#------------------------------------------------------------------------------ #$Date: 2019-11-17 15:07:10 +0200 (Sun, 17 Nov 2019) $ #$Revision: 230734 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/61/7156168.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_7156168 loop_ _publ_author_name 'Luo, Shilong' 'Zhang, Nan' 'Wang, Zhen' 'Yan, Hailong' _publ_section_title ; Enantioselective addition of selenosulfonates to \a,\b-unsaturated ketones. ; _journal_issue 16 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 2893 _journal_page_last 2901 _journal_paper_doi 10.1039/c8ob00359a _journal_volume 16 _journal_year 2018 _chemical_absolute_configuration unk _chemical_formula_moiety 'C33 H33 Br O4 S Se' _chemical_formula_sum 'C33 H33 Br O4 S Se' _chemical_formula_weight 684.52 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-01-26 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2018-01-29 deposited with the CCDC. 2018-03-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.199(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.9327(4) _cell_length_b 18.8397(9) _cell_length_c 22.3499(16) _cell_measurement_reflns_used 4051 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.7280 _cell_measurement_theta_min 3.5880 _cell_volume 3287.4(3) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 293.15 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0874 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.958 _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 -82.00 -52.00 0.60 22.50 -- -14.97-178.00 -90.00 50 2 \w -79.00 3.20 0.60 22.50 -- -14.97 -38.00-120.00 137 3 \w -32.00 -5.00 0.60 22.50 -- -14.97 57.00 60.00 45 4 \w 9.00 47.40 0.60 22.50 -- -14.97 57.00 60.00 64 5 \w -5.00 22.00 0.60 22.50 -- -14.97 -99.00-180.00 45 6 \w 40.00 64.60 0.60 22.50 -- 16.69 178.00 -30.00 41 7 \w 4.00 36.40 0.60 22.50 -- 16.53 77.00-120.00 54 8 \w 6.00 19.80 0.60 22.50 -- 16.53 77.00 150.00 23 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0039989000 _diffrn_orient_matrix_UB_12 0.0277756000 _diffrn_orient_matrix_UB_13 0.0216214000 _diffrn_orient_matrix_UB_21 -0.0078595000 _diffrn_orient_matrix_UB_22 0.0254021000 _diffrn_orient_matrix_UB_23 -0.0237462000 _diffrn_orient_matrix_UB_31 -0.0904582000 _diffrn_orient_matrix_UB_32 -0.0009824000 _diffrn_orient_matrix_UB_33 -0.0027180000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_unetI/netI 0.0641 _diffrn_reflns_Laue_measured_fraction_full 0.966 _diffrn_reflns_Laue_measured_fraction_max 0.958 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 19444 _diffrn_reflns_point_group_measured_fraction_full 0.793 _diffrn_reflns_point_group_measured_fraction_max 0.776 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.371 _diffrn_reflns_theta_min 2.981 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 2.454 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.46661 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.383 _exptl_crystal_description block _exptl_crystal_F_000 1392 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.578 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.066 _refine_ls_abs_structure_details ; Flack x determined using 1919 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.042(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 699 _refine_ls_number_reflns 10418 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.0676 _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^)+(0.0585P)^2^+5.9542P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1421 _refine_ls_wR_factor_ref 0.1658 _reflns_Friedel_coverage 0.571 _reflns_Friedel_fraction_full 0.608 _reflns_Friedel_fraction_max 0.582 _reflns_number_gt 6712 _reflns_number_total 10418 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8ob00359a2.cif _cod_data_source_block 180125_s4_wz _cod_depositor_comments 'Adding full bibliography for 7156168.cif.' _cod_database_code 7156168 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula c12h12n2o3 _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 0.579 _shelx_estimated_absorpt_t_min 0.480 _reflns_odcompleteness_completeness 95.79 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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. Restrained distances C18-C19 2.5 with sigma of 0.02 C17-C18 2.5 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C50) = Uanis(C51) = Uanis(C52) Uanis(C17) = Uanis(C18) = Uanis(C19) = Uanis(C33) 4.a Ternary CH refined with riding coordinates: C7(H7), C9(H9), C40(H40), C42(H42) 4.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C41(H41A,H41B) 4.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C31(H31), C32(H32), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C44(H44), C45(H45), C47(H47), C48(H48), C55(H55), C56(H56), C58(H58), C59(H59), C61(H61), C62(H62), C64(H64), C65(H65) 4.d Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C33(H33A,H33B, H33C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C66(H66A, H66B,H66C) ; _shelx_res_file ; 180125_s4_wz.res created by SHELXL-2014/7 TITL 180125_s4_wz_a.res in P2(1) REM Old TITL 180125_s4_wz in P21 #4 REM SHELXT solution in P2(1) REM R1 0.255, Rweak 0.122, Alpha 0.057, Orientation as input REM Flack x = 0.109 ( 0.007 ) from Parsons' quotients REM Formula found by SHELXT: C56 N4 O10 S2 Br4 CELL 0.71073 7.9327 18.8397 22.3499 90 100.199 90 ZERR 4 0.0004 0.0009 0.0016 0 0.005 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Br O S Se UNIT 132 132 4 16 4 4 DFIX 2.5 C18 C19 DFIX 2.5 C17 C18 EADP C50 C51 C52 EADP C17 C18 C19 C33 L.S. 5 PLAN 20 SIZE 0.25 0.3 0.35 TEMP 20 htab conf list 4 fmap 2 ACTA SHEL 999 0.8 REM REM REM WGHT 0.058500 5.954200 FVAR 0.27655 BR1 3 -0.702654 1.018923 0.908510 11.00000 0.12203 0.09519 = 0.23559 0.04203 0.07503 0.05300 SE1 6 -0.226983 0.614800 0.913309 11.00000 0.05269 0.06682 = 0.10413 -0.01524 0.02796 -0.00560 S1 5 0.261810 0.652651 0.844821 11.00000 0.06605 0.06232 = 0.07514 -0.00249 0.03219 -0.00536 O1 4 -0.099672 0.758601 0.942749 11.00000 0.05571 0.04087 = 0.09234 0.00340 0.02107 -0.00015 O2 4 0.066797 0.851915 0.941809 11.00000 0.06460 0.07455 = 0.28818 0.05269 0.05044 0.00012 O3 4 0.269281 0.670070 0.783179 11.00000 0.13695 0.08064 = 0.08708 0.01831 0.06950 0.00967 O4 4 0.364258 0.691444 0.893078 11.00000 0.06208 0.07318 = 0.12048 -0.03375 0.02906 -0.01637 C1 1 -0.190795 0.522559 0.884596 11.00000 0.05926 0.07236 = 0.07626 -0.03407 0.02418 -0.01606 C2 1 -0.252502 0.503796 0.826107 11.00000 0.07458 0.10026 = 0.07615 -0.02286 0.01493 -0.00938 AFIX 43 H2 2 -0.308137 0.537714 0.799452 11.00000 -1.20000 AFIX 0 C3 1 -0.234667 0.435231 0.805054 11.00000 0.11841 0.13675 = 0.13012 -0.07443 0.03251 -0.04052 AFIX 43 H3 2 -0.281749 0.423366 0.765205 11.00000 -1.20000 AFIX 0 C4 1 -0.149805 0.386312 0.842097 11.00000 0.12310 0.09735 = 0.25264 -0.06951 0.06400 -0.01685 AFIX 43 H4 2 -0.129368 0.341548 0.827360 11.00000 -1.20000 AFIX 0 C5 1 -0.092887 0.403052 0.902480 11.00000 0.20516 0.08521 = 0.15341 0.01751 0.01832 0.00371 AFIX 43 H5 2 -0.040717 0.368527 0.929261 11.00000 -1.20000 AFIX 0 C6 1 -0.113166 0.469976 0.922716 11.00000 0.10249 0.06461 = 0.10470 -0.00095 0.00998 0.00078 AFIX 43 H6 2 -0.073582 0.480611 0.963412 11.00000 -1.20000 AFIX 0 C7 1 0.011804 0.648133 0.917711 11.00000 0.03763 0.03699 = 0.05997 -0.00630 0.00894 -0.00177 AFIX 13 H7 2 0.088222 0.610033 0.935877 11.00000 -1.20000 AFIX 0 C8 1 0.042860 0.659528 0.852149 11.00000 0.05912 0.05762 = 0.05298 0.00781 0.00726 0.00553 AFIX 23 H8A 2 0.000876 0.706161 0.838406 11.00000 -1.20000 H8B 2 -0.022795 0.624649 0.825814 11.00000 -1.20000 AFIX 0 C9 1 0.047947 0.711736 0.957238 11.00000 0.05730 0.04302 = 0.05898 0.00902 0.01847 0.00072 AFIX 13 H9 2 0.146496 0.736238 0.945798 11.00000 -1.20000 AFIX 0 C10 1 0.087717 0.698270 1.023738 11.00000 0.08196 0.04523 = 0.05840 0.00283 0.01383 0.00239 C11 1 0.254653 0.694553 1.051210 11.00000 0.12961 0.05072 = 0.06230 -0.00484 0.00090 -0.00324 AFIX 43 H11 2 0.338103 0.701229 1.027299 11.00000 -1.20000 AFIX 0 C12 1 0.307523 0.681590 1.111896 11.00000 0.16976 0.07264 = 0.07656 0.00042 -0.02490 0.00142 AFIX 43 H12 2 0.423048 0.680600 1.129266 11.00000 -1.20000 AFIX 0 C13 1 0.179420 0.669887 1.146600 11.00000 0.29314 0.04239 = 0.05204 0.00442 0.03440 -0.00936 C14 1 0.012897 0.674469 1.120077 11.00000 0.18595 0.11772 = 0.09746 -0.00210 0.06150 -0.00154 AFIX 43 H14 2 -0.072602 0.667727 1.143113 11.00000 -1.20000 AFIX 0 C15 1 -0.029908 0.689076 1.059134 11.00000 0.13923 0.10523 = 0.08166 -0.00386 0.03500 -0.00068 AFIX 43 H15 2 -0.145122 0.692721 1.041783 11.00000 -1.20000 AFIX 0 C16 1 0.251371 0.653592 1.218637 11.00000 0.61463 0.07273 = 0.07314 -0.01920 0.05661 0.07680 C17 1 0.369715 0.716834 1.247735 11.00000 0.55643 0.14337 = 0.10465 0.00153 0.04379 0.05265 AFIX 137 H17A 2 0.477270 0.714846 1.233745 11.00000 -1.50000 H17B 2 0.389243 0.712760 1.291231 11.00000 -1.50000 H17C 2 0.314375 0.761237 1.235868 11.00000 -1.50000 AFIX 0 C18 1 0.082776 0.670961 1.253762 11.00000 0.55643 0.14337 = 0.10465 0.00153 0.04379 0.05265 AFIX 137 H18A 2 0.038343 0.717335 1.242252 11.00000 -1.50000 H18B 2 0.119817 0.669221 1.297021 11.00000 -1.50000 H18C 2 -0.005140 0.636146 1.241868 11.00000 -1.50000 AFIX 0 C19 1 0.288750 0.584430 1.227595 11.00000 0.55643 0.14337 = 0.10465 0.00153 0.04379 0.05265 AFIX 137 H19A 2 0.206090 0.556385 1.201131 11.00000 -1.50000 H19B 2 0.285848 0.572255 1.269110 11.00000 -1.50000 H19C 2 0.401021 0.575226 1.218946 11.00000 -1.50000 AFIX 0 C20 1 -0.074587 0.827381 0.937363 11.00000 0.06310 0.06131 = 0.07155 0.00171 0.01428 -0.00319 C21 1 -0.230748 0.871537 0.930215 11.00000 0.06663 0.04821 = 0.05267 -0.00379 0.00842 0.00837 C22 1 -0.390261 0.843046 0.927945 11.00000 0.05787 0.04933 = 0.08696 -0.00360 0.02080 0.00234 AFIX 43 H22 2 -0.401516 0.794081 0.930764 11.00000 -1.20000 AFIX 0 C23 1 -0.533086 0.884383 0.921672 11.00000 0.08524 0.06261 = 0.09362 -0.00259 0.03759 0.01096 AFIX 43 H23 2 -0.641068 0.864825 0.920953 11.00000 -1.20000 AFIX 0 C24 1 -0.510095 0.957824 0.916338 11.00000 0.09112 0.06389 = 0.06768 0.00077 0.02063 0.01921 C25 1 -0.351275 0.987658 0.918974 11.00000 0.10480 0.04563 = 0.08036 0.00572 0.01476 0.01130 AFIX 43 H25 2 -0.338814 1.036614 0.916660 11.00000 -1.20000 AFIX 0 C26 1 -0.212554 0.944290 0.925032 11.00000 0.08393 0.04987 = 0.08101 -0.00354 0.01416 -0.01045 AFIX 43 H26 2 -0.104349 0.963611 0.925706 11.00000 -1.20000 AFIX 0 C27 1 0.304527 0.560662 0.856119 11.00000 0.03916 0.06871 = 0.06397 -0.00228 0.01410 0.00466 C28 1 0.261491 0.515459 0.806680 11.00000 0.06944 0.07190 = 0.07579 -0.00735 0.01365 -0.00860 AFIX 43 H28 2 0.217746 0.533663 0.768399 11.00000 -1.20000 AFIX 0 C29 1 0.283268 0.446469 0.814551 11.00000 0.08726 0.06456 = 0.08473 -0.01457 0.00757 -0.00473 AFIX 43 H29 2 0.247644 0.416271 0.781838 11.00000 -1.20000 AFIX 0 C30 1 0.356034 0.418071 0.868881 11.00000 0.08923 0.06961 = 0.10686 0.00355 0.04624 -0.00081 C31 1 0.401140 0.461097 0.917066 11.00000 0.08645 0.09883 = 0.08967 0.01394 0.01576 0.00645 AFIX 43 H31 2 0.448611 0.442024 0.954661 11.00000 -1.20000 AFIX 0 C32 1 0.376370 0.536006 0.910685 11.00000 0.05658 0.08668 = 0.06838 -0.00064 0.00797 -0.00685 AFIX 43 H32 2 0.409136 0.566514 0.943390 11.00000 -1.20000 AFIX 0 C33 1 0.387239 0.338041 0.878927 11.00000 0.55643 0.14337 = 0.10465 0.00153 0.04379 0.05265 AFIX 137 H33A 2 0.279297 0.313967 0.875518 11.00000 -1.50000 H33B 2 0.453241 0.330201 0.918708 11.00000 -1.50000 H33C 2 0.448657 0.319999 0.848825 11.00000 -1.50000 AFIX 0 BR2 3 0.007879 -0.019484 0.630964 11.00000 0.15299 0.08947 = 0.22523 0.03372 0.09802 -0.03314 SE2 6 0.421646 0.388121 0.582399 11.00000 0.05050 0.05682 = 0.12453 -0.03376 0.02826 -0.01077 S2 5 0.984579 0.351826 0.624785 11.00000 0.05273 0.05250 = 0.08775 0.01492 -0.01304 -0.00796 O5 4 0.511328 0.241293 0.553132 11.00000 0.06111 0.02895 = 0.06521 0.00301 0.01352 -0.00038 O6 4 0.710431 0.156749 0.569256 11.00000 0.06577 0.05246 = 0.17123 0.03085 0.02634 0.00832 O7 4 1.021826 0.312489 0.574945 11.00000 0.05222 0.05799 = 0.12066 -0.00583 0.00886 0.00352 O8 4 1.080131 0.336426 0.684502 11.00000 0.07805 0.09632 = 0.11741 0.03518 -0.03744 -0.02104 C34 1 0.484742 0.483404 0.602778 11.00000 0.04571 0.05185 = 0.05474 -0.01119 0.01451 -0.00254 C35 1 0.545534 0.528561 0.565051 11.00000 0.08387 0.06513 = 0.05722 -0.00501 0.01426 0.01079 AFIX 43 H35 2 0.563999 0.511753 0.527622 11.00000 -1.20000 AFIX 0 C36 1 0.581281 0.598140 0.579475 11.00000 0.09365 0.04591 = 0.08090 0.01130 0.01552 -0.00582 AFIX 43 H36 2 0.627733 0.627329 0.553022 11.00000 -1.20000 AFIX 0 C37 1 0.548612 0.623748 0.632137 11.00000 0.09813 0.05202 = 0.08570 -0.00099 0.02170 -0.00032 AFIX 43 H37 2 0.567985 0.671575 0.641123 11.00000 -1.20000 AFIX 0 C38 1 0.487562 0.581284 0.672906 11.00000 0.09175 0.07312 = 0.07081 -0.02758 0.01252 0.00899 AFIX 43 H38 2 0.465431 0.599183 0.709516 11.00000 -1.20000 AFIX 0 C39 1 0.459277 0.509045 0.657324 11.00000 0.07335 0.07234 = 0.06517 0.00041 0.01996 -0.00419 AFIX 43 H39 2 0.422452 0.478385 0.684977 11.00000 -1.20000 AFIX 0 C40 1 0.646530 0.354859 0.567744 11.00000 0.04343 0.03889 = 0.06554 -0.00055 0.01783 -0.00345 AFIX 13 H40 2 0.696532 0.392105 0.545750 11.00000 -1.20000 AFIX 0 C41 1 0.762659 0.343461 0.628293 11.00000 0.06078 0.05965 = 0.05450 0.00080 0.00876 -0.01973 AFIX 23 H41A 2 0.742034 0.296453 0.643170 11.00000 -1.20000 H41B 2 0.733611 0.377713 0.657242 11.00000 -1.20000 AFIX 0 C42 1 0.622082 0.288786 0.528012 11.00000 0.03910 0.03476 = 0.06704 0.01318 0.00962 0.00213 AFIX 13 H42 2 0.733608 0.265717 0.529849 11.00000 -1.20000 AFIX 0 C43 1 0.547087 0.302973 0.462390 11.00000 0.08402 0.02096 = 0.05266 0.00368 0.00835 0.00535 C44 1 0.657074 0.313073 0.421717 11.00000 0.09991 0.03326 = 0.08682 -0.00282 0.03311 -0.00281 AFIX 43 H44 2 0.775331 0.312523 0.434125 11.00000 -1.20000 AFIX 0 C45 1 0.580127 0.324472 0.359306 11.00000 0.24065 0.03008 = 0.06363 0.01668 0.06299 0.00119 AFIX 43 H45 2 0.654098 0.331462 0.331876 11.00000 -1.20000 AFIX 0 C46 1 0.417188 0.325952 0.337515 11.00000 0.18005 0.04087 = 0.06306 0.01128 0.00224 0.03067 C47 1 0.310698 0.316041 0.380573 11.00000 0.14297 0.05837 = 0.07409 -0.00175 -0.00607 0.03546 AFIX 43 H47 2 0.192721 0.317304 0.367510 11.00000 -1.20000 AFIX 0 C48 1 0.371758 0.304661 0.440561 11.00000 0.09049 0.06656 = 0.05591 0.00511 -0.00586 0.01752 AFIX 43 H48 2 0.295545 0.297944 0.467246 11.00000 -1.20000 AFIX 0 C49 1 0.357100 0.334937 0.272771 11.00000 0.27375 0.07254 = 0.08003 0.01661 -0.04041 0.07346 C50 1 0.392878 0.397829 0.248292 11.00000 0.49472 0.11840 = 0.07542 -0.00252 -0.06806 0.03543 AFIX 137 H50A 2 0.371824 0.435852 0.274602 11.00000 -1.50000 H50B 2 0.321205 0.403600 0.209227 11.00000 -1.50000 H50C 2 0.510934 0.398561 0.243717 11.00000 -1.50000 AFIX 0 C51 1 0.144139 0.343215 0.258132 11.00000 0.49472 0.11840 = 0.07542 -0.00252 -0.06806 0.03543 AFIX 137 H51A 2 0.092340 0.297880 0.262441 11.00000 -1.50000 H51B 2 0.108675 0.360213 0.217352 11.00000 -1.50000 H51C 2 0.108996 0.376309 0.286190 11.00000 -1.50000 AFIX 0 C52 1 0.370257 0.270418 0.237911 11.00000 0.49472 0.11840 = 0.07542 -0.00252 -0.06806 0.03543 AFIX 137 H52A 2 0.488758 0.259665 0.238341 11.00000 -1.50000 H52B 2 0.313127 0.277312 0.196732 11.00000 -1.50000 H52C 2 0.317552 0.231780 0.255699 11.00000 -1.50000 AFIX 0 C53 1 0.567409 0.175606 0.568458 11.00000 0.05142 0.03619 = 0.05694 -0.00503 0.00548 -0.00247 C54 1 0.431882 0.131471 0.587465 11.00000 0.07723 0.03165 = 0.04460 0.00272 0.00972 0.00117 C55 1 0.464846 0.059629 0.598456 11.00000 0.08267 0.04266 = 0.08264 0.00281 0.00698 -0.00431 AFIX 43 H55 2 0.572503 0.041364 0.596271 11.00000 -1.20000 AFIX 0 C56 1 0.340349 0.015758 0.612422 11.00000 0.11144 0.03421 = 0.08993 0.01562 0.02279 -0.00542 AFIX 43 H56 2 0.362573 -0.032252 0.619597 11.00000 -1.20000 AFIX 0 C57 1 0.183660 0.043005 0.615721 11.00000 0.11595 0.04895 = 0.09521 0.01122 0.04967 -0.01739 C58 1 0.145285 0.114026 0.606403 11.00000 0.08706 0.07259 = 0.11198 -0.00175 0.04580 -0.00241 AFIX 43 H58 2 0.038012 0.131768 0.609839 11.00000 -1.20000 AFIX 0 C59 1 0.271919 0.158032 0.591754 11.00000 0.07969 0.03456 = 0.08492 -0.00554 0.03977 -0.00749 AFIX 43 H59 2 0.249064 0.206021 0.584719 11.00000 -1.20000 AFIX 0 C60 1 1.006127 0.443907 0.611923 11.00000 0.03768 0.06576 = 0.07796 0.00055 -0.00951 -0.01089 C61 1 1.029084 0.465867 0.554486 11.00000 0.04686 0.07630 = 0.08325 0.01459 0.00901 -0.00313 AFIX 43 H61 2 1.031618 0.433235 0.523435 11.00000 -1.20000 AFIX 0 C62 1 1.048182 0.538362 0.544924 11.00000 0.07035 0.07065 = 0.10100 0.02949 -0.00576 -0.01135 AFIX 43 H62 2 1.068862 0.553633 0.507319 11.00000 -1.20000 AFIX 0 C63 1 1.037945 0.585931 0.587303 11.00000 0.07928 0.05419 = 0.11578 0.02556 -0.00661 -0.01543 C64 1 1.009467 0.563416 0.642136 11.00000 0.07458 0.05864 = 0.14524 -0.00682 -0.01091 0.00097 AFIX 43 H64 2 1.001261 0.597157 0.671858 11.00000 -1.20000 AFIX 0 C65 1 0.991590 0.490919 0.656364 11.00000 0.07152 0.07385 = 0.08322 -0.00960 0.00077 -0.02383 AFIX 43 H65 2 0.970984 0.476449 0.694195 11.00000 -1.20000 AFIX 0 C66 1 1.061937 0.664209 0.576125 11.00000 0.11696 0.05077 = 0.19822 0.02298 0.00396 -0.00047 AFIX 137 H66A 2 0.985516 0.691299 0.596037 11.00000 -1.50000 H66B 2 1.037443 0.673496 0.533227 11.00000 -1.50000 H66C 2 1.178073 0.677487 0.592019 11.00000 -1.50000 AFIX 0 HKLF 4 REM 180125_s4_wz_a.res in P2(1) REM R1 = 0.0676 for 6712 Fo > 4sig(Fo) and 0.1192 for all 10418 data REM 699 parameters refined using 3 restraints END WGHT 0.0584 5.9538 REM Instructions for potential hydrogen bonds HTAB C9 O4 EQIV $1 x-1, y, z HTAB C23 O2_$1 HTAB C42 O7 HTAB C58 O6_$1 REM Highest difference peak 0.578, deepest hole -0.493, 1-sigma level 0.066 Q1 1 0.4853 0.6070 1.2285 11.00000 0.05 0.44 Q2 1 0.5664 0.3607 0.2389 11.00000 0.05 0.44 Q3 1 -0.0793 0.6147 0.9267 11.00000 0.05 0.43 Q4 1 0.2458 0.3898 0.2597 11.00000 0.05 0.43 Q5 1 0.4612 0.4168 0.5483 11.00000 0.05 0.41 Q6 1 -0.1364 0.5953 0.9603 11.00000 0.05 0.41 Q7 1 -0.7181 0.9926 0.8551 11.00000 0.05 0.37 Q8 1 0.0846 0.0049 0.6751 11.00000 0.05 0.36 Q9 1 -0.0141 -0.0229 0.6174 11.00000 0.05 0.35 Q10 1 0.1282 0.5727 1.2178 11.00000 0.05 0.34 Q11 1 0.4028 0.3944 0.6497 11.00000 0.05 0.33 Q12 1 0.5031 0.3735 0.6230 11.00000 0.05 0.33 Q13 1 -0.1512 0.6470 0.9510 11.00000 0.05 0.33 Q14 1 0.4962 0.4311 0.6068 11.00000 0.05 0.32 Q15 1 0.1215 -0.0384 0.6841 11.00000 0.05 0.31 Q16 1 0.4382 0.3887 0.5175 11.00000 0.05 0.29 Q17 1 -0.1697 0.5621 0.9187 11.00000 0.05 0.29 Q18 1 -0.2200 0.5412 0.9697 11.00000 0.05 0.29 Q19 1 -0.2135 0.6177 0.8388 11.00000 0.05 0.27 Q20 1 0.2888 0.3846 0.5810 11.00000 0.05 0.26 ; _shelx_res_checksum 93131 _olex2_date_sample_data_collection 2018-01-25 _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 2.266 _oxdiff_exptl_absorpt_empirical_full_min 0.623 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 Br1 Br -0.7027(3) 1.01892(10) 0.90851(13) 0.1457(10) Uani 1 1 d . Se1 Se -0.22698(15) 0.61480(7) 0.91331(7) 0.0728(4) Uani 1 1 d . S1 S 0.2618(4) 0.65265(17) 0.84482(17) 0.0654(9) Uani 1 1 d . O1 O -0.0997(9) 0.7586(4) 0.9427(4) 0.062(2) Uani 1 1 d . O2 O 0.0668(13) 0.8519(6) 0.9418(8) 0.140(5) Uani 1 1 d . O3 O 0.2693(14) 0.6701(5) 0.7832(4) 0.096(3) Uani 1 1 d . O4 O 0.3643(11) 0.6914(5) 0.8931(5) 0.084(3) Uani 1 1 d . C1 C -0.1908(15) 0.5226(7) 0.8846(7) 0.068(4) Uani 1 1 d . C2 C -0.2525(18) 0.5038(9) 0.8261(7) 0.083(4) Uani 1 1 d . H2 H -0.3081 0.5377 0.7995 0.100 Uiso 1 1 calc R C3 C -0.235(3) 0.4352(13) 0.8051(11) 0.127(8) Uani 1 1 d . H3 H -0.2817 0.4234 0.7652 0.153 Uiso 1 1 calc R C4 C -0.150(3) 0.3863(14) 0.8421(16) 0.154(11) Uani 1 1 d . H4 H -0.1294 0.3415 0.8274 0.185 Uiso 1 1 calc R C5 C -0.093(3) 0.4031(12) 0.9025(13) 0.150(9) Uani 1 1 d . H5 H -0.0407 0.3685 0.9293 0.179 Uiso 1 1 calc R C6 C -0.113(2) 0.4700(8) 0.9227(8) 0.092(5) Uani 1 1 d . H6 H -0.0736 0.4806 0.9634 0.110 Uiso 1 1 calc R C7 C 0.0118(12) 0.6481(5) 0.9177(5) 0.045(3) Uani 1 1 d . H7 H 0.0882 0.6100 0.9359 0.054 Uiso 1 1 calc R C8 C 0.0429(14) 0.6595(6) 0.8521(5) 0.057(3) Uani 1 1 d . H8A H 0.0009 0.7062 0.8384 0.068 Uiso 1 1 calc R H8B H -0.0228 0.6246 0.8258 0.068 Uiso 1 1 calc R C9 C 0.0479(14) 0.7117(5) 0.9572(5) 0.052(3) Uani 1 1 d . H9 H 0.1465 0.7362 0.9458 0.063 Uiso 1 1 calc R C10 C 0.0877(18) 0.6983(6) 1.0237(6) 0.062(3) Uani 1 1 d . C11 C 0.255(2) 0.6946(7) 1.0512(7) 0.083(4) Uani 1 1 d . H11 H 0.3381 0.7012 1.0273 0.099 Uiso 1 1 calc R C12 C 0.308(3) 0.6816(8) 1.1119(9) 0.112(6) Uani 1 1 d . H12 H 0.4230 0.6806 1.1293 0.134 Uiso 1 1 calc R C13 C 0.179(5) 0.6699(9) 1.1466(8) 0.129(9) Uani 1 1 d . C14 C 0.013(4) 0.6745(11) 1.1201(12) 0.129(7) Uani 1 1 d . H14 H -0.0726 0.6677 1.1431 0.155 Uiso 1 1 calc R C15 C -0.030(3) 0.6891(9) 1.0591(9) 0.107(5) Uani 1 1 d . H15 H -0.1451 0.6927 1.0418 0.128 Uiso 1 1 calc R C16 C 0.251(6) 0.6536(11) 1.2186(10) 0.25(2) Uani 1 1 d . C17 C 0.370(4) 0.7168(14) 1.2477(12) 0.270(11) Uani 1 1 d D H17A H 0.4773 0.7148 1.2337 0.405 Uiso 1 1 calc GR H17B H 0.3892 0.7128 1.2912 0.405 Uiso 1 1 calc GR H17C H 0.3144 0.7612 1.2359 0.405 Uiso 1 1 calc GR C18 C 0.083(4) 0.6710(14) 1.2538(12) 0.270(11) Uani 1 1 d D H18A H 0.0383 0.7173 1.2423 0.405 Uiso 1 1 calc GR H18B H 0.1198 0.6692 1.2970 0.405 Uiso 1 1 calc GR H18C H -0.0051 0.6361 1.2419 0.405 Uiso 1 1 calc GR C19 C 0.289(5) 0.5844(14) 1.2276(12) 0.270(11) Uani 1 1 d D H19A H 0.2061 0.5564 1.2011 0.405 Uiso 1 1 calc GR H19B H 0.2858 0.5723 1.2691 0.405 Uiso 1 1 calc GR H19C H 0.4010 0.5752 1.2189 0.405 Uiso 1 1 calc GR C20 C -0.0746(16) 0.8274(7) 0.9374(6) 0.065(3) Uani 1 1 d . C21 C -0.2307(15) 0.8715(6) 0.9302(5) 0.056(3) Uani 1 1 d . C22 C -0.3903(15) 0.8430(7) 0.9279(6) 0.064(3) Uani 1 1 d . H22 H -0.4015 0.7941 0.9308 0.076 Uiso 1 1 calc R C23 C -0.5331(17) 0.8844(8) 0.9217(6) 0.078(4) Uani 1 1 d . H23 H -0.6411 0.8648 0.9210 0.093 Uiso 1 1 calc R C24 C -0.5101(19) 0.9578(8) 0.9163(6) 0.073(4) Uani 1 1 d . C25 C -0.351(2) 0.9877(7) 0.9190(6) 0.077(4) Uani 1 1 d . H25 H -0.3388 1.0366 0.9167 0.093 Uiso 1 1 calc R C26 C -0.2126(18) 0.9443(7) 0.9250(6) 0.072(4) Uani 1 1 d . H26 H -0.1043 0.9636 0.9257 0.086 Uiso 1 1 calc R C27 C 0.3045(14) 0.5607(6) 0.8561(6) 0.057(3) Uani 1 1 d . C28 C 0.2615(16) 0.5155(8) 0.8067(7) 0.072(4) Uani 1 1 d . H28 H 0.2177 0.5337 0.7684 0.087 Uiso 1 1 calc R C29 C 0.2833(18) 0.4465(8) 0.8146(8) 0.080(4) Uani 1 1 d . H29 H 0.2476 0.4163 0.7818 0.096 Uiso 1 1 calc R C30 C 0.356(2) 0.4181(8) 0.8689(9) 0.085(5) Uani 1 1 d . C31 C 0.4011(19) 0.4611(10) 0.9171(8) 0.092(5) Uani 1 1 d . H31 H 0.4486 0.4420 0.9547 0.110 Uiso 1 1 calc R C32 C 0.3764(16) 0.5360(8) 0.9107(7) 0.071(4) Uani 1 1 d . H32 H 0.4091 0.5665 0.9434 0.085 Uiso 1 1 calc R C33 C 0.387(6) 0.3380(14) 0.8789(12) 0.270(11) Uani 1 1 d . H33A H 0.2793 0.3140 0.8755 0.405 Uiso 1 1 calc GR H33B H 0.4532 0.3302 0.9187 0.405 Uiso 1 1 calc GR H33C H 0.4487 0.3200 0.8488 0.405 Uiso 1 1 calc GR Br2 Br 0.0079(3) -0.01948(10) 0.63096(13) 0.1480(10) Uani 1 1 d . Se2 Se 0.42165(14) 0.38812(7) 0.58240(7) 0.0757(5) Uani 1 1 d . S2 S 0.9846(4) 0.35183(17) 0.62478(18) 0.0674(10) Uani 1 1 d . O5 O 0.5113(9) 0.2413(3) 0.5531(3) 0.0515(18) Uani 1 1 d . O6 O 0.7104(12) 0.1567(5) 0.5693(6) 0.096(3) Uani 1 1 d . O7 O 1.0218(10) 0.3125(5) 0.5749(5) 0.078(3) Uani 1 1 d . O8 O 1.0801(12) 0.3364(5) 0.6845(5) 0.104(4) Uani 1 1 d . C34 C 0.4847(13) 0.4834(6) 0.6028(6) 0.050(3) Uani 1 1 d . C35 C 0.5455(17) 0.5286(7) 0.5651(6) 0.069(3) Uani 1 1 d . H35 H 0.5640 0.5118 0.5276 0.082 Uiso 1 1 calc R C36 C 0.5813(17) 0.5981(7) 0.5795(7) 0.073(4) Uani 1 1 d . H36 H 0.6277 0.6273 0.5530 0.088 Uiso 1 1 calc R C37 C 0.5486(17) 0.6237(7) 0.6321(7) 0.078(4) Uani 1 1 d . H37 H 0.5680 0.6716 0.6411 0.094 Uiso 1 1 calc R C38 C 0.4876(18) 0.5813(8) 0.6729(7) 0.079(4) Uani 1 1 d . H38 H 0.4654 0.5992 0.7095 0.095 Uiso 1 1 calc R C39 C 0.4593(16) 0.5090(7) 0.6573(6) 0.069(4) Uani 1 1 d . H39 H 0.4225 0.4784 0.6850 0.083 Uiso 1 1 calc R C40 C 0.6465(13) 0.3549(5) 0.5677(5) 0.048(3) Uani 1 1 d . H40 H 0.6965 0.3921 0.5457 0.058 Uiso 1 1 calc R C41 C 0.7627(14) 0.3435(6) 0.6283(5) 0.058(3) Uani 1 1 d . H41A H 0.7420 0.2965 0.6432 0.070 Uiso 1 1 calc R H41B H 0.7336 0.3777 0.6572 0.070 Uiso 1 1 calc R C42 C 0.6221(12) 0.2888(5) 0.5280(5) 0.047(3) Uani 1 1 d . H42 H 0.7336 0.2657 0.5298 0.056 Uiso 1 1 calc R C43 C 0.5471(17) 0.3030(5) 0.4624(6) 0.053(3) Uani 1 1 d . C44 C 0.657(2) 0.3131(6) 0.4217(7) 0.071(4) Uani 1 1 d . H44 H 0.7753 0.3125 0.4341 0.086 Uiso 1 1 calc R C45 C 0.580(4) 0.3245(7) 0.3593(8) 0.107(7) Uani 1 1 d . H45 H 0.6541 0.3315 0.3319 0.128 Uiso 1 1 calc R C46 C 0.417(3) 0.3260(8) 0.3375(8) 0.097(6) Uani 1 1 d . C47 C 0.311(3) 0.3160(7) 0.3806(8) 0.095(5) Uani 1 1 d . H47 H 0.1927 0.3173 0.3675 0.114 Uiso 1 1 calc R C48 C 0.3718(19) 0.3047(7) 0.4406(6) 0.073(4) Uani 1 1 d . H48 H 0.2955 0.2979 0.4672 0.088 Uiso 1 1 calc R C49 C 0.357(4) 0.3349(9) 0.2728(9) 0.151(10) Uani 1 1 d . C50 C 0.393(5) 0.3978(13) 0.2483(9) 0.244(12) Uani 1 1 d . H50A H 0.3718 0.4359 0.2746 0.366 Uiso 1 1 calc GR H50B H 0.3212 0.4036 0.2092 0.366 Uiso 1 1 calc GR H50C H 0.5109 0.3986 0.2437 0.366 Uiso 1 1 calc GR C51 C 0.144(5) 0.3432(13) 0.2581(10) 0.244(12) Uani 1 1 d . H51A H 0.0923 0.2979 0.2624 0.366 Uiso 1 1 calc GR H51B H 0.1087 0.3602 0.2174 0.366 Uiso 1 1 calc GR H51C H 0.1090 0.3763 0.2862 0.366 Uiso 1 1 calc GR C52 C 0.370(5) 0.2704(12) 0.2379(9) 0.244(12) Uani 1 1 d . H52A H 0.4888 0.2597 0.2383 0.366 Uiso 1 1 calc GR H52B H 0.3131 0.2773 0.1967 0.366 Uiso 1 1 calc GR H52C H 0.3176 0.2318 0.2557 0.366 Uiso 1 1 calc GR C53 C 0.5674(14) 0.1756(5) 0.5685(5) 0.049(3) Uani 1 1 d . C54 C 0.4319(15) 0.1315(5) 0.5875(5) 0.051(3) Uani 1 1 d . C55 C 0.4648(18) 0.0596(6) 0.5985(6) 0.070(4) Uani 1 1 d . H55 H 0.5725 0.0414 0.5963 0.084 Uiso 1 1 calc R C56 C 0.340(2) 0.0158(6) 0.6124(6) 0.078(4) Uani 1 1 d . H56 H 0.3626 -0.0323 0.6196 0.094 Uiso 1 1 calc R C57 C 0.184(2) 0.0430(7) 0.6157(7) 0.083(4) Uani 1 1 d . C58 C 0.1453(18) 0.1140(8) 0.6064(7) 0.087(4) Uani 1 1 d . H58 H 0.0380 0.1318 0.6098 0.105 Uiso 1 1 calc R C59 C 0.2719(16) 0.1580(6) 0.5918(6) 0.063(3) Uani 1 1 d . H59 H 0.2491 0.2060 0.5847 0.076 Uiso 1 1 calc R C60 C 1.0061(14) 0.4439(7) 0.6119(7) 0.063(3) Uani 1 1 d . C61 C 1.0291(14) 0.4659(7) 0.5545(7) 0.069(4) Uani 1 1 d . H61 H 1.0316 0.4332 0.5234 0.083 Uiso 1 1 calc R C62 C 1.0482(17) 0.5384(8) 0.5449(8) 0.083(4) Uani 1 1 d . H62 H 1.0689 0.5536 0.5073 0.100 Uiso 1 1 calc R C63 C 1.0379(19) 0.5859(8) 0.5873(10) 0.086(5) Uani 1 1 d . C64 C 1.0095(18) 0.5634(8) 0.6421(10) 0.097(5) Uani 1 1 d . H64 H 1.0013 0.5972 0.6719 0.116 Uiso 1 1 calc R C65 C 0.9916(16) 0.4909(7) 0.6564(7) 0.078(4) Uani 1 1 d . H65 H 0.9710 0.4764 0.6942 0.093 Uiso 1 1 calc R C66 C 1.062(2) 0.6642(8) 0.5761(10) 0.125(7) Uani 1 1 d . H66A H 0.9855 0.6913 0.5960 0.187 Uiso 1 1 calc GR H66B H 1.0374 0.6735 0.5332 0.187 Uiso 1 1 calc GR H66C H 1.1781 0.6775 0.5920 0.187 Uiso 1 1 calc GR 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 0.1220(15) 0.0952(14) 0.236(3) 0.0420(15) 0.0750(17) 0.0530(12) Se1 0.0527(7) 0.0668(8) 0.1041(11) -0.0152(8) 0.0280(7) -0.0056(6) S1 0.0661(19) 0.062(2) 0.075(2) -0.0025(18) 0.0322(18) -0.0054(15) O1 0.056(4) 0.041(4) 0.092(6) 0.003(4) 0.021(4) 0.000(4) O2 0.065(6) 0.075(7) 0.288(17) 0.053(9) 0.050(8) 0.000(5) O3 0.137(9) 0.081(6) 0.087(7) 0.018(6) 0.069(6) 0.010(6) O4 0.062(5) 0.073(6) 0.120(8) -0.034(6) 0.029(5) -0.016(4) C1 0.059(8) 0.072(9) 0.076(10) -0.034(8) 0.024(7) -0.016(7) C2 0.075(9) 0.100(12) 0.076(11) -0.023(9) 0.015(8) -0.009(8) C3 0.118(17) 0.137(19) 0.130(19) -0.074(16) 0.033(14) -0.041(14) C4 0.123(18) 0.097(17) 0.25(4) -0.07(2) 0.06(2) -0.017(14) C5 0.21(3) 0.085(16) 0.15(2) 0.018(14) 0.018(19) 0.004(15) C6 0.102(12) 0.065(10) 0.105(13) -0.001(9) 0.010(10) 0.001(8) C7 0.038(5) 0.037(5) 0.060(8) -0.006(5) 0.009(5) -0.002(4) C8 0.059(7) 0.058(7) 0.053(7) 0.008(6) 0.007(6) 0.006(5) C9 0.057(7) 0.043(6) 0.059(8) 0.009(6) 0.018(6) 0.001(5) C10 0.082(9) 0.045(6) 0.058(9) 0.003(6) 0.014(8) 0.002(6) C11 0.130(14) 0.051(8) 0.062(11) -0.005(7) 0.001(9) -0.003(8) C12 0.170(19) 0.073(11) 0.077(14) 0.000(10) -0.025(13) 0.001(11) C13 0.29(3) 0.042(8) 0.052(12) 0.004(8) 0.034(17) -0.009(15) C14 0.19(2) 0.118(17) 0.097(19) -0.002(14) 0.061(16) -0.002(17) C15 0.139(16) 0.105(14) 0.082(14) -0.004(10) 0.035(12) -0.001(11) C16 0.61(6) 0.073(14) 0.073(15) -0.019(11) 0.06(2) 0.08(2) C17 0.56(4) 0.143(13) 0.105(11) 0.002(9) 0.044(15) 0.053(16) C18 0.56(4) 0.143(13) 0.105(11) 0.002(9) 0.044(15) 0.053(16) C19 0.56(4) 0.143(13) 0.105(11) 0.002(9) 0.044(15) 0.053(16) C20 0.063(8) 0.061(8) 0.072(9) 0.002(7) 0.014(7) -0.003(6) C21 0.067(8) 0.048(7) 0.053(7) -0.004(5) 0.008(6) 0.008(5) C22 0.058(7) 0.049(7) 0.087(10) -0.004(7) 0.021(7) 0.002(6) C23 0.085(9) 0.063(9) 0.094(11) -0.003(8) 0.038(8) 0.011(8) C24 0.091(10) 0.064(9) 0.068(10) 0.001(7) 0.021(8) 0.019(8) C25 0.105(11) 0.046(7) 0.080(10) 0.006(7) 0.015(9) 0.011(8) C26 0.084(10) 0.050(8) 0.081(10) -0.004(7) 0.014(8) -0.010(7) C27 0.039(6) 0.069(8) 0.064(9) -0.002(7) 0.014(6) 0.005(6) C28 0.069(8) 0.072(9) 0.076(10) -0.007(8) 0.014(7) -0.009(7) C29 0.087(10) 0.065(9) 0.085(12) -0.015(8) 0.008(8) -0.005(8) C30 0.089(11) 0.070(10) 0.107(14) 0.004(10) 0.046(10) -0.001(8) C31 0.086(11) 0.099(13) 0.090(13) 0.014(11) 0.016(9) 0.006(9) C32 0.057(8) 0.087(10) 0.068(10) -0.001(8) 0.008(7) -0.007(7) C33 0.56(4) 0.143(13) 0.105(11) 0.002(9) 0.044(15) 0.053(16) Br2 0.1530(18) 0.0895(13) 0.225(3) 0.0337(15) 0.0980(18) -0.0331(12) Se2 0.0505(7) 0.0568(7) 0.1245(13) -0.0338(8) 0.0283(7) -0.0108(6) S2 0.0527(18) 0.0525(18) 0.088(3) 0.0149(18) -0.0130(18) -0.0080(14) O5 0.061(4) 0.029(4) 0.065(5) 0.003(3) 0.014(4) 0.000(3) O6 0.066(6) 0.052(5) 0.171(11) 0.031(6) 0.026(6) 0.008(4) O7 0.052(5) 0.058(5) 0.121(8) -0.006(5) 0.009(5) 0.004(4) O8 0.078(6) 0.096(7) 0.117(9) 0.035(6) -0.037(6) -0.021(5) C34 0.046(6) 0.052(7) 0.055(8) -0.011(6) 0.015(6) -0.003(5) C35 0.084(9) 0.065(8) 0.057(9) -0.005(7) 0.014(7) 0.011(7) C36 0.094(10) 0.046(8) 0.081(11) 0.011(7) 0.016(8) -0.006(6) C37 0.098(10) 0.052(8) 0.086(11) -0.001(8) 0.022(8) 0.000(7) C38 0.092(10) 0.073(9) 0.071(10) -0.028(8) 0.013(8) 0.009(8) C39 0.073(8) 0.072(9) 0.065(9) 0.000(7) 0.020(7) -0.004(7) C40 0.043(6) 0.039(6) 0.066(8) -0.001(5) 0.018(6) -0.003(4) C41 0.061(7) 0.060(7) 0.054(8) 0.001(6) 0.009(6) -0.020(6) C42 0.039(5) 0.035(5) 0.067(8) 0.013(5) 0.010(5) 0.002(4) C43 0.084(9) 0.021(5) 0.053(8) 0.004(5) 0.008(7) 0.005(5) C44 0.100(10) 0.033(6) 0.087(12) -0.003(7) 0.033(9) -0.003(6) C45 0.24(3) 0.030(7) 0.064(13) 0.017(7) 0.063(14) 0.001(11) C46 0.18(2) 0.041(8) 0.063(13) 0.011(7) 0.002(13) 0.031(11) C47 0.143(15) 0.058(9) 0.074(13) -0.002(8) -0.006(12) 0.035(9) C48 0.090(10) 0.067(8) 0.056(10) 0.005(7) -0.006(8) 0.018(7) C49 0.27(3) 0.073(12) 0.080(14) 0.017(9) -0.040(15) 0.073(15) C50 0.49(4) 0.118(12) 0.075(9) -0.003(8) -0.068(14) 0.035(14) C51 0.49(4) 0.118(12) 0.075(9) -0.003(8) -0.068(14) 0.035(14) C52 0.49(4) 0.118(12) 0.075(9) -0.003(8) -0.068(14) 0.035(14) C53 0.051(7) 0.036(6) 0.057(8) -0.005(5) 0.005(6) -0.002(5) C54 0.077(8) 0.032(6) 0.045(7) 0.003(5) 0.010(6) 0.001(5) C55 0.083(9) 0.043(7) 0.083(10) 0.003(6) 0.007(8) -0.004(6) C56 0.111(12) 0.034(7) 0.090(11) 0.016(7) 0.023(9) -0.005(7) C57 0.116(12) 0.049(8) 0.095(12) 0.011(7) 0.050(10) -0.017(8) C58 0.087(9) 0.073(9) 0.112(12) -0.002(9) 0.046(8) -0.002(8) C59 0.080(8) 0.035(6) 0.085(10) -0.006(6) 0.040(7) -0.007(6) C60 0.038(6) 0.066(8) 0.078(10) 0.001(8) -0.010(6) -0.011(6) C61 0.047(7) 0.076(9) 0.083(11) 0.015(8) 0.009(7) -0.003(6) C62 0.070(9) 0.071(10) 0.101(13) 0.029(9) -0.006(8) -0.011(7) C63 0.079(10) 0.054(9) 0.116(15) 0.026(9) -0.007(10) -0.015(7) C64 0.075(10) 0.059(9) 0.145(17) -0.007(10) -0.011(10) 0.001(7) C65 0.072(9) 0.074(10) 0.083(11) -0.010(8) 0.001(8) -0.024(7) C66 0.117(13) 0.051(9) 0.20(2) 0.023(11) 0.004(13) 0.000(9) 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' Se Se -0.0929 2.2259 '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 C1 Se1 C7 96.1(5) O3 S1 O4 119.7(7) O3 S1 C8 106.3(6) O3 S1 C27 108.8(6) O4 S1 C8 109.1(6) O4 S1 C27 108.8(6) C27 S1 C8 102.9(5) C20 O1 C9 119.2(9) C2 C1 Se1 121.0(12) C2 C1 C6 116.9(14) C6 C1 Se1 121.9(11) C1 C2 C3 121.8(17) C4 C3 C2 120(2) C3 C4 C5 119(2) C6 C5 C4 120(2) C5 C6 C1 121.8(18) C8 C7 Se1 108.0(7) C9 C7 Se1 111.5(7) C9 C7 C8 113.9(9) C7 C8 S1 113.6(8) O1 C9 C7 107.1(9) O1 C9 C10 110.2(9) C10 C9 C7 116.2(9) C11 C10 C9 118.6(13) C15 C10 C9 124.6(15) C15 C10 C11 116.9(16) C10 C11 C12 124.0(17) C11 C12 C13 117(2) C12 C13 C16 114(3) C14 C13 C12 119.7(19) C14 C13 C16 126(3) C13 C14 C15 120(2) C10 C15 C14 122.5(19) C13 C16 C18 105(3) C17 C16 C13 110(2) C17 C16 C18 97.1(14) C19 C16 C13 110.9(19) C19 C16 C17 125(4) C19 C16 C18 107(3) O1 C20 C21 115.2(11) O2 C20 O1 121.6(12) O2 C20 C21 123.0(12) C22 C21 C20 122.4(11) C22 C21 C26 119.7(11) C26 C21 C20 117.9(12) C23 C22 C21 121.8(12) C22 C23 C24 117.0(13) C23 C24 Br1 119.5(11) C25 C24 Br1 118.3(11) C25 C24 C23 122.2(13) C26 C25 C24 118.7(13) C25 C26 C21 120.6(13) C28 C27 S1 118.1(11) C32 C27 S1 120.6(11) C32 C27 C28 121.2(13) C29 C28 C27 119.4(14) C28 C29 C30 122.2(15) C29 C30 C33 123.3(19) C31 C30 C29 119.3(15) C31 C30 C33 117.4(19) C30 C31 C32 120.2(15) C27 C32 C31 117.6(14) C34 Se2 C40 97.6(4) O7 S2 O8 118.4(6) O7 S2 C41 109.5(6) O7 S2 C60 110.3(7) O8 S2 C41 107.6(6) O8 S2 C60 107.3(6) C60 S2 C41 102.6(6) C53 O5 C42 118.5(8) C35 C34 Se2 123.8(10) C35 C34 C39 117.6(12) C39 C34 Se2 118.5(9) C34 C35 C36 122.7(13) C37 C36 C35 119.2(14) C36 C37 C38 121.5(13) C37 C38 C39 117.4(13) C34 C39 C38 121.4(13) C41 C40 Se2 108.8(8) C41 C40 C42 113.6(9) C42 C40 Se2 109.4(6) C40 C41 S2 113.5(8) O5 C42 C40 107.8(9) O5 C42 C43 109.1(8) C43 C42 C40 114.3(8) C44 C43 C42 118.6(12) C44 C43 C48 118.4(13) C48 C43 C42 123.0(12) C43 C44 C45 116.8(15) C46 C45 C44 126.2(19) C45 C46 C47 114.9(17) C45 C46 C49 120(2) C47 C46 C49 125(2) C48 C47 C46 123.1(17) C47 C48 C43 120.6(15) C46 C49 C51 110(2) C46 C49 C52 113.2(14) C50 C49 C46 117(2) C50 C49 C51 96.7(18) C50 C49 C52 118(2) C52 C49 C51 98(2) O5 C53 C54 111.6(9) O6 C53 O5 123.7(10) O6 C53 C54 124.7(10) C55 C54 C53 118.3(11) C59 C54 C53 122.6(10) C59 C54 C55 119.0(11) C56 C55 C54 120.5(13) C57 C56 C55 119.3(12) C56 C57 Br2 118.9(10) C56 C57 C58 122.5(12) C58 C57 Br2 118.6(12) C57 C58 C59 117.8(13) C54 C59 C58 120.8(12) C61 C60 S2 118.2(11) C65 C60 S2 120.0(12) C65 C60 C61 121.7(13) C60 C61 C62 117.9(14) C63 C62 C61 122.3(16) C62 C63 C64 118.7(14) C62 C63 C66 121.3(18) C64 C63 C66 120.1(18) C63 C64 C65 123.1(17) C60 C65 C64 116.3(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C24 1.896(13) Se1 C1 1.892(13) Se1 C7 1.981(10) S1 O3 1.428(10) S1 O4 1.431(10) S1 C8 1.778(11) S1 C27 1.775(13) O1 C9 1.457(12) O1 C20 1.320(14) O2 C20 1.201(15) C1 C2 1.359(18) C1 C6 1.379(19) C2 C3 1.39(2) C3 C4 1.34(3) C4 C5 1.38(3) C5 C6 1.36(3) C7 C8 1.543(15) C7 C9 1.486(14) C9 C10 1.486(17) C10 C11 1.359(19) C10 C15 1.34(2) C11 C12 1.37(2) C12 C13 1.40(3) C13 C14 1.35(3) C13 C16 1.64(3) C14 C15 1.37(3) C16 C17 1.58(4) C16 C18 1.70(5) C16 C19 1.34(3) C20 C21 1.477(16) C21 C22 1.367(16) C21 C26 1.385(17) C22 C23 1.361(17) C23 C24 1.40(2) C24 C25 1.371(19) C25 C26 1.358(18) C27 C28 1.389(17) C27 C32 1.335(17) C28 C29 1.319(18) C29 C30 1.36(2) C30 C31 1.34(2) C30 C33 1.54(3) C31 C32 1.43(2) Br2 C57 1.901(13) Se2 C34 1.897(11) Se2 C40 1.972(10) S2 O7 1.412(10) S2 O8 1.443(10) S2 C41 1.783(11) S2 C60 1.772(13) O5 C42 1.436(11) O5 C53 1.339(12) O6 C53 1.186(12) C34 C35 1.346(16) C34 C39 1.359(16) C35 C36 1.368(17) C36 C37 1.339(18) C37 C38 1.364(19) C38 C39 1.413(18) C40 C41 1.512(15) C40 C42 1.521(14) C42 C43 1.506(16) C43 C44 1.380(18) C43 C48 1.390(17) C44 C45 1.44(2) C45 C46 1.30(3) C46 C47 1.40(2) C46 C49 1.45(2) C47 C48 1.36(2) C49 C50 1.36(3) C49 C51 1.67(4) C49 C52 1.46(3) C53 C54 1.480(15) C54 C55 1.392(15) C54 C59 1.383(15) C55 C56 1.366(17) C56 C57 1.359(19) C57 C58 1.38(2) C58 C59 1.386(17) C60 C61 1.391(18) C60 C65 1.351(18) C61 C62 1.395(19) C62 C63 1.32(2) C63 C64 1.35(2) C63 C66 1.513(19) C64 C65 1.42(2) 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 Br1 C24 C25 C26 179.5(10) Se1 C1 C2 C3 -176.7(13) Se1 C1 C6 C5 177.6(16) Se1 C7 C8 S1 -154.9(6) Se1 C7 C9 O1 -43.0(10) Se1 C7 C9 C10 80.7(11) S1 C27 C28 C29 -176.4(11) S1 C27 C32 C31 177.7(10) O1 C9 C10 C11 -141.7(10) O1 C9 C10 C15 38.6(16) O1 C20 C21 C22 -1.4(18) O1 C20 C21 C26 179.3(12) O2 C20 C21 C22 -177.0(15) O2 C20 C21 C26 4(2) O3 S1 C8 C7 -175.5(8) O3 S1 C27 C28 -28.7(11) O3 S1 C27 C32 151.2(10) O4 S1 C8 C7 -45.2(10) O4 S1 C27 C28 -160.6(9) O4 S1 C27 C32 19.2(12) C1 C2 C3 C4 -2(3) C2 C1 C6 C5 2(2) C2 C3 C4 C5 5(4) C3 C4 C5 C6 -4(4) C4 C5 C6 C1 0(3) C6 C1 C2 C3 -2(2) C7 Se1 C1 C2 -107.3(11) C7 Se1 C1 C6 77.8(12) C7 C9 C10 C11 96.3(13) C7 C9 C10 C15 -83.4(16) C8 S1 C27 C28 83.7(10) C8 S1 C27 C32 -96.4(10) C8 C7 C9 O1 79.6(10) C8 C7 C9 C10 -156.7(10) C9 O1 C20 O2 3(2) C9 O1 C20 C21 -172.7(10) C9 C7 C8 S1 80.5(10) C9 C10 C11 C12 -179.2(13) C9 C10 C15 C14 177.8(16) C10 C11 C12 C13 2(2) C11 C10 C15 C14 -2(2) C11 C12 C13 C14 -3(3) C11 C12 C13 C16 179.2(13) C12 C13 C14 C15 1(3) C12 C13 C16 C17 57(3) C12 C13 C16 C18 160.2(18) C12 C13 C16 C19 -85(4) C13 C14 C15 C10 1(3) C14 C13 C16 C17 -121(3) C14 C13 C16 C18 -18(3) C14 C13 C16 C19 97(4) C15 C10 C11 C12 1(2) C16 C13 C14 C15 179.4(17) C20 O1 C9 C7 -137.0(10) C20 O1 C9 C10 95.7(12) C20 C21 C22 C23 179.6(12) C20 C21 C26 C25 -179.3(12) C21 C22 C23 C24 1.3(19) C22 C21 C26 C25 1(2) C22 C23 C24 Br1 -179.2(10) C22 C23 C24 C25 -2(2) C23 C24 C25 C26 2(2) C24 C25 C26 C21 -2(2) C26 C21 C22 C23 -1.1(19) C27 S1 C8 C7 70.3(9) C27 C28 C29 C30 -4(2) C28 C27 C32 C31 -2.5(18) C28 C29 C30 C31 3(2) C28 C29 C30 C33 -178(2) C29 C30 C31 C32 -1(2) C30 C31 C32 C27 1(2) C32 C27 C28 C29 3.8(19) C33 C30 C31 C32 180(2) Br2 C57 C58 C59 -176.2(11) Se2 C34 C35 C36 176.3(10) Se2 C34 C39 C38 -173.7(10) Se2 C40 C41 S2 -153.9(6) Se2 C40 C42 O5 -47.9(9) Se2 C40 C42 C43 73.5(10) S2 C60 C61 C62 -179.2(9) S2 C60 C65 C64 -179.6(9) O5 C42 C43 C44 -146.1(9) O5 C42 C43 C48 32.3(13) O5 C53 C54 C55 173.2(11) O5 C53 C54 C59 -3.6(15) O6 C53 C54 C55 -10.2(19) O6 C53 C54 C59 173.1(13) O7 S2 C41 C40 -47.4(10) O7 S2 C60 C61 9.3(11) O7 S2 C60 C65 -174.0(10) O8 S2 C41 C40 -177.3(8) O8 S2 C60 C61 139.5(10) O8 S2 C60 C65 -43.8(12) C34 C35 C36 C37 -3(2) C35 C34 C39 C38 3.0(19) C35 C36 C37 C38 3(2) C36 C37 C38 C39 0(2) C37 C38 C39 C34 -3(2) C39 C34 C35 C36 -0.2(19) C40 Se2 C34 C35 60.0(11) C40 Se2 C34 C39 -123.5(10) C40 C42 C43 C44 93.2(11) C40 C42 C43 C48 -88.4(12) C41 S2 C60 C61 -107.3(10) C41 S2 C60 C65 69.4(11) C41 C40 C42 O5 73.8(10) C41 C40 C42 C43 -164.7(9) C42 O5 C53 O6 9.2(17) C42 O5 C53 C54 -174.1(9) C42 C40 C41 S2 84.0(10) C42 C43 C44 C45 178.3(9) C42 C43 C48 C47 -178.4(11) C43 C44 C45 C46 0(2) C44 C43 C48 C47 0.0(17) C44 C45 C46 C47 1(2) C44 C45 C46 C49 -177.3(13) C45 C46 C47 C48 -1(2) C45 C46 C49 C50 -65(3) C45 C46 C49 C51 -174.2(16) C45 C46 C49 C52 77(3) C46 C47 C48 C43 1(2) C47 C46 C49 C50 117(3) C47 C46 C49 C51 8(2) C47 C46 C49 C52 -101(3) C48 C43 C44 C45 -0.2(15) C49 C46 C47 C48 177.0(14) C53 O5 C42 C40 -123.3(9) C53 O5 C42 C43 112.1(10) C53 C54 C55 C56 -175.9(12) C53 C54 C59 C58 176.3(12) C54 C55 C56 C57 0(2) C55 C54 C59 C58 -0.4(19) C55 C56 C57 Br2 176.7(11) C55 C56 C57 C58 -1(2) C56 C57 C58 C59 2(2) C57 C58 C59 C54 -1(2) C59 C54 C55 C56 0.9(19) C60 S2 C41 C40 69.7(10) C60 C61 C62 C63 -3(2) C61 C60 C65 C64 -3.0(18) C61 C62 C63 C64 1(2) C61 C62 C63 C66 179.0(13) C62 C63 C64 C65 1(2) C63 C64 C65 C60 1(2) C65 C60 C61 C62 4.2(17) C66 C63 C64 C65 -177.8(14)