#------------------------------------------------------------------------------ #$Date: 2024-10-21 10:25:28 +0300 (Mon, 21 Oct 2024) $ #$Revision: 295565 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/28/1572876.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_1572876 loop_ _publ_author_name 'Hawash, Mohammed' 'Al-Smadi, Derar' 'Kumar, Anil' 'Olech, Barbara' 'Dominiak, Paulina Maria' 'Jaradat, Nidal' 'Antari, Sarah' 'Mohammed, Sarah' 'Nasasrh, Alaa' 'Abualhasan, Murad' 'Musa, Ahmed' 'Suboh, Shorooq' '\,Capan, \.Irfan' 'Qneibi, Mohammad' 'Natsheh, Hiba' _publ_section_title ; Characterization and Investigation of Novel Benzodioxol Derivatives as Antidiabetic Agents: An In Vitro and In Vivo Study in an Animal Model ; _journal_issue 10 _journal_name_full Biomolecules _journal_page_first 1486 _journal_paper_doi 10.3390/biom13101486 _journal_volume 13 _journal_year 2023 _chemical_absolute_configuration unk _chemical_formula_moiety 'C15 H10 F3 N O3' _chemical_formula_sum 'C15 H10 F3 N O3' _chemical_formula_weight 309.243 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _symmetry_Int_Tables_number 9 _atom_sites_solution_primary dual _audit_creation_date 2023-08-09 _audit_creation_method ; Olex2 1.5-alpha (compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535) ; _cell_angle_alpha 90 _cell_angle_beta 91.9 _cell_angle_gamma 90.000(1) _cell_formula_units_Z 4 _cell_length_a 7.1000(1) _cell_length_b 6.8000(1) _cell_length_c 24.300(1) _cell_measurement_reflns_used 4279 _cell_measurement_temperature 81.15 _cell_measurement_theta_max 1.03 _cell_measurement_theta_min 0.12 _cell_volume 1172.56(5) _computing_molecular_graphics 'Olex2 1.5-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'olex2.refine 1.5-alpha (Bourhis et al., 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 81.15 _diffrn_measured_fraction_theta_full 0.7433 _diffrn_measured_fraction_theta_max 0.7453 _diffrn_measurement_device_type 'ThermoFisher 200kV Glacios TEM with CetaD CMOS' _diffrn_radiation_type electron _diffrn_radiation_wavelength 0.02508 _diffrn_reflns_av_R_equivalents 0.1044 _diffrn_reflns_av_unetI/netI 0.1689 _diffrn_reflns_Laue_measured_fraction_full 0.7433 _diffrn_reflns_Laue_measured_fraction_max 0.7453 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 4279 _diffrn_reflns_point_group_measured_fraction_full 0.7324 _diffrn_reflns_point_group_measured_fraction_max 0.7291 _diffrn_reflns_theta_full 0.8622 _diffrn_reflns_theta_max 1.03 _diffrn_reflns_theta_min 0.12 _exptl_absorpt_coefficient_mu 0.000 _exptl_crystal_density_diffrn 1.752 _exptl_crystal_description Plate _exptl_crystal_F_000 222.136 _refine_diff_density_max 0.171 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.0400 _refine_ls_abs_structure_details 'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.' _refine_ls_abs_structure_Flack 1(23) _refine_ls_d_res_high 0.6968 _refine_ls_d_res_low 6.0717 _refine_ls_extinction_coef 3209(789) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_goodness_of_fit_ref 0.9891 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 21 _refine_ls_number_parameters 188 _refine_ls_number_reflns 2619 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 0.9891 _refine_ls_R_factor_all 0.1349 _refine_ls_R_factor_gt 0.1060 _refine_ls_shift/su_max 0.0007 _refine_ls_shift/su_mean 0.0002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1721P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2691 _refine_ls_wR_factor_ref 0.2939 _reflns_Friedel_coverage 0.713 _reflns_limit_h_max 9 _reflns_limit_h_min -9 _reflns_limit_k_max 9 _reflns_limit_k_min -9 _reflns_limit_l_max 34 _reflns_limit_l_min -34 _reflns_number_gt 1702 _reflns_number_total 2619 _reflns_threshold_expression I>=2u(I) _iucr_refine_instructions_details ; TITL ssa11_2_a.res in Cc REM Old TITL SSA11_2 REM SHELXT solution in Cc: R1 0.222, Rweak 0.083, Alpha 0.014 REM 0.000 for 0 systematic absences, Orientation as input REM Flack x = -1.427 ( 2.549 ) from 598 Parsons' quotients REM Formula found by SHELXT: C17 N O F3 CELL 0.02508 7.1 6.8 24.3 90 91.9 90 ZERR 4 0.0001 0.0001 0.001 0 0 0.001 LATT -7 SYMM +X,-Y,0.5+Z SFAC C 0.731 36.995 1.195 11.297 0.456 2.814 0.125 0.346 0 0 0 0 0.77 12.011 SFAC H 0.375 15.495 0.141 4.126 0.022 0.025 -0.101 46.884 0 0 0 0 0.32 1.008 SFAC F 0.369 20.239 0.811 6.609 0.475 1.931 0.146 0.279 0 0 0 0 0.72 18.998 SFAC N 0.572 28.846 1.042 9.054 0.465 2.421 0.131 0.317 0 0 0 0 0.75 14.007 SFAC O 0.455 23.78 0.917 7.622 0.472 2.144 0.138 0.296 0 0 0 0 0.73 15.999 UNIT 60 40 12 4 12 EADP C11 C10 EADP C5 C8 L.S. 10 PLAN 20 TEMP -192 CONF BOND FMAP 2 list 3 MORE -1 BOND $H ACTA EXTI 3208.691374 WGHT 0.172085 0 FVAR 4.372745 REM REM REM C8 1 0.48918 0.38302 0.52751 11.00000 0.02300 0.02157 0.01359 = -0.00379 0.00968 -0.00520 F3 3 0.56467 0.30020 0.28555 11.00000 0.05731 0.03904 0.01310 = 0.00364 0.00738 -0.00297 O1 5 0.60751 0.49583 0.51065 11.00000 0.05053 0.02042 0.01776 = -0.00898 0.01893 -0.01878 F1 3 0.73979 0.47522 0.33633 11.00000 0.05200 0.02064 0.02175 = -0.00053 0.02330 -0.01054 C4 1 0.31571 0.29375 0.61160 11.00000 0.03296 0.01401 0.02021 = -0.00075 0.01864 0.00609 AFIX 43 1.083 H4 2 0.32604 0.14052 0.59993 11.00000 -1.20000 AFIX 0 F2 3 0.85516 0.23282 0.29714 11.00000 0.04327 0.03483 0.02510 = -0.00117 0.02191 0.00828 C6 1 0.37009 0.62673 0.59074 11.00000 0.03257 0.02000 0.01475 = -0.00222 0.01169 -0.00572 AFIX 43 1.083 H6 2 0.42296 0.74066 0.56420 11.00000 -1.20000 AFIX 0 O2 5 0.25627 0.84762 0.65970 11.00000 0.03945 0.01670 0.02145 = 0.00191 0.00593 0.00627 N1 4 0.44845 0.21598 0.50478 11.00000 0.04128 0.02160 0.00598 = -0.00025 0.00867 -0.00185 AFIX 43 1.027 H1 2 0.34758 0.13136 0.52272 11.00000 -1.20000 AFIX 0 O3 5 0.14680 0.61532 0.71644 11.00000 0.05276 0.03096 0.01459 = -0.00102 0.01958 0.01055 C9 1 0.53085 0.14132 0.45769 11.00000 0.02938 0.01021 0.00958 = 0.00105 0.00744 -0.00363 C15 1 0.70306 0.29594 0.32249 11.00000 0.04552 0.01970 0.00885 = 0.00383 0.01065 0.00021 C7 1 0.28526 0.67287 0.63832 11.00000 0.02272 0.01736 0.01335 = -0.00243 0.00435 -0.00441 C10 1 0.58828 0.25740 0.41627 11.00000 0.04573 0.01754 0.01065 = -0.00173 0.01490 0.00011 AFIX 43 1.083 H10 2 0.57607 0.41577 0.41922 11.00000 -1.20000 AFIX 0 C2 1 0.21955 0.53326 0.67220 11.00000 0.02761 0.02368 0.01380 = 0.00019 0.01390 0.00709 C5 1 0.38680 0.43334 0.57733 11.00000 0.02300 0.02157 0.01359 = -0.00379 0.00968 -0.00520 C13 1 0.62591 -0.13941 0.40864 11.00000 0.04460 0.01309 0.01721 = -0.00132 0.01423 0.00287 AFIX 43 1.083 H13 2 0.64207 -0.29758 0.40657 11.00000 -1.20000 AFIX 0 C3 1 0.23212 0.33943 0.65999 11.00000 0.04743 0.01715 0.01245 = -0.00040 0.01394 -0.00382 AFIX 43 1.083 H3 2 0.17910 0.22691 0.68695 11.00000 -1.20000 AFIX 0 C11 1 0.66250 0.17236 0.37026 11.00000 0.04573 0.01754 0.01065 = -0.00173 0.01490 0.00011 C12 1 0.68365 -0.02423 0.36605 11.00000 0.02901 0.02144 0.01658 = -0.00240 0.01035 -0.00328 AFIX 43 1.083 H12 2 0.74453 -0.08924 0.33004 11.00000 -1.20000 AFIX 0 C14 1 0.54789 -0.05546 0.45379 11.00000 0.03630 0.01439 0.01180 = -0.00215 0.01079 -0.00298 AFIX 43 1.083 H14 2 0.49943 -0.14821 0.48667 11.00000 -1.20000 AFIX 0 C1 1 0.18802 0.81222 0.71244 11.00000 0.04294 0.02247 0.01842 = -0.00086 0.00989 0.00387 AFIX 23 1.091 H1a 2 0.29418 0.85320 0.74385 11.00000 -1.20000 H1b 2 0.06168 0.89967 0.71867 11.00000 -1.20000 AFIX 0 HKLF 4 END Q1 1 0.291667 0.166667 0.506173 11 0.05 0.15 Q2 1 0.458333 0.541667 0.518519 11 0.05 0.14 Q3 1 0.666667 0 0.512346 11 0.05 0.14 Q4 1 0.666667 0.125 0.283951 11 0.05 0.13 Q5 1 0.333333 0.583333 0.709877 11 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.1060 for 1702 Fo > 4sig(Fo) and 0.1349 for all 2619 data REM 188 parameters refined using 2 restraints REM Highest difference peak 0.1524, deepest hole -0.1478 REM Mean Shift 0.0002, Max Shift 0.0007. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1349 REM R1_gt = 0.1060 REM wR_ref = 0.2939 REM GOOF = 0.9891 REM Shift_max = 0.0007 REM Shift_mean = 0.0002 REM Reflections_all = 2619 REM Reflections_gt = 1702 REM Parameters = 188 REM Hole = -0.159 REM Peak = 0.171 REM Flack = 1(23) ; _cod_data_source_file SSA11_final_file001.cif _cod_data_source_block SSA11_2 _cod_depositor_comments ;loop _audit_support was added The loop audit_support has been corrected ; _cod_original_sg_symbol_Hall ' C -2yc' _cod_database_code 1572876 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C11) = Uanis(C10) Uanis(C5) = Uanis(C8) 3.a Secondary CH2 refined with riding coordinates: C1(H1a,H1b) 3.b Aromatic/amide H refined with riding coordinates: C4(H4), C6(H6), N1(H1), C10(H10), C13(H13), C3(H3), C12(H12), C14(H14) ; _iucr_refine_fcf_details ; data_SSA11_2 _computing_structure_refinement 'olex2.refine 1.5 (Bourhis et al., 2015)' _shelx_refln_list_code 4 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 x,-y,z+1/2 3 x+1/2,y+1/2,z 4 x+1/2,-y+1/2,z+1/2 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_H-M_alt 'C 1 c 1' _space_group_name_Hall ' C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _symmetry_space_group_name_Hall ' C -2yc' _symmetry_Int_Tables_number 9 _cell_length_a 7.1000(1) _cell_length_b 6.8000(1) _cell_length_c 24.300(1) _cell_angle_alpha 90 _cell_angle_beta 91.9 _cell_angle_gamma 90.000(1) _cell_volume 1172.56(5) loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_F_squared_weight _refln_observed_status -9 1 6 0.355 -0.604 2.381 78.482 o -9 1 7 4.518 0.924 2.341 76.664 o -9 1 8 4.747 -0.017 2.529 66.528 o -9 1 9 6.763 0.713 2.295 74.995 o -9 1 10 2.282 -0.590 2.059 103.345 o -9 1 11 0.222 0.426 2.181 93.578 o -9 1 12 0.107 0.951 2.149 96.282 o -9 1 13 2.135 0.398 2.070 102.177 o -9 1 14 0.625 0.396 2.104 100.390 o -9 1 15 0.071 0.397 1.939 118.358 o -9 3 4 0.146 0.515 1.921 120.624 o -9 3 5 0.284 -0.196 2.025 108.576 o -9 3 6 0.132 1.057 2.022 108.732 o -9 3 7 0.199 -0.004 1.996 111.684 o -9 3 8 1.811 2.212 2.373 77.484 o -9 3 9 0.980 0.480 2.075 102.891 o -9 3 10 0.166 -0.007 2.024 108.650 o -9 3 11 0.006 -0.344 1.781 140.391 o -9 3 12 0.428 0.178 4.163 25.685 o -8 0 8 22.218 14.682 4.422 14.335 o -8 0 10 10.063 10.465 3.963 23.694 o -8 0 12 9.325 8.784 3.851 25.722 o -8 0 14 0.391 0.573 2.671 62.344 o -8 0 16 1.432 1.774 2.661 62.265 o -8 0 18 5.738 3.392 3.004 45.646 o -8 0 20 3.447 -0.456 2.957 50.013 o -8 2 5 0.443 0.447 2.187 92.938 o -8 2 6 3.818 3.261 2.530 65.529 o -8 2 7 12.263 18.643 4.126 19.224 o -8 2 8 0.009 2.232 2.559 67.801 o -8 2 9 7.271 4.886 6.669 9.737 o -8 2 10 3.452 3.219 2.193 86.481 o -8 2 11 8.176 4.508 4.591 19.779 o -8 2 12 2.126 1.583 1.908 118.585 o -8 2 13 7.451 2.531 2.010 88.314 o -8 2 14 4.687 2.661 2.048 95.271 o -8 2 15 2.290 0.723 2.011 107.597 o -8 2 16 3.638 2.387 1.968 106.543 o -8 2 17 0.040 1.063 2.077 103.072 o -8 2 18 4.382 1.883 2.074 95.229 o -8 2 19 0.331 1.651 2.012 109.459 o -8 2 20 1.498 0.155 1.896 122.710 o -8 4 2 1.405 0.754 1.578 175.838 o -8 4 3 6.257 4.003 1.995 91.241 o -8 4 4 2.435 2.271 1.807 129.667 o -8 4 5 4.425 4.713 2.152 84.998 o -8 4 6 0.720 3.997 2.099 98.822 o -8 4 7 5.358 7.099 2.387 66.026 o -8 4 8 0.978 2.933 1.962 113.289 o -8 4 9 1.159 0.445 1.722 148.815 o -8 4 10 0.871 1.185 1.930 118.558 o -8 4 11 2.851 0.638 1.685 149.825 o -8 4 12 0.052 -0.853 1.673 159.014 o -8 4 13 0.494 0.046 1.843 130.902 o -8 4 14 0.004 0.935 1.835 132.115 o -8 4 15 0.190 -0.109 1.876 126.486 o -8 4 16 0.959 1.257 2.141 96.391 o -7 -5 0 2.658 0.843 1.361 225.032 o -7 -1 -23 0.354 -0.591 1.345 245.901 o -7 1 5 0.601 1.207 2.107 99.873 o -7 1 6 12.108 10.084 3.085 33.245 o -7 1 7 24.632 32.374 5.688 8.200 o -7 1 8 11.681 9.921 2.348 48.605 o -7 1 9 12.441 12.850 2.747 36.395 o -7 1 10 31.814 33.117 4.345 8.961 o -7 1 11 47.001 41.785 7.841 3.645 o -7 1 12 0.676 1.442 1.785 138.563 o -7 1 13 3.446 6.827 2.670 57.464 o -7 1 14 16.774 20.913 3.285 21.659 o -7 1 15 6.050 6.116 2.159 77.370 o -7 1 16 0.469 2.751 1.952 115.532 o -7 1 17 2.657 2.720 1.918 114.450 o -7 1 18 5.601 7.257 5.738 13.078 o -7 1 19 2.320 2.165 1.995 107.687 o -7 1 20 3.330 2.479 2.134 92.189 o -7 1 21 1.187 1.750 1.982 111.736 o -7 1 22 6.716 6.433 3.764 28.781 o -7 1 23 10.715 6.678 2.432 52.294 o -7 1 24 0.057 1.159 2.095 101.311 o -7 1 25 1.638 0.875 2.167 93.646 o -7 3 3 0.710 0.995 1.891 123.797 o -7 3 4 4.265 4.556 2.202 82.257 o -7 3 6 4.144 8.671 2.899 47.606 o -7 3 7 1.885 7.555 2.668 59.021 o -7 3 8 0.505 2.410 1.955 115.371 o -7 3 9 4.368 6.462 2.377 69.469 o -7 3 10 3.314 5.789 4.393 22.479 o -7 3 11 1.840 2.763 1.946 113.503 o -7 3 12 8.715 9.548 4.231 21.934 o -7 3 13 2.837 1.844 1.951 111.543 o -7 3 14 2.719 2.835 2.085 97.341 o -7 3 15 0.007 3.273 2.660 62.586 o -7 3 16 0.772 1.418 1.838 130.724 o -7 3 17 0.545 1.707 1.736 146.487 o -7 3 18 0.581 1.228 1.741 145.927 o -7 3 19 7.140 2.795 1.895 97.822 o -7 3 20 4.236 3.505 2.093 91.745 o -7 3 21 0.296 0.385 1.810 135.800 o -7 3 22 1.724 0.760 1.761 140.942 o -7 3 23 0.110 0.895 1.993 111.982 o -7 5 1 1.554 2.986 1.542 178.102 o -7 5 2 0.127 1.741 1.554 183.251 o -7 5 3 20.495 25.491 4.257 13.627 o -7 5 4 12.556 19.343 3.489 23.836 o -7 5 5 3.403 2.357 1.539 168.375 o -7 5 6 0.323 0.369 1.375 235.215 o -7 5 7 0.543 2.923 1.774 139.105 o -7 5 8 2.032 4.598 1.892 116.304 o -7 5 9 4.772 4.821 2.126 85.659 o -7 5 10 1.745 2.242 1.846 126.585 o -7 5 11 0.637 5.507 2.066 100.682 o -7 5 12 0.660 1.542 1.657 160.526 o -7 5 13 2.228 2.896 3.163 43.728 o -7 5 14 0.296 1.202 1.638 165.215 o -7 5 15 0.158 0.492 1.656 162.113 o -7 5 16 2.071 2.253 1.749 139.404 o -7 5 17 1.835 1.355 1.846 127.535 o -6 -6 -2 6.558 5.007 1.410 145.124 o -6 -6 -1 26.539 27.420 4.165 11.511 o -6 -6 0 0.328 2.062 1.259 276.648 o -6 -4 -23 0.985 1.111 3.072 47.010 o -6 -4 -22 0.536 1.485 1.416 219.592 o -6 -4 -21 0.624 -0.198 1.416 221.348 o -6 -4 -20 1.167 1.148 1.838 130.181 o -6 -4 -19 0.594 1.700 1.911 120.977 o -6 -4 -18 1.360 1.477 1.676 155.322 o -6 -2 -26 0.757 0.917 2.330 81.741 o -6 -2 -25 0.677 0.031 1.470 205.363 o -6 -2 -24 0.031 -0.377 1.554 184.403 o -6 -2 -23 0.691 0.947 1.781 139.596 o -6 -2 -22 2.869 2.494 1.924 113.417 o -6 -2 -21 2.424 2.941 1.940 112.298 o -6 -2 -20 0.153 0.973 2.381 78.430 o -6 -2 -19 0.405 0.864 2.314 83.007 o -6 0 -24 1.789 1.301 2.428 74.501 o -6 0 -22 2.477 1.756 2.721 58.958 o -6 0 -20 0.526 0.769 2.604 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4.403 1.750 136.274 o 6 -2 -13 39.575 56.102 10.027 2.770 o 6 -2 -12 13.767 13.168 2.375 40.126 o 6 -2 -11 39.549 45.669 5.122 5.747 o 6 -2 -10 14.194 11.220 2.160 45.293 o 6 -2 -9 3.719 2.405 1.485 176.347 o 6 -2 -8 5.238 3.588 1.652 131.658 o 6 -2 -7 1.005 0.686 2.422 75.575 o 6 -2 -6 2.748 2.439 2.584 64.654 o 6 -2 -4 12.259 9.649 3.085 33.320 o 6 0 -28 1.335 0.209 2.541 68.639 o 6 0 -26 9.399 4.776 2.732 47.913 o 6 0 -24 31.252 30.251 5.463 7.655 o 6 0 -22 7.603 13.259 3.382 31.566 o 6 0 -20 13.081 8.742 2.755 38.374 o 6 0 -18 21.682 29.281 5.238 9.938 o 6 0 -16 4.254 6.774 2.829 50.768 o 6 0 -14 33.535 38.797 6.354 5.762 o 6 0 -12 112.664 160.876 22.387 0.449 o 6 0 -10 36.543 57.199 8.908 3.293 o 6 0 -8 26.935 37.355 6.604 6.271 o 6 0 -6 53.895 77.252 11.545 1.810 o 6 0 22 2.477 -0.104 3.633 33.516 o 6 0 24 1.789 0.632 3.754 31.464 o 6 0 26 2.640 -1.079 3.164 44.058 o 6 2 21 2.424 -0.337 3.145 44.646 o 6 2 22 2.869 -0.954 2.443 73.248 o 6 2 23 0.691 -0.248 2.520 70.031 o 6 2 24 0.031 -0.815 2.339 81.338 o 6 2 25 0.677 0.625 2.227 89.538 o 6 2 26 0.757 -0.471 3.358 39.458 o 6 4 20 1.167 -0.394 2.559 67.788 o 6 4 21 0.624 0.410 2.411 76.457 o 6 4 22 0.536 0.006 2.353 80.381 o 6 4 23 0.985 1.203 3.568 34.887 o 6 6 0 0.328 1.923 1.896 123.027 o 6 6 1 26.539 28.154 4.632 10.313 o 7 -5 -18 0.231 1.118 2.346 80.747 o 7 -5 -17 1.835 2.214 2.081 100.154 o 7 -5 -16 2.071 0.671 1.524 185.657 o 7 -5 -15 0.158 -0.455 1.487 201.284 o 7 -5 -14 0.296 0.693 1.467 206.323 o 7 -5 -13 2.228 5.209 3.122 44.272 o 7 -5 -12 0.660 0.885 2.119 98.766 o 7 -5 -11 0.637 1.073 2.156 95.408 o 7 -5 -9 4.772 13.217 3.085 39.663 o 7 -5 -8 2.032 4.732 2.214 86.300 o 7 -5 -7 0.543 4.601 2.105 98.144 o 7 -5 -6 0.323 0.231 1.757 144.032 o 7 -5 -5 3.403 4.008 2.409 71.939 o 7 -5 -4 12.556 18.599 3.916 20.586 o 7 -5 -3 20.495 16.352 3.588 18.786 o 7 -5 -2 0.127 10.076 2.873 51.734 o 7 -5 -1 1.554 1.427 2.057 103.603 o 7 -3 -23 0.110 0.584 1.733 148.128 o 7 -3 -22 1.724 1.390 1.626 163.586 o 7 -3 -21 0.296 0.008 1.541 187.461 o 7 -3 -20 4.236 5.978 2.278 75.771 o 7 -3 -19 7.140 5.924 2.914 45.273 o 7 -3 -18 0.581 2.493 1.664 158.229 o 7 -3 -17 0.545 0.677 1.620 169.012 o 7 -3 -16 0.772 1.248 1.679 156.513 o 7 -3 -15 0.007 0.713 1.763 143.150 o 7 -3 -14 2.719 2.109 1.824 126.620 o 7 -3 -13 2.837 1.815 1.566 168.798 o 7 -3 -12 8.715 11.592 7.647 7.269 o 7 -3 -11 1.840 3.635 1.682 148.174 o 7 -3 -10 3.314 6.329 1.882 108.764 o 7 -3 -9 4.368 7.361 2.588 58.944 o 7 -3 -8 0.505 0.674 2.201 91.729 o 7 -3 -7 1.885 4.448 2.802 55.128 o 7 -3 -6 4.144 12.003 3.633 30.582 o 7 -3 -4 4.265 3.893 2.668 58.357 o 7 -3 -3 0.710 1.646 2.205 90.978 o 7 -1 -25 1.638 1.519 1.876 123.789 o 7 -1 -24 0.057 -0.175 1.744 146.308 o 7 -1 -23 10.715 11.532 3.612 26.780 o 7 -1 -22 6.716 12.612 5.169 15.376 o 7 -1 -21 1.187 3.208 1.803 132.725 o 7 -1 -20 3.330 4.423 1.898 111.104 o 7 -1 -19 2.320 5.863 4.575 20.903 o 7 -1 -18 5.601 5.628 2.009 89.633 o 7 -1 -17 2.657 1.482 1.703 145.845 o 7 -1 -16 0.469 3.126 1.768 139.963 o 7 -1 -15 6.050 5.833 1.945 91.984 o 7 -1 -14 16.774 17.586 2.855 26.570 o 7 -1 -13 3.446 2.114 2.231 84.909 o 7 -1 -12 0.676 1.627 1.776 139.797 o 7 -1 -11 47.001 52.909 13.461 1.765 o 7 -1 -10 31.814 35.830 9.817 3.453 o 7 -1 -9 12.441 18.184 2.917 30.466 o 7 -1 -8 11.681 17.405 4.768 15.783 o 7 -1 -7 24.632 35.598 6.121 7.278 o 7 -1 -6 12.108 6.346 2.702 42.900 o 8 -4 -16 0.959 1.755 1.877 124.842 o 8 -4 -15 0.190 1.010 1.660 161.168 o 8 -4 -14 0.004 0.895 1.507 195.746 o 8 -4 -13 0.494 -0.178 1.488 200.680 o 8 -4 -12 0.052 1.172 2.023 108.686 o 8 -4 -11 2.851 0.843 1.993 108.212 o 8 -4 -10 0.871 3.644 2.472 71.712 o 8 -4 -9 1.159 2.418 2.445 73.553 o 8 -4 -8 0.978 0.430 2.295 84.259 o 8 -4 -7 5.358 5.922 2.862 48.895 o 8 -4 -6 0.720 3.175 2.568 66.821 o 8 -4 -5 4.425 3.688 2.612 60.653 o 8 -4 -4 2.435 3.106 2.401 74.505 o 8 -4 -3 6.257 10.234 3.041 40.657 o 8 -2 -20 1.498 0.051 1.797 136.512 o 8 -2 -19 0.331 4.396 3.550 35.095 o 8 -2 -18 4.382 5.694 3.994 26.756 o 8 -2 -17 0.040 0.085 1.733 148.158 o 8 -2 -16 3.638 3.490 1.975 103.990 o 8 -2 -15 2.290 2.343 1.833 126.498 o 8 -2 -14 4.687 1.889 1.800 121.772 o 8 -2 -13 7.451 9.813 4.074 23.929 o 8 -2 -12 2.126 3.808 2.583 64.655 o 8 -2 -11 8.176 6.296 2.156 70.248 o 8 -2 -10 3.452 6.163 2.199 82.504 o 8 -2 -9 7.271 7.123 3.088 40.180 o 8 -2 -8 0.009 1.714 2.548 68.457 o 8 -2 -7 12.263 16.447 3.927 21.255 o 8 -2 -6 3.818 4.608 2.674 58.255 o 8 -2 -5 0.443 0.788 2.192 92.475 o 8 0 -20 3.447 2.912 2.653 60.538 o 8 0 -18 5.738 7.474 2.978 44.294 o 8 0 -16 1.432 2.000 2.554 67.447 o 8 0 -14 0.391 0.587 2.422 75.803 o 8 0 -12 9.325 12.476 3.851 24.707 o 8 0 -10 10.063 9.982 3.395 30.683 o 8 0 -8 22.218 30.434 5.751 8.641 o 9 -3 -12 0.428 1.268 2.600 65.687 o 9 -3 -11 0.006 0.180 2.487 71.975 o 9 -3 -10 0.166 3.390 2.666 62.242 o 9 -3 -9 0.980 -0.488 2.425 75.557 o 9 -3 -8 1.811 3.127 2.836 54.325 o 9 -3 -7 0.199 5.306 2.889 52.675 o 9 -3 -6 0.132 2.266 2.441 74.453 o 9 -3 -5 0.284 0.486 2.177 93.876 o 9 -1 -16 2.436 3.094 2.139 93.038 o 9 -1 -15 0.071 1.180 1.880 125.804 o 9 -1 -14 0.625 1.516 1.877 125.445 o 9 -1 -13 2.135 1.605 1.864 124.127 o 9 -1 -12 0.107 1.521 1.898 123.297 o 9 -1 -11 0.222 2.392 1.900 122.369 o 9 -1 -10 2.282 4.461 2.296 80.393 o 9 -1 -9 6.763 7.545 3.285 36.343 o 9 -1 -8 4.747 4.947 2.894 49.132 o ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 x,-y,z+1/2 3 x+1/2,y+1/2,z 4 x+1/2,-y+1/2,z+1/2 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_refinement_flags_posn C8 C 0.4892(10) 0.3830(8) 0.5275(2) 0.0192(12) Uani 1.000000 . F3 F 0.5647(10) 0.3002(8) 0.28555(18) 0.0363(17) Uani 1.000000 . O1 O 0.6075(9) 0.4958(7) 0.51065(18) 0.0292(15) Uani 1.000000 . F1 F 0.7398(8) 0.4752(6) 0.33633(17) 0.0310(15) Uani 1.000000 . C4 C 0.3157(10) 0.2937(8) 0.6116(2) 0.0220(16) Uani 1.000000 . H4 H 0.3260(10) 0.1405(8) 0.5999(2) 0.0264(19) Uiso 1.000000 R F2 F 0.8552(9) 0.2328(8) 0.2971(2) 0.0339(15) Uani 1.000000 . C6 C 0.3701(10) 0.6267(8) 0.5907(2) 0.0222(16) Uani 1.000000 . H6 H 0.4230(10) 0.7407(8) 0.5642(2) 0.0266(19) Uiso 1.000000 R O2 O 0.2563(9) 0.8476(7) 0.65970(18) 0.0258(14) Uani 1.000000 . N1 N 0.4484(9) 0.2160(7) 0.50478(17) 0.0228(14) Uani 1.000000 . H1 H 0.3476(9) 0.1314(7) 0.52272(17) 0.0273(16) Uiso 1.000000 R O3 O 0.1468(10) 0.6153(8) 0.71644(19) 0.0324(16) Uani 1.000000 . C9 C 0.5308(9) 0.1413(7) 0.45769(19) 0.0162(15) Uani 1.000000 . C15 C 0.7031(11) 0.2959(8) 0.3225(2) 0.0245(19) Uani 1.000000 . C7 C 0.2853(10) 0.6729(8) 0.6383(2) 0.0177(15) Uani 1.000000 . C10 C 0.5883(11) 0.2574(8) 0.4163(2) 0.0243(13) Uani 1.000000 . H10 H 0.5761(11) 0.4158(8) 0.4192(2) 0.0292(15) Uiso 1.000000 R C2 C 0.2196(10) 0.5333(8) 0.6722(2) 0.0214(17) Uani 1.000000 . C5 C 0.3868(10) 0.4333(8) 0.5773(2) 0.0192(12) Uani 1.000000 . C13 C 0.6259(11) -0.1394(8) 0.4086(2) 0.0247(17) Uani 1.000000 . H13 H 0.6421(11) -0.2976(8) 0.4066(2) 0.030(2) Uiso 1.000000 R C3 C 0.2321(11) 0.3394(8) 0.6600(2) 0.0254(17) Uani 1.000000 . H3 H 0.1791(11) 0.2269(8) 0.6869(2) 0.030(2) Uiso 1.000000 R C11 C 0.6625(11) 0.1724(8) 0.3703(2) 0.0243(13) Uani 1.000000 . C12 C 0.6837(11) -0.0242(8) 0.3660(2) 0.0221(16) Uani 1.000000 . H12 H 0.7445(11) -0.0892(8) 0.3300(2) 0.0266(19) Uiso 1.000000 R C14 C 0.5479(10) -0.0555(8) 0.4538(2) 0.0206(15) Uani 1.000000 . H14 H 0.4994(10) -0.1482(8) 0.4867(2) 0.0247(18) Uiso 1.000000 R C1 C 0.1880(11) 0.8122(8) 0.7124(2) 0.0277(18) Uani 1.000000 . H1a H 0.2942(11) 0.8532(8) 0.7439(2) 0.033(2) Uiso 1.000000 R H1b H 0.0617(11) 0.8997(8) 0.7187(2) 0.033(2) Uiso 1.000000 R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C8 0.023(3) 0.0216(19) 0.0136(18) -0.0052(18) 0.0097(19) -0.0038(13) F3 0.057(5) 0.039(3) 0.013(2) -0.003(3) 0.007(2) 0.0036(17) O1 0.051(4) 0.020(2) 0.018(2) -0.019(2) 0.019(2) -0.0090(15) F1 0.052(4) 0.021(2) 0.022(2) -0.011(2) 0.023(2) -0.0005(15) C4 0.033(5) 0.014(3) 0.020(3) 0.006(2) 0.019(3) -0.0008(19) F2 0.043(4) 0.035(2) 0.025(2) 0.008(2) 0.022(2) -0.0012(18) C6 0.033(5) 0.020(3) 0.015(2) -0.006(3) 0.012(3) -0.0022(19) O2 0.039(5) 0.017(2) 0.021(2) 0.006(2) 0.006(2) 0.0019(15) N1 0.041(4) 0.022(2) 0.006(2) -0.002(2) 0.009(2) -0.0003(16) O3 0.053(5) 0.031(3) 0.015(2) 0.011(3) 0.020(2) -0.0010(18) C9 0.029(5) 0.010(2) 0.010(2) -0.004(2) 0.007(3) 0.0010(17) C15 0.046(6) 0.020(3) 0.009(2) 0.000(3) 0.011(3) 0.0038(18) C7 0.023(5) 0.017(3) 0.013(2) -0.004(2) 0.004(3) -0.0024(18) C10 0.046(4) 0.0175(18) 0.0107(17) 0.0001(18) 0.015(2) -0.0017(13) C2 0.028(5) 0.024(3) 0.014(2) 0.007(3) 0.014(3) 0.000(2) C5 0.023(3) 0.0216(19) 0.0136(18) -0.0052(18) 0.0097(19) -0.0038(13) C13 0.045(6) 0.013(3) 0.017(3) 0.003(3) 0.014(3) -0.0013(19) C3 0.047(6) 0.017(3) 0.012(2) -0.004(3) 0.014(3) -0.0004(19) C11 0.046(4) 0.0175(18) 0.0107(17) 0.0001(18) 0.015(2) -0.0017(13) C12 0.029(5) 0.021(3) 0.017(3) -0.003(3) 0.010(3) -0.002(2) C14 0.036(5) 0.014(2) 0.012(2) -0.003(2) 0.011(3) -0.0022(18) C1 0.043(6) 0.022(3) 0.018(3) 0.004(3) 0.010(3) -0.001(2) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_dispersion_source C 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom F 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom N 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom O 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom loop_ _diffrn_refln_index_h _diffrn_refln_index_k _diffrn_refln_index_l _diffrn_refln_intensity_net _diffrn_refln_intensity_u 0 0 -4 4011.63 538.3 0 0 4 2535.09 341.02 0 0 -6 2474.94 334.46 0 0 6 3753.01 505.21 0 0 -8 1067.56 148.36 0 0 8 1775.76 242.69 0 0 -10 4251.71 574.38 0 0 10 4386.03 592.42 0 0 -12 977.34 139.49 0 0 12 838.01 121.64 0 0 -14 8069.37 1086.61 0 0 14 7387.73 995.39 0 0 -16 3669.81 501.2 0 0 16 4063.26 553.33 0 0 -18 2152.17 300.62 0 0 18 1635.43 230.96 0 0 -20 2820.77 390.99 0 0 20 2530.07 351.4 0 0 -22 1292.6 190.26 0 0 22 1171.81 173.71 0 0 -24 2485.96 348.84 0 0 24 2356.16 331.85 0 0 -26 764.83 123.05 0 0 26 641.04 108.81 0 0 -28 214.37 58.44 0 0 28 168.85 58.44 0 0 -30 16.22 38.63 0 0 30 10.19 43.62 0 0 -32 -15.73 44.24 0 0 32 1.73 51.67 0 0 -34 32.99 47.12 0 0 34 47.6 64.76 0 2 -2 2722.53 368.38 0 -2 2 2312.55 313.3 0 2 3 864.57 117.98 0 -2 -3 867.58 118.03 0 2 -3 876.1 121.14 0 -2 3 829.99 115.13 0 2 4 130.17 21.41 0 2 -4 85.3 19.31 0 -2 4 114.83 22.16 0 -2 -5 559.84 77.69 0 2 -5 654.07 92.57 0 -2 5 711.21 100.59 0 2 6 3937.95 528.27 0 -2 -6 4500.3 603.95 0 2 -6 4227.65 569.86 0 -2 6 4203.59 566.86 0 2 7 1436.95 195.42 0 -2 -7 1381.81 187.95 0 2 -7 1385.82 191.11 0 -2 7 1337.21 184.94 0 2 8 3343.03 450.39 0 -2 -8 2685.44 362.67 0 2 -8 3798.61 515.24 0 -2 8 3117.48 423.12 0 2 9 5387.94 723.74 0 -2 -9 4867.18 654.07 0 2 -9 4296.81 580.39 0 -2 9 5648.56 762.33 0 2 10 4856.66 653.57 0 -2 -10 4613.07 620.99 0 2 -10 4927.83 665.59 0 -2 10 4399.56 595.43 0 2 11 772.85 109.51 0 -2 -11 842.02 118.59 0 2 -11 1042.51 148.76 0 -2 11 746.3 109.71 0 2 12 2756.62 374.25 0 -2 -12 2227.85 303.88 0 2 -12 2601.74 356.3 0 -2 12 2390.74 329.59 0 2 13 435.65 66.81 0 -2 -13 635.03 93.32 0 2 -13 676.62 101.74 0 -2 13 674.62 102.45 0 2 14 800.42 115.73 0 -2 -14 883.12 127.11 0 2 -14 763.83 114.23 0 -2 14 606.96 94.88 0 2 15 1645.95 228.35 0 -2 -15 1673.01 232.76 0 2 -15 1984.26 276.41 0 -2 15 2038.39 284.78 0 2 16 1271.05 179.93 0 -2 -16 1160.29 165.09 0 2 -16 1055.54 154.12 0 -2 16 1109.16 162.29 0 2 17 126.71 35 0 -2 -17 67.81 28.53 0 2 -17 75.38 33.17 0 -2 17 100.04 34.35 0 2 18 335.66 59.54 0 -2 -18 334.51 60.24 0 2 -18 288.49 57.04 0 -2 18 387.18 70.22 0 2 19 260.47 49.4 0 -2 -19 161.68 40.82 0 2 -19 237.42 52.88 0 -2 19 103.65 39.81 0 2 20 435.75 72.62 0 -2 -20 266.03 53.43 0 2 -20 253.05 57.74 0 -2 20 340.47 69.32 0 2 21 1159.79 168.15 0 -2 -21 1032.48 152.36 0 2 -21 1124.7 169.2 0 -2 21 1110.16 168.8 0 2 22 390.74 69.42 0 -2 -22 294.41 59.59 0 2 -22 213.21 54.63 0 -2 22 335.86 71.77 0 2 23 1718.63 243.74 0 -2 -23 1328.69 192.01 0 2 -23 1827.39 262.43 0 -2 23 1528.67 225.39 0 2 24 106.56 39.02 0 -2 -24 177.67 46.94 0 2 -24 127.61 49.3 0 -2 24 211.21 59.74 0 2 25 804.93 125.9 0 -2 -25 879.11 134.28 0 2 -25 708.7 116.23 0 -2 25 1231.96 188.65 0 2 26 95.43 42.6 0 -2 -26 32.76 32.16 0 2 -26 40.79 43.04 0 -2 26 32.68 44.31 0 2 27 164.84 49.97 0 -2 -27 121.64 43.6 0 2 -27 120.24 48.57 0 -2 27 269.54 72.93 0 2 28 78.44 44.69 0 -2 -28 198.93 51.17 0 2 -28 92.07 47.84 0 -2 28 145 59.79 0 2 29 109.86 48.92 0 -2 -29 112.02 44.49 0 2 -29 83.05 45.5 0 -2 29 98.09 57.99 0 2 30 80.89 45.67 0 -2 -30 108.36 45.56 0 2 -30 18.49 43.03 0 -2 30 49.12 53.43 0 2 31 31.02 48.86 0 -2 -31 35 37.09 0 2 -31 27.28 51.02 0 -2 31 -11.05 52.48 0 2 32 119.09 56.44 0 -2 -32 122.85 51.17 0 2 -32 186.04 71.92 0 -2 32 71.87 65.56 0 2 33 12.87 48.51 0 -2 -33 16.55 42.9 0 2 -33 -14.72 55.88 0 -2 33 -9.42 60.55 0 4 -2 797.91 122.65 0 -4 2 1123.7 159.33 0 4 -3 1630.92 231.91 0 -4 3 1585.3 221.03 0 4 -4 1417.9 200.33 0 -4 4 1650.97 229.3 0 4 5 895.65 127.61 0 -4 -5 1219.43 167.2 0 4 -5 1467.02 204.39 0 -4 5 1560.75 217.12 0 4 6 1088.61 150.22 0 -4 -6 1328.19 181.73 0 4 -6 1002.91 142.75 0 -4 6 1214.42 171.06 0 4 7 798.42 110.82 0 -4 -7 954.29 131.67 0 4 -7 1110.67 158.93 0 -4 7 792.4 115.83 0 4 8 130.62 25.33 0 4 -8 167.3 37.11 0 -4 8 95.53 26.61 0 4 9 611.97 87.11 0 -4 -9 629.01 88.81 0 4 -9 605.45 92.62 0 -4 9 670.1 101.24 0 4 10 506.72 73.93 0 -4 -10 689.15 96.88 0 4 -10 744.79 110.87 0 -4 10 562.85 87.71 0 4 11 564.85 82.5 0 -4 -11 565.85 81.09 0 4 -11 580.89 89.82 0 -4 11 641.54 98.74 0 4 12 873.59 123.3 0 -4 -12 741.78 105.05 0 4 -12 882.11 130.57 0 -4 12 722.74 110.32 0 4 13 233.11 41.39 0 -4 -13 132.72 28.12 0 4 -13 199.08 46.39 0 -4 13 175.12 41.39 0 4 14 728.75 105.65 0 -4 -14 583.4 85.71 0 4 -14 695.17 109.01 0 -4 14 519.25 86.51 0 4 15 2192.26 300.27 0 -4 -15 1959.71 268.94 0 4 -15 2040.9 288.24 0 -4 15 1997.79 282.88 0 4 16 1970.73 271.4 0 -4 -16 2438.86 333.45 0 4 -16 2631.32 367.53 0 -4 16 2437.85 342.13 0 4 17 1367.28 192.11 0 -4 -17 1058.04 150.72 0 4 -17 1306.13 193.11 0 -4 17 1307.64 194.27 0 4 18 826.49 121.29 0 4 -18 551.83 94.88 0 -4 18 917.7 142.4 0 4 19 640.04 97.28 0 -4 -19 846.03 125.35 0 4 -19 524.76 93.52 0 -4 19 515.74 92.62 0 4 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49.29 7 3 -13 37.74 39.26 -7 -3 13 38.17 41.98 -7 3 13 29.61 81.25 7 -3 -13 31.11 46.3 7 3 -12 91.07 47.35 -7 -3 12 233.96 57.59 -7 3 12 72.17 91.32 7 -3 -12 383.47 86.61 7 3 -11 47.1 39.23 -7 -3 11 78.29 42.2 -7 3 11 5.28 78.79 7 -3 -11 101.54 56.13 7 3 -10 118.14 46.75 -7 -3 10 169.25 49.67 -7 3 10 1.27 81.7 7 -3 -10 124.45 56.34 7 3 -9 140.74 49.49 -7 -3 9 123.55 45.44 7 3 -8 12.88 42.08 -7 -3 8 46.07 37.37 7 3 -7 85.05 53.58 -7 -3 7 144.45 51.02 7 3 -6 229.5 69.47 -7 -3 6 165.79 55.43 7 3 -4 74.43 51.02 -7 -3 4 87.11 42.1 7 3 -3 31.48 42.16 -7 -3 3 19.02 36.16 7 -5 -18 21.37 44.86 7 5 -17 84.8 48.21 -7 -5 17 35.25 40.41 -7 5 17 9.15 72.47 7 -5 -17 5.22 42.11 7 5 -16 20.2 41.1 -7 -5 16 40.74 37.27 -7 5 16 47.8 75.73 7 -5 -16 5.41 41.3 7 5 -15 -16.26 39.09 -7 -5 15 14.2 35.71 -7 5 15 0.18 68.56 7 -5 -15 -0.69 41.43 7 5 -14 10.84 37.99 -7 -5 14 35.28 34.52 -7 5 14 -3.59 74.53 7 -5 -14 15.89 41.59 7 5 -13 48.86 41.44 -7 -5 13 98.74 40.85 -7 5 13 -22.2 73.08 7 -5 -13 168.25 56.08 7 5 -12 16.93 40.52 -7 -5 12 50.82 35.37 -7 5 12 -12.55 69.72 7 5 -11 20.51 41.22 -7 -5 11 105.3 39.51 -7 -5 10 42.87 35.3 7 5 -9 252.7 58.99 -7 -5 9 92.17 40.64 7 5 -8 90.47 42.34 -7 -5 8 87.91 36.18 7 5 -7 87.96 40.24 -7 -5 7 55.88 33.92 7 5 -6 4.41 33.6 -7 -5 6 7.05 26.28 7 5 -5 76.63 46.06 -7 -5 5 45.07 29.42 7 5 -4 355.6 74.88 -7 -5 4 369.83 66.71 7 5 -3 312.65 68.61 -7 -5 3 487.37 81.4 7 5 -2 192.66 54.93 -7 -5 2 33.29 29.72 7 5 -1 27.28 39.32 -7 -5 1 57.09 29.48 -7 -5 0 16.11 26.03 -8 0 20 -8.72 56.54 8 0 -20 55.68 50.72 -8 0 18 64.86 57.44 8 0 -18 142.9 56.94 -8 0 16 33.92 50.87 8 0 -16 38.24 48.83 -8 0 14 10.95 51.07 8 0 -14 11.22 46.31 -8 0 12 167.95 73.63 8 0 -12 238.53 73.63 -8 0 10 200.08 75.78 8 0 -10 190.86 64.91 -8 0 8 280.72 84.55 8 0 -8 581.89 109.96 8 2 -20 -2.62 51.32 -8 -2 20 14.7 50.27 -8 2 20 -9.24 52.33 8 -2 -20 4.21 46.27 8 2 -19 23.44 47.22 -8 -2 19 19.27 51.32 -8 2 19 45.48 58.14 8 -2 -19 159.18 58.54 8 2 -18 194.57 65.06 -8 -2 18 63.1 52.68 -8 2 18 5.01 60.24 8 -2 -18 41.85 50.87 8 2 -17 12.13 46.97 -8 -2 17 20.39 51.27 -8 2 17 20.25 62.8 8 -2 -17 -8.85 46.77 8 2 -16 57.04 48.64 -8 -2 16 61.3 44.72 -8 2 16 21.28 69.57 8 -2 -16 78.64 59.89 8 2 -15 34.97 45.56 -8 -2 15 24.96 44.31 -8 2 15 -5.64 77.39 8 -2 -15 56.64 54.88 8 2 -14 24.33 45.5 -8 -2 14 55.58 44.66 -8 2 14 42.28 81.5 8 -2 -14 49.75 52.58 8 2 -13 262.48 69.57 -8 -2 13 55.18 44.08 -8 2 13 36.29 78.49 8 -2 -13 106.71 59.79 8 2 -12 29.19 47.38 -8 -2 12 19.82 41.51 -8 2 12 49.52 76.53 8 -2 -12 127.96 59.89 8 2 -11 128.21 57.64 -8 -2 11 166.55 58.34 -8 2 11 -9 69.12 8 -2 -11 112.37 58.99 8 2 -10 140.29 60.85 -8 -2 10 84.15 51.22 -8 2 10 29.33 73.03 8 -2 -10 96.38 58.14 8 2 -9 136.18 59.04 -8 -2 9 214.82 64.96 -8 2 9 -40.21 64.86 8 2 -8 32.78 48.72 -8 -2 8 42.67 48.93 8 2 -7 314.46 75.08 -8 -2 7 356.45 78.89 8 2 -6 88.11 51.12 -8 -2 6 62.35 48.38 8 2 -5 15.06 41.91 -8 -2 5 8.55 41.82 8 4 -16 25.46 55.53 -8 -4 16 45.53 47.13 -8 4 16 -13.64 82.65 8 -4 -16 40.42 47.01 8 4 -15 44.74 49.47 -8 -4 15 -8.11 40.23 -8 4 15 9.75 79.19 8 -4 -15 -1.95 41.38 8 4 -14 13.48 38.1 -8 -4 14 9.94 39.28 -8 4 14 33.65 77.99 8 -4 -14 21.32 44.05 8 4 -13 -13.15 38.16 -8 -4 13 5.99 39.61 -8 4 13 -9.07 77.19 8 -4 -13 7.52 42.71 8 4 -12 22.41 38.67 -8 -4 12 -14.23 35.22 -8 4 12 -20.83 76.48 8 4 -11 16.11 38.11 -8 -4 11 18.46 36.79 -8 4 11 0.83 66.71 8 4 -10 69.67 47.27 -8 -4 10 22.65 36.91 8 4 -9 46.23 46.75 -8 -4 9 8.5 32.93 8 4 -8 8.23 43.87 -8 -4 8 56.08 37.52 8 4 -7 113.22 54.73 -8 -4 7 135.73 45.64 8 4 -6 60.7 49.09 -8 -4 6 76.43 40.14 8 4 -5 70.52 49.94 -8 -4 5 90.12 41.15 8 4 -4 59.39 45.91 -8 -4 4 43.42 34.55 8 4 -3 195.67 58.14 -8 -4 3 76.53 38.15 -8 -4 2 14.41 30.17 9 1 -16 22.4 50.97 9 -1 -16 104.2 62.45 9 1 -15 11.28 47.11 -9 -1 15 13.84 46.3 -9 1 15 -0.75 61.9 9 -1 -15 35.86 55.58 9 1 -14 27.63 49.58 -9 -1 14 1.05 50.57 -9 1 14 16.15 66.36 9 -1 -14 30.41 52.02 9 1 -13 16.79 49.33 -9 -1 13 21.54 51.77 -9 1 13 -8.91 61.4 9 -1 -13 45.19 51.52 9 1 -12 6.4 50.57 -9 -1 12 40.47 57.89 -9 1 12 -4.27 58.34 9 -1 -12 52.43 52.08 9 1 -11 77.49 56.23 -9 -1 11 29.92 59.39 -9 1 11 -13.3 58.54 9 -1 -11 18.86 47.61 9 1 -10 133.42 59.89 -9 -1 10 -24.24 53.73 -9 1 10 2.68 57.84 9 -1 -10 45.64 49.33 9 1 -9 144.25 62.8 -9 -1 9 37.46 59.49 -9 1 9 -12.42 65.01 9 1 -8 94.58 55.33 -9 -1 8 -0.32 48.35 -9 -1 7 17.66 44.76 -9 -1 6 -11.55 45.53 -9 3 12 3.4 79.59 9 -3 -12 24.25 49.72 9 3 -11 3.45 47.55 -9 -3 11 0.13 39.33 -9 3 11 -18.18 68.01 9 3 -10 64.81 50.97 -9 -3 10 -0.13 38.7 9 3 -9 -9.33 46.36 -9 -3 9 9.17 39.68 9 3 -8 59.79 54.23 -9 -3 8 42.29 45.38 9 3 -7 101.44 55.23 -9 -3 7 -0.08 38.17 9 3 -6 43.32 46.67 -9 -3 6 20.21 38.66 9 3 -5 9.29 41.62 -9 -3 5 -3.74 38.71 -9 -3 4 9.85 36.72 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 N1 C8 O1 123.8(5) . . C5 C8 O1 119.6(5) . . C5 C8 N1 116.5(5) . . C5 C4 H4 118.5(3) . . C3 C4 H4 118.5(3) . . C3 C4 C5 122.9(5) . . C7 C6 H6 120.9(3) . . C5 C6 H6 120.9(3) . . C5 C6 C7 118.1(5) . . C1 O2 C7 105.6(4) . . H1 N1 C8 117.4(3) . . C9 N1 C8 125.1(5) . . C9 N1 H1 117.4(3) . . C1 O3 C2 105.2(5) . . C10 C9 N1 122.8(5) . . C14 C9 N1 117.4(4) . . C14 C9 C10 119.8(4) . . F1 C15 F3 107.4(6) . . F2 C15 F3 106.9(5) . . F2 C15 F1 105.4(6) . . C11 C15 F3 113.1(6) . . C11 C15 F1 112.2(5) . . C11 C15 F2 111.4(6) . . O2 C7 C6 128.6(5) . . C2 C7 C6 121.9(5) . . C2 C7 O2 109.4(5) . . H10 C10 C9 120.3(3) . . C11 C10 C9 119.4(5) . . C11 C10 H10 120.3(3) . . C7 C2 O3 110.4(5) . . C3 C2 O3 128.0(5) . . C3 C2 C7 121.6(5) . . C4 C5 C8 122.7(5) . . C6 C5 C8 118.1(5) . . C6 C5 C4 119.2(5) . . C12 C13 H13 119.8(3) . . C14 C13 H13 119.8(3) . . C14 C13 C12 120.4(5) . . C2 C3 C4 116.2(5) . . H3 C3 C4 121.9(3) . . H3 C3 C2 121.9(3) . . C10 C11 C15 119.4(5) . . C12 C11 C15 118.8(4) . . C12 C11 C10 121.6(5) . . C11 C12 C13 118.1(5) . . H12 C12 C13 120.9(3) . . H12 C12 C11 120.9(3) . . C13 C14 C9 120.7(4) . . H14 C14 C9 119.7(3) . . H14 C14 C13 119.7(3) . . O3 C1 O2 108.2(4) . . H1a C1 O2 110.1(4) . . H1a C1 O3 110.1(4) . . H1b C1 O2 110.1(3) . . H1b C1 O3 110.1(4) . . H1b C1 H1a 108.4 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C8 O1 1.219(7) . C8 N1 1.292(7) . C8 C5 1.473(7) . F3 C15 1.309(9) . F1 C15 1.289(7) . C4 H4 1.0830 . C4 C5 1.370(7) . C4 C3 1.370(7) . F2 C15 1.332(8) . C6 H6 1.0830 . C6 C7 1.358(7) . C6 C5 1.361(7) . O2 C7 1.316(6) . O2 C1 1.406(7) . N1 H1 1.0270 . N1 C9 1.398(6) . O3 C2 1.331(6) . O3 C1 1.375(8) . C9 C10 1.353(7) . C9 C14 1.347(7) . C15 C11 1.469(7) . C7 C2 1.350(7) . C10 H10 1.0830 . C10 C11 1.379(7) . C2 C3 1.355(7) . C13 H13 1.0830 . C13 C12 1.371(7) . C13 C14 1.370(7) . C3 H3 1.0830 . C11 C12 1.350(7) . C12 H12 1.0830 . C14 H14 1.0830 . C1 H1a 1.0910 . C1 H1b 1.0910 . 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 C8 N1 C9 C10 -33.1(8) . . . . C8 N1 C9 C14 148.6(7) . . . . C8 C5 C4 C3 175.3(7) . . . . C8 C5 C6 C7 -176.3(6) . . . . F3 C15 C11 C10 -94.0(6) . . . . F3 C15 C11 C12 80.3(7) . . . . F1 C15 C11 C10 27.7(8) . . . . F1 C15 C11 C12 -158.0(7) . . . . C4 C5 C6 C7 0.9(9) . . . . C4 C3 C2 O3 -179.4(7) . . . . C4 C3 C2 C7 0.3(9) . . . . F2 C15 C11 C10 145.5(6) . . . . F2 C15 C11 C12 -40.2(8) . . . . C6 C7 O2 C1 -171.9(8) . . . . C6 C7 C2 O3 178.6(7) . . . . C6 C7 C2 C3 -1.1(9) . . . . O2 C7 C2 O3 -0.1(7) . . . . O2 C7 C2 C3 -179.9(6) . . . . O2 C1 O3 C2 10.6(6) . . . . N1 C9 C10 C11 -177.8(8) . . . . N1 C9 C14 C13 179.5(6) . . . . C9 C10 C11 C15 172.5(7) . . . . C9 C10 C11 C12 -1.6(9) . . . . C9 C14 C13 C12 -1.6(9) . . . . C15 C11 C12 C13 -173.0(7) . . . . C10 C11 C12 C13 1.2(9) . . . . loop_ _audit_support.id _audit_support.funding_organization _audit_support.funding_organization_doi _audit_support.funding_organization_url _audit_support.award_type _audit_support.award_number _audit_support.award_recipient 1 'Narodowe Centrum Nauki' https://doi.org/10.13039/501100004281 https://ror.org/03ha2q922 grant 2020/39/I/ST4/02904 'P. M. Dominiak'