#------------------------------------------------------------------------------ #$Date: 2024-04-26 03:32:41 +0300 (Fri, 26 Apr 2024) $ #$Revision: 291361 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159919.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_7159919 loop_ _publ_author_name 'Roy, Barnali' 'Kuila, Puspendu' 'Jha, Sangam' 'Sarkar, Debayan' _publ_section_title ; BF3·Et2O Assisted Synthesis of Sulfinylated Spiro[5.5]trienones from Biaryl ynones ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D3OB02010J _journal_year 2024 _chemical_formula_moiety 'C27 H17 F O3 S' _chemical_formula_sum 'C27 H17 F O3 S' _chemical_formula_weight 440.46 _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' _atom_sites_solution_hydrogens geom _audit_creation_date 2022-11-11 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2022-12-13 deposited with the CCDC. 2024-04-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.4241(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.85251(18) _cell_length_b 9.76803(17) _cell_length_c 20.3019(3) _cell_measurement_reflns_used 13869 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 67.8010 _cell_measurement_theta_min 4.1250 _cell_volume 2123.11(6) _computing_cell_refinement 'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix3000 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -72.00 31.00 0.50 0.25 -- -40.33 90.00 104.00 206 2 \w -21.00 72.00 0.50 0.25 -- 40.33 -90.00 -10.00 186 3 \w -81.00 -11.00 0.50 1.00 -- -82.50 90.00 104.00 140 4 \w 100.00 168.00 0.50 1.00 -- 96.67 90.00 104.00 136 5 \w 26.00 106.00 0.50 1.00 -- 96.67 -90.00 -10.00 160 6 \w -24.00 35.00 0.50 0.25 -- -40.33 12.00 30.00 118 7 \w -78.00 4.00 0.50 0.25 -- -40.33 104.00 0.00 164 8 \w -24.00 35.00 0.50 0.25 -- -40.33 12.00 -90.00 118 9 \w -31.00 30.00 0.50 0.25 -- -40.33 25.00 150.00 122 10 \w -24.00 35.00 0.50 0.25 -- -40.33 12.00 0.00 118 11 \w -24.00 35.00 0.50 0.25 -- -40.33 12.00-120.00 118 12 \w 41.00 99.00 0.50 0.25 -- 40.33-138.00 30.00 116 13 \w -30.00 31.00 0.50 0.25 -- 40.33 -25.00 0.00 122 14 \w -47.00 -15.00 0.50 1.00 -- -82.50 42.00-120.00 64 15 \w -153.00 -78.00 0.50 1.00 -- -82.50 -90.00 -10.00 150 16 \w -83.00 -14.00 0.50 1.00 -- -82.50 68.00 -60.00 138 17 \w 22.00 106.00 0.50 1.00 -- 96.67 -96.00 60.00 168 18 \w 30.00 57.00 0.50 1.00 -- 96.67 -50.00-180.00 54 19 \w 29.00 83.00 0.50 1.00 -- 96.67 -68.00 -90.00 108 20 \w 30.00 57.00 0.50 1.00 -- 96.67 -50.00 90.00 54 21 \w 73.00 165.00 0.50 1.00 -- 96.67 68.00 30.00 184 22 \w 73.00 165.00 0.50 1.00 -- 96.67 68.00 150.00 184 23 \w 30.00 57.00 0.50 1.00 -- 96.67 -50.00 60.00 54 24 \w 78.00 163.00 0.50 1.00 -- 96.67 50.00-150.00 170 25 \w 105.00 170.00 0.50 1.00 -- 96.67 96.00 120.00 130 26 \w 99.00 164.00 0.50 1.00 -- 96.67 117.00 30.00 130 27 \w 29.00 83.00 0.50 1.00 -- 96.67 -68.00 60.00 108 28 \w 29.00 68.00 0.50 1.00 -- 96.67 -59.00 60.00 78 29 \w 29.00 68.00 0.50 1.00 -- 96.67 -59.00 120.00 78 30 \w 30.00 57.00 0.50 1.00 -- 96.67 -50.00-150.00 54 31 \w 82.00 167.00 0.50 1.00 -- 96.67 25.00-180.00 170 32 \w 30.00 57.00 0.50 1.00 -- 96.67 -50.00 0.00 54 33 \w 30.00 57.00 0.50 1.00 -- 96.67 -50.00 150.00 54 34 \w 29.00 68.00 0.50 1.00 -- 96.67 -59.00 0.00 78 35 \w 30.00 109.00 0.50 1.00 -- 96.67-117.00-150.00 158 36 \w -107.00 -21.00 0.50 0.25 -- -40.33 -50.00 -90.00 172 37 \w -108.00 -17.00 0.50 0.25 -- -40.33 -64.00-150.00 182 38 \w -109.00 -13.00 0.50 0.25 -- -40.33 -77.00 120.00 192 39 \w -109.00 -13.00 0.50 0.25 -- -40.33 -77.00 90.00 192 40 \w -109.00 -13.00 0.50 0.25 -- -40.33 -77.00-180.00 192 41 \w -108.00 -17.00 0.50 0.25 -- -40.33 -64.00 0.00 182 42 \w -109.00 -13.00 0.50 0.25 -- -40.33 -77.00 -90.00 192 43 \w 14.00 109.00 0.50 0.25 -- 40.33 77.00 -30.00 190 44 \w 14.00 109.00 0.50 0.25 -- 40.33 77.00 30.00 190 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix3000' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0956350000 _diffrn_orient_matrix_UB_12 0.0984886000 _diffrn_orient_matrix_UB_13 0.0227177000 _diffrn_orient_matrix_UB_21 0.0249191000 _diffrn_orient_matrix_UB_22 0.1045339000 _diffrn_orient_matrix_UB_23 -0.0531968000 _diffrn_orient_matrix_UB_31 -0.1045449000 _diffrn_orient_matrix_UB_32 -0.0651344000 _diffrn_orient_matrix_UB_33 -0.0507273000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0917 _diffrn_reflns_av_unetI/netI 0.0386 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 21307 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 68.208 _diffrn_reflns_theta_min 4.352 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.661 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.75979 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.378 _exptl_crystal_F_000 912 _refine_diff_density_max 0.823 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 3859 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.078 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0587 _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^)+(0.1039P)^2^+1.2083P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1719 _refine_ls_wR_factor_ref 0.1771 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3375 _reflns_number_total 3859 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ob02010j2.cif _cod_data_source_block sj-c_auto _cod_database_code 7159919 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C H O S F' _chemical_oxdiff_usercomment '100 K' _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. ; _reflns_odcompleteness_completeness 99.98 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C11(H11), C6(H6), C8(H8), C15(H15), C9(H9), C32(H32), C14(H14), C12(H12), C18(H18), C21(H21), C19(H19), C22(H22), C31(H31), C7(H7), C30(H30), C28(H28), C29(H29) ; _shelx_res_file ; TITL sj-c_auto.res created by SHELXL-2018/3 at 18:40:20 on 11-Nov-2022 CELL 1.54184 10.852508 9.768035 20.301853 90 99.4241 90 ZERR 4 0.00018 0.000168 0.000334 0 0.0017 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F O S UNIT 108 68 4 12 4 L.S. 10 PLAN 1 TEMP -173 CONF MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.103900 1.208300 FVAR 4.12137 S24 5 -0.012724 0.265934 0.522187 11.00000 0.03848 0.04775 = 0.03742 -0.00272 0.00858 0.00191 F23 3 -0.556818 0.188413 0.476775 11.00000 0.04248 0.09163 = 0.05601 -0.00331 -0.00254 -0.02489 O26 4 0.212469 0.411867 0.601815 11.00000 0.02805 0.05115 = 0.04265 0.00548 0.00866 0.00427 O25 4 0.051097 0.334766 0.472553 11.00000 0.05291 0.05284 = 0.04541 0.00336 0.01133 0.00129 O16 4 -0.453953 0.609478 0.737619 11.00000 0.03595 0.06447 = 0.07858 -0.01064 0.02465 -0.00126 C1 1 -0.120102 0.510757 0.671857 11.00000 0.02683 0.03486 = 0.03117 0.00158 0.00686 0.00097 C2 1 -0.112455 0.409856 0.614755 11.00000 0.03151 0.03293 = 0.02889 0.00384 0.00418 0.00010 C11 1 -0.204127 0.625916 0.643015 11.00000 0.03294 0.03787 = 0.03052 -0.00069 0.00382 0.00226 AFIX 43 H11 2 -0.179218 0.680289 0.608689 11.00000 -1.20000 AFIX 0 C3 1 -0.005054 0.379336 0.594177 11.00000 0.03133 0.03778 = 0.03366 0.00177 0.00567 0.00176 C6 1 0.230434 0.592889 0.710915 11.00000 0.02919 0.04168 = 0.05049 0.00435 0.00251 0.00051 AFIX 43 H6 2 0.305619 0.569068 0.695444 11.00000 -1.20000 AFIX 0 C4 1 0.117365 0.441165 0.623307 11.00000 0.02938 0.03760 = 0.03480 0.00889 0.00563 0.00239 C8 1 0.124539 0.716618 0.786717 11.00000 0.04272 0.04440 = 0.04284 -0.00447 -0.00062 -0.00388 AFIX 43 H8 2 0.127195 0.777950 0.823239 11.00000 -1.20000 AFIX 0 C5 1 0.116751 0.536900 0.679640 11.00000 0.02937 0.03525 = 0.03701 0.00699 0.00339 0.00034 C13 1 -0.356777 0.578880 0.716947 11.00000 0.03094 0.04735 = 0.04667 -0.01395 0.01148 -0.00645 C17 1 -0.234835 0.353319 0.580401 11.00000 0.02980 0.03817 = 0.03193 -0.00339 0.00849 0.00000 C10 1 0.006801 0.571111 0.702981 11.00000 0.02865 0.03351 = 0.03396 0.00476 0.00238 -0.00214 C15 1 -0.170425 0.434754 0.726740 11.00000 0.03627 0.03728 = 0.03189 -0.00265 0.00604 -0.00573 AFIX 43 H15 2 -0.123052 0.360576 0.747968 11.00000 -1.20000 AFIX 0 C9 1 0.011450 0.661782 0.756360 11.00000 0.03558 0.03889 = 0.04045 -0.00011 0.00558 -0.00008 AFIX 43 H9 2 -0.063359 0.686206 0.772067 11.00000 -1.20000 AFIX 0 C27 1 0.086447 0.131103 0.559966 11.00000 0.04155 0.04496 = 0.04082 -0.00498 0.00823 -0.00053 C32 1 0.201819 0.109784 0.541618 11.00000 0.04404 0.04663 = 0.05170 -0.00134 0.01488 0.00009 AFIX 43 H32 2 0.232697 0.171037 0.511826 11.00000 -1.20000 AFIX 0 C14 1 -0.277854 0.466580 0.746825 11.00000 0.03969 0.04205 = 0.03776 -0.00433 0.01310 -0.01001 AFIX 43 H14 2 -0.303888 0.414623 0.781644 11.00000 -1.20000 AFIX 0 C12 1 -0.312561 0.655445 0.663479 11.00000 0.03266 0.04295 = 0.03942 -0.00784 0.00005 0.00378 AFIX 43 H12 2 -0.362157 0.728376 0.642576 11.00000 -1.20000 AFIX 0 C18 1 -0.292078 0.414217 0.521190 11.00000 0.03378 0.04609 = 0.03621 0.00158 0.00502 -0.00070 AFIX 43 H18 2 -0.255745 0.492840 0.504583 11.00000 -1.20000 AFIX 0 C21 1 -0.399290 0.185143 0.570697 11.00000 0.04820 0.05801 = 0.04363 -0.00069 0.00930 -0.01981 AFIX 43 H21 2 -0.437242 0.107650 0.587349 11.00000 -1.20000 AFIX 0 C19 1 -0.402604 0.359986 0.486258 11.00000 0.03522 0.05641 = 0.03925 -0.00109 0.00154 0.00268 AFIX 43 H19 2 -0.442764 0.400407 0.445825 11.00000 -1.20000 AFIX 0 C22 1 -0.288748 0.239915 0.605157 11.00000 0.04346 0.04826 = 0.03468 0.00072 0.00456 -0.00820 AFIX 43 H22 2 -0.250129 0.199275 0.645855 11.00000 -1.20000 AFIX 0 C31 1 0.272475 -0.002996 0.567439 11.00000 0.04463 0.04778 = 0.06279 -0.00453 0.01641 0.00381 AFIX 43 H31 2 0.352582 -0.018102 0.555682 11.00000 -1.20000 AFIX 0 C20 1 -0.451491 0.246279 0.512199 11.00000 0.03240 0.06705 = 0.04104 -0.00814 0.00516 -0.01124 C7 1 0.234285 0.681394 0.763434 11.00000 0.03463 0.04730 = 0.05430 0.00081 -0.00473 -0.00561 AFIX 43 H7 2 0.311825 0.718909 0.784072 11.00000 -1.20000 AFIX 0 C30 1 0.226794 -0.092293 0.609773 11.00000 0.05980 0.04286 = 0.06263 -0.00243 0.01067 0.00428 AFIX 43 H30 2 0.275324 -0.169175 0.626919 11.00000 -1.20000 AFIX 0 C28 1 0.039060 0.039948 0.602268 11.00000 0.04770 0.05305 = 0.05345 0.00026 0.01446 -0.00514 AFIX 43 H28 2 -0.041550 0.053873 0.613591 11.00000 -1.20000 AFIX 0 C29 1 0.110667 -0.071157 0.627641 11.00000 0.06020 0.04890 = 0.05842 0.00592 0.01534 -0.00554 AFIX 43 H29 2 0.080042 -0.132871 0.657321 11.00000 -1.20000 AFIX 0 HKLF 4 REM REM wR2 = 0.1771, GooF = S = 1.078, Restrained GooF = 1.078 for all data REM R1 = 0.0587 for 3375 Fo > 4sig(Fo) and 0.0637 for all 3859 data REM 289 parameters refined using 0 restraints END WGHT 0.1039 1.2083 REM Highest difference peak 0.823, deepest hole -0.503, 1-sigma level 0.067 Q1 1 0.0525 0.3215 0.5262 11.00000 0.05 0.82 ; _shelx_res_checksum 52945 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.291 _oxdiff_exptl_absorpt_empirical_full_min 0.793 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 S24 S -0.01272(6) 0.26593(7) 0.52219(3) 0.0410(2) Uani 1 1 d . . . . . F23 F -0.55682(16) 0.1884(2) 0.47678(9) 0.0646(5) Uani 1 1 d . . . . . O26 O 0.21247(15) 0.41187(19) 0.60181(9) 0.0403(4) Uani 1 1 d . . . . . O25 O 0.05110(19) 0.3348(2) 0.47255(10) 0.0500(5) Uani 1 1 d . . . . . O16 O -0.45395(18) 0.6095(2) 0.73762(12) 0.0580(6) Uani 1 1 d . . . . . C1 C -0.1201(2) 0.5108(2) 0.67186(11) 0.0307(5) Uani 1 1 d . . . . . C2 C -0.1125(2) 0.4099(2) 0.61475(11) 0.0312(5) Uani 1 1 d . . . . . C11 C -0.2041(2) 0.6259(3) 0.64301(11) 0.0339(5) Uani 1 1 d . . . . . H11 H -0.179218 0.680289 0.608689 0.041 Uiso 1 1 calc R U . . . C3 C -0.0051(2) 0.3793(2) 0.59418(11) 0.0342(5) Uani 1 1 d . . . . . C6 C 0.2304(2) 0.5929(3) 0.71092(14) 0.0409(6) Uani 1 1 d . . . . . H6 H 0.305619 0.569068 0.695444 0.049 Uiso 1 1 calc R U . . . C4 C 0.1174(2) 0.4412(2) 0.62331(12) 0.0339(5) Uani 1 1 d . . . . . C8 C 0.1245(3) 0.7166(3) 0.78672(14) 0.0442(6) Uani 1 1 d . . . . . H8 H 0.127195 0.777950 0.823239 0.053 Uiso 1 1 calc R U . . . C5 C 0.1168(2) 0.5369(2) 0.67964(12) 0.0341(5) Uani 1 1 d . . . . . C13 C -0.3568(2) 0.5789(3) 0.71695(13) 0.0411(6) Uani 1 1 d . . . . . C17 C -0.2348(2) 0.3533(2) 0.58040(11) 0.0329(5) Uani 1 1 d . . . . . C10 C 0.0068(2) 0.5711(2) 0.70298(12) 0.0323(5) Uani 1 1 d . . . . . C15 C -0.1704(2) 0.4348(3) 0.72674(12) 0.0351(5) Uani 1 1 d . . . . . H15 H -0.123052 0.360576 0.747968 0.042 Uiso 1 1 calc R U . . . C9 C 0.0114(2) 0.6618(3) 0.75636(13) 0.0384(6) Uani 1 1 d . . . . . H9 H -0.063359 0.686206 0.772067 0.046 Uiso 1 1 calc R U . . . C27 C 0.0864(2) 0.1311(3) 0.55997(13) 0.0423(6) Uani 1 1 d . . . . . C32 C 0.2018(3) 0.1098(3) 0.54162(15) 0.0467(6) Uani 1 1 d . . . . . H32 H 0.232697 0.171037 0.511826 0.056 Uiso 1 1 calc R U . . . C14 C -0.2779(2) 0.4666(3) 0.74683(12) 0.0391(6) Uani 1 1 d . . . . . H14 H -0.303888 0.414623 0.781644 0.047 Uiso 1 1 calc R U . . . C12 C -0.3126(2) 0.6554(3) 0.66348(13) 0.0390(6) Uani 1 1 d . . . . . H12 H -0.362157 0.728376 0.642576 0.047 Uiso 1 1 calc R U . . . C18 C -0.2921(2) 0.4142(3) 0.52119(12) 0.0388(6) Uani 1 1 d . . . . . H18 H -0.255745 0.492840 0.504583 0.047 Uiso 1 1 calc R U . . . C21 C -0.3993(3) 0.1851(3) 0.57070(14) 0.0497(7) Uani 1 1 d . . . . . H21 H -0.437242 0.107650 0.587349 0.060 Uiso 1 1 calc R U . . . C19 C -0.4026(2) 0.3600(3) 0.48626(13) 0.0441(6) Uani 1 1 d . . . . . H19 H -0.442764 0.400407 0.445825 0.053 Uiso 1 1 calc R U . . . C22 C -0.2887(3) 0.2399(3) 0.60516(13) 0.0423(6) Uani 1 1 d . . . . . H22 H -0.250129 0.199275 0.645855 0.051 Uiso 1 1 calc R U . . . C31 C 0.2725(3) -0.0030(3) 0.56744(15) 0.0509(7) Uani 1 1 d . . . . . H31 H 0.352582 -0.018102 0.555682 0.061 Uiso 1 1 calc R U . . . C20 C -0.4515(2) 0.2463(3) 0.51220(14) 0.0469(7) Uani 1 1 d . . . . . C7 C 0.2343(2) 0.6814(3) 0.76343(15) 0.0468(7) Uani 1 1 d . . . . . H7 H 0.311825 0.718909 0.784072 0.056 Uiso 1 1 calc R U . . . C30 C 0.2268(3) -0.0923(3) 0.60977(17) 0.0550(7) Uani 1 1 d . . . . . H30 H 0.275324 -0.169175 0.626919 0.066 Uiso 1 1 calc R U . . . C28 C 0.0391(3) 0.0399(3) 0.60227(15) 0.0507(7) Uani 1 1 d . . . . . H28 H -0.041550 0.053873 0.613591 0.061 Uiso 1 1 calc R U . . . C29 C 0.1107(3) -0.0712(3) 0.62764(16) 0.0552(7) Uani 1 1 d . . . . . H29 H 0.080042 -0.132871 0.657321 0.066 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 S24 0.0385(4) 0.0478(4) 0.0374(4) -0.0027(3) 0.0086(3) 0.0019(3) F23 0.0425(9) 0.0916(14) 0.0560(10) -0.0033(10) -0.0025(7) -0.0249(9) O26 0.0281(9) 0.0512(10) 0.0427(9) 0.0055(8) 0.0087(7) 0.0043(7) O25 0.0529(12) 0.0528(11) 0.0454(10) 0.0034(9) 0.0113(9) 0.0013(9) O16 0.0359(10) 0.0645(13) 0.0786(14) -0.0106(11) 0.0246(10) -0.0013(9) C1 0.0268(11) 0.0349(12) 0.0312(11) 0.0016(10) 0.0069(9) 0.0010(9) C2 0.0315(12) 0.0329(12) 0.0289(11) 0.0038(9) 0.0042(9) 0.0001(9) C11 0.0329(12) 0.0379(12) 0.0305(11) -0.0007(10) 0.0038(9) 0.0023(10) C3 0.0313(12) 0.0378(12) 0.0337(12) 0.0018(10) 0.0057(9) 0.0018(9) C6 0.0292(12) 0.0417(14) 0.0505(15) 0.0044(11) 0.0025(10) 0.0005(10) C4 0.0294(12) 0.0376(12) 0.0348(11) 0.0089(10) 0.0056(9) 0.0024(9) C8 0.0427(14) 0.0444(14) 0.0428(14) -0.0045(12) -0.0006(11) -0.0039(11) C5 0.0294(12) 0.0353(12) 0.0370(12) 0.0070(10) 0.0034(9) 0.0003(9) C13 0.0309(12) 0.0473(14) 0.0467(14) -0.0140(12) 0.0115(10) -0.0064(10) C17 0.0298(12) 0.0382(12) 0.0319(11) -0.0034(10) 0.0085(9) 0.0000(9) C10 0.0286(11) 0.0335(12) 0.0340(11) 0.0048(9) 0.0024(9) -0.0021(9) C15 0.0363(12) 0.0373(12) 0.0319(11) -0.0027(10) 0.0060(9) -0.0057(10) C9 0.0356(13) 0.0389(13) 0.0405(13) -0.0001(11) 0.0056(10) -0.0001(10) C27 0.0415(14) 0.0450(14) 0.0408(13) -0.0050(11) 0.0082(11) -0.0005(11) C32 0.0440(15) 0.0466(15) 0.0517(15) -0.0013(13) 0.0149(12) 0.0001(12) C14 0.0397(14) 0.0420(14) 0.0378(12) -0.0043(11) 0.0131(10) -0.0100(11) C12 0.0327(12) 0.0430(13) 0.0394(13) -0.0078(11) 0.0000(10) 0.0038(10) C18 0.0338(12) 0.0461(14) 0.0362(12) 0.0016(11) 0.0050(10) -0.0007(10) C21 0.0482(16) 0.0580(17) 0.0436(14) -0.0007(13) 0.0093(12) -0.0198(13) C19 0.0352(13) 0.0564(16) 0.0393(13) -0.0011(12) 0.0015(10) 0.0027(11) C22 0.0435(14) 0.0483(15) 0.0347(13) 0.0007(11) 0.0046(11) -0.0082(11) C31 0.0446(15) 0.0478(15) 0.0628(18) -0.0045(14) 0.0164(13) 0.0038(12) C20 0.0324(13) 0.0671(18) 0.0410(14) -0.0081(13) 0.0052(11) -0.0112(12) C7 0.0346(14) 0.0473(15) 0.0543(16) 0.0008(13) -0.0047(12) -0.0056(11) C30 0.0598(18) 0.0429(15) 0.0626(18) -0.0024(14) 0.0107(14) 0.0043(13) C28 0.0477(16) 0.0531(16) 0.0534(16) 0.0003(13) 0.0145(13) -0.0051(13) C29 0.0602(18) 0.0489(16) 0.0584(17) 0.0059(14) 0.0153(14) -0.0055(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 O25 S24 C3 107.79(12) . . ? O25 S24 C27 108.13(12) . . ? C27 S24 C3 99.09(11) . . ? C2 C1 C10 113.68(19) . . ? C11 C1 C2 106.89(17) . . ? C11 C1 C10 108.58(19) . . ? C11 C1 C15 112.61(19) . . ? C15 C1 C2 108.17(18) . . ? C15 C1 C10 107.03(18) . . ? C3 C2 C1 122.6(2) . . ? C3 C2 C17 121.6(2) . . ? C17 C2 C1 115.74(19) . . ? C1 C11 H11 118.4 . . ? C12 C11 C1 123.1(2) . . ? C12 C11 H11 118.4 . . ? C2 C3 S24 117.30(18) . . ? C2 C3 C4 123.5(2) . . ? C4 C3 S24 118.98(17) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C7 C6 C5 120.8(2) . . ? O26 C4 C3 121.0(2) . . ? O26 C4 C5 122.5(2) . . ? C5 C4 C3 116.5(2) . . ? C9 C8 H8 120.1 . . ? C9 C8 C7 119.8(3) . . ? C7 C8 H8 120.1 . . ? C6 C5 C4 118.8(2) . . ? C10 C5 C6 119.4(2) . . ? C10 C5 C4 121.8(2) . . ? O16 C13 C14 121.1(3) . . ? O16 C13 C12 122.1(3) . . ? C14 C13 C12 116.8(2) . . ? C18 C17 C2 118.7(2) . . ? C22 C17 C2 121.3(2) . . ? C22 C17 C18 120.0(2) . . ? C5 C10 C1 121.9(2) . . ? C9 C10 C1 118.7(2) . . ? C9 C10 C5 119.5(2) . . ? C1 C15 H15 118.3 . . ? C14 C15 C1 123.4(2) . . ? C14 C15 H15 118.3 . . ? C8 C9 C10 120.5(2) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C32 C27 S24 120.2(2) . . ? C32 C27 C28 120.9(3) . . ? C28 C27 S24 118.5(2) . . ? C27 C32 H32 120.5 . . ? C27 C32 C31 119.0(3) . . ? C31 C32 H32 120.5 . . ? C13 C14 H14 119.0 . . ? C15 C14 C13 122.0(2) . . ? C15 C14 H14 119.0 . . ? C11 C12 C13 122.1(2) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C17 C18 H18 119.9 . . ? C17 C18 C19 120.1(2) . . ? C19 C18 H18 119.9 . . ? C22 C21 H21 121.0 . . ? C20 C21 H21 121.0 . . ? C20 C21 C22 118.0(3) . . ? C18 C19 H19 121.1 . . ? C20 C19 C18 117.8(2) . . ? C20 C19 H19 121.1 . . ? C17 C22 C21 120.3(2) . . ? C17 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C32 C31 H31 119.8 . . ? C30 C31 C32 120.3(3) . . ? C30 C31 H31 119.8 . . ? F23 C20 C19 118.3(2) . . ? C21 C20 F23 117.9(3) . . ? C21 C20 C19 123.8(2) . . ? C6 C7 C8 120.1(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C31 C30 H30 119.8 . . ? C31 C30 C29 120.5(3) . . ? C29 C30 H30 119.8 . . ? C27 C28 H28 120.4 . . ? C29 C28 C27 119.3(3) . . ? C29 C28 H28 120.4 . . ? C30 C29 C28 120.0(3) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? 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 S24 O25 1.475(2) . ? S24 C3 1.825(2) . ? S24 C27 1.792(3) . ? F23 C20 1.369(3) . ? O26 C4 1.219(3) . ? O16 C13 1.234(3) . ? C1 C2 1.534(3) . ? C1 C11 1.505(3) . ? C1 C10 1.536(3) . ? C1 C15 1.513(3) . ? C2 C3 1.335(3) . ? C2 C17 1.501(3) . ? C11 H11 0.9500 . ? C11 C12 1.342(3) . ? C3 C4 1.491(3) . ? C6 H6 0.9500 . ? C6 C5 1.403(3) . ? C6 C7 1.368(4) . ? C4 C5 1.478(4) . ? C8 H8 0.9500 . ? C8 C9 1.388(4) . ? C8 C7 1.395(4) . ? C5 C10 1.395(3) . ? C13 C14 1.461(4) . ? C13 C12 1.462(4) . ? C17 C18 1.393(4) . ? C17 C22 1.385(4) . ? C10 C9 1.394(4) . ? C15 H15 0.9500 . ? C15 C14 1.333(4) . ? C9 H9 0.9500 . ? C27 C32 1.379(4) . ? C27 C28 1.393(4) . ? C32 H32 0.9500 . ? C32 C31 1.395(4) . ? C14 H14 0.9500 . ? C12 H12 0.9500 . ? C18 H18 0.9500 . ? C18 C19 1.394(4) . ? C21 H21 0.9500 . ? C21 C22 1.393(4) . ? C21 C20 1.367(4) . ? C19 H19 0.9500 . ? C19 C20 1.373(4) . ? C22 H22 0.9500 . ? C31 H31 0.9500 . ? C31 C30 1.373(4) . ? C7 H7 0.9500 . ? C30 H30 0.9500 . ? C30 C29 1.383(4) . ? C28 H28 0.9500 . ? C28 C29 1.384(4) . ? C29 H29 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S24 C3 C4 O26 -3.6(3) . . . . ? S24 C3 C4 C5 177.38(16) . . . . ? S24 C27 C32 C31 -174.5(2) . . . . ? S24 C27 C28 C29 174.9(2) . . . . ? O26 C4 C5 C6 -2.0(4) . . . . ? O26 C4 C5 C10 179.0(2) . . . . ? O25 S24 C3 C2 126.5(2) . . . . ? O25 S24 C3 C4 -48.7(2) . . . . ? O25 S24 C27 C32 1.3(3) . . . . ? O25 S24 C27 C28 -171.7(2) . . . . ? O16 C13 C14 C15 -177.7(2) . . . . ? O16 C13 C12 C11 177.0(2) . . . . ? C1 C2 C3 S24 -176.16(16) . . . . ? C1 C2 C3 C4 -1.1(4) . . . . ? C1 C2 C17 C18 97.1(3) . . . . ? C1 C2 C17 C22 -85.2(3) . . . . ? C1 C11 C12 C13 1.3(4) . . . . ? C1 C10 C9 C8 178.8(2) . . . . ? C1 C15 C14 C13 0.1(4) . . . . ? C2 C1 C11 C12 117.7(2) . . . . ? C2 C1 C10 C5 0.9(3) . . . . ? C2 C1 C10 C9 -178.6(2) . . . . ? C2 C1 C15 C14 -117.6(2) . . . . ? C2 C3 C4 O26 -178.5(2) . . . . ? C2 C3 C4 C5 2.4(3) . . . . ? C2 C17 C18 C19 176.8(2) . . . . ? C2 C17 C22 C21 -176.9(2) . . . . ? C11 C1 C2 C3 119.2(2) . . . . ? C11 C1 C2 C17 -57.3(2) . . . . ? C11 C1 C10 C5 -117.9(2) . . . . ? C11 C1 C10 C9 62.6(3) . . . . ? C11 C1 C15 C14 0.3(3) . . . . ? C3 S24 C27 C32 -110.9(2) . . . . ? C3 S24 C27 C28 76.1(2) . . . . ? C3 C2 C17 C18 -79.4(3) . . . . ? C3 C2 C17 C22 98.3(3) . . . . ? C3 C4 C5 C6 177.0(2) . . . . ? C3 C4 C5 C10 -2.0(3) . . . . ? C6 C5 C10 C1 -178.6(2) . . . . ? C6 C5 C10 C9 0.9(3) . . . . ? C4 C5 C10 C1 0.4(3) . . . . ? C4 C5 C10 C9 179.9(2) . . . . ? C5 C6 C7 C8 0.3(4) . . . . ? C5 C10 C9 C8 -0.8(4) . . . . ? C17 C2 C3 S24 0.1(3) . . . . ? C17 C2 C3 C4 175.2(2) . . . . ? C17 C18 C19 C20 0.0(4) . . . . ? C10 C1 C2 C3 -0.6(3) . . . . ? C10 C1 C2 C17 -177.08(19) . . . . ? C10 C1 C11 C12 -119.3(2) . . . . ? C10 C1 C15 C14 119.5(3) . . . . ? C15 C1 C2 C3 -119.3(2) . . . . ? C15 C1 C2 C17 64.2(2) . . . . ? C15 C1 C11 C12 -1.0(3) . . . . ? C15 C1 C10 C5 120.3(2) . . . . ? C15 C1 C10 C9 -59.2(3) . . . . ? C9 C8 C7 C6 -0.1(4) . . . . ? C27 S24 C3 C2 -121.0(2) . . . . ? C27 S24 C3 C4 63.7(2) . . . . ? C27 C32 C31 C30 0.9(4) . . . . ? C27 C28 C29 C30 -1.4(5) . . . . ? C32 C27 C28 C29 1.9(4) . . . . ? C32 C31 C30 C29 -0.4(5) . . . . ? C14 C13 C12 C11 -0.8(3) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C18 C17 C22 C21 0.8(4) . . . . ? C18 C19 C20 F23 -177.0(2) . . . . ? C18 C19 C20 C21 1.2(5) . . . . ? C22 C17 C18 C19 -1.0(4) . . . . ? C22 C21 C20 F23 176.9(3) . . . . ? C22 C21 C20 C19 -1.4(5) . . . . ? C31 C30 C29 C28 0.6(5) . . . . ? C20 C21 C22 C17 0.3(4) . . . . ? C7 C6 C5 C4 -179.7(2) . . . . ? C7 C6 C5 C10 -0.6(4) . . . . ? C7 C8 C9 C10 0.4(4) . . . . ? C28 C27 C32 C31 -1.6(4) . . . . ?