#------------------------------------------------------------------------------ #$Date: 2021-07-31 11:27:07 +0300 (Sat, 31 Jul 2021) $ #$Revision: 267856 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564286.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_1564286 loop_ _publ_author_name 'Boukhemis, Ouafa' 'Bendjeddou, Lamia' 'Platas-Iglesias, Carlos' 'Esteban-G\'omez, David' 'Carcelli, Mauro' 'Merazig, Hocine' _publ_section_title ; Hydrothermal synthesis of six new lanthanides coordination polymers based on 1-H-benzimidazole-5-carboxylic acid: Structure, Hirshfeld analysis, thermal and spectroscopic properties ; _journal_name_full 'Inorganica Chimica Acta' _journal_page_first 119740 _journal_paper_doi 10.1016/j.ica.2020.119740 _journal_volume 510 _journal_year 2020 _chemical_absolute_configuration . _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C24 H17 La N6 O7 ' _chemical_formula_sum 'C24 H17 La N6 O7' _chemical_formula_weight 640.35 _chemical_name_systematic ; Catena-Poly [aqua( \m3-1H-benzimidazole-5-carboxylato \k4 N:O^5^ ,O^5^', O^5^') ( \m2-1H-benzimidazole-5-carboxylato \k2 O^5^ ,O^5^') ( \m2-1H-benzimidazole-5-carboxylato \k2 O^5^ ,O^5^') lantanium(III)] ; _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 105.5610(10) _cell_angle_beta 96.2640(10) _cell_angle_gamma 108.9940(10) _cell_formula_units_Z 2 _cell_length_a 8.9408(2) _cell_length_b 11.7861(3) _cell_length_c 12.1424(3) _cell_measurement_reflns_used 9992 _cell_measurement_temperature 296 _cell_measurement_theta_max 35.02 _cell_measurement_theta_min 4.29 _cell_volume 1138.10(5) _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEPIII (Farrugia, 2012)' _computing_publication_material ; WinGX (Farrugia, 2012), Mercury (Version 1.4; Macrae et al., 2006) and POVRay (Persistence of Vision Team, 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SIR2002 (Burla et al, 2003)' _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_unetI/netI 0.0093 _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 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 22250 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 5.081 _exptl_absorpt_coefficient_mu 1.939 _exptl_absorpt_correction_T_max 0.7469 _exptl_absorpt_correction_T_min 0.7035 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014) was used for absorption correction. wR2(int) was 0.0632 before and 0.0252 after correction. The Ratio of minimum to maximum transmission is 0.8295. The \l/2 correction factor is 0.00150. ; _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.407 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 349 _refine_ls_number_reflns 4597 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.091 _refine_ls_R_factor_all 0.0130 _refine_ls_R_factor_gt 0.0128 _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^)+(0.0168P)^2^+0.7817P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0344 _reflns_number_gt 4530 _reflns_number_total 4597 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ICA-2020-510-119740.cif _cod_data_source_block 1 _cod_original_formula_sum 'C24 H17 La N6 O7 ' _cod_database_code 1564286 _shelx_res_file ; TITL lamia_La_0m_a_a.res in P-1 lamia_La_0m_a.res created by SHELXL-2018/3 at 10:51:22 on 27-Oct-2019 CELL 0.71073 8.9408 11.7861 12.1424 105.561 96.264 108.994 ZERR 2 0.0002 0.0003 0.0003 0.001 0.001 0.001 LATT 1 SFAC C H La N O UNIT 48 34 2 12 14 DFIX 0.85 0.01 H1W O1W DFIX 0.85 0.01 H2W O1W DFIX 1.39 H1W H2W L.S. 4 PLAN 4 TEMP 23 BOND LIST 4 fmap 2 acta MERG 2 SHEL 50 0.8 OMIT -3 -1 1 OMIT 1 0 0 OMIT -1 0 2 OMIT 1 -1 2 OMIT 1 0 1 OMIT 0 -2 2 OMIT 1 1 0 OMIT 0 1 1 OMIT 0 2 0 OMIT -1 0 1 OMIT -1 1 2 OMIT -1 -1 2 OMIT 0 -2 1 OMIT 0 -1 2 OMIT 1 -2 1 OMIT 0 0 2 OMIT -1 1 1 OMIT 1 -1 1 OMIT -1 2 0 OMIT 0 1 0 OMIT 0 0 1 OMIT 0 -1 1 OMIT -1 1 0 OMIT -1 -1 1 OMIT -1 -3 7 OMIT 1 1 1 OMIT 3 -4 2 OMIT -2 1 3 OMIT 3 -4 4 OMIT 0 2 6 OMIT -1 -5 3 OMIT -4 5 0 OMIT 0 3 1 OMIT 1 0 2 OMIT 2 -2 1 OMIT 0 -7 3 OMIT 4 -7 5 OMIT 2 0 0 OMIT 1 -5 3 OMIT 0 -1 3 OMIT -2 1 5 OMIT 1 -3 1 OMIT 1 2 0 OMIT -2 2 1 OMIT -1 0 3 OMIT -1 -1 3 WGHT 0.016800 0.781700 FVAR 0.69036 LA1 3 0.231461 0.116225 0.511542 11.00000 0.00655 0.00838 = 0.01207 0.00472 0.00103 0.00286 O1W 5 0.364259 0.004925 0.369159 11.00000 0.01592 0.01349 = 0.01676 0.00721 0.00551 0.00864 AFIX 2 H1W 2 0.403714 -0.047841 0.368376 11.00000 -1.50000 H2W 2 0.374670 0.020174 0.309797 11.00000 -1.50000 AFIX 0 O4 5 0.436895 0.338078 0.692051 11.00000 0.01203 0.01371 = 0.02225 0.00798 0.00239 0.00600 O3 5 0.500311 0.168466 0.643957 11.00000 0.01066 0.01143 = 0.01660 0.00403 0.00018 0.00431 O5 5 -0.098836 0.105841 0.493254 11.00000 0.01371 0.01160 = 0.01768 0.00725 0.00371 0.00600 O2 5 -0.066674 -0.047795 0.693278 11.00000 0.01149 0.02304 = 0.01447 0.00587 0.00041 0.00505 N6 4 -0.467432 0.438557 0.358910 11.00000 0.01295 0.01217 = 0.01813 0.00873 0.00323 0.00695 AFIX 43 H6N 2 -0.464530 0.498441 0.330414 11.00000 -1.20000 AFIX 0 O7 5 0.110747 0.274569 0.500984 11.00000 0.00896 0.01277 = 0.02440 0.00749 0.00147 0.00457 N3 4 1.128472 0.363492 0.819816 11.00000 0.01246 0.01566 = 0.01920 0.00427 0.00072 0.00514 AFIX 43 H3N 2 1.138303 0.291678 0.792047 11.00000 -1.20000 AFIX 0 O1 5 0.141120 0.122762 0.697919 11.00000 0.01772 0.01672 = 0.01459 0.00755 0.00398 0.00776 N5 4 -0.566661 0.279977 0.430496 11.00000 0.01005 0.01261 = 0.01647 0.00655 0.00337 0.00570 C18 1 -0.150188 0.274639 0.442256 11.00000 0.01039 0.00976 = 0.01194 0.00346 0.00070 0.00414 N4 4 1.200309 0.571525 0.913032 11.00000 0.01268 0.01735 = 0.01693 0.00581 -0.00025 0.00078 C23 1 -0.308544 0.235672 0.457168 11.00000 0.01021 0.00976 = 0.01214 0.00536 0.00194 0.00336 AFIX 43 H23 2 -0.349186 0.169026 0.486260 11.00000 -1.20000 AFIX 0 N1 4 0.547476 0.192018 1.074230 11.00000 0.01286 0.01523 = 0.01564 0.00371 -0.00045 0.00165 AFIX 43 H1N 2 0.620865 0.253859 1.063237 11.00000 -1.20000 AFIX 0 C19 1 -0.089314 0.374524 0.396103 11.00000 0.00929 0.01207 = 0.01319 0.00455 0.00233 0.00241 AFIX 43 H19 2 0.016920 0.397993 0.386196 11.00000 -1.20000 AFIX 0 C22 1 -0.404726 0.299693 0.427115 11.00000 0.00911 0.01071 = 0.01118 0.00337 0.00149 0.00326 N2 4 0.427407 0.050803 1.160140 11.00000 0.01785 0.01899 = 0.01298 0.00420 -0.00004 0.00773 C24 1 -0.596303 0.364826 0.389104 11.00000 0.01150 0.01414 = 0.01829 0.00707 0.00345 0.00673 AFIX 43 H24 2 -0.696467 0.373219 0.381377 11.00000 -1.20000 AFIX 0 C14 1 0.986472 0.386906 0.811938 11.00000 0.01299 0.01485 = 0.01355 0.00596 0.00241 0.00510 C21 1 -0.341666 0.399395 0.382531 11.00000 0.01258 0.00946 = 0.01127 0.00308 0.00066 0.00560 C15 1 0.827421 0.308609 0.756835 11.00000 0.01363 0.01173 = 0.01451 0.00330 0.00111 0.00295 AFIX 43 H15 2 0.799208 0.222488 0.718480 11.00000 -1.20000 AFIX 0 C17 1 -0.040070 0.214583 0.480831 11.00000 0.01230 0.01111 = 0.01091 0.00360 0.00283 0.00598 C7 1 0.316565 0.125396 0.900957 11.00000 0.01544 0.01416 = 0.01478 0.00637 0.00311 0.00410 AFIX 43 H7 2 0.365121 0.186295 0.867239 11.00000 -1.20000 AFIX 0 C2 1 0.162312 0.034083 0.850207 11.00000 0.01301 0.01550 = 0.01264 0.00454 0.00227 0.00612 C20 1 -0.183542 0.437844 0.365490 11.00000 0.01199 0.00958 = 0.01289 0.00505 0.00227 0.00209 AFIX 43 H20 2 -0.143558 0.503290 0.334837 11.00000 -1.20000 AFIX 0 C16 1 1.248886 0.476103 0.879929 11.00000 0.01086 0.02056 = 0.01814 0.00706 -0.00001 0.00222 AFIX 43 H16 2 1.357016 0.485223 0.896446 11.00000 -1.20000 AFIX 0 C3 1 0.090597 -0.059444 0.901207 11.00000 0.01310 0.01575 = 0.01749 0.00501 0.00062 0.00188 AFIX 43 H3 2 -0.010943 -0.121453 0.863732 11.00000 -1.20000 AFIX 0 C4 1 0.168026 -0.060587 1.005218 11.00000 0.01738 0.01670 = 0.01853 0.00895 0.00360 0.00349 AFIX 43 H4 2 0.119497 -0.121490 1.038940 11.00000 -1.20000 AFIX 0 C13 1 1.033214 0.517622 0.870724 11.00000 0.01325 0.01358 = 0.01236 0.00429 0.00091 0.00078 C8 1 0.559106 0.144942 1.163304 11.00000 0.01643 0.01799 = 0.01235 0.00075 -0.00104 0.00771 AFIX 43 H8 2 0.652179 0.176308 1.221909 11.00000 -1.20000 AFIX 0 C1 1 0.071301 0.035050 0.739776 11.00000 0.01291 0.01614 = 0.01205 0.00370 0.00355 0.00839 C11 1 0.757492 0.495364 0.821405 11.00000 0.01600 0.01506 = 0.01669 0.00581 0.00296 0.00747 AFIX 43 H11 2 0.678182 0.530539 0.824199 11.00000 -1.20000 AFIX 0 C10 1 0.712159 0.364462 0.761454 11.00000 0.01160 0.01324 = 0.01237 0.00523 0.00127 0.00284 C12 1 0.916154 0.572564 0.875962 11.00000 0.01929 0.01053 = 0.01656 0.00281 0.00161 0.00357 AFIX 43 H12 2 0.944162 0.658514 0.914993 11.00000 -1.20000 AFIX 0 C6 1 0.394641 0.121434 1.004190 11.00000 0.01245 0.01295 = 0.01518 0.00264 0.00198 0.00348 C9 1 0.540030 0.286832 0.697044 11.00000 0.01215 0.01387 = 0.01174 0.00702 0.00301 0.00484 C5 1 0.321805 0.032590 1.058579 11.00000 0.01605 0.01550 = 0.01224 0.00418 0.00210 0.00740 HKLF 4 REM lamia_La_0m_a_a.res in P-1 REM wR2 = 0.0339, GooF = S = 1.091, Restrained GooF = 1.091 for all data REM R1 = 0.0128 for 4530 Fo > 4sig(Fo) and 0.0130 for all 4597 data REM 349 parameters refined using 0 restraints END WGHT 0.0168 0.7819 REM Highest difference peak 0.407, deepest hole -0.300, 1-sigma level 0.056 Q1 1 -0.3025 0.3511 0.5390 11.00000 0.05 0.41 Q2 1 0.1818 0.0648 0.4380 11.00000 0.05 0.39 Q3 1 0.2645 0.1568 0.5921 11.00000 0.05 0.38 Q4 1 0.2179 0.1196 0.5833 11.00000 0.05 0.37 ; loop_ _symmetry_equiv_pos_as_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 La1 La 0.23146(2) 0.11623(2) 0.51154(2) 0.00876(3) Uani 1 1 d . . . . . O1W O 0.36426(13) 0.00492(10) 0.36916(10) 0.0139(2) Uani 1 1 d . . . . . H1W H 0.404(2) -0.048(2) 0.3684(18) 0.021 Uiso 1 1 d . . . . . H2W H 0.375(2) 0.0202(19) 0.3098(19) 0.021 Uiso 1 1 d . . . . . O4 O 0.43690(12) 0.33808(10) 0.69205(9) 0.0153(2) Uani 1 1 d . . . . . O3 O 0.50031(12) 0.16847(9) 0.64396(9) 0.0132(2) Uani 1 1 d . . . . . O5 O -0.09884(12) 0.10584(9) 0.49325(9) 0.0134(2) Uani 1 1 d . . . . . O2 O -0.06667(12) -0.04780(10) 0.69328(9) 0.0169(2) Uani 1 1 d . . . . . N6 N -0.46743(15) 0.43856(11) 0.35891(11) 0.0130(2) Uani 1 1 d . . . . . H6N H -0.464530 0.498441 0.330414 0.016 Uiso 1 1 calc R . . . . O7 O 0.11075(12) 0.27457(10) 0.50098(9) 0.0151(2) Uani 1 1 d . . . . . N3 N 1.12847(15) 0.36349(12) 0.81982(11) 0.0163(3) Uani 1 1 d . . . . . H3N H 1.138303 0.291678 0.792047 0.020 Uiso 1 1 calc R . . . . O1 O 0.14112(13) 0.12276(10) 0.69792(9) 0.0154(2) Uani 1 1 d . . . . . N5 N -0.56666(14) 0.27998(11) 0.43050(11) 0.0122(2) Uani 1 1 d . . . . . C18 C -0.15019(17) 0.27464(13) 0.44226(12) 0.0107(3) Uani 1 1 d . . . . . N4 N 1.20031(15) 0.57153(12) 0.91303(11) 0.0171(3) Uani 1 1 d . . . . . C23 C -0.30854(16) 0.23567(13) 0.45717(12) 0.0104(3) Uani 1 1 d . . . . . H23 H -0.349186 0.169026 0.486260 0.013 Uiso 1 1 calc R . . . . N1 N 0.54748(15) 0.19202(12) 1.07423(11) 0.0161(3) Uani 1 1 d . . . . . H1N H 0.620865 0.253859 1.063237 0.019 Uiso 1 1 calc R . . . . C19 C -0.08931(17) 0.37452(13) 0.39610(12) 0.0118(3) Uani 1 1 d . . . . . H19 H 0.016920 0.397993 0.386196 0.014 Uiso 1 1 calc R . . . . C22 C -0.40473(16) 0.29969(13) 0.42712(12) 0.0105(3) Uani 1 1 d . . . . . N2 N 0.42741(16) 0.05080(12) 1.16014(11) 0.0169(3) Uani 1 1 d . . . . . C24 C -0.59630(17) 0.36483(13) 0.38910(13) 0.0137(3) Uani 1 1 d . . . . . H24 H -0.696467 0.373219 0.381377 0.016 Uiso 1 1 calc R . . . . C14 C 0.98647(17) 0.38691(14) 0.81194(12) 0.0136(3) Uani 1 1 d . . . . . C21 C -0.34167(17) 0.39939(13) 0.38253(12) 0.0109(3) Uani 1 1 d . . . . . C15 C 0.82742(17) 0.30861(14) 0.75684(13) 0.0141(3) Uani 1 1 d . . . . . H15 H 0.799208 0.222488 0.718480 0.017 Uiso 1 1 calc R . . . . C17 C -0.04007(17) 0.21458(13) 0.48083(12) 0.0110(3) Uani 1 1 d . . . . . C7 C 0.31657(18) 0.12540(14) 0.90096(13) 0.0148(3) Uani 1 1 d . . . . . H7 H 0.365121 0.186295 0.867239 0.018 Uiso 1 1 calc R . . . . C2 C 0.16231(17) 0.03408(14) 0.85021(12) 0.0135(3) Uani 1 1 d . . . . . C20 C -0.18354(17) 0.43784(13) 0.36549(12) 0.0117(3) Uani 1 1 d . . . . . H20 H -0.143558 0.503290 0.334837 0.014 Uiso 1 1 calc R . . . . C16 C 1.24889(18) 0.47610(15) 0.87993(13) 0.0176(3) Uani 1 1 d . . . . . H16 H 1.357016 0.485223 0.896446 0.021 Uiso 1 1 calc R . . . . C3 C 0.09060(18) -0.05944(14) 0.90121(13) 0.0167(3) Uani 1 1 d . . . . . H3 H -0.010943 -0.121453 0.863732 0.020 Uiso 1 1 calc R . . . . C4 C 0.16803(19) -0.06059(14) 1.00522(13) 0.0176(3) Uani 1 1 d . . . . . H4 H 0.119497 -0.121490 1.038940 0.021 Uiso 1 1 calc R . . . . C13 C 1.03321(18) 0.51762(14) 0.87072(12) 0.0143(3) Uani 1 1 d . . . . . C8 C 0.55911(18) 0.14494(14) 1.16330(13) 0.0165(3) Uani 1 1 d . . . . . H8 H 0.652179 0.176308 1.221909 0.020 Uiso 1 1 calc R . . . . C1 C 0.07130(17) 0.03505(14) 0.73978(12) 0.0130(3) Uani 1 1 d . . . . . C11 C 0.75749(18) 0.49536(14) 0.82141(13) 0.0154(3) Uani 1 1 d . . . . . H11 H 0.678182 0.530539 0.824199 0.018 Uiso 1 1 calc R . . . . C10 C 0.71216(17) 0.36446(13) 0.76145(12) 0.0127(3) Uani 1 1 d . . . . . C12 C 0.91615(19) 0.57256(14) 0.87596(13) 0.0165(3) Uani 1 1 d . . . . . H12 H 0.944162 0.658514 0.914993 0.020 Uiso 1 1 calc R . . . . C6 C 0.39464(17) 0.12143(14) 1.00419(13) 0.0143(3) Uani 1 1 d . . . . . C9 C 0.54003(17) 0.28683(13) 0.69704(12) 0.0119(3) Uani 1 1 d . . . . . C5 C 0.32181(18) 0.03259(14) 1.05858(12) 0.0143(3) 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 La1 0.0066(1) 0.0084(1) 0.0121(1) 0.0047(1) 0.0010(1) 0.0029(1) O1 0.0177(5) 0.0167(5) 0.0146(5) 0.0076(4) 0.0040(4) 0.0078(4) O1W 0.0159(5) 0.0135(5) 0.0168(5) 0.0072(4) 0.0055(4) 0.0086(4) O2 0.0115(5) 0.0230(5) 0.0145(5) 0.0059(4) 0.0004(4) 0.0050(4) O3 0.0107(5) 0.0114(5) 0.0166(5) 0.0040(4) 0.0002(4) 0.0043(4) O4 0.0120(5) 0.0137(5) 0.0223(5) 0.0080(4) 0.0024(4) 0.0060(4) O5 0.0137(5) 0.0116(5) 0.0177(5) 0.0073(4) 0.0037(4) 0.0060(4) O7 0.0090(5) 0.0128(5) 0.0244(5) 0.0075(4) 0.0015(4) 0.0046(4) N1 0.0129(6) 0.0152(6) 0.0156(6) 0.0037(5) -0.0005(5) 0.0017(5) N2 0.0179(6) 0.0190(6) 0.0130(6) 0.0042(5) 0.0000(5) 0.0077(5) N3 0.0125(6) 0.0157(6) 0.0192(6) 0.0043(5) 0.0007(5) 0.0051(5) N4 0.0127(6) 0.0174(6) 0.0169(6) 0.0058(5) -0.0002(5) 0.0008(5) N5 0.0101(6) 0.0126(6) 0.0165(6) 0.0065(5) 0.0034(4) 0.0057(5) N6 0.0130(6) 0.0122(6) 0.0181(6) 0.0087(5) 0.0032(5) 0.0070(5) C1 0.0129(7) 0.0161(7) 0.0120(6) 0.0037(5) 0.0035(5) 0.0084(6) C2 0.0130(7) 0.0155(7) 0.0126(7) 0.0045(5) 0.0023(5) 0.0061(6) C3 0.0131(7) 0.0157(7) 0.0175(7) 0.0050(6) 0.0006(6) 0.0019(6) C4 0.0174(7) 0.0167(7) 0.0185(7) 0.0090(6) 0.0036(6) 0.0035(6) C5 0.0161(7) 0.0155(7) 0.0122(6) 0.0042(5) 0.0021(5) 0.0074(6) C6 0.0124(7) 0.0130(7) 0.0152(7) 0.0026(5) 0.0020(5) 0.0035(5) C7 0.0154(7) 0.0142(7) 0.0148(7) 0.0064(5) 0.0031(5) 0.0041(6) C8 0.0164(7) 0.0180(7) 0.0124(7) 0.0007(6) -0.0010(5) 0.0077(6) C9 0.0122(7) 0.0139(7) 0.0117(6) 0.0070(5) 0.0030(5) 0.0048(5) C10 0.0116(7) 0.0132(7) 0.0124(6) 0.0052(5) 0.0013(5) 0.0028(5) C11 0.0160(7) 0.0151(7) 0.0167(7) 0.0058(6) 0.0030(6) 0.0075(6) C12 0.0193(7) 0.0105(6) 0.0166(7) 0.0028(5) 0.0016(6) 0.0036(6) C13 0.0132(7) 0.0136(7) 0.0124(7) 0.0043(5) 0.0009(5) 0.0008(5) C14 0.0130(7) 0.0148(7) 0.0136(7) 0.0060(5) 0.0024(5) 0.0051(6) C15 0.0136(7) 0.0117(6) 0.0145(7) 0.0033(5) 0.0011(5) 0.0029(5) C16 0.0109(7) 0.0206(7) 0.0181(7) 0.0071(6) 0.0000(6) 0.0022(6) C17 0.0123(6) 0.0111(6) 0.0109(6) 0.0036(5) 0.0028(5) 0.0060(5) C18 0.0104(6) 0.0098(6) 0.0119(6) 0.0035(5) 0.0007(5) 0.0041(5) C19 0.0093(6) 0.0121(6) 0.0132(6) 0.0045(5) 0.0023(5) 0.0024(5) C20 0.0120(6) 0.0096(6) 0.0129(6) 0.0051(5) 0.0023(5) 0.0021(5) C21 0.0126(6) 0.0095(6) 0.0113(6) 0.0031(5) 0.0007(5) 0.0056(5) C22 0.0091(6) 0.0107(6) 0.0112(6) 0.0034(5) 0.0015(5) 0.0033(5) C23 0.0102(6) 0.0098(6) 0.0121(6) 0.0054(5) 0.0019(5) 0.0034(5) C24 0.0115(6) 0.0141(7) 0.0183(7) 0.0071(6) 0.0035(5) 0.0067(5) 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 La1 O1W 142.60(4) . . . yes O1 La1 O3 80.93(4) . . . yes O1 La1 O4 69.64(4) . . . yes O1 La1 O5 67.85(3) . . . yes O1 La1 O7 86.54(4) . . . yes O1 La1 N5 136.22(4) . . 1_655 yes O1 La1 O2 129.74(4) . . 2_556 yes O1 La1 O5 72.51(4) . . 2_556 yes O1W La1 O3 79.61(4) . . . yes O1W La1 O4 116.93(4) . . . yes O1W La1 O5 131.46(3) . . . yes O1W La1 O7 130.73(4) . . . yes O1W La1 N5 69.49(4) . . 1_655 yes O1W La1 O2 70.86(4) . . 2_556 yes O1W La1 O5 79.11(4) . . 2_556 yes O3 La1 O4 48.23(3) . . . yes O3 La1 O5 147.42(3) . . . yes O3 La1 O7 123.65(4) . . . yes O3 La1 N5 78.49(4) . . 1_655 yes O2 La1 O3 148.52(4) 2_556 . . yes O3 La1 O5 98.32(4) . . 2_556 yes O4 La1 O5 109.07(3) . . . yes O4 La1 O7 75.86(3) . . . yes O4 La1 N5 67.78(4) . . 1_655 yes O2 La1 O4 140.25(4) 2_556 . . yes O4 La1 O5 132.32(3) . . 2_556 yes O5 La1 O7 48.00(3) . . . yes O5 La1 N5 117.92(4) . . 1_655 yes O2 La1 O5 64.01(3) 2_556 . . yes O5 La1 O5 81.46(3) . . 2_556 yes O7 La1 N5 73.81(4) . . 1_655 yes O2 La1 O7 72.01(4) 2_556 . . yes O5 La1 O7 129.45(4) 2_556 . . yes O2 La1 N5 81.12(4) 2_556 . 1_655 yes O5 La1 N5 148.53(4) 2_556 . 1_655 yes O2 La1 O5 86.82(4) 2_556 . 2_556 yes La1 O1 C1 132.22(10) . . . yes La1 O2 C1 129.82(10) 2_556 . . yes La1 O3 C9 101.54(9) . . . yes La1 O4 C9 88.44(9) . . . yes La1 O5 C17 83.99(9) . . . yes La1 O5 La1 98.55(4) . . 2_556 yes La1 O5 C17 172.10(9) 2_556 . . yes La1 O7 C17 104.68(10) . . . yes C6 N1 C8 106.60(13) . . . yes La1 O1W H2W 121.1(15) . . . no H1W O1W H2W 105(2) . . . no La1 O1W H1W 134.2(15) . . . no C5 N2 C8 103.98(13) . . . yes C14 N3 C16 106.33(13) . . . yes C13 N4 C16 104.21(13) . . . yes La1 N5 C24 127.18(10) 1_455 . . yes C22 N5 C24 104.52(13) . . . yes La1 N5 C22 128.24(10) 1_455 . . yes C21 N6 C24 106.88(13) . . . yes O1 C1 O2 123.50(14) . . . yes O1 C1 C2 117.17(14) . . . yes C6 N1 H1N 127.00 . . . no C8 N1 H1N 127.00 . . . no O2 C1 C2 119.33(14) . . . yes C1 C2 C3 119.69(14) . . . no C1 C2 C7 119.21(14) . . . no C3 C2 C7 121.11(14) . . . no C16 N3 H3N 127.00 . . . no C14 N3 H3N 127.00 . . . no C2 C3 C4 121.40(15) . . . no C3 C4 C5 118.02(15) . . . no N2 C5 C6 110.06(14) . . . yes N2 C5 C4 129.91(15) . . . yes C4 C5 C6 119.93(14) . . . no N1 C6 C5 105.03(13) . . . yes N1 C6 C7 132.40(15) . . . yes C5 C6 C7 122.56(15) . . . no C21 N6 H6N 127.00 . . . no C24 N6 H6N 127.00 . . . no C2 C7 C6 116.88(15) . . . no N1 C8 N2 114.30(14) . . . yes O3 C9 O4 120.21(14) . . . yes O3 C9 C10 119.10(14) . . . yes O4 C9 C10 120.65(13) . . . yes C9 C10 C11 119.70(14) . . . no C9 C10 C15 119.76(13) . . . no C11 C10 C15 120.46(15) . . . no C10 C11 C12 121.96(15) . . . no C11 C12 C13 118.02(15) . . . no C12 C13 C14 119.56(15) . . . no N4 C13 C14 109.69(14) . . . yes N4 C13 C12 130.74(15) . . . yes N3 C14 C15 131.77(15) . . . yes C13 C14 C15 122.84(15) . . . no N3 C14 C13 105.34(14) . . . yes C10 C15 C14 117.16(14) . . . no N3 C16 N4 114.43(15) . . . yes O5 C17 O7 121.78(14) . . . yes O7 C17 C18 118.19(14) . . . yes O5 C17 C18 120.03(14) . . . yes C17 C18 C19 119.37(14) . . . no C17 C18 C23 119.49(13) . . . no C19 C18 C23 121.07(14) . . . no C18 C19 C20 121.57(15) . . . no C19 C20 C21 116.96(14) . . . no C20 C21 C22 122.29(14) . . . no N6 C21 C22 105.54(13) . . . yes N6 C21 C20 132.12(14) . . . yes N5 C22 C23 130.34(14) . . . yes N5 C22 C21 109.37(13) . . . yes C21 C22 C23 120.27(14) . . . no C18 C23 C22 117.83(14) . . . no N5 C24 N6 113.70(14) . . . yes C2 C3 H3 119.00 . . . no C4 C3 H3 119.00 . . . no C3 C4 H4 121.00 . . . no C5 C4 H4 121.00 . . . no C2 C7 H7 122.00 . . . no C6 C7 H7 122.00 . . . no N1 C8 H8 123.00 . . . no N2 C8 H8 123.00 . . . no C10 C11 H11 119.00 . . . no C12 C11 H11 119.00 . . . no C11 C12 H12 121.00 . . . no C13 C12 H12 121.00 . . . no C10 C15 H15 121.00 . . . no C14 C15 H15 121.00 . . . no N3 C16 H16 123.00 . . . no N4 C16 H16 123.00 . . . no C18 C19 H19 119.00 . . . no C20 C19 H19 119.00 . . . no C19 C20 H20 122.00 . . . no C21 C20 H20 122.00 . . . no C18 C23 H23 121.00 . . . no C22 C23 H23 121.00 . . . no N5 C24 H24 123.00 . . . no N6 C24 H24 123.00 . . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag La1 O1 2.4751(11) . . yes La1 O1W 2.5229(12) . . yes La1 O3 2.5307(11) . . yes La1 O4 2.8169(11) . . yes La1 O5 2.8969(12) . . yes La1 O7 2.4644(12) . . yes La1 N5 2.6627(13) . 1_655 yes La1 O2 2.5213(11) . 2_556 yes La1 O5 2.4785(11) . 2_556 yes O1 C1 1.284(2) . . yes O2 C1 1.2498(19) . . yes O3 C9 1.2778(18) . . yes O4 C9 1.260(2) . . yes O5 C17 1.2744(19) . . yes O7 C17 1.262(2) . . yes N1 C6 1.382(2) . . yes N1 C8 1.350(2) . . yes O1W H1W 0.81(2) . . no O1W H2W 0.80(2) . . no N2 C8 1.318(2) . . yes N2 C5 1.389(2) . . yes N3 C14 1.383(2) . . yes N3 C16 1.354(2) . . yes N4 C16 1.315(2) . . yes N4 C13 1.393(2) . . yes N5 C22 1.397(2) . . yes N5 C24 1.318(2) . . yes N6 C21 1.378(2) . . yes N6 C24 1.352(2) . . yes N1 H1N 0.8600 . . no C1 C2 1.496(2) . . no C2 C7 1.390(2) . . no C2 C3 1.415(2) . . no C3 C4 1.378(2) . . no N3 H3N 0.8600 . . no C4 C5 1.399(2) . . no C5 C6 1.406(2) . . no N6 H6N 0.8600 . . no C6 C7 1.387(2) . . no C9 C10 1.501(2) . . no C10 C11 1.414(2) . . no C10 C15 1.390(2) . . no C11 C12 1.382(2) . . no C12 C13 1.397(2) . . no C13 C14 1.408(2) . . no C14 C15 1.389(2) . . no C17 C18 1.490(2) . . no C18 C19 1.414(2) . . no C18 C23 1.388(2) . . no C19 C20 1.377(2) . . no C20 C21 1.394(2) . . no C21 C22 1.403(2) . . no C22 C23 1.394(2) . . no C3 H3 0.9300 . . no C4 H4 0.9300 . . no C7 H7 0.9300 . . no C8 H8 0.9300 . . no C11 H11 0.9300 . . no C12 H12 0.9300 . . no C15 H15 0.9300 . . no C16 H16 0.9300 . . no C19 H19 0.9300 . . no C20 H20 0.9300 . . no C23 H23 0.9300 . . no C24 H24 0.9300 . . no 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 N1 H1N N4 0.8600 2.0800 2.912(2) 163.00 2_767 yes N3 H3N O1 0.8600 2.0200 2.8716(18) 169.00 1_655 yes N6 H6N O4 0.8600 1.9600 2.7984(17) 165.00 2_566 yes O1W H1W O3 0.81(2) 1.86(2) 2.6732(16) 176.00 2_656 yes O1W H2W N2 0.80(2) 2.02(2) 2.8112(17) 172.00 1_554 yes C15 H15 O1W 0.9300 2.4600 3.347(2) 161.00 2_656 yes C23 H23 O3 0.9300 2.4600 3.1018(18) 126.00 1_455 yes C8 H8 Cg6 0.9300 2.4100 3.1432(16) 136.00 1_656 yes C20 H20 Cg2 0.9300 2.5100 3.2772(16) 140.00 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 O1W La1 O1 C1 -40.13(17) . . . . no O3 La1 O1 C1 -99.50(14) . . . . no O4 La1 O1 C1 -148.17(14) . . . . no O5 La1 O1 C1 89.99(14) . . . . no O7 La1 O1 C1 135.63(14) . . . . no N5 La1 O1 C1 -162.20(13) 1_655 . . . no O2 La1 O1 C1 72.54(15) 2_556 . . . no O5 La1 O1 C1 2.28(13) 2_556 . . . no O1 La1 O3 C9 -77.81(9) . . . . no O1W La1 O3 C9 134.28(9) . . . . no O4 La1 O3 C9 -7.07(8) . . . . no O5 La1 O3 C9 -61.34(11) . . . . no O7 La1 O3 C9 1.84(10) . . . . no N5 La1 O3 C9 63.33(9) 1_655 . . . no O2 La1 O3 C9 113.96(10) 2_556 . . . no O5 La1 O3 C9 -148.48(9) 2_556 . . . no O1 La1 O4 C9 103.12(9) . . . . no O1W La1 O4 C9 -36.52(9) . . . . no O3 La1 O4 C9 7.03(8) . . . . no O5 La1 O4 C9 159.48(8) . . . . no O7 La1 O4 C9 -165.33(9) . . . . no N5 La1 O4 C9 -87.32(9) 1_655 . . . no O2 La1 O4 C9 -128.55(9) 2_556 . . . no O5 La1 O4 C9 63.62(10) 2_556 . . . no O1 La1 O5 C17 113.03(8) . . . . no O1 La1 O5 La1 -74.51(4) . . . 2_556 no O1W La1 O5 C17 -105.26(8) . . . . no O1W La1 O5 La1 67.20(5) . . . 2_556 no O3 La1 O5 C17 95.44(9) . . . . no O3 La1 O5 La1 -92.11(6) . . . 2_556 no O4 La1 O5 C17 55.60(8) . . . . no O4 La1 O5 La1 -131.94(3) . . . 2_556 no O7 La1 O5 C17 6.83(7) . . . . no O7 La1 O5 La1 179.29(6) . . . 2_556 no N5 La1 O5 C17 -18.76(9) 1_655 . . . no N5 La1 O5 La1 153.70(4) 1_655 . . 2_556 no O2 La1 O5 C17 -81.83(8) 2_556 . . . no O2 La1 O5 La1 90.63(4) 2_556 . . 2_556 no O5 La1 O5 C17 -172.46(8) 2_556 . . . no O5 La1 O5 La1 0.00(3) 2_556 . . 2_556 no O1 La1 O7 C17 -70.09(9) . . . . no O1W La1 O7 C17 106.51(9) . . . . no O3 La1 O7 C17 -146.80(8) . . . . no O4 La1 O7 C17 -139.95(9) . . . . no O5 La1 O7 C17 -7.09(8) . . . . no N5 La1 O7 C17 149.49(9) 1_655 . . . no O2 La1 O7 C17 63.78(9) 2_556 . . . no O5 La1 O7 C17 -6.18(10) 2_556 . . . no O1 La1 N5 C22 95.38(12) . . 1_655 1_655 no O1 La1 N5 C24 -81.36(13) . . 1_655 1_655 no O1W La1 N5 C22 -51.29(11) . . 1_655 1_655 no O1W La1 N5 C24 131.98(13) . . 1_655 1_655 no O3 La1 N5 C22 31.80(11) . . 1_655 1_655 no O3 La1 N5 C24 -144.94(13) . . 1_655 1_655 no O4 La1 N5 C22 81.17(12) . . 1_655 1_655 no O4 La1 N5 C24 -95.56(13) . . 1_655 1_655 no O5 La1 N5 C22 -178.28(11) . . 1_655 1_655 no O5 La1 N5 C24 4.98(13) . . 1_655 1_655 no O7 La1 N5 C22 162.19(12) . . 1_655 1_655 no O7 La1 N5 C24 -14.55(12) . . 1_655 1_655 no O1 La1 O2 C1 -32.34(15) . . 2_556 2_556 no O1W La1 O2 C1 111.27(14) . . 2_556 2_556 no O3 La1 O2 C1 132.48(13) . . 2_556 2_556 no O4 La1 O2 C1 -139.32(12) . . 2_556 2_556 no O5 La1 O2 C1 -50.34(13) . . 2_556 2_556 no O7 La1 O2 C1 -101.70(14) . . 2_556 2_556 no O1 La1 O5 La1 69.36(4) . . 2_556 2_556 no O1W La1 O5 La1 -135.29(4) . . 2_556 2_556 no O3 La1 O5 La1 147.05(3) . . 2_556 2_556 no O4 La1 O5 La1 108.06(4) . . 2_556 2_556 no O5 La1 O5 La1 0.00(3) . . 2_556 2_556 no O7 La1 O5 La1 -0.69(6) . . 2_556 2_556 no La1 O1 C1 O2 -62.9(2) . . . . no La1 O1 C1 C2 117.18(13) . . . . no La1 O2 C1 O1 17.1(2) 2_556 . . . no La1 O2 C1 C2 -163.02(10) 2_556 . . . no La1 O3 C9 O4 13.74(15) . . . . no La1 O3 C9 C10 -164.04(11) . . . . no La1 O4 C9 O3 -12.07(13) . . . . no La1 O4 C9 C10 165.67(12) . . . . no La1 O5 C17 O7 -11.71(13) . . . . no La1 O5 C17 C18 168.67(12) . . . . no La1 O7 C17 O5 14.20(15) . . . . no La1 O7 C17 C18 -166.18(10) . . . . no C8 N1 C6 C5 -0.08(18) . . . . no C8 N1 C6 C7 -178.99(18) . . . . no C6 N1 C8 N2 -0.98(19) . . . . no C8 N2 C5 C4 174.65(17) . . . . no C8 N2 C5 C6 -1.56(18) . . . . no C5 N2 C8 N1 1.57(19) . . . . no C16 N3 C14 C13 -0.18(16) . . . . no C16 N3 C14 C15 177.29(16) . . . . no C14 N3 C16 N4 0.31(18) . . . . no C16 N4 C13 C12 -178.07(16) . . . . no C16 N4 C13 C14 0.16(17) . . . . no C13 N4 C16 N3 -0.29(18) . . . . no C24 N5 C22 C21 0.18(16) . . . . no C24 N5 C22 C23 -178.07(15) . . . . no La1 N5 C22 C21 -177.14(9) 1_455 . . . no La1 N5 C22 C23 4.6(2) 1_455 . . . no C22 N5 C24 N6 -0.03(17) . . . . no La1 N5 C24 N6 177.32(9) 1_455 . . . no C24 N6 C21 C20 177.55(15) . . . . no C24 N6 C21 C22 0.22(15) . . . . no C21 N6 C24 N5 -0.12(17) . . . . no O1 C1 C2 C3 179.23(14) . . . . no O1 C1 C2 C7 -0.9(2) . . . . no O2 C1 C2 C3 -0.7(2) . . . . no O2 C1 C2 C7 179.21(15) . . . . no C1 C2 C3 C4 -177.52(15) . . . . no C7 C2 C3 C4 2.6(2) . . . . no C1 C2 C7 C6 179.04(14) . . . . no C3 C2 C7 C6 -1.1(2) . . . . no C2 C3 C4 C5 -1.1(2) . . . . no C3 C4 C5 N2 -177.73(16) . . . . no C3 C4 C5 C6 -1.8(2) . . . . no N2 C5 C6 N1 1.03(18) . . . . no N2 C5 C6 C7 -179.93(15) . . . . no C4 C5 C6 N1 -175.62(15) . . . . no C4 C5 C6 C7 3.4(2) . . . . no N1 C6 C7 C2 176.84(16) . . . . no C5 C6 C7 C2 -1.9(2) . . . . no O3 C9 C10 C11 -179.47(13) . . . . no O3 C9 C10 C15 3.7(2) . . . . no O4 C9 C10 C11 2.8(2) . . . . no O4 C9 C10 C15 -174.03(14) . . . . no C9 C10 C11 C12 -175.98(14) . . . . no C15 C10 C11 C12 0.8(2) . . . . no C9 C10 C15 C14 176.04(13) . . . . no C11 C10 C15 C14 -0.7(2) . . . . no C10 C11 C12 C13 -0.1(2) . . . . no C11 C12 C13 N4 177.42(15) . . . . no C11 C12 C13 C14 -0.7(2) . . . . no N4 C13 C14 N3 0.00(18) . . . . no N4 C13 C14 C15 -177.74(14) . . . . no C12 C13 C14 N3 178.47(13) . . . . no C12 C13 C14 C15 0.7(2) . . . . no N3 C14 C15 C10 -177.10(15) . . . . no C13 C14 C15 C10 0.0(2) . . . . no O5 C17 C18 C19 -161.58(13) . . . . no O5 C17 C18 C23 21.4(2) . . . . no O7 C17 C18 C19 18.8(2) . . . . no O7 C17 C18 C23 -158.27(13) . . . . no C17 C18 C19 C20 -176.25(13) . . . . no C23 C18 C19 C20 0.8(2) . . . . no C17 C18 C23 C22 175.89(13) . . . . no C19 C18 C23 C22 -1.1(2) . . . . no C18 C19 C20 C21 0.3(2) . . . . no C19 C20 C21 N6 -177.86(15) . . . . no C19 C20 C21 C22 -0.9(2) . . . . no N6 C21 C22 N5 -0.25(16) . . . . no N6 C21 C22 C23 178.20(13) . . . . no C20 C21 C22 N5 -177.90(13) . . . . no C20 C21 C22 C23 0.6(2) . . . . no N5 C22 C23 C18 178.57(14) . . . . no C21 C22 C23 C18 0.5(2) . . . . no