# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 _publ_contact_author_name J.R.Gardinier _publ_contact_author_email james.gardinier@marquette.edu _publ_contact_author_address ; ; loop_ _publ_author_name S.Wanniarachchi B.J.Liddle J.Toussaint S.V.Lindeman B.Bennett J.R.Gardinier #TrackingRef 'Re_Pincer_full.cif' _publ_requested_journal ? # Attachment 'Re_Pincer_full.cif' data_gard9u_HLMe _database_code_depnum_ccdc_archive 'CCDC 806478' #TrackingRef 'Re_Pincer_full.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N5' _chemical_formula_weight 357.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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 b c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.6980(3) _cell_length_b 7.7505(2) _cell_length_c 33.6382(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3831.96(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9951 _cell_measurement_theta_min 3 _cell_measurement_theta_max 67 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.597 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7835 _exptl_absorpt_correction_T_max 0.9318 _exptl_absorpt_process_details ; SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 32005 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 67.97 _reflns_number_total 3444 _reflns_number_gt 3072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2-2009.3-0 (Bruker, 2009)' _computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)' _computing_data_reduction 'SADABS-2008/1 (Bruker, 2008)' _computing_structure_solution 'XS/SHELXTL-2008/4 (Bruker, 2008)' _computing_structure_refinement 'SHELXL-2008/4(Bruker, 2008)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF-2008/2 (Bruker, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+1.6557P] 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 SHELXL _refine_ls_extinction_coef 0.00043(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3444 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 N1 N 0.49588(8) 0.17034(16) 0.42209(3) 0.0301(3) Uani 1 1 d . . . N2 N 0.55500(8) 0.04262(15) 0.43227(3) 0.0263(3) Uani 1 1 d . . . N3 N 0.49806(8) 0.43314(15) 0.33563(3) 0.0268(3) Uani 1 1 d . . . N4 N 0.56099(7) 0.43951(14) 0.30579(3) 0.0240(3) Uani 1 1 d . . . N5 N 0.62347(8) 0.17692(16) 0.35894(3) 0.0276(3) Uani 1 1 d . . . H5N H 0.5764(12) 0.233(2) 0.3668(5) 0.032(4) Uiso 1 1 d . . . C1 C 0.41411(10) 0.1106(2) 0.43325(4) 0.0316(3) Uani 1 1 d . . . C2 C 0.42143(11) -0.0525(2) 0.45037(4) 0.0350(4) Uani 1 1 d . . . H2A H 0.3734 -0.1216 0.4606 0.042 Uiso 1 1 calc R . . C3 C 0.51198(11) -0.09240(19) 0.44943(4) 0.0328(3) Uani 1 1 d . . . H3A H 0.5394 -0.1953 0.4590 0.039 Uiso 1 1 calc R . . C4 C 0.65063(9) 0.05749(16) 0.42490(4) 0.0251(3) Uani 1 1 d . . . C5 C 0.71024(10) 0.00511(17) 0.45459(4) 0.0263(3) Uani 1 1 d . . . H5A H 0.6864 -0.0313 0.4795 0.032 Uiso 1 1 calc R . . C6 C 0.80371(10) 0.00463(17) 0.44889(4) 0.0269(3) Uani 1 1 d . . . C7 C 0.83587(9) 0.05856(17) 0.41195(4) 0.0265(3) Uani 1 1 d . . . H7A H 0.8994 0.0563 0.4069 0.032 Uiso 1 1 calc R . . C8 C 0.77751(9) 0.11515(17) 0.38256(4) 0.0256(3) Uani 1 1 d . . . H8A H 0.8020 0.1542 0.3580 0.031 Uiso 1 1 calc R . . C9 C 0.68295(9) 0.11639(17) 0.38809(4) 0.0244(3) Uani 1 1 d . . . C10 C 0.86787(11) -0.0495(2) 0.48160(4) 0.0337(3) Uani 1 1 d . . . H10A H 0.8349 -0.1196 0.5011 0.051 Uiso 1 1 calc R . . H10B H 0.8926 0.0533 0.4947 0.051 Uiso 1 1 calc R . . H10C H 0.9178 -0.1174 0.4703 0.051 Uiso 1 1 calc R . . C11 C 0.46914(10) 0.59554(19) 0.33965(4) 0.0310(3) Uani 1 1 d . . . C12 C 0.51274(10) 0.70471(19) 0.31260(5) 0.0384(4) Uani 1 1 d . . . H12A H 0.5040 0.8254 0.3095 0.046 Uiso 1 1 calc R . . C13 C 0.57061(10) 0.60155(19) 0.29146(5) 0.0338(3) Uani 1 1 d . . . H13A H 0.6101 0.6369 0.2706 0.041 Uiso 1 1 calc R . . C14 C 0.60327(8) 0.28615(17) 0.29147(4) 0.0228(3) Uani 1 1 d . . . C15 C 0.61209(9) 0.26536(18) 0.25061(4) 0.0256(3) Uani 1 1 d . . . H15A H 0.5878 0.3509 0.2334 0.031 Uiso 1 1 calc R . . C16 C 0.65547(9) 0.12281(19) 0.23427(4) 0.0280(3) Uani 1 1 d . . . C17 C 0.68960(9) 0.00010(19) 0.26058(4) 0.0287(3) Uani 1 1 d . . . H17A H 0.7197 -0.0988 0.2503 0.034 Uiso 1 1 calc R . . C18 C 0.68066(9) 0.01874(18) 0.30138(4) 0.0267(3) Uani 1 1 d . . . H18A H 0.7050 -0.0675 0.3184 0.032 Uiso 1 1 calc R . . C19 C 0.63674(8) 0.16128(17) 0.31805(4) 0.0230(3) Uani 1 1 d . . . C20 C 0.66482(11) 0.1035(2) 0.18981(4) 0.0393(4) Uani 1 1 d . . . H20A H 0.6059 0.1253 0.1771 0.059 Uiso 1 1 calc R . . H20B H 0.6849 -0.0139 0.1835 0.059 Uiso 1 1 calc R . . H20C H 0.7097 0.1865 0.1799 0.059 Uiso 1 1 calc R . . C21 C 0.33039(10) 0.2155(2) 0.42632(5) 0.0433(4) Uani 1 1 d . . . H21A H 0.3397 0.2911 0.4033 0.065 Uiso 1 1 calc R . . H21B H 0.3177 0.2858 0.4499 0.065 Uiso 1 1 calc R . . H21C H 0.2788 0.1385 0.4212 0.065 Uiso 1 1 calc R . . C22 C 0.39941(11) 0.6388(2) 0.37052(5) 0.0425(4) Uani 1 1 d . . . H22A H 0.4200 0.5969 0.3965 0.064 Uiso 1 1 calc R . . H22B H 0.3415 0.5835 0.3637 0.064 Uiso 1 1 calc R . . H22C H 0.3911 0.7641 0.3716 0.064 Uiso 1 1 calc R . . 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 N1 0.0247(6) 0.0357(7) 0.0299(6) -0.0013(5) 0.0024(5) 0.0011(5) N2 0.0263(6) 0.0275(6) 0.0252(6) -0.0018(5) 0.0043(5) -0.0011(5) N3 0.0246(6) 0.0308(6) 0.0252(6) -0.0050(5) -0.0026(5) 0.0048(5) N4 0.0203(5) 0.0239(6) 0.0279(6) -0.0004(4) -0.0040(4) 0.0011(4) N5 0.0262(6) 0.0296(6) 0.0270(6) 0.0026(5) 0.0040(5) 0.0074(5) C1 0.0253(7) 0.0434(9) 0.0262(7) -0.0107(6) 0.0028(6) -0.0043(6) C2 0.0344(8) 0.0383(8) 0.0322(8) -0.0077(6) 0.0107(6) -0.0112(7) C3 0.0376(8) 0.0299(7) 0.0309(7) -0.0019(6) 0.0096(6) -0.0051(6) C4 0.0257(7) 0.0212(6) 0.0284(7) -0.0025(5) 0.0051(6) 0.0001(5) C5 0.0334(7) 0.0228(7) 0.0229(6) -0.0004(5) 0.0050(6) 0.0003(6) C6 0.0306(7) 0.0222(7) 0.0279(7) -0.0029(5) -0.0004(6) 0.0026(5) C7 0.0247(7) 0.0234(7) 0.0314(7) -0.0025(5) 0.0027(6) 0.0009(5) C8 0.0280(7) 0.0230(7) 0.0258(7) 0.0011(5) 0.0061(6) -0.0004(5) C9 0.0271(7) 0.0200(6) 0.0260(7) -0.0002(5) 0.0027(6) 0.0014(5) C10 0.0359(8) 0.0357(8) 0.0295(7) -0.0002(6) -0.0010(6) 0.0045(6) C11 0.0265(7) 0.0319(8) 0.0345(8) -0.0100(6) -0.0116(6) 0.0067(6) C12 0.0307(8) 0.0238(7) 0.0607(10) -0.0007(7) -0.0079(7) 0.0060(6) C13 0.0256(7) 0.0262(7) 0.0495(9) 0.0070(6) -0.0031(6) 0.0010(6) C14 0.0159(6) 0.0231(6) 0.0293(7) -0.0013(5) -0.0012(5) -0.0024(5) C15 0.0182(6) 0.0311(7) 0.0276(7) 0.0018(6) -0.0024(5) -0.0021(5) C16 0.0185(6) 0.0370(8) 0.0286(7) -0.0045(6) 0.0009(5) -0.0040(6) C17 0.0208(6) 0.0281(7) 0.0372(8) -0.0078(6) 0.0027(6) -0.0003(5) C18 0.0239(6) 0.0223(7) 0.0338(7) 0.0019(6) 0.0001(6) 0.0002(5) C19 0.0182(6) 0.0228(6) 0.0279(7) 0.0009(5) 0.0009(5) -0.0037(5) C20 0.0321(8) 0.0537(10) 0.0322(8) -0.0076(7) 0.0036(7) 0.0021(7) C21 0.0262(8) 0.0592(11) 0.0445(9) -0.0036(8) 0.0018(7) -0.0002(7) C22 0.0401(9) 0.0479(10) 0.0394(9) -0.0143(7) -0.0073(7) 0.0177(7) _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 N1 C1 1.3413(18) . ? N1 N2 1.3610(16) . ? N2 C3 1.3521(19) . ? N2 C4 1.4319(18) . ? N3 C11 1.3354(18) . ? N3 N4 1.3657(16) . ? N4 C13 1.3527(18) . ? N4 C14 1.4252(17) . ? N5 C19 1.3942(18) . ? N5 C9 1.3950(18) . ? N5 H5N 0.858(18) . ? C1 C2 1.393(2) . ? C1 C21 1.493(2) . ? C2 C3 1.367(2) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C5 1.389(2) . ? C4 C9 1.4026(19) . ? C5 C6 1.387(2) . ? C5 H5A 0.9500 . ? C6 C7 1.394(2) . ? C6 C10 1.509(2) . ? C7 C8 1.3803(19) . ? C7 H7A 0.9500 . ? C8 C9 1.4021(19) . ? C8 H8A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.398(2) . ? C11 C22 1.497(2) . ? C12 C13 1.367(2) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.3898(19) . ? C14 C19 1.4065(19) . ? C15 C16 1.389(2) . ? C15 H15A 0.9500 . ? C16 C17 1.393(2) . ? C16 C20 1.509(2) . ? C17 C18 1.386(2) . ? C17 H17A 0.9500 . ? C18 C19 1.3972(19) . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 104.52(12) . . ? C3 N2 N1 111.82(12) . . ? C3 N2 C4 126.53(12) . . ? N1 N2 C4 121.64(11) . . ? C11 N3 N4 104.83(12) . . ? C13 N4 N3 111.49(11) . . ? C13 N4 C14 127.46(12) . . ? N3 N4 C14 120.90(11) . . ? C19 N5 C9 125.21(12) . . ? C19 N5 H5N 117.4(11) . . ? C9 N5 H5N 117.3(11) . . ? N1 C1 C2 111.07(13) . . ? N1 C1 C21 120.46(14) . . ? C2 C1 C21 128.47(14) . . ? C3 C2 C1 105.73(13) . . ? C3 C2 H2A 127.1 . . ? C1 C2 H2A 127.1 . . ? N2 C3 C2 106.85(14) . . ? N2 C3 H3A 126.6 . . ? C2 C3 H3A 126.6 . . ? C5 C4 C9 121.08(13) . . ? C5 C4 N2 118.10(12) . . ? C9 C4 N2 120.77(12) . . ? C6 C5 C4 121.73(13) . . ? C6 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? C5 C6 C7 117.29(13) . . ? C5 C6 C10 121.26(13) . . ? C7 C6 C10 121.44(13) . . ? C8 C7 C6 121.53(13) . . ? C8 C7 H7A 119.2 . . ? C6 C7 H7A 119.2 . . ? C7 C8 C9 121.55(12) . . ? C7 C8 H8A 119.2 . . ? C9 C8 H8A 119.2 . . ? N5 C9 C8 122.02(12) . . ? N5 C9 C4 121.18(12) . . ? C8 C9 C4 116.78(12) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 111.01(13) . . ? N3 C11 C22 119.95(14) . . ? C12 C11 C22 129.04(14) . . ? C13 C12 C11 105.66(13) . . ? C13 C12 H12A 127.2 . . ? C11 C12 H12A 127.2 . . ? N4 C13 C12 107.01(14) . . ? N4 C13 H13A 126.5 . . ? C12 C13 H13A 126.5 . . ? C15 C14 C19 121.09(12) . . ? C15 C14 N4 118.14(12) . . ? C19 C14 N4 120.75(12) . . ? C16 C15 C14 121.76(13) . . ? C16 C15 H15A 119.1 . . ? C14 C15 H15A 119.1 . . ? C15 C16 C17 117.20(13) . . ? C15 C16 C20 120.85(13) . . ? C17 C16 C20 121.95(13) . . ? C18 C17 C16 121.59(13) . . ? C18 C17 H17A 119.2 . . ? C16 C17 H17A 119.2 . . ? C17 C18 C19 121.58(13) . . ? C17 C18 H18A 119.2 . . ? C19 C18 H18A 119.2 . . ? N5 C19 C18 121.96(12) . . ? N5 C19 C14 121.23(12) . . ? C18 C19 C14 116.76(12) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 C21 H21A 109.5 . . ? C1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C11 C22 H22A 109.5 . . ? C11 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C11 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 C1 N1 N2 C3 -0.31(15) . . . . ? C1 N1 N2 C4 179.73(12) . . . . ? C11 N3 N4 C13 -0.35(15) . . . . ? C11 N3 N4 C14 -176.27(11) . . . . ? N2 N1 C1 C2 0.17(15) . . . . ? N2 N1 C1 C21 -179.16(13) . . . . ? N1 C1 C2 C3 0.01(16) . . . . ? C21 C1 C2 C3 179.28(15) . . . . ? N1 N2 C3 C2 0.33(16) . . . . ? C4 N2 C3 C2 -179.72(13) . . . . ? C1 C2 C3 N2 -0.20(16) . . . . ? C3 N2 C4 C5 -42.98(19) . . . . ? N1 N2 C4 C5 136.97(13) . . . . ? C3 N2 C4 C9 134.36(14) . . . . ? N1 N2 C4 C9 -45.69(18) . . . . ? C9 C4 C5 C6 -1.6(2) . . . . ? N2 C4 C5 C6 175.72(12) . . . . ? C4 C5 C6 C7 -0.2(2) . . . . ? C4 C5 C6 C10 178.90(13) . . . . ? C5 C6 C7 C8 1.9(2) . . . . ? C10 C6 C7 C8 -177.19(13) . . . . ? C6 C7 C8 C9 -1.8(2) . . . . ? C19 N5 C9 C8 33.8(2) . . . . ? C19 N5 C9 C4 -147.77(13) . . . . ? C7 C8 C9 N5 178.53(12) . . . . ? C7 C8 C9 C4 0.04(19) . . . . ? C5 C4 C9 N5 -176.85(12) . . . . ? N2 C4 C9 N5 5.89(19) . . . . ? C5 C4 C9 C8 1.65(19) . . . . ? N2 C4 C9 C8 -175.60(12) . . . . ? N4 N3 C11 C12 0.25(15) . . . . ? N4 N3 C11 C22 -179.25(12) . . . . ? N3 C11 C12 C13 -0.06(17) . . . . ? C22 C11 C12 C13 179.37(14) . . . . ? N3 N4 C13 C12 0.32(16) . . . . ? C14 N4 C13 C12 175.91(13) . . . . ? C11 C12 C13 N4 -0.16(17) . . . . ? C13 N4 C14 C15 -39.31(19) . . . . ? N3 N4 C14 C15 135.90(12) . . . . ? C13 N4 C14 C19 139.40(14) . . . . ? N3 N4 C14 C19 -45.38(17) . . . . ? C19 C14 C15 C16 -1.15(19) . . . . ? N4 C14 C15 C16 177.56(12) . . . . ? C14 C15 C16 C17 0.35(19) . . . . ? C14 C15 C16 C20 -179.58(13) . . . . ? C15 C16 C17 C18 0.1(2) . . . . ? C20 C16 C17 C18 -179.94(13) . . . . ? C16 C17 C18 C19 0.2(2) . . . . ? C9 N5 C19 C18 33.4(2) . . . . ? C9 N5 C19 C14 -148.95(13) . . . . ? C17 C18 C19 N5 176.77(12) . . . . ? C17 C18 C19 C14 -0.94(19) . . . . ? C15 C14 C19 N5 -176.32(12) . . . . ? N4 C14 C19 N5 5.00(18) . . . . ? C15 C14 C19 C18 1.40(18) . . . . ? N4 C14 C19 C18 -177.28(11) . . . . ? 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 N5 H5N N1 0.858(18) 2.258(17) 2.8342(16) 124.6(14) . N5 H5N N3 0.858(18) 2.198(17) 2.8207(16) 129.2(14) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.237 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.036 #===END data_gard8ja_1Me _database_code_depnum_ccdc_archive 'CCDC 806479' #TrackingRef 'Re_Pincer_full.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H29 Br N5 O4 Re' _chemical_formula_weight 765.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -5.2083 5.8923 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8094(2) _cell_length_b 10.9596(2) _cell_length_c 13.4496(2) _cell_angle_alpha 84.7710(10) _cell_angle_beta 85.0860(10) _cell_angle_gamma 60.9190(10) _cell_volume 1385.10(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5019 _cell_measurement_theta_min 3 _cell_measurement_theta_max 67 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.836 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 10.630 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.1847 _exptl_absorpt_correction_T_max 0.6185 _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11557 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 67.89 _reflns_number_total 4733 _reflns_number_gt 4706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0265P)^2^+2.2860P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00039(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4733 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0173 _refine_ls_R_factor_gt 0.0172 _refine_ls_wR_factor_ref 0.0447 _refine_ls_wR_factor_gt 0.0446 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.437082(10) 0.197549(10) 0.187118(7) 0.00981(5) Uani 1 1 d . . . Br1 Br 0.24854(3) 0.22195(3) 0.332344(19) 0.01607(7) Uani 1 1 d . . . O1 O 0.5194(2) -0.0976(2) 0.13046(16) 0.0248(4) Uani 1 1 d . . . O2 O 0.2080(2) 0.2910(2) 0.03447(14) 0.0202(4) Uani 1 1 d . . . O3 O 0.6415(2) 0.20185(19) 0.01816(14) 0.0191(4) Uani 1 1 d . . . N1 N 0.5882(2) 0.1374(2) 0.30520(16) 0.0122(4) Uani 1 1 d . . . N2 N 0.6488(2) 0.2179(2) 0.32398(15) 0.0122(4) Uani 1 1 d . . . N3 N 0.3121(2) 0.4938(2) 0.42531(16) 0.0141(4) Uani 1 1 d . . . N4 N 0.1782(2) 0.5740(2) 0.39087(16) 0.0134(4) Uani 1 1 d . . . N5 N 0.3905(2) 0.4084(2) 0.23736(16) 0.0109(4) Uani 1 1 d . . . H5N H 0.389(3) 0.393(3) 0.297(3) 0.016(8) Uiso 1 1 d . . . C1 C 0.6339(3) 0.0326(3) 0.37670(19) 0.0147(5) Uani 1 1 d . . . C2 C 0.7218(3) 0.0466(3) 0.4398(2) 0.0171(5) Uani 1 1 d . . . H2A H 0.7674 -0.0135 0.4959 0.021 Uiso 1 1 calc R . . C3 C 0.7289(3) 0.1641(3) 0.40483(19) 0.0163(5) Uani 1 1 d . . . H3A H 0.7808 0.2013 0.4323 0.020 Uiso 1 1 calc R . . C4 C 0.6415(3) 0.3301(3) 0.25737(18) 0.0118(5) Uani 1 1 d . . . C5 C 0.7650(3) 0.3408(3) 0.23898(18) 0.0128(5) Uani 1 1 d . . . H5A H 0.8509 0.2709 0.2666 0.015 Uiso 1 1 calc R . . C6 C 0.7634(3) 0.4532(3) 0.18040(18) 0.0134(5) Uani 1 1 d . . . C7 C 0.6354(3) 0.5514(3) 0.13897(18) 0.0136(5) Uani 1 1 d . . . H7A H 0.6320 0.6288 0.0987 0.016 Uiso 1 1 calc R . . C8 C 0.5134(3) 0.5389(3) 0.15516(18) 0.0128(5) Uani 1 1 d . . . H8A H 0.4287 0.6062 0.1247 0.015 Uiso 1 1 calc R . . C9 C 0.5142(3) 0.4284(3) 0.21563(18) 0.0115(5) Uani 1 1 d . . . C10 C 0.8946(3) 0.4693(3) 0.1631(2) 0.0178(5) Uani 1 1 d . . . H10A H 0.8776 0.5560 0.1910 0.027 Uiso 1 1 calc R . . H10B H 0.9174 0.4730 0.0911 0.027 Uiso 1 1 calc R . . H10C H 0.9740 0.3895 0.1958 0.027 Uiso 1 1 calc R . . C11 C 0.2943(3) 0.4781(3) 0.52354(19) 0.0159(5) Uani 1 1 d . . . C12 C 0.1499(3) 0.5475(3) 0.5534(2) 0.0215(6) Uani 1 1 d . . . H12A H 0.1096 0.5521 0.6195 0.026 Uiso 1 1 calc R . . C13 C 0.0793(3) 0.6071(3) 0.4678(2) 0.0193(6) Uani 1 1 d . . . H13A H -0.0205 0.6615 0.4628 0.023 Uiso 1 1 calc R . . C14 C 0.1562(3) 0.6085(3) 0.28736(19) 0.0127(5) Uani 1 1 d . . . C15 C 0.0303(3) 0.7259(3) 0.25921(19) 0.0153(5) Uani 1 1 d . . . H15A H -0.0361 0.7798 0.3097 0.018 Uiso 1 1 calc R . . C16 C -0.0006(3) 0.7662(3) 0.1600(2) 0.0159(5) Uani 1 1 d . . . C17 C 0.0978(3) 0.6851(3) 0.08676(19) 0.0155(5) Uani 1 1 d . . . H17A H 0.0787 0.7101 0.0181 0.019 Uiso 1 1 calc R . . C18 C 0.2229(3) 0.5687(3) 0.11380(19) 0.0148(5) Uani 1 1 d . . . H18A H 0.2883 0.5145 0.0630 0.018 Uiso 1 1 calc R . . C19 C 0.2552(3) 0.5291(3) 0.21313(19) 0.0120(5) Uani 1 1 d . . . C20 C -0.1356(3) 0.8954(3) 0.1315(2) 0.0230(6) Uani 1 1 d . . . H20A H -0.1742 0.9559 0.1881 0.035 Uiso 1 1 calc R . . H20B H -0.2048 0.8685 0.1140 0.035 Uiso 1 1 calc R . . H20C H -0.1157 0.9460 0.0741 0.035 Uiso 1 1 calc R . . C21 C 0.4888(3) 0.0119(3) 0.1540(2) 0.0173(5) Uani 1 1 d . . . C22 C 0.2929(3) 0.2590(3) 0.09167(19) 0.0139(5) Uani 1 1 d . . . C23 C 0.5680(3) 0.1998(3) 0.08073(19) 0.0139(5) Uani 1 1 d . . . C24 C 0.5964(3) -0.0822(3) 0.3818(2) 0.0196(6) Uani 1 1 d . . . H24A H 0.4934 -0.0419 0.3800 0.029 Uiso 1 1 calc R . . H24B H 0.6291 -0.1397 0.4440 0.029 Uiso 1 1 calc R . . H24C H 0.6422 -0.1405 0.3246 0.029 Uiso 1 1 calc R . . C25 C 0.4209(3) 0.3945(3) 0.58484(19) 0.0180(5) Uani 1 1 d . . . H25A H 0.4861 0.3082 0.5521 0.027 Uiso 1 1 calc R . . H25B H 0.3908 0.3713 0.6513 0.027 Uiso 1 1 calc R . . H25C H 0.4691 0.4493 0.5913 0.027 Uiso 1 1 calc R . . O1S O 0.0244(2) 0.0262(2) 0.32222(18) 0.0369(6) Uani 1 1 d . . . C1S C 0.1273(3) -0.0239(3) 0.2659(2) 0.0216(6) Uani 1 1 d . . . C2S C 0.2667(3) -0.1401(3) 0.3003(2) 0.0253(6) Uani 1 1 d . . . H2SA H 0.2517 -0.1826 0.3643 0.038 Uiso 1 1 calc R . . H2SB H 0.3307 -0.1024 0.3087 0.038 Uiso 1 1 calc R . . H2SC H 0.3089 -0.2110 0.2504 0.038 Uiso 1 1 calc R . . C3S C 0.1234(3) 0.0274(3) 0.1587(2) 0.0291(7) Uani 1 1 d . . . H3SA H 0.0257 0.0949 0.1427 0.044 Uiso 1 1 calc R . . H3SB H 0.1593 -0.0518 0.1159 0.044 Uiso 1 1 calc R . . H3SC H 0.1828 0.0726 0.1472 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.00973(7) 0.00870(7) 0.01023(7) 0.00002(4) 0.00019(4) -0.00402(5) Br1 0.01504(13) 0.01665(14) 0.01612(14) 0.00084(10) 0.00262(10) -0.00815(11) O1 0.0273(11) 0.0146(11) 0.0338(11) -0.0071(8) 0.0011(9) -0.0106(9) O2 0.0178(9) 0.0238(10) 0.0199(10) 0.0012(8) -0.0052(8) -0.0104(8) O3 0.0172(9) 0.0163(10) 0.0203(10) 0.0032(7) 0.0006(8) -0.0062(8) N1 0.0119(10) 0.0110(11) 0.0135(10) 0.0000(8) -0.0004(8) -0.0054(9) N2 0.0115(10) 0.0113(11) 0.0139(10) 0.0009(8) -0.0009(8) -0.0058(9) N3 0.0145(10) 0.0137(11) 0.0135(11) -0.0001(8) -0.0015(8) -0.0061(9) N4 0.0112(10) 0.0149(11) 0.0138(11) -0.0018(8) -0.0013(8) -0.0057(9) N5 0.0131(10) 0.0099(11) 0.0089(11) -0.0009(8) 0.0009(8) -0.0050(9) C1 0.0138(12) 0.0123(13) 0.0132(12) 0.0036(9) 0.0025(9) -0.0038(10) C2 0.0147(12) 0.0168(13) 0.0158(13) 0.0061(10) -0.0019(10) -0.0055(11) C3 0.0143(12) 0.0185(14) 0.0157(13) 0.0020(10) -0.0030(10) -0.0076(11) C4 0.0145(12) 0.0112(12) 0.0095(11) -0.0017(9) 0.0017(9) -0.0062(10) C5 0.0133(12) 0.0129(13) 0.0109(12) -0.0010(9) 0.0011(9) -0.0055(10) C6 0.0166(12) 0.0152(13) 0.0091(12) -0.0028(9) 0.0023(9) -0.0084(11) C7 0.0191(12) 0.0115(12) 0.0099(12) -0.0005(9) 0.0008(9) -0.0074(11) C8 0.0139(12) 0.0106(12) 0.0100(11) -0.0019(9) 0.0007(9) -0.0028(10) C9 0.0118(11) 0.0115(12) 0.0103(11) -0.0031(9) 0.0010(9) -0.0046(10) C10 0.0180(13) 0.0209(14) 0.0177(13) 0.0009(10) 0.0004(10) -0.0124(11) C11 0.0204(13) 0.0165(13) 0.0143(12) -0.0034(10) 0.0010(10) -0.0114(11) C12 0.0236(14) 0.0289(16) 0.0134(13) -0.0033(11) 0.0037(11) -0.0140(13) C13 0.0132(12) 0.0267(15) 0.0161(13) -0.0036(11) 0.0038(10) -0.0086(12) C14 0.0129(12) 0.0148(13) 0.0130(12) 0.0000(9) -0.0002(9) -0.0090(10) C15 0.0125(12) 0.0144(13) 0.0183(13) -0.0043(10) 0.0013(10) -0.0057(11) C16 0.0143(12) 0.0153(13) 0.0190(13) -0.0003(10) -0.0029(10) -0.0076(11) C17 0.0161(12) 0.0163(13) 0.0141(12) 0.0018(10) -0.0038(10) -0.0079(11) C18 0.0158(12) 0.0155(13) 0.0142(12) -0.0019(10) 0.0013(10) -0.0085(11) C19 0.0110(11) 0.0089(12) 0.0167(12) -0.0004(9) -0.0001(9) -0.0054(10) C20 0.0158(13) 0.0208(15) 0.0238(15) -0.0013(11) -0.0051(11) -0.0015(12) C21 0.0138(12) 0.0179(15) 0.0194(14) 0.0001(11) -0.0015(10) -0.0069(11) C22 0.0139(12) 0.0130(13) 0.0144(12) -0.0017(10) 0.0023(10) -0.0063(10) C23 0.0150(12) 0.0069(12) 0.0148(13) -0.0024(9) -0.0063(11) -0.0003(10) C24 0.0221(13) 0.0155(14) 0.0212(14) 0.0060(10) -0.0038(11) -0.0098(11) C25 0.0210(13) 0.0197(14) 0.0136(12) -0.0008(10) -0.0018(10) -0.0100(12) O1S 0.0272(12) 0.0316(13) 0.0360(13) 0.0016(10) 0.0124(10) -0.0044(10) C1S 0.0215(14) 0.0168(14) 0.0288(15) -0.0041(11) 0.0024(12) -0.0110(12) C2S 0.0234(14) 0.0210(15) 0.0322(16) -0.0034(12) -0.0031(12) -0.0106(13) C3S 0.0303(16) 0.0285(17) 0.0279(16) -0.0008(13) -0.0005(13) -0.0140(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C21 1.915(3) . ? Re1 C22 1.922(3) . ? Re1 C23 1.932(3) . ? Re1 N1 2.198(2) . ? Re1 N5 2.268(2) . ? Re1 Br1 2.6312(3) . ? O1 C21 1.147(3) . ? O2 C22 1.147(3) . ? O3 C23 1.113(3) . ? N1 C1 1.348(3) . ? N1 N2 1.378(3) . ? N2 C3 1.352(3) . ? N2 C4 1.428(3) . ? N3 C11 1.326(3) . ? N3 N4 1.374(3) . ? N4 C13 1.359(3) . ? N4 C14 1.418(3) . ? N5 C19 1.456(3) . ? N5 C9 1.459(3) . ? N5 H5N 0.80(3) . ? C1 C2 1.397(4) . ? C1 C24 1.493(4) . ? C2 C3 1.366(4) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C5 1.396(3) . ? C4 C9 1.396(3) . ? C5 C6 1.394(4) . ? C5 H5A 0.9500 . ? C6 C7 1.400(4) . ? C6 C10 1.509(3) . ? C7 C8 1.389(4) . ? C7 H7A 0.9500 . ? C8 C9 1.392(4) . ? C8 H8A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.404(4) . ? C11 C25 1.493(4) . ? C12 C13 1.366(4) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.396(4) . ? C14 C19 1.403(4) . ? C15 C16 1.383(4) . ? C15 H15A 0.9500 . ? C16 C17 1.397(4) . ? C16 C20 1.507(4) . ? C17 C18 1.382(4) . ? C17 H17A 0.9500 . ? C18 C19 1.386(4) . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? O1S C1S 1.204(4) . ? C1S C3S 1.496(4) . ? C1S C2S 1.501(4) . ? C2S H2SA 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SC 0.9800 . ? C3S H3SA 0.9800 . ? C3S H3SB 0.9800 . ? C3S H3SC 0.9800 . ? 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 C21 Re1 C22 85.90(11) . . ? C21 Re1 C23 88.03(11) . . ? C22 Re1 C23 89.42(10) . . ? C21 Re1 N1 96.85(10) . . ? C22 Re1 N1 175.32(9) . . ? C23 Re1 N1 94.44(9) . . ? C21 Re1 N5 174.76(9) . . ? C22 Re1 N5 99.31(9) . . ? C23 Re1 N5 92.56(9) . . ? N1 Re1 N5 77.91(8) . . ? C21 Re1 Br1 97.60(8) . . ? C22 Re1 Br1 89.65(7) . . ? C23 Re1 Br1 174.22(7) . . ? N1 Re1 Br1 86.24(5) . . ? N5 Re1 Br1 81.96(5) . . ? C1 N1 N2 105.1(2) . . ? C1 N1 Re1 132.42(17) . . ? N2 N1 Re1 122.25(15) . . ? C3 N2 N1 110.7(2) . . ? C3 N2 C4 125.8(2) . . ? N1 N2 C4 122.9(2) . . ? C11 N3 N4 105.6(2) . . ? C13 N4 N3 110.6(2) . . ? C13 N4 C14 128.2(2) . . ? N3 N4 C14 121.2(2) . . ? C19 N5 C9 115.32(19) . . ? C19 N5 Re1 118.00(15) . . ? C9 N5 Re1 109.92(14) . . ? C19 N5 H5N 108(2) . . ? C9 N5 H5N 104(2) . . ? Re1 N5 H5N 99(2) . . ? N1 C1 C2 110.4(2) . . ? N1 C1 C24 122.7(2) . . ? C2 C1 C24 126.9(2) . . ? C3 C2 C1 106.2(2) . . ? C3 C2 H2A 126.9 . . ? C1 C2 H2A 126.9 . . ? N2 C3 C2 107.6(2) . . ? N2 C3 H3A 126.2 . . ? C2 C3 H3A 126.2 . . ? C5 C4 C9 121.4(2) . . ? C5 C4 N2 117.4(2) . . ? C9 C4 N2 121.2(2) . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 117.7(2) . . ? C5 C6 C10 121.2(2) . . ? C7 C6 C10 121.1(2) . . ? C8 C7 C6 121.8(2) . . ? C8 C7 H7A 119.1 . . ? C6 C7 H7A 119.1 . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H8A 119.7 . . ? C9 C8 H8A 119.7 . . ? C8 C9 C4 118.0(2) . . ? C8 C9 N5 124.0(2) . . ? C4 C9 N5 117.9(2) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 110.8(2) . . ? N3 C11 C25 119.4(2) . . ? C12 C11 C25 129.8(2) . . ? C13 C12 C11 105.7(2) . . ? C13 C12 H12A 127.1 . . ? C11 C12 H12A 127.1 . . ? N4 C13 C12 107.3(2) . . ? N4 C13 H13A 126.4 . . ? C12 C13 H13A 126.4 . . ? C15 C14 C19 119.3(2) . . ? C15 C14 N4 118.1(2) . . ? C19 C14 N4 122.6(2) . . ? C16 C15 C14 121.9(2) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C15 C16 C17 118.2(2) . . ? C15 C16 C20 120.9(2) . . ? C17 C16 C20 120.9(2) . . ? C18 C17 C16 120.3(2) . . ? C18 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? C17 C18 C19 121.7(2) . . ? C17 C18 H18A 119.2 . . ? C19 C18 H18A 119.2 . . ? C18 C19 C14 118.5(2) . . ? C18 C19 N5 119.4(2) . . ? C14 C19 N5 122.0(2) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 Re1 177.4(2) . . ? O2 C22 Re1 177.7(2) . . ? O3 C23 Re1 178.7(2) . . ? C1 C24 H24A 109.5 . . ? C1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C11 C25 H25A 109.5 . . ? C11 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C11 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O1S C1S C3S 121.9(3) . . ? O1S C1S C2S 121.6(3) . . ? C3S C1S C2S 116.6(3) . . ? C1S C2S H2SA 109.5 . . ? C1S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? C1S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? C1S C3S H3SA 109.5 . . ? C1S C3S H3SB 109.5 . . ? H3SA C3S H3SB 109.5 . . ? C1S C3S H3SC 109.5 . . ? H3SA C3S H3SC 109.5 . . ? H3SB C3S H3SC 109.5 . . ? 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 C21 Re1 N1 C1 -38.1(2) . . . . ? C22 Re1 N1 C1 87.7(11) . . . . ? C23 Re1 N1 C1 -126.7(2) . . . . ? N5 Re1 N1 C1 141.6(2) . . . . ? Br1 Re1 N1 C1 59.1(2) . . . . ? C21 Re1 N1 N2 147.82(19) . . . . ? C22 Re1 N1 N2 -86.3(11) . . . . ? C23 Re1 N1 N2 59.28(19) . . . . ? N5 Re1 N1 N2 -32.39(18) . . . . ? Br1 Re1 N1 N2 -114.96(17) . . . . ? C1 N1 N2 C3 -0.2(3) . . . . ? Re1 N1 N2 C3 175.26(16) . . . . ? C1 N1 N2 C4 171.8(2) . . . . ? Re1 N1 N2 C4 -12.8(3) . . . . ? C11 N3 N4 C13 0.1(3) . . . . ? C11 N3 N4 C14 -178.0(2) . . . . ? C21 Re1 N5 C19 -158.4(10) . . . . ? C22 Re1 N5 C19 15.44(19) . . . . ? C23 Re1 N5 C19 105.27(18) . . . . ? N1 Re1 N5 C19 -160.73(18) . . . . ? Br1 Re1 N5 C19 -72.88(17) . . . . ? C21 Re1 N5 C9 66.5(10) . . . . ? C22 Re1 N5 C9 -119.62(17) . . . . ? C23 Re1 N5 C9 -29.79(17) . . . . ? N1 Re1 N5 C9 64.21(16) . . . . ? Br1 Re1 N5 C9 152.06(16) . . . . ? N2 N1 C1 C2 0.1(3) . . . . ? Re1 N1 C1 C2 -174.67(17) . . . . ? N2 N1 C1 C24 -177.9(2) . . . . ? Re1 N1 C1 C24 7.3(4) . . . . ? N1 C1 C2 C3 0.0(3) . . . . ? C24 C1 C2 C3 177.9(3) . . . . ? N1 N2 C3 C2 0.2(3) . . . . ? C4 N2 C3 C2 -171.5(2) . . . . ? C1 C2 C3 N2 -0.1(3) . . . . ? C3 N2 C4 C5 34.1(4) . . . . ? N1 N2 C4 C5 -136.6(2) . . . . ? C3 N2 C4 C9 -143.3(3) . . . . ? N1 N2 C4 C9 46.0(3) . . . . ? C9 C4 C5 C6 1.9(4) . . . . ? N2 C4 C5 C6 -175.5(2) . . . . ? C4 C5 C6 C7 -1.8(4) . . . . ? C4 C5 C6 C10 177.6(2) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C10 C6 C7 C8 -179.3(2) . . . . ? C6 C7 C8 C9 1.4(4) . . . . ? C7 C8 C9 C4 -1.3(4) . . . . ? C7 C8 C9 N5 179.3(2) . . . . ? C5 C4 C9 C8 -0.4(4) . . . . ? N2 C4 C9 C8 176.9(2) . . . . ? C5 C4 C9 N5 179.1(2) . . . . ? N2 C4 C9 N5 -3.6(3) . . . . ? C19 N5 C9 C8 -15.0(3) . . . . ? Re1 N5 C9 C8 121.4(2) . . . . ? C19 N5 C9 C4 165.6(2) . . . . ? Re1 N5 C9 C4 -58.0(2) . . . . ? N4 N3 C11 C12 -0.1(3) . . . . ? N4 N3 C11 C25 179.8(2) . . . . ? N3 C11 C12 C13 0.1(3) . . . . ? C25 C11 C12 C13 -179.8(3) . . . . ? N3 N4 C13 C12 0.0(3) . . . . ? C14 N4 C13 C12 177.9(2) . . . . ? C11 C12 C13 N4 0.0(3) . . . . ? C13 N4 C14 C15 24.7(4) . . . . ? N3 N4 C14 C15 -157.7(2) . . . . ? C13 N4 C14 C19 -155.1(3) . . . . ? N3 N4 C14 C19 22.6(3) . . . . ? C19 C14 C15 C16 0.5(4) . . . . ? N4 C14 C15 C16 -179.2(2) . . . . ? C14 C15 C16 C17 0.5(4) . . . . ? C14 C15 C16 C20 -178.5(2) . . . . ? C15 C16 C17 C18 -0.5(4) . . . . ? C20 C16 C17 C18 178.4(2) . . . . ? C16 C17 C18 C19 -0.4(4) . . . . ? C17 C18 C19 C14 1.3(4) . . . . ? C17 C18 C19 N5 -177.9(2) . . . . ? C15 C14 C19 C18 -1.4(4) . . . . ? N4 C14 C19 C18 178.3(2) . . . . ? C15 C14 C19 N5 177.9(2) . . . . ? N4 C14 C19 N5 -2.4(4) . . . . ? C9 N5 C19 C18 71.5(3) . . . . ? Re1 N5 C19 C18 -61.2(3) . . . . ? C9 N5 C19 C14 -107.8(3) . . . . ? Re1 N5 C19 C14 119.5(2) . . . . ? C22 Re1 C21 O1 46(5) . . . . ? C23 Re1 C21 O1 -43(5) . . . . ? N1 Re1 C21 O1 -138(5) . . . . ? N5 Re1 C21 O1 -140(5) . . . . ? Br1 Re1 C21 O1 135(5) . . . . ? C21 Re1 C22 O2 8(5) . . . . ? C23 Re1 C22 O2 97(5) . . . . ? N1 Re1 C22 O2 -118(5) . . . . ? N5 Re1 C22 O2 -171(5) . . . . ? Br1 Re1 C22 O2 -89(5) . . . . ? C21 Re1 C23 O3 85(9) . . . . ? C22 Re1 C23 O3 -1(9) . . . . ? N1 Re1 C23 O3 -178(100) . . . . ? N5 Re1 C23 O3 -100(9) . . . . ? Br1 Re1 C23 O3 -81(10) . . . . ? 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 N5 H5N N3 0.80(3) 2.03(3) 2.698(3) 141(3) . _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.613 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.075 #===END data_gard8oa_1iPr _database_code_depnum_ccdc_archive 'CCDC 806480' #TrackingRef 'Re_Pincer_full.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H31 Br N5 O3 Re' _chemical_formula_weight 763.70 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 13.1679(2) _cell_length_b 13.4486(2) _cell_length_c 16.2017(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2869.16(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9735 _cell_measurement_theta_min 3 _cell_measurement_theta_max 67 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 10.234 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.3090 _exptl_absorpt_correction_T_max 0.4276 _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23851 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 68.17 _reflns_number_total 5079 _reflns_number_gt 5039 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _refine_special_details ; Racemic TWIN (26%) ; _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^)+(0.0316P)^2^+2.0540P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _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 0.257(5) _refine_ls_number_reflns 5079 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0170 _refine_ls_R_factor_gt 0.0168 _refine_ls_wR_factor_ref 0.0429 _refine_ls_wR_factor_gt 0.0428 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 Re1 Re 0.236988(9) 0.260299(8) 0.240135(7) 0.01175(4) Uani 1 1 d . . . Br1 Br 0.18141(2) 0.44522(2) 0.25997(2) 0.01911(7) Uani 1 1 d . . . O1 O 0.14480(17) 0.26169(19) 0.06610(13) 0.0250(5) Uani 1 1 d . . . O2 O 0.29769(15) 0.04609(18) 0.22755(15) 0.0206(5) Uani 1 1 d . . . O3 O 0.44335(18) 0.29458(18) 0.15775(15) 0.0241(5) Uani 1 1 d . . . N1 N 0.28953(18) 0.27019(19) 0.36862(14) 0.0141(5) Uani 1 1 d . . . N2 N 0.24686(19) 0.21272(18) 0.43034(15) 0.0155(5) Uani 1 1 d . . . N3 N 0.0164(2) 0.3550(2) 0.43270(16) 0.0169(5) Uani 1 1 d . . . N4 N -0.0516(2) 0.3817(2) 0.37259(17) 0.0147(6) Uani 1 1 d . . . N5 N 0.09253(19) 0.2329(2) 0.31226(15) 0.0131(5) Uani 1 1 d . . . H5N H 0.091(3) 0.268(3) 0.341(2) 0.016 Uiso 1 1 d . . . C1 C 0.3540(2) 0.3324(2) 0.4066(2) 0.0167(6) Uani 1 1 d . . . C2 C 0.3532(3) 0.3152(2) 0.4919(2) 0.0214(7) Uani 1 1 d . . . H2A H 0.3922 0.3487 0.5327 0.026 Uiso 1 1 calc R . . C3 C 0.2847(2) 0.2401(2) 0.50429(18) 0.0200(6) Uani 1 1 d . . . H3A H 0.2668 0.2121 0.5561 0.024 Uiso 1 1 calc R . . C4 C 0.1808(2) 0.1313(2) 0.41444(18) 0.0145(6) Uani 1 1 d . . . C5 C 0.1937(2) 0.0447(2) 0.46002(19) 0.0168(6) Uani 1 1 d . . . H5A H 0.2486 0.0401 0.4979 0.020 Uiso 1 1 calc R . . C6 C 0.1276(3) -0.0357(2) 0.4513(2) 0.0180(7) Uani 1 1 d . . . C7 C 0.0493(2) -0.0267(3) 0.3937(2) 0.0174(7) Uani 1 1 d . . . H7A H 0.0039 -0.0808 0.3860 0.021 Uiso 1 1 calc R . . C8 C 0.0361(2) 0.0592(2) 0.34756(19) 0.0165(6) Uani 1 1 d . . . H8A H -0.0177 0.0630 0.3086 0.020 Uiso 1 1 calc R . . C9 C 0.1008(2) 0.1395(2) 0.35780(19) 0.0143(6) Uani 1 1 d . . . C10 C 0.1392(3) -0.1265(2) 0.5040(2) 0.0237(7) Uani 1 1 d . . . H10A H 0.0840 -0.1732 0.4920 0.036 Uiso 1 1 calc R . . H10B H 0.1366 -0.1075 0.5624 0.036 Uiso 1 1 calc R . . H10C H 0.2046 -0.1583 0.4922 0.036 Uiso 1 1 calc R . . C11 C 0.0191(2) 0.4305(2) 0.4847(2) 0.0179(6) Uani 1 1 d . . . C12 C -0.0465(3) 0.5073(2) 0.4593(2) 0.0196(7) Uani 1 1 d . . . H12A H -0.0583 0.5690 0.4864 0.023 Uiso 1 1 calc R . . C13 C -0.0899(3) 0.4743(2) 0.3871(2) 0.0168(7) Uani 1 1 d . . . H13A H -0.1374 0.5092 0.3538 0.020 Uiso 1 1 calc R . . C14 C -0.0753(2) 0.3186(2) 0.30527(19) 0.0139(6) Uani 1 1 d . . . C15 C -0.1712(2) 0.3275(2) 0.2687(2) 0.0173(6) Uani 1 1 d . . . H15A H -0.2186 0.3736 0.2909 0.021 Uiso 1 1 calc R . . C16 C -0.1985(2) 0.2710(2) 0.20112(18) 0.0167(6) Uani 1 1 d . . . C17 C -0.1283(2) 0.2040(2) 0.16867(19) 0.0170(6) Uani 1 1 d . . . H17A H -0.1455 0.1651 0.1218 0.020 Uiso 1 1 calc R . . C18 C -0.0337(2) 0.1943(2) 0.20479(19) 0.0157(6) Uani 1 1 d . . . H18A H 0.0137 0.1487 0.1818 0.019 Uiso 1 1 calc R . . C19 C -0.0061(2) 0.2489(2) 0.27351(17) 0.0135(5) Uani 1 1 d . . . C20 C -0.3042(3) 0.2805(3) 0.1650(2) 0.0260(8) Uani 1 1 d . . . H20A H -0.3225 0.3510 0.1610 0.039 Uiso 1 1 calc R . . H20B H -0.3530 0.2462 0.2007 0.039 Uiso 1 1 calc R . . H20C H -0.3055 0.2506 0.1098 0.039 Uiso 1 1 calc R . . C21 C 0.1785(2) 0.2599(3) 0.13064(18) 0.0174(6) Uani 1 1 d . . . C22 C 0.2739(2) 0.1204(3) 0.23235(18) 0.0208(7) Uani 1 1 d . . . C23 C 0.3671(2) 0.2849(2) 0.1890(2) 0.0163(6) Uani 1 1 d . . . C24 C 0.4212(3) 0.4047(2) 0.3608(2) 0.0212(7) Uani 1 1 d . . . H24A H 0.3994 0.4058 0.3017 0.025 Uiso 1 1 calc R . . C25 C 0.5308(3) 0.3672(3) 0.3644(3) 0.0288(9) Uani 1 1 d . . . H25A H 0.5354 0.3026 0.3367 0.043 Uiso 1 1 calc R . . H25B H 0.5517 0.3602 0.4221 0.043 Uiso 1 1 calc R . . H25C H 0.5754 0.4149 0.3366 0.043 Uiso 1 1 calc R . . C26 C 0.4112(3) 0.5097(3) 0.3952(2) 0.0282(8) Uani 1 1 d . . . H26A H 0.3401 0.5308 0.3922 0.042 Uiso 1 1 calc R . . H26B H 0.4533 0.5552 0.3626 0.042 Uiso 1 1 calc R . . H26C H 0.4338 0.5105 0.4528 0.042 Uiso 1 1 calc R . . C27 C 0.0879(3) 0.4286(3) 0.5588(2) 0.0250(8) Uani 1 1 d . . . H27A H 0.1216 0.3620 0.5608 0.030 Uiso 1 1 calc R . . C28 C 0.0277(3) 0.4421(3) 0.6394(2) 0.0346(9) Uani 1 1 d . . . H28A H -0.0249 0.3907 0.6432 0.052 Uiso 1 1 calc R . . H28B H -0.0042 0.5079 0.6399 0.052 Uiso 1 1 calc R . . H28C H 0.0739 0.4362 0.6866 0.052 Uiso 1 1 calc R . . C29 C 0.1712(3) 0.5080(3) 0.5492(2) 0.0331(9) Uani 1 1 d . . . H29A H 0.2101 0.4951 0.4988 0.050 Uiso 1 1 calc R . . H29B H 0.2168 0.5055 0.5970 0.050 Uiso 1 1 calc R . . H29C H 0.1399 0.5740 0.5458 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.01065(6) 0.01247(6) 0.01213(6) -0.00015(4) -0.00029(4) 0.00052(4) Br1 0.01933(14) 0.01633(14) 0.02168(16) 0.00153(14) 0.00012(14) 0.00178(10) O1 0.0256(12) 0.0347(14) 0.0147(11) 0.0001(11) -0.0026(8) 0.0044(12) O2 0.0090(10) 0.0277(13) 0.0250(12) 0.0085(11) -0.0012(9) -0.0005(9) O3 0.0180(12) 0.0257(13) 0.0285(13) -0.0007(10) 0.0052(10) -0.0023(10) N1 0.0134(12) 0.0183(12) 0.0105(11) 0.0019(10) -0.0021(9) -0.0012(10) N2 0.0127(13) 0.0186(12) 0.0152(12) 0.0019(9) -0.0018(10) 0.0002(10) N3 0.0141(13) 0.0195(13) 0.0170(14) 0.0009(11) -0.0026(10) 0.0002(11) N4 0.0117(13) 0.0170(13) 0.0154(13) 0.0005(11) 0.0014(10) 0.0002(10) N5 0.0136(12) 0.0134(13) 0.0124(12) -0.0009(11) -0.0005(10) -0.0006(11) C1 0.0140(15) 0.0148(15) 0.0215(17) -0.0003(12) -0.0018(12) 0.0004(12) C2 0.0192(17) 0.0233(16) 0.0218(17) -0.0014(14) -0.0066(13) -0.0022(14) C3 0.0199(15) 0.0240(16) 0.0161(13) 0.0008(13) -0.0053(11) -0.0003(14) C4 0.0146(15) 0.0157(15) 0.0132(14) -0.0007(12) 0.0013(12) 0.0005(11) C5 0.0166(15) 0.0211(16) 0.0128(14) 0.0013(13) -0.0010(12) 0.0055(12) C6 0.0229(17) 0.0158(16) 0.0154(15) 0.0004(13) 0.0048(13) 0.0026(13) C7 0.0142(16) 0.0174(16) 0.0207(16) -0.0012(13) 0.0013(13) -0.0013(14) C8 0.0143(15) 0.0179(16) 0.0174(15) -0.0018(13) -0.0018(12) 0.0004(12) C9 0.0144(15) 0.0165(15) 0.0119(14) 0.0001(12) 0.0027(12) 0.0035(12) C10 0.0306(19) 0.0175(16) 0.0232(17) 0.0041(14) -0.0002(14) 0.0025(14) C11 0.0176(16) 0.0194(16) 0.0167(15) -0.0012(13) 0.0043(12) -0.0026(12) C12 0.0208(17) 0.0168(16) 0.0212(16) -0.0040(13) 0.0044(13) -0.0001(13) C13 0.0148(16) 0.0133(15) 0.0222(16) 0.0011(13) 0.0015(13) 0.0021(13) C14 0.0139(15) 0.0147(14) 0.0133(14) 0.0032(12) -0.0002(11) -0.0018(12) C15 0.0151(14) 0.0160(14) 0.0208(16) 0.0038(13) 0.0028(13) 0.0021(11) C16 0.0151(14) 0.0183(15) 0.0165(14) 0.0037(13) -0.0011(10) -0.0011(12) C17 0.0205(16) 0.0159(15) 0.0145(15) 0.0014(12) -0.0025(12) -0.0049(12) C18 0.0132(15) 0.0157(15) 0.0182(15) 0.0009(12) 0.0030(12) 0.0007(12) C19 0.0123(12) 0.0133(13) 0.0147(13) 0.0034(13) -0.0007(9) -0.0019(11) C20 0.0186(16) 0.034(2) 0.0257(17) 0.0003(15) -0.0051(13) 0.0033(14) C21 0.0145(14) 0.0200(16) 0.0179(15) -0.0014(14) 0.0036(11) 0.0007(13) C22 0.0115(14) 0.041(2) 0.0098(14) -0.0065(13) 0.0015(12) -0.0154(13) C23 0.0160(16) 0.0149(15) 0.0180(15) 0.0007(12) 0.0017(12) -0.0039(12) C24 0.0190(17) 0.0200(16) 0.0245(17) 0.0009(14) -0.0024(13) -0.0046(14) C25 0.0157(18) 0.027(2) 0.044(2) 0.0000(18) 0.0007(15) -0.0062(14) C26 0.0297(19) 0.0227(18) 0.032(2) 0.0012(16) -0.0052(16) -0.0080(16) C27 0.0284(19) 0.0276(19) 0.0190(17) -0.0054(15) -0.0048(14) 0.0046(15) C28 0.053(3) 0.032(2) 0.0191(18) -0.0047(17) 0.0015(17) 0.003(2) C29 0.032(2) 0.040(2) 0.0274(19) -0.0117(18) -0.0045(16) -0.0019(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C23 1.932(3) . ? Re1 C21 1.934(3) . ? Re1 C22 1.947(4) . ? Re1 N1 2.198(2) . ? Re1 N5 2.263(3) . ? Re1 Br1 2.6123(3) . ? O1 C21 1.136(4) . ? O2 C22 1.050(4) . ? O3 C23 1.132(4) . ? N1 C1 1.341(4) . ? N1 N2 1.383(4) . ? N2 C3 1.349(4) . ? N2 C4 1.422(4) . ? N3 C11 1.320(4) . ? N3 N4 1.371(4) . ? N4 C13 1.364(4) . ? N4 C14 1.417(4) . ? N5 C19 1.458(4) . ? N5 C9 1.460(4) . ? N5 H5N 0.66(4) . ? C1 C2 1.401(5) . ? C1 C24 1.509(4) . ? C2 C3 1.370(5) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C5 1.389(4) . ? C4 C9 1.402(4) . ? C5 C6 1.395(5) . ? C5 H5A 0.9500 . ? C6 C7 1.395(5) . ? C6 C10 1.499(5) . ? C7 C8 1.387(5) . ? C7 H7A 0.9500 . ? C8 C9 1.386(5) . ? C8 H8A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.408(5) . ? C11 C27 1.504(5) . ? C12 C13 1.376(5) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.400(4) . ? C14 C19 1.405(4) . ? C15 C16 1.381(4) . ? C15 H15A 0.9500 . ? C16 C17 1.393(5) . ? C16 C20 1.516(4) . ? C17 C18 1.383(5) . ? C17 H17A 0.9500 . ? C18 C19 1.383(4) . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C24 C26 1.524(5) . ? C24 C25 1.529(5) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.538(5) . ? C27 C29 1.540(5) . ? C27 H27A 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? 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 C23 Re1 C21 87.70(13) . . ? C23 Re1 C22 85.20(13) . . ? C21 Re1 C22 92.12(13) . . ? C23 Re1 N1 96.71(11) . . ? C21 Re1 N1 173.96(11) . . ? C22 Re1 N1 92.36(11) . . ? C23 Re1 N5 174.32(12) . . ? C21 Re1 N5 97.97(11) . . ? C22 Re1 N5 94.93(11) . . ? N1 Re1 N5 77.61(9) . . ? C23 Re1 Br1 97.94(9) . . ? C21 Re1 Br1 90.24(10) . . ? C22 Re1 Br1 176.15(9) . . ? N1 Re1 Br1 85.07(7) . . ? N5 Re1 Br1 81.72(7) . . ? C1 N1 N2 105.9(2) . . ? C1 N1 Re1 132.2(2) . . ? N2 N1 Re1 121.54(18) . . ? C3 N2 N1 109.9(2) . . ? C3 N2 C4 126.6(3) . . ? N1 N2 C4 123.2(2) . . ? C11 N3 N4 105.6(3) . . ? C13 N4 N3 111.0(3) . . ? C13 N4 C14 126.7(3) . . ? N3 N4 C14 122.2(3) . . ? C19 N5 C9 114.3(2) . . ? C19 N5 Re1 120.13(18) . . ? C9 N5 Re1 109.78(18) . . ? C19 N5 H5N 100(4) . . ? C9 N5 H5N 105(4) . . ? Re1 N5 H5N 106(4) . . ? N1 C1 C2 110.2(3) . . ? N1 C1 C24 123.2(3) . . ? C2 C1 C24 126.5(3) . . ? C3 C2 C1 105.7(3) . . ? C3 C2 H2A 127.1 . . ? C1 C2 H2A 127.1 . . ? N2 C3 C2 108.3(3) . . ? N2 C3 H3A 125.8 . . ? C2 C3 H3A 125.8 . . ? C5 C4 C9 120.4(3) . . ? C5 C4 N2 118.4(3) . . ? C9 C4 N2 121.1(3) . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C5 C6 C7 117.5(3) . . ? C5 C6 C10 120.6(3) . . ? C7 C6 C10 121.8(3) . . ? C8 C7 C6 121.7(3) . . ? C8 C7 H7A 119.2 . . ? C6 C7 H7A 119.2 . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 C4 118.6(3) . . ? C8 C9 N5 124.3(3) . . ? C4 C9 N5 117.1(3) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 111.2(3) . . ? N3 C11 C27 120.9(3) . . ? C12 C11 C27 127.9(3) . . ? C13 C12 C11 105.4(3) . . ? C13 C12 H12A 127.3 . . ? C11 C12 H12A 127.3 . . ? N4 C13 C12 106.7(3) . . ? N4 C13 H13A 126.6 . . ? C12 C13 H13A 126.6 . . ? C15 C14 C19 119.2(3) . . ? C15 C14 N4 118.2(3) . . ? C19 C14 N4 122.6(3) . . ? C16 C15 C14 121.5(3) . . ? C16 C15 H15A 119.2 . . ? C14 C15 H15A 119.2 . . ? C15 C16 C17 118.9(3) . . ? C15 C16 C20 119.9(3) . . ? C17 C16 C20 121.2(3) . . ? C18 C17 C16 120.0(3) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C19 C18 C17 121.8(3) . . ? C19 C18 H18A 119.1 . . ? C17 C18 H18A 119.1 . . ? C18 C19 C14 118.6(3) . . ? C18 C19 N5 120.1(3) . . ? C14 C19 N5 121.3(3) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 Re1 178.5(3) . . ? O2 C22 Re1 177.0(3) . . ? O3 C23 Re1 176.6(3) . . ? C1 C24 C26 111.5(3) . . ? C1 C24 C25 108.9(3) . . ? C26 C24 C25 111.9(3) . . ? C1 C24 H24A 108.2 . . ? C26 C24 H24A 108.2 . . ? C25 C24 H24A 108.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C11 C27 C28 111.5(3) . . ? C11 C27 C29 109.6(3) . . ? C28 C27 C29 111.8(3) . . ? C11 C27 H27A 107.9 . . ? C28 C27 H27A 107.9 . . ? C29 C27 H27A 107.9 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? 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 C23 Re1 N1 C1 41.7(3) . . . . ? C21 Re1 N1 C1 -95.0(12) . . . . ? C22 Re1 N1 C1 127.2(3) . . . . ? N5 Re1 N1 C1 -138.3(3) . . . . ? Br1 Re1 N1 C1 -55.7(3) . . . . ? C23 Re1 N1 N2 -146.4(2) . . . . ? C21 Re1 N1 N2 76.9(12) . . . . ? C22 Re1 N1 N2 -61.0(2) . . . . ? N5 Re1 N1 N2 33.6(2) . . . . ? Br1 Re1 N1 N2 116.1(2) . . . . ? C1 N1 N2 C3 0.2(3) . . . . ? Re1 N1 N2 C3 -173.5(2) . . . . ? C1 N1 N2 C4 -174.2(3) . . . . ? Re1 N1 N2 C4 12.0(4) . . . . ? C11 N3 N4 C13 0.7(3) . . . . ? C11 N3 N4 C14 -179.8(3) . . . . ? C23 Re1 N5 C19 159.0(11) . . . . ? C21 Re1 N5 C19 -17.1(2) . . . . ? C22 Re1 N5 C19 -110.0(2) . . . . ? N1 Re1 N5 C19 158.7(2) . . . . ? Br1 Re1 N5 C19 72.0(2) . . . . ? C23 Re1 N5 C9 -65.5(12) . . . . ? C21 Re1 N5 C9 118.4(2) . . . . ? C22 Re1 N5 C9 25.6(2) . . . . ? N1 Re1 N5 C9 -65.76(19) . . . . ? Br1 Re1 N5 C9 -152.49(19) . . . . ? N2 N1 C1 C2 0.2(3) . . . . ? Re1 N1 C1 C2 173.0(2) . . . . ? N2 N1 C1 C24 176.4(3) . . . . ? Re1 N1 C1 C24 -10.8(5) . . . . ? N1 C1 C2 C3 -0.5(4) . . . . ? C24 C1 C2 C3 -176.6(3) . . . . ? N1 N2 C3 C2 -0.5(4) . . . . ? C4 N2 C3 C2 173.6(3) . . . . ? C1 C2 C3 N2 0.6(4) . . . . ? C3 N2 C4 C5 -35.9(4) . . . . ? N1 N2 C4 C5 137.5(3) . . . . ? C3 N2 C4 C9 140.3(3) . . . . ? N1 N2 C4 C9 -46.2(4) . . . . ? C9 C4 C5 C6 -0.4(5) . . . . ? N2 C4 C5 C6 175.9(3) . . . . ? C4 C5 C6 C7 1.3(5) . . . . ? C4 C5 C6 C10 -176.8(3) . . . . ? C5 C6 C7 C8 -1.0(5) . . . . ? C10 C6 C7 C8 177.1(3) . . . . ? C6 C7 C8 C9 -0.3(5) . . . . ? C7 C8 C9 C4 1.3(5) . . . . ? C7 C8 C9 N5 -179.8(3) . . . . ? C5 C4 C9 C8 -0.9(4) . . . . ? N2 C4 C9 C8 -177.1(3) . . . . ? C5 C4 C9 N5 -179.9(3) . . . . ? N2 C4 C9 N5 3.9(4) . . . . ? C19 N5 C9 C8 18.1(4) . . . . ? Re1 N5 C9 C8 -120.2(3) . . . . ? C19 N5 C9 C4 -162.9(3) . . . . ? Re1 N5 C9 C4 58.7(3) . . . . ? N4 N3 C11 C12 -0.1(4) . . . . ? N4 N3 C11 C27 -178.9(3) . . . . ? N3 C11 C12 C13 -0.4(4) . . . . ? C27 C11 C12 C13 178.3(3) . . . . ? N3 N4 C13 C12 -0.9(4) . . . . ? C14 N4 C13 C12 179.6(3) . . . . ? C11 C12 C13 N4 0.8(4) . . . . ? C13 N4 C14 C15 -28.2(5) . . . . ? N3 N4 C14 C15 152.3(3) . . . . ? C13 N4 C14 C19 150.9(3) . . . . ? N3 N4 C14 C19 -28.6(4) . . . . ? C19 C14 C15 C16 -1.3(4) . . . . ? N4 C14 C15 C16 177.8(3) . . . . ? C14 C15 C16 C17 -0.4(5) . . . . ? C14 C15 C16 C20 178.1(3) . . . . ? C15 C16 C17 C18 0.8(5) . . . . ? C20 C16 C17 C18 -177.6(3) . . . . ? C16 C17 C18 C19 0.5(5) . . . . ? C17 C18 C19 C14 -2.2(4) . . . . ? C17 C18 C19 N5 176.9(3) . . . . ? C15 C14 C19 C18 2.6(4) . . . . ? N4 C14 C19 C18 -176.5(3) . . . . ? C15 C14 C19 N5 -176.5(3) . . . . ? N4 C14 C19 N5 4.4(4) . . . . ? C9 N5 C19 C18 -72.5(3) . . . . ? Re1 N5 C19 C18 61.2(3) . . . . ? C9 N5 C19 C14 106.6(3) . . . . ? Re1 N5 C19 C14 -119.7(3) . . . . ? C23 Re1 C21 O1 -63(11) . . . . ? C22 Re1 C21 O1 -148(11) . . . . ? N1 Re1 C21 O1 74(11) . . . . ? N5 Re1 C21 O1 117(11) . . . . ? Br1 Re1 C21 O1 35(11) . . . . ? C23 Re1 C22 O2 15(6) . . . . ? C21 Re1 C22 O2 102(6) . . . . ? N1 Re1 C22 O2 -82(6) . . . . ? N5 Re1 C22 O2 -160(6) . . . . ? Br1 Re1 C22 O2 -130(5) . . . . ? C21 Re1 C23 O3 -74(5) . . . . ? C22 Re1 C23 O3 18(5) . . . . ? N1 Re1 C23 O3 110(5) . . . . ? N5 Re1 C23 O3 110(5) . . . . ? Br1 Re1 C23 O3 -164(5) . . . . ? N1 C1 C24 C26 129.1(3) . . . . ? C2 C1 C24 C26 -55.3(5) . . . . ? N1 C1 C24 C25 -107.0(4) . . . . ? C2 C1 C24 C25 68.6(4) . . . . ? N3 C11 C27 C28 -122.6(4) . . . . ? C12 C11 C27 C28 58.8(5) . . . . ? N3 C11 C27 C29 113.1(4) . . . . ? C12 C11 C27 C29 -65.5(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 N5 H5N N3 0.66(4) 2.13(4) 2.740(4) 154(5) . _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 68.17 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.642 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.078 #===END data_gard8ka_2Me _database_code_depnum_ccdc_archive 'CCDC 806481' #TrackingRef 'Re_Pincer_full.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H23 F6 N5 O3 P Re' _chemical_formula_weight 772.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -5.2083 5.8923 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.63640(10) _cell_length_b 9.66670(10) _cell_length_c 16.7540(2) _cell_angle_alpha 78.9030(10) _cell_angle_beta 82.4590(10) _cell_angle_gamma 78.8010(10) _cell_volume 1340.01(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8854 _cell_measurement_theta_min 3 _cell_measurement_theta_max 67 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.915 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 10.165 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.1775 _exptl_absorpt_correction_T_max 0.4297 _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11073 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 67.70 _reflns_number_total 4556 _reflns_number_gt 4473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+1.8741P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4556 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0194 _refine_ls_R_factor_gt 0.0188 _refine_ls_wR_factor_ref 0.0478 _refine_ls_wR_factor_gt 0.0474 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.406675(13) -0.221455(11) 0.266028(7) 0.01258(5) Uani 1 1 d . . . O1 O 0.6767(3) -0.3340(2) 0.37693(14) 0.0277(5) Uani 1 1 d . . . O2 O 0.6781(2) -0.1889(2) 0.12895(13) 0.0227(4) Uani 1 1 d . . . O3 O 0.4264(3) -0.5180(2) 0.22196(13) 0.0236(4) Uani 1 1 d . . . N1 N 0.2207(3) -0.2411(2) 0.36694(13) 0.0145(4) Uani 1 1 d . . . N2 N 0.1038(3) -0.1320(2) 0.38835(14) 0.0169(5) Uani 1 1 d . . . N3 N 0.2208(3) -0.1156(2) 0.18795(13) 0.0139(4) Uani 1 1 d . . . N4 N 0.2284(3) 0.0168(2) 0.14158(14) 0.0167(5) Uani 1 1 d . . . N5 N 0.3683(3) 0.0070(2) 0.28583(14) 0.0153(5) Uani 1 1 d . . . H5N H 0.426(5) 0.005(4) 0.324(3) 0.035(11) Uiso 1 1 d . . . C1 C 0.1982(3) -0.3577(3) 0.42359(17) 0.0187(6) Uani 1 1 d . . . C2 C 0.0701(4) -0.3220(3) 0.48005(18) 0.0222(6) Uani 1 1 d . . . H2A H 0.0301 -0.3842 0.5258 0.027 Uiso 1 1 calc R . . C3 C 0.0137(4) -0.1802(3) 0.45653(18) 0.0216(6) Uani 1 1 d . . . H3A H -0.0736 -0.1248 0.4833 0.026 Uiso 1 1 calc R . . C4 C 0.0839(3) 0.0139(3) 0.34734(16) 0.0162(5) Uani 1 1 d . . . C5 C -0.0700(3) 0.0927(3) 0.35586(18) 0.0196(6) Uani 1 1 d . . . H5A H -0.1541 0.0444 0.3814 0.024 Uiso 1 1 calc R . . C6 C -0.1028(4) 0.2381(3) 0.32830(19) 0.0225(6) Uani 1 1 d . . . C7 C 0.0215(4) 0.3066(3) 0.29086(19) 0.0256(7) Uani 1 1 d . . . H7A H 0.0021 0.4072 0.2727 0.031 Uiso 1 1 calc R . . C8 C 0.1729(4) 0.2304(3) 0.27972(19) 0.0227(6) Uani 1 1 d . . . H8A H 0.2561 0.2793 0.2533 0.027 Uiso 1 1 calc R . . C9 C 0.2064(3) 0.0824(3) 0.30653(17) 0.0167(5) Uani 1 1 d . . . C10 C -0.2687(4) 0.3214(3) 0.3399(2) 0.0289(7) Uani 1 1 d . . . H10A H -0.3416 0.2553 0.3643 0.043 Uiso 1 1 calc R . . H10B H -0.3017 0.3728 0.2868 0.043 Uiso 1 1 calc R . . H10C H -0.2705 0.3902 0.3762 0.043 Uiso 1 1 calc R . . C11 C 0.0832(3) -0.1489(3) 0.17449(17) 0.0175(6) Uani 1 1 d . . . C12 C 0.0046(4) -0.0385(3) 0.11978(19) 0.0236(6) Uani 1 1 d . . . H12A H -0.0944 -0.0352 0.0999 0.028 Uiso 1 1 calc R . . C13 C 0.0992(4) 0.0644(3) 0.10045(18) 0.0220(6) Uani 1 1 d . . . H13A H 0.0774 0.1532 0.0645 0.026 Uiso 1 1 calc R . . C14 C 0.3628(3) 0.0849(3) 0.13741(17) 0.0166(5) Uani 1 1 d . . . C15 C 0.4181(4) 0.1587(3) 0.06375(17) 0.0197(6) Uani 1 1 d . . . H15A H 0.3673 0.1627 0.0162 0.024 Uiso 1 1 calc R . . C16 C 0.5476(4) 0.2278(3) 0.05808(18) 0.0214(6) Uani 1 1 d . . . C17 C 0.6242(3) 0.2153(3) 0.12776(19) 0.0218(6) Uani 1 1 d . . . H17A H 0.7159 0.2577 0.1244 0.026 Uiso 1 1 calc R . . C18 C 0.5684(3) 0.1416(3) 0.20237(18) 0.0196(6) Uani 1 1 d . . . H18A H 0.6216 0.1343 0.2495 0.023 Uiso 1 1 calc R . . C19 C 0.4358(3) 0.0789(3) 0.20801(17) 0.0166(5) Uani 1 1 d . . . C20 C 0.6010(4) 0.3128(4) -0.0225(2) 0.0312(7) Uani 1 1 d . . . H20A H 0.5082 0.3704 -0.0481 0.047 Uiso 1 1 calc R . . H20B H 0.6591 0.2474 -0.0585 0.047 Uiso 1 1 calc R . . H20C H 0.6705 0.3761 -0.0134 0.047 Uiso 1 1 calc R . . C21 C 0.5727(4) -0.2934(3) 0.33744(17) 0.0192(6) Uani 1 1 d . . . C22 C 0.5745(3) -0.1989(3) 0.17901(18) 0.0179(6) Uani 1 1 d . . . C23 C 0.4196(3) -0.4091(3) 0.24037(17) 0.0172(6) Uani 1 1 d . . . C24 C 0.2993(4) -0.5018(3) 0.42299(19) 0.0265(7) Uani 1 1 d . . . H24A H 0.4114 -0.4926 0.4177 0.040 Uiso 1 1 calc R . . H24B H 0.2782 -0.5416 0.3768 0.040 Uiso 1 1 calc R . . H24C H 0.2747 -0.5656 0.4741 0.040 Uiso 1 1 calc R . . C25 C 0.0321(4) -0.2874(3) 0.2137(2) 0.0242(6) Uani 1 1 d . . . H25A H -0.0075 -0.2834 0.2710 0.036 Uiso 1 1 calc R . . H25B H 0.1226 -0.3658 0.2112 0.036 Uiso 1 1 calc R . . H25C H -0.0524 -0.3038 0.1848 0.036 Uiso 1 1 calc R . . P1 P 0.5000 1.0000 0.5000 0.0191(2) Uani 1 2 d S . . F1 F 0.4115(2) 1.0185(2) 0.58938(11) 0.0296(4) Uani 1 1 d . . . F2 F 0.3594(2) 0.9284(2) 0.48214(12) 0.0377(5) Uani 1 1 d . . . F3 F 0.4085(3) 1.1522(2) 0.46182(13) 0.0433(5) Uani 1 1 d . . . P2 P 1.0000 0.5000 0.0000 0.0286(3) Uani 1 2 d S . . F4 F 0.9897(3) 0.3495(2) -0.02448(14) 0.0428(5) Uani 1 1 d . . . F5 F 1.1244(4) 0.4225(3) 0.0629(2) 0.0722(9) Uani 1 1 d . . . F6 F 1.1391(4) 0.5214(3) -0.06962(19) 0.0771(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.01354(7) 0.01053(7) 0.01362(7) -0.00137(4) -0.00379(5) -0.00098(4) O1 0.0281(12) 0.0244(11) 0.0311(12) -0.0027(9) -0.0186(10) 0.0029(9) O2 0.0170(10) 0.0276(11) 0.0237(11) -0.0049(8) 0.0015(10) -0.0059(8) O3 0.0291(11) 0.0137(10) 0.0290(11) -0.0064(8) -0.0049(9) -0.0019(8) N1 0.0164(11) 0.0127(11) 0.0132(11) -0.0015(8) 0.0000(9) -0.0018(9) N2 0.0181(11) 0.0132(11) 0.0186(11) -0.0026(9) -0.0006(10) -0.0013(9) N3 0.0153(11) 0.0115(11) 0.0141(11) 0.0004(8) -0.0032(9) -0.0015(9) N4 0.0195(12) 0.0138(11) 0.0172(11) 0.0007(9) -0.0056(10) -0.0044(9) N5 0.0186(12) 0.0125(11) 0.0159(11) -0.0020(9) -0.0032(10) -0.0048(9) C1 0.0237(14) 0.0160(14) 0.0166(13) -0.0001(11) -0.0057(12) -0.0042(11) C2 0.0288(16) 0.0188(14) 0.0189(14) 0.0007(11) -0.0001(13) -0.0090(12) C3 0.0217(14) 0.0213(15) 0.0216(14) -0.0042(12) 0.0027(12) -0.0059(12) C4 0.0207(14) 0.0139(13) 0.0153(13) -0.0037(10) -0.0051(11) -0.0025(11) C5 0.0179(14) 0.0205(15) 0.0214(14) -0.0057(11) -0.0021(12) -0.0036(11) C6 0.0236(15) 0.0195(15) 0.0253(15) -0.0081(12) -0.0074(13) 0.0020(12) C7 0.0337(17) 0.0127(14) 0.0279(16) -0.0033(12) -0.0023(14) 0.0014(12) C8 0.0271(16) 0.0146(14) 0.0260(15) -0.0034(11) 0.0010(13) -0.0050(12) C9 0.0199(14) 0.0141(13) 0.0166(13) -0.0045(10) -0.0035(11) -0.0014(11) C10 0.0266(16) 0.0211(16) 0.0396(18) -0.0094(13) -0.0095(14) 0.0027(13) C11 0.0159(13) 0.0165(14) 0.0212(14) -0.0018(11) -0.0052(12) -0.0045(11) C12 0.0205(14) 0.0222(15) 0.0290(16) 0.0016(12) -0.0122(13) -0.0049(12) C13 0.0243(15) 0.0171(14) 0.0242(15) 0.0032(11) -0.0103(13) -0.0035(11) C14 0.0189(13) 0.0129(13) 0.0183(13) -0.0029(10) -0.0020(11) -0.0034(10) C15 0.0249(15) 0.0169(14) 0.0174(13) -0.0025(11) -0.0028(12) -0.0041(11) C16 0.0251(15) 0.0165(14) 0.0217(15) -0.0037(11) 0.0055(13) -0.0063(12) C17 0.0203(14) 0.0193(14) 0.0277(15) -0.0073(12) 0.0015(13) -0.0078(11) C18 0.0203(14) 0.0195(14) 0.0210(14) -0.0066(11) -0.0036(12) -0.0045(11) C19 0.0206(14) 0.0111(13) 0.0174(13) -0.0018(10) -0.0031(11) -0.0013(10) C20 0.0396(19) 0.0326(18) 0.0233(16) -0.0028(13) 0.0057(15) -0.0188(15) C21 0.0243(15) 0.0137(13) 0.0189(14) -0.0030(11) -0.0011(13) -0.0017(11) C22 0.0192(14) 0.0148(14) 0.0206(14) -0.0036(11) -0.0081(13) -0.0006(11) C23 0.0163(13) 0.0161(15) 0.0177(13) -0.0008(11) -0.0041(11) 0.0002(10) C24 0.0324(17) 0.0175(15) 0.0240(15) 0.0045(12) -0.0007(14) -0.0001(12) C25 0.0236(15) 0.0191(15) 0.0306(16) 0.0049(12) -0.0104(13) -0.0096(12) P1 0.0171(5) 0.0248(5) 0.0171(5) -0.0053(4) -0.0046(4) -0.0036(4) F1 0.0261(9) 0.0453(11) 0.0218(9) -0.0121(8) -0.0014(8) -0.0112(8) F2 0.0344(11) 0.0599(14) 0.0294(10) -0.0171(9) -0.0013(9) -0.0261(10) F3 0.0475(12) 0.0325(11) 0.0418(12) 0.0010(9) -0.0085(10) 0.0080(9) P2 0.0315(6) 0.0155(5) 0.0386(6) 0.0045(5) -0.0133(5) -0.0055(4) F4 0.0587(14) 0.0203(10) 0.0522(13) 0.0005(9) -0.0236(11) -0.0083(9) F5 0.093(2) 0.0295(12) 0.102(2) 0.0005(13) -0.0736(19) 0.0009(13) F6 0.082(2) 0.081(2) 0.081(2) -0.0308(17) 0.0274(17) -0.0508(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C23 1.922(3) . ? Re1 C21 1.927(3) . ? Re1 C22 1.929(3) . ? Re1 N3 2.175(2) . ? Re1 N1 2.181(2) . ? Re1 N5 2.251(2) . ? O1 C21 1.148(4) . ? O2 C22 1.148(4) . ? O3 C23 1.141(4) . ? N1 C1 1.354(4) . ? N1 N2 1.378(3) . ? N2 C3 1.353(4) . ? N2 C4 1.433(4) . ? N3 C11 1.347(4) . ? N3 N4 1.372(3) . ? N4 C13 1.347(4) . ? N4 C14 1.429(4) . ? N5 C19 1.460(4) . ? N5 C9 1.477(4) . ? N5 H5N 0.86(4) . ? C1 C2 1.393(4) . ? C1 C24 1.494(4) . ? C2 C3 1.362(4) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C9 1.390(4) . ? C4 C5 1.402(4) . ? C5 C6 1.378(4) . ? C5 H5A 0.9500 . ? C6 C7 1.387(5) . ? C6 C10 1.509(4) . ? C7 C8 1.379(4) . ? C7 H7A 0.9500 . ? C8 C9 1.400(4) . ? C8 H8A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.395(4) . ? C11 C25 1.494(4) . ? C12 C13 1.373(4) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.378(4) . ? C14 C19 1.398(4) . ? C15 C16 1.394(4) . ? C15 H15A 0.9500 . ? C16 C17 1.390(4) . ? C16 C20 1.506(4) . ? C17 C18 1.391(4) . ? C17 H17A 0.9500 . ? C18 C19 1.381(4) . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? P1 F3 1.586(2) 2_676 ? P1 F3 1.586(2) . ? P1 F2 1.5951(18) 2_676 ? P1 F2 1.5951(18) . ? P1 F1 1.6148(17) . ? P1 F1 1.6148(17) 2_676 ? P2 F6 1.576(3) . ? P2 F6 1.576(3) 2_765 ? P2 F5 1.582(2) 2_765 ? P2 F5 1.582(2) . ? P2 F4 1.607(2) 2_765 ? P2 F4 1.607(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 C23 Re1 C21 90.56(11) . . ? C23 Re1 C22 85.73(12) . . ? C21 Re1 C22 86.20(12) . . ? C23 Re1 N3 96.07(10) . . ? C21 Re1 N3 173.34(10) . . ? C22 Re1 N3 93.56(10) . . ? C23 Re1 N1 96.29(10) . . ? C21 Re1 N1 92.56(10) . . ? C22 Re1 N1 177.64(10) . . ? N3 Re1 N1 87.43(8) . . ? C23 Re1 N5 173.10(10) . . ? C21 Re1 N5 96.34(10) . . ? C22 Re1 N5 94.68(10) . . ? N3 Re1 N5 77.03(9) . . ? N1 Re1 N5 83.45(8) . . ? C1 N1 N2 105.2(2) . . ? C1 N1 Re1 128.67(19) . . ? N2 N1 Re1 126.02(17) . . ? C3 N2 N1 110.3(2) . . ? C3 N2 C4 124.2(2) . . ? N1 N2 C4 125.4(2) . . ? C11 N3 N4 105.8(2) . . ? C11 N3 Re1 133.74(18) . . ? N4 N3 Re1 120.41(16) . . ? C13 N4 N3 110.6(2) . . ? C13 N4 C14 127.5(2) . . ? N3 N4 C14 121.9(2) . . ? C19 N5 C9 110.0(2) . . ? C19 N5 Re1 102.05(16) . . ? C9 N5 Re1 119.91(17) . . ? C19 N5 H5N 111(3) . . ? C9 N5 H5N 109(3) . . ? Re1 N5 H5N 104(3) . . ? N1 C1 C2 110.1(3) . . ? N1 C1 C24 123.2(3) . . ? C2 C1 C24 126.7(3) . . ? C3 C2 C1 106.3(3) . . ? C3 C2 H2A 126.9 . . ? C1 C2 H2A 126.9 . . ? N2 C3 C2 108.0(3) . . ? N2 C3 H3A 126.0 . . ? C2 C3 H3A 126.0 . . ? C9 C4 C5 119.4(3) . . ? C9 C4 N2 124.8(2) . . ? C5 C4 N2 115.6(2) . . ? C6 C5 C4 122.0(3) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C5 C6 C7 118.2(3) . . ? C5 C6 C10 121.1(3) . . ? C7 C6 C10 120.8(3) . . ? C8 C7 C6 120.8(3) . . ? C8 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? C7 C8 C9 121.2(3) . . ? C7 C8 H8A 119.4 . . ? C9 C8 H8A 119.4 . . ? C4 C9 C8 118.3(3) . . ? C4 C9 N5 123.8(2) . . ? C8 C9 N5 117.8(2) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 109.9(2) . . ? N3 C11 C25 122.2(2) . . ? C12 C11 C25 127.9(3) . . ? C13 C12 C11 106.1(3) . . ? C13 C12 H12A 127.0 . . ? C11 C12 H12A 127.0 . . ? N4 C13 C12 107.6(3) . . ? N4 C13 H13A 126.2 . . ? C12 C13 H13A 126.2 . . ? C15 C14 C19 120.2(3) . . ? C15 C14 N4 119.7(2) . . ? C19 C14 N4 120.1(2) . . ? C14 C15 C16 120.9(3) . . ? C14 C15 H15A 119.6 . . ? C16 C15 H15A 119.6 . . ? C17 C16 C15 118.5(3) . . ? C17 C16 C20 121.9(3) . . ? C15 C16 C20 119.7(3) . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C19 C18 C17 120.2(3) . . ? C19 C18 H18A 119.9 . . ? C17 C18 H18A 119.9 . . ? C18 C19 C14 119.3(3) . . ? C18 C19 N5 121.9(3) . . ? C14 C19 N5 118.7(2) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 Re1 176.7(3) . . ? O2 C22 Re1 177.5(2) . . ? O3 C23 Re1 177.2(2) . . ? C1 C24 H24A 109.5 . . ? C1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C11 C25 H25A 109.5 . . ? C11 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C11 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? F3 P1 F3 179.998(1) 2_676 . ? F3 P1 F2 89.44(12) 2_676 2_676 ? F3 P1 F2 90.56(12) . 2_676 ? F3 P1 F2 90.56(12) 2_676 . ? F3 P1 F2 89.44(12) . . ? F2 P1 F2 179.999(1) 2_676 . ? F3 P1 F1 89.42(11) 2_676 . ? F3 P1 F1 90.59(11) . . ? F2 P1 F1 89.95(9) 2_676 . ? F2 P1 F1 90.05(9) . . ? F3 P1 F1 90.58(11) 2_676 2_676 ? F3 P1 F1 89.41(11) . 2_676 ? F2 P1 F1 90.05(9) 2_676 2_676 ? F2 P1 F1 89.95(9) . 2_676 ? F1 P1 F1 179.999(1) . 2_676 ? F6 P2 F6 180.0(2) . 2_765 ? F6 P2 F5 89.70(19) . 2_765 ? F6 P2 F5 90.30(19) 2_765 2_765 ? F6 P2 F5 90.30(19) . . ? F6 P2 F5 89.70(19) 2_765 . ? F5 P2 F5 180.00(18) 2_765 . ? F6 P2 F4 89.68(13) . 2_765 ? F6 P2 F4 90.31(13) 2_765 2_765 ? F5 P2 F4 90.78(12) 2_765 2_765 ? F5 P2 F4 89.22(12) . 2_765 ? F6 P2 F4 90.32(13) . . ? F6 P2 F4 89.68(13) 2_765 . ? F5 P2 F4 89.22(12) 2_765 . ? F5 P2 F4 90.78(12) . . ? F4 P2 F4 180.0 2_765 . ? 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 C23 Re1 N1 C1 36.5(2) . . . . ? C21 Re1 N1 C1 -54.3(2) . . . . ? C22 Re1 N1 C1 -113(2) . . . . ? N3 Re1 N1 C1 132.3(2) . . . . ? N5 Re1 N1 C1 -150.4(2) . . . . ? C23 Re1 N1 N2 -146.8(2) . . . . ? C21 Re1 N1 N2 122.4(2) . . . . ? C22 Re1 N1 N2 64(2) . . . . ? N3 Re1 N1 N2 -51.0(2) . . . . ? N5 Re1 N1 N2 26.3(2) . . . . ? C1 N1 N2 C3 0.7(3) . . . . ? Re1 N1 N2 C3 -176.68(18) . . . . ? C1 N1 N2 C4 177.7(2) . . . . ? Re1 N1 N2 C4 0.4(4) . . . . ? C23 Re1 N3 C11 44.9(3) . . . . ? C21 Re1 N3 C11 -141.3(8) . . . . ? C22 Re1 N3 C11 131.0(3) . . . . ? N1 Re1 N3 C11 -51.2(3) . . . . ? N5 Re1 N3 C11 -135.0(3) . . . . ? C23 Re1 N3 N4 -138.1(2) . . . . ? C21 Re1 N3 N4 35.7(9) . . . . ? C22 Re1 N3 N4 -52.0(2) . . . . ? N1 Re1 N3 N4 125.8(2) . . . . ? N5 Re1 N3 N4 41.95(19) . . . . ? C11 N3 N4 C13 0.0(3) . . . . ? Re1 N3 N4 C13 -177.74(19) . . . . ? C11 N3 N4 C14 -177.1(2) . . . . ? Re1 N3 N4 C14 5.1(3) . . . . ? C23 Re1 N5 C19 -71.8(9) . . . . ? C21 Re1 N5 C19 108.06(18) . . . . ? C22 Re1 N5 C19 21.37(18) . . . . ? N3 Re1 N5 C19 -71.21(17) . . . . ? N1 Re1 N5 C19 -160.08(17) . . . . ? C23 Re1 N5 C9 50.0(9) . . . . ? C21 Re1 N5 C9 -130.2(2) . . . . ? C22 Re1 N5 C9 143.1(2) . . . . ? N3 Re1 N5 C9 50.56(19) . . . . ? N1 Re1 N5 C9 -38.30(19) . . . . ? N2 N1 C1 C2 -0.5(3) . . . . ? Re1 N1 C1 C2 176.70(19) . . . . ? N2 N1 C1 C24 179.4(3) . . . . ? Re1 N1 C1 C24 -3.3(4) . . . . ? N1 C1 C2 C3 0.2(3) . . . . ? C24 C1 C2 C3 -179.7(3) . . . . ? N1 N2 C3 C2 -0.5(3) . . . . ? C4 N2 C3 C2 -177.6(3) . . . . ? C1 C2 C3 N2 0.2(3) . . . . ? C3 N2 C4 C9 146.9(3) . . . . ? N1 N2 C4 C9 -29.7(4) . . . . ? C3 N2 C4 C5 -27.9(4) . . . . ? N1 N2 C4 C5 155.4(3) . . . . ? C9 C4 C5 C6 -3.1(4) . . . . ? N2 C4 C5 C6 172.0(3) . . . . ? C4 C5 C6 C7 0.3(4) . . . . ? C4 C5 C6 C10 -178.5(3) . . . . ? C5 C6 C7 C8 1.6(5) . . . . ? C10 C6 C7 C8 -179.5(3) . . . . ? C6 C7 C8 C9 -0.7(5) . . . . ? C5 C4 C9 C8 3.9(4) . . . . ? N2 C4 C9 C8 -170.7(3) . . . . ? C5 C4 C9 N5 -172.7(2) . . . . ? N2 C4 C9 N5 12.7(4) . . . . ? C7 C8 C9 C4 -2.1(4) . . . . ? C7 C8 C9 N5 174.8(3) . . . . ? C19 N5 C9 C4 145.6(3) . . . . ? Re1 N5 C9 C4 27.9(3) . . . . ? C19 N5 C9 C8 -31.0(3) . . . . ? Re1 N5 C9 C8 -148.8(2) . . . . ? N4 N3 C11 C12 0.2(3) . . . . ? Re1 N3 C11 C12 177.5(2) . . . . ? N4 N3 C11 C25 179.2(3) . . . . ? Re1 N3 C11 C25 -3.5(4) . . . . ? N3 C11 C12 C13 -0.3(4) . . . . ? C25 C11 C12 C13 -179.3(3) . . . . ? N3 N4 C13 C12 -0.2(3) . . . . ? C14 N4 C13 C12 176.8(3) . . . . ? C11 C12 C13 N4 0.3(4) . . . . ? C13 N4 C14 C15 -36.7(4) . . . . ? N3 N4 C14 C15 139.9(3) . . . . ? C13 N4 C14 C19 142.1(3) . . . . ? N3 N4 C14 C19 -41.3(4) . . . . ? C19 C14 C15 C16 0.4(4) . . . . ? N4 C14 C15 C16 179.2(3) . . . . ? C14 C15 C16 C17 2.7(4) . . . . ? C14 C15 C16 C20 -177.4(3) . . . . ? C15 C16 C17 C18 -3.1(4) . . . . ? C20 C16 C17 C18 177.1(3) . . . . ? C16 C17 C18 C19 0.3(4) . . . . ? C17 C18 C19 C14 2.8(4) . . . . ? C17 C18 C19 N5 -176.7(2) . . . . ? C15 C14 C19 C18 -3.2(4) . . . . ? N4 C14 C19 C18 178.0(2) . . . . ? C15 C14 C19 N5 176.4(2) . . . . ? N4 C14 C19 N5 -2.4(4) . . . . ? C9 N5 C19 C18 116.7(3) . . . . ? Re1 N5 C19 C18 -115.0(2) . . . . ? C9 N5 C19 C14 -62.9(3) . . . . ? Re1 N5 C19 C14 65.5(3) . . . . ? C23 Re1 C21 O1 97(4) . . . . ? C22 Re1 C21 O1 11(4) . . . . ? N3 Re1 C21 O1 -77(5) . . . . ? N1 Re1 C21 O1 -167(4) . . . . ? N5 Re1 C21 O1 -83(4) . . . . ? C23 Re1 C22 O2 -71(6) . . . . ? C21 Re1 C22 O2 19(6) . . . . ? N3 Re1 C22 O2 -167(6) . . . . ? N1 Re1 C22 O2 78(7) . . . . ? N5 Re1 C22 O2 115(6) . . . . ? C21 Re1 C23 O3 -141(5) . . . . ? C22 Re1 C23 O3 -55(5) . . . . ? N3 Re1 C23 O3 38(5) . . . . ? N1 Re1 C23 O3 126(5) . . . . ? N5 Re1 C23 O3 39(6) . . . . ? 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 N5 H5N F1 0.86(4) 2.10(4) 2.951(3) 173(4) 2_666 _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 67.70 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.714 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.080 #===END data_gard8va_2iPr _database_code_depnum_ccdc_archive 'CCDC 806482' #TrackingRef 'Re_Pincer_full.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H31 F6 N5 O3 P Re' _chemical_formula_weight 828.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.49510(10) _cell_length_b 14.9707(2) _cell_length_c 22.1068(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.1190(10) _cell_angle_gamma 90.00 _cell_volume 3093.56(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7055 _cell_measurement_theta_min 5 _cell_measurement_theta_max 67 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.779 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 8.854 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.2353 _exptl_absorpt_correction_T_max 0.6187 _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25065 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 67.61 _reflns_number_total 5429 _reflns_number_gt 4980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+3.1851P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5429 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0252 _refine_ls_R_factor_gt 0.0219 _refine_ls_wR_factor_ref 0.0554 _refine_ls_wR_factor_gt 0.0541 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 Re1 Re 0.453194(12) 0.716271(8) 0.080292(5) 0.01419(5) Uani 1 1 d . . . O1 O 0.6837(2) 0.56957(14) 0.09540(10) 0.0274(5) Uani 1 1 d . . . O2 O 0.6365(2) 0.82044(14) 0.00331(9) 0.0234(4) Uani 1 1 d . . . O3 O 0.3183(2) 0.63728(15) -0.04435(9) 0.0280(5) Uani 1 1 d . . . N1 N 0.2976(2) 0.82454(15) 0.07754(10) 0.0154(5) Uani 1 1 d . . . N2 N 0.3459(2) 0.91042(15) 0.09122(10) 0.0174(5) Uani 1 1 d . . . N3 N 0.3355(2) 0.63607(15) 0.13865(10) 0.0158(5) Uani 1 1 d . . . N4 N 0.3060(3) 0.66426(16) 0.19463(10) 0.0182(5) Uani 1 1 d . . . N5 N 0.5294(3) 0.79238(16) 0.16853(11) 0.0162(5) Uani 1 1 d . . . H5N H 0.597(4) 0.759(2) 0.1891(15) 0.021(8) Uiso 1 1 d . . . C1 C 0.1550(3) 0.8299(2) 0.06392(12) 0.0187(6) Uani 1 1 d . . . C2 C 0.1119(3) 0.9187(2) 0.06857(14) 0.0234(6) Uani 1 1 d . . . H2A H 0.0166 0.9406 0.0608 0.028 Uiso 1 1 calc R . . C3 C 0.2335(3) 0.9677(2) 0.08640(13) 0.0226(6) Uani 1 1 d . . . H3A H 0.2385 1.0302 0.0940 0.027 Uiso 1 1 calc R . . C4 C 0.4938(3) 0.93201(19) 0.10906(12) 0.0184(6) Uani 1 1 d . . . C5 C 0.5444(3) 1.0114(2) 0.08947(13) 0.0205(6) Uani 1 1 d . . . H5A H 0.4808 1.0504 0.0640 0.025 Uiso 1 1 calc R . . C6 C 0.6885(3) 1.0350(2) 0.10681(13) 0.0240(7) Uani 1 1 d . . . C7 C 0.7796(3) 0.9756(2) 0.14260(13) 0.0215(6) Uani 1 1 d . . . H7A H 0.8784 0.9896 0.1534 0.026 Uiso 1 1 calc R . . C8 C 0.7293(3) 0.8961(2) 0.16294(12) 0.0185(6) Uani 1 1 d . . . H8A H 0.7933 0.8568 0.1879 0.022 Uiso 1 1 calc R . . C9 C 0.5861(3) 0.87387(19) 0.14696(12) 0.0175(6) Uani 1 1 d . . . C10 C 0.7403(4) 1.1231(2) 0.08660(15) 0.0357(8) Uani 1 1 d . . . H10A H 0.8446 1.1263 0.0983 0.054 Uiso 1 1 calc R . . H10B H 0.6965 1.1718 0.1064 0.054 Uiso 1 1 calc R . . H10C H 0.7135 1.1286 0.0419 0.054 Uiso 1 1 calc R . . C11 C 0.3050(3) 0.54796(19) 0.13567(13) 0.0185(6) Uani 1 1 d . . . C12 C 0.2570(3) 0.5210(2) 0.18900(13) 0.0213(6) Uani 1 1 d . . . H12A H 0.2280 0.4626 0.1983 0.026 Uiso 1 1 calc R . . C13 C 0.2600(3) 0.5949(2) 0.22494(14) 0.0228(6) Uani 1 1 d . . . H13A H 0.2342 0.5973 0.2645 0.027 Uiso 1 1 calc R . . C14 C 0.3147(3) 0.7543(2) 0.21667(12) 0.0176(6) Uani 1 1 d . . . C15 C 0.2104(3) 0.7805(2) 0.25005(13) 0.0211(6) Uani 1 1 d . . . H15A H 0.1347 0.7405 0.2538 0.025 Uiso 1 1 calc R . . C16 C 0.2147(3) 0.8642(2) 0.27819(13) 0.0214(6) Uani 1 1 d . . . C17 C 0.3285(3) 0.9200(2) 0.27279(13) 0.0209(6) Uani 1 1 d . . . H17A H 0.3366 0.9763 0.2930 0.025 Uiso 1 1 calc R . . C18 C 0.4297(3) 0.8951(2) 0.23859(13) 0.0203(6) Uani 1 1 d . . . H18A H 0.5055 0.9352 0.2352 0.024 Uiso 1 1 calc R . . C19 C 0.4245(3) 0.81331(19) 0.20898(12) 0.0163(6) Uani 1 1 d . . . C20 C 0.0980(3) 0.8949(2) 0.31160(15) 0.0287(7) Uani 1 1 d . . . H20A H 0.0179 0.8527 0.3039 0.043 Uiso 0.50 1 calc PR . . H20B H 0.0650 0.9543 0.2969 0.043 Uiso 0.50 1 calc PR . . H20C H 0.1353 0.8975 0.3558 0.043 Uiso 0.50 1 calc PR . . H20D H 0.1276 0.9503 0.3338 0.043 Uiso 0.50 1 calc PR . . H20E H 0.0805 0.8487 0.3408 0.043 Uiso 0.50 1 calc PR . . H20F H 0.0102 0.9055 0.2819 0.043 Uiso 0.50 1 calc PR . . C21 C 0.5987(3) 0.62417(19) 0.09033(13) 0.0183(6) Uani 1 1 d . . . C22 C 0.5681(3) 0.78331(18) 0.03273(13) 0.0180(6) Uani 1 1 d . . . C23 C 0.3681(3) 0.66504(19) 0.00279(13) 0.0193(6) Uani 1 1 d . . . C24 C 0.0637(3) 0.7490(2) 0.04665(13) 0.0195(6) Uani 1 1 d . . . H24A H 0.1281 0.6960 0.0476 0.023 Uiso 1 1 calc R . . C25 C -0.0220(4) 0.7580(2) -0.01865(14) 0.0294(7) Uani 1 1 d . . . H25A H 0.0440 0.7625 -0.0480 0.044 Uiso 1 1 calc R . . H25B H -0.0815 0.8118 -0.0213 0.044 Uiso 1 1 calc R . . H25C H -0.0833 0.7054 -0.0284 0.044 Uiso 1 1 calc R . . C26 C -0.0354(3) 0.7333(2) 0.09323(15) 0.0295(7) Uani 1 1 d . . . H26A H 0.0217 0.7286 0.1346 0.044 Uiso 1 1 calc R . . H26B H -0.0891 0.6778 0.0831 0.044 Uiso 1 1 calc R . . H26C H -0.1023 0.7834 0.0918 0.044 Uiso 1 1 calc R . . C27 C 0.3117(3) 0.49082(19) 0.08031(13) 0.0194(6) Uani 1 1 d . . . H27A H 0.3808 0.5185 0.0565 0.023 Uiso 1 1 calc R . . C28 C 0.3614(3) 0.3958(2) 0.09797(15) 0.0268(7) Uani 1 1 d . . . H28A H 0.4601 0.3972 0.1204 0.040 Uiso 1 1 calc R . . H28B H 0.3571 0.3597 0.0607 0.040 Uiso 1 1 calc R . . H28C H 0.2991 0.3694 0.1241 0.040 Uiso 1 1 calc R . . C29 C 0.1636(3) 0.4890(2) 0.03949(14) 0.0266(7) Uani 1 1 d . . . H29A H 0.1328 0.5502 0.0283 0.040 Uiso 1 1 calc R . . H29B H 0.0949 0.4609 0.0619 0.040 Uiso 1 1 calc R . . H29C H 0.1682 0.4547 0.0021 0.040 Uiso 1 1 calc R . . P1 P 0.80237(8) 0.67045(5) 0.29025(3) 0.02351(17) Uani 1 1 d . . . F1 F 0.7521(2) 0.77351(12) 0.28451(9) 0.0326(4) Uani 1 1 d . . . F6 F 0.9532(2) 0.69989(14) 0.32893(11) 0.0472(6) Uani 1 1 d . . . F5 F 0.8521(2) 0.56853(12) 0.29535(9) 0.0365(5) Uani 1 1 d . . . F4 F 0.7391(3) 0.66188(15) 0.35144(10) 0.0495(6) Uani 1 1 d . . . F3 F 0.8667(3) 0.68217(16) 0.22837(10) 0.0515(6) Uani 1 1 d . . . F2 F 0.6527(2) 0.64287(14) 0.24937(11) 0.0475(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.01432(8) 0.01384(8) 0.01449(8) 0.00019(5) 0.00276(5) -0.00081(4) O1 0.0235(12) 0.0215(12) 0.0380(13) 0.0018(10) 0.0072(9) 0.0070(9) O2 0.0236(11) 0.0240(11) 0.0245(11) 0.0036(9) 0.0091(9) -0.0013(9) O3 0.0321(12) 0.0315(13) 0.0199(11) -0.0049(9) 0.0034(9) -0.0055(10) N1 0.0174(12) 0.0134(12) 0.0154(11) -0.0011(9) 0.0025(9) -0.0016(9) N2 0.0184(12) 0.0160(12) 0.0171(11) -0.0001(9) 0.0010(9) -0.0021(9) N3 0.0165(12) 0.0149(12) 0.0160(11) 0.0021(9) 0.0027(9) -0.0023(9) N4 0.0210(13) 0.0181(13) 0.0163(11) -0.0014(9) 0.0052(9) -0.0033(9) N5 0.0143(12) 0.0186(13) 0.0151(11) -0.0003(9) 0.0012(10) 0.0002(9) C1 0.0175(15) 0.0226(16) 0.0154(13) -0.0008(11) 0.0014(11) 0.0015(11) C2 0.0183(15) 0.0254(16) 0.0256(15) -0.0039(13) 0.0016(12) 0.0056(12) C3 0.0266(16) 0.0165(15) 0.0238(15) -0.0027(12) 0.0020(12) 0.0050(12) C4 0.0201(15) 0.0199(15) 0.0142(13) -0.0029(11) 0.0003(11) -0.0001(11) C5 0.0250(16) 0.0189(15) 0.0162(13) 0.0006(11) -0.0003(12) -0.0032(12) C6 0.0322(18) 0.0241(16) 0.0157(14) -0.0025(12) 0.0040(12) -0.0098(13) C7 0.0181(15) 0.0296(17) 0.0172(14) -0.0052(12) 0.0043(11) -0.0080(12) C8 0.0198(15) 0.0215(15) 0.0143(13) -0.0024(11) 0.0038(11) -0.0005(11) C9 0.0227(15) 0.0173(15) 0.0127(13) -0.0007(11) 0.0032(11) -0.0014(11) C10 0.045(2) 0.0321(19) 0.0282(17) 0.0051(14) 0.0002(15) -0.0189(16) C11 0.0134(14) 0.0193(15) 0.0216(14) 0.0012(12) -0.0003(11) -0.0016(11) C12 0.0224(16) 0.0180(15) 0.0236(15) 0.0044(12) 0.0045(12) -0.0042(11) C13 0.0268(16) 0.0206(16) 0.0221(15) 0.0024(12) 0.0078(12) -0.0037(12) C14 0.0198(15) 0.0180(14) 0.0143(13) 0.0004(11) 0.0016(11) -0.0003(11) C15 0.0182(15) 0.0259(17) 0.0189(14) 0.0021(12) 0.0021(12) -0.0032(12) C16 0.0182(15) 0.0268(17) 0.0185(14) -0.0001(12) 0.0008(11) 0.0013(12) C17 0.0244(16) 0.0189(15) 0.0187(14) -0.0019(11) 0.0019(12) -0.0006(12) C18 0.0202(15) 0.0217(16) 0.0181(14) -0.0001(12) 0.0011(11) -0.0023(12) C19 0.0155(14) 0.0194(14) 0.0131(13) 0.0013(11) -0.0003(11) -0.0011(11) C20 0.0242(17) 0.0350(19) 0.0281(16) -0.0064(14) 0.0079(13) 0.0000(13) C21 0.0181(15) 0.0181(15) 0.0200(14) -0.0009(11) 0.0069(11) -0.0052(12) C22 0.0164(14) 0.0166(14) 0.0200(14) -0.0008(11) 0.0010(12) 0.0021(11) C23 0.0195(15) 0.0177(15) 0.0214(15) 0.0002(12) 0.0056(12) -0.0009(11) C24 0.0161(14) 0.0196(15) 0.0226(15) -0.0012(12) 0.0024(12) -0.0005(11) C25 0.0280(18) 0.0361(19) 0.0233(16) -0.0016(14) 0.0021(13) -0.0122(14) C26 0.0229(17) 0.041(2) 0.0251(16) 0.0006(14) 0.0038(13) -0.0077(14) C27 0.0211(15) 0.0159(15) 0.0212(14) -0.0010(11) 0.0041(12) -0.0036(11) C28 0.0292(17) 0.0208(16) 0.0294(16) -0.0025(13) 0.0022(13) 0.0003(13) C29 0.0253(17) 0.0261(17) 0.0267(16) -0.0049(13) -0.0005(13) -0.0003(13) P1 0.0259(4) 0.0218(4) 0.0212(4) 0.0038(3) -0.0004(3) 0.0007(3) F1 0.0437(12) 0.0219(10) 0.0298(10) 0.0041(8) -0.0007(9) 0.0029(8) F6 0.0391(13) 0.0377(13) 0.0566(14) 0.0055(10) -0.0144(11) -0.0042(9) F5 0.0387(11) 0.0249(10) 0.0425(11) 0.0005(8) -0.0021(9) 0.0094(8) F4 0.0734(16) 0.0393(13) 0.0434(12) 0.0148(10) 0.0314(11) 0.0110(11) F3 0.0705(16) 0.0532(14) 0.0364(12) 0.0078(10) 0.0253(11) 0.0066(12) F2 0.0350(12) 0.0281(11) 0.0692(15) 0.0028(10) -0.0193(10) -0.0020(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C23 1.921(3) . ? Re1 C22 1.925(3) . ? Re1 C21 1.937(3) . ? Re1 N1 2.187(2) . ? Re1 N3 2.205(2) . ? Re1 N5 2.265(2) . ? O1 C21 1.140(4) . ? O2 C22 1.141(4) . ? O3 C23 1.144(4) . ? N1 C1 1.336(4) . ? N1 N2 1.381(3) . ? N2 C3 1.359(4) . ? N2 C4 1.427(4) . ? N3 C11 1.349(4) . ? N3 N4 1.382(3) . ? N4 C13 1.349(4) . ? N4 C14 1.431(4) . ? N5 C9 1.448(4) . ? N5 C19 1.484(4) . ? N5 H5N 0.87(4) . ? C1 C2 1.400(4) . ? C1 C24 1.499(4) . ? C2 C3 1.367(4) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C5 1.380(4) . ? C4 C9 1.404(4) . ? C5 C6 1.400(4) . ? C5 H5A 0.9500 . ? C6 C7 1.387(4) . ? C6 C10 1.502(4) . ? C7 C8 1.386(4) . ? C7 H7A 0.9500 . ? C8 C9 1.384(4) . ? C8 H8A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.397(4) . ? C11 C27 1.504(4) . ? C12 C13 1.360(4) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.391(4) . ? C14 C19 1.399(4) . ? C15 C16 1.397(4) . ? C15 H15A 0.9500 . ? C16 C17 1.388(4) . ? C16 C20 1.507(4) . ? C17 C18 1.374(4) . ? C17 H17A 0.9500 . ? C18 C19 1.386(4) . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C20 H20D 0.9800 . ? C20 H20E 0.9800 . ? C20 H20F 0.9800 . ? C24 C26 1.530(4) . ? C24 C25 1.533(4) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.529(4) . ? C27 C29 1.532(4) . ? C27 H27A 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? P1 F4 1.579(2) . ? P1 F6 1.596(2) . ? P1 F5 1.595(2) . ? P1 F2 1.599(2) . ? P1 F3 1.603(2) . ? P1 F1 1.6135(19) . ? 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 C23 Re1 C22 84.90(12) . . ? C23 Re1 C21 89.88(12) . . ? C22 Re1 C21 88.41(11) . . ? C23 Re1 N1 95.44(10) . . ? C22 Re1 N1 92.49(10) . . ? C21 Re1 N1 174.67(10) . . ? C23 Re1 N3 97.31(10) . . ? C22 Re1 N3 176.01(10) . . ? C21 Re1 N3 88.28(10) . . ? N1 Re1 N3 90.61(8) . . ? C23 Re1 N5 171.71(11) . . ? C22 Re1 N5 94.72(10) . . ? C21 Re1 N5 98.40(10) . . ? N1 Re1 N5 76.30(9) . . ? N3 Re1 N5 83.57(8) . . ? C1 N1 N2 106.2(2) . . ? C1 N1 Re1 134.67(19) . . ? N2 N1 Re1 119.16(17) . . ? C3 N2 N1 110.1(2) . . ? C3 N2 C4 126.9(2) . . ? N1 N2 C4 123.0(2) . . ? C11 N3 N4 105.5(2) . . ? C11 N3 Re1 129.05(19) . . ? N4 N3 Re1 124.13(17) . . ? C13 N4 N3 110.1(2) . . ? C13 N4 C14 124.1(2) . . ? N3 N4 C14 125.7(2) . . ? C9 N5 C19 110.4(2) . . ? C9 N5 Re1 102.78(16) . . ? C19 N5 Re1 118.60(17) . . ? C9 N5 H5N 111(2) . . ? C19 N5 H5N 109(2) . . ? Re1 N5 H5N 105(2) . . ? N1 C1 C2 109.7(3) . . ? N1 C1 C24 121.8(3) . . ? C2 C1 C24 128.4(3) . . ? C3 C2 C1 106.7(3) . . ? C3 C2 H2A 126.6 . . ? C1 C2 H2A 126.6 . . ? N2 C3 C2 107.2(3) . . ? N2 C3 H3A 126.4 . . ? C2 C3 H3A 126.4 . . ? C5 C4 C9 120.4(3) . . ? C5 C4 N2 119.2(3) . . ? C9 C4 N2 120.4(3) . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C7 C6 C5 118.4(3) . . ? C7 C6 C10 121.9(3) . . ? C5 C6 C10 119.7(3) . . ? C6 C7 C8 121.3(3) . . ? C6 C7 H7A 119.4 . . ? C8 C7 H7A 119.4 . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? C8 C9 C4 119.1(3) . . ? C8 C9 N5 121.6(3) . . ? C4 C9 N5 119.3(3) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 109.9(3) . . ? N3 C11 C27 123.8(3) . . ? C12 C11 C27 126.1(3) . . ? C13 C12 C11 106.3(3) . . ? C13 C12 H12A 126.8 . . ? C11 C12 H12A 126.8 . . ? N4 C13 C12 108.2(3) . . ? N4 C13 H13A 125.9 . . ? C12 C13 H13A 125.9 . . ? C15 C14 C19 120.1(3) . . ? C15 C14 N4 116.2(3) . . ? C19 C14 N4 123.6(3) . . ? C14 C15 C16 121.4(3) . . ? C14 C15 H15A 119.3 . . ? C16 C15 H15A 119.3 . . ? C17 C16 C15 117.6(3) . . ? C17 C16 C20 120.6(3) . . ? C15 C16 C20 121.7(3) . . ? C18 C17 C16 121.0(3) . . ? C18 C17 H17A 119.5 . . ? C16 C17 H17A 119.5 . . ? C17 C18 C19 121.9(3) . . ? C17 C18 H18A 119.0 . . ? C19 C18 H18A 119.0 . . ? C18 C19 C14 117.8(3) . . ? C18 C19 N5 120.0(2) . . ? C14 C19 N5 122.2(2) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C20 H20D 109.5 . . ? H20A C20 H20D 141.1 . . ? H20B C20 H20D 56.3 . . ? H20C C20 H20D 56.3 . . ? C16 C20 H20E 109.5 . . ? H20A C20 H20E 56.3 . . ? H20B C20 H20E 141.1 . . ? H20C C20 H20E 56.3 . . ? H20D C20 H20E 109.5 . . ? C16 C20 H20F 109.5 . . ? H20A C20 H20F 56.3 . . ? H20B C20 H20F 56.3 . . ? H20C C20 H20F 141.1 . . ? H20D C20 H20F 109.5 . . ? H20E C20 H20F 109.5 . . ? O1 C21 Re1 179.0(3) . . ? O2 C22 Re1 177.6(2) . . ? O3 C23 Re1 177.6(3) . . ? C1 C24 C26 110.5(2) . . ? C1 C24 C25 110.9(2) . . ? C26 C24 C25 111.1(2) . . ? C1 C24 H24A 108.1 . . ? C26 C24 H24A 108.1 . . ? C25 C24 H24A 108.1 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C11 C27 C28 112.2(2) . . ? C11 C27 C29 108.9(2) . . ? C28 C27 C29 110.1(2) . . ? C11 C27 H27A 108.5 . . ? C28 C27 H27A 108.5 . . ? C29 C27 H27A 108.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? F4 P1 F6 90.25(14) . . ? F4 P1 F5 90.82(11) . . ? F6 P1 F5 89.97(11) . . ? F4 P1 F2 91.65(14) . . ? F6 P1 F2 177.89(14) . . ? F5 P1 F2 90.91(11) . . ? F4 P1 F3 178.37(13) . . ? F6 P1 F3 89.22(14) . . ? F5 P1 F3 90.72(12) . . ? F2 P1 F3 88.85(14) . . ? F4 P1 F1 89.60(11) . . ? F6 P1 F1 90.20(11) . . ? F5 P1 F1 179.55(11) . . ? F2 P1 F1 88.91(11) . . ? F3 P1 F1 88.86(12) . . ? 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 C23 Re1 N1 C1 45.7(3) . . . . ? C22 Re1 N1 C1 130.8(3) . . . . ? C21 Re1 N1 C1 -129.6(10) . . . . ? N3 Re1 N1 C1 -51.7(3) . . . . ? N5 Re1 N1 C1 -134.9(3) . . . . ? C23 Re1 N1 N2 -132.98(19) . . . . ? C22 Re1 N1 N2 -47.9(2) . . . . ? C21 Re1 N1 N2 51.7(11) . . . . ? N3 Re1 N1 N2 129.62(19) . . . . ? N5 Re1 N1 N2 46.38(18) . . . . ? C1 N1 N2 C3 0.4(3) . . . . ? Re1 N1 N2 C3 179.42(18) . . . . ? C1 N1 N2 C4 179.0(2) . . . . ? Re1 N1 N2 C4 -1.9(3) . . . . ? C23 Re1 N3 C11 42.6(3) . . . . ? C22 Re1 N3 C11 -81.0(15) . . . . ? C21 Re1 N3 C11 -47.1(2) . . . . ? N1 Re1 N3 C11 138.2(2) . . . . ? N5 Re1 N3 C11 -145.7(2) . . . . ? C23 Re1 N3 N4 -152.7(2) . . . . ? C22 Re1 N3 N4 83.8(15) . . . . ? C21 Re1 N3 N4 117.7(2) . . . . ? N1 Re1 N3 N4 -57.1(2) . . . . ? N5 Re1 N3 N4 19.0(2) . . . . ? C11 N3 N4 C13 0.5(3) . . . . ? Re1 N3 N4 C13 -167.27(19) . . . . ? C11 N3 N4 C14 -176.4(3) . . . . ? Re1 N3 N4 C14 15.9(3) . . . . ? C23 Re1 N5 C9 -67.6(7) . . . . ? C22 Re1 N5 C9 19.42(19) . . . . ? C21 Re1 N5 C9 108.51(18) . . . . ? N1 Re1 N5 C9 -72.00(17) . . . . ? N3 Re1 N5 C9 -164.20(18) . . . . ? C23 Re1 N5 C19 54.5(8) . . . . ? C22 Re1 N5 C19 141.5(2) . . . . ? C21 Re1 N5 C19 -129.5(2) . . . . ? N1 Re1 N5 C19 50.04(19) . . . . ? N3 Re1 N5 C19 -42.16(19) . . . . ? N2 N1 C1 C2 0.2(3) . . . . ? Re1 N1 C1 C2 -178.6(2) . . . . ? N2 N1 C1 C24 -179.8(2) . . . . ? Re1 N1 C1 C24 1.4(4) . . . . ? N1 C1 C2 C3 -0.8(3) . . . . ? C24 C1 C2 C3 179.3(3) . . . . ? N1 N2 C3 C2 -0.9(3) . . . . ? C4 N2 C3 C2 -179.5(3) . . . . ? C1 C2 C3 N2 1.0(3) . . . . ? C3 N2 C4 C5 -38.1(4) . . . . ? N1 N2 C4 C5 143.5(3) . . . . ? C3 N2 C4 C9 140.8(3) . . . . ? N1 N2 C4 C9 -37.6(4) . . . . ? C9 C4 C5 C6 0.3(4) . . . . ? N2 C4 C5 C6 179.2(3) . . . . ? C4 C5 C6 C7 1.8(4) . . . . ? C4 C5 C6 C10 -178.1(3) . . . . ? C5 C6 C7 C8 -2.4(4) . . . . ? C10 C6 C7 C8 177.4(3) . . . . ? C6 C7 C8 C9 1.0(4) . . . . ? C7 C8 C9 C4 1.2(4) . . . . ? C7 C8 C9 N5 -178.6(2) . . . . ? C5 C4 C9 C8 -1.8(4) . . . . ? N2 C4 C9 C8 179.3(2) . . . . ? C5 C4 C9 N5 178.0(2) . . . . ? N2 C4 C9 N5 -0.9(4) . . . . ? C19 N5 C9 C8 115.7(3) . . . . ? Re1 N5 C9 C8 -116.9(2) . . . . ? C19 N5 C9 C4 -64.1(3) . . . . ? Re1 N5 C9 C4 63.3(3) . . . . ? N4 N3 C11 C12 0.0(3) . . . . ? Re1 N3 C11 C12 166.94(19) . . . . ? N4 N3 C11 C27 175.5(2) . . . . ? Re1 N3 C11 C27 -17.5(4) . . . . ? N3 C11 C12 C13 -0.5(3) . . . . ? C27 C11 C12 C13 -175.9(3) . . . . ? N3 N4 C13 C12 -0.8(3) . . . . ? C14 N4 C13 C12 176.1(3) . . . . ? C11 C12 C13 N4 0.8(3) . . . . ? C13 N4 C14 C15 -33.9(4) . . . . ? N3 N4 C14 C15 142.6(3) . . . . ? C13 N4 C14 C19 142.7(3) . . . . ? N3 N4 C14 C19 -40.8(4) . . . . ? C19 C14 C15 C16 -2.1(4) . . . . ? N4 C14 C15 C16 174.6(3) . . . . ? C14 C15 C16 C17 -1.3(4) . . . . ? C14 C15 C16 C20 176.7(3) . . . . ? C15 C16 C17 C18 2.9(4) . . . . ? C20 C16 C17 C18 -175.2(3) . . . . ? C16 C17 C18 C19 -1.1(4) . . . . ? C17 C18 C19 C14 -2.3(4) . . . . ? C17 C18 C19 N5 175.1(3) . . . . ? C15 C14 C19 C18 3.8(4) . . . . ? N4 C14 C19 C18 -172.7(3) . . . . ? C15 C14 C19 N5 -173.5(3) . . . . ? N4 C14 C19 N5 10.1(4) . . . . ? C9 N5 C19 C18 -23.0(3) . . . . ? Re1 N5 C19 C18 -141.1(2) . . . . ? C9 N5 C19 C14 154.2(3) . . . . ? Re1 N5 C19 C14 36.1(3) . . . . ? C23 Re1 C21 O1 9(16) . . . . ? C22 Re1 C21 O1 -76(16) . . . . ? N1 Re1 C21 O1 -175(100) . . . . ? N3 Re1 C21 O1 107(16) . . . . ? N5 Re1 C21 O1 -170(100) . . . . ? C23 Re1 C22 O2 -38(6) . . . . ? C21 Re1 C22 O2 52(6) . . . . ? N1 Re1 C22 O2 -133(6) . . . . ? N3 Re1 C22 O2 86(7) . . . . ? N5 Re1 C22 O2 150(6) . . . . ? C22 Re1 C23 O3 -30(6) . . . . ? C21 Re1 C23 O3 -119(6) . . . . ? N1 Re1 C23 O3 62(6) . . . . ? N3 Re1 C23 O3 153(6) . . . . ? N5 Re1 C23 O3 57(7) . . . . ? N1 C1 C24 C26 118.0(3) . . . . ? C2 C1 C24 C26 -62.1(4) . . . . ? N1 C1 C24 C25 -118.5(3) . . . . ? C2 C1 C24 C25 61.5(4) . . . . ? N3 C11 C27 C28 145.4(3) . . . . ? C12 C11 C27 C28 -39.8(4) . . . . ? N3 C11 C27 C29 -92.4(3) . . . . ? C12 C11 C27 C29 82.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 67.61 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.682 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.079 #===END data_gard8ma_3Me _database_code_depnum_ccdc_archive 'CCDC 806483' #TrackingRef 'Re_Pincer_full.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H22 N5 O3 Re' _chemical_formula_weight 626.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -5.2083 5.8923 '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' 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 30.8054(4) _cell_length_b 11.4882(2) _cell_length_c 13.4222(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.7730(10) _cell_angle_gamma 90.00 _cell_volume 4733.63(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8940 _cell_measurement_theta_min 3 _cell_measurement_theta_max 67 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2448 _exptl_absorpt_coefficient_mu 10.350 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.1902 _exptl_absorpt_correction_T_max 0.5756 _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19490 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 68.02 _reflns_number_total 4198 _reflns_number_gt 3560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+17.6549P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4198 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.110859(4) 0.251958(10) 0.410196(10) 0.01462(8) Uani 1 1 d . . . O1 O 0.15089(11) 0.2403(2) 0.2080(2) 0.0363(7) Uani 1 1 d . . . O3 O 0.04560(8) 0.4374(2) 0.32758(19) 0.0308(6) Uani 1 1 d . . . O2 O 0.04340(8) 0.0807(2) 0.31535(18) 0.0272(6) Uani 1 1 d . . . N1 N 0.08489(10) 0.25189(19) 0.5573(2) 0.0153(6) Uani 1 1 d . . . N2 N 0.07639(9) 0.1488(2) 0.6037(2) 0.0188(6) Uani 1 1 d . . . N3 N 0.16390(9) 0.3702(3) 0.4660(2) 0.0245(6) Uani 1 1 d . . . N4 N 0.19937(9) 0.3322(2) 0.5267(2) 0.0226(6) Uani 1 1 d . . . N5 N 0.14953(9) 0.1193(2) 0.4925(2) 0.0222(6) Uani 1 1 d . . . C1 C 0.07370(10) 0.3368(3) 0.6185(2) 0.0197(7) Uani 1 1 d . . . C2 C 0.05816(12) 0.2869(4) 0.7048(3) 0.0281(8) Uani 1 1 d . . . H2A H 0.0480 0.3272 0.7601 0.034 Uiso 1 1 calc R . . C3 C 0.06061(11) 0.1691(3) 0.6931(3) 0.0256(8) Uani 1 1 d . . . H3A H 0.0527 0.1118 0.7394 0.031 Uiso 1 1 calc R . . C4 C 0.08321(11) 0.0384(3) 0.5574(3) 0.0211(7) Uani 1 1 d . . . C5 C 0.05324(11) -0.0494(3) 0.5651(3) 0.0239(7) Uani 1 1 d . . . H5A H 0.0284 -0.0364 0.6010 0.029 Uiso 1 1 calc R . . C6 C 0.05918(11) -0.1577(3) 0.5205(3) 0.0254(7) Uani 1 1 d . . . C7 C 0.09513(12) -0.1718(3) 0.4653(3) 0.0274(8) Uani 1 1 d . . . H7A H 0.0994 -0.2442 0.4332 0.033 Uiso 1 1 calc R . . C8 C 0.12487(11) -0.0829(3) 0.4561(3) 0.0256(7) Uani 1 1 d . . . H8A H 0.1491 -0.0953 0.4179 0.031 Uiso 1 1 calc R . . C9 C 0.11994(11) 0.0242(3) 0.5017(3) 0.0223(7) Uani 1 1 d . . . C10 C 0.02707(12) -0.2536(3) 0.5316(3) 0.0263(8) Uani 1 1 d . . . H10A H 0.0321 -0.3162 0.4844 0.039 Uiso 1 1 calc R . . H10B H -0.0026 -0.2234 0.5178 0.039 Uiso 1 1 calc R . . H10C H 0.0306 -0.2841 0.6000 0.039 Uiso 1 1 calc R . . C11 C 0.17887(12) 0.4635(3) 0.4165(3) 0.0269(8) Uani 1 1 d . . . C12 C 0.22241(12) 0.4836(3) 0.4462(3) 0.0272(8) Uani 1 1 d . . . H12A H 0.2403 0.5438 0.4234 0.033 Uiso 1 1 calc R . . C13 C 0.23443(11) 0.3994(3) 0.5148(3) 0.0246(7) Uani 1 1 d . . . H13A H 0.2626 0.3898 0.5482 0.030 Uiso 1 1 calc R . . C14 C 0.19702(11) 0.2456(2) 0.6019(3) 0.0163(7) Uani 1 1 d . . . C15 C 0.22128(11) 0.2635(3) 0.6923(3) 0.0219(7) Uani 1 1 d . . . H15A H 0.2361 0.3356 0.7023 0.026 Uiso 1 1 calc R . . C16 C 0.22521(12) 0.1831(3) 0.7682(3) 0.0275(8) Uani 1 1 d . . . C17 C 0.20310(11) 0.0784(3) 0.7494(3) 0.0263(8) Uani 1 1 d . . . H17A H 0.2055 0.0189 0.7988 0.032 Uiso 1 1 calc R . . C18 C 0.17793(11) 0.0585(3) 0.6616(3) 0.0238(7) Uani 1 1 d . . . H18A H 0.1629 -0.0135 0.6535 0.029 Uiso 1 1 calc R . . C19 C 0.17345(10) 0.1408(3) 0.5826(3) 0.0221(7) Uani 1 1 d . . . C20 C 0.25097(13) 0.2074(4) 0.8662(3) 0.0349(9) Uani 1 1 d . . . H20A H 0.2644 0.2845 0.8638 0.052 Uiso 1 1 calc R . . H20B H 0.2737 0.1482 0.8782 0.052 Uiso 1 1 calc R . . H20C H 0.2315 0.2052 0.9203 0.052 Uiso 1 1 calc R . . C21 C 0.13633(13) 0.2457(3) 0.2844(3) 0.0229(8) Uani 1 1 d . . . C22 C 0.06880(10) 0.1438(3) 0.3531(2) 0.0190(7) Uani 1 1 d . . . C23 C 0.07111(11) 0.3695(3) 0.3572(3) 0.0209(7) Uani 1 1 d . . . C24 C 0.07684(13) 0.4621(3) 0.5931(3) 0.0311(8) Uani 1 1 d . . . H24A H 0.1055 0.4780 0.5693 0.047 Uiso 1 1 calc R . . H24B H 0.0731 0.5092 0.6527 0.047 Uiso 1 1 calc R . . H24C H 0.0540 0.4819 0.5406 0.047 Uiso 1 1 calc R . . C25 C 0.15104(13) 0.5315(3) 0.3416(3) 0.0359(9) Uani 1 1 d . . . H25A H 0.1241 0.5545 0.3704 0.054 Uiso 1 1 calc R . . H25B H 0.1439 0.4835 0.2821 0.054 Uiso 1 1 calc R . . H25C H 0.1668 0.6012 0.3228 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.01590(11) 0.01516(11) 0.01306(11) 0.00089(5) 0.00278(7) -0.00064(5) O1 0.0425(17) 0.0452(18) 0.0240(16) -0.0030(11) 0.0186(14) -0.0057(12) O3 0.0309(14) 0.0315(14) 0.0297(14) 0.0118(12) 0.0007(11) 0.0079(12) O2 0.0261(12) 0.0316(14) 0.0235(13) -0.0078(11) 0.0002(10) -0.0060(11) N1 0.0170(14) 0.0156(15) 0.0136(14) 0.0033(10) 0.0019(11) -0.0004(9) N2 0.0215(13) 0.0170(13) 0.0188(14) 0.0037(11) 0.0057(11) 0.0001(11) N3 0.0270(15) 0.0208(15) 0.0250(16) 0.0025(12) -0.0020(13) -0.0035(12) N4 0.0234(14) 0.0232(15) 0.0214(14) 0.0016(12) 0.0040(12) -0.0028(12) N5 0.0246(14) 0.0171(14) 0.0247(16) 0.0000(12) 0.0003(12) 0.0022(12) C1 0.0181(15) 0.0200(16) 0.0207(17) -0.0051(14) -0.0001(13) 0.0037(13) C2 0.0281(18) 0.039(2) 0.0181(18) -0.0042(16) 0.0054(14) 0.0048(17) C3 0.0268(18) 0.032(2) 0.0189(17) 0.0052(15) 0.0060(14) -0.0017(15) C4 0.0227(16) 0.0166(16) 0.0236(18) 0.0001(14) -0.0017(14) -0.0001(13) C5 0.0218(16) 0.0265(18) 0.0238(18) 0.0016(15) 0.0036(14) 0.0016(14) C6 0.0260(17) 0.0220(17) 0.0277(19) 0.0020(15) -0.0013(15) -0.0001(14) C7 0.0305(18) 0.0238(18) 0.0281(19) -0.0025(15) 0.0031(15) 0.0013(15) C8 0.0266(17) 0.0224(17) 0.0282(19) -0.0028(15) 0.0049(15) 0.0024(14) C9 0.0201(16) 0.0234(17) 0.0234(18) 0.0034(14) 0.0022(14) -0.0013(13) C10 0.0229(18) 0.0189(19) 0.037(2) 0.0001(14) 0.0037(16) -0.0010(12) C11 0.0310(19) 0.0211(17) 0.0295(19) 0.0012(15) 0.0091(15) -0.0009(15) C12 0.0320(19) 0.0193(17) 0.032(2) 0.0004(15) 0.0098(16) -0.0052(14) C13 0.0224(16) 0.0240(17) 0.0278(19) -0.0059(15) 0.0040(14) -0.0012(14) C14 0.0161(15) 0.0167(17) 0.0167(17) 0.0010(12) 0.0050(13) 0.0019(11) C15 0.0195(17) 0.0264(18) 0.0203(18) -0.0046(14) 0.0058(14) -0.0009(13) C16 0.0285(18) 0.0303(19) 0.0242(18) -0.0011(15) 0.0054(15) 0.0049(15) C17 0.0274(18) 0.0289(18) 0.0231(18) 0.0051(15) 0.0047(15) 0.0038(15) C18 0.0224(17) 0.0231(17) 0.0264(18) 0.0050(14) 0.0055(14) -0.0016(14) C19 0.0189(16) 0.0244(17) 0.0234(18) 0.0002(14) 0.0045(14) 0.0042(13) C20 0.038(2) 0.041(2) 0.025(2) 0.0005(18) 0.0013(17) 0.0013(19) C21 0.0247(19) 0.023(2) 0.021(2) 0.0004(13) 0.0043(16) -0.0020(13) C22 0.0182(15) 0.0239(17) 0.0156(16) 0.0010(14) 0.0056(13) 0.0019(14) C23 0.0224(16) 0.0245(18) 0.0164(17) 0.0038(14) 0.0053(14) 0.0002(15) C24 0.044(2) 0.0181(18) 0.031(2) -0.0032(15) 0.0003(17) 0.0017(16) C25 0.036(2) 0.028(2) 0.043(2) 0.0120(17) 0.0013(17) -0.0058(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C22 1.910(3) . ? Re1 C23 1.919(3) . ? Re1 C21 1.921(4) . ? Re1 N5 2.178(3) . ? Re1 N1 2.191(3) . ? Re1 N3 2.207(3) . ? O1 C21 1.155(5) . ? O3 C23 1.154(4) . ? O2 C22 1.152(4) . ? N1 C1 1.339(4) . ? N1 N2 1.373(4) . ? N2 C3 1.352(4) . ? N2 C4 1.435(4) . ? N3 C11 1.363(4) . ? N3 N4 1.378(4) . ? N4 C13 1.348(4) . ? N4 C14 1.423(4) . ? N5 C19 1.385(4) . ? N5 C9 1.435(4) . ? C1 C2 1.412(5) . ? C1 C24 1.484(5) . ? C2 C3 1.365(5) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C5 1.378(5) . ? C4 C9 1.416(5) . ? C5 C6 1.399(5) . ? C5 H5A 0.9500 . ? C6 C7 1.392(5) . ? C6 C10 1.497(5) . ? C7 C8 1.385(5) . ? C7 H7A 0.9500 . ? C8 C9 1.388(5) . ? C8 H8A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.386(5) . ? C11 C25 1.487(5) . ? C12 C13 1.366(5) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.386(5) . ? C14 C19 1.419(4) . ? C15 C16 1.373(5) . ? C15 H15A 0.9500 . ? C16 C17 1.395(5) . ? C16 C20 1.504(5) . ? C17 C18 1.375(5) . ? C17 H17A 0.9500 . ? C18 C19 1.419(5) . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? 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 C22 Re1 C23 85.31(16) . . ? C22 Re1 C21 86.32(14) . . ? C23 Re1 C21 89.72(15) . . ? C22 Re1 N5 94.15(13) . . ? C23 Re1 N5 170.25(12) . . ? C21 Re1 N5 99.98(13) . . ? C22 Re1 N1 94.31(12) . . ? C23 Re1 N1 93.73(12) . . ? C21 Re1 N1 176.54(12) . . ? N5 Re1 N1 76.59(10) . . ? C22 Re1 N3 174.40(12) . . ? C23 Re1 N3 97.15(13) . . ? C21 Re1 N3 88.66(14) . . ? N5 Re1 N3 84.27(11) . . ? N1 Re1 N3 90.55(11) . . ? C1 N1 N2 106.3(3) . . ? C1 N1 Re1 133.2(2) . . ? N2 N1 Re1 120.43(19) . . ? C3 N2 N1 110.5(3) . . ? C3 N2 C4 127.8(3) . . ? N1 N2 C4 121.7(3) . . ? C11 N3 N4 104.7(3) . . ? C11 N3 Re1 126.1(2) . . ? N4 N3 Re1 122.3(2) . . ? C13 N4 N3 110.6(3) . . ? C13 N4 C14 125.0(3) . . ? N3 N4 C14 123.8(3) . . ? C19 N5 C9 110.9(3) . . ? C19 N5 Re1 123.2(2) . . ? C9 N5 Re1 104.6(2) . . ? N1 C1 C2 109.2(3) . . ? N1 C1 C24 122.7(3) . . ? C2 C1 C24 128.0(3) . . ? C3 C2 C1 106.4(3) . . ? C3 C2 H2A 126.8 . . ? C1 C2 H2A 126.8 . . ? N2 C3 C2 107.5(3) . . ? N2 C3 H3A 126.3 . . ? C2 C3 H3A 126.3 . . ? C5 C4 C9 121.7(3) . . ? C5 C4 N2 119.4(3) . . ? C9 C4 N2 118.8(3) . . ? C4 C5 C6 120.4(3) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C7 C6 C5 118.0(3) . . ? C7 C6 C10 121.9(3) . . ? C5 C6 C10 120.1(3) . . ? C8 C7 C6 121.5(3) . . ? C8 C7 H7A 119.2 . . ? C6 C7 H7A 119.2 . . ? C9 C8 C7 121.1(3) . . ? C9 C8 H8A 119.4 . . ? C7 C8 H8A 119.4 . . ? C8 C9 C4 117.2(3) . . ? C8 C9 N5 122.9(3) . . ? C4 C9 N5 119.9(3) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 110.5(3) . . ? N3 C11 C25 122.9(3) . . ? C12 C11 C25 126.6(3) . . ? C13 C12 C11 106.1(3) . . ? C13 C12 H12A 126.9 . . ? C11 C12 H12A 126.9 . . ? N4 C13 C12 108.1(3) . . ? N4 C13 H13A 125.9 . . ? C12 C13 H13A 125.9 . . ? C15 C14 C19 121.0(3) . . ? C15 C14 N4 117.5(3) . . ? C19 C14 N4 121.3(3) . . ? C16 C15 C14 123.9(3) . . ? C16 C15 H15A 118.1 . . ? C14 C15 H15A 118.1 . . ? C15 C16 C17 115.7(3) . . ? C15 C16 C20 122.1(3) . . ? C17 C16 C20 122.2(3) . . ? C18 C17 C16 122.1(3) . . ? C18 C17 H17A 119.0 . . ? C16 C17 H17A 119.0 . . ? C17 C18 C19 122.9(3) . . ? C17 C18 H18A 118.6 . . ? C19 C18 H18A 118.6 . . ? N5 C19 C14 122.5(3) . . ? N5 C19 C18 123.0(3) . . ? C14 C19 C18 114.4(3) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 Re1 178.5(3) . . ? O2 C22 Re1 177.5(3) . . ? O3 C23 Re1 176.6(3) . . ? C1 C24 H24A 109.5 . . ? C1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C11 C25 H25A 109.5 . . ? C11 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C11 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? 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 C22 Re1 N1 C1 -130.1(3) . . . . ? C23 Re1 N1 C1 -44.6(3) . . . . ? C21 Re1 N1 C1 129.4(19) . . . . ? N5 Re1 N1 C1 136.6(3) . . . . ? N3 Re1 N1 C1 52.6(3) . . . . ? C22 Re1 N1 N2 48.8(3) . . . . ? C23 Re1 N1 N2 134.4(3) . . . . ? C21 Re1 N1 N2 -52(2) . . . . ? N5 Re1 N1 N2 -44.4(2) . . . . ? N3 Re1 N1 N2 -128.4(2) . . . . ? C1 N1 N2 C3 -0.7(4) . . . . ? Re1 N1 N2 C3 -179.9(2) . . . . ? C1 N1 N2 C4 177.9(3) . . . . ? Re1 N1 N2 C4 -1.3(4) . . . . ? C22 Re1 N3 C11 71.9(13) . . . . ? C23 Re1 N3 C11 -44.0(3) . . . . ? C21 Re1 N3 C11 45.6(3) . . . . ? N5 Re1 N3 C11 145.7(3) . . . . ? N1 Re1 N3 C11 -137.8(3) . . . . ? C22 Re1 N3 N4 -74.5(13) . . . . ? C23 Re1 N3 N4 169.7(3) . . . . ? C21 Re1 N3 N4 -100.8(3) . . . . ? N5 Re1 N3 N4 -0.6(2) . . . . ? N1 Re1 N3 N4 75.9(3) . . . . ? C11 N3 N4 C13 0.1(4) . . . . ? Re1 N3 N4 C13 152.5(2) . . . . ? C11 N3 N4 C14 171.1(3) . . . . ? Re1 N3 N4 C14 -36.4(4) . . . . ? C22 Re1 N5 C19 -149.7(3) . . . . ? C23 Re1 N5 C19 -63.2(8) . . . . ? C21 Re1 N5 C19 123.3(3) . . . . ? N1 Re1 N5 C19 -56.3(3) . . . . ? N3 Re1 N5 C19 35.7(3) . . . . ? C22 Re1 N5 C9 -22.2(2) . . . . ? C23 Re1 N5 C9 64.3(8) . . . . ? C21 Re1 N5 C9 -109.1(2) . . . . ? N1 Re1 N5 C9 71.3(2) . . . . ? N3 Re1 N5 C9 163.2(2) . . . . ? N2 N1 C1 C2 0.3(4) . . . . ? Re1 N1 C1 C2 179.4(2) . . . . ? N2 N1 C1 C24 -178.1(3) . . . . ? Re1 N1 C1 C24 1.0(5) . . . . ? N1 C1 C2 C3 0.2(4) . . . . ? C24 C1 C2 C3 178.5(3) . . . . ? N1 N2 C3 C2 0.9(4) . . . . ? C4 N2 C3 C2 -177.7(3) . . . . ? C1 C2 C3 N2 -0.6(4) . . . . ? C3 N2 C4 C5 39.0(5) . . . . ? N1 N2 C4 C5 -139.3(3) . . . . ? C3 N2 C4 C9 -143.2(3) . . . . ? N1 N2 C4 C9 38.4(4) . . . . ? C9 C4 C5 C6 2.3(5) . . . . ? N2 C4 C5 C6 179.9(3) . . . . ? C4 C5 C6 C7 -2.5(5) . . . . ? C4 C5 C6 C10 178.3(3) . . . . ? C5 C6 C7 C8 1.4(5) . . . . ? C10 C6 C7 C8 -179.5(3) . . . . ? C6 C7 C8 C9 0.0(6) . . . . ? C7 C8 C9 C4 -0.3(5) . . . . ? C7 C8 C9 N5 -178.8(3) . . . . ? C5 C4 C9 C8 -0.9(5) . . . . ? N2 C4 C9 C8 -178.5(3) . . . . ? C5 C4 C9 N5 177.7(3) . . . . ? N2 C4 C9 N5 0.1(5) . . . . ? C19 N5 C9 C8 -110.9(4) . . . . ? Re1 N5 C9 C8 114.3(3) . . . . ? C19 N5 C9 C4 70.6(4) . . . . ? Re1 N5 C9 C4 -64.1(3) . . . . ? N4 N3 C11 C12 -0.5(4) . . . . ? Re1 N3 C11 C12 -151.5(3) . . . . ? N4 N3 C11 C25 179.5(3) . . . . ? Re1 N3 C11 C25 28.5(5) . . . . ? N3 C11 C12 C13 0.8(4) . . . . ? C25 C11 C12 C13 -179.2(4) . . . . ? N3 N4 C13 C12 0.4(4) . . . . ? C14 N4 C13 C12 -170.5(3) . . . . ? C11 C12 C13 N4 -0.7(4) . . . . ? C13 N4 C14 C15 30.8(5) . . . . ? N3 N4 C14 C15 -139.0(3) . . . . ? C13 N4 C14 C19 -144.4(3) . . . . ? N3 N4 C14 C19 45.7(4) . . . . ? C19 C14 C15 C16 1.2(5) . . . . ? N4 C14 C15 C16 -174.1(3) . . . . ? C14 C15 C16 C17 0.4(5) . . . . ? C14 C15 C16 C20 -178.4(3) . . . . ? C15 C16 C17 C18 -1.9(5) . . . . ? C20 C16 C17 C18 176.9(3) . . . . ? C16 C17 C18 C19 1.9(5) . . . . ? C9 N5 C19 C14 -164.2(3) . . . . ? Re1 N5 C19 C14 -39.4(4) . . . . ? C9 N5 C19 C18 18.4(4) . . . . ? Re1 N5 C19 C18 143.2(3) . . . . ? C15 C14 C19 N5 -178.8(3) . . . . ? N4 C14 C19 N5 -3.7(5) . . . . ? C15 C14 C19 C18 -1.3(5) . . . . ? N4 C14 C19 C18 173.8(3) . . . . ? C17 C18 C19 N5 177.3(3) . . . . ? C17 C18 C19 C14 -0.2(5) . . . . ? C22 Re1 C21 O1 5(14) . . . . ? C23 Re1 C21 O1 -81(14) . . . . ? N5 Re1 C21 O1 98(14) . . . . ? N1 Re1 C21 O1 105(14) . . . . ? N3 Re1 C21 O1 -178(100) . . . . ? C23 Re1 C22 O2 50(7) . . . . ? C21 Re1 C22 O2 -40(7) . . . . ? N5 Re1 C22 O2 -140(7) . . . . ? N1 Re1 C22 O2 144(7) . . . . ? N3 Re1 C22 O2 -66(7) . . . . ? C22 Re1 C23 O3 52(5) . . . . ? C21 Re1 C23 O3 139(5) . . . . ? N5 Re1 C23 O3 -35(6) . . . . ? N1 Re1 C23 O3 -42(5) . . . . ? N3 Re1 C23 O3 -133(5) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 68.02 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.815 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.098 #===END data_gard8la_3iPr _database_code_depnum_ccdc_archive 'CCDC 806484' #TrackingRef 'Re_Pincer_full.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H30 N5 O3 Re' _chemical_formula_weight 682.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.7528(2) _cell_length_b 13.73050(10) _cell_length_c 13.76030(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.662(1) _cell_angle_gamma 90.00 _cell_volume 2704.79(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8003 _cell_measurement_theta_min 3 _cell_measurement_theta_max 68 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 9.110 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.1847 _exptl_absorpt_correction_T_max 0.6109 _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22830 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0120 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 68.20 _reflns_number_total 4810 _reflns_number_gt 4732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+3.4440P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000107(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4810 _refine_ls_number_parameters 350 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0182 _refine_ls_R_factor_gt 0.0178 _refine_ls_wR_factor_ref 0.0465 _refine_ls_wR_factor_gt 0.0462 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 Re1 Re 0.233286(6) 0.577705(6) 0.341742(7) 0.00999(5) Uani 1 1 d . . . O1 O 0.34728(12) 0.76611(12) 0.41742(14) 0.0218(4) Uani 1 1 d . . . O2 O 0.11457(12) 0.68100(13) 0.13090(13) 0.0232(4) Uani 1 1 d . . . O3 O 0.08834(12) 0.66624(13) 0.41134(14) 0.0228(4) Uani 1 1 d . . . N1 N 0.15520(13) 0.44043(14) 0.29180(15) 0.0122(4) Uani 1 1 d . . . N2 N 0.13391(14) 0.40431(14) 0.19112(15) 0.0138(4) Uani 1 1 d . . . N3 N 0.32997(13) 0.51644(13) 0.49811(15) 0.0119(4) Uani 1 1 d . . . N4 N 0.39658(13) 0.44785(14) 0.50496(15) 0.0126(4) Uani 1 1 d . . . N5 N 0.31297(13) 0.49088(14) 0.27592(15) 0.0126(4) Uani 1 1 d . . . C1 C 0.11669(16) 0.37881(16) 0.33733(18) 0.0145(5) Uani 1 1 d . . . C2 C 0.06997(18) 0.30418(17) 0.2658(2) 0.0201(5) Uani 1 1 d . . . H2A H 0.0365 0.2515 0.2779 0.024 Uiso 1 1 calc R . . C3 C 0.08233(17) 0.32240(18) 0.1748(2) 0.0197(5) Uani 1 1 d . . . H3A H 0.0588 0.2842 0.1114 0.024 Uiso 1 1 calc R . . C4 C 0.16862(16) 0.44756(17) 0.11993(18) 0.0142(4) Uani 1 1 d . . . C5 C 0.11304(17) 0.44675(17) 0.01103(19) 0.0161(5) Uani 1 1 d . . . H5A H 0.0521 0.4195 -0.0153 0.019 Uiso 1 1 calc R . . C6 C 0.14626(17) 0.48588(17) -0.06026(19) 0.0177(5) Uani 1 1 d . . . C7 C 0.23441(17) 0.52874(18) -0.01831(19) 0.0193(5) Uani 1 1 d . . . H7A H 0.2574 0.5575 -0.0654 0.023 Uiso 1 1 calc R . . C8 C 0.28956(16) 0.53017(17) 0.09141(19) 0.0166(5) Uani 1 1 d . . . H8A H 0.3496 0.5595 0.1178 0.020 Uiso 1 1 calc R . . C9 C 0.25822(15) 0.48936(17) 0.16300(17) 0.0137(5) Uani 1 1 d . . . C10 C 0.08807(19) 0.4821(2) -0.17904(19) 0.0246(5) Uani 1 1 d . . . H10A H 0.0911 0.5451 -0.2108 0.037 Uiso 1 1 calc R . . H10B H 0.0231 0.4676 -0.1930 0.037 Uiso 1 1 calc R . . H10C H 0.1121 0.4311 -0.2106 0.037 Uiso 1 1 calc R . . C11 C 0.36192(17) 0.55816(17) 0.59543(19) 0.0157(5) Uani 1 1 d . . . C12 C 0.44730(16) 0.51732(17) 0.66301(18) 0.0168(5) Uani 1 1 d . . . H12A H 0.4842 0.5339 0.7356 0.020 Uiso 1 1 calc R . . C13 C 0.46716(16) 0.44875(17) 0.60367(18) 0.0158(4) Uani 1 1 d . . . H13A H 0.5212 0.4087 0.6277 0.019 Uiso 1 1 calc R . . C14 C 0.38426(15) 0.37607(16) 0.42531(18) 0.0137(4) Uani 1 1 d . . . C15 C 0.41532(16) 0.28240(17) 0.46336(19) 0.0162(5) Uani 1 1 d . . . H15A H 0.4374 0.2699 0.5378 0.019 Uiso 1 1 calc R . . C16 C 0.41489(16) 0.20714(17) 0.3961(2) 0.0183(5) Uani 1 1 d . . . C17 C 0.38182(17) 0.22902(18) 0.2879(2) 0.0205(5) Uani 1 1 d . . . H17A H 0.3820 0.1798 0.2395 0.025 Uiso 1 1 calc R . . C18 C 0.34860(16) 0.32070(17) 0.24900(19) 0.0171(5) Uani 1 1 d . . . H18A H 0.3258 0.3318 0.1742 0.021 Uiso 1 1 calc R . . C19 C 0.34694(15) 0.39880(17) 0.31538(18) 0.0132(4) Uani 1 1 d . . . C20 C 0.44883(19) 0.10672(19) 0.4393(2) 0.0264(6) Uani 1 1 d . . . H20A H 0.4659 0.0710 0.3885 0.040 Uiso 0.50 1 calc PR . . H20B H 0.3991 0.0717 0.4498 0.040 Uiso 0.50 1 calc PR . . H20C H 0.5036 0.1123 0.5079 0.040 Uiso 0.50 1 calc PR . . H20D H 0.4464 0.0990 0.5090 0.040 Uiso 0.50 1 calc PR . . H20E H 0.5133 0.0983 0.4477 0.040 Uiso 0.50 1 calc PR . . H20F H 0.4088 0.0577 0.3895 0.040 Uiso 0.50 1 calc PR . . C21 C 0.30552(16) 0.69523(16) 0.38688(17) 0.0140(4) Uani 1 1 d . . . C22 C 0.15955(16) 0.64002(16) 0.20848(19) 0.0150(5) Uani 1 1 d . . . C23 C 0.14502(16) 0.63390(16) 0.38875(18) 0.0148(5) Uani 1 1 d . . . C24 C 0.12758(16) 0.39296(17) 0.45032(18) 0.0159(5) Uani 1 1 d . . . H24A H 0.1535 0.4596 0.4742 0.019 Uiso 1 1 calc R . . C25 C 0.03323(17) 0.38576(19) 0.4570(2) 0.0218(5) Uani 1 1 d . . . H25A H -0.0095 0.4347 0.4099 0.033 Uiso 1 1 calc R . . H25B H 0.0419 0.3974 0.5308 0.033 Uiso 1 1 calc R . . H25C H 0.0069 0.3206 0.4345 0.033 Uiso 1 1 calc R . . C26 C 0.19641(18) 0.3188(2) 0.5245(2) 0.0252(5) Uani 1 1 d . . . H26A H 0.2574 0.3271 0.5223 0.038 Uiso 1 1 calc R . . H26B H 0.1732 0.2528 0.5010 0.038 Uiso 1 1 calc R . . H26C H 0.2028 0.3288 0.5977 0.038 Uiso 1 1 calc R . . C27 C 0.31129(16) 0.63775(17) 0.62590(18) 0.0170(5) Uani 1 1 d . . . H27A H 0.2658 0.6691 0.5587 0.020 Uiso 1 1 calc R . . C28 C 0.37986(18) 0.71582(18) 0.6935(2) 0.0236(5) Uani 1 1 d . . . H28A H 0.4165 0.7397 0.6558 0.035 Uiso 1 1 calc R . . H28B H 0.4219 0.6878 0.7623 0.035 Uiso 1 1 calc R . . H28C H 0.3451 0.7700 0.7059 0.035 Uiso 1 1 calc R . . C29 C 0.25648(19) 0.59397(19) 0.6846(2) 0.0240(5) Uani 1 1 d . . . H29A H 0.2131 0.5445 0.6393 0.036 Uiso 1 1 calc R . . H29B H 0.2212 0.6455 0.7007 0.036 Uiso 1 1 calc R . . H29C H 0.3000 0.5639 0.7514 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.00940(7) 0.00938(7) 0.01064(7) 0.00065(3) 0.00363(5) 0.00007(3) O1 0.0242(9) 0.0172(9) 0.0217(9) -0.0022(7) 0.0072(7) -0.0071(7) O2 0.0259(10) 0.0202(9) 0.0174(9) 0.0049(7) 0.0030(7) 0.0066(7) O3 0.0199(9) 0.0268(9) 0.0250(9) 0.0026(7) 0.0126(8) 0.0071(7) N1 0.0118(10) 0.0116(9) 0.0123(9) -0.0003(7) 0.0042(8) -0.0004(7) N2 0.0133(10) 0.0147(9) 0.0133(9) -0.0014(7) 0.0056(8) -0.0012(7) N3 0.0107(9) 0.0117(9) 0.0128(9) 0.0015(7) 0.0044(7) 0.0017(7) N4 0.0114(9) 0.0123(9) 0.0137(9) 0.0012(7) 0.0048(8) 0.0011(7) N5 0.0119(9) 0.0137(9) 0.0127(9) -0.0007(7) 0.0057(7) 0.0007(7) C1 0.0121(11) 0.0130(11) 0.0174(11) 0.0018(9) 0.0052(9) 0.0003(8) C2 0.0233(13) 0.0156(11) 0.0243(12) -0.0019(10) 0.0127(10) -0.0072(9) C3 0.0204(13) 0.0177(12) 0.0214(12) -0.0063(10) 0.0091(10) -0.0059(9) C4 0.0146(12) 0.0131(10) 0.0163(11) 0.0001(9) 0.0077(9) 0.0026(9) C5 0.0138(12) 0.0156(11) 0.0169(12) -0.0009(9) 0.0043(9) 0.0019(9) C6 0.0200(12) 0.0172(11) 0.0143(11) 0.0004(9) 0.0057(9) 0.0051(9) C7 0.0215(13) 0.0227(13) 0.0167(12) 0.0032(9) 0.0110(10) 0.0024(10) C8 0.0137(11) 0.0187(12) 0.0187(12) 0.0001(9) 0.0079(9) -0.0008(9) C9 0.0147(12) 0.0122(11) 0.0129(11) -0.0010(8) 0.0046(9) 0.0024(8) C10 0.0250(14) 0.0306(14) 0.0146(12) 0.0026(10) 0.0049(10) 0.0021(11) C11 0.0164(12) 0.0153(11) 0.0162(12) -0.0015(9) 0.0077(10) -0.0037(9) C12 0.0152(12) 0.0211(12) 0.0128(11) 0.0007(9) 0.0046(9) -0.0016(9) C13 0.0125(11) 0.0174(11) 0.0155(11) 0.0023(9) 0.0038(9) 0.0000(9) C14 0.0101(11) 0.0140(11) 0.0170(11) -0.0020(9) 0.0057(9) 0.0000(8) C15 0.0118(11) 0.0154(11) 0.0182(11) 0.0030(9) 0.0031(9) 0.0005(9) C16 0.0134(12) 0.0135(11) 0.0256(12) -0.0004(9) 0.0057(10) 0.0022(9) C17 0.0166(12) 0.0189(12) 0.0227(12) -0.0061(10) 0.0049(10) 0.0026(9) C18 0.0122(11) 0.0206(12) 0.0157(11) -0.0028(9) 0.0030(9) 0.0010(9) C19 0.0085(11) 0.0149(11) 0.0154(11) 0.0000(9) 0.0041(9) -0.0014(8) C20 0.0265(14) 0.0154(12) 0.0321(14) -0.0005(11) 0.0072(11) 0.0036(10) C21 0.0138(11) 0.0159(11) 0.0125(10) 0.0017(9) 0.0057(9) 0.0019(9) C22 0.0152(11) 0.0117(10) 0.0181(12) -0.0023(9) 0.0072(9) -0.0018(9) C23 0.0153(12) 0.0130(11) 0.0138(11) 0.0029(9) 0.0038(9) -0.0002(9) C24 0.0182(12) 0.0139(11) 0.0152(11) 0.0012(9) 0.0065(9) -0.0036(9) C25 0.0207(13) 0.0264(13) 0.0197(12) 0.0006(10) 0.0099(10) -0.0001(10) C26 0.0217(13) 0.0288(14) 0.0251(13) 0.0097(11) 0.0097(11) 0.0014(11) C27 0.0174(12) 0.0202(12) 0.0132(11) -0.0007(9) 0.0060(9) 0.0029(9) C28 0.0277(14) 0.0200(12) 0.0262(13) -0.0061(10) 0.0144(11) -0.0021(10) C29 0.0234(14) 0.0243(13) 0.0291(14) -0.0050(11) 0.0156(12) -0.0025(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C22 1.915(2) . ? Re1 C21 1.922(2) . ? Re1 C23 1.923(2) . ? Re1 N5 2.1831(18) . ? Re1 N1 2.1984(19) . ? Re1 N3 2.2186(18) . ? O1 C21 1.151(3) . ? O2 C22 1.152(3) . ? O3 C23 1.150(3) . ? N1 C1 1.339(3) . ? N1 N2 1.375(3) . ? N2 C3 1.350(3) . ? N2 C4 1.435(3) . ? N3 C11 1.346(3) . ? N3 N4 1.384(3) . ? N4 C13 1.349(3) . ? N4 C14 1.426(3) . ? N5 C19 1.392(3) . ? N5 C9 1.428(3) . ? C1 C2 1.399(3) . ? C1 C24 1.504(3) . ? C2 C3 1.368(4) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C5 1.385(3) . ? C4 C9 1.405(3) . ? C5 C6 1.398(3) . ? C5 H5A 0.9500 . ? C6 C7 1.392(4) . ? C6 C10 1.505(3) . ? C7 C8 1.393(3) . ? C7 H7A 0.9500 . ? C8 C9 1.391(3) . ? C8 H8A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.395(3) . ? C11 C27 1.512(3) . ? C12 C13 1.365(3) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.398(3) . ? C14 C19 1.410(3) . ? C15 C16 1.386(3) . ? C15 H15A 0.9500 . ? C16 C17 1.389(4) . ? C16 C20 1.509(3) . ? C17 C18 1.382(3) . ? C17 H17A 0.9500 . ? C18 C19 1.416(3) . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C20 H20D 0.9800 . ? C20 H20E 0.9800 . ? C20 H20F 0.9800 . ? C24 C26 1.527(3) . ? C24 C25 1.530(3) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C29 1.530(3) . ? C27 C28 1.531(3) . ? C27 H27A 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? 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 C22 Re1 C21 88.57(9) . . ? C22 Re1 C23 84.72(9) . . ? C21 Re1 C23 88.17(9) . . ? C22 Re1 N5 94.06(8) . . ? C21 Re1 N5 103.13(8) . . ? C23 Re1 N5 168.61(8) . . ? C22 Re1 N1 92.70(8) . . ? C21 Re1 N1 178.02(8) . . ? C23 Re1 N1 93.46(8) . . ? N5 Re1 N1 75.27(7) . . ? C22 Re1 N3 174.18(8) . . ? C21 Re1 N3 86.02(8) . . ? C23 Re1 N3 97.24(8) . . ? N5 Re1 N3 85.09(7) . . ? N1 Re1 N3 92.65(7) . . ? C1 N1 N2 106.02(18) . . ? C1 N1 Re1 134.35(16) . . ? N2 N1 Re1 119.59(14) . . ? C3 N2 N1 110.19(19) . . ? C3 N2 C4 127.2(2) . . ? N1 N2 C4 122.45(19) . . ? C11 N3 N4 105.29(18) . . ? C11 N3 Re1 128.59(15) . . ? N4 N3 Re1 121.23(13) . . ? C13 N4 N3 110.20(18) . . ? C13 N4 C14 124.80(19) . . ? N3 N4 C14 124.20(18) . . ? C19 N5 C9 111.74(18) . . ? C19 N5 Re1 121.89(14) . . ? C9 N5 Re1 105.58(13) . . ? N1 C1 C2 110.0(2) . . ? N1 C1 C24 121.6(2) . . ? C2 C1 C24 128.5(2) . . ? C3 C2 C1 106.0(2) . . ? C3 C2 H2A 127.0 . . ? C1 C2 H2A 127.0 . . ? N2 C3 C2 107.8(2) . . ? N2 C3 H3A 126.1 . . ? C2 C3 H3A 126.1 . . ? C5 C4 C9 122.0(2) . . ? C5 C4 N2 119.1(2) . . ? C9 C4 N2 118.9(2) . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C7 C6 C5 118.2(2) . . ? C7 C6 C10 121.0(2) . . ? C5 C6 C10 120.8(2) . . ? C6 C7 C8 121.2(2) . . ? C6 C7 H7A 119.4 . . ? C8 C7 H7A 119.4 . . ? C9 C8 C7 121.1(2) . . ? C9 C8 H8A 119.4 . . ? C7 C8 H8A 119.4 . . ? C8 C9 C4 117.2(2) . . ? C8 C9 N5 122.2(2) . . ? C4 C9 N5 120.6(2) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 110.4(2) . . ? N3 C11 C27 124.2(2) . . ? C12 C11 C27 125.4(2) . . ? C13 C12 C11 106.0(2) . . ? C13 C12 H12A 127.0 . . ? C11 C12 H12A 127.0 . . ? N4 C13 C12 108.1(2) . . ? N4 C13 H13A 126.0 . . ? C12 C13 H13A 126.0 . . ? C15 C14 C19 122.0(2) . . ? C15 C14 N4 115.7(2) . . ? C19 C14 N4 122.2(2) . . ? C16 C15 C14 122.2(2) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C15 C16 C17 116.7(2) . . ? C15 C16 C20 121.1(2) . . ? C17 C16 C20 122.2(2) . . ? C18 C17 C16 121.6(2) . . ? C18 C17 H17A 119.2 . . ? C16 C17 H17A 119.2 . . ? C17 C18 C19 123.1(2) . . ? C17 C18 H18A 118.5 . . ? C19 C18 H18A 118.5 . . ? N5 C19 C14 122.7(2) . . ? N5 C19 C18 123.0(2) . . ? C14 C19 C18 114.4(2) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C20 H20D 109.5 . . ? H20A C20 H20D 141.1 . . ? H20B C20 H20D 56.3 . . ? H20C C20 H20D 56.3 . . ? C16 C20 H20E 109.5 . . ? H20A C20 H20E 56.3 . . ? H20B C20 H20E 141.1 . . ? H20C C20 H20E 56.3 . . ? H20D C20 H20E 109.5 . . ? C16 C20 H20F 109.5 . . ? H20A C20 H20F 56.3 . . ? H20B C20 H20F 56.3 . . ? H20C C20 H20F 141.1 . . ? H20D C20 H20F 109.5 . . ? H20E C20 H20F 109.5 . . ? O1 C21 Re1 176.9(2) . . ? O2 C22 Re1 176.9(2) . . ? O3 C23 Re1 176.2(2) . . ? C1 C24 C26 110.3(2) . . ? C1 C24 C25 111.04(19) . . ? C26 C24 C25 110.7(2) . . ? C1 C24 H24A 108.2 . . ? C26 C24 H24A 108.2 . . ? C25 C24 H24A 108.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C11 C27 C29 110.0(2) . . ? C11 C27 C28 110.8(2) . . ? C29 C27 C28 111.4(2) . . ? C11 C27 H27A 108.2 . . ? C29 C27 H27A 108.2 . . ? C28 C27 H27A 108.2 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? 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 C22 Re1 N1 C1 -132.8(2) . . . . ? C21 Re1 N1 C1 98(2) . . . . ? C23 Re1 N1 C1 -47.9(2) . . . . ? N5 Re1 N1 C1 133.7(2) . . . . ? N3 Re1 N1 C1 49.5(2) . . . . ? C22 Re1 N1 N2 44.22(17) . . . . ? C21 Re1 N1 N2 -85(2) . . . . ? C23 Re1 N1 N2 129.09(16) . . . . ? N5 Re1 N1 N2 -49.27(15) . . . . ? N3 Re1 N1 N2 -133.49(16) . . . . ? C1 N1 N2 C3 0.6(2) . . . . ? Re1 N1 N2 C3 -177.14(15) . . . . ? C1 N1 N2 C4 -175.9(2) . . . . ? Re1 N1 N2 C4 6.4(3) . . . . ? C22 Re1 N3 C11 65.8(8) . . . . ? C21 Re1 N3 C11 44.0(2) . . . . ? C23 Re1 N3 C11 -43.6(2) . . . . ? N5 Re1 N3 C11 147.6(2) . . . . ? N1 Re1 N3 C11 -137.44(19) . . . . ? C22 Re1 N3 N4 -85.7(8) . . . . ? C21 Re1 N3 N4 -107.43(16) . . . . ? C23 Re1 N3 N4 164.92(16) . . . . ? N5 Re1 N3 N4 -3.87(15) . . . . ? N1 Re1 N3 N4 71.09(16) . . . . ? C11 N3 N4 C13 -0.4(2) . . . . ? Re1 N3 N4 C13 156.79(15) . . . . ? C11 N3 N4 C14 169.7(2) . . . . ? Re1 N3 N4 C14 -33.0(3) . . . . ? C22 Re1 N5 C19 -148.61(17) . . . . ? C21 Re1 N5 C19 121.92(17) . . . . ? C23 Re1 N5 C19 -65.2(5) . . . . ? N1 Re1 N5 C19 -56.88(17) . . . . ? N3 Re1 N5 C19 37.17(17) . . . . ? C22 Re1 N5 C9 -19.83(15) . . . . ? C21 Re1 N5 C9 -109.31(15) . . . . ? C23 Re1 N5 C9 63.6(4) . . . . ? N1 Re1 N5 C9 71.90(14) . . . . ? N3 Re1 N5 C9 165.95(15) . . . . ? N2 N1 C1 C2 -0.7(3) . . . . ? Re1 N1 C1 C2 176.59(17) . . . . ? N2 N1 C1 C24 178.23(19) . . . . ? Re1 N1 C1 C24 -4.5(3) . . . . ? N1 C1 C2 C3 0.5(3) . . . . ? C24 C1 C2 C3 -178.3(2) . . . . ? N1 N2 C3 C2 -0.3(3) . . . . ? C4 N2 C3 C2 176.0(2) . . . . ? C1 C2 C3 N2 -0.1(3) . . . . ? C3 N2 C4 C5 38.2(3) . . . . ? N1 N2 C4 C5 -145.9(2) . . . . ? C3 N2 C4 C9 -141.7(2) . . . . ? N1 N2 C4 C9 34.2(3) . . . . ? C9 C4 C5 C6 1.7(4) . . . . ? N2 C4 C5 C6 -178.2(2) . . . . ? C4 C5 C6 C7 -2.6(3) . . . . ? C4 C5 C6 C10 177.7(2) . . . . ? C5 C6 C7 C8 2.0(4) . . . . ? C10 C6 C7 C8 -178.3(2) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C7 C8 C9 C4 -0.5(3) . . . . ? C7 C8 C9 N5 -179.3(2) . . . . ? C5 C4 C9 C8 -0.2(3) . . . . ? N2 C4 C9 C8 179.7(2) . . . . ? C5 C4 C9 N5 178.6(2) . . . . ? N2 C4 C9 N5 -1.5(3) . . . . ? C19 N5 C9 C8 -108.8(2) . . . . ? Re1 N5 C9 C8 116.7(2) . . . . ? C19 N5 C9 C4 72.5(3) . . . . ? Re1 N5 C9 C4 -62.0(2) . . . . ? N4 N3 C11 C12 0.2(2) . . . . ? Re1 N3 C11 C12 -154.76(16) . . . . ? N4 N3 C11 C27 -179.6(2) . . . . ? Re1 N3 C11 C27 25.4(3) . . . . ? N3 C11 C12 C13 0.1(3) . . . . ? C27 C11 C12 C13 179.9(2) . . . . ? N3 N4 C13 C12 0.5(3) . . . . ? C14 N4 C13 C12 -169.6(2) . . . . ? C11 C12 C13 N4 -0.4(3) . . . . ? C13 N4 C14 C15 31.8(3) . . . . ? N3 N4 C14 C15 -137.0(2) . . . . ? C13 N4 C14 C19 -145.6(2) . . . . ? N3 N4 C14 C19 45.7(3) . . . . ? C19 C14 C15 C16 2.7(4) . . . . ? N4 C14 C15 C16 -174.7(2) . . . . ? C14 C15 C16 C17 -0.1(3) . . . . ? C14 C15 C16 C20 180.0(2) . . . . ? C15 C16 C17 C18 -1.7(4) . . . . ? C20 C16 C17 C18 178.2(2) . . . . ? C16 C17 C18 C19 1.0(4) . . . . ? C9 N5 C19 C14 -165.2(2) . . . . ? Re1 N5 C19 C14 -39.1(3) . . . . ? C9 N5 C19 C18 16.1(3) . . . . ? Re1 N5 C19 C18 142.13(18) . . . . ? C15 C14 C19 N5 177.9(2) . . . . ? N4 C14 C19 N5 -5.0(3) . . . . ? C15 C14 C19 C18 -3.2(3) . . . . ? N4 C14 C19 C18 173.9(2) . . . . ? C17 C18 C19 N5 -179.6(2) . . . . ? C17 C18 C19 C14 1.5(3) . . . . ? C22 Re1 C21 O1 115(4) . . . . ? C23 Re1 C21 O1 30(4) . . . . ? N5 Re1 C21 O1 -151(4) . . . . ? N1 Re1 C21 O1 -116(4) . . . . ? N3 Re1 C21 O1 -67(4) . . . . ? C21 Re1 C22 O2 -52(4) . . . . ? C23 Re1 C22 O2 36(4) . . . . ? N5 Re1 C22 O2 -155(4) . . . . ? N1 Re1 C22 O2 129(4) . . . . ? N3 Re1 C22 O2 -74(4) . . . . ? C22 Re1 C23 O3 40(3) . . . . ? C21 Re1 C23 O3 129(3) . . . . ? N5 Re1 C23 O3 -44(3) . . . . ? N1 Re1 C23 O3 -52(3) . . . . ? N3 Re1 C23 O3 -146(3) . . . . ? N1 C1 C24 C26 -105.9(2) . . . . ? C2 C1 C24 C26 72.9(3) . . . . ? N1 C1 C24 C25 131.0(2) . . . . ? C2 C1 C24 C25 -50.3(3) . . . . ? N3 C11 C27 C29 97.9(3) . . . . ? C12 C11 C27 C29 -81.9(3) . . . . ? N3 C11 C27 C28 -138.5(2) . . . . ? C12 C11 C27 C28 41.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 68.20 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.578 _refine_diff_density_min -0.606 _refine_diff_density_rms 0.071 #===END data_gard10n_4iPr _database_code_depnum_ccdc_archive 'CCDC 806485' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C30 H33 N5 O3 Re, 2(C H2 Cl2), I' _chemical_formula_sum 'C32 H37 Cl4 I N5 O3 Re' _chemical_formula_weight 994.57 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' _space_group_IT_number 2 _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_angle_alpha 73.5426(18) _cell_angle_beta 85.7981(19) _cell_angle_gamma 65.475(2) _cell_formula_units_Z 2 _cell_length_a 10.9417(3) _cell_length_b 12.1830(2) _cell_length_c 15.7817(3) _cell_measurement_reflns_used 38198 _cell_measurement_temperature 100 _cell_measurement_theta_max 32.7208 _cell_measurement_theta_min 3.2954 _cell_volume 1833.16(7) _exptl_absorpt_coefficient_mu 4.487 _exptl_absorpt_correction_T_max 0.866 _exptl_absorpt_correction_T_min 0.349 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_crystal_F_000 968 _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_size_max 0.3303 _exptl_crystal_size_mid 0.0662 _exptl_crystal_size_min 0.0392 _exptl_special_details ? _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean 10.3756 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -14.00 98.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - 19.7635 77.0000 150.0000 112 #__ type_ start__ end____ width___ exp.time_ 2 omega -12.00 82.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - 19.7635 67.0000 -46.0000 94 #__ type_ start__ end____ width___ exp.time_ 3 omega -28.00 51.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - 19.7635 -67.0000 0.0000 79 #__ type_ start__ end____ width___ exp.time_ 4 omega 15.00 42.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - 19.7635 -37.0000 150.0000 27 #__ type_ start__ end____ width___ exp.time_ 5 omega 12.00 93.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - 19.7635 0.0000 150.0000 81 #__ type_ start__ end____ width___ exp.time_ 6 omega -7.00 96.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - 19.7635 37.0000 90.0000 103 #__ type_ start__ end____ width___ exp.time_ 7 omega -56.00 46.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - 19.7635 -37.0000 120.0000 102 #__ type_ start__ end____ width___ exp.time_ 8 omega -56.00 46.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - 19.7635 -37.0000 30.0000 102 #__ type_ start__ end____ width___ exp.time_ 9 omega -95.00 12.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - -19.9198 -67.0000 -133.0000 107 #__ type_ start__ end____ width___ exp.time_ 10 omega -54.00 59.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - -19.9198 77.0000 120.0000 113 #__ type_ start__ end____ width___ exp.time_ 11 omega -54.00 -29.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - -19.9198 77.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 12 omega -54.00 59.00 1.0000 19.9700 omega____ theta____ kappa____ phi______ frames - -19.9198 77.0000 -90.0000 113 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0655779 _diffrn_orient_matrix_UB_12 0.028576 _diffrn_orient_matrix_UB_13 0.0146139 _diffrn_orient_matrix_UB_21 0.0269183 _diffrn_orient_matrix_UB_22 0.0143438 _diffrn_orient_matrix_UB_23 0.0328831 _diffrn_orient_matrix_UB_31 -0.0080773 _diffrn_orient_matrix_UB_32 0.058462 _diffrn_orient_matrix_UB_33 -0.0301181 _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 59279 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 32.79 _diffrn_reflns_theta_min 3.30 _reflns_number_gt 11250 _reflns_number_total 12747 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.006 _refine_diff_density_min -0.896 _refine_diff_density_rms 0.104 _refine_ls_R_factor_all 0.0241 _refine_ls_R_factor_gt 0.0191 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 422 _refine_ls_number_reflns 12747 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.0463 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.549765(7) 0.056184(6) 0.672380(4) 0.00956(2) Uani 1 1 d . . . O1 O 0.34723(15) -0.05883(13) 0.67424(9) 0.0220(3) Uani 1 1 d . . . O2 O 0.68947(16) -0.04975(14) 0.52021(9) 0.0243(3) Uani 1 1 d . . . O3 O 0.39279(15) 0.28412(12) 0.51735(9) 0.0208(3) Uani 1 1 d . . . N1 N 0.69683(15) 0.12409(13) 0.69408(9) 0.0105(3) Uani 1 1 d . . . N2 N 0.65243(15) 0.23825(13) 0.71100(10) 0.0122(3) Uani 1 1 d . . . N3 N 0.65749(16) -0.10798(13) 0.78231(9) 0.0117(3) Uani 1 1 d . . . N4 N 0.69226(16) -0.10392(13) 0.86306(9) 0.0122(3) Uani 1 1 d . . . N5 N 0.45760(15) 0.14848(13) 0.78418(9) 0.0111(3) Uani 1 1 d . . . C1 C 0.82995(18) 0.06837(16) 0.71324(11) 0.0117(3) Uani 1 1 d . . . C2 C 0.87010(19) 0.14611(17) 0.74428(12) 0.0148(3) Uani 1 1 d . . . H2 H 0.9585 0.1290 0.7627 0.018 Uiso 1 1 calc R . . C3 C 0.75508(19) 0.25209(17) 0.74259(12) 0.0144(3) Uani 1 1 d . . . H3 H 0.7489 0.3224 0.7604 0.017 Uiso 1 1 calc R . . C4 C 0.51454(18) 0.32324(16) 0.69906(11) 0.0122(3) Uani 1 1 d . . . C5 C 0.4812(2) 0.44753(17) 0.65197(12) 0.0151(3) Uani 1 1 d . . . H5 H 0.5501 0.4730 0.6269 0.018 Uiso 1 1 calc R . . C6 C 0.3476(2) 0.53568(17) 0.64090(12) 0.0167(4) Uani 1 1 d . . . C7 C 0.2498(2) 0.49460(17) 0.67831(12) 0.0170(4) Uani 1 1 d . . . H7 H 0.1584 0.5535 0.6720 0.020 Uiso 1 1 calc R . . C8 C 0.28170(19) 0.36945(17) 0.72489(11) 0.0141(3) Uani 1 1 d . . . H8 H 0.2124 0.3440 0.7491 0.017 Uiso 1 1 calc R . . C9 C 0.41471(18) 0.28227(16) 0.73580(11) 0.0117(3) Uani 1 1 d . . . C10 C 0.3127(2) 0.67131(18) 0.59166(16) 0.0271(5) Uani 1 1 d . . . H10B H 0.3855 0.6772 0.5532 0.041 Uiso 1 1 calc R . . H10C H 0.3007 0.7197 0.6341 0.041 Uiso 1 1 calc R . . H10A H 0.2290 0.7052 0.5556 0.041 Uiso 1 1 calc R . . C11 C 0.70800(19) -0.23080(16) 0.78554(11) 0.0130(3) Uani 1 1 d . . . C12 C 0.7751(2) -0.30509(17) 0.86761(12) 0.0164(4) Uani 1 1 d . . . H12 H 0.8202 -0.3941 0.8864 0.020 Uiso 1 1 calc R . . C13 C 0.7625(2) -0.22314(17) 0.91520(12) 0.0173(4) Uani 1 1 d . . . H13 H 0.7967 -0.2453 0.9741 0.021 Uiso 1 1 calc R . . C14 C 0.66203(19) 0.00635(16) 0.88978(11) 0.0120(3) Uani 1 1 d . . . C15 C 0.75053(19) -0.00418(16) 0.95410(11) 0.0133(3) Uani 1 1 d . . . H15 H 0.8310 -0.0786 0.9709 0.016 Uiso 1 1 calc R . . C16 C 0.7249(2) 0.09067(17) 0.99442(11) 0.0153(3) Uani 1 1 d . . . C17 C 0.6051(2) 0.19786(18) 0.97032(12) 0.0191(4) Uani 1 1 d . . . H17 H 0.5820 0.2613 0.9998 0.023 Uiso 1 1 calc R . . C18 C 0.5198(2) 0.21243(17) 0.90361(12) 0.0171(4) Uani 1 1 d . . . H18 H 0.4396 0.2871 0.8869 0.021 Uiso 1 1 calc R . . C19 C 0.54884(19) 0.11985(16) 0.86021(11) 0.0127(3) Uani 1 1 d . . . C20 C 0.8253(2) 0.07728(19) 1.06089(13) 0.0204(4) Uani 1 1 d . . . H20C H 0.7778 0.1186 1.1059 0.031 Uiso 1 1 calc R . . H20A H 0.8848 0.1165 1.0309 0.031 Uiso 1 1 calc R . . H20B H 0.8789 -0.0120 1.0892 0.031 Uiso 1 1 calc R . . C21 C 0.91630(18) -0.05612(16) 0.69684(11) 0.0134(3) Uani 1 1 d . . . H21 H 0.8583 -0.1020 0.6986 0.016 Uiso 1 1 calc R . . C22 C 0.9711(2) -0.0348(2) 0.60468(13) 0.0235(4) Uani 1 1 d . . . H22C H 1.0328 0.0055 0.6025 0.035 Uiso 1 1 calc R . . H22A H 0.8964 0.0194 0.5608 0.035 Uiso 1 1 calc R . . H22B H 1.0193 -0.1157 0.5916 0.035 Uiso 1 1 calc R . . C23 C 1.0305(2) -0.13732(19) 0.76733(14) 0.0247(4) Uani 1 1 d . . . H23B H 0.9932 -0.1473 0.8260 0.037 Uiso 1 1 calc R . . H23C H 1.0922 -0.0968 0.7642 0.037 Uiso 1 1 calc R . . H23A H 1.0793 -0.2200 0.7571 0.037 Uiso 1 1 calc R . . C24 C 0.6997(2) -0.27930(17) 0.70936(12) 0.0155(3) Uani 1 1 d . . . H24 H 0.6394 -0.2073 0.6611 0.019 Uiso 1 1 calc R . . C25 C 0.6401(2) -0.37713(19) 0.73789(14) 0.0237(4) Uani 1 1 d . . . H25B H 0.5503 -0.3393 0.7597 0.036 Uiso 1 1 calc R . . H25C H 0.6984 -0.4486 0.7850 0.036 Uiso 1 1 calc R . . H25A H 0.6334 -0.4061 0.6872 0.036 Uiso 1 1 calc R . . C26 C 0.8396(2) -0.33619(19) 0.67358(13) 0.0217(4) Uani 1 1 d . . . H26C H 0.8982 -0.4103 0.7190 0.033 Uiso 1 1 calc R . . H26B H 0.8782 -0.2739 0.6580 0.033 Uiso 1 1 calc R . . H26A H 0.8318 -0.3607 0.6209 0.033 Uiso 1 1 calc R . . C27 C 0.34225(19) 0.11637(18) 0.82092(12) 0.0163(3) Uani 1 1 d . . . H27C H 0.2964 0.1655 0.8623 0.024 Uiso 1 1 calc R . . H27B H 0.3763 0.0266 0.8520 0.024 Uiso 1 1 calc R . . H27A H 0.2788 0.1361 0.7724 0.024 Uiso 1 1 calc R . . C28 C 0.42048(19) -0.01256(16) 0.67065(11) 0.0141(3) Uani 1 1 d . . . C29 C 0.6382(2) -0.01227(17) 0.57884(11) 0.0148(3) Uani 1 1 d . . . C30 C 0.44977(19) 0.20065(17) 0.57719(12) 0.0139(3) Uani 1 1 d . . . I1 I 0.979793(12) 0.317292(10) 0.878506(7) 0.01449(3) Uani 1 1 d . . . Cl1 Cl 1.11226(6) 0.22653(5) 0.59710(4) 0.03057(12) Uani 1 1 d . . . Cl2 Cl 0.84914(6) 0.43477(5) 0.54590(3) 0.02738(11) Uani 1 1 d . . . C1S C 0.9968(2) 0.36948(18) 0.61484(13) 0.0198(4) Uani 1 1 d . . . H1SB H 1.0393 0.4297 0.6027 0.024 Uiso 1 1 calc R . . H1SA H 0.9729 0.3549 0.6775 0.024 Uiso 1 1 calc R . . Cl3 Cl 0.39335(8) 0.57469(7) 0.88249(5) 0.04451(16) Uani 1 1 d . . . Cl4 Cl 0.16602(6) 0.50344(5) 0.91170(3) 0.02680(11) Uani 1 1 d . . . C2S C 0.2638(3) 0.5622(3) 0.95296(17) 0.0379(6) Uani 1 1 d . . . H2SB H 0.3042 0.5058 1.0120 0.045 Uiso 1 1 calc R . . H2SA H 0.2051 0.6460 0.9602 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.00979(3) 0.00976(3) 0.00848(3) -0.00274(2) -0.00062(2) -0.00311(2) O1 0.0223(8) 0.0221(7) 0.0247(7) -0.0037(6) -0.0029(6) -0.0135(6) O2 0.0298(9) 0.0245(7) 0.0153(6) -0.0097(6) 0.0034(6) -0.0058(7) O3 0.0212(8) 0.0171(7) 0.0175(7) 0.0009(5) -0.0050(5) -0.0044(6) N1 0.0110(7) 0.0093(6) 0.0106(6) -0.0032(5) 0.0014(5) -0.0035(5) N2 0.0103(7) 0.0105(7) 0.0161(7) -0.0052(5) 0.0006(5) -0.0036(6) N3 0.0126(7) 0.0117(7) 0.0111(6) -0.0040(5) 0.0003(5) -0.0047(6) N4 0.0160(8) 0.0110(7) 0.0090(6) -0.0031(5) -0.0009(5) -0.0044(6) N5 0.0106(7) 0.0114(7) 0.0100(6) -0.0026(5) 0.0009(5) -0.0038(6) C1 0.0106(8) 0.0128(8) 0.0109(7) -0.0033(6) 0.0016(6) -0.0042(6) C2 0.0108(8) 0.0158(8) 0.0182(8) -0.0046(7) -0.0013(6) -0.0055(7) C3 0.0129(8) 0.0155(8) 0.0174(8) -0.0057(7) 0.0005(6) -0.0075(7) C4 0.0105(8) 0.0121(8) 0.0143(8) -0.0066(6) 0.0001(6) -0.0028(6) C5 0.0153(9) 0.0146(8) 0.0168(8) -0.0060(7) 0.0022(7) -0.0067(7) C6 0.0168(9) 0.0113(8) 0.0198(9) -0.0040(7) -0.0014(7) -0.0036(7) C7 0.0135(9) 0.0153(8) 0.0182(9) -0.0064(7) -0.0005(7) -0.0007(7) C8 0.0121(8) 0.0160(8) 0.0138(8) -0.0057(6) 0.0017(6) -0.0048(7) C9 0.0119(8) 0.0126(8) 0.0103(7) -0.0045(6) 0.0004(6) -0.0038(7) C10 0.0234(11) 0.0140(9) 0.0379(12) -0.0021(8) -0.0012(9) -0.0048(8) C11 0.0149(9) 0.0115(8) 0.0134(8) -0.0045(6) 0.0014(6) -0.0057(7) C12 0.0212(10) 0.0116(8) 0.0145(8) -0.0028(6) -0.0010(7) -0.0051(7) C13 0.0229(10) 0.0129(8) 0.0121(8) -0.0019(6) -0.0035(7) -0.0040(7) C14 0.0148(8) 0.0128(8) 0.0095(7) -0.0037(6) 0.0022(6) -0.0064(7) C15 0.0161(9) 0.0122(8) 0.0102(7) -0.0012(6) -0.0006(6) -0.0056(7) C16 0.0210(10) 0.0169(8) 0.0101(7) -0.0044(6) 0.0003(7) -0.0095(7) C17 0.0259(11) 0.0163(9) 0.0140(8) -0.0079(7) -0.0019(7) -0.0047(8) C18 0.0193(10) 0.0145(8) 0.0138(8) -0.0058(7) -0.0002(7) -0.0022(7) C19 0.0145(8) 0.0150(8) 0.0084(7) -0.0034(6) 0.0006(6) -0.0058(7) C20 0.0272(11) 0.0197(9) 0.0165(9) -0.0055(7) -0.0049(8) -0.0104(8) C21 0.0113(8) 0.0140(8) 0.0139(8) -0.0047(6) 0.0011(6) -0.0037(7) C22 0.0241(11) 0.0233(10) 0.0195(9) -0.0103(8) 0.0084(8) -0.0047(9) C23 0.0193(10) 0.0213(10) 0.0241(10) -0.0060(8) -0.0042(8) 0.0012(8) C24 0.0190(9) 0.0118(8) 0.0155(8) -0.0040(6) -0.0021(7) -0.0056(7) C25 0.0281(12) 0.0194(9) 0.0280(10) -0.0072(8) -0.0024(8) -0.0130(9) C26 0.0252(11) 0.0194(9) 0.0223(9) -0.0127(8) 0.0056(8) -0.0072(8) C27 0.0138(9) 0.0181(9) 0.0168(8) -0.0039(7) 0.0041(7) -0.0076(7) C28 0.0159(9) 0.0134(8) 0.0100(7) -0.0017(6) -0.0024(6) -0.0037(7) C29 0.0170(9) 0.0138(8) 0.0117(8) -0.0024(6) -0.0014(6) -0.0049(7) C30 0.0140(9) 0.0147(8) 0.0149(8) -0.0062(6) 0.0020(6) -0.0066(7) I1 0.01342(6) 0.01394(5) 0.01442(5) -0.00418(4) -0.00013(4) -0.00375(4) Cl1 0.0191(3) 0.0253(3) 0.0429(3) -0.0136(2) 0.0058(2) -0.0030(2) Cl2 0.0235(3) 0.0265(2) 0.0249(2) -0.00353(19) -0.0073(2) -0.0043(2) C1S 0.0196(10) 0.0196(9) 0.0183(9) -0.0057(7) -0.0020(7) -0.0055(8) Cl3 0.0479(4) 0.0537(4) 0.0464(4) -0.0252(3) 0.0278(3) -0.0315(3) Cl4 0.0338(3) 0.0244(2) 0.0215(2) -0.00589(19) 0.0017(2) -0.0118(2) C2S 0.0499(17) 0.0493(15) 0.0376(13) -0.0271(12) 0.0251(12) -0.0367(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 N1 2.1765(15) . ? Re1 N3 2.1854(14) . ? Re1 N5 2.3058(15) . ? Re1 C28 1.9249(19) . ? Re1 C29 1.9051(19) . ? Re1 C30 1.9224(18) . ? O1 C28 1.146(2) . ? O2 C29 1.153(2) . ? O3 C30 1.153(2) . ? N1 N2 1.368(2) . ? N1 C1 1.342(2) . ? N2 C3 1.351(2) . ? N2 C4 1.421(2) . ? N3 N4 1.3761(19) . ? N3 C11 1.350(2) . ? N4 C13 1.366(2) . ? N4 C14 1.423(2) . ? N5 C9 1.474(2) . ? N5 C19 1.486(2) . ? N5 C27 1.502(2) . ? C1 C2 1.403(2) . ? C1 C21 1.502(2) . ? C2 H2 0.9500 . ? C2 C3 1.374(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(2) . ? C4 C9 1.405(3) . ? C5 H5 0.9500 . ? C5 C6 1.396(3) . ? C6 C7 1.389(3) . ? C6 C10 1.507(3) . ? C7 H7 0.9500 . ? C7 C8 1.396(3) . ? C8 H8 0.9500 . ? C8 C9 1.388(2) . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 H10A 0.9800 . ? C11 C12 1.400(2) . ? C11 C24 1.505(2) . ? C12 H12 0.9500 . ? C12 C13 1.370(2) . ? C13 H13 0.9500 . ? C14 C15 1.397(2) . ? C14 C19 1.400(2) . ? C15 H15 0.9500 . ? C15 C16 1.393(2) . ? C16 C17 1.392(3) . ? C16 C20 1.502(3) . ? C17 H17 0.9500 . ? C17 C18 1.383(3) . ? C18 H18 0.9500 . ? C18 C19 1.397(2) . ? C20 H20C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C21 H21 1.0000 . ? C21 C22 1.526(3) . ? C21 C23 1.527(3) . ? C22 H22C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C23 H23A 0.9800 . ? C24 H24 1.0000 . ? C24 C25 1.532(3) . ? C24 C26 1.536(3) . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C25 H25A 0.9800 . ? C26 H26C 0.9800 . ? C26 H26B 0.9800 . ? C26 H26A 0.9800 . ? C27 H27C 0.9800 . ? C27 H27B 0.9800 . ? C27 H27A 0.9800 . ? Cl1 C1S 1.762(2) . ? Cl2 C1S 1.769(2) . ? C1S H1SB 0.9900 . ? C1S H1SA 0.9900 . ? Cl3 C2S 1.767(3) . ? Cl4 C2S 1.756(3) . ? C2S H2SB 0.9900 . ? C2S H2SA 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 O1 C28 Re1 175.89(15) . . ? O2 C29 Re1 177.67(17) . . ? O3 C30 Re1 176.80(16) . . ? N1 Re1 N3 85.76(5) . . ? N1 Re1 N5 78.25(5) . . ? N1 N2 C4 121.79(14) . . ? N1 C1 C2 109.95(15) . . ? N1 C1 C21 121.64(15) . . ? N2 N1 Re1 118.90(11) . . ? N2 C3 C2 107.62(16) . . ? N2 C3 H3 126.2 . . ? N3 Re1 N5 83.30(5) . . ? N3 N4 C14 126.16(14) . . ? N3 C11 C12 110.30(15) . . ? N3 C11 C24 124.33(15) . . ? N4 N3 Re1 125.11(11) . . ? N4 C13 C12 108.02(15) . . ? N4 C13 H13 126.0 . . ? N5 C27 H27C 109.5 . . ? N5 C27 H27B 109.5 . . ? N5 C27 H27A 109.5 . . ? C1 N1 Re1 133.47(12) . . ? C1 N1 N2 106.05(14) . . ? C1 C2 H2 127.1 . . ? C1 C21 H21 108.0 . . ? C1 C21 C22 109.56(15) . . ? C1 C21 C23 112.19(15) . . ? C2 C1 C21 128.33(16) . . ? C2 C3 H3 126.2 . . ? C3 N2 N1 110.59(15) . . ? C3 N2 C4 127.56(15) . . ? C3 C2 C1 105.76(16) . . ? C3 C2 H2 127.1 . . ? C4 C5 H5 119.6 . . ? C4 C5 C6 120.81(18) . . ? C4 C9 N5 117.89(15) . . ? C5 C4 N2 118.56(16) . . ? C5 C4 C9 120.94(17) . . ? C5 C6 C10 120.46(18) . . ? C6 C5 H5 119.6 . . ? C6 C7 H7 119.0 . . ? C6 C7 C8 121.98(18) . . ? C6 C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? C6 C10 H10A 109.5 . . ? C7 C6 C5 117.83(17) . . ? C7 C6 C10 121.69(18) . . ? C7 C8 H8 120.0 . . ? C8 C7 H7 119.0 . . ? C8 C9 N5 123.61(16) . . ? C8 C9 C4 118.50(16) . . ? C9 N5 Re1 100.59(10) . . ? C9 N5 C19 108.02(13) . . ? C9 N5 C27 112.94(14) . . ? C9 C4 N2 120.49(15) . . ? C9 C8 C7 119.93(18) . . ? C9 C8 H8 120.0 . . ? H10B C10 H10C 109.5 . . ? H10B C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? C11 N3 Re1 128.89(11) . . ? C11 N3 N4 105.95(13) . . ? C11 C12 H12 127.1 . . ? C11 C24 H24 108.5 . . ? C11 C24 C25 110.64(16) . . ? C11 C24 C26 110.21(16) . . ? C12 C11 C24 125.28(16) . . ? C12 C13 H13 126.0 . . ? C13 N4 N3 109.82(14) . . ? C13 N4 C14 124.01(14) . . ? C13 C12 C11 105.90(16) . . ? C13 C12 H12 127.1 . . ? C14 C15 H15 118.9 . . ? C14 C19 N5 123.66(15) . . ? C15 C14 N4 115.94(15) . . ? C15 C14 C19 118.69(16) . . ? C15 C16 C20 120.44(17) . . ? C16 C15 C14 122.26(17) . . ? C16 C15 H15 118.9 . . ? C16 C17 H17 119.8 . . ? C16 C20 H20C 109.5 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? C17 C16 C15 118.05(16) . . ? C17 C16 C20 121.51(16) . . ? C17 C18 H18 119.3 . . ? C17 C18 C19 121.49(17) . . ? C18 C17 C16 120.31(17) . . ? C18 C17 H17 119.8 . . ? C18 C19 N5 117.63(15) . . ? C18 C19 C14 118.71(16) . . ? C19 N5 Re1 117.44(11) . . ? C19 N5 C27 107.37(13) . . ? C19 C14 N4 125.28(15) . . ? C19 C18 H18 119.3 . . ? H20C C20 H20A 109.5 . . ? H20C C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C21 C22 H22C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? C21 C23 H23A 109.5 . . ? C22 C21 H21 108.0 . . ? C22 C21 C23 110.92(17) . . ? H22C C22 H22A 109.5 . . ? H22C C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C21 H21 108.0 . . ? H23B C23 H23C 109.5 . . ? H23B C23 H23A 109.5 . . ? H23C C23 H23A 109.5 . . ? C24 C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? C24 C25 H25A 109.5 . . ? C24 C26 H26C 109.5 . . ? C24 C26 H26B 109.5 . . ? C24 C26 H26A 109.5 . . ? C25 C24 H24 108.5 . . ? C25 C24 C26 110.31(16) . . ? H25B C25 H25C 109.5 . . ? H25B C25 H25A 109.5 . . ? H25C C25 H25A 109.5 . . ? C26 C24 H24 108.5 . . ? H26C C26 H26B 109.5 . . ? H26C C26 H26A 109.5 . . ? H26B C26 H26A 109.5 . . ? C27 N5 Re1 110.51(10) . . ? H27C C27 H27B 109.5 . . ? H27C C27 H27A 109.5 . . ? H27B C27 H27A 109.5 . . ? C28 Re1 N1 172.10(6) . . ? C28 Re1 N3 88.00(6) . . ? C28 Re1 N5 96.23(7) . . ? C29 Re1 N1 96.10(7) . . ? C29 Re1 N3 97.48(7) . . ? C29 Re1 N5 174.24(7) . . ? C29 Re1 C28 89.51(8) . . ? C29 Re1 C30 83.61(7) . . ? C30 Re1 N1 95.56(6) . . ? C30 Re1 N3 178.20(7) . . ? C30 Re1 N5 95.76(6) . . ? C30 Re1 C28 90.58(7) . . ? Cl1 C1S Cl2 111.27(11) . . ? Cl1 C1S H1SB 109.4 . . ? Cl1 C1S H1SA 109.4 . . ? Cl2 C1S H1SB 109.4 . . ? Cl2 C1S H1SA 109.4 . . ? H1SB C1S H1SA 108.0 . . ? Cl3 C2S H2SB 109.2 . . ? Cl3 C2S H2SA 109.2 . . ? Cl4 C2S Cl3 112.23(13) . . ? Cl4 C2S H2SB 109.2 . . ? Cl4 C2S H2SA 109.2 . . ? H2SB C2S H2SA 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Re1 N1 N2 C3 165.79(11) . . . . ? Re1 N1 N2 C4 -11.6(2) . . . . ? Re1 N1 C1 C2 -163.68(12) . . . . ? Re1 N1 C1 C21 19.4(2) . . . . ? Re1 N3 N4 C13 -177.97(13) . . . . ? Re1 N3 N4 C14 1.5(2) . . . . ? Re1 N3 C11 C12 177.25(13) . . . . ? Re1 N3 C11 C24 0.6(3) . . . . ? Re1 N5 C9 C4 -62.68(15) . . . . ? Re1 N5 C9 C8 117.50(15) . . . . ? Re1 N5 C19 C14 -30.0(2) . . . . ? Re1 N5 C19 C18 149.38(14) . . . . ? N1 Re1 N3 N4 49.44(14) . . . . ? N1 Re1 N3 C11 -127.58(16) . . . . ? N1 Re1 N5 C9 70.78(10) . . . . ? N1 Re1 N5 C19 -46.08(11) . . . . ? N1 Re1 N5 C27 -169.67(11) . . . . ? N1 Re1 C28 O1 -29(3) . . . . ? N1 Re1 C29 O2 -86(4) . . . . ? N1 Re1 C30 O3 101(3) . . . . ? N1 N2 C3 C2 1.6(2) . . . . ? N1 N2 C4 C5 -131.18(17) . . . . ? N1 N2 C4 C9 50.1(2) . . . . ? N1 C1 C2 C3 -0.3(2) . . . . ? N1 C1 C21 C22 91.6(2) . . . . ? N1 C1 C21 C23 -144.75(18) . . . . ? N2 N1 C1 C2 1.27(19) . . . . ? N2 N1 C1 C21 -175.69(15) . . . . ? N2 C4 C5 C6 -177.84(16) . . . . ? N2 C4 C9 N5 -1.9(2) . . . . ? N2 C4 C9 C8 177.94(15) . . . . ? N3 Re1 N1 N2 -122.96(12) . . . . ? N3 Re1 N1 C1 40.47(16) . . . . ? N3 Re1 N5 C9 157.82(11) . . . . ? N3 Re1 N5 C19 40.96(12) . . . . ? N3 Re1 N5 C27 -82.63(11) . . . . ? N3 Re1 C28 O1 9(2) . . . . ? N3 Re1 C29 O2 -173(4) . . . . ? N3 Re1 C30 O3 -122(3) . . . . ? N3 N4 C13 C12 0.8(2) . . . . ? N3 N4 C14 C15 -153.19(17) . . . . ? N3 N4 C14 C19 30.2(3) . . . . ? N3 C11 C12 C13 0.7(2) . . . . ? N3 C11 C24 C25 -127.59(19) . . . . ? N3 C11 C24 C26 110.1(2) . . . . ? N4 N3 C11 C12 -0.2(2) . . . . ? N4 N3 C11 C24 -176.89(17) . . . . ? N4 C14 C15 C16 -171.93(16) . . . . ? N4 C14 C19 N5 -11.9(3) . . . . ? N4 C14 C19 C18 168.70(17) . . . . ? N5 Re1 N1 N2 -38.94(11) . . . . ? N5 Re1 N1 C1 124.50(16) . . . . ? N5 Re1 N3 N4 -29.21(14) . . . . ? N5 Re1 N3 C11 153.77(16) . . . . ? N5 Re1 C28 O1 -74(2) . . . . ? N5 Re1 C29 O2 -75(4) . . . . ? N5 Re1 C30 O3 180(100) . . . . ? C1 N1 N2 C3 -1.78(19) . . . . ? C1 N1 N2 C4 -179.22(15) . . . . ? C1 C2 C3 N2 -0.8(2) . . . . ? C2 C1 C21 C22 -84.8(2) . . . . ? C2 C1 C21 C23 38.9(3) . . . . ? C3 N2 C4 C5 51.9(2) . . . . ? C3 N2 C4 C9 -126.91(19) . . . . ? C4 N2 C3 C2 178.85(17) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C4 C5 C6 C10 178.40(18) . . . . ? C5 C4 C9 N5 179.37(15) . . . . ? C5 C4 C9 C8 -0.8(2) . . . . ? C5 C6 C7 C8 -0.7(3) . . . . ? C6 C7 C8 C9 0.8(3) . . . . ? C7 C8 C9 N5 179.78(15) . . . . ? C7 C8 C9 C4 0.0(2) . . . . ? C9 N5 C19 C14 -142.78(17) . . . . ? C9 N5 C19 C18 36.6(2) . . . . ? C9 C4 C5 C6 0.9(3) . . . . ? C10 C6 C7 C8 -179.23(18) . . . . ? C11 N3 N4 C13 -0.4(2) . . . . ? C11 N3 N4 C14 179.09(17) . . . . ? C11 C12 C13 N4 -0.9(2) . . . . ? C12 C11 C24 C25 56.2(3) . . . . ? C12 C11 C24 C26 -66.1(2) . . . . ? C13 N4 C14 C15 26.2(3) . . . . ? C13 N4 C14 C19 -150.36(19) . . . . ? C14 N4 C13 C12 -178.65(17) . . . . ? C14 C15 C16 C17 1.4(3) . . . . ? C14 C15 C16 C20 -177.76(18) . . . . ? C15 C14 C19 N5 171.61(16) . . . . ? C15 C14 C19 C18 -7.8(3) . . . . ? C15 C16 C17 C18 -4.6(3) . . . . ? C16 C17 C18 C19 1.6(3) . . . . ? C17 C18 C19 N5 -174.71(17) . . . . ? C17 C18 C19 C14 4.7(3) . . . . ? C19 N5 C9 C4 60.95(19) . . . . ? C19 N5 C9 C8 -118.87(17) . . . . ? C19 C14 C15 C16 4.9(3) . . . . ? C20 C16 C17 C18 174.51(19) . . . . ? C21 C1 C2 C3 176.36(17) . . . . ? C24 C11 C12 C13 177.36(19) . . . . ? C27 N5 C9 C4 179.53(15) . . . . ? C27 N5 C9 C8 -0.3(2) . . . . ? C27 N5 C19 C14 95.1(2) . . . . ? C27 N5 C19 C18 -85.45(19) . . . . ? C28 Re1 N1 N2 -85.1(5) . . . . ? C28 Re1 N1 C1 78.4(5) . . . . ? C28 Re1 N3 N4 -125.72(15) . . . . ? C28 Re1 N3 C11 57.26(16) . . . . ? C28 Re1 N5 C9 -114.94(11) . . . . ? C28 Re1 N5 C19 128.21(12) . . . . ? C28 Re1 N5 C27 4.61(12) . . . . ? C28 Re1 C29 O2 99(4) . . . . ? C28 Re1 C30 O3 -84(3) . . . . ? C29 Re1 N1 N2 139.95(12) . . . . ? C29 Re1 N1 C1 -56.62(16) . . . . ? C29 Re1 N3 N4 145.04(14) . . . . ? C29 Re1 N3 C11 -31.98(17) . . . . ? C29 Re1 N5 C9 59.7(6) . . . . ? C29 Re1 N5 C19 -57.2(6) . . . . ? C29 Re1 N5 C27 179(6) . . . . ? C29 Re1 C28 O1 106(2) . . . . ? C29 Re1 C30 O3 6(3) . . . . ? C30 Re1 N1 N2 55.81(13) . . . . ? C30 Re1 N1 C1 -140.76(16) . . . . ? C30 Re1 N3 N4 -88(2) . . . . ? C30 Re1 N3 C11 95(2) . . . . ? C30 Re1 N5 C9 -23.72(11) . . . . ? C30 Re1 N5 C19 -140.57(12) . . . . ? C30 Re1 N5 C27 95.83(12) . . . . ? C30 Re1 C28 O1 -170(2) . . . . ? C30 Re1 C29 O2 9(4) . . . . ?