#------------------------------------------------------------------------------ #$Date: 2021-09-04 15:42:56 +0300 (Sat, 04 Sep 2021) $ #$Revision: 268481 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128939.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_7128939 loop_ _publ_author_name 'Vygranenko, Kateryna V.' 'Poronik, Yevgen M.' 'Wrzosek, Antoni' 'Szewczyk, Adam' 'Gryko, Daniel T.' _publ_section_title ; Red emissive sulfone-rhodols as mitochondrial imaging agents. ; _journal_issue 63 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 7782 _journal_page_last 7785 _journal_paper_doi 10.1039/d1cc02687a _journal_volume 57 _journal_year 2021 _chemical_formula_moiety 'C23 H18 F3 N O4 S' _chemical_formula_sum 'C23 H18 F3 N O4 S' _chemical_formula_weight 461.44 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014 _audit_update_record ; 2021-05-19 deposited with the CCDC. 2021-07-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.394(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 20.3851(10) _cell_length_b 12.4673(5) _cell_length_c 8.0484(4) _cell_measurement_reflns_used 1758 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 66.56 _cell_measurement_theta_min 4.16 _cell_volume 2043.69(16) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.965 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.1400 _diffrn_reflns_av_unetI/netI 0.0917 _diffrn_reflns_Laue_measured_fraction_full 0.965 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 23160 _diffrn_reflns_point_group_measured_fraction_full 0.965 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 66.564 _diffrn_reflns_theta_min 4.157 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.944 _exptl_absorpt_correction_T_max 0.8030 _exptl_absorpt_correction_T_min 0.6410 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details sadabs _exptl_crystal_colour violet-brown _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.251 _exptl_crystal_size_mid 0.245 _exptl_crystal_size_min 0.118 _refine_diff_density_max 0.360 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 292 _refine_ls_number_reflns 3564 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.1516 _refine_ls_R_factor_gt 0.0673 _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^)+(0.0650P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1486 _refine_ls_wR_factor_ref 0.1728 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1758 _reflns_number_total 3564 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc02687a2.cif _cod_data_source_block KVy0363_10_A_0ma _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7128939 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.641 _shelx_estimated_absorpt_t_max 0.803 _shelxl_version_number 2014-3 _shelx_res_file ; TITL KVy0363_10_A_0ma in P2(1)/c CELL 1.54178 20.38510 12.46730 8.04840 90.0000 92.3943 90.0000 ZERR 4.00 0.00100 0.00050 0.00040 0.0000 0.0033 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O F S UNIT 92 72 4 16 12 4 MERG 2 OMIT 0 L.S. 30 ACTA BOND $H FMAP 2 PLAN 4 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 HTAB C22 O2_$4 HTAB C22 O1_$3 HTAB C18 F3_$2 HTAB C10 F2_$1 HTAB C22 O3_$5 EQIV $5 x, y+1, z HTAB C22 O2_$4 EQIV $4 x, -y+3/2, z-1/2 HTAB C22 O1_$3 EQIV $3 x, -y+3/2, z+1/2 HTAB C18 F3_$2 EQIV $2 x, y, z+1 HTAB C10 F2_$1 EQIV $1 x, -y+1/2, z+1/2 HTAB CONF SIZE 0.118 0.245 0.251 HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 TEMP 23.000 WGHT 0.065000 FVAR 0.09656 MOLE 1 S1 6 0.619292 0.430470 0.577750 11.00000 0.05412 0.04466 = 0.09216 -0.00512 -0.00909 -0.00303 F1 5 0.826842 0.581337 0.424585 11.00000 0.09443 0.36161 = 0.05706 0.00050 -0.01482 0.03929 F2 5 0.884480 0.448490 0.473901 11.00000 0.26993 0.13393 = 0.10171 -0.05070 0.01951 -0.04432 F3 5 0.928824 0.590415 0.435532 11.00000 0.10932 0.21547 = 0.06899 -0.02032 0.01331 -0.07135 O1 4 0.596139 0.408131 0.411983 11.00000 0.13188 0.05862 = 0.10411 -0.01165 -0.05830 -0.00178 O2 4 0.573382 0.414369 0.705601 11.00000 0.06497 0.06085 = 0.14693 -0.00298 0.04373 -0.00769 O3 4 0.723791 0.071741 0.644425 11.00000 0.07801 0.04687 = 0.20491 -0.01254 0.00690 0.00206 O4 4 0.993329 0.670876 1.017551 11.00000 0.07134 0.11297 = 0.07039 -0.00756 -0.01763 -0.01664 N1 3 0.575119 0.826398 0.513786 11.00000 0.05663 0.04320 = 0.10554 -0.00958 -0.01346 0.00020 C1 1 0.648176 0.562873 0.593342 11.00000 0.04700 0.04804 = 0.06969 -0.00249 -0.00441 -0.00347 C2 1 0.603526 0.639423 0.545253 11.00000 0.04679 0.04624 = 0.08450 -0.00447 -0.00951 -0.00112 AFIX 43 H2 2 0.562773 0.618740 0.499832 11.00000 -1.20000 AFIX 0 C3 1 0.618308 0.750393 0.563475 11.00000 0.05024 0.04349 = 0.08222 -0.00039 -0.00085 0.00369 C4 1 0.680061 0.775456 0.637350 11.00000 0.05263 0.04391 = 0.08758 -0.00398 -0.00331 -0.00464 AFIX 43 H4 2 0.690873 0.846958 0.656821 11.00000 -1.20000 AFIX 0 C5 1 0.724437 0.698057 0.681144 11.00000 0.04723 0.05111 = 0.08424 -0.00138 -0.01057 -0.00800 AFIX 43 H5 2 0.765298 0.718713 0.725918 11.00000 -1.20000 AFIX 0 C6 1 0.711019 0.587377 0.661411 11.00000 0.05384 0.04143 = 0.06467 0.00532 -0.00256 -0.00224 C7 1 0.759455 0.507406 0.707230 11.00000 0.05296 0.05011 = 0.05677 -0.00029 -0.01011 -0.00635 C8 1 0.748542 0.397872 0.692619 11.00000 0.04759 0.05487 = 0.06796 0.00439 -0.00206 -0.00238 C9 1 0.798278 0.322406 0.743161 11.00000 0.06274 0.05903 = 0.08197 0.00717 -0.01388 0.00397 AFIX 43 H9 2 0.837948 0.348452 0.787931 11.00000 -1.20000 AFIX 0 C10 1 0.790539 0.215715 0.729177 11.00000 0.06105 0.05799 = 0.09701 0.01282 -0.00419 0.00845 AFIX 43 H10 2 0.824761 0.170902 0.764949 11.00000 -1.20000 AFIX 0 C11 1 0.731522 0.169177 0.661239 11.00000 0.06862 0.04913 = 0.10471 0.00164 0.01341 0.00418 C12 1 0.679776 0.244964 0.609891 11.00000 0.05609 0.04808 = 0.11441 -0.00763 0.00327 -0.00213 AFIX 43 H12 2 0.640291 0.219224 0.563544 11.00000 -1.20000 AFIX 0 C13 1 0.688399 0.351096 0.628635 11.00000 0.05166 0.04423 = 0.07229 -0.00205 0.00286 -0.00433 C14 1 0.823602 0.547944 0.781475 11.00000 0.05420 0.04748 = 0.05338 0.00079 -0.00395 -0.00186 C15 1 0.878505 0.569964 0.691094 11.00000 0.06173 0.05811 = 0.04846 -0.00580 -0.00355 -0.00569 C16 1 0.935620 0.609591 0.765160 11.00000 0.05557 0.07908 = 0.05092 -0.00607 -0.00161 -0.00745 AFIX 43 H16 2 0.971818 0.622701 0.701549 11.00000 -1.20000 AFIX 0 C17 1 0.939000 0.629423 0.930594 11.00000 0.05696 0.06787 = 0.05591 0.00007 -0.00591 -0.01069 C18 1 0.885767 0.608865 1.024063 11.00000 0.08039 0.08406 = 0.04916 -0.00469 -0.00555 -0.01083 AFIX 43 H18 2 0.887961 0.622842 1.137664 11.00000 -1.20000 AFIX 0 C19 1 0.829217 0.567724 0.950689 11.00000 0.06332 0.06999 = 0.06761 -0.00100 0.00210 -0.01213 AFIX 43 H19 2 0.793835 0.552785 1.016223 11.00000 -1.20000 AFIX 0 C20 1 0.878441 0.550622 0.509275 11.00000 0.07098 0.08836 = 0.07344 -0.01114 0.00149 -0.02490 C21 1 1.047783 0.696192 0.923808 11.00000 0.06272 0.12617 = 0.10770 -0.00540 -0.01121 -0.02251 AFIX 137 H21A 2 1.065398 0.631648 0.878304 11.00000 -1.50000 H21B 2 1.080754 0.730416 0.994042 11.00000 -1.50000 H21C 2 1.034430 0.743823 0.834979 11.00000 -1.50000 AFIX 0 C22 1 0.588419 0.938453 0.549273 11.00000 0.07966 0.04363 = 0.14798 -0.00516 -0.02195 0.00223 AFIX 137 H22A 2 0.582263 0.952288 0.664920 11.00000 -1.50000 H22B 2 0.558924 0.982449 0.482816 11.00000 -1.50000 H22C 2 0.632879 0.954847 0.523589 11.00000 -1.50000 AFIX 0 C23 1 0.512734 0.801046 0.433725 11.00000 0.07250 0.06331 = 0.11408 -0.00827 -0.02124 0.00430 AFIX 137 H23A 2 0.518078 0.743424 0.356333 11.00000 -1.50000 H23B 2 0.495920 0.863045 0.375436 11.00000 -1.50000 H23C 2 0.482517 0.779728 0.515906 11.00000 -1.50000 AFIX 0 HKLF 4 REM KVy0363_10_A_0ma in P2(1)/c REM R1 = 0.0673 for 1758 Fo > 4sig(Fo) and 0.1516 for all 3564 data REM 292 parameters refined using 0 restraints END WGHT 0.0747 0.0000 REM Instructions for potential hydrogen bonds HTAB C10 F2_$1 HTAB C18 F3_$2 HTAB C22 O1_$3 HTAB C22 O2_$4 HTAB C22 O3_$5 REM Highest difference peak 0.360, deepest hole -0.260, 1-sigma level 0.051 Q1 1 0.8619 0.6517 0.4418 11.00000 0.05 0.36 Q2 1 0.8365 0.5111 0.4357 11.00000 0.05 0.28 Q3 1 0.5808 0.3335 0.4805 11.00000 0.05 0.21 Q4 1 0.6128 0.7020 0.5357 11.00000 0.05 0.20 ; _shelx_res_checksum 87865 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_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 S1 S 0.61929(6) 0.43047(9) 0.57775(18) 0.0640(4) Uani 1 1 d . . . . . F1 F 0.82684(18) 0.5813(4) 0.4246(4) 0.172(2) Uani 1 1 d . . . . . F2 F 0.8845(3) 0.4485(3) 0.4739(5) 0.168(2) Uani 1 1 d . . . . . F3 F 0.92882(17) 0.5904(3) 0.4355(4) 0.1310(15) Uani 1 1 d . . . . . O1 O 0.59614(18) 0.4081(2) 0.4120(5) 0.1000(13) Uani 1 1 d . . . . . O2 O 0.57338(16) 0.4144(2) 0.7056(5) 0.0898(12) Uani 1 1 d . . . . . O3 O 0.72379(17) 0.0717(3) 0.6444(5) 0.1099(15) Uani 1 1 d . . . . . O4 O 0.99333(17) 0.6709(3) 1.0176(4) 0.0855(11) Uani 1 1 d . . . . . N1 N 0.57512(17) 0.8264(3) 0.5138(5) 0.0689(12) Uani 1 1 d . . . . . C1 C 0.6482(2) 0.5629(3) 0.5933(6) 0.0551(12) Uani 1 1 d . . . . . C2 C 0.6035(2) 0.6394(3) 0.5453(6) 0.0595(13) Uani 1 1 d . . . . . H2 H 0.5628 0.6187 0.4998 0.071 Uiso 1 1 calc R U . . . C3 C 0.6183(2) 0.7504(3) 0.5635(6) 0.0587(12) Uani 1 1 d . . . . . C4 C 0.6801(2) 0.7755(3) 0.6374(6) 0.0615(13) Uani 1 1 d . . . . . H4 H 0.6909 0.8470 0.6568 0.074 Uiso 1 1 calc R U . . . C5 C 0.7244(2) 0.6981(3) 0.6811(6) 0.0612(13) Uani 1 1 d . . . . . H5 H 0.7653 0.7187 0.7259 0.073 Uiso 1 1 calc R U . . . C6 C 0.7110(2) 0.5874(3) 0.6614(5) 0.0535(12) Uani 1 1 d . . . . . C7 C 0.7595(2) 0.5074(3) 0.7072(5) 0.0536(11) Uani 1 1 d . . . . . C8 C 0.7485(2) 0.3979(3) 0.6926(6) 0.0569(12) Uani 1 1 d . . . . . C9 C 0.7983(2) 0.3224(3) 0.7432(6) 0.0684(14) Uani 1 1 d . . . . . H9 H 0.8379 0.3485 0.7879 0.082 Uiso 1 1 calc R U . . . C10 C 0.7905(2) 0.2157(4) 0.7292(6) 0.0722(15) Uani 1 1 d . . . . . H10 H 0.8248 0.1709 0.7649 0.087 Uiso 1 1 calc R U . . . C11 C 0.7315(2) 0.1692(4) 0.6612(7) 0.0739(15) Uani 1 1 d . . . . . C12 C 0.6798(2) 0.2450(3) 0.6099(6) 0.0729(15) Uani 1 1 d . . . . . H12 H 0.6403 0.2192 0.5635 0.087 Uiso 1 1 calc R U . . . C13 C 0.6884(2) 0.3511(3) 0.6286(6) 0.0561(12) Uani 1 1 d . . . . . C14 C 0.8236(2) 0.5479(3) 0.7815(6) 0.0519(11) Uani 1 1 d . . . . . C15 C 0.8785(2) 0.5700(3) 0.6911(6) 0.0563(11) Uani 1 1 d . . . . . C16 C 0.9356(2) 0.6096(3) 0.7652(6) 0.0620(13) Uani 1 1 d . . . . . H16 H 0.9718 0.6227 0.7015 0.074 Uiso 1 1 calc R U . . . C17 C 0.9390(2) 0.6294(4) 0.9306(6) 0.0605(13) Uani 1 1 d . . . . . C18 C 0.8858(2) 0.6089(4) 1.0241(6) 0.0714(14) Uani 1 1 d . . . . . H18 H 0.8880 0.6228 1.1377 0.086 Uiso 1 1 calc R U . . . C19 C 0.8292(2) 0.5677(4) 0.9507(6) 0.0670(14) Uani 1 1 d . . . . . H19 H 0.7938 0.5528 1.0162 0.080 Uiso 1 1 calc R U . . . C20 C 0.8784(3) 0.5506(5) 0.5093(7) 0.0776(16) Uani 1 1 d . . . . . C21 C 1.0478(3) 0.6962(5) 0.9238(7) 0.099(2) Uani 1 1 d . . . . . H21A H 1.0654 0.6316 0.8783 0.149 Uiso 1 1 calc R U . . . H21B H 1.0808 0.7304 0.9940 0.149 Uiso 1 1 calc R U . . . H21C H 1.0344 0.7438 0.8350 0.149 Uiso 1 1 calc R U . . . C22 C 0.5884(2) 0.9385(3) 0.5493(7) 0.0912(18) Uani 1 1 d . . . . . H22A H 0.5823 0.9523 0.6649 0.137 Uiso 1 1 calc R U . . . H22B H 0.5589 0.9824 0.4828 0.137 Uiso 1 1 calc R U . . . H22C H 0.6329 0.9548 0.5236 0.137 Uiso 1 1 calc R U . . . C23 C 0.5127(2) 0.8010(4) 0.4337(7) 0.0840(17) Uani 1 1 d . . . . . H23A H 0.5181 0.7434 0.3563 0.126 Uiso 1 1 calc R U . . . H23B H 0.4959 0.8630 0.3754 0.126 Uiso 1 1 calc R U . . . H23C H 0.4825 0.7797 0.5159 0.126 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0541(7) 0.0447(6) 0.0922(11) -0.0051(6) -0.0091(7) -0.0030(5) F1 0.094(3) 0.362(7) 0.057(3) 0.000(3) -0.015(2) 0.039(3) F2 0.270(6) 0.134(4) 0.102(3) -0.051(3) 0.020(3) -0.044(4) F3 0.109(3) 0.215(4) 0.069(3) -0.020(2) 0.013(2) -0.071(3) O1 0.132(3) 0.059(2) 0.104(3) -0.0117(19) -0.058(2) -0.0018(19) O2 0.065(2) 0.061(2) 0.147(4) -0.003(2) 0.044(2) -0.0077(16) O3 0.078(3) 0.0469(19) 0.205(5) -0.013(2) 0.007(3) 0.0021(17) O4 0.071(2) 0.113(3) 0.070(3) -0.008(2) -0.018(2) -0.017(2) N1 0.057(2) 0.043(2) 0.106(3) -0.010(2) -0.013(2) 0.0002(17) C1 0.047(2) 0.048(2) 0.070(3) -0.002(2) -0.004(2) -0.0035(19) C2 0.047(3) 0.046(2) 0.085(4) -0.004(2) -0.010(2) -0.0011(18) C3 0.050(3) 0.043(2) 0.082(4) 0.000(2) -0.001(2) 0.004(2) C4 0.053(3) 0.044(2) 0.088(4) -0.004(2) -0.003(3) -0.0046(19) C5 0.047(3) 0.051(3) 0.084(4) -0.001(2) -0.011(2) -0.0080(19) C6 0.054(3) 0.041(2) 0.065(3) 0.005(2) -0.003(2) -0.0022(18) C7 0.053(3) 0.050(2) 0.057(3) 0.000(2) -0.010(2) -0.0063(19) C8 0.048(3) 0.055(3) 0.068(4) 0.004(2) -0.002(2) -0.0024(19) C9 0.063(3) 0.059(3) 0.082(4) 0.007(3) -0.014(3) 0.004(2) C10 0.061(3) 0.058(3) 0.097(4) 0.013(3) -0.004(3) 0.008(2) C11 0.069(3) 0.049(3) 0.105(5) 0.002(3) 0.013(3) 0.004(2) C12 0.056(3) 0.048(3) 0.114(4) -0.008(3) 0.003(3) -0.002(2) C13 0.052(3) 0.044(2) 0.072(4) -0.002(2) 0.003(2) -0.0043(19) C14 0.054(3) 0.047(2) 0.053(3) 0.001(2) -0.004(2) -0.0019(19) C15 0.062(3) 0.058(3) 0.048(3) -0.006(2) -0.004(2) -0.006(2) C16 0.056(3) 0.079(3) 0.051(4) -0.006(2) -0.002(2) -0.007(2) C17 0.057(3) 0.068(3) 0.056(4) 0.000(2) -0.006(3) -0.011(2) C18 0.080(4) 0.084(3) 0.049(4) -0.005(3) -0.006(3) -0.011(3) C19 0.063(3) 0.070(3) 0.068(4) -0.001(3) 0.002(3) -0.012(2) C20 0.071(4) 0.088(4) 0.073(5) -0.011(3) 0.001(3) -0.025(3) C21 0.063(4) 0.126(5) 0.108(5) -0.005(4) -0.011(4) -0.023(3) C22 0.080(4) 0.044(3) 0.148(6) -0.005(3) -0.022(3) 0.002(2) C23 0.073(4) 0.063(3) 0.114(5) -0.008(3) -0.021(3) 0.004(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 O1 S1 O2 116.4(2) . . ? O1 S1 C1 110.4(2) . . ? O2 S1 C1 107.9(2) . . ? O1 S1 C13 109.9(2) . . ? O2 S1 C13 107.2(2) . . ? C1 S1 C13 104.5(2) . . ? C17 O4 C21 116.5(4) . . ? C3 N1 C23 122.4(4) . . ? C3 N1 C22 120.4(4) . . ? C23 N1 C22 117.1(4) . . ? C2 C1 C6 123.0(4) . . ? C2 C1 S1 114.8(3) . . ? C6 C1 S1 122.0(3) . . ? C1 C2 C3 121.0(4) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? N1 C3 C4 122.3(4) . . ? N1 C3 C2 121.5(4) . . ? C4 C3 C2 116.2(4) . . ? C5 C4 C3 121.8(4) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 122.7(4) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C1 C6 C5 115.1(4) . . ? C1 C6 C7 123.6(4) . . ? C5 C6 C7 121.3(4) . . ? C8 C7 C6 123.6(4) . . ? C8 C7 C14 119.9(4) . . ? C6 C7 C14 116.4(3) . . ? C7 C8 C9 120.9(4) . . ? C7 C8 C13 124.2(4) . . ? C9 C8 C13 114.8(4) . . ? C10 C9 C8 123.2(4) . . ? C10 C9 H9 118.4 . . ? C8 C9 H9 118.4 . . ? C9 C10 C11 122.0(4) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? O3 C11 C10 123.1(5) . . ? O3 C11 C12 121.2(5) . . ? C10 C11 C12 115.7(4) . . ? C13 C12 C11 121.0(5) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C8 123.2(4) . . ? C12 C13 S1 115.4(3) . . ? C8 C13 S1 121.3(3) . . ? C15 C14 C19 116.4(4) . . ? C15 C14 C7 124.5(4) . . ? C19 C14 C7 119.1(4) . . ? C14 C15 C16 122.0(5) . . ? C14 C15 C20 121.2(4) . . ? C16 C15 C20 116.8(5) . . ? C17 C16 C15 119.9(5) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 119.8(4) . . ? C16 C17 O4 124.9(4) . . ? C18 C17 O4 115.3(5) . . ? C17 C18 C19 120.3(5) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 121.6(5) . . ? C18 C19 H19 119.2 . . ? C14 C19 H19 119.2 . . ? F1 C20 F2 104.8(5) . . ? F1 C20 F3 106.7(5) . . ? F2 C20 F3 100.8(5) . . ? F1 C20 C15 116.2(5) . . ? F2 C20 C15 112.1(5) . . ? F3 C20 C15 114.7(4) . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N1 C22 H22A 109.5 . . ? N1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C23 H23A 109.5 . . ? N1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 S1 O1 1.424(3) . ? S1 O2 1.434(3) . ? S1 C1 1.755(4) . ? S1 C13 1.756(4) . ? F1 C20 1.288(6) . ? F2 C20 1.312(6) . ? F3 C20 1.305(5) . ? O3 C11 1.232(5) . ? O4 C17 1.385(5) . ? O4 C21 1.404(5) . ? N1 C3 1.343(5) . ? N1 C23 1.437(5) . ? N1 C22 1.449(5) . ? C1 C2 1.364(5) . ? C1 C6 1.406(5) . ? C2 C3 1.422(6) . ? C2 H2 0.9300 . ? C3 C4 1.405(6) . ? C4 C5 1.359(5) . ? C4 H4 0.9300 . ? C5 C6 1.414(5) . ? C5 H5 0.9300 . ? C6 C7 1.440(5) . ? C7 C8 1.388(5) . ? C7 C14 1.502(5) . ? C8 C9 1.430(5) . ? C8 C13 1.434(5) . ? C9 C10 1.344(5) . ? C9 H9 0.9300 . ? C10 C11 1.424(6) . ? C10 H10 0.9300 . ? C11 C12 1.463(6) . ? C12 C13 1.342(5) . ? C12 H12 0.9300 . ? C14 C15 1.388(6) . ? C14 C19 1.384(6) . ? C15 C16 1.377(6) . ? C15 C20 1.483(7) . ? C16 C17 1.353(6) . ? C16 H16 0.9300 . ? C17 C18 1.370(6) . ? C18 C19 1.373(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 C10 H10 F2 0.93 2.52 3.380(6) 153.7 4_566 C18 H18 F3 0.93 2.54 3.398(6) 154.1 1_556 C22 H22A O1 0.96 2.65 3.488(6) 146.3 4_576 C22 H22B O2 0.96 2.60 3.323(7) 132.0 4_575 C22 H22C O3 0.96 2.52 3.284(6) 136.5 1_565 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 O1 S1 C1 C2 56.8(4) . . . . ? O2 S1 C1 C2 -71.4(4) . . . . ? C13 S1 C1 C2 174.8(4) . . . . ? O1 S1 C1 C6 -127.5(4) . . . . ? O2 S1 C1 C6 104.3(4) . . . . ? C13 S1 C1 C6 -9.5(4) . . . . ? C6 C1 C2 C3 -0.7(7) . . . . ? S1 C1 C2 C3 175.0(3) . . . . ? C23 N1 C3 C4 178.1(5) . . . . ? C22 N1 C3 C4 -5.9(8) . . . . ? C23 N1 C3 C2 -2.5(8) . . . . ? C22 N1 C3 C2 173.5(4) . . . . ? C1 C2 C3 N1 178.8(4) . . . . ? C1 C2 C3 C4 -1.8(7) . . . . ? N1 C3 C4 C5 -177.3(5) . . . . ? C2 C3 C4 C5 3.2(8) . . . . ? C3 C4 C5 C6 -2.3(8) . . . . ? C2 C1 C6 C5 1.6(7) . . . . ? S1 C1 C6 C5 -173.7(3) . . . . ? C2 C1 C6 C7 -177.7(4) . . . . ? S1 C1 C6 C7 6.9(7) . . . . ? C4 C5 C6 C1 -0.1(7) . . . . ? C4 C5 C6 C7 179.2(4) . . . . ? C1 C6 C7 C8 -1.6(7) . . . . ? C5 C6 C7 C8 179.1(4) . . . . ? C1 C6 C7 C14 -178.8(4) . . . . ? C5 C6 C7 C14 1.9(6) . . . . ? C6 C7 C8 C9 -178.8(4) . . . . ? C14 C7 C8 C9 -1.7(7) . . . . ? C6 C7 C8 C13 0.8(7) . . . . ? C14 C7 C8 C13 177.9(4) . . . . ? C7 C8 C9 C10 -178.9(5) . . . . ? C13 C8 C9 C10 1.4(7) . . . . ? C8 C9 C10 C11 0.3(8) . . . . ? C9 C10 C11 O3 178.6(5) . . . . ? C9 C10 C11 C12 -0.8(8) . . . . ? O3 C11 C12 C13 179.9(5) . . . . ? C10 C11 C12 C13 -0.7(7) . . . . ? C11 C12 C13 C8 2.6(8) . . . . ? C11 C12 C13 S1 -174.7(4) . . . . ? C7 C8 C13 C12 177.5(4) . . . . ? C9 C8 C13 C12 -2.9(7) . . . . ? C7 C8 C13 S1 -5.4(7) . . . . ? C9 C8 C13 S1 174.3(3) . . . . ? O1 S1 C13 C12 -55.6(4) . . . . ? O2 S1 C13 C12 71.7(4) . . . . ? C1 S1 C13 C12 -173.9(4) . . . . ? O1 S1 C13 C8 127.1(4) . . . . ? O2 S1 C13 C8 -105.6(4) . . . . ? C1 S1 C13 C8 8.7(4) . . . . ? C8 C7 C14 C15 89.9(5) . . . . ? C6 C7 C14 C15 -92.8(5) . . . . ? C8 C7 C14 C19 -91.7(5) . . . . ? C6 C7 C14 C19 85.6(5) . . . . ? C19 C14 C15 C16 -0.1(6) . . . . ? C7 C14 C15 C16 178.3(4) . . . . ? C19 C14 C15 C20 179.2(4) . . . . ? C7 C14 C15 C20 -2.3(7) . . . . ? C14 C15 C16 C17 -0.8(7) . . . . ? C20 C15 C16 C17 179.8(4) . . . . ? C15 C16 C17 C18 0.7(7) . . . . ? C15 C16 C17 O4 -178.8(4) . . . . ? C21 O4 C17 C16 1.7(7) . . . . ? C21 O4 C17 C18 -177.9(4) . . . . ? C16 C17 C18 C19 0.4(7) . . . . ? O4 C17 C18 C19 180.0(4) . . . . ? C17 C18 C19 C14 -1.4(7) . . . . ? C15 C14 C19 C18 1.2(7) . . . . ? C7 C14 C19 C18 -177.3(4) . . . . ? C14 C15 C20 F1 44.2(7) . . . . ? C16 C15 C20 F1 -136.5(5) . . . . ? C14 C15 C20 F2 -76.3(6) . . . . ? C16 C15 C20 F2 103.1(6) . . . . ? C14 C15 C20 F3 169.5(5) . . . . ? C16 C15 C20 F3 -11.1(7) . . . . ?