#------------------------------------------------------------------------------ #$Date: 2021-08-17 00:58:59 +0300 (Tue, 17 Aug 2021) $ #$Revision: 268087 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/88/7128819.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_7128819 loop_ _publ_author_name 'Cui, Zhaohui' 'Zhang, Kuan' 'Gu, Lijie' 'Bu, Zhanwei' 'Zhao, Junwei' 'Wang, Qi-Lin' _publ_section_title ; Diastereoselective trifunctionalization of pyridinium salts to access structurally crowded azaheteropolycycles ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D1CC03478B _journal_year 2021 _chemical_formula_moiety 'C26 H26 Br N3 O7' _chemical_formula_sum 'C26 H26 Br N3 O7' _chemical_formula_weight 572.41 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2020-09-15 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-06-19 deposited with the CCDC. 2021-08-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.088(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.194(5) _cell_length_b 12.288(3) _cell_length_c 18.063(6) _cell_measurement_reflns_used 9978 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 28.140 _cell_measurement_theta_min 2.813 _cell_volume 2474.8(15) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 149.99 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker AXS area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_unetI/netI 0.0294 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 30412 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.368 _diffrn_reflns_theta_min 2.233 _exptl_absorpt_coefficient_mu 1.714 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6695 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0866 before and 0.0600 after correction. The Ratio of minimum to maximum transmission is 0.8978. The \l/2 correction factor is Not present.' _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.536 _exptl_crystal_description block _exptl_crystal_F_000 1176 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.286 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 340 _refine_ls_number_reflns 5059 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0263 _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^)+(0.0222P)^2^+1.3889P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.0603 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4318 _reflns_number_total 5059 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc03478b2.cif _cod_data_source_block m4278_0m _cod_original_cell_volume 2474.7(16) _cod_database_code 7128819 _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_max 0.821 _shelx_estimated_absorpt_t_min 0.715 _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: C7(H7), C15(H15), C16(H16), C17(H17) 2.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C13(H13A,H13B), C20(H20A,H20B) 2.c Aromatic/amide H refined with riding coordinates: C1(H1), C3(H3), C4(H4), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26) 2.d Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C14(H14A,H14B,H14C) ; _shelx_res_file ; m4278_0m.res created by SHELXL-2014/7 TITL m4278_0m_a.res in P2(1)/n REM Old TITL Integration of M4278 REM SHELXT solution in P2(1)/n REM R1 0.110, Rweak 0.005, Alpha 0.030, Orientation as input REM Formula found by SHELXT: C36 Br CELL 0.71073 11.1935 12.288 18.063 90 95.088 90 ZERR 4 0.0054 0.0034 0.006 0 0.014 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 104 104 4 12 28 L.S. 23 0 0 PLAN 20 SIZE 0.21 0.15 0.12 TEMP -123.16 MPLA C1 C2 C3 C4 C5 C6 MPLA C21 C22 C23 C24 C25 C26 htab list 4 bond $h conf fmap 2 acta SHEL 999 0.8 REM REM REM WGHT 0.022200 1.388900 FVAR 0.44854 BR1 3 1.021984 0.355247 0.438657 11.00000 0.02281 0.01942 = 0.02454 0.00253 0.00152 0.00308 C1 1 0.911440 0.541487 0.366291 11.00000 0.01842 0.01907 = 0.01663 -0.00333 0.00377 -0.00187 AFIX 43 H1 2 0.988765 0.555311 0.350550 11.00000 -1.20000 AFIX 0 C2 1 0.891314 0.449724 0.408431 11.00000 0.02195 0.01685 = 0.01797 -0.00298 -0.00081 0.00227 C3 1 0.778855 0.426800 0.431105 11.00000 0.02603 0.01585 = 0.02311 0.00254 0.00306 -0.00163 AFIX 43 H3 2 0.767100 0.364180 0.460437 11.00000 -1.20000 AFIX 0 C4 1 0.683213 0.496258 0.410563 11.00000 0.01861 0.02018 = 0.02467 0.00135 0.00384 -0.00375 AFIX 43 H4 2 0.605238 0.480810 0.424693 11.00000 -1.20000 AFIX 0 C5 1 0.703781 0.588222 0.369185 11.00000 0.01873 0.01618 = 0.01674 -0.00375 0.00020 0.00094 C6 1 0.816978 0.613029 0.347366 11.00000 0.02149 0.01548 = 0.01319 -0.00321 0.00156 -0.00249 C7 1 0.836945 0.723628 0.312364 11.00000 0.01978 0.01692 = 0.01586 -0.00007 0.00553 -0.00212 AFIX 13 H7 2 0.901269 0.717008 0.277582 11.00000 -1.20000 AFIX 0 C8 1 0.772322 0.875134 0.385504 11.00000 0.01867 0.01433 = 0.01747 -0.00069 0.00266 -0.00250 C9 1 0.827864 0.986221 0.410461 11.00000 0.02254 0.01614 = 0.02065 0.00106 0.00117 0.00010 C10 1 0.849889 1.115717 0.507376 11.00000 0.04209 0.02272 = 0.04294 -0.01437 -0.00185 -0.00597 AFIX 23 H10A 2 0.818003 1.176816 0.475808 11.00000 -1.20000 H10B 2 0.938416 1.115505 0.507990 11.00000 -1.20000 AFIX 0 C11 1 0.813457 1.127884 0.584259 11.00000 0.04858 0.05535 = 0.04148 -0.02692 -0.00564 0.00740 AFIX 137 H11A 2 0.725766 1.130419 0.582729 11.00000 -1.50000 H11B 2 0.847166 1.195408 0.606124 11.00000 -1.50000 H11C 2 0.843462 1.065831 0.614518 11.00000 -1.50000 AFIX 0 C12 1 0.703679 0.830824 0.449562 11.00000 0.02049 0.01478 = 0.01713 -0.00059 0.00074 -0.00271 C13 1 0.531011 0.847739 0.516062 11.00000 0.02536 0.02736 = 0.02207 0.00287 0.01088 -0.00088 AFIX 23 H13A 2 0.468556 0.903294 0.522087 11.00000 -1.20000 H13B 2 0.587934 0.848936 0.561247 11.00000 -1.20000 AFIX 0 C14 1 0.472932 0.736700 0.508215 11.00000 0.02644 0.03256 = 0.03851 0.00754 0.00799 -0.00632 AFIX 137 H14A 2 0.418864 0.734383 0.462497 11.00000 -1.50000 H14B 2 0.427177 0.722823 0.551052 11.00000 -1.50000 H14C 2 0.535129 0.680955 0.506012 11.00000 -1.50000 AFIX 0 C15 1 0.615946 0.695674 0.273620 11.00000 0.02214 0.01807 = 0.01583 -0.00006 0.00122 0.00101 AFIX 13 H15 2 0.626808 0.631317 0.241002 11.00000 -1.20000 AFIX 0 C16 1 0.722322 0.772296 0.269740 11.00000 0.02337 0.01620 = 0.01475 0.00058 0.00458 0.00001 AFIX 13 H16 2 0.737248 0.783766 0.216532 11.00000 -1.20000 AFIX 0 C17 1 0.704060 0.884448 0.306832 11.00000 0.02406 0.01486 = 0.01346 0.00148 0.00286 -0.00042 AFIX 13 H17 2 0.748657 0.938985 0.278776 11.00000 -1.20000 AFIX 0 C18 1 0.574565 0.917093 0.297551 11.00000 0.02774 0.01775 = 0.01292 0.00233 0.00184 0.00346 C19 1 0.485103 0.851564 0.267784 11.00000 0.02439 0.02249 = 0.01581 0.00445 0.00161 0.00428 AFIX 43 H19 2 0.406971 0.881419 0.258224 11.00000 -1.20000 AFIX 0 C20 1 0.405629 0.675815 0.216122 11.00000 0.02183 0.02481 = 0.02198 0.00058 -0.00547 -0.00166 AFIX 23 H20A 2 0.431750 0.644902 0.169581 11.00000 -1.20000 H20B 2 0.333357 0.720645 0.202993 11.00000 -1.20000 AFIX 0 C21 1 0.373532 0.583473 0.266748 11.00000 0.01903 0.02826 = 0.01920 -0.00135 -0.00268 -0.00600 C22 1 0.295883 0.602363 0.321182 11.00000 0.02584 0.03610 = 0.03044 -0.00790 0.00402 -0.00631 AFIX 43 H22 2 0.261552 0.672471 0.325803 11.00000 -1.20000 AFIX 0 C23 1 0.268154 0.519372 0.368877 11.00000 0.03175 0.05789 = 0.02590 -0.00419 0.00779 -0.01819 AFIX 43 H23 2 0.215326 0.533185 0.406155 11.00000 -1.20000 AFIX 0 C24 1 0.317001 0.416389 0.362525 11.00000 0.03191 0.04840 = 0.02993 0.01179 -0.00326 -0.01743 AFIX 43 H24 2 0.297627 0.359748 0.395200 11.00000 -1.20000 AFIX 0 C25 1 0.393963 0.396805 0.308384 11.00000 0.03110 0.03004 = 0.04121 0.00772 -0.00300 -0.00628 AFIX 43 H25 2 0.427520 0.326394 0.303694 11.00000 -1.20000 AFIX 0 C26 1 0.422727 0.480426 0.260346 11.00000 0.02330 0.02902 = 0.02631 -0.00096 0.00294 -0.00356 AFIX 43 H26 2 0.475989 0.466665 0.223303 11.00000 -1.20000 AFIX 0 N1 4 0.874012 0.805360 0.370638 11.00000 0.01968 0.01762 = 0.01979 -0.00164 0.00131 -0.00062 H1A 2 0.900951 0.775525 0.410329 11.00000 0.02288 N2 4 0.502196 0.746113 0.251206 11.00000 0.02208 0.01905 = 0.02109 0.00023 -0.00213 -0.00029 N3 4 0.545102 1.026221 0.313852 11.00000 0.03512 0.02026 = 0.01648 0.00168 0.00213 0.00565 O1 5 0.609361 0.658234 0.349744 11.00000 0.01890 0.01905 = 0.01879 0.00236 0.00295 0.00052 O2 5 0.891697 1.038909 0.373906 11.00000 0.03385 0.02159 = 0.02909 0.00108 0.01009 -0.00969 O3 5 0.800917 1.012896 0.478447 11.00000 0.03468 0.01909 = 0.01905 -0.00418 0.00399 -0.00564 O4 5 0.748926 0.766927 0.494777 11.00000 0.02446 0.02135 = 0.02093 0.00639 0.00305 0.00063 O5 5 0.595049 0.875021 0.451289 11.00000 0.02068 0.02111 = 0.01716 0.00346 0.00587 0.00076 O6 5 0.628648 1.086376 0.340190 11.00000 0.03717 0.01780 = 0.02674 -0.00218 -0.00079 -0.00055 O7 5 0.440506 1.060120 0.301831 11.00000 0.03520 0.03323 = 0.04110 -0.00667 -0.00606 0.01683 HKLF 4 REM m4278_0m_a.res in P2(1)/n REM R1 = 0.0263 for 4318 Fo > 4sig(Fo) and 0.0356 for all 5059 data REM 340 parameters refined using 0 restraints END WGHT 0.0222 1.3889 REM Instructions for potential hydrogen bonds HTAB C14 O4 EQIV $1 -x+3/2, y-1/2, -z+1/2 HTAB C15 O2_$1 HTAB C20 O2_$1 HTAB N1 O4 REM Highest difference peak 0.286, deepest hole -0.275, 1-sigma level 0.052 Q1 1 0.8209 0.6693 0.3299 11.00000 0.05 0.29 Q2 1 0.7755 0.7460 0.2934 11.00000 0.05 0.28 Q3 1 0.8018 0.9261 0.3967 11.00000 0.05 0.28 Q4 1 0.3840 0.6199 0.2405 11.00000 0.05 0.27 Q5 1 0.7101 0.8244 0.2904 11.00000 0.05 0.26 Q6 1 0.7373 0.8795 0.3471 11.00000 0.05 0.25 Q7 1 0.6806 0.7282 0.2753 11.00000 0.05 0.24 Q8 1 0.7457 0.8599 0.4160 11.00000 0.05 0.24 Q9 1 0.8334 0.4347 0.4114 11.00000 0.05 0.23 Q10 1 0.5367 0.8795 0.3029 11.00000 0.05 0.23 Q11 1 0.6349 0.9031 0.3030 11.00000 0.05 0.23 Q12 1 0.3100 0.5890 0.2781 11.00000 0.05 0.23 Q13 1 0.6149 0.6791 0.3146 11.00000 0.05 0.23 Q14 1 0.8192 0.8444 0.3815 11.00000 0.05 0.23 Q15 1 0.7617 0.5987 0.3491 11.00000 0.05 0.22 Q16 1 0.3150 0.4814 0.3818 11.00000 0.05 0.22 Q17 1 0.9020 0.5147 0.4037 11.00000 0.05 0.22 Q18 1 0.4603 0.7163 0.2318 11.00000 0.05 0.22 Q19 1 0.6571 0.6184 0.3594 11.00000 0.05 0.22 Q20 1 0.7464 1.1017 0.6018 11.00000 0.05 0.21 ; _shelx_res_checksum 653 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 1.02198(2) 0.35525(2) 0.43866(2) 0.02229(6) Uani 1 1 d . . . . . C1 C 0.91144(16) 0.54149(14) 0.36629(10) 0.0179(4) Uani 1 1 d . . . . . H1 H 0.9888 0.5553 0.3505 0.021 Uiso 1 1 calc R . . . . C2 C 0.89131(16) 0.44972(14) 0.40843(10) 0.0191(4) Uani 1 1 d . . . . . C3 C 0.77885(17) 0.42680(14) 0.43110(10) 0.0216(4) Uani 1 1 d . . . . . H3 H 0.7671 0.3642 0.4604 0.026 Uiso 1 1 calc R . . . . C4 C 0.68321(17) 0.49626(14) 0.41056(10) 0.0210(4) Uani 1 1 d . . . . . H4 H 0.6052 0.4808 0.4247 0.025 Uiso 1 1 calc R . . . . C5 C 0.70378(16) 0.58822(14) 0.36918(10) 0.0173(4) Uani 1 1 d . . . . . C6 C 0.81698(16) 0.61303(13) 0.34737(9) 0.0167(4) Uani 1 1 d . . . . . C7 C 0.83695(16) 0.72363(13) 0.31236(10) 0.0173(4) Uani 1 1 d . . . . . H7 H 0.9013 0.7170 0.2776 0.021 Uiso 1 1 calc R . . . . C8 C 0.77232(16) 0.87513(13) 0.38550(10) 0.0168(4) Uani 1 1 d . . . . . C9 C 0.82786(17) 0.98622(14) 0.41046(10) 0.0198(4) Uani 1 1 d . . . . . C10 C 0.8499(2) 1.11572(16) 0.50738(13) 0.0362(5) Uani 1 1 d . . . . . H10A H 0.8180 1.1768 0.4758 0.043 Uiso 1 1 calc R . . . . H10B H 0.9384 1.1155 0.5080 0.043 Uiso 1 1 calc R . . . . C11 C 0.8135(2) 1.1279(2) 0.58426(14) 0.0490(7) Uani 1 1 d . . . . . H11A H 0.7258 1.1304 0.5827 0.074 Uiso 1 1 calc GR . . . . H11B H 0.8472 1.1954 0.6061 0.074 Uiso 1 1 calc GR . . . . H11C H 0.8435 1.0658 0.6145 0.074 Uiso 1 1 calc GR . . . . C12 C 0.70368(16) 0.83082(13) 0.44956(10) 0.0175(4) Uani 1 1 d . . . . . C13 C 0.53101(18) 0.84774(15) 0.51606(11) 0.0244(4) Uani 1 1 d . . . . . H13A H 0.4686 0.9033 0.5221 0.029 Uiso 1 1 calc R . . . . H13B H 0.5879 0.8489 0.5612 0.029 Uiso 1 1 calc R . . . . C14 C 0.47293(19) 0.73670(17) 0.50822(13) 0.0322(5) Uani 1 1 d . . . . . H14A H 0.4189 0.7344 0.4625 0.048 Uiso 1 1 calc GR . . . . H14B H 0.4272 0.7228 0.5511 0.048 Uiso 1 1 calc GR . . . . H14C H 0.5351 0.6810 0.5060 0.048 Uiso 1 1 calc GR . . . . C15 C 0.61595(16) 0.69567(14) 0.27362(10) 0.0187(4) Uani 1 1 d . . . . . H15 H 0.6268 0.6313 0.2410 0.022 Uiso 1 1 calc R . . . . C16 C 0.72232(16) 0.77230(13) 0.26974(10) 0.0179(4) Uani 1 1 d . . . . . H16 H 0.7372 0.7838 0.2165 0.022 Uiso 1 1 calc R . . . . C17 C 0.70406(16) 0.88445(13) 0.30683(10) 0.0174(4) Uani 1 1 d . . . . . H17 H 0.7487 0.9390 0.2788 0.021 Uiso 1 1 calc R . . . . C18 C 0.57457(17) 0.91709(14) 0.29755(10) 0.0195(4) Uani 1 1 d . . . . . C19 C 0.48510(17) 0.85156(14) 0.26778(10) 0.0209(4) Uani 1 1 d . . . . . H19 H 0.4070 0.8814 0.2582 0.025 Uiso 1 1 calc R . . . . C20 C 0.40563(17) 0.67582(15) 0.21612(11) 0.0233(4) Uani 1 1 d . . . . . H20A H 0.4317 0.6449 0.1696 0.028 Uiso 1 1 calc R . . . . H20B H 0.3334 0.7206 0.2030 0.028 Uiso 1 1 calc R . . . . C21 C 0.37353(17) 0.58347(15) 0.26675(10) 0.0224(4) Uani 1 1 d . . . . . C22 C 0.29588(18) 0.60236(18) 0.32118(12) 0.0307(5) Uani 1 1 d . . . . . H22 H 0.2616 0.6725 0.3258 0.037 Uiso 1 1 calc R . . . . C23 C 0.2682(2) 0.5194(2) 0.36888(12) 0.0382(6) Uani 1 1 d . . . . . H23 H 0.2153 0.5332 0.4062 0.046 Uiso 1 1 calc R . . . . C24 C 0.3170(2) 0.41639(19) 0.36252(12) 0.0371(5) Uani 1 1 d . . . . . H24 H 0.2976 0.3597 0.3952 0.045 Uiso 1 1 calc R . . . . C25 C 0.39396(19) 0.39681(18) 0.30838(13) 0.0345(5) Uani 1 1 d . . . . . H25 H 0.4275 0.3264 0.3037 0.041 Uiso 1 1 calc R . . . . C26 C 0.42273(18) 0.48043(16) 0.26035(11) 0.0262(4) Uani 1 1 d . . . . . H26 H 0.4760 0.4667 0.2233 0.031 Uiso 1 1 calc R . . . . N1 N 0.87401(14) 0.80536(12) 0.37064(9) 0.0191(3) Uani 1 1 d . . . . . H1A H 0.9010(18) 0.7755(17) 0.4103(12) 0.023(6) Uiso 1 1 d . . . . . N2 N 0.50220(14) 0.74611(12) 0.25121(9) 0.0210(3) Uani 1 1 d . . . . . N3 N 0.54510(15) 1.02622(12) 0.31385(9) 0.0240(4) Uani 1 1 d . . . . . O1 O 0.60936(11) 0.65823(9) 0.34974(7) 0.0188(3) Uani 1 1 d . . . . . O2 O 0.89170(12) 1.03891(10) 0.37391(8) 0.0277(3) Uani 1 1 d . . . . . O3 O 0.80092(12) 1.01290(10) 0.47845(7) 0.0242(3) Uani 1 1 d . . . . . O4 O 0.74893(12) 0.76693(10) 0.49478(7) 0.0222(3) Uani 1 1 d . . . . . O5 O 0.59505(11) 0.87502(10) 0.45129(7) 0.0194(3) Uani 1 1 d . . . . . O6 O 0.62865(13) 1.08638(10) 0.34019(7) 0.0275(3) Uani 1 1 d . . . . . O7 O 0.44051(14) 1.06012(12) 0.30183(9) 0.0371(4) Uani 1 1 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 0.02281(10) 0.01942(9) 0.02454(11) 0.00253(7) 0.00152(7) 0.00308(7) C1 0.0184(9) 0.0191(9) 0.0166(9) -0.0033(7) 0.0038(7) -0.0019(7) C2 0.0219(10) 0.0169(8) 0.0180(9) -0.0030(7) -0.0008(8) 0.0023(7) C3 0.0260(10) 0.0158(8) 0.0231(10) 0.0025(7) 0.0031(8) -0.0016(7) C4 0.0186(10) 0.0202(9) 0.0247(10) 0.0013(7) 0.0038(8) -0.0038(7) C5 0.0187(9) 0.0162(8) 0.0167(9) -0.0038(7) 0.0002(7) 0.0009(7) C6 0.0215(10) 0.0155(8) 0.0132(9) -0.0032(7) 0.0016(7) -0.0025(7) C7 0.0198(9) 0.0169(8) 0.0159(9) -0.0001(7) 0.0055(7) -0.0021(7) C8 0.0187(9) 0.0143(8) 0.0175(9) -0.0007(7) 0.0027(7) -0.0025(7) C9 0.0225(10) 0.0161(9) 0.0207(10) 0.0011(7) 0.0012(8) 0.0001(7) C10 0.0421(14) 0.0227(10) 0.0429(14) -0.0144(9) -0.0019(11) -0.0060(9) C11 0.0486(15) 0.0554(16) 0.0415(15) -0.0269(12) -0.0056(12) 0.0074(12) C12 0.0205(10) 0.0148(8) 0.0171(9) -0.0006(7) 0.0007(8) -0.0027(7) C13 0.0254(10) 0.0274(10) 0.0221(10) 0.0029(8) 0.0109(8) -0.0009(8) C14 0.0264(11) 0.0326(11) 0.0385(13) 0.0075(9) 0.0080(10) -0.0063(9) C15 0.0221(10) 0.0181(8) 0.0158(9) -0.0001(7) 0.0012(8) 0.0010(7) C16 0.0234(10) 0.0162(8) 0.0148(9) 0.0006(7) 0.0046(7) 0.0000(7) C17 0.0241(10) 0.0149(8) 0.0135(9) 0.0015(7) 0.0029(7) -0.0004(7) C18 0.0277(10) 0.0177(9) 0.0129(9) 0.0023(7) 0.0018(8) 0.0035(7) C19 0.0244(10) 0.0225(9) 0.0158(9) 0.0045(7) 0.0016(8) 0.0043(8) C20 0.0218(10) 0.0248(10) 0.0220(10) 0.0006(8) -0.0055(8) -0.0017(7) C21 0.0190(10) 0.0283(10) 0.0192(10) -0.0013(8) -0.0027(8) -0.0060(8) C22 0.0258(11) 0.0361(11) 0.0304(11) -0.0079(9) 0.0040(9) -0.0063(9) C23 0.0317(12) 0.0579(15) 0.0259(12) -0.0042(10) 0.0078(10) -0.0182(11) C24 0.0319(12) 0.0484(14) 0.0299(12) 0.0118(10) -0.0033(10) -0.0174(10) C25 0.0311(12) 0.0300(11) 0.0412(13) 0.0077(9) -0.0030(10) -0.0063(9) C26 0.0233(11) 0.0290(10) 0.0263(11) -0.0010(8) 0.0029(9) -0.0036(8) N1 0.0197(8) 0.0176(7) 0.0198(9) -0.0016(7) 0.0013(7) -0.0006(6) N2 0.0221(8) 0.0191(7) 0.0211(8) 0.0002(6) -0.0021(7) -0.0003(6) N3 0.0351(10) 0.0203(8) 0.0165(8) 0.0017(6) 0.0021(7) 0.0057(7) O1 0.0189(7) 0.0191(6) 0.0188(7) 0.0024(5) 0.0030(5) 0.0005(5) O2 0.0339(8) 0.0216(7) 0.0291(8) 0.0011(6) 0.0101(6) -0.0097(6) O3 0.0347(8) 0.0191(6) 0.0190(7) -0.0042(5) 0.0040(6) -0.0056(6) O4 0.0245(7) 0.0213(6) 0.0209(7) 0.0064(5) 0.0030(6) 0.0006(5) O5 0.0207(7) 0.0211(6) 0.0172(6) 0.0035(5) 0.0059(5) 0.0008(5) O6 0.0372(8) 0.0178(6) 0.0267(8) -0.0022(6) -0.0008(6) -0.0005(6) O7 0.0352(9) 0.0332(8) 0.0411(9) -0.0067(7) -0.0061(7) 0.0168(7) 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' N N 0.0061 0.0033 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1 120.3 . . ? C2 C1 C6 119.31(17) . . ? C6 C1 H1 120.3 . . ? C1 C2 Br1 119.52(14) . . ? C3 C2 Br1 118.99(13) . . ? C3 C2 C1 121.46(17) . . ? C2 C3 H3 120.2 . . ? C2 C3 C4 119.54(17) . . ? C4 C3 H3 120.2 . . ? C3 C4 H4 120.6 . . ? C5 C4 C3 118.87(17) . . ? C5 C4 H4 120.6 . . ? C4 C5 C6 121.99(16) . . ? O1 C5 C4 118.97(16) . . ? O1 C5 C6 119.04(15) . . ? C1 C6 C7 121.88(16) . . ? C5 C6 C1 118.79(16) . . ? C5 C6 C7 118.88(15) . . ? C6 C7 H7 109.2 . . ? C6 C7 C16 113.78(14) . . ? C16 C7 H7 109.2 . . ? N1 C7 C6 110.53(14) . . ? N1 C7 H7 109.2 . . ? N1 C7 C16 104.88(14) . . ? C9 C8 C17 110.63(14) . . ? C12 C8 C9 107.82(14) . . ? C12 C8 C17 118.26(15) . . ? N1 C8 C9 105.66(14) . . ? N1 C8 C12 112.11(14) . . ? N1 C8 C17 101.63(14) . . ? O2 C9 C8 123.80(17) . . ? O2 C9 O3 124.58(17) . . ? O3 C9 C8 111.54(14) . . ? H10A C10 H10B 108.5 . . ? C11 C10 H10A 110.3 . . ? C11 C10 H10B 110.3 . . ? O3 C10 H10A 110.3 . . ? O3 C10 H10B 110.3 . . ? O3 C10 C11 107.24(18) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O4 C12 C8 121.87(16) . . ? O4 C12 O5 125.13(16) . . ? O5 C12 C8 112.89(14) . . ? H13A C13 H13B 108.0 . . ? C14 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? O5 C13 H13A 109.3 . . ? O5 C13 H13B 109.3 . . ? O5 C13 C14 111.62(16) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 H15 109.0 . . ? N2 C15 H15 109.0 . . ? N2 C15 C16 113.30(15) . . ? N2 C15 O1 106.46(14) . . ? O1 C15 H15 109.0 . . ? O1 C15 C16 110.08(14) . . ? C7 C16 H16 109.2 . . ? C15 C16 C7 110.67(14) . . ? C15 C16 H16 109.2 . . ? C15 C16 C17 113.25(15) . . ? C17 C16 C7 105.17(14) . . ? C17 C16 H16 109.2 . . ? C8 C17 H17 106.6 . . ? C16 C17 C8 104.82(14) . . ? C16 C17 H17 106.6 . . ? C18 C17 C8 120.88(15) . . ? C18 C17 C16 110.61(15) . . ? C18 C17 H17 106.6 . . ? C19 C18 C17 123.87(16) . . ? C19 C18 N3 117.77(17) . . ? N3 C18 C17 118.05(16) . . ? C18 C19 H19 118.5 . . ? N2 C19 C18 122.95(17) . . ? N2 C19 H19 118.5 . . ? H20A C20 H20B 107.9 . . ? C21 C20 H20A 109.1 . . ? C21 C20 H20B 109.1 . . ? N2 C20 H20A 109.1 . . ? N2 C20 H20B 109.1 . . ? N2 C20 C21 112.35(15) . . ? C22 C21 C20 119.83(18) . . ? C22 C21 C26 119.26(18) . . ? C26 C21 C20 120.90(17) . . ? C21 C22 H22 119.8 . . ? C23 C22 C21 120.4(2) . . ? C23 C22 H22 119.8 . . ? C22 C23 H23 119.8 . . ? C24 C23 C22 120.5(2) . . ? C24 C23 H23 119.8 . . ? C23 C24 H24 120.2 . . ? C25 C24 C23 119.5(2) . . ? C25 C24 H24 120.2 . . ? C24 C25 H25 119.9 . . ? C24 C25 C26 120.2(2) . . ? C26 C25 H25 119.9 . . ? C21 C26 C25 120.15(19) . . ? C21 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C7 N1 H1A 111.5(14) . . ? C8 N1 C7 110.58(14) . . ? C8 N1 H1A 109.0(14) . . ? C15 N2 C20 117.53(14) . . ? C19 N2 C15 119.37(15) . . ? C19 N2 C20 122.90(16) . . ? O6 N3 C18 117.22(16) . . ? O7 N3 C18 120.88(16) . . ? O7 N3 O6 121.90(16) . . ? C5 O1 C15 109.52(13) . . ? C9 O3 C10 115.84(15) . . ? C12 O5 C13 115.92(14) . . ? 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 C2 1.9088(19) . ? C1 H1 0.9500 . ? C1 C2 1.390(2) . ? C1 C6 1.394(3) . ? C2 C3 1.387(3) . ? C3 H3 0.9500 . ? C3 C4 1.393(3) . ? C4 H4 0.9500 . ? C4 C5 1.385(2) . ? C5 C6 1.394(3) . ? C5 O1 1.384(2) . ? C6 C7 1.524(2) . ? C7 H7 1.0000 . ? C7 C16 1.556(3) . ? C7 N1 1.487(2) . ? C8 C9 1.550(2) . ? C8 C12 1.544(2) . ? C8 C17 1.557(3) . ? C8 N1 1.469(2) . ? C9 O2 1.204(2) . ? C9 O3 1.331(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C11 1.489(3) . ? C10 O3 1.456(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O4 1.211(2) . ? C12 O5 1.335(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.513(3) . ? C13 O5 1.464(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15 1.0000 . ? C15 C16 1.524(2) . ? C15 N2 1.441(2) . ? C15 O1 1.458(2) . ? C16 H16 1.0000 . ? C16 C17 1.554(2) . ? C17 H17 1.0000 . ? C17 C18 1.499(3) . ? C18 C19 1.358(3) . ? C18 N3 1.418(2) . ? C19 H19 0.9500 . ? C19 N2 1.347(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 C21 1.520(3) . ? C20 N2 1.481(2) . ? C21 C22 1.388(3) . ? C21 C26 1.390(3) . ? C22 H22 0.9500 . ? C22 C23 1.388(3) . ? C23 H23 0.9500 . ? C23 C24 1.387(3) . ? C24 H24 0.9500 . ? C24 C25 1.381(3) . ? C25 H25 0.9500 . ? C25 C26 1.401(3) . ? C26 H26 0.9500 . ? N1 H1A 0.84(2) . ? N3 O6 1.252(2) . ? N3 O7 1.244(2) . ? 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 Br1 C2 C3 C4 178.81(14) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C1 C6 C7 C16 158.88(16) . . . . ? C1 C6 C7 N1 -83.4(2) . . . . ? C2 C1 C6 C5 -2.2(3) . . . . ? C2 C1 C6 C7 169.95(16) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C3 C4 C5 O1 -178.97(16) . . . . ? C4 C5 C6 C1 1.6(3) . . . . ? C4 C5 C6 C7 -170.78(16) . . . . ? C4 C5 O1 C15 -139.72(16) . . . . ? C5 C6 C7 C16 -29.0(2) . . . . ? C5 C6 C7 N1 88.73(19) . . . . ? C6 C1 C2 Br1 -176.94(13) . . . . ? C6 C1 C2 C3 1.0(3) . . . . ? C6 C5 O1 C15 41.1(2) . . . . ? C6 C7 C16 C15 0.0(2) . . . . ? C6 C7 C16 C17 122.68(15) . . . . ? C6 C7 N1 C8 -101.64(17) . . . . ? C7 C16 C17 C8 -22.31(17) . . . . ? C7 C16 C17 C18 -154.12(14) . . . . ? C8 C9 O3 C10 179.48(16) . . . . ? C8 C12 O5 C13 -172.29(14) . . . . ? C8 C17 C18 C19 -116.38(19) . . . . ? C8 C17 C18 N3 70.2(2) . . . . ? C9 C8 C12 O4 -95.70(19) . . . . ? C9 C8 C12 O5 80.72(18) . . . . ? C9 C8 C17 C16 146.17(14) . . . . ? C9 C8 C17 C18 -88.21(19) . . . . ? C9 C8 N1 C7 -150.58(14) . . . . ? C11 C10 O3 C9 -177.89(18) . . . . ? C12 C8 C9 O2 176.37(18) . . . . ? C12 C8 C9 O3 -0.6(2) . . . . ? C12 C8 C17 C16 -88.83(17) . . . . ? C12 C8 C17 C18 36.8(2) . . . . ? C12 C8 N1 C7 92.23(17) . . . . ? C14 C13 O5 C12 -80.0(2) . . . . ? C15 C16 C17 C8 98.66(17) . . . . ? C15 C16 C17 C18 -33.1(2) . . . . ? C16 C7 N1 C8 21.38(18) . . . . ? C16 C15 N2 C19 -35.6(2) . . . . ? C16 C15 N2 C20 149.38(16) . . . . ? C16 C15 O1 C5 -70.11(17) . . . . ? C16 C17 C18 C19 6.5(2) . . . . ? C16 C17 C18 N3 -166.93(15) . . . . ? C17 C8 C9 O2 -52.9(2) . . . . ? C17 C8 C9 O3 130.17(16) . . . . ? C17 C8 C12 O4 137.93(17) . . . . ? C17 C8 C12 O5 -45.7(2) . . . . ? C17 C8 N1 C7 -35.02(17) . . . . ? C17 C18 C19 N2 7.6(3) . . . . ? C17 C18 N3 O6 -5.1(2) . . . . ? C17 C18 N3 O7 174.50(16) . . . . ? C18 C19 N2 C15 7.6(3) . . . . ? C18 C19 N2 C20 -177.62(17) . . . . ? C19 C18 N3 O6 -178.91(16) . . . . ? C19 C18 N3 O7 0.6(3) . . . . ? C20 C21 C22 C23 -178.46(18) . . . . ? C20 C21 C26 C25 178.77(18) . . . . ? C21 C20 N2 C15 59.5(2) . . . . ? C21 C20 N2 C19 -115.29(19) . . . . ? C21 C22 C23 C24 -0.4(3) . . . . ? C22 C21 C26 C25 0.0(3) . . . . ? C22 C23 C24 C25 0.2(3) . . . . ? C23 C24 C25 C26 0.2(3) . . . . ? C24 C25 C26 C21 -0.3(3) . . . . ? C26 C21 C22 C23 0.3(3) . . . . ? N1 C7 C16 C15 -120.87(15) . . . . ? N1 C7 C16 C17 1.78(17) . . . . ? N1 C8 C9 O2 56.3(2) . . . . ? N1 C8 C9 O3 -120.60(16) . . . . ? N1 C8 C12 O4 20.2(2) . . . . ? N1 C8 C12 O5 -163.40(14) . . . . ? N1 C8 C17 C16 34.34(16) . . . . ? N1 C8 C17 C18 159.96(15) . . . . ? N2 C15 C16 C7 165.95(14) . . . . ? N2 C15 C16 C17 48.1(2) . . . . ? N2 C15 O1 C5 166.72(13) . . . . ? N2 C20 C21 C22 82.1(2) . . . . ? N2 C20 C21 C26 -96.7(2) . . . . ? N3 C18 C19 N2 -178.89(16) . . . . ? O1 C5 C6 C1 -179.19(15) . . . . ? O1 C5 C6 C7 8.4(2) . . . . ? O1 C15 C16 C7 46.88(18) . . . . ? O1 C15 C16 C17 -70.93(18) . . . . ? O1 C15 N2 C19 85.53(18) . . . . ? O1 C15 N2 C20 -89.49(17) . . . . ? O2 C9 O3 C10 2.6(3) . . . . ? O4 C12 O5 C13 4.0(2) . . . . ?