#------------------------------------------------------------------------------ #$Date: 2017-11-21 10:50:44 +0200 (Tue, 21 Nov 2017) $ #$Revision: 203412 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/88/7228838.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_7228838 loop_ _publ_author_name 'Lopez, Jordan R.' 'Martin, Lee' 'Wallis, John D.' 'Akutsu, Hiroki' 'Yamada, Jun-ichi' 'Nakatsuji, Shin-ichi' 'Wilson, Claire' 'Christensen, Jeppe' 'Coles, Simon J.' _publ_section_title ; New semiconducting radical-cation salts of chiral bis(2-hydroxylpropylthio)ethylenedithio TTF ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE01014A _journal_year 2017 _chemical_absolute_configuration syn _chemical_formula_sum 'C14 H18 Br O2 S8' _chemical_formula_weight 554.67 _chemical_name_systematic ; (S,S)-Bis(2-hydroxypropylthio)(ethylenedithio) tetrathiafulvalene) bromide ; _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 mixed _audit_creation_method SHELXL-2014 _audit_update_record ; 2017-05-10 deposited with the CCDC. 2017-07-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.857(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.8310(2) _cell_length_b 19.9437(4) _cell_length_c 10.6022(2) _cell_measurement_reflns_used 4596 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29 _cell_measurement_theta_min 3 _cell_volume 2059.22(7) _computing_cell_refinement 'CrysAlisPro, (Agilent, 2011)' _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlisPro, (Agilent, 2011)' _computing_structure_refinement ; CRYSTALS(Betteridge et al.,2003),SHELXL-2014(Sheldrick, 2014) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.854 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_unetI/netI 0.0452 _diffrn_reflns_Laue_measured_fraction_full 0.980 _diffrn_reflns_Laue_measured_fraction_max 0.854 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 10669 _diffrn_reflns_point_group_measured_fraction_full 0.774 _diffrn_reflns_point_group_measured_fraction_max 0.662 _diffrn_reflns_theta_full 27.000 _diffrn_reflns_theta_max 29.029 _diffrn_reflns_theta_min 2.924 _exptl_absorpt_coefficient_mu 2.815 _exptl_absorpt_correction_T_max 0.84 _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_crystal_colour black _exptl_crystal_density_diffrn 1.789 _exptl_crystal_description plate _exptl_crystal_F_000 1124 _exptl_crystal_size_max 0.372 _exptl_crystal_size_mid 0.082 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.832 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.086 _refine_ls_abs_structure_details ; Flack x determined using 2202 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.002(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 471 _refine_ls_number_reflns 7282 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0342 _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^)+(0.0329P)^2^+0.5662P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.0759 _reflns_Friedel_coverage 0.509 _reflns_Friedel_fraction_full 0.556 _reflns_Friedel_fraction_max 0.459 _reflns_number_gt 6862 _reflns_number_total 7282 _reflns_threshold_expression 'I > 2\s(I)' _cod_depositor_comments ; 2017-11-03 Z value and formula fixed to values more according to usual chemical conventions. miguel ; _cod_original_formula_sum 'C28 H36 Br2 O4 S16' _cod_original_formula_weight 1109.35 _cod_original_formula_units_Z 2 _cod_data_source_file c7ce01014a2.cif _cod_data_source_block 6 _cod_database_code 7228838 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2014-3 _shelx_res_file ; REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0345 for 6862 Fo > 4sig(Fo) and 0.0378 for all 7282 data REM 467 parameters refined using 1 restraints REM Highest difference peak 0.894, deepest hole -0.393, 1-sigma level 0.087 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0343 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 1 restraints REM Highest difference peak 0.889, deepest hole -0.393, 1-sigma level 0.087 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0341 for 6862 Fo > 4sig(Fo) and 0.0374 for all 7282 data REM 471 parameters refined using 1 restraints REM Highest difference peak 0.857, deepest hole -0.450, 1-sigma level 0.086 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0341 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 1 restraints REM Highest difference peak 0.842, deepest hole -0.483, 1-sigma level 0.086 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0342 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 1 restraints REM Highest difference peak 0.837, deepest hole -0.491, 1-sigma level 0.086 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0342 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 5 restraints REM Highest difference peak 0.834, deepest hole -0.496, 1-sigma level 0.086 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0342 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 5 restraints REM Highest difference peak 0.833, deepest hole -0.496, 1-sigma level 0.086 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0342 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 6 restraints REM Highest difference peak 0.829, deepest hole -0.488, 1-sigma level 0.086 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0342 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 6 restraints REM Highest difference peak 0.830, deepest hole -0.487, 1-sigma level 0.086 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0342 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 6 restraints REM Highest difference peak 0.831, deepest hole -0.483, 1-sigma level 0.086 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0342 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 6 restraints REM Highest difference peak 0.832, deepest hole -0.483, 1-sigma level 0.086 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0342 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 6 restraints REM Highest difference peak 0.831, deepest hole -0.484, 1-sigma level 0.086 TITL ssbr3_Gabsnew in P2(1) CELL 0.71073 9.8310 19.9437 10.6022 90.000 97.857 90.000 ZERR 2.0000 0.0002 0.0004 0.0002 0.000 0.002 0.000 LATT -1 SYMM -X, 0.5+Y, -Z SFAC C H O S BR UNIT 56 72 8 32 4 MERG 2 FMAP 2 GRID PLAN 20 TEMP -123 CONF DFIX 0.85 0.001 O1 H1 O2 H2 O3 H3 O4 H4 DFIX 2.10 0.001 H1 H10 EQIV $1 -x-1, y+1/2, -z-1 EQIV $2 x+1, y, z+1 EQIV $3 x-1, y, z-1 EQIV $4 -x-1, y-1/2, -z-2 HTAB O1 Br1_$1 HTAB O2 Br2_$2 HTAB O3 Br1_$3 HTAB O4 Br2_$4 L.S. 6 ACTA 54 WGHT 0.032900 0.566200 FVAR 2.91343 BR1 5 -0.193344 -0.849762 -0.507172 11.00000 0.02548 0.02911 = 0.02080 0.00316 -0.00179 0.00134 BR2 5 -0.795954 -0.572040 -1.014666 11.00000 0.02595 0.02839 = 0.02893 0.00450 0.00033 0.00320 S1 4 -1.024642 -0.831332 -0.879978 11.00000 0.01712 0.01999 = 0.02631 0.00166 -0.00314 -0.00220 S2 4 -0.828400 -0.930107 -0.646398 11.00000 0.02686 0.01721 = 0.03267 0.00863 -0.00210 -0.00420 S3 4 -0.811229 -0.729238 -0.804396 11.00000 0.01615 0.01421 = 0.02038 0.00136 -0.00156 0.00092 S4 4 -0.646869 -0.814906 -0.618994 11.00000 0.01920 0.01640 = 0.01767 0.00202 -0.00186 0.00096 S5 4 -0.587806 -0.605910 -0.713517 11.00000 0.01517 0.01744 = 0.01932 0.00274 -0.00158 0.00008 S6 4 -0.443027 -0.700948 -0.531981 11.00000 0.02108 0.01696 = 0.02093 0.00222 -0.00393 -0.00199 S7 4 -0.396007 -0.491904 -0.618113 11.00000 0.02591 0.01912 = 0.03091 0.00542 -0.00747 -0.00439 S8 4 -0.231103 -0.599774 -0.426833 11.00000 0.01909 0.01940 = 0.01846 0.00281 -0.00307 -0.00316 S9 4 -0.141287 -0.490950 -0.851781 11.00000 0.02738 0.01701 = 0.02860 0.00670 0.00221 -0.00316 S10 4 0.051583 -0.594298 -0.623389 11.00000 0.01796 0.01852 = 0.02836 -0.00044 -0.00157 -0.00396 S11 4 -0.316995 -0.608310 -0.898050 11.00000 0.02007 0.01608 = 0.01926 0.00202 -0.00054 0.00021 S12 4 -0.159490 -0.694973 -0.710960 11.00000 0.01609 0.01332 = 0.02146 0.00061 -0.00063 -0.00039 S13 4 -0.527714 -0.723076 -0.983452 11.00000 0.02089 0.01526 = 0.02026 0.00294 -0.00326 -0.00163 S14 4 -0.378930 -0.815856 -0.801493 11.00000 0.01559 0.01471 = 0.02136 0.00202 -0.00173 -0.00038 S15 4 -0.738535 -0.825918 -1.083213 11.00000 0.01844 0.01883 = 0.01931 0.00222 -0.00243 -0.00350 S16 4 -0.567390 -0.931293 -0.884580 11.00000 0.01850 0.01480 = 0.02478 0.00218 -0.00278 -0.00232 O1 3 -0.548181 -0.359935 -0.653214 11.00000 0.03016 0.02505 = 0.03841 -0.01228 0.00060 -0.00341 O2 3 -0.123997 -0.582175 -0.146129 11.00000 0.03112 0.01963 = 0.02965 -0.00084 -0.00693 -0.00180 O3 3 -0.960344 -0.808518 -1.278333 11.00000 0.02531 0.04453 = 0.02105 0.00280 -0.00230 -0.01137 O4 3 -0.481146 -1.077777 -0.840716 11.00000 0.02667 0.02083 = 0.03610 -0.00486 0.00275 -0.00662 C1 1 -1.012221 -0.921736 -0.866110 11.00000 0.03000 0.02024 = 0.02794 -0.00632 -0.00307 -0.00630 AFIX 23 H1B 2 -1.095447 -0.942038 -0.914297 11.00000 -1.20000 H1A 2 -0.932091 -0.937146 -0.905566 11.00000 -1.20000 AFIX 0 C2 1 -0.997651 -0.946171 -0.731884 11.00000 0.02317 0.02052 = 0.02866 -0.00041 0.00236 -0.00596 AFIX 23 H2B 2 -1.015843 -0.994994 -0.731868 11.00000 -1.20000 H2A 2 -1.067167 -0.923803 -0.687109 11.00000 -1.20000 AFIX 0 C3 1 -0.873738 -0.809745 -0.782867 11.00000 0.01493 0.01815 = 0.01668 -0.00110 0.00273 -0.00112 C4 1 -0.799582 -0.848520 -0.694732 11.00000 0.01850 0.01553 = 0.01912 -0.00110 0.00250 -0.00090 C5 1 -0.670055 -0.736748 -0.689438 11.00000 0.01601 0.01977 = 0.01101 -0.00002 0.00114 -0.00011 C6 1 -0.578614 -0.686150 -0.651092 11.00000 0.01756 0.01467 = 0.02147 0.00160 -0.00186 0.00206 C7 1 -0.448018 -0.575281 -0.611651 11.00000 0.01391 0.01884 = 0.01514 -0.00191 0.00199 -0.00206 C8 1 -0.381443 -0.618851 -0.526439 11.00000 0.01993 0.01358 = 0.01567 -0.00020 -0.00054 -0.00272 C9 1 -0.494730 -0.457532 -0.761446 11.00000 0.02689 0.01920 = 0.01927 0.00757 0.00393 -0.00082 AFIX 23 H9A 2 -0.432992 -0.431202 -0.808848 11.00000 -1.20000 H9B 2 -0.533178 -0.494802 -0.816885 11.00000 -1.20000 AFIX 0 C10 1 -0.610647 -0.413055 -0.730930 11.00000 0.02019 0.02362 = 0.01964 -0.00565 0.00056 -0.00706 AFIX 13 H10 2 -0.672099 -0.439368 -0.681623 11.00000 -1.20000 AFIX 0 C11 1 -0.693794 -0.386128 -0.851060 11.00000 0.02666 0.03139 = 0.03288 0.00484 0.00256 0.00592 AFIX 137 H11A 2 -0.775769 -0.363319 -0.829309 11.00000 -1.50000 H11C 2 -0.721481 -0.423326 -0.909352 11.00000 -1.50000 H11B 2 -0.637929 -0.354317 -0.892247 11.00000 -1.50000 AFIX 0 C12 1 -0.236281 -0.658260 -0.295632 11.00000 0.02369 0.01915 = 0.02336 0.00692 -0.00371 0.00002 AFIX 23 H12A 2 -0.320927 -0.651052 -0.256461 11.00000 -1.20000 H12B 2 -0.236865 -0.704920 -0.327566 11.00000 -1.20000 AFIX 0 C13 1 -0.110608 -0.646962 -0.197021 11.00000 0.02007 0.02073 = 0.02050 0.00367 -0.00088 0.00284 AFIX 13 H13 2 -0.025726 -0.649027 -0.239196 11.00000 -1.20000 AFIX 0 C14 1 -0.104305 -0.700434 -0.094954 11.00000 0.03935 0.02237 = 0.02491 0.00830 0.00064 0.00879 AFIX 137 H14B 2 -0.028937 -0.690394 -0.027138 11.00000 -1.50000 H14C 2 -0.088649 -0.744261 -0.132216 11.00000 -1.50000 H14A 2 -0.191251 -0.701246 -0.059464 11.00000 -1.50000 AFIX 0 C15 1 0.022707 -0.475765 -0.754319 11.00000 0.06035 0.02350 = 0.05856 0.00335 -0.01959 -0.01716 AFIX 23 H15A 2 0.096317 -0.492963 -0.800675 11.00000 -1.20000 H15B 2 0.035615 -0.426685 -0.745270 11.00000 -1.20000 AFIX 0 C16 1 0.040745 -0.504764 -0.629610 11.00000 0.05338 0.02429 = 0.06714 0.00995 -0.01429 -0.00748 AFIX 23 H16A 2 -0.036957 -0.490548 -0.585516 11.00000 -1.20000 H16B 2 0.125669 -0.486107 -0.581396 11.00000 -1.20000 AFIX 0 C17 1 -0.169965 -0.574097 -0.813352 11.00000 0.02319 0.01618 = 0.01276 -0.00225 0.00353 -0.00429 C18 1 -0.096735 -0.614153 -0.725391 11.00000 0.01729 0.01159 = 0.01970 -0.00019 0.00279 0.00076 C19 1 -0.298941 -0.685866 -0.828002 11.00000 0.01577 0.01385 = 0.01824 -0.00194 0.00260 -0.00216 C20 1 -0.391102 -0.736761 -0.866051 11.00000 0.01788 0.01499 = 0.01761 -0.00078 0.00242 0.00016 C21 1 -0.586809 -0.804904 -0.987273 11.00000 0.01569 0.01635 = 0.01676 -0.00180 0.00025 -0.00128 C22 1 -0.518016 -0.848828 -0.901657 11.00000 0.01442 0.01509 = 0.02095 -0.00393 0.00231 -0.00043 C23 1 -0.738855 -0.765288 -1.211718 11.00000 0.02676 0.02566 = 0.02312 0.00627 0.00039 -0.00414 AFIX 23 H23B 2 -0.769042 -0.720935 -1.184089 11.00000 -1.20000 H23A 2 -0.645101 -0.760561 -1.234817 11.00000 -1.20000 AFIX 0 C24 1 -0.835962 -0.789748 -1.325252 11.00000 0.02720 0.02529 = 0.01851 0.00137 0.00316 -0.00172 AFIX 13 H24 2 -0.795567 -0.829943 -1.362586 11.00000 -1.20000 AFIX 0 C25 1 -0.860540 -0.735294 -1.425179 11.00000 0.03237 0.03356 = 0.02413 0.00734 0.00308 0.00608 AFIX 137 H25C 2 -0.916900 -0.753123 -1.501164 11.00000 -1.50000 H25A 2 -0.772296 -0.719900 -1.447687 11.00000 -1.50000 H25B 2 -0.908341 -0.697596 -1.391396 11.00000 -1.50000 AFIX 0 C26 1 -0.423003 -0.962922 -0.775430 11.00000 0.01890 0.01638 = 0.02588 0.00114 -0.00322 -0.00245 AFIX 23 H26B 2 -0.339202 -0.963320 -0.817659 11.00000 -1.20000 H26A 2 -0.406140 -0.933519 -0.699670 11.00000 -1.20000 AFIX 0 C27 1 -0.456051 -1.034174 -0.734968 11.00000 0.02117 0.01750 = 0.02928 0.00531 0.00665 -0.00099 AFIX 13 H27 2 -0.541262 -1.032170 -0.693275 11.00000 -1.20000 AFIX 0 C28 1 -0.339706 -1.059101 -0.637110 11.00000 0.03287 0.03072 = 0.02802 0.00818 -0.00040 0.00526 AFIX 137 H28B 2 -0.362053 -1.103896 -0.607972 11.00000 -1.50000 H28C 2 -0.327221 -1.028282 -0.564452 11.00000 -1.50000 H28A 2 -0.254781 -1.061205 -0.675773 11.00000 -1.50000 AFIX 0 H1 2 -0.603813 -0.346488 -0.603904 11.00000 0.06688 H2 2 -0.057210 -0.572962 -0.089043 11.00000 0.03701 H3 2 -1.017395 -0.820540 -1.341865 11.00000 0.06525 H4 2 -0.403332 -1.083730 -0.865395 11.00000 0.03197 HKLF 4 REM ssbr3_Gabsnew in P2(1) REM R1 = 0.0342 for 6862 Fo > 4sig(Fo) and 0.0375 for all 7282 data REM 471 parameters refined using 6 restraints END WGHT 0.0330 0.5162 REM Highest difference peak 0.832, deepest hole -0.483, 1-sigma level 0.086 Q1 1 0.0888 -0.5155 -0.6977 11.00000 0.05 0.83 Q2 1 -0.0379 -0.4622 -0.7086 11.00000 0.05 0.66 Q3 1 -0.8421 -0.5809 -0.9367 11.00000 0.05 0.50 Q4 1 -0.1316 -0.8529 -0.5862 11.00000 0.05 0.46 Q5 1 -0.8577 -0.5706 -1.1138 11.00000 0.05 0.44 Q6 1 -0.7680 -0.5793 -1.0930 11.00000 0.05 0.43 Q7 1 -1.0916 -0.9089 -0.7816 11.00000 0.05 0.42 Q8 1 -0.1375 -0.8432 -0.4029 11.00000 0.05 0.42 Q9 1 -0.8869 -0.9362 -0.5601 11.00000 0.05 0.41 Q10 1 -0.7142 -0.5563 -1.1018 11.00000 0.05 0.41 Q11 1 -0.4487 -0.6403 -0.5143 11.00000 0.05 0.39 Q12 1 -0.0914 -0.8358 -0.4813 11.00000 0.05 0.38 Q13 1 -0.1601 -0.8188 -0.5809 11.00000 0.05 0.38 Q14 1 -0.7939 -0.6200 -0.9863 11.00000 0.05 0.38 Q15 1 -0.1804 -0.8052 -0.4525 11.00000 0.05 0.38 Q16 1 0.0641 -0.5504 -0.6254 11.00000 0.05 0.37 Q17 1 -0.7253 -0.3697 -0.5781 11.00000 0.05 0.36 Q18 1 -0.2396 -0.8319 -0.4255 11.00000 0.05 0.36 Q19 1 -0.9489 -0.9625 -0.8001 11.00000 0.05 0.36 Q20 1 -0.1399 -0.5419 -0.8454 11.00000 0.05 0.36 ; _shelx_res_checksum 16537 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 _atom_site_refinement_flags_adp Br1 Br -0.19334(6) -0.84976(3) -0.50717(5) 0.02559(14) Uani 1 1 d . . Br2 Br -0.79595(5) -0.57204(3) -1.01467(6) 0.02808(15) Uani 1 1 d . . S1 S -1.02464(13) -0.83133(7) -0.87998(14) 0.0217(3) Uani 1 1 d . . S2 S -0.82840(15) -0.93011(8) -0.64640(15) 0.0262(3) Uani 1 1 d . . S3 S -0.81123(13) -0.72924(7) -0.80440(13) 0.0173(3) Uani 1 1 d . . S4 S -0.64687(13) -0.81491(7) -0.61899(13) 0.0182(3) Uani 1 1 d . . S5 S -0.58781(12) -0.60591(7) -0.71352(13) 0.0177(3) Uani 1 1 d . . S6 S -0.44303(14) -0.70095(7) -0.53198(14) 0.0203(3) Uani 1 1 d . . S7 S -0.39601(15) -0.49190(8) -0.61811(16) 0.0264(3) Uani 1 1 d . . S8 S -0.23110(13) -0.59977(7) -0.42683(13) 0.0195(3) Uani 1 1 d . . S9 S -0.14129(15) -0.49095(8) -0.85178(15) 0.0245(3) Uani 1 1 d . . S10 S 0.05158(13) -0.59430(7) -0.62339(15) 0.0221(3) Uani 1 1 d . . S11 S -0.31699(13) -0.60831(7) -0.89805(14) 0.0188(3) Uani 1 1 d . . S12 S -0.15949(13) -0.69497(7) -0.71096(13) 0.0173(3) Uani 1 1 d . . S13 S -0.52771(13) -0.72308(7) -0.98345(14) 0.0194(3) Uani 1 1 d . . S14 S -0.37893(13) -0.81586(7) -0.80149(13) 0.0176(3) Uani 1 1 d . . S15 S -0.73854(13) -0.82592(7) -1.08321(14) 0.0193(3) Uani 1 1 d . . S16 S -0.56739(13) -0.93129(7) -0.88458(14) 0.0199(3) Uani 1 1 d . . O1 O -0.5482(4) -0.3599(2) -0.6532(4) 0.0316(10) Uani 1 1 d D . O2 O -0.1240(4) -0.5822(2) -0.1461(4) 0.0278(9) Uani 1 1 d D . O3 O -0.9603(4) -0.8085(2) -1.2783(4) 0.0308(10) Uani 1 1 d D . O4 O -0.4811(4) -1.0778(2) -0.8407(4) 0.0280(10) Uani 1 1 d D . C1 C -1.0122(6) -0.9217(3) -0.8661(6) 0.0267(14) Uani 1 1 d . . H1B H -1.0954 -0.9420 -0.9143 0.032 Uiso 1 1 calc R U H1A H -0.9321 -0.9371 -0.9056 0.032 Uiso 1 1 calc R U C2 C -0.9977(5) -0.9462(3) -0.7319(6) 0.0242(13) Uani 1 1 d . . H2B H -1.0158 -0.9950 -0.7319 0.029 Uiso 1 1 calc R U H2A H -1.0672 -0.9238 -0.6871 0.029 Uiso 1 1 calc R U C3 C -0.8737(5) -0.8097(3) -0.7829(5) 0.0165(11) Uani 1 1 d . . C4 C -0.7996(5) -0.8485(3) -0.6947(5) 0.0177(11) Uani 1 1 d . . C5 C -0.6701(5) -0.7367(3) -0.6894(5) 0.0157(11) Uani 1 1 d . . C6 C -0.5786(5) -0.6862(3) -0.6511(5) 0.0183(12) Uani 1 1 d . . C7 C -0.4480(5) -0.5753(3) -0.6117(5) 0.0160(11) Uani 1 1 d . . C8 C -0.3814(5) -0.6189(3) -0.5264(5) 0.0167(11) Uani 1 1 d . . C9 C -0.4947(5) -0.4575(3) -0.7614(5) 0.0217(12) Uani 1 1 d . . H9A H -0.4330 -0.4312 -0.8088 0.026 Uiso 1 1 calc R U H9B H -0.5332 -0.4948 -0.8169 0.026 Uiso 1 1 calc R U C10 C -0.6106(5) -0.4131(3) -0.7309(5) 0.0214(12) Uani 1 1 d . . H10 H -0.6721 -0.4394 -0.6816 0.026 Uiso 1 1 calc DR U C11 C -0.6938(6) -0.3861(3) -0.8511(6) 0.0304(15) Uani 1 1 d . . H11A H -0.7758 -0.3633 -0.8293 0.046 Uiso 1 1 calc R U H11C H -0.7215 -0.4233 -0.9094 0.046 Uiso 1 1 calc R U H11B H -0.6379 -0.3543 -0.8922 0.046 Uiso 1 1 calc R U C12 C -0.2363(6) -0.6583(3) -0.2956(6) 0.0227(13) Uani 1 1 d . . H12A H -0.3209 -0.6511 -0.2565 0.027 Uiso 1 1 calc R U H12B H -0.2369 -0.7049 -0.3276 0.027 Uiso 1 1 calc R U C13 C -0.1106(5) -0.6470(3) -0.1970(5) 0.0208(12) Uani 1 1 d . . H13 H -0.0257 -0.6490 -0.2392 0.025 Uiso 1 1 calc R U C14 C -0.1043(6) -0.7004(3) -0.0950(6) 0.0292(14) Uani 1 1 d . . H14B H -0.0289 -0.6904 -0.0271 0.044 Uiso 1 1 calc R U H14C H -0.0886 -0.7443 -0.1322 0.044 Uiso 1 1 calc R U H14A H -0.1913 -0.7012 -0.0595 0.044 Uiso 1 1 calc R U C15 C 0.0227(8) -0.4758(4) -0.7543(8) 0.050(2) Uani 1 1 d . . H15A H 0.0963 -0.4930 -0.8007 0.060 Uiso 1 1 calc R U H15B H 0.0356 -0.4267 -0.7453 0.060 Uiso 1 1 calc R U C16 C 0.0407(8) -0.5048(4) -0.6296(8) 0.050(2) Uani 1 1 d . . H16A H -0.0370 -0.4905 -0.5855 0.060 Uiso 1 1 calc R U H16B H 0.1257 -0.4861 -0.5814 0.060 Uiso 1 1 calc R U C17 C -0.1700(5) -0.5741(3) -0.8134(5) 0.0173(11) Uani 1 1 d . . C18 C -0.0967(5) -0.6142(3) -0.7254(5) 0.0162(11) Uani 1 1 d . . C19 C -0.2989(5) -0.6859(3) -0.8280(5) 0.0159(11) Uani 1 1 d . . C20 C -0.3911(5) -0.7368(3) -0.8661(5) 0.0168(11) Uani 1 1 d . . C21 C -0.5868(5) -0.8049(3) -0.9873(5) 0.0164(11) Uani 1 1 d . . C22 C -0.5180(5) -0.8488(3) -0.9017(5) 0.0168(11) Uani 1 1 d . . C23 C -0.7389(6) -0.7653(3) -1.2117(6) 0.0255(13) Uani 1 1 d . . H23B H -0.7690 -0.7209 -1.1841 0.031 Uiso 1 1 calc R U H23A H -0.6451 -0.7606 -1.2348 0.031 Uiso 1 1 calc R U C24 C -0.8360(6) -0.7897(3) -1.3253(5) 0.0237(13) Uani 1 1 d . . H24 H -0.7956 -0.8299 -1.3626 0.028 Uiso 1 1 calc R U C25 C -0.8605(6) -0.7353(3) -1.4252(6) 0.0301(14) Uani 1 1 d . . H25C H -0.9169 -0.7531 -1.5012 0.045 Uiso 1 1 calc R U H25A H -0.7723 -0.7199 -1.4477 0.045 Uiso 1 1 calc R U H25B H -0.9083 -0.6976 -1.3914 0.045 Uiso 1 1 calc R U C26 C -0.4230(5) -0.9629(3) -0.7754(5) 0.0210(12) Uani 1 1 d . . H26B H -0.3392 -0.9633 -0.8177 0.025 Uiso 1 1 calc R U H26A H -0.4061 -0.9335 -0.6997 0.025 Uiso 1 1 calc R U C27 C -0.4561(5) -1.0342(3) -0.7350(6) 0.0224(12) Uani 1 1 d . . H27 H -0.5413 -1.0322 -0.6933 0.027 Uiso 1 1 calc R U C28 C -0.3397(6) -1.0591(3) -0.6371(6) 0.0310(15) Uani 1 1 d . . H28B H -0.3621 -1.1039 -0.6080 0.046 Uiso 1 1 calc R U H28C H -0.3272 -1.0283 -0.5645 0.046 Uiso 1 1 calc R U H28A H -0.2548 -1.0612 -0.6758 0.046 Uiso 1 1 calc R U H1 H -0.604(3) -0.3465(11) -0.604(3) 0.07(3) Uiso 1 1 d D . H2 H -0.057(3) -0.573(3) -0.089(3) 0.037(19) Uiso 1 1 d D . H3 H -1.017(5) -0.821(3) -1.342(4) 0.07(3) Uiso 1 1 d D . H4 H -0.403(2) -1.084(3) -0.865(5) 0.032(18) Uiso 1 1 d D . 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 0.0255(3) 0.0291(4) 0.0208(3) 0.0032(3) -0.0018(2) 0.0013(3) Br2 0.0260(3) 0.0284(4) 0.0289(3) 0.0045(3) 0.0003(2) 0.0032(3) S1 0.0171(6) 0.0200(8) 0.0263(8) 0.0017(6) -0.0031(5) -0.0022(6) S2 0.0269(7) 0.0172(8) 0.0327(9) 0.0086(7) -0.0021(6) -0.0042(6) S3 0.0162(6) 0.0142(7) 0.0204(7) 0.0014(6) -0.0016(5) 0.0009(5) S4 0.0192(6) 0.0164(7) 0.0177(7) 0.0020(6) -0.0019(5) 0.0010(5) S5 0.0152(6) 0.0174(7) 0.0193(7) 0.0027(6) -0.0016(5) 0.0001(5) S6 0.0211(6) 0.0170(8) 0.0209(7) 0.0022(6) -0.0039(5) -0.0020(6) S7 0.0259(7) 0.0191(8) 0.0309(8) 0.0054(7) -0.0075(6) -0.0044(6) S8 0.0191(6) 0.0194(8) 0.0185(7) 0.0028(6) -0.0031(5) -0.0032(6) S9 0.0274(7) 0.0170(8) 0.0286(8) 0.0067(7) 0.0022(6) -0.0032(6) S10 0.0180(6) 0.0185(8) 0.0284(8) -0.0004(7) -0.0016(6) -0.0040(6) S11 0.0201(6) 0.0161(7) 0.0193(7) 0.0020(6) -0.0005(5) 0.0002(6) S12 0.0161(6) 0.0133(7) 0.0215(7) 0.0006(6) -0.0006(5) -0.0004(5) S13 0.0209(6) 0.0153(8) 0.0203(7) 0.0029(6) -0.0033(5) -0.0016(5) S14 0.0156(6) 0.0147(7) 0.0214(7) 0.0020(6) -0.0017(5) -0.0004(5) S15 0.0184(6) 0.0188(8) 0.0193(7) 0.0022(6) -0.0024(5) -0.0035(5) S16 0.0185(6) 0.0148(7) 0.0248(7) 0.0022(6) -0.0028(5) -0.0023(5) O1 0.030(2) 0.025(3) 0.038(3) -0.012(2) 0.001(2) -0.0034(19) O2 0.031(2) 0.020(2) 0.030(2) -0.001(2) -0.0069(19) -0.0018(19) O3 0.025(2) 0.045(3) 0.021(2) 0.003(2) -0.0023(17) -0.011(2) O4 0.027(2) 0.021(2) 0.036(2) -0.005(2) 0.0028(18) -0.0066(18) C1 0.030(3) 0.020(3) 0.028(3) -0.006(3) -0.003(3) -0.006(3) C2 0.023(3) 0.021(3) 0.029(3) 0.000(3) 0.002(2) -0.006(2) C3 0.015(2) 0.018(3) 0.017(3) -0.001(2) 0.003(2) -0.001(2) C4 0.018(2) 0.016(3) 0.019(3) -0.001(3) 0.002(2) -0.001(2) C5 0.016(2) 0.020(3) 0.011(3) 0.000(2) 0.001(2) 0.000(2) C6 0.018(2) 0.015(3) 0.021(3) 0.002(3) -0.002(2) 0.002(2) C7 0.014(2) 0.019(3) 0.015(3) -0.002(3) 0.0020(19) -0.002(2) C8 0.020(2) 0.014(3) 0.016(3) 0.000(2) -0.001(2) -0.003(2) C9 0.027(3) 0.019(3) 0.019(3) 0.008(3) 0.004(2) -0.001(2) C10 0.020(3) 0.024(3) 0.020(3) -0.006(3) 0.001(2) -0.007(2) C11 0.027(3) 0.031(4) 0.033(4) 0.005(3) 0.003(3) 0.006(3) C12 0.024(3) 0.019(3) 0.023(3) 0.007(3) -0.004(2) 0.000(2) C13 0.020(3) 0.021(3) 0.020(3) 0.004(3) -0.001(2) 0.003(2) C14 0.039(3) 0.022(3) 0.025(3) 0.008(3) 0.001(3) 0.009(3) C15 0.060(5) 0.023(4) 0.059(5) 0.003(4) -0.020(4) -0.017(4) C16 0.053(4) 0.024(4) 0.067(6) 0.010(4) -0.014(4) -0.007(3) C17 0.023(2) 0.016(3) 0.013(2) -0.002(2) 0.004(2) -0.004(2) C18 0.017(2) 0.012(3) 0.020(3) 0.000(2) 0.003(2) 0.001(2) C19 0.016(2) 0.014(3) 0.018(3) -0.002(2) 0.003(2) -0.002(2) C20 0.018(2) 0.015(3) 0.018(3) -0.001(2) 0.002(2) 0.000(2) C21 0.016(2) 0.016(3) 0.017(3) -0.002(2) 0.000(2) -0.001(2) C22 0.014(2) 0.015(3) 0.021(3) -0.004(3) 0.002(2) 0.000(2) C23 0.027(3) 0.026(3) 0.023(3) 0.006(3) 0.000(2) -0.004(3) C24 0.027(3) 0.025(3) 0.019(3) 0.001(3) 0.003(2) -0.002(2) C25 0.032(3) 0.034(4) 0.024(3) 0.007(3) 0.003(3) 0.006(3) C26 0.019(3) 0.016(3) 0.026(3) 0.001(3) -0.003(2) -0.002(2) C27 0.021(3) 0.018(3) 0.029(3) 0.005(3) 0.007(2) -0.001(2) C28 0.033(3) 0.031(4) 0.028(3) 0.008(3) 0.000(3) 0.005(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 C3 S1 C1 99.0(3) C4 S2 C2 101.2(3) C5 S3 C3 95.2(3) C5 S4 C4 95.4(3) C6 S5 C7 95.3(3) C6 S6 C8 95.4(3) C7 S7 C9 105.4(3) C8 S8 C12 102.3(3) C17 S9 C15 100.7(3) C18 S10 C16 99.4(3) C19 S11 C17 95.8(3) C19 S12 C18 95.5(3) C20 S13 C21 95.4(3) C20 S14 C22 95.6(3) C21 S15 C23 101.0(3) C22 S16 C26 101.0(2) C2 C1 S1 113.5(4) C1 C2 S2 112.4(4) C4 C3 S1 127.2(4) C4 C3 S3 116.9(4) S1 C3 S3 115.9(3) C3 C4 S4 116.8(4) C3 C4 S2 130.2(4) S4 C4 S2 112.9(3) C6 C5 S3 125.2(4) C6 C5 S4 119.4(4) S3 C5 S4 115.4(3) C5 C6 S5 124.6(4) C5 C6 S6 119.8(4) S5 C6 S6 115.6(3) C8 C7 S5 117.2(4) C8 C7 S7 121.3(4) S5 C7 S7 121.5(3) C7 C8 S8 123.9(4) C7 C8 S6 116.5(4) S8 C8 S6 119.3(3) C10 C9 S7 111.9(4) O1 C10 C9 106.3(4) O1 C10 C11 111.2(5) C9 C10 C11 111.3(5) C13 C12 S8 109.0(4) O2 C13 C14 111.6(5) O2 C13 C12 106.8(4) C14 C13 C12 109.7(5) C16 C15 S9 116.5(6) C15 C16 S10 115.9(6) C18 C17 S11 116.8(4) C18 C17 S9 129.4(4) S11 C17 S9 113.8(3) C17 C18 S10 127.9(4) C17 C18 S12 116.4(4) S10 C18 S12 115.7(3) C20 C19 S11 120.7(4) C20 C19 S12 123.8(4) S11 C19 S12 115.5(3) C19 C20 S14 123.4(4) C19 C20 S13 120.6(4) S14 C20 S13 116.0(3) C22 C21 S13 116.9(4) C22 C21 S15 122.6(4) S13 C21 S15 120.0(3) C21 C22 S16 123.8(4) C21 C22 S14 115.9(4) S16 C22 S14 120.2(3) C24 C23 S15 108.5(4) O3 C24 C23 106.5(5) O3 C24 C25 111.6(5) C23 C24 C25 110.4(5) C27 C26 S16 108.9(4) O4 C27 C28 112.0(5) O4 C27 C26 111.7(5) C28 C27 C26 109.0(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C3 1.740(5) S1 C1 1.812(6) S2 C4 1.741(6) S2 C2 1.811(6) S3 C5 1.724(5) S3 C3 1.745(6) S4 C5 1.730(6) S4 C4 1.737(5) S5 C6 1.729(6) S5 C7 1.738(5) S6 C6 1.732(5) S6 C8 1.744(6) S7 C7 1.744(6) S7 C9 1.822(5) S8 C8 1.737(5) S8 C12 1.821(6) S9 C17 1.740(6) S9 C15 1.817(7) S10 C18 1.738(5) S10 C16 1.789(8) S11 C19 1.714(6) S11 C17 1.734(5) S12 C19 1.728(5) S12 C18 1.740(5) S13 C20 1.724(5) S13 C21 1.731(6) S14 C20 1.717(6) S14 C22 1.742(5) S15 C21 1.738(5) S15 C23 1.821(6) S16 C22 1.731(6) S16 C26 1.817(5) O1 C10 1.428(7) O2 C13 1.413(7) O3 C24 1.431(7) O4 C27 1.414(7) C1 C2 1.492(8) C3 C4 1.348(8) C5 C6 1.375(7) C7 C8 1.356(8) C9 C10 1.514(7) C10 C11 1.515(8) C12 C13 1.522(7) C13 C14 1.515(8) C15 C16 1.432(10) C17 C18 1.357(8) C19 C20 1.383(7) C21 C22 1.371(8) C23 C24 1.511(8) C24 C25 1.513(8) C26 C27 1.532(7) C27 C28 1.519(8) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 Br1 0.8500 2.451 3.251(4) 157.1 2_454 O2 H2 Br2 0.8500 2.58 3.340(4) 149 1_656 O3 H3 Br1 0.8500 2.361 3.208(4) 174 1_454 O4 H4 Br2 0.8500 2.488 3.306(4) 162 2_443 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 C3 S1 C1 C2 55.9(5) S1 C1 C2 S2 -73.5(5) C4 S2 C2 C1 43.2(5) C1 S1 C3 C4 -18.6(5) C1 S1 C3 S3 160.4(3) C5 S3 C3 C4 -0.9(5) C5 S3 C3 S1 179.9(3) S1 C3 C4 S4 176.1(3) S3 C3 C4 S4 -3.0(6) S1 C3 C4 S2 -1.2(8) S3 C3 C4 S2 179.7(3) C5 S4 C4 C3 5.2(5) C5 S4 C4 S2 -177.1(3) C2 S2 C4 C3 -7.0(6) C2 S2 C4 S4 175.6(3) C3 S3 C5 C6 -175.1(5) C3 S3 C5 S4 4.4(3) C4 S4 C5 C6 173.9(4) C4 S4 C5 S3 -5.7(3) S3 C5 C6 S5 -1.0(7) S4 C5 C6 S5 179.5(3) S3 C5 C6 S6 178.8(3) S4 C5 C6 S6 -0.7(6) C7 S5 C6 C5 177.0(5) C7 S5 C6 S6 -2.9(4) C8 S6 C6 C5 -176.5(5) C8 S6 C6 S5 3.3(4) C6 S5 C7 C8 1.0(5) C6 S5 C7 S7 -178.7(3) C9 S7 C7 C8 170.7(4) C9 S7 C7 S5 -9.7(4) S5 C7 C8 S8 174.1(3) S7 C7 C8 S8 -6.3(7) S5 C7 C8 S6 1.2(6) S7 C7 C8 S6 -179.2(3) C12 S8 C8 C7 155.7(5) C12 S8 C8 S6 -31.6(4) C6 S6 C8 C7 -2.7(5) C6 S6 C8 S8 -175.9(3) C7 S7 C9 C10 104.1(4) S7 C9 C10 O1 60.0(5) S7 C9 C10 C11 -178.7(4) C8 S8 C12 C13 -179.0(4) S8 C12 C13 O2 65.6(5) S8 C12 C13 C14 -173.3(4) C17 S9 C15 C16 -39.3(7) S9 C15 C16 S10 68.4(8) C18 S10 C16 C15 -52.4(7) C19 S11 C17 C18 -1.6(5) C19 S11 C17 S9 -179.7(3) C15 S9 C17 C18 5.8(6) C15 S9 C17 S11 -176.4(4) S11 C17 C18 S10 -178.3(3) S9 C17 C18 S10 -0.6(8) S11 C17 C18 S12 0.8(6) S9 C17 C18 S12 178.5(3) C16 S10 C18 C17 18.9(6) C16 S10 C18 S12 -160.2(4) C19 S12 C18 C17 0.5(5) C19 S12 C18 S10 179.7(3) C17 S11 C19 C20 -177.4(4) C17 S11 C19 S12 2.0(3) C18 S12 C19 C20 177.7(5) C18 S12 C19 S11 -1.6(3) S11 C19 C20 S14 179.4(3) S12 C19 C20 S14 0.1(7) S11 C19 C20 S13 -0.9(6) S12 C19 C20 S13 179.8(3) C22 S14 C20 C19 -176.7(5) C22 S14 C20 S13 3.6(3) C21 S13 C20 C19 176.4(4) C21 S13 C20 S14 -3.8(3) C20 S13 C21 C22 2.6(4) C20 S13 C21 S15 175.2(3) C23 S15 C21 C22 -158.0(5) C23 S15 C21 S13 29.8(4) S13 C21 C22 S16 176.2(3) S15 C21 C22 S16 3.7(7) S13 C21 C22 S14 -0.6(6) S15 C21 C22 S14 -173.0(3) C26 S16 C22 C21 172.4(5) C26 S16 C22 S14 -11.0(4) C20 S14 C22 C21 -1.8(4) C20 S14 C22 S16 -178.6(3) C21 S15 C23 C24 161.3(4) S15 C23 C24 O3 47.9(5) S15 C23 C24 C25 169.3(4) C22 S16 C26 C27 173.0(4) S16 C26 C27 O4 59.4(5) S16 C26 C27 C28 -176.3(4)