#------------------------------------------------------------------------------ #$Date: 2021-09-15 21:28:02 +0300 (Wed, 15 Sep 2021) $ #$Revision: 269154 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/46/1564658.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1564658 loop_ _publ_author_name 'Hoffmann, Kurt F.' 'Wiesner, Anja' 'M\"uller, Carsten' 'Steinhauer, Simon' 'Beckers, Helmut' 'Kazim, Muhammad' 'Pitts, Cody Ross' 'Lectka, Thomas' 'Riedel, Sebastian' _publ_section_title ; Structural proof of a [C--F--C]+ fluoronium cation ; _journal_issue 1 _journal_name_full 'Nature Communications' _journal_page_first 5275 _journal_paper_doi 10.1038/s41467-021-25592-6 _journal_volume 12 _journal_year 2021 _chemical_formula_moiety 'C14 H14 F6 O3 Sb, F11 Sb2, 3(Cl F O2 S)' _chemical_formula_sum 'C14 H14 Cl3 F20 O9 S3 Sb3' _chemical_formula_weight 1274.03 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _cell_angle_alpha 90 _cell_angle_beta 92.583(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.4633(5) _cell_length_b 24.9968(12) _cell_length_c 14.8197(8) _cell_measurement_reflns_used 9472 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.291 _cell_measurement_theta_min 2.633 _cell_volume 3502.1(3) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)' _computing_data_reduction 'SAINT V8.38A (Bruker, 2018)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_unetI/netI 0.0120 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 134176 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.327 _diffrn_reflns_theta_min 2.132 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.853 _exptl_absorpt_correction_T_max 0.6035 _exptl_absorpt_correction_T_min 0.4512 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1297 before and 0.0517 after correction. The Ratio of minimum to maximum transmission is 0.7476. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier . _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.416 _exptl_crystal_description block _exptl_crystal_F_000 2408 _exptl_crystal_size_max 0.399 _exptl_crystal_size_mid 0.239 _exptl_crystal_size_min 0.153 _refine_diff_density_max 1.811 _refine_diff_density_min -0.754 _refine_diff_density_rms 0.093 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 510 _refine_ls_number_reflns 8717 _refine_ls_number_restraints 18 _refine_ls_restrained_S_all 1.161 _refine_ls_R_factor_all 0.0247 _refine_ls_R_factor_gt 0.0233 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0141P)^2^+9.3363P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.0535 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 8353 _reflns_number_total 8717 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 1.cif _cod_data_source_block mu35_a _cod_database_code 1564658 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.669 _shelx_estimated_absorpt_t_min 0.396 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(F3S) \\sim Ueq, Uanis(O6S) \\sim Ueq, Uanis(F3AS) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.002 3. Others Sof(F3AS)=Sof(S3AS)=Sof(O6AS)=Sof(O5AS)=Sof(Cl3A)=1-FVAR(1) Sof(Cl3S)=Sof(S3S)=Sof(F3S)=Sof(O5S)=Sof(O6S)=FVAR(1) 4.a Ternary CH refined with riding coordinates: C11(H11), C6(H6), C1(H1), C2(H2), C8(H8), C3(H3) 4.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B), C4(H4A,H4B), C10(H10A,H10B), C5(H5A,H5B) ; _shelx_res_file ; TITL mu35_a.res in P2(1)/c mu35_a.res created by SHELXL-2018/3 at 19:24:06 on 08-Dec-2020 REM Old TITL mu35 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.123, Rweak 0.006, Alpha 0.041, Orientation as input REM Formula found by SHELXT: C16 Cl3A F3AS O17 S3AS Sb3 CELL 0.71073 9.4633 24.9968 14.8197 90 92.583 90 ZERR 4 0.0005 0.0012 0.0008 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl F O S Sb UNIT 56 56 12 80 36 12 12 ISOR 0.01 0.002 F3S O6S F3AS L.S. 40 PLAN 5 SIZE 0.153 0.239 0.399 TEMP -173.15 CONF BOND $H LIST 6 MORE -1 fmap 2 acta OMIT 1 1 0 REM REM REM WGHT 0.014100 9.336300 FVAR 0.18137 0.58648 SB1 7 -0.139132 0.408355 0.454407 11.00000 0.01178 0.01533 = 0.01352 0.00046 0.00333 0.00029 F1 4 0.403824 0.425202 0.144858 11.00000 0.01723 0.01838 = 0.01181 -0.00045 0.00399 0.00032 F5 4 -0.247161 0.466108 0.412038 11.00000 0.01997 0.02287 = 0.03550 0.00844 0.00864 0.00874 F2 4 -0.269470 0.386240 0.537043 11.00000 0.02411 0.02571 = 0.02777 0.00540 0.01325 -0.00052 F6 4 -0.219647 0.366254 0.362809 11.00000 0.02028 0.02824 = 0.02529 -0.00632 -0.00066 -0.00608 F3 4 -0.011706 0.353768 0.484433 11.00000 0.02038 0.02573 = 0.02950 0.01023 0.00400 0.00694 F4 4 -0.048475 0.452998 0.539439 11.00000 0.03001 0.03435 = 0.01812 -0.00992 0.00608 -0.01073 O1 5 0.004280 0.429897 0.356879 11.00000 0.01133 0.01918 = 0.01313 0.00138 0.00194 0.00016 O2 5 0.206487 0.435064 0.440075 11.00000 0.01176 0.02189 = 0.01030 -0.00091 0.00061 0.00015 O3 5 0.438086 0.441051 0.489730 11.00000 0.01673 0.02991 = 0.01356 -0.00122 -0.00380 -0.00002 C11 1 0.443914 0.483413 0.281852 11.00000 0.01186 0.01778 = 0.01314 -0.00012 -0.00038 -0.00237 AFIX 13 H11 2 0.549557 0.484708 0.282274 11.00000 -1.20000 AFIX 0 C9 1 0.218741 0.531926 0.270617 11.00000 0.01765 0.01507 = 0.01632 -0.00075 0.00264 0.00197 AFIX 23 H9A 2 0.146977 0.531650 0.317201 11.00000 -1.20000 H9B 2 0.200240 0.562661 0.229639 11.00000 -1.20000 AFIX 0 C4 1 0.385265 0.331279 0.341026 11.00000 0.01765 0.01802 = 0.01700 0.00259 0.00150 0.00352 AFIX 23 H4A 2 0.385039 0.336178 0.407309 11.00000 -1.20000 H4B 2 0.438522 0.298343 0.327655 11.00000 -1.20000 AFIX 0 C10 1 0.371241 0.534708 0.314861 11.00000 0.01926 0.01717 = 0.01704 -0.00234 0.00085 -0.00171 AFIX 23 H10A 2 0.421346 0.567061 0.294781 11.00000 -1.20000 H10B 2 0.368707 0.535156 0.381567 11.00000 -1.20000 AFIX 0 C5 1 0.230502 0.328521 0.298744 11.00000 0.01589 0.01510 = 0.01649 0.00202 0.00245 -0.00068 AFIX 23 H5A 2 0.213487 0.294187 0.266775 11.00000 -1.20000 H5B 2 0.160305 0.332534 0.345831 11.00000 -1.20000 AFIX 0 C13 1 0.135022 0.432220 0.362418 11.00000 0.01267 0.01252 = 0.01059 0.00090 0.00047 0.00092 C7 1 0.226794 0.430371 0.282859 11.00000 0.00944 0.01379 = 0.00901 0.00022 0.00038 0.00038 C6 1 0.222529 0.376062 0.232011 11.00000 0.01136 0.01509 = 0.01098 -0.00131 0.00080 -0.00064 AFIX 13 H6 2 0.148854 0.373013 0.181746 11.00000 -1.20000 AFIX 0 C1 1 0.369533 0.480140 0.189168 11.00000 0.01525 0.01285 = 0.01462 -0.00119 0.00189 0.00014 AFIX 13 H1 2 0.390154 0.511403 0.149766 11.00000 -1.20000 AFIX 0 C2 1 0.374343 0.373838 0.203886 11.00000 0.01621 0.01318 = 0.01296 0.00129 0.00147 0.00051 AFIX 13 H2 2 0.398281 0.339588 0.173227 11.00000 -1.20000 AFIX 0 C8 1 0.217142 0.478746 0.217521 11.00000 0.01334 0.01593 = 0.01030 0.00138 0.00076 0.00084 AFIX 13 H8 2 0.143643 0.475937 0.167110 11.00000 -1.20000 AFIX 0 C3 1 0.449974 0.380535 0.294931 11.00000 0.01281 0.01681 = 0.01309 0.00000 0.00018 0.00264 AFIX 13 H3 2 0.555599 0.381066 0.294440 11.00000 -1.20000 AFIX 0 C12 1 0.380344 0.433150 0.326035 11.00000 0.00985 0.01663 = 0.01095 -0.00094 0.00004 0.00063 C019 1 0.361617 0.437091 0.426070 11.00000 0.01300 0.01621 = 0.01439 -0.00008 0.00137 0.00109 SB3 7 0.794570 0.460384 0.087254 11.00000 0.01202 0.02092 = 0.01409 0.00214 0.00006 -0.00099 SB2 7 0.624300 0.344340 -0.064549 11.00000 0.01694 0.01985 = 0.01396 -0.00034 0.00094 -0.00161 F8 4 0.470934 0.341608 0.009265 11.00000 0.02095 0.03799 = 0.02504 -0.00595 0.00738 -0.00680 F9 4 0.549168 0.405576 -0.118221 11.00000 0.04118 0.02533 = 0.03595 0.00756 0.00030 0.00739 F16 4 0.728017 0.434874 0.194792 11.00000 0.03888 0.04371 = 0.02016 0.00351 0.01280 -0.00567 F17 4 0.957164 0.419828 0.103546 11.00000 0.01891 0.02852 = 0.03957 0.00010 -0.00117 0.00526 F12 4 0.707076 0.393276 0.033889 11.00000 0.03617 0.04745 = 0.03044 -0.01066 -0.00214 -0.01973 F13 4 0.878450 0.520298 0.139992 11.00000 0.03940 0.02362 = 0.05077 -0.01173 0.00368 -0.00757 F11 4 0.711533 0.289939 0.001886 11.00000 0.04380 0.04510 = 0.03153 0.01380 0.00213 0.01589 F10 4 0.789440 0.357189 -0.123885 11.00000 0.02691 0.04694 = 0.03352 0.00390 0.01489 -0.00381 F7 4 0.547793 0.298755 -0.151649 11.00000 0.04420 0.03331 = 0.02622 -0.01286 0.00200 -0.00921 F14 4 0.844817 0.476721 -0.028913 11.00000 0.03645 0.06716 = 0.02009 0.01860 -0.00085 -0.01527 F15 4 0.621666 0.493174 0.063764 11.00000 0.01846 0.05248 = 0.07797 0.02518 0.00159 0.01232 CL1S 3 0.866598 0.867590 0.564267 11.00000 0.04104 0.03012 = 0.05438 0.00026 -0.00037 -0.00807 S1S 6 0.837500 0.794264 0.518240 11.00000 0.02233 0.02454 = 0.02650 0.00980 0.00121 0.00189 F1S 4 0.990353 0.774645 0.526473 11.00000 0.02918 0.05602 = 0.06547 0.00685 -0.00655 0.01717 O1S 5 0.799398 0.796230 0.425647 11.00000 0.03802 0.03748 = 0.02475 0.00958 0.00586 0.00932 O2S 5 0.759459 0.765305 0.579893 11.00000 0.04889 0.03551 = 0.03315 0.01658 0.00361 -0.00860 CL2S 3 0.205320 0.793739 0.844561 11.00000 0.07513 0.02315 = 0.03177 -0.00604 0.00574 0.01137 S2S 6 0.203916 0.723104 0.785522 11.00000 0.02525 0.01853 = 0.02144 0.00025 0.00452 0.00163 F2S 4 0.172423 0.741915 0.687979 11.00000 0.05231 0.03029 = 0.02365 0.00272 -0.00423 0.00082 O3S 5 0.342155 0.702834 0.789939 11.00000 0.02480 0.03404 = 0.02945 -0.00676 0.00343 0.00341 O4S 5 0.087319 0.693215 0.811396 11.00000 0.02864 0.04135 = 0.04518 0.00704 0.00994 -0.00498 PART 1 CL3S 3 0.220823 0.414707 0.680176 21.00000 0.05261 0.02545 = 0.03242 -0.01110 0.01185 -0.00308 S3S 6 0.256344 0.339213 0.651390 21.00000 0.05450 0.02990 = 0.01760 0.00259 -0.00940 -0.00508 F3S 4 0.146862 0.309915 0.693610 21.00000 0.09949 0.09295 = 0.09368 0.00225 0.01409 -0.00972 O5S 5 0.280803 0.333141 0.560250 21.00000 0.04211 0.02688 = 0.02198 -0.00081 0.01511 0.00732 O6S 5 0.385025 0.333832 0.712316 21.00000 0.07222 0.07967 = 0.07029 0.00457 -0.01219 0.00808 PART 2 F3AS 4 0.450274 0.343573 0.671824 -21.00000 0.06093 0.06502 = 0.06780 0.00632 -0.00717 0.00083 S3AS 6 0.296335 0.339625 0.659992 -21.00000 0.07998 0.05237 = 0.06291 0.02350 -0.04035 -0.02596 O6AS 5 0.238231 0.302265 0.714818 -21.00000 0.12626 0.03379 = 0.02874 0.01433 0.00419 -0.03012 O5AS 5 0.267877 0.336295 0.567235 -21.00000 0.11651 0.10734 = 0.05955 0.02593 -0.04622 -0.03150 CL3A 3 0.236061 0.405856 0.693743 -21.00000 0.18542 HKLF 4 REM mu35_a.res in P2(1)/c REM wR2 = 0.0535, GooF = S = 1.149, Restrained GooF = 1.161 for all data REM R1 = 0.0233 for 8353 Fo > 4sig(Fo) and 0.0247 for all 8717 data REM 510 parameters refined using 18 restraints END WGHT 0.0150 9.9501 REM Highest difference peak 1.811, deepest hole -0.754, 1-sigma level 0.093 Q1 1 0.4500 0.3104 0.6264 11.00000 0.05 1.81 Q2 1 0.6785 0.4195 0.0022 11.00000 0.05 0.98 Q3 1 0.3353 0.3878 0.7366 11.00000 0.05 0.91 Q4 1 0.1214 0.7858 0.8549 11.00000 0.05 0.87 Q5 1 0.7406 0.3208 0.0181 11.00000 0.05 0.74 ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb -0.13913(2) 0.40836(2) 0.45441(2) 0.01346(4) Uani 1 1 d . . . . . F1 F 0.40382(15) 0.42520(6) 0.14486(9) 0.0157(3) Uani 1 1 d . . . . . F5 F -0.24716(17) 0.46611(7) 0.41204(12) 0.0259(4) Uani 1 1 d . . . . . F2 F -0.26947(18) 0.38624(7) 0.53704(12) 0.0255(4) Uani 1 1 d . . . . . F6 F -0.21965(17) 0.36625(7) 0.36281(11) 0.0247(3) Uani 1 1 d . . . . . F3 F -0.01171(17) 0.35377(7) 0.48443(12) 0.0251(3) Uani 1 1 d . . . . . F4 F -0.04847(19) 0.45300(7) 0.53944(11) 0.0273(4) Uani 1 1 d . . . . . O1 O 0.00428(18) 0.42990(7) 0.35688(11) 0.0145(3) Uani 1 1 d . . . . . O2 O 0.20649(18) 0.43506(7) 0.44007(11) 0.0146(3) Uani 1 1 d . . . . . O3 O 0.43809(19) 0.44105(8) 0.48973(12) 0.0202(4) Uani 1 1 d . . . . . C11 C 0.4439(3) 0.48341(10) 0.28185(16) 0.0143(4) Uani 1 1 d . . . . . H11 H 0.549557 0.484708 0.282274 0.017 Uiso 1 1 calc R U . . . C9 C 0.2187(3) 0.53193(10) 0.27062(17) 0.0163(5) Uani 1 1 d . . . . . H9A H 0.146977 0.531650 0.317201 0.020 Uiso 1 1 calc R U . . . H9B H 0.200240 0.562661 0.229639 0.020 Uiso 1 1 calc R U . . . C4 C 0.3853(3) 0.33128(10) 0.34103(17) 0.0175(5) Uani 1 1 d . . . . . H4A H 0.385039 0.336178 0.407309 0.021 Uiso 1 1 calc R U . . . H4B H 0.438522 0.298343 0.327655 0.021 Uiso 1 1 calc R U . . . C10 C 0.3712(3) 0.53471(10) 0.31486(17) 0.0178(5) Uani 1 1 d . . . . . H10A H 0.421346 0.567061 0.294781 0.021 Uiso 1 1 calc R U . . . H10B H 0.368707 0.535156 0.381567 0.021 Uiso 1 1 calc R U . . . C5 C 0.2305(3) 0.32852(10) 0.29874(17) 0.0158(5) Uani 1 1 d . . . . . H5A H 0.213487 0.294187 0.266775 0.019 Uiso 1 1 calc R U . . . H5B H 0.160305 0.332534 0.345831 0.019 Uiso 1 1 calc R U . . . C13 C 0.1350(2) 0.43222(9) 0.36242(15) 0.0119(4) Uani 1 1 d . . . . . C7 C 0.2268(2) 0.43037(9) 0.28286(15) 0.0107(4) Uani 1 1 d . . . . . C6 C 0.2225(2) 0.37606(9) 0.23201(16) 0.0125(4) Uani 1 1 d . . . . . H6 H 0.148854 0.373013 0.181746 0.015 Uiso 1 1 calc R U . . . C1 C 0.3695(3) 0.48014(10) 0.18917(16) 0.0142(4) Uani 1 1 d . . . . . H1 H 0.390154 0.511403 0.149766 0.017 Uiso 1 1 calc R U . . . C2 C 0.3743(3) 0.37384(10) 0.20389(16) 0.0141(4) Uani 1 1 d . . . . . H2 H 0.398281 0.339588 0.173227 0.017 Uiso 1 1 calc R U . . . C8 C 0.2171(2) 0.47875(10) 0.21752(16) 0.0132(4) Uani 1 1 d . . . . . H8 H 0.143643 0.475937 0.167110 0.016 Uiso 1 1 calc R U . . . C3 C 0.4500(3) 0.38054(10) 0.29493(16) 0.0142(4) Uani 1 1 d . . . . . H3 H 0.555599 0.381066 0.294440 0.017 Uiso 1 1 calc R U . . . C12 C 0.3803(2) 0.43315(10) 0.32604(16) 0.0125(4) Uani 1 1 d . . . . . C019 C 0.3616(3) 0.43709(10) 0.42607(16) 0.0145(4) Uani 1 1 d . . . . . Sb3 Sb 0.79457(2) 0.46038(2) 0.08725(2) 0.01569(4) Uani 1 1 d . . . . . Sb2 Sb 0.62430(2) 0.34434(2) -0.06455(2) 0.01691(4) Uani 1 1 d . . . . . F8 F 0.47093(18) 0.34161(7) 0.00927(12) 0.0278(4) Uani 1 1 d . . . . . F9 F 0.5492(2) 0.40558(7) -0.11822(13) 0.0342(4) Uani 1 1 d . . . . . F16 F 0.7280(2) 0.43487(8) 0.19479(12) 0.0339(4) Uani 1 1 d . . . . . F17 F 0.95716(18) 0.41983(7) 0.10355(13) 0.0291(4) Uani 1 1 d . . . . . F12 F 0.7071(2) 0.39328(9) 0.03389(13) 0.0381(5) Uani 1 1 d . . . . . F13 F 0.8784(2) 0.52030(7) 0.13999(15) 0.0379(5) Uani 1 1 d . . . . . F11 F 0.7115(2) 0.28994(9) 0.00189(13) 0.0401(5) Uani 1 1 d . . . . . F10 F 0.7894(2) 0.35719(8) -0.12388(13) 0.0354(4) Uani 1 1 d . . . . . F7 F 0.5478(2) 0.29876(8) -0.15165(12) 0.0346(4) Uani 1 1 d . . . . . F14 F 0.8448(2) 0.47672(10) -0.02891(12) 0.0413(5) Uani 1 1 d . . . . . F15 F 0.6217(2) 0.49317(9) 0.06376(18) 0.0497(6) Uani 1 1 d . . . . . Cl1S Cl 0.86660(10) 0.86759(3) 0.56427(7) 0.0419(2) Uani 1 1 d . . . . . S1S S 0.83750(8) 0.79426(3) 0.51824(5) 0.02445(14) Uani 1 1 d . . . . . F1S F 0.9904(2) 0.77464(10) 0.52647(17) 0.0505(6) Uani 1 1 d . . . . . O1S O 0.7994(3) 0.79623(10) 0.42565(15) 0.0333(5) Uani 1 1 d . . . . . O2S O 0.7595(3) 0.76531(10) 0.57989(16) 0.0391(6) Uani 1 1 d . . . . . Cl2S Cl 0.20532(12) 0.79374(3) 0.84456(6) 0.0432(2) Uani 1 1 d . . . . . S2S S 0.20392(7) 0.72310(3) 0.78552(5) 0.02164(13) Uani 1 1 d . . . . . F2S F 0.1724(2) 0.74192(8) 0.68798(12) 0.0356(4) Uani 1 1 d . . . . . O3S O 0.3422(2) 0.70283(9) 0.78994(15) 0.0294(5) Uani 1 1 d . . . . . O4S O 0.0873(3) 0.69321(10) 0.81140(18) 0.0381(6) Uani 1 1 d . . . . . Cl3S Cl 0.2208(2) 0.41471(7) 0.68018(12) 0.0365(7) Uani 0.586(8) 1 d . . P A 1 S3S S 0.2563(5) 0.33921(16) 0.6514(2) 0.0343(7) Uani 0.586(8) 1 d . . P A 1 F3S F 0.1469(9) 0.3099(3) 0.6936(6) 0.095(2) Uani 0.586(8) 1 d . U P A 1 O5S O 0.2808(10) 0.3331(3) 0.5602(6) 0.0299(18) Uani 0.586(8) 1 d . . P A 1 O6S O 0.3850(8) 0.3338(3) 0.7123(5) 0.075(2) Uani 0.586(8) 1 d . U P A 1 F3AS F 0.4503(8) 0.3436(3) 0.6718(6) 0.065(2) Uani 0.414(8) 1 d . U P A 2 S3AS S 0.2963(8) 0.3396(3) 0.6600(5) 0.066(2) Uani 0.414(8) 1 d . . P A 2 O6AS O 0.2382(14) 0.3023(3) 0.7148(5) 0.063(3) Uani 0.414(8) 1 d . . P A 2 O5AS O 0.268(2) 0.3363(9) 0.5672(13) 0.096(7) Uani 0.414(8) 1 d . . P A 2 Cl3A Cl 0.2361(13) 0.4059(5) 0.6937(8) 0.185(5) Uiso 0.414(8) 1 d . . P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.01178(7) 0.01533(8) 0.01352(7) 0.00046(6) 0.00333(5) 0.00029(6) F1 0.0172(7) 0.0184(7) 0.0118(6) -0.0004(5) 0.0040(5) 0.0003(6) F5 0.0200(8) 0.0229(8) 0.0355(9) 0.0084(7) 0.0086(7) 0.0087(6) F2 0.0241(8) 0.0257(8) 0.0278(9) 0.0054(7) 0.0132(7) -0.0005(7) F6 0.0203(8) 0.0282(9) 0.0253(8) -0.0063(7) -0.0007(6) -0.0061(7) F3 0.0204(8) 0.0257(8) 0.0295(9) 0.0102(7) 0.0040(7) 0.0069(6) F4 0.0300(9) 0.0344(9) 0.0181(8) -0.0099(7) 0.0061(7) -0.0107(7) O1 0.0113(8) 0.0192(8) 0.0131(8) 0.0014(6) 0.0019(6) 0.0002(6) O2 0.0118(8) 0.0219(9) 0.0103(8) -0.0009(6) 0.0006(6) 0.0002(7) O3 0.0167(9) 0.0299(10) 0.0136(8) -0.0012(7) -0.0038(7) 0.0000(7) C11 0.0119(10) 0.0178(11) 0.0131(11) -0.0001(9) -0.0004(8) -0.0024(9) C9 0.0177(11) 0.0151(11) 0.0163(11) -0.0007(9) 0.0026(9) 0.0020(9) C4 0.0176(12) 0.0180(12) 0.0170(11) 0.0026(9) 0.0015(9) 0.0035(9) C10 0.0193(12) 0.0172(12) 0.0170(11) -0.0023(9) 0.0008(9) -0.0017(9) C5 0.0159(11) 0.0151(11) 0.0165(11) 0.0020(9) 0.0025(9) -0.0007(9) C13 0.0127(10) 0.0125(10) 0.0106(10) 0.0009(8) 0.0005(8) 0.0009(8) C7 0.0094(10) 0.0138(10) 0.0090(10) 0.0002(8) 0.0004(8) 0.0004(8) C6 0.0114(10) 0.0151(11) 0.0110(10) -0.0013(8) 0.0008(8) -0.0006(8) C1 0.0153(11) 0.0129(11) 0.0146(11) -0.0012(8) 0.0019(9) 0.0001(9) C2 0.0162(11) 0.0132(11) 0.0130(11) 0.0013(8) 0.0015(9) 0.0005(9) C8 0.0133(10) 0.0159(11) 0.0103(10) 0.0014(8) 0.0008(8) 0.0008(9) C3 0.0128(10) 0.0168(11) 0.0131(11) 0.0000(9) 0.0002(8) 0.0026(9) C12 0.0098(10) 0.0166(11) 0.0110(10) -0.0009(8) 0.0000(8) 0.0006(8) C019 0.0130(11) 0.0162(11) 0.0144(11) -0.0001(9) 0.0014(9) 0.0011(9) Sb3 0.01202(7) 0.02092(8) 0.01409(8) 0.00214(6) 0.00006(6) -0.00099(6) Sb2 0.01694(8) 0.01985(8) 0.01396(8) -0.00034(6) 0.00094(6) -0.00161(6) F8 0.0209(8) 0.0380(10) 0.0250(8) -0.0060(7) 0.0074(7) -0.0068(7) F9 0.0412(11) 0.0253(9) 0.0359(10) 0.0076(8) 0.0003(8) 0.0074(8) F16 0.0389(10) 0.0437(11) 0.0202(8) 0.0035(8) 0.0128(8) -0.0057(9) F17 0.0189(8) 0.0285(9) 0.0396(10) 0.0001(8) -0.0012(7) 0.0053(7) F12 0.0362(10) 0.0475(12) 0.0304(10) -0.0107(9) -0.0021(8) -0.0197(9) F13 0.0394(11) 0.0236(9) 0.0508(12) -0.0117(8) 0.0037(9) -0.0076(8) F11 0.0438(11) 0.0451(12) 0.0315(10) 0.0138(9) 0.0021(9) 0.0159(9) F10 0.0269(9) 0.0469(11) 0.0335(10) 0.0039(9) 0.0149(8) -0.0038(8) F7 0.0442(11) 0.0333(10) 0.0262(9) -0.0129(8) 0.0020(8) -0.0092(8) F14 0.0364(11) 0.0672(14) 0.0201(9) 0.0186(9) -0.0009(8) -0.0153(10) F15 0.0185(9) 0.0525(13) 0.0780(17) 0.0252(12) 0.0016(10) 0.0123(9) Cl1S 0.0410(5) 0.0301(4) 0.0544(5) 0.0003(4) -0.0004(4) -0.0081(3) S1S 0.0223(3) 0.0245(3) 0.0265(3) 0.0098(3) 0.0012(3) 0.0019(3) F1S 0.0292(11) 0.0560(14) 0.0655(15) 0.0068(12) -0.0065(10) 0.0172(10) O1S 0.0380(13) 0.0375(13) 0.0248(11) 0.0096(9) 0.0059(9) 0.0093(10) O2S 0.0489(15) 0.0355(13) 0.0331(13) 0.0166(10) 0.0036(11) -0.0086(11) Cl2S 0.0751(6) 0.0231(4) 0.0318(4) -0.0060(3) 0.0057(4) 0.0114(4) S2S 0.0253(3) 0.0185(3) 0.0214(3) 0.0003(2) 0.0045(3) 0.0016(2) F2S 0.0523(12) 0.0303(10) 0.0236(9) 0.0027(7) -0.0042(8) 0.0008(9) O3S 0.0248(10) 0.0340(12) 0.0295(11) -0.0068(9) 0.0034(9) 0.0034(9) O4S 0.0286(12) 0.0414(14) 0.0452(14) 0.0070(11) 0.0099(10) -0.0050(10) Cl3S 0.0526(10) 0.0254(9) 0.0324(9) -0.0111(5) 0.0118(6) -0.0031(6) S3S 0.0545(19) 0.0299(10) 0.0176(10) 0.0026(7) -0.0094(11) -0.0051(11) F3S 0.099(3) 0.093(3) 0.094(3) 0.0022(18) 0.0141(19) -0.0097(19) O5S 0.042(4) 0.027(3) 0.022(4) -0.001(2) 0.015(3) 0.007(3) O6S 0.072(3) 0.080(3) 0.070(3) 0.0046(18) -0.0122(18) 0.0081(18) F3AS 0.061(3) 0.065(3) 0.068(3) 0.0063(18) -0.0072(18) 0.0008(18) S3AS 0.080(4) 0.052(2) 0.063(3) 0.0235(18) -0.040(2) -0.026(2) O6AS 0.126(9) 0.034(4) 0.029(3) 0.014(3) 0.004(4) -0.030(5) O5AS 0.117(15) 0.107(14) 0.060(11) 0.026(9) -0.046(9) -0.031(10) 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' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 '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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 4.00 1.00 0.0870 1.00 -4.00 -1.00 0.0130 -2.00 4.00 -1.00 0.1590 0.00 -5.00 -4.00 0.1190 0.00 4.00 3.00 0.1190 2.00 -5.00 0.00 0.0700 1.00 -5.00 -2.00 0.0150 4.00 5.00 -3.00 0.0500 -4.00 -5.00 3.00 0.0750 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 F5 Sb1 F3 171.48(7) . . F5 Sb1 F4 89.59(8) . . F5 Sb1 O1 86.05(7) . . F2 Sb1 F5 94.71(7) . . F2 Sb1 F3 93.81(7) . . F2 Sb1 F4 91.80(8) . . F2 Sb1 O1 176.97(7) . . F6 Sb1 F5 89.54(8) . . F6 Sb1 F2 92.89(8) . . F6 Sb1 F3 89.96(8) . . F6 Sb1 F4 175.28(7) . . F6 Sb1 O1 84.17(7) . . F3 Sb1 F4 90.22(8) . . F3 Sb1 O1 85.45(7) . . F4 Sb1 O1 91.13(7) . . C1 F1 C2 115.77(15) . . C13 O1 Sb1 129.97(16) . . C13 O2 C019 110.59(18) . . C10 C11 H11 115.5 . . C10 C11 C12 110.61(19) . . C1 C11 H11 115.5 . . C1 C11 C10 97.84(19) . . C1 C11 C12 99.53(19) . . C12 C11 H11 115.5 . . H9A C9 H9B 109.0 . . C10 C9 H9A 111.0 . . C10 C9 H9B 111.0 . . C8 C9 H9A 111.0 . . C8 C9 H9B 111.0 . . C8 C9 C10 103.90(19) . . H4A C4 H4B 109.0 . . C5 C4 H4A 111.0 . . C5 C4 H4B 111.0 . . C3 C4 H4A 111.0 . . C3 C4 H4B 111.0 . . C3 C4 C5 103.86(19) . . C11 C10 C9 104.27(19) . . C11 C10 H10A 110.9 . . C11 C10 H10B 110.9 . . C9 C10 H10A 110.9 . . C9 C10 H10B 110.9 . . H10A C10 H10B 108.9 . . C4 C5 H5A 111.0 . . C4 C5 H5B 111.0 . . H5A C5 H5B 109.0 . . C6 C5 C4 103.86(19) . . C6 C5 H5A 111.0 . . C6 C5 H5B 111.0 . . O1 C13 O2 122.4(2) . . O1 C13 C7 124.1(2) . . O2 C13 C7 113.5(2) . . C13 C7 C6 113.97(19) . . C13 C7 C8 116.64(19) . . C13 C7 C12 103.77(18) . . C6 C7 C12 103.95(18) . . C8 C7 C6 112.31(18) . . C8 C7 C12 104.41(18) . . C5 C6 C7 111.24(19) . . C5 C6 H6 115.5 . . C7 C6 H6 115.5 . . C2 C6 C5 97.37(18) . . C2 C6 C7 99.29(18) . . C2 C6 H6 115.5 . . F1 C1 H1 113.1 . . C11 C1 F1 109.34(18) . . C11 C1 H1 113.1 . . C11 C1 C8 99.10(19) . . C8 C1 F1 108.27(18) . . C8 C1 H1 113.1 . . F1 C2 H2 113.2 . . C6 C2 F1 108.34(18) . . C6 C2 H2 113.2 . . C3 C2 F1 108.40(18) . . C3 C2 C6 99.64(19) . . C3 C2 H2 113.2 . . C9 C8 C7 110.76(19) . . C9 C8 H8 115.6 . . C7 C8 H8 115.6 . . C1 C8 C9 97.67(19) . . C1 C8 C7 99.25(18) . . C1 C8 H8 115.6 . . C4 C3 H3 115.4 . . C4 C3 C12 111.20(19) . . C2 C3 C4 97.20(19) . . C2 C3 H3 115.4 . . C2 C3 C12 99.75(19) . . C12 C3 H3 115.4 . . C11 C12 C7 103.56(18) . . C3 C12 C11 112.56(19) . . C3 C12 C7 103.91(19) . . C019 C12 C11 115.4(2) . . C019 C12 C7 104.94(18) . . C019 C12 C3 114.8(2) . . O2 C019 C12 107.16(19) . . O3 C019 O2 117.9(2) . . O3 C019 C12 134.9(2) . . F16 Sb3 F12 84.35(9) . . F17 Sb3 F16 90.69(9) . . F17 Sb3 F12 85.39(9) . . F17 Sb3 F13 92.86(9) . . F17 Sb3 F14 89.73(9) . . F13 Sb3 F16 94.08(9) . . F13 Sb3 F12 177.63(9) . . F13 Sb3 F14 95.21(10) . . F14 Sb3 F16 170.66(9) . . F14 Sb3 F12 86.38(9) . . F15 Sb3 F16 88.98(10) . . F15 Sb3 F17 172.56(10) . . F15 Sb3 F12 87.17(10) . . F15 Sb3 F13 94.58(10) . . F15 Sb3 F14 89.39(10) . . F8 Sb2 F12 83.43(8) . . F9 Sb2 F8 89.33(9) . . F9 Sb2 F12 86.50(9) . . F9 Sb2 F10 88.20(9) . . F11 Sb2 F8 90.08(9) . . F11 Sb2 F9 171.46(10) . . F11 Sb2 F12 84.96(10) . . F11 Sb2 F10 90.82(9) . . F10 Sb2 F8 169.28(8) . . F10 Sb2 F12 86.01(9) . . F7 Sb2 F8 95.56(8) . . F7 Sb2 F9 94.53(9) . . F7 Sb2 F12 178.55(9) . . F7 Sb2 F11 94.01(10) . . F7 Sb2 F10 95.03(9) . . Sb3 F12 Sb2 156.91(12) . . F1S S1S Cl1S 98.86(11) . . O1S S1S Cl1S 109.36(11) . . O1S S1S F1S 106.86(14) . . O2S S1S Cl1S 108.92(12) . . O2S S1S F1S 107.88(15) . . O2S S1S O1S 122.38(16) . . F2S S2S Cl2S 98.09(8) . . O3S S2S Cl2S 108.40(11) . . O3S S2S F2S 107.20(13) . . O4S S2S Cl2S 110.25(12) . . O4S S2S F2S 107.40(14) . . O4S S2S O3S 122.66(15) . . F3S S3S Cl3S 105.1(4) . . F3S S3S O6S 106.0(5) . . O5S S3S Cl3S 110.7(4) . . O5S S3S F3S 121.6(6) . . O5S S3S O6S 114.3(6) . . O6S S3S Cl3S 95.6(3) . . F3AS S3AS Cl3A 103.1(6) . . O6AS S3AS F3AS 113.5(7) . . O6AS S3AS O5AS 118.7(11) . . O6AS S3AS Cl3A 108.5(7) . . O5AS S3AS F3AS 105.7(11) . . O5AS S3AS Cl3A 106.0(10) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Sb1 F5 1.8616(16) . Sb1 F2 1.8609(15) . Sb1 F6 1.8541(16) . Sb1 F3 1.8616(16) . Sb1 F4 1.8633(16) . Sb1 O1 2.0971(17) . F1 C1 1.563(3) . F1 C2 1.585(3) . O1 C13 1.238(3) . O2 C13 1.310(3) . O2 C019 1.493(3) . O3 C019 1.167(3) . C11 H11 1.0000 . C11 C10 1.545(3) . C11 C1 1.517(3) . C11 C12 1.551(3) . C9 H9A 0.9900 . C9 H9B 0.9900 . C9 C10 1.560(4) . C9 C8 1.544(3) . C4 H4A 0.9900 . C4 H4B 0.9900 . C4 C5 1.568(4) . C4 C3 1.548(3) . C10 H10A 0.9900 . C10 H10B 0.9900 . C5 H5A 0.9900 . C5 H5B 0.9900 . C5 C6 1.546(3) . C13 C7 1.496(3) . C7 C6 1.552(3) . C7 C8 1.549(3) . C7 C12 1.563(3) . C6 H6 1.0000 . C6 C2 1.515(3) . C1 H1 1.0000 . C1 C8 1.521(3) . C2 H2 1.0000 . C2 C3 1.508(3) . C8 H8 1.0000 . C3 H3 1.0000 . C3 C12 1.550(3) . C12 C019 1.504(3) . Sb3 F16 1.8530(17) . Sb3 F17 1.8493(17) . Sb3 F12 2.0164(19) . Sb3 F13 1.8515(18) . Sb3 F14 1.8521(18) . Sb3 F15 1.8490(19) . Sb2 F8 1.8576(16) . Sb2 F9 1.8521(18) . Sb2 F12 2.0335(18) . Sb2 F11 1.8511(19) . Sb2 F10 1.8554(17) . Sb2 F7 1.8451(17) . Cl1S S1S 1.9707(12) . S1S F1S 1.527(2) . S1S O1S 1.404(2) . S1S O2S 1.402(2) . Cl2S S2S 1.9703(11) . S2S F2S 1.5365(19) . S2S O3S 1.402(2) . S2S O4S 1.400(2) . Cl3S S3S 1.967(4) . S3S F3S 1.435(8) . S3S O5S 1.389(8) . S3S O6S 1.489(7) . F3AS S3AS 1.463(10) . S3AS O6AS 1.369(10) . S3AS O5AS 1.39(2) . S3AS Cl3A 1.828(13) . 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 Sb1 O1 C13 O2 -19.2(3) . . . . Sb1 O1 C13 C7 158.82(17) . . . . F1 C1 C8 C9 171.71(17) . . . . F1 C1 C8 C7 59.1(2) . . . . F1 C2 C3 C4 171.56(17) . . . . F1 C2 C3 C12 58.5(2) . . . . O1 C13 C7 C6 -66.2(3) . . . . O1 C13 C7 C8 67.2(3) . . . . O1 C13 C7 C12 -178.6(2) . . . . O2 C13 C7 C6 111.9(2) . . . . O2 C13 C7 C8 -114.6(2) . . . . O2 C13 C7 C12 -0.4(3) . . . . C11 C1 C8 C9 57.7(2) . . . . C11 C1 C8 C7 -54.9(2) . . . . C11 C12 C019 O2 114.8(2) . . . . C11 C12 C019 O3 -65.3(4) . . . . C4 C5 C6 C7 -69.1(2) . . . . C4 C5 C6 C2 33.9(2) . . . . C4 C3 C12 C11 179.39(19) . . . . C4 C3 C12 C7 -69.2(2) . . . . C4 C3 C12 C019 44.8(3) . . . . C10 C11 C1 F1 -170.22(17) . . . . C10 C11 C1 C8 -57.1(2) . . . . C10 C11 C12 C7 68.4(2) . . . . C10 C11 C12 C3 180.0(2) . . . . C10 C11 C12 C019 -45.7(3) . . . . C10 C9 C8 C7 68.0(2) . . . . C10 C9 C8 C1 -35.0(2) . . . . C5 C4 C3 C2 -35.0(2) . . . . C5 C4 C3 C12 68.5(2) . . . . C5 C6 C2 F1 -171.31(17) . . . . C5 C6 C2 C3 -58.1(2) . . . . C13 O2 C019 O3 178.1(2) . . . . C13 O2 C019 C12 -1.9(3) . . . . C13 C7 C6 C5 -43.8(3) . . . . C13 C7 C6 C2 -145.6(2) . . . . C13 C7 C8 C9 44.7(3) . . . . C13 C7 C8 C1 146.6(2) . . . . C13 C7 C12 C11 -122.11(19) . . . . C13 C7 C12 C3 120.10(19) . . . . C13 C7 C12 C019 -0.8(2) . . . . C7 C6 C2 F1 -58.3(2) . . . . C7 C6 C2 C3 54.9(2) . . . . C7 C12 C019 O2 1.6(2) . . . . C7 C12 C019 O3 -178.5(3) . . . . C6 C7 C8 C9 178.88(19) . . . . C6 C7 C8 C1 -79.2(2) . . . . C6 C7 C12 C11 118.43(19) . . . . C6 C7 C12 C3 0.6(2) . . . . C6 C7 C12 C019 -120.2(2) . . . . C6 C2 C3 C4 58.4(2) . . . . C6 C2 C3 C12 -54.6(2) . . . . C1 F1 C2 C6 54.0(2) . . . . C1 F1 C2 C3 -53.2(2) . . . . C1 C11 C10 C9 33.6(2) . . . . C1 C11 C12 C7 -33.8(2) . . . . C1 C11 C12 C3 77.8(2) . . . . C1 C11 C12 C019 -147.8(2) . . . . C2 F1 C1 C11 52.8(2) . . . . C2 F1 C1 C8 -54.2(2) . . . . C2 C3 C12 C11 -78.9(2) . . . . C2 C3 C12 C7 32.5(2) . . . . C2 C3 C12 C019 146.5(2) . . . . C8 C9 C10 C11 0.9(2) . . . . C8 C7 C6 C5 -179.32(19) . . . . C8 C7 C6 C2 79.0(2) . . . . C8 C7 C12 C11 0.5(2) . . . . C8 C7 C12 C3 -117.24(19) . . . . C8 C7 C12 C019 121.9(2) . . . . C3 C4 C5 C6 0.6(2) . . . . C3 C12 C019 O2 -111.8(2) . . . . C3 C12 C019 O3 68.1(4) . . . . C12 C11 C10 C9 -69.7(2) . . . . C12 C11 C1 F1 -57.7(2) . . . . C12 C11 C1 C8 55.5(2) . . . . C12 C7 C6 C5 68.4(2) . . . . C12 C7 C6 C2 -33.3(2) . . . . C12 C7 C8 C9 -69.1(2) . . . . C12 C7 C8 C1 32.8(2) . . . . C019 O2 C13 O1 179.7(2) . . . . C019 O2 C13 C7 1.5(3) . . . .