#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:05:58 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288809 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247626.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_7247626 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 'C21 H18 Eu N9 O12' _chemical_formula_sum 'C21 H18 Eu N9 O12' _chemical_formula_weight 740.40 _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 78.6540(10) _cell_angle_beta 77.1540(10) _cell_angle_gamma 70.8060(10) _cell_formula_units_Z 2 _cell_length_a 8.5699(4) _cell_length_b 11.7452(6) _cell_length_c 14.2218(7) _cell_measurement_reflns_used 9950 _cell_measurement_temperature 150.0 _cell_measurement_theta_max 30.511 _cell_measurement_theta_min 2.703 _cell_volume 1306.15(11) _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 150.0 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _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 0.0217 _diffrn_reflns_av_unetI/netI 0.0168 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 37986 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.543 _diffrn_reflns_theta_min 3.164 _diffrn_source_current 20.0 _diffrn_source_power 1.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.484 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6391 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0553 before and 0.0358 after correction. The Ratio of minimum to maximum transmission is 0.8566. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.883 _exptl_crystal_description Block _exptl_crystal_F_000 732 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.487 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 397 _refine_ls_number_reflns 7957 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.169 _refine_ls_R_factor_all 0.0169 _refine_ls_R_factor_gt 0.0159 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0097P)^2^+0.8269P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0381 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7700 _reflns_number_total 7957 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00985h2.cif _cod_data_source_block 2 _cod_depositor_comments 'Adding full bibliography for 7247622--7247628.cif.' _cod_database_code 7247626 _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 0.663 _shelx_estimated_absorpt_t_min 0.523 _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 = N6-H6 0.88 with sigma of 0.02 3.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2A), C3(H3), C6(H6A), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21) ; _shelx_res_file ; TITL ow5bl_et2o_0m_a.res in P-1 ow5bl_et2o_0m.res created by SHELXL-2018/3 at 15:02:07 on 02-Aug-2023 REM Old TITL OW5BL_Et2O_0m in P-1 REM SHELXT solution in P-1 REM R1 0.059, Rweak 0.012, Alpha 0.041, Orientation as input REM Formula found by SHELXT: C29 N4 O9 Eu CELL 0.71073 8.5699 11.7452 14.2218 78.654 77.154 70.806 ZERR 2 0.0004 0.0006 0.0007 0.001 0.001 0.001 LATT 1 SFAC C H Eu N O UNIT 42 36 2 18 24 DFIX 0.88 N4 H4 N2 H2 N6 H6 L.S. 4 PLAN 20 SIZE 0.18 0.23 0.3 TEMP -123.15 CONF HTAB N2 O2 HTAB N4 O3 HTAB N6 O1 CONN 12 1.5 $Eu BOND $H list 4 MORE -1 fmap 2 acta OMIT 0 -3 1 OMIT 1 1 0 OMIT 1 1 1 OMIT 0 1 1 OMIT 1 0 0 OMIT 0 0 2 OMIT 0 -1 1 OMIT 0 3 2 REM REM REM WGHT 0.009700 0.826900 FVAR 0.66472 EU1 3 0.522530 0.301796 0.287288 11.00000 0.01600 0.01242 = 0.01326 -0.00230 -0.00176 -0.00437 O1 5 0.295072 0.267623 0.400780 11.00000 0.02357 0.02123 = 0.01341 -0.00463 0.00241 -0.01004 O2 5 0.379192 0.499223 0.323706 11.00000 0.02651 0.01198 = 0.01690 -0.00005 -0.00135 -0.00605 O3 5 0.312657 0.361226 0.189663 11.00000 0.02322 0.01827 = 0.02043 -0.00388 -0.00750 -0.00869 O4 5 0.600012 0.309750 0.446504 11.00000 0.02846 0.02204 = 0.01978 -0.00458 -0.00558 -0.00421 O5 5 0.696641 0.137414 0.391134 11.00000 0.03205 0.01769 = 0.02398 -0.00168 -0.00644 -0.00387 O6 5 0.798151 0.166131 0.508868 11.00000 0.04439 0.05544 = 0.03187 -0.00686 -0.02317 0.00626 O7 5 0.790405 0.347744 0.253392 11.00000 0.02470 0.02296 = 0.01819 0.00147 -0.00629 -0.01092 O8 5 0.631138 0.437590 0.146098 11.00000 0.02000 0.02251 = 0.02057 0.00088 -0.00412 -0.00506 O9 5 0.884973 0.450126 0.121112 11.00000 0.02389 0.03504 = 0.03261 0.00565 0.00208 -0.01370 O10 5 0.702312 0.177480 0.161315 11.00000 0.02860 0.02196 = 0.02165 -0.00700 0.00117 -0.01114 O11 5 0.520997 0.097380 0.255805 11.00000 0.02276 0.02156 = 0.02956 -0.00826 0.00137 -0.00813 O12 5 0.706445 -0.004111 0.146962 11.00000 0.04584 0.02193 = 0.03017 -0.01441 -0.00028 -0.00701 N1 4 0.236029 0.255411 0.496451 11.00000 0.01707 0.01637 = 0.01466 -0.00288 -0.00054 -0.00621 N2 4 0.197608 0.464773 0.508535 11.00000 0.02104 0.01533 = 0.01810 -0.00345 -0.00099 -0.00711 H2 2 0.243697 0.488392 0.451947 11.00000 -1.20000 N3 4 0.397140 0.608639 0.282800 11.00000 0.01793 0.01283 = 0.01584 -0.00179 -0.00132 -0.00383 N4 4 0.268358 0.613337 0.147789 11.00000 0.02508 0.01711 = 0.01955 -0.00363 -0.00769 -0.00324 H4 2 0.266103 0.540893 0.157720 11.00000 -1.20000 N5 4 0.265216 0.300420 0.135826 11.00000 0.01734 0.01806 = 0.01953 -0.00432 -0.00458 -0.00494 N6 4 0.157102 0.181204 0.276729 11.00000 0.01973 0.02318 = 0.01928 -0.00345 -0.00247 -0.00887 H6 2 0.184119 0.207349 0.322102 11.00000 -1.20000 N7 4 0.700685 0.202886 0.451301 11.00000 0.02516 0.02735 = 0.01665 -0.00040 -0.00407 -0.00406 N8 4 0.772742 0.413211 0.171737 11.00000 0.02108 0.01564 = 0.01931 -0.00306 -0.00077 -0.00525 N9 4 0.644531 0.087431 0.186818 11.00000 0.02435 0.01796 = 0.01900 -0.00529 -0.00645 -0.00478 C1 1 0.219254 0.147955 0.544606 11.00000 0.02461 0.01536 = 0.02087 -0.00263 -0.00125 -0.00729 AFIX 43 H1 2 0.256119 0.078613 0.511365 11.00000 -1.20000 AFIX 0 C2 1 0.148684 0.138136 0.642111 11.00000 0.02824 0.01977 = 0.02150 0.00021 -0.00094 -0.01057 AFIX 43 H2A 2 0.138853 0.061505 0.674979 11.00000 -1.20000 AFIX 0 C3 1 0.092030 0.237078 0.693016 11.00000 0.02478 0.02497 = 0.01671 -0.00198 0.00008 -0.00920 AFIX 43 H3 2 0.041696 0.229750 0.759668 11.00000 -1.20000 AFIX 0 C4 1 0.111054 0.347773 0.643543 11.00000 0.01724 0.02102 = 0.01699 -0.00476 -0.00158 -0.00633 C5 1 0.186052 0.352339 0.544606 11.00000 0.01569 0.01594 = 0.01693 -0.00295 -0.00262 -0.00547 C6 1 0.076957 0.467652 0.666148 11.00000 0.02312 0.02446 = 0.02132 -0.01049 -0.00016 -0.00761 AFIX 43 H6A 2 0.025989 0.495344 0.727325 11.00000 -1.20000 AFIX 0 C7 1 0.131019 0.534571 0.583852 11.00000 0.02218 0.01901 = 0.02564 -0.00881 -0.00250 -0.00665 AFIX 43 H7 2 0.124092 0.617914 0.578668 11.00000 -1.20000 AFIX 0 C8 1 0.468388 0.667431 0.324630 11.00000 0.02276 0.02021 = 0.02148 -0.00540 -0.00609 -0.00461 AFIX 43 H8 2 0.510809 0.630331 0.383155 11.00000 -1.20000 AFIX 0 C9 1 0.480344 0.781704 0.282966 11.00000 0.02341 0.02037 = 0.03312 -0.00728 -0.00466 -0.00797 AFIX 43 H9 2 0.530976 0.822124 0.313496 11.00000 -1.20000 AFIX 0 C10 1 0.420043 0.838320 0.197721 11.00000 0.02535 0.01543 = 0.03049 -0.00175 0.00013 -0.00642 AFIX 43 H10 2 0.428301 0.916924 0.169579 11.00000 -1.20000 AFIX 0 C11 1 0.347196 0.777110 0.154494 11.00000 0.02289 0.01508 = 0.01934 -0.00063 -0.00006 -0.00198 C12 1 0.339210 0.660736 0.199567 11.00000 0.01763 0.01519 = 0.01601 -0.00258 -0.00215 -0.00227 C13 1 0.275399 0.797845 0.068901 11.00000 0.03696 0.02078 = 0.01913 0.00121 -0.00596 -0.00071 AFIX 43 H13 2 0.260650 0.868852 0.022215 11.00000 -1.20000 AFIX 0 C14 1 0.232172 0.697438 0.066593 11.00000 0.03248 0.02496 = 0.02005 -0.00419 -0.01033 0.00169 AFIX 43 H14 2 0.183868 0.686371 0.016341 11.00000 -1.20000 AFIX 0 C15 1 0.286199 0.325637 0.037912 11.00000 0.02254 0.02386 = 0.01930 -0.00139 -0.00235 -0.00702 AFIX 43 H15 2 0.337334 0.386611 0.005743 11.00000 -1.20000 AFIX 0 C16 1 0.233840 0.263407 -0.015936 11.00000 0.02799 0.03079 = 0.01943 -0.00672 -0.00295 -0.00723 AFIX 43 H16 2 0.248535 0.282901 -0.084768 11.00000 -1.20000 AFIX 0 C17 1 0.160391 0.173210 0.028552 11.00000 0.02353 0.02568 = 0.02701 -0.01143 -0.00542 -0.00538 AFIX 43 H17 2 0.126805 0.129604 -0.008961 11.00000 -1.20000 AFIX 0 C18 1 0.137120 0.148159 0.129041 11.00000 0.01691 0.01932 = 0.02674 -0.00830 -0.00423 -0.00338 C19 1 0.190183 0.215859 0.180757 11.00000 0.01507 0.01883 = 0.02014 -0.00436 -0.00310 -0.00366 C20 1 0.070738 0.066251 0.202261 11.00000 0.02022 0.02144 = 0.03251 -0.00684 -0.00325 -0.00779 AFIX 43 H20 2 0.024694 0.007321 0.191857 11.00000 -1.20000 AFIX 0 C21 1 0.085647 0.088234 0.289584 11.00000 0.02021 0.02280 = 0.02852 -0.00232 -0.00170 -0.00874 AFIX 43 H21 2 0.051806 0.045788 0.350793 11.00000 -1.20000 AFIX 0 HKLF 4 REM ow5bl_et2o_0m_a.res in P-1 REM wR2 = 0.038144, GooF = S = 1.16856, Restrained GooF = 1.16880 for all data REM R1 = 0.015913 for 7700 Fo > 4sig(Fo) and 0.016941 for all 7957 data REM 397 parameters refined using 3 restraints END WGHT 0.0097 0.8269 REM Highest difference peak 0.487, deepest hole -0.727, 1-sigma level 0.063 Q1 1 0.1539 0.3433 0.5957 11.00000 0.05 0.49 Q2 1 0.1457 0.1802 0.0797 11.00000 0.05 0.46 Q3 1 0.0986 0.1030 0.1584 11.00000 0.05 0.46 Q4 1 0.7446 0.1219 0.5224 11.00000 0.05 0.43 Q5 1 0.3495 0.7265 0.1777 11.00000 0.05 0.40 Q6 1 0.1832 0.2023 0.2295 11.00000 0.05 0.40 Q7 1 0.2167 0.2744 0.1899 11.00000 0.05 0.40 Q8 1 0.4883 0.7252 0.3017 11.00000 0.05 0.39 Q9 1 0.3040 0.7956 0.1144 11.00000 0.05 0.38 Q10 1 0.1318 0.1795 0.6708 11.00000 0.05 0.38 Q11 1 0.1638 0.1834 0.1517 11.00000 0.05 0.37 Q12 1 0.0969 0.2948 0.6657 11.00000 0.05 0.37 Q13 1 0.2181 0.7607 0.0763 11.00000 0.05 0.37 Q14 1 0.0917 0.3995 0.6573 11.00000 0.05 0.36 Q15 1 0.0592 0.0977 0.2446 11.00000 0.05 0.36 Q16 1 0.2525 0.2979 0.0098 11.00000 0.05 0.36 Q17 1 0.1983 0.1433 0.5982 11.00000 0.05 0.35 Q18 1 0.4173 0.6412 0.3059 11.00000 0.05 0.35 Q19 1 0.0869 0.5069 0.6230 11.00000 0.05 0.35 Q20 1 0.4463 0.8062 0.2446 11.00000 0.05 0.35 ; _shelx_res_checksum 87928 _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 0.52253(2) 0.30180(2) 0.28729(2) 0.01390(2) Uani 1 1 d . . . . . O1 O 0.29507(14) 0.26762(9) 0.40078(7) 0.0191(2) Uani 1 1 d . . . . . O2 O 0.37919(14) 0.49922(9) 0.32371(7) 0.0190(2) Uani 1 1 d . . . . . O3 O 0.31266(14) 0.36123(9) 0.18966(8) 0.0192(2) Uani 1 1 d . . . . . O4 O 0.60001(15) 0.30975(10) 0.44650(8) 0.0238(2) Uani 1 1 d . . . . . O5 O 0.69664(15) 0.13741(10) 0.39113(8) 0.0253(2) Uani 1 1 d . . . . . O6 O 0.7982(2) 0.16613(15) 0.50887(11) 0.0463(4) Uani 1 1 d . . . . . O7 O 0.79040(14) 0.34774(10) 0.25339(8) 0.0212(2) Uani 1 1 d . . . . . O8 O 0.63114(14) 0.43759(10) 0.14610(8) 0.0218(2) Uani 1 1 d . . . . . O9 O 0.88497(15) 0.45013(12) 0.12111(10) 0.0319(3) Uani 1 1 d . . . . . O10 O 0.70231(15) 0.17748(10) 0.16131(8) 0.0235(2) Uani 1 1 d . . . . . O11 O 0.52100(14) 0.09738(10) 0.25581(9) 0.0245(2) Uani 1 1 d . . . . . O12 O 0.70645(18) -0.00411(11) 0.14696(9) 0.0329(3) Uani 1 1 d . . . . . N1 N 0.23603(15) 0.25541(11) 0.49645(9) 0.0160(2) Uani 1 1 d . . . . . N2 N 0.19761(16) 0.46477(11) 0.50853(9) 0.0179(2) Uani 1 1 d D . . . . H2 H 0.244(2) 0.4884(17) 0.4519(11) 0.022 Uiso 1 1 d D U . . . N3 N 0.39714(15) 0.60864(10) 0.28280(9) 0.0160(2) Uani 1 1 d . . . . . N4 N 0.26836(17) 0.61334(12) 0.14779(9) 0.0205(2) Uani 1 1 d D . . . . H4 H 0.266(3) 0.5409(14) 0.1577(15) 0.025 Uiso 1 1 d D U . . . N5 N 0.26522(15) 0.30042(11) 0.13583(9) 0.0179(2) Uani 1 1 d . . . . . N6 N 0.15710(16) 0.18120(12) 0.27673(10) 0.0202(2) Uani 1 1 d D . . . . H6 H 0.184(2) 0.2073(18) 0.3221(13) 0.024 Uiso 1 1 d D U . . . N7 N 0.70068(18) 0.20289(13) 0.45130(10) 0.0243(3) Uani 1 1 d . . . . . N8 N 0.77274(16) 0.41321(11) 0.17174(9) 0.0191(2) Uani 1 1 d . . . . . N9 N 0.64453(17) 0.08743(11) 0.18682(9) 0.0200(2) Uani 1 1 d . . . . . C1 C 0.21925(19) 0.14796(13) 0.54461(11) 0.0203(3) Uani 1 1 d . . . . . H1 H 0.256119 0.078613 0.511365 0.024 Uiso 1 1 calc R U . . . C2 C 0.1487(2) 0.13814(14) 0.64211(11) 0.0233(3) Uani 1 1 d . . . . . H2A H 0.138853 0.061505 0.674979 0.028 Uiso 1 1 calc R U . . . C3 C 0.0920(2) 0.23708(14) 0.69302(11) 0.0224(3) Uani 1 1 d . . . . . H3 H 0.041696 0.229750 0.759668 0.027 Uiso 1 1 calc R U . . . C4 C 0.11105(18) 0.34777(13) 0.64354(10) 0.0182(3) Uani 1 1 d . . . . . C5 C 0.18605(17) 0.35234(12) 0.54461(10) 0.0159(2) Uani 1 1 d . . . . . C6 C 0.0770(2) 0.46765(14) 0.66615(11) 0.0224(3) Uani 1 1 d . . . . . H6A H 0.025989 0.495344 0.727325 0.027 Uiso 1 1 calc R U . . . C7 C 0.13102(19) 0.53457(14) 0.58385(12) 0.0216(3) Uani 1 1 d . . . . . H7 H 0.124092 0.617914 0.578668 0.026 Uiso 1 1 calc R U . . . C8 C 0.46839(19) 0.66743(14) 0.32463(11) 0.0212(3) Uani 1 1 d . . . . . H8 H 0.510809 0.630331 0.383155 0.025 Uiso 1 1 calc R U . . . C9 C 0.4803(2) 0.78170(14) 0.28297(13) 0.0248(3) Uani 1 1 d . . . . . H9 H 0.530976 0.822124 0.313496 0.030 Uiso 1 1 calc R U . . . C10 C 0.4200(2) 0.83832(14) 0.19772(12) 0.0247(3) Uani 1 1 d . . . . . H10 H 0.428301 0.916924 0.169579 0.030 Uiso 1 1 calc R U . . . C11 C 0.34720(19) 0.77711(13) 0.15449(11) 0.0209(3) Uani 1 1 d . . . . . C12 C 0.33921(18) 0.66074(12) 0.19957(10) 0.0170(2) Uani 1 1 d . . . . . C13 C 0.2754(2) 0.79785(15) 0.06890(12) 0.0280(3) Uani 1 1 d . . . . . H13 H 0.260650 0.868852 0.022215 0.034 Uiso 1 1 calc R U . . . C14 C 0.2322(2) 0.69744(15) 0.06659(12) 0.0273(3) Uani 1 1 d . . . . . H14 H 0.183868 0.686371 0.016341 0.033 Uiso 1 1 calc R U . . . C15 C 0.2862(2) 0.32564(14) 0.03791(11) 0.0223(3) Uani 1 1 d . . . . . H15 H 0.337334 0.386611 0.005743 0.027 Uiso 1 1 calc R U . . . C16 C 0.2338(2) 0.26341(16) -0.01594(12) 0.0261(3) Uani 1 1 d . . . . . H16 H 0.248535 0.282901 -0.084768 0.031 Uiso 1 1 calc R U . . . C17 C 0.1604(2) 0.17321(15) 0.02855(12) 0.0246(3) Uani 1 1 d . . . . . H17 H 0.126805 0.129604 -0.008961 0.029 Uiso 1 1 calc R U . . . C18 C 0.13712(18) 0.14816(13) 0.12904(12) 0.0207(3) Uani 1 1 d . . . . . C19 C 0.19018(18) 0.21586(13) 0.18076(11) 0.0181(3) Uani 1 1 d . . . . . C20 C 0.0707(2) 0.06625(14) 0.20226(13) 0.0241(3) Uani 1 1 d . . . . . H20 H 0.024694 0.007321 0.191857 0.029 Uiso 1 1 calc R U . . . C21 C 0.0856(2) 0.08823(14) 0.28958(12) 0.0238(3) Uani 1 1 d . . . . . H21 H 0.051806 0.045788 0.350793 0.029 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.01600(3) 0.01242(3) 0.01326(3) -0.00230(2) -0.00176(2) -0.00437(2) O1 0.0236(5) 0.0212(5) 0.0134(5) -0.0046(4) 0.0024(4) -0.0100(4) O2 0.0265(5) 0.0120(4) 0.0169(5) -0.0001(3) -0.0014(4) -0.0061(4) O3 0.0232(5) 0.0183(5) 0.0204(5) -0.0039(4) -0.0075(4) -0.0087(4) O4 0.0285(6) 0.0220(5) 0.0198(5) -0.0046(4) -0.0056(4) -0.0042(4) O5 0.0320(6) 0.0177(5) 0.0240(6) -0.0017(4) -0.0064(5) -0.0039(4) O6 0.0444(8) 0.0554(9) 0.0319(7) -0.0069(6) -0.0232(6) 0.0063(7) O7 0.0247(5) 0.0230(5) 0.0182(5) 0.0015(4) -0.0063(4) -0.0109(4) O8 0.0200(5) 0.0225(5) 0.0206(5) 0.0009(4) -0.0041(4) -0.0051(4) O9 0.0239(6) 0.0350(6) 0.0326(7) 0.0056(5) 0.0021(5) -0.0137(5) O10 0.0286(6) 0.0220(5) 0.0217(5) -0.0070(4) 0.0012(4) -0.0111(4) O11 0.0228(5) 0.0216(5) 0.0296(6) -0.0083(4) 0.0014(4) -0.0081(4) O12 0.0458(8) 0.0219(5) 0.0302(6) -0.0144(5) -0.0003(6) -0.0070(5) N1 0.0171(5) 0.0164(5) 0.0147(5) -0.0029(4) -0.0005(4) -0.0062(4) N2 0.0210(6) 0.0153(5) 0.0181(6) -0.0035(4) -0.0010(5) -0.0071(4) N3 0.0179(5) 0.0128(5) 0.0158(5) -0.0018(4) -0.0013(4) -0.0038(4) N4 0.0251(6) 0.0171(5) 0.0196(6) -0.0036(4) -0.0077(5) -0.0032(5) N5 0.0173(5) 0.0181(5) 0.0195(6) -0.0043(4) -0.0046(4) -0.0049(4) N6 0.0197(6) 0.0232(6) 0.0193(6) -0.0034(5) -0.0025(5) -0.0089(5) N7 0.0252(6) 0.0273(6) 0.0166(6) -0.0004(5) -0.0041(5) -0.0041(5) N8 0.0211(6) 0.0156(5) 0.0193(6) -0.0031(4) -0.0008(5) -0.0052(4) N9 0.0244(6) 0.0180(5) 0.0190(6) -0.0053(4) -0.0065(5) -0.0048(5) C1 0.0246(7) 0.0154(6) 0.0209(7) -0.0026(5) -0.0012(6) -0.0073(5) C2 0.0282(8) 0.0198(7) 0.0215(7) 0.0002(5) -0.0009(6) -0.0106(6) C3 0.0248(7) 0.0250(7) 0.0167(7) -0.0020(5) 0.0001(5) -0.0092(6) C4 0.0172(6) 0.0210(6) 0.0170(6) -0.0048(5) -0.0016(5) -0.0063(5) C5 0.0157(6) 0.0159(6) 0.0169(6) -0.0030(5) -0.0026(5) -0.0055(5) C6 0.0231(7) 0.0245(7) 0.0213(7) -0.0105(6) -0.0002(6) -0.0076(6) C7 0.0222(7) 0.0190(6) 0.0256(7) -0.0088(5) -0.0025(6) -0.0067(5) C8 0.0228(7) 0.0202(6) 0.0215(7) -0.0054(5) -0.0061(6) -0.0046(5) C9 0.0234(7) 0.0204(7) 0.0331(8) -0.0073(6) -0.0047(6) -0.0080(6) C10 0.0253(7) 0.0154(6) 0.0305(8) -0.0017(5) 0.0001(6) -0.0064(6) C11 0.0229(7) 0.0151(6) 0.0193(7) -0.0006(5) -0.0001(5) -0.0020(5) C12 0.0176(6) 0.0152(6) 0.0160(6) -0.0026(5) -0.0021(5) -0.0023(5) C13 0.0370(9) 0.0208(7) 0.0191(7) 0.0012(5) -0.0060(6) -0.0007(6) C14 0.0325(8) 0.0250(7) 0.0200(7) -0.0042(6) -0.0103(6) 0.0017(6) C15 0.0225(7) 0.0239(7) 0.0193(7) -0.0014(5) -0.0024(5) -0.0070(6) C16 0.0280(8) 0.0308(8) 0.0194(7) -0.0067(6) -0.0029(6) -0.0072(6) C17 0.0235(7) 0.0257(7) 0.0270(8) -0.0114(6) -0.0054(6) -0.0054(6) C18 0.0169(6) 0.0193(6) 0.0267(7) -0.0083(5) -0.0042(5) -0.0034(5) C19 0.0151(6) 0.0188(6) 0.0201(7) -0.0044(5) -0.0031(5) -0.0037(5) C20 0.0202(7) 0.0214(7) 0.0325(8) -0.0068(6) -0.0032(6) -0.0078(6) C21 0.0202(7) 0.0228(7) 0.0285(8) -0.0023(6) -0.0017(6) -0.0087(6) 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' 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 O1 Eu1 O2 79.36(4) . . ? O1 Eu1 O3 78.84(4) . . ? O1 Eu1 O4 77.39(4) . . ? O1 Eu1 O5 85.45(4) . . ? O1 Eu1 O7 148.60(4) . . ? O1 Eu1 O8 148.04(4) . . ? O1 Eu1 O10 128.58(4) . . ? O1 Eu1 O11 77.57(4) . . ? O2 Eu1 O3 78.85(4) . . ? O2 Eu1 O4 74.85(4) . . ? O2 Eu1 O5 125.84(4) . . ? O2 Eu1 O7 90.55(4) . . ? O2 Eu1 O8 75.40(4) . . ? O2 Eu1 O10 145.58(4) . . ? O2 Eu1 O11 150.44(4) . . ? O3 Eu1 O4 147.23(4) . . ? O3 Eu1 O5 147.69(4) . . ? O3 Eu1 O7 128.59(4) . . ? O3 Eu1 O8 77.31(4) . . ? O3 Eu1 O10 86.95(4) . . ? O3 Eu1 O11 78.76(4) . . ? O4 Eu1 O11 117.21(4) . . ? O5 Eu1 O4 51.08(4) . . ? O5 Eu1 O8 125.40(4) . . ? O5 Eu1 O11 70.33(4) . . ? O7 Eu1 O4 71.27(4) . . ? O7 Eu1 O5 76.51(4) . . ? O7 Eu1 O8 51.44(3) . . ? O7 Eu1 O10 74.08(4) . . ? O7 Eu1 O11 118.59(4) . . ? O8 Eu1 O4 113.75(4) . . ? O8 Eu1 O11 117.72(4) . . ? O10 Eu1 O4 125.64(4) . . ? O10 Eu1 O5 81.04(4) . . ? O10 Eu1 O8 70.93(4) . . ? O10 Eu1 O11 51.13(4) . . ? N1 O1 Eu1 142.50(9) . . ? N3 O2 Eu1 132.61(8) . . ? N5 O3 Eu1 132.67(8) . . ? N7 O4 Eu1 94.47(8) . . ? N7 O5 Eu1 96.95(8) . . ? N8 O7 Eu1 97.53(8) . . ? N8 O8 Eu1 94.50(8) . . ? N9 O10 Eu1 97.81(8) . . ? N9 O11 Eu1 94.33(8) . . ? O1 N1 C1 120.81(12) . . ? O1 N1 C5 119.84(11) . . ? C5 N1 C1 119.29(12) . . ? C5 N2 H2 127.6(13) . . ? C5 N2 C7 106.85(12) . . ? C7 N2 H2 125.4(13) . . ? C8 N3 O2 121.38(12) . . ? C12 N3 O2 118.98(12) . . ? C12 N3 C8 119.62(12) . . ? C12 N4 H4 125.0(14) . . ? C12 N4 C14 106.84(13) . . ? C14 N4 H4 127.1(14) . . ? O3 N5 C15 121.45(12) . . ? C19 N5 O3 119.13(12) . . ? C19 N5 C15 119.38(13) . . ? C19 N6 H6 126.4(13) . . ? C19 N6 C21 107.15(13) . . ? C21 N6 H6 126.2(13) . . ? O4 N7 O5 116.15(13) . . ? O6 N7 O4 121.81(15) . . ? O6 N7 O5 122.02(14) . . ? O7 N8 O8 116.15(12) . . ? O9 N8 O7 121.83(13) . . ? O9 N8 O8 122.02(13) . . ? O11 N9 O10 116.53(12) . . ? O12 N9 O10 121.36(14) . . ? O12 N9 O11 122.11(13) . . ? N1 C1 H1 119.8 . . ? N1 C1 C2 120.36(14) . . ? C2 C1 H1 119.8 . . ? C1 C2 H2A 119.2 . . ? C1 C2 C3 121.67(14) . . ? C3 C2 H2A 119.2 . . ? C2 C3 H3 121.0 . . ? C2 C3 C4 117.96(14) . . ? C4 C3 H3 121.0 . . ? C3 C4 C5 118.05(13) . . ? C3 C4 C6 136.92(14) . . ? C5 C4 C6 105.02(13) . . ? N1 C5 N2 126.96(13) . . ? N1 C5 C4 122.63(13) . . ? N2 C5 C4 110.41(12) . . ? C4 C6 H6A 126.5 . . ? C7 C6 C4 107.09(13) . . ? C7 C6 H6A 126.5 . . ? N2 C7 H7 124.7 . . ? C6 C7 N2 110.64(13) . . ? C6 C7 H7 124.7 . . ? N3 C8 H8 119.8 . . ? N3 C8 C9 120.37(14) . . ? C9 C8 H8 119.8 . . ? C8 C9 H9 119.3 . . ? C8 C9 C10 121.33(15) . . ? C10 C9 H9 119.3 . . ? C9 C10 H10 120.9 . . ? C9 C10 C11 118.15(14) . . ? C11 C10 H10 120.9 . . ? C10 C11 C12 118.21(14) . . ? C10 C11 C13 137.02(15) . . ? C12 C11 C13 104.74(14) . . ? N3 C12 N4 126.98(13) . . ? N3 C12 C11 122.32(13) . . ? N4 C12 C11 110.71(13) . . ? C11 C13 H13 126.4 . . ? C14 C13 C11 107.30(14) . . ? C14 C13 H13 126.4 . . ? N4 C14 H14 124.8 . . ? C13 C14 N4 110.39(14) . . ? C13 C14 H14 124.8 . . ? N5 C15 H15 119.8 . . ? N5 C15 C16 120.49(15) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 119.4 . . ? C15 C16 C17 121.24(15) . . ? C17 C16 H16 119.4 . . ? C16 C17 H17 120.8 . . ? C18 C17 C16 118.33(15) . . ? C18 C17 H17 120.8 . . ? C17 C18 C19 118.17(14) . . ? C17 C18 C20 137.04(15) . . ? C19 C18 C20 104.78(14) . . ? N5 C19 C18 122.35(14) . . ? N6 C19 N5 127.15(14) . . ? N6 C19 C18 110.49(13) . . ? C18 C20 H20 126.4 . . ? C21 C20 C18 107.23(14) . . ? C21 C20 H20 126.4 . . ? N6 C21 H21 124.8 . . ? C20 C21 N6 110.33(14) . . ? C20 C21 H21 124.8 . . ? 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 O1 2.3295(10) . ? Eu1 O2 2.3390(10) . ? Eu1 O3 2.3566(10) . ? Eu1 O4 2.5238(11) . ? Eu1 O5 2.4696(11) . ? Eu1 O7 2.4523(11) . ? Eu1 O8 2.5154(11) . ? Eu1 O10 2.4573(11) . ? Eu1 O11 2.5321(11) . ? O1 N1 1.3389(15) . ? O2 N3 1.3452(15) . ? O3 N5 1.3439(15) . ? O4 N7 1.2668(17) . ? O5 N7 1.2706(18) . ? O6 N7 1.2175(18) . ? O7 N8 1.2701(16) . ? O8 N8 1.2707(17) . ? O9 N8 1.2144(17) . ? O10 N9 1.2684(17) . ? O11 N9 1.2645(17) . ? O12 N9 1.2206(16) . ? N1 C1 1.3483(18) . ? N1 C5 1.3432(18) . ? N2 H2 0.851(14) . ? N2 C5 1.3467(18) . ? N2 C7 1.3825(19) . ? N3 C8 1.3431(19) . ? N3 C12 1.3411(18) . ? N4 H4 0.841(15) . ? N4 C12 1.3428(19) . ? N4 C14 1.384(2) . ? N5 C15 1.3493(19) . ? N5 C19 1.3401(19) . ? N6 H6 0.869(15) . ? N6 C19 1.3395(19) . ? N6 C21 1.383(2) . ? C1 H1 0.9500 . ? C1 C2 1.383(2) . ? C2 H2A 0.9500 . ? C2 C3 1.383(2) . ? C3 H3 0.9500 . ? C3 C4 1.393(2) . ? C4 C5 1.409(2) . ? C4 C6 1.427(2) . ? C6 H6A 0.9500 . ? C6 C7 1.356(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C8 C9 1.383(2) . ? C9 H9 0.9500 . ? C9 C10 1.384(2) . ? C10 H10 0.9500 . ? C10 C11 1.387(2) . ? C11 C12 1.4075(19) . ? C11 C13 1.427(2) . ? C13 H13 0.9500 . ? C13 C14 1.355(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C15 C16 1.382(2) . ? C16 H16 0.9500 . ? C16 C17 1.384(2) . ? C17 H17 0.9500 . ? C17 C18 1.384(2) . ? C18 C19 1.413(2) . ? C18 C20 1.427(2) . ? C20 H20 0.9500 . ? C20 C21 1.358(2) . ? C21 H21 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 O2 0.851(14) 1.938(15) 2.7697(16) 165.6(19) . yes N4 H4 O3 0.841(15) 1.992(15) 2.8168(16) 167(2) . yes N6 H6 O1 0.869(15) 1.971(15) 2.8217(17) 165.8(19) . 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 -112.95(15) . . . . ? Eu1 O1 N1 C5 69.89(18) . . . . ? Eu1 O2 N3 C8 -104.31(14) . . . . ? Eu1 O2 N3 C12 77.11(16) . . . . ? Eu1 O3 N5 C15 -113.26(14) . . . . ? Eu1 O3 N5 C19 69.08(16) . . . . ? Eu1 O4 N7 O5 -11.35(14) . . . . ? Eu1 O4 N7 O6 167.10(15) . . . . ? Eu1 O5 N7 O4 11.65(14) . . . . ? Eu1 O5 N7 O6 -166.79(15) . . . . ? Eu1 O7 N8 O8 6.27(13) . . . . ? Eu1 O7 N8 O9 -173.61(12) . . . . ? Eu1 O8 N8 O7 -6.08(12) . . . . ? Eu1 O8 N8 O9 173.80(13) . . . . ? Eu1 O10 N9 O11 4.45(13) . . . . ? Eu1 O10 N9 O12 -175.02(12) . . . . ? Eu1 O11 N9 O10 -4.29(13) . . . . ? Eu1 O11 N9 O12 175.18(13) . . . . ? O1 N1 C1 C2 -176.05(14) . . . . ? O1 N1 C5 N2 -4.6(2) . . . . ? O1 N1 C5 C4 175.07(13) . . . . ? O2 N3 C8 C9 -177.78(13) . . . . ? O2 N3 C12 N4 -2.9(2) . . . . ? O2 N3 C12 C11 177.37(13) . . . . ? O3 N5 C15 C16 -178.87(14) . . . . ? O3 N5 C19 N6 -1.1(2) . . . . ? O3 N5 C19 C18 -179.89(12) . . . . ? N1 C1 C2 C3 0.6(2) . . . . ? N3 C8 C9 C10 -0.1(2) . . . . ? N5 C15 C16 C17 -0.6(2) . . . . ? C1 N1 C5 N2 178.19(14) . . . . ? C1 N1 C5 C4 -2.1(2) . . . . ? C1 C2 C3 C4 -1.3(2) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? C2 C3 C4 C6 -177.96(17) . . . . ? C3 C4 C5 N1 1.4(2) . . . . ? C3 C4 C5 N2 -178.86(13) . . . . ? C3 C4 C6 C7 178.23(18) . . . . ? C4 C6 C7 N2 0.40(18) . . . . ? C5 N1 C1 C2 1.1(2) . . . . ? C5 N2 C7 C6 -0.46(17) . . . . ? C5 C4 C6 C7 -0.19(17) . . . . ? C6 C4 C5 N1 -179.82(13) . . . . ? C6 C4 C5 N2 -0.09(17) . . . . ? C7 N2 C5 N1 -179.95(14) . . . . ? C7 N2 C5 C4 0.33(16) . . . . ? C8 N3 C12 N4 178.50(14) . . . . ? C8 N3 C12 C11 -1.2(2) . . . . ? C8 C9 C10 C11 -0.2(2) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? C9 C10 C11 C13 -178.01(18) . . . . ? C10 C11 C12 N3 0.9(2) . . . . ? C10 C11 C12 N4 -178.83(14) . . . . ? C10 C11 C13 C14 177.31(19) . . . . ? C11 C13 C14 N4 1.5(2) . . . . ? C12 N3 C8 C9 0.8(2) . . . . ? C12 N4 C14 C13 -1.74(19) . . . . ? C12 C11 C13 C14 -0.69(18) . . . . ? C13 C11 C12 N3 179.39(14) . . . . ? C13 C11 C12 N4 -0.39(17) . . . . ? C14 N4 C12 N3 -178.48(15) . . . . ? C14 N4 C12 C11 1.28(17) . . . . ? C15 N5 C19 N6 -178.85(14) . . . . ? C15 N5 C19 C18 2.4(2) . . . . ? C15 C16 C17 C18 1.3(2) . . . . ? C16 C17 C18 C19 -0.2(2) . . . . ? C16 C17 C18 C20 -179.50(17) . . . . ? C17 C18 C19 N5 -1.7(2) . . . . ? C17 C18 C19 N6 179.38(13) . . . . ? C17 C18 C20 C21 179.68(18) . . . . ? C18 C20 C21 N6 0.54(18) . . . . ? C19 N5 C15 C16 -1.2(2) . . . . ? C19 N6 C21 C20 -1.24(18) . . . . ? C19 C18 C20 C21 0.32(17) . . . . ? C20 C18 C19 N5 177.82(13) . . . . ? C20 C18 C19 N6 -1.11(16) . . . . ? C21 N6 C19 N5 -177.42(14) . . . . ? C21 N6 C19 C18 1.45(17) . . . . ?