# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Paul Benny' _publ_contact_author_email BENNYP@WSU.EDU _publ_section_title ; "Click" Labeling Strategy for M(CO)3 (M= Re, 99mTc) Prostate Cancer Targeted Flutamide Agents ; loop_ _publ_author_name 'Paul Benny' 'Dejan-Kresimir Bucar' 'Leonard R MacGillivray' 'Adam L. Moore' # Attachment 'ccdc_deposit_Benny.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-07-23 at 17:24:22 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : mcg911 #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_5 _database_code_depnum_ccdc_archive 'CCDC 751744' #TrackingRef 'ccdc_deposit_Benny.cif' _audit_creation_date 2009-07-23T17:24:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C18 H15 N3 O3 Re), 2(CF3SO3), 3(CH2Cl2)' _chemical_formula_sum 'C41 H36 Cl6 F6 N6 O12 Re2 S2 ' _chemical_formula_weight 1567.98 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/m _symmetry_space_group_name_Hall '-C 2y' _cell_length_a 29.647(3) _cell_length_b 10.4289(11) _cell_length_c 8.1706(9) _cell_angle_alpha 90 _cell_angle_beta 100.620(5) _cell_angle_gamma 90 _cell_volume 2483.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 210(1) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _cell_measurement_reflns_used 5825 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 2.097 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1516.0 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.025 _exptl_crystal_size_min 0.02 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.443 _exptl_absorpt_correction_T_max 0.896 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 210(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_unetI/netI 0.0281 _diffrn_reflns_number 8477 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 2318 _reflns_number_gt 2042 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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 structure refinement was challenging owing to highly disordered solvent molecules. Fourier recycling suggested the presence of CH2Cl2 molecules in the structure. Despite the use of restrains, no acceptable model for the disordered solvent molecules could be found. The well modeled part of the structure was therefore treated with the SQUEEZE option in PLATON. The solvent molecules were found to occupy 363.3 A3, or 14.6% of the unit cell. The electron count of 245 electrons per unit cell corresponds to approximately 6 CH2Cl2 molecules. The use of the SQUEEZE routine resulted in a checkCIF report containing a series of alerts: 1. level A: - differences in the calculated and reported molecular weight - differences in the calculated and reported density 2. level B: - presence of a solvent accessible void - mu(cif) with mu(calc) ratio differs from 1.0 3. level-C: - differences in the calculated and reported F000 value - differences in the calculated and reported formulas Besides the SQUEEZE-related alerts, checkCIF revealed additional level-C alerts: 4. level-C: "Occupancy 0.50 less than 1.0 for Sp.pos ." - the atoms sitting on special positions are disordered and have therefore occupancies less than 0.5. ; _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^)+(0.0779P)^2^+20.6986P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0012(3) _refine_ls_number_reflns 2318 _refine_ls_number_parameters 158 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.438 _refine_diff_density_min -2.021 _refine_diff_density_rms 0.16 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.231 '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' 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 C1 C 0.9382(3) 0.8681(9) -0.0263(10) 0.052(2) Uani 1 1 d . . . C2 C 0.9767(4) 1 0.2460(13) 0.052(3) Uani 1 2 d S . . C3 C 0.9035(3) 0.8197(9) 0.4057(10) 0.059(2) Uani 1 1 d . . . C4 C 0.8793(4) 0.7537(11) 0.5034(12) 0.073(3) Uani 1 1 d . . . C5 C 0.8322(4) 0.7340(11) 0.4466(13) 0.073(3) Uani 1 1 d . . . C6 C 0.8126(3) 0.7812(10) 0.2918(13) 0.066(2) Uani 1 1 d . . . C7 C 0.8392(2) 0.8445(7) 0.1969(10) 0.0471(18) Uani 1 1 d . . . C8 C 0.8212(3) 0.8837(8) 0.0223(10) 0.055(2) Uani 1 1 d . . . C9 C 0.8423(4) 1 -0.2113(14) 0.073(4) Uani 1 2 d S . . C10 C 0.7947(5) 1 -0.3086(17) 0.066(3) Uani 1 2 d S . . C11 C 0.7597(5) 1 -0.396(2) 0.082(5) Uani 1 2 d S . . C12A C 0.8638(5) 0.5 0.0189(16) 0.0603(7) Uani 0.5 2 d SPD . 1 C12B C 0.8705(5) 0.5 -0.0292(14) 0.0603(7) Uani 0.5 2 d SPD . 2 F1A F 0.8531(5) 0.5 0.1700(13) 0.0603(7) Uani 0.5 2 d SPD . 1 F1B F 0.8810(3) 0.5998(9) 0.0727(12) 0.0603(7) Uani 0.5 1 d PD . 2 F2A F 0.8883(3) 0.6043(8) 0.0007(12) 0.0603(7) Uani 0.5 1 d PD . 1 F2B F 0.8979(4) 0.5 -0.1412(16) 0.0603(7) Uani 0.5 2 d SPD . 2 H3 H 0.9346 0.8332 0.4443 0.071 Uiso 1 1 calc R . . H4 H 0.8936 0.722 0.6063 0.087 Uiso 1 1 calc R . . H5 H 0.8146 0.6903 0.5116 0.088 Uiso 1 1 calc R . . H6 H 0.7814 0.77 0.2519 0.08 Uiso 1 1 calc R . . H8A H 0.8253 0.8139 -0.052 0.066 Uiso 1 1 calc R . . H8B H 0.7885 0.9007 0.0095 0.066 Uiso 1 1 calc R . . H9A H 0.8582 1.0751 -0.2416 0.088 Uiso 0.5 1 calc PR . . H9B H 0.8582 0.9249 -0.2416 0.088 Uiso 0.5 1 calc PR . . H11 H 0.7313 1 -0.4664 0.099 Uiso 1 2 calc SR . . N1 N 0.8844(2) 0.8666(7) 0.2553(8) 0.0466(15) Uani 1 1 d . . . N2 N 0.8447(3) 1 -0.0250(11) 0.044(2) Uani 1 2 d S . . O1 O 0.9501(2) 0.7916(7) -0.1074(8) 0.0671(17) Uani 1 1 d . . . O2 O 1.0128(3) 1 0.3298(10) 0.065(2) Uani 1 2 d S . . O3A O 0.8284(5) 0.5 -0.2885(16) 0.0603(7) Uani 0.5 2 d SPD . 1 O3B O 0.7870(5) 0.5 0.0065(19) 0.0603(7) Uani 0.5 2 d SPD . 2 O4A O 0.7893(4) 0.6152(10) -0.1108(15) 0.0603(7) Uani 0.5 1 d PD . 1 O4B O 0.8040(4) 0.6152(10) -0.2182(14) 0.0603(7) Uani 0.5 1 d PD . 2 Re1 Re 0.917050(13) 1 0.10963(5) 0.0445(2) Uani 1 2 d S . . S1A S 0.8112(3) 0.5 -0.1365(14) 0.0603(7) Uani 0.5 2 d SPD . 1 S1B S 0.8112(3) 0.5 -0.1292(14) 0.0603(7) Uani 0.5 2 d SPD . 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 C1 0.037(4) 0.071(6) 0.045(4) 0.000(4) 0.003(3) -0.008(4) C2 0.051(7) 0.075(8) 0.032(5) 0 0.015(5) 0 C3 0.053(5) 0.070(6) 0.051(5) 0.002(4) -0.002(4) -0.011(4) C4 0.087(7) 0.073(7) 0.055(5) 0.004(5) 0.007(5) -0.012(6) C5 0.079(7) 0.072(6) 0.071(6) 0.004(5) 0.022(5) -0.024(6) C6 0.047(5) 0.064(6) 0.088(7) 0.001(5) 0.013(5) -0.009(4) C7 0.036(4) 0.043(4) 0.061(5) -0.004(4) 0.005(3) -0.002(3) C8 0.042(4) 0.048(5) 0.067(5) -0.004(4) -0.011(4) 0.000(4) C9 0.046(7) 0.131(13) 0.036(6) 0 -0.007(5) 0 C10 0.058(8) 0.077(9) 0.055(7) 0 -0.010(6) 0 C11 0.071(10) 0.067(9) 0.091(11) 0 -0.032(9) 0 C12A 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 C12B 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 F1A 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 F1B 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 F2A 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 F2B 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 N1 0.042(3) 0.053(4) 0.042(3) -0.004(3) 0.001(3) -0.001(3) N2 0.032(4) 0.045(5) 0.049(5) 0 -0.003(4) 0 O1 0.056(4) 0.083(5) 0.064(4) -0.019(4) 0.014(3) 0.005(3) O2 0.030(4) 0.112(8) 0.051(5) 0 -0.003(4) 0 O3A 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 O3B 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 O4A 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 O4B 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 Re1 0.0298(3) 0.0613(4) 0.0405(3) 0 0.00142(17) 0 S1A 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 S1B 0.0536(15) 0.0628(15) 0.0596(16) 0 -0.0020(12) 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 O1 1.135(10) . ? C2 O2 1.158(14) . ? C3 C4 1.356(13) . ? C3 H3 0.93 . ? C4 C5 1.402(14) . ? C4 H4 0.93 . ? C5 H5 0.93 . ? C6 C5 1.381(14) . ? C6 H6 0.93 . ? C7 C6 1.373(12) . ? C7 C8 1.486(11) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 C10 1.487(17) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 C11 1.145(19) . ? C11 H11 0.93 . ? C12A F1A 1.330(5) . ? C12A F2A 1.332(5) . ? C12A F2A 1.332(5) 6_565 ? C12B F1B 1.333(5) . ? C12B F1B 1.333(5) 6_565 ? C12B F2B 1.331(5) . ? N1 C3 1.346(11) . ? N1 C7 1.356(9) . ? N2 C8 1.485(10) . ? N2 C8 1.485(10) 6_575 ? N2 C9 1.510(15) . ? Re1 C1 1.942(10) . ? Re1 C1 1.942(10) 6_575 ? Re1 C2 1.909(12) . ? Re1 N1 2.171(7) . ? Re1 N1 2.171(7) 6_575 ? Re1 N2 2.223(8) . ? S1A C12A 1.820(16) . ? S1A O3A 1.428(13) . ? S1A O4A 1.400(9) . ? S1A O4A 1.400(9) 6_565 ? S1B C12B 1.796(15) . ? S1B O3B 1.429(13) . ? S1B O4B 1.400(9) . ? S1B O4B 1.400(9) 6_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Re1 C1 90.1(5) . 6_575 ? C1 Re1 N1 172.1(3) . 6_575 ? C1 Re1 N1 172.1(3) 6_575 . ? C1 Re1 N1 94.8(3) . . ? C1 Re1 N1 94.8(3) 6_575 6_575 ? C1 Re1 N2 95.8(3) . . ? C1 Re1 N2 95.8(3) 6_575 . ? C10 C11 H11 180 . . ? C10 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C10 C9 N2 113.8(11) . . ? C11 C10 C9 174.1(17) . . ? C2 Re1 C1 88.4(3) . . ? C2 Re1 C1 88.4(3) . 6_575 ? C2 Re1 N1 98.0(3) . . ? C2 Re1 N1 98.0(3) . 6_575 ? C2 Re1 N2 174.1(4) . . ? C3 C4 C5 118.8(9) . . ? C3 C4 H4 120.6 . . ? C3 N1 C7 118.7(7) . . ? C3 N1 Re1 125.3(5) . . ? C4 C3 H3 118.6 . . ? C4 C5 H5 120.8 . . ? C5 C4 H4 120.6 . . ? C5 C6 H6 120 . . ? C6 C5 C4 118.4(9) . . ? C6 C5 H5 120.8 . . ? C6 C7 C8 122.1(7) . . ? C7 C6 C5 120.0(8) . . ? C7 C6 H6 120 . . ? C7 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C7 N1 Re1 115.3(5) . . ? C8 N2 C8 109.4(9) 6_575 . ? C8 N2 C9 109.0(6) . . ? C8 N2 C9 109.0(6) 6_575 . ? C8 N2 Re1 109.1(5) . . ? C8 N2 Re1 109.1(5) 6_575 . ? C9 N2 Re1 111.2(7) . . ? F1A C12A F2A 109.4(9) . . ? F1A C12A F2A 109.4(9) . 6_565 ? F1A C12A S1A 109.1(9) . . ? F1B C12B F1B 102.6(12) . 6_565 ? F1B C12B S1B 112.3(7) . . ? F1B C12B S1B 112.3(7) 6_565 . ? F2A C12A F2A 109.4(13) . 6_565 ? F2A C12A S1A 109.7(7) . . ? F2A C12A S1A 109.7(7) 6_565 . ? F2B C12B F1B 109.2(9) . . ? F2B C12B F1B 109.2(9) . 6_565 ? F2B C12B S1B 110.9(9) . . ? H8A C8 H8B 107.9 . . ? H9A C9 H9B 107.7 . . ? N1 C3 C4 122.9(8) . . ? N1 C3 H3 118.6 . . ? N1 C7 C6 121.1(8) . . ? N1 C7 C8 116.7(7) . . ? N1 Re1 N1 79.7(3) . 6_575 ? N1 Re1 N2 77.5(2) . . ? N1 Re1 N2 77.5(2) 6_575 . ? N2 C8 C7 111.8(7) . . ? N2 C8 H8A 109.3 . . ? N2 C8 H8B 109.3 . . ? N2 C9 H9A 108.8 . . ? N2 C9 H9B 108.8 . . ? O1 C1 Re1 179.1(8) . . ? O2 C2 Re1 179.5(9) . . ? O3A S1A C12A 102.1(8) . . ? O3B S1B C12B 103.7(8) . . ? O4A S1A C12A 104.9(6) . . ? O4A S1A C12A 104.9(6) 6_565 . ? O4A S1A O3A 112.4(7) . . ? O4A S1A O3A 112.4(7) 6_565 . ? O4A S1A O4A 118.2(13) 6_565 . ? O4B S1B C12B 106.3(6) . . ? O4B S1B C12B 106.3(6) 6_565 . ? O4B S1B O3B 110.6(8) . . ? O4B S1B O3B 110.6(8) 6_565 . ? O4B S1B O4B 118.2(12) 6_565 . ? # END data_6 _database_code_depnum_ccdc_archive 'CCDC 751745' #TrackingRef 'ccdc_deposit_Benny.cif' _audit_creation_date 2009-07-22T02:25:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum ; C51.37 H44.10 Br0.74 F3.80 N12 O9.80 Re2 S1.27 ; _chemical_formula_moiety ; C25 H22 N6 O3 Re, C25 H22 N6 O3 Re, C1.37 F3.80 S1.27 O3.8, Br0.74 ; _chemical_formula_weight 1530.01 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _cell_length_a 10.2803(11) _cell_length_b 18.7456(19) _cell_length_c 30.539(4) _cell_angle_alpha 90 _cell_angle_beta 99.339(5) _cell_angle_gamma 90 _cell_volume 5807.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 210(1) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _cell_measurement_reflns_used 24577 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2978.9 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.793 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.755 _exptl_absorpt_correction_T_max 0.821 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 210(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_unetI/netI 0.0567 _diffrn_reflns_number 35711 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 10203 _reflns_number_gt 7468 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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. A CIF-check reported level-B alert and level-C alerts: Level-B alerts: 1. "Isotropic non-H Atoms in Main Residue(s) ....... 6" One of two phenyl groups (C45-C50) exhibits continuous positional disorder. Despite the extensive use of restrains, the atoms of the phenyl group exhibited unreasonable geometries and ADPs. The atoms of the phenyl group were, therefore, isotropically refined. Level-C alerts: 1. "Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio" "Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio" "Large Solvent/Anion O Ueq(max)/Ueq(min) ... 3.16 Ratio" The large Ueq(max)/Ueq(min) for C and O atoms are attributed to significant thermal motions of the CF3SO3- counterions. 2. "Check Low Ueq as Compared to Neighbors for C20" The low Ueq of C20 is attributed to the wagging motion of the corresponding phenyl group (C20-C25). 3. "Unitcell contains non-integer number of atoms .." The unit cell contains non-integer numbers of certain atom types (e.q. S, F) owing to partial occupacies of the CF3SO3- and Br- counterions. 4. "Low 'Solvent' Ueq as Compared to Neighbours of C51" "Low 'Solvent' Ueq as Compared to Neighbours of C52" "Low 'Solvent' Ueq as Compared to Neighbours of S1" The listed alerts are attributed to high Ueq parameters of O(SO3) and F(CF3) atoms exhibiting rotational motions aroung C51, C52 and S1. No significant residual electron density in the Fourier map was found to be attributed to two-fold rotational disorders of the SO3 and CF3 groups. ; _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^)+(0.0819P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 10203 _refine_ls_number_parameters 738 _refine_ls_number_restraints 101 _refine_ls_R_factor_all 0.076 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1375 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.036 _refine_diff_density_min -1.606 _refine_diff_density_rms 0.193 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Br1 Br 0.3056(4) 0.09215(15) 0.61318(15) 0.0938(15) Uani 0.554(5) 1 d P C 6 Br2 Br 0.1630(12) 0.7267(7) 0.2464(4) 0.051(3) Uani 0.181(6) 1 d PU B 4 C1 C 0.9602(9) 0.5727(5) 0.5342(3) 0.039(2) Uani 1 1 d . . . C2 C 1.1199(9) 0.6461(5) 0.5912(3) 0.040(2) Uani 1 1 d . . . C3 C 1.1886(9) 0.6283(4) 0.5116(3) 0.036(2) Uani 1 1 d . . . C4 C 1.1715(9) 0.8112(5) 0.5649(3) 0.049(2) Uani 1 1 d . . . C5 C 1.1976(11) 0.8837(5) 0.5648(3) 0.064(3) Uani 1 1 d . . . C6 C 1.1355(11) 0.9210(5) 0.5287(4) 0.070(3) Uani 1 1 d . . . C7 C 1.0652(10) 0.8865(5) 0.4926(3) 0.057(3) Uani 1 1 d . . . C8 C 1.0466(9) 0.8141(4) 0.4941(3) 0.041(2) Uani 1 1 d . . . C9 C 0.9759(8) 0.7731(4) 0.4568(3) 0.036(2) Uani 1 1 d . . . C10 C 0.7836(8) 0.7038(5) 0.4708(3) 0.043(2) Uani 1 1 d . . . C11 C 0.7670(8) 0.7364(4) 0.5153(3) 0.042(2) Uani 1 1 d . . . C12 C 0.6575(10) 0.7755(5) 0.5202(4) 0.059(3) Uani 1 1 d . . . C13 C 0.6480(12) 0.8006(6) 0.5634(4) 0.066(3) Uani 1 1 d . . . C14 C 0.7460(12) 0.7870(6) 0.5972(4) 0.068(3) Uani 1 1 d . . . C15 C 0.8515(10) 0.7468(5) 0.5901(3) 0.054(3) Uani 1 1 d . . . C16 C 0.9452(8) 0.6501(4) 0.4302(3) 0.0351(19) Uani 1 1 d . . . C17 C 0.8683(8) 0.6693(4) 0.3867(3) 0.035(2) Uani 1 1 d . . . C18 C 0.9048(9) 0.7046(5) 0.3508(3) 0.046(2) Uani 1 1 d . . . C19 C 0.7759(11) 0.7446(6) 0.2771(3) 0.066(3) Uani 1 1 d . . . C20 C 0.7169(11) 0.6960(5) 0.2398(3) 0.053(3) Uani 1 1 d . . . C21 C 0.7881(14) 0.6397(8) 0.2293(5) 0.087(4) Uani 1 1 d . . . C22 C 0.7351(18) 0.5930(7) 0.1942(5) 0.101(5) Uani 1 1 d . . . C23 C 0.6121(18) 0.6057(8) 0.1702(4) 0.089(5) Uani 1 1 d . . . C24 C 0.5436(15) 0.6603(9) 0.1804(4) 0.094(5) Uani 1 1 d . . . C25 C 0.5922(11) 0.7068(7) 0.2163(4) 0.072(3) Uani 1 1 d . . . C26 C 0.5804(8) 0.5549(4) 0.5495(3) 0.036(2) Uani 1 1 d . . . C27 C 0.4659(8) 0.6428(5) 0.5986(3) 0.040(2) Uani 1 1 d . . . C28 C 0.3573(9) 0.5134(4) 0.5808(3) 0.0337(19) Uani 1 1 d . . . C29 C 0.4430(9) 0.5869(5) 0.6980(3) 0.046(2) Uani 1 1 d . . . C30 C 0.4420(11) 0.5834(5) 0.7419(3) 0.058(3) Uani 1 1 d . . . C31 C 0.4903(12) 0.5221(6) 0.7644(3) 0.066(3) Uani 1 1 d . . . C32 C 0.5383(10) 0.4684(5) 0.7404(3) 0.055(3) Uani 1 1 d . . . C33 C 0.5383(8) 0.4755(4) 0.6960(3) 0.0355(19) Uani 1 1 d . . . C34 C 0.5822(8) 0.4172(4) 0.6692(2) 0.037(2) Uani 1 1 d . . . C35 C 0.7592(8) 0.4473(4) 0.6272(3) 0.036(2) Uani 1 1 d . . . C36 C 0.8067(8) 0.5126(4) 0.6515(3) 0.037(2) Uani 1 1 d . . . C37 C 0.9269(9) 0.5189(5) 0.6792(3) 0.054(3) Uani 1 1 d . . . C38 C 0.9637(10) 0.5828(6) 0.6987(3) 0.062(3) Uani 1 1 d . . . C39 C 0.8831(10) 0.6398(5) 0.6920(3) 0.055(3) Uani 1 1 d . . . C40 C 0.7617(8) 0.6315(5) 0.6648(3) 0.040(2) Uani 1 1 d . . . C41 C 0.5646(7) 0.3826(4) 0.5906(3) 0.0334(19) Uani 1 1 d . A . C42 C 0.6256(8) 0.3106(4) 0.6008(3) 0.038(2) Uani 1 1 d . . . C43 C 0.5824(9) 0.2527(5) 0.6206(3) 0.045(2) Uani 1 1 d . A . C44A C 0.6857(11) 0.1298(6) 0.6425(4) 0.077(3) Uani 0.632(11) 1 d PD A 1 C44B C 0.6857(11) 0.1298(6) 0.6425(4) 0.077(3) Uani 0.368(11) 1 d PD A 2 C45A C 0.7174(11) 0.0764(5) 0.6119(3) 0.087 Uiso 0.632(11) 1 d PGD A 1 C45B C 0.7093(14) 0.0894(5) 0.6052(3) 0.087 Uiso 0.368(11) 1 d PGD A 2 C46A C 0.6256(10) 0.0580(7) 0.5750(4) 0.089 Uiso 0.632(11) 1 d PGD A 1 C46B C 0.6274(12) 0.1053(5) 0.5655(3) 0.089 Uiso 0.368(11) 1 d PGD A 2 C47A C 0.6533(12) 0.0036(7) 0.5470(4) 0.089 Uiso 0.632(11) 1 d PG A 1 C47B C 0.6189(11) 0.0586(8) 0.5298(4) 0.089 Uiso 0.368(11) 1 d PGD A 2 C48A C 0.7728(14) -0.0324(6) 0.5559(4) 0.097 Uiso 0.632(11) 1 d PGD A 1 C48B C 0.6923(14) -0.0040(8) 0.5337(5) 0.097 Uiso 0.368(11) 1 d PGD A 2 C49A C 0.8647(11) -0.0140(7) 0.5927(4) 0.098 Uiso 0.632(11) 1 d PG A 1 C49B C 0.7742(14) -0.0200(5) 0.5734(6) 0.098 Uiso 0.368(11) 1 d PG A 2 C50A C 0.8370(10) 0.0404(6) 0.6207(3) 0.097 Uiso 0.695(12) 1 d PGD A 1 C50B C 0.7826(14) 0.0267(6) 0.6091(4) 0.097 Uiso 0.405(12) 1 d PGD A 2 C51 C 0.1626(10) 0.6985(6) 0.2057(4) 0.071(5) Uani 0.819(6) 1 d PD B 3 C52 C 0.1683(15) 0.0678(8) 0.6575(5) 0.094(10) Uiso 0.446(5) 1 d PD C 5 F1 F 0.2187(11) 0.7395(6) 0.1798(3) 0.127(4) Uani 0.819(6) 1 d PD B 3 F2 F 0.2165(8) 0.6357(5) 0.2002(3) 0.090(3) Uani 0.819(6) 1 d PD B 3 F3 F 0.0382(8) 0.6953(5) 0.1878(2) 0.096(3) Uani 0.819(6) 1 d PD B 3 F4 F 0.1101(18) 0.0053(7) 0.6512(8) 0.159(11) Uani 0.446(5) 1 d PD C 5 F5 F 0.0784(13) 0.1217(7) 0.6512(5) 0.097(5) Uani 0.446(5) 1 d PDU C 5 F6 F 0.2213(17) 0.0725(10) 0.6984(5) 0.116(7) Uani 0.446(5) 1 d PD C 5 H4 H 1.2056 0.7845 0.5902 0.059 Uiso 1 1 calc R . . H5 H 1.2543 0.906 0.588 0.077 Uiso 1 1 calc R . . H6 H 1.1411 0.9711 0.5287 0.084 Uiso 1 1 calc R . . H7 H 1.0302 0.9125 0.467 0.069 Uiso 1 1 calc R . . H9A H 1.0342 0.7676 0.4347 0.043 Uiso 1 1 calc R . . H9B H 0.8999 0.8014 0.4431 0.043 Uiso 1 1 calc R . . H10A H 0.7473 0.6554 0.4686 0.051 Uiso 1 1 calc R . . H10B H 0.7353 0.7323 0.4466 0.051 Uiso 1 1 calc R . . H12 H 0.5912 0.7851 0.496 0.07 Uiso 1 1 calc R . . H13 H 0.5736 0.8267 0.5683 0.079 Uiso 1 1 calc R . . H14 H 0.742 0.8052 0.6256 0.082 Uiso 1 1 calc R . . H15 H 0.9185 0.737 0.6142 0.065 Uiso 1 1 calc R . . H16A H 1.0388 0.648 0.4275 0.042 Uiso 1 1 calc R . . H16B H 0.9186 0.6024 0.4385 0.042 Uiso 1 1 calc R . . H18 H 0.989 0.7221 0.3483 0.055 Uiso 1 1 calc R . . H19A H 0.8615 0.762 0.2713 0.079 Uiso 1 1 calc R . . H19B H 0.7182 0.786 0.278 0.079 Uiso 1 1 calc R . . H21 H 0.8729 0.6314 0.2452 0.104 Uiso 1 1 calc R . . H22 H 0.7842 0.5534 0.1874 0.122 Uiso 1 1 calc R . . H23 H 0.5776 0.5753 0.1467 0.107 Uiso 1 1 calc R . . H24 H 0.46 0.6691 0.1637 0.113 Uiso 1 1 calc R . . H25 H 0.5397 0.7445 0.2238 0.086 Uiso 1 1 calc R . . H29 H 0.4067 0.6276 0.6827 0.055 Uiso 1 1 calc R . . H30 H 0.4095 0.6215 0.757 0.069 Uiso 1 1 calc R . . H31 H 0.4904 0.5173 0.795 0.079 Uiso 1 1 calc R . . H32 H 0.5715 0.4264 0.755 0.066 Uiso 1 1 calc R . . H34A H 0.5126 0.381 0.6644 0.044 Uiso 1 1 calc R . . H34B H 0.6602 0.3948 0.6866 0.044 Uiso 1 1 calc R . . H35A H 0.8045 0.4058 0.6422 0.043 Uiso 1 1 calc R . . H35B H 0.7805 0.4495 0.5971 0.043 Uiso 1 1 calc R . . H37 H 0.9831 0.4792 0.6845 0.065 Uiso 1 1 calc R . . H38 H 1.0461 0.5872 0.7171 0.075 Uiso 1 1 calc R . . H39 H 0.9081 0.6839 0.7053 0.066 Uiso 1 1 calc R . . H40 H 0.7036 0.6705 0.6608 0.048 Uiso 1 1 calc R . . H41A H 0.4688 0.3786 0.5887 0.04 Uiso 1 1 calc R . . H41B H 0.5824 0.3983 0.5615 0.04 Uiso 1 1 calc R . . H43 H 0.5024 0.2481 0.6316 0.055 Uiso 1 1 calc R . . H44A H 0.7535 0.1298 0.6691 0.093 Uiso 0.632(11) 1 calc PR A 1 H44B H 0.6011 0.1181 0.6517 0.093 Uiso 0.632(11) 1 calc PR A 1 H44C H 0.7588 0.1261 0.6674 0.093 Uiso 0.368(11) 1 calc PR A 2 H44D H 0.6031 0.1161 0.6524 0.093 Uiso 0.368(11) 1 calc PR A 2 H46A H 0.5447 0.0824 0.5691 0.107 Uiso 0.632(11) 1 calc PR A 1 H46B H 0.5778 0.1476 0.5629 0.107 Uiso 0.368(11) 1 calc PR A 2 H47A H 0.5912 -0.0088 0.5221 0.106 Uiso 0.632(11) 1 calc PR A 1 H47B H 0.5635 0.0693 0.503 0.106 Uiso 0.368(11) 1 calc PR A 2 H48A H 0.7916 -0.0692 0.5369 0.117 Uiso 0.632(11) 1 calc PR A 1 H48B H 0.6866 -0.0356 0.5096 0.117 Uiso 0.368(11) 1 calc PR A 2 H49A H 0.9456 -0.0384 0.5987 0.117 Uiso 0.632(11) 1 calc PR A 1 H49B H 0.8238 -0.0623 0.576 0.117 Uiso 0.368(11) 1 calc PR A 2 H50A H 0.8991 0.0528 0.6456 0.116 Uiso 0.695(12) 1 calc PR A 1 H50B H 0.838 0.016 0.6359 0.116 Uiso 0.405(12) 1 calc PRD A 2 N1 N 1.0999(7) 0.7772(3) 0.5305(2) 0.0380(17) Uani 1 1 d . . . N10 N 0.7471(7) 0.2929(4) 0.5902(3) 0.0471(19) Uani 1 1 d . A . N11 N 0.7765(8) 0.2267(4) 0.6025(3) 0.051(2) Uani 1 1 d . A . N12 N 0.6776(8) 0.2031(4) 0.6215(3) 0.050(2) Uani 1 1 d . . . N2 N 0.9281(6) 0.7017(3) 0.4669(2) 0.0307(15) Uani 1 1 d . . . N3 N 0.8632(7) 0.7204(3) 0.5494(2) 0.0422(18) Uani 1 1 d . . . N4 N 0.7368(7) 0.6529(4) 0.3747(2) 0.0462(19) Uani 1 1 d . . . N5 N 0.6943(8) 0.6772(4) 0.3345(3) 0.053(2) Uani 1 1 d . . . N6 N 0.7938(8) 0.7087(4) 0.3199(2) 0.052(2) Uani 1 1 d . . . N7 N 0.4923(6) 0.5359(3) 0.6748(2) 0.0328(16) Uani 1 1 d . . . N8 N 0.6154(6) 0.4386(3) 0.6248(2) 0.0274(14) Uani 1 1 d . . . N9 N 0.7247(6) 0.5701(4) 0.6442(2) 0.0354(16) Uani 1 1 d . . . O1 O 0.9166(6) 0.5175(3) 0.5380(2) 0.0510(16) Uani 1 1 d . . . O2 O 1.1695(7) 0.6314(4) 0.6271(2) 0.0594(18) Uani 1 1 d . . . O3 O 1.2795(6) 0.6082(3) 0.4990(2) 0.0472(15) Uani 1 1 d . . . O4 O 0.6073(6) 0.5630(3) 0.5145(2) 0.0512(16) Uani 1 1 d . . . O5 O 0.4294(6) 0.6999(3) 0.5945(2) 0.0533(17) Uani 1 1 d . . . O6 O 0.2544(6) 0.4925(3) 0.5656(2) 0.0463(15) Uani 1 1 d . . . O7 O 0.3271(7) 0.7359(4) 0.2715(3) 0.071(3) Uani 0.819(6) 1 d PD B 3 O8 O 0.1351(7) 0.6678(4) 0.2842(3) 0.070(3) Uani 0.819(6) 1 d PD B 3 O9 O 0.1084(10) 0.7913(5) 0.2606(3) 0.098(4) Uani 0.819(6) 1 d PD B 3 O10 O 0.2018(15) 0.0776(8) 0.5780(4) 0.081(6) Uani 0.446(5) 1 d PD C 5 O11 O 0.3754(10) 0.0209(6) 0.6280(4) 0.038(3) Uiso 0.446(5) 1 d PD C 5 O12 O 0.3407(13) 0.1485(6) 0.6358(7) 0.121(10) Uani 0.446(5) 1 d PD C 5 Re1 Re 1.03548(3) 0.666693(17) 0.532717(11) 0.03326(12) Uani 1 1 d . . . Re2 Re 0.52982(3) 0.546457(16) 0.607017(10) 0.02990(12) Uani 1 1 d . . . S1 S 0.1865(7) 0.7276(4) 0.26196(19) 0.0498(15) Uani 0.819(6) 1 d PD B 3 S2 S 0.2835(11) 0.0827(6) 0.6221(4) 0.076(4) Uiso 0.446(5) 1 d PD C 5 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 Br1 0.087(2) 0.0369(14) 0.127(3) 0.0176(15) -0.073(2) -0.0002(13) Br2 0.040(4) 0.059(4) 0.048(8) 0.031(5) -0.008(5) 0.014(3) C1 0.039(5) 0.041(5) 0.038(5) 0.002(4) 0.008(4) 0.007(4) C2 0.042(5) 0.042(5) 0.038(6) 0.005(4) 0.012(4) 0.003(4) C3 0.047(5) 0.039(5) 0.023(4) 0.011(4) 0.008(4) 0.006(4) C4 0.063(6) 0.038(5) 0.045(6) -0.009(4) 0.002(5) -0.008(5) C5 0.080(8) 0.051(6) 0.056(7) -0.013(5) -0.009(6) -0.003(6) C6 0.098(9) 0.035(6) 0.074(8) -0.010(5) 0.007(7) -0.001(6) C7 0.074(7) 0.033(5) 0.057(7) 0.002(5) -0.012(5) -0.003(5) C8 0.045(5) 0.029(4) 0.050(6) 0.010(4) 0.016(4) 0.006(4) C9 0.031(4) 0.030(4) 0.042(5) -0.008(4) -0.005(4) 0.008(4) C10 0.040(5) 0.049(5) 0.042(5) 0.013(4) 0.016(4) 0.010(4) C11 0.041(5) 0.030(4) 0.056(6) 0.005(4) 0.015(5) 0.012(4) C12 0.055(6) 0.050(6) 0.075(8) 0.016(5) 0.024(6) 0.015(5) C13 0.079(8) 0.049(6) 0.082(9) 0.005(6) 0.048(7) 0.009(6) C14 0.088(9) 0.057(7) 0.067(8) -0.001(6) 0.037(7) 0.025(6) C15 0.074(7) 0.047(6) 0.048(6) 0.001(5) 0.028(5) 0.011(5) C16 0.036(5) 0.029(4) 0.041(5) -0.005(4) 0.008(4) -0.001(4) C17 0.036(5) 0.027(4) 0.044(5) 0.002(4) 0.012(4) 0.002(4) C18 0.044(5) 0.054(6) 0.039(5) 0.000(4) 0.005(4) -0.009(5) C19 0.080(8) 0.067(7) 0.043(6) 0.012(5) -0.009(5) -0.020(6) C20 0.073(7) 0.049(6) 0.040(6) 0.009(5) 0.017(5) -0.012(6) C21 0.083(9) 0.093(10) 0.082(10) 0.031(8) 0.006(7) -0.012(8) C22 0.163(16) 0.082(10) 0.070(10) -0.006(8) 0.052(10) -0.026(11) C23 0.136(14) 0.088(10) 0.043(8) 0.002(7) 0.014(9) -0.052(10) C24 0.082(10) 0.140(14) 0.054(9) 0.038(9) -0.006(7) -0.047(10) C25 0.060(7) 0.097(9) 0.058(7) 0.030(7) 0.010(6) -0.005(7) C26 0.042(5) 0.028(4) 0.035(5) 0.001(4) 0.000(4) -0.006(4) C27 0.038(5) 0.044(5) 0.038(5) 0.002(4) 0.012(4) -0.002(4) C28 0.043(5) 0.027(4) 0.033(5) 0.007(4) 0.014(4) 0.002(4) C29 0.058(6) 0.042(5) 0.038(6) -0.001(4) 0.009(4) 0.009(5) C30 0.085(8) 0.047(6) 0.047(6) -0.011(5) 0.028(5) -0.002(5) C31 0.113(10) 0.056(6) 0.035(6) -0.005(5) 0.031(6) -0.013(6) C32 0.075(7) 0.047(6) 0.044(6) 0.009(5) 0.013(5) 0.004(5) C33 0.035(5) 0.041(5) 0.031(5) 0.002(4) 0.008(4) -0.003(4) C34 0.042(5) 0.047(5) 0.021(4) 0.010(4) 0.005(4) 0.001(4) C35 0.034(5) 0.032(4) 0.042(5) 0.010(4) 0.006(4) -0.001(4) C36 0.036(5) 0.037(5) 0.037(5) 0.008(4) 0.004(4) -0.009(4) C37 0.043(6) 0.059(6) 0.057(6) 0.013(5) -0.005(5) -0.010(5) C38 0.050(6) 0.079(8) 0.051(7) -0.004(6) -0.013(5) -0.022(6) C39 0.066(7) 0.047(6) 0.053(6) -0.009(5) 0.011(5) -0.022(5) C40 0.040(5) 0.036(5) 0.042(5) -0.010(4) 0.001(4) -0.010(4) C41 0.025(4) 0.036(4) 0.038(5) -0.004(4) 0.001(4) -0.002(4) C42 0.038(5) 0.035(5) 0.041(5) 0.001(4) 0.011(4) -0.002(4) C43 0.047(5) 0.038(5) 0.054(6) 0.001(4) 0.016(5) 0.002(4) C44A 0.087 0.047(6) 0.104(10) 0.018(6) 0.032(7) 0.009(6) C44B 0.087 0.047(6) 0.104(10) 0.018(6) 0.032(7) 0.009(6) C51 0.044(8) 0.077(10) 0.091(13) 0.051(10) 0.008(8) 0.007(7) F1 0.156(10) 0.159(10) 0.070(6) 0.038(7) 0.027(6) -0.013(8) F2 0.084(6) 0.102(7) 0.081(6) -0.007(5) 0.000(5) 0.029(5) F3 0.091(7) 0.139(8) 0.052(5) 0.005(5) -0.009(4) 0.038(6) F4 0.158(18) 0.046(10) 0.30(3) 0.051(14) 0.13(2) 0.024(11) F5 0.094(8) 0.064(7) 0.126(9) -0.005(7) -0.004(7) 0.045(7) F6 0.112(14) 0.120(15) 0.124(16) 0.027(12) 0.043(12) 0.060(12) N1 0.046(4) 0.032(4) 0.036(4) -0.004(3) 0.006(3) 0.005(3) N2 0.031(4) 0.028(4) 0.034(4) 0.006(3) 0.009(3) 0.003(3) N3 0.056(5) 0.029(4) 0.049(5) 0.002(3) 0.028(4) 0.004(3) N4 0.042(4) 0.053(5) 0.041(5) 0.006(4) 0.000(4) -0.012(4) N5 0.044(5) 0.058(5) 0.052(5) 0.012(4) -0.003(4) -0.009(4) N6 0.057(5) 0.063(5) 0.034(4) 0.009(4) 0.003(4) -0.025(4) N7 0.034(4) 0.036(4) 0.028(4) -0.002(3) 0.004(3) -0.002(3) N8 0.028(3) 0.027(3) 0.027(4) 0.005(3) 0.003(3) 0.000(3) N9 0.035(4) 0.038(4) 0.034(4) 0.002(3) 0.005(3) -0.009(3) N10 0.044(5) 0.047(5) 0.053(5) 0.004(4) 0.016(4) 0.001(4) N11 0.050(5) 0.043(5) 0.063(5) 0.003(4) 0.020(4) 0.003(4) N12 0.066(5) 0.028(4) 0.059(5) 0.009(4) 0.021(4) 0.010(4) O1 0.057(4) 0.040(4) 0.054(4) 0.004(3) 0.005(3) -0.005(3) O2 0.070(5) 0.067(5) 0.040(4) 0.012(3) 0.005(4) 0.008(4) O3 0.045(4) 0.058(4) 0.042(4) 0.007(3) 0.017(3) 0.011(3) O4 0.058(4) 0.059(4) 0.039(4) 0.007(3) 0.013(3) -0.004(3) O5 0.053(4) 0.027(3) 0.078(5) 0.002(3) 0.006(3) 0.007(3) O6 0.037(4) 0.045(4) 0.054(4) 0.008(3) -0.001(3) -0.007(3) O7 0.054(6) 0.079(6) 0.080(7) 0.027(5) 0.007(5) 0.007(5) O8 0.047(5) 0.101(7) 0.057(6) 0.034(5) -0.003(4) 0.003(5) O9 0.116(9) 0.096(8) 0.069(7) 0.004(6) -0.022(6) 0.069(7) O10 0.102(14) 0.053(10) 0.077(12) -0.020(9) -0.019(10) 0.044(10) O12 0.046(10) 0.037(9) 0.29(3) -0.051(14) 0.063(14) -0.007(8) Re1 0.0392(2) 0.0308(2) 0.0306(2) 0.00158(14) 0.00799(15) 0.00356(14) Re2 0.0343(2) 0.02874(19) 0.0258(2) 0.00220(13) 0.00247(14) -0.00112(14) S1 0.052(3) 0.061(3) 0.032(3) 0.020(3) -0.005(2) 0.020(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 O1 1.141(10) . ? C2 O2 1.165(10) . ? C3 O3 1.132(9) . ? C4 C5 1.386(13) . ? C4 H4 0.94 . ? C4 N1 1.342(11) . ? C5 C6 1.371(14) . ? C5 H5 0.94 . ? C6 H6 0.94 . ? C7 C6 1.379(14) . ? C7 C8 1.373(11) . ? C7 H7 0.94 . ? C9 C8 1.465(12) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 N2 1.475(10) . ? C10 C11 1.523(12) . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 N2 1.511(10) . ? C11 C12 1.372(12) . ? C12 H12 0.94 . ? C13 C12 1.417(15) . ? C13 H13 0.94 . ? C14 C13 1.345(16) . ? C14 C15 1.367(13) . ? C14 H14 0.94 . ? C15 H15 0.94 . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 N2 1.512(10) . ? C17 C16 1.477(11) . ? C18 C17 1.384(12) . ? C18 H18 0.94 . ? C18 N6 1.360(11) . ? C19 C20 1.508(13) . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C20 C21 1.352(17) . ? C21 C22 1.422(17) . ? C21 H21 0.94 . ? C22 C23 1.37(2) . ? C22 H22 0.94 . ? C23 H23 0.94 . ? C24 C23 1.310(19) . ? C24 H24 0.94 . ? C25 C20 1.379(15) . ? C25 C24 1.425(18) . ? C25 H25 0.94 . ? C26 O4 1.157(10) . ? C27 O5 1.135(10) . ? C28 O6 1.153(9) . ? C29 C30 1.343(12) . ? C29 H29 0.94 . ? C29 N7 1.337(10) . ? C30 C31 1.389(14) . ? C30 H30 0.94 . ? C31 H31 0.94 . ? C32 C31 1.381(13) . ? C32 C33 1.363(12) . ? C32 H32 0.94 . ? C34 C33 1.479(11) . ? C34 H34A 0.98 . ? C34 H34B 0.98 . ? C34 N8 1.507(9) . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C36 C35 1.473(11) . ? C36 N9 1.365(10) . ? C37 C36 1.384(11) . ? C37 C38 1.366(14) . ? C37 H37 0.94 . ? C38 C39 1.346(14) . ? C38 H38 0.94 . ? C39 H39 0.94 . ? C40 C39 1.391(12) . ? C40 H40 0.94 . ? C40 N9 1.336(10) . ? C41 C42 1.500(11) . ? C41 H41A 0.98 . ? C41 H41B 0.98 . ? C42 C43 1.352(11) . ? C42 N10 1.380(10) . ? C43 H43 0.94 . ? C44A C45A 1.443(14) . ? C44A H44A 0.98 . ? C44A H44B 0.98 . ? C44A N12 1.513(12) . ? C45A C46A 1.39 . ? C45A C50A 1.39 . ? C45B C46B 1.39 . ? C45B C50B 1.39 . ? C46A C47A 1.39 . ? C46A H46A 0.94 . ? C46B C47B 1.39 . ? C46B H46B 0.94 . ? C47A C48A 1.39 . ? C47A H47A 0.94 . ? C47B C48B 1.39 . ? C47B H47B 0.94 . ? C48A C49A 1.39 . ? C48A H48A 0.94 . ? C48B C49B 1.39 . ? C48B H48B 0.94 . ? C49A C50A 1.39 . ? C49A H49A 0.94 . ? C49B C50B 1.39 . ? C49B H49B 0.94 . ? C50A H50A 0.94 . ? C50B H50B 0.94 . ? C51 F1 1.301(11) . ? C51 F2 1.323(11) . ? C51 F3 1.308(10) . ? C52 F4 1.315(14) . ? C52 F5 1.363(13) . ? C52 F6 1.283(14) . ? N1 C8 1.347(10) . ? N11 N10 1.318(10) . ? N12 C43 1.348(11) . ? N12 N11 1.327(10) . ? N3 C11 1.350(11) . ? N3 C15 1.359(11) . ? N4 C17 1.376(10) . ? N4 N5 1.318(10) . ? N6 C19 1.455(11) . ? N6 N5 1.320(10) . ? N7 C33 1.352(10) . ? N8 C35 1.477(10) . ? N8 C41 1.512(9) . ? Re1 C1 1.928(10) . ? Re1 C2 1.894(9) . ? Re1 C3 1.934(9) . ? Re1 N1 2.179(7) . ? Re1 N2 2.230(6) . ? Re1 N3 2.169(7) . ? Re2 C26 1.917(9) . ? Re2 C27 1.925(9) . ? Re2 C28 1.926(9) . ? Re2 N7 2.175(6) . ? Re2 N8 2.237(6) . ? Re2 N9 2.182(6) . ? S1 C51 1.783(13) . ? S1 O7 1.435(9) . ? S1 O8 1.454(9) . ? S1 O9 1.434(9) . ? S2 C52 1.751(15) . ? S2 O10 1.469(12) . ? S2 O11 1.487(11) . ? S2 O12 1.402(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Re1 C3 91.1(4) . . ? C1 Re1 N1 174.1(3) . . ? C1 Re1 N2 98.5(3) . . ? C1 Re1 N3 94.1(3) . . ? C2 Re1 C1 85.2(4) . . ? C2 Re1 C3 88.0(3) . . ? C2 Re1 N1 97.4(3) . . ? C2 Re1 N2 173.8(3) . . ? C2 Re1 N3 98.0(3) . . ? C3 Re1 N1 94.3(3) . . ? C3 Re1 N2 96.9(3) . . ? C3 Re1 N3 172.3(3) . . ? C4 C5 H5 122 . . ? C4 N1 C8 120.0(8) . . ? C4 N1 Re1 123.9(6) . . ? C5 C4 H4 118.5 . . ? C5 C6 C7 121.3(9) . . ? C5 C6 H6 119.4 . . ? C6 C5 C4 115.9(9) . . ? C6 C5 H5 122 . . ? C6 C7 H7 120.2 . . ? C7 C6 H6 119.4 . . ? C7 C8 C9 123.1(8) . . ? C8 C7 C6 119.6(9) . . ? C8 C7 H7 120.2 . . ? C8 C9 H9A 108 . . ? C8 C9 H9B 108 . . ? C8 C9 N2 117.0(7) . . ? C8 N1 Re1 115.5(6) . . ? C9 N2 C10 111.0(6) . . ? C9 N2 C16 110.1(6) . . ? C9 N2 Re1 108.8(5) . . ? C10 N2 C16 108.1(6) . . ? C10 N2 Re1 106.5(5) . . ? C11 C10 H10A 109.7 . . ? C11 C10 H10B 109.7 . . ? C11 C12 C13 117.5(10) . . ? C11 C12 H12 121.2 . . ? C11 N3 C15 117.5(8) . . ? C11 N3 Re1 116.5(6) . . ? C12 C11 C10 121.7(9) . . ? C12 C13 H13 120.2 . . ? C13 C12 H12 121.2 . . ? C13 C14 C15 119.8(11) . . ? C13 C14 H14 120.1 . . ? C14 C13 C12 119.6(10) . . ? C14 C13 H13 120.2 . . ? C14 C15 H15 118.8 . . ? C15 C14 H14 120.1 . . ? C15 N3 Re1 125.5(7) . . ? C16 N2 Re1 112.3(5) . . ? C17 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? C17 C16 N2 113.6(6) . . ? C17 C18 H18 127.1 . . ? C18 C17 C16 130.9(8) . . ? C18 N6 C19 128.3(8) . . ? C20 C19 H19A 109.2 . . ? C20 C19 H19B 109.2 . . ? C20 C21 C22 120.2(13) . . ? C20 C21 H21 119.9 . . ? C20 C25 C24 119.4(13) . . ? C20 C25 H25 120.3 . . ? C21 C20 C19 118.9(11) . . ? C21 C20 C25 119.0(11) . . ? C21 C22 H22 119.9 . . ? C22 C21 H21 119.9 . . ? C22 C23 H23 120.3 . . ? C23 C22 C21 120.2(14) . . ? C23 C22 H22 119.9 . . ? C23 C24 C25 121.8(14) . . ? C23 C24 H24 119.1 . . ? C24 C23 C22 119.4(14) . . ? C24 C23 H23 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C20 C19 122.1(11) . . ? C25 C24 H24 119.1 . . ? C26 Re2 C27 86.4(3) . . ? C26 Re2 C28 90.8(3) . . ? C26 Re2 N7 174.5(3) . . ? C26 Re2 N8 98.2(3) . . ? C26 Re2 N9 95.6(3) . . ? C27 Re2 C28 88.5(3) . . ? C27 Re2 N7 95.9(3) . . ? C27 Re2 N8 173.2(3) . . ? C27 Re2 N9 98.2(3) . . ? C28 Re2 N7 94.2(3) . . ? C28 Re2 N8 96.3(3) . . ? C28 Re2 N9 170.9(3) . . ? C29 C30 C31 118.2(9) . . ? C29 C30 H30 120.9 . . ? C29 N7 C33 118.6(7) . . ? C29 N7 Re2 125.5(6) . . ? C30 C29 H29 118 . . ? C30 C31 H31 120.9 . . ? C31 C30 H30 120.9 . . ? C31 C32 H32 119.6 . . ? C32 C31 C30 118.1(9) . . ? C32 C31 H31 120.9 . . ? C32 C33 C34 121.8(8) . . ? C33 C32 C31 120.9(9) . . ? C33 C32 H32 119.6 . . ? C33 C34 H34A 108.3 . . ? C33 C34 H34B 108.3 . . ? C33 C34 N8 115.8(7) . . ? C33 N7 Re2 115.5(5) . . ? C34 N8 C41 109.5(6) . . ? C34 N8 Re2 108.7(5) . . ? C35 N8 C34 110.8(6) . . ? C35 N8 C41 110.1(6) . . ? C35 N8 Re2 105.2(4) . . ? C36 C35 H35A 109.3 . . ? C36 C35 H35B 109.3 . . ? C36 C35 N8 111.4(7) . . ? C36 C37 H37 120.1 . . ? C36 N9 Re2 114.5(5) . . ? C37 C36 C35 124.6(8) . . ? C37 C38 H38 119.7 . . ? C38 C37 C36 119.9(10) . . ? C38 C37 H37 120.1 . . ? C38 C39 C40 118.2(9) . . ? C38 C39 H39 120.9 . . ? C39 C38 C37 120.6(9) . . ? C39 C38 H38 119.7 . . ? C39 C40 H40 118.7 . . ? C40 C39 H39 120.9 . . ? C40 N9 C36 118.8(7) . . ? C40 N9 Re2 126.0(6) . . ? C41 N8 Re2 112.4(4) . . ? C42 C41 H41A 108.9 . . ? C42 C41 H41B 108.9 . . ? C42 C41 N8 113.2(6) . . ? C42 C43 H43 127.1 . . ? C43 C42 C41 131.2(8) . . ? C43 C42 N10 106.7(7) . . ? C43 N12 C44A 128.7(8) . . ? C45A C44A H44A 109.5 . . ? C45A C44A H44B 109.5 . . ? C45A C44A N12 110.9(9) . . ? C45A C46A H46A 120 . . ? C45A C50A H50A 120 . . ? C45B C46B C47B 120 . . ? C45B C46B H46B 120 . . ? C45B C50B H50B 120 . . ? C46A C45A C44A 120.1(7) . . ? C46A C45A C50A 120 . . ? C46A C47A C48A 120 . . ? C46A C47A H47A 120 . . ? C46B C45B C50B 120 . . ? C46B C47B H47B 120 . . ? C47A C46A C45A 120 . . ? C47A C46A H46A 120 . . ? C47A C48A H48A 120 . . ? C47B C46B H46B 120 . . ? C47B C48B H48B 120 . . ? C48A C47A H47A 120 . . ? C48A C49A H49A 120 . . ? C48B C47B C46B 120 . . ? C48B C47B H47B 120 . . ? C48B C49B C50B 120 . . ? C48B C49B H49B 120 . . ? C49A C48A C47A 120 . . ? C49A C48A H48A 120 . . ? C49A C50A C45A 120 . . ? C49A C50A H50A 120 . . ? C49B C48B C47B 120 . . ? C49B C48B H48B 120 . . ? C49B C50B C45B 120 . . ? C49B C50B H50B 120 . . ? C50A C45A C44A 119.8(6) . . ? C50A C49A C48A 120 . . ? C50A C49A H49A 120 . . ? C50B C49B H49B 120 . . ? F1 C51 F2 102.4(10) . . ? F1 C51 F3 106.0(10) . . ? F1 C51 S1 113.5(9) . . ? F2 C51 S1 113.5(8) . . ? F3 C51 F2 107.9(10) . . ? F3 C51 S1 112.8(8) . . ? F4 C52 F5 110.9(15) . . ? F4 C52 S2 112.9(11) . . ? F5 C52 S2 107.8(11) . . ? F6 C52 F4 108.3(19) . . ? F6 C52 F5 105.0(15) . . ? F6 C52 S2 111.6(11) . . ? H10A C10 H10B 108.2 . . ? H16A C16 H16B 107.7 . . ? H19A C19 H19B 107.9 . . ? H34A C34 H34B 107.4 . . ? H35A C35 H35B 108 . . ? H41A C41 H41B 107.7 . . ? H44A C44A H44B 108 . . ? H9A C9 H9B 107.3 . . ? N1 C4 C5 123.1(9) . . ? N1 C4 H4 118.5 . . ? N1 C8 C7 119.7(9) . . ? N1 C8 C9 117.1(7) . . ? N1 Re1 N2 78.5(2) . . ? N2 C10 C11 109.6(7) . . ? N2 C10 H10A 109.7 . . ? N2 C10 H10B 109.7 . . ? N2 C16 H16A 108.8 . . ? N2 C16 H16B 108.8 . . ? N2 C9 H9A 108 . . ? N2 C9 H9B 108 . . ? N3 C11 C10 115.2(7) . . ? N3 C11 C12 123.0(9) . . ? N3 C15 C14 122.4(10) . . ? N3 C15 H15 118.8 . . ? N3 Re1 N1 80.2(3) . . ? N3 Re1 N2 76.8(3) . . ? N4 C17 C16 122.9(7) . . ? N4 C17 C18 106.2(8) . . ? N4 N5 N6 108.2(7) . . ? N5 N4 C17 109.4(7) . . ? N5 N6 C18 110.4(7) . . ? N5 N6 C19 121.2(8) . . ? N6 C18 C17 105.8(8) . . ? N6 C18 H18 127.1 . . ? N6 C19 C20 112.1(8) . . ? N6 C19 H19A 109.2 . . ? N6 C19 H19B 109.2 . . ? N7 C29 C30 124.0(9) . . ? N7 C29 H29 118 . . ? N7 C33 C32 120.1(8) . . ? N7 C33 C34 118.0(7) . . ? N7 Re2 N8 79.1(2) . . ? N7 Re2 N9 79.2(2) . . ? N8 C34 H34A 108.3 . . ? N8 C34 H34B 108.3 . . ? N8 C35 H35A 109.3 . . ? N8 C35 H35B 109.3 . . ? N8 C41 H41A 108.9 . . ? N8 C41 H41B 108.9 . . ? N9 C36 C35 115.4(7) . . ? N9 C36 C37 119.9(8) . . ? N9 C40 C39 122.5(9) . . ? N9 C40 H40 118.8 . . ? N9 Re2 N8 76.5(2) . . ? N10 C42 C41 122.1(7) . . ? N10 N11 N12 106.4(7) . . ? N11 N10 C42 109.6(7) . . ? N11 N12 C43 111.5(7) . . ? N11 N12 C44A 119.7(8) . . ? N12 C43 C42 105.8(8) . . ? N12 C43 H43 127.1 . . ? N12 C44A H44A 109.5 . . ? N12 C44A H44B 109.5 . . ? O1 C1 Re1 175.5(8) . . ? O2 C2 Re1 177.8(8) . . ? O3 C3 Re1 177.6(8) . . ? O4 C26 Re2 176.7(7) . . ? O5 C27 Re2 178.7(8) . . ? O6 C28 Re2 178.7(7) . . ? O7 S1 C51 101.9(6) . . ? O7 S1 O8 114.7(6) . . ? O8 S1 C51 102.1(6) . . ? O9 S1 C51 103.8(5) . . ? O9 S1 O7 117.2(7) . . ? O9 S1 O8 114.3(7) . . ? O10 S2 C52 102.2(9) . . ? O10 S2 O11 108.6(9) . . ? O11 S2 C52 106.3(8) . . ? O12 S2 C52 104.3(9) . . ? O12 S2 O10 118.8(11) . . ? O12 S2 O11 115.0(10) . . ? # END data_7 _database_code_depnum_ccdc_archive 'CCDC 751746' #TrackingRef 'ccdc_deposit_Benny.cif' _audit_creation_date 2009-02-05T01:15:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C27 H21 Cl F3 N8 O6 Re' _chemical_formula_moiety 'C27 H21 F3 N8 O6 Re, Cl' _chemical_formula_weight 832.17 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' _cell_length_a 31.824(4) _cell_length_b 11.2317(12) _cell_length_c 16.0096(17) _cell_angle_alpha 90 _cell_angle_beta 90.604(5) _cell_angle_gamma 90 _cell_volume 5722.1(11) _cell_formula_units_Z 8 _cell_measurement_temperature 210(1) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.33 _cell_measurement_reflns_used 9853 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.932 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3248 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.035 _exptl_crystal_density_meas 1.932 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.419 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.769 _exptl_absorpt_correction_T_max 0.851 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 210(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.116 _diffrn_reflns_av_unetI/netI 0.0933 _diffrn_reflns_number 17938 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 5011 _reflns_number_gt 3229 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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. A CIF-check reported level-B alert and level-C alerts: 1. level B "Short Inter D...A Contact O2 .. O2" The reported short contact is crystal structures of Re-CO coordination compounds (RCCs). In particular, a search of the Cambridge Structural Database (version 5.30, November 2008) (CSD) revealed 428 structures with such a short contact (for examples see CCDC reference codes GIPSON01,HEKCEF, JIJZOR, MIVDOK, NILFEU, PATWEM, PIWHOT, RAXPOW, WAWSUI,YANJUS,YURJOK). The CSD was searched for RCCs with Re-CO...OC-Re intermolecular contacts that are within the sum of VdW radii (+0.00 A). The search was restricted to error-free and non-disordered structurs with determined 3D coordinates and R factors less than 0.05. 2. level C "Ueq as Compared to Neighbors for C27" Atoms C27 represents the carbon atoms of a CF3 group. The reported large Ueq, as compared to the F atoms, is a consequence of a substantial thermal motion of the CF3-group. No outstanding residual electron density in the Fourier map was found to be attributed to a CF3 two-fold rotational disorder. ; _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^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5011 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0636 _refine_ls_goodness_of_fit_ref 0.96 _refine_ls_restrained_S_all 0.96 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.341 _refine_diff_density_min -0.803 _refine_diff_density_rms 0.149 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Re Re -1.0185 7.231 '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' 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 C1 C 0.3866(2) 0.5735(7) 0.0942(4) 0.0364(19) Uani 1 1 d . . . C2 C 0.4300(2) 0.3987(7) 0.1675(4) 0.0424(18) Uani 1 1 d . . . C3 C 0.3470(2) 0.4148(7) 0.1941(4) 0.0331(17) Uani 1 1 d . . . C4 C 0.4072(2) 0.1323(7) 0.1153(4) 0.043(2) Uani 1 1 d . . . C5 C 0.4055(2) 0.0129(7) 0.0995(4) 0.0426(19) Uani 1 1 d . . . C6 C 0.3740(2) -0.0295(7) 0.0500(4) 0.0426(19) Uani 1 1 d . . . C7 C 0.3456(2) 0.0460(7) 0.0136(4) 0.0366(18) Uani 1 1 d . . . C8 C 0.3487(2) 0.1656(7) 0.0306(3) 0.0313(17) Uani 1 1 d . . . C9 C 0.3166(2) 0.2528(6) -0.0006(4) 0.0345(18) Uani 1 1 d . . . C10 C 0.34450(19) 0.4254(6) -0.0763(3) 0.0351(18) Uani 1 1 d . . . C11 C 0.38904(19) 0.3930(6) -0.0904(4) 0.0283(15) Uani 1 1 d . . . C12 C 0.4055(2) 0.3762(6) -0.1688(4) 0.041(2) Uani 1 1 d . . . C13 C 0.4483(2) 0.3596(7) -0.1775(4) 0.053(2) Uani 1 1 d . . . C14 C 0.4735(2) 0.3565(7) -0.1075(5) 0.052(2) Uani 1 1 d . . . C15 C 0.4553(2) 0.3696(6) -0.0310(4) 0.043(2) Uani 1 1 d . . . C16 C 0.2882(2) 0.4459(6) 0.0262(4) 0.0352(18) Uani 1 1 d . . . C17 C 0.29166(18) 0.5759(6) 0.0456(4) 0.0311(17) Uani 1 1 d . . . C18 C 0.28302(19) 0.6322(7) 0.1202(4) 0.0325(18) Uani 1 1 d . . . C19 C 0.2803(2) 0.8484(6) 0.1592(4) 0.0355(17) Uani 1 1 d . . . C20 C 0.3182(2) 0.8731(7) 0.2147(4) 0.0373(19) Uani 1 1 d . . . C21 C 0.3512(2) 1.0421(6) 0.2920(4) 0.0326(17) Uani 1 1 d . . . C22 C 0.3428(2) 1.1568(6) 0.3195(4) 0.0374(18) Uani 1 1 d . . . C23 C 0.3735(2) 1.2196(7) 0.3618(4) 0.0451(19) Uani 1 1 d . . . C24 C 0.4121(2) 1.1700(7) 0.3774(4) 0.0396(19) Uani 1 1 d . . . C25 C 0.4205(2) 1.0544(7) 0.3516(4) 0.0388(19) Uani 1 1 d . . . C26 C 0.3898(2) 0.9896(6) 0.3086(4) 0.0376(18) Uani 1 1 d . . . C27 C 0.4630(3) 0.9953(8) 0.3636(6) 0.056(2) Uani 1 1 d . . . Cl1 Cl 0.25593(5) 0.17603(17) 0.17116(9) 0.0441(5) Uani 1 1 d . . . F1 F 0.46796(12) 0.9069(5) 0.3077(3) 0.0711(13) Uani 1 1 d . . . F2 F 0.49460(14) 1.0706(5) 0.3495(3) 0.0915(17) Uani 1 1 d . . . F3 F 0.46826(15) 0.9466(5) 0.4374(3) 0.0848(17) Uani 1 1 d . . . H4 H 0.4284 0.1609 0.1502 0.051 Uiso 1 1 calc R . . H5 H 0.4255 -0.0383 0.1223 0.051 Uiso 1 1 calc R . . H6 H 0.3717 -0.111 0.0408 0.051 Uiso 1 1 calc R . . H7 H 0.3247 0.0172 -0.022 0.044 Uiso 1 1 calc R . . H7A H 0.2976 1.0283 0.232 0.044 Uiso 1 1 calc R . . H9A H 0.2909 0.2411 0.0304 0.041 Uiso 1 1 calc R . . H9B H 0.3104 0.235 -0.0587 0.041 Uiso 1 1 calc R . . H10A H 0.3272 0.3914 -0.1205 0.042 Uiso 1 1 calc R . . H10B H 0.3416 0.5113 -0.079 0.042 Uiso 1 1 calc R . . H12 H 0.388 0.3761 -0.2156 0.05 Uiso 1 1 calc R . . H13 H 0.4598 0.3505 -0.2302 0.063 Uiso 1 1 calc R . . H14 H 0.5023 0.3458 -0.112 0.062 Uiso 1 1 calc R . . H15 H 0.4723 0.3658 0.0165 0.051 Uiso 1 1 calc R . . H16A H 0.2691 0.4364 -0.021 0.042 Uiso 1 1 calc R . . H16B H 0.2756 0.4065 0.0736 0.042 Uiso 1 1 calc R . . H18 H 0.2758 0.5969 0.1706 0.039 Uiso 1 1 calc R . . H19A H 0.2561 0.8323 0.1938 0.043 Uiso 1 1 calc R . . H19B H 0.2741 0.9184 0.1258 0.043 Uiso 1 1 calc R . . H22 H 0.3166 1.1911 0.3093 0.045 Uiso 1 1 calc R . . H23 H 0.3679 1.2966 0.3801 0.054 Uiso 1 1 calc R . . H26 H 0.3951 0.9121 0.2913 0.045 Uiso 1 1 calc R . . N1 N 0.37927(15) 0.2109(5) 0.0824(3) 0.0285(13) Uani 1 1 d . . . N2 N 0.32897(16) 0.3825(5) 0.0061(3) 0.0288(13) Uani 1 1 d . . . N3 N 0.41373(16) 0.3878(5) -0.0217(3) 0.0299(13) Uani 1 1 d . . . N4 N 0.30077(16) 0.6604(5) -0.0114(3) 0.0350(14) Uani 1 1 d . . . N5 N 0.29767(16) 0.7667(5) 0.0247(3) 0.0357(14) Uani 1 1 d . . . N6 N 0.28727(15) 0.7479(5) 0.1043(3) 0.0327(14) Uani 1 1 d . . . N7 N 0.31920(16) 0.9853(5) 0.2440(3) 0.0366(15) Uani 1 1 d . . . N8 N 0.4418(2) 1.2398(7) 0.4266(4) 0.0539(18) Uani 1 1 d . . . O1 O 0.39318(15) 0.6737(5) 0.0932(3) 0.0517(15) Uani 1 1 d . . . O2 O 0.46008(16) 0.3965(6) 0.2093(3) 0.0771(18) Uani 1 1 d . . . O3 O 0.32603(15) 0.4255(5) 0.2517(3) 0.0475(14) Uani 1 1 d . . . O4 O 0.34474(15) 0.7979(5) 0.2304(3) 0.0509(14) Uani 1 1 d . . . O5 O 0.44186(19) 1.3474(6) 0.4172(3) 0.0716(17) Uani 1 1 d . . . O6 O 0.46231(17) 1.1883(5) 0.4806(4) 0.0766(18) Uani 1 1 d . . . Re1 Re 0.381693(8) 0.40302(3) 0.097046(15) 0.03137(10) 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 C1 0.029(4) 0.045(6) 0.035(4) -0.008(4) 0.000(3) -0.007(4) C2 0.040(4) 0.043(5) 0.044(4) -0.005(4) -0.009(3) 0.002(4) C3 0.036(4) 0.034(5) 0.029(4) 0.002(4) -0.005(3) -0.007(4) C4 0.039(5) 0.047(6) 0.043(4) 0.013(4) -0.002(3) 0.012(4) C5 0.035(5) 0.035(5) 0.057(5) 0.017(4) -0.002(4) 0.014(4) C6 0.047(5) 0.030(5) 0.051(4) -0.003(4) 0.008(4) 0.012(4) C7 0.051(5) 0.024(4) 0.035(4) -0.004(3) 0.006(3) -0.005(4) C8 0.027(4) 0.040(5) 0.027(4) 0.000(3) 0.003(3) 0.000(4) C9 0.038(4) 0.032(5) 0.033(4) -0.007(3) -0.010(3) 0.000(4) C10 0.036(4) 0.038(5) 0.031(4) 0.005(3) -0.001(3) 0.002(4) C11 0.033(4) 0.017(4) 0.035(4) 0.002(3) -0.006(3) 0.003(4) C12 0.051(5) 0.038(6) 0.036(4) 0.001(3) 0.010(3) 0.007(4) C13 0.052(5) 0.058(6) 0.049(5) 0.011(4) 0.019(4) 0.010(4) C14 0.033(4) 0.066(6) 0.057(5) 0.005(4) 0.012(4) 0.009(4) C15 0.034(5) 0.045(6) 0.048(4) 0.005(4) -0.010(4) 0.007(4) C16 0.036(4) 0.028(5) 0.042(4) -0.001(3) -0.008(3) 0.002(3) C17 0.027(4) 0.026(5) 0.040(4) 0.005(3) -0.011(3) 0.005(3) C18 0.026(4) 0.037(5) 0.034(4) 0.009(3) 0.003(3) 0.002(3) C19 0.035(4) 0.031(4) 0.039(4) -0.003(3) -0.006(3) 0.001(4) C20 0.036(4) 0.033(6) 0.042(4) 0.003(4) -0.008(3) 0.003(4) C21 0.042(5) 0.030(5) 0.026(4) 0.004(3) -0.006(3) 0.001(4) C22 0.039(4) 0.030(5) 0.043(4) -0.004(4) -0.013(3) 0.013(4) C23 0.054(5) 0.031(5) 0.049(4) -0.008(4) -0.008(4) 0.007(4) C24 0.040(5) 0.037(6) 0.042(4) 0.003(4) -0.010(4) -0.007(4) C25 0.032(4) 0.040(5) 0.045(4) -0.003(4) -0.010(3) 0.006(4) C26 0.036(4) 0.028(5) 0.049(4) -0.005(3) -0.004(3) 0.004(4) C27 0.048(6) 0.040(6) 0.079(6) -0.021(5) 0.002(5) -0.002(5) Cl1 0.0460(11) 0.0463(13) 0.0397(9) 0.0023(9) -0.0087(8) 0.0052(10) F1 0.045(3) 0.068(3) 0.100(3) -0.023(3) 0.000(2) 0.014(3) F2 0.034(3) 0.091(5) 0.149(4) -0.014(4) -0.002(3) -0.013(3) F3 0.084(4) 0.079(4) 0.091(4) 0.008(3) -0.037(3) 0.024(3) N1 0.028(3) 0.025(3) 0.032(3) -0.006(3) 0.001(2) -0.001(3) N2 0.038(3) 0.021(4) 0.028(3) 0.004(2) -0.004(2) 0.001(3) N3 0.030(3) 0.018(3) 0.042(3) 0.001(3) -0.005(2) 0.001(3) N4 0.035(3) 0.030(4) 0.040(3) 0.005(3) -0.002(3) 0.007(3) N5 0.035(3) 0.028(4) 0.044(4) 0.004(3) -0.004(3) 0.003(3) N6 0.033(3) 0.035(4) 0.030(3) 0.001(3) -0.003(3) 0.002(3) N7 0.032(3) 0.037(4) 0.040(3) 0.000(3) -0.013(3) 0.002(3) N8 0.056(4) 0.046(5) 0.060(4) -0.008(4) -0.014(3) 0.000(4) O1 0.056(4) 0.026(4) 0.073(3) -0.006(3) 0.003(3) -0.012(3) O2 0.055(3) 0.102(5) 0.073(4) -0.025(4) -0.036(3) 0.019(4) O3 0.060(3) 0.048(4) 0.035(3) -0.001(3) -0.001(2) -0.002(3) O4 0.043(3) 0.039(3) 0.069(3) -0.013(3) -0.024(3) 0.007(3) O5 0.087(4) 0.037(4) 0.090(4) -0.002(3) -0.018(3) -0.018(4) O6 0.068(4) 0.065(5) 0.096(4) -0.014(4) -0.042(3) -0.004(4) Re1 0.03275(16) 0.02854(17) 0.03265(15) -0.00129(16) -0.00814(10) 0.00144(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 O2 1.162(7) . ? C3 O3 1.151(7) . ? C4 C5 1.365(10) . ? C4 H4 0.93 . ? C5 H5 0.93 . ? C6 C5 1.358(9) . ? C6 H6 0.93 . ? C7 C6 1.364(9) . ? C7 C8 1.374(9) . ? C7 H7 0.93 . ? C8 C9 1.497(8) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C10 1.483(8) . ? C11 C12 1.378(8) . ? C12 H12 0.93 . ? C13 C12 1.381(9) . ? C13 C14 1.371(9) . ? C13 H13 0.93 . ? C14 H14 0.93 . ? C15 C14 1.367(9) . ? C15 H15 0.93 . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C16 1.496(9) . ? C17 C18 1.382(8) . ? C18 H18 0.93 . ? C18 N6 1.331(8) . ? C19 C20 1.518(8) . ? C19 H19A 0.97 . ? C19 H19B 0.97 . ? C19 N6 1.449(8) . ? C21 C26 1.387(8) . ? C21 N7 1.421(8) . ? C22 C21 1.388(9) . ? C22 C23 1.377(9) . ? C22 H22 0.93 . ? C23 H23 0.93 . ? C24 C23 1.369(9) . ? C24 C25 1.390(9) . ? C24 N8 1.455(8) . ? C25 C26 1.395(8) . ? C25 C27 1.517(10) . ? C26 H26 0.93 . ? F1 C27 1.347(8) . ? F2 C27 1.335(9) . ? F3 C27 1.311(9) . ? N1 C4 1.355(8) . ? N1 C8 1.370(7) . ? N2 C10 1.493(7) . ? N2 C16 1.517(8) . ? N2 C9 1.513(8) . ? N3 C11 1.347(7) . ? N3 C15 1.348(8) . ? N4 C17 1.350(8) . ? N5 N4 1.330(7) . ? N5 N6 1.337(7) . ? N7 C20 1.344(8) . ? N7 H7A 0.86 . ? O1 C1 1.144(8) . ? O4 C20 1.218(7) . ? O5 N8 1.218(7) . ? O6 N8 1.223(7) . ? Re1 C1 1.922(8) . ? Re1 C2 1.898(6) . ? Re1 C3 1.920(7) . ? Re1 N1 2.172(6) . ? Re1 N2 2.222(4) . ? Re1 N3 2.173(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Re1 N1 172.0(2) . . ? C1 Re1 N2 98.6(2) . . ? C1 Re1 N3 91.1(2) . . ? C2 Re1 C1 88.5(3) . . ? C2 Re1 C3 89.4(3) . . ? C2 Re1 N1 93.8(3) . . ? C2 Re1 N2 171.2(3) . . ? C2 Re1 N3 97.6(2) . . ? C3 Re1 C1 89.9(3) . . ? C3 Re1 N1 97.8(3) . . ? C3 Re1 N2 95.8(2) . . ? C3 Re1 N3 172.9(2) . . ? C4 C5 H5 120.7 . . ? C4 N1 C8 116.9(6) . . ? C4 N1 Re1 125.7(4) . . ? C5 C4 H4 118.5 . . ? C5 C6 C7 120.8(7) . . ? C5 C6 H6 119.6 . . ? C6 C5 C4 118.7(7) . . ? C6 C5 H5 120.7 . . ? C6 C7 C8 118.5(7) . . ? C6 C7 H7 120.7 . . ? C7 C6 H6 119.6 . . ? C7 C8 C9 121.8(6) . . ? C8 C7 H7 120.7 . . ? C8 C9 H9A 108.4 . . ? C8 C9 H9B 108.4 . . ? C8 C9 N2 115.5(5) . . ? C8 N1 Re1 117.3(4) . . ? C9 N2 C16 104.1(5) . . ? C9 N2 Re1 109.9(3) . . ? C10 N2 C16 109.1(4) . . ? C10 N2 C9 109.7(5) . . ? C10 N2 Re1 106.9(3) . . ? C11 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C11 C10 N2 112.4(5) . . ? C11 C12 C13 119.7(6) . . ? C11 C12 H12 120.2 . . ? C11 N3 C15 118.7(5) . . ? C11 N3 Re1 115.9(4) . . ? C12 C11 C10 123.1(5) . . ? C12 C13 H13 120.4 . . ? C13 C12 H12 120.2 . . ? C13 C14 H14 120.7 . . ? C14 C13 C12 119.3(6) . . ? C14 C13 H13 120.4 . . ? C14 C15 H15 118.6 . . ? C15 C14 C13 118.7(6) . . ? C15 C14 H14 120.7 . . ? C15 N3 Re1 125.4(4) . . ? C16 N2 Re1 117.0(3) . . ? C17 C16 H16A 108.2 . . ? C17 C16 H16B 108.2 . . ? C17 C16 N2 116.2(5) . . ? C17 C18 H18 127.5 . . ? C18 C17 C16 127.7(6) . . ? C18 N6 C19 128.9(6) . . ? C18 N6 N5 111.3(6) . . ? C20 C19 H19A 109.3 . . ? C20 C19 H19B 109.3 . . ? C20 N7 C21 128.6(6) . . ? C20 N7 H7A 115.7 . . ? C21 C22 H22 120.2 . . ? C21 C26 C25 119.2(7) . . ? C21 C26 H26 120.4 . . ? C21 N7 H7A 115.7 . . ? C22 C21 N7 116.8(6) . . ? C22 C23 H23 119.6 . . ? C23 C22 C21 119.6(6) . . ? C23 C22 H22 120.2 . . ? C23 C24 C25 120.1(6) . . ? C23 C24 N8 117.2(7) . . ? C24 C23 C22 120.7(7) . . ? C24 C23 H23 119.6 . . ? C24 C25 C26 119.9(6) . . ? C24 C25 C27 123.1(6) . . ? C25 C24 N8 122.5(6) . . ? C25 C26 H26 120.4 . . ? C26 C21 C22 120.5(6) . . ? C26 C21 N7 122.7(6) . . ? C26 C25 C27 117.0(7) . . ? F1 C27 C25 110.4(6) . . ? F2 C27 C25 111.9(7) . . ? F2 C27 F1 105.2(7) . . ? F3 C27 C25 113.7(7) . . ? F3 C27 F1 106.1(7) . . ? F3 C27 F2 109.1(7) . . ? H10A C10 H10B 107.9 . . ? H16A C16 H16B 107.4 . . ? H19A C19 H19B 107.9 . . ? H9A C9 H9B 107.5 . . ? N1 C4 C5 122.9(7) . . ? N1 C4 H4 118.5 . . ? N1 C8 C7 122.1(6) . . ? N1 C8 C9 115.9(6) . . ? N1 Re1 N2 78.50(18) . . ? N1 Re1 N3 81.02(18) . . ? N2 C10 H10A 109.1 . . ? N2 C10 H10B 109.1 . . ? N2 C16 H16A 108.2 . . ? N2 C16 H16B 108.2 . . ? N2 C9 H9A 108.4 . . ? N2 C9 H9B 108.4 . . ? N3 C11 C10 115.9(5) . . ? N3 C11 C12 120.9(6) . . ? N3 C15 C14 122.7(6) . . ? N3 C15 H15 118.6 . . ? N3 Re1 N2 77.10(18) . . ? N4 C17 C16 124.2(6) . . ? N4 C17 C18 108.0(6) . . ? N4 N5 N6 107.0(5) . . ? N5 N4 C17 108.7(5) . . ? N5 N6 C19 119.7(6) . . ? N6 C18 C17 105.1(6) . . ? N6 C18 H18 127.5 . . ? N6 C19 C20 111.8(5) . . ? N6 C19 H19A 109.3 . . ? N6 C19 H19B 109.3 . . ? N7 C20 C19 113.0(6) . . ? O1 C1 Re1 174.2(6) . . ? O2 C2 Re1 178.7(6) . . ? O3 C3 Re1 177.9(7) . . ? O4 C20 C19 122.6(7) . . ? O4 C20 N7 124.3(6) . . ? O5 N8 C24 118.0(7) . . ? O5 N8 O6 123.7(7) . . ? O6 N8 C24 117.8(7) . . ? # END