# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1448 # Kinetic control of stereoselectivity of halide substitution in arene # ruthenium pyridyl oxazoline complexes; a rare case of net inversion. # # Adam J. Davenport, David L. Davies*, John Fawcett, Shaun A. Garatt and # David R. Russell. data_2a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 Br F6 N2 O Ru Sb' _chemical_formula_weight 727.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 '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' 'Ru' 'Ru' -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sb' 'Sb' -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.7030(7) _cell_length_b 12.0995(17) _cell_length_c 27.223(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2537.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 5.41 _cell_measurement_theta_max 12.58 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.904 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 3.293 _exptl_absorpt_correction_type 'psi scan' _exptl_absorpt_correction_T_min 0.41 _exptl_absorpt_correction_T_max 0.49 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 P4 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 1000 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 3234 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 1 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3152 _reflns_number_gt 2345 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+11.5775P] 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 0.0020(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(4) _refine_ls_number_reflns 3152 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1804 _refine_ls_wR_factor_gt 0.1566 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Sb1 Sb -0.73844(19) -0.60678(14) -0.15300(4) 0.0823(5) Uani 1 1 d . . . F1 F -0.940(2) -0.5745(18) -0.1871(5) 0.146(7) Uani 1 1 d . . . F2 F -0.629(2) -0.6236(14) -0.2119(5) 0.133(6) Uani 1 1 d . . . F3 F -0.541(2) -0.6422(17) -0.1194(5) 0.148(7) Uani 1 1 d . . . F4 F -0.846(3) -0.583(3) -0.0955(6) 0.263(16) Uani 1 1 d . . . F5 F -0.794(4) -0.7505(16) -0.1532(11) 0.222(12) Uani 1 1 d . . . F6 F -0.683(4) -0.4541(17) -0.1564(9) 0.220(11) Uani 1 1 d . . . Ru1 Ru -0.97907(14) -0.61711(9) -0.37240(4) 0.0429(3) Uani 1 1 d . . . Br1 Br -0.6914(2) -0.65081(19) -0.41400(8) 0.0800(7) Uani 1 1 d . . . O1 O -0.906(2) -0.3359(12) -0.4549(5) 0.095(5) Uani 1 1 d . . . N1 N -1.0043(16) -0.4959(9) -0.4270(4) 0.044(3) Uani 1 1 d . . . N2 N -0.8591(16) -0.4780(11) -0.3414(4) 0.053(3) Uani 1 1 d . . . C1 C -1.313(4) -0.500(2) -0.5353(9) 0.144(12) Uani 1 1 d . . . H1A H -1.4374 -0.4973 -0.5379 0.216 Uiso 1 1 calc R . . H1B H -1.2721 -0.5694 -0.5480 0.216 Uiso 1 1 calc R . . H1C H -1.2632 -0.4406 -0.5538 0.216 Uiso 1 1 calc R . . C2 C -1.337(4) -0.388(2) -0.4569(10) 0.131(10) Uani 1 1 d . . . H2A H -1.4618 -0.3904 -0.4592 0.196 Uiso 1 1 calc R . . H2B H -1.2952 -0.3225 -0.4727 0.196 Uiso 1 1 calc R . . H2C H -1.3036 -0.3876 -0.4230 0.196 Uiso 1 1 calc R . . C3 C -1.261(3) -0.4896(16) -0.4821(7) 0.080(6) Uani 1 1 d . . . H3A H -1.3057 -0.5548 -0.4649 0.096 Uiso 1 1 calc R . . C4 C -1.066(3) -0.4935(15) -0.4788(6) 0.067(5) Uani 1 1 d . . . H4A H -1.0236 -0.5595 -0.4959 0.081 Uiso 1 1 calc R . . C5 C -0.970(3) -0.392(2) -0.4984(7) 0.108(8) Uani 1 1 d . . . H5A H -0.8749 -0.4138 -0.5195 0.130 Uiso 1 1 calc R . . H5B H -1.0484 -0.3448 -0.5168 0.130 Uiso 1 1 calc R . . C6 C -0.924(2) -0.4107(13) -0.4181(5) 0.055(4) Uani 1 1 d . . . C7 C -0.849(2) -0.3892(15) -0.3706(5) 0.060(4) Uani 1 1 d . . . C8 C -0.769(3) -0.2942(16) -0.3556(7) 0.076(6) Uani 1 1 d . . . H8A H -0.7604 -0.2343 -0.3768 0.091 Uiso 1 1 calc R . . C9 C -0.702(3) -0.2872(19) -0.3091(8) 0.092(7) Uani 1 1 d . . . H9A H -0.6453 -0.2234 -0.2987 0.110 Uiso 1 1 calc R . . C10 C -0.718(3) -0.3731(16) -0.2793(6) 0.074(6) Uani 1 1 d . . . H10A H -0.6794 -0.3697 -0.2470 0.089 Uiso 1 1 calc R . . C11 C -0.794(3) -0.4673(14) -0.2975(5) 0.060(4) Uani 1 1 d . . . H11A H -0.7991 -0.5284 -0.2768 0.072 Uiso 1 1 calc R . . C12 C -0.969(3) -0.7650(15) -0.3276(8) 0.074(5) Uani 1 1 d . . . C13 C -1.058(3) -0.6840(16) -0.3022(6) 0.070(5) Uani 1 1 d . . . H13A H -1.0060 -0.6536 -0.2723 0.084 Uiso 1 1 calc R . . C14 C -1.198(3) -0.6309(15) -0.3221(7) 0.075(5) Uani 1 1 d . . . C15 C -1.250(2) -0.6632(13) -0.3710(5) 0.055(4) Uani 1 1 d . . . H15A H -1.3329 -0.6157 -0.3884 0.066 Uiso 1 1 calc R . . C16 C -1.170(3) -0.7421(14) -0.3966(6) 0.066(5) Uani 1 1 d . . . C17 C -1.027(2) -0.7949(12) -0.3741(7) 0.068(4) Uani 1 1 d . . . H17A H -0.9512 -0.8411 -0.3945 0.081 Uiso 1 1 calc R . . C18 C -0.802(4) -0.8198(18) -0.3040(10) 0.119(10) Uani 1 1 d . . . H18A H -0.8354 -0.8852 -0.2864 0.179 Uiso 1 1 calc R . . H18B H -0.7488 -0.7684 -0.2817 0.179 Uiso 1 1 calc R . . H18C H -0.7213 -0.8389 -0.3294 0.179 Uiso 1 1 calc R . . C19 C -1.291(4) -0.537(2) -0.2948(9) 0.115(9) Uani 1 1 d . . . H19A H -1.3822 -0.5667 -0.2748 0.172 Uiso 1 1 calc R . . H19B H -1.3396 -0.4860 -0.3182 0.172 Uiso 1 1 calc R . . H19C H -1.2092 -0.4984 -0.2744 0.172 Uiso 1 1 calc R . . C20 C -1.227(3) -0.7817(16) -0.4467(7) 0.084(6) Uani 1 1 d . . . H20A H -1.3164 -0.8363 -0.4431 0.125 Uiso 1 1 calc R . . H20B H -1.1297 -0.8135 -0.4637 0.125 Uiso 1 1 calc R . . H20C H -1.2710 -0.7203 -0.4653 0.125 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 Sb1 0.0812(9) 0.1148(11) 0.0509(6) -0.0058(7) -0.0012(6) 0.0405(9) F1 0.105(11) 0.220(18) 0.113(10) 0.023(12) -0.015(9) 0.052(13) F2 0.130(12) 0.173(15) 0.095(8) 0.047(10) 0.030(8) 0.070(12) F3 0.112(11) 0.24(2) 0.096(9) -0.025(11) -0.025(8) 0.085(13) F4 0.21(2) 0.50(5) 0.080(9) -0.001(18) 0.049(12) 0.18(3) F5 0.23(3) 0.112(13) 0.32(3) 0.062(17) -0.07(3) -0.045(16) F6 0.24(3) 0.141(15) 0.28(3) -0.055(18) -0.03(2) 0.008(19) Ru1 0.0401(6) 0.0479(6) 0.0407(5) -0.0008(5) -0.0032(5) -0.0039(5) Br1 0.0462(9) 0.1065(16) 0.0872(13) -0.0183(12) 0.0071(9) 0.0056(10) O1 0.141(13) 0.083(9) 0.062(7) 0.031(7) -0.011(8) -0.045(10) N1 0.047(6) 0.050(6) 0.035(5) 0.011(5) 0.001(5) 0.003(6) N2 0.044(7) 0.072(9) 0.044(6) 0.001(7) -0.006(6) -0.016(7) C1 0.18(3) 0.14(2) 0.115(19) 0.029(19) -0.08(2) 0.00(2) C2 0.14(2) 0.109(19) 0.14(2) 0.00(2) -0.05(2) 0.05(2) C3 0.092(14) 0.062(11) 0.085(13) 0.001(10) -0.044(12) -0.025(11) C4 0.098(14) 0.063(10) 0.041(8) -0.004(8) -0.007(9) -0.005(11) C5 0.13(2) 0.120(17) 0.070(11) 0.034(13) -0.027(13) -0.049(19) C6 0.076(10) 0.051(9) 0.038(7) 0.005(7) -0.008(7) -0.020(8) C7 0.064(9) 0.066(9) 0.050(7) 0.011(9) -0.016(8) -0.020(9) C8 0.083(14) 0.063(11) 0.082(13) 0.005(9) -0.009(11) -0.029(11) C9 0.095(16) 0.089(14) 0.092(14) -0.018(12) -0.013(13) -0.058(14) C10 0.086(13) 0.092(14) 0.044(8) -0.017(9) 0.002(8) -0.039(14) C11 0.079(12) 0.059(10) 0.042(7) -0.002(7) -0.017(8) -0.020(10) C12 0.069(12) 0.064(10) 0.090(12) 0.011(10) -0.036(11) -0.018(10) C13 0.087(14) 0.078(12) 0.046(8) 0.008(9) 0.005(9) -0.030(12) C14 0.081(12) 0.063(11) 0.082(11) 0.019(10) 0.030(11) -0.017(11) C15 0.071(10) 0.066(9) 0.027(6) -0.007(7) -0.005(7) -0.016(8) C16 0.084(12) 0.061(10) 0.052(9) -0.004(8) -0.017(9) -0.019(10) C17 0.062(10) 0.043(7) 0.097(12) -0.013(9) -0.005(11) 0.004(8) C18 0.14(2) 0.071(13) 0.15(2) 0.052(15) -0.050(19) 0.016(16) C19 0.12(2) 0.108(18) 0.119(18) -0.036(16) 0.061(17) -0.005(17) C20 0.099(15) 0.071(12) 0.080(12) -0.012(10) -0.036(12) -0.015(12) _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 Sb1 F5 1.791(19) . ? Sb1 F4 1.796(15) . ? Sb1 F2 1.824(13) . ? Sb1 F3 1.825(13) . ? Sb1 F1 1.850(15) . ? Sb1 F6 1.90(2) . ? Ru1 N1 2.096(10) . ? Ru1 N2 2.097(13) . ? Ru1 C15 2.162(17) . ? Ru1 C13 2.164(16) . ? Ru1 C12 2.166(18) . ? Ru1 C14 2.181(17) . ? Ru1 C17 2.183(15) . ? Ru1 C16 2.209(17) . ? Ru1 Br1 2.522(2) . ? O1 C6 1.355(18) . ? O1 C5 1.45(2) . ? N1 C6 1.227(18) . ? N1 C4 1.488(18) . ? N2 C11 1.305(18) . ? N2 C7 1.338(19) . ? C1 C3 1.51(3) . ? C2 C3 1.53(3) . ? C3 C4 1.51(3) . ? C4 C5 1.53(3) . ? C6 C7 1.441(19) . ? C7 C8 1.37(2) . ? C8 C9 1.37(3) . ? C9 C10 1.32(3) . ? C10 C11 1.37(2) . ? C12 C13 1.38(3) . ? C12 C17 1.39(2) . ? C12 C18 1.58(3) . ? C13 C14 1.37(3) . ? C14 C15 1.44(2) . ? C14 C19 1.54(3) . ? C15 C16 1.33(2) . ? C16 C17 1.41(3) . ? C16 C20 1.51(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 F5 Sb1 F4 92.9(16) . . ? F5 Sb1 F2 90.0(12) . . ? F4 Sb1 F2 177.0(13) . . ? F5 Sb1 F3 88.5(11) . . ? F4 Sb1 F3 89.2(8) . . ? F2 Sb1 F3 91.6(7) . . ? F5 Sb1 F1 90.1(11) . . ? F4 Sb1 F1 90.8(9) . . ? F2 Sb1 F1 88.4(7) . . ? F3 Sb1 F1 178.6(10) . . ? F5 Sb1 F6 176.9(12) . . ? F4 Sb1 F6 89.2(14) . . ? F2 Sb1 F6 87.8(10) . . ? F3 Sb1 F6 93.8(11) . . ? F1 Sb1 F6 87.6(11) . . ? N1 Ru1 N2 76.4(5) . . ? N1 Ru1 C15 95.9(5) . . ? N2 Ru1 C15 128.7(5) . . ? N1 Ru1 C13 149.5(7) . . ? N2 Ru1 C13 94.0(6) . . ? C15 Ru1 C13 67.4(7) . . ? N1 Ru1 C12 168.5(6) . . ? N2 Ru1 C12 114.8(6) . . ? C15 Ru1 C12 79.2(7) . . ? C13 Ru1 C12 37.3(7) . . ? N1 Ru1 C14 115.2(6) . . ? N2 Ru1 C14 98.7(6) . . ? C15 Ru1 C14 38.8(7) . . ? C13 Ru1 C14 36.7(8) . . ? C12 Ru1 C14 67.2(8) . . ? N1 Ru1 C17 131.3(6) . . ? N2 Ru1 C17 150.8(6) . . ? C15 Ru1 C17 65.4(7) . . ? C13 Ru1 C17 66.5(7) . . ? C12 Ru1 C17 37.2(7) . . ? C14 Ru1 C17 78.9(7) . . ? N1 Ru1 C16 101.9(6) . . ? N2 Ru1 C16 164.2(6) . . ? C15 Ru1 C16 35.5(6) . . ? C13 Ru1 C16 79.6(7) . . ? C12 Ru1 C16 68.1(6) . . ? C14 Ru1 C16 67.6(7) . . ? C17 Ru1 C16 37.6(7) . . ? N1 Ru1 Br1 82.9(3) . . ? N2 Ru1 Br1 85.6(4) . . ? C15 Ru1 Br1 144.6(4) . . ? C13 Ru1 Br1 125.7(6) . . ? C12 Ru1 Br1 95.0(6) . . ? C14 Ru1 Br1 161.8(6) . . ? C17 Ru1 Br1 88.8(5) . . ? C16 Ru1 Br1 109.9(5) . . ? C6 O1 C5 104.9(13) . . ? C6 N1 C4 109.3(12) . . ? C6 N1 Ru1 113.7(9) . . ? C4 N1 Ru1 135.6(10) . . ? C11 N2 C7 116.2(14) . . ? C11 N2 Ru1 128.2(12) . . ? C7 N2 Ru1 115.6(9) . . ? C4 C3 C1 109(2) . . ? C4 C3 C2 112.5(17) . . ? C1 C3 C2 113(2) . . ? N1 C4 C3 112.1(15) . . ? N1 C4 C5 101.2(14) . . ? C3 C4 C5 115.8(19) . . ? O1 C5 C4 104.7(14) . . ? N1 C6 O1 117.8(13) . . ? N1 C6 C7 122.0(13) . . ? O1 C6 C7 120.2(13) . . ? N2 C7 C8 121.6(14) . . ? N2 C7 C6 111.4(14) . . ? C8 C7 C6 127.0(15) . . ? C7 C8 C9 119.9(17) . . ? C10 C9 C8 118.8(17) . . ? C9 C10 C11 118.1(15) . . ? N2 C11 C10 125.2(16) . . ? C13 C12 C17 118.7(17) . . ? C13 C12 C18 119.8(19) . . ? C17 C12 C18 122(2) . . ? C13 C12 Ru1 71.3(10) . . ? C17 C12 Ru1 72.0(10) . . ? C18 C12 Ru1 127.3(14) . . ? C14 C13 C12 121.8(17) . . ? C14 C13 Ru1 72.3(10) . . ? C12 C13 Ru1 71.5(10) . . ? C13 C14 C15 117.2(18) . . ? C13 C14 C19 122(2) . . ? C15 C14 C19 121(2) . . ? C13 C14 Ru1 71.0(11) . . ? C15 C14 Ru1 69.9(10) . . ? C19 C14 Ru1 127.3(13) . . ? C16 C15 C14 123.1(17) . . ? C16 C15 Ru1 74.1(11) . . ? C14 C15 Ru1 71.3(10) . . ? C15 C16 C17 117.4(15) . . ? C15 C16 C20 124.2(18) . . ? C17 C16 C20 118.4(18) . . ? C15 C16 Ru1 70.3(10) . . ? C17 C16 Ru1 70.2(9) . . ? C20 C16 Ru1 132.8(13) . . ? C12 C17 C16 121.8(17) . . ? C12 C17 Ru1 70.7(9) . . ? C16 C17 Ru1 72.2(9) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.344 _refine_diff_density_min -0.900 _refine_diff_density_rms 0.150 #===END data_2b _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H26 Br F6 N2 O Ru Sb' _chemical_formula_weight 727.16 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ru' 'Ru' -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sb' 'Sb' -0.5866 1.5461 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5892(9) _cell_length_b 9.5732(14) _cell_length_c 29.369(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2414.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 59 _cell_measurement_theta_min 5.32 _cell_measurement_theta_max 12.49 _exptl_crystal_description tablet _exptl_crystal_colour orange _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.000 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 3.460 _exptl_absorpt_correction_type 'analytical (SHELXTL/PC)' _exptl_absorpt_correction_T_min 0.273 _exptl_absorpt_correction_T_max 0.411 _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(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 'Siemens P4 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2 _diffrn_reflns_number 3782 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3570 _reflns_number_observed 3311 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXTL/PC ver5.0 (Sheldrick, 1996)' _computing_structure_refinement 'SHELXTL/PC ver5.0 (Sheldrick, 1996)' _computing_molecular_graphics 'SHELXTL/PC ver5.0 (Sheldrick, 1996)' _computing_publication_material 'SHELXTL/PC ver5.0 (Sheldrick, 1996)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0340P)^2^+44.9165P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 3569 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_obs 0.0534 _refine_ls_wR_factor_all 0.1364 _refine_ls_wR_factor_obs 0.1326 _refine_ls_goodness_of_fit_all 1.090 _refine_ls_goodness_of_fit_obs 1.105 _refine_ls_restrained_S_all 1.092 _refine_ls_restrained_S_obs 1.105 _refine_ls_shift/esd_max 0.011 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ru1 Ru 0.51448(11) 0.69332(10) 0.63734(3) 0.0228(2) Uani 1 d . . Br1 Br 0.4181(2) 0.8289(2) 0.56891(4) 0.0364(3) Uani 1 d . . O1 O 0.6787(11) 0.3886(10) 0.5485(3) 0.034(2) Uani 1 d . . N1 N 0.5294(12) 0.5116(11) 0.5962(3) 0.026(2) Uani 1 d . . N2 N 0.7293(12) 0.7157(12) 0.6037(3) 0.028(2) Uani 1 d . . C1 C 0.3083(18) 0.4774(17) 0.5140(4) 0.039(3) Uani 1 d . . H1A H 0.3758(18) 0.5571(17) 0.5159(4) 0.058 Uiso 1 calc R . H1B H 0.2099(18) 0.5052(17) 0.5015(4) 0.058 Uiso 1 calc R . H1C H 0.3549(18) 0.4079(17) 0.4948(4) 0.058 Uiso 1 calc R . C2 C 0.1795(16) 0.2925(14) 0.5615(5) 0.035(3) Uani 1 d . . H2A H 0.0849(16) 0.3150(14) 0.5457(5) 0.053 Uiso 1 calc R . H2B H 0.1556(16) 0.2658(14) 0.5922(5) 0.053 Uiso 1 calc R . H2C H 0.2307(16) 0.2165(14) 0.5463(5) 0.053 Uiso 1 calc R . C3 C 0.2833(15) 0.4163(15) 0.5619(4) 0.029(3) Uani 1 d . . H3A H 0.2294(15) 0.4884(15) 0.5796(4) 0.035 Uiso 1 calc R . C4 C 0.4378(15) 0.3873(14) 0.5868(4) 0.029(3) Uani 1 d . . H4A H 0.4138(15) 0.3421(14) 0.6159(4) 0.034 Uiso 1 calc R . C5 C 0.5527(15) 0.2922(14) 0.5603(5) 0.036(3) Uani 1 d . . H5A H 0.5902(15) 0.2164(14) 0.5793(5) 0.043 Uiso 1 calc R . H5B H 0.5044(15) 0.2535(14) 0.5333(5) 0.043 Uiso 1 calc R . C6 C 0.6559(16) 0.5037(14) 0.5730(4) 0.028(3) Uani 1 d . . C7 C 0.7673(15) 0.6116(15) 0.5752(4) 0.028(3) Uani 1 d . . C8 C 0.9049(16) 0.6143(16) 0.5492(4) 0.034(3) Uani 1 d . . H8A H 0.9283(16) 0.5419(16) 0.5292(4) 0.041 Uiso 1 calc R . C9 C 1.0040(15) 0.7264(15) 0.5539(4) 0.036(3) Uani 1 d . . H9A H 1.0972(15) 0.7290(15) 0.5377(4) 0.043 Uiso 1 calc R . C10 C 0.9651(15) 0.8342(14) 0.5824(5) 0.033(3) Uani 1 d . . H10A H 1.0308(15) 0.9111(14) 0.5849(5) 0.040 Uiso 1 calc R . C11 C 0.8284(14) 0.8296(15) 0.6076(4) 0.030(3) Uani 1 d . . H11A H 0.8033(14) 0.9028(15) 0.6271(4) 0.037 Uiso 1 calc R . C12 C 0.3955(18) 0.8472(15) 0.6826(4) 0.034(3) Uani 1 d . . C13 C 0.5584(16) 0.8387(16) 0.6953(4) 0.030(3) Uani 1 d . . H13A H 0.6264(16) 0.9198(16) 0.6910(4) 0.036 Uiso 1 calc R . C14 C 0.6259(14) 0.7027(12) 0.7045(4) 0.023(2) Uani 1 d . . C15 C 0.5314(17) 0.5879(14) 0.7027(4) 0.030(3) Uani 1 d . . H15A H 0.5812(17) 0.4958(14) 0.7033(4) 0.036 Uiso 1 calc R . C16 C 0.3690(18) 0.5936(16) 0.6910(4) 0.034(3) Uani 1 d . . C17 C 0.3062(15) 0.7253(17) 0.6793(4) 0.038(3) Uani 1 d . . H17A H 0.2041(15) 0.7295(17) 0.6645(4) 0.045 Uiso 1 calc R . C18 C 0.3277(22) 0.9871(17) 0.6717(6) 0.056(5) Uani 1 d . . H18A H 0.4056(22) 1.0579(17) 0.6758(6) 0.084 Uiso 1 calc R . H18B H 0.2414(22) 1.0055(17) 0.6916(6) 0.084 Uiso 1 calc R . H18C H 0.2924(22) 0.9879(17) 0.6407(6) 0.084 Uiso 1 calc R . C19 C 0.7955(18) 0.6961(23) 0.7158(5) 0.056(5) Uani 1 d . . H19A H 0.8388(18) 0.7886(23) 0.7151(5) 0.084 Uiso 1 calc R . H19B H 0.8481(18) 0.6384(23) 0.6940(5) 0.084 Uiso 1 calc R . H19C H 0.8085(18) 0.6572(23) 0.7457(5) 0.084 Uiso 1 calc R . C20 C 0.2660(23) 0.4681(18) 0.6900(5) 0.051(5) Uani 1 d . . H20A H 0.3248(23) 0.3870(18) 0.6987(5) 0.077 Uiso 1 calc R . H20B H 0.2256(23) 0.4555(18) 0.6599(5) 0.077 Uiso 1 calc R . H20C H 0.1813(23) 0.4809(18) 0.7110(5) 0.077 Uiso 1 calc R . Sb1 Sb 1.14950(10) 0.73691(9) 0.82402(3) 0.0311(2) Uani 1 d . . F1 F 0.9363(9) 0.7143(9) 0.8256(3) 0.046(2) Uani 1 d . . F2 F 1.1387(14) 0.8281(11) 0.7681(3) 0.060(3) Uani 1 d . . F3 F 1.1669(14) 0.5634(10) 0.7956(3) 0.060(3) Uani 1 d . . F4 F 1.1641(14) 0.6460(10) 0.8805(3) 0.061(3) Uani 1 d . . F5 F 1.3695(11) 0.7539(14) 0.8232(5) 0.087(4) Uani 1 d . . F6 F 1.1330(13) 0.9091(9) 0.8536(3) 0.053(2) Uani 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 Ru1 0.0220(4) 0.0260(5) 0.0204(4) -0.0027(4) 0.0004(4) -0.0020(4) Br1 0.0325(7) 0.0441(8) 0.0325(6) 0.0061(6) -0.0029(6) 0.0045(7) O1 0.030(5) 0.037(5) 0.035(5) -0.011(4) 0.002(4) -0.002(5) N1 0.017(5) 0.035(6) 0.025(5) -0.001(4) -0.002(4) -0.008(5) N2 0.020(5) 0.038(6) 0.024(5) 0.005(5) 0.001(4) -0.005(5) C1 0.033(8) 0.054(9) 0.030(7) 0.002(7) -0.001(6) -0.008(7) C2 0.039(7) 0.028(7) 0.038(7) -0.004(6) -0.004(6) -0.007(6) C3 0.023(6) 0.035(7) 0.029(6) 0.004(6) 0.000(5) -0.007(6) C4 0.025(6) 0.033(7) 0.028(6) -0.001(5) 0.000(5) -0.006(6) C5 0.034(7) 0.028(7) 0.045(7) -0.008(6) -0.012(6) -0.010(6) C6 0.026(6) 0.037(7) 0.021(5) -0.002(5) 0.000(5) 0.014(6) C7 0.028(6) 0.039(7) 0.019(5) 0.004(5) -0.001(5) 0.009(6) C8 0.027(7) 0.047(8) 0.028(6) -0.001(6) 0.007(5) 0.015(7) C9 0.017(5) 0.048(8) 0.042(7) 0.006(6) 0.002(5) -0.001(7) C10 0.025(6) 0.026(6) 0.049(7) 0.007(6) -0.004(6) -0.003(6) C11 0.021(6) 0.037(7) 0.033(6) 0.002(6) -0.004(5) -0.018(6) C12 0.042(8) 0.034(7) 0.026(6) -0.011(6) 0.000(6) 0.016(6) C13 0.029(7) 0.038(7) 0.023(6) -0.012(5) 0.002(5) 0.002(6) C14 0.031(6) 0.022(6) 0.017(5) -0.003(4) -0.003(5) 0.000(5) C15 0.041(8) 0.032(7) 0.018(5) -0.002(5) 0.004(6) 0.005(7) C16 0.035(8) 0.046(8) 0.020(6) -0.004(6) -0.003(6) -0.003(7) C17 0.025(6) 0.064(10) 0.024(6) -0.003(7) 0.006(5) 0.000(7) C18 0.055(11) 0.053(9) 0.059(10) -0.013(9) -0.006(10) 0.024(9) C19 0.048(9) 0.088(14) 0.032(7) -0.016(9) -0.018(7) -0.001(11) C20 0.068(12) 0.057(10) 0.029(7) -0.011(7) 0.022(8) -0.018(10) Sb1 0.0286(4) 0.0250(4) 0.0398(5) -0.0010(4) -0.0041(4) 0.0016(4) F1 0.033(4) 0.053(5) 0.053(5) -0.009(5) -0.001(4) -0.023(4) F2 0.085(7) 0.061(6) 0.035(4) 0.011(4) 0.009(5) -0.003(7) F3 0.075(7) 0.040(5) 0.066(6) -0.019(5) 0.001(6) 0.021(6) F4 0.083(8) 0.047(5) 0.052(5) 0.014(4) -0.023(6) -0.004(6) F5 0.031(5) 0.096(8) 0.133(10) 0.000(10) -0.001(6) -0.007(6) F6 0.075(7) 0.036(4) 0.047(5) -0.006(4) -0.016(5) -0.009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru1 N2 2.103(10) . ? Ru1 N1 2.122(11) . ? Ru1 C15 2.174(12) . ? Ru1 C14 2.193(11) . ? Ru1 C17 2.194(12) . ? Ru1 C16 2.227(14) . ? Ru1 C13 2.231(12) . ? Ru1 C12 2.233(12) . ? Ru1 Br1 2.532(2) . ? O1 C6 1.33(2) . ? O1 C5 1.46(2) . ? N1 C6 1.28(2) . ? N1 C4 1.45(2) . ? N2 C7 1.34(2) . ? N2 C11 1.39(2) . ? C1 C3 1.54(2) . ? C2 C3 1.48(2) . ? C3 C4 1.54(2) . ? C4 C5 1.55(2) . ? C6 C7 1.41(2) . ? C7 C8 1.41(2) . ? C8 C9 1.38(2) . ? C9 C10 1.37(2) . ? C10 C11 1.39(2) . ? C12 C17 1.40(2) . ? C12 C13 1.45(2) . ? C12 C18 1.50(2) . ? C13 C14 1.45(2) . ? C14 C15 1.37(2) . ? C14 C19 1.50(2) . ? C15 C16 1.44(2) . ? C16 C17 1.41(2) . ? C16 C20 1.49(2) . ? Sb1 F1 1.844(8) . ? Sb1 F2 1.863(8) . ? Sb1 F3 1.864(9) . ? Sb1 F6 1.869(9) . ? Sb1 F4 1.877(9) . ? Sb1 F5 1.897(10) . ? 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 N2 Ru1 N1 76.3(4) . . ? N2 Ru1 C15 113.8(5) . . ? N1 Ru1 C15 96.8(4) . . ? N2 Ru1 C14 92.0(4) . . ? N1 Ru1 C14 121.3(4) . . ? C15 Ru1 C14 36.5(5) . . ? N2 Ru1 C17 164.7(5) . . ? N1 Ru1 C17 118.9(5) . . ? C15 Ru1 C17 67.8(5) . . ? C14 Ru1 C17 81.1(5) . . ? N2 Ru1 C16 150.2(5) . . ? N1 Ru1 C16 94.9(5) . . ? C15 Ru1 C16 38.1(5) . . ? C14 Ru1 C16 68.0(5) . . ? C17 Ru1 C16 37.3(5) . . ? N2 Ru1 C13 98.4(5) . . ? N1 Ru1 C13 159.4(5) . . ? C15 Ru1 C13 66.7(5) . . ? C14 Ru1 C13 38.3(5) . . ? C17 Ru1 C13 67.8(5) . . ? C16 Ru1 C13 79.7(5) . . ? N2 Ru1 C12 127.9(5) . . ? N1 Ru1 C12 155.2(5) . . ? C15 Ru1 C12 79.1(5) . . ? C14 Ru1 C12 68.7(5) . . ? C17 Ru1 C12 36.9(6) . . ? C16 Ru1 C12 66.7(5) . . ? C13 Ru1 C12 37.9(5) . . ? N2 Ru1 Br1 82.1(3) . . ? N1 Ru1 Br1 89.3(3) . . ? C15 Ru1 Br1 163.9(4) . . ? C14 Ru1 Br1 146.7(3) . . ? C17 Ru1 Br1 96.2(4) . . ? C16 Ru1 Br1 126.7(4) . . ? C13 Ru1 Br1 110.0(4) . . ? C12 Ru1 Br1 89.1(4) . . ? C6 O1 C5 106.6(10) . . ? C6 N1 C4 108.0(11) . . ? C6 N1 Ru1 113.6(9) . . ? C4 N1 Ru1 138.3(8) . . ? C7 N2 C11 119.0(11) . . ? C7 N2 Ru1 115.5(9) . . ? C11 N2 Ru1 125.4(9) . . ? C2 C3 C4 112.2(11) . . ? C2 C3 C1 112.3(11) . . ? C4 C3 C1 112.4(11) . . ? N1 C4 C3 114.1(11) . . ? N1 C4 C5 103.4(10) . . ? C3 C4 C5 114.6(11) . . ? O1 C5 C4 102.6(10) . . ? N1 C6 O1 117.3(13) . . ? N1 C6 C7 120.5(12) . . ? O1 C6 C7 122.1(12) . . ? N2 C7 C6 114.0(11) . . ? N2 C7 C8 122.0(13) . . ? C6 C7 C8 123.9(12) . . ? C9 C8 C7 118.6(13) . . ? C8 C9 C10 119.8(12) . . ? C11 C10 C9 120.5(12) . . ? C10 C11 N2 120.0(12) . . ? C17 C12 C13 119.9(13) . . ? C17 C12 C18 121.3(14) . . ? C13 C12 C18 118.8(15) . . ? C17 C12 Ru1 70.1(7) . . ? C13 C12 Ru1 71.0(7) . . ? C18 C12 Ru1 129.9(11) . . ? C12 C13 C14 118.9(13) . . ? C12 C13 Ru1 71.1(7) . . ? C14 C13 Ru1 69.5(7) . . ? C15 C14 C13 118.5(11) . . ? C15 C14 C19 123.6(14) . . ? C13 C14 C19 117.9(13) . . ? C15 C14 Ru1 71.0(7) . . ? C13 C14 Ru1 72.3(6) . . ? C19 C14 Ru1 128.6(9) . . ? C14 C15 C16 123.7(13) . . ? C14 C15 Ru1 72.5(7) . . ? C16 C15 Ru1 73.0(8) . . ? C17 C16 C15 117.5(14) . . ? C17 C16 C20 119.2(14) . . ? C15 C16 C20 123.3(15) . . ? C17 C16 Ru1 70.1(8) . . ? C15 C16 Ru1 68.9(8) . . ? C20 C16 Ru1 131.6(9) . . ? C12 C17 C16 121.2(12) . . ? C12 C17 Ru1 73.0(7) . . ? C16 C17 Ru1 72.6(8) . . ? F1 Sb1 F2 91.6(5) . . ? F1 Sb1 F3 89.2(5) . . ? F2 Sb1 F3 91.6(5) . . ? F1 Sb1 F6 91.0(4) . . ? F2 Sb1 F6 89.6(4) . . ? F3 Sb1 F6 178.8(4) . . ? F1 Sb1 F4 89.4(5) . . ? F2 Sb1 F4 179.0(5) . . ? F3 Sb1 F4 88.6(4) . . ? F6 Sb1 F4 90.2(4) . . ? F1 Sb1 F5 178.0(5) . . ? F2 Sb1 F5 89.9(5) . . ? F3 Sb1 F5 89.5(6) . . ? F6 Sb1 F5 90.3(6) . . ? F4 Sb1 F5 89.1(5) . . ? _refine_diff_density_max 1.134 _refine_diff_density_min -2.099 _refine_diff_density_rms 0.201