#------------------------------------------------------------------------------ #$Date: 2017-06-27 04:13:01 +0300 (Tue, 27 Jun 2017) $ #$Revision: 198148 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/63/1546390.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_1546390 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 'C16 B2 F8 K2 N8' _chemical_formula_sum 'C16 B2 F8 K2 N8' _chemical_formula_weight 556.06 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.0487(6) _cell_length_b 18.9832(12) _cell_length_c 22.2949(13) _cell_measurement_reflns_used 9894 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.73 _cell_measurement_theta_min 2.33 _cell_volume 4252.9(4) _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 0.0258 _diffrn_reflns_av_unetI/netI 0.0180 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 28164 _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 26.727 _diffrn_reflns_theta_min 1.827 _diffrn_source 'rotating-anode (Nonius FR-591)' _exptl_absorpt_coefficient_mu 0.539 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6724 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SadAbs 2014/5 (Bruker AXS)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.737 _exptl_crystal_description block _exptl_crystal_F_000 2176 _exptl_crystal_size_max 0.360 _exptl_crystal_size_mid 0.340 _exptl_crystal_size_min 0.280 _refine_diff_density_max 1.293 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.085 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_hydrogen_treatment undef _refine_ls_matrix_type full _refine_ls_number_parameters 325 _refine_ls_number_reflns 4508 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.134 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0575 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+10.7837P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1470 _refine_ls_wR_factor_ref 0.1509 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3993 _reflns_number_total 4508 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7sc02249b2.cif _cod_data_source_block JL019_JL_KPy1 _cod_database_code 1546390 _shelx_shelxl_version_number 2014/7 _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_min 0.830 _shelx_estimated_absorpt_t_max 0.864 _shelx_res_file ; fertig_a.res created by SHELXL-2014/7 TITL fertig_a.res in Pbca REM Old TITL fertig in Pbca REM SHELXT solution in Pbca REM R1 0.170, Rweak 0.004, Alpha 0.022, Orientation as input REM Formula found by SHELXT: C17 B2 N8 F7 K2 CELL 0.71073 10.0487 18.9832 22.2949 90.000 90.000 90.000 ZERR 8 0.0006 0.0012 0.0013 0.000 0.000 0.000 LATT 1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C B N F K UNIT 128 16 64 64 16 TEMP -173 SIZE 0.28 0.34 0.36 L.S. 10 BOND $H ACTA 52 LIST 4 FMAP 2 PLAN 20 WGHT 0.058700 10.783700 FVAR 0.10205 K1 5 0.078062 0.300529 0.441579 11.00000 0.01776 0.02081 = 0.02991 -0.00452 -0.00055 -0.00173 N1 3 0.356246 0.296443 0.441640 11.00000 0.02088 0.03245 = 0.02949 0.00218 0.00419 0.00216 F1 4 1.354944 0.659285 0.306376 11.00000 0.03696 0.04503 = 0.03732 0.00488 0.00170 -0.01537 C1 1 0.453872 0.311959 0.419239 11.00000 0.02014 0.01777 = 0.02182 -0.00169 -0.00268 0.00398 B1 2 0.588041 0.339478 0.389398 11.00000 0.01884 0.01391 = 0.02039 -0.00171 -0.00146 0.00110 K2 5 0.670413 0.613775 0.447239 11.00000 0.01484 0.01690 = 0.04606 -0.00584 -0.00334 -0.00019 N2 3 0.804327 0.265048 0.429191 11.00000 0.01838 0.02861 = 0.02463 0.00191 -0.00050 0.00039 F2 4 1.323624 0.656030 0.188778 11.00000 0.04848 0.04918 = 0.04681 0.01346 0.01580 -0.00107 C2 1 0.712165 0.295547 0.413861 11.00000 0.01640 0.01784 = 0.01898 -0.00031 0.00059 -0.00270 B2 2 1.179916 0.578646 0.395580 11.00000 0.01184 0.01568 = 0.03079 -0.00184 0.00117 -0.00178 F3 4 0.975910 0.507638 0.201647 11.00000 0.03560 0.04175 = 0.03875 -0.00999 -0.00750 0.00272 N3 3 0.614951 0.475156 0.429156 11.00000 0.06760 0.02140 = 0.03020 -0.00356 -0.00720 -0.00272 C3 1 0.605026 0.418764 0.411642 11.00000 0.03021 0.01968 = 0.02289 0.00369 -0.00213 -0.00034 F4 4 0.989666 0.503373 0.322061 11.00000 0.02605 0.03584 = 0.03946 -0.00326 0.00035 -0.01249 N4 3 0.952240 0.638353 0.441205 11.00000 0.01721 0.02463 = 0.03007 -0.00273 0.00296 0.00139 C4 1 1.047451 0.614061 0.422169 11.00000 0.01650 0.01781 = 0.02774 -0.00097 -0.00182 -0.00487 F5 4 0.773518 0.409121 0.308428 11.00000 0.02727 0.03212 = 0.03297 -0.00178 0.00220 -0.01254 N5 3 1.185569 0.444349 0.441941 11.00000 0.03041 0.02083 = 0.03740 -0.00101 0.00303 -0.00052 C5 1 1.184992 0.499967 0.421597 11.00000 0.01758 0.02037 = 0.03011 -0.00414 0.00232 -0.00121 F6 4 0.770585 0.399995 0.188716 11.00000 0.03737 0.03907 = 0.03024 0.01076 0.00955 0.00158 N6 3 1.393052 0.649574 0.442551 11.00000 0.01737 0.02123 = 0.03014 0.00026 -0.00065 -0.00132 C6 1 1.304573 0.620266 0.422536 11.00000 0.01510 0.01556 = 0.02643 0.00047 0.00413 0.00272 F7 4 0.419810 0.251679 0.191264 11.00000 0.04016 0.04222 = 0.03760 -0.00920 -0.01823 -0.00062 N7 3 1.150359 0.581971 0.195194 11.00000 0.03356 0.02927 = 0.03719 -0.00009 0.00230 0.00975 C7 1 0.586722 0.333829 0.316419 11.00000 0.01574 0.01390 = 0.02133 0.00050 -0.00229 0.00438 C8 1 0.679477 0.369518 0.281860 11.00000 0.01971 0.01809 = 0.02349 0.00078 -0.00128 0.00205 F8 4 0.405551 0.253370 0.309578 11.00000 0.02994 0.03402 = 0.03468 -0.00373 -0.00030 -0.01344 N8 3 0.593953 0.326181 0.189875 11.00000 0.03022 0.03012 = 0.02320 -0.00025 -0.00535 0.00910 C9 1 0.679378 0.364522 0.220286 11.00000 0.02475 0.02339 = 0.02821 0.00685 0.00445 0.00765 C10 1 0.498852 0.292996 0.283519 11.00000 0.01965 0.01936 = 0.03002 0.00111 -0.00304 0.00120 C11 1 0.506842 0.291272 0.221890 11.00000 0.02579 0.02578 = 0.02930 -0.00362 -0.01049 0.00671 C12 1 1.174471 0.580224 0.322473 11.00000 0.01678 0.01638 = 0.03311 -0.00200 0.00320 0.00514 C13 1 1.257649 0.618907 0.285146 11.00000 0.01739 0.01797 = 0.05152 0.00050 0.00597 0.00080 C14 1 1.241348 0.617767 0.223513 11.00000 0.03204 0.02821 = 0.04113 0.00750 0.01089 0.00685 C15 1 1.078019 0.542394 0.291477 11.00000 0.01967 0.02000 = 0.03438 -0.00259 0.00449 0.00156 C16 1 1.069651 0.544473 0.229846 11.00000 0.02665 0.02254 = 0.03471 -0.00676 -0.00405 0.00516 HKLF 4 REM fertig_a.res in Pbca REM R1 = 0.0575 for 3993 Fo > 4sig(Fo) and 0.0642 for all 4508 data REM 325 parameters refined using 0 restraints END WGHT 0.0587 10.7837 REM Highest difference peak 1.293, deepest hole -0.546, 1-sigma level 0.085 Q1 1 1.1683 0.5982 0.1508 11.00000 0.05 1.29 Q2 1 0.0793 0.2871 0.4766 11.00000 0.05 1.23 Q3 1 0.6490 0.6119 0.4807 11.00000 0.05 1.13 Q4 1 1.3546 0.6642 0.2273 11.00000 0.05 0.92 Q5 1 0.5845 0.3263 0.1450 11.00000 0.05 0.70 Q6 1 0.5800 0.3378 0.3542 11.00000 0.05 0.47 Q7 1 0.6335 0.6401 0.4183 11.00000 0.05 0.41 Q8 1 0.4755 0.3042 0.2520 11.00000 0.05 0.38 Q9 1 1.1742 0.5837 0.3553 11.00000 0.05 0.38 Q10 1 1.2835 0.6094 0.2535 11.00000 0.05 0.34 Q11 1 0.5199 0.3216 0.3996 11.00000 0.05 0.34 Q12 1 1.1605 0.4875 0.4518 11.00000 0.05 0.34 Q13 1 0.1185 0.3137 0.3970 11.00000 0.05 0.32 Q14 1 0.7847 0.2961 0.4102 11.00000 0.05 0.32 Q15 1 1.1824 0.6018 0.2215 11.00000 0.05 0.31 Q16 1 0.6648 0.3214 0.3977 11.00000 0.05 0.31 Q17 1 1.1031 0.6025 0.4079 11.00000 0.05 0.30 Q18 1 0.6447 0.3831 0.2502 11.00000 0.05 0.30 Q19 1 1.0154 0.6249 0.4507 11.00000 0.05 0.30 Q20 1 0.5976 0.3729 0.3995 11.00000 0.05 0.29 ; _shelx_res_checksum 91009 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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_site_symmetry_order _atom_site_calc_flag K1 K 0.07806(7) 0.30053(3) 0.44158(3) 0.02283(18) Uani 1 1 d N1 N 0.3562(3) 0.29644(15) 0.44164(12) 0.0276(6) Uani 1 1 d F1 F 1.3549(2) 0.65928(12) 0.30638(9) 0.0398(5) Uani 1 1 d C1 C 0.4539(3) 0.31196(15) 0.41924(13) 0.0199(6) Uani 1 1 d B1 B 0.5880(3) 0.33948(17) 0.38940(15) 0.0177(6) Uani 1 1 d K2 K 0.67041(6) 0.61378(3) 0.44724(3) 0.02593(19) Uani 1 1 d N2 N 0.8043(3) 0.26505(14) 0.42919(12) 0.0239(6) Uani 1 1 d F2 F 1.3236(2) 0.65603(13) 0.18878(11) 0.0482(6) Uani 1 1 d C2 C 0.7122(3) 0.29555(15) 0.41386(13) 0.0177(6) Uani 1 1 d B2 B 1.1799(3) 0.57865(17) 0.39558(16) 0.0194(7) Uani 1 1 d F3 F 0.9759(2) 0.50764(12) 0.20165(10) 0.0387(5) Uani 1 1 d N3 N 0.6150(4) 0.47516(16) 0.42916(14) 0.0397(8) Uani 1 1 d C3 C 0.6050(3) 0.41876(16) 0.41164(14) 0.0243(7) Uani 1 1 d F4 F 0.9897(2) 0.50337(11) 0.32206(9) 0.0338(5) Uani 1 1 d N4 N 0.9522(3) 0.63835(14) 0.44120(12) 0.0240(6) Uani 1 1 d C4 C 1.0475(3) 0.61406(15) 0.42217(14) 0.0207(6) Uani 1 1 d F5 F 0.77352(19) 0.40912(10) 0.30843(8) 0.0308(4) Uani 1 1 d N5 N 1.1856(3) 0.44435(15) 0.44194(13) 0.0295(6) Uani 1 1 d C5 C 1.1850(3) 0.49997(16) 0.42160(14) 0.0227(6) Uani 1 1 d F6 F 0.7706(2) 0.39999(11) 0.18872(9) 0.0356(5) Uani 1 1 d N6 N 1.3931(3) 0.64957(14) 0.44255(12) 0.0229(6) Uani 1 1 d C6 C 1.3046(3) 0.62027(15) 0.42254(14) 0.0190(6) Uani 1 1 d F7 F 0.4198(2) 0.25168(12) 0.19126(9) 0.0400(5) Uani 1 1 d N7 N 1.1504(3) 0.58197(16) 0.19519(14) 0.0333(7) Uani 1 1 d C7 C 0.5867(3) 0.33383(14) 0.31642(13) 0.0170(6) Uani 1 1 d C8 C 0.6795(3) 0.36952(16) 0.28186(13) 0.0204(6) Uani 1 1 d F8 F 0.4056(2) 0.25337(11) 0.30958(9) 0.0329(5) Uani 1 1 d N8 N 0.5940(3) 0.32618(15) 0.18988(12) 0.0278(6) Uani 1 1 d C9 C 0.6794(3) 0.36452(17) 0.22029(15) 0.0255(7) Uani 1 1 d C10 C 0.4989(3) 0.29300(16) 0.28352(15) 0.0230(6) Uani 1 1 d C11 C 0.5068(3) 0.29127(17) 0.22189(15) 0.0270(7) Uani 1 1 d C12 C 1.1745(3) 0.58022(16) 0.32247(14) 0.0221(6) Uani 1 1 d C13 C 1.2576(3) 0.61891(17) 0.28515(17) 0.0290(7) Uani 1 1 d C14 C 1.2413(4) 0.61777(19) 0.22351(17) 0.0338(8) Uani 1 1 d C15 C 1.0780(3) 0.54239(16) 0.29148(15) 0.0247(7) Uani 1 1 d C16 C 1.0697(3) 0.54447(17) 0.22985(16) 0.0280(7) 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 0.0178(3) 0.0208(3) 0.0299(4) -0.0045(3) -0.0006(3) -0.0017(2) N1 0.0209(14) 0.0325(15) 0.0295(14) 0.0022(12) 0.0042(11) 0.0022(12) F1 0.0370(12) 0.0450(13) 0.0373(11) 0.0049(10) 0.0017(9) -0.0154(10) C1 0.0201(15) 0.0178(14) 0.0218(14) -0.0017(11) -0.0027(12) 0.0040(12) B1 0.0188(16) 0.0139(14) 0.0204(15) -0.0017(12) -0.0015(12) 0.0011(12) K2 0.0148(3) 0.0169(3) 0.0461(4) -0.0058(3) -0.0033(3) -0.0002(2) N2 0.0184(13) 0.0286(14) 0.0246(13) 0.0019(11) -0.0005(10) 0.0004(11) F2 0.0485(14) 0.0492(14) 0.0468(13) 0.0135(11) 0.0158(11) -0.0011(11) C2 0.0164(14) 0.0178(14) 0.0190(13) -0.0003(11) 0.0006(11) -0.0027(11) B2 0.0118(15) 0.0157(15) 0.0308(18) -0.0018(13) 0.0012(13) -0.0018(12) F3 0.0356(12) 0.0418(12) 0.0387(11) -0.0100(9) -0.0075(9) 0.0027(10) N3 0.068(2) 0.0214(15) 0.0302(15) -0.0036(12) -0.0072(15) -0.0027(15) C3 0.0302(17) 0.0197(15) 0.0229(15) 0.0037(12) -0.0021(13) -0.0003(13) F4 0.0261(10) 0.0358(11) 0.0395(11) -0.0033(9) 0.0003(8) -0.0125(9) N4 0.0172(13) 0.0246(13) 0.0301(14) -0.0027(11) 0.0030(11) 0.0014(11) C4 0.0165(14) 0.0178(14) 0.0277(15) -0.0010(12) -0.0018(12) -0.0049(12) F5 0.0273(10) 0.0321(10) 0.0330(10) -0.0018(8) 0.0022(8) -0.0125(8) N5 0.0304(15) 0.0208(14) 0.0374(16) -0.0010(12) 0.0030(12) -0.0005(12) C5 0.0176(14) 0.0204(15) 0.0301(16) -0.0041(12) 0.0023(12) -0.0012(12) F6 0.0374(11) 0.0391(12) 0.0302(10) 0.0108(9) 0.0095(9) 0.0016(9) N6 0.0174(13) 0.0212(13) 0.0301(14) 0.0003(11) -0.0006(11) -0.0013(11) C6 0.0151(14) 0.0156(13) 0.0264(15) 0.0005(11) 0.0041(12) 0.0027(11) F7 0.0402(12) 0.0422(12) 0.0376(12) -0.0092(9) -0.0182(9) -0.0006(10) N7 0.0336(16) 0.0293(15) 0.0372(16) -0.0001(13) 0.0023(13) 0.0097(13) C7 0.0157(13) 0.0139(13) 0.0213(14) 0.0005(10) -0.0023(11) 0.0044(11) C8 0.0197(14) 0.0181(14) 0.0235(15) 0.0008(11) -0.0013(11) 0.0021(12) F8 0.0299(10) 0.0340(11) 0.0347(11) -0.0037(8) -0.0003(8) -0.0134(9) N8 0.0302(15) 0.0301(14) 0.0232(13) -0.0003(11) -0.0053(11) 0.0091(12) C9 0.0248(16) 0.0234(16) 0.0282(16) 0.0069(13) 0.0045(13) 0.0077(13) C10 0.0197(15) 0.0194(14) 0.0300(17) 0.0011(12) -0.0030(12) 0.0012(12) C11 0.0258(16) 0.0258(16) 0.0293(17) -0.0036(13) -0.0105(13) 0.0067(13) C12 0.0168(14) 0.0164(14) 0.0331(16) -0.0020(12) 0.0032(12) 0.0051(11) C13 0.0174(15) 0.0180(15) 0.052(2) 0.0005(14) 0.0060(14) 0.0008(12) C14 0.0320(18) 0.0282(17) 0.0411(19) 0.0075(15) 0.0109(16) 0.0069(15) C15 0.0197(15) 0.0200(15) 0.0344(17) -0.0026(12) 0.0045(13) 0.0016(12) C16 0.0267(16) 0.0225(16) 0.0347(17) -0.0068(13) -0.0041(14) 0.0052(13) 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' B B 0.0013 0.0007 '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' 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 N1 K1 N2 163.70(9) . 1_455 N1 K1 N4 96.70(8) . 5_666 N2 K1 N4 94.67(8) 1_455 5_666 N1 K1 N6 82.63(8) . 8_755 N2 K1 N6 82.10(8) 1_455 8_755 N4 K1 N6 113.91(8) 5_666 8_755 N1 K1 N5 70.00(9) . 1_455 N2 K1 N5 125.18(8) 1_455 1_455 N4 K1 N5 70.20(8) 5_666 1_455 N6 K1 N5 152.62(8) 8_755 1_455 N1 K1 N8 87.21(8) . 6_556 N2 K1 N8 89.72(8) 1_455 6_556 N4 K1 N8 146.60(8) 5_666 6_556 N6 K1 N8 99.49(8) 8_755 6_556 N5 K1 N8 80.26(8) 1_455 6_556 N1 K1 K2 50.42(6) . 5_666 N2 K1 K2 141.98(6) 1_455 5_666 N4 K1 K2 47.31(5) 5_666 5_666 N6 K1 K2 110.20(6) 8_755 5_666 N5 K1 K2 51.05(6) 1_455 5_666 N8 K1 K2 121.57(6) 6_556 5_666 N1 K1 K2 123.55(6) . 8_655 N2 K1 K2 41.66(6) 1_455 8_655 N4 K1 K2 104.03(6) 5_666 8_655 N6 K1 K2 40.95(5) 8_755 8_655 N5 K1 K2 166.31(6) 1_455 8_655 N8 K1 K2 101.14(6) 6_556 8_655 K2 K1 K2 134.117(19) 5_666 8_655 C1 N1 K1 148.6(2) . . C1 N1 K2 106.9(2) . 5_666 K1 N1 K2 84.03(8) . 5_666 N1 C1 B1 175.8(3) . . N1 C1 K2 55.1(2) . 5_666 B1 C1 K2 121.48(18) . 5_666 C1 B1 C3 105.7(2) . . C1 B1 C2 110.3(2) . . C3 B1 C2 107.7(2) . . C1 B1 C7 112.9(2) . . C3 B1 C7 111.9(2) . . C2 B1 C7 108.2(2) . . N3 K2 N6 91.42(10) . 1_455 N3 K2 N4 110.62(10) . . N6 K2 N4 156.46(8) 1_455 . N3 K2 N2 162.15(9) . 8_765 N6 K2 N2 81.15(7) 1_455 8_765 N4 K2 N2 75.37(8) . 8_765 N3 K2 N1 130.52(9) . 5_666 N6 K2 N1 79.05(8) 1_455 5_666 N4 K2 N1 91.96(8) . 5_666 N2 K2 N1 64.16(8) 8_765 5_666 N3 K2 N5 82.42(9) . 5_766 N6 K2 N5 124.91(8) 1_455 5_766 N4 K2 N5 68.36(8) . 5_766 N2 K2 N5 115.15(8) 8_765 5_766 N1 K2 N5 65.43(8) 5_666 5_766 N3 K2 N7 70.22(9) . 6_556 N6 K2 N7 87.02(8) 1_455 6_556 N4 K2 N7 92.62(8) . 6_556 N2 K2 N7 93.08(8) 8_765 6_556 N1 K2 N7 154.73(8) 5_666 6_556 N5 K2 N7 138.74(8) 5_766 6_556 N3 K2 C1 116.09(9) . 5_666 N6 K2 C1 65.91(7) 1_455 5_666 N4 K2 C1 108.91(7) . 5_666 N2 K2 C1 75.69(7) 8_765 5_666 N1 K2 C1 18.03(7) 5_666 5_666 N5 K2 C1 68.33(7) 5_766 5_666 N7 K2 C1 151.78(7) 6_556 5_666 N3 K2 K1 129.14(8) . 5_666 N6 K2 K1 123.65(6) 1_455 5_666 N4 K2 K1 47.36(5) . 5_666 N2 K2 K1 67.63(5) 8_765 5_666 N1 K2 K1 45.55(6) 5_666 5_666 N5 K2 K1 48.08(5) 5_766 5_666 N7 K2 K1 137.90(6) 6_556 5_666 C1 K2 K1 61.66(5) 5_666 5_666 N3 K2 K1 131.95(8) . 8_665 N6 K2 K1 41.12(5) 1_455 8_665 N4 K2 K1 115.67(6) . 8_665 N2 K2 K1 40.53(5) 8_765 8_665 N1 K2 K1 60.75(6) 5_666 8_665 N5 K2 K1 126.07(6) 5_766 8_665 N7 K2 K1 95.05(5) 6_556 8_665 C1 K2 K1 59.57(5) 5_666 8_665 K1 K2 K1 92.904(15) 5_666 8_665 C2 N2 K1 133.8(2) . 1_655 C2 N2 K2 127.7(2) . 8_755 K1 N2 K2 97.81(8) 1_655 8_755 N2 C2 B1 176.9(3) . . C6 B2 C5 107.4(2) . . C6 B2 C4 107.7(2) . . C5 B2 C4 106.4(2) . . C6 B2 C12 113.1(3) . . C5 B2 C12 112.3(2) . . C4 B2 C12 109.5(2) . . C3 N3 K2 166.9(3) . . N3 C3 B1 177.9(4) . . C4 N4 K2 140.9(2) . . C4 N4 K1 126.1(2) . 5_666 K2 N4 K1 85.33(7) . 5_666 N4 C4 B2 179.0(3) . . C5 N5 K1 148.4(3) . 1_655 C5 N5 K2 130.6(2) . 5_766 K1 N5 K2 80.87(7) 1_655 5_766 N5 C5 B2 177.5(3) . . C6 N6 K2 131.0(2) . 1_655 C6 N6 K1 124.1(2) . 8_765 K2 N6 K1 97.93(8) 1_655 8_765 N6 C6 B2 179.0(3) . . C14 N7 C16 115.3(3) . . C14 N7 K2 109.5(2) . 6_656 C16 N7 K2 135.1(2) . 6_656 C10 C7 C8 114.1(3) . . C10 C7 B1 124.8(3) . . C8 C7 B1 121.1(3) . . F5 C8 C9 118.6(3) . . F5 C8 C7 120.1(3) . . C9 C8 C7 121.4(3) . . C11 N8 C9 115.8(3) . . C11 N8 K1 114.7(2) . 6_656 C9 N8 K1 129.3(2) . 6_656 N8 C9 F6 117.1(3) . . N8 C9 C8 123.6(3) . . F6 C9 C8 119.3(3) . . F8 C10 C11 117.5(3) . . F8 C10 C7 122.2(3) . . C11 C10 C7 120.3(3) . . N8 C11 F7 116.3(3) . . N8 C11 C10 124.8(3) . . F7 C11 C10 118.9(3) . . C13 C12 C15 113.2(3) . . C13 C12 B2 126.0(3) . . C15 C12 B2 120.7(3) . . F1 C13 C14 116.7(3) . . F1 C13 C12 122.3(3) . . C14 C13 C12 121.0(3) . . N7 C14 F2 115.7(3) . . N7 C14 C13 124.9(3) . . F2 C14 C13 119.4(3) . . F4 C15 C16 118.8(3) . . F4 C15 C12 119.6(3) . . C16 C15 C12 121.6(3) . . N7 C16 F3 116.1(3) . . N7 C16 C15 124.0(3) . . F3 C16 C15 120.0(3) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 K1 N1 2.796(3) . K1 N2 2.845(3) 1_455 K1 N4 2.875(3) 5_666 K1 N6 2.880(3) 8_755 K1 N5 2.936(3) 1_455 K1 N8 2.975(3) 6_556 K1 K2 3.8961(10) 5_666 K1 K2 4.3380(10) 8_655 N1 C1 1.140(4) . N1 K2 3.019(3) 5_666 F1 C13 1.329(4) . C1 B1 1.592(4) . C1 K2 3.523(3) 5_666 B1 C3 1.594(4) . B1 C2 1.596(4) . B1 C7 1.631(4) . K2 N3 2.720(3) . K2 N6 2.871(3) 1_455 K2 N4 2.873(3) . K2 N2 2.911(3) 8_765 K2 N1 3.019(3) 5_666 K2 N5 3.069(3) 5_766 K2 N7 3.239(3) 6_556 K2 C1 3.523(3) 5_666 K2 K1 3.8960(10) 5_666 K2 K1 4.3380(10) 8_665 N2 C2 1.144(4) . N2 K1 2.845(3) 1_655 N2 K2 2.911(3) 8_755 F2 C14 1.346(4) . B2 C6 1.598(4) . B2 C5 1.603(4) . B2 C4 1.605(4) . B2 C12 1.631(5) . F3 C16 1.331(4) . N3 C3 1.144(4) . F4 C15 1.342(4) . N4 C4 1.144(4) . N4 K1 2.875(3) 5_666 F5 C8 1.345(3) . N5 C5 1.149(4) . N5 K1 2.936(3) 1_655 N5 K2 3.069(3) 5_766 F6 C9 1.337(4) . N6 C6 1.140(4) . N6 K2 2.871(3) 1_655 N6 K1 2.880(3) 8_765 F7 C11 1.340(4) . N7 C14 1.302(5) . N7 C16 1.327(5) . N7 K2 3.239(3) 6_656 C7 C10 1.385(4) . C7 C8 1.386(4) . C8 C9 1.376(4) . F8 C10 1.335(4) . N8 C11 1.310(5) . N8 C9 1.314(4) . N8 K1 2.975(3) 6_656 C10 C11 1.377(4) . C12 C13 1.389(4) . C12 C15 1.390(4) . C13 C14 1.384(5) . C15 C16 1.377(5) .