#------------------------------------------------------------------------------ #$Date: 2016-08-07 11:21:30 +0300 (Sun, 07 Aug 2016) $ #$Revision: 185222 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225243.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_7225243 loop_ _publ_author_name 'Wojciechowski, Jonathan P.' 'Martin, Adam D.' 'Bhadbhade, Mohan' 'Webb, James E. A.' 'Thordarson, Pall' _publ_section_title ; Halogen bonding influences perylene-core twists in non-core substituted perylene tetraesters ; _journal_issue 24 _journal_name_full CrystEngComm _journal_page_first 4513 _journal_paper_doi 10.1039/C6CE00929H _journal_volume 18 _journal_year 2016 _chemical_formula_moiety '2(C H Br3), C32 H28 O8' _chemical_formula_sum 'C34 H30 Br6 O8' _chemical_formula_weight 1046.04 _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' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _audit_creation_date 2015-10-13 _audit_creation_method ; Olex2 1.2 (compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103) ; _audit_update_record ; 2016-03-14 deposited with the CCDC. 2016-05-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3120(15) _cell_length_b 23.629(5) _cell_length_c 20.889(4) _cell_measurement_temperature 100 _cell_volume 3609.1(13) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Australian Synchrotron' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0892 _diffrn_reflns_av_unetI/netI 0.0464 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 69506 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 30.085 _diffrn_reflns_theta_min 1.301 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 6.724 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.925 _exptl_crystal_description plate _exptl_crystal_F_000 2032 _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.015 _exptl_crystal_size_min 0.015 _refine_diff_density_max 1.196 _refine_diff_density_min -1.199 _refine_diff_density_rms 0.144 _refine_ls_abs_structure_details ; Flack x determined using 4873 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.487(9) _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 437 _refine_ls_number_reflns 10581 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0498 _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^)+(0.0826P)^2^+10.6738P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1304 _refine_ls_wR_factor_ref 0.1310 _reflns_Friedel_coverage 0.948 _reflns_Friedel_fraction_full 0.995 _reflns_Friedel_fraction_max 0.996 _reflns_number_gt 10341 _reflns_number_total 10581 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00929h2.cif _cod_data_source_block jono_4_a _cod_depositor_comments 'Adding full bibliography for 7225240--7225243.cif.' _cod_database_code 7225243 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C1A(H1A), C1B(H1B) 2.b Secondary CH2 refined with riding coordinates: C22(H22A,H22B), C25(H25A,H25B), C28(H28A,H28B), C31(H31A,H31B) 2.c Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12) 2.d Idealised Me refined as rotating group: C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C29(H29A,H29B,H29C), C32(H32A,H32B, H32C) ; _shelx_res_file ; jono_4_a.res created by SHELXL-2014/7 TITL Jono_4_a.res in Pna2(1) REM Old TITL Jono_4 in Pna2(1) REM SHELXT solution in Pna2(1) REM R1 0.118, Rweak 0.018, Alpha 0.007, Orientation as input REM Flack x = 0.224 ( 0.051 ) from Parsons' quotients REM Formula found by SHELXT: C33 N4 O5 Cl6 CELL 0.71073 7.312 23.629 20.889 90 90 90 ZERR 4 0.0015 0.0047 0.0042 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,0.5+Z SFAC C H Br O UNIT 136 120 24 32 L.S. 10 PLAN 20 TEMP -173.15 BOND $H LIST 6 MORE -1 CONF fmap 2 acta 52 REM REM REM WGHT 0.082600 10.673800 FVAR 0.22799 BR1A 3 0.040061 0.328673 0.197899 11.00000 0.02158 0.01508 = 0.02480 -0.00029 0.00320 -0.00080 BR2A 3 0.467539 0.333268 0.187998 11.00000 0.02127 0.01604 = 0.02541 0.00061 -0.00080 -0.00133 BR3A 3 0.237058 0.290215 0.068416 11.00000 0.03446 0.03586 = 0.01733 -0.00145 -0.00074 0.00123 C1A 1 0.250441 0.294109 0.159663 11.00000 0.01936 0.01771 = 0.01647 0.00483 0.00127 0.00031 AFIX 13 H1A 2 0.257813 0.254424 0.176092 11.00000 -1.20000 AFIX 0 BR1B 3 0.365913 0.162404 0.825283 11.00000 0.01935 0.01833 = 0.03290 -0.00015 0.00181 0.00131 BR2B 3 -0.057184 0.169624 0.799560 11.00000 0.02036 0.01799 = 0.02114 -0.00165 -0.00327 0.00125 BR3B 3 0.100925 0.214229 0.931823 11.00000 0.03031 0.03144 = 0.01677 -0.00214 0.00016 -0.00315 C1B 1 0.147374 0.205402 0.842171 11.00000 0.01754 0.01547 = 0.01856 -0.00092 -0.00218 -0.00097 AFIX 13 H1B 2 0.163752 0.243945 0.823249 11.00000 -1.20000 AFIX 0 O1 4 0.262339 0.110485 0.258008 11.00000 0.02546 0.02057 = 0.01509 -0.00322 0.00299 0.00079 O2 4 0.091553 0.075232 0.337775 11.00000 0.01977 0.01601 = 0.01659 -0.00382 0.00181 -0.00302 O3 4 0.466935 0.054816 0.375804 11.00000 0.01843 0.01589 = 0.02464 -0.00047 0.00568 0.00366 O4 4 0.305261 0.003295 0.446099 11.00000 0.02633 0.01050 = 0.02212 -0.00061 0.00461 0.00079 O5 4 0.157242 0.397577 0.747360 11.00000 0.02529 0.01857 = 0.01361 -0.00217 -0.00083 -0.00172 O6 4 0.012598 0.434882 0.662241 11.00000 0.01830 0.01605 = 0.01674 -0.00605 -0.00136 0.00125 O7 4 0.395073 0.457502 0.642268 11.00000 0.02037 0.01862 = 0.02326 0.00075 -0.00535 -0.00559 O8 4 0.261348 0.506069 0.562470 11.00000 0.02791 0.01216 = 0.02246 -0.00281 -0.00587 -0.00174 C1 1 0.243089 0.263180 0.368409 11.00000 0.02582 0.01561 = 0.01327 0.00101 0.00365 0.00192 AFIX 43 H1 2 0.246008 0.299401 0.348698 11.00000 -1.20000 AFIX 0 C2 1 0.237241 0.214721 0.330536 11.00000 0.02594 0.01458 = 0.01585 0.00065 -0.00027 0.00129 AFIX 43 H2 2 0.229529 0.218420 0.285331 11.00000 -1.20000 AFIX 0 C3 1 0.242471 0.161161 0.357605 11.00000 0.01506 0.01237 = 0.01429 -0.00129 0.00260 -0.00048 C4 1 0.291124 0.102013 0.456056 11.00000 0.01226 0.01173 = 0.01566 0.00212 -0.00071 0.00165 C5 1 0.278257 0.098757 0.521913 11.00000 0.01684 0.01160 = 0.01920 0.00254 -0.00156 0.00080 AFIX 43 H5 2 0.296371 0.063254 0.542292 11.00000 -1.20000 AFIX 0 C6 1 0.239466 0.146072 0.559287 11.00000 0.02016 0.01400 = 0.01347 -0.00191 -0.00251 -0.00363 AFIX 43 H6 2 0.221854 0.141877 0.604095 11.00000 -1.20000 AFIX 0 C7 1 0.150218 0.246449 0.634561 11.00000 0.01914 0.01311 = 0.01459 0.00040 -0.00031 -0.00012 AFIX 43 H7 2 0.130801 0.210322 0.653323 11.00000 -1.20000 AFIX 0 C8 1 0.130822 0.295309 0.671971 11.00000 0.01988 0.01868 = 0.01069 0.00251 0.00017 0.00105 AFIX 43 H8 2 0.095437 0.291686 0.715538 11.00000 -1.20000 AFIX 0 C9 1 0.161665 0.348249 0.647246 11.00000 0.01407 0.01560 = 0.01518 -0.00270 0.00057 0.00072 C10 1 0.266202 0.407563 0.553473 11.00000 0.01068 0.01323 = 0.01737 -0.00022 0.00078 0.00054 C11 1 0.296223 0.410801 0.488389 11.00000 0.01777 0.01124 = 0.01928 0.00238 0.00033 0.00084 AFIX 43 H11 2 0.324681 0.446425 0.469808 11.00000 -1.20000 AFIX 0 C12 1 0.285883 0.363045 0.449034 11.00000 0.01706 0.01476 = 0.01354 0.00012 0.00280 0.00236 AFIX 43 H12 2 0.302312 0.366925 0.404135 11.00000 -1.20000 AFIX 0 C13 1 0.226336 0.199325 0.531565 11.00000 0.00975 0.01133 = 0.01544 -0.00101 -0.00166 -0.00179 C14 1 0.197590 0.250328 0.570267 11.00000 0.01061 0.00928 = 0.01629 -0.00051 0.00015 -0.00075 C15 1 0.222471 0.305057 0.542923 11.00000 0.01095 0.01204 = 0.01312 -0.00084 -0.00018 -0.00132 C16 1 0.251781 0.309960 0.475040 11.00000 0.01241 0.00981 = 0.01465 -0.00044 0.00067 0.00157 C17 1 0.244695 0.259060 0.434728 11.00000 0.01309 0.01171 = 0.01647 0.00177 -0.00016 0.00151 C18 1 0.243967 0.204531 0.463754 11.00000 0.01019 0.00971 = 0.01227 -0.00051 -0.00030 -0.00084 C19 1 0.218515 0.354648 0.581744 11.00000 0.00752 0.01386 = 0.01554 -0.00065 -0.00099 0.00032 C20 1 0.260561 0.155046 0.424664 11.00000 0.01063 0.01215 = 0.01208 -0.00079 -0.00168 -0.00015 C21 1 0.206752 0.112837 0.312743 11.00000 0.01788 0.01380 = 0.01476 -0.00028 -0.00067 0.00471 C22 1 0.050592 0.025843 0.298468 11.00000 0.02376 0.01485 = 0.02453 -0.00665 -0.00109 -0.00250 AFIX 23 H22A 2 0.162440 0.003030 0.291586 11.00000 -1.20000 H22B 2 0.002434 0.037711 0.256257 11.00000 -1.20000 AFIX 0 C23 1 -0.090173 -0.008046 0.334016 11.00000 0.02237 0.01959 = 0.03585 -0.00327 0.00093 -0.00218 AFIX 137 H23A 2 -0.110942 -0.043968 0.311723 11.00000 -1.50000 H23B 2 -0.204926 0.013310 0.335992 11.00000 -1.50000 H23C 2 -0.046576 -0.015610 0.377546 11.00000 -1.50000 AFIX 0 C24 1 0.363827 0.052253 0.420863 11.00000 0.01553 0.01431 = 0.01861 0.00069 -0.00083 0.00346 C25 1 0.385527 -0.047842 0.418616 11.00000 0.04164 0.01295 = 0.02512 0.00065 -0.00021 0.00984 AFIX 23 H25A 2 0.519021 -0.048939 0.426430 11.00000 -1.20000 H25B 2 0.363502 -0.049406 0.371888 11.00000 -1.20000 AFIX 0 C26 1 0.291798 -0.096305 0.451893 11.00000 0.04896 0.01424 = 0.03401 -0.00125 0.00099 -0.00414 AFIX 137 H26A 2 0.340308 -0.132190 0.435617 11.00000 -1.50000 H26B 2 0.159982 -0.094474 0.443666 11.00000 -1.50000 H26C 2 0.314061 -0.093814 0.498070 11.00000 -1.50000 AFIX 0 C27 1 0.116488 0.396481 0.690921 11.00000 0.01500 0.01476 = 0.01494 -0.00104 0.00155 -0.00238 C28 1 -0.036767 0.484494 0.700845 11.00000 0.02181 0.02147 = 0.02481 -0.00945 0.00130 0.00320 AFIX 23 H28A 2 0.072873 0.507752 0.709849 11.00000 -1.20000 H28B 2 -0.091240 0.472523 0.742066 11.00000 -1.20000 AFIX 0 C29 1 -0.172273 0.517551 0.662520 11.00000 0.02054 0.01844 = 0.03884 -0.00432 -0.00228 0.00354 AFIX 137 H29A 2 -0.116039 0.529473 0.622126 11.00000 -1.50000 H29B 2 -0.210458 0.551012 0.686805 11.00000 -1.50000 H29C 2 -0.279194 0.493851 0.653494 11.00000 -1.50000 AFIX 0 C30 1 0.311888 0.458544 0.592111 11.00000 0.01359 0.01310 = 0.01992 -0.00308 -0.00042 -0.00098 C31 1 0.322879 0.558834 0.591380 11.00000 0.03882 0.01270 = 0.02376 -0.00159 -0.00516 -0.00699 AFIX 23 H31A 2 0.458151 0.560284 0.592551 11.00000 -1.20000 H31B 2 0.276134 0.562132 0.635702 11.00000 -1.20000 AFIX 0 C32 1 0.248879 0.605851 0.550558 11.00000 0.05472 0.01423 = 0.03492 0.00160 -0.01054 0.00070 AFIX 137 H32A 2 0.297328 0.602282 0.507003 11.00000 -1.50000 H32B 2 0.285916 0.642372 0.568621 11.00000 -1.50000 H32C 2 0.115093 0.603589 0.549406 11.00000 -1.50000 AFIX 0 HKLF 4 REM Jono_4_a.res in Pna2(1) REM R1 = 0.0498 for 10341 Fo > 4sig(Fo) and 0.0506 for all 10581 data REM 437 parameters refined using 1 restraints END WGHT 0.0826 10.6606 REM Highest difference peak 1.196, deepest hole -1.199, 1-sigma level 0.144 Q1 1 0.3794 0.1683 0.8626 11.00000 0.05 1.20 Q2 1 0.1588 0.1890 0.9368 11.00000 0.05 1.07 Q3 1 0.4593 0.3381 0.1521 11.00000 0.05 1.06 Q4 1 0.0312 0.3264 0.1615 11.00000 0.05 1.04 Q5 1 0.1132 0.2142 0.8967 11.00000 0.05 1.01 Q6 1 0.2356 0.2888 0.1049 11.00000 0.05 1.00 Q7 1 -0.0487 0.1680 0.7621 11.00000 0.05 0.93 Q8 1 -0.0411 0.1523 0.8312 11.00000 0.05 0.91 Q9 1 -0.0403 0.1793 0.8328 11.00000 0.05 0.84 Q10 1 0.2666 0.3175 0.0623 11.00000 0.05 0.84 Q11 1 0.4476 0.3200 0.2231 11.00000 0.05 0.84 Q12 1 0.0401 0.3233 0.2375 11.00000 0.05 0.83 Q13 1 0.2353 0.2811 0.0373 11.00000 0.05 0.82 Q14 1 0.1099 0.2308 0.9627 11.00000 0.05 0.80 Q15 1 0.2472 0.3074 0.0412 11.00000 0.05 0.77 Q16 1 0.1627 0.2373 0.9478 11.00000 0.05 0.77 Q17 1 0.2867 0.1824 0.8317 11.00000 0.05 0.76 Q18 1 0.3187 0.1393 0.8011 11.00000 0.05 0.75 Q19 1 0.4428 0.1831 0.8179 11.00000 0.05 0.71 Q20 1 0.1951 0.2221 0.5498 11.00000 0.05 0.66 ; _shelx_res_checksum 82280 _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn Br1A Br 0.04006(9) 0.32867(3) 0.19790(3) 0.02049(15) Uani 1 1 d . Br2A Br 0.46754(10) 0.33327(3) 0.18800(4) 0.02091(15) Uani 1 1 d . Br3A Br 0.23706(12) 0.29022(4) 0.06842(4) 0.02922(17) Uani 1 1 d . C1A C 0.2504(9) 0.2941(3) 0.1597(3) 0.0178(12) Uani 1 1 d . H1A H 0.2578 0.2544 0.1761 0.021 Uiso 1 1 calc R Br1B Br 0.36591(10) 0.16240(3) 0.82528(4) 0.02353(15) Uani 1 1 d . Br2B Br -0.05718(9) 0.16962(3) 0.79956(3) 0.01983(14) Uani 1 1 d . Br3B Br 0.10092(11) 0.21423(3) 0.93182(4) 0.02617(16) Uani 1 1 d . C1B C 0.1474(9) 0.2054(3) 0.8422(3) 0.0172(11) Uani 1 1 d . H1B H 0.1638 0.2439 0.8232 0.021 Uiso 1 1 calc R O1 O 0.2623(7) 0.1105(2) 0.2580(2) 0.0204(9) Uani 1 1 d . O2 O 0.0916(7) 0.0752(2) 0.3378(2) 0.0175(8) Uani 1 1 d . O3 O 0.4669(7) 0.0548(2) 0.3758(2) 0.0197(9) Uani 1 1 d . O4 O 0.3053(8) 0.00330(19) 0.4461(2) 0.0196(9) Uani 1 1 d . O5 O 0.1572(7) 0.3976(2) 0.7474(2) 0.0192(9) Uani 1 1 d . O6 O 0.0126(7) 0.4349(2) 0.6622(2) 0.0170(8) Uani 1 1 d . O7 O 0.3951(7) 0.4575(2) 0.6423(2) 0.0208(9) Uani 1 1 d . O8 O 0.2613(7) 0.5061(2) 0.5625(3) 0.0208(9) Uani 1 1 d . C1 C 0.2431(9) 0.2632(3) 0.3684(3) 0.0182(12) Uani 1 1 d . H1 H 0.2460 0.2994 0.3487 0.022 Uiso 1 1 calc R C2 C 0.2372(10) 0.2147(3) 0.3305(3) 0.0188(12) Uani 1 1 d . H2 H 0.2295 0.2184 0.2853 0.023 Uiso 1 1 calc R C3 C 0.2425(8) 0.1612(3) 0.3576(3) 0.0139(10) Uani 1 1 d . C4 C 0.2911(8) 0.1020(2) 0.4561(3) 0.0132(10) Uani 1 1 d . C5 C 0.2783(9) 0.0988(3) 0.5219(3) 0.0159(11) Uani 1 1 d . H5 H 0.2964 0.0633 0.5423 0.019 Uiso 1 1 calc R C6 C 0.2395(9) 0.1461(3) 0.5593(3) 0.0159(11) Uani 1 1 d . H6 H 0.2219 0.1419 0.6041 0.019 Uiso 1 1 calc R C7 C 0.1502(9) 0.2464(3) 0.6346(3) 0.0156(10) Uani 1 1 d . H7 H 0.1308 0.2103 0.6533 0.019 Uiso 1 1 calc R C8 C 0.1308(9) 0.2953(3) 0.6720(3) 0.0164(11) Uani 1 1 d . H8 H 0.0954 0.2917 0.7155 0.020 Uiso 1 1 calc R C9 C 0.1617(9) 0.3482(3) 0.6472(3) 0.0150(10) Uani 1 1 d . C10 C 0.2662(8) 0.4076(3) 0.5535(3) 0.0138(10) Uani 1 1 d . C11 C 0.2962(9) 0.4108(3) 0.4884(3) 0.0161(10) Uani 1 1 d . H11 H 0.3247 0.4464 0.4698 0.019 Uiso 1 1 calc R C12 C 0.2859(9) 0.3630(3) 0.4490(3) 0.0151(10) Uani 1 1 d . H12 H 0.3023 0.3669 0.4041 0.018 Uiso 1 1 calc R C13 C 0.2263(8) 0.1993(2) 0.5316(3) 0.0122(9) Uani 1 1 d . C14 C 0.1976(7) 0.2503(2) 0.5703(3) 0.0121(9) Uani 1 1 d . C15 C 0.2225(8) 0.3051(2) 0.5429(3) 0.0120(9) Uani 1 1 d . C16 C 0.2518(8) 0.3100(3) 0.4750(3) 0.0123(10) Uani 1 1 d . C17 C 0.2447(7) 0.2591(3) 0.4347(3) 0.0138(10) Uani 1 1 d . C18 C 0.2440(7) 0.2045(2) 0.4638(3) 0.0107(10) Uani 1 1 d . C19 C 0.2185(7) 0.3546(2) 0.5817(3) 0.0123(10) Uani 1 1 d . C20 C 0.2606(7) 0.1550(3) 0.4247(3) 0.0116(9) Uani 1 1 d . C21 C 0.2068(9) 0.1128(3) 0.3127(3) 0.0155(10) Uani 1 1 d . C22 C 0.0506(10) 0.0258(3) 0.2985(4) 0.0210(12) Uani 1 1 d . H22A H 0.1624 0.0030 0.2916 0.025 Uiso 1 1 calc R H22B H 0.0024 0.0377 0.2563 0.025 Uiso 1 1 calc R C23 C -0.0902(10) -0.0080(3) 0.3340(4) 0.0259(14) Uani 1 1 d . H23A H -0.1109 -0.0440 0.3117 0.039 Uiso 1 1 calc GR H23B H -0.2049 0.0133 0.3360 0.039 Uiso 1 1 calc GR H23C H -0.0466 -0.0156 0.3775 0.039 Uiso 1 1 calc GR C24 C 0.3638(8) 0.0523(3) 0.4209(3) 0.0162(11) Uani 1 1 d . C25 C 0.3855(12) -0.0478(3) 0.4186(4) 0.0266(15) Uani 1 1 d . H25A H 0.5190 -0.0489 0.4264 0.032 Uiso 1 1 calc R H25B H 0.3635 -0.0494 0.3719 0.032 Uiso 1 1 calc R C26 C 0.2918(15) -0.0963(3) 0.4519(4) 0.0324(17) Uani 1 1 d . H26A H 0.3403 -0.1322 0.4356 0.049 Uiso 1 1 calc GR H26B H 0.1600 -0.0945 0.4437 0.049 Uiso 1 1 calc GR H26C H 0.3141 -0.0938 0.4981 0.049 Uiso 1 1 calc GR C27 C 0.1165(8) 0.3965(3) 0.6909(3) 0.0149(10) Uani 1 1 d . C28 C -0.0368(10) 0.4845(3) 0.7008(4) 0.0227(13) Uani 1 1 d . H28A H 0.0729 0.5078 0.7098 0.027 Uiso 1 1 calc R H28B H -0.0912 0.4725 0.7421 0.027 Uiso 1 1 calc R C29 C -0.1723(10) 0.5176(3) 0.6625(4) 0.0259(14) Uani 1 1 d . H29A H -0.1160 0.5295 0.6221 0.039 Uiso 1 1 calc GR H29B H -0.2105 0.5510 0.6868 0.039 Uiso 1 1 calc GR H29C H -0.2792 0.4939 0.6535 0.039 Uiso 1 1 calc GR C30 C 0.3119(8) 0.4585(3) 0.5921(3) 0.0155(10) Uani 1 1 d . C31 C 0.3229(12) 0.5588(3) 0.5914(4) 0.0251(14) Uani 1 1 d . H31A H 0.4582 0.5603 0.5926 0.030 Uiso 1 1 calc R H31B H 0.2761 0.5621 0.6357 0.030 Uiso 1 1 calc R C32 C 0.2489(14) 0.6059(3) 0.5506(5) 0.0346(19) Uani 1 1 d . H32A H 0.2973 0.6023 0.5070 0.052 Uiso 1 1 calc GR H32B H 0.2859 0.6424 0.5686 0.052 Uiso 1 1 calc GR H32C H 0.1151 0.6036 0.5494 0.052 Uiso 1 1 calc GR loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1A 0.0216(3) 0.0151(3) 0.0248(3) -0.0003(2) 0.0032(2) -0.0008(2) Br2A 0.0213(3) 0.0160(3) 0.0254(3) 0.0006(2) -0.0008(3) -0.0013(2) Br3A 0.0345(4) 0.0359(4) 0.0173(3) -0.0015(3) -0.0007(3) 0.0012(3) C1A 0.019(3) 0.018(3) 0.016(3) 0.005(2) 0.001(2) 0.000(2) Br1B 0.0194(3) 0.0183(3) 0.0329(4) -0.0001(2) 0.0018(3) 0.0013(2) Br2B 0.0204(3) 0.0180(3) 0.0211(3) -0.0017(2) -0.0033(2) 0.0012(2) Br3B 0.0303(3) 0.0314(4) 0.0168(3) -0.0021(3) 0.0002(3) -0.0031(3) C1B 0.018(3) 0.015(3) 0.019(3) -0.001(2) -0.002(2) -0.001(2) O1 0.025(2) 0.021(2) 0.015(2) -0.0032(17) 0.0030(17) 0.0008(18) O2 0.020(2) 0.016(2) 0.0166(19) -0.0038(15) 0.0018(17) -0.0030(17) O3 0.018(2) 0.016(2) 0.025(2) -0.0005(17) 0.0057(17) 0.0037(17) O4 0.026(2) 0.0105(19) 0.022(2) -0.0006(16) 0.0046(18) 0.0008(18) O5 0.025(2) 0.019(2) 0.0136(19) -0.0022(15) -0.0008(17) -0.0017(18) O6 0.018(2) 0.016(2) 0.0167(19) -0.0061(16) -0.0014(16) 0.0012(17) O7 0.020(2) 0.019(2) 0.023(2) 0.0008(17) -0.0054(18) -0.0056(18) O8 0.028(2) 0.012(2) 0.022(2) -0.0028(17) -0.0059(19) -0.0017(17) C1 0.026(3) 0.016(3) 0.013(3) 0.001(2) 0.004(2) 0.002(2) C2 0.026(3) 0.015(3) 0.016(3) 0.001(2) 0.000(2) 0.001(2) C3 0.015(3) 0.012(2) 0.014(2) -0.001(2) 0.0026(19) -0.0005(18) C4 0.012(2) 0.012(2) 0.016(2) 0.0021(19) -0.0007(19) 0.002(2) C5 0.017(3) 0.012(2) 0.019(3) 0.003(2) -0.002(2) 0.001(2) C6 0.020(3) 0.014(3) 0.013(3) -0.002(2) -0.003(2) -0.004(2) C7 0.019(3) 0.013(2) 0.015(2) 0.0004(19) 0.000(2) 0.000(2) C8 0.020(3) 0.019(3) 0.011(2) 0.003(2) 0.000(2) 0.001(2) C9 0.014(2) 0.016(2) 0.015(2) -0.003(2) 0.001(2) 0.001(2) C10 0.011(2) 0.013(2) 0.017(3) 0.000(2) 0.0008(19) 0.0005(19) C11 0.018(3) 0.011(2) 0.019(3) 0.002(2) 0.000(2) 0.001(2) C12 0.017(3) 0.015(3) 0.014(2) 0.0001(19) 0.003(2) 0.002(2) C13 0.010(2) 0.011(2) 0.015(2) -0.001(2) -0.0017(18) -0.0018(18) C14 0.011(2) 0.009(2) 0.016(2) -0.0005(19) 0.0002(19) -0.0007(19) C15 0.011(2) 0.012(2) 0.013(2) -0.0008(19) -0.0002(18) -0.0013(19) C16 0.012(2) 0.010(2) 0.015(2) -0.0004(19) 0.0007(17) 0.0016(18) C17 0.013(2) 0.012(2) 0.016(3) 0.002(2) 0.000(2) 0.0015(18) C18 0.010(2) 0.010(2) 0.012(2) -0.0005(18) -0.0003(17) -0.0008(17) C19 0.008(2) 0.014(2) 0.016(2) -0.0007(19) -0.0010(18) 0.0003(18) C20 0.011(2) 0.012(2) 0.012(2) -0.0008(19) -0.0017(18) -0.0001(17) C21 0.018(2) 0.014(2) 0.015(3) -0.0003(19) -0.001(2) 0.005(2) C22 0.024(3) 0.015(3) 0.025(3) -0.007(2) -0.001(3) -0.003(2) C23 0.022(3) 0.020(3) 0.036(4) -0.003(3) 0.001(3) -0.002(2) C24 0.016(2) 0.014(3) 0.019(3) 0.001(2) -0.001(2) 0.003(2) C25 0.042(4) 0.013(3) 0.025(3) 0.001(2) 0.000(3) 0.010(3) C26 0.049(5) 0.014(3) 0.034(4) -0.001(3) 0.001(4) -0.004(3) C27 0.015(2) 0.015(2) 0.015(2) -0.001(2) 0.002(2) -0.0024(19) C28 0.022(3) 0.021(3) 0.025(3) -0.009(3) 0.001(2) 0.003(2) C29 0.021(3) 0.018(3) 0.039(4) -0.004(3) -0.002(3) 0.004(2) C30 0.014(2) 0.013(2) 0.020(3) -0.003(2) 0.000(2) -0.001(2) C31 0.039(4) 0.013(3) 0.024(3) -0.002(2) -0.005(3) -0.007(3) C32 0.055(5) 0.014(3) 0.035(4) 0.002(3) -0.011(4) 0.001(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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle Br1A C1A Br2A 109.2(3) Br1A C1A H1A 107.5 Br2A C1A H1A 107.5 Br3A C1A Br1A 113.3(3) Br3A C1A Br2A 111.8(3) Br3A C1A H1A 107.5 Br1B C1B Br2B 109.1(3) Br1B C1B H1B 108.0 Br2B C1B H1B 108.0 Br3B C1B Br1B 112.6(3) Br3B C1B Br2B 111.1(3) Br3B C1B H1B 108.0 C21 O2 C22 116.3(5) C24 O4 C25 115.5(5) C27 O6 C28 116.0(5) C30 O8 C31 116.3(5) C2 C1 H1 119.7 C17 C1 H1 119.7 C17 C1 C2 120.6(6) C1 C2 H2 119.4 C3 C2 C1 121.2(6) C3 C2 H2 119.4 C2 C3 C20 120.0(6) C2 C3 C21 115.8(6) C20 C3 C21 123.9(5) C5 C4 C20 119.6(6) C5 C4 C24 118.3(5) C20 C4 C24 121.5(5) C4 C5 H5 119.1 C4 C5 C6 121.8(6) C6 C5 H5 119.1 C5 C6 H6 119.7 C13 C6 C5 120.5(6) C13 C6 H6 119.7 C8 C7 H7 119.7 C14 C7 H7 119.7 C14 C7 C8 120.6(6) C7 C8 H8 119.2 C9 C8 C7 121.6(6) C9 C8 H8 119.2 C8 C9 C19 120.1(6) C8 C9 C27 115.4(5) C19 C9 C27 124.3(5) C11 C10 C19 119.7(6) C11 C10 C30 117.0(5) C19 C10 C30 122.7(6) C10 C11 H11 119.1 C10 C11 C12 121.7(6) C12 C11 H11 119.1 C11 C12 H12 119.7 C16 C12 C11 120.6(6) C16 C12 H12 119.7 C6 C13 C14 121.7(6) C6 C13 C18 119.1(6) C18 C13 C14 119.3(5) C7 C14 C13 120.9(5) C7 C14 C15 118.6(5) C15 C14 C13 120.4(5) C14 C15 C16 119.1(5) C19 C15 C14 121.0(5) C19 C15 C16 119.8(5) C12 C16 C15 119.0(5) C12 C16 C17 121.4(5) C15 C16 C17 119.6(5) C1 C17 C16 121.0(6) C1 C17 C18 119.2(6) C18 C17 C16 119.8(5) C13 C18 C20 120.2(5) C17 C18 C13 120.1(5) C17 C18 C20 119.7(5) C10 C19 C9 123.8(5) C15 C19 C9 117.4(5) C15 C19 C10 118.7(5) C3 C20 C4 123.9(5) C3 C20 C18 118.3(5) C18 C20 C4 117.8(5) O1 C21 O2 123.4(6) O1 C21 C3 124.4(6) O2 C21 C3 111.9(5) O2 C22 H22A 110.4 O2 C22 H22B 110.4 O2 C22 C23 106.8(6) H22A C22 H22B 108.6 C23 C22 H22A 110.4 C23 C22 H22B 110.4 C22 C23 H23A 109.5 C22 C23 H23B 109.5 C22 C23 H23C 109.5 H23A C23 H23B 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 O3 C24 O4 123.3(6) O3 C24 C4 124.7(6) O4 C24 C4 112.0(5) O4 C25 H25A 110.7 O4 C25 H25B 110.7 O4 C25 C26 105.4(6) H25A C25 H25B 108.8 C26 C25 H25A 110.7 C26 C25 H25B 110.7 C25 C26 H26A 109.5 C25 C26 H26B 109.5 C25 C26 H26C 109.5 H26A C26 H26B 109.5 H26A C26 H26C 109.5 H26B C26 H26C 109.5 O5 C27 O6 124.3(6) O5 C27 C9 123.6(6) O6 C27 C9 111.8(5) O6 C28 H28A 110.4 O6 C28 H28B 110.4 O6 C28 C29 106.6(6) H28A C28 H28B 108.6 C29 C28 H28A 110.4 C29 C28 H28B 110.4 C28 C29 H29A 109.5 C28 C29 H29B 109.5 C28 C29 H29C 109.5 H29A C29 H29B 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 O7 C30 O8 123.9(6) O7 C30 C10 124.4(6) O8 C30 C10 111.6(5) O8 C31 H31A 110.4 O8 C31 H31B 110.4 O8 C31 C32 106.7(6) H31A C31 H31B 108.6 C32 C31 H31A 110.4 C32 C31 H31B 110.4 C31 C32 H32A 109.5 C31 C32 H32B 109.5 C31 C32 H32C 109.5 H32A C32 H32B 109.5 H32A C32 H32C 109.5 H32B C32 H32C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1A C1A 1.916(7) Br2A C1A 1.930(7) Br3A C1A 1.911(7) C1A H1A 1.0000 Br1B C1B 1.926(7) Br2B C1B 1.935(6) Br3B C1B 1.915(6) C1B H1B 1.0000 O1 C21 1.215(8) O2 C21 1.331(8) O2 C22 1.458(8) O3 C24 1.207(8) O4 C24 1.341(8) O4 C25 1.461(8) O5 C27 1.216(8) O6 C27 1.326(8) O6 C28 1.468(8) O7 C30 1.212(8) O8 C30 1.335(8) O8 C31 1.457(8) C1 H1 0.9500 C1 C2 1.392(9) C1 C17 1.389(8) C2 H2 0.9500 C2 C3 1.387(9) C3 C20 1.414(9) C3 C21 1.500(9) C4 C5 1.381(8) C4 C20 1.432(8) C4 C24 1.485(8) C5 H5 0.9500 C5 C6 1.393(9) C6 H6 0.9500 C6 C13 1.388(8) C7 H7 0.9500 C7 C8 1.401(9) C7 C14 1.390(8) C8 H8 0.9500 C8 C9 1.372(9) C9 C19 1.438(8) C9 C27 1.497(8) C10 C11 1.379(9) C10 C19 1.426(8) C10 C30 1.488(8) C11 H11 0.9500 C11 C12 1.398(8) C12 H12 0.9500 C12 C16 1.389(8) C13 C14 1.466(8) C13 C18 1.428(8) C14 C15 1.425(8) C15 C16 1.439(8) C15 C19 1.425(8) C16 C17 1.469(8) C17 C18 1.424(8) C18 C20 1.431(8) C22 H22A 0.9900 C22 H22B 0.9900 C22 C23 1.501(10) C23 H23A 0.9800 C23 H23B 0.9800 C23 H23C 0.9800 C25 H25A 0.9900 C25 H25B 0.9900 C25 C26 1.505(11) C26 H26A 0.9800 C26 H26B 0.9800 C26 H26C 0.9800 C28 H28A 0.9900 C28 H28B 0.9900 C28 C29 1.494(10) C29 H29A 0.9800 C29 H29B 0.9800 C29 H29C 0.9800 C31 H31A 0.9900 C31 H31B 0.9900 C31 C32 1.501(11) C32 H32A 0.9800 C32 H32B 0.9800 C32 H32C 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 C1 C2 C3 C20 -2.3(10) C1 C2 C3 C21 171.1(6) C1 C17 C18 C13 -173.5(6) C1 C17 C18 C20 6.4(8) C2 C1 C17 C16 179.7(6) C2 C1 C17 C18 1.2(9) C2 C3 C20 C4 -171.5(6) C2 C3 C20 C18 9.7(9) C2 C3 C21 O1 38.9(9) C2 C3 C21 O2 -134.9(6) C4 C5 C6 C13 -5.0(10) C5 C4 C20 C3 -169.8(6) C5 C4 C20 C18 9.0(8) C5 C4 C24 O3 -139.7(7) C5 C4 C24 O4 38.6(8) C5 C6 C13 C14 -175.9(6) C5 C6 C13 C18 3.1(9) C6 C13 C14 C7 -11.5(9) C6 C13 C14 C15 166.8(6) C6 C13 C18 C17 -175.3(5) C6 C13 C18 C20 4.8(8) C7 C8 C9 C19 -1.1(10) C7 C8 C9 C27 173.8(6) C7 C14 C15 C16 -173.3(5) C7 C14 C15 C19 6.7(8) C8 C7 C14 C13 177.2(6) C8 C7 C14 C15 -1.2(9) C8 C9 C19 C10 -175.3(6) C8 C9 C19 C15 6.3(9) C8 C9 C27 O5 43.9(9) C8 C9 C27 O6 -130.1(6) C10 C11 C12 C16 -2.6(10) C11 C10 C19 C9 -171.6(6) C11 C10 C19 C15 6.7(8) C11 C10 C30 O7 -134.7(7) C11 C10 C30 O8 40.9(8) C11 C12 C16 C15 1.6(9) C11 C12 C16 C17 -178.5(6) C12 C16 C17 C1 -10.2(9) C12 C16 C17 C18 168.2(6) C13 C14 C15 C16 8.3(8) C13 C14 C15 C19 -171.7(5) C13 C18 C20 C3 168.1(5) C13 C18 C20 C4 -10.8(8) C14 C7 C8 C9 -1.5(10) C14 C13 C18 C17 3.8(8) C14 C13 C18 C20 -176.1(5) C14 C15 C16 C12 -176.5(6) C14 C15 C16 C17 3.6(8) C14 C15 C19 C9 -9.1(8) C14 C15 C19 C10 172.4(5) C15 C16 C17 C1 169.6(6) C15 C16 C17 C18 -11.9(8) C16 C15 C19 C9 170.8(5) C16 C15 C19 C10 -7.6(8) C16 C17 C18 C13 8.1(8) C16 C17 C18 C20 -172.1(5) C17 C1 C2 C3 -3.4(10) C17 C18 C20 C3 -11.8(8) C17 C18 C20 C4 169.4(5) C18 C13 C14 C7 169.4(5) C18 C13 C14 C15 -12.2(8) C19 C9 C27 O5 -141.4(7) C19 C9 C27 O6 44.6(8) C19 C10 C11 C12 -1.7(9) C19 C10 C30 O7 36.5(9) C19 C10 C30 O8 -148.0(6) C19 C15 C16 C12 3.5(8) C19 C15 C16 C17 -176.3(5) C20 C3 C21 O1 -148.1(6) C20 C3 C21 O2 38.2(8) C20 C4 C5 C6 -1.2(9) C20 C4 C24 O3 31.0(9) C20 C4 C24 O4 -150.7(6) C21 O2 C22 C23 -176.2(6) C21 C3 C20 C4 15.7(9) C21 C3 C20 C18 -163.0(6) C22 O2 C21 O1 7.4(9) C22 O2 C21 C3 -178.7(5) C24 O4 C25 C26 -177.0(6) C24 C4 C5 C6 169.7(6) C24 C4 C20 C3 19.6(9) C24 C4 C20 C18 -161.6(5) C25 O4 C24 O3 4.5(9) C25 O4 C24 C4 -173.8(5) C27 O6 C28 C29 -172.6(6) C27 C9 C19 C10 10.2(9) C27 C9 C19 C15 -168.2(6) C28 O6 C27 O5 7.0(9) C28 O6 C27 C9 -179.0(5) C30 O8 C31 C32 -179.5(7) C30 C10 C11 C12 169.7(6) C30 C10 C19 C9 17.5(9) C30 C10 C19 C15 -164.2(5) C31 O8 C30 O7 4.2(10) C31 O8 C30 C10 -171.4(6)