# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/2107 data_global _publ_contact_author_name 'Gatteschi,D.' _publ_contact_author_address ; Dipartimento di Chimica, Universita' di Firenze, Via Maragliano 75-77, 50144 Firenze, Italy ; _publ_contact_author_email 'gattesch@blu.chim1.unifi.it' _publ_contact_author_fax +39-055-354845 _publ_requested_journal 'Journal of Chemical Society, Dalton Ttransactions' _publ_section_title ; Supramolecular interactions and magnetism of metal-radical chains ; _publ_author_name ; Caneschi,A. Gatteschi,D. Lalioti,N. Sangregorio,C. Sessoli,R. ; _publ_author_address ; Dipartimento di Chimica, Universita' di Firenze, Via Maragliano 75-77, 50144 Firenze, Italy ; _publ_section_abstract ? data_1 _audit_creation_method SHELXL93 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H21 Co F12 N2 O7' _chemical_formula_weight 736.36 _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' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Co' 'Co' .3494 .9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M P32 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' _cell_length_a 11.295(3) _cell_length_b 11.294(2) _cell_length_c 20.570(6) _cell_angle_alpha 90.08(2) _cell_angle_beta 89.93(2) _cell_angle_gamma 120.030(10) _cell_volume 2271.8(10) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.35 _cell_measurement_theta_max 12.33 _exptl_crystal_description 'needle with an hexagonal base' _exptl_crystal_colour blue-green _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid ? _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method ? _exptl_crystal_F_000 1110 _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 'none' _exptl_absorpt_correction_T_max 'none' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'enraf nonius cad4 diffractometer' _diffrn_measurement_method omega-2theta _diffrn_standards_number 38 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3413 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.98 _reflns_number_total 3413 _reflns_number_observed 2616 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR92 (Giacovazzo, 1992)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+( 0.0825P)^2^+0.4777P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 3412 _refine_ls_number_parameters 420 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_obs 0.0433 _refine_ls_wR_factor_all 0.1345 _refine_ls_wR_factor_obs 0.1179 _refine_ls_goodness_of_fit_all 1.043 _refine_ls_goodness_of_fit_obs 1.066 _refine_ls_restrained_S_all 1.045 _refine_ls_restrained_S_obs 1.066 _refine_ls_shift/esd_max 0.019 _refine_ls_shift/esd_mean 0.002 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 Co1 Co 0.59545(8) 0.47955(7) -0.20932(3) 0.0461(2) Uani 1 d . . O2 O 0.7407(4) 0.3286(5) -0.4661(2) 0.0532(10) Uani 1 d . . O3 O 0.7672(4) 0.5063(4) -0.2611(2) 0.0490(9) Uani 1 d . . O4 O 0.4386(5) 0.4501(5) -0.1482(2) 0.0587(11) Uani 1 d . . O5 O 0.4725(5) 0.2926(5) -0.2504(2) 0.0604(11) Uani 1 d . . O6 O 0.7137(5) 0.6817(4) -0.1891(2) 0.0604(11) Uani 1 d . . O7 O 0.5065(5) 0.5406(5) -0.2808(2) 0.0635(12) Uani 1 d . . N8 N 0.7700(5) 0.4303(5) -0.3079(2) 0.0469(11) Uani 1 d . . N9 N 0.7594(5) 0.3489(5) -0.4044(2) 0.0467(10) Uani 1 d . . C10 C 0.6245(16) 0.8761(15) -0.5211(7) 0.145(5) Uani 1 d . . H10A H 0.6237(96) 0.9602(43) -0.5262(39) 0.217 Uiso 1 calc R . H10B H 0.5337(28) 0.8035(82) -0.5115(27) 0.217 Uiso 1 calc R . H10C H 0.6559(70) 0.8555(120) -0.5606(13) 0.217 Uiso 1 calc R . C11 C 0.7161(9) 0.7761(9) -0.4477(4) 0.074(2) Uani 1 d . . C12 C 0.6356(9) 0.6480(10) -0.4717(4) 0.077(2) Uani 1 d . . H12 H 0.5726(9) 0.6331(10) -0.5042(4) 0.092 Uiso 1 calc R . C13 C 0.6474(8) 0.5373(8) -0.4473(3) 0.061(2) Uani 1 d . . H13 H 0.5945(8) 0.4502(8) -0.4647(3) 0.073 Uiso 1 calc R . C14 C 0.7384(6) 0.5597(6) -0.3975(3) 0.0477(12) Uani 1 d . . C15 C 0.8160(7) 0.6905(7) -0.3728(3) 0.0572(15) Uani 1 d . . H15 H 0.8747(7) 0.7057(7) -0.3381(3) 0.069 Uiso 1 calc R . C16 C 0.8080(10) 0.7993(8) -0.3987(4) 0.079(2) Uani 1 d . . H16 H 0.8643(10) 0.8874(8) -0.3830(4) 0.094 Uiso 1 calc R . C17 C 0.7524(7) 0.4480(7) -0.3721(3) 0.0454(11) Uani 1 d . . C18 C 0.7607(9) 0.2431(7) -0.3601(3) 0.068(2) Uani 1 d . . C19 C 0.8523(13) 0.1934(10) -0.3876(4) 0.099(4) Uani 1 d . . H19A H 0.8678(74) 0.1417(76) -0.3551(14) 0.149 Uiso 1 calc R . H19B H 0.9382(33) 0.2705(10) -0.4003(38) 0.149 Uiso 1 calc R . H19C H 0.8092(39) 0.1365(70) -0.4248(25) 0.149 Uiso 1 calc R . C20 C 0.6095(14) 0.1290(8) -0.3566(5) 0.124(5) Uani 1 d . . H20A H 0.5583(27) 0.1610(39) -0.3324(46) 0.186 Uiso 1 calc R . H20B H 0.6030(18) 0.0502(40) -0.3355(48) 0.186 Uiso 1 calc R . H20C H 0.5730(34) 0.1048(80) -0.3998(5) 0.186 Uiso 1 calc R . C21 C 0.8122(11) 0.3258(9) -0.2975(3) 0.075(2) Uani 1 d . . C22 C 0.9711(12) 0.4109(13) -0.2948(5) 0.102(3) Uani 1 d . . H22A H 1.0067(12) 0.3515(19) -0.2853(41) 0.153 Uiso 1 calc R . H22B H 0.9988(12) 0.4791(58) -0.2614(29) 0.153 Uiso 1 calc R . H22C H 1.0058(13) 0.4546(71) -0.3360(14) 0.153 Uiso 1 calc R . C23 C 0.7518(15) 0.2475(11) -0.2355(4) 0.117(5) Uani 1 d . . H23A H 0.8011(65) 0.3033(39) -0.1990(4) 0.176 Uiso 1 calc R . H23B H 0.7583(94) 0.1659(53) -0.2357(22) 0.176 Uiso 1 calc R . H23C H 0.6575(31) 0.2232(88) -0.2325(23) 0.176 Uiso 1 calc R . C24 C 0.3150(8) 0.3636(8) -0.1599(3) 0.064(2) Uani 1 d . . C25 C 0.2112(10) 0.3758(11) -0.1163(5) 0.091(3) Uani 1 d . . C26 C 0.2633(8) 0.2619(9) -0.2074(4) 0.072(2) Uani 1 d . . H26 H 0.1689(8) 0.2078(9) -0.2113(4) 0.086 Uiso 1 calc R . C27 C 0.3432(8) 0.2378(7) -0.2482(3) 0.067(2) Uani 1 d . . C28 C 0.2725(11) 0.1276(12) -0.3014(5) 0.101(3) Uani 1 d . . C29 C 0.5074(8) 0.6520(9) -0.2819(3) 0.069(2) Uani 1 d . . C30 C 0.3992(12) 0.6554(13) -0.3241(6) 0.098(3) Uani 1 d . . C31 C 0.5977(11) 0.7701(9) -0.2472(5) 0.095(3) Uani 1 d . . H31 H 0.5904(11) 0.8481(9) -0.2523(5) 0.114 Uiso 1 calc R . C32 C 0.6950(10) 0.7762(8) -0.2066(4) 0.076(2) Uani 1 d . . C33 C 0.7998(19) 0.9187(10) -0.1753(10) 0.162(7) Uani 1 d . . O8 O 0.7136(10) 0.8896(7) -0.4692(4) 0.120(3) Uani 1 d . . F251 F 0.2517(7) 0.3995(9) -0.0554(3) 0.127(2) Uani 1 d . . F252 F 0.0914(7) 0.2713(10) -0.1168(5) 0.176(4) Uani 1 d . . F253 F 0.2022(11) 0.4826(12) -0.1346(4) 0.174(4) Uani 1 d . . F281 F 0.3035(9) 0.0294(7) -0.2957(3) 0.135(3) Uani 1 d . . F282 F 0.3157(11) 0.1756(9) -0.3588(3) 0.162(4) Uani 1 d . . F283 F 0.1430(9) 0.0680(12) -0.3011(5) 0.218(6) Uani 1 d . . F301 F 0.4526(10) 0.7679(11) -0.3607(5) 0.196(5) Uani 1 d . . F302 F 0.3545(10) 0.5660(11) -0.3694(5) 0.175(4) Uani 1 d . . F303 F 0.3049(11) 0.6471(19) -0.2947(5) 0.259(9) Uani 1 d . . F331 F 0.8625(11) 1.0050(9) -0.2236(6) 0.186(4) Uani 1 d . . F332 F 0.7269(13) 0.9813(9) -0.1554(5) 0.185(4) Uani 1 d . . F333 F 0.8695(15) 0.9185(8) -0.1353(7) 0.291(10) 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 Co1 0.0601(5) 0.0453(4) 0.0341(3) -0.0024(3) -0.0015(3) 0.0273(4) O2 0.061(3) 0.069(3) 0.032(2) -0.009(2) 0.004(2) 0.034(2) O3 0.063(2) 0.053(2) 0.031(2) -0.005(2) 0.005(2) 0.029(2) O4 0.059(3) 0.066(3) 0.052(2) -0.006(2) 0.001(2) 0.032(2) O5 0.071(3) 0.054(3) 0.053(2) -0.011(2) -0.007(2) 0.029(2) O6 0.085(3) 0.048(2) 0.053(2) -0.003(2) -0.011(2) 0.036(2) O7 0.069(3) 0.072(3) 0.049(2) 0.003(2) -0.007(2) 0.035(3) N8 0.070(3) 0.048(2) 0.029(2) 0.003(2) 0.007(2) 0.035(2) N9 0.063(3) 0.046(3) 0.034(2) -0.001(2) 0.006(2) 0.030(2) C10 0.194(14) 0.149(11) 0.141(11) 0.042(9) -0.029(10) 0.124(11) C11 0.100(6) 0.079(5) 0.068(4) 0.003(4) -0.001(4) 0.064(5) C12 0.097(6) 0.102(6) 0.058(4) 0.003(4) -0.014(4) 0.069(5) C13 0.077(4) 0.072(4) 0.047(3) -0.011(3) -0.011(3) 0.047(4) C14 0.061(3) 0.052(3) 0.036(2) 0.006(2) 0.005(2) 0.033(3) C15 0.072(4) 0.053(3) 0.050(3) 0.006(3) -0.004(3) 0.034(3) C16 0.107(6) 0.051(4) 0.077(5) -0.004(3) -0.013(4) 0.038(4) C17 0.058(3) 0.049(3) 0.030(2) 0.000(2) 0.005(2) 0.028(2) C18 0.112(6) 0.062(4) 0.047(3) 0.014(3) 0.025(4) 0.056(4) C19 0.194(11) 0.107(7) 0.060(4) 0.019(4) 0.036(6) 0.123(8) C20 0.186(12) 0.046(4) 0.092(7) 0.002(4) 0.050(7) 0.022(6) C21 0.134(7) 0.088(5) 0.040(3) 0.016(3) 0.017(4) 0.083(6) C22 0.123(8) 0.158(10) 0.080(5) -0.016(6) -0.019(6) 0.112(8) C23 0.245(14) 0.126(8) 0.051(4) 0.034(5) 0.048(6) 0.145(10) C24 0.073(5) 0.068(4) 0.055(3) -0.002(3) 0.002(3) 0.040(4) C25 0.072(6) 0.100(7) 0.106(7) -0.007(6) 0.010(5) 0.047(5) C26 0.058(4) 0.075(5) 0.076(4) -0.011(4) -0.009(3) 0.029(3) C27 0.078(5) 0.064(4) 0.056(4) -0.012(3) -0.012(3) 0.033(4) C28 0.088(7) 0.093(7) 0.094(7) -0.046(6) -0.029(5) 0.025(6) C29 0.065(4) 0.094(6) 0.060(4) 0.019(4) 0.002(3) 0.049(4) C30 0.108(8) 0.117(8) 0.097(7) 0.010(6) -0.017(6) 0.077(7) C31 0.116(7) 0.064(5) 0.122(7) -0.005(5) -0.032(6) 0.056(5) C32 0.100(6) 0.052(4) 0.085(5) -0.006(3) -0.022(4) 0.045(4) C33 0.200(15) 0.043(5) 0.246(18) 0.005(8) -0.085(14) 0.062(8) O8 0.175(8) 0.099(5) 0.124(5) 0.024(4) -0.022(5) 0.097(5) F251 0.131(5) 0.188(7) 0.081(4) -0.017(4) 0.022(3) 0.095(5) F252 0.073(4) 0.192(8) 0.207(8) -0.079(7) 0.039(4) 0.023(5) F253 0.225(10) 0.229(10) 0.170(8) 0.039(7) 0.065(7) 0.191(9) F281 0.165(7) 0.082(4) 0.117(5) -0.049(4) -0.022(4) 0.031(4) F282 0.251(10) 0.157(7) 0.071(4) -0.042(4) -0.065(5) 0.097(7) F283 0.102(6) 0.253(12) 0.243(11) -0.179(10) -0.061(6) 0.048(6) F301 0.162(7) 0.184(9) 0.229(10) 0.074(8) -0.077(7) 0.077(6) F302 0.181(8) 0.214(10) 0.171(8) -0.043(7) -0.107(7) 0.129(8) F303 0.163(8) 0.570(28) 0.153(8) 0.033(11) 0.002(6) 0.266(15) F331 0.177(8) 0.086(5) 0.242(12) -0.015(6) -0.018(8) 0.026(5) F332 0.280(13) 0.111(6) 0.167(8) -0.041(5) -0.009(8) 0.100(7) F333 0.383(18) 0.081(5) 0.396(17) -0.085(8) -0.309(16) 0.106(8) _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 Co1 O6 2.028(4) . ? Co1 O5 2.040(4) . ? Co1 O4 2.057(5) . ? Co1 O7 2.085(5) . ? Co1 O3 2.097(4) . ? Co1 O2 2.111(4) 2_655 ? O2 N9 1.287(6) . ? O2 Co1 2.108(4) 3_664 ? O3 N8 1.300(6) . ? O4 C24 1.264(9) . ? O5 C27 1.270(9) . ? O6 C32 1.241(9) . ? O7 C29 1.253(10) . ? N8 C17 1.366(7) . ? N8 C21 1.493(9) . ? N9 C17 1.337(8) . ? N9 C18 1.510(8) . ? C10 O8 1.423(14) . ? C11 C12 1.358(12) . ? C11 O8 1.371(9) . ? C11 C16 1.375(12) . ? C12 C13 1.414(11) . ? C13 C14 1.383(9) . ? C14 C15 1.382(9) . ? C14 C17 1.446(9) . ? C15 C16 1.383(10) . ? C18 C19 1.511(10) . ? C18 C21 1.525(10) . ? C18 C20 1.543(15) . ? C21 C23 1.506(10) . ? C21 C22 1.56(2) . ? C24 C26 1.393(10) . ? C24 C25 1.535(12) . ? C25 F252 1.274(12) . ? C25 F251 1.315(12) . ? C25 F253 1.315(13) . ? C26 C27 1.356(11) . ? C27 C28 1.545(11) . ? C28 F283 1.267(14) . ? C28 F282 1.289(14) . ? C28 F281 1.325(14) . ? C29 C31 1.402(12) . ? C29 C30 1.516(11) . ? C30 F303 1.187(13) . ? C30 F302 1.276(13) . ? C30 F301 1.333(13) . ? C31 C32 1.356(12) . ? C32 C33 1.580(15) . ? C33 F333 1.14(2) . ? C33 F331 1.32(2) . ? C33 F332 1.39(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 O6 Co1 O5 166.6(2) . . ? O6 Co1 O4 95.0(2) . . ? O5 Co1 O4 90.0(2) . . ? O6 Co1 O7 85.8(2) . . ? O5 Co1 O7 81.9(2) . . ? O4 Co1 O7 88.1(2) . . ? O6 Co1 O3 84.3(2) . . ? O5 Co1 O3 92.4(2) . . ? O4 Co1 O3 172.7(2) . . ? O7 Co1 O3 99.1(2) . . ? O6 Co1 O2 95.5(2) . 2_655 ? O5 Co1 O2 97.2(2) . 2_655 ? O4 Co1 O2 87.6(2) . 2_655 ? O7 Co1 O2 175.6(2) . 2_655 ? O3 Co1 O2 85.2(2) . 2_655 ? N9 O2 Co1 129.7(4) . 3_664 ? N8 O3 Co1 127.3(4) . . ? C24 O4 Co1 122.5(4) . . ? C27 O5 Co1 120.8(4) . . ? C32 O6 Co1 127.5(5) . . ? C29 O7 Co1 125.6(5) . . ? O3 N8 C17 124.5(5) . . ? O3 N8 C21 122.5(5) . . ? C17 N8 C21 112.6(5) . . ? O2 N9 C17 124.4(5) . . ? O2 N9 C18 121.4(5) . . ? C17 N9 C18 113.0(4) . . ? C12 C11 O8 124.2(8) . . ? C12 C11 C16 120.5(7) . . ? O8 C11 C16 115.2(8) . . ? C11 C12 C13 120.2(7) . . ? C14 C13 C12 119.5(7) . . ? C15 C14 C13 118.9(6) . . ? C15 C14 C17 120.8(5) . . ? C13 C14 C17 120.3(6) . . ? C14 C15 C16 121.3(6) . . ? C11 C16 C15 119.5(7) . . ? N9 C17 N8 106.5(5) . . ? N9 C17 C14 129.0(5) . . ? N8 C17 C14 124.4(5) . . ? N9 C18 C19 110.4(5) . . ? N9 C18 C21 100.2(5) . . ? C19 C18 C21 114.9(8) . . ? N9 C18 C20 104.1(7) . . ? C19 C18 C20 112.6(8) . . ? C21 C18 C20 113.3(7) . . ? N8 C21 C23 111.0(6) . . ? N8 C21 C18 100.8(5) . . ? C23 C21 C18 115.7(8) . . ? N8 C21 C22 104.0(7) . . ? C23 C21 C22 112.0(9) . . ? C18 C21 C22 112.1(7) . . ? O4 C24 C26 128.0(7) . . ? O4 C24 C25 114.7(7) . . ? C26 C24 C25 117.3(8) . . ? F252 C25 F251 107.2(10) . . ? F252 C25 F253 108.3(11) . . ? F251 C25 F253 105.4(9) . . ? F252 C25 C24 114.7(9) . . ? F251 C25 C24 111.8(8) . . ? F253 C25 C24 109.1(9) . . ? C27 C26 C24 123.5(7) . . ? O5 C27 C26 129.9(7) . . ? O5 C27 C28 111.9(7) . . ? C26 C27 C28 118.1(8) . . ? F283 C28 F282 108.7(11) . . ? F283 C28 F281 105.8(11) . . ? F282 C28 F281 103.4(10) . . ? F283 C28 C27 114.8(9) . . ? F282 C28 C27 112.0(9) . . ? F281 C28 C27 111.3(9) . . ? O7 C29 C31 125.6(7) . . ? O7 C29 C30 115.8(8) . . ? C31 C29 C30 118.6(8) . . ? F303 C30 F302 108.9(13) . . ? F303 C30 F301 108.8(11) . . ? F302 C30 F301 98.8(10) . . ? F303 C30 C29 114.2(10) . . ? F302 C30 C29 113.8(9) . . ? F301 C30 C29 111.3(9) . . ? C32 C31 C29 123.1(7) . . ? O6 C32 C31 128.2(8) . . ? O6 C32 C33 113.3(8) . . ? C31 C32 C33 118.5(8) . . ? F333 C33 F331 115.4(18) . . ? F333 C33 F332 112.0(19) . . ? F331 C33 F332 94.7(8) . . ? F333 C33 C32 117.2(9) . . ? F331 C33 C32 107.3(14) . . ? F332 C33 C32 107.7(13) . . ? C11 O8 C10 119.2(9) . . ? _refine_diff_density_max .264 _refine_diff_density_min -.297 _refine_diff_density_rms .057 data_2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H21 Co F12 N2 O6' _chemical_formula_weight 720.36 _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' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Co' 'Co' .3494 .9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M P31 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 11.2490(10) _cell_length_b 11.254(4) _cell_length_c 20.307(6) _cell_angle_alpha 90.03(3) _cell_angle_beta 90.03(2) _cell_angle_gamma 119.95(2) _cell_volume 2227.5(10) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.45 _cell_measurement_theta_max 12.21 _exptl_crystal_description 'needle with an hexagonal base ' _exptl_crystal_colour blue-green _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid ? _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method ? _exptl_crystal_F_000 1086 _exptl_absorpt_coefficient_mu 0.694 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 'none' _exptl_absorpt_correction_T_max 'none' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'enraf nonius cad4 diffractometer' _diffrn_measurement_method omega-2theta _diffrn_standards_number 40 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3714 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3711 _reflns_number_observed 3179 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR92 (Giacovazzo, 1992)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 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^)+( 0.0931P)^2^+0.6986P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 3706 _refine_ls_number_parameters 411 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_obs 0.0515 _refine_ls_wR_factor_all 0.1556 _refine_ls_wR_factor_obs 0.1349 _refine_ls_goodness_of_fit_all 1.067 _refine_ls_goodness_of_fit_obs 1.047 _refine_ls_restrained_S_all 1.108 _refine_ls_restrained_S_obs 1.047 _refine_ls_shift/esd_max 0.404 _refine_ls_shift/esd_mean 0.073 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 Co1 Co 0.43852(7) 0.26286(8) 0.46806(3) 0.0396(2) Uani 1 d . . O5 O 0.5749(4) 0.4389(4) 0.5213(2) 0.0435(9) Uani 1 d . . O1 O 0.5105(5) 0.1496(5) 0.5120(2) 0.0513(10) Uani 1 d . . O4 O 0.3527(4) 0.3796(5) 0.4462(2) 0.0484(10) Uani 1 d . . O6 O 0.7569(4) 0.4199(4) 0.7222(2) 0.0455(9) Uani 1 d . . O2 O 0.3161(5) 0.0988(5) 0.4078(2) 0.0522(11) Uani 1 d . . N1 N 0.6612(5) 0.4487(5) 0.5658(2) 0.0407(10) Uani 1 d . . N2 N 0.7474(5) 0.4412(5) 0.6602(2) 0.0394(9) Uani 1 d . . O3 O 0.2850(5) 0.1700(5) 0.5404(2) 0.0560(11) Uani 1 d . . C1 C 0.4425(8) 0.0199(8) 0.5125(3) 0.056(2) Uani 1 d . . C2 C 0.3377(8) -0.0664(7) 0.4720(3) 0.058(2) Uani 1 d . . H2 H 0.3009(8) -0.1603(7) 0.4775(3) 0.070 Uiso 1 calc R . C3 C 0.2830(7) -0.0221(7) 0.4231(3) 0.0534(14) Uani 1 d . . C4 C 0.4907(12) -0.0419(10) 0.5678(4) 0.079(2) Uani 1 d . . C5 C 0.1670(9) -0.1311(8) 0.3819(5) 0.073(2) Uani 1 d . . C6 C 0.1812(7) 0.1794(7) 0.5439(3) 0.056(2) Uani 1 d . . C7 C 0.1571(8) 0.2738(10) 0.5120(5) 0.078(2) Uani 1 d . . H7 H 0.0765(8) 0.2742(10) 0.5217(5) 0.094 Uiso 1 calc R . C8 C 0.2451(7) 0.3672(8) 0.4668(3) 0.057(2) Uani 1 d . . C9 C 0.0654(10) 0.0741(9) 0.5881(5) 0.083(3) Uani 1 d . . C10 C 0.2092(13) 0.4723(15) 0.4395(7) 0.113(5) Uani 1 d . . C11 C 0.8100(7) 0.5105(9) 0.5506(3) 0.056(2) Uani 1 d . . C12 C 0.8553(7) 0.4592(8) 0.6117(3) 0.055(2) Uani 1 d . . C13 C 0.6341(6) 0.4251(6) 0.6317(3) 0.0386(10) Uani 1 d . . C14 C 0.8694(9) 0.6645(9) 0.5512(4) 0.079(2) Uani 1 d . . H14A H 0.9649(20) 0.7089(10) 0.5399(35) 0.119 Uiso 1 calc R . H14B H 0.8593(67) 0.6931(13) 0.5944(11) 0.119 Uiso 1 calc R . H14C H 0.8215(50) 0.6890(12) 0.5198(26) 0.119 Uiso 1 calc R . C15 C 0.8315(10) 0.4627(13) 0.4857(4) 0.091(3) Uani 1 d . . H15A H 0.9277(12) 0.4974(79) 0.4789(20) 0.136 Uiso 1 calc R . H15B H 0.7967(84) 0.4955(77) 0.4513(5) 0.136 Uiso 1 calc R . H15C H 0.7839(77) 0.3642(13) 0.4849(16) 0.136 Uiso 1 calc R . C16 C 0.8337(11) 0.3134(11) 0.6008(5) 0.086(3) Uani 1 d . . H16A H 0.9054(47) 0.3188(14) 0.5732(33) 0.129 Uiso 1 calc R . H16B H 0.7465(38) 0.2567(25) 0.5801(36) 0.129 Uiso 1 calc R . H16C H 0.8358(83) 0.2743(34) 0.6425(6) 0.129 Uiso 1 calc R . C17 C 0.9965(7) 0.5556(12) 0.6376(4) 0.086(3) Uani 1 d . . H17A H 1.0632(9) 0.5706(66) 0.6044(14) 0.129 Uiso 1 calc R . H17B H 1.0135(31) 0.5163(36) 0.6759(23) 0.129 Uiso 1 calc R . H17C H 1.0030(26) 0.6413(29) 0.6492(36) 0.129 Uiso 1 calc R . C18 C 0.5053(6) 0.3953(6) 0.6621(3) 0.0421(12) Uani 1 d . . C19 C 0.4424(7) 0.4684(8) 0.6460(3) 0.0548(15) Uani 1 d . . H19 H 0.4805(7) 0.5351(8) 0.6134(3) 0.066 Uiso 1 calc R . C20 C 0.3232(9) 0.4457(10) 0.6770(4) 0.074(2) Uani 1 d . . H20 H 0.2830(9) 0.4979(10) 0.6661(4) 0.089 Uiso 1 calc R . C21 C 0.2648(8) 0.3447(12) 0.7243(4) 0.081(3) Uani 1 d . . C22 C 0.3251(8) 0.2684(11) 0.7389(4) 0.082(3) Uani 1 d . . H22 H 0.2842(8) 0.1990(11) 0.7701(4) 0.098 Uiso 1 calc R . C23 C 0.4448(7) 0.2907(9) 0.7088(3) 0.058(2) Uani 1 d . . H23 H 0.4840(7) 0.2374(9) 0.7194(3) 0.070 Uiso 1 calc R . C24 C 0.1339(10) 0.3171(15) 0.7601(6) 0.109(4) Uani 1 d . . H24A H 0.0561(15) 0.2412(68) 0.7397(33) 0.164 Uiso 1 calc R . H24B H 0.1244(55) 0.3971(38) 0.7578(43) 0.164 Uiso 1 calc R . H24C H 0.1392(48) 0.2957(106) 0.8054(14) 0.164 Uiso 1 calc R . F1 F 0.4943(9) 0.0114(8) 0.6241(3) 0.123(2) Uani 1 d . . F2 F 0.6186(8) -0.0134(9) 0.5571(3) 0.121(2) Uani 1 d . . F3 F 0.4187(11) -0.1721(8) 0.5713(5) 0.184(5) Uani 1 d . . F4 F 0.1530(10) -0.2515(6) 0.3855(4) 0.157(4) Uani 1 d . . F5 F 0.1831(8) -0.0986(7) 0.3187(3) 0.121(2) Uani 1 d . . F6 F 0.0504(6) -0.1403(10) 0.3981(4) 0.141(3) Uani 1 d . . F7 F 0.1059(9) 0.0153(9) 0.6282(4) 0.146(3) Uani 1 d . . F8 F 0.0101(9) 0.1307(8) 0.6236(4) 0.151(4) Uani 1 d . . F9 F -0.0255(10) -0.0212(8) 0.5527(4) 0.168(4) Uani 1 d . . F10 F 0.1955(17) 0.5429(13) 0.4856(6) 0.204(6) Uani 1 d . . F11 F 0.2778(11) 0.5420(11) 0.3948(6) 0.198(6) Uani 1 d . . F12 F 0.0804(11) 0.4138(13) 0.4203(6) 0.183(5) 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 Co1 0.0475(4) 0.0506(4) 0.0288(3) 0.0024(3) -0.0007(3) 0.0308(4) O5 0.054(2) 0.055(2) 0.026(2) -0.007(2) -0.010(2) 0.031(2) O1 0.061(3) 0.061(3) 0.043(2) 0.006(2) -0.004(2) 0.039(2) O4 0.048(2) 0.064(3) 0.044(2) 0.009(2) 0.007(2) 0.036(2) O6 0.055(2) 0.052(2) 0.026(2) -0.003(2) -0.008(2) 0.024(2) O2 0.061(3) 0.049(2) 0.043(2) 0.002(2) -0.009(2) 0.025(2) N1 0.050(3) 0.056(3) 0.023(2) -0.005(2) -0.004(2) 0.031(2) N2 0.045(2) 0.050(3) 0.025(2) -0.005(2) -0.004(2) 0.025(2) O3 0.065(3) 0.060(3) 0.042(2) 0.013(2) 0.017(2) 0.031(2) C1 0.068(4) 0.073(4) 0.041(3) 0.014(3) 0.003(3) 0.046(4) C2 0.077(5) 0.048(3) 0.053(4) 0.009(3) -0.008(3) 0.033(3) C3 0.055(4) 0.055(4) 0.045(3) 0.006(3) 0.004(3) 0.024(3) C4 0.120(8) 0.080(6) 0.061(5) 0.014(4) -0.012(5) 0.068(6) C5 0.070(5) 0.053(4) 0.078(5) -0.001(4) -0.018(4) 0.016(4) C6 0.051(3) 0.056(4) 0.048(3) 0.000(3) 0.014(3) 0.019(3) C7 0.059(4) 0.090(6) 0.097(6) 0.024(5) 0.028(4) 0.046(4) C8 0.054(4) 0.072(4) 0.059(4) 0.006(3) 0.007(3) 0.042(4) C9 0.070(5) 0.068(5) 0.089(6) 0.017(5) 0.026(5) 0.018(4) C10 0.116(8) 0.157(11) 0.133(9) 0.065(8) 0.065(8) 0.119(9) C11 0.051(3) 0.084(5) 0.031(3) -0.010(3) -0.002(2) 0.032(3) C12 0.054(4) 0.088(5) 0.033(3) -0.013(3) -0.006(2) 0.044(4) C13 0.047(3) 0.049(3) 0.023(2) -0.003(2) -0.003(2) 0.026(2) C14 0.069(5) 0.083(6) 0.066(5) 0.016(4) 0.009(4) 0.024(4) C15 0.074(5) 0.167(10) 0.037(3) -0.022(5) 0.000(3) 0.064(6) C16 0.099(7) 0.105(7) 0.089(6) -0.018(5) -0.005(5) 0.077(6) C17 0.037(3) 0.151(9) 0.053(4) -0.021(5) -0.004(3) 0.034(4) C18 0.039(3) 0.050(3) 0.033(3) -0.006(2) -0.002(2) 0.019(2) C19 0.052(3) 0.071(4) 0.047(3) 0.000(3) 0.003(3) 0.035(3) C20 0.068(5) 0.107(6) 0.066(5) -0.015(4) 0.000(4) 0.058(5) C21 0.048(4) 0.133(8) 0.059(5) -0.010(5) 0.004(3) 0.042(5) C22 0.055(4) 0.115(7) 0.055(4) 0.021(4) 0.011(3) 0.028(5) C23 0.048(3) 0.079(5) 0.041(3) 0.015(3) 0.004(3) 0.027(3) C24 0.067(5) 0.174(12) 0.090(7) -0.007(7) 0.008(5) 0.063(7) F1 0.193(7) 0.161(6) 0.045(3) 0.027(3) -0.003(3) 0.110(6) F2 0.153(6) 0.180(7) 0.095(4) 0.029(4) -0.012(4) 0.132(6) F3 0.214(9) 0.087(4) 0.196(9) 0.063(5) -0.099(8) 0.034(5) F4 0.211(9) 0.060(3) 0.179(8) -0.033(4) -0.116(7) 0.052(4) F5 0.139(6) 0.104(4) 0.065(3) -0.015(3) -0.031(3) 0.020(4) F6 0.065(4) 0.184(8) 0.136(6) -0.037(5) -0.026(4) 0.033(4) F7 0.137(6) 0.148(7) 0.143(6) 0.093(6) 0.054(5) 0.064(5) F8 0.152(7) 0.136(6) 0.153(7) 0.038(5) 0.109(6) 0.064(6) F9 0.138(6) 0.102(5) 0.127(6) 0.012(5) 0.006(5) -0.043(5) F10 0.334(17) 0.202(10) 0.196(10) 0.008(9) 0.016(10) 0.225(12) F11 0.219(10) 0.237(11) 0.249(11) 0.177(10) 0.137(9) 0.197(10) F12 0.162(8) 0.230(12) 0.220(11) 0.047(9) -0.027(8) 0.146(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 Co1 O1 2.027(4) . ? Co1 O4 2.030(4) . ? Co1 O2 2.064(4) . ? Co1 O5 2.100(4) . ? Co1 O3 2.105(4) . ? Co1 O6 2.120(4) 2_654 ? O5 N1 1.290(6) . ? O1 C1 1.265(9) . ? O4 C8 1.220(8) . ? O6 N2 1.295(6) . ? O6 Co1 2.119(4) 3_665 ? O2 C3 1.258(8) . ? N1 C13 1.369(7) . ? N1 C11 1.490(8) . ? N2 C13 1.327(8) . ? N2 C12 1.497(8) . ? O3 C6 1.226(9) . ? C1 C2 1.365(10) . ? C1 C4 1.555(9) . ? C2 C3 1.385(9) . ? C3 C5 1.520(10) . ? C4 F3 1.274(12) . ? C4 F1 1.283(11) . ? C4 F2 1.327(13) . ? C5 F4 1.286(10) . ? C5 F6 1.305(12) . ? C5 F5 1.323(10) . ? C6 C7 1.382(12) . ? C6 C9 1.538(10) . ? C7 C8 1.375(10) . ? C8 C10 1.533(11) . ? C9 F9 1.271(12) . ? C9 F7 1.269(12) . ? C9 F8 1.307(12) . ? C10 F11 1.197(12) . ? C10 F10 1.29(2) . ? C10 F12 1.31(2) . ? C11 C15 1.489(9) . ? C11 C14 1.514(13) . ? C11 C12 1.558(10) . ? C12 C17 1.502(10) . ? C12 C16 1.550(12) . ? C13 C18 1.453(8) . ? C18 C19 1.367(9) . ? C18 C23 1.395(9) . ? C19 C20 1.385(10) . ? C20 C21 1.379(14) . ? C21 C22 1.365(14) . ? C21 C24 1.529(12) . ? C22 C23 1.383(11) . ? 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 Co1 O4 166.3(2) . . ? O1 Co1 O2 89.8(2) . . ? O4 Co1 O2 97.4(2) . . ? O1 Co1 O5 91.9(2) . . ? O4 Co1 O5 82.0(2) . . ? O2 Co1 O5 174.4(2) . . ? O1 Co1 O3 82.3(2) . . ? O4 Co1 O3 86.4(2) . . ? O2 Co1 O3 87.3(2) . . ? O5 Co1 O3 98.1(2) . . ? O1 Co1 O6 97.1(2) . 2_654 ? O4 Co1 O6 94.9(2) . 2_654 ? O2 Co1 O6 86.4(2) . 2_654 ? O5 Co1 O6 88.1(2) . 2_654 ? O3 Co1 O6 173.7(2) . 2_654 ? N1 O5 Co1 127.2(3) . . ? C1 O1 Co1 121.8(4) . . ? C8 O4 Co1 128.0(4) . . ? N2 O6 Co1 129.0(3) . 3_665 ? C3 O2 Co1 121.7(4) . . ? O5 N1 C13 125.6(5) . . ? O5 N1 C11 121.1(4) . . ? C13 N1 C11 112.6(5) . . ? O6 N2 C13 124.1(5) . . ? O6 N2 C12 121.9(4) . . ? C13 N2 C12 112.9(4) . . ? C6 O3 Co1 125.4(4) . . ? O1 C1 C2 128.7(6) . . ? O1 C1 C4 112.1(6) . . ? C2 C1 C4 119.2(7) . . ? C1 C2 C3 123.8(6) . . ? O2 C3 C2 128.5(6) . . ? O2 C3 C5 114.1(6) . . ? C2 C3 C5 117.4(6) . . ? F3 C4 F1 110.0(10) . . ? F3 C4 F2 106.1(9) . . ? F1 C4 F2 104.8(9) . . ? F3 C4 C1 113.0(8) . . ? F1 C4 C1 111.8(7) . . ? F2 C4 C1 110.6(7) . . ? F4 C5 F6 108.2(9) . . ? F4 C5 F5 106.0(9) . . ? F6 C5 F5 105.1(8) . . ? F4 C5 C3 115.0(7) . . ? F6 C5 C3 110.4(8) . . ? F5 C5 C3 111.5(7) . . ? O3 C6 C7 126.8(6) . . ? O3 C6 C9 116.5(7) . . ? C7 C6 C9 116.7(7) . . ? C8 C7 C6 123.9(7) . . ? O4 C8 C7 127.7(7) . . ? O4 C8 C10 114.5(7) . . ? C7 C8 C10 117.7(7) . . ? F9 C9 F7 105.6(9) . . ? F9 C9 F8 110.2(10) . . ? F7 C9 F8 106.4(9) . . ? F9 C9 C6 109.6(8) . . ? F7 C9 C6 112.9(8) . . ? F8 C9 C6 112.0(8) . . ? F11 C10 F10 112.6(14) . . ? F11 C10 F12 107.0(13) . . ? F10 C10 F12 94.7(10) . . ? F11 C10 C8 116.7(7) . . ? F10 C10 C8 111.8(10) . . ? F12 C10 C8 111.7(11) . . ? C15 C11 N1 111.3(6) . . ? C15 C11 C14 111.3(8) . . ? N1 C11 C14 106.5(6) . . ? C15 C11 C12 115.4(7) . . ? N1 C11 C12 99.2(5) . . ? C14 C11 C12 112.3(6) . . ? N2 C12 C17 111.1(5) . . ? N2 C12 C16 105.2(7) . . ? C17 C12 C16 111.4(7) . . ? N2 C12 C11 100.5(5) . . ? C17 C12 C11 115.7(7) . . ? C16 C12 C11 111.9(6) . . ? N2 C13 N1 107.1(5) . . ? N2 C13 C18 128.7(5) . . ? N1 C13 C18 124.2(5) . . ? C19 C18 C23 119.3(6) . . ? C19 C18 C13 121.0(5) . . ? C23 C18 C13 119.7(6) . . ? C18 C19 C20 121.6(7) . . ? C21 C20 C19 119.3(8) . . ? C22 C21 C20 119.1(7) . . ? C22 C21 C24 120.0(9) . . ? C20 C21 C24 120.9(10) . . ? C21 C22 C23 122.3(8) . . ? C22 C23 C18 118.3(8) . . ? _refine_diff_density_max .368 _refine_diff_density_min -.503 _refine_diff_density_rms .074 data_3 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C48.50 H42 Cl1.50 F24 Mn2 N4 O12' _chemical_formula_weight 1491.92 _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' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' .3368 .7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/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 27.342(4) _cell_length_b 13.973(4) _cell_length_c 22.922(3) _cell_angle_alpha 89.94(2) _cell_angle_beta 125.794(12) _cell_angle_gamma 90.03(2) _cell_volume 7103.3(25) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.02 _cell_measurement_theta_max 12.52 _exptl_crystal_description needle _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method ? _exptl_crystal_F_000 2994 _exptl_absorpt_coefficient_mu 0.526 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 'none' _exptl_absorpt_correction_T_max 'none' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method omega-2theta _diffrn_standards_number 80 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4985 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.1352 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 24.29 _reflns_number_total 4896 _reflns_number_observed 2230 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR92 (Giacovazzo, 1992)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+( 0.2530P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4895 _refine_ls_number_parameters 397 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2324 _refine_ls_R_factor_obs 0.1070 _refine_ls_wR_factor_all 0.3975 _refine_ls_wR_factor_obs 0.2968 _refine_ls_goodness_of_fit_all 1.044 _refine_ls_goodness_of_fit_obs 1.184 _refine_ls_restrained_S_all 1.045 _refine_ls_restrained_S_obs 1.184 _refine_ls_shift/esd_max -1.262 _refine_ls_shift/esd_mean 0.106 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 Mn1 Mn 0.28346(8) 0.02345(12) 0.71708(9) 0.0550(6) Uani 1 d . . O1 O 0.2155(4) 0.1176(5) 0.6988(4) 0.060(2) Uani 1 d . . O6 O 0.2456(4) 0.4465(5) 0.7292(4) 0.061(2) Uani 1 d . . O2 O 0.3395(4) -0.0964(6) 0.7341(4) 0.074(2) Uani 1 d . . O3 O 0.2280(4) -0.0318(6) 0.6095(4) 0.069(2) Uani 1 d . . O4 O 0.3661(4) 0.0774(6) 0.8140(4) 0.067(2) Uani 1 d . . O5 O 0.3121(4) 0.1203(6) 0.6699(4) 0.078(2) Uani 1 d . . N1 N 0.2112(4) 0.2098(6) 0.6848(5) 0.055(2) Uani 1 d . . N2 N 0.2251(4) 0.3623(6) 0.6985(5) 0.056(2) Uani 1 d . . C1 C 0.2422(5) 0.2769(7) 0.7349(6) 0.051(3) Uani 1 d . . C2 C 0.1881(6) 0.3510(8) 0.6186(6) 0.065(3) Uani 1 d . . C3 C 0.1630(5) 0.2481(8) 0.6109(6) 0.057(3) Uani 1 d . . C21 C 0.1402(7) 0.4287(10) 0.5827(8) 0.099(5) Uani 1 d . . H21A H 0.1185(35) 0.4302(55) 0.6038(43) 0.149 Uiso 1 calc R . H21B H 0.1127(31) 0.4154(46) 0.5322(13) 0.149 Uiso 1 calc R . H21C H 0.1590(9) 0.4896(15) 0.5894(54) 0.149 Uiso 1 calc R . C22 C 0.2335(8) 0.3593(10) 0.6032(8) 0.103(5) Uani 1 d . . H22A H 0.2137(9) 0.3576(89) 0.5522(8) 0.154 Uiso 1 calc R . H22B H 0.2615(33) 0.3070(50) 0.6254(56) 0.154 Uiso 1 calc R . H22C H 0.2549(39) 0.4187(42) 0.6221(59) 0.154 Uiso 1 calc R . C31 C 0.1043(6) 0.2446(10) 0.6024(8) 0.087(4) Uani 1 d . . H31A H 0.0727(10) 0.2697(67) 0.5561(22) 0.130 Uiso 1 calc R . H31B H 0.1074(16) 0.2823(58) 0.6394(33) 0.130 Uiso 1 calc R . H31C H 0.0952(23) 0.1795(13) 0.6062(54) 0.130 Uiso 1 calc R . C32 C 0.1600(7) 0.1863(10) 0.5544(7) 0.092(5) Uani 1 d . . H32A H 0.1357(40) 0.2176(37) 0.5085(13) 0.137 Uiso 1 calc R . H32B H 0.1424(45) 0.1255(30) 0.5518(41) 0.137 Uiso 1 calc R . H32C H 0.1999(9) 0.1766(63) 0.5672(30) 0.137 Uiso 1 calc R . C4 C 0.2868(6) 0.2641(8) 0.8113(7) 0.058(3) Uani 1 d . . C5 C 0.3404(6) 0.3165(9) 0.8498(7) 0.075(4) Uani 1 d . . H5 H 0.3480(6) 0.3620(9) 0.8263(7) 0.090 Uiso 1 calc R . C6 C 0.3821(8) 0.3008(12) 0.9223(9) 0.100(5) Uani 1 d . . H6 H 0.4177(8) 0.3361(12) 0.9471(9) 0.120 Uiso 1 calc R . C7 C 0.3729(9) 0.2357(15) 0.9583(8) 0.103(6) Uani 1 d . . C8 C 0.3195(9) 0.1860(10) 0.9211(8) 0.088(5) Uani 1 d . . H8 H 0.3117(9) 0.1426(10) 0.9455(8) 0.106 Uiso 1 calc R . C9 C 0.2768(7) 0.1993(9) 0.8478(7) 0.074(4) Uani 1 d . . H9 H 0.2413(7) 0.1638(9) 0.8235(7) 0.089 Uiso 1 calc R . C10 C 0.4203(9) 0.2197(16) 1.0364(8) 0.151(9) Uani 1 d . . H10A H 0.4262(55) 0.2775(39) 1.0624(14) 0.227 Uiso 1 calc R . H10B H 0.4574(22) 0.2020(121) 1.0436(13) 0.227 Uiso 1 calc R . H10C H 0.4078(36) 0.1694(84) 1.0535(22) 0.227 Uiso 1 calc R . C11 C 0.3429(6) -0.1313(10) 0.6864(7) 0.075(4) Uiso 1 d . . C12 C 0.3018(7) -0.1236(10) 0.6126(8) 0.084(4) Uiso 1 d . . H12 H 0.3111(7) -0.1528(10) 0.5837(8) 0.101 Uiso 1 calc R . C13 C 0.2487(6) -0.0755(9) 0.5801(7) 0.067(3) Uiso 1 d . . C14 C 0.4118(25) -0.1627(44) 0.7139(17) 0.383(41) Uani 1 d . . C15 C 0.2079(10) -0.0678(14) 0.5001(9) 0.105(5) Uani 1 d . . C16 C 0.4131(7) 0.1043(10) 0.8205(8) 0.077(4) Uiso 1 d . . C17 C 0.4165(7) 0.1366(10) 0.7683(8) 0.088(4) Uiso 1 d . . H17 H 0.4536(7) 0.1573(10) 0.7802(8) 0.105 Uiso 1 calc R . C18 C 0.3655(7) 0.1408(10) 0.6948(8) 0.079(4) Uiso 1 d . . C19 C 0.4698(8) 0.0993(15) 0.8945(9) 0.102(5) Uani 1 d . . C20 C 0.3750(11) 0.1701(21) 0.6395(14) 0.132(8) Uani 1 d . . F11 F 0.4459(7) -0.1660(25) 0.7777(12) 0.268(12) Uani 1 d . . F12 F 0.4129(9) -0.2176(19) 0.6784(8) 0.280(13) Uani 1 d . . F13 F 0.3956(14) -0.2702(21) 0.7437(19) 0.325(16) Uani 1 d . . F21 F 0.2171(9) -0.0031(16) 0.4740(6) 0.315(16) Uani 1 d . . F22 F 0.1499(6) -0.0643(13) 0.4708(6) 0.180(6) Uani 1 d . . F23 F 0.2065(9) -0.1447(12) 0.4676(7) 0.248(10) Uani 1 d . . F31 F 0.5016(7) 0.0299(13) 0.9045(7) 0.236(10) Uani 1 d . . F32 F 0.5049(6) 0.1754(12) 0.9128(6) 0.204(8) Uani 1 d . . F33 F 0.4644(4) 0.0984(10) 0.9456(5) 0.141(4) Uani 1 d . . F41 F 0.4273(6) 0.1967(14) 0.6632(7) 0.203(7) Uani 1 d . . F42 F 0.3354(8) 0.2293(16) 0.5942(10) 0.266(12) Uani 1 d . . F43 F 0.3703(11) 0.0981(15) 0.5997(11) 0.239(10) Uani 1 d . . C90 C 0.4588(31) -0.5821(42) 0.8285(31) 0.218(50) Uiso 0.25 d PD . Cl1 Cl 0.4022(25) -0.4901(36) 0.7882(29) 0.298(21) Uiso 0.25 d PD . Cl2 Cl 0.4936(21) -0.5133(31) 0.9077(25) 0.256(18) Uiso 0.25 d PD . Cl3 Cl 0.4875(37) -0.5082(54) 0.7937(41) 0.396(37) Uiso 0.25 d PD . 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 Mn1 0.0640(12) 0.0375(9) 0.0546(11) -0.0017(8) 0.0297(10) -0.0010(9) O1 0.077(6) 0.031(4) 0.068(5) 0.003(4) 0.040(5) 0.000(4) O6 0.085(6) 0.031(4) 0.069(5) -0.007(4) 0.046(5) -0.002(4) O2 0.083(6) 0.068(5) 0.063(5) -0.004(4) 0.040(5) 0.013(5) O3 0.068(5) 0.064(5) 0.066(5) -0.004(4) 0.034(5) 0.001(4) O4 0.066(6) 0.065(5) 0.057(5) -0.003(4) 0.028(5) 0.000(4) O5 0.062(6) 0.085(6) 0.070(6) 0.016(5) 0.028(5) -0.008(5) N1 0.064(6) 0.027(5) 0.058(6) 0.006(5) 0.028(5) 0.007(4) N2 0.075(7) 0.035(5) 0.055(6) -0.004(4) 0.037(5) 0.000(5) C1 0.076(8) 0.033(6) 0.051(7) -0.005(6) 0.041(7) -0.008(6) C2 0.094(10) 0.033(6) 0.060(8) -0.004(5) 0.040(8) 0.001(6) C3 0.056(8) 0.045(6) 0.055(7) 0.004(5) 0.023(7) -0.002(6) C21 0.123(14) 0.059(9) 0.066(9) 0.000(7) 0.027(10) 0.023(9) C22 0.178(17) 0.061(9) 0.100(11) -0.017(8) 0.098(13) -0.019(10) C31 0.080(10) 0.070(9) 0.083(10) -0.001(8) 0.033(9) 0.006(8) C32 0.128(13) 0.071(9) 0.058(8) -0.013(7) 0.044(9) -0.002(9) C4 0.077(9) 0.044(7) 0.066(8) 0.008(6) 0.048(8) 0.012(6) C5 0.072(9) 0.062(9) 0.058(9) 0.004(7) 0.021(8) 0.006(8) C6 0.098(13) 0.090(12) 0.088(13) 0.003(9) 0.041(12) 0.009(10) C7 0.124(16) 0.111(14) 0.067(11) -0.008(10) 0.051(12) 0.036(12) C8 0.131(15) 0.071(10) 0.068(10) 0.027(8) 0.062(11) 0.023(10) C9 0.094(10) 0.059(8) 0.074(9) 0.004(7) 0.052(9) 0.005(7) C10 0.155(19) 0.180(20) 0.061(11) 0.007(12) 0.030(12) 0.060(16) C14 0.421(56) 0.493(72) 0.088(20) 0.018(29) 0.065(30) 0.397(58) C15 0.119(16) 0.116(14) 0.064(11) -0.030(10) 0.044(12) -0.025(12) C19 0.082(12) 0.122(15) 0.063(11) 0.012(10) 0.020(10) 0.006(12) C20 0.110(17) 0.173(22) 0.152(20) 0.033(18) 0.098(17) -0.004(15) F11 0.143(13) 0.424(35) 0.168(17) -0.050(18) 0.051(12) 0.139(18) F12 0.263(18) 0.467(32) 0.151(12) 0.065(16) 0.144(13) 0.242(21) F13 0.284(30) 0.335(31) 0.345(35) 0.090(30) 0.177(29) 0.236(28) F21 0.368(26) 0.382(27) 0.071(8) 0.029(12) 0.058(11) -0.235(22) F22 0.119(10) 0.294(18) 0.069(7) 0.004(8) 0.022(7) 0.001(11) F23 0.327(22) 0.196(15) 0.103(9) -0.058(10) 0.060(11) 0.072(15) F31 0.191(14) 0.237(17) 0.097(9) -0.024(9) -0.020(9) 0.130(14) F32 0.150(11) 0.251(17) 0.096(8) 0.005(9) 0.007(8) -0.111(12) F33 0.098(7) 0.233(14) 0.059(6) 0.002(7) 0.028(6) -0.010(8) F41 0.137(11) 0.365(24) 0.134(10) 0.044(12) 0.094(9) -0.028(13) F42 0.236(17) 0.408(28) 0.273(19) 0.242(21) 0.216(16) 0.162(19) F43 0.352(29) 0.239(20) 0.237(20) -0.062(16) 0.235(22) -0.067(19) _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 Mn1 O6 2.107(7) 4_546 ? Mn1 O1 2.109(8) . ? Mn1 O5 2.145(8) . ? Mn1 O2 2.147(8) . ? Mn1 O3 2.146(8) . ? Mn1 O4 2.177(8) . ? O1 N1 1.317(10) . ? O6 N2 1.315(11) . ? O6 Mn1 2.109(7) 4_556 ? O2 C11 1.249(14) . ? O3 C13 1.263(14) . ? O4 C16 1.259(15) . ? O5 C18 1.25(2) . ? N1 C1 1.334(13) . ? N1 C3 1.509(14) . ? N2 C1 1.372(13) . ? N2 C2 1.497(15) . ? C1 C4 1.44(2) . ? C2 C22 1.48(2) . ? C2 C21 1.52(2) . ? C2 C3 1.56(2) . ? C3 C31 1.50(2) . ? C3 C32 1.52(2) . ? C4 C9 1.36(2) . ? C4 C5 1.40(2) . ? C5 C6 1.38(2) . ? C6 C7 1.35(2) . ? C7 C8 1.37(2) . ? C7 C10 1.49(2) . ? C8 C9 1.39(2) . ? C11 C12 1.38(2) . ? C11 C14 1.66(5) . ? C12 C13 1.36(2) . ? C13 C15 1.49(2) . ? C14 F12 1.13(3) . ? C14 F11 1.19(3) . ? C14 F13 1.81(8) . ? C15 F21 1.19(2) . ? C15 F23 1.29(2) . ? C15 F22 1.31(2) . ? C16 C17 1.33(2) . ? C16 C19 1.49(2) . ? C17 C18 1.43(2) . ? C18 C20 1.49(2) . ? C19 F31 1.23(2) . ? C19 F33 1.26(2) . ? C19 F32 1.33(2) . ? C20 F41 1.25(2) . ? C20 F42 1.27(2) . ? C20 F43 1.31(3) . ? C90 Cl3 1.75(3) . ? C90 Cl2 1.76(3) . ? C90 Cl1 1.80(3) . ? Cl1 Cl3 2.27(9) . ? Cl3 Cl3 2.47(13) 2_656 ? 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 O6 Mn1 O1 81.1(3) 4_546 . ? O6 Mn1 O5 171.5(3) 4_546 . ? O1 Mn1 O5 92.6(3) . . ? O6 Mn1 O2 88.2(3) 4_546 . ? O1 Mn1 O2 167.2(3) . . ? O5 Mn1 O2 98.7(3) . . ? O6 Mn1 O3 103.5(3) 4_546 . ? O1 Mn1 O3 92.8(3) . . ? O5 Mn1 O3 82.4(3) . . ? O2 Mn1 O3 82.9(3) . . ? O6 Mn1 O4 95.8(3) 4_546 . ? O1 Mn1 O4 104.8(3) . . ? O5 Mn1 O4 80.2(3) . . ? O2 Mn1 O4 83.1(3) . . ? O3 Mn1 O4 155.7(3) . . ? N1 O1 Mn1 126.9(6) . . ? N2 O6 Mn1 125.6(6) . 4_556 ? C11 O2 Mn1 123.8(8) . . ? C13 O3 Mn1 123.5(8) . . ? C16 O4 Mn1 127.1(8) . . ? C18 O5 Mn1 125.9(8) . . ? O1 N1 C1 123.8(9) . . ? O1 N1 C3 121.0(8) . . ? C1 N1 C3 114.6(8) . . ? O6 N2 C1 124.5(9) . . ? O6 N2 C2 121.4(8) . . ? C1 N2 C2 113.4(8) . . ? N1 C1 N2 105.6(9) . . ? N1 C1 C4 128.3(9) . . ? N2 C1 C4 126.1(9) . . ? C22 C2 N2 102.8(11) . . ? C22 C2 C21 113.2(12) . . ? N2 C2 C21 109.8(9) . . ? C22 C2 C3 114.8(10) . . ? N2 C2 C3 100.1(9) . . ? C21 C2 C3 114.5(11) . . ? C31 C3 N1 107.5(10) . . ? C31 C3 C32 110.5(11) . . ? N1 C3 C32 109.4(10) . . ? C31 C3 C2 114.2(10) . . ? N1 C3 C2 99.3(9) . . ? C32 C3 C2 115.1(10) . . ? C9 C4 C5 118.3(12) . . ? C9 C4 C1 119.6(12) . . ? C5 C4 C1 122.1(10) . . ? C6 C5 C4 120.1(14) . . ? C7 C6 C5 121.8(17) . . ? C6 C7 C8 118.2(16) . . ? C6 C7 C10 119.6(21) . . ? C8 C7 C10 122.1(20) . . ? C7 C8 C9 121.4(14) . . ? C4 C9 C8 120.2(14) . . ? O2 C11 C12 128.2(13) . . ? O2 C11 C14 114.9(15) . . ? C12 C11 C14 114.4(16) . . ? C13 C12 C11 123.4(14) . . ? O3 C13 C12 127.9(13) . . ? O3 C13 C15 112.0(13) . . ? C12 C13 C15 120.0(14) . . ? F12 C14 F11 121.8(29) . . ? F12 C14 C11 114.1(44) . . ? F11 C14 C11 112.0(31) . . ? F12 C14 F13 79.9(45) . . ? F11 C14 F13 72.1(37) . . ? C11 C14 F13 83.5(39) . . ? F21 C15 F23 106.6(19) . . ? F21 C15 F22 105.2(21) . . ? F23 C15 F22 96.7(17) . . ? F21 C15 C13 116.4(16) . . ? F23 C15 C13 113.4(17) . . ? F22 C15 C13 116.3(15) . . ? O4 C16 C17 126.5(14) . . ? O4 C16 C19 115.7(13) . . ? C17 C16 C19 117.8(14) . . ? C16 C17 C18 122.8(14) . . ? O5 C18 C17 127.0(13) . . ? O5 C18 C20 114.3(15) . . ? C17 C18 C20 118.7(15) . . ? F31 C19 F33 105.9(17) . . ? F31 C19 F32 105.7(19) . . ? F33 C19 F32 99.8(16) . . ? F31 C19 C16 113.6(17) . . ? F33 C19 C16 116.6(15) . . ? F32 C19 C16 113.8(15) . . ? F41 C20 F42 111.9(22) . . ? F41 C20 F43 98.8(21) . . ? F42 C20 F43 103.9(26) . . ? F41 C20 C18 115.7(21) . . ? F42 C20 C18 112.5(18) . . ? F43 C20 C18 112.6(21) . . ? Cl3 C90 Cl2 91.8(41) . . ? Cl3 C90 Cl1 79.8(39) . . ? Cl2 C90 Cl1 85.6(33) . . ? C90 Cl1 Cl3 49.1(21) . . ? C90 Cl3 Cl3 141.5(35) . 2_656 ? C90 Cl3 Cl1 51.1(21) . . ? Cl3 Cl3 Cl1 135.9(56) 2_656 . ? _refine_diff_density_max .791 _refine_diff_density_min -.689 _refine_diff_density_rms .141