#------------------------------------------------------------------------------ #$Date: 2020-05-14 06:05:36 +0300 (Thu, 14 May 2020) $ #$Revision: 252046 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240513.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_7240513 loop_ _publ_author_name 'Chang, Meng-Yang' 'Lai, Kai-Xiang' 'Chang, Yu-Lun' _publ_section_title ; In(OTf)3-catalyzed intramolecular hydroarylation of \a-phenylallyl \b-ketosulfones -- synthesis of sulfonyl 1-benzosuberones and 1-tetralones ; _journal_issue 31 _journal_name_full 'RSC Advances' _journal_page_first 18231 _journal_paper_doi 10.1039/D0RA01962C _journal_volume 10 _journal_year 2020 _chemical_formula_sum 'C26 H26 O5 S' _chemical_formula_weight 450.53 _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-2014/6 _audit_update_record ; 2019-05-13 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 114.461(2) _cell_angle_beta 90.355(3) _cell_angle_gamma 96.581(3) _cell_formula_units_Z 2 _cell_length_a 8.6479(4) _cell_length_b 11.7181(6) _cell_length_c 12.4402(7) _cell_measurement_reflns_used 6947 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.5661 _cell_measurement_theta_min 2.3749 _cell_volume 1137.93(10) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.993 _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 0.0331 _diffrn_reflns_av_unetI/netI 0.0295 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 28716 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.452 _diffrn_reflns_theta_min 1.802 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.7128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/4 (Bruker AXS Inc.)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description lump _exptl_crystal_F_000 476 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.223 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 292 _refine_ls_number_reflns 4674 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0434 _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^)+(0.0457P)^2^+0.4510P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1020 _refine_ls_wR_factor_ref 0.1136 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3473 _reflns_number_total 4674 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra01962c2.cif _cod_data_source_block mo_190226_0m _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 7240513 _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. ; _shelxl_version_number 2014/6 _shelx_res_file ; TITL mo_190226_0m in P-1 CELL 0.71073 8.6479 11.7181 12.4402 114.461 90.355 96.581 ZERR 2.00 0.0004 0.0006 0.0007 0.002 0.003 0.003 LATT 1 SFAC C H O S UNIT 52 52 10 2 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 TEMP 23.000 WGHT 0.045700 0.451000 FVAR 0.83853 S1 4 0.383182 0.069110 0.797222 11.00000 0.03212 0.03527 = 0.04622 0.01275 -0.00131 0.00010 O1 3 1.168909 0.506525 0.802338 11.00000 0.03917 0.05862 = 0.08418 0.04499 0.01171 -0.00047 O2 3 0.307257 0.071195 0.899757 11.00000 0.03968 0.05506 = 0.05002 0.01049 0.01160 -0.00343 O3 3 0.526240 0.326012 0.950501 11.00000 0.04352 0.04212 = 0.07256 0.01057 0.01631 0.00114 O4 3 0.918765 0.617618 0.847271 11.00000 0.05082 0.03925 = 0.07025 0.02814 0.01018 0.00320 O5 3 0.331004 0.139253 0.736432 11.00000 0.04897 0.04482 = 0.07300 0.02464 -0.01353 0.00416 C1 1 0.334313 -0.338774 0.528755 11.00000 0.10242 0.04485 = 0.06667 0.00879 -0.01710 0.00321 C2 1 0.313307 -0.309391 0.646346 11.00000 0.10466 0.04348 = 0.07467 0.02823 -0.01662 -0.00953 AFIX 43 H24 2 0.285725 -0.374009 0.670269 11.00000 -1.20000 AFIX 0 C3 1 0.332590 -0.185264 0.729441 11.00000 0.08159 0.04627 = 0.04630 0.02207 -0.00312 -0.00439 AFIX 43 H3 2 0.318316 -0.166629 0.808719 11.00000 -1.20000 AFIX 0 C4 1 0.372766 -0.089902 0.694605 11.00000 0.03887 0.03744 = 0.04055 0.01479 -0.00156 -0.00162 C5 1 0.587732 0.118471 0.832602 11.00000 0.03062 0.03728 = 0.04070 0.01725 0.00148 -0.00087 AFIX 13 H21 2 0.639229 0.089941 0.757661 11.00000 -1.20000 AFIX 0 C6 1 0.621043 0.261916 0.891141 11.00000 0.03334 0.03858 = 0.04381 0.01449 0.00127 0.00099 C7 1 0.772516 0.318836 0.868173 11.00000 0.03435 0.03483 = 0.03751 0.01199 -0.00045 -0.00308 C8 1 0.774991 0.439987 0.871025 11.00000 0.03570 0.03589 = 0.04772 0.01475 0.00163 0.00136 AFIX 43 H19 2 0.685416 0.479677 0.888915 11.00000 -1.20000 AFIX 0 C9 1 0.906711 0.501056 0.847987 11.00000 0.04214 0.03550 = 0.04200 0.01676 0.00100 -0.00114 C10 1 1.042103 0.440396 0.823241 11.00000 0.03540 0.04553 = 0.04368 0.02146 0.00242 -0.00286 C11 1 1.312993 0.456386 0.793725 11.00000 0.03822 0.06812 = 0.08196 0.04207 0.00925 -0.00167 AFIX 137 H15 2 1.334478 0.443989 0.863669 11.00000 -1.50000 H2 2 1.395230 0.514441 0.786032 11.00000 -1.50000 H14 2 1.306435 0.376917 0.725667 11.00000 -1.50000 AFIX 0 C12 1 0.907028 0.258504 0.845688 11.00000 0.03274 0.03691 = 0.03776 0.01608 -0.00038 -0.00178 C13 1 0.926169 0.135294 0.855498 11.00000 0.03016 0.04270 = 0.04112 0.02115 -0.00412 -0.00087 AFIX 13 H13 2 1.034037 0.146308 0.886264 11.00000 -1.20000 AFIX 0 C14 1 0.825152 0.114311 0.948711 11.00000 0.03955 0.05308 = 0.04274 0.02730 -0.00412 -0.00161 AFIX 23 H6 2 0.872890 0.058814 0.975310 11.00000 -1.20000 H7 2 0.825397 0.194835 1.016396 11.00000 -1.20000 AFIX 0 C15 1 0.656518 0.057763 0.906323 11.00000 0.03956 0.05339 = 0.05016 0.03208 -0.00067 -0.00326 AFIX 23 H4 2 0.594730 0.070321 0.974200 11.00000 -1.20000 H5 2 0.651999 -0.032501 0.859145 11.00000 -1.20000 AFIX 0 C16 1 0.912586 0.017158 0.738814 11.00000 0.03132 0.04359 = 0.04623 0.02128 0.00052 -0.00106 C17 1 0.949486 -0.094929 0.739335 11.00000 0.06219 0.04266 = 0.06131 0.02291 -0.01002 -0.00350 AFIX 43 H12 2 0.983082 -0.095361 0.810310 11.00000 -1.20000 AFIX 0 C18 1 0.937805 -0.204839 0.638299 11.00000 0.07965 0.04229 = 0.08718 0.01602 -0.01127 -0.00208 AFIX 43 H11 2 0.963193 -0.278489 0.641345 11.00000 -1.20000 AFIX 0 C19 1 0.888988 -0.206266 0.533324 11.00000 0.07822 0.05750 = 0.06626 0.00379 -0.00054 0.00310 AFIX 43 H10 2 0.879642 -0.281057 0.464849 11.00000 -1.20000 AFIX 0 C20 1 0.853555 -0.096599 0.529004 11.00000 0.07072 0.08261 = 0.04225 0.01734 0.00351 0.00790 AFIX 43 H9 2 0.821110 -0.097060 0.457395 11.00000 -1.20000 AFIX 0 C21 1 0.866250 0.014622 0.631490 11.00000 0.05216 0.05980 = 0.04669 0.02439 0.00620 0.01092 AFIX 43 H8 2 0.843176 0.088528 0.627747 11.00000 -1.20000 AFIX 0 C22 1 1.040305 0.322682 0.823394 11.00000 0.03294 0.04469 = 0.04744 0.02309 0.00337 0.00396 AFIX 43 H20 2 1.131202 0.284628 0.808085 11.00000 -1.20000 AFIX 0 C23 1 0.788945 0.685946 0.884858 11.00000 0.06364 0.03851 = 0.06917 0.02008 0.00951 0.00942 AFIX 137 H16 2 0.702488 0.644923 0.827864 11.00000 -1.50000 H18 2 0.816230 0.770600 0.891889 11.00000 -1.50000 H17 2 0.760488 0.688437 0.960195 11.00000 -1.50000 AFIX 0 C24 1 0.393530 -0.118283 0.577382 11.00000 0.10673 0.04898 = 0.04804 0.02021 0.01091 -0.00530 AFIX 43 H22 2 0.420020 -0.053886 0.552987 11.00000 -1.20000 AFIX 0 C25 1 0.375021 -0.241849 0.496679 11.00000 0.14533 0.06343 = 0.04466 0.01091 0.00986 0.00596 AFIX 43 H23 2 0.390667 -0.260279 0.417610 11.00000 -1.20000 AFIX 0 C26 1 0.307072 -0.475192 0.437513 11.00000 0.20224 0.05312 = 0.09813 -0.00678 -0.03067 -0.00051 AFIX 137 H26A 2 0.199879 -0.496296 0.408267 11.00000 -1.50000 H26B 2 0.331157 -0.529919 0.473461 11.00000 -1.50000 H26C 2 0.372962 -0.485584 0.373140 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM mo_190226_0m in P-1 REM R1 = 0.0434 for 3473 Fo > 4sig(Fo) and 0.0662 for all 4674 data REM 292 parameters refined using 0 restraints END WGHT 0.0457 0.4511 REM Highest difference peak 0.223, deepest hole -0.289, 1-sigma level 0.038 Q1 1 0.2984 0.1251 0.8585 11.00000 0.05 0.22 Q2 1 0.2373 -0.3247 0.5589 11.00000 0.05 0.22 Q3 1 0.3854 -0.0236 0.7443 11.00000 0.05 0.21 Q4 1 0.9086 0.0721 0.8011 11.00000 0.05 0.18 Q5 1 0.4960 0.0945 0.8237 11.00000 0.05 0.18 ; _shelx_res_checksum 3734 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 0.38318(5) 0.06911(5) 0.79722(5) 0.03968(15) Uani 1 1 d . . . . . O1 O 1.16891(16) 0.50653(14) 0.80234(15) 0.0561(4) Uani 1 1 d . . . . . O2 O 0.30726(16) 0.07119(14) 0.89976(13) 0.0529(4) Uani 1 1 d . . . . . O3 O 0.52624(17) 0.32601(14) 0.95050(14) 0.0575(4) Uani 1 1 d . . . . . O4 O 0.91876(17) 0.61762(13) 0.84727(14) 0.0519(4) Uani 1 1 d . . . . . O5 O 0.33100(17) 0.13925(14) 0.73643(14) 0.0558(4) Uani 1 1 d . . . . . C1 C 0.3343(4) -0.3388(2) 0.5288(3) 0.0768(8) Uani 1 1 d . . . . . C2 C 0.3133(4) -0.3094(2) 0.6463(3) 0.0748(8) Uani 1 1 d . . . . . H24 H 0.2857 -0.3740 0.6703 0.090 Uiso 1 1 calc R U . . . C3 C 0.3326(3) -0.1853(2) 0.7294(2) 0.0582(6) Uani 1 1 d . . . . . H3 H 0.3183 -0.1666 0.8087 0.070 Uiso 1 1 calc R U . . . C4 C 0.3728(2) -0.08990(18) 0.69460(17) 0.0400(4) Uani 1 1 d . . . . . C5 C 0.5877(2) 0.11847(17) 0.83260(17) 0.0363(4) Uani 1 1 d . . . . . H21 H 0.6392 0.0899 0.7577 0.044 Uiso 1 1 calc R U . . . C6 C 0.6210(2) 0.26192(18) 0.89114(18) 0.0398(4) Uani 1 1 d . . . . . C7 C 0.7725(2) 0.31884(18) 0.86817(16) 0.0373(4) Uani 1 1 d . . . . . C8 C 0.7750(2) 0.43999(18) 0.87102(17) 0.0410(5) Uani 1 1 d . . . . . H19 H 0.6854 0.4797 0.8889 0.049 Uiso 1 1 calc R U . . . C9 C 0.9067(2) 0.50106(18) 0.84799(17) 0.0402(5) Uani 1 1 d . . . . . C10 C 1.0421(2) 0.44040(19) 0.82324(18) 0.0413(5) Uani 1 1 d . . . . . C11 C 1.3130(2) 0.4564(2) 0.7937(2) 0.0599(6) Uani 1 1 d . . . . . H15 H 1.3345 0.4440 0.8637 0.090 Uiso 1 1 calc R U . . . H2 H 1.3952 0.5144 0.7860 0.090 Uiso 1 1 calc R U . . . H14 H 1.3064 0.3769 0.7257 0.090 Uiso 1 1 calc R U . . . C12 C 0.9070(2) 0.25850(18) 0.84569(16) 0.0362(4) Uani 1 1 d . . . . . C13 C 0.9262(2) 0.13529(18) 0.85550(17) 0.0373(4) Uani 1 1 d . . . . . H13 H 1.0340 0.1463 0.8863 0.045 Uiso 1 1 calc R U . . . C14 C 0.8252(2) 0.1143(2) 0.94871(18) 0.0433(5) Uani 1 1 d . . . . . H6 H 0.8729 0.0588 0.9753 0.052 Uiso 1 1 calc R U . . . H7 H 0.8254 0.1948 1.0164 0.052 Uiso 1 1 calc R U . . . C15 C 0.6565(2) 0.0578(2) 0.90632(19) 0.0450(5) Uani 1 1 d . . . . . H4 H 0.5947 0.0703 0.9742 0.054 Uiso 1 1 calc R U . . . H5 H 0.6520 -0.0325 0.8591 0.054 Uiso 1 1 calc R U . . . C16 C 0.9126(2) 0.01716(19) 0.73881(18) 0.0400(5) Uani 1 1 d . . . . . C17 C 0.9495(3) -0.0949(2) 0.7393(2) 0.0559(6) Uani 1 1 d . . . . . H12 H 0.9831 -0.0954 0.8103 0.067 Uiso 1 1 calc R U . . . C18 C 0.9378(3) -0.2048(2) 0.6383(3) 0.0743(8) Uani 1 1 d . . . . . H11 H 0.9632 -0.2785 0.6413 0.089 Uiso 1 1 calc R U . . . C19 C 0.8890(3) -0.2063(3) 0.5333(3) 0.0752(8) Uani 1 1 d . . . . . H10 H 0.8796 -0.2811 0.4648 0.090 Uiso 1 1 calc R U . . . C20 C 0.8536(3) -0.0966(3) 0.5290(2) 0.0683(7) Uani 1 1 d . . . . . H9 H 0.8211 -0.0971 0.4574 0.082 Uiso 1 1 calc R U . . . C21 C 0.8663(3) 0.0146(2) 0.63149(19) 0.0518(5) Uani 1 1 d . . . . . H8 H 0.8432 0.0885 0.6277 0.062 Uiso 1 1 calc R U . . . C22 C 1.0403(2) 0.32268(19) 0.82339(17) 0.0405(5) Uani 1 1 d . . . . . H20 H 1.1312 0.2846 0.8081 0.049 Uiso 1 1 calc R U . . . C23 C 0.7889(3) 0.6859(2) 0.8849(2) 0.0576(6) Uani 1 1 d . . . . . H16 H 0.7025 0.6449 0.8279 0.086 Uiso 1 1 calc R U . . . H18 H 0.8162 0.7706 0.8919 0.086 Uiso 1 1 calc R U . . . H17 H 0.7605 0.6884 0.9602 0.086 Uiso 1 1 calc R U . . . C24 C 0.3935(3) -0.1183(2) 0.5774(2) 0.0692(7) Uani 1 1 d . . . . . H22 H 0.4200 -0.0539 0.5530 0.083 Uiso 1 1 calc R U . . . C25 C 0.3750(4) -0.2418(3) 0.4967(2) 0.0890(10) Uani 1 1 d . . . . . H23 H 0.3907 -0.2603 0.4176 0.107 Uiso 1 1 calc R U . . . C26 C 0.3071(6) -0.4752(3) 0.4375(3) 0.1324(16) Uani 1 1 d . . . . . H26A H 0.1999 -0.4963 0.4083 0.199 Uiso 1 1 calc R U . . . H26B H 0.3312 -0.5299 0.4735 0.199 Uiso 1 1 calc R U . . . H26C H 0.3730 -0.4856 0.3731 0.199 Uiso 1 1 calc R U . . . 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 0.0321(2) 0.0353(3) 0.0462(3) 0.0127(2) -0.00131(19) 0.00010(19) O1 0.0392(8) 0.0586(10) 0.0842(11) 0.0450(9) 0.0117(7) -0.0005(7) O2 0.0397(8) 0.0551(9) 0.0500(9) 0.0105(7) 0.0116(6) -0.0034(6) O3 0.0435(8) 0.0421(9) 0.0726(11) 0.0106(8) 0.0163(7) 0.0011(7) O4 0.0508(9) 0.0393(8) 0.0702(10) 0.0281(8) 0.0102(7) 0.0032(6) O5 0.0490(9) 0.0448(9) 0.0730(11) 0.0246(8) -0.0135(7) 0.0042(7) C1 0.102(2) 0.0449(15) 0.0667(18) 0.0088(13) -0.0171(15) 0.0032(14) C2 0.105(2) 0.0435(15) 0.0747(19) 0.0282(14) -0.0166(16) -0.0095(14) C3 0.0816(17) 0.0463(14) 0.0463(13) 0.0221(11) -0.0031(11) -0.0044(12) C4 0.0389(10) 0.0374(11) 0.0406(11) 0.0148(9) -0.0016(8) -0.0016(8) C5 0.0306(9) 0.0373(11) 0.0407(11) 0.0172(9) 0.0015(8) -0.0009(7) C6 0.0333(10) 0.0386(11) 0.0438(11) 0.0145(9) 0.0013(8) 0.0010(8) C7 0.0343(10) 0.0348(10) 0.0375(10) 0.0120(8) -0.0004(8) -0.0031(8) C8 0.0357(10) 0.0359(11) 0.0477(12) 0.0147(9) 0.0016(8) 0.0014(8) C9 0.0421(11) 0.0355(11) 0.0420(11) 0.0168(9) 0.0010(8) -0.0011(8) C10 0.0354(10) 0.0455(12) 0.0437(11) 0.0215(10) 0.0024(8) -0.0029(8) C11 0.0382(12) 0.0681(16) 0.0820(17) 0.0421(14) 0.0093(11) -0.0017(10) C12 0.0327(9) 0.0369(11) 0.0378(10) 0.0161(9) -0.0004(8) -0.0018(8) C13 0.0302(9) 0.0427(11) 0.0411(11) 0.0212(9) -0.0041(8) -0.0009(8) C14 0.0396(10) 0.0531(13) 0.0427(11) 0.0273(10) -0.0041(8) -0.0016(9) C15 0.0396(11) 0.0534(13) 0.0502(12) 0.0321(11) -0.0007(9) -0.0033(9) C16 0.0313(9) 0.0436(12) 0.0462(12) 0.0213(10) 0.0005(8) -0.0011(8) C17 0.0622(14) 0.0427(13) 0.0613(15) 0.0229(12) -0.0100(11) -0.0035(10) C18 0.0796(18) 0.0423(15) 0.087(2) 0.0160(14) -0.0113(15) -0.0021(12) C19 0.0782(18) 0.0575(17) 0.0663(18) 0.0038(14) -0.0005(14) 0.0031(14) C20 0.0707(17) 0.083(2) 0.0423(13) 0.0173(13) 0.0035(11) 0.0079(14) C21 0.0522(13) 0.0598(15) 0.0467(13) 0.0244(11) 0.0062(10) 0.0109(10) C22 0.0329(10) 0.0447(12) 0.0474(12) 0.0231(10) 0.0034(8) 0.0040(8) C23 0.0636(14) 0.0385(12) 0.0692(16) 0.0201(11) 0.0095(12) 0.0094(10) C24 0.107(2) 0.0490(15) 0.0480(14) 0.0202(12) 0.0109(13) -0.0053(14) C25 0.145(3) 0.0634(19) 0.0447(15) 0.0109(14) 0.0099(16) 0.0060(18) C26 0.202(5) 0.0531(19) 0.098(3) -0.0068(18) -0.031(3) -0.001(2) 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' O O 0.0106 0.0060 '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 O5 S1 O2 119.60(10) . . ? O5 S1 C4 107.71(9) . . ? O2 S1 C4 107.61(9) . . ? O5 S1 C5 107.07(9) . . ? O2 S1 C5 109.85(9) . . ? C4 S1 C5 103.88(9) . . ? C10 O1 C11 116.93(16) . . ? C9 O4 C23 116.92(16) . . ? C25 C1 C2 118.0(2) . . ? C25 C1 C26 121.4(3) . . ? C2 C1 C26 120.5(3) . . ? C1 C2 C3 121.0(2) . . ? C1 C2 H24 119.5 . . ? C3 C2 H24 119.5 . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C24 119.7(2) . . ? C3 C4 S1 120.32(16) . . ? C24 C4 S1 119.76(17) . . ? C6 C5 C15 112.16(16) . . ? C6 C5 S1 110.50(13) . . ? C15 C5 S1 112.54(13) . . ? C6 C5 H21 107.1 . . ? C15 C5 H21 107.1 . . ? S1 C5 H21 107.1 . . ? O3 C6 C7 122.09(18) . . ? O3 C6 C5 121.34(17) . . ? C7 C6 C5 116.53(16) . . ? C12 C7 C8 120.66(17) . . ? C12 C7 C6 123.50(17) . . ? C8 C7 C6 115.84(17) . . ? C9 C8 C7 121.36(18) . . ? C9 C8 H19 119.3 . . ? C7 C8 H19 119.3 . . ? O4 C9 C8 125.24(18) . . ? O4 C9 C10 116.27(17) . . ? C8 C9 C10 118.49(18) . . ? O1 C10 C22 124.50(18) . . ? O1 C10 C9 115.52(17) . . ? C22 C10 C9 119.97(17) . . ? O1 C11 H15 109.5 . . ? O1 C11 H2 109.5 . . ? H15 C11 H2 109.5 . . ? O1 C11 H14 109.5 . . ? H15 C11 H14 109.5 . . ? H2 C11 H14 109.5 . . ? C22 C12 C7 117.08(17) . . ? C22 C12 C13 116.70(16) . . ? C7 C12 C13 125.92(16) . . ? C12 C13 C16 115.76(15) . . ? C12 C13 C14 113.00(16) . . ? C16 C13 C14 111.78(16) . . ? C12 C13 H13 105.0 . . ? C16 C13 H13 105.0 . . ? C14 C13 H13 105.0 . . ? C15 C14 C13 114.97(16) . . ? C15 C14 H6 108.5 . . ? C13 C14 H6 108.5 . . ? C15 C14 H7 108.5 . . ? C13 C14 H7 108.5 . . ? H6 C14 H7 107.5 . . ? C14 C15 C5 111.34(16) . . ? C14 C15 H4 109.4 . . ? C5 C15 H4 109.4 . . ? C14 C15 H5 109.4 . . ? C5 C15 H5 109.4 . . ? H4 C15 H5 108.0 . . ? C21 C16 C17 117.3(2) . . ? C21 C16 C13 123.88(19) . . ? C17 C16 C13 118.77(18) . . ? C18 C17 C16 121.9(2) . . ? C18 C17 H12 119.1 . . ? C16 C17 H12 119.1 . . ? C19 C18 C17 120.0(3) . . ? C19 C18 H11 120.0 . . ? C17 C18 H11 120.0 . . ? C18 C19 C20 119.8(3) . . ? C18 C19 H10 120.1 . . ? C20 C19 H10 120.1 . . ? C19 C20 C21 120.0(2) . . ? C19 C20 H9 120.0 . . ? C21 C20 H9 120.0 . . ? C16 C21 C20 121.0(2) . . ? C16 C21 H8 119.5 . . ? C20 C21 H8 119.5 . . ? C10 C22 C12 122.41(18) . . ? C10 C22 H20 118.8 . . ? C12 C22 H20 118.8 . . ? O4 C23 H16 109.5 . . ? O4 C23 H18 109.5 . . ? H16 C23 H18 109.5 . . ? O4 C23 H17 109.5 . . ? H16 C23 H17 109.5 . . ? H18 C23 H17 109.5 . . ? C25 C24 C4 119.6(2) . . ? C25 C24 H22 120.2 . . ? C4 C24 H22 120.2 . . ? C1 C25 C24 121.9(3) . . ? C1 C25 H23 119.0 . . ? C24 C25 H23 119.0 . . ? C1 C26 H26A 109.5 . . ? C1 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C1 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 O5 1.4306(15) . ? S1 O2 1.4307(15) . ? S1 C4 1.761(2) . ? S1 C5 1.7895(18) . ? O1 C10 1.359(2) . ? O1 C11 1.424(3) . ? O3 C6 1.213(2) . ? O4 C9 1.362(2) . ? O4 C23 1.422(3) . ? C1 C25 1.363(4) . ? C1 C2 1.376(4) . ? C1 C26 1.519(4) . ? C2 C3 1.382(3) . ? C2 H24 0.9300 . ? C3 C4 1.368(3) . ? C3 H3 0.9300 . ? C4 C24 1.373(3) . ? C5 C6 1.520(3) . ? C5 C15 1.527(3) . ? C5 H21 0.9800 . ? C6 C7 1.485(3) . ? C7 C12 1.400(3) . ? C7 C8 1.403(3) . ? C8 C9 1.371(3) . ? C8 H19 0.9300 . ? C9 C10 1.409(3) . ? C10 C22 1.378(3) . ? C11 H15 0.9600 . ? C11 H2 0.9600 . ? C11 H14 0.9600 . ? C12 C22 1.396(3) . ? C12 C13 1.526(3) . ? C13 C16 1.528(3) . ? C13 C14 1.539(3) . ? C13 H13 0.9800 . ? C14 C15 1.524(3) . ? C14 H6 0.9700 . ? C14 H7 0.9700 . ? C15 H4 0.9700 . ? C15 H5 0.9700 . ? C16 C21 1.379(3) . ? C16 C17 1.389(3) . ? C17 C18 1.370(3) . ? C17 H12 0.9300 . ? C18 C19 1.363(4) . ? C18 H11 0.9300 . ? C19 C20 1.377(4) . ? C19 H10 0.9300 . ? C20 C21 1.388(3) . ? C20 H9 0.9300 . ? C21 H8 0.9300 . ? C22 H20 0.9300 . ? C23 H16 0.9600 . ? C23 H18 0.9600 . ? C23 H17 0.9600 . ? C24 C25 1.368(4) . ? C24 H22 0.9300 . ? C25 H23 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ?