#------------------------------------------------------------------------------ #$Date: 2020-05-14 06:05:36 +0300 (Thu, 14 May 2020) $ #$Revision: 252046 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240515.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_7240515 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 'C25 H24 O5 S' _chemical_formula_weight 436.50 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 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 90 _cell_angle_beta 107.381(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.2830(19) _cell_length_b 19.038(4) _cell_length_c 9.2274(14) _cell_measurement_reflns_used 3328 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.1380 _cell_measurement_theta_min 2.6669 _cell_volume 2059.2(6) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.994 _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 0.0578 _diffrn_reflns_av_unetI/netI 0.0641 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 14957 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.458 _diffrn_reflns_theta_min 1.737 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/4 (Bruker AXS Inc.)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description lump _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.441 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 4226 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0471 _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^)+(0.0492P)^2^+0.4223P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1017 _refine_ls_wR_factor_ref 0.1146 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3042 _reflns_number_total 4226 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra01962c2.cif _cod_data_source_block 181151LT _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_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240515 _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 181151LT in P2(1)/c CELL 0.71073 12.2830 19.0375 9.2274 90.000 107.381 90.000 ZERR 4.00 0.0019 0.0038 0.0014 0.000 0.009 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H O S UNIT 100 96 20 4 TEMP -173.000 ACTA L.S. 4 FMAP 2 PLAN 5 BOND $H WGHT 0.049200 0.422300 FVAR 0.12154 S1 4 0.371001 0.130469 0.448626 11.00000 0.01372 0.02129 = 0.01726 -0.00177 0.00464 -0.00084 O1 3 0.270348 0.167150 0.136075 11.00000 0.02297 0.03490 = 0.01901 -0.00097 0.00784 -0.00679 O2 3 -0.206717 0.054293 -0.246895 11.00000 0.01621 0.03630 = 0.02070 -0.00821 0.00031 -0.00137 O3 3 -0.010565 0.045719 -0.303378 11.00000 0.01971 0.03488 = 0.01587 -0.00623 0.00285 0.00112 O4 3 0.414007 0.073187 0.380731 11.00000 0.02201 0.02626 = 0.02411 -0.00521 0.00999 0.00309 O5 3 0.422311 0.198507 0.454562 11.00000 0.01876 0.02418 = 0.02217 0.00008 0.00612 -0.00557 C1 1 0.394229 0.069083 0.929082 11.00000 0.01905 0.03387 = 0.01976 0.00630 0.00218 0.00115 AFIX 43 H1 2 0.398956 0.056138 1.030210 11.00000 -1.20000 AFIX 0 C2 1 0.395845 0.139417 0.891878 11.00000 0.01843 0.02725 = 0.01959 -0.00235 0.00439 -0.00234 AFIX 43 H22 2 0.402578 0.174345 0.967585 11.00000 -1.20000 AFIX 0 C3 1 0.387677 0.158908 0.744726 11.00000 0.01712 0.01781 = 0.02165 -0.00177 0.00515 -0.00132 AFIX 43 H23 2 0.388059 0.207059 0.717849 11.00000 -1.20000 AFIX 0 C4 1 0.378872 0.106396 0.636680 11.00000 0.00999 0.02217 = 0.01936 -0.00013 0.00164 0.00015 C5 1 0.218560 0.137559 0.357532 11.00000 0.01306 0.02164 = 0.01632 -0.00160 0.00422 -0.00289 AFIX 13 H4 2 0.181452 0.093448 0.377995 11.00000 -1.20000 AFIX 0 C6 1 0.167094 0.199508 0.419179 11.00000 0.01975 0.02883 = 0.01988 -0.00515 0.00566 -0.00032 AFIX 23 H5 2 0.216100 0.241295 0.424440 11.00000 -1.20000 H6 2 0.166226 0.188505 0.523688 11.00000 -1.20000 AFIX 0 C7 1 0.045390 0.217019 0.321568 11.00000 0.02359 0.02310 = 0.02265 -0.00199 0.00720 0.00299 AFIX 23 H7 2 0.049347 0.243426 0.230851 11.00000 -1.20000 H8 2 0.009651 0.248056 0.380497 11.00000 -1.20000 AFIX 0 C8 1 -0.030893 0.152406 0.269394 11.00000 0.01686 0.02485 = 0.01565 0.00017 0.00376 0.00204 AFIX 13 H13 2 -0.001869 0.115255 0.348095 11.00000 -1.20000 AFIX 0 C9 1 -0.152910 0.168119 0.266542 11.00000 0.01691 0.02540 = 0.01302 -0.00236 0.00443 0.00195 C10 1 -0.198822 0.136621 0.370999 11.00000 0.02401 0.02030 = 0.01850 -0.00103 0.00547 0.00136 AFIX 43 H9 2 -0.153521 0.105028 0.444140 11.00000 -1.20000 AFIX 0 C11 1 -0.309714 0.150647 0.369963 11.00000 0.02789 0.02519 = 0.02374 -0.00427 0.01574 -0.00582 AFIX 43 H12 2 -0.339385 0.128999 0.442923 11.00000 -1.20000 AFIX 0 C12 1 -0.377525 0.195887 0.263621 11.00000 0.01811 0.02967 = 0.02501 -0.00408 0.00762 0.00462 AFIX 43 H2 2 -0.454263 0.204437 0.261125 11.00000 -1.20000 AFIX 0 C13 1 0.385856 0.017600 0.821400 11.00000 0.02141 0.02569 = 0.02472 0.00771 0.00271 0.00202 AFIX 43 H3 2 0.385150 -0.030512 0.848434 11.00000 -1.20000 AFIX 0 C14 1 0.378452 0.036185 0.673265 11.00000 0.01738 0.02180 = 0.02387 -0.00280 0.00253 0.00091 AFIX 43 H24 2 0.373179 0.001087 0.598290 11.00000 -1.20000 AFIX 0 C15 1 0.196583 0.144236 0.186794 11.00000 0.01809 0.01915 = 0.01803 -0.00143 0.00694 0.00144 C16 1 0.084039 0.120453 0.085389 11.00000 0.01740 0.02131 = 0.01381 0.00271 0.00174 0.00018 C17 1 -0.019783 0.122920 0.119389 11.00000 0.01787 0.01888 = 0.01588 0.00231 0.00239 0.00167 C18 1 -0.332008 0.228582 0.160742 11.00000 0.02086 0.03208 = 0.02250 0.00513 0.00408 0.00907 AFIX 43 H11 2 -0.377374 0.260433 0.088297 11.00000 -1.20000 AFIX 0 C19 1 -0.220658 0.215099 0.162874 11.00000 0.02449 0.03272 = 0.02161 0.00603 0.01042 0.00297 AFIX 43 H10 2 -0.190197 0.238303 0.092462 11.00000 -1.20000 AFIX 0 C20 1 -0.116924 0.099909 0.006228 11.00000 0.01509 0.02483 = 0.02053 0.00252 0.00494 0.00157 AFIX 43 H21 2 -0.188380 0.101019 0.026333 11.00000 -1.20000 AFIX 0 C21 1 -0.113305 0.075700 -0.133190 11.00000 0.01530 0.02102 = 0.01468 0.00011 -0.00046 -0.00103 C22 1 -0.316070 0.069815 -0.229300 11.00000 0.01716 0.03406 = 0.02983 -0.00613 0.00328 -0.00280 AFIX 137 H16 2 -0.326126 0.043038 -0.143495 11.00000 -1.50000 H15 2 -0.375955 0.056865 -0.322238 11.00000 -1.50000 H14 2 -0.321012 0.120169 -0.210117 11.00000 -1.50000 AFIX 0 C23 1 -0.008433 0.071758 -0.164309 11.00000 0.02136 0.02174 = 0.01495 -0.00048 0.00461 0.00385 C24 1 0.098411 0.040229 -0.328933 11.00000 0.02188 0.03634 = 0.01900 -0.00821 0.00656 0.00069 AFIX 137 H17 2 0.134449 0.086648 -0.318025 11.00000 -1.50000 H19 2 0.088538 0.022395 -0.431695 11.00000 -1.50000 H18 2 0.146895 0.007883 -0.254585 11.00000 -1.50000 AFIX 0 C25 1 0.088101 0.095107 -0.055909 11.00000 0.01766 0.02248 = 0.01842 0.00096 0.00602 0.00205 AFIX 43 H20 2 0.159145 0.094055 -0.077151 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 181151LT in P2(1)/c REM R1 = 0.0471 for 3042 Fo > 4sig(Fo) and 0.0745 for all 4226 data REM 282 parameters refined using 0 restraints END WGHT 0.0492 0.4222 REM Highest difference peak 0.441, deepest hole -0.461, 1-sigma level 0.061 Q1 1 0.3762 0.1228 0.5595 11.00000 0.05 0.44 Q2 1 -0.1009 0.0339 -0.3395 11.00000 0.05 0.32 Q3 1 0.2853 0.1321 0.3884 11.00000 0.05 0.32 Q4 1 0.0352 0.1179 0.4175 11.00000 0.05 0.30 Q5 1 -0.0667 0.0941 -0.1605 11.00000 0.05 0.27 ; _shelx_res_checksum 21061 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 S1 S 0.37100(4) 0.13047(3) 0.44863(6) 0.01742(16) Uani 1 1 d . . . . . O1 O 0.27035(13) 0.16715(10) 0.13608(17) 0.0253(4) Uani 1 1 d . . . . . O2 O -0.20672(12) 0.05429(10) -0.24690(17) 0.0255(4) Uani 1 1 d . . . . . O3 O -0.01057(12) 0.04572(9) -0.30338(17) 0.0240(4) Uani 1 1 d . . . . . O4 O 0.41401(12) 0.07319(9) 0.38073(17) 0.0234(4) Uani 1 1 d . . . . . O5 O 0.42231(12) 0.19851(9) 0.45456(17) 0.0217(4) Uani 1 1 d . . . . . C1 C 0.39423(18) 0.06908(15) 0.9291(3) 0.0250(6) Uani 1 1 d . . . . . H1 H 0.3990 0.0561 1.0302 0.030 Uiso 1 1 calc R U . . . C2 C 0.39585(18) 0.13942(14) 0.8919(3) 0.0220(5) Uani 1 1 d . . . . . H22 H 0.4026 0.1743 0.9676 0.026 Uiso 1 1 calc R U . . . C3 C 0.38768(17) 0.15891(13) 0.7447(3) 0.0190(5) Uani 1 1 d . . . . . H23 H 0.3881 0.2071 0.7178 0.023 Uiso 1 1 calc R U . . . C4 C 0.37887(16) 0.10640(13) 0.6367(2) 0.0178(5) Uani 1 1 d . . . . . C5 C 0.21856(17) 0.13756(13) 0.3575(2) 0.0170(5) Uani 1 1 d . . . . . H4 H 0.1815 0.0934 0.3780 0.020 Uiso 1 1 calc R U . . . C6 C 0.16709(18) 0.19951(14) 0.4192(3) 0.0229(6) Uani 1 1 d . . . . . H5 H 0.2161 0.2413 0.4244 0.027 Uiso 1 1 calc R U . . . H6 H 0.1662 0.1885 0.5237 0.027 Uiso 1 1 calc R U . . . C7 C 0.04539(18) 0.21702(13) 0.3216(3) 0.0230(5) Uani 1 1 d . . . . . H7 H 0.0493 0.2434 0.2309 0.028 Uiso 1 1 calc R U . . . H8 H 0.0097 0.2481 0.3805 0.028 Uiso 1 1 calc R U . . . C8 C -0.03089(17) 0.15241(13) 0.2694(2) 0.0194(5) Uani 1 1 d . . . . . H13 H -0.0019 0.1153 0.3481 0.023 Uiso 1 1 calc R U . . . C9 C -0.15291(17) 0.16812(13) 0.2665(2) 0.0184(5) Uani 1 1 d . . . . . C10 C -0.19882(18) 0.13662(13) 0.3710(3) 0.0211(5) Uani 1 1 d . . . . . H9 H -0.1535 0.1050 0.4441 0.025 Uiso 1 1 calc R U . . . C11 C -0.30971(19) 0.15065(14) 0.3700(3) 0.0239(6) Uani 1 1 d . . . . . H12 H -0.3394 0.1290 0.4429 0.029 Uiso 1 1 calc R U . . . C12 C -0.37752(19) 0.19589(14) 0.2636(3) 0.0240(6) Uani 1 1 d . . . . . H2 H -0.4543 0.2044 0.2611 0.029 Uiso 1 1 calc R U . . . C13 C 0.38586(18) 0.01760(15) 0.8214(3) 0.0249(6) Uani 1 1 d . . . . . H3 H 0.3851 -0.0305 0.8484 0.030 Uiso 1 1 calc R U . . . C14 C 0.37845(17) 0.03618(13) 0.6733(3) 0.0218(5) Uani 1 1 d . . . . . H24 H 0.3732 0.0011 0.5983 0.026 Uiso 1 1 calc R U . . . C15 C 0.19658(18) 0.14424(13) 0.1868(2) 0.0181(5) Uani 1 1 d . . . . . C16 C 0.08404(17) 0.12045(13) 0.0854(2) 0.0181(5) Uani 1 1 d . . . . . C17 C -0.01978(17) 0.12292(13) 0.1194(2) 0.0181(5) Uani 1 1 d . . . . . C18 C -0.33201(19) 0.22858(14) 0.1607(3) 0.0257(6) Uani 1 1 d . . . . . H11 H -0.3774 0.2604 0.0883 0.031 Uiso 1 1 calc R U . . . C19 C -0.22066(19) 0.21510(14) 0.1629(3) 0.0255(6) Uani 1 1 d . . . . . H10 H -0.1902 0.2383 0.0925 0.031 Uiso 1 1 calc R U . . . C20 C -0.11692(18) 0.09991(13) 0.0062(2) 0.0202(5) Uani 1 1 d . . . . . H21 H -0.1884 0.1010 0.0263 0.024 Uiso 1 1 calc R U . . . C21 C -0.11331(17) 0.07570(13) -0.1332(2) 0.0181(5) Uani 1 1 d . . . . . C22 C -0.31607(18) 0.06981(15) -0.2293(3) 0.0278(6) Uani 1 1 d . . . . . H16 H -0.3261 0.0430 -0.1435 0.042 Uiso 1 1 calc R U . . . H15 H -0.3760 0.0569 -0.3222 0.042 Uiso 1 1 calc R U . . . H14 H -0.3210 0.1202 -0.2101 0.042 Uiso 1 1 calc R U . . . C23 C -0.00843(18) 0.07176(13) -0.1643(2) 0.0195(5) Uani 1 1 d . . . . . C24 C 0.09841(18) 0.04023(15) -0.3289(3) 0.0256(6) Uani 1 1 d . . . . . H17 H 0.1344 0.0866 -0.3180 0.038 Uiso 1 1 calc R U . . . H19 H 0.0885 0.0224 -0.4317 0.038 Uiso 1 1 calc R U . . . H18 H 0.1469 0.0079 -0.2546 0.038 Uiso 1 1 calc R U . . . C25 C 0.08810(18) 0.09511(13) -0.0559(2) 0.0194(5) Uani 1 1 d . . . . . H20 H 0.1591 0.0941 -0.0772 0.023 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 0.0137(3) 0.0213(3) 0.0173(3) -0.0018(2) 0.0046(2) -0.0008(2) O1 0.0230(8) 0.0349(12) 0.0190(8) -0.0010(8) 0.0078(7) -0.0068(8) O2 0.0162(8) 0.0363(12) 0.0207(8) -0.0082(8) 0.0003(7) -0.0014(7) O3 0.0197(8) 0.0349(12) 0.0159(8) -0.0062(8) 0.0029(7) 0.0011(7) O4 0.0220(8) 0.0263(11) 0.0241(9) -0.0052(8) 0.0100(7) 0.0031(7) O5 0.0188(8) 0.0242(10) 0.0222(8) 0.0001(7) 0.0061(7) -0.0056(7) C1 0.0191(11) 0.0339(17) 0.0198(12) 0.0063(11) 0.0022(10) 0.0012(10) C2 0.0184(11) 0.0272(16) 0.0196(12) -0.0024(11) 0.0044(10) -0.0023(10) C3 0.0171(11) 0.0178(14) 0.0216(12) -0.0018(10) 0.0052(9) -0.0013(9) C4 0.0100(10) 0.0222(14) 0.0194(11) -0.0001(10) 0.0016(9) 0.0001(9) C5 0.0131(10) 0.0216(14) 0.0163(11) -0.0016(10) 0.0042(9) -0.0029(9) C6 0.0198(11) 0.0288(16) 0.0199(12) -0.0052(11) 0.0057(10) -0.0003(10) C7 0.0236(12) 0.0231(15) 0.0226(12) -0.0020(11) 0.0072(10) 0.0030(10) C8 0.0169(11) 0.0249(15) 0.0156(11) 0.0002(10) 0.0038(9) 0.0020(9) C9 0.0169(11) 0.0254(15) 0.0130(11) -0.0024(10) 0.0044(9) 0.0020(10) C10 0.0240(12) 0.0203(14) 0.0185(12) -0.0010(10) 0.0055(10) 0.0014(10) C11 0.0279(12) 0.0252(16) 0.0237(13) -0.0043(11) 0.0157(11) -0.0058(10) C12 0.0181(11) 0.0297(16) 0.0250(13) -0.0041(12) 0.0076(10) 0.0046(10) C13 0.0214(12) 0.0257(16) 0.0247(13) 0.0077(11) 0.0027(10) 0.0020(10) C14 0.0174(11) 0.0218(15) 0.0239(13) -0.0028(11) 0.0025(10) 0.0009(10) C15 0.0181(11) 0.0192(14) 0.0180(12) -0.0014(10) 0.0069(9) 0.0014(9) C16 0.0174(11) 0.0213(14) 0.0138(11) 0.0027(10) 0.0017(9) 0.0002(9) C17 0.0179(11) 0.0189(14) 0.0159(11) 0.0023(10) 0.0024(9) 0.0017(9) C18 0.0209(12) 0.0321(17) 0.0225(13) 0.0051(11) 0.0041(10) 0.0091(11) C19 0.0245(12) 0.0327(17) 0.0216(12) 0.0060(11) 0.0104(10) 0.0030(11) C20 0.0151(11) 0.0248(15) 0.0205(12) 0.0025(11) 0.0049(9) 0.0016(10) C21 0.0153(10) 0.0210(14) 0.0147(11) 0.0001(10) -0.0005(9) -0.0010(9) C22 0.0172(11) 0.0341(17) 0.0298(14) -0.0061(12) 0.0033(10) -0.0028(11) C23 0.0214(11) 0.0217(15) 0.0149(11) -0.0005(10) 0.0046(9) 0.0038(10) C24 0.0219(12) 0.0363(17) 0.0190(12) -0.0082(11) 0.0066(10) 0.0007(11) C25 0.0177(11) 0.0225(15) 0.0184(12) 0.0010(10) 0.0060(9) 0.0021(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' 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 O4 119.22(9) . . ? O5 S1 C4 107.57(10) . . ? O4 S1 C4 108.18(11) . . ? O5 S1 C5 109.36(10) . . ? O4 S1 C5 108.54(10) . . ? C4 S1 C5 102.72(10) . . ? C21 O2 C22 116.93(18) . . ? C23 O3 C24 115.10(16) . . ? C13 C1 C2 120.9(2) . . ? C13 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C3 C2 C1 120.1(2) . . ? C3 C2 H22 120.0 . . ? C1 C2 H22 120.0 . . ? C2 C3 C4 118.5(2) . . ? C2 C3 H23 120.7 . . ? C4 C3 H23 120.7 . . ? C14 C4 C3 121.7(2) . . ? C14 C4 S1 119.21(18) . . ? C3 C4 S1 119.07(19) . . ? C15 C5 C6 110.86(19) . . ? C15 C5 S1 108.98(14) . . ? C6 C5 S1 111.71(15) . . ? C15 C5 H4 108.4 . . ? C6 C5 H4 108.4 . . ? S1 C5 H4 108.4 . . ? C5 C6 C7 112.87(18) . . ? C5 C6 H5 109.0 . . ? C7 C6 H5 109.0 . . ? C5 C6 H6 109.0 . . ? C7 C6 H6 109.0 . . ? H5 C6 H6 107.8 . . ? C6 C7 C8 114.0(2) . . ? C6 C7 H7 108.8 . . ? C8 C7 H7 108.8 . . ? C6 C7 H8 108.8 . . ? C8 C7 H8 108.8 . . ? H7 C7 H8 107.6 . . ? C9 C8 C7 110.7(2) . . ? C9 C8 C17 114.10(17) . . ? C7 C8 C17 111.42(18) . . ? C9 C8 H13 106.7 . . ? C7 C8 H13 106.7 . . ? C17 C8 H13 106.7 . . ? C10 C9 C19 118.1(2) . . ? C10 C9 C8 120.3(2) . . ? C19 C9 C8 121.5(2) . . ? C11 C10 C9 120.9(2) . . ? C11 C10 H9 119.5 . . ? C9 C10 H9 119.5 . . ? C12 C11 C10 120.5(2) . . ? C12 C11 H12 119.7 . . ? C10 C11 H12 119.7 . . ? C11 C12 C18 119.1(2) . . ? C11 C12 H2 120.5 . . ? C18 C12 H2 120.5 . . ? C1 C13 C14 119.8(2) . . ? C1 C13 H3 120.1 . . ? C14 C13 H3 120.1 . . ? C4 C14 C13 119.0(2) . . ? C4 C14 H24 120.5 . . ? C13 C14 H24 120.5 . . ? O1 C15 C16 121.65(19) . . ? O1 C15 C5 120.35(19) . . ? C16 C15 C5 117.98(18) . . ? C17 C16 C25 120.39(19) . . ? C17 C16 C15 125.8(2) . . ? C25 C16 C15 113.81(18) . . ? C20 C17 C16 116.9(2) . . ? C20 C17 C8 120.04(18) . . ? C16 C17 C8 123.03(19) . . ? C12 C18 C19 120.4(2) . . ? C12 C18 H11 119.8 . . ? C19 C18 H11 119.8 . . ? C18 C19 C9 121.0(2) . . ? C18 C19 H10 119.5 . . ? C9 C19 H10 119.5 . . ? C21 C20 C17 122.8(2) . . ? C21 C20 H21 118.6 . . ? C17 C20 H21 118.6 . . ? O2 C21 C20 124.23(19) . . ? O2 C21 C23 116.04(19) . . ? C20 C21 C23 119.73(19) . . ? O2 C22 H16 109.5 . . ? O2 C22 H15 109.5 . . ? H16 C22 H15 109.5 . . ? O2 C22 H14 109.5 . . ? H16 C22 H14 109.5 . . ? H15 C22 H14 109.5 . . ? O3 C23 C25 124.70(19) . . ? O3 C23 C21 116.72(19) . . ? C25 C23 C21 118.6(2) . . ? O3 C24 H17 109.5 . . ? O3 C24 H19 109.5 . . ? H17 C24 H19 109.5 . . ? O3 C24 H18 109.5 . . ? H17 C24 H18 109.5 . . ? H19 C24 H18 109.5 . . ? C23 C25 C16 121.6(2) . . ? C23 C25 H20 119.2 . . ? C16 C25 H20 119.2 . . ? 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 1.4343(17) . ? S1 O4 1.4347(17) . ? S1 C4 1.769(2) . ? S1 C5 1.814(2) . ? O1 C15 1.218(3) . ? O2 C21 1.365(3) . ? O2 C22 1.431(3) . ? O3 C23 1.369(3) . ? O3 C24 1.431(2) . ? C1 C13 1.377(4) . ? C1 C2 1.384(4) . ? C1 H1 0.9500 . ? C2 C3 1.382(3) . ? C2 H22 0.9500 . ? C3 C4 1.393(3) . ? C3 H23 0.9500 . ? C4 C14 1.379(3) . ? C5 C15 1.522(3) . ? C5 C6 1.526(3) . ? C5 H4 1.0000 . ? C6 C7 1.534(3) . ? C6 H5 0.9900 . ? C6 H6 0.9900 . ? C7 C8 1.534(3) . ? C7 H7 0.9900 . ? C7 H8 0.9900 . ? C8 C9 1.521(3) . ? C8 C17 1.537(3) . ? C8 H13 1.0000 . ? C9 C10 1.390(3) . ? C9 C19 1.390(3) . ? C10 C11 1.385(3) . ? C10 H9 0.9500 . ? C11 C12 1.382(3) . ? C11 H12 0.9500 . ? C12 C18 1.385(3) . ? C12 H2 0.9500 . ? C13 C14 1.388(3) . ? C13 H3 0.9500 . ? C14 H24 0.9500 . ? C15 C16 1.490(3) . ? C16 C17 1.402(3) . ? C16 C25 1.405(3) . ? C17 C20 1.401(3) . ? C18 C19 1.386(3) . ? C18 H11 0.9500 . ? C19 H10 0.9500 . ? C20 C21 1.380(3) . ? C20 H21 0.9500 . ? C21 C23 1.403(3) . ? C22 H16 0.9800 . ? C22 H15 0.9800 . ? C22 H14 0.9800 . ? C23 C25 1.377(3) . ? C24 H17 0.9800 . ? C24 H19 0.9800 . ? C24 H18 0.9800 . ? C25 H20 0.9500 . ?