#------------------------------------------------------------------------------ #$Date: 2020-08-20 04:47:43 +0300 (Thu, 20 Aug 2020) $ #$Revision: 255465 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705210.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_7705210 loop_ _publ_author_name 'Du, Yi' 'Yang, Huayong' 'Liu, Ruijuan' 'Shao, Caiyun' 'Yang, Li-rong' _publ_section_title ; Multi-responsive Chemosensor for Highly Sensitive and Selective Detection of Fe3+, Cu2+, Cr2O72− and Nitrobenzene based on Luminescent Lanthanide Metal--Organic Framework ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT02120B _journal_year 2020 _chemical_formula_moiety 'C16 H10 O11 Pr, C9 H8 N2' _chemical_formula_sum 'C25 H18 N2 O11 Pr' _chemical_formula_weight 663.32 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2020-08-14 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-08-14 deposited with the CCDC. 2020-08-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 114.725(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.097(5) _cell_length_b 8.503(3) _cell_length_c 19.088(6) _cell_measurement_reflns_used 9897 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.61 _cell_measurement_theta_min 2.67 _cell_volume 2373.1(13) _computing_cell_refinement 'APEX 2' _computing_data_collection 'APEX 2 (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_device_type 'Bruker Smart APEX II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_unetI/netI 0.0474 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.968 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 14902 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.968 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.614 _diffrn_reflns_theta_min 2.173 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.123 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.4698 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1174 before and 0.0567 after correction. The Ratio of minimum to maximum transmission is 0.6300. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.857 _exptl_crystal_description block _exptl_crystal_F_000 1316 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.775 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.099 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 352 _refine_ls_number_reflns 5894 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0254 _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^)+(0.0223P)^2^+1.3097P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.0673 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5426 _reflns_number_total 5894 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02120b2.cif _cod_data_source_block 10671 _cod_original_cell_volume 2373.2(13) _cod_database_code 7705210 _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 0.866 _shelx_estimated_absorpt_t_min 0.515 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups, All O(H,H) groups 2.a Riding coordinates: O1W(H1WA,H1WB), O2W(H2WA,H2WB) 2.b Aromatic/amide H refined with riding coordinates: N2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25) ; _shelx_res_file ; TITL 10671 in P2(1)/c 10671.res created by SHELXL-2018/3 at 17:06:58 on 14-Aug-2020 CELL 0.71073 16.0973 8.5032 19.0879 90 114.7247 90 ZERR 4 0.0052 0.0028 0.0063 0 0.0043 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O Pr UNIT 100 72 8 44 4 EQIV $1 2-X,-Y,2-Z EQIV $2 +X,1+Y,+Z L.S. 64 PLAN 3 SIZE 0.36 0.23 0.07 TEMP 23 HTAB O1W O3_$2 HTAB O1W O6 HTAB O2W O6_$1 HTAB O2W O3 FREE Pr1 C9 BOND $H CONF fmap 2 acta OMIT 0 1 1 OMIT -1 0 4 OMIT -1 2 1 OMIT -1 5 5 OMIT -2 0 14 OMIT 3 0 0 OMIT 6 0 0 OMIT -13 3 2 OMIT 7 0 0 OMIT -5 2 2 OMIT 0 0 2 OMIT 12 2 3 REM REM REM WGHT 0.022300 1.309700 FVAR 0.08832 PR1 5 0.865925 0.088775 0.963156 11.00000 0.01429 0.01461 = 0.01165 -0.00131 0.00467 0.00018 N1 3 0.489964 0.440188 0.738759 11.00000 0.02113 0.04485 = 0.02088 0.00258 0.00681 0.00226 N2 3 0.447911 0.475537 0.617778 11.00000 0.02453 0.04693 = 0.02007 0.00374 0.00418 0.00395 AFIX 43 H2 2 0.415784 0.502143 0.570616 11.00000 -1.20000 AFIX 0 O1 4 0.734723 0.109342 1.183895 11.00000 0.01680 0.01704 = 0.01718 0.00703 0.00202 -0.00089 O2 4 0.773823 -0.125300 0.889211 11.00000 0.01879 0.02063 = 0.02506 -0.00719 0.00671 0.00102 O3 4 0.808047 -0.351167 0.952031 11.00000 0.06137 0.02188 = 0.03215 -0.00395 0.03351 -0.00751 O4 4 0.966626 -0.135281 0.951149 11.00000 0.01692 0.01902 = 0.01617 -0.00595 0.00444 0.00014 O5 4 0.937682 0.189597 1.099005 11.00000 0.01974 0.03344 = 0.02212 -0.00951 0.00930 -0.00683 O6 4 0.909109 0.139804 0.855066 11.00000 0.02383 0.04129 = 0.01773 0.00599 0.00741 0.00689 O7 4 0.765496 0.194888 0.825577 11.00000 0.02697 0.03424 = 0.01797 0.00450 0.01067 0.00781 O8 4 0.732223 0.154398 0.975891 11.00000 0.02106 0.04042 = 0.01927 -0.00676 0.01093 0.00285 O9 4 0.632880 0.094260 1.022508 11.00000 0.03257 0.06359 = 0.02289 -0.01286 0.01528 -0.02049 O1W 4 0.903054 0.381653 0.962403 11.00000 0.04950 0.01993 = 0.03668 0.00558 0.01818 0.00473 AFIX 3 H1WA 2 0.871884 0.458683 0.966763 11.00000 -1.20000 H1WB 2 0.915304 0.406163 0.924593 11.00000 -1.20000 AFIX 0 O2W 4 0.887540 -0.123486 1.062284 11.00000 0.05524 0.02250 = 0.02586 -0.00057 0.02028 -0.00689 AFIX 3 H2WA 2 0.936810 -0.153736 1.099084 11.00000 -1.20000 H2WB 2 0.865020 -0.206586 1.036594 11.00000 -1.20000 AFIX 0 C1 1 0.802689 -0.263610 0.898530 11.00000 0.01935 0.01866 = 0.02474 -0.00738 0.01133 -0.00582 C2 1 0.831847 -0.331907 0.839916 11.00000 0.01992 0.01291 = 0.01600 -0.00046 0.00819 0.00021 C3 1 0.772024 -0.432249 0.785394 11.00000 0.01816 0.01828 = 0.02151 -0.00375 0.00888 -0.00189 AFIX 43 H3 2 0.713336 -0.446404 0.782385 11.00000 -1.20000 AFIX 0 C4 1 0.798693 0.011502 1.235441 11.00000 0.02049 0.01284 = 0.01216 0.00167 0.00371 0.00076 C5 1 0.883774 -0.489931 0.737224 11.00000 0.02667 0.02338 = 0.02093 -0.00792 0.01312 -0.00331 AFIX 43 H5 2 0.901285 -0.543556 0.703111 11.00000 -1.20000 AFIX 0 C6 1 0.942914 -0.387240 0.790538 11.00000 0.02037 0.02440 = 0.02393 -0.00631 0.01180 -0.00428 AFIX 43 H6 2 1.000719 -0.370835 0.791959 11.00000 -1.20000 AFIX 0 C7 1 0.917806 -0.307580 0.842310 11.00000 0.01734 0.01444 = 0.01537 -0.00105 0.00581 -0.00009 C8 1 0.985896 -0.203618 0.900517 11.00000 0.01741 0.01367 = 0.01559 0.00042 0.00396 -0.00027 C9 1 0.828550 0.164375 0.806077 11.00000 0.02778 0.01771 = 0.01754 0.00362 0.00988 0.00382 C10 1 0.809192 0.357743 1.223234 11.00000 0.02544 0.01987 = 0.01556 -0.00057 0.01011 -0.00081 C11 1 0.835930 0.498803 1.203252 11.00000 0.04476 0.02021 = 0.02825 -0.00534 0.02012 -0.00810 AFIX 43 H11 2 0.866731 0.572357 1.241383 11.00000 -1.20000 AFIX 0 C12 1 0.817563 0.531916 1.127591 11.00000 0.04730 0.02229 = 0.03353 0.00455 0.02149 -0.00521 AFIX 43 H12 2 0.833949 0.628572 1.114337 11.00000 -1.20000 AFIX 0 C13 1 0.775120 0.421585 1.072323 11.00000 0.03514 0.02518 = 0.02087 0.00670 0.01697 0.00316 AFIX 43 H13 2 0.764858 0.442600 1.021539 11.00000 -1.20000 AFIX 0 C14 1 0.747050 0.279761 1.089800 11.00000 0.01809 0.02165 = 0.01430 0.00191 0.00810 0.00366 C15 1 0.764379 0.249092 1.166042 11.00000 0.01662 0.01503 = 0.01570 0.00298 0.00716 0.00140 C16 1 0.700268 0.165929 1.025922 11.00000 0.01977 0.02793 = 0.01290 0.00039 0.00489 0.00407 C17 1 0.421660 0.405561 0.828367 11.00000 0.04472 0.14498 = 0.04006 -0.03809 0.02589 -0.04037 AFIX 43 H17 2 0.370765 0.360164 0.789323 11.00000 -1.20000 AFIX 0 C18 1 0.425121 0.423882 0.901601 11.00000 0.05918 0.15851 = 0.05107 -0.04724 0.04249 -0.05297 AFIX 43 H18 2 0.375706 0.390184 0.910923 11.00000 -1.20000 AFIX 0 C19 1 0.498374 0.489554 0.960539 11.00000 0.03116 0.06243 = 0.02744 -0.00070 0.01462 0.00390 C20 1 0.568032 0.542102 0.943695 11.00000 0.02981 0.07843 = 0.02238 0.00261 0.00642 -0.00636 AFIX 43 H20 2 0.617983 0.591455 0.981963 11.00000 -1.20000 AFIX 0 C21 1 0.566079 0.523760 0.871409 11.00000 0.03229 0.07868 = 0.02584 0.00137 0.01168 -0.00898 AFIX 43 H21 2 0.614864 0.558921 0.861562 11.00000 -1.20000 AFIX 0 C22 1 0.492896 0.454271 0.814312 11.00000 0.02623 0.04848 = 0.02244 0.00050 0.00987 0.00431 C23 1 0.558383 0.383146 0.720619 11.00000 0.02098 0.03860 = 0.02466 0.00350 0.00705 0.00416 AFIX 43 H23 2 0.612879 0.337241 0.754435 11.00000 -1.20000 AFIX 0 C24 1 0.531471 0.406391 0.644761 11.00000 0.02287 0.04548 = 0.02646 0.00133 0.00863 0.00416 AFIX 43 H24 2 0.563991 0.380050 0.616038 11.00000 -1.20000 AFIX 0 C25 1 0.423898 0.495373 0.674557 11.00000 0.02142 0.04994 = 0.02694 0.00295 0.00616 0.00478 AFIX 43 H25 2 0.369552 0.540632 0.670693 11.00000 -1.20000 AFIX 0 HKLF 4 REM 10671 in P2(1)/c REM wR2 = 0.0673, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0254 for 5426 Fo > 4sig(Fo) and 0.0279 for all 5894 data REM 352 parameters refined using 0 restraints END WGHT 0.0223 1.3098 REM Highest difference peak 0.775, deepest hole -0.723, 1-sigma level 0.099 Q1 1 0.7856 -0.0318 0.9185 11.00000 0.05 0.78 Q2 1 1.0497 -0.2202 0.9866 11.00000 0.05 0.70 Q3 1 0.9410 -0.0217 1.0010 11.00000 0.05 0.70 ; _shelx_res_checksum 72972 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0.86592(2) 0.08878(2) 0.96316(2) 0.01377(5) Uani 1 1 d . . . . . N1 N 0.48996(15) 0.4402(3) 0.73876(12) 0.0296(5) Uani 1 1 d . . . . . N2 N 0.44791(15) 0.4755(3) 0.61778(12) 0.0323(5) Uani 1 1 d . . . . . H2 H 0.415784 0.502143 0.570616 0.039 Uiso 1 1 calc R . . . . O1 O 0.73472(11) 0.10934(17) 1.18389(9) 0.0187(3) Uani 1 1 d . . . . . O2 O 0.77382(11) -0.12530(19) 0.88921(9) 0.0223(3) Uani 1 1 d . . . . . O3 O 0.80805(14) -0.3512(2) 0.95203(10) 0.0338(4) Uani 1 1 d . . . . . O4 O 0.96663(10) -0.13528(18) 0.95115(8) 0.0182(3) Uani 1 1 d . . . . . O5 O 0.93768(11) 0.1896(2) 1.09901(9) 0.0249(4) Uani 1 1 d . . . . . O6 O 0.90911(12) 0.1398(2) 0.85507(9) 0.0281(4) Uani 1 1 d . . . . . O7 O 0.76550(12) 0.1949(2) 0.82558(9) 0.0260(4) Uani 1 1 d . . . . . O8 O 0.73222(11) 0.1544(2) 0.97589(9) 0.0261(4) Uani 1 1 d . . . . . O9 O 0.63288(14) 0.0943(3) 1.02251(12) 0.0384(6) Uani 1 1 d . . . . . O1W O 0.90305(15) 0.3817(2) 0.96240(11) 0.0353(4) Uani 1 1 d . . . . . H1WA H 0.871884 0.458683 0.966763 0.042 Uiso 1 1 d R . . . . H1WB H 0.915304 0.406163 0.924593 0.042 Uiso 1 1 d R . . . . O2W O 0.88754(15) -0.1235(2) 1.06228(11) 0.0334(4) Uani 1 1 d . . . . . H2WA H 0.936810 -0.153736 1.099084 0.040 Uiso 1 1 d R . . . . H2WB H 0.865020 -0.206586 1.036594 0.040 Uiso 1 1 d R . . . . C1 C 0.80269(15) -0.2636(3) 0.89853(13) 0.0202(4) Uani 1 1 d . . . . . C2 C 0.83185(15) -0.3319(2) 0.83992(12) 0.0160(4) Uani 1 1 d . . . . . C3 C 0.77202(16) -0.4322(3) 0.78539(13) 0.0191(4) Uani 1 1 d . . . . . H3 H 0.713336 -0.446404 0.782385 0.023 Uiso 1 1 calc R . . . . C4 C 0.79869(15) 0.0115(2) 1.23544(11) 0.0162(4) Uani 1 1 d . . . . . C5 C 0.88377(16) -0.4899(3) 0.73722(13) 0.0226(5) Uani 1 1 d . . . . . H5 H 0.901285 -0.543556 0.703111 0.027 Uiso 1 1 calc R . . . . C6 C 0.94291(17) -0.3872(3) 0.79054(14) 0.0220(5) Uani 1 1 d . . . . . H6 H 1.000719 -0.370835 0.791959 0.026 Uiso 1 1 calc R . . . . C7 C 0.91781(15) -0.3076(2) 0.84231(12) 0.0161(4) Uani 1 1 d . . . . . C8 C 0.98590(15) -0.2036(2) 0.90052(12) 0.0166(4) Uani 1 1 d . . . . . C9 C 0.82855(16) 0.1644(3) 0.80608(12) 0.0209(4) Uani 1 1 d . . . . . C10 C 0.80919(16) 0.3577(3) 1.22323(12) 0.0198(4) Uani 1 1 d . . . . . C11 C 0.8359(2) 0.4988(3) 1.20325(15) 0.0294(5) Uani 1 1 d . . . . . H11 H 0.866731 0.572357 1.241383 0.035 Uiso 1 1 calc R . . . . C12 C 0.8176(2) 0.5319(3) 1.12759(15) 0.0328(6) Uani 1 1 d . . . . . H12 H 0.833949 0.628572 1.114337 0.039 Uiso 1 1 calc R . . . . C13 C 0.77512(19) 0.4216(3) 1.07232(14) 0.0253(5) Uani 1 1 d . . . . . H13 H 0.764858 0.442600 1.021539 0.030 Uiso 1 1 calc R . . . . C14 C 0.74705(15) 0.2798(3) 1.08980(12) 0.0176(4) Uani 1 1 d . . . . . C15 C 0.76438(14) 0.2491(2) 1.16604(11) 0.0156(4) Uani 1 1 d . . . . . C16 C 0.70027(15) 0.1659(3) 1.02592(12) 0.0209(4) Uani 1 1 d . . . . . C17 C 0.4217(3) 0.4056(6) 0.8284(2) 0.0738(16) Uani 1 1 d . . . . . H17 H 0.370765 0.360164 0.789323 0.089 Uiso 1 1 calc R . . . . C18 C 0.4251(3) 0.4239(6) 0.9016(2) 0.0830(18) Uani 1 1 d . . . . . H18 H 0.375706 0.390184 0.910923 0.100 Uiso 1 1 calc R . . . . C19 C 0.4984(2) 0.4896(4) 0.96054(15) 0.0395(7) Uani 1 1 d . . . . . C20 C 0.5680(2) 0.5421(4) 0.94370(16) 0.0451(7) Uani 1 1 d . . . . . H20 H 0.617983 0.591455 0.981963 0.054 Uiso 1 1 calc R . . . . C21 C 0.5661(2) 0.5238(5) 0.87141(16) 0.0458(8) Uani 1 1 d . . . . . H21 H 0.614864 0.558921 0.861562 0.055 Uiso 1 1 calc R . . . . C22 C 0.49290(18) 0.4543(4) 0.81431(14) 0.0325(6) Uani 1 1 d . . . . . C23 C 0.55838(18) 0.3831(3) 0.72062(15) 0.0289(5) Uani 1 1 d . . . . . H23 H 0.612879 0.337241 0.754435 0.035 Uiso 1 1 calc R . . . . C24 C 0.53147(19) 0.4064(3) 0.64476(16) 0.0322(6) Uani 1 1 d . . . . . H24 H 0.563991 0.380050 0.616038 0.039 Uiso 1 1 calc R . . . . C25 C 0.42390(18) 0.4954(4) 0.67456(15) 0.0341(6) Uani 1 1 d . . . . . H25 H 0.369552 0.540632 0.670693 0.041 Uiso 1 1 calc R . . . . 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 0.01429(8) 0.01461(7) 0.01165(7) -0.00131(3) 0.00467(5) 0.00018(4) N1 0.0211(11) 0.0449(13) 0.0209(10) 0.0026(9) 0.0068(9) 0.0023(9) N2 0.0245(11) 0.0469(14) 0.0201(10) 0.0037(9) 0.0042(8) 0.0040(10) O1 0.0168(8) 0.0170(7) 0.0172(7) 0.0070(6) 0.0020(6) -0.0009(6) O2 0.0188(8) 0.0206(8) 0.0251(8) -0.0072(6) 0.0067(7) 0.0010(6) O3 0.0614(13) 0.0219(9) 0.0322(9) -0.0040(7) 0.0335(10) -0.0075(8) O4 0.0169(8) 0.0190(7) 0.0162(7) -0.0059(6) 0.0044(6) 0.0001(6) O5 0.0197(8) 0.0334(9) 0.0221(8) -0.0095(7) 0.0093(7) -0.0068(7) O6 0.0238(9) 0.0413(10) 0.0177(8) 0.0060(7) 0.0074(7) 0.0069(8) O7 0.0270(9) 0.0342(10) 0.0180(7) 0.0045(7) 0.0107(7) 0.0078(7) O8 0.0211(8) 0.0404(10) 0.0193(8) -0.0068(7) 0.0109(7) 0.0029(7) O9 0.0326(12) 0.0636(16) 0.0229(9) -0.0129(8) 0.0153(9) -0.0205(9) O1W 0.0495(13) 0.0199(9) 0.0367(11) 0.0056(7) 0.0182(10) 0.0047(8) O2W 0.0552(13) 0.0225(9) 0.0259(9) -0.0006(7) 0.0203(9) -0.0069(8) C1 0.0194(11) 0.0187(10) 0.0247(11) -0.0074(8) 0.0113(9) -0.0058(8) C2 0.0199(11) 0.0129(9) 0.0160(9) -0.0005(7) 0.0082(8) 0.0002(7) C3 0.0182(11) 0.0183(10) 0.0215(11) -0.0038(8) 0.0089(9) -0.0019(8) C4 0.0205(10) 0.0128(9) 0.0122(9) 0.0017(7) 0.0037(8) 0.0008(8) C5 0.0267(12) 0.0234(11) 0.0209(10) -0.0079(9) 0.0131(9) -0.0033(9) C6 0.0204(12) 0.0244(11) 0.0239(11) -0.0063(9) 0.0118(10) -0.0043(9) C7 0.0173(10) 0.0144(9) 0.0154(9) -0.0010(7) 0.0058(8) -0.0001(7) C8 0.0174(10) 0.0137(9) 0.0156(9) 0.0004(7) 0.0040(8) -0.0003(7) C9 0.0278(12) 0.0177(10) 0.0175(10) 0.0036(8) 0.0099(9) 0.0038(8) C10 0.0254(12) 0.0199(11) 0.0156(10) -0.0006(8) 0.0101(9) -0.0008(9) C11 0.0448(15) 0.0202(11) 0.0282(12) -0.0053(9) 0.0201(12) -0.0081(10) C12 0.0473(17) 0.0223(12) 0.0335(13) 0.0045(10) 0.0215(13) -0.0052(11) C13 0.0351(14) 0.0252(12) 0.0209(11) 0.0067(8) 0.0170(11) 0.0032(9) C14 0.0181(10) 0.0216(10) 0.0143(9) 0.0019(8) 0.0081(8) 0.0037(8) C15 0.0166(10) 0.0150(9) 0.0157(9) 0.0030(7) 0.0072(8) 0.0014(7) C16 0.0198(11) 0.0279(12) 0.0129(9) 0.0004(8) 0.0049(8) 0.0041(9) C17 0.045(2) 0.145(5) 0.0401(19) -0.038(2) 0.0259(18) -0.040(2) C18 0.059(3) 0.159(5) 0.051(2) -0.047(3) 0.042(2) -0.053(3) C19 0.0312(15) 0.062(2) 0.0274(14) -0.0007(13) 0.0146(12) 0.0039(13) C20 0.0298(15) 0.078(2) 0.0224(13) 0.0026(14) 0.0064(12) -0.0064(15) C21 0.0323(16) 0.079(2) 0.0258(13) 0.0014(14) 0.0117(12) -0.0090(15) C22 0.0262(13) 0.0485(16) 0.0224(12) 0.0005(11) 0.0099(11) 0.0043(11) C23 0.0210(13) 0.0386(14) 0.0247(12) 0.0035(10) 0.0071(10) 0.0042(10) C24 0.0229(13) 0.0455(17) 0.0265(13) 0.0013(10) 0.0086(11) 0.0042(10) C25 0.0214(12) 0.0499(17) 0.0269(12) 0.0029(11) 0.0062(10) 0.0048(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pr Pr -0.2180 2.8214 '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 O2 Pr1 O4 69.09(6) . . ? O2 Pr1 O4 136.70(5) . 3_757 ? O2 Pr1 O5 140.53(6) . . ? O2 Pr1 O6 87.85(6) . . ? O2 Pr1 O7 72.49(6) . . ? O2 Pr1 O1W 145.33(6) . . ? O2 Pr1 O2W 75.91(6) . . ? O2 Pr1 C8 150.14(6) . 3_757 ? O4 Pr1 O4 68.47(6) 3_757 . ? O4 Pr1 O7 129.94(5) 3_757 . ? O4 Pr1 O7 108.39(5) . . ? O4 Pr1 O1W 70.37(6) 3_757 . ? O4 Pr1 C8 26.33(5) 3_757 3_757 ? O4 Pr1 C8 90.98(6) . 3_757 ? O5 Pr1 O4 51.17(5) . 3_757 ? O5 Pr1 O4 108.08(5) . . ? O5 Pr1 O7 138.42(6) . . ? O5 Pr1 O1W 70.48(6) . . ? O5 Pr1 O2W 67.11(6) . . ? O5 Pr1 C8 25.39(6) . 3_757 ? O6 Pr1 O4 85.23(6) . 3_757 ? O6 Pr1 O4 69.42(6) . . ? O6 Pr1 O5 129.31(6) . . ? O6 Pr1 O7 51.00(6) . . ? O6 Pr1 O1W 71.19(6) . . ? O6 Pr1 O2W 138.52(6) . . ? O6 Pr1 C8 106.24(7) . 3_757 ? O7 Pr1 C8 136.68(6) . 3_757 ? O8 Pr1 O2 82.69(6) . . ? O8 Pr1 O4 146.06(6) . . ? O8 Pr1 O4 132.44(6) . 3_757 ? O8 Pr1 O5 81.75(6) . . ? O8 Pr1 O6 129.64(6) . . ? O8 Pr1 O7 79.13(6) . . ? O8 Pr1 O1W 89.75(7) . . ? O8 Pr1 O2W 86.39(7) . . ? O8 Pr1 C8 106.11(6) . 3_757 ? O1W Pr1 O4 124.19(6) . . ? O1W Pr1 O7 72.86(6) . . ? O1W Pr1 C8 64.32(6) . 3_757 ? O2W Pr1 O4 69.14(6) . . ? O2W Pr1 O4 81.49(6) . 3_757 ? O2W Pr1 O7 146.58(6) . . ? O2W Pr1 O1W 137.53(6) . . ? O2W Pr1 C8 76.26(7) . 3_757 ? C23 N1 C22 126.4(2) . . ? C25 N1 C22 125.3(2) . . ? C25 N1 C23 108.0(2) . . ? C24 N2 H2 125.3 . . ? C25 N2 H2 125.3 . . ? C25 N2 C24 109.4(2) . . ? C4 O1 C15 117.94(17) . . ? C1 O2 Pr1 121.94(14) . . ? Pr1 O4 Pr1 111.53(6) 3_757 . ? C8 O4 Pr1 91.73(13) . 3_757 ? C8 O4 Pr1 140.24(13) . . ? C8 O5 Pr1 93.86(13) 3_757 . ? C9 O6 Pr1 94.99(14) . . ? C9 O7 Pr1 89.39(13) . . ? C16 O8 Pr1 141.47(15) . . ? Pr1 O1W H1WA 126.8 . . ? Pr1 O1W H1WB 112.4 . . ? H1WA O1W H1WB 104.5 . . ? Pr1 O2W H2WA 128.5 . . ? Pr1 O2W H2WB 105.6 . . ? H2WA O2W H2WB 104.5 . . ? O2 C1 C2 118.2(2) . . ? O3 C1 O2 125.3(2) . . ? O3 C1 C2 116.6(2) . . ? C3 C2 C1 117.72(19) . . ? C3 C2 C7 119.45(19) . . ? C7 C2 C1 122.64(19) . . ? C2 C3 H3 119.8 . . ? C4 C3 C2 120.3(2) 4 . ? C4 C3 H3 119.8 4 . ? O1 C4 C3 115.9(2) . 4_556 ? C5 C4 O1 122.94(19) 4_556 . ? C5 C4 C3 121.1(2) 4_556 4_556 ? C4 C5 H5 120.7 4 . ? C4 C5 C6 118.6(2) 4 . ? C6 C5 H5 120.7 . . ? C5 C6 H6 119.4 . . ? C5 C6 C7 121.2(2) . . ? C7 C6 H6 119.4 . . ? C2 C7 C6 119.3(2) . . ? C2 C7 C8 122.04(19) . . ? C6 C7 C8 118.7(2) . . ? O4 C8 Pr1 61.94(11) . 3_757 ? O4 C8 C7 120.19(19) . . ? O5 C8 Pr1 60.75(11) 3_757 3_757 ? O5 C8 O4 120.66(19) 3_757 . ? O5 C8 C7 119.08(19) 3_757 . ? C7 C8 Pr1 163.07(14) . 3_757 ? O6 C9 C10 117.4(2) . 4_565 ? O7 C9 O6 121.8(2) . . ? O7 C9 C10 120.6(2) . 4_565 ? C11 C10 C9 116.9(2) . 4_566 ? C11 C10 C15 118.9(2) . . ? C15 C10 C9 124.2(2) . 4_566 ? C10 C11 H11 119.6 . . ? C12 C11 C10 120.8(2) . . ? C12 C11 H11 119.6 . . ? C11 C12 H12 120.3 . . ? C13 C12 C11 119.3(2) . . ? C13 C12 H12 120.3 . . ? C12 C13 H13 119.2 . . ? C12 C13 C14 121.6(2) . . ? C14 C13 H13 119.2 . . ? C13 C14 C15 118.5(2) . . ? C13 C14 C16 118.37(19) . . ? C15 C14 C16 123.2(2) . . ? O1 C15 C10 120.18(18) . . ? O1 C15 C14 118.95(19) . . ? C10 C15 C14 120.9(2) . . ? O8 C16 C14 116.3(2) . . ? O9 C16 O8 123.6(2) . . ? O9 C16 C14 120.1(2) . . ? C18 C17 H17 120.4 . . ? C22 C17 H17 120.4 . . ? C22 C17 C18 119.2(3) . . ? C17 C18 H18 118.8 . . ? C19 C18 C17 122.3(3) . . ? C19 C18 H18 118.8 . . ? C18 C19 C19 122.3(4) . 3_667 ? C18 C19 C20 116.9(3) . . ? C20 C19 C19 120.8(3) . 3_667 ? C19 C20 H20 119.2 . . ? C19 C20 C21 121.5(3) . . ? C21 C20 H20 119.2 . . ? C20 C21 H21 119.9 . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 119.9 . . ? C17 C22 N1 120.3(3) . . ? C17 C22 C21 119.9(3) . . ? C21 C22 N1 119.8(3) . . ? N1 C23 H23 126.6 . . ? C24 C23 N1 106.8(2) . . ? C24 C23 H23 126.6 . . ? N2 C24 H24 126.4 . . ? C23 C24 N2 107.2(2) . . ? C23 C24 H24 126.4 . . ? N1 C25 H25 125.7 . . ? N2 C25 N1 108.6(2) . . ? N2 C25 H25 125.7 . . ? 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 Pr1 O2 2.3986(17) . ? Pr1 O4 2.5731(16) . ? Pr1 O4 2.5317(17) 3_757 ? Pr1 O5 2.5075(17) . ? Pr1 O6 2.4755(18) . ? Pr1 O7 2.6024(18) . ? Pr1 O8 2.3324(17) . ? Pr1 O1W 2.563(2) . ? Pr1 O2W 2.5314(19) . ? Pr1 C8 2.867(2) 3_757 ? N1 C22 1.428(3) . ? N1 C23 1.374(3) . ? N1 C25 1.328(3) . ? N2 H2 0.8600 . ? N2 C24 1.357(4) . ? N2 C25 1.305(3) . ? O1 C4 1.369(2) . ? O1 C15 1.376(2) . ? O2 C1 1.250(3) . ? O3 C1 1.237(3) . ? O4 C8 1.272(2) . ? O5 C8 1.232(3) 3_757 ? O6 C9 1.259(3) . ? O7 C9 1.246(3) . ? O8 C16 1.264(3) . ? O9 C16 1.222(3) . ? O1W H1WA 0.8501 . ? O1W H1WB 0.8498 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? C1 C2 1.500(3) . ? C2 C3 1.378(3) . ? C2 C7 1.381(3) . ? C3 H3 0.9300 . ? C3 C4 1.375(3) 4 ? C4 C5 1.368(3) 4_556 ? C5 H5 0.9300 . ? C5 C6 1.376(3) . ? C6 H6 0.9300 . ? C6 C7 1.390(3) . ? C7 C8 1.483(3) . ? C9 C10 1.490(3) 4_565 ? C10 C11 1.381(3) . ? C10 C15 1.381(3) . ? C11 H11 0.9300 . ? C11 C12 1.377(3) . ? C12 H12 0.9300 . ? C12 C13 1.363(4) . ? C13 H13 0.9300 . ? C13 C14 1.377(3) . ? C14 C15 1.387(3) . ? C14 C16 1.491(3) . ? C17 H17 0.9300 . ? C17 C18 1.384(5) . ? C17 C22 1.348(5) . ? C18 H18 0.9300 . ? C18 C19 1.363(5) . ? C19 C19 1.496(5) 3_667 ? C19 C20 1.365(4) . ? C20 H20 0.9300 . ? C20 C21 1.376(4) . ? C21 H21 0.9300 . ? C21 C22 1.360(4) . ? C23 H23 0.9300 . ? C23 C24 1.341(4) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? 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 O1W H1WA O3 0.85 1.87 2.699(3) 163.7 1_565 yes O1W H1WB O6 0.85 2.61 2.933(3) 104.3 . yes O2W H2WA O6 0.85 2.26 2.984(3) 142.8 3_757 yes O2W H2WB O3 0.85 1.93 2.750(3) 162.1 . 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 Pr1 O2 C1 O3 77.8(3) . . . . ? Pr1 O2 C1 C2 -103.4(2) . . . . ? Pr1 O4 C8 Pr1 127.6(2) . . . 3_757 ? Pr1 O4 C8 O5 111.3(2) . . . 3_757 ? Pr1 O4 C8 O5 -16.3(2) 3_757 . . 3_757 ? Pr1 O4 C8 C7 160.75(17) 3_757 . . . ? Pr1 O4 C8 C7 -71.6(3) . . . . ? Pr1 O6 C9 O7 17.7(2) . . . . ? Pr1 O6 C9 C10 -157.19(18) . . . 4_565 ? Pr1 O7 C9 O6 -16.8(2) . . . . ? Pr1 O7 C9 C10 157.99(19) . . . 4_565 ? Pr1 O8 C16 O9 -122.6(3) . . . . ? Pr1 O8 C16 C14 60.2(3) . . . . ? N1 C23 C24 N2 -0.3(3) . . . . ? O2 C1 C2 C3 -101.4(2) . . . . ? O2 C1 C2 C7 83.6(3) . . . . ? O3 C1 C2 C3 77.5(3) . . . . ? O3 C1 C2 C7 -97.5(3) . . . . ? C1 C2 C3 C4 -173.0(2) . . . 4 ? C1 C2 C7 C6 173.7(2) . . . . ? C1 C2 C7 C8 -3.9(3) . . . . ? C2 C7 C8 Pr1 93.5(5) . . . 3_757 ? C2 C7 C8 O4 1.1(3) . . . . ? C2 C7 C8 O5 178.2(2) . . . 3_757 ? C3 C2 C7 C6 -1.2(3) . . . . ? C3 C2 C7 C8 -178.8(2) . . . . ? C4 O1 C15 C10 -59.8(3) . . . . ? C4 O1 C15 C14 121.4(2) . . . . ? C4 C5 C6 C7 0.6(4) 4 . . . ? C5 C6 C7 C2 -0.2(3) . . . . ? C5 C6 C7 C8 177.5(2) . . . . ? C6 C7 C8 Pr1 -84.0(5) . . . 3_757 ? C6 C7 C8 O4 -176.5(2) . . . . ? C6 C7 C8 O5 0.6(3) . . . 3_757 ? C7 C2 C3 C4 2.1(3) . . . 4 ? C9 C10 C11 C12 -177.4(3) 4_566 . . . ? C9 C10 C15 O1 -0.3(3) 4_566 . . . ? C9 C10 C15 C14 178.5(2) 4_566 . . . ? C10 C11 C12 C13 -2.2(4) . . . . ? C11 C10 C15 O1 -178.2(2) . . . . ? C11 C10 C15 C14 0.6(3) . . . . ? C11 C12 C13 C14 2.4(4) . . . . ? C12 C13 C14 C15 -1.2(4) . . . . ? C12 C13 C14 C16 179.4(2) . . . . ? C13 C14 C15 O1 178.5(2) . . . . ? C13 C14 C15 C10 -0.4(3) . . . . ? C13 C14 C16 O8 40.1(3) . . . . ? C13 C14 C16 O9 -137.3(3) . . . . ? C15 O1 C4 C3 142.7(2) . . . 4_556 ? C15 O1 C4 C5 -38.5(3) . . . 4_556 ? C15 C10 C11 C12 0.7(4) . . . . ? C15 C14 C16 O8 -139.3(2) . . . . ? C15 C14 C16 O9 43.3(3) . . . . ? C16 C14 C15 O1 -2.1(3) . . . . ? C16 C14 C15 C10 179.0(2) . . . . ? C17 C18 C19 C19 179.5(5) . . . 3_667 ? C17 C18 C19 C20 2.1(7) . . . . ? C18 C17 C22 N1 -178.4(4) . . . . ? C18 C17 C22 C21 -1.5(7) . . . . ? C18 C19 C20 C21 -2.6(6) . . . . ? C19 C19 C20 C21 180.0(4) 3_667 . . . ? C19 C20 C21 C22 1.1(6) . . . . ? C20 C21 C22 N1 178.0(3) . . . . ? C20 C21 C22 C17 1.0(6) . . . . ? C22 N1 C23 C24 -173.4(3) . . . . ? C22 N1 C25 N2 173.7(3) . . . . ? C22 C17 C18 C19 -0.1(8) . . . . ? C23 N1 C22 C17 -133.8(4) . . . . ? C23 N1 C22 C21 49.2(4) . . . . ? C23 N1 C25 N2 0.0(3) . . . . ? C24 N2 C25 N1 -0.2(3) . . . . ? C25 N1 C22 C17 53.6(5) . . . . ? C25 N1 C22 C21 -123.4(3) . . . . ? C25 N1 C23 C24 0.2(3) . . . . ? C25 N2 C24 C23 0.3(3) . . . . ?