Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Isabel Santos' _publ_contact_author_address ; Quimica Instituto Tecnologico e Nuclear Estrada Nacional, 10, Apartado 21 Sacavem Portugal 2686-953 PORTUGAL ; _publ_contact_author_email ISANTOS@ITN.PT _publ_section_title ; Rhenium and Technetium Tricarbonyl Complexes Anchored by Pyrazole-Based Tripods: Novel Lead Structures for the Design of Myocardial Imaging Agents ; loop_ _publ_author_name 'Isabel Santos' 'Susana Cunha' 'Lurdes Gano' 'Leonor Maria' 'Antonio Paulo' 'Margherita Videira' data_rebr _database_code_depnum_ccdc_archive 'CCDC 643757' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (Re(CO)3(NH2CH2CH(pz)2))Br _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N5 O3 Re, C H4 O, Br' _chemical_formula_sum 'C12 H15 Br N5 O4 Re' _chemical_formula_weight 559.40 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 P21/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 12.5900(2) _cell_length_b 10.0842(2) _cell_length_c 14.5569(2) _cell_angle_alpha 90.0000(10) _cell_angle_beta 110.3190(10) _cell_angle_gamma 90.0000(10) _cell_volume 1733.14(5) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 9.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1178 _exptl_absorpt_correction_T_max 0.2566 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-AXS APEX- CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15143 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3529 _reflns_number_gt 2995 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT, (Bruker, 2004)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3(Farrugia,1997) _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0444P)^2^+0.1234P] 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 3529 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0938 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.007 _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 Br1 Br 0.38348(4) -0.06112(5) 0.29736(4) 0.02394(14) Uani 1 1 d . . . Re1 Re 0.719327(14) 0.001742(14) 0.256272(13) 0.01102(10) Uani 1 1 d . . . C1 C 0.5909(4) -0.0674(5) 0.1518(4) 0.0187(10) Uani 1 1 d . . . C2 C 0.8182(4) -0.1230(5) 0.2257(3) 0.0174(10) Uani 1 1 d . . . C3 C 0.7446(4) 0.1200(5) 0.1619(4) 0.0180(10) Uani 1 1 d . . . O1 O 0.5135(3) -0.1048(4) 0.0886(3) 0.0293(9) Uani 1 1 d . . . O2 O 0.8762(3) -0.2000(4) 0.2089(3) 0.0309(9) Uani 1 1 d . . . O3 O 0.7633(3) 0.1846(4) 0.1038(3) 0.0279(8) Uani 1 1 d . . . N1 N 0.6973(3) -0.1261(4) 0.3689(3) 0.0121(7) Uani 1 1 d . . . N2 N 0.7055(3) -0.0773(4) 0.4582(3) 0.0168(9) Uani 1 1 d . . . N3 N 0.8499(3) 0.0918(4) 0.3801(3) 0.0142(8) Uani 1 1 d . . . N4 N 0.8386(3) 0.0960(4) 0.4708(3) 0.0143(8) Uani 1 1 d . . . N5 N 0.6079(3) 0.1306(4) 0.3088(3) 0.0151(8) Uani 1 1 d . . . H5A H 0.6044 0.2122 0.2797 0.018 Uiso 1 1 calc R . . H5B H 0.5362 0.0951 0.2852 0.018 Uiso 1 1 calc R . . C4 C 0.6772(4) -0.2555(4) 0.3722(4) 0.0170(9) Uani 1 1 d . . . H4 H 0.6693 -0.3164 0.3204 0.020 Uiso 1 1 calc R . . C5 C 0.6695(4) -0.2888(5) 0.4631(4) 0.0267(12) Uani 1 1 d . . . H5 H 0.6547 -0.3738 0.4840 0.032 Uiso 1 1 calc R . . C6 C 0.6879(4) -0.1726(5) 0.5157(4) 0.0250(11) Uani 1 1 d . . . H6 H 0.6880 -0.1618 0.5805 0.030 Uiso 1 1 calc R . . C7 C 0.7291(4) 0.0629(5) 0.4796(4) 0.0148(10) Uani 1 1 d . . . H7 H 0.7358 0.0778 0.5493 0.018 Uiso 1 1 calc R . . C8 C 0.6361(4) 0.1538(5) 0.4161(3) 0.0159(9) Uani 1 1 d . . . H8B H 0.5671 0.1404 0.4328 0.019 Uiso 1 1 calc R . . H8A H 0.6604 0.2471 0.4313 0.019 Uiso 1 1 calc R . . C9 C 0.9313(4) 0.1499(5) 0.5384(4) 0.0198(10) Uani 1 1 d . . . H9 H 0.9431 0.1647 0.6057 0.024 Uiso 1 1 calc R . . C10 C 1.0055(4) 0.1793(6) 0.4903(4) 0.0218(12) Uani 1 1 d . . . H10 H 1.0788 0.2171 0.5182 0.026 Uiso 1 1 calc R . . C11 C 0.9515(4) 0.1423(5) 0.3921(4) 0.0188(10) Uani 1 1 d . . . H11 H 0.9828 0.1520 0.3417 0.023 Uiso 1 1 calc R . . O4 O 0.1113(4) -0.0494(7) 0.2574(4) 0.0561(14) Uani 1 1 d . . . H4A H 0.1818 -0.0516 0.2713 0.084 Uiso 1 1 calc R . . C12 C 0.0595(7) 0.0101(6) 0.1632(6) 0.0431(18) Uani 1 1 d . . . H12A H 0.0244 0.0944 0.1703 0.065 Uiso 1 1 calc R . . H12B H 0.0015 -0.0496 0.1211 0.065 Uiso 1 1 calc R . . H12C H 0.1172 0.0264 0.1334 0.065 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 Br1 0.0224(2) 0.0184(3) 0.0335(3) -0.0016(2) 0.0128(2) -0.0033(2) Re1 0.01235(14) 0.01006(15) 0.01057(16) 0.00037(6) 0.00388(11) -0.00124(5) C1 0.024(2) 0.016(2) 0.020(3) -0.001(2) 0.013(2) -0.0059(19) C2 0.020(2) 0.019(2) 0.011(2) -0.002(2) 0.0028(19) -0.0041(19) C3 0.018(2) 0.013(2) 0.019(3) -0.001(2) 0.002(2) -0.0016(18) O1 0.0262(19) 0.039(2) 0.020(2) -0.0085(17) 0.0054(16) -0.0137(16) O2 0.0288(18) 0.029(2) 0.037(2) -0.0054(18) 0.0146(17) 0.0100(16) O3 0.037(2) 0.026(2) 0.023(2) 0.0087(17) 0.0134(17) -0.0037(16) N1 0.0161(17) 0.0107(18) 0.0105(19) 0.0009(15) 0.0060(15) 0.0014(14) N2 0.0181(19) 0.015(2) 0.017(2) -0.0007(17) 0.0068(16) -0.0009(16) N3 0.0148(17) 0.014(2) 0.014(2) -0.0003(16) 0.0053(15) -0.0022(14) N4 0.0130(17) 0.016(2) 0.012(2) -0.0035(16) 0.0019(15) 0.0008(14) N5 0.0157(17) 0.0122(19) 0.015(2) -0.0008(16) 0.0020(15) -0.0011(15) C4 0.021(2) 0.012(2) 0.018(3) -0.0015(19) 0.0076(19) -0.0049(18) C5 0.039(3) 0.017(3) 0.028(3) 0.006(2) 0.018(2) -0.001(2) C6 0.037(3) 0.022(3) 0.021(3) 0.007(2) 0.017(2) 0.002(2) C7 0.014(2) 0.014(2) 0.015(2) -0.003(2) 0.0045(18) -0.0012(18) C8 0.016(2) 0.015(2) 0.015(2) -0.0014(19) 0.0037(18) 0.0024(17) C9 0.017(2) 0.014(2) 0.023(3) -0.007(2) -0.001(2) 0.0040(18) C10 0.016(2) 0.017(3) 0.030(3) -0.006(2) 0.004(2) -0.0016(17) C11 0.017(2) 0.016(2) 0.022(3) -0.001(2) 0.0045(19) -0.0015(18) O4 0.028(2) 0.094(4) 0.047(3) 0.033(3) 0.015(2) 0.006(3) C12 0.048(4) 0.042(4) 0.040(5) 0.008(3) 0.016(4) -0.005(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 C1 1.925(5) . ? Re1 C3 1.927(5) . ? Re1 C2 1.927(5) . ? Re1 N3 2.172(4) . ? Re1 N1 2.177(4) . ? Re1 N5 2.233(4) . ? C1 O1 1.147(6) . ? C2 O2 1.149(6) . ? C3 O3 1.156(6) . ? N1 C4 1.334(6) . ? N1 N2 1.360(5) . ? N2 C6 1.342(6) . ? N2 C7 1.455(7) . ? N3 C11 1.331(6) . ? N3 N4 1.377(5) . ? N4 C9 1.352(6) . ? N4 C7 1.467(6) . ? N5 C8 1.495(6) . ? C4 C5 1.401(7) . ? C5 C6 1.375(7) . ? C7 C8 1.521(6) . ? C9 C10 1.379(7) . ? C10 C11 1.404(7) . ? O4 C12 1.431(9) . ? 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 87.8(2) . . ? C1 Re1 C2 90.8(2) . . ? C3 Re1 C2 87.7(2) . . ? C1 Re1 N3 173.24(16) . . ? C3 Re1 N3 93.91(17) . . ? C2 Re1 N3 95.79(17) . . ? C1 Re1 N1 95.09(17) . . ? C3 Re1 N1 177.02(16) . . ? C2 Re1 N1 92.78(17) . . ? N3 Re1 N1 83.11(14) . . ? C1 Re1 N5 91.51(17) . . ? C3 Re1 N5 99.37(17) . . ? C2 Re1 N5 172.64(16) . . ? N3 Re1 N5 81.77(13) . . ? N1 Re1 N5 80.05(14) . . ? O1 C1 Re1 177.9(4) . . ? O2 C2 Re1 178.1(4) . . ? O3 C3 Re1 175.8(4) . . ? C4 N1 N2 105.8(4) . . ? C4 N1 Re1 133.0(3) . . ? N2 N1 Re1 121.2(3) . . ? C6 N2 N1 111.3(4) . . ? C6 N2 C7 128.9(4) . . ? N1 N2 C7 119.9(4) . . ? C11 N3 N4 106.0(4) . . ? C11 N3 Re1 133.2(3) . . ? N4 N3 Re1 120.6(3) . . ? C9 N4 N3 111.1(4) . . ? C9 N4 C7 128.9(4) . . ? N3 N4 C7 119.3(4) . . ? C8 N5 Re1 120.0(3) . . ? N1 C4 C5 110.2(4) . . ? C6 C5 C4 105.6(4) . . ? N2 C6 C5 107.2(4) . . ? N2 C7 N4 109.3(3) . . ? N2 C7 C8 113.5(4) . . ? N4 C7 C8 111.0(4) . . ? N5 C8 C7 113.2(4) . . ? N4 C9 C10 106.4(4) . . ? C9 C10 C11 106.7(4) . . ? N3 C11 C10 109.8(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.635 _refine_diff_density_min -2.585 _refine_diff_density_rms 0.247 data_cad4b _database_code_depnum_ccdc_archive 'CCDC 646540' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Re(CO)3{MeOCH2C(pz)3}]Br (2)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 Br Cl0 N6 O4 Re' _chemical_formula_weight 608.43 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b n b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x-1/2, -y, z-1/2' _cell_length_a 11.376(5) _cell_length_b 20.119(5) _cell_length_c 23.566(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 5394(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 6.011 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.2774 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'Psi-scan; North' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count 300 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% ? _diffrn_reflns_number 9451 _diffrn_reflns_av_R_equivalents 0.1621 _diffrn_reflns_av_sigmaI/netI 0.2110 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4734 _reflns_number_gt 1823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Software (Enraf-Nonius,1994) ' _computing_cell_refinement 'CAD4 Software (Enraf-Nonius,1994) ' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3(Farrugia,1997) _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.1624P)^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 4734 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2386 _refine_ls_R_factor_gt 0.0960 _refine_ls_wR_factor_ref 0.2973 _refine_ls_wR_factor_gt 0.2431 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_restrained_S_all 0.874 _refine_ls_shift/su_max 2.374 _refine_ls_shift/su_mean 0.103 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 0.75679(9) 0.03263(5) 0.11003(4) 0.0422(4) Uani 1 1 d . . . Br1 Br 0.5254(3) 0.21580(16) 0.04366(14) 0.0655(9) Uani 1 1 d . . . N1 N 0.6867(16) 0.0196(11) 0.0248(7) 0.036(5) Uani 1 1 d . . . N3 N 0.6977(19) -0.1125(12) 0.0756(11) 0.055(7) Uani 1 1 d . . . C2 C 0.820(3) 0.1183(13) 0.0938(11) 0.044(7) Uani 1 1 d . . . N6 N 0.9014(16) -0.0189(10) 0.0725(9) 0.041(5) Uani 1 1 d . . . N4 N 0.6926(19) -0.0662(11) 0.1207(8) 0.042(5) Uani 1 1 d . . . C3 C 0.618(3) 0.0696(18) 0.1398(14) 0.080(11) Uani 1 1 d . . . O2 O 0.855(2) 0.1689(10) 0.0832(11) 0.092(8) Uani 1 1 d . . . C13 C 0.767(2) -0.0929(13) 0.0255(8) 0.042(7) Uani 1 1 d . . . C1 C 0.824(3) 0.0346(18) 0.1841(11) 0.069(10) Uani 1 1 d . . . C9 C 0.627(2) -0.0974(18) 0.1611(10) 0.060(9) Uani 1 1 d . . . H9 H 0.6052 -0.0790 0.1958 0.072 Uiso 1 1 calc R . . O1 O 0.870(2) 0.0393(15) 0.2232(11) 0.111(10) Uani 1 1 d . . . N5 N 0.8892(18) -0.0779(11) 0.0421(8) 0.043(5) Uani 1 1 d . . . C14 C 0.7788(19) -0.1612(15) -0.0132(14) 0.059(9) Uani 1 1 d . . . H14A H 0.8251 -0.1947 0.0063 0.071 Uiso 1 1 calc R . . H14B H 0.7021 -0.1796 -0.0221 0.071 Uiso 1 1 calc R . . O3 O 0.5294(19) 0.0869(12) 0.1578(8) 0.080(7) Uani 1 1 d . . . N2 N 0.706(2) -0.0408(10) -0.0014(8) 0.044(6) Uani 1 1 d . . . O4 O 0.8352(18) -0.1395(12) -0.0618(9) 0.072(7) Uani 1 1 d . . . C7 C 0.648(3) -0.1707(15) 0.0893(15) 0.064(9) Uani 1 1 d . . . H7 H 0.6475 -0.2095 0.0679 0.077 Uiso 1 1 calc R . . C4 C 0.628(2) 0.0523(15) -0.0166(16) 0.070(11) Uani 1 1 d . . . H4 H 0.6094 0.0973 -0.0141 0.084 Uiso 1 1 calc R . . C5 C 0.599(2) 0.0163(18) -0.0597(9) 0.057(10) Uani 1 1 d . . . H5 H 0.5496 0.0286 -0.0894 0.068 Uiso 1 1 calc R . . C8 C 0.596(3) -0.1605(13) 0.1429(16) 0.071(10) Uani 1 1 d . . . H8 H 0.5496 -0.1908 0.1625 0.085 Uiso 1 1 calc R . . C6 C 0.653(2) -0.0412(14) -0.0536(9) 0.044(7) Uani 1 1 d . . . H6 H 0.6545 -0.0758 -0.0799 0.053 Uiso 1 1 calc R . . C11 C 1.071(2) -0.0705(17) 0.0521(13) 0.066(10) Uani 1 1 d . . . H11 H 1.1522 -0.0763 0.0489 0.079 Uiso 1 1 calc R . . C15 C 0.837(3) -0.196(2) -0.0955(18) 0.104(14) Uani 1 1 d . . . C10 C 0.989(2) -0.1114(14) 0.0318(9) 0.042(7) Uani 1 1 d . . . H10 H 0.9978 -0.1528 0.0147 0.050 Uiso 1 1 calc R . . C12 C 1.014(2) -0.0170(13) 0.0794(11) 0.049(7) Uani 1 1 d . . . H12 H 1.0524 0.0159 0.0999 0.059 Uiso 1 1 calc R . . O5 O 0.9236(15) -0.1538(9) 0.1865(6) 0.052(5) Uani 1 1 d . . . C21 C 1.117(3) -0.2395(19) 0.2181(14) 0.080(10) Uiso 1 1 d . . . C20 C 0.848(3) -0.2727(16) 0.2227(13) 0.063(8) Uiso 1 1 d . . . O6 O 1.054(4) -0.275(2) 0.2345(16) 0.08(2) Uiso 0.67(7) 1 d P . . 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 0.0469(6) 0.0351(5) 0.0445(5) -0.0038(5) -0.0010(6) -0.0036(7) Br1 0.068(2) 0.0472(17) 0.081(2) -0.0038(17) -0.0054(17) -0.0033(18) N1 0.025(10) 0.053(16) 0.031(11) 0.000(10) 0.001(8) -0.004(11) N3 0.047(13) 0.043(16) 0.076(18) 0.003(13) -0.024(12) -0.010(12) C2 0.066(19) 0.019(15) 0.046(16) -0.011(11) 0.009(13) 0.001(14) N6 0.029(11) 0.030(13) 0.063(14) 0.004(10) -0.015(10) 0.012(10) N4 0.051(12) 0.034(12) 0.041(12) -0.003(10) -0.032(10) -0.011(11) C3 0.06(2) 0.07(3) 0.11(3) -0.04(2) 0.052(19) 0.00(2) O2 0.10(2) 0.022(12) 0.15(2) 0.011(13) 0.014(16) -0.009(13) C13 0.057(17) 0.049(16) 0.020(11) -0.007(10) -0.010(11) 0.023(16) C1 0.068(19) 0.12(3) 0.021(13) -0.013(17) -0.008(13) -0.02(2) C9 0.046(16) 0.11(3) 0.026(14) 0.025(16) 0.005(12) -0.006(19) O1 0.068(15) 0.18(3) 0.089(17) -0.060(18) -0.023(14) 0.000(18) N5 0.049(13) 0.039(14) 0.041(11) -0.005(11) -0.009(10) -0.013(11) C14 0.015(14) 0.050(18) 0.11(2) -0.038(19) 0.010(13) 0.003(12) O3 0.076(15) 0.095(19) 0.069(14) -0.010(13) -0.002(12) -0.016(15) N2 0.076(15) 0.026(12) 0.031(11) -0.004(9) -0.006(9) -0.008(11) O4 0.066(14) 0.082(18) 0.069(14) -0.034(13) 0.013(11) 0.007(13) C7 0.07(2) 0.038(18) 0.09(3) -0.004(17) -0.003(18) 0.014(17) C4 0.024(14) 0.032(17) 0.15(3) 0.06(2) 0.023(18) 0.009(13) C5 0.041(15) 0.11(3) 0.018(12) 0.005(15) -0.029(11) -0.017(18) C8 0.059(19) 0.008(14) 0.14(3) 0.023(18) 0.000(19) -0.033(15) C6 0.049(15) 0.055(19) 0.029(13) -0.010(13) -0.015(11) 0.038(15) C11 0.022(13) 0.08(3) 0.09(2) 0.03(2) -0.018(14) 0.001(16) C15 0.09(3) 0.10(3) 0.12(4) -0.03(3) 0.01(2) -0.04(3) C10 0.031(14) 0.061(19) 0.033(14) 0.010(12) 0.004(10) 0.019(15) C12 0.065(19) 0.027(16) 0.056(17) 0.001(13) -0.001(15) -0.011(15) O5 0.069(12) 0.064(13) 0.022(8) -0.012(8) -0.018(8) 0.044(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C3 1.88(3) . ? Re1 C1 1.91(3) . ? Re1 C2 1.91(3) . ? Re1 N4 2.13(2) . ? Re1 N6 2.136(19) . ? Re1 N1 2.176(18) . ? N1 N2 1.38(3) . ? N1 C4 1.35(3) . ? N3 C7 1.34(3) . ? N3 N4 1.41(3) . ? N3 C13 1.47(3) . ? C2 O2 1.12(3) . ? N6 C12 1.29(3) . ? N6 N5 1.39(3) . ? N4 C9 1.36(3) . ? C3 O3 1.15(3) . ? C13 N5 1.48(3) . ? C13 N2 1.41(3) . ? C13 C14 1.66(3) . ? C1 O1 1.06(3) . ? C9 C8 1.38(4) . ? N5 C10 1.34(3) . ? C14 O4 1.38(3) . ? C14 C15 2.16(5) . ? N2 C6 1.37(3) . ? O4 C15 1.38(4) . ? C7 C8 1.41(4) . ? C4 C5 1.29(4) . ? C5 C6 1.32(4) . ? C11 C10 1.34(4) . ? C11 C12 1.42(4) . ? C21 O6 1.08(5) . ? C20 O6 2.35(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 89.3(14) . . ? C3 Re1 C2 91.8(13) . . ? C1 Re1 C2 90.8(13) . . ? C3 Re1 N4 92.2(12) . . ? C1 Re1 N4 92.8(11) . . ? C2 Re1 N4 174.6(9) . . ? C3 Re1 N6 173.1(12) . . ? C1 Re1 N6 94.5(11) . . ? C2 Re1 N6 93.8(9) . . ? N4 Re1 N6 82.0(8) . . ? C3 Re1 N1 94.8(12) . . ? C1 Re1 N1 173.9(12) . . ? C2 Re1 N1 93.5(9) . . ? N4 Re1 N1 82.6(7) . . ? N6 Re1 N1 80.9(7) . . ? N2 N1 C4 101(2) . . ? N2 N1 Re1 117.4(15) . . ? C4 N1 Re1 142(2) . . ? C7 N3 N4 112(3) . . ? C7 N3 C13 131(3) . . ? N4 N3 C13 117(2) . . ? O2 C2 Re1 178(3) . . ? C12 N6 N5 101(2) . . ? C12 N6 Re1 134.2(19) . . ? N5 N6 Re1 123.3(15) . . ? C9 N4 N3 104(2) . . ? C9 N4 Re1 134(2) . . ? N3 N4 Re1 120.7(17) . . ? O3 C3 Re1 174(3) . . ? N5 C13 N3 110.2(17) . . ? N5 C13 N2 115(2) . . ? N3 C13 N2 107(2) . . ? N5 C13 C14 103.7(18) . . ? N3 C13 C14 105(2) . . ? N2 C13 C14 114.3(19) . . ? O1 C1 Re1 173(3) . . ? C8 C9 N4 110(3) . . ? N6 N5 C13 113.8(19) . . ? N6 N5 C10 116.0(19) . . ? C13 N5 C10 130(2) . . ? O4 C14 C13 103(2) . . ? O4 C14 C15 38.6(16) . . ? C13 C14 C15 142(2) . . ? N1 N2 C6 110(2) . . ? N1 N2 C13 122.2(18) . . ? C6 N2 C13 128(2) . . ? C15 O4 C14 103(3) . . ? N3 C7 C8 105(3) . . ? C5 C4 N1 115(3) . . ? C6 C5 C4 107(2) . . ? C9 C8 C7 108(2) . . ? C5 C6 N2 107(2) . . ? C10 C11 C12 108(2) . . ? O4 C15 C14 38.6(17) . . ? C11 C10 N5 103(2) . . ? N6 C12 C11 112(2) . . ? C21 O6 C20 127(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.635 _refine_diff_density_min -1.133 _refine_diff_density_rms 0.314