# Copyright The Royal Society of Chemistry, 1998 # Title: Synthesis and Reactions of the Rhenium Fulvene Complexes # (eta-6-C5Me4CH2)Re(CO)2(C6F4R) (R = F and CF3): # Products Derived from Initial C-F Activation data_5b #for the structure of trans-Re(eta-5-C5(CH3)4CH2Br)(CO)2(C6F5)Br _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Br2 F5 O2 Re' _chemical_formula_weight 703.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Re' 'Re' -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 '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 8.3721(11) _cell_length_b 9.2456(13) _cell_length_c 14.570(2) _cell_angle_alpha 79.561(12) _cell_angle_beta 75.292(11) _cell_angle_gamma 63.331(10) _cell_volume 971.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 25.05 _exptl_crystal_description Prismatic _exptl_crystal_colour Orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not _measured' _exptl_crystal_density_diffrn 2.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 10.421 _exptl_absorpt_correction_type 'Semiempirical (Psi-scan)' _exptl_absorpt_correction_T_min '0.03' _exptl_absorpt_correction_T_max '0.28' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens R3m' _diffrn_measurement_method \q/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_reflns_number 3627 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3343 _reflns_number_gt 2952 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/P4-PC version V4.27 (1991)' _computing_cell_refinement 'Siemens P3/P4-PC version V4.27 (1991)' _computing_data_reduction 'XDISK in SHELXTL/PC (Sheldrick,1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL/PC (Sheldrick,1991)' _computing_publication_material ; CIFTAB (Sheldrick,1997). ; _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 w=1/[\s^2^(Fo^2^)+(0.08P)^2^+23.44P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3343 _refine_ls_number_parameters 253 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1310 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.923 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re Re 0.98419(5) 0.20483(5) 0.25212(3) 0.02229(16) Uani 1 d . . . Br1 Br 1.28344(17) 0.08797(17) 0.32069(10) 0.0457(3) Uani 1 d . . . Br2 Br 0.4215(2) 0.2831(2) 0.51514(11) 0.0584(4) Uani 1 d . . . F1 F 0.7746(12) -0.0178(10) 0.2279(5) 0.049(2) Uani 1 d . . . F2 F 0.6380(12) -0.0419(10) 0.0894(6) 0.054(2) Uani 1 d . . . F3 F 0.6367(12) 0.1501(12) -0.0753(6) 0.060(2) Uani 1 d . . . F4 F 0.7864(14) 0.3646(12) -0.0992(5) 0.065(3) Uani 1 d . . . F5 F 0.9366(12) 0.3852(10) 0.0321(5) 0.051(2) Uani 1 d . . . O1 O 1.2735(13) 0.2586(14) 0.0893(8) 0.062(3) Uani 1 d . . . O2 O 1.1314(16) -0.1707(12) 0.2752(7) 0.057(3) Uani 1 d . . . C1 C 0.7202(14) 0.2772(13) 0.3699(7) 0.027(2) Uani 1 d . . . C2 C 0.6740(16) 0.3855(14) 0.2897(7) 0.030(2) Uani 1 d . . . C3 C 0.7841(18) 0.4780(16) 0.2668(8) 0.038(3) Uani 1 d . . . C4 C 0.8951(17) 0.4212(14) 0.3337(9) 0.036(3) Uani 1 d . . . C5 C 0.8524(15) 0.3015(14) 0.4003(8) 0.030(2) Uani 1 d . . . C6 C 0.6357(16) 0.1656(14) 0.4197(9) 0.036(3) Uani 1 d . . . H6C H 0.7231 0.0722 0.4505 0.043 Uiso 1 calc R . . H6D H 0.5994 0.1274 0.3742 0.043 Uiso 1 calc R . . C7 C 0.5218(14) 0.4110(15) 0.2431(10) 0.039(3) Uani 1 d . . . H7D H 0.5155 0.4901 0.1898 0.059 Uiso 1 calc R . . H7E H 0.4086 0.4488 0.2882 0.059 Uiso 1 calc R . . H7F H 0.5440 0.3103 0.2215 0.059 Uiso 1 calc R . . C8 C 0.752(2) 0.6172(15) 0.1950(11) 0.050(3) Uani 1 d . . . H8D H 0.6670 0.6229 0.1597 0.074 Uiso 1 calc R . . H8E H 0.8654 0.6040 0.1524 0.074 Uiso 1 calc R . . H8F H 0.7040 0.7155 0.2262 0.074 Uiso 1 calc R . . C9 C 1.0167(17) 0.4956(16) 0.3416(11) 0.043(3) Uani 1 d . . . H9D H 1.0814 0.4379 0.3921 0.065 Uiso 1 calc R . . H9E H 0.9444 0.6073 0.3549 0.065 Uiso 1 calc R . . H9F H 1.1023 0.4895 0.2827 0.065 Uiso 1 calc R . . C10 C 0.9146(19) 0.2352(17) 0.4934(8) 0.044(3) Uani 1 d . . . H10D H 1.0059 0.2687 0.4969 0.065 Uiso 1 calc R . . H10E H 0.9648 0.1188 0.4978 0.065 Uiso 1 calc R . . H10F H 0.8126 0.2758 0.5449 0.065 Uiso 1 calc R . . C11 C 0.8717(15) 0.1800(12) 0.1376(7) 0.024(2) Uani 1 d . . . C12 C 0.7905(16) 0.0755(13) 0.1457(7) 0.028(2) Uani 1 d . . . C13 C 0.7128(16) 0.0631(14) 0.0772(8) 0.031(2) Uani 1 d . . . C14 C 0.7125(16) 0.1608(15) -0.0066(8) 0.033(3) Uani 1 d . . . C15 C 0.7903(19) 0.2676(16) -0.0193(8) 0.039(3) Uani 1 d . . . C16 C 0.8663(16) 0.2748(14) 0.0520(8) 0.032(2) Uani 1 d . . . C17 C 1.1671(15) 0.2387(15) 0.1462(9) 0.035(3) Uani 1 d . . . C18 C 1.0822(14) -0.0410(12) 0.2608(7) 0.024(2) Uani 1 d U . . 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 Re 0.0219(2) 0.0250(2) 0.0241(2) -0.00126(15) -0.00409(16) -0.01395(18) Br1 0.0299(6) 0.0530(8) 0.0578(8) -0.0073(6) -0.0184(6) -0.0144(6) Br2 0.0419(8) 0.0706(10) 0.0504(8) -0.0048(7) 0.0123(6) -0.0242(7) F1 0.094(6) 0.058(5) 0.037(4) 0.010(3) -0.026(4) -0.066(5) F2 0.073(6) 0.056(5) 0.066(5) 0.002(4) -0.030(4) -0.049(4) F3 0.070(6) 0.096(7) 0.039(4) -0.010(4) -0.020(4) -0.051(5) F4 0.094(7) 0.093(7) 0.035(4) 0.025(4) -0.031(4) -0.065(6) F5 0.075(6) 0.062(5) 0.041(4) 0.018(4) -0.022(4) -0.052(5) O1 0.037(5) 0.078(8) 0.062(6) 0.006(5) 0.011(5) -0.030(5) O2 0.085(8) 0.041(5) 0.054(6) 0.020(4) -0.030(6) -0.034(5) C1 0.025(5) 0.029(5) 0.025(5) -0.008(4) 0.004(4) -0.013(5) C2 0.037(6) 0.041(6) 0.021(5) -0.003(5) -0.010(5) -0.022(5) C3 0.056(8) 0.051(7) 0.031(6) -0.001(5) -0.002(5) -0.048(7) C4 0.039(7) 0.027(6) 0.050(7) -0.003(5) -0.008(6) -0.022(5) C5 0.026(6) 0.035(6) 0.028(6) -0.004(5) -0.004(4) -0.012(5) C6 0.030(6) 0.030(6) 0.047(7) -0.006(5) 0.005(5) -0.018(5) C7 0.011(5) 0.039(7) 0.061(8) -0.028(6) -0.002(5) 0.001(5) C8 0.054(8) 0.030(6) 0.065(9) -0.013(6) 0.000(7) -0.020(6) C9 0.034(7) 0.041(7) 0.065(9) -0.009(6) -0.004(6) -0.026(6) C10 0.048(8) 0.049(8) 0.030(6) -0.004(5) -0.011(6) -0.015(6) C11 0.032(6) 0.025(5) 0.021(5) -0.002(4) -0.008(4) -0.015(5) C12 0.039(6) 0.026(5) 0.025(5) -0.004(4) -0.004(5) -0.019(5) C13 0.033(6) 0.031(6) 0.037(6) -0.006(5) -0.010(5) -0.018(5) C14 0.034(6) 0.050(7) 0.030(6) -0.011(5) -0.006(5) -0.027(6) C15 0.052(8) 0.052(7) 0.025(6) 0.002(5) -0.008(5) -0.034(6) C16 0.034(6) 0.039(6) 0.033(6) -0.002(5) -0.007(5) -0.024(5) C17 0.024(6) 0.040(7) 0.043(7) 0.000(5) -0.003(5) -0.018(5) C18 0.022(3) 0.022(3) 0.024(3) 0.002(2) -0.007(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re C17 1.970(12) . Y Re C18 2.032(10) . Y Re C11 2.203(10) . Y Re C4 2.246(12) . Y Re C5 2.298(11) . Y Re C1 2.332(10) . Y Re C3 2.334(14) . Y Re C2 2.356(12) . Y Re Br1 2.6254(13) . Y Br2 C6 1.965(11) . Y F1 C12 1.358(12) . N F2 C13 1.339(13) . N F3 C14 1.352(13) . N F4 C15 1.333(14) . N F5 C16 1.348(13) . N O1 C17 1.110(15) . N O2 C18 1.077(13) . N C1 C2 1.406(15) . N C1 C5 1.407(16) . N C1 C6 1.488(15) . N C2 C3 1.462(15) . N C2 C7 1.501(15) . N C3 C4 1.388(18) . N C3 C8 1.473(18) . N C4 C5 1.444(16) . N C4 C9 1.496(16) . N C5 C10 1.502(16) . N C11 C12 1.384(15) . N C11 C16 1.387(15) . N C12 C13 1.368(16) . N C13 C14 1.381(17) . N C14 C15 1.372(17) . N C15 C16 1.373(16) . N 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 C17 Re C18 100.5(5) . . Y C17 Re C11 83.9(5) . . Y C18 Re C11 80.8(4) . . Y C17 Re C4 100.6(5) . . N C18 Re C4 144.8(4) . . N C11 Re C4 129.3(4) . . N C17 Re C5 133.9(5) . . N C18 Re C5 110.8(4) . . N C11 Re C5 132.8(4) . . N C4 Re C5 37.0(4) . . N C17 Re C1 157.1(5) . . N C18 Re C1 102.4(4) . . N C11 Re C1 98.3(4) . . N C4 Re C1 60.3(4) . . N C5 Re C1 35.4(4) . . N C17 Re C3 97.0(4) . . N C18 Re C3 161.1(4) . . N C11 Re C3 94.1(4) . . N C4 Re C3 35.2(4) . . N C5 Re C3 59.9(4) . . N C1 Re C3 60.1(4) . . N C17 Re C2 125.9(4) . . N C18 Re C2 125.1(4) . . N C11 Re C2 77.2(4) . . N C4 Re C2 59.2(4) . . N C5 Re C2 58.4(4) . . N C1 Re C2 34.9(4) . . N C3 Re C2 36.3(4) . . N C17 Re Br1 75.1(4) . . Y C18 Re Br1 73.2(3) . . Y C11 Re Br1 142.6(3) . . Y C4 Re Br1 85.5(3) . . N C5 Re Br1 82.4(3) . . N C1 Re Br1 113.1(3) . . N C3 Re Br1 118.6(3) . . N C2 Re Br1 140.0(2) . . N C2 C1 C5 107.7(10) . . N C2 C1 C6 127.0(11) . . N C5 C1 C6 125.2(11) . . N C2 C1 Re 73.5(6) . . N C5 C1 Re 71.0(6) . . N C6 C1 Re 124.8(7) . . N C1 C2 C3 109.1(10) . . N C1 C2 C7 124.0(11) . . N C3 C2 C7 126.6(11) . . N C1 C2 Re 71.6(6) . . N C3 C2 Re 71.0(7) . . N C7 C2 Re 128.2(7) . . N C4 C3 C2 105.9(10) . . N C4 C3 C8 130.5(11) . . N C2 C3 C8 123.0(12) . . N C4 C3 Re 68.9(7) . . N C2 C3 Re 72.7(7) . . N C8 C3 Re 129.9(9) . . N C3 C4 C5 109.5(10) . . N C3 C4 C9 123.1(11) . . N C5 C4 C9 126.7(12) . . N C3 C4 Re 75.8(7) . . N C5 C4 Re 73.4(6) . . N C9 C4 Re 124.7(9) . . N C1 C5 C4 107.7(10) . . N C1 C5 C10 125.7(11) . . N C4 C5 C10 125.9(11) . . N C1 C5 Re 73.7(6) . . N C4 C5 Re 69.5(6) . . N C10 C5 Re 129.7(8) . . N C1 C6 Br2 108.9(8) . . Y C12 C11 C16 113.3(9) . . N C12 C11 Re 123.6(8) . . N C16 C11 Re 123.0(8) . . N F1 C12 C13 115.0(9) . . N F1 C12 C11 120.3(9) . . N C13 C12 C11 124.7(10) . . N F2 C13 C12 121.5(10) . . N F2 C13 C14 119.4(10) . . N C12 C13 C14 119.1(10) . . N F3 C14 C15 120.7(11) . . N F3 C14 C13 120.0(10) . . N C15 C14 C13 119.3(10) . . N F4 C15 C14 119.4(11) . . N F4 C15 C16 121.5(11) . . N C14 C15 C16 119.1(11) . . N F5 C16 C15 113.8(10) . . N F5 C16 C11 121.6(10) . . N C15 C16 C11 124.6(11) . . N O1 C17 Re 177.0(12) . . N O2 C18 Re 172.6(10) . . N 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 C17 Re C1 C2 40.7(14) . . . . N C18 Re C1 C2 -135.5(6) . . . . N C11 Re C1 C2 -53.1(7) . . . . N C4 Re C1 C2 77.6(7) . . . . N C5 Re C1 C2 115.9(9) . . . . N C3 Re C1 C2 36.9(6) . . . . N Br1 Re C1 C2 147.6(5) . . . . N C17 Re C1 C5 -75.2(13) . . . . N C18 Re C1 C5 108.6(7) . . . . N C11 Re C1 C5 -169.1(7) . . . . N C4 Re C1 C5 -38.3(7) . . . . N C3 Re C1 C5 -79.1(7) . . . . N C2 Re C1 C5 -115.9(9) . . . . N Br1 Re C1 C5 31.7(7) . . . . N C17 Re C1 C6 164.6(11) . . . . N C18 Re C1 C6 -11.5(11) . . . . N C11 Re C1 C6 70.8(10) . . . . N C4 Re C1 C6 -158.4(11) . . . . N C5 Re C1 C6 -120.1(13) . . . . N C3 Re C1 C6 160.8(11) . . . . N C2 Re C1 C6 123.9(13) . . . . N Br1 Re C1 C6 -88.4(10) . . . . N C5 C1 C2 C3 1.7(13) . . . . N C6 C1 C2 C3 177.1(11) . . . . N Re C1 C2 C3 -61.4(9) . . . . N C5 C1 C2 C7 -172.6(10) . . . . N C6 C1 C2 C7 2.8(18) . . . . N Re C1 C2 C7 124.3(11) . . . . N C5 C1 C2 Re 63.2(7) . . . . N C6 C1 C2 Re -121.5(11) . . . . N C17 Re C2 C1 -161.7(7) . . . . N C18 Re C2 C1 56.8(8) . . . . N C11 Re C2 C1 125.7(7) . . . . N C4 Re C2 C1 -81.3(7) . . . . N C5 Re C2 C1 -37.7(6) . . . . N C3 Re C2 C1 -118.6(9) . . . . N Br1 Re C2 C1 -50.0(8) . . . . N C17 Re C2 C3 -43.1(8) . . . . N C18 Re C2 C3 175.5(6) . . . . N C11 Re C2 C3 -115.7(7) . . . . N C4 Re C2 C3 37.4(7) . . . . N C5 Re C2 C3 81.0(7) . . . . N C1 Re C2 C3 118.6(9) . . . . N Br1 Re C2 C3 68.6(7) . . . . N C17 Re C2 C7 79.0(12) . . . . N C18 Re C2 C7 -62.4(12) . . . . N C11 Re C2 C7 6.5(10) . . . . N C4 Re C2 C7 159.5(12) . . . . N C5 Re C2 C7 -156.9(12) . . . . N C1 Re C2 C7 -119.3(13) . . . . N C3 Re C2 C7 122.1(13) . . . . N Br1 Re C2 C7 -169.3(8) . . . . N C1 C2 C3 C4 0.5(14) . . . . N C7 C2 C3 C4 174.7(11) . . . . N Re C2 C3 C4 -61.3(9) . . . . N C1 C2 C3 C8 -171.4(11) . . . . N C7 C2 C3 C8 3(2) . . . . N Re C2 C3 C8 126.8(12) . . . . N C1 C2 C3 Re 61.8(8) . . . . N C7 C2 C3 Re -124.0(11) . . . . N C17 Re C3 C4 -98.6(8) . . . . N C18 Re C3 C4 103.7(13) . . . . N C11 Re C3 C4 177.1(7) . . . . N C5 Re C3 C4 38.8(7) . . . . N C1 Re C3 C4 79.9(7) . . . . N C2 Re C3 C4 115.3(10) . . . . N Br1 Re C3 C4 -21.8(8) . . . . N C17 Re C3 C2 146.1(7) . . . . N C18 Re C3 C2 -11.6(16) . . . . N C11 Re C3 C2 61.8(6) . . . . N C4 Re C3 C2 -115.3(10) . . . . N C5 Re C3 C2 -76.5(7) . . . . N C1 Re C3 C2 -35.4(6) . . . . N Br1 Re C3 C2 -137.1(5) . . . . N C17 Re C3 C8 27.2(12) . . . . N C18 Re C3 C8 -130.5(13) . . . . N C11 Re C3 C8 -57.1(12) . . . . N C4 Re C3 C8 125.8(14) . . . . N C5 Re C3 C8 164.7(13) . . . . N C1 Re C3 C8 -154.3(13) . . . . N C2 Re C3 C8 -118.9(14) . . . . N Br1 Re C3 C8 104.0(11) . . . . N C2 C3 C4 C5 -2.6(14) . . . . N C8 C3 C4 C5 168.5(13) . . . . N Re C3 C4 C5 -66.3(8) . . . . N C2 C3 C4 C9 -173.8(11) . . . . N C8 C3 C4 C9 -3(2) . . . . N Re C3 C4 C9 122.4(12) . . . . N C2 C3 C4 Re 63.8(9) . . . . N C8 C3 C4 Re -125.1(14) . . . . N C17 Re C4 C3 87.1(7) . . . . N C18 Re C4 C3 -147.0(7) . . . . N C11 Re C4 C3 -3.7(9) . . . . N C5 Re C4 C3 -115.7(10) . . . . N C1 Re C4 C3 -79.2(7) . . . . N C2 Re C4 C3 -38.6(6) . . . . N Br1 Re C4 C3 160.9(7) . . . . N C17 Re C4 C5 -157.2(7) . . . . N C18 Re C4 C5 -31.3(11) . . . . N C11 Re C4 C5 112.0(7) . . . . N C1 Re C4 C5 36.6(6) . . . . N C3 Re C4 C5 115.7(10) . . . . N C2 Re C4 C5 77.1(7) . . . . N Br1 Re C4 C5 -83.3(6) . . . . N C17 Re C4 C9 -33.6(12) . . . . N C18 Re C4 C9 92.3(12) . . . . N C11 Re C4 C9 -124.4(10) . . . . N C5 Re C4 C9 123.6(14) . . . . N C1 Re C4 C9 160.1(12) . . . . N C3 Re C4 C9 -120.7(14) . . . . N C2 Re C4 C9 -159.3(13) . . . . N Br1 Re C4 C9 40.2(11) . . . . N C2 C1 C5 C4 -3.2(12) . . . . N C6 C1 C5 C4 -178.7(10) . . . . N Re C1 C5 C4 61.6(8) . . . . N C2 C1 C5 C10 167.7(11) . . . . N C6 C1 C5 C10 -7.8(18) . . . . N Re C1 C5 C10 -127.5(12) . . . . N C2 C1 C5 Re -64.8(8) . . . . N C6 C1 C5 Re 119.7(10) . . . . N C3 C4 C5 C1 3.7(14) . . . . N C9 C4 C5 C1 174.5(12) . . . . N Re C4 C5 C1 -64.2(8) . . . . N C3 C4 C5 C10 -167.2(11) . . . . N C9 C4 C5 C10 4(2) . . . . N Re C4 C5 C10 124.9(11) . . . . N C3 C4 C5 Re 67.9(9) . . . . N C9 C4 C5 Re -121.3(13) . . . . N C17 Re C5 C1 148.5(7) . . . . N C18 Re C5 C1 -82.1(7) . . . . N C11 Re C5 C1 14.8(9) . . . . N C4 Re C5 C1 116.6(10) . . . . N C3 Re C5 C1 79.7(7) . . . . N C2 Re C5 C1 37.1(6) . . . . N Br1 Re C5 C1 -150.8(6) . . . . N C17 Re C5 C4 31.9(9) . . . . N C18 Re C5 C4 161.3(7) . . . . N C11 Re C5 C4 -101.8(8) . . . . N C1 Re C5 C4 -116.6(10) . . . . N C3 Re C5 C4 -36.9(7) . . . . N C2 Re C5 C4 -79.5(7) . . . . N Br1 Re C5 C4 92.6(6) . . . . N C17 Re C5 C10 -88.4(13) . . . . N C18 Re C5 C10 41.1(12) . . . . N C11 Re C5 C10 137.9(10) . . . . N C4 Re C5 C10 -120.3(14) . . . . N C1 Re C5 C10 123.1(14) . . . . N C3 Re C5 C10 -157.2(13) . . . . N C2 Re C5 C10 160.3(13) . . . . N Br1 Re C5 C10 -27.7(11) . . . . N C2 C1 C6 Br2 -86.8(12) . . . . N C5 C1 C6 Br2 87.8(12) . . . . N Re C1 C6 Br2 178.1(5) . . . . N C17 Re C11 C12 145.3(10) . . . . N C18 Re C11 C12 43.7(9) . . . . N C4 Re C11 C12 -115.9(9) . . . . N C5 Re C11 C12 -66.3(11) . . . . N C1 Re C11 C12 -57.7(10) . . . . N C3 Re C11 C12 -118.1(9) . . . . N C2 Re C11 C12 -85.7(9) . . . . N Br1 Re C11 C12 89.8(10) . . . . N C17 Re C11 C16 -38.4(10) . . . . N C18 Re C11 C16 -140.1(10) . . . . N C4 Re C11 C16 60.3(11) . . . . N C5 Re C11 C16 109.9(10) . . . . N C1 Re C11 C16 118.5(9) . . . . N C3 Re C11 C16 58.2(10) . . . . N C2 Re C11 C16 90.5(10) . . . . N Br1 Re C11 C16 -94.0(10) . . . . N C16 C11 C12 F1 -175.8(10) . . . . N Re C11 C12 F1 0.8(15) . . . . N C16 C11 C12 C13 0.5(16) . . . . N Re C11 C12 C13 177.0(9) . . . . N F1 C12 C13 F2 -4.2(16) . . . . N C11 C12 C13 F2 179.4(11) . . . . N F1 C12 C13 C14 176.1(10) . . . . N C11 C12 C13 C14 -0.3(18) . . . . N F2 C13 C14 F3 0.2(17) . . . . N C12 C13 C14 F3 179.9(11) . . . . N F2 C13 C14 C15 -179.6(11) . . . . N C12 C13 C14 C15 0.1(18) . . . . N F3 C14 C15 F4 1.8(19) . . . . N C13 C14 C15 F4 -178.5(11) . . . . N F3 C14 C15 C16 -179.8(11) . . . . N C13 C14 C15 C16 -0.1(19) . . . . N F4 C15 C16 F5 -0.9(18) . . . . N C14 C15 C16 F5 -179.3(11) . . . . N F4 C15 C16 C11 178.6(12) . . . . N C14 C15 C16 C11 0(2) . . . . N C12 C11 C16 F5 179.1(11) . . . . N Re C11 C16 F5 2.5(16) . . . . N C12 C11 C16 C15 -0.5(17) . . . . N Re C11 C16 C15 -177.0(10) . . . . N C18 Re C17 O1 -102(22) . . . . N C11 Re C17 O1 179(100) . . . . N C4 Re C17 O1 50(22) . . . . N C5 Re C17 O1 31(23) . . . . N C1 Re C17 O1 82(22) . . . . N C3 Re C17 O1 85(22) . . . . N C2 Re C17 O1 109(22) . . . . N Br1 Re C17 O1 -32(22) . . . . N C17 Re C18 O2 134(8) . . . . N C11 Re C18 O2 -144(8) . . . . N C4 Re C18 O2 8(8) . . . . N C5 Re C18 O2 -12(8) . . . . N C1 Re C18 O2 -48(8) . . . . N C3 Re C18 O2 -69(8) . . . . N C2 Re C18 O2 -77(8) . . . . N Br1 Re C18 O2 63(8) . . . . N _refine_diff_density_max 1.698 _refine_diff_density_min -1.818 _refine_diff_density_rms 0.274