#------------------------------------------------------------------------------ #$Date: 2016-05-12 06:06:11 +0300 (Thu, 12 May 2016) $ #$Revision: 182892 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225208.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_7225208 loop_ _publ_author_name 'Surov, Artem Olegovich' 'Solanko, Katarzyna' 'Bond, Andrew David' 'Bauer-Brandl, Annette' 'Perlovich, German L.' _publ_section_title ; Cocrystals of the Antiandrogenic Drug Bicalutamide: Screening, Crystal Structures, Formation Thermodynamics and Lattice Energies ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C6CE00931J _journal_year 2016 _chemical_formula_moiety 'C18 H14 F4 N2 O4 S, C7 H7 N O2' _chemical_formula_sum 'C25 H21 F4 N3 O6 S' _chemical_formula_weight 567.51 _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 _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 90 _cell_angle_beta 97.821(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.8888(3) _cell_length_b 21.5969(11) _cell_length_c 19.2814(10) _cell_measurement_reflns_used 9917 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 24.95 _cell_measurement_theta_min 2.33 _cell_volume 2429.4(2) _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 0.887 _diffrn_measured_fraction_theta_max 0.887 _diffrn_measurement_device_type 'Bruker D8-QUEST PHOTON-100' _diffrn_measurement_method '\w and \f-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_unetI/netI 0.0227 _diffrn_reflns_Laue_measured_fraction_full 0.887 _diffrn_reflns_Laue_measured_fraction_max 0.887 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9776 _diffrn_reflns_point_group_measured_fraction_full 0.887 _diffrn_reflns_point_group_measured_fraction_max 0.887 _diffrn_reflns_theta_full 25.012 _diffrn_reflns_theta_max 25.012 _diffrn_reflns_theta_min 3.544 _diffrn_source 'Incoatec I\mS Cu microsource' _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6196 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2014)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.552 _exptl_crystal_description block _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.252 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 373 _refine_ls_number_reflns 3786 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0300 _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^)+(0.0316P)^2^+1.1943P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.0741 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3210 _reflns_number_total 3786 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00931j2.cif _cod_data_source_block BIC_2OHBZA _cod_database_code 7225208 _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 0.963 _shelx_estimated_absorpt_t_max 0.975 _shelx_res_file ; ks1140.res created by SHELXL-2014/7 TITL ks1140 in P2(1)/n CELL 0.71073 5.8888 21.5969 19.2814 90.000 97.821 90.000 ZERR 4.00 0.0003 0.0011 0.0010 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O F S UNIT 100 84 12 24 16 4 SIZE 0.18 0.12 0.12 TEMP -123 L.S. 10 ACTA BOND $H CONF LIST 4 FMAP 2 PLAN -10 SHEL 5.8 0 WGHT 0.031600 1.194300 FVAR 0.10430 S1 6 0.574628 0.010269 0.375961 11.00000 0.02609 0.02532 = 0.01914 -0.00147 0.00036 0.00445 F1 5 0.153550 0.068178 -0.039158 11.00000 0.03986 0.05173 = 0.03792 -0.02300 0.00285 -0.00945 F2 5 -0.046876 0.150377 -0.036336 11.00000 0.02856 0.06482 = 0.02980 0.00582 -0.00659 0.00116 F3 5 -0.070692 0.078526 0.038887 11.00000 0.03738 0.06519 = 0.02690 -0.00289 0.00169 -0.02707 F4 5 0.405784 -0.029234 0.075185 11.00000 0.04990 0.05544 = 0.01946 -0.00525 0.00144 -0.00111 O1 4 0.619673 0.157887 0.370929 11.00000 0.02364 0.03382 = 0.01767 -0.00118 0.00019 -0.00934 H1 2 0.654224 0.162390 0.416362 11.00000 0.04571 O2 4 0.132938 0.108118 0.257487 11.00000 0.02417 0.04286 = 0.02328 0.00200 -0.00013 -0.01050 O3 4 0.808199 0.030724 0.394308 11.00000 0.02218 0.04633 = 0.02807 -0.01138 -0.00370 0.00763 O4 4 0.507483 -0.044131 0.411389 11.00000 0.05387 0.02649 = 0.02430 0.00453 0.00555 0.00505 N1 3 0.437082 0.187814 -0.108393 11.00000 0.04226 0.05671 = 0.02302 0.00244 0.00094 -0.01587 N2 3 0.469097 0.155104 0.241628 11.00000 0.02159 0.02426 = 0.01501 -0.00075 -0.00100 -0.00578 H2 2 0.588408 0.169266 0.265257 11.00000 0.02251 C1 1 0.380487 0.069447 0.393890 11.00000 0.01990 0.02593 = 0.01879 -0.00099 0.00465 -0.00043 AFIX 23 H8 2 0.223212 0.053504 0.380082 11.00000 -1.20000 H9 2 0.399920 0.075561 0.445243 11.00000 -1.20000 AFIX 0 C2 1 0.394295 0.133595 0.359897 11.00000 0.01951 0.02396 = 0.01996 -0.00120 0.00223 -0.00232 C3 1 0.226147 0.176674 0.389777 11.00000 0.03227 0.02833 = 0.02446 0.00171 0.00563 0.00650 AFIX 137 H3 2 0.235424 0.218126 0.369675 11.00000 -1.50000 H4 2 0.265132 0.178931 0.440771 11.00000 -1.50000 H5 2 0.070008 0.160605 0.378056 11.00000 -1.50000 AFIX 0 C4 1 0.318336 0.130114 0.280669 11.00000 0.02145 0.01919 = 0.02120 0.00045 0.00281 -0.00004 C5 1 0.450238 0.160341 0.168621 11.00000 0.02408 0.01711 = 0.01830 -0.00062 0.00181 0.00156 C6 1 0.618775 0.193744 0.141194 11.00000 0.02620 0.02514 = 0.02028 -0.00270 0.00072 -0.00590 AFIX 43 H6 2 0.740389 0.212207 0.171662 11.00000 -1.20000 AFIX 0 C7 1 0.609549 0.200081 0.069937 11.00000 0.02943 0.02542 = 0.02311 -0.00166 0.00499 -0.00897 AFIX 43 H7 2 0.724519 0.223379 0.051554 11.00000 -1.20000 AFIX 0 C8 1 0.434513 0.172910 0.024362 11.00000 0.02663 0.02414 = 0.01859 -0.00042 0.00262 0.00027 C9 1 0.266228 0.138711 0.052273 11.00000 0.02123 0.02202 = 0.02080 -0.00131 0.00123 0.00151 C10 1 0.273232 0.132898 0.123768 11.00000 0.02262 0.02162 = 0.02247 0.00141 0.00363 -0.00272 AFIX 43 H10 2 0.157354 0.110180 0.142421 11.00000 -1.20000 AFIX 0 C11 1 0.432701 0.180666 -0.049759 11.00000 0.02862 0.03105 = 0.02439 -0.00044 0.00089 -0.00725 C12 1 0.076461 0.108691 0.004317 11.00000 0.02691 0.04101 = 0.02156 -0.00076 0.00234 -0.00399 C13 1 0.528225 -0.002995 0.285242 11.00000 0.02216 0.01975 = 0.02093 -0.00120 0.00264 0.00316 C14 1 0.333438 -0.035167 0.256771 11.00000 0.02606 0.02604 = 0.02586 0.00113 0.00503 -0.00322 AFIX 43 H14 2 0.229256 -0.050710 0.286069 11.00000 -1.20000 AFIX 0 C15 1 0.293403 -0.044233 0.185296 11.00000 0.02866 0.02774 = 0.02816 -0.00405 -0.00225 -0.00566 AFIX 43 H15 2 0.160657 -0.065742 0.164486 11.00000 -1.20000 AFIX 0 C16 1 0.448838 -0.021606 0.144989 11.00000 0.03244 0.02961 = 0.01812 -0.00232 0.00119 0.00559 C17 1 0.645167 0.009227 0.172218 11.00000 0.02715 0.02924 = 0.02763 0.00282 0.01025 0.00296 AFIX 43 H17 2 0.750563 0.023487 0.142606 11.00000 -1.20000 AFIX 0 C18 1 0.685653 0.019002 0.243770 11.00000 0.02121 0.02471 = 0.02643 -0.00234 0.00202 -0.00012 AFIX 43 H18 2 0.819105 0.040432 0.264180 11.00000 -1.20000 AFIX 0 N3 3 0.987764 0.097823 0.526855 11.00000 0.03727 0.04382 = 0.01679 -0.00425 0.00027 0.01300 H11 2 0.948788 0.085158 0.483673 11.00000 0.03812 H12 2 1.087598 0.076261 0.552762 11.00000 0.06022 O5 4 0.701503 0.166229 0.512184 11.00000 0.03191 0.04127 = 0.02034 0.00170 -0.00372 0.00872 O6 4 0.536141 0.209474 0.617927 11.00000 0.02900 0.04189 = 0.02887 -0.00281 0.00010 0.01354 H13 2 0.550442 0.200417 0.576465 11.00000 0.04158 C19 1 0.897394 0.155347 0.627152 11.00000 0.02260 0.01886 = 0.01877 0.00051 0.00293 -0.00266 C20 1 1.097574 0.138109 0.670464 11.00000 0.02398 0.02256 = 0.02320 -0.00067 0.00268 -0.00029 AFIX 43 H20 2 1.214016 0.116354 0.650962 11.00000 -1.20000 AFIX 0 C21 1 1.129031 0.152028 0.740640 11.00000 0.02940 0.02776 = 0.02332 -0.00001 -0.00410 -0.00125 AFIX 43 H21 2 1.266974 0.140601 0.769214 11.00000 -1.20000 AFIX 0 C22 1 0.957837 0.182871 0.769368 11.00000 0.04110 0.02722 = 0.01923 -0.00477 0.00248 -0.00402 AFIX 43 H22 2 0.977908 0.191858 0.818050 11.00000 -1.20000 AFIX 0 C23 1 0.758919 0.200666 0.728228 11.00000 0.03069 0.02465 = 0.02773 -0.00447 0.00795 0.00008 AFIX 43 H23 2 0.641778 0.221259 0.748642 11.00000 -1.20000 AFIX 0 C24 1 0.729830 0.188479 0.656939 11.00000 0.02306 0.02038 = 0.02449 0.00043 0.00203 -0.00091 C25 1 0.857675 0.139945 0.552033 11.00000 0.02278 0.02467 = 0.02034 0.00207 0.00384 -0.00394 HKLF 4 REM ks1140 in P2(1)/n REM R1 = 0.0300 for 3210 Fo > 4sig(Fo) and 0.0389 for all 3786 data REM 373 parameters refined using 0 restraints END WGHT 0.0315 1.1973 REM Highest difference peak 0.252, deepest hole -0.291, 1-sigma level 0.038 Q1 1 0.5508 0.0072 0.3209 11.00000 0.05 0.25 Q2 1 0.3190 0.1650 0.0382 11.00000 0.05 0.21 Q3 1 0.7944 0.1579 0.6407 11.00000 0.05 0.18 Q4 1 0.4776 0.0464 0.3866 11.00000 0.05 0.18 Q5 1 0.8818 0.1387 0.5976 11.00000 0.05 0.17 Q6 1 0.6176 -0.0073 0.2761 11.00000 0.05 0.17 Q7 1 0.5421 0.1691 0.0431 11.00000 0.05 0.17 Q8 1 0.3188 -0.0118 0.1655 11.00000 0.05 0.16 Q9 1 1.0085 0.1577 0.6381 11.00000 0.05 0.16 Q10 1 0.2373 0.1503 0.0833 11.00000 0.05 0.16 ; _shelx_res_checksum 60377 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 S1 S 0.57463(7) 0.01027(2) 0.37596(2) 0.02377(13) Uani 1 1 d . . F1 F 0.15355(19) 0.06818(6) -0.03916(6) 0.0434(3) Uani 1 1 d . . F2 F -0.04688(18) 0.15038(6) -0.03634(6) 0.0420(3) Uani 1 1 d . . F3 F -0.07069(19) 0.07853(6) 0.03889(6) 0.0434(3) Uani 1 1 d . . F4 F 0.4058(2) -0.02923(6) 0.07519(5) 0.0419(3) Uani 1 1 d . . O1 O 0.6197(2) 0.15789(6) 0.37093(7) 0.0253(3) Uani 1 1 d . . H1 H 0.654(4) 0.1624(10) 0.4164(12) 0.046(7) Uiso 1 1 d . . O2 O 0.1329(2) 0.10812(6) 0.25749(6) 0.0304(3) Uani 1 1 d . . O3 O 0.8082(2) 0.03072(6) 0.39431(7) 0.0329(3) Uani 1 1 d . . O4 O 0.5075(2) -0.04413(6) 0.41139(7) 0.0349(3) Uani 1 1 d . . N1 N 0.4371(3) 0.18781(9) -0.10839(9) 0.0410(4) Uani 1 1 d . . N2 N 0.4691(3) 0.15510(7) 0.24163(7) 0.0206(3) Uani 1 1 d . . H2 H 0.588(3) 0.1693(9) 0.2653(10) 0.023(5) Uiso 1 1 d . . C1 C 0.3805(3) 0.06945(8) 0.39389(9) 0.0214(4) Uani 1 1 d . . H8 H 0.2232 0.0535 0.3801 0.026 Uiso 1 1 calc R U H9 H 0.3999 0.0756 0.4452 0.026 Uiso 1 1 calc R U C2 C 0.3943(3) 0.13360(8) 0.35990(9) 0.0212(4) Uani 1 1 d . . C3 C 0.2261(3) 0.17667(9) 0.38978(10) 0.0282(4) Uani 1 1 d . . H3 H 0.2354 0.2181 0.3697 0.042 Uiso 1 1 calc R U H4 H 0.2651 0.1789 0.4408 0.042 Uiso 1 1 calc R U H5 H 0.0700 0.1606 0.3781 0.042 Uiso 1 1 calc R U C4 C 0.3183(3) 0.13011(8) 0.28067(9) 0.0206(4) Uani 1 1 d . . C5 C 0.4502(3) 0.16034(8) 0.16862(9) 0.0199(4) Uani 1 1 d . . C6 C 0.6188(3) 0.19374(8) 0.14119(9) 0.0241(4) Uani 1 1 d . . H6 H 0.7404 0.2122 0.1717 0.029 Uiso 1 1 calc R U C7 C 0.6095(3) 0.20008(8) 0.06994(9) 0.0259(4) Uani 1 1 d . . H7 H 0.7245 0.2234 0.0516 0.031 Uiso 1 1 calc R U C8 C 0.4345(3) 0.17291(8) 0.02436(9) 0.0232(4) Uani 1 1 d . . C9 C 0.2662(3) 0.13871(8) 0.05227(9) 0.0215(4) Uani 1 1 d . . C10 C 0.2732(3) 0.13290(8) 0.12377(9) 0.0222(4) Uani 1 1 d . . H10 H 0.1574 0.1102 0.1424 0.027 Uiso 1 1 calc R U C11 C 0.4327(3) 0.18067(9) -0.04976(10) 0.0283(4) Uani 1 1 d . . C12 C 0.0765(3) 0.10869(9) 0.00432(10) 0.0299(5) Uani 1 1 d . . C13 C 0.5282(3) -0.00299(8) 0.28524(9) 0.0210(4) Uani 1 1 d . . C14 C 0.3334(3) -0.03517(8) 0.25677(9) 0.0258(4) Uani 1 1 d . . H14 H 0.2293 -0.0507 0.2861 0.031 Uiso 1 1 calc R U C15 C 0.2934(3) -0.04423(9) 0.18530(10) 0.0288(4) Uani 1 1 d . . H15 H 0.1607 -0.0657 0.1645 0.035 Uiso 1 1 calc R U C16 C 0.4488(3) -0.02161(9) 0.14499(9) 0.0269(4) Uani 1 1 d . . C17 C 0.6452(3) 0.00923(9) 0.17222(10) 0.0274(4) Uani 1 1 d . . H17 H 0.7506 0.0235 0.1426 0.033 Uiso 1 1 calc R U C18 C 0.6857(3) 0.01900(8) 0.24377(9) 0.0242(4) Uani 1 1 d . . H18 H 0.8191 0.0404 0.2642 0.029 Uiso 1 1 calc R U N3 N 0.9878(3) 0.09782(8) 0.52685(10) 0.0329(4) Uani 1 1 d . . H11 H 0.949(3) 0.0852(10) 0.4837(12) 0.038(6) Uiso 1 1 d . . H12 H 1.088(4) 0.0763(12) 0.5528(13) 0.060(8) Uiso 1 1 d . . O5 O 0.7015(2) 0.16623(6) 0.51218(6) 0.0318(3) Uani 1 1 d . . O6 O 0.5361(2) 0.20947(6) 0.61793(8) 0.0336(3) Uani 1 1 d . . H13 H 0.550(4) 0.2004(10) 0.5765(12) 0.042(7) Uiso 1 1 d . . C19 C 0.8974(3) 0.15535(8) 0.62715(9) 0.0201(4) Uani 1 1 d . . C20 C 1.0976(3) 0.13811(8) 0.67046(9) 0.0233(4) Uani 1 1 d . . H20 H 1.2140 0.1164 0.6510 0.028 Uiso 1 1 calc R U C21 C 1.1290(3) 0.15203(8) 0.74064(9) 0.0275(4) Uani 1 1 d . . H21 H 1.2670 0.1406 0.7692 0.033 Uiso 1 1 calc R U C22 C 0.9578(3) 0.18287(9) 0.76937(10) 0.0293(4) Uani 1 1 d . . H22 H 0.9779 0.1919 0.8180 0.035 Uiso 1 1 calc R U C23 C 0.7589(3) 0.20067(8) 0.72823(10) 0.0273(4) Uani 1 1 d . . H23 H 0.6418 0.2213 0.7486 0.033 Uiso 1 1 calc R U C24 C 0.7298(3) 0.18848(8) 0.65694(9) 0.0228(4) Uani 1 1 d . . C25 C 0.8577(3) 0.13994(8) 0.55203(9) 0.0225(4) 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 0.0261(3) 0.0253(2) 0.0191(2) -0.00147(19) 0.00036(18) 0.00445(19) F1 0.0399(7) 0.0517(8) 0.0379(7) -0.0230(6) 0.0028(5) -0.0094(6) F2 0.0286(6) 0.0648(8) 0.0298(7) 0.0058(6) -0.0066(5) 0.0012(6) F3 0.0374(7) 0.0652(8) 0.0269(6) -0.0029(6) 0.0017(5) -0.0271(6) F4 0.0499(7) 0.0554(8) 0.0195(6) -0.0052(5) 0.0014(5) -0.0011(6) O1 0.0236(7) 0.0338(7) 0.0177(7) -0.0012(6) 0.0002(5) -0.0093(6) O2 0.0242(7) 0.0429(8) 0.0233(7) 0.0020(6) -0.0001(5) -0.0105(6) O3 0.0222(7) 0.0463(8) 0.0281(7) -0.0114(6) -0.0037(5) 0.0076(6) O4 0.0539(9) 0.0265(7) 0.0243(7) 0.0045(6) 0.0056(6) 0.0050(6) N1 0.0423(11) 0.0567(12) 0.0230(10) 0.0024(9) 0.0009(8) -0.0159(9) N2 0.0216(8) 0.0243(8) 0.0150(8) -0.0008(6) -0.0010(7) -0.0058(7) C1 0.0199(9) 0.0259(10) 0.0188(9) -0.0010(8) 0.0046(7) -0.0004(7) C2 0.0195(9) 0.0240(10) 0.0200(9) -0.0012(7) 0.0022(7) -0.0023(7) C3 0.0323(11) 0.0283(11) 0.0245(10) 0.0017(8) 0.0056(8) 0.0065(8) C4 0.0215(10) 0.0192(9) 0.0212(10) 0.0004(7) 0.0028(8) 0.0000(8) C5 0.0241(9) 0.0171(9) 0.0183(10) -0.0006(7) 0.0018(7) 0.0016(7) C6 0.0262(10) 0.0251(10) 0.0203(10) -0.0027(8) 0.0007(8) -0.0059(8) C7 0.0294(10) 0.0254(10) 0.0231(10) -0.0017(8) 0.0050(8) -0.0090(8) C8 0.0266(10) 0.0241(10) 0.0186(10) -0.0004(8) 0.0026(8) 0.0003(8) C9 0.0212(9) 0.0220(9) 0.0208(10) -0.0013(8) 0.0012(7) 0.0015(7) C10 0.0226(9) 0.0216(9) 0.0225(10) 0.0014(8) 0.0036(8) -0.0027(8) C11 0.0286(11) 0.0311(11) 0.0244(12) -0.0004(9) 0.0009(8) -0.0073(8) C12 0.0269(10) 0.0410(12) 0.0216(10) -0.0008(9) 0.0023(8) -0.0040(9) C13 0.0222(9) 0.0198(9) 0.0209(10) -0.0012(7) 0.0026(7) 0.0032(7) C14 0.0261(10) 0.0260(10) 0.0259(10) 0.0011(8) 0.0050(8) -0.0032(8) C15 0.0287(10) 0.0277(11) 0.0282(11) -0.0041(8) -0.0023(8) -0.0057(8) C16 0.0324(11) 0.0296(11) 0.0181(10) -0.0023(8) 0.0012(8) 0.0056(8) C17 0.0271(10) 0.0292(10) 0.0276(10) 0.0028(8) 0.0103(8) 0.0030(8) C18 0.0212(9) 0.0247(10) 0.0264(10) -0.0023(8) 0.0020(8) -0.0001(8) N3 0.0373(10) 0.0438(11) 0.0168(9) -0.0042(8) 0.0003(8) 0.0130(9) O5 0.0319(7) 0.0413(8) 0.0203(7) 0.0017(6) -0.0037(6) 0.0087(6) O6 0.0290(8) 0.0419(9) 0.0289(8) -0.0028(7) 0.0001(6) 0.0135(6) C19 0.0226(9) 0.0189(9) 0.0188(9) 0.0005(7) 0.0029(7) -0.0027(7) C20 0.0240(10) 0.0226(9) 0.0232(10) -0.0007(8) 0.0027(8) -0.0003(8) C21 0.0294(10) 0.0278(10) 0.0233(10) 0.0000(8) -0.0041(8) -0.0013(8) C22 0.0411(12) 0.0272(10) 0.0192(10) -0.0048(8) 0.0025(9) -0.0040(9) C23 0.0307(11) 0.0247(10) 0.0277(11) -0.0045(8) 0.0080(8) 0.0001(8) C24 0.0231(10) 0.0204(9) 0.0245(10) 0.0004(8) 0.0020(8) -0.0009(7) C25 0.0228(9) 0.0247(10) 0.0203(10) 0.0021(8) 0.0038(8) -0.0039(8) 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 116.58(8) O4 S1 C13 108.87(8) O3 S1 C13 107.95(8) O4 S1 C1 105.57(8) O3 S1 C1 110.41(8) C13 S1 C1 107.07(8) C2 O1 H1 106.0(14) C4 N2 C5 128.55(15) C4 N2 H2 114.0(13) C5 N2 H2 117.4(13) C2 C1 S1 119.41(12) C2 C1 H8 107.5 S1 C1 H8 107.5 C2 C1 H9 107.5 S1 C1 H9 107.5 H8 C1 H9 107.0 O1 C2 C3 111.11(14) O1 C2 C4 107.94(13) C3 C2 C4 106.82(14) O1 C2 C1 111.85(14) C3 C2 C1 108.24(14) C4 C2 C1 110.78(14) 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 125.09(16) O2 C4 C2 120.64(15) N2 C4 C2 114.22(15) C6 C5 C10 119.86(16) C6 C5 N2 117.48(15) C10 C5 N2 122.66(15) C7 C6 C5 119.96(16) C7 C6 H6 120.0 C5 C6 H6 120.0 C6 C7 C8 120.99(16) C6 C7 H7 119.5 C8 C7 H7 119.5 C7 C8 C9 118.83(16) C7 C8 C11 118.94(16) C9 C8 C11 122.24(16) C10 C9 C8 120.36(16) C10 C9 C12 119.74(15) C8 C9 C12 119.90(15) C9 C10 C5 119.99(16) C9 C10 H10 120.0 C5 C10 H10 120.0 N1 C11 C8 178.0(2) F3 C12 F1 107.08(16) F3 C12 F2 106.45(15) F1 C12 F2 106.07(15) F3 C12 C9 112.59(15) F1 C12 C9 112.52(15) F2 C12 C9 111.69(16) C18 C13 C14 121.61(16) C18 C13 S1 119.49(13) C14 C13 S1 118.91(13) C15 C14 C13 119.04(17) C15 C14 H14 120.5 C13 C14 H14 120.5 C16 C15 C14 118.66(17) C16 C15 H15 120.7 C14 C15 H15 120.7 F4 C16 C15 118.34(16) F4 C16 C17 118.39(16) C15 C16 C17 123.27(17) C16 C17 C18 118.45(17) C16 C17 H17 120.8 C18 C17 H17 120.8 C17 C18 C13 118.96(16) C17 C18 H18 120.5 C13 C18 H18 120.5 C25 N3 H11 118.2(13) C25 N3 H12 123.1(17) H11 N3 H12 117(2) C24 O6 H13 105.4(15) C20 C19 C24 118.27(16) C20 C19 C25 122.33(16) C24 C19 C25 119.40(15) C21 C20 C19 121.29(17) C21 C20 H20 119.4 C19 C20 H20 119.4 C20 C21 C22 119.42(17) C20 C21 H21 120.3 C22 C21 H21 120.3 C23 C22 C21 120.81(17) C23 C22 H22 119.6 C21 C22 H22 119.6 C22 C23 C24 119.91(17) C22 C23 H23 120.0 C24 C23 H23 120.0 O6 C24 C23 117.86(16) O6 C24 C19 121.91(16) C23 C24 C19 120.22(16) O5 C25 N3 120.02(17) O5 C25 C19 120.41(16) N3 C25 C19 119.57(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O4 1.4411(13) S1 O3 1.4421(13) S1 C13 1.7568(17) S1 C1 1.7798(17) F1 C12 1.333(2) F2 C12 1.341(2) F3 C12 1.333(2) F4 C16 1.345(2) O1 C2 1.416(2) O1 H1 0.88(2) O2 C4 1.218(2) N1 C11 1.145(2) N2 C4 1.352(2) N2 C5 1.401(2) N2 H2 0.841(19) C1 C2 1.539(2) C1 H8 0.9900 C1 H9 0.9900 C2 C3 1.528(2) C2 C4 1.534(2) C3 H3 0.9800 C3 H4 0.9800 C3 H5 0.9800 C5 C6 1.389(2) C5 C10 1.393(2) C6 C7 1.374(2) C6 H6 0.9500 C7 C8 1.390(2) C7 H7 0.9500 C8 C9 1.401(2) C8 C11 1.438(3) C9 C10 1.379(2) C9 C12 1.498(2) C10 H10 0.9500 C13 C18 1.388(2) C13 C14 1.389(2) C14 C15 1.380(3) C14 H14 0.9500 C15 C16 1.369(3) C15 H15 0.9500 C16 C17 1.375(3) C17 C18 1.384(3) C17 H17 0.9500 C18 H18 0.9500 N3 C25 1.323(2) N3 H11 0.88(2) N3 H12 0.86(3) O5 C25 1.251(2) O6 C24 1.356(2) O6 H13 0.84(2) C19 C20 1.399(2) C19 C24 1.403(2) C19 C25 1.473(2) C20 C21 1.374(2) C20 H20 0.9500 C21 C22 1.385(3) C21 H21 0.9500 C22 C23 1.377(3) C22 H22 0.9500 C23 C24 1.387(2) C23 H23 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 -176.31(13) O3 S1 C1 C2 56.86(15) C13 S1 C1 C2 -60.41(15) S1 C1 C2 O1 -51.69(18) S1 C1 C2 C3 -174.42(12) S1 C1 C2 C4 68.78(17) C5 N2 C4 O2 -1.2(3) C5 N2 C4 C2 -178.81(15) O1 C2 C4 O2 176.84(15) C3 C2 C4 O2 -63.6(2) C1 C2 C4 O2 54.1(2) O1 C2 C4 N2 -5.4(2) C3 C2 C4 N2 114.11(16) C1 C2 C4 N2 -128.21(15) C4 N2 C5 C6 173.53(17) C4 N2 C5 C10 -7.4(3) C10 C5 C6 C7 0.5(3) N2 C5 C6 C7 179.64(16) C5 C6 C7 C8 -0.7(3) C6 C7 C8 C9 0.0(3) C6 C7 C8 C11 -179.78(17) C7 C8 C9 C10 0.8(3) C11 C8 C9 C10 -179.40(16) C7 C8 C9 C12 -179.69(16) C11 C8 C9 C12 0.1(3) C8 C9 C10 C5 -1.0(3) C12 C9 C10 C5 179.54(16) C6 C5 C10 C9 0.3(3) N2 C5 C10 C9 -178.77(16) C10 C9 C12 F3 0.2(2) C8 C9 C12 F3 -179.31(16) C10 C9 C12 F1 -120.93(18) C8 C9 C12 F1 59.6(2) C10 C9 C12 F2 119.91(17) C8 C9 C12 F2 -59.6(2) O4 S1 C13 C18 -141.08(14) O3 S1 C13 C18 -13.64(16) C1 S1 C13 C18 105.24(15) O4 S1 C13 C14 39.19(16) O3 S1 C13 C14 166.62(14) C1 S1 C13 C14 -74.50(15) C18 C13 C14 C15 -1.4(3) S1 C13 C14 C15 178.30(14) C13 C14 C15 C16 0.6(3) C14 C15 C16 F4 -178.34(16) C14 C15 C16 C17 0.8(3) F4 C16 C17 C18 177.78(16) C15 C16 C17 C18 -1.3(3) C16 C17 C18 C13 0.5(3) C14 C13 C18 C17 0.9(3) S1 C13 C18 C17 -178.86(13) C24 C19 C20 C21 1.2(3) C25 C19 C20 C21 -178.82(17) C19 C20 C21 C22 1.0(3) C20 C21 C22 C23 -1.2(3) C21 C22 C23 C24 -0.9(3) C22 C23 C24 O6 -176.87(16) C22 C23 C24 C19 3.2(3) C20 C19 C24 O6 176.77(16) C25 C19 C24 O6 -3.2(3) C20 C19 C24 C23 -3.3(3) C25 C19 C24 C23 176.71(16) C20 C19 C25 O5 -165.50(16) C24 C19 C25 O5 14.5(2) C20 C19 C25 N3 14.8(3) C24 C19 C25 N3 -165.22(17)