#------------------------------------------------------------------------------ #$Date: 2017-06-27 04:13:01 +0300 (Tue, 27 Jun 2017) $ #$Revision: 198148 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/63/1546385.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_1546385 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 'C26 H16 B2 F8 K2 N6 O2' _chemical_formula_sum 'C26 H16 B2 F8 K2 N6 O2' _chemical_formula_weight 696.27 _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_space_group_name_H-M 'C 1 2 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 94.050(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 28.487(4) _cell_length_b 12.3676(16) _cell_length_c 8.8225(11) _cell_measurement_reflns_used 7750 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.34 _cell_measurement_theta_min 2.31 _cell_volume 3100.5(7) _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 0.998 _diffrn_measurement_device_type 'Bruker X8-APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_unetI/netI 0.0395 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 21628 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 26.785 _diffrn_reflns_theta_min 1.433 _diffrn_source 'rotating-anode (Nonius FR-591)' _exptl_absorpt_coefficient_mu 0.389 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.7003 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SadAbs 2014/5 (Bruker AXS)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.492 _exptl_crystal_description plate _exptl_crystal_F_000 1400 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.272 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details ; Flack x determined using 2562 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.005(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 415 _refine_ls_number_reflns 6608 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0301 _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^)+(0.0269P)^2^+0.5359P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.0611 _reflns_Friedel_coverage 0.906 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.995 _reflns_number_gt 5996 _reflns_number_total 6608 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7sc02249b2.cif _cod_data_source_block JL027_JL_KBP2thf _cod_original_cell_volume 3100.6(7) _cod_database_code 1546385 _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 0.926 _shelx_estimated_absorpt_t_max 0.981 _shelx_res_file ; fertig_a.res created by SHELXL-2014/7 TITL fertig_a.res in C2 REM Old TITL fertig in C2 REM SHELXT solution in C2 REM R1 0.062, Rweak 0.032, Alpha 0.001, Orientation as input REM Flack x = 0.009 ( 0.013 ) from Parsons' quotients REM Formula found by SHELXT: C26 B2 N7 O F8 K2 CELL 0.71073 28.4875 12.3676 8.8225 90.000 94.050 90.000 ZERR 4.000 0.0036 0.0016 0.0011 0.000 0.005 0.000 LATT -7 SYMM -X, Y, -Z SFAC C H B N O F K UNIT 104 64 8 24 8 32 8 TEMP -173 SIZE 0.05 0.10 0.20 L.S. 10 BOND $H ACTA 52 LIST 4 FMAP 2 PLAN 20 WGHT 0.026900 0.535900 FVAR 0.41782 K1 7 0.321376 0.830837 0.995311 11.00000 0.01790 0.01575 = 0.02754 -0.00026 0.00265 -0.00147 N1 4 0.731013 0.370856 0.839563 11.00000 0.01810 0.01993 = 0.02673 0.00028 0.00150 0.00032 O1 5 0.335232 0.921714 0.720831 11.00000 0.02086 0.03239 = 0.02378 -0.00180 0.00454 0.00068 C1 1 0.701043 0.314764 0.796841 11.00000 0.01510 0.01737 = 0.01797 0.00181 0.00408 0.00371 B1 3 0.662147 0.229155 0.734775 11.00000 0.01452 0.01565 = 0.01575 -0.00024 0.00156 0.00105 O2 5 0.415134 0.821296 1.050824 11.00000 0.02687 0.02879 = 0.06366 -0.00190 -0.00796 0.00423 K2 7 0.229793 0.587167 0.206053 11.00000 0.01956 0.01580 = 0.01513 -0.00017 0.00159 0.00055 N2 4 0.676797 0.045901 0.907800 11.00000 0.02234 0.01795 = 0.02044 0.00191 -0.00023 0.00199 C2 1 0.670828 0.120889 0.834592 11.00000 0.01164 0.01965 = 0.01284 -0.00452 0.00131 0.00011 B2 3 0.309671 0.460680 0.746955 11.00000 0.01540 0.01467 = 0.01931 -0.00034 0.00216 0.00118 C4 1 0.303769 0.550733 0.874306 11.00000 0.01371 0.01693 = 0.02361 0.00326 0.00250 0.00050 N4 4 0.299952 0.614315 0.966465 11.00000 0.03113 0.01831 = 0.02978 -0.00388 0.00758 -0.00084 C3 1 0.671728 0.201881 0.563410 11.00000 0.01490 0.01648 = 0.01842 0.00224 0.00112 0.00243 N3 4 0.678317 0.181725 0.440386 11.00000 0.02712 0.02741 = 0.02272 -0.00017 0.00674 0.00027 C5 1 0.296247 0.514032 0.583886 11.00000 0.01597 0.02201 = 0.02476 0.00108 -0.00109 0.00092 N5 4 0.285936 0.549616 0.467354 11.00000 0.02940 0.03688 = 0.03111 0.00634 -0.00790 -0.00032 C6 1 0.271141 0.369209 0.767349 11.00000 0.01766 0.01647 = 0.01704 -0.00241 0.00158 0.00458 N6 4 0.241682 0.308214 0.778679 11.00000 0.01920 0.02032 = 0.02558 -0.00070 0.00440 0.00228 C11 1 0.607929 0.267423 0.745979 11.00000 0.01452 0.01994 = 0.01251 0.00398 -0.00013 0.00169 C12 1 0.593192 0.363365 0.806764 11.00000 0.01379 0.01724 = 0.01523 0.00126 -0.00121 -0.00205 F12 6 0.624804 0.437470 0.861290 11.00000 0.01612 0.01915 = 0.03108 -0.00542 0.00115 -0.00105 C14 1 0.510375 0.320175 0.763781 11.00000 0.01494 0.02168 = 0.01710 0.00180 0.00185 0.00148 C13 1 0.546189 0.389340 0.816602 11.00000 0.01917 0.01572 = 0.01899 -0.00138 0.00490 0.00301 F13 6 0.535455 0.483486 0.881140 11.00000 0.02091 0.01951 = 0.03573 -0.00768 0.00566 0.00303 C15 1 0.524396 0.222359 0.704183 11.00000 0.01681 0.02224 = 0.01609 -0.00356 -0.00074 -0.00205 F15 6 0.491827 0.150571 0.651711 11.00000 0.01583 0.02951 = 0.02945 -0.01274 0.00047 -0.00500 C16 1 0.571508 0.198254 0.694999 11.00000 0.02018 0.01590 = 0.01596 -0.00339 0.00231 0.00140 F16 6 0.582261 0.102521 0.632857 11.00000 0.01885 0.01994 = 0.03177 -0.01118 0.00206 0.00088 C17 1 0.460228 0.351817 0.763412 11.00000 0.01428 0.02493 = 0.01524 -0.00265 0.00025 0.00024 C19 1 0.398477 0.481047 0.697962 11.00000 0.02003 0.01962 = 0.02312 0.00476 -0.00085 0.00415 F19 6 0.387585 0.578833 0.637387 11.00000 0.02115 0.02104 = 0.05007 0.01683 0.00183 0.00113 C18 1 0.444804 0.448845 0.698068 11.00000 0.01509 0.02563 = 0.02350 0.00435 0.00505 -0.00302 F18 6 0.475397 0.513472 0.632700 11.00000 0.01856 0.03541 = 0.04194 0.01698 0.00594 -0.00224 C20 1 0.363846 0.418213 0.756483 11.00000 0.01402 0.01651 = 0.01630 -0.00306 -0.00011 0.00048 C21 1 0.379712 0.321433 0.822032 11.00000 0.01561 0.01923 = 0.01371 -0.00135 0.00410 -0.00117 F21 6 0.349454 0.255852 0.889253 11.00000 0.01666 0.02194 = 0.02271 0.00519 0.00371 -0.00192 C22 1 0.426186 0.289289 0.826095 11.00000 0.01926 0.01658 = 0.01245 0.00049 -0.00228 0.00270 F22 6 0.438519 0.195806 0.896283 11.00000 0.02086 0.01956 = 0.02687 0.00605 0.00023 0.00418 C30 1 0.438392 0.907875 1.133560 11.00000 0.03736 0.03553 = 0.04724 -0.00459 -0.00423 0.00362 AFIX 23 H30A 2 0.417112 0.940464 1.204911 11.00000 -1.20000 H30B 2 0.447854 0.964720 1.062829 11.00000 -1.20000 AFIX 0 C31 1 0.481003 0.860833 1.219390 11.00000 0.03294 0.05891 = 0.04416 -0.00470 -0.00286 0.00482 AFIX 23 H31A 2 0.488185 0.898810 1.317061 11.00000 -1.20000 H31B 2 0.508908 0.863611 1.158680 11.00000 -1.20000 AFIX 0 C32 1 0.465336 0.744355 1.244563 11.00000 0.04893 0.06112 = 0.05899 0.01009 0.00638 0.02305 AFIX 23 H32A 2 0.492665 0.694965 1.257854 11.00000 -1.20000 H32B 2 0.446455 0.738694 1.334227 11.00000 -1.20000 AFIX 0 C33 1 0.435873 0.720205 1.099203 11.00000 0.03350 0.03373 = 0.07172 0.00571 0.00549 0.01001 AFIX 23 H33A 2 0.455769 0.691292 1.021022 11.00000 -1.20000 H33B 2 0.411164 0.666460 1.117691 11.00000 -1.20000 AFIX 0 C40 1 0.383295 0.952889 0.699391 11.00000 0.02150 0.03440 = 0.03335 0.00683 0.00223 -0.00202 AFIX 23 H40A 2 0.403036 0.946974 0.795981 11.00000 -1.20000 H40B 2 0.384628 1.028283 0.662235 11.00000 -1.20000 AFIX 0 C41 1 0.400053 0.874784 0.582177 11.00000 0.02422 0.04931 = 0.03604 0.00286 0.00588 0.00624 AFIX 23 H41A 2 0.411994 0.806833 0.630056 11.00000 -1.20000 H41B 2 0.424949 0.907417 0.524066 11.00000 -1.20000 AFIX 0 C42 1 0.355286 0.855584 0.481910 11.00000 0.03172 0.05835 = 0.02662 -0.00654 0.00456 0.00189 AFIX 23 H42A 2 0.349895 0.914256 0.406346 11.00000 -1.20000 H42B 2 0.356426 0.785492 0.428097 11.00000 -1.20000 AFIX 0 C43 1 0.318057 0.855234 0.593543 11.00000 0.02767 0.05836 = 0.03229 -0.01998 -0.00029 0.00179 AFIX 23 H43A 2 0.288280 0.885102 0.546253 11.00000 -1.20000 H43B 2 0.312166 0.780562 0.627902 11.00000 -1.20000 AFIX 0 HKLF 4 REM fertig_a.res in C2 REM R1 = 0.0301 for 5996 Fo > 4sig(Fo) and 0.0368 for all 6608 data REM 415 parameters refined using 1 restraints END WGHT 0.0269 0.5360 REM Highest difference peak 0.272, deepest hole -0.172, 1-sigma level 0.042 Q1 1 0.6310 0.2520 0.7455 11.00000 0.05 0.27 Q2 1 0.4873 0.3370 0.7560 11.00000 0.05 0.19 Q3 1 0.2376 0.5852 0.0898 11.00000 0.05 0.19 Q4 1 0.4215 0.4672 0.7334 11.00000 0.05 0.18 Q5 1 0.3505 0.6431 0.4502 11.00000 0.05 0.18 Q6 1 0.6701 0.1817 0.7828 11.00000 0.05 0.18 Q7 1 0.6608 0.1037 0.9140 11.00000 0.05 0.17 Q8 1 0.4185 0.4470 0.6579 11.00000 0.05 0.17 Q9 1 0.5146 0.2863 0.7153 11.00000 0.05 0.17 Q10 1 0.2915 0.4194 0.7510 11.00000 0.05 0.17 Q11 1 0.6636 0.2387 0.6359 11.00000 0.05 0.17 Q12 1 0.5935 0.2287 0.7437 11.00000 0.05 0.17 Q13 1 0.5276 0.3572 0.7558 11.00000 0.05 0.16 Q14 1 0.4595 0.2611 0.5300 11.00000 0.05 0.16 Q15 1 0.6937 0.1063 0.8897 11.00000 0.05 0.16 Q16 1 0.3345 0.4542 0.7445 11.00000 0.05 0.16 Q17 1 0.4039 0.3166 0.8550 11.00000 0.05 0.16 Q18 1 0.5690 0.3787 0.7846 11.00000 0.05 0.16 Q19 1 0.4419 0.3818 0.6535 11.00000 0.05 0.16 Q20 1 0.2382 0.5401 0.2873 11.00000 0.05 0.15 ; _shelx_res_checksum 54425 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp K1 K 0.32138(2) 0.83084(5) 0.99531(7) 0.02035(14) Uani 1 1 d . . N1 N 0.73101(8) 0.37086(19) 0.8396(3) 0.0216(5) Uani 1 1 d . . O1 O 0.33523(7) 0.92171(17) 0.7208(2) 0.0255(5) Uani 1 1 d . . C1 C 0.70104(9) 0.3148(2) 0.7968(3) 0.0167(6) Uani 1 1 d . . B1 B 0.66215(10) 0.2292(3) 0.7348(4) 0.0153(6) Uani 1 1 d . . O2 O 0.41513(7) 0.82130(19) 1.0508(3) 0.0403(6) Uani 1 1 d . . K2 K 0.22979(2) 0.58717(4) 0.20605(6) 0.01681(13) Uani 1 1 d . . N2 N 0.67680(8) 0.04590(19) 0.9078(3) 0.0203(5) Uani 1 1 d . . C2 C 0.67083(9) 0.1209(2) 0.8346(3) 0.0147(6) Uani 1 1 d . . B2 B 0.30967(10) 0.4607(3) 0.7470(4) 0.0164(6) Uani 1 1 d . . C4 C 0.30377(9) 0.5507(2) 0.8743(3) 0.0180(6) Uani 1 1 d . . N4 N 0.29995(9) 0.6143(2) 0.9665(3) 0.0261(6) Uani 1 1 d . . C3 C 0.67173(9) 0.2019(2) 0.5634(3) 0.0166(6) Uani 1 1 d . . N3 N 0.67832(9) 0.1817(2) 0.4404(3) 0.0255(6) Uani 1 1 d . . C5 C 0.29625(10) 0.5140(2) 0.5839(4) 0.0210(6) Uani 1 1 d . . N5 N 0.28594(9) 0.5496(2) 0.4674(3) 0.0329(7) Uani 1 1 d . . C6 C 0.27114(10) 0.3692(2) 0.7673(3) 0.0170(6) Uani 1 1 d . . N6 N 0.24168(8) 0.30821(19) 0.7787(3) 0.0216(6) Uani 1 1 d . . C11 C 0.60793(9) 0.2674(2) 0.7460(3) 0.0157(6) Uani 1 1 d . . C12 C 0.59319(9) 0.3634(2) 0.8068(3) 0.0155(6) Uani 1 1 d . . F12 F 0.62480(5) 0.43747(13) 0.86129(19) 0.0221(4) Uani 1 1 d . . C14 C 0.51038(9) 0.3202(2) 0.7638(3) 0.0179(6) Uani 1 1 d . . C13 C 0.54619(10) 0.3893(2) 0.8166(3) 0.0178(6) Uani 1 1 d . . F13 F 0.53545(5) 0.48349(13) 0.88114(19) 0.0252(4) Uani 1 1 d . . C15 C 0.52440(9) 0.2224(2) 0.7042(3) 0.0185(6) Uani 1 1 d . . F15 F 0.49183(5) 0.15057(13) 0.6517(2) 0.0250(4) Uani 1 1 d . . C16 C 0.57151(10) 0.1983(2) 0.6950(3) 0.0173(6) Uani 1 1 d . . F16 F 0.58226(5) 0.10252(13) 0.63286(18) 0.0235(4) Uani 1 1 d . . C17 C 0.46023(9) 0.3518(2) 0.7634(3) 0.0182(6) Uani 1 1 d . . C19 C 0.39848(10) 0.4810(2) 0.6980(3) 0.0210(6) Uani 1 1 d . . F19 F 0.38758(5) 0.57883(14) 0.6374(2) 0.0308(4) Uani 1 1 d . . C18 C 0.44480(9) 0.4488(2) 0.6981(3) 0.0212(6) Uani 1 1 d . . F18 F 0.47540(6) 0.51347(15) 0.6327(2) 0.0318(4) Uani 1 1 d . . C20 C 0.36385(9) 0.4182(2) 0.7565(3) 0.0157(6) Uani 1 1 d . . C21 C 0.37971(9) 0.3214(2) 0.8220(3) 0.0160(6) Uani 1 1 d . . F21 F 0.34945(5) 0.25585(12) 0.88925(18) 0.0203(4) Uani 1 1 d . . C22 C 0.42619(10) 0.2893(2) 0.8261(3) 0.0163(6) Uani 1 1 d . . F22 F 0.43852(6) 0.19581(13) 0.89628(19) 0.0225(4) Uani 1 1 d . . C30 C 0.43839(13) 0.9079(3) 1.1336(4) 0.0404(9) Uani 1 1 d . . H30A H 0.4171 0.9405 1.2049 0.048 Uiso 1 1 calc R U H30B H 0.4479 0.9647 1.0628 0.048 Uiso 1 1 calc R U C31 C 0.48100(13) 0.8608(3) 1.2194(5) 0.0456(10) Uani 1 1 d . . H31A H 0.4882 0.8988 1.3171 0.055 Uiso 1 1 calc R U H31B H 0.5089 0.8636 1.1587 0.055 Uiso 1 1 calc R U C32 C 0.46534(14) 0.7444(3) 1.2446(5) 0.0562(12) Uani 1 1 d . . H32A H 0.4927 0.6950 1.2579 0.067 Uiso 1 1 calc R U H32B H 0.4465 0.7387 1.3342 0.067 Uiso 1 1 calc R U C33 C 0.43587(13) 0.7202(3) 1.0992(5) 0.0462(10) Uani 1 1 d . . H33A H 0.4558 0.6913 1.0210 0.055 Uiso 1 1 calc R U H33B H 0.4112 0.6665 1.1177 0.055 Uiso 1 1 calc R U C40 C 0.38330(10) 0.9529(3) 0.6994(4) 0.0297(7) Uani 1 1 d . . H40A H 0.4030 0.9470 0.7960 0.036 Uiso 1 1 calc R U H40B H 0.3846 1.0283 0.6622 0.036 Uiso 1 1 calc R U C41 C 0.40005(11) 0.8748(3) 0.5822(4) 0.0363(8) Uani 1 1 d . . H41A H 0.4120 0.8068 0.6301 0.044 Uiso 1 1 calc R U H41B H 0.4249 0.9074 0.5241 0.044 Uiso 1 1 calc R U C42 C 0.35529(11) 0.8556(3) 0.4819(4) 0.0388(9) Uani 1 1 d . . H42A H 0.3499 0.9143 0.4063 0.047 Uiso 1 1 calc R U H42B H 0.3564 0.7855 0.4281 0.047 Uiso 1 1 calc R U C43 C 0.31806(11) 0.8552(3) 0.5935(4) 0.0396(9) Uani 1 1 d . . H43A H 0.2883 0.8851 0.5463 0.047 Uiso 1 1 calc R U H43B H 0.3122 0.7806 0.6279 0.047 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 K1 0.0179(3) 0.0157(3) 0.0275(4) -0.0003(3) 0.0026(3) -0.0015(2) N1 0.0181(12) 0.0199(13) 0.0267(14) 0.0003(11) 0.0015(11) 0.0003(10) O1 0.0209(10) 0.0324(12) 0.0238(11) -0.0018(9) 0.0045(9) 0.0007(9) C1 0.0151(13) 0.0174(15) 0.0180(14) 0.0018(11) 0.0041(12) 0.0037(11) B1 0.0145(15) 0.0156(16) 0.0157(16) -0.0002(12) 0.0016(12) 0.0011(13) O2 0.0269(11) 0.0288(13) 0.0637(17) -0.0019(13) -0.0080(11) 0.0042(11) K2 0.0196(3) 0.0158(3) 0.0151(3) -0.0002(2) 0.0016(2) 0.0005(2) N2 0.0223(12) 0.0179(13) 0.0204(13) 0.0019(11) -0.0002(11) 0.0020(10) C2 0.0116(13) 0.0196(15) 0.0128(14) -0.0045(11) 0.0013(11) 0.0001(10) B2 0.0154(15) 0.0147(16) 0.0193(17) -0.0003(12) 0.0022(13) 0.0012(12) C4 0.0137(13) 0.0169(14) 0.0236(15) 0.0033(12) 0.0025(12) 0.0005(11) N4 0.0311(14) 0.0183(14) 0.0298(15) -0.0039(11) 0.0076(12) -0.0008(11) C3 0.0149(13) 0.0165(14) 0.0184(15) 0.0022(11) 0.0011(12) 0.0024(11) N3 0.0271(14) 0.0274(15) 0.0227(14) -0.0002(11) 0.0067(12) 0.0003(11) C5 0.0160(14) 0.0220(15) 0.0248(17) 0.0011(13) -0.0011(13) 0.0009(12) N5 0.0294(14) 0.0369(16) 0.0311(16) 0.0063(13) -0.0079(13) -0.0003(12) C6 0.0177(14) 0.0165(14) 0.0170(14) -0.0024(11) 0.0016(12) 0.0046(12) N6 0.0192(12) 0.0203(14) 0.0256(14) -0.0007(10) 0.0044(11) 0.0023(11) C11 0.0145(13) 0.0199(15) 0.0125(14) 0.0040(11) -0.0001(11) 0.0017(11) C12 0.0138(12) 0.0172(14) 0.0152(14) 0.0013(11) -0.0012(11) -0.0021(11) F12 0.0161(8) 0.0191(8) 0.0311(10) -0.0054(7) 0.0011(7) -0.0010(7) C14 0.0149(13) 0.0217(15) 0.0171(15) 0.0018(12) 0.0018(11) 0.0015(12) C13 0.0192(14) 0.0157(14) 0.0190(15) -0.0014(11) 0.0049(12) 0.0030(11) F13 0.0209(8) 0.0195(9) 0.0357(11) -0.0077(7) 0.0057(8) 0.0030(7) C15 0.0168(14) 0.0222(15) 0.0161(15) -0.0036(12) -0.0007(12) -0.0021(12) F15 0.0158(8) 0.0295(10) 0.0295(10) -0.0127(8) 0.0005(7) -0.0050(7) C16 0.0202(14) 0.0159(14) 0.0160(14) -0.0034(11) 0.0023(12) 0.0014(11) F16 0.0189(8) 0.0199(9) 0.0318(10) -0.0112(7) 0.0021(7) 0.0009(7) C17 0.0143(13) 0.0249(16) 0.0152(14) -0.0026(11) 0.0002(11) 0.0002(11) C19 0.0200(14) 0.0196(15) 0.0231(16) 0.0048(12) -0.0008(12) 0.0041(12) F19 0.0212(8) 0.0210(9) 0.0501(11) 0.0168(9) 0.0018(8) 0.0011(8) C18 0.0151(13) 0.0256(16) 0.0235(16) 0.0043(12) 0.0050(12) -0.0030(12) F18 0.0186(9) 0.0354(11) 0.0419(11) 0.0170(9) 0.0059(8) -0.0022(8) C20 0.0140(13) 0.0165(14) 0.0163(14) -0.0031(11) -0.0001(11) 0.0005(11) C21 0.0156(12) 0.0192(14) 0.0137(13) -0.0013(11) 0.0041(11) -0.0012(12) F21 0.0167(8) 0.0219(9) 0.0227(9) 0.0052(7) 0.0037(7) -0.0019(7) C22 0.0193(14) 0.0166(14) 0.0124(14) 0.0005(10) -0.0023(12) 0.0027(11) F22 0.0209(8) 0.0196(9) 0.0269(9) 0.0061(7) 0.0002(7) 0.0042(7) C30 0.0374(19) 0.036(2) 0.047(2) -0.0046(17) -0.0042(18) 0.0036(16) C31 0.0329(18) 0.059(3) 0.044(2) -0.0047(19) -0.0029(17) 0.0048(18) C32 0.049(2) 0.061(3) 0.059(3) 0.010(2) 0.006(2) 0.023(2) C33 0.033(2) 0.034(2) 0.072(3) 0.006(2) 0.005(2) 0.0100(17) C40 0.0215(15) 0.0344(19) 0.0333(19) 0.0068(15) 0.0022(14) -0.0020(14) C41 0.0242(16) 0.049(2) 0.036(2) 0.0029(17) 0.0059(15) 0.0062(16) C42 0.0317(18) 0.058(3) 0.0266(18) -0.0065(16) 0.0046(15) 0.0019(17) C43 0.0277(17) 0.058(3) 0.0323(19) -0.0200(17) -0.0003(15) 0.0018(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' H H 0.0000 0.0000 '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' 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' 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 O2 K1 O1 88.60(7) . . O2 K1 N4 100.68(7) . . O1 K1 N4 111.35(7) . . O2 K1 N6 123.21(8) . 4_557 O1 K1 N6 144.86(7) . 4_557 N4 K1 N6 79.57(7) . 4_557 O2 K1 N2 89.38(7) . 2_667 O1 K1 N2 83.02(7) . 2_667 N4 K1 N2 162.43(8) . 2_667 N6 K1 N2 82.87(7) 4_557 2_667 O2 K1 N1 160.23(8) . 3_455 O1 K1 N1 71.64(6) . 3_455 N4 K1 N1 86.45(7) . 3_455 N6 K1 N1 76.04(7) 4_557 3_455 N2 K1 N1 88.80(7) 2_667 3_455 O2 K1 C6 132.55(7) . 4_557 O1 K1 C6 129.52(7) . 4_557 N4 K1 C6 90.90(7) . 4_557 N6 K1 C6 16.16(6) 4_557 4_557 N2 K1 C6 71.79(7) 2_667 4_557 N1 K1 C6 64.99(7) 3_455 4_557 O2 K1 K2 117.24(6) . 4_556 O1 K1 K2 47.71(4) . 4_556 N4 K1 K2 132.88(6) . 4_556 N6 K1 K2 99.77(5) 4_557 4_556 N2 K1 K2 50.09(5) 2_667 4_556 N1 K1 K2 48.97(5) 3_455 4_556 C6 K1 K2 83.62(5) 4_557 4_556 O2 K1 K2 119.76(6) . 1_556 O1 K1 K2 140.58(5) . 1_556 N4 K1 K2 41.57(6) . 1_556 N6 K1 K2 38.01(5) 4_557 1_556 N2 K1 K2 120.86(5) 2_667 1_556 N1 K1 K2 77.63(5) 3_455 1_556 C6 K1 K2 50.16(5) 4_557 1_556 K2 K1 K2 122.058(17) 4_556 1_556 C1 N1 K1 132.5(2) . 3_545 C1 N1 K2 142.2(2) . 2_656 K1 N1 K2 83.46(6) 3_545 2_656 C40 O1 C43 108.7(2) . . C40 O1 K1 115.08(17) . . C43 O1 K1 113.1(2) . . C40 O1 K2 118.15(17) . 4_556 C43 O1 K2 113.06(17) . 4_556 K1 O1 K2 87.59(6) . 4_556 N1 C1 B1 175.5(3) . . C3 B1 C1 107.7(2) . . C3 B1 C2 108.2(2) . . C1 B1 C2 106.7(2) . . C3 B1 C11 110.3(2) . . C1 B1 C11 115.1(2) . . C2 B1 C11 108.6(2) . . C30 O2 C33 109.5(3) . . C30 O2 K1 118.61(19) . . C33 O2 K1 118.4(2) . . N5 K2 N6 88.59(8) . 4_556 N5 K2 O1 92.16(7) . 4_546 N6 K2 O1 149.39(7) 4_556 4_546 N5 K2 N3 76.19(8) . 3_455 N6 K2 N3 74.55(7) 4_556 3_455 O1 K2 N3 75.94(7) 4_546 3_455 N5 K2 N1 75.93(8) . 2_656 N6 K2 N1 140.31(7) 4_556 2_656 O1 K2 N1 68.80(6) 4_546 2_656 N3 K2 N1 133.55(7) 3_455 2_656 N5 K2 N2 159.75(8) . 3_454 N6 K2 N2 109.29(7) 4_556 3_454 O1 K2 N2 77.37(6) 4_546 3_454 N3 K2 N2 116.93(7) 3_455 3_454 N1 K2 N2 84.09(7) 2_656 3_454 N5 K2 N4 103.32(8) . 1_554 N6 K2 N4 74.15(7) 4_556 1_554 O1 K2 N4 134.88(7) 4_546 1_554 N3 K2 N4 148.69(7) 3_455 1_554 N1 K2 N4 74.30(7) 2_656 1_554 N2 K2 N4 73.81(7) 3_454 1_554 N5 K2 F21 134.43(7) . 4_556 N6 K2 F21 64.76(6) 4_556 4_556 O1 K2 F21 94.05(5) 4_546 4_556 N3 K2 F21 61.84(6) 3_455 4_556 N1 K2 F21 147.17(6) 2_656 4_556 N2 K2 F21 64.45(5) 3_454 4_556 N4 K2 F21 103.68(6) 1_554 4_556 N5 K2 C6 96.83(8) . 4_556 N6 K2 C6 17.09(6) 4_556 4_556 O1 K2 C6 133.59(7) 4_546 4_556 N3 K2 C6 62.48(7) 3_455 4_556 N1 K2 C6 157.30(7) 2_656 4_556 N2 K2 C6 102.95(6) 3_454 4_556 N4 K2 C6 86.83(7) 1_554 4_556 F21 K2 C6 49.26(5) 4_556 4_556 N5 K2 K1 115.11(6) . 4_546 N6 K2 K1 154.68(5) 4_556 4_546 O1 K2 K1 44.70(4) 4_546 4_546 N3 K2 K1 118.04(5) 3_455 4_546 N1 K2 K1 47.57(5) 2_656 4_546 N2 K2 K1 45.90(5) 3_454 4_546 N4 K2 K1 90.93(5) 1_554 4_546 F21 K2 K1 100.42(3) 4_556 4_546 C6 K2 K1 147.57(5) 4_556 4_546 N5 K2 K1 98.07(6) . 1_554 N6 K2 K1 37.04(5) 4_556 1_554 O1 K2 K1 168.49(5) 4_546 1_554 N3 K2 K1 111.58(5) 3_455 1_554 N1 K2 K1 108.54(5) 2_656 1_554 N2 K2 K1 91.28(5) 3_454 1_554 N4 K2 K1 37.12(5) 1_554 1_554 F21 K2 K1 82.57(3) 4_556 1_554 C6 K2 K1 50.47(5) 4_556 1_554 K1 K2 K1 124.947(17) 4_546 1_554 C2 N2 K1 161.8(2) . 2_647 C2 N2 K2 114.07(19) . 3_546 K1 N2 K2 84.01(6) 2_647 3_546 N2 C2 B1 178.5(3) . . C6 B2 C4 107.9(2) . . C6 B2 C5 105.7(2) . . C4 B2 C5 108.3(2) . . C6 B2 C20 115.0(2) . . C4 B2 C20 109.6(2) . . C5 B2 C20 110.1(2) . . N4 C4 B2 179.1(3) . . C4 N4 K1 134.7(2) . . C4 N4 K2 121.4(2) . 1_556 K1 N4 K2 101.31(8) . 1_556 N3 C3 B1 179.5(3) . . C3 N3 K2 154.3(2) . 3_545 N5 C5 B2 178.2(3) . . C5 N5 K2 157.0(2) . . N6 C6 B2 175.9(3) . . N6 C6 K2 47.44(16) . 4_546 B2 C6 K2 136.35(17) . 4_546 N6 C6 K1 43.03(16) . 4_547 B2 C6 K1 135.59(17) . 4_547 K2 C6 K1 79.38(6) 4_546 4_547 C6 N6 K1 120.8(2) . 4_547 C6 N6 K2 115.47(19) . 4_546 K1 N6 K2 104.95(8) 4_547 4_546 C12 C11 C16 114.4(2) . . C12 C11 B1 126.2(2) . . C16 C11 B1 119.4(2) . . F12 C12 C11 120.6(2) . . F12 C12 C13 116.3(2) . . C11 C12 C13 123.1(2) . . C13 C14 C15 116.1(2) . . C13 C14 C17 121.6(3) . . C15 C14 C17 122.2(2) . . F13 C13 C12 118.6(2) . . F13 C13 C14 119.6(2) . . C12 C13 C14 121.8(2) . . F15 C15 C16 119.2(2) . . F15 C15 C14 119.8(2) . . C16 C15 C14 121.1(2) . . F16 C16 C15 117.5(2) . . F16 C16 C11 119.0(2) . . C15 C16 C11 123.5(2) . . C22 C17 C18 116.0(2) . . C22 C17 C14 123.6(3) . . C18 C17 C14 120.4(3) . . F19 C19 C18 116.9(3) . . F19 C19 C20 120.1(2) . . C18 C19 C20 123.0(3) . . F18 C18 C19 118.6(3) . . F18 C18 C17 119.8(2) . . C19 C18 C17 121.6(3) . . C19 C20 C21 114.8(2) . . C19 C20 B2 119.9(2) . . C21 C20 B2 125.4(2) . . F21 C21 C22 117.1(2) . . F21 C21 C20 120.0(2) . . C22 C21 C20 122.8(2) . . C21 F21 K2 138.53(14) . 4_546 F22 C22 C21 118.5(2) . . F22 C22 C17 119.7(2) . . C21 C22 C17 121.7(2) . . O2 C30 C31 107.2(3) . . O2 C30 H30A 110.3 . . C31 C30 H30A 110.3 . . O2 C30 H30B 110.3 . . C31 C30 H30B 110.3 . . H30A C30 H30B 108.5 . . C30 C31 C32 101.8(3) . . C30 C31 H31A 111.4 . . C32 C31 H31A 111.4 . . C30 C31 H31B 111.4 . . C32 C31 H31B 111.4 . . H31A C31 H31B 109.3 . . C33 C32 C31 102.3(3) . . C33 C32 H32A 111.3 . . C31 C32 H32A 111.3 . . C33 C32 H32B 111.3 . . C31 C32 H32B 111.3 . . H32A C32 H32B 109.2 . . O2 C33 C32 105.8(3) . . O2 C33 H33A 110.6 . . C32 C33 H33A 110.6 . . O2 C33 H33B 110.6 . . C32 C33 H33B 110.6 . . H33A C33 H33B 108.7 . . O1 C40 C41 105.4(3) . . O1 C40 H40A 110.7 . . C41 C40 H40A 110.7 . . O1 C40 H40B 110.7 . . C41 C40 H40B 110.7 . . H40A C40 H40B 108.8 . . C40 C41 C42 101.8(3) . . C40 C41 H41A 111.4 . . C42 C41 H41A 111.4 . . C40 C41 H41B 111.4 . . C42 C41 H41B 111.4 . . H41A C41 H41B 109.3 . . C43 C42 C41 102.8(3) . . C43 C42 H42A 111.2 . . C41 C42 H42A 111.2 . . C43 C42 H42B 111.2 . . C41 C42 H42B 111.2 . . H42A C42 H42B 109.1 . . O1 C43 C42 107.0(3) . . O1 C43 H43A 110.3 . . C42 C43 H43A 110.3 . . O1 C43 H43B 110.3 . . C42 C43 H43B 110.3 . . H43A C43 H43B 108.6 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 K1 O2 2.684(2) . K1 O1 2.724(2) . K1 N4 2.754(3) . K1 N6 2.791(3) 4_557 K1 N2 2.793(2) 2_667 K1 N1 2.874(2) 3_455 K1 C6 3.512(3) 4_557 K1 K2 3.8685(9) 4_556 K1 K2 4.4756(9) 1_556 N1 C1 1.143(3) . N1 K1 2.874(2) 3_545 N1 K2 2.938(2) 2_656 O1 C40 1.448(3) . O1 C43 1.449(4) . O1 K2 2.864(2) 4_556 C1 B1 1.601(4) . B1 C3 1.591(4) . B1 C2 1.612(4) . B1 C11 1.625(4) . O2 C30 1.432(4) . O2 C33 1.435(4) . K2 N5 2.751(3) . K2 N6 2.852(2) 4_556 K2 O1 2.864(2) 4_546 K2 N3 2.867(3) 3_455 K2 N1 2.938(2) 2_656 K2 N2 2.984(2) 3_454 K2 N4 3.029(3) 1_554 K2 F21 3.1445(16) 4_556 K2 C6 3.496(3) 4_556 K2 K1 3.8684(9) 4_546 K2 K1 4.4756(9) 1_554 N2 C2 1.136(3) . N2 K1 2.793(2) 2_647 N2 K2 2.984(2) 3_546 B2 C6 1.595(4) . B2 C4 1.599(4) . B2 C5 1.604(4) . B2 C20 1.627(4) . C4 N4 1.142(4) . N4 K2 3.029(3) 1_556 C3 N3 1.142(4) . N3 K2 2.867(3) 3_545 C5 N5 1.138(4) . C6 N6 1.138(3) . C6 K2 3.496(3) 4_546 C6 K1 3.512(3) 4_547 N6 K1 2.790(3) 4_547 N6 K2 2.853(2) 4_546 C11 C12 1.380(4) . C11 C16 1.395(4) . C12 F12 1.350(3) . C12 C13 1.386(4) . C14 C13 1.387(4) . C14 C15 1.389(4) . C14 C17 1.481(4) . C13 F13 1.341(3) . C15 F15 1.343(3) . C15 C16 1.383(4) . C16 F16 1.349(3) . C17 C22 1.386(4) . C17 C18 1.389(4) . C19 F19 1.349(3) . C19 C18 1.378(4) . C19 C20 1.384(4) . C18 F18 1.342(3) . C20 C21 1.391(4) . C21 F21 1.351(3) . C21 C22 1.380(4) . F21 K2 3.1444(16) 4_546 C22 F22 1.346(3) . C30 C31 1.502(5) . C30 H30A 0.9900 . C30 H30B 0.9900 . C31 C32 1.529(6) . C31 H31A 0.9900 . C31 H31B 0.9900 . C32 C33 1.512(6) . C32 H32A 0.9900 . C32 H32B 0.9900 . C33 H33A 0.9900 . C33 H33B 0.9900 . C40 C41 1.517(5) . C40 H40A 0.9900 . C40 H40B 0.9900 . C41 C42 1.519(5) . C41 H41A 0.9900 . C41 H41B 0.9900 . C42 C43 1.497(5) . C42 H42A 0.9900 . C42 H42B 0.9900 . C43 H43A 0.9900 . C43 H43B 0.9900 .