#------------------------------------------------------------------------------ #$Date: 2021-09-15 03:32:50 +0300 (Wed, 15 Sep 2021) $ #$Revision: 269146 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158299.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_7158299 loop_ _publ_author_name 'Wang, Yu' 'Niu, Cheng' 'Xie, Donghua' 'Du, Da-Ming' _publ_section_title ; Bifunctional squaramide‐catalysed enantioselective vinylogous Michael addition/cyclization cascade reaction of 4‐unsturated isoxazol‐5‐ones and \a,\a‐dicyanoalkenes ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01256H _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_sum 'C22 H16 Br N3 O2' _chemical_formula_weight 434.29 _chemical_melting_point 452.0(10) _chemical_name_systematic '(5S,10R)-8-(4-Bromophenyl)-6-imino-4-methyl-1-oxo-10-phenyl-2-oxa-3-azaspiro[4.5]de ca-3,7-diene-7-carbonitrile' _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_Hall 'P 1' _space_group_name_H-M_alt 'P 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-06-27 deposited with the CCDC. 2021-09-13 downloaded from the CCDC. ; _cell_angle_alpha 75.605(8) _cell_angle_beta 86.331(8) _cell_angle_gamma 89.054(9) _cell_formula_units_Z 2 _cell_length_a 6.062(2) _cell_length_b 12.279(5) _cell_length_c 13.666(5) _cell_measurement_reflns_used 5332 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 20.34 _cell_measurement_theta_min 2.57 _cell_volume 983.3(6) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type CCD _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0788 _diffrn_reflns_av_unetI/netI 0.1337 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 20517 _diffrn_reflns_point_group_measured_fraction_full 0.942 _diffrn_reflns_point_group_measured_fraction_max 0.937 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.279 _diffrn_reflns_theta_min 3.084 _exptl_absorpt_coefficient_mu 2.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.467 _exptl_crystal_description block _exptl_crystal_F_000 440 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Petroleum ether/ethyl acetate 5:1' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_transmission_factor_max 0.864 _exptl_transmission_factor_min 0.864 _refine_diff_density_max 0.263 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.057 _refine_ls_abs_structure_details ; Flack x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.023(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 507 _refine_ls_number_reflns 6734 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 0.901 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0433 _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^)+(0.0232P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.0977 _reflns_Friedel_coverage 0.897 _reflns_Friedel_fraction_full 0.891 _reflns_Friedel_fraction_max 0.886 _reflns_number_gt 3537 _reflns_number_total 6734 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01256h2.cif _cod_data_source_block 1_b _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value '451-453' was changed to '452.0(10)' -- the average value was taken and precision was estimated. data item '_chemical_absolute_configuration' value 'AD' was changed to 'ad' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 7158299 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.677 _shelx_estimated_absorpt_t_max 0.677 _shelx_res_file ; 1_b.res created by SHELXL-2014/7 TITL 1_b.res in P1 CELL 0.71073 6.0620 12.2792 13.6657 75.605 86.331 89.054 ZERR 2.000 0.0023 0.0047 0.0050 0.008 0.008 0.009 LATT -1 SFAC C H N O Br UNIT 44 32 6 4 2 omit 0 -1 -1 omit 0 1 1 omit 0 -1 0 omit 0 1 0 omit 0 0 -1 omit 0 0 1 L.S. 24 ACTA BOND $H FMAP 2 PLAN 20 LIST 6 conf size 0.2 0.2 0.2 TEMP 23.000 WGHT 0.023200 FVAR 0.80423 BR1 5 -0.080181 0.032886 0.893263 11.00000 0.11955 0.09534 = 0.04530 -0.00622 0.01126 -0.02607 BR2 5 1.084489 0.747828 0.099441 11.00000 0.08592 0.08313 = 0.04177 -0.01461 0.00754 0.00207 C1 1 -0.034599 0.228476 0.600623 11.00000 0.04448 0.06349 = 0.05016 -0.01616 0.00277 0.00267 AFIX 43 H1 2 -0.121502 0.282191 0.559979 11.00000 -1.20000 AFIX 0 C2 1 -0.108653 0.177737 0.698863 11.00000 0.04997 0.08536 = 0.04392 -0.02516 0.01233 -0.01354 AFIX 43 H2 2 -0.246034 0.197559 0.723561 11.00000 -1.20000 AFIX 0 C3 1 0.015327 0.099423 0.760122 11.00000 0.06166 0.06479 = 0.03942 -0.01580 0.00164 -0.01176 C4 1 0.219819 0.067801 0.721930 11.00000 0.07707 0.06195 = 0.04928 0.00081 -0.01567 -0.00541 AFIX 43 H4 2 0.305555 0.013670 0.762789 11.00000 -1.20000 AFIX 0 C5 1 0.294075 0.117471 0.622969 11.00000 0.06817 0.06129 = 0.04925 -0.00681 0.00816 0.01275 AFIX 43 H5 2 0.428586 0.095451 0.597241 11.00000 -1.20000 AFIX 0 C6 1 0.169913 0.199194 0.562548 11.00000 0.04347 0.04905 = 0.04524 -0.01233 0.00372 -0.00343 C7 1 0.250176 0.250154 0.457561 11.00000 0.03485 0.05440 = 0.03395 -0.00584 -0.00258 -0.00270 C8 1 0.261617 0.361892 0.417893 11.00000 0.03000 0.05266 = 0.04483 -0.01953 0.00230 0.00427 C9 1 0.344050 0.416694 0.316600 11.00000 0.02941 0.05266 = 0.04594 -0.01202 0.00323 0.00080 C10 1 0.458486 0.341029 0.256108 11.00000 0.02941 0.04874 = 0.03288 0.00420 -0.00376 0.00266 C11 1 0.336169 0.225098 0.280468 11.00000 0.03304 0.05518 = 0.03497 -0.01157 0.00849 0.00087 AFIX 13 H11 2 0.182769 0.241207 0.262898 11.00000 -1.20000 AFIX 0 C12 1 0.329309 0.173068 0.393891 11.00000 0.04953 0.04577 = 0.05138 -0.01474 0.00373 0.00594 AFIX 23 H12A 2 0.233489 0.107741 0.409390 11.00000 -1.20000 H12B 2 0.476646 0.147244 0.412234 11.00000 -1.20000 AFIX 0 C13 1 0.424188 0.144489 0.221193 11.00000 0.02814 0.05949 = 0.03911 -0.00647 -0.00366 -0.00090 C14 1 0.628972 0.093261 0.237951 11.00000 0.04745 0.06609 = 0.06236 -0.01325 0.00419 0.00020 AFIX 43 H14 2 0.721060 0.111294 0.283484 11.00000 -1.20000 AFIX 0 C15 1 0.693227 0.012049 0.182943 11.00000 0.07009 0.06358 = 0.09086 -0.02668 0.01085 0.01005 AFIX 43 H15 2 0.830478 -0.022665 0.192202 11.00000 -1.20000 AFIX 0 C16 1 0.560956 -0.015122 0.118639 11.00000 0.10912 0.05498 = 0.05575 -0.02162 0.02450 -0.02599 AFIX 43 H16 2 0.605143 -0.069772 0.085011 11.00000 -1.20000 AFIX 0 C17 1 0.359406 0.036949 0.101489 11.00000 0.08103 0.07694 = 0.06023 -0.01494 -0.01127 -0.01163 AFIX 43 H17 2 0.268767 0.018671 0.055538 11.00000 -1.20000 AFIX 0 C18 1 0.292217 0.117067 0.153326 11.00000 0.06101 0.04794 = 0.05981 -0.01427 0.00825 0.00778 AFIX 43 H18 2 0.156111 0.152418 0.141765 11.00000 -1.20000 AFIX 0 C19 1 0.196607 0.439450 0.479288 11.00000 0.04400 0.06587 = 0.04181 -0.00139 0.00048 0.00782 C20 1 0.698837 0.329964 0.283115 11.00000 0.03747 0.04686 = 0.06990 -0.00790 0.00017 -0.00592 C21 1 0.489298 0.394532 0.145645 11.00000 0.03792 0.04442 = 0.05459 -0.00654 0.00591 -0.00086 C22 1 0.309166 0.430747 0.076024 11.00000 0.05112 0.07870 = 0.05003 -0.00207 -0.00456 0.01054 AFIX 137 H22A 2 0.371869 0.462458 0.008836 11.00000 -1.50000 H22B 2 0.219457 0.486180 0.098322 11.00000 -1.50000 H22C 2 0.219635 0.367035 0.075872 11.00000 -1.50000 AFIX 0 C23 1 0.716625 0.686703 0.369185 11.00000 0.05086 0.08070 = 0.04328 -0.01219 0.00425 -0.01632 AFIX 43 H23 2 0.583768 0.650835 0.394950 11.00000 -1.20000 AFIX 0 C24 1 0.787968 0.690990 0.271679 11.00000 0.06767 0.06695 = 0.04325 -0.02310 -0.00039 -0.00118 AFIX 43 H24 2 0.703098 0.660243 0.230931 11.00000 -1.20000 AFIX 0 C25 1 0.984344 0.740694 0.234935 11.00000 0.05986 0.05915 = 0.04200 -0.01055 0.00567 0.00402 C26 1 1.112368 0.787423 0.293709 11.00000 0.05021 0.06262 = 0.03632 -0.00033 -0.00143 -0.00114 AFIX 43 H26 2 1.246945 0.821204 0.267661 11.00000 -1.20000 AFIX 0 C27 1 1.036263 0.782995 0.392460 11.00000 0.04353 0.06383 = 0.03717 -0.00839 0.00171 -0.00132 AFIX 43 H27 2 1.121649 0.813437 0.433229 11.00000 -1.20000 AFIX 0 C28 1 0.836276 0.734219 0.430985 11.00000 0.04220 0.04450 = 0.03917 -0.00335 0.00042 0.00191 C29 1 0.755958 0.728500 0.536036 11.00000 0.03546 0.05308 = 0.03429 -0.00638 0.00078 0.00454 C30 1 0.746172 0.817682 0.576791 11.00000 0.03137 0.04355 = 0.03771 -0.00182 0.00347 -0.00345 C31 1 0.661300 0.815331 0.679526 11.00000 0.03027 0.06219 = 0.04300 -0.01283 -0.00464 0.00896 C32 1 0.538777 0.708665 0.736229 11.00000 0.03047 0.05182 = 0.02981 -0.01031 -0.00240 -0.00070 C33 1 0.667400 0.607449 0.713334 11.00000 0.03029 0.05255 = 0.04786 -0.00439 -0.00587 -0.00095 AFIX 13 H33 2 0.818851 0.613259 0.732671 11.00000 -1.20000 AFIX 0 C34 1 0.682340 0.614883 0.599684 11.00000 0.04698 0.04523 = 0.04196 -0.00933 0.01554 -0.00579 AFIX 23 H34A 2 0.785422 0.558367 0.586162 11.00000 -1.20000 H34B 2 0.538546 0.597936 0.579847 11.00000 -1.20000 AFIX 0 C35 1 0.580687 0.492917 0.772969 11.00000 0.04707 0.05577 = 0.03949 -0.01322 0.01404 -0.00496 C36 1 0.380266 0.453163 0.752515 11.00000 0.05160 0.06209 = 0.06449 -0.01160 0.00535 -0.00186 AFIX 43 H36 2 0.294034 0.497793 0.704162 11.00000 -1.20000 AFIX 0 C37 1 0.308802 0.346011 0.804790 11.00000 0.09388 0.05985 = 0.06494 -0.00925 0.01733 -0.02984 AFIX 43 H37 2 0.172895 0.319474 0.792749 11.00000 -1.20000 AFIX 0 C38 1 0.438254 0.280702 0.873224 11.00000 0.12872 0.05722 = 0.06364 -0.00709 0.02290 -0.00012 AFIX 43 H38 2 0.393100 0.208138 0.906261 11.00000 -1.20000 AFIX 0 C39 1 0.637787 0.320971 0.894586 11.00000 0.11169 0.08570 = 0.04739 -0.00498 0.00172 0.01778 AFIX 43 H39 2 0.722714 0.276386 0.943535 11.00000 -1.20000 AFIX 0 C40 1 0.709588 0.425965 0.843835 11.00000 0.07620 0.05494 = 0.03882 -0.00167 0.00071 0.00741 AFIX 43 H40 2 0.844843 0.452193 0.857016 11.00000 -1.20000 AFIX 0 C41 1 0.306166 0.717957 0.705777 11.00000 0.05384 0.04997 = 0.05550 -0.01777 0.00552 0.00275 C42 1 0.501584 0.701428 0.847369 11.00000 0.05275 0.05124 = 0.04641 -0.01372 0.00403 -0.00446 C43 1 0.672111 0.694472 0.921184 11.00000 0.07009 0.08544 = 0.05605 -0.02664 -0.00658 0.00212 AFIX 137 H43A 2 0.602077 0.691805 0.986761 11.00000 -1.50000 H43B 2 0.766135 0.759336 0.900495 11.00000 -1.50000 H43C 2 0.758966 0.627751 0.924276 11.00000 -1.50000 AFIX 0 C44 1 0.810183 0.927403 0.516953 11.00000 0.04425 0.06764 = 0.04353 -0.01437 0.00057 -0.00415 N1 3 0.688187 0.409563 0.113921 11.00000 0.04738 0.09742 = 0.05713 0.00300 0.00313 -0.00638 N2 3 0.344885 0.520732 0.273724 11.00000 0.07895 0.05168 = 0.05912 -0.01455 0.00333 -0.00147 AFIX 3 H2A 2 0.289351 0.566660 0.306985 11.00000 -1.20000 AFIX 0 N3 3 0.152735 0.505615 0.523722 11.00000 0.08392 0.08721 = 0.06535 -0.03622 -0.00132 0.01651 N4 3 0.298188 0.701419 0.876842 11.00000 0.05089 0.10227 = 0.05728 -0.02110 0.00954 -0.00685 N5 3 0.667167 0.895621 0.723035 11.00000 0.07134 0.05041 = 0.05915 -0.01824 0.00059 -0.00233 AFIX 3 H5A 2 0.724969 0.958612 0.690055 11.00000 -1.20000 AFIX 0 N6 3 0.853151 1.016496 0.472395 11.00000 0.08161 0.06292 = 0.07605 -0.00840 -0.00637 -0.01253 O1 4 0.773698 0.296227 0.363856 11.00000 0.04147 0.08383 = 0.08009 -0.01853 -0.01882 0.00039 O2 4 0.825594 0.367717 0.198875 11.00000 0.03277 0.10858 = 0.08125 0.00879 0.00688 -0.00967 O3 4 0.236798 0.731273 0.624475 11.00000 0.04904 0.09185 = 0.06596 -0.02344 -0.01399 0.00147 O4 4 0.170596 0.712015 0.789098 11.00000 0.03821 0.12328 = 0.06568 -0.03620 0.00542 -0.00064 HKLF 4 REM 1_b.res in P1 REM R1 = 0.0433 for 3537 Fo > 4sig(Fo) and 0.1278 for all 6734 data REM 507 parameters refined using 3 restraints END WGHT 0.0000 0.0000 REM Highest difference peak 0.263, deepest hole -0.378, 1-sigma level 0.057 Q1 1 0.0758 0.2426 0.0899 11.00000 0.05 0.26 Q2 1 -0.0523 0.0775 0.9005 11.00000 0.05 0.25 Q3 1 -0.2662 0.3162 0.5930 11.00000 0.05 0.24 Q4 1 1.0692 0.6986 0.0990 11.00000 0.05 0.23 Q5 1 0.9102 0.5418 0.9070 11.00000 0.05 0.22 Q6 1 1.2678 0.7443 0.1025 11.00000 0.05 0.22 Q7 1 0.0129 -0.0224 0.8794 11.00000 0.05 0.20 Q8 1 0.6472 0.5500 0.0706 11.00000 0.05 0.19 Q9 1 0.4847 0.6201 0.9811 11.00000 0.05 0.19 Q10 1 -0.0022 0.1649 0.7412 11.00000 0.05 0.19 Q11 1 1.2445 0.8213 0.4526 11.00000 0.05 0.19 Q12 1 0.0039 0.1592 0.1283 11.00000 0.05 0.19 Q13 1 0.3916 0.3790 0.2872 11.00000 0.05 0.19 Q14 1 0.3655 -0.0945 0.8454 11.00000 0.05 0.19 Q15 1 0.7514 0.6233 1.0388 11.00000 0.05 0.19 Q16 1 0.6313 1.0183 0.4428 11.00000 0.05 0.18 Q17 1 1.0178 0.7514 -0.0227 11.00000 0.05 0.18 Q18 1 0.9156 1.0223 0.6618 11.00000 0.05 0.18 Q19 1 0.5517 0.7393 1.1038 11.00000 0.05 0.18 Q20 1 1.0454 0.6592 0.0224 11.00000 0.05 0.18 ; _shelx_res_checksum 51949 loop_ _space_group_symop_operation_xyz '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 -0.08018(15) 0.03289(8) 0.89326(7) 0.0891(4) Uani 1 1 d . . . . . Br2 Br 1.08449(12) 0.74783(7) 0.09944(6) 0.0710(4) Uani 1 1 d . . . . . C1 C -0.0346(13) 0.2285(7) 0.6006(6) 0.053(2) Uani 1 1 d . . . . . H1 H -0.1215 0.2822 0.5600 0.063 Uiso 1 1 calc R U . . . C2 C -0.1087(14) 0.1777(8) 0.6989(6) 0.059(2) Uani 1 1 d . . . . . H2 H -0.2460 0.1976 0.7236 0.070 Uiso 1 1 calc R U . . . C3 C 0.0153(18) 0.0994(9) 0.7601(7) 0.055(3) Uani 1 1 d . . . . . C4 C 0.2198(19) 0.0678(9) 0.7219(8) 0.065(3) Uani 1 1 d . . . . . H4 H 0.3056 0.0137 0.7628 0.078 Uiso 1 1 calc R U . . . C5 C 0.2941(18) 0.1175(9) 0.6230(8) 0.061(3) Uani 1 1 d . . . . . H5 H 0.4286 0.0955 0.5972 0.074 Uiso 1 1 calc R U . . . C6 C 0.1699(13) 0.1992(7) 0.5625(6) 0.046(2) Uani 1 1 d . . . . . C7 C 0.2502(11) 0.2502(7) 0.4576(5) 0.042(2) Uani 1 1 d . . . . . C8 C 0.2616(12) 0.3619(7) 0.4179(6) 0.041(2) Uani 1 1 d . . . . . C9 C 0.3440(12) 0.4167(8) 0.3166(6) 0.043(2) Uani 1 1 d . . . . . C10 C 0.4585(12) 0.3410(7) 0.2561(6) 0.039(2) Uani 1 1 d . . . . . C11 C 0.3362(13) 0.2251(7) 0.2805(6) 0.041(2) Uani 1 1 d . . . . . H11 H 0.1828 0.2412 0.2629 0.050 Uiso 1 1 calc R U . . . C12 C 0.3293(16) 0.1731(8) 0.3939(7) 0.049(3) Uani 1 1 d . . . . . H12A H 0.2335 0.1077 0.4094 0.059 Uiso 1 1 calc R U . . . H12B H 0.4766 0.1472 0.4122 0.059 Uiso 1 1 calc R U . . . C13 C 0.4242(13) 0.1445(7) 0.2212(6) 0.043(2) Uani 1 1 d . . . . . C14 C 0.6290(16) 0.0933(8) 0.2380(7) 0.059(3) Uani 1 1 d . . . . . H14 H 0.7211 0.1113 0.2835 0.071 Uiso 1 1 calc R U . . . C15 C 0.6932(18) 0.0120(9) 0.1829(9) 0.074(3) Uani 1 1 d . . . . . H15 H 0.8305 -0.0227 0.1922 0.089 Uiso 1 1 calc R U . . . C16 C 0.561(2) -0.0151(8) 0.1186(8) 0.073(3) Uani 1 1 d . . . . . H16 H 0.6051 -0.0698 0.0850 0.087 Uiso 1 1 calc R U . . . C17 C 0.359(2) 0.0369(10) 0.1015(8) 0.073(3) Uani 1 1 d . . . . . H17 H 0.2688 0.0187 0.0555 0.087 Uiso 1 1 calc R U . . . C18 C 0.2922(15) 0.1171(7) 0.1533(7) 0.057(2) Uani 1 1 d . . . . . H18 H 0.1561 0.1524 0.1418 0.068 Uiso 1 1 calc R U . . . C19 C 0.1966(13) 0.4395(8) 0.4793(6) 0.053(2) Uani 1 1 d . . . . . C20 C 0.6988(15) 0.3300(8) 0.2831(8) 0.053(2) Uani 1 1 d . . . . . C21 C 0.4893(15) 0.3945(7) 0.1456(6) 0.047(2) Uani 1 1 d . . . . . C22 C 0.3092(15) 0.4307(9) 0.0760(7) 0.062(3) Uani 1 1 d . . . . . H22A H 0.3719 0.4625 0.0088 0.094 Uiso 1 1 calc R U . . . H22B H 0.2195 0.4862 0.0983 0.094 Uiso 1 1 calc R U . . . H22C H 0.2196 0.3670 0.0759 0.094 Uiso 1 1 calc R U . . . C23 C 0.7166(16) 0.6867(8) 0.3692(8) 0.059(3) Uani 1 1 d . . . . . H23 H 0.5838 0.6508 0.3949 0.071 Uiso 1 1 calc R U . . . C24 C 0.7880(18) 0.6910(8) 0.2717(8) 0.058(3) Uani 1 1 d . . . . . H24 H 0.7031 0.6602 0.2309 0.069 Uiso 1 1 calc R U . . . C25 C 0.9843(17) 0.7407(8) 0.2349(7) 0.054(3) Uani 1 1 d . . . . . C26 C 1.1124(14) 0.7874(7) 0.2937(6) 0.052(2) Uani 1 1 d . . . . . H26 H 1.2469 0.8212 0.2677 0.062 Uiso 1 1 calc R U . . . C27 C 1.0363(13) 0.7830(7) 0.3925(6) 0.049(2) Uani 1 1 d . . . . . H27 H 1.1216 0.8134 0.4332 0.059 Uiso 1 1 calc R U . . . C28 C 0.8363(13) 0.7342(6) 0.4310(6) 0.043(2) Uani 1 1 d . . . . . C29 C 0.7560(11) 0.7285(7) 0.5360(5) 0.042(2) Uani 1 1 d . . . . . C30 C 0.7462(11) 0.8177(7) 0.5768(6) 0.0392(19) Uani 1 1 d . . . . . C31 C 0.6613(12) 0.8153(7) 0.6795(6) 0.045(2) Uani 1 1 d . . . . . C32 C 0.5388(13) 0.7087(7) 0.7362(6) 0.037(2) Uani 1 1 d . . . . . C33 C 0.6674(13) 0.6074(7) 0.7133(6) 0.045(2) Uani 1 1 d . . . . . H33 H 0.8189 0.6133 0.7327 0.054 Uiso 1 1 calc R U . . . C34 C 0.6823(15) 0.6149(7) 0.5997(7) 0.046(2) Uani 1 1 d . . . . . H34A H 0.7854 0.5584 0.5862 0.055 Uiso 1 1 calc R U . . . H34B H 0.5385 0.5979 0.5798 0.055 Uiso 1 1 calc R U . . . C35 C 0.5807(14) 0.4929(7) 0.7730(6) 0.048(2) Uani 1 1 d . . . . . C36 C 0.3803(16) 0.4532(8) 0.7525(7) 0.060(3) Uani 1 1 d . . . . . H36 H 0.2940 0.4978 0.7042 0.073 Uiso 1 1 calc R U . . . C37 C 0.3088(19) 0.3460(9) 0.8048(8) 0.075(3) Uani 1 1 d . . . . . H37 H 0.1729 0.3195 0.7927 0.090 Uiso 1 1 calc R U . . . C38 C 0.438(2) 0.2807(10) 0.8732(8) 0.086(3) Uani 1 1 d . . . . . H38 H 0.3931 0.2081 0.9063 0.103 Uiso 1 1 calc R U . . . C39 C 0.638(2) 0.3210(11) 0.8946(8) 0.084(4) Uani 1 1 d . . . . . H39 H 0.7227 0.2764 0.9435 0.101 Uiso 1 1 calc R U . . . C40 C 0.7096(17) 0.4260(8) 0.8438(6) 0.059(2) Uani 1 1 d . . . . . H40 H 0.8448 0.4522 0.8570 0.070 Uiso 1 1 calc R U . . . C41 C 0.3062(16) 0.7180(7) 0.7058(8) 0.053(3) Uani 1 1 d . . . . . C42 C 0.5016(15) 0.7014(7) 0.8474(6) 0.050(2) Uani 1 1 d . . . . . C43 C 0.6721(16) 0.6945(8) 0.9212(7) 0.069(3) Uani 1 1 d . . . . . H43A H 0.6021 0.6918 0.9868 0.103 Uiso 1 1 calc R U . . . H43B H 0.7661 0.7593 0.9005 0.103 Uiso 1 1 calc R U . . . H43C H 0.7590 0.6278 0.9243 0.103 Uiso 1 1 calc R U . . . C44 C 0.8102(13) 0.9274(9) 0.5170(6) 0.052(2) Uani 1 1 d . . . . . N1 N 0.6882(13) 0.4096(7) 0.1139(6) 0.071(2) Uani 1 1 d . . . . . N2 N 0.3449(12) 0.5207(6) 0.2737(5) 0.063(2) Uani 1 1 d . . . . . H2A H 0.2894 0.5667 0.3070 0.076 Uiso 1 1 d R U . . . N3 N 0.1527(13) 0.5056(7) 0.5237(6) 0.076(2) Uani 1 1 d . . . . . N4 N 0.2982(14) 0.7014(7) 0.8768(6) 0.070(2) Uani 1 1 d . . . . . N5 N 0.6672(11) 0.8956(6) 0.7230(5) 0.0597(19) Uani 1 1 d . . . . . H5A H 0.7250 0.9586 0.6901 0.072 Uiso 1 1 d R U . . . N6 N 0.8532(13) 1.0165(7) 0.4724(6) 0.075(3) Uani 1 1 d . . . . . O1 O 0.7737(9) 0.2962(5) 0.3639(5) 0.0681(18) Uani 1 1 d . . . . . O2 O 0.8256(9) 0.3677(6) 0.1989(5) 0.080(2) Uani 1 1 d . . . . . O3 O 0.2368(9) 0.7313(5) 0.6245(5) 0.0678(17) Uani 1 1 d . . . . . O4 O 0.1706(10) 0.7120(6) 0.7891(5) 0.0738(19) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1195(11) 0.0953(9) 0.0453(7) -0.0062(6) 0.0113(7) -0.0261(7) Br2 0.0859(8) 0.0831(8) 0.0418(6) -0.0146(5) 0.0075(5) 0.0021(6) C1 0.044(6) 0.063(6) 0.050(6) -0.016(5) 0.003(4) 0.003(4) C2 0.050(6) 0.085(7) 0.044(6) -0.025(5) 0.012(5) -0.014(5) C3 0.062(7) 0.065(7) 0.039(6) -0.016(5) 0.002(5) -0.012(6) C4 0.077(8) 0.062(7) 0.049(8) 0.001(6) -0.016(6) -0.005(6) C5 0.068(7) 0.061(7) 0.049(7) -0.007(6) 0.008(6) 0.013(6) C6 0.043(6) 0.049(6) 0.045(5) -0.012(5) 0.004(4) -0.003(4) C7 0.035(5) 0.054(6) 0.034(5) -0.006(4) -0.003(4) -0.003(4) C8 0.030(5) 0.053(6) 0.045(5) -0.020(5) 0.002(4) 0.004(4) C9 0.029(5) 0.053(6) 0.046(5) -0.012(5) 0.003(4) 0.001(4) C10 0.029(5) 0.049(6) 0.033(5) 0.004(4) -0.004(4) 0.003(4) C11 0.033(5) 0.055(6) 0.035(5) -0.012(5) 0.008(4) 0.001(4) C12 0.050(6) 0.046(6) 0.051(7) -0.015(5) 0.004(5) 0.006(5) C13 0.028(5) 0.059(6) 0.039(6) -0.006(5) -0.004(4) -0.001(5) C14 0.047(7) 0.066(7) 0.062(7) -0.013(5) 0.004(5) 0.000(5) C15 0.070(8) 0.064(7) 0.091(9) -0.027(7) 0.011(7) 0.010(6) C16 0.109(10) 0.055(7) 0.056(7) -0.022(5) 0.025(6) -0.026(7) C17 0.081(9) 0.077(8) 0.060(7) -0.015(6) -0.011(6) -0.012(7) C18 0.061(6) 0.048(6) 0.060(6) -0.014(5) 0.008(5) 0.008(5) C19 0.044(6) 0.066(7) 0.042(6) -0.001(5) 0.000(4) 0.008(5) C20 0.037(6) 0.047(6) 0.070(8) -0.008(5) 0.000(6) -0.006(4) C21 0.038(6) 0.044(6) 0.055(6) -0.007(5) 0.006(5) -0.001(4) C22 0.051(6) 0.079(7) 0.050(6) -0.002(5) -0.005(5) 0.011(5) C23 0.051(6) 0.081(8) 0.043(7) -0.012(6) 0.004(5) -0.016(5) C24 0.068(7) 0.067(7) 0.043(7) -0.023(5) 0.000(6) -0.001(6) C25 0.060(7) 0.059(6) 0.042(6) -0.011(5) 0.006(5) 0.004(5) C26 0.050(6) 0.063(6) 0.036(5) 0.000(4) -0.001(4) -0.001(5) C27 0.044(6) 0.064(6) 0.037(5) -0.008(4) 0.002(4) -0.001(5) C28 0.042(5) 0.045(5) 0.039(5) -0.003(4) 0.000(4) 0.002(4) C29 0.035(5) 0.053(6) 0.034(5) -0.006(4) 0.001(4) 0.005(4) C30 0.031(5) 0.044(5) 0.038(5) -0.002(4) 0.003(4) -0.003(4) C31 0.030(5) 0.062(6) 0.043(5) -0.013(5) -0.005(4) 0.009(4) C32 0.030(5) 0.052(6) 0.030(5) -0.010(4) -0.002(4) -0.001(4) C33 0.030(5) 0.053(6) 0.048(6) -0.004(5) -0.006(4) -0.001(4) C34 0.047(6) 0.045(6) 0.042(6) -0.009(5) 0.016(4) -0.006(4) C35 0.047(6) 0.056(6) 0.039(6) -0.013(5) 0.014(5) -0.005(5) C36 0.052(7) 0.062(7) 0.064(7) -0.012(6) 0.005(5) -0.002(6) C37 0.094(9) 0.060(8) 0.065(7) -0.009(6) 0.017(7) -0.030(7) C38 0.129(11) 0.057(7) 0.064(8) -0.007(6) 0.023(8) 0.000(8) C39 0.112(11) 0.086(10) 0.047(7) -0.005(7) 0.002(7) 0.018(8) C40 0.076(7) 0.055(6) 0.039(5) -0.002(5) 0.001(5) 0.007(5) C41 0.054(7) 0.050(6) 0.056(7) -0.018(5) 0.006(6) 0.003(5) C42 0.053(6) 0.051(6) 0.046(6) -0.014(4) 0.004(5) -0.004(5) C43 0.070(7) 0.085(8) 0.056(7) -0.027(6) -0.007(5) 0.002(6) C44 0.044(5) 0.068(7) 0.044(5) -0.014(5) 0.001(4) -0.004(5) N1 0.047(5) 0.097(7) 0.057(5) 0.003(5) 0.003(5) -0.006(5) N2 0.079(6) 0.052(5) 0.059(5) -0.015(4) 0.003(4) -0.001(4) N3 0.084(6) 0.087(6) 0.065(6) -0.036(5) -0.001(4) 0.017(5) N4 0.051(5) 0.102(7) 0.057(5) -0.021(5) 0.010(4) -0.007(5) N5 0.071(5) 0.050(5) 0.059(5) -0.018(4) 0.001(4) -0.002(4) N6 0.082(6) 0.063(6) 0.076(6) -0.008(5) -0.006(5) -0.013(5) O1 0.041(4) 0.084(5) 0.080(5) -0.019(4) -0.019(3) 0.000(3) O2 0.033(4) 0.109(6) 0.081(5) 0.009(4) 0.007(4) -0.010(3) O3 0.049(4) 0.092(5) 0.066(5) -0.023(4) -0.014(3) 0.001(3) O4 0.038(4) 0.123(6) 0.066(5) -0.036(4) 0.005(4) -0.001(4) 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C1 C6 120.0(8) . . ? C2 C1 H1 120.0 . . ? C6 C1 H1 120.0 . . ? C3 C2 C1 121.3(8) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 119.2(9) . . ? C2 C3 Br1 121.6(8) . . ? C4 C3 Br1 119.2(8) . . ? C5 C4 C3 119.8(10) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 120.4(10) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.2(8) . . ? C5 C6 C7 119.7(8) . . ? C1 C6 C7 121.0(7) . . ? C8 C7 C6 123.3(7) . . ? C8 C7 C12 119.0(7) . . ? C6 C7 C12 117.7(7) . . ? C7 C8 C9 125.8(7) . . ? C7 C8 C19 120.5(7) . . ? C9 C8 C19 113.6(7) . . ? N2 C9 C8 128.1(8) . . ? N2 C9 C10 115.8(7) . . ? C8 C9 C10 115.9(7) . . ? C21 C10 C20 99.8(7) . . ? C21 C10 C9 113.6(6) . . ? C20 C10 C9 107.3(7) . . ? C21 C10 C11 113.3(7) . . ? C20 C10 C11 112.8(6) . . ? C9 C10 C11 109.6(6) . . ? C13 C11 C12 111.8(7) . . ? C13 C11 C10 115.1(6) . . ? C12 C11 C10 109.3(7) . . ? C13 C11 H11 106.7 . . ? C12 C11 H11 106.7 . . ? C10 C11 H11 106.7 . . ? C7 C12 C11 114.6(7) . . ? C7 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? C7 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C18 C13 C14 120.1(8) . . ? C18 C13 C11 118.3(7) . . ? C14 C13 C11 121.5(8) . . ? C13 C14 C15 117.7(9) . . ? C13 C14 H14 121.1 . . ? C15 C14 H14 121.1 . . ? C16 C15 C14 121.4(10) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 120.6(10) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 119.5(10) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C13 C18 C17 120.7(9) . . ? C13 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? N3 C19 C8 175.9(9) . . ? O1 C20 O2 122.4(9) . . ? O1 C20 C10 129.4(9) . . ? O2 C20 C10 108.3(8) . . ? N1 C21 C10 113.7(7) . . ? N1 C21 C22 120.7(8) . . ? C10 C21 C22 125.6(8) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 121.9(9) . . ? C24 C23 H23 119.1 . . ? C28 C23 H23 119.1 . . ? C25 C24 C23 119.1(10) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 121.5(8) . . ? C24 C25 Br2 119.5(8) . . ? C26 C25 Br2 119.0(7) . . ? C25 C26 C27 118.6(8) . . ? C25 C26 H26 120.7 . . ? C27 C26 H26 120.7 . . ? C28 C27 C26 120.9(8) . . ? C28 C27 H27 119.5 . . ? C26 C27 H27 119.5 . . ? C27 C28 C23 118.0(8) . . ? C27 C28 C29 121.1(7) . . ? C23 C28 C29 120.9(7) . . ? C30 C29 C28 123.8(7) . . ? C30 C29 C34 119.5(7) . . ? C28 C29 C34 116.7(7) . . ? C29 C30 C44 120.6(7) . . ? C29 C30 C31 125.1(7) . . ? C44 C30 C31 114.3(7) . . ? N5 C31 C30 126.5(8) . . ? N5 C31 C32 117.6(7) . . ? C30 C31 C32 115.7(7) . . ? C41 C32 C42 100.3(7) . . ? C41 C32 C31 108.3(6) . . ? C42 C32 C31 112.4(6) . . ? C41 C32 C33 114.5(7) . . ? C42 C32 C33 113.4(7) . . ? C31 C32 C33 107.9(6) . . ? C35 C33 C34 110.8(7) . . ? C35 C33 C32 114.8(7) . . ? C34 C33 C32 110.7(6) . . ? C35 C33 H33 106.7 . . ? C34 C33 H33 106.7 . . ? C32 C33 H33 106.7 . . ? C29 C34 C33 113.4(7) . . ? C29 C34 H34A 108.9 . . ? C33 C34 H34A 108.9 . . ? C29 C34 H34B 108.9 . . ? C33 C34 H34B 108.9 . . ? H34A C34 H34B 107.7 . . ? C40 C35 C36 120.0(9) . . ? C40 C35 C33 119.3(8) . . ? C36 C35 C33 120.6(8) . . ? C37 C36 C35 119.6(10) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C38 C37 C36 119.7(11) . . ? C38 C37 H37 120.2 . . ? C36 C37 H37 120.2 . . ? C37 C38 C39 120.7(11) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C40 C39 C38 120.2(11) . . ? C40 C39 H39 119.9 . . ? C38 C39 H39 119.9 . . ? C39 C40 C35 119.8(11) . . ? C39 C40 H40 120.1 . . ? C35 C40 H40 120.1 . . ? O3 C41 O4 121.7(9) . . ? O3 C41 C32 129.9(8) . . ? O4 C41 C32 108.4(9) . . ? N4 C42 C43 119.6(8) . . ? N4 C42 C32 113.3(8) . . ? C43 C42 C32 127.1(8) . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? N6 C44 C30 176.6(9) . . ? C21 N1 O2 108.3(7) . . ? C9 N2 H2A 118.5 . . ? C42 N4 O4 107.6(7) . . ? C31 N5 H5A 118.9 . . ? C20 O2 N1 109.9(7) . . ? C41 O4 N4 110.2(7) . . ? 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 Br1 C3 1.859(9) . ? Br2 C25 1.893(9) . ? C1 C2 1.381(10) . ? C1 C6 1.390(10) . ? C1 H1 0.9300 . ? C2 C3 1.359(12) . ? C2 H2 0.9300 . ? C3 C4 1.401(14) . ? C4 C5 1.387(13) . ? C4 H4 0.9300 . ? C5 C6 1.378(12) . ? C5 H5 0.9300 . ? C6 C7 1.470(10) . ? C7 C8 1.345(10) . ? C7 C12 1.491(11) . ? C8 C9 1.442(11) . ? C8 C19 1.452(13) . ? C9 N2 1.266(9) . ? C9 C10 1.522(11) . ? C10 C21 1.490(10) . ? C10 C20 1.521(12) . ? C10 C11 1.567(11) . ? C11 C13 1.499(11) . ? C11 C12 1.521(11) . ? C11 H11 0.9800 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.368(11) . ? C13 C14 1.389(11) . ? C14 C15 1.426(13) . ? C14 H14 0.9300 . ? C15 C16 1.331(14) . ? C15 H15 0.9300 . ? C16 C17 1.376(15) . ? C16 H16 0.9300 . ? C17 C18 1.390(13) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 N3 1.148(10) . ? C20 O1 1.194(10) . ? C20 O2 1.328(10) . ? C21 N1 1.256(10) . ? C21 C22 1.484(12) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.363(12) . ? C23 C28 1.385(12) . ? C23 H23 0.9300 . ? C24 C25 1.355(13) . ? C24 H24 0.9300 . ? C25 C26 1.378(12) . ? C26 C27 1.386(10) . ? C26 H26 0.9300 . ? C27 C28 1.375(10) . ? C27 H27 0.9300 . ? C28 C29 1.471(10) . ? C29 C30 1.345(10) . ? C29 C34 1.507(11) . ? C30 C44 1.436(12) . ? C30 C31 1.458(10) . ? C31 N5 1.274(9) . ? C31 C32 1.524(11) . ? C32 C41 1.490(12) . ? C32 C42 1.502(11) . ? C32 C33 1.543(11) . ? C33 C35 1.523(11) . ? C33 C34 1.530(10) . ? C33 H33 0.9800 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C40 1.380(11) . ? C35 C36 1.387(12) . ? C36 C37 1.393(12) . ? C36 H36 0.9300 . ? C37 C38 1.354(15) . ? C37 H37 0.9300 . ? C38 C39 1.389(16) . ? C38 H38 0.9300 . ? C39 C40 1.367(14) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C41 O3 1.185(10) . ? C41 O4 1.348(10) . ? C42 N4 1.272(10) . ? C42 C43 1.477(12) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 N6 1.137(10) . ? N1 O2 1.456(9) . ? N2 H2A 0.8600 . ? N4 O4 1.446(10) . ? N5 H5A 0.8600 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.4(13) . . . . ? C1 C2 C3 C4 -1.5(14) . . . . ? C1 C2 C3 Br1 178.7(6) . . . . ? C2 C3 C4 C5 0.7(14) . . . . ? Br1 C3 C4 C5 -179.4(8) . . . . ? C3 C4 C5 C6 1.2(15) . . . . ? C4 C5 C6 C1 -2.3(14) . . . . ? C4 C5 C6 C7 -179.4(8) . . . . ? C2 C1 C6 C5 1.6(13) . . . . ? C2 C1 C6 C7 178.6(7) . . . . ? C5 C6 C7 C8 -129.6(9) . . . . ? C1 C6 C7 C8 53.4(11) . . . . ? C5 C6 C7 C12 48.3(11) . . . . ? C1 C6 C7 C12 -128.7(9) . . . . ? C6 C7 C8 C9 178.3(7) . . . . ? C12 C7 C8 C9 0.4(11) . . . . ? C6 C7 C8 C19 1.0(11) . . . . ? C12 C7 C8 C19 -176.8(7) . . . . ? C7 C8 C9 N2 174.9(8) . . . . ? C19 C8 C9 N2 -7.7(12) . . . . ? C7 C8 C9 C10 -9.7(11) . . . . ? C19 C8 C9 C10 167.7(7) . . . . ? N2 C9 C10 C21 -18.6(10) . . . . ? C8 C9 C10 C21 165.4(7) . . . . ? N2 C9 C10 C20 90.7(8) . . . . ? C8 C9 C10 C20 -85.3(8) . . . . ? N2 C9 C10 C11 -146.5(7) . . . . ? C8 C9 C10 C11 37.5(9) . . . . ? C21 C10 C11 C13 48.6(9) . . . . ? C20 C10 C11 C13 -63.9(9) . . . . ? C9 C10 C11 C13 176.6(7) . . . . ? C21 C10 C11 C12 175.5(7) . . . . ? C20 C10 C11 C12 63.0(9) . . . . ? C9 C10 C11 C12 -56.5(8) . . . . ? C8 C7 C12 C11 -21.6(11) . . . . ? C6 C7 C12 C11 160.4(7) . . . . ? C13 C11 C12 C7 178.1(7) . . . . ? C10 C11 C12 C7 49.3(9) . . . . ? C12 C11 C13 C18 120.9(9) . . . . ? C10 C11 C13 C18 -113.5(8) . . . . ? C12 C11 C13 C14 -55.5(10) . . . . ? C10 C11 C13 C14 70.1(10) . . . . ? C18 C13 C14 C15 -0.4(13) . . . . ? C11 C13 C14 C15 175.9(8) . . . . ? C13 C14 C15 C16 -0.9(14) . . . . ? C14 C15 C16 C17 1.7(16) . . . . ? C15 C16 C17 C18 -1.2(15) . . . . ? C14 C13 C18 C17 0.9(13) . . . . ? C11 C13 C18 C17 -175.5(8) . . . . ? C16 C17 C18 C13 -0.1(14) . . . . ? C21 C10 C20 O1 176.6(9) . . . . ? C9 C10 C20 O1 57.9(12) . . . . ? C11 C10 C20 O1 -62.9(12) . . . . ? C21 C10 C20 O2 -2.1(9) . . . . ? C9 C10 C20 O2 -120.8(8) . . . . ? C11 C10 C20 O2 118.4(8) . . . . ? C20 C10 C21 N1 1.1(9) . . . . ? C9 C10 C21 N1 115.0(8) . . . . ? C11 C10 C21 N1 -119.1(8) . . . . ? C20 C10 C21 C22 -177.6(9) . . . . ? C9 C10 C21 C22 -63.7(11) . . . . ? C11 C10 C21 C22 62.2(11) . . . . ? C28 C23 C24 C25 1.7(15) . . . . ? C23 C24 C25 C26 -0.4(15) . . . . ? C23 C24 C25 Br2 -179.7(7) . . . . ? C24 C25 C26 C27 -0.1(13) . . . . ? Br2 C25 C26 C27 179.2(6) . . . . ? C25 C26 C27 C28 -0.7(12) . . . . ? C26 C27 C28 C23 1.9(12) . . . . ? C26 C27 C28 C29 179.5(7) . . . . ? C24 C23 C28 C27 -2.5(14) . . . . ? C24 C23 C28 C29 -180.0(8) . . . . ? C27 C28 C29 C30 51.1(10) . . . . ? C23 C28 C29 C30 -131.5(9) . . . . ? C27 C28 C29 C34 -128.7(8) . . . . ? C23 C28 C29 C34 48.7(10) . . . . ? C28 C29 C30 C44 1.8(11) . . . . ? C34 C29 C30 C44 -178.4(7) . . . . ? C28 C29 C30 C31 178.0(7) . . . . ? C34 C29 C30 C31 -2.2(11) . . . . ? C29 C30 C31 N5 173.6(7) . . . . ? C44 C30 C31 N5 -10.0(11) . . . . ? C29 C30 C31 C32 -11.4(10) . . . . ? C44 C30 C31 C32 165.1(6) . . . . ? N5 C31 C32 C41 92.6(8) . . . . ? C30 C31 C32 C41 -82.9(8) . . . . ? N5 C31 C32 C42 -17.3(10) . . . . ? C30 C31 C32 C42 167.2(7) . . . . ? N5 C31 C32 C33 -143.0(7) . . . . ? C30 C31 C32 C33 41.5(8) . . . . ? C41 C32 C33 C35 -65.5(9) . . . . ? C42 C32 C33 C35 48.8(10) . . . . ? C31 C32 C33 C35 173.9(7) . . . . ? C41 C32 C33 C34 60.8(9) . . . . ? C42 C32 C33 C34 175.1(7) . . . . ? C31 C32 C33 C34 -59.8(8) . . . . ? C30 C29 C34 C33 -17.0(10) . . . . ? C28 C29 C34 C33 162.8(7) . . . . ? C35 C33 C34 C29 177.0(7) . . . . ? C32 C33 C34 C29 48.5(9) . . . . ? C34 C33 C35 C40 120.5(8) . . . . ? C32 C33 C35 C40 -113.1(8) . . . . ? C34 C33 C35 C36 -55.7(10) . . . . ? C32 C33 C35 C36 70.6(10) . . . . ? C40 C35 C36 C37 0.8(13) . . . . ? C33 C35 C36 C37 177.1(8) . . . . ? C35 C36 C37 C38 -1.6(15) . . . . ? C36 C37 C38 C39 2.4(16) . . . . ? C37 C38 C39 C40 -2.4(17) . . . . ? C38 C39 C40 C35 1.5(15) . . . . ? C36 C35 C40 C39 -0.8(13) . . . . ? C33 C35 C40 C39 -177.1(8) . . . . ? C42 C32 C41 O3 176.1(9) . . . . ? C31 C32 C41 O3 58.2(12) . . . . ? C33 C32 C41 O3 -62.1(12) . . . . ? C42 C32 C41 O4 -2.0(8) . . . . ? C31 C32 C41 O4 -119.9(7) . . . . ? C33 C32 C41 O4 119.7(8) . . . . ? C41 C32 C42 N4 2.3(9) . . . . ? C31 C32 C42 N4 117.1(8) . . . . ? C33 C32 C42 N4 -120.2(8) . . . . ? C41 C32 C42 C43 -177.8(8) . . . . ? C31 C32 C42 C43 -63.0(11) . . . . ? C33 C32 C42 C43 59.6(11) . . . . ? C10 C21 N1 O2 0.2(10) . . . . ? C22 C21 N1 O2 179.0(8) . . . . ? C43 C42 N4 O4 178.4(8) . . . . ? C32 C42 N4 O4 -1.7(10) . . . . ? O1 C20 O2 N1 -176.4(8) . . . . ? C10 C20 O2 N1 2.4(10) . . . . ? C21 N1 O2 C20 -1.7(10) . . . . ? O3 C41 O4 N4 -177.1(8) . . . . ? C32 C41 O4 N4 1.3(9) . . . . ? C42 N4 O4 C41 0.2(10) . . . . ?