# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yi-Hung Liu' _publ_contact_author_email yuliu@ntu.edu.tw loop_ _publ_author_name 'Shiuh-Tzung Liu' 'Jwu-Ting Chen' data_ic14259 _database_code_depnum_ccdc_archive 'CCDC 848936' #TrackingRef '- ic14259-3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H6 N2 O9 Re2' _chemical_formula_weight 694.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9466(2) _cell_length_b 8.7775(2) _cell_length_c 12.6693(3) _cell_angle_alpha 99.095(2) _cell_angle_beta 90.065(2) _cell_angle_gamma 101.329(2) _cell_volume 855.11(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 12979 _cell_measurement_theta_min 3.0292 _cell_measurement_theta_max 30.1847 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 14.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.18645 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19399 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3933 _reflns_number_gt 3368 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0441P)^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_number_reflns 3933 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0625 _refine_ls_wR_factor_gt 0.0608 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 Re1 Re 0.38492(2) 0.253114(19) 0.833249(13) 0.03209(7) Uani 1 1 d . . . Re2 Re 0.25905(3) 0.31060(2) 0.616986(14) 0.04101(7) Uani 1 1 d . . . O1 O 0.6803(5) 0.5392(4) 0.8245(3) 0.0677(11) Uani 1 1 d . . . O2 O 0.1596(6) 0.4847(5) 0.9372(4) 0.0725(12) Uani 1 1 d . . . O3 O 0.5275(6) 0.1991(5) 1.0458(3) 0.0686(11) Uani 1 1 d . . . O4 O 0.5808(5) 0.0208(5) 0.6972(4) 0.0759(12) Uani 1 1 d . . . O6 O 0.1259(9) 0.3664(7) 0.4010(4) 0.120(2) Uani 1 1 d . . . O7 O -0.0917(6) 0.3211(6) 0.7248(4) 0.0901(14) Uani 1 1 d . . . O8 O 0.1601(7) -0.0561(5) 0.5694(4) 0.0874(15) Uani 1 1 d . . . O9 O 0.6276(6) 0.2924(6) 0.5404(4) 0.0886(15) Uani 1 1 d . . . O10 O 0.3793(7) 0.6665(5) 0.7074(3) 0.0841(14) Uani 1 1 d . . . N1 N 0.1863(5) -0.0883(4) 0.8406(4) 0.0527(10) Uani 1 1 d . . . H1A H 0.2836 -0.1175 0.8362 0.063 Uiso 1 1 calc R . . N2 N 0.0050(5) 0.0586(5) 0.8460(4) 0.0571(11) Uani 1 1 d . . . H2A H -0.0356 0.1430 0.8491 0.068 Uiso 1 1 calc R . . C1 C 0.5743(6) 0.4334(5) 0.8260(4) 0.0438(10) Uani 1 1 d . . . C2 C 0.2418(6) 0.4009(5) 0.8997(4) 0.0416(10) Uani 1 1 d . . . C3 C 0.4726(6) 0.2186(6) 0.9658(4) 0.0427(10) Uani 1 1 d . . . C4 C 0.5098(6) 0.1048(5) 0.7465(4) 0.0452(11) Uani 1 1 d . . . C5 C 0.1718(5) 0.0580(5) 0.8386(3) 0.0349(9) Uani 1 1 d . . . C6 C 0.0249(7) -0.1979(6) 0.8507(5) 0.0558(13) Uani 1 1 d . . . H6A H 0.0232 -0.2391 0.9174 0.067 Uiso 1 1 calc R . . H6B H 0.0050 -0.2848 0.7915 0.067 Uiso 1 1 calc R . . C7 C -0.1032(7) -0.0953(6) 0.8485(5) 0.0626(15) Uani 1 1 d . . . H7A H -0.1786 -0.1291 0.7854 0.075 Uiso 1 1 calc R . . H7B H -0.1718 -0.0945 0.9118 0.075 Uiso 1 1 calc R . . C8 C 0.1760(9) 0.3453(7) 0.4815(4) 0.0670(17) Uani 1 1 d . . . C9 C 0.0362(7) 0.3171(6) 0.6843(4) 0.0542(12) Uani 1 1 d . . . C10 C 0.1954(7) 0.0765(6) 0.5862(4) 0.0567(13) Uani 1 1 d . . . C11 C 0.4952(8) 0.2994(6) 0.5679(4) 0.0568(13) Uani 1 1 d . . . C12 C 0.3346(7) 0.5371(6) 0.6733(4) 0.0523(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.02861(10) 0.03014(10) 0.03693(10) 0.00664(7) -0.00128(7) 0.00341(7) Re2 0.05103(12) 0.03558(11) 0.03448(11) 0.00685(8) -0.00383(8) 0.00298(8) O1 0.055(2) 0.050(2) 0.088(3) 0.0080(19) 0.007(2) -0.0124(18) O2 0.069(3) 0.073(3) 0.079(3) 0.001(2) 0.015(2) 0.032(2) O3 0.074(3) 0.077(3) 0.059(2) 0.015(2) -0.025(2) 0.022(2) O4 0.071(3) 0.057(2) 0.105(3) 0.005(2) 0.023(2) 0.032(2) O6 0.183(6) 0.103(4) 0.066(3) 0.036(3) -0.050(4) -0.009(4) O7 0.057(3) 0.109(4) 0.120(4) 0.045(3) 0.019(3) 0.036(3) O8 0.106(4) 0.040(2) 0.105(4) -0.003(2) -0.022(3) 0.000(2) O9 0.074(3) 0.107(4) 0.090(3) 0.029(3) 0.038(3) 0.019(3) O10 0.135(4) 0.039(2) 0.073(3) 0.002(2) -0.009(3) 0.012(2) N1 0.041(2) 0.034(2) 0.084(3) 0.014(2) -0.001(2) 0.0054(17) N2 0.036(2) 0.050(2) 0.091(3) 0.029(2) 0.009(2) 0.0085(18) C1 0.036(2) 0.039(2) 0.054(3) 0.005(2) 0.0033(19) 0.003(2) C2 0.036(2) 0.041(2) 0.047(2) 0.0053(19) 0.0029(19) 0.008(2) C3 0.039(2) 0.042(2) 0.048(3) 0.013(2) -0.006(2) 0.0055(19) C4 0.038(2) 0.039(2) 0.060(3) 0.010(2) 0.007(2) 0.008(2) C5 0.037(2) 0.034(2) 0.035(2) 0.0095(17) -0.0021(17) 0.0060(17) C6 0.055(3) 0.041(3) 0.066(3) 0.020(2) -0.006(2) -0.010(2) C7 0.044(3) 0.055(3) 0.087(4) 0.024(3) 0.001(3) -0.006(2) C8 0.095(5) 0.057(3) 0.044(3) 0.016(2) -0.019(3) -0.002(3) C9 0.053(3) 0.051(3) 0.065(3) 0.023(2) -0.008(2) 0.012(2) C10 0.062(3) 0.047(3) 0.056(3) 0.001(2) -0.010(2) 0.005(3) C11 0.068(4) 0.057(3) 0.044(3) 0.012(2) 0.008(2) 0.005(3) C12 0.073(3) 0.042(3) 0.041(2) 0.009(2) -0.001(2) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C3 1.908(4) . ? Re1 C1 1.972(4) . ? Re1 C2 1.980(5) . ? Re1 C4 1.986(5) . ? Re1 C5 2.169(4) . ? Re1 Re2 3.0645(3) . ? Re2 C8 1.927(5) . ? Re2 C9 1.973(6) . ? Re2 C12 1.976(5) . ? Re2 C10 1.992(5) . ? Re2 C11 1.994(6) . ? O1 C1 1.127(5) . ? O2 C2 1.128(6) . ? O3 C3 1.153(6) . ? O4 C4 1.128(6) . ? O6 C8 1.149(6) . ? O7 C9 1.144(7) . ? O8 C10 1.127(6) . ? O9 C11 1.118(7) . ? O10 C12 1.135(6) . ? N1 C5 1.316(5) . ? N1 C6 1.463(6) . ? N1 H1A 0.8600 . ? N2 C5 1.330(6) . ? N2 C7 1.457(6) . ? N2 H2A 0.8600 . ? C6 C7 1.489(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 Re1 C1 92.1(2) . . ? C3 Re1 C2 94.8(2) . . ? C1 Re1 C2 89.40(19) . . ? C3 Re1 C4 93.5(2) . . ? C1 Re1 C4 91.93(19) . . ? C2 Re1 C4 171.49(19) . . ? C3 Re1 C5 89.34(17) . . ? C1 Re1 C5 178.31(17) . . ? C2 Re1 C5 89.64(17) . . ? C4 Re1 C5 88.82(17) . . ? C3 Re1 Re2 177.66(15) . . ? C1 Re1 Re2 86.16(14) . . ? C2 Re1 Re2 86.75(13) . . ? C4 Re1 Re2 84.95(14) . . ? C5 Re1 Re2 92.40(10) . . ? C8 Re2 C9 92.9(3) . . ? C8 Re2 C12 94.3(2) . . ? C9 Re2 C12 89.0(2) . . ? C8 Re2 C10 96.0(2) . . ? C9 Re2 C10 89.8(2) . . ? C12 Re2 C10 169.7(2) . . ? C8 Re2 C11 94.8(3) . . ? C9 Re2 C11 172.3(2) . . ? C12 Re2 C11 90.4(2) . . ? C10 Re2 C11 89.5(2) . . ? C8 Re2 Re1 179.0(2) . . ? C9 Re2 Re1 86.23(14) . . ? C12 Re2 Re1 86.09(14) . . ? C10 Re2 Re1 83.63(15) . . ? C11 Re2 Re1 86.09(15) . . ? C5 N1 C6 115.2(4) . . ? C5 N1 H1A 122.4 . . ? C6 N1 H1A 122.4 . . ? C5 N2 C7 114.5(4) . . ? C5 N2 H2A 122.7 . . ? C7 N2 H2A 122.7 . . ? O1 C1 Re1 177.8(4) . . ? O2 C2 Re1 179.6(5) . . ? O3 C3 Re1 179.1(5) . . ? O4 C4 Re1 179.9(5) . . ? N1 C5 N2 105.7(4) . . ? N1 C5 Re1 125.0(3) . . ? N2 C5 Re1 129.2(3) . . ? N1 C6 C7 101.9(4) . . ? N1 C6 H6A 111.4 . . ? C7 C6 H6A 111.4 . . ? N1 C6 H6B 111.4 . . ? C7 C6 H6B 111.4 . . ? H6A C6 H6B 109.3 . . ? N2 C7 C6 102.5(4) . . ? N2 C7 H7A 111.3 . . ? C6 C7 H7A 111.3 . . ? N2 C7 H7B 111.3 . . ? C6 C7 H7B 111.3 . . ? H7A C7 H7B 109.2 . . ? O6 C8 Re2 179.7(8) . . ? O7 C9 Re2 179.0(5) . . ? O8 C10 Re2 179.5(5) . . ? O9 C11 Re2 179.7(5) . . ? O10 C12 Re2 178.6(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C5 Re1 C4 33.2(4) . . . . ? N2 C5 Re1 C2 21.1(4) . . . . ? N1 C5 Re1 C4 33.2(4) . . . . ? C4 Re1 Re2 C12 -129.8(2) . . . . ? C4 Re1 Re2 C11 -39.1(2) . . . . ? C4 Re1 Re2 C10 50.8(2) . . . . ? C4 Re1 Re2 C9 141.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.676 _refine_diff_density_min -1.931 _refine_diff_density_rms 0.204 # Attachment '- ic14389-3b.cif' data_ic14389 _database_code_depnum_ccdc_archive 'CCDC 848937' #TrackingRef '- ic14389-3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 N2 O9 Re2' _chemical_formula_weight 722.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0464(2) _cell_length_b 9.3184(2) _cell_length_c 12.2154(3) _cell_angle_alpha 111.511(2) _cell_angle_beta 91.287(2) _cell_angle_gamma 96.573(2) _cell_volume 949.40(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 13826 _cell_measurement_theta_min 2.9874 _cell_measurement_theta_max 30.1286 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 12.787 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.54136 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21788 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4349 _reflns_number_gt 3602 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0245P)^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_number_reflns 4349 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0168 _refine_ls_wR_factor_ref 0.0407 _refine_ls_wR_factor_gt 0.0394 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.004 _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 Re1 Re 0.230297(13) 0.590666(14) 0.169749(10) 0.03428(5) Uani 1 1 d . . . Re2 Re 0.175969(14) 0.757715(15) 0.430486(11) 0.03641(5) Uani 1 1 d . . . O1 O 0.0309(3) 0.8087(3) 0.1144(2) 0.0675(8) Uani 1 1 d . . . O2 O -0.0608(3) 0.3782(3) 0.1728(3) 0.0663(8) Uani 1 1 d . . . O3 O 0.2860(4) 0.4284(4) -0.0909(2) 0.0759(9) Uani 1 1 d . . . O4 O 0.5019(3) 0.8482(3) 0.2165(3) 0.0825(10) Uani 1 1 d . . . O5 O 0.5202(3) 0.8197(3) 0.4789(3) 0.0751(9) Uani 1 1 d . . . O6 O 0.1354(4) 0.9074(4) 0.6962(3) 0.0932(11) Uani 1 1 d . . . O7 O -0.1657(3) 0.6981(3) 0.3569(2) 0.0670(8) Uani 1 1 d . . . O8 O 0.1694(4) 0.4192(3) 0.4227(3) 0.0734(8) Uani 1 1 d . . . O9 O 0.1946(3) 1.0547(3) 0.3684(3) 0.0652(7) Uani 1 1 d . . . N1 N 0.5006(3) 0.4912(3) 0.2767(3) 0.0505(7) Uani 1 1 d . . . H1A H 0.5304 0.5885 0.3147 0.061 Uiso 1 1 calc R . . N2 N 0.3557(3) 0.2848(3) 0.1749(3) 0.0452(7) Uani 1 1 d . . . C1 C 0.1032(4) 0.7298(4) 0.1368(3) 0.0457(8) Uani 1 1 d . . . C2 C 0.0472(4) 0.4527(4) 0.1704(3) 0.0435(8) Uani 1 1 d . . . C3 C 0.2646(4) 0.4889(4) 0.0070(3) 0.0502(9) Uani 1 1 d . . . C4 C 0.4041(4) 0.7519(4) 0.1984(3) 0.0505(9) Uani 1 1 d . . . C5 C 0.3719(3) 0.4393(4) 0.2099(3) 0.0360(7) Uani 1 1 d . . . C6 C 0.5856(5) 0.3695(5) 0.2797(4) 0.0707(12) Uani 1 1 d . . . H6A H 0.6197 0.3857 0.3598 0.085 Uiso 1 1 calc R . . H6B H 0.6706 0.3625 0.2319 0.085 Uiso 1 1 calc R . . C7 C 0.4708(4) 0.2271(4) 0.2280(4) 0.0614(11) Uani 1 1 d . . . H7A H 0.5119 0.1425 0.1691 0.074 Uiso 1 1 calc R . . H7B H 0.4319 0.1923 0.2887 0.074 Uiso 1 1 calc R . . C8 C 0.2289(4) 0.1732(4) 0.1053(4) 0.0613(10) Uani 1 1 d . . . H8A H 0.1631 0.2278 0.0755 0.074 Uiso 1 1 calc R . . H8B H 0.1734 0.1318 0.1565 0.074 Uiso 1 1 calc R . . C9 C 0.2730(6) 0.0411(5) 0.0038(4) 0.0879(15) Uani 1 1 d . . . H9A H 0.1853 -0.0269 -0.0380 0.132 Uiso 1 1 calc R . . H9B H 0.3358 -0.0157 0.0326 0.132 Uiso 1 1 calc R . . H9C H 0.3264 0.0807 -0.0484 0.132 Uiso 1 1 calc R . . C10 C 0.3948(4) 0.7951(4) 0.4607(3) 0.0504(9) Uani 1 1 d . . . C11 C 0.1484(5) 0.8521(5) 0.5963(3) 0.0605(10) Uani 1 1 d . . . C12 C -0.0420(4) 0.7179(4) 0.3829(3) 0.0430(8) Uani 1 1 d . . . C13 C 0.1712(4) 0.5424(4) 0.4264(3) 0.0475(8) Uani 1 1 d . . . C14 C 0.1868(4) 0.9493(4) 0.3933(3) 0.0428(8) 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 Re1 0.03491(8) 0.03880(8) 0.03331(7) 0.01679(6) 0.00435(5) 0.00960(5) Re2 0.03330(8) 0.04077(8) 0.03251(8) 0.01116(6) -0.00036(5) 0.00329(6) O1 0.079(2) 0.0643(17) 0.0671(18) 0.0282(14) -0.0092(15) 0.0313(15) O2 0.0467(16) 0.0612(17) 0.082(2) 0.0196(15) 0.0061(14) -0.0054(13) O3 0.093(2) 0.098(2) 0.0396(15) 0.0217(15) 0.0212(15) 0.0362(18) O4 0.065(2) 0.0663(19) 0.124(3) 0.0481(19) 0.0196(18) -0.0059(16) O5 0.0418(16) 0.0732(19) 0.095(2) 0.0178(17) -0.0184(15) -0.0011(14) O6 0.101(3) 0.122(3) 0.0357(16) 0.0016(17) 0.0030(16) 0.026(2) O7 0.0392(16) 0.089(2) 0.0607(17) 0.0157(15) -0.0017(13) 0.0037(14) O8 0.100(2) 0.0582(18) 0.077(2) 0.0420(16) 0.0141(17) 0.0101(16) O9 0.0670(19) 0.0468(15) 0.083(2) 0.0274(15) -0.0091(15) 0.0042(13) N1 0.0387(16) 0.0422(16) 0.071(2) 0.0218(15) -0.0063(15) 0.0076(13) N2 0.0383(16) 0.0415(16) 0.0588(18) 0.0210(14) 0.0004(13) 0.0104(13) C1 0.051(2) 0.047(2) 0.0398(19) 0.0152(16) 0.0015(16) 0.0114(17) C2 0.042(2) 0.0459(19) 0.0388(18) 0.0100(15) 0.0018(15) 0.0109(16) C3 0.057(2) 0.062(2) 0.038(2) 0.0218(17) 0.0116(16) 0.0231(18) C4 0.047(2) 0.047(2) 0.069(2) 0.0339(19) 0.0100(18) 0.0096(17) C5 0.0338(17) 0.0416(18) 0.0378(17) 0.0202(14) 0.0090(13) 0.0063(13) C6 0.050(2) 0.070(3) 0.106(4) 0.046(3) -0.009(2) 0.017(2) C7 0.057(2) 0.057(2) 0.079(3) 0.033(2) -0.004(2) 0.0164(19) C8 0.057(2) 0.050(2) 0.070(3) 0.013(2) -0.004(2) 0.0093(18) C9 0.105(4) 0.063(3) 0.078(3) 0.005(2) 0.001(3) 0.014(3) C10 0.046(2) 0.046(2) 0.056(2) 0.0173(17) -0.0053(17) 0.0043(17) C11 0.061(3) 0.074(3) 0.039(2) 0.0088(19) -0.0004(18) 0.017(2) C12 0.043(2) 0.048(2) 0.0355(17) 0.0115(15) 0.0043(15) 0.0066(16) C13 0.048(2) 0.056(2) 0.0431(19) 0.0241(17) 0.0048(16) 0.0043(17) C14 0.0368(19) 0.0411(19) 0.0461(19) 0.0112(16) -0.0011(15) 0.0056(15) _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 Re1 C3 1.913(3) . ? Re1 C1 1.967(4) . ? Re1 C4 1.975(4) . ? Re1 C2 1.979(4) . ? Re1 C5 2.183(3) . ? Re1 Re2 3.06895(19) . ? Re2 C11 1.924(4) . ? Re2 C10 1.973(4) . ? Re2 C13 1.984(4) . ? Re2 C14 1.990(4) . ? Re2 C12 1.997(4) . ? O1 C1 1.137(4) . ? O2 C2 1.139(4) . ? O3 C3 1.152(4) . ? O4 C4 1.141(4) . ? O5 C10 1.132(4) . ? O6 C11 1.153(4) . ? O7 C12 1.131(4) . ? O8 C13 1.131(4) . ? O9 C14 1.125(4) . ? N1 C5 1.340(4) . ? N1 C6 1.452(5) . ? N1 H1A 0.8600 . ? N2 C5 1.332(4) . ? N2 C7 1.465(4) . ? N2 C8 1.468(4) . ? C6 C7 1.509(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.492(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 C3 Re1 C1 93.03(15) . . ? C3 Re1 C4 93.49(16) . . ? C1 Re1 C4 89.38(14) . . ? C3 Re1 C2 96.86(15) . . ? C1 Re1 C2 88.49(14) . . ? C4 Re1 C2 169.53(14) . . ? C3 Re1 C5 88.00(13) . . ? C1 Re1 C5 178.91(12) . . ? C4 Re1 C5 90.21(13) . . ? C2 Re1 C5 91.73(13) . . ? C3 Re1 Re2 179.30(11) . . ? C1 Re1 Re2 86.47(10) . . ? C4 Re1 Re2 86.02(11) . . ? C2 Re1 Re2 83.62(9) . . ? C5 Re1 Re2 92.49(8) . . ? C11 Re2 C10 91.42(16) . . ? C11 Re2 C13 96.04(17) . . ? C10 Re2 C13 90.96(15) . . ? C11 Re2 C14 97.79(16) . . ? C10 Re2 C14 88.92(14) . . ? C13 Re2 C14 166.17(14) . . ? C11 Re2 C12 94.10(15) . . ? C10 Re2 C12 174.11(14) . . ? C13 Re2 C12 90.49(14) . . ? C14 Re2 C12 88.31(14) . . ? C11 Re2 Re1 176.16(13) . . ? C10 Re2 Re1 86.76(11) . . ? C13 Re2 Re1 80.61(10) . . ? C14 Re2 Re1 85.57(10) . . ? C12 Re2 Re1 87.85(9) . . ? C5 N1 C6 114.3(3) . . ? C5 N1 H1A 122.8 . . ? C6 N1 H1A 122.8 . . ? C5 N2 C7 113.5(3) . . ? C5 N2 C8 127.7(3) . . ? C7 N2 C8 118.2(3) . . ? O1 C1 Re1 178.0(3) . . ? O2 C2 Re1 177.4(3) . . ? O3 C3 Re1 179.5(4) . . ? O4 C4 Re1 178.0(3) . . ? N2 C5 N1 106.1(3) . . ? N2 C5 Re1 130.1(2) . . ? N1 C5 Re1 123.8(2) . . ? N1 C6 C7 101.4(3) . . ? N1 C6 H6A 111.5 . . ? C7 C6 H6A 111.5 . . ? N1 C6 H6B 111.5 . . ? C7 C6 H6B 111.5 . . ? H6A C6 H6B 109.3 . . ? N2 C7 C6 102.1(3) . . ? N2 C7 H7A 111.4 . . ? C6 C7 H7A 111.4 . . ? N2 C7 H7B 111.4 . . ? C6 C7 H7B 111.4 . . ? H7A C7 H7B 109.2 . . ? N2 C8 C9 113.8(4) . . ? N2 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? N2 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 Re2 178.6(3) . . ? O6 C11 Re2 178.2(4) . . ? O7 C12 Re2 178.8(3) . . ? O8 C13 Re2 179.1(3) . . ? O9 C14 Re2 177.6(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.439 _refine_diff_density_min -0.800 _refine_diff_density_rms 0.095 # Attachment 'ic14558-revised.cif' data_ic14558 _database_code_depnum_ccdc_archive 'CCDC 848938' #TrackingRef 'ic14558-revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 Br N2 O4 Re' _chemical_formula_weight 684.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 15.0972(5) _cell_length_b 20.2743(7) _cell_length_c 8.5553(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2618.65(16) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8592 _cell_measurement_theta_min 2.8736 _cell_measurement_theta_max 30.2267 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 6.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.56028 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17083 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3096 _reflns_number_gt 2440 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0379P)^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_number_reflns 3096 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0574 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _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 Re1 Re 0.095661(11) 0.7500 0.82777(2) 0.03155(7) Uani 1 2 d S . . Br1 Br 0.23715(4) 0.7500 0.65198(6) 0.06275(16) Uani 1 2 d S . . O1 O -0.0161(2) 0.7500 0.5252(4) 0.0630(10) Uani 1 2 d S . . O2 O 0.08078(19) 0.59946(14) 0.7644(4) 0.0759(10) Uani 1 1 d . . . O3 O -0.0664(3) 0.7500 1.0391(5) 0.0740(13) Uani 1 2 d S . . N1 N 0.22027(17) 0.69678(12) 1.1029(3) 0.0386(6) Uani 1 1 d . . . C1 C 0.0239(3) 0.7500 0.6378(6) 0.0421(11) Uani 1 2 d S . . C2 C 0.0918(2) 0.65209(19) 0.8010(4) 0.0463(9) Uani 1 1 d . . . C3 C -0.0065(3) 0.7500 0.9608(6) 0.0459(12) Uani 1 2 d S . . C5 C 0.1858(3) 0.7500 1.0316(5) 0.0309(9) Uani 1 2 d S . . C6 C 0.2818(3) 0.71258(15) 1.2319(4) 0.0532(9) Uani 1 1 d . . . H6A H 0.3406 0.6952 1.2116 0.064 Uiso 1 1 calc R . . H6B H 0.2605 0.6952 1.3307 0.064 Uiso 1 1 calc R . . C7 C 0.2005(2) 0.62876(14) 1.0759(4) 0.0354(7) Uani 1 1 d . . . C8 C 0.2585(2) 0.59119(16) 0.9860(4) 0.0459(8) Uani 1 1 d . . . C9 C 0.2373(2) 0.52533(16) 0.9611(4) 0.0533(9) Uani 1 1 d . . . H9A H 0.2752 0.4997 0.9005 0.064 Uiso 1 1 calc R . . C10 C 0.1629(2) 0.49681(15) 1.0223(4) 0.0513(9) Uani 1 1 d . . . C11 C 0.1099(2) 0.53430(17) 1.1191(5) 0.0474(8) Uani 1 1 d . . . H11A H 0.0608 0.5149 1.1658 0.057 Uiso 1 1 calc R . . C12 C 0.1279(2) 0.60013(16) 1.1485(4) 0.0409(8) Uani 1 1 d . . . C13 C 0.3408(2) 0.6204(2) 0.9160(5) 0.0706(12) Uani 1 1 d . . . H13A H 0.3720 0.5871 0.8584 0.106 Uiso 1 1 calc R . . H13B H 0.3781 0.6370 0.9978 0.106 Uiso 1 1 calc R . . H13C H 0.3249 0.6558 0.8469 0.106 Uiso 1 1 calc R . . C14 C 0.1406(4) 0.42582(18) 0.9843(6) 0.0838(14) Uani 1 1 d . . . H14A H 0.1849 0.4080 0.9157 0.126 Uiso 1 1 calc R . . H14B H 0.0838 0.4239 0.9340 0.126 Uiso 1 1 calc R . . H14C H 0.1389 0.4005 1.0791 0.126 Uiso 1 1 calc R . . C15 C 0.0700(3) 0.6390(2) 1.2611(5) 0.0617(11) Uani 1 1 d . . . H15A H 0.0234 0.6112 1.2995 0.093 Uiso 1 1 calc R . . H15B H 0.0448 0.6762 1.2077 0.093 Uiso 1 1 calc R . . H15C H 0.1054 0.6542 1.3472 0.093 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 Re1 0.03133(10) 0.03528(11) 0.02803(10) 0.000 -0.00164(7) 0.000 Br1 0.0554(3) 0.0874(4) 0.0455(3) 0.000 0.0190(3) 0.000 O1 0.066(2) 0.075(3) 0.048(2) 0.000 -0.022(2) 0.000 O2 0.108(3) 0.0428(16) 0.076(2) -0.0094(16) -0.0341(18) -0.0029(15) O3 0.0399(19) 0.111(4) 0.071(3) 0.000 0.014(2) 0.000 N1 0.0517(15) 0.0301(14) 0.0341(14) 0.0001(11) -0.0131(13) 0.0023(12) C1 0.040(3) 0.045(3) 0.041(3) 0.000 -0.007(2) 0.000 C2 0.050(2) 0.047(2) 0.042(2) 0.0000(16) -0.0102(16) -0.0006(16) C3 0.035(2) 0.057(3) 0.046(3) 0.000 0.001(2) 0.000 C5 0.035(2) 0.035(2) 0.023(2) 0.000 0.0007(18) 0.000 C6 0.071(2) 0.0403(19) 0.049(2) -0.0027(16) -0.028(2) 0.0029(17) C7 0.0468(17) 0.0270(15) 0.0324(16) -0.0003(13) -0.0081(15) 0.0066(14) C8 0.0479(18) 0.0445(19) 0.045(2) -0.0035(17) -0.0056(17) 0.0091(16) C9 0.065(2) 0.0400(19) 0.055(2) -0.0146(18) -0.0004(19) 0.0192(18) C10 0.069(2) 0.0293(17) 0.055(2) -0.0049(17) -0.006(2) 0.0049(17) C11 0.054(2) 0.0372(18) 0.051(2) 0.0051(16) 0.0014(18) -0.0027(16) C12 0.0526(19) 0.0345(17) 0.0355(19) 0.0004(14) -0.0018(15) 0.0073(15) C13 0.052(2) 0.077(3) 0.083(3) -0.004(2) 0.013(2) 0.005(2) C14 0.117(4) 0.034(2) 0.101(4) -0.017(2) -0.005(3) -0.001(2) C15 0.079(3) 0.052(2) 0.054(2) -0.002(2) 0.016(2) 0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C3 1.917(5) . ? Re1 C1 1.953(5) . ? Re1 C2 1.999(4) 7_575 ? Re1 C2 1.999(4) . ? Re1 C5 2.213(4) . ? Re1 Br1 2.6124(6) . ? O1 C1 1.137(5) . ? O2 C2 1.125(4) . ? O3 C3 1.126(6) . ? N1 C5 1.344(3) . ? N1 C7 1.430(4) . ? N1 C6 1.478(4) . ? C5 N1 1.344(3) 7_575 ? C6 C6 1.517(6) 7_575 ? C7 C12 1.387(5) . ? C7 C8 1.392(4) . ? C8 C9 1.389(4) . ? C8 C13 1.501(5) . ? C9 C10 1.368(5) . ? C10 C11 1.380(5) . ? C10 C14 1.513(5) . ? C11 C12 1.385(4) . ? C12 C15 1.520(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 C3 Re1 C1 92.8(2) . . ? C3 Re1 C2 92.54(10) . 7_575 ? C1 Re1 C2 83.60(10) . 7_575 ? C3 Re1 C2 92.54(10) . . ? C1 Re1 C2 83.60(10) . . ? C2 Re1 C2 166.4(2) 7_575 . ? C3 Re1 C5 91.53(18) . . ? C1 Re1 C5 175.70(17) . . ? C2 Re1 C5 96.21(10) 7_575 . ? C2 Re1 C5 96.21(10) . . ? C3 Re1 Br1 178.71(15) . . ? C1 Re1 Br1 88.53(14) . . ? C2 Re1 Br1 87.60(10) 7_575 . ? C2 Re1 Br1 87.60(10) . . ? C5 Re1 Br1 87.18(10) . . ? C5 N1 C7 128.3(3) . . ? C5 N1 C6 114.1(3) . . ? C7 N1 C6 117.5(2) . . ? O1 C1 Re1 178.4(4) . . ? O2 C2 Re1 168.1(3) . . ? O3 C3 Re1 180.0(5) . . ? N1 C5 N1 106.8(3) . 7_575 ? N1 C5 Re1 126.57(17) . . ? N1 C5 Re1 126.56(17) 7_575 . ? N1 C6 C6 102.51(15) . 7_575 ? C12 C7 C8 121.0(3) . . ? C12 C7 N1 119.8(3) . . ? C8 C7 N1 119.0(3) . . ? C9 C8 C7 117.8(3) . . ? C9 C8 C13 120.5(3) . . ? C7 C8 C13 121.7(3) . . ? C10 C9 C8 122.4(3) . . ? C9 C10 C11 118.3(3) . . ? C9 C10 C14 120.1(3) . . ? C11 C10 C14 121.6(4) . . ? C10 C11 C12 121.7(3) . . ? C11 C12 C7 118.5(3) . . ? C11 C12 C15 120.1(3) . . ? C7 C12 C15 121.4(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.366 _refine_diff_density_min -1.066 _refine_diff_density_rms 0.094 # Attachment 'ic15015-revised-2.cif' data_ic15015 _database_code_depnum_ccdc_archive 'CCDC 848939' #TrackingRef 'ic15015-revised-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H33 N2 O5 Re' _chemical_formula_weight 651.75 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' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0693(2) _cell_length_b 10.3030(2) _cell_length_c 23.0176(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.486(2) _cell_angle_gamma 90.00 _cell_volume 2624.99(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16578 _cell_measurement_theta_min 2.8316 _cell_measurement_theta_max 29.8912 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 4.668 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.71305 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30680 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6023 _reflns_number_gt 5352 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0314P)^2^+5.7821P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6023 _refine_ls_number_parameters 308 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0632 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.049 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.264080(11) 0.389761(12) 0.228061(5) 0.01857(5) Uani 1 1 d . . . H1 H 0.114(4) 0.367(4) 0.234(2) 0.040(13) Uiso 1 1 d . . . O1 O 0.2800(3) 0.0998(2) 0.19468(13) 0.0352(6) Uani 1 1 d . . . O2 O 0.3069(3) 0.2699(3) 0.35076(12) 0.0381(7) Uani 1 1 d . . . O3 O 0.5361(3) 0.4557(3) 0.21228(15) 0.0496(8) Uani 1 1 d . . . O4 O 0.2008(4) 0.4004(3) 0.09637(13) 0.0537(10) Uani 1 1 d . . . N1 N 0.1902(3) 0.6870(3) 0.21696(11) 0.0211(6) Uani 1 1 d . . . N2 N 0.2105(3) 0.6362(3) 0.30721(12) 0.0200(6) Uani 1 1 d . . . C1 C 0.2781(3) 0.2077(4) 0.20718(16) 0.0253(7) Uani 1 1 d . . . C2 C 0.2903(3) 0.3250(3) 0.30870(15) 0.0250(7) Uani 1 1 d . . . C3 C 0.4358(4) 0.4324(4) 0.21799(17) 0.0300(8) Uani 1 1 d . . . C4 C 0.2235(4) 0.4102(4) 0.14448(17) 0.0328(9) Uani 1 1 d . . . C5 C 0.2173(3) 0.5883(3) 0.25306(15) 0.0186(6) Uani 1 1 d . . . C6 C 0.1624(3) 0.8099(3) 0.24692(14) 0.0245(7) Uani 1 1 d . . . H6A H 0.0789 0.8390 0.2381 0.029 Uiso 1 1 calc R . . H6B H 0.2197 0.8793 0.2359 0.029 Uiso 1 1 calc R . . C7 C 0.1766(4) 0.7741(3) 0.30987(15) 0.0277(8) Uani 1 1 d . . . H7A H 0.2408 0.8264 0.3289 0.033 Uiso 1 1 calc R . . H7B H 0.1000 0.7862 0.3311 0.033 Uiso 1 1 calc R . . C8 C 0.2257(3) 0.5692(3) 0.36113(14) 0.0200(6) Uani 1 1 d . . . C9 C 0.3391(3) 0.5702(4) 0.38815(15) 0.0249(7) Uani 1 1 d . . . C10 C 0.3486(4) 0.5141(4) 0.44294(16) 0.0313(8) Uani 1 1 d . . . H10A H 0.4250 0.5139 0.4621 0.038 Uiso 1 1 calc R . . C11 C 0.2509(4) 0.4587(4) 0.47064(16) 0.0320(8) Uani 1 1 d . . . C12 C 0.1408(3) 0.4591(4) 0.44236(15) 0.0277(8) Uani 1 1 d . . . H12A H 0.0734 0.4200 0.4607 0.033 Uiso 1 1 calc R . . C13 C 0.1251(3) 0.5151(3) 0.38772(14) 0.0231(7) Uani 1 1 d . . . C14 C 0.4465(4) 0.6283(4) 0.35888(18) 0.0349(9) Uani 1 1 d . . . H14A H 0.4222 0.6625 0.3208 0.052 Uiso 1 1 calc R . . H14B H 0.5086 0.5615 0.3538 0.052 Uiso 1 1 calc R . . H14C H 0.4791 0.6988 0.3829 0.052 Uiso 1 1 calc R . . C15 C 0.2645(5) 0.4006(5) 0.53063(19) 0.0484(12) Uani 1 1 d . . . H15A H 0.3485 0.4093 0.5438 0.073 Uiso 1 1 calc R . . H15B H 0.2425 0.3085 0.5293 0.073 Uiso 1 1 calc R . . H15C H 0.2113 0.4463 0.5576 0.073 Uiso 1 1 calc R . . C16 C 0.0025(3) 0.5191(4) 0.35905(17) 0.0315(8) Uani 1 1 d . . . H16A H 0.0086 0.5623 0.3213 0.047 Uiso 1 1 calc R . . H16B H -0.0536 0.5672 0.3837 0.047 Uiso 1 1 calc R . . H16C H -0.0273 0.4303 0.3535 0.047 Uiso 1 1 calc R . . C17 C 0.1692(3) 0.6831(3) 0.15556(14) 0.0223(7) Uani 1 1 d . . . C18 C 0.0541(3) 0.6486(3) 0.13539(16) 0.0264(7) Uani 1 1 d . . . C19 C 0.0321(4) 0.6538(4) 0.07598(17) 0.0360(9) Uani 1 1 d . . . H19A H -0.0455 0.6305 0.0615 0.043 Uiso 1 1 calc R . . C20 C 0.1201(5) 0.6920(4) 0.03729(16) 0.0392(10) Uani 1 1 d . . . C21 C 0.2315(4) 0.7283(4) 0.05893(17) 0.0379(10) Uani 1 1 d . . . H21A H 0.2917 0.7565 0.0326 0.046 Uiso 1 1 calc R . . C22 C 0.2587(4) 0.7252(3) 0.11792(15) 0.0277(8) Uani 1 1 d . . . C23 C -0.0423(4) 0.6035(4) 0.17636(19) 0.0337(9) Uani 1 1 d . . . H23A H -0.1162 0.5837 0.1543 0.051 Uiso 1 1 calc R . . H23B H -0.0589 0.6720 0.2047 0.051 Uiso 1 1 calc R . . H23C H -0.0145 0.5253 0.1967 0.051 Uiso 1 1 calc R . . C24 C 0.0935(6) 0.6925(5) -0.02732(19) 0.0617(16) Uani 1 1 d . . . H24A H 0.1651 0.7218 -0.0483 0.093 Uiso 1 1 calc R . . H24B H 0.0259 0.7514 -0.0355 0.093 Uiso 1 1 calc R . . H24C H 0.0721 0.6046 -0.0400 0.093 Uiso 1 1 calc R . . C25 C 0.3810(4) 0.7653(4) 0.14055(18) 0.0383(9) Uani 1 1 d . . . H25A H 0.3832 0.7560 0.1829 0.057 Uiso 1 1 calc R . . H25B H 0.3961 0.8560 0.1302 0.057 Uiso 1 1 calc R . . H25C H 0.4432 0.7100 0.1233 0.057 Uiso 1 1 calc R . . O5 O 0.4937(10) 0.4259(10) 0.0375(4) 0.186(4) Uiso 1 1 d D A 1 H5 H 0.458(3) 0.397(4) 0.0647(9) 0.279 Uiso 1 1 d D B 1 C26 C 0.5889(10) 0.4707(11) 0.0688(5) 0.127(3) Uiso 1 1 d . A 1 H26A H 0.6499 0.4022 0.0761 0.153 Uiso 1 1 calc R A 1 H26B H 0.5636 0.5093 0.1061 0.153 Uiso 1 1 calc R A 1 C27 C 0.6300(14) 0.5638(15) 0.0302(7) 0.199(6) Uiso 1 1 d . A 1 H27A H 0.7017 0.6066 0.0466 0.299 Uiso 1 1 calc R A 1 H27B H 0.5665 0.6284 0.0234 0.299 Uiso 1 1 calc R A 1 H27C H 0.6509 0.5222 -0.0067 0.299 Uiso 1 1 calc R A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.01906(8) 0.01618(8) 0.02047(8) 0.00051(5) 0.00046(5) 0.00180(5) O1 0.0367(16) 0.0190(14) 0.0501(18) -0.0040(12) 0.0048(13) 0.0014(11) O2 0.0519(18) 0.0315(15) 0.0306(14) 0.0096(12) -0.0070(12) 0.0064(13) O3 0.0286(16) 0.055(2) 0.065(2) -0.0101(17) 0.0118(14) -0.0088(14) O4 0.101(3) 0.0326(17) 0.0275(16) -0.0097(12) -0.0166(17) 0.0209(17) N1 0.0277(15) 0.0181(14) 0.0176(13) -0.0001(11) -0.0021(11) 0.0008(11) N2 0.0251(15) 0.0184(13) 0.0164(13) -0.0001(10) -0.0022(11) 0.0022(11) C1 0.0194(17) 0.029(2) 0.0277(17) 0.0017(15) 0.0022(13) 0.0028(14) C2 0.0238(17) 0.0212(17) 0.0299(18) 0.0015(15) 0.0020(14) 0.0030(14) C3 0.030(2) 0.0253(18) 0.035(2) -0.0047(16) 0.0020(15) -0.0003(16) C4 0.050(3) 0.0196(18) 0.028(2) -0.0018(14) -0.0032(17) 0.0082(16) C5 0.0156(15) 0.0195(16) 0.0205(15) 0.0000(12) -0.0021(12) -0.0005(12) C6 0.0336(19) 0.0173(16) 0.0226(16) -0.0001(13) -0.0008(14) 0.0035(14) C7 0.041(2) 0.0170(16) 0.0246(17) -0.0014(14) -0.0052(15) 0.0023(15) C8 0.0246(17) 0.0196(16) 0.0159(14) -0.0002(12) -0.0030(12) -0.0009(13) C9 0.0249(18) 0.0281(18) 0.0216(16) 0.0022(14) -0.0032(13) -0.0019(14) C10 0.031(2) 0.039(2) 0.0240(17) 0.0027(16) -0.0071(14) -0.0005(16) C11 0.042(2) 0.032(2) 0.0223(17) 0.0071(15) -0.0012(15) -0.0001(17) C12 0.033(2) 0.0261(18) 0.0244(17) 0.0001(14) 0.0064(14) -0.0043(15) C13 0.0233(17) 0.0221(17) 0.0240(16) -0.0035(13) -0.0010(13) 0.0000(13) C14 0.0250(19) 0.050(3) 0.030(2) 0.0072(17) -0.0013(15) -0.0075(17) C15 0.057(3) 0.059(3) 0.029(2) 0.016(2) -0.002(2) -0.003(2) C16 0.0234(18) 0.039(2) 0.0321(19) -0.0054(16) -0.0023(15) -0.0044(16) C17 0.0321(18) 0.0171(16) 0.0176(15) 0.0015(12) -0.0033(13) 0.0021(13) C18 0.033(2) 0.0170(16) 0.0289(18) 0.0011(14) -0.0067(15) 0.0047(14) C19 0.052(3) 0.0223(18) 0.033(2) 0.0004(16) -0.0181(18) 0.0008(18) C20 0.072(3) 0.0232(19) 0.0216(18) 0.0033(15) -0.0111(18) -0.0026(19) C21 0.062(3) 0.027(2) 0.0239(18) 0.0042(16) 0.0048(18) -0.0072(19) C22 0.042(2) 0.0188(17) 0.0226(17) 0.0023(14) 0.0017(15) -0.0023(15) C23 0.027(2) 0.032(2) 0.043(2) -0.0011(17) -0.0022(17) 0.0012(15) C24 0.115(5) 0.044(3) 0.026(2) 0.0076(19) -0.020(3) -0.007(3) C25 0.039(2) 0.041(2) 0.035(2) 0.0005(18) 0.0057(17) -0.0111(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C1 1.943(4) . ? Re1 C3 1.966(4) . ? Re1 C4 1.983(4) . ? Re1 C2 1.991(4) . ? Re1 C5 2.188(3) . ? Re1 H1 1.68(5) . ? O1 C1 1.149(4) . ? O2 C2 1.136(4) . ? O3 C3 1.145(5) . ? O4 C4 1.138(5) . ? N1 C5 1.346(4) . ? N1 C17 1.431(4) . ? N1 C6 1.476(4) . ? N2 C5 1.343(4) . ? N2 C8 1.429(4) . ? N2 C7 1.471(4) . ? C6 C7 1.502(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.392(5) . ? C8 C9 1.396(5) . ? C9 C10 1.390(5) . ? C9 C14 1.497(5) . ? C10 C11 1.383(5) . ? C10 H10A 0.9500 . ? C11 C12 1.377(6) . ? C11 C15 1.511(5) . ? C12 C13 1.393(5) . ? C12 H12A 0.9500 . ? C13 C16 1.504(5) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.391(5) . ? C17 C18 1.399(5) . ? C18 C19 1.388(5) . ? C18 C23 1.503(6) . ? C19 C20 1.382(6) . ? C19 H19A 0.9500 . ? C20 C21 1.377(6) . ? C20 C24 1.513(5) . ? C21 C22 1.389(5) . ? C21 H21A 0.9500 . ? C22 C25 1.504(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? O5 C26 1.352(12) . ? O5 H5 0.80(2) . ? C26 C27 1.387(16) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 C1 Re1 C3 96.15(15) . . ? C1 Re1 C4 83.13(15) . . ? C3 Re1 C4 94.19(17) . . ? C1 Re1 C2 84.03(15) . . ? C3 Re1 C2 92.95(15) . . ? C4 Re1 C2 165.90(15) . . ? C1 Re1 C5 170.78(13) . . ? C3 Re1 C5 93.07(14) . . ? C4 Re1 C5 95.95(14) . . ? C2 Re1 C5 95.79(13) . . ? C1 Re1 H1 88.0(15) . . ? C3 Re1 H1 174.5(15) . . ? C4 Re1 H1 82.8(16) . . ? C2 Re1 H1 91.0(16) . . ? C5 Re1 H1 82.7(15) . . ? C5 N1 C17 128.5(3) . . ? C5 N1 C6 114.0(3) . . ? C17 N1 C6 116.9(3) . . ? C5 N2 C8 128.4(3) . . ? C5 N2 C7 114.2(3) . . ? C8 N2 C7 117.3(3) . . ? O1 C1 Re1 176.5(3) . . ? O2 C2 Re1 169.5(3) . . ? O3 C3 Re1 179.2(4) . . ? O4 C4 Re1 168.8(3) . . ? N2 C5 N1 106.3(3) . . ? N2 C5 Re1 127.1(2) . . ? N1 C5 Re1 126.6(2) . . ? N1 C6 C7 102.7(3) . . ? N1 C6 H6A 111.2 . . ? C7 C6 H6A 111.2 . . ? N1 C6 H6B 111.2 . . ? C7 C6 H6B 111.2 . . ? H6A C6 H6B 109.1 . . ? N2 C7 C6 102.8(3) . . ? N2 C7 H7A 111.2 . . ? C6 C7 H7A 111.2 . . ? N2 C7 H7B 111.2 . . ? C6 C7 H7B 111.2 . . ? H7A C7 H7B 109.1 . . ? C13 C8 C9 121.8(3) . . ? C13 C8 N2 119.1(3) . . ? C9 C8 N2 118.8(3) . . ? C10 C9 C8 117.5(3) . . ? C10 C9 C14 121.3(3) . . ? C8 C9 C14 121.2(3) . . ? C11 C10 C9 122.4(4) . . ? C11 C10 H10A 118.8 . . ? C9 C10 H10A 118.8 . . ? C12 C11 C10 118.2(3) . . ? C12 C11 C15 120.9(4) . . ? C10 C11 C15 120.8(4) . . ? C11 C12 C13 122.1(3) . . ? C11 C12 H12A 119.0 . . ? C13 C12 H12A 119.0 . . ? C8 C13 C12 117.9(3) . . ? C8 C13 C16 121.2(3) . . ? C12 C13 C16 120.8(3) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 121.6(3) . . ? C22 C17 N1 119.7(3) . . ? C18 C17 N1 118.4(3) . . ? C19 C18 C17 117.9(4) . . ? C19 C18 C23 120.7(4) . . ? C17 C18 C23 121.3(3) . . ? C20 C19 C18 121.8(4) . . ? C20 C19 H19A 119.1 . . ? C18 C19 H19A 119.1 . . ? C21 C20 C19 118.5(3) . . ? C21 C20 C24 121.4(4) . . ? C19 C20 C24 120.1(4) . . ? C20 C21 C22 122.3(4) . . ? C20 C21 H21A 118.9 . . ? C22 C21 H21A 118.9 . . ? C21 C22 C17 117.8(4) . . ? C21 C22 C25 121.3(4) . . ? C17 C22 C25 120.9(3) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C26 O5 H5 96(3) . . ? O5 C26 C27 98.8(11) . . ? O5 C26 H26A 112.0 . . ? C27 C26 H26A 112.0 . . ? O5 C26 H26B 112.0 . . ? C27 C26 H26B 112.0 . . ? H26A C26 H26B 109.7 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 C3 Re1 C1 O1 -168(5) . . . . ? C4 Re1 C1 O1 -75(5) . . . . ? C2 Re1 C1 O1 100(5) . . . . ? C5 Re1 C1 O1 10(6) . . . . ? C1 Re1 C2 O2 2.2(17) . . . . ? C3 Re1 C2 O2 -93.7(17) . . . . ? C4 Re1 C2 O2 27(2) . . . . ? C5 Re1 C2 O2 173.0(17) . . . . ? C1 Re1 C3 O3 -29(26) . . . . ? C4 Re1 C3 O3 -112(26) . . . . ? C2 Re1 C3 O3 55(26) . . . . ? C5 Re1 C3 O3 151(100) . . . . ? C1 Re1 C4 O4 6(2) . . . . ? C3 Re1 C4 O4 102(2) . . . . ? C2 Re1 C4 O4 -19(3) . . . . ? C5 Re1 C4 O4 -165(2) . . . . ? C8 N2 C5 N1 176.8(3) . . . . ? C7 N2 C5 N1 0.3(4) . . . . ? C8 N2 C5 Re1 -3.5(5) . . . . ? C7 N2 C5 Re1 -180.0(2) . . . . ? C17 N1 C5 N2 -170.9(3) . . . . ? C6 N1 C5 N2 -0.4(4) . . . . ? C17 N1 C5 Re1 9.4(5) . . . . ? C6 N1 C5 Re1 180.0(2) . . . . ? C1 Re1 C5 N2 87.5(9) . . . . ? C3 Re1 C5 N2 -94.1(3) . . . . ? C4 Re1 C5 N2 171.3(3) . . . . ? C2 Re1 C5 N2 -0.8(3) . . . . ? C1 Re1 C5 N1 -92.8(9) . . . . ? C3 Re1 C5 N1 85.5(3) . . . . ? C4 Re1 C5 N1 -9.0(3) . . . . ? C2 Re1 C5 N1 178.8(3) . . . . ? C5 N1 C6 C7 0.2(4) . . . . ? C17 N1 C6 C7 171.9(3) . . . . ? C5 N2 C7 C6 -0.2(4) . . . . ? C8 N2 C7 C6 -177.1(3) . . . . ? N1 C6 C7 N2 0.0(4) . . . . ? C5 N2 C8 C13 -90.8(4) . . . . ? C7 N2 C8 C13 85.6(4) . . . . ? C5 N2 C8 C9 95.0(4) . . . . ? C7 N2 C8 C9 -88.6(4) . . . . ? C13 C8 C9 C10 0.4(5) . . . . ? N2 C8 C9 C10 174.4(3) . . . . ? C13 C8 C9 C14 179.8(3) . . . . ? N2 C8 C9 C14 -6.2(5) . . . . ? C8 C9 C10 C11 0.0(6) . . . . ? C14 C9 C10 C11 -179.4(4) . . . . ? C9 C10 C11 C12 0.3(6) . . . . ? C9 C10 C11 C15 -179.0(4) . . . . ? C10 C11 C12 C13 -1.1(6) . . . . ? C15 C11 C12 C13 178.3(4) . . . . ? C9 C8 C13 C12 -1.1(5) . . . . ? N2 C8 C13 C12 -175.1(3) . . . . ? C9 C8 C13 C16 177.7(3) . . . . ? N2 C8 C13 C16 3.7(5) . . . . ? C11 C12 C13 C8 1.4(5) . . . . ? C11 C12 C13 C16 -177.3(4) . . . . ? C5 N1 C17 C22 -103.2(4) . . . . ? C6 N1 C17 C22 86.5(4) . . . . ? C5 N1 C17 C18 82.9(4) . . . . ? C6 N1 C17 C18 -87.4(4) . . . . ? C22 C17 C18 C19 1.8(5) . . . . ? N1 C17 C18 C19 175.6(3) . . . . ? C22 C17 C18 C23 -179.9(3) . . . . ? N1 C17 C18 C23 -6.1(5) . . . . ? C17 C18 C19 C20 -0.2(6) . . . . ? C23 C18 C19 C20 -178.4(4) . . . . ? C18 C19 C20 C21 -1.4(6) . . . . ? C18 C19 C20 C24 178.2(4) . . . . ? C19 C20 C21 C22 1.4(6) . . . . ? C24 C20 C21 C22 -178.2(4) . . . . ? C20 C21 C22 C17 0.2(6) . . . . ? C20 C21 C22 C25 -180.0(4) . . . . ? C18 C17 C22 C21 -1.9(5) . . . . ? N1 C17 C22 C21 -175.5(3) . . . . ? C18 C17 C22 C25 178.3(3) . . . . ? N1 C17 C22 C25 4.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.150 _refine_diff_density_min -0.931 _refine_diff_density_rms 0.103 # Attachment '- ic15048-1.cif' data_ic15048 _database_code_depnum_ccdc_archive 'CCDC 848940' #TrackingRef '- ic15048-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H6 Br N2 O4 Re' _chemical_formula_weight 448.25 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2595(2) _cell_length_b 10.7162(3) _cell_length_c 13.2087(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.183(3) _cell_angle_gamma 90.00 _cell_volume 1157.20(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6824 _cell_measurement_theta_min 3.1278 _cell_measurement_theta_max 29.8311 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 13.949 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.16364 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13362 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2650 _reflns_number_gt 2270 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0371P)^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 SHELXL _refine_ls_extinction_coef 0.0062(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2650 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.29813(2) 0.860469(15) 0.182227(12) 0.03994(10) Uani 1 1 d . . . Br1 Br 0.20216(5) 1.01476(5) 0.31805(3) 0.05083(14) Uani 1 1 d . . . O1 O -0.0520(6) 0.8561(5) 0.0620(4) 0.1032(19) Uani 1 1 d . . . O2 O 0.2241(6) 0.6403(4) 0.3241(3) 0.0817(15) Uani 1 1 d . . . O3 O 0.4176(6) 0.6848(4) 0.0268(3) 0.0700(11) Uani 1 1 d . . . O4 O 0.3964(5) 1.0911(4) 0.0597(3) 0.0772(11) Uani 1 1 d . . . N1 N 0.6712(5) 0.8045(4) 0.2518(3) 0.0647(12) Uani 1 1 d . . . H1A H 0.6690 0.7533 0.2014 0.078 Uiso 1 1 calc R . . N2 N 0.5888(5) 0.9365(4) 0.3501(3) 0.0557(10) Uani 1 1 d . . . H2A H 0.5262 0.9904 0.3733 0.067 Uiso 1 1 calc R . . C1 C 0.0750(7) 0.8583(4) 0.1072(5) 0.0595(14) Uani 1 1 d . . . C2 C 0.2504(6) 0.7195(5) 0.2726(4) 0.0531(12) Uani 1 1 d . . . C3 C 0.3716(6) 0.7505(4) 0.0856(4) 0.0499(11) Uani 1 1 d . . . C4 C 0.3577(6) 1.0076(4) 0.1031(4) 0.0514(11) Uani 1 1 d . . . C5 C 0.5403(6) 0.8672(3) 0.2686(4) 0.0387(10) Uani 1 1 d . . . C6 C 0.8188(6) 0.8267(5) 0.3228(4) 0.0620(13) Uani 1 1 d . . . H6A H 0.9032 0.8652 0.2892 0.074 Uiso 1 1 calc R . . H6B H 0.8608 0.7501 0.3559 0.074 Uiso 1 1 calc R . . C7 C 0.7564(6) 0.9147(6) 0.3974(4) 0.0656(13) Uani 1 1 d . . . H7A H 0.7601 0.8766 0.4643 0.079 Uiso 1 1 calc R . . H7B H 0.8189 0.9916 0.4040 0.079 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 Re1 0.03910(15) 0.04298(14) 0.03722(13) -0.00098(6) 0.00369(9) -0.00356(6) Br1 0.0470(3) 0.0510(3) 0.0570(3) -0.00668(19) 0.0159(2) -0.00188(18) O1 0.056(3) 0.144(5) 0.098(4) -0.001(3) -0.028(3) -0.007(3) O2 0.092(4) 0.074(3) 0.079(3) 0.0211(19) 0.014(3) -0.023(2) O3 0.099(3) 0.059(2) 0.056(2) -0.0123(19) 0.021(2) 0.001(2) O4 0.091(3) 0.064(2) 0.081(3) 0.023(2) 0.029(2) 0.001(2) N1 0.044(2) 0.080(3) 0.069(3) -0.030(2) 0.005(2) 0.006(2) N2 0.046(2) 0.071(3) 0.050(2) -0.020(2) 0.0045(18) 0.0058(19) C1 0.045(3) 0.071(4) 0.060(3) 0.003(2) 0.001(3) -0.003(2) C2 0.054(3) 0.058(3) 0.047(3) -0.004(2) 0.002(2) -0.015(2) C3 0.061(3) 0.048(2) 0.041(2) 0.002(2) 0.006(2) -0.008(2) C4 0.053(3) 0.054(3) 0.050(3) 0.001(2) 0.014(2) 0.005(2) C5 0.038(2) 0.039(2) 0.041(2) 0.0022(16) 0.011(2) -0.0075(16) C6 0.040(3) 0.070(3) 0.074(4) -0.010(3) 0.002(3) 0.000(2) C7 0.047(3) 0.089(4) 0.057(3) -0.013(3) -0.003(2) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C3 1.899(5) . ? Re1 C1 1.964(6) . ? Re1 C4 1.991(5) . ? Re1 C2 1.998(5) . ? Re1 C5 2.158(5) . ? Re1 Br1 2.6430(5) . ? O1 C1 1.131(7) . ? O2 C2 1.128(6) . ? O3 C3 1.153(6) . ? O4 C4 1.134(6) . ? N1 C5 1.319(6) . ? N1 C6 1.448(7) . ? N1 H1A 0.8600 . ? N2 C5 1.322(5) . ? N2 C7 1.455(6) . ? N2 H2A 0.8600 . ? C6 C7 1.507(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 Re1 C1 91.1(2) . . ? C3 Re1 C4 90.68(18) . . ? C1 Re1 C4 91.7(2) . . ? C3 Re1 C2 92.4(2) . . ? C1 Re1 C2 92.4(2) . . ? C4 Re1 C2 174.88(19) . . ? C3 Re1 C5 90.88(19) . . ? C1 Re1 C5 177.97(19) . . ? C4 Re1 C5 88.35(17) . . ? C2 Re1 C5 87.50(18) . . ? C3 Re1 Br1 178.83(15) . . ? C1 Re1 Br1 89.97(17) . . ? C4 Re1 Br1 88.93(13) . . ? C2 Re1 Br1 87.92(14) . . ? C5 Re1 Br1 88.00(11) . . ? C5 N1 C6 116.3(4) . . ? C5 N1 H1A 121.9 . . ? C6 N1 H1A 121.9 . . ? C5 N2 C7 114.8(4) . . ? C5 N2 H2A 122.6 . . ? C7 N2 H2A 122.6 . . ? O1 C1 Re1 178.4(6) . . ? O2 C2 Re1 179.6(5) . . ? O3 C3 Re1 179.2(4) . . ? O4 C4 Re1 177.9(5) . . ? N1 C5 N2 105.2(4) . . ? N1 C5 Re1 127.9(3) . . ? N2 C5 Re1 126.9(3) . . ? N1 C6 C7 101.0(4) . . ? N1 C6 H6A 111.6 . . ? C7 C6 H6A 111.6 . . ? N1 C6 H6B 111.6 . . ? C7 C6 H6B 111.6 . . ? H6A C6 H6B 109.4 . . ? N2 C7 C6 102.3(4) . . ? N2 C7 H7A 111.3 . . ? C6 C7 H7A 111.3 . . ? N2 C7 H7B 111.3 . . ? C6 C7 H7B 111.3 . . ? H7A C7 H7B 109.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 Re1 C1 O1 -21(18) . . . . ? C4 Re1 C1 O1 70(18) . . . . ? C2 Re1 C1 O1 -113(18) . . . . ? C5 Re1 C1 O1 160(15) . . . . ? Br1 Re1 C1 O1 159(18) . . . . ? C3 Re1 C2 O2 126(74) . . . . ? C1 Re1 C2 O2 -143(74) . . . . ? C4 Re1 C2 O2 -1(75) . . . . ? C5 Re1 C2 O2 35(74) . . . . ? Br1 Re1 C2 O2 -53(74) . . . . ? C1 Re1 C3 O3 127(36) . . . . ? C4 Re1 C3 O3 35(36) . . . . ? C2 Re1 C3 O3 -141(36) . . . . ? C5 Re1 C3 O3 -53(36) . . . . ? Br1 Re1 C3 O3 -36(41) . . . . ? C3 Re1 C4 O4 -87(12) . . . . ? C1 Re1 C4 O4 -178(100) . . . . ? C2 Re1 C4 O4 40(13) . . . . ? C5 Re1 C4 O4 4(12) . . . . ? Br1 Re1 C4 O4 92(12) . . . . ? C6 N1 C5 N2 0.7(6) . . . . ? C6 N1 C5 Re1 -179.6(4) . . . . ? C7 N2 C5 N1 -4.9(6) . . . . ? C7 N2 C5 Re1 175.4(3) . . . . ? C3 Re1 C5 N1 -3.9(4) . . . . ? C1 Re1 C5 N1 175(5) . . . . ? C4 Re1 C5 N1 -94.6(4) . . . . ? C2 Re1 C5 N1 88.4(4) . . . . ? Br1 Re1 C5 N1 176.5(4) . . . . ? C3 Re1 C5 N2 175.7(4) . . . . ? C1 Re1 C5 N2 -5(5) . . . . ? C4 Re1 C5 N2 85.0(4) . . . . ? C2 Re1 C5 N2 -92.0(4) . . . . ? Br1 Re1 C5 N2 -4.0(4) . . . . ? C5 N1 C6 C7 3.3(6) . . . . ? C5 N2 C7 C6 6.8(6) . . . . ? N1 C6 C7 N2 -5.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.005 _refine_diff_density_min -0.983 _refine_diff_density_rms 0.126 # Attachment 'ic15074-revised-3.cif' data_ic15074 _database_code_depnum_ccdc_archive 'CCDC 848941' #TrackingRef 'ic15074-revised-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 Br N2 O4 Re' _chemical_formula_weight 682.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.6499(4) _cell_length_b 17.6537(4) _cell_length_c 8.6473(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.798(2) _cell_angle_gamma 90.00 _cell_volume 2646.67(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8960 _cell_measurement_theta_min 3.0207 _cell_measurement_theta_max 28.7324 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 6.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.25547 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'multiwire proportional' _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 27091 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5920 _reflns_number_gt 5064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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_number_reflns 5920 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _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 Re1 Re 0.281264(10) 0.479335(10) 0.507441(19) 0.04411(11) Uani 1 1 d . . . Br1 Br 0.19630(4) 0.58226(4) 0.61255(7) 0.07144(18) Uani 1 1 d . . . O1 O 0.3407(3) 0.4159(4) 0.8417(5) 0.0951(16) Uani 1 1 d . . . O2 O 0.1483(3) 0.3690(3) 0.5388(7) 0.113(2) Uani 1 1 d . . . O3 O 0.3776(4) 0.3623(4) 0.3778(8) 0.132(2) Uani 1 1 d . . . O4 O 0.4202(3) 0.5903(4) 0.6050(5) 0.1064(19) Uani 1 1 d . . . N1 N 0.1803(3) 0.4940(3) 0.1589(5) 0.0555(10) Uani 1 1 d . . . N2 N 0.2718(2) 0.5743(2) 0.1875(4) 0.0514(9) Uani 1 1 d . . . C1 C 0.3173(3) 0.4420(4) 0.7191(6) 0.0681(15) Uani 1 1 d . . . C2 C 0.1934(4) 0.4088(3) 0.5101(7) 0.0643(14) Uani 1 1 d . . . C3 C 0.3430(4) 0.4047(4) 0.4261(7) 0.0748(16) Uani 1 1 d . . . C4 C 0.3688(3) 0.5538(4) 0.5540(7) 0.0673(15) Uani 1 1 d . . . C5 C 0.2403(3) 0.5202(2) 0.2673(6) 0.0425(10) Uani 1 1 d . . . C6 C 0.1771(4) 0.5280(4) 0.0152(8) 0.081(2) Uani 1 1 d . . . H6A H 0.1412 0.5183 -0.0759 0.097 Uiso 1 1 calc R . . C7 C 0.2355(4) 0.5782(4) 0.0304(7) 0.081(2) Uani 1 1 d . . . H7A H 0.2488 0.6089 -0.0477 0.098 Uiso 1 1 calc R . . C8 C 0.1243(3) 0.4366(3) 0.1797(6) 0.0530(11) Uani 1 1 d . . . C9 C 0.0566(3) 0.4564(3) 0.2287(6) 0.0569(12) Uani 1 1 d . . . C10 C 0.0056(3) 0.3998(4) 0.2449(7) 0.0685(15) Uani 1 1 d . . . H10A H -0.0394 0.4119 0.2808 0.082 Uiso 1 1 calc R . . C11 C 0.0190(3) 0.3258(4) 0.2096(9) 0.0774(17) Uani 1 1 d . . . C12 C 0.0848(4) 0.3076(4) 0.1556(9) 0.085(2) Uani 1 1 d . . . H12A H 0.0934 0.2576 0.1296 0.102 Uiso 1 1 calc R . . C13 C 0.1386(3) 0.3623(4) 0.1389(7) 0.0684(15) Uani 1 1 d . . . C14 C 0.0398(4) 0.5376(4) 0.2604(11) 0.087(2) Uani 1 1 d . . . H14A H -0.0092 0.5410 0.2930 0.131 Uiso 1 1 calc R . . H14B H 0.0384 0.5668 0.1662 0.131 Uiso 1 1 calc R . . H14C H 0.0794 0.5569 0.3422 0.131 Uiso 1 1 calc R . . C15 C -0.0394(5) 0.2651(5) 0.2263(13) 0.122(3) Uani 1 1 d . . . H15A H -0.0211 0.2169 0.1969 0.183 Uiso 1 1 calc R . . H15B H -0.0877 0.2768 0.1590 0.183 Uiso 1 1 calc R . . H15C H -0.0464 0.2630 0.3337 0.183 Uiso 1 1 calc R . . C16 C 0.2104(4) 0.3413(6) 0.0737(12) 0.119(3) Uani 1 1 d . . . H16A H 0.2101 0.2879 0.0525 0.178 Uiso 1 1 calc R . . H16B H 0.2557 0.3539 0.1496 0.178 Uiso 1 1 calc R . . H16C H 0.2107 0.3688 -0.0219 0.178 Uiso 1 1 calc R . . C17 C 0.3358(3) 0.6239(3) 0.2439(5) 0.0479(10) Uani 1 1 d . . . C18 C 0.3210(3) 0.6935(3) 0.3040(7) 0.0571(12) Uani 1 1 d . . . C19 C 0.3827(3) 0.7420(3) 0.3506(7) 0.0683(14) Uani 1 1 d . . . H19A H 0.3738 0.7891 0.3919 0.082 Uiso 1 1 calc R . . C20 C 0.4571(3) 0.7225(3) 0.3377(7) 0.0653(14) Uani 1 1 d . . . C21 C 0.4686(3) 0.6541(4) 0.2748(7) 0.0655(14) Uani 1 1 d . . . H21A H 0.5185 0.6411 0.2647 0.079 Uiso 1 1 calc R . . C22 C 0.4100(3) 0.6025(3) 0.2246(6) 0.0568(12) Uani 1 1 d . . . C23 C 0.2411(3) 0.7173(4) 0.3169(10) 0.089(2) Uani 1 1 d . . . H23A H 0.2424 0.7672 0.3611 0.133 Uiso 1 1 calc R . . H23B H 0.2205 0.6824 0.3836 0.133 Uiso 1 1 calc R . . H23D H 0.2090 0.7174 0.2141 0.133 Uiso 1 1 calc R . . C24 C 0.5235(4) 0.7765(5) 0.3862(9) 0.099(2) Uani 1 1 d . . . H24A H 0.5703 0.7533 0.3688 0.148 Uiso 1 1 calc R . . H24D H 0.5281 0.7887 0.4957 0.148 Uiso 1 1 calc R . . H24B H 0.5142 0.8221 0.3248 0.148 Uiso 1 1 calc R . . C25 C 0.4269(5) 0.5272(4) 0.1564(11) 0.093(2) Uani 1 1 d . . . H25D H 0.4809 0.5239 0.1535 0.139 Uiso 1 1 calc R . . H25A H 0.3976 0.5225 0.0515 0.139 Uiso 1 1 calc R . . H25B H 0.4131 0.4870 0.2207 0.139 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 Re1 0.04502(15) 0.04919(15) 0.03853(15) 0.00526(6) 0.00885(9) 0.00355(7) Br1 0.0869(4) 0.0761(4) 0.0568(3) -0.0115(3) 0.0276(3) 0.0124(3) O1 0.097(3) 0.133(5) 0.053(2) 0.034(3) 0.007(2) 0.010(3) O2 0.117(4) 0.107(4) 0.104(4) 0.054(3) -0.011(3) -0.050(3) O3 0.145(5) 0.123(5) 0.131(5) -0.003(4) 0.035(4) 0.083(5) O4 0.088(3) 0.145(5) 0.074(3) 0.010(3) -0.016(2) -0.060(3) N1 0.058(3) 0.061(2) 0.044(2) 0.0024(19) -0.0006(19) -0.017(2) N2 0.053(2) 0.056(2) 0.043(2) 0.0108(17) 0.0021(17) -0.0115(18) C1 0.065(3) 0.095(4) 0.043(3) 0.017(3) 0.006(2) 0.006(3) C2 0.075(3) 0.045(3) 0.068(3) 0.022(2) -0.001(3) -0.013(3) C3 0.088(4) 0.076(4) 0.059(3) 0.008(3) 0.009(3) 0.028(4) C4 0.060(3) 0.090(4) 0.050(3) 0.010(3) 0.006(2) -0.010(3) C5 0.046(2) 0.043(2) 0.039(2) -0.0031(16) 0.0095(19) 0.0018(17) C6 0.077(4) 0.107(5) 0.049(3) 0.018(3) -0.010(3) -0.029(4) C7 0.087(4) 0.094(5) 0.053(3) 0.025(3) -0.016(3) -0.026(4) C8 0.053(3) 0.053(3) 0.052(3) -0.002(2) 0.008(2) -0.010(2) C9 0.048(3) 0.060(3) 0.056(3) -0.003(2) -0.006(2) 0.002(2) C10 0.042(3) 0.086(4) 0.076(4) 0.000(3) 0.007(2) 0.002(3) C11 0.055(3) 0.071(4) 0.106(5) -0.003(3) 0.014(3) -0.020(3) C12 0.072(4) 0.058(3) 0.129(6) -0.025(4) 0.027(4) -0.017(3) C13 0.064(3) 0.066(3) 0.079(4) -0.020(3) 0.023(3) -0.013(3) C14 0.067(4) 0.068(4) 0.116(6) -0.016(4) -0.011(4) 0.021(3) C15 0.093(6) 0.098(6) 0.178(9) -0.002(6) 0.033(6) -0.043(5) C16 0.090(5) 0.123(7) 0.160(8) -0.072(6) 0.067(5) -0.018(5) C17 0.053(2) 0.049(2) 0.042(2) 0.0064(18) 0.0110(19) -0.009(2) C18 0.056(3) 0.045(2) 0.074(3) 0.012(2) 0.023(2) 0.001(2) C19 0.076(4) 0.049(3) 0.084(4) -0.001(3) 0.024(3) -0.013(3) C20 0.063(3) 0.068(3) 0.066(3) 0.004(3) 0.015(3) -0.022(3) C21 0.049(3) 0.083(4) 0.068(3) 0.001(3) 0.019(2) -0.004(3) C22 0.055(3) 0.064(3) 0.055(3) 0.000(2) 0.021(2) 0.002(2) C23 0.067(4) 0.054(3) 0.155(7) 0.026(4) 0.046(4) 0.016(3) C24 0.086(4) 0.111(6) 0.094(5) 0.010(4) 0.004(4) -0.053(4) C25 0.087(5) 0.093(5) 0.108(6) -0.037(4) 0.044(5) 0.001(4) _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 Re1 C3 1.925(7) . ? Re1 C1 1.937(5) . ? Re1 C2 1.992(6) . ? Re1 C4 2.010(6) . ? Re1 C5 2.190(5) . ? Re1 Br1 2.6243(6) . ? O1 C1 1.159(6) . ? O2 C2 1.125(7) . ? O3 C3 1.097(8) . ? O4 C4 1.133(7) . ? N1 C5 1.357(6) . ? N1 C6 1.372(8) . ? N1 C8 1.450(7) . ? N2 C5 1.357(6) . ? N2 C7 1.391(7) . ? N2 C17 1.440(6) . ? C6 C7 1.346(9) . ? C8 C9 1.386(8) . ? C8 C13 1.393(8) . ? C9 C10 1.368(9) . ? C9 C14 1.500(8) . ? C10 C11 1.373(10) . ? C11 C12 1.368(9) . ? C11 C15 1.512(9) . ? C12 C13 1.381(8) . ? C13 C16 1.526(8) . ? C17 C18 1.379(7) . ? C17 C22 1.402(7) . ? C18 C19 1.384(8) . ? C18 C23 1.497(7) . ? C19 C20 1.382(8) . ? C20 C21 1.356(9) . ? C20 C24 1.508(8) . ? C21 C22 1.385(8) . ? C22 C25 1.508(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 Re1 C1 90.2(3) . . ? C3 Re1 C2 94.1(3) . . ? C1 Re1 C2 84.0(3) . . ? C3 Re1 C4 93.1(3) . . ? C1 Re1 C4 85.9(3) . . ? C2 Re1 C4 167.6(2) . . ? C3 Re1 C5 89.3(2) . . ? C1 Re1 C5 179.3(2) . . ? C2 Re1 C5 95.59(19) . . ? C4 Re1 C5 94.6(2) . . ? C3 Re1 Br1 178.83(18) . . ? C1 Re1 Br1 90.9(2) . . ? C2 Re1 Br1 86.1(2) . . ? C4 Re1 Br1 86.9(2) . . ? C5 Re1 Br1 89.52(12) . . ? C5 N1 C6 111.7(5) . . ? C5 N1 C8 127.9(4) . . ? C6 N1 C8 120.4(5) . . ? C5 N2 C7 111.9(4) . . ? C5 N2 C17 128.8(4) . . ? C7 N2 C17 119.3(4) . . ? O1 C1 Re1 175.9(6) . . ? O2 C2 Re1 168.1(5) . . ? O3 C3 Re1 179.1(7) . . ? O4 C4 Re1 168.3(5) . . ? N2 C5 N1 103.3(4) . . ? N2 C5 Re1 128.3(3) . . ? N1 C5 Re1 128.2(3) . . ? C7 C6 N1 107.4(5) . . ? C6 C7 N2 105.5(5) . . ? C9 C8 C13 121.5(5) . . ? C9 C8 N1 120.6(5) . . ? C13 C8 N1 117.8(5) . . ? C10 C9 C8 117.9(5) . . ? C10 C9 C14 121.5(6) . . ? C8 C9 C14 120.5(6) . . ? C9 C10 C11 121.9(6) . . ? C12 C11 C10 119.4(6) . . ? C12 C11 C15 120.3(7) . . ? C10 C11 C15 120.3(7) . . ? C11 C12 C13 121.1(6) . . ? C12 C13 C8 118.1(5) . . ? C12 C13 C16 120.3(6) . . ? C8 C13 C16 121.7(6) . . ? C18 C17 C22 122.1(4) . . ? C18 C17 N2 118.5(4) . . ? C22 C17 N2 119.1(4) . . ? C17 C18 C19 117.9(5) . . ? C17 C18 C23 121.7(5) . . ? C19 C18 C23 120.4(5) . . ? C20 C19 C18 122.0(5) . . ? C21 C20 C19 118.1(5) . . ? C21 C20 C24 120.5(6) . . ? C19 C20 C24 121.4(6) . . ? C20 C21 C22 123.5(5) . . ? C21 C22 C17 116.4(5) . . ? C21 C22 C25 120.7(5) . . ? C17 C22 C25 122.8(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 C3 Re1 C1 O1 -12(8) . . . . ? C2 Re1 C1 O1 82(8) . . . . ? C4 Re1 C1 O1 -105(8) . . . . ? C5 Re1 C1 O1 34(25) . . . . ? Br1 Re1 C1 O1 168(8) . . . . ? C3 Re1 C2 O2 106(3) . . . . ? C1 Re1 C2 O2 16(3) . . . . ? C4 Re1 C2 O2 -20(4) . . . . ? C5 Re1 C2 O2 -165(3) . . . . ? Br1 Re1 C2 O2 -75(3) . . . . ? C1 Re1 C3 O3 160(50) . . . . ? C2 Re1 C3 O3 76(50) . . . . ? C4 Re1 C3 O3 -114(50) . . . . ? C5 Re1 C3 O3 -19(50) . . . . ? Br1 Re1 C3 O3 -24(59) . . . . ? C3 Re1 C4 O4 -93(3) . . . . ? C1 Re1 C4 O4 -3(3) . . . . ? C2 Re1 C4 O4 32(4) . . . . ? C5 Re1 C4 O4 177(3) . . . . ? Br1 Re1 C4 O4 88(3) . . . . ? C7 N2 C5 N1 -3.9(6) . . . . ? C17 N2 C5 N1 177.5(5) . . . . ? C7 N2 C5 Re1 172.1(5) . . . . ? C17 N2 C5 Re1 -6.5(7) . . . . ? C6 N1 C5 N2 2.8(7) . . . . ? C8 N1 C5 N2 -178.1(5) . . . . ? C6 N1 C5 Re1 -173.2(5) . . . . ? C8 N1 C5 Re1 5.9(8) . . . . ? C3 Re1 C5 N2 -89.2(5) . . . . ? C1 Re1 C5 N2 -135(19) . . . . ? C2 Re1 C5 N2 176.7(4) . . . . ? C4 Re1 C5 N2 3.9(5) . . . . ? Br1 Re1 C5 N2 90.7(4) . . . . ? C3 Re1 C5 N1 85.8(5) . . . . ? C1 Re1 C5 N1 40(19) . . . . ? C2 Re1 C5 N1 -8.2(5) . . . . ? C4 Re1 C5 N1 178.9(5) . . . . ? Br1 Re1 C5 N1 -94.3(4) . . . . ? C5 N1 C6 C7 -0.8(9) . . . . ? C8 N1 C6 C7 -179.9(6) . . . . ? N1 C6 C7 N2 -1.6(9) . . . . ? C5 N2 C7 C6 3.5(8) . . . . ? C17 N2 C7 C6 -177.7(6) . . . . ? C5 N1 C8 C9 89.7(7) . . . . ? C6 N1 C8 C9 -91.4(7) . . . . ? C5 N1 C8 C13 -94.5(7) . . . . ? C6 N1 C8 C13 84.5(8) . . . . ? C13 C8 C9 C10 3.7(8) . . . . ? N1 C8 C9 C10 179.4(5) . . . . ? C13 C8 C9 C14 -175.4(6) . . . . ? N1 C8 C9 C14 0.3(8) . . . . ? C8 C9 C10 C11 -2.0(9) . . . . ? C14 C9 C10 C11 177.1(6) . . . . ? C9 C10 C11 C12 -0.5(11) . . . . ? C9 C10 C11 C15 -178.9(7) . . . . ? C10 C11 C12 C13 1.3(11) . . . . ? C15 C11 C12 C13 179.8(8) . . . . ? C11 C12 C13 C8 0.4(11) . . . . ? C11 C12 C13 C16 -178.1(8) . . . . ? C9 C8 C13 C12 -2.9(9) . . . . ? N1 C8 C13 C12 -178.8(6) . . . . ? C9 C8 C13 C16 175.5(6) . . . . ? N1 C8 C13 C16 -0.3(9) . . . . ? C5 N2 C17 C18 -91.0(6) . . . . ? C7 N2 C17 C18 90.4(6) . . . . ? C5 N2 C17 C22 94.0(6) . . . . ? C7 N2 C17 C22 -84.6(7) . . . . ? C22 C17 C18 C19 -2.1(7) . . . . ? N2 C17 C18 C19 -176.9(5) . . . . ? C22 C17 C18 C23 177.0(5) . . . . ? N2 C17 C18 C23 2.2(7) . . . . ? C17 C18 C19 C20 0.3(8) . . . . ? C23 C18 C19 C20 -178.8(6) . . . . ? C18 C19 C20 C21 1.1(9) . . . . ? C18 C19 C20 C24 178.8(6) . . . . ? C19 C20 C21 C22 -0.8(9) . . . . ? C24 C20 C21 C22 -178.5(6) . . . . ? C20 C21 C22 C17 -0.9(8) . . . . ? C20 C21 C22 C25 -179.7(7) . . . . ? C18 C17 C22 C21 2.4(7) . . . . ? N2 C17 C22 C21 177.2(5) . . . . ? C18 C17 C22 C25 -178.9(6) . . . . ? N2 C17 C22 C25 -4.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 1.812 _refine_diff_density_min -1.696 _refine_diff_density_rms 0.100