#------------------------------------------------------------------------------ #$Date: 2017-05-23 04:59:31 +0300 (Tue, 23 May 2017) $ #$Revision: 196890 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/04/30/7043058.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_7043058 loop_ _publ_author_name 'Trommenschlager, Audrey' 'Chotard, Florian' 'Bertrand, Beno\^it' 'Amor, Souheila' 'Dondaine, Lucile' 'Picquet, Michel' 'Richard, Philippe' 'Bettaeib, Ali' 'Le Gendre, Pierre' 'Paul, Catherine' 'Goze, Christine' 'Bodio, Ewen' _publ_section_title ; Gold(I)-BODIPY-imidazole bimetallic complexes as new potential anti-inflammatory and anticancer trackable agents ; _journal_name_full 'Dalton Trans.' _journal_paper_doi 10.1039/C7DT01377A _journal_year 2017 _chemical_formula_moiety '2.5(C21 H15 B F2 N6), 0.5(C H2 Cl2)' _chemical_formula_sum 'C53 H38.5 B2.5 Cl F5 N15' _chemical_formula_weight 1042.96 _space_group_crystal_system orthorhombic _space_group_IT_number 18 _space_group_name_Hall 'P 2 2ab' _space_group_name_H-M_alt 'P 21 21 2' _symmetry_space_group_name_Hall 'P 2 2ab' _symmetry_space_group_name_H-M 'P 21 21 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2017-03-15 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324) ; _audit_update_record ; 2017-03-15 deposited with the CCDC. 2017-05-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.0671(5) _cell_length_b 32.4681(14) _cell_length_c 12.0173(5) _cell_measurement_reflns_used 9730 _cell_measurement_temperature 150 _cell_measurement_theta_max 23.148 _cell_measurement_theta_min 2.39 _cell_volume 4708.3(3) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector 'CCD Plate' _diffrn_detector_area_resol_mean '512 x 512' _diffrn_detector_type APEX2 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans'' _diffrn_radiation_collimation '0.6 mm' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_unetI/netI 0.0357 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 144944 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.516 _diffrn_reflns_theta_min 3.025 _diffrn_source 'X-ray tube' _diffrn_source_target Mo _diffrn_source_type 'Siemens KFF Mo 2K-180' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.160 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6548 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0813 before and 0.0749 after correction. The Ratio of minimum to maximum transmission is 0.8782. The \l/2 correction factor is Not present.' _exptl_crystal_colour violet _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.471 _exptl_crystal_description plate _exptl_crystal_F_000 2144 _exptl_crystal_preparation ', Luminescent' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH2Cl2' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.075 _refine_diff_density_max 0.908 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details ; Flack x determined using 3442 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.01(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 730 _refine_ls_number_reflns 10767 _refine_ls_number_restraints 60 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0538 _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^)+(0.0666P)^2^+2.3893P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1300 _refine_ls_wR_factor_ref 0.1380 _reflns_Friedel_coverage 0.805 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.996 _reflns_number_gt 9045 _reflns_number_total 10767 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; aud100217_0ma_a.res created by SHELXL-2014/7 TITL aud100217_0ma_a.res in P2(1)2(1)2 REM Old TITL aud100217_0ma in P2(1)2(1)2 REM SHELXT solution in P2(1)2(1)2 REM R1 0.175, Rweak 0.038, Alpha 0.003, Orientation as input REM Flack x = -0.406 ( 0.175 ) from Parsons' quotients REM Formula found by SHELXT: C114 B5 F11 N24 CELL 0.71073 12.0671 32.4681 12.0173 90 90 90 ZERR 4 0.0005 0.0014 0.0005 0 0 0 LATT -1 SYMM -X,-Y,+Z SYMM 0.5-X,0.5+Y,-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H B Cl F N UNIT 212 154 10 4 20 60 RIGU N3B N3 C16B C18 N4 C17B C17 N4B C16 C18B L.S. 4 PLAN 10 SIZE 0.075 0.3 0.5 TEMP -123.15 BOND $H LIST 6 fmap 2 acta OMIT 1 1 0 OMIT 0 2 1 OMIT 1 2 0 OMIT 0 8 3 OMIT 1 3 3 OMIT -1 3 3 OMIT 0 1 1 OMIT 2 2 0 OMIT 7 12 0 OMIT 1 1 1 OMIT -1 1 1 OMIT 0 5 1 OMIT 1 0 5 OMIT -1 2 1 OMIT 9 0 7 OMIT 1 2 1 OMIT 0 4 1 OMIT 0 6 0 OMIT 3 5 0 OMIT 4 0 2 OMIT 0 0 1 OMIT 3 10 0 OMIT 0 3 2 OMIT 10 2 0 OMIT 0 8 9 OMIT 2 6 0 OMIT 1 11 0 OMIT 8 20 0 OMIT 10 1 0 OMIT 0 13 2 OMIT 0 4 2 OMIT 0 2 8 OMIT 0 7 6 OMIT 3 0 5 OMIT 0 8 2 OMIT 2 0 2 OMIT -3 1 1 OMIT 3 1 1 OMIT -2 2 1 OMIT 3 9 0 OMIT 2 2 1 OMIT 1 4 7 OMIT -5 10 1 OMIT -1 4 7 OMIT 5 9 0 OMIT 0 9 2 OMIT 5 10 1 OMIT -10 6 4 OMIT 2 1 0 REM REM REM WGHT 0.066600 2.389300 FVAR 0.07942 0.55214 B1 3 0.269574 0.392388 0.460560 11.00000 0.02723 0.02992 = 0.02420 0.00379 0.00291 -0.00127 C1 1 0.320197 0.400856 0.672277 11.00000 0.03671 0.03073 = 0.02336 0.00214 0.00726 -0.00838 C2 1 0.412949 0.394960 0.740635 11.00000 0.03838 0.04243 = 0.01939 -0.00176 0.00329 -0.00916 AFIX 43 H2 2 0.415024 0.397119 0.819444 11.00000 -1.20000 AFIX 0 C3 1 0.500115 0.385482 0.672094 11.00000 0.03662 0.03691 = 0.02417 -0.00171 -0.00272 -0.00438 AFIX 43 H3 2 0.574297 0.380377 0.694687 11.00000 -1.20000 AFIX 0 C4 1 0.459717 0.384680 0.561895 11.00000 0.02805 0.02595 = 0.02227 -0.00154 0.00215 -0.00204 C5 1 0.516684 0.381005 0.461042 11.00000 0.02964 0.02009 = 0.02421 -0.00102 -0.00093 -0.00172 C6 1 0.459589 0.384719 0.359450 11.00000 0.02582 0.02546 = 0.02231 -0.00111 0.00090 -0.00213 C7 1 0.499075 0.384736 0.249200 11.00000 0.03012 0.02846 = 0.02455 -0.00344 0.00243 0.00446 AFIX 43 H7 2 0.573968 0.381325 0.226643 11.00000 -1.20000 AFIX 0 C8 1 0.409739 0.390575 0.180157 11.00000 0.03783 0.03214 = 0.02136 -0.00204 0.00426 0.00305 AFIX 43 H8 2 0.411396 0.392489 0.101291 11.00000 -1.20000 AFIX 0 C9 1 0.316341 0.393154 0.247715 11.00000 0.03326 0.02751 = 0.02282 -0.00044 -0.00199 0.00210 C10 1 0.638460 0.374126 0.461024 11.00000 0.03003 0.03446 = 0.02071 -0.00707 -0.00057 0.00140 C11 1 0.707245 0.398727 0.395892 11.00000 0.03311 0.03422 = 0.02760 -0.00646 0.00024 0.00051 AFIX 43 H11 2 0.676581 0.420069 0.351435 11.00000 -1.20000 AFIX 0 C12 1 0.820997 0.391911 0.396227 11.00000 0.03044 0.04752 = 0.03925 -0.00775 0.00447 -0.00433 AFIX 43 H12 2 0.867897 0.408767 0.351983 11.00000 -1.20000 AFIX 0 C13 1 0.866460 0.360925 0.460146 11.00000 0.02496 0.07104 = 0.03576 -0.01253 -0.00110 0.00623 AFIX 43 H13 2 0.944308 0.356567 0.460006 11.00000 -1.20000 AFIX 0 C14 1 0.798675 0.336275 0.524276 11.00000 0.03859 0.06405 = 0.03026 -0.00531 -0.00735 0.01390 AFIX 43 H14 2 0.830014 0.314869 0.568029 11.00000 -1.20000 AFIX 0 C15 1 0.684144 0.342639 0.525186 11.00000 0.03090 0.04692 = 0.02445 -0.00125 -0.00222 0.00574 AFIX 43 H15 2 0.637640 0.325592 0.569316 11.00000 -1.20000 AFIX 0 C19 1 0.113259 0.377377 0.239632 11.00000 0.03088 0.06825 = 0.03214 0.00646 -0.00151 -0.00400 AFIX 43 H19 2 0.108750 0.359491 0.302031 11.00000 -1.20000 AFIX 0 C20 1 0.071852 0.411747 0.094452 11.00000 0.03782 0.08152 = 0.04379 0.01621 -0.00735 0.01013 AFIX 43 H20 2 0.030278 0.422931 0.034505 11.00000 -1.20000 AFIX 0 C21 1 0.179963 0.420015 0.114171 11.00000 0.04612 0.06106 = 0.03560 0.01486 0.00094 0.00755 AFIX 43 H21 2 0.227473 0.437251 0.071687 11.00000 -1.20000 AFIX 0 F1 5 0.204471 0.356583 0.467896 11.00000 0.03319 0.04028 = 0.03087 0.00594 -0.00245 -0.01069 F2 5 0.200934 0.426193 0.453738 11.00000 0.03045 0.04051 = 0.03121 0.00402 0.00726 0.00975 N1 6 0.346477 0.394365 0.564080 11.00000 0.02693 0.02702 = 0.02350 0.00262 0.00305 -0.00198 N2 6 0.345161 0.390039 0.356820 11.00000 0.02613 0.02619 = 0.02040 -0.00011 -0.00118 0.00135 PART 1 AFIX 6 N3 6 0.208551 0.413586 0.701733 21.00000 0.03320 0.03635 = 0.01919 -0.00316 0.00824 -0.00249 C18 1 0.107582 0.402525 0.663614 21.00000 0.02788 0.05052 = 0.02594 -0.00157 0.00632 -0.01023 AFIX 43 H18 2 0.095880 0.383399 0.604953 21.00000 -1.20000 AFIX 5 C16 1 0.190600 0.441420 0.785523 21.00000 0.03780 0.06429 = 0.03794 -0.02350 0.01689 -0.01492 AFIX 43 H16 2 0.245364 0.454926 0.829042 21.00000 -1.20000 AFIX 5 C17 1 0.079690 0.445851 0.793989 21.00000 0.03085 0.07272 = 0.05261 -0.02318 0.02054 -0.00992 AFIX 43 H17 2 0.043101 0.463376 0.845539 21.00000 -1.20000 AFIX 5 N4 6 0.027641 0.421328 0.717216 21.00000 0.03533 0.06156 = 0.04128 -0.00784 0.01142 -0.00808 AFIX 0 PART 0 N5 6 0.206980 0.398005 0.209635 11.00000 0.03305 0.04543 = 0.02469 0.00219 -0.00281 0.00772 N6 6 0.030108 0.385010 0.172672 11.00000 0.03059 0.09847 = 0.03575 0.00526 -0.00651 -0.00163 PART 2 AFIX 6 N3B 6 0.224152 0.415268 0.718014 -21.00000 0.02283 0.04908 = 0.02170 -0.00041 -0.00314 -0.01552 C18B 1 0.217276 0.438199 0.811422 -21.00000 0.03381 0.05465 = 0.02066 -0.01027 0.00367 -0.01582 AFIX 43 H18B 2 0.278883 0.444921 0.857167 -21.00000 -1.20000 AFIX 5 C16B 1 0.118652 0.412495 0.676294 -21.00000 0.02898 0.10339 = 0.02459 -0.01618 0.00149 -0.01790 AFIX 43 H16B 2 0.096068 0.398312 0.610973 -21.00000 -1.20000 AFIX 5 C17B 1 0.053278 0.433974 0.746701 -21.00000 0.02255 0.09839 = 0.03428 -0.01404 0.00739 -0.01276 AFIX 43 H17B 2 -0.024489 0.437409 0.738618 -21.00000 -1.20000 AFIX 5 N4B 6 0.115564 0.450067 0.831430 -21.00000 0.02884 0.06924 = 0.03959 -0.00854 0.00119 -0.00863 AFIX 0 PART 0 B2 3 0.491247 0.300746 0.026396 11.00000 0.02668 0.03128 = 0.01529 -0.00275 0.00346 0.00015 C22 1 0.697860 0.314133 0.087931 11.00000 0.02231 0.02730 = 0.02754 -0.00053 0.00921 0.00324 C23 1 0.761502 0.311134 0.185060 11.00000 0.02361 0.03923 = 0.03389 0.00383 0.00283 0.00033 AFIX 43 H23 2 0.837058 0.318743 0.193458 11.00000 -1.20000 AFIX 0 C24 1 0.693799 0.295123 0.265521 11.00000 0.02230 0.03212 = 0.02803 0.00089 -0.00020 0.00251 AFIX 43 H24 2 0.714202 0.289400 0.340291 11.00000 -1.20000 AFIX 0 C25 1 0.588316 0.288605 0.217892 11.00000 0.02589 0.02530 = 0.01964 -0.00085 0.00190 0.00141 C26 1 0.489412 0.276941 0.267531 11.00000 0.02726 0.02443 = 0.01993 -0.00188 0.00286 0.00130 C27 1 0.390254 0.278263 0.207538 11.00000 0.02524 0.03223 = 0.02092 0.00127 0.00240 -0.00261 C28 1 0.280533 0.269695 0.241739 11.00000 0.02358 0.05119 = 0.02752 0.00518 0.00296 -0.00779 AFIX 43 H28 2 0.258301 0.259594 0.312494 11.00000 -1.20000 AFIX 0 C29 1 0.211942 0.278692 0.153607 11.00000 0.02439 0.05986 = 0.03012 0.00378 -0.00177 -0.00726 AFIX 43 H29 2 0.133472 0.276364 0.152547 11.00000 -1.20000 AFIX 0 C30 1 0.278865 0.291829 0.066358 11.00000 0.02818 0.03709 = 0.02349 -0.00136 -0.00080 -0.00279 C31 1 0.487103 0.265718 0.388180 11.00000 0.02391 0.02588 = 0.02115 0.00170 0.00169 -0.00263 C32 1 0.411445 0.285032 0.459641 11.00000 0.02771 0.02728 = 0.02498 -0.00032 0.00415 0.00071 AFIX 43 H32 2 0.361214 0.304860 0.430739 11.00000 -1.20000 AFIX 0 C33 1 0.409154 0.275513 0.571931 11.00000 0.03437 0.03692 = 0.02222 0.00003 0.00646 0.00161 AFIX 43 H33 2 0.357397 0.288660 0.619750 11.00000 -1.20000 AFIX 0 C34 1 0.482586 0.246767 0.614159 11.00000 0.04072 0.04054 = 0.02099 0.00694 0.00230 -0.00060 AFIX 43 H34 2 0.480994 0.240223 0.691192 11.00000 -1.20000 AFIX 0 C35 1 0.558345 0.227457 0.545217 11.00000 0.03343 0.03429 = 0.03034 0.00745 -0.00048 0.00402 AFIX 43 H35 2 0.608618 0.207827 0.575017 11.00000 -1.20000 AFIX 0 C36 1 0.560886 0.236874 0.431349 11.00000 0.02567 0.03057 = 0.02476 0.00085 0.00153 0.00241 AFIX 43 H36 2 0.612748 0.223626 0.383852 11.00000 -1.20000 AFIX 0 C37 1 0.700201 0.325337 -0.119555 11.00000 0.05982 0.05672 = 0.02913 -0.00445 0.01827 -0.01524 AFIX 43 H37 2 0.636009 0.310131 -0.139720 11.00000 -1.20000 AFIX 0 PART 1 C38 1 0.848916 0.363190 -0.124708 11.00000 0.03923 0.06205 = 0.06210 0.02634 0.02624 0.00787 AFIX 43 H38 2 0.908284 0.379387 -0.152646 11.00000 -1.20000 AFIX 0 PART 0 C39 1 0.832440 0.354081 -0.019354 11.00000 0.02719 0.05695 = 0.05249 0.01346 0.00504 -0.00603 AFIX 43 H39 2 0.877004 0.362709 0.041502 11.00000 -1.20000 AFIX 0 C40 1 0.284586 0.300004 -0.142789 11.00000 0.03577 0.04621 = 0.02318 -0.00766 -0.00387 0.00367 AFIX 43 H40 2 0.357586 0.290305 -0.156548 11.00000 -1.20000 AFIX 0 C41 1 0.121519 0.322570 -0.166381 11.00000 0.03754 0.05908 = 0.03285 -0.00045 -0.00866 0.01306 AFIX 43 H41 2 0.056697 0.332638 -0.202056 11.00000 -1.20000 AFIX 0 C42 1 0.131839 0.317419 -0.056146 11.00000 0.03443 0.06681 = 0.03333 -0.00101 -0.00086 0.01224 AFIX 43 H42 2 0.076743 0.322301 -0.001241 11.00000 -1.20000 AFIX 0 F3 5 0.503747 0.269647 -0.053292 11.00000 0.03523 0.03856 = 0.02364 -0.00998 0.00242 0.00268 F4 5 0.481053 0.338549 -0.026505 11.00000 0.03942 0.03397 = 0.01873 0.00323 0.00370 0.00128 N7 6 0.593269 0.300900 0.105912 11.00000 0.02229 0.02896 = 0.01943 0.00078 0.00489 0.00056 N8 6 0.386487 0.291680 0.096835 11.00000 0.02606 0.03180 = 0.01810 -0.00068 -0.00095 -0.00110 N9 6 0.737702 0.329451 -0.012901 11.00000 0.02521 0.03697 = 0.03380 0.00870 0.01141 0.00304 N10 6 0.763368 0.344869 -0.190612 11.00000 0.09118 0.06266 = 0.04854 0.00706 0.03846 -0.00522 N11 6 0.238838 0.303565 -0.038413 11.00000 0.02694 0.04058 = 0.02502 -0.00337 -0.00282 0.00120 N12 6 0.216079 0.311488 -0.220523 11.00000 0.03772 0.04960 = 0.02752 -0.00378 -0.00568 0.00024 B3 3 0.500000 0.500000 0.877896 10.50000 0.02461 0.03604 = 0.02806 0.00000 0.00000 0.00308 C43 1 0.681251 0.460499 0.829574 11.00000 0.02867 0.03956 = 0.03657 -0.00143 -0.00271 0.00379 C44 1 0.743341 0.448809 0.736346 11.00000 0.03412 0.06118 = 0.04333 -0.00956 -0.00035 0.01329 AFIX 43 H44 2 0.812567 0.434875 0.736205 11.00000 -1.20000 AFIX 0 C45 1 0.684156 0.461511 0.645480 11.00000 0.03678 0.04498 = 0.03366 -0.01057 0.00159 0.00396 AFIX 43 H45 2 0.704533 0.457420 0.569926 11.00000 -1.20000 AFIX 0 C46 1 0.587590 0.481744 0.683223 11.00000 0.03210 0.03032 = 0.03047 -0.00380 0.00017 -0.00402 C47 1 0.500000 0.500000 0.624896 10.50000 0.03472 0.02823 = 0.02553 0.00000 0.00000 -0.00401 C48 1 0.500000 0.500000 0.501542 10.50000 0.04267 0.02272 = 0.02986 0.00000 0.00000 -0.00358 C49 1 0.404087 0.489989 0.442381 11.00000 0.05169 0.02521 = 0.03834 0.00232 -0.00641 -0.00135 AFIX 43 H49 2 0.338064 0.482982 0.481054 11.00000 -1.20000 AFIX 0 C50 1 0.405559 0.490314 0.326923 11.00000 0.09038 0.02786 = 0.03901 -0.00336 -0.01994 0.00355 AFIX 43 H50 2 0.339770 0.483687 0.287368 11.00000 -1.20000 AFIX 0 C51 1 0.500000 0.500000 0.268343 10.50000 0.11304 0.03415 = 0.02941 0.00000 0.00000 0.00678 AFIX 43 H51 2 0.500000 0.500000 0.189290 10.50000 -1.20000 AFIX 0 C52 1 0.655041 0.430907 1.017938 11.00000 0.03378 0.08988 = 0.06185 0.03332 0.00184 0.00412 AFIX 43 H52 2 0.587791 0.416796 1.002579 11.00000 -1.20000 AFIX 0 C53 1 0.798725 0.454095 1.099800 11.00000 0.06148 0.06879 = 0.03718 0.00059 -0.01433 0.00861 AFIX 43 H53 2 0.851649 0.459889 1.156192 11.00000 -1.20000 AFIX 0 C54 1 0.804732 0.468345 0.993433 11.00000 0.04359 0.05346 = 0.04525 0.00314 -0.00697 -0.00523 AFIX 43 H54 2 0.862037 0.484554 0.961489 11.00000 -1.20000 AFIX 0 F5 5 0.551450 0.529628 0.942954 11.00000 0.03525 0.05278 = 0.03747 -0.01537 -0.00785 0.00652 N13 6 0.588099 0.480518 0.800194 11.00000 0.02552 0.03246 = 0.02737 -0.00209 0.00061 -0.00100 N14 6 0.710236 0.454288 0.942099 11.00000 0.02704 0.04852 = 0.03284 0.00221 0.00101 0.00847 N15 6 0.705350 0.430071 1.114805 11.00000 0.03629 0.10416 = 0.04830 0.02750 0.00637 0.01498 PART -3 AFIX 6 CL1 4 0.908569 0.486293 1.529739 10.50000 0.05938 0.07126 = 0.10238 0.03549 0.00955 -0.00070 CL2 4 1.036191 0.494861 1.323230 10.50000 0.14731 0.10552 = 0.06762 0.02806 0.02870 0.03916 C55 1 1.025722 0.507961 1.465010 10.50000 0.04559 0.07964 = 0.09902 -0.02433 0.01623 -0.02377 AFIX 23 H55A 2 1.093203 0.498448 1.504183 10.50000 -1.20000 H55B 2 1.022192 0.538314 1.472006 10.50000 -1.20000 AFIX 0 HKLF 4 REM aud100217_0ma_a.res in P2(1)2(1)2 REM R1 = 0.0538 for 9045 Fo > 4sig(Fo) and 0.0685 for all 10767 data REM 730 parameters refined using 60 restraints END WGHT 0.0666 2.3886 REM Highest difference peak 0.908, deepest hole -0.486, 1-sigma level 0.054 Q1 1 0.8957 0.3244 0.1746 11.00000 0.05 0.91 Q2 1 0.8562 0.4443 0.7110 11.00000 0.05 0.61 Q3 1 0.0758 0.3031 0.1685 11.00000 0.05 0.47 Q4 1 1.0008 0.5177 1.5480 11.00000 0.05 0.44 Q5 1 1.1026 0.5059 1.3652 11.00000 0.05 0.31 Q6 1 0.6574 0.4570 1.0545 11.00000 0.05 0.30 Q7 1 0.7270 0.4575 1.1474 11.00000 0.05 0.27 Q8 1 0.8320 0.3109 -0.0678 11.00000 0.05 0.27 Q9 1 0.0435 0.4157 0.1870 11.00000 0.05 0.24 Q10 1 0.8459 0.3204 -0.1757 11.00000 0.05 0.23 REM The information below was added by Olex2. REM REM R1 = 0.0538 for 9045 Fo > 4sig(Fo) and 0.0685 for all 145847 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.91, deepest hole -0.49 REM Mean Shift 0, Max Shift -0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0685 REM R1_gt = 0.0538 REM wR_ref = 0.1380 REM GOOF = 1.071 REM Shift_max = -0.001 REM Shift_mean = 0 REM Reflections_all = 145847 REM Reflections_gt = 9045 REM Parameters = n/a REM Hole = -0.49 REM Peak = 0.91 REM Flack = -0.01(4) ; _cod_data_source_file c7dt01377a3.cif _cod_data_source_block aud100217_0ma_a _cod_original_formula_sum 'C53 H38.50 B2.50 Cl F5 N15' _cod_database_code 7043058 _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_max 0.988 _shelx_estimated_absorpt_t_min 0.924 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Rigid body (RIGU) restrains N3B, N3, C16B, C18, N4, C17B, C17, N4B, C16, C18B with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 3. Others Sof(N3B)=Sof(C18B)=Sof(H18B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(N4B)= 1-FVAR(1) Sof(N3)=Sof(C18)=Sof(H18)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(N4)=FVAR(1) Fixed Sof: Cl1(0.5) Cl2(0.5) C55(0.5) H55A(0.5) H55B(0.5) 4.a Free rotating group: N3(C18,C16,C17,N4), N3B(C18B,C16B,C17B,N4B), Cl1(Cl2,C55) 4.b Secondary CH2 refined with riding coordinates: C55(H55A,H55B) 4.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C18(H18), C16(H16), C17(H17), C18B(H18B), C16B(H16B), C17B(H17B), C23(H23), C24(H24), C28(H28), C29(H29), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C44(H44), C45(H45), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54) ; _olex2_submission_special_instructions 'No special instructions were received' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.2696(3) 0.39239(13) 0.4606(3) 0.0271(8) Uani 1 1 d . . . . . C1 C 0.3202(3) 0.40086(11) 0.6723(3) 0.0303(8) Uani 1 1 d . . . . . C2 C 0.4129(3) 0.39496(13) 0.7406(3) 0.0334(8) Uani 1 1 d . . . . . H2 H 0.4150 0.3971 0.8194 0.040 Uiso 1 1 calc R . . . . C3 C 0.5001(3) 0.38548(12) 0.6721(3) 0.0326(8) Uani 1 1 d . . . . . H3 H 0.5743 0.3804 0.6947 0.039 Uiso 1 1 calc R . . . . C4 C 0.4597(3) 0.38468(11) 0.5619(3) 0.0254(7) Uani 1 1 d . . . . . C5 C 0.5167(3) 0.38101(10) 0.4610(3) 0.0246(7) Uani 1 1 d . . . . . C6 C 0.4596(3) 0.38472(11) 0.3595(3) 0.0245(7) Uani 1 1 d . . . . . C7 C 0.4991(3) 0.38474(11) 0.2492(3) 0.0277(7) Uani 1 1 d . . . . . H7 H 0.5740 0.3813 0.2266 0.033 Uiso 1 1 calc R . . . . C8 C 0.4097(3) 0.39057(11) 0.1802(3) 0.0304(8) Uani 1 1 d . . . . . H8 H 0.4114 0.3925 0.1013 0.037 Uiso 1 1 calc R . . . . C9 C 0.3163(3) 0.39315(11) 0.2477(3) 0.0279(7) Uani 1 1 d . . . . . C10 C 0.6385(3) 0.37413(11) 0.4610(3) 0.0284(7) Uani 1 1 d . . . . . C11 C 0.7072(3) 0.39873(12) 0.3959(3) 0.0316(8) Uani 1 1 d . . . . . H11 H 0.6766 0.4201 0.3514 0.038 Uiso 1 1 calc R . . . . C12 C 0.8210(3) 0.39191(14) 0.3962(4) 0.0391(9) Uani 1 1 d . . . . . H12 H 0.8679 0.4088 0.3520 0.047 Uiso 1 1 calc R . . . . C13 C 0.8665(3) 0.36092(16) 0.4601(4) 0.0439(11) Uani 1 1 d . . . . . H13 H 0.9443 0.3566 0.4600 0.053 Uiso 1 1 calc R . . . . C14 C 0.7987(4) 0.33627(15) 0.5243(3) 0.0443(10) Uani 1 1 d . . . . . H14 H 0.8300 0.3149 0.5680 0.053 Uiso 1 1 calc R . . . . C15 C 0.6841(3) 0.34264(13) 0.5252(3) 0.0341(8) Uani 1 1 d . . . . . H15 H 0.6376 0.3256 0.5693 0.041 Uiso 1 1 calc R . . . . C19 C 0.1133(3) 0.37738(16) 0.2396(4) 0.0438(10) Uani 1 1 d . . . . . H19 H 0.1088 0.3595 0.3020 0.053 Uiso 1 1 calc R . . . . C20 C 0.0719(4) 0.41175(18) 0.0945(4) 0.0544(13) Uani 1 1 d . . . . . H20 H 0.0303 0.4229 0.0345 0.065 Uiso 1 1 calc R . . . . C21 C 0.1800(4) 0.42002(16) 0.1142(4) 0.0476(11) Uani 1 1 d . . . . . H21 H 0.2275 0.4373 0.0717 0.057 Uiso 1 1 calc R . . . . F1 F 0.20447(18) 0.35658(7) 0.46790(18) 0.0348(5) Uani 1 1 d . . . . . F2 F 0.20093(18) 0.42619(7) 0.45374(18) 0.0341(5) Uani 1 1 d . . . . . N1 N 0.3465(2) 0.39437(9) 0.5641(2) 0.0258(6) Uani 1 1 d . . . . . N2 N 0.3452(2) 0.39004(9) 0.3568(2) 0.0242(6) Uani 1 1 d . . . . . N3 N 0.2086(8) 0.4136(5) 0.7017(13) 0.030(3) Uani 0.55(3) 1 d . U . A 1 C18 C 0.1076(9) 0.4025(4) 0.6636(10) 0.035(2) Uani 0.55(3) 1 d G U . A 1 H18 H 0.0959 0.3834 0.6050 0.042 Uiso 0.55(3) 1 calc R . . A 1 C16 C 0.1906(10) 0.4414(4) 0.7855(12) 0.047(3) Uani 0.55(3) 1 d G U . A 1 H16 H 0.2454 0.4549 0.8290 0.056 Uiso 0.55(3) 1 calc R . . A 1 C17 C 0.0797(11) 0.4459(3) 0.7940(12) 0.052(4) Uani 0.55(3) 1 d G U . A 1 H17 H 0.0431 0.4634 0.8455 0.062 Uiso 0.55(3) 1 calc R . . A 1 N4 N 0.0276(8) 0.4213(3) 0.7172(10) 0.046(3) Uani 0.55(3) 1 d G U . A 1 N5 N 0.2070(3) 0.39800(11) 0.2096(3) 0.0344(7) Uani 1 1 d . . . . . N6 N 0.0301(3) 0.38501(16) 0.1727(3) 0.0549(11) Uani 1 1 d . . . . . N3B N 0.2242(9) 0.4153(7) 0.7180(15) 0.031(3) Uani 0.45(3) 1 d . U . A 2 C18B C 0.2173(9) 0.4382(5) 0.8114(13) 0.036(3) Uani 0.45(3) 1 d G U . A 2 H18B H 0.2789 0.4449 0.8572 0.044 Uiso 0.45(3) 1 calc R . . A 2 C16B C 0.1187(11) 0.4125(7) 0.6763(12) 0.052(5) Uani 0.45(3) 1 d G U . A 2 H16B H 0.0961 0.3983 0.6110 0.063 Uiso 0.45(3) 1 calc R . . A 2 C17B C 0.0533(8) 0.4340(6) 0.7467(10) 0.052(4) Uani 0.45(3) 1 d G U . A 2 H17B H -0.0245 0.4374 0.7386 0.062 Uiso 0.45(3) 1 calc R . . A 2 N4B N 0.1156(11) 0.4501(4) 0.8314(11) 0.046(4) Uani 0.45(3) 1 d G U . A 2 B2 B 0.4912(3) 0.30075(12) 0.0264(3) 0.0244(8) Uani 1 1 d . . . . . C22 C 0.6979(3) 0.31413(11) 0.0879(3) 0.0257(7) Uani 1 1 d . . . . . C23 C 0.7615(3) 0.31113(12) 0.1851(3) 0.0322(8) Uani 1 1 d . . . . . H23 H 0.8371 0.3187 0.1935 0.039 Uiso 1 1 calc R . . . . C24 C 0.6938(3) 0.29512(11) 0.2655(3) 0.0275(7) Uani 1 1 d . . . . . H24 H 0.7142 0.2894 0.3403 0.033 Uiso 1 1 calc R . . . . C25 C 0.5883(3) 0.28860(10) 0.2179(3) 0.0236(7) Uani 1 1 d . . . . . C26 C 0.4894(3) 0.27694(10) 0.2675(3) 0.0239(7) Uani 1 1 d . . . . . C27 C 0.3903(3) 0.27826(11) 0.2075(3) 0.0261(7) Uani 1 1 d . . . . . C28 C 0.2805(3) 0.26970(13) 0.2417(3) 0.0341(9) Uani 1 1 d . . . . . H28 H 0.2583 0.2596 0.3125 0.041 Uiso 1 1 calc R . . . . C29 C 0.2119(3) 0.27869(14) 0.1536(3) 0.0381(9) Uani 1 1 d . . . . . H29 H 0.1335 0.2764 0.1525 0.046 Uiso 1 1 calc R . . . . C30 C 0.2789(3) 0.29183(12) 0.0664(3) 0.0296(8) Uani 1 1 d . . . . . C31 C 0.4871(3) 0.26572(10) 0.3882(3) 0.0236(7) Uani 1 1 d . . . . . C32 C 0.4114(3) 0.28503(11) 0.4596(3) 0.0267(7) Uani 1 1 d . . . . . H32 H 0.3612 0.3049 0.4307 0.032 Uiso 1 1 calc R . . . . C33 C 0.4092(3) 0.27551(12) 0.5719(3) 0.0312(8) Uani 1 1 d . . . . . H33 H 0.3574 0.2887 0.6197 0.037 Uiso 1 1 calc R . . . . C34 C 0.4826(3) 0.24677(12) 0.6142(3) 0.0341(8) Uani 1 1 d . . . . . H34 H 0.4810 0.2402 0.6912 0.041 Uiso 1 1 calc R . . . . C35 C 0.5583(3) 0.22746(12) 0.5452(3) 0.0327(8) Uani 1 1 d . . . . . H35 H 0.6086 0.2078 0.5750 0.039 Uiso 1 1 calc R . . . . C36 C 0.5609(3) 0.23687(11) 0.4313(3) 0.0270(7) Uani 1 1 d . . . . . H36 H 0.6127 0.2236 0.3839 0.032 Uiso 1 1 calc R . . . . C37 C 0.7002(4) 0.32534(15) -0.1196(4) 0.0486(11) Uani 1 1 d . . . . . H37 H 0.6360 0.3101 -0.1397 0.058 Uiso 1 1 calc R . . . . C38 C 0.8489(4) 0.36319(16) -0.1247(5) 0.0545(13) Uani 1 1 d . . . B 1 H38 H 0.9083 0.3794 -0.1526 0.065 Uiso 1 1 calc R . . B 1 C39 C 0.8324(3) 0.35408(15) -0.0194(4) 0.0455(11) Uani 1 1 d . . . . . H39 H 0.8770 0.3627 0.0415 0.055 Uiso 1 1 calc R . . B . C40 C 0.2846(3) 0.30000(13) -0.1428(3) 0.0351(9) Uani 1 1 d . . . . . H40 H 0.3576 0.2903 -0.1565 0.042 Uiso 1 1 calc R . . . . C41 C 0.1215(4) 0.32257(15) -0.1664(4) 0.0432(10) Uani 1 1 d . . . . . H41 H 0.0567 0.3326 -0.2021 0.052 Uiso 1 1 calc R . . . . C42 C 0.1318(4) 0.31742(16) -0.0561(4) 0.0449(11) Uani 1 1 d . . . . . H42 H 0.0767 0.3223 -0.0012 0.054 Uiso 1 1 calc R . . . . F3 F 0.50375(18) 0.26965(7) -0.05329(17) 0.0325(5) Uani 1 1 d . . . . . F4 F 0.48105(18) 0.33855(6) -0.02650(16) 0.0307(5) Uani 1 1 d . . . . . N7 N 0.5933(2) 0.30090(9) 0.1059(2) 0.0236(6) Uani 1 1 d . . . . . N8 N 0.3865(2) 0.29168(9) 0.0968(2) 0.0253(6) Uani 1 1 d . . . . . N9 N 0.7377(3) 0.32945(10) -0.0129(3) 0.0320(7) Uani 1 1 d . . . . . N10 N 0.7634(5) 0.34487(15) -0.1906(4) 0.0675(14) Uani 1 1 d . . . . . N11 N 0.2388(3) 0.30356(10) -0.0384(3) 0.0308(7) Uani 1 1 d . . . . . N12 N 0.2161(3) 0.31149(11) -0.2205(3) 0.0383(8) Uani 1 1 d . . . . . B3 B 0.5000 0.5000 0.8779(5) 0.0296(12) Uani 1 2 d S T P . . C43 C 0.6813(3) 0.46050(13) 0.8296(3) 0.0349(9) Uani 1 1 d . . . . . C44 C 0.7433(4) 0.44881(16) 0.7363(4) 0.0462(11) Uani 1 1 d . . . . . H44 H 0.8126 0.4349 0.7362 0.055 Uiso 1 1 calc R . . . . C45 C 0.6842(3) 0.46151(13) 0.6455(3) 0.0385(9) Uani 1 1 d . . . . . H45 H 0.7045 0.4574 0.5699 0.046 Uiso 1 1 calc R . . . . C46 C 0.5876(3) 0.48174(12) 0.6832(3) 0.0310(8) Uani 1 1 d . . . . . C47 C 0.5000 0.5000 0.6249(4) 0.0295(11) Uani 1 2 d S T P . . C48 C 0.5000 0.5000 0.5015(4) 0.0317(11) Uani 1 2 d S T P . . C49 C 0.4041(4) 0.48999(11) 0.4424(4) 0.0384(9) Uani 1 1 d . . . . . H49 H 0.3381 0.4830 0.4811 0.046 Uiso 1 1 calc R . . . . C50 C 0.4056(5) 0.49031(13) 0.3269(4) 0.0524(13) Uani 1 1 d . . . . . H50 H 0.3398 0.4837 0.2874 0.063 Uiso 1 1 calc R . . . . C51 C 0.5000 0.5000 0.2683(5) 0.059(2) Uani 1 2 d S T P . . H51 H 0.5000 0.5000 0.1893 0.071 Uiso 1 2 calc RS T P . . C52 C 0.6550(4) 0.4309(2) 1.0179(5) 0.0618(15) Uani 1 1 d . . . . . H52 H 0.5878 0.4168 1.0026 0.074 Uiso 1 1 calc R . . . . C53 C 0.7987(5) 0.45410(17) 1.0998(4) 0.0558(13) Uani 1 1 d . . . . . H53 H 0.8516 0.4599 1.1562 0.067 Uiso 1 1 calc R . . . . C54 C 0.8047(4) 0.46835(15) 0.9934(4) 0.0474(11) Uani 1 1 d . . . . . H54 H 0.8620 0.4846 0.9615 0.057 Uiso 1 1 calc R . . . . F5 F 0.55145(19) 0.52963(8) 0.9430(2) 0.0418(6) Uani 1 1 d . . . . . N13 N 0.5881(3) 0.48052(10) 0.8002(2) 0.0284(6) Uani 1 1 d . . . . . N14 N 0.7102(3) 0.45429(11) 0.9421(3) 0.0361(7) Uani 1 1 d . . . . . N15 N 0.7054(3) 0.43007(16) 1.1148(4) 0.0629(13) Uani 1 1 d . . . . . Cl1 Cl 0.9086(2) 0.48629(10) 1.5297(3) 0.0777(9) Uani 0.5 1 d . . . C -3 Cl2 Cl 1.0362(4) 0.49486(15) 1.3232(3) 0.1068(16) Uani 0.5 1 d G . . C -3 C55 C 1.0257(7) 0.5080(4) 1.4650(4) 0.075(4) Uani 0.5 1 d G . . C -3 H55A H 1.0932 0.4984 1.5042 0.090 Uiso 0.5 1 calc R . . C -3 H55B H 1.0222 0.5383 1.4720 0.090 Uiso 0.5 1 calc R . . C -3 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 B1 0.0272(19) 0.030(2) 0.0242(18) 0.0038(16) 0.0029(16) -0.0013(16) C1 0.037(2) 0.0307(19) 0.0234(17) 0.0021(14) 0.0073(15) -0.0084(16) C2 0.038(2) 0.042(2) 0.0194(16) -0.0018(15) 0.0033(15) -0.0092(17) C3 0.037(2) 0.037(2) 0.0242(17) -0.0017(15) -0.0027(16) -0.0044(17) C4 0.0281(17) 0.0259(17) 0.0223(16) -0.0015(13) 0.0022(14) -0.0020(14) C5 0.0296(18) 0.0201(15) 0.0242(16) -0.0010(13) -0.0009(15) -0.0017(13) C6 0.0258(17) 0.0255(17) 0.0223(16) -0.0011(13) 0.0009(13) -0.0021(14) C7 0.0301(18) 0.0285(18) 0.0245(16) -0.0034(14) 0.0024(15) 0.0045(15) C8 0.038(2) 0.0321(19) 0.0214(16) -0.0020(14) 0.0043(15) 0.0031(16) C9 0.0333(19) 0.0275(18) 0.0228(16) -0.0004(14) -0.0020(15) 0.0021(15) C10 0.0300(18) 0.0345(19) 0.0207(16) -0.0071(15) -0.0006(14) 0.0014(14) C11 0.033(2) 0.0342(19) 0.0276(18) -0.0065(15) 0.0002(16) 0.0005(16) C12 0.030(2) 0.048(2) 0.039(2) -0.0078(19) 0.0045(17) -0.0043(18) C13 0.0250(19) 0.071(3) 0.036(2) -0.013(2) -0.0011(17) 0.0062(19) C14 0.039(2) 0.064(3) 0.030(2) -0.0053(19) -0.0074(18) 0.014(2) C15 0.0309(19) 0.047(2) 0.0245(18) -0.0012(16) -0.0022(15) 0.0057(17) C19 0.031(2) 0.068(3) 0.032(2) 0.006(2) -0.0015(17) -0.004(2) C20 0.038(3) 0.082(4) 0.044(3) 0.016(2) -0.007(2) 0.010(2) C21 0.046(3) 0.061(3) 0.036(2) 0.015(2) 0.0009(19) 0.008(2) F1 0.0332(11) 0.0403(12) 0.0309(11) 0.0059(9) -0.0024(9) -0.0107(10) F2 0.0305(11) 0.0405(12) 0.0312(11) 0.0040(9) 0.0073(9) 0.0097(9) N1 0.0269(15) 0.0270(15) 0.0235(14) 0.0026(12) 0.0030(12) -0.0020(12) N2 0.0261(15) 0.0262(15) 0.0204(14) -0.0001(12) -0.0012(11) 0.0014(12) N3 0.033(5) 0.036(5) 0.019(5) -0.003(3) 0.008(4) -0.002(4) C18 0.028(4) 0.051(5) 0.026(5) -0.002(4) 0.006(3) -0.010(4) C16 0.038(6) 0.064(6) 0.038(7) -0.024(6) 0.017(4) -0.015(5) C17 0.031(6) 0.073(6) 0.053(8) -0.023(6) 0.021(5) -0.010(5) N4 0.035(5) 0.062(6) 0.041(5) -0.008(4) 0.011(4) -0.008(4) N5 0.0330(17) 0.0454(19) 0.0247(15) 0.0022(14) -0.0028(13) 0.0077(15) N6 0.0306(19) 0.098(3) 0.036(2) 0.005(2) -0.0065(16) -0.002(2) N3B 0.023(4) 0.049(7) 0.022(6) 0.000(5) -0.003(4) -0.016(4) C18B 0.034(5) 0.055(7) 0.021(5) -0.010(4) 0.004(4) -0.016(5) C16B 0.029(6) 0.103(13) 0.025(5) -0.016(7) 0.001(4) -0.018(6) C17B 0.023(5) 0.098(13) 0.034(8) -0.014(6) 0.007(5) -0.013(6) N4B 0.029(5) 0.069(7) 0.040(6) -0.009(5) 0.001(4) -0.009(5) B2 0.0267(19) 0.0313(19) 0.0153(16) -0.0028(14) 0.0035(15) 0.0002(16) C22 0.0223(16) 0.0273(17) 0.0275(17) -0.0005(13) 0.0092(14) 0.0032(14) C23 0.0236(18) 0.039(2) 0.034(2) 0.0038(16) 0.0028(15) 0.0003(15) C24 0.0223(17) 0.0321(18) 0.0280(17) 0.0009(14) -0.0002(14) 0.0025(14) C25 0.0259(17) 0.0253(16) 0.0196(15) -0.0008(13) 0.0019(13) 0.0014(13) C26 0.0273(17) 0.0244(16) 0.0199(15) -0.0019(12) 0.0029(13) 0.0013(13) C27 0.0252(18) 0.0322(18) 0.0209(16) 0.0013(14) 0.0024(14) -0.0026(14) C28 0.0236(18) 0.051(2) 0.0275(18) 0.0052(17) 0.0030(15) -0.0078(16) C29 0.0244(19) 0.060(3) 0.0301(19) 0.0038(18) -0.0018(16) -0.0073(18) C30 0.0282(19) 0.0371(19) 0.0235(17) -0.0014(15) -0.0008(14) -0.0028(15) C31 0.0239(17) 0.0259(16) 0.0211(16) 0.0017(13) 0.0017(13) -0.0026(13) C32 0.0277(17) 0.0273(17) 0.0250(16) -0.0003(14) 0.0042(15) 0.0007(14) C33 0.034(2) 0.037(2) 0.0222(17) 0.0000(14) 0.0065(15) 0.0016(16) C34 0.041(2) 0.041(2) 0.0210(17) 0.0069(15) 0.0023(16) -0.0006(17) C35 0.033(2) 0.0343(19) 0.0303(19) 0.0075(16) -0.0005(16) 0.0040(15) C36 0.0257(18) 0.0306(18) 0.0248(17) 0.0009(14) 0.0015(13) 0.0024(14) C37 0.060(3) 0.057(3) 0.029(2) -0.0045(19) 0.018(2) -0.015(2) C38 0.039(3) 0.062(3) 0.062(3) 0.026(3) 0.026(2) 0.008(2) C39 0.027(2) 0.057(3) 0.052(3) 0.013(2) 0.0050(18) -0.0060(19) C40 0.036(2) 0.046(2) 0.0232(17) -0.0077(16) -0.0039(16) 0.0037(18) C41 0.038(2) 0.059(3) 0.033(2) -0.0004(19) -0.0087(18) 0.013(2) C42 0.034(2) 0.067(3) 0.033(2) -0.001(2) -0.0009(18) 0.012(2) F3 0.0352(11) 0.0386(11) 0.0236(10) -0.0100(9) 0.0024(9) 0.0027(9) F4 0.0394(12) 0.0340(11) 0.0187(9) 0.0032(8) 0.0037(9) 0.0013(9) N7 0.0223(14) 0.0290(15) 0.0194(13) 0.0008(11) 0.0049(12) 0.0006(12) N8 0.0261(15) 0.0318(15) 0.0181(13) -0.0007(11) -0.0009(11) -0.0011(12) N9 0.0252(15) 0.0370(17) 0.0338(17) 0.0087(13) 0.0114(13) 0.0030(13) N10 0.091(4) 0.063(3) 0.049(2) 0.007(2) 0.038(3) -0.005(3) N11 0.0269(15) 0.0406(17) 0.0250(14) -0.0034(13) -0.0028(13) 0.0012(13) N12 0.0377(19) 0.050(2) 0.0275(17) -0.0038(15) -0.0057(14) 0.0002(16) B3 0.025(3) 0.036(3) 0.028(3) 0.000 0.000 0.003(2) C43 0.0287(19) 0.040(2) 0.037(2) -0.0014(17) -0.0027(16) 0.0038(16) C44 0.034(2) 0.061(3) 0.043(2) -0.010(2) -0.0004(19) 0.013(2) C45 0.037(2) 0.045(2) 0.034(2) -0.0106(18) 0.0016(17) 0.0040(18) C46 0.0321(19) 0.0303(18) 0.0305(19) -0.0038(15) 0.0002(16) -0.0040(16) C47 0.035(3) 0.028(2) 0.026(2) 0.000 0.000 -0.004(2) C48 0.043(3) 0.023(2) 0.030(3) 0.000 0.000 -0.004(2) C49 0.052(2) 0.0252(19) 0.038(2) 0.0023(15) -0.0064(19) -0.0013(17) C50 0.090(4) 0.028(2) 0.039(2) -0.0034(17) -0.020(3) 0.004(2) C51 0.113(7) 0.034(3) 0.029(3) 0.000 0.000 0.007(4) C52 0.034(2) 0.090(4) 0.062(3) 0.033(3) 0.002(2) 0.004(2) C53 0.061(3) 0.069(3) 0.037(2) 0.001(2) -0.014(2) 0.009(3) C54 0.044(2) 0.053(3) 0.045(2) 0.003(2) -0.007(2) -0.005(2) F5 0.0352(12) 0.0528(14) 0.0375(13) -0.0154(11) -0.0078(10) 0.0065(11) N13 0.0255(15) 0.0325(16) 0.0274(15) -0.0021(12) 0.0006(12) -0.0010(13) N14 0.0270(16) 0.0485(19) 0.0328(17) 0.0022(15) 0.0010(14) 0.0085(15) N15 0.036(2) 0.104(4) 0.048(2) 0.028(2) 0.0064(19) 0.015(2) Cl1 0.0594(16) 0.0713(18) 0.102(2) 0.0355(17) 0.0096(17) -0.0007(14) Cl2 0.147(5) 0.106(3) 0.0676(19) 0.028(2) 0.029(2) 0.039(3) C55 0.046(8) 0.080(10) 0.099(9) -0.024(7) 0.016(6) -0.024(5) 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' Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 '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 F1 B1 N1 108.5(3) . . F1 B1 N2 109.8(3) . . F2 B1 F1 109.1(3) . . F2 B1 N1 112.0(3) . . F2 B1 N2 110.2(3) . . N2 B1 N1 107.2(3) . . C2 C1 N3 129.5(7) . . N1 C1 C2 110.8(3) . . N1 C1 N3 119.7(7) . . N1 C1 N3B 129.7(9) . . N3B C1 C2 119.3(8) . . C1 C2 H2 126.5 . . C3 C2 C1 106.9(3) . . C3 C2 H2 126.5 . . C2 C3 H3 126.2 . . C2 C3 C4 107.6(4) . . C4 C3 H3 126.2 . . C5 C4 C3 130.2(3) . . C5 C4 N1 121.0(3) . . N1 C4 C3 108.4(3) . . C4 C5 C6 120.3(3) . . C4 C5 C10 119.9(3) . . C6 C5 C10 119.8(3) . . C5 C6 C7 130.6(3) . . N2 C6 C5 121.1(3) . . N2 C6 C7 108.3(3) . . C6 C7 H7 126.2 . . C8 C7 C6 107.6(3) . . C8 C7 H7 126.2 . . C7 C8 H8 126.5 . . C7 C8 C9 107.0(3) . . C9 C8 H8 126.5 . . C8 C9 N5 125.3(3) . . N2 C9 C8 110.5(3) . . N2 C9 N5 124.2(3) . . C11 C10 C5 120.2(3) . . C11 C10 C15 119.7(3) . . C15 C10 C5 120.1(3) . . C10 C11 H11 120.1 . . C12 C11 C10 119.7(4) . . C12 C11 H11 120.1 . . C11 C12 H12 119.7 . . C13 C12 C11 120.7(4) . . C13 C12 H12 119.7 . . C12 C13 H13 120.1 . . C12 C13 C14 119.9(4) . . C14 C13 H13 120.1 . . C13 C14 H14 119.8 . . C13 C14 C15 120.3(4) . . C15 C14 H14 119.8 . . C10 C15 C14 119.7(4) . . C10 C15 H15 120.2 . . C14 C15 H15 120.2 . . N5 C19 H19 123.8 . . N6 C19 H19 123.8 . . N6 C19 N5 112.3(4) . . C21 C20 H20 124.5 . . C21 C20 N6 111.0(4) . . N6 C20 H20 124.5 . . C20 C21 H21 127.2 . . C20 C21 N5 105.6(4) . . N5 C21 H21 127.2 . . C1 N1 B1 129.4(3) . . C1 N1 C4 106.3(3) . . C4 N1 B1 123.9(3) . . C6 N2 B1 124.9(3) . . C9 N2 B1 128.5(3) . . C9 N2 C6 106.5(3) . . C18 N3 C1 132.7(7) . . C18 N3 C16 106.4 . . C16 N3 C1 120.9(7) . . N3 C18 H18 124.0 . . N4 C18 N3 111.9 . . N4 C18 H18 124.0 . . N3 C16 H16 126.8 . . C17 C16 N3 106.4 . . C17 C16 H16 126.8 . . C16 C17 H17 125.0 . . C16 C17 N4 110.0 . . N4 C17 H17 125.0 . . C18 N4 C17 105.3 . . C19 N5 C9 129.6(3) . . C19 N5 C21 106.0(4) . . C21 N5 C9 123.1(4) . . C19 N6 C20 105.0(4) . . C1 N3B C16B 128.2(10) . . C18B N3B C1 125.2(10) . . C18B N3B C16B 106.5 . . N3B C18B H18B 124.1 . . N4B C18B N3B 111.9 . . N4B C18B H18B 124.1 . . N3B C16B H16B 126.9 . . C17B C16B N3B 106.2 . . C17B C16B H16B 126.9 . . C16B C17B H17B 125.0 . . C16B C17B N4B 110.0 . . N4B C17B H17B 125.0 . . C18B N4B C17B 105.4 . . F3 B2 N7 109.7(3) . . F3 B2 N8 108.9(3) . . F4 B2 F3 109.5(3) . . F4 B2 N7 110.4(3) . . F4 B2 N8 110.2(3) . . N8 B2 N7 108.1(3) . . N7 C22 C23 110.9(3) . . N7 C22 N9 125.1(3) . . N9 C22 C23 124.0(3) . . C22 C23 H23 126.6 . . C24 C23 C22 106.7(3) . . C24 C23 H23 126.6 . . C23 C24 H24 126.0 . . C23 C24 C25 108.0(3) . . C25 C24 H24 126.0 . . C26 C25 C24 130.0(3) . . C26 C25 N7 121.7(3) . . N7 C25 C24 107.9(3) . . C25 C26 C27 120.4(3) . . C25 C26 C31 120.0(3) . . C27 C26 C31 119.5(3) . . C26 C27 C28 130.2(3) . . C26 C27 N8 121.8(3) . . N8 C27 C28 107.9(3) . . C27 C28 H28 126.3 . . C29 C28 C27 107.3(3) . . C29 C28 H28 126.3 . . C28 C29 H29 126.4 . . C28 C29 C30 107.2(3) . . C30 C29 H29 126.4 . . C29 C30 N11 124.1(3) . . N8 C30 C29 110.7(3) . . N8 C30 N11 125.2(3) . . C32 C31 C26 119.8(3) . . C36 C31 C26 120.9(3) . . C36 C31 C32 119.3(3) . . C31 C32 H32 119.7 . . C33 C32 C31 120.7(3) . . C33 C32 H32 119.7 . . C32 C33 H33 120.2 . . C34 C33 C32 119.7(3) . . C34 C33 H33 120.2 . . C33 C34 H34 119.7 . . C33 C34 C35 120.6(3) . . C35 C34 H34 119.7 . . C34 C35 H35 120.0 . . C34 C35 C36 120.0(3) . . C36 C35 H35 120.0 . . C31 C36 C35 119.7(3) . . C31 C36 H36 120.1 . . C35 C36 H36 120.1 . . N9 C37 H37 124.1 . . N10 C37 H37 124.1 . . N10 C37 N9 111.8(5) . . C39 C38 H38 125.4 . . C39 C38 N10 109.3(4) . . N10 C38 H38 125.4 . . C38 C39 H39 126.1 . . C38 C39 N9 107.8(4) . . N9 C39 H39 126.1 . . N11 C40 H40 124.0 . . N12 C40 H40 124.0 . . N12 C40 N11 112.1(4) . . C42 C41 H41 124.4 . . C42 C41 N12 111.2(4) . . N12 C41 H41 124.4 . . C41 C42 H42 126.9 . . C41 C42 N11 106.2(4) . . N11 C42 H42 126.9 . . C22 N7 B2 129.9(3) . . C22 N7 C25 106.5(3) . . C25 N7 B2 123.6(3) . . C27 N8 B2 123.5(3) . . C30 N8 B2 129.5(3) . . C30 N8 C27 106.9(3) . . C22 N9 C39 122.3(4) . . C37 N9 C22 131.8(3) . . C37 N9 C39 106.0(3) . . C37 N10 C38 105.1(4) . . C40 N11 C30 131.2(3) . . C40 N11 C42 105.2(3) . . C42 N11 C30 123.3(3) . . C40 N12 C41 105.4(3) . . F5 B3 F5 111.3(5) . 2_665 F5 B3 N13 111.33(15) . 2_665 F5 B3 N13 108.41(15) . . F5 B3 N13 108.41(15) 2_665 2_665 F5 B3 N13 111.33(15) 2_665 . N13 B3 N13 105.9(4) 2_665 . C44 C43 N14 126.5(4) . . N13 C43 C44 111.6(4) . . N13 C43 N14 121.8(3) . . C43 C44 H44 126.9 . . C45 C44 C43 106.1(4) . . C45 C44 H44 126.9 . . C44 C45 H45 125.8 . . C44 C45 C46 108.3(4) . . C46 C45 H45 125.8 . . C47 C46 C45 131.2(4) . . C47 C46 N13 121.0(4) . . N13 C46 C45 107.7(3) . . C46 C47 C46 119.9(5) 2_665 . C46 C47 C48 120.0(2) . . C46 C47 C48 120.0(2) 2_665 . C49 C48 C47 120.6(3) 2_665 . C49 C48 C47 120.6(3) . . C49 C48 C49 118.8(5) 2_665 . C48 C49 H49 120.1 . . C50 C49 C48 119.8(5) . . C50 C49 H49 120.1 . . C49 C50 H50 119.2 . . C51 C50 C49 121.6(5) . . C51 C50 H50 119.2 . . C50 C51 C50 118.5(6) 2_665 . C50 C51 H51 120.8 2_665 . C50 C51 H51 120.8 . . N14 C52 H52 123.9 . . N15 C52 H52 123.9 . . N15 C52 N14 112.3(5) . . C54 C53 H53 124.5 . . C54 C53 N15 111.0(5) . . N15 C53 H53 124.5 . . C53 C54 H54 127.3 . . C53 C54 N14 105.3(4) . . N14 C54 H54 127.3 . . C43 N13 B3 127.7(3) . . C43 N13 C46 106.2(3) . . C46 N13 B3 126.0(3) . . C52 N14 C43 126.9(4) . . C52 N14 C54 106.9(4) . . C54 N14 C43 126.0(4) . . C52 N15 C53 104.5(4) . . Cl1 C55 Cl2 112.9 . . Cl1 C55 H55A 109.0 . . Cl1 C55 H55B 109.0 . . Cl2 C55 H55A 109.0 . . Cl2 C55 H55B 109.0 . . H55A C55 H55B 107.8 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 B1 F1 1.406(5) . B1 F2 1.377(5) . B1 N1 1.553(5) . B1 N2 1.547(5) . C1 C2 1.401(6) . C1 N1 1.355(5) . C1 N3 1.453(9) . C1 N3B 1.365(9) . C2 H2 0.9500 . C2 C3 1.371(6) . C3 H3 0.9500 . C3 C4 1.411(5) . C4 C5 1.398(5) . C4 N1 1.402(5) . C5 C6 1.407(5) . C5 C10 1.486(5) . C6 C7 1.408(5) . C6 N2 1.392(5) . C7 H7 0.9500 . C7 C8 1.373(5) . C8 H8 0.9500 . C8 C9 1.392(5) . C9 N2 1.360(4) . C9 N5 1.406(5) . C10 C11 1.393(5) . C10 C15 1.394(5) . C11 H11 0.9500 . C11 C12 1.390(6) . C12 H12 0.9500 . C12 C13 1.380(7) . C13 H13 0.9500 . C13 C14 1.380(7) . C14 H14 0.9500 . C14 C15 1.397(6) . C15 H15 0.9500 . C19 H19 0.9500 . C19 N5 1.363(6) . C19 N6 1.310(6) . C20 H20 0.9500 . C20 C21 1.353(7) . C20 N6 1.375(7) . C21 H21 0.9500 . C21 N5 1.390(5) . N3 C18 1.3503 . N3 C16 1.3702 . C18 H18 0.9500 . C18 N4 1.3108 . C16 H16 0.9500 . C16 C17 1.3499 . C17 H17 0.9500 . C17 N4 1.3710 . N3B C18B 1.3495 . N3B C16B 1.3712 . C18B H18B 0.9500 . C18B N4B 1.3087 . C16B H16B 0.9500 . C16B C17B 1.3508 . C17B H17B 0.9500 . C17B N4B 1.3692 . B2 F3 1.400(4) . B2 F4 1.388(4) . B2 N7 1.558(5) . B2 N8 1.550(5) . C22 C23 1.401(5) . C22 N7 1.351(4) . C22 N9 1.395(4) . C23 H23 0.9500 . C23 C24 1.368(5) . C24 H24 0.9500 . C24 C25 1.412(5) . C25 C26 1.387(5) . C25 N7 1.405(4) . C26 C27 1.398(5) . C26 C31 1.495(4) . C27 C28 1.414(5) . C27 N8 1.401(4) . C28 H28 0.9500 . C28 C29 1.376(5) . C29 H29 0.9500 . C29 C30 1.390(5) . C30 N8 1.349(5) . C30 N11 1.401(5) . C31 C32 1.402(5) . C31 C36 1.392(5) . C32 H32 0.9500 . C32 C33 1.385(5) . C33 H33 0.9500 . C33 C34 1.383(6) . C34 H34 0.9500 . C34 C35 1.384(6) . C35 H35 0.9500 . C35 C36 1.402(5) . C36 H36 0.9500 . C37 H37 0.9500 . C37 N9 1.366(6) . C37 N10 1.309(6) . C38 H38 0.9500 . C38 C39 1.315(7) . C38 N10 1.431(8) . C39 H39 0.9500 . C39 N9 1.397(5) . C40 H40 0.9500 . C40 N11 1.375(5) . C40 N12 1.302(5) . C41 H41 0.9500 . C41 C42 1.341(6) . C41 N12 1.362(6) . C42 H42 0.9500 . C42 N11 1.384(5) . B3 F5 1.386(4) 2_665 B3 F5 1.386(4) . B3 N13 1.550(5) . B3 N13 1.550(5) 2_665 C43 C44 1.400(6) . C43 N13 1.346(5) . C43 N14 1.411(5) . C44 H44 0.9500 . C44 C45 1.368(6) . C45 H45 0.9500 . C45 C46 1.413(6) . C46 C47 1.400(5) . C46 N13 1.406(5) . C47 C46 1.400(5) 2_665 C47 C48 1.482(7) . C48 C49 1.397(5) . C48 C49 1.397(5) 2_665 C49 H49 0.9500 . C49 C50 1.388(6) . C50 H50 0.9500 . C50 C51 1.376(7) . C51 C50 1.376(7) 2_665 C51 H51 0.9500 . C52 H52 0.9500 . C52 N14 1.360(6) . C52 N15 1.313(7) . C53 H53 0.9500 . C53 C54 1.361(7) . C53 N15 1.382(7) . C54 H54 0.9500 . C54 N14 1.374(6) . Cl1 C55 1.7603 . Cl2 C55 1.7606 . C55 H55A 0.9900 . C55 H55B 0.9900 .