# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 Cl N2 O4 Re' _chemical_formula_weight 503.90 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' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.5722(15) _cell_length_b 7.9755(5) _cell_length_c 18.3057(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.441(2) _cell_angle_gamma 90.00 _cell_volume 3129.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9933 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 30.96 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 7.957 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2667 _exptl_absorpt_correction_T_max 0.7671 _exptl_absorpt_process_details 'SADABS; Sheldrick, 2008 [Sheldrick, G. M. (2008)]' _exptl_special_details ; SADABS-2008 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1054 before and 0.0513 after correction. The estimated minimum and maximum transmission: 0.2667 0.7671. The l/2 correction factor is 0.0015. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 39281 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_unetI/netI 0.0444 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 31.09 _reflns_number_total 10044 _reflns_number_gt 8013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms were assigned ideal positions and refined isotropically as riding atoms. ; _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^)+(0.0285P)^2^+8.3853P] 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 10044 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0653 _refine_ls_wR_factor_gt 0.0581 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _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 0.14808(17) 0.4577(5) 0.3939(2) 0.0168(7) Uani 1 1 d . . . C2 C 0.20068(17) 0.4506(5) 0.2654(2) 0.0156(7) Uani 1 1 d . . . C3 C 0.23133(17) 0.6983(5) 0.3641(2) 0.0166(7) Uani 1 1 d . . . C4 C 0.17221(17) 0.7958(5) 0.1649(2) 0.0172(7) Uani 1 1 d . . . H4 H 0.1945 0.6978 0.1542 0.021 Uiso 1 1 calc R . . C5 C 0.16478(19) 0.9218(5) 0.1127(2) 0.0202(8) Uani 1 1 d . . . H5 H 0.1808 0.9089 0.0667 0.024 Uiso 1 1 calc R . . C6 C 0.1338(2) 1.0668(5) 0.1284(2) 0.0214(8) Uani 1 1 d . . . H6 H 0.1288 1.1560 0.0938 0.026 Uiso 1 1 calc R . . C7 C 0.11008(18) 1.0797(5) 0.1951(2) 0.0174(7) Uani 1 1 d . . . H7 H 0.0885 1.1779 0.2071 0.021 Uiso 1 1 calc R . . C8 C 0.11822(17) 0.9475(5) 0.24421(19) 0.0146(7) Uani 1 1 d . . . C9 C 0.09482(17) 0.9505(5) 0.3151(2) 0.0150(7) Uani 1 1 d . . . H9 H 0.0744 1.0470 0.3311 0.018 Uiso 1 1 calc R . . C10 C 0.07906(16) 0.8206(4) 0.42647(19) 0.0130(6) Uani 1 1 d . . . C11 C 0.03143(18) 0.7103(5) 0.4380(2) 0.0176(7) Uani 1 1 d . . . H11 H 0.0152 0.6343 0.4006 0.021 Uiso 1 1 calc R . . C12 C 0.00819(18) 0.7140(5) 0.5055(2) 0.0203(8) Uani 1 1 d . . . H12 H -0.0253 0.6418 0.5141 0.024 Uiso 1 1 calc R . . C13 C 0.03299(18) 0.8215(5) 0.5607(2) 0.0170(7) Uani 1 1 d . . . H13 H 0.0173 0.8208 0.6071 0.020 Uiso 1 1 calc R . . C14 C 0.08066(18) 0.9298(5) 0.54802(19) 0.0155(7) Uani 1 1 d . . . C15 C 0.10388(17) 0.9313(4) 0.4803(2) 0.0153(7) Uani 1 1 d . . . H15 H 0.1362 1.0068 0.4711 0.018 Uiso 1 1 calc R . . C16 C 0.35114(17) 0.3888(5) 0.3623(2) 0.0151(7) Uani 1 1 d . . . C17 C 0.30075(17) 0.3892(5) 0.4887(2) 0.0151(7) Uani 1 1 d . . . C18 C 0.26612(18) 0.1483(5) 0.3892(2) 0.0169(7) Uani 1 1 d . . . C19 C 0.31992(17) 0.0370(5) 0.5837(2) 0.0166(7) Uani 1 1 d . . . H19 H 0.2958 0.1328 0.5928 0.020 Uiso 1 1 calc R . . C20 C 0.32639(19) -0.0896(5) 0.6357(2) 0.0193(8) Uani 1 1 d . . . H20 H 0.3073 -0.0801 0.6798 0.023 Uiso 1 1 calc R . . C21 C 0.3609(2) -0.2299(5) 0.6226(2) 0.0232(8) Uani 1 1 d . . . H21 H 0.3653 -0.3188 0.6574 0.028 Uiso 1 1 calc R . . C22 C 0.3891(2) -0.2398(5) 0.5582(2) 0.0199(8) Uani 1 1 d . . . H22 H 0.4134 -0.3345 0.5480 0.024 Uiso 1 1 calc R . . C23 C 0.38071(17) -0.1080(5) 0.5094(2) 0.0146(7) Uani 1 1 d . . . C24 C 0.40772(18) -0.1073(5) 0.4396(2) 0.0161(7) Uani 1 1 d . . . H24 H 0.4321 -0.1990 0.4261 0.019 Uiso 1 1 calc R . . C25 C 0.42798(17) 0.0239(5) 0.33095(19) 0.0149(7) Uani 1 1 d . . . C26 C 0.48991(18) -0.0243(5) 0.3322(2) 0.0171(7) Uani 1 1 d . . . H26 H 0.5130 -0.0613 0.3765 0.021 Uiso 1 1 calc R . . C27 C 0.51723(18) -0.0172(5) 0.2675(2) 0.0205(8) Uani 1 1 d . . . H27 H 0.5594 -0.0519 0.2675 0.025 Uiso 1 1 calc R . . C28 C 0.48470(19) 0.0390(5) 0.2032(2) 0.0188(7) Uani 1 1 d . . . H28 H 0.5040 0.0427 0.1591 0.023 Uiso 1 1 calc R . . C29 C 0.42318(19) 0.0901(5) 0.2037(2) 0.0168(7) Uani 1 1 d . . . C30 C 0.39422(18) 0.0835(5) 0.2673(2) 0.0161(7) Uani 1 1 d . . . H30 H 0.3522 0.1189 0.2673 0.019 Uiso 1 1 calc R . . Cl1 Cl 0.05261(4) 0.51377(11) 0.25146(5) 0.01527(16) Uani 1 1 d . . . Cl2 Cl 0.44854(4) 0.30839(11) 0.49972(5) 0.01561(16) Uani 1 1 d . . . N1 N 0.14953(14) 0.8056(4) 0.22959(16) 0.0128(6) Uani 1 1 d . . . N2 N 0.10227(14) 0.8193(4) 0.35588(16) 0.0135(6) Uani 1 1 d . . . N3 N 0.34658(14) 0.0293(4) 0.52101(16) 0.0134(6) Uani 1 1 d . . . N4 N 0.39774(14) 0.0196(4) 0.39705(16) 0.0147(6) Uani 1 1 d . . . O1 O 0.14286(14) 0.3661(4) 0.44104(16) 0.0229(6) Uani 1 1 d . . . O2 O 0.22897(13) 0.3585(3) 0.23374(16) 0.0211(6) Uani 1 1 d . . . O3 O 0.27681(15) 0.7463(4) 0.39369(18) 0.0273(7) Uani 1 1 d . . . O4 O 0.10698(14) 1.0376(4) 0.60040(14) 0.0217(6) Uani 1 1 d . . . H4O H 0.0897 1.0260 0.6390 0.032 Uiso 1 1 calc R . . O5 O 0.35654(14) 0.4893(4) 0.31882(16) 0.0231(6) Uani 1 1 d . . . O6 O 0.27439(14) 0.4865(4) 0.51952(16) 0.0247(6) Uani 1 1 d . . . O7 O 0.21940(14) 0.1049(4) 0.36062(17) 0.0240(6) Uani 1 1 d . . . O8 O 0.38757(14) 0.1486(4) 0.14226(15) 0.0244(6) Uani 1 1 d . . . H8 H 0.4088 0.1482 0.1065 0.037 Uiso 1 1 calc R . . Re1 Re 0.154640(6) 0.613124(17) 0.314759(7) 0.01123(4) Uani 1 1 d . . . Re2 Re 0.344293(6) 0.224194(17) 0.437761(7) 0.01139(4) 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 0.0159(17) 0.0185(17) 0.0162(16) 0.0013(14) 0.0024(13) 0.0019(14) C2 0.0164(17) 0.0158(16) 0.0147(16) 0.0040(13) 0.0021(13) -0.0014(14) C3 0.0158(17) 0.0163(18) 0.0180(17) 0.0006(14) 0.0033(14) 0.0040(14) C4 0.0159(17) 0.0197(18) 0.0172(17) 0.0001(14) 0.0064(14) 0.0005(14) C5 0.0194(18) 0.025(2) 0.0173(17) 0.0036(15) 0.0057(15) -0.0036(15) C6 0.025(2) 0.0199(19) 0.0198(18) 0.0077(15) 0.0040(16) 0.0008(16) C7 0.0190(18) 0.0148(17) 0.0178(17) 0.0027(13) -0.0011(14) 0.0008(13) C8 0.0132(16) 0.0175(17) 0.0130(15) -0.0002(13) 0.0015(13) -0.0009(13) C9 0.0131(15) 0.0142(16) 0.0176(17) 0.0000(14) 0.0011(13) 0.0028(13) C10 0.0136(15) 0.0138(16) 0.0123(15) -0.0009(12) 0.0052(13) 0.0023(13) C11 0.0176(17) 0.0206(18) 0.0148(16) -0.0029(14) 0.0026(14) -0.0020(15) C12 0.0149(17) 0.0245(19) 0.0224(19) -0.0010(16) 0.0055(15) -0.0042(15) C13 0.0196(17) 0.0180(17) 0.0145(16) -0.0003(14) 0.0064(14) 0.0023(14) C14 0.0184(17) 0.0150(17) 0.0130(16) 0.0000(13) 0.0014(13) 0.0036(13) C15 0.0147(16) 0.0125(16) 0.0188(17) 0.0004(13) 0.0018(14) -0.0030(13) C16 0.0114(15) 0.0177(17) 0.0163(16) 0.0002(13) 0.0018(13) 0.0009(13) C17 0.0118(16) 0.0179(17) 0.0159(16) 0.0020(13) 0.0026(13) -0.0001(13) C18 0.0203(18) 0.0131(17) 0.0182(17) 0.0043(13) 0.0055(14) 0.0056(14) C19 0.0161(16) 0.0168(17) 0.0172(17) -0.0024(14) 0.0035(14) -0.0025(14) C20 0.0194(18) 0.0213(19) 0.0177(18) 0.0007(14) 0.0048(15) -0.0029(14) C21 0.028(2) 0.023(2) 0.0185(19) 0.0072(15) 0.0042(17) -0.0002(16) C22 0.0206(19) 0.0192(19) 0.0200(19) 0.0044(14) 0.0028(16) 0.0030(14) C23 0.0118(15) 0.0173(17) 0.0141(16) 0.0003(13) -0.0015(13) 0.0007(13) C24 0.0164(17) 0.0168(17) 0.0153(17) -0.0012(13) 0.0019(14) 0.0010(14) C25 0.0164(16) 0.0148(17) 0.0139(16) -0.0049(13) 0.0036(13) -0.0022(13) C26 0.0166(17) 0.0182(18) 0.0162(16) 0.0021(14) 0.0004(14) 0.0048(14) C27 0.0155(17) 0.025(2) 0.0222(18) 0.0010(15) 0.0056(15) 0.0040(15) C28 0.0218(18) 0.0183(18) 0.0175(17) -0.0010(14) 0.0082(14) 0.0000(15) C29 0.0200(18) 0.0150(17) 0.0153(17) 0.0003(13) 0.0015(14) -0.0030(13) C30 0.0165(17) 0.0166(18) 0.0153(16) -0.0022(13) 0.0019(14) 0.0011(13) Cl1 0.0130(4) 0.0195(4) 0.0130(4) -0.0017(3) 0.0001(3) -0.0013(3) Cl2 0.0121(4) 0.0201(4) 0.0144(4) -0.0027(3) 0.0002(3) -0.0008(3) N1 0.0127(13) 0.0141(14) 0.0117(13) 0.0023(11) 0.0010(11) -0.0017(11) N2 0.0110(13) 0.0163(14) 0.0132(13) -0.0006(11) 0.0010(11) -0.0010(11) N3 0.0136(14) 0.0142(14) 0.0125(13) -0.0013(11) 0.0013(11) 0.0000(11) N4 0.0122(13) 0.0181(15) 0.0140(14) -0.0013(11) 0.0029(11) 0.0022(11) O1 0.0248(15) 0.0235(15) 0.0212(14) 0.0075(11) 0.0056(12) 0.0040(12) O2 0.0222(14) 0.0178(14) 0.0245(14) -0.0022(11) 0.0077(12) 0.0042(11) O3 0.0220(16) 0.0253(16) 0.0325(17) 0.0010(12) -0.0054(14) -0.0012(12) O4 0.0296(15) 0.0225(14) 0.0134(12) -0.0055(11) 0.0047(11) -0.0065(12) O5 0.0223(14) 0.0242(15) 0.0243(14) 0.0073(12) 0.0087(12) 0.0034(12) O6 0.0245(15) 0.0261(15) 0.0241(14) -0.0052(12) 0.0054(12) 0.0085(12) O7 0.0187(14) 0.0220(14) 0.0302(16) 0.0009(12) -0.0011(12) -0.0032(11) O8 0.0251(15) 0.0333(17) 0.0152(13) 0.0022(12) 0.0033(11) 0.0034(13) Re1 0.01011(6) 0.01229(6) 0.01140(6) 0.00107(5) 0.00165(5) 0.00063(5) Re2 0.00978(6) 0.01306(6) 0.01148(6) 0.00006(5) 0.00189(5) 0.00103(5) _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 1.145(4) . ? C1 Re1 1.924(4) . ? C2 O2 1.152(4) . ? C2 Re1 1.920(4) . ? C3 O3 1.133(5) . ? C3 Re1 1.918(4) . ? C4 N1 1.334(4) . ? C4 C5 1.384(5) . ? C4 H4 0.9500 . ? C5 C6 1.382(6) . ? C5 H5 0.9500 . ? C6 C7 1.379(5) . ? C6 H6 0.9500 . ? C7 C8 1.385(5) . ? C7 H7 0.9500 . ? C8 N1 1.360(5) . ? C8 C9 1.444(5) . ? C9 N2 1.285(5) . ? C9 H9 0.9500 . ? C10 C15 1.385(5) . ? C10 C11 1.387(5) . ? C10 N2 1.437(4) . ? C11 C12 1.385(5) . ? C11 H11 0.9500 . ? C12 C13 1.386(5) . ? C12 H12 0.9500 . ? C13 C14 1.382(5) . ? C13 H13 0.9500 . ? C14 O4 1.363(4) . ? C14 C15 1.388(5) . ? C15 H15 0.9500 . ? C16 O5 1.144(4) . ? C16 Re2 1.924(4) . ? C17 O6 1.147(4) . ? C17 Re2 1.918(4) . ? C18 O7 1.136(5) . ? C18 Re2 1.914(4) . ? C19 N3 1.342(4) . ? C19 C20 1.383(5) . ? C19 H19 0.9500 . ? C20 C21 1.379(6) . ? C20 H20 0.9500 . ? C21 C22 1.389(6) . ? C21 H21 0.9500 . ? C22 C23 1.378(5) . ? C22 H22 0.9500 . ? C23 N3 1.350(5) . ? C23 C24 1.462(5) . ? C24 N4 1.280(5) . ? C24 H24 0.9500 . ? C25 C30 1.388(5) . ? C25 C26 1.388(5) . ? C25 N4 1.438(4) . ? C26 C27 1.381(5) . ? C26 H26 0.9500 . ? C27 C28 1.377(5) . ? C27 H27 0.9500 . ? C28 C29 1.389(5) . ? C28 H28 0.9500 . ? C29 O8 1.371(5) . ? C29 C30 1.382(5) . ? C30 H30 0.9500 . ? Cl1 Re1 2.4986(9) . ? Cl2 Re2 2.4945(9) . ? N1 Re1 2.182(3) . ? N2 Re1 2.177(3) . ? N3 Re2 2.173(3) . ? N4 Re2 2.177(3) . ? O4 H4O 0.8400 . ? O8 H8 0.8400 . ? 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 178.5(3) . . ? O2 C2 Re1 177.1(3) . . ? O3 C3 Re1 179.0(4) . . ? N1 C4 C5 123.1(4) . . ? N1 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? C6 C5 C4 119.0(4) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C7 C6 C5 118.9(4) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C8 119.1(4) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? N1 C8 C7 122.4(3) . . ? N1 C8 C9 115.0(3) . . ? C7 C8 C9 122.7(3) . . ? N2 C9 C8 118.4(3) . . ? N2 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C15 C10 C11 122.0(3) . . ? C15 C10 N2 119.9(3) . . ? C11 C10 N2 118.1(3) . . ? C12 C11 C10 118.0(4) . . ? C12 C11 H11 121.0 . . ? C10 C11 H11 121.0 . . ? C11 C12 C13 121.0(4) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 119.8(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? O4 C14 C13 122.3(3) . . ? O4 C14 C15 117.3(3) . . ? C13 C14 C15 120.4(3) . . ? C10 C15 C14 118.7(3) . . ? C10 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? O5 C16 Re2 177.9(4) . . ? O6 C17 Re2 179.2(4) . . ? O7 C18 Re2 179.2(4) . . ? N3 C19 C20 122.3(4) . . ? N3 C19 H19 118.8 . . ? C20 C19 H19 118.8 . . ? C21 C20 C19 119.2(4) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C20 C21 C22 119.3(4) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C23 C22 C21 118.0(4) . . ? C23 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? N3 C23 C22 123.4(3) . . ? N3 C23 C24 114.4(3) . . ? C22 C23 C24 122.2(3) . . ? N4 C24 C23 118.5(3) . . ? N4 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C30 C25 C26 121.5(3) . . ? C30 C25 N4 118.1(3) . . ? C26 C25 N4 120.4(3) . . ? C27 C26 C25 118.5(4) . . ? C27 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? C28 C27 C26 121.4(4) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? C27 C28 C29 119.0(3) . . ? C27 C28 H28 120.5 . . ? C29 C28 H28 120.5 . . ? O8 C29 C30 116.0(3) . . ? O8 C29 C28 122.8(3) . . ? C30 C29 C28 121.1(4) . . ? C29 C30 C25 118.4(4) . . ? C29 C30 H30 120.8 . . ? C25 C30 H30 120.8 . . ? C4 N1 C8 117.6(3) . . ? C4 N1 Re1 126.8(3) . . ? C8 N1 Re1 115.6(2) . . ? C9 N2 C10 118.9(3) . . ? C9 N2 Re1 116.7(2) . . ? C10 N2 Re1 124.3(2) . . ? C19 N3 C23 117.8(3) . . ? C19 N3 Re2 126.1(3) . . ? C23 N3 Re2 116.1(2) . . ? C24 N4 C25 118.0(3) . . ? C24 N4 Re2 116.3(2) . . ? C25 N4 Re2 125.3(2) . . ? C14 O4 H4O 109.5 . . ? C29 O8 H8 109.5 . . ? C3 Re1 C2 89.81(16) . . ? C3 Re1 C1 90.33(16) . . ? C2 Re1 C1 90.31(15) . . ? C3 Re1 N2 91.32(13) . . ? C2 Re1 N2 171.48(13) . . ? C1 Re1 N2 98.13(14) . . ? C3 Re1 N1 93.40(14) . . ? C2 Re1 N1 97.23(13) . . ? C1 Re1 N1 171.59(13) . . ? N2 Re1 N1 74.28(11) . . ? C3 Re1 Cl1 177.57(11) . . ? C2 Re1 Cl1 92.45(11) . . ? C1 Re1 Cl1 90.54(12) . . ? N2 Re1 Cl1 86.31(8) . . ? N1 Re1 Cl1 85.44(8) . . ? C18 Re2 C17 89.35(16) . . ? C18 Re2 C16 90.97(15) . . ? C17 Re2 C16 87.83(15) . . ? C18 Re2 N3 92.80(13) . . ? C17 Re2 N3 97.10(13) . . ? C16 Re2 N3 173.82(13) . . ? C18 Re2 N4 94.40(14) . . ? C17 Re2 N4 170.94(14) . . ? C16 Re2 N4 100.33(13) . . ? N3 Re2 N4 74.50(11) . . ? C18 Re2 Cl2 176.97(11) . . ? C17 Re2 Cl2 93.45(11) . . ? C16 Re2 Cl2 90.29(11) . . ? N3 Re2 Cl2 85.72(8) . . ? N4 Re2 Cl2 82.67(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.09 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.348 _refine_diff_density_min -1.467 _refine_diff_density_rms 0.175 _database_code_depnum_ccdc_archive 'CCDC 929875' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H9 Cl N2 O4 Re' _chemical_formula_weight 502.89 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' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 13.005(3) _cell_length_b 8.8892(18) _cell_length_c 13.661(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.583(2) _cell_angle_gamma 90.00 _cell_volume 1552.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2671 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 23.20 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 8.020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4352 _exptl_absorpt_correction_T_max 0.7450 _exptl_absorpt_process_details 'SADABS; Sheldrick, 2008 [Sheldrick, G. M. (2008)]' _exptl_special_details ; SADABS-2008 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1408 before and 0.0570 after correction. The estimated minimum and maximum transmission: 0.4352 0.7450. The l/2 correction factor is 0.0015. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9681 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_unetI/netI 0.0453 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 23.85 _reflns_number_total 2393 _reflns_number_gt 2044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms were assigned ideal positions and refined isotropically as riding atoms. ; _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^)+(0.0000P)^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 2393 _refine_ls_number_parameters 246 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0548 _refine_ls_wR_factor_gt 0.0524 _refine_ls_goodness_of_fit_ref 1.277 _refine_ls_restrained_S_all 1.291 _refine_ls_shift/su_max 0.009 _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 1.0022(6) 0.8703(7) 0.3448(5) 0.0270(17) Uani 1 1 d . . . C2 C 1.2046(6) 0.8683(7) 0.3293(5) 0.0271(17) Uani 1 1 d . . . C3 C 1.0664(14) 1.028(2) 0.2041(11) 0.022(4) Uani 0.70 1 d P A 2 C4 C 1.2540(5) 0.7509(8) 0.1154(5) 0.0288(18) Uani 1 1 d . . . H4 H 1.3000 0.7812 0.1724 0.035 Uiso 1 1 calc R . . C5 C 1.2944(5) 0.7050(7) 0.0338(5) 0.0317(18) Uani 1 1 d . . . H5 H 1.3662 0.7049 0.0356 0.038 Uiso 1 1 calc R . . C6 C 1.2262(5) 0.6592(7) -0.0507(5) 0.0285(17) Uani 1 1 d . . . H6 H 1.2516 0.6257 -0.1062 0.034 Uiso 1 1 calc R . . C7 C 1.1205(6) 0.6639(7) -0.0518(5) 0.0300(18) Uani 1 1 d . . . H7 H 1.0734 0.6353 -0.1085 0.036 Uiso 1 1 calc R . . C8 C 1.0849(5) 0.7115(6) 0.0326(5) 0.0204(16) Uani 1 1 d . . . C9 C 0.9750(5) 0.7192(7) 0.0391(5) 0.0262(17) Uani 1 1 d . B . H9 H 0.9238 0.6970 -0.0161 0.031 Uiso 1 1 calc R . . C10 C 0.8397(5) 0.7669(8) 0.1264(5) 0.0304(18) Uani 1 1 d . B . C11 C 0.7712(6) 0.8517(10) 0.0611(6) 0.052(2) Uani 1 1 d D . . C12 C 0.6660(8) 0.8556(12) 0.0663(7) 0.081(4) Uani 1 1 d . B . H12 H 0.6193 0.9104 0.0200 0.098 Uiso 1 1 calc R . . C13 C 0.6312(8) 0.7771(14) 0.1409(9) 0.086(4) Uani 1 1 d . . . H13 H 0.5610 0.7822 0.1464 0.104 Uiso 1 1 calc R B . C14 C 0.6981(8) 0.6929(11) 0.2062(7) 0.065(3) Uani 1 1 d . B . H14 H 0.6743 0.6368 0.2550 0.078 Uiso 1 1 calc R . . C15 C 0.8019(6) 0.6918(9) 0.1990(6) 0.043(2) Uani 1 1 d D . . C16 C 1.087(2) 0.617(3) 0.289(2) 0.012(8) Uani 0.30 1 d PU A 1 Cl1 Cl 1.0613(10) 1.0622(15) 0.1620(8) 0.036(3) Uani 0.30 1 d P A 1 Cl2 Cl 1.0874(3) 0.5518(5) 0.2848(3) 0.0389(10) Uani 0.70 1 d P A 2 N1 N 1.1515(4) 0.7538(6) 0.1160(4) 0.0207(13) Uani 1 1 d . . . N2 N 0.9495(4) 0.7570(6) 0.1218(4) 0.0235(13) Uani 1 1 d . . . O1 O 0.9579(4) 0.9002(6) 0.4060(4) 0.0398(14) Uani 1 1 d . . . O2 O 1.2823(4) 0.9000(5) 0.3815(4) 0.0410(14) Uani 1 1 d . . . O3 O 1.0612(6) 1.1544(9) 0.1855(6) 0.033(2) Uani 0.70 1 d P A 2 O4 O 0.7954(7) 0.9115(9) -0.0214(7) 0.043(3) Uani 0.55 1 d PD B 1 H4O H 0.8321 0.9861 -0.0068 0.064 Uiso 0.55 1 calc PR B 1 O5 O 0.8523(9) 0.5979(13) 0.2672(9) 0.054(3) Uani 0.45 1 d PD B 2 H5O H 0.9153 0.6023 0.2671 0.082 Uiso 0.45 1 calc PR B 2 O6 O 1.0862(18) 0.492(2) 0.3258(19) 0.052(7) Uani 0.30 1 d P A 1 Re1 Re 1.07814(2) 0.81948(3) 0.240235(19) 0.02134(11) Uani 1 1 d . A . 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 0.026(4) 0.032(4) 0.023(4) 0.003(3) 0.003(4) 0.002(3) C2 0.027(5) 0.032(4) 0.025(4) 0.001(3) 0.011(4) 0.008(3) C3 0.009(6) 0.038(12) 0.020(9) -0.002(7) 0.008(7) -0.002(7) C4 0.016(4) 0.040(4) 0.029(4) 0.001(4) 0.001(3) -0.004(3) C5 0.019(4) 0.045(5) 0.032(4) 0.003(4) 0.008(4) 0.000(4) C6 0.028(5) 0.034(4) 0.027(4) 0.004(3) 0.014(4) 0.004(4) C7 0.032(5) 0.035(4) 0.023(4) 0.002(3) 0.005(3) 0.001(4) C8 0.021(4) 0.017(4) 0.024(4) 0.001(3) 0.004(3) -0.003(3) C9 0.018(4) 0.030(4) 0.030(4) 0.004(3) 0.002(3) -0.003(3) C10 0.018(4) 0.048(5) 0.027(4) -0.020(4) 0.007(4) -0.003(4) C11 0.030(5) 0.075(7) 0.053(6) -0.013(5) 0.012(5) 0.027(5) C12 0.045(7) 0.140(11) 0.053(7) -0.031(7) -0.007(5) 0.053(7) C13 0.028(6) 0.157(12) 0.076(9) -0.085(8) 0.017(6) -0.012(7) C14 0.052(7) 0.099(8) 0.053(6) -0.045(6) 0.033(5) -0.053(6) C15 0.030(5) 0.062(6) 0.042(5) -0.038(5) 0.019(4) -0.028(5) C16 0.013(8) 0.012(8) 0.012(8) -0.001(2) 0.002(2) 0.000(2) Cl1 0.031(5) 0.028(6) 0.046(7) 0.010(6) 0.000(6) -0.011(4) Cl2 0.045(2) 0.026(3) 0.053(3) 0.016(2) 0.0267(18) 0.010(2) N1 0.021(3) 0.022(3) 0.019(3) 0.001(2) 0.005(3) -0.004(3) N2 0.029(4) 0.021(3) 0.021(3) -0.001(3) 0.008(3) -0.004(3) O1 0.035(3) 0.057(4) 0.031(3) -0.009(3) 0.014(3) -0.002(3) O2 0.025(3) 0.049(3) 0.041(3) -0.006(3) -0.013(3) 0.007(3) O3 0.029(5) 0.026(5) 0.044(5) 0.005(5) 0.001(4) -0.001(4) O4 0.031(6) 0.032(6) 0.072(7) 0.022(5) 0.026(5) 0.011(4) O5 0.043(8) 0.061(9) 0.059(9) -0.002(7) 0.009(8) -0.006(7) O6 0.043(13) 0.033(16) 0.09(2) 0.018(12) 0.025(14) 0.002(11) Re1 0.01944(17) 0.02570(17) 0.01864(16) 0.00105(14) 0.00290(12) -0.00014(14) _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 1.130(8) . ? C1 Re1 1.934(8) . ? C2 O2 1.160(7) . ? C2 Re1 1.907(7) . ? C3 O3 1.149(19) . ? C3 Re1 1.919(17) . ? C4 N1 1.334(8) . ? C4 C5 1.379(9) . ? C5 C6 1.381(9) . ? C6 C7 1.373(9) . ? C7 C8 1.386(9) . ? C8 N1 1.352(7) . ? C8 C9 1.450(9) . ? C9 N2 1.280(8) . ? C10 C15 1.360(10) . ? C10 C11 1.366(10) . ? C10 N2 1.443(8) . ? C11 O4 1.335(5) . ? C11 C12 1.384(12) . ? C12 C13 1.378(14) . ? C13 C14 1.353(13) . ? C14 C15 1.371(11) . ? C15 O5 1.331(5) . ? C16 O6 1.22(3) . ? C16 Re1 1.92(3) . ? Cl1 Re1 2.399(12) . ? Cl2 Re1 2.454(4) . ? N1 Re1 2.174(5) . ? N2 Re1 2.175(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 Re1 179.9(7) . . ? O2 C2 Re1 178.2(6) . . ? O3 C3 Re1 177.7(15) . . ? N1 C4 C5 122.7(6) . . ? C4 C5 C6 118.8(7) . . ? C7 C6 C5 119.2(7) . . ? C6 C7 C8 119.2(7) . . ? N1 C8 C7 121.7(6) . . ? N1 C8 C9 115.0(6) . . ? C7 C8 C9 123.3(6) . . ? N2 C9 C8 118.9(6) . . ? C15 C10 C11 117.9(7) . . ? C15 C10 N2 119.7(7) . . ? C11 C10 N2 122.4(7) . . ? O4 C11 C10 123.0(8) . . ? O4 C11 C12 115.0(9) . . ? C10 C11 C12 120.8(8) . . ? C13 C12 C11 119.2(9) . . ? C14 C13 C12 120.6(9) . . ? C13 C14 C15 118.6(10) . . ? O5 C15 C10 128.4(9) . . ? O5 C15 C14 108.6(10) . . ? C10 C15 C14 122.8(9) . . ? O6 C16 Re1 174(3) . . ? C4 N1 C8 118.5(6) . . ? C4 N1 Re1 126.3(5) . . ? C8 N1 Re1 115.2(4) . . ? C9 N2 C10 118.2(6) . . ? C9 N2 Re1 115.8(5) . . ? C10 N2 Re1 125.7(4) . . ? C2 Re1 C16 90.2(9) . . ? C2 Re1 C3 87.9(6) . . ? C16 Re1 C3 174.3(10) . . ? C2 Re1 C1 88.4(3) . . ? C16 Re1 C1 88.2(9) . . ? C3 Re1 C1 86.4(5) . . ? C2 Re1 N1 96.2(2) . . ? C16 Re1 N1 90.7(9) . . ? C3 Re1 N1 94.8(5) . . ? C1 Re1 N1 175.2(2) . . ? C2 Re1 N2 171.1(2) . . ? C16 Re1 N2 90.4(9) . . ? C3 Re1 N2 92.3(5) . . ? C1 Re1 N2 100.5(2) . . ? N1 Re1 N2 74.9(2) . . ? C2 Re1 Cl1 94.4(4) . . ? C16 Re1 Cl1 174.0(9) . . ? C3 Re1 Cl1 11.3(7) . . ? C1 Re1 Cl1 95.8(4) . . ? N1 Re1 Cl1 84.9(4) . . ? N2 Re1 Cl1 84.5(3) . . ? C2 Re1 Cl2 93.7(2) . . ? C16 Re1 Cl2 5.9(9) . . ? C3 Re1 Cl2 178.3(5) . . ? C1 Re1 Cl2 92.9(2) . . ? N1 Re1 Cl2 85.67(16) . . ? N2 Re1 Cl2 86.18(17) . . ? Cl1 Re1 Cl2 168.2(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.85 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.883 _refine_diff_density_min -1.051 _refine_diff_density_rms 0.145 _database_code_depnum_ccdc_archive 'CCDC 929876' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 Br N2 O4 Re' _chemical_formula_weight 548.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 12.4869(15) _cell_length_b 9.2091(11) _cell_length_c 13.9549(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.1460(10) _cell_angle_gamma 90.00 _cell_volume 1579.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5375 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.15 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 10.242 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3989 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details 'SADABS; Sheldrick, 2008 [Sheldrick, G. M. (2008)]' _exptl_special_details ; SADABS-2008 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1510 before and 0.0633 after correction. The estimated minimum and maximum transmission: 0.3989 0.7455. The l/2 correction factor is 0.0015. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12874 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_unetI/netI 0.0490 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.17 _reflns_number_total 3492 _reflns_number_gt 2995 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms were assigned ideal positions and refined isotropically as riding atoms. The high residual peak is due to the minor disorder often seen along the axis shared by the halide and one of the carbonyls bound to the rhenium atom. This peak represents the bromide atom's position if the axial positions were swapped and we chose not to model this. ; _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^)+(0.0717P)^2^+23.7008P] 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 3492 _refine_ls_number_parameters 209 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 0.811 _refine_ls_restrained_S_all 0.821 _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 Br1 Br 1.06574(6) 1.05773(8) 0.14537(5) 0.02549(17) Uani 1 1 d . . . C1 C 1.0240(5) 0.8833(7) 0.3397(5) 0.0190(13) Uani 1 1 d . . . C2 C 1.2361(6) 0.8778(7) 0.3148(5) 0.0185(13) Uani 1 1 d . . . C3 C 1.1175(6) 0.6302(4) 0.3109(5) 0.0260(15) Uani 1 1 d DU . . C4 C 1.2726(6) 0.7274(7) 0.1118(5) 0.0201(14) Uani 1 1 d . . . H4 H 1.3240 0.7569 0.1648 0.024 Uiso 1 1 calc R . . C5 C 1.3077(6) 0.6743(7) 0.0294(5) 0.0218(14) Uani 1 1 d . . . H5 H 1.3817 0.6671 0.0279 0.026 Uiso 1 1 calc R . . C6 C 1.2329(6) 0.6329(8) -0.0492(5) 0.0233(14) Uani 1 1 d . . . H6 H 1.2556 0.5965 -0.1045 0.028 Uiso 1 1 calc R . . C7 C 1.1228(6) 0.6455(7) -0.0462(5) 0.0206(14) Uani 1 1 d . . . H7 H 1.0705 0.6188 -0.0992 0.025 Uiso 1 1 calc R . . C8 C 1.0932(5) 0.6984(7) 0.0376(5) 0.0164(13) Uani 1 1 d . . . C9 C 0.9802(6) 0.7045(7) 0.0519(5) 0.0182(13) Uani 1 1 d . . . H9 H 0.9236 0.6832 0.0011 0.022 Uiso 1 1 calc R . . C10 C 0.8492(6) 0.7425(8) 0.1502(5) 0.0211(14) Uani 1 1 d . . . C11 C 0.8221(6) 0.6690(7) 0.2283(5) 0.0205(14) Uani 1 1 d . . . H11 H 0.8755 0.6204 0.2713 0.025 Uiso 1 1 calc R . . C12 C 0.7139(6) 0.6673(8) 0.2429(5) 0.0216(14) Uani 1 1 d . . . H12 H 0.6950 0.6152 0.2945 0.026 Uiso 1 1 calc R . . C13 C 0.6355(6) 0.7431(8) 0.1804(6) 0.0260(15) Uani 1 1 d . . . C14 C 0.6625(6) 0.8175(8) 0.1010(6) 0.0289(17) Uani 1 1 d . . . H14 H 0.6092 0.8674 0.0586 0.035 Uiso 1 1 calc R . . C15 C 0.7705(6) 0.8168(8) 0.0853(6) 0.0231(15) Uani 1 1 d . . . H15 H 0.7893 0.8652 0.0322 0.028 Uiso 1 1 calc R . . N1 N 1.1668(4) 0.7371(6) 0.1168(4) 0.0160(11) Uani 1 1 d . . . N2 N 0.9607(5) 0.7396(6) 0.1353(4) 0.0193(11) Uani 1 1 d . . . O1 O 0.9768(4) 0.9249(6) 0.3988(4) 0.0302(12) Uani 1 1 d . . . O2 O 1.3196(4) 0.9141(5) 0.3562(4) 0.0256(11) Uani 1 1 d . . . O3 O 1.1283(5) 0.5296(4) 0.3594(4) 0.0367(13) Uani 1 1 d DU . . O4 O 0.5302(4) 0.7511(7) 0.1928(4) 0.0323(13) Uani 1 1 d . . . H4O H 0.5210 0.6972 0.2374 0.048 Uiso 1 1 calc R . . Re1 Re 1.099645(19) 0.81293(3) 0.241255(17) 0.01493(11) Uani 1 1 d 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 Br1 0.0298(4) 0.0213(3) 0.0253(4) 0.0025(3) 0.0046(3) 0.0023(3) C1 0.019(3) 0.021(3) 0.017(3) 0.005(3) 0.004(3) -0.001(3) C2 0.023(3) 0.014(3) 0.018(3) 0.001(3) 0.001(3) 0.006(3) C3 0.023(2) 0.034(2) 0.021(2) -0.0040(17) 0.0025(17) 0.0077(17) C4 0.022(3) 0.018(3) 0.019(3) -0.002(3) 0.000(3) 0.002(3) C5 0.023(3) 0.019(3) 0.025(4) 0.000(3) 0.009(3) 0.003(3) C6 0.028(4) 0.024(3) 0.020(3) -0.002(3) 0.007(3) 0.001(3) C7 0.023(3) 0.018(3) 0.021(3) 0.001(3) 0.003(3) -0.003(3) C8 0.018(3) 0.015(3) 0.016(3) 0.001(2) 0.004(3) 0.001(2) C9 0.018(3) 0.017(3) 0.019(3) -0.001(2) 0.001(3) 0.005(2) C10 0.020(3) 0.020(3) 0.024(3) -0.007(3) 0.006(3) -0.005(3) C11 0.021(3) 0.024(3) 0.016(3) -0.001(3) 0.002(3) -0.003(3) C12 0.024(3) 0.025(3) 0.017(3) 0.002(3) 0.006(3) -0.005(3) C13 0.018(3) 0.027(4) 0.034(4) -0.004(3) 0.006(3) -0.001(3) C14 0.023(4) 0.035(4) 0.028(4) 0.007(3) 0.001(3) 0.007(3) C15 0.020(3) 0.027(4) 0.022(4) 0.004(3) 0.002(3) -0.001(3) N1 0.017(3) 0.014(2) 0.018(3) 0.001(2) 0.004(2) 0.002(2) N2 0.019(3) 0.017(3) 0.021(3) 0.000(2) 0.003(2) -0.001(2) O1 0.031(3) 0.035(3) 0.027(3) -0.005(2) 0.012(2) -0.004(2) O2 0.023(3) 0.023(3) 0.028(3) -0.006(2) -0.005(2) 0.002(2) O3 0.037(2) 0.034(2) 0.041(2) -0.0074(16) 0.0115(16) -0.0043(16) O4 0.023(3) 0.042(3) 0.035(3) 0.006(3) 0.014(2) 0.005(2) Re1 0.01653(16) 0.01471(15) 0.01339(16) -0.00097(9) 0.00217(10) -0.00056(9) _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 Br1 Re1 2.6177(8) . ? C1 O1 1.159(9) . ? C1 Re1 1.913(7) . ? C2 O2 1.149(8) . ? C2 Re1 1.923(7) . ? C3 O3 1.141(2) . ? C3 Re1 1.937(2) . ? C4 N1 1.339(9) . ? C4 C5 1.390(10) . ? C4 H4 0.9300 . ? C5 C6 1.364(10) . ? C5 H5 0.9300 . ? C6 C7 1.389(10) . ? C6 H6 0.9300 . ? C7 C8 1.376(10) . ? C7 H7 0.9300 . ? C8 N1 1.355(8) . ? C8 C9 1.461(9) . ? C9 N2 1.272(9) . ? C9 H9 0.9300 . ? C10 C11 1.375(10) . ? C10 C15 1.393(10) . ? C10 N2 1.444(9) . ? C11 C12 1.402(10) . ? C11 H11 0.9300 . ? C12 C13 1.381(10) . ? C12 H12 0.9300 . ? C13 O4 1.357(9) . ? C13 C14 1.394(11) . ? C14 C15 1.405(11) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N1 Re1 2.173(6) . ? N2 Re1 2.179(6) . ? O4 H4O 0.8200 . ? 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 179.1(6) . . ? O2 C2 Re1 177.5(6) . . ? O3 C3 Re1 173.9(7) . . ? N1 C4 C5 121.6(6) . . ? N1 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C6 C5 C4 119.6(7) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 119.6(7) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 118.1(6) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? N1 C8 C7 122.8(6) . . ? N1 C8 C9 114.3(6) . . ? C7 C8 C9 122.7(6) . . ? N2 C9 C8 118.7(6) . . ? N2 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C11 C10 C15 120.9(7) . . ? C11 C10 N2 118.9(6) . . ? C15 C10 N2 120.2(6) . . ? C10 C11 C12 119.9(7) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 119.8(7) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? O4 C13 C12 122.8(7) . . ? O4 C13 C14 116.8(7) . . ? C12 C13 C14 120.4(7) . . ? C13 C14 C15 119.7(7) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C10 C15 C14 119.2(7) . . ? C10 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C4 N1 C8 118.3(6) . . ? C4 N1 Re1 125.9(5) . . ? C8 N1 Re1 115.8(4) . . ? C9 N2 C10 118.8(6) . . ? C9 N2 Re1 116.2(5) . . ? C10 N2 Re1 124.7(4) . . ? C13 O4 H4O 109.5 . . ? C1 Re1 C2 90.9(3) . . ? C1 Re1 C3 87.8(3) . . ? C2 Re1 C3 89.4(3) . . ? C1 Re1 N1 172.9(2) . . ? C2 Re1 N1 95.5(2) . . ? C3 Re1 N1 95.5(3) . . ? C1 Re1 N2 99.1(3) . . ? C2 Re1 N2 169.5(3) . . ? C3 Re1 N2 94.5(3) . . ? N1 Re1 N2 74.4(2) . . ? C1 Re1 Br1 91.1(2) . . ? C2 Re1 Br1 93.06(19) . . ? C3 Re1 Br1 177.3(2) . . ? N1 Re1 Br1 85.33(14) . . ? N2 Re1 Br1 83.25(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.17 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 4.960 _refine_diff_density_min -1.173 _refine_diff_density_rms 0.233 _database_code_depnum_ccdc_archive 'CCDC 929877' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H9 Br N2 O4 Re' _chemical_formula_weight 547.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 12.577(3) _cell_length_b 9.011(2) _cell_length_c 14.165(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.942(3) _cell_angle_gamma 90.00 _cell_volume 1581.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3169 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 25.94 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 10.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3724 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_process_details 'SADABS; Sheldrick, 2008 [Sheldrick, G. M. (2008)]' _exptl_special_details ; SADABS-2008 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1580 before and 0.0605 after correction. The estimated minimum and maximum transmission: 0.3724 0.7453. The l/2 correction factor is 0.0015. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11591 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_unetI/netI 0.0614 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.97 _reflns_number_total 3075 _reflns_number_gt 2471 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms were assigned ideal positions and refined isotropically as riding atoms. Due to disorder in the structure two parts were made, one to represent a particular position of the bromide ion (and the opposite carbonyl) as well as the hydroxide of the phenol ring on one of the meta positions. The other part was to represent the bromide located on the opposite axial position (again also parting out the corresponding carbonyl) and the hydroxide occupying the other meta position. These parts were assigned occupancies of 70% and 30% based on the intensity of their peaks on the difference map. ; _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^)+(0.2000P)^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 3075 _refine_ls_number_parameters 220 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1746 _refine_ls_wR_factor_gt 0.1518 _refine_ls_goodness_of_fit_ref 0.705 _refine_ls_restrained_S_all 0.705 _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 Br1 Br -0.07153(10) -0.06422(12) 0.84334(8) 0.0312(3) Uani 0.70 1 d P A 1 Br2 Br -0.0894(3) 0.4553(4) 0.7089(2) 0.0470(8) Uani 0.30 1 d P A 2 C1 C -0.0122(8) 0.1252(10) 0.6642(6) 0.037(2) Uani 1 1 d . A . C2 C -0.2211(8) 0.1357(9) 0.6814(6) 0.036(2) Uani 1 1 d . A . C3 C -0.0992(14) 0.3832(2) 0.7022(3) 0.0470(8) Uani 0.70 1 d PDU A 1 C4 C -0.2643(7) 0.2733(9) 0.8876(6) 0.030(2) Uani 1 1 d . . . H4 H -0.3144 0.2473 0.8339 0.036 Uiso 1 1 calc R . . C5 C -0.3002(8) 0.3225(9) 0.9697(7) 0.034(2) Uani 1 1 d . . . H5 H -0.3739 0.3320 0.9696 0.041 Uiso 1 1 calc R . . C6 C -0.2282(7) 0.3572(10) 1.0505(6) 0.032(2) Uani 1 1 d . . . H6 H -0.2521 0.3869 1.1062 0.038 Uiso 1 1 calc R . . C7 C -0.1200(7) 0.3470(10) 1.0477(6) 0.030(2) Uani 1 1 d . . . H7 H -0.0691 0.3715 1.1011 0.036 Uiso 1 1 calc R . . C8 C -0.0876(8) 0.2993(8) 0.9633(6) 0.027(2) Uani 1 1 d . . . C9 C 0.0256(7) 0.2883(8) 0.9541(6) 0.028(2) Uani 1 1 d . . . H9 H 0.0795 0.3080 1.0063 0.034 Uiso 1 1 calc R . . C10 C 0.1622(7) 0.2426(10) 0.8619(6) 0.0299(19) Uani 1 1 d . . . C11 C 0.2352(9) 0.1620(11) 0.9278(8) 0.046(3) Uani 1 1 d . E . H11 H 0.2134 0.1144 0.9795 0.055 Uiso 1 1 calc R . . C12 C 0.3417(9) 0.1553(14) 0.9134(9) 0.060(3) Uani 1 1 d . . . H12 H 0.3912 0.0981 0.9545 0.072 Uiso 0.70 1 calc PR B 1 C13 C 0.3752(9) 0.2305(14) 0.8407(9) 0.061(3) Uani 1 1 d . D . H13 H 0.4474 0.2272 0.8339 0.073 Uiso 1 1 calc R . . C14 C 0.3002(8) 0.3143(9) 0.7749(8) 0.042(3) Uani 1 1 d . . . H14 H 0.3226 0.3675 0.7257 0.050 Uiso 0.30 1 calc PR C 2 C15 C 0.1926(9) 0.3148(10) 0.7861(7) 0.041(3) Uani 1 1 d . D . H15 H 0.1414 0.3642 0.7420 0.050 Uiso 1 1 calc R . . C16 C -0.079(2) -0.0139(2) 0.7989(6) 0.0312(3) Uani 0.30 1 d PD A 2 N1 N -0.1598(6) 0.2627(7) 0.8847(5) 0.0254(16) Uani 1 1 d . A . N2 N 0.0499(6) 0.2507(7) 0.8725(5) 0.0263(16) Uani 1 1 d . A . O1 O 0.0329(5) 0.0843(7) 0.6030(4) 0.0427(17) Uani 1 1 d . . . O2 O -0.3021(6) 0.1005(7) 0.6359(5) 0.0499(19) Uani 1 1 d . . . O3 O -0.1053(9) 0.4952(4) 0.6626(5) 0.0470(8) Uani 0.70 1 d PDU A 1 O4 O 0.3306(11) 0.3950(15) 0.7059(10) 0.079(3) Uani 0.70 1 d PU D 1 O5 O 0.4210(19) 0.097(3) 0.9706(17) 0.048(4) Uani 0.30 1 d PU E 2 O6 O -0.0684(17) -0.1318(5) 0.8302(8) 0.0312(3) Uani 0.30 1 d PDU A 2 Re1 Re -0.08808(3) 0.19149(3) 0.762238(19) 0.02535(12) Uani 1 1 d 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 Br1 0.0381(6) 0.0277(6) 0.0265(6) 0.0045(5) 0.0014(5) 0.0016(5) Br2 0.0541(14) 0.0488(17) 0.0393(15) 0.0153(13) 0.0117(13) 0.0052(15) C1 0.049(5) 0.032(4) 0.028(5) 0.005(4) 0.001(4) 0.002(4) C2 0.056(6) 0.020(4) 0.030(5) 0.004(4) 0.000(4) 0.005(4) C3 0.0541(14) 0.0488(17) 0.0393(15) 0.0153(13) 0.0117(13) 0.0052(15) C4 0.031(4) 0.033(4) 0.024(4) 0.000(3) 0.001(4) -0.005(4) C5 0.033(5) 0.042(5) 0.028(5) 0.001(4) 0.005(4) -0.007(4) C6 0.038(5) 0.040(4) 0.016(4) -0.012(4) 0.004(3) -0.005(4) C7 0.033(5) 0.037(4) 0.019(4) 0.000(3) 0.000(4) -0.004(4) C8 0.037(5) 0.027(4) 0.014(4) -0.003(3) -0.006(3) 0.001(3) C9 0.034(5) 0.031(4) 0.019(4) 0.001(3) 0.002(4) 0.002(3) C10 0.030(4) 0.033(4) 0.026(4) -0.012(4) 0.002(3) -0.001(4) C11 0.048(6) 0.053(6) 0.037(5) -0.004(4) 0.007(5) 0.013(5) C12 0.042(6) 0.079(7) 0.056(7) -0.009(6) 0.002(5) 0.025(6) C13 0.038(6) 0.074(7) 0.071(8) -0.035(6) 0.011(6) 0.010(6) C14 0.045(5) 0.041(5) 0.048(6) -0.012(4) 0.031(5) -0.016(4) C15 0.048(6) 0.046(6) 0.032(5) -0.009(4) 0.014(4) -0.013(4) C16 0.0381(6) 0.0277(6) 0.0265(6) 0.0045(5) 0.0014(5) 0.0016(5) N1 0.034(4) 0.024(3) 0.017(3) 0.001(3) 0.001(3) -0.001(3) N2 0.039(4) 0.021(3) 0.017(3) -0.001(3) -0.004(3) -0.007(3) O1 0.050(4) 0.057(4) 0.022(3) -0.003(3) 0.010(3) 0.014(3) O2 0.056(4) 0.038(3) 0.042(4) -0.017(3) -0.028(3) 0.012(3) O3 0.0541(14) 0.0488(17) 0.0393(15) 0.0153(13) 0.0117(13) 0.0052(15) O4 0.080(5) 0.081(5) 0.078(5) -0.002(4) 0.018(4) -0.002(4) O5 0.044(5) 0.049(5) 0.049(6) 0.002(4) 0.005(4) 0.008(4) O6 0.0381(6) 0.0277(6) 0.0265(6) 0.0045(5) 0.0014(5) 0.0016(5) Re1 0.0340(2) 0.0306(2) 0.01095(19) -0.00044(11) 0.00249(15) -0.00044(13) _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 Br1 Re1 2.5671(12) . ? Br2 Re1 2.494(3) . ? C1 O1 1.174(11) . ? C1 Re1 1.912(10) . ? C2 O2 1.151(11) . ? C2 Re1 1.924(9) . ? C3 O3 1.150(2) . ? C3 Re1 1.9203(18) . ? C4 N1 1.326(11) . ? C4 C5 1.391(13) . ? C4 H4 0.9300 . ? C5 C6 1.368(12) . ? C5 H5 0.9300 . ? C6 C7 1.372(12) . ? C6 H6 0.9300 . ? C7 C8 1.396(12) . ? C7 H7 0.9300 . ? C8 N1 1.351(10) . ? C8 C9 1.455(13) . ? C9 N2 1.291(11) . ? C9 H9 0.9300 . ? C10 C15 1.365(13) . ? C10 C11 1.395(13) . ? C10 N2 1.448(11) . ? C11 C12 1.392(16) . ? C11 H11 0.9300 . ? C12 O5 1.28(2) . ? C12 C13 1.359(18) . ? C12 H12 0.9300 . ? C13 C14 1.423(16) . ? C13 H13 0.9300 . ? C14 O4 1.327(16) . ? C14 C15 1.389(15) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O6 1.150(2) . ? C16 Re1 1.9201(18) . ? N1 Re1 2.185(7) . ? N2 Re1 2.191(6) . ? 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 178.9(8) . . ? O2 C2 Re1 177.5(9) . . ? O3 C3 Re1 177.1(6) . . ? N1 C4 C5 121.0(8) . . ? N1 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 120.6(9) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 118.5(8) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C6 C7 C8 118.9(8) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? N1 C8 C7 121.8(8) . . ? N1 C8 C9 116.0(8) . . ? C7 C8 C9 122.2(8) . . ? N2 C9 C8 119.0(8) . . ? N2 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C15 C10 C11 122.2(9) . . ? C15 C10 N2 117.9(8) . . ? C11 C10 N2 119.9(8) . . ? C12 C11 C10 117.6(10) . . ? C12 C11 H11 121.2 . . ? C10 C11 H11 121.2 . . ? O5 C12 C13 112.0(15) . . ? O5 C12 C11 126.0(16) . . ? C13 C12 C11 121.4(11) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 120.3(10) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? O4 C14 C15 119.5(11) . . ? O4 C14 C13 122.0(11) . . ? C15 C14 C13 118.4(10) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? C10 C15 C14 119.9(10) . . ? C10 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? O6 C16 Re1 172.7(10) . . ? C4 N1 C8 119.1(7) . . ? C4 N1 Re1 126.4(5) . . ? C8 N1 Re1 114.5(6) . . ? C9 N2 C10 119.5(7) . . ? C9 N2 Re1 114.9(6) . . ? C10 N2 Re1 125.5(5) . . ? C1 Re1 C16 83.3(6) . . ? C1 Re1 C3 88.1(4) . . ? C16 Re1 C3 169.5(3) . . ? C1 Re1 C2 88.7(4) . . ? C16 Re1 C2 85.0(7) . . ? C3 Re1 C2 88.9(5) . . ? C1 Re1 N1 174.2(3) . . ? C16 Re1 N1 94.6(5) . . ? C3 Re1 N1 94.5(4) . . ? C2 Re1 N1 96.5(3) . . ? C1 Re1 N2 99.2(3) . . ? C16 Re1 N2 92.3(6) . . ? C3 Re1 N2 94.9(4) . . ? C2 Re1 N2 171.3(3) . . ? N1 Re1 N2 75.4(3) . . ? C1 Re1 Br2 93.2(3) . . ? C16 Re1 Br2 176.2(7) . . ? C3 Re1 Br2 8.8(2) . . ? C2 Re1 Br2 96.3(3) . . ? N1 Re1 Br2 88.77(19) . . ? N2 Re1 Br2 86.93(19) . . ? C1 Re1 Br1 91.9(3) . . ? C16 Re1 Br1 10.7(3) . . ? C3 Re1 Br1 179.5(5) . . ? C2 Re1 Br1 91.6(2) . . ? N1 Re1 Br1 85.47(18) . . ? N2 Re1 Br1 84.65(17) . . ? Br2 Re1 Br1 170.77(8) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.757 _refine_diff_density_min -1.714 _refine_diff_density_rms 0.216 _database_code_depnum_ccdc_archive 'CCDC 929878' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 Br N2 O4 Re' _chemical_formula_weight 549.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 13.186(3) _cell_length_b 8.966(2) _cell_length_c 13.615(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.260(3) _cell_angle_gamma 90.00 _cell_volume 1583.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4162 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.63 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1028 _exptl_absorpt_coefficient_mu 10.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6126 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_process_details 'SADABS; Sheldrick, 2008 [Sheldrick, G. M. (2008)]' _exptl_special_details ; SADABS V2008/1 (Bruker AXS) was used for absorption correction. wR2(int) was 0.0958 before and 0.0648 after correction. Estimated minimum and maximum transmission: 0.6126 0.7453. The \l/2 correction factor is 0.0015. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11654 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_unetI/netI 0.0636 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.66 _reflns_number_total 2998 _reflns_number_gt 2378 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms were assigned ideal positions and refined isotropically as riding atoms. Due to disorder in the structure two parts were made, one to represent a particular position of the bromide ion (and the opposite carbonyl) and the other part was to represent the bromide located on the opposite axial position (again also parting out the corresponding carbonyl). These parts were assigned occupancies of 65% and 35% based on the intensity of their peaks on the difference map. The hydroxyl group was also disordered over the two ortho positions of the phenyl ring. These were parted out at 75% and 25% occupancy based on the quality of the refinement. ; _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^)+(0.0000P)^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 2998 _refine_ls_number_parameters 246 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0706 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.209 _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 Br1 Br 0.41451(13) 0.4612(2) 0.20819(12) 0.0318(3) Uani 0.65 1 d P A 1 Br2 Br 0.4437(2) -0.0643(4) 0.3302(2) 0.0322(6) Uani 0.35 1 d PU A 2 C1 C 0.5020(6) 0.1378(9) 0.1522(6) 0.028(2) Uani 1 1 d . . . C2 C 0.3016(7) 0.1397(9) 0.1681(6) 0.031(2) Uani 1 1 d . . . C3 C 0.4363(13) -0.0220(5) 0.2932(11) 0.034(5) Uani 0.65 1 d PDU A 1 C4 C 0.2533(6) 0.2582(8) 0.3816(6) 0.0252(19) Uani 1 1 d . . . H4 H 0.2082 0.2337 0.3232 0.030 Uiso 1 1 calc R . . C5 C 0.2126(6) 0.2998(9) 0.4648(6) 0.0267(19) Uani 1 1 d . . . H5 H 0.1418 0.2999 0.4631 0.032 Uiso 1 1 calc R . . C6 C 0.2791(6) 0.3405(9) 0.5492(6) 0.029(2) Uani 1 1 d . . . H6 H 0.2536 0.3709 0.6054 0.035 Uiso 1 1 calc R . . C7 C 0.3831(6) 0.3368(9) 0.5513(6) 0.031(2) Uani 1 1 d . . . H7 H 0.4290 0.3639 0.6086 0.038 Uiso 1 1 calc R . . C8 C 0.4189(6) 0.2914(8) 0.4658(5) 0.0214(18) Uani 1 1 d . . . C9 C 0.5264(6) 0.2826(8) 0.4590(6) 0.0236(19) Uani 1 1 d . D . H9 H 0.5769 0.3022 0.5144 0.028 Uiso 1 1 calc R . . C10 C 0.6593(6) 0.2407(9) 0.3692(6) 0.0244(19) Uani 1 1 d . D . C11 C 0.6961(7) 0.3191(12) 0.2973(7) 0.044(3) Uani 1 1 d D . . H10 H 0.6499 0.3750 0.2523 0.053 Uiso 1 1 calc R B 1 C12 C 0.7975(8) 0.3196(14) 0.2884(8) 0.063(3) Uani 1 1 d . E . H11 H 0.8197 0.3782 0.2400 0.075 Uiso 1 1 calc R . . C13 C 0.8652(9) 0.2354(15) 0.3498(9) 0.073(4) Uani 1 1 d . . . H12 H 0.9339 0.2336 0.3422 0.087 Uiso 1 1 calc R E . C14 C 0.8343(8) 0.1515(14) 0.4239(8) 0.071(4) Uani 1 1 d . D . H13 H 0.8811 0.0943 0.4675 0.085 Uiso 1 1 calc R . . C15 C 0.7294(8) 0.1557(11) 0.4313(7) 0.049(3) Uani 1 1 d . . . H14 H 0.7068 0.0985 0.4802 0.058 Uiso 1 1 calc R C 2 C16 C 0.420(4) 0.3918(16) 0.209(3) 0.079(16) Uani 0.35 1 d PDU A 2 N1 N 0.3539(5) 0.2518(7) 0.3818(4) 0.0214(15) Uani 1 1 d . . . N2 N 0.5515(5) 0.2472(6) 0.3748(5) 0.0231(15) Uani 1 1 d . . . O1 O 0.5460(5) 0.1075(7) 0.0904(4) 0.0419(16) Uani 1 1 d . . . O2 O 0.2242(4) 0.1107(7) 0.1164(4) 0.0415(16) Uani 1 1 d . . . O3 O 0.4388(7) -0.1472(4) 0.3122(7) 0.036(3) Uani 0.65 1 d PDU A 1 O4 O 0.7000(8) 0.0807(10) 0.5068(8) 0.069(3) Uani 0.75 1 d P D 1 H4O H 0.6798 -0.0026 0.4875 0.103 Uiso 0.75 1 calc PR D 1 O5 O 0.4166(16) 0.5098(10) 0.1753(13) 0.034(6) Uani 0.35 1 d PDU A 2 O6 O 0.6482(17) 0.428(2) 0.2370(18) 0.059(8) Uani 0.25 1 d PD E 2 H6O H 0.5875 0.4060 0.2185 0.088 Uiso 0.25 1 calc PR E 2 Re1 Re 0.42583(2) 0.18737(4) 0.25650(2) 0.02495(11) Uani 1 1 d D A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0318(9) 0.0265(10) 0.0389(9) 0.0086(8) 0.0108(7) 0.0036(8) Br2 0.0299(12) 0.0291(13) 0.0365(14) 0.0004(12) 0.0026(11) 0.0000(11) C1 0.025(5) 0.033(5) 0.024(5) 0.000(4) 0.002(4) -0.002(4) C2 0.036(5) 0.028(5) 0.026(5) 0.000(4) -0.004(4) 0.007(4) C3 0.033(5) 0.035(5) 0.034(5) 0.000(2) 0.007(2) -0.001(2) C4 0.019(4) 0.025(5) 0.031(5) 0.003(4) 0.002(4) 0.001(3) C5 0.016(4) 0.028(5) 0.037(5) -0.002(4) 0.009(4) -0.005(4) C6 0.033(5) 0.036(5) 0.020(4) 0.000(4) 0.013(4) 0.002(4) C7 0.037(5) 0.035(5) 0.021(4) 0.000(4) 0.001(4) -0.003(4) C8 0.023(4) 0.019(4) 0.023(4) 0.001(4) 0.007(3) 0.001(4) C9 0.022(4) 0.023(5) 0.023(4) 0.000(4) -0.004(3) -0.006(4) C10 0.018(4) 0.033(5) 0.025(4) -0.008(4) 0.010(4) -0.002(4) C11 0.028(5) 0.067(7) 0.042(6) -0.033(6) 0.017(4) -0.024(5) C12 0.045(7) 0.094(9) 0.055(7) -0.045(7) 0.027(6) -0.032(7) C13 0.037(7) 0.121(12) 0.063(8) -0.050(8) 0.015(6) -0.002(7) C14 0.037(6) 0.116(11) 0.054(7) -0.030(7) -0.006(6) 0.048(7) C15 0.053(7) 0.053(7) 0.044(6) 0.011(5) 0.019(5) 0.009(5) C16 0.079(16) 0.079(16) 0.079(16) 0.000(2) 0.014(4) 0.000(2) N1 0.018(4) 0.026(4) 0.019(3) -0.002(3) 0.003(3) 0.000(3) N2 0.030(4) 0.013(3) 0.028(4) 0.000(3) 0.011(3) -0.002(3) O1 0.041(4) 0.057(4) 0.033(4) -0.008(3) 0.022(3) -0.005(3) O2 0.033(4) 0.046(4) 0.040(4) -0.006(3) -0.009(3) 0.007(3) O3 0.035(3) 0.035(3) 0.037(3) -0.0003(19) 0.0059(19) 0.000(2) O4 0.052(6) 0.048(6) 0.113(9) 0.026(6) 0.030(6) 0.011(5) O5 0.034(6) 0.034(6) 0.034(6) 0.000(2) 0.006(2) -0.001(2) O6 0.044(18) 0.07(2) 0.060(19) -0.005(17) 0.013(15) -0.040(16) Re1 0.01975(17) 0.0344(2) 0.02038(17) -0.00279(18) 0.00271(12) -0.00069(18) _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 Br1 Re1 2.539(2) . ? Br2 Re1 2.464(3) . ? C1 O1 1.137(9) . ? C1 Re1 1.931(9) . ? C2 O2 1.161(9) . ? C2 Re1 1.901(8) . ? C3 O3 1.151(2) . ? C3 Re1 1.942(2) . ? C4 N1 1.328(9) . ? C4 C5 1.389(10) . ? C4 H4 0.9300 . ? C5 C6 1.365(10) . ? C5 H5 0.9300 . ? C6 C7 1.368(11) . ? C6 H6 0.9300 . ? C7 C8 1.392(10) . ? C7 H7 0.9300 . ? C8 N1 1.349(9) . ? C8 C9 1.439(10) . ? C9 N2 1.288(9) . ? C9 H9 0.9300 . ? C10 C11 1.363(11) . ? C10 C15 1.368(11) . ? C10 N2 1.438(9) . ? C11 O6 1.358(2) . ? C11 C12 1.365(12) . ? C11 H10 0.9300 . ? C12 C13 1.341(15) . ? C12 H11 0.9300 . ? C13 C14 1.378(16) . ? C13 H12 0.9300 . ? C14 C15 1.405(13) . ? C14 H13 0.9300 . ? C15 O4 1.342(12) . ? C15 H14 0.9300 . ? C16 O5 1.151(2) . ? C16 Re1 1.941(2) . ? N1 Re1 2.172(6) . ? N2 Re1 2.163(6) . ? O4 H4O 0.8200 . ? O6 H6O 0.8200 . ? 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 179.2(8) . . ? O2 C2 Re1 178.0(8) . . ? O3 C3 Re1 177.2(14) . . ? N1 C4 C5 122.8(7) . . ? N1 C4 H4 118.6 . . ? C5 C4 H4 118.6 . . ? C6 C5 C4 118.4(7) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C7 120.1(7) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C8 118.6(7) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? N1 C8 C7 121.8(7) . . ? N1 C8 C9 114.5(7) . . ? C7 C8 C9 123.6(7) . . ? N2 C9 C8 118.9(7) . . ? N2 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C11 C10 C15 116.3(8) . . ? C11 C10 N2 119.9(7) . . ? C15 C10 N2 123.7(8) . . ? O6 C11 C10 128.3(14) . . ? O6 C11 C12 107.5(15) . . ? C10 C11 C12 123.1(11) . . ? C10 C11 H10 118.5 . . ? C12 C11 H10 118.5 . . ? C13 C12 C11 119.8(12) . . ? C13 C12 H11 120.1 . . ? C11 C12 H11 120.1 . . ? C12 C13 C14 120.9(11) . . ? C12 C13 H12 119.6 . . ? C14 C13 H12 119.6 . . ? C13 C14 C15 117.5(10) . . ? C13 C14 H13 121.3 . . ? C15 C14 H13 121.3 . . ? O4 C15 C10 119.8(10) . . ? O4 C15 C14 117.6(10) . . ? C10 C15 C14 122.4(10) . . ? C10 C15 H14 118.8 . . ? C14 C15 H14 118.8 . . ? O5 C16 Re1 176(4) . . ? C4 N1 C8 118.3(7) . . ? C4 N1 Re1 125.9(5) . . ? C8 N1 Re1 115.8(5) . . ? C9 N2 C10 118.1(7) . . ? C9 N2 Re1 116.1(5) . . ? C10 N2 Re1 125.7(5) . . ? C15 O4 H4O 109.5 . . ? C11 O6 H6O 109.5 . . ? C2 Re1 C1 89.2(3) . . ? C2 Re1 C16 91.4(13) . . ? C1 Re1 C16 88.0(14) . . ? C2 Re1 C3 87.7(5) . . ? C1 Re1 C3 86.8(5) . . ? C16 Re1 C3 174.8(14) . . ? C2 Re1 N2 170.8(3) . . ? C1 Re1 N2 100.1(3) . . ? C16 Re1 N2 89.6(13) . . ? C3 Re1 N2 92.2(5) . . ? C2 Re1 N1 96.3(3) . . ? C1 Re1 N1 174.5(3) . . ? C16 Re1 N1 90.9(13) . . ? C3 Re1 N1 94.4(5) . . ? N2 Re1 N1 74.5(2) . . ? C2 Re1 Br2 93.5(2) . . ? C1 Re1 Br2 93.7(2) . . ? C16 Re1 Br2 174.8(13) . . ? C3 Re1 Br2 9.0(5) . . ? N2 Re1 Br2 85.33(17) . . ? N1 Re1 Br2 86.97(17) . . ? C2 Re1 Br1 92.8(2) . . ? C1 Re1 Br1 92.7(2) . . ? C16 Re1 Br1 4.8(13) . . ? C3 Re1 Br1 179.3(5) . . ? N2 Re1 Br1 87.42(16) . . ? N1 Re1 Br1 86.13(16) . . ? Br2 Re1 Br1 171.10(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.511 _refine_diff_density_min -0.927 _refine_diff_density_rms 0.198 _database_code_depnum_ccdc_archive 'CCDC 929879'