# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Roger Alberto' _publ_contact_author_email ARIEL@ACI.UNIZH.CH _publ_section_title ; Ligand-Mediated Decarbonylation as an Efficient Synthetic Method to Re(I) and Re(II) Dicarbonyl Complexes ; loop_ _publ_author_name 'Roger Alberto' 'Bernhard Spingler' 'Fabio Zobi' # Attachment 'Structure_2.cif' data_fz011107 _database_code_depnum_ccdc_archive 'CCDC 685370' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H16 Br2 N3 O4 Re' _chemical_formula_weight 576.27 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 8.2862(6) _cell_length_b 14.8528(8) _cell_length_c 11.8676(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.936(5) _cell_angle_gamma 90.00 _cell_volume 1460.39(15) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 7356 _cell_measurement_theta_min 2.4559 _cell_measurement_theta_max 32.6725 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 13.805 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.22595 _exptl_absorpt_correction_T_max 0.50000 _exptl_absorpt_process_details ? _exptl_special_details ; Crystal was non-merohedrally twinned by a 180 degree rotation around 0 0 1 at an estimated ratio of 55:45. The two components were integrated with the TWIN routine of CrysalisPro to give a HKLF 5 file. ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur Ruby' _diffrn_measurement_method '/o oscillation scan' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6291 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.2155 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 30.51 _reflns_number_total 6291 _reflns_number_gt 3111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis RED (Oxford, 2007)' _computing_cell_refinement 'CrysAlis RED (Oxford, 2007)' _computing_data_reduction 'CrysAlis RED (Oxford, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0385P)^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 6291 _refine_ls_number_parameters 175 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.1007 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1426 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 0.755 _refine_ls_restrained_S_all 0.751 _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 0.75251(7) 0.86348(2) 0.16889(3) 0.01587(10) Uani 1 1 d . . . Br1 Br 0.7544(2) 0.69593(7) 0.21967(10) 0.0268(2) Uani 1 1 d . . . Br2 Br 0.74178(19) 1.22009(8) -0.25610(9) 0.0267(2) Uani 1 1 d . . . C1 C 0.762(2) 0.9654(8) 0.0655(10) 0.031(3) Uani 1 1 d . . . C2 C 0.9189(16) 0.8292(10) 0.0616(10) 0.024(3) Uani 1 1 d . . . C3 C 0.5750(18) 0.8353(10) 0.0644(9) 0.025(3) Uani 1 1 d . . . C11 C 0.8907(16) 1.0471(10) 0.2302(10) 0.0288(19) Uani 1 1 d U . . H11A H 0.8578 1.0836 0.2958 0.035 Uiso 1 1 calc R . . H11B H 0.9406 1.0882 0.1751 0.035 Uiso 1 1 calc R . . C12 C 1.0153(15) 0.9784(9) 0.2689(10) 0.0266(19) Uani 1 1 d U . . H12A H 1.0798 1.0025 0.3331 0.032 Uiso 1 1 calc R . . H12B H 1.0894 0.9642 0.2068 0.032 Uiso 1 1 calc R . . C13 C 0.8525(14) 0.9083(9) 0.4154(9) 0.0237(18) Uani 1 1 d U . . H13A H 0.9221 0.8822 0.4757 0.028 Uiso 1 1 calc R . . H13B H 0.8393 0.9734 0.4303 0.028 Uiso 1 1 calc R . . C14 C 0.6962(14) 0.8637(8) 0.4123(9) 0.0238(18) Uani 1 1 d U . . H14A H 0.6365 0.8796 0.4811 0.029 Uiso 1 1 calc R . . H14B H 0.7128 0.7977 0.4123 0.029 Uiso 1 1 calc R . . C15 C 0.5400(15) 0.9884(9) 0.3130(10) 0.0261(19) Uani 1 1 d U . . H15A H 0.4215 0.9906 0.3218 0.031 Uiso 1 1 calc R . . H15B H 0.5907 1.0188 0.3789 0.031 Uiso 1 1 calc R . . C16 C 0.5844(15) 1.0363(10) 0.2087(9) 0.0256(19) Uani 1 1 d U . . H16B H 0.5071 1.0215 0.1469 0.031 Uiso 1 1 calc R . . H16A H 0.5825 1.1022 0.2210 0.031 Uiso 1 1 calc R . . N1 N 0.7489(17) 1.0066(5) 0.1792(8) 0.0227(18) Uani 1 1 d . . . N2 N 0.9252(13) 0.8941(7) 0.3046(8) 0.019(2) Uani 1 1 d . . . H2A H 0.9985 0.8469 0.3104 0.022 Uiso 1 1 calc R . . N3 N 0.5956(14) 0.8899(7) 0.3093(7) 0.019(2) Uani 1 1 d . . . H3A H 0.5057 0.8525 0.3041 0.022 Uiso 1 1 calc R . . O1 O 0.7758(16) 1.0026(6) -0.0300(7) 0.040(3) Uani 1 1 d . . . O2 O 1.0099(14) 0.8043(9) -0.0013(8) 0.039(3) Uani 1 1 d . . . O3 O 0.4707(12) 0.8202(8) 0.0024(7) 0.030(2) Uani 1 1 d . . . O4 O 1.2583(19) 0.6393(5) 0.0199(7) 0.042(2) 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 0.02126(17) 0.01215(15) 0.01427(15) -0.00089(17) 0.00231(13) -0.0002(3) Br1 0.0335(5) 0.0159(4) 0.0310(5) 0.0007(4) 0.0008(5) 0.0007(8) Br2 0.0234(5) 0.0289(5) 0.0279(5) -0.0015(4) 0.0025(5) 0.0002(7) C1 0.031(6) 0.030(6) 0.031(5) 0.003(5) 0.003(5) -0.002(8) C2 0.027(7) 0.019(7) 0.025(5) -0.001(5) -0.002(5) -0.001(6) C3 0.040(8) 0.013(6) 0.023(5) -0.001(4) 0.012(5) -0.004(6) C11 0.030(4) 0.027(4) 0.030(4) 0.003(4) 0.005(3) 0.003(4) C12 0.029(4) 0.020(4) 0.031(4) 0.001(3) 0.001(3) -0.004(4) C13 0.023(4) 0.024(4) 0.025(3) 0.005(3) 0.006(3) 0.006(4) C14 0.033(4) 0.014(4) 0.024(3) 0.002(3) -0.001(3) 0.008(4) C15 0.027(4) 0.020(4) 0.032(4) -0.001(4) -0.001(3) 0.004(4) C16 0.027(4) 0.023(4) 0.027(3) 0.003(3) 0.003(3) 0.006(4) N1 0.020(4) 0.009(3) 0.039(5) 0.006(4) -0.003(5) 0.003(6) N2 0.025(5) 0.006(5) 0.025(4) 0.001(4) 0.004(4) 0.003(4) N3 0.031(6) 0.008(5) 0.017(4) 0.002(3) 0.005(4) -0.002(4) O1 0.074(8) 0.019(4) 0.027(4) 0.015(3) 0.007(5) 0.001(6) O2 0.050(6) 0.040(7) 0.027(4) -0.007(4) 0.019(4) 0.005(6) O3 0.030(5) 0.034(6) 0.025(4) -0.001(4) -0.010(4) -0.001(5) O4 0.077(7) 0.017(3) 0.032(4) 0.007(4) 0.008(5) -0.002(8) _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 1.951(12) . ? Re1 C3 1.953(15) . ? Re1 C2 1.960(13) . ? Re1 N1 2.129(8) . ? Re1 N3 2.166(10) . ? Re1 N2 2.184(11) . ? Re1 Br1 2.5605(10) . ? C1 O1 1.268(14) . ? C1 N1 1.486(14) . ? C2 O2 1.131(16) . ? C3 O3 1.148(16) . ? C11 N1 1.445(19) . ? C11 C12 1.518(18) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N2 1.522(16) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.454(16) . ? C13 N2 1.471(14) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N3 1.519(15) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.480(17) . ? C15 N3 1.535(16) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N1 1.480(18) . ? C16 H16B 0.9900 . ? C16 H16A 0.9900 . ? N2 H2A 0.9300 . ? N3 H3A 0.9300 . ? 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 78.8(6) . . ? C1 Re1 C2 75.9(6) . . ? C3 Re1 C2 93.6(4) . . ? C1 Re1 N1 42.4(4) . . ? C3 Re1 N1 103.8(5) . . ? C2 Re1 N1 107.9(6) . . ? C1 Re1 N3 112.0(5) . . ? C3 Re1 N3 94.1(4) . . ? C2 Re1 N3 169.9(5) . . ? N1 Re1 N3 76.5(4) . . ? C1 Re1 N2 105.6(5) . . ? C3 Re1 N2 171.8(4) . . ? C2 Re1 N2 94.2(4) . . ? N1 Re1 N2 76.1(4) . . ? N3 Re1 N2 77.8(3) . . ? C1 Re1 Br1 154.4(4) . . ? C3 Re1 Br1 86.7(4) . . ? C2 Re1 Br1 84.2(4) . . ? N1 Re1 Br1 163.1(3) . . ? N3 Re1 Br1 89.8(3) . . ? N2 Re1 Br1 91.6(3) . . ? O1 C1 N1 129.9(10) . . ? O1 C1 Re1 154.9(10) . . ? N1 C1 Re1 75.2(6) . . ? O2 C2 Re1 175.6(14) . . ? O3 C3 Re1 178.8(13) . . ? N1 C11 C12 113.1(11) . . ? N1 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N1 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C11 C12 N2 107.6(10) . . ? C11 C12 H12A 110.2 . . ? N2 C12 H12A 110.2 . . ? C11 C12 H12B 110.2 . . ? N2 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? C14 C13 N2 106.8(10) . . ? C14 C13 H13A 110.4 . . ? N2 C13 H13A 110.4 . . ? C14 C13 H13B 110.4 . . ? N2 C13 H13B 110.4 . . ? H13A C13 H13B 108.6 . . ? C13 C14 N3 112.4(9) . . ? C13 C14 H14A 109.1 . . ? N3 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? N3 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C16 C15 N3 110.8(10) . . ? C16 C15 H15A 109.5 . . ? N3 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N1 C16 C15 107.3(10) . . ? N1 C16 H16B 110.3 . . ? C15 C16 H16B 110.3 . . ? N1 C16 H16A 110.3 . . ? C15 C16 H16A 110.3 . . ? H16B C16 H16A 108.5 . . ? C11 N1 C16 121.5(9) . . ? C11 N1 C1 118.7(12) . . ? C16 N1 C1 114.7(12) . . ? C11 N1 Re1 115.3(9) . . ? C16 N1 Re1 108.9(8) . . ? C1 N1 Re1 62.4(5) . . ? C13 N2 C12 109.9(10) . . ? C13 N2 Re1 114.6(8) . . ? C12 N2 Re1 106.6(7) . . ? C13 N2 H2A 108.5 . . ? C12 N2 H2A 108.5 . . ? Re1 N2 H2A 108.5 . . ? C14 N3 C15 112.5(9) . . ? C14 N3 Re1 104.1(7) . . ? C15 N3 Re1 112.3(7) . . ? C14 N3 H3A 109.3 . . ? C15 N3 H3A 109.3 . . ? Re1 N3 H3A 109.3 . . ? 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 -58(3) . . . . ? C2 Re1 C1 O1 38(3) . . . . ? N1 Re1 C1 O1 176(4) . . . . ? N3 Re1 C1 O1 -148(3) . . . . ? N2 Re1 C1 O1 129(3) . . . . ? Br1 Re1 C1 O1 -2(4) . . . . ? C3 Re1 C1 N1 125.4(9) . . . . ? C2 Re1 C1 N1 -138.0(10) . . . . ? N3 Re1 C1 N1 35.4(10) . . . . ? N2 Re1 C1 N1 -47.5(9) . . . . ? Br1 Re1 C1 N1 -178.1(7) . . . . ? C1 Re1 C2 O2 -129(15) . . . . ? C3 Re1 C2 O2 -52(15) . . . . ? N1 Re1 C2 O2 -157(15) . . . . ? N3 Re1 C2 O2 88(15) . . . . ? N2 Re1 C2 O2 126(15) . . . . ? Br1 Re1 C2 O2 35(15) . . . . ? C1 Re1 C3 O3 -18(53) . . . . ? C2 Re1 C3 O3 -93(53) . . . . ? N1 Re1 C3 O3 16(53) . . . . ? N3 Re1 C3 O3 93(53) . . . . ? N2 Re1 C3 O3 105(52) . . . . ? Br1 Re1 C3 O3 -177(100) . . . . ? N1 C11 C12 N2 -31.9(13) . . . . ? N2 C13 C14 N3 -50.2(12) . . . . ? N3 C15 C16 N1 -40.9(14) . . . . ? C12 C11 N1 C16 134.4(10) . . . . ? C12 C11 N1 C1 -72.0(13) . . . . ? C12 C11 N1 Re1 -1.0(12) . . . . ? C15 C16 N1 C11 -83.3(12) . . . . ? C15 C16 N1 C1 122.1(10) . . . . ? C15 C16 N1 Re1 54.5(11) . . . . ? O1 C1 N1 C11 -73(2) . . . . ? Re1 C1 N1 C11 105.3(9) . . . . ? O1 C1 N1 C16 83(2) . . . . ? Re1 C1 N1 C16 -99.3(9) . . . . ? O1 C1 N1 Re1 -178(2) . . . . ? C1 Re1 N1 C11 -110.6(13) . . . . ? C3 Re1 N1 C11 -166.1(8) . . . . ? C2 Re1 N1 C11 -67.7(9) . . . . ? N3 Re1 N1 C11 102.9(8) . . . . ? N2 Re1 N1 C11 22.3(8) . . . . ? Br1 Re1 N1 C11 66.5(17) . . . . ? C1 Re1 N1 C16 108.6(12) . . . . ? C3 Re1 N1 C16 53.2(8) . . . . ? C2 Re1 N1 C16 151.6(7) . . . . ? N3 Re1 N1 C16 -37.8(7) . . . . ? N2 Re1 N1 C16 -118.4(8) . . . . ? Br1 Re1 N1 C16 -74.2(16) . . . . ? C3 Re1 N1 C1 -55.5(10) . . . . ? C2 Re1 N1 C1 43.0(10) . . . . ? N3 Re1 N1 C1 -146.5(10) . . . . ? N2 Re1 N1 C1 133.0(10) . . . . ? Br1 Re1 N1 C1 177.1(11) . . . . ? C14 C13 N2 C12 142.1(10) . . . . ? C14 C13 N2 Re1 22.1(11) . . . . ? C11 C12 N2 C13 -76.1(12) . . . . ? C11 C12 N2 Re1 48.6(10) . . . . ? C1 Re1 N2 C13 114.3(9) . . . . ? C3 Re1 N2 C13 -7(4) . . . . ? C2 Re1 N2 C13 -169.1(9) . . . . ? N1 Re1 N2 C13 83.5(9) . . . . ? N3 Re1 N2 C13 4.6(7) . . . . ? Br1 Re1 N2 C13 -84.8(8) . . . . ? C1 Re1 N2 C12 -7.5(9) . . . . ? C3 Re1 N2 C12 -129(3) . . . . ? C2 Re1 N2 C12 69.0(8) . . . . ? N1 Re1 N2 C12 -38.4(7) . . . . ? N3 Re1 N2 C12 -117.2(8) . . . . ? Br1 Re1 N2 C12 153.3(7) . . . . ? C13 C14 N3 C15 -68.5(12) . . . . ? C13 C14 N3 Re1 53.2(10) . . . . ? C16 C15 N3 C14 127.0(10) . . . . ? C16 C15 N3 Re1 9.9(13) . . . . ? C1 Re1 N3 C14 -130.6(8) . . . . ? C3 Re1 N3 C14 149.8(8) . . . . ? C2 Re1 N3 C14 10(3) . . . . ? N1 Re1 N3 C14 -106.9(8) . . . . ? N2 Re1 N3 C14 -28.5(6) . . . . ? Br1 Re1 N3 C14 63.1(7) . . . . ? C1 Re1 N3 C15 -8.7(10) . . . . ? C3 Re1 N3 C15 -88.2(9) . . . . ? C2 Re1 N3 C15 132(3) . . . . ? N1 Re1 N3 C15 15.0(8) . . . . ? N2 Re1 N3 C15 93.4(9) . . . . ? Br1 Re1 N3 C15 -174.9(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.780 _refine_diff_density_min -2.565 _refine_diff_density_rms 0.401 # Attachment 'Structure3a_final.cif' data_fz250308 _database_code_depnum_ccdc_archive 'CCDC 685371' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H13 Br N3 O2 Re' _chemical_formula_weight 425.30 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 7.1668(1) _cell_length_b 12.1894(3) _cell_length_c 11.8617(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.295(2) _cell_angle_gamma 90.00 _cell_volume 1004.14(3) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 5057 _cell_measurement_theta_min 2.4292 _cell_measurement_theta_max 34.6759 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.813 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 16.054 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.06421 _exptl_absorpt_correction_T_max 0.38000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur Ruby' _diffrn_measurement_method '/o oscillation scan' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9092 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 33.14 _reflns_number_total 3808 _reflns_number_gt 3024 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis RED (Oxford, 2007)' _computing_cell_refinement 'CrysAlis RED (Oxford, 2007)' _computing_data_reduction 'CrysAlis RED (Oxford, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0431P)^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 3808 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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 0.76405(2) 0.152177(14) 0.366181(14) 0.01484(6) Uani 1 1 d . . . Br1 Br 0.71987(7) 0.11156(4) 0.57284(4) 0.02262(11) Uani 1 1 d . . . C1 C 1.0278(7) 0.1854(4) 0.4108(4) 0.0205(9) Uani 1 1 d . . . C2 C 0.7292(6) 0.3034(5) 0.3657(4) 0.0208(10) Uani 1 1 d . . . C3 C 0.3965(7) 0.1661(4) 0.1802(4) 0.0222(10) Uani 1 1 d . . . H3A H 0.4046 0.2470 0.1865 0.027 Uiso 1 1 calc R . . H3B H 0.2626 0.1458 0.1405 0.027 Uiso 1 1 calc R . . C4 C 0.5342(7) 0.1240(4) 0.1118(4) 0.0200(9) Uani 1 1 d . . . H4A H 0.5033 0.0466 0.0895 0.024 Uiso 1 1 calc R . . H4B H 0.5187 0.1675 0.0395 0.024 Uiso 1 1 calc R . . C5 C 0.8522(7) 0.0336(4) 0.1651(4) 0.0232(10) Uani 1 1 d . . . H5A H 0.9914 0.0490 0.1948 0.028 Uiso 1 1 calc R . . H5B H 0.8274 0.0161 0.0812 0.028 Uiso 1 1 calc R . . C6 C 0.7962(8) -0.0622(4) 0.2295(4) 0.0255(10) Uani 1 1 d . . . H6A H 0.6636 -0.0860 0.1912 0.031 Uiso 1 1 calc R . . H6B H 0.8844 -0.1246 0.2288 0.031 Uiso 1 1 calc R . . N1 N 0.4510(6) 0.1160(4) 0.2972(3) 0.0207(8) Uani 1 1 d . . . H1C H 0.4299 0.0415 0.2927 0.025 Uiso 1 1 calc R . . H1D H 0.3804 0.1461 0.3446 0.025 Uiso 1 1 calc R . . N2 N 0.7381(6) 0.1318(3) 0.1819(3) 0.0191(8) Uani 1 1 d . . . H2C H 0.7935 0.1928 0.1560 0.023 Uiso 1 1 calc R . . N3 N 0.8070(6) -0.0285(4) 0.3510(3) 0.0218(8) Uani 1 1 d . . . H3C H 0.9253 -0.0478 0.3973 0.026 Uiso 1 1 calc R . . H3D H 0.7143 -0.0654 0.3776 0.026 Uiso 1 1 calc R . . O1 O 1.1896(5) 0.2103(3) 0.4388(3) 0.0275(8) Uani 1 1 d . . . O2 O 0.7153(6) 0.4000(3) 0.3647(3) 0.0293(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 0.01800(8) 0.01352(9) 0.01310(9) -0.00035(6) 0.00404(6) 0.00091(7) Br1 0.0307(2) 0.0213(2) 0.0167(2) 0.00091(17) 0.00748(18) 0.0024(2) C1 0.029(2) 0.016(2) 0.019(2) 0.0031(17) 0.0095(18) 0.0030(19) C2 0.019(2) 0.029(3) 0.016(2) -0.0004(18) 0.0044(17) 0.0000(18) C3 0.021(2) 0.023(3) 0.022(2) 0.0022(18) 0.0048(17) 0.0007(18) C4 0.022(2) 0.020(2) 0.018(2) 0.0011(17) 0.0038(17) 0.0000(17) C5 0.028(2) 0.024(3) 0.018(2) -0.0045(18) 0.0065(18) 0.006(2) C6 0.035(3) 0.018(2) 0.022(2) -0.0042(18) 0.002(2) 0.005(2) N1 0.0198(17) 0.023(2) 0.021(2) 0.0024(16) 0.0079(15) -0.0035(16) N2 0.0213(18) 0.020(2) 0.0165(19) -0.0013(14) 0.0059(15) -0.0027(15) N3 0.0262(19) 0.018(2) 0.0203(19) 0.0000(15) 0.0047(15) 0.0008(16) O1 0.0223(16) 0.030(2) 0.0310(19) -0.0015(15) 0.0072(14) -0.0017(15) O2 0.042(2) 0.018(2) 0.029(2) -0.0009(14) 0.0100(17) 0.0040(17) _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 C2 1.859(6) . ? Re1 C1 1.877(5) . ? Re1 N2 2.162(4) . ? Re1 N1 2.234(4) . ? Re1 N3 2.237(4) . ? Re1 Br1 2.5958(5) . ? C1 O1 1.165(6) . ? C2 O2 1.182(7) . ? C3 N1 1.478(6) . ? C3 C4 1.515(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.495(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N2 1.490(6) . ? C5 C6 1.504(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N3 1.482(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N1 H1C 0.9200 . ? N1 H1D 0.9200 . ? N2 H2C 0.9300 . ? N3 H3C 0.9200 . ? N3 H3D 0.9200 . ? 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 C2 Re1 C1 85.0(2) . . ? C2 Re1 N2 97.62(17) . . ? C1 Re1 N2 97.99(17) . . ? C2 Re1 N1 94.15(18) . . ? C1 Re1 N1 175.02(17) . . ? N2 Re1 N1 77.25(15) . . ? C2 Re1 N3 175.14(17) . . ? C1 Re1 N3 94.93(19) . . ? N2 Re1 N3 77.57(15) . . ? N1 Re1 N3 85.53(16) . . ? C2 Re1 Br1 98.30(14) . . ? C1 Re1 Br1 97.13(14) . . ? N2 Re1 Br1 158.89(11) . . ? N1 Re1 Br1 87.85(10) . . ? N3 Re1 Br1 86.54(10) . . ? O1 C1 Re1 177.3(5) . . ? O2 C2 Re1 177.0(4) . . ? N1 C3 C4 107.9(4) . . ? N1 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? N1 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N2 C4 C3 110.9(4) . . ? N2 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.0 . . ? N2 C5 C6 109.4(4) . . ? N2 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? N2 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? N3 C6 C5 108.8(4) . . ? N3 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? N3 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C3 N1 Re1 105.7(3) . . ? C3 N1 H1C 110.6 . . ? Re1 N1 H1C 110.6 . . ? C3 N1 H1D 110.6 . . ? Re1 N1 H1D 110.6 . . ? H1C N1 H1D 108.7 . . ? C5 N2 C4 111.6(4) . . ? C5 N2 Re1 108.3(3) . . ? C4 N2 Re1 113.5(3) . . ? C5 N2 H2C 107.8 . . ? C4 N2 H2C 107.8 . . ? Re1 N2 H2C 107.8 . . ? C6 N3 Re1 112.1(3) . . ? C6 N3 H3C 109.2 . . ? Re1 N3 H3C 109.2 . . ? C6 N3 H3D 109.2 . . ? Re1 N3 H3D 109.2 . . ? H3C N3 H3D 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 Re1 C1 O1 5(9) . . . . ? N2 Re1 C1 O1 102(9) . . . . ? N1 Re1 C1 O1 85(9) . . . . ? N3 Re1 C1 O1 -180(100) . . . . ? Br1 Re1 C1 O1 -92(9) . . . . ? C1 Re1 C2 O2 23(7) . . . . ? N2 Re1 C2 O2 -74(7) . . . . ? N1 Re1 C2 O2 -152(7) . . . . ? N3 Re1 C2 O2 -66(8) . . . . ? Br1 Re1 C2 O2 120(7) . . . . ? N1 C3 C4 N2 -47.4(5) . . . . ? N2 C5 C6 N3 -51.1(5) . . . . ? C4 C3 N1 Re1 53.2(4) . . . . ? C2 Re1 N1 C3 63.0(3) . . . . ? C1 Re1 N1 C3 -17(2) . . . . ? N2 Re1 N1 C3 -33.9(3) . . . . ? N3 Re1 N1 C3 -112.2(3) . . . . ? Br1 Re1 N1 C3 161.2(3) . . . . ? C6 C5 N2 C4 -74.4(5) . . . . ? C6 C5 N2 Re1 51.2(4) . . . . ? C3 C4 N2 C5 139.9(4) . . . . ? C3 C4 N2 Re1 17.2(5) . . . . ? C2 Re1 N2 C5 152.1(3) . . . . ? C1 Re1 N2 C5 66.1(3) . . . . ? N1 Re1 N2 C5 -115.4(3) . . . . ? N3 Re1 N2 C5 -27.2(3) . . . . ? Br1 Re1 N2 C5 -69.2(4) . . . . ? C2 Re1 N2 C4 -83.5(3) . . . . ? C1 Re1 N2 C4 -169.4(3) . . . . ? N1 Re1 N2 C4 9.1(3) . . . . ? N3 Re1 N2 C4 97.2(3) . . . . ? Br1 Re1 N2 C4 55.2(5) . . . . ? C5 C6 N3 Re1 26.4(5) . . . . ? C2 Re1 N3 C6 -8(2) . . . . ? C1 Re1 N3 C6 -96.8(3) . . . . ? N2 Re1 N3 C6 0.3(3) . . . . ? N1 Re1 N3 C6 78.2(3) . . . . ? Br1 Re1 N3 C6 166.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.883 _refine_diff_density_min -2.761 _refine_diff_density_rms 0.279