#------------------------------------------------------------------------------ #$Date: 2017-06-27 04:13:01 +0300 (Tue, 27 Jun 2017) $ #$Revision: 198148 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/63/1546388.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_1546388 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 'C14 H6 B2 F3 K2 N7 O' _chemical_formula_sum 'C14 H6 B2 F3 K2 N7 O' _chemical_formula_weight 445.08 _space_group_crystal_system tetragonal _space_group_IT_number 88 _space_group_name_Hall '-I 4ad' _space_group_name_H-M_alt 'I 41/a' _symmetry_space_group_name_Hall '-I 4ad' _symmetry_space_group_name_H-M 'I 41/a :2' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 25.5118(15) _cell_length_b 25.5118(15) _cell_length_c 12.1914(8) _cell_measurement_reflns_used 6721 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 24.30 _cell_measurement_theta_min 2.26 _cell_volume 7934.8(8) _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 0.999 _diffrn_measured_fraction_theta_max 0.994 _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 0.0442 _diffrn_reflns_av_unetI/netI 0.0292 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 31833 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.030 _diffrn_reflns_theta_min 1.596 _diffrn_source 'rotating-anode (Nonius FR-591)' _exptl_absorpt_coefficient_mu 0.525 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SadAbs 2014/5 (Bruker AXS)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.490 _exptl_crystal_description plate _exptl_crystal_F_000 3552 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _refine_diff_density_max 1.210 _refine_diff_density_min -0.857 _refine_diff_density_rms 0.094 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.272 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 322 _refine_ls_number_reflns 3902 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.273 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0734 _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^)+(0.0106P)^2^+57.2601P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1464 _refine_ls_wR_factor_ref 0.1519 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3088 _reflns_number_total 3902 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7sc02249b2.cif _cod_data_source_block JL037_JL_K2Py2acetone _cod_original_cell_volume 7934.8(11) _cod_database_code 1546388 _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_res_file ; JL037_B2-Perflourpyridin.res created by SHELXL-2014/7 TITL test_a.res in I4(1)/a REM Old TITL test in I4(1)/a REM SHELXT solution in I4(1)/a REM R1 0.248, Rweak 0.021, Alpha 0.034, Orientation as input REM Formula found by SHELXT: C11 B2 N9 F3 K2 CELL 0.71073 25.5118 25.5118 12.1914 90.000 90.000 90.000 ZERR 16 0.0015 0.0015 0.0008 0.000 0.000 0.000 LATT 2 SYMM 1/2-X, -Y, 1/2+Z SYMM 3/4-Y, 1/4+X, 1/4+Z SYMM 3/4+Y, 3/4-X, 3/4+Z SFAC C B N F K O H UNIT 224 32 112 48 32 16 96 TEMP -173 OMIT 0 53 ACTA BOND $H L.S. 20 LIST 4 FMAP 2 PLAN 20 EADP B2 B20 ISOR 0.02 C21 N21 WGHT 0.010620 57.260101 FVAR 0.12771 0.75628 N1 3 0.421651 0.533933 0.468878 11.00000 0.01545 0.02742 = 0.02113 0.00158 0.00257 0.00260 C1 1 0.458908 0.555762 0.524877 11.00000 0.01947 0.02691 = 0.03079 0.00140 0.00854 0.00023 F1 4 0.482769 0.597331 0.477570 11.00000 0.03299 0.04166 = 0.04439 0.00621 0.00645 -0.01456 C2 1 0.474412 0.540777 0.628495 11.00000 0.01661 0.03982 = 0.02736 -0.01063 -0.00290 0.00315 F2 4 0.511619 0.568136 0.678791 11.00000 0.03017 0.07247 = 0.04631 -0.01320 -0.01146 -0.00711 C3 1 0.451213 0.498873 0.678882 11.00000 0.03101 0.03581 = 0.02012 -0.00209 -0.00114 0.01144 PART 1 B2 2 0.464230 0.482655 0.804902 21.00000 0.01355 0.04830 = 0.02284 -0.00042 -0.00625 0.00454 C9 1 0.429686 0.436565 0.856866 21.00000 0.02798 0.05663 = 0.01721 0.00884 -0.00190 0.01666 N9 3 0.404884 0.404604 0.898828 21.00000 0.04466 0.06949 = 0.02822 0.02321 0.00317 0.01276 C10 1 0.453763 0.531603 0.880759 21.00000 0.03083 0.06574 = 0.01625 0.00608 -0.00022 0.00011 N10 3 0.442609 0.566926 0.934719 21.00000 0.07043 0.07068 = 0.02969 -0.01027 0.01096 0.00020 C11 1 0.524118 0.465696 0.809628 21.00000 0.02325 0.08968 = 0.01777 0.00869 -0.00083 0.00898 N11 3 0.566876 0.452059 0.811199 21.00000 0.02582 0.12952 = 0.03786 0.01315 -0.00489 0.01606 PART 2 B20 2 0.485954 0.478699 0.793261 -21.00000 0.01355 0.04830 = 0.02284 -0.00042 -0.00625 0.00454 C20 1 0.537533 0.509471 0.829104 -21.00000 0.03257 0.03123 = 0.02387 -0.00683 -0.01498 0.01339 N20 3 0.575740 0.528022 0.856375 -21.00000 0.01901 0.05934 = 0.02834 0.00881 -0.01351 0.00533 C21 1 0.442573 0.477406 0.886982 -21.00000 0.02269 0.07575 = 0.01315 -0.00850 -0.00155 0.01734 N21 3 0.412973 0.474908 0.956472 -21.00000 0.04231 0.11240 = 0.04173 -0.01014 -0.00314 0.02408 C22 1 0.499693 0.418779 0.776838 -21.00000 0.04265 0.04342 = 0.01403 0.00719 -0.00271 0.00247 N22 3 0.511498 0.376024 0.767193 -21.00000 0.11295 0.05639 = 0.04269 0.01342 -0.02375 0.00624 PART 0 C4 1 0.412475 0.475579 0.615969 11.00000 0.02893 0.02467 = 0.01957 0.00099 0.00542 0.00610 F4 4 0.387690 0.432494 0.657666 11.00000 0.05298 0.02807 = 0.02871 0.01075 0.00674 -0.00068 C5 1 0.396597 0.492556 0.514276 11.00000 0.01701 0.02489 = 0.01704 -0.00115 0.00448 0.00541 B1 2 0.348820 0.466939 0.444103 11.00000 0.02313 0.02796 = 0.02523 -0.00213 0.00240 -0.00443 C6 1 0.368083 0.418491 0.372590 11.00000 0.02137 0.04937 = 0.05452 -0.02328 0.00575 -0.01116 N6 3 0.381642 0.383956 0.321122 11.00000 0.03002 0.07803 = 0.10775 -0.06150 0.00561 -0.00832 C7 1 0.325953 0.510231 0.362531 11.00000 0.02038 0.05011 = 0.02496 0.00150 -0.00326 -0.01231 N7 3 0.309576 0.542203 0.306277 11.00000 0.03223 0.07407 = 0.04029 0.02489 -0.01590 -0.01544 C8 1 0.301740 0.447244 0.520548 11.00000 0.02439 0.02689 = 0.02995 0.00278 0.00223 0.00289 N8 3 0.268100 0.433624 0.574857 11.00000 0.02517 0.04437 = 0.03776 0.01405 0.00730 0.00149 K1 5 0.159336 0.454925 0.560034 11.00000 0.02392 0.04570 = 0.02852 -0.00056 0.00771 0.00271 K2 5 0.379208 0.360323 1.094570 11.00000 0.04442 0.06472 = 0.05390 0.01804 0.01250 0.00892 O1 6 0.472172 0.318269 1.107262 11.00000 0.05988 0.12226 = 0.23194 0.01032 0.00700 0.01873 C12 1 0.518975 0.317319 1.119966 11.00000 0.06169 0.12863 = 0.25725 0.04107 0.02182 0.01682 C13 1 0.552417 0.310574 1.006556 11.00000 0.11188 0.20030 = 0.37339 -0.13009 0.13726 -0.03446 AFIX 137 H13A 7 0.580691 0.285154 1.018024 11.00000 -1.50000 H13B 7 0.567441 0.344461 0.985468 11.00000 -1.50000 H13C 7 0.529180 0.298060 0.948148 11.00000 -1.50000 AFIX 0 C14 1 0.540630 0.314427 1.235826 11.00000 0.32234 0.22064 = 0.31484 -0.09513 -0.22760 0.13375 AFIX 137 H14A 7 0.579003 0.313226 1.233093 11.00000 -1.50000 H14B 7 0.527409 0.282772 1.271993 11.00000 -1.50000 H14C 7 0.529454 0.345419 1.277165 11.00000 -1.50000 AFIX 0 HKLF 4 REM test_a.res in I4(1)/a REM R1 = 0.0734 for 3088 Fo > 4sig(Fo) and 0.0933 for all 3902 data REM 322 parameters refined using 12 restraints END WGHT 0.0938 48.8391 REM Highest difference peak 1.210, deepest hole -0.857, 1-sigma level 0.094 Q1 1 0.6020 0.3645 0.8975 11.00000 0.05 1.21 Q2 1 0.1624 0.4866 0.5751 11.00000 0.05 0.82 Q3 1 0.5000 0.2500 0.8750 10.25000 0.05 0.77 Q4 1 0.4178 0.5578 0.3932 11.00000 0.05 0.73 Q5 1 0.4231 0.3479 1.1097 11.00000 0.05 0.65 Q6 1 0.4453 0.6187 0.9128 11.00000 0.05 0.49 Q7 1 0.5783 0.2382 1.0443 11.00000 0.05 0.43 Q8 1 0.4138 0.4775 0.5573 11.00000 0.05 0.33 Q9 1 0.4151 0.4290 0.6881 11.00000 0.05 0.33 Q10 1 0.5265 0.5866 0.6255 11.00000 0.05 0.32 Q11 1 0.4202 0.5177 0.9381 11.00000 0.05 0.31 Q12 1 0.5181 0.3183 0.9866 11.00000 0.05 0.30 Q13 1 0.3892 0.3839 1.0294 11.00000 0.05 0.29 Q14 1 0.5515 0.3054 1.1869 11.00000 0.05 0.29 Q15 1 0.5608 0.3018 1.0412 11.00000 0.05 0.29 Q16 1 0.4328 0.4865 0.6515 11.00000 0.05 0.29 Q17 1 0.1608 0.4331 0.6034 11.00000 0.05 0.28 Q18 1 0.4680 0.5081 0.6451 11.00000 0.05 0.28 Q19 1 0.4739 0.4932 0.6873 11.00000 0.05 0.28 Q20 1 0.4417 0.5075 0.6996 11.00000 0.05 0.28 ; _shelx_res_checksum 95662 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' 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 N1 N 0.42165(12) 0.53393(13) 0.4689(3) 0.0213(7) Uani 1 1 d . . . . . C1 C 0.45891(15) 0.55576(16) 0.5249(3) 0.0257(9) Uani 1 1 d . . . . . F1 F 0.48277(10) 0.59733(10) 0.4776(2) 0.0397(7) Uani 1 1 d . . . . . C2 C 0.47441(15) 0.54078(18) 0.6285(3) 0.0279(10) Uani 1 1 d . . . . . F2 F 0.51162(10) 0.56814(12) 0.6788(2) 0.0496(8) Uani 1 1 d . . . . . C3 C 0.45121(17) 0.49887(17) 0.6789(3) 0.0290(10) Uani 1 1 d . . . . . B2 B 0.4642(3) 0.4827(3) 0.8049(6) 0.0282(16) Uani 0.756(4) 1 d . . P A 1 C9 C 0.4297(2) 0.4366(3) 0.8569(5) 0.0339(15) Uani 0.756(4) 1 d . . P A 1 N9 N 0.4049(2) 0.4046(3) 0.8988(4) 0.0475(16) Uani 0.756(4) 1 d . . P A 1 C10 C 0.4538(2) 0.5316(3) 0.8808(5) 0.0376(16) Uani 0.756(4) 1 d . . P A 1 N10 N 0.4426(3) 0.5669(3) 0.9347(5) 0.0569(18) Uani 0.756(4) 1 d . . P A 1 C11 C 0.5241(2) 0.4657(3) 0.8096(5) 0.0436(19) Uani 0.756(4) 1 d . . P A 1 N11 N 0.5669(2) 0.4521(3) 0.8112(5) 0.064(2) Uani 0.756(4) 1 d . . P A 1 B20 B 0.4860(10) 0.4787(12) 0.793(2) 0.0282(16) Uani 0.244(4) 1 d . . P A 2 C20 C 0.5375(7) 0.5095(7) 0.8291(14) 0.029(4) Uani 0.244(4) 1 d . . P A 2 N20 N 0.5757(6) 0.5280(7) 0.8564(12) 0.036(4) Uani 0.244(4) 1 d . . P A 2 C21 C 0.4426(7) 0.4774(10) 0.8870(15) 0.037(5) Uani 0.244(4) 1 d . U P A 2 N21 N 0.4130(8) 0.4749(10) 0.9565(16) 0.065(6) Uani 0.244(4) 1 d . U P A 2 C22 C 0.4997(8) 0.4188(8) 0.7768(14) 0.033(5) Uani 0.244(4) 1 d . . P A 2 N22 N 0.5115(10) 0.3760(9) 0.7672(17) 0.071(7) Uani 0.244(4) 1 d . . P A 2 C4 C 0.41248(16) 0.47558(16) 0.6160(3) 0.0244(9) Uani 1 1 d . . . . . F4 F 0.38769(11) 0.43249(9) 0.6577(2) 0.0366(6) Uani 1 1 d . . . . . C5 C 0.39660(14) 0.49256(15) 0.5143(3) 0.0196(8) Uani 1 1 d . . . . . B1 B 0.34882(18) 0.46694(19) 0.4441(4) 0.0254(10) Uani 1 1 d . . . . . C6 C 0.36808(17) 0.4185(2) 0.3726(4) 0.0418(13) Uani 1 1 d . . . . . N6 N 0.38164(17) 0.3840(2) 0.3211(5) 0.0719(18) Uani 1 1 d . . . . . C7 C 0.32595(16) 0.51023(19) 0.3625(4) 0.0318(10) Uani 1 1 d . . . . . N7 N 0.30958(16) 0.54220(19) 0.3063(4) 0.0489(12) Uani 1 1 d . . . . . C8 C 0.30174(16) 0.44724(16) 0.5205(4) 0.0271(9) Uani 1 1 d . . . . . N8 N 0.26810(14) 0.43362(15) 0.5749(3) 0.0358(9) Uani 1 1 d . . . . . K1 K 0.15934(4) 0.45492(4) 0.56003(8) 0.0327(3) Uani 1 1 d . . . . . K2 K 0.37921(5) 0.36032(5) 1.09457(11) 0.0543(4) Uani 1 1 d . . . . . O1 O 0.4722(2) 0.3183(3) 1.1073(7) 0.138(3) Uani 1 1 d . . . . . C12 C 0.5190(4) 0.3173(4) 1.1200(13) 0.149(5) Uani 1 1 d . . . . . C13 C 0.5524(4) 0.3106(5) 1.0066(14) 0.229(9) Uani 1 1 d . . . . . H13A H 0.5807 0.2852 1.0180 0.343 Uiso 1 1 calc R U . . . H13B H 0.5674 0.3445 0.9855 0.343 Uiso 1 1 calc R U . . . H13C H 0.5292 0.2981 0.9481 0.343 Uiso 1 1 calc R U . . . C14 C 0.5406(7) 0.3144(6) 1.2358(15) 0.286(13) Uani 1 1 d . . . . . H14A H 0.5790 0.3132 1.2331 0.429 Uiso 1 1 calc R U . . . H14B H 0.5274 0.2828 1.2720 0.429 Uiso 1 1 calc R U . . . H14C H 0.5295 0.3454 1.2772 0.429 Uiso 1 1 calc R U . . . 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 N1 0.0155(16) 0.0274(18) 0.0211(17) 0.0016(14) 0.0026(13) 0.0026(14) C1 0.019(2) 0.027(2) 0.031(2) 0.0014(18) 0.0085(17) 0.0002(17) F1 0.0330(14) 0.0417(16) 0.0444(16) 0.0062(13) 0.0065(12) -0.0146(12) C2 0.017(2) 0.040(3) 0.027(2) -0.0106(19) -0.0029(17) 0.0032(18) F2 0.0302(15) 0.072(2) 0.0463(17) -0.0132(15) -0.0115(13) -0.0071(14) C3 0.031(2) 0.036(2) 0.020(2) -0.0021(18) -0.0011(18) 0.0114(19) B2 0.014(4) 0.048(4) 0.023(3) 0.000(3) -0.006(4) 0.005(4) C9 0.028(3) 0.057(4) 0.017(3) 0.009(3) -0.002(2) 0.017(3) N9 0.045(3) 0.069(4) 0.028(3) 0.023(3) 0.003(3) 0.013(3) C10 0.031(3) 0.066(5) 0.016(3) 0.006(3) 0.000(2) 0.000(3) N10 0.070(5) 0.071(4) 0.030(3) -0.010(3) 0.011(3) 0.000(4) C11 0.023(4) 0.090(6) 0.018(3) 0.009(3) -0.001(2) 0.009(4) N11 0.026(3) 0.130(7) 0.038(3) 0.013(4) -0.005(3) 0.016(3) B20 0.014(4) 0.048(4) 0.023(3) 0.000(3) -0.006(4) 0.005(4) C20 0.033(11) 0.031(10) 0.024(9) -0.007(8) -0.015(8) 0.013(8) N20 0.019(8) 0.059(11) 0.028(8) 0.009(8) -0.014(7) 0.005(7) C21 0.023(9) 0.076(14) 0.013(8) -0.009(9) -0.002(7) 0.017(9) N21 0.042(10) 0.112(15) 0.042(10) -0.010(10) -0.003(9) 0.024(10) C22 0.043(11) 0.043(12) 0.014(8) 0.007(8) -0.003(8) 0.002(9) N22 0.11(2) 0.056(14) 0.043(12) 0.013(10) -0.024(12) 0.006(13) C4 0.029(2) 0.025(2) 0.020(2) 0.0010(16) 0.0054(17) 0.0061(18) F4 0.0530(17) 0.0281(13) 0.0287(13) 0.0108(11) 0.0067(12) -0.0007(12) C5 0.0170(19) 0.025(2) 0.0170(19) -0.0011(16) 0.0045(15) 0.0054(16) B1 0.023(2) 0.028(2) 0.025(2) -0.002(2) 0.0024(19) -0.0044(19) C6 0.021(2) 0.049(3) 0.055(3) -0.023(3) 0.006(2) -0.011(2) N6 0.030(2) 0.078(4) 0.108(5) -0.062(4) 0.006(3) -0.008(2) C7 0.020(2) 0.050(3) 0.025(2) 0.001(2) -0.0033(18) -0.012(2) N7 0.032(2) 0.074(3) 0.040(2) 0.025(2) -0.0159(19) -0.015(2) C8 0.024(2) 0.027(2) 0.030(2) 0.0028(18) 0.0022(18) 0.0029(18) N8 0.025(2) 0.044(2) 0.038(2) 0.0141(18) 0.0073(17) 0.0015(18) K1 0.0239(5) 0.0457(6) 0.0285(5) -0.0006(4) 0.0077(4) 0.0027(4) K2 0.0444(7) 0.0647(8) 0.0539(7) 0.0180(6) 0.0125(6) 0.0089(6) O1 0.060(4) 0.122(5) 0.232(9) 0.010(5) 0.007(5) 0.019(4) C12 0.062(6) 0.129(9) 0.257(16) 0.041(10) 0.022(8) 0.017(6) C13 0.112(9) 0.200(14) 0.37(2) -0.130(15) 0.137(12) -0.034(9) C14 0.32(2) 0.221(17) 0.31(2) -0.095(16) -0.23(2) 0.134(16) 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' O O 0.0106 0.0060 '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' 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 C1 N1 C5 117.8(3) . . C1 N1 K2 96.8(2) . 3_554 C5 N1 K2 135.7(2) . 3_554 N1 C1 F1 116.3(4) . . N1 C1 C2 125.1(4) . . F1 C1 C2 118.7(4) . . N1 C1 K2 60.9(2) . 3_554 F1 C1 K2 61.6(2) . 3_554 C2 C1 K2 154.0(3) . 3_554 C1 F1 K2 95.0(2) . 3_554 F2 C2 C3 120.8(4) . . F2 C2 C1 118.9(4) . . C3 C2 C1 120.3(4) . . C2 C3 C4 113.3(4) . . C2 C3 B2 122.4(5) . . C4 C3 B2 124.1(5) . . C2 C3 B20 111.9(10) . . C4 C3 B20 133.2(11) . . C10 B2 C11 110.9(6) . . C10 B2 C9 104.9(6) . . C11 B2 C9 108.4(6) . . C10 B2 C3 108.6(5) . . C11 B2 C3 107.5(5) . . C9 B2 C3 116.7(5) . . N9 C9 B2 176.8(7) . . C9 N9 K2 144.7(5) . . C9 N9 K1 108.9(4) . 3 K2 N9 K1 96.21(18) . 3 N10 C10 B2 175.4(7) . . C10 N10 K1 110.6(5) . 2_565 N11 C11 B2 177.8(9) . . C11 N11 K1 142.6(6) . 10_657 C11 N11 K2 123.2(6) . 11_667 K1 N11 K2 93.47(17) 10_657 11_667 C22 B20 C21 103(2) . . C22 B20 C20 109.1(19) . . C21 B20 C20 113(2) . . C22 B20 C3 107.4(18) . . C21 B20 C3 103.2(15) . . C20 B20 C3 120(2) . . N20 C20 B20 175(2) . . C20 N20 K1 116.7(14) . 10_657 C20 N20 K2 138.8(14) . 9_667 K1 N20 K2 103.8(4) 10_657 9_667 N21 C21 B20 177(2) . . C21 N21 K1 136(2) . 2_565 N22 C22 B20 177(2) . . N22 C22 K2 52.6(16) . 11_667 B20 C22 K2 125.8(14) . 11_667 C22 N22 K2 109.0(18) . 11_667 F4 C4 C5 116.9(4) . . F4 C4 C3 118.0(4) . . C5 C4 C3 125.1(4) . . C4 F4 K1 137.6(2) . 3 N1 C5 C4 118.4(4) . . N1 C5 B1 116.9(3) . . C4 C5 B1 124.7(4) . . C6 B1 C7 108.0(4) . . C6 B1 C8 107.9(4) . . C7 B1 C8 107.8(3) . . C6 B1 C5 111.7(4) . . C7 B1 C5 108.9(3) . . C8 B1 C5 112.5(3) . . N6 C6 B1 179.6(7) . . C6 N6 K2 134.3(5) . 1_554 N7 C7 B1 178.2(5) . . N7 C7 K2 60.5(3) . 3_554 B1 C7 K2 118.4(3) . 3_554 C7 N7 K1 128.4(4) . 4_454 C7 N7 K2 100.5(3) . 3_554 K1 N7 K2 107.42(16) 4_454 3_554 C7 N7 K1 120.2(4) . 2_564 K1 N7 K1 103.70(12) 4_454 2_564 K2 N7 K1 87.69(11) 3_554 2_564 N8 C8 B1 179.5(5) . . C8 N8 K1 130.0(3) . . C8 N8 K1 116.4(3) . 3 K1 N8 K1 108.89(12) . 3 N8 K1 N11 140.78(15) . 10_557 N8 K1 N21 141.2(4) . 2_564 N8 K1 N7 76.32(12) . 3 N11 K1 N7 112.44(19) 10_557 3 N21 K1 N7 72.3(5) 2_564 3 N8 K1 N9 80.65(15) . 4_454 N11 K1 N9 75.1(2) 10_557 4_454 N7 K1 N9 150.24(15) 3 4_454 N8 K1 N20 142.3(3) . 10_557 N21 K1 N20 46.0(5) 2_564 10_557 N7 K1 N20 75.0(3) 3 10_557 N8 K1 N8 84.44(11) . 4_454 N11 K1 N8 134.76(15) 10_557 4_454 N21 K1 N8 64.5(4) 2_564 4_454 N7 K1 N8 72.03(11) 3 4_454 N9 K1 N8 124.32(13) 4_454 4_454 N20 K1 N8 109.0(3) 10_557 4_454 N8 K1 F4 72.65(10) . 4_454 N11 K1 F4 118.46(16) 10_557 4_454 N21 K1 F4 109.8(5) 2_564 4_454 N7 K1 F4 127.55(11) 3 4_454 N9 K1 F4 60.48(11) 4_454 4_454 N20 K1 F4 145.1(3) 10_557 4_454 N8 K1 F4 63.86(9) 4_454 4_454 N8 K1 N10 145.82(16) . 2_564 N11 K1 N10 64.25(17) 10_557 2_564 N7 K1 N10 120.89(15) 3 2_564 N9 K1 N10 88.62(18) 4_454 2_564 N8 K1 N10 75.05(14) 4_454 2_564 F4 K1 N10 73.82(14) 4_454 2_564 N8 K1 N7 72.11(11) . 2_565 N11 K1 N7 71.20(14) 10_557 2_565 N21 K1 N7 125.2(4) 2_564 2_565 N7 K1 N7 83.48(12) 3 2_565 N9 K1 N7 71.59(14) 4_454 2_565 N20 K1 N7 80.7(3) 10_557 2_565 N8 K1 N7 149.53(11) 4_454 2_565 F4 K1 N7 123.72(11) 4_454 2_565 N10 K1 N7 134.60(14) 2_564 2_565 N8 K1 K2 97.97(8) . 4_454 N11 K1 K2 44.99(15) 10_557 4_454 N21 K1 K2 119.0(4) 2_564 4_454 N7 K1 K2 126.32(9) 3 4_454 N9 K1 K2 39.33(10) 4_454 4_454 N20 K1 K2 80.1(3) 10_557 4_454 N8 K1 K2 161.60(8) 4_454 4_454 F4 K1 K2 99.30(6) 4_454 4_454 N10 K1 K2 93.73(12) 2_564 4_454 N7 K1 K2 45.64(8) 2_565 4_454 N8 K1 K1 36.81(8) . 3 N11 K1 K1 104.16(13) 10_557 3 N21 K1 K1 154.7(5) 2_564 3 N7 K1 K1 85.76(8) 3 3 N9 K1 K1 64.57(13) 4_454 3 N20 K1 K1 116.8(3) 10_557 3 N8 K1 K1 121.05(8) 4_454 3 F4 K1 K1 93.41(6) 4_454 3 N10 K1 K1 153.10(13) 2_564 3 N7 K1 K1 36.94(8) 2_565 3 K2 K1 K1 64.50(3) 4_454 3 O1 K2 N9 90.2(2) . . O1 K2 N6 90.6(2) . 1_556 N9 K2 N6 139.73(19) . 1_556 O1 K2 N22 73.1(5) . 16_657 N6 K2 N22 130.7(4) 1_556 16_657 O1 K2 N1 126.82(18) . 4_455 N9 K2 N1 139.17(14) . 4_455 N6 K2 N1 65.12(11) 1_556 4_455 N22 K2 N1 87.9(4) 16_657 4_455 O1 K2 F1 83.59(17) . 4_455 N9 K2 F1 150.64(16) . 4_455 N6 K2 F1 69.24(13) 1_556 4_455 N22 K2 F1 63.0(4) 16_657 4_455 N1 K2 F1 44.29(8) 4_455 4_455 O1 K2 N11 120.7(2) . 16_657 N9 K2 N11 76.48(18) . 16_657 N6 K2 N11 135.00(16) 1_556 16_657 N1 K2 N11 70.09(14) 4_455 16_657 F1 K2 N11 82.11(12) 4_455 16_657 O1 K2 N7 161.03(18) . 4_455 N9 K2 N7 76.29(14) . 4_455 N6 K2 N7 91.30(14) 1_556 4_455 N22 K2 N7 118.8(5) 16_657 4_455 N1 K2 N7 70.60(10) 4_455 4_455 F1 K2 N7 114.65(10) 4_455 4_455 N11 K2 N7 69.55(16) 16_657 4_455 O1 K2 N20 91.7(3) . 9_667 N6 K2 N20 67.1(3) 1_556 9_667 N22 K2 N20 155.2(5) 16_657 9_667 N1 K2 N20 116.9(3) 4_455 9_667 F1 K2 N20 136.0(3) 4_455 9_667 N7 K2 N20 71.8(3) 4_455 9_667 O1 K2 C1 104.49(18) . 4_455 N9 K2 C1 156.85(16) . 4_455 N6 K2 C1 59.28(13) 1_556 4_455 N22 K2 C1 79.9(4) 16_657 4_455 N1 K2 C1 22.34(9) 4_455 4_455 F1 K2 C1 23.44(8) 4_455 4_455 N11 K2 C1 80.62(14) 16_657 4_455 N7 K2 C1 92.64(11) 4_455 4_455 N20 K2 C1 123.6(3) 9_667 4_455 O1 K2 C22 90.7(4) . 16_657 N6 K2 C22 127.4(3) 1_556 16_657 N22 K2 C22 18.4(5) 16_657 16_657 N1 K2 C22 72.6(3) 4_455 16_657 F1 K2 C22 58.7(3) 4_455 16_657 N7 K2 C22 103.1(4) 4_455 16_657 N20 K2 C22 165.3(4) 9_667 16_657 C1 K2 C22 69.6(3) 4_455 16_657 O1 K2 C7 172.0(2) . 4_455 N9 K2 C7 94.12(14) . 4_455 N6 K2 C7 81.77(13) 1_556 4_455 N22 K2 C7 113.8(5) 16_657 4_455 N1 K2 C7 51.60(10) 4_455 4_455 F1 K2 C7 95.77(9) 4_455 4_455 N11 K2 C7 66.99(16) 16_657 4_455 N7 K2 C7 19.04(10) 4_455 4_455 N20 K2 C7 83.2(3) 9_667 4_455 C1 K2 C7 73.60(11) 4_455 4_455 C22 K2 C7 95.8(4) 16_657 4_455 C12 O1 K2 156.6(8) . . O1 C12 C14 118.8(14) . . O1 C12 C13 114.3(14) . . C14 C12 C13 126.3(11) . . C12 C13 H13A 109.5 . . C12 C13 H13B 109.5 . . H13A C13 H13B 109.5 . . C12 C13 H13C 109.5 . . H13A C13 H13C 109.5 . . H13B C13 H13C 109.5 . . C12 C14 H14A 109.5 . . C12 C14 H14B 109.5 . . H14A C14 H14B 109.5 . . C12 C14 H14C 109.5 . . H14A C14 H14C 109.5 . . H14B C14 H14C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C1 1.296(5) . N1 C5 1.352(5) . N1 K2 2.978(3) 3_554 C1 F1 1.352(5) . C1 C2 1.378(6) . C1 K2 3.386(4) 3_554 F1 K2 2.988(3) 3_554 C2 F2 1.328(5) . C2 C3 1.368(6) . C3 C4 1.385(6) . C3 B2 1.625(8) . C3 B20 1.73(3) . B2 C10 1.577(11) . B2 C11 1.589(9) . B2 C9 1.600(11) . C9 N9 1.152(8) . N9 K2 2.720(5) . N9 K1 3.006(6) 3 C10 N10 1.151(9) . N10 K1 3.067(6) 2_565 C11 N11 1.145(8) . N11 K1 2.834(6) 10_657 N11 K2 3.022(7) 11_667 B20 C22 1.58(4) . B20 C21 1.59(3) . B20 C20 1.59(3) . C20 N20 1.13(2) . N20 K1 3.011(15) 10_657 N20 K2 3.129(17) 9_667 C21 N21 1.14(3) . N21 K1 2.86(2) 2_565 C22 N22 1.14(3) . C22 K2 3.41(2) 11_667 N22 K2 2.87(3) 11_667 C4 F4 1.366(5) . C4 C5 1.374(5) . F4 K1 3.063(3) 3 C5 B1 1.626(6) . B1 C6 1.590(7) . B1 C7 1.597(7) . B1 C8 1.601(6) . C6 N6 1.136(6) . N6 K2 2.828(6) 1_554 C7 N7 1.145(6) . C7 K2 3.450(5) 3_554 N7 K1 2.943(5) 4_454 N7 K2 3.053(4) 3_554 N7 K1 3.106(5) 2_564 C8 N8 1.138(5) . N8 K1 2.833(4) . N8 K1 3.013(4) 3 K1 N11 2.834(6) 10_557 K1 N21 2.86(2) 2_564 K1 N7 2.943(5) 3 K1 N9 3.006(6) 4_454 K1 N20 3.011(15) 10_557 K1 N8 3.013(4) 4_454 K1 F4 3.063(3) 4_454 K1 N10 3.067(6) 2_564 K1 N7 3.106(5) 2_565 K1 K2 4.2667(16) 4_454 K1 K1 4.7576(11) 3 K2 O1 2.608(6) . K2 N6 2.828(6) 1_556 K2 N22 2.87(3) 16_657 K2 N1 2.978(3) 4_455 K2 F1 2.989(3) 4_455 K2 N11 3.022(7) 16_657 K2 N7 3.053(4) 4_455 K2 N20 3.129(17) 9_667 K2 C1 3.386(4) 4_455 K2 C22 3.41(2) 16_657 K2 C7 3.450(5) 4_455 O1 C12 1.204(10) . C12 C14 1.518(19) . C12 C13 1.634(17) . C13 H13A 0.9800 . C13 H13B 0.9800 . C13 H13C 0.9800 . C14 H14A 0.9800 . C14 H14B 0.9800 . C14 H14C 0.9800 .