#------------------------------------------------------------------------------ #$Date: 2024-09-06 02:57:50 +0300 (Fri, 06 Sep 2024) $ #$Revision: 294493 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/22/1572217.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_1572217 loop_ _publ_author_name 'Zhu, Mengliang' 'Zhang, Hang' 'Yao, Yuhang' 'Wen, Mingpu' 'Ran, Guangliu' 'Yu, Yi' 'Zhang, Ruijing' 'Liang, Xing-Jie' 'Zhang, Jing' 'Zhang, Wenkai' 'Zhang, Jun-Long' _publ_section_title ; More is different: progressive β-thiolation induced-porphyrin aggregation switches singlet oxygen photosensitization. ; _journal_issue 34 _journal_name_full 'Chemical science' _journal_page_first 13841 _journal_page_last 13852 _journal_paper_doi 10.1039/d4sc03642e _journal_volume 15 _journal_year 2024 _chemical_formula_sum 'C46 H12 F20 N6 O2 S2' _chemical_formula_weight 1124.74 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2023-05-09 deposited with the CCDC. 2024-07-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.9737(2) _cell_length_b 16.1898(3) _cell_length_c 22.2877(3) _cell_measurement_reflns_used 20911 _cell_measurement_temperature 179.99(10) _cell_measurement_theta_max 30.5220 _cell_measurement_theta_min 2.2730 _cell_volume 4320.51(12) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 179.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.926 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_unetI/netI 0.0164 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.926 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 52873 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.926 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.687 _diffrn_reflns_theta_min 1.827 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.73341 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.729 _exptl_crystal_description plate-like _exptl_crystal_F_000 2232 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.958 _refine_diff_density_min -0.794 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 344 _refine_ls_number_reflns 6198 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0498 _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^)+(0.0828P)^2^+2.7998P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1439 _refine_ls_wR_factor_ref 0.1520 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5030 _reflns_number_total 6198 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc03642e2.cif _cod_data_source_block 3 _cod_depositor_comments 'Adding full bibliography for 1572215--1572218.cif.' _cod_database_code 1572217 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _oxdiff_exptl_absorpt_empirical_full_min 0.704 _oxdiff_exptl_absorpt_empirical_full_max 1.266 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; 3.res created by SHELXL-2014/7 TITL 3_a.res in Pbca REM Old TITL 3 in Pbca REM SHELXT solution in Pbca REM R1 0.156, Rweak 0.007, Alpha 0.024, Orientation as input REM Formula found by SHELXT: C23 N3 O F10 S CELL 0.71073 11.9737 16.1898 22.2877 90 90 90 ZERR 4 0.0002 0.0003 0.0003 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O F S UNIT 184 48 24 8 80 8 L.S. 10 PLAN 6 CONF BOND $H LIST 4 fmap 2 acta WGHT 0.082800 2.799800 FVAR 0.18989 S1 6 -0.009554 0.180601 0.623486 11.00000 0.05104 0.03230 = 0.04150 0.00475 0.01329 0.00259 F1 5 0.267006 0.244991 0.571880 11.00000 0.04189 0.04916 = 0.05153 -0.00168 -0.01516 -0.00696 F2 5 0.337080 0.086900 0.580580 11.00000 0.04268 0.06821 = 0.06014 0.01394 -0.00758 0.02012 F3 5 0.230112 -0.034057 0.518363 11.00000 0.08211 0.03561 = 0.05099 0.00725 0.02024 0.02817 F4 5 0.061258 0.004722 0.443378 11.00000 0.08684 0.02946 = 0.04173 -0.01109 0.00276 -0.00477 F5 5 -0.012993 0.161962 0.436316 11.00000 0.05038 0.03853 = 0.03998 -0.00639 -0.01618 0.00168 F6 5 0.329597 0.614875 0.345792 11.00000 0.04622 0.05833 = 0.02925 -0.00557 -0.00470 -0.01827 F7 5 0.418377 0.641548 0.236551 11.00000 0.04710 0.06932 = 0.04875 0.00086 0.01500 -0.02736 F8 5 0.312437 0.587046 0.137222 11.00000 0.07683 0.07087 = 0.02537 -0.00040 0.02088 -0.01997 F9 5 0.118111 0.501605 0.147316 11.00000 0.07610 0.08347 = 0.02181 -0.00991 -0.00461 -0.02727 F10 5 0.029361 0.472931 0.256576 11.00000 0.04061 0.06240 = 0.03524 -0.00517 0.00068 -0.02256 O1 4 -0.078914 0.331264 0.636086 11.00000 0.03264 0.02762 = 0.02189 0.00112 0.00393 -0.00108 N1 3 -0.021631 0.402831 0.554243 11.00000 0.02837 0.02395 = 0.01848 -0.00236 0.00205 0.00080 N2 3 0.085754 0.421460 0.441074 11.00000 0.02990 0.02540 = 0.01976 -0.00202 0.00552 0.00246 AFIX 43 H2 2 0.043748 0.451149 0.463758 11.00000 -1.20000 AFIX 0 C1 1 -0.075769 0.405827 0.606342 11.00000 0.02720 0.02619 = 0.01866 -0.00037 0.00146 -0.00102 C2 1 -0.020114 0.275385 0.601432 11.00000 0.02810 0.02550 = 0.02451 0.00017 -0.00007 -0.00191 C3 1 0.016496 0.323626 0.549131 11.00000 0.02630 0.02395 = 0.02063 -0.00182 0.00066 -0.00082 C4 1 0.082351 0.294108 0.501762 11.00000 0.02758 0.02478 = 0.02180 -0.00298 0.00059 0.00064 C5 1 0.114045 0.340972 0.452080 11.00000 0.02732 0.02548 = 0.02190 -0.00288 0.00292 0.00157 C6 1 0.183366 0.314995 0.403300 11.00000 0.03773 0.02936 = 0.02757 -0.00321 0.00880 0.00612 AFIX 43 H6 2 0.215228 0.262982 0.398761 11.00000 -1.20000 AFIX 0 C7 1 0.194574 0.379562 0.364729 11.00000 0.03892 0.03180 = 0.02494 -0.00247 0.01056 0.00494 AFIX 43 H7 2 0.234667 0.379258 0.328992 11.00000 -1.20000 AFIX 0 C8 1 0.133879 0.447945 0.388802 11.00000 0.02876 0.02870 = 0.01984 -0.00282 0.00438 0.00094 C9 1 0.127422 0.527354 0.364927 11.00000 0.02855 0.02802 = 0.01854 -0.00206 0.00392 -0.00084 C10 1 0.124987 0.207625 0.503965 11.00000 0.02944 0.02548 = 0.02251 -0.00060 0.00523 0.00206 C11 1 0.215569 0.186427 0.539417 11.00000 0.02818 0.03592 = 0.03059 0.00012 0.00229 0.00044 C12 1 0.251558 0.105765 0.544509 11.00000 0.03213 0.04496 = 0.03372 0.00880 0.00622 0.01222 C13 1 0.198553 0.044716 0.512685 11.00000 0.04932 0.03024 = 0.03263 0.00516 0.01650 0.01478 C14 1 0.110943 0.064102 0.475108 11.00000 0.05289 0.02560 = 0.02702 -0.00343 0.00930 0.00227 C15 1 0.074932 0.145166 0.471462 11.00000 0.03697 0.02929 = 0.02403 -0.00183 0.00163 0.00200 C16 1 0.177233 0.542190 0.304644 11.00000 0.02986 0.02573 = 0.01941 -0.00235 0.00495 0.00110 C17 1 0.276091 0.585673 0.297594 11.00000 0.03271 0.03285 = 0.02215 -0.00314 0.00177 -0.00372 C18 1 0.321857 0.600361 0.241659 11.00000 0.03507 0.03817 = 0.03136 -0.00039 0.00937 -0.00850 C19 1 0.267839 0.572619 0.191213 11.00000 0.04968 0.04069 = 0.02150 -0.00034 0.01254 -0.00457 C20 1 0.169849 0.529247 0.196485 11.00000 0.04861 0.04448 = 0.01939 -0.00564 0.00017 -0.00703 C21 1 0.125777 0.514636 0.252783 11.00000 0.03215 0.03520 = 0.02546 -0.00282 0.00287 -0.00614 N3 3 0.764016 0.828040 0.278447 11.00000 0.08929 0.21827 = 0.07649 0.05917 0.00098 -0.04217 C22 1 0.675648 0.806453 0.288703 11.00000 0.07944 0.08167 = 0.04577 0.01881 -0.00094 -0.01123 C23 1 0.564829 0.781352 0.302777 11.00000 0.07299 0.08522 = 0.08726 0.01767 -0.01255 -0.01968 AFIX 137 H23A 2 0.520978 0.779750 0.266736 11.00000 -1.50000 H23B 2 0.532359 0.819952 0.330433 11.00000 -1.50000 H23C 2 0.566375 0.727419 0.320659 11.00000 -1.50000 AFIX 0 HKLF 4 REM 3_a.res in Pbca REM R1 = 0.0498 for 5030 Fo > 4sig(Fo) and 0.0622 for all 6198 data REM 344 parameters refined using 0 restraints END WGHT 0.0813 2.8622 REM Highest difference peak 0.958, deepest hole -0.794, 1-sigma level 0.066 Q1 1 -0.1109 0.2657 0.6859 11.00000 0.05 0.96 Q2 1 0.7390 0.7744 0.2619 11.00000 0.05 0.44 Q3 1 -0.0061 0.2356 0.6121 11.00000 0.05 0.42 Q4 1 0.0042 0.2926 0.5740 11.00000 0.05 0.39 Q5 1 0.2956 0.5911 0.2700 11.00000 0.05 0.38 Q6 1 0.1750 0.4218 0.3775 11.00000 0.05 0.37 ; _shelx_res_checksum 45960 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.00955(5) 0.18060(3) 0.62349(2) 0.04161(15) Uani 1 1 d . . . . . F1 F 0.26701(11) 0.24499(9) 0.57188(6) 0.0475(3) Uani 1 1 d . . . . . F2 F 0.33708(11) 0.08690(10) 0.58058(7) 0.0570(4) Uani 1 1 d . . . . . F3 F 0.23011(14) -0.03406(8) 0.51836(6) 0.0562(4) Uani 1 1 d . . . . . F4 F 0.06126(14) 0.00472(8) 0.44338(6) 0.0527(4) Uani 1 1 d . . . . . F5 F -0.01299(11) 0.16196(8) 0.43632(6) 0.0430(3) Uani 1 1 d . . . . . F6 F 0.32960(11) 0.61488(9) 0.34579(5) 0.0446(3) Uani 1 1 d . . . . . F7 F 0.41838(12) 0.64155(10) 0.23655(6) 0.0551(4) Uani 1 1 d . . . . . F8 F 0.31244(13) 0.58705(10) 0.13722(6) 0.0577(4) Uani 1 1 d . . . . . F9 F 0.11811(14) 0.50161(11) 0.14732(6) 0.0605(4) Uani 1 1 d . . . . . F10 F 0.02936(10) 0.47293(9) 0.25658(6) 0.0461(3) Uani 1 1 d . . . . . O1 O -0.07891(10) 0.33126(8) 0.63609(5) 0.0274(3) Uani 1 1 d . . . . . N1 N -0.02163(12) 0.40283(9) 0.55424(6) 0.0236(3) Uani 1 1 d . . . . . N2 N 0.08575(12) 0.42146(9) 0.44107(6) 0.0250(3) Uani 1 1 d . . . . . H2 H 0.0437 0.4511 0.4638 0.030 Uiso 1 1 calc R U . . . C1 C -0.07577(13) 0.40583(10) 0.60634(7) 0.0240(3) Uani 1 1 d . . . . . C2 C -0.02011(14) 0.27538(11) 0.60143(7) 0.0260(3) Uani 1 1 d . . . . . C3 C 0.01650(14) 0.32363(10) 0.54913(7) 0.0236(3) Uani 1 1 d . . . . . C4 C 0.08235(14) 0.29411(10) 0.50176(7) 0.0247(3) Uani 1 1 d . . . . . C5 C 0.11404(14) 0.34097(10) 0.45208(7) 0.0249(3) Uani 1 1 d . . . . . C6 C 0.18337(16) 0.31500(12) 0.40330(8) 0.0316(4) Uani 1 1 d . . . . . H6 H 0.2152 0.2630 0.3988 0.038 Uiso 1 1 calc R U . . . C7 C 0.19457(16) 0.37956(12) 0.36473(8) 0.0319(4) Uani 1 1 d . . . . . H7 H 0.2347 0.3793 0.3290 0.038 Uiso 1 1 calc R U . . . C8 C 0.13388(14) 0.44795(11) 0.38880(7) 0.0258(3) Uani 1 1 d . . . . . C9 C 0.12742(14) 0.52735(10) 0.36493(7) 0.0250(3) Uani 1 1 d . . . . . C10 C 0.12499(14) 0.20762(10) 0.50396(7) 0.0258(3) Uani 1 1 d . . . . . C11 C 0.21557(15) 0.18643(12) 0.53942(8) 0.0316(4) Uani 1 1 d . . . . . C12 C 0.25156(16) 0.10576(14) 0.54451(9) 0.0369(4) Uani 1 1 d . . . . . C13 C 0.19855(18) 0.04472(12) 0.51268(9) 0.0374(4) Uani 1 1 d . . . . . C14 C 0.11094(18) 0.06410(11) 0.47511(8) 0.0352(4) Uani 1 1 d . . . . . C15 C 0.07493(16) 0.14517(11) 0.47146(8) 0.0301(4) Uani 1 1 d . . . . . C16 C 0.17723(14) 0.54219(10) 0.30464(7) 0.0250(3) Uani 1 1 d . . . . . C17 C 0.27609(15) 0.58567(11) 0.29759(7) 0.0292(3) Uani 1 1 d . . . . . C18 C 0.32186(16) 0.60036(13) 0.24166(9) 0.0349(4) Uani 1 1 d . . . . . C19 C 0.26784(18) 0.57262(13) 0.19121(8) 0.0373(4) Uani 1 1 d . . . . . C20 C 0.16985(18) 0.52925(14) 0.19649(8) 0.0375(4) Uani 1 1 d . . . . . C21 C 0.12578(15) 0.51464(12) 0.25278(8) 0.0309(4) Uani 1 1 d . . . . . N3 N 0.7640(3) 0.8280(3) 0.27845(17) 0.1280(17) Uani 1 1 d . . . . . C22 C 0.6756(3) 0.8065(2) 0.28870(13) 0.0690(8) Uani 1 1 d . . . . . C23 C 0.5648(3) 0.7814(3) 0.30278(18) 0.0818(10) Uani 1 1 d . . . . . H23A H 0.5210 0.7797 0.2667 0.123 Uiso 1 1 calc R U . . . H23B H 0.5324 0.8200 0.3304 0.123 Uiso 1 1 calc R U . . . H23C H 0.5664 0.7274 0.3207 0.123 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 0.0510(3) 0.0323(3) 0.0415(3) 0.00475(19) 0.0133(2) 0.0026(2) F1 0.0419(7) 0.0492(7) 0.0515(7) -0.0017(6) -0.0152(6) -0.0070(6) F2 0.0427(7) 0.0682(10) 0.0601(9) 0.0139(7) -0.0076(6) 0.0201(7) F3 0.0821(10) 0.0356(7) 0.0510(8) 0.0073(6) 0.0202(7) 0.0282(7) F4 0.0868(11) 0.0295(6) 0.0417(7) -0.0111(5) 0.0028(7) -0.0048(6) F5 0.0504(7) 0.0385(6) 0.0400(6) -0.0064(5) -0.0162(5) 0.0017(5) F6 0.0462(7) 0.0583(8) 0.0293(6) -0.0056(5) -0.0047(5) -0.0183(6) F7 0.0471(8) 0.0693(9) 0.0488(8) 0.0009(7) 0.0150(6) -0.0274(7) F8 0.0768(10) 0.0709(10) 0.0254(6) -0.0004(6) 0.0209(6) -0.0200(8) F9 0.0761(10) 0.0835(11) 0.0218(6) -0.0099(6) -0.0046(6) -0.0273(8) F10 0.0406(7) 0.0624(8) 0.0352(6) -0.0052(6) 0.0007(5) -0.0226(6) O1 0.0326(6) 0.0276(6) 0.0219(5) 0.0011(4) 0.0039(4) -0.0011(5) N1 0.0284(7) 0.0240(6) 0.0185(6) -0.0024(5) 0.0020(5) 0.0008(5) N2 0.0299(7) 0.0254(7) 0.0198(6) -0.0020(5) 0.0055(5) 0.0025(5) C1 0.0272(7) 0.0262(8) 0.0187(7) -0.0004(6) 0.0015(6) -0.0010(6) C2 0.0281(8) 0.0255(8) 0.0245(7) 0.0002(6) -0.0001(6) -0.0019(6) C3 0.0263(7) 0.0239(7) 0.0206(7) -0.0018(6) 0.0007(6) -0.0008(6) C4 0.0276(7) 0.0248(8) 0.0218(7) -0.0030(6) 0.0006(6) 0.0006(6) C5 0.0273(7) 0.0255(8) 0.0219(7) -0.0029(6) 0.0029(6) 0.0016(6) C6 0.0377(9) 0.0294(8) 0.0276(8) -0.0032(6) 0.0088(7) 0.0061(7) C7 0.0389(9) 0.0318(9) 0.0249(8) -0.0025(6) 0.0106(7) 0.0049(7) C8 0.0288(8) 0.0287(8) 0.0198(7) -0.0028(6) 0.0044(6) 0.0009(6) C9 0.0285(8) 0.0280(8) 0.0185(7) -0.0021(6) 0.0039(6) -0.0008(6) C10 0.0294(8) 0.0255(8) 0.0225(7) -0.0006(6) 0.0052(6) 0.0021(6) C11 0.0282(8) 0.0359(9) 0.0306(8) 0.0001(7) 0.0023(7) 0.0004(7) C12 0.0321(9) 0.0450(11) 0.0337(9) 0.0088(8) 0.0062(7) 0.0122(8) C13 0.0493(11) 0.0302(9) 0.0326(9) 0.0052(7) 0.0165(8) 0.0148(8) C14 0.0529(11) 0.0256(8) 0.0270(8) -0.0034(6) 0.0093(8) 0.0023(8) C15 0.0370(9) 0.0293(8) 0.0240(7) -0.0018(6) 0.0016(6) 0.0020(7) C16 0.0299(8) 0.0257(8) 0.0194(7) -0.0024(6) 0.0050(6) 0.0011(6) C17 0.0327(8) 0.0328(9) 0.0222(7) -0.0031(6) 0.0018(6) -0.0037(7) C18 0.0351(9) 0.0382(10) 0.0314(9) -0.0004(7) 0.0094(7) -0.0085(8) C19 0.0497(11) 0.0407(10) 0.0215(8) -0.0003(7) 0.0125(7) -0.0046(8) C20 0.0486(11) 0.0445(11) 0.0194(7) -0.0056(7) 0.0002(7) -0.0070(9) C21 0.0322(9) 0.0352(9) 0.0255(8) -0.0028(7) 0.0029(6) -0.0061(7) N3 0.089(2) 0.218(5) 0.076(2) 0.059(3) 0.0010(18) -0.042(3) C22 0.079(2) 0.082(2) 0.0458(14) 0.0188(14) -0.0009(14) -0.0112(17) C23 0.073(2) 0.085(2) 0.087(2) 0.0177(19) -0.0125(18) -0.0197(18) 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 C1 O1 C2 106.90(12) . . ? C1 N1 C3 105.65(14) . . ? C5 N2 C8 110.28(14) . . ? C5 N2 H2 124.9 . . ? C8 N2 H2 124.9 . . ? N1 C1 O1 113.66(14) . . ? N1 C1 C9 129.94(15) . 5_566 ? O1 C1 C9 116.40(14) . 5_566 ? O1 C2 C3 104.31(14) . . ? O1 C2 S1 119.43(12) . . ? C3 C2 S1 136.24(13) . . ? N1 C3 C4 124.81(15) . . ? N1 C3 C2 109.45(14) . . ? C4 C3 C2 125.72(15) . . ? C5 C4 C3 124.44(15) . . ? C5 C4 C10 116.34(14) . . ? C3 C4 C10 119.20(14) . . ? N2 C5 C4 126.36(15) . . ? N2 C5 C6 106.69(14) . . ? C4 C5 C6 126.94(16) . . ? C7 C6 C5 108.15(15) . . ? C7 C6 H6 125.9 . . ? C5 C6 H6 125.9 . . ? C6 C7 C8 107.94(15) . . ? C6 C7 H7 126.0 . . ? C8 C7 H7 126.0 . . ? N2 C8 C9 126.21(15) . . ? N2 C8 C7 106.92(15) . . ? C9 C8 C7 126.84(15) . . ? C8 C9 C1 124.21(14) . 5_566 ? C8 C9 C16 118.10(14) . . ? C1 C9 C16 117.68(15) 5_566 . ? C15 C10 C11 117.24(16) . . ? C15 C10 C4 121.45(15) . . ? C11 C10 C4 121.30(16) . . ? F1 C11 C12 118.74(17) . . ? F1 C11 C10 119.46(17) . . ? C12 C11 C10 121.73(18) . . ? F2 C12 C13 120.03(19) . . ? F2 C12 C11 120.3(2) . . ? C13 C12 C11 119.65(18) . . ? F3 C13 C12 120.5(2) . . ? F3 C13 C14 119.3(2) . . ? C12 C13 C14 120.13(17) . . ? F4 C14 C13 119.84(18) . . ? F4 C14 C15 120.90(19) . . ? C13 C14 C15 119.26(18) . . ? F5 C15 C10 119.94(16) . . ? F5 C15 C14 118.13(17) . . ? C10 C15 C14 121.90(18) . . ? C21 C16 C17 116.70(15) . . ? C21 C16 C9 121.55(15) . . ? C17 C16 C9 121.74(15) . . ? F6 C17 C18 118.28(16) . . ? F6 C17 C16 119.85(15) . . ? C18 C17 C16 121.88(16) . . ? F7 C18 C19 120.00(17) . . ? F7 C18 C17 120.29(17) . . ? C19 C18 C17 119.71(17) . . ? F8 C19 C20 120.52(18) . . ? F8 C19 C18 119.46(18) . . ? C20 C19 C18 120.01(16) . . ? F9 C20 C19 119.84(17) . . ? F9 C20 C21 120.69(18) . . ? C19 C20 C21 119.47(17) . . ? F10 C21 C20 118.20(16) . . ? F10 C21 C16 119.56(15) . . ? C20 C21 C16 122.23(17) . . ? N3 C22 C23 178.3(5) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 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 C2 1.6163(18) . ? F1 C11 1.342(2) . ? F2 C12 1.337(2) . ? F3 C13 1.336(2) . ? F4 C14 1.334(2) . ? F5 C15 1.340(2) . ? F6 C17 1.337(2) . ? F7 C18 1.339(2) . ? F8 C19 1.337(2) . ? F9 C20 1.336(2) . ? F10 C21 1.340(2) . ? O1 C1 1.378(2) . ? O1 C2 1.382(2) . ? N1 C1 1.331(2) . ? N1 C3 1.366(2) . ? N2 C5 1.369(2) . ? N2 C8 1.369(2) . ? N2 H2 0.8600 . ? C1 C9 1.401(2) 5_566 ? C2 C3 1.470(2) . ? C3 C4 1.402(2) . ? C4 C5 1.395(2) . ? C4 C10 1.491(2) . ? C5 C6 1.431(2) . ? C6 C7 1.360(3) . ? C6 H6 0.9300 . ? C7 C8 1.429(2) . ? C7 H7 0.9300 . ? C8 C9 1.394(2) . ? C9 C1 1.401(2) 5_566 ? C9 C16 1.489(2) . ? C10 C15 1.381(2) . ? C10 C11 1.385(3) . ? C11 C12 1.380(3) . ? C12 C13 1.372(3) . ? C13 C14 1.379(3) . ? C14 C15 1.384(3) . ? C16 C21 1.384(2) . ? C16 C17 1.386(2) . ? C17 C18 1.382(2) . ? C18 C19 1.373(3) . ? C19 C20 1.372(3) . ? C20 C21 1.382(3) . ? N3 C22 1.138(5) . ? C22 C23 1.423(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 C3 N1 C1 O1 -1.82(18) . . . . ? C3 N1 C1 C9 177.13(17) . . . 5_566 ? C2 O1 C1 N1 1.41(18) . . . . ? C2 O1 C1 C9 -177.69(14) . . . 5_566 ? C1 O1 C2 C3 -0.37(17) . . . . ? C1 O1 C2 S1 -179.03(12) . . . . ? C1 N1 C3 C4 -177.23(16) . . . . ? C1 N1 C3 C2 1.50(18) . . . . ? O1 C2 C3 N1 -0.69(18) . . . . ? S1 C2 C3 N1 177.61(15) . . . . ? O1 C2 C3 C4 178.02(15) . . . . ? S1 C2 C3 C4 -3.7(3) . . . . ? N1 C3 C4 C5 -2.8(3) . . . . ? C2 C3 C4 C5 178.71(16) . . . . ? N1 C3 C4 C10 175.71(15) . . . . ? C2 C3 C4 C10 -2.8(2) . . . . ? C8 N2 C5 C4 178.57(16) . . . . ? C8 N2 C5 C6 -0.64(19) . . . . ? C3 C4 C5 N2 -0.8(3) . . . . ? C10 C4 C5 N2 -179.36(15) . . . . ? C3 C4 C5 C6 178.20(17) . . . . ? C10 C4 C5 C6 -0.3(3) . . . . ? N2 C5 C6 C7 -0.1(2) . . . . ? C4 C5 C6 C7 -179.33(18) . . . . ? C5 C6 C7 C8 0.8(2) . . . . ? C5 N2 C8 C9 -177.01(17) . . . . ? C5 N2 C8 C7 1.13(19) . . . . ? C6 C7 C8 N2 -1.2(2) . . . . ? C6 C7 C8 C9 176.93(18) . . . . ? N2 C8 C9 C1 4.5(3) . . . 5_566 ? C7 C8 C9 C1 -173.29(17) . . . 5_566 ? N2 C8 C9 C16 -174.68(16) . . . . ? C7 C8 C9 C16 7.5(3) . . . . ? C5 C4 C10 C15 -80.1(2) . . . . ? C3 C4 C10 C15 101.31(19) . . . . ? C5 C4 C10 C11 100.84(19) . . . . ? C3 C4 C10 C11 -77.8(2) . . . . ? C15 C10 C11 F1 -179.97(16) . . . . ? C4 C10 C11 F1 -0.9(3) . . . . ? C15 C10 C11 C12 -3.0(3) . . . . ? C4 C10 C11 C12 176.12(16) . . . . ? F1 C11 C12 F2 -0.9(3) . . . . ? C10 C11 C12 F2 -177.88(17) . . . . ? F1 C11 C12 C13 178.62(17) . . . . ? C10 C11 C12 C13 1.6(3) . . . . ? F2 C12 C13 F3 1.4(3) . . . . ? C11 C12 C13 F3 -178.05(17) . . . . ? F2 C12 C13 C14 -179.49(17) . . . . ? C11 C12 C13 C14 1.0(3) . . . . ? F3 C13 C14 F4 -2.3(3) . . . . ? C12 C13 C14 F4 178.64(17) . . . . ? F3 C13 C14 C15 176.95(17) . . . . ? C12 C13 C14 C15 -2.1(3) . . . . ? C11 C10 C15 F5 -179.94(16) . . . . ? C4 C10 C15 F5 1.0(3) . . . . ? C11 C10 C15 C14 1.8(3) . . . . ? C4 C10 C15 C14 -177.27(16) . . . . ? F4 C14 C15 F5 1.6(3) . . . . ? C13 C14 C15 F5 -177.59(17) . . . . ? F4 C14 C15 C10 179.90(17) . . . . ? C13 C14 C15 C10 0.7(3) . . . . ? C8 C9 C16 C21 74.6(2) . . . . ? C1 C9 C16 C21 -104.7(2) 5_566 . . . ? C8 C9 C16 C17 -106.8(2) . . . . ? C1 C9 C16 C17 74.0(2) 5_566 . . . ? C21 C16 C17 F6 179.28(17) . . . . ? C9 C16 C17 F6 0.6(3) . . . . ? C21 C16 C17 C18 -0.5(3) . . . . ? C9 C16 C17 C18 -179.24(17) . . . . ? F6 C17 C18 F7 1.2(3) . . . . ? C16 C17 C18 F7 -179.01(18) . . . . ? F6 C17 C18 C19 -178.72(19) . . . . ? C16 C17 C18 C19 1.1(3) . . . . ? F7 C18 C19 F8 0.0(3) . . . . ? C17 C18 C19 F8 179.95(19) . . . . ? F7 C18 C19 C20 178.9(2) . . . . ? C17 C18 C19 C20 -1.1(3) . . . . ? F8 C19 C20 F9 -0.4(3) . . . . ? C18 C19 C20 F9 -179.3(2) . . . . ? F8 C19 C20 C21 179.6(2) . . . . ? C18 C19 C20 C21 0.7(3) . . . . ? F9 C20 C21 F10 -0.8(3) . . . . ? C19 C20 C21 F10 179.26(19) . . . . ? F9 C20 C21 C16 179.86(19) . . . . ? C19 C20 C21 C16 -0.1(3) . . . . ? C17 C16 C21 F10 -179.33(17) . . . . ? C9 C16 C21 F10 -0.6(3) . . . . ? C17 C16 C21 C20 0.0(3) . . . . ? C9 C16 C21 C20 178.76(18) . . . . ?