# Copyright The Royal Society of Chemistry, 1998 # MANUSCRIPT 8/04717K data_glaser1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H23 F4 N2 O7 Re S2' _chemical_formula_weight 729.72 _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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Re' 'Re' -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.093(2) _cell_length_b 11.506(2) _cell_length_c 17.288(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.390(10) _cell_angle_gamma 90.00 _cell_volume 2592.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 349 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 25 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method ? _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 4.920 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'MSC/Rigaku Raxis-IIc' _diffrn_measurement_method 'oscilation diffraction' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15143 _diffrn_reflns_av_R_equivalents 0.0799 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.34 _reflns_number_total 4704 _reflns_number_observed 3416 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MSC datacollection Software' _computing_cell_refinement 'Denzo/Scalepack Version 1.9.0' _computing_data_reduction Shelx97 _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL-PLUS, XP' _computing_publication_material 'SHELXTL-PLUS, XCIF' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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^)+(0.0497P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4704 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_obs 0.0393 _refine_ls_wR_factor_all 0.0965 _refine_ls_wR_factor_obs 0.0883 _refine_ls_goodness_of_fit_all 0.971 _refine_ls_goodness_of_fit_obs 1.056 _refine_ls_restrained_S_all 0.971 _refine_ls_restrained_S_obs 1.056 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Re1 Re 0.64343(2) 0.20595(2) 0.10998(2) 0.04741(13) Uani 1 d . . S2 S 0.69813(14) 0.1234(2) 0.24487(10) 0.0579(4) Uani 1 d . . S1 S 0.5078(2) 0.27501(15) 0.13783(12) 0.0601(5) Uani 1 d . . N2 N 0.5531(4) 0.2038(4) -0.0133(3) 0.0520(13) Uani 1 d . . N1 N 0.6642(4) 0.0445(5) 0.0787(3) 0.0516(13) Uani 1 d . . F1 F 0.4876(4) 0.5254(4) -0.3728(3) 0.101(2) Uani 1 d . . F2 F 0.3706(4) 0.5131(5) -0.5374(3) 0.103(2) Uani 1 d . . F3 F 0.3561(6) 0.1057(5) -0.5164(4) 0.138(2) Uani 1 d . . F4 F 0.4687(5) 0.1172(5) -0.3520(4) 0.115(2) Uani 1 d . . O1 O 0.7352(4) 0.3053(4) 0.1206(3) 0.0620(13) Uani 1 d . . O2 O 0.7355(4) -0.1362(4) 0.1127(3) 0.080(2) Uani 1 d . . O3 O 0.5217(4) 0.1067(4) -0.1370(3) 0.0703(14) Uani 1 d . . O4 O 0.4180(5) 0.4012(6) -0.2468(3) 0.088(2) Uani 1 d . . O5 O 0.5465(4) 0.3268(6) -0.2765(3) 0.085(2) Uani 1 d . . O7 O 0.7817(7) 0.1873(8) -0.2380(5) 0.136(3) Uani 1 d . . C17 C 0.6775(12) 0.1893(10) -0.4934(7) 0.149(6) Uani 1 d . . H17A H 0.6920(12) 0.2553(10) -0.5211(7) 0.223 Uiso 1 calc R . H17B H 0.6047(12) 0.1771(10) -0.5137(7) 0.223 Uiso 1 calc R . H17C H 0.7101(12) 0.1216(10) -0.5045(7) 0.223 Uiso 1 calc R . C18 C 0.7168(9) 0.2105(8) -0.4032(6) 0.098(3) Uani 1 d . . H18A H 0.6846(9) 0.2790(8) -0.3914(6) 0.117 Uiso 1 calc R . H18B H 0.7904(9) 0.2233(8) -0.3822(6) 0.117 Uiso 1 calc R . O6 O 0.6937(5) 0.1086(5) -0.3627(4) 0.096(2) Uani 1 d . . C19 C 0.7312(8) 0.1086(10) -0.2799(6) 0.089(3) Uani 1 d . . C20 C 0.6989(9) 0.0003(9) -0.2476(7) 0.122(4) Uani 1 d . . H20A H 0.6594(9) -0.0482(9) -0.2939(7) 0.182 Uiso 1 calc R . H20B H 0.6580(9) 0.0212(9) -0.2163(7) 0.182 Uiso 1 calc R . H20C H 0.7587(9) -0.0413(9) -0.2121(7) 0.182 Uiso 1 calc R . C1 C 0.5355(6) 0.2405(7) 0.2482(5) 0.067(2) Uani 1 d . . H1B H 0.5823(6) 0.2979(7) 0.2838(5) 0.081 Uiso 1 calc R . H1C H 0.4725(6) 0.2429(7) 0.2585(5) 0.081 Uiso 1 calc R . C2 C 0.5830(6) 0.1210(6) 0.2687(4) 0.062(2) Uani 1 d . . H2A H 0.5355(6) 0.0625(6) 0.2353(4) 0.075 Uiso 1 calc R . H2B H 0.6004(6) 0.1034(6) 0.3274(4) 0.075 Uiso 1 calc R . C3 C 0.7200(6) -0.0266(6) 0.2231(4) 0.061(2) Uani 1 d . . H3A H 0.7881(6) -0.0499(6) 0.2607(4) 0.074 Uiso 1 calc R . H3B H 0.6707(6) -0.0761(6) 0.2341(4) 0.074 Uiso 1 calc R . C4 C 0.7105(6) -0.0449(6) 0.1342(4) 0.060(2) Uani 1 d . . C5 C 0.6322(5) 0.0171(5) -0.0094(4) 0.052(2) Uani 1 d . . H5A H 0.5951(5) -0.0561(5) -0.0213(4) 0.062 Uiso 1 calc R . H5B H 0.6919(5) 0.0091(5) -0.0239(4) 0.062 Uiso 1 calc R . C6 C 0.5636(5) 0.1134(6) -0.0611(4) 0.053(2) Uani 1 d . . C7 C 0.4824(6) 0.2975(6) -0.0570(5) 0.064(2) Uani 1 d . . H7A H 0.4431(6) 0.3207(6) -0.0241(5) 0.076 Uiso 1 calc R . H7B H 0.4346(6) 0.2687(6) -0.1103(5) 0.076 Uiso 1 calc R . C8 C 0.5381(7) 0.4032(6) -0.0720(5) 0.073(2) Uani 1 d . . H8A H 0.4903(7) 0.4677(6) -0.0896(5) 0.087 Uiso 1 calc R . H8B H 0.5925(7) 0.4249(6) -0.0197(5) 0.087 Uiso 1 calc R . C9 C 0.5836(6) 0.3838(7) -0.1367(4) 0.074(2) Uani 1 d . . H9A H 0.6282(6) 0.4486(7) -0.1354(4) 0.088 Uiso 1 calc R . H9B H 0.6253(6) 0.3140(7) -0.1226(4) 0.088 Uiso 1 calc R . C10 C 0.5051(7) 0.3718(7) -0.2230(5) 0.068(2) Uani 1 d . . C11 C 0.4804(6) 0.3210(8) -0.3597(5) 0.072(2) Uani 1 d . . C12 C 0.4553(7) 0.4201(7) -0.4069(6) 0.075(2) Uani 1 d . . C13 C 0.3950(7) 0.4129(8) -0.4930(5) 0.080(2) Uani 1 d . . C14 C 0.3621(7) 0.3088(8) -0.5316(6) 0.082(2) Uani 1 d . . H14A H 0.3242(7) 0.3043(8) -0.5889(6) 0.098 Uiso 1 calc R . C15 C 0.3872(8) 0.2107(8) -0.4823(6) 0.088(3) Uani 1 d . . C16 C 0.4466(8) 0.2161(8) -0.3984(6) 0.084(3) 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 Re1 0.0561(2) 0.0402(2) 0.0434(2) -0.00357(12) 0.01608(12) -0.00554(13) S2 0.0644(11) 0.0590(10) 0.0430(8) -0.0011(9) 0.0120(8) -0.0032(9) S1 0.0714(12) 0.0541(10) 0.0590(10) 0.0012(9) 0.0295(9) 0.0068(9) N2 0.066(4) 0.040(3) 0.048(3) 0.006(3) 0.020(3) 0.002(3) N1 0.051(3) 0.051(3) 0.051(3) 0.001(3) 0.017(3) 0.000(3) F1 0.127(4) 0.080(3) 0.088(3) -0.014(3) 0.033(3) -0.015(3) F2 0.116(4) 0.101(4) 0.088(4) 0.030(3) 0.035(3) 0.005(3) F3 0.172(7) 0.088(4) 0.125(5) -0.016(4) 0.025(5) -0.015(4) F4 0.133(5) 0.083(3) 0.124(4) 0.039(4) 0.043(4) 0.014(3) O1 0.075(3) 0.047(3) 0.064(3) -0.011(2) 0.027(3) -0.020(2) O2 0.103(4) 0.052(3) 0.082(4) 0.010(3) 0.031(3) 0.028(3) O3 0.089(4) 0.070(3) 0.044(3) -0.008(3) 0.017(3) -0.005(3) O4 0.070(4) 0.128(5) 0.063(3) 0.003(4) 0.022(3) 0.018(4) O5 0.064(4) 0.119(5) 0.066(3) 0.005(4) 0.020(3) 0.011(3) O7 0.150(8) 0.136(7) 0.090(5) -0.008(5) 0.012(5) -0.034(6) C17 0.246(18) 0.125(10) 0.087(8) 0.006(8) 0.076(10) -0.035(10) C18 0.108(8) 0.100(7) 0.095(7) 0.002(6) 0.050(6) -0.018(6) O6 0.137(6) 0.083(4) 0.068(4) 0.001(4) 0.039(4) -0.023(4) C19 0.086(7) 0.098(7) 0.083(6) 0.012(6) 0.032(6) 0.008(6) C20 0.143(10) 0.116(9) 0.107(8) 0.033(7) 0.049(8) 0.002(8) C1 0.077(5) 0.067(4) 0.059(4) -0.009(4) 0.028(4) -0.007(4) C2 0.074(5) 0.068(4) 0.045(4) 0.006(4) 0.023(4) 0.002(4) C3 0.065(5) 0.055(4) 0.055(4) 0.012(4) 0.012(3) -0.001(4) C4 0.060(5) 0.052(4) 0.060(4) 0.008(4) 0.013(4) 0.004(4) C5 0.061(4) 0.047(4) 0.045(3) -0.009(3) 0.018(3) -0.009(3) C6 0.063(4) 0.052(4) 0.045(4) -0.002(3) 0.021(3) -0.012(3) C7 0.071(5) 0.062(4) 0.051(4) 0.012(4) 0.015(4) 0.012(4) C8 0.112(7) 0.039(4) 0.055(4) 0.010(4) 0.018(4) 0.002(4) C9 0.075(5) 0.068(5) 0.059(4) 0.019(4) 0.004(4) -0.014(4) C10 0.068(5) 0.076(5) 0.057(4) 0.010(4) 0.021(4) 0.002(4) C11 0.066(5) 0.092(6) 0.063(5) 0.009(5) 0.029(4) 0.005(4) C12 0.085(6) 0.070(5) 0.078(6) -0.005(5) 0.040(5) -0.004(5) C13 0.095(7) 0.082(6) 0.068(5) 0.015(5) 0.036(5) 0.000(5) C14 0.095(7) 0.086(6) 0.058(5) -0.002(5) 0.021(5) -0.006(5) C15 0.105(7) 0.083(6) 0.080(6) -0.020(6) 0.037(6) -0.017(5) C16 0.087(6) 0.077(6) 0.090(7) 0.017(6) 0.036(5) 0.008(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 Re1 O1 1.683(4) . ? Re1 N1 1.988(5) . ? Re1 N2 2.024(5) . ? Re1 S1 2.285(2) . ? Re1 S2 2.359(2) . ? S2 C3 1.817(7) . ? S2 C2 1.820(7) . ? S1 C1 1.839(7) . ? N2 C6 1.372(8) . ? N2 C7 1.467(8) . ? N1 C4 1.388(8) . ? N1 C5 1.448(7) . ? F1 C12 1.348(9) . ? F2 C13 1.355(9) . ? F3 C15 1.342(10) . ? F4 C16 1.358(9) . ? O2 C4 1.211(8) . ? O3 C6 1.220(7) . ? O4 C10 1.185(9) . ? O5 C10 1.369(9) . ? O5 C11 1.387(10) . ? O7 C19 1.208(12) . ? C17 C18 1.461(14) . ? C18 O6 1.465(10) . ? O6 C19 1.324(11) . ? C19 C20 1.506(13) . ? C1 C2 1.511(10) . ? C3 C4 1.506(9) . ? C5 C6 1.517(9) . ? C7 C8 1.523(9) . ? C8 C9 1.503(10) . ? C9 C10 1.486(10) . ? C11 C12 1.368(11) . ? C11 C16 1.373(12) . ? C12 C13 1.407(12) . ? C13 C14 1.364(11) . ? C14 C15 1.377(12) . ? C15 C16 1.373(13) . ? 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 Re1 N1 118.6(2) . . ? O1 Re1 N2 105.8(2) . . ? N1 Re1 N2 78.5(2) . . ? O1 Re1 S1 114.2(2) . . ? N1 Re1 S1 127.2(2) . . ? N2 Re1 S1 89.1(2) . . ? O1 Re1 S2 102.5(2) . . ? N1 Re1 S2 82.3(2) . . ? N2 Re1 S2 150.86(15) . . ? S1 Re1 S2 85.20(7) . . ? C3 S2 C2 105.6(3) . . ? C3 S2 Re1 101.3(2) . . ? C2 S2 Re1 104.2(2) . . ? C1 S1 Re1 106.2(3) . . ? C6 N2 C7 117.1(6) . . ? C6 N2 Re1 118.3(4) . . ? C7 N2 Re1 124.4(4) . . ? C4 N1 C5 116.3(5) . . ? C4 N1 Re1 125.7(4) . . ? C5 N1 Re1 118.0(4) . . ? C10 O5 C11 115.4(6) . . ? C17 C18 O6 108.2(8) . . ? C19 O6 C18 116.6(8) . . ? O7 C19 O6 123.4(10) . . ? O7 C19 C20 126.2(10) . . ? O6 C19 C20 110.4(10) . . ? C2 C1 S1 109.9(5) . . ? C1 C2 S2 106.7(5) . . ? C4 C3 S2 112.8(5) . . ? O2 C4 N1 123.0(7) . . ? O2 C4 C3 120.8(7) . . ? N1 C4 C3 116.0(6) . . ? N1 C5 C6 109.5(5) . . ? O3 C6 N2 125.3(7) . . ? O3 C6 C5 121.7(6) . . ? N2 C6 C5 113.0(5) . . ? N2 C7 C8 112.5(6) . . ? C9 C8 C7 113.7(6) . . ? C10 C9 C8 113.3(7) . . ? O4 C10 O5 121.6(7) . . ? O4 C10 C9 126.8(8) . . ? O5 C10 C9 111.5(7) . . ? C12 C11 C16 118.7(8) . . ? C12 C11 O5 119.8(8) . . ? C16 C11 O5 121.3(8) . . ? F1 C12 C11 121.4(8) . . ? F1 C12 C13 118.8(8) . . ? C11 C12 C13 119.8(8) . . ? F2 C13 C14 120.2(8) . . ? F2 C13 C12 118.0(8) . . ? C14 C13 C12 121.7(8) . . ? C13 C14 C15 117.2(8) . . ? F3 C15 C16 118.1(9) . . ? F3 C15 C14 120.1(9) . . ? C16 C15 C14 121.8(8) . . ? F4 C16 C11 119.3(9) . . ? F4 C16 C15 119.8(9) . . ? C11 C16 C15 120.8(8) . . ? _refine_diff_density_max 1.730 _refine_diff_density_min -1.170 _refine_diff_density_rms 0.131