#------------------------------------------------------------------------------ #$Date: 2019-12-17 03:49:01 +0200 (Tue, 17 Dec 2019) $ #$Revision: 245228 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125661.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_7125661 loop_ _publ_author_name 'Wang, Yan-Bo' 'Yang, Wan-Wan' 'Chen, Lu-Lu' 'Chen, Pei' 'Ye, Ya-Fang' 'Zhang, Xiao' _publ_section_title ; Solvent-controlled divergent annulation of ynones and (iso)quinoline N‑oxides: synthesis of 3-((iso)quinolin-1-yl)-4H-chromen-4-ones and 13H-isoquinolino[2,1-a]quinolin-13-ones ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC08713C _journal_year 2020 _chemical_formula_moiety 'C25 H18 Br N O2' _chemical_formula_sum 'C25 H18 Br N O2' _chemical_formula_weight 444.31 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-10-16 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-10-16 deposited with the CCDC. 2019-12-16 downloaded from the CCDC. ; _cell_angle_alpha 77.759(8) _cell_angle_beta 88.648(9) _cell_angle_gamma 85.507(8) _cell_formula_units_Z 4 _cell_length_a 7.411(2) _cell_length_b 12.752(4) _cell_length_c 21.926(6) _cell_measurement_reflns_used 3771 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 22.80 _cell_measurement_theta_min 2.23 _cell_volume 2018.7(10) _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 298.0 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0827 _diffrn_reflns_av_unetI/netI 0.1051 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 31422 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.331 _diffrn_reflns_theta_min 2.233 _exptl_absorpt_coefficient_mu 2.057 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0955 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.8137. The \l/2 correction factor is Not present.' _exptl_crystal_colour green _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 1.462 _exptl_crystal_description block _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _refine_diff_density_max 1.036 _refine_diff_density_min -0.996 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 525 _refine_ls_number_reflns 9993 _refine_ls_number_restraints 39 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.1752 _refine_ls_R_factor_gt 0.0627 _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^)+(0.0801P)^2^+0.1978P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1480 _refine_ls_wR_factor_ref 0.1901 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4350 _reflns_number_total 9993 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; a.res created by SHELXL-2014/7 TITL A in P-1 #2 REM reset to P-1 #2 CELL 0.71073 7.4114 12.7519 21.9258 77.759 88.648 85.507 ZERR 4 0.0021 0.0038 0.0061 0.008 0.009 0.008 LATT 1 SFAC C H Br N O UNIT 100 72 4 4 8 DELU 0.001 0.001 C4' C5' DELU 0.001 0.001 C5' C6' DELU 0.001 0.001 C2' C1' ISOR 0.01 0.02 C5' C4' C3' C2' C1' C6' L.S. 11 0 0 PLAN 20 SIZE 0.15 0.12 0.07 TEMP 24.85 MPLA C1 C2 C3 C4 C5 C6 MPLA C10 C11 C12 C13 C14 C15 MPLA C17 C18 C19 C20 C21 C22 C23 C24 C25 N1 MPLA C1' C2' C3' C4' C5' C6' MPLA C10' C11' C12' C13' C14' C15' MPLA C17' C18' C19' C20' C21' C22' C23' C24' C25' N1' HTAB N1 O1 HTAB N1' O1' BOND $h conf fmap 2 acta REM REM REM WGHT 0.080100 0.197800 FVAR 0.09894 BR1 3 0.538992 0.429430 0.239159 11.00000 0.05748 0.07065 = 0.11864 -0.03314 -0.00982 -0.01196 C1 1 0.319099 0.361110 0.252164 11.00000 0.04812 0.04958 = 0.05152 -0.01260 -0.01114 0.00464 C2 1 0.176437 0.410997 0.279683 11.00000 0.05928 0.05260 = 0.06137 -0.02731 -0.00964 0.01280 AFIX 43 H2 2 0.191336 0.474153 0.293179 11.00000 -1.20000 AFIX 0 C3 1 0.013848 0.366621 0.286806 11.00000 0.05332 0.07419 = 0.05727 -0.02585 -0.00337 0.01441 AFIX 43 H3 2 -0.083371 0.400854 0.304269 11.00000 -1.20000 AFIX 0 C4 1 -0.008052 0.271744 0.268450 11.00000 0.05139 0.07354 = 0.04615 -0.00354 0.00261 -0.01121 AFIX 43 H4 2 -0.120166 0.242852 0.273725 11.00000 -1.20000 AFIX 0 C5 1 0.131992 0.218935 0.242545 11.00000 0.05275 0.04679 = 0.03599 -0.01171 -0.00771 0.00817 AFIX 43 H5 2 0.117112 0.153406 0.231810 11.00000 -1.20000 AFIX 0 C6 1 0.300684 0.266355 0.232394 11.00000 0.04543 0.04356 = 0.03850 -0.01100 -0.00646 0.00706 C7 1 0.457045 0.210614 0.203155 11.00000 0.04494 0.03535 = 0.05100 -0.01033 -0.00190 0.00429 C8 1 0.439093 0.201098 0.140038 11.00000 0.04309 0.03599 = 0.04252 -0.01019 -0.00050 0.00400 C9 1 0.259447 0.238434 0.110107 11.00000 0.04634 0.04095 = 0.03899 -0.00912 0.00076 0.00161 C10 1 0.199946 0.355810 0.097591 11.00000 0.04323 0.04141 = 0.04054 -0.01034 -0.00570 0.00470 C11 1 0.324568 0.432658 0.085367 11.00000 0.04839 0.04709 = 0.05841 -0.00965 -0.00677 0.00266 AFIX 43 H11 2 0.447579 0.411439 0.087974 11.00000 -1.20000 AFIX 0 C12 1 0.268370 0.541170 0.069239 11.00000 0.07176 0.04108 = 0.06493 -0.00840 -0.01144 -0.00595 AFIX 43 H12 2 0.354868 0.591365 0.059998 11.00000 -1.20000 AFIX 0 C13 1 0.086334 0.576809 0.066529 11.00000 0.07084 0.04501 = 0.04581 -0.01584 -0.01657 0.01100 C14 1 -0.036094 0.499088 0.080344 11.00000 0.05071 0.06216 = 0.06250 -0.02415 -0.01837 0.02024 AFIX 43 H14 2 -0.159009 0.520569 0.079624 11.00000 -1.20000 AFIX 0 C15 1 0.017063 0.389900 0.095304 11.00000 0.04847 0.05100 = 0.05555 -0.01873 -0.00539 -0.00183 AFIX 43 H15 2 -0.069563 0.339695 0.103774 11.00000 -1.20000 AFIX 0 C16 1 0.028662 0.694324 0.047772 11.00000 0.10747 0.05042 = 0.06804 -0.01636 -0.02472 0.02037 AFIX 137 H16A 2 0.050430 0.718871 0.003916 11.00000 -1.50000 H16B 2 0.096628 0.733754 0.070828 11.00000 -1.50000 H16C 2 -0.098030 0.705654 0.056551 11.00000 -1.50000 AFIX 0 C17 1 0.572348 0.140896 0.111718 11.00000 0.04466 0.03772 = 0.04853 -0.01130 0.00206 -0.00216 C18 1 0.828877 0.009993 0.128430 11.00000 0.04164 0.04874 = 0.08516 -0.01769 0.00230 0.01009 AFIX 43 H18 2 0.916724 -0.027401 0.156023 11.00000 -1.20000 AFIX 0 C19 1 0.824890 -0.006312 0.070409 11.00000 0.04791 0.05121 = 0.08110 -0.03119 0.01857 0.00071 AFIX 43 H19 2 0.901478 -0.060306 0.058944 11.00000 -1.20000 AFIX 0 C20 1 0.705243 0.057892 0.026539 11.00000 0.04611 0.04897 = 0.06286 -0.02335 0.01706 -0.01396 C21 1 0.582428 0.135979 0.045500 11.00000 0.04130 0.04607 = 0.04905 -0.01520 0.00856 -0.00838 C22 1 0.478702 0.208285 -0.000505 11.00000 0.05620 0.05360 = 0.04518 -0.01294 0.01000 -0.00564 AFIX 43 H22 2 0.403400 0.262880 0.010892 11.00000 -1.20000 AFIX 0 C23 1 0.487169 0.199309 -0.062210 11.00000 0.06900 0.06939 = 0.05223 -0.00592 0.00188 -0.01212 AFIX 43 H23 2 0.418924 0.247733 -0.092234 11.00000 -1.20000 AFIX 0 C24 1 0.599188 0.116832 -0.078948 11.00000 0.07875 0.08751 = 0.05066 -0.02920 0.02299 -0.02913 AFIX 43 H24 2 0.601078 0.108804 -0.120143 11.00000 -1.20000 AFIX 0 C25 1 0.705422 0.048081 -0.036445 11.00000 0.05747 0.06250 = 0.07339 -0.03445 0.02517 -0.01837 AFIX 43 H25 2 0.779220 -0.006129 -0.048874 11.00000 -1.20000 AFIX 0 N1 4 0.705072 0.081050 0.147435 11.00000 0.04773 0.05130 = 0.04938 -0.01273 -0.00150 0.00965 AFIX 43 H1 2 0.711727 0.088570 0.185361 11.00000 -1.20000 AFIX 0 O1 5 0.587084 0.169746 0.238073 11.00000 0.05512 0.06728 = 0.05722 -0.01976 -0.01820 0.02375 O2 5 0.163947 0.175713 0.094335 11.00000 0.05487 0.04736 = 0.06094 -0.01808 -0.00835 -0.00511 BR1' 3 -0.291385 0.109501 0.738117 11.00000 0.07705 0.13107 = 0.09075 -0.02585 0.02583 0.01280 C1' 1 -0.104331 0.195000 0.748516 11.00000 0.10348 0.05836 = 0.04792 -0.00953 0.00502 0.02128 C2' 1 -0.145002 0.278438 0.782278 11.00000 0.15699 0.07910 = 0.05382 -0.01998 0.01730 0.03343 AFIX 43 H2' 2 -0.260331 0.290944 0.798127 11.00000 -1.20000 AFIX 0 C3' 1 -0.007843 0.338408 0.790111 11.00000 0.19053 0.06003 = 0.07301 -0.02404 -0.00711 0.01125 AFIX 43 H3' 2 -0.032966 0.394151 0.811071 11.00000 -1.20000 AFIX 0 C4' 1 0.166291 0.322153 0.769049 11.00000 0.17311 0.07231 = 0.07648 -0.02924 -0.02617 -0.02320 AFIX 43 H4' 2 0.254718 0.364270 0.778175 11.00000 -1.20000 AFIX 0 C5' 1 0.212543 0.245904 0.735147 11.00000 0.14275 0.05190 = 0.05575 -0.00348 -0.02083 -0.00628 AFIX 43 H5' 2 0.329359 0.236064 0.719852 11.00000 -1.20000 AFIX 0 C6' 1 0.066790 0.179873 0.724094 11.00000 0.09552 0.04757 = 0.03767 -0.00873 -0.00669 0.01892 C7' 1 0.115365 0.089754 0.690626 11.00000 0.04388 0.03892 = 0.04981 -0.01340 -0.00262 0.00438 C8' 1 0.166557 0.113950 0.627607 11.00000 0.04171 0.02920 = 0.04795 -0.01071 0.00023 0.00419 C9' 1 0.198830 0.226590 0.595859 11.00000 0.04746 0.03960 = 0.04120 -0.01360 -0.00286 -0.00169 C10' 1 0.051343 0.314186 0.592815 11.00000 0.04875 0.03912 = 0.03807 -0.01274 0.00036 -0.00196 C11' 1 -0.128310 0.294028 0.593267 11.00000 0.05393 0.03606 = 0.06000 -0.01082 0.00089 -0.00419 AFIX 43 H11' 2 -0.159143 0.223362 0.598413 11.00000 -1.20000 AFIX 0 C12' 1 -0.264298 0.376328 0.586250 11.00000 0.04586 0.05289 = 0.06123 -0.00997 -0.00633 0.00496 AFIX 43 H12' 2 -0.384702 0.360449 0.586520 11.00000 -1.20000 AFIX 0 C13' 1 -0.222136 0.482284 0.578823 11.00000 0.07455 0.04533 = 0.04479 -0.01205 -0.00188 0.01737 C14' 1 -0.042501 0.501975 0.578358 11.00000 0.07588 0.03475 = 0.05690 -0.01477 -0.00209 0.00323 AFIX 43 H14' 2 -0.012139 0.572676 0.573540 11.00000 -1.20000 AFIX 0 C15' 1 0.093890 0.421251 0.584733 11.00000 0.05566 0.03794 = 0.05588 -0.01092 0.00037 -0.00440 AFIX 43 H15' 2 0.214145 0.437665 0.583685 11.00000 -1.20000 AFIX 0 C16' 1 -0.368691 0.572373 0.570352 11.00000 0.08501 0.05714 = 0.07621 -0.00916 -0.00778 0.02385 AFIX 137 H16D 2 -0.394343 0.596978 0.526724 11.00000 -1.50000 H16E 2 -0.329290 0.630657 0.586854 11.00000 -1.50000 H16F 2 -0.476077 0.547044 0.592066 11.00000 -1.50000 AFIX 0 C17' 1 0.225785 0.029795 0.595495 11.00000 0.03171 0.03416 = 0.04782 -0.00605 0.00283 -0.00015 C18' 1 0.350303 -0.154244 0.607922 11.00000 0.05402 0.03317 = 0.06784 -0.01000 0.00677 0.00522 AFIX 43 H18' 2 0.385553 -0.218555 0.635230 11.00000 -1.20000 AFIX 0 C19' 1 0.367101 -0.147448 0.546993 11.00000 0.04951 0.04018 = 0.06633 -0.02063 0.00582 0.00083 AFIX 43 H19' 2 0.420637 -0.205241 0.531737 11.00000 -1.20000 AFIX 0 C20' 1 0.302968 -0.051383 0.504842 11.00000 0.03400 0.04282 = 0.05752 -0.02225 0.00535 -0.00672 C21' 1 0.226385 0.036550 0.529321 11.00000 0.03648 0.03687 = 0.04392 -0.01444 0.00529 -0.00603 C22' 1 0.145173 0.126217 0.487712 11.00000 0.03999 0.04421 = 0.05474 -0.01356 0.00145 0.00319 AFIX 43 H22' 2 0.089557 0.183251 0.503180 11.00000 -1.20000 AFIX 0 C23' 1 0.146835 0.130769 0.424365 11.00000 0.05178 0.05697 = 0.05140 -0.01060 -0.00407 -0.00059 AFIX 43 H23' 2 0.091500 0.190224 0.397416 11.00000 -1.20000 AFIX 0 C24' 1 0.231695 0.046014 0.400658 11.00000 0.06107 0.07141 = 0.04516 -0.02043 -0.00426 -0.00925 AFIX 43 H24' 2 0.236867 0.050464 0.357771 11.00000 -1.20000 AFIX 0 C25' 1 0.306199 -0.042269 0.439629 11.00000 0.04948 0.05688 = 0.05500 -0.02788 0.00500 -0.00628 AFIX 43 H25' 2 0.360911 -0.098367 0.423107 11.00000 -1.20000 AFIX 0 N1' 4 0.281465 -0.067503 0.631316 11.00000 0.05530 0.03766 = 0.04684 -0.00943 0.00690 0.00160 AFIX 43 H1' 2 0.273045 -0.075238 0.671185 11.00000 -1.20000 AFIX 0 O1' 5 0.115123 -0.003583 0.724003 11.00000 0.07112 0.04096 = 0.04954 -0.00375 0.01073 0.00512 O2' 5 0.344680 0.247449 0.570989 11.00000 0.04712 0.04406 = 0.07387 -0.01101 0.01330 -0.00487 HKLF 4 REM A in P-1 #2 REM R1 = 0.0627 for 4350 Fo > 4sig(Fo) and 0.1752 for all 9993 data REM 525 parameters refined using 39 restraints END WGHT 0.0800 0.2148 REM Highest difference peak 1.036, deepest hole -0.996, 1-sigma level 0.067 Q1 1 0.3313 0.2625 0.7399 11.00000 0.05 1.04 Q2 1 0.1411 0.2349 0.7376 11.00000 0.05 0.35 Q3 1 -0.2720 0.1937 0.7433 11.00000 0.05 0.35 Q4 1 -0.1296 0.3465 0.7885 11.00000 0.05 0.31 Q5 1 0.6036 0.4426 0.1969 11.00000 0.05 0.28 Q6 1 0.0965 0.3561 0.7802 11.00000 0.05 0.28 Q7 1 0.0632 0.1998 0.7030 11.00000 0.05 0.25 Q8 1 0.1753 0.2391 0.2450 11.00000 0.05 0.25 Q9 1 0.1204 0.2245 0.2676 11.00000 0.05 0.25 Q10 1 -0.5075 0.0390 0.7621 11.00000 0.05 0.24 Q11 1 -0.0566 0.2722 0.2600 11.00000 0.05 0.22 Q12 1 -0.0495 0.7241 0.1175 11.00000 0.05 0.22 Q13 1 0.6720 0.1203 0.0321 11.00000 0.05 0.22 Q14 1 0.6087 0.1438 0.0710 11.00000 0.05 0.22 Q15 1 -0.3216 0.2586 0.7797 11.00000 0.05 0.21 Q16 1 -0.2467 0.2482 0.7595 11.00000 0.05 0.21 Q17 1 -0.2858 0.2570 0.7664 11.00000 0.05 0.21 Q18 1 0.2909 -0.0033 0.5066 11.00000 0.05 0.21 Q19 1 0.1101 0.1520 0.7276 11.00000 0.05 0.21 Q20 1 0.1408 0.1687 0.2541 11.00000 0.05 0.21 REM The information below was added by Olex2. REM REM R1 = 0.0627 for 4350 Fo > 4sig(Fo) and 0.1752 for all 31422 data REM n/a parameters refined using n/a restraints REM Highest difference peak 1.04, deepest hole -1.00 REM Mean Shift 0, Max Shift -0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1752 REM R1_gt = 0.0627 REM wR_ref = 0.1901 REM GOOF = 1.022 REM Shift_max = -0.001 REM Shift_mean = 0 REM Reflections_all = 31422 REM Reflections_gt = 4350 REM Parameters = n/a REM Hole = -1.00 REM Peak = 1.04 REM Flack = n/a ; _cod_data_source_file c9cc08713c2.cif _cod_data_source_block a _cod_original_cell_volume 2018.8(10) _cod_database_code 7125661 _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 0.869 _shelx_estimated_absorpt_t_min 0.748 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Rigid bond restraints C4', C5' with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 C5', C6' with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 C2', C1' with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 3. Uiso/Uaniso restraints and constraints Uanis(C5') \\sim Ueq, Uanis(C4') \\sim Ueq, Uanis(C3') \\sim Ueq, Uanis(C2') \\sim Ueq, Uanis(C1') \\sim Ueq, Uanis(C6') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 4.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), N1(H1), C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C11'(H11'), C12'(H12'), C14'(H14'), C15'(H15'), C18'(H18'), C19'(H19'), C22'(H22'), C23'(H23'), C24'(H24'), C25'(H25'), N1'(H1') 4.b Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C16'(H16D,H16E,H16F) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-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 Br1 Br 0.53899(7) 0.42943(5) 0.23916(3) 0.0798(2) Uani 1 1 d . . C1 C 0.3191(6) 0.3611(4) 0.2522(2) 0.0497(11) Uani 1 1 d . . C2 C 0.1764(7) 0.4110(4) 0.2797(2) 0.0562(12) Uani 1 1 d . . H2 H 0.1913 0.4742 0.2932 0.067 Uiso 1 1 calc R . C3 C 0.0138(7) 0.3666(4) 0.2868(2) 0.0608(13) Uani 1 1 d . . H3 H -0.0834 0.4009 0.3043 0.073 Uiso 1 1 calc R . C4 C -0.0081(6) 0.2717(4) 0.2684(2) 0.0581(12) Uani 1 1 d . . H4 H -0.1202 0.2429 0.2737 0.070 Uiso 1 1 calc R . C5 C 0.1320(6) 0.2189(4) 0.24255(18) 0.0453(10) Uani 1 1 d . . H5 H 0.1171 0.1534 0.2318 0.054 Uiso 1 1 calc R . C6 C 0.3007(6) 0.2664(3) 0.23239(18) 0.0426(10) Uani 1 1 d . . C7 C 0.4570(6) 0.2106(3) 0.2032(2) 0.0439(10) Uani 1 1 d . . C8 C 0.4391(5) 0.2011(3) 0.14004(18) 0.0406(10) Uani 1 1 d . . C9 C 0.2594(6) 0.2384(3) 0.11011(19) 0.0423(10) Uani 1 1 d . . C10 C 0.1999(6) 0.3558(3) 0.09759(19) 0.0418(10) Uani 1 1 d . . C11 C 0.3246(6) 0.4327(3) 0.0854(2) 0.0517(11) Uani 1 1 d . . H11 H 0.4476 0.4114 0.0880 0.062 Uiso 1 1 calc R . C12 C 0.2684(7) 0.5412(4) 0.0692(2) 0.0594(13) Uani 1 1 d . . H12 H 0.3549 0.5914 0.0600 0.071 Uiso 1 1 calc R . C13 C 0.0863(7) 0.5768(4) 0.0665(2) 0.0535(12) Uani 1 1 d . . C14 C -0.0361(7) 0.4991(4) 0.0803(2) 0.0578(13) Uani 1 1 d . . H14 H -0.1590 0.5206 0.0796 0.069 Uiso 1 1 calc R . C15 C 0.0171(6) 0.3899(4) 0.0953(2) 0.0506(11) Uani 1 1 d . . H15 H -0.0696 0.3397 0.1038 0.061 Uiso 1 1 calc R . C16 C 0.0287(8) 0.6943(4) 0.0478(2) 0.0758(16) Uani 1 1 d . . H16A H 0.0504 0.7189 0.0039 0.114 Uiso 1 1 calc GR . H16B H 0.0966 0.7338 0.0708 0.114 Uiso 1 1 calc GR . H16C H -0.0980 0.7057 0.0566 0.114 Uiso 1 1 calc GR . C17 C 0.5723(6) 0.1409(3) 0.11172(19) 0.0434(10) Uani 1 1 d . . C18 C 0.8289(6) 0.0100(4) 0.1284(3) 0.0588(13) Uani 1 1 d . . H18 H 0.9167 -0.0274 0.1560 0.071 Uiso 1 1 calc R . C19 C 0.8249(6) -0.0063(4) 0.0704(2) 0.0581(13) Uani 1 1 d . . H19 H 0.9015 -0.0603 0.0589 0.070 Uiso 1 1 calc R . C20 C 0.7052(6) 0.0579(4) 0.0265(2) 0.0507(11) Uani 1 1 d . . C21 C 0.5824(6) 0.1360(3) 0.0455(2) 0.0446(10) Uani 1 1 d . . C22 C 0.4787(6) 0.2083(4) -0.0005(2) 0.0514(11) Uani 1 1 d . . H22 H 0.4034 0.2629 0.0109 0.062 Uiso 1 1 calc R . C23 C 0.4872(7) 0.1993(4) -0.0622(2) 0.0642(13) Uani 1 1 d . . H23 H 0.4189 0.2477 -0.0922 0.077 Uiso 1 1 calc R . C24 C 0.5992(8) 0.1168(5) -0.0789(2) 0.0693(15) Uani 1 1 d . . H24 H 0.6011 0.1088 -0.1201 0.083 Uiso 1 1 calc R . C25 C 0.7054(7) 0.0481(4) -0.0364(3) 0.0611(13) Uani 1 1 d . . H25 H 0.7792 -0.0061 -0.0489 0.073 Uiso 1 1 calc R . N1 N 0.7051(5) 0.0811(3) 0.14744(17) 0.0499(9) Uani 1 1 d . . H1 H 0.7117 0.0886 0.1854 0.060 Uiso 1 1 calc R . O1 O 0.5871(4) 0.1697(3) 0.23807(15) 0.0601(9) Uani 1 1 d . . O2 O 0.1639(4) 0.1757(2) 0.09433(14) 0.0532(8) Uani 1 1 d . . Br1' Br -0.29139(9) 0.10950(6) 0.73812(3) 0.1008(3) Uani 1 1 d . . C1' C -0.1043(8) 0.1950(4) 0.7485(2) 0.0717(15) Uani 1 1 d . U C2' C -0.1450(12) 0.2784(5) 0.7823(3) 0.098(2) Uani 1 1 d . U H2' H -0.2603 0.2909 0.7981 0.118 Uiso 1 1 calc R . C3' C -0.0078(14) 0.3384(5) 0.7901(3) 0.107(2) Uani 1 1 d . U H3' H -0.0330 0.3942 0.8111 0.129 Uiso 1 1 calc R . C4' C 0.1663(13) 0.3222(5) 0.7690(3) 0.104(2) Uani 1 1 d . U H4' H 0.2547 0.3643 0.7782 0.125 Uiso 1 1 calc R . C5' C 0.2125(10) 0.2459(4) 0.7351(2) 0.0844(16) Uani 1 1 d . U H5' H 0.3294 0.2361 0.7199 0.101 Uiso 1 1 calc R . C6' C 0.0668(8) 0.1799(4) 0.7241(2) 0.0615(12) Uani 1 1 d . U C7' C 0.1154(6) 0.0898(3) 0.6906(2) 0.0440(10) Uani 1 1 d . . C8' C 0.1666(5) 0.1140(3) 0.62761(19) 0.0396(9) Uani 1 1 d . . C9' C 0.1988(6) 0.2266(3) 0.59586(19) 0.0420(10) Uani 1 1 d . . C10' C 0.0513(6) 0.3142(3) 0.59282(18) 0.0414(10) Uani 1 1 d . . C11' C -0.1283(6) 0.2940(3) 0.5933(2) 0.0499(11) Uani 1 1 d . . H11' H -0.1591 0.2234 0.5984 0.060 Uiso 1 1 calc R . C12' C -0.2643(6) 0.3763(4) 0.5863(2) 0.0540(12) Uani 1 1 d . . H12' H -0.3847 0.3604 0.5865 0.065 Uiso 1 1 calc R . C13' C -0.2221(7) 0.4823(4) 0.5788(2) 0.0557(12) Uani 1 1 d . . C14' C -0.0425(7) 0.5020(4) 0.5784(2) 0.0555(12) Uani 1 1 d . . H14' H -0.0121 0.5727 0.5735 0.067 Uiso 1 1 calc R . C15' C 0.0939(6) 0.4213(3) 0.5847(2) 0.0496(11) Uani 1 1 d . . H15' H 0.2141 0.4377 0.5837 0.060 Uiso 1 1 calc R . C16' C -0.3687(8) 0.5724(4) 0.5704(3) 0.0750(16) Uani 1 1 d . . H16D H -0.3943 0.5970 0.5267 0.112 Uiso 1 1 calc GR . H16E H -0.3293 0.6307 0.5869 0.112 Uiso 1 1 calc GR . H16F H -0.4761 0.5470 0.5921 0.112 Uiso 1 1 calc GR . C17' C 0.2258(5) 0.0298(3) 0.59550(19) 0.0385(9) Uani 1 1 d . . C18' C 0.3503(6) -0.1542(3) 0.6079(2) 0.0523(11) Uani 1 1 d . . H18' H 0.3856 -0.2186 0.6352 0.063 Uiso 1 1 calc R . C19' C 0.3671(6) -0.1474(3) 0.5470(2) 0.0509(11) Uani 1 1 d . . H19' H 0.4206 -0.2052 0.5317 0.061 Uiso 1 1 calc R . C20' C 0.3030(5) -0.0514(3) 0.5048(2) 0.0429(10) Uani 1 1 d . . C21' C 0.2264(5) 0.0365(3) 0.52932(18) 0.0381(9) Uani 1 1 d . . C22' C 0.1452(5) 0.1262(3) 0.4877(2) 0.0462(10) Uani 1 1 d . . H22' H 0.0896 0.1833 0.5032 0.055 Uiso 1 1 calc R . C23' C 0.1468(6) 0.1308(4) 0.4244(2) 0.0536(12) Uani 1 1 d . . H23' H 0.0915 0.1902 0.3974 0.064 Uiso 1 1 calc R . C24' C 0.2317(6) 0.0460(4) 0.4007(2) 0.0577(13) Uani 1 1 d . . H24' H 0.2369 0.0505 0.3578 0.069 Uiso 1 1 calc R . C25' C 0.3062(6) -0.0423(4) 0.4396(2) 0.0514(11) Uani 1 1 d . . H25' H 0.3609 -0.0984 0.4231 0.062 Uiso 1 1 calc R . N1' N 0.2815(5) -0.0675(3) 0.63132(16) 0.0469(9) Uani 1 1 d . . H1' H 0.2730 -0.0752 0.6712 0.056 Uiso 1 1 calc R . O1' O 0.1151(4) -0.0036(2) 0.72400(14) 0.0554(8) Uani 1 1 d . . O2' O 0.3447(4) 0.2474(2) 0.57099(15) 0.0554(8) 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 0.0575(3) 0.0707(4) 0.1186(5) -0.0331(3) -0.0098(3) -0.0120(3) C1 0.048(3) 0.050(3) 0.052(3) -0.013(2) -0.011(2) 0.005(2) C2 0.059(3) 0.053(3) 0.061(3) -0.027(2) -0.010(2) 0.013(2) C3 0.053(3) 0.074(4) 0.057(3) -0.026(3) -0.003(2) 0.014(3) C4 0.051(3) 0.074(3) 0.046(3) -0.004(2) 0.003(2) -0.011(3) C5 0.053(3) 0.047(3) 0.036(2) -0.012(2) -0.0077(19) 0.008(2) C6 0.045(2) 0.044(2) 0.039(2) -0.0110(19) -0.0065(18) 0.007(2) C7 0.045(2) 0.035(2) 0.051(3) -0.010(2) -0.002(2) 0.004(2) C8 0.043(2) 0.036(2) 0.043(2) -0.0102(19) -0.0005(19) 0.0040(19) C9 0.046(2) 0.041(2) 0.039(2) -0.0091(19) 0.0008(19) 0.002(2) C10 0.043(2) 0.041(2) 0.041(2) -0.0103(19) -0.0057(18) 0.005(2) C11 0.048(3) 0.047(3) 0.058(3) -0.010(2) -0.007(2) 0.003(2) C12 0.072(4) 0.041(3) 0.065(3) -0.008(2) -0.011(3) -0.006(2) C13 0.071(3) 0.045(3) 0.046(3) -0.016(2) -0.017(2) 0.011(3) C14 0.051(3) 0.062(3) 0.062(3) -0.024(3) -0.018(2) 0.020(3) C15 0.048(3) 0.051(3) 0.056(3) -0.019(2) -0.005(2) -0.002(2) C16 0.107(5) 0.050(3) 0.068(4) -0.016(3) -0.025(3) 0.020(3) C17 0.045(2) 0.038(2) 0.049(3) -0.011(2) 0.002(2) -0.002(2) C18 0.042(3) 0.049(3) 0.085(4) -0.018(3) 0.002(2) 0.010(2) C19 0.048(3) 0.051(3) 0.081(4) -0.031(3) 0.019(3) 0.001(2) C20 0.046(3) 0.049(3) 0.063(3) -0.023(2) 0.017(2) -0.014(2) C21 0.041(2) 0.046(3) 0.049(3) -0.015(2) 0.009(2) -0.008(2) C22 0.056(3) 0.054(3) 0.045(3) -0.013(2) 0.010(2) -0.006(2) C23 0.069(3) 0.069(3) 0.052(3) -0.006(3) 0.002(2) -0.012(3) C24 0.079(4) 0.088(4) 0.051(3) -0.029(3) 0.023(3) -0.029(3) C25 0.057(3) 0.063(3) 0.073(4) -0.034(3) 0.025(3) -0.018(3) N1 0.048(2) 0.051(2) 0.049(2) -0.0127(18) -0.0015(17) 0.0097(18) O1 0.055(2) 0.067(2) 0.057(2) -0.0198(16) -0.0182(16) 0.0237(17) O2 0.0549(19) 0.0474(18) 0.061(2) -0.0181(15) -0.0083(15) -0.0051(15) Br1' 0.0770(4) 0.1311(6) 0.0907(5) -0.0259(4) 0.0258(3) 0.0128(4) C1' 0.103(4) 0.058(3) 0.048(3) -0.010(2) 0.005(3) 0.021(3) C2' 0.157(6) 0.079(4) 0.054(3) -0.020(3) 0.017(4) 0.033(4) C3' 0.191(7) 0.060(4) 0.073(4) -0.024(3) -0.007(5) 0.011(4) C4' 0.173(6) 0.072(4) 0.076(4) -0.029(3) -0.026(4) -0.023(4) C5' 0.143(5) 0.052(3) 0.056(3) -0.003(2) -0.021(3) -0.006(3) C6' 0.096(4) 0.048(3) 0.038(2) -0.009(2) -0.007(2) 0.019(2) C7' 0.044(2) 0.039(3) 0.050(3) -0.013(2) -0.003(2) 0.004(2) C8' 0.042(2) 0.029(2) 0.048(3) -0.0107(18) 0.0002(19) 0.0042(18) C9' 0.047(3) 0.040(2) 0.041(2) -0.0136(19) -0.0029(19) -0.002(2) C10' 0.049(3) 0.039(2) 0.038(2) -0.0127(19) 0.0004(19) -0.002(2) C11' 0.054(3) 0.036(2) 0.060(3) -0.011(2) 0.001(2) -0.004(2) C12' 0.046(3) 0.053(3) 0.061(3) -0.010(2) -0.006(2) 0.005(2) C13' 0.075(4) 0.045(3) 0.045(3) -0.012(2) -0.002(2) 0.017(3) C14' 0.076(4) 0.035(3) 0.057(3) -0.015(2) -0.002(2) 0.003(2) C15' 0.056(3) 0.038(3) 0.056(3) -0.011(2) 0.000(2) -0.004(2) C16' 0.085(4) 0.057(3) 0.076(4) -0.009(3) -0.008(3) 0.024(3) C17' 0.032(2) 0.034(2) 0.048(3) -0.0060(19) 0.0028(18) -0.0002(18) C18' 0.054(3) 0.033(2) 0.068(3) -0.010(2) 0.007(2) 0.005(2) C19' 0.050(3) 0.040(3) 0.066(3) -0.021(2) 0.006(2) 0.001(2) C20' 0.034(2) 0.043(2) 0.058(3) -0.022(2) 0.0053(19) -0.0067(19) C21' 0.036(2) 0.037(2) 0.044(2) -0.0144(19) 0.0053(18) -0.0060(18) C22' 0.040(2) 0.044(3) 0.055(3) -0.014(2) 0.001(2) 0.003(2) C23' 0.052(3) 0.057(3) 0.051(3) -0.011(2) -0.004(2) -0.001(2) C24' 0.061(3) 0.071(3) 0.045(3) -0.020(3) -0.004(2) -0.009(3) C25' 0.049(3) 0.057(3) 0.055(3) -0.028(2) 0.005(2) -0.006(2) N1' 0.055(2) 0.038(2) 0.047(2) -0.0094(17) 0.0069(17) 0.0016(17) O1' 0.071(2) 0.0410(18) 0.0495(18) -0.0037(15) 0.0107(15) 0.0051(15) O2' 0.0471(18) 0.0441(18) 0.074(2) -0.0110(15) 0.0133(16) -0.0049(15) 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 C2 C1 Br1 117.9(3) C2 C1 C6 121.4(4) C6 C1 Br1 120.7(3) C1 C2 H2 120.3 C3 C2 C1 119.3(4) C3 C2 H2 120.3 C2 C3 H3 119.6 C2 C3 C4 120.7(5) C4 C3 H3 119.6 C3 C4 H4 119.3 C5 C4 C3 121.3(5) C5 C4 H4 119.3 C4 C5 H5 120.7 C4 C5 C6 118.7(4) C6 C5 H5 120.7 C1 C6 C5 118.5(4) C1 C6 C7 121.6(4) C5 C6 C7 119.9(4) C8 C7 C6 117.8(4) O1 C7 C6 116.9(4) O1 C7 C8 125.1(4) C7 C8 C9 116.7(4) C17 C8 C7 120.7(4) C17 C8 C9 121.5(4) C10 C9 C8 119.0(4) O2 C9 C8 121.3(4) O2 C9 C10 119.7(4) C11 C10 C9 121.0(4) C11 C10 C15 118.4(4) C15 C10 C9 120.5(4) C10 C11 H11 119.6 C10 C11 C12 120.7(4) C12 C11 H11 119.6 C11 C12 H12 119.2 C11 C12 C13 121.7(5) C13 C12 H12 119.2 C12 C13 C16 120.8(5) C14 C13 C12 116.8(4) C14 C13 C16 122.4(5) C13 C14 H14 118.8 C13 C14 C15 122.5(4) C15 C14 H14 118.8 C10 C15 H15 120.1 C14 C15 C10 119.9(4) C14 C15 H15 120.1 C13 C16 H16A 109.5 C13 C16 H16B 109.5 C13 C16 H16C 109.5 H16A C16 H16B 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C8 C17 C21 126.1(4) N1 C17 C8 119.1(4) N1 C17 C21 114.8(4) C19 C18 H18 119.9 C19 C18 N1 120.3(5) N1 C18 H18 119.9 C18 C19 H19 119.9 C18 C19 C20 120.2(4) C20 C19 H19 119.9 C19 C20 C21 119.3(4) C19 C20 C25 121.9(4) C25 C20 C21 118.8(5) C20 C21 C17 118.9(4) C22 C21 C17 122.5(4) C22 C21 C20 118.5(4) C21 C22 H22 119.5 C23 C22 C21 121.1(4) C23 C22 H22 119.5 C22 C23 H23 120.4 C22 C23 C24 119.2(5) C24 C23 H23 120.4 C23 C24 H24 119.3 C25 C24 C23 121.4(5) C25 C24 H24 119.3 C20 C25 H25 119.6 C24 C25 C20 120.7(5) C24 C25 H25 119.6 C17 N1 C18 125.5(4) C17 N1 H1 117.3 C18 N1 H1 117.3 C2' C1' Br1' 117.7(5) C6' C1' Br1' 121.9(4) C6' C1' C2' 120.4(6) C1' C2' H2' 121.5 C3' C2' C1' 116.9(7) C3' C2' H2' 121.5 C2' C3' H3' 117.9 C2' C3' C4' 124.2(7) C4' C3' H3' 117.9 C3' C4' H4' 119.2 C5' C4' C3' 121.7(7) C5' C4' H4' 119.2 C4' C5' H5' 121.9 C4' C5' C6' 116.2(7) C6' C5' H5' 121.9 C1' C6' C5' 120.5(5) C1' C6' C7' 121.5(5) C5' C6' C7' 117.8(5) C8' C7' C6' 119.6(4) O1' C7' C6' 115.3(4) O1' C7' C8' 125.0(4) C7' C8' C9' 120.6(3) C7' C8' C17' 120.9(4) C17' C8' C9' 117.3(4) C8' C9' C10' 120.2(4) O2' C9' C8' 120.3(4) O2' C9' C10' 119.5(4) C11' C10' C9' 121.8(4) C11' C10' C15' 118.0(4) C15' C10' C9' 120.1(4) C10' C11' H11' 119.2 C10' C11' C12' 121.6(4) C12' C11' H11' 119.2 C11' C12' H12' 119.8 C11' C12' C13' 120.4(5) C13' C12' H12' 119.8 C12' C13' C16' 120.8(5) C14' C13' C12' 117.8(4) C14' C13' C16' 121.4(5) C13' C14' H14' 118.8 C15' C14' C13' 122.5(4) C15' C14' H14' 118.8 C10' C15' H15' 120.1 C14' C15' C10' 119.8(4) C14' C15' H15' 120.1 C13' C16' H16D 109.5 C13' C16' H16E 109.5 C13' C16' H16F 109.5 H16D C16' H16E 109.5 H16D C16' H16F 109.5 H16E C16' H16F 109.5 C21' C17' C8' 126.7(4) N1' C17' C8' 117.1(4) N1' C17' C21' 116.2(3) C19' C18' H18' 119.6 C19' C18' N1' 120.8(4) N1' C18' H18' 119.6 C18' C19' H19' 120.1 C18' C19' C20' 119.8(4) C20' C19' H19' 120.1 C21' C20' C19' 118.9(4) C25' C20' C19' 122.3(4) C25' C20' C21' 118.8(4) C20' C21' C17' 119.6(4) C22' C21' C17' 121.9(4) C22' C21' C20' 118.4(4) C21' C22' H22' 119.5 C23' C22' C21' 120.9(4) C23' C22' H22' 119.5 C22' C23' H23' 120.0 C22' C23' C24' 119.9(4) C24' C23' H23' 120.0 C23' C24' H24' 119.8 C25' C24' C23' 120.4(4) C25' C24' H24' 119.8 C20' C25' H25' 119.3 C24' C25' C20' 121.5(4) C24' C25' H25' 119.3 C17' N1' C18' 124.2(4) C17' N1' H1' 117.9 C18' N1' H1' 117.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C1 1.895(5) C1 C2 1.383(6) C1 C6 1.385(6) C2 H2 0.9300 C2 C3 1.363(7) C3 H3 0.9300 C3 C4 1.376(7) C4 H4 0.9300 C4 C5 1.370(6) C5 H5 0.9300 C5 C6 1.424(6) C6 C7 1.513(6) C7 C8 1.425(6) C7 O1 1.254(5) C8 C9 1.496(6) C8 C17 1.416(6) C9 C10 1.496(6) C9 O2 1.216(5) C10 C11 1.380(6) C10 C15 1.389(6) C11 H11 0.9300 C11 C12 1.387(6) C12 H12 0.9300 C12 C13 1.388(7) C13 C14 1.378(7) C13 C16 1.498(6) C14 H14 0.9300 C14 C15 1.389(6) C15 H15 0.9300 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C17 C21 1.466(6) C17 N1 1.352(5) C18 H18 0.9300 C18 C19 1.333(7) C18 N1 1.360(5) C19 H19 0.9300 C19 C20 1.405(7) C20 C21 1.417(6) C20 C25 1.413(6) C21 C22 1.411(6) C22 H22 0.9300 C22 C23 1.381(6) C23 H23 0.9300 C23 C24 1.394(7) C24 H24 0.9300 C24 C25 1.355(7) C25 H25 0.9300 N1 H1 0.8600 Br1' C1' 1.876(6) C1' C2' 1.430(8) C1' C6' 1.381(7) C2' H2' 0.9300 C2' C3' 1.354(10) C3' H3' 0.9300 C3' C4' 1.376(10) C4' H4' 0.9300 C4' C5' 1.363(8) C5' H5' 0.9300 C5' C6' 1.475(8) C6' C7' 1.506(6) C7' C8' 1.400(6) C7' O1' 1.258(5) C8' C9' 1.492(6) C8' C17' 1.439(5) C9' C10' 1.492(6) C9' O2' 1.222(5) C10' C11' 1.375(6) C10' C15' 1.399(6) C11' H11' 0.9300 C11' C12' 1.383(6) C12' H12' 0.9300 C12' C13' 1.386(6) C13' C14' 1.373(7) C13' C16' 1.503(6) C14' H14' 0.9300 C14' C15' 1.372(6) C15' H15' 0.9300 C16' H16D 0.9600 C16' H16E 0.9600 C16' H16F 0.9600 C17' C21' 1.435(6) C17' N1' 1.360(5) C18' H18' 0.9300 C18' C19' 1.324(6) C18' N1' 1.374(5) C19' H19' 0.9300 C19' C20' 1.425(6) C20' C21' 1.417(5) C20' C25' 1.410(6) C21' C22' 1.406(6) C22' H22' 0.9300 C22' C23' 1.378(6) C23' H23' 0.9300 C23' C24' 1.396(6) C24' H24' 0.9300 C24' C25' 1.349(6) C25' H25' 0.9300 N1' H1' 0.8600 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 N1 H1 O1 0.86 1.89 2.590(5) 137.7 N1' H1' O1' 0.86 1.94 2.596(5) 132.1 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 Br1 C1 C2 C3 176.7(3) Br1 C1 C6 C5 -179.2(3) Br1 C1 C6 C7 3.5(6) C1 C2 C3 C4 1.7(7) C1 C6 C7 C8 -116.7(4) C1 C6 C7 O1 68.2(5) C2 C1 C6 C5 -1.7(6) C2 C1 C6 C7 -179.1(4) C2 C3 C4 C5 0.0(7) C3 C4 C5 C6 -2.6(7) C4 C5 C6 C1 3.4(6) C4 C5 C6 C7 -179.3(4) C5 C6 C7 C8 66.0(5) C5 C6 C7 O1 -109.1(5) C6 C1 C2 C3 -0.8(7) C6 C7 C8 C9 -5.4(5) C6 C7 C8 C17 -173.8(4) C7 C8 C9 C10 67.5(5) C7 C8 C9 O2 -114.5(4) C7 C8 C17 C21 -171.7(4) C7 C8 C17 N1 8.4(6) C8 C9 C10 C11 30.0(6) C8 C9 C10 C15 -152.8(4) C8 C17 C21 C20 -169.2(4) C8 C17 C21 C22 12.9(6) C8 C17 N1 C18 171.9(4) C9 C8 C17 C21 20.5(6) C9 C8 C17 N1 -159.4(4) C9 C10 C11 C12 175.2(4) C9 C10 C15 C14 -176.6(4) C10 C11 C12 C13 1.9(7) C11 C10 C15 C14 0.6(6) C11 C12 C13 C14 -0.3(7) C11 C12 C13 C16 -178.8(4) C12 C13 C14 C15 -1.1(7) C13 C14 C15 C10 0.9(7) C15 C10 C11 C12 -2.0(6) C16 C13 C14 C15 177.4(4) C17 C8 C9 C10 -124.2(4) C17 C8 C9 O2 53.8(6) C17 C21 C22 C23 -177.9(4) C18 C19 C20 C21 -3.4(7) C18 C19 C20 C25 175.6(4) C19 C18 N1 C17 -0.7(7) C19 C20 C21 C17 -5.5(6) C19 C20 C21 C22 172.5(4) C19 C20 C25 C24 -174.5(4) C20 C21 C22 C23 4.2(6) C21 C17 N1 C18 -8.0(6) C21 C20 C25 C24 4.5(7) C21 C22 C23 C24 0.5(7) C22 C23 C24 C25 -2.7(7) C23 C24 C25 C20 0.2(7) C25 C20 C21 C17 175.4(4) C25 C20 C21 C22 -6.6(6) N1 C17 C21 C20 10.7(6) N1 C17 C21 C22 -167.2(4) N1 C18 C19 C20 6.8(7) O1 C7 C8 C9 169.2(4) O1 C7 C8 C17 0.8(7) O2 C9 C10 C11 -147.9(4) O2 C9 C10 C15 29.2(6) Br1' C1' C2' C3' 179.1(5) Br1' C1' C6' C5' -177.7(3) Br1' C1' C6' C7' -3.3(7) C1' C2' C3' C4' -1.6(10) C1' C6' C7' C8' 117.6(5) C1' C6' C7' O1' -66.1(6) C2' C1' C6' C5' 3.1(7) C2' C1' C6' C7' 177.5(4) C2' C3' C4' C5' 3.4(11) C3' C4' C5' C6' -1.8(9) C4' C5' C6' C1' -1.3(7) C4' C5' C6' C7' -175.9(5) C5' C6' C7' C8' -67.9(5) C5' C6' C7' O1' 108.4(5) C6' C1' C2' C3' -1.7(8) C6' C7' C8' C9' 8.7(6) C6' C7' C8' C17' 175.7(4) C7' C8' C9' C10' -58.9(5) C7' C8' C9' O2' 122.7(4) C7' C8' C17' C21' 158.4(4) C7' C8' C17' N1' -19.2(6) C8' C9' C10' C11' -28.1(6) C8' C9' C10' C15' 156.6(4) C8' C17' C21' C20' 174.9(4) C8' C17' C21' C22' -8.2(6) C8' C17' N1' C18' -176.6(4) C9' C8' C17' C21' -34.2(6) C9' C8' C17' N1' 148.1(4) C9' C10' C11' C12' -175.6(4) C9' C10' C15' C14' 176.2(4) C10' C11' C12' C13' -0.3(7) C11' C10' C15' C14' 0.8(6) C11' C12' C13' C14' 0.4(7) C11' C12' C13' C16' 179.2(4) C12' C13' C14' C15' 0.2(7) C13' C14' C15' C10' -0.8(7) C15' C10' C11' C12' -0.3(6) C16' C13' C14' C15' -178.7(5) C17' C8' C9' C10' 133.7(4) C17' C8' C9' O2' -44.7(5) C17' C21' C22' C23' -179.8(4) C18' C19' C20' C21' 1.7(6) C18' C19' C20' C25' -175.6(4) C19' C18' N1' C17' 0.1(7) C19' C20' C21' C17' 4.1(6) C19' C20' C21' C22' -172.9(4) C19' C20' C25' C24' 174.6(4) C20' C21' C22' C23' -2.8(6) C21' C17' N1' C18' 5.5(6) C21' C20' C25' C24' -2.8(6) C21' C22' C23' C24' -0.7(6) C22' C23' C24' C25' 2.5(7) C23' C24' C25' C20' -0.8(7) C25' C20' C21' C17' -178.5(4) C25' C20' C21' C22' 4.5(6) N1' C17' C21' C20' -7.4(5) N1' C17' C21' C22' 169.5(4) N1' C18' C19' C20' -3.9(7) O1' C7' C8' C9' -167.2(4) O1' C7' C8' C17' -0.3(7) O2' C9' C10' C11' 150.3(4) O2' C9' C10' C15' -25.0(6)