#------------------------------------------------------------------------------ #$Date: 2026-06-05 20:25:43 +0100 (Fri, 05 Jun 2026) $ #$Revision: 306458 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064372.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_7064372 loop_ _publ_author_name 'Xu, Jiefang' 'Fan, Haoqun' 'Cao, Feng' 'Yang, Xiaohu' 'Huang, Chunyan' _publ_section_title ; Photo-induced tandem cyclization of alkynes with sodium sulfinates to access sulfonated exocyclic alkenes ; _journal_issue 17 _journal_name_full 'New Journal of Chemistry' _journal_page_first 7515 _journal_page_last 7519 _journal_paper_doi 10.1039/D6NJ00474A _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C24 H15 Br O2 S2, C3 H7' _chemical_formula_sum 'C27 H22 Br O2 S2' _chemical_formula_weight 522.47 _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_date 2025-04-30 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2025-05-07 deposited with the CCDC. 2026-04-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.9130(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.9257(3) _cell_length_b 16.5073(9) _cell_length_c 24.3620(12) _cell_measurement_reflns_used 6795 _cell_measurement_temperature 293.15 _cell_measurement_theta_max 24.52 _cell_measurement_theta_min 2.61 _cell_volume 2381.7(2) _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)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293.15 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.995 _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 0.1201 _diffrn_reflns_av_unetI/netI 0.0582 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 68963 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.607 _diffrn_reflns_theta_min 2.606 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.924 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1867 before and 0.0828 after correction. The Ratio of minimum to maximum transmission is 0.6786. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.457 _exptl_crystal_description block _exptl_crystal_F_000 1068 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.666 _refine_diff_density_min -0.529 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 319 _refine_ls_number_reflns 5510 _refine_ls_number_restraints 69 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0449 _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^)+(0.0390P)^2^+0.9927P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0955 _refine_ls_wR_factor_ref 0.1136 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3467 _reflns_number_total 5510 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00474a2.cif _cod_data_source_block 1_a _cod_depositor_comments 'Adding full bibliography for 7064372.cif.' _cod_database_code 7064372 _shelx_shelxl_version_number 2018/3 _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_max 0.831 _shelx_estimated_absorpt_t_min 0.711 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints C25 \\sim C26 \\sim C27 \\sim C25A \\sim C26A \\sim C27A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A 3. Same fragment restrains {C25A, C26A, C27A} sigma for 1-2: 0.01, 1-3: 0.02 as in {C25, C26, C27} 4. Others Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=Sof(C26A)=Sof(H26C)=Sof(H26D)= Sof(C27A)=Sof(H27C)=Sof(H27D)=1-FVAR(1) Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)= Sof(H27A)=Sof(H27B)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C26(H26A,H26B), C27(H27A,H27B), C26A(H26C,H26D), C27A(H27C,H27D) 5.b Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24) 5.c Idealised Me refined as rotating group: C25(H25A,H25B,H25C), C25A(H25D,H25E,H25F) ; _shelx_res_file ; TITL 1_a.res in P2(1)/c 1_a.res created by SHELXL-2018/3 at 22:17:04 on 30-Apr-2025 REM Old TITL 1 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.300, Rweak 0.041, Alpha 0.042 REM 0.349 for 187 systematic absences, Orientation as input REM Formula found by SHELXT: C25 N O2 S3 CELL 0.71073 5.9257 16.5073 24.362 90 91.913 90 ZERR 4 0.0003 0.0009 0.0012 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br O S UNIT 108 88 4 8 8 SIMU 0.01 0.02 2 C25 C26 C27 C25A C26A C27A L.S. 10 PLAN 20 SIZE 0.1 0.1 0.19 TEMP 20 CONF LIST 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.039000 0.992700 FVAR 0.68161 0.69155 BR1 3 0.297770 0.169627 0.447363 11.00000 0.07482 0.11748 = 0.05700 -0.00124 0.01608 -0.00693 S1 5 0.810099 0.207988 0.222175 11.00000 0.05106 0.05043 = 0.05022 0.00231 0.00591 0.01424 S2 5 0.401807 0.189696 0.126723 11.00000 0.06190 0.04429 = 0.05192 -0.00325 0.00505 -0.00402 O1 4 1.039873 0.231502 0.233487 11.00000 0.04294 0.07876 = 0.07270 0.01097 0.00521 0.01660 O2 4 0.764351 0.138129 0.188614 11.00000 0.08416 0.04997 = 0.05581 -0.00521 0.00648 0.02066 C1 1 0.500977 0.283900 0.154308 11.00000 0.04278 0.04209 = 0.04110 0.00122 0.00839 -0.00039 C2 1 0.368030 0.350446 0.128611 11.00000 0.04454 0.04775 = 0.04127 0.00358 0.00543 -0.00155 C3 1 0.399415 0.432835 0.132319 11.00000 0.04852 0.04474 = 0.05701 0.00393 -0.00120 -0.00283 AFIX 43 H3 2 0.521516 0.454404 0.152352 11.00000 -1.20000 AFIX 0 C4 1 0.239841 0.484113 0.104646 11.00000 0.07648 0.04997 = 0.07253 0.01305 -0.00499 0.00369 AFIX 43 H4 2 0.260228 0.539892 0.106881 11.00000 -1.20000 AFIX 0 C5 1 0.057742 0.454932 0.074897 11.00000 0.06328 0.06888 = 0.05929 0.01594 -0.00470 0.01085 AFIX 43 H5 2 -0.044593 0.490738 0.058263 11.00000 -1.20000 AFIX 0 C6 1 0.024822 0.371047 0.069392 11.00000 0.05069 0.07222 = 0.04216 0.00594 0.00251 -0.00027 C7 1 0.185315 0.320926 0.095942 11.00000 0.04342 0.05228 = 0.03638 0.00071 0.00388 -0.00498 C8 1 0.173791 0.236182 0.091660 11.00000 0.05343 0.05905 = 0.03963 -0.00219 0.00751 -0.00886 C9 1 -0.001445 0.200491 0.062311 11.00000 0.06788 0.07224 = 0.04992 -0.00642 0.00400 -0.02310 AFIX 43 H9 2 -0.011644 0.144438 0.059292 11.00000 -1.20000 AFIX 0 C10 1 -0.164959 0.251056 0.036963 11.00000 0.05881 0.10720 = 0.04566 -0.00368 -0.00261 -0.02270 AFIX 43 H10 2 -0.285167 0.227203 0.017491 11.00000 -1.20000 AFIX 0 C11 1 -0.155260 0.333005 0.039632 11.00000 0.05148 0.09906 = 0.04427 0.00351 -0.00306 -0.00141 AFIX 43 H11 2 -0.266478 0.364164 0.021980 11.00000 -1.20000 AFIX 0 C12 1 0.662140 0.291698 0.194388 11.00000 0.04028 0.04461 = 0.04263 0.00179 0.00339 0.00523 C13 1 0.711044 0.367444 0.225941 11.00000 0.03879 0.04390 = 0.04452 0.00177 -0.00223 0.00671 C14 1 0.912403 0.408732 0.221589 11.00000 0.04363 0.05526 = 0.06391 -0.00524 0.00326 0.00294 AFIX 43 H14 2 1.017207 0.391059 0.196657 11.00000 -1.20000 AFIX 0 C15 1 0.960255 0.475737 0.253656 11.00000 0.04690 0.05743 = 0.08465 -0.00678 -0.00830 -0.00226 AFIX 43 H15 2 1.096205 0.503121 0.250206 11.00000 -1.20000 AFIX 0 C16 1 0.807157 0.501878 0.290597 11.00000 0.06897 0.05578 = 0.06899 -0.01432 -0.01623 0.00712 AFIX 43 H16 2 0.840243 0.546570 0.312673 11.00000 -1.20000 AFIX 0 C17 1 0.604951 0.462301 0.295142 11.00000 0.06715 0.05571 = 0.06212 -0.00679 0.00987 0.01604 AFIX 43 H17 2 0.500310 0.480906 0.319812 11.00000 -1.20000 AFIX 0 C18 1 0.556132 0.394961 0.263243 11.00000 0.04472 0.04780 = 0.06283 -0.00136 0.00817 0.00421 AFIX 43 H18 2 0.419509 0.368031 0.266737 11.00000 -1.20000 AFIX 0 C19 1 0.679541 0.194007 0.285518 11.00000 0.04594 0.04390 = 0.04543 0.00083 -0.00206 0.00725 C20 1 0.770628 0.228645 0.332949 11.00000 0.05008 0.05875 = 0.05630 -0.00324 -0.00173 -0.00484 AFIX 43 H20 2 0.906692 0.256648 0.332275 11.00000 -1.20000 AFIX 0 C21 1 0.657426 0.221222 0.381339 11.00000 0.06395 0.07162 = 0.04773 -0.00950 -0.00283 -0.00545 AFIX 43 H21 2 0.716420 0.244209 0.413582 11.00000 -1.20000 AFIX 0 C22 1 0.456381 0.179447 0.381349 11.00000 0.05258 0.06126 = 0.04773 0.00152 0.00226 0.00735 C23 1 0.365623 0.144589 0.334494 11.00000 0.04673 0.06547 = 0.05829 0.00001 -0.00130 -0.00505 AFIX 43 H23 2 0.229912 0.116376 0.335237 11.00000 -1.20000 AFIX 0 C24 1 0.479086 0.152130 0.286357 11.00000 0.05098 0.05900 = 0.04772 -0.00238 -0.00711 0.00197 AFIX 43 H24 2 0.419874 0.128789 0.254254 11.00000 -1.20000 AFIX 0 SAME 0.01 0.02 C25A C26A C27A PART 1 C25 1 0.156576 0.419592 0.413642 21.00000 0.15015 0.18176 = 0.15095 0.02406 -0.00308 0.02758 AFIX 137 H25A 2 0.168031 0.377762 0.386501 21.00000 -1.50000 H25B 2 0.131434 0.470760 0.395736 21.00000 -1.50000 H25C 2 0.032697 0.407925 0.436790 21.00000 -1.50000 AFIX 0 C26 1 0.382249 0.423412 0.449569 21.00000 0.16020 0.15043 = 0.15858 0.01707 -0.01286 0.03104 AFIX 23 H26A 2 0.390433 0.377335 0.474264 21.00000 -1.20000 H26B 2 0.510680 0.421041 0.425955 21.00000 -1.20000 AFIX 0 C27 1 0.389725 0.497715 0.480959 21.00000 0.15456 0.13911 = 0.16186 0.02127 -0.01591 0.03665 AFIX 23 H27A 2 0.257921 0.500791 0.503433 21.00000 -1.20000 H27B 2 0.385820 0.543591 0.456065 21.00000 -1.20000 AFIX 0 PART 2 C25A 1 0.199731 0.394073 0.417339 -21.00000 0.14742 0.13608 = 0.15051 0.03564 -0.01073 0.04094 AFIX 137 H25D 2 0.184928 0.399641 0.378159 -21.00000 -1.50000 H25E 2 0.056360 0.379501 0.431684 -21.00000 -1.50000 H25F 2 0.308396 0.352611 0.426326 -21.00000 -1.50000 AFIX 0 C26A 1 0.280772 0.476682 0.443279 -21.00000 0.16093 0.14350 = 0.15830 0.01998 -0.01181 0.03583 AFIX 23 H26C 2 0.343114 0.510378 0.414900 -21.00000 -1.20000 H26D 2 0.152110 0.504863 0.457805 -21.00000 -1.20000 AFIX 0 C27A 1 0.448904 0.464932 0.486666 -21.00000 0.16130 0.14551 = 0.16148 0.01523 -0.01528 0.03064 AFIX 23 H27C 2 0.569692 0.432849 0.471820 -21.00000 -1.20000 H27D 2 0.380852 0.432480 0.514891 -21.00000 -1.20000 AFIX 0 HKLF 4 REM 1_a.res in P2(1)/c REM wR2 = 0.1136, GooF = S = 1.023, Restrained GooF = 1.019 for all data REM R1 = 0.0449 for 3467 Fo > 4sig(Fo) and 0.0866 for all 5510 data REM 319 parameters refined using 69 restraints END WGHT 0.0390 0.9914 REM Highest difference peak 0.666, deepest hole -0.529, 1-sigma level 0.050 Q1 1 0.3354 0.2252 0.4504 11.00000 0.05 0.67 Q2 1 0.1606 0.1676 0.4442 11.00000 0.05 0.32 Q3 1 0.6315 0.1567 0.2880 11.00000 0.05 0.23 Q4 1 0.3646 0.1429 0.4426 11.00000 0.05 0.22 Q5 1 0.6481 0.2212 0.3001 11.00000 0.05 0.21 Q6 1 0.2642 0.3353 0.1225 11.00000 0.05 0.20 Q7 1 0.4932 0.2307 0.3803 11.00000 0.05 0.20 Q8 1 0.3772 0.3939 0.1388 11.00000 0.05 0.19 Q9 1 0.6776 0.3401 0.2030 11.00000 0.05 0.19 Q10 1 0.4039 0.3934 0.1206 11.00000 0.05 0.19 Q11 1 0.9706 0.2210 0.2227 11.00000 0.05 0.19 Q12 1 1.0065 0.2041 0.2261 11.00000 0.05 0.17 Q13 1 0.4276 0.3216 0.1461 11.00000 0.05 0.17 Q14 1 0.8084 0.1505 0.2155 11.00000 0.05 0.17 Q15 1 0.9351 0.4182 0.2075 11.00000 0.05 0.17 Q16 1 0.1744 0.2850 0.0931 11.00000 0.05 0.17 Q17 1 0.7235 0.4642 0.3037 11.00000 0.05 0.17 Q18 1 0.9259 0.4627 0.2879 11.00000 0.05 0.17 Q19 1 0.8097 0.3870 0.2222 11.00000 0.05 0.17 Q20 1 0.7508 0.2537 0.2065 11.00000 0.05 0.17 ; _shelx_res_checksum 8114 _olex2_submission_special_instructions 'No special instructions were received' 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 Br1 Br 0.29777(6) 0.16963(3) 0.44736(2) 0.08279(17) Uani 1 1 d . . . . . S1 S 0.81010(12) 0.20799(4) 0.22217(3) 0.0505(2) Uani 1 1 d . . . . . S2 S 0.40181(13) 0.18970(4) 0.12672(3) 0.0526(2) Uani 1 1 d . . . . . O1 O 1.0399(3) 0.23150(14) 0.23349(9) 0.0647(6) Uani 1 1 d . . . . . O2 O 0.7644(4) 0.13813(12) 0.18861(8) 0.0632(6) Uani 1 1 d . . . . . C1 C 0.5010(4) 0.28390(16) 0.15431(10) 0.0418(6) Uani 1 1 d . . . . . C2 C 0.3680(4) 0.35045(16) 0.12861(10) 0.0444(6) Uani 1 1 d . . . . . C3 C 0.3994(5) 0.43283(17) 0.13232(12) 0.0502(7) Uani 1 1 d . . . . . H3 H 0.521516 0.454404 0.152352 0.060 Uiso 1 1 calc R U . . . C4 C 0.2398(6) 0.4841(2) 0.10465(13) 0.0665(9) Uani 1 1 d . . . . . H4 H 0.260228 0.539892 0.106881 0.080 Uiso 1 1 calc R U . . . C5 C 0.0577(5) 0.4549(2) 0.07490(13) 0.0640(8) Uani 1 1 d . . . . . H5 H -0.044593 0.490738 0.058263 0.077 Uiso 1 1 calc R U . . . C6 C 0.0248(5) 0.3710(2) 0.06939(11) 0.0550(7) Uani 1 1 d . . . . . C7 C 0.1853(4) 0.32093(16) 0.09594(10) 0.0440(6) Uani 1 1 d . . . . . C8 C 0.1738(5) 0.23618(18) 0.09166(11) 0.0506(7) Uani 1 1 d . . . . . C9 C -0.0014(5) 0.2005(2) 0.06231(13) 0.0633(9) Uani 1 1 d . . . . . H9 H -0.011644 0.144438 0.059292 0.076 Uiso 1 1 calc R U . . . C10 C -0.1650(5) 0.2511(3) 0.03696(12) 0.0707(10) Uani 1 1 d . . . . . H10 H -0.285167 0.227203 0.017491 0.085 Uiso 1 1 calc R U . . . C11 C -0.1553(5) 0.3330(2) 0.03963(12) 0.0650(9) Uani 1 1 d . . . . . H11 H -0.266478 0.364164 0.021980 0.078 Uiso 1 1 calc R U . . . C12 C 0.6621(4) 0.29170(16) 0.19439(11) 0.0425(6) Uani 1 1 d . . . . . C13 C 0.7110(4) 0.36744(16) 0.22594(10) 0.0425(6) Uani 1 1 d . . . . . C14 C 0.9124(4) 0.40873(18) 0.22159(12) 0.0542(7) Uani 1 1 d . . . . . H14 H 1.017207 0.391059 0.196657 0.065 Uiso 1 1 calc R U . . . C15 C 0.9603(5) 0.4757(2) 0.25366(14) 0.0632(8) Uani 1 1 d . . . . . H15 H 1.096205 0.503121 0.250206 0.076 Uiso 1 1 calc R U . . . C16 C 0.8072(5) 0.5019(2) 0.29060(13) 0.0650(9) Uani 1 1 d . . . . . H16 H 0.840243 0.546570 0.312673 0.078 Uiso 1 1 calc R U . . . C17 C 0.6050(5) 0.46230(19) 0.29514(13) 0.0615(8) Uani 1 1 d . . . . . H17 H 0.500310 0.480906 0.319812 0.074 Uiso 1 1 calc R U . . . C18 C 0.5561(5) 0.39496(17) 0.26324(12) 0.0516(7) Uani 1 1 d . . . . . H18 H 0.419509 0.368031 0.266737 0.062 Uiso 1 1 calc R U . . . C19 C 0.6795(4) 0.19401(16) 0.28552(11) 0.0452(6) Uani 1 1 d . . . . . C20 C 0.7706(5) 0.22865(18) 0.33295(12) 0.0551(7) Uani 1 1 d . . . . . H20 H 0.906692 0.256648 0.332275 0.066 Uiso 1 1 calc R U . . . C21 C 0.6574(5) 0.2212(2) 0.38134(12) 0.0612(8) Uani 1 1 d . . . . . H21 H 0.716420 0.244209 0.413582 0.073 Uiso 1 1 calc R U . . . C22 C 0.4564(5) 0.17945(18) 0.38135(12) 0.0538(7) Uani 1 1 d . . . . . C23 C 0.3656(5) 0.14459(19) 0.33449(12) 0.0569(7) Uani 1 1 d . . . . . H23 H 0.229912 0.116376 0.335237 0.068 Uiso 1 1 calc R U . . . C24 C 0.4791(5) 0.15213(18) 0.28636(12) 0.0528(7) Uani 1 1 d . . . . . H24 H 0.419874 0.128789 0.254254 0.063 Uiso 1 1 calc R U . . . C25 C 0.157(3) 0.4196(9) 0.4136(8) 0.161(5) Uani 0.692(9) 1 d D U P A 1 H25A H 0.168031 0.377762 0.386501 0.242 Uiso 0.692(9) 1 calc R U P A 1 H25B H 0.131434 0.470760 0.395736 0.242 Uiso 0.692(9) 1 calc R U P A 1 H25C H 0.032697 0.407925 0.436790 0.242 Uiso 0.692(9) 1 calc R U P A 1 C26 C 0.3822(17) 0.4234(6) 0.4496(4) 0.157(3) Uani 0.692(9) 1 d D U P A 1 H26A H 0.390433 0.377335 0.474264 0.188 Uiso 0.692(9) 1 calc R U P A 1 H26B H 0.510680 0.421041 0.425955 0.188 Uiso 0.692(9) 1 calc R U P A 1 C27 C 0.3897(19) 0.4977(6) 0.4810(5) 0.152(3) Uani 0.692(9) 1 d D U P A 1 H27A H 0.257921 0.500791 0.503433 0.183 Uiso 0.692(9) 1 calc R U P A 1 H27B H 0.385820 0.543591 0.456065 0.183 Uiso 0.692(9) 1 calc R U P A 1 C25A C 0.200(7) 0.3941(17) 0.4173(18) 0.145(6) Uani 0.308(9) 1 d D U P A 2 H25D H 0.184928 0.399641 0.378159 0.218 Uiso 0.308(9) 1 calc R U P A 2 H25E H 0.056360 0.379501 0.431684 0.218 Uiso 0.308(9) 1 calc R U P A 2 H25F H 0.308396 0.352611 0.426326 0.218 Uiso 0.308(9) 1 calc R U P A 2 C26A C 0.281(4) 0.4767(12) 0.4433(9) 0.155(4) Uani 0.308(9) 1 d D U P A 2 H26C H 0.343114 0.510378 0.414900 0.186 Uiso 0.308(9) 1 calc R U P A 2 H26D H 0.152110 0.504863 0.457805 0.186 Uiso 0.308(9) 1 calc R U P A 2 C27A C 0.449(5) 0.4649(14) 0.4867(11) 0.157(4) Uani 0.308(9) 1 d D U P A 2 H27C H 0.569692 0.432849 0.471820 0.188 Uiso 0.308(9) 1 calc R U P A 2 H27D H 0.380852 0.432480 0.514891 0.188 Uiso 0.308(9) 1 calc R U P A 2 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 Br1 0.0748(3) 0.1175(4) 0.0570(2) -0.0012(2) 0.01608(17) -0.0069(2) S1 0.0511(4) 0.0504(4) 0.0502(4) 0.0023(3) 0.0059(3) 0.0142(3) S2 0.0619(4) 0.0443(4) 0.0519(4) -0.0032(3) 0.0051(3) -0.0040(3) O1 0.0429(11) 0.0788(15) 0.0727(14) 0.0110(12) 0.0052(10) 0.0166(10) O2 0.0842(15) 0.0500(12) 0.0558(12) -0.0052(10) 0.0065(11) 0.0207(11) C1 0.0428(14) 0.0421(15) 0.0411(14) 0.0012(11) 0.0084(11) -0.0004(11) C2 0.0445(14) 0.0478(16) 0.0413(14) 0.0036(12) 0.0054(11) -0.0016(12) C3 0.0485(15) 0.0447(17) 0.0570(17) 0.0039(13) -0.0012(13) -0.0028(13) C4 0.076(2) 0.0500(19) 0.073(2) 0.0131(16) -0.0050(18) 0.0037(16) C5 0.0633(19) 0.069(2) 0.0593(19) 0.0159(16) -0.0047(15) 0.0109(17) C6 0.0507(17) 0.072(2) 0.0422(15) 0.0059(14) 0.0025(13) -0.0003(15) C7 0.0434(14) 0.0523(17) 0.0364(13) 0.0007(12) 0.0039(11) -0.0050(12) C8 0.0534(16) 0.0590(19) 0.0396(14) -0.0022(13) 0.0075(12) -0.0089(14) C9 0.068(2) 0.072(2) 0.0499(17) -0.0064(16) 0.0040(15) -0.0231(17) C10 0.0588(19) 0.107(3) 0.0457(17) -0.0037(19) -0.0026(15) -0.023(2) C11 0.0515(18) 0.099(3) 0.0443(16) 0.0035(17) -0.0031(13) -0.0014(17) C12 0.0403(13) 0.0446(15) 0.0426(14) 0.0018(12) 0.0034(11) 0.0052(11) C13 0.0388(13) 0.0439(15) 0.0445(14) 0.0018(12) -0.0022(11) 0.0067(11) C14 0.0436(15) 0.0553(19) 0.0639(18) -0.0052(15) 0.0033(13) 0.0029(13) C15 0.0469(16) 0.057(2) 0.085(2) -0.0068(17) -0.0083(16) -0.0023(14) C16 0.069(2) 0.056(2) 0.069(2) -0.0143(16) -0.0162(17) 0.0071(16) C17 0.067(2) 0.0557(19) 0.0621(19) -0.0068(15) 0.0099(15) 0.0160(16) C18 0.0447(15) 0.0478(17) 0.0628(18) -0.0014(14) 0.0082(13) 0.0042(12) C19 0.0459(15) 0.0439(15) 0.0454(15) 0.0008(12) -0.0021(12) 0.0073(12) C20 0.0501(16) 0.0588(19) 0.0563(18) -0.0032(15) -0.0017(13) -0.0048(14) C21 0.0639(19) 0.072(2) 0.0477(17) -0.0095(15) -0.0028(14) -0.0054(16) C22 0.0526(17) 0.0613(19) 0.0477(16) 0.0015(14) 0.0023(13) 0.0074(14) C23 0.0467(16) 0.065(2) 0.0583(18) 0.0000(15) -0.0013(13) -0.0050(14) C24 0.0510(16) 0.0590(19) 0.0477(16) -0.0024(14) -0.0071(13) 0.0020(14) C25 0.150(9) 0.182(11) 0.151(8) 0.024(9) -0.003(6) 0.028(8) C26 0.160(7) 0.150(7) 0.159(7) 0.017(6) -0.013(5) 0.031(6) C27 0.155(7) 0.139(8) 0.162(8) 0.021(6) -0.016(6) 0.037(6) C25A 0.147(12) 0.136(12) 0.151(11) 0.036(11) -0.011(10) 0.041(11) C26A 0.161(8) 0.143(8) 0.158(8) 0.020(7) -0.012(7) 0.036(7) C27A 0.161(9) 0.146(9) 0.161(9) 0.015(8) -0.015(7) 0.031(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' Br Br -0.2901 2.4595 '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 O1 S1 O2 119.18(13) . . ? O1 S1 C12 108.61(13) . . ? O1 S1 C19 107.98(13) . . ? O2 S1 C12 109.26(13) . . ? O2 S1 C19 108.26(13) . . ? C12 S1 C19 102.23(12) . . ? C8 S2 C1 92.34(13) . . ? C2 C1 S2 108.88(19) . . ? C12 C1 S2 124.9(2) . . ? C12 C1 C2 126.1(2) . . ? C3 C2 C1 129.6(3) . . ? C3 C2 C7 118.6(3) . . ? C7 C2 C1 111.8(2) . . ? C2 C3 H3 120.9 . . ? C2 C3 C4 118.1(3) . . ? C4 C3 H3 120.9 . . ? C3 C4 H4 118.6 . . ? C5 C4 C3 122.8(3) . . ? C5 C4 H4 118.6 . . ? C4 C5 H5 119.9 . . ? C4 C5 C6 120.2(3) . . ? C6 C5 H5 119.9 . . ? C5 C6 C11 125.9(3) . . ? C7 C6 C5 116.6(3) . . ? C7 C6 C11 117.5(3) . . ? C6 C7 C2 123.6(3) . . ? C6 C7 C8 121.5(3) . . ? C8 C7 C2 114.9(2) . . ? C7 C8 S2 111.4(2) . . ? C9 C8 S2 128.6(3) . . ? C9 C8 C7 120.0(3) . . ? C8 C9 H9 120.9 . . ? C8 C9 C10 118.2(3) . . ? C10 C9 H9 120.9 . . ? C9 C10 H10 118.5 . . ? C11 C10 C9 123.0(3) . . ? C11 C10 H10 118.5 . . ? C6 C11 H11 120.1 . . ? C10 C11 C6 119.8(3) . . ? C10 C11 H11 120.1 . . ? C1 C12 S1 122.4(2) . . ? C1 C12 C13 125.0(2) . . ? C13 C12 S1 111.99(19) . . ? C14 C13 C12 121.9(2) . . ? C14 C13 C18 118.7(3) . . ? C18 C13 C12 119.3(2) . . ? C13 C14 H14 119.5 . . ? C15 C14 C13 121.0(3) . . ? C15 C14 H14 119.5 . . ? C14 C15 H15 120.1 . . ? C16 C15 C14 119.8(3) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.2(3) . . ? C17 C16 H16 119.9 . . ? C16 C17 H17 119.8 . . ? C16 C17 C18 120.3(3) . . ? C18 C17 H17 119.8 . . ? C13 C18 H18 120.0 . . ? C17 C18 C13 120.0(3) . . ? C17 C18 H18 120.0 . . ? C20 C19 S1 120.4(2) . . ? C24 C19 S1 118.9(2) . . ? C24 C19 C20 120.6(3) . . ? C19 C20 H20 120.3 . . ? C21 C20 C19 119.3(3) . . ? C21 C20 H20 120.3 . . ? C20 C21 H21 120.3 . . ? C22 C21 C20 119.3(3) . . ? C22 C21 H21 120.3 . . ? C21 C22 Br1 119.8(2) . . ? C23 C22 Br1 118.6(2) . . ? C23 C22 C21 121.7(3) . . ? C22 C23 H23 120.6 . . ? C22 C23 C24 118.8(3) . . ? C24 C23 H23 120.6 . . ? C19 C24 C23 120.3(3) . . ? C19 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? C25 C26 H26A 109.7 . . ? C25 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? C27 C26 C25 109.8(9) . . ? C27 C26 H26A 109.7 . . ? C27 C26 H26B 109.7 . . ? C26 C27 C27 111.2(10) . 3_666 ? C26 C27 H27A 109.4 . . ? C26 C27 H27B 109.4 . . ? C27 C27 H27A 109.4 3_666 . ? C27 C27 H27B 109.4 3_666 . ? H27A C27 H27B 108.0 . . ? H25D C25A H25E 109.5 . . ? H25D C25A H25F 109.5 . . ? H25E C25A H25F 109.5 . . ? C26A C25A H25D 109.5 . . ? C26A C25A H25E 109.5 . . ? C26A C25A H25F 109.5 . . ? C25A C26A H26C 109.2 . . ? C25A C26A H26D 109.2 . . ? H26C C26A H26D 107.9 . . ? C27A C26A C25A 111.9(13) . . ? C27A C26A H26C 109.2 . . ? C27A C26A H26D 109.2 . . ? C26A C27A C27A 119(2) . 3_666 ? C26A C27A H27C 107.5 . . ? C26A C27A H27D 107.5 . . ? C27A C27A H27C 107.5 3_666 . ? C27A C27A H27D 107.5 3_666 . ? H27C C27A H27D 107.0 . . ? 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 Br1 C22 1.897(3) . ? S1 O1 1.434(2) . ? S1 O2 1.434(2) . ? S1 C12 1.760(3) . ? S1 C19 1.764(3) . ? S2 C1 1.786(3) . ? S2 C8 1.751(3) . ? C1 C2 1.479(4) . ? C1 C12 1.349(4) . ? C2 C3 1.375(4) . ? C2 C7 1.409(4) . ? C3 H3 0.9300 . ? C3 C4 1.422(4) . ? C4 H4 0.9300 . ? C4 C5 1.367(4) . ? C5 H5 0.9300 . ? C5 C6 1.404(4) . ? C6 C7 1.402(4) . ? C6 C11 1.417(4) . ? C7 C8 1.404(4) . ? C8 C9 1.374(4) . ? C9 H9 0.9300 . ? C9 C10 1.406(5) . ? C10 H10 0.9300 . ? C10 C11 1.355(5) . ? C11 H11 0.9300 . ? C12 C13 1.491(4) . ? C13 C14 1.381(4) . ? C13 C18 1.389(3) . ? C14 H14 0.9300 . ? C14 C15 1.378(4) . ? C15 H15 0.9300 . ? C15 C16 1.369(4) . ? C16 H16 0.9300 . ? C16 C17 1.372(4) . ? C17 H17 0.9300 . ? C17 C18 1.381(4) . ? C18 H18 0.9300 . ? C19 C20 1.383(4) . ? C19 C24 1.375(4) . ? C20 H20 0.9300 . ? C20 C21 1.381(4) . ? C21 H21 0.9300 . ? C21 C22 1.377(4) . ? C22 C23 1.372(4) . ? C23 H23 0.9300 . ? C23 C24 1.377(4) . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C25 C26 1.575(12) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 C27 1.445(10) . ? C27 C27 1.579(18) 3_666 ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C25A H25D 0.9600 . ? C25A H25E 0.9600 . ? C25A H25F 0.9600 . ? C25A C26A 1.571(14) . ? C26A H26C 0.9700 . ? C26A H26D 0.9700 . ? C26A C27A 1.441(12) . ? C27A C27A 1.45(4) 3_666 ? C27A H27C 0.9700 . ? C27A H27D 0.9700 . ? 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 Br1 C22 C23 C24 179.4(2) . . . . ? S1 C12 C13 C14 75.2(3) . . . . ? S1 C12 C13 C18 -100.9(3) . . . . ? S1 C19 C20 C21 175.8(2) . . . . ? S1 C19 C24 C23 -175.9(2) . . . . ? S2 C1 C2 C3 -172.0(2) . . . . ? S2 C1 C2 C7 7.8(2) . . . . ? S2 C1 C12 S1 4.0(3) . . . . ? S2 C1 C12 C13 -166.02(19) . . . . ? S2 C8 C9 C10 -179.3(2) . . . . ? O1 S1 C12 C1 143.0(2) . . . . ? O1 S1 C12 C13 -45.8(2) . . . . ? O1 S1 C19 C20 20.0(3) . . . . ? O1 S1 C19 C24 -163.7(2) . . . . ? O2 S1 C12 C1 11.5(3) . . . . ? O2 S1 C12 C13 -177.30(17) . . . . ? O2 S1 C19 C20 150.3(2) . . . . ? O2 S1 C19 C24 -33.4(3) . . . . ? C1 S2 C8 C7 6.0(2) . . . . ? C1 S2 C8 C9 -174.4(3) . . . . ? C1 C2 C3 C4 -177.7(3) . . . . ? C1 C2 C7 C6 176.3(2) . . . . ? C1 C2 C7 C8 -3.6(3) . . . . ? C1 C12 C13 C14 -113.8(3) . . . . ? C1 C12 C13 C18 70.0(4) . . . . ? C2 C1 C12 S1 179.89(18) . . . . ? C2 C1 C12 C13 9.8(4) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C2 C7 C8 S2 -2.5(3) . . . . ? C2 C7 C8 C9 177.9(2) . . . . ? C3 C2 C7 C6 -3.9(4) . . . . ? C3 C2 C7 C8 176.2(2) . . . . ? C3 C4 C5 C6 -1.7(5) . . . . ? C4 C5 C6 C7 0.4(4) . . . . ? C4 C5 C6 C11 -179.7(3) . . . . ? C5 C6 C7 C2 2.4(4) . . . . ? C5 C6 C7 C8 -177.7(3) . . . . ? C5 C6 C11 C10 179.0(3) . . . . ? C6 C7 C8 S2 177.7(2) . . . . ? C6 C7 C8 C9 -2.0(4) . . . . ? C7 C2 C3 C4 2.5(4) . . . . ? C7 C6 C11 C10 -1.1(4) . . . . ? C7 C8 C9 C10 0.3(4) . . . . ? C8 S2 C1 C2 -7.76(18) . . . . ? C8 S2 C1 C12 168.7(2) . . . . ? C8 C9 C10 C11 0.9(5) . . . . ? C9 C10 C11 C6 -0.5(5) . . . . ? C11 C6 C7 C2 -177.5(2) . . . . ? C11 C6 C7 C8 2.4(4) . . . . ? C12 S1 C19 C20 -94.4(2) . . . . ? C12 S1 C19 C24 81.8(2) . . . . ? C12 C1 C2 C3 11.6(4) . . . . ? C12 C1 C2 C7 -168.6(2) . . . . ? C12 C13 C14 C15 -175.9(3) . . . . ? C12 C13 C18 C17 176.2(3) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? C14 C13 C18 C17 -0.1(4) . . . . ? C14 C15 C16 C17 -1.0(5) . . . . ? C15 C16 C17 C18 1.2(5) . . . . ? C16 C17 C18 C13 -0.6(5) . . . . ? C18 C13 C14 C15 0.3(4) . . . . ? C19 S1 C12 C1 -103.1(2) . . . . ? C19 S1 C12 C13 68.2(2) . . . . ? C19 C20 C21 C22 0.0(5) . . . . ? C20 C19 C24 C23 0.4(4) . . . . ? C20 C21 C22 Br1 -179.4(2) . . . . ? C20 C21 C22 C23 0.3(5) . . . . ? C21 C22 C23 C24 -0.3(5) . . . . ? C22 C23 C24 C19 -0.1(4) . . . . ? C24 C19 C20 C21 -0.4(4) . . . . ? C25 C26 C27 C27 178.1(14) . . . 3_666 ? C25A C26A C27A C27A 177(4) . . . 3_666 ?