#------------------------------------------------------------------------------ #$Date: 2021-05-28 06:47:23 +0300 (Fri, 28 May 2021) $ #$Revision: 265576 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158101.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_7158101 loop_ _publ_author_name 'Puji Pamungkas, Khurnia Krisna' 'Maruyama, Toshifumi' 'Murai, Toshiaki' _publ_section_title ; Boron complexes of thiazole-bridged 1,5-bidentate nitrogen ligands: synthesis and acid-responsive photophysical properties ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB00828E _journal_year 2021 _chemical_formula_moiety 'C20 H15 B F2 N4 S' _chemical_formula_sum 'C20 H15 B F2 N4 S' _chemical_formula_weight 392.23 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-04-28 deposited with the CCDC. 2021-05-26 downloaded from the CCDC. ; _cell_angle_alpha 105.166(3) _cell_angle_beta 96.037(2) _cell_angle_gamma 108.811(3) _cell_formula_units_Z 2 _cell_length_a 7.9896(2) _cell_length_b 9.2646(3) _cell_length_c 13.4601(4) _cell_measurement_reflns_used 2266 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31.0 _cell_measurement_theta_min 2.4 _cell_volume 890.46(5) _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)' _computing_data_collection 'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 14.6306 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Rigaku Mercury CCD (2x2 bin mode)' _diffrn_measurement_method 'profile data from \f-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_unetI/netI 0.0285 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8310 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.499 _diffrn_reflns_theta_min 2.446 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_type numerical _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.463 _exptl_crystal_description Block _exptl_crystal_F_000 404 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.206 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 4063 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0421 _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^)+(0.0537P)^2^+0.1258P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1007 _refine_ls_wR_factor_ref 0.1153 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2984 _reflns_number_total 4063 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00828e2.cif _cod_data_source_block 200715 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Numerical' was changed to 'numerical' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 7158101 _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. ; _shelx_estimated_absorpt_t_min 0.958 _shelx_estimated_absorpt_t_max 0.970 _shelx_res_file ; 200715.res created by SHELXL-2014/7 TITL REM Yadorkari-X generated CELL 0.71073 7.9896 9.2646 13.4601 105.1660 96.0370 108.8110 ZERR 2.0 0.0002 0.0003 0.0004 0.0030 0.0020 0.0030 LATT 1 REM SPGR P-1 triclinic SFAC C H B F N S UNIT 40 30 2 4 8 2 SIZE 0.20 0.17 0.14 TEMP 20.0 L.S. 30 FMAP 2 PLAN -20 ACTA CONF LIST 4 MERG 2 OMIT -10.000000 55.000000 FREE C15 B1 FREE N4 B1 WGHT 0.053700 0.125800 FVAR 2.93368 S1 6 0.960062 0.714083 0.454122 11.00000 0.04738 0.03891 = 0.04748 0.00842 0.00446 0.00008 F1 4 1.359696 0.789665 0.234640 11.00000 0.06020 0.05547 = 0.08329 0.00076 0.01999 0.01935 F2 4 1.196054 0.895109 0.147936 11.00000 0.07447 0.06653 = 0.04661 0.01409 0.00817 0.00288 N1 5 1.225142 0.974422 0.566975 11.00000 0.04290 0.03705 = 0.04491 0.00690 0.00671 0.00695 N2 5 1.079428 0.794867 0.284262 11.00000 0.04599 0.03717 = 0.04350 0.00471 0.00479 0.00442 N3 5 0.899949 0.695873 0.658077 11.00000 0.05272 0.05831 = 0.05775 0.02049 0.00884 0.00163 N4 5 1.357732 1.048103 0.326913 11.00000 0.04388 0.03912 = 0.04884 0.01120 0.00927 0.00855 C1 1 1.093121 0.854532 0.574223 11.00000 0.04158 0.03686 = 0.04591 0.00854 0.00530 0.00760 C2 1 1.095005 0.829177 0.389797 11.00000 0.04184 0.03431 = 0.04555 0.00882 0.00722 0.00863 C3 1 1.229787 0.962167 0.463020 11.00000 0.04158 0.03400 = 0.04483 0.00784 0.00720 0.00755 C4 1 0.923663 0.666071 0.215376 11.00000 0.04946 0.03733 = 0.04277 0.00610 0.00228 0.00542 C5 1 0.750825 0.656957 0.227430 11.00000 0.05223 0.04558 = 0.04678 0.00920 0.00607 0.00923 AFIX 43 H5 2 0.734449 0.736989 0.279275 11.00000 -1.20000 AFIX 0 C6 1 0.602394 0.528371 0.162094 11.00000 0.05128 0.06092 = 0.05245 0.01746 0.00371 0.00308 AFIX 43 H6 2 0.486905 0.523044 0.170952 11.00000 -1.20000 AFIX 0 C7 1 0.622316 0.407223 0.083641 11.00000 0.06251 0.05004 = 0.04405 0.01163 -0.00336 -0.00369 C8 1 0.794652 0.422182 0.070365 11.00000 0.07681 0.04749 = 0.05500 -0.00363 0.00534 0.00997 AFIX 43 H8 2 0.810868 0.344972 0.016325 11.00000 -1.20000 AFIX 0 C9 1 0.945107 0.549353 0.135402 11.00000 0.05602 0.04982 = 0.06218 -0.00050 0.00745 0.01147 AFIX 43 H9 2 1.060318 0.555978 0.125139 11.00000 -1.20000 AFIX 0 C10 1 0.461378 0.262657 0.014718 11.00000 0.08063 0.06735 = 0.05882 0.01008 -0.00720 -0.01435 AFIX 137 H10 2 0.494249 0.214183 -0.048683 11.00000 -1.50000 H10A 2 0.363270 0.296132 -0.002682 11.00000 -1.50000 H10B 2 0.424654 0.186068 0.051854 11.00000 -1.50000 AFIX 0 C11 1 1.045108 0.827819 0.671061 11.00000 0.04580 0.04227 = 0.04998 0.01200 0.00890 0.01273 C12 1 1.142780 0.931267 0.769846 11.00000 0.06382 0.04655 = 0.04931 0.00922 0.01014 0.00730 AFIX 43 H12 2 1.244328 1.020684 0.776516 11.00000 -1.20000 AFIX 0 C13 1 1.087212 0.899549 0.857335 11.00000 0.08441 0.06161 = 0.05090 0.01177 0.01343 0.01530 AFIX 43 H13 2 1.149534 0.968058 0.924258 11.00000 -1.20000 AFIX 0 C14 1 0.938047 0.765063 0.844905 11.00000 0.07989 0.08229 = 0.05938 0.02915 0.02621 0.02509 AFIX 43 H14 2 0.897680 0.740473 0.902942 11.00000 -1.20000 AFIX 0 C15 1 0.850367 0.668095 0.744411 11.00000 0.06225 0.07761 = 0.06936 0.03264 0.01592 0.00145 AFIX 43 H15 2 0.749787 0.577124 0.736351 11.00000 -1.20000 AFIX 0 C16 1 1.357615 1.080999 0.431572 11.00000 0.04029 0.03567 = 0.04685 0.00828 0.00687 0.01045 C17 1 1.477566 1.228165 0.502416 11.00000 0.04631 0.03761 = 0.05361 0.00796 0.00834 0.00691 AFIX 43 H17 2 1.479508 1.250701 0.574130 11.00000 -1.20000 AFIX 0 C18 1 1.591604 1.338399 0.465861 11.00000 0.04772 0.03744 = 0.06584 0.01019 0.00717 0.00380 AFIX 43 H18 2 1.671681 1.435789 0.512557 11.00000 -1.20000 AFIX 0 C19 1 1.586976 1.303869 0.358494 11.00000 0.05165 0.04690 = 0.06994 0.02455 0.01353 0.00352 AFIX 43 H19 2 1.662142 1.378476 0.332436 11.00000 -1.20000 AFIX 0 C20 1 1.470603 1.158984 0.291901 11.00000 0.05286 0.05317 = 0.05476 0.02091 0.01301 0.01039 AFIX 43 H20 2 1.468656 1.135539 0.220156 11.00000 -1.20000 AFIX 0 B1 3 1.244890 0.874644 0.242907 11.00000 0.05234 0.04294 = 0.04544 0.00506 0.00923 0.00846 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM REM R1 = 0.0421 for 2984 Fo > 4sig(Fo) and 0.0644 for all 4063 data REM 254 parameters refined using 0 restraints END WGHT 0.0537 0.1258 REM Highest difference peak 0.206, deepest hole -0.178, 1-sigma level 0.039 Q1 1 0.5232 0.1638 0.0113 11.00000 0.05 0.21 Q2 1 1.1475 0.8348 0.2653 11.00000 0.05 0.19 Q3 1 1.1888 0.8883 0.4338 11.00000 0.05 0.17 Q4 1 1.0794 0.8882 0.7164 11.00000 0.05 0.16 Q5 1 1.0765 0.8174 0.3300 11.00000 0.05 0.15 Q6 1 0.3519 0.2019 0.0449 11.00000 0.05 0.15 Q7 1 1.3110 0.9801 0.2958 11.00000 0.05 0.15 Q8 1 0.8208 0.3803 0.0634 11.00000 0.05 0.14 Q9 1 0.4660 0.2830 -0.0650 11.00000 0.05 0.14 Q10 1 0.5258 0.0659 0.0218 11.00000 0.05 0.14 Q11 1 1.5036 1.0782 0.2032 11.00000 0.05 0.13 Q12 1 1.4487 1.1424 0.4781 11.00000 0.05 0.13 Q13 1 0.9852 0.7706 0.6655 11.00000 0.05 0.13 Q14 1 1.2238 0.9799 0.5143 11.00000 0.05 0.13 Q15 1 1.3179 0.9959 0.4508 11.00000 0.05 0.13 Q16 1 1.0155 0.7367 0.2601 11.00000 0.05 0.13 Q17 1 1.0991 0.4984 0.1579 11.00000 0.05 0.13 Q18 1 0.6216 0.4451 0.1420 11.00000 0.05 0.12 Q19 1 1.3545 1.0568 0.3789 11.00000 0.05 0.12 Q20 1 0.7274 0.7649 0.8622 11.00000 0.05 0.12 ; _shelx_res_checksum 6869 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.96006(6) 0.71408(5) 0.45412(3) 0.05012(16) Uani 1 1 d . . . . . F1 F 1.35970(15) 0.78966(14) 0.23464(10) 0.0707(4) Uani 1 1 d . . . . . F2 F 1.19605(16) 0.89511(15) 0.14794(8) 0.0695(4) Uani 1 1 d . . . . . N1 N 1.22514(18) 0.97442(17) 0.56698(11) 0.0450(3) Uani 1 1 d . . . . . N2 N 1.07943(19) 0.79487(17) 0.28426(11) 0.0470(4) Uani 1 1 d . . . . . N3 N 0.8999(2) 0.6959(2) 0.65808(13) 0.0608(4) Uani 1 1 d . . . . . N4 N 1.35773(19) 1.04810(17) 0.32691(11) 0.0462(4) Uani 1 1 d . . . . . C1 C 1.0931(2) 0.8545(2) 0.57422(13) 0.0444(4) Uani 1 1 d . . . . . C2 C 1.0950(2) 0.82918(19) 0.38980(13) 0.0428(4) Uani 1 1 d . . . . . C3 C 1.2298(2) 0.9622(2) 0.46302(13) 0.0428(4) Uani 1 1 d . . . . . C4 C 0.9237(2) 0.6661(2) 0.21538(13) 0.0478(4) Uani 1 1 d . . . . . C5 C 0.7508(2) 0.6570(2) 0.22743(14) 0.0518(5) Uani 1 1 d . . . . . H5 H 0.7344 0.7370 0.2793 0.062 Uiso 1 1 calc R U . . . C6 C 0.6024(3) 0.5284(2) 0.16209(15) 0.0600(5) Uani 1 1 d . . . . . H6 H 0.4869 0.5230 0.1710 0.072 Uiso 1 1 calc R U . . . C7 C 0.6223(3) 0.4072(2) 0.08364(15) 0.0603(5) Uani 1 1 d . . . . . C8 C 0.7947(3) 0.4222(2) 0.07037(16) 0.0678(6) Uani 1 1 d . . . . . H8 H 0.8109 0.3450 0.0163 0.081 Uiso 1 1 calc R U . . . C9 C 0.9451(3) 0.5494(2) 0.13540(16) 0.0621(5) Uani 1 1 d . . . . . H9 H 1.0603 0.5560 0.1251 0.075 Uiso 1 1 calc R U . . . C10 C 0.4614(3) 0.2627(3) 0.01472(18) 0.0833(8) Uani 1 1 d . . . . . H10 H 0.4942 0.2142 -0.0487 0.125 Uiso 1 1 calc R U . . . H10A H 0.3633 0.2961 -0.0027 0.125 Uiso 1 1 calc R U . . . H10B H 0.4247 0.1861 0.0519 0.125 Uiso 1 1 calc R U . . . C11 C 1.0451(2) 0.8278(2) 0.67106(14) 0.0475(4) Uani 1 1 d . . . . . C12 C 1.1428(3) 0.9313(2) 0.76985(15) 0.0579(5) Uani 1 1 d . . . . . H12 H 1.2443 1.0207 0.7765 0.069 Uiso 1 1 calc R U . . . C13 C 1.0872(3) 0.8995(3) 0.85734(17) 0.0698(6) Uani 1 1 d . . . . . H13 H 1.1495 0.9681 0.9243 0.084 Uiso 1 1 calc R U . . . C14 C 0.9380(3) 0.7651(3) 0.84490(18) 0.0726(6) Uani 1 1 d . . . . . H14 H 0.8977 0.7405 0.9029 0.087 Uiso 1 1 calc R U . . . C15 C 0.8504(3) 0.6681(3) 0.74441(18) 0.0738(6) Uani 1 1 d . . . . . H15 H 0.7498 0.5771 0.7364 0.089 Uiso 1 1 calc R U . . . C16 C 1.3576(2) 1.0810(2) 0.43157(13) 0.0429(4) Uani 1 1 d . . . . . C17 C 1.4776(2) 1.2282(2) 0.50242(15) 0.0495(4) Uani 1 1 d . . . . . H17 H 1.4795 1.2507 0.5741 0.059 Uiso 1 1 calc R U . . . C18 C 1.5916(2) 1.3384(2) 0.46586(16) 0.0550(5) Uani 1 1 d . . . . . H18 H 1.6717 1.4358 0.5126 0.066 Uiso 1 1 calc R U . . . C19 C 1.5870(3) 1.3039(2) 0.35849(16) 0.0585(5) Uani 1 1 d . . . . . H19 H 1.6621 1.3785 0.3324 0.070 Uiso 1 1 calc R U . . . C20 C 1.4706(2) 1.1590(2) 0.29190(16) 0.0549(5) Uani 1 1 d . . . . . H20 H 1.4687 1.1355 0.2202 0.066 Uiso 1 1 calc R U . . . B1 B 1.2449(3) 0.8746(3) 0.24291(16) 0.0511(5) 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 0.0474(3) 0.0389(3) 0.0475(3) 0.00842(19) 0.00446(19) 0.00008(18) F1 0.0602(7) 0.0555(7) 0.0833(8) 0.0008(6) 0.0200(6) 0.0193(6) F2 0.0745(7) 0.0665(8) 0.0466(6) 0.0141(5) 0.0082(5) 0.0029(6) N1 0.0429(7) 0.0370(8) 0.0449(8) 0.0069(6) 0.0067(6) 0.0070(6) N2 0.0460(8) 0.0372(8) 0.0435(8) 0.0047(6) 0.0048(6) 0.0044(6) N3 0.0527(9) 0.0583(10) 0.0577(10) 0.0205(8) 0.0088(8) 0.0016(8) N4 0.0439(8) 0.0391(8) 0.0488(8) 0.0112(6) 0.0093(6) 0.0085(6) C1 0.0416(9) 0.0369(9) 0.0459(9) 0.0085(7) 0.0053(7) 0.0076(7) C2 0.0418(9) 0.0343(9) 0.0455(9) 0.0088(7) 0.0072(7) 0.0086(7) C3 0.0416(8) 0.0340(9) 0.0448(9) 0.0078(7) 0.0072(7) 0.0076(7) C4 0.0495(10) 0.0373(9) 0.0428(9) 0.0061(7) 0.0023(7) 0.0054(7) C5 0.0522(10) 0.0456(10) 0.0468(10) 0.0092(8) 0.0061(8) 0.0092(8) C6 0.0513(11) 0.0609(13) 0.0525(11) 0.0175(9) 0.0037(9) 0.0031(9) C7 0.0625(12) 0.0500(12) 0.0441(10) 0.0116(9) -0.0034(9) -0.0037(9) C8 0.0768(15) 0.0475(12) 0.0550(12) -0.0036(9) 0.0053(10) 0.0100(10) C9 0.0560(11) 0.0498(12) 0.0622(12) -0.0005(9) 0.0075(9) 0.0115(9) C10 0.0806(15) 0.0674(15) 0.0588(13) 0.0101(11) -0.0072(11) -0.0144(12) C11 0.0458(9) 0.0423(10) 0.0500(10) 0.0120(8) 0.0089(8) 0.0127(8) C12 0.0638(12) 0.0465(11) 0.0493(10) 0.0092(8) 0.0101(9) 0.0073(9) C13 0.0844(15) 0.0616(14) 0.0509(11) 0.0118(10) 0.0134(11) 0.0153(12) C14 0.0799(15) 0.0823(17) 0.0594(13) 0.0292(12) 0.0262(11) 0.0251(13) C15 0.0622(13) 0.0776(16) 0.0694(14) 0.0326(12) 0.0159(11) 0.0015(11) C16 0.0403(8) 0.0357(9) 0.0468(9) 0.0083(7) 0.0069(7) 0.0105(7) C17 0.0463(9) 0.0376(9) 0.0536(10) 0.0080(8) 0.0083(8) 0.0069(7) C18 0.0477(10) 0.0374(10) 0.0658(12) 0.0102(8) 0.0072(9) 0.0038(8) C19 0.0516(11) 0.0469(11) 0.0699(13) 0.0246(9) 0.0135(9) 0.0035(9) C20 0.0529(10) 0.0532(11) 0.0548(11) 0.0209(9) 0.0130(9) 0.0104(9) B1 0.0523(11) 0.0429(12) 0.0454(11) 0.0051(9) 0.0092(9) 0.0085(9) 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' B B 0.0013 0.0007 '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' 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 C2 S1 C1 88.61(8) . . ? C1 N1 C3 110.78(14) . . ? C2 N2 C4 119.55(15) . . ? C2 N2 B1 118.04(14) . . ? C4 N2 B1 121.44(14) . . ? C15 N3 C11 117.15(17) . . ? C20 N4 C16 119.73(15) . . ? N1 C1 C11 126.37(15) . . ? N1 C1 S1 115.54(14) . . ? C11 C1 S1 118.09(12) . . ? N2 C2 C3 123.95(16) . . ? N2 C2 S1 126.24(12) . . ? C3 C2 S1 109.77(13) . . ? N1 C3 C2 115.28(15) . . ? N1 C3 C16 122.92(14) . . ? C2 C3 C16 121.72(16) . . ? C9 C4 C5 119.22(16) . . ? C9 C4 N2 119.85(17) . . ? C5 C4 N2 120.93(16) . . ? C4 C5 C6 119.88(19) . . ? C5 C6 C7 121.5(2) . . ? C8 C7 C6 117.62(17) . . ? C8 C7 C10 120.5(2) . . ? C6 C7 C10 121.9(2) . . ? C7 C8 C9 121.8(2) . . ? C4 C9 C8 120.0(2) . . ? N3 C11 C12 122.36(18) . . ? N3 C11 C1 115.24(16) . . ? C12 C11 C1 122.40(17) . . ? C13 C12 C11 118.96(19) . . ? C12 C13 C14 119.1(2) . . ? C15 C14 C13 118.2(2) . . ? N3 C15 C14 124.2(2) . . ? N4 C16 C17 119.59(16) . . ? N4 C16 C3 117.05(14) . . ? C17 C16 C3 123.35(17) . . ? C18 C17 C16 119.95(18) . . ? C17 C18 C19 119.57(17) . . ? C20 C19 C18 119.04(18) . . ? N4 C20 C19 122.11(19) . . ? F2 B1 F1 110.26(17) . . ? F2 B1 N2 111.68(16) . . ? F1 B1 N2 111.77(17) . . ? 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 1.7283(18) . ? S1 C1 1.7557(17) . ? F1 B1 1.384(3) . ? F2 B1 1.375(2) . ? N1 C1 1.296(2) . ? N1 C3 1.379(2) . ? N2 C2 1.355(2) . ? N2 C4 1.433(2) . ? N2 B1 1.531(3) . ? N3 C15 1.327(3) . ? N3 C11 1.342(2) . ? N4 C20 1.355(2) . ? N4 C16 1.361(2) . ? C1 C11 1.456(3) . ? C2 C3 1.391(2) . ? C3 C16 1.430(2) . ? C4 C9 1.381(3) . ? C4 C5 1.385(3) . ? C5 C6 1.386(2) . ? C6 C7 1.389(3) . ? C7 C8 1.374(3) . ? C7 C10 1.515(3) . ? C8 C9 1.387(3) . ? C11 C12 1.389(2) . ? C12 C13 1.370(3) . ? C13 C14 1.376(3) . ? C14 C15 1.373(3) . ? C16 C17 1.404(2) . ? C17 C18 1.368(3) . ? C18 C19 1.390(3) . ? C19 C20 1.364(3) . ? 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 C11 -179.31(17) . . . . ? C3 N1 C1 S1 -0.2(2) . . . . ? C2 S1 C1 N1 -0.32(15) . . . . ? C2 S1 C1 C11 178.91(15) . . . . ? C4 N2 C2 C3 -172.50(17) . . . . ? B1 N2 C2 C3 18.6(3) . . . . ? C4 N2 C2 S1 10.2(2) . . . . ? B1 N2 C2 S1 -158.69(14) . . . . ? C1 S1 C2 N2 178.31(16) . . . . ? C1 S1 C2 C3 0.69(14) . . . . ? C1 N1 C3 C2 0.7(2) . . . . ? C1 N1 C3 C16 177.69(16) . . . . ? N2 C2 C3 N1 -178.65(16) . . . . ? S1 C2 C3 N1 -1.0(2) . . . . ? N2 C2 C3 C16 4.4(3) . . . . ? S1 C2 C3 C16 -177.96(14) . . . . ? C2 N2 C4 C9 -128.9(2) . . . . ? B1 N2 C4 C9 39.6(3) . . . . ? C2 N2 C4 C5 51.4(2) . . . . ? B1 N2 C4 C5 -140.14(19) . . . . ? C9 C4 C5 C6 2.4(3) . . . . ? N2 C4 C5 C6 -177.83(17) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C8 -2.3(3) . . . . ? C5 C6 C7 C10 177.44(18) . . . . ? C6 C7 C8 C9 2.8(3) . . . . ? C10 C7 C8 C9 -177.0(2) . . . . ? C5 C4 C9 C8 -2.0(3) . . . . ? N2 C4 C9 C8 178.27(18) . . . . ? C7 C8 C9 C4 -0.7(3) . . . . ? C15 N3 C11 C12 0.9(3) . . . . ? C15 N3 C11 C1 -179.25(18) . . . . ? N1 C1 C11 N3 178.75(18) . . . . ? S1 C1 C11 N3 -0.4(2) . . . . ? N1 C1 C11 C12 -1.4(3) . . . . ? S1 C1 C11 C12 179.47(15) . . . . ? N3 C11 C12 C13 -1.3(3) . . . . ? C1 C11 C12 C13 178.84(19) . . . . ? C11 C12 C13 C14 0.9(3) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C11 N3 C15 C14 -0.1(4) . . . . ? C13 C14 C15 N3 -0.2(4) . . . . ? C20 N4 C16 C17 -1.5(3) . . . . ? C20 N4 C16 C3 177.24(16) . . . . ? N1 C3 C16 N4 174.60(15) . . . . ? C2 C3 C16 N4 -8.6(3) . . . . ? N1 C3 C16 C17 -6.7(3) . . . . ? C2 C3 C16 C17 170.02(17) . . . . ? N4 C16 C17 C18 1.0(3) . . . . ? C3 C16 C17 C18 -177.62(17) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C17 C18 C19 C20 -1.2(3) . . . . ? C16 N4 C20 C19 0.6(3) . . . . ? C18 C19 C20 N4 0.7(3) . . . . ? C2 N2 B1 F2 -151.04(16) . . . . ? C4 N2 B1 F2 40.3(2) . . . . ? C2 N2 B1 F1 84.90(19) . . . . ? C4 N2 B1 F1 -83.8(2) . . . . ?