#------------------------------------------------------------------------------ #$Date: 2025-08-21 23:24:23 +0100 (Thu, 21 Aug 2025) $ #$Revision: 301857 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/26/7112616.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_7112616 loop_ _publ_author_name 'Alicea A. Leitch' 'Ilia Korobkov' 'Abdeljalil Assoud' 'Jaclyn L. Brusso' _publ_section_title ; Non-innocent pyridyl nitrogens: unprecedented interconversion of N-bridgehead-thiadiazolium salts and thiatriazine in the generation of thiatriazinyl ; _journal_name_full Chem.Commun. _journal_page_first 4934 _journal_paper_doi 10.1039/C4CC01433B _journal_volume 50 _journal_year 2014 _chemical_formula_sum 'C14 H11 F6 N5 O6 S3' _chemical_formula_weight 555.46 _chemical_melting_point 275 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _cell_angle_alpha 94.5844(16) _cell_angle_beta 102.6573(17) _cell_angle_gamma 92.0173(17) _cell_formula_units_Z 2 _cell_length_a 9.1987(3) _cell_length_b 9.8364(3) _cell_length_c 11.7652(4) _cell_measurement_reflns_used 6909 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 28.35 _cell_measurement_theta_min 2.27 _cell_volume 1033.82(6) _computing_cell_refinement 'APEX II, Bruker (2009)' _computing_data_collection 'APEX II, Bruker (2009)' _computing_data_reduction 'XPREP, Bruker (2009)' _computing_molecular_graphics 'SHELXTL, Bruker (2004)' _computing_publication_material 'SHELXTL, Bruker (2004)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-03 (Sheldrick, 2003)' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0350 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 14565 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.363 _diffrn_reflns_theta_min 1.781 _exptl_absorpt_coefficient_mu 0.458 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6426 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_meas ? _exptl_crystal_description needle _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.893 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 5084 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0471 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+0.3850P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1138 _refine_ls_wR_factor_ref 0.1220 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3959 _reflns_number_total 5084 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c4cc01433b2.cif _cod_data_source_block jb014 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 7112616 #BEGIN Tags that were not found in dictionaries: _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 0.922 _shelx_estimated_absorpt_t_max 0.973 _shelxl_version_number 2013-4 _shelx_res_file ; TITL jb014 in P-1 CELL 0.71073 9.19870 9.83640 11.76520 94.5844 102.6573 92.0173 ZERR 2.00 0.00030 0.00030 0.00040 0.0016 0.0017 0.0017 LATT 1 SFAC C H N O F S UNIT 28 22 10 12 12 6 TEMP -73.15C SIZE 0.06 0.08 0.18 L.S. 80 ACTA CONF BOND FMAP 2 PLAN 5 LIST 0 OMIT 1 0 0 OMIT 0 5 2 OMIT -3 1 2 OMIT -2 1 2 OMIT 1 -1 1 OMIT 1 -4 2 OMIT 0 0 6 OMIT 0 -2 5 OMIT 3 -1 2 OMIT 0 2 3 OMIT -11 -1 8 OMIT -10 -2 7 OMIT -3 -5 3 OMIT -2 0 1 OMIT 2 1 1 OMIT -1 -1 5 OMIT -10 -2 8 OMIT -3 -5 8 OMIT -2 2 7 OMIT -1 6 6 OMIT -3 -4 2 OMIT 4 -4 1 OMIT -12 -1 3 OMIT -11 -2 7 OMIT -10 -1 7 OMIT 1 1 1 OMIT -1 3 14 OMIT -4 5 0 OMIT 4 1 0 OMIT 0 -5 2 OMIT -4 -2 8 OMIT -11 2 1 OMIT 4 0 0 OMIT -1 -2 1 OMIT 0 -1 14 OMIT -2 -3 6 OMIT 0 4 2 OMIT -4 -2 2 OMIT 5 -1 2 OMIT 9 -6 5 OMIT -1 7 3 OMIT 1 1 4 OMIT -5 2 7 OMIT 3 -1 4 OMIT 5 2 3 OMIT -4 1 4 OMIT 1 2 5 OMIT -4 1 1 OMIT 3 1 4 OMIT 0 -2 3 WGHT 0.068900 0.385000 FVAR 0.20368 S1 6 0.728687 1.005516 -0.353894 11.00000 0.05057 0.02368 = 0.02122 0.00495 0.00468 -0.00084 S2 6 0.154839 0.825817 0.648361 11.00000 0.03155 0.03452 = 0.01897 0.00327 0.00545 0.00312 S3 6 0.297343 0.685560 0.140295 11.00000 0.03118 0.01840 = 0.02751 0.00195 0.00999 0.00026 F1 5 0.425340 0.861895 0.776469 11.00000 0.04638 0.07334 = 0.10150 -0.02757 -0.01628 -0.01309 F2 5 0.344613 0.653434 0.743017 11.00000 0.08161 0.05111 = 0.10129 0.01795 -0.02116 0.02101 F3 5 0.408086 0.757389 0.605908 11.00000 0.04905 0.10313 = 0.12287 -0.03177 0.04926 -0.00270 F4 5 0.502255 0.860436 0.113506 11.00000 0.08229 0.08381 = 0.16097 0.01558 0.04354 -0.04794 F5 5 0.585132 0.673214 0.177874 11.00000 0.03580 0.20715 = 0.06639 0.05331 0.00991 0.03648 F6 5 0.480312 0.679177 0.000575 11.00000 0.07698 0.14668 = 0.04725 0.02457 0.03785 0.03436 O1 4 0.175782 0.946898 0.593732 11.00000 0.09422 0.04461 = 0.05148 0.02371 0.02301 0.01215 O2 4 0.082621 0.709710 0.573006 11.00000 0.04655 0.05836 = 0.02456 -0.00503 -0.00251 -0.00946 O3 4 0.103515 0.848689 0.755073 11.00000 0.04947 0.05946 = 0.03407 -0.01126 0.02204 -0.00472 O4 4 0.316241 0.738902 0.260046 11.00000 0.06365 0.03787 = 0.03135 0.00225 0.01611 0.01237 O5 4 0.286442 0.538748 0.123421 11.00000 0.08811 0.02059 = 0.04355 0.00397 0.00839 -0.00504 O6 4 0.192625 0.750475 0.055811 11.00000 0.03281 0.03612 = 0.04321 0.00157 0.00111 0.00717 N2 3 0.815004 0.776434 -0.105447 11.00000 0.02698 0.02412 = 0.01834 0.00380 0.00338 0.00010 N1 3 0.768025 0.970598 -0.217203 11.00000 0.03627 0.02451 = 0.02187 0.00256 0.00619 -0.00041 N4 3 0.723911 0.836155 -0.406503 11.00000 0.03113 0.02473 = 0.01875 0.00278 0.00584 -0.00141 N3 3 0.828871 0.978700 0.021549 11.00000 0.04277 0.02906 = 0.01930 0.00071 0.00702 0.00382 AFIX 93 H3B 2 0.807090 1.032160 -0.035647 11.00000 -1.20000 H3C 2 0.845636 1.013655 0.094748 11.00000 -1.20000 AFIX 0 N5 3 0.858781 0.625201 0.070040 11.00000 0.02989 0.03256 = 0.01973 0.00481 0.00677 0.00421 AFIX 43 H5B 2 0.826989 0.594982 -0.004047 11.00000 -1.20000 AFIX 0 C1 1 0.780558 0.839057 -0.205929 11.00000 0.02213 0.02163 = 0.02233 0.00233 0.00614 0.00010 C2 1 0.836401 0.845957 -0.002476 11.00000 0.02156 0.03018 = 0.02101 0.00308 0.00579 -0.00096 C3 1 0.751875 0.755959 -0.316682 11.00000 0.02232 0.02476 = 0.01800 0.00222 0.00534 0.00102 C4 1 0.745044 0.615019 -0.339491 11.00000 0.03416 0.02631 = 0.02546 0.00493 0.00494 0.00293 AFIX 43 H4A 2 0.765222 0.557692 -0.277248 11.00000 -1.20000 AFIX 0 C5 1 0.708732 0.560195 -0.453214 11.00000 0.04552 0.02726 = 0.03377 -0.00259 0.00831 0.00087 AFIX 43 H5A 2 0.703256 0.463924 -0.470680 11.00000 -1.20000 AFIX 0 C6 1 0.679618 0.646182 -0.543923 11.00000 0.04604 0.03960 = 0.02190 -0.00672 0.00875 -0.00326 AFIX 43 H6A 2 0.654240 0.607776 -0.622865 11.00000 -1.20000 AFIX 0 C7 1 0.687305 0.783534 -0.520155 11.00000 0.04315 0.03702 = 0.01793 0.00348 0.00635 -0.00380 AFIX 43 H7A 2 0.667530 0.841961 -0.581622 11.00000 -1.20000 AFIX 0 C8 1 0.874410 0.760313 0.097729 11.00000 0.02017 0.03400 = 0.02049 0.00620 0.00617 0.00107 C9 1 0.923635 0.808437 0.212790 11.00000 0.02786 0.03920 = 0.02178 0.00354 0.00606 0.00043 AFIX 43 H9A 2 0.935203 0.903939 0.234711 11.00000 -1.20000 AFIX 0 C10 1 0.956548 0.716114 0.297296 11.00000 0.02984 0.05529 = 0.01716 0.00793 0.00225 0.00232 AFIX 43 H10A 2 0.991238 0.748652 0.377262 11.00000 -1.20000 AFIX 0 C11 1 0.939039 0.578179 0.265453 11.00000 0.03171 0.04793 = 0.02959 0.01873 0.00839 0.00789 AFIX 43 H11A 2 0.961120 0.514663 0.322763 11.00000 -1.20000 AFIX 0 C12 1 0.888929 0.533498 0.149028 11.00000 0.03353 0.03358 = 0.03531 0.01029 0.00937 0.00589 AFIX 43 H12A 2 0.875859 0.438513 0.124950 11.00000 -1.20000 AFIX 0 C13 1 0.342611 0.772380 0.697770 11.00000 0.03222 0.04296 = 0.05942 -0.01061 0.00599 -0.00305 C14 1 0.475809 0.727861 0.106348 11.00000 0.03644 0.07746 = 0.03739 0.01247 0.01029 0.00742 HKLF 4 REM jb014 in P-1 REM R1 = 0.0471 for 3959 Fo > 4sig(Fo) and 0.0652 for all 5084 data REM 307 parameters refined using 0 restraints END WGHT 0.0678 0.4071 REM Highest difference peak 0.893, deepest hole -0.355, 1-sigma level 0.067 Q1 1 0.9029 0.9390 0.1921 11.00000 0.05 0.89 Q2 1 0.1330 0.7533 0.6195 11.00000 0.05 0.58 Q3 1 0.3151 0.7063 0.2045 11.00000 0.05 0.51 Q4 1 0.5254 0.5946 0.1573 11.00000 0.05 0.47 Q5 1 0.2464 0.7964 0.6673 11.00000 0.05 0.46 ; _shelx_res_checksum 54289 #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_xyz 'x, y, z' '-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 S1 S 0.72869(7) 1.00552(6) -0.35389(5) 0.03224(15) Uani 1 1 d . . S2 S 0.15484(6) 0.82582(6) 0.64836(5) 0.02829(14) Uani 1 1 d . . S3 S 0.29734(6) 0.68556(5) 0.14030(5) 0.02520(14) Uani 1 1 d . . F1 F 0.4253(2) 0.8619(2) 0.7765(2) 0.0811(7) Uani 1 1 d . . F2 F 0.3446(3) 0.6534(2) 0.7430(2) 0.0834(7) Uani 1 1 d . . F3 F 0.4081(2) 0.7574(3) 0.6059(2) 0.0895(8) Uani 1 1 d . . F4 F 0.5023(3) 0.8604(3) 0.1135(3) 0.1075(9) Uani 1 1 d . . F5 F 0.5851(2) 0.6732(3) 0.17787(19) 0.1004(10) Uani 1 1 d . . F6 F 0.4803(3) 0.6792(3) 0.00057(18) 0.0850(7) Uani 1 1 d . . O1 O 0.1758(3) 0.9469(2) 0.59373(19) 0.0611(6) Uani 1 1 d . . O2 O 0.0826(2) 0.7097(2) 0.57301(15) 0.0455(5) Uani 1 1 d . . O3 O 0.1035(2) 0.8487(2) 0.75507(16) 0.0467(5) Uani 1 1 d . . O4 O 0.3162(2) 0.73890(19) 0.26005(16) 0.0433(4) Uani 1 1 d . . O5 O 0.2864(3) 0.53875(17) 0.12342(17) 0.0518(5) Uani 1 1 d . . O6 O 0.19263(19) 0.75048(18) 0.05581(16) 0.0385(4) Uani 1 1 d . . N2 N 0.8150(2) 0.77643(18) -0.10545(15) 0.0233(4) Uani 1 1 d . . N1 N 0.7680(2) 0.97060(19) -0.21720(16) 0.0276(4) Uani 1 1 d . . N4 N 0.7239(2) 0.83616(18) -0.40650(15) 0.0249(4) Uani 1 1 d . . N3 N 0.8289(2) 0.97870(19) 0.02155(16) 0.0304(4) Uani 1 1 d . . H3B H 0.8071 1.0322 -0.0356 0.036 Uiso 1 1 calc R U H3C H 0.8456 1.0137 0.0947 0.036 Uiso 1 1 calc R U N5 N 0.8588(2) 0.62520(19) 0.07004(16) 0.0270(4) Uani 1 1 d . . H5B H 0.8270 0.5950 -0.0040 0.032 Uiso 1 1 calc R U C1 C 0.7806(2) 0.8391(2) -0.20593(18) 0.0219(4) Uani 1 1 d . . C2 C 0.8364(2) 0.8460(2) -0.00248(18) 0.0241(4) Uani 1 1 d . . C3 C 0.7519(2) 0.7560(2) -0.31668(17) 0.0216(4) Uani 1 1 d . . C4 C 0.7450(3) 0.6150(2) -0.3395(2) 0.0287(5) Uani 1 1 d . . H4A H 0.7652 0.5577 -0.2772 0.034 Uiso 1 1 calc R U C5 C 0.7087(3) 0.5602(2) -0.4532(2) 0.0359(5) Uani 1 1 d . . H5A H 0.7033 0.4639 -0.4707 0.043 Uiso 1 1 calc R U C6 C 0.6796(3) 0.6462(3) -0.5439(2) 0.0363(5) Uani 1 1 d . . H6A H 0.6542 0.6078 -0.6229 0.044 Uiso 1 1 calc R U C7 C 0.6873(3) 0.7835(3) -0.52016(19) 0.0329(5) Uani 1 1 d . . H7A H 0.6675 0.8420 -0.5816 0.039 Uiso 1 1 calc R U C8 C 0.8744(2) 0.7603(2) 0.09773(18) 0.0244(4) Uani 1 1 d . . C9 C 0.9236(2) 0.8084(3) 0.21279(19) 0.0295(5) Uani 1 1 d . . H9A H 0.9352 0.9039 0.2347 0.035 Uiso 1 1 calc R U C10 C 0.9565(3) 0.7161(3) 0.2973(2) 0.0343(5) Uani 1 1 d . . H10A H 0.9912 0.7487 0.3773 0.041 Uiso 1 1 calc R U C11 C 0.9390(3) 0.5782(3) 0.2655(2) 0.0352(5) Uani 1 1 d . . H11A H 0.9611 0.5147 0.3228 0.042 Uiso 1 1 calc R U C12 C 0.8889(3) 0.5335(3) 0.1490(2) 0.0334(5) Uani 1 1 d . . H12A H 0.8759 0.4385 0.1249 0.040 Uiso 1 1 calc R U C13 C 0.3426(3) 0.7724(3) 0.6978(3) 0.0465(7) Uani 1 1 d . . C14 C 0.4758(3) 0.7279(4) 0.1063(3) 0.0496(7) 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 S1 0.0506(4) 0.0237(3) 0.0212(3) 0.0050(2) 0.0047(2) -0.0008(2) S2 0.0315(3) 0.0345(3) 0.0190(3) 0.0033(2) 0.0054(2) 0.0031(2) S3 0.0312(3) 0.0184(2) 0.0275(3) 0.00195(19) 0.0100(2) 0.00026(19) F1 0.0464(11) 0.0733(14) 0.1015(17) -0.0276(12) -0.0163(11) -0.0131(9) F2 0.0816(15) 0.0511(11) 0.1013(17) 0.0179(11) -0.0212(12) 0.0210(10) F3 0.0490(12) 0.1031(18) 0.123(2) -0.0318(15) 0.0493(13) -0.0027(11) F4 0.0823(17) 0.0838(17) 0.161(3) 0.0156(17) 0.0435(17) -0.0479(13) F5 0.0358(10) 0.207(3) 0.0664(14) 0.0533(17) 0.0099(9) 0.0365(14) F6 0.0770(14) 0.147(2) 0.0473(11) 0.0246(13) 0.0378(10) 0.0344(14) O1 0.0942(18) 0.0446(12) 0.0515(13) 0.0237(10) 0.0230(12) 0.0121(11) O2 0.0465(11) 0.0584(12) 0.0246(9) -0.0050(8) -0.0025(8) -0.0095(9) O3 0.0495(11) 0.0595(12) 0.0341(10) -0.0113(9) 0.0220(9) -0.0047(9) O4 0.0637(12) 0.0379(10) 0.0313(9) 0.0023(7) 0.0161(9) 0.0124(9) O5 0.0881(16) 0.0206(9) 0.0435(11) 0.0040(8) 0.0084(10) -0.0050(9) O6 0.0328(9) 0.0361(9) 0.0432(10) 0.0016(8) 0.0011(8) 0.0072(7) N2 0.0270(9) 0.0241(9) 0.0183(8) 0.0038(7) 0.0034(7) 0.0001(7) N1 0.0363(10) 0.0245(9) 0.0219(9) 0.0026(7) 0.0062(8) -0.0004(7) N4 0.0311(10) 0.0247(9) 0.0187(8) 0.0028(7) 0.0058(7) -0.0014(7) N3 0.0428(11) 0.0291(10) 0.0193(9) 0.0007(7) 0.0070(8) 0.0038(8) N5 0.0299(10) 0.0326(10) 0.0197(9) 0.0048(7) 0.0068(7) 0.0042(7) C1 0.0221(10) 0.0216(9) 0.0223(10) 0.0023(8) 0.0061(8) 0.0001(7) C2 0.0216(10) 0.0302(11) 0.0210(10) 0.0031(8) 0.0058(8) -0.0010(8) C3 0.0223(10) 0.0248(10) 0.0180(10) 0.0022(8) 0.0053(8) 0.0010(8) C4 0.0342(12) 0.0263(11) 0.0255(11) 0.0049(9) 0.0049(9) 0.0029(9) C5 0.0455(14) 0.0273(12) 0.0338(13) -0.0026(10) 0.0083(11) 0.0009(10) C6 0.0460(14) 0.0396(13) 0.0219(11) -0.0067(10) 0.0087(10) -0.0033(11) C7 0.0432(14) 0.0370(12) 0.0179(10) 0.0035(9) 0.0064(9) -0.0038(10) C8 0.0202(10) 0.0340(11) 0.0205(10) 0.0062(8) 0.0062(8) 0.0011(8) C9 0.0279(11) 0.0392(12) 0.0218(11) 0.0035(9) 0.0061(9) 0.0004(9) C10 0.0298(12) 0.0553(15) 0.0172(10) 0.0079(10) 0.0022(9) 0.0023(10) C11 0.0317(12) 0.0479(14) 0.0296(12) 0.0187(11) 0.0084(10) 0.0079(10) C12 0.0335(12) 0.0336(12) 0.0353(13) 0.0103(10) 0.0094(10) 0.0059(9) C13 0.0322(14) 0.0430(15) 0.0594(18) -0.0106(13) 0.0060(13) -0.0031(11) C14 0.0364(15) 0.077(2) 0.0374(15) 0.0125(14) 0.0103(12) 0.0074(14) 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 N1 S1 N4 93.18(9) O1 S2 O2 116.54(13) O1 S2 O3 114.16(13) O2 S2 O3 114.26(12) O1 S2 C13 103.45(15) O2 S2 C13 102.68(12) O3 S2 C13 103.31(13) O6 S3 O4 116.42(11) O6 S3 O5 114.17(12) O4 S3 O5 113.85(11) O6 S3 C14 103.69(12) O4 S3 C14 103.63(13) O5 S3 C14 102.79(15) C2 N2 C1 121.40(18) C1 N1 S1 112.82(15) C3 N4 C7 122.28(19) C3 N4 S1 110.26(14) C7 N4 S1 127.30(16) C8 N5 C12 123.5(2) N1 C1 N2 127.8(2) N1 C1 C3 113.46(18) N2 C1 C3 118.72(18) N2 C2 N3 128.4(2) N2 C2 C8 113.85(19) N3 C2 C8 117.75(19) N4 C3 C4 119.83(19) N4 C3 C1 110.23(18) C4 C3 C1 129.89(19) C5 C4 C3 118.8(2) C4 C5 C6 119.9(2) C7 C6 C5 120.6(2) C6 C7 N4 118.6(2) N5 C8 C9 118.7(2) N5 C8 C2 115.64(19) C9 C8 C2 125.6(2) C8 C9 C10 119.4(2) C11 C10 C9 120.2(2) C10 C11 C12 118.8(2) N5 C12 C11 119.4(2) F1 C13 F2 108.0(3) F1 C13 F3 107.8(2) F2 C13 F3 107.2(3) F1 C13 S2 112.3(2) F2 C13 S2 112.1(2) F3 C13 S2 109.2(2) F6 C14 F4 107.6(3) F6 C14 F5 106.3(3) F4 C14 F5 109.4(3) F6 C14 S3 111.5(2) F4 C14 S3 111.2(2) F5 C14 S3 110.7(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 N1 1.6362(19) S1 N4 1.7258(19) S2 O1 1.424(2) S2 O2 1.4347(19) S2 O3 1.4394(18) S2 C13 1.808(3) S3 O6 1.4313(18) S3 O4 1.4348(19) S3 O5 1.4388(17) S3 C14 1.815(3) F1 C13 1.314(3) F2 C13 1.323(4) F3 C13 1.349(4) F4 C14 1.311(4) F5 C14 1.322(3) F6 C14 1.307(4) N2 C2 1.314(3) N2 C1 1.358(3) N1 C1 1.318(3) N4 C3 1.354(3) N4 C7 1.360(3) N3 C2 1.321(3) N5 C8 1.338(3) N5 C12 1.339(3) C1 C3 1.449(3) C2 C8 1.490(3) C3 C4 1.387(3) C4 C5 1.367(3) C5 C6 1.400(4) C6 C7 1.354(3) C8 C9 1.369(3) C9 C10 1.392(3) C10 C11 1.373(4) C11 C12 1.376(4) 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 N4 S1 N1 C1 0.86(17) N1 S1 N4 C3 0.47(16) N1 S1 N4 C7 175.9(2) S1 N1 C1 N2 178.60(18) S1 N1 C1 C3 -1.9(2) C2 N2 C1 N1 2.1(3) C2 N2 C1 C3 -177.31(18) C1 N2 C2 N3 0.2(3) C1 N2 C2 C8 -179.52(18) C7 N4 C3 C4 0.7(3) S1 N4 C3 C4 176.34(16) C7 N4 C3 C1 -177.2(2) S1 N4 C3 C1 -1.5(2) N1 C1 C3 N4 2.2(3) N2 C1 C3 N4 -178.22(18) N1 C1 C3 C4 -175.4(2) N2 C1 C3 C4 4.2(3) N4 C3 C4 C5 -0.5(3) C1 C3 C4 C5 176.9(2) C3 C4 C5 C6 0.1(4) C4 C5 C6 C7 0.1(4) C5 C6 C7 N4 0.0(4) C3 N4 C7 C6 -0.4(3) S1 N4 C7 C6 -175.31(18) C12 N5 C8 C9 -0.1(3) C12 N5 C8 C2 179.5(2) N2 C2 C8 N5 -10.0(3) N3 C2 C8 N5 170.27(19) N2 C2 C8 C9 169.6(2) N3 C2 C8 C9 -10.1(3) N5 C8 C9 C10 0.3(3) C2 C8 C9 C10 -179.3(2) C8 C9 C10 C11 -0.3(3) C9 C10 C11 C12 0.1(4) C8 N5 C12 C11 -0.1(3) C10 C11 C12 N5 0.1(4) O1 S2 C13 F1 63.5(3) O2 S2 C13 F1 -174.9(2) O3 S2 C13 F1 -55.8(3) O1 S2 C13 F2 -174.8(2) O2 S2 C13 F2 -53.1(2) O3 S2 C13 F2 65.9(2) O1 S2 C13 F3 -56.1(2) O2 S2 C13 F3 65.5(2) O3 S2 C13 F3 -175.4(2) O6 S3 C14 F6 -61.4(2) O4 S3 C14 F6 176.5(2) O5 S3 C14 F6 57.7(2) O6 S3 C14 F4 58.7(2) O4 S3 C14 F4 -63.4(2) O5 S3 C14 F4 177.8(2) O6 S3 C14 F5 -179.6(2) O4 S3 C14 F5 58.4(3) O5 S3 C14 F5 -60.4(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139184539