#------------------------------------------------------------------------------ #$Date: 2020-03-26 04:31:33 +0200 (Thu, 26 Mar 2020) $ #$Revision: 249721 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240200.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_7240200 loop_ _publ_author_name 'Pettersen, Anna' 'Putra, Okky Dwichandra' 'Light, Mark E.' 'Namatame, Yukiko' _publ_section_title ; Invitation to Submit: The Cambridge Structural Database " A peculiar dehydration and solid-solid phase transition of the active pharmaceutical ingredient AZD9898 based on in situ single crystal-to-single crystal transformations " ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00276C _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety '2(C20 H19 Cl F3 N3 O4), 0.5(H2 O)' _chemical_formula_sum 'C40 H39 Cl2 F6 N6 O8.5' _chemical_formula_weight 924.66 _chemical_properties_physical Moisture-sensitive _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_Hall 'P 1' _space_group_name_H-M_alt 'P 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2020-02-07 deposited with the CCDC. 2020-03-24 downloaded from the CCDC. ; _cell_angle_alpha 103.378(3) _cell_angle_beta 105.493(3) _cell_angle_gamma 104.407(3) _cell_formula_units_Z 1 _cell_length_a 9.0757(3) _cell_length_b 11.0502(4) _cell_length_c 11.7199(5) _cell_measurement_reflns_used 10496 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.698 _cell_measurement_theta_min 3.109 _cell_volume 1039.69(8) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)' _computing_data_collection 'CrystalClear-SM Expert 3.1 (Rigaku, 2013)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _diffrn_ambient_pressure 101.3 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Rigaku AFC12 FRE-VHF' _diffrn_measurement_method \w-scan _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_unetI/netI 0.0518 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 25300 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 28.698 _diffrn_reflns_theta_min 3.109 _diffrn_source 'Rotating anode' _diffrn_source_type 'Rotating anode' _exptl_absorpt_coefficient_mu 0.245 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.5638 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.477 _exptl_crystal_description plate _exptl_crystal_F_000 477 _exptl_crystal_recrystallization_method 'the material was recrystallized from --- by slow evaporation' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.339 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.055 _refine_ls_abs_structure_details ; Flack x determined using 3447 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 583 _refine_ls_number_reflns 10496 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0429 _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^)+(0.0596P)^2^+0.0049P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1019 _refine_ls_wR_factor_ref 0.1071 _reflns_Friedel_coverage 0.964 _reflns_Friedel_fraction_full 0.972 _reflns_Friedel_fraction_max 0.961 _reflns_number_gt 8772 _reflns_number_total 10496 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00276c2.cif _cod_data_source_block 2016scas0001_R_100K _cod_original_cell_volume 1039.68(7) _cod_original_formula_sum 'C40 H39 Cl2 F6 N6 O8.50' _cod_database_code 7240200 _shelx_shelxl_version_number 2016/6 _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 ; TITL 2016scas0001_R_100K in P1 #1 2016scas0001_R_100K.res created by SHELXL-2016/6 at 14:37:43 on 17-Nov-2019 REM reset to P1 #1 CELL 0.71073 9.075679 11.050168 11.719946 103.3778 105.4932 104.4071 ZERR 2 0.000334 0.000373 0.000452 0.0031 0.0033 0.0031 LATT -1 SFAC C H Cl F N O UNIT 40 39 2 6 6 8.5 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! EQIV $1 1+X,+Y,1+Z EQIV $2 -1+X,+Y,-1+Z EQIV $3 1+X,1+Y,1+Z DFIX 0.84 O103 H103 DFIX 0.84 O203 H203 L.S. 4 0 0 PLAN 50 TEMP -173(2) HTAB O103 N203_$1 HTAB O203 N103_$2 HTAB O1W O202_$3 BOND fmap 2 53 MORE -1 BOND $H ACTA 52 CONF SHEL 7 0.74 OMIT -1 -2 3 OMIT 0 1 2 OMIT 2 -2 -2 OMIT 1 2 -3 OMIT 3 4 -3 OMIT 0 -1 -2 OMIT 0 -2 -1 OMIT 1 5 -4 OMIT 1 3 -3 OMIT -2 2 2 OMIT 0 0 -2 REM REM REM WGHT 0.059600 0.004900 FVAR 0.72213 CL11 3 0.403754 -0.405557 -0.017815 11.00000 0.03244 0.01294 = 0.02110 0.00071 0.00208 0.00948 F101 4 0.124337 -0.376267 0.048946 11.00000 0.02900 0.01491 = 0.02616 0.00634 0.00910 -0.00179 F102 4 0.259975 0.080208 0.127213 11.00000 0.02041 0.01620 = 0.02447 0.00188 0.01035 0.00774 F103 4 0.242176 0.027218 -0.140617 11.00000 0.01503 0.02420 = 0.02475 0.01022 0.00115 0.00184 O101 6 0.831669 0.534151 0.260833 11.00000 0.01953 0.01318 = 0.01819 0.00334 0.00568 0.00058 O102 6 0.852076 0.621785 0.509835 11.00000 0.04415 0.01704 = 0.02216 0.00174 0.00399 0.01141 O103 6 0.955846 0.359892 0.813130 11.00000 0.02061 0.02168 = 0.01789 0.00602 0.00332 0.00669 O104 6 0.730198 0.386178 0.842648 11.00000 0.02723 0.05091 = 0.02235 0.01072 0.01172 0.01380 N101 5 0.529642 0.095067 0.058795 11.00000 0.01474 0.01175 = 0.01292 0.00316 0.00238 0.00323 N102 5 0.685756 0.315159 0.160395 11.00000 0.01149 0.01405 = 0.01223 0.00171 0.00251 0.00376 N103 5 0.708639 0.278625 0.388692 11.00000 0.01386 0.01495 = 0.01363 0.00151 0.00207 0.00445 C101 1 0.466439 -0.142662 0.026794 11.00000 0.01307 0.01310 = 0.01258 0.00122 0.00231 0.00317 AFIX 43 H101 2 0.560830 -0.141051 0.005735 11.00000 -1.20000 AFIX 0 C102 1 0.363403 -0.260183 0.023234 11.00000 0.02093 0.01156 = 0.01065 -0.00150 -0.00166 0.00450 C103 1 0.225374 -0.261480 0.053503 11.00000 0.02155 0.01289 = 0.01478 0.00470 0.00149 -0.00111 C104 1 0.187036 -0.147761 0.088510 11.00000 0.01677 0.02034 = 0.01580 0.00386 0.00623 0.00382 AFIX 43 H104 2 0.092164 -0.149661 0.108930 11.00000 -1.20000 AFIX 0 C105 1 0.292309 -0.032238 0.092356 11.00000 0.01655 0.01503 = 0.01274 0.00227 0.00261 0.00750 C106 1 0.431180 -0.026050 0.061541 11.00000 0.01356 0.01499 = 0.01065 0.00305 0.00294 0.00369 C107 1 0.528865 0.106345 -0.064092 11.00000 0.01556 0.01664 = 0.01310 0.00295 0.00715 0.00434 AFIX 23 H10A 2 0.539029 0.025061 -0.113545 11.00000 -1.20000 H10B 2 0.624756 0.181060 -0.051784 11.00000 -1.20000 AFIX 0 C108 1 0.376823 0.127405 -0.138514 11.00000 0.01776 0.01644 = 0.01108 0.00479 0.00296 0.00485 C109 1 0.368277 0.104577 -0.273182 11.00000 0.02841 0.03120 = 0.01293 0.00558 0.00345 0.01197 AFIX 137 H10C 2 0.365920 0.014495 -0.309371 11.00000 -1.50000 H10D 2 0.463557 0.167508 -0.276132 11.00000 -1.50000 H10E 2 0.269834 0.116980 -0.321039 11.00000 -1.50000 AFIX 0 C110 1 0.360292 0.258609 -0.079866 11.00000 0.02287 0.01871 = 0.01962 0.00613 0.00529 0.01096 AFIX 137 H11A 2 0.262136 0.266858 -0.133045 11.00000 -1.50000 H11B 2 0.455170 0.330483 -0.071501 11.00000 -1.50000 H11C 2 0.352885 0.263286 0.002853 11.00000 -1.50000 AFIX 0 C111 1 0.614150 0.197348 0.167199 11.00000 0.01184 0.01486 = 0.01013 0.00130 0.00140 0.00577 C112 1 0.761236 0.414969 0.265341 11.00000 0.01132 0.01730 = 0.01596 0.00270 0.00324 0.00661 C113 1 0.773240 0.399226 0.383232 11.00000 0.01232 0.01312 = 0.01659 0.00056 0.00225 0.00205 C114 1 0.627751 0.178313 0.284245 11.00000 0.01704 0.01239 = 0.01300 0.00135 0.00251 0.00117 AFIX 43 H114 2 0.578756 0.093371 0.287994 11.00000 -1.20000 AFIX 0 C115 1 0.815814 0.545911 0.138188 11.00000 0.02291 0.01927 = 0.02640 0.01122 0.01029 0.00422 AFIX 137 H11D 2 0.700827 0.521302 0.088962 11.00000 -1.50000 H11E 2 0.863755 0.487214 0.096096 11.00000 -1.50000 H11F 2 0.872112 0.637190 0.146347 11.00000 -1.50000 AFIX 0 C116 1 0.847313 0.509508 0.504078 11.00000 0.01987 0.01803 = 0.01937 0.00369 0.00424 0.00383 C117 1 0.916467 0.473700 0.618029 11.00000 0.01629 0.01503 = 0.01266 -0.00140 0.00122 0.00109 AFIX 13 H117 2 0.951350 0.394080 0.604850 11.00000 -1.20000 AFIX 0 C118 1 0.848505 0.502846 0.724713 11.00000 0.02254 0.02277 = 0.01503 -0.00032 0.00433 0.00740 AFIX 13 H118 2 0.761648 0.544104 0.711104 11.00000 -1.20000 AFIX 0 C119 1 1.015227 0.586135 0.735960 11.00000 0.02938 0.01857 = 0.01677 -0.00051 0.00031 0.00056 AFIX 23 H11G 2 1.029324 0.676658 0.731997 11.00000 -1.20000 H11H 2 1.110353 0.576321 0.793394 11.00000 -1.20000 AFIX 0 C120 1 0.837174 0.410801 0.798990 11.00000 0.02284 0.02417 = 0.01502 -0.00331 0.00457 0.00618 CL12 3 0.304510 0.918778 0.411088 11.00000 0.02846 0.01342 = 0.02213 0.00147 0.00526 0.00806 F201 4 0.588983 0.889935 0.351747 11.00000 0.02488 0.01569 = 0.02494 0.00447 0.00866 -0.00199 F202 4 0.445725 0.431871 0.265304 11.00000 0.02195 0.01774 = 0.03180 0.00703 0.01277 0.01158 F203 4 0.456093 0.487395 0.536246 11.00000 0.01928 0.03137 = 0.02645 0.01502 0.00332 0.00382 O201 6 -0.134399 -0.021419 0.128602 11.00000 0.01928 0.01449 = 0.02500 0.00395 0.00804 0.00292 O202 6 -0.264589 -0.098682 -0.127430 11.00000 0.02255 0.01603 = 0.02464 0.00080 0.00220 0.00249 N201 5 0.170882 0.417362 0.326752 11.00000 0.01596 0.01302 = 0.01213 0.00272 0.00453 0.00447 N202 5 0.014098 0.197658 0.226473 11.00000 0.01459 0.01649 = 0.01923 0.00597 0.00779 0.00738 N203 5 -0.004121 0.230734 -0.003518 11.00000 0.01304 0.01731 = 0.01512 0.00309 0.00157 0.00473 C201 1 0.237198 0.654538 0.361066 11.00000 0.01582 0.01860 = 0.01225 0.00325 0.00164 0.00788 AFIX 43 H201 2 0.140831 0.652601 0.379186 11.00000 -1.20000 AFIX 0 C202 1 0.344429 0.772842 0.368611 11.00000 0.02059 0.01232 = 0.01045 0.00216 0.00098 0.00546 C203 1 0.485112 0.774511 0.343551 11.00000 0.01844 0.01471 = 0.01123 0.00164 0.00175 0.00028 C204 1 0.523192 0.661722 0.309378 11.00000 0.01508 0.02183 = 0.01542 0.00596 0.00539 0.00490 AFIX 43 H204 2 0.620447 0.663769 0.292659 11.00000 -1.20000 AFIX 0 C205 1 0.412716 0.544898 0.300522 11.00000 0.01848 0.01528 = 0.01580 0.00226 0.00543 0.00739 C206 1 0.272926 0.538842 0.326576 11.00000 0.01549 0.01064 = 0.01052 0.00088 -0.00032 0.00099 C207 1 0.169798 0.406485 0.448887 11.00000 0.01900 0.01408 = 0.01504 0.00426 0.00652 0.00640 AFIX 23 H20A 2 0.072513 0.332631 0.435776 11.00000 -1.20000 H20B 2 0.159974 0.488303 0.497637 11.00000 -1.20000 AFIX 0 C208 1 0.319103 0.383964 0.526065 11.00000 0.01627 0.02096 = 0.02035 0.00873 0.00569 0.00533 C209 1 0.316929 0.401120 0.657902 11.00000 0.03155 0.02708 = 0.01757 0.00989 0.00797 0.01328 AFIX 137 H20C 2 0.415882 0.392512 0.709517 11.00000 -1.50000 H20D 2 0.222164 0.333318 0.655718 11.00000 -1.50000 H20E 2 0.311338 0.488600 0.693546 11.00000 -1.50000 AFIX 0 C210 1 0.338932 0.256011 0.465879 11.00000 0.02568 0.03013 = 0.02358 0.01067 0.00881 0.01730 AFIX 137 H21A 2 0.336077 0.250170 0.380550 11.00000 -1.50000 H21B 2 0.250628 0.182206 0.463491 11.00000 -1.50000 H21C 2 0.443012 0.252284 0.514380 11.00000 -1.50000 AFIX 0 C211 1 0.087511 0.314315 0.218005 11.00000 0.01118 0.01275 = 0.02062 0.00371 0.00596 0.00588 C212 1 -0.065045 0.098753 0.120693 11.00000 0.00910 0.00986 = 0.02248 0.00336 0.00505 0.00213 C213 1 -0.076274 0.111409 0.002181 11.00000 0.01413 0.01858 = 0.01718 0.00336 0.00366 0.00776 C214 1 0.076661 0.331331 0.100274 11.00000 0.01503 0.01517 = 0.01672 0.00632 0.00285 0.00611 AFIX 43 H214 2 0.127724 0.415497 0.095917 11.00000 -1.20000 AFIX 0 C215 1 -0.108865 -0.032458 0.252007 11.00000 0.02485 0.01952 = 0.02766 0.01056 0.00903 0.00545 AFIX 137 H21D 2 -0.172551 -0.121076 0.245687 11.00000 -1.50000 H21E 2 -0.143051 0.033072 0.300608 11.00000 -1.50000 H21F 2 0.006371 -0.016876 0.293641 11.00000 -1.50000 AFIX 0 C216 1 -0.159903 0.001313 -0.117150 11.00000 0.01535 0.01715 = 0.01664 -0.00032 0.00013 0.00959 O203 6 -0.317950 0.158974 -0.436707 11.00000 0.01651 0.01953 = 0.01502 0.00535 0.00210 0.00391 O204 6 -0.084630 0.124885 -0.438141 11.00000 0.01808 0.02921 = 0.02306 0.00213 0.00502 0.00689 C217 1 -0.111816 0.020219 -0.226118 11.00000 0.01608 0.02309 = 0.01668 -0.00023 0.00091 0.00808 AFIX 13 H217 2 -0.003724 0.086837 -0.206719 11.00000 -1.20000 AFIX 0 C218 1 -0.247887 0.008337 -0.342222 11.00000 0.01792 0.01533 = 0.01843 0.00090 -0.00091 0.00200 AFIX 13 H218 2 -0.360040 -0.014268 -0.338797 11.00000 -1.20000 AFIX 0 C219 1 -0.169406 -0.095507 -0.340936 11.00000 0.04077 0.02158 = 0.02185 0.00106 0.00660 0.01571 AFIX 23 H21G 2 -0.233286 -0.181324 -0.338913 11.00000 -1.20000 H21H 2 -0.096935 -0.101248 -0.390398 11.00000 -1.20000 AFIX 0 C220 1 -0.205671 0.102018 -0.410883 11.00000 0.01806 0.01570 = 0.01188 -0.00377 -0.00030 0.00228 H203 2 -0.290112 0.205486 -0.479523 11.00000 -1.50000 H103 2 0.943428 0.316434 0.859551 11.00000 -1.50000 AFIX 6 O1W 6 0.786898 0.701231 0.971836 10.50000 0.12414 0.10533 = 0.11143 0.03619 0.04430 0.05169 H1WA 2 0.751671 0.765998 0.977736 10.50000 -1.50000 H1WB 2 0.707416 0.629545 0.941246 10.50000 -1.50000 REM ##### AFIX 0 HKLF 4 REM 2016scas0001_R_100K in P1 #1 REM R1 = 0.0429 for 8772 Fo > 4sig(Fo) and 0.0563 for all 10496 data REM 583 parameters refined using 5 restraints END WGHT 0.0596 0.0049 REM Highest difference peak 0.339, deepest hole -0.340, 1-sigma level 0.055 Q1 1 0.4406 0.7384 0.6799 11.00000 0.05 0.34 Q2 1 0.8344 0.4546 0.4405 11.00000 0.05 0.31 Q3 1 0.3832 0.1201 -0.2026 11.00000 0.05 0.31 Q4 1 0.3450 -0.0357 0.0550 11.00000 0.05 0.30 Q5 1 0.3298 0.4001 0.5953 11.00000 0.05 0.30 Q6 1 0.3422 0.3229 0.4950 11.00000 0.05 0.30 Q7 1 -0.0761 -0.1843 -0.5813 11.00000 0.05 0.29 Q8 1 0.6313 0.1810 0.2166 11.00000 0.05 0.29 Q9 1 -0.0997 0.0735 -0.0382 11.00000 0.05 0.29 Q10 1 0.2564 -0.2741 -0.0145 11.00000 0.05 0.28 Q11 1 0.3429 0.5496 0.3128 11.00000 0.05 0.28 Q12 1 -0.0493 0.0986 0.0595 11.00000 0.05 0.28 Q13 1 0.1123 0.3167 0.1647 11.00000 0.05 0.28 Q14 1 0.4932 0.0370 0.0681 11.00000 0.05 0.27 Q15 1 0.2967 0.7150 0.3562 11.00000 0.05 0.27 Q16 1 0.7273 0.3638 0.2149 11.00000 0.05 0.27 Q17 1 0.5177 0.1036 -0.0027 11.00000 0.05 0.26 Q18 1 0.4377 0.7872 0.3936 11.00000 0.05 0.26 Q19 1 0.3593 0.1887 -0.1137 11.00000 0.05 0.26 Q20 1 0.7421 0.3474 0.3839 11.00000 0.05 0.25 Q21 1 0.7812 0.4008 0.3207 11.00000 0.05 0.25 Q22 1 0.4014 0.7684 0.3308 11.00000 0.05 0.25 Q23 1 0.2150 0.4833 0.3232 11.00000 0.05 0.25 Q24 1 0.4452 0.1204 -0.1038 11.00000 0.05 0.25 Q25 1 0.2553 0.3994 0.4963 11.00000 0.05 0.25 Q26 1 0.3034 -0.2618 0.0415 11.00000 0.05 0.24 Q27 1 0.4158 -0.1958 0.0397 11.00000 0.05 0.24 Q28 1 0.0752 0.3378 0.1718 11.00000 0.05 0.24 Q29 1 -0.1631 -0.0620 -0.1035 11.00000 0.05 0.24 Q30 1 0.0328 0.1808 0.2863 11.00000 0.05 0.24 Q31 1 0.6590 0.3259 0.1042 11.00000 0.05 0.24 Q32 1 0.4601 0.6054 0.2991 11.00000 0.05 0.23 Q33 1 0.5136 0.7220 0.3461 11.00000 0.05 0.23 Q34 1 -0.0454 0.1607 0.0044 11.00000 0.05 0.22 Q35 1 0.8574 0.4820 0.5600 11.00000 0.05 0.22 Q36 1 0.2958 0.8574 0.3191 11.00000 0.05 0.22 Q37 1 0.1817 0.4112 0.3840 11.00000 0.05 0.22 Q38 1 0.2387 -0.0927 0.0816 11.00000 0.05 0.22 Q39 1 0.1365 0.3583 0.2689 11.00000 0.05 0.22 Q40 1 0.4390 -0.0850 0.0393 11.00000 0.05 0.21 Q41 1 0.1995 0.9347 0.4004 11.00000 0.05 0.21 Q42 1 -0.2188 -0.1183 0.2217 11.00000 0.05 0.21 Q43 1 0.5607 0.1557 0.1222 11.00000 0.05 0.21 Q44 1 -0.0196 0.1544 0.1781 11.00000 0.05 0.21 Q45 1 -0.1481 0.0157 -0.1735 11.00000 0.05 0.21 Q46 1 0.8835 0.5860 0.4953 11.00000 0.05 0.21 Q47 1 0.0120 0.2784 0.0598 11.00000 0.05 0.21 Q48 1 1.2609 0.7766 0.7031 11.00000 0.05 0.21 Q49 1 -0.2222 0.0435 -0.3818 11.00000 0.05 0.20 Q50 1 0.8988 0.2886 0.7009 11.00000 0.05 0.19 ; _shelx_res_checksum 1527 loop_ _space_group_symop_operation_xyz 'x, y, 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 Cl11 Cl 0.40375(10) -0.40556(8) -0.01781(8) 0.0242(2) Uani 1 1 d . . . . . F101 F 0.1243(3) -0.3763(2) 0.0489(2) 0.0253(5) Uani 1 1 d . . . . . F102 F 0.2600(2) 0.08021(19) 0.12721(19) 0.0203(5) Uani 1 1 d . . . . . F103 F 0.2422(2) 0.0272(2) -0.1406(2) 0.0230(5) Uani 1 1 d . . . . . O101 O 0.8317(3) 0.5342(2) 0.2608(2) 0.0184(5) Uani 1 1 d . . . . . O102 O 0.8521(3) 0.6218(2) 0.5098(2) 0.0300(6) Uani 1 1 d . . . . . O103 O 0.9558(3) 0.3599(2) 0.8131(2) 0.0209(5) Uani 1 1 d D . . . . O104 O 0.7302(3) 0.3862(3) 0.8426(2) 0.0328(6) Uani 1 1 d . . . . . N101 N 0.5296(3) 0.0951(3) 0.0588(3) 0.0140(6) Uani 1 1 d . . . . . N102 N 0.6858(3) 0.3152(3) 0.1604(3) 0.0135(6) Uani 1 1 d . . . . . N103 N 0.7086(3) 0.2786(3) 0.3887(3) 0.0153(6) Uani 1 1 d . . . . . C101 C 0.4664(4) -0.1427(3) 0.0268(3) 0.0141(7) Uani 1 1 d . . . . . H101 H 0.560830 -0.141051 0.005735 0.017 Uiso 1 1 calc R U . . . C102 C 0.3634(4) -0.2602(3) 0.0232(3) 0.0170(7) Uani 1 1 d . . . . . C103 C 0.2254(4) -0.2615(3) 0.0535(3) 0.0187(8) Uani 1 1 d . . . . . C104 C 0.1870(4) -0.1478(4) 0.0885(3) 0.0183(7) Uani 1 1 d . . . . . H104 H 0.092164 -0.149661 0.108930 0.022 Uiso 1 1 calc R U . . . C105 C 0.2923(4) -0.0322(3) 0.0924(3) 0.0152(7) Uani 1 1 d . . . . . C106 C 0.4312(4) -0.0261(4) 0.0615(3) 0.0137(7) Uani 1 1 d . . . . . C107 C 0.5289(4) 0.1063(3) -0.0641(3) 0.0152(7) Uani 1 1 d . . . . . H10A H 0.539029 0.025061 -0.113545 0.018 Uiso 1 1 calc R U . . . H10B H 0.624756 0.181060 -0.051784 0.018 Uiso 1 1 calc R U . . . C108 C 0.3768(4) 0.1274(3) -0.1385(3) 0.0156(7) Uani 1 1 d . . . . . C109 C 0.3683(5) 0.1046(4) -0.2732(4) 0.0248(8) Uani 1 1 d . . . . . H10C H 0.365920 0.014495 -0.309371 0.037 Uiso 1 1 calc R U . . . H10D H 0.463557 0.167508 -0.276132 0.037 Uiso 1 1 calc R U . . . H10E H 0.269834 0.116980 -0.321039 0.037 Uiso 1 1 calc R U . . . C110 C 0.3603(4) 0.2586(4) -0.0799(4) 0.0200(8) Uani 1 1 d . . . . . H11A H 0.262136 0.266858 -0.133045 0.030 Uiso 1 1 calc R U . . . H11B H 0.455170 0.330483 -0.071501 0.030 Uiso 1 1 calc R U . . . H11C H 0.352885 0.263286 0.002853 0.030 Uiso 1 1 calc R U . . . C111 C 0.6141(4) 0.1973(3) 0.1672(3) 0.0130(6) Uani 1 1 d . . . . . C112 C 0.7612(4) 0.4150(4) 0.2653(3) 0.0153(7) Uani 1 1 d . . . . . C113 C 0.7732(4) 0.3992(3) 0.3832(3) 0.0158(7) Uani 1 1 d . . . . . C114 C 0.6278(4) 0.1783(3) 0.2842(3) 0.0159(7) Uani 1 1 d . . . . . H114 H 0.578756 0.093371 0.287994 0.019 Uiso 1 1 calc R U . . . C115 C 0.8158(4) 0.5459(4) 0.1382(4) 0.0223(8) Uani 1 1 d . . . . . H11D H 0.700827 0.521302 0.088962 0.033 Uiso 1 1 calc R U . . . H11E H 0.863755 0.487214 0.096096 0.033 Uiso 1 1 calc R U . . . H11F H 0.872112 0.637190 0.146347 0.033 Uiso 1 1 calc R U . . . C116 C 0.8473(4) 0.5095(4) 0.5041(3) 0.0205(8) Uani 1 1 d . . . . . C117 C 0.9165(4) 0.4737(3) 0.6180(3) 0.0174(6) Uani 1 1 d . . . . . H117 H 0.951350 0.394080 0.604850 0.021 Uiso 1 1 calc R U . . . C118 C 0.8485(4) 0.5028(3) 0.7247(3) 0.0218(7) Uani 1 1 d . . . . . H118 H 0.761648 0.544104 0.711104 0.026 Uiso 1 1 calc R U . . . C119 C 1.0152(4) 0.5861(3) 0.7360(3) 0.0258(7) Uani 1 1 d . . . . . H11G H 1.029324 0.676658 0.731997 0.031 Uiso 1 1 calc R U . . . H11H H 1.110353 0.576321 0.793394 0.031 Uiso 1 1 calc R U . . . C120 C 0.8372(4) 0.4108(4) 0.7990(3) 0.0232(7) Uani 1 1 d . . . . . Cl12 Cl 0.30451(10) 0.91878(8) 0.41109(8) 0.0226(2) Uani 1 1 d . . . . . F201 F 0.5890(2) 0.8899(2) 0.3517(2) 0.0239(5) Uani 1 1 d . . . . . F202 F 0.4457(2) 0.4319(2) 0.2653(2) 0.0222(5) Uani 1 1 d . . . . . F203 F 0.4561(2) 0.4874(2) 0.5362(2) 0.0265(5) Uani 1 1 d . . . . . O201 O -0.1344(3) -0.0214(2) 0.1286(2) 0.0205(6) Uani 1 1 d . . . . . O202 O -0.2646(3) -0.0987(2) -0.1274(2) 0.0242(5) Uani 1 1 d . . . . . N201 N 0.1709(3) 0.4174(3) 0.3268(3) 0.0141(6) Uani 1 1 d . . . . . N202 N 0.0141(3) 0.1977(3) 0.2265(3) 0.0159(6) Uani 1 1 d . . . . . N203 N -0.0041(3) 0.2307(3) -0.0035(3) 0.0163(6) Uani 1 1 d . . . . . C201 C 0.2372(4) 0.6545(4) 0.3611(3) 0.0161(7) Uani 1 1 d . . . . . H201 H 0.140831 0.652601 0.379186 0.019 Uiso 1 1 calc R U . . . C202 C 0.3444(4) 0.7728(3) 0.3686(3) 0.0157(7) Uani 1 1 d . . . . . C203 C 0.4851(4) 0.7745(3) 0.3436(3) 0.0170(7) Uani 1 1 d . . . . . C204 C 0.5232(4) 0.6617(4) 0.3094(3) 0.0177(7) Uani 1 1 d . . . . . H204 H 0.620447 0.663769 0.292659 0.021 Uiso 1 1 calc R U . . . C205 C 0.4127(4) 0.5449(3) 0.3005(3) 0.0168(7) Uani 1 1 d . . . . . C206 C 0.2729(4) 0.5388(3) 0.3266(3) 0.0144(7) Uani 1 1 d . . . . . C207 C 0.1698(4) 0.4065(3) 0.4489(3) 0.0158(7) Uani 1 1 d . . . . . H20A H 0.072513 0.332631 0.435776 0.019 Uiso 1 1 calc R U . . . H20B H 0.159974 0.488303 0.497637 0.019 Uiso 1 1 calc R U . . . C208 C 0.3191(4) 0.3840(4) 0.5261(4) 0.0191(7) Uani 1 1 d . . . . . C209 C 0.3169(5) 0.4011(4) 0.6579(4) 0.0243(8) Uani 1 1 d . . . . . H20C H 0.415882 0.392512 0.709517 0.036 Uiso 1 1 calc R U . . . H20D H 0.222164 0.333318 0.655718 0.036 Uiso 1 1 calc R U . . . H20E H 0.311338 0.488600 0.693546 0.036 Uiso 1 1 calc R U . . . C210 C 0.3389(5) 0.2560(4) 0.4659(4) 0.0244(8) Uani 1 1 d . . . . . H21A H 0.336077 0.250170 0.380550 0.037 Uiso 1 1 calc R U . . . H21B H 0.250628 0.182206 0.463491 0.037 Uiso 1 1 calc R U . . . H21C H 0.443012 0.252284 0.514380 0.037 Uiso 1 1 calc R U . . . C211 C 0.0875(4) 0.3143(3) 0.2180(3) 0.0147(7) Uani 1 1 d . . . . . C212 C -0.0650(4) 0.0988(3) 0.1207(3) 0.0144(7) Uani 1 1 d . . . . . C213 C -0.0763(4) 0.1114(4) 0.0022(3) 0.0170(7) Uani 1 1 d . . . . . C214 C 0.0767(4) 0.3313(3) 0.1003(3) 0.0158(7) Uani 1 1 d . . . . . H214 H 0.127724 0.415497 0.095917 0.019 Uiso 1 1 calc R U . . . C215 C -0.1089(5) -0.0325(4) 0.2520(4) 0.0238(8) Uani 1 1 d . . . . . H21D H -0.172551 -0.121076 0.245687 0.036 Uiso 1 1 calc R U . . . H21E H -0.143051 0.033072 0.300608 0.036 Uiso 1 1 calc R U . . . H21F H 0.006371 -0.016876 0.293641 0.036 Uiso 1 1 calc R U . . . C216 C -0.1599(4) 0.0013(4) -0.1172(3) 0.0178(7) Uani 1 1 d . . . . . O203 O -0.3180(3) 0.1590(2) -0.4367(2) 0.0182(5) Uani 1 1 d D . . . . O204 O -0.0846(3) 0.1249(3) -0.4381(2) 0.0252(5) Uani 1 1 d . . . . . C217 C -0.1118(4) 0.0202(3) -0.2261(3) 0.0205(6) Uani 1 1 d . . . . . H217 H -0.003724 0.086837 -0.206719 0.025 Uiso 1 1 calc R U . . . C218 C -0.2479(4) 0.0083(3) -0.3422(3) 0.0203(6) Uani 1 1 d . . . . . H218 H -0.360040 -0.014268 -0.338797 0.024 Uiso 1 1 calc R U . . . C219 C -0.1694(5) -0.0955(3) -0.3409(3) 0.0290(8) Uani 1 1 d . . . . . H21G H -0.233286 -0.181324 -0.338913 0.035 Uiso 1 1 calc R U . . . H21H H -0.096935 -0.101248 -0.390398 0.035 Uiso 1 1 calc R U . . . C220 C -0.2057(4) 0.1020(3) -0.4109(3) 0.0186(6) Uani 1 1 d . . . . . H203 H -0.290(5) 0.205(4) -0.480(4) 0.028 Uiso 1 1 d D U . . . H103 H 0.943(5) 0.316(4) 0.860(4) 0.028 Uiso 1 1 d D U . . . O1W O 0.7869(14) 0.7012(12) 0.9718(13) 0.110(4) Uani 0.5 1 d G . P . . H1WA H 0.751671 0.765998 0.977736 0.165 Uiso 0.5 1 d G U P . . H1WB H 0.707416 0.629545 0.941246 0.165 Uiso 0.5 1 d G U P . . 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 Cl11 0.0324(5) 0.0129(4) 0.0211(5) 0.0007(3) 0.0021(4) 0.0095(4) F101 0.0290(11) 0.0149(11) 0.0262(12) 0.0063(9) 0.0091(9) -0.0018(9) F102 0.0204(10) 0.0162(11) 0.0245(12) 0.0019(9) 0.0103(9) 0.0077(9) F103 0.0150(10) 0.0242(12) 0.0247(12) 0.0102(10) 0.0011(9) 0.0018(9) O101 0.0195(12) 0.0132(13) 0.0182(14) 0.0033(11) 0.0057(10) 0.0006(10) O102 0.0442(16) 0.0170(11) 0.0222(13) 0.0017(10) 0.0040(12) 0.0114(11) O103 0.0206(12) 0.0217(13) 0.0179(13) 0.0060(10) 0.0033(10) 0.0067(10) O104 0.0272(14) 0.0509(17) 0.0223(14) 0.0107(12) 0.0117(12) 0.0138(13) N101 0.0147(14) 0.0117(15) 0.0129(15) 0.0032(12) 0.0024(11) 0.0032(11) N102 0.0115(13) 0.0141(15) 0.0122(15) 0.0017(12) 0.0025(11) 0.0038(11) N103 0.0139(13) 0.0149(15) 0.0136(15) 0.0015(12) 0.0021(11) 0.0044(12) C101 0.0131(15) 0.0131(17) 0.0126(17) 0.0012(13) 0.0023(13) 0.0032(13) C102 0.0209(17) 0.0116(17) 0.0107(18) -0.0015(14) -0.0017(14) 0.0045(14) C103 0.0215(18) 0.0129(18) 0.0148(19) 0.0047(15) 0.0015(14) -0.0011(14) C104 0.0168(16) 0.0203(19) 0.0158(18) 0.0039(15) 0.0062(14) 0.0038(14) C105 0.0166(16) 0.0150(18) 0.0127(18) 0.0023(14) 0.0026(14) 0.0075(14) C106 0.0136(15) 0.0150(17) 0.0107(17) 0.0031(13) 0.0029(13) 0.0037(13) C107 0.0156(16) 0.0166(18) 0.0131(17) 0.0030(14) 0.0072(14) 0.0043(14) C108 0.0178(16) 0.0164(18) 0.0111(17) 0.0048(14) 0.0030(14) 0.0048(14) C109 0.028(2) 0.031(2) 0.0129(19) 0.0056(16) 0.0035(15) 0.0120(17) C110 0.0229(18) 0.0187(19) 0.020(2) 0.0061(15) 0.0053(15) 0.0110(15) C111 0.0118(15) 0.0149(17) 0.0101(16) 0.0013(13) 0.0014(13) 0.0058(13) C112 0.0113(15) 0.0173(18) 0.0160(18) 0.0027(14) 0.0032(13) 0.0066(13) C113 0.0123(15) 0.0131(17) 0.0166(19) 0.0006(14) 0.0022(13) 0.0021(13) C114 0.0170(16) 0.0124(17) 0.0130(17) 0.0014(13) 0.0025(13) 0.0012(13) C115 0.0229(19) 0.019(2) 0.026(2) 0.0112(17) 0.0103(17) 0.0042(16) C116 0.0199(17) 0.0180(19) 0.019(2) 0.0037(15) 0.0042(14) 0.0038(14) C117 0.0163(15) 0.0150(14) 0.0127(15) -0.0014(11) 0.0012(12) 0.0011(12) C118 0.0225(16) 0.0228(16) 0.0150(16) -0.0003(12) 0.0043(13) 0.0074(13) C119 0.0294(18) 0.0186(16) 0.0168(17) -0.0005(13) 0.0003(14) 0.0006(14) C120 0.0228(18) 0.0242(18) 0.0150(17) -0.0033(13) 0.0046(14) 0.0062(15) Cl12 0.0285(5) 0.0134(4) 0.0221(5) 0.0015(3) 0.0053(4) 0.0081(3) F201 0.0249(11) 0.0157(11) 0.0249(12) 0.0045(9) 0.0087(9) -0.0020(9) F202 0.0219(11) 0.0177(11) 0.0318(13) 0.0070(10) 0.0128(10) 0.0116(9) F203 0.0193(10) 0.0314(13) 0.0264(13) 0.0150(10) 0.0033(9) 0.0038(9) O201 0.0193(13) 0.0145(13) 0.0250(15) 0.0039(11) 0.0080(11) 0.0029(10) O202 0.0225(12) 0.0160(11) 0.0246(13) 0.0008(9) 0.0022(10) 0.0025(9) N201 0.0160(14) 0.0130(15) 0.0121(15) 0.0027(12) 0.0045(11) 0.0045(11) N202 0.0146(14) 0.0165(16) 0.0192(16) 0.0060(13) 0.0078(12) 0.0074(12) N203 0.0130(14) 0.0173(16) 0.0151(15) 0.0031(12) 0.0016(11) 0.0047(12) C201 0.0158(16) 0.0186(19) 0.0122(17) 0.0032(14) 0.0016(13) 0.0079(14) C202 0.0206(17) 0.0123(17) 0.0104(17) 0.0022(14) 0.0010(14) 0.0055(14) C203 0.0184(17) 0.0147(18) 0.0112(18) 0.0016(14) 0.0018(14) 0.0003(14) C204 0.0151(16) 0.0218(19) 0.0154(18) 0.0060(15) 0.0054(14) 0.0049(14) C205 0.0185(17) 0.0153(18) 0.0158(19) 0.0023(15) 0.0054(14) 0.0074(15) C206 0.0155(16) 0.0106(16) 0.0105(17) 0.0009(13) -0.0003(13) 0.0010(13) C207 0.0190(17) 0.0141(17) 0.0150(18) 0.0043(14) 0.0065(14) 0.0064(14) C208 0.0163(17) 0.021(2) 0.020(2) 0.0087(15) 0.0057(15) 0.0053(15) C209 0.0315(19) 0.027(2) 0.0176(19) 0.0099(16) 0.0080(16) 0.0133(17) C210 0.0257(19) 0.030(2) 0.024(2) 0.0107(17) 0.0088(16) 0.0173(17) C211 0.0112(15) 0.0128(17) 0.0206(19) 0.0037(14) 0.0060(14) 0.0059(13) C212 0.0091(14) 0.0099(16) 0.0225(19) 0.0034(14) 0.0050(13) 0.0021(12) C213 0.0141(16) 0.0186(19) 0.0172(19) 0.0034(15) 0.0037(14) 0.0078(14) C214 0.0150(16) 0.0152(17) 0.0167(18) 0.0063(14) 0.0028(14) 0.0061(14) C215 0.025(2) 0.020(2) 0.028(2) 0.0106(18) 0.0090(17) 0.0055(16) C216 0.0154(16) 0.0171(18) 0.0166(18) -0.0003(14) 0.0001(13) 0.0096(14) O203 0.0165(11) 0.0195(12) 0.0150(12) 0.0053(9) 0.0021(9) 0.0039(9) O204 0.0181(12) 0.0292(14) 0.0231(14) 0.0021(11) 0.0050(10) 0.0069(11) C217 0.0161(15) 0.0231(16) 0.0167(16) -0.0002(12) 0.0009(12) 0.0081(13) C218 0.0179(16) 0.0153(15) 0.0184(17) 0.0009(12) -0.0009(13) 0.0020(13) C219 0.041(2) 0.0216(17) 0.0219(18) 0.0011(13) 0.0066(16) 0.0157(16) C220 0.0181(16) 0.0157(15) 0.0119(15) -0.0038(12) -0.0003(13) 0.0023(13) O1W 0.124(9) 0.105(8) 0.111(10) 0.036(8) 0.044(8) 0.052(8) 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' 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' O O 0.0106 0.0060 '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 _geom_angle_publ_flag C112 O101 C115 116.7(3) . . ? C120 O103 H103 106(3) . . ? C111 N101 C106 119.9(3) . . ? C111 N101 C107 122.5(3) . . ? C106 N101 C107 117.6(3) . . ? C112 N102 C111 118.2(3) . . ? C114 N103 C113 119.9(3) . . ? C102 C101 C106 119.8(3) . . ? C102 C101 H101 120.1 . . ? C106 C101 H101 120.1 . . ? C101 C102 C103 119.6(3) . . ? C101 C102 Cl11 121.1(3) . . ? C103 C102 Cl11 119.3(3) . . ? F101 C103 C104 118.4(3) . . ? F101 C103 C102 119.5(3) . . ? C104 C103 C102 122.1(3) . . ? C105 C104 C103 117.1(3) . . ? C105 C104 H104 121.5 . . ? C103 C104 H104 121.5 . . ? F102 C105 C104 118.7(3) . . ? F102 C105 C106 118.3(3) . . ? C104 C105 C106 123.0(3) . . ? C105 C106 C101 118.4(3) . . ? C105 C106 N101 120.4(3) . . ? C101 C106 N101 121.0(3) . . ? N101 C107 C108 113.8(3) . . ? N101 C107 H10A 108.8 . . ? C108 C107 H10A 108.8 . . ? N101 C107 H10B 108.8 . . ? C108 C107 H10B 108.8 . . ? H10A C107 H10B 107.7 . . ? F103 C108 C110 107.0(3) . . ? F103 C108 C109 106.3(3) . . ? C110 C108 C109 113.0(3) . . ? F103 C108 C107 106.8(3) . . ? C110 C108 C107 113.6(3) . . ? C109 C108 C107 109.6(3) . . ? C108 C109 H10C 109.5 . . ? C108 C109 H10D 109.5 . . ? H10C C109 H10D 109.5 . . ? C108 C109 H10E 109.5 . . ? H10C C109 H10E 109.5 . . ? H10D C109 H10E 109.5 . . ? C108 C110 H11A 109.5 . . ? C108 C110 H11B 109.5 . . ? H11A C110 H11B 109.5 . . ? C108 C110 H11C 109.5 . . ? H11A C110 H11C 109.5 . . ? H11B C110 H11C 109.5 . . ? N102 C111 N101 118.6(3) . . ? N102 C111 C114 120.7(3) . . ? N101 C111 C114 120.7(3) . . ? N102 C112 O101 119.4(3) . . ? N102 C112 C113 122.1(3) . . ? O101 C112 C113 118.5(3) . . ? N103 C113 C112 118.8(3) . . ? N103 C113 C116 116.7(3) . . ? C112 C113 C116 124.5(3) . . ? N103 C114 C111 120.1(3) . . ? N103 C114 H114 119.9 . . ? C111 C114 H114 119.9 . . ? O101 C115 H11D 109.5 . . ? O101 C115 H11E 109.5 . . ? H11D C115 H11E 109.5 . . ? O101 C115 H11F 109.5 . . ? H11D C115 H11F 109.5 . . ? H11E C115 H11F 109.5 . . ? O102 C116 C113 122.0(3) . . ? O102 C116 C117 122.0(3) . . ? C113 C116 C117 116.0(3) . . ? C119 C117 C116 116.4(3) . . ? C119 C117 C118 59.8(2) . . ? C116 C117 C118 117.6(3) . . ? C119 C117 H117 116.9 . . ? C116 C117 H117 116.9 . . ? C118 C117 H117 116.9 . . ? C120 C118 C119 118.4(3) . . ? C120 C118 C117 118.3(3) . . ? C119 C118 C117 58.7(2) . . ? C120 C118 H118 116.4 . . ? C119 C118 H118 116.4 . . ? C117 C118 H118 116.4 . . ? C117 C119 C118 61.4(2) . . ? C117 C119 H11G 117.6 . . ? C118 C119 H11G 117.6 . . ? C117 C119 H11H 117.6 . . ? C118 C119 H11H 117.6 . . ? H11G C119 H11H 114.7 . . ? O104 C120 O103 123.9(3) . . ? O104 C120 C118 123.0(3) . . ? O103 C120 C118 113.0(3) . . ? C212 O201 C215 117.1(3) . . ? C211 N201 C206 120.7(3) . . ? C211 N201 C207 122.4(3) . . ? C206 N201 C207 116.7(3) . . ? C212 N202 C211 117.1(3) . . ? C214 N203 C213 120.1(3) . . ? C202 C201 C206 119.1(3) . . ? C202 C201 H201 120.4 . . ? C206 C201 H201 120.4 . . ? C203 C202 C201 119.9(3) . . ? C203 C202 Cl12 119.6(3) . . ? C201 C202 Cl12 120.5(2) . . ? F201 C203 C204 118.4(3) . . ? F201 C203 C202 119.5(3) . . ? C204 C203 C202 122.2(3) . . ? C203 C204 C205 116.7(3) . . ? C203 C204 H204 121.6 . . ? C205 C204 H204 121.6 . . ? F202 C205 C206 118.8(3) . . ? F202 C205 C204 118.1(3) . . ? C206 C205 C204 123.1(3) . . ? C205 C206 C201 119.0(3) . . ? C205 C206 N201 120.6(3) . . ? C201 C206 N201 120.3(3) . . ? N201 C207 C208 114.9(3) . . ? N201 C207 H20A 108.5 . . ? C208 C207 H20A 108.5 . . ? N201 C207 H20B 108.5 . . ? C208 C207 H20B 108.5 . . ? H20A C207 H20B 107.5 . . ? F203 C208 C210 107.3(3) . . ? F203 C208 C209 106.2(3) . . ? C210 C208 C209 113.7(3) . . ? F203 C208 C207 106.7(3) . . ? C210 C208 C207 113.4(3) . . ? C209 C208 C207 108.9(3) . . ? C208 C209 H20C 109.5 . . ? C208 C209 H20D 109.5 . . ? H20C C209 H20D 109.5 . . ? C208 C209 H20E 109.5 . . ? H20C C209 H20E 109.5 . . ? H20D C209 H20E 109.5 . . ? C208 C210 H21A 109.5 . . ? C208 C210 H21B 109.5 . . ? H21A C210 H21B 109.5 . . ? C208 C210 H21C 109.5 . . ? H21A C210 H21C 109.5 . . ? H21B C210 H21C 109.5 . . ? N202 C211 N201 117.8(3) . . ? N202 C211 C214 121.0(3) . . ? N201 C211 C214 121.2(3) . . ? N202 C212 O201 117.6(3) . . ? N202 C212 C213 123.5(3) . . ? O201 C212 C213 118.9(3) . . ? N203 C213 C212 118.0(3) . . ? N203 C213 C216 117.5(3) . . ? C212 C213 C216 124.4(3) . . ? N203 C214 C211 120.3(3) . . ? N203 C214 H214 119.8 . . ? C211 C214 H214 119.8 . . ? O201 C215 H21D 109.5 . . ? O201 C215 H21E 109.5 . . ? H21D C215 H21E 109.5 . . ? O201 C215 H21F 109.5 . . ? H21D C215 H21F 109.5 . . ? H21E C215 H21F 109.5 . . ? O202 C216 C213 122.3(3) . . ? O202 C216 C217 121.4(3) . . ? C213 C216 C217 116.3(3) . . ? C220 O203 H203 106(3) . . ? C219 C217 C216 118.3(3) . . ? C219 C217 C218 59.4(2) . . ? C216 C217 C218 116.3(3) . . ? C219 C217 H217 116.8 . . ? C216 C217 H217 116.8 . . ? C218 C217 H217 116.8 . . ? C220 C218 C219 118.6(3) . . ? C220 C218 C217 115.8(3) . . ? C219 C218 C217 59.0(2) . . ? C220 C218 H218 116.9 . . ? C219 C218 H218 116.9 . . ? C217 C218 H218 116.9 . . ? C217 C219 C218 61.6(2) . . ? C217 C219 H21G 117.6 . . ? C218 C219 H21G 117.6 . . ? C217 C219 H21H 117.6 . . ? C218 C219 H21H 117.6 . . ? H21G C219 H21H 114.7 . . ? O204 C220 O203 124.3(3) . . ? O204 C220 C218 124.7(3) . . ? O203 C220 C218 111.0(3) . . ? H1WA O1W H1WB 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl11 C102 1.725(3) . ? F101 C103 1.348(4) . ? F102 C105 1.344(4) . ? F103 C108 1.420(4) . ? O101 C112 1.333(4) . ? O101 C115 1.445(4) . ? O102 C116 1.216(4) . ? O103 C120 1.324(4) . ? O103 H103 0.82(2) . ? O104 C120 1.215(4) . ? N101 C111 1.365(4) . ? N101 C106 1.425(4) . ? N101 C107 1.472(4) . ? N102 C112 1.321(4) . ? N102 C111 1.333(4) . ? N103 C114 1.324(4) . ? N103 C113 1.340(4) . ? C101 C102 1.383(5) . ? C101 C106 1.400(5) . ? C101 H101 0.9500 . ? C102 C103 1.388(5) . ? C103 C104 1.387(5) . ? C104 C105 1.374(5) . ? C104 H104 0.9500 . ? C105 C106 1.391(5) . ? C107 C108 1.526(5) . ? C107 H10A 0.9900 . ? C107 H10B 0.9900 . ? C108 C110 1.516(5) . ? C108 C109 1.517(5) . ? C109 H10C 0.9800 . ? C109 H10D 0.9800 . ? C109 H10E 0.9800 . ? C110 H11A 0.9800 . ? C110 H11B 0.9800 . ? C110 H11C 0.9800 . ? C111 C114 1.413(5) . ? C112 C113 1.411(5) . ? C113 C116 1.493(5) . ? C114 H114 0.9500 . ? C115 H11D 0.9800 . ? C115 H11E 0.9800 . ? C115 H11F 0.9800 . ? C116 C117 1.501(5) . ? C117 C119 1.499(4) . ? C117 C118 1.540(4) . ? C117 H117 1.0000 . ? C118 C120 1.486(5) . ? C118 C119 1.516(5) . ? C118 H118 1.0000 . ? C119 H11G 0.9900 . ? C119 H11H 0.9900 . ? Cl12 C202 1.731(3) . ? F201 C203 1.350(4) . ? F202 C205 1.354(4) . ? F203 C208 1.420(4) . ? O201 C212 1.357(4) . ? O201 C215 1.441(5) . ? O202 C216 1.222(4) . ? N201 C211 1.370(5) . ? N201 C206 1.429(4) . ? N201 C207 1.466(4) . ? N202 C212 1.324(5) . ? N202 C211 1.335(4) . ? N203 C214 1.321(5) . ? N203 C213 1.344(5) . ? C201 C202 1.390(5) . ? C201 C206 1.393(5) . ? C201 H201 0.9500 . ? C202 C203 1.381(5) . ? C203 C204 1.375(5) . ? C204 C205 1.386(5) . ? C204 H204 0.9500 . ? C205 C206 1.372(5) . ? C207 C208 1.528(5) . ? C207 H20A 0.9900 . ? C207 H20B 0.9900 . ? C208 C210 1.504(5) . ? C208 C209 1.519(5) . ? C209 H20C 0.9800 . ? C209 H20D 0.9800 . ? C209 H20E 0.9800 . ? C210 H21A 0.9800 . ? C210 H21B 0.9800 . ? C210 H21C 0.9800 . ? C211 C214 1.416(5) . ? C212 C213 1.407(5) . ? C213 C216 1.483(5) . ? C214 H214 0.9500 . ? C215 H21D 0.9800 . ? C215 H21E 0.9800 . ? C215 H21F 0.9800 . ? C216 C217 1.497(5) . ? O203 C220 1.330(4) . ? O203 H203 0.84(2) . ? O204 C220 1.208(4) . ? C217 C219 1.488(4) . ? C217 C218 1.527(4) . ? C217 H217 1.0000 . ? C218 C220 1.490(5) . ? C218 C219 1.494(4) . ? C218 H218 1.0000 . ? C219 H21G 0.9900 . ? C219 H21H 0.9900 . ? O1W H1WA 0.8497 . ? O1W H1WB 0.8500 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O103 H103 N203 0.82(2) 2.05(3) 2.837(4) 161(4) 1_656 O203 H203 N103 0.84(2) 1.90(3) 2.711(4) 162(4) 1_454 O1W H1WA O202 0.85 2.15 2.806(12) 133.3 1_666 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C106 C101 C102 C103 0.4(5) . . . . ? C106 C101 C102 Cl11 -179.4(3) . . . . ? C101 C102 C103 F101 179.4(3) . . . . ? Cl11 C102 C103 F101 -0.8(5) . . . . ? C101 C102 C103 C104 -0.5(5) . . . . ? Cl11 C102 C103 C104 179.3(3) . . . . ? F101 C103 C104 C105 180.0(3) . . . . ? C102 C103 C104 C105 -0.1(5) . . . . ? C103 C104 C105 F102 -179.3(3) . . . . ? C103 C104 C105 C106 0.8(5) . . . . ? F102 C105 C106 C101 179.2(3) . . . . ? C104 C105 C106 C101 -1.0(5) . . . . ? F102 C105 C106 N101 -4.3(5) . . . . ? C104 C105 C106 N101 175.5(3) . . . . ? C102 C101 C106 C105 0.3(5) . . . . ? C102 C101 C106 N101 -176.2(3) . . . . ? C111 N101 C106 C105 67.6(4) . . . . ? C107 N101 C106 C105 -109.3(4) . . . . ? C111 N101 C106 C101 -116.0(4) . . . . ? C107 N101 C106 C101 67.1(4) . . . . ? C111 N101 C107 C108 -100.8(3) . . . . ? C106 N101 C107 C108 76.1(4) . . . . ? N101 C107 C108 F103 -51.5(4) . . . . ? N101 C107 C108 C110 66.2(4) . . . . ? N101 C107 C108 C109 -166.3(3) . . . . ? C112 N102 C111 N101 177.1(3) . . . . ? C112 N102 C111 C114 -4.0(4) . . . . ? C106 N101 C111 N102 -170.2(3) . . . . ? C107 N101 C111 N102 6.6(4) . . . . ? C106 N101 C111 C114 10.8(4) . . . . ? C107 N101 C111 C114 -172.4(3) . . . . ? C111 N102 C112 O101 -179.0(3) . . . . ? C111 N102 C112 C113 2.5(4) . . . . ? C115 O101 C112 N102 1.7(4) . . . . ? C115 O101 C112 C113 -179.8(3) . . . . ? C114 N103 C113 C112 -3.6(5) . . . . ? C114 N103 C113 C116 173.7(3) . . . . ? N102 C112 C113 N103 1.3(5) . . . . ? O101 C112 C113 N103 -177.2(3) . . . . ? N102 C112 C113 C116 -175.8(3) . . . . ? O101 C112 C113 C116 5.7(5) . . . . ? C113 N103 C114 C111 2.1(5) . . . . ? N102 C111 C114 N103 1.8(5) . . . . ? N101 C111 C114 N103 -179.3(3) . . . . ? N103 C113 C116 O102 -151.0(3) . . . . ? C112 C113 C116 O102 26.2(5) . . . . ? N103 C113 C116 C117 29.4(4) . . . . ? C112 C113 C116 C117 -153.4(3) . . . . ? O102 C116 C117 C119 -9.6(5) . . . . ? C113 C116 C117 C119 170.1(3) . . . . ? O102 C116 C117 C118 58.5(5) . . . . ? C113 C116 C117 C118 -121.8(3) . . . . ? C119 C117 C118 C120 -107.8(3) . . . . ? C116 C117 C118 C120 146.0(3) . . . . ? C116 C117 C118 C119 -106.1(3) . . . . ? C116 C117 C119 C118 108.0(3) . . . . ? C120 C118 C119 C117 107.5(3) . . . . ? C119 C118 C120 O104 145.7(3) . . . . ? C117 C118 C120 O104 -146.5(3) . . . . ? C119 C118 C120 O103 -33.8(4) . . . . ? C117 C118 C120 O103 34.0(4) . . . . ? C206 C201 C202 C203 -0.8(5) . . . . ? C206 C201 C202 Cl12 180.0(3) . . . . ? C201 C202 C203 F201 -179.6(3) . . . . ? Cl12 C202 C203 F201 -0.4(5) . . . . ? C201 C202 C203 C204 0.8(5) . . . . ? Cl12 C202 C203 C204 -180.0(3) . . . . ? F201 C203 C204 C205 -179.3(3) . . . . ? C202 C203 C204 C205 0.3(5) . . . . ? C203 C204 C205 F202 179.1(3) . . . . ? C203 C204 C205 C206 -1.4(5) . . . . ? F202 C205 C206 C201 -179.1(3) . . . . ? C204 C205 C206 C201 1.4(6) . . . . ? F202 C205 C206 N201 5.2(5) . . . . ? C204 C205 C206 N201 -174.3(3) . . . . ? C202 C201 C206 C205 -0.3(5) . . . . ? C202 C201 C206 N201 175.5(3) . . . . ? C211 N201 C206 C205 -67.9(4) . . . . ? C207 N201 C206 C205 107.9(4) . . . . ? C211 N201 C206 C201 116.4(4) . . . . ? C207 N201 C206 C201 -67.8(4) . . . . ? C211 N201 C207 C208 99.9(3) . . . . ? C206 N201 C207 C208 -75.9(4) . . . . ? N201 C207 C208 F203 54.9(4) . . . . ? N201 C207 C208 C210 -63.1(4) . . . . ? N201 C207 C208 C209 169.2(3) . . . . ? C212 N202 C211 N201 -179.5(3) . . . . ? C212 N202 C211 C214 1.7(4) . . . . ? C206 N201 C211 N202 170.1(3) . . . . ? C207 N201 C211 N202 -5.5(4) . . . . ? C206 N201 C211 C214 -11.1(4) . . . . ? C207 N201 C211 C214 173.3(3) . . . . ? C211 N202 C212 O201 177.3(3) . . . . ? C211 N202 C212 C213 -0.7(4) . . . . ? C215 O201 C212 N202 -3.1(4) . . . . ? C215 O201 C212 C213 175.0(3) . . . . ? C214 N203 C213 C212 1.1(4) . . . . ? C214 N203 C213 C216 -177.8(3) . . . . ? N202 C212 C213 N203 -0.7(5) . . . . ? O201 C212 C213 N203 -178.7(3) . . . . ? N202 C212 C213 C216 178.1(3) . . . . ? O201 C212 C213 C216 0.1(5) . . . . ? C213 N203 C214 C211 -0.1(4) . . . . ? N202 C211 C214 N203 -1.3(5) . . . . ? N201 C211 C214 N203 179.9(3) . . . . ? N203 C213 C216 O202 -159.1(3) . . . . ? C212 C213 C216 O202 22.1(5) . . . . ? N203 C213 C216 C217 19.6(4) . . . . ? C212 C213 C216 C217 -159.2(3) . . . . ? O202 C216 C217 C219 -12.1(5) . . . . ? C213 C216 C217 C219 169.2(3) . . . . ? O202 C216 C217 C218 55.6(4) . . . . ? C213 C216 C217 C218 -123.1(3) . . . . ? C219 C217 C218 C220 -109.3(3) . . . . ? C216 C217 C218 C220 142.0(3) . . . . ? C216 C217 C218 C219 -108.7(3) . . . . ? C216 C217 C219 C218 105.5(3) . . . . ? C220 C218 C219 C217 104.6(3) . . . . ? C219 C218 C220 O204 -20.5(5) . . . . ? C217 C218 C220 O204 46.7(4) . . . . ? C219 C218 C220 O203 160.5(3) . . . . ? C217 C218 C220 O203 -132.3(3) . . . . ?