#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:05:58 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288809 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247625.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_7247625 loop_ _publ_author_name 'Wood, Oskar G.' 'Jones, Leanne' 'Hawes, Chris S.' _publ_section_title ; Supporting coordination through hydrogen bonding in lanthanide complexes of 7-azaindole-N-oxide ; _journal_issue 45 _journal_name_full CrystEngComm _journal_page_first 6371 _journal_page_last 6378 _journal_paper_doi 10.1039/D3CE00985H _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C42 H36 Cl6 Eu2 N12 O6' _chemical_formula_sum 'C42 H36 Cl6 Eu2 N12 O6' _chemical_formula_weight 1321.45 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2023-08-02 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2023-08-10 deposited with the CCDC. 2023-11-01 downloaded from the CCDC. ; _cell_angle_alpha 79.1160(10) _cell_angle_beta 80.1310(10) _cell_angle_gamma 79.9150(10) _cell_formula_units_Z 1 _cell_length_a 8.4097(3) _cell_length_b 10.7232(4) _cell_length_c 13.8568(5) _cell_measurement_reflns_used 9966 _cell_measurement_temperature 150.00 _cell_measurement_theta_max 28.223 _cell_measurement_theta_min 2.486 _cell_volume 1195.72(8) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 150.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 Quest ECO' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_unetI/netI 0.0379 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 26086 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.335 _diffrn_reflns_theta_min 2.661 _diffrn_source_current 20.0 _diffrn_source_power 1.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.994 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6910 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0592 before and 0.0525 after correction. The Ratio of minimum to maximum transmission is 0.9266. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.835 _exptl_crystal_description block _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _refine_diff_density_max 2.124 _refine_diff_density_min -1.364 _refine_diff_density_rms 0.118 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 394 _refine_ls_number_reflns 5964 _refine_ls_number_restraints 174 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0331 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0113P)^2^+3.0433P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.0644 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5114 _reflns_number_total 5964 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00985h2.cif _cod_data_source_block 4 _cod_depositor_comments 'Adding full bibliography for 7247622--7247628.cif.' _cod_database_code 7247625 _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_max 0.796 _shelx_estimated_absorpt_t_min 0.646 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups 2. Restrained distances N4-H4 = N2-H2 0.88 with sigma of 0.02 N7-C22 \\sim N7-C26 \\sim N5-C19 \\sim N5-C15 \\sim N6-C19 \\sim N8-C26 with sigma of 0.02 N8-C28 \\sim N6-C21 with sigma of 0.02 C19-C18 \\sim C25-C26 with sigma of 0.02 C27-C25 \\sim C20-C18 with sigma of 0.02 C16-C15 \\sim C17-C16 \\sim C17-C18 \\sim C23-C22 \\sim C23-C24 \\sim C25-C24 with sigma of 0.02 C20-C21 \\sim C27-C28 with sigma of 0.02 3. Rigid body (RIGU) restrains N5, N6, C15, C16, C17, C18, C19, C20, C21, N7, N8, C22, C23, C24, C25, C26, C27, C28 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 4. Others Fixed Sof: N5(0.5) N6(0.5) H6A(0.5) C15(0.5) H15(0.5) C16(0.5) H16(0.5) C17(0.5) H17(0.5) C18(0.5) C19(0.5) C20(0.5) H20(0.5) C21(0.5) H21(0.5) N7(0.5) N8(0.5) H8A(0.5) C22(0.5) H22(0.5) C23(0.5) H23(0.5) C24(0.5) H24(0.5) C25(0.5) C26(0.5) C27(0.5) H27(0.5) C28(0.5) H28(0.5) 5.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2A), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), N6(H6A), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), N8(H8A), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28) ; _shelx_res_file ; TITL ow5aw_0m_a.res in P-1 ow5aw_0m.res created by SHELXL-2018/3 at 14:06:02 on 02-Aug-2023 REM Old TITL OW5AW_0m in P-1 REM SHELXT solution in P-1 REM R1 0.159, Rweak 0.012, Alpha 0.038, Orientation as input REM Formula found by SHELXT: C24 N8 O4 Eu CELL 0.71073 8.4097 10.7232 13.8568 79.116 80.131 79.915 ZERR 1 0.0003 0.0004 0.0005 0.001 0.001 0.001 LATT 1 SFAC C H Cl Eu N O UNIT 42 36 6 2 12 6 EQIV $1 1-X,1-Y,1-Z RIGU 0.001 0.001 N5 > C28 SADI N7 C22 N7 C26 N5 C19 N5 C15 N6 C19 N8 C26 SADI N8 C28 N6 C21 SADI C19 C18 C25 C26 SADI C27 C25 C20 C18 SADI C16 C15 C17 C16 C17 C18 C23 C22 C23 C24 C25 C24 SADI C20 C21 C27 C28 DFIX 0.88 N4 H4 N2 H2 L.S. 4 PLAN 20 SIZE 0.08 0.1 0.16 TEMP -123.15 CONF HTAB N2 Cl2 HTAB N4 Cl2 HTAB N6 Cl1_$1 HTAB N8 Cl1 HTAB N8 Cl2_$1 BOND $H list 4 MORE -1 fmap 2 acta OMIT 1 0 0 OMIT 0 1 1 OMIT 1 1 0 REM REM REM WGHT 0.011300 3.043300 FVAR 0.40776 EU1 4 0.544337 0.582875 0.346869 11.00000 0.02766 0.02635 = 0.01270 -0.00290 -0.00088 0.00376 CL1 3 0.797704 0.658980 0.401879 11.00000 0.05729 0.09971 = 0.03488 -0.00331 -0.01684 -0.03553 CL2 3 0.293493 0.488251 0.302607 11.00000 0.03886 0.05060 = 0.04154 -0.00022 -0.00889 -0.01381 CL3 3 0.639050 0.688552 0.156674 11.00000 0.03561 0.03188 = 0.01668 -0.00311 0.00003 -0.00216 O1 6 0.704624 0.415986 0.283077 11.00000 0.04852 0.03707 = 0.01483 -0.00530 0.00302 0.00939 O2 6 0.383292 0.783552 0.336824 11.00000 0.04466 0.03052 = 0.01851 -0.00094 -0.00277 0.00932 O3 6 0.409646 0.601272 0.514419 11.00000 0.04678 0.03018 = 0.01822 -0.00125 0.00685 0.01720 N1 5 0.804207 0.394022 0.198578 11.00000 0.04032 0.02946 = 0.02840 -0.00296 -0.00231 0.00321 N2 5 0.575601 0.371718 0.125857 11.00000 0.02982 0.02927 = 0.02506 -0.00397 0.00132 -0.00817 H2 2 0.496510 0.388549 0.174714 11.00000 -1.20000 N3 5 0.352157 0.872355 0.257874 11.00000 0.03804 0.02466 = 0.02367 -0.00521 -0.00152 0.00443 N4 5 0.092935 0.808191 0.256295 11.00000 0.03361 0.03244 = 0.02880 -0.00503 0.00458 -0.00165 H4 2 0.096765 0.736086 0.296145 11.00000 -1.20000 C1 1 0.966289 0.393784 0.187459 11.00000 0.02126 0.03862 = 0.03076 -0.00178 -0.00401 0.00293 AFIX 43 H1 2 1.013623 0.413465 0.239247 11.00000 -1.20000 AFIX 0 C2 1 1.064873 0.365147 0.101298 11.00000 0.03005 0.05006 = 0.04700 -0.00572 0.00428 0.00583 AFIX 43 H2A 2 1.179457 0.363637 0.094914 11.00000 -1.20000 AFIX 0 C3 1 0.997236 0.338675 0.024319 11.00000 0.05725 0.04324 = 0.03286 -0.00621 0.00590 0.00551 AFIX 43 H3 2 1.064317 0.318943 -0.034949 11.00000 -1.20000 AFIX 0 C4 1 0.829921 0.341576 0.035566 11.00000 0.04605 0.02593 = 0.02752 -0.00298 0.00920 0.00355 C5 1 0.736769 0.370480 0.126428 11.00000 0.04068 0.02481 = 0.03016 -0.00373 -0.00056 -0.00091 C6 1 0.712073 0.327939 -0.021654 11.00000 0.05568 0.03024 = 0.02766 -0.00886 0.00644 0.00400 AFIX 43 H6 2 0.733545 0.308557 -0.087194 11.00000 -1.20000 AFIX 0 C7 1 0.564648 0.347148 0.032763 11.00000 0.05631 0.02837 = 0.03002 -0.00713 -0.00549 -0.01161 AFIX 43 H7 2 0.464997 0.344270 0.010279 11.00000 -1.20000 AFIX 0 C8 1 0.459012 0.953190 0.212457 11.00000 0.04490 0.02831 = 0.04740 -0.01204 0.00497 -0.00823 AFIX 43 H8 2 0.559152 0.947560 0.237104 11.00000 -1.20000 AFIX 0 C9 1 0.424759 1.043795 0.130791 11.00000 0.06983 0.02840 = 0.05236 -0.00027 0.01057 -0.01395 AFIX 43 H9 2 0.503196 1.097837 0.099060 11.00000 -1.20000 AFIX 0 C10 1 0.279471 1.057342 0.094509 11.00000 0.07334 0.02647 = 0.03685 0.00669 0.00215 0.00548 AFIX 43 H10 2 0.255818 1.120801 0.038954 11.00000 -1.20000 AFIX 0 C11 1 0.168172 0.975676 0.141322 11.00000 0.05503 0.03089 = 0.02295 -0.00390 -0.00425 0.00951 C12 1 0.211165 0.881550 0.222366 11.00000 0.04065 0.02173 = 0.02227 -0.00450 0.00237 0.00343 C13 1 0.010967 0.954354 0.129722 11.00000 0.05010 0.06101 = 0.02921 -0.01180 -0.00890 0.01965 AFIX 43 H13 2 -0.054622 1.003286 0.082386 11.00000 -1.20000 AFIX 0 C14 1 -0.029175 0.852329 0.197735 11.00000 0.03600 0.06247 = 0.03286 -0.01726 -0.00091 0.00194 AFIX 43 H14 2 -0.126780 0.816407 0.204244 11.00000 -1.20000 AFIX 0 PART 1 N5 5 0.364055 0.726551 0.542981 10.50000 0.02441 0.02194 = 0.01350 -0.00482 -0.00358 -0.00114 N6 5 0.087686 0.691389 0.550738 10.50000 0.02763 0.03191 = 0.02241 -0.00171 -0.00819 -0.00400 AFIX 43 H6A 2 0.104854 0.616517 0.530521 10.50000 -1.20000 AFIX 0 C15 1 0.459538 0.808675 0.556134 10.50000 0.03355 0.03165 = 0.02085 -0.00404 -0.00500 -0.01159 AFIX 43 H15 2 0.574663 0.788121 0.541229 10.50000 -1.20000 AFIX 0 C16 1 0.394659 0.921286 0.590528 10.50000 0.04025 0.03587 = 0.03550 -0.01298 -0.00834 -0.01101 AFIX 43 H16 2 0.465152 0.975170 0.602481 10.50000 -1.20000 AFIX 0 C17 1 0.230054 0.956493 0.607683 10.50000 0.04152 0.03456 = 0.03206 -0.01063 -0.00447 -0.00735 AFIX 43 H17 2 0.185686 1.035839 0.629560 10.50000 -1.20000 AFIX 0 C18 1 0.128771 0.876553 0.593143 10.50000 0.02725 0.02594 = 0.02379 -0.00506 0.00093 0.00065 C19 1 0.203767 0.760126 0.558787 10.50000 0.02499 0.02424 = 0.01163 -0.00127 -0.00312 0.00016 C20 1 -0.041586 0.871720 0.605131 10.50000 0.02671 0.03585 = 0.03387 -0.00270 0.00053 0.00063 AFIX 43 H20 2 -0.126017 0.935825 0.627002 10.50000 -1.20000 AFIX 0 C21 1 -0.063157 0.759819 0.579990 10.50000 0.02731 0.03897 = 0.03841 -0.00253 -0.00625 -0.00203 AFIX 43 H21 2 -0.165590 0.732774 0.582138 10.50000 -1.20000 AFIX 0 PART 2 N7 5 0.274804 0.691251 0.531265 10.50000 0.03346 0.02878 = 0.01499 -0.00203 0.00083 -0.00116 N8 5 0.470711 0.798652 0.571900 10.50000 0.03505 0.03844 = 0.03554 -0.01160 0.00184 -0.00488 AFIX 43 H8A 2 0.560125 0.744236 0.559725 10.50000 -1.20000 AFIX 0 C22 1 0.114511 0.690797 0.529012 10.50000 0.03460 0.03601 = 0.01972 -0.00266 -0.00231 -0.00275 AFIX 43 H22 2 0.083377 0.622403 0.505274 10.50000 -1.20000 AFIX 0 C23 1 -0.004541 0.785985 0.559925 10.50000 0.03418 0.04056 = 0.03296 -0.00726 -0.00814 0.00124 AFIX 43 H23 2 -0.116273 0.782241 0.558944 10.50000 -1.20000 AFIX 0 C24 1 0.039835 0.886388 0.592188 10.50000 0.03614 0.03848 = 0.03093 -0.00777 -0.00300 -0.00011 AFIX 43 H24 2 -0.041267 0.952526 0.614237 10.50000 -1.20000 AFIX 0 C25 1 0.200049 0.891096 0.592559 10.50000 0.03719 0.02902 = 0.02428 -0.00418 -0.00154 -0.00085 C26 1 0.317765 0.787842 0.560868 10.50000 0.03545 0.02731 = 0.02026 -0.00101 0.00222 -0.00336 C27 1 0.298196 0.969730 0.620036 10.50000 0.03934 0.04138 = 0.05089 -0.02164 0.00262 -0.00506 AFIX 43 H27 2 0.259508 1.048541 0.643962 10.50000 -1.20000 AFIX 0 C28 1 0.457119 0.913762 0.606512 10.50000 0.03797 0.05082 = 0.07422 -0.03319 0.00102 -0.00555 AFIX 43 H28 2 0.546324 0.948806 0.619075 10.50000 -1.20000 AFIX 0 HKLF 4 REM ow5aw_0m_a.res in P-1 REM wR2 = 0.064389, GooF = S = 1.07794, Restrained GooF = 1.06801 for all data REM R1 = 0.033116 for 5114 Fo > 4sig(Fo) and 0.045371 for all 5964 data REM 394 parameters refined using 174 restraints END WGHT 0.0113 3.0433 REM Highest difference peak 2.124, deepest hole -1.364, 1-sigma level 0.118 Q1 1 0.2232 0.5242 0.3411 11.00000 0.05 2.12 Q2 1 0.6804 0.3906 0.1850 11.00000 0.05 1.41 Q3 1 0.8520 0.3722 0.1363 11.00000 0.05 1.01 Q4 1 0.8074 0.5986 0.3723 11.00000 0.05 0.84 Q5 1 0.6090 0.4127 0.2671 11.00000 0.05 0.68 Q6 1 0.5465 0.6788 0.1541 11.00000 0.05 0.64 Q7 1 0.4455 0.5780 0.3451 11.00000 0.05 0.56 Q8 1 0.3931 0.4224 0.2613 11.00000 0.05 0.54 Q9 1 0.9169 0.3749 0.0547 11.00000 0.05 0.49 Q10 1 0.4200 0.5407 0.2764 11.00000 0.05 0.47 Q11 1 0.2935 0.4111 0.3154 11.00000 0.05 0.47 Q12 1 0.1281 0.4953 0.3968 11.00000 0.05 0.47 Q13 1 0.8100 0.2895 0.0027 11.00000 0.05 0.43 Q14 1 0.8966 0.3034 0.0461 11.00000 0.05 0.43 Q15 1 0.5873 0.6037 0.2358 11.00000 0.05 0.42 Q16 1 0.3942 0.4523 0.2415 11.00000 0.05 0.42 Q17 1 0.7167 0.4425 0.2969 11.00000 0.05 0.41 Q18 1 0.0024 0.5536 0.4976 11.00000 0.05 0.41 Q19 1 0.7015 0.5770 0.3456 11.00000 0.05 0.40 Q20 1 0.6648 0.6640 0.3176 11.00000 0.05 0.39 ; _shelx_res_checksum 42010 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Eu1 Eu 0.54434(2) 0.58288(2) 0.34687(2) 0.02347(6) Uani 1 1 d . . . . . Cl1 Cl 0.79770(16) 0.65898(15) 0.40188(8) 0.0608(4) Uani 1 1 d . . . . . Cl2 Cl 0.29349(13) 0.48825(11) 0.30261(8) 0.0434(3) Uani 1 1 d . . . . . Cl3 Cl 0.63905(11) 0.68855(9) 0.15667(6) 0.02897(19) Uani 1 1 d . . . . . O1 O 0.7046(4) 0.4160(3) 0.28308(17) 0.0362(7) Uani 1 1 d . . . . . O2 O 0.3833(3) 0.7836(2) 0.33682(18) 0.0337(6) Uani 1 1 d . . . . . O3 O 0.4096(3) 0.6013(2) 0.51442(18) 0.0363(7) Uani 1 1 d . . . . . N1 N 0.8042(4) 0.3940(3) 0.1986(2) 0.0343(8) Uani 1 1 d . . . . . N2 N 0.5756(4) 0.3717(3) 0.1259(2) 0.0283(7) Uani 1 1 d D . . . . H2 H 0.497(4) 0.389(4) 0.175(2) 0.034 Uiso 1 1 d D U . . . N3 N 0.3522(4) 0.8724(3) 0.2579(2) 0.0301(7) Uani 1 1 d . . . . . N4 N 0.0929(4) 0.8082(3) 0.2563(2) 0.0331(7) Uani 1 1 d D . . . . H4 H 0.097(5) 0.736(3) 0.296(3) 0.040 Uiso 1 1 d D U . . . C1 C 0.9663(4) 0.3938(4) 0.1875(3) 0.0316(8) Uani 1 1 d . . . . . H1 H 1.013623 0.413465 0.239247 0.038 Uiso 1 1 calc R U . . . C2 C 1.0649(5) 0.3651(4) 0.1013(3) 0.0453(11) Uani 1 1 d . . . . . H2A H 1.179457 0.363637 0.094914 0.054 Uiso 1 1 calc R U . . . C3 C 0.9972(6) 0.3387(4) 0.0243(3) 0.0475(12) Uani 1 1 d . . . . . H3 H 1.064317 0.318943 -0.034949 0.057 Uiso 1 1 calc R U . . . C4 C 0.8299(5) 0.3416(4) 0.0356(3) 0.0362(10) Uani 1 1 d . . . . . C5 C 0.7368(5) 0.3705(4) 0.1264(3) 0.0330(9) Uani 1 1 d . . . . . C6 C 0.7121(6) 0.3279(4) -0.0217(3) 0.0401(10) Uani 1 1 d . . . . . H6 H 0.733545 0.308557 -0.087194 0.048 Uiso 1 1 calc R U . . . C7 C 0.5646(6) 0.3471(4) 0.0328(3) 0.0373(10) Uani 1 1 d . . . . . H7 H 0.464997 0.344270 0.010279 0.045 Uiso 1 1 calc R U . . . C8 C 0.4590(6) 0.9532(4) 0.2125(3) 0.0405(10) Uani 1 1 d . . . . . H8 H 0.559152 0.947560 0.237104 0.049 Uiso 1 1 calc R U . . . C9 C 0.4248(7) 1.0438(4) 0.1308(4) 0.0525(13) Uani 1 1 d . . . . . H9 H 0.503196 1.097837 0.099060 0.063 Uiso 1 1 calc R U . . . C10 C 0.2795(7) 1.0573(4) 0.0945(3) 0.0499(13) Uani 1 1 d . . . . . H10 H 0.255818 1.120801 0.038954 0.060 Uiso 1 1 calc R U . . . C11 C 0.1682(6) 0.9757(4) 0.1413(3) 0.0385(10) Uani 1 1 d . . . . . C12 C 0.2112(5) 0.8816(3) 0.2224(3) 0.0299(8) Uani 1 1 d . . . . . C13 C 0.0110(6) 0.9544(5) 0.1297(3) 0.0492(12) Uani 1 1 d . . . . . H13 H -0.054622 1.003286 0.082386 0.059 Uiso 1 1 calc R U . . . C14 C -0.0292(6) 0.8523(5) 0.1977(3) 0.0441(11) Uani 1 1 d . . . . . H14 H -0.126780 0.816407 0.204244 0.053 Uiso 1 1 calc R U . . . N5 N 0.3641(7) 0.7266(6) 0.5430(4) 0.0199(10) Uani 0.5 1 d D . P A 1 N6 N 0.0877(10) 0.6914(12) 0.5507(10) 0.027(2) Uani 0.5 1 d D . P A 1 H6A H 0.104854 0.616517 0.530521 0.033 Uiso 0.5 1 calc R U P A 1 C15 C 0.4595(18) 0.8087(18) 0.556(2) 0.028(2) Uani 0.5 1 d D . P A 1 H15 H 0.574663 0.788121 0.541229 0.033 Uiso 0.5 1 calc R U P A 1 C16 C 0.3947(12) 0.9213(9) 0.5905(8) 0.0352(18) Uani 0.5 1 d D . P A 1 H16 H 0.465152 0.975170 0.602481 0.042 Uiso 0.5 1 calc R U P A 1 C17 C 0.2301(11) 0.9565(10) 0.6077(7) 0.0352(18) Uani 0.5 1 d D . P A 1 H17 H 0.185686 1.035839 0.629560 0.042 Uiso 0.5 1 calc R U P A 1 C18 C 0.1288(12) 0.8766(7) 0.5931(6) 0.0266(15) Uani 0.5 1 d D . P A 1 C19 C 0.2038(8) 0.7601(7) 0.5588(4) 0.0209(11) Uani 0.5 1 d D . P A 1 C20 C -0.0416(11) 0.8717(8) 0.6051(6) 0.0338(17) Uani 0.5 1 d D . P A 1 H20 H -0.126017 0.935825 0.627002 0.041 Uiso 0.5 1 calc R U P A 1 C21 C -0.0632(11) 0.7598(9) 0.5800(8) 0.036(2) Uani 0.5 1 d D . P A 1 H21 H -0.165590 0.732774 0.582138 0.043 Uiso 0.5 1 calc R U P A 1 N7 N 0.2748(8) 0.6913(6) 0.5313(4) 0.0269(11) Uani 0.5 1 d D . P A 2 N8 N 0.4707(15) 0.7987(16) 0.5719(19) 0.037(4) Uani 0.5 1 d D . P A 2 H8A H 0.560125 0.744236 0.559725 0.044 Uiso 0.5 1 calc R U P A 2 C22 C 0.1145(13) 0.6908(15) 0.5290(13) 0.031(2) Uani 0.5 1 d D . P A 2 H22 H 0.083377 0.622403 0.505274 0.037 Uiso 0.5 1 calc R U P A 2 C23 C -0.0045(12) 0.7860(9) 0.5599(8) 0.0362(19) Uani 0.5 1 d D . P A 2 H23 H -0.116273 0.782241 0.558944 0.043 Uiso 0.5 1 calc R U P A 2 C24 C 0.0398(14) 0.8864(8) 0.5922(7) 0.0358(18) Uani 0.5 1 d D . P A 2 H24 H -0.041267 0.952526 0.614237 0.043 Uiso 0.5 1 calc R U P A 2 C25 C 0.2000(12) 0.8911(9) 0.5926(6) 0.0310(16) Uani 0.5 1 d D . P A 2 C26 C 0.3178(10) 0.7878(8) 0.5609(5) 0.0290(13) Uani 0.5 1 d D . P A 2 C27 C 0.2982(13) 0.9697(10) 0.6200(8) 0.043(2) Uani 0.5 1 d D . P A 2 H27 H 0.259508 1.048541 0.643962 0.052 Uiso 0.5 1 calc R U P A 2 C28 C 0.4571(13) 0.9138(11) 0.6065(11) 0.052(3) Uani 0.5 1 d D . P A 2 H28 H 0.546324 0.948806 0.619075 0.063 Uiso 0.5 1 calc R U P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.02766(10) 0.02635(10) 0.01270(8) -0.00290(6) -0.00088(6) 0.00376(7) Cl1 0.0573(8) 0.0997(11) 0.0349(6) -0.0033(6) -0.0168(5) -0.0355(7) Cl2 0.0389(6) 0.0506(7) 0.0415(6) -0.0002(5) -0.0089(5) -0.0138(5) Cl3 0.0356(5) 0.0319(5) 0.0167(4) -0.0031(3) 0.0000(3) -0.0022(4) O1 0.0485(17) 0.0371(16) 0.0148(11) -0.0053(11) 0.0030(11) 0.0094(13) O2 0.0447(17) 0.0305(14) 0.0185(12) -0.0009(10) -0.0028(11) 0.0093(12) O3 0.0468(17) 0.0302(15) 0.0182(12) -0.0013(10) 0.0068(11) 0.0172(12) N1 0.040(2) 0.0295(18) 0.0284(16) -0.0030(13) -0.0023(14) 0.0032(15) N2 0.0298(17) 0.0293(17) 0.0251(15) -0.0040(13) 0.0013(13) -0.0082(14) N3 0.0380(19) 0.0247(16) 0.0237(15) -0.0052(12) -0.0015(14) 0.0044(14) N4 0.0336(18) 0.0324(19) 0.0288(16) -0.0050(14) 0.0046(14) -0.0017(15) C1 0.0213(18) 0.039(2) 0.0308(19) -0.0018(16) -0.0040(15) 0.0029(16) C2 0.030(2) 0.050(3) 0.047(3) -0.006(2) 0.0043(19) 0.006(2) C3 0.057(3) 0.043(3) 0.033(2) -0.0062(19) 0.006(2) 0.006(2) C4 0.046(2) 0.026(2) 0.0275(19) -0.0030(15) 0.0092(18) 0.0035(18) C5 0.041(2) 0.025(2) 0.0302(19) -0.0037(15) -0.0006(17) -0.0009(17) C6 0.056(3) 0.030(2) 0.0277(19) -0.0089(16) 0.0064(19) 0.0040(19) C7 0.056(3) 0.028(2) 0.030(2) -0.0071(16) -0.0055(19) -0.0116(19) C8 0.045(3) 0.028(2) 0.047(2) -0.0120(19) 0.005(2) -0.0082(19) C9 0.070(4) 0.028(2) 0.052(3) 0.000(2) 0.011(3) -0.014(2) C10 0.073(4) 0.026(2) 0.037(2) 0.0067(18) 0.002(2) 0.005(2) C11 0.055(3) 0.031(2) 0.0229(18) -0.0039(16) -0.0043(18) 0.0095(19) C12 0.041(2) 0.0217(19) 0.0223(17) -0.0045(14) 0.0024(16) 0.0034(16) C13 0.050(3) 0.061(3) 0.029(2) -0.012(2) -0.009(2) 0.020(2) C14 0.036(2) 0.062(3) 0.033(2) -0.017(2) -0.0009(18) 0.002(2) N5 0.024(2) 0.022(3) 0.013(2) -0.005(2) -0.0036(18) -0.0011(19) N6 0.028(3) 0.032(3) 0.022(6) -0.002(3) -0.008(3) -0.004(2) C15 0.034(3) 0.032(3) 0.021(6) -0.004(4) -0.005(3) -0.012(3) C16 0.040(3) 0.036(3) 0.035(4) -0.013(3) -0.008(3) -0.011(3) C17 0.042(3) 0.035(3) 0.032(4) -0.011(3) -0.004(3) -0.007(2) C18 0.027(3) 0.026(3) 0.024(4) -0.005(2) 0.001(3) 0.001(2) C19 0.0250(19) 0.024(2) 0.012(3) -0.001(2) -0.0031(19) 0.0002(18) C20 0.027(3) 0.036(3) 0.034(4) -0.003(3) 0.001(3) 0.001(2) C21 0.027(2) 0.039(4) 0.038(5) -0.003(3) -0.006(3) -0.002(2) N7 0.033(3) 0.029(3) 0.015(3) -0.002(2) 0.001(2) -0.001(2) N8 0.035(3) 0.038(4) 0.036(10) -0.012(6) 0.002(3) -0.005(2) C22 0.035(3) 0.036(4) 0.020(6) -0.003(4) -0.002(3) -0.003(3) C23 0.034(3) 0.041(4) 0.033(5) -0.007(3) -0.008(4) 0.001(3) C24 0.036(3) 0.038(4) 0.031(4) -0.008(3) -0.003(4) 0.000(3) C25 0.037(3) 0.029(3) 0.024(4) -0.004(3) -0.002(3) -0.001(2) C26 0.035(3) 0.027(3) 0.020(3) -0.001(2) 0.002(2) -0.003(2) C27 0.039(4) 0.041(4) 0.051(5) -0.022(4) 0.003(4) -0.005(3) C28 0.038(4) 0.051(5) 0.074(8) -0.033(5) 0.001(4) -0.006(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 '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' 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 Cl1 Eu1 Eu1 83.60(3) . 2_666 ? Cl1 Eu1 Cl2 175.23(4) . . ? Cl1 Eu1 Cl3 89.62(3) . . ? Cl2 Eu1 Eu1 92.49(2) . 2_666 ? Cl2 Eu1 Cl3 94.17(3) . . ? Cl3 Eu1 Eu1 172.83(2) . 2_666 ? O1 Eu1 Eu1 100.74(6) . 2_666 ? O1 Eu1 Cl1 92.62(8) . . ? O1 Eu1 Cl2 85.40(8) . . ? O1 Eu1 Cl3 77.16(7) . . ? O1 Eu1 O2 154.40(9) . . ? O1 Eu1 O3 71.20(8) . 2_666 ? O1 Eu1 O3 131.33(9) . . ? O2 Eu1 Eu1 104.33(6) . 2_666 ? O2 Eu1 Cl1 95.20(8) . . ? O2 Eu1 Cl2 88.41(8) . . ? O2 Eu1 Cl3 78.56(6) . . ? O2 Eu1 O3 73.69(8) . . ? O2 Eu1 O3 133.90(8) . 2_666 ? O3 Eu1 Eu1 29.59(5) 2_666 2_666 ? O3 Eu1 Eu1 30.66(6) . 2_666 ? O3 Eu1 Cl1 85.47(8) . . ? O3 Eu1 Cl1 83.50(8) 2_666 . ? O3 Eu1 Cl2 92.57(8) . . ? O3 Eu1 Cl2 91.74(8) 2_666 . ? O3 Eu1 Cl3 147.20(6) 2_666 . ? O3 Eu1 Cl3 151.22(6) . . ? O3 Eu1 O3 60.25(10) . 2_666 ? N1 O1 Eu1 138.7(2) . . ? N3 O2 Eu1 130.5(2) . . ? Eu1 O3 Eu1 119.75(10) . 2_666 ? N5 O3 Eu1 115.9(3) . 2_666 ? N5 O3 Eu1 119.3(3) . . ? N7 O3 Eu1 121.1(3) . . ? C1 N1 O1 122.5(3) . . ? C5 N1 O1 117.2(3) . . ? C5 N1 C1 120.2(3) . . ? C5 N2 H2 126(3) . . ? C5 N2 C7 105.2(3) . . ? C7 N2 H2 129(3) . . ? O2 N3 C8 121.9(4) . . ? O2 N3 C12 119.2(3) . . ? C12 N3 C8 118.9(3) . . ? C12 N4 H4 129(3) . . ? C12 N4 C14 107.1(4) . . ? C14 N4 H4 123(3) . . ? N1 C1 H1 119.7 . . ? N1 C1 C2 120.7(4) . . ? C2 C1 H1 119.7 . . ? C1 C2 H2A 119.8 . . ? C1 C2 C3 120.3(4) . . ? C3 C2 H2A 119.8 . . ? C2 C3 H3 120.7 . . ? C4 C3 C2 118.6(4) . . ? C4 C3 H3 120.7 . . ? C3 C4 C5 117.9(4) . . ? C3 C4 C6 138.0(4) . . ? C6 C4 C5 104.1(4) . . ? N1 C5 N2 126.7(4) . . ? N1 C5 C4 122.2(4) . . ? N2 C5 C4 111.1(4) . . ? C4 C6 H6 126.0 . . ? C7 C6 C4 108.0(4) . . ? C7 C6 H6 126.0 . . ? N2 C7 H7 124.2 . . ? C6 C7 N2 111.6(4) . . ? C6 C7 H7 124.2 . . ? N3 C8 H8 119.5 . . ? N3 C8 C9 121.0(4) . . ? C9 C8 H8 119.5 . . ? C8 C9 H9 119.4 . . ? C10 C9 C8 121.3(4) . . ? C10 C9 H9 119.4 . . ? C9 C10 H10 120.9 . . ? C9 C10 C11 118.1(4) . . ? C11 C10 H10 120.9 . . ? C10 C11 C12 118.5(4) . . ? C10 C11 C13 137.3(4) . . ? C12 C11 C13 104.2(4) . . ? N3 C12 N4 127.1(3) . . ? N3 C12 C11 122.2(4) . . ? N4 C12 C11 110.7(4) . . ? C11 C13 H13 125.9 . . ? C14 C13 C11 108.2(4) . . ? C14 C13 H13 125.9 . . ? N4 C14 H14 125.1 . . ? C13 C14 N4 109.8(4) . . ? C13 C14 H14 125.1 . . ? C15 N5 O3 129.4(8) . . ? C19 N5 O3 112.3(6) . . ? C19 N5 C15 118.3(9) . . ? C19 N6 H6A 126.1 . . ? C19 N6 C21 107.9(8) . . ? C21 N6 H6A 126.1 . . ? N5 C15 H15 119.2 . . ? N5 C15 C16 121.6(13) . . ? C16 C15 H15 119.2 . . ? C15 C16 H16 119.7 . . ? C17 C16 C15 120.5(9) . . ? C17 C16 H16 119.7 . . ? C16 C17 H17 120.3 . . ? C16 C17 C18 119.5(9) . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 117.2(8) . . ? C17 C18 C20 138.2(8) . . ? C20 C18 C19 104.6(7) . . ? N5 C19 N6 127.5(8) . . ? N5 C19 C18 122.7(7) . . ? N6 C19 C18 109.7(7) . . ? C18 C20 H20 125.8 . . ? C21 C20 C18 108.5(7) . . ? C21 C20 H20 125.8 . . ? N6 C21 H21 125.3 . . ? C20 C21 N6 109.4(9) . . ? C20 C21 H21 125.3 . . ? C22 N7 O3 131.7(7) . . ? C26 N7 O3 109.4(7) . . ? C26 N7 C22 118.7(9) . . ? C26 N8 H8A 127.3 . . ? C26 N8 C28 105.3(11) . . ? C28 N8 H8A 127.3 . . ? N7 C22 H22 118.9 . . ? N7 C22 C23 122.2(11) . . ? C23 C22 H22 118.9 . . ? C22 C23 H23 120.4 . . ? C24 C23 C22 119.2(10) . . ? C24 C23 H23 120.4 . . ? C23 C24 H24 120.1 . . ? C25 C24 C23 119.8(9) . . ? C25 C24 H24 120.1 . . ? C24 C25 C26 118.2(9) . . ? C24 C25 C27 139.1(8) . . ? C27 C25 C26 102.7(7) . . ? N7 C26 N8 125.6(10) . . ? N7 C26 C25 121.9(8) . . ? N8 C26 C25 112.4(9) . . ? C25 C27 H27 125.6 . . ? C28 C27 C25 108.8(9) . . ? C28 C27 H27 125.6 . . ? N8 C28 H28 124.7 . . ? C27 C28 N8 110.7(10) . . ? C27 C28 H28 124.7 . . ? 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 Eu1 Eu1 4.2727(4) 2_666 ? Eu1 Cl1 2.6810(12) . ? Eu1 Cl2 2.6989(11) . ? Eu1 Cl3 2.7080(8) . ? Eu1 O1 2.268(2) . ? Eu1 O2 2.327(2) . ? Eu1 O3 2.430(2) . ? Eu1 O3 2.509(2) 2_666 ? O1 N1 1.352(4) . ? O2 N3 1.338(4) . ? O3 N5 1.441(7) . ? O3 N7 1.372(7) . ? N1 C1 1.345(5) . ? N1 C5 1.313(5) . ? N2 H2 0.885(18) . ? N2 C5 1.354(5) . ? N2 C7 1.385(5) . ? N3 C8 1.352(5) . ? N3 C12 1.341(5) . ? N4 H4 0.860(19) . ? N4 C12 1.343(5) . ? N4 C14 1.381(5) . ? C1 H1 0.9500 . ? C1 C2 1.385(5) . ? C2 H2A 0.9500 . ? C2 C3 1.386(7) . ? C3 H3 0.9500 . ? C3 C4 1.384(6) . ? C4 C5 1.421(5) . ? C4 C6 1.413(6) . ? C6 H6 0.9500 . ? C6 C7 1.340(6) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C8 C9 1.381(6) . ? C9 H9 0.9500 . ? C9 C10 1.374(7) . ? C10 H10 0.9500 . ? C10 C11 1.389(6) . ? C11 C12 1.412(5) . ? C11 C13 1.421(7) . ? C13 H13 0.9500 . ? C13 C14 1.353(7) . ? C14 H14 0.9500 . ? N5 C15 1.346(11) . ? N5 C19 1.324(8) . ? N6 H6A 0.8800 . ? N6 C19 1.352(9) . ? N6 C21 1.386(11) . ? C15 H15 0.9500 . ? C15 C16 1.371(13) . ? C16 H16 0.9500 . ? C16 C17 1.361(10) . ? C17 H17 0.9500 . ? C17 C18 1.371(10) . ? C18 C19 1.424(9) . ? C18 C20 1.423(10) . ? C20 H20 0.9500 . ? C20 C21 1.360(11) . ? C21 H21 0.9500 . ? N7 C22 1.355(11) . ? N7 C26 1.309(9) . ? N8 H8A 0.8800 . ? N8 C26 1.348(11) . ? N8 C28 1.386(13) . ? C22 H22 0.9500 . ? C22 C23 1.374(11) . ? C23 H23 0.9500 . ? C23 C24 1.370(10) . ? C24 H24 0.9500 . ? C24 C25 1.358(10) . ? C25 C26 1.432(10) . ? C25 C27 1.418(12) . ? C27 H27 0.9500 . ? C27 C28 1.363(12) . ? C28 H28 0.9500 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H2 Cl2 0.885(18) 2.50(2) 3.364(3) 166(4) . yes N4 H4 Cl2 0.860(19) 2.87(3) 3.541(4) 136(4) . yes N6 H6A Cl1 0.88 2.94 3.673(13) 141.9 2_666 yes N8 H8A Cl1 0.88 2.87 3.609(18) 142.8 . yes N8 H8A Cl2 0.88 3.05 3.67(2) 128.9 2_666 yes 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 Eu1 O1 N1 C1 94.3(4) . . . . ? Eu1 O1 N1 C5 -86.7(5) . . . . ? Eu1 O2 N3 C8 -79.6(4) . . . . ? Eu1 O2 N3 C12 100.2(3) . . . . ? Eu1 O3 N5 C15 -68.8(18) . . . . ? Eu1 O3 N5 C15 85.9(18) 2_666 . . . ? Eu1 O3 N5 C19 112.2(5) . . . . ? Eu1 O3 N5 C19 -93.2(5) 2_666 . . . ? Eu1 O3 N7 C22 -78.2(12) 2_666 . . . ? Eu1 O3 N7 C22 83.0(13) . . . . ? Eu1 O3 N7 C26 -102.2(5) . . . . ? Eu1 O3 N7 C26 96.6(5) 2_666 . . . ? O1 N1 C1 C2 177.1(4) . . . . ? O1 N1 C5 N2 3.3(6) . . . . ? O1 N1 C5 C4 -177.7(3) . . . . ? O2 N3 C8 C9 179.7(4) . . . . ? O2 N3 C12 N4 -1.4(5) . . . . ? O2 N3 C12 C11 177.9(3) . . . . ? O3 N5 C15 C16 -175.3(14) . . . . ? O3 N5 C19 N6 -0.1(11) . . . . ? O3 N5 C19 C18 176.4(6) . . . . ? O3 N7 C22 C23 172.1(9) . . . . ? O3 N7 C26 N8 0.9(16) . . . . ? O3 N7 C26 C25 -174.3(6) . . . . ? N1 C1 C2 C3 1.3(7) . . . . ? N3 C8 C9 C10 1.8(7) . . . . ? C1 N1 C5 N2 -177.6(4) . . . . ? C1 N1 C5 C4 1.3(6) . . . . ? C1 C2 C3 C4 0.0(7) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C2 C3 C4 C6 176.2(5) . . . . ? C3 C4 C5 N1 0.0(6) . . . . ? C3 C4 C5 N2 179.1(4) . . . . ? C3 C4 C6 C7 -177.3(5) . . . . ? C4 C6 C7 N2 -0.9(5) . . . . ? C5 N1 C1 C2 -1.9(6) . . . . ? C5 N2 C7 C6 1.6(5) . . . . ? C5 C4 C6 C7 -0.2(5) . . . . ? C6 C4 C5 N1 -177.8(4) . . . . ? C6 C4 C5 N2 1.2(4) . . . . ? C7 N2 C5 N1 177.3(4) . . . . ? C7 N2 C5 C4 -1.7(4) . . . . ? C8 N3 C12 N4 178.5(4) . . . . ? C8 N3 C12 C11 -2.2(5) . . . . ? C8 C9 C10 C11 -1.0(7) . . . . ? C9 C10 C11 C12 -1.2(6) . . . . ? C9 C10 C11 C13 -179.1(5) . . . . ? C10 C11 C12 N3 2.9(6) . . . . ? C10 C11 C12 N4 -177.7(3) . . . . ? C10 C11 C13 C14 176.3(5) . . . . ? C11 C13 C14 N4 2.2(5) . . . . ? C12 N3 C8 C9 -0.1(6) . . . . ? C12 N4 C14 C13 -1.6(5) . . . . ? C12 C11 C13 C14 -1.8(5) . . . . ? C13 C11 C12 N3 -178.5(3) . . . . ? C13 C11 C12 N4 0.9(4) . . . . ? C14 N4 C12 N3 179.7(4) . . . . ? C14 N4 C12 C11 0.4(4) . . . . ? N5 C15 C16 C17 -3(3) . . . . ? C15 N5 C19 N6 -179.3(18) . . . . ? C15 N5 C19 C18 -2.8(18) . . . . ? C15 C16 C17 C18 2(2) . . . . ? C16 C17 C18 C19 -1.0(12) . . . . ? C16 C17 C18 C20 176.7(10) . . . . ? C17 C18 C19 N5 1.5(11) . . . . ? C17 C18 C19 N6 178.5(9) . . . . ? C17 C18 C20 C21 -177.5(11) . . . . ? C18 C20 C21 N6 -0.7(12) . . . . ? C19 N5 C15 C16 4(3) . . . . ? C19 N6 C21 C20 0.7(13) . . . . ? C19 C18 C20 C21 0.3(9) . . . . ? C20 C18 C19 N5 -176.9(6) . . . . ? C20 C18 C19 N6 0.1(10) . . . . ? C21 N6 C19 N5 176.4(8) . . . . ? C21 N6 C19 C18 -0.5(13) . . . . ? N7 C22 C23 C24 1(2) . . . . ? C22 N7 C26 N8 176.4(17) . . . . ? C22 N7 C26 C25 1.2(14) . . . . ? C22 C23 C24 C25 0.5(16) . . . . ? C23 C24 C25 C26 -1.4(13) . . . . ? C23 C24 C25 C27 -178.1(11) . . . . ? C24 C25 C26 N7 0.6(12) . . . . ? C24 C25 C26 N8 -175.2(14) . . . . ? C24 C25 C27 C28 175.9(12) . . . . ? C25 C27 C28 N8 -0.8(17) . . . . ? C26 N7 C22 C23 -2(2) . . . . ? C26 N8 C28 C27 2(2) . . . . ? C26 C25 C27 C28 -1.0(11) . . . . ? C27 C25 C26 N7 178.3(8) . . . . ? C27 C25 C26 N8 2.6(15) . . . . ? C28 N8 C26 N7 -178.6(11) . . . . ? C28 N8 C26 C25 -3(2) . . . . ?