#------------------------------------------------------------------------------ #$Date: 2021-10-06 16:41:29 +0300 (Wed, 06 Oct 2021) $ #$Revision: 269602 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128944.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_7128944 loop_ _publ_author_name 'Dzieszkowski, Krzysztof' 'S\/lotwi\'nski, Micha\/l' 'Rafi\'nska, Katarzyna' 'Muzio\/l, Tadeusz M' 'Rafi\'nski, Zbigniew' _publ_section_title ; NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenones via \a,\b-unsaturated acyl azoliums. ; _journal_issue 78 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 9999 _journal_page_last 10002 _journal_paper_doi 10.1039/d1cc03708k _journal_volume 57 _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C19 H15 Br O5' _chemical_formula_sum 'C19 H15 Br O5' _chemical_formula_weight 403.22 _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_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/1 _audit_update_record ; 2021-06-07 deposited with the CCDC. 2021-08-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 115.06(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.401(8) _cell_length_b 5.9984(13) _cell_length_c 18.889(6) _cell_measurement_reflns_used 2406 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.2770 _cell_measurement_theta_min 2.1760 _cell_volume 1786.0(13) _computing_data_collection 'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)' _computing_publication_material ciftab _computing_structure_refinement 'SHELXL-2018/1 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_unetI/netI 0.0778 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 11460 _diffrn_reflns_point_group_measured_fraction_full 0.930 _diffrn_reflns_point_group_measured_fraction_max 0.919 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 2.095 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 2.327 _exptl_absorpt_correction_T_max 0.869 _exptl_absorpt_correction_T_min 0.320 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details 'CrysAlisPro 1.171.38.34a (2015)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.500 _exptl_crystal_description needle _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.550 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.247 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.051 _refine_ls_abs_structure_details ; Flack x determined using 1078 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.014(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 466 _refine_ls_number_reflns 6739 _refine_ls_number_restraints 17 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.1233 _refine_ls_R_factor_gt 0.0551 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0546P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1122 _refine_ls_wR_factor_ref 0.1451 _reflns_Friedel_coverage 0.673 _reflns_Friedel_fraction_full 0.844 _reflns_Friedel_fraction_max 0.822 _reflns_number_gt 3655 _reflns_number_total 6739 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc03708k2.cif _cod_data_source_block kd2shape _cod_depositor_comments 'Adding full bibliography for 7128944.cif.' _cod_original_cell_volume 1786.1(13) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7128944 _shelx_shelxl_version_number 2018/1 _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_min 0.361 _shelx_estimated_absorpt_t_max 0.893 _shelx_res_file ; TITL kd2shape in P2(1) kd2shape.res created by SHELXL-2018/1 at 00:55:15 on 02-Dec-2020 REM P2(1) (#4 in standard setting) CELL 0.71073 17.401148 5.998359 18.888831 90.0000 115.0553 90.0000 ZERR 4.00 0.008375 0.001332 0.006033 0.0000 0.0491 0.0000 LATT -1 SYMM -x, y+1/2,-z SFAC C H O Br UNIT 76.00 60.00 20.00 4.00 MERG 2 SHEL 20 0.8 TEMP 20.00 SIZE 0.55 0.12 0.05 ACTA CONF LIST 6 FREE C43 C46 DFIX 0.82 0.06 O7 H7 O37 H37 DFIX 1.25 C43 O44 C43 O45 C43 O47 C43 O48 DFIX 1.45 0.03 O45 C46 O48 C49 FLAT C42 C43 O44 O45 FLAT C42 C43 O47 O48 rem ISOR 0.02 O48 C49 C43 O45 C46 ISOR 0.02 C43 EADP O45 O47 EADP O44 O48 EADP C46 C49 rem TWIN 1.000 0.000 0.000 0.000 -1.000 0.000 -0.924 0.000 -1.000 2 rem TWIN -1.000 0.000 0.000 0.000 1.000 0.000 0.000 0.000 -1.000 2 rem TWIN -1.000 0.000 0.000 0.000 -1.000 0.000 0.924 0.000 1.000 2 rem BASF 0.2 L.S. 20 FMAP 2 PLAN 25 BOND $H WGHT 0.054600 FVAR 1.49323 BR1 4 0.867743 0.125919 0.583605 11.00000 0.12575 0.14818 = 0.07887 0.04370 0.04955 0.00023 C1 1 0.879120 0.168169 0.490075 11.00000 0.07044 0.07733 = 0.07078 0.02978 0.02162 0.00110 C2 1 0.924807 0.016039 0.468613 11.00000 0.08740 0.06477 = 0.05839 0.02027 0.01075 0.00314 AFIX 43 H2 2 0.948527 -0.107055 0.500323 11.00000 -1.20000 AFIX 0 C3 1 0.935903 0.042449 0.401846 11.00000 0.08747 0.04538 = 0.05821 0.00529 0.00466 0.00784 AFIX 43 H3 2 0.966971 -0.060652 0.387892 11.00000 -1.20000 AFIX 0 C4 1 0.899484 0.228109 0.354889 11.00000 0.06304 0.05166 = 0.04259 0.00115 0.01252 -0.00832 O5 3 0.912151 0.249873 0.289009 11.00000 0.08275 0.05358 = 0.05544 0.00807 0.02867 0.01625 C6 1 0.880780 0.431761 0.241103 11.00000 0.07578 0.04644 = 0.04419 0.00543 0.02207 0.00104 C7 1 0.837687 0.590604 0.258555 11.00000 0.06790 0.04185 = 0.04791 0.00562 0.02359 -0.00147 O7 3 0.810452 0.773608 0.209958 11.00000 0.08020 0.05143 = 0.07287 0.01398 0.04270 0.01001 H7 2 0.775772 0.832104 0.217596 11.00000 -1.20000 C8 1 0.815191 0.573854 0.322515 11.00000 0.07084 0.04994 = 0.05473 0.00358 0.02805 -0.00065 O8 3 0.768838 0.710296 0.334314 11.00000 0.08849 0.07115 = 0.07633 0.01253 0.04965 0.01670 C9 1 0.852380 0.383458 0.373977 11.00000 0.06149 0.04981 = 0.05221 0.00472 0.01590 -0.00143 C10 1 0.840843 0.350463 0.442982 11.00000 0.07031 0.06964 = 0.05413 0.00900 0.02522 -0.00202 AFIX 43 H10 2 0.808151 0.449245 0.456605 11.00000 -1.20000 AFIX 0 C11 1 0.900853 0.421839 0.171686 11.00000 0.06718 0.05515 = 0.04934 0.00043 0.02446 0.00446 AFIX 13 H11 2 0.872513 0.547562 0.137425 11.00000 -1.20000 AFIX 0 C12 1 0.864162 0.205562 0.126636 11.00000 0.07955 0.05828 = 0.05731 0.00056 0.02806 0.00266 AFIX 23 H12A 2 0.891696 0.079497 0.159883 11.00000 -1.20000 H12B 2 0.804165 0.198052 0.114381 11.00000 -1.20000 AFIX 0 O14 3 0.872146 0.337104 0.011002 11.00000 0.22719 0.09401 = 0.07165 0.01381 0.06812 0.01089 C13 1 0.875027 0.187349 0.053355 11.00000 0.10929 0.06688 = 0.05480 -0.00342 0.03035 -0.00292 O15 3 0.887831 -0.021741 0.038764 11.00000 0.16061 0.08296 = 0.07478 -0.00799 0.06052 0.01643 C16 1 0.895407 -0.064968 -0.033732 11.00000 0.25237 0.15130 = 0.10206 -0.02149 0.11775 0.01378 AFIX 133 H16A 2 0.846660 -0.006215 -0.076832 11.00000 -1.50000 H16B 2 0.898840 -0.222799 -0.040312 11.00000 -1.50000 H16C 2 0.945725 0.005560 -0.031935 11.00000 -1.50000 AFIX 0 C21 1 0.995794 0.444919 0.196318 11.00000 0.07622 0.06173 = 0.05548 -0.00463 0.03588 0.00485 C22 1 1.028563 0.645251 0.186767 11.00000 0.10216 0.07393 = 0.12614 -0.00396 0.07705 -0.00020 AFIX 43 H22 2 0.991931 0.764463 0.164967 11.00000 -1.20000 AFIX 0 C23 1 1.113445 0.674282 0.208389 11.00000 0.10667 0.10717 = 0.15694 -0.04072 0.08755 -0.03369 AFIX 43 H23 2 1.133436 0.807598 0.197389 11.00000 -1.20000 AFIX 0 C24 1 1.169361 0.505018 0.246603 11.00000 0.08498 0.15234 = 0.11700 -0.04763 0.04693 -0.00040 AFIX 43 H24 2 1.227586 0.527925 0.266152 11.00000 -1.20000 AFIX 0 C25 1 1.138136 0.304541 0.255247 11.00000 0.08306 0.13779 = 0.10238 -0.03025 0.01288 0.02366 AFIX 43 H25 2 1.175003 0.185800 0.277089 11.00000 -1.20000 AFIX 0 C26 1 1.052785 0.275651 0.232073 11.00000 0.08583 0.08594 = 0.11542 0.00384 0.04291 0.01803 AFIX 43 H26 2 1.032848 0.139088 0.240622 11.00000 -1.20000 AFIX 0 BR2 4 0.639655 0.801853 -0.008099 11.00000 0.12009 0.10293 = 0.08615 0.03136 0.04710 0.00645 C31 1 0.606242 0.702083 0.069465 11.00000 0.06950 0.06113 = 0.05696 0.00601 0.01465 -0.00021 C32 1 0.545969 0.826991 0.083272 11.00000 0.08091 0.05500 = 0.07516 0.00240 0.02342 0.00955 AFIX 43 H32 2 0.523781 0.956810 0.055078 11.00000 -1.20000 AFIX 0 C33 1 0.520125 0.757224 0.138142 11.00000 0.07370 0.05929 = 0.07949 0.00319 0.02478 0.01316 AFIX 43 H33 2 0.479829 0.838587 0.147432 11.00000 -1.20000 AFIX 0 C34 1 0.554241 0.563222 0.180461 11.00000 0.06641 0.05239 = 0.07904 0.00247 0.03905 0.00230 O35 3 0.526706 0.501347 0.234973 11.00000 0.06835 0.05825 = 0.08015 0.00133 0.03718 0.01009 C36 1 0.558978 0.316917 0.279461 11.00000 0.06847 0.05198 = 0.07853 -0.00262 0.03933 0.00210 C37 1 0.619823 0.189313 0.272297 11.00000 0.06704 0.05239 = 0.07667 0.00173 0.03586 -0.00309 O37 3 0.649715 0.012129 0.320202 11.00000 0.09658 0.06705 = 0.09927 0.02351 0.06327 0.02448 H37 2 0.684982 -0.054154 0.310766 11.00000 -1.20000 C38 1 0.650588 0.240846 0.214286 11.00000 0.05749 0.05176 = 0.06146 -0.00396 0.02539 0.00043 O38 3 0.707358 0.124024 0.208577 11.00000 0.06770 0.05389 = 0.07312 0.00913 0.03638 0.00627 C39 1 0.614617 0.438877 0.168091 11.00000 0.06111 0.04913 = 0.05665 0.00011 0.02525 0.00323 C40 1 0.639710 0.508388 0.110072 11.00000 0.06352 0.05907 = 0.06500 -0.00408 0.02655 -0.00374 AFIX 43 H40 2 0.678421 0.424793 0.099181 11.00000 -1.20000 AFIX 0 C41 1 0.522997 0.272654 0.337702 11.00000 0.08338 0.06557 = 0.08958 -0.00588 0.05517 -0.00497 AFIX 13 H41 2 0.525249 0.110988 0.345832 11.00000 -1.20000 AFIX 0 C42 1 0.430518 0.340291 0.307945 11.00000 0.06866 0.14295 = 0.08172 -0.02728 0.03661 -0.02318 AFIX 23 H42A 2 0.411827 0.312494 0.348776 11.00000 -1.20000 H42B 2 0.426056 0.499341 0.297707 11.00000 -1.20000 AFIX 0 C43 1 0.373456 0.224416 0.237133 11.00000 0.11530 0.24533 = 0.12909 -0.03684 0.06981 -0.01352 PART 1 10.6 O44 3 0.333841 0.364780 0.181188 10.60000 0.10574 0.18028 = 0.22170 -0.11375 0.03105 -0.04928 O45 3 0.358928 0.027705 0.229472 10.60000 0.16937 0.15251 = 0.13856 -0.04913 0.02189 -0.11603 C46 1 0.305607 -0.079811 0.159640 10.60000 0.16175 0.08128 = 0.14688 -0.03814 0.07283 -0.03142 AFIX 133 H46A 2 0.255587 0.008475 0.132748 10.60000 -1.50000 H46B 2 0.289772 -0.223534 0.171499 10.60000 -1.50000 H46C 2 0.335084 -0.097723 0.127032 10.60000 -1.50000 AFIX 0 PART 2 10.4 O47 3 0.400347 0.035373 0.241018 10.40000 0.16937 0.15251 = 0.13856 -0.04913 0.02189 -0.11603 O48 3 0.307403 0.261819 0.178834 10.40000 0.10574 0.18028 = 0.22170 -0.11375 0.03105 -0.04928 C49 1 0.268753 0.036270 0.150665 10.40000 0.16175 0.08128 = 0.14688 -0.03814 0.07283 -0.03142 AFIX 133 H49A 2 0.223249 0.050082 0.099421 10.40000 -1.50000 H49B 2 0.247166 -0.022637 0.185930 10.40000 -1.50000 H49C 2 0.311179 -0.062579 0.148668 10.40000 -1.50000 AFIX 0 PART 0 C51 1 0.575674 0.377059 0.416409 11.00000 0.07292 0.08004 = 0.07418 -0.00033 0.03982 0.01094 C52 1 0.618033 0.577017 0.423810 11.00000 0.09200 0.09881 = 0.09953 -0.02111 0.04650 -0.02178 AFIX 43 H52 2 0.616007 0.649033 0.379450 11.00000 -1.20000 AFIX 0 C53 1 0.662564 0.668928 0.495402 11.00000 0.08999 0.14111 = 0.14078 -0.04691 0.04741 -0.01312 AFIX 43 H53 2 0.689405 0.805529 0.499498 11.00000 -1.20000 AFIX 0 C54 1 0.668324 0.562423 0.561604 11.00000 0.09276 0.21526 = 0.09902 -0.06301 0.01323 0.00856 AFIX 43 H54 2 0.701596 0.623076 0.610391 11.00000 -1.20000 AFIX 0 C55 1 0.625679 0.368332 0.556508 11.00000 0.15720 0.25071 = 0.07081 0.02306 0.04175 0.03347 AFIX 43 H55 2 0.627204 0.299645 0.601225 11.00000 -1.20000 AFIX 0 C56 1 0.579964 0.275099 0.483426 11.00000 0.13334 0.11272 = 0.10657 0.01347 0.06211 0.00564 AFIX 43 H56 2 0.551598 0.141025 0.479501 11.00000 -1.20000 AFIX 0 HKLF 4 REM kd2shape in P2(1) REM R1 = 0.0551 for 3655 Fo > 4sig(Fo) and 0.1233 for all 6739 data REM 466 parameters refined using 17 restraints END WGHT 0.0538 0.0000 REM Highest difference peak 0.247, deepest hole -0.254, 1-sigma level 0.051 Q1 1 0.7392 0.8283 0.0093 11.00000 0.05 0.25 Q2 1 0.8315 0.1018 0.5242 11.00000 0.05 0.25 Q3 1 0.6064 0.8172 -0.0711 11.00000 0.05 0.24 Q4 1 0.5483 0.8156 -0.0214 11.00000 0.05 0.20 Q5 1 0.5399 0.7775 -0.0511 11.00000 0.05 0.20 Q6 1 0.4293 -0.1227 0.2607 11.00000 0.05 0.20 Q7 1 0.6770 0.8259 0.0600 11.00000 0.05 0.20 Q8 1 0.8994 0.0118 0.5723 11.00000 0.05 0.19 Q9 1 0.7816 0.2872 0.0020 11.00000 0.05 0.19 Q10 1 0.4169 0.0783 0.1979 11.00000 0.05 0.19 Q11 1 0.3878 0.2051 0.1724 11.00000 0.05 0.19 Q12 1 0.7478 0.2698 0.2538 11.00000 0.05 0.19 Q13 1 0.6936 0.7278 0.0584 11.00000 0.05 0.18 Q14 1 0.9057 0.1996 0.6504 11.00000 0.05 0.18 Q15 1 0.6087 0.8581 0.0000 11.00000 0.05 0.18 Q16 1 1.0251 0.1668 0.1658 11.00000 0.05 0.18 Q17 1 0.7271 0.6850 0.0373 11.00000 0.05 0.18 Q18 1 0.9591 -0.0256 0.4707 11.00000 0.05 0.17 Q19 1 1.0007 0.6871 0.2691 11.00000 0.05 0.17 Q20 1 0.9694 0.1570 0.4763 11.00000 0.05 0.17 Q21 1 0.7847 0.3014 0.5615 11.00000 0.05 0.17 Q22 1 0.7850 0.0960 0.5765 11.00000 0.05 0.17 Q23 1 0.2008 0.0893 0.1466 11.00000 0.05 0.17 Q24 1 0.4781 0.2649 0.1434 11.00000 0.05 0.17 Q25 1 0.8837 0.2133 0.5872 11.00000 0.05 0.17 ; _shelx_res_checksum 83969 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.86774(9) 0.1259(2) 0.58360(7) 0.1155(5) Uani 1 1 d . . . . . C1 C 0.8791(6) 0.1682(17) 0.4901(5) 0.076(3) Uani 1 1 d . . . . . C2 C 0.9248(6) 0.0160(15) 0.4686(5) 0.077(3) Uani 1 1 d . . . . . H2 H 0.948527 -0.107055 0.500323 0.093 Uiso 1 1 calc R U . . . C3 C 0.9359(6) 0.0424(13) 0.4018(5) 0.073(3) Uani 1 1 d . . . . . H3 H 0.966971 -0.060652 0.387892 0.087 Uiso 1 1 calc R U . . . C4 C 0.8995(6) 0.2281(12) 0.3549(4) 0.056(2) Uani 1 1 d . . . . . O5 O 0.9122(4) 0.2499(8) 0.2890(3) 0.0641(16) Uani 1 1 d . . . . . C6 C 0.8808(6) 0.4318(13) 0.2411(4) 0.057(2) Uani 1 1 d . . . . . C7 C 0.8377(5) 0.5906(12) 0.2586(4) 0.053(2) Uani 1 1 d . . . . . O7 O 0.8105(4) 0.7736(10) 0.2100(4) 0.0646(16) Uani 1 1 d D . . . . H7 H 0.776(5) 0.832(15) 0.218(5) 0.078 Uiso 1 1 d D U . . . C8 C 0.8152(6) 0.5739(13) 0.3225(4) 0.058(2) Uani 1 1 d . . . . . O8 O 0.7688(4) 0.7103(9) 0.3343(3) 0.0736(17) Uani 1 1 d . . . . . C9 C 0.8524(5) 0.3835(13) 0.3740(5) 0.057(2) Uani 1 1 d . . . . . C10 C 0.8408(6) 0.3505(14) 0.4430(5) 0.065(2) Uani 1 1 d . . . . . H10 H 0.808151 0.449245 0.456605 0.078 Uiso 1 1 calc R U . . . C11 C 0.9009(6) 0.4218(14) 0.1717(4) 0.057(2) Uani 1 1 d . . . . . H11 H 0.872513 0.547562 0.137425 0.069 Uiso 1 1 calc R U . . . C12 C 0.8642(6) 0.2056(12) 0.1266(5) 0.065(2) Uani 1 1 d . . . . . H12A H 0.891696 0.079497 0.159883 0.078 Uiso 1 1 calc R U . . . H12B H 0.804165 0.198052 0.114381 0.078 Uiso 1 1 calc R U . . . O14 O 0.8721(6) 0.3371(16) 0.0110(4) 0.129(3) Uani 1 1 d . . . . . C13 C 0.8750(7) 0.1873(17) 0.0534(5) 0.079(3) Uani 1 1 d . . . . . O15 O 0.8878(5) -0.0217(12) 0.0388(4) 0.102(2) Uani 1 1 d . . . . . C16 C 0.8954(10) -0.065(2) -0.0337(7) 0.154(6) Uani 1 1 d . . . . . H16A H 0.846660 -0.006215 -0.076832 0.231 Uiso 1 1 calc R U . . . H16B H 0.898840 -0.222799 -0.040312 0.231 Uiso 1 1 calc R U . . . H16C H 0.945725 0.005560 -0.031935 0.231 Uiso 1 1 calc R U . . . C21 C 0.9958(6) 0.4449(14) 0.1963(5) 0.062(2) Uani 1 1 d . . . . . C22 C 1.0286(7) 0.6453(18) 0.1868(6) 0.091(3) Uani 1 1 d . . . . . H22 H 0.991931 0.764463 0.164967 0.109 Uiso 1 1 calc R U . . . C23 C 1.1134(9) 0.674(2) 0.2084(8) 0.113(4) Uani 1 1 d . . . . . H23 H 1.133436 0.807598 0.197389 0.135 Uiso 1 1 calc R U . . . C24 C 1.1694(9) 0.505(3) 0.2466(8) 0.117(5) Uani 1 1 d . . . . . H24 H 1.227586 0.527925 0.266152 0.140 Uiso 1 1 calc R U . . . C25 C 1.1381(9) 0.305(3) 0.2552(7) 0.117(4) Uani 1 1 d . . . . . H25 H 1.175003 0.185800 0.277089 0.140 Uiso 1 1 calc R U . . . C26 C 1.0528(8) 0.276(2) 0.2321(7) 0.096(3) Uani 1 1 d . . . . . H26 H 1.032848 0.139088 0.240622 0.115 Uiso 1 1 calc R U . . . Br2 Br 0.63966(8) 0.80185(18) -0.00810(6) 0.1019(4) Uani 1 1 d . . . . . C31 C 0.6062(6) 0.7021(14) 0.0695(5) 0.067(3) Uani 1 1 d . . . . . C32 C 0.5460(6) 0.8270(15) 0.0833(5) 0.074(2) Uani 1 1 d . . . . . H32 H 0.523781 0.956810 0.055078 0.088 Uiso 1 1 calc R U . . . C33 C 0.5201(6) 0.7572(14) 0.1381(5) 0.073(3) Uani 1 1 d . . . . . H33 H 0.479829 0.838587 0.147432 0.088 Uiso 1 1 calc R U . . . C34 C 0.5542(6) 0.5632(13) 0.1805(5) 0.063(2) Uani 1 1 d . . . . . O35 O 0.5267(4) 0.5013(9) 0.2350(3) 0.0669(16) Uani 1 1 d . . . . . C36 C 0.5590(5) 0.3169(15) 0.2795(5) 0.064(2) Uani 1 1 d . . . . . C37 C 0.6198(6) 0.1893(13) 0.2723(5) 0.063(2) Uani 1 1 d . . . . . O37 O 0.6497(5) 0.0121(10) 0.3202(4) 0.080(2) Uani 1 1 d D . . . . H37 H 0.685(6) -0.054(16) 0.311(6) 0.096 Uiso 1 1 d D U . . . C38 C 0.6506(6) 0.2408(12) 0.2143(5) 0.057(2) Uani 1 1 d . . . . . O38 O 0.7074(4) 0.1240(9) 0.2086(3) 0.0626(14) Uani 1 1 d . . . . . C39 C 0.6146(5) 0.4389(13) 0.1681(5) 0.056(2) Uani 1 1 d . . . . . C40 C 0.6397(6) 0.5084(14) 0.1101(5) 0.063(2) Uani 1 1 d . . . . . H40 H 0.678421 0.424793 0.099181 0.075 Uiso 1 1 calc R U . . . C41 C 0.5230(6) 0.2727(15) 0.3377(5) 0.073(3) Uani 1 1 d . . . . . H41 H 0.525249 0.110988 0.345832 0.088 Uiso 1 1 calc R U . . . C42 C 0.4305(6) 0.340(2) 0.3079(6) 0.096(3) Uani 1 1 d . . . . . H42A H 0.411827 0.312494 0.348776 0.115 Uiso 1 1 calc R U . . . H42B H 0.426056 0.499341 0.297707 0.115 Uiso 1 1 calc R U . . . C43 C 0.3735(10) 0.224(3) 0.2371(10) 0.157(8) Uani 1 1 d D U . . . O44 O 0.3338(14) 0.365(3) 0.1812(14) 0.182(9) Uani 0.6 1 d D . P A 1 O45 O 0.3589(14) 0.028(3) 0.229(2) 0.168(9) Uani 0.6 1 d D . P A 1 C46 C 0.3056(17) -0.080(4) 0.1596(15) 0.127(8) Uani 0.6 1 d D . P A 1 H46A H 0.255587 0.008475 0.132748 0.191 Uiso 0.6 1 calc R U P A 1 H46B H 0.289772 -0.223534 0.171499 0.191 Uiso 0.6 1 calc R U P A 1 H46C H 0.335084 -0.097723 0.127032 0.191 Uiso 0.6 1 calc R U P A 1 O47 O 0.400(2) 0.035(5) 0.241(3) 0.168(9) Uani 0.4 1 d D . P A 2 O48 O 0.3074(19) 0.262(5) 0.179(2) 0.182(9) Uani 0.4 1 d D . P A 2 C49 C 0.269(3) 0.036(5) 0.151(3) 0.127(8) Uani 0.4 1 d D . P A 2 H49A H 0.223249 0.050082 0.099421 0.191 Uiso 0.4 1 calc R U P A 2 H49B H 0.247166 -0.022637 0.185930 0.191 Uiso 0.4 1 calc R U P A 2 H49C H 0.311179 -0.062579 0.148668 0.191 Uiso 0.4 1 calc R U P A 2 C51 C 0.5757(6) 0.3771(15) 0.4164(6) 0.073(3) Uani 1 1 d . . . . . C52 C 0.6180(7) 0.577(2) 0.4238(7) 0.095(4) Uani 1 1 d . . . . . H52 H 0.616007 0.649033 0.379450 0.114 Uiso 1 1 calc R U . . . C53 C 0.6626(8) 0.669(3) 0.4954(10) 0.124(5) Uani 1 1 d . . . . . H53 H 0.689405 0.805529 0.499498 0.149 Uiso 1 1 calc R U . . . C54 C 0.6683(10) 0.562(4) 0.5616(10) 0.145(7) Uani 1 1 d . . . . . H54 H 0.701596 0.623076 0.610391 0.174 Uiso 1 1 calc R U . . . C55 C 0.6257(12) 0.368(4) 0.5565(9) 0.162(7) Uani 1 1 d . . . . . H55 H 0.627204 0.299645 0.601225 0.194 Uiso 1 1 calc R U . . . C56 C 0.5800(8) 0.275(2) 0.4834(8) 0.114(4) Uani 1 1 d . . . . . H56 H 0.551598 0.141025 0.479501 0.136 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1257(11) 0.1482(11) 0.0789(7) 0.0437(7) 0.0496(8) 0.0002(9) C1 0.070(7) 0.077(7) 0.071(6) 0.030(5) 0.022(6) 0.001(5) C2 0.087(8) 0.065(6) 0.058(6) 0.020(4) 0.011(6) 0.003(5) C3 0.087(8) 0.045(5) 0.058(6) 0.005(4) 0.005(5) 0.008(4) C4 0.063(6) 0.052(5) 0.043(5) 0.001(4) 0.013(4) -0.008(4) O5 0.083(4) 0.054(4) 0.055(4) 0.008(3) 0.029(3) 0.016(3) C6 0.076(6) 0.046(5) 0.044(5) 0.005(4) 0.022(5) 0.001(4) C7 0.068(6) 0.042(4) 0.048(5) 0.006(3) 0.024(4) -0.001(4) O7 0.080(5) 0.051(4) 0.073(4) 0.014(3) 0.043(4) 0.010(3) C8 0.071(6) 0.050(5) 0.055(5) 0.004(4) 0.028(5) -0.001(4) O8 0.088(5) 0.071(4) 0.076(4) 0.013(3) 0.050(4) 0.017(3) C9 0.061(6) 0.050(5) 0.052(5) 0.005(4) 0.016(5) -0.001(4) C10 0.070(6) 0.070(6) 0.054(5) 0.009(4) 0.025(5) -0.002(5) C11 0.067(6) 0.055(5) 0.049(5) 0.000(4) 0.024(5) 0.004(4) C12 0.080(7) 0.058(5) 0.057(6) 0.001(4) 0.028(5) 0.003(4) O14 0.227(10) 0.094(6) 0.072(5) 0.014(4) 0.068(6) 0.011(6) C13 0.109(9) 0.067(7) 0.055(6) -0.003(5) 0.030(6) -0.003(5) O15 0.161(8) 0.083(5) 0.075(5) -0.008(3) 0.061(5) 0.016(4) C16 0.252(19) 0.151(12) 0.102(10) -0.021(8) 0.118(12) 0.014(12) C21 0.076(7) 0.062(6) 0.055(5) -0.005(4) 0.036(5) 0.005(5) C22 0.102(9) 0.074(7) 0.126(9) -0.004(6) 0.077(8) 0.000(6) C23 0.107(11) 0.107(10) 0.157(12) -0.041(9) 0.088(11) -0.034(9) C24 0.085(10) 0.152(13) 0.117(11) -0.048(10) 0.047(9) 0.000(10) C25 0.083(10) 0.138(12) 0.102(9) -0.030(9) 0.013(8) 0.024(10) C26 0.086(9) 0.086(7) 0.115(9) 0.004(7) 0.043(7) 0.018(7) Br2 0.1201(10) 0.1029(8) 0.0861(8) 0.0314(6) 0.0471(7) 0.0065(8) C31 0.070(7) 0.061(6) 0.057(6) 0.006(4) 0.015(5) 0.000(5) C32 0.081(7) 0.055(5) 0.075(6) 0.002(5) 0.023(6) 0.010(5) C33 0.074(7) 0.059(6) 0.079(6) 0.003(5) 0.025(6) 0.013(5) C34 0.066(6) 0.052(5) 0.079(6) 0.002(4) 0.039(5) 0.002(4) O35 0.068(4) 0.058(3) 0.080(4) 0.001(3) 0.037(4) 0.010(3) C36 0.068(6) 0.052(5) 0.079(6) -0.003(5) 0.039(5) 0.002(5) C37 0.067(6) 0.052(5) 0.077(6) 0.002(4) 0.036(5) -0.003(4) O37 0.097(6) 0.067(4) 0.099(5) 0.024(3) 0.063(4) 0.024(3) C38 0.057(6) 0.052(5) 0.061(5) -0.004(4) 0.025(5) 0.000(4) O38 0.068(4) 0.054(3) 0.073(4) 0.009(3) 0.036(3) 0.006(3) C39 0.061(6) 0.049(5) 0.057(5) 0.000(4) 0.025(5) 0.003(4) C40 0.064(6) 0.059(5) 0.065(6) -0.004(4) 0.027(5) -0.004(4) C41 0.083(7) 0.066(6) 0.090(7) -0.006(5) 0.055(6) -0.005(5) C42 0.069(7) 0.143(10) 0.082(7) -0.027(7) 0.037(6) -0.023(7) C43 0.115(13) 0.25(2) 0.129(13) -0.037(14) 0.070(11) -0.014(13) O44 0.106(16) 0.18(2) 0.222(16) -0.114(17) 0.031(12) -0.049(12) O45 0.17(2) 0.153(10) 0.139(15) -0.049(9) 0.02(2) -0.116(13) C46 0.16(2) 0.081(17) 0.147(15) -0.038(16) 0.073(18) -0.031(14) O47 0.17(2) 0.153(10) 0.139(15) -0.049(9) 0.02(2) -0.116(13) O48 0.106(16) 0.18(2) 0.222(16) -0.114(17) 0.031(12) -0.049(12) C49 0.16(2) 0.081(17) 0.147(15) -0.038(16) 0.073(18) -0.031(14) C51 0.073(7) 0.080(7) 0.074(7) 0.000(5) 0.040(6) 0.011(5) C52 0.092(9) 0.099(9) 0.100(9) -0.021(7) 0.046(7) -0.022(7) C53 0.090(10) 0.141(12) 0.141(13) -0.047(11) 0.047(10) -0.013(9) C54 0.093(12) 0.22(2) 0.099(12) -0.063(14) 0.013(10) 0.009(12) C55 0.157(17) 0.25(2) 0.071(10) 0.023(12) 0.042(11) 0.033(15) C56 0.133(11) 0.113(9) 0.107(10) 0.013(8) 0.062(9) 0.006(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' O O 0.0106 0.0060 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 120.8(8) . . ? C2 C1 Br1 119.4(7) . . ? C10 C1 Br1 119.7(8) . . ? C3 C2 C1 121.3(8) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 118.4(9) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? O5 C4 C9 121.1(7) . . ? O5 C4 C3 116.9(8) . . ? C9 C4 C3 122.0(8) . . ? C4 O5 C6 120.4(6) . . ? C7 C6 O5 120.7(7) . . ? C7 C6 C11 127.5(7) . . ? O5 C6 C11 111.8(7) . . ? C6 C7 O7 118.3(6) . . ? C6 C7 C8 122.9(7) . . ? O7 C7 C8 118.7(7) . . ? C7 O7 H7 108(7) . . ? O8 C8 C7 122.9(7) . . ? O8 C8 C9 122.5(7) . . ? C7 C8 C9 114.6(8) . . ? C4 C9 C10 118.4(7) . . ? C4 C9 C8 119.8(7) . . ? C10 C9 C8 121.8(8) . . ? C1 C10 C9 118.9(9) . . ? C1 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C6 C11 C21 110.8(7) . . ? C6 C11 C12 108.9(7) . . ? C21 C11 C12 112.9(7) . . ? C6 C11 H11 108.0 . . ? C21 C11 H11 108.0 . . ? C12 C11 H11 108.0 . . ? C13 C12 C11 113.2(7) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.8 . . ? O14 C13 O15 122.6(9) . . ? O14 C13 C12 126.0(9) . . ? O15 C13 C12 111.4(8) . . ? C13 O15 C16 117.1(9) . . ? O15 C16 H16A 109.5 . . ? O15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C21 C26 117.1(10) . . ? C22 C21 C11 119.8(8) . . ? C26 C21 C11 123.0(9) . . ? C23 C22 C21 121.9(11) . . ? C23 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C22 C23 C24 119.7(13) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C25 C24 C23 119.0(14) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 120.6(13) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 121.4(12) . . ? C25 C26 H26 119.3 . . ? C21 C26 H26 119.3 . . ? C40 C31 C32 121.4(8) . . ? C40 C31 Br2 120.2(7) . . ? C32 C31 Br2 118.4(7) . . ? C33 C32 C31 119.5(8) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C32 C33 C34 119.8(9) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? O35 C34 C33 117.5(8) . . ? O35 C34 C39 121.1(7) . . ? C33 C34 C39 121.4(8) . . ? C34 O35 C36 120.3(6) . . ? C37 C36 O35 122.2(7) . . ? C37 C36 C41 123.9(8) . . ? O35 C36 C41 113.9(7) . . ? O37 C37 C36 118.2(7) . . ? O37 C37 C38 121.1(8) . . ? C36 C37 C38 120.7(8) . . ? C37 O37 H37 111(7) . . ? O38 C38 C39 124.2(7) . . ? O38 C38 C37 120.4(7) . . ? C39 C38 C37 115.4(8) . . ? C34 C39 C40 118.7(7) . . ? C34 C39 C38 120.3(7) . . ? C40 C39 C38 121.0(8) . . ? C31 C40 C39 119.1(8) . . ? C31 C40 H40 120.4 . . ? C39 C40 H40 120.4 . . ? C36 C41 C51 112.3(8) . . ? C36 C41 C42 112.8(8) . . ? C51 C41 C42 111.1(8) . . ? C36 C41 H41 106.8 . . ? C51 C41 H41 106.8 . . ? C42 C41 H41 106.8 . . ? C43 C42 C41 114.5(10) . . ? C43 C42 H42A 108.6 . . ? C41 C42 H42A 108.6 . . ? C43 C42 H42B 108.6 . . ? C41 C42 H42B 108.6 . . ? H42A C42 H42B 107.6 . . ? O48 C43 O47 114(3) . . ? O45 C43 O44 122(2) . . ? O48 C43 C42 138(2) . . ? O45 C43 C42 127(2) . . ? O47 C43 C42 107(3) . . ? O44 C43 C42 111.0(18) . . ? C43 O45 C46 126(3) . . ? O45 C46 H46A 109.5 . . ? O45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? O45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C43 O48 C49 105(3) . . ? O48 C49 H49A 109.5 . . ? O48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? O48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C56 C51 C52 118.2(10) . . ? C56 C51 C41 119.6(10) . . ? C52 C51 C41 122.2(9) . . ? C53 C52 C51 120.5(12) . . ? C53 C52 H52 119.8 . . ? C51 C52 H52 119.8 . . ? C54 C53 C52 120.7(15) . . ? C54 C53 H53 119.7 . . ? C52 C53 H53 119.7 . . ? C55 C54 C53 120.5(16) . . ? C55 C54 H54 119.8 . . ? C53 C54 H54 119.8 . . ? C54 C55 C56 118.8(16) . . ? C54 C55 H55 120.6 . . ? C56 C55 H55 120.6 . . ? C51 C56 C55 121.4(14) . . ? C51 C56 H56 119.3 . . ? C55 C56 H56 119.3 . . ? 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 C1 1.876(9) . ? C1 C2 1.379(13) . ? C1 C10 1.389(12) . ? C2 C3 1.363(12) . ? C2 H2 0.9300 . ? C3 C4 1.397(10) . ? C3 H3 0.9300 . ? C4 O5 1.359(9) . ? C4 C9 1.386(11) . ? O5 C6 1.374(9) . ? C6 C7 1.337(11) . ? C6 C11 1.494(11) . ? C7 O7 1.380(9) . ? C7 C8 1.422(11) . ? O7 H7 0.76(6) . ? C8 O8 1.234(9) . ? C8 C9 1.461(11) . ? C9 C10 1.414(11) . ? C10 H10 0.9300 . ? C11 C21 1.521(12) . ? C11 C12 1.534(11) . ? C11 H11 0.9800 . ? C12 C13 1.478(12) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? O14 C13 1.190(12) . ? C13 O15 1.323(11) . ? O15 C16 1.454(11) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C21 C22 1.374(13) . ? C21 C26 1.380(13) . ? C22 C23 1.367(15) . ? C22 H22 0.9300 . ? C23 C24 1.380(17) . ? C23 H23 0.9300 . ? C24 C25 1.358(18) . ? C24 H24 0.9300 . ? C25 C26 1.370(15) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? Br2 C31 1.888(9) . ? C31 C40 1.378(11) . ? C31 C32 1.400(12) . ? C32 C33 1.359(12) . ? C32 H32 0.9300 . ? C33 C34 1.394(11) . ? C33 H33 0.9300 . ? C34 O35 1.358(9) . ? C34 C39 1.387(11) . ? O35 C36 1.359(10) . ? C36 C37 1.359(11) . ? C36 C41 1.502(11) . ? C37 O37 1.349(10) . ? C37 C38 1.442(11) . ? O37 H37 0.81(6) . ? C38 O38 1.253(9) . ? C38 C39 1.450(11) . ? C39 C40 1.404(11) . ? C40 H40 0.9300 . ? C41 C51 1.513(12) . ? C41 C42 1.518(13) . ? C41 H41 0.9800 . ? C42 C43 1.46(2) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 O48 1.23(2) . ? C43 O45 1.20(2) . ? C43 O47 1.22(3) . ? C43 O44 1.30(2) . ? O45 C46 1.41(3) . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? O48 C49 1.50(3) . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C51 C56 1.379(14) . ? C51 C52 1.384(14) . ? C52 C53 1.359(16) . ? C52 H52 0.9300 . ? C53 C54 1.37(2) . ? C53 H53 0.9300 . ? C54 C55 1.36(2) . ? C54 H54 0.9300 . ? C55 C56 1.39(2) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? 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 C10 C1 C2 C3 1.8(15) . . . . ? Br1 C1 C2 C3 -178.8(7) . . . . ? C1 C2 C3 C4 -0.2(14) . . . . ? C2 C3 C4 O5 179.7(8) . . . . ? C2 C3 C4 C9 -0.5(13) . . . . ? C9 C4 O5 C6 2.3(11) . . . . ? C3 C4 O5 C6 -177.8(7) . . . . ? C4 O5 C6 C7 0.3(12) . . . . ? C4 O5 C6 C11 -179.3(7) . . . . ? O5 C6 C7 O7 177.6(7) . . . . ? C11 C6 C7 O7 -2.8(13) . . . . ? O5 C6 C7 C8 -5.6(13) . . . . ? C11 C6 C7 C8 173.9(8) . . . . ? C6 C7 C8 O8 -173.1(8) . . . . ? O7 C7 C8 O8 3.7(12) . . . . ? C6 C7 C8 C9 7.7(12) . . . . ? O7 C7 C8 C9 -175.5(7) . . . . ? O5 C4 C9 C10 179.5(8) . . . . ? C3 C4 C9 C10 -0.4(12) . . . . ? O5 C4 C9 C8 0.3(12) . . . . ? C3 C4 C9 C8 -179.6(8) . . . . ? O8 C8 C9 C4 175.9(8) . . . . ? C7 C8 C9 C4 -5.0(11) . . . . ? O8 C8 C9 C10 -3.3(13) . . . . ? C7 C8 C9 C10 175.9(7) . . . . ? C2 C1 C10 C9 -2.7(14) . . . . ? Br1 C1 C10 C9 178.0(7) . . . . ? C4 C9 C10 C1 1.9(12) . . . . ? C8 C9 C10 C1 -178.9(8) . . . . ? C7 C6 C11 C21 113.3(10) . . . . ? O5 C6 C11 C21 -67.1(9) . . . . ? C7 C6 C11 C12 -121.9(10) . . . . ? O5 C6 C11 C12 57.7(9) . . . . ? C6 C11 C12 C13 175.7(8) . . . . ? C21 C11 C12 C13 -60.8(10) . . . . ? C11 C12 C13 O14 -35.2(17) . . . . ? C11 C12 C13 O15 145.6(9) . . . . ? O14 C13 O15 C16 -2.2(18) . . . . ? C12 C13 O15 C16 177.1(10) . . . . ? C6 C11 C21 C22 -102.0(9) . . . . ? C12 C11 C21 C22 135.6(8) . . . . ? C6 C11 C21 C26 74.7(10) . . . . ? C12 C11 C21 C26 -47.8(11) . . . . ? C26 C21 C22 C23 2.8(15) . . . . ? C11 C21 C22 C23 179.7(9) . . . . ? C21 C22 C23 C24 -5.3(17) . . . . ? C22 C23 C24 C25 6.4(19) . . . . ? C23 C24 C25 C26 -5.2(19) . . . . ? C24 C25 C26 C21 2.9(18) . . . . ? C22 C21 C26 C25 -1.6(15) . . . . ? C11 C21 C26 C25 -178.3(9) . . . . ? C40 C31 C32 C33 0.4(14) . . . . ? Br2 C31 C32 C33 179.2(7) . . . . ? C31 C32 C33 C34 0.5(14) . . . . ? C32 C33 C34 O35 179.6(8) . . . . ? C32 C33 C34 C39 0.2(13) . . . . ? C33 C34 O35 C36 -178.4(8) . . . . ? C39 C34 O35 C36 1.0(12) . . . . ? C34 O35 C36 C37 0.7(12) . . . . ? C34 O35 C36 C41 179.2(7) . . . . ? O35 C36 C37 O37 178.4(8) . . . . ? C41 C36 C37 O37 0.1(13) . . . . ? O35 C36 C37 C38 -2.4(13) . . . . ? C41 C36 C37 C38 179.3(8) . . . . ? O37 C37 C38 O38 -1.6(13) . . . . ? C36 C37 C38 O38 179.2(8) . . . . ? O37 C37 C38 C39 -178.5(8) . . . . ? C36 C37 C38 C39 2.3(12) . . . . ? O35 C34 C39 C40 178.9(8) . . . . ? C33 C34 C39 C40 -1.7(13) . . . . ? O35 C34 C39 C38 -0.9(12) . . . . ? C33 C34 C39 C38 178.5(8) . . . . ? O38 C38 C39 C34 -177.5(8) . . . . ? C37 C38 C39 C34 -0.7(12) . . . . ? O38 C38 C39 C40 2.7(13) . . . . ? C37 C38 C39 C40 179.5(8) . . . . ? C32 C31 C40 C39 -1.9(13) . . . . ? Br2 C31 C40 C39 179.3(7) . . . . ? C34 C39 C40 C31 2.5(12) . . . . ? C38 C39 C40 C31 -177.6(8) . . . . ? C37 C36 C41 C51 86.0(11) . . . . ? O35 C36 C41 C51 -92.5(9) . . . . ? C37 C36 C41 C42 -147.6(9) . . . . ? O35 C36 C41 C42 33.9(11) . . . . ? C36 C41 C42 C43 60.4(14) . . . . ? C51 C41 C42 C43 -172.5(11) . . . . ? C41 C42 C43 O48 -148(3) . . . . ? C41 C42 C43 O45 63(3) . . . . ? C41 C42 C43 O47 35(3) . . . . ? C41 C42 C43 O44 -121.3(19) . . . . ? O44 C43 O45 C46 7(4) . . . . ? C42 C43 O45 C46 -178(2) . . . . ? O47 C43 O48 C49 21(5) . . . . ? C42 C43 O48 C49 -156(3) . . . . ? C36 C41 C51 C56 -148.5(10) . . . . ? C42 C41 C51 C56 84.2(11) . . . . ? C36 C41 C51 C52 33.7(13) . . . . ? C42 C41 C51 C52 -93.6(11) . . . . ? C56 C51 C52 C53 0.1(17) . . . . ? C41 C51 C52 C53 177.9(10) . . . . ? C51 C52 C53 C54 2(2) . . . . ? C52 C53 C54 C55 -4(3) . . . . ? C53 C54 C55 C56 3(3) . . . . ? C52 C51 C56 C55 -0.4(18) . . . . ? C41 C51 C56 C55 -178.3(13) . . . . ? C54 C55 C56 C51 -1(2) . . . . ?