#------------------------------------------------------------------------------ #$Date: 2020-07-06 04:53:51 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253799 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126527.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_7126527 loop_ _publ_author_name 'Cui, Yunshu' 'Xiang, Libo' 'Wang, Junyi' 'Li, Chunlei' 'Hao, Wei' 'Ye, Qing' _publ_section_title ; Storage and release of two electrons from an electron-rich carbon-carbon bond: boron mediated reversible coupling of DMAP and 9-azajulolidine. ; _journal_issue 50 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 6794 _journal_page_last 6797 _journal_paper_doi 10.1039/d0cc01575j _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C47 H54 B N4, 4(C H2 Cl2), Br' _chemical_formula_sum 'C51 H62 B Br Cl8 N4' _chemical_formula_weight 1105.36 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2020-02-27 deposited with the CCDC. 2020-05-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 112.512(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.7601(16) _cell_length_b 13.8832(11) _cell_length_c 22.628(2) _cell_measurement_reflns_used 9840 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.35 _cell_measurement_theta_min 2.31 _cell_volume 5444.4(8) _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1064 _diffrn_reflns_av_unetI/netI 0.0679 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 75216 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.463 _diffrn_reflns_theta_min 2.315 _exptl_absorpt_coefficient_mu 1.185 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0840 before and 0.0648 after correction. The Ratio of minimum to maximum transmission is 0.8163. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear yellowish orange' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier yellowish _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.344 _exptl_crystal_description block _exptl_crystal_F_000 2272 _exptl_crystal_size_max 0.258 _exptl_crystal_size_mid 0.208 _exptl_crystal_size_min 0.083 _refine_diff_density_max 1.823 _refine_diff_density_min -1.371 _refine_diff_density_rms 0.085 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 604 _refine_ls_number_reflns 11207 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.145 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0567 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1638 _refine_ls_wR_factor_ref 0.1789 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7868 _reflns_number_total 11207 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc01575j2.cif _cod_data_source_block 6 _cod_depositor_comments 'Adding full bibliography for 7126523--7126527.cif.' _cod_original_cell_volume 5444.3(8) _cod_original_sg_symbol_H-M 'P 21/c' _cod_original_formula_sum ' C51 H62 B Br Cl8 N4' _cod_database_code 7126527 _shelx_shelxl_version_number 2016/6 _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_res_file ; TITL YQ354_0m_a.res in P2(1)/c YQ354_0m_a.res created by SHELXL-2016/6 at 16:29:39 on 27-Dec-2019 REM Old TITL YQ354_0m in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.167, Rweak 0.017, Alpha 0.096, Orientation as input REM Formula found by SHELXT: C48 B4 Br Cl8 N4 CELL 0.71073 18.7601 13.8832 22.6278 90 112.512 90 ZERR 50 0.0016 0.0011 0.0021 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H B Br Cl N UNIT 204 232 4 4 32 16 L.S. 99 PLAN 25 TEMP -173.17 BOND $H LIST 6 fmap 2 acta MORE -1 CONF REM REM REM SAME 0.02 0.04 C7 C8A C9 SAME 0.02 0.04 C7 C8 C9 WGHT 0.100000 FVAR 0.17853 0.58446 BR01 4 0.978298 0.096884 0.681646 11.00000 0.02953 0.03369 = 0.02981 -0.00056 0.00786 -0.00394 CL1 5 0.941274 1.261031 0.488872 11.00000 0.16109 0.03654 = 0.13681 0.00727 0.09788 -0.00907 N1 6 0.865091 0.596179 0.617138 11.00000 0.02578 0.03675 = 0.02549 -0.00102 0.00435 0.00759 C1 1 0.841058 0.629364 0.668305 11.00000 0.03576 0.04928 = 0.02436 -0.00478 0.00754 0.01050 AFIX 23 H1A 2 0.885059 0.661575 0.701969 11.00000 -1.20000 H1B 2 0.826012 0.573149 0.687855 11.00000 -1.20000 AFIX 0 B1 3 0.666566 0.597799 0.356982 11.00000 0.01893 0.02192 = 0.02566 0.00009 0.00847 0.00053 CL2 5 0.896730 1.060125 0.468253 11.00000 0.08105 0.05034 = 0.04756 -0.00392 0.01947 -0.01648 N2 6 0.718245 0.597464 0.425804 11.00000 0.01930 0.02620 = 0.02348 0.00053 0.00811 0.00114 C2 1 0.774381 0.698211 0.643297 11.00000 0.03376 0.03576 = 0.02935 -0.00366 0.01362 0.00271 AFIX 23 H2A 2 0.791610 0.758835 0.629884 11.00000 -1.20000 H2B 2 0.755897 0.713710 0.677721 11.00000 -1.20000 AFIX 0 CL3 5 0.797949 0.403777 0.773788 11.00000 0.05627 0.04524 = 0.07447 0.00087 0.03085 0.00596 N3 6 0.689863 0.601134 0.303485 11.00000 0.01925 0.02423 = 0.02164 -0.00164 0.00606 -0.00012 C3 1 0.708991 0.654851 0.586943 11.00000 0.02838 0.03907 = 0.02578 -0.00374 0.01063 -0.00063 AFIX 23 H3A 2 0.667219 0.702802 0.568676 11.00000 -1.20000 H3B 2 0.687577 0.598276 0.601130 11.00000 -1.20000 AFIX 0 CL4 5 0.929501 0.294944 0.769553 11.00000 0.04191 0.04829 = 0.04108 -0.00923 0.01770 -0.00569 N4 6 0.583987 0.591955 0.332673 11.00000 0.02115 0.02224 = 0.02403 0.00150 0.00906 0.00063 C4 1 0.739723 0.624548 0.536705 11.00000 0.02259 0.02248 = 0.02473 0.00210 0.00789 0.00023 C5 1 0.817671 0.596733 0.555815 11.00000 0.02482 0.02408 = 0.02447 -0.00120 0.00797 -0.00099 CL5 5 0.774780 0.184118 0.544361 11.00000 0.09566 0.05200 = 0.07153 -0.01124 -0.01521 -0.00304 C6 1 0.844083 0.567821 0.506855 11.00000 0.02284 0.03425 = 0.02538 -0.00217 0.00691 0.00324 CL6 5 0.779603 0.369455 0.603199 11.00000 0.06862 0.05471 = 0.07786 -0.01365 -0.00428 0.02279 C7 1 0.925704 0.535217 0.524031 11.00000 0.02607 0.06499 = 0.03143 -0.00844 0.00407 0.01071 AFIX 23 H7A 2 0.926919 0.483653 0.494210 11.00000 -1.20000 H7B 2 0.956934 0.589808 0.519104 11.00000 -1.20000 AFIX 0 CL8 5 0.908794 -0.166413 0.573271 11.00000 0.04046 0.04803 = 0.05264 0.00884 0.01360 0.00133 CL7 5 0.753388 -0.088702 0.530881 11.00000 0.04095 0.04882 = 0.05537 0.00986 0.01144 0.00057 C9 1 0.945168 0.560911 0.638457 11.00000 0.02877 0.07113 = 0.03388 -0.00461 0.00260 0.01976 AFIX 23 H9A 2 0.957247 0.522874 0.678124 11.00000 -1.20000 H9B 2 0.980592 0.616832 0.648754 11.00000 -1.20000 AFIX 0 C10 1 0.793913 0.570249 0.444923 11.00000 0.02356 0.02957 = 0.02736 0.00111 0.00851 0.00558 AFIX 43 H10 2 0.812400 0.551964 0.412893 11.00000 -1.20000 AFIX 0 C11 1 0.693164 0.624672 0.473268 11.00000 0.02042 0.02474 = 0.02838 0.00125 0.00803 -0.00108 AFIX 43 H11 2 0.641013 0.644428 0.461218 11.00000 -1.20000 AFIX 0 C12 1 0.763218 0.618416 0.298778 11.00000 0.02140 0.02674 = 0.02001 0.00310 0.00598 0.00023 C13 1 0.797834 0.709450 0.316700 11.00000 0.02540 0.02854 = 0.02108 0.00041 0.00646 -0.00169 C14 1 0.868111 0.725687 0.311037 11.00000 0.02852 0.03279 = 0.02780 0.00270 0.00815 -0.00730 AFIX 43 H14 2 0.892949 0.786326 0.322992 11.00000 -1.20000 AFIX 0 C15 1 0.902151 0.654112 0.288098 11.00000 0.02396 0.04094 = 0.03506 0.00915 0.01119 -0.00180 AFIX 43 H15 2 0.949941 0.666617 0.284188 11.00000 -1.20000 AFIX 0 C16 1 0.868001 0.565162 0.270855 11.00000 0.02564 0.03842 = 0.03021 0.00819 0.01299 0.00789 AFIX 43 H16 2 0.892335 0.517261 0.255094 11.00000 -1.20000 AFIX 0 C17 1 0.797601 0.544696 0.276368 11.00000 0.02469 0.02907 = 0.02373 0.00165 0.00538 0.00041 C18 1 0.762734 0.444626 0.261539 11.00000 0.02538 0.02786 = 0.04097 -0.00199 0.01246 0.00041 AFIX 13 H18 2 0.706487 0.450151 0.252942 11.00000 -1.20000 AFIX 0 C19 1 0.799178 0.377671 0.319096 11.00000 0.07719 0.03305 = 0.04948 -0.00361 0.02607 -0.00569 AFIX 137 H19A 2 0.775634 0.313664 0.308735 11.00000 -1.50000 H19B 2 0.790458 0.403866 0.355987 11.00000 -1.50000 H19C 2 0.854761 0.372641 0.329394 11.00000 -1.50000 AFIX 0 C20 1 0.770370 0.400769 0.202245 11.00000 0.04189 0.04025 = 0.04439 -0.01137 0.01340 -0.00173 AFIX 137 H20A 2 0.744541 0.337991 0.193156 11.00000 -1.50000 H20B 2 0.825104 0.392496 0.209996 11.00000 -1.50000 H20C 2 0.746359 0.443714 0.165584 11.00000 -1.50000 AFIX 0 C21 1 0.758366 0.789877 0.338378 11.00000 0.03695 0.02918 = 0.03842 -0.00574 0.02108 -0.00819 AFIX 13 H21 2 0.727293 0.759083 0.360603 11.00000 -1.20000 AFIX 0 C22 1 0.814347 0.859471 0.385503 11.00000 0.06238 0.04881 = 0.04674 -0.01517 0.01465 -0.00060 AFIX 137 H22A 2 0.841262 0.896864 0.363641 11.00000 -1.50000 H22B 2 0.852065 0.823123 0.420796 11.00000 -1.50000 H22C 2 0.785766 0.903242 0.402416 11.00000 -1.50000 AFIX 0 C23 1 0.702791 0.844876 0.281570 11.00000 0.04901 0.04522 = 0.06009 -0.01591 0.00313 0.01797 AFIX 137 H23A 2 0.731706 0.878480 0.259761 11.00000 -1.50000 H23B 2 0.674383 0.891942 0.296393 11.00000 -1.50000 H23C 2 0.666342 0.799775 0.251814 11.00000 -1.50000 AFIX 0 C24 1 0.529475 0.581370 0.362601 11.00000 0.01875 0.02192 = 0.02472 -0.00157 0.00598 -0.00149 C25 1 0.520568 0.489675 0.385784 11.00000 0.02775 0.02377 = 0.02750 -0.00032 0.00821 -0.00248 C26 1 0.468546 0.480886 0.414482 11.00000 0.03217 0.03219 = 0.03958 0.00426 0.01491 -0.00542 AFIX 43 H26 2 0.461751 0.420099 0.430888 11.00000 -1.20000 AFIX 0 C27 1 0.425514 0.559306 0.420032 11.00000 0.03047 0.04734 = 0.03978 -0.00057 0.02011 -0.00320 AFIX 43 H27 2 0.390420 0.551955 0.440827 11.00000 -1.20000 AFIX 0 C28 1 0.433581 0.648834 0.395212 11.00000 0.02647 0.03884 = 0.03933 -0.00367 0.01293 0.00253 AFIX 43 H28 2 0.402728 0.701425 0.398189 11.00000 -1.20000 AFIX 0 C29 1 0.486168 0.662130 0.366175 11.00000 0.02351 0.02483 = 0.02638 0.00013 0.00700 0.00123 C30 1 0.563915 0.402656 0.375932 11.00000 0.03687 0.02001 = 0.04123 0.00251 0.01789 -0.00288 AFIX 13 H30 2 0.600294 0.425678 0.356220 11.00000 -1.20000 AFIX 0 C31 1 0.611660 0.352737 0.439164 11.00000 0.06262 0.03864 = 0.04555 -0.00010 0.00845 0.01892 AFIX 137 H31A 2 0.638443 0.297096 0.430652 11.00000 -1.50000 H31B 2 0.577431 0.331074 0.460108 11.00000 -1.50000 H31C 2 0.649637 0.398118 0.467170 11.00000 -1.50000 AFIX 0 C32 1 0.507668 0.332406 0.329371 11.00000 0.05456 0.03532 = 0.04381 -0.00608 0.01397 -0.00050 AFIX 137 H32A 2 0.477554 0.366077 0.289530 11.00000 -1.50000 H32B 2 0.472780 0.306449 0.348431 11.00000 -1.50000 H32C 2 0.536507 0.279526 0.320216 11.00000 -1.50000 AFIX 0 C33 1 0.496384 0.759265 0.339212 11.00000 0.03069 0.02615 = 0.03238 0.00095 0.01240 0.00679 AFIX 13 H33 2 0.516230 0.746764 0.304730 11.00000 -1.20000 AFIX 0 C34 1 0.555552 0.821528 0.389577 11.00000 0.04675 0.02802 = 0.04594 0.00386 0.00547 -0.00455 AFIX 137 H34A 2 0.605946 0.789543 0.404628 11.00000 -1.50000 H34B 2 0.539606 0.831077 0.425651 11.00000 -1.50000 H34C 2 0.559260 0.884116 0.370929 11.00000 -1.50000 AFIX 0 C35 1 0.420843 0.814999 0.309218 11.00000 0.04181 0.03555 = 0.06833 0.00996 0.00477 0.01105 AFIX 137 H35A 2 0.429408 0.872587 0.287764 11.00000 -1.50000 H35B 2 0.402608 0.834174 0.342701 11.00000 -1.50000 H35C 2 0.382027 0.774011 0.277936 11.00000 -1.50000 AFIX 0 C36 1 0.621426 0.596212 0.248883 11.00000 0.02336 0.01849 = 0.02561 -0.00023 0.00535 0.00002 C37 1 0.595910 0.596714 0.179440 11.00000 0.02730 0.01785 = 0.02345 -0.00152 0.00481 -0.00080 C38 1 0.627893 0.605943 0.134317 11.00000 0.03127 0.02737 = 0.03028 -0.00168 0.00916 0.00039 AFIX 43 H38 2 0.682069 0.612401 0.146490 11.00000 -1.20000 AFIX 0 C39 1 0.576800 0.605508 0.068234 11.00000 0.04410 0.03878 = 0.02519 -0.00194 0.01179 0.00377 AFIX 43 H39 2 0.598680 0.610595 0.036812 11.00000 -1.20000 AFIX 0 C40 1 0.498698 0.598212 0.048037 11.00000 0.03951 0.03425 = 0.02507 -0.00281 0.00427 0.00319 AFIX 43 H40 2 0.467404 0.599510 0.003642 11.00000 -1.20000 AFIX 0 C41 1 0.464060 0.588570 0.094164 11.00000 0.03035 0.01942 = 0.03078 -0.00342 0.00245 0.00120 C42 1 0.513672 0.588312 0.157978 11.00000 0.02645 0.01992 = 0.02804 -0.00220 0.00747 -0.00071 C43 1 0.488417 0.583179 0.209680 11.00000 0.02496 0.01672 = 0.02859 0.00128 0.00581 -0.00035 C44 1 0.410746 0.577011 0.196599 11.00000 0.02708 0.02224 = 0.03735 0.00404 0.00637 -0.00034 AFIX 43 H44 2 0.392043 0.573517 0.230068 11.00000 -1.20000 AFIX 0 C45 1 0.359345 0.576031 0.131415 11.00000 0.02342 0.02684 = 0.04476 -0.00177 0.00211 -0.00435 AFIX 43 H45 2 0.305524 0.571322 0.121752 11.00000 -1.20000 AFIX 0 C46 1 0.384161 0.581603 0.081750 11.00000 0.02915 0.02701 = 0.03404 0.00194 -0.00266 -0.00344 AFIX 43 H46 2 0.347628 0.580787 0.038856 11.00000 -1.20000 AFIX 0 C47 1 0.560062 0.589068 0.266276 11.00000 0.02056 0.01918 = 0.02754 -0.00047 0.00569 0.00014 C48 1 0.963278 1.143270 0.518232 11.00000 0.06595 0.04475 = 0.04760 -0.00716 0.02446 -0.01524 AFIX 23 H48A 2 0.962677 1.139769 0.561737 11.00000 -1.20000 H48B 2 1.015835 1.126314 0.521288 11.00000 -1.20000 AFIX 0 C49 1 0.898356 0.382953 0.810985 11.00000 0.04986 0.04860 = 0.04804 -0.01658 0.02024 -0.01126 AFIX 23 H49A 2 0.910988 0.361264 0.855535 11.00000 -1.20000 H49B 2 0.926326 0.443954 0.812481 11.00000 -1.20000 AFIX 0 C50 1 0.829564 0.266090 0.600325 11.00000 0.05658 0.04191 = 0.06097 -0.00432 0.00492 -0.00395 AFIX 23 H50A 2 0.874886 0.284081 0.590474 11.00000 -1.20000 H50B 2 0.848847 0.235197 0.643008 11.00000 -1.20000 AFIX 0 C51 1 0.849834 -0.076953 0.585837 11.00000 0.04601 0.04125 = 0.05022 -0.00571 0.01494 -0.01376 AFIX 23 H51A 2 0.869700 -0.012621 0.580974 11.00000 -1.20000 H51B 2 0.851564 -0.082134 0.630002 11.00000 -1.20000 AFIX 0 PART 1 C8A 1 0.959479 0.499405 0.589182 21.00000 0.02602 0.05202 = 0.03124 -0.00035 0.00515 0.01520 AFIX 23 H8A1 2 1.015897 0.493230 0.601372 21.00000 -1.20000 H8A2 2 0.938826 0.434113 0.590319 21.00000 -1.20000 AFIX 0 part 2 C8 1 0.975153 0.565807 0.591680 -21.00000 0.02512 0.05322 = 0.02550 -0.00362 -0.00407 0.01715 AFIX 23 H8A 2 1.022552 0.526022 0.606023 -21.00000 -1.20000 H8B 2 0.991217 0.633285 0.589797 -21.00000 -1.20000 part 0 AFIX 0 HKLF 4 REM YQ354_0m_a.res in P2(1)/c REM R1 = 0.0567 for 7868 Fo > 4sig(Fo) and 0.0880 for all 11207 data REM 604 parameters refined using 0 restraints END WGHT 0.0807 4.3665 REM Highest difference peak 1.823, deepest hole -1.371, 1-sigma level 0.085 Q1 1 0.7222 0.1995 0.5613 11.00000 0.05 1.82 Q2 1 0.8007 0.3805 0.5714 11.00000 0.05 1.30 Q3 1 0.7979 0.2454 0.5132 11.00000 0.05 0.68 Q4 1 0.9489 0.1650 0.6931 11.00000 0.05 0.68 Q5 1 0.9861 1.2618 0.5262 11.00000 0.05 0.52 Q6 1 0.7275 0.1437 0.5968 11.00000 0.05 0.50 Q7 1 0.7685 0.3923 0.7332 11.00000 0.05 0.46 Q8 1 0.9722 0.5735 0.6826 11.00000 0.05 0.42 Q9 1 0.7800 -0.0613 0.5719 11.00000 0.05 0.41 Q10 1 0.8806 1.1287 0.4684 11.00000 0.05 0.38 Q11 1 0.7255 0.6150 0.5567 11.00000 0.05 0.37 Q12 1 0.7996 0.2646 0.6275 11.00000 0.05 0.37 Q13 1 0.9422 0.5322 0.4925 11.00000 0.05 0.37 Q14 1 0.9794 0.7137 0.6816 11.00000 0.05 0.37 Q15 1 0.7208 0.6305 0.5053 11.00000 0.05 0.37 Q16 1 0.4794 0.5996 0.0706 11.00000 0.05 0.36 Q17 1 1.0084 0.0964 0.7338 11.00000 0.05 0.34 Q18 1 0.5665 0.5934 0.3016 11.00000 0.05 0.33 Q19 1 0.9377 0.4757 0.6471 11.00000 0.05 0.33 Q20 1 0.9146 0.4647 0.5278 11.00000 0.05 0.33 Q21 1 0.9678 0.5360 0.5741 11.00000 0.05 0.32 Q22 1 0.6158 0.6029 0.2220 11.00000 0.05 0.32 Q23 1 0.5924 0.6058 0.2573 11.00000 0.05 0.32 Q24 1 0.8280 0.5777 0.5312 11.00000 0.05 0.31 Q25 1 0.9308 0.4465 0.7852 11.00000 0.05 0.30 ; _shelx_res_checksum 70299 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Br01 Br 0.97830(2) 0.09688(2) 0.68165(2) 0.03205(13) Uani 1 1 d . . . . . Cl1 Cl 0.94127(12) 1.26103(9) 0.48887(9) 0.0993(6) Uani 1 1 d . . . . . N1 N 0.86509(17) 0.5962(2) 0.61714(13) 0.0310(7) Uani 1 1 d . . . . . C1 C 0.8411(2) 0.6294(3) 0.66831(17) 0.0377(9) Uani 1 1 d . . . . . H1A H 0.885059 0.661575 0.701969 0.045 Uiso 1 1 calc R U . . . H1B H 0.826012 0.573149 0.687855 0.045 Uiso 1 1 calc R U . . . B1 B 0.6666(2) 0.5978(2) 0.35698(18) 0.0222(7) Uani 1 1 d . . . . . Cl2 Cl 0.89673(8) 1.06013(8) 0.46825(5) 0.0612(3) Uani 1 1 d . . . . . N2 N 0.71825(15) 0.59746(18) 0.42580(13) 0.0230(6) Uani 1 1 d . . . . . C2 C 0.7744(2) 0.6982(3) 0.64330(16) 0.0325(8) Uani 1 1 d . . . . . H2A H 0.791610 0.758835 0.629884 0.039 Uiso 1 1 calc R U . . . H2B H 0.755897 0.713710 0.677721 0.039 Uiso 1 1 calc R U . . . Cl3 Cl 0.79795(7) 0.40378(7) 0.77379(6) 0.0569(3) Uani 1 1 d . . . . . N3 N 0.68986(15) 0.60113(17) 0.30349(12) 0.0222(6) Uani 1 1 d . . . . . C3 C 0.7090(2) 0.6549(3) 0.58694(16) 0.0310(8) Uani 1 1 d . . . . . H3A H 0.667219 0.702802 0.568676 0.037 Uiso 1 1 calc R U . . . H3B H 0.687577 0.598276 0.601130 0.037 Uiso 1 1 calc R U . . . Cl4 Cl 0.92950(6) 0.29494(7) 0.76955(5) 0.0432(2) Uani 1 1 d . . . . . N4 N 0.58399(15) 0.59196(17) 0.33267(13) 0.0224(6) Uani 1 1 d . . . . . C4 C 0.73972(18) 0.6245(2) 0.53670(15) 0.0236(7) Uani 1 1 d . . . . . C5 C 0.81767(19) 0.5967(2) 0.55582(16) 0.0249(7) Uani 1 1 d . . . . . Cl5 Cl 0.77478(9) 0.18412(9) 0.54436(7) 0.0872(5) Uani 1 1 d . . . . . C6 C 0.84408(19) 0.5678(2) 0.50685(16) 0.0282(7) Uani 1 1 d . . . . . Cl6 Cl 0.77960(8) 0.36946(9) 0.60320(7) 0.0767(4) Uani 1 1 d . . . . . C7 C 0.9257(2) 0.5352(3) 0.52403(18) 0.0429(10) Uani 1 1 d . . . . . H7A H 0.926919 0.483653 0.494210 0.051 Uiso 1 1 calc R U . A 1 H7B H 0.956934 0.589808 0.519104 0.051 Uiso 1 1 calc R U . A 1 Cl8 Cl 0.90879(6) -0.16641(7) 0.57327(5) 0.0483(3) Uani 1 1 d . . . . . Cl7 Cl 0.75339(6) -0.08870(7) 0.53088(5) 0.0505(3) Uani 1 1 d . . . . . C9 C 0.9452(2) 0.5609(3) 0.63846(19) 0.0474(11) Uani 1 1 d . . . . . H9A H 0.957247 0.522874 0.678124 0.057 Uiso 1 1 calc R U . B 1 H9B H 0.980592 0.616832 0.648754 0.057 Uiso 1 1 calc R U . B 1 C10 C 0.79391(19) 0.5702(2) 0.44492(16) 0.0272(7) Uani 1 1 d . . . . . H10 H 0.812400 0.551964 0.412893 0.033 Uiso 1 1 calc R U . . . C11 C 0.69316(19) 0.6247(2) 0.47327(15) 0.0249(7) Uani 1 1 d . . . . . H11 H 0.641013 0.644428 0.461218 0.030 Uiso 1 1 calc R U . . . C12 C 0.76322(18) 0.6184(2) 0.29878(15) 0.0233(7) Uani 1 1 d . . . . . C13 C 0.79783(18) 0.7095(2) 0.31670(15) 0.0257(7) Uani 1 1 d . . . . . C14 C 0.8681(2) 0.7257(2) 0.31104(16) 0.0305(8) Uani 1 1 d . . . . . H14 H 0.892949 0.786326 0.322992 0.037 Uiso 1 1 calc R U . . . C15 C 0.9022(2) 0.6541(3) 0.28810(17) 0.0334(8) Uani 1 1 d . . . . . H15 H 0.949941 0.666617 0.284188 0.040 Uiso 1 1 calc R U . . . C16 C 0.8680(2) 0.5652(3) 0.27086(16) 0.0307(8) Uani 1 1 d . . . . . H16 H 0.892335 0.517261 0.255094 0.037 Uiso 1 1 calc R U . . . C17 C 0.79760(19) 0.5447(2) 0.27637(15) 0.0270(7) Uani 1 1 d . . . . . C18 C 0.7627(2) 0.4446(2) 0.26154(17) 0.0315(8) Uani 1 1 d . . . . . H18 H 0.706487 0.450151 0.252942 0.038 Uiso 1 1 calc R U . . . C19 C 0.7992(3) 0.3777(3) 0.3191(2) 0.0527(12) Uani 1 1 d . . . . . H19A H 0.775634 0.313664 0.308735 0.079 Uiso 1 1 calc R U . . . H19B H 0.790458 0.403866 0.355987 0.079 Uiso 1 1 calc R U . . . H19C H 0.854761 0.372641 0.329394 0.079 Uiso 1 1 calc R U . . . C20 C 0.7704(2) 0.4008(3) 0.2022(2) 0.0431(10) Uani 1 1 d . . . . . H20A H 0.744541 0.337991 0.193156 0.065 Uiso 1 1 calc R U . . . H20B H 0.825104 0.392496 0.209996 0.065 Uiso 1 1 calc R U . . . H20C H 0.746359 0.443714 0.165584 0.065 Uiso 1 1 calc R U . . . C21 C 0.7584(2) 0.7899(2) 0.33838(17) 0.0329(8) Uani 1 1 d . . . . . H21 H 0.727293 0.759083 0.360603 0.039 Uiso 1 1 calc R U . . . C22 C 0.8143(3) 0.8595(3) 0.3855(2) 0.0545(12) Uani 1 1 d . . . . . H22A H 0.841262 0.896864 0.363641 0.082 Uiso 1 1 calc R U . . . H22B H 0.852065 0.823123 0.420796 0.082 Uiso 1 1 calc R U . . . H22C H 0.785766 0.903242 0.402416 0.082 Uiso 1 1 calc R U . . . C23 C 0.7028(3) 0.8449(3) 0.2816(2) 0.0567(13) Uani 1 1 d . . . . . H23A H 0.731706 0.878480 0.259761 0.085 Uiso 1 1 calc R U . . . H23B H 0.674383 0.891942 0.296393 0.085 Uiso 1 1 calc R U . . . H23C H 0.666342 0.799775 0.251814 0.085 Uiso 1 1 calc R U . . . C24 C 0.52948(18) 0.5814(2) 0.36260(15) 0.0225(7) Uani 1 1 d . . . . . C25 C 0.52057(19) 0.4897(2) 0.38578(15) 0.0270(7) Uani 1 1 d . . . . . C26 C 0.4685(2) 0.4809(3) 0.41448(17) 0.0343(8) Uani 1 1 d . . . . . H26 H 0.461751 0.420099 0.430888 0.041 Uiso 1 1 calc R U . . . C27 C 0.4255(2) 0.5593(3) 0.42003(18) 0.0372(8) Uani 1 1 d . . . . . H27 H 0.390420 0.551955 0.440827 0.045 Uiso 1 1 calc R U . . . C28 C 0.4336(2) 0.6488(3) 0.39521(17) 0.0348(8) Uani 1 1 d . . . . . H28 H 0.402728 0.701425 0.398189 0.042 Uiso 1 1 calc R U . . . C29 C 0.48617(18) 0.6621(2) 0.36618(15) 0.0257(7) Uani 1 1 d . . . . . C30 C 0.5639(2) 0.4027(2) 0.37593(18) 0.0318(8) Uani 1 1 d . . . . . H30 H 0.600294 0.425678 0.356220 0.038 Uiso 1 1 calc R U . . . C31 C 0.6117(3) 0.3527(3) 0.43916(19) 0.0526(12) Uani 1 1 d . . . . . H31A H 0.638443 0.297096 0.430652 0.079 Uiso 1 1 calc R U . . . H31B H 0.577431 0.331074 0.460108 0.079 Uiso 1 1 calc R U . . . H31C H 0.649637 0.398118 0.467170 0.079 Uiso 1 1 calc R U . . . C32 C 0.5077(3) 0.3324(3) 0.32937(19) 0.0460(10) Uani 1 1 d . . . . . H32A H 0.477554 0.366077 0.289530 0.069 Uiso 1 1 calc R U . . . H32B H 0.472780 0.306449 0.348431 0.069 Uiso 1 1 calc R U . . . H32C H 0.536507 0.279526 0.320216 0.069 Uiso 1 1 calc R U . . . C33 C 0.4964(2) 0.7593(2) 0.33921(16) 0.0296(8) Uani 1 1 d . . . . . H33 H 0.516230 0.746764 0.304730 0.036 Uiso 1 1 calc R U . . . C34 C 0.5556(2) 0.8215(3) 0.38958(19) 0.0439(10) Uani 1 1 d . . . . . H34A H 0.605946 0.789543 0.404628 0.066 Uiso 1 1 calc R U . . . H34B H 0.539606 0.831077 0.425651 0.066 Uiso 1 1 calc R U . . . H34C H 0.559260 0.884116 0.370929 0.066 Uiso 1 1 calc R U . . . C35 C 0.4208(2) 0.8150(3) 0.3092(2) 0.0534(12) Uani 1 1 d . . . . . H35A H 0.429408 0.872587 0.287764 0.080 Uiso 1 1 calc R U . . . H35B H 0.402608 0.834174 0.342701 0.080 Uiso 1 1 calc R U . . . H35C H 0.382027 0.774011 0.277936 0.080 Uiso 1 1 calc R U . . . C36 C 0.62143(19) 0.5962(2) 0.24888(15) 0.0237(7) Uani 1 1 d . . . . . C37 C 0.59591(19) 0.5967(2) 0.17944(15) 0.0243(7) Uani 1 1 d . . . . . C38 C 0.6279(2) 0.6059(2) 0.13432(17) 0.0304(8) Uani 1 1 d . . . . . H38 H 0.682069 0.612401 0.146490 0.037 Uiso 1 1 calc R U . . . C39 C 0.5768(2) 0.6055(3) 0.06823(17) 0.0365(9) Uani 1 1 d . . . . . H39 H 0.598680 0.610595 0.036812 0.044 Uiso 1 1 calc R U . . . C40 C 0.4987(2) 0.5982(2) 0.04804(17) 0.0354(9) Uani 1 1 d . . . . . H40 H 0.467404 0.599510 0.003642 0.042 Uiso 1 1 calc R U . . . C41 C 0.4641(2) 0.5886(2) 0.09416(17) 0.0296(8) Uani 1 1 d . . . . . C42 C 0.5137(2) 0.5883(2) 0.15798(16) 0.0257(7) Uani 1 1 d . . . . . C43 C 0.48842(19) 0.5832(2) 0.20968(16) 0.0248(7) Uani 1 1 d . . . . . C44 C 0.4107(2) 0.5770(2) 0.19660(18) 0.0307(8) Uani 1 1 d . . . . . H44 H 0.392043 0.573517 0.230068 0.037 Uiso 1 1 calc R U . . . C45 C 0.3593(2) 0.5760(2) 0.13141(18) 0.0349(9) Uani 1 1 d . . . . . H45 H 0.305524 0.571322 0.121752 0.042 Uiso 1 1 calc R U . . . C46 C 0.3842(2) 0.5816(2) 0.08175(18) 0.0345(9) Uani 1 1 d . . . . . H46 H 0.347628 0.580787 0.038856 0.041 Uiso 1 1 calc R U . . . C47 C 0.56006(18) 0.5891(2) 0.26628(16) 0.0235(7) Uani 1 1 d . . . . . C48 C 0.9633(3) 1.1433(3) 0.5182(2) 0.0520(11) Uani 1 1 d . . . . . H48A H 0.962677 1.139769 0.561737 0.062 Uiso 1 1 calc R U . . . H48B H 1.015835 1.126314 0.521288 0.062 Uiso 1 1 calc R U . . . C49 C 0.8984(3) 0.3830(3) 0.8110(2) 0.0484(10) Uani 1 1 d . . . . . H49A H 0.910988 0.361264 0.855535 0.058 Uiso 1 1 calc R U . . . H49B H 0.926326 0.443954 0.812481 0.058 Uiso 1 1 calc R U . . . C50 C 0.8296(3) 0.2661(3) 0.6003(2) 0.0584(12) Uani 1 1 d . . . . . H50A H 0.874886 0.284081 0.590474 0.070 Uiso 1 1 calc R U . . . H50B H 0.848847 0.235197 0.643008 0.070 Uiso 1 1 calc R U . . . C51 C 0.8498(2) -0.0770(3) 0.5858(2) 0.0469(10) Uani 1 1 d . . . . . H51A H 0.869700 -0.012621 0.580974 0.056 Uiso 1 1 calc R U . . . H51B H 0.851564 -0.082134 0.630002 0.056 Uiso 1 1 calc R U . . . C8A C 0.9595(4) 0.4994(8) 0.5892(3) 0.038(3) Uani 0.584(18) 1 d . . P C 1 H8A1 H 1.015897 0.493230 0.601372 0.046 Uiso 0.584(18) 1 calc R U P C 1 H8A2 H 0.938826 0.434113 0.590319 0.046 Uiso 0.584(18) 1 calc R U P C 1 C8 C 0.9752(6) 0.5658(12) 0.5917(4) 0.039(4) Uani 0.416(18) 1 d . . P C 2 H8A H 1.022552 0.526022 0.606023 0.046 Uiso 0.416(18) 1 calc R U P C 2 H8B H 0.991217 0.633285 0.589797 0.046 Uiso 0.416(18) 1 calc R U P C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br01 0.0295(2) 0.0337(2) 0.0298(2) -0.00056(14) 0.00786(15) -0.00394(14) Cl1 0.1611(17) 0.0365(6) 0.1368(14) 0.0073(7) 0.0979(14) -0.0091(8) N1 0.0258(15) 0.0367(16) 0.0255(16) -0.0010(12) 0.0043(12) 0.0076(12) C1 0.036(2) 0.049(2) 0.0244(18) -0.0048(16) 0.0075(16) 0.0105(17) B1 0.0189(17) 0.0219(17) 0.0257(19) 0.0001(14) 0.0085(15) 0.0005(14) Cl2 0.0810(9) 0.0503(6) 0.0476(7) -0.0039(5) 0.0195(6) -0.0165(6) N2 0.0193(13) 0.0262(14) 0.0235(14) 0.0005(10) 0.0081(11) 0.0011(11) C2 0.0338(19) 0.0358(18) 0.0293(18) -0.0037(15) 0.0136(15) 0.0027(16) Cl3 0.0563(7) 0.0452(6) 0.0745(8) 0.0009(5) 0.0309(6) 0.0060(5) N3 0.0192(13) 0.0242(13) 0.0216(14) -0.0016(10) 0.0061(11) -0.0001(11) C3 0.0284(18) 0.0391(19) 0.0258(18) -0.0037(14) 0.0106(14) -0.0006(15) Cl4 0.0419(5) 0.0483(5) 0.0411(5) -0.0092(4) 0.0177(4) -0.0057(4) N4 0.0211(14) 0.0222(13) 0.0240(14) 0.0015(10) 0.0091(11) 0.0006(10) C4 0.0226(16) 0.0225(15) 0.0247(17) 0.0021(12) 0.0079(13) 0.0002(13) C5 0.0248(17) 0.0241(16) 0.0245(17) -0.0012(12) 0.0080(14) -0.0010(13) Cl5 0.0957(11) 0.0520(7) 0.0715(9) -0.0112(6) -0.0152(8) -0.0030(7) C6 0.0228(17) 0.0342(17) 0.0254(18) -0.0022(14) 0.0069(14) 0.0032(14) Cl6 0.0686(8) 0.0547(7) 0.0779(9) -0.0137(6) -0.0043(7) 0.0228(6) C7 0.0261(19) 0.065(3) 0.031(2) -0.0084(18) 0.0041(16) 0.0107(18) Cl8 0.0405(5) 0.0480(6) 0.0526(6) 0.0088(4) 0.0136(5) 0.0013(4) Cl7 0.0410(6) 0.0488(6) 0.0554(7) 0.0099(5) 0.0114(5) 0.0006(4) C9 0.029(2) 0.071(3) 0.034(2) -0.0046(19) 0.0026(17) 0.020(2) C10 0.0236(17) 0.0296(16) 0.0274(18) 0.0011(13) 0.0085(14) 0.0056(14) C11 0.0204(16) 0.0247(15) 0.0284(18) 0.0013(13) 0.0080(14) -0.0011(13) C12 0.0214(16) 0.0267(16) 0.0200(16) 0.0031(12) 0.0060(13) 0.0002(13) C13 0.0254(17) 0.0285(16) 0.0211(16) 0.0004(13) 0.0065(13) -0.0017(13) C14 0.0285(18) 0.0328(18) 0.0278(18) 0.0027(14) 0.0082(15) -0.0073(15) C15 0.0240(17) 0.041(2) 0.035(2) 0.0092(16) 0.0112(15) -0.0018(15) C16 0.0256(18) 0.0384(18) 0.0302(19) 0.0082(15) 0.0130(15) 0.0079(15) C17 0.0247(17) 0.0291(17) 0.0237(17) 0.0016(13) 0.0054(14) 0.0004(14) C18 0.0254(18) 0.0279(17) 0.041(2) -0.0020(15) 0.0125(16) 0.0004(14) C19 0.077(3) 0.033(2) 0.049(3) -0.0036(18) 0.026(2) -0.006(2) C20 0.042(2) 0.040(2) 0.044(2) -0.0114(17) 0.0134(19) -0.0017(17) C21 0.037(2) 0.0292(18) 0.038(2) -0.0057(15) 0.0211(17) -0.0082(15) C22 0.062(3) 0.049(2) 0.047(3) -0.015(2) 0.015(2) -0.001(2) C23 0.049(3) 0.045(2) 0.060(3) -0.016(2) 0.003(2) 0.018(2) C24 0.0188(15) 0.0219(15) 0.0247(17) -0.0016(12) 0.0060(13) -0.0015(12) C25 0.0278(17) 0.0238(16) 0.0275(18) -0.0003(13) 0.0082(14) -0.0025(14) C26 0.0322(19) 0.0322(18) 0.040(2) 0.0043(15) 0.0149(16) -0.0054(15) C27 0.0305(19) 0.047(2) 0.040(2) -0.0006(17) 0.0201(17) -0.0032(17) C28 0.0265(18) 0.039(2) 0.039(2) -0.0037(16) 0.0129(16) 0.0025(15) C29 0.0235(17) 0.0248(16) 0.0264(17) 0.0001(13) 0.0070(14) 0.0012(13) C30 0.037(2) 0.0200(16) 0.041(2) 0.0025(14) 0.0179(17) -0.0029(14) C31 0.063(3) 0.039(2) 0.046(2) -0.0001(18) 0.008(2) 0.019(2) C32 0.055(3) 0.035(2) 0.044(2) -0.0061(17) 0.014(2) -0.0005(18) C33 0.0307(18) 0.0262(17) 0.0324(19) 0.0009(14) 0.0124(15) 0.0068(14) C34 0.047(2) 0.0280(18) 0.046(2) 0.0039(16) 0.0055(19) -0.0045(17) C35 0.042(2) 0.036(2) 0.068(3) 0.010(2) 0.005(2) 0.0110(18) C36 0.0234(17) 0.0185(15) 0.0256(17) -0.0002(12) 0.0053(13) 0.0000(12) C37 0.0273(17) 0.0178(15) 0.0235(17) -0.0015(12) 0.0048(14) -0.0008(12) C38 0.0313(19) 0.0274(17) 0.0303(19) -0.0017(14) 0.0092(15) 0.0004(14) C39 0.044(2) 0.039(2) 0.0252(19) -0.0019(15) 0.0118(16) 0.0038(17) C40 0.040(2) 0.0342(19) 0.0251(19) -0.0028(14) 0.0043(16) 0.0032(16) C41 0.0303(18) 0.0194(15) 0.0308(19) -0.0034(13) 0.0024(15) 0.0012(13) C42 0.0264(17) 0.0199(15) 0.0280(18) -0.0022(12) 0.0075(14) -0.0007(13) C43 0.0250(17) 0.0167(15) 0.0286(18) 0.0013(12) 0.0058(14) -0.0003(12) C44 0.0271(18) 0.0222(16) 0.037(2) 0.0040(14) 0.0064(15) -0.0003(14) C45 0.0234(18) 0.0268(17) 0.045(2) -0.0018(15) 0.0021(16) -0.0043(14) C46 0.0292(19) 0.0270(18) 0.034(2) 0.0019(14) -0.0027(16) -0.0034(14) C47 0.0206(16) 0.0192(15) 0.0275(18) -0.0005(12) 0.0057(13) 0.0001(12) C48 0.066(3) 0.045(2) 0.048(3) -0.0072(19) 0.024(2) -0.015(2) C49 0.050(3) 0.049(2) 0.048(3) -0.0166(19) 0.020(2) -0.011(2) C50 0.057(3) 0.042(2) 0.061(3) -0.004(2) 0.005(2) -0.004(2) C51 0.046(2) 0.041(2) 0.050(3) -0.0057(18) 0.015(2) -0.0138(18) C8A 0.026(3) 0.052(6) 0.031(4) 0.000(3) 0.005(3) 0.015(4) C8 0.025(5) 0.053(9) 0.025(5) -0.004(5) -0.004(4) 0.017(5) 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' B B 0.0013 0.0007 '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' Cl Cl 0.1484 0.1585 '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' 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 C5 N1 C1 122.4(3) . . ? C5 N1 C9 122.2(3) . . ? C1 N1 C9 115.4(3) . . ? N1 C1 C2 111.4(3) . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? N4 B1 N3 108.1(3) . . ? N4 B1 N2 125.3(3) . . ? N3 B1 N2 126.6(3) . . ? C10 N2 C11 116.8(3) . . ? C10 N2 B1 120.9(3) . . ? C11 N2 B1 122.3(3) . . ? C1 C2 C3 110.7(3) . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C36 N3 B1 105.6(3) . . ? C36 N3 C12 121.4(3) . . ? B1 N3 C12 132.5(3) . . ? C2 C3 C4 108.9(3) . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C47 N4 C24 120.8(3) . . ? C47 N4 B1 105.6(3) . . ? C24 N4 B1 133.3(3) . . ? C11 C4 C5 119.6(3) . . ? C11 C4 C3 120.9(3) . . ? C5 C4 C3 119.5(3) . . ? N1 C5 C4 121.4(3) . . ? N1 C5 C6 120.9(3) . . ? C4 C5 C6 117.7(3) . . ? C10 C6 C5 118.9(3) . . ? C10 C6 C7 120.8(3) . . ? C5 C6 C7 120.4(3) . . ? C8A C7 C6 111.9(4) . . ? C6 C7 C8 110.3(5) . . ? C8A C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8A C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C8 C9 N1 113.4(5) . . ? N1 C9 C8A 113.2(4) . . ? N1 C9 H9A 108.9 . . ? C8A C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? C8A C9 H9B 108.9 . . ? H9A C9 H9B 107.8 . . ? C6 C10 N2 124.0(3) . . ? C6 C10 H10 118.0 . . ? N2 C10 H10 118.0 . . ? C4 C11 N2 123.1(3) . . ? C4 C11 H11 118.4 . . ? N2 C11 H11 118.4 . . ? C17 C12 C13 122.2(3) . . ? C17 C12 N3 119.3(3) . . ? C13 C12 N3 118.5(3) . . ? C14 C13 C12 117.9(3) . . ? C14 C13 C21 120.4(3) . . ? C12 C13 C21 121.6(3) . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 121.2(3) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 117.6(3) . . ? C16 C17 C18 120.4(3) . . ? C12 C17 C18 121.9(3) . . ? C17 C18 C20 112.4(3) . . ? C17 C18 C19 110.7(3) . . ? C20 C18 C19 110.1(3) . . ? C17 C18 H18 107.8 . . ? C20 C18 H18 107.8 . . ? C19 C18 H18 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C23 C21 C13 111.0(3) . . ? C23 C21 C22 109.9(3) . . ? C13 C21 C22 113.7(3) . . ? C23 C21 H21 107.3 . . ? C13 C21 H21 107.3 . . ? C22 C21 H21 107.3 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C29 C24 C25 123.0(3) . . ? C29 C24 N4 118.6(3) . . ? C25 C24 N4 118.4(3) . . ? C26 C25 C24 117.7(3) . . ? C26 C25 C30 121.2(3) . . ? C24 C25 C30 121.1(3) . . ? C25 C26 C27 121.2(3) . . ? C25 C26 H26 119.4 . . ? C27 C26 H26 119.4 . . ? C26 C27 C28 120.3(3) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C29 C28 C27 120.9(3) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 C24 116.8(3) . . ? C28 C29 C33 121.9(3) . . ? C24 C29 C33 121.3(3) . . ? C25 C30 C32 110.0(3) . . ? C25 C30 C31 112.1(3) . . ? C32 C30 C31 111.0(3) . . ? C25 C30 H30 107.8 . . ? C32 C30 H30 107.8 . . ? C31 C30 H30 107.8 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C29 111.8(3) . . ? C34 C33 C35 109.4(3) . . ? C29 C33 C35 112.9(3) . . ? C34 C33 H33 107.5 . . ? C29 C33 H33 107.5 . . ? C35 C33 H33 107.5 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C47 C36 N3 109.9(3) . . ? C47 C36 C37 110.4(3) . . ? N3 C36 C37 139.7(3) . . ? C38 C37 C42 118.4(3) . . ? C38 C37 C36 138.2(3) . . ? C42 C37 C36 103.4(3) . . ? C37 C38 C39 117.8(3) . . ? C37 C38 H38 121.1 . . ? C39 C38 H38 121.1 . . ? C40 C39 C38 123.6(4) . . ? C40 C39 H39 118.2 . . ? C38 C39 H39 118.2 . . ? C39 C40 C41 119.5(3) . . ? C39 C40 H40 120.2 . . ? C41 C40 H40 120.2 . . ? C42 C41 C46 116.3(3) . . ? C42 C41 C40 116.6(3) . . ? C46 C41 C40 127.0(3) . . ? C41 C42 C43 123.7(3) . . ? C41 C42 C37 124.0(3) . . ? C43 C42 C37 112.3(3) . . ? C44 C43 C42 119.1(3) . . ? C44 C43 C47 137.4(3) . . ? C42 C43 C47 103.5(3) . . ? C43 C44 C45 117.8(4) . . ? C43 C44 H44 121.1 . . ? C45 C44 H44 121.1 . . ? C46 C45 C44 122.8(3) . . ? C46 C45 H45 118.6 . . ? C44 C45 H45 118.6 . . ? C45 C46 C41 120.4(3) . . ? C45 C46 H46 119.8 . . ? C41 C46 H46 119.8 . . ? C36 C47 N4 110.6(3) . . ? C36 C47 C43 110.4(3) . . ? N4 C47 C43 139.0(3) . . ? Cl1 C48 Cl2 111.2(3) . . ? Cl1 C48 H48A 109.4 . . ? Cl2 C48 H48A 109.4 . . ? Cl1 C48 H48B 109.4 . . ? Cl2 C48 H48B 109.4 . . ? H48A C48 H48B 108.0 . . ? Cl3 C49 Cl4 111.6(2) . . ? Cl3 C49 H49A 109.3 . . ? Cl4 C49 H49A 109.3 . . ? Cl3 C49 H49B 109.3 . . ? Cl4 C49 H49B 109.3 . . ? H49A C49 H49B 108.0 . . ? Cl5 C50 Cl6 113.4(3) . . ? Cl5 C50 H50A 108.9 . . ? Cl6 C50 H50A 108.9 . . ? Cl5 C50 H50B 108.9 . . ? Cl6 C50 H50B 108.9 . . ? H50A C50 H50B 107.7 . . ? Cl8 C51 Cl7 111.0(2) . . ? Cl8 C51 H51A 109.4 . . ? Cl7 C51 H51A 109.4 . . ? Cl8 C51 H51B 109.4 . . ? Cl7 C51 H51B 109.4 . . ? H51A C51 H51B 108.0 . . ? C7 C8A C9 115.2(6) . . ? C7 C8A H8A1 108.5 . . ? C9 C8A H8A1 108.5 . . ? C7 C8A H8A2 108.5 . . ? C9 C8A H8A2 108.5 . . ? H8A1 C8A H8A2 107.5 . . ? C9 C8 C7 119.4(9) . . ? C9 C8 H8A 107.5 . . ? C7 C8 H8A 107.5 . . ? C9 C8 H8B 107.5 . . ? C7 C8 H8B 107.5 . . ? H8A C8 H8B 107.0 . . ? 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 Cl1 C48 1.753(5) . ? N1 C5 1.331(4) . ? N1 C1 1.468(5) . ? N1 C9 1.475(5) . ? C1 C2 1.502(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? B1 N4 1.434(4) . ? B1 N3 1.437(5) . ? B1 N2 1.486(4) . ? Cl2 C48 1.758(4) . ? N2 C10 1.369(4) . ? N2 C11 1.380(4) . ? C2 C3 1.515(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? Cl3 C49 1.768(5) . ? N3 C36 1.402(4) . ? N3 C12 1.440(4) . ? C3 C4 1.518(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? Cl4 C49 1.770(4) . ? N4 C47 1.394(4) . ? N4 C24 1.434(4) . ? C4 C11 1.365(4) . ? C4 C5 1.411(5) . ? C5 C6 1.433(5) . ? Cl5 C50 1.720(4) . ? C6 C10 1.357(5) . ? C6 C7 1.498(5) . ? Cl6 C50 1.729(5) . ? C7 C8A 1.451(8) . ? C7 C8 1.516(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? Cl8 C51 1.757(5) . ? Cl7 C51 1.767(4) . ? C9 C8 1.377(11) . ? C9 C8A 1.508(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C17 1.404(5) . ? C12 C13 1.408(4) . ? C13 C14 1.391(5) . ? C13 C21 1.521(5) . ? C14 C15 1.385(5) . ? C14 H14 0.9500 . ? C15 C16 1.377(5) . ? C15 H15 0.9500 . ? C16 C17 1.402(5) . ? C16 H16 0.9500 . ? C17 C18 1.517(5) . ? C18 C20 1.529(5) . ? C18 C19 1.532(6) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C23 1.515(6) . ? C21 C22 1.522(5) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C29 1.405(4) . ? C24 C25 1.411(4) . ? C25 C26 1.369(5) . ? C25 C30 1.520(5) . ? C26 C27 1.389(5) . ? C26 H26 0.9500 . ? C27 C28 1.396(5) . ? C27 H27 0.9500 . ? C28 C29 1.391(5) . ? C28 H28 0.9500 . ? C29 C33 1.522(5) . ? C30 C32 1.524(5) . ? C30 C31 1.532(5) . ? C30 H30 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.520(5) . ? C33 C35 1.527(5) . ? C33 H33 1.0000 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C47 1.355(5) . ? C36 C37 1.457(5) . ? C37 C38 1.374(5) . ? C37 C42 1.434(5) . ? C38 C39 1.434(5) . ? C38 H38 0.9500 . ? C39 C40 1.361(6) . ? C39 H39 0.9500 . ? C40 C41 1.431(6) . ? C40 H40 0.9500 . ? C41 C42 1.386(5) . ? C41 C46 1.419(5) . ? C42 C43 1.422(5) . ? C43 C44 1.374(5) . ? C43 C47 1.461(4) . ? C44 C45 1.420(5) . ? C44 H44 0.9500 . ? C45 C46 1.373(6) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? 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 C5 N1 C1 C2 -23.6(5) . . . . ? C9 N1 C1 C2 157.1(3) . . . . ? N4 B1 N2 C10 157.3(3) . . . . ? N3 B1 N2 C10 -20.8(5) . . . . ? N4 B1 N2 C11 -23.1(5) . . . . ? N3 B1 N2 C11 158.8(3) . . . . ? N1 C1 C2 C3 53.1(4) . . . . ? N4 B1 N3 C36 -0.6(3) . . . . ? N2 B1 N3 C36 177.7(3) . . . . ? N4 B1 N3 C12 171.5(3) . . . . ? N2 B1 N3 C12 -10.2(5) . . . . ? C1 C2 C3 C4 -54.9(4) . . . . ? N3 B1 N4 C47 1.7(3) . . . . ? N2 B1 N4 C47 -176.7(3) . . . . ? N3 B1 N4 C24 175.9(3) . . . . ? N2 B1 N4 C24 -2.5(5) . . . . ? C2 C3 C4 C11 -150.2(3) . . . . ? C2 C3 C4 C5 29.2(4) . . . . ? C1 N1 C5 C4 -3.5(5) . . . . ? C9 N1 C5 C4 175.6(3) . . . . ? C1 N1 C5 C6 177.2(3) . . . . ? C9 N1 C5 C6 -3.6(5) . . . . ? C11 C4 C5 N1 179.6(3) . . . . ? C3 C4 C5 N1 0.2(5) . . . . ? C11 C4 C5 C6 -1.1(5) . . . . ? C3 C4 C5 C6 179.4(3) . . . . ? N1 C5 C6 C10 -179.5(3) . . . . ? C4 C5 C6 C10 1.2(5) . . . . ? N1 C5 C6 C7 0.7(5) . . . . ? C4 C5 C6 C7 -178.6(3) . . . . ? C10 C6 C7 C8A -155.8(6) . . . . ? C5 C6 C7 C8A 24.0(7) . . . . ? C10 C6 C7 C8 163.6(8) . . . . ? C5 C6 C7 C8 -16.6(8) . . . . ? C5 N1 C9 C8 24.5(9) . . . . ? C1 N1 C9 C8 -156.3(8) . . . . ? C5 N1 C9 C8A -17.7(7) . . . . ? C1 N1 C9 C8A 161.5(6) . . . . ? C5 C6 C10 N2 -1.1(5) . . . . ? C7 C6 C10 N2 178.7(3) . . . . ? C11 N2 C10 C6 0.7(5) . . . . ? B1 N2 C10 C6 -179.7(3) . . . . ? C5 C4 C11 N2 0.8(5) . . . . ? C3 C4 C11 N2 -179.8(3) . . . . ? C10 N2 C11 C4 -0.6(4) . . . . ? B1 N2 C11 C4 179.8(3) . . . . ? C36 N3 C12 C17 -73.1(4) . . . . ? B1 N3 C12 C17 115.9(4) . . . . ? C36 N3 C12 C13 106.7(3) . . . . ? B1 N3 C12 C13 -64.4(4) . . . . ? C17 C12 C13 C14 0.6(5) . . . . ? N3 C12 C13 C14 -179.1(3) . . . . ? C17 C12 C13 C21 177.5(3) . . . . ? N3 C12 C13 C21 -2.2(4) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C21 C13 C14 C15 -176.6(3) . . . . ? C13 C14 C15 C16 -0.5(5) . . . . ? C14 C15 C16 C17 -0.2(5) . . . . ? C15 C16 C17 C12 1.2(5) . . . . ? C15 C16 C17 C18 -175.9(3) . . . . ? C13 C12 C17 C16 -1.4(5) . . . . ? N3 C12 C17 C16 178.3(3) . . . . ? C13 C12 C17 C18 175.7(3) . . . . ? N3 C12 C17 C18 -4.6(5) . . . . ? C16 C17 C18 C20 -41.3(4) . . . . ? C12 C17 C18 C20 141.7(3) . . . . ? C16 C17 C18 C19 82.2(4) . . . . ? C12 C17 C18 C19 -94.8(4) . . . . ? C14 C13 C21 C23 92.0(4) . . . . ? C12 C13 C21 C23 -84.9(4) . . . . ? C14 C13 C21 C22 -32.5(5) . . . . ? C12 C13 C21 C22 150.6(3) . . . . ? C47 N4 C24 C29 -81.3(4) . . . . ? B1 N4 C24 C29 105.3(4) . . . . ? C47 N4 C24 C25 97.3(3) . . . . ? B1 N4 C24 C25 -76.2(4) . . . . ? C29 C24 C25 C26 -1.8(5) . . . . ? N4 C24 C25 C26 179.7(3) . . . . ? C29 C24 C25 C30 174.9(3) . . . . ? N4 C24 C25 C30 -3.6(5) . . . . ? C24 C25 C26 C27 0.6(5) . . . . ? C30 C25 C26 C27 -176.1(3) . . . . ? C25 C26 C27 C28 1.2(6) . . . . ? C26 C27 C28 C29 -1.9(5) . . . . ? C27 C28 C29 C24 0.7(5) . . . . ? C27 C28 C29 C33 -179.5(3) . . . . ? C25 C24 C29 C28 1.1(5) . . . . ? N4 C24 C29 C28 179.6(3) . . . . ? C25 C24 C29 C33 -178.6(3) . . . . ? N4 C24 C29 C33 -0.1(4) . . . . ? C26 C25 C30 C32 65.2(4) . . . . ? C24 C25 C30 C32 -111.3(4) . . . . ? C26 C25 C30 C31 -58.8(5) . . . . ? C24 C25 C30 C31 124.6(4) . . . . ? C28 C29 C33 C34 88.0(4) . . . . ? C24 C29 C33 C34 -92.3(4) . . . . ? C28 C29 C33 C35 -35.9(5) . . . . ? C24 C29 C33 C35 143.8(3) . . . . ? B1 N3 C36 C47 -0.7(3) . . . . ? C12 N3 C36 C47 -173.9(3) . . . . ? B1 N3 C36 C37 179.0(4) . . . . ? C12 N3 C36 C37 5.8(5) . . . . ? C47 C36 C37 C38 176.6(4) . . . . ? N3 C36 C37 C38 -3.1(7) . . . . ? C47 C36 C37 C42 -0.5(3) . . . . ? N3 C36 C37 C42 179.8(3) . . . . ? C42 C37 C38 C39 -0.7(4) . . . . ? C36 C37 C38 C39 -177.5(3) . . . . ? C37 C38 C39 C40 1.2(5) . . . . ? C38 C39 C40 C41 -1.2(5) . . . . ? C39 C40 C41 C42 0.7(5) . . . . ? C39 C40 C41 C46 179.0(3) . . . . ? C46 C41 C42 C43 -1.1(4) . . . . ? C40 C41 C42 C43 177.4(3) . . . . ? C46 C41 C42 C37 -178.7(3) . . . . ? C40 C41 C42 C37 -0.2(5) . . . . ? C38 C37 C42 C41 0.2(5) . . . . ? C36 C37 C42 C41 178.1(3) . . . . ? C38 C37 C42 C43 -177.6(3) . . . . ? C36 C37 C42 C43 0.2(3) . . . . ? C41 C42 C43 C44 0.8(5) . . . . ? C37 C42 C43 C44 178.6(3) . . . . ? C41 C42 C43 C47 -177.7(3) . . . . ? C37 C42 C43 C47 0.1(3) . . . . ? C42 C43 C44 C45 0.0(4) . . . . ? C47 C43 C44 C45 177.9(3) . . . . ? C43 C44 C45 C46 -0.4(5) . . . . ? C44 C45 C46 C41 0.1(5) . . . . ? C42 C41 C46 C45 0.6(5) . . . . ? C40 C41 C46 C45 -177.7(3) . . . . ? N3 C36 C47 N4 1.9(3) . . . . ? C37 C36 C47 N4 -177.9(2) . . . . ? N3 C36 C47 C43 -179.6(2) . . . . ? C37 C36 C47 C43 0.6(3) . . . . ? C24 N4 C47 C36 -177.3(3) . . . . ? B1 N4 C47 C36 -2.2(3) . . . . ? C24 N4 C47 C43 4.9(5) . . . . ? B1 N4 C47 C43 179.9(3) . . . . ? C44 C43 C47 C36 -178.5(4) . . . . ? C42 C43 C47 C36 -0.4(3) . . . . ? C44 C43 C47 N4 -0.6(7) . . . . ? C42 C43 C47 N4 177.4(3) . . . . ? C6 C7 C8A C9 -45.3(9) . . . . ? N1 C9 C8A C7 43.1(9) . . . . ? N1 C9 C8 C7 -43.0(14) . . . . ? C6 C7 C8 C9 39.2(13) . . . . ?