#------------------------------------------------------------------------------ #$Date: 2024-10-04 01:09:57 +0300 (Fri, 04 Oct 2024) $ #$Revision: 295021 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/27/1572751.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_1572751 loop_ _publ_author_name 'Anju, B. S.' 'Nair, Neeraja R.' 'Rajput, Janavi' 'Bertke, Jeffery A.' 'Mondal, Bhaskar' 'Kundu, Subrata' _publ_section_title ; Role of Ancillary Ligands in S-nitrosothiol and NO Generation from Nitrite-Thiol Interactions at Mononuclear Zinc(II) Sites ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC04853A _journal_year 2024 _chemical_absolute_configuration unk _chemical_formula_moiety 'C23 H32 F3 N8 O3 S Zn, C F3 O3 S' _chemical_formula_sum 'C24 H32 F6 N8 O6 S2 Zn' _chemical_formula_weight 772.06 _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 geom _atom_sites_solution_primary intrinsic _audit_creation_method SHELXL-2019/1 _audit_update_record ; 2024-05-16 deposited with the CCDC. 2024-10-03 downloaded from the CCDC. ; _cell_angle_alpha 68.674(4) _cell_angle_beta 81.829(4) _cell_angle_gamma 82.012(4) _cell_formula_units_Z 1 _cell_length_a 8.4126(12) _cell_length_b 8.7175(12) _cell_length_c 11.8242(16) _cell_measurement_reflns_used 6090 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 23.43 _cell_measurement_theta_min 2.46 _cell_volume 795.98(19) _computing_cell_refinement 'SAINT V8.37A (Bruker, 2005)' _computing_data_collection 'APEX3 V2016.5-0 (Bruker, 2016)' _computing_data_reduction ; SAINT V8.37A, XPREP v2014/2, TWINABS V2012/1 (Bruker, 2016) ; _computing_molecular_graphics 'SHELXLE v932 (Hubschle, 2011)' _computing_publication_material 'XCIF V2014-2 (Bruker, 2014)' _computing_structure_refinement 'SHELXL-2019/1 (Sheldrick, 2019)' _computing_structure_solution 'SHELX-2014-5 (Sheldrick, 2015)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker ApexII CCD' _diffrn_measurement_method 'profile data from \f and \w scans' _diffrn_radiation_monochromator 'multilayer mirrors' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0810 _diffrn_reflns_av_unetI/netI 0.0643 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_number 4035 _diffrn_reflns_point_group_measured_fraction_full 0.500 _diffrn_reflns_point_group_measured_fraction_max 0.492 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.667 _diffrn_reflns_theta_min 2.457 _exptl_absorpt_coefficient_mu 0.990 _exptl_absorpt_correction_T_max 0.745687 _exptl_absorpt_correction_T_min 0.582712 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2016/2 (Bruker, 2016)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 396 _exptl_crystal_size_max 0.090 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.543 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.091 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.48(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 433 _refine_ls_number_reflns 4035 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0450 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0588P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0976 _refine_ls_wR_factor_ref 0.1039 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full 0.000 _reflns_Friedel_fraction_max 0.000 _reflns_number_gt 3298 _reflns_number_total 4035 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc04853a2.cif _cod_data_source_block ABS1407 _cod_database_code 1572751 _shelx_shelxl_version_number 2019/1 _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 0.916 _shelx_estimated_absorpt_t_max 0.952 _shelx_res_file ; TITL abs1407_a.res in P1 ABS1407.res created by SHELXL-2019/1 at 08:26:24 on 06-Mar-2024 REM Old TITL ABS1407 in P-1 REM SHELXT solution in P1: R1 0.082, Rweak 0.048, Alpha 0.000 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C25 F6 N8 O5 S2 Zn CELL 0.71073 8.4126 8.7175 11.8242 68.674 81.829 82.012 ZERR 1 0.0012 0.0012 0.0016 0.004 0.004 0.004 LATT -1 SFAC C H F N O S Zn UNIT 24 32 6 8 6 2 1 L.S. 10 PLAN 20 SIZE 0.05 0.07 0.09 TEMP -123.15 CONF LIST 4 FMAP 2 53 MORE -1 BOND $H TWIN ACTA WGHT 0.058800 BASF 0.48168 FVAR 0.87136 ZN1 7 0.343189 0.576786 0.389383 11.00000 0.01922 0.02704 = 0.01841 -0.00992 0.00077 -0.00133 S1 6 0.378110 0.201630 0.539392 11.00000 0.02666 0.02453 = 0.02485 -0.00879 -0.00130 0.00130 S2 6 0.935774 0.357140 0.891361 11.00000 0.02001 0.02847 = 0.02263 -0.01226 -0.00156 -0.00165 F1 3 0.486757 0.268954 0.711476 11.00000 0.08298 0.03616 = 0.05221 -0.00808 -0.04001 -0.01084 F2 3 0.542222 0.017125 0.721418 11.00000 0.03979 0.03974 = 0.04267 -0.00833 -0.01295 0.01212 F3 3 0.303501 0.104798 0.776042 11.00000 0.04862 0.05684 = 0.02725 -0.01331 0.00427 0.00209 F4 3 0.961016 0.248386 0.709710 11.00000 0.06006 0.04588 = 0.02380 -0.02077 0.00107 -0.01034 F5 3 0.990143 0.056762 0.884933 11.00000 0.04909 0.02841 = 0.04724 -0.01256 -0.00703 -0.00495 F6 3 0.755929 0.174602 0.840836 11.00000 0.03236 0.05924 = 0.05884 -0.02674 -0.00664 -0.01883 O1 5 0.263715 0.347475 0.524747 11.00000 0.03395 0.02419 = 0.02752 -0.00642 -0.00495 0.00084 O2 5 0.528340 0.242063 0.465438 11.00000 0.03410 0.06363 = 0.02608 -0.00574 0.00163 0.00435 O3 5 0.308143 0.061670 0.540604 11.00000 0.05105 0.02838 = 0.04461 -0.01624 -0.00876 -0.00334 O4 5 0.844272 0.502855 0.816387 11.00000 0.03794 0.03377 = 0.03344 -0.01166 -0.00533 0.00415 O5 5 0.868850 0.289585 1.016908 11.00000 0.03539 0.04563 = 0.02163 -0.01461 -0.00124 -0.00398 O6 5 1.107085 0.365614 0.873986 11.00000 0.02421 0.04141 = 0.03934 -0.02162 -0.00224 -0.00863 N1 4 0.299804 0.475617 0.261958 11.00000 0.01679 0.02981 = 0.02413 -0.01260 0.00204 0.00167 N2 4 0.419014 0.456160 0.174311 11.00000 0.01892 0.02486 = 0.01917 -0.00993 0.00111 0.00138 N3 4 0.523943 0.700770 0.263673 11.00000 0.02445 0.02488 = 0.02045 -0.01265 0.00512 -0.00247 N4 4 0.602350 0.641658 0.174836 11.00000 0.02323 0.02310 = 0.02415 -0.01313 0.00820 -0.00581 N5 4 0.147262 0.749256 0.379801 11.00000 0.02875 0.02204 = 0.01918 -0.00884 -0.00286 0.00427 N6 4 0.081821 0.775337 0.484293 11.00000 0.01522 0.02526 = 0.02728 -0.01252 0.00155 -0.00184 N7 4 0.411447 0.616201 0.538232 11.00000 0.01360 0.02934 = 0.01905 -0.00972 0.00188 -0.00115 N8 4 0.291856 0.660684 0.616133 11.00000 0.01514 0.02588 = 0.01909 -0.01106 0.00336 -0.00284 C1 1 0.165783 0.430337 0.239207 11.00000 0.01888 0.03374 = 0.02350 -0.01232 -0.00036 -0.00010 C2 1 0.198487 0.380306 0.136967 11.00000 0.02494 0.03229 = 0.02564 -0.01178 -0.00693 -0.00254 AFIX 43 H2 2 0.124218 0.342747 0.101645 11.00000 -1.20000 AFIX 0 C3 1 0.359177 0.396645 0.098507 11.00000 0.02536 0.02708 = 0.01989 -0.01135 -0.00432 -0.00032 C4 1 0.009418 0.438286 0.315101 11.00000 0.02246 0.05075 = 0.04165 -0.02087 0.00124 -0.00836 AFIX 137 H4A 2 0.029781 0.442709 0.393380 11.00000 -1.50000 H4B 2 -0.045491 0.339826 0.329550 11.00000 -1.50000 H4C 2 -0.058771 0.537547 0.272237 11.00000 -1.50000 AFIX 0 C5 1 0.461257 0.356194 -0.003320 11.00000 0.03454 0.03717 = 0.02259 -0.01551 0.00198 0.00190 AFIX 137 H5A 2 0.520663 0.450946 -0.053941 11.00000 -1.50000 H5B 2 0.392109 0.331409 -0.053330 11.00000 -1.50000 H5C 2 0.537807 0.259752 0.030670 11.00000 -1.50000 AFIX 0 C6 1 0.582475 0.475482 0.184736 11.00000 0.02015 0.02161 = 0.01934 -0.00757 -0.00107 -0.00095 AFIX 23 H6A 2 0.654511 0.447429 0.119780 11.00000 -1.20000 H6B 2 0.614774 0.397360 0.264426 11.00000 -1.20000 AFIX 0 C7 1 0.570149 0.851751 0.233023 11.00000 0.02962 0.02538 = 0.02526 -0.00945 -0.00111 -0.00168 C8 1 0.677445 0.887958 0.127965 11.00000 0.03886 0.02705 = 0.03451 -0.01152 0.01019 -0.00595 AFIX 43 H8 2 0.728319 0.987168 0.088042 11.00000 -1.20000 AFIX 0 C9 1 0.695274 0.751448 0.093328 11.00000 0.03612 0.02434 = 0.03075 -0.01098 0.01183 -0.01246 C10 1 0.506810 0.964084 0.305582 11.00000 0.04571 0.02612 = 0.03014 -0.01492 0.00554 -0.00853 AFIX 137 H10A 2 0.423252 1.046567 0.263131 11.00000 -1.50000 H10B 2 0.595545 1.020273 0.313454 11.00000 -1.50000 H10C 2 0.460835 0.897763 0.386896 11.00000 -1.50000 AFIX 0 C11 1 0.796759 0.718589 -0.012233 11.00000 0.06662 0.04062 = 0.04880 -0.02647 0.03517 -0.02318 AFIX 137 H11A 2 0.889808 0.639948 0.017559 11.00000 -1.50000 H11B 2 0.834486 0.822407 -0.070735 11.00000 -1.50000 H11C 2 0.732168 0.671981 -0.052365 11.00000 -1.50000 AFIX 0 C12 1 0.086929 0.876472 0.287345 11.00000 0.03074 0.02634 = 0.02611 -0.00634 -0.01245 0.00167 C13 1 -0.018259 0.982386 0.335761 11.00000 0.02712 0.02808 = 0.04896 -0.00978 -0.01257 0.00893 AFIX 43 H13 2 -0.078083 1.081282 0.290621 11.00000 -1.20000 AFIX 0 C14 1 -0.018485 0.916900 0.459407 11.00000 0.01715 0.03021 = 0.04456 -0.01912 -0.00493 0.00299 C15 1 0.135297 0.894045 0.157613 11.00000 0.04350 0.04193 = 0.03386 -0.00532 -0.00788 0.00753 AFIX 137 H15A 2 0.246681 0.923373 0.135118 11.00000 -1.50000 H15B 2 0.063522 0.981200 0.105388 11.00000 -1.50000 H15C 2 0.127566 0.789146 0.146832 11.00000 -1.50000 AFIX 0 C16 1 -0.105042 0.977661 0.556609 11.00000 0.03344 0.04636 = 0.05354 -0.02567 -0.00171 0.00998 AFIX 137 H16A 2 -0.152296 0.885561 0.622992 11.00000 -1.50000 H16B 2 -0.190837 1.063799 0.522301 11.00000 -1.50000 H16C 2 -0.028801 1.023504 0.588330 11.00000 -1.50000 AFIX 0 C17 1 0.126026 0.656916 0.599225 11.00000 0.01855 0.02971 = 0.02503 -0.01188 0.00626 -0.00167 AFIX 23 H17A 2 0.109638 0.544660 0.603323 11.00000 -1.20000 H17B 2 0.054702 0.680581 0.666255 11.00000 -1.20000 AFIX 0 C18 1 0.549751 0.618799 0.580605 11.00000 0.02613 0.02227 = 0.02058 -0.00512 -0.00366 -0.00476 C19 1 0.518024 0.663922 0.684085 11.00000 0.03117 0.02548 = 0.02378 -0.00819 -0.00362 -0.00861 AFIX 43 H19 2 0.595420 0.675416 0.730974 11.00000 -1.20000 AFIX 0 C20 1 0.354400 0.688288 0.704774 11.00000 0.03548 0.01753 = 0.01502 -0.00204 0.00053 -0.00497 C21 1 0.707930 0.574392 0.520362 11.00000 0.01898 0.04104 = 0.04155 -0.01768 -0.00518 -0.00040 AFIX 137 H21A 2 0.698606 0.481862 0.494068 11.00000 -1.50000 H21B 2 0.789824 0.542108 0.578125 11.00000 -1.50000 H21C 2 0.739493 0.669971 0.449234 11.00000 -1.50000 AFIX 0 C22 1 0.250260 0.734387 0.802788 11.00000 0.04226 0.03670 = 0.02984 -0.02008 0.00381 -0.00898 AFIX 137 H22A 2 0.185537 0.839253 0.766175 11.00000 -1.50000 H22B 2 0.318248 0.746591 0.859203 11.00000 -1.50000 H22C 2 0.178566 0.647606 0.847389 11.00000 -1.50000 AFIX 0 C23 1 0.430872 0.146076 0.695887 11.00000 0.03383 0.02657 = 0.02847 -0.00632 -0.00485 -0.00065 C24 1 0.908527 0.200968 0.829065 11.00000 0.02595 0.03311 = 0.02866 -0.01524 -0.00181 -0.00770 HKLF 4 REM abs1407_a.res in P1 REM wR2 = 0.1039, GooF = S = 1.045, Restrained GooF = 1.044 for all data REM R1 = 0.0450 for 3298 Fo > 4sig(Fo) and 0.0644 for all 4035 data REM 433 parameters refined using 3 restraints END WGHT 0.0588 0.0000 REM Highest difference peak 0.543, deepest hole -0.417, 1-sigma level 0.091 Q1 1 0.6402 1.0485 0.0970 11.00000 0.05 0.54 Q2 1 1.0308 0.0863 0.6952 11.00000 0.05 0.48 Q3 1 0.9092 0.2499 0.8804 11.00000 0.05 0.45 Q4 1 0.8261 0.4224 0.8049 11.00000 0.05 0.45 Q5 1 0.3844 0.4902 0.3721 11.00000 0.05 0.44 Q6 1 0.6298 0.8860 0.1890 11.00000 0.05 0.43 Q7 1 0.4001 0.5665 0.3232 11.00000 0.05 0.42 Q8 1 0.3714 0.6990 0.4049 11.00000 0.05 0.39 Q9 1 0.8787 0.4421 0.9007 11.00000 0.05 0.39 Q10 1 0.4626 0.2857 0.4991 11.00000 0.05 0.39 Q11 1 0.5586 0.8885 0.3394 11.00000 0.05 0.38 Q12 1 0.7232 0.4049 0.9395 11.00000 0.05 0.35 Q13 1 0.1587 0.4781 0.1382 11.00000 0.05 0.35 Q14 1 0.9418 0.5572 0.8334 11.00000 0.05 0.34 Q15 1 0.5321 0.6731 0.6347 11.00000 0.05 0.34 Q16 1 0.0981 0.8793 0.4827 11.00000 0.05 0.34 Q17 1 -0.2698 1.1553 0.4537 11.00000 0.05 0.33 Q18 1 0.2641 0.4213 0.1614 11.00000 0.05 0.33 Q19 1 0.2760 0.5855 0.4611 11.00000 0.05 0.33 Q20 1 0.0552 0.9581 0.3767 11.00000 0.05 0.33 ; _shelx_res_checksum 66798 _shelx_hkl_file ; 1 0 0 1870.01 46.20 2 0 0 2375.86 32.80 3 0 0 547.25 20.70 4 0 0 495.85 15.00 5 0 0 1931.71 34.20 6 0 0 75.89 6.30 7 0 0 39.90 9.00 8 0 0 38.20 6.20 9 0 0 1.70 6.30 10 0 0 12.00 16.80 11 0 0 42.60 28.70 -10 1 0 47.10 8.90 -9 1 0 11.90 13.10 -8 1 0 159.38 12.50 -7 1 0 46.00 5.70 -6 1 0 106.89 5.50 -5 1 0 20.60 4.30 -4 1 0 252.07 6.40 -3 1 0 308.87 5.80 -2 1 0 487.55 13.30 -1 1 0 1944.91 23.60 0 1 0 1928.81 42.40 1 1 0 871.71 14.10 2 1 0 6026.90 93.89 3 1 0 50.59 2.10 4 1 0 2170.88 36.10 5 1 0 179.68 16.70 6 1 0 171.88 6.10 7 1 0 142.89 7.00 8 1 0 145.59 16.30 9 1 0 176.28 23.90 10 1 0 97.69 12.50 11 1 0 109.89 17.50 -10 2 0 16.60 13.60 -9 2 0 53.99 17.50 -8 2 0 154.38 8.90 -7 2 0 236.68 14.10 -6 2 0 594.14 22.30 -5 2 0 135.09 5.20 -4 2 0 777.42 16.10 -3 2 0 2043.00 60.19 -2 2 0 1231.88 16.20 -1 2 0 3132.59 36.40 0 2 0 280.47 32.30 1 2 0 1977.10 27.00 2 2 0 1893.41 26.40 3 2 0 519.25 11.90 4 2 0 959.40 25.00 5 2 0 616.24 14.20 6 2 0 153.98 8.10 7 2 0 28.60 17.20 8 2 0 14.00 6.70 9 2 0 62.79 11.20 10 2 0 42.40 18.50 11 2 0 0.00 39.10 -10 3 0 4.50 8.80 -9 3 0 53.19 15.80 -8 3 0 192.98 16.70 -7 3 0 177.08 8.70 -6 3 0 135.59 6.20 -5 3 0 51.39 8.10 -4 3 0 353.26 15.20 -3 3 0 363.36 6.70 -2 3 0 1823.22 39.10 -1 3 0 460.25 14.20 0 3 0 782.22 13.70 1 3 0 793.32 13.20 2 3 0 58.79 16.60 3 3 0 1111.49 20.00 4 3 0 406.26 9.90 5 3 0 687.13 22.20 6 3 0 496.45 16.30 7 3 0 22.50 5.60 8 3 0 118.59 20.90 9 3 0 62.99 19.40 10 3 0 94.79 13.80 11 3 0 18.80 29.20 -9 4 0 67.59 18.70 -8 4 0 155.78 11.90 -7 4 0 123.29 19.90 -6 4 0 5.40 9.20 -5 4 0 245.78 7.60 -4 4 0 329.87 8.00 -3 4 0 651.03 14.10 -2 4 0 29.90 2.20 -1 4 0 650.33 14.30 0 4 0 54.39 3.70 1 4 0 204.38 6.60 2 4 0 475.65 10.80 3 4 0 203.68 9.50 4 4 0 3.40 6.60 5 4 0 40.10 4.20 6 4 0 309.07 12.00 7 4 0 49.00 7.60 8 4 0 359.46 18.50 9 4 0 29.50 10.10 10 4 0 89.49 22.30 -9 5 0 40.70 14.80 -8 5 0 72.19 13.60 -7 5 0 239.38 19.80 -6 5 0 115.79 6.90 -5 5 0 628.54 24.70 -4 5 0 48.50 7.90 -3 5 0 254.67 7.00 -2 5 0 808.22 19.40 -1 5 0 581.34 24.80 0 5 0 156.88 6.40 1 5 0 5.50 1.90 2 5 0 129.59 7.30 3 5 0 444.76 13.10 4 5 0 360.66 11.00 5 5 0 94.69 9.20 6 5 0 144.49 10.90 7 5 0 315.27 12.20 8 5 0 29.50 20.60 9 5 0 75.49 19.20 10 5 0 45.70 13.30 -8 6 0 13.60 9.20 -7 6 0 20.20 17.10 -6 6 0 105.99 12.90 -5 6 0 152.38 8.50 -4 6 0 11.40 4.40 -3 6 0 370.16 14.70 -2 6 0 40.50 5.20 -1 6 0 307.47 9.80 0 6 0 278.77 14.60 1 6 0 106.79 5.60 2 6 0 145.69 6.30 3 6 0 247.38 11.30 4 6 0 45.60 7.90 5 6 0 220.08 10.00 6 6 0 387.66 17.40 7 6 0 277.97 20.00 8 6 0 115.69 21.10 9 6 0 142.29 14.10 -7 7 0 5.90 18.80 -6 7 0 189.98 11.60 -5 7 0 40.50 10.50 -4 7 0 123.49 13.10 -3 7 0 41.40 5.30 -2 7 0 28.70 7.20 -1 7 0 101.39 11.10 0 7 0 86.69 5.30 1 7 0 138.09 7.00 2 7 0 89.39 8.50 3 7 0 193.08 11.50 4 7 0 1.70 5.80 5 7 0 0.00 14.80 6 7 0 110.19 17.80 7 7 0 101.59 10.10 8 7 0 54.29 22.40 9 7 0 39.00 28.90 -6 8 0 86.49 13.60 -5 8 0 33.60 9.00 -4 8 0 42.90 7.30 -3 8 0 60.69 12.60 -2 8 0 369.26 23.70 -1 8 0 126.89 8.50 0 8 0 103.79 10.90 1 8 0 116.69 12.80 2 8 0 218.18 10.90 3 8 0 355.06 21.20 4 8 0 9.60 10.30 5 8 0 128.49 12.20 6 8 0 52.79 10.50 7 8 0 0.00 27.10 8 8 0 0.00 26.50 -5 9 0 89.89 16.10 -4 9 0 9.00 12.40 -3 9 0 15.30 6.90 -2 9 0 48.00 10.60 -1 9 0 77.49 14.40 0 9 0 34.10 8.90 1 9 0 15.60 6.40 2 9 0 39.20 14.70 3 9 0 117.39 20.30 4 9 0 21.20 8.60 5 9 0 1.40 16.10 6 9 0 18.30 19.00 7 9 0 48.40 17.40 -3 10 0 103.79 15.10 -2 10 0 41.00 17.50 -1 10 0 65.59 10.30 0 10 0 160.08 20.50 1 10 0 24.10 13.70 2 10 0 37.90 9.80 3 10 0 8.40 10.00 4 10 0 35.20 15.90 5 10 0 45.20 34.70 -4 -10 1 30.10 23.30 -3 -10 1 84.99 15.80 -2 -10 1 3.40 12.40 -1 -10 1 44.70 10.30 0 -10 1 35.90 14.80 1 -10 1 60.99 18.40 2 -10 1 97.09 10.40 -6 -9 1 17.30 11.30 -5 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558.14 12.20 7 3 2 185.88 13.90 8 3 2 146.69 22.90 9 3 2 6.30 8.10 10 3 2 17.40 21.40 11 3 2 154.88 32.80 -9 4 2 29.10 9.20 -8 4 2 45.60 12.10 -7 4 2 120.49 17.80 -6 4 2 79.09 5.70 -5 4 2 45.20 10.80 -4 4 2 930.01 32.00 -3 4 2 290.07 7.30 -2 4 2 495.75 9.00 -1 4 2 208.88 12.60 0 4 2 835.72 14.50 1 4 2 688.63 11.70 2 4 2 51.89 4.30 3 4 2 1085.39 21.30 4 4 2 1215.18 22.20 5 4 2 883.61 22.00 6 4 2 133.39 14.50 7 4 2 314.37 10.70 8 4 2 190.08 18.70 9 4 2 35.90 14.90 10 4 2 76.39 14.40 11 4 2 28.80 19.30 -9 5 2 48.10 16.90 -8 5 2 94.69 11.10 -7 5 2 63.79 11.00 -6 5 2 234.38 15.90 -5 5 2 175.68 8.40 -4 5 2 16.20 3.40 -3 5 2 525.15 15.40 -2 5 2 1.90 2.50 -1 5 2 163.98 4.60 0 5 2 1261.87 29.40 1 5 2 24.20 2.80 2 5 2 13.00 1.50 3 5 2 6.30 2.70 4 5 2 90.79 20.10 5 5 2 671.43 15.00 6 5 2 117.99 5.80 7 5 2 116.39 13.20 8 5 2 44.00 19.10 9 5 2 38.70 9.60 10 5 2 58.79 25.60 -8 6 2 14.30 15.70 -7 6 2 18.30 16.40 -6 6 2 458.65 17.00 -5 6 2 112.59 15.00 -4 6 2 107.29 10.50 -3 6 2 498.15 12.70 -2 6 2 70.69 5.20 -1 6 2 1760.32 41.00 0 6 2 392.56 9.90 1 6 2 577.84 11.90 2 6 2 583.44 20.20 3 6 2 148.69 8.60 4 6 2 438.76 11.50 5 6 2 67.99 9.60 6 6 2 41.50 12.50 7 6 2 47.10 6.60 8 6 2 36.70 10.90 9 6 2 55.59 19.10 10 6 2 14.60 22.00 -8 7 2 9.80 19.50 -7 7 2 153.48 15.10 -6 7 2 36.90 14.00 -5 7 2 0.00 13.10 -4 7 2 238.48 10.90 -3 7 2 16.70 10.10 -2 7 2 391.46 16.40 -1 7 2 246.68 9.50 0 7 2 82.29 6.40 1 7 2 675.23 29.90 2 7 2 184.08 7.30 3 7 2 125.19 8.10 4 7 2 289.77 17.40 5 7 2 104.89 24.60 6 7 2 112.19 9.50 7 7 2 139.09 17.80 8 7 2 67.79 19.40 9 7 2 48.10 11.40 -7 8 2 69.99 23.60 -6 8 2 21.20 8.00 -5 8 2 67.29 12.90 -4 8 2 200.98 12.90 -3 8 2 164.88 9.90 -2 8 2 89.09 8.40 -1 8 2 74.69 17.30 0 8 2 329.97 17.30 1 8 2 69.39 6.40 2 8 2 65.79 10.10 3 8 2 187.18 17.40 4 8 2 2.90 5.40 5 8 2 126.79 14.80 6 8 2 162.18 16.20 7 8 2 2.70 9.40 8 8 2 65.09 13.00 -5 9 2 0.00 14.70 -4 9 2 57.39 8.20 -3 9 2 64.59 13.20 -2 9 2 53.19 13.70 -1 9 2 50.59 9.60 0 9 2 87.19 10.90 1 9 2 97.89 10.20 2 9 2 161.78 11.10 3 9 2 109.09 8.30 4 9 2 82.79 13.40 5 9 2 168.78 17.30 6 9 2 39.70 9.50 7 9 2 21.10 21.90 -4 10 2 47.90 17.00 -3 10 2 24.80 15.30 -2 10 2 8.20 7.90 -1 10 2 0.00 14.30 0 10 2 26.50 15.20 1 10 2 9.20 7.00 2 10 2 48.50 14.80 3 10 2 24.70 13.20 4 10 2 15.20 9.20 5 10 2 193.28 21.20 6 10 2 23.40 16.00 -1 11 2 24.30 9.70 0 11 2 13.20 10.50 1 11 2 4.50 12.70 2 11 2 0.00 23.70 3 11 2 26.00 12.80 -5 -9 3 15.30 18.00 -4 -9 3 6.50 10.70 -3 -9 3 11.10 15.50 -2 -9 3 105.69 21.60 -1 -9 3 85.39 11.70 0 -9 3 37.70 20.80 1 -9 3 97.79 15.70 2 -9 3 33.30 8.10 3 -9 3 35.60 11.00 -6 -8 3 81.59 16.60 -5 -8 3 6.00 20.70 -4 -8 3 117.39 20.50 -3 -8 3 9.60 9.10 -2 -8 3 190.38 12.90 -1 -8 3 47.30 12.60 0 -8 3 16.50 10.20 1 -8 3 21.10 6.70 2 -8 3 9.20 10.00 3 -8 3 23.20 12.30 4 -8 3 23.40 7.10 5 -8 3 2.90 22.00 -7 -7 3 45.10 11.00 -6 -7 3 1.40 16.50 -5 -7 3 81.59 14.90 -4 -7 3 88.79 9.10 -3 -7 3 210.48 16.70 -2 -7 3 228.08 13.60 -1 -7 3 188.28 11.30 0 -7 3 789.12 29.00 1 -7 3 79.09 13.80 2 -7 3 214.68 11.10 3 -7 3 121.49 7.60 4 -7 3 24.90 8.70 5 -7 3 64.39 16.00 6 -7 3 15.90 7.60 7 -7 3 25.10 58.59 -8 -6 3 18.30 24.70 -7 -6 3 0.00 19.50 -6 -6 3 73.39 7.90 -5 -6 3 29.80 8.20 -4 -6 3 52.49 10.30 -3 -6 3 116.49 7.50 -2 -6 3 32.90 4.80 -1 -6 3 232.48 11.80 0 -6 3 166.58 8.80 1 -6 3 82.79 7.30 2 -6 3 119.29 12.90 3 -6 3 74.29 9.80 4 -6 3 199.38 9.00 5 -6 3 95.79 15.10 6 -6 3 0.00 11.20 7 -6 3 82.29 11.60 8 -6 3 62.59 31.80 -9 -5 3 41.10 16.20 -8 -5 3 46.90 12.20 -7 -5 3 42.00 7.20 -6 -5 3 237.18 13.10 -5 -5 3 84.39 10.00 -4 -5 3 426.46 12.50 -3 -5 3 266.87 16.40 -2 -5 3 28.70 8.40 -1 -5 3 214.58 7.50 0 -5 3 209.98 7.30 1 -5 3 832.12 25.90 2 -5 3 122.59 6.60 3 -5 3 87.09 5.40 4 -5 3 105.09 7.70 5 -5 3 38.10 8.00 6 -5 3 6.20 4.50 7 -5 3 70.29 16.60 8 -5 3 5.60 17.20 -9 -4 3 29.50 8.50 -8 -4 3 73.59 15.90 -7 -4 3 238.98 14.70 -6 -4 3 52.09 6.10 -5 -4 3 30.90 5.00 -4 -4 3 214.68 13.00 -3 -4 3 149.99 6.00 -2 -4 3 465.85 12.00 -1 -4 3 277.37 10.70 0 -4 3 527.15 17.70 1 -4 3 733.53 15.80 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13.40 8 -4 4 0.00 10.40 9 -4 4 34.60 10.70 -9 -3 4 23.80 8.50 -8 -3 4 84.89 12.50 -7 -3 4 127.69 11.00 -6 -3 4 246.38 11.40 -5 -3 4 56.79 12.30 -4 -3 4 75.59 7.70 -3 -3 4 73.99 4.50 -2 -3 4 422.06 12.80 -1 -3 4 723.23 32.60 0 -3 4 115.99 4.20 1 -3 4 141.29 4.80 2 -3 4 579.94 14.40 3 -3 4 272.07 8.00 4 -3 4 1256.27 25.00 5 -3 4 304.27 11.70 6 -3 4 358.06 16.40 7 -3 4 370.96 12.40 8 -3 4 0.20 14.60 9 -3 4 87.19 14.10 -10 -2 4 61.19 18.80 -9 -2 4 190.28 17.90 -8 -2 4 299.07 14.70 -7 -2 4 496.15 19.30 -6 -2 4 756.92 24.30 -5 -2 4 42.70 4.30 -4 -2 4 979.80 20.00 -3 -2 4 220.28 9.70 -2 -2 4 333.57 9.70 -1 -2 4 196.88 6.20 0 -2 4 240.68 11.10 1 -2 4 62.39 5.50 2 -2 4 419.46 9.10 3 -2 4 65.49 3.70 4 -2 4 188.48 11.30 5 -2 4 111.39 5.10 6 -2 4 52.79 4.40 7 -2 4 0.00 8.60 8 -2 4 214.58 21.60 9 -2 4 23.10 7.20 10 -2 4 60.29 23.90 -10 -1 4 24.10 13.50 -9 -1 4 79.59 11.30 -8 -1 4 24.90 15.30 -7 -1 4 555.54 27.70 -6 -1 4 479.05 14.70 -5 -1 4 580.14 17.30 -4 -1 4 1634.74 37.40 -3 -1 4 583.34 11.10 -2 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190.78 10.50 -1 4 11 442.86 13.70 0 4 11 20.00 3.50 1 4 11 109.99 10.40 2 4 11 231.78 12.40 3 4 11 363.86 12.80 4 4 11 426.16 19.60 5 4 11 58.59 10.90 6 4 11 19.30 6.40 7 4 11 29.40 13.00 8 4 11 46.30 14.80 9 4 11 18.20 15.90 -6 5 11 21.90 16.20 -5 5 11 31.20 8.80 -4 5 11 40.00 13.80 -3 5 11 152.58 15.20 -2 5 11 112.29 7.30 -1 5 11 467.35 20.00 0 5 11 200.08 16.60 1 5 11 516.35 14.30 2 5 11 216.88 9.10 3 5 11 259.57 13.80 4 5 11 460.45 21.80 5 5 11 204.38 12.30 6 5 11 87.99 14.60 7 5 11 96.29 17.60 8 5 11 85.79 11.70 9 5 11 20.80 20.60 -5 6 11 38.60 17.00 -4 6 11 58.09 9.10 -3 6 11 8.50 5.10 -2 6 11 86.09 9.30 -1 6 11 62.99 9.90 0 6 11 119.09 6.90 1 6 11 172.18 14.10 2 6 11 0.00 8.50 3 6 11 219.68 10.80 4 6 11 140.39 16.80 5 6 11 32.00 12.20 6 6 11 7.40 6.50 7 6 11 7.80 7.80 8 6 11 79.09 14.50 -5 7 11 112.59 12.20 -4 7 11 96.09 19.70 -3 7 11 223.98 17.30 -2 7 11 235.58 9.70 -1 7 11 182.98 15.50 0 7 11 504.75 17.30 1 7 11 129.69 9.80 2 7 11 147.89 8.80 3 7 11 179.98 11.30 4 7 11 63.29 11.80 5 7 11 60.99 7.90 6 7 11 16.80 13.40 7 7 11 82.49 15.50 8 7 11 17.90 8.60 -4 8 11 3.10 10.50 -3 8 11 10.50 6.90 -2 8 11 82.69 15.90 -1 8 11 63.29 22.60 0 8 11 95.19 9.20 1 8 11 28.80 15.60 2 8 11 100.39 12.50 3 8 11 3.80 5.30 4 8 11 63.39 11.00 5 8 11 22.90 11.40 6 8 11 46.50 9.30 7 8 11 110.99 11.50 -3 9 11 98.19 19.90 -2 9 11 85.89 10.30 -1 9 11 59.49 15.30 0 9 11 3.80 12.40 1 9 11 99.89 14.40 2 9 11 108.79 11.10 3 9 11 27.80 13.40 4 9 11 0.00 15.90 5 9 11 10.00 7.80 6 9 11 20.50 24.70 -1 10 11 22.80 16.50 0 10 11 104.19 13.10 1 10 11 97.89 21.20 2 10 11 0.00 16.40 3 10 11 66.39 11.20 4 10 11 48.10 11.70 5 10 11 33.30 27.10 -2 -3 12 30.50 10.40 -1 -3 12 109.99 10.70 0 -3 12 21.30 14.30 1 -3 12 158.98 17.90 2 -3 12 93.09 10.90 3 -3 12 45.60 21.20 4 -3 12 119.09 34.80 -4 -2 12 45.30 39.60 -3 -2 12 27.10 8.10 -2 -2 12 14.70 13.90 -1 -2 12 91.19 15.30 0 -2 12 17.80 6.80 1 -2 12 48.70 16.20 2 -2 12 68.69 13.60 3 -2 12 97.29 12.40 4 -2 12 108.59 11.60 5 -2 12 0.00 14.20 -5 -1 12 43.90 19.10 -4 -1 12 71.09 16.70 -3 -1 12 25.80 11.30 -2 -1 12 271.77 16.20 -1 -1 12 39.50 7.20 0 -1 12 68.69 12.80 1 -1 12 49.50 14.20 2 -1 12 13.60 7.00 3 -1 12 90.09 16.00 4 -1 12 17.60 14.50 5 -1 12 35.50 8.70 6 -1 12 17.00 9.50 -5 0 12 93.69 17.20 -4 0 12 0.60 14.70 -3 0 12 37.00 7.40 -2 0 12 149.88 15.10 -1 0 12 25.80 10.20 0 0 12 176.08 10.40 1 0 12 241.18 13.50 2 0 12 51.19 10.70 3 0 12 124.89 11.80 4 0 12 10.20 6.80 5 0 12 81.89 15.00 6 0 12 52.09 16.50 7 0 12 136.29 13.60 -5 1 12 37.90 10.10 -4 1 12 14.50 8.50 -3 1 12 105.49 11.20 -2 1 12 131.79 12.30 -1 1 12 176.88 10.20 0 1 12 12.00 12.40 1 1 12 20.20 11.60 2 1 12 213.88 11.50 3 1 12 13.70 12.40 4 1 12 146.39 13.70 5 1 12 18.40 6.80 6 1 12 13.30 9.00 7 1 12 174.08 16.30 -5 2 12 120.89 21.30 -4 2 12 104.69 19.30 -3 2 12 107.79 8.70 -2 2 12 225.28 17.50 -1 2 12 277.37 16.10 0 2 12 119.39 8.00 1 2 12 400.26 14.20 2 2 12 408.66 18.80 3 2 12 140.99 14.30 4 2 12 124.79 8.60 5 2 12 11.90 11.90 6 2 12 186.78 14.20 7 2 12 6.60 6.70 8 2 12 48.20 9.60 -5 3 12 70.39 15.90 -4 3 12 62.09 10.90 -3 3 12 0.00 12.90 -2 3 12 112.99 16.30 -1 3 12 149.19 8.60 0 3 12 134.19 11.70 1 3 12 265.97 14.00 2 3 12 163.58 9.00 3 3 12 222.98 16.60 4 3 12 146.99 12.50 5 3 12 68.49 8.90 6 3 12 180.68 10.80 7 3 12 56.89 15.80 8 3 12 135.89 22.10 -5 4 12 107.79 27.70 -4 4 12 240.98 22.10 -3 4 12 118.79 9.90 -2 4 12 145.39 11.30 -1 4 12 97.19 12.50 0 4 12 180.18 9.50 1 4 12 75.99 6.30 2 4 12 49.00 8.80 3 4 12 273.27 15.50 4 4 12 9.50 5.10 5 4 12 0.00 15.70 6 4 12 4.60 14.10 7 4 12 20.00 8.70 8 4 12 95.39 14.30 -5 5 12 7.90 16.30 -4 5 12 29.80 7.90 -3 5 12 20.70 16.70 -2 5 12 286.07 17.60 -1 5 12 150.18 8.10 0 5 12 264.47 17.40 1 5 12 100.89 14.60 2 5 12 132.89 8.30 3 5 12 62.19 9.10 4 5 12 323.97 17.20 5 5 12 245.48 17.10 6 5 12 23.90 8.40 7 5 12 181.28 18.80 8 5 12 26.60 21.50 -5 6 12 0.90 31.50 -4 6 12 31.20 13.10 -3 6 12 51.89 7.00 -2 6 12 4.50 5.20 -1 6 12 100.19 9.50 0 6 12 254.07 15.10 1 6 12 41.60 5.80 2 6 12 96.59 15.60 3 6 12 63.79 13.80 4 6 12 34.50 7.40 5 6 12 62.29 16.20 6 6 12 4.60 13.70 7 6 12 29.40 9.60 8 6 12 12.40 9.90 -4 7 12 75.99 8.90 -3 7 12 79.59 16.40 -2 7 12 68.29 13.80 -1 7 12 72.69 6.60 0 7 12 18.80 17.50 1 7 12 478.95 21.50 2 7 12 29.90 8.30 3 7 12 84.99 8.40 4 7 12 130.79 13.00 5 7 12 115.29 15.80 6 7 12 88.99 9.50 7 7 12 54.19 16.00 -3 8 12 56.29 16.80 -2 8 12 62.89 10.00 -1 8 12 32.30 13.10 0 8 12 106.89 34.20 1 8 12 212.48 11.90 2 8 12 0.00 12.60 3 8 12 156.08 15.40 4 8 12 32.50 7.30 5 8 12 125.49 19.50 6 8 12 63.59 12.90 7 8 12 15.30 21.10 -2 9 12 8.70 16.30 -1 9 12 80.59 9.70 0 9 12 56.89 17.40 1 9 12 0.00 11.60 2 9 12 33.30 13.00 3 9 12 43.00 9.80 4 9 12 28.80 15.80 5 9 12 74.69 20.60 6 9 12 0.00 17.50 0 10 12 20.10 36.30 1 10 12 43.40 11.40 2 10 12 29.20 19.80 3 10 12 51.49 19.10 4 10 12 19.20 56.59 -2 -2 13 71.49 14.90 -1 -2 13 1.60 22.20 0 -2 13 60.59 16.80 1 -2 13 31.30 8.10 2 -2 13 109.09 18.70 3 -2 13 137.89 20.80 -3 -1 13 95.29 13.50 -2 -1 13 25.20 11.90 -1 -1 13 115.69 12.40 0 -1 13 3.30 6.40 1 -1 13 34.20 13.10 2 -1 13 17.30 16.40 3 -1 13 1.90 7.50 4 -1 13 26.70 17.00 5 -1 13 12.90 18.80 -4 0 13 75.49 17.00 -3 0 13 46.70 15.20 -2 0 13 145.49 11.00 -1 0 13 370.06 21.90 0 0 13 209.08 16.60 1 0 13 228.68 12.60 2 0 13 31.50 11.60 3 0 13 167.38 14.20 4 0 13 94.79 13.10 5 0 13 20.70 8.40 6 0 13 72.19 12.40 -4 1 13 48.30 11.20 -3 1 13 5.50 8.20 -2 1 13 29.40 9.90 -1 1 13 33.70 11.30 0 1 13 13.80 6.10 1 1 13 85.99 15.20 2 1 13 0.00 12.80 3 1 13 145.19 10.60 4 1 13 31.80 14.80 5 1 13 17.20 14.20 6 1 13 132.29 12.50 7 1 13 0.00 87.19 -4 2 13 111.89 17.00 -3 2 13 91.29 15.20 -2 2 13 231.28 12.60 -1 2 13 206.18 17.30 0 2 13 173.38 15.40 1 2 13 83.19 8.90 2 2 13 192.78 11.50 3 2 13 255.57 15.30 4 2 13 87.29 15.20 5 2 13 39.40 7.80 6 2 13 22.70 15.00 7 2 13 0.00 18.30 -4 3 13 9.30 12.70 -3 3 13 22.20 7.80 -2 3 13 39.30 12.70 -1 3 13 101.09 16.40 0 3 13 168.78 9.50 1 3 13 129.89 13.60 2 3 13 180.78 15.20 3 3 13 153.68 10.30 4 3 13 12.00 14.00 5 3 13 98.09 12.10 6 3 13 54.89 9.70 7 3 13 120.89 11.60 -4 4 13 69.09 18.20 -3 4 13 112.19 17.30 -2 4 13 39.30 7.60 -1 4 13 43.00 12.40 0 4 13 78.89 13.40 1 4 13 71.49 8.40 2 4 13 33.80 6.00 3 4 13 14.30 9.60 4 4 13 43.80 13.30 5 4 13 80.89 8.50 6 4 13 14.80 17.40 7 4 13 101.49 18.50 -4 5 13 73.49 16.80 -3 5 13 76.29 9.40 -2 5 13 59.49 18.50 -1 5 13 61.49 16.80 0 5 13 10.20 5.80 1 5 13 267.17 18.00 2 5 13 67.79 10.40 3 5 13 143.39 9.20 4 5 13 110.09 12.30 5 5 13 7.40 11.70 6 5 13 58.59 16.20 7 5 13 10.60 9.40 -4 6 13 93.89 16.40 -3 6 13 5.20 15.40 -2 6 13 69.79 8.10 -1 6 13 8.40 6.10 0 6 13 49.60 10.20 1 6 13 244.78 20.30 2 6 13 7.80 7.40 3 6 13 115.09 17.10 4 6 13 124.89 16.40 5 6 13 288.27 18.90 6 6 13 219.18 21.70 7 6 13 7.40 15.70 -3 7 13 75.99 9.00 -2 7 13 131.39 19.20 -1 7 13 116.79 21.70 0 7 13 126.29 9.30 1 7 13 27.50 18.40 2 7 13 154.88 15.00 3 7 13 26.00 9.40 4 7 13 22.30 7.40 5 7 13 57.39 13.20 6 7 13 20.20 16.20 7 7 13 34.60 21.00 -2 8 13 92.89 14.50 -1 8 13 115.39 13.20 0 8 13 124.29 16.10 1 8 13 156.78 29.80 2 8 13 127.69 11.50 3 8 13 2.10 15.50 4 8 13 83.49 16.90 5 8 13 11.30 7.50 6 8 13 148.29 17.90 0 9 13 10.50 10.50 1 9 13 6.00 16.70 2 9 13 44.70 19.80 3 9 13 27.60 20.90 4 9 13 2.80 9.80 5 9 13 18.90 18.70 -1 -1 14 5.50 144.69 0 -1 14 61.79 14.90 1 -1 14 15.70 8.70 2 -1 14 22.70 12.10 3 -1 14 35.00 47.30 -2 0 14 104.69 22.10 -1 0 14 75.19 9.60 0 0 14 289.97 22.50 1 0 14 31.70 14.50 2 0 14 72.89 10.60 3 0 14 61.99 11.90 4 0 14 48.70 14.60 -3 1 14 8.50 17.80 -2 1 14 19.70 9.10 -1 1 14 78.49 12.40 0 1 14 131.29 16.60 1 1 14 19.80 7.00 2 1 14 66.89 15.60 3 1 14 52.79 15.00 4 1 14 91.29 10.60 5 1 14 46.50 9.50 -3 2 14 95.39 17.50 -2 2 14 51.89 17.20 -1 2 14 59.99 7.80 0 2 14 23.40 14.20 1 2 14 60.39 11.90 2 2 14 38.30 9.20 3 2 14 14.90 8.10 4 2 14 38.50 11.80 5 2 14 0.00 16.00 6 2 14 22.70 14.70 -3 3 14 9.70 12.50 -2 3 14 49.30 8.80 -1 3 14 90.79 14.60 0 3 14 84.69 15.90 1 3 14 231.18 12.30 2 3 14 111.69 14.30 3 3 14 98.79 13.60 4 3 14 64.99 8.70 5 3 14 30.80 16.20 6 3 14 39.70 18.70 -3 4 14 86.09 20.70 -2 4 14 60.99 16.00 -1 4 14 15.40 6.80 0 4 14 14.00 12.70 1 4 14 70.19 12.10 2 4 14 6.60 7.60 3 4 14 89.29 8.80 4 4 14 88.39 17.20 5 4 14 86.49 20.80 6 4 14 42.30 9.10 -3 5 14 277.17 21.60 -2 5 14 127.69 11.10 -1 5 14 30.60 16.80 0 5 14 81.99 17.90 1 5 14 23.20 7.00 2 5 14 76.89 22.60 3 5 14 17.70 12.80 4 5 14 30.70 8.10 5 5 14 42.40 14.30 6 5 14 9.60 13.80 -3 6 14 98.89 19.90 -2 6 14 77.79 20.40 -1 6 14 115.39 10.00 0 6 14 81.39 14.40 1 6 14 17.50 12.50 2 6 14 167.68 19.10 3 6 14 6.30 8.30 4 6 14 43.80 15.10 5 6 14 20.30 18.10 6 6 14 130.49 14.60 -2 7 14 47.90 12.20 -1 7 14 83.09 22.50 0 7 14 3.70 20.60 1 7 14 84.39 10.70 2 7 14 29.20 17.60 3 7 14 28.90 12.20 4 7 14 31.50 10.10 5 7 14 6.50 7.60 0 8 14 89.49 13.20 1 8 14 51.09 21.80 2 8 14 40.20 19.90 3 8 14 58.49 9.70 4 8 14 4.80 8.80 0 1 15 62.19 18.20 1 1 15 92.39 17.60 2 1 15 14.20 8.30 3 1 15 30.90 14.80 -1 2 15 4.70 19.20 0 2 15 29.10 7.40 1 2 15 45.90 15.50 2 2 15 0.00 12.10 3 2 15 25.10 10.00 4 2 15 3.70 11.20 -2 3 15 0.00 48.30 -1 3 15 33.00 8.80 0 3 15 54.49 13.90 1 3 15 72.09 16.90 2 3 15 55.79 8.40 3 3 15 31.90 14.20 4 3 15 9.40 15.00 -2 4 15 38.70 16.50 -1 4 15 126.79 17.60 0 4 15 21.00 8.00 1 4 15 84.79 16.30 2 4 15 158.58 15.00 3 4 15 6.30 8.90 4 4 15 56.59 10.30 5 4 15 37.80 18.60 -1 5 15 12.70 8.40 0 5 15 68.69 17.80 1 5 15 29.30 16.30 2 5 15 16.50 8.40 3 5 15 11.50 23.70 4 5 15 11.50 16.80 5 5 15 10.20 16.80 -1 6 15 153.18 24.50 0 6 15 193.98 19.70 1 6 15 66.89 17.00 2 6 15 24.80 15.80 3 6 15 68.59 19.00 4 6 15 11.70 9.80 0 7 15 35.30 16.00 1 7 15 54.69 33.90 2 7 15 16.00 8.70 3 7 15 59.29 12.50 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' ; _shelx_hkl_checksum 45688 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 Zn1 Zn 0.34319(5) 0.57679(5) 0.38938(5) 0.02137(15) Uani 1 1 d . . . . . S1 S 0.37811(16) 0.20163(15) 0.53939(12) 0.0258(3) Uani 1 1 d . . . . . S2 S 0.93577(15) 0.35714(15) 0.89136(12) 0.0229(3) Uani 1 1 d . . . . . F1 F 0.4868(6) 0.2690(5) 0.7115(4) 0.0552(11) Uani 1 1 d . . . . . F2 F 0.5422(4) 0.0171(4) 0.7214(3) 0.0432(9) Uani 1 1 d . . . . . F3 F 0.3035(5) 0.1048(5) 0.7760(3) 0.0462(9) Uani 1 1 d . . . . . F4 F 0.9610(5) 0.2484(4) 0.7097(3) 0.0408(9) Uani 1 1 d . . . . . F5 F 0.9901(5) 0.0568(4) 0.8849(3) 0.0414(8) Uani 1 1 d . . . . . F6 F 0.7559(4) 0.1746(5) 0.8408(4) 0.0468(9) Uani 1 1 d . . . . . O1 O 0.2637(5) 0.3475(4) 0.5247(3) 0.0295(8) Uani 1 1 d . . . . . O2 O 0.5283(5) 0.2421(6) 0.4654(4) 0.0455(11) Uani 1 1 d . . . . . O3 O 0.3081(6) 0.0617(5) 0.5406(4) 0.0400(10) Uani 1 1 d . . . . . O4 O 0.8443(5) 0.5029(5) 0.8164(4) 0.0357(9) Uani 1 1 d . . . . . O5 O 0.8689(5) 0.2896(5) 1.0169(3) 0.0336(9) Uani 1 1 d . . . . . O6 O 1.1071(5) 0.3656(5) 0.8740(4) 0.0324(9) Uani 1 1 d . . . . . N1 N 0.2998(5) 0.4756(6) 0.2620(4) 0.0235(9) Uani 1 1 d . . . . . N2 N 0.4190(5) 0.4562(5) 0.1743(4) 0.0210(9) Uani 1 1 d . . . . . N3 N 0.5239(5) 0.7008(5) 0.2637(4) 0.0227(9) Uani 1 1 d . . . . . N4 N 0.6023(5) 0.6417(5) 0.1748(4) 0.0229(9) Uani 1 1 d . . . . . N5 N 0.1473(5) 0.7493(5) 0.3798(4) 0.0235(9) Uani 1 1 d . . . . . N6 N 0.0818(5) 0.7753(5) 0.4843(4) 0.0220(9) Uani 1 1 d . . . . . N7 N 0.4114(5) 0.6162(5) 0.5382(4) 0.0208(9) Uani 1 1 d . . . . . N8 N 0.2919(5) 0.6607(6) 0.6161(4) 0.0196(9) Uani 1 1 d . . . . . C1 C 0.1658(6) 0.4303(7) 0.2392(5) 0.0252(11) Uani 1 1 d . . . . . C2 C 0.1985(6) 0.3803(7) 0.1370(5) 0.0267(11) Uani 1 1 d . . . . . H2 H 0.124218 0.342747 0.101645 0.032 Uiso 1 1 calc R U . . . C3 C 0.3592(6) 0.3966(6) 0.0985(4) 0.0232(11) Uani 1 1 d . . . . . C4 C 0.0094(7) 0.4383(8) 0.3151(6) 0.0369(13) Uani 1 1 d . . . . . H4A H 0.029781 0.442709 0.393380 0.055 Uiso 1 1 calc R U . . . H4B H -0.045491 0.339826 0.329550 0.055 Uiso 1 1 calc R U . . . H4C H -0.058771 0.537547 0.272237 0.055 Uiso 1 1 calc R U . . . C5 C 0.4613(7) 0.3562(7) -0.0033(5) 0.0311(13) Uani 1 1 d . . . . . H5A H 0.520663 0.450946 -0.053941 0.047 Uiso 1 1 calc R U . . . H5B H 0.392109 0.331409 -0.053330 0.047 Uiso 1 1 calc R U . . . H5C H 0.537807 0.259752 0.030670 0.047 Uiso 1 1 calc R U . . . C6 C 0.5825(6) 0.4755(6) 0.1847(5) 0.0205(10) Uani 1 1 d . . . . . H6A H 0.654511 0.447429 0.119780 0.025 Uiso 1 1 calc R U . . . H6B H 0.614774 0.397360 0.264426 0.025 Uiso 1 1 calc R U . . . C7 C 0.5701(7) 0.8518(7) 0.2330(5) 0.0269(11) Uani 1 1 d . . . . . C8 C 0.6774(7) 0.8880(7) 0.1280(5) 0.0344(13) Uani 1 1 d . . . . . H8 H 0.728319 0.987168 0.088042 0.041 Uiso 1 1 calc R U . . . C9 C 0.6953(7) 0.7514(7) 0.0933(5) 0.0306(12) Uani 1 1 d . . . . . C10 C 0.5068(8) 0.9641(7) 0.3056(5) 0.0330(13) Uani 1 1 d . . . . . H10A H 0.423252 1.046567 0.263131 0.050 Uiso 1 1 calc R U . . . H10B H 0.595545 1.020273 0.313454 0.050 Uiso 1 1 calc R U . . . H10C H 0.460835 0.897763 0.386896 0.050 Uiso 1 1 calc R U . . . C11 C 0.7968(9) 0.7186(8) -0.0122(6) 0.051(2) Uani 1 1 d . . . . . H11A H 0.889808 0.639948 0.017559 0.077 Uiso 1 1 calc R U . . . H11B H 0.834486 0.822407 -0.070735 0.077 Uiso 1 1 calc R U . . . H11C H 0.732168 0.671981 -0.052365 0.077 Uiso 1 1 calc R U . . . C12 C 0.0869(7) 0.8765(7) 0.2873(5) 0.0280(11) Uani 1 1 d . . . . . C13 C -0.0183(7) 0.9824(7) 0.3358(6) 0.0360(14) Uani 1 1 d . . . . . H13 H -0.078083 1.081282 0.290621 0.043 Uiso 1 1 calc R U . . . C14 C -0.0185(6) 0.9169(7) 0.4594(6) 0.0293(12) Uani 1 1 d . . . . . C15 C 0.1353(8) 0.8940(8) 0.1576(6) 0.0428(15) Uani 1 1 d . . . . . H15A H 0.246681 0.923373 0.135118 0.064 Uiso 1 1 calc R U . . . H15B H 0.063522 0.981200 0.105388 0.064 Uiso 1 1 calc R U . . . H15C H 0.127566 0.789146 0.146832 0.064 Uiso 1 1 calc R U . . . C16 C -0.1050(8) 0.9777(9) 0.5566(6) 0.0438(15) Uani 1 1 d . . . . . H16A H -0.152296 0.885561 0.622992 0.066 Uiso 1 1 calc R U . . . H16B H -0.190837 1.063799 0.522301 0.066 Uiso 1 1 calc R U . . . H16C H -0.028801 1.023504 0.588330 0.066 Uiso 1 1 calc R U . . . C17 C 0.1260(6) 0.6569(7) 0.5992(5) 0.0247(11) Uani 1 1 d . . . . . H17A H 0.109638 0.544660 0.603323 0.030 Uiso 1 1 calc R U . . . H17B H 0.054702 0.680581 0.666255 0.030 Uiso 1 1 calc R U . . . C18 C 0.5498(6) 0.6188(6) 0.5806(4) 0.0233(10) Uani 1 1 d . . . . . C19 C 0.5180(7) 0.6639(6) 0.6841(5) 0.0262(11) Uani 1 1 d . . . . . H19 H 0.595420 0.675416 0.730974 0.031 Uiso 1 1 calc R U . . . C20 C 0.3544(7) 0.6883(6) 0.7048(4) 0.0238(11) Uani 1 1 d . . . . . C21 C 0.7079(6) 0.5744(8) 0.5204(6) 0.0330(13) Uani 1 1 d . . . . . H21A H 0.698606 0.481862 0.494068 0.049 Uiso 1 1 calc R U . . . H21B H 0.789824 0.542108 0.578125 0.049 Uiso 1 1 calc R U . . . H21C H 0.739493 0.669971 0.449234 0.049 Uiso 1 1 calc R U . . . C22 C 0.2503(8) 0.7344(8) 0.8028(5) 0.0341(14) Uani 1 1 d . . . . . H22A H 0.185537 0.839253 0.766175 0.051 Uiso 1 1 calc R U . . . H22B H 0.318248 0.746591 0.859203 0.051 Uiso 1 1 calc R U . . . H22C H 0.178566 0.647606 0.847389 0.051 Uiso 1 1 calc R U . . . C23 C 0.4309(7) 0.1461(7) 0.6959(5) 0.0306(12) Uani 1 1 d . . . . . C24 C 0.9085(6) 0.2010(7) 0.8291(5) 0.0276(11) Uani 1 1 d . . . . . 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 Zn1 0.0192(3) 0.0270(3) 0.0184(3) -0.0099(2) 0.0008(2) -0.0013(2) S1 0.0267(7) 0.0245(7) 0.0248(6) -0.0088(5) -0.0013(5) 0.0013(5) S2 0.0200(6) 0.0285(7) 0.0226(6) -0.0123(5) -0.0016(5) -0.0017(5) F1 0.083(3) 0.036(2) 0.052(2) -0.0081(18) -0.040(2) -0.011(2) F2 0.040(2) 0.040(2) 0.043(2) -0.0083(16) -0.0129(16) 0.0121(16) F3 0.049(2) 0.057(2) 0.0273(17) -0.0133(17) 0.0043(16) 0.0021(18) F4 0.060(3) 0.046(2) 0.0238(17) -0.0208(16) 0.0011(16) -0.0103(18) F5 0.049(2) 0.0284(18) 0.047(2) -0.0126(16) -0.0070(17) -0.0050(16) F6 0.032(2) 0.059(2) 0.059(2) -0.027(2) -0.0066(18) -0.0188(17) O1 0.034(2) 0.0242(19) 0.0275(19) -0.0064(15) -0.0049(16) 0.0008(16) O2 0.034(2) 0.064(3) 0.026(2) -0.006(2) 0.0016(18) 0.004(2) O3 0.051(3) 0.028(2) 0.045(2) -0.0162(19) -0.009(2) -0.0033(19) O4 0.038(2) 0.034(2) 0.033(2) -0.0117(18) -0.0053(17) 0.0042(18) O5 0.035(2) 0.046(2) 0.0216(18) -0.0146(17) -0.0012(16) -0.0040(18) O6 0.024(2) 0.041(2) 0.039(2) -0.0216(19) -0.0022(16) -0.0086(17) N1 0.017(2) 0.030(2) 0.024(2) -0.0126(19) 0.0020(17) 0.0017(18) N2 0.019(2) 0.025(2) 0.019(2) -0.0099(17) 0.0011(16) 0.0014(17) N3 0.024(2) 0.025(2) 0.020(2) -0.0127(17) 0.0051(17) -0.0025(18) N4 0.023(2) 0.023(2) 0.024(2) -0.0131(17) 0.0082(17) -0.0058(17) N5 0.029(2) 0.022(2) 0.019(2) -0.0088(17) -0.0029(17) 0.0043(17) N6 0.015(2) 0.025(2) 0.027(2) -0.0125(18) 0.0015(16) -0.0018(17) N7 0.014(2) 0.029(2) 0.0191(19) -0.0097(17) 0.0019(16) -0.0012(17) N8 0.015(2) 0.026(2) 0.019(2) -0.0111(18) 0.0034(17) -0.0028(17) C1 0.019(3) 0.034(3) 0.024(3) -0.012(2) 0.000(2) 0.000(2) C2 0.025(3) 0.032(3) 0.026(3) -0.012(2) -0.007(2) -0.003(2) C3 0.025(3) 0.027(3) 0.020(2) -0.011(2) -0.004(2) 0.000(2) C4 0.022(3) 0.051(4) 0.042(3) -0.021(3) 0.001(2) -0.008(3) C5 0.035(3) 0.037(3) 0.023(3) -0.016(2) 0.002(2) 0.002(3) C6 0.020(3) 0.022(2) 0.019(2) -0.008(2) -0.001(2) -0.001(2) C7 0.030(3) 0.025(3) 0.025(3) -0.009(2) -0.001(2) -0.002(2) C8 0.039(3) 0.027(3) 0.035(3) -0.012(2) 0.010(3) -0.006(2) C9 0.036(3) 0.024(3) 0.031(3) -0.011(2) 0.012(2) -0.012(2) C10 0.046(4) 0.026(3) 0.030(3) -0.015(2) 0.006(2) -0.009(2) C11 0.067(5) 0.041(4) 0.049(4) -0.026(3) 0.035(4) -0.023(3) C12 0.031(3) 0.026(3) 0.026(3) -0.006(2) -0.012(2) 0.002(2) C13 0.027(3) 0.028(3) 0.049(4) -0.010(3) -0.013(3) 0.009(2) C14 0.017(3) 0.030(3) 0.045(3) -0.019(2) -0.005(2) 0.003(2) C15 0.044(4) 0.042(3) 0.034(3) -0.005(3) -0.008(3) 0.008(3) C16 0.033(3) 0.046(4) 0.054(4) -0.026(3) -0.002(3) 0.010(3) C17 0.019(3) 0.030(3) 0.025(3) -0.012(2) 0.006(2) -0.002(2) C18 0.026(3) 0.022(3) 0.021(2) -0.005(2) -0.004(2) -0.005(2) C19 0.031(3) 0.025(3) 0.024(2) -0.008(2) -0.004(2) -0.009(2) C20 0.035(3) 0.018(2) 0.015(2) -0.0020(19) 0.001(2) -0.005(2) C21 0.019(3) 0.041(3) 0.042(3) -0.018(3) -0.005(2) 0.000(2) C22 0.042(4) 0.037(3) 0.030(3) -0.020(3) 0.004(3) -0.009(3) C23 0.034(3) 0.027(3) 0.028(3) -0.006(2) -0.005(2) -0.001(2) C24 0.026(3) 0.033(3) 0.029(3) -0.015(2) -0.002(2) -0.008(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 N5 Zn1 N7 90.82(16) . . ? N5 Zn1 N3 105.94(17) . . ? N7 Zn1 N3 95.93(16) . . ? N5 Zn1 N1 101.46(17) . . ? N7 Zn1 N1 165.39(16) . . ? N3 Zn1 N1 88.34(17) . . ? N5 Zn1 O1 105.18(16) . . ? N7 Zn1 O1 84.44(16) . . ? N3 Zn1 O1 148.86(15) . . ? N1 Zn1 O1 84.71(16) . . ? O3 S1 O2 118.1(3) . . ? O3 S1 O1 113.7(2) . . ? O2 S1 O1 111.8(3) . . ? O3 S1 C23 104.6(3) . . ? O2 S1 C23 103.6(3) . . ? O1 S1 C23 102.9(2) . . ? O6 S2 O5 115.1(2) . . ? O6 S2 O4 114.6(3) . . ? O5 S2 O4 115.0(2) . . ? O6 S2 C24 103.7(2) . . ? O5 S2 C24 103.3(2) . . ? O4 S2 C24 102.9(2) . . ? S1 O1 Zn1 115.4(2) . . ? C1 N1 N2 106.4(4) . . ? C1 N1 Zn1 132.2(3) . . ? N2 N1 Zn1 121.2(3) . . ? C3 N2 N1 110.2(4) . . ? C3 N2 C6 130.1(4) . . ? N1 N2 C6 119.0(4) . . ? C7 N3 N4 105.0(4) . . ? C7 N3 Zn1 132.6(3) . . ? N4 N3 Zn1 121.4(3) . . ? C9 N4 N3 111.5(4) . . ? C9 N4 C6 129.6(4) . . ? N3 N4 C6 118.8(4) . . ? C12 N5 N6 106.4(4) . . ? C12 N5 Zn1 133.2(4) . . ? N6 N5 Zn1 118.3(3) . . ? C14 N6 N5 111.1(4) . . ? C14 N6 C17 130.3(4) . . ? N5 N6 C17 118.6(4) . . ? C18 N7 N8 105.2(4) . . ? C18 N7 Zn1 136.7(3) . . ? N8 N7 Zn1 118.0(3) . . ? C20 N8 N7 111.2(4) . . ? C20 N8 C17 130.2(4) . . ? N7 N8 C17 118.3(4) . . ? N1 C1 C2 109.9(5) . . ? N1 C1 C4 121.7(5) . . ? C2 C1 C4 128.5(5) . . ? C3 C2 C1 106.3(5) . . ? C3 C2 H2 126.9 . . ? C1 C2 H2 126.9 . . ? N2 C3 C2 107.2(4) . . ? N2 C3 C5 122.9(5) . . ? C2 C3 C5 129.9(5) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 N4 112.1(4) . . ? N2 C6 H6A 109.2 . . ? N4 C6 H6A 109.2 . . ? N2 C6 H6B 109.2 . . ? N4 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N3 C7 C8 110.5(5) . . ? N3 C7 C10 122.3(5) . . ? C8 C7 C10 127.2(5) . . ? C9 C8 C7 106.3(5) . . ? C9 C8 H8 126.8 . . ? C7 C8 H8 126.8 . . ? N4 C9 C8 106.7(5) . . ? N4 C9 C11 122.9(5) . . ? C8 C9 C11 130.4(5) . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N5 C12 C13 108.7(5) . . ? N5 C12 C15 122.1(5) . . ? C13 C12 C15 129.2(5) . . ? C14 C13 C12 107.3(5) . . ? C14 C13 H13 126.4 . . ? C12 C13 H13 126.4 . . ? N6 C14 C13 106.5(5) . . ? N6 C14 C16 122.7(5) . . ? C13 C14 C16 130.8(5) . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N6 C17 N8 112.1(4) . . ? N6 C17 H17A 109.2 . . ? N8 C17 H17A 109.2 . . ? N6 C17 H17B 109.2 . . ? N8 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? N7 C18 C19 110.0(5) . . ? N7 C18 C21 121.0(4) . . ? C19 C18 C21 129.0(5) . . ? C20 C19 C18 106.7(5) . . ? C20 C19 H19 126.6 . . ? C18 C19 H19 126.6 . . ? N8 C20 C19 106.8(4) . . ? N8 C20 C22 121.9(5) . . ? C19 C20 C22 131.2(5) . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? F1 C23 F3 107.4(5) . . ? F1 C23 F2 108.6(5) . . ? F3 C23 F2 107.8(5) . . ? F1 C23 S1 111.7(4) . . ? F3 C23 S1 111.0(4) . . ? F2 C23 S1 110.1(4) . . ? F6 C24 F5 107.4(4) . . ? F6 C24 F4 107.8(4) . . ? F5 C24 F4 107.5(4) . . ? F6 C24 S2 111.5(4) . . ? F5 C24 S2 111.6(4) . . ? F4 C24 S2 110.7(4) . . ? 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 Zn1 N5 2.057(4) . ? Zn1 N7 2.080(4) . ? Zn1 N3 2.082(4) . ? Zn1 N1 2.096(5) . ? Zn1 O1 2.178(4) . ? S1 O3 1.421(4) . ? S1 O2 1.439(5) . ? S1 O1 1.456(4) . ? S1 C23 1.838(6) . ? S2 O6 1.435(4) . ? S2 O5 1.444(4) . ? S2 O4 1.447(4) . ? S2 C24 1.820(5) . ? F1 C23 1.308(7) . ? F2 C23 1.332(6) . ? F3 C23 1.321(7) . ? F4 C24 1.344(6) . ? F5 C24 1.332(7) . ? F6 C24 1.315(6) . ? N1 C1 1.337(7) . ? N1 N2 1.376(6) . ? N2 C3 1.366(7) . ? N2 C6 1.436(7) . ? N3 C7 1.330(7) . ? N3 N4 1.381(5) . ? N4 C9 1.334(7) . ? N4 C6 1.442(6) . ? N5 C12 1.342(7) . ? N5 N6 1.363(5) . ? N6 C14 1.356(7) . ? N6 C17 1.438(7) . ? N7 C18 1.337(7) . ? N7 N8 1.378(6) . ? N8 C20 1.345(7) . ? N8 C17 1.444(7) . ? C1 C2 1.408(7) . ? C1 C4 1.492(8) . ? C2 C3 1.373(8) . ? C2 H2 0.9500 . ? C3 C5 1.497(7) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.390(8) . ? C7 C10 1.522(7) . ? C8 C9 1.376(8) . ? C8 H8 0.9500 . ? C9 C11 1.503(8) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.406(8) . ? C12 C15 1.487(8) . ? C13 C14 1.362(9) . ? C13 H13 0.9500 . ? C14 C16 1.493(8) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.397(7) . ? C18 C21 1.489(7) . ? C19 C20 1.364(8) . ? C19 H19 0.9500 . ? C20 C22 1.491(7) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 O3 S1 O1 Zn1 -132.9(3) . . . . ? O2 S1 O1 Zn1 4.0(3) . . . . ? C23 S1 O1 Zn1 114.6(3) . . . . ? C1 N1 N2 C3 -0.9(6) . . . . ? Zn1 N1 N2 C3 -176.7(3) . . . . ? C1 N1 N2 C6 -172.1(4) . . . . ? Zn1 N1 N2 C6 12.0(6) . . . . ? C7 N3 N4 C9 0.8(6) . . . . ? Zn1 N3 N4 C9 170.5(4) . . . . ? C7 N3 N4 C6 177.5(4) . . . . ? Zn1 N3 N4 C6 -12.8(6) . . . . ? C12 N5 N6 C14 -0.1(6) . . . . ? Zn1 N5 N6 C14 165.2(3) . . . . ? C12 N5 N6 C17 -179.9(5) . . . . ? Zn1 N5 N6 C17 -14.5(6) . . . . ? C18 N7 N8 C20 -0.6(6) . . . . ? Zn1 N7 N8 C20 -177.5(3) . . . . ? C18 N7 N8 C17 -175.4(5) . . . . ? Zn1 N7 N8 C17 7.7(6) . . . . ? N2 N1 C1 C2 0.4(6) . . . . ? Zn1 N1 C1 C2 175.6(4) . . . . ? N2 N1 C1 C4 -178.8(5) . . . . ? Zn1 N1 C1 C4 -3.6(8) . . . . ? N1 C1 C2 C3 0.2(6) . . . . ? C4 C1 C2 C3 179.3(6) . . . . ? N1 N2 C3 C2 1.0(6) . . . . ? C6 N2 C3 C2 171.0(5) . . . . ? N1 N2 C3 C5 -177.6(5) . . . . ? C6 N2 C3 C5 -7.5(8) . . . . ? C1 C2 C3 N2 -0.7(6) . . . . ? C1 C2 C3 C5 177.7(5) . . . . ? C3 N2 C6 N4 126.5(5) . . . . ? N1 N2 C6 N4 -64.2(6) . . . . ? C9 N4 C6 N2 -119.3(6) . . . . ? N3 N4 C6 N2 64.8(6) . . . . ? N4 N3 C7 C8 -0.8(6) . . . . ? Zn1 N3 C7 C8 -168.8(4) . . . . ? N4 N3 C7 C10 178.0(5) . . . . ? Zn1 N3 C7 C10 10.0(8) . . . . ? N3 C7 C8 C9 0.5(7) . . . . ? C10 C7 C8 C9 -178.3(6) . . . . ? N3 N4 C9 C8 -0.5(7) . . . . ? C6 N4 C9 C8 -176.7(5) . . . . ? N3 N4 C9 C11 178.9(6) . . . . ? C6 N4 C9 C11 2.7(10) . . . . ? C7 C8 C9 N4 0.0(7) . . . . ? C7 C8 C9 C11 -179.4(7) . . . . ? N6 N5 C12 C13 -0.3(6) . . . . ? Zn1 N5 C12 C13 -162.5(4) . . . . ? N6 N5 C12 C15 177.9(5) . . . . ? Zn1 N5 C12 C15 15.7(9) . . . . ? N5 C12 C13 C14 0.6(7) . . . . ? C15 C12 C13 C14 -177.4(6) . . . . ? N5 N6 C14 C13 0.5(6) . . . . ? C17 N6 C14 C13 -179.8(5) . . . . ? N5 N6 C14 C16 -179.0(5) . . . . ? C17 N6 C14 C16 0.7(9) . . . . ? C12 C13 C14 N6 -0.7(7) . . . . ? C12 C13 C14 C16 178.8(6) . . . . ? C14 N6 C17 N8 -110.3(6) . . . . ? N5 N6 C17 N8 69.3(6) . . . . ? C20 N8 C17 N6 121.9(6) . . . . ? N7 N8 C17 N6 -64.6(6) . . . . ? N8 N7 C18 C19 0.1(6) . . . . ? Zn1 N7 C18 C19 176.1(4) . . . . ? N8 N7 C18 C21 179.0(5) . . . . ? Zn1 N7 C18 C21 -5.0(8) . . . . ? N7 C18 C19 C20 0.4(6) . . . . ? C21 C18 C19 C20 -178.4(5) . . . . ? N7 N8 C20 C19 0.9(6) . . . . ? C17 N8 C20 C19 174.8(5) . . . . ? N7 N8 C20 C22 -178.5(5) . . . . ? C17 N8 C20 C22 -4.6(9) . . . . ? C18 C19 C20 N8 -0.7(6) . . . . ? C18 C19 C20 C22 178.6(5) . . . . ? O3 S1 C23 F1 -175.4(4) . . . . ? O2 S1 C23 F1 60.3(5) . . . . ? O1 S1 C23 F1 -56.3(5) . . . . ? O3 S1 C23 F3 -55.5(4) . . . . ? O2 S1 C23 F3 -179.9(4) . . . . ? O1 S1 C23 F3 63.5(4) . . . . ? O3 S1 C23 F2 63.8(5) . . . . ? O2 S1 C23 F2 -60.5(5) . . . . ? O1 S1 C23 F2 -177.1(4) . . . . ? O6 S2 C24 F6 178.4(4) . . . . ? O5 S2 C24 F6 58.0(4) . . . . ? O4 S2 C24 F6 -62.0(4) . . . . ? O6 S2 C24 F5 58.2(4) . . . . ? O5 S2 C24 F5 -62.2(4) . . . . ? O4 S2 C24 F5 177.9(4) . . . . ? O6 S2 C24 F4 -61.6(4) . . . . ? O5 S2 C24 F4 178.0(4) . . . . ? O4 S2 C24 F4 58.1(4) . . . . ?