# 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 ? loop_ _publ_author_name H.Qayyum R.S.Herrick C.J.Ziegler _publ_contact_author_name 'Christopher J. Ziegler' _publ_contact_author_email ziegler@uakron.edu data_1 _database_code_depnum_ccdc_archive 'CCDC 810590' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 N4 O11 Re2 ' _chemical_formula_weight 884.79 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.275(4) _cell_length_b 10.629(4) _cell_length_c 21.731(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.135(6) _cell_angle_gamma 90.00 _cell_volume 2546.0(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2332 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 22.05 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 9.568 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2170 _exptl_absorpt_correction_T_max 0.9104 _exptl_absorpt_process_details ; SADABS Sheldrick, 2004 [Sheldrick, G. M. (2004)] ; _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.080071 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20394 _diffrn_reflns_av_R_equivalents 0.1081 _diffrn_reflns_av_sigmaI/netI 0.1132 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.25 _reflns_number_total 5631 _reflns_number_gt 3782 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms were assigned ideal positions and refined isotropically as riding atoms. Hydrogen atoms were not modeled on the water solvent molecule. ; _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^)+(0.0905P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5631 _refine_ls_number_parameters 352 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1700 _refine_ls_wR_factor_gt 0.1544 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.969 _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 0.6263(14) 0.1897(14) 0.0728(7) 0.038(4) Uani 1 1 d . . . C2 C 0.3878(13) 0.1545(14) 0.0343(8) 0.034(3) Uani 1 1 d . . . C3 C 0.5130(13) 0.0111(17) 0.1192(7) 0.040(4) Uani 1 1 d . . . C4 C 0.5146(12) 0.4758(13) 0.0877(6) 0.029(3) Uani 1 1 d . . . H4 H 0.5780 0.4540 0.0669 0.035 Uiso 1 1 calc R . . C5 C 0.4831(11) 0.6020(13) 0.0900(7) 0.028(3) Uani 1 1 d . . . H5 H 0.5236 0.6638 0.0705 0.033 Uiso 1 1 calc R . . C6 C 0.3957(13) 0.6361(15) 0.1199(7) 0.036(3) Uani 1 1 d . . . H6 H 0.3742 0.7223 0.1217 0.043 Uiso 1 1 calc R . . C7 C 0.3376(13) 0.5469(12) 0.1478(7) 0.032(3) Uani 1 1 d . . . H7 H 0.2752 0.5710 0.1687 0.039 Uiso 1 1 calc R . . C8 C 0.3695(11) 0.4208(12) 0.1457(6) 0.024(3) Uani 1 1 d . . . C9 C 0.3154(11) 0.3199(13) 0.1743(6) 0.026(3) Uani 1 1 d . . . H9 H 0.2576 0.3371 0.1993 0.031 Uiso 1 1 calc R . . C10 C 0.2948(11) 0.0978(13) 0.1930(7) 0.029(3) Uani 1 1 d . . . H10A H 0.2798 0.0271 0.1626 0.035 Uiso 1 1 calc R . . H10B H 0.2164 0.1227 0.2030 0.035 Uiso 1 1 calc R . . C11 C 0.3859(11) 0.0547(15) 0.2552(6) 0.028(3) Uani 1 1 d . . . C12 C 0.6436(15) -0.0248(16) 0.3416(7) 0.042(4) Uani 1 1 d U . . C13 C 0.4845(14) -0.0254(15) 0.4107(7) 0.037(3) Uani 1 1 d . . . C14 C 0.6950(13) 0.0925(13) 0.4485(8) 0.036(4) Uani 1 1 d . . . C15 C 0.4059(13) 0.2928(15) 0.4385(7) 0.035(4) Uani 1 1 d . . . H15 H 0.3732 0.2193 0.4534 0.042 Uiso 1 1 calc R . . C16 C 0.3621(14) 0.4115(16) 0.4524(7) 0.041(4) Uani 1 1 d . . . H16 H 0.3013 0.4168 0.4766 0.049 Uiso 1 1 calc R . . C17 C 0.4067(13) 0.5190(16) 0.4311(7) 0.041(4) Uani 1 1 d . . . H17 H 0.3783 0.5998 0.4400 0.049 Uiso 1 1 calc R . . C18 C 0.4985(14) 0.5045(14) 0.3947(7) 0.039(4) Uani 1 1 d . . . H18 H 0.5327 0.5770 0.3796 0.047 Uiso 1 1 calc R . . C19 C 0.5360(13) 0.3917(14) 0.3818(6) 0.031(3) Uani 1 1 d . . . C20 C 0.6294(13) 0.3731(15) 0.3431(7) 0.037(4) Uani 1 1 d . . . H20 H 0.6649 0.4417 0.3255 0.044 Uiso 1 1 calc R . . C21 C 0.7510(12) 0.2365(17) 0.2980(7) 0.041(4) Uani 1 1 d . . . H21A H 0.8120 0.1768 0.3209 0.049 Uiso 1 1 calc R . . H21B H 0.7930 0.3169 0.2938 0.049 Uiso 1 1 calc R . . C22 C 0.6999(12) 0.1840(14) 0.2321(7) 0.032(3) Uani 1 1 d . . . N1 N 0.4593(9) 0.3828(10) 0.1134(5) 0.021(2) Uani 1 1 d . . . N2 N 0.3470(9) 0.2039(10) 0.1652(5) 0.022(2) Uani 1 1 d . . . N3 N 0.4951(10) 0.2802(11) 0.4037(6) 0.031(3) Uani 1 1 d . . . N4 N 0.6587(10) 0.2584(13) 0.3353(5) 0.036(3) Uani 1 1 d . . . O1 O 0.7100(10) 0.2022(11) 0.0481(6) 0.051(3) Uani 1 1 d . . . O2 O 0.3203(11) 0.1320(11) -0.0134(5) 0.046(3) Uani 1 1 d . . . O3 O 0.5268(10) -0.1031(9) 0.1220(5) 0.041(3) Uani 1 1 d . . . O4 O 0.6983(10) -0.1082(11) 0.3214(6) 0.049(3) Uani 1 1 d . . . O5 O 0.4363(10) -0.1030(11) 0.4328(6) 0.052(3) Uani 1 1 d . . . O6 O 0.7728(9) 0.0769(10) 0.4934(5) 0.040(3) Uani 1 1 d . . . O7 O 0.4295(9) 0.1384(9) 0.2924(5) 0.032(2) Uani 1 1 d . . . O8 O 0.3986(9) -0.0631(10) 0.2603(5) 0.041(3) Uani 1 1 d . . . O9 O 0.5943(8) 0.2248(9) 0.2057(4) 0.027(2) Uani 1 1 d . . . O10 O 0.7622(9) 0.1146(9) 0.2065(5) 0.040(3) Uani 1 1 d . . . O11 O 0.4820(10) 0.6890(10) 0.2765(6) 0.049(3) Uani 1 1 d . . . Re1 Re 0.49294(5) 0.18363(5) 0.11380(3) 0.02424(17) Uani 1 1 d . . . Re2 Re 0.57011(5) 0.10680(6) 0.37543(3) 0.03009(19) 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 0.032(8) 0.036(8) 0.046(10) -0.007(7) 0.008(7) 0.001(7) C2 0.031(8) 0.033(8) 0.044(10) 0.007(7) 0.019(7) 0.010(7) C3 0.034(8) 0.064(11) 0.023(8) -0.008(7) 0.009(6) -0.006(8) C4 0.019(6) 0.035(8) 0.028(7) 0.014(6) -0.003(5) -0.008(6) C5 0.018(6) 0.031(7) 0.030(7) -0.014(6) -0.003(5) -0.004(6) C6 0.025(7) 0.038(8) 0.046(9) 0.001(7) 0.013(7) 0.002(7) C7 0.031(7) 0.021(7) 0.048(9) -0.015(7) 0.015(7) -0.005(6) C8 0.015(6) 0.029(7) 0.029(7) -0.001(6) 0.011(5) 0.002(5) C9 0.019(6) 0.037(8) 0.019(7) -0.002(6) 0.003(5) 0.001(6) C10 0.015(6) 0.038(8) 0.033(8) 0.000(6) 0.001(5) -0.009(6) C11 0.010(6) 0.050(9) 0.024(7) 0.016(7) 0.005(5) 0.004(6) C12 0.039(7) 0.045(7) 0.040(7) 0.009(6) 0.004(6) -0.014(6) C13 0.040(9) 0.037(8) 0.032(8) -0.006(7) 0.005(7) 0.009(7) C14 0.027(8) 0.032(8) 0.050(10) 0.000(7) 0.010(7) -0.004(6) C15 0.028(7) 0.047(10) 0.033(8) 0.001(7) 0.012(6) 0.001(7) C16 0.033(8) 0.063(11) 0.024(8) -0.001(7) 0.004(6) 0.021(8) C17 0.033(8) 0.042(9) 0.046(10) 0.005(8) 0.006(7) 0.005(7) C18 0.035(8) 0.035(8) 0.043(10) 0.004(7) 0.002(7) 0.001(7) C19 0.030(7) 0.037(8) 0.023(7) -0.010(6) -0.001(6) -0.007(7) C20 0.031(8) 0.047(10) 0.032(8) 0.000(7) 0.003(7) 0.000(7) C21 0.019(7) 0.073(11) 0.029(8) -0.004(8) 0.002(6) 0.002(8) C22 0.021(7) 0.040(8) 0.030(8) 0.007(7) -0.006(6) -0.009(7) N1 0.010(5) 0.033(6) 0.019(5) 0.013(5) 0.002(4) 0.003(4) N2 0.013(5) 0.034(6) 0.020(6) 0.008(5) 0.001(4) 0.000(5) N3 0.022(6) 0.033(6) 0.036(7) 0.006(5) 0.003(5) 0.003(5) N4 0.019(6) 0.054(8) 0.033(7) 0.006(6) 0.001(5) -0.005(6) O1 0.043(7) 0.065(8) 0.057(8) -0.005(6) 0.035(6) -0.006(6) O2 0.052(7) 0.059(7) 0.027(6) 0.008(5) 0.006(5) -0.007(6) O3 0.041(6) 0.027(6) 0.053(7) -0.004(5) 0.009(5) -0.001(5) O4 0.042(7) 0.053(7) 0.051(7) 0.000(6) 0.008(6) 0.007(6) O5 0.032(6) 0.063(8) 0.063(8) 0.024(6) 0.016(6) -0.001(6) O6 0.024(5) 0.068(8) 0.026(6) 0.004(5) -0.001(4) 0.001(5) O7 0.028(5) 0.033(5) 0.033(6) 0.004(5) 0.001(4) -0.011(4) O8 0.031(6) 0.044(7) 0.045(7) 0.006(5) 0.000(5) -0.003(5) O9 0.022(5) 0.040(5) 0.022(5) 0.006(4) 0.010(4) 0.001(4) O10 0.029(6) 0.041(6) 0.050(7) -0.003(5) 0.007(5) 0.008(5) O11 0.040(6) 0.050(7) 0.062(8) 0.010(6) 0.017(6) -0.006(5) Re1 0.0188(3) 0.0280(3) 0.0271(3) 0.0012(2) 0.0076(2) 0.0004(2) Re2 0.0201(3) 0.0433(4) 0.0269(3) 0.0048(3) 0.0051(2) 0.0006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.186(18) . ? C1 Re1 1.904(16) . ? C2 O2 1.174(18) . ? C2 Re1 1.904(17) . ? C3 O3 1.225(19) . ? C3 Re1 1.848(18) . ? C4 N1 1.351(16) . ? C4 C5 1.390(19) . ? C5 C6 1.339(19) . ? C6 C7 1.36(2) . ? C7 C8 1.391(17) . ? C8 N1 1.407(16) . ? C8 C9 1.437(18) . ? C9 N2 1.309(16) . ? C10 N2 1.459(16) . ? C10 C11 1.584(17) . ? C11 O7 1.233(17) . ? C11 O8 1.262(17) . ? C12 O4 1.21(2) . ? C12 Re2 1.854(19) . ? C13 O5 1.148(18) . ? C13 Re2 1.950(18) . ? C14 O6 1.179(18) . ? C14 Re2 1.894(16) . ? C15 N3 1.386(18) . ? C15 C16 1.41(2) . ? C16 C17 1.37(2) . ? C17 C18 1.44(2) . ? C18 C19 1.32(2) . ? C19 N3 1.390(19) . ? C19 C20 1.49(2) . ? C20 N4 1.284(19) . ? C21 N4 1.466(18) . ? C21 C22 1.532(19) . ? C22 O10 1.229(18) . ? C22 O9 1.284(16) . ? N1 Re1 2.151(11) . ? N2 Re1 2.186(10) . ? N3 Re2 2.170(12) . ? N4 Re2 2.173(12) . ? O7 Re2 2.164(9) . ? O9 Re1 2.127(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 Re1 175.5(13) . . ? O2 C2 Re1 176.7(13) . . ? O3 C3 Re1 179.2(13) . . ? N1 C4 C5 123.1(14) . . ? C6 C5 C4 119.9(14) . . ? C5 C6 C7 119.8(14) . . ? C6 C7 C8 120.3(13) . . ? C7 C8 N1 120.7(12) . . ? C7 C8 C9 124.7(12) . . ? N1 C8 C9 114.6(11) . . ? N2 C9 C8 119.0(12) . . ? N2 C10 C11 109.3(10) . . ? O7 C11 O8 129.5(12) . . ? O7 C11 C10 116.6(13) . . ? O8 C11 C10 113.8(13) . . ? O4 C12 Re2 176.1(14) . . ? O5 C13 Re2 178.4(14) . . ? O6 C14 Re2 176.5(13) . . ? N3 C15 C16 122.0(14) . . ? C17 C16 C15 120.3(15) . . ? C16 C17 C18 117.1(15) . . ? C19 C18 C17 120.9(15) . . ? C18 C19 N3 123.9(15) . . ? C18 C19 C20 122.3(15) . . ? N3 C19 C20 113.8(13) . . ? N4 C20 C19 115.6(14) . . ? N4 C21 C22 113.8(11) . . ? O10 C22 O9 124.4(13) . . ? O10 C22 C21 120.2(12) . . ? O9 C22 C21 115.2(13) . . ? C4 N1 C8 116.1(11) . . ? C4 N1 Re1 128.7(9) . . ? C8 N1 Re1 115.2(8) . . ? C9 N2 C10 121.4(11) . . ? C9 N2 Re1 115.3(8) . . ? C10 N2 Re1 123.1(8) . . ? C15 N3 C19 115.8(12) . . ? C15 N3 Re2 127.4(10) . . ? C19 N3 Re2 116.8(10) . . ? C20 N4 C21 117.1(14) . . ? C20 N4 Re2 119.9(10) . . ? C21 N4 Re2 123.0(11) . . ? C11 O7 Re2 123.8(9) . . ? C22 O9 Re1 127.9(9) . . ? C3 Re1 C2 86.6(6) . . ? C3 Re1 C1 88.0(6) . . ? C2 Re1 C1 89.0(6) . . ? C3 Re1 O9 96.3(5) . . ? C2 Re1 O9 173.9(5) . . ? C1 Re1 O9 96.4(5) . . ? C3 Re1 N1 174.9(5) . . ? C2 Re1 N1 94.6(5) . . ? C1 Re1 N1 96.9(5) . . ? O9 Re1 N1 82.0(4) . . ? C3 Re1 N2 99.2(5) . . ? C2 Re1 N2 95.0(5) . . ? C1 Re1 N2 171.9(5) . . ? O9 Re1 N2 79.2(4) . . ? N1 Re1 N2 75.7(4) . . ? C12 Re2 C14 87.5(6) . . ? C12 Re2 C13 84.9(6) . . ? C14 Re2 C13 87.4(6) . . ? C12 Re2 O7 95.6(5) . . ? C14 Re2 O7 175.7(5) . . ? C13 Re2 O7 95.9(5) . . ? C12 Re2 N3 170.4(6) . . ? C14 Re2 N3 95.5(5) . . ? C13 Re2 N3 104.3(5) . . ? O7 Re2 N3 81.0(4) . . ? C12 Re2 N4 96.8(6) . . ? C14 Re2 N4 94.2(5) . . ? C13 Re2 N4 177.7(5) . . ? O7 Re2 N4 82.4(4) . . ? N3 Re2 N4 73.9(5) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.25 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 5.202 _refine_diff_density_min -2.712 _refine_diff_density_rms 0.349 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 810591' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N4 O10 Re2' _chemical_formula_weight 894.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.859(3) _cell_length_b 15.088(5) _cell_length_c 17.416(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2590.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2861 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 22.42 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 9.402 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1648 _exptl_absorpt_correction_T_max 0.8343 _exptl_absorpt_process_details 'SADABS; Sheldrick, 2004 [Sheldrick, G. M. (2004)]' _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.089884 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21369 _diffrn_reflns_av_R_equivalents 0.1107 _diffrn_reflns_av_sigmaI/netI 0.1148 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.25 _reflns_number_total 5761 _reflns_number_gt 4815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms were assigned ideal positions and refined isotropically as riding atoms. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.007(17) _refine_ls_number_reflns 5761 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn 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 -0.2103(13) 0.3154(8) 0.2649(9) 0.040(3) Uani 1 1 d . . . H1 H -0.2730 0.3326 0.3036 0.049 Uiso 1 1 calc R . . C2 C -0.2494(16) 0.3123(10) 0.1862(9) 0.056(5) Uani 1 1 d . . . H2 H -0.3406 0.3242 0.1720 0.067 Uiso 1 1 calc R . . C3 C -0.1553(15) 0.2923(8) 0.1310(8) 0.041(4) Uani 1 1 d . . . H3 H -0.1777 0.2939 0.0780 0.049 Uiso 1 1 calc R . . C4 C -0.0249(14) 0.2696(8) 0.1559(8) 0.035(3) Uani 1 1 d . . . H4 H 0.0400 0.2538 0.1180 0.042 Uiso 1 1 calc R . . C5 C -0.0802(12) 0.2928(8) 0.2832(8) 0.030(3) Uani 1 1 d . . . C6 C -0.0321(13) 0.2892(7) 0.3612(7) 0.024(3) Uani 1 1 d . . . H6 H -0.0915 0.3020 0.4027 0.029 Uiso 1 1 calc R . . C7 C 0.1344(11) 0.2606(8) 0.4546(6) 0.028(2) Uani 1 1 d . . . H7 H 0.0525 0.2700 0.4875 0.033 Uiso 1 1 calc R . . C9 C 0.1894(14) 0.1679(7) 0.4707(7) 0.033(3) Uani 1 1 d . . . H9A H 0.1252 0.1236 0.4515 0.049 Uiso 1 1 calc R . . H9B H 0.2013 0.1602 0.5262 0.049 Uiso 1 1 calc R . . H9C H 0.2769 0.1605 0.4449 0.049 Uiso 1 1 calc R . . C10 C 0.2145(12) 0.1222(8) 0.2809(7) 0.031(3) Uani 1 1 d . . . C11 C 0.3035(14) 0.2344(7) 0.1752(8) 0.035(3) Uani 1 1 d . . . C12 C 0.3883(12) 0.2494(8) 0.3228(7) 0.029(3) Uani 1 1 d . . . C13 C 0.3056(12) 0.4382(7) 0.2519(6) 0.023(2) Uani 1 1 d . . . C14 C 0.2734(12) 0.5382(8) 0.2635(6) 0.029(3) Uani 1 1 d . . . H14A H 0.2029 0.5553 0.2250 0.035 Uiso 1 1 calc R . . C15 C 0.3958(14) 0.5986(8) 0.2519(8) 0.041(4) Uani 1 1 d . . . H15A H 0.3742 0.6583 0.2704 0.062 Uiso 1 1 calc R . . H15B H 0.4186 0.6012 0.1972 0.062 Uiso 1 1 calc R . . H15C H 0.4734 0.5752 0.2807 0.062 Uiso 1 1 calc R . . C16 C 0.4939(12) 0.4959(8) 0.4095(7) 0.029(3) Uani 1 1 d . . . C17 C 0.3740(13) 0.6463(9) 0.4628(7) 0.036(3) Uani 1 1 d . . . C18 C 0.3901(11) 0.5057(7) 0.5505(8) 0.029(3) Uani 1 1 d . . . C19 C 0.2399(12) 0.3328(7) 0.4751(7) 0.027(3) Uani 1 1 d . . . C20 C 0.0875(12) 0.5507(7) 0.3470(6) 0.025(3) Uani 1 1 d . . . H20 H 0.0341 0.5550 0.3017 0.031 Uiso 1 1 calc R . . C21 C 0.0209(11) 0.5505(7) 0.4208(7) 0.021(2) Uani 1 1 d . . . C22 C -0.1171(13) 0.5500(8) 0.4318(8) 0.035(3) Uani 1 1 d . . . H22 H -0.1769 0.5532 0.3892 0.042 Uiso 1 1 calc R . . C23 C -0.1675(13) 0.5447(8) 0.5048(8) 0.036(3) Uani 1 1 d . . . H23 H -0.2625 0.5420 0.5137 0.043 Uiso 1 1 calc R . . C24 C -0.0784(12) 0.5434(8) 0.5641(7) 0.034(3) Uani 1 1 d . . . H24 H -0.1114 0.5394 0.6153 0.040 Uiso 1 1 calc R . . C25 C 0.0581(13) 0.5476(8) 0.5513(7) 0.034(3) Uani 1 1 d . . . H25 H 0.1184 0.5486 0.5939 0.041 Uiso 1 1 calc R . . N1 N 0.0139(9) 0.2685(6) 0.2284(5) 0.023(2) Uani 1 1 d . . . N2 N 0.1083(9) 0.5505(6) 0.4809(5) 0.024(2) Uani 1 1 d . . . N3 N 0.0925(10) 0.2683(6) 0.3740(5) 0.023(2) Uani 1 1 d . . . N4 N 0.2115(10) 0.5453(5) 0.3412(5) 0.024(2) Uani 1 1 d . . . O1 O 0.2140(8) 0.0460(5) 0.2850(5) 0.036(2) Uani 1 1 d . . . O2 O 0.3508(11) 0.2236(6) 0.1149(6) 0.052(3) Uani 1 1 d . . . O3 O 0.4908(8) 0.2538(7) 0.3555(5) 0.036(2) Uani 1 1 d . . . O4 O 0.2033(8) 0.3879(5) 0.2652(4) 0.0255(18) Uani 1 1 d . . . O6 O 0.4389(9) 0.4947(6) 0.6100(5) 0.039(2) Uani 1 1 d . . . O7 O 0.2285(8) 0.4007(5) 0.4343(4) 0.0251(18) Uani 1 1 d . . . O8 O 0.3206(12) 0.3217(6) 0.5283(6) 0.063(3) Uani 1 1 d . . . O9 O 0.4065(9) 0.7200(6) 0.4763(5) 0.038(2) Uani 1 1 d . . . O10 O 0.5993(8) 0.4752(6) 0.3866(5) 0.036(2) Uani 1 1 d . . . O11 O 0.4198(8) 0.4155(5) 0.2287(5) 0.0306(19) Uani 1 1 d . . . Re1 Re 0.32011(4) 0.52757(3) 0.44968(3) 0.02341(12) Uani 1 1 d . . . Re2 Re 0.21631(4) 0.24790(3) 0.27249(3) 0.02399(12) 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 0.026(7) 0.024(6) 0.071(9) 0.000(7) -0.001(7) -0.001(5) C2 0.052(10) 0.042(9) 0.073(11) 0.037(8) -0.013(9) -0.015(7) C3 0.051(9) 0.029(7) 0.042(8) 0.013(6) -0.022(7) -0.008(6) C4 0.036(7) 0.031(8) 0.037(7) -0.003(6) -0.009(6) -0.006(6) C5 0.028(7) 0.022(6) 0.041(7) 0.015(5) -0.004(6) -0.001(5) C6 0.032(7) 0.013(5) 0.029(6) 0.004(5) -0.008(5) 0.004(5) C7 0.032(6) 0.034(7) 0.018(5) 0.006(5) -0.001(5) -0.010(5) C9 0.047(8) 0.019(6) 0.032(6) 0.006(5) -0.013(6) -0.012(6) C10 0.025(7) 0.026(7) 0.042(7) 0.000(5) 0.000(6) 0.003(5) C11 0.039(7) 0.017(6) 0.048(8) -0.005(5) -0.013(6) 0.004(5) C12 0.043(7) 0.009(5) 0.035(7) -0.007(6) 0.019(5) -0.002(6) C13 0.028(7) 0.021(6) 0.021(5) 0.000(4) 0.005(5) -0.003(5) C14 0.036(7) 0.030(6) 0.021(6) 0.009(5) 0.004(5) 0.009(5) C15 0.048(8) 0.029(7) 0.046(9) 0.008(6) 0.017(7) -0.013(6) C16 0.025(7) 0.039(8) 0.022(6) 0.005(5) -0.009(5) -0.003(5) C17 0.039(8) 0.042(8) 0.028(7) 0.008(6) -0.002(6) -0.001(6) C18 0.020(6) 0.033(7) 0.034(7) 0.005(6) 0.006(6) -0.001(5) C19 0.024(6) 0.020(6) 0.035(7) -0.006(5) 0.004(5) 0.002(5) C20 0.028(7) 0.028(7) 0.021(6) 0.000(5) -0.005(5) 0.007(5) C21 0.014(5) 0.014(5) 0.035(6) -0.002(4) 0.002(5) -0.004(4) C22 0.034(7) 0.030(7) 0.041(8) 0.008(6) -0.003(6) 0.002(5) C23 0.016(6) 0.036(7) 0.055(8) -0.006(6) 0.004(6) 0.001(5) C24 0.039(7) 0.029(7) 0.034(7) -0.004(5) 0.004(6) -0.004(5) C25 0.050(8) 0.033(7) 0.020(6) 0.007(6) 0.012(6) -0.005(6) N1 0.022(5) 0.023(5) 0.024(5) 0.003(4) 0.002(4) -0.005(4) N2 0.023(5) 0.025(5) 0.023(5) -0.007(4) 0.001(4) -0.002(4) N3 0.035(6) 0.013(5) 0.021(5) 0.006(4) -0.008(4) -0.008(4) N4 0.041(6) 0.010(4) 0.023(5) 0.000(3) 0.004(4) -0.002(4) O1 0.033(5) 0.024(5) 0.053(5) -0.008(4) -0.010(4) -0.002(4) O2 0.062(7) 0.049(7) 0.045(6) -0.013(5) 0.014(5) -0.009(5) O3 0.020(4) 0.044(5) 0.045(5) -0.017(5) -0.002(4) 0.004(5) O4 0.023(4) 0.019(4) 0.035(4) 0.004(3) -0.004(4) 0.000(3) O6 0.037(5) 0.057(7) 0.022(5) -0.003(4) -0.004(4) 0.009(4) O7 0.028(4) 0.019(4) 0.028(4) 0.000(3) 0.000(3) -0.004(3) O8 0.079(8) 0.027(5) 0.082(8) 0.025(5) -0.060(7) -0.012(5) O9 0.041(5) 0.032(5) 0.041(6) -0.005(4) -0.003(4) -0.008(4) O10 0.031(5) 0.042(5) 0.035(5) 0.006(5) 0.007(4) 0.004(5) O11 0.031(5) 0.023(4) 0.038(5) -0.002(4) 0.009(4) -0.003(3) Re1 0.0254(2) 0.0236(2) 0.0212(2) 0.0000(2) -0.0008(2) -0.0011(2) Re2 0.0237(2) 0.0202(2) 0.0280(2) -0.0008(2) 0.00136(18) -0.0013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C5 1.365(17) . ? C1 C2 1.42(2) . ? C2 C3 1.37(2) . ? C3 C4 1.399(18) . ? C4 N1 1.319(15) . ? C5 N1 1.380(15) . ? C5 C6 1.440(17) . ? C6 N3 1.287(14) . ? C7 N3 1.468(13) . ? C7 C9 1.526(16) . ? C7 C19 1.548(15) . ? C10 O1 1.151(13) . ? C10 Re2 1.902(12) . ? C11 O2 1.161(15) . ? C11 Re2 1.911(14) . ? C12 O3 1.162(13) . ? C12 Re2 1.909(13) . ? C13 O11 1.245(14) . ? C13 O4 1.284(13) . ? C13 C14 1.554(15) . ? C14 N4 1.487(14) . ? C14 C15 1.527(16) . ? C16 O10 1.156(13) . ? C16 Re1 1.912(12) . ? C17 O9 1.181(15) . ? C17 Re1 1.882(14) . ? C18 O6 1.154(14) . ? C18 Re1 1.916(13) . ? C19 O8 1.232(15) . ? C19 O7 1.252(13) . ? C20 N4 1.230(15) . ? C20 C21 1.444(16) . ? C21 N2 1.356(14) . ? C21 C22 1.374(16) . ? C22 C23 1.367(18) . ? C23 C24 1.356(17) . ? C24 C25 1.366(17) . ? C25 N2 1.323(15) . ? N1 Re2 2.161(9) . ? N2 Re1 2.185(9) . ? N3 Re2 2.170(10) . ? N4 Re1 2.188(9) . ? O4 Re2 2.119(7) . ? O7 Re1 2.134(7) . ? 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 C5 C1 C2 118.0(14) . . ? C3 C2 C1 120.0(14) . . ? C2 C3 C4 117.4(13) . . ? N1 C4 C3 124.4(13) . . ? C1 C5 N1 122.5(12) . . ? C1 C5 C6 122.6(13) . . ? N1 C5 C6 114.9(10) . . ? N3 C6 C5 119.1(11) . . ? N3 C7 C9 110.4(10) . . ? N3 C7 C19 110.8(9) . . ? C9 C7 C19 111.3(9) . . ? O1 C10 Re2 179.1(12) . . ? O2 C11 Re2 176.5(11) . . ? O3 C12 Re2 176.7(11) . . ? O11 C13 O4 127.3(10) . . ? O11 C13 C14 119.6(10) . . ? O4 C13 C14 113.0(10) . . ? N4 C14 C15 113.7(10) . . ? N4 C14 C13 105.8(9) . . ? C15 C14 C13 113.6(10) . . ? O10 C16 Re1 178.3(11) . . ? O9 C17 Re1 175.5(11) . . ? O6 C18 Re1 176.2(10) . . ? O8 C19 O7 126.6(11) . . ? O8 C19 C7 120.8(10) . . ? O7 C19 C7 112.6(10) . . ? N4 C20 C21 121.7(11) . . ? N2 C21 C22 121.4(11) . . ? N2 C21 C20 113.5(9) . . ? C22 C21 C20 125.1(11) . . ? C23 C22 C21 119.3(12) . . ? C24 C23 C22 118.3(12) . . ? C23 C24 C25 120.9(12) . . ? N2 C25 C24 121.4(13) . . ? C4 N1 C5 117.6(10) . . ? C4 N1 Re2 127.6(8) . . ? C5 N1 Re2 114.4(7) . . ? C25 N2 C21 118.5(10) . . ? C25 N2 Re1 125.7(8) . . ? C21 N2 Re1 114.5(7) . . ? C6 N3 C7 116.9(10) . . ? C6 N3 Re2 115.5(8) . . ? C7 N3 Re2 127.5(7) . . ? C20 N4 C14 119.2(10) . . ? C20 N4 Re1 115.0(8) . . ? C14 N4 Re1 125.2(8) . . ? C13 O4 Re2 123.6(7) . . ? C19 O7 Re1 128.7(7) . . ? C17 Re1 C16 91.7(5) . . ? C17 Re1 C18 87.2(5) . . ? C16 Re1 C18 88.3(5) . . ? C17 Re1 O7 171.3(5) . . ? C16 Re1 O7 96.3(4) . . ? C18 Re1 O7 96.5(4) . . ? C17 Re1 N2 95.1(5) . . ? C16 Re1 N2 170.8(4) . . ? C18 Re1 N2 98.2(4) . . ? O7 Re1 N2 76.6(3) . . ? C17 Re1 N4 97.2(4) . . ? C16 Re1 N4 98.8(4) . . ? C18 Re1 N4 171.5(4) . . ? O7 Re1 N4 78.1(3) . . ? N2 Re1 N4 74.2(4) . . ? C10 Re2 C12 89.1(5) . . ? C10 Re2 C11 88.1(5) . . ? C12 Re2 C11 90.5(5) . . ? C10 Re2 O4 175.9(4) . . ? C12 Re2 O4 94.0(4) . . ? C11 Re2 O4 94.6(4) . . ? C10 Re2 N1 99.3(4) . . ? C12 Re2 N1 169.1(4) . . ? C11 Re2 N1 96.6(4) . . ? O4 Re2 N1 77.3(3) . . ? C10 Re2 N3 94.2(4) . . ? C12 Re2 N3 97.1(4) . . ? C11 Re2 N3 172.1(4) . . ? O4 Re2 N3 82.7(3) . . ? N1 Re2 N3 75.5(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.444 _refine_diff_density_min -1.105 _refine_diff_density_rms 0.220