# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Majid Motevalli' _publ_contact_author_email m.motevalli@qmul.ac.uk loop_ _publ_author_name 'D.Vaughan Griffiths' 'Yuen-Ki Cheong' 'Philip Duncanson' 'Majid Motevalli' data_pd-9-56r _database_code_depnum_ccdc_archive 'CCDC 733190' #TrackingRef '- 3c_CCDC733190.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 Br N4 O5 Re' _chemical_formula_weight 672.50 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' Br Br -0.2901 2.4595 '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' Re Re -1.0185 7.2310 '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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_Int_Tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 29.8269(16) _cell_length_b 29.8269(16) _cell_length_c 15.6504(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 12057.9(12) _cell_formula_units_Z 18 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 100431 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5796 _exptl_absorpt_coefficient_mu 6.060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5553 _exptl_absorpt_correction_T_max 0.7936 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 19587 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.67 _reflns_number_total 5025 _reflns_number_gt 3987 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'DIRDIF08 (Beurskens et al, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+1088.8053P] 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 5025 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0820 _refine_ls_wR_factor_ref 0.1822 _refine_ls_wR_factor_gt 0.1731 _refine_ls_goodness_of_fit_ref 1.211 _refine_ls_restrained_S_all 1.211 _refine_ls_shift/su_max 0.003 _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 0.1691(6) -0.0351(6) 0.5797(9) 0.033(3) Uani 1 1 d . . . C2 C 0.2150(7) 0.0319(7) 0.7070(12) 0.051(4) Uani 1 1 d . . . C3 C 0.1604(7) 0.0498(6) 0.5892(11) 0.043(4) Uani 1 1 d . . . C4 C 0.3181(6) 0.0997(7) 0.4614(10) 0.042(4) Uani 1 1 d . . . C5 C 0.3214(6) 0.0563(7) 0.5089(10) 0.044(4) Uani 1 1 d . . . C6 C 0.3569(7) 0.0408(9) 0.4856(12) 0.064(6) Uani 1 1 d . . . H6 H 0.3811 0.0587 0.4413 0.077 Uiso 1 1 calc R . . C7 C 0.3569(6) -0.0006(8) 0.5267(11) 0.051(5) Uani 1 1 d . . . H7 H 0.3810 -0.0111 0.5105 0.062 Uiso 1 1 calc R . . C8 C 0.3217(7) -0.0264(8) 0.5909(12) 0.056(5) Uani 1 1 d . . . H8 H 0.3219 -0.0537 0.6218 0.067 Uiso 1 1 calc R . . C9 C 0.2865(6) -0.0111(5) 0.6085(10) 0.034(3) Uani 1 1 d . . . H9 H 0.2607 -0.0302 0.6502 0.040 Uiso 1 1 calc R . . C10 C 0.2705(5) 0.0721(6) 0.4032(10) 0.034(3) Uani 1 1 d . . . C11 C 0.2731(7) 0.0762(6) 0.3147(11) 0.044(4) Uani 1 1 d . . . H11 H 0.3053 0.0962 0.2864 0.052 Uiso 1 1 calc R . . C12 C 0.2271(7) 0.0501(6) 0.2687(11) 0.047(4) Uani 1 1 d . . . H12 H 0.2278 0.0521 0.2081 0.057 Uiso 1 1 calc R . . C13 C 0.1815(6) 0.0221(6) 0.3098(11) 0.043(4) Uani 1 1 d . . . H13 H 0.1501 0.0044 0.2784 0.052 Uiso 1 1 calc R . . C14 C 0.1810(6) 0.0196(5) 0.3970(10) 0.037(3) Uani 1 1 d . . . H14 H 0.1488 -0.0004 0.4254 0.044 Uiso 1 1 calc R . . C15 C 0.4136(7) 0.1551(8) 0.4489(15) 0.078(8) Uani 1 1 d . . . C16 C 0.4574(19) 0.196(2) 0.396(3) 0.073(13) Uani 0.53(5) 1 d P A 1 H16A H 0.4577 0.2288 0.4015 0.110 Uiso 0.53(5) 1 calc PR A 1 H16B H 0.4526 0.1852 0.3363 0.110 Uiso 0.53(5) 1 calc PR A 1 H16C H 0.4904 0.2003 0.4170 0.110 Uiso 0.53(5) 1 calc PR A 1 C16' C 0.456(2) 0.167(3) 0.382(4) 0.073(13) Uani 0.47(5) 1 d P A 2 H16D H 0.4523 0.1343 0.3606 0.110 Uiso 0.47(5) 1 calc PR A 2 H16E H 0.4903 0.1873 0.4088 0.110 Uiso 0.47(5) 1 calc PR A 2 H16F H 0.4529 0.1864 0.3347 0.110 Uiso 0.47(5) 1 calc PR A 2 C17 C 0.3116(7) 0.1369(6) 0.5189(10) 0.047(4) Uani 1 1 d . . . C18 C 0.3388(7) 0.1912(8) 0.5028(14) 0.067(6) Uani 1 1 d . . . H18 H 0.3634 0.2052 0.4578 0.081 Uiso 1 1 calc R . . C19 C 0.3287(9) 0.2238(7) 0.5548(17) 0.078(8) Uani 1 1 d . . . H19 H 0.3461 0.2600 0.5439 0.093 Uiso 1 1 calc R . . C20 C 0.2952(8) 0.2046(6) 0.6187(15) 0.061(6) Uani 1 1 d . . . H20 H 0.2901 0.2271 0.6555 0.073 Uiso 1 1 calc R . . C21 C 0.2677(7) 0.1516(6) 0.6315(11) 0.049(4) Uani 1 1 d . . . H21 H 0.2440 0.1378 0.6779 0.058 Uiso 1 1 calc R . . Br1 Br 0.47397(15) 0.03049(16) 0.3953(2) 0.0600(7) Uani 0.527(3) 1 d P B 1 Br1' Br 0.47925(16) 0.07935(18) 0.3661(3) 0.0600(7) Uani 0.473(3) 1 d P B 2 N1 N 0.2741(4) 0.1189(4) 0.5784(8) 0.029(3) Uani 1 1 d . . . N2 N 0.2249(5) 0.0446(4) 0.4443(8) 0.035(3) Uani 1 1 d . . . N3 N 0.2854(5) 0.0285(5) 0.5718(8) 0.039(3) Uani 1 1 d . . . N4 N 0.3649(5) 0.1279(7) 0.4119(9) 0.062(5) Uani 1 1 d . A . H4A H 0.3625 0.1278 0.3559 0.075 Uiso 1 1 calc R . . Re1 Re 0.21771(2) 0.03701(2) 0.58457(4) 0.03346(19) Uani 1 1 d . . . O2 O 0.2118(6) 0.0282(6) 0.7788(8) 0.068(4) Uani 1 1 d . . . O1 O 0.1392(4) -0.0794(4) 0.5790(8) 0.050(3) Uani 1 1 d . . . O3 O 0.1259(5) 0.0562(5) 0.5915(10) 0.063(4) Uani 1 1 d . . . O4 O 0.4178(4) 0.1527(5) 0.5262(9) 0.063(4) Uani 1 1 d . A . O5 O 0.5647(9) 0.0521(9) 0.447(2) 0.097(8) Uani 0.63(2) 1 d P C 1 O5' O 0.4293(16) -0.0404(15) 0.433(4) 0.097(8) Uani 0.37(2) 1 d P C 2 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 0.031(8) 0.041(9) 0.032(8) -0.003(7) 0.000(6) 0.022(7) C2 0.052(11) 0.044(10) 0.043(10) -0.001(8) -0.007(9) 0.015(8) C3 0.046(10) 0.025(8) 0.044(10) 0.002(7) 0.001(8) 0.008(7) C4 0.030(8) 0.058(10) 0.033(9) 0.009(8) 0.000(7) 0.019(8) C5 0.042(9) 0.052(10) 0.028(8) 0.011(7) -0.007(7) 0.015(8) C6 0.031(9) 0.094(16) 0.052(12) 0.009(11) 0.009(8) 0.020(10) C7 0.040(9) 0.085(14) 0.041(10) -0.007(10) -0.012(8) 0.041(10) C8 0.051(11) 0.063(12) 0.056(12) -0.004(10) -0.015(9) 0.031(10) C9 0.034(8) 0.026(7) 0.039(9) -0.001(6) 0.000(7) 0.013(6) C10 0.026(7) 0.033(8) 0.045(9) 0.001(7) -0.006(7) 0.017(7) C11 0.048(10) 0.041(9) 0.043(10) 0.000(7) 0.005(8) 0.022(8) C12 0.060(11) 0.039(9) 0.042(10) -0.011(7) -0.002(8) 0.024(9) C13 0.042(9) 0.033(8) 0.054(11) 0.000(8) -0.004(8) 0.018(7) C14 0.033(8) 0.029(8) 0.048(10) -0.009(7) -0.010(7) 0.015(7) C15 0.035(10) 0.070(14) 0.076(15) 0.038(12) -0.019(10) -0.014(9) C16 0.064(16) 0.12(4) 0.07(2) 0.04(3) 0.006(15) 0.07(3) C16' 0.064(16) 0.12(4) 0.07(2) 0.04(3) 0.006(15) 0.07(3) C17 0.048(10) 0.037(9) 0.034(9) 0.011(7) -0.011(8) 0.005(8) C18 0.038(10) 0.047(11) 0.072(14) 0.021(10) -0.023(9) -0.012(9) C19 0.073(15) 0.030(10) 0.099(18) 0.009(12) -0.057(14) 0.003(10) C20 0.061(12) 0.026(9) 0.090(16) -0.013(10) -0.048(12) 0.018(9) C21 0.056(11) 0.034(9) 0.047(10) -0.002(8) -0.021(8) 0.016(8) Br1 0.0628(17) 0.0832(19) 0.0410(15) -0.0079(13) 0.0056(12) 0.0419(16) Br1' 0.0628(17) 0.0832(19) 0.0410(15) -0.0079(13) 0.0056(12) 0.0419(16) N1 0.029(6) 0.023(6) 0.036(7) 0.000(5) -0.008(5) 0.014(5) N2 0.033(7) 0.029(6) 0.048(8) -0.008(6) -0.010(6) 0.021(6) N3 0.026(6) 0.057(8) 0.036(7) 0.008(6) 0.000(5) 0.022(6) N4 0.034(8) 0.094(12) 0.034(8) 0.023(8) -0.001(6) 0.014(8) Re1 0.0326(3) 0.0266(3) 0.0376(3) -0.0012(3) 0.0010(3) 0.0121(3) O2 0.076(10) 0.078(10) 0.044(8) 0.008(7) 0.006(7) 0.033(8) O1 0.043(7) 0.035(6) 0.060(8) -0.007(6) 0.002(6) 0.009(5) O3 0.043(7) 0.048(7) 0.108(12) -0.004(7) 0.008(7) 0.031(6) O4 0.034(6) 0.076(9) 0.062(9) 0.018(7) -0.011(6) 0.015(6) O5 0.071(13) 0.059(12) 0.18(2) 0.012(14) 0.033(16) 0.045(11) O5' 0.071(13) 0.059(12) 0.18(2) 0.012(14) 0.033(16) 0.045(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.168(18) . ? C1 Re1 1.902(15) . ? C2 O2 1.13(2) . ? C2 Re1 1.921(18) . ? C3 O3 1.14(2) . ? C3 Re1 1.930(18) . ? C4 N4 1.44(2) . ? C4 C17 1.51(2) . ? C4 C10 1.53(2) . ? C4 C5 1.54(2) . ? C5 N3 1.386(19) . ? C5 C6 1.40(3) . ? C6 C7 1.39(3) . ? C6 H6 0.9500 . ? C7 C8 1.38(3) . ? C7 H7 0.9500 . ? C8 C9 1.37(2) . ? C8 H8 0.9500 . ? C9 N3 1.327(19) . ? C9 H9 0.9500 . ? C10 N2 1.350(19) . ? C10 C11 1.39(2) . ? C11 C12 1.39(2) . ? C11 H11 0.9500 . ? C12 C13 1.35(2) . ? C12 H12 0.9500 . ? C13 C14 1.37(2) . ? C13 H13 0.9500 . ? C14 N2 1.357(18) . ? C14 H14 0.9500 . ? C15 O4 1.22(2) . ? C15 N4 1.39(2) . ? C15 C16 1.51(5) . ? C15 C16' 1.54(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16' H16D 0.9800 . ? C16' H16E 0.9800 . ? C16' H16F 0.9800 . ? C17 N1 1.34(2) . ? C17 C18 1.42(2) . ? C18 C19 1.41(3) . ? C18 H18 0.9500 . ? C19 C20 1.32(3) . ? C19 H19 0.9500 . ? C20 C21 1.38(2) . ? C20 H20 0.9500 . ? C21 N1 1.37(2) . ? C21 H21 0.9500 . ? N1 Re1 2.168(11) . ? N2 Re1 2.207(13) . ? N3 Re1 2.166(12) . ? N4 H4A 0.8800 . ? 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 178.3(13) . . ? O2 C2 Re1 177.9(17) . . ? O3 C3 Re1 178.6(14) . . ? N4 C4 C17 109.5(15) . . ? N4 C4 C10 111.1(13) . . ? C17 C4 C10 108.8(13) . . ? N4 C4 C5 107.3(13) . . ? C17 C4 C5 114.5(13) . . ? C10 C4 C5 105.5(13) . . ? N3 C5 C6 118.4(16) . . ? N3 C5 C4 119.3(15) . . ? C6 C5 C4 122.0(15) . . ? C7 C6 C5 120.6(16) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C6 119.6(17) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 117.4(17) . . ? C7 C8 H8 121.3 . . ? C9 C8 H8 121.3 . . ? N3 C9 C8 125.1(15) . . ? N3 C9 H9 117.5 . . ? C8 C9 H9 117.5 . . ? N2 C10 C11 121.6(14) . . ? N2 C10 C4 115.1(13) . . ? C11 C10 C4 123.3(14) . . ? C10 C11 C12 118.0(15) . . ? C10 C11 H11 121.0 . . ? C12 C11 H11 121.0 . . ? C13 C12 C11 120.4(17) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.3(16) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? N2 C14 C13 122.3(15) . . ? N2 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? O4 C15 N4 119.1(17) . . ? O4 C15 C16 121(3) . . ? N4 C15 C16 118(2) . . ? O4 C15 C16' 126(3) . . ? N4 C15 C16' 111(3) . . ? C16 C15 C16' 33(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? C15 C16' H16D 109.5 . . ? C15 C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? C15 C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? N1 C17 C18 117.6(18) . . ? N1 C17 C4 120.4(13) . . ? C18 C17 C4 121.2(17) . . ? C19 C18 C17 119(2) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C20 C19 C18 120.8(18) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 120(2) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? N1 C21 C20 120.8(19) . . ? N1 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C17 N1 C21 121.5(13) . . ? C17 N1 Re1 120.1(10) . . ? C21 N1 Re1 118.1(10) . . ? C14 N2 C10 118.5(14) . . ? C14 N2 Re1 118.0(11) . . ? C10 N2 Re1 123.5(10) . . ? C9 N3 C5 118.9(13) . . ? C9 N3 Re1 120.2(10) . . ? C5 N3 Re1 119.0(10) . . ? C15 N4 C4 122.8(15) . . ? C15 N4 H4A 118.6 . . ? C4 N4 H4A 118.6 . . ? C2 Re1 C1 88.4(7) . . ? C2 Re1 C3 88.4(8) . . ? C1 Re1 C3 88.6(6) . . ? C2 Re1 N3 95.0(7) . . ? C1 Re1 N3 95.3(5) . . ? C3 Re1 N3 174.9(6) . . ? C2 Re1 N1 96.4(6) . . ? C1 Re1 N1 175.1(5) . . ? C3 Re1 N1 92.5(5) . . ? N3 Re1 N1 83.4(5) . . ? C2 Re1 N2 177.3(6) . . ? C1 Re1 N2 93.2(5) . . ? C3 Re1 N2 93.8(6) . . ? N3 Re1 N2 82.7(4) . . ? N1 Re1 N2 81.9(4) . . ? 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 N4 C4 C5 N3 169.7(14) . . . . ? C17 C4 C5 N3 48(2) . . . . ? C10 C4 C5 N3 -71.8(18) . . . . ? N4 C4 C5 C6 -16(2) . . . . ? C17 C4 C5 C6 -138.0(17) . . . . ? C10 C4 C5 C6 102.3(18) . . . . ? N3 C5 C6 C7 -2(3) . . . . ? C4 C5 C6 C7 -176.2(16) . . . . ? C5 C6 C7 C8 0(3) . . . . ? C6 C7 C8 C9 3(3) . . . . ? C7 C8 C9 N3 -4(3) . . . . ? N4 C4 C10 N2 179.7(14) . . . . ? C17 C4 C10 N2 -59.6(17) . . . . ? C5 C4 C10 N2 63.8(17) . . . . ? N4 C4 C10 C11 -3(2) . . . . ? C17 C4 C10 C11 118.1(16) . . . . ? C5 C4 C10 C11 -118.5(16) . . . . ? N2 C10 C11 C12 -1(2) . . . . ? C4 C10 C11 C12 -178.7(15) . . . . ? C10 C11 C12 C13 0(2) . . . . ? C11 C12 C13 C14 0(2) . . . . ? C12 C13 C14 N2 1(2) . . . . ? N4 C4 C17 N1 -171.9(13) . . . . ? C10 C4 C17 N1 66.4(18) . . . . ? C5 C4 C17 N1 -51(2) . . . . ? N4 C4 C17 C18 18(2) . . . . ? C10 C4 C17 C18 -103.3(18) . . . . ? C5 C4 C17 C18 138.9(16) . . . . ? N1 C17 C18 C19 6(2) . . . . ? C4 C17 C18 C19 175.7(16) . . . . ? C17 C18 C19 C20 1(3) . . . . ? C18 C19 C20 C21 -4(3) . . . . ? C19 C20 C21 N1 -1(3) . . . . ? C18 C17 N1 C21 -10(2) . . . . ? C4 C17 N1 C21 179.4(13) . . . . ? C18 C17 N1 Re1 163.9(11) . . . . ? C4 C17 N1 Re1 -6.1(19) . . . . ? C20 C21 N1 C17 8(2) . . . . ? C20 C21 N1 Re1 -166.2(12) . . . . ? C13 C14 N2 C10 -1(2) . . . . ? C13 C14 N2 Re1 179.7(11) . . . . ? C11 C10 N2 C14 2(2) . . . . ? C4 C10 N2 C14 179.2(13) . . . . ? C11 C10 N2 Re1 -179.4(11) . . . . ? C4 C10 N2 Re1 -1.7(17) . . . . ? C8 C9 N3 C5 2(2) . . . . ? C8 C9 N3 Re1 165.8(13) . . . . ? C6 C5 N3 C9 1(2) . . . . ? C4 C5 N3 C9 175.6(14) . . . . ? C6 C5 N3 Re1 -162.9(13) . . . . ? C4 C5 N3 Re1 11.4(19) . . . . ? O4 C15 N4 C4 5(4) . . . . ? C16 C15 N4 C4 -161(3) . . . . ? C16' C15 N4 C4 163(3) . . . . ? C17 C4 N4 C15 62(2) . . . . ? C10 C4 N4 C15 -178.2(19) . . . . ? C5 C4 N4 C15 -63(2) . . . . ? O2 C2 Re1 C1 -54(46) . . . . ? O2 C2 Re1 C3 35(46) . . . . ? O2 C2 Re1 N3 -149(46) . . . . ? O2 C2 Re1 N1 127(46) . . . . ? O2 C2 Re1 N2 180(100) . . . . ? O1 C1 Re1 C2 5(41) . . . . ? O1 C1 Re1 C3 -84(41) . . . . ? O1 C1 Re1 N3 99(41) . . . . ? O1 C1 Re1 N1 173(100) . . . . ? O1 C1 Re1 N2 -178(100) . . . . ? O3 C3 Re1 C2 -100(66) . . . . ? O3 C3 Re1 C1 -12(66) . . . . ? O3 C3 Re1 N3 128(63) . . . . ? O3 C3 Re1 N1 163(66) . . . . ? O3 C3 Re1 N2 81(66) . . . . ? C9 N3 Re1 C2 52.3(13) . . . . ? C5 N3 Re1 C2 -143.8(13) . . . . ? C9 N3 Re1 C1 -36.6(12) . . . . ? C5 N3 Re1 C1 127.4(12) . . . . ? C9 N3 Re1 C3 -176(6) . . . . ? C5 N3 Re1 C3 -12(7) . . . . ? C9 N3 Re1 N1 148.2(12) . . . . ? C5 N3 Re1 N1 -47.9(12) . . . . ? C9 N3 Re1 N2 -129.2(12) . . . . ? C5 N3 Re1 N2 34.8(12) . . . . ? C17 N1 Re1 C2 140.3(12) . . . . ? C21 N1 Re1 C2 -45.1(12) . . . . ? C17 N1 Re1 C1 -28(6) . . . . ? C21 N1 Re1 C1 146(6) . . . . ? C17 N1 Re1 C3 -131.0(12) . . . . ? C21 N1 Re1 C3 43.6(11) . . . . ? C17 N1 Re1 N3 46.0(11) . . . . ? C21 N1 Re1 N3 -139.4(11) . . . . ? C17 N1 Re1 N2 -37.5(11) . . . . ? C21 N1 Re1 N2 137.1(11) . . . . ? C14 N2 Re1 C2 169(13) . . . . ? C10 N2 Re1 C2 -11(14) . . . . ? C14 N2 Re1 C1 42.5(11) . . . . ? C10 N2 Re1 C1 -136.6(11) . . . . ? C14 N2 Re1 C3 -46.3(11) . . . . ? C10 N2 Re1 C3 134.6(11) . . . . ? C14 N2 Re1 N3 137.4(11) . . . . ? C10 N2 Re1 N3 -41.7(11) . . . . ? C14 N2 Re1 N1 -138.3(10) . . . . ? C10 N2 Re1 N1 42.6(11) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.67 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.877 _refine_diff_density_min -1.852 _refine_diff_density_rms 0.231 # Attachment '- 8c_CCDC821715.cif' data_kycp15a _database_code_depnum_ccdc_archive 'CCDC 821715' #TrackingRef '- 8c_CCDC821715.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 N3 O4 Re' _chemical_formula_weight 496.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.65980(10) _cell_length_b 8.71430(10) _cell_length_c 11.5640(2) _cell_angle_alpha 77.8700(10) _cell_angle_beta 88.8620(10) _cell_angle_gamma 70.1920(10) _cell_volume 801.452(19) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10302 _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.057 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 7.606 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.0643 _exptl_absorpt_correction_T_max 0.2246 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_reflns_number 18270 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3673 _reflns_number_gt 3620 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'DIRDIF08 (Beurskens et al, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0033P)^2^+1.1971P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0192(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3673 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0166 _refine_ls_R_factor_gt 0.0162 _refine_ls_wR_factor_ref 0.0390 _refine_ls_wR_factor_gt 0.0388 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _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 C1 C 0.0684(3) 0.0052(3) 0.1673(2) 0.0164(5) Uani 1 1 d . . . C2 C -0.0076(4) 0.1749(4) 0.3463(3) 0.0197(6) Uani 1 1 d . . . C3 C -0.0442(3) 0.3384(3) 0.1157(3) 0.0181(6) Uani 1 1 d . . . C4 C 0.4291(3) 0.2467(3) 0.2438(2) 0.0102(5) Uani 1 1 d . . . H4 H 0.5005 0.3076 0.2641 0.012 Uiso 1 1 calc R . . C5 C 0.4796(3) 0.0693(3) 0.3164(2) 0.0100(5) Uani 1 1 d . . . C6 C 0.6324(3) -0.0202(3) 0.3734(2) 0.0129(5) Uani 1 1 d . . . H6 H 0.7154 0.0289 0.3702 0.015 Uiso 1 1 calc R . . C7 C 0.6625(3) -0.1836(3) 0.4356(2) 0.0157(5) Uani 1 1 d . . . H7 H 0.7657 -0.2469 0.4768 0.019 Uiso 1 1 calc R . . C8 C 0.5397(3) -0.2528(3) 0.4366(2) 0.0153(5) Uani 1 1 d . . . H8 H 0.5581 -0.3645 0.4778 0.018 Uiso 1 1 calc R . . C9 C 0.3900(3) -0.1570(3) 0.3769(2) 0.0128(5) Uani 1 1 d . . . H9 H 0.3061 -0.2045 0.3777 0.015 Uiso 1 1 calc R . . C10 C 0.4331(3) 0.2379(3) 0.1144(2) 0.0099(5) Uani 1 1 d . . . C11 C 0.5454(3) 0.2743(3) 0.0363(2) 0.0140(5) Uani 1 1 d . . . H11 H 0.6318 0.3049 0.0628 0.017 Uiso 1 1 calc R . . C12 C 0.5303(3) 0.2657(3) -0.0813(2) 0.0175(6) Uani 1 1 d . . . H12 H 0.6042 0.2928 -0.1370 0.021 Uiso 1 1 calc R . . C13 C 0.4051(4) 0.2166(3) -0.1155(2) 0.0172(5) Uani 1 1 d . . . H13 H 0.3927 0.2086 -0.1952 0.021 Uiso 1 1 calc R . . C14 C 0.2979(3) 0.1792(3) -0.0328(2) 0.0140(5) Uani 1 1 d . . . H14 H 0.2132 0.1443 -0.0568 0.017 Uiso 1 1 calc R . . C15 C 0.2155(3) 0.4757(3) 0.2983(2) 0.0113(5) Uani 1 1 d . . . C16 C 0.0361(3) 0.5590(3) 0.3180(3) 0.0184(6) Uani 1 1 d . . . H16A H 0.0224 0.6595 0.3483 0.028 Uiso 1 1 calc R . . H16B H -0.0018 0.4815 0.3756 0.028 Uiso 1 1 calc R . . H16C H -0.0287 0.5900 0.2428 0.028 Uiso 1 1 calc R . . N1 N 0.2552(3) 0.3292(3) 0.26535(19) 0.0109(4) Uani 1 1 d . . . N2 N 0.3106(3) 0.1910(2) 0.07996(18) 0.0094(4) Uani 1 1 d . . . N3 N 0.3600(3) 0.0014(3) 0.31773(18) 0.0093(4) Uani 1 1 d . . . O1 O 0.0286(3) -0.0934(3) 0.1359(2) 0.0270(5) Uani 1 1 d . . . O2 O -0.0932(3) 0.1803(3) 0.4239(2) 0.0356(6) Uani 1 1 d . . . O3 O -0.1505(3) 0.4350(3) 0.0527(2) 0.0290(5) Uani 1 1 d . . . O4 O 0.3166(2) 0.5439(2) 0.31426(17) 0.0177(4) Uani 1 1 d . . . Re1 Re 0.134395(11) 0.172997(10) 0.216650(8) 0.00952(5) 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(14) 0.0155(12) 0.0162(13) 0.0029(10) -0.0031(10) -0.0070(11) C2 0.0178(14) 0.0214(14) 0.0252(15) -0.0076(11) 0.0054(11) -0.0121(11) C3 0.0151(14) 0.0142(12) 0.0292(15) -0.0054(11) 0.0033(11) -0.0101(11) C4 0.0088(12) 0.0111(11) 0.0137(12) -0.0066(9) 0.0016(9) -0.0048(9) C5 0.0133(12) 0.0118(11) 0.0074(11) -0.0070(9) 0.0028(9) -0.0045(10) C6 0.0126(13) 0.0182(12) 0.0096(12) -0.0079(10) 0.0020(9) -0.0049(10) C7 0.0161(13) 0.0192(13) 0.0072(12) -0.0045(10) -0.0014(10) 0.0007(10) C8 0.0240(14) 0.0123(12) 0.0074(11) -0.0020(9) 0.0014(10) -0.0033(10) C9 0.0209(14) 0.0115(11) 0.0081(11) -0.0040(9) 0.0030(10) -0.0071(10) C10 0.0113(12) 0.0059(10) 0.0116(12) -0.0018(9) -0.0002(9) -0.0017(9) C11 0.0122(13) 0.0122(12) 0.0181(13) -0.0038(10) 0.0039(10) -0.0046(10) C12 0.0186(14) 0.0135(12) 0.0169(13) -0.0017(10) 0.0093(10) -0.0026(10) C13 0.0237(15) 0.0139(12) 0.0098(12) -0.0025(10) 0.0012(10) -0.0011(11) C14 0.0163(14) 0.0097(11) 0.0150(13) -0.0028(9) -0.0014(10) -0.0029(10) C15 0.0180(13) 0.0091(11) 0.0069(11) -0.0013(9) 0.0026(9) -0.0050(10) C16 0.0209(15) 0.0125(12) 0.0210(14) -0.0066(10) 0.0068(11) -0.0031(11) N1 0.0110(11) 0.0113(10) 0.0127(10) -0.0051(8) 0.0036(8) -0.0053(8) N2 0.0101(10) 0.0078(9) 0.0097(10) -0.0018(8) 0.0005(8) -0.0022(8) N3 0.0136(11) 0.0096(9) 0.0066(10) -0.0041(8) 0.0006(8) -0.0050(8) O1 0.0364(13) 0.0201(10) 0.0299(12) -0.0003(9) -0.0121(10) -0.0189(10) O2 0.0358(14) 0.0456(14) 0.0374(14) -0.0168(11) 0.0245(11) -0.0259(12) O3 0.0175(11) 0.0168(10) 0.0459(14) 0.0056(9) -0.0098(10) -0.0040(9) O4 0.0229(11) 0.0114(9) 0.0220(10) -0.0069(7) 0.0011(8) -0.0080(8) Re1 0.00913(7) 0.00930(7) 0.01181(7) -0.00247(4) 0.00093(4) -0.00519(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.151(3) . ? C1 Re1 1.929(3) . ? C2 O2 1.151(4) . ? C2 Re1 1.919(3) . ? C3 O3 1.153(4) . ? C3 Re1 1.920(3) . ? C4 N1 1.474(3) . ? C4 C10 1.514(3) . ? C4 C5 1.516(3) . ? C4 H4 1.0000 . ? C5 N3 1.354(3) . ? C5 C6 1.383(4) . ? C6 C7 1.392(4) . ? C6 H6 0.9500 . ? C7 C8 1.388(4) . ? C7 H7 0.9500 . ? C8 C9 1.383(4) . ? C8 H8 0.9500 . ? C9 N3 1.345(3) . ? C9 H9 0.9500 . ? C10 N2 1.353(3) . ? C10 C11 1.384(3) . ? C11 C12 1.389(4) . ? C11 H11 0.9500 . ? C12 C13 1.384(4) . ? C12 H12 0.9500 . ? C13 C14 1.386(4) . ? C13 H13 0.9500 . ? C14 N2 1.338(3) . ? C14 H14 0.9500 . ? C15 O4 1.249(3) . ? C15 N1 1.340(3) . ? C15 C16 1.511(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 Re1 2.139(2) . ? N2 Re1 2.194(2) . ? N3 Re1 2.190(2) . ? 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(2) . . ? O2 C2 Re1 178.2(3) . . ? O3 C3 Re1 178.1(3) . . ? N1 C4 C10 106.1(2) . . ? N1 C4 C5 106.7(2) . . ? C10 C4 C5 107.55(19) . . ? N1 C4 H4 112.0 . . ? C10 C4 H4 112.0 . . ? C5 C4 H4 112.0 . . ? N3 C5 C6 121.9(2) . . ? N3 C5 C4 113.0(2) . . ? C6 C5 C4 125.1(2) . . ? C5 C6 C7 118.8(2) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 119.1(2) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C9 C8 C7 119.1(2) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? N3 C9 C8 121.9(2) . . ? N3 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? N2 C10 C11 121.9(2) . . ? N2 C10 C4 112.4(2) . . ? C11 C10 C4 125.8(2) . . ? C10 C11 C12 119.2(2) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 118.5(2) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? N2 C14 C13 121.7(2) . . ? N2 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? O4 C15 N1 124.2(2) . . ? O4 C15 C16 119.5(2) . . ? N1 C15 C16 116.3(2) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 N1 C4 117.3(2) . . ? C15 N1 Re1 138.62(18) . . ? C4 N1 Re1 103.80(14) . . ? C14 N2 C10 119.0(2) . . ? C14 N2 Re1 127.15(18) . . ? C10 N2 Re1 113.36(16) . . ? C9 N3 C5 119.1(2) . . ? C9 N3 Re1 127.82(18) . . ? C5 N3 Re1 113.08(16) . . ? C2 Re1 C3 90.04(13) . . ? C2 Re1 C1 90.57(12) . . ? C3 Re1 C1 87.72(11) . . ? C2 Re1 N1 97.46(10) . . ? C3 Re1 N1 100.12(10) . . ? C1 Re1 N1 168.73(10) . . ? C2 Re1 N3 96.51(11) . . ? C3 Re1 N3 172.05(9) . . ? C1 Re1 N3 96.68(9) . . ? N1 Re1 N3 74.62(8) . . ? C2 Re1 N2 172.26(10) . . ? C3 Re1 N2 91.76(10) . . ? C1 Re1 N2 97.02(10) . . ? N1 Re1 N2 74.81(8) . . ? N3 Re1 N2 81.15(8) . . ? 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 C4 C5 N3 38.4(3) . . . . ? C10 C4 C5 N3 -75.0(3) . . . . ? N1 C4 C5 C6 -143.6(2) . . . . ? C10 C4 C5 C6 102.9(3) . . . . ? N3 C5 C6 C7 -1.2(4) . . . . ? C4 C5 C6 C7 -179.0(2) . . . . ? C5 C6 C7 C8 1.3(4) . . . . ? C6 C7 C8 C9 -0.7(4) . . . . ? C7 C8 C9 N3 0.0(4) . . . . ? N1 C4 C10 N2 -43.3(3) . . . . ? C5 C4 C10 N2 70.6(3) . . . . ? N1 C4 C10 C11 136.0(2) . . . . ? C5 C4 C10 C11 -110.1(3) . . . . ? N2 C10 C11 C12 1.3(4) . . . . ? C4 C10 C11 C12 -178.0(2) . . . . ? C10 C11 C12 C13 -1.6(4) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C12 C13 C14 N2 0.8(4) . . . . ? O4 C15 N1 C4 -1.7(4) . . . . ? C16 C15 N1 C4 179.1(2) . . . . ? O4 C15 N1 Re1 -174.78(19) . . . . ? C16 C15 N1 Re1 6.0(4) . . . . ? C10 C4 N1 C15 -117.3(2) . . . . ? C5 C4 N1 C15 128.2(2) . . . . ? C10 C4 N1 Re1 57.96(19) . . . . ? C5 C4 N1 Re1 -56.52(19) . . . . ? C13 C14 N2 C10 -1.1(4) . . . . ? C13 C14 N2 Re1 170.45(18) . . . . ? C11 C10 N2 C14 0.1(4) . . . . ? C4 C10 N2 C14 179.4(2) . . . . ? C11 C10 N2 Re1 -172.60(18) . . . . ? C4 C10 N2 Re1 6.7(2) . . . . ? C8 C9 N3 C5 0.1(4) . . . . ? C8 C9 N3 Re1 179.36(18) . . . . ? C6 C5 N3 C9 0.6(4) . . . . ? C4 C5 N3 C9 178.6(2) . . . . ? C6 C5 N3 Re1 -178.84(18) . . . . ? C4 C5 N3 Re1 -0.8(2) . . . . ? O2 C2 Re1 C3 -64(9) . . . . ? O2 C2 Re1 C1 -151(9) . . . . ? O2 C2 Re1 N1 37(9) . . . . ? O2 C2 Re1 N3 112(9) . . . . ? O2 C2 Re1 N2 40(9) . . . . ? O3 C3 Re1 C2 -131(7) . . . . ? O3 C3 Re1 C1 -40(7) . . . . ? O3 C3 Re1 N1 131(7) . . . . ? O3 C3 Re1 N3 83(7) . . . . ? O3 C3 Re1 N2 57(7) . . . . ? O1 C1 Re1 C2 132(13) . . . . ? O1 C1 Re1 C3 42(13) . . . . ? O1 C1 Re1 N1 -92(13) . . . . ? O1 C1 Re1 N3 -131(13) . . . . ? O1 C1 Re1 N2 -49(13) . . . . ? C15 N1 Re1 C2 -48.6(3) . . . . ? C4 N1 Re1 C2 137.77(16) . . . . ? C15 N1 Re1 C3 42.8(3) . . . . ? C4 N1 Re1 C3 -130.85(16) . . . . ? C15 N1 Re1 C1 176.3(4) . . . . ? C4 N1 Re1 C1 2.7(5) . . . . ? C15 N1 Re1 N3 -143.3(3) . . . . ? C4 N1 Re1 N3 43.02(15) . . . . ? C15 N1 Re1 N2 131.9(3) . . . . ? C4 N1 Re1 N2 -41.78(15) . . . . ? C9 N3 Re1 C2 60.5(2) . . . . ? C5 N3 Re1 C2 -120.19(18) . . . . ? C9 N3 Re1 C3 -154.2(7) . . . . ? C5 N3 Re1 C3 25.2(7) . . . . ? C9 N3 Re1 C1 -30.9(2) . . . . ? C5 N3 Re1 C1 148.47(18) . . . . ? C9 N3 Re1 N1 156.5(2) . . . . ? C5 N3 Re1 N1 -24.21(16) . . . . ? C9 N3 Re1 N2 -127.0(2) . . . . ? C5 N3 Re1 N2 52.36(16) . . . . ? C14 N2 Re1 C2 -155.2(7) . . . . ? C10 N2 Re1 C2 16.8(8) . . . . ? C14 N2 Re1 C3 -51.8(2) . . . . ? C10 N2 Re1 C3 120.15(18) . . . . ? C14 N2 Re1 C1 36.1(2) . . . . ? C10 N2 Re1 C1 -151.93(17) . . . . ? C14 N2 Re1 N1 -151.8(2) . . . . ? C10 N2 Re1 N1 20.14(16) . . . . ? C14 N2 Re1 N3 131.8(2) . . . . ? C10 N2 Re1 N3 -56.22(16) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.817 _refine_diff_density_min -1.058 _refine_diff_density_rms 0.105 # Attachment '- 6b_CCDC821716.cif' data_pd-4-139 _database_code_depnum_ccdc_archive 'CCDC 821716' #TrackingRef '- 6b_CCDC821716.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H18 Br N4 O4 Re' _chemical_formula_weight 680.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.602(3) _cell_length_b 12.208(8) _cell_length_c 13.094(5) _cell_angle_alpha 74.81(4) _cell_angle_beta 80.92(4) _cell_angle_gamma 94.31(6) _cell_volume 1149.4(10) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.327 _cell_measurement_theta_max 12.318 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.966 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 7.062 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.1744 _exptl_absorpt_correction_T_max 0.4173 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 4336 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4005 _reflns_number_gt 3529 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 /PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 /PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'DIRDIF-99 (Beurskens, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0602P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4005 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C1 C 0.4520(8) 0.2317(5) 0.2572(5) 0.0288(13) Uani 1 1 d . . . C2 C 0.3468(9) 0.3933(5) 0.3444(5) 0.0329(13) Uani 1 1 d . . . C3 C 0.1914(9) 0.1784(5) 0.4241(5) 0.0366(14) Uani 1 1 d . . . C4 C 0.2857(7) 0.2599(4) 0.0421(4) 0.0225(11) Uani 1 1 d . . . H4 H 0.3857 0.2415 0.0826 0.027 Uiso 1 1 calc R . . C5 C 0.2610(6) 0.3836(4) 0.0342(4) 0.0202(10) Uani 1 1 d . . . C6 C 0.2529(7) 0.4633(5) -0.0619(4) 0.0283(12) Uani 1 1 d . . . H6 H 0.2643 0.4413 -0.1268 0.034 Uiso 1 1 calc R . . C7 C 0.2286(7) 0.5740(5) -0.0635(4) 0.0284(12) Uani 1 1 d . . . H7 H 0.2202 0.6289 -0.1285 0.034 Uiso 1 1 calc R . . C8 C 0.2168(7) 0.6037(4) 0.0324(4) 0.0281(12) Uani 1 1 d . . . H8 H 0.2044 0.6803 0.0336 0.034 Uiso 1 1 calc R . . C9 C 0.2230(7) 0.5224(4) 0.1243(4) 0.0247(11) Uani 1 1 d . . . H9 H 0.2130 0.5439 0.1894 0.030 Uiso 1 1 calc R . . C10 C 0.1191(7) 0.1805(4) 0.1081(4) 0.0211(11) Uani 1 1 d . . . C11 C 0.0084(7) 0.1174(4) 0.0630(4) 0.0259(12) Uani 1 1 d . . . H11 H 0.0313 0.1268 -0.0124 0.031 Uiso 1 1 calc R . . C12 C -0.1329(7) 0.0422(4) 0.1273(5) 0.0269(12) Uani 1 1 d . . . H12 H -0.2103 0.0002 0.0969 0.032 Uiso 1 1 calc R . . C13 C -0.1620(7) 0.0280(4) 0.2374(4) 0.0264(12) Uani 1 1 d . . . H13 H -0.2534 -0.0280 0.2844 0.032 Uiso 1 1 calc R . . C14 C -0.0556(7) 0.0967(4) 0.2771(4) 0.0257(11) Uani 1 1 d . . . H14 H -0.0800 0.0899 0.3521 0.031 Uiso 1 1 calc R . . C15 C 0.4838(7) 0.1849(4) -0.0816(4) 0.0234(11) Uani 1 1 d . . . C16 C 0.5357(5) 0.1772(3) -0.1941(2) 0.0223(11) Uani 1 1 d G . . C17 C 0.6200(5) 0.0842(3) -0.2101(2) 0.0312(13) Uani 1 1 d G . . H17 H 0.6428 0.0274 -0.1501 0.037 Uiso 1 1 calc R . . C18 C 0.6708(6) 0.0744(3) -0.3137(3) 0.0381(15) Uani 1 1 d G . . H18 H 0.7283 0.0109 -0.3246 0.046 Uiso 1 1 calc R . . C19 C 0.6374(6) 0.1575(3) -0.4014(2) 0.0429(16) Uani 1 1 d G . . H19 H 0.6721 0.1508 -0.4722 0.051 Uiso 1 1 calc R . . C20 C 0.5532(6) 0.2504(3) -0.3854(2) 0.0426(16) Uani 1 1 d G . . H20 H 0.5303 0.3073 -0.4453 0.051 Uiso 1 1 calc R . . C21 C 0.5023(5) 0.2603(2) -0.2817(3) 0.0330(13) Uani 1 1 d G . . H21 H 0.4448 0.3238 -0.2708 0.040 Uiso 1 1 calc R . . C22 C 0.0200(13) 0.3615(7) 0.6008(6) 0.061(2) Uani 1 1 d . . . H22A H 0.1365 0.3956 0.5554 0.091 Uiso 1 1 calc R . . H22B H -0.0607 0.4206 0.5993 0.091 Uiso 1 1 calc R . . H22C H -0.0321 0.3014 0.5735 0.091 Uiso 1 1 calc R . . C23 C 0.0439(8) 0.3126(5) 0.7102(5) 0.0345(13) Uani 1 1 d . . . N1 N 0.3403(6) 0.2418(4) -0.0618(4) 0.0248(10) Uani 1 1 d . . . N2 N 0.0829(6) 0.1740(3) 0.2142(3) 0.0200(9) Uani 1 1 d . . . N3 N 0.2425(6) 0.4131(3) 0.1282(3) 0.0222(9) Uani 1 1 d . . . N4 N 0.0620(8) 0.2774(5) 0.7955(4) 0.0468(14) Uani 1 1 d . . . O1 O 0.5825(6) 0.1934(4) 0.2448(4) 0.0447(11) Uani 1 1 d . . . O2 O 0.4209(7) 0.4571(4) 0.3799(4) 0.0491(12) Uani 1 1 d . . . O3 O 0.1727(7) 0.1124(4) 0.5075(3) 0.0526(13) Uani 1 1 d . . . O4 O 0.5676(5) 0.1437(3) -0.0112(3) 0.0313(9) Uani 1 1 d . . . Re1 Re 0.22795(3) 0.287515(16) 0.286710(15) 0.02120(9) Uani 1 1 d . . . Br1 Br -0.08431(8) 0.35737(5) 0.33460(4) 0.03028(14) Uani 1 1 d . . . H1 H 0.276(8) 0.258(5) -0.107(5) 0.024(16) Uiso 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 0.035(3) 0.023(3) 0.031(3) -0.006(2) -0.018(3) 0.003(2) C2 0.052(4) 0.024(3) 0.022(3) -0.001(2) -0.014(3) 0.005(3) C3 0.051(4) 0.031(3) 0.033(4) -0.016(3) -0.012(3) -0.002(3) C4 0.025(3) 0.028(3) 0.014(2) -0.007(2) -0.003(2) 0.003(2) C5 0.020(3) 0.022(3) 0.015(2) -0.002(2) 0.001(2) -0.001(2) C6 0.033(3) 0.030(3) 0.020(3) -0.004(2) -0.006(2) 0.002(2) C7 0.035(3) 0.024(3) 0.020(3) 0.005(2) -0.004(2) 0.001(2) C8 0.028(3) 0.019(3) 0.030(3) 0.002(2) -0.003(2) -0.001(2) C9 0.032(3) 0.021(3) 0.022(3) -0.007(2) -0.007(2) 0.001(2) C10 0.029(3) 0.018(2) 0.016(2) -0.004(2) -0.003(2) 0.007(2) C11 0.035(3) 0.023(3) 0.023(3) -0.010(2) -0.010(2) 0.004(2) C12 0.029(3) 0.023(3) 0.035(3) -0.016(2) -0.009(2) 0.004(2) C13 0.030(3) 0.019(2) 0.027(3) -0.004(2) -0.001(2) 0.001(2) C14 0.037(3) 0.021(3) 0.017(3) -0.002(2) -0.002(2) 0.003(2) C15 0.033(3) 0.012(2) 0.022(3) -0.003(2) -0.003(2) -0.004(2) C16 0.029(3) 0.015(2) 0.019(3) -0.003(2) 0.002(2) -0.001(2) C17 0.042(3) 0.024(3) 0.027(3) -0.006(2) -0.006(3) 0.009(2) C18 0.047(4) 0.028(3) 0.037(3) -0.014(3) 0.008(3) 0.004(3) C19 0.050(4) 0.051(4) 0.022(3) -0.009(3) 0.010(3) 0.005(3) C20 0.058(4) 0.041(4) 0.018(3) 0.003(3) 0.011(3) 0.015(3) C21 0.044(3) 0.024(3) 0.022(3) 0.005(2) 0.002(3) 0.007(2) C22 0.105(7) 0.056(5) 0.029(4) -0.015(3) -0.028(4) 0.015(4) C23 0.042(4) 0.039(3) 0.024(3) -0.010(3) -0.009(3) 0.009(3) N1 0.029(2) 0.032(3) 0.015(2) -0.0077(19) -0.0061(19) 0.0083(19) N2 0.028(2) 0.017(2) 0.013(2) -0.0029(16) 0.0005(17) 0.0033(17) N3 0.030(2) 0.017(2) 0.016(2) 0.0014(17) -0.0052(18) 0.0020(17) N4 0.058(4) 0.056(4) 0.025(3) -0.006(3) -0.011(3) 0.014(3) O1 0.039(3) 0.032(2) 0.064(3) -0.009(2) -0.017(2) 0.008(2) O2 0.080(4) 0.026(2) 0.047(3) -0.011(2) -0.031(3) 0.000(2) O3 0.090(4) 0.040(3) 0.016(2) 0.011(2) -0.017(2) -0.010(2) O4 0.041(2) 0.031(2) 0.026(2) -0.0103(17) -0.0122(18) 0.0112(18) Re1 0.03359(14) 0.01653(12) 0.01267(13) -0.00150(8) -0.00701(8) 0.00142(8) Br1 0.0407(3) 0.0326(3) 0.0180(3) -0.0092(2) -0.0024(2) 0.0061(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.135(7) . ? C1 Re1 1.902(6) . ? C2 O2 1.161(7) . ? C2 Re1 1.898(6) . ? C3 O3 1.156(7) . ? C3 Re1 1.902(6) . ? C4 N1 1.437(7) . ? C4 C5 1.514(7) . ? C4 C10 1.524(7) . ? C4 H4 1.0000 . ? C5 N3 1.360(7) . ? C5 C6 1.389(7) . ? C6 C7 1.373(8) . ? C6 H6 0.9500 . ? C7 C8 1.386(8) . ? C7 H7 0.9500 . ? C8 C9 1.355(7) . ? C8 H8 0.9500 . ? C9 N3 1.342(7) . ? C9 H9 0.9500 . ? C10 N2 1.353(6) . ? C10 C11 1.396(7) . ? C11 C12 1.367(8) . ? C11 H11 0.9500 . ? C12 C13 1.386(8) . ? C12 H12 0.9500 . ? C13 C14 1.373(8) . ? C13 H13 0.9500 . ? C14 N2 1.359(7) . ? C14 H14 0.9500 . ? C15 O4 1.224(6) . ? C15 N1 1.363(7) . ? C15 C16 1.494(6) . ? C16 C17 1.3900 . ? C16 C21 1.3900 . ? C17 C18 1.3900 . ? C17 H17 0.9500 . ? C18 C19 1.3900 . ? C18 H18 0.9500 . ? C19 C20 1.3900 . ? C19 H19 0.9500 . ? C20 C21 1.3900 . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.446(9) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N4 1.121(8) . ? N1 H1 0.82(6) . ? N2 Re1 2.198(4) . ? N3 Re1 2.215(4) . ? Re1 Br1 2.6212(14) . ? 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 176.0(5) . . ? O2 C2 Re1 179.2(5) . . ? O3 C3 Re1 178.7(6) . . ? N1 C4 C5 112.1(4) . . ? N1 C4 C10 112.9(4) . . ? C5 C4 C10 110.9(4) . . ? N1 C4 H4 106.8 . . ? C5 C4 H4 106.8 . . ? C10 C4 H4 106.8 . . ? N3 C5 C6 120.8(5) . . ? N3 C5 C4 116.2(4) . . ? C6 C5 C4 123.1(5) . . ? C7 C6 C5 120.2(5) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 118.3(5) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? C9 C8 C7 119.3(5) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? N3 C9 C8 123.5(5) . . ? N3 C9 H9 118.2 . . ? C8 C9 H9 118.2 . . ? N2 C10 C11 121.1(5) . . ? N2 C10 C4 116.3(4) . . ? C11 C10 C4 122.6(5) . . ? C12 C11 C10 120.0(5) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 119.2(5) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 118.5(5) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? N2 C14 C13 123.1(5) . . ? N2 C14 H14 118.4 . . ? C13 C14 H14 118.4 . . ? O4 C15 N1 121.8(5) . . ? O4 C15 C16 121.6(5) . . ? N1 C15 C16 116.6(4) . . ? C17 C16 C21 120.0 . . ? C17 C16 C15 118.4(3) . . ? C21 C16 C15 121.6(3) . . ? C16 C17 C18 120.0 . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.0 . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C21 C20 C19 120.0 . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C16 120.0 . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N4 C23 C22 178.2(7) . . ? C15 N1 C4 121.0(5) . . ? C15 N1 H1 119(4) . . ? C4 N1 H1 119(4) . . ? C10 N2 C14 117.8(4) . . ? C10 N2 Re1 123.1(3) . . ? C14 N2 Re1 119.0(3) . . ? C9 N3 C5 117.9(4) . . ? C9 N3 Re1 119.0(4) . . ? C5 N3 Re1 122.9(3) . . ? C2 Re1 C3 88.9(2) . . ? C2 Re1 C1 87.9(3) . . ? C3 Re1 C1 86.7(3) . . ? C2 Re1 N2 176.43(18) . . ? C3 Re1 N2 93.9(2) . . ? C1 Re1 N2 94.4(2) . . ? C2 Re1 N3 93.9(2) . . ? C3 Re1 N3 174.6(2) . . ? C1 Re1 N3 98.1(2) . . ? N2 Re1 N3 83.17(16) . . ? C2 Re1 Br1 92.4(2) . . ? C3 Re1 Br1 91.0(2) . . ? C1 Re1 Br1 177.66(17) . . ? N2 Re1 Br1 85.31(12) . . ? N3 Re1 Br1 84.21(13) . . ? 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 C4 C5 N3 -168.1(4) . . . . ? C10 C4 C5 N3 64.6(6) . . . . ? N1 C4 C5 C6 13.4(7) . . . . ? C10 C4 C5 C6 -113.9(5) . . . . ? N3 C5 C6 C7 0.9(8) . . . . ? C4 C5 C6 C7 179.4(5) . . . . ? C5 C6 C7 C8 1.4(8) . . . . ? C6 C7 C8 C9 -2.3(8) . . . . ? C7 C8 C9 N3 0.9(8) . . . . ? N1 C4 C10 N2 165.6(4) . . . . ? C5 C4 C10 N2 -67.6(6) . . . . ? N1 C4 C10 C11 -14.4(7) . . . . ? C5 C4 C10 C11 112.4(5) . . . . ? N2 C10 C11 C12 -4.1(8) . . . . ? C4 C10 C11 C12 175.9(5) . . . . ? C10 C11 C12 C13 -1.4(8) . . . . ? C11 C12 C13 C14 5.0(8) . . . . ? C12 C13 C14 N2 -3.5(8) . . . . ? O4 C15 C16 C17 29.0(6) . . . . ? N1 C15 C16 C17 -152.0(4) . . . . ? O4 C15 C16 C21 -150.7(4) . . . . ? N1 C15 C16 C21 28.2(6) . . . . ? C21 C16 C17 C18 0.0 . . . . ? C15 C16 C17 C18 -179.8(4) . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C20 0.0 . . . . ? C18 C19 C20 C21 0.0 . . . . ? C19 C20 C21 C16 0.0 . . . . ? C17 C16 C21 C20 0.0 . . . . ? C15 C16 C21 C20 179.8(4) . . . . ? O4 C15 N1 C4 2.6(8) . . . . ? C16 C15 N1 C4 -176.3(4) . . . . ? C5 C4 N1 C15 130.0(5) . . . . ? C10 C4 N1 C15 -103.9(5) . . . . ? C11 C10 N2 C14 5.5(7) . . . . ? C4 C10 N2 C14 -174.5(4) . . . . ? C11 C10 N2 Re1 -171.3(4) . . . . ? C4 C10 N2 Re1 8.7(6) . . . . ? C13 C14 N2 C10 -1.8(8) . . . . ? C13 C14 N2 Re1 175.2(4) . . . . ? C8 C9 N3 C5 1.5(8) . . . . ? C8 C9 N3 Re1 -175.1(4) . . . . ? C6 C5 N3 C9 -2.4(7) . . . . ? C4 C5 N3 C9 179.0(4) . . . . ? C6 C5 N3 Re1 174.0(4) . . . . ? C4 C5 N3 Re1 -4.5(6) . . . . ? O2 C2 Re1 C3 61(42) . . . . ? O2 C2 Re1 C1 -25(42) . . . . ? O2 C2 Re1 N2 -157(40) . . . . ? O2 C2 Re1 N3 -123(42) . . . . ? O2 C2 Re1 Br1 152(42) . . . . ? O3 C3 Re1 C2 -52(24) . . . . ? O3 C3 Re1 C1 36(24) . . . . ? O3 C3 Re1 N2 130(24) . . . . ? O3 C3 Re1 N3 -173(100) . . . . ? O3 C3 Re1 Br1 -145(24) . . . . ? O1 C1 Re1 C2 99(7) . . . . ? O1 C1 Re1 C3 10(7) . . . . ? O1 C1 Re1 N2 -84(7) . . . . ? O1 C1 Re1 N3 -167(7) . . . . ? O1 C1 Re1 Br1 0(11) . . . . ? C10 N2 Re1 C2 67(3) . . . . ? C14 N2 Re1 C2 -110(3) . . . . ? C10 N2 Re1 C3 -151.8(4) . . . . ? C14 N2 Re1 C3 31.4(4) . . . . ? C10 N2 Re1 C1 -64.8(4) . . . . ? C14 N2 Re1 C1 118.4(4) . . . . ? C10 N2 Re1 N3 32.8(4) . . . . ? C14 N2 Re1 N3 -144.0(4) . . . . ? C10 N2 Re1 Br1 117.5(4) . . . . ? C14 N2 Re1 Br1 -59.3(4) . . . . ? C9 N3 Re1 C2 -36.8(4) . . . . ? C5 N3 Re1 C2 146.8(4) . . . . ? C9 N3 Re1 C3 83(2) . . . . ? C5 N3 Re1 C3 -93(2) . . . . ? C9 N3 Re1 C1 -125.3(4) . . . . ? C5 N3 Re1 C1 58.3(4) . . . . ? C9 N3 Re1 N2 141.2(4) . . . . ? C5 N3 Re1 N2 -35.2(4) . . . . ? C9 N3 Re1 Br1 55.2(4) . . . . ? C5 N3 Re1 Br1 -121.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N4 0.82(6) 2.21(6) 3.019(7) 168(6) 1_554 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.829 _refine_diff_density_min -2.056 _refine_diff_density_rms 0.153 # Attachment '- 8b.HBr_CCDC821717.cif' data_pd-9-77 _database_code_depnum_ccdc_archive 'CCDC 821717' #TrackingRef '- 8b.HBr_CCDC821717.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H19 Br N3 O4 Re' _chemical_formula_weight 715.56 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a b' _symmetry_space_group_name_Hall '-P 2bc 2ac' _symmetry_Int_Tables_number 61 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' '-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 17.395(2) _cell_length_b 13.956(2) _cell_length_c 20.464(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4967.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 94163 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.913 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2752 _exptl_absorpt_coefficient_mu 6.540 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4209 _exptl_absorpt_correction_T_max 0.8280 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 25325 _diffrn_reflns_av_R_equivalents 0.0897 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4955 _reflns_number_gt 3630 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'DIRDIF08 (Beurskens et al, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+218.7775P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4955 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1182 _refine_ls_R_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.2033 _refine_ls_wR_factor_gt 0.1816 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 0.1398(10) 0.1740(14) 0.0033(7) 0.039(4) Uani 1 1 d . . . C2 C 0.1678(9) 0.2350(12) 0.1229(7) 0.031(3) Uani 1 1 d . . . C3 C 0.2590(9) 0.2835(13) 0.0197(6) 0.032(4) Uani 1 1 d . . . C4 C 0.3417(8) 0.0245(11) 0.1050(6) 0.026(3) Uani 1 1 d . . . C5 C 0.2630(8) -0.0205(10) 0.1249(6) 0.022(3) Uani 1 1 d . . . C6 C 0.2550(10) -0.1063(12) 0.1583(7) 0.036(4) Uani 1 1 d . . . H6 H 0.2982 -0.1397 0.1753 0.043 Uiso 1 1 calc R . . C7 C 0.1792(10) -0.1418(12) 0.1660(8) 0.040(4) Uani 1 1 d . . . H7 H 0.1708 -0.2014 0.1873 0.048 Uiso 1 1 calc R . . C8 C 0.1183(11) -0.0906(15) 0.1428(8) 0.044(4) Uani 1 1 d . . . H8 H 0.0674 -0.1141 0.1481 0.053 Uiso 1 1 calc R . . C9 C 0.1307(8) -0.0059(11) 0.1123(6) 0.025(2) Uani 1 1 d . . . H9 H 0.0881 0.0302 0.0969 0.030 Uiso 1 1 calc R . . C10 C 0.3464(8) 0.0184(13) 0.0299(7) 0.032(4) Uani 1 1 d . . . C11 C 0.4020(8) -0.0416(11) -0.0048(7) 0.027(3) Uani 1 1 d . . . H11 H 0.4395 -0.0780 0.0180 0.033 Uiso 1 1 calc R . . C12 C 0.3975(9) -0.0431(14) -0.0721(7) 0.037(4) Uani 1 1 d . . . H12 H 0.4327 -0.0800 -0.0971 0.044 Uiso 1 1 calc R . . C13 C 0.3407(9) 0.0103(15) -0.1028(7) 0.041(4) Uani 1 1 d . . . H13 H 0.3358 0.0077 -0.1490 0.049 Uiso 1 1 calc R . . C14 C 0.2888(8) 0.0697(11) -0.0654(6) 0.025(2) Uani 1 1 d . . . H14 H 0.2504 0.1070 -0.0864 0.030 Uiso 1 1 calc R . . C15 C 0.3953(9) 0.1872(13) 0.0965(6) 0.033(4) Uani 1 1 d . . . C16 C 0.3954(6) 0.2898(5) 0.1141(5) 0.031(3) Uani 1 1 d G . . C17 C 0.3509(5) 0.3262(7) 0.1647(4) 0.033(3) Uani 1 1 d G . . H17 H 0.3226 0.2839 0.1920 0.039 Uiso 1 1 calc R . . C18 C 0.3477(5) 0.4244(7) 0.1754(4) 0.039(4) Uani 1 1 d G . . H18 H 0.3173 0.4493 0.2101 0.047 Uiso 1 1 calc R . . C19 C 0.3890(6) 0.4863(5) 0.1355(5) 0.038(4) Uani 1 1 d G . . H19 H 0.3869 0.5535 0.1428 0.046 Uiso 1 1 calc R . . C20 C 0.4335(5) 0.4500(6) 0.0848(4) 0.034(4) Uani 1 1 d G . . H20 H 0.4618 0.4923 0.0575 0.040 Uiso 1 1 calc R . . C21 C 0.4367(5) 0.3517(7) 0.0741(4) 0.028(3) Uani 1 1 d G . . H21 H 0.4671 0.3268 0.0394 0.034 Uiso 1 1 calc R . . C22 C 0.4076(5) -0.0229(7) 0.1443(4) 0.030(3) Uani 1 1 d G . . C23 C 0.4496(6) 0.0301(6) 0.1893(5) 0.035(4) Uani 1 1 d G . . H23 H 0.4378 0.0958 0.1964 0.042 Uiso 1 1 calc R . . C24 C 0.5090(5) -0.0129(9) 0.2241(4) 0.047(5) Uani 1 1 d G . . H24 H 0.5377 0.0234 0.2549 0.057 Uiso 1 1 calc R . . C25 C 0.5263(5) -0.1089(9) 0.2138(5) 0.047(5) Uani 1 1 d G . . H25 H 0.5669 -0.1383 0.2375 0.057 Uiso 1 1 calc R . . C26 C 0.4843(6) -0.1619(7) 0.1687(5) 0.048(5) Uani 1 1 d G . . H26 H 0.4962 -0.2276 0.1617 0.057 Uiso 1 1 calc R . . C27 C 0.4250(6) -0.1189(7) 0.1339(5) 0.039(4) Uani 1 1 d G . . H27 H 0.3963 -0.1552 0.1031 0.047 Uiso 1 1 calc R . . Br1 Br 0.23832(10) 0.13976(13) -0.23647(7) 0.0393(4) Uani 1 1 d . . . N1 N 0.3329(7) 0.1266(9) 0.1182(5) 0.028(3) Uani 1 1 d . . . N2 N 0.2959(7) 0.0709(11) -0.0020(6) 0.034(3) Uani 1 1 d . . . N3 N 0.2020(7) 0.0275(10) 0.1035(5) 0.030(3) Uani 1 1 d . . . O1 O 0.0866(6) 0.1785(9) -0.0326(5) 0.040(3) Uani 1 1 d . . . O2 O 0.1326(7) 0.2759(9) 0.1616(5) 0.042(3) Uani 1 1 d . . . O4 O 0.4452(5) 0.1523(8) 0.0615(4) 0.029(2) Uani 1 1 d . . . O3 O 0.2763(6) 0.3569(9) -0.0040(5) 0.040(3) Uani 1 1 d . . . Re1 Re 0.22654(3) 0.16466(5) 0.05856(3) 0.0274(2) Uani 1 1 d . . . H1 H 0.310(9) 0.138(12) -0.232(7) 0.033 Uiso 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 0.041(9) 0.047(11) 0.030(8) -0.013(8) 0.009(7) -0.003(8) C2 0.036(8) 0.038(9) 0.020(6) -0.001(7) -0.009(6) -0.011(7) C3 0.040(9) 0.045(11) 0.012(6) -0.004(6) -0.004(6) 0.019(8) C4 0.023(7) 0.031(9) 0.024(7) -0.005(6) -0.003(5) 0.010(6) C5 0.037(8) 0.015(7) 0.014(6) -0.009(5) -0.004(5) -0.004(6) C6 0.047(9) 0.032(9) 0.027(8) -0.013(7) -0.004(6) -0.005(7) C7 0.052(10) 0.026(9) 0.041(9) 0.011(7) 0.010(7) -0.002(8) C8 0.047(10) 0.050(12) 0.035(9) 0.003(8) 0.001(7) 0.003(9) C9 0.027(5) 0.028(6) 0.021(5) -0.003(4) -0.006(4) -0.013(4) C10 0.021(7) 0.052(11) 0.022(7) -0.001(7) -0.009(5) 0.004(7) C11 0.033(8) 0.025(8) 0.025(7) -0.009(6) -0.004(6) 0.010(6) C12 0.035(8) 0.053(12) 0.023(7) -0.006(7) 0.001(6) -0.003(8) C13 0.038(9) 0.066(13) 0.020(7) -0.001(8) 0.001(6) 0.002(9) C14 0.027(5) 0.028(6) 0.021(5) -0.003(4) -0.006(4) -0.013(4) C15 0.033(8) 0.051(11) 0.014(6) 0.005(6) 0.003(5) -0.018(8) C16 0.026(7) 0.034(9) 0.031(8) -0.003(7) 0.000(6) 0.001(7) C17 0.041(8) 0.033(9) 0.024(7) -0.002(7) 0.002(6) 0.005(7) C18 0.042(9) 0.051(12) 0.024(7) 0.008(8) -0.005(6) 0.010(8) C19 0.021(7) 0.051(12) 0.043(9) 0.007(8) -0.001(6) 0.001(7) C20 0.032(8) 0.033(10) 0.035(8) -0.002(7) -0.011(6) -0.006(7) C21 0.029(7) 0.028(9) 0.029(7) -0.012(6) 0.006(6) -0.002(6) C22 0.036(8) 0.026(9) 0.027(7) -0.002(6) 0.003(6) -0.005(7) C23 0.023(7) 0.059(12) 0.023(7) -0.002(7) -0.007(5) 0.003(7) C24 0.035(9) 0.085(17) 0.022(7) 0.004(9) 0.000(6) -0.004(10) C25 0.041(10) 0.075(16) 0.026(8) 0.011(9) -0.009(7) 0.006(10) C26 0.048(10) 0.051(12) 0.044(10) 0.010(9) 0.011(8) 0.020(9) C27 0.038(9) 0.041(11) 0.039(9) -0.001(8) 0.002(7) 0.001(8) Br1 0.0492(10) 0.0459(11) 0.0227(7) 0.0045(7) -0.0093(6) -0.0057(8) N1 0.033(7) 0.029(7) 0.021(6) 0.006(5) -0.010(5) 0.012(6) N2 0.030(7) 0.050(10) 0.021(6) -0.003(6) -0.004(5) -0.004(6) N3 0.029(6) 0.042(9) 0.019(5) -0.011(6) 0.001(5) 0.004(6) O1 0.032(6) 0.056(9) 0.034(6) 0.004(6) -0.004(5) -0.001(6) O2 0.064(8) 0.033(7) 0.030(6) 0.002(5) 0.010(5) 0.013(6) O4 0.027(5) 0.034(7) 0.025(5) 0.007(5) 0.004(4) 0.009(4) O3 0.039(6) 0.046(8) 0.036(6) 0.005(6) -0.003(5) -0.004(6) Re1 0.0269(3) 0.0362(4) 0.0191(3) 0.0018(2) 0.0013(2) 0.0031(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.182(19) . ? C1 Re1 1.890(17) . ? C2 O2 1.152(19) . ? C2 Re1 1.934(16) . ? C3 O3 1.17(2) . ? C3 Re1 1.924(18) . ? C4 N1 1.459(19) . ? C4 C10 1.542(19) . ? C4 C22 1.548(15) . ? C4 C5 1.560(19) . ? C5 N3 1.330(18) . ? C5 C6 1.39(2) . ? C6 C7 1.42(2) . ? C6 H6 0.9500 . ? C7 C8 1.36(2) . ? C7 H7 0.9500 . ? C8 C9 1.35(2) . ? C8 H8 0.9500 . ? C9 N3 1.336(18) . ? C9 H9 0.9500 . ? C10 N2 1.318(19) . ? C10 C11 1.46(2) . ? C11 C12 1.379(19) . ? C11 H11 0.9500 . ? C12 C13 1.39(2) . ? C12 H12 0.9500 . ? C13 C14 1.45(2) . ? C13 H13 0.9500 . ? C14 N2 1.302(17) . ? C14 H14 0.9500 . ? C15 O4 1.225(18) . ? C15 N1 1.446(19) . ? C15 C16 1.477(19) . ? C16 C17 1.3900 . ? C16 C21 1.3900 . ? C17 C18 1.3900 . ? C17 H17 0.9500 . ? C18 C19 1.3900 . ? C18 H18 0.9500 . ? C19 C20 1.3900 . ? C19 H19 0.9500 . ? C20 C21 1.3900 . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.3900 . ? C22 C27 1.3900 . ? C23 C24 1.3900 . ? C23 H23 0.9500 . ? C24 C25 1.3900 . ? C24 H24 0.9500 . ? C25 C26 1.3900 . ? C25 H25 0.9500 . ? C26 C27 1.3900 . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? Br1 H1 1.25(16) . ? N1 Re1 2.280(11) . ? N2 Re1 2.169(13) . ? N3 Re1 2.166(14) . ? 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 178.3(14) . . ? O2 C2 Re1 179.1(15) . . ? O3 C3 Re1 177.7(13) . . ? N1 C4 C10 104.1(12) . . ? N1 C4 C22 113.5(11) . . ? C10 C4 C22 117.0(11) . . ? N1 C4 C5 104.7(11) . . ? C10 C4 C5 106.6(11) . . ? C22 C4 C5 110.1(11) . . ? N3 C5 C6 121.2(14) . . ? N3 C5 C4 114.3(12) . . ? C6 C5 C4 124.4(13) . . ? C5 C6 C7 116.7(15) . . ? C5 C6 H6 121.6 . . ? C7 C6 H6 121.6 . . ? C8 C7 C6 120.1(16) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 119.6(17) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? N3 C9 C8 121.0(15) . . ? N3 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? N2 C10 C11 121.2(13) . . ? N2 C10 C4 115.3(13) . . ? C11 C10 C4 123.5(12) . . ? C12 C11 C10 117.1(14) . . ? C12 C11 H11 121.4 . . ? C10 C11 H11 121.4 . . ? C11 C12 C13 118.9(15) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C14 120.9(14) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? N2 C14 C13 118.4(14) . . ? N2 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? O4 C15 N1 118.6(15) . . ? O4 C15 C16 121.8(13) . . ? N1 C15 C16 119.5(12) . . ? C17 C16 C21 120.0 . . ? C17 C16 C15 122.4(8) . . ? C21 C16 C15 117.4(8) . . ? C18 C17 C16 120.0 . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.0 . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 120.0 . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.0 . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C16 120.0 . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? C23 C22 C27 120.0 . . ? C23 C22 C4 120.4(8) . . ? C27 C22 C4 119.6(8) . . ? C24 C23 C22 120.0 . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 120.0 . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.0 . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 120.0 . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C22 120.0 . . ? C26 C27 H27 120.0 . . ? C22 C27 H27 120.0 . . ? C15 N1 C4 115.8(12) . . ? C15 N1 Re1 107.9(9) . . ? C4 N1 Re1 102.3(8) . . ? C14 N2 C10 123.3(14) . . ? C14 N2 Re1 121.6(11) . . ? C10 N2 Re1 115.1(10) . . ? C5 N3 C9 121.3(14) . . ? C5 N3 Re1 115.3(10) . . ? C9 N3 Re1 123.3(11) . . ? C1 Re1 C3 85.9(7) . . ? C1 Re1 C2 87.2(6) . . ? C3 Re1 C2 89.9(6) . . ? C1 Re1 N3 99.0(6) . . ? C3 Re1 N3 174.3(5) . . ? C2 Re1 N3 93.2(6) . . ? C1 Re1 N2 98.3(6) . . ? C3 Re1 N2 96.9(6) . . ? C2 Re1 N2 171.5(6) . . ? N3 Re1 N2 79.6(5) . . ? C1 Re1 N1 169.9(6) . . ? C3 Re1 N1 100.6(5) . . ? C2 Re1 N1 100.5(5) . . ? N3 Re1 N1 74.2(5) . . ? N2 Re1 N1 73.4(4) . . ? 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 C4 C5 N3 45.4(14) . . . . ? C10 C4 C5 N3 -64.5(15) . . . . ? C22 C4 C5 N3 167.7(11) . . . . ? N1 C4 C5 C6 -138.7(13) . . . . ? C10 C4 C5 C6 111.4(14) . . . . ? C22 C4 C5 C6 -16.4(17) . . . . ? N3 C5 C6 C7 3(2) . . . . ? C4 C5 C6 C7 -173.1(13) . . . . ? C5 C6 C7 C8 -2(2) . . . . ? C6 C7 C8 C9 0(3) . . . . ? C7 C8 C9 N3 1(2) . . . . ? N1 C4 C10 N2 -44.4(17) . . . . ? C22 C4 C10 N2 -170.5(13) . . . . ? C5 C4 C10 N2 65.9(18) . . . . ? N1 C4 C10 C11 136.2(15) . . . . ? C22 C4 C10 C11 10(2) . . . . ? C5 C4 C10 C11 -113.5(16) . . . . ? N2 C10 C11 C12 -2(2) . . . . ? C4 C10 C11 C12 177.3(15) . . . . ? C10 C11 C12 C13 -1(2) . . . . ? C11 C12 C13 C14 3(3) . . . . ? C12 C13 C14 N2 -1(2) . . . . ? O4 C15 C16 C17 -164.8(10) . . . . ? N1 C15 C16 C17 18.2(16) . . . . ? O4 C15 C16 C21 20.9(17) . . . . ? N1 C15 C16 C21 -156.1(9) . . . . ? C21 C16 C17 C18 0.0 . . . . ? C15 C16 C17 C18 -174.2(11) . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C20 0.0 . . . . ? C18 C19 C20 C21 0.0 . . . . ? C19 C20 C21 C16 0.0 . . . . ? C17 C16 C21 C20 0.0 . . . . ? C15 C16 C21 C20 174.5(10) . . . . ? N1 C4 C22 C23 3.0(14) . . . . ? C10 C4 C22 C23 124.3(12) . . . . ? C5 C4 C22 C23 -113.9(10) . . . . ? N1 C4 C22 C27 -176.7(9) . . . . ? C10 C4 C22 C27 -55.4(15) . . . . ? C5 C4 C22 C27 66.4(12) . . . . ? C27 C22 C23 C24 0.0 . . . . ? C4 C22 C23 C24 -179.7(10) . . . . ? C22 C23 C24 C25 0.0 . . . . ? C23 C24 C25 C26 0.0 . . . . ? C24 C25 C26 C27 0.0 . . . . ? C25 C26 C27 C22 0.0 . . . . ? C23 C22 C27 C26 0.0 . . . . ? C4 C22 C27 C26 179.7(10) . . . . ? O4 C15 N1 C4 9.6(18) . . . . ? C16 C15 N1 C4 -173.4(11) . . . . ? O4 C15 N1 Re1 -104.4(13) . . . . ? C16 C15 N1 Re1 72.7(12) . . . . ? C10 C4 N1 C15 -61.1(14) . . . . ? C22 C4 N1 C15 67.2(14) . . . . ? C5 C4 N1 C15 -172.8(10) . . . . ? C10 C4 N1 Re1 56.0(10) . . . . ? C22 C4 N1 Re1 -175.7(8) . . . . ? C5 C4 N1 Re1 -55.7(10) . . . . ? C13 C14 N2 C10 -2(2) . . . . ? C13 C14 N2 Re1 175.8(11) . . . . ? C11 C10 N2 C14 4(3) . . . . ? C4 C10 N2 C14 -175.6(14) . . . . ? C11 C10 N2 Re1 -174.3(12) . . . . ? C4 C10 N2 Re1 6.2(18) . . . . ? C6 C5 N3 C9 -1.3(19) . . . . ? C4 C5 N3 C9 174.8(12) . . . . ? C6 C5 N3 Re1 175.9(10) . . . . ? C4 C5 N3 Re1 -8.0(13) . . . . ? C8 C9 N3 C5 -1(2) . . . . ? C8 C9 N3 Re1 -177.5(11) . . . . ? O1 C1 Re1 C3 88(58) . . . . ? O1 C1 Re1 C2 178(100) . . . . ? O1 C1 Re1 N3 -89(58) . . . . ? O1 C1 Re1 N2 -8(58) . . . . ? O1 C1 Re1 N1 -42(60) . . . . ? O3 C3 Re1 C1 36(31) . . . . ? O3 C3 Re1 C2 -51(31) . . . . ? O3 C3 Re1 N3 -174(100) . . . . ? O3 C3 Re1 N2 134(31) . . . . ? O3 C3 Re1 N1 -152(31) . . . . ? O2 C2 Re1 C1 97(88) . . . . ? O2 C2 Re1 C3 -178(100) . . . . ? O2 C2 Re1 N3 -2(88) . . . . ? O2 C2 Re1 N2 -34(90) . . . . ? O2 C2 Re1 N1 -77(88) . . . . ? C5 N3 Re1 C1 153.9(10) . . . . ? C9 N3 Re1 C1 -29.0(12) . . . . ? C5 N3 Re1 C3 4(5) . . . . ? C9 N3 Re1 C3 -179(100) . . . . ? C5 N3 Re1 C2 -118.4(10) . . . . ? C9 N3 Re1 C2 58.6(11) . . . . ? C5 N3 Re1 N2 57.1(9) . . . . ? C9 N3 Re1 N2 -125.8(11) . . . . ? C5 N3 Re1 N1 -18.4(9) . . . . ? C9 N3 Re1 N1 158.7(11) . . . . ? C14 N2 Re1 C1 27.8(13) . . . . ? C10 N2 Re1 C1 -154.0(13) . . . . ? C14 N2 Re1 C3 -59.1(13) . . . . ? C10 N2 Re1 C3 119.1(12) . . . . ? C14 N2 Re1 C2 158(3) . . . . ? C10 N2 Re1 C2 -24(4) . . . . ? C14 N2 Re1 N3 125.5(12) . . . . ? C10 N2 Re1 N3 -56.3(12) . . . . ? C14 N2 Re1 N1 -158.1(13) . . . . ? C10 N2 Re1 N1 20.1(11) . . . . ? C15 N1 Re1 C1 115(3) . . . . ? C4 N1 Re1 C1 -7(4) . . . . ? C15 N1 Re1 C3 -13.8(11) . . . . ? C4 N1 Re1 C3 -136.5(9) . . . . ? C15 N1 Re1 C2 -105.7(10) . . . . ? C4 N1 Re1 C2 131.7(9) . . . . ? C15 N1 Re1 N3 164.0(10) . . . . ? C4 N1 Re1 N3 41.3(8) . . . . ? C15 N1 Re1 N2 80.3(10) . . . . ? C4 N1 Re1 N2 -42.3(8) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 3.136 _refine_diff_density_min -2.048 _refine_diff_density_rms 0.312 # Attachment '- 7c_CCDC821718.cif' data_pd-9-80 _database_code_depnum_ccdc_archive 'CCDC 821718' #TrackingRef '- 7c_CCDC821718.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Br N3 O4 Re' _chemical_formula_weight 653.50 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 17.8235(5) _cell_length_b 17.5400(3) _cell_length_c 16.1051(4) _cell_angle_alpha 90.00 _cell_angle_beta 120.0570(10) _cell_angle_gamma 90.00 _cell_volume 4357.79(18) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17616 _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.992 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2496 _exptl_absorpt_coefficient_mu 7.445 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2912 _exptl_absorpt_correction_T_max 0.7072 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_reflns_number 24328 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.56 _reflns_number_total 5003 _reflns_number_gt 4280 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'DIRDIF08 (Beurskens et al, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+24.5455P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5003 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0728 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 C1 C 0.1678(3) 0.2649(3) 0.1982(3) 0.0205(10) Uani 1 1 d . . . C2 C 0.1678(3) 0.1447(3) 0.2987(4) 0.0237(11) Uani 1 1 d . . . C3 C 0.3213(3) 0.2160(3) 0.3431(3) 0.0196(10) Uani 1 1 d . . . C4 C 0.2724(3) 0.0506(2) 0.1307(3) 0.0135(9) Uani 1 1 d . . . C5 C 0.1747(3) 0.0605(2) 0.0650(3) 0.0143(9) Uani 1 1 d . . . C6 C 0.1275(3) 0.0291(3) -0.0267(3) 0.0182(10) Uani 1 1 d . . . H6 H 0.1547 -0.0039 -0.0503 0.022 Uiso 1 1 calc R . . C7 C 0.0406(3) 0.0468(3) -0.0827(3) 0.0197(10) Uani 1 1 d . . . H7 H 0.0072 0.0259 -0.1453 0.024 Uiso 1 1 calc R . . C8 C 0.0026(3) 0.0957(3) -0.0463(3) 0.0206(10) Uani 1 1 d . . . H8 H -0.0575 0.1072 -0.0828 0.025 Uiso 1 1 calc R . . C9 C 0.0530(3) 0.1270(3) 0.0431(3) 0.0185(10) Uani 1 1 d . . . H9 H 0.0268 0.1611 0.0670 0.022 Uiso 1 1 calc R . . C10 C 0.3100(3) 0.1229(3) 0.1118(3) 0.0159(9) Uani 1 1 d . . . C11 C 0.3453(3) 0.1273(3) 0.0537(3) 0.0224(10) Uani 1 1 d . . . H11 H 0.3477 0.0834 0.0205 0.027 Uiso 1 1 calc R . . C12 C 0.3776(3) 0.1966(3) 0.0438(4) 0.0241(11) Uani 1 1 d . . . H12 H 0.4040 0.2006 0.0054 0.029 Uiso 1 1 calc R . . C13 C 0.3705(3) 0.2600(3) 0.0913(4) 0.0270(12) Uani 1 1 d . . . H13 H 0.3943 0.3076 0.0878 0.032 Uiso 1 1 calc R . . C14 C 0.3286(3) 0.2534(3) 0.1434(3) 0.0225(11) Uani 1 1 d . . . H14 H 0.3214 0.2974 0.1732 0.027 Uiso 1 1 calc R . . C15 C 0.3759(3) 0.0583(3) 0.3092(3) 0.0193(10) Uani 1 1 d . . . C16 C 0.3870(4) 0.0311(3) 0.4033(3) 0.0312(12) Uani 1 1 d . . . H16A H 0.3963 -0.0242 0.4086 0.047 Uiso 1 1 calc R . . H16B H 0.3348 0.0433 0.4065 0.047 Uiso 1 1 calc R . . H16C H 0.4372 0.0565 0.4562 0.047 Uiso 1 1 calc R . . C17 C 0.30934(18) -0.02619(12) 0.1206(2) 0.0147(9) Uani 1 1 d G . . C18 C 0.39404(17) -0.03084(13) 0.1385(2) 0.0182(10) Uani 1 1 d G . . H18 H 0.4293 0.0135 0.1564 0.022 Uiso 1 1 calc R . . C19 C 0.42708(15) -0.10040(16) 0.1302(2) 0.0237(11) Uani 1 1 d G . . H19 H 0.4850 -0.1036 0.1425 0.028 Uiso 1 1 calc R . . C20 C 0.3754(2) -0.16530(12) 0.1040(2) 0.0232(11) Uani 1 1 d G . . H20 H 0.3980 -0.2128 0.0983 0.028 Uiso 1 1 calc R . . C21 C 0.29075(19) -0.16064(12) 0.0861(2) 0.0229(11) Uani 1 1 d G . . H21 H 0.2555 -0.2050 0.0682 0.027 Uiso 1 1 calc R . . C22 C 0.25770(15) -0.09109(15) 0.0944(2) 0.0187(10) Uani 1 1 d G . . H22 H 0.1998 -0.0879 0.0821 0.022 Uiso 1 1 calc R . . N1 N 0.2871(2) 0.0573(2) 0.2321(3) 0.0147(8) Uani 1 1 d . . . N2 N 0.2977(3) 0.1861(2) 0.1529(3) 0.0169(8) Uani 1 1 d . . . N3 N 0.1384(2) 0.1114(2) 0.0984(3) 0.0145(8) Uani 1 1 d . . . O1 O 0.1278(2) 0.32069(19) 0.1748(3) 0.0280(8) Uani 1 1 d . . . O2 O 0.1313(3) 0.1329(2) 0.3396(3) 0.0313(9) Uani 1 1 d . . . O3 O 0.3789(2) 0.2434(2) 0.4100(2) 0.0296(8) Uani 1 1 d . . . O4 O 0.4344(2) 0.07860(18) 0.2982(2) 0.0235(7) Uani 1 1 d . . . Br1 Br 0.17680(3) -0.05740(3) 0.28135(3) 0.02387(12) Uani 1 1 d . . . Re1 Re 0.228430(12) 0.169811(9) 0.230630(12) 0.01534(7) Uani 1 1 d . . . H1 H 0.251(3) 0.010(3) 0.249(3) 0.019(12) Uiso 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 0.018(3) 0.028(3) 0.013(2) -0.0048(19) 0.007(2) -0.003(2) C2 0.029(3) 0.017(2) 0.022(3) -0.0031(19) 0.011(2) 0.002(2) C3 0.029(3) 0.014(2) 0.023(2) 0.0015(19) 0.019(2) 0.006(2) C4 0.017(2) 0.013(2) 0.011(2) 0.0018(16) 0.0069(18) 0.0030(17) C5 0.015(2) 0.013(2) 0.017(2) 0.0054(17) 0.0100(19) 0.0037(17) C6 0.022(3) 0.016(2) 0.018(2) 0.0032(18) 0.011(2) -0.0013(19) C7 0.024(3) 0.019(2) 0.017(2) 0.0018(18) 0.011(2) -0.001(2) C8 0.014(2) 0.021(2) 0.023(2) 0.0049(19) 0.007(2) -0.0019(19) C9 0.019(3) 0.018(2) 0.023(2) 0.0022(19) 0.013(2) 0.0006(19) C10 0.016(2) 0.017(2) 0.014(2) -0.0016(17) 0.0062(18) 0.0009(18) C11 0.025(3) 0.019(2) 0.025(3) 0.003(2) 0.015(2) 0.004(2) C12 0.027(3) 0.026(3) 0.028(3) 0.004(2) 0.020(2) -0.003(2) C13 0.030(3) 0.020(2) 0.033(3) 0.006(2) 0.017(2) -0.002(2) C14 0.026(3) 0.011(2) 0.027(3) -0.0010(19) 0.010(2) -0.0011(19) C15 0.017(3) 0.015(2) 0.022(2) -0.0030(18) 0.007(2) 0.0027(19) C16 0.023(3) 0.043(3) 0.019(3) 0.005(2) 0.005(2) 0.003(2) C17 0.019(2) 0.012(2) 0.014(2) 0.0003(16) 0.0091(19) 0.0027(18) C18 0.019(3) 0.019(2) 0.017(2) -0.0008(18) 0.009(2) 0.0011(19) C19 0.022(3) 0.030(3) 0.021(2) 0.005(2) 0.013(2) 0.008(2) C20 0.035(3) 0.016(2) 0.022(3) 0.0022(18) 0.017(2) 0.009(2) C21 0.031(3) 0.016(2) 0.023(3) 0.0011(19) 0.015(2) -0.002(2) C22 0.019(3) 0.015(2) 0.022(2) 0.0021(18) 0.010(2) 0.0017(19) N1 0.019(2) 0.0142(18) 0.0147(18) 0.0009(14) 0.0109(16) 0.0018(15) N2 0.021(2) 0.0129(18) 0.0175(19) 0.0035(15) 0.0101(17) -0.0005(16) N3 0.014(2) 0.0137(18) 0.0167(19) 0.0036(14) 0.0080(16) 0.0005(15) O1 0.033(2) 0.0215(18) 0.030(2) 0.0048(15) 0.0160(18) 0.0144(16) O2 0.040(2) 0.031(2) 0.036(2) 0.0039(16) 0.029(2) 0.0031(17) O3 0.031(2) 0.0266(19) 0.0244(19) -0.0079(15) 0.0093(17) -0.0083(16) O4 0.0168(18) 0.0245(18) 0.0272(18) -0.0013(14) 0.0094(15) 0.0021(15) Br1 0.0266(3) 0.0210(2) 0.0251(3) 0.00323(19) 0.0138(2) -0.0028(2) Re1 0.01802(11) 0.01361(10) 0.01531(10) -0.00006(7) 0.00904(8) 0.00207(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.157(6) . ? C1 Re1 1.912(5) . ? C2 O2 1.154(6) . ? C2 Re1 1.936(5) . ? C3 O3 1.157(6) . ? C3 Re1 1.916(5) . ? C4 N1 1.524(5) . ? C4 C5 1.528(6) . ? C4 C10 1.535(6) . ? C4 C17 1.544(5) . ? C5 N3 1.362(6) . ? C5 C6 1.395(6) . ? C6 C7 1.382(7) . ? C6 H6 0.9500 . ? C7 C8 1.392(7) . ? C7 H7 0.9500 . ? C8 C9 1.373(7) . ? C8 H8 0.9500 . ? C9 N3 1.353(6) . ? C9 H9 0.9500 . ? C10 N2 1.363(6) . ? C10 C11 1.367(6) . ? C11 C12 1.388(7) . ? C11 H11 0.9500 . ? C12 C13 1.392(7) . ? C12 H12 0.9500 . ? C13 C14 1.379(7) . ? C13 H13 0.9500 . ? C14 N2 1.344(6) . ? C14 H14 0.9500 . ? C15 O4 1.197(6) . ? C15 N1 1.442(6) . ? C15 C16 1.504(7) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.3900 . ? C17 C22 1.3900 . ? C18 C19 1.3900 . ? C18 H18 0.9500 . ? C19 C20 1.3900 . ? C19 H19 0.9500 . ? C20 C21 1.3900 . ? C20 H20 0.9500 . ? C21 C22 1.3900 . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? N1 Re1 2.227(4) . ? N1 H1 1.15(5) . ? N2 Re1 2.173(4) . ? N3 Re1 2.176(4) . ? 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 176.6(4) . . ? O2 C2 Re1 177.2(4) . . ? O3 C3 Re1 178.1(4) . . ? N1 C4 C5 105.0(3) . . ? N1 C4 C10 106.9(3) . . ? C5 C4 C10 103.2(3) . . ? N1 C4 C17 109.1(3) . . ? C5 C4 C17 115.1(3) . . ? C10 C4 C17 116.6(3) . . ? N3 C5 C6 121.5(4) . . ? N3 C5 C4 113.7(4) . . ? C6 C5 C4 124.3(4) . . ? C7 C6 C5 119.2(4) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 119.0(4) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C9 C8 C7 119.2(4) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? N3 C9 C8 122.6(4) . . ? N3 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? N2 C10 C11 121.9(4) . . ? N2 C10 C4 112.5(4) . . ? C11 C10 C4 125.3(4) . . ? C10 C11 C12 119.1(4) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C11 C12 C13 118.7(5) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 119.6(4) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? N2 C14 C13 121.3(4) . . ? N2 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? O4 C15 N1 122.6(4) . . ? O4 C15 C16 124.0(4) . . ? N1 C15 C16 113.5(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 120.0 . . ? C18 C17 C4 120.4(2) . . ? C22 C17 C4 119.6(2) . . ? C19 C18 C17 120.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 120.0 . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.0 . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 C20 120.0 . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C17 120.0 . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? C15 N1 C4 116.7(4) . . ? C15 N1 Re1 107.8(3) . . ? C4 N1 Re1 103.2(2) . . ? C15 N1 H1 108(2) . . ? C4 N1 H1 112(2) . . ? Re1 N1 H1 109(2) . . ? C14 N2 C10 119.0(4) . . ? C14 N2 Re1 124.3(3) . . ? C10 N2 Re1 116.7(3) . . ? C9 N3 C5 118.3(4) . . ? C9 N3 Re1 125.7(3) . . ? C5 N3 Re1 115.6(3) . . ? C1 Re1 C3 89.52(19) . . ? C1 Re1 C2 87.3(2) . . ? C3 Re1 C2 91.4(2) . . ? C1 Re1 N2 97.74(17) . . ? C3 Re1 N2 91.03(17) . . ? C2 Re1 N2 174.40(16) . . ? C1 Re1 N3 96.02(16) . . ? C3 Re1 N3 171.19(17) . . ? C2 Re1 N3 95.71(17) . . ? N2 Re1 N3 81.47(14) . . ? C1 Re1 N1 166.78(16) . . ? C3 Re1 N1 100.71(16) . . ? C2 Re1 N1 100.62(17) . . ? N2 Re1 N1 73.95(13) . . ? N3 Re1 N1 72.86(13) . . ? 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 C4 C5 N3 35.8(4) . . . . ? C10 C4 C5 N3 -76.1(4) . . . . ? C17 C4 C5 N3 155.7(3) . . . . ? N1 C4 C5 C6 -152.5(4) . . . . ? C10 C4 C5 C6 95.6(5) . . . . ? C17 C4 C5 C6 -32.6(6) . . . . ? N3 C5 C6 C7 -3.8(6) . . . . ? C4 C5 C6 C7 -174.9(4) . . . . ? C5 C6 C7 C8 0.3(6) . . . . ? C6 C7 C8 C9 2.1(7) . . . . ? C7 C8 C9 N3 -1.1(7) . . . . ? N1 C4 C10 N2 -36.4(5) . . . . ? C5 C4 C10 N2 74.0(4) . . . . ? C17 C4 C10 N2 -158.7(4) . . . . ? N1 C4 C10 C11 149.2(4) . . . . ? C5 C4 C10 C11 -100.4(5) . . . . ? C17 C4 C10 C11 26.9(6) . . . . ? N2 C10 C11 C12 6.6(7) . . . . ? C4 C10 C11 C12 -179.5(4) . . . . ? C10 C11 C12 C13 -1.9(7) . . . . ? C11 C12 C13 C14 -2.7(8) . . . . ? C12 C13 C14 N2 3.0(8) . . . . ? N1 C4 C17 C18 -92.2(3) . . . . ? C5 C4 C17 C18 150.2(3) . . . . ? C10 C4 C17 C18 29.1(4) . . . . ? N1 C4 C17 C22 87.2(3) . . . . ? C5 C4 C17 C22 -30.5(4) . . . . ? C10 C4 C17 C22 -151.6(3) . . . . ? C22 C17 C18 C19 0.0 . . . . ? C4 C17 C18 C19 179.3(3) . . . . ? C17 C18 C19 C20 0.0 . . . . ? C18 C19 C20 C21 0.0 . . . . ? C19 C20 C21 C22 0.0 . . . . ? C20 C21 C22 C17 0.0 . . . . ? C18 C17 C22 C21 0.0 . . . . ? C4 C17 C22 C21 -179.3(3) . . . . ? O4 C15 N1 C4 24.8(6) . . . . ? C16 C15 N1 C4 -154.8(4) . . . . ? O4 C15 N1 Re1 -90.7(4) . . . . ? C16 C15 N1 Re1 89.6(4) . . . . ? C5 C4 N1 C15 -173.5(3) . . . . ? C10 C4 N1 C15 -64.3(4) . . . . ? C17 C4 N1 C15 62.6(4) . . . . ? C5 C4 N1 Re1 -55.5(3) . . . . ? C10 C4 N1 Re1 53.7(3) . . . . ? C17 C4 N1 Re1 -179.4(2) . . . . ? C13 C14 N2 C10 1.4(7) . . . . ? C13 C14 N2 Re1 -178.6(4) . . . . ? C11 C10 N2 C14 -6.3(7) . . . . ? C4 C10 N2 C14 179.0(4) . . . . ? C11 C10 N2 Re1 173.7(4) . . . . ? C4 C10 N2 Re1 -0.9(5) . . . . ? C8 C9 N3 C5 -2.3(6) . . . . ? C8 C9 N3 Re1 170.3(3) . . . . ? C6 C5 N3 C9 4.7(6) . . . . ? C4 C5 N3 C9 176.7(4) . . . . ? C6 C5 N3 Re1 -168.6(3) . . . . ? C4 C5 N3 Re1 3.4(4) . . . . ? O1 C1 Re1 C3 -177(100) . . . . ? O1 C1 Re1 C2 -86(7) . . . . ? O1 C1 Re1 N2 92(7) . . . . ? O1 C1 Re1 N3 10(7) . . . . ? O1 C1 Re1 N1 42(8) . . . . ? O3 C3 Re1 C1 -121(13) . . . . ? O3 C3 Re1 C2 151(13) . . . . ? O3 C3 Re1 N2 -24(13) . . . . ? O3 C3 Re1 N3 8(13) . . . . ? O3 C3 Re1 N1 50(13) . . . . ? O2 C2 Re1 C1 -25(9) . . . . ? O2 C2 Re1 C3 65(9) . . . . ? O2 C2 Re1 N2 180(100) . . . . ? O2 C2 Re1 N3 -121(9) . . . . ? O2 C2 Re1 N1 166(9) . . . . ? C14 N2 Re1 C1 35.5(4) . . . . ? C10 N2 Re1 C1 -144.6(3) . . . . ? C14 N2 Re1 C3 -54.2(4) . . . . ? C10 N2 Re1 C3 125.7(3) . . . . ? C14 N2 Re1 C2 -169.5(17) . . . . ? C10 N2 Re1 C2 10(2) . . . . ? C14 N2 Re1 N3 130.4(4) . . . . ? C10 N2 Re1 N3 -49.6(3) . . . . ? C14 N2 Re1 N1 -155.1(4) . . . . ? C10 N2 Re1 N1 24.9(3) . . . . ? C9 N3 Re1 C1 -27.8(4) . . . . ? C5 N3 Re1 C1 144.9(3) . . . . ? C9 N3 Re1 C3 -156.6(10) . . . . ? C5 N3 Re1 C3 16.2(12) . . . . ? C9 N3 Re1 C2 60.1(4) . . . . ? C5 N3 Re1 C2 -127.2(3) . . . . ? C9 N3 Re1 N2 -124.8(4) . . . . ? C5 N3 Re1 N2 48.0(3) . . . . ? C9 N3 Re1 N1 159.5(4) . . . . ? C5 N3 Re1 N1 -27.8(3) . . . . ? C15 N1 Re1 C1 134.9(7) . . . . ? C4 N1 Re1 C1 10.9(9) . . . . ? C15 N1 Re1 C3 -5.3(3) . . . . ? C4 N1 Re1 C3 -129.4(3) . . . . ? C15 N1 Re1 C2 -98.7(3) . . . . ? C4 N1 Re1 C2 137.2(3) . . . . ? C15 N1 Re1 N2 82.7(3) . . . . ? C4 N1 Re1 N2 -41.4(3) . . . . ? C15 N1 Re1 N3 168.5(3) . . . . ? C4 N1 Re1 N3 44.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Br1 1.15(5) 2.03(5) 3.178(4) 170(4) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.675 _refine_diff_density_min -1.309 _refine_diff_density_rms 0.166 # Attachment '- 8c_CCDC821719.cif' data_pd-9-84 _database_code_depnum_ccdc_archive 'CCDC 821719' #TrackingRef '- 8c_CCDC821719.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22.50 H17 Cl N3 O4 Re' _chemical_formula_weight 615.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 1 2/n 1' _symmetry_space_group_name_Hall '-P 2yac' _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 14.2033(7) _cell_length_b 11.9057(5) _cell_length_c 26.0996(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.1430(10) _cell_angle_gamma 90.00 _cell_volume 4410.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9502 _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2376 _exptl_absorpt_coefficient_mu 5.666 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2102 _exptl_absorpt_correction_T_max 0.5496 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 19785 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7984 _reflns_number_gt 7173 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'DIRDIF08 (Beurskens et al, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0733P)^2^+39.6572P] 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 7984 _refine_ls_number_parameters 547 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1392 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.062 _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 C1A C 0.4594(6) 0.5527(6) 0.3392(3) 0.0286(17) Uani 1 1 d . . . C2A C 0.2821(5) 0.4853(6) 0.3485(3) 0.0266(16) Uani 1 1 d . . . C3A C 0.3971(6) 0.5153(6) 0.4346(3) 0.0285(17) Uani 1 1 d . . . C4A C 0.4266(5) 0.1835(6) 0.3798(3) 0.0188(14) Uani 1 1 d . . . C5A C 0.4052(5) 0.1977(6) 0.3213(3) 0.0182(14) Uani 1 1 d . . . C6A C 0.3845(5) 0.1148(7) 0.2856(3) 0.0242(15) Uani 1 1 d . . . H6A H 0.3825 0.0382 0.2957 0.029 Uiso 1 1 calc R . . C7A C 0.3665(5) 0.1451(7) 0.2349(3) 0.0236(15) Uani 1 1 d . . . H7A H 0.3517 0.0893 0.2099 0.028 Uiso 1 1 calc R . . C8A C 0.3703(5) 0.2569(7) 0.2210(3) 0.0268(16) Uani 1 1 d . . . H8A H 0.3612 0.2792 0.1862 0.032 Uiso 1 1 calc R . . C9A C 0.3875(5) 0.3350(7) 0.2589(3) 0.0243(16) Uani 1 1 d . . . H9A H 0.3885 0.4122 0.2497 0.029 Uiso 1 1 calc R . . C10A C 0.5275(5) 0.2298(5) 0.3894(2) 0.0156(13) Uani 1 1 d . . . C11A C 0.6073(5) 0.1638(6) 0.3943(3) 0.0200(14) Uani 1 1 d . . . H11A H 0.6028 0.0845 0.3914 0.024 Uiso 1 1 calc R . . C12A C 0.6940(5) 0.2148(6) 0.4035(3) 0.0238(15) Uani 1 1 d . . . H12A H 0.7496 0.1706 0.4065 0.029 Uiso 1 1 calc R . . C13A C 0.6993(5) 0.3306(6) 0.4082(3) 0.0240(15) Uani 1 1 d . . . H13A H 0.7579 0.3666 0.4157 0.029 Uiso 1 1 calc R . . C14A C 0.6166(5) 0.3927(6) 0.4016(3) 0.0246(15) Uani 1 1 d . . . H14A H 0.6194 0.4723 0.4040 0.029 Uiso 1 1 calc R . . C15A C 0.2687(5) 0.2388(6) 0.4025(2) 0.0203(14) Uani 1 1 d . . . C16A C 0.2044(5) 0.3139(7) 0.4317(3) 0.0259(16) Uani 1 1 d . . . H16C H 0.1620 0.3541 0.4076 0.039 Uiso 1 1 calc R . . H16D H 0.2421 0.3681 0.4519 0.039 Uiso 1 1 calc R . . H16E H 0.1672 0.2682 0.4548 0.039 Uiso 1 1 calc R . . C17A C 0.4211(3) 0.0650(3) 0.40402(15) 0.0202(14) Uani 1 1 d G . . C22A C 0.4550(3) -0.0308(4) 0.38049(14) 0.0220(15) Uani 1 1 d G . . H22A H 0.4780 -0.0264 0.3469 0.026 Uiso 1 1 calc R . . C21A C 0.4551(4) -0.1331(3) 0.40620(18) 0.0326(19) Uani 1 1 d G . . H21A H 0.4782 -0.1986 0.3901 0.039 Uiso 1 1 calc R . . C20A C 0.4213(4) -0.1395(3) 0.45542(18) 0.036(2) Uani 1 1 d G . . H20A H 0.4214 -0.2094 0.4730 0.044 Uiso 1 1 calc R . . C19A C 0.3875(4) -0.0437(4) 0.47895(13) 0.0304(18) Uani 1 1 d G . . H19A H 0.3644 -0.0481 0.5126 0.036 Uiso 1 1 calc R . . C18A C 0.3874(3) 0.0586(3) 0.45324(15) 0.0234(15) Uani 1 1 d G . . H18A H 0.3642 0.1241 0.4693 0.028 Uiso 1 1 calc R . . O1A O 0.4946(4) 0.6281(5) 0.3199(3) 0.0431(15) Uani 1 1 d . . . O2A O 0.2125(4) 0.5198(5) 0.3305(2) 0.0315(12) Uani 1 1 d . . . O3A O 0.3925(5) 0.5663(5) 0.4717(2) 0.0403(15) Uani 1 1 d . . . O4A O 0.2363(3) 0.1540(4) 0.38101(19) 0.0228(11) Uani 1 1 d . . . N1A N 0.3627(4) 0.2675(5) 0.4039(2) 0.0193(12) Uani 1 1 d . . . N2A N 0.5333(4) 0.3430(5) 0.3920(2) 0.0166(11) Uani 1 1 d . . . N3A N 0.4030(4) 0.3071(5) 0.3083(2) 0.0187(12) Uani 1 1 d . . . Re1A Re 0.402310(18) 0.42763(2) 0.372439(9) 0.01680(11) Uani 1 1 d . . . C1B C 0.5409(5) 0.5538(6) 0.1655(3) 0.0233(15) Uani 1 1 d . . . C3B C 0.5988(5) 0.5907(6) 0.0691(3) 0.0245(16) Uani 1 1 d . . . C2B C 0.7169(5) 0.6172(6) 0.1529(3) 0.0232(15) Uani 1 1 d . . . C15B C 0.7274(5) 0.8704(6) 0.0976(2) 0.0170(13) Uani 1 1 d . . . C16B C 0.7908(5) 0.7910(7) 0.0699(3) 0.0274(16) Uani 1 1 d . . . H16F H 0.8298 0.8338 0.0466 0.041 Uiso 1 1 calc R . . H16G H 0.7522 0.7368 0.0501 0.041 Uiso 1 1 calc R . . H16H H 0.8315 0.7508 0.0949 0.041 Uiso 1 1 calc R . . C4B C 0.5732(5) 0.9223(6) 0.1243(2) 0.0168(14) Uani 1 1 d . . . C5B C 0.5981(5) 0.9081(6) 0.1824(3) 0.0208(15) Uani 1 1 d . . . C6B C 0.6194(5) 0.9912(6) 0.2188(3) 0.0245(16) Uani 1 1 d . . . H6B H 0.6208 1.0681 0.2091 0.029 Uiso 1 1 calc R . . C7B C 0.6383(5) 0.9599(7) 0.2691(3) 0.0276(17) Uani 1 1 d . . . H7B H 0.6547 1.0152 0.2941 0.033 Uiso 1 1 calc R . . C8B C 0.6336(5) 0.8483(7) 0.2831(3) 0.0280(17) Uani 1 1 d . . . H8B H 0.6425 0.8262 0.3179 0.034 Uiso 1 1 calc R . . C9B C 0.6155(5) 0.7695(6) 0.2451(3) 0.0231(15) Uani 1 1 d . . . H9B H 0.6146 0.6922 0.2540 0.028 Uiso 1 1 calc R . . C10B C 0.4722(5) 0.8776(6) 0.1168(2) 0.0184(14) Uani 1 1 d . . . C11B C 0.3913(5) 0.9443(6) 0.1139(3) 0.0214(15) Uani 1 1 d . . . H11B H 0.3961 1.0237 0.1159 0.026 Uiso 1 1 calc R . . C12B C 0.3039(5) 0.8932(7) 0.1081(3) 0.0281(16) Uani 1 1 d . . . H12B H 0.2481 0.9372 0.1073 0.034 Uiso 1 1 calc R . . C13B C 0.2984(5) 0.7776(6) 0.1034(3) 0.0267(16) Uani 1 1 d . . . H13B H 0.2394 0.7416 0.0973 0.032 Uiso 1 1 calc R . . C14B C 0.3807(5) 0.7152(6) 0.1078(3) 0.0239(15) Uani 1 1 d . . . H14B H 0.3771 0.6356 0.1059 0.029 Uiso 1 1 calc R . . C17B C 0.5750(3) 1.0418(3) 0.09989(15) 0.0196(14) Uani 1 1 d G . . C18B C 0.5956(3) 1.0481(3) 0.04834(15) 0.0231(15) Uani 1 1 d G . . H18B H 0.6141 0.9825 0.0306 0.028 Uiso 1 1 calc R . . C19B C 0.5893(4) 1.1504(4) 0.02276(12) 0.0283(17) Uani 1 1 d G . . H19B H 0.6035 1.1547 -0.0125 0.034 Uiso 1 1 calc R . . C20B C 0.5623(4) 1.2464(3) 0.04873(17) 0.0297(18) Uani 1 1 d G . . H20B H 0.5580 1.3163 0.0312 0.036 Uiso 1 1 calc R . . C21B C 0.5416(4) 1.2401(3) 0.10029(17) 0.0277(17) Uani 1 1 d G . . H21B H 0.5232 1.3057 0.1180 0.033 Uiso 1 1 calc R . . C22B C 0.5479(3) 1.1378(4) 0.12587(13) 0.0251(16) Uani 1 1 d G . . H22B H 0.5338 1.1335 0.1611 0.030 Uiso 1 1 calc R . . O1B O 0.5084(4) 0.4787(5) 0.1859(2) 0.0391(14) Uani 1 1 d . . . O2B O 0.7864(4) 0.5795(5) 0.1693(2) 0.0334(13) Uani 1 1 d . . . O3B O 0.6018(4) 0.5398(5) 0.0317(2) 0.0368(14) Uani 1 1 d . . . O4B O 0.7612(4) 0.9584(4) 0.11577(19) 0.0232(11) Uani 1 1 d . . . N1B N 0.6358(4) 0.8402(5) 0.0992(2) 0.0167(11) Uani 1 1 d . . . N2B N 0.4662(4) 0.7647(5) 0.1146(2) 0.0179(12) Uani 1 1 d . . . N3B N 0.5991(4) 0.7991(5) 0.1954(2) 0.0201(12) Uani 1 1 d . . . Re1B Re 0.596787(17) 0.67896(2) 0.131160(9) 0.01629(11) Uani 1 1 d . . . Cl1A Cl 0.3536(3) -0.1846(4) 0.24609(15) 0.1043(15) Uani 1 1 d D . . C23A C 0.2500 -0.260(2) 0.2500 0.109(8) Uani 1 2 d SDU . . H23A H 0.2560 -0.3096 0.2805 0.131 Uiso 0.50 1 calc PR . . H23B H 0.2440 -0.3096 0.2195 0.131 Uiso 0.50 1 calc PR . . Cl1B Cl 0.6502(2) 1.2886(3) 0.26396(13) 0.0769(9) Uani 1 1 d D . . C23B C 0.7500 1.357(3) 0.2500 0.157(12) Uani 1 2 d SDU . . H23C H 0.7658 1.4062 0.2795 0.188 Uiso 0.50 1 calc PR . . H23D H 0.7342 1.4062 0.2205 0.188 Uiso 0.50 1 calc PR . . 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 C1A 0.031(4) 0.018(4) 0.036(4) 0.001(3) -0.007(3) 0.011(3) C2A 0.026(4) 0.021(4) 0.033(4) 0.004(3) 0.001(3) 0.001(3) C3A 0.031(4) 0.024(4) 0.030(4) 0.012(3) -0.001(3) -0.001(3) C4A 0.022(4) 0.018(4) 0.016(3) -0.003(2) -0.001(3) 0.006(3) C5A 0.014(3) 0.025(4) 0.015(3) -0.006(3) -0.006(3) 0.003(3) C6A 0.027(4) 0.027(4) 0.019(3) -0.002(3) -0.003(3) 0.004(3) C7A 0.019(4) 0.032(4) 0.020(3) -0.005(3) 0.002(3) 0.002(3) C8A 0.024(4) 0.041(5) 0.015(3) 0.001(3) -0.004(3) 0.003(3) C9A 0.020(4) 0.033(4) 0.020(3) 0.010(3) 0.000(3) -0.003(3) C10A 0.020(3) 0.017(3) 0.011(3) 0.000(2) 0.002(2) -0.004(3) C11A 0.021(4) 0.023(4) 0.016(3) 0.001(3) -0.004(3) 0.002(3) C12A 0.021(4) 0.027(4) 0.023(3) 0.008(3) -0.004(3) 0.002(3) C13A 0.021(4) 0.022(4) 0.029(4) 0.000(3) -0.003(3) -0.006(3) C14A 0.025(4) 0.023(4) 0.025(4) -0.001(3) -0.005(3) -0.003(3) C15A 0.026(4) 0.021(3) 0.014(3) 0.008(3) -0.006(3) -0.002(3) C16A 0.019(4) 0.036(4) 0.022(3) -0.002(3) -0.001(3) 0.001(3) C17A 0.021(4) 0.019(3) 0.019(3) 0.004(3) -0.004(3) -0.004(3) C22A 0.022(4) 0.017(3) 0.027(4) 0.001(3) -0.003(3) -0.004(3) C21A 0.028(4) 0.022(4) 0.046(5) 0.000(3) -0.016(4) 0.001(3) C20A 0.038(5) 0.021(4) 0.048(5) 0.012(4) -0.025(4) -0.002(3) C19A 0.041(5) 0.028(4) 0.021(3) 0.011(3) -0.012(3) -0.008(3) C18A 0.030(4) 0.023(4) 0.016(3) 0.005(3) -0.011(3) -0.001(3) O1A 0.039(4) 0.031(3) 0.059(4) 0.015(3) 0.007(3) -0.004(3) O2A 0.029(3) 0.031(3) 0.034(3) -0.001(2) -0.007(2) 0.010(2) O3A 0.064(4) 0.032(3) 0.024(3) -0.012(2) -0.002(3) -0.004(3) O4A 0.024(3) 0.022(3) 0.022(2) 0.000(2) -0.010(2) -0.003(2) N1A 0.021(3) 0.018(3) 0.019(3) -0.003(2) -0.001(2) 0.003(2) N2A 0.018(3) 0.018(3) 0.014(3) 0.002(2) 0.002(2) -0.001(2) N3A 0.021(3) 0.021(3) 0.014(3) 0.000(2) -0.002(2) 0.003(2) Re1A 0.01784(18) 0.01522(17) 0.01716(16) 0.00108(9) -0.00197(11) 0.00127(9) C1B 0.025(4) 0.012(3) 0.032(4) 0.002(3) -0.005(3) 0.005(3) C3B 0.025(4) 0.024(4) 0.024(4) 0.007(3) -0.004(3) -0.004(3) C2B 0.023(4) 0.020(4) 0.027(4) -0.001(3) 0.004(3) -0.001(3) C15B 0.023(3) 0.020(3) 0.008(3) 0.002(2) -0.002(2) 0.000(3) C16B 0.024(4) 0.037(4) 0.022(3) -0.003(3) 0.011(3) -0.011(3) C4B 0.021(3) 0.021(4) 0.008(3) 0.000(2) -0.001(2) -0.013(3) C5B 0.022(4) 0.023(4) 0.017(3) -0.001(3) -0.006(3) -0.003(3) C6B 0.028(4) 0.021(4) 0.025(4) -0.004(3) -0.008(3) 0.003(3) C7B 0.024(4) 0.041(5) 0.017(3) -0.006(3) -0.003(3) 0.000(3) C8B 0.027(4) 0.044(5) 0.012(3) 0.007(3) -0.003(3) 0.002(4) C9B 0.023(4) 0.028(4) 0.018(3) 0.010(3) -0.001(3) -0.004(3) C10B 0.021(3) 0.024(4) 0.010(3) -0.001(2) -0.003(2) 0.000(3) C11B 0.023(4) 0.023(4) 0.017(3) 0.005(3) -0.010(3) -0.002(3) C12B 0.024(4) 0.027(4) 0.033(4) 0.004(3) -0.003(3) 0.001(3) C13B 0.016(3) 0.024(4) 0.040(4) 0.005(3) -0.005(3) -0.002(3) C14B 0.029(4) 0.021(4) 0.021(3) 0.004(3) -0.004(3) -0.004(3) C17B 0.014(3) 0.023(4) 0.021(3) -0.001(3) -0.007(3) -0.002(3) C18B 0.029(4) 0.019(3) 0.020(3) 0.002(3) -0.011(3) -0.002(3) C19B 0.037(4) 0.030(4) 0.017(3) 0.006(3) -0.012(3) -0.002(3) C20B 0.031(4) 0.018(4) 0.038(4) 0.009(3) -0.019(3) -0.006(3) C21B 0.024(4) 0.022(4) 0.036(4) 0.000(3) -0.009(3) 0.000(3) C22B 0.032(4) 0.016(3) 0.027(4) -0.001(3) -0.005(3) 0.001(3) O1B 0.040(3) 0.030(3) 0.048(4) 0.011(3) 0.004(3) 0.001(3) O2B 0.025(3) 0.030(3) 0.044(3) -0.005(2) -0.011(3) 0.010(2) O3B 0.054(4) 0.032(3) 0.024(3) -0.014(2) 0.000(3) -0.005(3) O4B 0.025(3) 0.023(3) 0.022(2) 0.002(2) -0.009(2) -0.008(2) N1B 0.021(3) 0.016(3) 0.013(2) -0.001(2) 0.001(2) -0.005(2) N2B 0.021(3) 0.020(3) 0.012(2) 0.003(2) -0.003(2) 0.001(2) N3B 0.024(3) 0.018(3) 0.018(3) 0.000(2) -0.005(2) 0.003(2) Re1B 0.01663(18) 0.01598(18) 0.01598(15) 0.00182(9) -0.00330(11) -0.00032(9) Cl1A 0.109(3) 0.130(4) 0.072(2) -0.032(2) -0.033(2) 0.048(3) C23A 0.133(11) 0.091(10) 0.107(11) 0.000 0.044(9) 0.000 Cl1B 0.073(2) 0.097(2) 0.0601(18) -0.0210(17) -0.0059(15) 0.0093(18) C23B 0.159(15) 0.145(14) 0.169(15) 0.000 0.040(10) 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1A O1A 1.152(10) . ? C1A Re1A 1.919(8) . ? C2A O2A 1.154(9) . ? C2A Re1A 1.923(7) . ? C3A O3A 1.147(10) . ? C3A Re1A 1.932(8) . ? C4A N1A 1.504(9) . ? C4A C10A 1.547(10) . ? C4A C17A 1.549(7) . ? C4A C5A 1.555(9) . ? C5A N3A 1.346(9) . ? C5A C6A 1.381(9) . ? C6A C7A 1.387(10) . ? C6A H6A 0.9500 . ? C7A C8A 1.381(11) . ? C7A H7A 0.9500 . ? C8A C9A 1.372(11) . ? C8A H8A 0.9500 . ? C9A N3A 1.342(9) . ? C9A H9A 0.9500 . ? C10A N2A 1.351(8) . ? C10A C11A 1.382(10) . ? C11A C12A 1.385(10) . ? C11A H11A 0.9500 . ? C12A C13A 1.385(10) . ? C12A H12A 0.9500 . ? C13A C14A 1.393(10) . ? C13A H13A 0.9500 . ? C14A N2A 1.339(9) . ? C14A H14A 0.9500 . ? C15A O4A 1.236(8) . ? C15A N1A 1.377(9) . ? C15A C16A 1.505(10) . ? C16A H16C 0.9800 . ? C16A H16D 0.9800 . ? C16A H16E 0.9800 . ? C17A C22A 1.3900 . ? C17A C18A 1.3900 . ? C22A C21A 1.3900 . ? C22A H22A 0.9500 . ? C21A C20A 1.3900 . ? C21A H21A 0.9500 . ? C20A C19A 1.3900 . ? C20A H20A 0.9500 . ? C19A C18A 1.3900 . ? C19A H19A 0.9500 . ? C18A H18A 0.9500 . ? N1A Re1A 2.159(6) . ? N2A Re1A 2.160(6) . ? N3A Re1A 2.205(6) . ? C1B O1B 1.147(9) . ? C1B Re1B 1.925(7) . ? C3B O3B 1.152(9) . ? C3B Re1B 1.931(8) . ? C2B O2B 1.152(9) . ? C2B Re1B 1.924(7) . ? C15B O4B 1.239(8) . ? C15B N1B 1.352(9) . ? C15B C16B 1.509(10) . ? C16B H16F 0.9800 . ? C16B H16G 0.9800 . ? C16B H16H 0.9800 . ? C4B N1B 1.490(9) . ? C4B C10B 1.536(9) . ? C4B C5B 1.554(9) . ? C4B C17B 1.560(7) . ? C5B N3B 1.341(9) . ? C5B C6B 1.396(9) . ? C6B C7B 1.382(10) . ? C6B H6B 0.9500 . ? C7B C8B 1.380(11) . ? C7B H7B 0.9500 . ? C8B C9B 1.383(11) . ? C8B H8B 0.9500 . ? C9B N3B 1.354(9) . ? C9B H9B 0.9500 . ? C10B N2B 1.348(9) . ? C10B C11B 1.396(10) . ? C11B C12B 1.386(10) . ? C11B H11B 0.9500 . ? C12B C13B 1.383(11) . ? C12B H12B 0.9500 . ? C13B C14B 1.386(10) . ? C13B H13B 0.9500 . ? C14B N2B 1.355(9) . ? C14B H14B 0.9500 . ? C17B C18B 1.3900 . ? C17B C22B 1.3900 . ? C18B C19B 1.3900 . ? C18B H18B 0.9500 . ? C19B C20B 1.3900 . ? C19B H19B 0.9500 . ? C20B C21B 1.3900 . ? C20B H20B 0.9500 . ? C21B C22B 1.3900 . ? C21B H21B 0.9500 . ? C22B H22B 0.9500 . ? N1B Re1B 2.173(5) . ? N2B Re1B 2.147(5) . ? N3B Re1B 2.203(6) . ? Cl1A C23A 1.731(13) . ? C23A Cl1A 1.731(13) 2 ? C23A H23A 0.9900 . ? C23A H23B 0.9900 . ? Cl1B C23B 1.684(15) . ? C23B Cl1B 1.684(15) 2_655 ? C23B H23C 0.9900 . ? C23B H23D 0.9900 . ? 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 O1A C1A Re1A 178.9(7) . . ? O2A C2A Re1A 174.9(7) . . ? O3A C3A Re1A 178.7(8) . . ? N1A C4A C10A 105.4(5) . . ? N1A C4A C17A 113.3(5) . . ? C10A C4A C17A 108.6(5) . . ? N1A C4A C5A 103.9(5) . . ? C10A C4A C5A 105.4(5) . . ? C17A C4A C5A 119.2(5) . . ? N3A C5A C6A 121.2(6) . . ? N3A C5A C4A 110.8(5) . . ? C6A C5A C4A 127.8(6) . . ? C5A C6A C7A 119.0(7) . . ? C5A C6A H6A 120.5 . . ? C7A C6A H6A 120.5 . . ? C8A C7A C6A 119.6(7) . . ? C8A C7A H7A 120.2 . . ? C6A C7A H7A 120.2 . . ? C9A C8A C7A 118.1(7) . . ? C9A C8A H8A 120.9 . . ? C7A C8A H8A 120.9 . . ? N3A C9A C8A 122.9(7) . . ? N3A C9A H9A 118.6 . . ? C8A C9A H9A 118.6 . . ? N2A C10A C11A 120.9(6) . . ? N2A C10A C4A 114.7(6) . . ? C11A C10A C4A 124.4(6) . . ? C10A C11A C12A 119.2(7) . . ? C10A C11A H11A 120.4 . . ? C12A C11A H11A 120.4 . . ? C11A C12A C13A 119.8(7) . . ? C11A C12A H12A 120.1 . . ? C13A C12A H12A 120.1 . . ? C12A C13A C14A 118.3(7) . . ? C12A C13A H13A 120.8 . . ? C14A C13A H13A 120.8 . . ? N2A C14A C13A 121.6(7) . . ? N2A C14A H14A 119.2 . . ? C13A C14A H14A 119.2 . . ? O4A C15A N1A 124.0(7) . . ? O4A C15A C16A 119.5(6) . . ? N1A C15A C16A 116.4(6) . . ? C15A C16A H16C 109.5 . . ? C15A C16A H16D 109.5 . . ? H16C C16A H16D 109.5 . . ? C15A C16A H16E 109.5 . . ? H16C C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? C22A C17A C18A 120.0 . . ? C22A C17A C4A 123.0(4) . . ? C18A C17A C4A 116.8(4) . . ? C17A C22A C21A 120.0 . . ? C17A C22A H22A 120.0 . . ? C21A C22A H22A 120.0 . . ? C20A C21A C22A 120.0 . . ? C20A C21A H21A 120.0 . . ? C22A C21A H21A 120.0 . . ? C21A C20A C19A 120.0 . . ? C21A C20A H20A 120.0 . . ? C19A C20A H20A 120.0 . . ? C20A C19A C18A 120.0 . . ? C20A C19A H19A 120.0 . . ? C18A C19A H19A 120.0 . . ? C19A C18A C17A 120.0 . . ? C19A C18A H18A 120.0 . . ? C17A C18A H18A 120.0 . . ? C15A N1A C4A 115.0(6) . . ? C15A N1A Re1A 118.4(4) . . ? C4A N1A Re1A 104.9(4) . . ? C14A N2A C10A 120.1(6) . . ? C14A N2A Re1A 125.8(5) . . ? C10A N2A Re1A 113.8(4) . . ? C9A N3A C5A 118.9(6) . . ? C9A N3A Re1A 124.3(5) . . ? C5A N3A Re1A 116.0(4) . . ? C1A Re1A C2A 87.8(3) . . ? C1A Re1A C3A 89.5(3) . . ? C2A Re1A C3A 91.1(3) . . ? C1A Re1A N1A 168.0(3) . . ? C2A Re1A N1A 101.4(3) . . ? C3A Re1A N1A 98.0(3) . . ? C1A Re1A N2A 95.4(3) . . ? C2A Re1A N2A 171.8(3) . . ? C3A Re1A N2A 96.5(3) . . ? N1A Re1A N2A 74.5(2) . . ? C1A Re1A N3A 98.5(3) . . ? C2A Re1A N3A 90.8(3) . . ? C3A Re1A N3A 171.9(3) . . ? N1A Re1A N3A 73.9(2) . . ? N2A Re1A N3A 81.2(2) . . ? O1B C1B Re1B 179.3(7) . . ? O3B C3B Re1B 178.3(7) . . ? O2B C2B Re1B 175.2(7) . . ? O4B C15B N1B 124.9(6) . . ? O4B C15B C16B 118.9(6) . . ? N1B C15B C16B 116.1(6) . . ? C15B C16B H16F 109.5 . . ? C15B C16B H16G 109.5 . . ? H16F C16B H16G 109.5 . . ? C15B C16B H16H 109.5 . . ? H16F C16B H16H 109.5 . . ? H16G C16B H16H 109.5 . . ? N1B C4B C10B 106.6(5) . . ? N1B C4B C5B 103.9(6) . . ? C10B C4B C5B 105.3(5) . . ? N1B C4B C17B 113.6(5) . . ? C10B C4B C17B 107.0(5) . . ? C5B C4B C17B 119.5(5) . . ? N3B C5B C6B 120.9(6) . . ? N3B C5B C4B 110.6(6) . . ? C6B C5B C4B 128.5(6) . . ? C7B C6B C5B 119.0(7) . . ? C7B C6B H6B 120.5 . . ? C5B C6B H6B 120.5 . . ? C8B C7B C6B 120.1(7) . . ? C8B C7B H7B 120.0 . . ? C6B C7B H7B 120.0 . . ? C7B C8B C9B 118.2(6) . . ? C7B C8B H8B 120.9 . . ? C9B C8B H8B 120.9 . . ? N3B C9B C8B 122.1(7) . . ? N3B C9B H9B 119.0 . . ? C8B C9B H9B 119.0 . . ? N2B C10B C11B 120.9(6) . . ? N2B C10B C4B 114.1(6) . . ? C11B C10B C4B 124.9(6) . . ? C12B C11B C10B 119.2(7) . . ? C12B C11B H11B 120.4 . . ? C10B C11B H11B 120.4 . . ? C13B C12B C11B 119.6(7) . . ? C13B C12B H12B 120.2 . . ? C11B C12B H12B 120.2 . . ? C12B C13B C14B 118.8(7) . . ? C12B C13B H13B 120.6 . . ? C14B C13B H13B 120.6 . . ? N2B C14B C13B 121.8(7) . . ? N2B C14B H14B 119.1 . . ? C13B C14B H14B 119.1 . . ? C18B C17B C22B 120.0 . . ? C18B C17B C4B 116.9(4) . . ? C22B C17B C4B 122.8(4) . . ? C17B C18B C19B 120.0 . . ? C17B C18B H18B 120.0 . . ? C19B C18B H18B 120.0 . . ? C20B C19B C18B 120.0 . . ? C20B C19B H19B 120.0 . . ? C18B C19B H19B 120.0 . . ? C19B C20B C21B 120.0 . . ? C19B C20B H20B 120.0 . . ? C21B C20B H20B 120.0 . . ? C22B C21B C20B 120.0 . . ? C22B C21B H21B 120.0 . . ? C20B C21B H21B 120.0 . . ? C21B C22B C17B 120.0 . . ? C21B C22B H22B 120.0 . . ? C17B C22B H22B 120.0 . . ? C15B N1B C4B 115.5(5) . . ? C15B N1B Re1B 120.4(4) . . ? C4B N1B Re1B 104.2(4) . . ? C10B N2B C14B 119.6(6) . . ? C10B N2B Re1B 114.4(4) . . ? C14B N2B Re1B 125.7(5) . . ? C5B N3B C9B 119.5(6) . . ? C5B N3B Re1B 115.8(4) . . ? C9B N3B Re1B 123.8(5) . . ? C2B Re1B C1B 86.8(3) . . ? C2B Re1B C3B 89.9(3) . . ? C1B Re1B C3B 89.3(3) . . ? C2B Re1B N2B 172.3(3) . . ? C1B Re1B N2B 95.3(3) . . ? C3B Re1B N2B 97.5(3) . . ? C2B Re1B N1B 102.4(3) . . ? C1B Re1B N1B 167.9(3) . . ? C3B Re1B N1B 98.5(3) . . ? N2B Re1B N1B 74.6(2) . . ? C2B Re1B N3B 92.0(3) . . ? C1B Re1B N3B 98.2(3) . . ? C3B Re1B N3B 172.3(3) . . ? N2B Re1B N3B 80.4(2) . . ? N1B Re1B N3B 73.9(2) . . ? Cl1A C23A Cl1A 117.3(14) . 2 ? Cl1A C23A H23A 108.0 . . ? Cl1A C23A H23A 108.0 2 . ? Cl1A C23A H23B 108.0 . . ? Cl1A C23A H23B 108.0 2 . ? H23A C23A H23B 107.2 . . ? Cl1B C23B Cl1B 122.6(19) . 2_655 ? Cl1B C23B H23C 106.7 . . ? Cl1B C23B H23C 106.7 2_655 . ? Cl1B C23B H23D 106.7 . . ? Cl1B C23B H23D 106.7 2_655 . ? H23C C23B H23D 106.6 . . ? 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 N1A C4A C5A N3A 45.9(7) . . . . ? C10A C4A C5A N3A -64.7(7) . . . . ? C17A C4A C5A N3A 173.1(6) . . . . ? N1A C4A C5A C6A -130.0(7) . . . . ? C10A C4A C5A C6A 119.4(8) . . . . ? C17A C4A C5A C6A -2.8(11) . . . . ? N3A C5A C6A C7A 3.8(11) . . . . ? C4A C5A C6A C7A 179.4(7) . . . . ? C5A C6A C7A C8A 0.4(11) . . . . ? C6A C7A C8A C9A -3.1(11) . . . . ? C7A C8A C9A N3A 1.7(11) . . . . ? N1A C4A C10A N2A -30.1(7) . . . . ? C17A C4A C10A N2A -151.8(5) . . . . ? C5A C4A C10A N2A 79.4(7) . . . . ? N1A C4A C10A C11A 151.0(6) . . . . ? C17A C4A C10A C11A 29.3(8) . . . . ? C5A C4A C10A C11A -99.5(7) . . . . ? N2A C10A C11A C12A 2.0(10) . . . . ? C4A C10A C11A C12A -179.2(6) . . . . ? C10A C11A C12A C13A 0.7(10) . . . . ? C11A C12A C13A C14A -2.3(11) . . . . ? C12A C13A C14A N2A 1.3(11) . . . . ? N1A C4A C17A C22A 163.7(4) . . . . ? C10A C4A C17A C22A -79.6(5) . . . . ? C5A C4A C17A C22A 41.0(8) . . . . ? N1A C4A C17A C18A -21.6(7) . . . . ? C10A C4A C17A C18A 95.1(5) . . . . ? C5A C4A C17A C18A -144.3(5) . . . . ? C18A C17A C22A C21A 0.0 . . . . ? C4A C17A C22A C21A 174.6(5) . . . . ? C17A C22A C21A C20A 0.0 . . . . ? C22A C21A C20A C19A 0.0 . . . . ? C21A C20A C19A C18A 0.0 . . . . ? C20A C19A C18A C17A 0.0 . . . . ? C22A C17A C18A C19A 0.0 . . . . ? C4A C17A C18A C19A -174.9(5) . . . . ? O4A C15A N1A C4A -3.6(9) . . . . ? C16A C15A N1A C4A 172.9(6) . . . . ? O4A C15A N1A Re1A 121.5(6) . . . . ? C16A C15A N1A Re1A -62.0(7) . . . . ? C10A C4A N1A C15A -176.2(5) . . . . ? C17A C4A N1A C15A -57.6(7) . . . . ? C5A C4A N1A C15A 73.2(7) . . . . ? C10A C4A N1A Re1A 51.9(5) . . . . ? C17A C4A N1A Re1A 170.5(4) . . . . ? C5A C4A N1A Re1A -58.7(5) . . . . ? C13A C14A N2A C10A 1.3(10) . . . . ? C13A C14A N2A Re1A -172.6(5) . . . . ? C11A C10A N2A C14A -3.0(9) . . . . ? C4A C10A N2A C14A 178.1(6) . . . . ? C11A C10A N2A Re1A 171.6(5) . . . . ? C4A C10A N2A Re1A -7.3(7) . . . . ? C8A C9A N3A C5A 2.4(11) . . . . ? C8A C9A N3A Re1A -167.0(6) . . . . ? C6A C5A N3A C9A -5.2(10) . . . . ? C4A C5A N3A C9A 178.6(6) . . . . ? C6A C5A N3A Re1A 165.1(6) . . . . ? C4A C5A N3A Re1A -11.2(7) . . . . ? O1A C1A Re1A C2A 135(41) . . . . ? O1A C1A Re1A C3A 44(41) . . . . ? O1A C1A Re1A N1A -85(41) . . . . ? O1A C1A Re1A N2A -53(41) . . . . ? O1A C1A Re1A N3A -135(41) . . . . ? O2A C2A Re1A C1A 54(7) . . . . ? O2A C2A Re1A C3A 144(7) . . . . ? O2A C2A Re1A N1A -118(7) . . . . ? O2A C2A Re1A N2A -59(8) . . . . ? O2A C2A Re1A N3A -44(7) . . . . ? O3A C3A Re1A C1A 146(34) . . . . ? O3A C3A Re1A C2A 58(34) . . . . ? O3A C3A Re1A N1A -44(34) . . . . ? O3A C3A Re1A N2A -119(34) . . . . ? O3A C3A Re1A N3A -46(35) . . . . ? C15A N1A Re1A C1A -140.6(12) . . . . ? C4A N1A Re1A C1A -10.7(14) . . . . ? C15A N1A Re1A C2A -1.2(5) . . . . ? C4A N1A Re1A C2A 128.7(4) . . . . ? C15A N1A Re1A C3A 91.6(5) . . . . ? C4A N1A Re1A C3A -138.5(4) . . . . ? C15A N1A Re1A N2A -173.8(5) . . . . ? C4A N1A Re1A N2A -43.9(4) . . . . ? C15A N1A Re1A N3A -88.7(5) . . . . ? C4A N1A Re1A N3A 41.2(4) . . . . ? C14A N2A Re1A C1A 30.0(6) . . . . ? C10A N2A Re1A C1A -144.3(5) . . . . ? C14A N2A Re1A C2A 142.3(18) . . . . ? C10A N2A Re1A C2A -32(2) . . . . ? C14A N2A Re1A C3A -60.1(6) . . . . ? C10A N2A Re1A C3A 125.6(5) . . . . ? C14A N2A Re1A N1A -156.6(6) . . . . ? C10A N2A Re1A N1A 29.2(4) . . . . ? C14A N2A Re1A N3A 127.8(6) . . . . ? C10A N2A Re1A N3A -46.5(4) . . . . ? C9A N3A Re1A C1A -37.0(6) . . . . ? C5A N3A Re1A C1A 153.3(5) . . . . ? C9A N3A Re1A C2A 50.9(6) . . . . ? C5A N3A Re1A C2A -118.8(5) . . . . ? C9A N3A Re1A C3A 154.6(18) . . . . ? C5A N3A Re1A C3A -15(2) . . . . ? C9A N3A Re1A N1A 152.5(6) . . . . ? C5A N3A Re1A N1A -17.2(5) . . . . ? C9A N3A Re1A N2A -131.2(6) . . . . ? C5A N3A Re1A N2A 59.1(5) . . . . ? N1B C4B C5B N3B -47.9(7) . . . . ? C10B C4B C5B N3B 64.0(7) . . . . ? C17B C4B C5B N3B -175.7(6) . . . . ? N1B C4B C5B C6B 130.8(8) . . . . ? C10B C4B C5B C6B -117.2(8) . . . . ? C17B C4B C5B C6B 3.1(11) . . . . ? N3B C5B C6B C7B -2.3(11) . . . . ? C4B C5B C6B C7B 179.1(7) . . . . ? C5B C6B C7B C8B -1.8(12) . . . . ? C6B C7B C8B C9B 4.1(11) . . . . ? C7B C8B C9B N3B -2.5(11) . . . . ? N1B C4B C10B N2B 30.7(7) . . . . ? C5B C4B C10B N2B -79.2(7) . . . . ? C17B C4B C10B N2B 152.6(5) . . . . ? N1B C4B C10B C11B -151.3(6) . . . . ? C5B C4B C10B C11B 98.7(7) . . . . ? C17B C4B C10B C11B -29.4(8) . . . . ? N2B C10B C11B C12B -0.8(10) . . . . ? C4B C10B C11B C12B -178.7(6) . . . . ? C10B C11B C12B C13B -2.3(11) . . . . ? C11B C12B C13B C14B 3.8(12) . . . . ? C12B C13B C14B N2B -2.4(11) . . . . ? N1B C4B C17B C18B 27.9(6) . . . . ? C10B C4B C17B C18B -89.5(5) . . . . ? C5B C4B C17B C18B 151.1(5) . . . . ? N1B C4B C17B C22B -158.6(4) . . . . ? C10B C4B C17B C22B 83.9(5) . . . . ? C5B C4B C17B C22B -35.5(8) . . . . ? C22B C17B C18B C19B 0.0 . . . . ? C4B C17B C18B C19B 173.6(5) . . . . ? C17B C18B C19B C20B 0.0 . . . . ? C18B C19B C20B C21B 0.0 . . . . ? C19B C20B C21B C22B 0.0 . . . . ? C20B C21B C22B C17B 0.0 . . . . ? C18B C17B C22B C21B 0.0 . . . . ? C4B C17B C22B C21B -173.2(5) . . . . ? O4B C15B N1B C4B 1.0(9) . . . . ? C16B C15B N1B C4B -176.9(5) . . . . ? O4B C15B N1B Re1B -125.5(6) . . . . ? C16B C15B N1B Re1B 56.6(7) . . . . ? C10B C4B N1B C15B 174.1(5) . . . . ? C5B C4B N1B C15B -74.9(6) . . . . ? C17B C4B N1B C15B 56.5(7) . . . . ? C10B C4B N1B Re1B -51.5(5) . . . . ? C5B C4B N1B Re1B 59.5(5) . . . . ? C17B C4B N1B Re1B -169.2(4) . . . . ? C11B C10B N2B C14B 2.3(9) . . . . ? C4B C10B N2B C14B -179.6(6) . . . . ? C11B C10B N2B Re1B -171.2(5) . . . . ? C4B C10B N2B Re1B 6.9(7) . . . . ? C13B C14B N2B C10B -0.7(10) . . . . ? C13B C14B N2B Re1B 172.0(5) . . . . ? C6B C5B N3B C9B 3.9(11) . . . . ? C4B C5B N3B C9B -177.2(6) . . . . ? C6B C5B N3B Re1B -166.3(6) . . . . ? C4B C5B N3B Re1B 12.6(7) . . . . ? C8B C9B N3B C5B -1.5(11) . . . . ? C8B C9B N3B Re1B 167.9(6) . . . . ? O2B C2B Re1B C1B -48(8) . . . . ? O2B C2B Re1B C3B -137(8) . . . . ? O2B C2B Re1B N2B 58(9) . . . . ? O2B C2B Re1B N1B 124(8) . . . . ? O2B C2B Re1B N3B 50(8) . . . . ? O1B C1B Re1B C2B -26(58) . . . . ? O1B C1B Re1B C3B 64(58) . . . . ? O1B C1B Re1B N2B 162(100) . . . . ? O1B C1B Re1B N1B -165(100) . . . . ? O1B C1B Re1B N3B -117(58) . . . . ? O3B C3B Re1B C2B -72(24) . . . . ? O3B C3B Re1B C1B -159(24) . . . . ? O3B C3B Re1B N2B 106(24) . . . . ? O3B C3B Re1B N1B 31(24) . . . . ? O3B C3B Re1B N3B 33(25) . . . . ? C10B N2B Re1B C2B 39(2) . . . . ? C14B N2B Re1B C2B -133.9(19) . . . . ? C10B N2B Re1B C1B 144.7(5) . . . . ? C14B N2B Re1B C1B -28.3(6) . . . . ? C10B N2B Re1B C3B -125.2(5) . . . . ? C14B N2B Re1B C3B 61.7(6) . . . . ? C10B N2B Re1B N1B -28.5(4) . . . . ? C14B N2B Re1B N1B 158.5(6) . . . . ? C10B N2B Re1B N3B 47.3(5) . . . . ? C14B N2B Re1B N3B -125.7(6) . . . . ? C15B N1B Re1B C2B 1.8(5) . . . . ? C4B N1B Re1B C2B -129.8(4) . . . . ? C15B N1B Re1B C1B 140.3(11) . . . . ? C4B N1B Re1B C1B 8.7(13) . . . . ? C15B N1B Re1B C3B -90.0(5) . . . . ? C4B N1B Re1B C3B 138.5(4) . . . . ? C15B N1B Re1B N2B 174.5(5) . . . . ? C4B N1B Re1B N2B 43.0(4) . . . . ? C15B N1B Re1B N3B 90.3(5) . . . . ? C4B N1B Re1B N3B -41.2(4) . . . . ? C5B N3B Re1B C2B 118.6(5) . . . . ? C9B N3B Re1B C2B -51.2(6) . . . . ? C5B N3B Re1B C1B -154.4(5) . . . . ? C9B N3B Re1B C1B 35.8(6) . . . . ? C5B N3B Re1B C3B 14(2) . . . . ? C9B N3B Re1B C3B -155.7(18) . . . . ? C5B N3B Re1B N2B -60.4(5) . . . . ? C9B N3B Re1B N2B 129.9(6) . . . . ? C5B N3B Re1B N1B 16.2(5) . . . . ? C9B N3B Re1B N1B -153.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 2.966 _refine_diff_density_min -2.303 _refine_diff_density_rms 0.224 # Attachment '- 8b_CCDC821720.cif' data_pd-9-87 _database_code_depnum_ccdc_archive 'CCDC 821720' #TrackingRef '- 8b_CCDC821720.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H18 N3 O4 Re' _chemical_formula_weight 634.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c 21 n' _symmetry_space_group_name_Hall 'P -2n -2ac' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, z+1/2' '-x, y+1/2, -z' 'x+1/2, y+1/2, -z+1/2' _cell_length_a 11.0493(2) _cell_length_b 12.7288(2) _cell_length_c 16.2947(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2291.76(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10888 _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.839 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 5.343 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3372 _exptl_absorpt_correction_T_max 0.5665 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_reflns_number 23097 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5186 _reflns_number_gt 4791 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'DIRDIF08 (Beurskens et al, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.4448P] 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' _refine_ls_abs_structure_Flack 0.023(7) _refine_ls_number_reflns 5186 _refine_ls_number_parameters 292 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0488 _refine_ls_wR_factor_gt 0.0476 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7691(3) 0.4775(3) 0.6672(3) 0.0120(9) Uani 1 1 d . . . C3 C 0.7953(4) 0.4402(3) 0.8269(3) 0.0171(9) Uani 1 1 d . . . C2 C 0.9364(4) 0.5930(3) 0.7481(2) 0.0135(10) Uani 1 1 d . . . C15 C 0.8274(4) 0.7329(3) 0.8865(3) 0.0116(10) Uani 1 1 d . . . C16 C 0.92442(18) 0.67592(19) 0.93432(13) 0.0123(8) Uani 1 1 d G . . C21 C 0.89867(16) 0.58731(19) 0.98102(14) 0.0157(11) Uani 1 1 d G . . H21 H 0.8203 0.5568 0.9790 0.019 Uiso 1 1 calc R . . C20 C 0.9876(2) 0.54339(17) 1.03064(14) 0.0171(10) Uani 1 1 d G . . H20 H 0.9700 0.4828 1.0626 0.021 Uiso 1 1 calc R . . C19 C 1.10231(18) 0.5881(2) 1.03357(14) 0.0227(12) Uani 1 1 d G . . H19 H 1.1631 0.5581 1.0675 0.027 Uiso 1 1 calc R . . C18 C 1.12806(16) 0.6767(2) 0.98687(16) 0.0236(11) Uani 1 1 d G . . H18 H 1.2065 0.7072 0.9889 0.028 Uiso 1 1 calc R . . C17 C 1.0391(2) 0.72062(17) 0.93725(14) 0.0170(9) Uani 1 1 d G . . H17 H 1.0567 0.7812 0.9053 0.020 Uiso 1 1 calc R . . C4 C 0.6225(3) 0.7329(3) 0.8336(2) 0.0086(8) Uani 1 1 d . . . C10 C 0.5257(3) 0.6496(3) 0.8143(2) 0.0096(8) Uani 1 1 d . . . C11 C 0.4025(3) 0.6636(3) 0.8225(2) 0.0145(9) Uani 1 1 d . . . H11 H 0.3712 0.7271 0.8446 0.017 Uiso 1 1 calc R . . C12 C 0.3252(3) 0.5841(4) 0.7981(2) 0.0166(11) Uani 1 1 d . . . H12 H 0.2402 0.5916 0.8048 0.020 Uiso 1 1 calc R . . C13 C 0.3723(4) 0.4940(4) 0.7638(2) 0.0155(9) Uani 1 1 d . . . H13 H 0.3205 0.4388 0.7463 0.019 Uiso 1 1 calc R . . C14 C 0.4963(4) 0.4854(4) 0.7554(2) 0.0132(9) Uani 1 1 d . . . H14 H 0.5286 0.4234 0.7314 0.016 Uiso 1 1 calc R . . C5 C 0.6463(3) 0.7766(3) 0.7473(2) 0.0093(8) Uani 1 1 d . . . C6 C 0.5880(3) 0.8619(3) 0.7126(2) 0.0118(8) Uani 1 1 d . . . H6 H 0.5309 0.9014 0.7435 0.014 Uiso 1 1 calc R . . C7 C 0.6141(4) 0.8889(3) 0.6320(2) 0.0163(9) Uani 1 1 d . . . H7 H 0.5752 0.9474 0.6071 0.020 Uiso 1 1 calc R . . C8 C 0.6977(4) 0.8297(3) 0.5880(2) 0.0146(9) Uani 1 1 d . . . H8 H 0.7201 0.8490 0.5338 0.018 Uiso 1 1 calc R . . C9 C 0.7467(4) 0.7431(4) 0.6248(4) 0.0144(12) Uani 1 1 d . . . H9 H 0.8015 0.7010 0.5941 0.017 Uiso 1 1 calc R . . C22 C 0.5798(2) 0.81079(18) 0.90107(14) 0.0101(8) Uani 1 1 d G . . C27 C 0.5977(2) 0.91862(19) 0.89524(13) 0.0141(9) Uani 1 1 d G . . H27 H 0.6384 0.9472 0.8490 0.017 Uiso 1 1 calc R . . C26 C 0.5560(2) 0.98461(16) 0.95705(15) 0.0181(9) Uani 1 1 d G . . H26 H 0.5682 1.0583 0.9531 0.022 Uiso 1 1 calc R . . C25 C 0.4964(3) 0.9428(2) 1.02470(14) 0.0208(10) Uani 1 1 d G . . H25 H 0.4679 0.9879 1.0669 0.025 Uiso 1 1 calc R . . C24 C 0.4785(3) 0.8349(2) 1.03053(16) 0.0208(12) Uani 1 1 d G . . H24 H 0.4378 0.8063 1.0768 0.025 Uiso 1 1 calc R . . C23 C 0.5202(3) 0.76895(16) 0.96872(19) 0.0117(10) Uani 1 1 d G . . H23 H 0.5079 0.6953 0.9727 0.014 Uiso 1 1 calc R . . N1 N 0.7298(3) 0.6721(3) 0.8625(2) 0.0091(7) Uani 1 1 d . . . N2 N 0.5730(2) 0.5610(5) 0.77963(15) 0.0096(5) Uani 1 1 d . . . N3 N 0.7206(3) 0.7143(3) 0.7030(2) 0.0089(7) Uani 1 1 d . . . O1 O 0.7649(3) 0.4217(3) 0.6115(3) 0.0217(10) Uani 1 1 d . . . O3 O 0.8084(3) 0.3648(3) 0.8647(2) 0.0268(10) Uani 1 1 d . . . O2 O 1.0366(3) 0.6159(2) 0.73636(16) 0.0210(7) Uani 1 1 d . . . O4 O 0.8369(2) 0.8279(2) 0.87300(16) 0.0143(6) Uani 1 1 d . . . Re1 Re 0.768020(10) 0.56515(3) 0.762940(7) 0.00897(5) 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 0.009(2) 0.012(2) 0.015(2) 0.0016(19) 0.0041(15) 0.0032(16) C3 0.014(2) 0.016(2) 0.021(3) -0.008(2) 0.003(2) 0.0005(19) C2 0.020(2) 0.008(3) 0.0121(19) -0.0037(14) -0.0028(15) 0.0033(16) C15 0.013(2) 0.013(2) 0.009(2) -0.0012(19) 0.0056(18) -0.0008(19) C16 0.010(2) 0.017(2) 0.009(2) -0.0027(16) -0.0021(15) 0.0024(17) C21 0.0149(19) 0.019(3) 0.0127(19) -0.0027(15) 0.0025(14) -0.0025(16) C20 0.022(2) 0.015(3) 0.0148(18) 0.0004(17) -0.0017(15) 0.0069(17) C19 0.022(2) 0.027(3) 0.020(2) -0.0049(19) -0.0060(16) 0.0126(19) C18 0.015(2) 0.033(3) 0.023(3) -0.004(2) -0.0062(18) -0.002(2) C17 0.012(2) 0.018(2) 0.022(2) 0.0014(18) -0.0039(17) -0.0039(18) C4 0.0082(19) 0.0062(19) 0.0114(19) 0.0000(15) 0.0001(15) 0.0021(15) C10 0.011(2) 0.0105(19) 0.008(2) 0.0028(16) -0.0003(15) -0.0005(16) C11 0.009(2) 0.016(2) 0.019(2) 0.0028(18) 0.0003(17) 0.0023(16) C12 0.0074(18) 0.024(4) 0.0179(19) 0.0034(19) 0.0010(14) -0.0012(18) C13 0.014(2) 0.022(2) 0.011(2) -0.0015(18) -0.0038(17) -0.008(2) C14 0.017(2) 0.011(2) 0.011(2) 0.0008(16) 0.0029(16) -0.0010(18) C5 0.008(2) 0.008(2) 0.0121(19) -0.0006(15) -0.0012(15) -0.0022(16) C6 0.012(2) 0.010(2) 0.0138(19) -0.0007(17) -0.0031(16) -0.0002(16) C7 0.018(2) 0.016(2) 0.015(2) 0.0050(17) -0.0057(17) -0.0049(17) C8 0.016(2) 0.018(2) 0.010(2) 0.0032(17) -0.0008(17) -0.0046(19) C9 0.017(3) 0.011(3) 0.015(3) -0.005(2) 0.0009(18) -0.0069(19) C22 0.006(2) 0.012(2) 0.012(2) -0.0046(16) -0.0008(15) -0.0006(15) C27 0.015(2) 0.013(2) 0.014(2) -0.0008(17) 0.0015(16) 0.0011(17) C26 0.022(2) 0.012(2) 0.020(2) -0.0059(18) 0.0026(18) 0.0004(18) C25 0.023(2) 0.023(3) 0.017(2) -0.0125(19) 0.0014(18) 0.005(2) C24 0.021(3) 0.027(3) 0.015(3) -0.001(2) 0.003(2) -0.009(2) C23 0.009(3) 0.016(2) 0.010(2) -0.0029(18) 0.001(2) -0.0021(18) N1 0.0117(19) 0.0074(17) 0.0080(19) -0.0007(14) -0.0034(13) 0.0023(13) N2 0.0107(13) 0.0089(15) 0.0093(13) -0.003(3) -0.0004(10) 0.002(3) N3 0.0075(17) 0.0099(17) 0.0093(19) -0.0012(15) -0.0003(12) -0.0004(13) O1 0.022(2) 0.020(2) 0.023(2) -0.012(2) 0.0005(14) 0.0030(15) O3 0.028(2) 0.019(2) 0.033(2) 0.0094(18) 0.0033(18) 0.0092(18) O2 0.0112(17) 0.0257(18) 0.0261(17) -0.0054(13) 0.0029(12) -0.0019(13) O4 0.0092(15) 0.0113(15) 0.0222(16) 0.0024(12) -0.0020(12) -0.0028(12) Re1 0.00766(8) 0.00795(8) 0.01131(8) -0.0009(2) 0.00062(4) 0.0009(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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(6) . ? C1 Re1 1.918(4) . ? C3 O3 1.150(5) . ? C3 Re1 1.925(5) . ? C2 O2 1.160(5) . ? C2 Re1 1.910(4) . ? C15 O4 1.233(5) . ? C15 N1 1.384(6) . ? C15 C16 1.511(5) . ? C16 C21 1.3900 . ? C16 C17 1.3900 . ? C21 C20 1.3900 . ? C21 H21 0.9500 . ? C20 C19 1.3900 . ? C20 H20 0.9500 . ? C19 C18 1.3900 . ? C19 H19 0.9500 . ? C18 C17 1.3900 . ? C18 H18 0.9500 . ? C17 H17 0.9500 . ? C4 N1 1.492(5) . ? C4 C5 1.535(5) . ? C4 C10 1.539(5) . ? C4 C22 1.554(4) . ? C10 N2 1.365(6) . ? C10 C11 1.380(5) . ? C11 C12 1.383(6) . ? C11 H11 0.9500 . ? C12 C13 1.378(6) . ? C12 H12 0.9500 . ? C13 C14 1.381(6) . ? C13 H13 0.9500 . ? C14 N2 1.342(6) . ? C14 H14 0.9500 . ? C5 N3 1.350(5) . ? C5 C6 1.384(5) . ? C6 C7 1.388(5) . ? C6 H6 0.9500 . ? C7 C8 1.391(6) . ? C7 H7 0.9500 . ? C8 C9 1.367(7) . ? C8 H8 0.9500 . ? C9 N3 1.358(7) . ? C9 H9 0.9500 . ? C22 C27 1.3900 . ? C22 C23 1.3900 . ? C27 C26 1.3900 . ? C27 H27 0.9500 . ? C26 C25 1.3900 . ? C26 H26 0.9500 . ? C25 C24 1.3900 . ? C25 H25 0.9500 . ? C24 C23 1.3900 . ? C24 H24 0.9500 . ? C23 H23 0.9500 . ? N1 Re1 2.159(3) . ? N2 Re1 2.173(2) . ? N3 Re1 2.198(3) . ? 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 176.4(4) . . ? O3 C3 Re1 178.1(4) . . ? O2 C2 Re1 175.5(3) . . ? O4 C15 N1 124.4(4) . . ? O4 C15 C16 120.1(4) . . ? N1 C15 C16 115.4(3) . . ? C21 C16 C17 120.0 . . ? C21 C16 C15 121.8(2) . . ? C17 C16 C15 117.9(2) . . ? C16 C21 C20 120.0 . . ? C16 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C19 C20 C21 120.0 . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C18 C19 C20 120.0 . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C17 C16 120.0 . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? N1 C4 C5 109.9(3) . . ? N1 C4 C10 105.0(3) . . ? C5 C4 C10 100.5(3) . . ? N1 C4 C22 110.5(3) . . ? C5 C4 C22 118.0(3) . . ? C10 C4 C22 111.9(3) . . ? N2 C10 C11 121.7(3) . . ? N2 C10 C4 112.8(3) . . ? C11 C10 C4 125.2(3) . . ? C10 C11 C12 119.1(4) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 119.5(4) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 118.7(4) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? N2 C14 C13 122.8(4) . . ? N2 C14 H14 118.6 . . ? C13 C14 H14 118.6 . . ? N3 C5 C6 121.7(3) . . ? N3 C5 C4 112.4(3) . . ? C6 C5 C4 125.4(3) . . ? C5 C6 C7 119.0(4) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C6 C7 C8 119.4(4) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C7 118.4(4) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? N3 C9 C8 123.0(4) . . ? N3 C9 H9 118.5 . . ? C8 C9 H9 118.5 . . ? C27 C22 C23 120.0 . . ? C27 C22 C4 122.6(2) . . ? C23 C22 C4 117.4(2) . . ? C26 C27 C22 120.0 . . ? C26 C27 H27 120.0 . . ? C22 C27 H27 120.0 . . ? C27 C26 C25 120.0 . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C24 C25 C26 120.0 . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C23 C24 C25 120.0 . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C23 C22 120.0 . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C15 N1 C4 114.7(3) . . ? C15 N1 Re1 114.4(3) . . ? C4 N1 Re1 104.2(2) . . ? C14 N2 C10 118.2(3) . . ? C14 N2 Re1 127.4(3) . . ? C10 N2 Re1 114.3(3) . . ? C5 N3 C9 118.2(4) . . ? C5 N3 Re1 114.5(2) . . ? C9 N3 Re1 126.8(3) . . ? C2 Re1 C1 89.95(15) . . ? C2 Re1 C3 93.98(17) . . ? C1 Re1 C3 87.62(18) . . ? C2 Re1 N1 99.70(14) . . ? C1 Re1 N1 168.23(13) . . ? C3 Re1 N1 98.33(16) . . ? C2 Re1 N2 170.68(19) . . ? C1 Re1 N2 95.38(15) . . ? C3 Re1 N2 93.88(19) . . ? N1 Re1 N2 74.18(14) . . ? C2 Re1 N3 90.89(14) . . ? C1 Re1 N3 98.21(16) . . ? C3 Re1 N3 172.41(16) . . ? N1 Re1 N3 75.08(12) . . ? N2 Re1 N3 80.80(16) . . ? 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 O4 C15 C16 C21 151.5(3) . . . . ? N1 C15 C16 C21 -26.8(5) . . . . ? O4 C15 C16 C17 -22.1(5) . . . . ? N1 C15 C16 C17 159.6(3) . . . . ? C17 C16 C21 C20 0.0 . . . . ? C15 C16 C21 C20 -173.5(3) . . . . ? C16 C21 C20 C19 0.0 . . . . ? C21 C20 C19 C18 0.0 . . . . ? C20 C19 C18 C17 0.0 . . . . ? C19 C18 C17 C16 0.0 . . . . ? C21 C16 C17 C18 0.0 . . . . ? C15 C16 C17 C18 173.7(3) . . . . ? N1 C4 C10 N2 -37.9(4) . . . . ? C5 C4 C10 N2 76.2(4) . . . . ? C22 C4 C10 N2 -157.7(3) . . . . ? N1 C4 C10 C11 148.3(4) . . . . ? C5 C4 C10 C11 -97.6(4) . . . . ? C22 C4 C10 C11 28.4(5) . . . . ? N2 C10 C11 C12 2.7(6) . . . . ? C4 C10 C11 C12 176.0(4) . . . . ? C10 C11 C12 C13 -2.0(6) . . . . ? C11 C12 C13 C14 0.5(6) . . . . ? C12 C13 C14 N2 0.4(6) . . . . ? N1 C4 C5 N3 30.5(4) . . . . ? C10 C4 C5 N3 -79.8(4) . . . . ? C22 C4 C5 N3 158.3(3) . . . . ? N1 C4 C5 C6 -157.7(4) . . . . ? C10 C4 C5 C6 92.0(4) . . . . ? C22 C4 C5 C6 -29.9(5) . . . . ? N3 C5 C6 C7 -5.2(6) . . . . ? C4 C5 C6 C7 -176.3(4) . . . . ? C5 C6 C7 C8 0.2(6) . . . . ? C6 C7 C8 C9 3.4(6) . . . . ? C7 C8 C9 N3 -2.3(7) . . . . ? N1 C4 C22 C27 107.1(3) . . . . ? C5 C4 C22 C27 -20.4(4) . . . . ? C10 C4 C22 C27 -136.2(3) . . . . ? N1 C4 C22 C23 -73.7(3) . . . . ? C5 C4 C22 C23 158.8(3) . . . . ? C10 C4 C22 C23 42.9(3) . . . . ? C23 C22 C27 C26 0.0 . . . . ? C4 C22 C27 C26 179.1(3) . . . . ? C22 C27 C26 C25 0.0 . . . . ? C27 C26 C25 C24 0.0 . . . . ? C26 C25 C24 C23 0.0 . . . . ? C25 C24 C23 C22 0.0 . . . . ? C27 C22 C23 C24 0.0 . . . . ? C4 C22 C23 C24 -179.2(2) . . . . ? O4 C15 N1 C4 -12.2(6) . . . . ? C16 C15 N1 C4 166.0(3) . . . . ? O4 C15 N1 Re1 108.1(4) . . . . ? C16 C15 N1 Re1 -73.7(4) . . . . ? C5 C4 N1 C15 75.1(4) . . . . ? C10 C4 N1 C15 -177.7(3) . . . . ? C22 C4 N1 C15 -56.8(4) . . . . ? C5 C4 N1 Re1 -50.7(3) . . . . ? C10 C4 N1 Re1 56.5(3) . . . . ? C22 C4 N1 Re1 177.4(2) . . . . ? C13 C14 N2 C10 0.3(6) . . . . ? C13 C14 N2 Re1 -175.2(3) . . . . ? C11 C10 N2 C14 -1.8(6) . . . . ? C4 C10 N2 C14 -175.9(3) . . . . ? C11 C10 N2 Re1 174.2(3) . . . . ? C4 C10 N2 Re1 0.1(4) . . . . ? C6 C5 N3 C9 6.4(6) . . . . ? C4 C5 N3 C9 178.5(4) . . . . ? C6 C5 N3 Re1 -166.4(3) . . . . ? C4 C5 N3 Re1 5.8(4) . . . . ? C8 C9 N3 C5 -2.5(7) . . . . ? C8 C9 N3 Re1 169.2(3) . . . . ? O2 C2 Re1 C1 95(4) . . . . ? O2 C2 Re1 C3 -178(100) . . . . ? O2 C2 Re1 N1 -78(4) . . . . ? O2 C2 Re1 N2 -30(5) . . . . ? O2 C2 Re1 N3 -3(4) . . . . ? O1 C1 Re1 C2 150(6) . . . . ? O1 C1 Re1 C3 56(6) . . . . ? O1 C1 Re1 N1 -65(6) . . . . ? O1 C1 Re1 N2 -38(6) . . . . ? O1 C1 Re1 N3 -119(6) . . . . ? O3 C3 Re1 C2 -163(13) . . . . ? O3 C3 Re1 C1 -74(13) . . . . ? O3 C3 Re1 N1 96(13) . . . . ? O3 C3 Re1 N2 22(13) . . . . ? O3 C3 Re1 N3 67(13) . . . . ? C15 N1 Re1 C2 2.6(3) . . . . ? C4 N1 Re1 C2 128.6(2) . . . . ? C15 N1 Re1 C1 -142.1(7) . . . . ? C4 N1 Re1 C1 -16.0(9) . . . . ? C15 N1 Re1 C3 98.2(3) . . . . ? C4 N1 Re1 C3 -135.8(2) . . . . ? C15 N1 Re1 N2 -170.2(3) . . . . ? C4 N1 Re1 N2 -44.1(2) . . . . ? C15 N1 Re1 N3 -85.7(3) . . . . ? C4 N1 Re1 N3 40.3(2) . . . . ? C14 N2 Re1 C2 150.9(8) . . . . ? C10 N2 Re1 C2 -24.7(8) . . . . ? C14 N2 Re1 C1 26.2(4) . . . . ? C10 N2 Re1 C1 -149.4(3) . . . . ? C14 N2 Re1 C3 -61.8(4) . . . . ? C10 N2 Re1 C3 122.7(3) . . . . ? C14 N2 Re1 N1 -159.3(4) . . . . ? C10 N2 Re1 N1 25.1(3) . . . . ? C14 N2 Re1 N3 123.7(3) . . . . ? C10 N2 Re1 N3 -51.9(3) . . . . ? C5 N3 Re1 C2 -126.7(3) . . . . ? C9 N3 Re1 C2 61.3(4) . . . . ? C5 N3 Re1 C1 143.2(3) . . . . ? C9 N3 Re1 C1 -28.8(4) . . . . ? C5 N3 Re1 C3 3.2(12) . . . . ? C9 N3 Re1 C3 -168.8(10) . . . . ? C5 N3 Re1 N1 -26.9(3) . . . . ? C9 N3 Re1 N1 161.1(4) . . . . ? C5 N3 Re1 N2 49.0(3) . . . . ? C9 N3 Re1 N2 -123.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.716 _refine_diff_density_min -1.159 _refine_diff_density_rms 0.116 # Attachment '- 9c_CCDC821721.cif' data_ykc5p1 _database_code_depnum_ccdc_archive 'CCDC 821721' #TrackingRef '- 9c_CCDC821721.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 N3 O4 Re, Br' _chemical_formula_sum 'C16 H13 Br N3 O4 Re' _chemical_formula_weight 577.40 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 orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 12.2711(4) _cell_length_b 10.3063(3) _cell_length_c 14.6466(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1852.35(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 50257 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 8.742 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3021 _exptl_absorpt_correction_T_max 0.7794 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 21095 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2242 _reflns_number_gt 2018 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'DIRDIF08 (Beurskens et al, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0115P)^2^+5.6568P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2242 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0521 _refine_ls_wR_factor_gt 0.0492 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _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 C1 C 0.4468(5) 0.7500 0.2199(4) 0.0406(15) Uani 1 2 d S . . C2 C 0.5573(3) 0.8798(4) 0.3542(2) 0.0308(9) Uani 1 1 d . . . C4 C 0.2956(4) 0.7500 0.5045(3) 0.0184(9) Uani 1 2 d S . . H4 H 0.2702 0.7500 0.5694 0.022 Uiso 1 2 calc SR . . C5 C 0.2558(3) 0.8682(3) 0.4518(2) 0.0210(7) Uani 1 1 d . . . C6 C 0.1703(3) 0.9464(4) 0.4783(3) 0.0269(8) Uani 1 1 d . . . H6 H 0.1348 0.9333 0.5352 0.032 Uiso 1 1 calc R . . C7 C 0.1376(3) 1.0447(4) 0.4197(3) 0.0325(9) Uani 1 1 d . . . H7 H 0.0785 1.0999 0.4354 0.039 Uiso 1 1 calc R . . C8 C 0.1922(3) 1.0611(4) 0.3379(3) 0.0342(9) Uani 1 1 d . . . H8 H 0.1700 1.1269 0.2965 0.041 Uiso 1 1 calc R . . C9 C 0.2784(3) 0.9822(4) 0.3169(3) 0.0291(8) Uani 1 1 d . . . H9 H 0.3167 0.9959 0.2613 0.035 Uiso 1 1 calc R . . C15 C 0.4740(4) 0.7500 0.5698(3) 0.0195(10) Uani 1 2 d S . . C16 C 0.5953(4) 0.7500 0.5631(4) 0.0320(12) Uani 1 2 d S . . H16A H 0.6268 0.7500 0.6246 0.048 Uiso 1 2 calc SR . . H16B H 0.6194 0.8276 0.5302 0.048 Uiso 0.50 1 calc PR . . H16C H 0.6194 0.6724 0.5302 0.048 Uiso 0.50 1 calc PR . . N1 N 0.4149(3) 0.7500 0.4971(2) 0.0167(8) Uani 1 2 d S . . N3 N 0.3104(2) 0.8862(3) 0.37256(19) 0.0224(6) Uani 1 1 d . . . O1 O 0.4466(5) 0.7500 0.1420(3) 0.0638(16) Uani 1 2 d S . . O2 O 0.6251(3) 0.9573(3) 0.3601(2) 0.0449(8) Uani 1 1 d . . . O3 O 0.4281(3) 0.7500 0.6507(2) 0.0262(8) Uani 1 2 d S . . Br1 Br 0.58333(4) 0.7500 0.81511(3) 0.02418(12) Uani 1 2 d S . . Re1 Re 0.445775(17) 0.7500 0.352483(13) 0.02346(7) Uani 1 2 d S . . H3A H 0.475(5) 0.7500 0.690(4) 0.035 Uiso 1 2 d S . . 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 0.047(4) 0.050(4) 0.025(3) 0.000 0.006(3) 0.000 C2 0.034(2) 0.037(2) 0.0218(19) 0.0042(16) 0.0088(16) -0.0008(18) C4 0.015(2) 0.023(2) 0.017(2) 0.000 -0.0056(18) 0.000 C5 0.0215(17) 0.0236(18) 0.0180(16) -0.0011(14) -0.0035(13) -0.0016(14) C6 0.0215(18) 0.0269(19) 0.0321(19) -0.0009(16) -0.0015(15) -0.0009(14) C7 0.0235(19) 0.026(2) 0.048(2) 0.0010(17) -0.0047(16) 0.0032(15) C8 0.034(2) 0.030(2) 0.039(2) 0.0099(17) -0.0180(18) -0.0036(17) C9 0.034(2) 0.028(2) 0.0255(18) 0.0042(16) -0.0088(16) -0.0047(16) C15 0.025(3) 0.016(2) 0.017(2) 0.000 0.0053(19) 0.000 C16 0.024(3) 0.051(4) 0.022(3) 0.000 -0.001(2) 0.000 N1 0.018(2) 0.021(2) 0.0112(19) 0.000 -0.0008(15) 0.000 N3 0.0258(15) 0.0218(15) 0.0197(14) 0.0017(12) -0.0062(12) -0.0029(12) O1 0.086(4) 0.093(4) 0.013(2) 0.000 0.002(2) 0.000 O2 0.0440(18) 0.0513(19) 0.0395(17) 0.0094(15) 0.0050(14) -0.0165(16) O3 0.0205(19) 0.045(2) 0.0134(17) 0.000 -0.0036(14) 0.000 Br1 0.0224(2) 0.0338(3) 0.0164(2) 0.000 -0.00276(18) 0.000 Re1 0.02671(12) 0.02965(12) 0.01402(10) 0.000 0.00298(8) 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.140(7) . ? C1 Re1 1.942(6) . ? C2 O2 1.157(5) . ? C2 Re1 1.914(4) . ? C4 N1 1.468(6) . ? C4 C5 1.522(4) 7_575 ? C4 C5 1.522(4) . ? C4 H4 1.0000 . ? C5 N3 1.353(4) . ? C5 C6 1.379(5) . ? C6 C7 1.388(5) . ? C6 H6 0.9500 . ? C7 C8 1.382(6) . ? C7 H7 0.9500 . ? C8 C9 1.370(6) . ? C8 H8 0.9500 . ? C9 N3 1.341(5) . ? C9 H9 0.9500 . ? C15 N1 1.288(6) . ? C15 O3 1.312(6) . ? C15 C16 1.492(7) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 Re1 2.151(4) . ? N3 Re1 2.195(3) . ? O3 H3A 0.81(6) . ? Re1 C2 1.914(4) 7_575 ? Re1 N3 2.195(3) 7_575 ? 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 179.5(6) . . ? O2 C2 Re1 176.4(3) . . ? N1 C4 C5 106.4(3) . 7_575 ? N1 C4 C5 106.4(3) . . ? C5 C4 C5 106.3(4) 7_575 . ? N1 C4 H4 112.4 . . ? C5 C4 H4 112.4 7_575 . ? C5 C4 H4 112.4 . . ? N3 C5 C6 122.5(3) . . ? N3 C5 C4 112.7(3) . . ? C6 C5 C4 124.7(3) . . ? C5 C6 C7 118.3(4) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C8 C7 C6 119.0(4) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 C7 119.8(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? N3 C9 C8 121.8(4) . . ? N3 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? N1 C15 O3 120.3(4) . . ? N1 C15 C16 120.5(4) . . ? O3 C15 C16 119.2(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 N1 C4 120.0(4) . . ? C15 N1 Re1 135.6(3) . . ? C4 N1 Re1 104.4(3) . . ? C9 N3 C5 118.6(3) . . ? C9 N3 Re1 127.7(3) . . ? C5 N3 Re1 113.7(2) . . ? C15 O3 H3A 109(5) . . ? C2 Re1 C2 88.7(2) . 7_575 ? C2 Re1 C1 90.50(18) . . ? C2 Re1 C1 90.50(18) 7_575 . ? C2 Re1 N1 96.48(13) . . ? C2 Re1 N1 96.48(13) 7_575 . ? C1 Re1 N1 170.2(2) . . ? C2 Re1 N3 170.58(13) . 7_575 ? C2 Re1 N3 95.31(15) 7_575 7_575 ? C1 Re1 N3 97.97(16) . 7_575 ? N1 Re1 N3 74.63(10) . 7_575 ? C2 Re1 N3 95.31(14) . . ? C2 Re1 N3 170.58(13) 7_575 . ? C1 Re1 N3 97.97(16) . . ? N1 Re1 N3 74.63(10) . . ? N3 Re1 N3 79.51(15) 7_575 . ? 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 C4 C5 N3 41.2(4) . . . . ? C5 C4 C5 N3 -71.9(4) 7_575 . . . ? N1 C4 C5 C6 -141.7(3) . . . . ? C5 C4 C5 C6 105.2(4) 7_575 . . . ? N3 C5 C6 C7 1.9(5) . . . . ? C4 C5 C6 C7 -174.9(3) . . . . ? C5 C6 C7 C8 -0.6(5) . . . . ? C6 C7 C8 C9 -1.2(6) . . . . ? C7 C8 C9 N3 1.7(6) . . . . ? O3 C15 N1 C4 0.000(1) . . . . ? C16 C15 N1 C4 180.0 . . . . ? O3 C15 N1 Re1 180.0 . . . . ? C16 C15 N1 Re1 0.000(1) . . . . ? C5 C4 N1 C15 -123.5(2) 7_575 . . . ? C5 C4 N1 C15 123.5(2) . . . . ? C5 C4 N1 Re1 56.5(2) 7_575 . . . ? C5 C4 N1 Re1 -56.5(2) . . . . ? C8 C9 N3 C5 -0.5(5) . . . . ? C8 C9 N3 Re1 -179.7(3) . . . . ? C6 C5 N3 C9 -1.4(5) . . . . ? C4 C5 N3 C9 175.8(3) . . . . ? C6 C5 N3 Re1 178.0(3) . . . . ? C4 C5 N3 Re1 -4.9(3) . . . . ? O2 C2 Re1 C2 -81(6) . . . 7_575 ? O2 C2 Re1 C1 -171(6) . . . . ? O2 C2 Re1 N1 16(6) . . . . ? O2 C2 Re1 N3 35(6) . . . 7_575 ? O2 C2 Re1 N3 91(6) . . . . ? O1 C1 Re1 C2 -135.66(14) . . . . ? O1 C1 Re1 C2 135.65(14) . . . 7_575 ? O1 C1 Re1 N1 0.00(5) . . . . ? O1 C1 Re1 N3 40.22(10) . . . 7_575 ? O1 C1 Re1 N3 -40.22(9) . . . . ? C15 N1 Re1 C2 -44.70(12) . . . . ? C4 N1 Re1 C2 135.30(12) . . . . ? C15 N1 Re1 C2 44.70(12) . . . 7_575 ? C4 N1 Re1 C2 -135.30(12) . . . 7_575 ? C15 N1 Re1 C1 180.000(2) . . . . ? C4 N1 Re1 C1 0.000(2) . . . . ? C15 N1 Re1 N3 138.45(8) . . . 7_575 ? C4 N1 Re1 N3 -41.55(8) . . . 7_575 ? C15 N1 Re1 N3 -138.45(8) . . . . ? C4 N1 Re1 N3 41.55(8) . . . . ? C9 N3 Re1 C2 63.2(3) . . . . ? C5 N3 Re1 C2 -116.1(2) . . . . ? C9 N3 Re1 C2 178.0(8) . . . 7_575 ? C5 N3 Re1 C2 -1.3(10) . . . 7_575 ? C9 N3 Re1 C1 -28.1(3) . . . . ? C5 N3 Re1 C1 152.6(3) . . . . ? C9 N3 Re1 N1 158.5(3) . . . . ? C5 N3 Re1 N1 -20.8(2) . . . . ? C9 N3 Re1 N3 -124.8(3) . . . 7_575 ? C5 N3 Re1 N3 55.9(3) . . . 7_575 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A Br1 0.81(6) 2.26(7) 3.070(4) 171(6) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.317 _refine_diff_density_min -1.033 _refine_diff_density_rms 0.127