#------------------------------------------------------------------------------ #$Date: 2021-07-31 11:27:07 +0300 (Sat, 31 Jul 2021) $ #$Revision: 267856 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564287.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_1564287 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 N6 O7 Pr ' _chemical_formula_sum 'C24 H17 N6 O7 Pr' _chemical_formula_weight 642.34 _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^')praseodymium(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 104.556(2) _cell_angle_beta 97.038(2) _cell_angle_gamma 109.275(2) _cell_formula_units_Z 2 _cell_length_a 8.9084(4) _cell_length_b 11.7747(5) _cell_length_c 12.2291(6) _cell_measurement_reflns_used 9866 _cell_measurement_temperature 296 _cell_measurement_theta_max 34.98 _cell_measurement_theta_min 2.99 _cell_volume 1141.96(9) _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 0.976 _diffrn_measured_fraction_theta_max 0.979 _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 0.0228 _diffrn_reflns_av_unetI/netI 0.0181 _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 21056 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 4.555 _exptl_absorpt_coefficient_mu 2.195 _exptl_absorpt_correction_T_max 0.7469 _exptl_absorpt_correction_T_min 0.6873 _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 1.865 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 636 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _refine_diff_density_max 2.307 _refine_diff_density_min -0.892 _refine_diff_density_rms 0.114 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.230 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 349 _refine_ls_number_reflns 4586 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.230 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0308 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.00 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'W=1/[\S^2^(FO^2^)+6.7316P] WHERE P=(FO^2^+2FC^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.0807 _reflns_number_gt 4416 _reflns_number_total 4586 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ICA-2020-510-119740.cif _cod_data_source_block 2 _cod_database_code 1564287 _shelx_res_file ; TITL Lamia_pr_0m_a.res in P-1 Lamia_pr_0m_a.res created by SHELXL-2018/3 at 16:39:47 on 31-Oct-2019 CELL 0.71073 8.9084 11.7747 12.2291 104.556 97.038 109.275 ZERR 2 0.0004 0.0005 0.0006 0.002 0.002 0.002 LATT 1 SFAC C H Pr 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 20 TEMP 23 BOND $H LIST 4 fmap 2 acta MERG 2 SHEL 50 0.8 OMIT 0 0 1 OMIT 0 1 0 OMIT 0 -1 1 OMIT 0 -2 1 OMIT 0 -3 6 OMIT 0 -3 9 OMIT 1 -1 6 OMIT 0 -3 10 OMIT 0 -3 8 OMIT 1 -1 1 OMIT 2 -4 1 OMIT 0 1 3 OMIT -2 0 2 OMIT 2 -4 2 OMIT 0 3 0 OMIT -2 1 1 OMIT -3 3 5 OMIT -3 3 5 OMIT 1 0 0 OMIT 2 -3 2 OMIT 2 -2 2 OMIT 1 1 2 WGHT 0.000000 6.731600 FVAR 0.67902 PR1 5 0.231932 0.116405 0.511756 11.00000 0.01185 0.01426 = 0.02217 0.00832 0.00258 0.00431 O7 4 0.108643 0.270947 0.503067 11.00000 0.01798 0.01992 = 0.04180 0.01251 0.00153 0.00637 O4 4 0.437423 0.334317 0.687896 11.00000 0.02159 0.02183 = 0.04124 0.01483 0.00340 0.00934 O3 4 0.498985 0.165121 0.641282 11.00000 0.01687 0.02217 = 0.02818 0.00509 -0.00150 0.00758 O5 4 -0.102303 0.102097 0.493232 11.00000 0.02471 0.01555 = 0.03317 0.01284 0.00833 0.00863 O1W 4 0.360222 0.006508 0.372236 11.00000 0.02866 0.02271 = 0.03024 0.01159 0.00792 0.01344 AFIX 2 H1W 2 0.420356 -0.034850 0.380660 11.00000 -1.50000 H2W 2 0.366843 0.026884 0.310639 11.00000 -1.50000 AFIX 0 O2 4 -0.066635 -0.049937 0.686929 11.00000 0.01875 0.03885 = 0.02420 0.01059 0.00132 0.00739 O1 4 0.144504 0.120820 0.693229 11.00000 0.03119 0.02882 = 0.02220 0.01099 0.00474 0.01039 N6 3 -0.469190 0.438279 0.359917 11.00000 0.02422 0.02342 = 0.03313 0.01771 0.00663 0.01257 AFIX 43 H6N 2 -0.466581 0.498435 0.331365 11.00000 -1.20000 AFIX 0 N4 3 1.205355 0.568197 0.911126 11.00000 0.02214 0.02971 = 0.03009 0.00910 -0.00079 -0.00114 N5 3 -0.569921 0.278183 0.430426 11.00000 0.01559 0.02223 = 0.03047 0.01179 0.00627 0.00878 C7 1 0.315745 0.122852 0.899148 11.00000 0.02434 0.02581 = 0.02529 0.01056 0.00548 0.00414 AFIX 43 H7 2 0.366766 0.183900 0.865912 11.00000 -1.20000 AFIX 0 N2 3 0.418948 0.047520 1.158942 11.00000 0.03531 0.03439 = 0.01905 0.00810 0.00094 0.01213 C21 1 -0.341980 0.399164 0.383632 11.00000 0.02070 0.01681 = 0.02220 0.00897 0.00285 0.00789 N1 3 0.542878 0.190232 1.074987 11.00000 0.02349 0.02820 = 0.02846 0.00648 -0.00065 0.00231 AFIX 43 H1N 2 0.617292 0.252748 1.064947 11.00000 -1.20000 AFIX 0 N3 3 1.133551 0.361399 0.818372 11.00000 0.02306 0.02607 = 0.03691 0.00731 0.00142 0.00725 AFIX 43 H3N 2 1.143666 0.290208 0.790834 11.00000 -1.20000 AFIX 0 C11 1 0.760258 0.490056 0.818931 11.00000 0.03045 0.02256 = 0.03039 0.00790 0.00491 0.01128 AFIX 43 H11 2 0.680519 0.524876 0.821432 11.00000 -1.20000 AFIX 0 C2 1 0.160499 0.031453 0.846331 11.00000 0.01946 0.02681 = 0.02142 0.00729 0.00433 0.00825 C6 1 0.390695 0.118827 1.003209 11.00000 0.02354 0.02282 = 0.02199 0.00387 0.00105 0.00438 C22 1 -0.406545 0.298389 0.427732 11.00000 0.01825 0.01721 = 0.02401 0.01013 0.00783 0.00682 C19 1 -0.089907 0.374037 0.397887 11.00000 0.01400 0.02104 = 0.02667 0.00993 0.00473 0.00345 AFIX 43 H19 2 0.017345 0.398331 0.389311 11.00000 -1.20000 AFIX 0 C12 1 0.918855 0.566946 0.873570 11.00000 0.03224 0.02053 = 0.03343 0.00652 0.00475 0.00646 AFIX 43 H12 2 0.946741 0.652200 0.913056 11.00000 -1.20000 AFIX 0 C13 1 1.036851 0.513363 0.868073 11.00000 0.02541 0.02191 = 0.02191 0.00661 0.00187 0.00124 C24 1 -0.598389 0.364111 0.390085 11.00000 0.01811 0.02529 = 0.03324 0.01342 0.00471 0.01152 AFIX 43 H24 2 -0.698625 0.373177 0.382887 11.00000 -1.20000 AFIX 0 C3 1 0.087029 -0.062284 0.896651 11.00000 0.02260 0.02834 = 0.02817 0.00778 -0.00121 0.00224 AFIX 43 H3 2 -0.014545 -0.124831 0.857984 11.00000 -1.20000 AFIX 0 C20 1 -0.184483 0.437239 0.366606 11.00000 0.02179 0.01792 = 0.02450 0.01082 0.00428 0.00611 AFIX 43 H20 2 -0.144499 0.502621 0.335415 11.00000 -1.20000 AFIX 0 C10 1 0.713381 0.359663 0.758865 11.00000 0.02289 0.02196 = 0.02058 0.00757 0.00303 0.00598 C5 1 0.315365 0.028733 1.056081 11.00000 0.02736 0.02926 = 0.01992 0.00778 0.00323 0.01117 C4 1 0.161969 -0.063667 1.001907 11.00000 0.03152 0.03068 = 0.03111 0.01772 0.00453 0.00263 AFIX 43 H4 2 0.111190 -0.124587 1.035344 11.00000 -1.20000 AFIX 0 C18 1 -0.152443 0.272672 0.442913 11.00000 0.01478 0.01400 = 0.02229 0.00462 0.00027 0.00325 C14 1 0.990523 0.383651 0.810503 11.00000 0.02111 0.02269 = 0.02327 0.00710 0.00131 0.00589 C23 1 -0.309946 0.234167 0.457772 11.00000 0.01734 0.01383 = 0.02331 0.00772 0.00295 0.00603 AFIX 43 H23 2 -0.350716 0.167254 0.487002 11.00000 -1.20000 AFIX 0 C16 1 1.254564 0.473856 0.878009 11.00000 0.02052 0.03879 = 0.03413 0.01270 0.00119 0.00390 AFIX 43 H16 2 1.363704 0.483704 0.894288 11.00000 -1.20000 AFIX 0 C15 1 0.829719 0.305326 0.754893 11.00000 0.02182 0.01818 = 0.02718 0.00486 0.00039 0.00317 AFIX 43 H15 2 0.801453 0.219745 0.716519 11.00000 -1.20000 AFIX 0 C17 1 -0.039540 0.212953 0.482054 11.00000 0.02479 0.02106 = 0.01796 0.00848 0.00702 0.01474 C8 1 0.552099 0.143171 1.163379 11.00000 0.03017 0.03416 = 0.02109 0.00027 -0.00388 0.01269 AFIX 43 H8 2 0.644690 0.175155 1.223122 11.00000 -1.20000 AFIX 0 C9 1 0.540224 0.283185 0.693788 11.00000 0.02010 0.02353 = 0.02422 0.01278 0.00473 0.00859 C1 1 0.071673 0.032518 0.734417 11.00000 0.02166 0.02571 = 0.02256 0.00588 0.00467 0.01054 HKLF 4 REM Lamia_pr_0m_a.res in P-1 REM wR2 = 0.0807, GooF = S = 1.230, Restrained GooF = 1.230 for all data REM R1 = 0.0308 for 4416 Fo > 4sig(Fo) and 0.0322 for all 4586 data REM 349 parameters refined using 3 restraints END WGHT 0.0000 6.7316 REM Highest difference peak 2.307, deepest hole -0.892, 1-sigma level 0.114 Q1 1 0.1408 0.2043 0.4979 11.00000 0.05 2.31 Q2 1 -0.4042 0.4291 0.4963 11.00000 0.05 2.00 Q3 1 -0.5000 0.5000 0.5000 10.50000 0.05 1.25 Q4 1 -0.3196 0.3283 0.4821 11.00000 0.05 1.13 Q5 1 0.3141 0.0175 0.4809 11.00000 0.05 0.82 Q6 1 -0.0450 0.3553 0.5224 11.00000 0.05 0.82 Q7 1 0.2112 0.0780 0.4458 11.00000 0.05 0.79 Q8 1 0.2706 0.1989 0.5982 11.00000 0.05 0.62 Q9 1 -0.1406 0.4203 0.4243 11.00000 0.05 0.55 Q10 1 0.4308 0.0764 0.4418 11.00000 0.05 0.49 Q11 1 0.4905 0.0996 0.4373 11.00000 0.05 0.42 Q12 1 -0.3313 0.4999 0.2811 11.00000 0.05 0.42 Q13 1 0.0461 0.2649 0.5208 11.00000 0.05 0.40 Q14 1 0.1170 0.0457 0.7980 11.00000 0.05 0.39 Q15 1 -0.7055 0.1810 0.2799 11.00000 0.05 0.38 Q16 1 -0.1477 -0.0735 0.6372 11.00000 0.05 0.38 Q17 1 -0.1322 0.3138 0.4022 11.00000 0.05 0.37 Q18 1 0.1210 0.2814 0.4560 11.00000 0.05 0.37 Q19 1 -0.2493 0.2613 0.5661 11.00000 0.05 0.37 Q20 1 0.0564 0.1103 0.7073 11.00000 0.05 0.36 ; 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 Pr1 Pr 0.23193(3) 0.11641(2) 0.51176(2) 0.01584(8) Uani 1 1 d . . . . . O7 O 0.1086(4) 0.2709(3) 0.5031(3) 0.0267(7) Uani 1 1 d . . . . . O4 O 0.4374(4) 0.3343(3) 0.6879(3) 0.0273(7) Uani 1 1 d . . . . . O3 O 0.4990(4) 0.1651(3) 0.6413(3) 0.0235(7) Uani 1 1 d . . . . . O5 O -0.1023(4) 0.1021(3) 0.4932(3) 0.0230(7) Uani 1 1 d . . . . . O1W O 0.3602(4) 0.0065(3) 0.3722(3) 0.0254(7) Uani 1 1 d D . . . . H1W H 0.420(6) -0.035(5) 0.381(4) 0.038 Uiso 1 1 d D . . . . H2W H 0.367(7) 0.027(5) 0.311(3) 0.038 Uiso 1 1 d D . . . . O2 O -0.0666(4) -0.0499(3) 0.6869(3) 0.0284(7) Uani 1 1 d . . . . . O1 O 0.1445(4) 0.1208(3) 0.6932(3) 0.0272(7) Uani 1 1 d . . . . . N6 N -0.4692(5) 0.4383(4) 0.3599(4) 0.0242(8) Uani 1 1 d . . . . . H6N H -0.466581 0.498435 0.331365 0.029 Uiso 1 1 calc R . . . . N4 N 1.2054(5) 0.5682(4) 0.9111(4) 0.0309(9) Uani 1 1 d . . . . . N5 N -0.5699(4) 0.2782(4) 0.4304(3) 0.0215(8) Uani 1 1 d . . . . . C7 C 0.3157(6) 0.1229(5) 0.8991(4) 0.0261(10) Uani 1 1 d . . . . . H7 H 0.366766 0.183900 0.865912 0.031 Uiso 1 1 calc R . . . . N2 N 0.4189(5) 0.0475(4) 1.1589(3) 0.0304(9) Uani 1 1 d . . . . . C21 C -0.3420(5) 0.3992(4) 0.3836(4) 0.0193(9) Uani 1 1 d . . . . . N1 N 0.5429(5) 0.1902(4) 1.0750(4) 0.0298(9) Uani 1 1 d . . . . . H1N H 0.617292 0.252748 1.064947 0.036 Uiso 1 1 calc R . . . . N3 N 1.1336(5) 0.3614(4) 0.8184(4) 0.0302(9) Uani 1 1 d . . . . . H3N H 1.143666 0.290208 0.790834 0.036 Uiso 1 1 calc R . . . . C11 C 0.7603(6) 0.4901(4) 0.8189(4) 0.0277(10) Uani 1 1 d . . . . . H11 H 0.680519 0.524876 0.821432 0.033 Uiso 1 1 calc R . . . . C2 C 0.1605(5) 0.0315(4) 0.8463(4) 0.0228(9) Uani 1 1 d . . . . . C6 C 0.3907(6) 0.1188(4) 1.0032(4) 0.0249(10) Uani 1 1 d . . . . . C22 C -0.4065(5) 0.2984(4) 0.4277(4) 0.0188(8) Uani 1 1 d . . . . . C19 C -0.0899(5) 0.3740(4) 0.3979(4) 0.0209(9) Uani 1 1 d . . . . . H19 H 0.017345 0.398331 0.389311 0.025 Uiso 1 1 calc R . . . . C12 C 0.9189(6) 0.5669(5) 0.8736(5) 0.0303(11) Uani 1 1 d . . . . . H12 H 0.946741 0.652200 0.913056 0.036 Uiso 1 1 calc R . . . . C13 C 1.0369(6) 0.5134(4) 0.8681(4) 0.0255(10) Uani 1 1 d . . . . . C24 C -0.5984(6) 0.3641(4) 0.3901(4) 0.0239(9) Uani 1 1 d . . . . . H24 H -0.698625 0.373177 0.382887 0.029 Uiso 1 1 calc R . . . . C3 C 0.0870(6) -0.0623(5) 0.8967(4) 0.0292(11) Uani 1 1 d . . . . . H3 H -0.014545 -0.124831 0.857984 0.035 Uiso 1 1 calc R . . . . C20 C -0.1845(5) 0.4372(4) 0.3666(4) 0.0210(9) Uani 1 1 d . . . . . H20 H -0.144499 0.502621 0.335415 0.025 Uiso 1 1 calc R . . . . C10 C 0.7134(6) 0.3597(4) 0.7589(4) 0.0225(9) Uani 1 1 d . . . . . C5 C 0.3154(6) 0.0287(5) 1.0561(4) 0.0255(10) Uani 1 1 d . . . . . C4 C 0.1620(6) -0.0637(5) 1.0019(5) 0.0322(11) Uani 1 1 d . . . . . H4 H 0.111190 -0.124587 1.035344 0.039 Uiso 1 1 calc R . . . . C18 C -0.1524(5) 0.2727(4) 0.4429(4) 0.0182(8) Uani 1 1 d . . . . . C14 C 0.9905(6) 0.3837(4) 0.8105(4) 0.0233(9) Uani 1 1 d . . . . . C23 C -0.3099(5) 0.2342(4) 0.4578(4) 0.0179(8) Uani 1 1 d . . . . . H23 H -0.350716 0.167254 0.487002 0.021 Uiso 1 1 calc R . . . . C16 C 1.2546(6) 0.4739(5) 0.8780(5) 0.0333(11) Uani 1 1 d . . . . . H16 H 1.363704 0.483704 0.894288 0.040 Uiso 1 1 calc R . . . . C15 C 0.8297(6) 0.3053(4) 0.7549(4) 0.0245(10) Uani 1 1 d . . . . . H15 H 0.801453 0.219745 0.716519 0.029 Uiso 1 1 calc R . . . . C17 C -0.0395(5) 0.2130(4) 0.4821(4) 0.0190(9) Uani 1 1 d . . . . . C8 C 0.5521(6) 0.1432(5) 1.1634(4) 0.0309(11) Uani 1 1 d . . . . . H8 H 0.644690 0.175155 1.223122 0.037 Uiso 1 1 calc R . . . . C9 C 0.5402(5) 0.2832(4) 0.6938(4) 0.0215(9) Uani 1 1 d . . . . . C1 C 0.0717(6) 0.0325(4) 0.7344(4) 0.0232(9) 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 Pr1 0.01185(12) 0.01426(12) 0.02217(13) 0.00832(9) 0.00258(8) 0.00431(8) O7 0.0180(16) 0.0199(16) 0.042(2) 0.0125(15) 0.0015(14) 0.0064(13) O4 0.0216(16) 0.0218(16) 0.041(2) 0.0148(15) 0.0034(14) 0.0093(14) O3 0.0169(15) 0.0222(16) 0.0282(17) 0.0051(13) -0.0015(13) 0.0076(13) O5 0.0247(16) 0.0156(15) 0.0332(18) 0.0128(13) 0.0083(14) 0.0086(13) O1W 0.0287(18) 0.0227(17) 0.0302(18) 0.0116(14) 0.0079(14) 0.0134(14) O2 0.0188(16) 0.039(2) 0.0242(17) 0.0106(15) 0.0013(13) 0.0074(15) O1 0.0312(18) 0.0288(18) 0.0222(16) 0.0110(14) 0.0047(14) 0.0104(15) N6 0.024(2) 0.0234(19) 0.033(2) 0.0177(17) 0.0066(16) 0.0126(16) N4 0.022(2) 0.030(2) 0.030(2) 0.0091(18) -0.0008(17) -0.0011(17) N5 0.0156(18) 0.0222(19) 0.030(2) 0.0118(16) 0.0063(15) 0.0088(15) C7 0.024(2) 0.026(2) 0.025(2) 0.0106(19) 0.0055(19) 0.0041(19) N2 0.035(2) 0.034(2) 0.0190(19) 0.0081(17) 0.0009(17) 0.0121(19) C21 0.021(2) 0.017(2) 0.022(2) 0.0090(17) 0.0029(17) 0.0079(17) N1 0.023(2) 0.028(2) 0.028(2) 0.0065(17) -0.0007(17) 0.0023(17) N3 0.023(2) 0.026(2) 0.037(2) 0.0073(18) 0.0014(17) 0.0072(17) C11 0.030(3) 0.023(2) 0.030(3) 0.008(2) 0.005(2) 0.011(2) C2 0.019(2) 0.027(2) 0.021(2) 0.0073(18) 0.0043(17) 0.0082(19) C6 0.024(2) 0.023(2) 0.022(2) 0.0039(18) 0.0011(18) 0.0044(19) C22 0.018(2) 0.017(2) 0.024(2) 0.0101(17) 0.0078(17) 0.0068(17) C19 0.014(2) 0.021(2) 0.027(2) 0.0099(18) 0.0047(17) 0.0035(17) C12 0.032(3) 0.021(2) 0.033(3) 0.007(2) 0.005(2) 0.006(2) C13 0.025(2) 0.022(2) 0.022(2) 0.0066(18) 0.0019(18) 0.0012(19) C24 0.018(2) 0.025(2) 0.033(3) 0.013(2) 0.0047(18) 0.0115(18) C3 0.023(2) 0.028(2) 0.028(2) 0.008(2) -0.0012(19) 0.002(2) C20 0.022(2) 0.018(2) 0.024(2) 0.0108(18) 0.0043(18) 0.0061(17) C10 0.023(2) 0.022(2) 0.021(2) 0.0076(18) 0.0030(18) 0.0060(18) C5 0.027(2) 0.029(2) 0.020(2) 0.0078(19) 0.0032(18) 0.011(2) C4 0.032(3) 0.031(3) 0.031(3) 0.018(2) 0.005(2) 0.003(2) C18 0.015(2) 0.0140(19) 0.022(2) 0.0046(16) 0.0003(16) 0.0033(16) C14 0.021(2) 0.023(2) 0.023(2) 0.0071(18) 0.0013(18) 0.0059(18) C23 0.017(2) 0.0138(19) 0.023(2) 0.0077(17) 0.0030(16) 0.0060(16) C16 0.021(2) 0.039(3) 0.034(3) 0.013(2) 0.001(2) 0.004(2) C15 0.022(2) 0.018(2) 0.027(2) 0.0049(18) 0.0004(18) 0.0032(18) C17 0.025(2) 0.021(2) 0.018(2) 0.0085(17) 0.0070(17) 0.0147(18) C8 0.030(3) 0.034(3) 0.021(2) 0.000(2) -0.0039(19) 0.013(2) C9 0.020(2) 0.024(2) 0.024(2) 0.0128(18) 0.0047(17) 0.0086(18) C1 0.022(2) 0.026(2) 0.023(2) 0.0059(18) 0.0047(18) 0.0105(19) 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 Pr1 O1W 142.54(12) . . . yes O1 Pr1 O3 80.88(12) . . . yes O1 Pr1 O4 69.55(11) . . . yes O1 Pr1 O7 85.38(12) . . . yes O1 Pr1 N5 136.65(12) . . 1_655 yes O1 Pr1 O2 129.53(12) . . 2_556 yes O1 Pr1 O5 72.95(12) . . 2_556 yes O1W Pr1 O3 79.73(12) . . . yes O1W Pr1 O4 117.53(11) . . . yes O1W Pr1 O7 131.86(12) . . . yes O1W Pr1 N5 69.59(12) . . 1_655 yes O1W Pr1 O2 70.58(12) . . 2_556 yes O1W Pr1 O5 78.26(12) . . 2_556 yes O3 Pr1 O4 48.85(11) . . . yes O3 Pr1 O7 124.38(12) . . . yes O3 Pr1 N5 79.28(12) . . 1_655 yes O2 Pr1 O3 148.59(12) 2_556 . . yes O3 Pr1 O5 97.63(12) . . 2_556 yes O4 Pr1 O7 75.82(11) . . . yes O4 Pr1 N5 68.32(11) . . 1_655 yes O2 Pr1 O4 140.50(11) 2_556 . . yes O4 Pr1 O5 132.51(11) . . 2_556 yes O7 Pr1 N5 74.97(12) . . 1_655 yes O2 Pr1 O7 72.60(12) 2_556 . . yes O5 Pr1 O7 128.89(12) 2_556 . . yes O2 Pr1 N5 80.94(11) 2_556 . 1_655 yes O5 Pr1 N5 147.76(12) 2_556 . 1_655 yes O2 Pr1 O5 86.40(12) 2_556 . 2_556 yes Pr1 O1 C1 132.4(3) . . . yes Pr1 O2 C1 131.1(3) 2_556 . . yes Pr1 O3 C9 101.2(3) . . . yes Pr1 O4 C9 88.3(3) . . . yes Pr1 O5 C17 172.9(3) 2_556 . . yes Pr1 O7 C17 106.1(3) . . . yes C6 N1 C8 106.5(4) . . . yes Pr1 O1W H2W 117(4) . . . no H1W O1W H2W 110(5) . . . no Pr1 O1W H1W 131(3) . . . no C5 N2 C8 103.7(4) . . . yes C14 N3 C16 106.2(4) . . . yes C13 N4 C16 104.0(4) . . . yes Pr1 N5 C24 127.7(3) 1_455 . . yes C22 N5 C24 104.3(4) . . . yes Pr1 N5 C22 127.9(3) 1_455 . . yes C21 N6 C24 107.0(4) . . . yes O1 C1 O2 123.6(4) . . . yes O1 C1 C2 117.1(4) . . . yes C6 N1 H1N 127.00 . . . no C8 N1 H1N 127.00 . . . no O2 C1 C2 119.4(4) . . . yes C1 C2 C3 119.9(4) . . . no C1 C2 C7 119.5(4) . . . no C3 C2 C7 120.6(4) . . . no C16 N3 H3N 127.00 . . . no C14 N3 H3N 127.00 . . . no C2 C3 C4 121.8(5) . . . no C3 C4 C5 117.9(5) . . . no N2 C5 C6 109.9(5) . . . yes N2 C5 C4 130.1(5) . . . yes C4 C5 C6 120.1(5) . . . no N1 C6 C5 105.3(4) . . . yes N1 C6 C7 132.1(5) . . . yes C5 C6 C7 122.7(5) . . . no C21 N6 H6N 126.00 . . . no C24 N6 H6N 127.00 . . . no C2 C7 C6 117.0(5) . . . no N1 C8 N2 114.6(5) . . . yes O3 C9 O4 120.1(4) . . . yes O3 C9 C10 119.1(4) . . . yes O4 C9 C10 120.8(4) . . . yes C9 C10 C11 119.7(5) . . . no C9 C10 C15 120.3(4) . . . no C11 C10 C15 119.9(5) . . . no C10 C11 C12 122.5(5) . . . no C11 C12 C13 118.0(5) . . . no C12 C13 C14 119.7(5) . . . no N4 C13 C14 109.7(5) . . . yes N4 C13 C12 130.6(5) . . . yes N3 C14 C15 131.9(5) . . . yes C13 C14 C15 122.5(5) . . . no N3 C14 C13 105.5(5) . . . yes C10 C15 C14 117.5(4) . . . no N3 C16 N4 114.5(5) . . . yes O5 C17 O7 122.2(4) . . . yes O7 C17 C18 119.4(4) . . . yes O5 C17 C18 118.4(4) . . . yes C17 C18 C19 118.5(4) . . . no C17 C18 C23 120.0(4) . . . no C19 C18 C23 121.3(4) . . . no C18 C19 C20 121.3(4) . . . no C19 C20 C21 117.0(4) . . . no C20 C21 C22 122.5(4) . . . no N6 C21 C22 105.0(4) . . . yes N6 C21 C20 132.5(4) . . . yes N5 C22 C23 130.5(4) . . . yes N5 C22 C21 109.6(4) . . . yes C21 C22 C23 119.9(4) . . . no C18 C23 C22 118.0(4) . . . no N5 C24 N6 114.1(5) . . . 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 121.00 . . . 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 121.00 . . . 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 Pr1 O1 2.434(4) . . yes Pr1 O1W 2.498(4) . . yes Pr1 O3 2.494(4) . . yes Pr1 O4 2.780(4) . . yes Pr1 O7 2.432(4) . . yes Pr1 N5 2.627(4) . 1_655 yes Pr1 O2 2.468(4) . 2_556 yes Pr1 O5 2.429(4) . 2_556 yes Pr1 O5 2.903(3) . . yes O1 C1 1.286(6) . . yes O2 C1 1.245(6) . . yes O3 C9 1.280(6) . . yes O4 C9 1.255(6) . . yes O5 C17 1.289(6) . . yes O7 C17 1.227(6) . . yes N1 C6 1.379(7) . . yes N1 C8 1.338(7) . . yes O1W H1W 0.85(6) . . no O1W H2W 0.85(4) . . no N2 C8 1.323(7) . . yes N2 C5 1.386(6) . . yes N3 C14 1.381(7) . . yes N3 C16 1.352(7) . . yes N4 C16 1.314(7) . . yes N4 C13 1.394(7) . . yes N5 C22 1.401(6) . . yes N5 C24 1.311(7) . . yes N6 C21 1.382(7) . . yes N6 C24 1.352(7) . . yes N1 H1N 0.8600 . . no C1 C2 1.499(7) . . no C2 C7 1.392(7) . . no C2 C3 1.411(7) . . no C3 C4 1.382(8) . . no N3 H3 0.8600 . . no C4 C5 1.387(8) . . no C5 C6 1.406(7) . . no N6 H6N 0.8600 . . no C6 C7 1.383(7) . . no C9 C10 1.499(7) . . no C10 C11 1.416(7) . . no C10 C15 1.386(8) . . no C11 C12 1.372(8) . . no C12 C13 1.393(8) . . no C13 C14 1.404(7) . . no C14 C15 1.393(7) . . no C17 C18 1.501(7) . . no C18 C19 1.415(7) . . no C18 C23 1.375(7) . . no C19 C20 1.374(7) . . no C20 C21 1.384(7) . . no C21 C22 1.406(7) . . no C22 C23 1.393(7) . . 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 2.1000 2.933(7) 163.00 2_767 yes N3 H3N O1 0.8600 2.0500 2.901(6) 168.00 1_655 yes N6 H6N O4 0.8600 1.9800 2.814(6) 164.00 2_566 yes O1W H1W O3 0.85(6) 1.87(6) 2.691(5) 162.00 2_656 yes O1W H2W N2 0.85(4) 2.02(4) 2.848(5) 165.00 1_554 yes C15 H15 O1W 0.9300 2.4500 3.338(6) 161.00 2_656 yes C23 H23 O3 0.9300 2.4400 3.088(6) 126.00 1_455 yes C8 H8 Cg6 0.9300 2.4400 3.186(5) 138.00 1_656 yes C20 H20 Cg2 0.9300 2.5200 3.292(5) 141.00 2_666 yes C20 H20 Cg8 0.9300 2.7200 3.485(5) 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 Pr1 O1 C1 -40.9(5) . . . . no O3 Pr1 O1 C1 -100.5(5) . . . . no O4 Pr1 O1 C1 -149.8(5) . . . . no O7 Pr1 O1 C1 133.6(5) . . . . no N5 Pr1 O1 C1 -164.1(4) 1_655 . . . no O2 Pr1 O1 C1 70.7(5) 2_556 . . . no O5 Pr1 O1 C1 0.5(4) 2_556 . . . no O1 Pr1 O3 C9 -77.7(3) . . . . no O1W Pr1 O3 C9 134.5(3) . . . . no O4 Pr1 O3 C9 -6.9(3) . . . . no O7 Pr1 O3 C9 0.3(3) . . . . no N5 Pr1 O3 C9 63.6(3) 1_655 . . . no O2 Pr1 O3 C9 115.4(3) 2_556 . . . no O5 Pr1 O3 C9 -149.0(3) 2_556 . . . no O1 Pr1 O4 C9 102.7(3) . . . . no O1W Pr1 O4 C9 -36.8(3) . . . . no O3 Pr1 O4 C9 6.9(3) . . . . no O7 Pr1 O4 C9 -167.0(3) . . . . no N5 Pr1 O4 C9 -87.8(3) 1_655 . . . no O2 Pr1 O4 C9 -129.3(3) 2_556 . . . no O5 Pr1 O4 C9 62.8(3) 2_556 . . . no O1 Pr1 O7 C17 -71.2(3) . . . . no O1W Pr1 O7 C17 104.3(3) . . . . no O3 Pr1 O7 C17 -146.9(3) . . . . no O4 Pr1 O7 C17 -141.3(3) . . . . no N5 Pr1 O7 C17 147.8(3) 1_655 . . . no O2 Pr1 O7 C17 62.8(3) 2_556 . . . no O5 Pr1 O7 C17 -7.5(4) 2_556 . . . no O1 Pr1 N5 C22 95.1(4) . . 1_655 1_655 no O1 Pr1 N5 C24 -80.0(4) . . 1_655 1_655 no O1W Pr1 N5 C22 -52.0(4) . . 1_655 1_655 no O1W Pr1 N5 C24 133.0(4) . . 1_655 1_655 no O3 Pr1 N5 C22 31.0(3) . . 1_655 1_655 no O3 Pr1 N5 C24 -144.1(4) . . 1_655 1_655 no O4 Pr1 N5 C22 80.8(4) . . 1_655 1_655 no O4 Pr1 N5 C24 -94.3(4) . . 1_655 1_655 no O7 Pr1 N5 C22 161.2(4) . . 1_655 1_655 no O7 Pr1 N5 C24 -13.9(4) . . 1_655 1_655 no O1 Pr1 O2 C1 -32.5(5) . . 2_556 2_556 no O1W Pr1 O2 C1 110.7(4) . . 2_556 2_556 no O3 Pr1 O2 C1 130.7(4) . . 2_556 2_556 no O4 Pr1 O2 C1 -139.3(4) . . 2_556 2_556 no O7 Pr1 O2 C1 -100.9(4) . . 2_556 2_556 no Pr1 O1 C1 O2 -60.8(7) . . . . no Pr1 O1 C1 C2 119.7(4) . . . . no Pr1 O2 C1 O1 15.7(8) 2_556 . . . no Pr1 O2 C1 C2 -164.7(3) 2_556 . . . no Pr1 O3 C9 O4 13.4(5) . . . . no Pr1 O3 C9 C10 -164.7(3) . . . . no Pr1 O4 C9 O3 -11.8(4) . . . . no Pr1 O4 C9 C10 166.3(4) . . . . no Pr1 O7 C17 O5 15.1(5) . . . . no Pr1 O7 C17 C18 -165.3(3) . . . . no C8 N1 C6 C5 -0.3(6) . . . . no C8 N1 C6 C7 -178.8(6) . . . . no C6 N1 C8 N2 -0.9(6) . . . . no C8 N2 C5 C4 175.6(6) . . . . no C8 N2 C5 C6 -1.8(6) . . . . no C5 N2 C8 N1 1.7(6) . . . . no C16 N3 C14 C13 0.1(5) . . . . no C16 N3 C14 C15 176.7(5) . . . . no C14 N3 C16 N4 0.5(7) . . . . no C16 N4 C13 C12 -178.4(6) . . . . no C16 N4 C13 C14 0.9(6) . . . . no C13 N4 C16 N3 -0.9(6) . . . . no C24 N5 C22 C21 -0.3(5) . . . . no C24 N5 C22 C23 -178.5(5) . . . . no Pr1 N5 C22 C21 -176.3(3) 1_455 . . . no Pr1 N5 C22 C23 5.6(7) 1_455 . . . no C22 N5 C24 N6 0.7(5) . . . . no Pr1 N5 C24 N6 176.7(3) 1_455 . . . no C24 N6 C21 C20 177.3(5) . . . . no C24 N6 C21 C22 0.5(5) . . . . no C21 N6 C24 N5 -0.8(6) . . . . no O1 C1 C2 C3 179.5(5) . . . . no O1 C1 C2 C7 -1.0(7) . . . . no O2 C1 C2 C3 0.0(7) . . . . no O2 C1 C2 C7 179.5(5) . . . . no C1 C2 C3 C4 -177.5(5) . . . . no C7 C2 C3 C4 3.0(8) . . . . no C1 C2 C7 C6 178.9(5) . . . . no C3 C2 C7 C6 -1.6(8) . . . . no C2 C3 C4 C5 -1.7(8) . . . . no C3 C4 C5 N2 -178.1(5) . . . . no C3 C4 C5 C6 -0.9(8) . . . . no N2 C5 C6 N1 1.3(6) . . . . no N2 C5 C6 C7 -180.0(5) . . . . no C4 C5 C6 N1 -176.4(5) . . . . no C4 C5 C6 C7 2.3(8) . . . . no N1 C6 C7 C2 177.3(5) . . . . no C5 C6 C7 C2 -1.0(8) . . . . no O3 C9 C10 C11 -179.1(4) . . . . no O3 C9 C10 C15 4.8(7) . . . . no O4 C9 C10 C11 2.8(7) . . . . no O4 C9 C10 C15 -173.3(4) . . . . no C9 C10 C11 C12 -175.6(5) . . . . no C15 C10 C11 C12 0.5(7) . . . . no C9 C10 C15 C14 175.6(4) . . . . no C11 C10 C15 C14 -0.6(7) . . . . no C10 C11 C12 C13 0.7(8) . . . . no C11 C12 C13 N4 177.5(5) . . . . no C11 C12 C13 C14 -1.8(8) . . . . no N4 C13 C14 N3 -0.6(5) . . . . no N4 C13 C14 C15 -177.6(4) . . . . no C12 C13 C14 N3 178.8(5) . . . . no C12 C13 C14 C15 1.8(7) . . . . no N3 C14 C15 C10 -176.7(5) . . . . no C13 C14 C15 C10 -0.6(7) . . . . no O5 C17 C18 C19 -161.6(4) . . . . no O5 C17 C18 C23 22.5(7) . . . . no O7 C17 C18 C19 18.8(7) . . . . no O7 C17 C18 C23 -157.1(5) . . . . no C17 C18 C19 C20 -176.3(4) . . . . no C23 C18 C19 C20 -0.5(7) . . . . no C17 C18 C23 C22 175.5(4) . . . . no C19 C18 C23 C22 -0.3(7) . . . . no C18 C19 C20 C21 1.5(7) . . . . no C19 C20 C21 N6 -178.1(5) . . . . no C19 C20 C21 C22 -1.8(7) . . . . no N6 C21 C22 N5 -0.2(5) . . . . no N6 C21 C22 C23 178.3(4) . . . . no C20 C21 C22 N5 -177.3(4) . . . . no C20 C21 C22 C23 1.1(7) . . . . no N5 C22 C23 C18 178.0(5) . . . . no C21 C22 C23 C18 0.0(7) . . . . no