#------------------------------------------------------------------------------ #$Date: 2020-07-06 04:53:51 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253799 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126525.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_7126525 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 'Br, 3(C H2 Cl2), C43 H50 B N4' _chemical_formula_sum 'C46 H56 B Br Cl6 N4' _chemical_formula_weight 968.427 _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 _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 80.556(4) _cell_angle_beta 77.491(4) _cell_angle_gamma 79.442(4) _cell_formula_units_Z 2 _cell_length_a 11.7554(14) _cell_length_b 13.4782(16) _cell_length_c 16.2117(19) _cell_measurement_reflns_used 9921 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.38 _cell_measurement_theta_min 2.41 _cell_volume 2444.4(5) _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 0.991 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0841 _diffrn_reflns_av_unetI/netI 0.0790 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 35523 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.458 _diffrn_reflns_theta_min 2.245 _exptl_absorpt_coefficient_mu 1.204 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.5643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1002 before and 0.0650 after correction. The Ratio of minimum to maximum transmission is 0.7570. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'clear light orange' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.316 _exptl_crystal_description block _exptl_crystal_F_000 1633 _refine_diff_density_max 0.718 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.099 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 533 _refine_ls_number_reflns 9941 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0570 _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^)+(0.0659P)^2^+4.5589P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1513 _refine_ls_wR_factor_ref 0.1671 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7074 _reflns_number_total 9941 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc01575j2.cif _cod_data_source_block 5 _cod_depositor_comments 'Adding full bibliography for 7126523--7126527.cif.' _cod_database_code 7126525 _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 2_a.res in P-1 2.res created by SHELXL-2016/6 at 21:14:29 on 27-Dec-2019 REM Old TITL 2 in P-1 REM SHELXT solution in P-1 REM R1 0.147, Rweak 0.024, Alpha 0.052, Orientation as input REM Formula found by SHELXT: C44 B3 N4 Cl6 Br CELL 0.71073 11.7554 13.4782 16.2117 80.556 77.491 79.442 ZERR 23 0.0014 0.0016 0.0019 0.004 0.004 0.004 LATT 1 SFAC C H B N Cl Br UNIT 23 23 23 23 23 23 L.S. 99 PLAN 20 TEMP -173.11 BOND $H list 4 fmap 2 53 acta REM REM REM WGHT 0.065900 4.558900 FVAR 0.38045 BR1 6 0.182769 0.639340 0.557287 11.00000 0.03466 0.03040 = 0.03277 -0.00227 -0.00987 -0.00833 N1 4 0.520593 0.137629 0.776069 11.00000 0.02680 0.02208 = 0.02230 -0.00431 -0.00664 -0.00557 B1 3 0.447401 0.234959 0.772086 11.00000 0.02528 0.02652 = 0.02009 -0.00522 -0.00245 -0.00440 CL1 5 0.220380 0.269015 0.460335 11.00000 0.04273 0.07502 = 0.04602 -0.02636 -0.00496 -0.00881 C1 1 0.892943 -0.034112 0.853338 11.00000 0.03352 0.03474 = 0.03255 -0.00590 -0.00584 0.00208 AFIX 43 H1 2 0.934480 -0.101173 0.849601 11.00000 -1.20000 AFIX 0 C2 1 0.941459 0.032721 0.886140 11.00000 0.02732 0.04015 = 0.03001 -0.00357 -0.00740 -0.00246 AFIX 43 H2 2 1.015196 0.011740 0.903662 11.00000 -1.20000 AFIX 0 CL2 5 0.159835 0.259905 0.296027 11.00000 0.04912 0.07351 = 0.04751 -0.01311 -0.01423 -0.00717 N2 4 0.498801 0.302339 0.807599 11.00000 0.02243 0.02413 = 0.02352 -0.00596 -0.00526 -0.00327 CL3 5 0.029068 -0.026181 0.616847 11.00000 0.05320 0.04772 = 0.05783 -0.00889 -0.01506 0.00282 N3 4 0.338248 0.258555 0.737474 11.00000 0.02755 0.02581 = 0.02664 -0.00501 -0.00648 -0.00779 C3 1 0.880885 0.133094 0.893677 11.00000 0.02725 0.03802 = 0.02168 -0.00377 -0.00312 -0.00728 C4 1 0.916747 0.211746 0.926993 11.00000 0.02404 0.04676 = 0.02805 -0.00587 -0.00628 -0.00919 AFIX 43 H4 2 0.988737 0.199294 0.947254 11.00000 -1.20000 AFIX 0 CL4 5 0.225315 -0.097314 0.705060 11.00000 0.05269 0.09698 = 0.09230 -0.03559 -0.03246 -0.01310 N4 4 0.027881 0.325773 0.642650 11.00000 0.02567 0.02987 = 0.02972 -0.00271 -0.00747 -0.00640 CL5 5 0.994249 0.494440 0.820433 11.00000 0.05241 0.05434 = 0.05982 -0.00524 0.00478 -0.01204 C5 1 0.847380 0.304991 0.929704 11.00000 0.03608 0.04170 = 0.03168 -0.01048 -0.00806 -0.01598 AFIX 43 H5 2 0.872778 0.355817 0.952594 11.00000 -1.20000 AFIX 0 C6 1 0.739565 0.329334 0.900024 11.00000 0.02859 0.03322 = 0.02842 -0.00835 -0.00367 -0.00689 AFIX 43 H6 2 0.693739 0.394935 0.903003 11.00000 -1.20000 AFIX 0 CL6 5 1.054792 0.678517 0.861605 11.00000 0.05978 0.05120 = 0.03923 -0.01202 -0.01091 0.00745 C7 1 0.702970 0.256495 0.867059 11.00000 0.02785 0.02992 = 0.01920 -0.00374 -0.00238 -0.00852 C8 1 0.775056 0.158493 0.865079 11.00000 0.02457 0.03200 = 0.01847 -0.00345 -0.00372 -0.00756 C9 1 0.724537 0.089201 0.830504 11.00000 0.02667 0.02872 = 0.01805 -0.00168 -0.00379 -0.00485 C10 1 0.784660 -0.008047 0.824994 11.00000 0.03242 0.02943 = 0.02860 -0.00586 -0.00635 -0.00429 AFIX 43 H10 2 0.754039 -0.056303 0.802700 11.00000 -1.20000 AFIX 0 C11 1 0.615763 0.149529 0.810222 11.00000 0.02918 0.02713 = 0.01956 -0.00297 -0.00474 -0.00836 C12 1 0.602517 0.246365 0.829388 11.00000 0.02225 0.02876 = 0.02146 -0.00516 -0.00219 -0.00518 C13 1 0.520471 0.045327 0.741241 11.00000 0.02597 0.02354 = 0.02423 -0.00520 -0.00880 -0.00462 C14 1 0.475642 -0.036219 0.795209 11.00000 0.02637 0.02812 = 0.02640 -0.00527 -0.00770 -0.00495 C15 1 0.483867 -0.126413 0.760646 11.00000 0.03143 0.02574 = 0.03029 -0.00029 -0.00667 -0.00842 AFIX 43 H15 2 0.455554 -0.183765 0.795955 11.00000 -1.20000 AFIX 0 C17 1 0.574968 -0.050415 0.623014 11.00000 0.03176 0.03725 = 0.02267 -0.01133 -0.00273 -0.00993 AFIX 43 H17 2 0.607849 -0.056285 0.564769 11.00000 -1.20000 AFIX 0 C16 1 0.532615 -0.133079 0.675873 11.00000 0.03497 0.02808 = 0.03419 -0.01111 -0.00531 -0.00832 AFIX 43 H16 2 0.537238 -0.194859 0.653458 11.00000 -1.20000 AFIX 0 C18 1 0.569907 0.041506 0.654337 11.00000 0.02152 0.03250 = 0.02731 -0.00660 -0.00681 -0.00432 C19 1 0.621836 0.129893 0.597531 11.00000 0.03291 0.03032 = 0.02373 -0.00191 -0.00491 -0.00819 AFIX 13 H19 2 0.605517 0.188083 0.631692 11.00000 -1.20000 AFIX 0 C20 1 0.565502 0.165712 0.519032 11.00000 0.05303 0.05656 = 0.05046 0.01721 -0.02591 -0.02406 AFIX 137 H20A 2 0.597703 0.225845 0.486859 11.00000 -1.50000 H20B 2 0.479952 0.183072 0.537050 11.00000 -1.50000 H20C 2 0.582742 0.111178 0.482868 11.00000 -1.50000 AFIX 0 C21 1 0.754794 0.102095 0.573272 11.00000 0.03306 0.04858 = 0.06163 0.01316 -0.00550 -0.01310 AFIX 137 H21A 2 0.788181 0.160824 0.539363 11.00000 -1.50000 H21B 2 0.773816 0.044941 0.539748 11.00000 -1.50000 H21C 2 0.788199 0.082577 0.625046 11.00000 -1.50000 AFIX 0 C22 1 0.418379 -0.029171 0.888391 11.00000 0.03602 0.02952 = 0.02604 -0.00356 -0.00379 -0.00751 AFIX 13 H22 2 0.416614 0.041767 0.899992 11.00000 -1.20000 AFIX 0 C23 1 0.291100 -0.051754 0.908610 11.00000 0.03399 0.04436 = 0.02817 0.00172 -0.00113 -0.00543 AFIX 137 H23A 2 0.254673 -0.039242 0.967077 11.00000 -1.50000 H23B 2 0.291490 -0.123058 0.902802 11.00000 -1.50000 H23C 2 0.245952 -0.007367 0.868848 11.00000 -1.50000 AFIX 0 C24 1 0.489028 -0.101928 0.947669 11.00000 0.04098 0.04251 = 0.02684 -0.00142 -0.00874 -0.00819 AFIX 137 H24A 2 0.450986 -0.095149 1.006977 11.00000 -1.50000 H24B 2 0.569187 -0.085547 0.937313 11.00000 -1.50000 H24C 2 0.492438 -0.171972 0.936913 11.00000 -1.50000 AFIX 0 C25 1 0.454571 0.406354 0.825316 11.00000 0.02492 0.02605 = 0.03128 -0.00871 -0.00879 -0.00385 C26 1 0.486572 0.487341 0.763454 11.00000 0.03198 0.02686 = 0.03768 -0.00855 -0.00575 -0.00935 C27 1 0.440920 0.586503 0.781974 11.00000 0.03948 0.02788 = 0.05245 -0.00694 -0.00257 -0.00835 AFIX 43 H27 2 0.461751 0.642801 0.741429 11.00000 -1.20000 AFIX 0 C28 1 0.365711 0.603614 0.858710 11.00000 0.04178 0.03112 = 0.06018 -0.02020 -0.00811 -0.00552 AFIX 43 H28 2 0.335312 0.671253 0.870376 11.00000 -1.20000 AFIX 0 C29 1 0.335069 0.522260 0.918120 11.00000 0.03572 0.03830 = 0.03824 -0.01701 -0.00684 -0.00066 AFIX 43 H29 2 0.283567 0.535073 0.970414 11.00000 -1.20000 AFIX 0 C30 1 0.377710 0.421640 0.903446 11.00000 0.02693 0.03363 = 0.02970 -0.00916 -0.00994 -0.00200 C31 1 0.338877 0.334142 0.967911 11.00000 0.03617 0.04091 = 0.02839 -0.00636 -0.00639 0.00144 AFIX 13 H31 2 0.397945 0.272032 0.956378 11.00000 -1.20000 AFIX 0 C32 1 0.218648 0.313083 0.958595 11.00000 0.04847 0.06498 = 0.03994 -0.00295 -0.00236 -0.02354 AFIX 137 H32A 2 0.197852 0.253103 0.998251 11.00000 -1.50000 H32B 2 0.222750 0.300589 0.900074 11.00000 -1.50000 H32C 2 0.158556 0.372108 0.971511 11.00000 -1.50000 AFIX 0 C33 1 0.333236 0.352237 1.060813 11.00000 0.05760 0.06216 = 0.03000 -0.01226 -0.00631 0.00354 AFIX 137 H33A 2 0.319295 0.289800 1.099446 11.00000 -1.50000 H33B 2 0.268796 0.407349 1.076175 11.00000 -1.50000 H33C 2 0.408051 0.370999 1.065544 11.00000 -1.50000 AFIX 0 C34 1 0.569417 0.471060 0.678652 11.00000 0.04073 0.03157 = 0.03587 -0.00438 0.00145 -0.00943 AFIX 13 H34 2 0.569617 0.400007 0.668020 11.00000 -1.20000 AFIX 0 C35 1 0.694538 0.480790 0.682837 11.00000 0.03612 0.06439 = 0.05276 0.00995 -0.00208 -0.00421 AFIX 137 H35A 2 0.745792 0.472418 0.627277 11.00000 -1.50000 H35B 2 0.722764 0.428112 0.726251 11.00000 -1.50000 H35C 2 0.695875 0.548124 0.697686 11.00000 -1.50000 AFIX 0 C36 1 0.531307 0.543671 0.602866 11.00000 0.04109 0.04342 = 0.04182 -0.00098 -0.01024 -0.01171 AFIX 137 H36A 2 0.578490 0.521385 0.549590 11.00000 -1.50000 H36B 2 0.543382 0.612722 0.606573 11.00000 -1.50000 H36C 2 0.447692 0.543312 0.603999 11.00000 -1.50000 AFIX 0 C37 1 0.264707 0.187559 0.747290 11.00000 0.03158 0.02410 = 0.04163 -0.00096 -0.01356 -0.00598 AFIX 43 H37 2 0.286401 0.121779 0.776134 11.00000 -1.20000 AFIX 0 C38 1 0.162576 0.207079 0.717691 11.00000 0.02828 0.02999 = 0.03925 -0.00107 -0.01072 -0.00905 AFIX 43 H38 2 0.114490 0.155313 0.726868 11.00000 -1.20000 AFIX 0 C39 1 0.125951 0.303706 0.673093 11.00000 0.02694 0.02617 = 0.02249 -0.00334 -0.00401 -0.00401 C40 1 0.204843 0.376671 0.662402 11.00000 0.02652 0.02678 = 0.03074 -0.00257 -0.00836 -0.00374 AFIX 43 H40 2 0.186433 0.442659 0.632806 11.00000 -1.20000 AFIX 0 C41 1 0.304847 0.352063 0.694117 11.00000 0.03008 0.02524 = 0.03023 -0.00507 -0.00653 -0.00752 AFIX 43 H41 2 0.354888 0.402176 0.686006 11.00000 -1.20000 AFIX 0 C42 1 -0.053044 0.251397 0.653947 11.00000 0.03591 0.03893 = 0.03981 0.00192 -0.01767 -0.01271 AFIX 137 H42A 2 -0.116416 0.279377 0.622257 11.00000 -1.50000 H42B 2 -0.086964 0.236691 0.714604 11.00000 -1.50000 H42C 2 -0.009747 0.188496 0.632520 11.00000 -1.50000 AFIX 0 C43 1 -0.002302 0.425099 0.593264 11.00000 0.03407 0.03424 = 0.04405 0.00462 -0.01650 -0.00637 AFIX 137 H43A 2 -0.061612 0.420671 0.560387 11.00000 -1.50000 H43B 2 0.068596 0.444571 0.554286 11.00000 -1.50000 H43C 2 -0.034034 0.476341 0.632161 11.00000 -1.50000 AFIX 0 C44 1 0.128038 0.223588 0.407010 11.00000 0.03925 0.05075 = 0.05069 -0.01038 -0.01304 -0.00658 AFIX 23 H44A 2 0.137885 0.148398 0.418873 11.00000 -1.20000 H44B 2 0.044780 0.250406 0.429437 11.00000 -1.20000 AFIX 0 C45 1 0.114163 -0.131700 0.665431 11.00000 0.03857 0.04577 = 0.04241 -0.01281 -0.01075 -0.00468 AFIX 23 H45A 2 0.062036 -0.167631 0.712659 11.00000 -1.20000 H45B 2 0.149897 -0.179488 0.623241 11.00000 -1.20000 AFIX 0 C46 1 1.093751 0.582867 0.793280 11.00000 0.04749 0.04767 = 0.03373 -0.00620 -0.00403 -0.00707 AFIX 23 H46A 2 1.094444 0.614853 0.733700 11.00000 -1.20000 H46B 2 1.174205 0.546938 0.797034 11.00000 -1.20000 AFIX 0 HKLF 4 REM 2_a.res in P-1 REM R1 = 0.0570 for 7074 Fo > 4sig(Fo) and 0.0928 for all 9941 data REM 533 parameters refined using 0 restraints END WGHT 0.0659 4.5734 REM Highest difference peak 0.718, deepest hole -0.682, 1-sigma level 0.099 Q1 1 0.1716 0.6362 0.6200 11.00000 0.05 0.72 Q2 1 0.2487 -0.0347 0.6574 11.00000 0.05 0.71 Q3 1 0.2068 0.6517 0.4978 11.00000 0.05 0.66 Q4 1 0.0639 -0.0166 0.5419 11.00000 0.05 0.53 Q5 1 0.6251 0.2936 0.4994 11.00000 0.05 0.53 Q6 1 0.4762 -0.0354 0.8433 11.00000 0.05 0.46 Q7 1 0.0003 0.5768 0.6142 11.00000 0.05 0.46 Q8 1 0.1645 0.5574 0.6181 11.00000 0.05 0.44 Q9 1 0.1836 0.5458 0.6043 11.00000 0.05 0.44 Q10 1 1.1212 0.7142 0.8289 11.00000 0.05 0.41 Q11 1 0.2658 0.5768 0.4952 11.00000 0.05 0.41 Q12 1 0.2070 0.2426 0.5239 11.00000 0.05 0.39 Q13 1 1.0305 0.5452 0.8576 11.00000 0.05 0.39 Q14 1 0.1470 0.3997 1.0778 11.00000 0.05 0.38 Q15 1 0.8262 0.1282 0.4617 11.00000 0.05 0.37 Q16 1 0.2034 0.7231 0.5034 11.00000 0.05 0.37 Q17 1 1.1153 0.7378 0.8978 11.00000 0.05 0.34 Q18 1 0.1527 0.7368 0.5517 11.00000 0.05 0.34 Q19 1 0.9737 0.3862 0.8116 11.00000 0.05 0.34 Q20 1 0.3570 0.3833 0.9317 11.00000 0.05 0.34 ; _shelx_res_checksum 40314 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.18277(4) 0.63934(3) 0.55729(3) 0.03187(13) Uani 1 1 d . . . . . N1 N 0.5206(3) 0.1376(2) 0.77607(19) 0.0230(7) Uani 1 1 d . . . . . B1 B 0.4474(4) 0.2350(3) 0.7721(3) 0.0239(9) Uani 1 1 d . . . . . Cl1 Cl 0.22038(11) 0.26901(12) 0.46034(8) 0.0530(3) Uani 1 1 d . . . . . C1 C 0.8929(4) -0.0341(4) 0.8533(3) 0.0345(10) Uani 1 1 d . . . . . H1 H 0.934480 -0.101173 0.849601 0.041 Uiso 1 1 calc R U . . . C2 C 0.9415(4) 0.0327(3) 0.8861(3) 0.0327(9) Uani 1 1 d . . . . . H2 H 1.015196 0.011740 0.903662 0.039 Uiso 1 1 calc R U . . . Cl2 Cl 0.15983(12) 0.25991(12) 0.29603(8) 0.0556(4) Uani 1 1 d . . . . . N2 N 0.4988(3) 0.3023(2) 0.80760(19) 0.0229(7) Uani 1 1 d . . . . . Cl3 Cl 0.02907(12) -0.02618(10) 0.61685(9) 0.0534(3) Uani 1 1 d . . . . . N3 N 0.3382(3) 0.2586(2) 0.7375(2) 0.0258(7) Uani 1 1 d . . . . . C3 C 0.8809(4) 0.1331(3) 0.8937(2) 0.0289(9) Uani 1 1 d . . . . . C4 C 0.9167(4) 0.2117(4) 0.9270(3) 0.0321(9) Uani 1 1 d . . . . . H4 H 0.988737 0.199294 0.947254 0.039 Uiso 1 1 calc R U . . . Cl4 Cl 0.22531(13) -0.09731(15) 0.70506(12) 0.0749(5) Uani 1 1 d . . . . . N4 N 0.0279(3) 0.3258(3) 0.6427(2) 0.0279(7) Uani 1 1 d . . . . . Cl5 Cl 0.99425(12) 0.49444(11) 0.82043(9) 0.0577(4) Uani 1 1 d . . . . . C5 C 0.8474(4) 0.3050(4) 0.9297(3) 0.0343(10) Uani 1 1 d . . . . . H5 H 0.872778 0.355817 0.952594 0.041 Uiso 1 1 calc R U . . . C6 C 0.7396(4) 0.3293(3) 0.9000(3) 0.0296(9) Uani 1 1 d . . . . . H6 H 0.693739 0.394935 0.903003 0.035 Uiso 1 1 calc R U . . . Cl6 Cl 1.05479(12) 0.67852(10) 0.86160(8) 0.0512(3) Uani 1 1 d . . . . . C7 C 0.7030(3) 0.2565(3) 0.8671(2) 0.0254(8) Uani 1 1 d . . . . . C8 C 0.7751(3) 0.1585(3) 0.8651(2) 0.0246(8) Uani 1 1 d . . . . . C9 C 0.7245(3) 0.0892(3) 0.8305(2) 0.0246(8) Uani 1 1 d . . . . . C10 C 0.7847(4) -0.0080(3) 0.8250(3) 0.0299(9) Uani 1 1 d . . . . . H10 H 0.754039 -0.056303 0.802700 0.036 Uiso 1 1 calc R U . . . C11 C 0.6158(3) 0.1495(3) 0.8102(2) 0.0248(8) Uani 1 1 d . . . . . C12 C 0.6025(3) 0.2464(3) 0.8294(2) 0.0241(8) Uani 1 1 d . . . . . C13 C 0.5205(3) 0.0453(3) 0.7412(2) 0.0236(8) Uani 1 1 d . . . . . C14 C 0.4756(3) -0.0362(3) 0.7952(2) 0.0263(8) Uani 1 1 d . . . . . C15 C 0.4839(4) -0.1264(3) 0.7606(3) 0.0289(9) Uani 1 1 d . . . . . H15 H 0.455554 -0.183765 0.795955 0.035 Uiso 1 1 calc R U . . . C17 C 0.5750(4) -0.0504(3) 0.6230(2) 0.0295(9) Uani 1 1 d . . . . . H17 H 0.607849 -0.056285 0.564769 0.035 Uiso 1 1 calc R U . . . C16 C 0.5326(4) -0.1331(3) 0.6759(3) 0.0313(9) Uani 1 1 d . . . . . H16 H 0.537238 -0.194859 0.653458 0.038 Uiso 1 1 calc R U . . . C18 C 0.5699(3) 0.0415(3) 0.6543(2) 0.0264(8) Uani 1 1 d . . . . . C19 C 0.6218(4) 0.1299(3) 0.5975(2) 0.0288(9) Uani 1 1 d . . . . . H19 H 0.605517 0.188083 0.631692 0.035 Uiso 1 1 calc R U . . . C20 C 0.5655(5) 0.1657(4) 0.5190(3) 0.0516(13) Uani 1 1 d . . . . . H20A H 0.597703 0.225845 0.486859 0.077 Uiso 1 1 calc R U . . . H20B H 0.479952 0.183072 0.537050 0.077 Uiso 1 1 calc R U . . . H20C H 0.582742 0.111178 0.482868 0.077 Uiso 1 1 calc R U . . . C21 C 0.7548(4) 0.1021(4) 0.5733(4) 0.0498(13) Uani 1 1 d . . . . . H21A H 0.788181 0.160824 0.539363 0.075 Uiso 1 1 calc R U . . . H21B H 0.773816 0.044941 0.539748 0.075 Uiso 1 1 calc R U . . . H21C H 0.788199 0.082577 0.625046 0.075 Uiso 1 1 calc R U . . . C22 C 0.4184(4) -0.0292(3) 0.8884(3) 0.0305(9) Uani 1 1 d . . . . . H22 H 0.416614 0.041767 0.899992 0.037 Uiso 1 1 calc R U . . . C23 C 0.2911(4) -0.0518(4) 0.9086(3) 0.0371(10) Uani 1 1 d . . . . . H23A H 0.254673 -0.039242 0.967077 0.056 Uiso 1 1 calc R U . . . H23B H 0.291490 -0.123058 0.902802 0.056 Uiso 1 1 calc R U . . . H23C H 0.245952 -0.007367 0.868848 0.056 Uiso 1 1 calc R U . . . C24 C 0.4890(4) -0.1019(4) 0.9477(3) 0.0366(10) Uani 1 1 d . . . . . H24A H 0.450986 -0.095149 1.006977 0.055 Uiso 1 1 calc R U . . . H24B H 0.569187 -0.085547 0.937313 0.055 Uiso 1 1 calc R U . . . H24C H 0.492438 -0.171972 0.936913 0.055 Uiso 1 1 calc R U . . . C25 C 0.4546(3) 0.4064(3) 0.8253(3) 0.0263(8) Uani 1 1 d . . . . . C26 C 0.4866(4) 0.4873(3) 0.7635(3) 0.0312(9) Uani 1 1 d . . . . . C27 C 0.4409(4) 0.5865(3) 0.7820(3) 0.0403(11) Uani 1 1 d . . . . . H27 H 0.461751 0.642801 0.741429 0.048 Uiso 1 1 calc R U . . . C28 C 0.3657(4) 0.6036(4) 0.8587(3) 0.0430(12) Uani 1 1 d . . . . . H28 H 0.335312 0.671253 0.870376 0.052 Uiso 1 1 calc R U . . . C29 C 0.3351(4) 0.5223(4) 0.9181(3) 0.0367(10) Uani 1 1 d . . . . . H29 H 0.283567 0.535073 0.970414 0.044 Uiso 1 1 calc R U . . . C30 C 0.3777(3) 0.4216(3) 0.9034(3) 0.0291(9) Uani 1 1 d . . . . . C31 C 0.3389(4) 0.3341(4) 0.9679(3) 0.0359(10) Uani 1 1 d . . . . . H31 H 0.397945 0.272032 0.956378 0.043 Uiso 1 1 calc R U . . . C32 C 0.2186(5) 0.3131(5) 0.9586(3) 0.0506(13) Uani 1 1 d . . . . . H32A H 0.197852 0.253103 0.998251 0.076 Uiso 1 1 calc R U . . . H32B H 0.222750 0.300589 0.900074 0.076 Uiso 1 1 calc R U . . . H32C H 0.158556 0.372108 0.971511 0.076 Uiso 1 1 calc R U . . . C33 C 0.3332(5) 0.3522(4) 1.0608(3) 0.0512(13) Uani 1 1 d . . . . . H33A H 0.319295 0.289800 1.099446 0.077 Uiso 1 1 calc R U . . . H33B H 0.268796 0.407349 1.076175 0.077 Uiso 1 1 calc R U . . . H33C H 0.408051 0.370999 1.065544 0.077 Uiso 1 1 calc R U . . . C34 C 0.5694(4) 0.4711(3) 0.6787(3) 0.0369(10) Uani 1 1 d . . . . . H34 H 0.569617 0.400007 0.668020 0.044 Uiso 1 1 calc R U . . . C35 C 0.6945(4) 0.4808(5) 0.6828(4) 0.0546(14) Uani 1 1 d . . . . . H35A H 0.745792 0.472418 0.627277 0.082 Uiso 1 1 calc R U . . . H35B H 0.722764 0.428112 0.726251 0.082 Uiso 1 1 calc R U . . . H35C H 0.695875 0.548124 0.697686 0.082 Uiso 1 1 calc R U . . . C36 C 0.5313(4) 0.5437(4) 0.6029(3) 0.0416(11) Uani 1 1 d . . . . . H36A H 0.578490 0.521385 0.549590 0.062 Uiso 1 1 calc R U . . . H36B H 0.543382 0.612722 0.606573 0.062 Uiso 1 1 calc R U . . . H36C H 0.447692 0.543312 0.603999 0.062 Uiso 1 1 calc R U . . . C37 C 0.2647(4) 0.1876(3) 0.7473(3) 0.0316(9) Uani 1 1 d . . . . . H37 H 0.286401 0.121779 0.776134 0.038 Uiso 1 1 calc R U . . . C38 C 0.1626(4) 0.2071(3) 0.7177(3) 0.0317(9) Uani 1 1 d . . . . . H38 H 0.114490 0.155313 0.726868 0.038 Uiso 1 1 calc R U . . . C39 C 0.1260(3) 0.3037(3) 0.6731(2) 0.0253(8) Uani 1 1 d . . . . . C40 C 0.2048(3) 0.3767(3) 0.6624(3) 0.0278(8) Uani 1 1 d . . . . . H40 H 0.186433 0.442659 0.632806 0.033 Uiso 1 1 calc R U . . . C41 C 0.3048(4) 0.3521(3) 0.6941(3) 0.0278(9) Uani 1 1 d . . . . . H41 H 0.354888 0.402176 0.686006 0.033 Uiso 1 1 calc R U . . . C42 C -0.0530(4) 0.2514(4) 0.6539(3) 0.0365(10) Uani 1 1 d . . . . . H42A H -0.116416 0.279377 0.622257 0.055 Uiso 1 1 calc R U . . . H42B H -0.086964 0.236691 0.714604 0.055 Uiso 1 1 calc R U . . . H42C H -0.009747 0.188496 0.632520 0.055 Uiso 1 1 calc R U . . . C43 C -0.0023(4) 0.4251(3) 0.5933(3) 0.0370(10) Uani 1 1 d . . . . . H43A H -0.061612 0.420671 0.560387 0.056 Uiso 1 1 calc R U . . . H43B H 0.068596 0.444571 0.554286 0.056 Uiso 1 1 calc R U . . . H43C H -0.034034 0.476341 0.632161 0.056 Uiso 1 1 calc R U . . . C44 C 0.1280(4) 0.2236(4) 0.4070(3) 0.0458(12) Uani 1 1 d . . . . . H44A H 0.137885 0.148398 0.418873 0.055 Uiso 1 1 calc R U . . . H44B H 0.044780 0.250406 0.429437 0.055 Uiso 1 1 calc R U . . . C45 C 0.1142(4) -0.1317(4) 0.6654(3) 0.0412(11) Uani 1 1 d . . . . . H45A H 0.062036 -0.167631 0.712659 0.049 Uiso 1 1 calc R U . . . H45B H 0.149897 -0.179488 0.623241 0.049 Uiso 1 1 calc R U . . . C46 C 1.0938(4) 0.5829(4) 0.7933(3) 0.0435(11) Uani 1 1 d . . . . . H46A H 1.094444 0.614853 0.733700 0.052 Uiso 1 1 calc R U . . . H46B H 1.174205 0.546938 0.797034 0.052 Uiso 1 1 calc R U . . . 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 0.0347(2) 0.0304(2) 0.0328(2) -0.00227(17) -0.00987(17) -0.00833(17) N1 0.0268(16) 0.0221(17) 0.0223(16) -0.0043(13) -0.0066(13) -0.0056(13) B1 0.025(2) 0.027(2) 0.020(2) -0.0052(18) -0.0025(17) -0.0044(18) Cl1 0.0427(7) 0.0750(9) 0.0460(7) -0.0264(7) -0.0050(5) -0.0088(6) C1 0.034(2) 0.035(2) 0.033(2) -0.0059(19) -0.0058(18) 0.0021(19) C2 0.027(2) 0.040(3) 0.030(2) -0.0036(19) -0.0074(17) -0.0025(18) Cl2 0.0491(7) 0.0735(10) 0.0475(7) -0.0131(7) -0.0142(6) -0.0072(7) N2 0.0224(16) 0.0241(17) 0.0235(16) -0.0060(13) -0.0053(13) -0.0033(13) Cl3 0.0532(8) 0.0477(8) 0.0578(8) -0.0089(6) -0.0151(6) 0.0028(6) N3 0.0276(17) 0.0258(18) 0.0266(17) -0.0050(14) -0.0065(13) -0.0078(14) C3 0.027(2) 0.038(2) 0.0217(19) -0.0038(17) -0.0031(16) -0.0073(18) C4 0.024(2) 0.047(3) 0.028(2) -0.0059(19) -0.0063(16) -0.0092(19) Cl4 0.0527(8) 0.0970(13) 0.0923(12) -0.0356(10) -0.0325(8) -0.0131(8) N4 0.0257(17) 0.0299(19) 0.0297(18) -0.0027(15) -0.0075(14) -0.0064(14) Cl5 0.0524(8) 0.0543(8) 0.0598(8) -0.0052(7) 0.0048(6) -0.0120(6) C5 0.036(2) 0.042(3) 0.032(2) -0.0105(19) -0.0081(18) -0.016(2) C6 0.029(2) 0.033(2) 0.028(2) -0.0084(18) -0.0037(17) -0.0069(18) Cl6 0.0598(8) 0.0512(8) 0.0392(6) -0.0120(6) -0.0109(6) 0.0075(6) C7 0.028(2) 0.030(2) 0.0192(18) -0.0037(16) -0.0024(15) -0.0085(17) C8 0.0246(19) 0.032(2) 0.0185(18) -0.0035(16) -0.0037(15) -0.0076(17) C9 0.027(2) 0.029(2) 0.0180(18) -0.0017(16) -0.0038(15) -0.0048(16) C10 0.032(2) 0.029(2) 0.029(2) -0.0059(17) -0.0063(17) -0.0043(18) C11 0.029(2) 0.027(2) 0.0196(18) -0.0030(16) -0.0047(15) -0.0084(16) C12 0.0223(19) 0.029(2) 0.0215(18) -0.0052(16) -0.0022(15) -0.0052(16) C13 0.0260(19) 0.024(2) 0.0242(19) -0.0052(15) -0.0088(15) -0.0046(16) C14 0.026(2) 0.028(2) 0.026(2) -0.0053(16) -0.0077(16) -0.0049(16) C15 0.031(2) 0.026(2) 0.030(2) -0.0003(17) -0.0067(17) -0.0084(17) C17 0.032(2) 0.037(2) 0.023(2) -0.0113(18) -0.0027(16) -0.0099(18) C16 0.035(2) 0.028(2) 0.034(2) -0.0111(18) -0.0053(18) -0.0083(18) C18 0.0215(19) 0.032(2) 0.027(2) -0.0066(17) -0.0068(15) -0.0043(16) C19 0.033(2) 0.030(2) 0.024(2) -0.0019(17) -0.0049(16) -0.0082(18) C20 0.053(3) 0.057(3) 0.050(3) 0.017(3) -0.026(2) -0.024(3) C21 0.033(3) 0.049(3) 0.062(3) 0.013(3) -0.005(2) -0.013(2) C22 0.036(2) 0.030(2) 0.026(2) -0.0036(17) -0.0038(17) -0.0075(18) C23 0.034(2) 0.044(3) 0.028(2) 0.0017(19) -0.0011(18) -0.005(2) C24 0.041(2) 0.043(3) 0.027(2) -0.0014(19) -0.0087(18) -0.008(2) C25 0.0249(19) 0.026(2) 0.031(2) -0.0087(17) -0.0088(16) -0.0038(16) C26 0.032(2) 0.027(2) 0.038(2) -0.0086(18) -0.0057(18) -0.0093(18) C27 0.039(3) 0.028(2) 0.052(3) -0.007(2) -0.003(2) -0.008(2) C28 0.042(3) 0.031(3) 0.060(3) -0.020(2) -0.008(2) -0.006(2) C29 0.036(2) 0.038(3) 0.038(2) -0.017(2) -0.0068(19) -0.001(2) C30 0.027(2) 0.034(2) 0.030(2) -0.0092(18) -0.0099(17) -0.0020(17) C31 0.036(2) 0.041(3) 0.028(2) -0.0064(19) -0.0064(18) 0.001(2) C32 0.048(3) 0.065(4) 0.040(3) -0.003(2) -0.002(2) -0.024(3) C33 0.058(3) 0.062(4) 0.030(2) -0.012(2) -0.006(2) 0.004(3) C34 0.041(3) 0.032(2) 0.036(2) -0.0044(19) 0.0014(19) -0.009(2) C35 0.036(3) 0.064(4) 0.053(3) 0.010(3) -0.002(2) -0.004(2) C36 0.041(3) 0.043(3) 0.042(3) -0.001(2) -0.010(2) -0.012(2) C37 0.032(2) 0.024(2) 0.042(2) -0.0010(18) -0.0136(18) -0.0060(17) C38 0.028(2) 0.030(2) 0.039(2) -0.0011(19) -0.0107(18) -0.0090(18) C39 0.027(2) 0.026(2) 0.0225(19) -0.0033(16) -0.0040(15) -0.0040(16) C40 0.027(2) 0.027(2) 0.031(2) -0.0026(17) -0.0084(16) -0.0037(17) C41 0.030(2) 0.025(2) 0.030(2) -0.0051(17) -0.0065(17) -0.0075(17) C42 0.036(2) 0.039(3) 0.040(2) 0.002(2) -0.0177(19) -0.013(2) C43 0.034(2) 0.034(3) 0.044(3) 0.005(2) -0.017(2) -0.0064(19) C44 0.039(3) 0.051(3) 0.051(3) -0.010(2) -0.013(2) -0.007(2) C45 0.039(3) 0.046(3) 0.042(3) -0.013(2) -0.011(2) -0.005(2) C46 0.047(3) 0.048(3) 0.034(2) -0.006(2) -0.004(2) -0.007(2) 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' N N 0.0061 0.0033 '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' Br Br -0.2901 2.4595 '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 C11 N1 B1 105.9(3) . . ? C11 N1 C13 120.8(3) . . ? B1 N1 C13 132.5(3) . . ? N2 B1 N1 108.1(3) . . ? N2 B1 N3 127.3(4) . . ? N1 B1 N3 124.6(3) . . ? C2 C1 C10 123.3(4) . . ? C2 C1 H1 118.3 . . ? C10 C1 H1 118.3 . . ? C1 C2 C3 119.8(4) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C12 N2 B1 106.1(3) . . ? C12 N2 C25 123.6(3) . . ? B1 N2 C25 130.1(3) . . ? C37 N3 C41 116.8(3) . . ? C37 N3 B1 121.3(4) . . ? C41 N3 B1 122.0(3) . . ? C8 C3 C2 116.6(4) . . ? C8 C3 C4 115.9(4) . . ? C2 C3 C4 127.5(4) . . ? C5 C4 C3 120.0(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C39 N4 C43 120.8(3) . . ? C39 N4 C42 121.6(4) . . ? C43 N4 C42 117.5(3) . . ? C4 C5 C6 123.1(4) . . ? C4 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C7 C6 C5 118.5(4) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C6 C7 C8 118.3(4) . . ? C6 C7 C12 137.9(4) . . ? C8 C7 C12 103.8(3) . . ? C3 C8 C7 124.1(4) . . ? C3 C8 C9 123.7(4) . . ? C7 C8 C9 112.1(3) . . ? C10 C9 C8 118.3(4) . . ? C10 C9 C11 138.2(4) . . ? C8 C9 C11 103.5(3) . . ? C9 C10 C1 118.2(4) . . ? C9 C10 H10 120.9 . . ? C1 C10 H10 120.9 . . ? C12 C11 N1 110.1(3) . . ? C12 C11 C9 111.4(3) . . ? N1 C11 C9 138.5(4) . . ? C11 C12 N2 109.8(3) . . ? C11 C12 C7 109.1(3) . . ? N2 C12 C7 141.1(4) . . ? C14 C13 C18 123.2(3) . . ? C14 C13 N1 119.1(3) . . ? C18 C13 N1 117.7(3) . . ? C13 C14 C15 117.5(3) . . ? C13 C14 C22 122.4(3) . . ? C15 C14 C22 120.1(4) . . ? C16 C15 C14 120.8(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C16 C17 C18 121.0(4) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C17 C16 C15 120.7(4) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C13 C18 C17 116.8(4) . . ? C13 C18 C19 122.3(3) . . ? C17 C18 C19 120.8(3) . . ? C18 C19 C21 109.9(4) . . ? C18 C19 C20 112.7(3) . . ? C21 C19 C20 111.7(4) . . ? C18 C19 H19 107.4 . . ? C21 C19 H19 107.4 . . ? C20 C19 H19 107.4 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C24 C22 C14 111.2(4) . . ? C24 C22 C23 109.0(4) . . ? C14 C22 C23 112.0(3) . . ? C24 C22 H22 108.2 . . ? C14 C22 H22 108.2 . . ? C23 C22 H22 108.2 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C30 122.4(4) . . ? C26 C25 N2 119.2(3) . . ? C30 C25 N2 118.3(4) . . ? C25 C26 C27 117.8(4) . . ? C25 C26 C34 122.6(4) . . ? C27 C26 C34 119.7(4) . . ? C26 C27 C28 120.9(4) . . ? C26 C27 H27 119.5 . . ? C28 C27 H27 119.5 . . ? C29 C28 C27 120.0(4) . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C28 C29 C30 121.8(4) . . ? C28 C29 H29 119.1 . . ? C30 C29 H29 119.1 . . ? C29 C30 C25 117.1(4) . . ? C29 C30 C31 120.7(4) . . ? C25 C30 C31 122.2(4) . . ? C30 C31 C32 110.9(4) . . ? C30 C31 C33 112.5(4) . . ? C32 C31 C33 109.6(4) . . ? C30 C31 H31 107.9 . . ? C32 C31 H31 107.9 . . ? C33 C31 H31 107.9 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C26 110.7(4) . . ? C35 C34 C36 109.4(4) . . ? C26 C34 C36 113.4(4) . . ? C35 C34 H34 107.7 . . ? C26 C34 H34 107.7 . . ? C36 C34 H34 107.7 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C38 C37 N3 122.9(4) . . ? C38 C37 H37 118.5 . . ? N3 C37 H37 118.5 . . ? C37 C38 C39 121.2(4) . . ? C37 C38 H38 119.4 . . ? C39 C38 H38 119.4 . . ? N4 C39 C38 123.3(4) . . ? N4 C39 C40 121.6(4) . . ? C38 C39 C40 115.1(4) . . ? C41 C40 C39 120.4(4) . . ? C41 C40 H40 119.8 . . ? C39 C40 H40 119.8 . . ? C40 C41 N3 123.6(4) . . ? C40 C41 H41 118.2 . . ? N3 C41 H41 118.2 . . ? N4 C42 H42A 109.5 . . ? N4 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? N4 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? N4 C43 H43A 109.5 . . ? N4 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? N4 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? Cl2 C44 Cl1 112.2(3) . . ? Cl2 C44 H44A 109.2 . . ? Cl1 C44 H44A 109.2 . . ? Cl2 C44 H44B 109.2 . . ? Cl1 C44 H44B 109.2 . . ? H44A C44 H44B 107.9 . . ? Cl4 C45 Cl3 112.5(3) . . ? Cl4 C45 H45A 109.1 . . ? Cl3 C45 H45A 109.1 . . ? Cl4 C45 H45B 109.1 . . ? Cl3 C45 H45B 109.1 . . ? H45A C45 H45B 107.8 . . ? Cl5 C46 Cl6 111.4(3) . . ? Cl5 C46 H46A 109.3 . . ? Cl6 C46 H46A 109.3 . . ? Cl5 C46 H46B 109.3 . . ? Cl6 C46 H46B 109.3 . . ? H46A C46 H46B 108.0 . . ? 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 N1 C11 1.395(5) . ? N1 B1 1.431(6) . ? N1 C13 1.448(5) . ? B1 N2 1.430(5) . ? B1 N3 1.472(5) . ? Cl1 C44 1.768(5) . ? C1 C2 1.377(6) . ? C1 C10 1.411(6) . ? C1 H1 0.9500 . ? C2 C3 1.420(6) . ? C2 H2 0.9500 . ? Cl2 C44 1.762(5) . ? N2 C12 1.394(5) . ? N2 C25 1.456(5) . ? Cl3 C45 1.760(5) . ? N3 C37 1.372(5) . ? N3 C41 1.373(5) . ? C3 C8 1.386(6) . ? C3 C4 1.430(6) . ? C4 C5 1.369(6) . ? C4 H4 0.9500 . ? Cl4 C45 1.737(5) . ? N4 C39 1.317(5) . ? N4 C43 1.468(6) . ? N4 C42 1.469(5) . ? Cl5 C46 1.760(5) . ? C5 C6 1.416(6) . ? C5 H5 0.9500 . ? C6 C7 1.364(5) . ? C6 H6 0.9500 . ? Cl6 C46 1.770(5) . ? C7 C8 1.434(6) . ? C7 C12 1.478(5) . ? C8 C9 1.435(5) . ? C9 C10 1.377(6) . ? C9 C11 1.455(6) . ? C10 H10 0.9500 . ? C11 C12 1.365(5) . ? C13 C14 1.396(6) . ? C13 C18 1.408(5) . ? C14 C15 1.399(6) . ? C14 C22 1.526(5) . ? C15 C16 1.380(6) . ? C15 H15 0.9500 . ? C17 C16 1.389(6) . ? C17 C18 1.401(6) . ? C17 H17 0.9500 . ? C16 H16 0.9500 . ? C18 C19 1.518(6) . ? C19 C21 1.518(6) . ? C19 C20 1.529(6) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C24 1.521(6) . ? C22 C23 1.536(6) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.402(6) . ? C25 C30 1.409(6) . ? C26 C27 1.401(6) . ? C26 C34 1.526(6) . ? C27 C28 1.388(7) . ? C27 H27 0.9500 . ? C28 C29 1.381(7) . ? C28 H28 0.9500 . ? C29 C30 1.397(6) . ? C29 H29 0.9500 . ? C30 C31 1.509(6) . ? C31 C32 1.534(7) . ? C31 C33 1.550(6) . ? C31 H31 1.0000 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.517(7) . ? C34 C36 1.533(7) . ? C34 H34 1.0000 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 C38 1.354(6) . ? C37 H37 0.9500 . ? C38 C39 1.423(6) . ? C38 H38 0.9500 . ? C39 C40 1.437(5) . ? C40 C41 1.349(6) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ?