# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Zeric Hulvey' _publ_contact_author_email ZHULVEY@CHEM.UCSB.EDU _publ_section_title ; Ionothermal synthesis of inorganic-organic hybrid materials containing perfluorinated aliphatic dicarboxylate ligands ; loop_ _publ_author_name 'Zeric Hulvey' 'Anthony K. Cheetham' 'Zhuojia Lin' 'Russell E Morris' 'David Wragg' #===END data_co_gtam _database_code_depnum_ccdc_archive 'CCDC 678208' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H30 Co3 F24 N4 O20' _chemical_formula_weight 1423.39 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' Co Co 0.3494 0.9721 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.841(10) _cell_length_b 12.328(7) _cell_length_c 22.472(12) _cell_angle_alpha 90.00 _cell_angle_beta 103.821(9) _cell_angle_gamma 90.00 _cell_volume 4799(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 913 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 24.88 _exptl_crystal_description Block _exptl_crystal_colour Purple _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.970 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2828 _exptl_absorpt_coefficient_mu 1.199 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2559 _exptl_absorpt_correction_T_max 0.3351 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37427 _diffrn_reflns_av_R_equivalents 0.0894 _diffrn_reflns_av_sigmaI/netI 0.0938 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 26.37 _reflns_number_total 9565 _reflns_number_gt 5166 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0902P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9565 _refine_ls_number_parameters 784 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1120 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.912 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.24690(4) 1.07606(5) 0.48959(3) 0.01614(18) Uani 1 1 d D . . Co2 Co 0.24697(4) 0.78537(5) 0.49274(3) 0.01512(18) Uani 1 1 d D . . Co3 Co 0.25128(4) 0.49383(5) 0.50950(3) 0.01581(18) Uani 1 1 d D . . C1 C 0.3405(3) 0.9255(4) 0.4253(2) 0.0180(11) Uani 1 1 d . . . C2 C 0.4061(3) 0.9202(4) 0.3912(2) 0.0203(12) Uani 1 1 d . . . C3 C 0.4638(3) 0.8269(4) 0.4098(2) 0.0204(12) Uani 1 1 d . . . C4 C 0.5356(3) 0.8252(4) 0.3825(2) 0.0195(12) Uani 1 1 d . . . C5 C 0.6049(3) 0.8987(4) 0.4134(2) 0.0190(12) Uani 1 1 d . . . C6 C 0.1144(3) 0.9284(4) 0.4271(2) 0.0173(11) Uani 1 1 d . . . C7 C 0.0282(3) 0.9228(4) 0.3908(2) 0.0221(12) Uani 1 1 d . . . C8 C -0.0185(3) 0.8293(4) 0.4095(2) 0.0186(12) Uani 1 1 d . . . C9 C -0.1073(3) 0.8264(4) 0.3807(3) 0.0216(12) Uani 1 1 d . . . C10 C -0.1583(3) 0.8988(4) 0.4115(2) 0.0183(11) Uani 1 1 d . . . C11 C 0.1636(3) 0.6494(4) 0.5720(2) 0.0200(12) Uani 1 1 d . . . C12 C 0.1068(3) 0.6587(4) 0.6132(2) 0.0189(12) Uani 1 1 d . . . C13 C 0.0323(3) 0.5941(4) 0.5895(2) 0.0180(11) Uani 1 1 d . . . C14 C -0.0364(3) 0.6186(4) 0.6172(2) 0.0213(12) Uani 1 1 d . . . C15 C -0.1060(3) 0.5429(4) 0.5901(2) 0.0202(12) Uani 1 1 d . . . C16 C 0.3778(3) 0.6513(4) 0.5705(2) 0.0187(12) Uani 1 1 d . . . C17 C 0.4612(3) 0.6604(4) 0.6117(2) 0.0190(12) Uani 1 1 d . . . C18 C 0.5201(3) 0.5937(4) 0.5867(2) 0.0190(12) Uani 1 1 d . . . C19 C 0.6050(3) 0.6203(4) 0.6120(2) 0.0207(12) Uani 1 1 d . . . C20 C 0.6594(3) 0.5435(4) 0.5870(2) 0.0193(12) Uani 1 1 d . . . F1 F 0.44625(17) 1.0126(2) 0.39704(15) 0.0284(8) Uani 1 1 d . . . F2 F 0.37101(17) 0.9074(3) 0.33040(13) 0.0286(8) Uani 1 1 d . . . F3 F 0.42600(18) 0.7327(2) 0.39324(16) 0.0346(8) Uani 1 1 d . . . F4 F 0.48891(17) 0.8290(3) 0.47134(14) 0.0341(8) Uani 1 1 d . . . F5 F 0.51252(17) 0.8502(3) 0.32211(14) 0.0292(8) Uani 1 1 d . . . F6 F 0.56113(16) 0.7213(2) 0.38500(15) 0.0300(8) Uani 1 1 d . . . F7 F -0.00868(18) 1.0156(2) 0.39382(17) 0.0400(9) Uani 1 1 d . . . F8 F 0.02868(18) 0.9088(3) 0.33034(14) 0.0378(9) Uani 1 1 d . . . F9 F 0.01054(18) 0.7359(2) 0.39474(17) 0.0405(9) Uani 1 1 d . . . F10 F -0.00838(18) 0.8335(3) 0.47059(15) 0.0392(9) Uani 1 1 d . . . F11 F -0.12984(17) 0.7220(2) 0.38158(15) 0.0305(8) Uani 1 1 d . . . F12 F -0.11838(17) 0.8551(3) 0.32082(14) 0.0299(8) Uani 1 1 d . . . F13 F 0.08813(18) 0.7630(2) 0.62054(15) 0.0305(8) Uani 1 1 d . . . F14 F 0.14126(17) 0.6220(3) 0.67056(13) 0.0304(8) Uani 1 1 d . . . F15 F 0.00943(17) 0.6137(3) 0.52839(13) 0.0291(8) Uani 1 1 d . . . F16 F 0.04818(18) 0.4882(2) 0.59741(15) 0.0322(8) Uani 1 1 d . . . F17 F -0.05815(17) 0.7227(2) 0.60816(15) 0.0290(8) Uani 1 1 d . . . F18 F -0.01328(17) 0.6028(3) 0.67873(13) 0.0281(7) Uani 1 1 d . . . F19 F 0.48432(16) 0.7644(2) 0.61838(14) 0.0278(7) Uani 1 1 d . . . F20 F 0.46135(17) 0.6237(3) 0.66910(13) 0.0268(7) Uani 1 1 d . . . F21 F 0.50313(17) 0.6092(2) 0.52544(13) 0.0251(7) Uani 1 1 d . . . F22 F 0.50907(17) 0.4887(2) 0.59736(14) 0.0277(7) Uani 1 1 d . . . F23 F 0.61894(17) 0.7245(2) 0.59778(14) 0.0248(7) Uani 1 1 d . . . F24 F 0.62067(17) 0.6137(3) 0.67398(13) 0.0283(7) Uani 1 1 d . . . O1 O 0.2307(2) 1.2181(3) 0.43774(16) 0.0191(8) Uani 1 1 d D . . H1A H 0.2663(16) 1.269(2) 0.436(2) 0.035(17) Uiso 1 1 d D . . H1B H 0.1848(15) 1.254(4) 0.426(3) 0.12(4) Uiso 1 1 d D . . O2 O 0.26346(19) 0.9323(3) 0.54377(15) 0.0169(8) Uani 1 1 d D . . H2A H 0.3124(12) 0.9333(16) 0.5669(11) 0.031(17) Uiso 1 1 d D . . H2B H 0.2318(17) 0.9353(16) 0.5689(11) 0.05(2) Uiso 1 1 d D . . O3 O 0.2336(2) 0.6331(3) 0.44829(15) 0.0164(8) Uani 1 1 d D . . H3A H 0.1860(12) 0.6238(16) 0.4244(11) 0.032(17) Uiso 1 1 d D . . H3B H 0.2673(16) 0.6242(16) 0.4255(11) 0.028(16) Uiso 1 1 d D . . O4 O 0.2665(2) 0.3492(3) 0.56127(17) 0.0210(8) Uani 1 1 d D . . H4B H 0.2290(15) 0.303(2) 0.564(2) 0.028(16) Uiso 1 1 d D . . H4A H 0.3094(16) 0.308(3) 0.568(2) 0.05(2) Uiso 1 1 d D . . O5 O 0.3207(2) 1.0181(3) 0.43753(17) 0.0237(9) Uani 1 1 d . . . O6 O 0.3128(2) 0.8366(3) 0.43410(17) 0.0246(9) Uani 1 1 d . . . O7 O 0.6046(2) 0.9929(3) 0.39450(17) 0.0280(9) Uani 1 1 d . . . O8 O 0.6546(2) 0.8522(3) 0.45450(16) 0.0209(8) Uani 1 1 d . . . O9 O 0.1404(2) 1.0204(3) 0.44071(16) 0.0222(8) Uani 1 1 d . . . O10 O 0.1466(2) 0.8394(3) 0.43538(17) 0.0244(9) Uani 1 1 d . . . O11 O -0.1833(2) 0.8513(3) 0.45242(16) 0.0215(8) Uani 1 1 d . . . O12 O -0.1692(2) 0.9926(3) 0.39272(17) 0.0256(9) Uani 1 1 d . . . O13 O 0.1811(2) 0.7358(3) 0.55122(17) 0.0263(9) Uani 1 1 d . . . O14 O 0.1855(2) 0.5553(3) 0.56528(16) 0.0235(9) Uani 1 1 d . . . O15 O -0.1544(2) 0.5829(3) 0.54495(16) 0.0221(8) Uani 1 1 d . . . O16 O -0.1068(2) 0.4536(3) 0.61443(17) 0.0290(9) Uani 1 1 d . . . O17 O 0.3488(2) 0.7376(3) 0.54966(17) 0.0255(9) Uani 1 1 d . . . O18 O 0.3515(2) 0.5577(3) 0.56486(16) 0.0222(8) Uani 1 1 d . . . O19 O 0.6831(2) 0.5827(3) 0.54294(16) 0.0221(8) Uani 1 1 d . . . O20 O 0.6723(2) 0.4551(3) 0.61156(17) 0.0278(9) Uani 1 1 d . . . N2 N 0.2301(3) 0.6401(4) 0.2543(2) 0.0281(11) Uani 1 1 d . . . N1 N 0.1132(3) 0.6605(3) 0.2611(2) 0.0255(11) Uani 1 1 d . . . C21 C 0.1585(3) 0.6114(4) 0.2310(3) 0.0267(13) Uani 1 1 d . . . H21 H 0.1422 0.5638 0.1984 0.032 Uiso 1 1 calc R . . C22 C 0.2319(3) 0.7098(4) 0.3021(2) 0.0272(13) Uani 1 1 d . . . H22 H 0.2754 0.7418 0.3270 0.033 Uiso 1 1 calc R . . C23 C 0.1582(3) 0.7231(4) 0.3061(2) 0.0264(13) Uani 1 1 d . . . H23 H 0.1412 0.7666 0.3340 0.032 Uiso 1 1 calc R . . C24 C 0.0298(3) 0.6479(5) 0.2506(3) 0.0364(15) Uani 1 1 d . . . H24A H 0.0092 0.6215 0.2098 0.055 Uiso 1 1 calc R . . H24B H 0.0069 0.7168 0.2555 0.055 Uiso 1 1 calc R . . H24C H 0.0184 0.5972 0.2796 0.055 Uiso 1 1 calc R . . C25 C 0.2984(4) 0.6067(5) 0.2320(3) 0.0383(16) Uani 1 1 d . . . H25A H 0.2862 0.5419 0.2070 0.046 Uiso 1 1 calc R . . H25B H 0.3408 0.5897 0.2666 0.046 Uiso 1 1 calc R . . C26 C 0.3221(4) 0.6962(5) 0.1947(3) 0.0428(17) Uani 1 1 d . . . H26A H 0.2780 0.7197 0.1638 0.064 Uiso 1 1 calc R . . H26B H 0.3611 0.6699 0.1754 0.064 Uiso 1 1 calc R . . H26C H 0.3421 0.7561 0.2210 0.064 Uiso 1 1 calc R . . N3 N 0.2831(3) 0.1225(4) 0.2579(2) 0.0307(12) Uani 1 1 d . . . N4 N 0.3969(3) 0.0990(4) 0.2427(2) 0.0304(12) Uani 1 1 d . . . C27 C 0.3583(4) 0.1316(4) 0.2820(3) 0.0311(14) Uani 1 1 d . . . H27 H 0.3803 0.1573 0.3212 0.037 Uiso 1 1 calc R . . C28 C 0.2742(3) 0.0803(4) 0.1999(3) 0.0291(14) Uani 1 1 d . . . H28 H 0.2278 0.0645 0.1722 0.035 Uiso 1 1 calc R . . C29 C 0.3453(3) 0.0665(4) 0.1906(3) 0.0294(13) Uani 1 1 d . . . H29 H 0.3572 0.0397 0.1553 0.035 Uiso 1 1 calc R . . C30 C 0.4811(4) 0.0977(5) 0.2526(3) 0.0398(16) Uani 1 1 d . . . H30A H 0.4995 0.1704 0.2501 0.060 Uiso 1 1 calc R . . H30B H 0.4953 0.0536 0.2218 0.060 Uiso 1 1 calc R . . H30C H 0.5037 0.0684 0.2924 0.060 Uiso 1 1 calc R . . C31 C 0.2230(4) 0.1510(5) 0.2890(3) 0.0414(17) Uani 1 1 d . . . H31A H 0.1917 0.2089 0.2667 0.050 Uiso 1 1 calc R . . H31B H 0.2468 0.1776 0.3298 0.050 Uiso 1 1 calc R . . C32 C 0.1727(4) 0.0567(6) 0.2939(3) 0.056(2) Uani 1 1 d . . . H32A H 0.1430 0.0373 0.2538 0.084 Uiso 1 1 calc R . . H32B H 0.1385 0.0757 0.3194 0.084 Uiso 1 1 calc R . . H32C H 0.2041 -0.0037 0.3116 0.084 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 Co1 0.0138(4) 0.0137(4) 0.0212(4) -0.0003(3) 0.0046(3) -0.0001(3) Co2 0.0111(4) 0.0123(3) 0.0222(4) 0.0003(3) 0.0046(3) 0.0000(3) Co3 0.0121(4) 0.0144(3) 0.0211(4) -0.0002(3) 0.0044(3) -0.0003(3) C1 0.015(3) 0.021(3) 0.019(3) 0.001(2) 0.005(2) 0.001(2) C2 0.017(3) 0.019(3) 0.024(3) 0.003(2) 0.004(2) 0.002(2) C3 0.013(3) 0.022(3) 0.024(3) 0.001(2) 0.001(2) -0.001(2) C4 0.013(3) 0.017(3) 0.030(3) -0.003(2) 0.009(2) 0.005(2) C5 0.015(3) 0.024(3) 0.018(3) -0.003(2) 0.004(2) 0.001(2) C6 0.010(3) 0.023(3) 0.019(3) 0.002(2) 0.002(2) -0.001(2) C7 0.014(3) 0.023(3) 0.027(3) -0.002(2) 0.000(2) -0.001(2) C8 0.010(3) 0.022(3) 0.024(3) 0.002(2) 0.004(2) 0.001(2) C9 0.012(3) 0.017(3) 0.035(3) -0.002(2) 0.003(2) -0.004(2) C10 0.013(3) 0.023(3) 0.019(3) -0.004(2) 0.003(2) -0.006(2) C11 0.011(3) 0.026(3) 0.022(3) -0.003(2) 0.001(2) -0.008(2) C12 0.020(3) 0.018(3) 0.020(3) 0.000(2) 0.007(2) 0.003(2) C13 0.016(3) 0.014(3) 0.023(3) 0.004(2) 0.003(2) 0.000(2) C14 0.018(3) 0.018(3) 0.026(3) -0.004(2) 0.001(2) 0.002(2) C15 0.010(3) 0.029(3) 0.020(3) -0.006(2) 0.001(2) -0.003(2) C16 0.015(3) 0.021(3) 0.022(3) -0.004(2) 0.008(2) 0.006(2) C17 0.021(3) 0.015(3) 0.019(3) -0.001(2) 0.001(2) -0.001(2) C18 0.020(3) 0.015(3) 0.022(3) 0.002(2) 0.005(2) 0.004(2) C19 0.024(3) 0.017(3) 0.022(3) -0.005(2) 0.007(2) -0.002(2) C20 0.009(3) 0.026(3) 0.025(3) -0.006(2) 0.007(2) -0.002(2) F1 0.0234(18) 0.0179(16) 0.049(2) -0.0021(14) 0.0192(16) -0.0069(13) F2 0.0215(18) 0.044(2) 0.0199(17) 0.0012(14) 0.0040(14) 0.0039(15) F3 0.0218(18) 0.0197(17) 0.065(2) -0.0035(16) 0.0156(17) -0.0065(14) F4 0.0214(18) 0.051(2) 0.0299(19) 0.0121(16) 0.0059(15) 0.0052(16) F5 0.0233(18) 0.043(2) 0.0223(18) -0.0057(14) 0.0070(14) -0.0016(15) F6 0.0169(17) 0.0153(16) 0.057(2) -0.0117(15) 0.0067(16) -0.0009(13) F7 0.0174(18) 0.0212(18) 0.076(3) 0.0017(17) 0.0009(17) 0.0033(14) F8 0.0247(19) 0.067(2) 0.0213(18) 0.0050(16) 0.0041(15) -0.0102(17) F9 0.0233(19) 0.0183(17) 0.081(3) -0.0051(17) 0.0146(18) 0.0043(14) F10 0.0224(19) 0.070(2) 0.0257(19) 0.0105(17) 0.0066(15) -0.0013(17) F11 0.0217(18) 0.0183(16) 0.055(2) -0.0082(15) 0.0153(16) -0.0033(13) F12 0.0198(18) 0.049(2) 0.0206(18) -0.0056(15) 0.0034(14) 0.0022(15) F13 0.0256(18) 0.0255(17) 0.046(2) -0.0102(15) 0.0186(16) -0.0070(14) F14 0.0198(18) 0.052(2) 0.0178(17) 0.0039(15) 0.0010(14) -0.0025(15) F15 0.0218(18) 0.0427(19) 0.0217(18) -0.0044(15) 0.0029(14) -0.0082(15) F16 0.0259(19) 0.0189(17) 0.057(2) -0.0027(15) 0.0204(17) -0.0026(14) F17 0.0190(17) 0.0157(16) 0.053(2) -0.0040(14) 0.0095(15) 0.0022(13) F18 0.0244(18) 0.0413(19) 0.0181(17) -0.0059(14) 0.0043(14) -0.0067(15) F19 0.0176(17) 0.0226(17) 0.041(2) -0.0096(14) 0.0025(15) 0.0009(13) F20 0.0198(17) 0.046(2) 0.0159(17) 0.0032(14) 0.0061(14) 0.0045(14) F21 0.0227(18) 0.0344(17) 0.0184(17) -0.0035(13) 0.0051(14) 0.0052(14) F22 0.0208(17) 0.0181(16) 0.044(2) 0.0004(14) 0.0073(15) 0.0040(13) F23 0.0215(17) 0.0174(16) 0.0390(19) -0.0034(13) 0.0141(14) -0.0030(13) F24 0.0232(18) 0.0410(19) 0.0194(17) -0.0059(14) 0.0025(14) 0.0028(15) O1 0.017(2) 0.0180(19) 0.022(2) 0.0018(16) 0.0045(17) -0.0025(17) O2 0.012(2) 0.0168(18) 0.021(2) 0.0014(15) 0.0025(17) 0.0002(14) O3 0.015(2) 0.0162(18) 0.019(2) -0.0002(14) 0.0054(17) 0.0015(14) O4 0.018(2) 0.0191(19) 0.026(2) 0.0050(16) 0.0044(17) -0.0020(17) O5 0.021(2) 0.018(2) 0.036(2) 0.0018(16) 0.0145(18) 0.0002(15) O6 0.025(2) 0.0164(19) 0.038(2) -0.0023(17) 0.0188(18) -0.0017(16) O7 0.017(2) 0.025(2) 0.038(2) 0.0064(18) -0.0012(18) -0.0055(16) O8 0.015(2) 0.0191(19) 0.028(2) -0.0011(16) 0.0033(17) -0.0018(15) O9 0.015(2) 0.017(2) 0.033(2) 0.0006(16) 0.0012(17) 0.0004(15) O10 0.015(2) 0.018(2) 0.037(2) -0.0029(16) -0.0006(17) 0.0016(16) O11 0.017(2) 0.0166(19) 0.031(2) -0.0003(16) 0.0058(17) 0.0010(15) O12 0.022(2) 0.023(2) 0.034(2) 0.0057(17) 0.0138(18) 0.0078(16) O13 0.028(2) 0.022(2) 0.033(2) -0.0002(17) 0.0156(18) -0.0035(17) O14 0.023(2) 0.020(2) 0.031(2) 0.0023(16) 0.0130(17) 0.0055(16) O15 0.016(2) 0.021(2) 0.028(2) 0.0001(16) 0.0017(17) -0.0040(15) O16 0.023(2) 0.027(2) 0.034(2) 0.0080(18) 0.0020(18) -0.0048(17) O17 0.018(2) 0.021(2) 0.033(2) -0.0025(17) -0.0024(17) 0.0050(16) O18 0.016(2) 0.022(2) 0.025(2) 0.0024(16) -0.0029(16) -0.0049(16) O19 0.024(2) 0.0190(19) 0.025(2) -0.0011(15) 0.0098(17) 0.0047(15) O20 0.026(2) 0.025(2) 0.036(2) 0.0086(18) 0.0147(19) 0.0063(17) N2 0.029(3) 0.028(3) 0.027(3) 0.008(2) 0.004(2) 0.004(2) N1 0.029(3) 0.023(2) 0.023(3) 0.002(2) 0.002(2) 0.000(2) C21 0.034(4) 0.020(3) 0.024(3) 0.001(2) 0.004(3) 0.001(3) C22 0.031(4) 0.028(3) 0.021(3) 0.000(2) 0.003(3) -0.007(3) C23 0.034(4) 0.027(3) 0.017(3) -0.001(2) 0.006(3) 0.004(3) C24 0.033(4) 0.043(4) 0.035(4) 0.001(3) 0.011(3) -0.003(3) C25 0.035(4) 0.043(4) 0.038(4) 0.003(3) 0.010(3) 0.011(3) C26 0.036(4) 0.058(4) 0.036(4) 0.007(3) 0.013(3) 0.001(3) N3 0.039(3) 0.027(3) 0.028(3) -0.001(2) 0.013(2) 0.002(2) N4 0.032(3) 0.025(3) 0.030(3) 0.001(2) 0.000(2) -0.002(2) C27 0.038(4) 0.024(3) 0.029(4) -0.003(3) 0.004(3) 0.003(3) C28 0.028(3) 0.035(3) 0.021(3) 0.000(3) -0.001(3) -0.004(3) C29 0.033(4) 0.033(3) 0.022(3) -0.001(3) 0.006(3) 0.002(3) C30 0.039(4) 0.041(4) 0.037(4) -0.005(3) 0.006(3) -0.008(3) C31 0.049(4) 0.041(4) 0.041(4) 0.005(3) 0.024(3) 0.011(3) C32 0.044(5) 0.074(5) 0.051(5) 0.002(4) 0.014(4) -0.006(4) _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 O9 2.070(4) . ? Co1 O1 2.085(3) . ? Co1 O5 2.085(4) . ? Co1 O8 2.096(4) 3_676 ? Co1 O11 2.120(4) 3_576 ? Co1 O2 2.131(3) . ? Co2 O17 2.043(4) . ? Co2 O10 2.052(4) . ? Co2 O13 2.053(4) . ? Co2 O6 2.063(4) . ? Co2 O3 2.113(3) . ? Co2 O2 2.126(3) . ? Co3 O14 2.055(4) . ? Co3 O18 2.074(3) . ? Co3 O19 2.075(3) 3_666 ? Co3 O15 2.091(4) 3_566 ? Co3 O4 2.111(4) . ? Co3 O3 2.175(3) . ? C1 O6 1.237(6) . ? C1 O5 1.244(6) . ? C1 C2 1.548(7) . ? C2 F1 1.335(6) . ? C2 F2 1.369(6) . ? C2 C3 1.533(7) . ? C3 F4 1.348(6) . ? C3 F3 1.350(6) . ? C3 C4 1.548(7) . ? C4 F6 1.355(6) . ? C4 F5 1.356(6) . ? C4 C5 1.556(7) . ? C5 O7 1.236(6) . ? C5 O8 1.256(6) . ? C6 O10 1.231(6) . ? C6 O9 1.236(6) . ? C6 C7 1.562(7) . ? C7 F7 1.328(6) . ? C7 F8 1.371(6) . ? C7 C8 1.539(7) . ? C8 F9 1.336(6) . ? C8 F10 1.341(6) . ? C8 C9 1.562(7) . ? C9 F11 1.349(6) . ? C9 F12 1.360(6) . ? C9 C10 1.551(7) . ? C10 O12 1.230(6) . ? C10 O11 1.258(6) . ? C11 O13 1.234(6) . ? C11 O14 1.245(6) . ? C11 C12 1.530(7) . ? C12 F13 1.347(6) . ? C12 F14 1.366(6) . ? C12 C13 1.532(7) . ? C13 F16 1.339(5) . ? C13 F15 1.358(6) . ? C13 C14 1.531(7) . ? C14 F17 1.342(6) . ? C14 F18 1.358(6) . ? C14 C15 1.556(7) . ? C15 O16 1.230(6) . ? C15 O15 1.265(6) . ? C16 O17 1.226(6) . ? C16 O18 1.241(6) . ? C16 C17 1.558(7) . ? C17 F19 1.344(6) . ? C17 F20 1.367(6) . ? C17 C18 1.542(7) . ? C18 F22 1.339(5) . ? C18 F21 1.351(6) . ? C18 C19 1.520(7) . ? C19 F24 1.355(6) . ? C19 F23 1.361(6) . ? C19 C20 1.555(7) . ? C20 O20 1.219(6) . ? C20 O19 1.261(6) . ? O8 Co1 2.096(4) 3_676 ? O11 Co1 2.120(4) 3_576 ? O15 Co3 2.091(4) 3_566 ? O19 Co3 2.075(3) 3_666 ? N2 C21 1.308(7) . ? N2 C22 1.371(7) . ? N2 C25 1.482(7) . ? N1 C21 1.319(7) . ? N1 C23 1.369(7) . ? N1 C24 1.457(7) . ? C22 C23 1.348(8) . ? C25 C26 1.507(8) . ? N3 C27 1.326(7) . ? N3 C28 1.378(7) . ? N3 C31 1.456(7) . ? N4 C27 1.308(7) . ? N4 C29 1.363(7) . ? N4 C30 1.466(7) . ? C28 C29 1.345(8) . ? C31 C32 1.489(9) . ? 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 O9 Co1 O1 89.68(14) . . ? O9 Co1 O5 102.18(15) . . ? O1 Co1 O5 89.79(14) . . ? O9 Co1 O8 171.53(14) . 3_676 ? O1 Co1 O8 88.01(14) . 3_676 ? O5 Co1 O8 85.96(15) . 3_676 ? O9 Co1 O11 84.73(14) . 3_576 ? O1 Co1 O11 88.02(14) . 3_576 ? O5 Co1 O11 172.74(14) . 3_576 ? O8 Co1 O11 87.04(14) 3_676 3_576 ? O9 Co1 O2 90.69(14) . . ? O1 Co1 O2 179.14(13) . . ? O5 Co1 O2 90.90(14) . . ? O8 Co1 O2 91.52(13) 3_676 . ? O11 Co1 O2 91.24(14) 3_576 . ? O17 Co2 O10 177.67(14) . . ? O17 Co2 O13 94.17(16) . . ? O10 Co2 O13 87.25(15) . . ? O17 Co2 O6 86.06(16) . . ? O10 Co2 O6 92.51(15) . . ? O13 Co2 O6 179.46(14) . . ? O17 Co2 O3 91.31(14) . . ? O10 Co2 O3 90.51(14) . . ? O13 Co2 O3 91.21(14) . . ? O6 Co2 O3 89.27(14) . . ? O17 Co2 O2 85.41(14) . . ? O10 Co2 O2 92.85(14) . . ? O13 Co2 O2 86.27(14) . . ? O6 Co2 O2 93.26(14) . . ? O3 Co2 O2 175.70(13) . . ? O14 Co3 O18 91.74(15) . . ? O14 Co3 O19 174.45(14) . 3_666 ? O18 Co3 O19 89.47(15) . 3_666 ? O14 Co3 O15 90.62(15) . 3_566 ? O18 Co3 O15 175.36(14) . 3_566 ? O19 Co3 O15 87.80(14) 3_666 3_566 ? O14 Co3 O4 89.56(14) . . ? O18 Co3 O4 90.62(14) . . ? O19 Co3 O4 85.01(14) 3_666 . ? O15 Co3 O4 85.41(14) 3_566 . ? O14 Co3 O3 94.44(14) . . ? O18 Co3 O3 93.07(14) . . ? O19 Co3 O3 90.90(14) 3_666 . ? O15 Co3 O3 90.73(13) 3_566 . ? O4 Co3 O3 174.47(13) . . ? O6 C1 O5 129.2(5) . . ? O6 C1 C2 114.8(4) . . ? O5 C1 C2 115.9(4) . . ? F1 C2 F2 107.7(4) . . ? F1 C2 C3 107.7(4) . . ? F2 C2 C3 107.7(4) . . ? F1 C2 C1 111.5(4) . . ? F2 C2 C1 106.2(4) . . ? C3 C2 C1 115.7(4) . . ? F4 C3 F3 108.7(4) . . ? F4 C3 C2 107.6(4) . . ? F3 C3 C2 108.2(4) . . ? F4 C3 C4 107.6(4) . . ? F3 C3 C4 106.5(4) . . ? C2 C3 C4 117.9(4) . . ? F6 C4 F5 106.0(4) . . ? F6 C4 C3 107.4(4) . . ? F5 C4 C3 108.1(4) . . ? F6 C4 C5 108.0(4) . . ? F5 C4 C5 109.4(4) . . ? C3 C4 C5 117.4(4) . . ? O7 C5 O8 128.7(5) . . ? O7 C5 C4 117.2(5) . . ? O8 C5 C4 114.1(4) . . ? O10 C6 O9 130.2(5) . . ? O10 C6 C7 113.9(4) . . ? O9 C6 C7 115.8(4) . . ? F7 C7 F8 106.3(4) . . ? F7 C7 C8 108.9(4) . . ? F8 C7 C8 108.0(4) . . ? F7 C7 C6 111.9(4) . . ? F8 C7 C6 106.5(4) . . ? C8 C7 C6 114.8(4) . . ? F9 C8 F10 108.8(4) . . ? F9 C8 C7 108.1(4) . . ? F10 C8 C7 107.6(4) . . ? F9 C8 C9 107.0(4) . . ? F10 C8 C9 107.4(4) . . ? C7 C8 C9 117.7(4) . . ? F11 C9 F12 106.8(4) . . ? F11 C9 C10 109.5(4) . . ? F12 C9 C10 109.2(4) . . ? F11 C9 C8 107.0(4) . . ? F12 C9 C8 107.3(4) . . ? C10 C9 C8 116.5(4) . . ? O12 C10 O11 129.3(5) . . ? O12 C10 C9 116.7(4) . . ? O11 C10 C9 114.0(4) . . ? O13 C11 O14 130.0(5) . . ? O13 C11 C12 115.4(5) . . ? O14 C11 C12 114.6(4) . . ? F13 C12 F14 105.6(4) . . ? F13 C12 C11 111.4(4) . . ? F14 C12 C11 109.4(4) . . ? F13 C12 C13 108.6(4) . . ? F14 C12 C13 108.2(4) . . ? C11 C12 C13 113.3(4) . . ? F16 C13 F15 108.0(4) . . ? F16 C13 C14 107.6(4) . . ? F15 C13 C14 107.5(4) . . ? F16 C13 C12 108.8(4) . . ? F15 C13 C12 106.6(4) . . ? C14 C13 C12 118.0(4) . . ? F17 C14 F18 107.4(4) . . ? F17 C14 C13 110.9(4) . . ? F18 C14 C13 107.9(4) . . ? F17 C14 C15 109.8(4) . . ? F18 C14 C15 109.4(4) . . ? C13 C14 C15 111.4(4) . . ? O16 C15 O15 128.9(5) . . ? O16 C15 C14 117.1(5) . . ? O15 C15 C14 114.1(5) . . ? O17 C16 O18 130.8(5) . . ? O17 C16 C17 114.9(4) . . ? O18 C16 C17 114.3(4) . . ? F19 C17 F20 106.2(4) . . ? F19 C17 C18 109.4(4) . . ? F20 C17 C18 108.6(4) . . ? F19 C17 C16 111.0(4) . . ? F20 C17 C16 108.8(4) . . ? C18 C17 C16 112.6(4) . . ? F22 C18 F21 108.2(4) . . ? F22 C18 C19 108.5(4) . . ? F21 C18 C19 108.2(4) . . ? F22 C18 C17 107.9(4) . . ? F21 C18 C17 106.8(4) . . ? C19 C18 C17 117.0(4) . . ? F24 C19 F23 107.1(4) . . ? F24 C19 C18 108.3(4) . . ? F23 C19 C18 109.7(4) . . ? F24 C19 C20 110.0(4) . . ? F23 C19 C20 108.9(4) . . ? C18 C19 C20 112.7(4) . . ? O20 C20 O19 129.5(5) . . ? O20 C20 C19 116.5(5) . . ? O19 C20 C19 114.0(5) . . ? Co2 O2 Co1 114.71(16) . . ? Co2 O3 Co3 114.79(16) . . ? C1 O5 Co1 133.5(3) . . ? C1 O6 Co2 133.1(3) . . ? C5 O8 Co1 126.3(3) . 3_676 ? C6 O9 Co1 132.7(3) . . ? C6 O10 Co2 133.6(3) . . ? C10 O11 Co1 126.0(3) . 3_576 ? C11 O13 Co2 137.3(3) . . ? C11 O14 Co3 131.2(3) . . ? C15 O15 Co3 127.1(3) . 3_566 ? C16 O17 Co2 136.0(3) . . ? C16 O18 Co3 131.7(3) . . ? C20 O19 Co3 127.7(3) . 3_666 ? C21 N2 C22 108.7(5) . . ? C21 N2 C25 126.4(5) . . ? C22 N2 C25 125.0(5) . . ? C21 N1 C23 108.2(5) . . ? C21 N1 C24 126.6(5) . . ? C23 N1 C24 125.2(5) . . ? N2 C21 N1 109.4(5) . . ? C23 C22 N2 106.7(5) . . ? C22 C23 N1 107.0(5) . . ? N2 C25 C26 110.3(5) . . ? C27 N3 C28 107.2(5) . . ? C27 N3 C31 124.9(5) . . ? C28 N3 C31 127.9(5) . . ? C27 N4 C29 108.3(5) . . ? C27 N4 C30 125.9(5) . . ? C29 N4 C30 125.8(5) . . ? N4 C27 N3 110.0(5) . . ? C29 C28 N3 107.1(5) . . ? C28 C29 N4 107.4(5) . . ? N3 C31 C32 111.9(5) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 2.288 _refine_diff_density_min -0.641 _refine_diff_density_rms 0.185 # Attachment 'revised compounds 1 and 2.cif' data_co_fsucc _database_code_depnum_ccdc_archive 'CCDC 678209' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 Co F8 N4 O10' _chemical_formula_weight 693.38 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' Co Co 0.3494 0.9721 '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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.120(2) _cell_length_b 9.214(3) _cell_length_c 9.618(3) _cell_angle_alpha 70.046(4) _cell_angle_beta 87.725(4) _cell_angle_gamma 65.772(4) _cell_volume 688.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Pink-purple _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.7 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.673 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 353 _exptl_absorpt_coefficient_mu 0.737 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5827 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2727 _reflns_number_gt 2469 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0592P)^2^+0.5728P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2727 _refine_ls_number_parameters 206 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 0.5000 0.0000 0.01680(14) Uani 1 2 d S . . F1 F 0.62115(19) -0.09287(17) 0.17081(15) 0.0363(4) Uani 1 1 d . . . F2 F 0.3728(2) -0.05402(18) 0.12911(17) 0.0372(4) Uani 1 1 d . . . F3 F 0.40441(16) 0.72092(15) 0.45155(13) 0.0253(3) Uani 1 1 d . . . F4 F 0.65072(15) 0.56444(17) 0.42355(13) 0.0254(3) Uani 1 1 d . . . O1 O 0.28340(18) 0.6432(2) 0.25499(16) 0.0236(3) Uani 1 1 d . . . O2 O 0.52965(18) 0.24457(19) 0.07326(16) 0.0232(3) Uani 1 1 d . . . O3 O 0.2722(2) 0.2727(2) 0.0670(2) 0.0358(4) Uani 1 1 d . . . O4 O 0.53881(18) 0.49340(19) 0.21737(15) 0.0215(3) Uani 1 1 d . . . OW O 0.75080(18) 0.4113(2) -0.00507(17) 0.0210(3) Uani 1 1 d D . . N1 N 0.0453(2) 0.2067(2) 0.4362(2) 0.0242(4) Uani 1 1 d . . . N2 N 0.0902(2) 0.0618(2) 0.6720(2) 0.0256(4) Uani 1 1 d . . . C1 C 0.4332(2) 0.5708(2) 0.2847(2) 0.0175(4) Uani 1 1 d . . . C2 C 0.4983(2) 0.5732(3) 0.4302(2) 0.0183(4) Uani 1 1 d . . . C3 C 0.4200(3) 0.1953(3) 0.0730(2) 0.0231(5) Uani 1 1 d . . . C4 C 0.4828(3) 0.0095(3) 0.0759(2) 0.0248(5) Uani 1 1 d . . . C5 C -0.0139(3) 0.1997(3) 0.5655(2) 0.0246(5) Uani 1 1 d . . . H5 H -0.1141 0.2799 0.5795 0.048(5) Uiso 1 1 calc R . . C6 C 0.2199(3) -0.0227(3) 0.6090(3) 0.0324(5) Uani 1 1 d . . . H6 H 0.3120 -0.1253 0.6595 0.048(5) Uiso 1 1 calc R . . C7 C 0.1917(3) 0.0673(3) 0.4627(3) 0.0315(5) Uani 1 1 d . . . H7 H 0.2605 0.0398 0.3900 0.048(5) Uiso 1 1 calc R . . C8 C 0.0666(3) 0.0095(3) 0.8305(3) 0.0328(5) Uani 1 1 d . . . H8A H 0.1598 -0.0961 0.8868 0.075(5) Uiso 1 1 calc R . . H8B H -0.0321 -0.0094 0.8425 0.075(5) Uiso 1 1 calc R . . H8C H 0.0565 0.0992 0.8681 0.075(5) Uiso 1 1 calc R . . C9 C -0.0326(3) 0.3429(3) 0.2914(2) 0.0300(5) Uani 1 1 d . . . H9A H -0.1490 0.3683 0.2805 0.036(5) Uiso 1 1 calc R . . H9B H 0.0173 0.3033 0.2101 0.036(5) Uiso 1 1 calc R . . C10 C -0.0151(3) 0.5029(4) 0.2778(3) 0.0387(6) Uani 1 1 d . . . H10A H -0.0681 0.5910 0.1808 0.075(5) Uiso 1 1 calc R . . H10B H 0.1000 0.4785 0.2867 0.075(5) Uiso 1 1 calc R . . H10C H -0.0660 0.5432 0.3572 0.075(5) Uiso 1 1 calc R . . HWA H 0.764(4) 0.386(4) -0.076(3) 0.046(7) Uiso 1 1 d D . . HWB H 0.758(4) 0.497(3) -0.024(4) 0.046(7) Uiso 1 1 d 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 0.0177(2) 0.0175(2) 0.0151(2) -0.00698(15) 0.00263(14) -0.00646(16) F1 0.0500(9) 0.0215(7) 0.0300(7) -0.0061(6) -0.0090(6) -0.0094(6) F2 0.0551(10) 0.0321(8) 0.0410(8) -0.0180(6) 0.0262(7) -0.0317(7) F3 0.0346(7) 0.0171(6) 0.0216(6) -0.0105(5) 0.0026(5) -0.0056(5) F4 0.0234(6) 0.0360(7) 0.0217(6) -0.0099(5) 0.0047(5) -0.0176(6) O1 0.0196(7) 0.0301(8) 0.0204(7) -0.0120(6) 0.0028(6) -0.0072(6) O2 0.0256(8) 0.0191(7) 0.0251(8) -0.0075(6) 0.0006(6) -0.0097(6) O3 0.0282(9) 0.0345(10) 0.0561(12) -0.0260(9) 0.0150(8) -0.0170(8) O4 0.0198(7) 0.0253(8) 0.0174(7) -0.0107(6) 0.0023(6) -0.0052(6) OW 0.0200(8) 0.0230(8) 0.0198(7) -0.0095(6) 0.0032(6) -0.0075(6) N1 0.0208(9) 0.0281(10) 0.0236(9) -0.0124(8) 0.0044(7) -0.0079(8) N2 0.0243(9) 0.0259(10) 0.0233(9) -0.0096(8) 0.0029(7) -0.0069(8) C1 0.0222(10) 0.0166(9) 0.0137(9) -0.0053(7) 0.0034(7) -0.0083(8) C2 0.0185(10) 0.0195(10) 0.0172(10) -0.0090(8) 0.0040(7) -0.0063(8) C3 0.0311(12) 0.0212(11) 0.0203(10) -0.0095(8) 0.0076(9) -0.0129(9) C4 0.0319(12) 0.0223(11) 0.0250(11) -0.0091(9) 0.0077(9) -0.0159(9) C5 0.0220(11) 0.0258(11) 0.0243(11) -0.0104(9) 0.0042(8) -0.0074(9) C6 0.0256(12) 0.0291(12) 0.0335(12) -0.0135(10) 0.0030(10) -0.0012(10) C7 0.0249(12) 0.0341(13) 0.0330(12) -0.0182(10) 0.0070(9) -0.0053(10) C8 0.0345(13) 0.0307(13) 0.0224(11) -0.0049(9) 0.0050(9) -0.0075(11) C9 0.0282(12) 0.0401(14) 0.0206(11) -0.0115(10) 0.0025(9) -0.0128(10) C10 0.0366(14) 0.0421(15) 0.0347(13) -0.0057(11) 0.0047(11) -0.0206(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 Co1 OW 2.0943(16) . ? Co1 OW 2.0943(16) 2_665 ? Co1 O4 2.1105(15) 2_665 ? Co1 O4 2.1105(15) . ? Co1 O2 2.1142(16) . ? Co1 O2 2.1142(16) 2_665 ? F1 C4 1.357(3) . ? F2 C4 1.359(3) . ? F3 C2 1.359(2) . ? F4 C2 1.359(2) . ? O1 C1 1.243(3) . ? O2 C3 1.257(3) . ? O3 C3 1.232(3) . ? O4 C1 1.248(2) . ? OW HWA 0.78(2) . ? OW HWB 0.78(2) . ? N1 C5 1.328(3) . ? N1 C7 1.376(3) . ? N1 C9 1.475(3) . ? N2 C5 1.328(3) . ? N2 C6 1.372(3) . ? N2 C8 1.470(3) . ? C1 C2 1.553(3) . ? C2 C2 1.535(4) 2_666 ? C3 C4 1.557(3) . ? C4 C4 1.534(4) 2_655 ? C5 H5 0.9500 . ? C6 C7 1.339(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.509(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag OW Co1 OW 180.00(9) . 2_665 ? OW Co1 O4 92.45(6) . 2_665 ? OW Co1 O4 87.55(6) 2_665 2_665 ? OW Co1 O4 87.55(6) . . ? OW Co1 O4 92.45(6) 2_665 . ? O4 Co1 O4 180.0 2_665 . ? OW Co1 O2 88.53(6) . . ? OW Co1 O2 91.47(6) 2_665 . ? O4 Co1 O2 86.17(6) 2_665 . ? O4 Co1 O2 93.83(6) . . ? OW Co1 O2 91.47(6) . 2_665 ? OW Co1 O2 88.53(6) 2_665 2_665 ? O4 Co1 O2 93.83(6) 2_665 2_665 ? O4 Co1 O2 86.17(6) . 2_665 ? O2 Co1 O2 180.0 . 2_665 ? C3 O2 Co1 126.39(14) . . ? C1 O4 Co1 125.28(13) . . ? Co1 OW HWA 103(2) . . ? Co1 OW HWB 99(2) . . ? HWA OW HWB 109(3) . . ? C5 N1 C7 107.95(19) . . ? C5 N1 C9 125.31(19) . . ? C7 N1 C9 126.74(19) . . ? C5 N2 C6 108.84(19) . . ? C5 N2 C8 124.8(2) . . ? C6 N2 C8 126.4(2) . . ? O1 C1 O4 129.99(18) . . ? O1 C1 C2 114.89(17) . . ? O4 C1 C2 115.10(17) . . ? F4 C2 F3 106.73(16) . . ? F4 C2 C2 107.8(2) . 2_666 ? F3 C2 C2 107.08(19) . 2_666 ? F4 C2 C1 111.21(16) . . ? F3 C2 C1 110.57(15) . . ? C2 C2 C1 113.1(2) 2_666 . ? O3 C3 O2 129.9(2) . . ? O3 C3 C4 116.0(2) . . ? O2 C3 C4 114.01(19) . . ? F1 C4 F2 106.35(18) . . ? F1 C4 C4 107.6(2) . 2_655 ? F2 C4 C4 107.8(2) . 2_655 ? F1 C4 C3 110.33(18) . . ? F2 C4 C3 109.73(18) . . ? C4 C4 C3 114.6(2) 2_655 . ? N2 C5 N1 108.6(2) . . ? N2 C5 H5 125.7 . . ? N1 C5 H5 125.7 . . ? C7 C6 N2 106.8(2) . . ? C7 C6 H6 126.6 . . ? N2 C6 H6 126.6 . . ? C6 C7 N1 107.8(2) . . ? C6 C7 H7 126.1 . . ? N1 C7 H7 126.1 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 111.32(19) . . ? N1 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? N1 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag OW Co1 O2 C3 -164.10(17) . . . . ? OW Co1 O2 C3 15.90(17) 2_665 . . . ? O4 Co1 O2 C3 -71.54(17) 2_665 . . . ? O4 Co1 O2 C3 108.46(17) . . . . ? O2 Co1 O2 C3 90(100) 2_665 . . . ? OW Co1 O4 C1 161.50(17) . . . . ? OW Co1 O4 C1 -18.50(17) 2_665 . . . ? O4 Co1 O4 C1 12(100) 2_665 . . . ? O2 Co1 O4 C1 -110.13(17) . . . . ? O2 Co1 O4 C1 69.87(17) 2_665 . . . ? Co1 O4 C1 O1 12.9(3) . . . . ? Co1 O4 C1 C2 -168.82(12) . . . . ? O1 C1 C2 F4 -152.75(18) . . . . ? O4 C1 C2 F4 28.7(2) . . . . ? O1 C1 C2 F3 -34.4(2) . . . . ? O4 C1 C2 F3 147.10(17) . . . . ? O1 C1 C2 C2 85.7(3) . . . 2_666 ? O4 C1 C2 C2 -92.8(3) . . . 2_666 ? Co1 O2 C3 O3 -19.6(3) . . . . ? Co1 O2 C3 C4 158.27(13) . . . . ? O3 C3 C4 F1 -140.8(2) . . . . ? O2 C3 C4 F1 41.0(2) . . . . ? O3 C3 C4 F2 -23.9(3) . . . . ? O2 C3 C4 F2 157.89(18) . . . . ? O3 C3 C4 C4 97.6(3) . . . 2_655 ? O2 C3 C4 C4 -80.7(3) . . . 2_655 ? C6 N2 C5 N1 -0.2(3) . . . . ? C8 N2 C5 N1 -179.5(2) . . . . ? C7 N1 C5 N2 0.3(3) . . . . ? C9 N1 C5 N2 -178.6(2) . . . . ? C5 N2 C6 C7 0.1(3) . . . . ? C8 N2 C6 C7 179.3(2) . . . . ? N2 C6 C7 N1 0.1(3) . . . . ? C5 N1 C7 C6 -0.3(3) . . . . ? C9 N1 C7 C6 178.6(2) . . . . ? C5 N1 C9 C10 75.3(3) . . . . ? C7 N1 C9 C10 -103.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.658 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.078