#------------------------------------------------------------------------------ #$Date: 2019-12-11 10:56:54 +0200 (Wed, 11 Dec 2019) $ #$Revision: 244980 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/64/1556488.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_1556488 loop_ _publ_author_name 'Rosca, S.-C.' 'Roueindeji, H.' 'Dorcet, V.' 'Roisnel, T.' 'Carpentier, J.-F.' 'Sarazin, Y.' _publ_section_title ; K+...Cpi and K+...F Non-Covalent Interactions in pi-Functionalized Potassium Fluoroalkoxides ; _journal_name_full Inorganics _journal_page_first 13 _journal_paper_doi 10.3390/inorganics5010013 _journal_volume 5 _journal_year 2017 _chemical_absolute_configuration ad _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C12 H16 F6 K1 N1 O1' _chemical_formula_sum 'C12 H16 F6 K N O' _chemical_formula_weight 343.36 _space_group_IT_number 114 _space_group_name_Hall 'P -4 2n' _space_group_name_H-M_alt 'P -4 21 c' _symmetry_cell_setting tetragonal _symmetry_Int_Tables_number 114 _symmetry_space_group_name_Hall 'P -4 2n' _symmetry_space_group_name_H-M 'P -4 21 c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 13.5114(14) _cell_length_b 13.5114 _cell_length_c 17.556(3) _cell_measurement_reflns_used 445 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 18.79 _cell_measurement_theta_min 2.77 _cell_measurement_wavelength 0.71073 _cell_volume 3205.0(6) _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 2012), CRYSCAL (T. Roisnel, local program) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0886 _diffrn_reflns_av_unetI/netI 0.0888 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 17470 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.02 _exptl_absorpt_coefficient_mu 0.389 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_correction_T_min 0.794 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1408 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.234 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.052 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(5) _refine_ls_extinction_coef 0.0034(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 3501 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.963 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0466 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.0942 _reflns_number_gt 2146 _reflns_number_total 3501 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; .res file for SHELXL : SR437.res ................................................................. TITL import in P -4 21 c CELL 0.71073 13.5114 13.5114 17.5560 90.000 90.000 90.000 ZERR 8.00 0.0014 0.0000 0.0030 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, Z SYMM 1/2 + X, 1/2 - Y, 1/2 - Z SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + Y, 1/2 + X, 1/2 + Z SYMM 1/2 - Y, 1/2 - X, 1/2 + Z SYMM - Y, X, - Z SYMM Y, - X, - Z SFAC C H N O F K UNIT 96 128 8 8 48 8 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.035700 EXTI 0.003445 FVAR 0.47823 K1 6 1.035444 0.135979 0.925167 11.00000 0.03384 0.02792 = 0.03137 0.00220 -0.00059 -0.00139 O1 4 0.864314 0.042442 0.925415 11.00000 0.03384 0.02856 = 0.03061 0.00110 -0.00907 -0.00043 C1 1 0.841688 0.033943 0.792253 11.00000 0.05237 0.03380 = 0.03962 0.00167 -0.01540 0.00688 F1 5 0.928359 0.078298 0.778032 11.00000 0.05138 0.04496 = 0.04637 0.00389 0.00998 -0.00281 F2 5 0.860703 -0.064770 0.789458 11.00000 0.05536 0.03700 = 0.04587 -0.00672 -0.00859 0.00566 F3 5 0.783281 0.052074 0.732228 11.00000 0.06980 0.07481 = 0.03428 -0.00554 -0.01862 0.02203 C2 1 0.799707 0.066457 0.869976 11.00000 0.03782 0.02861 = 0.03028 0.00023 -0.00989 0.00173 C3 1 0.700732 0.012043 0.883243 11.00000 0.04347 0.03329 = 0.04435 0.00621 -0.01336 -0.00292 F4 5 0.710775 -0.087328 0.883407 11.00000 0.06466 0.03373 = 0.05636 0.00536 -0.00769 -0.01454 F5 5 0.630152 0.032780 0.831964 11.00000 0.04656 0.06470 = 0.07922 0.02399 -0.03089 -0.01986 F6 5 0.663391 0.036032 0.951640 11.00000 0.05063 0.04707 = 0.05677 0.00510 0.01246 -0.00246 C4 1 0.770663 0.178564 0.865930 11.00000 0.03574 0.03031 = 0.04225 0.00001 -0.00716 0.00134 AFIX 23 H4A 2 0.731806 0.189968 0.818934 11.00000 -1.20000 H4B 2 0.727506 0.194393 0.909843 11.00000 -1.20000 AFIX 0 N5 3 0.856028 0.246826 0.866354 11.00000 0.04183 0.02872 = 0.03982 0.00444 -0.00544 -0.00547 C6 1 0.851967 0.312342 0.933038 11.00000 0.05212 0.03499 = 0.04526 -0.00032 -0.01607 -0.00032 AFIX 23 H6A 2 0.916161 0.347299 0.936956 11.00000 -1.20000 H6B 2 0.845137 0.270550 0.979057 11.00000 -1.20000 AFIX 0 C7 1 0.768839 0.390530 0.934399 11.00000 0.07347 0.03510 = 0.06095 -0.00913 -0.01764 0.01420 AFIX 23 H7A 2 0.776909 0.435875 0.890542 11.00000 -1.20000 H7B 2 0.703945 0.357162 0.929294 11.00000 -1.20000 AFIX 0 C8 1 0.770640 0.449344 1.007166 11.00000 0.11761 0.05269 = 0.09134 -0.01932 -0.01674 0.03427 AFIX 43 H8 2 0.828956 0.486188 1.017644 11.00000 -1.20000 AFIX 0 C9 1 0.700004 0.454296 1.056749 11.00000 0.18159 0.11816 = 0.09853 -0.03589 -0.01402 0.07315 AFIX 93 H9A 2 0.640293 0.418685 1.048676 11.00000 -1.20000 H9B 2 0.707836 0.493546 1.101240 11.00000 -1.20000 AFIX 0 C10 1 0.865406 0.299756 0.793106 11.00000 0.04966 0.03855 = 0.04364 0.01545 -0.00662 -0.00295 AFIX 23 H10A 2 0.807085 0.343187 0.786173 11.00000 -1.20000 H10B 2 0.865568 0.250876 0.751098 11.00000 -1.20000 AFIX 0 C11 1 0.958710 0.361993 0.788235 11.00000 0.05678 0.04754 = 0.07604 0.03436 -0.00160 -0.00495 AFIX 23 H11A 2 0.960704 0.394726 0.737807 11.00000 -1.20000 H11B 2 0.955384 0.414546 0.827446 11.00000 -1.20000 AFIX 0 C12 1 1.052026 0.305185 0.798956 11.00000 0.04994 0.05556 = 0.07167 0.02744 0.00905 -0.00881 AFIX 43 H12 2 1.061183 0.248290 0.767953 11.00000 -1.20000 AFIX 0 C13 1 1.123607 0.326894 0.847956 11.00000 0.05761 0.06609 = 0.09522 0.04087 0.00082 -0.01882 AFIX 93 H13A 2 1.117629 0.383123 0.880117 11.00000 -1.20000 H13B 2 1.180823 0.286204 0.850870 11.00000 -1.20000 HKLF 4 REM import in P -4 21 c REM R1 = 0.0466 for 2146 Fo > 4sig(Fo) and 0.1014 for all 3501 data REM 191 parameters refined using 0 restraints END WGHT 0.0348 0.0000 REM Highest difference peak 0.23, deepest hole -0.22, 1-sigma level 0.05 Q1 1 0.9636 0.2315 0.9198 11.00000 0.05 0.23 Q2 1 0.7798 -0.0382 0.9312 11.00000 0.05 0.22 Q3 1 0.9082 0.1160 0.8658 11.00000 0.05 0.21 Q4 1 1.0522 0.1316 0.9495 11.00000 0.05 0.21 Q5 1 0.8313 0.4714 0.9996 11.00000 0.05 0.20 Q6 1 0.9421 0.4360 0.8165 11.00000 0.05 0.20 Q7 1 0.7783 0.5418 0.9862 11.00000 0.05 0.19 Q8 1 0.8997 0.5152 0.9823 11.00000 0.05 0.19 Q9 1 0.6321 -0.0786 0.9462 11.00000 0.05 0.18 Q10 1 0.9316 0.2292 0.9937 11.00000 0.05 0.18 Q11 1 0.7578 0.0929 0.9876 11.00000 0.05 0.18 Q12 1 0.6003 0.3216 0.9626 11.00000 0.05 0.18 Q13 1 1.1009 0.3745 0.9279 11.00000 0.05 0.18 Q14 1 0.6852 0.0475 0.9201 11.00000 0.05 0.18 Q15 1 0.6557 0.5206 1.1661 11.00000 0.05 0.17 Q16 1 0.6286 0.4322 0.8764 11.00000 0.05 0.17 Q17 1 1.0716 0.2072 0.8773 11.00000 0.05 0.17 Q18 1 0.7699 0.1011 0.8696 11.00000 0.05 0.17 Q19 1 0.6888 0.0409 0.6940 11.00000 0.05 0.17 Q20 1 0.7688 0.0601 0.9178 11.00000 0.05 0.17 ; _cod_data_source_file Complex_3_SR437_CIFfile.cif _cod_data_source_block SR437 _cod_database_code 1556488 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' 'y+1/2, x+1/2, z+1/2' '-y+1/2, -x+1/2, z+1/2' '-y, x, -z' 'y, -x, -z' 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 K1 K 1.03544(5) 0.13598(5) 0.92517(4) 0.03104(19) Uani 1 1 d . . O1 O 0.86431(14) 0.04244(14) 0.92541(11) 0.0310(5) Uani 1 1 d . . C1 C 0.8417(3) 0.0339(3) 0.7923(2) 0.0419(9) Uani 1 1 d . . F1 F 0.92836(15) 0.07830(14) 0.77803(12) 0.0476(5) Uani 1 1 d . . F2 F 0.86070(15) -0.06477(13) 0.78946(11) 0.0461(5) Uani 1 1 d . . F3 F 0.78328(16) 0.05207(17) 0.73223(11) 0.0596(6) Uani 1 1 d . . C2 C 0.7997(2) 0.0665(2) 0.86998(19) 0.0322(8) Uani 1 1 d . . C3 C 0.7007(3) 0.0120(3) 0.8832(2) 0.0404(9) Uani 1 1 d . . F4 F 0.71078(15) -0.08733(14) 0.88341(13) 0.0516(6) Uani 1 1 d . . F5 F 0.63015(16) 0.03278(16) 0.83196(13) 0.0635(6) Uani 1 1 d . . F6 F 0.66339(14) 0.03603(15) 0.95164(12) 0.0515(6) Uani 1 1 d . . C4 C 0.7707(2) 0.1786(2) 0.8659(2) 0.0361(9) Uani 1 1 d . . H4A H 0.7318 0.19 0.8189 0.043 Uiso 1 1 calc R . H4B H 0.7275 0.1944 0.9098 0.043 Uiso 1 1 calc R . N5 N 0.8560(2) 0.24683(19) 0.86635(16) 0.0368(7) Uani 1 1 d . . C6 C 0.8520(3) 0.3123(2) 0.9330(2) 0.0441(9) Uani 1 1 d . . H6A H 0.9162 0.3473 0.937 0.053 Uiso 1 1 calc R . H6B H 0.8451 0.2705 0.9791 0.053 Uiso 1 1 calc R . C7 C 0.7688(3) 0.3905(3) 0.9344(2) 0.0565(11) Uani 1 1 d . . H7A H 0.7769 0.4359 0.8905 0.068 Uiso 1 1 calc R . H7B H 0.7039 0.3572 0.9293 0.068 Uiso 1 1 calc R . C8 C 0.7706(4) 0.4493(3) 1.0072(3) 0.0872(17) Uani 1 1 d . . H8 H 0.829 0.4862 1.0176 0.105 Uiso 1 1 calc R . C9 C 0.7000(6) 0.4543(5) 1.0567(4) 0.133(3) Uani 1 1 d . . H9A H 0.6403 0.4187 1.0487 0.159 Uiso 1 1 calc R . H9B H 0.7078 0.4935 1.1012 0.159 Uiso 1 1 calc R . C10 C 0.8654(3) 0.2998(3) 0.7931(2) 0.0440(10) Uani 1 1 d . . H10A H 0.8071 0.3432 0.7862 0.053 Uiso 1 1 calc R . H10B H 0.8656 0.2509 0.7511 0.053 Uiso 1 1 calc R . C11 C 0.9587(3) 0.3620(3) 0.7882(3) 0.0601(11) Uani 1 1 d . . H11A H 0.9607 0.3947 0.7378 0.072 Uiso 1 1 calc R . H11B H 0.9554 0.4145 0.8274 0.072 Uiso 1 1 calc R . C12 C 1.0520(3) 0.3052(3) 0.7990(3) 0.0591(12) Uani 1 1 d . . H12 H 1.0612 0.2483 0.768 0.071 Uiso 1 1 calc R . C13 C 1.1236(3) 0.3269(3) 0.8480(3) 0.0730(15) Uani 1 1 d . . H13A H 1.1176 0.3831 0.8801 0.088 Uiso 1 1 calc R . H13B H 1.1808 0.2862 0.8509 0.088 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 K1 0.0338(4) 0.0279(4) 0.0314(4) 0.0022(4) -0.0006(4) -0.0014(3) O1 0.0338(11) 0.0286(10) 0.0306(11) 0.0011(12) -0.0091(12) -0.0004(11) C1 0.052(2) 0.0338(19) 0.040(2) 0.0017(19) -0.015(2) 0.007(2) F1 0.0514(13) 0.0450(12) 0.0464(13) 0.0039(11) 0.0100(12) -0.0028(10) F2 0.0554(12) 0.0370(11) 0.0459(12) -0.0067(10) -0.0086(12) 0.0057(10) F3 0.0698(14) 0.0748(16) 0.0343(12) -0.0055(12) -0.0186(12) 0.0220(13) C2 0.0378(19) 0.0286(18) 0.0303(19) 0.0002(17) -0.0099(18) 0.0017(15) C3 0.043(2) 0.033(2) 0.044(2) 0.0062(19) -0.013(2) -0.0029(17) F4 0.0647(14) 0.0337(12) 0.0564(15) 0.0054(11) -0.0077(12) -0.0145(11) F5 0.0466(12) 0.0647(15) 0.0792(15) 0.0240(13) -0.0309(13) -0.0199(13) F6 0.0506(13) 0.0471(12) 0.0568(14) 0.0051(11) 0.0125(11) -0.0025(11) C4 0.0357(19) 0.0303(18) 0.042(2) 0.0000(18) -0.0072(18) 0.0013(16) N5 0.0418(17) 0.0287(14) 0.0398(18) 0.0044(14) -0.0054(16) -0.0055(14) C6 0.052(2) 0.0350(18) 0.045(2) -0.0003(19) -0.016(2) -0.0003(17) C7 0.073(3) 0.035(2) 0.061(3) -0.009(2) -0.018(2) 0.014(2) C8 0.118(4) 0.053(3) 0.091(4) -0.019(3) -0.017(4) 0.034(3) C9 0.182(7) 0.118(5) 0.099(5) -0.036(4) -0.014(5) 0.073(5) C10 0.050(2) 0.039(2) 0.044(2) 0.0155(19) -0.007(2) -0.0029(18) C11 0.057(2) 0.048(2) 0.076(3) 0.034(2) -0.002(3) -0.005(2) C12 0.050(3) 0.056(3) 0.072(3) 0.027(2) 0.009(3) -0.009(2) C13 0.058(3) 0.066(3) 0.095(4) 0.041(3) 0.001(3) -0.019(2) 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 0 '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 0.006 '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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1 K1 O1 91.67(7) 8_667 . O1 K1 O1 88.82(6) 8_667 2_755 O1 K1 O1 90.67(6) . 2_755 O1 K1 F2 142.70(6) 8_667 2_755 O1 K1 F2 105.32(6) . 2_755 O1 K1 F2 58.67(6) 2_755 2_755 O1 K1 N5 111.72(7) 8_667 . O1 K1 N5 62.34(7) . . O1 K1 N5 145.40(7) 2_755 . F2 K1 N5 105.58(7) 2_755 . O1 K1 F1 149.29(6) 8_667 . O1 K1 F1 57.63(6) . . O1 K1 F1 90.62(6) 2_755 . F2 K1 F1 57.06(5) 2_755 . N5 K1 F1 57.34(6) . . O1 K1 C13 114.70(11) 8_667 . O1 K1 C13 136.53(10) . . O1 K1 C13 121.99(10) 2_755 . F2 K1 C13 74.78(10) 2_755 . N5 K1 C13 75.58(10) . . F1 K1 C13 91.38(10) . . O1 K1 C12 133.82(10) 8_667 . O1 K1 C12 113.97(9) . . O1 K1 C12 126.24(9) 2_755 . F2 K1 C12 68.70(9) 2_755 . N5 K1 C12 57.70(9) . . F1 K1 C12 68.27(9) . . C13 K1 C12 24.16(10) . . O1 K1 C6 89.25(8) 8_667 . O1 K1 C6 72.54(7) . . O1 K1 C6 163.03(8) 2_755 . F2 K1 C6 127.27(7) 2_755 . N5 K1 C6 25.22(7) . . F1 K1 C6 82.51(7) . . C13 K1 C6 73.89(11) . . C12 K1 C6 65.32(10) . . O1 K1 C2 108.22(7) 8_667 . O1 K1 C2 20.33(7) . . O1 K1 C2 102.40(7) 2_755 . F2 K1 C2 97.13(7) 2_755 . N5 K1 C2 45.76(7) . . F1 K1 C2 42.22(7) . . C13 K1 C2 116.76(10) . . C12 K1 C2 93.71(9) . . C6 K1 C2 62.35(8) . . O1 K1 K1 47.37(5) 8_667 7_647 O1 K1 K1 44.31(5) . 7_647 O1 K1 K1 89.18(4) 2_755 7_647 F2 K1 K1 138.23(4) 2_755 7_647 N5 K1 K1 85.63(6) . 7_647 F1 K1 K1 101.93(4) . 7_647 C13 K1 K1 146.17(10) . 7_647 C12 K1 K1 141.98(8) . 7_647 C6 K1 K1 77.18(7) . 7_647 C2 K1 K1 61.97(6) . 7_647 O1 K1 K1 44.53(5) 8_667 8_667 O1 K1 K1 91.17(5) . 8_667 O1 K1 K1 44.30(4) 2_755 8_667 F2 K1 K1 101.14(4) 2_755 8_667 N5 K1 K1 146.32(6) . 8_667 F1 K1 K1 127.16(4) . 8_667 C13 K1 K1 132.03(9) . 8_667 C12 K1 K1 154.40(8) . 8_667 C6 K1 K1 131.24(7) . 8_667 C2 K1 K1 111.19(5) . 8_667 K1 K1 K1 60.71(2) 7_647 8_667 C2 O1 K1 136.87(19) . 7_647 C2 O1 K1 116.87(18) . . K1 O1 K1 91.16(7) 7_647 . C2 O1 K1 121.76(18) . 2_755 K1 O1 K1 88.33(6) 7_647 2_755 K1 O1 K1 89.33(6) . 2_755 F1 C1 F3 106.7(3) . . F1 C1 F2 105.5(3) . . F3 C1 F2 105.2(3) . . F1 C1 C2 111.1(3) . . F3 C1 C2 115.3(3) . . F2 C1 C2 112.4(3) . . C1 F1 K1 111.71(19) . . C1 F2 K1 112.56(18) . 2_755 O1 C2 C1 109.4(3) . . O1 C2 C3 109.7(3) . . C1 C2 C3 108.5(3) . . O1 C2 C4 115.3(3) . . C1 C2 C4 109.1(3) . . C3 C2 C4 104.5(3) . . O1 C2 K1 42.81(14) . . C1 C2 K1 89.23(19) . . C3 C2 K1 152.2(2) . . C4 C2 K1 88.90(18) . . F5 C3 F6 106.4(3) . . F5 C3 F4 106.3(3) . . F6 C3 F4 106.0(3) . . F5 C3 C2 114.5(3) . . F6 C3 C2 110.2(3) . . F4 C3 C2 112.8(3) . . N5 C4 C2 114.1(3) . . N5 C4 H4A 108.7 . . C2 C4 H4A 108.7 . . N5 C4 H4B 108.7 . . C2 C4 H4B 108.7 . . H4A C4 H4B 107.6 . . C6 N5 C10 113.9(3) . . C6 N5 C4 110.6(3) . . C10 N5 C4 111.4(3) . . C6 N5 K1 93.22(18) . . C10 N5 K1 117.9(2) . . C4 N5 K1 108.53(17) . . N5 C6 C7 116.9(3) . . N5 C6 K1 61.56(16) . . C7 C6 K1 178.5(3) . . N5 C6 H6A 108.1 . . C7 C6 H6A 108.1 . . K1 C6 H6A 72.7 . . N5 C6 H6B 108.1 . . C7 C6 H6B 108.1 . . K1 C6 H6B 72.8 . . H6A C6 H6B 107.3 . . C8 C7 C6 111.3(3) . . C8 C7 H7A 109.4 . . C6 C7 H7A 109.4 . . C8 C7 H7B 109.4 . . C6 C7 H7B 109.4 . . H7A C7 H7B 108 . . C9 C8 C7 125.9(6) . . C9 C8 H8 117 . . C7 C8 H8 117 . . C8 C9 H9A 120 . . C8 C9 H9B 120 . . H9A C9 H9B 120 . . N5 C10 C11 112.9(3) . . N5 C10 H10A 109 . . C11 C10 H10A 109 . . N5 C10 H10B 109 . . C11 C10 H10B 109 . . H10A C10 H10B 107.8 . . C12 C11 C10 114.3(3) . . C12 C11 H11A 108.7 . . C10 C11 H11A 108.7 . . C12 C11 H11B 108.7 . . C10 C11 H11B 108.7 . . H11A C11 H11B 107.6 . . C13 C12 C11 125.8(5) . . C13 C12 K1 76.1(2) . . C11 C12 K1 113.4(2) . . C13 C12 H12 117.1 . . C11 C12 H12 117.1 . . K1 C12 H12 80.1 . . C12 C13 K1 79.8(2) . . C12 C13 H13A 120 . . K1 C13 H13A 111.5 . . C12 C13 H13B 120 . . K1 C13 H13B 79.1 . . H13A C13 H13B 120 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 K1 O1 2.625(2) 8_667 K1 O1 2.635(2) . K1 O1 2.765(2) 2_755 K1 F2 2.928(2) 2_755 K1 N5 3.031(3) . K1 F1 3.062(2) . K1 C13 3.148(4) . K1 C12 3.192(4) . K1 C6 3.441(3) . K1 C2 3.459(3) . K1 K1 3.7568(12) 7_647 K1 K1 3.7568(12) 8_667 O1 C2 1.347(3) . O1 K1 2.625(2) 7_647 O1 K1 2.765(2) 2_755 C1 F1 1.339(4) . C1 F3 1.339(4) . C1 F2 1.359(4) . C1 C2 1.542(5) . F2 K1 2.928(2) 2_755 C2 C3 1.544(5) . C2 C4 1.566(4) . C3 F5 1.341(4) . C3 F6 1.342(4) . C3 F4 1.349(4) . C4 N5 1.477(4) . C4 H4A 0.99 . C4 H4B 0.99 . N5 C6 1.469(4) . N5 C10 1.477(4) . C6 C7 1.542(5) . C6 H6A 0.99 . C6 H6B 0.99 . C7 C8 1.505(6) . C7 H7A 0.99 . C7 H7B 0.99 . C8 C9 1.293(7) . C8 H8 0.95 . C9 H9A 0.95 . C9 H9B 0.95 . C10 C11 1.518(5) . C10 H10A 0.99 . C10 H10B 0.99 . C11 C12 1.488(5) . C11 H11A 0.99 . C11 H11B 0.99 . C12 C13 1.327(6) . C12 H12 0.95 . C13 H13A 0.95 . C13 H13B 0.95 . 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 O1 K1 O1 C2 145.2(2) 8_667 . . . O1 K1 O1 C2 -125.92(19) 2_755 . . . F2 K1 O1 C2 -68.3(2) 2_755 . . . N5 K1 O1 C2 31.50(19) . . . . F1 K1 O1 C2 -35.60(19) . . . . C13 K1 O1 C2 15.6(3) . . . . C12 K1 O1 C2 4.8(2) . . . . C6 K1 O1 C2 56.6(2) . . . . K1 K1 O1 C2 145.9(2) 7_647 . . . K1 K1 O1 C2 -170.22(19) 8_667 . . . O1 K1 O1 K1 -0.70(7) 8_667 . . 7_647 O1 K1 O1 K1 88.14(7) 2_755 . . 7_647 F2 K1 O1 K1 145.72(6) 2_755 . . 7_647 N5 K1 O1 K1 -114.45(8) . . . 7_647 F1 K1 O1 K1 178.45(8) . . . 7_647 C13 K1 O1 K1 -130.39(15) . . . 7_647 C12 K1 O1 K1 -141.15(10) . . . 7_647 C6 K1 O1 K1 -89.39(8) . . . 7_647 C2 K1 O1 K1 -145.9(2) . . . 7_647 K1 K1 O1 K1 43.84(5) 8_667 . . 7_647 O1 K1 O1 K1 -89.02(7) 8_667 . . 2_755 O1 K1 O1 K1 -0.18(9) 2_755 . . 2_755 F2 K1 O1 K1 57.41(7) 2_755 . . 2_755 N5 K1 O1 K1 157.24(9) . . . 2_755 F1 K1 O1 K1 90.13(7) . . . 2_755 C13 K1 O1 K1 141.29(14) . . . 2_755 C12 K1 O1 K1 130.53(10) . . . 2_755 C6 K1 O1 K1 -177.71(9) . . . 2_755 C2 K1 O1 K1 125.7(2) . . . 2_755 K1 K1 O1 K1 -88.32(6) 7_647 . . 2_755 K1 K1 O1 K1 -44.48(6) 8_667 . . 2_755 F3 C1 F1 K1 152.54(19) . . . . F2 C1 F1 K1 -95.9(2) . . . . C2 C1 F1 K1 26.1(3) . . . . O1 K1 F1 C1 3.3(2) 8_667 . . . O1 K1 F1 C1 1.69(18) . . . . O1 K1 F1 C1 92.09(19) 2_755 . . . F2 K1 F1 C1 143.3(2) 2_755 . . . N5 K1 F1 C1 -74.03(19) . . . . C13 K1 F1 C1 -145.9(2) . . . . C12 K1 F1 C1 -138.7(2) . . . . C6 K1 F1 C1 -72.3(2) . . . . C2 K1 F1 C1 -15.82(19) . . . . K1 K1 F1 C1 2.80(19) 7_647 . . . K1 K1 F1 C1 64.9(2) 8_667 . . . F1 C1 F2 K1 75.5(3) . . . 2_755 F3 C1 F2 K1 -171.93(18) . . . 2_755 C2 C1 F2 K1 -45.7(3) . . . 2_755 K1 O1 C2 C1 -168.7(2) 7_647 . . . K1 O1 C2 C1 66.3(3) . . . . K1 O1 C2 C1 -41.0(3) 2_755 . . . K1 O1 C2 C3 -49.8(4) 7_647 . . . K1 O1 C2 C3 -174.79(19) . . . . K1 O1 C2 C3 77.9(3) 2_755 . . . K1 O1 C2 C4 67.9(4) 7_647 . . . K1 O1 C2 C4 -57.1(3) . . . . K1 O1 C2 C4 -164.5(2) 2_755 . . . K1 O1 C2 K1 125.0(3) 7_647 . . . K1 O1 C2 K1 -107.3(2) 2_755 . . . F1 C1 C2 O1 -59.7(3) . . . . F3 C1 C2 O1 178.8(3) . . . . F2 C1 C2 O1 58.2(4) . . . . F1 C1 C2 C3 -179.4(3) . . . . F3 C1 C2 C3 59.1(4) . . . . F2 C1 C2 C3 -61.5(4) . . . . F1 C1 C2 C4 67.3(3) . . . . F3 C1 C2 C4 -54.1(4) . . . . F2 C1 C2 C4 -174.7(3) . . . . F1 C1 C2 K1 -21.2(2) . . . . F3 C1 C2 K1 -142.7(3) . . . . F2 C1 C2 K1 96.7(3) . . . . O1 K1 C2 O1 -36.9(2) 8_667 . . . O1 K1 C2 O1 56.01(19) 2_755 . . . F2 K1 C2 O1 115.4(2) 2_755 . . . N5 K1 C2 O1 -139.8(2) . . . . F1 K1 C2 O1 133.0(2) . . . . C13 K1 C2 O1 -168.1(2) . . . . C12 K1 C2 O1 -175.6(2) . . . . C6 K1 C2 O1 -116.0(2) . . . . K1 K1 C2 O1 -26.31(18) 7_647 . . . K1 K1 C2 O1 10.5(2) 8_667 . . . O1 K1 C2 C1 -157.12(17) 8_667 . . . O1 K1 C2 C1 -120.3(3) . . . . O1 K1 C2 C1 -64.24(19) 2_755 . . . F2 K1 C2 C1 -4.85(18) 2_755 . . . N5 K1 C2 C1 100.0(2) . . . . F1 K1 C2 C1 12.71(15) . . . . C13 K1 C2 C1 71.7(2) . . . . C12 K1 C2 C1 64.13(19) . . . . C6 K1 C2 C1 123.7(2) . . . . K1 K1 C2 C1 -146.56(19) 7_647 . . . K1 K1 C2 C1 -109.76(17) 8_667 . . . O1 K1 C2 C3 -26.3(5) 8_667 . . . O1 K1 C2 C3 10.6(4) . . . . O1 K1 C2 C3 66.6(5) 2_755 . . . F2 K1 C2 C3 126.0(5) 2_755 . . . N5 K1 C2 C3 -129.2(5) . . . . F1 K1 C2 C3 143.5(5) . . . . C13 K1 C2 C3 -157.5(5) . . . . C12 K1 C2 C3 -165.1(5) . . . . C6 K1 C2 C3 -105.5(5) . . . . K1 K1 C2 C3 -15.8(5) 7_647 . . . K1 K1 C2 C3 21.0(5) 8_667 . . . O1 K1 C2 C4 93.73(19) 8_667 . . . O1 K1 C2 C4 130.6(3) . . . . O1 K1 C2 C4 -173.39(18) 2_755 . . . F2 K1 C2 C4 -113.99(19) 2_755 . . . N5 K1 C2 C4 -9.16(18) . . . . F1 K1 C2 C4 -96.4(2) . . . . C13 K1 C2 C4 -37.5(2) . . . . C12 K1 C2 C4 -45.0(2) . . . . C6 K1 C2 C4 14.57(18) . . . . K1 K1 C2 C4 104.29(19) 7_647 . . . K1 K1 C2 C4 141.09(18) 8_667 . . . O1 C2 C3 F5 178.5(3) . . . . C1 C2 C3 F5 -62.1(4) . . . . C4 C2 C3 F5 54.2(4) . . . . K1 C2 C3 F5 170.9(3) . . . . O1 C2 C3 F6 58.5(3) . . . . C1 C2 C3 F6 178.0(3) . . . . C4 C2 C3 F6 -65.7(3) . . . . K1 C2 C3 F6 50.9(6) . . . . O1 C2 C3 F4 -59.8(4) . . . . C1 C2 C3 F4 59.7(4) . . . . C4 C2 C3 F4 176.0(3) . . . . K1 C2 C3 F4 -67.4(6) . . . . O1 C2 C4 N5 49.7(4) . . . . C1 C2 C4 N5 -73.9(4) . . . . C3 C2 C4 N5 170.2(3) . . . . K1 C2 C4 N5 14.9(3) . . . . C2 C4 N5 C6 -118.9(3) . . . . C2 C4 N5 C10 113.4(3) . . . . C2 C4 N5 K1 -18.0(3) . . . . O1 K1 N5 C6 28.5(2) 8_667 . . . O1 K1 N5 C6 108.5(2) . . . . O1 K1 N5 C6 151.08(18) 2_755 . . . F2 K1 N5 C6 -152.05(18) 2_755 . . . F1 K1 N5 C6 176.1(2) . . . . C13 K1 N5 C6 -82.7(2) . . . . C12 K1 N5 C6 -100.5(2) . . . . C2 K1 N5 C6 123.2(2) . . . . K1 K1 N5 C6 68.90(18) 7_647 . . . K1 K1 N5 C6 66.7(2) 8_667 . . . O1 K1 N5 C10 147.8(2) 8_667 . . . O1 K1 N5 C10 -132.2(2) . . . . O1 K1 N5 C10 -89.6(2) 2_755 . . . F2 K1 N5 C10 -32.8(2) 2_755 . . . F1 K1 N5 C10 -64.7(2) . . . . C13 K1 N5 C10 36.6(2) . . . . C12 K1 N5 C10 18.7(2) . . . . C6 K1 N5 C10 119.3(3) . . . . C2 K1 N5 C10 -117.5(2) . . . . K1 K1 N5 C10 -171.8(2) 7_647 . . . K1 K1 N5 C10 -174.04(18) 8_667 . . . O1 K1 N5 C4 -84.4(2) 8_667 . . . O1 K1 N5 C4 -4.42(19) . . . . O1 K1 N5 C4 38.1(3) 2_755 . . . F2 K1 N5 C4 95.0(2) 2_755 . . . F1 K1 N5 C4 63.1(2) . . . . C13 K1 N5 C4 164.3(2) . . . . C12 K1 N5 C4 146.5(3) . . . . C6 K1 N5 C4 -112.9(3) . . . . C2 K1 N5 C4 10.26(19) . . . . K1 K1 N5 C4 -44.0(2) 7_647 . . . K1 K1 N5 C4 -46.3(3) 8_667 . . . C10 N5 C6 C7 57.4(4) . . . . C4 N5 C6 C7 -69.0(4) . . . . K1 N5 C6 C7 179.9(3) . . . . C10 N5 C6 K1 -122.5(3) . . . . C4 N5 C6 K1 111.2(2) . . . . O1 K1 C6 N5 -153.68(18) 8_667 . . . O1 K1 C6 N5 -61.68(18) . . . . O1 K1 C6 N5 -70.2(4) 2_755 . . . F2 K1 C6 N5 34.6(2) 2_755 . . . F1 K1 C6 N5 -3.33(18) . . . . C13 K1 C6 N5 90.3(2) . . . . C12 K1 C6 N5 66.1(2) . . . . C2 K1 C6 N5 -42.58(17) . . . . K1 K1 C6 N5 -107.44(18) 7_647 . . . K1 K1 C6 N5 -137.36(16) 8_667 . . . O1 K1 C6 C7 -158(10) 8_667 . . . O1 K1 C6 C7 -66(10) . . . . O1 K1 C6 C7 -74(10) 2_755 . . . F2 K1 C6 C7 31(10) 2_755 . . . N5 K1 C6 C7 -4(10) . . . . F1 K1 C6 C7 -7(10) . . . . C13 K1 C6 C7 86(10) . . . . C12 K1 C6 C7 62(10) . . . . C2 K1 C6 C7 -47(10) . . . . K1 K1 C6 C7 -111(10) 7_647 . . . K1 K1 C6 C7 -141(10) 8_667 . . . N5 C6 C7 C8 177.5(4) . . . . K1 C6 C7 C8 -18E1(10) . . . . C6 C7 C8 C9 -119.4(6) . . . . C6 N5 C10 C11 60.4(4) . . . . C4 N5 C10 C11 -173.6(3) . . . . K1 N5 C10 C11 -47.2(4) . . . . N5 C10 C11 C12 57.9(5) . . . . C10 C11 C12 C13 -127.6(4) . . . . C10 C11 C12 K1 -38.2(5) . . . . O1 K1 C12 C13 43.6(3) 8_667 . . . O1 K1 C12 C13 161.7(3) . . . . O1 K1 C12 C13 -88.3(3) 2_755 . . . F2 K1 C12 C13 -100.4(3) 2_755 . . . N5 K1 C12 C13 133.6(3) . . . . F1 K1 C12 C13 -162.2(3) . . . . C6 K1 C12 C13 106.2(3) . . . . C2 K1 C12 C13 163.4(3) . . . . K1 K1 C12 C13 116.4(3) 7_647 . . . K1 K1 C12 C13 -29.9(4) 8_667 . . . O1 K1 C12 C11 -79.8(3) 8_667 . . . O1 K1 C12 C11 38.3(4) . . . . O1 K1 C12 C11 148.3(3) 2_755 . . . F2 K1 C12 C11 136.2(3) 2_755 . . . N5 K1 C12 C11 10.2(3) . . . . F1 K1 C12 C11 74.4(3) . . . . C13 K1 C12 C11 -123.4(5) . . . . C6 K1 C12 C11 -17.2(3) . . . . C2 K1 C12 C11 40.0(3) . . . . K1 K1 C12 C11 -7.0(4) 7_647 . . . K1 K1 C12 C11 -153.3(2) 8_667 . . . C11 C12 C13 K1 109.1(4) . . . . O1 K1 C13 C12 -146.8(3) 8_667 . . . O1 K1 C13 C12 -24.6(4) . . . . O1 K1 C13 C12 108.1(3) 2_755 . . . F2 K1 C13 C12 71.7(3) 2_755 . . . N5 K1 C13 C12 -39.2(3) . . . . F1 K1 C13 C12 16.5(3) . . . . C6 K1 C13 C12 -65.3(3) . . . . C2 K1 C13 C12 -18.7(3) . . . . K1 K1 C13 C12 -97.5(3) 7_647 . . . K1 K1 C13 C12 163.1(2) 8_667 . . .