#------------------------------------------------------------------------------ #$Date: 2019-11-30 03:27:22 +0200 (Sat, 30 Nov 2019) $ #$Revision: 244816 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125631.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_7125631 loop_ _publ_author_name 'Chai, Danyang' 'Zou, Yang' 'Xiang, Yepeng' 'Zeng, Xuan' 'Chen, Zhanxiang' 'Gong, Shaolong' 'Yang, Chuluo' _publ_section_title ; Fused twin-acridine scaffolds as electron donors for thermally activated delayed fluorescence emitters: controllable TADF behavior by methyl substitution ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC08679J _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_moiety 'C66 H50 N8' _chemical_formula_sum 'C66 H50 N8' _chemical_formula_weight 955.14 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_block_doi 10.5517/ccdc.csd.cc23tmn7 _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-10-24 deposited with the CCDC. 2019-11-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.850(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.1160(7) _cell_length_b 14.9218(10) _cell_length_c 15.4714(10) _cell_measurement_reflns_used 7478 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 68.20 _cell_measurement_theta_min 2.91 _cell_volume 2520.4(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 297(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_unetI/netI 0.0502 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 17684 _diffrn_reflns_point_group_measured_fraction_full 0.959 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_theta_full 65.070 _diffrn_reflns_theta_max 65.070 _diffrn_reflns_theta_min 2.908 _exptl_absorpt_coefficient_mu 0.583 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.6660 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.259 _exptl_crystal_description brick _exptl_crystal_F_000 1004 _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.155 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details ; Flack x determined using 2518 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.3(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 667 _refine_ls_number_reflns 8240 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0419 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.1276P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1004 _refine_ls_wR_factor_ref 0.1230 _reflns_Friedel_coverage 0.865 _reflns_Friedel_fraction_full 0.930 _reflns_Friedel_fraction_max 0.930 _reflns_number_gt 6618 _reflns_number_total 8240 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc08679j2.cif _cod_data_source_block 616 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7125631 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.933 _shelx_estimated_absorpt_t_max 0.955 _shelx_res_file ; TITL 616 in P2(1) 616.res created by SHELXL-2018/3 at 14:44:24 on 20-Aug-2019 CELL 1.54178 11.1160 14.9218 15.4714 90.000 100.850 90.000 ZERR 2.000 0.0007 0.0010 0.0010 0.000 0.003 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H N UNIT 132 100 16 TEMP 24.240 L.S. 4 ACTA CONF HTAB SIZE 0.08 0.10 0.12 BOND $H FMAP 2 PLAN 10 WGHT 0.052100 0.127600 FVAR 0.61307 N1 3 0.238288 0.657450 0.040920 11.00000 0.05009 0.04954 = 0.03760 -0.00644 -0.00237 0.00318 N2 3 0.333220 0.348405 -0.017914 11.00000 0.04194 0.04832 = 0.04620 -0.00832 -0.00209 0.00608 N3 3 0.670922 0.631173 0.379345 11.00000 0.04484 0.06772 = 0.04038 -0.00280 0.00064 -0.00232 N4 3 0.698052 0.630527 0.534274 11.00000 0.04943 0.06898 = 0.03890 0.00316 -0.00058 -0.00259 N5 3 0.498893 0.615554 0.448989 11.00000 0.04950 0.06224 = 0.04107 0.00262 0.00320 -0.00220 N6 3 0.792241 0.394622 0.301561 11.00000 0.04103 0.06334 = 0.04846 -0.00252 0.00360 0.00002 N7 3 0.829224 0.403314 0.457187 11.00000 0.04383 0.07398 = 0.04834 -0.00024 0.00201 0.00022 N8 3 0.628533 0.377502 0.378578 11.00000 0.04265 0.06942 = 0.04526 0.00191 0.00236 0.00044 C1 1 0.175048 0.737793 0.018754 11.00000 0.04666 0.05258 = 0.03753 0.00050 0.01045 0.00206 C2 1 0.202251 0.813434 0.072491 11.00000 0.07772 0.05811 = 0.04513 -0.00602 0.00389 0.00863 AFIX 43 H2A 2 0.263963 0.810119 0.122151 11.00000 -1.20000 AFIX 0 C3 1 0.139593 0.892255 0.053237 11.00000 0.10410 0.05413 = 0.05661 -0.00492 0.01396 0.00700 AFIX 43 H3B 2 0.159946 0.941766 0.089557 11.00000 -1.20000 AFIX 0 C4 1 0.047171 0.898919 -0.019033 11.00000 0.09300 0.05959 = 0.05682 0.00504 0.01735 0.02393 AFIX 43 H4B 2 0.002494 0.951659 -0.030736 11.00000 -1.20000 AFIX 0 C5 1 0.022138 0.826420 -0.073470 11.00000 0.06107 0.06615 = 0.04587 0.00947 0.00994 0.01748 AFIX 43 H5B 2 -0.038898 0.831624 -0.123356 11.00000 -1.20000 AFIX 0 C6 1 0.084506 0.744310 -0.057454 11.00000 0.04563 0.05337 = 0.03800 0.00551 0.01214 0.00437 C7 1 0.055318 0.667627 -0.122819 11.00000 0.04312 0.05283 = 0.04106 0.00307 0.00297 0.00190 C8 1 0.130475 0.584817 -0.092236 11.00000 0.03878 0.04895 = 0.03440 -0.00114 0.00455 0.00215 C9 1 0.115723 0.507459 -0.142899 11.00000 0.04114 0.06013 = 0.03353 -0.00550 -0.00388 0.00081 AFIX 43 H9A 2 0.058390 0.508872 -0.195091 11.00000 -1.20000 AFIX 0 C10 1 0.179622 0.428311 -0.121896 11.00000 0.03760 0.05474 = 0.03829 -0.00697 0.00007 0.00259 C11 1 0.166282 0.346946 -0.182157 11.00000 0.04957 0.06594 = 0.04001 -0.01200 0.00055 0.00222 C12 1 0.192823 0.263363 -0.126375 11.00000 0.05011 0.05856 = 0.04225 -0.01127 0.01461 -0.00566 C13 1 0.141325 0.179693 -0.152336 11.00000 0.07816 0.07135 = 0.05420 -0.01477 0.01459 -0.02602 AFIX 43 H13A 2 0.077708 0.176908 -0.200826 11.00000 -1.20000 AFIX 0 C14 1 0.180810 0.101570 -0.109204 11.00000 0.12966 0.06475 = 0.06690 -0.01102 0.02746 -0.03236 AFIX 43 H14A 2 0.144624 0.047199 -0.128641 11.00000 -1.20000 AFIX 0 C15 1 0.274242 0.104406 -0.037078 11.00000 0.12918 0.05112 = 0.06082 0.00021 0.02860 -0.01233 AFIX 43 H15A 2 0.303453 0.051567 -0.008811 11.00000 -1.20000 AFIX 0 C16 1 0.324834 0.185647 -0.006505 11.00000 0.07421 0.05808 = 0.04609 -0.00092 0.01623 0.00364 AFIX 43 H16A 2 0.386943 0.187272 0.043006 11.00000 -1.20000 AFIX 0 C17 1 0.283341 0.265528 -0.049468 11.00000 0.04677 0.05014 = 0.04410 -0.00912 0.01485 -0.00238 C18 1 0.265535 0.427794 -0.043322 11.00000 0.03699 0.04860 = 0.03983 -0.00649 0.00350 0.00170 C19 1 0.283435 0.504030 0.009001 11.00000 0.03932 0.05343 = 0.03994 -0.00590 -0.00470 0.00531 AFIX 43 H19A 2 0.340930 0.502605 0.061110 11.00000 -1.20000 AFIX 0 C20 1 0.217651 0.582557 -0.014419 11.00000 0.03769 0.05114 = 0.03511 -0.00338 0.00317 0.00169 C21 1 0.085950 0.697456 -0.211273 11.00000 0.12337 0.06628 = 0.03891 0.00421 0.01383 0.01231 AFIX 33 H21A 2 0.039177 0.749915 -0.231773 11.00000 -1.50000 H21B 2 0.171743 0.710935 -0.203688 11.00000 -1.50000 H21C 2 0.066062 0.650149 -0.253605 11.00000 -1.50000 AFIX 0 C22 1 -0.081774 0.644305 -0.135905 11.00000 0.04111 0.06426 = 0.13298 -0.00790 -0.00500 0.00633 AFIX 33 H22A 2 -0.129571 0.696623 -0.155271 11.00000 -1.50000 H22B 2 -0.100452 0.597944 -0.179384 11.00000 -1.50000 H22C 2 -0.100819 0.623798 -0.081224 11.00000 -1.50000 AFIX 0 C23 1 0.265402 0.351681 -0.239858 11.00000 0.10891 0.06336 = 0.05464 -0.00189 0.03528 0.00633 AFIX 33 H23A 2 0.252218 0.403954 -0.276596 11.00000 -1.50000 H23B 2 0.344896 0.354951 -0.202770 11.00000 -1.50000 H23C 2 0.260689 0.299080 -0.276067 11.00000 -1.50000 AFIX 0 C24 1 0.040831 0.344122 -0.242627 11.00000 0.08298 0.09373 = 0.09194 -0.04568 -0.03517 0.01953 AFIX 33 H24A 2 0.028295 0.398355 -0.276509 11.00000 -1.50000 H24B 2 0.037048 0.293691 -0.281574 11.00000 -1.50000 H24C 2 -0.021737 0.338544 -0.207823 11.00000 -1.50000 AFIX 0 C25 1 0.317080 0.648450 0.125532 11.00000 0.04767 0.04540 = 0.03532 -0.00633 -0.00169 -0.00064 C26 1 0.441994 0.649722 0.133542 11.00000 0.04693 0.07671 = 0.03601 -0.00567 0.00568 -0.00719 AFIX 43 H26A 2 0.476035 0.657349 0.083536 11.00000 -1.20000 AFIX 0 C27 1 0.518092 0.639918 0.214246 11.00000 0.03978 0.08178 = 0.04430 -0.00300 0.00381 -0.00667 AFIX 43 H27A 2 0.602601 0.640682 0.218148 11.00000 -1.20000 AFIX 0 C28 1 0.468937 0.628855 0.290105 11.00000 0.04402 0.05752 = 0.03664 -0.00368 -0.00035 -0.00640 C29 1 0.342977 0.628619 0.281604 11.00000 0.04496 0.08022 = 0.03955 0.00302 0.00724 -0.00259 AFIX 43 H29A 2 0.308537 0.622456 0.331603 11.00000 -1.20000 AFIX 0 C30 1 0.267147 0.637344 0.200413 11.00000 0.03773 0.08031 = 0.04461 -0.00135 0.00264 -0.00251 AFIX 43 H30A 2 0.182571 0.635766 0.195992 11.00000 -1.20000 AFIX 0 C31 1 0.550666 0.623803 0.377258 11.00000 0.04484 0.05725 = 0.03903 -0.00099 0.00132 -0.00207 C32 1 0.741055 0.634668 0.459342 11.00000 0.04669 0.05062 = 0.04116 0.00311 -0.00099 -0.00252 C33 1 0.577624 0.618698 0.525676 11.00000 0.04949 0.05873 = 0.04142 0.00079 0.00377 -0.00210 C34 1 0.874549 0.645928 0.464674 11.00000 0.04423 0.05640 = 0.04510 0.00520 -0.00104 -0.00099 C35 1 0.950137 0.669240 0.543637 11.00000 0.05221 0.09762 = 0.04739 -0.00437 -0.00037 -0.00560 AFIX 43 H35A 2 0.917674 0.674733 0.594568 11.00000 -1.20000 AFIX 0 C36 1 1.073202 0.684217 0.546458 11.00000 0.05203 0.09812 = 0.05811 -0.00060 -0.00933 -0.01118 AFIX 43 H36A 2 1.123339 0.700312 0.599289 11.00000 -1.20000 AFIX 0 C37 1 1.122362 0.675512 0.471628 11.00000 0.04301 0.07568 = 0.07131 0.01220 0.00251 -0.00292 AFIX 43 H37A 2 1.205158 0.686660 0.473645 11.00000 -1.20000 AFIX 0 C38 1 1.049118 0.650454 0.394453 11.00000 0.05018 0.07719 = 0.05812 0.01119 0.00805 0.00338 AFIX 43 H38A 2 1.082725 0.643159 0.344213 11.00000 -1.20000 AFIX 0 C39 1 0.925342 0.635825 0.390351 11.00000 0.04838 0.07463 = 0.04332 0.00846 -0.00126 -0.00062 AFIX 43 H39A 2 0.876107 0.619121 0.337359 11.00000 -1.20000 AFIX 0 C40 1 0.527421 0.610707 0.608089 11.00000 0.05603 0.05852 = 0.04243 0.00023 0.00721 0.00304 C41 1 0.603570 0.619888 0.688992 11.00000 0.07176 0.10492 = 0.04576 -0.00727 0.00629 -0.00901 AFIX 43 H41A 2 0.686275 0.632064 0.691841 11.00000 -1.20000 AFIX 0 C42 1 0.558668 0.611262 0.765171 11.00000 0.10399 0.12270 = 0.04390 -0.00885 0.01399 -0.00199 AFIX 43 H42A 2 0.611153 0.617236 0.819264 11.00000 -1.20000 AFIX 0 C43 1 0.436735 0.593861 0.762181 11.00000 0.10587 0.09521 = 0.05830 0.00415 0.03527 0.01278 AFIX 43 H43A 2 0.406431 0.588244 0.813999 11.00000 -1.20000 AFIX 0 C44 1 0.360567 0.584893 0.682905 11.00000 0.07219 0.09868 = 0.07752 0.02068 0.02924 0.01383 AFIX 43 H44A 2 0.277788 0.573514 0.680702 11.00000 -1.20000 AFIX 0 C45 1 0.405037 0.592537 0.605315 11.00000 0.06242 0.08420 = 0.05689 0.01402 0.01114 0.00365 AFIX 43 H45A 2 0.352419 0.585424 0.551426 11.00000 -1.20000 AFIX 0 C46 1 0.420586 0.351458 0.063348 11.00000 0.03707 0.05024 = 0.04389 -0.00265 -0.00068 0.00764 C47 1 0.543115 0.366112 0.062250 11.00000 0.04265 0.07378 = 0.04214 0.00213 0.00479 0.00195 AFIX 43 H47A 2 0.569892 0.370250 0.008947 11.00000 -1.20000 AFIX 0 C48 1 0.625075 0.374528 0.140111 11.00000 0.03563 0.07994 = 0.05293 0.00590 0.00504 0.00064 AFIX 43 H48A 2 0.707466 0.384014 0.139026 11.00000 -1.20000 AFIX 0 C49 1 0.587040 0.369116 0.220624 11.00000 0.03855 0.05648 = 0.04742 -0.00010 0.00221 0.00404 C50 1 0.464421 0.352581 0.220428 11.00000 0.04154 0.07855 = 0.04628 -0.00295 0.00768 0.00262 AFIX 43 H50A 2 0.437474 0.347577 0.273603 11.00000 -1.20000 AFIX 0 C51 1 0.381912 0.343454 0.142636 11.00000 0.03519 0.07764 = 0.05172 -0.00581 0.00474 -0.00017 AFIX 43 H51A 2 0.299944 0.331870 0.143511 11.00000 -1.20000 AFIX 0 C52 1 0.673921 0.381462 0.304741 11.00000 0.03974 0.05516 = 0.04537 0.00137 0.00219 0.00343 C53 1 0.866707 0.404604 0.379779 11.00000 0.04092 0.05876 = 0.04877 -0.00012 0.00248 -0.00016 C54 1 0.710069 0.389236 0.453073 11.00000 0.04409 0.05583 = 0.04632 0.00211 0.00066 0.00326 C55 1 0.999303 0.414431 0.381350 11.00000 0.04239 0.05811 = 0.05802 -0.00432 0.00200 -0.00053 C56 1 1.081873 0.411678 0.460863 11.00000 0.04604 0.09030 = 0.06822 0.00739 -0.00042 -0.00527 AFIX 43 H56A 2 1.053754 0.404725 0.513404 11.00000 -1.20000 AFIX 0 C57 1 1.205810 0.419311 0.461484 11.00000 0.04532 0.10976 = 0.09029 0.00202 -0.00821 -0.00571 AFIX 43 H57A 2 1.261093 0.417107 0.514645 11.00000 -1.20000 AFIX 0 C58 1 1.248007 0.430090 0.384582 11.00000 0.04062 0.10261 = 0.10691 -0.00560 0.01126 -0.00994 AFIX 43 H58A 2 1.331665 0.435255 0.385714 11.00000 -1.20000 AFIX 0 C59 1 1.167743 0.433280 0.306290 11.00000 0.05296 0.09209 = 0.08007 -0.01388 0.01924 -0.00944 AFIX 43 H59A 2 1.196872 0.440897 0.254222 11.00000 -1.20000 AFIX 0 C60 1 1.043707 0.425276 0.303927 11.00000 0.04921 0.07150 = 0.06299 -0.00502 0.00810 -0.00270 AFIX 43 H60A 2 0.989506 0.427144 0.250257 11.00000 -1.20000 AFIX 0 C61 1 0.665792 0.383825 0.537588 11.00000 0.04701 0.06498 = 0.04352 0.00636 0.00418 0.00749 C62 1 0.741849 0.405407 0.615407 11.00000 0.05328 0.12079 = 0.04816 0.00469 0.00538 -0.00159 AFIX 43 H62A 2 0.821590 0.424106 0.615148 11.00000 -1.20000 AFIX 0 C63 1 0.700728 0.399534 0.694061 11.00000 0.07476 0.13737 = 0.04611 0.00170 0.00394 0.00110 AFIX 43 H63A 2 0.753013 0.414257 0.746415 11.00000 -1.20000 AFIX 0 C64 1 0.583720 0.372234 0.695548 11.00000 0.07224 0.09287 = 0.05483 0.01769 0.01996 0.01572 AFIX 43 H64A 2 0.556445 0.368714 0.748705 11.00000 -1.20000 AFIX 0 C65 1 0.507497 0.350291 0.619283 11.00000 0.05933 0.07747 = 0.06935 0.01467 0.01785 0.00453 AFIX 43 H65A 2 0.427898 0.331828 0.620405 11.00000 -1.20000 AFIX 0 C66 1 0.547087 0.355141 0.540102 11.00000 0.05230 0.07073 = 0.05785 0.00332 0.00740 0.00183 AFIX 43 H66A 2 0.494490 0.339243 0.488259 11.00000 -1.20000 AFIX 0 HKLF 4 REM 616 in P2(1) REM wR2 = 0.1230, GooF = S = 1.073, Restrained GooF = 1.073 for all data REM R1 = 0.0419 for 6618 Fo > 4sig(Fo) and 0.0594 for all 8240 data REM 667 parameters refined using 1 restraints END WGHT 0.0518 0.1293 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.155, deepest hole -0.206, 1-sigma level 0.036 Q1 1 0.0808 0.3827 -0.3165 11.00000 0.05 0.16 Q2 1 1.1207 0.6224 0.6554 11.00000 0.05 0.15 Q3 1 0.7844 0.6988 0.6508 11.00000 0.05 0.13 Q4 1 0.7407 0.6291 0.5886 11.00000 0.05 0.13 Q5 1 0.2203 0.6662 -0.2010 11.00000 0.05 0.13 Q6 1 0.9212 0.6226 0.5028 11.00000 0.05 0.12 Q7 1 0.5391 0.4962 0.8342 11.00000 0.05 0.12 Q8 1 0.6119 0.3358 0.1865 11.00000 0.05 0.12 Q9 1 -0.0334 0.7406 -0.2326 11.00000 0.05 0.12 Q10 1 0.7122 0.6928 0.3006 11.00000 0.05 0.12 ; _shelx_res_checksum 97572 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 N1 N 0.2383(3) 0.6574(2) 0.04092(18) 0.0471(7) Uani 1 1 d . . N2 N 0.3332(3) 0.3484(2) -0.01791(18) 0.0468(7) Uani 1 1 d . . N3 N 0.6709(3) 0.6312(3) 0.37934(18) 0.0519(8) Uani 1 1 d . . N4 N 0.6981(3) 0.6305(3) 0.53427(18) 0.0536(8) Uani 1 1 d . . N5 N 0.4989(3) 0.6156(2) 0.44899(19) 0.0516(8) Uani 1 1 d . . N6 N 0.7922(3) 0.3946(3) 0.30156(19) 0.0516(8) Uani 1 1 d . . N7 N 0.8292(3) 0.4033(3) 0.4572(2) 0.0562(9) Uani 1 1 d . . N8 N 0.6285(3) 0.3775(3) 0.37858(19) 0.0532(8) Uani 1 1 d . . C1 C 0.1750(3) 0.7378(3) 0.0188(2) 0.0453(8) Uani 1 1 d . . C2 C 0.2023(4) 0.8134(3) 0.0725(3) 0.0613(11) Uani 1 1 d . . H2A H 0.263963 0.810119 0.122151 0.074 Uiso 1 1 calc R U C3 C 0.1396(5) 0.8923(4) 0.0532(3) 0.0718(13) Uani 1 1 d . . H3B H 0.159946 0.941766 0.089557 0.086 Uiso 1 1 calc R U C4 C 0.0472(5) 0.8989(4) -0.0190(3) 0.0694(12) Uani 1 1 d . . H4B H 0.002494 0.951659 -0.030736 0.083 Uiso 1 1 calc R U C5 C 0.0221(4) 0.8264(3) -0.0735(2) 0.0577(11) Uani 1 1 d . . H5B H -0.038898 0.831624 -0.123356 0.069 Uiso 1 1 calc R U C6 C 0.0845(3) 0.7443(3) -0.0575(2) 0.0451(8) Uani 1 1 d . . C7 C 0.0553(3) 0.6676(3) -0.1228(2) 0.0463(9) Uani 1 1 d . . C8 C 0.1305(3) 0.5848(3) -0.0922(2) 0.0410(8) Uani 1 1 d . . C9 C 0.1157(3) 0.5075(3) -0.1429(2) 0.0464(8) Uani 1 1 d . . H9A H 0.058390 0.508872 -0.195091 0.056 Uiso 1 1 calc R U C10 C 0.1796(3) 0.4283(3) -0.1219(2) 0.0445(8) Uani 1 1 d . . C11 C 0.1663(3) 0.3469(3) -0.1822(2) 0.0529(9) Uani 1 1 d . . C12 C 0.1928(3) 0.2634(3) -0.1264(2) 0.0495(9) Uani 1 1 d . . C13 C 0.1413(5) 0.1797(4) -0.1523(3) 0.0676(12) Uani 1 1 d . . H13A H 0.077708 0.176908 -0.200826 0.081 Uiso 1 1 calc R U C14 C 0.1808(6) 0.1016(4) -0.1092(3) 0.0859(17) Uani 1 1 d . . H14A H 0.144624 0.047199 -0.128641 0.103 Uiso 1 1 calc R U C15 C 0.2742(6) 0.1044(4) -0.0371(3) 0.0790(15) Uani 1 1 d . . H15A H 0.303453 0.051567 -0.008811 0.095 Uiso 1 1 calc R U C16 C 0.3248(4) 0.1856(3) -0.0065(2) 0.0588(10) Uani 1 1 d . . H16A H 0.386943 0.187272 0.043006 0.071 Uiso 1 1 calc R U C17 C 0.2833(3) 0.2655(3) -0.0495(2) 0.0462(8) Uani 1 1 d . . C18 C 0.2655(3) 0.4278(3) -0.0433(2) 0.0423(8) Uani 1 1 d . . C19 C 0.2834(3) 0.5040(3) 0.0090(2) 0.0458(8) Uani 1 1 d . . H19A H 0.340930 0.502605 0.061110 0.055 Uiso 1 1 calc R U C20 C 0.2177(3) 0.5826(3) -0.0144(2) 0.0418(8) Uani 1 1 d . . C21 C 0.0859(5) 0.6975(4) -0.2113(3) 0.0764(14) Uani 1 1 d . . H21A H 0.039177 0.749915 -0.231773 0.115 Uiso 1 1 calc R U H21B H 0.171743 0.710935 -0.203688 0.115 Uiso 1 1 calc R U H21C H 0.066062 0.650149 -0.253605 0.115 Uiso 1 1 calc R U C22 C -0.0818(4) 0.6443(4) -0.1359(4) 0.0822(15) Uani 1 1 d . . H22A H -0.129571 0.696623 -0.155271 0.123 Uiso 1 1 calc R U H22B H -0.100452 0.597944 -0.179384 0.123 Uiso 1 1 calc R U H22C H -0.100819 0.623798 -0.081224 0.123 Uiso 1 1 calc R U C23 C 0.2654(5) 0.3517(4) -0.2399(3) 0.0730(13) Uani 1 1 d . . H23A H 0.252218 0.403954 -0.276596 0.110 Uiso 1 1 calc R U H23B H 0.344896 0.354951 -0.202770 0.110 Uiso 1 1 calc R U H23C H 0.260689 0.299080 -0.276067 0.110 Uiso 1 1 calc R U C24 C 0.0408(5) 0.3441(5) -0.2426(4) 0.096(2) Uani 1 1 d . . H24A H 0.028295 0.398355 -0.276509 0.144 Uiso 1 1 calc R U H24B H 0.037048 0.293691 -0.281574 0.144 Uiso 1 1 calc R U H24C H -0.021737 0.338544 -0.207823 0.144 Uiso 1 1 calc R U C25 C 0.3171(3) 0.6485(3) 0.1255(2) 0.0440(8) Uani 1 1 d . . C26 C 0.4420(3) 0.6497(3) 0.1335(2) 0.0535(10) Uani 1 1 d . . H26A H 0.476035 0.657349 0.083536 0.064 Uiso 1 1 calc R U C27 C 0.5181(3) 0.6399(3) 0.2142(2) 0.0558(10) Uani 1 1 d . . H27A H 0.602601 0.640682 0.218148 0.067 Uiso 1 1 calc R U C28 C 0.4689(3) 0.6289(3) 0.2901(2) 0.0471(8) Uani 1 1 d . . C29 C 0.3430(3) 0.6286(3) 0.2816(2) 0.0550(10) Uani 1 1 d . . H29A H 0.308537 0.622456 0.331603 0.066 Uiso 1 1 calc R U C30 C 0.2671(3) 0.6373(3) 0.2004(2) 0.0549(10) Uani 1 1 d . . H30A H 0.182571 0.635766 0.195992 0.066 Uiso 1 1 calc R U C31 C 0.5507(3) 0.6238(3) 0.3773(2) 0.0479(9) Uani 1 1 d . . C32 C 0.7411(3) 0.6347(3) 0.4593(2) 0.0474(8) Uani 1 1 d . . C33 C 0.5776(3) 0.6187(3) 0.5257(2) 0.0505(9) Uani 1 1 d . . C34 C 0.8745(3) 0.6459(3) 0.4647(2) 0.0498(9) Uani 1 1 d . . C35 C 0.9501(4) 0.6692(4) 0.5436(3) 0.0670(13) Uani 1 1 d . . H35A H 0.917674 0.674733 0.594568 0.080 Uiso 1 1 calc R U C36 C 1.0732(4) 0.6842(4) 0.5465(3) 0.0720(13) Uani 1 1 d . . H36A H 1.123339 0.700312 0.599289 0.086 Uiso 1 1 calc R U C37 C 1.1224(4) 0.6755(4) 0.4716(3) 0.0644(12) Uani 1 1 d . . H37A H 1.205158 0.686660 0.473645 0.077 Uiso 1 1 calc R U C38 C 1.0491(4) 0.6505(3) 0.3945(3) 0.0621(11) Uani 1 1 d . . H38A H 1.082725 0.643159 0.344213 0.075 Uiso 1 1 calc R U C39 C 0.9253(3) 0.6358(3) 0.3904(2) 0.0567(10) Uani 1 1 d . . H39A H 0.876107 0.619121 0.337359 0.068 Uiso 1 1 calc R U C40 C 0.5274(4) 0.6107(3) 0.6081(2) 0.0526(9) Uani 1 1 d . . C41 C 0.6036(5) 0.6199(4) 0.6890(3) 0.0748(15) Uani 1 1 d . . H41A H 0.686275 0.632064 0.691841 0.090 Uiso 1 1 calc R U C42 C 0.5587(6) 0.6113(5) 0.7652(3) 0.0902(19) Uani 1 1 d . . H42A H 0.611153 0.617236 0.819264 0.108 Uiso 1 1 calc R U C43 C 0.4367(6) 0.5939(4) 0.7622(3) 0.0839(16) Uani 1 1 d . . H43A H 0.406431 0.588244 0.813999 0.101 Uiso 1 1 calc R U C44 C 0.3606(5) 0.5849(4) 0.6829(3) 0.0808(15) Uani 1 1 d . . H44A H 0.277788 0.573514 0.680702 0.097 Uiso 1 1 calc R U C45 C 0.4050(4) 0.5925(4) 0.6053(3) 0.0678(12) Uani 1 1 d . . H45A H 0.352419 0.585424 0.551426 0.081 Uiso 1 1 calc R U C46 C 0.4206(3) 0.3515(3) 0.0633(2) 0.0448(8) Uani 1 1 d . . C47 C 0.5431(3) 0.3661(3) 0.0622(2) 0.0533(10) Uani 1 1 d . . H47A H 0.569892 0.370250 0.008947 0.064 Uiso 1 1 calc R U C48 C 0.6251(3) 0.3745(3) 0.1401(2) 0.0566(11) Uani 1 1 d . . H48A H 0.707466 0.384014 0.139026 0.068 Uiso 1 1 calc R U C49 C 0.5870(3) 0.3691(3) 0.2206(2) 0.0482(9) Uani 1 1 d . . C50 C 0.4644(3) 0.3526(3) 0.2204(2) 0.0555(10) Uani 1 1 d . . H50A H 0.437474 0.347577 0.273603 0.067 Uiso 1 1 calc R U C51 C 0.3819(3) 0.3435(3) 0.1426(2) 0.0553(10) Uani 1 1 d . . H51A H 0.299944 0.331870 0.143511 0.066 Uiso 1 1 calc R U C52 C 0.6739(3) 0.3815(3) 0.3047(2) 0.0475(9) Uani 1 1 d . . C53 C 0.8667(3) 0.4046(3) 0.3798(2) 0.0503(9) Uani 1 1 d . . C54 C 0.7101(3) 0.3892(3) 0.4531(2) 0.0498(9) Uani 1 1 d . . C55 C 0.9993(3) 0.4144(3) 0.3814(3) 0.0538(9) Uani 1 1 d . . C56 C 1.0819(4) 0.4117(4) 0.4609(3) 0.0696(13) Uani 1 1 d . . H56A H 1.053754 0.404725 0.513404 0.084 Uiso 1 1 calc R U C57 C 1.2058(4) 0.4193(5) 0.4615(4) 0.0845(16) Uani 1 1 d . . H57A H 1.261093 0.417107 0.514645 0.101 Uiso 1 1 calc R U C58 C 1.2480(4) 0.4301(5) 0.3846(4) 0.0837(16) Uani 1 1 d . . H58A H 1.331665 0.435255 0.385714 0.100 Uiso 1 1 calc R U C59 C 1.1677(4) 0.4333(4) 0.3063(3) 0.0742(14) Uani 1 1 d . . H59A H 1.196872 0.440897 0.254222 0.089 Uiso 1 1 calc R U C60 C 1.0437(4) 0.4253(3) 0.3039(3) 0.0616(11) Uani 1 1 d . . H60A H 0.989506 0.427144 0.250257 0.074 Uiso 1 1 calc R U C61 C 0.6658(3) 0.3838(3) 0.5376(2) 0.0524(9) Uani 1 1 d . . C62 C 0.7418(4) 0.4054(4) 0.6154(3) 0.0746(15) Uani 1 1 d . . H62A H 0.821590 0.424106 0.615148 0.090 Uiso 1 1 calc R U C63 C 0.7007(5) 0.3995(5) 0.6941(3) 0.0871(18) Uani 1 1 d . . H63A H 0.753013 0.414257 0.746415 0.104 Uiso 1 1 calc R U C64 C 0.5837(4) 0.3722(4) 0.6955(3) 0.0723(14) Uani 1 1 d . . H64A H 0.556445 0.368714 0.748705 0.087 Uiso 1 1 calc R U C65 C 0.5075(4) 0.3503(4) 0.6193(3) 0.0680(12) Uani 1 1 d . . H65A H 0.427898 0.331828 0.620405 0.082 Uiso 1 1 calc R U C66 C 0.5471(4) 0.3551(4) 0.5401(3) 0.0607(10) Uani 1 1 d . . H66A H 0.494490 0.339243 0.488259 0.073 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 N1 0.0501(16) 0.050(2) 0.0376(14) -0.0064(13) -0.0024(12) 0.0032(14) N2 0.0419(14) 0.0483(18) 0.0462(14) -0.0083(14) -0.0021(12) 0.0061(14) N3 0.0448(16) 0.068(2) 0.0404(14) -0.0028(15) 0.0006(12) -0.0023(16) N4 0.0494(17) 0.069(2) 0.0389(14) 0.0032(15) -0.0006(12) -0.0026(16) N5 0.0495(16) 0.062(2) 0.0411(15) 0.0026(14) 0.0032(13) -0.0022(15) N6 0.0410(15) 0.063(2) 0.0485(15) -0.0025(15) 0.0036(12) 0.0000(15) N7 0.0438(16) 0.074(3) 0.0483(16) -0.0002(17) 0.0020(13) 0.0002(17) N8 0.0427(15) 0.069(2) 0.0453(15) 0.0019(15) 0.0024(13) 0.0004(15) C1 0.0467(18) 0.053(2) 0.0375(16) 0.0005(15) 0.0105(14) 0.0021(17) C2 0.078(3) 0.058(3) 0.045(2) -0.0060(18) 0.0039(19) 0.009(2) C3 0.104(3) 0.054(3) 0.057(2) -0.005(2) 0.014(2) 0.007(3) C4 0.093(3) 0.060(3) 0.057(2) 0.005(2) 0.017(2) 0.024(3) C5 0.061(2) 0.066(3) 0.0459(19) 0.0095(19) 0.0099(17) 0.017(2) C6 0.0456(18) 0.053(2) 0.0380(16) 0.0055(15) 0.0121(14) 0.0044(16) C7 0.0431(18) 0.053(2) 0.0411(17) 0.0031(15) 0.0030(14) 0.0019(16) C8 0.0388(16) 0.049(2) 0.0344(15) -0.0011(15) 0.0045(13) 0.0022(15) C9 0.0411(17) 0.060(3) 0.0335(15) -0.0055(16) -0.0039(13) 0.0008(17) C10 0.0376(16) 0.055(2) 0.0383(16) -0.0070(16) 0.0001(13) 0.0026(16) C11 0.0496(19) 0.066(3) 0.0400(16) -0.0120(18) 0.0005(15) 0.002(2) C12 0.0501(19) 0.059(3) 0.0423(17) -0.0113(17) 0.0146(15) -0.0057(18) C13 0.078(3) 0.071(3) 0.054(2) -0.015(2) 0.015(2) -0.026(3) C14 0.130(5) 0.065(3) 0.067(3) -0.011(3) 0.027(3) -0.032(3) C15 0.129(5) 0.051(3) 0.061(3) 0.000(2) 0.029(3) -0.012(3) C16 0.074(3) 0.058(3) 0.0461(19) -0.0009(19) 0.0162(18) 0.004(2) C17 0.0468(18) 0.050(2) 0.0441(17) -0.0091(17) 0.0149(15) -0.0024(18) C18 0.0370(16) 0.049(2) 0.0398(16) -0.0065(15) 0.0035(13) 0.0017(15) C19 0.0393(16) 0.053(2) 0.0399(17) -0.0059(16) -0.0047(13) 0.0053(17) C20 0.0377(16) 0.051(2) 0.0351(15) -0.0034(15) 0.0032(13) 0.0017(16) C21 0.123(4) 0.066(3) 0.0389(19) 0.004(2) 0.014(2) 0.012(3) C22 0.041(2) 0.064(3) 0.133(4) -0.008(3) -0.005(2) 0.006(2) C23 0.109(4) 0.063(3) 0.055(2) -0.002(2) 0.035(2) 0.006(3) C24 0.083(3) 0.094(4) 0.092(3) -0.046(3) -0.035(3) 0.020(3) C25 0.0477(18) 0.045(2) 0.0353(15) -0.0063(15) -0.0017(13) -0.0006(17) C26 0.0469(19) 0.077(3) 0.0360(16) -0.0057(17) 0.0057(14) -0.007(2) C27 0.0398(18) 0.082(3) 0.0443(18) -0.003(2) 0.0038(15) -0.007(2) C28 0.0440(18) 0.058(2) 0.0366(16) -0.0037(16) -0.0003(14) -0.0064(17) C29 0.0450(19) 0.080(3) 0.0395(17) 0.0030(19) 0.0072(14) -0.003(2) C30 0.0377(17) 0.080(3) 0.0446(18) -0.001(2) 0.0026(14) -0.0025(19) C31 0.0448(18) 0.057(3) 0.0390(16) -0.0010(16) 0.0013(14) -0.0021(17) C32 0.0467(19) 0.051(2) 0.0412(16) 0.0031(17) -0.0010(14) -0.0025(17) C33 0.049(2) 0.059(3) 0.0414(17) 0.0008(17) 0.0038(15) -0.0021(18) C34 0.0442(18) 0.056(3) 0.0451(18) 0.0052(17) -0.0010(15) -0.0010(18) C35 0.052(2) 0.098(4) 0.047(2) -0.004(2) -0.0004(17) -0.006(2) C36 0.052(2) 0.098(4) 0.058(2) -0.001(2) -0.0093(19) -0.011(2) C37 0.0430(19) 0.076(3) 0.071(3) 0.012(2) 0.0025(19) -0.003(2) C38 0.050(2) 0.077(3) 0.058(2) 0.011(2) 0.0080(17) 0.003(2) C39 0.048(2) 0.075(3) 0.0433(18) 0.0085(19) -0.0013(15) -0.001(2) C40 0.056(2) 0.059(3) 0.0424(17) 0.0002(17) 0.0072(16) 0.0030(18) C41 0.072(3) 0.105(4) 0.046(2) -0.007(2) 0.0063(19) -0.009(3) C42 0.104(4) 0.123(6) 0.044(2) -0.009(3) 0.014(2) -0.002(4) C43 0.106(4) 0.095(4) 0.058(3) 0.004(3) 0.035(3) 0.013(3) C44 0.072(3) 0.099(4) 0.078(3) 0.021(3) 0.029(2) 0.014(3) C45 0.062(2) 0.084(4) 0.057(2) 0.014(2) 0.0111(19) 0.004(2) C46 0.0371(16) 0.050(2) 0.0439(16) -0.0027(17) -0.0007(13) 0.0076(16) C47 0.0427(18) 0.074(3) 0.0421(17) 0.0021(18) 0.0048(14) 0.0020(18) C48 0.0356(16) 0.080(3) 0.053(2) 0.006(2) 0.0050(15) 0.0006(18) C49 0.0385(16) 0.056(3) 0.0474(17) -0.0001(16) 0.0022(14) 0.0040(16) C50 0.0415(18) 0.079(3) 0.0463(18) -0.003(2) 0.0077(15) 0.003(2) C51 0.0352(16) 0.078(3) 0.0517(19) -0.006(2) 0.0047(14) -0.0002(19) C52 0.0397(17) 0.055(2) 0.0454(17) 0.0014(16) 0.0022(14) 0.0034(17) C53 0.0409(17) 0.059(3) 0.0488(18) -0.0001(18) 0.0025(15) -0.0002(18) C54 0.0441(18) 0.056(2) 0.0463(18) 0.0021(18) 0.0007(15) 0.0033(18) C55 0.0424(18) 0.058(3) 0.058(2) -0.0043(19) 0.0020(16) -0.0005(18) C56 0.046(2) 0.090(4) 0.068(2) 0.007(2) -0.0004(18) -0.005(2) C57 0.045(2) 0.110(5) 0.090(3) 0.002(3) -0.008(2) -0.006(3) C58 0.041(2) 0.103(4) 0.107(4) -0.006(3) 0.011(2) -0.010(2) C59 0.053(2) 0.092(4) 0.080(3) -0.014(3) 0.019(2) -0.009(2) C60 0.049(2) 0.072(3) 0.063(2) -0.005(2) 0.0081(17) -0.003(2) C61 0.0470(18) 0.065(3) 0.0435(17) 0.0064(18) 0.0042(15) 0.0075(18) C62 0.053(2) 0.121(5) 0.048(2) 0.005(3) 0.0054(17) -0.002(3) C63 0.075(3) 0.137(6) 0.046(2) 0.002(3) 0.004(2) 0.001(3) C64 0.072(3) 0.093(4) 0.055(2) 0.018(2) 0.020(2) 0.016(3) C65 0.059(2) 0.077(3) 0.069(3) 0.015(2) 0.018(2) 0.005(2) C66 0.052(2) 0.071(3) 0.058(2) 0.003(2) 0.0074(17) 0.002(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _citation_id _citation_doi _citation_year 1 10.1039/C9CC08679J 2019 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C20 121.1(3) C1 N1 C25 119.7(3) C20 N1 C25 118.9(3) C17 N2 C18 119.0(3) C17 N2 C46 119.3(3) C18 N2 C46 116.8(3) C32 N3 C31 115.7(3) C33 N4 C32 115.9(3) C33 N5 C31 114.7(3) C53 N6 C52 115.3(3) C54 N7 C53 115.7(3) C52 N8 C54 115.3(3) N1 C1 C2 120.2(3) N1 C1 C6 120.9(3) C2 C1 C6 118.9(4) C3 C2 C1 121.2(4) C3 C2 H2A 119.4 C1 C2 H2A 119.4 C2 C3 C4 120.7(5) C2 C3 H3B 119.6 C4 C3 H3B 119.6 C5 C4 C3 118.6(4) C5 C4 H4B 120.7 C3 C4 H4B 120.7 C4 C5 C6 123.0(4) C4 C5 H5B 118.5 C6 C5 H5B 118.5 C1 C6 C5 117.4(4) C1 C6 C7 122.4(3) C5 C6 C7 120.1(3) C8 C7 C6 111.7(3) C8 C7 C21 108.2(3) C6 C7 C21 108.6(3) C8 C7 C22 109.3(3) C6 C7 C22 109.9(3) C21 C7 C22 109.2(4) C9 C8 C20 117.1(3) C9 C8 C7 120.1(3) C20 C8 C7 122.7(3) C10 C9 C8 125.2(3) C10 C9 H9A 117.4 C8 C9 H9A 117.4 C9 C10 C18 116.4(3) C9 C10 C11 123.4(3) C18 C10 C11 120.0(3) C12 C11 C10 108.8(3) C12 C11 C24 112.6(4) C10 C11 C24 111.7(4) C12 C11 C23 106.5(3) C10 C11 C23 108.7(4) C24 C11 C23 108.4(4) C13 C12 C17 116.9(4) C13 C12 C11 123.1(4) C17 C12 C11 119.7(4) C14 C13 C12 122.8(4) C14 C13 H13A 118.6 C12 C13 H13A 118.6 C13 C14 C15 119.5(5) C13 C14 H14A 120.3 C15 C14 H14A 120.3 C14 C15 C16 120.1(5) C14 C15 H15A 119.9 C16 C15 H15A 119.9 C15 C16 C17 120.5(4) C15 C16 H16A 119.7 C17 C16 H16A 119.7 C16 C17 N2 120.8(3) C16 C17 C12 120.1(4) N2 C17 C12 119.1(4) C19 C18 C10 120.1(3) C19 C18 N2 120.8(3) C10 C18 N2 119.1(3) C18 C19 C20 121.8(3) C18 C19 H19A 119.1 C20 C19 H19A 119.1 C19 C20 C8 119.3(3) C19 C20 N1 119.7(3) C8 C20 N1 121.0(3) C7 C21 H21A 109.5 C7 C21 H21B 109.5 H21A C21 H21B 109.5 C7 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C7 C22 H22A 109.5 C7 C22 H22B 109.5 H22A C22 H22B 109.5 C7 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 C11 C23 H23A 109.5 C11 C23 H23B 109.5 H23A C23 H23B 109.5 C11 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 C11 C24 H24A 109.5 C11 C24 H24B 109.5 H24A C24 H24B 109.5 C11 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 C26 C25 C30 119.0(3) C26 C25 N1 120.9(3) C30 C25 N1 120.1(3) C25 C26 C27 121.3(3) C25 C26 H26A 119.4 C27 C26 H26A 119.4 C26 C27 C28 120.3(3) C26 C27 H27A 119.9 C28 C27 H27A 119.9 C29 C28 C27 118.1(3) C29 C28 C31 121.6(3) C27 C28 C31 120.2(3) C30 C29 C28 121.4(3) C30 C29 H29A 119.3 C28 C29 H29A 119.3 C29 C30 C25 120.0(3) C29 C30 H30A 120.0 C25 C30 H30A 120.0 N3 C31 N5 124.6(3) N3 C31 C28 117.3(3) N5 C31 C28 118.1(3) N3 C32 N4 124.1(3) N3 C32 C34 117.4(3) N4 C32 C34 118.4(3) N4 C33 N5 124.9(3) N4 C33 C40 117.2(3) N5 C33 C40 118.0(3) C39 C34 C35 119.0(4) C39 C34 C32 120.3(3) C35 C34 C32 120.7(3) C36 C35 C34 120.0(4) C36 C35 H35A 120.0 C34 C35 H35A 120.0 C37 C36 C35 120.5(4) C37 C36 H36A 119.8 C35 C36 H36A 119.8 C38 C37 C36 119.7(4) C38 C37 H37A 120.1 C36 C37 H37A 120.1 C37 C38 C39 120.5(4) C37 C38 H38A 119.7 C39 C38 H38A 119.7 C34 C39 C38 120.2(4) C34 C39 H39A 119.9 C38 C39 H39A 119.9 C41 C40 C45 118.7(4) C41 C40 C33 120.3(4) C45 C40 C33 121.0(3) C42 C41 C40 120.7(5) C42 C41 H41A 119.6 C40 C41 H41A 119.6 C41 C42 C43 120.4(5) C41 C42 H42A 119.8 C43 C42 H42A 119.8 C44 C43 C42 119.5(4) C44 C43 H43A 120.2 C42 C43 H43A 120.2 C43 C44 C45 120.7(5) C43 C44 H44A 119.7 C45 C44 H44A 119.7 C40 C45 C44 120.0(4) C40 C45 H45A 120.0 C44 C45 H45A 120.0 C51 C46 C47 119.8(3) C51 C46 N2 120.2(3) C47 C46 N2 119.9(3) C48 C47 C46 119.8(3) C48 C47 H47A 120.1 C46 C47 H47A 120.1 C47 C48 C49 121.1(3) C47 C48 H48A 119.4 C49 C48 H48A 119.4 C50 C49 C48 118.3(3) C50 C49 C52 120.2(3) C48 C49 C52 121.5(3) C51 C50 C49 120.9(3) C51 C50 H50A 119.6 C49 C50 H50A 119.6 C50 C51 C46 120.1(3) C50 C51 H51A 120.0 C46 C51 H51A 120.0 N8 C52 N6 124.7(3) N8 C52 C49 117.3(3) N6 C52 C49 118.0(3) N6 C53 N7 124.2(3) N6 C53 C55 118.1(3) N7 C53 C55 117.6(3) N7 C54 N8 124.7(3) N7 C54 C61 117.3(3) N8 C54 C61 118.0(3) C60 C55 C56 119.0(4) C60 C55 C53 120.9(3) C56 C55 C53 120.2(4) C57 C56 C55 119.7(4) C57 C56 H56A 120.1 C55 C56 H56A 120.1 C58 C57 C56 120.6(5) C58 C57 H57A 119.7 C56 C57 H57A 119.7 C59 C58 C57 120.2(4) C59 C58 H58A 119.9 C57 C58 H58A 119.9 C58 C59 C60 120.3(5) C58 C59 H59A 119.8 C60 C59 H59A 119.8 C59 C60 C55 120.3(4) C59 C60 H60A 119.9 C55 C60 H60A 119.9 C62 C61 C66 118.5(4) C62 C61 C54 120.6(4) C66 C61 C54 120.9(3) C61 C62 C63 120.4(4) C61 C62 H62A 119.8 C63 C62 H62A 119.8 C64 C63 C62 120.5(4) C64 C63 H63A 119.8 C62 C63 H63A 119.8 C65 C64 C63 119.8(4) C65 C64 H64A 120.1 C63 C64 H64A 120.1 C64 C65 C66 120.5(4) C64 C65 H65A 119.7 C66 C65 H65A 119.7 C65 C66 C61 120.2(4) C65 C66 H66A 119.9 C61 C66 H66A 119.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C1 1.399(5) N1 C20 1.400(5) N1 C25 1.438(4) N2 C17 1.405(5) N2 C18 1.419(5) N2 C46 1.437(4) N3 C32 1.334(4) N3 C31 1.336(5) N4 C33 1.332(5) N4 C32 1.336(5) N5 C33 1.336(5) N5 C31 1.348(5) N6 C53 1.340(5) N6 C52 1.340(5) N7 C54 1.331(5) N7 C53 1.340(5) N8 C52 1.334(5) N8 C54 1.337(4) C1 C2 1.401(6) C1 C6 1.402(5) C2 C3 1.371(7) C2 H2A 0.9300 C3 C4 1.372(7) C3 H3B 0.9300 C4 C5 1.367(7) C4 H4B 0.9300 C5 C6 1.407(6) C5 H5B 0.9300 C6 C7 1.521(5) C7 C8 1.517(5) C7 C21 1.537(5) C7 C22 1.539(5) C8 C9 1.388(5) C8 C20 1.397(4) C9 C10 1.385(6) C9 H9A 0.9300 C10 C18 1.397(5) C10 C11 1.521(6) C11 C12 1.514(6) C11 C24 1.527(6) C11 C23 1.545(6) C12 C13 1.400(6) C12 C17 1.407(5) C13 C14 1.374(8) C13 H13A 0.9300 C14 C15 1.375(8) C14 H14A 0.9300 C15 C16 1.382(7) C15 H15A 0.9300 C16 C17 1.400(6) C16 H16A 0.9300 C18 C19 1.389(5) C19 C20 1.393(5) C19 H19A 0.9300 C21 H21A 0.9600 C21 H21B 0.9600 C21 H21C 0.9600 C22 H22A 0.9600 C22 H22B 0.9600 C22 H22C 0.9600 C23 H23A 0.9600 C23 H23B 0.9600 C23 H23C 0.9600 C24 H24A 0.9600 C24 H24B 0.9600 C24 H24C 0.9600 C25 C26 1.371(5) C25 C30 1.386(5) C26 C27 1.378(5) C26 H26A 0.9300 C27 C28 1.395(5) C27 H27A 0.9300 C28 C29 1.381(5) C28 C31 1.479(5) C29 C30 1.381(5) C29 H29A 0.9300 C30 H30A 0.9300 C32 C34 1.480(5) C33 C40 1.490(5) C34 C39 1.381(6) C34 C35 1.390(5) C35 C36 1.379(6) C35 H35A 0.9300 C36 C37 1.376(7) C36 H36A 0.9300 C37 C38 1.365(6) C37 H37A 0.9300 C38 C39 1.383(6) C38 H38A 0.9300 C39 H39A 0.9300 C40 C41 1.380(6) C40 C45 1.380(6) C41 C42 1.370(7) C41 H41A 0.9300 C42 C43 1.372(8) C42 H42A 0.9300 C43 C44 1.359(8) C43 H43A 0.9300 C44 C45 1.386(7) C44 H44A 0.9300 C45 H45A 0.9300 C46 C51 1.379(5) C46 C47 1.383(5) C47 C48 1.373(5) C47 H47A 0.9300 C48 C49 1.391(5) C48 H48A 0.9300 C49 C50 1.385(5) C49 C52 1.479(5) C50 C51 1.376(5) C50 H50A 0.9300 C51 H51A 0.9300 C53 C55 1.477(5) C54 C61 1.483(5) C55 C60 1.388(6) C55 C56 1.390(6) C56 C57 1.381(6) C56 H56A 0.9300 C57 C58 1.368(8) C57 H57A 0.9300 C58 C59 1.363(7) C58 H58A 0.9300 C59 C60 1.378(6) C59 H59A 0.9300 C60 H60A 0.9300 C61 C62 1.373(6) C61 C66 1.395(6) C62 C63 1.381(7) C62 H62A 0.9300 C63 C64 1.367(7) C63 H63A 0.9300 C64 C65 1.357(7) C64 H64A 0.9300 C65 C66 1.379(6) C65 H65A 0.9300 C66 H66A 0.9300 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 C20 N1 C1 C2 -176.3(3) C25 N1 C1 C2 9.8(5) C20 N1 C1 C6 3.3(5) C25 N1 C1 C6 -170.7(3) N1 C1 C2 C3 -178.5(4) C6 C1 C2 C3 2.0(6) C1 C2 C3 C4 0.7(8) C2 C3 C4 C5 -2.6(7) C3 C4 C5 C6 1.9(7) N1 C1 C6 C5 177.8(3) C2 C1 C6 C5 -2.7(5) N1 C1 C6 C7 -3.9(5) C2 C1 C6 C7 175.6(4) C4 C5 C6 C1 0.8(6) C4 C5 C6 C7 -177.6(4) C1 C6 C7 C8 3.0(5) C5 C6 C7 C8 -178.7(3) C1 C6 C7 C21 -116.2(4) C5 C6 C7 C21 62.0(5) C1 C6 C7 C22 124.5(4) C5 C6 C7 C22 -57.3(5) C6 C7 C8 C9 179.4(3) C21 C7 C8 C9 -61.1(4) C22 C7 C8 C9 57.6(5) C6 C7 C8 C20 -1.8(5) C21 C7 C8 C20 117.7(4) C22 C7 C8 C20 -123.5(4) C20 C8 C9 C10 0.7(5) C7 C8 C9 C10 179.6(3) C8 C9 C10 C18 -0.2(5) C8 C9 C10 C11 -176.0(3) C9 C10 C11 C12 -151.6(4) C18 C10 C11 C12 32.7(4) C9 C10 C11 C24 -26.7(6) C18 C10 C11 C24 157.6(4) C9 C10 C11 C23 92.9(4) C18 C10 C11 C23 -82.8(4) C10 C11 C12 C13 151.8(4) C24 C11 C12 C13 27.4(5) C23 C11 C12 C13 -91.3(5) C10 C11 C12 C17 -35.7(4) C24 C11 C12 C17 -160.1(4) C23 C11 C12 C17 81.2(4) C17 C12 C13 C14 -4.0(6) C11 C12 C13 C14 168.7(4) C12 C13 C14 C15 0.4(8) C13 C14 C15 C16 2.3(8) C14 C15 C16 C17 -1.2(7) C15 C16 C17 N2 179.1(4) C15 C16 C17 C12 -2.5(6) C18 N2 C17 C16 -159.7(3) C46 N2 C17 C16 -5.1(5) C18 N2 C17 C12 21.9(5) C46 N2 C17 C12 176.5(3) C13 C12 C17 C16 4.9(5) C11 C12 C17 C16 -168.0(3) C13 C12 C17 N2 -176.6(3) C11 C12 C17 N2 10.4(5) C9 C10 C18 C19 -0.2(5) C11 C10 C18 C19 175.8(3) C9 C10 C18 N2 179.5(3) C11 C10 C18 N2 -4.5(5) C17 N2 C18 C19 154.7(3) C46 N2 C18 C19 -0.5(5) C17 N2 C18 C10 -24.9(5) C46 N2 C18 C10 179.9(3) C10 C18 C19 C20 0.0(5) N2 C18 C19 C20 -179.7(3) C18 C19 C20 C8 0.5(5) C18 C19 C20 N1 179.5(3) C9 C8 C20 C19 -0.8(5) C7 C8 C20 C19 -179.7(3) C9 C8 C20 N1 -179.7(3) C7 C8 C20 N1 1.4(5) C1 N1 C20 C19 179.1(3) C25 N1 C20 C19 -6.9(5) C1 N1 C20 C8 -2.0(5) C25 N1 C20 C8 172.0(3) C1 N1 C25 C26 -106.3(4) C20 N1 C25 C26 79.6(5) C1 N1 C25 C30 74.4(5) C20 N1 C25 C30 -99.7(4) C30 C25 C26 C27 0.2(7) N1 C25 C26 C27 -179.1(4) C25 C26 C27 C28 -0.3(7) C26 C27 C28 C29 -0.4(7) C26 C27 C28 C31 -176.3(4) C27 C28 C29 C30 1.2(7) C31 C28 C29 C30 177.1(4) C28 C29 C30 C25 -1.3(8) C26 C25 C30 C29 0.6(7) N1 C25 C30 C29 179.9(4) C32 N3 C31 N5 -3.3(6) C32 N3 C31 C28 174.0(4) C33 N5 C31 N3 2.5(6) C33 N5 C31 C28 -174.8(4) C29 C28 C31 N3 -175.1(4) C27 C28 C31 N3 0.7(6) C29 C28 C31 N5 2.4(6) C27 C28 C31 N5 178.2(4) C31 N3 C32 N4 0.6(7) C31 N3 C32 C34 -178.0(4) C33 N4 C32 N3 2.7(7) C33 N4 C32 C34 -178.8(4) C32 N4 C33 N5 -3.6(6) C32 N4 C33 C40 178.0(4) C31 N5 C33 N4 1.2(6) C31 N5 C33 C40 179.6(4) N3 C32 C34 C39 -12.0(6) N4 C32 C34 C39 169.3(4) N3 C32 C34 C35 166.1(5) N4 C32 C34 C35 -12.5(6) C39 C34 C35 C36 1.7(8) C32 C34 C35 C36 -176.5(5) C34 C35 C36 C37 -0.6(8) C35 C36 C37 C38 -1.1(8) C36 C37 C38 C39 1.6(8) C35 C34 C39 C38 -1.2(7) C32 C34 C39 C38 177.0(4) C37 C38 C39 C34 -0.4(8) N4 C33 C40 C41 3.1(7) N5 C33 C40 C41 -175.4(4) N4 C33 C40 C45 -175.7(4) N5 C33 C40 C45 5.7(6) C45 C40 C41 C42 -0.1(8) C33 C40 C41 C42 -179.0(5) C40 C41 C42 C43 -0.4(10) C41 C42 C43 C44 0.2(10) C42 C43 C44 C45 0.4(10) C41 C40 C45 C44 0.7(8) C33 C40 C45 C44 179.6(5) C43 C44 C45 C40 -0.9(9) C17 N2 C46 C51 -76.0(5) C18 N2 C46 C51 79.1(5) C17 N2 C46 C47 106.6(4) C18 N2 C46 C47 -98.3(4) C51 C46 C47 C48 -1.4(7) N2 C46 C47 C48 176.0(4) C46 C47 C48 C49 -0.4(7) C47 C48 C49 C50 1.7(7) C47 C48 C49 C52 -177.7(4) C48 C49 C50 C51 -1.2(7) C52 C49 C50 C51 178.2(4) C49 C50 C51 C46 -0.5(8) C47 C46 C51 C50 1.9(7) N2 C46 C51 C50 -175.5(4) C54 N8 C52 N6 1.1(6) C54 N8 C52 C49 -179.8(4) C53 N6 C52 N8 -0.3(6) C53 N6 C52 C49 -179.4(4) C50 C49 C52 N8 -1.1(6) C48 C49 C52 N8 178.2(4) C50 C49 C52 N6 178.0(4) C48 C49 C52 N6 -2.6(6) C52 N6 C53 N7 -1.0(6) C52 N6 C53 C55 176.7(4) C54 N7 C53 N6 1.4(7) C54 N7 C53 C55 -176.3(4) C53 N7 C54 N8 -0.6(7) C53 N7 C54 C61 177.7(4) C52 N8 C54 N7 -0.6(6) C52 N8 C54 C61 -178.8(4) N6 C53 C55 C60 8.6(7) N7 C53 C55 C60 -173.5(4) N6 C53 C55 C56 -170.5(4) N7 C53 C55 C56 7.4(7) C60 C55 C56 C57 -0.3(8) C53 C55 C56 C57 178.8(5) C55 C56 C57 C58 0.4(10) C56 C57 C58 C59 -0.1(10) C57 C58 C59 C60 -0.3(10) C58 C59 C60 C55 0.4(8) C56 C55 C60 C59 -0.1(7) C53 C55 C60 C59 -179.2(5) N7 C54 C61 C62 9.1(7) N8 C54 C61 C62 -172.5(5) N7 C54 C61 C66 -169.6(4) N8 C54 C61 C66 8.8(6) C66 C61 C62 C63 -0.6(9) C54 C61 C62 C63 -179.4(5) C61 C62 C63 C64 -0.1(10) C62 C63 C64 C65 0.3(10) C63 C64 C65 C66 0.1(9) C64 C65 C66 C61 -0.8(8) C62 C61 C66 C65 1.1(8) C54 C61 C66 C65 179.8(5)