#------------------------------------------------------------------------------ #$Date: 2015-09-26 10:42:15 +0300 (Sat, 26 Sep 2015) $ #$Revision: 158423 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/23/7222304.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_7222304 loop_ _publ_author_name 'Kwit, Marcin' 'Rychlewska, Urszula' 'Prusinowska, Natalia' 'Bendzi\'nska-Berus, Wioletta' 'War\.zajtis, Beata' 'Gajewy, Jadwiga' 'Szymkowiak, Joanna' 'Jelecki, Maciej' _publ_section_title ; Double helicity induction in chiral bis(triphenylacetamides) ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C5RA15554A _journal_year 2015 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C48 H46 N2 O2, C H2 Cl2' _chemical_formula_sum 'C49 H48 Cl2 N2 O2' _chemical_formula_weight 767.79 _chemical_name_systematic ; ? ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _audit_update_record ; 2015-07-23 deposited with the CCDC. 2015-09-25 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.4884(2) _cell_length_b 19.7670(3) _cell_length_c 20.3090(3) _cell_measurement_reflns_used 45213 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 76.3081 _cell_measurement_theta_min 2.1740 _cell_volume 4210.55(12) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies (2013) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies (2013) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies (2013) ; _computing_molecular_graphics ; Mercury (Bruno, et al. 2002) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 2008)' _diffrn_ambient_temperature 295(2) _diffrn_detector_area_resol_mean 10.5357 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'SuperNova, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 53532 _diffrn_reflns_theta_full 76.48 _diffrn_reflns_theta_max 76.48 _diffrn_reflns_theta_min 3.12 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 50 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 1.698 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.87392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro (Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, Agilent Technologies 2013) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1624 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.309 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_extinction_coef 0.0021(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 527 _refine_ls_number_reflns 8783 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0449 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0929P)^2^+0.4825P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1355 _refine_ls_wR_factor_ref 0.1362 _reflns_number_gt 8690 _reflns_number_total 8783 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL chnmeap in P2(1)2(1)2(1) CELL 1.54178 10.4884 19.7670 20.3090 90.000 90.000 90.000 ZERR 4.00 0.0002 0.0003 0.0003 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O CL UNIT 196 192 8 8 8 MERG 2 DFIX 1.73 0.02 C81 Cl1 C81 Cl2 C82 Cl3 C82 Cl4 C83 Cl5 C83 Cl6 C84 Cl7 C84 Cl8 DFIX 2.88 0.04 Cl1 Cl2 Cl3 Cl4 Cl5 Cl6 Cl7 Cl8 FMAP 2 PLAN 10 SIZE 0.200 0.250 0.600 ACTA BOND $H CONF L.S. 10 TEMP 22.00 WGHT 0.092900 0.482500 EXTI 0.002124 FVAR 7.29305 0.15797 C3 1 0.563694 -0.071498 0.276557 11.00000 0.07089 0.04514 = 0.04600 0.00042 0.00382 0.01351 AFIX 13 H3 2 0.646418 -0.060462 0.296253 11.00000 -1.20000 AFIX 0 C8 1 0.459065 -0.054473 0.326739 11.00000 0.06771 0.03833 = 0.04821 -0.00151 0.00563 0.00076 AFIX 13 H8 2 0.377104 -0.056070 0.303621 11.00000 -1.20000 AFIX 0 C7 1 0.453010 -0.105875 0.383612 11.00000 0.11481 0.05168 = 0.06321 0.01076 0.02322 0.00474 AFIX 23 H7A 2 0.527741 -0.100318 0.411225 11.00000 -1.20000 H7B 2 0.378494 -0.096388 0.410352 11.00000 -1.20000 AFIX 0 C6 1 0.446738 -0.178485 0.359965 11.00000 0.14908 0.04835 = 0.09599 0.01767 0.01966 -0.00222 AFIX 23 H6A 2 0.444822 -0.208898 0.397435 11.00000 -1.20000 H6B 2 0.369616 -0.185429 0.334486 11.00000 -1.20000 AFIX 0 C5 1 0.561316 -0.193247 0.318242 11.00000 0.17525 0.04895 = 0.08739 0.01151 0.02085 0.03550 AFIX 23 H5A 2 0.559156 -0.240074 0.304008 11.00000 -1.20000 H5B 2 0.638212 -0.186493 0.343951 11.00000 -1.20000 AFIX 0 C4 1 0.563400 -0.147413 0.258897 11.00000 0.14772 0.04491 = 0.06977 -0.00086 0.01433 0.02752 AFIX 23 H4A 2 0.489346 -0.157010 0.231854 11.00000 -1.20000 H4B 2 0.638698 -0.157439 0.232939 11.00000 -1.20000 AFIX 0 C1 1 0.637255 0.017267 0.201617 11.00000 0.05035 0.04439 = 0.04028 -0.00703 -0.00068 0.00424 C2 1 0.384222 0.061166 0.339360 11.00000 0.04682 0.03978 = 0.03983 -0.00018 0.00250 -0.00144 C9 1 0.449606 -0.053065 0.170270 11.00000 0.06967 0.05320 = 0.05144 -0.00062 -0.00515 -0.01319 AFIX 137 H9A 2 0.439588 -0.019988 0.136048 11.00000 -1.20000 H9B 2 0.370863 -0.057695 0.193942 11.00000 -1.20000 H9C 2 0.472421 -0.095790 0.151132 11.00000 -1.20000 AFIX 0 C9' 1 0.576850 0.023620 0.401759 11.00000 0.06577 0.05962 = 0.05722 -0.00956 -0.01319 0.01683 AFIX 137 H9'A 2 0.589700 0.070991 0.409794 11.00000 -1.20000 H9'B 2 0.653938 0.004195 0.384671 11.00000 -1.20000 H9'C 2 0.554442 0.001491 0.442214 11.00000 -1.20000 AFIX 0 C10 1 0.648764 0.044974 0.128859 11.00000 0.04984 0.04574 = 0.03971 -0.00691 0.00012 0.00017 C31 1 0.767882 0.091060 0.125484 11.00000 0.05090 0.04946 = 0.04725 -0.00252 -0.00145 -0.00161 C32 1 0.765443 0.153248 0.157945 11.00000 0.05705 0.05708 = 0.06757 -0.01490 0.00328 -0.00451 AFIX 43 H32 2 0.694748 0.164658 0.183256 11.00000 -1.20000 AFIX 0 C33 1 0.865685 0.198169 0.153286 11.00000 0.06927 0.05905 = 0.08821 -0.01649 -0.00383 -0.00966 AFIX 43 H33 2 0.862288 0.239279 0.175486 11.00000 -1.20000 AFIX 0 C34 1 0.971101 0.182093 0.115650 11.00000 0.05794 0.07094 = 0.09317 -0.00209 -0.00118 -0.01608 AFIX 43 H34 2 1.038233 0.212598 0.111987 11.00000 -1.20000 AFIX 0 C35 1 0.976558 0.120931 0.083637 11.00000 0.05842 0.07998 = 0.08670 -0.01006 0.01378 -0.00711 AFIX 43 H35 2 1.047904 0.109718 0.058732 11.00000 -1.20000 AFIX 0 C36 1 0.875200 0.075781 0.088520 11.00000 0.05838 0.06231 = 0.06610 -0.01307 0.01022 -0.00270 AFIX 43 H36 2 0.879543 0.034559 0.066561 11.00000 -1.20000 AFIX 0 C21 1 0.667798 -0.018200 0.084636 11.00000 0.04954 0.04904 = 0.04428 -0.00921 0.00470 -0.00373 C22 1 0.744925 -0.070312 0.107505 11.00000 0.06155 0.05264 = 0.05463 -0.00736 0.00388 0.00505 AFIX 43 H22 2 0.783040 -0.066299 0.148666 11.00000 -1.20000 AFIX 0 C23 1 0.766475 -0.128119 0.070513 11.00000 0.06686 0.05139 = 0.07877 -0.00994 0.01717 0.00348 AFIX 43 H23 2 0.816527 -0.162867 0.087394 11.00000 -1.20000 AFIX 0 C24 1 0.713353 -0.134012 0.008415 11.00000 0.07456 0.05908 = 0.07307 -0.02646 0.02536 -0.01399 AFIX 43 H24 2 0.729457 -0.172047 -0.017223 11.00000 -1.20000 AFIX 0 C25 1 0.637136 -0.083465 -0.014801 11.00000 0.07468 0.07712 = 0.05368 -0.02272 0.00962 -0.01833 AFIX 43 H25 2 0.600937 -0.087445 -0.056424 11.00000 -1.20000 AFIX 0 C26 1 0.612641 -0.026090 0.022702 11.00000 0.06070 0.06318 = 0.04576 -0.01018 0.00077 -0.00473 AFIX 43 H26 2 0.558937 0.007339 0.006298 11.00000 -1.20000 AFIX 0 C11 1 0.536146 0.090642 0.108107 11.00000 0.05267 0.04186 = 0.04572 -0.00454 -0.00365 -0.00316 C12 1 0.429998 0.102017 0.147192 11.00000 0.05378 0.04944 = 0.04869 -0.00794 -0.00372 0.00061 AFIX 43 H12 2 0.424837 0.081755 0.188434 11.00000 -1.20000 AFIX 0 C13 1 0.331132 0.143273 0.125646 11.00000 0.05624 0.05879 = 0.07079 -0.01527 -0.00627 0.00891 AFIX 43 H13 2 0.260132 0.149727 0.152349 11.00000 -1.20000 AFIX 0 C14 1 0.337057 0.174422 0.065747 11.00000 0.07181 0.05889 = 0.08035 -0.00197 -0.01779 0.01263 AFIX 43 H14 2 0.269741 0.201146 0.051193 11.00000 -1.20000 AFIX 0 C15 1 0.444116 0.165855 0.026926 11.00000 0.08281 0.06379 = 0.06600 0.01534 -0.01285 0.00141 AFIX 43 H15 2 0.449750 0.187905 -0.013421 11.00000 -1.20000 AFIX 0 C16 1 0.542912 0.124703 0.047696 11.00000 0.06517 0.05914 = 0.05650 0.00755 0.00057 -0.00362 AFIX 43 H16 2 0.614665 0.119581 0.021259 11.00000 -1.20000 AFIX 0 C20 1 0.370615 0.125977 0.384449 11.00000 0.04193 0.03996 = 0.03746 -0.00162 0.00140 -0.00017 C61 1 0.251204 0.165758 0.362420 11.00000 0.04491 0.04081 = 0.04304 -0.00019 -0.00044 -0.00079 C62 1 0.249921 0.195361 0.300144 11.00000 0.05515 0.05943 = 0.04652 0.00660 0.00344 0.00576 AFIX 43 H62 2 0.319648 0.189494 0.272437 11.00000 -1.20000 AFIX 0 C63 1 0.147485 0.233172 0.278708 11.00000 0.06898 0.06686 = 0.05758 0.01289 -0.00966 0.00763 AFIX 43 H63 2 0.148516 0.252223 0.236841 11.00000 -1.20000 AFIX 0 C64 1 0.043310 0.242806 0.319317 11.00000 0.05121 0.06343 = 0.08098 0.00763 -0.01062 0.00706 AFIX 43 H64 2 -0.026256 0.267935 0.304895 11.00000 -1.20000 AFIX 0 C65 1 0.043736 0.214795 0.381302 11.00000 0.04874 0.06616 = 0.07738 0.00790 0.00848 0.00788 AFIX 43 H65 2 -0.025578 0.221550 0.409093 11.00000 -1.20000 AFIX 0 C66 1 0.146715 0.176505 0.402806 11.00000 0.04961 0.05666 = 0.05325 0.00719 0.00732 0.00467 AFIX 43 H66 2 0.145483 0.157854 0.444842 11.00000 -1.20000 AFIX 0 C51 1 0.352742 0.097189 0.454578 11.00000 0.04475 0.04311 = 0.04003 0.00128 0.00408 0.00396 C52 1 0.266292 0.044119 0.462716 11.00000 0.05447 0.05290 = 0.04932 0.00386 0.00340 -0.00496 AFIX 43 H52 2 0.218027 0.029691 0.426961 11.00000 -1.20000 AFIX 0 C53 1 0.251190 0.012598 0.523121 11.00000 0.06099 0.05856 = 0.06411 0.01622 0.01359 -0.00505 AFIX 43 H53 2 0.193686 -0.022955 0.527314 11.00000 -1.20000 AFIX 0 C54 1 0.320450 0.033381 0.576984 11.00000 0.06440 0.07625 = 0.05035 0.02070 0.01094 0.00983 AFIX 43 H54 2 0.310980 0.011748 0.617353 11.00000 -1.20000 AFIX 0 C55 1 0.404104 0.086746 0.570247 11.00000 0.05903 0.07661 = 0.04006 0.00522 -0.00036 0.00596 AFIX 43 H55 2 0.450215 0.101709 0.606548 11.00000 -1.20000 AFIX 0 C56 1 0.420162 0.118443 0.509554 11.00000 0.05545 0.05482 = 0.04011 0.00237 0.00052 0.00090 AFIX 43 H56 2 0.476926 0.154385 0.505846 11.00000 -1.20000 AFIX 0 C41 1 0.482868 0.175705 0.377357 11.00000 0.04488 0.03973 = 0.03941 0.00121 -0.00100 0.00041 C46 1 0.481885 0.235313 0.414165 11.00000 0.05670 0.04029 = 0.04687 -0.00173 0.00187 0.00294 AFIX 43 H46 2 0.413638 0.244239 0.442080 11.00000 -1.20000 AFIX 0 C45 1 0.581207 0.281478 0.409745 11.00000 0.07166 0.03749 = 0.05540 -0.00076 -0.00962 -0.00448 AFIX 43 H45 2 0.579777 0.320527 0.435277 11.00000 -1.20000 AFIX 0 C44 1 0.681997 0.269732 0.367684 11.00000 0.06082 0.05477 = 0.06831 0.00366 -0.00544 -0.01701 AFIX 43 H44 2 0.749483 0.300159 0.365399 11.00000 -1.20000 AFIX 0 C43 1 0.681628 0.212529 0.329150 11.00000 0.05525 0.07153 = 0.06379 -0.00632 0.01185 -0.01402 AFIX 43 H43 2 0.748081 0.204971 0.299738 11.00000 -1.20000 AFIX 0 C42 1 0.582754 0.165868 0.333766 11.00000 0.05212 0.05038 = 0.05201 -0.01005 0.00691 -0.00681 AFIX 43 H42 2 0.583719 0.127535 0.307220 11.00000 -1.20000 AFIX 0 N1 3 0.549447 -0.031449 0.215219 11.00000 0.05685 0.04420 = 0.04061 -0.00242 -0.00087 0.00418 N2 3 0.474175 0.014775 0.354016 11.00000 0.05385 0.04186 = 0.04253 -0.00489 -0.00055 0.00312 O1 4 0.713087 0.036203 0.243320 11.00000 0.06467 0.07218 = 0.04524 -0.00638 -0.00916 -0.00674 O2 4 0.306578 0.051901 0.295246 11.00000 0.05927 0.05150 = 0.05108 -0.00973 -0.01103 0.00123 PART 1 C81 1 0.492055 0.014092 0.790720 10.68000 0.10091 0.18012 = 0.11869 0.05112 0.02224 -0.01564 AFIX 23 H81A 2 0.566880 -0.006488 0.771054 10.68000 -1.20000 H81B 2 0.425963 -0.020079 0.793885 10.68000 -1.20000 AFIX 0 CL1 5 0.440828 0.079141 0.743074 10.68000 0.28394 0.24318 = 0.09898 0.08062 -0.05359 -0.06901 CL2 5 0.528715 0.044107 0.867996 10.68000 0.23473 0.30763 = 0.08879 0.04198 -0.04580 -0.04595 PART 2 C82 1 0.508306 -0.048030 0.781453 10.14000 21.00000 AFIX 23 H82A 2 0.439951 -0.080651 0.786644 10.14000 -1.20000 H82B 2 0.585291 -0.071108 0.767454 10.14000 -1.20000 AFIX 0 CL3 5 0.464648 0.019715 0.725180 10.14000 21.00000 CL4 5 0.532655 -0.001494 0.852560 10.14000 21.00000 PART 3 C83 1 0.436282 0.092940 0.856440 10.13000 21.00000 AFIX 23 H83A 2 0.423669 0.045742 0.867775 10.13000 -1.20000 H83B 2 0.388812 0.120398 0.887521 10.13000 -1.20000 AFIX 0 CL5 5 0.599708 0.113227 0.860724 10.13000 21.00000 CL6 5 0.381931 0.107897 0.777275 10.13000 21.00000 PART 4 C84 1 0.445772 0.027589 0.790112 10.05000 21.00000 AFIX 23 H84A 2 0.354861 0.036534 0.789070 10.05000 -1.20000 H84B 2 0.469989 0.022828 0.835974 10.05000 -1.20000 AFIX 0 CL7 5 0.523328 0.097759 0.758764 10.05000 21.00000 CL8 5 0.472629 -0.050023 0.751045 10.05000 21.00000 HKLF 4 REM chnmeap in P2(1)2(1)2(1) REM R1 = 0.0449 for 8690 Fo > 4sig(Fo) and 0.0452 for all 8783 data REM 527 parameters refined using 12 restraints END WGHT 0.0929 0.4825 REM Highest difference peak 0.309, deepest hole -0.342, 1-sigma level 0.036 Q1 1 0.5609 -0.0733 0.8072 11.00000 0.05 0.28 Q2 1 0.5837 0.0793 0.8452 11.00000 0.05 0.25 Q3 1 0.4398 0.0819 0.8700 11.00000 0.05 0.24 Q4 1 0.6431 0.1253 0.8692 11.00000 0.05 0.20 Q5 1 0.3921 0.1017 0.8318 11.00000 0.05 0.16 Q6 1 0.5839 0.1332 0.8538 11.00000 0.05 0.15 Q7 1 0.3496 0.1228 0.7512 11.00000 0.05 0.15 Q8 1 0.3615 0.1185 0.4165 11.00000 0.05 0.15 Q9 1 0.4241 0.1449 0.3807 11.00000 0.05 0.14 Q10 1 0.3821 0.0975 0.3658 11.00000 0.05 0.14 ; _cod_data_source_file c5ra15554a2.cif _cod_data_source_block 4b _cod_database_code 7222304 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C3 C 0.5637(2) -0.07150(8) 0.27656(8) 0.0540(4) Uani 1 1 d . . . H3 H 0.6464 -0.0605 0.2963 0.065 Uiso 1 1 calc R . . C8 C 0.45907(19) -0.05447(8) 0.32674(8) 0.0514(4) Uani 1 1 d . . . H8 H 0.3771 -0.0561 0.3036 0.062 Uiso 1 1 calc R . . C7 C 0.4530(3) -0.10587(10) 0.38361(11) 0.0766(6) Uani 1 1 d . . . H7A H 0.5277 -0.1003 0.4112 0.092 Uiso 1 1 calc R . . H7B H 0.3785 -0.0964 0.4104 0.092 Uiso 1 1 calc R . . C6 C 0.4467(4) -0.17848(11) 0.35997(16) 0.0978(9) Uani 1 1 d . . . H6A H 0.4448 -0.2089 0.3974 0.117 Uiso 1 1 calc R . . H6B H 0.3696 -0.1854 0.3345 0.117 Uiso 1 1 calc R . . C5 C 0.5613(4) -0.19325(12) 0.31824(14) 0.1039(11) Uani 1 1 d . . . H5A H 0.5592 -0.2401 0.3040 0.125 Uiso 1 1 calc R . . H5B H 0.6382 -0.1865 0.3440 0.125 Uiso 1 1 calc R . . C4 C 0.5634(4) -0.14741(10) 0.25890(12) 0.0875(8) Uani 1 1 d . . . H4A H 0.4893 -0.1570 0.2319 0.105 Uiso 1 1 calc R . . H4B H 0.6387 -0.1574 0.2329 0.105 Uiso 1 1 calc R . . C1 C 0.63725(16) 0.01727(8) 0.20162(7) 0.0450(3) Uani 1 1 d . . . C2 C 0.38422(14) 0.06117(7) 0.33936(7) 0.0421(3) Uani 1 1 d . . . C9 C 0.4496(2) -0.05307(9) 0.17027(9) 0.0581(4) Uani 1 1 d . . . H9A H 0.4396 -0.0200 0.1360 0.070 Uiso 1 1 calc R . . H9B H 0.3709 -0.0577 0.1939 0.070 Uiso 1 1 calc R . . H9C H 0.4724 -0.0958 0.1511 0.070 Uiso 1 1 calc R . . C9' C 0.5768(2) 0.02362(10) 0.40176(10) 0.0609(4) Uani 1 1 d . . . H9'A H 0.5897 0.0710 0.4098 0.073 Uiso 1 1 calc R . . H9'B H 0.6539 0.0042 0.3847 0.073 Uiso 1 1 calc R . . H9'C H 0.5544 0.0015 0.4422 0.073 Uiso 1 1 calc R . . C10 C 0.64876(16) 0.04497(8) 0.12886(7) 0.0451(3) Uani 1 1 d . . . C31 C 0.76788(16) 0.09106(8) 0.12548(8) 0.0492(3) Uani 1 1 d . . . C32 C 0.76544(19) 0.15325(10) 0.15794(10) 0.0606(4) Uani 1 1 d . . . H32 H 0.6947 0.1647 0.1833 0.073 Uiso 1 1 calc R . . C33 C 0.8657(2) 0.19817(11) 0.15329(13) 0.0722(5) Uani 1 1 d . . . H33 H 0.8623 0.2393 0.1755 0.087 Uiso 1 1 calc R . . C34 C 0.9711(2) 0.18209(12) 0.11565(13) 0.0740(6) Uani 1 1 d . . . H34 H 1.0382 0.2126 0.1120 0.089 Uiso 1 1 calc R . . C35 C 0.9766(2) 0.12093(13) 0.08364(13) 0.0750(6) Uani 1 1 d . . . H35 H 1.0479 0.1097 0.0587 0.090 Uiso 1 1 calc R . . C36 C 0.87520(19) 0.07578(10) 0.08852(11) 0.0623(4) Uani 1 1 d . . . H36 H 0.8795 0.0346 0.0666 0.075 Uiso 1 1 calc R . . C21 C 0.66780(15) -0.01820(8) 0.08464(8) 0.0476(3) Uani 1 1 d . . . C22 C 0.74492(18) -0.07031(9) 0.10751(9) 0.0563(4) Uani 1 1 d . . . H22 H 0.7830 -0.0663 0.1487 0.068 Uiso 1 1 calc R . . C23 C 0.7665(2) -0.12812(10) 0.07051(11) 0.0657(5) Uani 1 1 d . . . H23 H 0.8165 -0.1629 0.0874 0.079 Uiso 1 1 calc R . . C24 C 0.7134(2) -0.13401(11) 0.00841(11) 0.0689(5) Uani 1 1 d . . . H24 H 0.7295 -0.1720 -0.0172 0.083 Uiso 1 1 calc R . . C25 C 0.6371(2) -0.08346(12) -0.01480(10) 0.0685(5) Uani 1 1 d . . . H25 H 0.6009 -0.0874 -0.0564 0.082 Uiso 1 1 calc R . . C26 C 0.61264(18) -0.02609(10) 0.02270(9) 0.0565(4) Uani 1 1 d . . . H26 H 0.5589 0.0073 0.0063 0.068 Uiso 1 1 calc R . . C11 C 0.53615(16) 0.09064(8) 0.10811(8) 0.0467(3) Uani 1 1 d . . . C12 C 0.43000(16) 0.10202(8) 0.14719(8) 0.0506(3) Uani 1 1 d . . . H12 H 0.4248 0.0818 0.1884 0.061 Uiso 1 1 calc R . . C13 C 0.33113(19) 0.14327(10) 0.12565(11) 0.0619(4) Uani 1 1 d . . . H13 H 0.2601 0.1497 0.1523 0.074 Uiso 1 1 calc R . . C14 C 0.3371(2) 0.17442(11) 0.06575(12) 0.0703(5) Uani 1 1 d . . . H14 H 0.2697 0.2011 0.0512 0.084 Uiso 1 1 calc R . . C15 C 0.4441(2) 0.16585(11) 0.02693(11) 0.0709(5) Uani 1 1 d . . . H15 H 0.4498 0.1879 -0.0134 0.085 Uiso 1 1 calc R . . C16 C 0.5429(2) 0.12470(10) 0.04770(10) 0.0603(4) Uani 1 1 d . . . H16 H 0.6147 0.1196 0.0213 0.072 Uiso 1 1 calc R . . C20 C 0.37061(13) 0.12598(7) 0.38445(7) 0.0398(3) Uani 1 1 d . . . C61 C 0.25120(14) 0.16576(7) 0.36242(7) 0.0429(3) Uani 1 1 d . . . C62 C 0.24992(18) 0.19536(9) 0.30014(9) 0.0537(4) Uani 1 1 d . . . H62 H 0.3196 0.1895 0.2724 0.064 Uiso 1 1 calc R . . C63 C 0.1475(2) 0.23317(11) 0.27871(10) 0.0645(5) Uani 1 1 d . . . H63 H 0.1485 0.2522 0.2368 0.077 Uiso 1 1 calc R . . C64 C 0.04331(18) 0.24281(11) 0.31932(11) 0.0652(5) Uani 1 1 d . . . H64 H -0.0263 0.2679 0.3049 0.078 Uiso 1 1 calc R . . C65 C 0.04374(19) 0.21480(11) 0.38130(11) 0.0641(5) Uani 1 1 d . . . H65 H -0.0256 0.2215 0.4091 0.077 Uiso 1 1 calc R . . C66 C 0.14671(17) 0.17650(9) 0.40281(9) 0.0532(4) Uani 1 1 d . . . H66 H 0.1455 0.1579 0.4448 0.064 Uiso 1 1 calc R . . C51 C 0.35274(15) 0.09719(7) 0.45458(7) 0.0426(3) Uani 1 1 d . . . C52 C 0.26629(17) 0.04412(9) 0.46272(9) 0.0522(4) Uani 1 1 d . . . H52 H 0.2180 0.0297 0.4270 0.063 Uiso 1 1 calc R . . C53 C 0.25119(19) 0.01260(10) 0.52312(10) 0.0612(4) Uani 1 1 d . . . H53 H 0.1937 -0.0230 0.5273 0.073 Uiso 1 1 calc R . . C54 C 0.3205(2) 0.03338(11) 0.57698(9) 0.0637(5) Uani 1 1 d . . . H54 H 0.3110 0.0117 0.6174 0.076 Uiso 1 1 calc R . . C55 C 0.40410(18) 0.08675(11) 0.57025(8) 0.0586(4) Uani 1 1 d . . . H55 H 0.4502 0.1017 0.6065 0.070 Uiso 1 1 calc R . . C56 C 0.42016(17) 0.11844(9) 0.50955(8) 0.0501(3) Uani 1 1 d . . . H56 H 0.4769 0.1544 0.5058 0.060 Uiso 1 1 calc R . . C41 C 0.48287(14) 0.17570(7) 0.37736(7) 0.0413(3) Uani 1 1 d . . . C46 C 0.48188(17) 0.23531(8) 0.41416(8) 0.0480(3) Uani 1 1 d . . . H46 H 0.4136 0.2442 0.4421 0.058 Uiso 1 1 calc R . . C45 C 0.58121(19) 0.28148(8) 0.40974(9) 0.0549(4) Uani 1 1 d . . . H45 H 0.5798 0.3205 0.4353 0.066 Uiso 1 1 calc R . . C44 C 0.68200(19) 0.26973(10) 0.36768(10) 0.0613(4) Uani 1 1 d . . . H44 H 0.7495 0.3002 0.3654 0.074 Uiso 1 1 calc R . . C43 C 0.68163(19) 0.21253(11) 0.32915(11) 0.0635(5) Uani 1 1 d . . . H43 H 0.7481 0.2050 0.2997 0.076 Uiso 1 1 calc R . . C42 C 0.58275(17) 0.16587(9) 0.33377(9) 0.0515(4) Uani 1 1 d . . . H42 H 0.5837 0.1275 0.3072 0.062 Uiso 1 1 calc R . . N1 N 0.54945(14) -0.03145(7) 0.21522(6) 0.0472(3) Uani 1 1 d . . . N2 N 0.47417(13) 0.01478(7) 0.35402(6) 0.0461(3) Uani 1 1 d . . . O1 O 0.71309(13) 0.03620(7) 0.24332(6) 0.0607(3) Uani 1 1 d . . . O2 O 0.30658(12) 0.05190(6) 0.29525(6) 0.0539(3) Uani 1 1 d . . . C81 C 0.4921(6) 0.0141(4) 0.7907(3) 0.133(3) Uani 0.68 1 d PD A 1 H81A H 0.5669 -0.0065 0.7711 0.160 Uiso 0.68 1 calc PR A 1 H81B H 0.4260 -0.0201 0.7939 0.160 Uiso 0.68 1 calc PR A 1 Cl1 Cl 0.4408(4) 0.07914(18) 0.74307(10) 0.2087(15) Uani 0.68 1 d PD A 1 Cl2 Cl 0.5287(3) 0.0441(2) 0.86800(9) 0.2104(14) Uani 0.68 1 d PD A 1 C82 C 0.508(5) -0.0480(13) 0.7815(11) 0.1580(17) Uiso 0.14 1 d PD B 2 H82A H 0.4400 -0.0807 0.7866 0.190 Uiso 0.14 1 calc PR B 2 H82B H 0.5853 -0.0711 0.7675 0.190 Uiso 0.14 1 calc PR B 2 Cl3 Cl 0.4646(12) 0.0197(7) 0.7252(6) 0.1580(17) Uiso 0.14 1 d PD B 2 Cl4 Cl 0.5327(14) -0.0015(7) 0.8526(7) 0.1580(17) Uiso 0.14 1 d PD B 2 C83 C 0.436(2) 0.093(2) 0.8564(13) 0.1580(17) Uiso 0.13 1 d PD C 3 H83A H 0.4237 0.0457 0.8678 0.190 Uiso 0.13 1 calc PR C 3 H83B H 0.3888 0.1204 0.8875 0.190 Uiso 0.13 1 calc PR C 3 Cl5 Cl 0.5997(11) 0.1132(6) 0.8607(6) 0.1580(17) Uiso 0.13 1 d PD C 3 Cl6 Cl 0.3819(12) 0.1079(7) 0.7773(7) 0.1580(17) Uiso 0.13 1 d PD C 3 C84 C 0.446(13) 0.028(2) 0.790(6) 0.1580(17) Uiso 0.05 1 d PD D 4 H84A H 0.3549 0.0365 0.7891 0.190 Uiso 0.05 1 calc PR D 4 H84B H 0.4700 0.0228 0.8360 0.190 Uiso 0.05 1 calc PR D 4 Cl7 Cl 0.523(3) 0.0978(15) 0.7588(19) 0.1580(17) Uiso 0.05 1 d PD D 4 Cl8 Cl 0.473(3) -0.0500(14) 0.7510(18) 0.1580(17) Uiso 0.05 1 d PD D 4 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 C3 0.0709(10) 0.0451(8) 0.0460(8) 0.0004(6) 0.0038(7) 0.0135(8) C8 0.0677(10) 0.0383(7) 0.0482(8) -0.0015(6) 0.0056(7) 0.0008(7) C7 0.1148(18) 0.0517(9) 0.0632(11) 0.0108(8) 0.0232(12) 0.0047(11) C6 0.149(3) 0.0484(10) 0.0960(17) 0.0177(11) 0.0197(19) -0.0022(14) C5 0.175(3) 0.0490(10) 0.0874(16) 0.0115(11) 0.021(2) 0.0355(16) C4 0.148(2) 0.0449(9) 0.0698(12) -0.0009(8) 0.0143(15) 0.0275(13) C1 0.0504(8) 0.0444(7) 0.0403(7) -0.0070(6) -0.0007(6) 0.0042(6) C2 0.0468(7) 0.0398(7) 0.0398(7) -0.0002(5) 0.0025(6) -0.0014(5) C9 0.0697(10) 0.0532(8) 0.0514(9) -0.0006(7) -0.0052(8) -0.0132(8) C9' 0.0658(10) 0.0596(9) 0.0572(9) -0.0096(8) -0.0132(8) 0.0168(8) C10 0.0498(7) 0.0457(7) 0.0397(7) -0.0069(6) 0.0001(6) 0.0002(6) C31 0.0509(8) 0.0495(8) 0.0473(8) -0.0025(6) -0.0015(7) -0.0016(6) C32 0.0570(9) 0.0571(9) 0.0676(10) -0.0149(8) 0.0033(8) -0.0045(8) C33 0.0693(12) 0.0591(10) 0.0882(14) -0.0165(10) -0.0038(11) -0.0097(9) C34 0.0579(10) 0.0709(12) 0.0932(15) -0.0021(11) -0.0012(11) -0.0161(9) C35 0.0584(10) 0.0800(14) 0.0867(14) -0.0101(12) 0.0138(10) -0.0071(10) C36 0.0584(9) 0.0623(10) 0.0661(11) -0.0131(9) 0.0102(8) -0.0027(8) C21 0.0495(8) 0.0490(8) 0.0443(7) -0.0092(6) 0.0047(6) -0.0037(6) C22 0.0616(9) 0.0526(9) 0.0546(9) -0.0074(7) 0.0039(8) 0.0051(8) C23 0.0669(11) 0.0514(9) 0.0788(12) -0.0099(9) 0.0172(10) 0.0035(8) C24 0.0746(12) 0.0591(10) 0.0731(12) -0.0265(9) 0.0254(10) -0.0140(9) C25 0.0747(12) 0.0771(12) 0.0537(10) -0.0227(9) 0.0096(9) -0.0183(10) C26 0.0607(9) 0.0632(10) 0.0458(8) -0.0102(7) 0.0008(7) -0.0047(8) C11 0.0527(8) 0.0419(7) 0.0457(7) -0.0045(6) -0.0037(6) -0.0032(6) C12 0.0538(8) 0.0494(8) 0.0487(8) -0.0079(6) -0.0037(7) 0.0006(7) C13 0.0562(9) 0.0588(9) 0.0708(11) -0.0153(9) -0.0063(8) 0.0089(8) C14 0.0718(12) 0.0589(10) 0.0803(13) -0.0020(9) -0.0178(10) 0.0126(9) C15 0.0828(13) 0.0638(11) 0.0660(11) 0.0153(9) -0.0128(10) 0.0014(10) C16 0.0652(10) 0.0591(9) 0.0565(9) 0.0076(8) 0.0006(8) -0.0036(8) C20 0.0419(7) 0.0400(6) 0.0375(6) -0.0016(5) 0.0014(5) -0.0002(5) C61 0.0449(7) 0.0408(7) 0.0430(7) -0.0002(5) -0.0004(6) -0.0008(6) C62 0.0551(9) 0.0594(9) 0.0465(8) 0.0066(7) 0.0034(7) 0.0058(7) C63 0.0690(11) 0.0669(10) 0.0576(10) 0.0129(8) -0.0097(9) 0.0076(9) C64 0.0512(9) 0.0634(10) 0.0810(13) 0.0076(9) -0.0106(9) 0.0071(8) C65 0.0487(9) 0.0662(10) 0.0774(12) 0.0079(9) 0.0085(9) 0.0079(8) C66 0.0496(8) 0.0567(9) 0.0532(9) 0.0072(7) 0.0073(7) 0.0047(7) C51 0.0447(7) 0.0431(7) 0.0400(7) 0.0013(5) 0.0041(6) 0.0040(6) C52 0.0545(8) 0.0529(8) 0.0493(8) 0.0039(7) 0.0034(7) -0.0050(7) C53 0.0610(9) 0.0586(10) 0.0641(10) 0.0162(8) 0.0136(8) -0.0051(8) C54 0.0644(10) 0.0763(12) 0.0504(9) 0.0207(8) 0.0109(8) 0.0098(9) C55 0.0590(9) 0.0766(11) 0.0401(8) 0.0052(8) -0.0004(7) 0.0060(9) C56 0.0555(8) 0.0548(8) 0.0401(7) 0.0024(6) 0.0005(6) 0.0009(7) C41 0.0449(7) 0.0397(6) 0.0394(6) 0.0012(5) -0.0010(6) 0.0004(5) C46 0.0567(8) 0.0403(7) 0.0469(7) -0.0017(6) 0.0019(7) 0.0029(6) C45 0.0717(10) 0.0375(7) 0.0554(9) -0.0008(6) -0.0096(8) -0.0045(7) C44 0.0608(10) 0.0548(9) 0.0683(11) 0.0037(8) -0.0054(8) -0.0170(8) C43 0.0553(9) 0.0715(11) 0.0638(10) -0.0063(9) 0.0119(8) -0.0140(9) C42 0.0521(8) 0.0504(8) 0.0520(8) -0.0100(7) 0.0069(7) -0.0068(7) N1 0.0569(7) 0.0442(6) 0.0406(6) -0.0024(5) -0.0009(5) 0.0042(6) N2 0.0538(7) 0.0419(6) 0.0425(6) -0.0049(5) -0.0005(5) 0.0031(5) O1 0.0647(7) 0.0722(8) 0.0452(6) -0.0064(5) -0.0092(5) -0.0067(6) O2 0.0593(6) 0.0515(6) 0.0511(6) -0.0097(5) -0.0110(5) 0.0012(5) C81 0.101(4) 0.180(7) 0.119(4) 0.051(4) 0.022(3) -0.016(4) Cl1 0.284(3) 0.243(3) 0.0990(11) 0.0806(17) -0.0536(17) -0.069(3) Cl2 0.235(3) 0.308(4) 0.0888(10) 0.0420(16) -0.0458(14) -0.046(3) 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 N1 C3 C8 111.62(13) N1 C3 C4 108.88(15) C8 C3 C4 111.48(18) N1 C3 H3 108.2 C8 C3 H3 108.2 C4 C3 H3 108.2 N2 C8 C3 111.93(14) N2 C8 C7 109.44(14) C3 C8 C7 112.51(15) N2 C8 H8 107.6 C3 C8 H8 107.6 C7 C8 H8 107.6 C6 C7 C8 112.90(19) C6 C7 H7A 109.0 C8 C7 H7A 109.0 C6 C7 H7B 109.0 C8 C7 H7B 109.0 H7A C7 H7B 107.8 C5 C6 C7 109.2(3) C5 C6 H6A 109.8 C7 C6 H6A 109.8 C5 C6 H6B 109.8 C7 C6 H6B 109.8 H6A C6 H6B 108.3 C6 C5 C4 110.3(2) C6 C5 H5A 109.6 C4 C5 H5A 109.6 C6 C5 H5B 109.6 C4 C5 H5B 109.6 H5A C5 H5B 108.1 C5 C4 C3 113.5(2) C5 C4 H4A 108.9 C3 C4 H4A 108.9 C5 C4 H4B 108.9 C3 C4 H4B 108.9 H4A C4 H4B 107.7 O1 C1 N1 121.14(15) O1 C1 C10 119.52(15) N1 C1 C10 119.12(13) O2 C2 N2 121.66(13) O2 C2 C20 119.00(13) N2 C2 C20 119.09(12) N1 C9 H9A 109.5 N1 C9 H9B 109.5 H9A C9 H9B 109.5 N1 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 N2 C9' H9'A 109.5 N2 C9' H9'B 109.5 H9'A C9' H9'B 109.5 N2 C9' H9'C 109.5 H9'A C9' H9'C 109.5 H9'B C9' H9'C 109.5 C11 C10 C31 105.14(12) C11 C10 C21 114.25(12) C31 C10 C21 110.14(13) C11 C10 C1 113.52(13) C31 C10 C1 107.88(12) C21 C10 C1 105.79(12) C36 C31 C32 117.56(16) C36 C31 C10 123.45(15) C32 C31 C10 118.87(15) C33 C32 C31 121.39(18) C33 C32 H32 119.3 C31 C32 H32 119.3 C32 C33 C34 120.00(19) C32 C33 H33 120.0 C34 C33 H33 120.0 C35 C34 C33 119.8(2) C35 C34 H34 120.1 C33 C34 H34 120.1 C34 C35 C36 119.9(2) C34 C35 H35 120.0 C36 C35 H35 120.0 C31 C36 C35 121.28(18) C31 C36 H36 119.4 C35 C36 H36 119.4 C22 C21 C26 117.42(16) C22 C21 C10 118.57(15) C26 C21 C10 124.02(16) C23 C22 C21 121.66(18) C23 C22 H22 119.2 C21 C22 H22 119.2 C24 C23 C22 119.9(2) C24 C23 H23 120.1 C22 C23 H23 120.1 C25 C24 C23 119.31(18) C25 C24 H24 120.3 C23 C24 H24 120.3 C24 C25 C26 121.11(19) C24 C25 H25 119.4 C26 C25 H25 119.4 C25 C26 C21 120.6(2) C25 C26 H26 119.7 C21 C26 H26 119.7 C12 C11 C16 117.66(16) C12 C11 C10 123.55(14) C16 C11 C10 118.74(15) C11 C12 C13 120.95(17) C11 C12 H12 119.5 C13 C12 H12 119.5 C14 C13 C12 120.8(2) C14 C13 H13 119.6 C12 C13 H13 119.6 C13 C14 C15 119.34(19) C13 C14 H14 120.3 C15 C14 H14 120.3 C14 C15 C16 120.44(19) C14 C15 H15 119.8 C16 C15 H15 119.8 C15 C16 C11 120.77(19) C15 C16 H16 119.6 C11 C16 H16 119.6 C41 C20 C61 105.53(11) C41 C20 C51 114.45(11) C61 C20 C51 110.86(12) C41 C20 C2 113.20(11) C61 C20 C2 108.53(12) C51 C20 C2 104.26(11) C66 C61 C62 117.73(15) C66 C61 C20 123.22(14) C62 C61 C20 118.97(14) C63 C62 C61 121.43(17) C63 C62 H62 119.3 C61 C62 H62 119.3 C62 C63 C64 120.14(18) C62 C63 H63 119.9 C64 C63 H63 119.9 C65 C64 C63 119.22(17) C65 C64 H64 120.4 C63 C64 H64 120.4 C64 C65 C66 120.64(18) C64 C65 H65 119.7 C66 C65 H65 119.7 C61 C66 C65 120.83(16) C61 C66 H66 119.6 C65 C66 H66 119.6 C56 C51 C52 117.61(14) C56 C51 C20 124.66(13) C52 C51 C20 117.68(13) C53 C52 C51 121.14(17) C53 C52 H52 119.4 C51 C52 H52 119.4 C54 C53 C52 120.63(17) C54 C53 H53 119.7 C52 C53 H53 119.7 C53 C54 C55 119.04(16) C53 C54 H54 120.5 C55 C54 H54 120.5 C54 C55 C56 120.59(18) C54 C55 H55 119.7 C56 C55 H55 119.7 C51 C56 C55 120.97(16) C51 C56 H56 119.5 C55 C56 H56 119.5 C42 C41 C46 117.80(14) C42 C41 C20 123.24(13) C46 C41 C20 118.88(13) C45 C46 C41 121.00(15) C45 C46 H46 119.5 C41 C46 H46 119.5 C44 C45 C46 120.32(15) C44 C45 H45 119.8 C46 C45 H45 119.8 C43 C44 C45 119.27(16) C43 C44 H44 120.4 C45 C44 H44 120.4 C44 C43 C42 120.59(18) C44 C43 H43 119.7 C42 C43 H43 119.7 C41 C42 C43 120.92(16) C41 C42 H42 119.5 C43 C42 H42 119.5 C1 N1 C9 124.62(14) C1 N1 C3 118.68(14) C9 N1 C3 116.30(14) C2 N2 C9' 125.53(13) C2 N2 C8 118.01(13) C9' N2 C8 115.91(14) Cl1 C81 Cl2 109.2(5) Cl1 C81 H81A 109.8 Cl2 C81 H81A 109.8 Cl1 C81 H81B 109.8 Cl2 C81 H81B 109.8 H81A C81 H81B 108.3 Cl4 C82 Cl3 99.8(13) Cl4 C82 H82A 111.8 Cl3 C82 H82A 111.8 Cl4 C82 H82B 111.8 Cl3 C82 H82B 111.8 H82A C82 H82B 109.5 Cl6 C83 Cl5 109.1(15) Cl6 C83 H83A 109.9 Cl5 C83 H83A 109.9 Cl6 C83 H83B 109.9 Cl5 C83 H83B 109.9 H83A C83 H83B 108.3 Cl7 C84 Cl8 117(3) Cl7 C84 H84A 107.9 Cl8 C84 H84A 107.9 Cl7 C84 H84B 107.9 Cl8 C84 H84B 107.9 H84A C84 H84B 107.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C3 N1 1.484(2) C3 C8 1.535(2) C3 C4 1.543(3) C3 H3 0.9800 C8 N2 1.485(2) C8 C7 1.540(2) C8 H8 0.9800 C7 C6 1.515(3) C7 H7A 0.9700 C7 H7B 0.9700 C6 C5 1.499(5) C6 H6A 0.9700 C6 H6B 0.9700 C5 C4 1.508(3) C5 H5A 0.9700 C5 H5B 0.9700 C4 H4A 0.9700 C4 H4B 0.9700 C1 O1 1.221(2) C1 N1 1.361(2) C1 C10 1.580(2) C2 O2 1.2245(19) C2 N2 1.349(2) C2 C20 1.5812(19) C9 N1 1.453(2) C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 C9' N2 1.460(2) C9' H9'A 0.9600 C9' H9'B 0.9600 C9' H9'C 0.9600 C10 C11 1.545(2) C10 C31 1.548(2) C10 C21 1.551(2) C31 C36 1.386(3) C31 C32 1.395(2) C32 C33 1.379(3) C32 H32 0.9300 C33 C34 1.381(3) C33 H33 0.9300 C34 C35 1.374(3) C34 H34 0.9300 C35 C36 1.392(3) C35 H35 0.9300 C36 H36 0.9300 C21 C22 1.390(3) C21 C26 1.393(2) C22 C23 1.386(3) C22 H22 0.9300 C23 C24 1.384(3) C23 H23 0.9300 C24 C25 1.364(4) C24 H24 0.9300 C25 C26 1.390(3) C25 H25 0.9300 C26 H26 0.9300 C11 C12 1.386(2) C11 C16 1.401(2) C12 C13 1.390(3) C12 H12 0.9300 C13 C14 1.365(3) C13 H13 0.9300 C14 C15 1.382(4) C14 H14 0.9300 C15 C16 1.383(3) C15 H15 0.9300 C16 H16 0.9300 C20 C41 1.540(2) C20 C61 1.545(2) C20 C51 1.5451(19) C61 C66 1.385(2) C61 C62 1.394(2) C62 C63 1.379(3) C62 H62 0.9300 C63 C64 1.382(3) C63 H63 0.9300 C64 C65 1.375(3) C64 H64 0.9300 C65 C66 1.389(3) C65 H65 0.9300 C66 H66 0.9300 C51 C56 1.387(2) C51 C52 1.396(2) C52 C53 1.385(2) C52 H52 0.9300 C53 C54 1.376(3) C53 H53 0.9300 C54 C55 1.379(3) C54 H54 0.9300 C55 C56 1.393(2) C55 H55 0.9300 C56 H56 0.9300 C41 C42 1.385(2) C41 C46 1.395(2) C46 C45 1.388(2) C46 H46 0.9300 C45 C44 1.379(3) C45 H45 0.9300 C44 C43 1.375(3) C44 H44 0.9300 C43 C42 1.391(2) C43 H43 0.9300 C42 H42 0.9300 C81 Cl1 1.697(7) C81 Cl2 1.721(8) C81 H81A 0.9700 C81 H81B 0.9700 C82 Cl4 1.731(19) C82 Cl3 1.819(19) C82 H82A 0.9700 C82 H82B 0.9700 C83 Cl6 1.731(19) C83 Cl5 1.763(19) C83 H83A 0.9700 C83 H83B 0.9700 C84 Cl7 1.73(2) C84 Cl8 1.75(2) C84 H84A 0.9700 C84 H84B 0.9700 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 N1 C3 C8 N2 -69.25(19) C4 C3 C8 N2 168.74(18) N1 C3 C8 C7 167.02(17) C4 C3 C8 C7 45.0(2) N2 C8 C7 C6 -176.0(2) C3 C8 C7 C6 -50.9(3) C8 C7 C6 C5 58.3(3) C7 C6 C5 C4 -60.9(4) C6 C5 C4 C3 57.9(4) N1 C3 C4 C5 -173.0(3) C8 C3 C4 C5 -49.4(3) O1 C1 C10 C11 -112.98(17) N1 C1 C10 C11 72.36(17) O1 C1 C10 C31 3.1(2) N1 C1 C10 C31 -171.56(13) O1 C1 C10 C21 120.95(15) N1 C1 C10 C21 -53.71(18) C11 C10 C31 C36 -124.51(18) C21 C10 C31 C36 -1.0(2) C1 C10 C31 C36 114.05(19) C11 C10 C31 C32 51.5(2) C21 C10 C31 C32 175.06(16) C1 C10 C31 C32 -69.92(19) C36 C31 C32 C33 0.3(3) C10 C31 C32 C33 -175.95(19) C31 C32 C33 C34 0.3(4) C32 C33 C34 C35 -0.9(4) C33 C34 C35 C36 0.8(4) C32 C31 C36 C35 -0.3(3) C10 C31 C36 C35 175.7(2) C34 C35 C36 C31 -0.2(4) C11 C10 C21 C22 -164.80(15) C31 C10 C21 C22 77.15(19) C1 C10 C21 C22 -39.19(19) C11 C10 C21 C26 15.6(2) C31 C10 C21 C26 -102.50(18) C1 C10 C21 C26 141.16(16) C26 C21 C22 C23 -0.1(3) C10 C21 C22 C23 -179.78(17) C21 C22 C23 C24 1.8(3) C22 C23 C24 C25 -1.9(3) C23 C24 C25 C26 0.4(3) C24 C25 C26 C21 1.4(3) C22 C21 C26 C25 -1.5(3) C10 C21 C26 C25 178.20(17) C31 C10 C11 C12 -122.66(16) C21 C10 C11 C12 116.47(16) C1 C10 C11 C12 -5.0(2) C31 C10 C11 C16 54.79(18) C21 C10 C11 C16 -66.08(19) C1 C10 C11 C16 172.48(14) C16 C11 C12 C13 3.0(2) C10 C11 C12 C13 -179.53(15) C11 C12 C13 C14 -1.0(3) C12 C13 C14 C15 -1.5(3) C13 C14 C15 C16 1.7(3) C14 C15 C16 C11 0.4(3) C12 C11 C16 C15 -2.7(3) C10 C11 C16 C15 179.67(17) O2 C2 C20 C41 -115.36(15) N2 C2 C20 C41 70.24(17) O2 C2 C20 C61 1.43(18) N2 C2 C20 C61 -172.97(13) O2 C2 C20 C51 119.64(15) N2 C2 C20 C51 -54.76(16) C41 C20 C61 C66 -121.03(16) C51 C20 C61 C66 3.4(2) C2 C20 C61 C66 117.35(16) C41 C20 C61 C62 55.70(18) C51 C20 C61 C62 -179.86(14) C2 C20 C61 C62 -65.92(17) C66 C61 C62 C63 -1.1(3) C20 C61 C62 C63 -177.99(17) C61 C62 C63 C64 0.4(3) C62 C63 C64 C65 0.6(3) C63 C64 C65 C66 -0.8(3) C62 C61 C66 C65 0.8(3) C20 C61 C66 C65 177.61(17) C64 C65 C66 C61 0.1(3) C41 C20 C51 C56 7.1(2) C61 C20 C51 C56 -112.15(17) C2 C20 C51 C56 131.25(15) C41 C20 C51 C52 -170.21(13) C61 C20 C51 C52 70.58(17) C2 C20 C51 C52 -46.02(17) C56 C51 C52 C53 -1.8(2) C20 C51 C52 C53 175.65(16) C51 C52 C53 C54 0.7(3) C52 C53 C54 C55 0.9(3) C53 C54 C55 C56 -1.2(3) C52 C51 C56 C55 1.5(2) C20 C51 C56 C55 -175.77(15) C54 C55 C56 C51 0.0(3) C61 C20 C41 C42 -115.95(16) C51 C20 C41 C42 121.89(16) C2 C20 C41 C42 2.6(2) C61 C20 C41 C46 60.93(17) C51 C20 C41 C46 -61.23(18) C2 C20 C41 C46 179.48(13) C42 C41 C46 C45 -3.3(2) C20 C41 C46 C45 179.62(14) C41 C46 C45 C44 1.2(3) C46 C45 C44 C43 1.4(3) C45 C44 C43 C42 -1.9(3) C46 C41 C42 C43 2.9(3) C20 C41 C42 C43 179.76(17) C44 C43 C42 C41 -0.3(3) O1 C1 N1 C9 174.92(16) C10 C1 N1 C9 -10.5(2) O1 C1 N1 C3 -12.6(2) C10 C1 N1 C3 161.96(13) C8 C3 N1 C1 110.58(17) C4 C3 N1 C1 -125.9(2) C8 C3 N1 C9 -76.33(18) C4 C3 N1 C9 47.2(2) O2 C2 N2 C9' 174.60(17) C20 C2 N2 C9' -11.2(2) O2 C2 N2 C8 -14.3(2) C20 C2 N2 C8 159.97(13) C3 C8 N2 C2 113.55(17) C7 C8 N2 C2 -121.02(18) C3 C8 N2 C9' -74.48(19) C7 C8 N2 C9' 51.0(2)