02923(9) 0.02845(9) 0.02193(8) 0.00188(6) 0.00366(6) 0.01389(7) N1 0.040(2) 0.039(3) 0.033(3) -0.001(2) 0.0049(18) 0.0191(19) N2 0.044(2) 0.048(3) 0.037(3) 0.011(2) 0.002(2) 0.025(2) N3 0.029(2) 0.0330(19) 0.028(2) 0.0038(16) 0.0025(16) 0.0142(17) N4 0.032(2) 0.038(2) 0.027(2) 0.0031(16) 0.0049(17) 0.0181(18) C1 0.037(2) 0.032(2) 0.023(2) -0.0052(18) 0.0001(19) 0.018(2) C2 0.038(3) 0.045(3) 0.034(3) -0.007(2) 0.002(2) 0.026(2) C3 0.045(3) 0.058(3) 0.047(3) -0.012(3) -0.005(2) 0.036(3) C4 0.062(4) 0.054(3) 0.051(4) -0.002(3) -0.014(3) 0.040(3) C5 0.052(3) 0.046(3) 0.041(3) 0.003(2) -0.005(2) 0.027(3) C6 0.033(2) 0.033(2) 0.032(2) -0.0009(19) -0.0048(19) 0.0133(19) C7 0.037(2) 0.035(2) 0.026(2) 0.0021(19) 0.0018(19) 0.016(2) C8 0.049(3) 0.055(3) 0.043(3) 0.024(3) 0.012(2) 0.023(3) C9 0.046(3) 0.075(4) 0.048(3) 0.031(3) 0.020(3) 0.026(3) C10 0.035(3) 0.066(4) 0.046(3) 0.015(3) 0.011(2) 0.025(3) C11 0.036(3) 0.046(3) 0.042(3) 0.010(2) 0.007(2) 0.022(2) C12 0.035(2) 0.031(3) 0.030(3) 0.000(2) -0.0046(19) 0.016(2) C13 0.050(3) 0.035(3) 0.041(3) 0.001(2) -0.005(2) 0.020(2) C14 0.054(3) 0.033(3) 0.057(3) -0.006(3) -0.017(3) 0.017(2) C15 0.070(4) 0.054(4) 0.046(3) -0.024(3) -0.023(3) 0.038(3) C16 0.056(3) 0.055(3) 0.037(3) -0.014(2) -0.009(2) 0.032(3) C17 0.045(3) 0.041(3) 0.029(2) -0.005(2) -0.006(2) 0.027(2) C18 0.043(2) 0.048(3) 0.024(2) 0.003(2) 0.0019(18) 0.031(2) C19 0.059(3) 0.069(4) 0.029(2) 0.000(3) 0.009(2) 0.037(3) C20 0.051(3) 0.071(4) 0.048(3) 0.012(3) 0.028(3) 0.030(3) C22 0.043(3) 0.042(3) 0.037(3) 0.004(2) 0.011(2) 0.017(2) C21 0.040(3) 0.054(3) 0.054(4) 0.006(3) 0.019(3) 0.016(3) Cl1 0.0624(10) 0.0476(8) 0.0640(10) -0.0052(7) 0.0004(8) 0.0153(7) O1W 0.064(3) 0.094(4) 0.070(4) 0.010(3) 0.016(3) 0.037(3) O2W 0.074(3) 0.083(3) 0.065(3) 0.009(3) -0.009(3) 0.044(3) O3W 0.062(3) 0.080(3) 0.087(4) -0.002(3) 0.001(3) 0.035(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 C1 1.990(6) . ? Ir1 C12 2.009(6) . ? Ir1 N3 2.043(4) . ? Ir1 N4 2.054(5) . ? Ir1 N1 2.203(5) . ? Ir1 N2 2.204(5) . ? N1 C23 1.512(11) . ? N1 C23A 1.536(17) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N2 C24 1.455(11) . ? N2 C24A 1.526(16) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N3 C11 1.340(6) . ? N3 C7 1.368(6) . ? N4 C22 1.329(7) . ? N4 C18 1.358(6) . ? C1 C2 1.398(7) . ? C1 C6 1.421(7) . ? C2 C3 1.377(7) . ? C2 H2 0.9300 . ? C3 C4 1.378(9) . ? C3 H3 0.9300 . ? C4 C5 1.395(8) . ? C4 H4 0.9300 . ? C5 C6 1.387(7) . ? C5 H5 0.9300 . ? C6 C7 1.457(6) . ? C7 C8 1.373(7) . ? C8 C9 1.388(8) . ? C8 H8 0.9300 . ? C9 C10 1.363(8) . ? C9 H9 0.9300 . ? C10 C11 1.385(7) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.382(7) . ? C12 C17 1.395(8) . ? C13 C14 1.391(7) . ? C13 H13 0.9300 . ? C14 C15 1.388(9) . ? C14 H14 0.9300 . ? C15 C16 1.370(9) . ? C15 H15 0.9300 . ? C16 C17 1.391(7) . ? C16 H16 0.9300 . ? C17 C18 1.462(7) . ? C18 C19 1.387(7) . ? C19 C20 1.375(9) . ? C19 H19 0.9300 . ? C20 C21 1.370(9) . ? C20 H20 0.9300 . ? C22 C21 1.374(7) . ? C22 H22A 0.9300 . ? C21 H21A 0.9300 . ? C23 C24 1.486(14) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C23A C24A 1.48(3) . ? C23A H23C 0.9700 . ? C23A H23D 0.9700 . ? C24A H24C 0.9700 . ? C24A H24D 0.9700 . ? 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 Ir1 C12 91.09(17) . . ? C1 Ir1 N3 80.24(17) . . ? C12 Ir1 N3 94.36(19) . . ? C1 Ir1 N4 95.2(2) . . ? C12 Ir1 N4 80.3(2) . . ? N3 Ir1 N4 172.96(15) . . ? C1 Ir1 N1 96.7(2) . . ? C12 Ir1 N1 172.0(2) . . ? N3 Ir1 N1 88.58(17) . . ? N4 Ir1 N1 97.30(18) . . ? C1 Ir1 N2 174.7(2) . . ? C12 Ir1 N2 94.2(2) . . ? N3 Ir1 N2 99.1(2) . . ? N4 Ir1 N2 85.96(17) . . ? N1 Ir1 N2 78.02(15) . . ? C23 N1 C23A 27.8(8) . . ? C23 N1 Ir1 109.1(5) . . ? C23A N1 Ir1 111.0(8) . . ? C23 N1 H1A 109.9 . . ? C23A N1 H1A 83.8 . . ? Ir1 N1 H1A 109.9 . . ? C23 N1 H1B 109.9 . . ? C23A N1 H1B 129.7 . . ? Ir1 N1 H1B 109.9 . . ? H1A N1 H1B 108.3 . . ? C24 N2 C24A 27.6(7) . . ? C24 N2 Ir1 111.8(5) . . ? C24A N2 Ir1 108.2(7) . . ? C24 N2 H2A 109.3 . . ? C24A N2 H2A 85.8 . . ? Ir1 N2 H2A 109.3 . . ? C24 N2 H2B 109.3 . . ? C24A N2 H2B 132.4 . . ? Ir1 N2 H2B 109.3 . . ? H2A N2 H2B 107.9 . . ? C11 N3 C7 118.8(4) . . ? C11 N3 Ir1 125.4(4) . . ? C7 N3 Ir1 115.8(3) . . ? C22 N4 C18 119.7(5) . . ? C22 N4 Ir1 125.5(4) . . ? C18 N4 Ir1 114.8(3) . . ? C2 C1 C6 115.6(5) . . ? C2 C1 Ir1 129.1(4) . . ? C6 C1 Ir1 115.3(4) . . ? C3 C2 C1 122.6(5) . . ? C3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? C2 C3 C4 120.6(5) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.4(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 119.6(5) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 122.1(5) . . ? C5 C6 C7 123.5(5) . . ? C1 C6 C7 114.4(4) . . ? N3 C7 C8 120.6(5) . . ? N3 C7 C6 113.9(4) . . ? C8 C7 C6 125.4(5) . . ? C7 C8 C9 119.8(5) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 119.5(5) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 118.7(5) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? N3 C11 C10 122.5(5) . . ? N3 C11 H11 118.7 . . ? C10 C11 H11 118.7 . . ? C13 C12 C17 116.5(5) . . ? C13 C12 Ir1 128.9(5) . . ? C17 C12 Ir1 114.6(4) . . ? C12 C13 C14 122.2(6) . . ? C12 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C15 C14 C13 119.7(6) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 119.6(5) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 119.8(6) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 122.2(5) . . ? C16 C17 C18 122.6(5) . . ? C12 C17 C18 115.2(4) . . ? N4 C18 C19 119.1(5) . . ? N4 C18 C17 114.6(4) . . ? C19 C18 C17 126.3(5) . . ? C20 C19 C18 120.5(5) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 119.7(5) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? N4 C22 C21 123.3(5) . . ? N4 C22 H22A 118.3 . . ? C21 C22 H22A 118.3 . . ? C20 C21 C22 117.7(5) . . ? C20 C21 H21A 121.1 . . ? C22 C21 H21A 121.1 . . ? C24 C23 N1 110.1(9) . . ? C24 C23 H23A 109.6 . . ? N1 C23 H23A 109.6 . . ? C24 C23 H23B 109.6 . . ? N1 C23 H23B 109.6 . . ? H23A C23 H23B 108.2 . . ? N2 C24 C23 109.0(9) . . ? N2 C24 H24A 109.9 . . ? C23 C24 H24A 109.9 . . ? N2 C24 H24B 109.9 . . ? C23 C24 H24B 109.9 . . ? H24A C24 H24B 108.3 . . ? C24A C23A N1 104.3(16) . . ? C24A C23A H23C 110.9 . . ? N1 C23A H23C 110.9 . . ? C24A C23A H23D 110.9 . . ? N1 C23A H23D 110.9 . . ? H23C C23A H23D 108.9 . . ? C23A C24A N2 109.4(15) . . ? C23A C24A H24C 109.8 . . ? N2 C24A H24C 109.8 . . ? C23A C24A H24D 109.8 . . ? N2 C24A H24D 109.8 . . ? H24C C24A H24D 108.2 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.11 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.714 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.139 #===END data_(3b) _database_code_depnum_ccdc_archive 'CCDC 850267' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cl Ir N4' _chemical_formula_sum 'C24 H24 Cl Ir N4' _chemical_formula_weight 596.12 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.534(3) _cell_length_b 22.985(3) _cell_length_c 10.2524(14) _cell_angle_alpha 90.00 _cell_angle_beta 109.164(8) _cell_angle_gamma 90.00 _cell_volume 3012.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9966 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 24.66 _exptl_crystal_description rombohedral _exptl_crystal_colour yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 4.534 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7726 _exptl_absorpt_correction_T_max 0.9148 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 80956 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.12 _reflns_number_total 6634 _reflns_number_gt 6273 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius X8 APEX' _computing_cell_refinement 'Bruker-Nonius X8 APEX' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0270P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(5) _refine_ls_number_reflns 6634 _refine_ls_number_parameters 271 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0201 _refine_ls_R_factor_gt 0.0182 _refine_ls_wR_factor_ref 0.0474 _refine_ls_wR_factor_gt 0.0470 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.005 _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 0.250985(18) 0.647008(4) 0.250885(19) 0.03644(4) Uani 1 1 d . . . Cl1 Cl 0.39403(8) 0.77406(5) 0.65861(11) 0.0633(3) Uani 1 1 d . . . N1 N 0.2767(2) 0.73679(13) 0.3358(3) 0.0478(7) Uani 1 1 d . . . H1A H 0.3292 0.7370 0.4171 0.057 Uiso 1 1 calc R . . H1B H 0.2942 0.7605 0.2771 0.057 Uiso 1 1 calc R . . N3 N 0.1889(2) 0.68514(12) 0.0574(3) 0.0420(6) Uani 1 1 d . . . N2 N 0.1171(4) 0.65739(15) 0.3248(6) 0.0430(10) Uani 1 1 d . . . H2A H 0.0585 0.6631 0.2525 0.052 Uiso 1 1 calc R . . H2B H 0.1088 0.6248 0.3688 0.052 Uiso 1 1 calc R . . N4 N 0.3286(2) 0.60206(12) 0.4302(3) 0.0421(6) Uani 1 1 d . . . C1 C 0.3785(6) 0.64099(15) 0.1871(7) 0.0399(11) Uani 1 1 d . . . C2 C 0.4766(3) 0.61811(16) 0.2547(4) 0.0490(8) Uani 1 1 d . . . H2 H 0.4912 0.6030 0.3432 0.059 Uiso 1 1 calc R . . C3 C 0.5531(3) 0.61737(19) 0.1932(5) 0.0578(10) Uani 1 1 d . . . H3 H 0.6176 0.6008 0.2409 0.069 Uiso 1 1 calc R . . C4 C 0.5376(4) 0.64041(18) 0.0623(6) 0.0625(12) Uani 1 1 d . . . H4 H 0.5907 0.6395 0.0233 0.075 Uiso 1 1 calc R . . C5 C 0.4401(3) 0.66497(19) -0.0092(5) 0.0549(9) Uani 1 1 d . . . H5 H 0.4277 0.6808 -0.0966 0.066 Uiso 1 1 calc R . . C6 C 0.3611(3) 0.66558(16) 0.0517(4) 0.0420(7) Uani 1 1 d . . . C7 C 0.2581(3) 0.68907(14) -0.0179(3) 0.0430(7) Uani 1 1 d . . . C8 C 0.2229(4) 0.71426(18) -0.1504(4) 0.0612(10) Uani 1 1 d . . . H8 H 0.2683 0.7160 -0.2015 0.073 Uiso 1 1 calc R . . C9 C 0.1250(4) 0.7360(2) -0.2057(5) 0.0702(12) Uani 1 1 d . . . H9 H 0.1031 0.7530 -0.2928 0.084 Uiso 1 1 calc R . . C10 C 0.0576(4) 0.7318(2) -0.1269(5) 0.0770(14) Uani 1 1 d . . . H10 H -0.0104 0.7459 -0.1623 0.092 Uiso 1 1 calc R . . C11 C 0.0918(3) 0.70686(19) 0.0025(4) 0.0599(10) Uani 1 1 d . . . H11 H 0.0463 0.7050 0.0534 0.072 Uiso 1 1 calc R . . C12 C 0.2099(3) 0.56461(14) 0.1874(4) 0.0417(7) Uani 1 1 d . . . C13 C 0.1402(4) 0.5470(2) 0.0599(5) 0.0502(11) Uani 1 1 d . . . H13 H 0.1142 0.5743 -0.0100 0.060 Uiso 1 1 calc R . . C14 C 0.1079(4) 0.4867(2) 0.0352(5) 0.0715(13) Uani 1 1 d . . . H14 H 0.0571 0.4758 -0.0470 0.086 Uiso 1 1 calc R . . C15 C 0.1538(4) 0.44515(19) 0.1363(5) 0.0701(12) Uani 1 1 d . . . H15 H 0.1369 0.4061 0.1187 0.084 Uiso 1 1 calc R . . C16 C 0.2250(4) 0.46177(16) 0.2636(5) 0.0583(11) Uani 1 1 d . . . H16 H 0.2545 0.4340 0.3310 0.070 Uiso 1 1 calc R . . C17 C 0.2522(3) 0.52160(14) 0.2896(3) 0.0435(9) Uani 1 1 d . . . C18 C 0.3197(3) 0.54188(19) 0.4188(5) 0.0457(10) Uani 1 1 d . . . C19 C 0.3787(4) 0.50758(19) 0.5289(5) 0.0637(11) Uani 1 1 d . . . H19 H 0.3734 0.4673 0.5232 0.076 Uiso 1 1 calc R . . C20 C 0.4480(4) 0.5347(2) 0.6516(5) 0.0672(12) Uani 1 1 d . . . H20 H 0.4894 0.5122 0.7245 0.081 Uiso 1 1 calc R . . C21 C 0.4517(3) 0.5935(2) 0.6590(4) 0.0598(10) Uani 1 1 d . . . H21 H 0.4943 0.6119 0.7384 0.072 Uiso 1 1 calc R . . C22 C 0.3921(3) 0.62603(18) 0.5483(4) 0.0505(8) Uani 1 1 d . . . H22 H 0.3959 0.6664 0.5551 0.061 Uiso 1 1 calc R . . C23 C 0.1757(3) 0.75775(16) 0.3557(4) 0.0563(10) Uani 1 1 d . . . H23A H 0.1893 0.7915 0.4160 0.068 Uiso 1 1 calc R . . H23B H 0.1250 0.7684 0.2676 0.068 Uiso 1 1 calc R . . C24 C 0.1343(3) 0.70762(18) 0.4203(4) 0.0570(10) Uani 1 1 d . . . H24A H 0.1845 0.6976 0.5093 0.068 Uiso 1 1 calc R . . H24B H 0.0692 0.7187 0.4338 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.04615(6) 0.03466(6) 0.03087(6) 0.00238(9) 0.01585(4) 0.00348(9) Cl1 0.0636(6) 0.0766(7) 0.0526(6) -0.0134(5) 0.0228(5) -0.0212(5) N1 0.0619(18) 0.0424(16) 0.0406(17) 0.0008(13) 0.0190(14) 0.0023(14) N3 0.0500(16) 0.0447(15) 0.0331(15) 0.0054(12) 0.0159(12) 0.0038(12) N2 0.049(2) 0.0430(18) 0.039(2) 0.0022(18) 0.0177(17) 0.0015(18) N4 0.0565(17) 0.0400(15) 0.0328(15) 0.0047(12) 0.0186(13) 0.0075(12) C1 0.051(2) 0.0325(18) 0.040(3) -0.0031(18) 0.019(2) -0.0032(18) C2 0.052(2) 0.042(2) 0.054(2) 0.0014(16) 0.0191(17) 0.0022(15) C3 0.049(2) 0.058(2) 0.068(3) -0.006(2) 0.0210(19) 0.0036(18) C4 0.060(3) 0.065(3) 0.072(3) -0.005(2) 0.036(2) -0.0024(19) C5 0.062(2) 0.057(2) 0.055(3) 0.0012(19) 0.031(2) -0.0055(19) C6 0.054(2) 0.0379(16) 0.041(2) -0.0030(15) 0.0238(16) -0.0080(15) C7 0.060(2) 0.0370(16) 0.0360(18) 0.0023(13) 0.0213(16) 0.0013(14) C8 0.084(3) 0.062(2) 0.048(2) 0.0084(18) 0.036(2) -0.002(2) C9 0.087(3) 0.078(3) 0.047(2) 0.023(2) 0.024(2) 0.023(3) C10 0.077(3) 0.100(4) 0.058(3) 0.034(3) 0.027(2) 0.035(3) C11 0.063(2) 0.075(3) 0.044(2) 0.0178(19) 0.0203(18) 0.026(2) C12 0.0507(18) 0.0378(17) 0.0430(19) -0.0072(15) 0.0240(15) -0.0038(14) C13 0.065(3) 0.048(2) 0.041(2) -0.0056(17) 0.021(2) 0.002(2) C14 0.083(3) 0.068(3) 0.067(3) -0.026(2) 0.030(3) -0.020(2) C15 0.102(3) 0.048(2) 0.072(3) -0.016(2) 0.045(3) -0.014(2) C16 0.079(3) 0.0384(17) 0.064(3) -0.0004(19) 0.032(2) 0.0005(17) C17 0.0531(18) 0.0339(16) 0.048(3) 0.0005(13) 0.022(2) 0.0021(15) C18 0.054(2) 0.0400(19) 0.048(3) 0.0001(17) 0.023(2) 0.0010(18) C19 0.084(3) 0.044(2) 0.066(3) 0.017(2) 0.028(2) 0.010(2) C20 0.079(3) 0.064(3) 0.051(3) 0.015(2) 0.011(2) 0.017(2) C21 0.065(3) 0.066(3) 0.040(2) 0.0006(18) 0.0061(18) 0.0034(19) C22 0.061(2) 0.0478(19) 0.039(2) 0.0005(17) 0.0126(17) 0.0005(17) C23 0.061(2) 0.048(2) 0.058(2) -0.0129(18) 0.0163(19) 0.0079(17) C24 0.056(2) 0.071(3) 0.046(2) -0.0085(19) 0.0208(18) 0.0112(19) _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 C12 2.021(3) . ? Ir1 C1 2.040(7) . ? Ir1 N4 2.069(3) . ? Ir1 N3 2.078(3) . ? Ir1 N2 2.195(5) . ? Ir1 N1 2.222(3) . ? N1 C23 1.525(5) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N3 C11 1.345(5) . ? N3 C7 1.398(4) . ? N2 C24 1.482(6) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N4 C22 1.351(5) . ? N4 C18 1.390(5) . ? C1 C2 1.385(8) . ? C1 C6 1.445(8) . ? C2 C3 1.378(5) . ? C2 H2 0.9300 . ? C3 C4 1.394(7) . ? C3 H3 0.9300 . ? C4 C5 1.401(7) . ? C4 H4 0.9300 . ? C5 C6 1.404(5) . ? C5 H5 0.9300 . ? C6 C7 1.446(5) . ? C7 C8 1.408(5) . ? C8 C9 1.353(6) . ? C8 H8 0.9300 . ? C9 C10 1.406(6) . ? C9 H9 0.9300 . ? C10 C11 1.378(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.397(6) . ? C12 C17 1.418(5) . ? C13 C14 1.450(6) . ? C13 H13 0.9300 . ? C14 C15 1.396(7) . ? C14 H14 0.9300 . ? C15 C16 1.397(7) . ? C15 H15 0.9300 . ? C16 C17 1.426(5) . ? C16 H16 0.9300 . ? C17 C18 1.418(6) . ? C18 C19 1.393(6) . ? C19 C20 1.441(7) . ? C19 H19 0.9300 . ? C20 C21 1.353(6) . ? C20 H20 0.9300 . ? C21 C22 1.377(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.524(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? 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 C12 Ir1 C1 90.32(15) . . ? C12 Ir1 N4 79.86(13) . . ? C1 Ir1 N4 90.9(2) . . ? C12 Ir1 N3 96.06(13) . . ? C1 Ir1 N3 80.9(2) . . ? N4 Ir1 N3 170.83(10) . . ? C12 Ir1 N2 92.41(13) . . ? C1 Ir1 N2 177.2(2) . . ? N4 Ir1 N2 89.03(17) . . ? N3 Ir1 N2 99.40(17) . . ? C12 Ir1 N1 171.05(12) . . ? C1 Ir1 N1 98.52(14) . . ? N4 Ir1 N1 98.45(11) . . ? N3 Ir1 N1 86.82(11) . . ? N2 Ir1 N1 78.74(13) . . ? C23 N1 Ir1 108.3(2) . . ? C23 N1 H1A 110.0 . . ? Ir1 N1 H1A 110.0 . . ? C23 N1 H1B 110.0 . . ? Ir1 N1 H1B 110.0 . . ? H1A N1 H1B 108.4 . . ? C11 N3 C7 119.0(3) . . ? C11 N3 Ir1 126.1(2) . . ? C7 N3 Ir1 114.9(2) . . ? C24 N2 Ir1 110.1(3) . . ? C24 N2 H2A 109.6 . . ? Ir1 N2 H2A 109.6 . . ? C24 N2 H2B 109.6 . . ? Ir1 N2 H2B 109.6 . . ? H2A N2 H2B 108.1 . . ? C22 N4 C18 119.5(3) . . ? C22 N4 Ir1 125.5(2) . . ? C18 N4 Ir1 114.7(3) . . ? C2 C1 C6 117.1(5) . . ? C2 C1 Ir1 129.7(5) . . ? C6 C1 Ir1 113.2(4) . . ? C3 C2 C1 121.1(4) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 122.6(4) . . ? C2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? C3 C4 C5 118.4(4) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C4 C5 C6 119.7(4) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 121.1(4) . . ? C5 C6 C7 122.4(3) . . ? C1 C6 C7 116.5(4) . . ? N3 C7 C8 118.9(3) . . ? N3 C7 C6 114.6(3) . . ? C8 C7 C6 126.6(3) . . ? C9 C8 C7 122.1(4) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 117.6(4) . . ? C8 C9 H9 121.2 . . ? C10 C9 H9 121.2 . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? N3 C11 C10 122.0(4) . . ? N3 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C13 C12 C17 118.3(3) . . ? C13 C12 Ir1 127.1(3) . . ? C17 C12 Ir1 114.4(3) . . ? C12 C13 C14 120.8(4) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 119.3(4) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 120.6(4) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C17 119.7(4) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C12 C17 C18 116.2(3) . . ? C12 C17 C16 121.1(4) . . ? C18 C17 C16 122.6(4) . . ? N4 C18 C19 119.0(4) . . ? N4 C18 C17 114.6(4) . . ? C19 C18 C17 126.3(4) . . ? C18 C19 C20 119.9(4) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C21 C20 C19 118.9(4) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C20 C21 C22 119.7(4) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? N4 C22 C21 123.1(4) . . ? N4 C22 H22 118.5 . . ? C21 C22 H22 118.5 . . ? C24 C23 N1 107.0(3) . . ? C24 C23 H23A 110.3 . . ? N1 C23 H23A 110.3 . . ? C24 C23 H23B 110.3 . . ? N1 C23 H23B 110.3 . . ? H23A C23 H23B 108.6 . . ? N2 C24 C23 107.6(3) . . ? N2 C24 H24A 110.2 . . ? C23 C24 H24A 110.2 . . ? N2 C24 H24B 110.2 . . ? C23 C24 H24B 110.2 . . ? H24A C24 H24B 108.5 . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.310 0.000 0.042 521 317 ' ' 2 0.810 0.500 0.042 521 317 ' ' _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.12 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.378 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.079 #===END data_(4a) _database_code_depnum_ccdc_archive 'CCDC 850268' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Ir N4, C24 H20 B' _chemical_formula_sum 'C48 H44 B Ir N4' _chemical_formula_weight 879.88 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' B B 0.0013 0.0007 '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' 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.212(5) _cell_length_b 26.279(11) _cell_length_c 14.334(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.113(11) _cell_angle_gamma 90.00 _cell_volume 3831(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7152 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 31.02 _exptl_crystal_description Needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1768 _exptl_absorpt_coefficient_mu 3.525 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8163 _exptl_absorpt_correction_T_max 0.9328 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23363 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.11 _reflns_number_total 4226 _reflns_number_gt 3885 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius X8 APEX' _computing_cell_refinement 'Bruker-Nonius X8 APEX' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0283P)^2^+4.2014P] 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 4226 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0624 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.5000 0.603054(5) 0.7500 0.03214(6) Uani 1 2 d S . . N1 N 0.6355(2) 0.66656(10) 0.77682(19) 0.0406(6) Uani 1 1 d . . . H1A H 0.6885 0.6608 0.8293 0.049 Uiso 1 1 calc R . . H1B H 0.6858 0.6702 0.7288 0.049 Uiso 1 1 calc R . . N3 N 0.4940(3) 0.59835(9) 0.89227(18) 0.0365(5) Uani 1 1 d . . . C1 C 0.6402(3) 0.55079(11) 0.7799(2) 0.0372(6) Uani 1 1 d . . . C2 C 0.7206(3) 0.52724(14) 0.7186(3) 0.0551(9) Uani 1 1 d . . . H2 H 0.7103 0.5352 0.6552 0.066 Uiso 1 1 calc R . . C3 C 0.8152(4) 0.49235(16) 0.7511(3) 0.0675(11) Uani 1 1 d . . . H3 H 0.8676 0.4772 0.7092 0.081 Uiso 1 1 calc R . . C4 C 0.8330(4) 0.47972(16) 0.8441(4) 0.0702(12) Uani 1 1 d . . . H4 H 0.8953 0.4555 0.8646 0.084 Uiso 1 1 calc R . . C5 C 0.7584(3) 0.50302(14) 0.9070(3) 0.0588(9) Uani 1 1 d . . . H5 H 0.7717 0.4952 0.9704 0.071 Uiso 1 1 calc R . . C6 C 0.6629(3) 0.53829(11) 0.8754(2) 0.0414(7) Uani 1 1 d . . . C7 C 0.5801(3) 0.56520(12) 0.9367(2) 0.0410(7) Uani 1 1 d . . . C8 C 0.5829(4) 0.55905(15) 1.0333(2) 0.0578(9) Uani 1 1 d . . . H8 H 0.6427 0.5365 1.0636 0.069 Uiso 1 1 calc R . . C9 C 0.4991(5) 0.58563(17) 1.0844(3) 0.0661(11) Uani 1 1 d . . . H9 H 0.5013 0.5812 1.1489 0.079 Uiso 1 1 calc R . . C10 C 0.4117(5) 0.61898(17) 1.0390(3) 0.0643(10) Uani 1 1 d . . . H10 H 0.3535 0.6375 1.0721 0.077 Uiso 1 1 calc R . . C11 C 0.4122(4) 0.62433(15) 0.9438(2) 0.0522(8) Uani 1 1 d . . . H11 H 0.3531 0.6470 0.9132 0.063 Uiso 1 1 calc R . . C12 C 0.5567(3) 0.71331(12) 0.7876(2) 0.0448(7) Uani 1 1 d . . . H12A H 0.6108 0.7432 0.7815 0.054 Uiso 1 1 calc R . . H12B H 0.5237 0.7139 0.8490 0.054 Uiso 1 1 calc R . . B1 B 1.0000 0.72817(17) 0.7500 0.0313(9) Uani 1 2 d S . . C1' C 0.9690(3) 0.69186(12) 0.8405(2) 0.0390(6) Uani 1 1 d . . . C2' C 1.0274(3) 0.64434(14) 0.8573(3) 0.0529(8) Uani 1 1 d . . . H2A H 1.0876 0.6330 0.8169 0.063 Uiso 1 1 calc R . . C3' C 0.9999(5) 0.61330(16) 0.9312(3) 0.0677(11) Uani 1 1 d . . . H3A H 1.0407 0.5818 0.9391 0.081 Uiso 1 1 calc R . . C4' C 0.9124(4) 0.62897(17) 0.9930(3) 0.0640(11) Uani 1 1 d . . . H4A H 0.8910 0.6077 1.0412 0.077 Uiso 1 1 calc R . . C5' C 0.8578(4) 0.67592(17) 0.9824(2) 0.0589(10) Uani 1 1 d . . . H5A H 0.8017 0.6876 1.0254 0.071 Uiso 1 1 calc R . . C6' C 0.8854(3) 0.70668(14) 0.9076(2) 0.0480(8) Uani 1 1 d . . . H6A H 0.8463 0.7386 0.9019 0.058 Uiso 1 1 calc R . . C7' C 0.8735(3) 0.76490(11) 0.7193(2) 0.0354(6) Uani 1 1 d . . . C8' C 0.8461(3) 0.80746(12) 0.7723(2) 0.0422(7) Uani 1 1 d . . . H8A H 0.9028 0.8152 0.8248 0.051 Uiso 1 1 calc R . . C9' C 0.7384(3) 0.83886(13) 0.7507(2) 0.0495(8) Uani 1 1 d . . . H9A H 0.7237 0.8666 0.7887 0.059 Uiso 1 1 calc R . . C10' C 0.6534(3) 0.82890(14) 0.6729(3) 0.0515(8) Uani 1 1 d . . . H10A H 0.5806 0.8496 0.6581 0.062 Uiso 1 1 calc R . . C11' C 0.6774(3) 0.78807(14) 0.6173(2) 0.0475(8) Uani 1 1 d . . . H11A H 0.6211 0.7813 0.5641 0.057 Uiso 1 1 calc R . . C12' C 0.7850(3) 0.75666(12) 0.6398(2) 0.0391(6) Uani 1 1 d . . . H12C H 0.7991 0.7292 0.6009 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02914(9) 0.03177(9) 0.03443(9) 0.000 -0.00324(6) 0.000 N1 0.0328(12) 0.0412(14) 0.0468(14) -0.0056(11) -0.0014(11) -0.0030(10) N3 0.0360(13) 0.0376(13) 0.0351(13) -0.0005(10) -0.0016(10) 0.0005(10) C1 0.0309(13) 0.0341(14) 0.0453(16) -0.0063(12) -0.0040(12) 0.0000(11) C2 0.0479(19) 0.057(2) 0.059(2) -0.0153(17) -0.0005(16) 0.0107(16) C3 0.054(2) 0.061(2) 0.086(3) -0.021(2) 0.001(2) 0.0172(19) C4 0.056(2) 0.052(2) 0.099(3) 0.004(2) -0.013(2) 0.0207(18) C5 0.049(2) 0.053(2) 0.072(2) 0.0134(18) -0.0077(18) 0.0107(16) C6 0.0361(15) 0.0349(15) 0.0510(18) 0.0045(13) -0.0086(13) -0.0011(12) C7 0.0414(16) 0.0377(15) 0.0423(16) 0.0037(13) -0.0052(13) -0.0047(13) C8 0.066(2) 0.059(2) 0.0452(19) 0.0134(16) -0.0107(17) 0.0006(18) C9 0.086(3) 0.075(3) 0.0373(19) 0.0013(18) 0.005(2) -0.012(2) C10 0.077(3) 0.068(2) 0.050(2) -0.0080(19) 0.017(2) 0.002(2) C11 0.058(2) 0.052(2) 0.0478(19) -0.0024(16) 0.0087(16) 0.0103(17) C12 0.0454(17) 0.0362(15) 0.0529(19) -0.0045(14) 0.0048(14) -0.0033(13) B1 0.0252(19) 0.035(2) 0.033(2) 0.000 -0.0002(16) 0.000 C1' 0.0317(13) 0.0434(16) 0.0395(15) 0.0018(13) -0.0094(12) -0.0067(12) C2' 0.0508(19) 0.0491(19) 0.058(2) 0.0115(16) 0.0021(16) -0.0004(16) C3' 0.078(3) 0.053(2) 0.071(3) 0.0186(19) -0.002(2) -0.007(2) C4' 0.066(2) 0.073(3) 0.051(2) 0.017(2) -0.0095(19) -0.027(2) C5' 0.052(2) 0.088(3) 0.0358(17) 0.0014(18) -0.0034(15) -0.0112(19) C6' 0.0448(17) 0.059(2) 0.0384(16) 0.0006(14) -0.0070(14) -0.0012(15) C7' 0.0289(13) 0.0406(15) 0.0357(14) 0.0021(12) -0.0018(11) -0.0047(11) C8' 0.0403(15) 0.0415(16) 0.0436(16) -0.0020(13) -0.0037(13) 0.0017(13) C9' 0.0501(19) 0.0437(17) 0.055(2) 0.0028(15) 0.0046(16) 0.0089(14) C10' 0.0412(17) 0.058(2) 0.055(2) 0.0190(17) 0.0025(15) 0.0140(15) C11' 0.0363(16) 0.065(2) 0.0398(16) 0.0121(15) -0.0056(13) 0.0020(15) C12' 0.0338(14) 0.0480(17) 0.0346(15) 0.0019(13) -0.0020(12) -0.0027(13) _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 C1 2.003(3) 2_656 ? Ir1 C1 2.003(3) . ? Ir1 N3 2.050(3) . ? Ir1 N3 2.050(3) 2_656 ? Ir1 N1 2.180(3) . ? Ir1 N1 2.180(3) 2_656 ? N1 C12 1.484(4) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N3 C11 1.349(4) . ? N3 C7 1.356(4) . ? C1 C2 1.399(4) . ? C1 C6 1.406(4) . ? C2 C3 1.382(5) . ? C2 H2 0.9300 . ? C3 C4 1.370(6) . ? C3 H3 0.9300 . ? C4 C5 1.375(6) . ? C4 H4 0.9300 . ? C5 C6 1.392(4) . ? C5 H5 0.9300 . ? C6 C7 1.457(5) . ? C7 C8 1.392(5) . ? C8 C9 1.367(6) . ? C8 H8 0.9300 . ? C9 C10 1.373(6) . ? C9 H9 0.9300 . ? C10 C11 1.373(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C12 1.510(6) 2_656 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? B1 C7' 1.641(4) . ? B1 C7' 1.641(4) 2_756 ? B1 C1' 1.664(4) 2_756 ? B1 C1' 1.664(4) . ? C1' C2' 1.396(5) . ? C1' C6' 1.397(5) . ? C2' C3' 1.386(5) . ? C2' H2A 0.9300 . ? C3' C4' 1.375(6) . ? C3' H3A 0.9300 . ? C4' C5' 1.357(6) . ? C4' H4A 0.9300 . ? C5' C6' 1.392(5) . ? C5' H5A 0.9300 . ? C6' H6A 0.9300 . ? C7' C8' 1.395(4) . ? C7' C12' 1.407(4) . ? C8' C9' 1.387(4) . ? C8' H8A 0.9300 . ? C9' C10' 1.376(5) . ? C9' H9A 0.9300 . ? C10' C11' 1.371(5) . ? C10' H10A 0.9300 . ? C11' C12' 1.390(4) . ? C11' H11A 0.9300 . ? C12' H12C 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 C1 93.38(17) 2_656 . ? C1 Ir1 N3 95.01(11) 2_656 . ? C1 Ir1 N3 80.21(11) . . ? C1 Ir1 N3 80.21(11) 2_656 2_656 ? C1 Ir1 N3 95.01(11) . 2_656 ? N3 Ir1 N3 173.08(13) . 2_656 ? C1 Ir1 N1 173.30(10) 2_656 . ? C1 Ir1 N1 93.27(12) . . ? N3 Ir1 N1 86.88(10) . . ? N3 Ir1 N1 98.44(10) 2_656 . ? C1 Ir1 N1 93.27(12) 2_656 2_656 ? C1 Ir1 N1 173.30(10) . 2_656 ? N3 Ir1 N1 98.44(10) . 2_656 ? N3 Ir1 N1 86.88(10) 2_656 2_656 ? N1 Ir1 N1 80.09(14) . 2_656 ? C12 N1 Ir1 108.08(18) . . ? C12 N1 H1A 110.1 . . ? Ir1 N1 H1A 110.1 . . ? C12 N1 H1B 110.1 . . ? Ir1 N1 H1B 110.1 . . ? H1A N1 H1B 108.4 . . ? C11 N3 C7 118.4(3) . . ? C11 N3 Ir1 126.1(2) . . ? C7 N3 Ir1 115.5(2) . . ? C2 C1 C6 116.9(3) . . ? C2 C1 Ir1 128.1(3) . . ? C6 C1 Ir1 114.9(2) . . ? C3 C2 C1 120.9(4) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 121.5(3) . . ? C5 C6 C7 123.6(3) . . ? C1 C6 C7 114.9(3) . . ? N3 C7 C8 119.8(3) . . ? N3 C7 C6 114.5(3) . . ? C8 C7 C6 125.7(3) . . ? C9 C8 C7 121.0(3) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 119.0(4) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 C11 118.5(4) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? N3 C11 C10 123.3(4) . . ? N3 C11 H11 118.3 . . ? C10 C11 H11 118.3 . . ? N1 C12 C12 108.3(2) . 2_656 ? N1 C12 H12A 110.0 . . ? C12 C12 H12A 110.0 2_656 . ? N1 C12 H12B 110.0 . . ? C12 C12 H12B 110.0 2_656 . ? H12A C12 H12B 108.4 . . ? C7' B1 C7' 107.9(3) . 2_756 ? C7' B1 C1' 109.16(14) . 2_756 ? C7' B1 C1' 110.28(14) 2_756 2_756 ? C7' B1 C1' 110.28(14) . . ? C7' B1 C1' 109.16(14) 2_756 . ? C1' B1 C1' 110.0(3) 2_756 . ? C2' C1' C6' 114.2(3) . . ? C2' C1' B1 122.6(3) . . ? C6' C1' B1 123.2(3) . . ? C3' C2' C1' 123.0(4) . . ? C3' C2' H2A 118.5 . . ? C1' C2' H2A 118.5 . . ? C4' C3' C2' 120.2(4) . . ? C4' C3' H3A 119.9 . . ? C2' C3' H3A 119.9 . . ? C5' C4' C3' 119.0(4) . . ? C5' C4' H4A 120.5 . . ? C3' C4' H4A 120.5 . . ? C4' C5' C6' 120.3(4) . . ? C4' C5' H5A 119.9 . . ? C6' C5' H5A 119.9 . . ? C5' C6' C1' 123.1(4) . . ? C5' C6' H6A 118.4 . . ? C1' C6' H6A 118.4 . . ? C8' C7' C12' 114.8(3) . . ? C8' C7' B1 121.2(2) . . ? C12' C7' B1 124.1(3) . . ? C9' C8' C7' 123.3(3) . . ? C9' C8' H8A 118.4 . . ? C7' C8' H8A 118.4 . . ? C10' C9' C8' 119.9(3) . . ? C10' C9' H9A 120.1 . . ? C8' C9' H9A 120.1 . . ? C11' C10' C9' 119.2(3) . . ? C11' C10' H10A 120.4 . . ? C9' C10' H10A 120.4 . . ? C10' C11' C12' 120.6(3) . . ? C10' C11' H11A 119.7 . . ? C12' C11' H11A 119.7 . . ? C11' C12' C7' 122.3(3) . . ? C11' C12' H12C 118.9 . . ? C7' C12' H12C 118.9 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.11 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.036 _refine_diff_density_min -1.011 _refine_diff_density_rms 0.082 #===END