# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '3518_web_deposit_cif_file_0_Dr.OlivierBlacque_1292578226.cif' _publ_section_synopsis . #Added by publCIF _publ_section_figure_captions ; ; #Added by publCIF _audit_update_record ; 2010-12-16 # Formatted by publCIF ; # #------------------------------------------------------------------------- #2 Person making the deposition # _publ_contact_author 'Dr. Blacque, Olivier' _publ_contact_author_email oblacque@aci.uzh.ch _publ_contact_author_fax '+41 44 63 54 681' _publ_contact_author_phone '+41 44 63 54 651' #------------------------------------------------------------------------- #3 Publication details # # Provide these details if the structure has been published, # accepted or submitted for publication # # The CCDC journal deposition number, eg. 182/357, # should be included only if it has been assigned by the journal # # #------------------------------------------------------------------------- #4 Chemical and physical data # # Note that the units for melting point are Kelvin # The compound_id is the identifier for the compound in the published # paper, eg. 4a, II, etc. # Provide a brief description of any significant biological activity, # eg. antimalarial activity # If the compound exhibits polymorphism provide brief details, # eg. monoclinic form, low-temperature phase, etc. # For chemdiag leave blank - no longer necessary # #------------------------------------------------------------------------- #5 Other data relating to the structure determination and refinement # # Record the radiation type if not X-rays, eg. neutron # Record the temperature of the data collection (Kelvin) # if not room-temperature # Record R_squared if this is the only reliability factor given by # your refinement program # Describe briefly any disorder, eg. t-Butyl C31-33 disordered over # two sites with occupancies 0.6 and 0.4 # Under ccdc_comments record any other important information _publ_section_exptl_refinement ; In the crystal structure of 3, the rhenium center lies on a special position. The complete molecule is generated by a crystallographic 2-fold axis. In the crystal structure of 6, the pyrazine ring lies on a special position. The complete molecule is generated by a center of inversion located in the middle of the ring. The crystal structure of 9 exhibits substitutional disorders for two bromide ligands. During the crystallization in the dichloromethane solution, the tribromo compound C~6~H~4~Br~3~N~2~O~2~Re decomposes into the bromo-dichloro analogous C~6~H~4~BrCl~2~N~2~O~2~Re. The disorders were treated with help of the EXYZ and EADP commands of SHELXL97 and 50% occupancy was used for both Br and Cl on two positions. The third bromide remained with full occupancy (as suggested by a site-occupancy refinement). In the crystal structure of 10, solvent molecules of dichloromethane co-crystallized with the rhenium species in a ratio 1:1. The mutually trans Br and CO ligands are disordered over two sets of positions with site-occupancy factors of 0.6796(14) and 0.3204(14). In all structures, the hydrogen positions were calculated after each cycle of refinement using a riding model, with C-H = 0.93 \%A and U~iso~(H) = 1.2U~eq~(C) for aromatic H atoms, with C-H = 0.97 \%A and U~iso~(H) = 1.2U~eq~(C) for methylene H atoms, and with C-H = 0.96 \%A and U~iso~(H) = 1.5U~eq~(C) for methyl H atoms. ; #Added by publCIF #------------------------------------------------------------------------- #6 Include your "standard" CIF file here # It should contain the following data items: # unit cell parameters and volume, z value, space group symbol, # R-factor(s), atomic coordinates with standard deviations, # occupancy factors, bond lengths and bond angles # Other data items may be present but will not necessarily be # included in the Cambridge Structural Database # # Do NOT include structure factors # # #------------------------------------------------------------------------- #SUBMISSION INFORMATION # # For a journal send the form to the address specified by the journal # # For a private communication to the CCDC send the form to the address # deposit@ccdc.cam.ac.uk # # For up-to-date information on deposition procedures, check the website # http://www.ccdc.cam.ac.uk/ _publ_section_comment ; (type here to add) ; _publ_section_abstract ; (type here to add abstract) ; _publ_contact_letter ; Please consider this CIF for publication. I certify that this contibution is the original work of those listed as authors; that it has not been published before (in any language or medium) and is not being considered for publication elsewhere; that all authors concur with and are aware of the submission; that all workers involved in the study are listed as authors or given proper credit in the acknowledgements; that I have obtained permission for and acknowledged the source of any excerpts from other copyright works; and that to the best of my knowledge the paper contains no statements which are libellous, unlawful or in any way actionable. All coauthors have made significant scientific contributions to the work reported, including the ideas and their execution, and share responsibility and accountability for the results. ; _publ_requested_category FM # TITLE AND AUTHOR LIST _publ_section_title ; Reactivity of 17e^-^ complex [Re^II^Br~4~(CO)~2~]^2- ^with bridging aromatic ligands. Characterization and CO-releasing properties. ; loop_ _publ_author_name _publ_author_address _publ_author_footnote _publ_author_email F.Zobi ; Institute of Inorganic Chemistry, Winterthurerstrasse 190, CH-8057, Zuerich, Switzerland ; . . O.Blacque ; Institute of Inorganic Chemistry, Winterthurerstrasse 190, CH-8057, Zuerich, Switzerland ; . . _publ_contact_author_name 'Dr. Blacque, Olivier' #----------------------------------------------------------------------------# data_2 _database_code_depnum_ccdc_archive 'CCDC 805064' #TrackingRef '3518_web_deposit_cif_file_0_Dr.OlivierBlacque_1292578226.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2,2'-bipyrimidine-\k^2^N^1^,N^1'^)(dibromo)dicarbonylrhenium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 Br2 N4 O2 Re' _chemical_formula_sum 'C10 H6 Br2 N4 O2 Re' _chemical_formula_weight 560.20 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 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.3844(2) _cell_length_b 10.9260(2) _cell_length_c 13.6043(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1394.90(5) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 6730 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 32.70 _exptl_crystal_description triangular-shape _exptl_crystal_colour red _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 14.442 _exptl_absorpt_correction_T_min 0.459 _exptl_absorpt_correction_T_max 0.640 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55. Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby Oxford Diffraction (2007). Oxford Diffraction Ltd., Xcalibur CCD system ; _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 15496 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _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 2.39 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2844 _reflns_number_gt 2508 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_structure_solution ; SHELXS97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_structure_refinement ; SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_molecular_graphics ; ORTEP-3 for Windows, Version 2.01. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. ; _computing_publication_material ; WinGX -- An integrated system of Windows programs for the solution, refinement and analysis of single crystal X-ray diffraction data, Version 1.70.01. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. PLATON for Windows, Version 1.12. Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. ; _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 'w=1/[\s^2^(Fo^2^)+(0.0224P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H. D. (1983). Acta Cryst. A39, 876-881. 1203 Friedel pairs' _refine_ls_abs_structure_Flack -0.019(13) _refine_ls_number_reflns 2844 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0511 _refine_ls_wR_factor_gt 0.0502 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _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 0.38915(3) -0.09656(3) 0.59928(2) 0.02436(8) Uani 1 1 d . . . Br1 Br 0.65500(7) -0.09303(9) 0.62632(5) 0.0413(2) Uani 1 1 d . . . Br2 Br 0.13663(8) -0.07871(8) 0.54559(6) 0.0453(2) Uani 1 1 d . . . C1 C 0.3749(8) -0.2728(7) 0.6136(5) 0.0350(17) Uani 1 1 d . . . C2 C 0.3446(7) -0.0959(9) 0.7400(6) 0.042(2) Uani 1 1 d . . . C3 C 0.4491(7) -0.1681(6) 0.3789(5) 0.0294(18) Uani 1 1 d . . . H3 H 0.4223 -0.2469 0.3971 0.035 Uiso 1 1 calc R . . C4 C 0.4972(7) -0.1468(7) 0.2856(5) 0.0272(18) Uani 1 1 d . . . H4 H 0.5023 -0.2093 0.2393 0.033 Uiso 1 1 calc R . . C5 C 0.5375(7) -0.0296(7) 0.2632(5) 0.0281(18) Uani 1 1 d . . . H5 H 0.5762 -0.0144 0.2015 0.034 Uiso 1 1 calc R . . C6 C 0.4733(7) 0.0370(6) 0.4144(5) 0.0217(15) Uani 1 1 d . . . C7 C 0.4409(7) 0.1372(6) 0.4832(5) 0.0260(16) Uani 1 1 d . . . C8 C 0.3625(7) 0.1871(7) 0.6376(5) 0.0342(19) Uani 1 1 d . . . H8 H 0.3371 0.1649 0.7012 0.041 Uiso 1 1 calc R . . C9 C 0.3591(7) 0.3070(7) 0.6114(6) 0.041(2) Uani 1 1 d . . . H9 H 0.3281 0.3676 0.6544 0.049 Uiso 1 1 calc R . . C10 C 0.4048(8) 0.3338(6) 0.5166(6) 0.0360(18) Uani 1 1 d . . . H10 H 0.4075 0.4153 0.4970 0.043 Uiso 1 1 calc R . . N1 N 0.4401(5) -0.0766(5) 0.4447(4) 0.0215(13) Uani 1 1 d . . . N2 N 0.4016(5) 0.0998(5) 0.5738(4) 0.0245(11) Uani 1 1 d . . . N3 N 0.5241(6) 0.0638(5) 0.3256(4) 0.0293(14) Uani 1 1 d . . . N4 N 0.4439(7) 0.2507(5) 0.4541(5) 0.0336(17) Uani 1 1 d . . . O1 O 0.3628(7) -0.3737(5) 0.6268(4) 0.0546(17) Uani 1 1 d . . . O2 O 0.3178(5) -0.1010(8) 0.8163(4) 0.0617(18) 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 0.02501(12) 0.02823(13) 0.01984(12) 0.00450(15) 0.00279(12) 0.00027(16) Br1 0.0274(4) 0.0651(5) 0.0315(4) 0.0018(5) -0.0019(3) 0.0017(4) Br2 0.0337(4) 0.0527(5) 0.0496(5) 0.0052(4) 0.0000(4) -0.0018(4) C1 0.033(4) 0.040(4) 0.032(4) 0.003(4) 0.016(4) 0.008(4) C2 0.019(3) 0.067(6) 0.042(5) 0.020(6) -0.001(3) 0.009(5) C3 0.031(4) 0.022(4) 0.036(5) -0.001(3) -0.002(3) -0.003(3) C4 0.031(4) 0.028(4) 0.022(4) -0.007(4) -0.005(3) 0.007(3) C5 0.027(4) 0.042(5) 0.016(4) -0.006(4) 0.005(3) -0.005(4) C6 0.022(3) 0.028(4) 0.015(4) 0.007(3) -0.005(3) -0.004(3) C7 0.024(3) 0.033(4) 0.021(4) 0.004(3) -0.002(3) -0.009(3) C8 0.034(4) 0.046(5) 0.023(4) -0.009(4) -0.002(4) -0.004(4) C9 0.035(5) 0.038(4) 0.050(6) -0.018(4) 0.007(4) 0.001(4) C10 0.049(5) 0.022(4) 0.037(4) -0.007(3) 0.007(4) -0.011(4) N1 0.025(3) 0.024(3) 0.016(3) 0.005(3) -0.003(2) -0.002(3) N2 0.020(3) 0.028(3) 0.026(3) 0.003(3) 0.001(2) 0.000(3) N3 0.034(3) 0.028(3) 0.026(3) 0.000(3) 0.003(3) -0.006(3) N4 0.049(4) 0.023(3) 0.028(4) -0.006(3) 0.008(3) -0.004(3) O1 0.070(4) 0.034(3) 0.060(4) 0.016(3) 0.027(3) 0.006(3) O2 0.039(3) 0.110(5) 0.036(3) 0.003(5) 0.001(3) 0.017(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 C1 1.940(7) . ? Re1 C2 1.960(8) . ? Re1 N1 2.168(5) . ? Re1 N2 2.177(6) . ? Re1 Br2 2.4874(9) . ? Re1 Br1 2.5221(7) . ? C1 O1 1.123(8) . ? C2 O2 1.069(8) . ? C3 N1 1.345(8) . ? C3 C4 1.367(9) . ? C3 H3 0.9300 . ? C4 C5 1.370(10) . ? C4 H4 0.9300 . ? C5 N3 1.333(9) . ? C5 H5 0.9300 . ? C6 N3 1.331(9) . ? C6 N1 1.345(8) . ? C6 C7 1.473(10) . ? C7 N4 1.302(8) . ? C7 N2 1.349(8) . ? C8 N2 1.340(8) . ? C8 C9 1.358(10) . ? C8 H8 0.9300 . ? C9 C10 1.391(10) . ? C9 H9 0.9300 . ? C10 N4 1.296(8) . ? C10 H10 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 C2 83.7(4) . . ? C1 Re1 N1 102.3(3) . . ? C2 Re1 N1 174.0(3) . . ? C1 Re1 N2 176.5(3) . . ? C2 Re1 N2 99.4(3) . . ? N1 Re1 N2 74.60(19) . . ? C1 Re1 Br2 92.4(2) . . ? C2 Re1 Br2 94.79(18) . . ? N1 Re1 Br2 85.26(14) . . ? N2 Re1 Br2 85.82(13) . . ? C1 Re1 Br1 93.9(2) . . ? C2 Re1 Br1 93.91(19) . . ? N1 Re1 Br1 85.51(14) . . ? N2 Re1 Br1 87.42(13) . . ? Br2 Re1 Br1 169.74(3) . . ? O1 C1 Re1 176.1(7) . . ? O2 C2 Re1 176.6(10) . . ? N1 C3 C4 120.8(7) . . ? N1 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 117.2(7) . . ? C3 C4 H4 121.4 . . ? C5 C4 H4 121.4 . . ? N3 C5 C4 123.2(6) . . ? N3 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? N3 C6 N1 124.3(6) . . ? N3 C6 C7 119.2(6) . . ? N1 C6 C7 116.3(6) . . ? N4 C7 N2 124.9(7) . . ? N4 C7 C6 120.7(6) . . ? N2 C7 C6 114.3(6) . . ? N2 C8 C9 121.6(7) . . ? N2 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C8 C9 C10 116.0(7) . . ? C8 C9 H9 122.0 . . ? C10 C9 H9 122.0 . . ? N4 C10 C9 123.3(7) . . ? N4 C10 H10 118.4 . . ? C9 C10 H10 118.4 . . ? C6 N1 C3 117.9(6) . . ? C6 N1 Re1 116.2(5) . . ? C3 N1 Re1 125.8(5) . . ? C8 N2 C7 116.8(6) . . ? C8 N2 Re1 125.7(5) . . ? C7 N2 Re1 117.3(5) . . ? C6 N3 C5 116.3(6) . . ? C10 N4 C7 117.4(7) . . ? 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 C3 C4 C5 1.1(10) . . . . ? C3 C4 C5 N3 -4.0(11) . . . . ? N3 C6 C7 N4 8.9(10) . . . . ? N1 C6 C7 N4 -167.0(6) . . . . ? N3 C6 C7 N2 -174.7(6) . . . . ? N1 C6 C7 N2 9.4(8) . . . . ? N2 C8 C9 C10 -2.9(11) . . . . ? C8 C9 C10 N4 2.5(12) . . . . ? N3 C6 N1 C3 -5.0(9) . . . . ? C7 C6 N1 C3 170.7(6) . . . . ? N3 C6 N1 Re1 171.3(5) . . . . ? C7 C6 N1 Re1 -13.0(7) . . . . ? C4 C3 N1 C6 3.1(9) . . . . ? C4 C3 N1 Re1 -172.8(5) . . . . ? C1 Re1 N1 C6 -172.5(5) . . . . ? N2 Re1 N1 C6 9.1(4) . . . . ? Br2 Re1 N1 C6 96.1(4) . . . . ? Br1 Re1 N1 C6 -79.4(4) . . . . ? C1 Re1 N1 C3 3.5(6) . . . . ? N2 Re1 N1 C3 -174.9(6) . . . . ? Br2 Re1 N1 C3 -87.9(5) . . . . ? Br1 Re1 N1 C3 96.6(5) . . . . ? C9 C8 N2 C7 1.7(10) . . . . ? C9 C8 N2 Re1 -172.5(5) . . . . ? N4 C7 N2 C8 0.3(10) . . . . ? C6 C7 N2 C8 -176.0(6) . . . . ? N4 C7 N2 Re1 175.0(6) . . . . ? C6 C7 N2 Re1 -1.3(7) . . . . ? C2 Re1 N2 C8 -10.1(6) . . . . ? N1 Re1 N2 C8 170.3(6) . . . . ? Br2 Re1 N2 C8 84.0(5) . . . . ? Br1 Re1 N2 C8 -103.7(5) . . . . ? C2 Re1 N2 C7 175.7(5) . . . . ? N1 Re1 N2 C7 -3.9(4) . . . . ? Br2 Re1 N2 C7 -90.1(4) . . . . ? Br1 Re1 N2 C7 82.1(4) . . . . ? N1 C6 N3 C5 2.2(10) . . . . ? C7 C6 N3 C5 -173.3(6) . . . . ? C4 C5 N3 C6 2.4(11) . . . . ? C9 C10 N4 C7 -0.7(12) . . . . ? N2 C7 N4 C10 -0.7(11) . . . . ? C6 C7 N4 C10 175.4(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.935 _refine_diff_density_min -0.833 _refine_diff_density_rms 0.131 #==END data_3 _database_code_depnum_ccdc_archive 'CCDC 805065' #TrackingRef '3518_web_deposit_cif_file_0_Dr.OlivierBlacque_1292578226.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(4,4'-bipyridine-\kN^1^)(dibromo)dicarbonylrhenium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 Br2 N4 O2 Re' _chemical_formula_sum 'C22 H16 Br2 N4 O2 Re' _chemical_formula_weight 714.40 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.1957(16) _cell_length_b 10.5929(2) _cell_length_c 15.8194(13) _cell_angle_alpha 90.00 _cell_angle_beta 137.672(15) _cell_angle_gamma 90.00 _cell_volume 2278.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 10089 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 32.70 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1348 _exptl_absorpt_coefficient_mu 8.865 _exptl_absorpt_correction_T_min 0.829 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby Oxford Diffraction (2007). Oxford Diffraction Ltd., Xcalibur CCD system ; _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 19803 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 30.51 _reflns_number_total 3487 _reflns_number_gt 2968 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 ; _computing_structure_solution ; SHELXS97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_structure_refinement ; SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_molecular_graphics ; ORTEP-3 for Windows, Version 2.01. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. ; _computing_publication_material ; WinGX -- An integrated system of Windows programs for the solution, refinement and analysis of single crystal X-ray diffraction data, Version 1.70.01. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. PLATON for Windows, Version 1.12. Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. ; _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 'w=1/[\s^2^(Fo^2^)+(0.0202P)^2^] 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 3487 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0219 _refine_ls_wR_factor_ref 0.0425 _refine_ls_wR_factor_gt 0.0416 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 0.0000 0.476058(13) 0.7500 0.01958(4) Uani 1 2 d S . . Br1 Br 0.153583(19) 0.49263(2) 0.80766(3) 0.03222(7) Uani 1 1 d . . . C1 C 0.0563(2) 0.3411(3) 0.8676(3) 0.0327(6) Uani 1 1 d . . . C2 C 0.05962(18) 0.6058(2) 0.9731(2) 0.0268(5) Uani 1 1 d . . . H2 H 0.0383 0.5277 0.9726 0.032 Uiso 1 1 calc R . . C3 C 0.08714(18) 0.6941(2) 1.0570(2) 0.0269(6) Uani 1 1 d . . . H3 H 0.0850 0.6749 1.1123 0.032 Uiso 1 1 calc R . . C4 C 0.11836(17) 0.8126(2) 1.0604(2) 0.0219(5) Uani 1 1 d . . . C5 C 0.12392(17) 0.8318(2) 0.9784(2) 0.0239(5) Uani 1 1 d . . . H5 H 0.1459 0.9087 0.9780 0.029 Uiso 1 1 calc R . . C6 C 0.09687(17) 0.7366(2) 0.8981(2) 0.0232(5) Uani 1 1 d . . . H6 H 0.1034 0.7506 0.8466 0.028 Uiso 1 1 calc R . . C7 C 0.1472(2) 1.1254(3) 1.1981(3) 0.0386(7) Uani 1 1 d . . . H7 H 0.1360 1.2102 1.1756 0.046 Uiso 1 1 calc R . . C8 C 0.12844(19) 1.0385(2) 1.1169(3) 0.0307(6) Uani 1 1 d . . . H8 H 0.1062 1.0653 1.0433 0.037 Uiso 1 1 calc R . . C9 C 0.14321(17) 0.9112(2) 1.1468(2) 0.0252(5) Uani 1 1 d . . . C10 C 0.1797(2) 0.8790(3) 1.2609(2) 0.0349(6) Uani 1 1 d . . . H10 H 0.1928 0.7952 1.2866 0.042 Uiso 1 1 calc R . . C11 C 0.1962(2) 0.9734(3) 1.3353(3) 0.0425(7) Uani 1 1 d . . . H11 H 0.2200 0.9499 1.4106 0.051 Uiso 1 1 calc R . . N1 N 0.06149(14) 0.62489(18) 0.89082(18) 0.0215(4) Uani 1 1 d . . . N2 N 0.18010(17) 1.0961(2) 1.3059(2) 0.0418(6) Uani 1 1 d . . . O1 O 0.08964(17) 0.2572(2) 0.9345(2) 0.0579(7) 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 0.02351(7) 0.01817(7) 0.01940(7) 0.000 0.01659(6) 0.000 Br1 0.02848(14) 0.04070(17) 0.03148(15) -0.00596(11) 0.02339(13) -0.00178(10) C1 0.0355(15) 0.0289(14) 0.0352(16) 0.0021(13) 0.0267(14) 0.0008(12) C2 0.0405(15) 0.0233(12) 0.0302(14) -0.0023(11) 0.0303(13) -0.0072(11) C3 0.0386(15) 0.0275(13) 0.0271(14) -0.0012(11) 0.0281(13) -0.0041(11) C4 0.0234(12) 0.0235(12) 0.0180(12) -0.0003(10) 0.0151(11) 0.0006(10) C5 0.0272(13) 0.0229(12) 0.0221(13) -0.0002(10) 0.0184(12) -0.0042(10) C6 0.0271(13) 0.0267(13) 0.0214(13) 0.0008(10) 0.0196(12) -0.0036(10) C7 0.0383(16) 0.0291(15) 0.0444(19) -0.0081(13) 0.0293(16) -0.0005(12) C8 0.0320(14) 0.0296(15) 0.0283(14) -0.0017(12) 0.0217(12) -0.0011(12) C9 0.0243(12) 0.0279(14) 0.0231(13) -0.0028(11) 0.0174(11) -0.0006(10) C10 0.0445(17) 0.0325(15) 0.0264(15) -0.0022(12) 0.0258(14) 0.0025(12) C11 0.0512(19) 0.0484(18) 0.0300(15) -0.0054(15) 0.0306(16) -0.0013(16) N1 0.0275(11) 0.0231(11) 0.0186(10) -0.0016(8) 0.0185(10) -0.0028(8) N2 0.0425(14) 0.0425(15) 0.0399(15) -0.0149(12) 0.0303(13) -0.0037(12) O1 0.0690(16) 0.0411(13) 0.0550(15) 0.0270(12) 0.0432(14) 0.0160(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 C1 1.916(3) 2_556 ? Re1 C1 1.916(3) . ? Re1 N1 2.2135(19) . ? Re1 N1 2.2135(19) 2_556 ? Re1 Br1 2.5100(4) . ? Re1 Br1 2.5100(4) 2_556 ? C1 O1 1.144(3) . ? C2 N1 1.344(3) . ? C2 C3 1.363(3) . ? C2 H2 0.9300 . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.396(3) . ? C4 C9 1.482(3) . ? C5 C6 1.379(3) . ? C5 H5 0.9300 . ? C6 N1 1.343(3) . ? C6 H6 0.9300 . ? C7 N2 1.331(4) . ? C7 C8 1.386(4) . ? C7 H7 0.9300 . ? C8 C9 1.387(3) . ? C8 H8 0.9300 . ? C9 C10 1.397(3) . ? C10 C11 1.384(4) . ? C10 H10 0.9300 . ? C11 N2 1.338(4) . ? C11 H11 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 C1 83.47(16) 2_556 . ? C1 Re1 N1 175.90(9) 2_556 . ? C1 Re1 N1 93.76(10) . . ? C1 Re1 N1 93.76(10) 2_556 2_556 ? C1 Re1 N1 175.90(9) . 2_556 ? N1 Re1 N1 89.17(10) . 2_556 ? C1 Re1 Br1 95.26(8) 2_556 . ? C1 Re1 Br1 90.73(8) . . ? N1 Re1 Br1 87.78(5) . . ? N1 Re1 Br1 86.51(5) 2_556 . ? C1 Re1 Br1 90.73(8) 2_556 2_556 ? C1 Re1 Br1 95.26(8) . 2_556 ? N1 Re1 Br1 86.51(5) . 2_556 ? N1 Re1 Br1 87.78(5) 2_556 2_556 ? Br1 Re1 Br1 171.980(13) . 2_556 ? O1 C1 Re1 177.0(3) . . ? N1 C2 C3 123.8(2) . . ? N1 C2 H2 118.1 . . ? C3 C2 H2 118.1 . . ? C2 C3 C4 120.3(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C5 116.2(2) . . ? C3 C4 C9 120.5(2) . . ? C5 C4 C9 123.3(2) . . ? C6 C5 C4 120.0(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? N1 C6 C5 123.2(2) . . ? N1 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? N2 C7 C8 124.6(3) . . ? N2 C7 H7 117.7 . . ? C8 C7 H7 117.7 . . ? C7 C8 C9 119.2(2) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C10 116.9(2) . . ? C8 C9 C4 122.0(2) . . ? C10 C9 C4 121.1(2) . . ? C11 C10 C9 119.2(3) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? N2 C11 C10 124.2(3) . . ? N2 C11 H11 117.9 . . ? C10 C11 H11 117.9 . . ? C6 N1 C2 116.3(2) . . ? C6 N1 Re1 125.56(15) . . ? C2 N1 Re1 118.05(15) . . ? C7 N2 C11 115.8(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 N1 C2 C3 C4 0.8(4) . . . . ? C2 C3 C4 C5 -3.0(4) . . . . ? C2 C3 C4 C9 176.7(2) . . . . ? C3 C4 C5 C6 1.5(3) . . . . ? C9 C4 C5 C6 -178.1(2) . . . . ? C4 C5 C6 N1 2.3(4) . . . . ? N2 C7 C8 C9 0.8(4) . . . . ? C7 C8 C9 C10 -2.0(4) . . . . ? C7 C8 C9 C4 175.8(2) . . . . ? C3 C4 C9 C8 -148.1(2) . . . . ? C5 C4 C9 C8 31.5(4) . . . . ? C3 C4 C9 C10 29.7(4) . . . . ? C5 C4 C9 C10 -150.7(3) . . . . ? C8 C9 C10 C11 1.9(4) . . . . ? C4 C9 C10 C11 -176.0(2) . . . . ? C9 C10 C11 N2 -0.5(5) . . . . ? C5 C6 N1 C2 -4.4(4) . . . . ? C5 C6 N1 Re1 172.31(18) . . . . ? C3 C2 N1 C6 2.9(4) . . . . ? C3 C2 N1 Re1 -174.1(2) . . . . ? C1 Re1 N1 C6 142.1(2) . . . . ? N1 Re1 N1 C6 -35.06(16) 2_556 . . . ? Br1 Re1 N1 C6 51.48(19) . . . . ? Br1 Re1 N1 C6 -122.89(19) 2_556 . . . ? C1 Re1 N1 C2 -41.3(2) . . . . ? N1 Re1 N1 C2 141.6(2) 2_556 . . . ? Br1 Re1 N1 C2 -131.84(18) . . . . ? Br1 Re1 N1 C2 53.79(18) 2_556 . . . ? C8 C7 N2 C11 0.7(4) . . . . ? C10 C11 N2 C7 -0.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.843 _refine_diff_density_min -1.026 _refine_diff_density_rms 0.109 #==END data_6 _database_code_depnum_ccdc_archive 'CCDC 805066' #TrackingRef '3518_web_deposit_cif_file_0_Dr.OlivierBlacque_1292578226.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ;\ Tetraethylammonium hexabromo(tetracarbonyl)(\m-pyrazine-\kN^1^:\kN^4^)\ dirhenium(II) (2/1) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 N, 0.5(C8 H4 Br6 N2 O4 Re2)' _chemical_formula_sum 'C12 H22 Br3 N2 O2 Re' _chemical_formula_weight 652.23 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.7206(3) _cell_length_b 17.3868(10) _cell_length_c 13.9806(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.836(4) _cell_angle_gamma 90.00 _cell_volume 1859.18(15) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 278 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 32.65 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 12.985 _exptl_absorpt_correction_T_min 0.86519 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby Oxford Diffraction (2007). Oxford Diffraction Ltd., Xcalibur CCD system ; _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 17424 _diffrn_reflns_av_R_equivalents 0.0983 _diffrn_reflns_av_sigmaI/netI 0.1461 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3533 _reflns_number_gt 2023 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 ; _computing_structure_solution ; SHELXS97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_structure_refinement ; SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_molecular_graphics ; ORTEP-3 for Windows, Version 2.01. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. ; _computing_publication_material ; WinGX -- An integrated system of Windows programs for the solution, refinement and analysis of single crystal X-ray diffraction data, Version 1.70.01. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. PLATON for Windows, Version 1.12. Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. ; _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 'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^] 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 3533 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 0.816 _refine_ls_restrained_S_all 0.816 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.37103(6) -0.00738(3) 0.73881(4) 0.02045(16) Uani 1 1 d . . . Br2 Br 0.32343(18) -0.14961(8) 0.70269(10) 0.0355(4) Uani 1 1 d . . . Br3 Br 0.45425(18) 0.13349(8) 0.75646(10) 0.0344(4) Uani 1 1 d . . . Br1 Br 0.06087(16) 0.03033(9) 0.66092(10) 0.0384(4) Uani 1 1 d . . . C2 C 0.6121(18) -0.0344(7) 0.8008(9) 0.020(3) Uani 1 1 d . . . C1 C 0.2998(18) -0.0181(8) 0.8633(9) 0.033(3) Uani 1 1 d . . . C3 C 0.3476(15) -0.0323(7) 0.5151(9) 0.021(3) Uani 1 1 d . . . H3 H 0.2411 -0.0548 0.5230 0.025 Uiso 1 1 calc R . . C4 C 0.5965(14) 0.0319(7) 0.5746(8) 0.019(3) Uani 1 1 d . . . H4 H 0.6667 0.0552 0.6258 0.023 Uiso 1 1 calc R . . C11 C 0.2990(17) 0.2316(9) 1.0559(9) 0.042(4) Uani 1 1 d . . . H11A H 0.3225 0.2836 1.0792 0.050 Uiso 1 1 calc R . . H11B H 0.2791 0.2004 1.1108 0.050 Uiso 1 1 calc R . . C12 C 0.4589(17) 0.2021(11) 1.0185(11) 0.059(5) Uani 1 1 d . . . H12A H 0.4812 0.2326 0.9642 0.089 Uiso 1 1 calc R . . H12B H 0.4409 0.1495 0.9988 0.089 Uiso 1 1 calc R . . H12C H 0.5571 0.2053 1.0684 0.089 Uiso 1 1 calc R . . C7 C 0.0770(19) 0.1517(8) 0.9567(11) 0.047(4) Uani 1 1 d . . . H7A H 0.0717 0.1225 1.0154 0.057 Uiso 1 1 calc R . . H7B H 0.1679 0.1289 0.9243 0.057 Uiso 1 1 calc R . . C9 C 0.1577(17) 0.2730(8) 0.8932(10) 0.035(4) Uani 1 1 d . . . H9A H 0.2376 0.2427 0.8606 0.042 Uiso 1 1 calc R . . H9B H 0.0468 0.2750 0.8512 0.042 Uiso 1 1 calc R . . C5 C -0.0117(17) 0.2720(8) 1.0299(10) 0.041(4) Uani 1 1 d . . . H5A H 0.0235 0.3248 1.0438 0.049 Uiso 1 1 calc R . . H5B H -0.1163 0.2733 0.9828 0.049 Uiso 1 1 calc R . . C6 C -0.058(2) 0.2364(10) 1.1208(11) 0.065(5) Uani 1 1 d . . . H6A H 0.0445 0.2344 1.1682 0.098 Uiso 1 1 calc R . . H6B H -0.1010 0.1852 1.1074 0.098 Uiso 1 1 calc R . . H6C H -0.1460 0.2668 1.1450 0.098 Uiso 1 1 calc R . . C8 C -0.0953(19) 0.1421(9) 0.8923(11) 0.053(4) Uani 1 1 d . . . H8A H -0.0915 0.1693 0.8328 0.079 Uiso 1 1 calc R . . H8B H -0.1879 0.1625 0.9242 0.079 Uiso 1 1 calc R . . H8C H -0.1162 0.0885 0.8789 0.079 Uiso 1 1 calc R . . C10 C 0.2267(19) 0.3512(9) 0.9061(11) 0.055(5) Uani 1 1 d . . . H10A H 0.3372 0.3501 0.9470 0.082 Uiso 1 1 calc R . . H10B H 0.1461 0.3825 0.9355 0.082 Uiso 1 1 calc R . . H10C H 0.2422 0.3724 0.8445 0.082 Uiso 1 1 calc R . . N1 N 0.4478(11) -0.0001(6) 0.5913(6) 0.017(2) Uani 1 1 d . . . N2 N 0.1306(12) 0.2328(6) 0.9845(7) 0.023(2) Uani 1 1 d . . . O2 O 0.7358(13) -0.0499(5) 0.8371(7) 0.039(3) Uani 1 1 d . . . O1 O 0.2610(14) -0.0251(6) 0.9384(7) 0.055(3) 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 0.0237(2) 0.0220(3) 0.0163(2) 0.0013(3) 0.00494(19) 0.0015(3) Br2 0.0467(9) 0.0285(9) 0.0321(8) -0.0002(7) 0.0085(7) -0.0099(6) Br3 0.0470(9) 0.0262(9) 0.0294(8) -0.0021(6) 0.0031(7) 0.0031(6) Br1 0.0204(7) 0.0584(11) 0.0370(8) 0.0036(7) 0.0065(6) 0.0059(7) C2 0.028(8) 0.016(7) 0.019(7) 0.003(6) 0.009(6) 0.001(6) C1 0.052(9) 0.030(9) 0.017(7) -0.004(6) 0.009(7) 0.004(7) C3 0.015(6) 0.024(8) 0.024(7) 0.002(6) 0.002(6) 0.003(5) C4 0.011(6) 0.031(8) 0.015(6) -0.008(6) -0.001(5) -0.008(5) C11 0.048(9) 0.056(11) 0.016(8) -0.007(7) -0.014(7) -0.011(8) C12 0.029(9) 0.090(15) 0.055(12) -0.007(10) -0.011(8) 0.020(8) C7 0.061(11) 0.017(9) 0.061(11) 0.002(8) -0.003(9) -0.006(7) C9 0.032(8) 0.025(9) 0.049(10) 0.004(7) 0.010(7) 0.008(6) C5 0.040(9) 0.035(10) 0.049(10) -0.002(8) 0.009(8) -0.001(7) C6 0.067(12) 0.096(16) 0.039(10) 0.006(10) 0.027(9) -0.013(10) C8 0.059(11) 0.048(11) 0.045(10) -0.003(8) -0.012(9) -0.020(8) C10 0.049(10) 0.058(13) 0.061(12) 0.026(9) 0.019(9) 0.003(8) N1 0.022(5) 0.017(6) 0.013(5) 0.001(5) 0.002(4) -0.003(5) N2 0.032(6) 0.020(7) 0.015(6) 0.001(5) -0.002(5) -0.004(5) O2 0.039(6) 0.033(6) 0.044(7) 0.005(5) -0.001(5) 0.004(5) O1 0.090(8) 0.053(8) 0.028(6) 0.009(5) 0.030(6) 0.014(6) _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 1.905(12) . ? Re1 C2 1.999(14) . ? Re1 N1 2.226(8) . ? Re1 Br3 2.5355(15) . ? Re1 Br2 2.5408(15) . ? Re1 Br1 2.5766(14) . ? C2 O2 1.054(13) . ? C1 O1 1.136(14) . ? C3 N1 1.350(14) . ? C3 C4 1.380(15) 3_656 ? C3 H3 0.9300 . ? C4 N1 1.325(13) . ? C4 C3 1.380(15) 3_656 ? C4 H4 0.9300 . ? C11 C12 1.496(17) . ? C11 N2 1.527(14) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C7 N2 1.506(15) . ? C7 C8 1.510(18) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C10 1.464(18) . ? C9 N2 1.495(15) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C5 C6 1.499(18) . ? C5 N2 1.505(15) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 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 C1 Re1 C2 87.0(5) . . ? C1 Re1 N1 177.3(5) . . ? C2 Re1 N1 93.8(4) . . ? C1 Re1 Br3 96.1(4) . . ? C2 Re1 Br3 88.6(4) . . ? N1 Re1 Br3 86.5(3) . . ? C1 Re1 Br2 92.0(4) . . ? C2 Re1 Br2 87.6(4) . . ? N1 Re1 Br2 85.4(3) . . ? Br3 Re1 Br2 170.90(5) . . ? C1 Re1 Br1 92.5(4) . . ? C2 Re1 Br1 178.7(4) . . ? N1 Re1 Br1 86.8(2) . . ? Br3 Re1 Br1 90.23(5) . . ? Br2 Re1 Br1 93.60(5) . . ? O2 C2 Re1 176.6(12) . . ? O1 C1 Re1 178.4(13) . . ? N1 C3 C4 119.9(10) . 3_656 ? N1 C3 H3 120.1 . . ? C4 C3 H3 120.1 3_656 . ? N1 C4 C3 123.2(11) . 3_656 ? N1 C4 H4 118.4 . . ? C3 C4 H4 118.4 3_656 . ? C12 C11 N2 116.4(10) . . ? C12 C11 H11A 108.2 . . ? N2 C11 H11A 108.2 . . ? C12 C11 H11B 108.2 . . ? N2 C11 H11B 108.2 . . ? H11A C11 H11B 107.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C7 C8 116.5(11) . . ? N2 C7 H7A 108.2 . . ? C8 C7 H7A 108.2 . . ? N2 C7 H7B 108.2 . . ? C8 C7 H7B 108.2 . . ? H7A C7 H7B 107.3 . . ? C10 C9 N2 114.8(12) . . ? C10 C9 H9A 108.6 . . ? N2 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? N2 C9 H9B 108.6 . . ? H9A C9 H9B 107.5 . . ? C6 C5 N2 116.2(12) . . ? C6 C5 H5A 108.2 . . ? N2 C5 H5A 108.2 . . ? C6 C5 H5B 108.2 . . ? N2 C5 H5B 108.2 . . ? H5A C5 H5B 107.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C4 N1 C3 116.9(9) . . ? C4 N1 Re1 122.2(7) . . ? C3 N1 Re1 120.8(7) . . ? C9 N2 C5 110.1(10) . . ? C9 N2 C7 106.4(10) . . ? C5 N2 C7 110.0(10) . . ? C9 N2 C11 111.0(10) . . ? C5 N2 C11 109.6(9) . . ? C7 N2 C11 109.7(10) . . ? 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 C4 N1 C3 -1.1(19) 3_656 . . . ? C3 C4 N1 Re1 175.4(9) 3_656 . . . ? C4 C3 N1 C4 1.1(19) 3_656 . . . ? C4 C3 N1 Re1 -175.5(8) 3_656 . . . ? C2 Re1 N1 C4 -40.9(10) . . . . ? Br3 Re1 N1 C4 47.5(9) . . . . ? Br2 Re1 N1 C4 -128.2(9) . . . . ? Br1 Re1 N1 C4 137.9(9) . . . . ? C2 Re1 N1 C3 135.4(9) . . . . ? Br3 Re1 N1 C3 -136.1(9) . . . . ? Br2 Re1 N1 C3 48.1(8) . . . . ? Br1 Re1 N1 C3 -45.7(8) . . . . ? C10 C9 N2 C5 66.3(14) . . . . ? C10 C9 N2 C7 -174.5(12) . . . . ? C10 C9 N2 C11 -55.2(14) . . . . ? C6 C5 N2 C9 178.1(12) . . . . ? C6 C5 N2 C7 61.1(15) . . . . ? C6 C5 N2 C11 -59.6(16) . . . . ? C8 C7 N2 C9 -64.5(15) . . . . ? C8 C7 N2 C5 54.7(16) . . . . ? C8 C7 N2 C11 175.3(12) . . . . ? C12 C11 N2 C9 -51.9(16) . . . . ? C12 C11 N2 C5 -173.7(13) . . . . ? C12 C11 N2 C7 65.4(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.909 _refine_diff_density_min -1.473 _refine_diff_density_rms 0.288 #==END data_9 _database_code_depnum_ccdc_archive 'CCDC 805067' #TrackingRef '3518_web_deposit_cif_file_0_Dr.OlivierBlacque_1292578226.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetraethylammonium tribromo(dicarbonyl)(pyridazine-\kN^1^)rhenium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 N, C6 H4 Br2 Cl N2 O2 Re' _chemical_formula_sum 'C14 H24 Br2 Cl N3 O2 Re' _chemical_formula_weight 647.82 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.1336(3) _cell_length_b 8.2350(1) _cell_length_c 17.0551(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.105(2) _cell_angle_gamma 90.00 _cell_volume 2068.35(7) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 14900 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 32.76 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.080 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 9.878 _exptl_absorpt_correction_T_min 0.105 _exptl_absorpt_correction_T_max 0.783 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55. Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby Oxford Diffraction (2007). Oxford Diffraction Ltd., Xcalibur CCD system ; _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 37577 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 29.13 _reflns_number_total 5571 _reflns_number_gt 3839 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_structure_solution ; SHELXS97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_structure_refinement ; SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_molecular_graphics ; ORTEP-3 for Windows, Version 2.01. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. ; _computing_publication_material ; WinGX -- An integrated system of Windows programs for the solution, refinement and analysis of single crystal X-ray diffraction data, Version 1.70.01. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. PLATON for Windows, Version 1.12. Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. ; _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 'w=1/[\s^2^(Fo^2^)+(0.0464P)^2^] 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 5571 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.002 _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 C1 C 0.7719(4) 0.1071(7) -0.0443(4) 0.0364(16) Uani 1 1 d . . . C2 C 0.6278(5) 0.2924(7) -0.1011(5) 0.0376(15) Uani 1 1 d . . . C3 C 0.7075(4) 0.4826(7) 0.1531(4) 0.0373(15) Uani 1 1 d . . . H3 H 0.7527 0.4132 0.1886 0.045 Uiso 1 1 calc R . . C4 C 0.6715(5) 0.5959(7) 0.1903(4) 0.0391(16) Uani 1 1 d . . . H4 H 0.6907 0.6018 0.2496 0.047 Uiso 1 1 calc R . . C5 C 0.6082(5) 0.6968(7) 0.1379(4) 0.0392(16) Uani 1 1 d . . . H5 H 0.5824 0.7766 0.1593 0.047 Uiso 1 1 calc R . . C6 C 0.5827(5) 0.6781(7) 0.0508(4) 0.0418(18) Uani 1 1 d . . . H6 H 0.5384 0.7480 0.0145 0.050 Uiso 1 1 calc R . . C7 C 0.5492(5) 0.8851(7) -0.2378(4) 0.0397(16) Uani 1 1 d . . . H7A H 0.5992 0.9554 -0.2331 0.048 Uiso 1 1 calc R . . H7B H 0.4944 0.9504 -0.2589 0.048 Uiso 1 1 calc R . . C8 C 0.5658(6) 0.8220(9) -0.1481(5) 0.058(2) Uani 1 1 d . . . H8A H 0.6209 0.7599 -0.1257 0.087 Uiso 1 1 calc R . . H8B H 0.5159 0.7544 -0.1516 0.087 Uiso 1 1 calc R . . H8C H 0.5709 0.9122 -0.1107 0.087 Uiso 1 1 calc R . . C9 C 0.6230(4) 0.6517(7) -0.2757(4) 0.0370(15) Uani 1 1 d . . . H9A H 0.6141 0.5708 -0.3198 0.044 Uiso 1 1 calc R . . H9B H 0.6290 0.5940 -0.2241 0.044 Uiso 1 1 calc R . . C10 C 0.7108(5) 0.7349(8) -0.2577(4) 0.0445(18) Uani 1 1 d . . . H10A H 0.7217 0.8152 -0.2138 0.067 Uiso 1 1 calc R . . H10B H 0.7084 0.7864 -0.3090 0.067 Uiso 1 1 calc R . . H10C H 0.7591 0.6566 -0.2385 0.067 Uiso 1 1 calc R . . C11 C 0.5200(4) 0.8426(7) -0.3875(3) 0.0355(15) Uani 1 1 d . . . H11A H 0.4673 0.9112 -0.4002 0.043 Uiso 1 1 calc R . . H11B H 0.5712 0.9130 -0.3792 0.043 Uiso 1 1 calc R . . C12 C 0.5032(5) 0.7350(8) -0.4641(4) 0.0471(18) Uani 1 1 d . . . H12A H 0.4509 0.6684 -0.4748 0.071 Uiso 1 1 calc R . . H12B H 0.5552 0.6671 -0.4527 0.071 Uiso 1 1 calc R . . H12C H 0.4928 0.8012 -0.5136 0.071 Uiso 1 1 calc R . . C13 C 0.4611(4) 0.6403(8) -0.3140(4) 0.0434(17) Uani 1 1 d . . . H13A H 0.4563 0.5589 -0.3568 0.052 Uiso 1 1 calc R . . H13B H 0.4756 0.5840 -0.2600 0.052 Uiso 1 1 calc R . . C14 C 0.3708(5) 0.7184(8) -0.3394(5) 0.058(2) Uani 1 1 d . . . H14A H 0.3729 0.7936 -0.2957 0.087 Uiso 1 1 calc R . . H14B H 0.3259 0.6367 -0.3464 0.087 Uiso 1 1 calc R . . H14C H 0.3553 0.7752 -0.3927 0.087 Uiso 1 1 calc R . . N1 N 0.6800(3) 0.4692(5) 0.0688(3) 0.0261(11) Uani 1 1 d . . . N2 N 0.6160(4) 0.5690(6) 0.0147(3) 0.0384(13) Uani 1 1 d . . . N3 N 0.5394(4) 0.7519(5) -0.3037(3) 0.0315(12) Uani 1 1 d . . . O1 O 0.7923(3) 0.0040(5) -0.0730(3) 0.0478(13) Uani 1 1 d . . . O2 O 0.5728(3) 0.2957(6) -0.1636(3) 0.0507(13) Uani 1 1 d . . . Br1 Br 0.88095(6) 0.27683(10) 0.14164(5) 0.0323(2) Uani 0.50 1 d P . . Cl1 Cl 0.88095(6) 0.27683(10) 0.14164(5) 0.0323(2) Uani 0.50 1 d P . . Br2 Br 0.79387(6) 0.51099(10) -0.05038(5) 0.0363(2) Uani 0.50 1 d P . . Cl2 Cl 0.79387(6) 0.51099(10) -0.05038(5) 0.0363(2) Uani 0.50 1 d P . . Br3 Br 0.65455(5) 0.08942(8) 0.07341(4) 0.04585(19) Uani 1 1 d . . . Re1 Re 0.731845(16) 0.28194(3) 0.007351(14) 0.02611(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 C1 0.045(4) 0.031(3) 0.024(3) 0.002(2) 0.005(3) -0.007(3) C2 0.051(4) 0.027(3) 0.055(4) 0.001(3) 0.042(4) -0.008(3) C3 0.041(4) 0.044(4) 0.025(3) 0.006(3) 0.011(3) 0.003(3) C4 0.054(4) 0.035(3) 0.027(3) -0.005(3) 0.016(3) -0.002(3) C5 0.049(4) 0.032(3) 0.055(4) -0.011(3) 0.040(3) -0.004(3) C6 0.048(4) 0.026(3) 0.046(4) 0.002(3) 0.015(3) 0.008(3) C7 0.043(4) 0.032(3) 0.045(4) 0.000(3) 0.019(3) -0.002(3) C8 0.066(6) 0.070(5) 0.043(4) 0.001(4) 0.028(4) -0.006(4) C9 0.042(4) 0.026(3) 0.042(4) 0.005(3) 0.017(3) 0.005(3) C10 0.040(4) 0.052(4) 0.038(4) 0.005(3) 0.011(3) 0.003(3) C11 0.035(4) 0.038(3) 0.031(3) 0.009(3) 0.012(3) -0.001(3) C12 0.046(4) 0.057(4) 0.038(4) -0.002(3) 0.017(3) 0.005(3) C13 0.039(4) 0.037(4) 0.059(4) 0.001(3) 0.024(3) -0.009(3) C14 0.044(5) 0.051(4) 0.079(6) 0.008(4) 0.025(4) -0.007(4) N1 0.032(3) 0.022(2) 0.025(2) 0.0031(18) 0.013(2) -0.0006(19) N2 0.040(3) 0.036(3) 0.035(3) 0.006(2) 0.010(2) 0.010(2) N3 0.036(3) 0.024(2) 0.037(3) 0.0051(19) 0.016(2) 0.0019(19) O1 0.050(3) 0.036(3) 0.055(3) -0.003(2) 0.019(2) 0.007(2) O2 0.041(3) 0.057(3) 0.044(3) 0.003(2) 0.007(2) -0.006(2) Br1 0.0334(5) 0.0302(4) 0.0271(4) 0.0036(3) 0.0061(3) -0.0018(4) Cl1 0.0334(5) 0.0302(4) 0.0271(4) 0.0036(3) 0.0061(3) -0.0018(4) Br2 0.0368(5) 0.0366(4) 0.0312(4) -0.0010(3) 0.0094(4) 0.0011(4) Cl2 0.0368(5) 0.0366(4) 0.0312(4) -0.0010(3) 0.0094(4) 0.0011(4) Br3 0.0454(4) 0.0391(4) 0.0503(4) 0.0055(3) 0.0168(3) -0.0060(3) Re1 0.02653(13) 0.02531(11) 0.02430(12) -0.00090(10) 0.00816(9) -0.00047(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.096(7) . ? C1 Re1 1.931(7) . ? C2 O2 1.073(7) . ? C2 Re1 1.927(7) . ? C3 N1 1.325(7) . ? C3 C4 1.382(9) . ? C3 H3 0.9300 . ? C4 C5 1.336(8) . ? C4 H4 0.9300 . ? C5 C6 1.378(9) . ? C5 H5 0.9300 . ? C6 N2 1.320(8) . ? C6 H6 0.9300 . ? C7 C8 1.532(9) . ? C7 N3 1.532(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N3 1.484(8) . ? C9 C10 1.488(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.508(8) . ? C11 N3 1.528(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.486(9) . ? C13 N3 1.514(8) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? N1 N2 1.347(6) . ? N1 Re1 2.212(5) . ? Br1 Re1 2.5562(8) . ? Br2 Re1 2.5166(10) . ? Br3 Re1 2.5467(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 O1 C1 Re1 177.2(6) . . ? O2 C2 Re1 176.0(6) . . ? N1 C3 C4 122.5(5) . . ? N1 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C5 C4 C3 117.5(6) . . ? C5 C4 H4 121.3 . . ? C3 C4 H4 121.3 . . ? C4 C5 C6 117.5(6) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? N2 C6 C5 125.4(6) . . ? N2 C6 H6 117.3 . . ? C5 C6 H6 117.3 . . ? C8 C7 N3 114.4(5) . . ? C8 C7 H7A 108.7 . . ? N3 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? N3 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 C10 118.3(5) . . ? N3 C9 H9A 107.7 . . ? C10 C9 H9A 107.7 . . ? N3 C9 H9B 107.7 . . ? C10 C9 H9B 107.7 . . ? H9A C9 H9B 107.1 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 N3 114.7(5) . . ? C12 C11 H11A 108.6 . . ? N3 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? N3 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 N3 116.3(5) . . ? C14 C13 H13A 108.2 . . ? N3 C13 H13A 108.2 . . ? C14 C13 H13B 108.2 . . ? N3 C13 H13B 108.2 . . ? H13A C13 H13B 107.4 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3 N1 N2 121.0(5) . . ? C3 N1 Re1 123.3(4) . . ? N2 N1 Re1 115.7(3) . . ? C6 N2 N1 116.1(5) . . ? C9 N3 C13 107.8(4) . . ? C9 N3 C11 112.6(5) . . ? C13 N3 C11 110.2(5) . . ? C9 N3 C7 110.8(5) . . ? C13 N3 C7 110.5(5) . . ? C11 N3 C7 104.9(4) . . ? C2 Re1 C1 85.3(2) . . ? C2 Re1 N1 94.2(2) . . ? C1 Re1 N1 175.9(2) . . ? C2 Re1 Br2 85.47(17) . . ? C1 Re1 Br2 96.87(19) . . ? N1 Re1 Br2 87.16(12) . . ? C2 Re1 Br3 93.45(18) . . ? C1 Re1 Br3 93.05(19) . . ? N1 Re1 Br3 82.89(12) . . ? Br2 Re1 Br3 169.89(3) . . ? C2 Re1 Br1 173.37(19) . . ? C1 Re1 Br1 91.63(16) . . ? N1 Re1 Br1 89.24(11) . . ? Br2 Re1 Br1 89.07(3) . . ? Br3 Re1 Br1 92.58(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 N1 C3 C4 C5 -1.6(10) . . . . ? C3 C4 C5 C6 1.1(10) . . . . ? C4 C5 C6 N2 -0.4(11) . . . . ? C4 C3 N1 N2 1.3(9) . . . . ? C4 C3 N1 Re1 -177.1(5) . . . . ? C5 C6 N2 N1 0.1(10) . . . . ? C3 N1 N2 C6 -0.5(8) . . . . ? Re1 N1 N2 C6 178.1(5) . . . . ? C10 C9 N3 C13 -177.6(6) . . . . ? C10 C9 N3 C11 60.5(7) . . . . ? C10 C9 N3 C7 -56.6(7) . . . . ? C14 C13 N3 C9 178.2(6) . . . . ? C14 C13 N3 C11 -58.4(8) . . . . ? C14 C13 N3 C7 57.0(7) . . . . ? C12 C11 N3 C9 62.2(7) . . . . ? C12 C11 N3 C13 -58.3(7) . . . . ? C12 C11 N3 C7 -177.2(6) . . . . ? C8 C7 N3 C9 -60.3(7) . . . . ? C8 C7 N3 C13 59.1(7) . . . . ? C8 C7 N3 C11 177.9(6) . . . . ? C3 N1 Re1 C2 157.8(5) . . . . ? N2 N1 Re1 C2 -20.8(4) . . . . ? C3 N1 Re1 Br2 -117.0(5) . . . . ? N2 N1 Re1 Br2 64.5(4) . . . . ? C3 N1 Re1 Br3 64.8(5) . . . . ? N2 N1 Re1 Br3 -113.7(4) . . . . ? C3 N1 Re1 Br1 -27.9(5) . . . . ? N2 N1 Re1 Br1 153.6(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.512 _refine_diff_density_min -1.243 _refine_diff_density_rms 0.165 #==END data_10 _database_code_depnum_ccdc_archive 'CCDC 805068' #TrackingRef '3518_web_deposit_cif_file_0_Dr.OlivierBlacque_1292578226.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bromo(dicarbonyl)tris(pyridazine-\kN^1^)rhenium(II) dichloromethane solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 Br N6 O2 Re, C H2 Cl2' _chemical_formula_sum 'C15 H14 Br Cl2 N6 O2 Re' _chemical_formula_weight 647.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.1131(6) _cell_length_b 8.5890(6) _cell_length_c 28.428(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.886(7) _cell_angle_gamma 90.00 _cell_volume 1979.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 3560 _cell_measurement_theta_min 2.4723 _cell_measurement_theta_max 32.7569 _exptl_crystal_description 'tiny plate' _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.025 _exptl_crystal_size_min 0.010 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 8.449 _exptl_absorpt_correction_T_min 0.859 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby Oxford Diffraction (2007). Oxford Diffraction Ltd., Xcalibur CCD system ; _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 19970 _diffrn_reflns_av_R_equivalents 0.1149 _diffrn_reflns_av_sigmaI/netI 0.1446 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3484 _reflns_number_gt 2024 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_structure_solution ; SHELXS97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_structure_refinement ; SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_molecular_graphics ; ORTEP-3 for Windows, Version 2.01. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. ; _computing_publication_material ; WinGX -- An integrated system of Windows programs for the solution, refinement and analysis of single crystal X-ray diffraction data, Version 1.70.01. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. SHELXL97. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. PLATON for Windows, Version 1.12. Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. ; _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 'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^] 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 3484 _refine_ls_number_parameters 242 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0405 _refine_ls_wR_factor_gt 0.0364 _refine_ls_goodness_of_fit_ref 0.692 _refine_ls_restrained_S_all 0.692 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2136(9) 0.4840(8) -0.0622(3) 0.041(2) Uani 1 1 d . A . C2 C 0.7561(9) 0.4260(8) -0.1504(3) 0.042(2) Uani 1 1 d . . . H2 H 0.8098 0.3947 -0.1772 0.050 Uiso 1 1 calc R . . C3 C 0.8358(9) 0.5286(9) -0.1205(3) 0.041(2) Uani 1 1 d . . . H3 H 0.9374 0.5716 -0.1275 0.049 Uiso 1 1 calc R . . C4 C 0.7583(9) 0.5640(8) -0.0803(3) 0.050(3) Uani 1 1 d . . . H4 H 0.8064 0.6305 -0.0580 0.060 Uiso 1 1 calc R . . C5 C 0.6031(9) 0.4969(8) -0.0735(3) 0.040(2) Uani 1 1 d . . . H5 H 0.5502 0.5196 -0.0458 0.048 Uiso 1 1 calc R . . C6 C 0.3749(9) -0.1813(10) -0.1183(3) 0.057(2) Uani 1 1 d . . . H6 H 0.3552 -0.2698 -0.1005 0.069 Uiso 1 1 calc R . . C7 C 0.4337(9) -0.2031(10) -0.1618(3) 0.048(2) Uani 1 1 d . . . H7 H 0.4567 -0.3025 -0.1728 0.058 Uiso 1 1 calc R . . C8 C 0.4577(9) -0.0764(8) -0.1886(3) 0.045(2) Uani 1 1 d . . . H8 H 0.4969 -0.0852 -0.2189 0.054 Uiso 1 1 calc R . . C9 C 0.4220(8) 0.0678(8) -0.1694(3) 0.037(2) Uani 1 1 d . . . H9 H 0.4355 0.1567 -0.1876 0.044 Uiso 1 1 calc R . . C10 C -0.1376(10) 0.0221(8) -0.1107(3) 0.047(2) Uani 1 1 d . . . H10 H -0.1777 -0.0409 -0.1350 0.056 Uiso 1 1 calc R . . C11 C -0.2274(9) 0.0335(9) -0.0704(3) 0.041(2) Uani 1 1 d . . . H11 H -0.3269 -0.0188 -0.0676 0.049 Uiso 1 1 calc R . . C12 C -0.1641(9) 0.1241(8) -0.0354(3) 0.039(2) Uani 1 1 d . . . H12 H -0.2190 0.1354 -0.0074 0.047 Uiso 1 1 calc R . . C13 C -0.0159(8) 0.1997(8) -0.0420(2) 0.0331(18) Uani 1 1 d . . . H13 H 0.0286 0.2604 -0.0176 0.040 Uiso 1 1 calc R . . N1 N 0.5286(6) 0.4039(6) -0.1040(2) 0.0223(14) Uani 1 1 d . A . N2 N 0.6037(7) 0.3672(6) -0.1433(2) 0.0359(17) Uani 1 1 d . . . N3 N 0.3681(6) 0.0831(6) -0.1253(2) 0.0263(15) Uani 1 1 d . A . N4 N 0.3429(7) -0.0451(7) -0.0988(2) 0.0447(19) Uani 1 1 d . . . N5 N 0.0654(6) 0.1887(7) -0.08190(19) 0.0276(14) Uani 1 1 d . A . N6 N 0.0055(7) 0.0984(7) -0.1162(2) 0.0365(17) Uani 1 1 d . . . O1 O 0.1647(6) 0.5877(5) -0.04094(18) 0.0491(17) Uani 1 1 d . . . C2A C 0.3708(15) 0.2396(13) -0.0342(4) 0.0364(4) Uani 0.6796(14) 1 d PD A 1 O2A O 0.4349(10) 0.1979(11) 0.0055(3) 0.0364(4) Uani 0.6796(14) 1 d PD A 1 Br1A Br 0.1958(2) 0.39759(19) -0.17455(5) 0.0364(4) Uani 0.6796 1 d P A 1 C2B C 0.217(3) 0.387(3) -0.1477(6) 0.0364(4) Uani 0.3204(14) 1 d PD A 2 O2B O 0.161(3) 0.427(3) -0.1885(5) 0.0364(4) Uani 0.3204(14) 1 d PD A 2 Br1B Br 0.4045(3) 0.2011(4) -0.01498(8) 0.0364(4) Uani 0.3204(14) 1 d P A 2 Re1 Re 0.29376(4) 0.30338(3) -0.092017(11) 0.02778(9) Uani 1 1 d D . . C14 C 0.0313(9) 0.0009(8) -0.2269(3) 0.055(3) Uani 1 1 d . . . H14A H 0.1046 0.0130 -0.2529 0.066 Uiso 1 1 calc R . . H14B H 0.0837 0.0496 -0.1995 0.066 Uiso 1 1 calc R . . Cl1 Cl -0.1537(3) 0.0984(2) -0.24055(8) 0.0661(7) Uani 1 1 d . . . Cl2 Cl 0.0066(3) -0.1974(3) -0.21553(8) 0.0786(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.034(5) 0.043(6) 0.047(6) 0.004(4) 0.016(5) -0.020(4) C2 0.039(6) 0.049(6) 0.037(6) -0.005(4) 0.011(5) 0.001(4) C3 0.028(5) 0.047(6) 0.047(6) -0.002(5) 0.012(5) 0.001(4) C4 0.029(6) 0.055(6) 0.064(8) -0.009(5) -0.005(5) -0.008(5) C5 0.023(5) 0.044(5) 0.053(6) -0.003(5) 0.005(5) 0.011(4) C6 0.078(7) 0.030(5) 0.065(7) 0.010(5) 0.022(5) 0.011(6) C7 0.048(5) 0.027(5) 0.070(6) -0.008(6) 0.002(5) 0.000(5) C8 0.054(6) 0.046(6) 0.034(6) -0.026(5) 0.012(5) 0.005(5) C9 0.030(5) 0.044(5) 0.036(6) 0.004(4) 0.012(4) -0.007(4) C10 0.049(6) 0.041(6) 0.051(6) -0.003(5) -0.002(5) -0.030(5) C11 0.026(6) 0.055(6) 0.042(6) 0.005(5) 0.003(5) -0.023(4) C12 0.030(5) 0.036(5) 0.053(6) 0.004(4) 0.015(5) 0.001(4) C13 0.033(5) 0.032(4) 0.034(5) -0.006(5) 0.012(4) -0.005(5) N1 0.017(4) 0.030(4) 0.020(4) -0.007(3) 0.007(3) 0.000(3) N2 0.028(4) 0.041(4) 0.039(5) -0.005(3) 0.010(3) -0.005(3) N3 0.014(4) 0.031(4) 0.034(4) -0.002(3) 0.005(3) 0.008(3) N4 0.048(5) 0.032(4) 0.054(5) 0.007(4) 0.003(4) 0.013(3) N5 0.032(4) 0.023(3) 0.028(4) -0.002(4) 0.001(3) 0.003(4) N6 0.037(5) 0.042(4) 0.030(5) 0.002(3) 0.003(4) -0.011(3) O1 0.051(4) 0.039(4) 0.059(4) -0.026(3) 0.023(3) -0.005(3) C2A 0.0336(9) 0.0411(8) 0.0346(11) 0.0052(8) 0.0045(8) 0.0021(6) O2A 0.0336(9) 0.0411(8) 0.0346(11) 0.0052(8) 0.0045(8) 0.0021(6) Br1A 0.0336(9) 0.0411(8) 0.0346(11) 0.0052(8) 0.0045(8) 0.0021(6) C2B 0.0336(9) 0.0411(8) 0.0346(11) 0.0052(8) 0.0045(8) 0.0021(6) O2B 0.0336(9) 0.0411(8) 0.0346(11) 0.0052(8) 0.0045(8) 0.0021(6) Br1B 0.0336(9) 0.0411(8) 0.0346(11) 0.0052(8) 0.0045(8) 0.0021(6) Re1 0.02834(16) 0.02678(15) 0.02879(17) -0.0014(2) 0.00988(12) -0.0025(2) C14 0.058(7) 0.061(6) 0.046(6) 0.006(5) 0.011(5) -0.001(5) Cl1 0.0614(17) 0.0856(17) 0.0512(17) -0.0052(13) 0.0010(13) 0.0018(14) Cl2 0.105(2) 0.0596(14) 0.0718(18) -0.0031(16) 0.0082(15) -0.0084(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 C1 O1 1.153(7) . ? C1 Re1 1.894(8) . ? C2 N2 1.357(8) . ? C2 C3 1.371(9) . ? C2 H2 0.9300 . ? C3 C4 1.358(9) . ? C3 H3 0.9300 . ? C4 C5 1.404(9) . ? C4 H4 0.9300 . ? C5 N1 1.311(8) . ? C5 H5 0.9300 . ? C6 N4 1.323(8) . ? C6 C7 1.353(9) . ? C6 H6 0.9300 . ? C7 C8 1.348(9) . ? C7 H7 0.9300 . ? C8 C9 1.388(8) . ? C8 H8 0.9300 . ? C9 N3 1.350(8) . ? C9 H9 0.9300 . ? C10 N6 1.347(8) . ? C10 C11 1.379(8) . ? C10 H10 0.9300 . ? C11 C12 1.352(9) . ? C11 H11 0.9300 . ? C12 C13 1.384(8) . ? C12 H12 0.9300 . ? C13 N5 1.335(6) . ? C13 H13 0.9300 . ? N1 N2 1.328(6) . ? N1 Re1 2.129(5) . ? N3 N4 1.353(6) . ? N3 Re1 2.208(5) . ? N5 N6 1.325(7) . ? N5 Re1 2.126(5) . ? C2A O2A 1.276(13) . ? C2A Re1 1.825(10) . ? Br1A Re1 2.5822(13) . ? C2B O2B 1.280(14) . ? C2B Re1 1.827(11) . ? Br1B Re1 2.499(2) . ? C14 Cl2 1.747(6) . ? C14 Cl1 1.751(7) . ? C14 H14A 0.9700 . ? C14 H14B 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 O1 C1 Re1 174.9(7) . . ? N2 C2 C3 124.1(7) . . ? N2 C2 H2 117.9 . . ? C3 C2 H2 117.9 . . ? C4 C3 C2 116.3(7) . . ? C4 C3 H3 121.9 . . ? C2 C3 H3 121.9 . . ? C3 C4 C5 117.8(8) . . ? C3 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? N1 C5 C4 123.7(7) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? N4 C6 C7 125.8(8) . . ? N4 C6 H6 117.1 . . ? C7 C6 H6 117.1 . . ? C8 C7 C6 117.9(8) . . ? C8 C7 H7 121.1 . . ? C6 C7 H7 121.1 . . ? C7 C8 C9 117.6(7) . . ? C7 C8 H8 121.2 . . ? C9 C8 H8 121.2 . . ? N3 C9 C8 122.1(7) . . ? N3 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? N6 C10 C11 122.9(7) . . ? N6 C10 H10 118.6 . . ? C11 C10 H10 118.6 . . ? C12 C11 C10 117.0(7) . . ? C12 C11 H11 121.5 . . ? C10 C11 H11 121.5 . . ? C11 C12 C13 118.8(7) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? N5 C13 C12 122.5(7) . . ? N5 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C5 N1 N2 119.1(6) . . ? C5 N1 Re1 122.5(5) . . ? N2 N1 Re1 118.4(5) . . ? N1 N2 C2 118.9(6) . . ? C9 N3 N4 119.8(6) . . ? C9 N3 Re1 125.7(5) . . ? N4 N3 Re1 114.3(4) . . ? C6 N4 N3 116.8(6) . . ? N6 N5 C13 119.2(6) . . ? N6 N5 Re1 118.1(4) . . ? C13 N5 Re1 122.6(5) . . ? N5 N6 C10 119.7(6) . . ? O2A C2A Re1 175.9(10) . . ? O2B C2B Re1 173(3) . . ? C2A Re1 C2B 174.4(9) . . ? C2A Re1 C1 87.4(4) . . ? C2B Re1 C1 87.4(9) . . ? C2A Re1 N5 90.7(4) . . ? C2B Re1 N5 91.4(9) . . ? C1 Re1 N5 90.3(3) . . ? C2A Re1 N1 89.1(4) . . ? C2B Re1 N1 89.1(9) . . ? C1 Re1 N1 93.5(3) . . ? N5 Re1 N1 176.1(2) . . ? C2A Re1 N3 92.2(4) . . ? C2B Re1 N3 93.1(8) . . ? C1 Re1 N3 175.2(3) . . ? N5 Re1 N3 85.0(2) . . ? N1 Re1 N3 91.19(19) . . ? C2A Re1 Br1B 3.4(4) . . ? C2B Re1 Br1B 177.5(9) . . ? C1 Re1 Br1B 90.8(3) . . ? N5 Re1 Br1B 90.47(16) . . ? N1 Re1 Br1B 89.14(17) . . ? N3 Re1 Br1B 88.77(17) . . ? C2A Re1 Br1A 177.8(4) . . ? C2B Re1 Br1A 5.4(8) . . ? C1 Re1 Br1A 92.9(2) . . ? N5 Re1 Br1A 91.41(15) . . ? N1 Re1 Br1A 88.73(16) . . ? N3 Re1 Br1A 87.70(16) . . ? Br1B Re1 Br1A 175.84(8) . . ? Cl2 C14 Cl1 113.8(4) . . ? Cl2 C14 H14A 108.8 . . ? Cl1 C14 H14A 108.8 . . ? Cl2 C14 H14B 108.8 . . ? Cl1 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? 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 N2 C2 C3 C4 4.1(13) . . . . ? C2 C3 C4 C5 -1.8(12) . . . . ? C3 C4 C5 N1 -0.9(12) . . . . ? N4 C6 C7 C8 -2.1(13) . . . . ? C6 C7 C8 C9 0.6(12) . . . . ? C7 C8 C9 N3 1.3(11) . . . . ? N6 C10 C11 C12 -1.1(13) . . . . ? C10 C11 C12 C13 0.4(12) . . . . ? C11 C12 C13 N5 1.2(11) . . . . ? C4 C5 N1 N2 1.5(11) . . . . ? C4 C5 N1 Re1 179.6(5) . . . . ? C5 N1 N2 C2 0.7(10) . . . . ? Re1 N1 N2 C2 -177.5(5) . . . . ? C3 C2 N2 N1 -3.6(11) . . . . ? C8 C9 N3 N4 -2.0(10) . . . . ? C8 C9 N3 Re1 -176.4(5) . . . . ? C7 C6 N4 N3 1.5(12) . . . . ? C9 N3 N4 C6 0.6(10) . . . . ? Re1 N3 N4 C6 175.6(5) . . . . ? C12 C13 N5 N6 -2.2(10) . . . . ? C12 C13 N5 Re1 -179.6(5) . . . . ? C13 N5 N6 C10 1.5(10) . . . . ? Re1 N5 N6 C10 179.0(5) . . . . ? C11 C10 N6 N5 0.2(12) . . . . ? N6 N5 Re1 C2A -131.8(6) . . . . ? C13 N5 Re1 C2A 45.7(6) . . . . ? N6 N5 Re1 C2B 53.4(10) . . . . ? C13 N5 Re1 C2B -129.2(10) . . . . ? N6 N5 Re1 C1 140.8(5) . . . . ? C13 N5 Re1 C1 -41.7(6) . . . . ? N6 N5 Re1 N3 -39.6(5) . . . . ? C13 N5 Re1 N3 137.8(6) . . . . ? N6 N5 Re1 Br1B -128.4(5) . . . . ? C13 N5 Re1 Br1B 49.1(5) . . . . ? N6 N5 Re1 Br1A 47.9(5) . . . . ? C13 N5 Re1 Br1A -134.6(5) . . . . ? C5 N1 Re1 C2A -50.1(7) . . . . ? N2 N1 Re1 C2A 128.0(6) . . . . ? C5 N1 Re1 C2B 124.6(10) . . . . ? N2 N1 Re1 C2B -57.3(9) . . . . ? C5 N1 Re1 C1 37.2(6) . . . . ? N2 N1 Re1 C1 -144.6(5) . . . . ? C5 N1 Re1 N3 -142.3(6) . . . . ? N2 N1 Re1 N3 35.8(5) . . . . ? C5 N1 Re1 Br1B -53.5(6) . . . . ? N2 N1 Re1 Br1B 124.6(5) . . . . ? C5 N1 Re1 Br1A 130.1(6) . . . . ? N2 N1 Re1 Br1A -51.8(5) . . . . ? C9 N3 Re1 C2A -146.3(6) . . . . ? N4 N3 Re1 C2A 39.0(6) . . . . ? C9 N3 Re1 C2B 32.0(10) . . . . ? N4 N3 Re1 C2B -142.7(10) . . . . ? C9 N3 Re1 N5 123.1(6) . . . . ? N4 N3 Re1 N5 -51.6(5) . . . . ? C9 N3 Re1 N1 -57.2(6) . . . . ? N4 N3 Re1 N1 128.1(5) . . . . ? C9 N3 Re1 Br1B -146.3(5) . . . . ? N4 N3 Re1 Br1B 39.0(4) . . . . ? C9 N3 Re1 Br1A 31.5(5) . . . . ? N4 N3 Re1 Br1A -143.2(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.156 _refine_diff_density_min -0.734 _refine_diff_density_rms 0.135 #==END===#