#------------------------------------------------------------------------------ #$Date: 2021-09-16 03:21:09 +0300 (Thu, 16 Sep 2021) $ #$Revision: 269159 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158300.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_7158300 loop_ _publ_author_name 'Wang, Rui-Li' 'Jia, Shi-Kun' 'Guo, Ya-Jun' 'Yi, Yang' 'Hua, Yuan-Zhao' 'Lu, Huijie' 'Wang, Mincan' _publ_section_title ; Dinuclear Zinc-Catalyzed Enantioselective Formal [3+2] Cycloaddition of N-2,2,2-Trifluoroethylisatin Ketimines with Low Reactive Aurone Derivatives ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01599K _journal_year 2021 _chemical_formula_sum 'C29 H24 Br F3 N2 O5' _chemical_formula_weight 617.41 _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_Hall 'P 1' _space_group_name_H-M_alt 'P 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2020-11-02 deposited with the CCDC. 2021-09-14 downloaded from the CCDC. ; _cell_angle_alpha 113.621(8) _cell_angle_beta 101.541(7) _cell_angle_gamma 100.342(7) _cell_formula_units_Z 1 _cell_length_a 7.0824(5) _cell_length_b 9.9984(8) _cell_length_c 11.3089(9) _cell_measurement_temperature 293(2) _cell_volume 688.15(11) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_unetI/netI 0.0616 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 7450 _diffrn_reflns_point_group_measured_fraction_full 0.791 _diffrn_reflns_point_group_measured_fraction_max 0.791 _diffrn_reflns_theta_full 67.108 _diffrn_reflns_theta_max 67.108 _diffrn_reflns_theta_min 4.476 _exptl_absorpt_coefficient_mu 2.584 _exptl_crystal_density_diffrn 1.490 _exptl_crystal_F_000 314 _exptl_crystal_size_max 0.160 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.527 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details ; Flack x determined using 995 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.003(16) _refine_ls_extinction_coef 0.0043(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 372 _refine_ls_number_reflns 3900 _refine_ls_number_restraints 21 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0487 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.0394P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1188 _refine_ls_wR_factor_ref 0.1303 _reflns_Friedel_coverage 0.583 _reflns_Friedel_fraction_full 0.583 _reflns_Friedel_fraction_max 0.583 _reflns_number_gt 3281 _reflns_number_total 3900 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01599k2.cif _cod_data_source_block 202008157 _cod_original_cell_volume 688.15(10) _cod_database_code 7158300 _shelx_shelxl_version_number 2014/7 _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 0.683 _shelx_estimated_absorpt_t_max 0.782 _shelx_res_file ; 202008157.res created by SHELXL-2014/7 TITL 202008157 in P1 #1 REM reset to P1 #1 CELL 1.54184 7.082436 9.998368 11.30887 113.6211 101.5411 100.3417 ZERR 1 0.000546 0.000794 0.000912 0.0077 0.0068 0.0066 LATT -1 SFAC C H Br F N O UNIT 29 24 1 3 2 5 EQIV $1 -1+X,+Y,+Z DFIX 0.87 N2 H2 DFIX 1.63 C29 C28 DFIX 0.87 N1 H1 DFIX 1.45 C28 O5 DFIX 1.55 O5 C26 DFIX 1.53 C27 C26 ISOR 0.01 0.02 C27 C26 L.S. 4 0 0 PLAN 20 SIZE 0.16 0.14 0.1 MPLA C1 C2 N1 C3 C4 C5 C6 C7 C8 MPLA C2 C9 C18 N2 MPLA C17 C18 C9 MPLA C9 C10 C11 C12 C13 C14 C15 C16 O3 MPLA C20 C21 C22 C23 C24 C25 HTAB N1 O4 HTAB N2 O4_$1 bond $h conf fmap 2 acta REM REM REM WGHT 0.064300 0.039400 EXTI 0.004299 FVAR 12.23611 BR1 3 -0.078910 -0.209140 0.795190 11.00000 0.11780 0.12549 = 0.12136 0.09625 0.07604 0.04785 C1 1 0.700232 0.187246 0.392594 11.00000 0.04033 0.06922 = 0.04683 0.03305 0.02131 0.02129 C2 1 0.504973 0.232769 0.411506 11.00000 0.03160 0.04180 = 0.04042 0.02100 0.01117 0.00671 C3 1 0.548530 0.386833 0.410803 11.00000 0.04242 0.04057 = 0.04464 0.02250 0.00982 0.00266 C4 1 0.735515 0.419863 0.394901 11.00000 0.05386 0.06119 = 0.05764 0.03133 0.02076 0.00690 C5 1 0.811016 0.548945 0.380265 11.00000 0.07785 0.06469 = 0.09066 0.04214 0.03650 0.00346 AFIX 43 H5 2 0.938927 0.571639 0.371174 11.00000 -1.20000 AFIX 0 C6 1 0.688498 0.642243 0.379754 11.00000 0.12154 0.04508 = 0.07777 0.02979 0.03413 -0.00266 AFIX 43 H6 2 0.733577 0.727945 0.367916 11.00000 -1.20000 AFIX 0 C7 1 0.501924 0.610563 0.396385 11.00000 0.09209 0.04708 = 0.07023 0.03026 0.02376 0.02276 AFIX 43 H7 2 0.422758 0.675408 0.396489 11.00000 -1.20000 AFIX 0 C8 1 0.429957 0.482955 0.413048 11.00000 0.06121 0.04817 = 0.06036 0.02879 0.01986 0.01788 AFIX 43 H8 2 0.304063 0.462401 0.425521 11.00000 -1.20000 AFIX 0 C9 1 0.457205 0.226164 0.537170 11.00000 0.03299 0.04285 = 0.03535 0.01884 0.01222 0.01285 C10 1 0.633862 0.306301 0.670442 11.00000 0.03485 0.04996 = 0.04674 0.02376 0.00779 0.00898 C11 1 0.568895 0.421569 0.764474 11.00000 0.04536 0.04598 = 0.04386 0.02094 0.01187 0.00790 C12 1 0.377498 0.414452 0.697113 11.00000 0.04216 0.03514 = 0.03839 0.01553 0.01680 0.00375 C13 1 0.270141 0.509921 0.759461 11.00000 0.05931 0.05499 = 0.05973 0.02829 0.03058 0.02528 AFIX 43 H13 2 0.141291 0.503608 0.714257 11.00000 -1.20000 AFIX 0 C14 1 0.366085 0.614441 0.892231 11.00000 0.08727 0.06202 = 0.05610 0.01366 0.03392 0.02538 AFIX 43 H14 2 0.299299 0.681076 0.937301 11.00000 -1.20000 AFIX 0 C15 1 0.555856 0.625576 0.961910 11.00000 0.08890 0.06968 = 0.04897 0.00889 0.02130 0.01545 AFIX 43 H15 2 0.613465 0.698438 1.051833 11.00000 -1.20000 AFIX 0 C16 1 0.661980 0.529231 0.899355 11.00000 0.06114 0.07005 = 0.04212 0.01754 0.00305 0.00693 AFIX 43 H16 2 0.790498 0.536070 0.945557 11.00000 -1.20000 AFIX 0 C17 1 0.361299 0.055212 0.483408 11.00000 0.03817 0.04122 = 0.03969 0.01967 0.01390 0.01466 AFIX 13 H17 2 0.467436 0.005116 0.469352 11.00000 -1.20000 AFIX 0 C18 1 0.223451 0.016814 0.341483 11.00000 0.03619 0.04018 = 0.03555 0.01659 0.00790 0.00548 AFIX 13 H18 2 0.096521 0.039743 0.349870 11.00000 -1.20000 AFIX 0 C19 1 0.179618 -0.147900 0.239804 11.00000 0.05946 0.04629 = 0.04079 0.01599 0.01171 0.00337 C20 1 0.260227 0.004991 0.570182 11.00000 0.04168 0.03455 = 0.03659 0.01655 0.01256 0.01147 C21 1 0.340587 -0.083868 0.623243 11.00000 0.05434 0.05478 = 0.05141 0.03155 0.01985 0.02130 AFIX 43 H21 2 0.461125 -0.102777 0.611593 11.00000 -1.20000 AFIX 0 C22 1 0.242805 -0.144304 0.693138 11.00000 0.07638 0.06487 = 0.06203 0.04541 0.03380 0.03487 AFIX 43 H22 2 0.296047 -0.204549 0.727371 11.00000 -1.20000 AFIX 0 C23 1 0.066207 -0.113996 0.711149 11.00000 0.07057 0.05774 = 0.05282 0.03552 0.02775 0.01561 C24 1 -0.013927 -0.022882 0.664881 11.00000 0.04676 0.07006 = 0.05703 0.03595 0.02598 0.02166 AFIX 43 H24 2 -0.131646 -0.001255 0.680289 11.00000 -1.20000 AFIX 0 C25 1 0.084449 0.036327 0.594587 11.00000 0.04394 0.05656 = 0.04645 0.03165 0.01967 0.01931 AFIX 43 H25 2 0.031582 0.098606 0.562924 11.00000 -1.20000 AFIX 0 F1 4 0.340925 -0.192672 0.221772 11.00000 0.09452 0.05826 = 0.07068 0.01967 0.03634 0.03238 F2 4 0.075323 -0.243842 0.273792 11.00000 0.11948 0.05166 = 0.07418 0.02751 0.03985 -0.00475 F3 4 0.069790 -0.172831 0.117682 11.00000 0.09563 0.06749 = 0.04447 0.01499 -0.00393 0.00010 N1 5 0.825629 0.305779 0.392343 11.00000 0.04275 0.06973 = 0.08754 0.04052 0.03212 0.01687 H1 2 0.924198 0.287044 0.360793 11.00000 0.04195 N2 5 0.333092 0.118212 0.298389 11.00000 0.03658 0.04015 = 0.03819 0.02056 0.00740 0.00739 H2 2 0.262403 0.161676 0.264314 11.00000 0.03573 O1 6 0.730289 0.066218 0.373188 11.00000 0.05442 0.06989 = 0.07184 0.03972 0.02823 0.03209 O2 6 0.788207 0.270076 0.683146 11.00000 0.04412 0.07916 = 0.05694 0.02983 0.00551 0.02333 O3 6 0.305379 0.305259 0.565216 11.00000 0.03448 0.04318 = 0.04222 0.01898 0.01101 0.01447 C26 1 0.893698 0.184209 0.074073 11.00000 0.13889 0.13866 = 0.11301 0.04077 0.02600 0.07359 C27 1 0.676629 0.073333 0.016428 11.00000 0.10800 0.19865 = 0.13392 0.03503 0.03790 0.01307 AFIX 137 H27A 2 0.580901 0.130849 0.023481 11.00000 -1.50000 H27B 2 0.662873 0.016728 0.067152 11.00000 -1.50000 H27C 2 0.652307 0.004075 -0.076885 11.00000 -1.50000 AFIX 0 C28 1 1.097068 0.344260 0.016112 11.00000 0.17959 0.22712 = 0.14614 0.13019 0.02446 0.02314 AFIX 23 H28A 2 1.122061 0.421121 0.108099 11.00000 -1.20000 H28B 2 1.082016 0.393476 -0.042294 11.00000 -1.20000 AFIX 0 C29 1 1.281005 0.283328 0.008076 11.00000 0.23599 0.18453 = 0.14473 0.04589 0.03040 -0.02663 AFIX 137 H29A 2 1.395633 0.354973 0.083209 11.00000 -1.50000 H29B 2 1.308697 0.269623 -0.075071 11.00000 -1.50000 H29C 2 1.253518 0.187347 0.011072 11.00000 -1.50000 AFIX 0 O4 6 1.016798 0.238072 0.177883 11.00000 0.06235 0.14721 = 0.06057 0.04876 0.01138 0.03575 O5 6 0.902432 0.223632 -0.024055 11.00000 0.21723 0.20524 = 0.09253 0.09160 0.03484 0.08538 HKLF 4 REM 202008157 in P1 #1 REM R1 = 0.0487 for 3281 Fo > 4sig(Fo) and 0.0595 for all 3900 data REM 372 parameters refined using 21 restraints END WGHT 0.0643 0.0394 REM Highest difference peak 0.527, deepest hole -0.366, 1-sigma level 0.053 Q1 1 0.0549 -0.1198 0.8729 11.00000 0.05 0.53 Q2 1 1.0264 0.2645 0.0716 11.00000 0.05 0.42 Q3 1 0.6652 0.1946 0.0198 11.00000 0.05 0.27 Q4 1 -0.0073 -0.1935 0.7401 11.00000 0.05 0.26 Q5 1 0.7590 0.2182 0.0226 11.00000 0.05 0.23 Q6 1 0.3829 0.5042 0.6938 11.00000 0.05 0.19 Q7 1 0.4906 0.0902 -0.0161 11.00000 0.05 0.19 Q8 1 0.5470 0.0657 0.0408 11.00000 0.05 0.18 Q9 1 1.1122 0.2827 0.4122 11.00000 0.05 0.18 Q10 1 1.4679 0.5149 0.1062 11.00000 0.05 0.17 Q11 1 0.6254 -0.0163 0.3017 11.00000 0.05 0.17 Q12 1 0.8396 0.3428 0.5399 11.00000 0.05 0.17 Q13 1 -0.1775 -0.0936 0.5774 11.00000 0.05 0.17 Q14 1 0.8973 0.2158 0.7447 11.00000 0.05 0.17 Q15 1 0.2067 0.7817 0.8878 11.00000 0.05 0.17 Q16 1 0.1146 0.4408 0.6766 11.00000 0.05 0.16 Q17 1 0.2638 -0.0238 0.3992 11.00000 0.05 0.16 Q18 1 0.7860 0.1313 -0.0371 11.00000 0.05 0.16 Q19 1 0.7289 0.6594 1.1064 11.00000 0.05 0.16 Q20 1 0.1424 0.3173 0.7240 11.00000 0.05 0.16 ; _shelx_res_checksum 8266 loop_ _space_group_symop_operation_xyz 'x, y, 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 -0.07891(12) -0.20914(10) 0.79519(10) 0.0991(5) Uani 1 1 d . . . . . C1 C 0.7002(10) 0.1872(9) 0.3926(7) 0.0476(15) Uani 1 1 d . . . . . C2 C 0.5050(8) 0.2328(7) 0.4115(6) 0.0376(12) Uani 1 1 d . . . . . C3 C 0.5485(10) 0.3868(7) 0.4108(7) 0.0433(14) Uani 1 1 d . . . . . C4 C 0.7355(11) 0.4199(9) 0.3949(8) 0.0568(18) Uani 1 1 d . . . . . C5 C 0.8110(15) 0.5489(10) 0.3803(10) 0.076(2) Uani 1 1 d . . . . . H5 H 0.9389 0.5716 0.3712 0.091 Uiso 1 1 calc R U . . . C6 C 0.6885(17) 0.6422(9) 0.3798(10) 0.084(3) Uani 1 1 d . . . . . H6 H 0.7336 0.7279 0.3679 0.101 Uiso 1 1 calc R U . . . C7 C 0.5019(14) 0.6106(9) 0.3964(9) 0.068(2) Uani 1 1 d . . . . . H7 H 0.4228 0.6754 0.3965 0.082 Uiso 1 1 calc R U . . . C8 C 0.4300(12) 0.4830(8) 0.4130(8) 0.0546(17) Uani 1 1 d . . . . . H8 H 0.3041 0.4624 0.4255 0.065 Uiso 1 1 calc R U . . . C9 C 0.4572(8) 0.2262(7) 0.5372(6) 0.0361(12) Uani 1 1 d . . . . . C10 C 0.6339(9) 0.3063(7) 0.6704(7) 0.0444(14) Uani 1 1 d . . . . . C11 C 0.5689(10) 0.4216(7) 0.7645(7) 0.0459(14) Uani 1 1 d . . . . . C12 C 0.3775(9) 0.4145(7) 0.6971(6) 0.0393(13) Uani 1 1 d . . . . . C13 C 0.2701(11) 0.5099(8) 0.7595(8) 0.0539(17) Uani 1 1 d . . . . . H13 H 0.1413 0.5036 0.7143 0.065 Uiso 1 1 calc R U . . . C14 C 0.3661(15) 0.6144(10) 0.8922(9) 0.070(2) Uani 1 1 d . . . . . H14 H 0.2993 0.6811 0.9373 0.085 Uiso 1 1 calc R U . . . C15 C 0.5559(16) 0.6256(11) 0.9619(9) 0.076(3) Uani 1 1 d . . . . . H15 H 0.6135 0.6984 1.0518 0.092 Uiso 1 1 calc R U . . . C16 C 0.6620(13) 0.5292(10) 0.8994(8) 0.064(2) Uani 1 1 d . . . . . H16 H 0.7905 0.5361 0.9456 0.077 Uiso 1 1 calc R U . . . C17 C 0.3613(9) 0.0552(7) 0.4834(6) 0.0384(13) Uani 1 1 d . . . . . H17 H 0.4674 0.0051 0.4694 0.046 Uiso 1 1 calc R U . . . C18 C 0.2235(9) 0.0168(7) 0.3415(6) 0.0388(13) Uani 1 1 d . . . . . H18 H 0.0965 0.0397 0.3499 0.047 Uiso 1 1 calc R U . . . C19 C 0.1796(11) -0.1479(8) 0.2398(7) 0.0524(16) Uani 1 1 d . . . . . C20 C 0.2602(9) 0.0050(7) 0.5702(6) 0.0373(12) Uani 1 1 d . . . . . C21 C 0.3406(11) -0.0839(8) 0.6232(7) 0.0495(16) Uani 1 1 d . . . . . H21 H 0.4611 -0.1028 0.6116 0.059 Uiso 1 1 calc R U . . . C22 C 0.2428(12) -0.1443(9) 0.6931(8) 0.0577(18) Uani 1 1 d . . . . . H22 H 0.2960 -0.2045 0.7274 0.069 Uiso 1 1 calc R U . . . C23 C 0.0662(12) -0.1140(8) 0.7111(7) 0.0557(18) Uani 1 1 d . . . . . C24 C -0.0139(11) -0.0229(9) 0.6649(8) 0.0531(17) Uani 1 1 d . . . . . H24 H -0.1316 -0.0013 0.6803 0.064 Uiso 1 1 calc R U . . . C25 C 0.0844(9) 0.0363(8) 0.5946(7) 0.0444(14) Uani 1 1 d . . . . . H25 H 0.0316 0.0986 0.5629 0.053 Uiso 1 1 calc R U . . . F1 F 0.3409(8) -0.1927(5) 0.2218(5) 0.0745(13) Uani 1 1 d . . . . . F2 F 0.0753(9) -0.2438(5) 0.2738(5) 0.0847(16) Uani 1 1 d . . . . . F3 F 0.0698(8) -0.1728(5) 0.1177(5) 0.0803(14) Uani 1 1 d . . . . . N1 N 0.8256(10) 0.3058(8) 0.3923(8) 0.0628(17) Uani 1 1 d D . . . . H1 H 0.924(7) 0.287(7) 0.361(6) 0.042(18) Uiso 1 1 d D . . . . N2 N 0.3331(7) 0.1182(6) 0.2984(5) 0.0385(11) Uani 1 1 d D . . . . H2 H 0.262(8) 0.162(7) 0.264(6) 0.036(16) Uiso 1 1 d D . . . . O1 O 0.7303(7) 0.0662(6) 0.3732(5) 0.0592(13) Uani 1 1 d . . . . . O2 O 0.7882(7) 0.2701(6) 0.6831(5) 0.0612(13) Uani 1 1 d . . . . . O3 O 0.3054(6) 0.3053(5) 0.5652(4) 0.0397(9) Uani 1 1 d . . . . . C26 C 0.894(2) 0.1842(18) 0.0741(16) 0.133(5) Uani 1 1 d D U . . . C27 C 0.677(2) 0.073(2) 0.0164(18) 0.165(7) Uani 1 1 d D U . . . H27A H 0.5809 0.1308 0.0235 0.248 Uiso 1 1 calc R U . . . H27B H 0.6629 0.0167 0.0672 0.248 Uiso 1 1 calc R U . . . H27C H 0.6523 0.0041 -0.0769 0.248 Uiso 1 1 calc R U . . . C28 C 1.097(3) 0.344(3) 0.016(2) 0.178(9) Uani 1 1 d D . . . . H28A H 1.1221 0.4211 0.1081 0.213 Uiso 1 1 calc R U . . . H28B H 1.0820 0.3935 -0.0423 0.213 Uiso 1 1 calc R U . . . C29 C 1.281(4) 0.283(3) 0.008(2) 0.216(11) Uani 1 1 d D . . . . H29A H 1.3956 0.3550 0.0832 0.323 Uiso 1 1 calc R U . . . H29B H 1.3087 0.2696 -0.0751 0.323 Uiso 1 1 calc R U . . . H29C H 1.2535 0.1873 0.0111 0.323 Uiso 1 1 calc R U . . . O4 O 1.0168(10) 0.2381(10) 0.1779(7) 0.090(2) Uani 1 1 d . . . . . O5 O 0.902(2) 0.2236(16) -0.0241(10) 0.162(5) Uani 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 0.1178(9) 0.1255(9) 0.1214(9) 0.0962(8) 0.0760(7) 0.0479(7) C1 0.040(3) 0.069(4) 0.047(4) 0.033(3) 0.021(3) 0.021(3) C2 0.032(3) 0.042(3) 0.040(3) 0.021(3) 0.011(2) 0.007(2) C3 0.042(3) 0.041(3) 0.045(3) 0.022(3) 0.010(3) 0.003(3) C4 0.054(4) 0.061(4) 0.058(4) 0.031(4) 0.021(3) 0.007(3) C5 0.078(6) 0.065(5) 0.091(7) 0.042(5) 0.036(5) 0.003(4) C6 0.122(8) 0.045(4) 0.078(6) 0.030(4) 0.034(6) -0.003(5) C7 0.092(6) 0.047(4) 0.070(5) 0.030(4) 0.024(5) 0.023(4) C8 0.061(4) 0.048(4) 0.060(4) 0.029(3) 0.020(4) 0.018(3) C9 0.033(3) 0.043(3) 0.035(3) 0.019(3) 0.012(2) 0.013(2) C10 0.035(3) 0.050(4) 0.047(4) 0.024(3) 0.008(3) 0.009(3) C11 0.045(4) 0.046(3) 0.044(4) 0.021(3) 0.012(3) 0.008(3) C12 0.042(3) 0.035(3) 0.038(3) 0.016(3) 0.017(3) 0.004(3) C13 0.059(4) 0.055(4) 0.060(4) 0.028(4) 0.031(3) 0.025(3) C14 0.087(6) 0.062(5) 0.056(5) 0.014(4) 0.034(5) 0.025(4) C15 0.089(7) 0.070(5) 0.049(5) 0.009(4) 0.021(5) 0.015(5) C16 0.061(5) 0.070(5) 0.042(4) 0.018(4) 0.003(4) 0.007(4) C17 0.038(3) 0.041(3) 0.040(3) 0.020(3) 0.014(3) 0.015(3) C18 0.036(3) 0.040(3) 0.036(3) 0.017(3) 0.008(2) 0.005(2) C19 0.059(4) 0.046(4) 0.041(4) 0.016(3) 0.012(3) 0.003(3) C20 0.042(3) 0.035(3) 0.037(3) 0.017(3) 0.013(2) 0.011(2) C21 0.054(4) 0.055(4) 0.051(4) 0.032(3) 0.020(3) 0.021(3) C22 0.076(5) 0.065(4) 0.062(5) 0.045(4) 0.034(4) 0.035(4) C23 0.071(5) 0.058(4) 0.053(4) 0.036(4) 0.028(4) 0.016(4) C24 0.047(4) 0.070(5) 0.057(4) 0.036(4) 0.026(3) 0.022(3) C25 0.044(4) 0.057(4) 0.046(4) 0.032(3) 0.020(3) 0.019(3) F1 0.095(4) 0.058(2) 0.071(3) 0.020(2) 0.036(3) 0.032(2) F2 0.119(4) 0.052(2) 0.074(3) 0.028(2) 0.040(3) -0.005(3) F3 0.096(4) 0.067(3) 0.044(2) 0.015(2) -0.004(2) 0.000(3) N1 0.043(3) 0.070(4) 0.088(5) 0.041(4) 0.032(3) 0.017(3) N2 0.037(3) 0.040(3) 0.038(3) 0.021(2) 0.007(2) 0.007(2) O1 0.054(3) 0.070(3) 0.072(4) 0.040(3) 0.028(3) 0.032(3) O2 0.044(3) 0.079(3) 0.057(3) 0.030(3) 0.006(2) 0.023(2) O3 0.034(2) 0.043(2) 0.042(2) 0.019(2) 0.0110(18) 0.0145(17) C26 0.139(10) 0.139(9) 0.113(9) 0.041(7) 0.026(7) 0.074(8) C27 0.108(11) 0.199(16) 0.134(12) 0.035(11) 0.038(9) 0.013(10) C28 0.18(2) 0.23(3) 0.146(17) 0.130(19) 0.024(16) 0.023(19) C29 0.24(3) 0.18(2) 0.145(19) 0.046(16) 0.030(19) -0.027(19) O4 0.062(4) 0.147(7) 0.061(4) 0.049(4) 0.011(3) 0.036(4) O5 0.217(13) 0.205(12) 0.093(7) 0.092(8) 0.035(8) 0.085(11) 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 O1 C1 N1 125.9(6) . . ? O1 C1 C2 127.1(6) . . ? N1 C1 C2 106.8(6) . . ? N2 C2 C3 113.0(5) . . ? N2 C2 C9 103.7(4) . . ? C3 C2 C9 117.5(5) . . ? N2 C2 C1 108.8(5) . . ? C3 C2 C1 101.8(5) . . ? C9 C2 C1 112.1(5) . . ? C4 C3 C8 120.1(6) . . ? C4 C3 C2 108.4(6) . . ? C8 C3 C2 131.3(6) . . ? C3 C4 C5 121.7(8) . . ? C3 C4 N1 110.1(6) . . ? C5 C4 N1 128.1(7) . . ? C6 C5 C4 117.5(8) . . ? C6 C5 H5 121.3 . . ? C4 C5 H5 121.3 . . ? C7 C6 C5 121.2(7) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 120.7(8) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C3 C8 C7 118.8(7) . . ? C3 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? O3 C9 C17 109.0(4) . . ? O3 C9 C10 105.2(5) . . ? C17 C9 C10 116.9(5) . . ? O3 C9 C2 107.6(4) . . ? C17 C9 C2 101.6(5) . . ? C10 C9 C2 116.2(5) . . ? O2 C10 C11 131.4(6) . . ? O2 C10 C9 123.1(6) . . ? C11 C10 C9 105.4(5) . . ? C12 C11 C16 120.2(7) . . ? C12 C11 C10 107.6(6) . . ? C16 C11 C10 132.2(7) . . ? O3 C12 C13 123.4(6) . . ? O3 C12 C11 114.1(5) . . ? C13 C12 C11 122.5(6) . . ? C14 C13 C12 115.8(7) . . ? C14 C13 H13 122.1 . . ? C12 C13 H13 122.1 . . ? C13 C14 C15 123.4(8) . . ? C13 C14 H14 118.3 . . ? C15 C14 H14 118.3 . . ? C14 C15 C16 120.6(8) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 117.5(8) . . ? C15 C16 H16 121.2 . . ? C11 C16 H16 121.2 . . ? C20 C17 C9 117.5(5) . . ? C20 C17 C18 116.1(5) . . ? C9 C17 C18 100.1(4) . . ? C20 C17 H17 107.5 . . ? C9 C17 H17 107.5 . . ? C18 C17 H17 107.5 . . ? N2 C18 C19 110.4(5) . . ? N2 C18 C17 105.2(4) . . ? C19 C18 C17 112.8(5) . . ? N2 C18 H18 109.4 . . ? C19 C18 H18 109.4 . . ? C17 C18 H18 109.4 . . ? F1 C19 F2 105.9(6) . . ? F1 C19 F3 106.1(6) . . ? F2 C19 F3 107.0(6) . . ? F1 C19 C18 114.8(6) . . ? F2 C19 C18 112.2(6) . . ? F3 C19 C18 110.3(6) . . ? C25 C20 C21 118.0(6) . . ? C25 C20 C17 123.2(5) . . ? C21 C20 C17 118.7(6) . . ? C22 C21 C20 120.7(7) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C23 C22 C21 119.1(6) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C24 C23 C22 122.0(6) . . ? C24 C23 Br1 118.8(6) . . ? C22 C23 Br1 119.2(5) . . ? C23 C24 C25 118.4(6) . . ? C23 C24 H24 120.8 . . ? C25 C24 H24 120.8 . . ? C24 C25 C20 121.7(6) . . ? C24 C25 H25 119.2 . . ? C20 C25 H25 119.2 . . ? C1 N1 C4 112.5(6) . . ? C1 N1 H1 116(5) . . ? C4 N1 H1 127(5) . . ? C2 N2 C18 109.9(4) . . ? C2 N2 H2 110(4) . . ? C18 N2 H2 115(4) . . ? C12 O3 C9 107.6(4) . . ? O4 C26 O5 124.5(16) . . ? O4 C26 C27 133.5(16) . . ? O5 C26 C27 101.5(15) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O5 C28 C29 114.2(18) . . ? O5 C28 H28A 108.7 . . ? C29 C28 H28A 108.7 . . ? O5 C28 H28B 108.7 . . ? C29 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 O5 C28 110.8(13) . . ? 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 C23 1.905(7) . ? C1 O1 1.207(8) . ? C1 N1 1.349(9) . ? C1 C2 1.559(8) . ? C2 N2 1.460(8) . ? C2 C3 1.519(8) . ? C2 C9 1.549(8) . ? C3 C4 1.372(10) . ? C3 C8 1.381(10) . ? C4 C5 1.392(11) . ? C4 N1 1.397(11) . ? C5 C6 1.384(14) . ? C5 H5 0.9300 . ? C6 C7 1.371(13) . ? C6 H6 0.9300 . ? C7 C8 1.386(10) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 O3 1.457(7) . ? C9 C17 1.529(8) . ? C9 C10 1.548(8) . ? C10 O2 1.212(8) . ? C10 C11 1.440(10) . ? C11 C12 1.390(9) . ? C11 C16 1.395(10) . ? C12 O3 1.367(7) . ? C12 C13 1.386(9) . ? C13 C14 1.374(11) . ? C13 H13 0.9300 . ? C14 C15 1.375(14) . ? C14 H14 0.9300 . ? C15 C16 1.386(13) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C20 1.508(8) . ? C17 C18 1.556(8) . ? C17 H17 0.9800 . ? C18 N2 1.460(7) . ? C18 C19 1.512(9) . ? C18 H18 0.9800 . ? C19 F1 1.323(9) . ? C19 F2 1.330(8) . ? C19 F3 1.341(8) . ? C20 C25 1.390(9) . ? C20 C21 1.395(9) . ? C21 C22 1.386(10) . ? C21 H21 0.9300 . ? C22 C23 1.373(11) . ? C22 H22 0.9300 . ? C23 C24 1.369(10) . ? C24 C25 1.385(9) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? N1 H1 0.86(3) . ? N2 H2 0.85(3) . ? C26 O4 1.159(16) . ? C26 O5 1.327(16) . ? C26 C27 1.557(18) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 O5 1.508(17) . ? C28 C29 1.54(2) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? 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 N1 H1 O4 0.86(3) 2.19(5) 2.916(9) 142(6) . N2 H2 O4 0.85(3) 2.23(3) 3.060(8) 166(6) 1_455 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 O1 C1 C2 N2 -52.5(8) . . . . ? N1 C1 C2 N2 123.2(6) . . . . ? O1 C1 C2 C3 -172.0(7) . . . . ? N1 C1 C2 C3 3.7(7) . . . . ? O1 C1 C2 C9 61.6(9) . . . . ? N1 C1 C2 C9 -122.7(6) . . . . ? N2 C2 C3 C4 -116.7(6) . . . . ? C9 C2 C3 C4 122.5(6) . . . . ? C1 C2 C3 C4 -0.2(7) . . . . ? N2 C2 C3 C8 57.9(10) . . . . ? C9 C2 C3 C8 -62.9(9) . . . . ? C1 C2 C3 C8 174.4(7) . . . . ? C8 C3 C4 C5 -0.2(12) . . . . ? C2 C3 C4 C5 175.1(8) . . . . ? C8 C3 C4 N1 -178.6(7) . . . . ? C2 C3 C4 N1 -3.2(9) . . . . ? C3 C4 C5 C6 -1.2(14) . . . . ? N1 C4 C5 C6 176.8(9) . . . . ? C4 C5 C6 C7 1.6(15) . . . . ? C5 C6 C7 C8 -0.6(15) . . . . ? C4 C3 C8 C7 1.2(11) . . . . ? C2 C3 C8 C7 -172.9(7) . . . . ? C6 C7 C8 C3 -0.9(12) . . . . ? N2 C2 C9 O3 -76.6(5) . . . . ? C3 C2 C9 O3 48.8(7) . . . . ? C1 C2 C9 O3 166.2(5) . . . . ? N2 C2 C9 C17 37.8(5) . . . . ? C3 C2 C9 C17 163.3(5) . . . . ? C1 C2 C9 C17 -79.4(6) . . . . ? N2 C2 C9 C10 165.8(5) . . . . ? C3 C2 C9 C10 -68.7(7) . . . . ? C1 C2 C9 C10 48.6(7) . . . . ? O3 C9 C10 O2 -179.4(6) . . . . ? C17 C9 C10 O2 59.6(8) . . . . ? C2 C9 C10 O2 -60.5(8) . . . . ? O3 C9 C10 C11 1.2(6) . . . . ? C17 C9 C10 C11 -119.8(6) . . . . ? C2 C9 C10 C11 120.1(6) . . . . ? O2 C10 C11 C12 -180.0(7) . . . . ? C9 C10 C11 C12 -0.6(7) . . . . ? O2 C10 C11 C16 0.7(13) . . . . ? C9 C10 C11 C16 -180.0(7) . . . . ? C16 C11 C12 O3 179.2(6) . . . . ? C10 C11 C12 O3 -0.3(7) . . . . ? C16 C11 C12 C13 -1.1(10) . . . . ? C10 C11 C12 C13 179.5(6) . . . . ? O3 C12 C13 C14 -179.3(6) . . . . ? C11 C12 C13 C14 1.0(10) . . . . ? C12 C13 C14 C15 -0.5(12) . . . . ? C13 C14 C15 C16 0.1(15) . . . . ? C14 C15 C16 C11 -0.2(14) . . . . ? C12 C11 C16 C15 0.6(11) . . . . ? C10 C11 C16 C15 179.9(8) . . . . ? O3 C9 C17 C20 -56.1(6) . . . . ? C10 C9 C17 C20 62.9(7) . . . . ? C2 C9 C17 C20 -169.5(5) . . . . ? O3 C9 C17 C18 70.5(5) . . . . ? C10 C9 C17 C18 -170.5(5) . . . . ? C2 C9 C17 C18 -43.0(5) . . . . ? C20 C17 C18 N2 161.2(5) . . . . ? C9 C17 C18 N2 33.7(6) . . . . ? C20 C17 C18 C19 -78.4(7) . . . . ? C9 C17 C18 C19 154.1(5) . . . . ? N2 C18 C19 F1 60.6(7) . . . . ? C17 C18 C19 F1 -56.9(7) . . . . ? N2 C18 C19 F2 -178.4(6) . . . . ? C17 C18 C19 F2 64.2(8) . . . . ? N2 C18 C19 F3 -59.2(7) . . . . ? C17 C18 C19 F3 -176.6(6) . . . . ? C9 C17 C20 C25 68.2(8) . . . . ? C18 C17 C20 C25 -50.2(8) . . . . ? C9 C17 C20 C21 -115.2(6) . . . . ? C18 C17 C20 C21 126.4(6) . . . . ? C25 C20 C21 C22 2.7(10) . . . . ? C17 C20 C21 C22 -174.1(7) . . . . ? C20 C21 C22 C23 -0.8(12) . . . . ? C21 C22 C23 C24 -1.6(12) . . . . ? C21 C22 C23 Br1 175.3(6) . . . . ? C22 C23 C24 C25 1.9(12) . . . . ? Br1 C23 C24 C25 -175.1(6) . . . . ? C23 C24 C25 C20 0.2(11) . . . . ? C21 C20 C25 C24 -2.4(10) . . . . ? C17 C20 C25 C24 174.2(6) . . . . ? O1 C1 N1 C4 169.8(7) . . . . ? C2 C1 N1 C4 -6.0(9) . . . . ? C3 C4 N1 C1 6.1(10) . . . . ? C5 C4 N1 C1 -172.1(8) . . . . ? C3 C2 N2 C18 -145.1(5) . . . . ? C9 C2 N2 C18 -16.8(6) . . . . ? C1 C2 N2 C18 102.7(5) . . . . ? C19 C18 N2 C2 -132.6(5) . . . . ? C17 C18 N2 C2 -10.7(6) . . . . ? C13 C12 O3 C9 -178.6(6) . . . . ? C11 C12 O3 C9 1.1(6) . . . . ? C17 C9 O3 C12 124.7(5) . . . . ? C10 C9 O3 C12 -1.4(6) . . . . ? C2 C9 O3 C12 -125.9(5) . . . . ? O4 C26 O5 C28 2(2) . . . . ? C27 C26 O5 C28 174.8(15) . . . . ? C29 C28 O5 C26 76(2) . . . . ?