# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Connelly, Neil' _publ_contact_author_name 'Connelly, Neil' _publ_contact_author_email neil.connelly@bristol.ac.uk _publ_section_title ; Potassium S2N-heteroscorpionates: structure and iridaboratrane formation ; # Attachment '- all.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 803997' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 B K N6 O S2' _chemical_formula_sum 'C14 H22 B K N6 O S2' _chemical_formula_weight 404.41 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.9487(14) _cell_length_b 37.295(8) _cell_length_c 14.782(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.10(3) _cell_angle_gamma 90.00 _cell_volume 3820.9(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.512 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.87700 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 43923 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -48 _diffrn_reflns_limit_k_max 48 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8744 _reflns_number_gt 7979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 '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^)+(0.0335P)^2^+4.3745P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8744 _refine_ls_number_parameters 467 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.195 _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 B2 B 1.1585(4) 0.09529(7) 0.86923(16) 0.0101(5) Uani 1 1 d . . . H2B H 1.0560 0.0971 0.8184 0.012 Uiso 1 1 calc R . . B1 B 0.5825(4) 0.15552(7) 0.47758(16) 0.0105(5) Uani 1 1 d . . . H1B H 0.4912 0.1543 0.5268 0.013 Uiso 1 1 calc R . . C1 C 0.6776(3) 0.08902(6) 0.50807(15) 0.0109(4) Uani 1 1 d . . . C2 C 0.6787(3) 0.10583(6) 0.36376(15) 0.0127(4) Uani 1 1 d . . . H2 H 0.6670 0.1203 0.3108 0.015 Uiso 1 1 calc R . . C3 C 0.7277(3) 0.07097(6) 0.36699(15) 0.0130(4) Uani 1 1 d . . . H3 H 0.7567 0.0563 0.3173 0.016 Uiso 1 1 calc R . . C4 C 0.7671(4) 0.02488(6) 0.49197(16) 0.0178(5) Uani 1 1 d . . . H4A H 0.8751 0.0258 0.5383 0.027 Uiso 1 1 calc R . . H4B H 0.8006 0.0091 0.4424 0.027 Uiso 1 1 calc R . . H4C H 0.6524 0.0155 0.5189 0.027 Uiso 1 1 calc R . . C5 C 0.7683(3) 0.20880(6) 0.55585(14) 0.0112(4) Uani 1 1 d . . . C6 C 0.9517(3) 0.16917(6) 0.48902(15) 0.0134(4) Uani 1 1 d . . . H6 H 0.9896 0.1487 0.4564 0.016 Uiso 1 1 calc R . . C7 C 1.0702(3) 0.19505(6) 0.52336(15) 0.0144(5) Uani 1 1 d . . . H7 H 1.2060 0.1963 0.5199 0.017 Uiso 1 1 calc R . . C8 C 1.0290(4) 0.25045(6) 0.61627(16) 0.0171(5) Uani 1 1 d . . . H8A H 0.9226 0.2670 0.6256 0.026 Uiso 1 1 calc R . . H8B H 1.1265 0.2627 0.5828 0.026 Uiso 1 1 calc R . . H8C H 1.0872 0.2425 0.6752 0.026 Uiso 1 1 calc R . . C9 C 0.5332(3) 0.19447(6) 0.32505(15) 0.0129(4) Uani 1 1 d . . . C10 C 0.3945(4) 0.19218(6) 0.25320(15) 0.0160(5) Uani 1 1 d . . . H10 H 0.3906 0.2054 0.1981 0.019 Uiso 1 1 calc R . . C11 C 0.2614(3) 0.16650(6) 0.27812(15) 0.0148(5) Uani 1 1 d . . . C12 C 0.7073(4) 0.21817(7) 0.33301(16) 0.0178(5) Uani 1 1 d . . . H12A H 0.7008 0.2339 0.3858 0.027 Uiso 1 1 calc R . . H12B H 0.7112 0.2328 0.2780 0.027 Uiso 1 1 calc R . . H12C H 0.8239 0.2034 0.3404 0.027 Uiso 1 1 calc R . . C13 C 0.0832(4) 0.15271(7) 0.22641(16) 0.0209(5) Uani 1 1 d . . . H13A H 0.1192 0.1402 0.1718 0.031 Uiso 1 1 calc R . . H13B H -0.0022 0.1728 0.2090 0.031 Uiso 1 1 calc R . . H13C H 0.0162 0.1360 0.2646 0.031 Uiso 1 1 calc R . . C14 C 1.2305(3) 0.16313(6) 0.84782(15) 0.0116(4) Uani 1 1 d . . . C15 C 1.2917(3) 0.14271(6) 0.98778(14) 0.0133(4) Uani 1 1 d . . . H15 H 1.3033 0.1269 1.0382 0.016 Uiso 1 1 calc R . . C16 C 1.3340(3) 0.17785(6) 0.98995(15) 0.0152(5) Uani 1 1 d . . . H16 H 1.3813 0.1913 1.0414 0.018 Uiso 1 1 calc R . . C17 C 1.3075(4) 0.22788(6) 0.87408(17) 0.0207(5) Uani 1 1 d . . . H17A H 1.3766 0.2293 0.8187 0.031 Uiso 1 1 calc R . . H17B H 1.3770 0.2418 0.9222 0.031 Uiso 1 1 calc R . . H17C H 1.1772 0.2377 0.8623 0.031 Uiso 1 1 calc R . . C18 C 1.3310(3) 0.04311(6) 0.78974(14) 0.0104(4) Uani 1 1 d . . . C19 C 1.5253(3) 0.08175(6) 0.86627(15) 0.0130(4) Uani 1 1 d . . . H19 H 1.5687 0.1019 0.9015 0.016 Uiso 1 1 calc R . . C20 C 1.6385(3) 0.05598(6) 0.83437(15) 0.0140(4) Uani 1 1 d . . . H20 H 1.7752 0.0545 0.8425 0.017 Uiso 1 1 calc R . . C21 C 1.5799(3) 0.00066(6) 0.73967(16) 0.0167(5) Uani 1 1 d . . . H21A H 1.5395 -0.0210 0.7706 0.025 Uiso 1 1 calc R . . H21B H 1.7208 0.0009 0.7389 0.025 Uiso 1 1 calc R . . H21C H 1.5218 0.0009 0.6773 0.025 Uiso 1 1 calc R . . C22 C 1.1284(3) 0.05094(6) 1.01189(15) 0.0139(4) Uani 1 1 d . . . C23 C 1.0048(4) 0.05171(7) 1.08066(16) 0.0176(5) Uani 1 1 d . . . H23 H 1.0049 0.0359 1.1311 0.021 Uiso 1 1 calc R . . C24 C 0.8798(3) 0.08028(6) 1.06120(15) 0.0143(5) Uani 1 1 d . . . C25 C 1.2870(4) 0.02475(7) 0.99898(16) 0.0187(5) Uani 1 1 d . . . H25A H 1.2588 0.0116 0.9422 0.028 Uiso 1 1 calc R . . H25B H 1.2967 0.0079 1.0499 0.028 Uiso 1 1 calc R . . H25C H 1.4093 0.0377 0.9963 0.028 Uiso 1 1 calc R . . C26 C 0.7148(4) 0.09331(7) 1.11235(16) 0.0207(5) Uani 1 1 d . . . H26A H 0.6827 0.1180 1.0942 0.031 Uiso 1 1 calc R . . H26B H 0.7514 0.0926 1.1776 0.031 Uiso 1 1 calc R . . H26C H 0.6024 0.0779 1.0988 0.031 Uiso 1 1 calc R . . C27 C 0.8142(4) 0.18612(7) 0.9592(2) 0.0263(6) Uani 1 1 d . . . H27A H 0.9236 0.1984 0.9345 0.039 Uiso 1 1 calc R . . H27B H 0.8527 0.1772 1.0201 0.039 Uiso 1 1 calc R . . H27C H 0.7064 0.2029 0.9623 0.039 Uiso 1 1 calc R . . C28 C 1.2130(4) 0.06389(7) 0.39033(19) 0.0226(5) Uani 1 1 d . . . H28A H 1.3491 0.0570 0.3996 0.034 Uiso 1 1 calc R . . H28B H 1.1834 0.0704 0.3266 0.034 Uiso 1 1 calc R . . H28C H 1.1316 0.0437 0.4060 0.034 Uiso 1 1 calc R . . K2 K 1.15367(8) 0.094908(14) 0.62676(3) 0.01681(12) Uani 1 1 d . . . K1 K 0.65926(8) 0.161114(14) 0.72550(3) 0.01731(12) Uani 1 1 d . . . N1 N 0.6480(3) 0.11710(5) 0.45125(12) 0.0109(4) Uani 1 1 d . . . N2 N 0.7275(3) 0.06069(5) 0.45678(12) 0.0118(4) Uani 1 1 d . . . N3 N 0.7643(3) 0.17737(5) 0.50915(12) 0.0102(4) Uani 1 1 d . . . N4 N 0.9557(3) 0.21952(5) 0.56458(12) 0.0124(4) Uani 1 1 d . . . N5 N 0.4804(3) 0.17133(5) 0.38966(12) 0.0103(4) Uani 1 1 d . . . N6 N 0.3128(3) 0.15394(5) 0.36043(12) 0.0125(4) Uani 1 1 d . . . N7 N 1.2284(3) 0.13334(5) 0.89978(12) 0.0102(4) Uani 1 1 d . . . N8 N 1.2950(3) 0.19065(5) 0.90234(13) 0.0137(4) Uani 1 1 d . . . N9 N 1.3336(3) 0.07387(5) 0.83884(12) 0.0109(4) Uani 1 1 d . . . N10 N 1.5168(3) 0.03211(5) 0.78752(12) 0.0118(4) Uani 1 1 d . . . N11 N 1.0761(3) 0.07817(5) 0.95374(12) 0.0112(4) Uani 1 1 d . . . N12 N 0.9221(3) 0.09659(5) 0.98495(12) 0.0127(4) Uani 1 1 d . . . O2 O 1.1765(3) 0.09357(5) 0.44636(11) 0.0166(3) Uani 1 1 d . . . H2O H 1.225(4) 0.1108(9) 0.423(2) 0.025 Uiso 1 1 d . . . O1 O 0.7565(3) 0.15703(5) 0.90223(11) 0.0168(3) Uani 1 1 d . . . H1O H 0.809(4) 0.1387(9) 0.923(2) 0.025 Uiso 1 1 d . . . S1 S 0.66233(9) 0.086858(15) 0.62247(4) 0.01410(12) Uani 1 1 d . . . S2 S 0.57817(8) 0.230648(15) 0.59738(4) 0.01352(12) Uani 1 1 d . . . S3 S 1.17061(9) 0.167793(15) 0.73418(4) 0.01416(12) Uani 1 1 d . . . S4 S 1.13509(8) 0.021378(15) 0.73927(4) 0.01331(12) 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 B2 0.0108(12) 0.0109(11) 0.0084(10) 0.0019(9) -0.0015(9) 0.0011(9) B1 0.0117(12) 0.0099(11) 0.0098(11) -0.0003(9) 0.0003(9) 0.0015(9) C1 0.0072(10) 0.0119(11) 0.0136(10) -0.0004(8) 0.0007(8) -0.0009(8) C2 0.0129(11) 0.0153(11) 0.0099(10) -0.0009(8) 0.0014(8) -0.0007(9) C3 0.0140(11) 0.0142(11) 0.0109(10) -0.0028(8) 0.0010(8) -0.0008(9) C4 0.0228(13) 0.0107(11) 0.0198(12) 0.0002(9) 0.0008(9) 0.0029(9) C5 0.0122(11) 0.0109(11) 0.0106(10) 0.0018(8) 0.0016(8) 0.0005(8) C6 0.0127(11) 0.0150(11) 0.0128(10) -0.0004(8) 0.0024(8) 0.0042(9) C7 0.0125(11) 0.0166(12) 0.0139(11) 0.0019(9) 0.0000(8) 0.0021(9) C8 0.0173(12) 0.0129(11) 0.0206(12) -0.0028(9) -0.0025(9) -0.0038(9) C9 0.0163(11) 0.0086(10) 0.0139(10) 0.0006(8) 0.0025(8) 0.0020(9) C10 0.0206(12) 0.0141(11) 0.0131(11) 0.0015(9) -0.0010(9) 0.0030(9) C11 0.0151(11) 0.0156(11) 0.0135(10) -0.0009(9) -0.0002(8) 0.0031(9) C12 0.0200(12) 0.0171(12) 0.0161(11) 0.0047(9) 0.0007(9) -0.0034(10) C13 0.0206(13) 0.0270(14) 0.0144(11) -0.0011(10) -0.0029(9) -0.0032(10) C14 0.0100(10) 0.0111(11) 0.0141(10) -0.0015(8) 0.0030(8) 0.0000(8) C15 0.0133(11) 0.0178(12) 0.0088(10) -0.0004(8) 0.0002(8) 0.0004(9) C16 0.0135(11) 0.0180(12) 0.0142(11) -0.0035(9) 0.0018(8) 0.0008(9) C17 0.0259(14) 0.0107(11) 0.0253(13) -0.0001(10) 0.0019(10) -0.0030(10) C18 0.0123(11) 0.0099(10) 0.0092(10) 0.0018(8) 0.0009(8) -0.0001(8) C19 0.0125(11) 0.0135(11) 0.0128(10) 0.0004(8) -0.0016(8) -0.0021(9) C20 0.0115(11) 0.0154(11) 0.0149(11) 0.0012(9) 0.0003(8) -0.0014(9) C21 0.0162(12) 0.0144(11) 0.0198(12) -0.0040(9) 0.0028(9) 0.0020(9) C22 0.0169(12) 0.0109(11) 0.0136(10) 0.0026(8) -0.0017(9) -0.0017(9) C23 0.0207(13) 0.0190(12) 0.0130(11) 0.0049(9) 0.0012(9) -0.0009(10) C24 0.0143(11) 0.0170(12) 0.0115(10) -0.0007(9) 0.0004(8) -0.0054(9) C25 0.0228(13) 0.0147(12) 0.0190(12) 0.0057(9) 0.0034(10) 0.0055(10) C26 0.0180(12) 0.0295(14) 0.0150(11) -0.0013(10) 0.0043(9) -0.0010(10) C27 0.0208(13) 0.0181(13) 0.0390(16) -0.0053(11) -0.0047(11) 0.0011(11) C28 0.0211(13) 0.0150(12) 0.0327(14) -0.0030(10) 0.0083(11) 0.0001(10) K2 0.0214(3) 0.0151(2) 0.0138(2) -0.00072(19) 0.00077(19) 0.0002(2) K1 0.0213(3) 0.0164(3) 0.0142(2) -0.00006(19) 0.00141(19) 0.0000(2) N1 0.0123(9) 0.0108(9) 0.0096(9) -0.0003(7) 0.0005(7) 0.0015(7) N2 0.0117(9) 0.0105(9) 0.0130(9) -0.0005(7) -0.0001(7) 0.0001(7) N3 0.0108(9) 0.0096(9) 0.0103(8) -0.0006(7) 0.0006(7) 0.0014(7) N4 0.0120(9) 0.0120(9) 0.0128(9) 0.0008(7) -0.0007(7) 0.0004(7) N5 0.0098(9) 0.0097(9) 0.0113(9) -0.0010(7) -0.0001(7) 0.0006(7) N6 0.0120(9) 0.0125(9) 0.0128(9) -0.0015(7) 0.0004(7) 0.0002(7) N7 0.0105(9) 0.0106(9) 0.0096(8) -0.0010(7) 0.0016(7) 0.0007(7) N8 0.0135(10) 0.0119(9) 0.0156(9) -0.0024(7) 0.0013(7) -0.0017(7) N9 0.0120(9) 0.0099(9) 0.0106(9) 0.0001(7) -0.0005(7) -0.0010(7) N10 0.0107(9) 0.0123(9) 0.0125(9) -0.0003(7) 0.0013(7) 0.0012(7) N11 0.0110(9) 0.0110(9) 0.0116(9) -0.0002(7) 0.0007(7) 0.0000(7) N12 0.0118(9) 0.0142(10) 0.0123(9) -0.0016(7) 0.0016(7) 0.0011(7) O2 0.0189(9) 0.0141(8) 0.0174(8) -0.0004(7) 0.0054(7) -0.0020(7) O1 0.0187(9) 0.0141(8) 0.0172(8) -0.0006(7) -0.0019(7) 0.0026(7) S1 0.0191(3) 0.0135(3) 0.0097(2) 0.0015(2) 0.0007(2) 0.0022(2) S2 0.0143(3) 0.0116(3) 0.0147(3) -0.0033(2) 0.0016(2) 0.0026(2) S3 0.0194(3) 0.0124(3) 0.0105(2) 0.0020(2) 0.0006(2) -0.0007(2) S4 0.0123(3) 0.0128(3) 0.0146(3) -0.0025(2) -0.0005(2) -0.0020(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B2 N9 1.549(3) . ? B2 N11 1.549(3) . ? B2 N7 1.556(3) . ? B2 H2B 1.0000 . ? B1 N3 1.547(3) . ? B1 N5 1.552(3) . ? B1 N1 1.561(3) . ? B1 H1B 1.0000 . ? C1 N1 1.349(3) . ? C1 N2 1.360(3) . ? C1 S1 1.704(2) . ? C2 C3 1.344(3) . ? C2 N1 1.391(3) . ? C2 H2 0.9500 . ? C3 N2 1.382(3) . ? C3 H3 0.9500 . ? C4 N2 1.452(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N4 1.359(3) . ? C5 N3 1.360(3) . ? C5 S2 1.704(2) . ? C6 C7 1.344(3) . ? C6 N3 1.390(3) . ? C6 H6 0.9500 . ? C7 N4 1.381(3) . ? C7 H7 0.9500 . ? C8 N4 1.455(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 N5 1.357(3) . ? C9 C10 1.385(3) . ? C9 C12 1.496(3) . ? C10 C11 1.399(3) . ? C10 H10 0.9500 . ? C11 N6 1.328(3) . ? C11 C13 1.499(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N7 1.352(3) . ? C14 N8 1.361(3) . ? C14 S3 1.710(2) . ? C15 C16 1.343(3) . ? C15 N7 1.388(3) . ? C15 H15 0.9500 . ? C16 N8 1.389(3) . ? C16 H16 0.9500 . ? C17 N8 1.454(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 N9 1.357(3) . ? C18 N10 1.358(3) . ? C18 S4 1.709(2) . ? C19 C20 1.348(3) . ? C19 N9 1.396(3) . ? C19 H19 0.9500 . ? C20 N10 1.380(3) . ? C20 H20 0.9500 . ? C21 N10 1.453(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 N11 1.363(3) . ? C22 C23 1.377(3) . ? C22 C25 1.494(3) . ? C23 C24 1.392(3) . ? C23 H23 0.9500 . ? C24 N12 1.332(3) . ? C24 C26 1.499(3) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 O1 1.414(3) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 O2 1.416(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? K2 O2 2.6831(18) . ? K2 S3 3.1460(9) . ? K2 S4 3.2146(9) . ? K2 S1 3.4234(11) . ? K2 S1 3.5523(11) 1_655 ? K2 K1 4.4539(11) 1_655 ? K2 H1B 5.2255 . ? K1 O1 2.6556(18) . ? K1 S1 3.1612(9) . ? K1 S2 3.2367(9) . ? K1 S3 3.4162(11) 1_455 ? K1 S3 3.5551(11) . ? K1 H2B 3.8273 . ? K1 K2 4.4538(11) 1_455 ? N5 N6 1.375(3) . ? N11 N12 1.378(3) . ? O2 H2O 0.81(3) . ? O1 H1O 0.82(3) . ? S1 K2 3.5523(11) 1_455 ? S3 K1 3.4162(11) 1_655 ? 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 N9 B2 N11 111.38(18) . . ? N9 B2 N7 108.62(18) . . ? N11 B2 N7 105.53(17) . . ? N9 B2 H2B 110.4 . . ? N11 B2 H2B 110.4 . . ? N7 B2 H2B 110.4 . . ? N3 B1 N5 111.54(18) . . ? N3 B1 N1 108.19(18) . . ? N5 B1 N1 105.31(17) . . ? N3 B1 H1B 110.6 . . ? N5 B1 H1B 110.6 . . ? N1 B1 H1B 110.6 . . ? N1 C1 N2 106.84(18) . . ? N1 C1 S1 129.58(17) . . ? N2 C1 S1 123.58(17) . . ? C3 C2 N1 108.33(19) . . ? C3 C2 H2 125.8 . . ? N1 C2 H2 125.8 . . ? C2 C3 N2 106.55(19) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N4 C5 N3 106.65(19) . . ? N4 C5 S2 125.98(17) . . ? N3 C5 S2 127.36(17) . . ? C7 C6 N3 108.6(2) . . ? C7 C6 H6 125.7 . . ? N3 C6 H6 125.7 . . ? C6 C7 N4 106.5(2) . . ? C6 C7 H7 126.7 . . ? N4 C7 H7 126.7 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 C10 107.0(2) . . ? N5 C9 C12 125.3(2) . . ? C10 C9 C12 127.7(2) . . ? C9 C10 C11 106.1(2) . . ? C9 C10 H10 127.0 . . ? C11 C10 H10 127.0 . . ? N6 C11 C10 110.1(2) . . ? N6 C11 C13 120.3(2) . . ? C10 C11 C13 129.7(2) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N7 C14 N8 107.46(19) . . ? N7 C14 S3 129.04(17) . . ? N8 C14 S3 123.48(17) . . ? C16 C15 N7 108.8(2) . . ? C16 C15 H15 125.6 . . ? N7 C15 H15 125.6 . . ? C15 C16 N8 106.6(2) . . ? C15 C16 H16 126.7 . . ? N8 C16 H16 126.7 . . ? N8 C17 H17A 109.5 . . ? N8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N9 C18 N10 106.97(19) . . ? N9 C18 S4 127.89(17) . . ? N10 C18 S4 125.14(17) . . ? C20 C19 N9 108.5(2) . . ? C20 C19 H19 125.8 . . ? N9 C19 H19 125.8 . . ? C19 C20 N10 106.5(2) . . ? C19 C20 H20 126.8 . . ? N10 C20 H20 126.8 . . ? N10 C21 H21A 109.5 . . ? N10 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N10 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N11 C22 C23 107.3(2) . . ? N11 C22 C25 124.9(2) . . ? C23 C22 C25 127.8(2) . . ? C22 C23 C24 106.0(2) . . ? C22 C23 H23 127.0 . . ? C24 C23 H23 127.0 . . ? N12 C24 C23 110.6(2) . . ? N12 C24 C26 120.1(2) . . ? C23 C24 C26 129.2(2) . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O1 C27 H27A 109.5 . . ? O1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O2 C28 H28A 109.5 . . ? O2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O2 K2 S3 120.99(4) . . ? O2 K2 S4 120.38(4) . . ? S3 K2 S4 118.52(3) . . ? O2 K2 S1 96.30(5) . . ? S3 K2 S1 94.96(2) . . ? S4 K2 S1 81.83(2) . . ? O2 K2 S1 81.43(5) . 1_655 ? S3 K2 S1 94.62(2) . 1_655 ? S4 K2 S1 90.80(2) . 1_655 ? S1 K2 S1 169.91(3) . 1_655 ? O2 K2 K1 103.57(5) . 1_655 ? S3 K2 K1 49.865(18) . 1_655 ? S4 K2 K1 111.30(2) . 1_655 ? S1 K2 K1 144.78(2) . 1_655 ? S1 K2 K1 44.775(17) 1_655 1_655 ? O2 K2 H1B 80.8 . . ? S3 K2 H1B 77.1 . . ? S4 K2 H1B 116.1 . . ? S1 K2 H1B 34.4 . . ? S1 K2 H1B 152.7 1_655 . ? K1 K2 H1B 121.1 1_655 . ? O1 K1 S1 114.43(4) . . ? O1 K1 S2 130.01(4) . . ? S1 K1 S2 115.27(3) . . ? O1 K1 S3 98.68(5) . 1_455 ? S1 K1 S3 97.06(2) . 1_455 ? S2 K1 S3 80.30(2) . 1_455 ? O1 K1 S3 77.60(5) . . ? S1 K1 S3 92.16(2) . . ? S2 K1 S3 95.55(3) . . ? S3 K1 S3 170.78(3) 1_455 . ? O1 K1 H2B 59.0 . . ? S1 K1 H2B 66.2 . . ? S2 K1 H2B 143.2 . . ? S3 K1 H2B 136.4 1_455 . ? S3 K1 H2B 48.6 . . ? O1 K1 K2 115.46(5) . 1_455 ? S1 K1 K2 52.324(19) . 1_455 ? S2 K1 K2 98.75(3) . 1_455 ? S3 K1 K2 44.754(17) 1_455 1_455 ? S3 K1 K2 144.45(2) . 1_455 ? H2B K1 K2 107.6 . 1_455 ? C1 N1 C2 108.53(18) . . ? C1 N1 B1 126.26(18) . . ? C2 N1 B1 125.17(18) . . ? C1 N2 C3 109.74(18) . . ? C1 N2 C4 124.35(19) . . ? C3 N2 C4 125.87(19) . . ? C5 N3 C6 108.22(19) . . ? C5 N3 B1 126.45(18) . . ? C6 N3 B1 125.22(18) . . ? C5 N4 C7 109.98(19) . . ? C5 N4 C8 125.4(2) . . ? C7 N4 C8 124.4(2) . . ? C9 N5 N6 110.14(18) . . ? C9 N5 B1 134.47(19) . . ? N6 N5 B1 114.21(17) . . ? C11 N6 N5 106.69(18) . . ? C14 N7 C15 108.06(18) . . ? C14 N7 B2 126.91(18) . . ? C15 N7 B2 124.97(18) . . ? C14 N8 C16 109.09(19) . . ? C14 N8 C17 125.0(2) . . ? C16 N8 C17 125.8(2) . . ? C18 N9 C19 108.02(19) . . ? C18 N9 B2 127.64(19) . . ? C19 N9 B2 124.08(19) . . ? C18 N10 C20 110.06(19) . . ? C18 N10 C21 125.16(19) . . ? C20 N10 C21 124.73(19) . . ? C22 N11 N12 109.81(18) . . ? C22 N11 B2 135.93(19) . . ? N12 N11 B2 113.89(17) . . ? C24 N12 N11 106.21(18) . . ? C28 O2 K2 128.43(15) . . ? C28 O2 H2O 106(2) . . ? K2 O2 H2O 118(2) . . ? C27 O1 K1 125.66(16) . . ? C27 O1 H1O 108(2) . . ? K1 O1 H1O 119(2) . . ? C1 S1 K1 116.09(8) . . ? C1 S1 K2 83.19(8) . . ? K1 S1 K2 87.44(2) . . ? C1 S1 K2 98.41(8) . 1_455 ? K1 S1 K2 82.90(2) . 1_455 ? K2 S1 K2 169.90(3) . 1_455 ? C5 S2 K1 73.78(8) . . ? C14 S3 K2 113.93(8) . . ? C14 S3 K1 81.76(8) . 1_655 ? K2 S3 K1 85.38(2) . 1_655 ? C14 S3 K1 101.59(8) . . ? K2 S3 K1 85.41(2) . . ? K1 S3 K1 170.78(3) 1_655 . ? C18 S4 K2 76.18(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.1(3) . . . . ? N3 C6 C7 N4 -0.3(2) . . . . ? N5 C9 C10 C11 -0.9(3) . . . . ? C12 C9 C10 C11 -179.7(2) . . . . ? C9 C10 C11 N6 0.6(3) . . . . ? C9 C10 C11 C13 -179.1(2) . . . . ? N7 C15 C16 N8 0.5(3) . . . . ? N9 C19 C20 N10 -0.2(2) . . . . ? N11 C22 C23 C24 -0.4(3) . . . . ? C25 C22 C23 C24 -178.1(2) . . . . ? C22 C23 C24 N12 -0.1(3) . . . . ? C22 C23 C24 C26 179.2(2) . . . . ? N2 C1 N1 C2 0.5(2) . . . . ? S1 C1 N1 C2 179.65(18) . . . . ? N2 C1 N1 B1 178.23(19) . . . . ? S1 C1 N1 B1 -2.6(3) . . . . ? C3 C2 N1 C1 -0.2(3) . . . . ? C3 C2 N1 B1 -178.0(2) . . . . ? N3 B1 N1 C1 86.4(3) . . . . ? N5 B1 N1 C1 -154.2(2) . . . . ? N3 B1 N1 C2 -96.2(2) . . . . ? N5 B1 N1 C2 23.2(3) . . . . ? N1 C1 N2 C3 -0.5(2) . . . . ? S1 C1 N2 C3 -179.77(16) . . . . ? N1 C1 N2 C4 -178.4(2) . . . . ? S1 C1 N2 C4 2.3(3) . . . . ? C2 C3 N2 C1 0.4(3) . . . . ? C2 C3 N2 C4 178.2(2) . . . . ? N4 C5 N3 C6 -0.4(2) . . . . ? S2 C5 N3 C6 -179.50(17) . . . . ? N4 C5 N3 B1 -176.49(19) . . . . ? S2 C5 N3 B1 4.4(3) . . . . ? C7 C6 N3 C5 0.4(2) . . . . ? C7 C6 N3 B1 176.61(19) . . . . ? N5 B1 N3 C5 80.1(3) . . . . ? N1 B1 N3 C5 -164.55(19) . . . . ? N5 B1 N3 C6 -95.4(2) . . . . ? N1 B1 N3 C6 20.0(3) . . . . ? N3 C5 N4 C7 0.2(2) . . . . ? S2 C5 N4 C7 179.33(17) . . . . ? N3 C5 N4 C8 -174.9(2) . . . . ? S2 C5 N4 C8 4.3(3) . . . . ? C6 C7 N4 C5 0.1(2) . . . . ? C6 C7 N4 C8 175.2(2) . . . . ? C10 C9 N5 N6 0.8(2) . . . . ? C12 C9 N5 N6 179.6(2) . . . . ? C10 C9 N5 B1 167.2(2) . . . . ? C12 C9 N5 B1 -13.9(4) . . . . ? N3 B1 N5 C9 16.7(3) . . . . ? N1 B1 N5 C9 -100.4(3) . . . . ? N3 B1 N5 N6 -177.30(17) . . . . ? N1 B1 N5 N6 65.6(2) . . . . ? C10 C11 N6 N5 -0.1(3) . . . . ? C13 C11 N6 N5 179.6(2) . . . . ? C9 N5 N6 C11 -0.4(2) . . . . ? B1 N5 N6 C11 -169.83(18) . . . . ? N8 C14 N7 C15 0.3(2) . . . . ? S3 C14 N7 C15 179.11(18) . . . . ? N8 C14 N7 B2 177.51(19) . . . . ? S3 C14 N7 B2 -3.7(3) . . . . ? C16 C15 N7 C14 -0.5(3) . . . . ? C16 C15 N7 B2 -177.8(2) . . . . ? N9 B2 N7 C14 92.1(2) . . . . ? N11 B2 N7 C14 -148.4(2) . . . . ? N9 B2 N7 C15 -91.2(2) . . . . ? N11 B2 N7 C15 28.4(3) . . . . ? N7 C14 N8 C16 0.0(2) . . . . ? S3 C14 N8 C16 -178.89(16) . . . . ? N7 C14 N8 C17 -176.0(2) . . . . ? S3 C14 N8 C17 5.1(3) . . . . ? C15 C16 N8 C14 -0.3(3) . . . . ? C15 C16 N8 C17 175.7(2) . . . . ? N10 C18 N9 C19 0.5(2) . . . . ? S4 C18 N9 C19 -179.62(17) . . . . ? N10 C18 N9 B2 -173.76(19) . . . . ? S4 C18 N9 B2 6.2(3) . . . . ? C20 C19 N9 C18 -0.2(2) . . . . ? C20 C19 N9 B2 174.32(19) . . . . ? N11 B2 N9 C18 79.7(3) . . . . ? N7 B2 N9 C18 -164.46(19) . . . . ? N11 B2 N9 C19 -93.6(2) . . . . ? N7 B2 N9 C19 22.2(3) . . . . ? N9 C18 N10 C20 -0.6(2) . . . . ? S4 C18 N10 C20 179.48(16) . . . . ? N9 C18 N10 C21 -178.2(2) . . . . ? S4 C18 N10 C21 1.9(3) . . . . ? C19 C20 N10 C18 0.5(3) . . . . ? C19 C20 N10 C21 178.1(2) . . . . ? C23 C22 N11 N12 0.7(3) . . . . ? C25 C22 N11 N12 178.5(2) . . . . ? C23 C22 N11 B2 173.0(2) . . . . ? C25 C22 N11 B2 -9.2(4) . . . . ? N9 B2 N11 C22 6.7(3) . . . . ? N7 B2 N11 C22 -111.0(3) . . . . ? N9 B2 N11 N12 178.74(17) . . . . ? N7 B2 N11 N12 61.1(2) . . . . ? C23 C24 N12 N11 0.5(3) . . . . ? C26 C24 N12 N11 -178.9(2) . . . . ? C22 N11 N12 C24 -0.8(2) . . . . ? B2 N11 N12 C24 -174.89(18) . . . . ? S3 K2 O2 C28 165.02(17) . . . . ? S4 K2 O2 C28 -11.1(2) . . . . ? S1 K2 O2 C28 -95.32(18) . . . . ? S1 K2 O2 C28 74.76(18) 1_655 . . . ? K1 K2 O2 C28 113.96(18) 1_655 . . . ? H1B K2 O2 C28 -126.1 . . . . ? S1 K1 O1 C27 162.80(17) . . . . ? S2 K1 O1 C27 -10.7(2) . . . . ? S3 K1 O1 C27 -95.32(18) 1_455 . . . ? S3 K1 O1 C27 76.10(18) . . . . ? H2B K1 O1 C27 124.9 . . . . ? K2 K1 O1 C27 -139.02(18) 1_455 . . . ? N1 C1 S1 K1 -15.7(2) . . . . ? N2 C1 S1 K1 163.34(16) . . . . ? N1 C1 S1 K2 -99.5(2) . . . . ? N2 C1 S1 K2 79.57(18) . . . . ? N1 C1 S1 K2 70.4(2) . . . 1_455 ? N2 C1 S1 K2 -110.49(18) . . . 1_455 ? O1 K1 S1 C1 -159.86(9) . . . . ? S2 K1 S1 C1 14.66(9) . . . . ? S3 K1 S1 C1 97.24(9) 1_455 . . . ? S3 K1 S1 C1 -82.51(9) . . . . ? H2B K1 S1 C1 -124.8 . . . . ? K2 K1 S1 C1 95.92(9) 1_455 . . . ? O1 K1 S1 K2 -78.72(5) . . . . ? S2 K1 S1 K2 95.80(3) . . . . ? S3 K1 S1 K2 178.381(17) 1_455 . . . ? S3 K1 S1 K2 -1.370(17) . . . . ? H2B K1 S1 K2 -43.6 . . . . ? K2 K1 S1 K2 177.06(2) 1_455 . . . ? O1 K1 S1 K2 104.22(5) . . . 1_455 ? S2 K1 S1 K2 -81.26(3) . . . 1_455 ? S3 K1 S1 K2 1.320(17) 1_455 . . 1_455 ? S3 K1 S1 K2 -178.431(17) . . . 1_455 ? H2B K1 S1 K2 139.3 . . . 1_455 ? O2 K2 S1 C1 -3.77(9) . . . . ? S3 K2 S1 C1 118.21(8) . . . . ? S4 K2 S1 C1 -123.65(8) . . . . ? S1 K2 S1 C1 -80.21(16) 1_655 . . . ? K1 K2 S1 C1 120.69(8) 1_655 . . . ? H1B K2 S1 C1 59.8 . . . . ? O2 K2 S1 K1 -120.43(4) . . . . ? S3 K2 S1 K1 1.552(19) . . . . ? S4 K2 S1 K1 119.69(2) . . . . ? S1 K2 S1 K1 163.14(13) 1_655 . . . ? K1 K2 S1 K1 4.03(3) 1_655 . . . ? H1B K2 S1 K1 -56.9 . . . . ? O2 K2 S1 K2 -103.55(14) . . . 1_455 ? S3 K2 S1 K2 18.42(14) . . . 1_455 ? S4 K2 S1 K2 136.57(13) . . . 1_455 ? S1 K2 S1 K2 -179.992(2) 1_655 . . 1_455 ? K1 K2 S1 K2 20.90(16) 1_655 . . 1_455 ? H1B K2 S1 K2 -40.0 . . . 1_455 ? N4 C5 S2 K1 -106.3(2) . . . . ? N3 C5 S2 K1 72.63(19) . . . . ? O1 K1 S2 C5 119.08(10) . . . . ? S1 K1 S2 C5 -54.41(8) . . . . ? S3 K1 S2 C5 -147.69(8) 1_455 . . . ? S3 K1 S2 C5 40.62(8) . . . . ? H2B K1 S2 C5 29.1 . . . . ? K2 K1 S2 C5 -106.74(8) 1_455 . . . ? N7 C14 S3 K2 -16.5(2) . . . . ? N8 C14 S3 K2 162.15(16) . . . . ? N7 C14 S3 K1 -97.7(2) . . . 1_655 ? N8 C14 S3 K1 80.96(19) . . . 1_655 ? N7 C14 S3 K1 73.6(2) . . . . ? N8 C14 S3 K1 -107.76(19) . . . . ? O2 K2 S3 C14 -160.32(9) . . . . ? S4 K2 S3 C14 15.89(9) . . . . ? S1 K2 S3 C14 99.27(9) . . . . ? S1 K2 S3 C14 -77.55(9) 1_655 . . . ? K1 K2 S3 C14 -78.86(9) 1_655 . . . ? H1B K2 S3 C14 128.9 . . . . ? O2 K2 S3 K1 -81.46(6) . . . 1_655 ? S4 K2 S3 K1 94.75(4) . . . 1_655 ? S1 K2 S3 K1 178.130(17) . . . 1_655 ? S1 K2 S3 K1 1.314(17) 1_655 . . 1_655 ? H1B K2 S3 K1 -152.3 . . . 1_655 ? O2 K2 S3 K1 99.03(6) . . . . ? S4 K2 S3 K1 -84.77(4) . . . . ? S1 K2 S3 K1 -1.383(17) . . . . ? S1 K2 S3 K1 -178.199(17) 1_655 . . . ? K1 K2 S3 K1 -179.51(2) 1_655 . . . ? H1B K2 S3 K1 28.2 . . . . ? O1 K1 S3 C14 2.54(9) . . . . ? S1 K1 S3 C14 -112.02(8) . . . . ? S2 K1 S3 C14 132.33(8) . . . . ? S3 K1 S3 C14 69.53(17) 1_455 . . . ? H2B K1 S3 C14 -56.9 . . . . ? K2 K1 S3 C14 -114.15(8) 1_455 . . . ? O1 K1 S3 K2 116.05(4) . . . . ? S1 K1 S3 K2 1.494(18) . . . . ? S2 K1 S3 K2 -114.16(2) . . . . ? S3 K1 S3 K2 -176.96(14) 1_455 . . . ? H2B K1 S3 K2 56.6 . . . . ? K2 K1 S3 K2 -0.64(3) 1_455 . . . ? O1 K1 S3 K1 113.02(15) . . . 1_655 ? S1 K1 S3 K1 -1.54(16) . . . 1_655 ? S2 K1 S3 K1 -117.19(15) . . . 1_655 ? S3 K1 S3 K1 -179.989(1) 1_455 . . 1_655 ? H2B K1 S3 K1 53.6 . . . 1_655 ? K2 K1 S3 K1 -3.67(17) 1_455 . . 1_655 ? N9 C18 S4 K2 67.18(19) . . . . ? N10 C18 S4 K2 -112.92(19) . . . . ? O2 K2 S4 C18 123.43(9) . . . . ? S3 K2 S4 C18 -52.80(8) . . . . ? S1 K2 S4 C18 -144.02(8) . . . . ? S1 K2 S4 C18 42.90(8) 1_655 . . . ? K1 K2 S4 C18 2.07(8) 1_655 . . . ? H1B K2 S4 C18 -141.9 . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.436 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.073 data_2 _database_code_depnum_ccdc_archive 'CCDC 803998' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 B K N6 S2, 0.5(C H4 O)' _chemical_formula_sum 'C11.50 H16 B K N6 O0.50 S2' _chemical_formula_weight 360.33 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8712(2) _cell_length_b 12.5318(3) _cell_length_c 13.7319(3) _cell_angle_alpha 113.484(1) _cell_angle_beta 100.682(1) _cell_angle_gamma 94.266(1) _cell_volume 1663.12(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 0.576 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6581 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_reflns_number 35085 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.53 _reflns_number_total 7636 _reflns_number_gt 5827 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0666P)^2^+0.9321P] 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 7636 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1313 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 B1 B 1.19016(19) 0.6307(2) 0.44081(17) 0.0131(4) Uani 1 1 d . . . H1B H 1.1533 0.5717 0.4641 0.016 Uiso 1 1 calc R . . B2 B 0.68131(19) 0.1318(2) -0.05329(17) 0.0126(4) Uani 1 1 d . . . H2B H 0.6450 0.0716 -0.0312 0.015 Uiso 1 1 calc R . . C1 C 1.03705(18) 0.77304(18) 0.51865(16) 0.0147(4) Uani 1 1 d . . . C2 C 1.23673(19) 0.86112(18) 0.55477(17) 0.0191(4) Uani 1 1 d . . . H2 H 1.3247 0.8726 0.5569 0.023 Uiso 1 1 calc R . . C3 C 1.1701(2) 0.9464(2) 0.60061(18) 0.0228(5) Uani 1 1 d . . . H3 H 1.2020 1.0282 0.6413 0.027 Uiso 1 1 calc R . . C4 C 0.9420(2) 0.9495(2) 0.6163(2) 0.0280(5) Uani 1 1 d . . . H4A H 0.8613 0.9064 0.5645 0.042 Uiso 1 1 calc R . . H4B H 0.9543 1.0306 0.6230 0.042 Uiso 1 1 calc R . . H4C H 0.9408 0.9505 0.6878 0.042 Uiso 1 1 calc R . . C5 C 1.41226(17) 0.64116(17) 0.55542(16) 0.0135(4) Uani 1 1 d . . . C6 C 1.41371(18) 0.65361(18) 0.39800(16) 0.0167(4) Uani 1 1 d . . . H6 H 1.3855 0.6571 0.3297 0.020 Uiso 1 1 calc R . . C7 C 1.53553(19) 0.65878(18) 0.44682(17) 0.0177(4) Uani 1 1 d . . . H7 H 1.6083 0.6663 0.4195 0.021 Uiso 1 1 calc R . . C8 C 1.64498(19) 0.6577(2) 0.62521(18) 0.0222(5) Uani 1 1 d . . . H8A H 1.6621 0.7355 0.6871 0.033 Uiso 1 1 calc R . . H8B H 1.7184 0.6459 0.5924 0.033 Uiso 1 1 calc R . . H8C H 1.6293 0.5964 0.6508 0.033 Uiso 1 1 calc R . . C9 C 1.1309(2) 0.6573(2) 0.25907(17) 0.0225(5) Uani 1 1 d . . . H9 H 1.1443 0.7411 0.2890 0.027 Uiso 1 1 calc R . . C10 C 1.0994(2) 0.5821(2) 0.14928(18) 0.0242(5) Uani 1 1 d . . . H10 H 1.0869 0.6024 0.0889 0.029 Uiso 1 1 calc R . . C11 C 1.08991(19) 0.46956(19) 0.14730(17) 0.0195(4) Uani 1 1 d . . . H11 H 1.0686 0.3985 0.0823 0.023 Uiso 1 1 calc R . . C12 C 0.52197(18) 0.26891(18) 0.01983(16) 0.0145(4) Uani 1 1 d . . . C13 C 0.7203(2) 0.36257(18) 0.06531(17) 0.0198(4) Uani 1 1 d . . . H13 H 0.8090 0.3773 0.0714 0.024 Uiso 1 1 calc R . . C14 C 0.6484(2) 0.4439(2) 0.10926(18) 0.0239(5) Uani 1 1 d . . . H14 H 0.6771 0.5259 0.1523 0.029 Uiso 1 1 calc R . . C15 C 0.4181(2) 0.4399(2) 0.1150(2) 0.0298(5) Uani 1 1 d . . . H15A H 0.3409 0.4014 0.0567 0.045 Uiso 1 1 calc R . . H15B H 0.4339 0.5240 0.1311 0.045 Uiso 1 1 calc R . . H15C H 0.4073 0.4310 0.1808 0.045 Uiso 1 1 calc R . . C16 C 0.90232(17) 0.14195(17) 0.06254(15) 0.0130(4) Uani 1 1 d . . . C17 C 0.90497(18) 0.15364(18) -0.09533(16) 0.0159(4) Uani 1 1 d . . . H17 H 0.8773 0.1574 -0.1635 0.019 Uiso 1 1 calc R . . C18 C 1.02617(19) 0.15525(18) -0.04736(17) 0.0168(4) Uani 1 1 d . . . H18 H 1.0990 0.1602 -0.0754 0.020 Uiso 1 1 calc R . . C19 C 1.13484(18) 0.1536(2) 0.13094(18) 0.0209(4) Uani 1 1 d . . . H19A H 1.1519 0.2306 0.1938 0.031 Uiso 1 1 calc R . . H19B H 1.2084 0.1426 0.0982 0.031 Uiso 1 1 calc R . . H19C H 1.1189 0.0911 0.1551 0.031 Uiso 1 1 calc R . . C20 C 0.5981(2) 0.1564(2) -0.23410(18) 0.0254(5) Uani 1 1 d . . . H20 H 0.5915 0.2378 -0.2036 0.031 Uiso 1 1 calc R . . C21 C 0.5745(2) 0.0834(2) -0.34381(18) 0.0295(5) Uani 1 1 d . . . H21 H 0.5487 0.1031 -0.4037 0.035 Uiso 1 1 calc R . . C22 C 0.5970(2) -0.02610(19) -0.34703(17) 0.0196(4) Uani 1 1 d . . . H22 H 0.5887 -0.0952 -0.4124 0.024 Uiso 1 1 calc R . . K1 K 0.92944(4) 0.39924(4) 0.34096(4) 0.01779(12) Uani 1 1 d . . . K2 K 0.43785(4) -0.10338(4) -0.16422(4) 0.01734(12) Uani 1 1 d . . . N1 N 1.15524(15) 0.75335(15) 0.50369(13) 0.0145(3) Uani 1 1 d . . . N2 N 1.04575(17) 0.89152(16) 0.57692(14) 0.0193(4) Uani 1 1 d . . . N3 N 1.33692(15) 0.64233(14) 0.46509(13) 0.0135(3) Uani 1 1 d . . . N4 N 1.53352(15) 0.65093(15) 0.54391(14) 0.0154(3) Uani 1 1 d . . . N5 N 1.13943(14) 0.59124(14) 0.31671(13) 0.0130(3) Uani 1 1 d . . . N6 N 1.11445(16) 0.47385(15) 0.24771(14) 0.0177(4) Uani 1 1 d . . . N7 N 0.64196(15) 0.25328(14) 0.00944(13) 0.0138(3) Uani 1 1 d . . . N8 N 0.52506(17) 0.38576(16) 0.07993(14) 0.0192(4) Uani 1 1 d . . . N9 N 0.82802(14) 0.14552(14) -0.02720(13) 0.0130(3) Uani 1 1 d . . . N10 N 1.02347(15) 0.14839(15) 0.05003(13) 0.0149(3) Uani 1 1 d . . . N11 N 0.63243(14) 0.09272(14) -0.17737(13) 0.0125(3) Uani 1 1 d . . . N12 N 0.63160(16) -0.02146(15) -0.24690(14) 0.0172(4) Uani 1 1 d . . . S1 S 0.90363(5) 0.67097(5) 0.47582(4) 0.01879(13) Uani 1 1 d . . . S2 S 1.36789(4) 0.63025(5) 0.66427(4) 0.01594(13) Uani 1 1 d . . . S3 S 0.39010(4) 0.16276(5) -0.03057(4) 0.01846(13) Uani 1 1 d . . . S4 S 0.85776(4) 0.13128(5) 0.17110(4) 0.01574(13) Uani 1 1 d . . . C23 C 0.8275(2) 0.7270(2) 0.2171(2) 0.0394(6) Uani 1 1 d . . . H23A H 0.8812 0.8004 0.2314 0.059 Uiso 1 1 calc R . . H23B H 0.8243 0.6684 0.1431 0.059 Uiso 1 1 calc R . . H23C H 0.8628 0.6970 0.2703 0.059 Uiso 1 1 calc R . . O1 O 0.70431(19) 0.74883(19) 0.22622(18) 0.0470(5) Uani 1 1 d . . . H1A H 0.6766 0.7803 0.1846 0.070 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 B1 0.0108(9) 0.0150(11) 0.0099(10) 0.0029(9) 0.0000(8) 0.0003(8) B2 0.0105(9) 0.0140(11) 0.0107(10) 0.0034(9) 0.0012(8) -0.0005(8) C1 0.0167(9) 0.0175(10) 0.0122(9) 0.0077(8) 0.0044(7) 0.0064(8) C2 0.0190(10) 0.0151(11) 0.0188(10) 0.0040(9) 0.0030(8) -0.0019(8) C3 0.0266(11) 0.0142(11) 0.0225(11) 0.0034(9) 0.0045(9) 0.0017(8) C4 0.0310(12) 0.0259(13) 0.0290(12) 0.0086(11) 0.0137(10) 0.0165(10) C5 0.0121(9) 0.0097(9) 0.0146(9) 0.0017(8) 0.0016(7) 0.0019(7) C6 0.0181(10) 0.0168(11) 0.0152(10) 0.0055(8) 0.0066(8) 0.0034(8) C7 0.0167(10) 0.0165(11) 0.0191(10) 0.0050(9) 0.0081(8) 0.0027(8) C8 0.0126(9) 0.0251(12) 0.0247(11) 0.0082(10) 0.0000(8) 0.0036(8) C9 0.0321(12) 0.0166(11) 0.0184(11) 0.0087(9) 0.0017(9) 0.0046(9) C10 0.0318(12) 0.0241(12) 0.0162(10) 0.0102(10) 0.0010(9) 0.0031(9) C11 0.0217(10) 0.0178(11) 0.0124(10) 0.0009(8) 0.0021(8) 0.0008(8) C12 0.0176(9) 0.0147(10) 0.0130(9) 0.0070(8) 0.0047(7) 0.0041(7) C13 0.0207(10) 0.0144(11) 0.0198(10) 0.0043(9) 0.0034(8) -0.0030(8) C14 0.0317(12) 0.0123(11) 0.0225(11) 0.0030(9) 0.0064(9) -0.0010(9) C15 0.0382(13) 0.0241(13) 0.0303(13) 0.0090(11) 0.0161(11) 0.0191(10) C16 0.0119(9) 0.0106(10) 0.0136(9) 0.0028(8) 0.0016(7) 0.0007(7) C17 0.0160(9) 0.0164(10) 0.0157(10) 0.0062(8) 0.0067(8) 0.0007(8) C18 0.0162(9) 0.0154(10) 0.0192(10) 0.0061(9) 0.0082(8) 0.0008(8) C19 0.0118(9) 0.0245(12) 0.0245(11) 0.0105(10) -0.0001(8) 0.0026(8) C20 0.0394(13) 0.0178(12) 0.0175(11) 0.0086(9) -0.0001(9) 0.0053(9) C21 0.0449(14) 0.0248(13) 0.0170(11) 0.0110(10) -0.0013(10) 0.0041(10) C22 0.0228(10) 0.0189(11) 0.0125(10) 0.0025(9) 0.0039(8) -0.0003(8) K1 0.0167(2) 0.0175(2) 0.0158(2) 0.00470(19) 0.00348(17) -0.00187(17) K2 0.0155(2) 0.0161(2) 0.0167(2) 0.00374(19) 0.00391(17) -0.00117(17) N1 0.0136(8) 0.0138(9) 0.0136(8) 0.0039(7) 0.0017(6) 0.0015(6) N2 0.0229(9) 0.0164(9) 0.0180(9) 0.0055(8) 0.0061(7) 0.0072(7) N3 0.0121(8) 0.0133(9) 0.0130(8) 0.0038(7) 0.0026(6) 0.0006(6) N4 0.0126(8) 0.0143(9) 0.0159(8) 0.0036(7) 0.0018(6) 0.0012(6) N5 0.0123(7) 0.0112(8) 0.0120(8) 0.0022(7) 0.0014(6) 0.0010(6) N6 0.0215(9) 0.0128(9) 0.0145(8) 0.0025(7) 0.0028(7) -0.0004(7) N7 0.0135(8) 0.0121(8) 0.0142(8) 0.0045(7) 0.0024(6) 0.0005(6) N8 0.0249(9) 0.0145(9) 0.0187(9) 0.0056(7) 0.0075(7) 0.0082(7) N9 0.0113(7) 0.0136(9) 0.0129(8) 0.0048(7) 0.0024(6) 0.0003(6) N10 0.0104(7) 0.0149(9) 0.0169(8) 0.0044(7) 0.0027(6) 0.0011(6) N11 0.0116(7) 0.0123(8) 0.0120(8) 0.0041(7) 0.0019(6) 0.0009(6) N12 0.0228(9) 0.0115(9) 0.0145(8) 0.0026(7) 0.0042(7) 0.0030(7) S1 0.0124(2) 0.0217(3) 0.0228(3) 0.0094(2) 0.0054(2) 0.00310(19) S2 0.0155(2) 0.0182(3) 0.0125(2) 0.0055(2) 0.00223(18) 0.00180(19) S3 0.0119(2) 0.0200(3) 0.0241(3) 0.0093(2) 0.0052(2) 0.00358(19) S4 0.0143(2) 0.0193(3) 0.0123(2) 0.0059(2) 0.00222(18) 0.00133(19) C23 0.0320(13) 0.0361(16) 0.0455(16) 0.0189(13) -0.0033(12) -0.0008(11) O1 0.0426(11) 0.0456(13) 0.0573(13) 0.0272(11) 0.0086(10) 0.0097(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 N5 1.547(3) . ? B1 N1 1.550(3) . ? B1 N3 1.552(2) . ? B1 H1B 1.0000 . ? B2 N11 1.545(3) . ? B2 N9 1.549(2) . ? B2 N7 1.559(3) . ? B2 K2 3.432(2) . ? B2 H2B 1.0000 . ? C1 N1 1.363(2) . ? C1 N2 1.363(3) . ? C1 S1 1.701(2) . ? C1 K1 3.418(2) 2_766 ? C2 C3 1.346(3) . ? C2 N1 1.392(3) . ? C2 H2 0.9500 . ? C3 N2 1.388(3) . ? C3 H3 0.9500 . ? C4 N2 1.458(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N4 1.359(2) . ? C5 N3 1.360(2) . ? C5 S2 1.705(2) . ? C6 C7 1.353(3) . ? C6 N3 1.392(2) . ? C6 H6 0.9500 . ? C7 N4 1.379(3) . ? C7 H7 0.9500 . ? C8 N4 1.459(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 N5 1.352(3) . ? C9 C10 1.381(3) . ? C9 H9 0.9500 . ? C10 C11 1.396(3) . ? C10 H10 0.9500 . ? C11 N6 1.333(3) . ? C11 H11 0.9500 . ? C12 N7 1.358(2) . ? C12 N8 1.359(3) . ? C12 S3 1.708(2) . ? C12 K2 3.394(2) 2_655 ? C13 C14 1.349(3) . ? C13 N7 1.392(3) . ? C13 H13 0.9500 . ? C14 N8 1.383(3) . ? C14 H14 0.9500 . ? C15 N8 1.452(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N10 1.360(2) . ? C16 N9 1.361(2) . ? C16 S4 1.7006(19) . ? C17 C18 1.354(3) . ? C17 N9 1.392(2) . ? C17 H17 0.9500 . ? C18 N10 1.379(3) . ? C18 H18 0.9500 . ? C19 N10 1.462(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N11 1.347(3) . ? C20 C21 1.377(3) . ? C20 H20 0.9500 . ? C21 C22 1.397(3) . ? C21 H21 0.9500 . ? C22 N12 1.333(3) . ? C22 H22 0.9500 . ? K1 N6 2.8615(17) . ? K1 S4 3.1652(7) . ? K1 S2 3.2101(6) 2_766 ? K1 S1 3.2269(7) . ? K1 S1 3.2720(7) 2_766 ? K1 N5 3.3489(16) . ? K1 C1 3.418(2) 2_766 ? K2 N12 2.8764(17) . ? K2 S2 3.1560(7) 1_444 ? K2 S4 3.1863(6) 2_655 ? K2 N11 3.2045(16) . ? K2 S3 3.2394(7) . ? K2 S3 3.3385(7) 2_655 ? K2 C12 3.394(2) 2_655 ? N5 N6 1.367(2) . ? N11 N12 1.366(2) . ? S1 K1 3.2721(7) 2_766 ? S2 K2 3.1561(7) 1_666 ? S2 K1 3.2101(6) 2_766 ? S3 K2 3.3385(7) 2_655 ? S4 K2 3.1863(6) 2_655 ? C23 O1 1.404(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O1 H1A 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 B1 N1 109.25(16) . . ? N5 B1 N3 108.28(15) . . ? N1 B1 N3 108.38(15) . . ? N5 B1 K1 70.39(9) . . ? N1 B1 K1 112.87(11) . . ? N3 B1 K1 136.55(13) . . ? N5 B1 H1B 110.3 . . ? N1 B1 H1B 110.3 . . ? N3 B1 H1B 110.3 . . ? N11 B2 N9 108.31(15) . . ? N11 B2 N7 109.17(16) . . ? N9 B2 N7 109.10(15) . . ? N11 B2 K2 68.43(9) . . ? N9 B2 K2 134.66(13) . . ? N7 B2 K2 114.55(11) . . ? N11 B2 H2B 110.1 . . ? N9 B2 H2B 110.1 . . ? N7 B2 H2B 110.1 . . ? N1 C1 N2 106.77(17) . . ? N1 C1 S1 127.42(16) . . ? N2 C1 S1 125.80(15) . . ? N1 C1 K1 85.26(11) . 2_766 ? N2 C1 K1 118.09(12) . 2_766 ? S1 C1 K1 70.56(7) . 2_766 ? C3 C2 N1 108.65(18) . . ? C3 C2 H2 125.7 . . ? N1 C2 H2 125.7 . . ? C2 C3 N2 106.63(19) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N4 C5 N3 106.84(16) . . ? N4 C5 S2 125.10(15) . . ? N3 C5 S2 128.06(14) . . ? C7 C6 N3 108.19(18) . . ? C7 C6 H6 125.9 . . ? N3 C6 H6 125.9 . . ? C6 C7 N4 106.67(17) . . ? C6 C7 H7 126.7 . . ? N4 C7 H7 126.7 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 C10 108.21(19) . . ? N5 C9 H9 125.9 . . ? C10 C9 H9 125.9 . . ? C9 C10 C11 104.25(19) . . ? C9 C10 H10 127.9 . . ? C11 C10 H10 127.9 . . ? N6 C11 C10 111.79(19) . . ? N6 C11 H11 124.1 . . ? C10 C11 H11 124.1 . . ? N7 C12 N8 107.45(17) . . ? N7 C12 S3 127.20(15) . . ? N8 C12 S3 125.35(15) . . ? N7 C12 K2 84.15(11) . 2_655 ? N8 C12 K2 115.47(12) . 2_655 ? S3 C12 K2 73.52(7) . 2_655 ? C14 C13 N7 108.12(18) . . ? C14 C13 H13 125.9 . . ? N7 C13 H13 125.9 . . ? C13 C14 N8 107.21(19) . . ? C13 C14 H14 126.4 . . ? N8 C14 H14 126.4 . . ? N8 C15 H15A 109.5 . . ? N8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N10 C16 N9 106.65(16) . . ? N10 C16 S4 124.96(15) . . ? N9 C16 S4 128.39(14) . . ? C18 C17 N9 108.04(17) . . ? C18 C17 H17 126.0 . . ? N9 C17 H17 126.0 . . ? C17 C18 N10 106.74(17) . . ? C17 C18 H18 126.6 . . ? N10 C18 H18 126.6 . . ? N10 C19 H19A 109.5 . . ? N10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N11 C20 C21 108.3(2) . . ? N11 C20 H20 125.8 . . ? C21 C20 H20 125.8 . . ? C20 C21 C22 104.32(19) . . ? C20 C21 H21 127.8 . . ? C22 C21 H21 127.8 . . ? N12 C22 C21 111.51(19) . . ? N12 C22 H22 124.2 . . ? C21 C22 H22 124.2 . . ? N6 K1 S4 98.40(4) . . ? N6 K1 S2 143.42(4) . 2_766 ? S4 K1 S2 82.928(16) . 2_766 ? N6 K1 S1 89.70(4) . . ? S4 K1 S1 160.352(19) . . ? S2 K1 S1 79.977(16) 2_766 . ? N6 K1 S1 104.11(4) . 2_766 ? S4 K1 S1 91.266(17) . 2_766 ? S2 K1 S1 112.423(17) 2_766 2_766 ? S1 K1 S1 104.148(17) . 2_766 ? N6 K1 N5 23.82(4) . . ? S4 K1 N5 122.16(3) . . ? S2 K1 N5 136.14(3) 2_766 . ? S1 K1 N5 66.65(3) . . ? S1 K1 N5 103.02(3) 2_766 . ? N6 K1 C1 127.17(5) . 2_766 ? S4 K1 C1 71.44(4) . 2_766 ? S2 K1 C1 88.15(3) 2_766 2_766 ? S1 K1 C1 117.36(4) . 2_766 ? S1 K1 C1 29.36(3) 2_766 2_766 ? N5 K1 C1 131.81(4) . 2_766 ? N6 K1 B1 44.96(5) . . ? S4 K1 B1 138.02(4) . . ? S2 K1 B1 137.85(4) 2_766 . ? S1 K1 B1 57.90(4) . . ? S1 K1 B1 81.92(4) 2_766 . ? N5 K1 B1 25.79(4) . . ? C1 K1 B1 111.17(5) 2_766 . ? N12 K2 S2 99.90(4) . 1_444 ? N12 K2 S4 144.69(4) . 2_655 ? S2 K2 S4 83.457(16) 1_444 2_655 ? N12 K2 N11 25.22(4) . . ? S2 K2 N11 124.71(3) 1_444 . ? S4 K2 N11 133.29(3) 2_655 . ? N12 K2 S3 91.87(4) . . ? S2 K2 S3 156.808(19) 1_444 . ? S4 K2 S3 75.538(16) 2_655 . ? N11 K2 S3 67.08(3) . . ? N12 K2 S3 101.83(4) . 2_655 ? S2 K2 S3 94.150(17) 1_444 2_655 ? S4 K2 S3 113.035(17) 2_655 2_655 ? N11 K2 S3 102.08(3) . 2_655 ? S3 K2 S3 102.965(16) . 2_655 ? N12 K2 C12 125.01(5) . 2_655 ? S2 K2 C12 73.32(4) 1_444 2_655 ? S4 K2 C12 89.81(3) 2_655 2_655 ? N11 K2 C12 131.03(5) . 2_655 ? S3 K2 C12 115.72(4) . 2_655 ? S3 K2 C12 29.39(3) 2_655 2_655 ? N12 K2 B2 45.82(5) . . ? S2 K2 B2 141.29(4) 1_444 . ? S4 K2 B2 134.24(4) 2_655 . ? N11 K2 B2 26.63(4) . . ? S3 K2 B2 58.70(4) . . ? S3 K2 B2 79.76(4) 2_655 . ? C12 K2 B2 109.00(5) 2_655 . ? C1 N1 C2 108.26(17) . . ? C1 N1 B1 124.85(16) . . ? C2 N1 B1 126.89(16) . . ? C1 N2 C3 109.68(17) . . ? C1 N2 C4 124.66(18) . . ? C3 N2 C4 125.44(19) . . ? C5 N3 C6 108.36(16) . . ? C5 N3 B1 125.44(16) . . ? C6 N3 B1 126.20(16) . . ? C5 N4 C7 109.95(16) . . ? C5 N4 C8 124.59(17) . . ? C7 N4 C8 125.40(17) . . ? C9 N5 N6 110.39(16) . . ? C9 N5 B1 129.05(17) . . ? N6 N5 B1 119.86(16) . . ? C9 N5 K1 133.53(13) . . ? N6 N5 K1 57.68(9) . . ? B1 N5 K1 83.83(10) . . ? C11 N6 N5 105.36(16) . . ? C11 N6 K1 124.16(13) . . ? N5 N6 K1 98.50(10) . . ? C12 N7 C13 108.12(17) . . ? C12 N7 B2 124.48(16) . . ? C13 N7 B2 127.40(16) . . ? C12 N8 C14 109.10(17) . . ? C12 N8 C15 125.58(19) . . ? C14 N8 C15 125.17(19) . . ? C16 N9 C17 108.53(15) . . ? C16 N9 B2 125.39(16) . . ? C17 N9 B2 125.88(16) . . ? C16 N10 C18 110.04(16) . . ? C16 N10 C19 124.69(17) . . ? C18 N10 C19 125.19(16) . . ? C20 N11 N12 110.42(16) . . ? C20 N11 B2 130.35(17) . . ? N12 N11 B2 118.95(15) . . ? C20 N11 K2 123.30(13) . . ? N12 N11 K2 63.83(9) . . ? B2 N11 K2 84.94(10) . . ? C22 N12 N11 105.43(16) . . ? C22 N12 K2 117.00(13) . . ? N11 N12 K2 90.95(10) . . ? C1 S1 K1 116.95(7) . . ? C1 S1 K1 80.09(7) . 2_766 ? K1 S1 K1 75.852(17) . 2_766 ? C5 S2 K2 100.33(7) . 1_666 ? C5 S2 K1 117.91(7) . 2_766 ? K2 S2 K1 96.653(17) 1_666 2_766 ? C12 S3 K2 115.07(7) . . ? C12 S3 K2 77.10(7) . 2_655 ? K2 S3 K2 77.035(16) . 2_655 ? C16 S4 K1 99.66(7) . . ? C16 S4 K2 117.48(7) . 2_655 ? K1 S4 K2 96.955(17) . 2_655 ? O1 C23 H23A 109.5 . . ? O1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C23 O1 H1A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.6(2) . . . . ? N3 C6 C7 N4 -0.1(2) . . . . ? N5 C9 C10 C11 0.2(2) . . . . ? C9 C10 C11 N6 -0.4(3) . . . . ? N7 C13 C14 N8 -0.6(2) . . . . ? N9 C17 C18 N10 -0.1(2) . . . . ? N11 C20 C21 C22 0.1(3) . . . . ? C20 C21 C22 N12 0.2(3) . . . . ? N5 B1 K1 N6 25.39(9) . . . . ? N1 B1 K1 N6 128.67(15) . . . . ? N3 B1 K1 N6 -70.81(17) . . . . ? N5 B1 K1 S4 61.91(12) . . . . ? N1 B1 K1 S4 165.19(9) . . . . ? N3 B1 K1 S4 -34.3(2) . . . . ? N5 B1 K1 S2 -100.56(10) . . . 2_766 ? N1 B1 K1 S2 2.71(16) . . . 2_766 ? N3 B1 K1 S2 163.24(14) . . . 2_766 ? N5 B1 K1 S1 -102.87(10) . . . . ? N1 B1 K1 S1 0.40(10) . . . . ? N3 B1 K1 S1 160.93(19) . . . . ? N5 B1 K1 S1 144.77(10) . . . 2_766 ? N1 B1 K1 S1 -111.96(12) . . . 2_766 ? N3 B1 K1 S1 48.57(17) . . . 2_766 ? N1 B1 K1 N5 103.28(17) . . . . ? N3 B1 K1 N5 -96.2(2) . . . . ? N5 B1 K1 C1 147.33(10) . . . 2_766 ? N1 B1 K1 C1 -109.40(12) . . . 2_766 ? N3 B1 K1 C1 51.13(18) . . . 2_766 ? N5 B1 K1 K1 -166.26(11) . . . 2_766 ? N1 B1 K1 K1 -62.98(11) . . . 2_766 ? N3 B1 K1 K1 97.54(18) . . . 2_766 ? N11 B2 K2 N12 28.81(9) . . . . ? N9 B2 K2 N12 -66.02(16) . . . . ? N7 B2 K2 N12 130.79(15) . . . . ? N11 B2 K2 S2 62.78(12) . . . 1_444 ? N9 B2 K2 S2 -32.1(2) . . . 1_444 ? N7 B2 K2 S2 164.77(9) . . . 1_444 ? N11 B2 K2 S4 -101.13(10) . . . 2_655 ? N9 B2 K2 S4 164.03(14) . . . 2_655 ? N7 B2 K2 S4 0.85(15) . . . 2_655 ? N9 B2 K2 N11 -94.83(19) . . . . ? N7 B2 K2 N11 101.98(17) . . . . ? N11 B2 K2 S3 -101.28(10) . . . . ? N9 B2 K2 S3 163.88(19) . . . . ? N7 B2 K2 S3 0.70(10) . . . . ? N11 B2 K2 S3 146.59(10) . . . 2_655 ? N9 B2 K2 S3 51.76(16) . . . 2_655 ? N7 B2 K2 S3 -111.43(12) . . . 2_655 ? N11 B2 K2 C12 149.58(10) . . . 2_655 ? N9 B2 K2 C12 54.75(18) . . . 2_655 ? N7 B2 K2 C12 -108.44(12) . . . 2_655 ? N11 B2 K2 K2 -164.58(12) . . . 2_655 ? N9 B2 K2 K2 100.58(17) . . . 2_655 ? N7 B2 K2 K2 -62.60(11) . . . 2_655 ? N2 C1 N1 C2 0.8(2) . . . . ? S1 C1 N1 C2 -178.22(15) . . . . ? K1 C1 N1 C2 -117.17(14) 2_766 . . . ? N2 C1 N1 B1 -179.63(16) . . . . ? S1 C1 N1 B1 1.4(3) . . . . ? K1 C1 N1 B1 62.43(17) 2_766 . . . ? C3 C2 N1 C1 -0.1(2) . . . . ? C3 C2 N1 B1 -179.67(19) . . . . ? N5 B1 N1 C1 75.1(2) . . . . ? N3 B1 N1 C1 -167.10(17) . . . . ? K1 B1 N1 C1 -1.1(2) . . . . ? N5 B1 N1 C2 -105.4(2) . . . . ? N3 B1 N1 C2 12.4(3) . . . . ? K1 B1 N1 C2 178.44(15) . . . . ? N1 C1 N2 C3 -1.2(2) . . . . ? S1 C1 N2 C3 177.84(16) . . . . ? K1 C1 N2 C3 92.44(17) 2_766 . . . ? N1 C1 N2 C4 -176.13(19) . . . . ? S1 C1 N2 C4 2.9(3) . . . . ? K1 C1 N2 C4 -82.5(2) 2_766 . . . ? C2 C3 N2 C1 1.1(2) . . . . ? C2 C3 N2 C4 176.0(2) . . . . ? N4 C5 N3 C6 -0.3(2) . . . . ? S2 C5 N3 C6 179.48(15) . . . . ? N4 C5 N3 B1 178.67(17) . . . . ? S2 C5 N3 B1 -1.5(3) . . . . ? C7 C6 N3 C5 0.3(2) . . . . ? C7 C6 N3 B1 -178.69(18) . . . . ? N5 B1 N3 C5 -159.72(17) . . . . ? N1 B1 N3 C5 81.9(2) . . . . ? K1 B1 N3 C5 -79.2(2) . . . . ? N5 B1 N3 C6 19.1(3) . . . . ? N1 B1 N3 C6 -99.3(2) . . . . ? K1 B1 N3 C6 99.6(2) . . . . ? N3 C5 N4 C7 0.2(2) . . . . ? S2 C5 N4 C7 -179.56(15) . . . . ? N3 C5 N4 C8 177.53(18) . . . . ? S2 C5 N4 C8 -2.3(3) . . . . ? C6 C7 N4 C5 -0.1(2) . . . . ? C6 C7 N4 C8 -177.33(19) . . . . ? C10 C9 N5 N6 0.1(2) . . . . ? C10 C9 N5 B1 170.34(18) . . . . ? C10 C9 N5 K1 -64.2(2) . . . . ? N1 B1 N5 C9 35.3(3) . . . . ? N3 B1 N5 C9 -82.5(2) . . . . ? K1 B1 N5 C9 143.5(2) . . . . ? N1 B1 N5 N6 -155.19(15) . . . . ? N3 B1 N5 N6 87.0(2) . . . . ? K1 B1 N5 N6 -46.98(13) . . . . ? N1 B1 N5 K1 -108.21(13) . . . . ? N3 B1 N5 K1 133.94(14) . . . . ? N6 K1 N5 C9 88.2(2) . . . . ? S4 K1 N5 C9 83.72(18) . . . . ? S2 K1 N5 C9 -32.7(2) 2_766 . . . ? S1 K1 N5 C9 -76.37(17) . . . . ? S1 K1 N5 C9 -176.36(17) 2_766 . . . ? C1 K1 N5 C9 177.05(17) 2_766 . . . ? B1 K1 N5 C9 -140.5(2) . . . . ? K1 K1 N5 C9 -128.86(18) 2_766 . . . ? K2 K1 N5 C9 34.1(2) 2_655 . . . ? S4 K1 N5 N6 -4.43(12) . . . . ? S2 K1 N5 N6 -120.82(10) 2_766 . . . ? S1 K1 N5 N6 -164.52(11) . . . . ? S1 K1 N5 N6 95.49(11) 2_766 . . . ? C1 K1 N5 N6 88.90(12) 2_766 . . . ? B1 K1 N5 N6 131.38(16) . . . . ? K1 K1 N5 N6 142.98(11) 2_766 . . . ? K2 K1 N5 N6 -54.06(13) 2_655 . . . ? N6 K1 N5 B1 -131.38(16) . . . . ? S4 K1 N5 B1 -135.81(10) . . . . ? S2 K1 N5 B1 107.80(10) 2_766 . . . ? S1 K1 N5 B1 64.09(10) . . . . ? S1 K1 N5 B1 -35.89(10) 2_766 . . . ? C1 K1 N5 B1 -42.49(12) 2_766 . . . ? K1 K1 N5 B1 11.60(10) 2_766 . . . ? K2 K1 N5 B1 174.56(9) 2_655 . . . ? C10 C11 N6 N5 0.5(2) . . . . ? C10 C11 N6 K1 112.29(18) . . . . ? C9 N5 N6 C11 -0.3(2) . . . . ? B1 N5 N6 C11 -171.62(16) . . . . ? K1 N5 N6 C11 129.04(16) . . . . ? C9 N5 N6 K1 -129.37(14) . . . . ? B1 N5 N6 K1 59.34(16) . . . . ? S4 K1 N6 C11 61.05(16) . . . . ? S2 K1 N6 C11 -28.4(2) 2_766 . . . ? S1 K1 N6 C11 -100.98(16) . . . . ? S1 K1 N6 C11 154.50(16) 2_766 . . . ? N5 K1 N6 C11 -115.2(2) . . . . ? C1 K1 N6 C11 134.09(16) 2_766 . . . ? B1 K1 N6 C11 -142.67(19) . . . . ? K1 K1 N6 C11 -152.62(16) 2_766 . . . ? K2 K1 N6 C11 29.59(18) 2_655 . . . ? S4 K1 N6 N5 176.21(10) . . . . ? S2 K1 N6 N5 86.77(12) 2_766 . . . ? S1 K1 N6 N5 14.18(10) . . . . ? S1 K1 N6 N5 -90.34(11) 2_766 . . . ? C1 K1 N6 N5 -110.75(11) 2_766 . . . ? B1 K1 N6 N5 -27.51(10) . . . . ? K1 K1 N6 N5 -37.46(11) 2_766 . . . ? K2 K1 N6 N5 144.75(9) 2_655 . . . ? N8 C12 N7 C13 0.7(2) . . . . ? S3 C12 N7 C13 -178.41(15) . . . . ? K2 C12 N7 C13 -114.24(14) 2_655 . . . ? N8 C12 N7 B2 179.66(16) . . . . ? S3 C12 N7 B2 0.6(3) . . . . ? K2 C12 N7 B2 64.77(17) 2_655 . . . ? C14 C13 N7 C12 0.0(2) . . . . ? C14 C13 N7 B2 -179.00(18) . . . . ? N11 B2 N7 C12 73.4(2) . . . . ? N9 B2 N7 C12 -168.43(17) . . . . ? K2 B2 N7 C12 -1.0(2) . . . . ? N11 B2 N7 C13 -107.8(2) . . . . ? N9 B2 N7 C13 10.4(3) . . . . ? K2 B2 N7 C13 177.81(15) . . . . ? N7 C12 N8 C14 -1.0(2) . . . . ? S3 C12 N8 C14 178.05(16) . . . . ? K2 C12 N8 C14 90.76(17) 2_655 . . . ? N7 C12 N8 C15 -176.73(19) . . . . ? S3 C12 N8 C15 2.4(3) . . . . ? K2 C12 N8 C15 -84.9(2) 2_655 . . . ? C13 C14 N8 C12 1.0(2) . . . . ? C13 C14 N8 C15 176.7(2) . . . . ? N10 C16 N9 C17 0.3(2) . . . . ? S4 C16 N9 C17 -179.57(15) . . . . ? N10 C16 N9 B2 175.45(17) . . . . ? S4 C16 N9 B2 -4.4(3) . . . . ? C18 C17 N9 C16 -0.1(2) . . . . ? C18 C17 N9 B2 -175.23(18) . . . . ? N11 B2 N9 C16 -158.09(17) . . . . ? N7 B2 N9 C16 83.2(2) . . . . ? K2 B2 N9 C16 -80.6(2) . . . . ? N11 B2 N9 C17 16.2(3) . . . . ? N7 B2 N9 C17 -102.5(2) . . . . ? K2 B2 N9 C17 93.7(2) . . . . ? N9 C16 N10 C18 -0.4(2) . . . . ? S4 C16 N10 C18 179.49(15) . . . . ? N9 C16 N10 C19 176.61(18) . . . . ? S4 C16 N10 C19 -3.5(3) . . . . ? C17 C18 N10 C16 0.3(2) . . . . ? C17 C18 N10 C19 -176.65(19) . . . . ? C21 C20 N11 N12 -0.3(3) . . . . ? C21 C20 N11 B2 173.50(19) . . . . ? C21 C20 N11 K2 -71.7(2) . . . . ? N9 B2 N11 C20 -97.9(2) . . . . ? N7 B2 N11 C20 20.8(3) . . . . ? K2 B2 N11 C20 130.4(2) . . . . ? N9 B2 N11 N12 75.4(2) . . . . ? N7 B2 N11 N12 -165.90(15) . . . . ? K2 B2 N11 N12 -56.29(13) . . . . ? N9 B2 N11 K2 131.71(14) . . . . ? N7 B2 N11 K2 -109.61(13) . . . . ? N12 K2 N11 C20 98.19(19) . . . . ? S2 K2 N11 C20 86.56(16) 1_444 . . . ? S4 K2 N11 C20 -30.95(17) 2_655 . . . ? S3 K2 N11 C20 -70.53(15) . . . . ? S3 K2 N11 C20 -169.65(15) 2_655 . . . ? C12 K2 N11 C20 -175.40(15) 2_655 . . . ? B2 K2 N11 C20 -136.0(2) . . . . ? K2 K2 N11 C20 -123.11(16) 2_655 . . . ? K1 K2 N11 C20 32.95(19) 2_655 . . . ? S2 K2 N11 N12 -11.63(11) 1_444 . . . ? S4 K2 N11 N12 -129.14(10) 2_655 . . . ? S3 K2 N11 N12 -168.72(11) . . . . ? S3 K2 N11 N12 92.16(10) 2_655 . . . ? C12 K2 N11 N12 86.41(11) 2_655 . . . ? B2 K2 N11 N12 125.81(15) . . . . ? K2 K2 N11 N12 138.70(10) 2_655 . . . ? K1 K2 N11 N12 -65.24(12) 2_655 . . . ? N12 K2 N11 B2 -125.81(15) . . . . ? S2 K2 N11 B2 -137.43(9) 1_444 . . . ? S4 K2 N11 B2 105.05(10) 2_655 . . . ? S3 K2 N11 B2 65.48(10) . . . . ? S3 K2 N11 B2 -33.65(10) 2_655 . . . ? C12 K2 N11 B2 -39.39(12) 2_655 . . . ? K2 K2 N11 B2 12.89(10) 2_655 . . . ? K1 K2 N11 B2 168.95(9) 2_655 . . . ? C21 C22 N12 N11 -0.4(2) . . . . ? C21 C22 N12 K2 98.84(19) . . . . ? C20 N11 N12 C22 0.4(2) . . . . ? B2 N11 N12 C22 -174.20(16) . . . . ? K2 N11 N12 C22 118.40(15) . . . . ? C20 N11 N12 K2 -118.01(14) . . . . ? B2 N11 N12 K2 67.40(15) . . . . ? S2 K2 N12 C22 62.44(15) 1_444 . . . ? S4 K2 N12 C22 -30.22(18) 2_655 . . . ? N11 K2 N12 C22 -107.88(19) . . . . ? S3 K2 N12 C22 -97.49(15) . . . . ? S3 K2 N12 C22 158.85(14) 2_655 . . . ? C12 K2 N12 C22 138.93(14) 2_655 . . . ? B2 K2 N12 C22 -138.34(17) . . . . ? K2 K2 N12 C22 -149.66(14) 2_655 . . . ? K1 K2 N12 C22 31.33(17) 2_655 . . . ? S2 K2 N12 N11 170.32(9) 1_444 . . . ? S4 K2 N12 N11 77.66(12) 2_655 . . . ? S3 K2 N12 N11 10.39(10) . . . . ? S3 K2 N12 N11 -93.27(10) 2_655 . . . ? C12 K2 N12 N11 -113.19(10) 2_655 . . . ? B2 K2 N12 N11 -30.46(9) . . . . ? K2 K2 N12 N11 -41.78(10) 2_655 . . . ? K1 K2 N12 N11 139.21(9) 2_655 . . . ? N1 C1 S1 K1 -0.8(2) . . . . ? N2 C1 S1 K1 -179.63(14) . . . . ? K1 C1 S1 K1 -68.46(4) 2_766 . . . ? N1 C1 S1 K1 67.64(17) . . . 2_766 ? N2 C1 S1 K1 -111.17(17) . . . 2_766 ? N6 K1 S1 C1 -33.59(8) . . . . ? S4 K1 S1 C1 -148.41(9) . . . . ? S2 K1 S1 C1 -178.32(8) 2_766 . . . ? S1 K1 S1 C1 70.89(8) 2_766 . . . ? N5 K1 S1 C1 -27.40(8) . . . . ? C1 K1 S1 C1 99.06(8) 2_766 . . . ? B1 K1 S1 C1 0.11(8) . . . . ? K1 K1 S1 C1 70.89(8) 2_766 . . . ? K2 K1 S1 C1 -170.43(7) 2_655 . . . ? N6 K1 S1 K1 -104.48(4) . . . 2_766 ? S4 K1 S1 K1 140.70(6) . . . 2_766 ? S2 K1 S1 K1 110.789(17) 2_766 . . 2_766 ? S1 K1 S1 K1 0.0 2_766 . . 2_766 ? N5 K1 S1 K1 -98.30(3) . . . 2_766 ? C1 K1 S1 K1 28.16(4) 2_766 . . 2_766 ? B1 K1 S1 K1 -70.78(4) . . . 2_766 ? K2 K1 S1 K1 118.68(2) 2_655 . . 2_766 ? N4 C5 S2 K2 78.48(17) . . . 1_666 ? N3 C5 S2 K2 -101.27(18) . . . 1_666 ? N4 C5 S2 K1 -178.23(14) . . . 2_766 ? N3 C5 S2 K1 2.0(2) . . . 2_766 ? N7 C12 S3 K2 0.2(2) . . . . ? N8 C12 S3 K2 -178.70(15) . . . . ? K2 C12 S3 K2 -68.82(4) 2_655 . . . ? N7 C12 S3 K2 69.03(17) . . . 2_655 ? N8 C12 S3 K2 -109.88(17) . . . 2_655 ? N12 K2 S3 C12 -33.73(8) . . . . ? S2 K2 S3 C12 -154.60(8) 1_444 . . . ? S4 K2 S3 C12 179.67(7) 2_655 . . . ? N11 K2 S3 C12 -28.95(8) . . . . ? S3 K2 S3 C12 68.86(7) 2_655 . . . ? C12 K2 S3 C12 97.03(8) 2_655 . . . ? B2 K2 S3 C12 -0.44(8) . . . . ? K2 K2 S3 C12 68.86(7) 2_655 . . . ? K1 K2 S3 C12 -173.49(7) 2_655 . . . ? N12 K2 S3 K2 -102.59(4) . . . 2_655 ? S2 K2 S3 K2 136.55(5) 1_444 . . 2_655 ? S4 K2 S3 K2 110.810(17) 2_655 . . 2_655 ? N11 K2 S3 K2 -97.81(3) . . . 2_655 ? S3 K2 S3 K2 0.0 2_655 . . 2_655 ? C12 K2 S3 K2 28.17(4) 2_655 . . 2_655 ? B2 K2 S3 K2 -69.30(4) . . . 2_655 ? K1 K2 S3 K2 117.654(18) 2_655 . . 2_655 ? N10 C16 S4 K1 80.28(17) . . . . ? N9 C16 S4 K1 -99.88(18) . . . . ? N10 C16 S4 K2 -176.60(14) . . . 2_655 ? N9 C16 S4 K2 3.2(2) . . . 2_655 ? N6 K1 S4 C16 -23.00(7) . . . . ? S2 K1 S4 C16 120.09(7) 2_766 . . . ? S1 K1 S4 C16 90.44(9) . . . . ? S1 K1 S4 C16 -127.47(7) 2_766 . . . ? N5 K1 S4 C16 -21.20(8) . . . . ? C1 K1 S4 C16 -149.49(7) 2_766 . . . ? B1 K1 S4 C16 -48.16(9) . . . . ? K1 K1 S4 C16 -142.90(7) 2_766 . . . ? K2 K1 S4 C16 119.49(7) 2_655 . . . ? N6 K1 S4 K2 -142.50(4) . . . 2_655 ? S2 K1 S4 K2 0.599(15) 2_766 . . 2_655 ? S1 K1 S4 K2 -29.06(6) . . . 2_655 ? S1 K1 S4 K2 113.039(17) 2_766 . . 2_655 ? N5 K1 S4 K2 -140.69(4) . . . 2_655 ? C1 K1 S4 K2 91.02(4) 2_766 . . 2_655 ? B1 K1 S4 K2 -167.65(6) . . . 2_655 ? K1 K1 S4 K2 97.61(3) 2_766 . . 2_655 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.722 _refine_diff_density_min -1.229 _refine_diff_density_rms 0.293 data_KTpHmt _database_code_depnum_ccdc_archive 'CCDC 803999' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H16 B K N8 S' _chemical_formula_sum 'C13 H16 B K N8 S' _chemical_formula_weight 366.31 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.7702(4) _cell_length_b 11.5282(3) _cell_length_c 18.6564(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3606.85(14) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 33932 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.423 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.845838 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 31528 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4127 _reflns_number_gt 3543 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0239P)^2^+4.4838P] 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 4127 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group K1 K 0.01856(3) 0.51686(3) 0.10985(2) 0.02415(11) Uani 1 1 d . . . S1 S 0.11454(3) 0.50584(4) 0.26062(3) 0.02532(12) Uani 1 1 d . . . B1 B -0.08031(13) 0.79408(18) 0.00293(11) 0.0224(4) Uani 1 1 d . . . H1B H -0.1118 0.8647 0.0160 0.027 Uiso 1 1 calc R . . N1 N -0.00990(9) 0.78091(12) 0.05639(8) 0.0195(3) Uani 1 1 d . . . N2 N -0.02389(10) 0.77669(14) 0.12831(8) 0.0238(3) Uani 1 1 d . . . N3 N -0.13466(9) 0.68671(13) 0.00858(9) 0.0231(3) Uani 1 1 d . . . N4 N -0.10630(10) 0.57606(14) 0.01391(9) 0.0265(4) Uani 1 1 d . . . N5 N -0.04376(10) 0.81156(13) -0.07157(8) 0.0239(3) Uani 1 1 d . . . N6 N -0.01086(12) 0.72299(15) -0.10993(10) 0.0348(4) Uani 1 1 d . . . N7 N 0.17352(10) 0.71560(14) 0.30266(9) 0.0258(4) Uani 1 1 d . . . H7N H 0.1354 0.7296 0.3339 0.031 Uiso 1 1 calc R . . N8 N 0.24634(10) 0.63238(15) 0.22259(9) 0.0276(4) Uani 1 1 d . . . C1 C 0.06930(11) 0.78411(16) 0.04352(11) 0.0236(4) Uani 1 1 d . . . H1 H 0.0945 0.7988 -0.0042 0.028 Uiso 1 1 calc R . . C2 C 0.10911(12) 0.78128(17) 0.10834(11) 0.0268(4) Uani 1 1 d . . . H2 H 0.1668 0.7982 0.1170 0.032 Uiso 1 1 calc R . . C3 C 0.04818(12) 0.77683(17) 0.15929(11) 0.0269(4) Uani 1 1 d . . . H3 H 0.0565 0.7988 0.2106 0.032 Uiso 1 1 calc R . . C4 C -0.21486(12) 0.68624(19) 0.01333(13) 0.0342(5) Uani 1 1 d . . . H4 H -0.2482 0.7528 0.0111 0.041 Uiso 1 1 calc R . . C5 C -0.24077(14) 0.5739(2) 0.02193(14) 0.0410(6) Uani 1 1 d . . . H5 H -0.2940 0.5467 0.0265 0.049 Uiso 1 1 calc R . . C6 C -0.17049(13) 0.50927(18) 0.02230(12) 0.0322(5) Uani 1 1 d . . . H6 H -0.1686 0.4274 0.0279 0.039 Uiso 1 1 calc R . . C7 C -0.02040(14) 0.91490(17) -0.09934(11) 0.0309(5) Uani 1 1 d . . . H7 H -0.0348 0.9891 -0.0814 0.037 Uiso 1 1 calc R . . C8 C 0.02712(18) 0.8946(2) -0.15708(13) 0.0460(6) Uani 1 1 d . . . H8 H 0.0521 0.9500 -0.1874 0.055 Uiso 1 1 calc R . . C9 C 0.03085(18) 0.7737(2) -0.16155(14) 0.0484(7) Uani 1 1 d . . . H9 H 0.0598 0.7328 -0.1973 0.058 Uiso 1 1 calc R . . C10 C 0.17908(11) 0.61872(17) 0.26234(10) 0.0233(4) Uani 1 1 d . . . C11 C 0.23616(13) 0.78957(19) 0.28802(12) 0.0332(5) Uani 1 1 d . . . H11 H 0.2455 0.8632 0.3093 0.040 Uiso 1 1 calc R . . C12 C 0.28135(13) 0.7380(2) 0.23806(12) 0.0340(5) Uani 1 1 d . . . H12 H 0.3286 0.7684 0.2172 0.041 Uiso 1 1 calc R . . C13 C 0.27497(14) 0.5506(2) 0.16893(13) 0.0407(6) Uani 1 1 d . . . H13A H 0.3160 0.5878 0.1394 0.061 Uiso 0.50 1 calc PR . . H13B H 0.2305 0.5263 0.1384 0.061 Uiso 0.50 1 calc PR . . H13C H 0.2978 0.4825 0.1929 0.061 Uiso 0.50 1 calc PR . . H13D H 0.2468 0.4766 0.1744 0.061 Uiso 0.50 1 calc PR . . H13E H 0.3323 0.5382 0.1754 0.061 Uiso 0.50 1 calc PR . . H13F H 0.2650 0.5819 0.1209 0.061 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.0268(2) 0.0179(2) 0.0277(2) -0.00272(15) 0.00002(16) 0.00231(16) S1 0.0234(2) 0.0215(2) 0.0310(3) 0.00022(18) 0.00315(19) -0.00151(19) B1 0.0228(10) 0.0157(9) 0.0288(11) -0.0035(8) -0.0031(8) 0.0042(8) N1 0.0218(8) 0.0140(7) 0.0226(7) -0.0017(6) 0.0007(6) 0.0000(6) N2 0.0290(9) 0.0192(8) 0.0231(8) 0.0008(6) 0.0018(7) -0.0009(7) N3 0.0208(8) 0.0196(8) 0.0288(8) -0.0037(6) -0.0028(6) 0.0031(6) N4 0.0234(8) 0.0182(8) 0.0380(9) -0.0020(7) 0.0011(7) 0.0022(6) N5 0.0308(9) 0.0159(7) 0.0251(8) -0.0022(6) -0.0044(7) 0.0023(6) N6 0.0544(12) 0.0189(8) 0.0312(9) -0.0032(7) 0.0097(8) 0.0018(8) N7 0.0245(8) 0.0259(8) 0.0270(8) -0.0007(7) 0.0009(7) -0.0037(7) N8 0.0211(8) 0.0293(9) 0.0325(9) 0.0034(7) 0.0040(7) 0.0003(7) C1 0.0223(9) 0.0180(9) 0.0305(10) 0.0007(7) 0.0000(8) 0.0004(7) C2 0.0249(10) 0.0211(9) 0.0344(11) 0.0007(8) -0.0059(8) -0.0012(8) C3 0.0343(11) 0.0212(9) 0.0252(9) -0.0007(7) -0.0053(8) 0.0005(8) C4 0.0186(10) 0.0300(11) 0.0538(13) -0.0071(10) -0.0045(9) 0.0031(8) C5 0.0238(11) 0.0361(12) 0.0632(16) -0.0073(11) -0.0025(10) -0.0070(9) C6 0.0308(11) 0.0247(10) 0.0412(12) -0.0024(9) -0.0008(9) -0.0058(9) C7 0.0440(13) 0.0168(9) 0.0320(10) 0.0012(8) -0.0044(9) 0.0000(9) C8 0.0728(19) 0.0276(11) 0.0376(12) 0.0063(9) 0.0131(12) -0.0064(12) C9 0.0776(19) 0.0282(12) 0.0394(13) -0.0025(10) 0.0239(13) 0.0002(12) C10 0.0212(9) 0.0234(9) 0.0253(9) 0.0038(7) -0.0007(7) 0.0018(7) C11 0.0308(11) 0.0304(11) 0.0385(11) 0.0022(9) -0.0031(9) -0.0116(9) C12 0.0239(10) 0.0372(12) 0.0411(12) 0.0074(9) 0.0006(9) -0.0080(9) C13 0.0361(12) 0.0400(13) 0.0460(13) -0.0012(10) 0.0181(10) 0.0038(10) _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 K1 N6 2.7680(18) 5_565 ? K1 N4 2.8379(17) . ? K1 N4 2.9400(17) 5_565 ? K1 N2 3.0980(16) . ? K1 C3 3.175(2) . ? K1 N1 3.2385(15) . ? K1 S1 3.2434(7) . ? K1 S1 3.2922(6) 3 ? K1 C2 3.406(2) . ? K1 C1 3.4274(19) . ? S1 C10 1.693(2) . ? S1 K1 3.2922(6) 3 ? B1 N5 1.532(3) . ? B1 N3 1.541(3) . ? B1 N1 1.553(3) . ? B1 H1B 1.0000 . ? N1 C1 1.350(2) . ? N1 N2 1.363(2) . ? N2 C3 1.340(3) . ? N3 C4 1.348(3) . ? N3 N4 1.365(2) . ? N4 C6 1.333(3) . ? N4 K1 2.9400(17) 5_565 ? N5 C7 1.357(3) . ? N5 N6 1.363(2) . ? N6 C9 1.326(3) . ? N6 K1 2.7680(18) 5_565 ? N7 C10 1.350(2) . ? N7 C11 1.380(3) . ? N7 H7N 0.8800 . ? N8 C10 1.359(2) . ? N8 C12 1.383(3) . ? N8 C13 1.457(3) . ? C1 C2 1.382(3) . ? C1 H1 1.0000 . ? C2 C3 1.396(3) . ? C2 H2 1.0000 . ? C3 H3 1.0000 . ? C4 C5 1.375(3) . ? C4 H4 0.9500 . ? C5 C6 1.395(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.360(3) . ? C7 H7 0.9500 . ? C8 C9 1.398(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C11 C12 1.340(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 H13D 0.9800 . ? C13 H13E 0.9800 . ? C13 H13F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 K1 N4 101.89(6) 5_565 . ? N6 K1 N4 70.11(5) 5_565 5_565 ? N4 K1 N4 87.80(5) . 5_565 ? N6 K1 N2 162.75(5) 5_565 . ? N4 K1 N2 70.61(5) . . ? N4 K1 N2 123.69(5) 5_565 . ? N6 K1 C3 161.82(6) 5_565 . ? N4 K1 C3 94.11(5) . . ? N4 K1 C3 119.59(5) 5_565 . ? N2 K1 C3 24.63(5) . . ? N6 K1 N1 158.78(5) 5_565 . ? N4 K1 N1 58.06(4) . . ? N4 K1 N1 100.04(4) 5_565 . ? N2 K1 N1 24.71(4) . . ? C3 K1 N1 39.22(4) . . ? N6 K1 S1 89.06(4) 5_565 . ? N4 K1 S1 157.30(4) . . ? N4 K1 S1 114.74(4) 5_565 . ? N2 K1 S1 93.18(3) . . ? C3 K1 S1 72.98(4) . . ? N1 K1 S1 112.15(3) . . ? N6 K1 S1 85.95(4) 5_565 3 ? N4 K1 S1 88.39(4) . 3 ? N4 K1 S1 154.39(4) 5_565 3 ? N2 K1 S1 78.46(3) . 3 ? C3 K1 S1 85.94(4) . 3 ? N1 K1 S1 99.35(3) . 3 ? S1 K1 S1 72.443(16) . 3 ? N6 K1 C2 156.19(6) 5_565 . ? N4 K1 C2 96.23(5) . . ? N4 K1 C2 95.54(5) 5_565 . ? N2 K1 C2 40.36(5) . . ? C3 K1 C2 24.18(5) . . ? N1 K1 C2 38.91(4) . . ? S1 K1 C2 79.68(4) . . ? S1 K1 C2 110.05(4) 3 . ? N6 K1 C1 155.46(5) 5_565 . ? N4 K1 C1 74.89(5) . . ? N4 K1 C1 85.40(5) 5_565 . ? N2 K1 C1 39.47(4) . . ? C3 K1 C1 38.51(5) . . ? N1 K1 C1 23.15(4) . . ? S1 K1 C1 103.01(4) . . ? S1 K1 C1 117.91(4) 3 . ? C2 K1 C1 23.33(5) . . ? N6 K1 K1 84.28(4) 5_565 5_565 ? N4 K1 K1 44.87(3) . 5_565 ? N4 K1 K1 42.93(3) 5_565 5_565 ? N2 K1 K1 99.52(3) . 5_565 ? C3 K1 K1 113.42(4) . 5_565 ? N1 K1 K1 76.27(3) . 5_565 ? S1 K1 K1 157.55(2) . 5_565 ? S1 K1 K1 128.139(19) 3 5_565 ? C2 K1 K1 98.17(4) . 5_565 ? C1 K1 K1 76.45(3) . 5_565 ? C10 S1 K1 107.67(7) . . ? C10 S1 K1 112.95(7) . 3 ? K1 S1 K1 107.374(16) . 3 ? N5 B1 N3 113.85(15) . . ? N5 B1 N1 106.93(15) . . ? N3 B1 N1 109.11(15) . . ? N5 B1 H1B 109.0 . . ? N3 B1 H1B 109.0 . . ? N1 B1 H1B 109.0 . . ? C1 N1 N2 110.21(15) . . ? C1 N1 B1 129.13(16) . . ? N2 N1 B1 120.31(15) . . ? C1 N1 K1 86.30(10) . . ? N2 N1 K1 71.86(9) . . ? B1 N1 K1 113.68(10) . . ? C3 N2 N1 105.62(16) . . ? C3 N2 K1 80.90(11) . . ? N1 N2 K1 83.42(9) . . ? C4 N3 N4 109.83(16) . . ? C4 N3 B1 126.73(16) . . ? N4 N3 B1 123.34(15) . . ? C6 N4 N3 105.49(16) . . ? C6 N4 K1 112.51(13) . . ? N3 N4 K1 121.86(11) . . ? C6 N4 K1 106.62(13) . 5_565 ? N3 N4 K1 117.24(12) . 5_565 ? K1 N4 K1 92.20(5) . 5_565 ? C7 N5 N6 109.90(17) . . ? C7 N5 B1 125.26(16) . . ? N6 N5 B1 122.64(15) . . ? C9 N6 N5 105.34(17) . . ? C9 N6 K1 117.73(14) . 5_565 ? N5 N6 K1 136.79(13) . 5_565 ? C10 N7 C11 110.38(17) . . ? C10 N7 H7N 124.8 . . ? C11 N7 H7N 124.8 . . ? C10 N8 C12 109.91(17) . . ? C10 N8 C13 124.99(18) . . ? C12 N8 C13 125.03(18) . . ? N1 C1 C2 108.60(17) . . ? N1 C1 K1 70.55(10) . . ? C2 C1 K1 77.45(11) . . ? N1 C1 H1 125.4 . . ? C2 C1 H1 125.4 . . ? K1 C1 H1 125.4 . . ? C1 C2 C3 104.06(17) . . ? C1 C2 K1 79.21(11) . . ? C3 C2 K1 68.61(11) . . ? C1 C2 H2 127.2 . . ? C3 C2 H2 127.2 . . ? K1 C2 H2 127.2 . . ? N2 C3 C2 111.51(17) . . ? N2 C3 K1 74.48(11) . . ? C2 C3 K1 87.22(12) . . ? N2 C3 H3 122.7 . . ? C2 C3 H3 122.7 . . ? K1 C3 H3 122.7 . . ? N3 C4 C5 109.06(19) . . ? N3 C4 H4 125.5 . . ? C5 C4 H4 125.5 . . ? C4 C5 C6 103.69(19) . . ? C4 C5 H5 128.2 . . ? C6 C5 H5 128.2 . . ? N4 C6 C5 111.92(19) . . ? N4 C6 H6 124.0 . . ? C5 C6 H6 124.0 . . ? N5 C7 C8 108.70(19) . . ? N5 C7 H7 125.7 . . ? C8 C7 H7 125.7 . . ? C7 C8 C9 104.2(2) . . ? C7 C8 H8 127.9 . . ? C9 C8 H8 127.9 . . ? N6 C9 C8 111.9(2) . . ? N6 C9 H9 124.1 . . ? C8 C9 H9 124.1 . . ? N7 C10 N8 105.41(17) . . ? N7 C10 S1 127.04(15) . . ? N8 C10 S1 127.54(15) . . ? C12 C11 N7 107.11(19) . . ? C12 C11 H11 126.4 . . ? N7 C11 H11 126.4 . . ? C11 C12 N8 107.19(18) . . ? C11 C12 H12 126.4 . . ? N8 C12 H12 126.4 . . ? N8 C13 H13A 109.5 . . ? N8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N8 C13 H13D 109.5 . . ? H13A C13 H13D 141.1 . . ? H13B C13 H13D 56.3 . . ? H13C C13 H13D 56.3 . . ? N8 C13 H13E 109.5 . . ? H13A C13 H13E 56.3 . . ? H13B C13 H13E 141.1 . . ? H13C C13 H13E 56.3 . . ? H13D C13 H13E 109.5 . . ? N8 C13 H13F 109.5 . . ? H13A C13 H13F 56.3 . . ? H13B C13 H13F 56.3 . . ? H13C C13 H13F 141.1 . . ? H13D C13 H13F 109.5 . . ? H13E C13 H13F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N6 K1 S1 C10 147.41(8) 5_565 . . . ? N4 K1 S1 C10 -92.92(12) . . . . ? N4 K1 S1 C10 79.88(8) 5_565 . . . ? N2 K1 S1 C10 -49.71(8) . . . . ? C3 K1 S1 C10 -35.44(8) . . . . ? N1 K1 S1 C10 -33.38(8) . . . . ? S1 K1 S1 C10 -126.54(7) 3 . . . ? C2 K1 S1 C10 -11.50(8) . . . . ? C1 K1 S1 C10 -11.03(8) . . . . ? K1 K1 S1 C10 74.93(9) 5_565 . . . ? N6 K1 S1 K1 -90.68(4) 5_565 . . 3 ? N4 K1 S1 K1 28.98(10) . . . 3 ? N4 K1 S1 K1 -158.22(4) 5_565 . . 3 ? N2 K1 S1 K1 72.20(4) . . . 3 ? C3 K1 S1 K1 86.47(4) . . . 3 ? N1 K1 S1 K1 88.53(3) . . . 3 ? S1 K1 S1 K1 -4.63(2) 3 . . 3 ? C2 K1 S1 K1 110.40(4) . . . 3 ? C1 K1 S1 K1 110.88(4) . . . 3 ? K1 K1 S1 K1 -163.17(4) 5_565 . . 3 ? N5 B1 N1 C1 0.4(2) . . . . ? N3 B1 N1 C1 123.96(19) . . . . ? N5 B1 N1 N2 172.88(14) . . . . ? N3 B1 N1 N2 -63.6(2) . . . . ? N5 B1 N1 K1 -105.02(13) . . . . ? N3 B1 N1 K1 18.54(17) . . . . ? N6 K1 N1 C1 -111.68(16) 5_565 . . . ? N4 K1 N1 C1 -132.58(12) . . . . ? N4 K1 N1 C1 -51.57(11) 5_565 . . . ? N2 K1 N1 C1 112.67(15) . . . . ? C3 K1 N1 C1 73.61(12) . . . . ? S1 K1 N1 C1 70.50(11) . . . . ? S1 K1 N1 C1 145.25(10) 3 . . . ? C2 K1 N1 C1 34.80(11) . . . . ? K1 K1 N1 C1 -87.59(10) 5_565 . . . ? N6 K1 N1 N2 135.65(15) 5_565 . . . ? N4 K1 N1 N2 114.75(11) . . . . ? N4 K1 N1 N2 -164.24(10) 5_565 . . . ? C3 K1 N1 N2 -39.06(10) . . . . ? S1 K1 N1 N2 -42.17(10) . . . . ? S1 K1 N1 N2 32.57(10) 3 . . . ? C2 K1 N1 N2 -77.88(11) . . . . ? C1 K1 N1 N2 -112.67(15) . . . . ? K1 K1 N1 N2 159.74(10) 5_565 . . . ? N6 K1 N1 B1 19.8(2) 5_565 . . . ? N4 K1 N1 B1 -1.11(11) . . . . ? N4 K1 N1 B1 79.90(12) 5_565 . . . ? N2 K1 N1 B1 -115.86(16) . . . . ? C3 K1 N1 B1 -154.92(15) . . . . ? S1 K1 N1 B1 -158.04(11) . . . . ? S1 K1 N1 B1 -83.29(11) 3 . . . ? C2 K1 N1 B1 166.26(15) . . . . ? C1 K1 N1 B1 131.46(17) . . . . ? K1 K1 N1 B1 43.87(11) 5_565 . . . ? C1 N1 N2 C3 -0.3(2) . . . . ? B1 N1 N2 C3 -174.05(15) . . . . ? K1 N1 N2 C3 78.60(12) . . . . ? C1 N1 N2 K1 -78.88(13) . . . . ? B1 N1 N2 K1 107.34(14) . . . . ? N6 K1 N2 C3 131.54(19) 5_565 . . . ? N4 K1 N2 C3 -161.82(12) . . . . ? N4 K1 N2 C3 -88.28(12) 5_565 . . . ? N1 K1 N2 C3 -107.03(15) . . . . ? S1 K1 N2 C3 34.45(11) . . . . ? S1 K1 N2 C3 105.80(11) 3 . . . ? C2 K1 N2 C3 -35.53(11) . . . . ? C1 K1 N2 C3 -72.24(12) . . . . ? K1 K1 N2 C3 -126.98(11) 5_565 . . . ? N6 K1 N2 N1 -121.43(18) 5_565 . . . ? N4 K1 N2 N1 -54.79(10) . . . . ? N4 K1 N2 N1 18.75(12) 5_565 . . . ? C3 K1 N2 N1 107.03(15) . . . . ? S1 K1 N2 N1 141.48(9) . . . . ? S1 K1 N2 N1 -147.17(10) 3 . . . ? C2 K1 N2 N1 71.50(11) . . . . ? C1 K1 N2 N1 34.79(9) . . . . ? K1 K1 N2 N1 -19.95(10) 5_565 . . . ? N5 B1 N3 C4 -107.2(2) . . . . ? N1 B1 N3 C4 133.4(2) . . . . ? N5 B1 N3 N4 76.9(2) . . . . ? N1 B1 N3 N4 -42.4(2) . . . . ? C4 N3 N4 C6 -0.3(2) . . . . ? B1 N3 N4 C6 176.10(17) . . . . ? C4 N3 N4 K1 -130.12(15) . . . . ? B1 N3 N4 K1 46.3(2) . . . . ? C4 N3 N4 K1 118.12(15) . . . 5_565 ? B1 N3 N4 K1 -65.45(19) . . . 5_565 ? N6 K1 N4 C6 39.86(15) 5_565 . . . ? N4 K1 N4 C6 109.01(15) 5_565 . . . ? N2 K1 N4 C6 -123.98(14) . . . . ? C3 K1 N4 C6 -131.47(14) . . . . ? N1 K1 N4 C6 -147.72(15) . . . . ? S1 K1 N4 C6 -77.53(17) . . . . ? S1 K1 N4 C6 -45.66(14) 3 . . . ? C2 K1 N4 C6 -155.66(14) . . . . ? C1 K1 N4 C6 -165.17(15) . . . . ? K1 K1 N4 C6 109.01(15) 5_565 . . . ? N6 K1 N4 N3 166.58(13) 5_565 . . . ? N4 K1 N4 N3 -124.27(15) 5_565 . . . ? N2 K1 N4 N3 2.74(13) . . . . ? C3 K1 N4 N3 -4.75(14) . . . . ? N1 K1 N4 N3 -21.00(12) . . . . ? S1 K1 N4 N3 49.2(2) . . . . ? S1 K1 N4 N3 81.06(13) 3 . . . ? C2 K1 N4 N3 -28.94(14) . . . . ? C1 K1 N4 N3 -38.45(13) . . . . ? K1 K1 N4 N3 -124.27(15) 5_565 . . . ? N6 K1 N4 K1 -69.15(5) 5_565 . . 5_565 ? N4 K1 N4 K1 0.0 5_565 . . 5_565 ? N2 K1 N4 K1 127.01(5) . . . 5_565 ? C3 K1 N4 K1 119.52(5) . . . 5_565 ? N1 K1 N4 K1 103.27(5) . . . 5_565 ? S1 K1 N4 K1 173.46(7) . . . 5_565 ? S1 K1 N4 K1 -154.67(4) 3 . . 5_565 ? C2 K1 N4 K1 95.33(5) . . . 5_565 ? C1 K1 N4 K1 85.82(5) . . . 5_565 ? N3 B1 N5 C7 153.58(18) . . . . ? N1 B1 N5 C7 -85.8(2) . . . . ? N3 B1 N5 N6 -45.0(2) . . . . ? N1 B1 N5 N6 75.6(2) . . . . ? C7 N5 N6 C9 -1.3(3) . . . . ? B1 N5 N6 C9 -165.2(2) . . . . ? C7 N5 N6 K1 -176.65(16) . . . 5_565 ? B1 N5 N6 K1 19.4(3) . . . 5_565 ? N2 N1 C1 C2 0.4(2) . . . . ? B1 N1 C1 C2 173.43(16) . . . . ? K1 N1 C1 C2 -68.78(14) . . . . ? N2 N1 C1 K1 69.13(11) . . . . ? B1 N1 C1 K1 -117.79(17) . . . . ? N6 K1 C1 N1 125.90(15) 5_565 . . . ? N4 K1 C1 N1 40.34(10) . . . . ? N4 K1 C1 N1 129.30(11) 5_565 . . . ? N2 K1 C1 N1 -37.36(10) . . . . ? C3 K1 C1 N1 -76.95(12) . . . . ? S1 K1 C1 N1 -116.35(10) . . . . ? S1 K1 C1 N1 -39.53(11) 3 . . . ? C2 K1 C1 N1 -115.16(17) . . . . ? K1 K1 C1 N1 86.71(10) 5_565 . . . ? N6 K1 C1 C2 -118.94(16) 5_565 . . . ? N4 K1 C1 C2 155.50(13) . . . . ? N4 K1 C1 C2 -115.54(12) 5_565 . . . ? N2 K1 C1 C2 77.80(13) . . . . ? C3 K1 C1 C2 38.21(12) . . . . ? N1 K1 C1 C2 115.16(17) . . . . ? S1 K1 C1 C2 -1.19(12) . . . . ? S1 K1 C1 C2 75.63(12) 3 . . . ? K1 K1 C1 C2 -158.13(12) 5_565 . . . ? N1 C1 C2 C3 -0.3(2) . . . . ? K1 C1 C2 C3 -64.50(13) . . . . ? N1 C1 C2 K1 64.22(13) . . . . ? N6 K1 C2 C1 115.81(15) 5_565 . . . ? N4 K1 C2 C1 -23.75(12) . . . . ? N4 K1 C2 C1 64.64(12) 5_565 . . . ? N2 K1 C2 C1 -73.64(12) . . . . ? C3 K1 C2 C1 -109.89(17) . . . . ? N1 K1 C2 C1 -34.50(10) . . . . ? S1 K1 C2 C1 178.82(12) . . . . ? S1 K1 C2 C1 -114.31(11) 3 . . . ? K1 K1 C2 C1 21.46(12) 5_565 . . . ? N6 K1 C2 C3 -134.30(15) 5_565 . . . ? N4 K1 C2 C3 86.14(12) . . . . ? N4 K1 C2 C3 174.53(12) 5_565 . . . ? N2 K1 C2 C3 36.25(11) . . . . ? N1 K1 C2 C3 75.39(12) . . . . ? S1 K1 C2 C3 -71.29(11) . . . . ? S1 K1 C2 C3 -4.42(12) 3 . . . ? C1 K1 C2 C3 109.89(17) . . . . ? K1 K1 C2 C3 131.35(11) 5_565 . . . ? N1 N2 C3 C2 0.1(2) . . . . ? K1 N2 C3 C2 80.58(15) . . . . ? N1 N2 C3 K1 -80.49(11) . . . . ? C1 C2 C3 N2 0.1(2) . . . . ? K1 C2 C3 N2 -72.11(14) . . . . ? C1 C2 C3 K1 72.22(13) . . . . ? N6 K1 C3 N2 -134.64(18) 5_565 . . . ? N4 K1 C3 N2 17.16(11) . . . . ? N4 K1 C3 N2 106.97(11) 5_565 . . . ? N1 K1 C3 N2 39.22(10) . . . . ? S1 K1 C3 N2 -143.80(12) . . . . ? S1 K1 C3 N2 -70.93(11) 3 . . . ? C2 K1 C3 N2 113.23(17) . . . . ? C1 K1 C3 N2 76.50(12) . . . . ? K1 K1 C3 N2 59.16(12) 5_565 . . . ? N6 K1 C3 C2 112.1(2) 5_565 . . . ? N4 K1 C3 C2 -96.07(12) . . . . ? N4 K1 C3 C2 -6.26(13) 5_565 . . . ? N2 K1 C3 C2 -113.23(17) . . . . ? N1 K1 C3 C2 -74.01(12) . . . . ? S1 K1 C3 C2 102.97(12) . . . . ? S1 K1 C3 C2 175.84(12) 3 . . . ? C1 K1 C3 C2 -36.73(11) . . . . ? K1 K1 C3 C2 -54.07(12) 5_565 . . . ? N4 N3 C4 C5 0.0(3) . . . . ? B1 N3 C4 C5 -176.29(19) . . . . ? N3 C4 C5 C6 0.3(3) . . . . ? N3 N4 C6 C5 0.6(2) . . . . ? K1 N4 C6 C5 135.61(17) . . . . ? K1 N4 C6 C5 -124.78(17) 5_565 . . . ? C4 C5 C6 N4 -0.6(3) . . . . ? N6 N5 C7 C8 1.0(3) . . . . ? B1 N5 C7 C8 164.4(2) . . . . ? N5 C7 C8 C9 -0.3(3) . . . . ? N5 N6 C9 C8 1.1(3) . . . . ? K1 N6 C9 C8 177.50(19) 5_565 . . . ? C7 C8 C9 N6 -0.5(3) . . . . ? C11 N7 C10 N8 0.5(2) . . . . ? C11 N7 C10 S1 -178.32(15) . . . . ? C12 N8 C10 N7 -0.6(2) . . . . ? C13 N8 C10 N7 -177.66(19) . . . . ? C12 N8 C10 S1 178.12(16) . . . . ? C13 N8 C10 S1 1.1(3) . . . . ? K1 S1 C10 N7 107.91(17) . . . . ? K1 S1 C10 N7 -10.47(19) 3 . . . ? K1 S1 C10 N8 -70.61(18) . . . . ? K1 S1 C10 N8 171.02(15) 3 . . . ? C10 N7 C11 C12 -0.1(2) . . . . ? N7 C11 C12 N8 -0.3(2) . . . . ? C10 N8 C12 C11 0.6(2) . . . . ? C13 N8 C12 C11 177.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.425 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.057 data_3 _database_code_depnum_ccdc_archive 'CCDC 804000' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H30 B Ir N6 S2, C1 H2 Cl2' _chemical_formula_sum 'C22 H32 B Cl2 Ir N6 S2' _chemical_formula_weight 718.57 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.2566(2) _cell_length_b 9.7542(2) _cell_length_c 17.7813(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.7010(10) _cell_angle_gamma 90.00 _cell_volume 2640.62(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 22326 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour 'Pale Brown' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 5.441 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5354 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_reflns_number 37344 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6051 _reflns_number_gt 5329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement ; DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) ; _computing_data_reduction ; DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0159P)^2^+3.7803P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6051 _refine_ls_number_parameters 324 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0495 _refine_ls_wR_factor_gt 0.0476 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.226977(7) 0.207108(11) 0.114124(6) 0.00849(4) Uani 1 1 d . . . H1 H 0.287(2) 0.205(3) 0.1847(17) 0.010 Uiso 1 1 d . . . S1 S 0.11690(5) 0.21613(8) 0.20403(4) 0.01392(16) Uani 1 1 d . . . S2 S 0.11182(5) 0.25421(8) 0.01398(4) 0.01378(15) Uani 1 1 d . . . N1 N 0.18345(15) 0.4719(3) 0.19606(13) 0.0106(5) Uani 1 1 d . . . N2 N 0.08516(16) 0.4558(3) 0.27998(13) 0.0132(5) Uani 1 1 d . . . N3 N 0.18633(15) 0.4969(2) 0.05588(13) 0.0096(5) Uani 1 1 d . . . N4 N 0.09186(15) 0.5157(3) -0.04204(13) 0.0123(5) Uani 1 1 d . . . N5 N 0.32693(15) 0.4965(2) 0.13643(13) 0.0098(5) Uani 1 1 d . . . N6 N 0.36159(15) 0.5625(3) 0.07639(13) 0.0111(5) Uani 1 1 d . . . B1 B 0.2356(2) 0.4268(4) 0.12595(18) 0.0093(6) Uani 1 1 d . . . C1 C 0.12859(18) 0.3852(3) 0.22839(15) 0.0104(6) Uani 1 1 d . . . C2 C 0.17478(19) 0.6006(3) 0.22847(16) 0.0154(6) Uani 1 1 d . . . H2 H 0.2058 0.6812 0.2162 0.018 Uiso 1 1 calc R . . C3 C 0.1143(2) 0.5905(3) 0.28053(17) 0.0161(7) Uani 1 1 d . . . H3 H 0.0953 0.6623 0.3117 0.019 Uiso 1 1 calc R . . C4 C 0.0193(2) 0.3986(4) 0.32697(18) 0.0225(7) Uani 1 1 d . . . H4A H -0.0167 0.3319 0.2977 0.034 Uiso 1 1 calc R . . H4B H -0.0182 0.4725 0.3440 0.034 Uiso 1 1 calc R . . H4C H 0.0486 0.3531 0.3708 0.034 Uiso 1 1 calc R . . C5 C 0.13093(18) 0.4265(3) 0.00820(16) 0.0101(6) Uani 1 1 d . . . C6 C 0.18065(19) 0.6348(3) 0.03609(17) 0.0144(6) Uani 1 1 d . . . H6 H 0.2120 0.7080 0.0607 0.017 Uiso 1 1 calc R . . C7 C 0.12274(19) 0.6463(3) -0.02432(17) 0.0151(6) Uani 1 1 d . . . H7 H 0.1062 0.7287 -0.0500 0.018 Uiso 1 1 calc R . . C8 C 0.0343(2) 0.4785(3) -0.10721(17) 0.0171(7) Uani 1 1 d . . . H8A H 0.0696 0.4443 -0.1473 0.026 Uiso 1 1 calc R . . H8B H 0.0010 0.5593 -0.1252 0.026 Uiso 1 1 calc R . . H8C H -0.0065 0.4069 -0.0930 0.026 Uiso 1 1 calc R . . C9 C 0.38628(19) 0.4988(3) 0.19766(16) 0.0138(6) Uani 1 1 d . . . C10 C 0.45936(19) 0.5699(3) 0.17694(17) 0.0151(6) Uani 1 1 d . . . H10 H 0.5113 0.5893 0.2074 0.018 Uiso 1 1 calc R . . C11 C 0.44067(18) 0.6073(3) 0.10155(17) 0.0129(6) Uani 1 1 d . . . C12 C 0.3715(2) 0.4312(4) 0.27091(17) 0.0198(7) Uani 1 1 d . . . H12A H 0.3249 0.4795 0.2956 0.030 Uiso 1 1 calc R . . H12B H 0.4258 0.4341 0.3034 0.030 Uiso 1 1 calc R . . H12C H 0.3541 0.3356 0.2619 0.030 Uiso 1 1 calc R . . C13 C 0.4966(2) 0.6867(3) 0.05019(19) 0.0198(7) Uani 1 1 d . . . H13A H 0.5270 0.6229 0.0182 0.030 Uiso 1 1 calc R . . H13B H 0.5400 0.7409 0.0805 0.030 Uiso 1 1 calc R . . H13C H 0.4593 0.7482 0.0184 0.030 Uiso 1 1 calc R . . C14 C 0.31002(19) 0.2119(3) 0.02027(16) 0.0131(6) Uani 1 1 d . . . H14 H 0.3171 0.3051 -0.0019 0.016 Uiso 1 1 calc R . . C15 C 0.36320(18) 0.1883(3) 0.08628(17) 0.0146(6) Uani 1 1 d . . . H15 H 0.4007 0.2683 0.1027 0.017 Uiso 1 1 calc R . . C16 C 0.4050(2) 0.0495(3) 0.10549(19) 0.0211(7) Uani 1 1 d . . . H16A H 0.4621 0.0650 0.1340 0.025 Uiso 1 1 calc R . . H16B H 0.4171 0.0023 0.0580 0.025 Uiso 1 1 calc R . . C17 C 0.3489(2) -0.0451(4) 0.1519(2) 0.0252(8) Uani 1 1 d . . . H17A H 0.3630 -0.1415 0.1401 0.030 Uiso 1 1 calc R . . H17B H 0.3651 -0.0301 0.2061 0.030 Uiso 1 1 calc R . . C18 C 0.2507(2) -0.0238(3) 0.13790(18) 0.0162(6) Uani 1 1 d . . . H18 H 0.2150 -0.0623 0.1781 0.019 Uiso 1 1 calc R . . C19 C 0.2066(2) -0.0153(3) 0.06836(18) 0.0157(6) Uani 1 1 d . . . H19 H 0.1444 -0.0483 0.0668 0.019 Uiso 1 1 calc R . . C20 C 0.2509(2) -0.0326(4) -0.00524(19) 0.0238(8) Uani 1 1 d . . . H20A H 0.2078 -0.0720 -0.0432 0.029 Uiso 1 1 calc R . . H20B H 0.2994 -0.0995 0.0029 0.029 Uiso 1 1 calc R . . C21 C 0.2883(2) 0.1004(3) -0.03755(17) 0.0184(7) Uani 1 1 d . . . H21A H 0.3423 0.0775 -0.0629 0.022 Uiso 1 1 calc R . . H21B H 0.2450 0.1371 -0.0763 0.022 Uiso 1 1 calc R . . Cl1 Cl 0.27122(6) 1.04492(12) 0.34546(5) 0.0382(2) Uani 1 1 d . . . C22A C 0.3432(2) 0.9267(4) 0.39308(19) 0.0261(8) Uani 0.30(5) 1 d PD A 1 H22A H 0.4019 0.9696 0.4011 0.031 Uiso 0.30(5) 1 calc PR A 1 H22B H 0.3215 0.9074 0.4433 0.031 Uiso 0.30(5) 1 calc PR A 1 Cl2A Cl 0.355(2) 0.7696(16) 0.3451(11) 0.045(4) Uani 0.30(5) 1 d PD A 1 C22B C 0.3432(2) 0.9267(4) 0.39308(19) 0.0261(8) Uani 0.70(5) 1 d PD A 2 H22C H 0.4046 0.9585 0.3908 0.031 Uiso 0.70(5) 1 calc PR A 2 H22D H 0.3299 0.9214 0.4467 0.031 Uiso 0.70(5) 1 calc PR A 2 Cl2B Cl 0.3320(9) 0.7639(6) 0.3519(4) 0.0543(17) Uani 0.70(5) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.00962(6) 0.00699(6) 0.00899(6) 0.00028(4) 0.00170(4) -0.00023(4) S1 0.0151(4) 0.0106(4) 0.0168(4) 0.0007(3) 0.0068(3) -0.0021(3) S2 0.0145(4) 0.0101(4) 0.0161(4) -0.0013(3) -0.0033(3) -0.0020(3) N1 0.0113(12) 0.0111(13) 0.0094(12) -0.0028(10) 0.0008(9) -0.0001(10) N2 0.0149(12) 0.0150(14) 0.0102(12) 0.0007(10) 0.0043(10) 0.0034(10) N3 0.0083(12) 0.0084(12) 0.0118(12) 0.0003(10) -0.0021(9) -0.0016(9) N4 0.0130(12) 0.0144(14) 0.0092(12) 0.0011(10) -0.0016(10) 0.0001(10) N5 0.0120(12) 0.0088(13) 0.0090(12) 0.0005(9) 0.0027(9) -0.0001(10) N6 0.0113(12) 0.0122(13) 0.0101(12) 0.0009(10) 0.0032(9) -0.0015(10) B1 0.0051(15) 0.0144(17) 0.0085(15) 0.0039(13) 0.0017(12) 0.0015(12) C1 0.0101(14) 0.0124(15) 0.0086(13) 0.0011(12) 0.0017(11) 0.0018(12) C2 0.0192(16) 0.0122(16) 0.0148(15) -0.0045(12) 0.0014(12) -0.0010(12) C3 0.0197(16) 0.0144(17) 0.0143(15) -0.0028(12) 0.0018(12) 0.0044(13) C4 0.0230(17) 0.026(2) 0.0201(17) 0.0045(15) 0.0132(14) 0.0039(14) C5 0.0091(14) 0.0106(15) 0.0109(14) 0.0008(11) 0.0019(11) 0.0008(11) C6 0.0130(14) 0.0110(16) 0.0192(15) 0.0019(13) 0.0010(12) -0.0012(12) C7 0.0168(15) 0.0113(16) 0.0174(15) 0.0038(12) 0.0025(12) 0.0018(12) C8 0.0157(15) 0.0222(18) 0.0128(15) 0.0011(13) -0.0039(12) 0.0006(13) C9 0.0147(15) 0.0149(16) 0.0114(14) -0.0013(12) -0.0019(12) 0.0002(12) C10 0.0096(14) 0.0174(17) 0.0179(15) -0.0017(13) -0.0019(12) -0.0029(12) C11 0.0112(14) 0.0075(15) 0.0201(15) -0.0021(12) 0.0016(12) -0.0016(11) C12 0.0196(16) 0.0246(19) 0.0146(15) 0.0047(14) -0.0042(13) -0.0067(14) C13 0.0162(16) 0.0206(18) 0.0232(17) 0.0005(14) 0.0072(13) -0.0033(13) C14 0.0138(15) 0.0133(16) 0.0133(14) 0.0001(12) 0.0092(12) -0.0010(12) C15 0.0075(14) 0.0188(17) 0.0181(15) -0.0016(13) 0.0068(12) 0.0004(12) C16 0.0175(16) 0.0212(19) 0.0247(17) -0.0010(14) 0.0019(13) 0.0069(14) C17 0.0309(19) 0.0146(18) 0.0302(19) 0.0045(15) 0.0042(15) 0.0113(14) C18 0.0242(17) 0.0048(15) 0.0200(16) 0.0031(12) 0.0050(13) 0.0015(12) C19 0.0213(16) 0.0047(15) 0.0218(16) -0.0012(12) 0.0073(13) -0.0047(12) C20 0.0321(19) 0.0166(18) 0.0234(18) -0.0069(14) 0.0072(15) -0.0046(15) C21 0.0232(16) 0.0190(18) 0.0136(15) -0.0036(13) 0.0065(13) 0.0001(13) Cl1 0.0369(5) 0.0545(7) 0.0237(5) 0.0028(4) 0.0060(4) 0.0083(5) C22A 0.0285(19) 0.032(2) 0.0177(17) -0.0042(15) 0.0021(14) -0.0082(16) Cl2A 0.068(8) 0.025(4) 0.039(5) -0.003(3) -0.022(5) 0.001(4) C22B 0.0285(19) 0.032(2) 0.0177(17) -0.0042(15) 0.0021(14) -0.0082(16) Cl2B 0.104(5) 0.0281(14) 0.0312(13) -0.0055(10) 0.005(2) -0.030(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 B1 2.156(3) . ? Ir1 C14 2.160(3) . ? Ir1 C15 2.175(3) . ? Ir1 C18 2.316(3) . ? Ir1 C19 2.331(3) . ? Ir1 S1 2.3938(7) . ? Ir1 S2 2.4627(7) . ? Ir1 H1 1.50(3) . ? S1 C1 1.712(3) . ? S2 C5 1.710(3) . ? N1 C1 1.344(4) . ? N1 C2 1.391(4) . ? N1 B1 1.584(4) . ? N2 C1 1.354(4) . ? N2 C3 1.387(4) . ? N2 C4 1.458(4) . ? N3 C5 1.346(4) . ? N3 C6 1.393(4) . ? N3 B1 1.570(4) . ? N4 C5 1.357(4) . ? N4 C7 1.387(4) . ? N4 C8 1.454(4) . ? N5 C9 1.371(4) . ? N5 N6 1.381(3) . ? N5 B1 1.551(4) . ? N6 C11 1.333(4) . ? C2 C3 1.352(4) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 C7 1.351(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.383(4) . ? C9 C12 1.490(4) . ? C10 C11 1.401(4) . ? C10 H10 0.9500 . ? C11 C13 1.504(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.402(4) . ? C14 C21 1.519(4) . ? C14 H14 1.0000 . ? C15 C16 1.526(4) . ? C15 H15 1.0000 . ? C16 C17 1.535(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.518(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.372(4) . ? C18 H18 1.0000 . ? C19 C20 1.521(4) . ? C19 H19 1.0000 . ? C20 C21 1.543(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? Cl1 C22A 1.770(4) . ? C22A Cl2A 1.768(12) . ? C22A H22A 0.9900 . ? C22A H22B 0.9900 . ? 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 B1 Ir1 C14 91.08(11) . . ? B1 Ir1 C15 93.04(12) . . ? C14 Ir1 C15 37.74(11) . . ? B1 Ir1 C18 160.21(12) . . ? C14 Ir1 C18 93.99(11) . . ? C15 Ir1 C18 79.59(11) . . ? B1 Ir1 C19 164.78(11) . . ? C14 Ir1 C19 79.76(11) . . ? C15 Ir1 C19 87.14(11) . . ? C18 Ir1 C19 34.33(11) . . ? B1 Ir1 S1 86.51(8) . . ? C14 Ir1 S1 170.74(8) . . ? C15 Ir1 S1 151.28(8) . . ? C18 Ir1 S1 91.25(8) . . ? C19 Ir1 S1 100.58(8) . . ? B1 Ir1 S2 85.48(8) . . ? C14 Ir1 S2 82.18(8) . . ? C15 Ir1 S2 119.91(8) . . ? C18 Ir1 S2 114.15(8) . . ? C19 Ir1 S2 81.27(8) . . ? S1 Ir1 S2 88.71(3) . . ? B1 Ir1 H1 84.3(12) . . ? C14 Ir1 H1 106.9(12) . . ? C15 Ir1 H1 69.6(12) . . ? C18 Ir1 H1 75.9(12) . . ? C19 Ir1 H1 109.9(12) . . ? S1 Ir1 H1 81.8(12) . . ? S2 Ir1 H1 166.4(12) . . ? C1 S1 Ir1 97.95(9) . . ? C5 S2 Ir1 96.34(10) . . ? C1 N1 C2 108.2(2) . . ? C1 N1 B1 121.3(2) . . ? C2 N1 B1 130.0(2) . . ? C1 N2 C3 108.4(2) . . ? C1 N2 C4 125.4(3) . . ? C3 N2 C4 126.2(3) . . ? C5 N3 C6 107.9(2) . . ? C5 N3 B1 121.8(2) . . ? C6 N3 B1 129.8(2) . . ? C5 N4 C7 108.1(2) . . ? C5 N4 C8 125.5(3) . . ? C7 N4 C8 126.1(3) . . ? C9 N5 N6 109.9(2) . . ? C9 N5 B1 130.2(2) . . ? N6 N5 B1 119.8(2) . . ? C11 N6 N5 106.1(2) . . ? N5 B1 N3 106.5(2) . . ? N5 B1 N1 106.0(2) . . ? N3 B1 N1 105.4(2) . . ? N5 B1 Ir1 119.73(19) . . ? N3 B1 Ir1 109.42(19) . . ? N1 B1 Ir1 108.82(19) . . ? N1 C1 N2 108.4(3) . . ? N1 C1 S1 123.7(2) . . ? N2 C1 S1 127.9(2) . . ? C3 C2 N1 107.8(3) . . ? C3 C2 H2 126.1 . . ? N1 C2 H2 126.1 . . ? C2 C3 N2 107.3(3) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N4 108.6(2) . . ? N3 C5 S2 124.5(2) . . ? N4 C5 S2 126.9(2) . . ? C7 C6 N3 107.9(3) . . ? C7 C6 H6 126.0 . . ? N3 C6 H6 126.0 . . ? C6 C7 N4 107.5(3) . . ? C6 C7 H7 126.3 . . ? N4 C7 H7 126.3 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 C10 107.4(3) . . ? N5 C9 C12 123.9(3) . . ? C10 C9 C12 128.7(3) . . ? C9 C10 C11 105.5(3) . . ? C9 C10 H10 127.2 . . ? C11 C10 H10 127.2 . . ? N6 C11 C10 111.1(3) . . ? N6 C11 C13 120.1(3) . . ? C10 C11 C13 128.8(3) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C21 122.6(3) . . ? C15 C14 Ir1 71.71(16) . . ? C21 C14 Ir1 113.2(2) . . ? C15 C14 H14 114.1 . . ? C21 C14 H14 114.1 . . ? Ir1 C14 H14 114.1 . . ? C14 C15 C16 123.0(3) . . ? C14 C15 Ir1 70.55(16) . . ? C16 C15 Ir1 114.6(2) . . ? C14 C15 H15 113.9 . . ? C16 C15 H15 113.9 . . ? Ir1 C15 H15 113.9 . . ? C15 C16 C17 114.5(3) . . ? C15 C16 H16A 108.6 . . ? C17 C16 H16A 108.6 . . ? C15 C16 H16B 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C16 114.1(3) . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? C16 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C17 125.3(3) . . ? C19 C18 Ir1 73.43(17) . . ? C17 C18 Ir1 107.7(2) . . ? C19 C18 H18 114.2 . . ? C17 C18 H18 114.2 . . ? Ir1 C18 H18 114.2 . . ? C18 C19 C20 123.3(3) . . ? C18 C19 Ir1 72.24(17) . . ? C20 C19 Ir1 110.3(2) . . ? C18 C19 H19 114.5 . . ? C20 C19 H19 114.5 . . ? Ir1 C19 H19 114.5 . . ? C19 C20 C21 115.0(3) . . ? C19 C20 H20A 108.5 . . ? C21 C20 H20A 108.5 . . ? C19 C20 H20B 108.5 . . ? C21 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C14 C21 C20 114.8(3) . . ? C14 C21 H21A 108.6 . . ? C20 C21 H21A 108.6 . . ? C14 C21 H21B 108.6 . . ? C20 C21 H21B 108.6 . . ? H21A C21 H21B 107.5 . . ? Cl2A C22A Cl1 114.3(5) . . ? Cl2A C22A H22A 108.7 . . ? Cl1 C22A H22A 108.7 . . ? Cl2A C22A H22B 108.7 . . ? Cl1 C22A H22B 108.7 . . ? H22A C22A H22B 107.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag B1 Ir1 S1 C1 -8.17(12) . . . . ? C15 Ir1 S1 C1 81.8(2) . . . . ? C18 Ir1 S1 C1 152.16(12) . . . . ? C19 Ir1 S1 C1 -174.58(12) . . . . ? S2 Ir1 S1 C1 -93.71(10) . . . . ? B1 Ir1 S2 C5 11.28(13) . . . . ? C14 Ir1 S2 C5 -80.44(13) . . . . ? C15 Ir1 S2 C5 -79.64(14) . . . . ? C18 Ir1 S2 C5 -171.32(13) . . . . ? C19 Ir1 S2 C5 -161.21(12) . . . . ? S1 Ir1 S2 C5 97.88(10) . . . . ? C9 N5 N6 C11 -1.4(3) . . . . ? B1 N5 N6 C11 -177.9(2) . . . . ? C9 N5 B1 N3 162.3(3) . . . . ? N6 N5 B1 N3 -22.0(3) . . . . ? C9 N5 B1 N1 50.4(4) . . . . ? N6 N5 B1 N1 -133.9(2) . . . . ? C9 N5 B1 Ir1 -73.1(4) . . . . ? N6 N5 B1 Ir1 102.7(3) . . . . ? C5 N3 B1 N5 145.6(2) . . . . ? C6 N3 B1 N5 -43.4(4) . . . . ? C5 N3 B1 N1 -102.1(3) . . . . ? C6 N3 B1 N1 69.0(3) . . . . ? C5 N3 B1 Ir1 14.8(3) . . . . ? C6 N3 B1 Ir1 -174.2(2) . . . . ? C1 N1 B1 N5 -143.5(2) . . . . ? C2 N1 B1 N5 45.7(4) . . . . ? C1 N1 B1 N3 103.8(3) . . . . ? C2 N1 B1 N3 -67.1(3) . . . . ? C1 N1 B1 Ir1 -13.5(3) . . . . ? C2 N1 B1 Ir1 175.7(2) . . . . ? C14 Ir1 B1 N5 -55.4(2) . . . . ? C15 Ir1 B1 N5 -17.7(2) . . . . ? C18 Ir1 B1 N5 49.6(4) . . . . ? C19 Ir1 B1 N5 -108.0(4) . . . . ? S1 Ir1 B1 N5 133.6(2) . . . . ? S2 Ir1 B1 N5 -137.4(2) . . . . ? C14 Ir1 B1 N3 67.91(19) . . . . ? C15 Ir1 B1 N3 105.63(19) . . . . ? C18 Ir1 B1 N3 172.9(3) . . . . ? C19 Ir1 B1 N3 15.3(5) . . . . ? S1 Ir1 B1 N3 -103.14(17) . . . . ? S2 Ir1 B1 N3 -14.15(17) . . . . ? C14 Ir1 B1 N1 -177.45(19) . . . . ? C15 Ir1 B1 N1 -139.73(18) . . . . ? C18 Ir1 B1 N1 -72.5(4) . . . . ? C19 Ir1 B1 N1 130.0(4) . . . . ? S1 Ir1 B1 N1 11.50(16) . . . . ? S2 Ir1 B1 N1 100.49(17) . . . . ? C2 N1 C1 N2 0.4(3) . . . . ? B1 N1 C1 N2 -172.3(2) . . . . ? C2 N1 C1 S1 178.9(2) . . . . ? B1 N1 C1 S1 6.3(4) . . . . ? C3 N2 C1 N1 -0.6(3) . . . . ? C4 N2 C1 N1 179.7(3) . . . . ? C3 N2 C1 S1 -179.1(2) . . . . ? C4 N2 C1 S1 1.2(4) . . . . ? Ir1 S1 C1 N1 3.6(2) . . . . ? Ir1 S1 C1 N2 -178.2(2) . . . . ? C1 N1 C2 C3 0.0(3) . . . . ? B1 N1 C2 C3 171.8(3) . . . . ? N1 C2 C3 N2 -0.4(3) . . . . ? C1 N2 C3 C2 0.6(3) . . . . ? C4 N2 C3 C2 -179.7(3) . . . . ? C6 N3 C5 N4 1.2(3) . . . . ? B1 N3 C5 N4 174.0(2) . . . . ? C6 N3 C5 S2 -176.6(2) . . . . ? B1 N3 C5 S2 -3.8(4) . . . . ? C7 N4 C5 N3 -1.1(3) . . . . ? C8 N4 C5 N3 173.5(3) . . . . ? C7 N4 C5 S2 176.7(2) . . . . ? C8 N4 C5 S2 -8.7(4) . . . . ? Ir1 S2 C5 N3 -7.5(2) . . . . ? Ir1 S2 C5 N4 175.1(2) . . . . ? C5 N3 C6 C7 -1.0(3) . . . . ? B1 N3 C6 C7 -173.0(3) . . . . ? N3 C6 C7 N4 0.3(3) . . . . ? C5 N4 C7 C6 0.4(3) . . . . ? C8 N4 C7 C6 -174.1(3) . . . . ? N6 N5 C9 C10 1.3(3) . . . . ? B1 N5 C9 C10 177.3(3) . . . . ? N6 N5 C9 C12 -177.2(3) . . . . ? B1 N5 C9 C12 -1.1(5) . . . . ? N5 C9 C10 C11 -0.6(3) . . . . ? C12 C9 C10 C11 177.7(3) . . . . ? N5 N6 C11 C10 1.0(3) . . . . ? N5 N6 C11 C13 -179.0(3) . . . . ? C9 C10 C11 N6 -0.3(4) . . . . ? C9 C10 C11 C13 179.8(3) . . . . ? B1 Ir1 C14 C15 93.58(19) . . . . ? C18 Ir1 C14 C15 -67.29(19) . . . . ? C19 Ir1 C14 C15 -98.7(2) . . . . ? S2 Ir1 C14 C15 178.86(18) . . . . ? B1 Ir1 C14 C21 -148.1(2) . . . . ? C15 Ir1 C14 C21 118.4(3) . . . . ? C18 Ir1 C14 C21 51.1(2) . . . . ? C19 Ir1 C14 C21 19.7(2) . . . . ? S2 Ir1 C14 C21 -62.8(2) . . . . ? C21 C14 C15 C16 0.9(4) . . . . ? Ir1 C14 C15 C16 107.2(3) . . . . ? C21 C14 C15 Ir1 -106.4(3) . . . . ? B1 Ir1 C15 C14 -87.83(19) . . . . ? C18 Ir1 C15 C14 110.67(19) . . . . ? C19 Ir1 C15 C14 76.92(19) . . . . ? S1 Ir1 C15 C14 -176.12(15) . . . . ? S2 Ir1 C15 C14 -1.3(2) . . . . ? B1 Ir1 C15 C16 153.9(2) . . . . ? C14 Ir1 C15 C16 -118.2(3) . . . . ? C18 Ir1 C15 C16 -7.6(2) . . . . ? C19 Ir1 C15 C16 -41.3(2) . . . . ? S1 Ir1 C15 C16 65.6(3) . . . . ? S2 Ir1 C15 C16 -119.5(2) . . . . ? C14 C15 C16 C17 -90.8(4) . . . . ? Ir1 C15 C16 C17 -8.9(4) . . . . ? C15 C16 C17 C18 29.7(4) . . . . ? C16 C17 C18 C19 47.9(4) . . . . ? C16 C17 C18 Ir1 -34.0(3) . . . . ? B1 Ir1 C18 C19 -169.8(3) . . . . ? C14 Ir1 C18 C19 -65.3(2) . . . . ? C15 Ir1 C18 C19 -100.3(2) . . . . ? S1 Ir1 C18 C19 107.08(18) . . . . ? S2 Ir1 C18 C19 17.9(2) . . . . ? B1 Ir1 C18 C17 -47.2(4) . . . . ? C14 Ir1 C18 C17 57.3(2) . . . . ? C15 Ir1 C18 C17 22.2(2) . . . . ? C19 Ir1 C18 C17 122.6(3) . . . . ? S1 Ir1 C18 C17 -130.4(2) . . . . ? S2 Ir1 C18 C17 140.49(19) . . . . ? C17 C18 C19 C20 2.8(5) . . . . ? Ir1 C18 C19 C20 103.0(3) . . . . ? C17 C18 C19 Ir1 -100.2(3) . . . . ? B1 Ir1 C19 C18 166.7(4) . . . . ? C14 Ir1 C19 C18 112.9(2) . . . . ? C15 Ir1 C19 C18 75.7(2) . . . . ? S1 Ir1 C19 C18 -76.46(18) . . . . ? S2 Ir1 C19 C18 -163.49(19) . . . . ? B1 Ir1 C19 C20 47.0(5) . . . . ? C14 Ir1 C19 C20 -6.8(2) . . . . ? C15 Ir1 C19 C20 -44.1(2) . . . . ? C18 Ir1 C19 C20 -119.8(3) . . . . ? S1 Ir1 C19 C20 163.8(2) . . . . ? S2 Ir1 C19 C20 76.7(2) . . . . ? C18 C19 C20 C21 -88.7(4) . . . . ? Ir1 C19 C20 C21 -7.1(3) . . . . ? C15 C14 C21 C20 52.3(4) . . . . ? Ir1 C14 C21 C20 -30.2(3) . . . . ? C19 C20 C21 C14 24.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.786 _refine_diff_density_min -0.908 _refine_diff_density_rms 0.124 data_5 _database_code_depnum_ccdc_archive 'CCDC 804001' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 B Ir N6 O2 S2, C H2 Cl2' _chemical_formula_sum 'C16 H20 B Cl2 Ir N6 O2 S2' _chemical_formula_weight 666.41 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' 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8351(2) _cell_length_b 10.3766(2) _cell_length_c 13.2958(4) _cell_angle_alpha 73.239(1) _cell_angle_beta 84.423(1) _cell_angle_gamma 85.728(1) _cell_volume 1160.24(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16907 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.908 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 6.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68485 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type ; Bruker-Nonius APEX II CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 20337 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.58 _reflns_number_total 5330 _reflns_number_gt 4779 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement ; DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) ; _computing_data_reduction ; DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+4.9979P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5330 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 0.67645(2) 0.16222(2) 0.134275(16) 0.01698(7) Uani 1 1 d . . . H1 H 0.811(6) 0.153(5) 0.057(4) 0.020 Uiso 1 1 d . . . S1 S 0.72719(15) 0.39799(12) 0.08879(10) 0.0196(3) Uani 1 1 d . . . S2 S 0.48325(14) 0.18525(13) 0.27542(10) 0.0197(3) Uani 1 1 d . . . N1 N 0.9430(5) 0.2649(4) 0.2175(3) 0.0165(9) Uani 1 1 d . . . N2 N 0.9784(5) 0.4797(4) 0.1549(4) 0.0197(10) Uani 1 1 d . . . N3 N 0.7587(5) 0.1353(4) 0.3591(3) 0.0147(9) Uani 1 1 d . . . N4 N 0.5704(5) 0.1571(4) 0.4723(3) 0.0170(9) Uani 1 1 d . . . N5 N 0.9574(5) 0.0105(4) 0.2710(3) 0.0162(9) Uani 1 1 d . . . N6 N 0.9200(5) -0.1004(4) 0.3547(3) 0.0162(9) Uani 1 1 d . . . O1 O 0.6833(5) -0.1405(4) 0.2038(4) 0.0358(11) Uani 1 1 d . . . O2 O 0.4659(7) 0.2225(6) -0.0489(4) 0.0613(16) Uani 1 1 d . . . B1 B 0.8470(6) 0.1359(5) 0.2518(4) 0.0133(11) Uani 1 1 d . . . C1 C 0.8886(5) 0.3816(5) 0.1546(4) 0.0157(10) Uani 1 1 d . . . C2 C 1.0724(6) 0.2916(6) 0.2584(5) 0.0229(12) Uani 1 1 d . . . H2 H 1.1340 0.2275 0.3054 0.027 Uiso 1 1 calc R . . C3 C 1.0949(6) 0.4241(5) 0.2197(5) 0.0236(12) Uani 1 1 d . . . H3 H 1.1751 0.4708 0.2339 0.028 Uiso 1 1 calc R . . C4 C 0.9517(7) 0.6224(5) 0.1034(5) 0.0254(13) Uani 1 1 d . . . H4A H 0.8807 0.6339 0.0489 0.038 Uiso 1 1 calc R . . H4B H 1.0483 0.6619 0.0711 0.038 Uiso 1 1 calc R . . H4C H 0.9080 0.6677 0.1556 0.038 Uiso 1 1 calc R . . C5 C 0.6072(6) 0.1588(5) 0.3721(4) 0.0154(10) Uani 1 1 d . . . C6 C 0.8181(6) 0.1207(5) 0.4549(4) 0.0166(10) Uani 1 1 d . . . H6 H 0.9225 0.1044 0.4685 0.020 Uiso 1 1 calc R . . C7 C 0.7009(6) 0.1339(5) 0.5259(4) 0.0180(11) Uani 1 1 d . . . H7 H 0.7072 0.1284 0.5979 0.022 Uiso 1 1 calc R . . C8 C 0.4165(6) 0.1848(6) 0.5165(5) 0.0241(12) Uani 1 1 d . . . H8A H 0.3927 0.2821 0.4956 0.036 Uiso 1 1 calc R . . H8B H 0.4119 0.1510 0.5935 0.036 Uiso 1 1 calc R . . H8C H 0.3425 0.1396 0.4898 0.036 Uiso 1 1 calc R . . C9 C 1.0736(6) -0.0241(5) 0.2064(4) 0.0200(11) Uani 1 1 d . . . C10 C 1.1124(6) -0.1578(5) 0.2481(4) 0.0198(11) Uani 1 1 d . . . H10 H 1.1895 -0.2105 0.2211 0.024 Uiso 1 1 calc R . . C11 C 1.0142(6) -0.2003(5) 0.3395(4) 0.0188(11) Uani 1 1 d . . . C12 C 1.1405(7) 0.0713(6) 0.1076(5) 0.0296(14) Uani 1 1 d . . . H12A H 1.2155 0.0221 0.0714 0.044 Uiso 1 1 calc R . . H12B H 1.1904 0.1422 0.1254 0.044 Uiso 1 1 calc R . . H12C H 1.0594 0.1120 0.0614 0.044 Uiso 1 1 calc R . . C13 C 1.0076(6) -0.3365(5) 0.4201(4) 0.0223(12) Uani 1 1 d . . . H13A H 1.0855 -0.3452 0.4696 0.033 Uiso 1 1 calc R . . H13B H 1.0262 -0.4074 0.3844 0.033 Uiso 1 1 calc R . . H13C H 0.9068 -0.3455 0.4586 0.033 Uiso 1 1 calc R . . C14 C 0.6783(7) -0.0256(6) 0.1773(5) 0.0266(13) Uani 1 1 d . . . C15 C 0.5373(7) 0.2024(6) 0.0198(5) 0.0309(14) Uani 1 1 d . . . C16 C 0.5529(6) 0.5372(6) 0.2828(5) 0.0272(13) Uani 1 1 d . . . H16A H 0.5312 0.4661 0.2507 0.033 Uiso 1 1 calc R . . H16B H 0.5779 0.6191 0.2250 0.033 Uiso 1 1 calc R . . Cl1 Cl 0.71005(16) 0.48350(16) 0.35806(12) 0.0326(3) Uani 1 1 d . . . Cl2 Cl 0.38948(17) 0.57260(17) 0.35918(14) 0.0404(4) 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 0.02010(11) 0.01819(11) 0.01328(11) -0.00450(7) -0.00327(7) -0.00226(7) S1 0.0222(6) 0.0168(6) 0.0180(7) -0.0017(5) -0.0041(5) 0.0007(5) S2 0.0152(6) 0.0257(7) 0.0172(7) -0.0040(5) -0.0024(5) -0.0007(5) N1 0.015(2) 0.017(2) 0.017(2) -0.0043(17) 0.0001(17) -0.0009(16) N2 0.019(2) 0.014(2) 0.025(2) -0.0046(18) 0.0053(18) -0.0050(17) N3 0.015(2) 0.0133(19) 0.015(2) -0.0039(16) -0.0025(17) 0.0008(16) N4 0.020(2) 0.018(2) 0.014(2) -0.0072(17) -0.0005(17) -0.0015(17) N5 0.019(2) 0.015(2) 0.013(2) -0.0038(17) -0.0001(17) 0.0028(16) N6 0.018(2) 0.014(2) 0.015(2) -0.0032(17) -0.0015(17) -0.0017(16) O1 0.059(3) 0.017(2) 0.035(3) -0.0092(18) -0.015(2) -0.0086(19) O2 0.080(4) 0.070(4) 0.035(3) 0.001(3) -0.039(3) -0.025(3) B1 0.013(2) 0.014(3) 0.010(3) 0.001(2) -0.003(2) 0.004(2) C1 0.016(2) 0.014(2) 0.016(3) -0.0035(19) 0.004(2) -0.0040(18) C2 0.015(2) 0.027(3) 0.028(3) -0.007(2) -0.006(2) -0.003(2) C3 0.019(3) 0.026(3) 0.028(3) -0.011(2) 0.000(2) -0.006(2) C4 0.031(3) 0.013(2) 0.030(3) -0.003(2) 0.008(3) -0.008(2) C5 0.020(2) 0.008(2) 0.016(3) 0.0005(18) -0.004(2) -0.0013(18) C6 0.015(2) 0.016(2) 0.021(3) -0.006(2) -0.006(2) 0.0006(19) C7 0.025(3) 0.017(2) 0.013(2) -0.004(2) -0.004(2) -0.002(2) C8 0.020(3) 0.031(3) 0.024(3) -0.013(2) 0.007(2) -0.006(2) C9 0.019(3) 0.017(2) 0.024(3) -0.006(2) -0.003(2) -0.002(2) C10 0.021(3) 0.017(2) 0.021(3) -0.007(2) 0.000(2) 0.004(2) C11 0.021(3) 0.013(2) 0.023(3) -0.003(2) -0.010(2) 0.0009(19) C12 0.028(3) 0.028(3) 0.027(3) -0.005(3) 0.009(2) 0.006(2) C13 0.024(3) 0.016(2) 0.027(3) -0.005(2) -0.007(2) -0.002(2) C14 0.031(3) 0.033(3) 0.021(3) -0.012(3) -0.009(2) -0.007(2) C15 0.032(3) 0.037(3) 0.026(3) -0.010(3) -0.006(3) -0.013(3) C16 0.027(3) 0.032(3) 0.024(3) -0.009(2) -0.004(2) 0.002(2) Cl1 0.0253(7) 0.0426(8) 0.0309(8) -0.0119(7) -0.0067(6) 0.0039(6) Cl2 0.0294(8) 0.0499(10) 0.0445(10) -0.0219(8) -0.0013(7) 0.0132(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C14 1.866(6) . ? Ir1 C15 1.980(6) . ? Ir1 B1 2.222(6) . ? Ir1 S1 2.4102(13) . ? Ir1 S2 2.4633(13) . ? Ir1 H1 1.51(5) . ? S1 C1 1.718(5) . ? S2 C5 1.719(5) . ? N1 C1 1.343(6) . ? N1 C2 1.391(7) . ? N1 B1 1.569(7) . ? N2 C1 1.337(7) . ? N2 C3 1.389(7) . ? N2 C4 1.454(6) . ? N3 C5 1.345(6) . ? N3 C6 1.390(6) . ? N3 B1 1.557(7) . ? N4 C5 1.335(7) . ? N4 C7 1.384(7) . ? N4 C8 1.469(6) . ? N5 C9 1.369(7) . ? N5 N6 1.385(5) . ? N5 B1 1.542(6) . ? N6 C11 1.330(6) . ? O1 C14 1.141(7) . ? O2 C15 1.122(7) . ? C2 C3 1.345(8) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 C7 1.358(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.368(7) . ? C9 C12 1.497(7) . ? C10 C11 1.402(7) . ? C10 H10 0.9500 . ? C11 C13 1.509(7) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C16 Cl1 1.753(6) . ? C16 Cl2 1.762(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? 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 C14 Ir1 C15 100.5(2) . . ? C14 Ir1 B1 84.5(2) . . ? C15 Ir1 B1 173.7(2) . . ? C14 Ir1 S1 168.21(18) . . ? C15 Ir1 S1 89.53(18) . . ? B1 Ir1 S1 85.11(14) . . ? C14 Ir1 S2 93.50(19) . . ? C15 Ir1 S2 96.86(19) . . ? B1 Ir1 S2 86.53(14) . . ? S1 Ir1 S2 91.49(4) . . ? C14 Ir1 H1 89(2) . . ? C15 Ir1 H1 91(2) . . ? B1 Ir1 H1 86(2) . . ? S1 Ir1 H1 85(2) . . ? S2 Ir1 H1 172(2) . . ? C1 S1 Ir1 97.64(17) . . ? C5 S2 Ir1 96.21(18) . . ? C1 N1 C2 107.8(4) . . ? C1 N1 B1 121.3(4) . . ? C2 N1 B1 129.7(4) . . ? C1 N2 C3 108.7(4) . . ? C1 N2 C4 125.7(5) . . ? C3 N2 C4 125.4(5) . . ? C5 N3 C6 107.7(4) . . ? C5 N3 B1 124.2(4) . . ? C6 N3 B1 127.9(4) . . ? C5 N4 C7 109.4(4) . . ? C5 N4 C8 125.1(4) . . ? C7 N4 C8 125.4(4) . . ? C9 N5 N6 110.2(4) . . ? C9 N5 B1 130.2(4) . . ? N6 N5 B1 118.0(4) . . ? C11 N6 N5 105.0(4) . . ? N5 B1 N3 107.8(4) . . ? N5 B1 N1 108.5(4) . . ? N3 B1 N1 106.5(4) . . ? N5 B1 Ir1 118.6(4) . . ? N3 B1 Ir1 107.6(3) . . ? N1 B1 Ir1 107.3(3) . . ? N2 C1 N1 108.7(5) . . ? N2 C1 S1 127.1(4) . . ? N1 C1 S1 124.2(4) . . ? C3 C2 N1 108.0(5) . . ? C3 C2 H2 126.0 . . ? N1 C2 H2 126.0 . . ? C2 C3 N2 106.9(5) . . ? C2 C3 H3 126.6 . . ? N2 C3 H3 126.6 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N4 C5 N3 108.6(4) . . ? N4 C5 S2 126.2(4) . . ? N3 C5 S2 125.2(4) . . ? C7 C6 N3 108.0(4) . . ? C7 C6 H6 126.0 . . ? N3 C6 H6 126.0 . . ? C6 C7 N4 106.3(5) . . ? C6 C7 H7 126.8 . . ? N4 C7 H7 126.8 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N5 107.7(5) . . ? C10 C9 C12 128.1(5) . . ? N5 C9 C12 124.2(4) . . ? C9 C10 C11 105.2(4) . . ? C9 C10 H10 127.4 . . ? C11 C10 H10 127.4 . . ? N6 C11 C10 111.8(4) . . ? N6 C11 C13 118.8(5) . . ? C10 C11 C13 129.3(5) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 Ir1 178.3(5) . . ? O2 C15 Ir1 175.5(6) . . ? Cl1 C16 Cl2 112.0(3) . . ? Cl1 C16 H16A 109.2 . . ? Cl2 C16 H16A 109.2 . . ? Cl1 C16 H16B 109.2 . . ? Cl2 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 Ir1 S1 C1 -15.6(9) . . . . ? C15 Ir1 S1 C1 -163.7(3) . . . . ? B1 Ir1 S1 C1 13.0(2) . . . . ? S2 Ir1 S1 C1 99.44(18) . . . . ? C14 Ir1 S2 C5 82.0(2) . . . . ? C15 Ir1 S2 C5 -177.0(2) . . . . ? B1 Ir1 S2 C5 -2.3(2) . . . . ? S1 Ir1 S2 C5 -87.34(16) . . . . ? C9 N5 N6 C11 0.0(6) . . . . ? B1 N5 N6 C11 167.1(4) . . . . ? C9 N5 B1 N3 -169.6(5) . . . . ? N6 N5 B1 N3 26.4(6) . . . . ? C9 N5 B1 N1 -54.6(7) . . . . ? N6 N5 B1 N1 141.4(4) . . . . ? C9 N5 B1 Ir1 68.0(6) . . . . ? N6 N5 B1 Ir1 -96.0(5) . . . . ? C5 N3 B1 N5 -134.2(5) . . . . ? C6 N3 B1 N5 50.7(6) . . . . ? C5 N3 B1 N1 109.5(5) . . . . ? C6 N3 B1 N1 -65.6(6) . . . . ? C5 N3 B1 Ir1 -5.3(5) . . . . ? C6 N3 B1 Ir1 179.6(4) . . . . ? C1 N1 B1 N5 151.2(4) . . . . ? C2 N1 B1 N5 -43.6(7) . . . . ? C1 N1 B1 N3 -93.0(5) . . . . ? C2 N1 B1 N3 72.2(6) . . . . ? C1 N1 B1 Ir1 21.9(5) . . . . ? C2 N1 B1 Ir1 -172.8(4) . . . . ? C14 Ir1 B1 N5 32.5(4) . . . . ? S1 Ir1 B1 N5 -141.8(4) . . . . ? S2 Ir1 B1 N5 126.4(4) . . . . ? C14 Ir1 B1 N3 -90.0(3) . . . . ? S1 Ir1 B1 N3 95.7(3) . . . . ? S2 Ir1 B1 N3 3.9(3) . . . . ? C14 Ir1 B1 N1 155.8(4) . . . . ? S1 Ir1 B1 N1 -18.6(3) . . . . ? S2 Ir1 B1 N1 -110.4(3) . . . . ? C3 N2 C1 N1 0.3(6) . . . . ? C4 N2 C1 N1 -174.9(5) . . . . ? C3 N2 C1 S1 178.8(4) . . . . ? C4 N2 C1 S1 3.7(8) . . . . ? C2 N1 C1 N2 -0.2(6) . . . . ? B1 N1 C1 N2 168.0(4) . . . . ? C2 N1 C1 S1 -178.7(4) . . . . ? B1 N1 C1 S1 -10.6(7) . . . . ? Ir1 S1 C1 N2 175.9(4) . . . . ? Ir1 S1 C1 N1 -5.8(4) . . . . ? C1 N1 C2 C3 -0.1(6) . . . . ? B1 N1 C2 C3 -166.9(5) . . . . ? N1 C2 C3 N2 0.3(6) . . . . ? C1 N2 C3 C2 -0.4(6) . . . . ? C4 N2 C3 C2 174.8(5) . . . . ? C7 N4 C5 N3 1.0(5) . . . . ? C8 N4 C5 N3 177.1(4) . . . . ? C7 N4 C5 S2 -179.5(4) . . . . ? C8 N4 C5 S2 -3.4(7) . . . . ? C6 N3 C5 N4 -1.1(5) . . . . ? B1 N3 C5 N4 -177.0(4) . . . . ? C6 N3 C5 S2 179.4(4) . . . . ? B1 N3 C5 S2 3.4(7) . . . . ? Ir1 S2 C5 N4 -179.2(4) . . . . ? Ir1 S2 C5 N3 0.3(4) . . . . ? C5 N3 C6 C7 0.8(5) . . . . ? B1 N3 C6 C7 176.6(4) . . . . ? N3 C6 C7 N4 -0.2(5) . . . . ? C5 N4 C7 C6 -0.4(6) . . . . ? C8 N4 C7 C6 -176.5(5) . . . . ? N6 N5 C9 C10 -0.2(6) . . . . ? B1 N5 C9 C10 -165.2(5) . . . . ? N6 N5 C9 C12 179.1(5) . . . . ? B1 N5 C9 C12 14.1(9) . . . . ? N5 C9 C10 C11 0.2(6) . . . . ? C12 C9 C10 C11 -179.0(6) . . . . ? N5 N6 C11 C10 0.1(6) . . . . ? N5 N6 C11 C13 177.7(4) . . . . ? C9 C10 C11 N6 -0.2(6) . . . . ? C9 C10 C11 C13 -177.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.851 _refine_diff_density_min -0.903 _refine_diff_density_rms 0.198 data_7 _database_code_depnum_ccdc_archive 'CCDC 804002' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H33 B Ir N6 O P S2, 2(C H2 Cl2)' _chemical_formula_sum 'C34 H37 B Cl4 Ir N6 O P S2' _chemical_formula_weight 985.60 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7634(4) _cell_length_b 12.8390(5) _cell_length_c 14.8572(6) _cell_angle_alpha 85.9710(10) _cell_angle_beta 72.1290(10) _cell_angle_gamma 67.116(2) _cell_volume 1964.45(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 49561 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 3.854 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7404 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type ; Bruker-Nonius APEX II CCD camera on \k-goniostat' ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 29754 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.54 _reflns_number_total 8969 _reflns_number_gt 7993 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement ; DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) ; _computing_data_reduction ; DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+9.6667P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8969 _refine_ls_number_parameters 458 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 0.002151(16) 0.289777(15) 0.748018(13) 0.01739(6) Uani 1 1 d D . . H1 H -0.014(5) 0.374(3) 0.674(3) 0.021 Uiso 1 1 d D . . N1 N -0.1673(3) 0.5112(3) 0.8702(3) 0.0207(8) Uani 1 1 d . . . N2 N -0.0641(4) 0.6010(4) 0.9105(3) 0.0259(9) Uani 1 1 d . . . N3 N -0.2228(3) 0.3465(3) 0.9345(3) 0.0192(8) Uani 1 1 d . . . N4 N -0.1977(4) 0.2243(3) 1.0436(3) 0.0226(8) Uani 1 1 d . . . N5 N -0.3056(3) 0.4494(3) 0.8039(3) 0.0189(8) Uani 1 1 d . . . N6 N -0.3931(3) 0.3975(3) 0.8301(3) 0.0209(8) Uani 1 1 d . . . O1 O -0.1553(4) 0.2074(3) 0.6699(3) 0.0373(10) Uani 1 1 d . . . P1 P 0.21589(11) 0.17284(10) 0.65105(9) 0.0192(2) Uani 1 1 d . . . S1 S 0.09253(11) 0.39802(10) 0.81033(9) 0.0224(2) Uani 1 1 d . . . S2 S 0.00565(11) 0.16495(10) 0.88055(9) 0.0248(3) Uani 1 1 d . . . B1 B -0.1876(4) 0.4065(4) 0.8406(4) 0.0173(10) Uani 1 1 d . . . C1 C -0.0500(4) 0.5068(4) 0.8658(3) 0.0205(9) Uani 1 1 d . . . C2 C -0.2592(5) 0.6118(4) 0.9213(4) 0.0278(11) Uani 1 1 d . . . H2 H -0.3505 0.6367 0.9360 0.033 Uiso 1 1 calc R . . C3 C -0.1959(5) 0.6668(4) 0.9458(4) 0.0283(11) Uani 1 1 d . . . H3 H -0.2340 0.7375 0.9808 0.034 Uiso 1 1 calc R . . C4 C 0.0410(5) 0.6289(5) 0.9191(4) 0.0298(11) Uani 1 1 d . . . H4A H 0.1061 0.5615 0.9352 0.045 Uiso 1 1 calc R . . H4B H 0.0067 0.6888 0.9691 0.045 Uiso 1 1 calc R . . H4C H 0.0811 0.6552 0.8588 0.045 Uiso 1 1 calc R . . C5 C -0.1434(4) 0.2463(4) 0.9543(3) 0.0207(9) Uani 1 1 d . . . C6 C -0.3297(4) 0.3897(4) 1.0147(3) 0.0235(10) Uani 1 1 d . . . H6 H -0.4009 0.4601 1.0207 0.028 Uiso 1 1 calc R . . C7 C -0.3146(4) 0.3143(4) 1.0822(3) 0.0234(10) Uani 1 1 d . . . H7 H -0.3728 0.3213 1.1443 0.028 Uiso 1 1 calc R . . C8 C -0.1394(5) 0.1218(4) 1.0905(4) 0.0327(12) Uani 1 1 d . . . H8A H -0.1478 0.0576 1.0652 0.049 Uiso 1 1 calc R . . H8B H -0.1838 0.1331 1.1588 0.049 Uiso 1 1 calc R . . H8C H -0.0475 0.1062 1.0789 0.049 Uiso 1 1 calc R . . C9 C -0.3310(4) 0.5220(4) 0.7346(3) 0.0223(10) Uani 1 1 d . . . C10 C -0.4373(4) 0.5171(4) 0.7167(3) 0.0254(10) Uani 1 1 d . . . H10 H -0.4784 0.5582 0.6720 0.030 Uiso 1 1 calc R . . C11 C -0.4719(4) 0.4395(4) 0.7779(3) 0.0222(10) Uani 1 1 d . . . C12 C -0.2511(5) 0.5895(4) 0.6884(4) 0.0295(11) Uani 1 1 d . . . H12A H -0.2672 0.6499 0.7332 0.044 Uiso 1 1 calc R . . H12B H -0.2749 0.6229 0.6322 0.044 Uiso 1 1 calc R . . H12C H -0.1590 0.5397 0.6698 0.044 Uiso 1 1 calc R . . C13 C -0.5814(5) 0.4024(5) 0.7878(4) 0.0297(11) Uani 1 1 d . . . H13A H -0.5515 0.3374 0.7435 0.045 Uiso 1 1 calc R . . H13B H -0.6532 0.4649 0.7735 0.045 Uiso 1 1 calc R . . H13C H -0.6108 0.3807 0.8527 0.045 Uiso 1 1 calc R . . C14 C -0.0918(5) 0.2362(4) 0.6999(4) 0.0275(11) Uani 1 1 d . . . C15 C 0.2161(4) 0.1067(4) 0.5461(3) 0.0226(10) Uani 1 1 d . . . C16 C 0.1533(4) 0.0300(4) 0.5587(4) 0.0259(11) Uani 1 1 d . . . H16 H 0.1126 0.0142 0.6210 0.031 Uiso 1 1 calc R . . C17 C 0.1505(5) -0.0216(4) 0.4823(4) 0.0294(11) Uani 1 1 d . . . H17 H 0.1122 -0.0760 0.4915 0.035 Uiso 1 1 calc R . . C18 C 0.2034(5) 0.0057(5) 0.3916(4) 0.0345(13) Uani 1 1 d . . . H18 H 0.1986 -0.0281 0.3387 0.041 Uiso 1 1 calc R . . C19 C 0.2632(5) 0.0820(5) 0.3774(4) 0.0354(13) Uani 1 1 d . . . H19 H 0.2988 0.1011 0.3150 0.043 Uiso 1 1 calc R . . C20 C 0.2709(5) 0.1308(4) 0.4551(4) 0.0262(10) Uani 1 1 d . . . H20 H 0.3145 0.1813 0.4452 0.031 Uiso 1 1 calc R . . C21 C 0.3267(4) 0.2453(4) 0.6019(3) 0.0197(9) Uani 1 1 d . . . C22 C 0.4594(4) 0.1934(4) 0.5896(4) 0.0250(10) Uani 1 1 d . . . H22 H 0.4946 0.1184 0.6086 0.030 Uiso 1 1 calc R . . C23 C 0.5403(5) 0.2502(4) 0.5497(4) 0.0282(11) Uani 1 1 d . . . H23 H 0.6300 0.2152 0.5435 0.034 Uiso 1 1 calc R . . C24 C 0.4903(5) 0.3579(4) 0.5190(4) 0.0285(11) Uani 1 1 d . . . H24 H 0.5461 0.3959 0.4901 0.034 Uiso 1 1 calc R . . C25 C 0.3579(5) 0.4109(4) 0.5303(4) 0.0267(11) Uani 1 1 d . . . H25 H 0.3234 0.4852 0.5098 0.032 Uiso 1 1 calc R . . C26 C 0.2772(4) 0.3543(4) 0.5716(3) 0.0225(10) Uani 1 1 d . . . H26 H 0.1871 0.3903 0.5793 0.027 Uiso 1 1 calc R . . C27 C 0.3116(4) 0.0540(4) 0.7072(4) 0.0226(10) Uani 1 1 d . . . C28 C 0.3725(4) -0.0569(4) 0.6683(4) 0.0270(11) Uani 1 1 d . . . H28 H 0.3654 -0.0736 0.6094 0.032 Uiso 1 1 calc R . . C29 C 0.4440(5) -0.1440(4) 0.7151(4) 0.0322(12) Uani 1 1 d . . . H29 H 0.4834 -0.2197 0.6890 0.039 Uiso 1 1 calc R . . C30 C 0.4568(5) -0.1194(5) 0.7989(4) 0.0334(12) Uani 1 1 d . . . H30 H 0.5064 -0.1783 0.8301 0.040 Uiso 1 1 calc R . . C31 C 0.3982(5) -0.0092(5) 0.8386(4) 0.0356(12) Uani 1 1 d . . . H31 H 0.4079 0.0071 0.8966 0.043 Uiso 1 1 calc R . . C32 C 0.3254(5) 0.0766(4) 0.7930(4) 0.0286(11) Uani 1 1 d . . . H32 H 0.2845 0.1517 0.8204 0.034 Uiso 1 1 calc R . . C33 C 0.9588(8) 0.3319(7) 0.3484(5) 0.063(2) Uani 1 1 d . . . H33A H 0.9368 0.4059 0.3190 0.076 Uiso 1 1 calc R . . H33B H 1.0484 0.2826 0.3123 0.076 Uiso 1 1 calc R . . Cl1 Cl 0.8517(3) 0.2699(2) 0.34130(19) 0.0907(8) Uani 1 1 d . . . Cl2 Cl 0.95095(18) 0.35189(18) 0.46723(14) 0.0680(6) Uani 1 1 d . . . C34 C 0.3424(8) 0.8714(6) 0.1325(7) 0.075(3) Uani 1 1 d . . . H34A H 0.3609 0.8656 0.1937 0.089 Uiso 1 1 calc R . . H34B H 0.3095 0.8123 0.1283 0.089 Uiso 1 1 calc R . . Cl3 Cl 0.48475(17) 0.84519(15) 0.04181(13) 0.0549(4) Uani 1 1 d . . . Cl4 Cl 0.22223(19) 1.0038(2) 0.13109(16) 0.0743(6) 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 0.01526(8) 0.01660(9) 0.01817(9) -0.00167(6) -0.00200(6) -0.00586(6) N1 0.0164(17) 0.0182(19) 0.025(2) -0.0061(16) -0.0041(15) -0.0050(15) N2 0.026(2) 0.025(2) 0.028(2) -0.0071(18) -0.0032(17) -0.0140(17) N3 0.0169(17) 0.0200(19) 0.0186(19) -0.0018(15) -0.0027(15) -0.0066(15) N4 0.0220(19) 0.020(2) 0.021(2) 0.0017(16) -0.0020(16) -0.0063(16) N5 0.0177(17) 0.0172(19) 0.021(2) -0.0024(15) -0.0040(15) -0.0074(15) N6 0.0170(17) 0.024(2) 0.022(2) -0.0023(16) -0.0036(15) -0.0096(15) O1 0.0304(19) 0.041(2) 0.043(2) -0.0166(19) -0.0051(17) -0.0178(17) P1 0.0164(5) 0.0175(6) 0.0203(6) -0.0010(5) -0.0014(4) -0.0058(4) S1 0.0177(5) 0.0225(6) 0.0271(6) -0.0036(5) -0.0053(4) -0.0082(4) S2 0.0215(5) 0.0182(6) 0.0247(6) 0.0022(5) 0.0005(5) -0.0032(4) B1 0.012(2) 0.016(2) 0.020(3) -0.0028(19) -0.0013(18) -0.0029(17) C1 0.021(2) 0.023(2) 0.019(2) -0.0013(18) -0.0035(18) -0.0117(18) C2 0.025(2) 0.024(3) 0.028(3) -0.007(2) -0.003(2) -0.0051(19) C3 0.031(3) 0.018(2) 0.034(3) -0.012(2) -0.004(2) -0.009(2) C4 0.033(3) 0.034(3) 0.032(3) 0.001(2) -0.009(2) -0.023(2) C5 0.020(2) 0.021(2) 0.021(2) -0.0004(18) -0.0018(18) -0.0112(18) C6 0.014(2) 0.027(3) 0.023(2) -0.005(2) -0.0007(18) -0.0050(18) C7 0.019(2) 0.028(3) 0.021(2) -0.002(2) -0.0017(18) -0.0095(19) C8 0.029(3) 0.026(3) 0.031(3) 0.011(2) -0.001(2) -0.007(2) C9 0.018(2) 0.019(2) 0.024(2) -0.0027(19) -0.0027(18) -0.0023(17) C10 0.018(2) 0.033(3) 0.020(2) 0.000(2) -0.0064(18) -0.0048(19) C11 0.015(2) 0.030(3) 0.019(2) -0.0051(19) -0.0036(17) -0.0075(18) C12 0.028(2) 0.025(3) 0.034(3) 0.004(2) -0.008(2) -0.010(2) C13 0.024(2) 0.041(3) 0.027(3) 0.002(2) -0.008(2) -0.016(2) C14 0.023(2) 0.023(2) 0.027(3) -0.006(2) 0.003(2) -0.0048(19) C15 0.016(2) 0.021(2) 0.025(3) -0.0044(19) -0.0022(18) -0.0036(17) C16 0.014(2) 0.019(2) 0.035(3) -0.003(2) -0.0007(19) -0.0017(17) C17 0.024(2) 0.022(2) 0.042(3) -0.008(2) -0.011(2) -0.0060(19) C18 0.029(3) 0.034(3) 0.038(3) -0.015(2) -0.011(2) -0.006(2) C19 0.040(3) 0.042(3) 0.026(3) -0.004(2) -0.007(2) -0.019(3) C20 0.024(2) 0.028(3) 0.027(3) -0.005(2) -0.006(2) -0.012(2) C21 0.017(2) 0.022(2) 0.018(2) -0.0046(18) 0.0001(17) -0.0078(17) C22 0.023(2) 0.021(2) 0.027(3) -0.003(2) -0.0044(19) -0.0055(19) C23 0.021(2) 0.026(3) 0.034(3) -0.004(2) -0.002(2) -0.009(2) C24 0.027(2) 0.026(3) 0.031(3) -0.001(2) 0.000(2) -0.016(2) C25 0.025(2) 0.025(3) 0.028(3) 0.002(2) -0.002(2) -0.012(2) C26 0.022(2) 0.023(2) 0.019(2) 0.0001(19) -0.0010(18) -0.0088(18) C27 0.0122(19) 0.022(2) 0.028(3) -0.001(2) -0.0019(18) -0.0048(17) C28 0.023(2) 0.023(2) 0.029(3) -0.001(2) -0.002(2) -0.0056(19) C29 0.025(2) 0.021(3) 0.039(3) 0.004(2) -0.003(2) -0.003(2) C30 0.023(2) 0.028(3) 0.041(3) 0.014(2) -0.012(2) -0.003(2) C31 0.035(3) 0.038(3) 0.035(3) 0.008(2) -0.016(2) -0.012(2) C32 0.028(2) 0.025(3) 0.029(3) 0.003(2) -0.006(2) -0.010(2) C33 0.067(5) 0.060(5) 0.048(4) 0.013(4) -0.008(4) -0.020(4) Cl1 0.1129(19) 0.0953(18) 0.0757(16) 0.0148(14) -0.0170(14) -0.0630(16) Cl2 0.0523(10) 0.0713(13) 0.0523(11) 0.0141(9) -0.0118(8) 0.0003(9) C34 0.072(5) 0.038(4) 0.080(6) -0.001(4) 0.022(4) -0.020(4) Cl3 0.0516(9) 0.0473(9) 0.0484(10) 0.0045(8) -0.0044(8) -0.0096(7) Cl4 0.0513(10) 0.0774(14) 0.0635(13) 0.0054(11) -0.0119(9) 0.0024(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C14 1.830(5) . yes Ir1 B1 2.220(5) . yes Ir1 P1 2.4075(11) . yes Ir1 S1 2.4192(11) . yes Ir1 S2 2.4500(13) . yes Ir1 H1 1.481(19) . ? N1 C1 1.340(6) . ? N1 C2 1.400(6) . ? N1 B1 1.566(6) . yes N2 C1 1.349(6) . ? N2 C3 1.392(6) . ? N2 C4 1.457(6) . ? N3 C5 1.340(6) . ? N3 C6 1.392(6) . ? N3 B1 1.566(6) . yes N4 C5 1.348(6) . ? N4 C7 1.388(6) . ? N4 C8 1.466(6) . ? N5 C9 1.362(6) . ? N5 N6 1.381(5) . ? N5 B1 1.534(6) . yes N6 C11 1.321(6) . ? O1 C14 1.156(6) . ? P1 C15 1.826(5) . ? P1 C27 1.831(5) . ? P1 C21 1.834(5) . ? S1 C1 1.712(5) . ? S2 C5 1.710(5) . ? C2 C3 1.341(7) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 C7 1.348(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.379(7) . ? C9 C12 1.504(7) . ? C10 C11 1.396(7) . ? C10 H10 0.9500 . ? C11 C13 1.503(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C15 C20 1.380(7) . ? C15 C16 1.415(7) . ? C16 C17 1.370(7) . ? C16 H16 0.9500 . ? C17 C18 1.384(8) . ? C17 H17 0.9500 . ? C18 C19 1.385(8) . ? C18 H18 0.9500 . ? C19 C20 1.394(7) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.392(7) . ? C21 C22 1.395(6) . ? C22 C23 1.387(7) . ? C22 H22 0.9500 . ? C23 C24 1.381(7) . ? C23 H23 0.9500 . ? C24 C25 1.395(7) . ? C24 H24 0.9500 . ? C25 C26 1.386(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.394(7) . ? C27 C32 1.397(7) . ? C28 C29 1.400(7) . ? C28 H28 0.9500 . ? C29 C30 1.370(8) . ? C29 H29 0.9500 . ? C30 C31 1.391(8) . ? C30 H30 0.9500 . ? C31 C32 1.387(8) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 Cl1 1.762(9) . ? C33 Cl2 1.772(8) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 Cl3 1.724(7) . ? C34 Cl4 1.741(8) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? 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 C14 Ir1 B1 85.96(19) . . yes C14 Ir1 P1 98.63(15) . . yes B1 Ir1 P1 175.26(13) . . yes C14 Ir1 S1 168.29(16) . . yes B1 Ir1 S1 85.26(13) . . yes P1 Ir1 S1 90.03(4) . . yes C14 Ir1 S2 94.64(17) . . yes B1 Ir1 S2 86.30(14) . . yes P1 Ir1 S2 94.50(4) . . yes S1 Ir1 S2 92.51(4) . . yes C14 Ir1 H1 84.8(19) . . ? B1 Ir1 H1 87.5(19) . . ? P1 Ir1 H1 91.7(19) . . ? S1 Ir1 H1 87.1(19) . . ? S2 Ir1 H1 173.8(19) . . ? C1 N1 C2 107.5(4) . . ? C1 N1 B1 122.0(4) . . ? C2 N1 B1 129.2(4) . . ? C1 N2 C3 108.2(4) . . ? C1 N2 C4 125.6(4) . . ? C3 N2 C4 126.2(4) . . ? C5 N3 C6 108.0(4) . . ? C5 N3 B1 123.6(4) . . ? C6 N3 B1 128.0(4) . . ? C5 N4 C7 108.8(4) . . ? C5 N4 C8 124.3(4) . . ? C7 N4 C8 126.9(4) . . ? C9 N5 N6 110.1(4) . . ? C9 N5 B1 129.7(4) . . ? N6 N5 B1 119.3(4) . . ? C11 N6 N5 106.0(4) . . ? C15 P1 C27 103.8(2) . . ? C15 P1 C21 103.1(2) . . ? C27 P1 C21 102.3(2) . . ? C15 P1 Ir1 113.33(15) . . ? C27 P1 Ir1 116.73(15) . . ? C21 P1 Ir1 115.85(15) . . ? C1 S1 Ir1 97.72(15) . . ? C5 S2 Ir1 96.81(17) . . ? N5 B1 N3 107.6(3) . . ? N5 B1 N1 108.6(4) . . ? N3 B1 N1 105.5(4) . . ? N5 B1 Ir1 119.4(3) . . yes N3 B1 Ir1 107.7(3) . . ? N1 B1 Ir1 107.3(3) . . ? N1 C1 N2 108.9(4) . . ? N1 C1 S1 124.1(3) . . ? N2 C1 S1 126.9(3) . . ? C3 C2 N1 108.1(4) . . ? C3 C2 H2 125.9 . . ? N1 C2 H2 125.9 . . ? C2 C3 N2 107.2(4) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N4 108.4(4) . . ? N3 C5 S2 125.3(4) . . ? N4 C5 S2 126.2(4) . . ? C7 C6 N3 108.1(4) . . ? C7 C6 H6 126.0 . . ? N3 C6 H6 126.0 . . ? C6 C7 N4 106.8(4) . . ? C6 C7 H7 126.6 . . ? N4 C7 H7 126.6 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 C10 107.0(4) . . ? N5 C9 C12 123.5(4) . . ? C10 C9 C12 129.4(5) . . ? C9 C10 C11 105.7(4) . . ? C9 C10 H10 127.1 . . ? C11 C10 H10 127.1 . . ? N6 C11 C10 111.1(4) . . ? N6 C11 C13 121.0(5) . . ? C10 C11 C13 127.9(5) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 Ir1 176.8(5) . . ? C20 C15 C16 118.4(5) . . ? C20 C15 P1 123.0(4) . . ? C16 C15 P1 118.6(4) . . ? C17 C16 C15 120.8(5) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 119.9(5) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 120.4(5) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C20 119.6(5) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C15 C20 C19 120.8(5) . . ? C15 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C26 C21 C22 118.9(4) . . ? C26 C21 P1 118.5(3) . . ? C22 C21 P1 122.5(4) . . ? C23 C22 C21 120.6(5) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 119.9(5) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.2(5) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 119.5(5) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C21 120.8(4) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C28 C27 C32 118.5(5) . . ? C28 C27 P1 123.5(4) . . ? C32 C27 P1 117.9(4) . . ? C27 C28 C29 120.6(5) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C30 C29 C28 119.6(5) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C31 120.8(5) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C32 C31 C30 119.4(5) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? C31 C32 C27 120.9(5) . . ? C31 C32 H32 119.5 . . ? C27 C32 H32 119.5 . . ? Cl1 C33 Cl2 111.6(4) . . ? Cl1 C33 H33A 109.3 . . ? Cl2 C33 H33A 109.3 . . ? Cl1 C33 H33B 109.3 . . ? Cl2 C33 H33B 109.3 . . ? H33A C33 H33B 108.0 . . ? Cl3 C34 Cl4 113.7(5) . . ? Cl3 C34 H34A 108.8 . . ? Cl4 C34 H34A 108.8 . . ? Cl3 C34 H34B 108.8 . . ? Cl4 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N5 N6 C11 -0.9(5) . . . . ? B1 N5 N6 C11 -170.9(4) . . . . ? C14 Ir1 P1 C15 16.7(3) . . . . ? B1 Ir1 P1 C15 -148.4(18) . . . . ? S1 Ir1 P1 C15 -155.34(18) . . . . ? S2 Ir1 P1 C15 112.15(18) . . . . ? C14 Ir1 P1 C27 -103.7(2) . . . . ? B1 Ir1 P1 C27 91.1(18) . . . . ? S1 Ir1 P1 C27 84.18(18) . . . . ? S2 Ir1 P1 C27 -8.33(18) . . . . ? C14 Ir1 P1 C21 135.7(2) . . . . ? B1 Ir1 P1 C21 -29.4(18) . . . . ? S1 Ir1 P1 C21 -36.38(18) . . . . ? S2 Ir1 P1 C21 -128.89(18) . . . . ? C14 Ir1 S1 C1 30.8(8) . . . . ? B1 Ir1 S1 C1 -10.8(2) . . . . ? P1 Ir1 S1 C1 168.67(17) . . . . ? S2 Ir1 S1 C1 -96.83(17) . . . . ? C14 Ir1 S2 C5 -82.7(2) . . . . ? B1 Ir1 S2 C5 2.9(2) . . . . ? P1 Ir1 S2 C5 178.26(16) . . . . ? S1 Ir1 S2 C5 88.03(16) . . . . ? C9 N5 B1 N3 167.9(4) . . . . ? N6 N5 B1 N3 -24.3(5) . . . . ? C9 N5 B1 N1 54.3(6) . . . . ? N6 N5 B1 N1 -138.0(4) . . . . ? C9 N5 B1 Ir1 -69.1(6) . . . . ? N6 N5 B1 Ir1 98.7(4) . . . . yes C5 N3 B1 N5 134.7(4) . . . . ? C6 N3 B1 N5 -53.3(6) . . . . ? C5 N3 B1 N1 -109.6(4) . . . . ? C6 N3 B1 N1 62.4(5) . . . . ? C5 N3 B1 Ir1 4.8(5) . . . . ? C6 N3 B1 Ir1 176.8(4) . . . . ? C1 N1 B1 N5 -150.6(4) . . . . ? C2 N1 B1 N5 43.7(7) . . . . ? C1 N1 B1 N3 94.3(5) . . . . ? C2 N1 B1 N3 -71.4(6) . . . . ? C1 N1 B1 Ir1 -20.3(5) . . . . ? C2 N1 B1 Ir1 174.0(4) . . . . ? C14 Ir1 B1 N5 -32.1(4) . . . . ? P1 Ir1 B1 N5 133.2(16) . . . . ? S1 Ir1 B1 N5 140.2(3) . . . . ? S2 Ir1 B1 N5 -127.0(3) . . . . ? C14 Ir1 B1 N3 90.9(3) . . . . ? P1 Ir1 B1 N3 -103.9(17) . . . . ? S1 Ir1 B1 N3 -96.9(3) . . . . ? S2 Ir1 B1 N3 -4.1(3) . . . . ? C14 Ir1 B1 N1 -156.0(4) . . . . ? P1 Ir1 B1 N1 9(2) . . . . ? S1 Ir1 B1 N1 16.2(3) . . . . ? S2 Ir1 B1 N1 109.1(3) . . . . ? C2 N1 C1 N2 -1.0(6) . . . . ? B1 N1 C1 N2 -169.4(4) . . . . ? C2 N1 C1 S1 179.7(4) . . . . ? B1 N1 C1 S1 11.3(7) . . . . ? C3 N2 C1 N1 0.9(6) . . . . ? C4 N2 C1 N1 -178.5(5) . . . . ? C3 N2 C1 S1 -179.8(4) . . . . ? C4 N2 C1 S1 0.8(8) . . . . ? Ir1 S1 C1 N1 3.5(4) . . . . ? Ir1 S1 C1 N2 -175.7(4) . . . . ? C1 N1 C2 C3 0.7(6) . . . . ? B1 N1 C2 C3 168.0(5) . . . . ? N1 C2 C3 N2 -0.2(6) . . . . ? C1 N2 C3 C2 -0.4(6) . . . . ? C4 N2 C3 C2 178.9(5) . . . . ? C6 N3 C5 N4 0.9(5) . . . . ? B1 N3 C5 N4 174.2(4) . . . . ? C6 N3 C5 S2 -175.5(3) . . . . ? B1 N3 C5 S2 -2.2(6) . . . . ? C7 N4 C5 N3 -0.8(5) . . . . ? C8 N4 C5 N3 179.9(4) . . . . ? C7 N4 C5 S2 175.6(4) . . . . ? C8 N4 C5 S2 -3.7(7) . . . . ? Ir1 S2 C5 N3 -1.4(4) . . . . ? Ir1 S2 C5 N4 -177.2(4) . . . . ? C5 N3 C6 C7 -0.6(5) . . . . ? B1 N3 C6 C7 -173.6(4) . . . . ? N3 C6 C7 N4 0.1(5) . . . . ? C5 N4 C7 C6 0.4(5) . . . . ? C8 N4 C7 C6 179.7(5) . . . . ? N6 N5 C9 C10 0.6(5) . . . . ? B1 N5 C9 C10 169.2(4) . . . . ? N6 N5 C9 C12 -178.2(4) . . . . ? B1 N5 C9 C12 -9.5(7) . . . . ? N5 C9 C10 C11 -0.1(5) . . . . ? C12 C9 C10 C11 178.6(5) . . . . ? N5 N6 C11 C10 0.8(5) . . . . ? N5 N6 C11 C13 -179.6(4) . . . . ? C9 C10 C11 N6 -0.5(6) . . . . ? C9 C10 C11 C13 180.0(5) . . . . ? B1 Ir1 C14 O1 37(8) . . . . ? P1 Ir1 C14 O1 -142(8) . . . . ? S1 Ir1 C14 O1 -4(9) . . . . ? S2 Ir1 C14 O1 123(8) . . . . ? C27 P1 C15 C20 -117.0(4) . . . . ? C21 P1 C15 C20 -10.6(5) . . . . ? Ir1 P1 C15 C20 115.4(4) . . . . ? C27 P1 C15 C16 65.2(4) . . . . ? C21 P1 C15 C16 171.6(4) . . . . ? Ir1 P1 C15 C16 -62.4(4) . . . . ? C20 C15 C16 C17 1.9(7) . . . . ? P1 C15 C16 C17 179.8(4) . . . . ? C15 C16 C17 C18 -3.5(7) . . . . ? C16 C17 C18 C19 2.2(8) . . . . ? C17 C18 C19 C20 0.5(8) . . . . ? C16 C15 C20 C19 0.8(7) . . . . ? P1 C15 C20 C19 -177.0(4) . . . . ? C18 C19 C20 C15 -2.1(8) . . . . ? C15 P1 C21 C26 86.5(4) . . . . ? C27 P1 C21 C26 -166.0(4) . . . . ? Ir1 P1 C21 C26 -37.9(4) . . . . ? C15 P1 C21 C22 -90.3(4) . . . . ? C27 P1 C21 C22 17.2(5) . . . . ? Ir1 P1 C21 C22 145.3(4) . . . . ? C26 C21 C22 C23 1.4(7) . . . . ? P1 C21 C22 C23 178.3(4) . . . . ? C21 C22 C23 C24 -2.1(8) . . . . ? C22 C23 C24 C25 1.8(8) . . . . ? C23 C24 C25 C26 -0.7(8) . . . . ? C24 C25 C26 C21 0.0(8) . . . . ? C22 C21 C26 C25 -0.3(7) . . . . ? P1 C21 C26 C25 -177.3(4) . . . . ? C15 P1 C27 C28 3.5(4) . . . . ? C21 P1 C27 C28 -103.6(4) . . . . ? Ir1 P1 C27 C28 128.9(4) . . . . ? C15 P1 C27 C32 -177.5(4) . . . . ? C21 P1 C27 C32 75.5(4) . . . . ? Ir1 P1 C27 C32 -52.0(4) . . . . ? C32 C27 C28 C29 1.1(7) . . . . ? P1 C27 C28 C29 -179.8(4) . . . . ? C27 C28 C29 C30 -1.6(8) . . . . ? C28 C29 C30 C31 0.9(8) . . . . ? C29 C30 C31 C32 0.2(8) . . . . ? C30 C31 C32 C27 -0.7(8) . . . . ? C28 C27 C32 C31 0.0(7) . . . . ? P1 C27 C32 C31 -179.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.360 _refine_diff_density_min -1.067 _refine_diff_density_rms 0.148 data_8 _database_code_depnum_ccdc_archive 'CCDC 804003' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H29 B Ir N6 O P S2, C H2 Cl2' _chemical_formula_sum 'C31 H31 B Cl2 Ir N6 O P S2' _chemical_formula_weight 872.62 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.55120(10) _cell_length_b 17.3810(2) _cell_length_c 20.3269(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3374.46(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9413 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 30.494 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 4.322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5140 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'SADABS V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 39403 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 30.55 _reflns_number_total 10267 _reflns_number_gt 9699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex II (Bruker-AXS, 2007)' _computing_cell_refinement 'Apex II (Bruker-AXS, 2007)' _computing_data_reduction ; SAINT v7.34A (Bruker-AXS, 2007) & XPREP v2005/4 (Bruker-AXS, 2005) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(3) _refine_ls_number_reflns 10267 _refine_ls_number_parameters 431 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0231 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_ref 0.0423 _refine_ls_wR_factor_gt 0.0417 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.889 _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 0.816843(9) 0.291112(5) 0.185843(4) 0.01300(2) Uani 1 1 d . . . H1 H 0.921(3) 0.2788(15) 0.1262(13) 0.016 Uiso 1 1 d . . . N1 N 1.0942(2) 0.36674(12) 0.22659(10) 0.0149(4) Uani 1 1 d . . . N2 N 1.2438(2) 0.29163(14) 0.27664(10) 0.0192(4) Uani 1 1 d . . . N3 N 0.8776(2) 0.43894(11) 0.26268(10) 0.0150(4) Uani 1 1 d . . . N4 N 0.7528(2) 0.45965(13) 0.35091(11) 0.0197(5) Uani 1 1 d . . . N5 N 0.9666(2) 0.45301(11) 0.14814(10) 0.0166(4) Uani 1 1 d . . . N6 N 0.8700(3) 0.50909(13) 0.13769(12) 0.0246(5) Uani 1 1 d . . . O1 O 0.6343(2) 0.38970(12) 0.10219(10) 0.0324(5) Uani 1 1 d . . . P1 P 0.68972(8) 0.17436(3) 0.16375(3) 0.01424(11) Uani 1 1 d . . . S1 S 0.99701(7) 0.22170(3) 0.24395(3) 0.01908(13) Uani 1 1 d . . . S2 S 0.69790(7) 0.32192(3) 0.29040(3) 0.01675(12) Uani 1 1 d . . . B1 B 0.9450(3) 0.39370(15) 0.20409(14) 0.0151(5) Uani 1 1 d . . . C1 C 1.1150(2) 0.29524(16) 0.25024(12) 0.0168(5) Uani 1 1 d . . . C2 C 1.2144(3) 0.40881(15) 0.23856(13) 0.0191(5) Uani 1 1 d . . . H2 H 1.2285 0.4613 0.2273 0.023 Uiso 1 1 calc R . . C3 C 1.3083(3) 0.36302(14) 0.26889(13) 0.0222(5) Uani 1 1 d . . . H3 H 1.4002 0.3767 0.2823 0.027 Uiso 1 1 calc R . . C4 C 1.3026(3) 0.22445(14) 0.30893(16) 0.0288(6) Uani 1 1 d . . . H4A H 1.2730 0.2236 0.3551 0.043 Uiso 1 1 calc R . . H4B H 1.4050 0.2267 0.3067 0.043 Uiso 1 1 calc R . . H4C H 1.2695 0.1778 0.2868 0.043 Uiso 1 1 calc R . . C5 C 0.7787(2) 0.40934(13) 0.30188(12) 0.0149(5) Uani 1 1 d . . . C6 C 0.9133(3) 0.51123(14) 0.28766(14) 0.0204(6) Uani 1 1 d . . . H6 H 0.9806 0.5454 0.2695 0.025 Uiso 1 1 calc R . . C7 C 0.8364(3) 0.52396(15) 0.34156(14) 0.0233(6) Uani 1 1 d . . . H7 H 0.8386 0.5687 0.3684 0.028 Uiso 1 1 calc R . . C8 C 0.6557(3) 0.44715(17) 0.40522(14) 0.0290(7) Uani 1 1 d . . . H8A H 0.5594 0.4495 0.3888 0.044 Uiso 1 1 calc R . . H8B H 0.6696 0.4871 0.4386 0.044 Uiso 1 1 calc R . . H8C H 0.6730 0.3965 0.4247 0.044 Uiso 1 1 calc R . . C9 C 1.0647(3) 0.45469(15) 0.10025(13) 0.0219(6) Uani 1 1 d . . . H9 H 1.1421 0.4206 0.0965 0.026 Uiso 1 1 calc R . . C10 C 1.0339(3) 0.51369(15) 0.05818(14) 0.0258(6) Uani 1 1 d . . . H10 H 1.0845 0.5294 0.0203 0.031 Uiso 1 1 calc R . . C11 C 0.9120(3) 0.54529(16) 0.08333(15) 0.0282(7) Uani 1 1 d . . . H11 H 0.8642 0.5876 0.0642 0.034 Uiso 1 1 calc R . . C12 C 0.7030(3) 0.35179(14) 0.13527(13) 0.0204(5) Uani 1 1 d . . . C13 C 0.6217(3) 0.12141(14) 0.23466(12) 0.0154(5) Uani 1 1 d . . . C14 C 0.6925(3) 0.12532(14) 0.29441(12) 0.0186(5) Uani 1 1 d . . . H14 H 0.7762 0.1547 0.2976 0.022 Uiso 1 1 calc R . . C15 C 0.6420(3) 0.08669(15) 0.34963(14) 0.0224(6) Uani 1 1 d . . . H15 H 0.6916 0.0894 0.3901 0.027 Uiso 1 1 calc R . . C16 C 0.5195(3) 0.04436(15) 0.34546(14) 0.0225(6) Uani 1 1 d . . . H16 H 0.4845 0.0184 0.3832 0.027 Uiso 1 1 calc R . . C17 C 0.4481(3) 0.03987(15) 0.28629(14) 0.0225(6) Uani 1 1 d . . . H17 H 0.3643 0.0106 0.2834 0.027 Uiso 1 1 calc R . . C18 C 0.4983(3) 0.07769(14) 0.23154(13) 0.0184(5) Uani 1 1 d . . . H18 H 0.4487 0.0741 0.1911 0.022 Uiso 1 1 calc R . . C19 C 0.5294(3) 0.18961(13) 0.11533(12) 0.0168(5) Uani 1 1 d . . . C20 C 0.4310(3) 0.24114(16) 0.13866(14) 0.0233(6) Uani 1 1 d . . . H20 H 0.4500 0.2697 0.1775 0.028 Uiso 1 1 calc R . . C21 C 0.3048(3) 0.25175(17) 0.10595(15) 0.0291(6) Uani 1 1 d . . . H21 H 0.2374 0.2868 0.1228 0.035 Uiso 1 1 calc R . . C22 C 0.2772(3) 0.21124(19) 0.04878(14) 0.0290(6) Uani 1 1 d . . . H22 H 0.1911 0.2186 0.0262 0.035 Uiso 1 1 calc R . . C23 C 0.3752(3) 0.16016(17) 0.02466(15) 0.0276(6) Uani 1 1 d . . . H23 H 0.3562 0.1323 -0.0146 0.033 Uiso 1 1 calc R . . C24 C 0.5021(3) 0.14910(15) 0.05752(14) 0.0222(6) Uani 1 1 d . . . H24 H 0.5695 0.1141 0.0405 0.027 Uiso 1 1 calc R . . C25 C 0.7801(3) 0.10044(14) 0.11552(12) 0.0164(5) Uani 1 1 d . . . C26 C 0.7523(3) 0.02284(15) 0.12384(14) 0.0215(6) Uani 1 1 d . . . H26 H 0.6906 0.0066 0.1578 0.026 Uiso 1 1 calc R . . C27 C 0.8138(4) -0.03141(15) 0.08284(14) 0.0281(6) Uani 1 1 d . . . H27 H 0.7955 -0.0846 0.0894 0.034 Uiso 1 1 calc R . . C28 C 0.9011(3) -0.00840(18) 0.03279(15) 0.0317(7) Uani 1 1 d . . . H28 H 0.9408 -0.0455 0.0040 0.038 Uiso 1 1 calc R . . C29 C 0.9310(4) 0.06902(17) 0.02447(16) 0.0333(7) Uani 1 1 d . . . H29 H 0.9926 0.0849 -0.0096 0.040 Uiso 1 1 calc R . . C30 C 0.8714(3) 0.12294(16) 0.06559(14) 0.0261(6) Uani 1 1 d . . . H30 H 0.8928 0.1759 0.0599 0.031 Uiso 1 1 calc R . . C31A C 0.8978(4) 0.22920(18) 0.42563(17) 0.0367(8) Uani 0.5592(19) 1 d P A 1 H31A H 0.9450 0.1896 0.3985 0.044 Uiso 0.5592(19) 1 calc PR A 1 H31B H 0.8000 0.2341 0.4101 0.044 Uiso 0.5592(19) 1 calc PR A 1 Cl1A Cl 0.98414(16) 0.31727(8) 0.41674(8) 0.0372(4) Uani 0.5592(19) 1 d P A 1 Cl2A Cl 0.8990(3) 0.20044(11) 0.50996(9) 0.0656(7) Uani 0.5592(19) 1 d P A 1 C31B C 0.8978(4) 0.22920(18) 0.42563(17) 0.0367(8) Uani 0.4408(19) 1 d P . 2 H31C H 0.8663 0.2637 0.3898 0.044 Uiso 0.4408(19) 1 calc PR A 2 H31D H 0.9103 0.1770 0.4069 0.044 Uiso 0.4408(19) 1 calc PR A 2 Cl3B Cl 1.0630(3) 0.26324(13) 0.45785(13) 0.0584(7) Uani 0.4408(19) 1 d P . 2 Cl4B Cl 0.7733(2) 0.22637(13) 0.48589(12) 0.0530(7) Uani 0.4408(19) 1 d P . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01352(4) 0.01276(4) 0.01272(4) 0.00040(4) 0.00019(4) -0.00084(4) N1 0.0129(10) 0.0153(10) 0.0164(11) -0.0014(8) -0.0004(8) 0.0017(8) N2 0.0159(10) 0.0196(10) 0.0219(11) -0.0009(11) -0.0012(8) 0.0043(10) N3 0.0142(10) 0.0139(9) 0.0170(11) -0.0008(8) -0.0022(8) 0.0006(8) N4 0.0221(12) 0.0209(11) 0.0161(11) -0.0027(9) 0.0007(9) 0.0039(9) N5 0.0186(11) 0.0148(10) 0.0163(11) 0.0012(8) 0.0015(9) -0.0021(8) N6 0.0280(13) 0.0200(11) 0.0258(13) 0.0059(10) 0.0037(10) 0.0044(10) O1 0.0410(13) 0.0289(11) 0.0274(12) 0.0027(9) -0.0140(10) 0.0069(9) P1 0.0157(3) 0.0142(3) 0.0128(3) -0.0002(2) 0.0005(3) -0.0013(3) S1 0.0150(3) 0.0151(3) 0.0272(3) 0.0035(2) -0.0007(2) 0.0006(2) S2 0.0151(3) 0.0182(3) 0.0169(3) 0.0009(2) 0.0029(3) -0.0008(2) B1 0.0131(12) 0.0147(12) 0.0176(14) 0.0016(10) 0.0017(10) 0.0011(10) C1 0.0162(11) 0.0166(11) 0.0176(12) 0.0011(11) 0.0016(9) 0.0014(10) C2 0.0146(13) 0.0177(12) 0.0251(14) -0.0033(10) 0.0008(10) -0.0028(9) C3 0.0147(12) 0.0228(12) 0.0290(14) -0.0071(10) -0.0002(12) -0.0004(11) C4 0.0200(13) 0.0264(14) 0.0398(17) 0.0071(13) -0.0070(15) 0.0073(11) C5 0.0158(11) 0.0163(11) 0.0127(13) -0.0011(9) 0.0003(9) 0.0047(8) C6 0.0190(13) 0.0151(12) 0.0272(14) -0.0049(11) -0.0028(11) -0.0022(10) C7 0.0227(15) 0.0207(12) 0.0264(14) -0.0074(11) -0.0059(12) 0.0001(11) C8 0.0350(19) 0.0349(15) 0.0172(14) -0.0023(11) 0.0096(12) 0.0043(13) C9 0.0242(14) 0.0220(13) 0.0194(14) -0.0014(11) 0.0026(11) -0.0031(11) C10 0.0340(16) 0.0262(14) 0.0173(14) 0.0007(11) 0.0050(12) -0.0116(12) C11 0.0395(18) 0.0200(13) 0.0252(16) 0.0055(12) -0.0031(13) -0.0023(12) C12 0.0258(15) 0.0178(11) 0.0174(13) -0.0032(10) -0.0010(11) -0.0029(11) C13 0.0171(12) 0.0126(11) 0.0167(13) -0.0006(9) 0.0018(10) -0.0012(9) C14 0.0209(12) 0.0183(11) 0.0165(12) 0.0017(9) -0.0019(11) -0.0048(11) C15 0.0265(15) 0.0239(13) 0.0169(13) 0.0035(11) -0.0033(11) -0.0038(11) C16 0.0261(15) 0.0225(13) 0.0189(14) 0.0050(11) 0.0047(11) -0.0050(11) C17 0.0211(13) 0.0208(13) 0.0255(14) -0.0006(11) 0.0026(12) -0.0070(11) C18 0.0197(13) 0.0185(12) 0.0170(13) -0.0010(10) -0.0017(10) -0.0035(10) C19 0.0202(13) 0.0165(12) 0.0135(12) 0.0037(9) -0.0007(10) -0.0029(9) C20 0.0230(14) 0.0284(14) 0.0186(14) -0.0016(11) 0.0004(11) 0.0016(11) C21 0.0240(15) 0.0331(15) 0.0301(16) 0.0050(12) 0.0032(14) 0.0065(14) C22 0.0227(13) 0.0356(15) 0.0287(15) 0.0107(15) -0.0097(11) -0.0013(13) C23 0.0325(16) 0.0294(15) 0.0210(15) -0.0015(12) -0.0107(13) -0.0007(12) C24 0.0270(14) 0.0209(13) 0.0186(14) 0.0008(11) -0.0057(12) 0.0021(11) C25 0.0187(13) 0.0186(11) 0.0120(12) -0.0008(9) 0.0005(9) -0.0017(9) C26 0.0244(14) 0.0216(13) 0.0184(14) -0.0011(11) 0.0024(11) -0.0015(11) C27 0.0365(16) 0.0185(12) 0.0292(15) -0.0056(11) 0.0055(15) -0.0016(14) C28 0.0402(18) 0.0300(16) 0.0249(16) -0.0136(13) 0.0117(14) 0.0007(13) C29 0.0414(19) 0.0335(16) 0.0250(16) -0.0009(13) 0.0158(14) -0.0028(14) C30 0.0347(16) 0.0222(13) 0.0213(15) -0.0007(12) 0.0101(12) -0.0020(12) C31A 0.043(2) 0.0327(17) 0.0339(18) 0.0029(13) -0.0017(15) -0.0016(14) Cl1A 0.0398(8) 0.0301(7) 0.0415(9) 0.0090(6) -0.0183(7) -0.0126(6) Cl2A 0.1044(19) 0.0464(11) 0.0459(10) 0.0045(9) 0.0234(11) -0.0029(11) C31B 0.043(2) 0.0327(17) 0.0339(18) 0.0029(13) -0.0017(15) -0.0016(14) Cl3B 0.0483(13) 0.0458(12) 0.0810(19) -0.0083(11) -0.0037(12) -0.0124(10) Cl4B 0.0539(14) 0.0592(15) 0.0460(13) -0.0075(10) 0.0256(10) -0.0154(10) _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 1.830(3) . yes Ir1 B1 2.195(3) . yes Ir1 P1 2.4071(6) . yes Ir1 S1 2.4107(6) . yes Ir1 S2 2.4687(6) . yes Ir1 H1 1.58(3) . ? N1 C1 1.347(3) . ? N1 C2 1.383(3) . ? N1 B1 1.568(3) . yes N2 C1 1.344(3) . ? N2 C3 1.394(3) . ? N2 C4 1.452(3) . ? N3 C5 1.339(3) . ? N3 C6 1.397(3) . ? N3 B1 1.566(3) . yes N4 C5 1.349(3) . ? N4 C7 1.387(3) . ? N4 C8 1.458(3) . ? N5 C9 1.351(3) . ? N5 N6 1.359(3) . ? N5 B1 1.549(3) . yes N6 C11 1.333(4) . ? O1 C12 1.148(3) . ? P1 C13 1.829(3) . ? P1 C25 1.832(3) . ? P1 C19 1.839(3) . ? S1 C1 1.709(3) . ? S2 C5 1.720(2) . ? C2 C3 1.348(4) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 C7 1.338(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.368(4) . ? C9 H9 0.9500 . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C13 C14 1.392(3) . ? C13 C18 1.404(3) . ? C14 C15 1.394(4) . ? C14 H14 0.9500 . ? C15 C16 1.385(4) . ? C15 H15 0.9500 . ? C16 C17 1.385(4) . ? C16 H16 0.9500 . ? C17 C18 1.379(4) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.382(4) . ? C19 C24 1.395(4) . ? C20 C21 1.389(4) . ? C20 H20 0.9500 . ? C21 C22 1.384(4) . ? C21 H21 0.9500 . ? C22 C23 1.380(4) . ? C22 H22 0.9500 . ? C23 C24 1.397(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.385(3) . ? C25 C30 1.394(4) . ? C26 C27 1.389(4) . ? C26 H26 0.9500 . ? C27 C28 1.375(4) . ? C27 H27 0.9500 . ? C28 C29 1.386(4) . ? C28 H28 0.9500 . ? C29 C30 1.379(4) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31A Cl1A 1.748(3) . ? C31A Cl2A 1.786(4) . ? C31A H31A 0.9900 . ? C31A H31B 0.9900 . ? Cl3B Cl4B 2.319(3) 4_556 ? Cl4B Cl3B 2.319(3) 4_456 ? 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 B1 87.60(11) . . yes C12 Ir1 P1 94.67(8) . . yes B1 Ir1 P1 176.33(8) . . yes C12 Ir1 S1 170.89(9) . . yes B1 Ir1 S1 85.73(8) . . yes P1 Ir1 S1 91.70(2) . . yes C12 Ir1 S2 94.89(8) . . yes B1 Ir1 S2 86.27(8) . . yes P1 Ir1 S2 96.39(2) . . yes S1 Ir1 S2 90.87(2) . . yes C12 Ir1 H1 91.1(10) . . ? B1 Ir1 H1 83.6(9) . . ? P1 Ir1 H1 93.4(9) . . ? S1 Ir1 H1 82.0(9) . . ? S2 Ir1 H1 168.0(9) . . ? C1 N1 C2 107.6(2) . . ? C1 N1 B1 120.9(2) . . ? C2 N1 B1 130.4(2) . . ? C1 N2 C3 108.5(2) . . ? C1 N2 C4 124.9(2) . . ? C3 N2 C4 126.6(2) . . ? C5 N3 C6 107.5(2) . . ? C5 N3 B1 123.4(2) . . ? C6 N3 B1 128.9(2) . . ? C5 N4 C7 108.4(2) . . ? C5 N4 C8 125.4(2) . . ? C7 N4 C8 126.2(2) . . ? C9 N5 N6 110.0(2) . . ? C9 N5 B1 129.5(2) . . ? N6 N5 B1 120.1(2) . . ? C11 N6 N5 105.3(2) . . ? C13 P1 C25 103.66(11) . . ? C13 P1 C19 101.45(12) . . ? C25 P1 C19 101.96(12) . . ? C13 P1 Ir1 117.14(8) . . ? C25 P1 Ir1 116.95(8) . . ? C19 P1 Ir1 113.47(8) . . ? C1 S1 Ir1 97.65(9) . . ? C5 S2 Ir1 95.85(8) . . ? N5 B1 N3 106.21(19) . . ? N5 B1 N1 107.0(2) . . ? N3 B1 N1 107.6(2) . . ? N5 B1 Ir1 119.41(18) . . yes N3 B1 Ir1 107.89(16) . . ? N1 B1 Ir1 108.26(16) . . ? N2 C1 N1 108.7(2) . . ? N2 C1 S1 126.8(2) . . ? N1 C1 S1 124.46(19) . . ? C3 C2 N1 108.7(2) . . ? C3 C2 H2 125.6 . . ? N1 C2 H2 125.6 . . ? C2 C3 N2 106.5(2) . . ? C2 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N4 108.7(2) . . ? N3 C5 S2 125.13(18) . . ? N4 C5 S2 126.20(19) . . ? C7 C6 N3 108.2(2) . . ? C7 C6 H6 125.9 . . ? N3 C6 H6 125.9 . . ? C6 C7 N4 107.2(2) . . ? C6 C7 H7 126.4 . . ? N4 C7 H7 126.4 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 C10 108.5(2) . . ? N5 C9 H9 125.8 . . ? C10 C9 H9 125.8 . . ? C9 C10 C11 104.3(3) . . ? C9 C10 H10 127.8 . . ? C11 C10 H10 127.8 . . ? N6 C11 C10 111.8(3) . . ? N6 C11 H11 124.1 . . ? C10 C11 H11 124.1 . . ? O1 C12 Ir1 178.1(3) . . ? C14 C13 C18 118.3(2) . . ? C14 C13 P1 119.38(19) . . ? C18 C13 P1 122.3(2) . . ? C13 C14 C15 120.7(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.9(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C17 C16 C15 120.0(3) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C18 C17 C16 120.2(2) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C13 120.9(2) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? C20 C19 C24 119.3(3) . . ? C20 C19 P1 118.4(2) . . ? C24 C19 P1 122.3(2) . . ? C19 C20 C21 120.8(3) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 120.0(3) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C23 C22 C21 119.7(3) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 120.5(3) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C19 C24 C23 119.7(3) . . ? C19 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C26 C25 C30 118.8(2) . . ? C26 C25 P1 121.8(2) . . ? C30 C25 P1 119.18(19) . . ? C25 C26 C27 120.4(3) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C28 C27 C26 120.2(2) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C29 119.8(3) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C30 C29 C28 120.1(3) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C25 120.6(3) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? Cl1A C31A Cl2A 110.0(2) . . ? Cl1A C31A H31A 109.7 . . ? Cl2A C31A H31A 109.7 . . ? Cl1A C31A H31B 109.7 . . ? Cl2A C31A H31B 109.7 . . ? H31A C31A H31B 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N5 N6 C11 -0.8(3) . . . . ? B1 N5 N6 C11 -174.4(2) . . . . ? C12 Ir1 P1 C13 -123.10(13) . . . . ? B1 Ir1 P1 C13 108.8(12) . . . . ? S1 Ir1 P1 C13 63.43(10) . . . . ? S2 Ir1 P1 C13 -27.64(10) . . . . ? C12 Ir1 P1 C25 112.96(13) . . . . ? B1 Ir1 P1 C25 -15.1(12) . . . . ? S1 Ir1 P1 C25 -60.51(9) . . . . ? S2 Ir1 P1 C25 -151.58(9) . . . . ? C12 Ir1 P1 C19 -5.34(12) . . . . ? B1 Ir1 P1 C19 -133.4(12) . . . . ? S1 Ir1 P1 C19 -178.81(9) . . . . ? S2 Ir1 P1 C19 90.12(9) . . . . ? C12 Ir1 S1 C1 35.0(5) . . . . ? B1 Ir1 S1 C1 -8.13(11) . . . . ? P1 Ir1 S1 C1 169.25(9) . . . . ? S2 Ir1 S1 C1 -94.33(9) . . . . ? C12 Ir1 S2 C5 -79.83(11) . . . . ? B1 Ir1 S2 C5 7.44(11) . . . . ? P1 Ir1 S2 C5 -175.10(8) . . . . ? S1 Ir1 S2 C5 93.10(8) . . . . ? C9 N5 B1 N3 150.4(2) . . . . ? N6 N5 B1 N3 -37.3(3) . . . . ? C9 N5 B1 N1 35.8(3) . . . . ? N6 N5 B1 N1 -152.0(2) . . . . ? C9 N5 B1 Ir1 -87.5(3) . . . . ? N6 N5 B1 Ir1 84.7(3) . . . . yes C5 N3 B1 N5 142.2(2) . . . . ? C6 N3 B1 N5 -43.8(3) . . . . ? C5 N3 B1 N1 -103.6(3) . . . . ? C6 N3 B1 N1 70.5(3) . . . . ? C5 N3 B1 Ir1 13.0(3) . . . . ? C6 N3 B1 Ir1 -173.0(2) . . . . ? C1 N1 B1 N5 -149.4(2) . . . . ? C2 N1 B1 N5 44.2(3) . . . . ? C1 N1 B1 N3 96.8(3) . . . . ? C2 N1 B1 N3 -69.6(3) . . . . ? C1 N1 B1 Ir1 -19.5(3) . . . . ? C2 N1 B1 Ir1 174.1(2) . . . . ? C12 Ir1 B1 N5 -36.9(2) . . . . ? P1 Ir1 B1 N5 91.4(12) . . . . ? S1 Ir1 B1 N5 136.90(19) . . . . ? S2 Ir1 B1 N5 -131.94(19) . . . . ? C12 Ir1 B1 N3 84.36(18) . . . . ? P1 Ir1 B1 N3 -147.4(11) . . . . ? S1 Ir1 B1 N3 -101.86(16) . . . . ? S2 Ir1 B1 N3 -10.70(15) . . . . ? C12 Ir1 B1 N1 -159.50(18) . . . . ? P1 Ir1 B1 N1 -31.2(13) . . . . ? S1 Ir1 B1 N1 14.28(15) . . . . ? S2 Ir1 B1 N1 105.44(16) . . . . ? C3 N2 C1 N1 -0.7(3) . . . . ? C4 N2 C1 N1 178.0(2) . . . . ? C3 N2 C1 S1 176.9(2) . . . . ? C4 N2 C1 S1 -4.4(4) . . . . ? C2 N1 C1 N2 0.2(3) . . . . ? B1 N1 C1 N2 -169.0(2) . . . . ? C2 N1 C1 S1 -177.52(19) . . . . ? B1 N1 C1 S1 13.3(3) . . . . ? Ir1 S1 C1 N2 -177.3(2) . . . . ? Ir1 S1 C1 N1 0.0(2) . . . . ? C1 N1 C2 C3 0.4(3) . . . . ? B1 N1 C2 C3 168.2(2) . . . . ? N1 C2 C3 N2 -0.9(3) . . . . ? C1 N2 C3 C2 1.0(3) . . . . ? C4 N2 C3 C2 -177.7(2) . . . . ? C6 N3 C5 N4 -1.0(3) . . . . ? B1 N3 C5 N4 174.1(2) . . . . ? C6 N3 C5 S2 178.43(19) . . . . ? B1 N3 C5 S2 -6.4(3) . . . . ? C7 N4 C5 N3 1.2(3) . . . . ? C8 N4 C5 N3 -177.4(2) . . . . ? C7 N4 C5 S2 -178.19(19) . . . . ? C8 N4 C5 S2 3.2(4) . . . . ? Ir1 S2 C5 N3 -3.1(2) . . . . ? Ir1 S2 C5 N4 176.2(2) . . . . ? C5 N3 C6 C7 0.4(3) . . . . ? B1 N3 C6 C7 -174.4(2) . . . . ? N3 C6 C7 N4 0.4(3) . . . . ? C5 N4 C7 C6 -1.0(3) . . . . ? C8 N4 C7 C6 177.6(3) . . . . ? N6 N5 C9 C10 1.1(3) . . . . ? B1 N5 C9 C10 174.0(2) . . . . ? N5 C9 C10 C11 -1.0(3) . . . . ? N5 N6 C11 C10 0.2(3) . . . . ? C9 C10 C11 N6 0.5(3) . . . . ? B1 Ir1 C12 O1 78(7) . . . . ? P1 Ir1 C12 O1 -99(7) . . . . ? S1 Ir1 C12 O1 35(8) . . . . ? S2 Ir1 C12 O1 164(7) . . . . ? C25 P1 C13 C14 100.6(2) . . . . ? C19 P1 C13 C14 -153.9(2) . . . . ? Ir1 P1 C13 C14 -29.8(2) . . . . ? C25 P1 C13 C18 -80.6(2) . . . . ? C19 P1 C13 C18 24.9(2) . . . . ? Ir1 P1 C13 C18 148.98(18) . . . . ? C18 C13 C14 C15 0.1(4) . . . . ? P1 C13 C14 C15 178.9(2) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C14 C15 C16 C17 0.6(4) . . . . ? C15 C16 C17 C18 -0.3(4) . . . . ? C16 C17 C18 C13 -0.2(4) . . . . ? C14 C13 C18 C17 0.3(4) . . . . ? P1 C13 C18 C17 -178.5(2) . . . . ? C13 P1 C19 C20 71.0(2) . . . . ? C25 P1 C19 C20 177.8(2) . . . . ? Ir1 P1 C19 C20 -55.5(2) . . . . ? C13 P1 C19 C24 -106.7(2) . . . . ? C25 P1 C19 C24 0.1(2) . . . . ? Ir1 P1 C19 C24 126.80(19) . . . . ? C24 C19 C20 C21 1.3(4) . . . . ? P1 C19 C20 C21 -176.5(2) . . . . ? C19 C20 C21 C22 -0.9(4) . . . . ? C20 C21 C22 C23 0.3(4) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? C20 C19 C24 C23 -1.0(4) . . . . ? P1 C19 C24 C23 176.6(2) . . . . ? C22 C23 C24 C19 0.4(4) . . . . ? C13 P1 C25 C26 19.5(3) . . . . ? C19 P1 C25 C26 -85.6(2) . . . . ? Ir1 P1 C25 C26 150.0(2) . . . . ? C13 P1 C25 C30 -165.6(2) . . . . ? C19 P1 C25 C30 89.3(2) . . . . ? Ir1 P1 C25 C30 -35.0(2) . . . . ? C30 C25 C26 C27 -0.3(4) . . . . ? P1 C25 C26 C27 174.6(2) . . . . ? C25 C26 C27 C28 -1.2(5) . . . . ? C26 C27 C28 C29 1.9(5) . . . . ? C27 C28 C29 C30 -1.1(5) . . . . ? C28 C29 C30 C25 -0.4(5) . . . . ? C26 C25 C30 C29 1.1(4) . . . . ? P1 C25 C30 C29 -173.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.071 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.083 data_11 _database_code_depnum_ccdc_archive 'CCDC 804004' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H40 B Cl Ir2 N6 S3, 2(C H2 Cl2)' _chemical_formula_sum 'C30 H44 B Cl5 Ir2 N6 S3' _chemical_formula_weight 1157.35 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8535(18) _cell_length_b 14.237(3) _cell_length_c 14.797(3) _cell_angle_alpha 113.731(7) _cell_angle_beta 91.748(7) _cell_angle_gamma 108.989(7) _cell_volume 1944.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 31012 _cell_measurement_theta_min 3.027 _cell_measurement_theta_max 29.46 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.977 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 7.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6298 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_process_details 'SADABS - Bruker 2007' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-AXS Kappa' _diffrn_measurement_method '\w & \f scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 79391 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 29.70 _reflns_number_total 10673 _reflns_number_gt 8955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex II (Bruker-AXS, 2007)' _computing_cell_refinement 'Apex II (Bruker-AXS, 2007)' _computing_data_reduction ; SAINT v7.34A (Bruker-AXS, 2007) & XPREP v2005/4 (Bruker-AXS, 2005) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+5.4257P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10673 _refine_ls_number_parameters 430 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0575 _refine_ls_wR_factor_gt 0.0539 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.643307(12) 0.515369(10) 0.196510(9) 0.01131(4) Uani 1 1 d . . . H1 H 0.625(4) 0.574(3) 0.146(3) 0.014 Uiso 1 1 d . . . Ir2 Ir 0.582792(13) 0.965367(10) 0.280328(9) 0.01288(4) Uani 1 1 d . . . Cl1 Cl 0.72867(9) 1.04731(7) 0.43911(6) 0.01952(17) Uani 1 1 d . . . N1 N 0.5305(3) 0.6871(2) 0.3229(2) 0.0135(6) Uani 1 1 d . . . N2 N 0.3138(3) 0.6346(3) 0.2954(2) 0.0176(6) Uani 1 1 d . . . N3 N 0.6836(3) 0.6551(2) 0.4254(2) 0.0150(6) Uani 1 1 d . . . N4 N 0.6732(3) 0.5695(2) 0.5208(2) 0.0173(6) Uani 1 1 d . . . N5 N 0.7819(3) 0.7768(2) 0.3418(2) 0.0116(5) Uani 1 1 d . . . N6 N 0.9184(3) 0.9161(2) 0.3213(2) 0.0151(6) Uani 1 1 d . . . S1 S 0.41113(9) 0.47271(7) 0.18918(7) 0.01740(17) Uani 1 1 d . . . S2 S 0.64637(9) 0.43872(7) 0.32012(6) 0.01667(17) Uani 1 1 d . . . S3 S 0.67197(8) 0.82766(7) 0.20338(6) 0.01459(16) Uani 1 1 d . . . B1 B 0.6645(4) 0.6674(3) 0.3250(3) 0.0128(7) Uani 1 1 d . . . C1 C 0.4171(3) 0.6020(3) 0.2695(2) 0.0139(7) Uani 1 1 d . . . C2 C 0.4975(4) 0.7756(3) 0.3843(3) 0.0180(7) Uani 1 1 d . . . H2 H 0.5585 0.8466 0.4298 0.022 Uiso 1 1 calc R . . C3 C 0.3634(4) 0.7434(3) 0.3681(3) 0.0202(8) Uani 1 1 d . . . H3 H 0.3133 0.7868 0.4003 0.024 Uiso 1 1 calc R . . C4 C 0.1741(4) 0.5655(3) 0.2537(3) 0.0247(8) Uani 1 1 d . . . H4A H 0.1668 0.4944 0.1999 0.037 Uiso 1 1 calc R . . H4B H 0.1323 0.6026 0.2266 0.037 Uiso 1 1 calc R . . H4C H 0.1293 0.5532 0.3067 0.037 Uiso 1 1 calc R . . C5 C 0.6700(3) 0.5578(3) 0.4251(2) 0.0139(6) Uani 1 1 d . . . C6 C 0.6938(4) 0.7303(3) 0.5247(3) 0.0193(7) Uani 1 1 d . . . H6 H 0.7027 0.8051 0.5467 0.023 Uiso 1 1 calc R . . C7 C 0.6890(4) 0.6782(3) 0.5834(3) 0.0223(8) Uani 1 1 d . . . H7 H 0.6951 0.7094 0.6543 0.027 Uiso 1 1 calc R . . C8 C 0.6681(4) 0.4832(3) 0.5517(3) 0.0244(8) Uani 1 1 d . . . H8A H 0.5999 0.4131 0.5042 0.037 Uiso 1 1 calc R . . H8B H 0.6465 0.5032 0.6191 0.037 Uiso 1 1 calc R . . H8C H 0.7545 0.4754 0.5525 0.037 Uiso 1 1 calc R . . C9 C 0.7921(3) 0.8410(3) 0.2931(2) 0.0135(6) Uani 1 1 d . . . C10 C 0.9054(3) 0.8127(3) 0.4005(2) 0.0145(7) Uani 1 1 d . . . H10 H 0.9273 0.7815 0.4416 0.017 Uiso 1 1 calc R . . C11 C 0.9889(3) 0.8991(3) 0.3889(3) 0.0169(7) Uani 1 1 d . . . H11 H 1.0791 0.9406 0.4211 0.020 Uiso 1 1 calc R . . C12 C 0.9687(4) 1.0045(3) 0.2895(3) 0.0224(8) Uani 1 1 d . . . H12A H 1.0120 0.9802 0.2319 0.034 Uiso 1 1 calc R . . H12B H 1.0329 1.0703 0.3451 0.034 Uiso 1 1 calc R . . H12C H 0.8948 1.0221 0.2703 0.034 Uiso 1 1 calc R . . C13 C 0.8480(3) 0.5255(3) 0.2060(3) 0.0162(7) Uani 1 1 d . . . H13 H 0.9024 0.5720 0.2753 0.019 Uiso 1 1 calc R . . C14 C 0.8296(3) 0.5871(3) 0.1559(3) 0.0161(7) Uani 1 1 d . . . H14 H 0.8737 0.6688 0.1965 0.019 Uiso 1 1 calc R . . C15 C 0.8170(4) 0.5499(3) 0.0432(3) 0.0224(8) Uani 1 1 d . . . H15A H 0.9061 0.5591 0.0255 0.027 Uiso 1 1 calc R . . H15B H 0.7837 0.5982 0.0251 0.027 Uiso 1 1 calc R . . C16 C 0.7239(4) 0.4293(3) -0.0192(3) 0.0225(8) Uani 1 1 d . . . H16A H 0.6888 0.4203 -0.0860 0.027 Uiso 1 1 calc R . . H16B H 0.7755 0.3811 -0.0298 0.027 Uiso 1 1 calc R . . C17 C 0.6078(4) 0.3918(3) 0.0295(3) 0.0193(7) Uani 1 1 d . . . H17 H 0.5185 0.3699 -0.0099 0.023 Uiso 1 1 calc R . . C18 C 0.6105(4) 0.3354(3) 0.0865(3) 0.0170(7) Uani 1 1 d . . . H18 H 0.5230 0.2793 0.0815 0.020 Uiso 1 1 calc R . . C19 C 0.7306(4) 0.3112(3) 0.1111(3) 0.0181(7) Uani 1 1 d . . . H19A H 0.7411 0.2539 0.0494 0.022 Uiso 1 1 calc R . . H19B H 0.7138 0.2807 0.1610 0.022 Uiso 1 1 calc R . . C20 C 0.8617(4) 0.4130(3) 0.1533(3) 0.0200(7) Uani 1 1 d . . . H20A H 0.9178 0.4049 0.2015 0.024 Uiso 1 1 calc R . . H20B H 0.9091 0.4129 0.0972 0.024 Uiso 1 1 calc R . . C21 C 0.5265(4) 1.1065(3) 0.3269(3) 0.0216(8) Uani 1 1 d . . . H21 H 0.5889 1.1742 0.3850 0.026 Uiso 1 1 calc R . . C22 C 0.4418(4) 1.0254(3) 0.3527(3) 0.0202(8) Uani 1 1 d . . . H22 H 0.4553 1.0463 0.4264 0.024 Uiso 1 1 calc R . . C23 C 0.2999(4) 0.9529(3) 0.2979(3) 0.0240(8) Uani 1 1 d . . . H23A H 0.2460 0.9997 0.3101 0.029 Uiso 1 1 calc R . . H23B H 0.2624 0.8992 0.3257 0.029 Uiso 1 1 calc R . . C24 C 0.2899(4) 0.8903(3) 0.1849(3) 0.0253(8) Uani 1 1 d . . . H24A H 0.2681 0.9317 0.1508 0.030 Uiso 1 1 calc R . . H24B H 0.2171 0.8172 0.1595 0.030 Uiso 1 1 calc R . . C25 C 0.4195(4) 0.8743(3) 0.1593(3) 0.0204(8) Uani 1 1 d . . . H25 H 0.4090 0.7955 0.1197 0.025 Uiso 1 1 calc R . . C26 C 0.5203(4) 0.9495(3) 0.1372(3) 0.0221(8) Uani 1 1 d . . . H26 H 0.5675 0.9138 0.0847 0.027 Uiso 1 1 calc R . . C27 C 0.5177(5) 1.0575(4) 0.1417(3) 0.0312(10) Uani 1 1 d . . . H27A H 0.4526 1.0412 0.0840 0.037 Uiso 1 1 calc R . . H27B H 0.6061 1.1016 0.1357 0.037 Uiso 1 1 calc R . . C28 C 0.4810(4) 1.1259(3) 0.2396(3) 0.0274(9) Uani 1 1 d . . . H28A H 0.5226 1.2052 0.2559 0.033 Uiso 1 1 calc R . . H28B H 0.3836 1.1058 0.2300 0.033 Uiso 1 1 calc R . . C29 C 0.1175(5) 0.7106(4) 0.6167(4) 0.0400(11) Uani 1 1 d . . . H29A H 0.1725 0.6700 0.6249 0.048 Uiso 1 1 calc R . . H29B H 0.1777 0.7817 0.6203 0.048 Uiso 1 1 calc R . . Cl2 Cl 0.02647(14) 0.73628(11) 0.71555(10) 0.0470(3) Uani 1 1 d . . . Cl3 Cl 0.01032(12) 0.63224(11) 0.49772(10) 0.0419(3) Uani 1 1 d . . . C30 C 0.8359(8) 0.8234(9) 0.9829(6) 0.101(3) Uani 1 1 d . . . H30A H 0.7662 0.7525 0.9716 0.121 Uiso 1 1 calc R . . H30B H 0.8349 0.8787 1.0499 0.121 Uiso 1 1 calc R . . Cl4 Cl 0.98394(19) 0.80759(19) 0.98991(19) 0.0897(6) Uani 1 1 d . . . Cl5 Cl 0.7901(3) 0.8604(2) 0.8994(2) 0.1181(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01102(6) 0.01155(6) 0.00992(6) 0.00306(5) 0.00187(5) 0.00450(5) Ir2 0.01240(6) 0.01315(6) 0.01161(7) 0.00307(5) 0.00171(5) 0.00594(5) Cl1 0.0189(4) 0.0207(4) 0.0142(4) 0.0018(3) -0.0011(3) 0.0094(4) N1 0.0145(13) 0.0138(13) 0.0137(14) 0.0055(11) 0.0048(11) 0.0074(12) N2 0.0155(14) 0.0234(15) 0.0172(15) 0.0096(13) 0.0065(12) 0.0101(13) N3 0.0149(14) 0.0163(14) 0.0124(14) 0.0049(11) 0.0022(11) 0.0060(12) N4 0.0173(15) 0.0217(15) 0.0167(15) 0.0106(13) 0.0049(12) 0.0086(13) N5 0.0120(13) 0.0127(13) 0.0105(13) 0.0036(11) 0.0029(10) 0.0069(11) N6 0.0129(13) 0.0147(13) 0.0174(15) 0.0069(12) 0.0021(11) 0.0048(12) S1 0.0118(4) 0.0167(4) 0.0174(4) 0.0026(3) 0.0014(3) 0.0040(3) S2 0.0218(4) 0.0149(4) 0.0158(4) 0.0074(3) 0.0055(3) 0.0087(4) S3 0.0159(4) 0.0161(4) 0.0128(4) 0.0052(3) 0.0024(3) 0.0087(3) B1 0.0127(17) 0.0123(17) 0.0129(17) 0.0050(14) 0.0025(14) 0.0044(14) C1 0.0131(15) 0.0189(16) 0.0137(16) 0.0090(13) 0.0044(12) 0.0081(14) C2 0.0214(18) 0.0174(17) 0.0171(17) 0.0071(14) 0.0077(14) 0.0097(15) C3 0.0233(19) 0.0231(18) 0.0206(18) 0.0090(15) 0.0116(15) 0.0164(16) C4 0.0108(16) 0.035(2) 0.026(2) 0.0142(18) 0.0017(14) 0.0050(16) C5 0.0128(15) 0.0174(16) 0.0129(16) 0.0070(13) 0.0034(12) 0.0066(14) C6 0.0221(18) 0.0200(17) 0.0121(16) 0.0036(14) 0.0036(14) 0.0076(15) C7 0.0228(19) 0.0270(19) 0.0144(17) 0.0061(15) 0.0037(14) 0.0098(16) C8 0.027(2) 0.033(2) 0.026(2) 0.0202(18) 0.0108(16) 0.0161(18) C9 0.0130(15) 0.0131(15) 0.0129(16) 0.0036(13) 0.0042(12) 0.0055(13) C10 0.0145(16) 0.0134(15) 0.0131(16) 0.0029(13) -0.0014(13) 0.0061(13) C11 0.0123(16) 0.0169(16) 0.0207(18) 0.0055(14) 0.0010(13) 0.0079(14) C12 0.0187(18) 0.0216(18) 0.031(2) 0.0159(17) 0.0059(15) 0.0061(16) C13 0.0090(15) 0.0200(17) 0.0175(17) 0.0056(14) 0.0037(13) 0.0062(14) C14 0.0150(16) 0.0138(16) 0.0182(17) 0.0054(14) 0.0064(13) 0.0054(14) C15 0.029(2) 0.0216(18) 0.0181(18) 0.0087(15) 0.0114(15) 0.0104(17) C16 0.031(2) 0.0239(19) 0.0143(17) 0.0077(15) 0.0077(15) 0.0124(17) C17 0.0239(18) 0.0158(16) 0.0118(16) 0.0001(13) 0.0025(14) 0.0072(15) C18 0.0182(17) 0.0117(15) 0.0135(16) -0.0010(13) 0.0008(13) 0.0047(14) C19 0.0203(18) 0.0148(16) 0.0193(18) 0.0052(14) 0.0054(14) 0.0092(15) C20 0.0165(17) 0.0196(17) 0.027(2) 0.0092(15) 0.0043(15) 0.0106(15) C21 0.0214(18) 0.0151(17) 0.0219(19) -0.0004(14) 0.0006(15) 0.0100(15) C22 0.0212(18) 0.0249(19) 0.0154(17) 0.0030(15) 0.0050(14) 0.0168(16) C23 0.0163(18) 0.028(2) 0.028(2) 0.0102(17) 0.0075(15) 0.0123(16) C24 0.0184(18) 0.0238(19) 0.028(2) 0.0059(16) 0.0001(15) 0.0075(16) C25 0.0211(18) 0.0204(18) 0.0142(17) 0.0006(14) -0.0029(14) 0.0103(15) C26 0.030(2) 0.0272(19) 0.0139(17) 0.0088(15) 0.0056(15) 0.0162(17) C27 0.045(3) 0.036(2) 0.033(2) 0.024(2) 0.017(2) 0.027(2) C28 0.031(2) 0.0188(18) 0.037(2) 0.0137(17) 0.0073(18) 0.0135(17) C29 0.027(2) 0.046(3) 0.061(3) 0.035(3) 0.008(2) 0.016(2) Cl2 0.0538(8) 0.0570(8) 0.0545(8) 0.0394(7) 0.0180(6) 0.0300(7) Cl3 0.0406(6) 0.0510(7) 0.0511(7) 0.0322(6) 0.0116(5) 0.0247(6) C30 0.075(5) 0.216(10) 0.074(5) 0.095(6) 0.038(4) 0.088(6) Cl4 0.0620(11) 0.1148(16) 0.1409(19) 0.0848(15) 0.0314(11) 0.0534(11) Cl5 0.127(2) 0.149(2) 0.139(2) 0.1019(19) 0.0163(17) 0.0759(18) _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 B1 2.166(4) . ? Ir1 C14 2.172(3) . ? Ir1 C13 2.175(3) . ? Ir1 C17 2.313(3) . ? Ir1 C18 2.314(3) . ? Ir1 S1 2.3801(10) . ? Ir1 S2 2.4827(9) . ? Ir1 H1 1.37(4) . ? Ir2 C26 2.103(4) . ? Ir2 C22 2.105(4) . ? Ir2 C25 2.115(3) . ? Ir2 C21 2.144(4) . ? Ir2 S3 2.3627(9) . ? Ir2 Cl1 2.3986(9) . ? N1 C1 1.344(4) . ? N1 C2 1.390(4) . ? N1 B1 1.571(5) . ? N2 C1 1.358(5) . ? N2 C3 1.388(5) . ? N2 C4 1.460(5) . ? N3 C5 1.342(4) . ? N3 C6 1.401(4) . ? N3 B1 1.580(5) . ? N4 C5 1.356(4) . ? N4 C7 1.395(5) . ? N4 C8 1.459(5) . ? N5 C9 1.355(4) . ? N5 C10 1.393(4) . ? N5 B1 1.577(4) . ? N6 C9 1.359(4) . ? N6 C11 1.384(5) . ? N6 C12 1.465(4) . ? S1 C1 1.721(4) . ? S2 C5 1.711(4) . ? S3 C9 1.741(4) . ? C2 C3 1.357(5) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 C7 1.343(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.348(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.408(5) . ? C13 C20 1.534(5) . ? C13 H13 1.0000 . ? C14 C15 1.520(5) . ? C14 H14 1.0000 . ? C15 C16 1.536(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.523(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.384(5) . ? C17 H17 1.0000 . ? C18 C19 1.521(5) . ? C18 H18 1.0000 . ? C19 C20 1.546(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.418(5) . ? C21 C28 1.525(6) . ? C21 H21 1.0000 . ? C22 C23 1.521(5) . ? C22 H22 1.0000 . ? C23 C24 1.526(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.532(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.410(5) . ? C25 H25 1.0000 . ? C26 C27 1.522(5) . ? C26 H26 1.0000 . ? C27 C28 1.535(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 Cl2 1.772(5) . ? C29 Cl3 1.774(5) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 Cl5 1.646(7) . ? C30 Cl4 1.699(7) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? 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 B1 Ir1 C14 94.13(14) . . ? B1 Ir1 C13 100.34(14) . . ? C14 Ir1 C13 37.81(13) . . ? B1 Ir1 C17 158.29(14) . . ? C14 Ir1 C17 79.33(13) . . ? C13 Ir1 C17 87.21(14) . . ? B1 Ir1 C18 166.32(13) . . ? C14 Ir1 C18 94.68(13) . . ? C13 Ir1 C18 80.50(13) . . ? C17 Ir1 C18 34.80(13) . . ? B1 Ir1 S1 85.27(10) . . ? C14 Ir1 S1 151.81(10) . . ? C13 Ir1 S1 169.16(10) . . ? C17 Ir1 S1 90.88(10) . . ? C18 Ir1 S1 91.86(9) . . ? B1 Ir1 S2 85.63(10) . . ? C14 Ir1 S2 118.41(10) . . ? C13 Ir1 S2 81.57(10) . . ? C17 Ir1 S2 115.76(10) . . ? C18 Ir1 S2 80.97(9) . . ? S1 Ir1 S2 89.69(3) . . ? B1 Ir1 H1 81.3(16) . . ? C14 Ir1 H1 71.2(16) . . ? C13 Ir1 H1 109.0(16) . . ? C17 Ir1 H1 76.9(16) . . ? C18 Ir1 H1 111.4(15) . . ? S1 Ir1 H1 80.9(16) . . ? S2 Ir1 H1 164.5(16) . . ? C26 Ir2 C22 97.78(15) . . ? C26 Ir2 C25 39.08(15) . . ? C22 Ir2 C25 81.19(15) . . ? C26 Ir2 C21 81.72(15) . . ? C22 Ir2 C21 38.97(15) . . ? C25 Ir2 C21 90.53(14) . . ? C26 Ir2 S3 88.83(11) . . ? C22 Ir2 S3 153.95(11) . . ? C25 Ir2 S3 88.55(11) . . ? C21 Ir2 S3 166.02(11) . . ? C26 Ir2 Cl1 155.23(11) . . ? C22 Ir2 Cl1 90.24(10) . . ? C25 Ir2 Cl1 165.29(11) . . ? C21 Ir2 Cl1 90.23(10) . . ? S3 Ir2 Cl1 94.19(3) . . ? C1 N1 C2 107.9(3) . . ? C1 N1 B1 119.9(3) . . ? C2 N1 B1 130.8(3) . . ? C1 N2 C3 108.6(3) . . ? C1 N2 C4 125.2(3) . . ? C3 N2 C4 126.2(3) . . ? C5 N3 C6 107.8(3) . . ? C5 N3 B1 122.0(3) . . ? C6 N3 B1 129.3(3) . . ? C5 N4 C7 108.4(3) . . ? C5 N4 C8 124.8(3) . . ? C7 N4 C8 126.8(3) . . ? C9 N5 C10 107.6(3) . . ? C9 N5 B1 128.8(3) . . ? C10 N5 B1 122.8(3) . . ? C9 N6 C11 108.8(3) . . ? C9 N6 C12 125.3(3) . . ? C11 N6 C12 125.8(3) . . ? C1 S1 Ir1 98.06(12) . . ? C5 S2 Ir1 96.64(12) . . ? C9 S3 Ir2 108.30(12) . . ? N1 B1 N5 108.8(3) . . ? N1 B1 N3 104.1(3) . . ? N5 B1 N3 105.0(3) . . ? N1 B1 Ir1 109.1(2) . . ? N5 B1 Ir1 118.7(2) . . ? N3 B1 Ir1 110.2(2) . . ? N1 C1 N2 108.5(3) . . ? N1 C1 S1 123.5(3) . . ? N2 C1 S1 127.9(3) . . ? C3 C2 N1 108.4(3) . . ? C3 C2 H2 125.8 . . ? N1 C2 H2 125.8 . . ? C2 C3 N2 106.6(3) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N4 108.5(3) . . ? N3 C5 S2 125.1(3) . . ? N4 C5 S2 126.3(3) . . ? C7 C6 N3 108.1(3) . . ? C7 C6 H6 125.9 . . ? N3 C6 H6 125.9 . . ? C6 C7 N4 107.1(3) . . ? C6 C7 H7 126.4 . . ? N4 C7 H7 126.4 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 N6 108.0(3) . . ? N5 C9 S3 127.7(3) . . ? N6 C9 S3 124.2(3) . . ? C11 C10 N5 108.5(3) . . ? C11 C10 H10 125.8 . . ? N5 C10 H10 125.7 . . ? C10 C11 N6 107.0(3) . . ? C10 C11 H11 126.5 . . ? N6 C11 H11 126.5 . . ? N6 C12 H12A 109.5 . . ? N6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C20 123.9(3) . . ? C14 C13 Ir1 71.0(2) . . ? C20 C13 Ir1 113.4(2) . . ? C14 C13 H13 113.8 . . ? C20 C13 H13 113.8 . . ? Ir1 C13 H13 113.8 . . ? C13 C14 C15 124.8(3) . . ? C13 C14 Ir1 71.21(19) . . ? C15 C14 Ir1 112.0(2) . . ? C13 C14 H14 113.8 . . ? C15 C14 H14 113.8 . . ? Ir1 C14 H14 113.8 . . ? C14 C15 C16 113.6(3) . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 113.5(3) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 122.2(4) . . ? C18 C17 Ir1 72.6(2) . . ? C16 C17 Ir1 110.8(2) . . ? C18 C17 H17 114.7 . . ? C16 C17 H17 114.7 . . ? Ir1 C17 H17 114.7 . . ? C17 C18 C19 123.7(3) . . ? C17 C18 Ir1 72.6(2) . . ? C19 C18 Ir1 108.1(2) . . ? C17 C18 H18 114.8 . . ? C19 C18 H18 114.8 . . ? Ir1 C18 H18 114.8 . . ? C18 C19 C20 114.1(3) . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C13 C20 C19 116.0(3) . . ? C13 C20 H20A 108.3 . . ? C19 C20 H20A 108.3 . . ? C13 C20 H20B 108.3 . . ? C19 C20 H20B 108.3 . . ? H20A C20 H20B 107.4 . . ? C22 C21 C28 121.7(3) . . ? C22 C21 Ir2 69.0(2) . . ? C28 C21 Ir2 113.4(3) . . ? C22 C21 H21 114.9 . . ? C28 C21 H21 114.9 . . ? Ir2 C21 H21 114.9 . . ? C21 C22 C23 123.4(3) . . ? C21 C22 Ir2 72.0(2) . . ? C23 C22 Ir2 113.2(2) . . ? C21 C22 H22 113.8 . . ? C23 C22 H22 113.8 . . ? Ir2 C22 H22 113.8 . . ? C22 C23 C24 112.6(3) . . ? C22 C23 H23A 109.1 . . ? C24 C23 H23A 109.1 . . ? C22 C23 H23B 109.1 . . ? C24 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? C23 C24 C25 111.7(3) . . ? C23 C24 H24A 109.3 . . ? C25 C24 H24A 109.3 . . ? C23 C24 H24B 109.3 . . ? C25 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? C26 C25 C24 122.8(3) . . ? C26 C25 Ir2 70.0(2) . . ? C24 C25 Ir2 114.9(2) . . ? C26 C25 H25 113.9 . . ? C24 C25 H25 113.9 . . ? Ir2 C25 H25 113.9 . . ? C25 C26 C27 124.8(4) . . ? C25 C26 Ir2 70.9(2) . . ? C27 C26 Ir2 111.7(3) . . ? C25 C26 H26 113.9 . . ? C27 C26 H26 113.9 . . ? Ir2 C26 H26 113.9 . . ? C26 C27 C28 112.5(3) . . ? C26 C27 H27A 109.1 . . ? C28 C27 H27A 109.1 . . ? C26 C27 H27B 109.1 . . ? C28 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C21 C28 C27 111.6(3) . . ? C21 C28 H28A 109.3 . . ? C27 C28 H28A 109.3 . . ? C21 C28 H28B 109.3 . . ? C27 C28 H28B 109.3 . . ? H28A C28 H28B 108.0 . . ? Cl2 C29 Cl3 111.2(3) . . ? Cl2 C29 H29A 109.4 . . ? Cl3 C29 H29A 109.4 . . ? Cl2 C29 H29B 109.4 . . ? Cl3 C29 H29B 109.4 . . ? H29A C29 H29B 108.0 . . ? Cl5 C30 Cl4 120.7(4) . . ? Cl5 C30 H30A 107.1 . . ? Cl4 C30 H30A 107.1 . . ? Cl5 C30 H30B 107.1 . . ? Cl4 C30 H30B 107.1 . . ? H30A C30 H30B 106.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag B1 Ir1 S1 C1 13.47(15) . . . . ? C14 Ir1 S1 C1 -76.4(2) . . . . ? C13 Ir1 S1 C1 135.2(5) . . . . ? C17 Ir1 S1 C1 -145.14(15) . . . . ? C18 Ir1 S1 C1 -179.93(15) . . . . ? S2 Ir1 S1 C1 99.11(12) . . . . ? B1 Ir1 S2 C5 -2.32(16) . . . . ? C14 Ir1 S2 C5 90.01(16) . . . . ? C13 Ir1 S2 C5 98.82(15) . . . . ? C17 Ir1 S2 C5 -178.43(16) . . . . ? C18 Ir1 S2 C5 -179.54(15) . . . . ? S1 Ir1 S2 C5 -87.61(12) . . . . ? C26 Ir2 S3 C9 158.38(16) . . . . ? C22 Ir2 S3 C9 -96.2(3) . . . . ? C25 Ir2 S3 C9 -162.54(16) . . . . ? C21 Ir2 S3 C9 111.1(4) . . . . ? Cl1 Ir2 S3 C9 2.99(12) . . . . ? C1 N1 B1 N5 151.4(3) . . . . ? C2 N1 B1 N5 -44.2(4) . . . . ? C1 N1 B1 N3 -97.0(3) . . . . ? C2 N1 B1 N3 67.4(4) . . . . ? C1 N1 B1 Ir1 20.5(4) . . . . ? C2 N1 B1 Ir1 -175.1(3) . . . . ? C9 N5 B1 N1 -49.0(4) . . . . ? C10 N5 B1 N1 142.8(3) . . . . ? C9 N5 B1 N3 -159.9(3) . . . . ? C10 N5 B1 N3 31.8(4) . . . . ? C9 N5 B1 Ir1 76.5(4) . . . . ? C10 N5 B1 Ir1 -91.8(3) . . . . ? C5 N3 B1 N1 108.8(3) . . . . ? C6 N3 B1 N1 -59.4(4) . . . . ? C5 N3 B1 N5 -136.9(3) . . . . ? C6 N3 B1 N5 54.9(4) . . . . ? C5 N3 B1 Ir1 -8.0(4) . . . . ? C6 N3 B1 Ir1 -176.2(3) . . . . ? C14 Ir1 B1 N1 133.2(2) . . . . ? C13 Ir1 B1 N1 170.9(2) . . . . ? C17 Ir1 B1 N1 61.9(5) . . . . ? C18 Ir1 B1 N1 -96.8(6) . . . . ? S1 Ir1 B1 N1 -18.5(2) . . . . ? S2 Ir1 B1 N1 -108.5(2) . . . . ? C14 Ir1 B1 N5 7.9(3) . . . . ? C13 Ir1 B1 N5 45.5(3) . . . . ? C17 Ir1 B1 N5 -63.4(5) . . . . ? C18 Ir1 B1 N5 137.8(5) . . . . ? S1 Ir1 B1 N5 -143.8(3) . . . . ? S2 Ir1 B1 N5 126.1(2) . . . . ? C14 Ir1 B1 N3 -113.1(2) . . . . ? C13 Ir1 B1 N3 -75.5(2) . . . . ? C17 Ir1 B1 N3 175.6(3) . . . . ? C18 Ir1 B1 N3 16.8(7) . . . . ? S1 Ir1 B1 N3 95.2(2) . . . . ? S2 Ir1 B1 N3 5.1(2) . . . . ? C2 N1 C1 N2 0.2(4) . . . . ? B1 N1 C1 N2 167.8(3) . . . . ? C2 N1 C1 S1 -175.9(2) . . . . ? B1 N1 C1 S1 -8.3(4) . . . . ? C3 N2 C1 N1 -0.5(4) . . . . ? C4 N2 C1 N1 179.9(3) . . . . ? C3 N2 C1 S1 175.3(3) . . . . ? C4 N2 C1 S1 -4.2(5) . . . . ? Ir1 S1 C1 N1 -7.0(3) . . . . ? Ir1 S1 C1 N2 177.7(3) . . . . ? C1 N1 C2 C3 0.3(4) . . . . ? B1 N1 C2 C3 -165.5(3) . . . . ? N1 C2 C3 N2 -0.6(4) . . . . ? C1 N2 C3 C2 0.7(4) . . . . ? C4 N2 C3 C2 -179.7(3) . . . . ? C6 N3 C5 N4 -0.9(4) . . . . ? B1 N3 C5 N4 -171.4(3) . . . . ? C6 N3 C5 S2 176.9(3) . . . . ? B1 N3 C5 S2 6.4(5) . . . . ? C7 N4 C5 N3 0.3(4) . . . . ? C8 N4 C5 N3 -176.7(3) . . . . ? C7 N4 C5 S2 -177.5(3) . . . . ? C8 N4 C5 S2 5.5(5) . . . . ? Ir1 S2 C5 N3 -1.4(3) . . . . ? Ir1 S2 C5 N4 176.0(3) . . . . ? C5 N3 C6 C7 1.3(4) . . . . ? B1 N3 C6 C7 170.8(3) . . . . ? N3 C6 C7 N4 -1.1(4) . . . . ? C5 N4 C7 C6 0.5(4) . . . . ? C8 N4 C7 C6 177.4(3) . . . . ? C10 N5 C9 N6 -0.7(4) . . . . ? B1 N5 C9 N6 -170.4(3) . . . . ? C10 N5 C9 S3 175.3(3) . . . . ? B1 N5 C9 S3 5.6(5) . . . . ? C11 N6 C9 N5 0.0(4) . . . . ? C12 N6 C9 N5 -176.8(3) . . . . ? C11 N6 C9 S3 -176.2(3) . . . . ? C12 N6 C9 S3 7.1(5) . . . . ? Ir2 S3 C9 N5 104.2(3) . . . . ? Ir2 S3 C9 N6 -80.4(3) . . . . ? C9 N5 C10 C11 1.2(4) . . . . ? B1 N5 C10 C11 171.6(3) . . . . ? N5 C10 C11 N6 -1.2(4) . . . . ? C9 N6 C11 C10 0.8(4) . . . . ? C12 N6 C11 C10 177.5(3) . . . . ? B1 Ir1 C13 C14 -83.4(2) . . . . ? C17 Ir1 C13 C14 76.1(2) . . . . ? C18 Ir1 C13 C14 110.5(2) . . . . ? S1 Ir1 C13 C14 156.2(4) . . . . ? S2 Ir1 C13 C14 -167.3(2) . . . . ? B1 Ir1 C13 C20 157.1(3) . . . . ? C14 Ir1 C13 C20 -119.5(3) . . . . ? C17 Ir1 C13 C20 -43.4(3) . . . . ? C18 Ir1 C13 C20 -9.0(2) . . . . ? S1 Ir1 C13 C20 36.6(7) . . . . ? S2 Ir1 C13 C20 73.1(2) . . . . ? C20 C13 C14 C15 1.8(5) . . . . ? Ir1 C13 C14 C15 -104.2(3) . . . . ? C20 C13 C14 Ir1 106.0(3) . . . . ? B1 Ir1 C14 C13 101.6(2) . . . . ? C17 Ir1 C14 C13 -99.3(2) . . . . ? C18 Ir1 C14 C13 -67.9(2) . . . . ? S1 Ir1 C14 C13 -170.74(17) . . . . ? S2 Ir1 C14 C13 14.3(2) . . . . ? B1 Ir1 C14 C15 -137.6(3) . . . . ? C13 Ir1 C14 C15 120.9(3) . . . . ? C17 Ir1 C14 C15 21.5(3) . . . . ? C18 Ir1 C14 C15 52.9(3) . . . . ? S1 Ir1 C14 C15 -49.9(4) . . . . ? S2 Ir1 C14 C15 135.2(2) . . . . ? C13 C14 C15 C16 45.1(5) . . . . ? Ir1 C14 C15 C16 -36.7(4) . . . . ? C14 C15 C16 C17 33.5(5) . . . . ? C15 C16 C17 C18 -96.3(4) . . . . ? C15 C16 C17 Ir1 -14.3(4) . . . . ? B1 Ir1 C17 C18 -171.4(3) . . . . ? C14 Ir1 C17 C18 114.6(2) . . . . ? C13 Ir1 C17 C18 77.3(2) . . . . ? S1 Ir1 C17 C18 -92.0(2) . . . . ? S2 Ir1 C17 C18 -1.9(2) . . . . ? B1 Ir1 C17 C16 70.1(5) . . . . ? C14 Ir1 C17 C16 -4.0(3) . . . . ? C13 Ir1 C17 C16 -41.2(3) . . . . ? C18 Ir1 C17 C16 -118.6(4) . . . . ? S1 Ir1 C17 C16 149.4(3) . . . . ? S2 Ir1 C17 C16 -120.5(2) . . . . ? C16 C17 C18 C19 3.6(5) . . . . ? Ir1 C17 C18 C19 -100.4(3) . . . . ? C16 C17 C18 Ir1 104.1(3) . . . . ? B1 Ir1 C18 C17 166.4(5) . . . . ? C14 Ir1 C18 C17 -63.7(2) . . . . ? C13 Ir1 C18 C17 -98.9(2) . . . . ? S1 Ir1 C18 C17 88.9(2) . . . . ? S2 Ir1 C18 C17 178.2(2) . . . . ? B1 Ir1 C18 C19 -73.0(6) . . . . ? C14 Ir1 C18 C19 56.9(2) . . . . ? C13 Ir1 C18 C19 21.7(2) . . . . ? C17 Ir1 C18 C19 120.6(3) . . . . ? S1 Ir1 C18 C19 -150.6(2) . . . . ? S2 Ir1 C18 C19 -61.2(2) . . . . ? C17 C18 C19 C20 49.8(5) . . . . ? Ir1 C18 C19 C20 -30.9(4) . . . . ? C14 C13 C20 C19 -87.6(4) . . . . ? Ir1 C13 C20 C19 -5.4(4) . . . . ? C18 C19 C20 C13 25.4(5) . . . . ? C26 Ir2 C21 C22 113.4(2) . . . . ? C25 Ir2 C21 C22 75.2(2) . . . . ? S3 Ir2 C21 C22 161.3(3) . . . . ? Cl1 Ir2 C21 C22 -90.1(2) . . . . ? C26 Ir2 C21 C28 -3.1(3) . . . . ? C22 Ir2 C21 C28 -116.5(4) . . . . ? C25 Ir2 C21 C28 -41.3(3) . . . . ? S3 Ir2 C21 C28 44.8(6) . . . . ? Cl1 Ir2 C21 C28 153.4(3) . . . . ? C28 C21 C22 C23 -1.1(6) . . . . ? Ir2 C21 C22 C23 -106.3(3) . . . . ? C28 C21 C22 Ir2 105.2(3) . . . . ? C26 Ir2 C22 C21 -66.4(2) . . . . ? C25 Ir2 C22 C21 -101.9(2) . . . . ? S3 Ir2 C22 C21 -169.86(19) . . . . ? Cl1 Ir2 C22 C21 90.1(2) . . . . ? C26 Ir2 C22 C23 53.0(3) . . . . ? C25 Ir2 C22 C23 17.5(3) . . . . ? C21 Ir2 C22 C23 119.4(4) . . . . ? S3 Ir2 C22 C23 -50.5(4) . . . . ? Cl1 Ir2 C22 C23 -150.5(3) . . . . ? C21 C22 C23 C24 54.8(5) . . . . ? Ir2 C22 C23 C24 -28.3(4) . . . . ? C22 C23 C24 C25 24.7(5) . . . . ? C23 C24 C25 C26 -91.8(4) . . . . ? C23 C24 C25 Ir2 -10.4(4) . . . . ? C22 Ir2 C25 C26 114.1(2) . . . . ? C21 Ir2 C25 C26 76.1(2) . . . . ? S3 Ir2 C25 C26 -89.9(2) . . . . ? Cl1 Ir2 C25 C26 169.1(3) . . . . ? C26 Ir2 C25 C24 -117.8(4) . . . . ? C22 Ir2 C25 C24 -3.8(3) . . . . ? C21 Ir2 C25 C24 -41.7(3) . . . . ? S3 Ir2 C25 C24 152.2(3) . . . . ? Cl1 Ir2 C25 C24 51.2(6) . . . . ? C24 C25 C26 C27 3.7(6) . . . . ? Ir2 C25 C26 C27 -103.7(4) . . . . ? C24 C25 C26 Ir2 107.3(3) . . . . ? C22 Ir2 C26 C25 -65.6(2) . . . . ? C21 Ir2 C26 C25 -101.2(2) . . . . ? S3 Ir2 C26 C25 89.1(2) . . . . ? Cl1 Ir2 C26 C25 -173.4(2) . . . . ? C22 Ir2 C26 C27 55.2(3) . . . . ? C25 Ir2 C26 C27 120.8(4) . . . . ? C21 Ir2 C26 C27 19.6(3) . . . . ? S3 Ir2 C26 C27 -150.0(3) . . . . ? Cl1 Ir2 C26 C27 -52.6(5) . . . . ? C25 C26 C27 C28 48.2(6) . . . . ? Ir2 C26 C27 C28 -33.1(5) . . . . ? C22 C21 C28 C27 -92.8(5) . . . . ? Ir2 C21 C28 C27 -13.8(4) . . . . ? C26 C27 C28 C21 30.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 29.70 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 2.660 _refine_diff_density_min -2.237 _refine_diff_density_rms 0.150