#------------------------------------------------------------------------------ #$Date: 2019-04-16 01:17:07 +0300 (Tue, 16 Apr 2019) $ #$Revision: 214638 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/08/1550886.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_1550886 loop_ _publ_author_name 'Boknevitz, Katherine' 'Italia, James S.' 'Li, Bo' 'Chatterjee, Abhishek' 'Liu, Shih-Yuan' _publ_section_title ; Synthesis and Characterization of an Unnatural Boron and Nitrogen-containing Tryptophan Analogue and its Incorporation into Proteins ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C8SC05167D _journal_year 2019 _chemical_formula_moiety '(C17 H31 B N3 O2 Si)+, (C F3 O3 S)-, 0.5(H2 O)' _chemical_formula_sum 'C18 H32 B F3 N3 O5.5 S Si' _chemical_formula_weight 506.42 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/6 _audit_update_record ; 2018-11-19 deposited with the CCDC. 2019-04-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.703(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.3865(16) _cell_length_b 6.5658(7) _cell_length_c 26.361(3) _cell_measurement_reflns_used 8831 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.09 _cell_measurement_theta_min 2.65 _cell_volume 2662.9(5) _computing_cell_refinement 'SAINT (Bruker, 2014)' _computing_data_collection 'APEX2 (Bruker, 2014)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2016/6 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker Kappa DUO CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_unetI/netI 0.0572 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 12645 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.296 _diffrn_reflns_theta_min 1.541 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description plate _exptl_crystal_F_000 1068 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.522 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.068 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 325 _refine_ls_number_reflns 6613 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.094 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0524 _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^)+(0.0769P)^2^+0.3206P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1414 _refine_ls_wR_factor_ref 0.1538 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4607 _reflns_number_total 6613 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8sc05167d2.cif _cod_data_source_block (C17H31BN3O2Si)+(CF3O3S)- _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_original_formula_sum 'C18 H32 B F3 N3 O5.50 S Si' _cod_database_code 1550886 _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 0.937 _shelx_estimated_absorpt_t_max 0.989 _shelx_res_file ; TITL twin in P2(1)/n twin.res created by SHELXL-2016/6 at 15:05:26 on 19-Nov-2018 CELL 0.71073 15.38650 6.56580 26.36110 90.0000 90.7027 90.0000 ZERR 4.00 0.00160 0.00070 0.00250 0.0000 0.0028 0.0000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H B N O Si S F UNIT 72 128 4 12 22 4 4 12 REM Old TITL sad in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.152, Rweak 0.006, Alpha 0.029, Orientation as input REM Formula found by SHELXT: C19 N5 O7 P2 L.S. 10 BOND $H FMAP 2 PLAN -5 SIZE 0.30 0.13 0.05 TEMP -173 DFIX 0.84 O1S H1OS O1S H2OS DANG 1.31 0.01 H1OS H2OS OMIT 4 0 2 OMIT -2 1 10 OMIT 5 1 9 OMIT 3 2 5 OMIT 1 2 5 OMIT 0 0 2 OMIT -3 0 13 OMIT -1 0 1 CONF EQIV $1 -x+1, -y+2, -z+1 HTAB N1 O2_$1 HTAB N1 O3 EQIV $2 -x+1, -y+1, -z+1 HTAB N1 O5_$2 HTAB N1 O4_$1 EQIV $3 -x+1, -y, -z HTAB O1S O1S_$3 ACTA REM ----Cation---- WGHT 0.076900 0.320600 FVAR 0.09232 0.80800 SI1 6 0.566358 0.444711 0.769286 11.00000 0.02261 0.01843 = 0.02675 -0.00062 0.00182 0.00018 O1 5 0.282861 1.012360 0.538855 11.00000 0.03095 0.05693 = 0.03823 0.01876 0.00353 0.01260 O2 5 0.420107 1.120284 0.524465 11.00000 0.03740 0.02861 = 0.02767 0.00611 0.00554 0.00662 N1 4 0.485956 0.764126 0.565280 11.00000 0.02957 0.02102 = 0.02106 0.00032 0.00289 0.00392 H1N 2 0.489420 0.724203 0.532647 11.00000 0.03480 H2N 2 0.506185 0.656408 0.582576 11.00000 0.04898 H3N 2 0.525539 0.864017 0.569794 11.00000 0.03096 N2 4 0.481083 0.528689 0.728936 11.00000 0.02495 0.01897 = 0.02007 0.00028 0.00326 -0.00280 N3 4 0.356031 0.565711 0.679262 11.00000 0.02428 0.02816 = 0.01864 -0.00314 0.00328 -0.00074 B1 3 0.399327 0.431426 0.716165 11.00000 0.02725 0.02314 = 0.01978 -0.00393 0.00465 0.00048 PART 1 C1 1 0.156177 1.216204 0.520680 21.00000 0.04738 0.07753 = 0.03999 0.01520 0.00707 0.02179 AFIX 33 H1A 2 0.132362 1.332947 0.501979 21.00000 -1.50000 H1B 2 0.125057 1.092260 0.510500 21.00000 -1.50000 H1C 2 0.149257 1.238338 0.557173 21.00000 -1.50000 AFIX 0 C2 1 0.251427 1.193209 0.508957 21.00000 0.03804 0.04443 = 0.03854 0.01546 -0.00025 0.01272 AFIX 23 H2A 2 0.259542 1.170345 0.472198 21.00000 -1.20000 H2B 2 0.283868 1.317181 0.519113 21.00000 -1.20000 AFIX 0 PART 2 SAME C1 C2 C1X 1 0.224646 1.323512 0.531498 -21.00000 0.04257 AFIX 33 H1X1 2 0.192937 1.423304 0.510734 -21.00000 -1.50000 H1X2 2 0.191644 1.294174 0.562208 -21.00000 -1.50000 H1X3 2 0.281713 1.378847 0.541005 -21.00000 -1.50000 AFIX 0 C2X 1 0.236320 1.131438 0.501794 -21.00000 0.03117 AFIX 23 H2X1 2 0.179923 1.068580 0.492343 -21.00000 -1.20000 H2X2 2 0.270973 1.154176 0.470909 -21.00000 -1.20000 AFIX 0 PART 0 C3 1 0.369078 1.002030 0.542964 11.00000 0.03356 0.03161 = 0.02056 -0.00002 0.00288 0.00831 C4 1 0.395405 0.826291 0.577622 11.00000 0.02605 0.02449 = 0.02236 0.00116 0.00037 0.00285 AFIX 13 H4 2 0.355062 0.708758 0.572074 11.00000 -1.20000 AFIX 0 C5 1 0.390397 0.898156 0.633264 11.00000 0.03439 0.02434 = 0.02078 -0.00025 0.00167 0.00450 AFIX 23 H5A 2 0.431351 1.012754 0.638496 11.00000 -1.20000 H5B 2 0.331035 0.949206 0.639793 11.00000 -1.20000 AFIX 0 C6 1 0.411667 0.732796 0.670598 11.00000 0.02991 0.02163 = 0.01981 -0.00130 0.00488 0.00002 C7 1 0.483569 0.707155 0.699574 11.00000 0.02859 0.02135 = 0.02164 -0.00135 0.00504 -0.00188 AFIX 43 H7 2 0.530948 0.799937 0.700099 11.00000 -1.20000 AFIX 0 C8 1 0.349404 0.242166 0.731795 11.00000 0.02864 0.02500 = 0.02536 -0.00287 0.00597 -0.00343 AFIX 43 H8 2 0.372896 0.146867 0.755358 11.00000 -1.20000 AFIX 0 C9 1 0.268290 0.216070 0.709997 11.00000 0.02880 0.03416 = 0.03259 -0.00784 0.01028 -0.00896 AFIX 43 H9 2 0.235468 0.099185 0.718938 11.00000 -1.20000 AFIX 0 C10 1 0.231471 0.357081 0.674566 11.00000 0.02276 0.05170 = 0.03060 -0.00791 0.00298 -0.00463 AFIX 43 H10 2 0.175214 0.331078 0.660794 11.00000 -1.20000 AFIX 0 C11 1 0.274938 0.528700 0.659877 11.00000 0.02327 0.04353 = 0.02454 -0.00286 0.00256 0.00333 AFIX 43 H11 2 0.248940 0.620992 0.636452 11.00000 -1.20000 AFIX 0 C12 1 0.584656 0.168603 0.755744 11.00000 0.03096 0.02005 = 0.04750 -0.00203 0.00427 0.00145 AFIX 137 H12A 2 0.534055 0.089924 0.766599 11.00000 -1.50000 H12B 2 0.636498 0.121659 0.774278 11.00000 -1.50000 H12C 2 0.593008 0.149503 0.719257 11.00000 -1.50000 AFIX 0 C13 1 0.666204 0.592885 0.754053 11.00000 0.02541 0.02730 = 0.03704 -0.00498 0.00340 -0.00155 AFIX 137 H13A 2 0.677711 0.582475 0.717663 11.00000 -1.50000 H13B 2 0.715744 0.537870 0.773337 11.00000 -1.50000 H13C 2 0.657587 0.736116 0.763160 11.00000 -1.50000 AFIX 0 C14 1 0.535460 0.484460 0.838171 11.00000 0.03039 0.03046 = 0.02412 0.00346 -0.00161 -0.00167 C15 1 0.526054 0.712878 0.848931 11.00000 0.03693 0.03162 = 0.02961 -0.00582 0.00369 0.00061 AFIX 137 H15A 2 0.507434 0.732638 0.884008 11.00000 -1.50000 H15B 2 0.482623 0.771464 0.825673 11.00000 -1.50000 H15C 2 0.582095 0.780505 0.843989 11.00000 -1.50000 AFIX 0 C16 1 0.608110 0.397412 0.873002 11.00000 0.04667 0.04726 = 0.03565 0.00832 -0.01185 0.00035 AFIX 137 H16A 2 0.663219 0.465264 0.865527 11.00000 -1.50000 H16B 2 0.613908 0.250779 0.866982 11.00000 -1.50000 H16C 2 0.593218 0.421060 0.908558 11.00000 -1.50000 AFIX 0 C17 1 0.449796 0.375758 0.850619 11.00000 0.03920 0.04116 = 0.02772 0.00366 0.00549 -0.00455 AFIX 137 H17A 2 0.455018 0.230496 0.842674 11.00000 -1.50000 H17B 2 0.402373 0.435170 0.830355 11.00000 -1.50000 H17C 2 0.437407 0.392338 0.886762 11.00000 -1.50000 AFIX 0 REM -----Anion-------- S1 7 0.395919 0.707202 0.420917 11.00000 0.02793 0.02089 = 0.02290 0.00097 -0.00080 0.00305 O3 5 0.401272 0.637256 0.472948 11.00000 0.03504 0.03327 = 0.02278 0.00083 -0.00294 -0.00002 O4 5 0.388844 0.925005 0.413929 11.00000 0.03998 0.02254 = 0.03898 0.00141 -0.00735 0.00392 O5 5 0.455267 0.606737 0.386934 11.00000 0.03959 0.03344 = 0.02744 0.00341 0.00547 0.01339 C18 1 0.289533 0.615442 0.399992 11.00000 0.03919 0.03688 = 0.03047 0.00630 -0.00429 -0.00381 F1 8 0.268796 0.681035 0.353295 11.00000 0.04617 0.04570 = 0.03187 0.00475 -0.01399 -0.00100 F2 8 0.288357 0.410663 0.398661 11.00000 0.07763 0.03939 = 0.05696 0.01362 -0.02731 -0.02457 F3 8 0.227050 0.677627 0.430884 11.00000 0.03033 0.10314 = 0.04739 0.00722 0.00520 -0.00011 REM -----Solvent water----- O1S 5 0.481078 0.218476 -0.000014 10.50000 0.12004 H1OS 2 0.479927 0.124058 0.024732 10.50000 -1.20000 H2OS 2 0.493161 0.124163 -0.024237 10.50000 -1.20000 HKLF 4 REM twin in P2(1)/n REM R1 = 0.0524 for 4607 Fo > 4sig(Fo) and 0.0829 for all 6613 data REM 325 parameters refined using 4 restraints END WGHT 0.0762 0.2742 REM Highest difference peak 0.522, deepest hole -0.636, 1-sigma level 0.068 Q1 1 0.4858 -0.0195 0.0375 11.00000 0.05 0.52 Q2 1 0.2585 0.4754 0.4202 11.00000 0.05 0.38 Q3 1 0.6163 0.5211 0.7600 11.00000 0.05 0.35 Q4 1 0.3401 0.6687 0.4060 11.00000 0.05 0.34 Q5 1 0.5545 0.4682 0.8124 11.00000 0.05 0.31 ; _shelx_res_checksum 3189 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.56636(4) 0.44471(10) 0.76929(2) 0.02258(16) Uani 1 1 d . . . . . O1 O 0.28286(12) 1.0124(3) 0.53886(7) 0.0420(5) Uani 1 1 d . . . . . O2 O 0.42011(11) 1.1203(3) 0.52447(6) 0.0312(4) Uani 1 1 d . . . . . N1 N 0.48596(14) 0.7641(3) 0.56528(8) 0.0239(4) Uani 1 1 d . . . . . H1N H 0.4894(17) 0.724(4) 0.5326(11) 0.035(7) Uiso 1 1 d . . . . . H2N H 0.506(2) 0.656(5) 0.5826(12) 0.049(9) Uiso 1 1 d . . . . . H3N H 0.5255(18) 0.864(4) 0.5698(10) 0.031(7) Uiso 1 1 d . . . . . N2 N 0.48108(12) 0.5287(3) 0.72894(6) 0.0213(4) Uani 1 1 d . . . . . N3 N 0.35603(12) 0.5657(3) 0.67926(6) 0.0237(4) Uani 1 1 d . . . . . B1 B 0.39933(17) 0.4314(4) 0.71616(9) 0.0234(5) Uani 1 1 d . . . . . C1 C 0.1562(3) 1.2162(7) 0.52068(14) 0.0549(14) Uani 0.808(8) 1 d D . P A 1 H1A H 0.132362 1.332947 0.501979 0.082 Uiso 0.808(8) 1 calc R U P A 1 H1B H 0.125057 1.092260 0.510500 0.082 Uiso 0.808(8) 1 calc R U P A 1 H1C H 0.149257 1.238338 0.557173 0.082 Uiso 0.808(8) 1 calc R U P A 1 C2 C 0.2514(3) 1.1932(9) 0.50896(19) 0.0403(12) Uani 0.808(8) 1 d D . P A 1 H2A H 0.259542 1.170345 0.472198 0.048 Uiso 0.808(8) 1 calc R U P A 1 H2B H 0.283868 1.317181 0.519113 0.048 Uiso 0.808(8) 1 calc R U P A 1 C1X C 0.2246(11) 1.324(2) 0.5315(6) 0.043(5) Uiso 0.192(8) 1 d D . P A 2 H1X1 H 0.192937 1.423304 0.510734 0.064 Uiso 0.192(8) 1 calc R U P A 2 H1X2 H 0.191644 1.294174 0.562208 0.064 Uiso 0.192(8) 1 calc R U P A 2 H1X3 H 0.281713 1.378847 0.541005 0.064 Uiso 0.192(8) 1 calc R U P A 2 C2X C 0.2363(16) 1.131(3) 0.5018(8) 0.031(5) Uiso 0.192(8) 1 d D . P A 2 H2X1 H 0.179923 1.068580 0.492343 0.037 Uiso 0.192(8) 1 calc R U P A 2 H2X2 H 0.270973 1.154176 0.470909 0.037 Uiso 0.192(8) 1 calc R U P A 2 C3 C 0.36908(16) 1.0020(4) 0.54296(8) 0.0286(5) Uani 1 1 d . . . . . C4 C 0.39541(15) 0.8263(4) 0.57762(8) 0.0243(5) Uani 1 1 d . . . . . H4 H 0.355062 0.708758 0.572074 0.029 Uiso 1 1 calc R U . . . C5 C 0.39040(16) 0.8982(4) 0.63326(8) 0.0265(5) Uani 1 1 d . . . . . H5A H 0.431351 1.012754 0.638496 0.032 Uiso 1 1 calc R U . . . H5B H 0.331035 0.949206 0.639793 0.032 Uiso 1 1 calc R U . . . C6 C 0.41167(15) 0.7328(4) 0.67060(8) 0.0237(5) Uani 1 1 d . . . . . C7 C 0.48357(15) 0.7072(4) 0.69957(8) 0.0238(5) Uani 1 1 d . . . . . H7 H 0.530948 0.799937 0.700099 0.029 Uiso 1 1 calc R U . . . C8 C 0.34940(16) 0.2422(4) 0.73179(9) 0.0263(5) Uani 1 1 d . . . . . H8 H 0.372896 0.146867 0.755358 0.032 Uiso 1 1 calc R U . . . C9 C 0.26829(16) 0.2161(4) 0.71000(9) 0.0318(6) Uani 1 1 d . . . . . H9 H 0.235468 0.099185 0.718938 0.038 Uiso 1 1 calc R U . . . C10 C 0.23147(16) 0.3571(5) 0.67457(9) 0.0350(6) Uani 1 1 d . . . . . H10 H 0.175214 0.331078 0.660794 0.042 Uiso 1 1 calc R U . . . C11 C 0.27494(15) 0.5287(4) 0.65988(8) 0.0304(6) Uani 1 1 d . . . . . H11 H 0.248940 0.620992 0.636452 0.037 Uiso 1 1 calc R U . . . C12 C 0.58466(17) 0.1686(4) 0.75574(10) 0.0328(6) Uani 1 1 d . . . . . H12A H 0.534055 0.089924 0.766599 0.049 Uiso 1 1 calc R U . . . H12B H 0.636498 0.121659 0.774278 0.049 Uiso 1 1 calc R U . . . H12C H 0.593008 0.149503 0.719257 0.049 Uiso 1 1 calc R U . . . C13 C 0.66620(15) 0.5929(4) 0.75405(9) 0.0299(5) Uani 1 1 d . . . . . H13A H 0.677711 0.582475 0.717663 0.045 Uiso 1 1 calc R U . . . H13B H 0.715744 0.537870 0.773337 0.045 Uiso 1 1 calc R U . . . H13C H 0.657587 0.736116 0.763160 0.045 Uiso 1 1 calc R U . . . C14 C 0.53546(16) 0.4845(4) 0.83817(8) 0.0283(5) Uani 1 1 d . . . . . C15 C 0.52605(18) 0.7129(4) 0.84893(9) 0.0327(6) Uani 1 1 d . . . . . H15A H 0.507434 0.732638 0.884008 0.049 Uiso 1 1 calc R U . . . H15B H 0.482623 0.771464 0.825673 0.049 Uiso 1 1 calc R U . . . H15C H 0.582095 0.780505 0.843989 0.049 Uiso 1 1 calc R U . . . C16 C 0.60811(19) 0.3974(5) 0.87300(10) 0.0433(7) Uani 1 1 d . . . . . H16A H 0.663219 0.465264 0.865527 0.065 Uiso 1 1 calc R U . . . H16B H 0.613908 0.250779 0.866982 0.065 Uiso 1 1 calc R U . . . H16C H 0.593218 0.421060 0.908558 0.065 Uiso 1 1 calc R U . . . C17 C 0.44980(17) 0.3758(5) 0.85062(9) 0.0360(6) Uani 1 1 d . . . . . H17A H 0.455018 0.230496 0.842674 0.054 Uiso 1 1 calc R U . . . H17B H 0.402373 0.435170 0.830355 0.054 Uiso 1 1 calc R U . . . H17C H 0.437407 0.392338 0.886762 0.054 Uiso 1 1 calc R U . . . S1 S 0.39592(4) 0.70720(9) 0.42092(2) 0.02392(15) Uani 1 1 d . . . . . O3 O 0.40127(11) 0.6373(3) 0.47295(6) 0.0304(4) Uani 1 1 d . . . . . O4 O 0.38884(12) 0.9250(3) 0.41393(6) 0.0339(4) Uani 1 1 d . . . . . O5 O 0.45527(11) 0.6067(3) 0.38693(6) 0.0335(4) Uani 1 1 d . . . . . C18 C 0.28953(18) 0.6154(4) 0.39999(9) 0.0356(6) Uani 1 1 d . . . . . F1 F 0.26880(10) 0.6810(3) 0.35329(5) 0.0414(4) Uani 1 1 d . . . . . F2 F 0.28836(13) 0.4107(3) 0.39866(7) 0.0582(5) Uani 1 1 d . . . . . F3 F 0.22705(11) 0.6776(3) 0.43088(7) 0.0602(6) Uani 1 1 d . . . . . O1S O 0.4811(6) 0.2185(12) 0.0000(3) 0.120(2) Uiso 0.5 1 d D . P . . H1OS H 0.480(7) 0.124(13) 0.025(3) 0.144 Uiso 0.5 1 d D U P . . H2OS H 0.493(7) 0.124(13) -0.024(3) 0.144 Uiso 0.5 1 d D U P . . 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 Si1 0.0226(3) 0.0184(3) 0.0267(3) -0.0006(3) 0.0018(2) 0.0002(3) O1 0.0310(10) 0.0569(14) 0.0382(10) 0.0188(9) 0.0035(8) 0.0126(9) O2 0.0374(10) 0.0286(10) 0.0277(8) 0.0061(7) 0.0055(7) 0.0066(8) N1 0.0296(12) 0.0210(11) 0.0211(10) 0.0003(8) 0.0029(8) 0.0039(9) N2 0.0249(10) 0.0190(10) 0.0201(9) 0.0003(7) 0.0033(7) -0.0028(8) N3 0.0243(10) 0.0282(11) 0.0186(9) -0.0031(8) 0.0033(7) -0.0007(8) B1 0.0273(14) 0.0231(14) 0.0198(11) -0.0039(10) 0.0047(9) 0.0005(11) C1 0.047(3) 0.078(3) 0.040(2) 0.015(2) 0.0071(16) 0.022(2) C2 0.038(3) 0.044(3) 0.039(2) 0.015(2) -0.0002(18) 0.013(2) C3 0.0336(14) 0.0316(14) 0.0206(11) 0.0000(10) 0.0029(9) 0.0083(11) C4 0.0261(12) 0.0245(13) 0.0224(11) 0.0012(9) 0.0004(9) 0.0029(10) C5 0.0344(13) 0.0243(13) 0.0208(10) -0.0003(9) 0.0017(9) 0.0045(10) C6 0.0299(13) 0.0216(12) 0.0198(10) -0.0013(9) 0.0049(9) 0.0000(10) C7 0.0286(12) 0.0213(12) 0.0216(10) -0.0013(9) 0.0050(9) -0.0019(10) C8 0.0286(13) 0.0250(13) 0.0254(11) -0.0029(9) 0.0060(9) -0.0034(10) C9 0.0288(13) 0.0342(15) 0.0326(13) -0.0078(11) 0.0103(10) -0.0090(11) C10 0.0228(13) 0.0517(18) 0.0306(13) -0.0079(12) 0.0030(10) -0.0046(12) C11 0.0233(12) 0.0435(16) 0.0245(11) -0.0029(11) 0.0026(9) 0.0033(11) C12 0.0310(14) 0.0201(13) 0.0475(15) -0.0020(11) 0.0043(11) 0.0015(10) C13 0.0254(13) 0.0273(14) 0.0370(13) -0.0050(11) 0.0034(10) -0.0015(10) C14 0.0304(13) 0.0305(14) 0.0241(11) 0.0035(10) -0.0016(9) -0.0017(10) C15 0.0369(14) 0.0316(15) 0.0296(12) -0.0058(11) 0.0037(10) 0.0006(12) C16 0.0467(17) 0.0473(19) 0.0356(14) 0.0083(13) -0.0118(12) 0.0004(14) C17 0.0392(15) 0.0412(17) 0.0277(12) 0.0037(11) 0.0055(10) -0.0045(13) S1 0.0279(3) 0.0209(3) 0.0229(3) 0.0010(2) -0.0008(2) 0.0030(2) O3 0.0350(10) 0.0333(10) 0.0228(8) 0.0008(7) -0.0029(7) 0.0000(8) O4 0.0400(11) 0.0225(10) 0.0390(10) 0.0014(8) -0.0073(8) 0.0039(8) O5 0.0396(10) 0.0334(11) 0.0274(8) 0.0034(7) 0.0055(7) 0.0134(8) C18 0.0392(15) 0.0369(16) 0.0305(13) 0.0063(11) -0.0043(10) -0.0038(12) F1 0.0462(10) 0.0457(11) 0.0319(8) 0.0047(7) -0.0140(7) -0.0010(8) F2 0.0776(13) 0.0394(11) 0.0570(11) 0.0136(9) -0.0273(9) -0.0246(10) F3 0.0303(9) 0.1031(17) 0.0474(10) 0.0072(10) 0.0052(7) -0.0001(10) 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' 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' Si Si 0.0817 0.0704 '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' F F 0.0171 0.0103 '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 N2 Si1 C13 108.36(11) N2 Si1 C12 107.46(11) C13 Si1 C12 109.76(12) N2 Si1 C14 109.85(10) C13 Si1 C14 110.50(11) C12 Si1 C14 110.83(12) C3 O1 C2 113.4(3) C4 N1 H1N 110.7(18) C4 N1 H2N 115(2) H1N N1 H2N 103(3) C4 N1 H3N 113.8(18) H1N N1 H3N 107(2) H2N N1 H3N 106(3) C7 N2 B1 105.63(19) C7 N2 Si1 124.52(16) B1 N2 Si1 129.75(16) C11 N3 C6 129.2(2) C11 N3 B1 123.2(2) C6 N3 B1 107.64(19) N2 B1 N3 106.0(2) N2 B1 C8 137.6(2) N3 B1 C8 116.4(2) C2 C1 H1A 109.5 C2 C1 H1B 109.5 H1A C1 H1B 109.5 C2 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 O1 C2 C1 106.2(3) O1 C2 H2A 110.5 C1 C2 H2A 110.5 O1 C2 H2B 110.5 C1 C2 H2B 110.5 H2A C2 H2B 108.7 O2 C3 O1 125.8(2) O2 C3 C4 123.9(2) O1 C3 C4 110.2(2) N1 C4 C3 108.58(18) N1 C4 C5 110.40(19) C3 C4 C5 108.80(19) N1 C4 H4 109.7 C3 C4 H4 109.7 C5 C4 H4 109.7 C6 C5 C4 112.9(2) C6 C5 H5A 109.0 C4 C5 H5A 109.0 C6 C5 H5B 109.0 C4 C5 H5B 109.0 H5A C5 H5B 107.8 C7 C6 N3 107.8(2) C7 C6 C5 129.3(2) N3 C6 C5 122.8(2) C6 C7 N2 112.9(2) C6 C7 H7 123.6 N2 C7 H7 123.6 C9 C8 B1 116.5(2) C9 C8 H8 121.7 B1 C8 H8 121.7 C8 C9 C10 122.8(2) C8 C9 H9 118.6 C10 C9 H9 118.6 C11 C10 C9 121.9(2) C11 C10 H10 119.1 C9 C10 H10 119.1 N3 C11 C10 119.2(2) N3 C11 H11 120.4 C10 C11 H11 120.4 Si1 C12 H12A 109.5 Si1 C12 H12B 109.5 H12A C12 H12B 109.5 Si1 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 Si1 C13 H13A 109.5 Si1 C13 H13B 109.5 H13A C13 H13B 109.5 Si1 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C15 C14 C17 109.3(2) C15 C14 C16 108.7(2) C17 C14 C16 108.5(2) C15 C14 Si1 109.65(16) C17 C14 Si1 111.42(17) C16 C14 Si1 109.20(18) C14 C15 H15A 109.5 C14 C15 H15B 109.5 H15A C15 H15B 109.5 C14 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 C14 C17 H17A 109.5 C14 C17 H17B 109.5 H17A C17 H17B 109.5 C14 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 O4 S1 O5 114.79(11) O4 S1 O3 115.96(11) O5 S1 O3 114.40(10) O4 S1 C18 102.85(12) O5 S1 C18 103.49(12) O3 S1 C18 102.84(11) F3 C18 F1 107.3(2) F3 C18 F2 108.2(2) F1 C18 F2 107.1(2) F3 C18 S1 111.46(19) F1 C18 S1 112.01(18) F2 C18 S1 110.5(2) H1OS O1S H2OS 93(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Si1 N2 1.767(2) Si1 C13 1.866(2) Si1 C12 1.870(3) Si1 C14 1.901(2) O1 C3 1.331(3) O1 C2 1.502(5) O2 C3 1.211(3) N1 C4 1.492(3) N1 H1N 0.90(3) N1 H2N 0.90(3) N1 H3N 0.90(3) N2 C7 1.405(3) N2 B1 1.447(3) N3 C11 1.364(3) N3 C6 1.412(3) N3 B1 1.467(3) B1 C8 1.520(4) C1 C2 1.509(6) C1 H1A 0.9800 C1 H1B 0.9800 C1 H1C 0.9800 C2 H2A 0.9900 C2 H2B 0.9900 C3 C4 1.524(3) C4 C5 1.544(3) C4 H4 1.0000 C5 C6 1.499(3) C5 H5A 0.9900 C5 H5B 0.9900 C6 C7 1.347(3) C7 H7 0.9500 C8 C9 1.378(3) C8 H8 0.9500 C9 C10 1.427(4) C9 H9 0.9500 C10 C11 1.369(4) C10 H10 0.9500 C11 H11 0.9500 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C14 C15 1.534(4) C14 C17 1.538(4) C14 C16 1.547(4) 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 0.9800 C17 H17B 0.9800 C17 H17C 0.9800 S1 O4 1.4458(19) S1 O5 1.4462(17) S1 O3 1.4478(17) S1 C18 1.823(3) C18 F3 1.332(3) C18 F1 1.339(3) C18 F2 1.345(3) O1S H1OS 0.90(2) O1S H2OS 0.91(2) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O2 0.90(3) 2.30(3) 2.889(3) 123(2) 3_676 N1 H1N O3 0.90(3) 2.14(3) 2.870(3) 137(2) . N1 H2N O5 0.90(3) 1.99(3) 2.882(3) 172(3) 3_666 N1 H3N O4 0.90(3) 1.96(3) 2.855(3) 175(2) 3_676 O1S H2OS O1S 0.91(2) 2.37(10) 2.927(16) 119(8) 3_655 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 C13 Si1 N2 C7 -13.7(2) C12 Si1 N2 C7 -132.23(18) C14 Si1 N2 C7 107.12(18) C13 Si1 N2 B1 162.08(19) C12 Si1 N2 B1 43.5(2) C14 Si1 N2 B1 -77.1(2) C7 N2 B1 N3 -1.1(2) Si1 N2 B1 N3 -177.45(14) C7 N2 B1 C8 -178.5(3) Si1 N2 B1 C8 5.2(4) C11 N3 B1 N2 -177.09(19) C6 N3 B1 N2 0.8(2) C11 N3 B1 C8 0.9(3) C6 N3 B1 C8 178.87(18) C3 O1 C2 C1 -163.9(3) C2 O1 C3 O2 -1.3(4) C2 O1 C3 C4 174.9(3) O2 C3 C4 N1 -26.8(3) O1 C3 C4 N1 157.0(2) O2 C3 C4 C5 93.4(3) O1 C3 C4 C5 -82.8(2) N1 C4 C5 C6 -63.3(3) C3 C4 C5 C6 177.6(2) C11 N3 C6 C7 177.5(2) B1 N3 C6 C7 -0.3(2) C11 N3 C6 C5 -4.8(3) B1 N3 C6 C5 177.48(19) C4 C5 C6 C7 106.6(3) C4 C5 C6 N3 -70.6(3) N3 C6 C7 N2 -0.5(2) C5 C6 C7 N2 -178.0(2) B1 N2 C7 C6 1.0(2) Si1 N2 C7 C6 177.61(15) N2 B1 C8 C9 176.8(3) N3 B1 C8 C9 -0.4(3) B1 C8 C9 C10 -0.1(3) C8 C9 C10 C11 0.0(4) C6 N3 C11 C10 -178.5(2) B1 N3 C11 C10 -1.0(3) C9 C10 C11 N3 0.5(4) O4 S1 C18 F3 -66.6(2) O5 S1 C18 F3 173.61(19) O3 S1 C18 F3 54.2(2) O4 S1 C18 F1 53.7(2) O5 S1 C18 F1 -66.1(2) O3 S1 C18 F1 174.52(19) O4 S1 C18 F2 173.04(18) O5 S1 C18 F2 53.2(2) O3 S1 C18 F2 -66.1(2)