#------------------------------------------------------------------------------ #$Date: 2021-04-08 06:43:49 +0300 (Thu, 08 Apr 2021) $ #$Revision: 263963 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158012.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_7158012 loop_ _publ_author_name 'Jin, Jiang' 'Li, Yinghua' 'Xiang, Shiqun' 'Fan, Weibin' 'Guo, Shiwei' 'Huang, Deguang' _publ_section_title ; Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl tert-butyl ether as a new methylene precursor ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB00120E _journal_year 2021 _chemical_formula_moiety 'C23 H22 Br2 O6' _chemical_formula_sum 'C23 H22 Br2 O6' _chemical_formula_weight 554.22 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-01-15 deposited with the CCDC. 2021-04-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.6128(9) _cell_length_b 12.3072(6) _cell_length_c 9.3607(5) _cell_measurement_reflns_used 3013 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 71.5710 _cell_measurement_theta_min 5.9170 _cell_volume 2259.47(19) _computing_cell_refinement 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 10.5594 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_unetI/netI 0.0366 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6485 _diffrn_reflns_point_group_measured_fraction_full 0.731 _diffrn_reflns_point_group_measured_fraction_max 0.723 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 69.994 _diffrn_reflns_theta_min 4.241 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 4.869 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.70698 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description block _exptl_crystal_F_000 1112 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.617 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.080 _refine_ls_abs_structure_details ; Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.06(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 3101 _refine_ls_number_restraints 487 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0380 _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^)+(0.0678P)^2^+0.9057P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1015 _refine_ls_wR_factor_ref 0.1054 _reflns_Friedel_coverage 0.362 _reflns_Friedel_fraction_full 0.424 _reflns_Friedel_fraction_max 0.411 _reflns_number_gt 2867 _reflns_number_total 3101 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00120e2.cif _cod_data_source_block Compound5g _cod_database_code 7158012 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.443 _shelx_estimated_absorpt_t_max 0.642 _shelx_res_file ; TITL full in Pna21 #33 full.res created by SHELXL-2018/3 at 21:46:44 on 18-Nov-2020 CELL 1.54184 19.61279 12.30721 9.3607 90 90 90 ZERR 4 0.00085 0.00057 0.00053 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,0.5+Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SFAC C H Br O UNIT 92 88 8 24 TEMP -123 SIZE 0.20 0.15 0.10 EADP C20 C20' EXYZ C20 C20' EADP C12 C12' EXYZ C12 C12' EADP C8 C8' EXYZ C8 C8' DELU 0.005 0.005 Br1 > C23' SIMU 0.005 0.005 Br1 > C23' OMIT 0 140 L.S. 6 PLAN 4 CONF BOND $H fmap 2 MORE -1 ACTA WGHT 0.067800 0.905700 FVAR 0.40800 0.74545 BR1 3 0.830333 -0.511158 -0.017576 11.00000 0.08001 0.03518 = 0.05977 -0.00570 0.00984 -0.02387 BR2 3 0.925570 0.590287 0.635284 11.00000 0.05507 0.04203 = 0.04238 -0.01134 -0.00250 -0.00296 O1 4 1.002960 -0.110202 0.333472 11.00000 0.03475 0.03925 = 0.03262 0.00395 -0.00488 -0.00015 O2 4 1.035092 0.152206 0.236899 11.00000 0.03013 0.04060 = 0.05778 -0.00634 -0.00352 -0.00549 O3 4 1.082244 0.019693 0.105661 11.00000 0.02276 0.04321 = 0.04344 0.00607 0.00266 -0.00011 O4 4 0.770437 0.213919 0.203446 11.00000 0.02602 0.04589 = 0.05669 -0.00649 -0.00823 0.00314 C1 1 0.895690 -0.194626 0.037873 11.00000 0.03618 0.02696 = 0.03920 0.00311 -0.00108 -0.00124 AFIX 43 H1A 2 0.890312 -0.127124 -0.010044 11.00000 -1.20000 AFIX 0 C2 1 0.864178 -0.287232 -0.017098 11.00000 0.04264 0.03110 = 0.03727 0.00062 -0.00180 -0.00309 AFIX 43 H2A 2 0.838316 -0.283681 -0.102782 11.00000 -1.20000 AFIX 0 C3 1 0.871338 -0.383883 0.055408 11.00000 0.04787 0.02702 = 0.04188 -0.00347 0.00728 -0.00714 C4 1 0.910068 -0.391449 0.178157 11.00000 0.04712 0.02794 = 0.03687 0.00462 0.01029 0.00144 AFIX 43 H4A 2 0.915288 -0.459331 0.225219 11.00000 -1.20000 AFIX 0 C5 1 0.941270 -0.299091 0.232112 11.00000 0.03605 0.02940 = 0.03613 0.00521 0.00219 0.00369 AFIX 43 H5A 2 0.967215 -0.303524 0.317615 11.00000 -1.20000 AFIX 0 C6 1 0.934831 -0.199367 0.161552 11.00000 0.02793 0.02438 = 0.03190 0.00147 0.00333 0.00153 C7 1 0.970383 -0.103471 0.221574 11.00000 0.02331 0.02779 = 0.03357 0.00366 0.00152 0.00229 C9 1 1.030157 0.069001 0.169871 11.00000 0.02480 0.03291 = 0.03967 0.00463 -0.00042 -0.00119 C10 1 1.148265 0.072297 0.119675 11.00000 0.02511 0.05201 = 0.04326 0.00869 0.00181 -0.00447 AFIX 23 H10A 2 1.184437 0.016307 0.124426 11.00000 -1.20000 H10B 2 1.149506 0.114505 0.209670 11.00000 -1.20000 AFIX 0 C11 1 1.161721 0.146085 -0.003055 11.00000 0.03340 0.03960 = 0.04601 0.00561 -0.00566 -0.00761 AFIX 33 H11A 2 1.206432 0.180438 0.008968 11.00000 -1.50000 H11B 2 1.161243 0.104161 -0.092056 11.00000 -1.50000 H11C 2 1.126350 0.202252 -0.006905 11.00000 -1.50000 AFIX 0 C13 1 0.923132 0.327571 0.361042 11.00000 0.03017 0.03035 = 0.03454 0.00143 -0.00157 0.00507 AFIX 43 H13A 2 0.955985 0.279604 0.321240 11.00000 -1.20000 AFIX 0 C14 1 0.943532 0.407039 0.456710 11.00000 0.03143 0.03549 = 0.03490 -0.00038 -0.00386 0.00082 AFIX 43 H14A 2 0.990180 0.413101 0.482859 11.00000 -1.20000 AFIX 0 C15 1 0.895991 0.477513 0.514113 11.00000 0.03970 0.03118 = 0.03530 -0.00114 -0.00027 0.00007 C16 1 0.826798 0.469391 0.478469 11.00000 0.03489 0.03468 = 0.04324 -0.00077 0.00232 0.00297 AFIX 43 H16A 2 0.794304 0.517924 0.518382 11.00000 -1.20000 AFIX 0 C17 1 0.806763 0.388712 0.383377 11.00000 0.02900 0.03376 = 0.04080 0.00067 0.00035 0.00250 AFIX 43 H17A 2 0.759952 0.381625 0.359018 11.00000 -1.20000 AFIX 0 C18 1 0.854713 0.317470 0.322729 11.00000 0.02834 0.02788 = 0.03537 0.00013 -0.00166 0.00117 C19 1 0.830330 0.233951 0.218339 11.00000 0.02950 0.03038 = 0.03572 0.00194 -0.00384 0.00257 PART 1 O5 4 0.840336 0.061073 -0.062850 21.00000 0.03420 0.02418 = 0.03438 0.00486 -0.00451 -0.00366 O6 4 0.862354 0.239089 -0.098456 21.00000 0.04169 0.02505 = 0.03179 0.00512 -0.00355 0.00294 C8 1 0.964031 0.006308 0.147105 21.00000 0.02433 0.02690 = 0.03338 0.00213 -0.00076 -0.00009 AFIX 13 H8A 2 0.956336 -0.005033 0.042557 21.00000 -1.20000 AFIX 0 C12 1 0.902288 0.066757 0.212462 21.00000 0.02527 0.02533 = 0.03134 0.00281 -0.00235 -0.00029 AFIX 23 H12A 2 0.862365 0.017532 0.212505 21.00000 -1.20000 H12B 2 0.912747 0.085371 0.312992 21.00000 -1.20000 AFIX 0 C20 1 0.883779 0.170987 0.131565 21.00000 0.02961 0.02545 = 0.03194 0.00410 -0.00344 0.00098 AFIX 13 H20A 2 0.925725 0.216928 0.125248 21.00000 -1.20000 AFIX 0 C21 1 0.859097 0.148688 -0.020283 21.00000 0.03358 0.02538 = 0.03361 0.00502 -0.00406 0.00030 C22 1 0.848709 0.225894 -0.249856 21.00000 0.04188 0.03337 = 0.03236 0.00283 -0.00122 0.00254 AFIX 23 H22A 2 0.868430 0.156292 -0.283078 21.00000 -1.20000 H22B 2 0.870963 0.285443 -0.303538 21.00000 -1.20000 AFIX 0 C23 1 0.774180 0.226863 -0.279781 21.00000 0.04283 0.04571 = 0.04028 0.00331 -0.00262 0.00462 AFIX 33 H23A 2 0.766576 0.217822 -0.382569 21.00000 -1.50000 H23B 2 0.752181 0.167184 -0.228018 21.00000 -1.50000 H23C 2 0.754711 0.296220 -0.248459 21.00000 -1.50000 AFIX 0 PART 2 O5' 4 0.829114 0.042896 -0.037638 -21.00000 0.03456 0.02660 = 0.03322 0.00384 -0.00368 -0.00040 O6' 4 0.821906 0.229813 -0.078995 -21.00000 0.03918 0.02764 = 0.03256 0.00536 -0.00469 0.00251 C8' 1 0.964031 0.006308 0.147105 -21.00000 0.02433 0.02690 = 0.03338 0.00213 -0.00076 -0.00009 AFIX 13 H8'A 2 0.956336 -0.005033 0.042557 -21.00000 -1.20000 AFIX 0 C12' 1 0.902288 0.066757 0.212462 -21.00000 0.02527 0.02533 = 0.03134 0.00281 -0.00235 -0.00029 AFIX 23 H12C 2 0.862365 0.017532 0.212505 -21.00000 -1.20000 H12D 2 0.912747 0.085371 0.312992 -21.00000 -1.20000 AFIX 0 C20' 1 0.883779 0.170987 0.131565 -21.00000 0.02961 0.02545 = 0.03194 0.00410 -0.00344 0.00098 AFIX 13 H20B 2 0.924712 0.216153 0.108528 -21.00000 -1.20000 AFIX 0 C21' 1 0.842669 0.139489 -0.003349 -21.00000 0.03473 0.02614 = 0.03277 0.00476 -0.00369 0.00018 C22' 1 0.789904 0.209464 -0.207973 -21.00000 0.04151 0.03415 = 0.03334 0.00453 -0.00299 0.00331 AFIX 23 H22C 2 0.754174 0.265017 -0.223656 -21.00000 -1.20000 H22D 2 0.767251 0.137672 -0.203169 -21.00000 -1.20000 AFIX 0 C23' 1 0.836535 0.210430 -0.328263 -21.00000 0.04308 0.03982 = 0.03592 0.00479 -0.00138 0.00304 AFIX 33 H23D 2 0.811256 0.195630 -0.416449 -21.00000 -1.50000 H23E 2 0.858384 0.281855 -0.335050 -21.00000 -1.50000 H23F 2 0.871467 0.154456 -0.314554 -21.00000 -1.50000 PART 0 AFIX 0 HKLF 4 REM full in Pna21 #33 REM wR2 = 0.1054, GooF = S = 1.047, Restrained GooF = 1.013 for all data REM R1 = 0.0380 for 2867 Fo > 4sig(Fo) and 0.0421 for all 3101 data REM 326 parameters refined using 487 restraints END WGHT 0.0676 0.8946 REM Highest difference peak 0.617, deepest hole -0.559, 1-sigma level 0.080 Q1 1 0.8729 -0.5167 -0.0115 11.00000 0.05 0.62 Q2 1 0.8807 0.5797 0.6280 11.00000 0.05 0.54 Q3 1 0.8154 -0.5071 -0.1025 11.00000 0.05 0.36 Q4 1 0.8749 0.4764 0.4988 11.00000 0.05 0.32 ; _shelx_res_checksum 30642 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -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 0.83033(4) -0.51116(5) -0.01758(11) 0.0583(2) Uani 1 1 d . U . . . Br2 Br 0.92557(3) 0.59029(5) 0.63528(8) 0.0465(2) Uani 1 1 d . U . . . O1 O 1.0030(2) -0.1102(3) 0.3335(5) 0.0355(8) Uani 1 1 d . U . . . O2 O 1.0351(2) 0.1522(4) 0.2369(5) 0.0428(10) Uani 1 1 d . U . . . O3 O 1.08224(18) 0.0197(4) 0.1057(5) 0.0365(9) Uani 1 1 d . U . . . O4 O 0.7704(2) 0.2139(4) 0.2034(6) 0.0429(10) Uani 1 1 d . U . . . C1 C 0.8957(3) -0.1946(5) 0.0379(7) 0.0341(11) Uani 1 1 d . U . . . H1A H 0.890312 -0.127124 -0.010044 0.041 Uiso 1 1 calc R U . . . C2 C 0.8642(3) -0.2872(4) -0.0171(8) 0.0370(11) Uani 1 1 d . U . . . H2A H 0.838316 -0.283681 -0.102782 0.044 Uiso 1 1 calc R U . . . C3 C 0.8713(3) -0.3839(5) 0.0554(7) 0.0389(11) Uani 1 1 d . U . . . C4 C 0.9101(3) -0.3914(5) 0.1782(7) 0.0373(11) Uani 1 1 d . U . . . H4A H 0.915288 -0.459331 0.225219 0.045 Uiso 1 1 calc R U . . . C5 C 0.9413(3) -0.2991(5) 0.2321(7) 0.0339(11) Uani 1 1 d . U . . . H5A H 0.967215 -0.303524 0.317615 0.041 Uiso 1 1 calc R U . . . C6 C 0.9348(3) -0.1994(4) 0.1616(6) 0.0281(10) Uani 1 1 d . U . . . C7 C 0.9704(3) -0.1035(4) 0.2216(7) 0.0282(9) Uani 1 1 d . U . . . C9 C 1.0302(3) 0.0690(5) 0.1699(7) 0.0325(10) Uani 1 1 d . U . . . C10 C 1.1483(3) 0.0723(5) 0.1197(8) 0.0401(12) Uani 1 1 d . U . . . H10A H 1.184437 0.016307 0.124426 0.048 Uiso 1 1 calc R U . . . H10B H 1.149506 0.114505 0.209670 0.048 Uiso 1 1 calc R U . . . C11 C 1.1617(3) 0.1461(5) -0.0031(8) 0.0397(12) Uani 1 1 d . U . . . H11A H 1.206432 0.180438 0.008968 0.060 Uiso 1 1 calc R U . . . H11B H 1.161243 0.104161 -0.092056 0.060 Uiso 1 1 calc R U . . . H11C H 1.126350 0.202252 -0.006905 0.060 Uiso 1 1 calc R U . . . C13 C 0.9231(3) 0.3276(5) 0.3610(7) 0.0317(11) Uani 1 1 d . U . . . H13A H 0.955985 0.279604 0.321240 0.038 Uiso 1 1 calc R U . . . C14 C 0.9435(3) 0.4070(5) 0.4567(7) 0.0339(11) Uani 1 1 d . U . . . H14A H 0.990180 0.413101 0.482859 0.041 Uiso 1 1 calc R U . . . C15 C 0.8960(3) 0.4775(5) 0.5141(7) 0.0354(11) Uani 1 1 d . U . . . C16 C 0.8268(3) 0.4694(5) 0.4785(9) 0.0376(11) Uani 1 1 d . U . . . H16A H 0.794304 0.517924 0.518382 0.045 Uiso 1 1 calc R U . . . C17 C 0.8068(3) 0.3887(5) 0.3834(7) 0.0345(11) Uani 1 1 d . U . . . H17A H 0.759952 0.381625 0.359018 0.041 Uiso 1 1 calc R U . . . C18 C 0.8547(3) 0.3175(5) 0.3227(7) 0.0305(10) Uani 1 1 d . U . . . C19 C 0.8303(3) 0.2340(5) 0.2183(7) 0.0319(10) Uani 1 1 d . U . . . O5 O 0.8403(4) 0.0611(6) -0.0629(9) 0.0309(14) Uani 0.745(8) 1 d . U P A 1 O6 O 0.8624(3) 0.2391(4) -0.0985(6) 0.0328(11) Uani 0.745(8) 1 d . U P A 1 C8 C 0.9640(2) 0.0063(4) 0.1471(7) 0.0282(8) Uani 0.745(8) 1 d . U P A 1 H8A H 0.956336 -0.005033 0.042557 0.034 Uiso 0.745(8) 1 calc R U P A 1 C12 C 0.9023(3) 0.0668(4) 0.2125(6) 0.0273(8) Uani 0.745(8) 1 d . U P A 1 H12A H 0.862365 0.017532 0.212505 0.033 Uiso 0.745(8) 1 calc R U P A 1 H12B H 0.912747 0.085371 0.312992 0.033 Uiso 0.745(8) 1 calc R U P A 1 C20 C 0.8838(2) 0.1710(4) 0.1316(7) 0.0290(7) Uani 0.745(8) 1 d . U P A 1 H20A H 0.925725 0.216928 0.125248 0.035 Uiso 0.745(8) 1 calc R U P A 1 C21 C 0.8591(4) 0.1487(8) -0.0203(12) 0.0309(12) Uani 0.745(8) 1 d . U P A 1 C22 C 0.8487(5) 0.2259(7) -0.2499(10) 0.0359(13) Uani 0.745(8) 1 d . U P A 1 H22A H 0.868430 0.156292 -0.283078 0.043 Uiso 0.745(8) 1 calc R U P A 1 H22B H 0.870963 0.285443 -0.303538 0.043 Uiso 0.745(8) 1 calc R U P A 1 C23 C 0.7742(5) 0.2269(8) -0.2798(11) 0.0429(16) Uani 0.745(8) 1 d . U P A 1 H23A H 0.766576 0.217822 -0.382569 0.064 Uiso 0.745(8) 1 calc R U P A 1 H23B H 0.752181 0.167184 -0.228018 0.064 Uiso 0.745(8) 1 calc R U P A 1 H23C H 0.754711 0.296220 -0.248459 0.064 Uiso 0.745(8) 1 calc R U P A 1 O5' O 0.8291(14) 0.043(2) -0.038(3) 0.031(2) Uani 0.255(8) 1 d . U P A 2 O6' O 0.8219(10) 0.2298(13) -0.0790(19) 0.0331(15) Uani 0.255(8) 1 d . U P A 2 C8' C 0.9640(2) 0.0063(4) 0.1471(7) 0.0282(8) Uani 0.255(8) 1 d . U P A 2 H8'A H 0.956336 -0.005033 0.042557 0.034 Uiso 0.255(8) 1 calc R U P A 2 C12' C 0.9023(3) 0.0668(4) 0.2125(6) 0.0273(8) Uani 0.255(8) 1 d . U P A 2 H12C H 0.862365 0.017532 0.212505 0.033 Uiso 0.255(8) 1 calc R U P A 2 H12D H 0.912747 0.085371 0.312992 0.033 Uiso 0.255(8) 1 calc R U P A 2 C20' C 0.8838(2) 0.1710(4) 0.1316(7) 0.0290(7) Uani 0.255(8) 1 d . U P A 2 H20B H 0.924712 0.216153 0.108528 0.035 Uiso 0.255(8) 1 calc R U P A 2 C21' C 0.8427(14) 0.139(3) -0.003(4) 0.0312(14) Uani 0.255(8) 1 d . U P A 2 C22' C 0.7899(14) 0.209(2) -0.208(3) 0.0363(17) Uani 0.255(8) 1 d . U P A 2 H22C H 0.754174 0.265017 -0.223656 0.044 Uiso 0.255(8) 1 calc R U P A 2 H22D H 0.767251 0.137672 -0.203169 0.044 Uiso 0.255(8) 1 calc R U P A 2 C23' C 0.8365(14) 0.210(2) -0.328(3) 0.040(2) Uani 0.255(8) 1 d . U P A 2 H23D H 0.811256 0.195630 -0.416449 0.059 Uiso 0.255(8) 1 calc R U P A 2 H23E H 0.858384 0.281855 -0.335050 0.059 Uiso 0.255(8) 1 calc R U P A 2 H23F H 0.871467 0.154456 -0.314554 0.059 Uiso 0.255(8) 1 calc R U P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0800(5) 0.0352(3) 0.0598(5) -0.0057(4) 0.0098(5) -0.0239(3) Br2 0.0551(4) 0.0420(3) 0.0424(4) -0.0113(3) -0.0025(4) -0.0030(3) O1 0.0347(19) 0.039(2) 0.033(2) 0.0040(17) -0.0049(16) -0.0002(16) O2 0.0301(18) 0.041(2) 0.058(3) -0.0063(19) -0.0035(19) -0.0055(17) O3 0.0228(15) 0.043(2) 0.043(3) 0.0061(17) 0.0027(15) -0.0001(14) O4 0.0260(16) 0.046(2) 0.057(2) -0.006(2) -0.0082(18) 0.0031(16) C1 0.036(2) 0.027(2) 0.039(3) 0.003(2) -0.001(2) -0.0012(19) C2 0.043(3) 0.031(2) 0.037(3) 0.001(2) -0.002(2) -0.0031(19) C3 0.048(2) 0.027(2) 0.042(2) -0.003(2) 0.007(2) -0.007(2) C4 0.047(3) 0.028(2) 0.037(3) 0.005(2) 0.010(2) 0.001(2) C5 0.036(2) 0.029(2) 0.036(3) 0.005(2) 0.002(2) 0.004(2) C6 0.028(2) 0.0244(18) 0.032(2) 0.0015(18) 0.0033(18) 0.0015(16) C7 0.0233(19) 0.0278(18) 0.034(2) 0.0037(18) 0.0015(17) 0.0023(16) C9 0.0248(17) 0.033(2) 0.040(2) 0.0046(18) -0.0004(18) -0.0012(17) C10 0.025(2) 0.052(3) 0.043(3) 0.009(3) 0.002(2) -0.004(2) C11 0.033(2) 0.040(3) 0.046(3) 0.006(3) -0.006(2) -0.008(2) C13 0.030(2) 0.030(2) 0.035(3) 0.001(2) -0.002(2) 0.0051(19) C14 0.031(2) 0.035(2) 0.035(3) 0.000(2) -0.004(2) 0.0008(19) C15 0.040(2) 0.031(2) 0.035(3) -0.0011(19) 0.000(2) 0.0001(18) C16 0.035(2) 0.035(2) 0.043(3) -0.001(2) 0.002(2) 0.0030(19) C17 0.029(2) 0.034(2) 0.041(3) 0.001(2) 0.000(2) 0.003(2) C18 0.028(2) 0.028(2) 0.035(2) 0.0001(18) -0.0017(19) 0.0012(17) C19 0.0295(19) 0.030(2) 0.036(2) 0.0019(18) -0.0038(18) 0.0026(17) O5 0.034(3) 0.024(3) 0.034(3) 0.005(2) -0.005(2) -0.004(2) O6 0.042(3) 0.0250(19) 0.032(2) 0.0051(18) -0.004(2) 0.003(2) C8 0.0243(15) 0.0269(15) 0.0334(18) 0.0021(16) -0.0008(16) -0.0001(13) C12 0.0253(16) 0.0253(16) 0.0313(18) 0.0028(16) -0.0023(16) -0.0003(14) C20 0.0296(15) 0.0254(15) 0.0319(16) 0.0041(15) -0.0034(16) 0.0010(14) C21 0.034(3) 0.025(2) 0.034(2) 0.005(2) -0.004(2) 0.000(2) C22 0.042(3) 0.033(3) 0.032(3) 0.003(3) -0.001(3) 0.003(2) C23 0.043(3) 0.046(3) 0.040(3) 0.003(3) -0.003(3) 0.005(3) O5' 0.035(4) 0.027(3) 0.033(4) 0.004(3) -0.004(4) 0.000(4) O6' 0.039(3) 0.028(3) 0.033(3) 0.005(3) -0.005(3) 0.003(3) C8' 0.0243(15) 0.0269(15) 0.0334(18) 0.0021(16) -0.0008(16) -0.0001(13) C12' 0.0253(16) 0.0253(16) 0.0313(18) 0.0028(16) -0.0023(16) -0.0003(14) C20' 0.0296(15) 0.0254(15) 0.0319(16) 0.0041(15) -0.0034(16) 0.0010(14) C21' 0.035(3) 0.026(3) 0.033(3) 0.005(2) -0.004(3) 0.000(3) C22' 0.042(3) 0.034(3) 0.033(3) 0.005(3) -0.003(3) 0.003(3) C23' 0.043(4) 0.040(4) 0.036(4) 0.005(4) -0.001(4) 0.003(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C9 O3 C10 116.1(5) . . ? C6 C1 C2 121.2(5) . . ? C6 C1 H1A 119.4 . . ? C2 C1 H1A 119.4 . . ? C3 C2 C1 118.6(6) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? C2 C3 C4 121.6(6) . . ? C2 C3 Br1 119.7(5) . . ? C4 C3 Br1 118.6(5) . . ? C3 C4 C5 119.4(6) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C4 C5 C6 120.5(6) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C1 C6 C5 118.7(5) . . ? C1 C6 C7 122.8(5) . . ? C5 C6 C7 118.5(5) . . ? O1 C7 C6 120.9(5) . . ? O1 C7 C8' 119.4(5) . . ? C6 C7 C8' 119.6(5) . . ? O1 C7 C8 119.4(5) . . ? C6 C7 C8 119.6(5) . . ? O2 C9 O3 124.1(5) . . ? O2 C9 C8' 124.9(5) . . ? O3 C9 C8' 111.0(5) . . ? O2 C9 C8 124.9(5) . . ? O3 C9 C8 111.0(5) . . ? O3 C10 C11 111.1(5) . . ? O3 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? O3 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C14 C13 C18 120.5(5) . . ? C14 C13 H13A 119.8 . . ? C18 C13 H13A 119.8 . . ? C15 C14 C13 120.0(5) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 C15 C16 121.1(6) . . ? C14 C15 Br2 119.3(5) . . ? C16 C15 Br2 119.6(5) . . ? C17 C16 C15 118.5(6) . . ? C17 C16 H16A 120.7 . . ? C15 C16 H16A 120.7 . . ? C16 C17 C18 121.0(5) . . ? C16 C17 H17A 119.5 . . ? C18 C17 H17A 119.5 . . ? C13 C18 C17 119.0(5) . . ? C13 C18 C19 122.5(5) . . ? C17 C18 C19 118.6(5) . . ? O4 C19 C18 121.7(6) . . ? O4 C19 C20' 120.0(6) . . ? C18 C19 C20' 118.3(5) . . ? O4 C19 C20 120.0(6) . . ? C18 C19 C20 118.3(5) . . ? C21 O6 C22 115.7(7) . . ? C9 C8 C7 108.4(4) . . ? C9 C8 C12 111.5(4) . . ? C7 C8 C12 108.0(4) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C12 C8 H8A 109.6 . . ? C20 C12 C8 113.1(5) . . ? C20 C12 H12A 109.0 . . ? C8 C12 H12A 109.0 . . ? C20 C12 H12B 109.0 . . ? C8 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C21 C20 C12 112.6(5) . . ? C21 C20 C19 111.5(5) . . ? C12 C20 C19 108.8(5) . . ? C21 C20 H20A 107.9 . . ? C12 C20 H20A 107.9 . . ? C19 C20 H20A 107.9 . . ? O5 C21 O6 125.4(10) . . ? O5 C21 C20 124.4(8) . . ? O6 C21 C20 110.2(7) . . ? O6 C22 C23 111.3(8) . . ? O6 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? O6 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21' O6' C22' 116(2) . . ? C9 C8' C7 108.4(4) . . ? C9 C8' C12' 111.5(4) . . ? C7 C8' C12' 108.0(4) . . ? C9 C8' H8'A 109.6 . . ? C7 C8' H8'A 109.6 . . ? C12' C8' H8'A 109.6 . . ? C20' C12' C8' 113.1(5) . . ? C20' C12' H12C 109.0 . . ? C8' C12' H12C 109.0 . . ? C20' C12' H12D 109.0 . . ? C8' C12' H12D 109.0 . . ? H12C C12' H12D 107.8 . . ? C12' C20' C19 108.8(5) . . ? C12' C20' C21' 108.5(12) . . ? C19 C20' C21' 101.7(12) . . ? C12' C20' H20B 112.4 . . ? C19 C20' H20B 112.4 . . ? C21' C20' H20B 112.4 . . ? O5' C21' O6' 125(3) . . ? O5' C21' C20' 124(3) . . ? O6' C21' C20' 112(2) . . ? O6' C22' C23' 113(2) . . ? O6' C22' H22C 109.0 . . ? C23' C22' H22C 109.0 . . ? O6' C22' H22D 109.0 . . ? C23' C22' H22D 109.0 . . ? H22C C22' H22D 107.8 . . ? C22' C23' H23D 109.5 . . ? C22' C23' H23E 109.5 . . ? H23D C23' H23E 109.5 . . ? C22' C23' H23F 109.5 . . ? H23D C23' H23F 109.5 . . ? H23E C23' H23F 109.5 . . ? 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 C3 1.889(6) . ? Br2 C15 1.884(6) . ? O1 C7 1.230(8) . ? O2 C9 1.205(7) . ? O3 C9 1.332(7) . ? O3 C10 1.454(7) . ? O4 C19 1.208(7) . ? C1 C6 1.390(9) . ? C1 C2 1.395(8) . ? C1 H1A 0.9500 . ? C2 C3 1.377(9) . ? C2 H2A 0.9500 . ? C3 C4 1.381(10) . ? C4 C5 1.386(9) . ? C4 H4A 0.9500 . ? C5 C6 1.399(8) . ? C5 H5A 0.9500 . ? C6 C7 1.481(8) . ? C7 C8' 1.525(7) . ? C7 C8 1.525(7) . ? C9 C8' 1.524(7) . ? C9 C8 1.524(7) . ? C10 C11 1.488(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C13 C14 1.385(9) . ? C13 C18 1.395(8) . ? C13 H13A 0.9500 . ? C14 C15 1.382(9) . ? C14 H14A 0.9500 . ? C15 C16 1.401(8) . ? C16 C17 1.390(9) . ? C16 H16A 0.9500 . ? C17 C18 1.406(8) . ? C17 H17A 0.9500 . ? C18 C19 1.497(8) . ? C19 C20' 1.536(8) . ? C19 C20 1.536(8) . ? O5 C21 1.207(12) . ? O6 C21 1.333(11) . ? O6 C22 1.451(11) . ? C8 C12 1.547(7) . ? C8 H8A 1.0000 . ? C12 C20 1.533(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C20 C21 1.526(13) . ? C20 H20A 1.0000 . ? C22 C23 1.488(13) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O5' C21' 1.26(4) . ? O6' C21' 1.38(3) . ? O6' C22' 1.38(3) . ? C8' C12' 1.547(7) . ? C8' H8'A 1.0000 . ? C12' C20' 1.533(7) . ? C12' H12C 0.9900 . ? C12' H12D 0.9900 . ? C20' C21' 1.55(3) . ? C20' H20B 1.0000 . ? C22' C23' 1.45(4) . ? C22' H22C 0.9900 . ? C22' H22D 0.9900 . ? C23' H23D 0.9800 . ? C23' H23E 0.9800 . ? C23' H23F 0.9800 . ? 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 C6 C1 C2 C3 1.4(9) . . . . ? C1 C2 C3 C4 -1.6(10) . . . . ? C1 C2 C3 Br1 -179.1(5) . . . . ? C2 C3 C4 C5 1.6(10) . . . . ? Br1 C3 C4 C5 179.1(5) . . . . ? C3 C4 C5 C6 -1.3(9) . . . . ? C2 C1 C6 C5 -1.1(8) . . . . ? C2 C1 C6 C7 178.6(5) . . . . ? C4 C5 C6 C1 1.0(8) . . . . ? C4 C5 C6 C7 -178.6(5) . . . . ? C1 C6 C7 O1 177.9(5) . . . . ? C5 C6 C7 O1 -2.4(8) . . . . ? C1 C6 C7 C8' 0.6(8) . . . . ? C5 C6 C7 C8' -179.8(5) . . . . ? C1 C6 C7 C8 0.6(8) . . . . ? C5 C6 C7 C8 -179.8(5) . . . . ? C10 O3 C9 O2 -0.1(9) . . . . ? C10 O3 C9 C8' 179.9(5) . . . . ? C10 O3 C9 C8 179.9(5) . . . . ? C9 O3 C10 C11 -93.3(7) . . . . ? C18 C13 C14 C15 -0.5(9) . . . . ? C13 C14 C15 C16 0.7(10) . . . . ? C13 C14 C15 Br2 -176.3(5) . . . . ? C14 C15 C16 C17 -0.1(10) . . . . ? Br2 C15 C16 C17 176.9(5) . . . . ? C15 C16 C17 C18 -0.7(10) . . . . ? C14 C13 C18 C17 -0.4(9) . . . . ? C14 C13 C18 C19 179.1(6) . . . . ? C16 C17 C18 C13 1.0(9) . . . . ? C16 C17 C18 C19 -178.5(6) . . . . ? C13 C18 C19 O4 167.6(6) . . . . ? C17 C18 C19 O4 -12.8(9) . . . . ? C13 C18 C19 C20' -10.8(9) . . . . ? C17 C18 C19 C20' 168.7(5) . . . . ? C13 C18 C19 C20 -10.8(9) . . . . ? C17 C18 C19 C20 168.7(5) . . . . ? O2 C9 C8 C7 -114.9(6) . . . . ? O3 C9 C8 C7 65.1(6) . . . . ? O2 C9 C8 C12 3.8(9) . . . . ? O3 C9 C8 C12 -176.1(5) . . . . ? O1 C7 C8 C9 34.4(7) . . . . ? C6 C7 C8 C9 -148.2(5) . . . . ? O1 C7 C8 C12 -86.6(6) . . . . ? C6 C7 C8 C12 90.8(6) . . . . ? C9 C8 C12 C20 69.7(6) . . . . ? C7 C8 C12 C20 -171.3(5) . . . . ? C8 C12 C20 C21 65.1(6) . . . . ? C8 C12 C20 C19 -170.7(4) . . . . ? O4 C19 C20 C21 37.9(8) . . . . ? C18 C19 C20 C21 -143.5(6) . . . . ? O4 C19 C20 C12 -86.9(7) . . . . ? C18 C19 C20 C12 91.6(6) . . . . ? C22 O6 C21 O5 -6.7(12) . . . . ? C22 O6 C21 C20 172.3(6) . . . . ? C12 C20 C21 O5 16.8(10) . . . . ? C19 C20 C21 O5 -105.9(9) . . . . ? C12 C20 C21 O6 -162.3(6) . . . . ? C19 C20 C21 O6 75.1(7) . . . . ? C21 O6 C22 C23 83.5(9) . . . . ? O2 C9 C8' C7 -114.9(6) . . . . ? O3 C9 C8' C7 65.1(6) . . . . ? O2 C9 C8' C12' 3.8(9) . . . . ? O3 C9 C8' C12' -176.1(5) . . . . ? O1 C7 C8' C9 34.4(7) . . . . ? C6 C7 C8' C9 -148.2(5) . . . . ? O1 C7 C8' C12' -86.6(6) . . . . ? C6 C7 C8' C12' 90.8(6) . . . . ? C9 C8' C12' C20' 69.7(6) . . . . ? C7 C8' C12' C20' -171.3(5) . . . . ? C8' C12' C20' C19 -170.7(4) . . . . ? C8' C12' C20' C21' 79.5(12) . . . . ? O4 C19 C20' C12' -86.9(7) . . . . ? C18 C19 C20' C12' 91.6(6) . . . . ? O4 C19 C20' C21' 27.5(13) . . . . ? C18 C19 C20' C21' -154.0(12) . . . . ? C22' O6' C21' O5' -7(4) . . . . ? C22' O6' C21' C20' 174.6(19) . . . . ? C12' C20' C21' O5' -1(3) . . . . ? C19 C20' C21' O5' -116(2) . . . . ? C12' C20' C21' O6' 177.7(16) . . . . ? C19 C20' C21' O6' 63(2) . . . . ? C21' O6' C22' C23' -93(3) . . . . ?