#------------------------------------------------------------------------------ #$Date: 2017-06-27 04:13:01 +0300 (Tue, 27 Jun 2017) $ #$Revision: 198148 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/63/1546384.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_1546384 loop_ _publ_author_name 'Landmann, Johannes' 'Hennig, Philipp T.' 'Ignat'ev, Nikolai' 'Finze, Maik' _publ_section_title ; Borylation of Fluorinated Arenes with the Boron-centred Nucleophile B(CN)32− -- a Unique Entry to Aryltricyanoborates ; _journal_name_full 'Chem. Sci.' _journal_paper_doi 10.1039/C7SC02249B _journal_year 2017 _chemical_formula_moiety 'C12 H8 B F3 K N3 O2' _chemical_formula_sum 'C12 H8 B F3 K N3 O2' _chemical_formula_weight 333.12 _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-05-09 deposited with the CCDC. 2017-06-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.205(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.9371(9) _cell_length_b 7.5514(5) _cell_length_c 14.3323(10) _cell_measurement_reflns_used 7338 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.75 _cell_measurement_theta_min 2.85 _cell_volume 1397.98(17) _computing_cell_refinement 'Saint+ ver. V8.34A (Bruker AXS)' _computing_data_collection 'APEX2 ver. 2014.9 (Bruker AXS)' _computing_data_reduction 'Saint+ ver. V8.34A (Bruker AXS)' _computing_molecular_graphics 'ShelXLe (Huebschle et all, 2011)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD area detector (Apex2)' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker X8-APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0751 _diffrn_reflns_av_unetI/netI 0.0484 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 17851 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 2.847 _diffrn_source 'rotating-anode (Nonius FR-591)' _exptl_absorpt_coefficient_mu 0.423 _exptl_absorpt_correction_T_max 0.745430 _exptl_absorpt_correction_T_min 0.659870 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SadAbs 2014/5 (Bruker AXS)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.583 _exptl_crystal_description plate _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.920 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.087 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2857 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0500 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+2.7374P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1167 _refine_ls_wR_factor_ref 0.1260 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2516 _reflns_number_total 2857 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7sc02249b2.cif _cod_data_source_block JL096_JL_K2N2EtOAc _cod_database_code 1546384 _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_res_file ; twin5.res created by SHELXL-2014/7 TITL twin4_a.res in P2(1)/c REM Old TITL twin4 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.136, Rweak 0.016, Alpha 0.038, Orientation as input REM Formula found by SHELXT: C13 O5 F3 K CELL 0.71073 12.9371 7.5514 14.3323 90.000 93.205 90.000 ZERR 4.000 0.0009 0.0005 0.0010 0.000 0.003 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H O F K N B UNIT 48 32 8 12 4 12 4 TEMP -173 L.S. 10 BOND $H OMIT 1 0 0 SHEL 999 0.8 ACTA 52 LIST 4 FMAP 2 PLAN 20 WGHT 0.037700 2.737400 BASF 0.50445 FVAR 0.81831 K1 5 0.497747 -0.007792 0.321866 11.00000 0.01685 0.01676 = 0.01732 0.00118 -0.00145 -0.00079 N1 6 0.571807 0.347241 0.362790 11.00000 0.02069 0.02506 = 0.01883 -0.00160 0.00274 -0.00215 O1 3 0.339474 0.209064 0.247404 11.00000 0.02468 0.04054 = 0.03209 -0.00555 -0.00465 0.01266 C1 1 0.616276 0.417830 0.422615 11.00000 0.01289 0.01760 = 0.01631 0.00028 0.00549 0.00171 N2 6 0.611098 0.349878 0.664895 11.00000 0.02061 0.02248 = 0.02132 0.00266 0.00272 0.00188 O2 3 0.174018 0.116739 0.241733 11.00000 0.02756 0.03922 = 0.02920 0.00719 0.00087 0.01477 C2 1 0.638635 0.422869 0.600949 11.00000 0.00994 0.01680 = 0.02008 -0.00484 -0.00230 0.00380 N3 6 0.607638 0.858021 0.499167 11.00000 0.02158 0.02436 = 0.02877 0.00090 0.00386 0.00213 C3 1 0.638261 0.716841 0.505140 11.00000 0.01275 0.02027 = 0.01607 -0.00050 0.00223 -0.00157 B4 7 0.676382 0.515049 0.508734 11.00000 0.00913 0.02035 = 0.01698 0.00013 0.00104 0.00160 C12 1 0.800975 0.489792 0.502856 11.00000 0.01455 0.03386 = 0.01162 0.00278 0.00216 0.00370 C13 1 0.838296 0.317688 0.475461 11.00000 0.01489 0.02779 = 0.02601 0.00752 0.00462 0.00395 F13 4 0.772134 0.187043 0.463183 11.00000 0.02315 0.02280 = 0.05741 -0.00493 -0.00333 0.00067 C14 1 0.940635 0.285358 0.466364 11.00000 0.02404 0.01997 = 0.02534 -0.00437 0.00220 0.00155 F14 4 0.968431 0.124134 0.436673 11.00000 0.02446 0.01575 = 0.05468 -0.01334 -0.00844 0.00511 C15 1 1.015560 0.415285 0.484810 11.00000 0.03117 0.01584 = 0.01230 0.00163 0.00247 -0.00143 C21 1 0.204239 0.401287 0.188096 11.00000 0.02894 0.03318 = 0.03004 -0.00116 -0.00236 0.01069 AFIX 137 H00A 2 0.194707 0.388851 0.120097 11.00000 -1.50000 H00B 2 0.251596 0.499812 0.203100 11.00000 -1.50000 H00C 2 0.137232 0.424909 0.214272 11.00000 -1.50000 AFIX 0 C22 1 0.248288 0.235683 0.228577 11.00000 0.02786 0.03820 = 0.01586 -0.00619 -0.00219 0.01231 C23 1 0.206570 -0.050536 0.283883 11.00000 0.03301 0.03995 = 0.02915 0.00721 0.00612 0.01678 AFIX 23 H00G 2 0.243534 -0.030108 0.345294 11.00000 -1.20000 H00H 2 0.253472 -0.114058 0.243071 11.00000 -1.20000 AFIX 0 C24 1 0.110003 -0.156428 0.295444 11.00000 0.03786 0.04132 = 0.02958 0.00212 0.00835 0.01235 AFIX 137 H00D 2 0.072235 -0.169740 0.234651 11.00000 -1.50000 H00E 2 0.066128 -0.095098 0.338702 11.00000 -1.50000 H00F 2 0.128565 -0.273616 0.320531 11.00000 -1.50000 AFIX 0 C11 1 0.875007 0.612233 0.522363 11.00000 0.01866 0.02594 = 0.02131 -0.00165 -0.00092 0.00143 F11 4 0.845477 0.772510 0.550344 11.00000 0.02008 0.03354 = 0.03426 -0.00980 -0.00146 -0.00271 REM ##### HKLF 5 REM twin4_a.res in P2(1)/c REM R1 = 0.0500 for 2516 Fo > 4sig(Fo) and 0.0599 for all 2857 data REM 202 parameters refined using 0 restraints END WGHT 0.0381 2.7236 REM Highest difference peak 0.920, deepest hole -0.478, 1-sigma level 0.087 Q1 1 0.7968 0.8398 0.5833 11.00000 0.05 0.92 Q2 1 0.8667 0.4299 0.4794 11.00000 0.05 0.66 Q3 1 1.0390 0.2878 0.4579 11.00000 0.05 0.66 Q4 1 0.8197 0.2616 0.4250 11.00000 0.05 0.47 Q5 1 1.0167 0.1475 0.3862 11.00000 0.05 0.38 Q6 1 0.7365 0.5059 0.5125 11.00000 0.05 0.31 Q7 1 0.9547 0.3987 0.4694 11.00000 0.05 0.31 Q8 1 0.8943 0.3043 0.5046 11.00000 0.05 0.30 Q9 1 0.5374 0.9668 0.5116 11.00000 0.05 0.30 Q10 1 0.8765 0.3130 0.4479 11.00000 0.05 0.29 Q11 1 0.4994 0.3379 0.3126 11.00000 0.05 0.27 Q12 1 0.2844 0.7021 0.1813 11.00000 0.05 0.27 Q13 1 0.1981 0.3256 0.0539 11.00000 0.05 0.26 Q14 1 0.9813 0.0580 0.4997 11.00000 0.05 0.26 Q15 1 0.9625 0.4715 0.4969 11.00000 0.05 0.26 Q16 1 0.6762 0.3956 0.6379 11.00000 0.05 0.24 Q17 1 0.2804 -0.0865 0.4480 11.00000 0.05 0.24 Q18 1 0.3246 0.2056 0.3386 11.00000 0.05 0.24 Q19 1 0.1664 0.0533 0.1668 11.00000 0.05 0.23 Q20 1 0.2604 0.0603 0.4365 11.00000 0.05 0.23 ; _shelx_res_checksum 57880 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 K1 K 0.49775(7) -0.00779(10) 0.32187(5) 0.01707(18) Uani 1 1 d . . N1 N 0.5718(2) 0.3472(4) 0.3628(2) 0.0215(7) Uani 1 1 d . . O1 O 0.3395(2) 0.2091(4) 0.2474(2) 0.0327(7) Uani 1 1 d . . C1 C 0.6163(3) 0.4178(5) 0.4226(3) 0.0154(7) Uani 1 1 d . . N2 N 0.6111(2) 0.3499(4) 0.6649(2) 0.0214(7) Uani 1 1 d . . O2 O 0.1740(2) 0.1167(4) 0.2417(2) 0.0320(7) Uani 1 1 d . . C2 C 0.6386(3) 0.4229(5) 0.6009(3) 0.0157(7) Uani 1 1 d . . N3 N 0.6076(2) 0.8580(4) 0.4992(3) 0.0248(7) Uani 1 1 d . . C3 C 0.6383(2) 0.7168(4) 0.5051(3) 0.0163(7) Uani 1 1 d . . B4 B 0.6764(3) 0.5150(5) 0.5087(3) 0.0155(7) Uani 1 1 d . . C12 C 0.8010(3) 0.4898(5) 0.5029(3) 0.0200(8) Uani 1 1 d . . C13 C 0.8383(3) 0.3177(5) 0.4755(3) 0.0228(8) Uani 1 1 d . . F13 F 0.77213(17) 0.1870(3) 0.4632(2) 0.0347(6) Uani 1 1 d . . C14 C 0.9406(3) 0.2854(5) 0.4664(3) 0.0231(8) Uani 1 1 d . . F14 F 0.96843(18) 0.1241(3) 0.4367(2) 0.0320(6) Uani 1 1 d . . C15 C 1.0156(3) 0.4153(5) 0.4848(3) 0.0197(8) Uani 1 1 d . . C21 C 0.2042(3) 0.4013(6) 0.1881(3) 0.0309(10) Uani 1 1 d . . H00A H 0.1947 0.3889 0.1201 0.046 Uiso 1 1 calc R U H00B H 0.2516 0.4998 0.2031 0.046 Uiso 1 1 calc R U H00C H 0.1372 0.4249 0.2143 0.046 Uiso 1 1 calc R U C22 C 0.2483(3) 0.2357(6) 0.2286(3) 0.0274(9) Uani 1 1 d . . C23 C 0.2066(3) -0.0505(6) 0.2839(3) 0.0339(10) Uani 1 1 d . . H00G H 0.2435 -0.0301 0.3453 0.041 Uiso 1 1 calc R U H00H H 0.2535 -0.1141 0.2431 0.041 Uiso 1 1 calc R U C24 C 0.1100(3) -0.1564(6) 0.2954(3) 0.0360(11) Uani 1 1 d . . H00D H 0.0722 -0.1697 0.2347 0.054 Uiso 1 1 calc R U H00E H 0.0661 -0.0951 0.3387 0.054 Uiso 1 1 calc R U H00F H 0.1286 -0.2736 0.3205 0.054 Uiso 1 1 calc R U C11 C 0.8750(3) 0.6122(5) 0.5224(3) 0.0220(8) Uani 1 1 d . . F11 F 0.84548(16) 0.7725(3) 0.55034(17) 0.0294(6) Uani 1 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.0168(3) 0.0168(3) 0.0173(3) 0.0012(3) -0.0014(4) -0.0008(3) N1 0.0207(15) 0.0251(17) 0.0188(16) -0.0016(14) 0.0027(13) -0.0022(14) O1 0.0247(14) 0.0405(19) 0.0321(17) -0.0056(15) -0.0047(13) 0.0127(13) C1 0.0129(16) 0.0176(18) 0.0163(17) 0.0003(15) 0.0055(14) 0.0017(14) N2 0.0206(15) 0.0225(16) 0.0213(17) 0.0027(14) 0.0027(13) 0.0019(13) O2 0.0276(15) 0.0392(18) 0.0292(16) 0.0072(14) 0.0009(13) 0.0148(13) C2 0.0099(15) 0.0168(18) 0.0201(18) -0.0048(15) -0.0023(14) 0.0038(13) N3 0.0216(14) 0.0244(16) 0.0288(17) 0.0009(16) 0.0039(15) 0.0021(13) C3 0.0127(14) 0.0203(18) 0.0161(16) -0.0005(16) 0.0022(15) -0.0016(13) B4 0.0091(14) 0.0203(18) 0.0170(17) 0.0001(17) 0.0010(18) 0.0016(14) C12 0.0145(15) 0.034(2) 0.0116(17) 0.0028(16) 0.0022(14) 0.0037(15) C13 0.0149(16) 0.0278(19) 0.026(2) 0.0075(18) 0.0046(17) 0.0040(15) F13 0.0231(11) 0.0228(12) 0.0574(16) -0.0049(13) -0.0033(12) 0.0007(9) C14 0.0240(18) 0.0200(18) 0.025(2) -0.0044(17) 0.0022(17) 0.0016(15) F14 0.0245(11) 0.0158(11) 0.0547(16) -0.0133(11) -0.0084(11) 0.0051(9) C15 0.031(2) 0.0158(17) 0.0123(18) 0.0016(16) 0.0025(16) -0.0014(14) C21 0.029(2) 0.033(2) 0.030(2) -0.0012(18) -0.0024(18) 0.0107(18) C22 0.0279(19) 0.038(2) 0.0159(18) -0.0062(17) -0.0022(17) 0.012(2) C23 0.033(2) 0.040(3) 0.029(2) 0.007(2) 0.0061(19) 0.017(2) C24 0.038(2) 0.041(3) 0.030(2) 0.002(2) 0.008(2) 0.012(2) C11 0.0187(17) 0.0259(19) 0.0213(19) -0.0017(18) -0.0009(16) 0.0014(14) F11 0.0201(11) 0.0335(13) 0.0343(13) -0.0098(11) -0.0015(10) -0.0027(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' 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' K K 0.2009 0.2494 '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' B B 0.0013 0.0007 '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 N1 76.19(9) . . O1 K1 N2 101.29(10) . 3_656 N1 K1 N2 161.86(9) . 3_656 O1 K1 N1 72.22(9) . 2_645 N1 K1 N1 127.20(9) . 2_645 N2 K1 N1 67.13(9) 3_656 2_645 O1 K1 N2 81.88(9) . 4_565 N1 K1 N2 67.29(9) . 4_565 N2 K1 N2 130.59(8) 3_656 4_565 N1 K1 N2 67.24(9) 2_645 4_565 O1 K1 N3 145.22(9) . 1_545 N1 K1 N3 90.31(9) . 1_545 N2 K1 N3 81.72(9) 3_656 1_545 N1 K1 N3 137.30(9) 2_645 1_545 N2 K1 N3 122.55(9) 4_565 1_545 O1 K1 N3 76.17(9) . 3_666 N1 K1 N3 70.08(9) . 3_666 N2 K1 N3 91.82(9) 3_656 3_666 N1 K1 N3 136.96(9) 2_645 3_666 N2 K1 N3 135.49(9) 4_565 3_666 N3 K1 N3 69.09(10) 1_545 3_666 O1 K1 O1 139.15(4) . 2_645 N1 K1 O1 117.76(8) . 2_645 N2 K1 O1 76.10(8) 3_656 2_645 N1 K1 O1 69.35(8) 2_645 2_645 N2 K1 O1 71.03(8) 4_565 2_645 N3 K1 O1 75.49(8) 1_545 2_645 N3 K1 O1 143.89(8) 3_666 2_645 O1 K1 K1 111.19(7) . 2_645 N1 K1 K1 153.65(7) . 2_645 N2 K1 K1 44.15(6) 3_656 2_645 N1 K1 K1 42.13(7) 2_645 2_645 N2 K1 K1 88.25(7) 4_565 2_645 N3 K1 K1 95.17(7) 1_545 2_645 N3 K1 K1 135.75(6) 3_666 2_645 O1 K1 K1 40.35(5) 2_645 2_645 O1 K1 K1 47.97(7) . 2_655 N1 K1 K1 43.24(7) . 2_655 N2 K1 K1 144.84(7) 3_656 2_655 N1 K1 K1 84.72(7) 2_645 2_655 N2 K1 K1 43.29(6) 4_565 2_655 N3 K1 K1 132.81(7) 1_545 2_655 N3 K1 K1 95.28(6) 3_666 2_655 O1 K1 K1 114.29(6) 2_645 2_655 K1 K1 K1 122.67(3) 2_645 2_655 C1 N1 K1 137.2(3) . . C1 N1 K1 128.1(3) . 2_655 K1 N1 K1 94.63(10) . 2_655 C22 O1 K1 150.2(3) . . C22 O1 K1 118.0(3) . 2_655 K1 O1 K1 91.68(8) . 2_655 N1 C1 B4 178.3(4) . . C2 N2 K1 130.1(3) . 3_656 C2 N2 K1 126.6(3) . 4_566 K1 N2 K1 92.56(9) 3_656 4_566 C22 O2 C23 116.7(3) . . N2 C2 B4 177.0(4) . . C3 N3 K1 121.6(3) . 1_565 C3 N3 K1 115.8(3) . 3_666 K1 N3 K1 110.91(9) 1_565 3_666 N3 C3 B4 176.6(4) . . C2 B4 C1 106.3(3) . . C2 B4 C3 109.5(3) . . C1 B4 C3 106.0(3) . . C2 B4 C12 110.0(3) . . C1 B4 C12 110.2(3) . . C3 B4 C12 114.4(3) . . C11 C12 C13 115.3(3) . . C11 C12 B4 127.0(3) . . C13 C12 B4 117.7(3) . . F13 C13 C14 118.9(3) . . F13 C13 C12 119.1(3) . . C14 C13 C12 121.9(3) . . F14 C14 C13 118.1(3) . . F14 C14 C15 120.1(3) . . C13 C14 C15 121.7(3) . . C14 C15 C15 119.2(4) . 3_766 C14 C15 C11 124.1(3) . 3_766 C15 C15 C11 116.7(4) 3_766 3_766 C22 C21 H00A 109.5 . . C22 C21 H00B 109.5 . . H00A C21 H00B 109.5 . . C22 C21 H00C 109.5 . . H00A C21 H00C 109.5 . . H00B C21 H00C 109.5 . . O1 C22 O2 123.8(4) . . O1 C22 C21 125.2(4) . . O2 C22 C21 111.1(3) . . O2 C23 C24 106.6(3) . . O2 C23 H00G 110.4 . . C24 C23 H00G 110.4 . . O2 C23 H00H 110.4 . . C24 C23 H00H 110.4 . . H00G C23 H00H 108.6 . . C23 C24 H00D 109.5 . . C23 C24 H00E 109.5 . . H00D C24 H00E 109.5 . . C23 C24 H00F 109.5 . . H00D C24 H00F 109.5 . . H00E C24 H00F 109.5 . . F11 C11 C12 118.1(3) . . F11 C11 C15 116.8(3) . 3_766 C12 C11 C15 125.1(3) . 3_766 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 K1 O1 2.787(3) . K1 N1 2.896(3) . K1 N2 2.953(3) 3_656 K1 N1 2.957(3) 2_645 K1 N2 3.000(3) 4_565 K1 N3 3.017(4) 1_545 K1 N3 3.179(4) 3_666 K1 O1 3.198(3) 2_645 K1 K1 4.3031(7) 2_645 K1 K1 4.3031(7) 2_655 N1 C1 1.138(5) . N1 K1 2.957(3) 2_655 O1 C22 1.212(5) . O1 K1 3.198(3) 2_655 C1 B4 1.600(6) . N2 C2 1.143(5) . N2 K1 2.953(3) 3_656 N2 K1 3.000(3) 4_566 O2 C22 1.336(5) . O2 C23 1.452(5) . C2 B4 1.594(6) . N3 C3 1.139(5) . N3 K1 3.017(4) 1_565 N3 K1 3.179(4) 3_666 C3 B4 1.602(5) . B4 C12 1.630(4) . C12 C11 1.349(5) . C12 C13 1.448(5) . C13 F13 1.312(4) . C13 C14 1.360(5) . C14 F14 1.345(4) . C14 C15 1.394(5) . C15 C15 1.417(7) 3_766 C15 C11 1.440(5) 3_766 C21 C22 1.479(6) . C21 H00A 0.9800 . C21 H00B 0.9800 . C21 H00C 0.9800 . C23 C24 1.500(7) . C23 H00G 0.9900 . C23 H00H 0.9900 . C24 H00D 0.9800 . C24 H00E 0.9800 . C24 H00F 0.9800 . C11 F11 1.337(4) . C11 C15 1.440(5) 3_766