# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Gebhard Haberhauer' _publ_contact_author_address ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 Heidelberg D-69120 GERMANY ; _publ_contact_author_email GEBHARD.HABERHAUER@URZ.UNI-HEIDELBERG.DE _publ_contact_author_phone '049 6221 54- 8429' _publ_contact_author_fax '049 6221 54- 4205' _publ_section_title ; A widely applicable concept for predictable induction of preferred configuration in C3-symmetric systems ; loop_ _publ_author_name 'Gebhard Haberhauer' 'Thomas Oeser' 'Frank Rominger' #========================================================================== data_gh35 _database_code_depnum_ccdc_archive 'CCDC 257958' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'in paper 3a' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C63 H69 F12 N15 O3 P2 Ru' _chemical_formula_weight 1475.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting cubic _symmetry_space_group_name_H-M P2(1)3 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' 'z, x, y' 'z+1/2, -x+1/2, -y' '-z+1/2, -x, y+1/2' '-z, x+1/2, -y+1/2' 'y, z, x' '-y, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x' '-y+1/2, -z, x+1/2' _cell_length_a 18.999(1) _cell_length_b 18.999(1) _cell_length_c 18.999(1) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 6858.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3983 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 18.57 _exptl_crystal_description irregular _exptl_crystal_colour orange _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3032 _exptl_absorpt_coefficient_mu 0.364 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9407 _exptl_absorpt_correction_T_max 0.9680 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36787 _diffrn_reflns_av_R_equivalents 0.0975 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 20.79 _reflns_number_total 2388 _reflns_number_gt 2311 _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. The two PF6-anion were found to be situated on threefold crystallographic axes. In the case of the phosphorous atom P1 the crystallographic axis does not coincide with the C3-axis of the PF6-moiety, which results in disorder of this anion. In order to refine this anion successfully, it has to be treated with appropriate SAME-constraints which consider its local molecular symmetry. ; _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^)+(0.0539P)^2^+6.5181P] 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 noref _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 0.04(5) _refine_ls_number_reflns 2388 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1030 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _refine_ls_shift/su_max 0.273 _refine_ls_shift/su_mean 0.018 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 Ru1 Ru 0.95490(3) 0.45490(3) 0.04510(3) 0.0261(3) Uani 1 3 d S . . P1 P 0.73106(10) 0.76894(10) 0.23106(10) 0.0395(9) Uani 1 3 d S . . P2 P 0.96777(9) 0.96777(9) 0.96777(9) 0.0399(8) Uani 1 3 d S . . F1 F 0.6981(18) 0.825(3) 0.273(2) 0.104(15) Uani 0.30 1 d P A 1 F2 F 0.7793(6) 0.8133(4) 0.2765(6) 0.063(3) Uani 0.60 1 d P A 1 F3 F 1.0005(9) 0.9427(17) 0.8935(16) 0.081(6) Uani 0.60 1 d P B 1 F1A F 0.6805(16) 0.8287(14) 0.2222(15) 0.15(2) Uani 0.40 1 d P A 2 F2A F 0.7888(8) 0.7706(11) 0.2948(8) 0.085(6) Uani 0.40 1 d P A 2 F3A F 0.9727(15) 0.931(2) 0.895(2) 0.088(12) Uani 0.40 1 d P B 2 F1B F 0.6753(13) 0.8133(18) 0.2880(11) 0.057(8) Uani 0.30 1 d P A 3 F4 F 0.99743(19) 1.0428(2) 0.9468(2) 0.0591(11) Uani 1 1 d . B . N3 N 0.7452(3) 0.1870(3) 0.1232(3) 0.0247(13) Uani 1 1 d . . . N6 N 0.8291(3) 0.1785(2) 0.0422(3) 0.0261(12) Uani 1 1 d . . . N9 N 0.6393(3) 0.2841(3) 0.1352(3) 0.0286(14) Uani 1 1 d . . . H9N H 0.658(3) 0.247(4) 0.161(3) 0.034 Uiso 1 1 d . . . N23 N 0.9772(2) 0.3482(3) 0.0521(3) 0.0262(13) Uani 1 1 d . . . N28 N 0.9575(3) 0.4405(2) -0.0625(3) 0.0313(13) Uani 1 1 d . . . O9 O 0.6649(2) 0.3321(2) 0.0289(2) 0.0305(11) Uani 1 1 d . . . C1 C 0.6025(3) 0.3458(3) 0.1607(3) 0.0278(16) Uani 1 1 d . . . H1 H 0.5821 0.3712 0.1194 0.033 Uiso 1 1 calc R . . C2 C 0.8037(3) 0.1555(3) 0.1058(3) 0.0245(16) Uani 1 1 d . . . C4 C 0.7316(3) 0.2323(3) 0.0678(3) 0.0224(15) Uani 1 1 d . . . C5 C 0.7818(3) 0.2280(3) 0.0165(3) 0.0302(16) Uani 1 1 d . . . C7 C 0.7884(3) 0.2588(4) -0.0549(3) 0.0349(17) Uani 1 1 d . . . H7A H 0.7874 0.2211 -0.0900 0.052 Uiso 1 1 calc R . . H7B H 0.8330 0.2845 -0.0585 0.052 Uiso 1 1 calc R . . H7C H 0.7492 0.2912 -0.0633 0.052 Uiso 1 1 calc R . . C9 C 0.6753(3) 0.2866(3) 0.0743(4) 0.0240(16) Uani 1 1 d . . . C10 C 0.5417(3) 0.3257(3) 0.2109(3) 0.0327(16) Uani 1 1 d . . . H10 H 0.5617 0.2968 0.2501 0.039 Uiso 1 1 calc R . . C11 C 0.5075(4) 0.3912(4) 0.2429(4) 0.0426(19) Uani 1 1 d . . . H11A H 0.4848 0.4187 0.2057 0.064 Uiso 1 1 calc R . . H11B H 0.5436 0.4199 0.2660 0.064 Uiso 1 1 calc R . . H11C H 0.4722 0.3769 0.2777 0.064 Uiso 1 1 calc R . . C12 C 0.4889(4) 0.2811(4) 0.1718(4) 0.0443(19) Uani 1 1 d . . . H12A H 0.4671 0.3091 0.1343 0.066 Uiso 1 1 calc R . . H12B H 0.4524 0.2650 0.2046 0.066 Uiso 1 1 calc R . . H12C H 0.5128 0.2403 0.1512 0.066 Uiso 1 1 calc R . . C20 C 0.9000(3) 0.1680(3) 0.0126(3) 0.0271(16) Uani 1 1 d . . . H20A H 0.8963 0.1640 -0.0392 0.033 Uiso 1 1 calc R . . H20B H 0.9193 0.1230 0.0306 0.033 Uiso 1 1 calc R . . C21 C 0.9509(4) 0.2265(3) 0.0303(3) 0.0308(16) Uani 1 1 d . . . C22 C 0.9319(3) 0.2956(3) 0.0409(3) 0.0266(15) Uani 1 1 d . . . H22 H 0.8831 0.3066 0.0402 0.032 Uiso 1 1 calc R . . C24 C 1.0467(4) 0.3330(3) 0.0573(3) 0.0296(16) Uani 1 1 d . . . C25 C 1.0704(3) 0.2643(3) 0.0489(3) 0.0331(16) Uani 1 1 d . . . H25 H 1.1190 0.2538 0.0537 0.040 Uiso 1 1 calc R . . C26 C 1.0232(3) 0.2116(3) 0.0336(3) 0.0320(17) Uani 1 1 d . . . H26 H 1.0395 0.1651 0.0252 0.038 Uiso 1 1 calc R . . C27 C 0.8933(4) 0.4327(3) -0.0932(3) 0.0307(18) Uani 1 1 d . . . C29 C 1.0155(4) 0.4338(3) -0.1043(4) 0.0387(19) Uani 1 1 d . . . H29 H 1.0604 0.4392 -0.0829 0.046 Uiso 1 1 calc R . . C30 C 1.0135(4) 0.4197(4) -0.1755(3) 0.0376(18) Uani 1 1 d . . . C31 C 0.9497(4) 0.4109(4) -0.2052(3) 0.0388(18) Uani 1 1 d . . . H31 H 0.9463 0.4000 -0.2539 0.047 Uiso 1 1 calc R . . C32 C 0.8882(4) 0.4176(4) -0.1649(4) 0.0389(18) Uani 1 1 d . . . H32 H 0.8434 0.4119 -0.1864 0.047 Uiso 1 1 calc R . . C33 C 1.0815(4) 0.4151(5) -0.2155(4) 0.056(2) Uani 1 1 d . . . H33A H 1.0831 0.3706 -0.2417 0.084 Uiso 1 1 calc R . . H33B H 1.1211 0.4170 -0.1825 0.084 Uiso 1 1 calc R . . H33C H 1.0848 0.4546 -0.2485 0.084 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 Ru1 0.0261(3) 0.0261(3) 0.0261(3) 0.0009(3) 0.0009(3) -0.0009(3) P1 0.0395(9) 0.0395(9) 0.0395(9) -0.0045(11) 0.0045(11) -0.0045(11) P2 0.0399(8) 0.0399(8) 0.0399(8) -0.0037(9) -0.0037(9) -0.0037(9) F1 0.09(3) 0.13(3) 0.09(3) 0.004(19) 0.12(2) 0.05(2) F2 0.052(6) 0.050(6) 0.085(9) -0.008(6) -0.038(6) -0.015(5) F3 0.086(12) 0.117(10) 0.042(10) -0.037(7) 0.001(11) -0.035(10) F1A 0.065(15) 0.099(17) 0.29(6) -0.07(2) -0.10(3) 0.047(12) F2A 0.035(9) 0.170(17) 0.050(9) 0.026(14) 0.000(6) -0.007(13) F3A 0.11(2) 0.10(2) 0.052(19) -0.044(17) -0.07(2) 0.03(2) F1B 0.019(13) 0.15(2) 0.000(9) 0.032(10) 0.045(10) 0.049(14) F4 0.050(2) 0.053(3) 0.074(3) 0.020(3) 0.023(2) 0.008(2) N3 0.017(3) 0.028(3) 0.029(3) -0.005(3) 0.005(3) 0.000(3) N6 0.029(3) 0.026(3) 0.023(3) -0.007(3) 0.007(3) 0.000(2) N9 0.023(3) 0.028(3) 0.035(4) 0.007(3) -0.003(3) 0.008(3) N23 0.022(3) 0.031(3) 0.026(3) 0.000(3) 0.008(2) 0.001(3) N28 0.037(3) 0.021(3) 0.035(3) -0.002(2) -0.004(3) 0.002(3) O9 0.033(3) 0.034(3) 0.025(3) 0.002(2) 0.003(2) 0.000(2) C1 0.027(4) 0.033(4) 0.023(4) 0.001(3) -0.001(3) 0.004(3) C2 0.034(4) 0.024(4) 0.016(4) -0.002(3) 0.002(3) 0.002(3) C4 0.023(4) 0.018(3) 0.026(4) 0.000(3) 0.004(3) -0.004(3) C5 0.032(4) 0.026(4) 0.032(4) -0.004(3) -0.005(4) -0.013(3) C7 0.036(4) 0.047(4) 0.022(4) 0.001(3) 0.006(3) -0.004(3) C9 0.021(4) 0.027(4) 0.025(4) -0.001(4) -0.006(3) -0.006(3) C10 0.027(4) 0.034(4) 0.038(4) 0.005(3) 0.007(4) 0.002(4) C11 0.033(4) 0.045(5) 0.050(5) -0.005(4) 0.011(4) 0.000(4) C12 0.029(4) 0.051(5) 0.053(5) 0.003(4) 0.003(4) -0.009(4) C20 0.029(4) 0.019(3) 0.033(4) -0.008(3) 0.007(3) -0.004(3) C21 0.035(4) 0.035(4) 0.022(4) 0.004(3) 0.007(3) 0.002(4) C22 0.020(3) 0.035(4) 0.024(4) 0.005(3) -0.003(3) 0.001(3) C24 0.034(4) 0.042(4) 0.014(3) -0.002(3) -0.002(3) -0.002(4) C25 0.030(4) 0.035(4) 0.034(4) 0.005(4) 0.001(3) 0.006(3) C26 0.032(4) 0.034(4) 0.030(4) -0.008(3) 0.012(3) 0.003(3) C27 0.044(5) 0.018(4) 0.030(4) 0.011(3) 0.002(4) 0.002(3) C29 0.037(4) 0.034(4) 0.045(5) 0.003(4) 0.003(4) 0.003(3) C30 0.036(5) 0.052(5) 0.024(4) 0.003(3) -0.003(4) 0.009(4) C31 0.047(5) 0.048(4) 0.021(4) -0.004(3) -0.001(4) 0.010(4) C32 0.049(5) 0.039(4) 0.029(4) -0.001(3) -0.008(4) 0.014(4) C33 0.048(5) 0.081(6) 0.038(5) 0.003(4) 0.016(4) 0.010(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru1 N28 2.064(5) 8_645 ? Ru1 N28 2.064(5) . ? Ru1 N28 2.064(5) 11_556 ? Ru1 N23 2.075(5) 8_645 ? Ru1 N23 2.075(5) . ? Ru1 N23 2.075(5) 11_556 ? P1 F1A 1.497(19) . ? P1 F1A 1.497(19) 12_664 ? P1 F1A 1.497(19) 6_566 ? P1 F2 1.516(9) 6_566 ? P1 F2 1.516(9) . ? P1 F2 1.516(9) 12_664 ? P1 F1B 1.73(3) 12_664 ? P1 F1B 1.73(3) . ? P1 F1B 1.73(3) 6_566 ? P1 F2A 1.635(15) 12_664 ? P1 F2A 1.635(15) 6_566 ? P1 F2A 1.635(15) . ? P2 F3A 1.55(4) 9 ? P2 F3A 1.55(4) . ? P2 F3A 1.55(4) 5 ? P2 F4 1.584(5) 9 ? P2 F4 1.584(5) 5 ? P2 F4 1.584(5) . ? P2 F3 1.61(3) 9 ? P2 F3 1.61(3) . ? P2 F3 1.61(3) 5 ? F1 F2 1.56(4) . ? F1A F1A 1.26(4) 12_664 ? F1A F1A 1.26(4) 6_566 ? F2A F2A 1.68(4) 12_664 ? F2A F2A 1.68(4) 6_566 ? N3 C2 1.305(8) . ? N3 C4 1.384(7) . ? N6 C2 1.373(8) . ? N6 C5 1.389(8) . ? N6 C20 1.474(8) . ? N9 C9 1.346(8) . ? N9 C1 1.449(8) . ? N9 H9N 0.93(7) . ? N23 C22 1.336(7) . ? N23 C24 1.355(8) . ? N28 C27 1.361(8) . ? N28 C29 1.364(9) . ? O9 C9 1.237(7) . ? C1 C2 1.522(9) 11_556 ? C1 C10 1.545(9) . ? C1 H1 1.0000 . ? C2 C1 1.522(9) 8_645 ? C4 C5 1.368(8) . ? C4 C9 1.491(9) . ? C5 C7 1.481(9) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C10 C12 1.508(10) . ? C10 C11 1.529(9) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C20 C21 1.511(8) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.376(8) . ? C21 C26 1.403(9) . ? C22 H22 0.9500 . ? C24 C25 1.391(9) . ? C24 C27 1.457(9) 8_645 ? C25 C26 1.375(9) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.397(9) . ? C27 C24 1.457(9) 11_556 ? C29 C30 1.378(9) . ? C29 H29 0.9500 . ? C30 C31 1.348(10) . ? C30 C33 1.503(10) . ? C31 C32 1.401(10) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 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 N28 Ru1 N28 96.37(19) 8_645 . ? N28 Ru1 N28 96.37(19) 8_645 11_556 ? N28 Ru1 N28 96.36(19) . 11_556 ? N28 Ru1 N23 85.93(19) 8_645 8_645 ? N28 Ru1 N23 175.2(2) . 8_645 ? N28 Ru1 N23 79.2(2) 11_556 8_645 ? N28 Ru1 N23 79.2(2) 8_645 . ? N28 Ru1 N23 85.93(19) . . ? N28 Ru1 N23 175.2(2) 11_556 . ? N23 Ru1 N23 98.61(16) 8_645 . ? N28 Ru1 N23 175.2(2) 8_645 11_556 ? N28 Ru1 N23 79.2(2) . 11_556 ? N28 Ru1 N23 85.93(19) 11_556 11_556 ? N23 Ru1 N23 98.61(17) 8_645 11_556 ? N23 Ru1 N23 98.61(17) . 11_556 ? F1A P1 F1A 49.9(17) . 12_664 ? F1A P1 F1A 49.9(17) . 6_566 ? F1A P1 F1A 49.9(17) 12_664 6_566 ? F1A P1 F2 139.7(12) . 6_566 ? F1A P1 F2 98.2(16) 12_664 6_566 ? F1A P1 F2 91.8(10) 6_566 6_566 ? F1A P1 F2 91.8(10) . . ? F1A P1 F2 139.7(12) 12_664 . ? F1A P1 F2 98.2(16) 6_566 . ? F2 P1 F2 108.0(4) 6_566 . ? F1A P1 F2 98.2(16) . 12_664 ? F1A P1 F2 91.8(10) 12_664 12_664 ? F1A P1 F2 139.7(13) 6_566 12_664 ? F2 P1 F2 108.0(4) 6_566 12_664 ? F2 P1 F2 108.0(4) . 12_664 ? F1A P1 F1B 95.3(12) . 12_664 ? F1A P1 F1B 46.3(15) 12_664 12_664 ? F1A P1 F1B 83.3(15) 6_566 12_664 ? F2 P1 F1B 63.8(11) 6_566 12_664 ? F2 P1 F1B 171.8(11) . 12_664 ? F2 P1 F1B 75.2(11) 12_664 12_664 ? F1A P1 F1B 46.3(15) . . ? F1A P1 F1B 83.3(15) 12_664 . ? F1A P1 F1B 95.3(12) 6_566 . ? F2 P1 F1B 171.8(11) 6_566 . ? F2 P1 F1B 75.2(11) . . ? F2 P1 F1B 63.8(11) 12_664 . ? F1B P1 F1B 112.8(6) 12_664 . ? F1A P1 F1B 83.3(15) . 6_566 ? F1A P1 F1B 95.3(12) 12_664 6_566 ? F1A P1 F1B 46.3(15) 6_566 6_566 ? F2 P1 F1B 75.2(11) 6_566 6_566 ? F2 P1 F1B 63.8(11) . 6_566 ? F2 P1 F1B 171.8(11) 12_664 6_566 ? F1B P1 F1B 112.8(6) 12_664 6_566 ? F1B P1 F1B 112.8(6) . 6_566 ? F1A P1 F2A 128.7(16) . 12_664 ? F1A P1 F2A 120.0(11) 12_664 12_664 ? F1A P1 F2A 169.3(17) 6_566 12_664 ? F2 P1 F2A 86.3(8) 6_566 12_664 ? F2 P1 F2A 92.4(9) . 12_664 ? F2 P1 F2A 32.9(6) 12_664 12_664 ? F1B P1 F2A 86.4(10) 12_664 12_664 ? F1B P1 F2A 85.9(10) . 12_664 ? F1B P1 F2A 142.3(11) 6_566 12_664 ? F1A P1 F2A 169.3(17) . 6_566 ? F1A P1 F2A 128.7(16) 12_664 6_566 ? F1A P1 F2A 120.0(11) 6_566 6_566 ? F2 P1 F2A 32.9(6) 6_566 6_566 ? F2 P1 F2A 86.3(9) . 6_566 ? F2 P1 F2A 92.4(9) 12_664 6_566 ? F1B P1 F2A 85.9(10) 12_664 6_566 ? F1B P1 F2A 142.3(10) . 6_566 ? F1B P1 F2A 86.4(10) 6_566 6_566 ? F2A P1 F2A 62.0(12) 12_664 6_566 ? F1A P1 F2A 120.0(11) . . ? F1A P1 F2A 169.3(17) 12_664 . ? F1A P1 F2A 128.7(17) 6_566 . ? F2 P1 F2A 92.4(9) 6_566 . ? F2 P1 F2A 32.9(6) . . ? F2 P1 F2A 86.3(8) 12_664 . ? F1B P1 F2A 142.3(10) 12_664 . ? F1B P1 F2A 86.4(10) . . ? F1B P1 F2A 85.9(10) 6_566 . ? F2A P1 F2A 62.0(12) 12_664 . ? F2A P1 F2A 62.0(12) 6_566 . ? F3A P2 F3A 71.4(17) 9 . ? F3A P2 F3A 71.4(17) 9 5 ? F3A P2 F3A 71.4(17) . 5 ? F3A P2 F4 99.1(14) 9 9 ? F3A P2 F4 98.7(12) . 9 ? F3A P2 F4 167.8(11) 5 9 ? F3A P2 F4 98.7(12) 9 5 ? F3A P2 F4 167.8(11) . 5 ? F3A P2 F4 99.1(14) 5 5 ? F4 P2 F4 89.8(3) 9 5 ? F3A P2 F4 167.8(11) 9 . ? F3A P2 F4 99.1(14) . . ? F3A P2 F4 98.7(12) 5 . ? F4 P2 F4 89.8(3) 9 . ? F4 P2 F4 89.8(3) 5 . ? F3A P2 F3 20.7(13) 9 9 ? F3A P2 F3 88(2) . 9 ? F3A P2 F3 88(2) 5 9 ? F4 P2 F3 84.7(11) 9 9 ? F4 P2 F3 83.7(9) 5 9 ? F4 P2 F3 171.5(7) . 9 ? F3A P2 F3 88(2) 9 . ? F3A P2 F3 20.7(13) . . ? F3A P2 F3 88(2) 5 . ? F4 P2 F3 83.7(9) 9 . ? F4 P2 F3 171.5(7) 5 . ? F4 P2 F3 84.7(11) . . ? F3 P2 F3 101.1(7) 9 . ? F3A P2 F3 88(2) 9 5 ? F3A P2 F3 88(2) . 5 ? F3A P2 F3 20.7(13) 5 5 ? F4 P2 F3 171.5(7) 9 5 ? F4 P2 F3 84.7(11) 5 5 ? F4 P2 F3 83.7(9) . 5 ? F3 P2 F3 101.1(7) 9 5 ? F3 P2 F3 101.1(7) . 5 ? P1 F1 F2 60.1(13) . . ? P1 F2 F1 56.7(19) . . ? F1A F1A F1A 60.000(5) 12_664 6_566 ? F1A F1A P1 65.1(8) 12_664 . ? F1A F1A P1 65.1(8) 6_566 . ? P1 F2A F2A 59.0(6) . 12_664 ? P1 F2A F2A 59.0(6) . 6_566 ? F2A F2A F2A 60.000(3) 12_664 6_566 ? C2 N3 C4 104.6(5) . . ? C2 N6 C5 107.3(5) . . ? C2 N6 C20 127.9(5) . . ? C5 N6 C20 123.3(5) . . ? C9 N9 C1 120.3(5) . . ? C9 N9 H9N 106(4) . . ? C1 N9 H9N 129(4) . . ? C22 N23 C24 118.7(5) . . ? C22 N23 Ru1 126.1(4) . . ? C24 N23 Ru1 114.3(4) . . ? C27 N28 C29 117.8(5) . . ? C27 N28 Ru1 114.6(4) . . ? C29 N28 Ru1 127.5(4) . . ? N9 C1 C2 108.5(5) . 11_556 ? N9 C1 C10 111.5(5) . . ? C2 C1 C10 111.8(5) 11_556 . ? N9 C1 H1 108.3 . . ? C2 C1 H1 108.3 11_556 . ? C10 C1 H1 108.3 . . ? N3 C2 N6 112.1(5) . . ? N3 C2 C1 121.9(5) . 8_645 ? N6 C2 C1 125.9(6) . 8_645 ? C5 C4 N3 112.0(5) . . ? C5 C4 C9 126.9(6) . . ? N3 C4 C9 120.1(5) . . ? C4 C5 N6 103.9(5) . . ? C4 C5 C7 133.4(6) . . ? N6 C5 C7 122.3(6) . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O9 C9 N9 122.9(6) . . ? O9 C9 C4 122.8(6) . . ? N9 C9 C4 114.2(6) . . ? C12 C10 C11 111.8(6) . . ? C12 C10 C1 109.5(5) . . ? C11 C10 C1 111.2(5) . . ? C12 C10 H10 108.1 . . ? C11 C10 H10 108.1 . . ? C1 C10 H10 108.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N6 C20 C21 113.6(5) . . ? N6 C20 H20A 108.9 . . ? C21 C20 H20A 108.8 . . ? N6 C20 H20B 108.8 . . ? C21 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C26 116.3(6) . . ? C22 C21 C20 124.5(6) . . ? C26 C21 C20 119.2(6) . . ? N23 C22 C21 124.6(5) . . ? N23 C22 H22 117.7 . . ? C21 C22 H22 117.7 . . ? N23 C24 C25 120.4(6) . . ? N23 C24 C27 115.7(5) . 8_645 ? C25 C24 C27 123.8(6) . 8_645 ? C26 C25 C24 119.8(6) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C21 120.1(6) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? N28 C27 C32 120.1(6) . . ? N28 C27 C24 115.5(6) . 11_556 ? C32 C27 C24 124.4(6) . 11_556 ? N28 C29 C30 124.5(6) . . ? N28 C29 H29 117.8 . . ? C30 C29 H29 117.8 . . ? C31 C30 C29 117.4(7) . . ? C31 C30 C33 123.6(6) . . ? C29 C30 C33 118.9(7) . . ? C30 C31 C32 120.6(6) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C27 C32 C31 119.6(7) . . ? C27 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 F1A P1 F1 F2 -131(4) . . . . ? F1A P1 F1 F2 -152.3(11) 12_664 . . . ? F1A P1 F1 F2 -102.4(17) 6_566 . . . ? F2 P1 F1 F2 -35(9) 6_566 . . . ? F2 P1 F1 F2 115.3(11) 12_664 . . . ? F1B P1 F1 F2 -179.8(11) 12_664 . . . ? F1B P1 F1 F2 129(7) . . . . ? F1B P1 F1 F2 -57.3(10) 6_566 . . . ? F2A P1 F1 F2 87.8(13) 12_664 . . . ? F2A P1 F1 F2 34(3) 6_566 . . . ? F2A P1 F1 F2 27.9(9) . . . . ? F1A P1 F2 F1 29(2) . . . . ? F1A P1 F2 F1 46(3) 12_664 . . . ? F1A P1 F2 F1 79(2) 6_566 . . . ? F2 P1 F2 F1 173.6(17) 6_566 . . . ? F2 P1 F2 F1 -69.9(18) 12_664 . . . ? F1B P1 F2 F1 179(100) 12_664 . . . ? F1B P1 F2 F1 -14(2) . . . . ? F1B P1 F2 F1 111.0(16) 6_566 . . . ? F2A P1 F2 F1 -99.5(18) 12_664 . . . ? F2A P1 F2 F1 -161.2(17) 6_566 . . . ? F2A P1 F2 F1 -121(2) . . . . ? F1A P1 F1A F1A 66.9(5) 6_566 . . 12_664 ? F2 P1 F1A F1A 45(4) 6_566 . . 12_664 ? F2 P1 F1A F1A 166(2) . . . 12_664 ? F2 P1 F1A F1A -85(2) 12_664 . . 12_664 ? F1B P1 F1A F1A -10(2) 12_664 . . 12_664 ? F1B P1 F1A F1A -126(3) . . . 12_664 ? F1B P1 F1A F1A 103(2) 6_566 . . 12_664 ? F2A P1 F1A F1A -99(2) 12_664 . . 12_664 ? F2A P1 F1A F1A 87(7) 6_566 . . 12_664 ? F2A P1 F1A F1A -175.8(17) . . . 12_664 ? F1A P1 F1A F1A -66.9(5) 12_664 . . 6_566 ? F2 P1 F1A F1A -22(4) 6_566 . . 6_566 ? F2 P1 F1A F1A 99(3) . . . 6_566 ? F2 P1 F1A F1A -152(3) 12_664 . . 6_566 ? F1B P1 F1A F1A -77(3) 12_664 . . 6_566 ? F1B P1 F1A F1A 167(4) . . . 6_566 ? F1B P1 F1A F1A 36(3) 6_566 . . 6_566 ? F2A P1 F1A F1A -166(2) 12_664 . . 6_566 ? F2A P1 F1A F1A 20(7) 6_566 . . 6_566 ? F2A P1 F1A F1A 117.2(19) . . . 6_566 ? F1A P1 F2A F2A 120.7(18) . . . 12_664 ? F1A P1 F2A F2A 103(5) 12_664 . . 12_664 ? F1A P1 F2A F2A -178.7(13) 6_566 . . 12_664 ? F2 P1 F2A F2A -84.6(11) 6_566 . . 12_664 ? F2 P1 F2A F2A 155(2) . . . 12_664 ? F2 P1 F2A F2A 23.3(9) 12_664 . . 12_664 ? F1B P1 F2A F2A -36(2) 12_664 . . 12_664 ? F1B P1 F2A F2A 87.3(12) . . . 12_664 ? F1B P1 F2A F2A -159.5(12) 6_566 . . 12_664 ? F2A P1 F2A F2A -71.4(5) 6_566 . . 12_664 ? F1A P1 F2A F2A -167.9(19) . . . 6_566 ? F1A P1 F2A F2A 175(5) 12_664 . . 6_566 ? F1A P1 F2A F2A -107.4(11) 6_566 . . 6_566 ? F2 P1 F2A F2A -13.2(11) 6_566 . . 6_566 ? F2 P1 F2A F2A -133(2) . . . 6_566 ? F2 P1 F2A F2A 94.7(10) 12_664 . . 6_566 ? F1B P1 F2A F2A 35(2) 12_664 . . 6_566 ? F1B P1 F2A F2A 158.6(12) . . . 6_566 ? F1B P1 F2A F2A -88.1(12) 6_566 . . 6_566 ? F2A P1 F2A F2A 71.4(5) 12_664 . . 6_566 ? N28 Ru1 N23 C22 -172.9(5) 8_645 . . . ? N28 Ru1 N23 C22 -75.6(5) . . . . ? N28 Ru1 N23 C22 165(2) 11_556 . . . ? N23 Ru1 N23 C22 102.9(4) 8_645 . . . ? N23 Ru1 N23 C22 2.8(5) 11_556 . . . ? N28 Ru1 N23 C24 -4.1(4) 8_645 . . . ? N28 Ru1 N23 C24 93.2(4) . . . . ? N28 Ru1 N23 C24 -26(3) 11_556 . . . ? N23 Ru1 N23 C24 -88.3(5) 8_645 . . . ? N23 Ru1 N23 C24 171.6(4) 11_556 . . . ? N28 Ru1 N28 C27 177.1(4) 8_645 . . . ? N28 Ru1 N28 C27 -85.7(5) 11_556 . . . ? N23 Ru1 N28 C27 -64(3) 8_645 . . . ? N23 Ru1 N28 C27 98.5(4) . . . . ? N23 Ru1 N28 C27 -1.1(4) 11_556 . . . ? N28 Ru1 N28 C29 1.4(5) 8_645 . . . ? N28 Ru1 N28 C29 98.6(4) 11_556 . . . ? N23 Ru1 N28 C29 120(2) 8_645 . . . ? N23 Ru1 N28 C29 -77.2(5) . . . . ? N23 Ru1 N28 C29 -176.8(5) 11_556 . . . ? C9 N9 C1 C2 -80.3(7) . . . 11_556 ? C9 N9 C1 C10 156.1(5) . . . . ? C4 N3 C2 N6 0.5(7) . . . . ? C4 N3 C2 C1 177.7(5) . . . 8_645 ? C5 N6 C2 N3 -1.1(7) . . . . ? C20 N6 C2 N3 165.2(5) . . . . ? C5 N6 C2 C1 -178.2(6) . . . 8_645 ? C20 N6 C2 C1 -11.9(9) . . . 8_645 ? C2 N3 C4 C5 0.4(7) . . . . ? C2 N3 C4 C9 -169.2(5) . . . . ? N3 C4 C5 N6 -1.0(6) . . . . ? C9 C4 C5 N6 167.7(6) . . . . ? N3 C4 C5 C7 172.9(7) . . . . ? C9 C4 C5 C7 -18.4(11) . . . . ? C2 N6 C5 C4 1.3(6) . . . . ? C20 N6 C5 C4 -165.8(5) . . . . ? C2 N6 C5 C7 -173.5(6) . . . . ? C20 N6 C5 C7 19.4(9) . . . . ? C1 N9 C9 O9 -19.5(9) . . . . ? C1 N9 C9 C4 157.4(5) . . . . ? C5 C4 C9 O9 5.9(10) . . . . ? N3 C4 C9 O9 173.9(5) . . . . ? C5 C4 C9 N9 -171.0(6) . . . . ? N3 C4 C9 N9 -3.1(8) . . . . ? N9 C1 C10 C12 -61.3(7) . . . . ? C2 C1 C10 C12 177.0(5) 11_556 . . . ? N9 C1 C10 C11 174.7(5) . . . . ? C2 C1 C10 C11 53.0(7) 11_556 . . . ? C2 N6 C20 C21 -91.4(7) . . . . ? C5 N6 C20 C21 72.9(7) . . . . ? N6 C20 C21 C22 -30.3(9) . . . . ? N6 C20 C21 C26 152.6(6) . . . . ? C24 N23 C22 C21 -3.7(9) . . . . ? Ru1 N23 C22 C21 164.6(5) . . . . ? C26 C21 C22 N23 1.7(9) . . . . ? C20 C21 C22 N23 -175.5(6) . . . . ? C22 N23 C24 C25 2.0(9) . . . . ? Ru1 N23 C24 C25 -167.6(5) . . . . ? C22 N23 C24 C27 178.1(5) . . . 8_645 ? Ru1 N23 C24 C27 8.4(6) . . . 8_645 ? N23 C24 C25 C26 1.5(9) . . . . ? C27 C24 C25 C26 -174.3(6) 8_645 . . . ? C24 C25 C26 C21 -3.5(9) . . . . ? C22 C21 C26 C25 2.0(9) . . . . ? C20 C21 C26 C25 179.4(6) . . . . ? C29 N28 C27 C32 0.7(8) . . . . ? Ru1 N28 C27 C32 -175.5(5) . . . . ? C29 N28 C27 C24 -178.0(5) . . . 11_556 ? Ru1 N28 C27 C24 5.8(6) . . . 11_556 ? C27 N28 C29 C30 0.0(9) . . . . ? Ru1 N28 C29 C30 175.6(5) . . . . ? N28 C29 C30 C31 -1.1(11) . . . . ? N28 C29 C30 C33 178.8(6) . . . . ? C29 C30 C31 C32 1.5(10) . . . . ? C33 C30 C31 C32 -178.5(7) . . . . ? N28 C27 C32 C31 -0.3(10) . . . . ? C24 C27 C32 C31 178.3(6) 11_556 . . . ? C30 C31 C32 C27 -0.8(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 20.79 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.673 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.054 #========================================================================== data_gh39 _database_code_depnum_ccdc_archive 'CCDC 257959' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'in paper 3c' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C63 H78.60 Ir N12 O10.80' _chemical_formula_weight 1368.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' _cell_length_a 16.2136(13) _cell_length_b 16.2136(13) _cell_length_c 22.0711(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5024.7(7) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4638 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 25.48 _exptl_crystal_description polyhedron _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 2.057 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7343 _exptl_absorpt_correction_T_max 0.9222 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17200 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 28.32 _reflns_number_total 5546 _reflns_number_gt 5518 _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. Some of the five crystal water positions were only partially occupied. The occupation factors were fixed to values that result in similar and reasonable thermal parameters. ; _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^)+(0.0713P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.020(11) _refine_ls_number_reflns 5546 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1114 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 Ir1 Ir 0.6667 0.3333 0.208568(2) 0.02063(9) Uani 1 3 d S . . O9 O 0.3617(4) 0.0814(4) 0.4149(3) 0.0533(14) Uani 1 1 d . . . N3 N 0.5930(5) 0.1446(5) 0.4760(3) 0.0457(14) Uani 1 1 d . . . N6 N 0.4500(4) 0.3819(5) 0.4008(3) 0.0419(13) Uani 1 1 d . . . N9 N 0.4559(5) 0.1976(6) 0.4802(3) 0.0520(16) Uani 1 1 d . . . H9 H 0.5014 0.2150 0.5073 0.062 Uiso 1 1 calc R . . N28 N 0.5913(8) 0.2052(8) 0.1600(4) 0.040(2) Uani 1 1 d . . . C1 C 0.4035(6) 0.2491(6) 0.4770(4) 0.0497(18) Uani 1 1 d . . . H1 H 0.3504 0.2147 0.4474 0.060 Uiso 1 1 calc R . . C2 C 0.4676(5) 0.3447(6) 0.4518(3) 0.0455(17) Uani 1 1 d . . . C4 C 0.5139(5) 0.1016(5) 0.4384(3) 0.0422(15) Uani 1 1 d . . . C5 C 0.5281(6) 0.0535(5) 0.3912(4) 0.0426(16) Uani 1 1 d . . . C7 C 0.4667(6) -0.0022(5) 0.3408(4) 0.0458(17) Uani 1 1 d . . . H7A H 0.5000 0.0238 0.3024 0.069 Uiso 1 1 calc R . . H7B H 0.4079 0.0009 0.3416 0.069 Uiso 1 1 calc R . . H7C H 0.4511 -0.0687 0.3448 0.069 Uiso 1 1 calc R . . C9 C 0.4370(6) 0.1250(5) 0.4433(4) 0.0438(17) Uani 1 1 d . . . C10 C 0.3587(7) 0.2513(7) 0.5373(4) 0.063(3) Uani 1 1 d . . . H10 H 0.4103 0.2943 0.5659 0.076 Uiso 1 1 calc R . . C11 C 0.3029(10) 0.1519(8) 0.5656(5) 0.096(5) Uani 1 1 d . . . H11A H 0.2611 0.1064 0.5349 0.144 Uiso 1 1 calc R . . H11B H 0.2643 0.1534 0.5993 0.144 Uiso 1 1 calc R . . H11C H 0.3474 0.1324 0.5806 0.144 Uiso 1 1 calc R . . C12 C 0.2934(8) 0.2942(9) 0.5241(6) 0.083(4) Uani 1 1 d . . . H12A H 0.3329 0.3621 0.5147 0.125 Uiso 1 1 calc R . . H12B H 0.2542 0.2863 0.5598 0.125 Uiso 1 1 calc R . . H12C H 0.2521 0.2611 0.4895 0.125 Uiso 1 1 calc R . . C20 C 0.3795(5) 0.3251(6) 0.3538(4) 0.0448(16) Uani 1 1 d . . . H20A H 0.3654 0.3677 0.3292 0.054 Uiso 1 1 calc R . . H20B H 0.3196 0.2776 0.3737 0.054 Uiso 1 1 calc R . . C21 C 0.4144(5) 0.2737(5) 0.3121(3) 0.0345(13) Uani 1 1 d . . . C22 C 0.5097(4) 0.3145(4) 0.2963(3) 0.0276(11) Uani 1 1 d . . . H22 H 0.5551 0.3711 0.3162 0.033 Uiso 1 1 calc R . . C23 C 0.5410(7) 0.2749(8) 0.2519(5) 0.028(2) Uani 1 1 d . . . C24 C 0.4693(5) 0.1853(5) 0.2279(3) 0.0337(13) Uani 1 1 d . . . C25 C 0.3749(5) 0.1419(5) 0.2472(4) 0.0406(15) Uani 1 1 d . . . H25 H 0.3294 0.0816 0.2313 0.049 Uiso 1 1 calc R . . C26 C 0.3477(5) 0.1860(6) 0.2888(4) 0.0391(17) Uani 1 1 d . . . H26 H 0.2832 0.1566 0.3017 0.047 Uiso 1 1 calc R . . C27 C 0.5006(5) 0.1457(5) 0.1790(3) 0.0397(15) Uani 1 1 d . . . C29 C 0.6255(6) 0.1789(7) 0.1122(4) 0.053(2) Uani 1 1 d . . . H29 H 0.6885 0.2207 0.0986 0.063 Uiso 1 1 calc R . . C30 C 0.5717(8) 0.0934(8) 0.0830(5) 0.071(3) Uani 1 1 d . . . H30 H 0.5971 0.0767 0.0494 0.085 Uiso 1 1 calc R . . C31 C 0.4806(8) 0.0324(11) 0.1029(7) 0.081(5) Uani 1 1 d . . . H31 H 0.4425 -0.0267 0.0829 0.097 Uiso 1 1 calc R . . C32 C 0.4443(6) 0.0572(7) 0.1523(5) 0.060(3) Uani 1 1 d . . . H32 H 0.3825 0.0145 0.1675 0.072 Uiso 1 1 calc R . . O51 O 0.1275(6) 0.1658(7) 0.3563(4) 0.051(2) Uani 1 1 d . . . O52 O 0.9572(9) 0.1315(9) 0.4143(7) 0.078(4) Uani 0.80 1 d P . . O53 O 0.0605(12) 0.0937(12) 0.4865(7) 0.050(4) Uani 0.35 1 d P . . O54 O 0.5713(11) 0.3119(13) 0.5766(7) 0.048(4) Uani 0.35 1 d P . . O55 O 0.0000 0.0000 0.6262(12) 0.075(12) Uani 0.30 3 d SP . . 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 0.02309(11) 0.02309(11) 0.01570(13) 0.000 0.000 0.01155(5) O9 0.036(3) 0.034(3) 0.086(4) 0.010(3) 0.016(3) 0.015(2) N3 0.055(4) 0.046(3) 0.042(3) 0.019(3) 0.009(3) 0.030(3) N6 0.031(3) 0.050(3) 0.047(3) -0.009(3) 0.009(2) 0.022(3) N9 0.057(4) 0.073(5) 0.037(3) 0.001(3) 0.011(3) 0.041(4) N28 0.059(6) 0.055(5) 0.022(4) -0.011(3) -0.004(3) 0.041(5) C1 0.043(4) 0.061(5) 0.047(4) -0.003(3) 0.019(3) 0.028(4) C2 0.044(4) 0.053(4) 0.042(4) -0.005(3) 0.016(3) 0.026(3) C4 0.049(4) 0.040(4) 0.040(4) 0.019(3) 0.011(3) 0.025(3) C5 0.051(4) 0.028(3) 0.051(4) 0.018(3) 0.011(3) 0.021(3) C7 0.051(4) 0.035(4) 0.058(4) 0.010(3) 0.009(3) 0.026(3) C9 0.050(4) 0.037(3) 0.049(4) 0.020(3) 0.024(3) 0.025(3) C10 0.063(5) 0.064(5) 0.055(5) -0.007(4) 0.030(4) 0.026(4) C11 0.121(10) 0.073(7) 0.076(7) 0.014(6) 0.076(8) 0.036(7) C12 0.063(6) 0.096(8) 0.092(8) -0.023(6) 0.036(6) 0.040(6) C20 0.027(3) 0.049(4) 0.055(4) -0.008(3) 0.008(3) 0.016(3) C21 0.029(3) 0.029(3) 0.045(4) 0.002(3) 0.006(3) 0.014(3) C22 0.027(3) 0.025(3) 0.028(3) -0.003(2) -0.002(2) 0.011(2) C23 0.019(4) 0.033(5) 0.041(5) -0.001(4) -0.004(3) 0.019(4) C24 0.032(3) 0.034(3) 0.041(3) -0.003(3) -0.010(3) 0.021(3) C25 0.027(3) 0.026(3) 0.065(5) -0.006(3) -0.013(3) 0.010(2) C26 0.021(3) 0.034(4) 0.060(5) 0.003(3) 0.004(3) 0.012(3) C27 0.037(4) 0.044(4) 0.046(4) -0.015(3) -0.017(3) 0.026(3) C29 0.058(5) 0.078(6) 0.037(4) -0.026(4) -0.012(3) 0.044(5) C30 0.072(6) 0.092(7) 0.071(6) -0.048(6) -0.022(5) 0.059(6) C31 0.053(6) 0.095(10) 0.109(10) -0.079(8) -0.049(6) 0.046(6) C32 0.042(4) 0.059(5) 0.087(7) -0.039(5) -0.025(4) 0.031(4) O51 0.045(4) 0.044(4) 0.050(4) -0.010(3) 0.009(3) 0.011(3) O52 0.049(5) 0.059(7) 0.140(12) 0.044(7) 0.033(7) 0.039(5) O53 0.056(9) 0.052(9) 0.042(8) -0.002(7) -0.006(7) 0.027(8) O54 0.042(8) 0.070(10) 0.045(8) -0.006(7) 0.001(6) 0.037(8) O55 0.11(2) 0.11(2) 0.009(12) 0.000 0.000 0.054(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 C23 2.008(10) 2_655 ? Ir1 C23 2.008(10) 3_665 ? Ir1 C23 2.008(10) . ? Ir1 N28 2.103(10) 2_655 ? Ir1 N28 2.103(10) . ? Ir1 N28 2.103(10) 3_665 ? O9 C9 1.233(10) . ? N3 C2 1.336(10) 2_655 ? N3 C4 1.387(10) . ? N6 C2 1.372(11) . ? N6 C5 1.373(10) 3_665 ? N6 C20 1.475(10) . ? N9 C9 1.336(10) . ? N9 C1 1.461(11) . ? N9 H9 0.8800 . ? N28 C29 1.355(11) . ? N28 C27 1.361(13) . ? C1 C2 1.477(11) . ? C1 C10 1.524(10) . ? C1 H1 1.0000 . ? C2 N3 1.336(10) 3_665 ? C4 C5 1.388(11) . ? C4 C9 1.477(10) . ? C5 N6 1.373(10) 2_655 ? C5 C7 1.464(12) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C10 C11 1.532(14) . ? C10 C12 1.557(17) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C20 C21 1.529(10) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C26 1.385(10) . ? C21 C22 1.387(9) . ? C22 C23 1.399(12) . ? C22 H22 0.9500 . ? C23 C24 1.432(12) . ? C24 C25 1.393(10) . ? C24 C27 1.471(10) . ? C25 C26 1.366(12) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.389(10) . ? C29 C30 1.374(12) . ? C29 H29 0.9500 . ? C30 C31 1.376(18) . ? C30 H30 0.9500 . ? C31 C32 1.391(15) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 Ir1 C23 99.2(4) 2_655 3_665 ? C23 Ir1 C23 99.2(4) 2_655 . ? C23 Ir1 C23 99.2(4) 3_665 . ? C23 Ir1 N28 79.9(4) 2_655 2_655 ? C23 Ir1 N28 84.6(4) 3_665 2_655 ? C23 Ir1 N28 176.2(6) . 2_655 ? C23 Ir1 N28 84.6(4) 2_655 . ? C23 Ir1 N28 176.2(6) 3_665 . ? C23 Ir1 N28 79.9(4) . . ? N28 Ir1 N28 96.3(4) 2_655 . ? C23 Ir1 N28 176.2(6) 2_655 3_665 ? C23 Ir1 N28 79.9(4) 3_665 3_665 ? C23 Ir1 N28 84.6(4) . 3_665 ? N28 Ir1 N28 96.3(4) 2_655 3_665 ? N28 Ir1 N28 96.3(4) . 3_665 ? C2 N3 C4 105.0(7) 2_655 . ? C2 N6 C5 108.8(7) . 3_665 ? C2 N6 C20 124.7(7) . . ? C5 N6 C20 123.7(7) 3_665 . ? C9 N9 C1 122.2(7) . . ? C9 N9 H9 118.9 . . ? C1 N9 H9 118.9 . . ? C29 N28 C27 118.9(9) . . ? C29 N28 Ir1 125.5(8) . . ? C27 N28 Ir1 115.6(6) . . ? N9 C1 C2 108.2(6) . . ? N9 C1 C10 113.0(8) . . ? C2 C1 C10 113.5(7) . . ? N9 C1 H1 107.3 . . ? C2 C1 H1 107.3 . . ? C10 C1 H1 107.3 . . ? N3 C2 N6 110.7(7) 3_665 . ? N3 C2 C1 124.0(8) 3_665 . ? N6 C2 C1 125.3(7) . . ? N3 C4 C5 111.1(7) . . ? N3 C4 C9 121.0(7) . . ? C5 C4 C9 126.6(8) . . ? N6 C5 C4 104.3(7) 2_655 . ? N6 C5 C7 124.0(7) 2_655 . ? C4 C5 C7 131.7(7) . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O9 C9 N9 122.6(7) . . ? O9 C9 C4 122.5(7) . . ? N9 C9 C4 114.8(8) . . ? C1 C10 C11 111.7(8) . . ? C1 C10 C12 106.6(9) . . ? C11 C10 C12 111.7(10) . . ? C1 C10 H10 108.9 . . ? C11 C10 H10 108.9 . . ? C12 C10 H10 108.9 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N6 C20 C21 112.3(6) . . ? N6 C20 H20A 109.1 . . ? C21 C20 H20A 109.1 . . ? N6 C20 H20B 109.1 . . ? C21 C20 H20B 109.1 . . ? H20A C20 H20B 107.9 . . ? C26 C21 C22 120.6(6) . . ? C26 C21 C20 118.1(6) . . ? C22 C21 C20 121.3(6) . . ? C21 C22 C23 122.0(6) . . ? C21 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? C22 C23 C24 115.3(8) . . ? C22 C23 Ir1 129.2(7) . . ? C24 C23 Ir1 114.9(7) . . ? C25 C24 C23 122.0(7) . . ? C25 C24 C27 122.3(6) . . ? C23 C24 C27 115.6(7) . . ? C26 C25 C24 120.1(6) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C21 119.7(6) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? N28 C27 C32 121.4(8) . . ? N28 C27 C24 113.8(7) . . ? C32 C27 C24 124.8(7) . . ? N28 C29 C30 122.0(10) . . ? N28 C29 H29 119.0 . . ? C30 C29 H29 119.0 . . ? C29 C30 C31 119.2(9) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? C30 C31 C32 120.0(9) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C27 C32 C31 118.5(10) . . ? C27 C32 H32 120.8 . . ? C31 C32 H32 120.8 . . ? 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 C23 Ir1 N28 C29 -81.2(11) 2_655 . . . ? C23 Ir1 N28 C29 101(8) 3_665 . . . ? C23 Ir1 N28 C29 178.4(10) . . . . ? N28 Ir1 N28 C29 -2.0(10) 2_655 . . . ? N28 Ir1 N28 C29 95.1(7) 3_665 . . . ? C23 Ir1 N28 C27 99.3(6) 2_655 . . . ? C23 Ir1 N28 C27 -78(8) 3_665 . . . ? C23 Ir1 N28 C27 -1.1(7) . . . . ? N28 Ir1 N28 C27 178.5(7) 2_655 . . . ? N28 Ir1 N28 C27 -84.4(10) 3_665 . . . ? C9 N9 C1 C2 -108.8(8) . . . . ? C9 N9 C1 C10 124.6(8) . . . . ? C5 N6 C2 N3 0.1(8) 3_665 . . 3_665 ? C20 N6 C2 N3 161.8(6) . . . 3_665 ? C5 N6 C2 C1 -179.8(6) 3_665 . . . ? C20 N6 C2 C1 -18.1(10) . . . . ? N9 C1 C2 N3 -57.3(9) . . . 3_665 ? C10 C1 C2 N3 69.0(10) . . . 3_665 ? N9 C1 C2 N6 122.6(8) . . . . ? C10 C1 C2 N6 -111.1(9) . . . . ? C2 N3 C4 C5 0.2(7) 2_655 . . . ? C2 N3 C4 C9 -167.8(6) 2_655 . . . ? N3 C4 C5 N6 -0.1(7) . . . 2_655 ? C9 C4 C5 N6 167.0(6) . . . 2_655 ? N3 C4 C5 C7 179.7(7) . . . . ? C9 C4 C5 C7 -13.2(12) . . . . ? C1 N9 C9 O9 -18.2(11) . . . . ? C1 N9 C9 C4 161.0(6) . . . . ? N3 C4 C9 O9 -172.5(6) . . . . ? C5 C4 C9 O9 21.5(11) . . . . ? N3 C4 C9 N9 8.3(9) . . . . ? C5 C4 C9 N9 -157.7(7) . . . . ? N9 C1 C10 C11 -49.3(13) . . . . ? C2 C1 C10 C11 -172.9(10) . . . . ? N9 C1 C10 C12 -171.4(8) . . . . ? C2 C1 C10 C12 64.9(11) . . . . ? C2 N6 C20 C21 -76.5(8) . . . . ? C5 N6 C20 C21 82.6(9) 3_665 . . . ? N6 C20 C21 C26 147.3(7) . . . . ? N6 C20 C21 C22 -34.8(10) . . . . ? C26 C21 C22 C23 6.9(11) . . . . ? C20 C21 C22 C23 -171.0(8) . . . . ? C21 C22 C23 C24 -5.2(12) . . . . ? C21 C22 C23 Ir1 165.1(6) . . . . ? C23 Ir1 C23 C22 104.6(5) 2_655 . . . ? C23 Ir1 C23 C22 3.6(10) 3_665 . . . ? N28 Ir1 C23 C22 -179(100) 2_655 . . . ? N28 Ir1 C23 C22 -172.7(9) . . . . ? N28 Ir1 C23 C22 -75.3(10) 3_665 . . . ? C23 Ir1 C23 C24 -85.1(9) 2_655 . . . ? C23 Ir1 C23 C24 174.0(6) 3_665 . . . ? N28 Ir1 C23 C24 -8(8) 2_655 . . . ? N28 Ir1 C23 C24 -2.3(6) . . . . ? N28 Ir1 C23 C24 95.1(5) 3_665 . . . ? C22 C23 C24 C25 0.8(12) . . . . ? Ir1 C23 C24 C25 -170.9(5) . . . . ? C22 C23 C24 C27 176.9(7) . . . . ? Ir1 C23 C24 C27 5.2(9) . . . . ? C23 C24 C25 C26 1.9(11) . . . . ? C27 C24 C25 C26 -173.9(7) . . . . ? C24 C25 C26 C21 -0.5(12) . . . . ? C22 C21 C26 C25 -3.8(12) . . . . ? C20 C21 C26 C25 174.1(7) . . . . ? C29 N28 C27 C32 3.0(14) . . . . ? Ir1 N28 C27 C32 -177.4(7) . . . . ? C29 N28 C27 C24 -175.5(8) . . . . ? Ir1 N28 C27 C24 4.0(10) . . . . ? C25 C24 C27 N28 170.1(7) . . . . ? C23 C24 C27 N28 -6.0(10) . . . . ? C25 C24 C27 C32 -8.4(11) . . . . ? C23 C24 C27 C32 175.5(8) . . . . ? C27 N28 C29 C30 -0.9(15) . . . . ? Ir1 N28 C29 C30 179.7(8) . . . . ? N28 C29 C30 C31 -0.4(16) . . . . ? C29 C30 C31 C32 -1(2) . . . . ? N28 C27 C32 C31 -3.9(15) . . . . ? C24 C27 C32 C31 174.4(10) . . . . ? C30 C31 C32 C27 2.6(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.718 _refine_diff_density_min -0.728 _refine_diff_density_rms 0.143 #========================================================================== data_gh37 _database_code_depnum_ccdc_archive 'CCDC 257960' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'in paper 3d' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C53 H64 Cl4 N10 O3' _chemical_formula_weight 1030.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.0619(2) _cell_length_b 15.4301(3) _cell_length_c 13.67510(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.0570(10) _cell_angle_gamma 90.00 _cell_volume 2754.39(7) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9294 _exptl_absorpt_correction_T_max 0.9689 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16688 _diffrn_reflns_av_R_equivalents 0.0966 _diffrn_reflns_av_sigmaI/netI 0.1140 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 21.50 _reflns_number_total 6327 _reflns_number_gt 4978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0751P)^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 noref _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 0.08(9) _refine_ls_number_reflns 6327 _refine_ls_number_parameters 640 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1625 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 N1 N 0.4036(3) 1.2601(3) 0.4034(3) 0.0332(12) Uani 1 1 d . . . C11 C 0.3491(4) 1.2581(4) -0.0364(4) 0.0358(14) Uani 1 1 d . . . H11 H 0.4223 1.2389 -0.0354 0.043 Uiso 1 1 calc R . . C12 C 0.3413(4) 1.3392(3) 0.0240(4) 0.0292(14) Uani 1 1 d . . . N13 N 0.2536(4) 1.3684(3) 0.0568(3) 0.0354(12) Uani 1 1 d . . . C14 C 0.2796(5) 1.4429(4) 0.1109(4) 0.0353(15) Uani 1 1 d . . . C15 C 0.3814(5) 1.4573(4) 0.1096(4) 0.0427(16) Uani 1 1 d . . . N16 N 0.4214(3) 1.3910(3) 0.0546(3) 0.0348(12) Uani 1 1 d . . . C17 C 0.5306(4) 1.3714(5) 0.0505(4) 0.0479(18) Uani 1 1 d . . . H17A H 0.5686 1.4260 0.0400 0.057 Uiso 1 1 calc R . . H17B H 0.5418 1.3331 -0.0062 0.057 Uiso 1 1 calc R . . C18 C 0.4495(5) 1.5253(5) 0.1576(5) 0.062(2) Uani 1 1 d . . . H18A H 0.4088 1.5616 0.2004 0.093 Uiso 1 1 calc R . . H18B H 0.4794 1.5615 0.1072 0.093 Uiso 1 1 calc R . . H18C H 0.5044 1.4970 0.1965 0.093 Uiso 1 1 calc R . . C19 C 0.2011(5) 1.4881(4) 0.1649(4) 0.0369(15) Uani 1 1 d . . . O19 O 0.2170(4) 1.5574(3) 0.2056(4) 0.0642(14) Uani 1 1 d . . . N19 N 0.2882(4) 1.1914(3) 0.0102(3) 0.0374(12) Uani 1 1 d . . . H19 H 0.2213 1.1981 0.0118 0.045 Uiso 1 1 calc R . . C20 C 0.5736(4) 1.3281(4) 0.1420(4) 0.0385(16) Uani 1 1 d . . . C21 C 0.5133(4) 1.2878(4) 0.2091(4) 0.0350(15) Uani 1 1 d . . . H21 H 0.4413 1.2859 0.1969 0.042 Uiso 1 1 calc R . . C22 C 0.5545(4) 1.2495(4) 0.2943(4) 0.0370(15) Uani 1 1 d . . . C23 C 0.6605(5) 1.2522(4) 0.3091(5) 0.0449(16) Uani 1 1 d . . . H23 H 0.6909 1.2275 0.3667 0.054 Uiso 1 1 calc R . . C24 C 0.7218(5) 1.2901(4) 0.2416(5) 0.0512(18) Uani 1 1 d . . . H24 H 0.7941 1.2887 0.2514 0.061 Uiso 1 1 calc R . . C25 C 0.6792(5) 1.3301(5) 0.1600(5) 0.0531(19) Uani 1 1 d . . . H25 H 0.7220 1.3591 0.1157 0.064 Uiso 1 1 calc R . . C26 C 0.4897(4) 1.2072(4) 0.3689(4) 0.0410(16) Uani 1 1 d . . . H26A H 0.4614 1.1528 0.3406 0.049 Uiso 1 1 calc R . . H26B H 0.5342 1.1914 0.4262 0.049 Uiso 1 1 calc R . . C27 C 0.3128(5) 1.2737(4) -0.1435(4) 0.0433(17) Uani 1 1 d . . . H27 H 0.2391 1.2913 -0.1432 0.052 Uiso 1 1 calc R . . C28 C 0.3192(6) 1.1955(5) -0.2033(5) 0.070(2) Uani 1 1 d . . . H28A H 0.3913 1.1791 -0.2092 0.104 Uiso 1 1 calc R . . H28B H 0.2885 1.2067 -0.2685 0.104 Uiso 1 1 calc R . . H28C H 0.2823 1.1482 -0.1723 0.104 Uiso 1 1 calc R . . C29 C 0.3729(6) 1.3487(5) -0.1898(5) 0.059(2) Uani 1 1 d . . . H29A H 0.4445 1.3313 -0.1964 0.089 Uiso 1 1 calc R . . H29B H 0.3699 1.4001 -0.1479 0.089 Uiso 1 1 calc R . . H29C H 0.3425 1.3622 -0.2546 0.089 Uiso 1 1 calc R . . C31 C 0.0354(4) 1.4694(4) 0.2402(4) 0.0372(15) Uani 1 1 d . . . H31 H 0.0610 1.5199 0.2798 0.045 Uiso 1 1 calc R . . C32 C 0.0286(4) 1.3924(4) 0.3065(4) 0.0328(14) Uani 1 1 d . . . N33 N 0.0098(4) 1.3141(3) 0.2776(4) 0.0365(12) Uani 1 1 d . . . C34 C 0.0159(4) 1.2611(4) 0.3601(4) 0.0350(15) Uani 1 1 d . . . C35 C 0.0381(4) 1.3098(4) 0.4410(4) 0.0367(15) Uani 1 1 d . . . N36 N 0.0457(3) 1.3943(3) 0.4068(4) 0.0376(12) Uani 1 1 d . . . C37 C 0.0819(4) 1.4684(4) 0.4667(4) 0.0405(15) Uani 1 1 d . . . H37A H 0.0425 1.4704 0.5272 0.049 Uiso 1 1 calc R . . H37B H 0.0678 1.5226 0.4299 0.049 Uiso 1 1 calc R . . C38 C 0.0573(5) 1.2865(4) 0.5455(4) 0.0506(18) Uani 1 1 d . . . H38A H 0.0472 1.2241 0.5540 0.076 Uiso 1 1 calc R . . H38B H 0.0096 1.3183 0.5860 0.076 Uiso 1 1 calc R . . H38C H 0.1279 1.3018 0.5653 0.076 Uiso 1 1 calc R . . C39 C 0.0085(4) 1.1672(4) 0.3493(5) 0.0353(15) Uani 1 1 d . . . O39 O 0.0209(4) 1.1169(3) 0.4184(3) 0.0517(12) Uani 1 1 d . . . N39 N 0.1100(4) 1.4493(3) 0.1677(4) 0.0395(12) Uani 1 1 d . . . H39 H 0.0945 1.4096 0.1234 0.047 Uiso 1 1 calc R . . C40 C 0.1931(4) 1.4647(3) 0.4941(4) 0.0307(14) Uani 1 1 d . . . C41 C 0.2614(4) 1.4113(4) 0.4462(4) 0.0335(14) Uani 1 1 d . . . H41 H 0.2374 1.3775 0.3921 0.040 Uiso 1 1 calc R . . C42 C 0.3647(5) 1.4065(3) 0.4766(4) 0.0356(15) Uani 1 1 d . . . C43 C 0.3987(5) 1.4577(4) 0.5557(4) 0.0394(15) Uani 1 1 d . . . H43 H 0.4683 1.4548 0.5781 0.047 Uiso 1 1 calc R . . C44 C 0.3317(5) 1.5123(4) 0.6013(4) 0.0411(16) Uani 1 1 d . . . H44 H 0.3561 1.5482 0.6535 0.049 Uiso 1 1 calc R . . C45 C 0.2301(5) 1.5151(4) 0.5719(4) 0.0361(15) Uani 1 1 d . . . H45 H 0.1846 1.5519 0.6051 0.043 Uiso 1 1 calc R . . C46 C 0.4402(4) 1.3473(4) 0.4274(5) 0.0375(15) Uani 1 1 d . . . H46A H 0.4611 1.3755 0.3662 0.045 Uiso 1 1 calc R . . H46B H 0.5022 1.3420 0.4708 0.045 Uiso 1 1 calc R . . C47 C -0.0703(5) 1.4932(5) 0.1933(5) 0.0543(19) Uani 1 1 d . . . H47 H -0.0947 1.4426 0.1530 0.065 Uiso 1 1 calc R . . C48 C -0.0636(6) 1.5697(6) 0.1265(6) 0.082(3) Uani 1 1 d . . . H48A H -0.1298 1.5785 0.0919 0.123 Uiso 1 1 calc R . . H48B H -0.0107 1.5592 0.0789 0.123 Uiso 1 1 calc R . . H48C H -0.0459 1.6215 0.1650 0.123 Uiso 1 1 calc R . . C49 C -0.1465(5) 1.5079(6) 0.2718(6) 0.070(2) Uani 1 1 d . . . H49A H -0.1286 1.5609 0.3079 0.105 Uiso 1 1 calc R . . H49B H -0.1451 1.4585 0.3168 0.105 Uiso 1 1 calc R . . H49C H -0.2153 1.5138 0.2416 0.105 Uiso 1 1 calc R . . C51 C 0.0152(4) 1.0528(4) 0.2251(4) 0.0366(15) Uani 1 1 d . . . H51 H 0.0073 1.0132 0.2822 0.044 Uiso 1 1 calc R . . C52 C 0.1278(5) 1.0508(4) 0.1960(4) 0.0338(15) Uani 1 1 d . . . N53 N 0.1609(3) 1.0964(3) 0.1247(3) 0.0337(12) Uani 1 1 d . . . C54 C 0.2636(4) 1.0753(3) 0.1186(4) 0.0304(14) Uani 1 1 d . . . C55 C 0.2895(4) 1.0153(3) 0.1876(4) 0.0344(15) Uani 1 1 d . . . N56 N 0.2026(4) 1.0009(3) 0.2402(3) 0.0355(12) Uani 1 1 d . . . C57 C 0.1987(5) 0.9534(4) 0.3321(4) 0.0453(16) Uani 1 1 d . . . H57A H 0.2261 0.8943 0.3227 0.054 Uiso 1 1 calc R . . H57B H 0.1264 0.9478 0.3506 0.054 Uiso 1 1 calc R . . C58 C 0.3896(5) 0.9740(4) 0.2146(5) 0.0580(19) Uani 1 1 d . . . H58A H 0.4373 0.9829 0.1618 0.087 Uiso 1 1 calc R . . H58B H 0.3795 0.9118 0.2248 0.087 Uiso 1 1 calc R . . H58C H 0.4179 1.0002 0.2750 0.087 Uiso 1 1 calc R . . C59 C 0.3312(5) 1.1202(4) 0.0508(4) 0.0375(15) Uani 1 1 d . . . O59 O 0.4174(3) 1.0957(3) 0.0360(3) 0.0545(13) Uani 1 1 d . . . N59 N -0.0077(4) 1.1403(3) 0.2555(4) 0.0391(13) Uani 1 1 d . . . H59 H -0.0330 1.1772 0.2119 0.047 Uiso 1 1 calc R . . C60 C 0.2593(4) 0.9971(4) 0.4148(4) 0.0341(14) Uani 1 1 d . . . C61 C 0.2825(5) 1.0875(4) 0.4138(5) 0.0414(16) Uani 1 1 d . . . H61 H 0.2582 1.1225 0.3607 0.050 Uiso 1 1 calc R . . C62 C 0.3399(4) 1.1243(4) 0.4896(4) 0.0345(15) Uani 1 1 d . . . C63 C 0.3716(4) 1.0734(4) 0.5684(4) 0.0355(15) Uani 1 1 d . . . H63 H 0.4113 1.0987 0.6204 0.043 Uiso 1 1 calc R . . C64 C 0.3466(5) 0.9869(4) 0.5728(4) 0.0391(16) Uani 1 1 d . . . H64 H 0.3677 0.9529 0.6279 0.047 Uiso 1 1 calc R . . C65 C 0.2889(5) 0.9490(4) 0.4937(4) 0.0394(16) Uani 1 1 d . . . H65 H 0.2710 0.8894 0.4961 0.047 Uiso 1 1 calc R . . C66 C 0.3618(5) 1.2213(4) 0.4935(4) 0.0404(15) Uani 1 1 d . . . H66A H 0.2973 1.2517 0.5080 0.048 Uiso 1 1 calc R . . H66B H 0.4110 1.2325 0.5488 0.048 Uiso 1 1 calc R . . C67 C -0.0553(5) 1.0216(4) 0.1414(4) 0.0412(16) Uani 1 1 d . . . H67 H -0.0443 1.0603 0.0840 0.049 Uiso 1 1 calc R . . C68 C -0.1663(5) 1.0278(5) 0.1653(5) 0.061(2) Uani 1 1 d . . . H68A H -0.2088 1.0078 0.1093 0.092 Uiso 1 1 calc R . . H68B H -0.1833 1.0881 0.1801 0.092 Uiso 1 1 calc R . . H68C H -0.1792 0.9914 0.2224 0.092 Uiso 1 1 calc R . . C69 C -0.0254(6) 0.9308(4) 0.1122(6) 0.066(2) Uani 1 1 d . . . H69A H -0.0207 0.8939 0.1705 0.100 Uiso 1 1 calc R . . H69B H 0.0411 0.9323 0.0813 0.100 Uiso 1 1 calc R . . H69C H -0.0773 0.9074 0.0658 0.100 Uiso 1 1 calc R . . C81 C 0.1891(10) 0.7085(7) 0.0419(9) 0.136(5) Uani 1 1 d . . . H81A H 0.2388 0.6818 -0.0020 0.163 Uiso 1 1 calc R . . H81B H 0.1663 0.6639 0.0884 0.163 Uiso 1 1 calc R . . Cl1 Cl 0.2453(3) 0.7964(3) 0.1054(2) 0.1440(13) Uani 1 1 d . . . Cl2 Cl 0.0839(2) 0.75012(18) -0.0263(2) 0.1198(10) Uani 1 1 d . . . C82 C -0.3054(6) 1.1603(4) 0.6202(5) 0.060(2) Uani 1 1 d . . . H82A H -0.3405 1.1246 0.5690 0.072 Uiso 1 1 calc R . . H82B H -0.2864 1.1218 0.6758 0.072 Uiso 1 1 calc R . . Cl3 Cl -0.19369(17) 1.20490(13) 0.57313(18) 0.0819(7) Uani 1 1 d . . . Cl4 Cl -0.38939(15) 1.23938(14) 0.65952(17) 0.0799(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 N1 0.043(3) 0.020(2) 0.037(3) 0.001(2) 0.009(2) -0.002(2) C11 0.035(3) 0.035(3) 0.038(4) -0.001(3) 0.006(3) -0.004(3) C12 0.036(4) 0.027(3) 0.025(3) 0.009(3) 0.004(3) -0.004(3) N13 0.038(3) 0.034(3) 0.035(3) -0.001(2) 0.004(2) 0.002(2) C14 0.040(4) 0.034(4) 0.033(3) -0.003(3) 0.006(3) -0.004(3) C15 0.048(4) 0.044(4) 0.036(4) -0.005(3) 0.011(3) -0.013(3) N16 0.032(3) 0.043(3) 0.031(3) -0.003(2) 0.005(2) -0.008(3) C17 0.031(4) 0.069(5) 0.045(4) -0.004(4) 0.016(3) -0.010(3) C18 0.058(5) 0.065(5) 0.065(5) -0.019(4) 0.017(4) -0.025(4) C19 0.046(4) 0.026(4) 0.039(4) -0.001(3) 0.003(3) -0.010(3) O19 0.066(3) 0.050(3) 0.079(4) -0.020(3) 0.027(3) -0.014(2) N19 0.036(3) 0.031(3) 0.047(3) 0.009(2) 0.011(2) -0.004(2) C20 0.037(4) 0.047(4) 0.031(4) -0.005(3) 0.004(3) -0.005(3) C21 0.028(3) 0.038(3) 0.039(4) -0.007(3) 0.003(3) -0.006(3) C22 0.038(4) 0.032(3) 0.042(4) -0.005(3) 0.002(3) 0.008(3) C23 0.042(4) 0.047(4) 0.046(4) -0.007(3) -0.001(3) 0.005(3) C24 0.032(4) 0.066(5) 0.056(5) 0.000(4) -0.002(4) -0.003(3) C25 0.032(4) 0.064(5) 0.065(5) -0.009(4) 0.021(4) -0.008(3) C26 0.038(3) 0.041(4) 0.044(4) 0.006(3) 0.006(3) 0.010(3) C27 0.049(4) 0.050(4) 0.032(4) 0.002(3) 0.019(3) -0.009(3) C28 0.097(6) 0.055(4) 0.058(5) -0.014(4) 0.025(4) -0.014(4) C29 0.078(5) 0.065(5) 0.035(4) 0.004(3) 0.011(4) -0.012(4) C31 0.042(4) 0.030(3) 0.041(4) -0.003(3) 0.010(3) 0.009(3) C32 0.031(3) 0.039(4) 0.028(4) -0.003(3) 0.004(3) 0.005(3) N33 0.034(3) 0.036(3) 0.040(3) -0.006(3) 0.003(2) -0.005(2) C34 0.034(3) 0.039(4) 0.033(4) 0.005(3) 0.008(3) -0.002(3) C35 0.039(4) 0.038(4) 0.034(4) -0.002(3) 0.011(3) -0.007(3) N36 0.037(3) 0.032(3) 0.044(4) -0.008(3) 0.011(2) -0.002(2) C37 0.049(4) 0.041(4) 0.032(3) -0.015(3) 0.000(3) 0.001(3) C38 0.068(5) 0.054(4) 0.030(4) -0.002(3) 0.011(3) -0.006(4) C39 0.036(4) 0.033(4) 0.037(4) 0.003(3) 0.018(3) -0.007(3) O39 0.079(3) 0.039(3) 0.038(3) 0.004(2) 0.016(2) -0.016(2) N39 0.041(3) 0.031(3) 0.047(3) -0.011(2) 0.007(3) 0.002(3) C40 0.043(4) 0.025(3) 0.025(3) -0.003(3) 0.008(3) -0.005(3) C41 0.042(4) 0.029(3) 0.030(3) -0.001(3) 0.002(3) -0.003(3) C42 0.042(4) 0.025(3) 0.040(4) 0.003(3) 0.015(3) -0.006(3) C43 0.045(4) 0.035(3) 0.039(4) -0.004(3) 0.006(3) -0.008(3) C44 0.059(5) 0.036(4) 0.029(3) -0.008(3) 0.005(3) -0.011(3) C45 0.050(4) 0.029(3) 0.030(4) -0.004(3) 0.012(3) 0.003(3) C46 0.038(4) 0.033(3) 0.042(4) -0.003(3) 0.008(3) -0.003(3) C47 0.057(5) 0.050(4) 0.058(5) 0.015(4) 0.016(4) 0.018(4) C48 0.076(6) 0.090(6) 0.081(6) 0.025(5) 0.021(5) 0.034(5) C49 0.043(4) 0.093(6) 0.075(5) 0.017(5) 0.025(4) 0.030(4) C51 0.045(4) 0.031(3) 0.034(4) -0.003(3) 0.007(3) -0.003(3) C52 0.040(4) 0.024(3) 0.038(4) -0.002(3) -0.006(3) -0.005(3) N53 0.037(3) 0.031(3) 0.033(3) 0.011(2) 0.010(2) -0.005(2) C54 0.037(4) 0.020(3) 0.034(4) -0.001(3) 0.001(3) -0.008(3) C55 0.041(4) 0.023(3) 0.039(4) -0.006(3) 0.004(3) 0.003(3) N56 0.052(3) 0.023(3) 0.032(3) 0.002(2) -0.003(3) -0.010(3) C57 0.053(4) 0.033(3) 0.050(4) 0.010(3) -0.004(3) -0.005(3) C58 0.063(5) 0.041(4) 0.070(5) 0.005(4) -0.002(4) 0.008(4) C59 0.044(4) 0.031(4) 0.038(4) -0.006(3) 0.006(3) 0.005(3) O59 0.049(3) 0.048(3) 0.068(3) 0.011(2) 0.025(2) 0.014(2) N59 0.045(3) 0.035(3) 0.036(3) 0.000(2) -0.010(2) 0.002(2) C60 0.039(3) 0.028(3) 0.036(4) 0.001(3) 0.008(3) -0.004(3) C61 0.050(4) 0.033(4) 0.041(4) 0.008(3) 0.008(3) 0.005(3) C62 0.035(4) 0.038(4) 0.031(4) -0.004(3) 0.007(3) -0.002(3) C63 0.041(4) 0.039(4) 0.026(4) 0.000(3) 0.009(3) 0.009(3) C64 0.051(4) 0.034(4) 0.033(4) 0.006(3) 0.008(3) 0.014(3) C65 0.044(4) 0.033(3) 0.042(4) 0.015(3) 0.014(3) 0.008(3) C66 0.056(4) 0.034(4) 0.032(3) -0.002(3) 0.009(3) 0.001(3) C67 0.051(4) 0.045(4) 0.027(3) -0.008(3) 0.004(3) -0.020(3) C68 0.047(4) 0.079(5) 0.058(5) -0.013(4) 0.007(4) -0.019(4) C69 0.082(5) 0.051(5) 0.066(5) -0.021(4) -0.003(4) -0.021(4) C81 0.220(14) 0.082(7) 0.102(8) 0.015(6) -0.048(9) -0.029(8) Cl1 0.160(3) 0.183(3) 0.089(2) -0.028(2) 0.0040(19) -0.068(2) Cl2 0.156(3) 0.0867(17) 0.115(2) -0.0274(17) -0.0159(18) 0.0001(18) C82 0.077(5) 0.049(4) 0.054(5) 0.001(4) 0.012(4) 0.007(4) Cl3 0.0763(13) 0.0571(12) 0.1138(17) -0.0071(12) 0.0240(12) -0.0021(10) Cl4 0.0691(13) 0.0706(13) 0.1000(16) -0.0220(12) 0.0043(11) 0.0074(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C46 1.461(7) . ? N1 C26 1.480(7) . ? N1 C66 1.492(7) . ? C11 N19 1.461(7) . ? C11 C12 1.506(8) . ? C11 C27 1.542(8) . ? C12 N13 1.324(7) . ? C12 N16 1.370(7) . ? N13 C14 1.403(7) . ? C14 C15 1.349(8) . ? C14 C19 1.461(9) . ? C15 N16 1.384(8) . ? C15 C18 1.510(9) . ? N16 C17 1.462(7) . ? C17 C20 1.508(9) . ? C19 O19 1.221(7) . ? C19 N39 1.333(8) . ? N19 C59 1.345(8) . ? C20 C21 1.379(8) . ? C20 C25 1.394(9) . ? C21 C22 1.396(8) . ? C22 C23 1.393(8) . ? C22 C26 1.499(8) . ? C23 C24 1.374(9) . ? C24 C25 1.375(10) . ? C27 C28 1.462(9) . ? C27 C29 1.547(9) . ? C31 N39 1.449(7) . ? C31 C32 1.499(8) . ? C31 C47 1.546(9) . ? C32 N33 1.291(7) . ? C32 N36 1.383(7) . ? N33 C34 1.393(7) . ? C34 C35 1.361(8) . ? C34 C39 1.459(8) . ? C35 N36 1.390(7) . ? C35 C38 1.485(8) . ? N36 C37 1.474(7) . ? C37 C40 1.488(8) . ? C39 O39 1.229(7) . ? C39 N59 1.357(8) . ? C40 C45 1.390(8) . ? C40 C41 1.395(8) . ? C41 C42 1.399(8) . ? C42 C43 1.398(8) . ? C42 C46 1.519(8) . ? C43 C44 1.379(8) . ? C44 C45 1.374(9) . ? C47 C48 1.497(10) . ? C47 C49 1.506(9) . ? C51 N59 1.447(7) . ? C51 C67 1.522(8) . ? C51 C52 1.538(9) . ? C52 N53 1.289(7) . ? C52 N56 1.367(7) . ? N53 C54 1.386(7) . ? C54 C55 1.357(8) . ? C54 C59 1.475(8) . ? C55 N56 1.384(7) . ? C55 C58 1.488(9) . ? N56 C57 1.458(7) . ? C57 C60 1.515(9) . ? C59 O59 1.212(7) . ? C60 C65 1.354(8) . ? C60 C61 1.428(8) . ? C61 C62 1.380(9) . ? C62 C63 1.384(8) . ? C62 C66 1.523(8) . ? C63 C64 1.376(8) . ? C64 C65 1.422(9) . ? C67 C68 1.500(9) . ? C67 C69 1.512(9) . ? C81 Cl2 1.754(12) . ? C81 Cl1 1.757(11) . ? C82 Cl4 1.739(7) . ? C82 Cl3 1.757(7) . ? 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 C46 N1 C26 109.5(4) . . ? C46 N1 C66 108.1(4) . . ? C26 N1 C66 110.3(4) . . ? N19 C11 C12 107.2(4) . . ? N19 C11 C27 111.8(5) . . ? C12 C11 C27 111.6(5) . . ? N13 C12 N16 111.1(5) . . ? N13 C12 C11 123.0(5) . . ? N16 C12 C11 125.9(5) . . ? C12 N13 C14 105.2(5) . . ? C15 C14 N13 110.3(5) . . ? C15 C14 C19 129.7(6) . . ? N13 C14 C19 119.8(5) . . ? C14 C15 N16 106.1(5) . . ? C14 C15 C18 132.4(6) . . ? N16 C15 C18 121.5(5) . . ? C12 N16 C15 107.4(4) . . ? C12 N16 C17 127.2(5) . . ? C15 N16 C17 124.1(5) . . ? N16 C17 C20 113.2(5) . . ? O19 C19 N39 121.1(6) . . ? O19 C19 C14 122.5(6) . . ? N39 C19 C14 116.4(5) . . ? C59 N19 C11 122.0(5) . . ? C21 C20 C25 118.5(6) . . ? C21 C20 C17 123.2(5) . . ? C25 C20 C17 118.3(5) . . ? C20 C21 C22 122.3(5) . . ? C23 C22 C21 117.3(5) . . ? C23 C22 C26 119.8(6) . . ? C21 C22 C26 122.9(5) . . ? C24 C23 C22 121.0(6) . . ? C23 C24 C25 120.5(6) . . ? C24 C25 C20 120.2(6) . . ? N1 C26 C22 115.5(5) . . ? C28 C27 C11 112.4(6) . . ? C28 C27 C29 110.4(5) . . ? C11 C27 C29 111.3(5) . . ? N39 C31 C32 107.4(4) . . ? N39 C31 C47 112.3(5) . . ? C32 C31 C47 111.6(5) . . ? N33 C32 N36 110.2(5) . . ? N33 C32 C31 124.9(5) . . ? N36 C32 C31 124.9(5) . . ? C32 N33 C34 107.3(5) . . ? C35 C34 N33 109.8(5) . . ? C35 C34 C39 130.0(6) . . ? N33 C34 C39 120.0(5) . . ? C34 C35 N36 105.1(5) . . ? C34 C35 C38 132.3(5) . . ? N36 C35 C38 122.6(5) . . ? C32 N36 C35 107.6(5) . . ? C32 N36 C37 127.2(5) . . ? C35 N36 C37 124.5(5) . . ? N36 C37 C40 113.6(5) . . ? O39 C39 N59 123.0(5) . . ? O39 C39 C34 122.9(6) . . ? N59 C39 C34 114.0(5) . . ? C19 N39 C31 123.1(5) . . ? C45 C40 C41 118.6(5) . . ? C45 C40 C37 118.7(5) . . ? C41 C40 C37 122.7(5) . . ? C40 C41 C42 121.2(5) . . ? C43 C42 C41 118.4(5) . . ? C43 C42 C46 119.3(5) . . ? C41 C42 C46 122.3(5) . . ? C44 C43 C42 120.4(6) . . ? C45 C44 C43 120.6(6) . . ? C44 C45 C40 120.8(5) . . ? N1 C46 C42 116.2(5) . . ? C48 C47 C49 111.8(6) . . ? C48 C47 C31 111.7(6) . . ? C49 C47 C31 110.0(6) . . ? N59 C51 C67 112.7(5) . . ? N59 C51 C52 107.6(4) . . ? C67 C51 C52 111.0(5) . . ? N53 C52 N56 112.8(5) . . ? N53 C52 C51 122.3(5) . . ? N56 C52 C51 124.8(5) . . ? C52 N53 C54 105.6(5) . . ? C55 C54 N53 109.7(5) . . ? C55 C54 C59 128.1(6) . . ? N53 C54 C59 122.0(5) . . ? C54 C55 N56 106.4(5) . . ? C54 C55 C58 131.3(6) . . ? N56 C55 C58 122.2(5) . . ? C52 N56 C55 105.4(5) . . ? C52 N56 C57 128.2(5) . . ? C55 N56 C57 125.7(5) . . ? N56 C57 C60 112.8(5) . . ? O59 C59 N19 124.2(6) . . ? O59 C59 C54 122.7(6) . . ? N19 C59 C54 113.1(5) . . ? C39 N59 C51 122.0(5) . . ? C65 C60 C61 119.3(6) . . ? C65 C60 C57 118.5(5) . . ? C61 C60 C57 122.2(5) . . ? C62 C61 C60 120.3(6) . . ? C61 C62 C63 119.3(6) . . ? C61 C62 C66 121.8(6) . . ? C63 C62 C66 118.7(5) . . ? C64 C63 C62 121.4(6) . . ? C63 C64 C65 119.0(6) . . ? C60 C65 C64 120.6(6) . . ? N1 C66 C62 116.0(5) . . ? C68 C67 C69 112.2(5) . . ? C68 C67 C51 112.3(5) . . ? C69 C67 C51 109.7(6) . . ? Cl2 C81 Cl1 106.6(6) . . ? Cl4 C82 Cl3 112.3(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 21.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.918 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.062