#------------------------------------------------------------------------------ #$Date: 2016-08-07 11:19:29 +0300 (Sun, 07 Aug 2016) $ #$Revision: 185213 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225207.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_7225207 loop_ _publ_author_name 'Surov, Artem O.' 'Solanko, Katarzyna A.' 'Bond, Andrew D.' 'Bauer-Brandl, Annette' 'Perlovich, German L.' _publ_section_title ; Cocrystals of the antiandrogenic drug bicalutamide: screening, crystal structures, formation thermodynamics and lattice energies ; _journal_issue 25 _journal_name_full CrystEngComm _journal_page_first 4818 _journal_paper_doi 10.1039/C6CE00931J _journal_volume 18 _journal_year 2016 _chemical_formula_moiety 'C18 H14 F4 N2 O4 S, C7 H7 N O' _chemical_formula_sum 'C25 H21 F4 N3 O5 S' _chemical_formula_weight 551.51 _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 mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2016-04-15 deposited with the CCDC. 2016-05-11 downloaded from the CCDC. ; _cell_angle_alpha 101.978(7) _cell_angle_beta 97.828(7) _cell_angle_gamma 90.114(8) _cell_formula_units_Z 2 _cell_length_a 5.7985(11) _cell_length_b 11.964(3) _cell_length_c 17.496(3) _cell_measurement_reflns_used 3211 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 24.98 _cell_measurement_theta_min 2.31 _cell_volume 1175.7(4) _computing_cell_refinement 'SAINT (Bruker, 2014)' _computing_data_collection 'APEX2 (Bruker, 2014)' _computing_data_reduction SAINT _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material SHELXL _computing_structure_refinement 'SHELXL (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measurement_device_type 'Bruker X8-APEXII CCD' _diffrn_measurement_method '\w and \f-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_unetI/netI 0.0668 _diffrn_reflns_Laue_measured_fraction_full 0.969 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 4022 _diffrn_reflns_point_group_measured_fraction_full 0.969 _diffrn_reflns_point_group_measured_fraction_max 0.969 _diffrn_reflns_theta_full 25.091 _diffrn_reflns_theta_max 25.091 _diffrn_reflns_theta_min 3.548 _diffrn_source sealed-tube _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2014)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.558 _exptl_crystal_description plate _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.383 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.081 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 353 _refine_ls_number_reflns 4022 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.125 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0536 _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^)+2.6631P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1214 _refine_ls_wR_factor_ref 0.1308 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2925 _reflns_number_total 4022 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00931j2.cif _cod_data_source_block BIC_BZA _cod_depositor_comments 'Adding full bibliography for 7225207--7225208.cif.' _cod_database_code 7225207 _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 0.954 _shelx_estimated_absorpt_t_max 0.996 _shelx_res_file ; BIC_BZA.res created by SHELXL-2014/7 TITL BIC_BZA in P-1 CELL 0.71073 5.7985 11.964 17.496 101.978 97.828 90.114 ZERR 2.00 0.0011 0.003 0.003 0.007 0.007 0.008 LATT 1 SFAC C H N O F S UNIT 50 42 6 10 8 2 SIZE 0.22 0.16 0.02 TEMP -123 MERG 0 L.S. 10 ACTA BOND $H CONF LIST 4 FMAP 2 PLAN -5 SHEL 5.8 0 WGHT 0.000000 2.663100 BASF 0.17826 FVAR 10.90647 S1 6 0.939767 0.634688 0.114929 11.00000 0.02232 0.02169 = 0.01847 0.00268 0.00124 -0.00061 F1 5 1.285884 1.123085 0.498402 11.00000 0.03334 0.05029 = 0.02152 0.01403 0.00142 -0.00056 F2 5 1.471301 1.247089 0.455745 11.00000 0.02714 0.03605 = 0.03437 0.00227 -0.00603 -0.01067 F4 5 1.134379 0.885431 0.439881 11.00000 0.04843 0.04398 = 0.01901 -0.00409 0.00109 -0.00902 F3 5 1.522526 1.068073 0.415024 11.00000 0.02701 0.04617 = 0.02838 -0.00143 -0.00398 0.01240 O1 4 0.835679 0.849557 0.032284 11.00000 0.02180 0.02725 = 0.01822 -0.00001 -0.00434 0.00705 H1 2 0.795841 0.821349 -0.016963 11.00000 0.06336 O2 4 1.342226 0.902522 0.173164 11.00000 0.02245 0.03372 = 0.02545 -0.00236 -0.00365 0.00587 O3 4 0.694532 0.641458 0.087859 11.00000 0.01969 0.03964 = 0.02153 0.00557 -0.00102 -0.00707 O4 4 1.030807 0.521985 0.109688 11.00000 0.04016 0.01861 = 0.02798 0.00669 0.00407 0.00163 O5 4 0.278690 0.250725 0.117435 11.00000 0.04449 0.03656 = 0.02348 -0.00227 0.00042 -0.01775 N1 3 0.957537 1.359485 0.507768 11.00000 0.03245 0.03385 = 0.02582 -0.00318 0.00151 -0.00356 N2 3 0.985032 0.983152 0.162772 11.00000 0.01891 0.02307 = 0.01776 -0.00037 -0.00298 0.00528 H2 2 0.860819 0.980788 0.130400 11.00000 0.02563 N3 3 0.487184 0.385217 0.082037 11.00000 0.02998 0.03869 = 0.01764 0.00041 0.00314 -0.00456 AFIX 93 H11 2 0.458134 0.352404 0.031683 11.00000 -1.20000 H12 2 0.573625 0.448547 0.097099 11.00000 -1.20000 AFIX 0 C1 1 1.110715 0.704283 0.060333 11.00000 0.02007 0.02648 = 0.01349 -0.00089 0.00282 0.00459 AFIX 23 H8 2 1.276089 0.698546 0.082012 11.00000 -1.20000 H9 2 1.089430 0.659462 0.005398 11.00000 -1.20000 AFIX 0 C2 1 1.070941 0.829788 0.056481 11.00000 0.01853 0.02236 = 0.01539 0.00204 0.00161 0.00441 C3 1 1.228381 0.862273 0.000604 11.00000 0.02585 0.02225 = 0.02460 0.00506 0.00252 0.00277 AFIX 137 H3 2 1.188663 0.813173 -0.051922 11.00000 -1.50000 H4 2 1.391434 0.852118 0.020756 11.00000 -1.50000 H5 2 1.205919 0.942341 -0.002823 11.00000 -1.50000 AFIX 0 C4 1 1.147988 0.909111 0.137849 11.00000 0.01974 0.02000 = 0.02204 0.00652 0.00124 0.00083 C5 1 0.992881 1.061674 0.234652 11.00000 0.01898 0.01802 = 0.01695 0.00202 0.00280 0.00152 C6 1 0.806638 1.133121 0.244996 11.00000 0.02495 0.02225 = 0.01544 0.00634 -0.00230 0.00131 AFIX 43 H6 2 0.681881 1.129743 0.203232 11.00000 -1.20000 AFIX 0 C7 1 0.802087 1.208993 0.315692 11.00000 0.02208 0.01931 = 0.02288 0.00408 0.00407 0.00564 AFIX 43 H7 2 0.674731 1.258310 0.321982 11.00000 -1.20000 AFIX 0 C8 1 0.980368 1.214378 0.377656 11.00000 0.01847 0.01841 = 0.01669 0.00089 0.00155 -0.00056 C9 1 1.167180 1.141445 0.367336 11.00000 0.02051 0.02151 = 0.01745 0.00635 0.00067 -0.00198 C10 1 1.175358 1.066534 0.296107 11.00000 0.01604 0.01921 = 0.02369 0.00638 0.00121 0.00606 AFIX 43 H10 2 1.304596 1.018646 0.289086 11.00000 -1.20000 AFIX 0 C11 1 0.969017 1.294904 0.450861 11.00000 0.01725 0.02203 = 0.02165 0.00151 0.00048 -0.00434 C12 1 1.360550 1.143740 0.433649 11.00000 0.02015 0.02933 = 0.01870 0.00313 0.00327 -0.00116 C13 1 0.993315 0.709086 0.213934 11.00000 0.02331 0.01988 = 0.01822 0.00321 0.00340 -0.00108 C14 1 1.201784 0.691871 0.258877 11.00000 0.02281 0.02313 = 0.02605 0.00437 0.00048 0.00179 AFIX 43 H14 2 1.310895 0.640107 0.236746 11.00000 -1.20000 AFIX 0 C15 1 1.247596 0.750730 0.335643 11.00000 0.02695 0.02341 = 0.02879 0.01193 -0.00431 -0.00137 AFIX 43 H15 2 1.388721 0.740701 0.367736 11.00000 -1.20000 AFIX 0 C16 1 1.084706 0.824420 0.364950 11.00000 0.03349 0.02544 = 0.01712 0.00590 0.00622 -0.00947 C17 1 0.876029 0.840635 0.322281 11.00000 0.02187 0.03151 = 0.02426 0.00411 0.00954 0.00476 AFIX 43 H17 2 0.765536 0.890438 0.345500 11.00000 -1.20000 AFIX 0 C18 1 0.830303 0.782759 0.244657 11.00000 0.01876 0.02652 = 0.02168 0.00446 0.00221 -0.00004 AFIX 43 H18 2 0.688969 0.793463 0.212909 11.00000 -1.20000 AFIX 0 C19 1 0.459621 0.398690 0.219890 11.00000 0.01859 0.01729 = 0.01813 0.00404 0.00017 0.00506 C20 1 0.666392 0.461984 0.247299 11.00000 0.02179 0.02273 = 0.01804 0.00791 0.00362 0.00075 AFIX 43 H20 2 0.774367 0.467930 0.211974 11.00000 -1.20000 AFIX 0 C21 1 0.715725 0.516397 0.325828 11.00000 0.02701 0.02366 = 0.02725 0.00498 -0.00149 -0.00550 AFIX 43 H21 2 0.858192 0.558731 0.344674 11.00000 -1.20000 AFIX 0 C22 1 0.556308 0.508772 0.376729 11.00000 0.03188 0.02704 = 0.01892 0.00109 -0.00155 0.00368 AFIX 43 H22 2 0.588737 0.546679 0.430570 11.00000 -1.20000 AFIX 0 C23 1 0.349742 0.446140 0.349534 11.00000 0.02674 0.02822 = 0.02477 0.01134 0.00866 0.00479 AFIX 43 H23 2 0.239945 0.442215 0.384614 11.00000 -1.20000 AFIX 0 C24 1 0.302616 0.389469 0.271843 11.00000 0.01641 0.02295 = 0.02176 0.00260 0.00161 0.00152 AFIX 43 H24 2 0.163338 0.344243 0.253817 11.00000 -1.20000 AFIX 0 C25 1 0.400483 0.339114 0.135353 11.00000 0.01963 0.02561 = 0.02157 0.00237 -0.00011 0.00424 HKLF 5 REM BIC_BZA in P-1 REM R1 = 0.0536 for 2925 Fo > 4sig(Fo) and 0.0828 for all 4022 data REM 353 parameters refined using 0 restraints END WGHT 0.0000 2.6630 REM Highest difference peak 0.383, deepest hole -0.380, 1-sigma level 0.081 Q1 1 0.9537 0.6818 0.1721 11.00000 0.05 0.38 Q2 1 0.7269 1.0986 0.1169 11.00000 0.05 0.34 Q3 1 0.9230 0.5565 0.1319 11.00000 0.05 0.33 Q4 1 0.8646 0.4787 0.1409 11.00000 0.05 0.32 Q5 1 0.6007 0.4846 0.0095 11.00000 0.05 0.32 ; _shelx_res_checksum 84309 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 0.93977(18) 0.63469(9) 0.11493(6) 0.0212(3) Uani 1 1 d . . F1 F 1.2859(4) 1.1231(2) 0.49840(14) 0.0343(7) Uani 1 1 d . . F2 F 1.4713(4) 1.2471(2) 0.45575(15) 0.0343(6) Uani 1 1 d . . F4 F 1.1344(5) 0.8854(2) 0.43988(14) 0.0391(7) Uani 1 1 d . . F3 F 1.5225(4) 1.0681(2) 0.41502(14) 0.0359(7) Uani 1 1 d . . O1 O 0.8357(5) 0.8496(2) 0.03228(18) 0.0238(7) Uani 1 1 d . . H1 H 0.796(10) 0.821(5) -0.017(3) 0.063(19) Uiso 1 1 d . . O2 O 1.3422(5) 0.9025(3) 0.17316(17) 0.0291(7) Uani 1 1 d . . O3 O 0.6945(5) 0.6415(3) 0.08786(16) 0.0275(7) Uani 1 1 d . . O4 O 1.0308(5) 0.5220(2) 0.10969(17) 0.0287(7) Uani 1 1 d . . O5 O 0.2787(6) 0.2507(3) 0.11744(17) 0.0365(8) Uani 1 1 d . . N1 N 0.9575(6) 1.3595(3) 0.5078(2) 0.0323(9) Uani 1 1 d . . N2 N 0.9850(6) 0.9832(3) 0.1628(2) 0.0211(8) Uani 1 1 d . . H2 H 0.861(8) 0.981(4) 0.130(3) 0.026(12) Uiso 1 1 d . . N3 N 0.4872(6) 0.3852(3) 0.0820(2) 0.0296(9) Uani 1 1 d . . H11 H 0.4581 0.3524 0.0317 0.036 Uiso 1 1 calc R U H12 H 0.5736 0.4485 0.0971 0.036 Uiso 1 1 calc R U C1 C 1.1107(7) 0.7043(3) 0.0603(2) 0.0207(9) Uani 1 1 d . . H8 H 1.2761 0.6985 0.0820 0.025 Uiso 1 1 calc R U H9 H 1.0894 0.6595 0.0054 0.025 Uiso 1 1 calc R U C2 C 1.0709(7) 0.8298(3) 0.0565(2) 0.0191(9) Uani 1 1 d . . C3 C 1.2284(7) 0.8623(4) 0.0006(2) 0.0243(10) Uani 1 1 d . . H3 H 1.1887 0.8132 -0.0519 0.036 Uiso 1 1 calc R U H4 H 1.3914 0.8521 0.0208 0.036 Uiso 1 1 calc R U H5 H 1.2059 0.9423 -0.0028 0.036 Uiso 1 1 calc R U C4 C 1.1480(7) 0.9091(3) 0.1378(2) 0.0204(9) Uani 1 1 d . . C5 C 0.9929(7) 1.0617(3) 0.2347(2) 0.0182(9) Uani 1 1 d . . C6 C 0.8066(7) 1.1331(3) 0.2450(2) 0.0210(9) Uani 1 1 d . . H6 H 0.6819 1.1297 0.2032 0.025 Uiso 1 1 calc R U C7 C 0.8021(7) 1.2090(3) 0.3157(2) 0.0214(9) Uani 1 1 d . . H7 H 0.6747 1.2583 0.3220 0.026 Uiso 1 1 calc R U C8 C 0.9804(7) 1.2144(3) 0.3777(2) 0.0183(9) Uani 1 1 d . . C9 C 1.1672(7) 1.1414(3) 0.3673(2) 0.0197(9) Uani 1 1 d . . C10 C 1.1754(7) 1.0665(3) 0.2961(2) 0.0195(9) Uani 1 1 d . . H10 H 1.3046 1.0186 0.2891 0.023 Uiso 1 1 calc R U C11 C 0.9690(7) 1.2949(4) 0.4509(2) 0.0210(9) Uani 1 1 d . . C12 C 1.3605(7) 1.1437(4) 0.4336(2) 0.0230(10) Uani 1 1 d . . C13 C 0.9933(7) 0.7091(3) 0.2139(2) 0.0205(9) Uani 1 1 d . . C14 C 1.2018(7) 0.6919(4) 0.2589(2) 0.0244(10) Uani 1 1 d . . H14 H 1.3109 0.6401 0.2367 0.029 Uiso 1 1 calc R U C15 C 1.2476(8) 0.7507(4) 0.3356(3) 0.0262(10) Uani 1 1 d . . H15 H 1.3887 0.7407 0.3677 0.031 Uiso 1 1 calc R U C16 C 1.0847(8) 0.8244(4) 0.3650(2) 0.0249(10) Uani 1 1 d . . C17 C 0.8760(7) 0.8406(4) 0.3223(2) 0.0255(10) Uani 1 1 d . . H17 H 0.7655 0.8904 0.3455 0.031 Uiso 1 1 calc R U C18 C 0.8303(7) 0.7828(4) 0.2447(2) 0.0225(10) Uani 1 1 d . . H18 H 0.6890 0.7935 0.2129 0.027 Uiso 1 1 calc R U C19 C 0.4596(7) 0.3987(3) 0.2199(2) 0.0182(9) Uani 1 1 d . . C20 C 0.6664(7) 0.4620(3) 0.2473(2) 0.0202(9) Uani 1 1 d . . H20 H 0.7744 0.4679 0.2120 0.024 Uiso 1 1 calc R U C21 C 0.7157(7) 0.5164(4) 0.3258(2) 0.0265(10) Uani 1 1 d . . H21 H 0.8582 0.5587 0.3447 0.032 Uiso 1 1 calc R U C22 C 0.5563(7) 0.5088(4) 0.3767(2) 0.0270(10) Uani 1 1 d . . H22 H 0.5887 0.5467 0.4306 0.032 Uiso 1 1 calc R U C23 C 0.3497(7) 0.4461(4) 0.3495(2) 0.0252(10) Uani 1 1 d . . H23 H 0.2399 0.4422 0.3846 0.030 Uiso 1 1 calc R U C24 C 0.3026(7) 0.3895(3) 0.2718(2) 0.0208(9) Uani 1 1 d . . H24 H 0.1633 0.3442 0.2538 0.025 Uiso 1 1 calc R U C25 C 0.4005(7) 0.3391(4) 0.1354(2) 0.0229(10) 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 0.0223(6) 0.0217(6) 0.0185(5) 0.0027(4) 0.0012(4) -0.0006(4) F1 0.0333(15) 0.0503(18) 0.0215(14) 0.0140(12) 0.0014(11) -0.0006(12) F2 0.0271(14) 0.0361(16) 0.0344(15) 0.0023(12) -0.0060(11) -0.0107(12) F4 0.0484(17) 0.0440(17) 0.0190(14) -0.0041(12) 0.0011(12) -0.0090(13) F3 0.0270(14) 0.0462(17) 0.0284(14) -0.0014(12) -0.0040(11) 0.0124(12) O1 0.0218(16) 0.0273(18) 0.0182(16) 0.0000(13) -0.0043(13) 0.0071(13) O2 0.0224(17) 0.0337(19) 0.0255(16) -0.0024(14) -0.0036(13) 0.0059(13) O3 0.0197(16) 0.0396(19) 0.0215(16) 0.0056(14) -0.0010(12) -0.0071(13) O4 0.0402(18) 0.0186(16) 0.0280(17) 0.0067(13) 0.0041(14) 0.0016(13) O5 0.044(2) 0.037(2) 0.0235(17) -0.0023(14) 0.0004(15) -0.0177(16) N1 0.032(2) 0.034(2) 0.026(2) -0.0032(19) 0.0015(17) -0.0036(18) N2 0.019(2) 0.023(2) 0.0178(19) -0.0004(15) -0.0030(16) 0.0053(15) N3 0.030(2) 0.039(2) 0.0176(19) 0.0004(17) 0.0031(16) -0.0046(17) C1 0.020(2) 0.026(2) 0.013(2) -0.0009(17) 0.0028(17) 0.0046(18) C2 0.019(2) 0.022(2) 0.015(2) 0.0020(17) 0.0016(17) 0.0044(17) C3 0.026(2) 0.022(2) 0.025(2) 0.0051(19) 0.0025(18) 0.0028(18) C4 0.020(2) 0.020(2) 0.022(2) 0.0065(18) 0.0012(18) 0.0008(18) C5 0.019(2) 0.018(2) 0.017(2) 0.0020(17) 0.0028(17) 0.0015(17) C6 0.025(2) 0.022(2) 0.015(2) 0.0063(17) -0.0023(17) 0.0013(18) C7 0.022(2) 0.019(2) 0.023(2) 0.0041(18) 0.0041(18) 0.0056(18) C8 0.018(2) 0.018(2) 0.017(2) 0.0009(17) 0.0015(16) -0.0006(17) C9 0.021(2) 0.022(2) 0.017(2) 0.0064(18) 0.0007(17) -0.0020(17) C10 0.016(2) 0.019(2) 0.024(2) 0.0064(18) 0.0012(17) 0.0061(17) C11 0.017(2) 0.022(2) 0.022(2) 0.0015(19) 0.0005(17) -0.0043(17) C12 0.020(2) 0.029(3) 0.019(2) 0.0031(19) 0.0033(18) -0.0012(19) C13 0.023(2) 0.020(2) 0.018(2) 0.0032(18) 0.0034(17) -0.0011(18) C14 0.023(2) 0.023(2) 0.026(2) 0.0044(19) 0.0005(18) 0.0018(18) C15 0.027(2) 0.023(2) 0.029(3) 0.012(2) -0.0043(19) -0.0014(19) C16 0.033(3) 0.025(3) 0.017(2) 0.0059(18) 0.0062(19) -0.009(2) C17 0.022(2) 0.032(3) 0.024(2) 0.004(2) 0.0095(19) 0.0048(19) C18 0.019(2) 0.027(2) 0.022(2) 0.0045(19) 0.0022(17) 0.0000(18) C19 0.019(2) 0.017(2) 0.018(2) 0.0040(17) 0.0002(17) 0.0051(17) C20 0.022(2) 0.023(2) 0.018(2) 0.0079(18) 0.0036(17) 0.0007(18) C21 0.027(2) 0.024(3) 0.027(2) 0.0050(19) -0.0015(19) -0.0055(19) C22 0.032(3) 0.027(3) 0.019(2) 0.0011(19) -0.0016(19) 0.004(2) C23 0.027(2) 0.028(3) 0.025(2) 0.011(2) 0.0087(19) 0.0048(19) C24 0.016(2) 0.023(2) 0.022(2) 0.0026(18) 0.0016(17) 0.0015(17) C25 0.020(2) 0.026(3) 0.022(2) 0.0024(19) -0.0001(18) 0.0042(19) 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 O4 S1 O3 116.74(18) O4 S1 C13 108.74(19) O3 S1 C13 107.70(18) O4 S1 C1 105.40(18) O3 S1 C1 110.73(18) C13 S1 C1 107.14(19) C2 O1 H1 111(4) C4 N2 C5 128.7(4) C4 N2 H2 115(3) C5 N2 H2 116(3) C25 N3 H11 120.0 C25 N3 H12 120.0 H11 N3 H12 120.0 C2 C1 S1 120.1(3) C2 C1 H8 107.3 S1 C1 H8 107.3 C2 C1 H9 107.3 S1 C1 H9 107.3 H8 C1 H9 106.9 O1 C2 C3 111.4(3) O1 C2 C1 112.1(3) C3 C2 C1 108.0(3) O1 C2 C4 108.2(3) C3 C2 C4 106.1(3) C1 C2 C4 110.8(3) C2 C3 H3 109.5 C2 C3 H4 109.5 H3 C3 H4 109.5 C2 C3 H5 109.5 H3 C3 H5 109.5 H4 C3 H5 109.5 O2 C4 N2 125.7(4) O2 C4 C2 120.3(4) N2 C4 C2 114.0(3) C6 C5 C10 119.8(4) C6 C5 N2 117.9(4) C10 C5 N2 122.2(4) C7 C6 C5 120.2(4) C7 C6 H6 119.9 C5 C6 H6 119.9 C6 C7 C8 120.9(4) C6 C7 H7 119.5 C8 C7 H7 119.5 C7 C8 C9 118.8(4) C7 C8 C11 119.3(4) C9 C8 C11 121.9(4) C10 C9 C8 120.6(4) C10 C9 C12 119.2(4) C8 C9 C12 120.1(4) C9 C10 C5 119.6(4) C9 C10 H10 120.2 C5 C10 H10 120.2 N1 C11 C8 178.8(5) F3 C12 F1 107.0(3) F3 C12 F2 106.4(3) F1 C12 F2 105.8(3) F3 C12 C9 112.9(3) F1 C12 C9 112.7(3) F2 C12 C9 111.5(3) C18 C13 C14 121.9(4) C18 C13 S1 119.8(3) C14 C13 S1 118.4(3) C15 C14 C13 119.0(4) C15 C14 H14 120.5 C13 C14 H14 120.5 C14 C15 C16 118.4(4) C14 C15 H15 120.8 C16 C15 H15 120.8 F4 C16 C17 118.3(4) F4 C16 C15 118.1(4) C17 C16 C15 123.6(4) C16 C17 C18 118.3(4) C16 C17 H17 120.9 C18 C17 H17 120.9 C13 C18 C17 118.9(4) C13 C18 H18 120.6 C17 C18 H18 120.6 C20 C19 C24 119.7(4) C20 C19 C25 121.7(4) C24 C19 C25 118.6(4) C21 C20 C19 120.3(4) C21 C20 H20 119.9 C19 C20 H20 119.9 C22 C21 C20 119.6(4) C22 C21 H21 120.2 C20 C21 H21 120.2 C21 C22 C23 120.3(4) C21 C22 H22 119.9 C23 C22 H22 119.9 C24 C23 C22 120.3(4) C24 C23 H23 119.8 C22 C23 H23 119.8 C23 C24 C19 119.8(4) C23 C24 H24 120.1 C19 C24 H24 120.1 O5 C25 N3 122.6(4) O5 C25 C19 120.4(4) N3 C25 C19 117.1(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O4 1.439(3) S1 O3 1.444(3) S1 C13 1.761(4) S1 C1 1.781(4) F1 C12 1.335(5) F2 C12 1.350(5) F4 C16 1.354(5) F3 C12 1.331(5) O1 C2 1.408(5) O1 H1 0.86(6) O2 C4 1.220(5) O5 C25 1.231(5) N1 C11 1.137(5) N2 C4 1.350(5) N2 C5 1.400(5) N2 H2 0.85(4) N3 C25 1.329(5) N3 H11 0.8800 N3 H12 0.8800 C1 C2 1.533(6) C1 H8 0.9900 C1 H9 0.9900 C2 C3 1.530(6) C2 C4 1.546(5) C3 H3 0.9800 C3 H4 0.9800 C3 H5 0.9800 C5 C6 1.386(5) C5 C10 1.394(5) C6 C7 1.378(5) C6 H6 0.9500 C7 C8 1.383(5) C7 H7 0.9500 C8 C9 1.400(6) C8 C11 1.444(6) C9 C10 1.382(5) C9 C12 1.495(6) C10 H10 0.9500 C13 C18 1.380(6) C13 C14 1.390(6) C14 C15 1.371(6) C14 H14 0.9500 C15 C16 1.371(6) C15 H15 0.9500 C16 C17 1.369(6) C17 C18 1.380(6) C17 H17 0.9500 C18 H18 0.9500 C19 C20 1.389(5) C19 C24 1.391(5) C19 C25 1.496(5) C20 C21 1.384(6) C20 H20 0.9500 C21 C22 1.383(6) C21 H21 0.9500 C22 C23 1.384(6) C22 H22 0.9500 C23 C24 1.378(6) C23 H23 0.9500 C24 H24 0.9500 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 O4 S1 C1 C2 -176.8(3) O3 S1 C1 C2 56.0(3) C13 S1 C1 C2 -61.1(3) S1 C1 C2 O1 -52.5(4) S1 C1 C2 C3 -175.6(3) S1 C1 C2 C4 68.6(4) C5 N2 C4 O2 -4.7(7) C5 N2 C4 C2 176.3(4) O1 C2 C4 O2 175.6(4) C3 C2 C4 O2 -64.7(5) C1 C2 C4 O2 52.3(5) O1 C2 C4 N2 -5.3(5) C3 C2 C4 N2 114.4(4) C1 C2 C4 N2 -128.6(4) C4 N2 C5 C6 176.8(4) C4 N2 C5 C10 -5.8(7) C10 C5 C6 C7 0.2(6) N2 C5 C6 C7 177.6(4) C5 C6 C7 C8 -0.8(6) C6 C7 C8 C9 0.2(6) C6 C7 C8 C11 -179.9(4) C7 C8 C9 C10 1.0(6) C11 C8 C9 C10 -178.9(4) C7 C8 C9 C12 -178.9(4) C11 C8 C9 C12 1.2(6) C8 C9 C10 C5 -1.6(6) C12 C9 C10 C5 178.3(4) C6 C5 C10 C9 1.0(6) N2 C5 C10 C9 -176.3(4) C10 C9 C12 F3 -1.1(5) C8 C9 C12 F3 178.8(4) C10 C9 C12 F1 -122.5(4) C8 C9 C12 F1 57.4(5) C10 C9 C12 F2 118.7(4) C8 C9 C12 F2 -61.4(5) O4 S1 C13 C18 -143.2(3) O3 S1 C13 C18 -15.8(4) C1 S1 C13 C18 103.3(4) O4 S1 C13 C14 37.2(4) O3 S1 C13 C14 164.6(3) C1 S1 C13 C14 -76.2(4) C18 C13 C14 C15 -0.7(6) S1 C13 C14 C15 178.9(3) C13 C14 C15 C16 0.0(6) C14 C15 C16 F4 -177.7(4) C14 C15 C16 C17 1.5(7) F4 C16 C17 C18 176.8(4) C15 C16 C17 C18 -2.4(7) C14 C13 C18 C17 -0.1(6) S1 C13 C18 C17 -179.7(3) C16 C17 C18 C13 1.6(6) C24 C19 C20 C21 -0.4(6) C25 C19 C20 C21 179.8(4) C19 C20 C21 C22 -0.9(6) C20 C21 C22 C23 0.7(6) C21 C22 C23 C24 1.0(6) C22 C23 C24 C19 -2.3(6) C20 C19 C24 C23 2.1(6) C25 C19 C24 C23 -178.2(4) C20 C19 C25 O5 150.1(4) C24 C19 C25 O5 -29.6(6) C20 C19 C25 N3 -29.1(6) C24 C19 C25 N3 151.2(4)