#------------------------------------------------------------------------------ #$Date: 2020-08-20 04:47:43 +0300 (Thu, 20 Aug 2020) $ #$Revision: 255465 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705213.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_7705213 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 Ce O11, C9 H8 N2' _chemical_formula_sum 'C25 H18 Ce N2 O11' _chemical_formula_weight 662.53 _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 114.7250(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.2883(10) _cell_length_b 8.5827(5) _cell_length_c 19.2359(12) _cell_measurement_reflns_used 5800 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.27 _cell_measurement_theta_min 2.33 _cell_volume 2442.6(3) _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 0.998 _diffrn_measured_fraction_theta_max 0.981 _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 0.0342 _diffrn_reflns_av_unetI/netI 0.0462 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 15164 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.326 _diffrn_reflns_theta_min 2.155 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.932 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0838 before and 0.0440 after correction. The Ratio of minimum to maximum transmission is 0.8381. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.802 _exptl_crystal_description block _exptl_crystal_F_000 1312 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.505 _refine_diff_density_min -0.622 _refine_diff_density_rms 0.100 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 352 _refine_ls_number_reflns 5972 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0280 _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^)+(0.0204P)^2^+1.5007P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.0637 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4941 _reflns_number_total 5972 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02120b2.cif _cod_data_source_block 10723 _cod_database_code 7705213 _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 0.877 _shelx_estimated_absorpt_t_min 0.512 _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: N1(H1), C1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C14(H14), C15(H15), C20(H20), C21(H21), C22(H22) ; _shelx_res_file ; TITL 10723 in P2(1)/c 10723.res created by SHELXL-2018/3 at 17:04:21 on 14-Aug-2020 CELL 0.71073 16.2883 8.5827 19.2359 90 114.725 90 ZERR 4 0.001 0.0005 0.0012 0 0.0009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Ce N O UNIT 100 72 4 8 44 EQIV $1 -X,2-Y,1-Z EQIV $2 +X,1+Y,+Z EQIV $3 1-X,-0.5+Y,1.5-Z EQIV $4 -X,-0.5+Y,1.5-Z L.S. 20 PLAN 5 SIZE 0.4 0.22 0.07 TEMP 23 HTAB C14 O4_$4 HTAB C3 O6_$3 HTAB C2 O8_$3 HTAB C2 O5_$3 HTAB C1 O6 HTAB C1 O1 HTAB O2W O7 HTAB O2W O6 HTAB O2W O2_$2 HTAB O1W O7_$1 HTAB O1W O2 FREE Ce1 C18 BOND $H CONF fmap 2 acta OMIT 1 0 0 OMIT -11 7 19 OMIT 2 2 5 OMIT -6 11 3 REM REM REM WGHT 0.020400 1.500700 FVAR 0.08163 CE1 3 0.134455 1.089355 0.537013 11.00000 0.01664 0.01683 = 0.01336 0.00141 0.00581 -0.00025 N1 4 0.448558 0.976379 0.618185 11.00000 0.02753 0.04989 = 0.02282 0.00572 0.00616 0.00312 AFIX 43 H1 2 0.417062 1.003063 0.571390 11.00000 -1.20000 AFIX 0 N2 4 0.490162 0.940790 0.739190 11.00000 0.02370 0.04619 = 0.02368 0.00228 0.00791 0.00224 O1 5 0.226781 0.873995 0.611657 11.00000 0.01973 0.02404 = 0.02976 0.00964 0.00812 -0.00040 O2 5 0.191996 0.648769 0.548699 11.00000 0.06469 0.02538 = 0.03671 0.00503 0.03572 0.00732 O3 5 0.034003 0.864820 0.549648 11.00000 0.01913 0.02175 = 0.01995 0.00614 0.00763 -0.00008 O4 5 -0.061684 0.810779 0.600051 11.00000 0.02269 0.03529 = 0.02378 0.00927 0.01225 0.00730 O5 5 0.265573 1.391169 0.816632 11.00000 0.02023 0.01930 = 0.01857 0.00753 0.00399 -0.00066 O6 5 0.234368 1.195854 0.675168 11.00000 0.03010 0.03711 = 0.01936 -0.00432 0.01068 -0.00940 O7 5 0.091034 1.141863 0.645661 11.00000 0.02817 0.04402 = 0.02107 -0.00726 0.01061 -0.00621 O8 5 0.368396 1.405051 0.977937 11.00000 0.03824 0.06464 = 0.02447 -0.01341 0.01668 -0.02276 O9 5 0.269339 1.345402 1.024788 11.00000 0.02573 0.04493 = 0.02027 -0.00730 0.01286 0.00278 O1W 5 0.112676 0.874490 0.437354 11.00000 0.05995 0.02978 = 0.03131 0.00120 0.02374 0.00759 AFIX 3 H1WA 2 0.131296 0.793040 0.464644 11.00000 -1.20000 H1WB 2 0.055466 0.865320 0.416744 11.00000 -1.20000 AFIX 0 O2W 5 0.096164 1.383708 0.536923 11.00000 0.05732 0.02299 = 0.03507 -0.00251 0.01678 0.00058 AFIX 3 H2WA 2 0.079404 1.477448 0.524863 11.00000 -1.20000 H2WB 2 0.103904 1.375938 0.583313 11.00000 -1.20000 AFIX 0 C1 1 0.424519 0.995425 0.674798 11.00000 0.02430 0.05002 = 0.03054 0.00491 0.00870 0.00743 AFIX 43 H1A 2 0.370609 1.039708 0.670796 11.00000 -1.20000 AFIX 0 C2 1 0.531760 0.907263 0.645641 11.00000 0.02677 0.04639 = 0.03003 -0.00019 0.01312 0.00216 AFIX 43 H2 2 0.564144 0.881430 0.617308 11.00000 -1.20000 AFIX 0 C3 1 0.558223 0.883460 0.720866 11.00000 0.02053 0.04347 = 0.02823 0.00299 0.00810 0.00360 AFIX 43 H3 2 0.611925 0.837345 0.754310 11.00000 -1.20000 AFIX 0 C4 1 0.492876 0.954659 0.814595 11.00000 0.02927 0.05057 = 0.02553 -0.00011 0.01166 0.00316 C5 1 0.565442 1.023580 0.871475 11.00000 0.03268 0.08328 = 0.03044 0.00442 0.01315 -0.01027 AFIX 43 H5 2 0.613718 1.058019 0.861691 11.00000 -1.20000 AFIX 0 C6 1 0.567539 1.042500 0.943760 11.00000 0.03441 0.07613 = 0.02297 0.00051 0.00634 -0.00613 AFIX 43 H6 2 0.616950 1.091680 0.981549 11.00000 -1.20000 AFIX 0 C7 1 0.498513 0.990467 0.960976 11.00000 0.03243 0.06518 = 0.02674 -0.00398 0.01374 0.00141 C8 1 0.425244 0.923796 0.901680 11.00000 0.05707 0.16401 = 0.05605 -0.04650 0.04218 -0.05248 AFIX 43 H8 2 0.376544 0.889806 0.910973 11.00000 -1.20000 AFIX 0 C9 1 0.421840 0.905820 0.828736 11.00000 0.04987 0.14218 = 0.04707 -0.04586 0.03118 -0.04733 AFIX 43 H9 2 0.371537 0.860878 0.789981 11.00000 -1.20000 AFIX 0 C10 1 0.197564 0.736244 0.602210 11.00000 0.02074 0.02127 = 0.02468 0.00930 0.01040 0.00667 C11 1 0.168637 0.668256 0.660790 11.00000 0.02241 0.01408 = 0.01856 -0.00030 0.00878 -0.00057 C12 1 0.228025 0.567738 0.714968 11.00000 0.01999 0.02052 = 0.02272 0.00334 0.00985 0.00154 AFIX 43 H12 2 0.285881 0.553301 0.717691 11.00000 -1.20000 AFIX 0 C13 1 0.201683 0.488742 0.765033 11.00000 0.02179 0.01755 = 0.01339 -0.00060 0.00385 -0.00098 C14 1 0.116750 0.510914 0.763424 11.00000 0.02984 0.02613 = 0.02146 0.00720 0.01466 0.00227 AFIX 43 H14 2 0.099511 0.458383 0.797471 11.00000 -1.20000 AFIX 0 C15 1 0.058097 0.612876 0.710087 11.00000 0.02298 0.02688 = 0.02768 0.00704 0.01516 0.00491 AFIX 43 H15 2 0.000934 0.628834 0.708647 11.00000 -1.20000 AFIX 0 C16 1 0.082614 0.692568 0.658269 11.00000 0.02077 0.01653 = 0.01823 0.00174 0.00876 0.00029 C17 1 0.014954 0.796313 0.600451 11.00000 0.02200 0.01551 = 0.01442 -0.00166 0.00501 -0.00209 C18 1 0.171297 1.166682 0.694495 11.00000 0.03246 0.01917 = 0.01779 -0.00407 0.01080 -0.00451 C19 1 0.190696 1.144012 0.777446 11.00000 0.02723 0.02183 = 0.01748 -0.00109 0.01226 -0.00034 C20 1 0.164116 1.003207 0.797518 11.00000 0.04544 0.02453 = 0.03112 -0.00684 0.02031 -0.00911 AFIX 43 H20 2 0.133412 0.930632 0.759603 11.00000 -1.20000 AFIX 0 C21 1 0.182511 0.969570 0.872551 11.00000 0.05037 0.02354 = 0.03986 0.00499 0.02621 -0.00596 AFIX 43 H21 2 0.166138 0.873853 0.885592 11.00000 -1.20000 AFIX 0 C22 1 0.225346 1.079225 0.927849 11.00000 0.03684 0.02866 = 0.02501 0.00572 0.01910 0.00194 AFIX 43 H22 2 0.235719 1.058112 0.978267 11.00000 -1.20000 AFIX 0 C23 1 0.253623 1.220854 0.910569 11.00000 0.02117 0.02224 = 0.01620 0.00187 0.00970 0.00484 C24 1 0.236068 1.251173 0.834551 11.00000 0.01650 0.02034 = 0.01693 0.00522 0.00766 0.00352 C25 1 0.300600 1.333747 0.974501 11.00000 0.02038 0.03039 = 0.01433 0.00089 0.00480 0.00553 HKLF 4 REM 10723 in P2(1)/c REM wR2 = 0.0637, GooF = S = 1.012, Restrained GooF = 1.012 for all data REM R1 = 0.0280 for 4941 Fo > 4sig(Fo) and 0.0386 for all 5972 data REM 352 parameters refined using 0 restraints END WGHT 0.0204 1.5007 REM Highest difference peak 0.505, deepest hole -0.622, 1-sigma level 0.100 Q1 1 0.1388 0.7240 0.5407 11.00000 0.05 0.50 Q2 1 0.0944 1.0170 0.4990 11.00000 0.05 0.45 Q3 1 0.1312 1.4912 0.5390 11.00000 0.05 0.44 Q4 1 0.1737 1.1647 0.7434 11.00000 0.05 0.41 Q5 1 0.2363 1.1177 0.6512 11.00000 0.05 0.41 ; _shelx_res_checksum 8558 _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 Ce1 Ce 0.13445(2) 1.08935(2) 0.53701(2) 0.01577(5) Uani 1 1 d . . . . . N1 N 0.44856(17) 0.9764(3) 0.61818(15) 0.0349(6) Uani 1 1 d . . . . . H1 H 0.417062 1.003063 0.571390 0.042 Uiso 1 1 calc R . . . . N2 N 0.49016(17) 0.9408(3) 0.73919(14) 0.0319(6) Uani 1 1 d . . . . . O1 O 0.22678(13) 0.8740(2) 0.61166(11) 0.0253(4) Uani 1 1 d . . . . . O2 O 0.19200(17) 0.6488(3) 0.54870(12) 0.0374(6) Uani 1 1 d . . . . . O3 O 0.03400(12) 0.8648(2) 0.54965(10) 0.0205(4) Uani 1 1 d . . . . . O4 O -0.06168(13) 0.8108(2) 0.60005(11) 0.0264(5) Uani 1 1 d . . . . . O5 O 0.26557(12) 1.3912(2) 0.81663(10) 0.0208(4) Uani 1 1 d . . . . . O6 O 0.23437(14) 1.1959(2) 0.67517(11) 0.0287(5) Uani 1 1 d . . . . . O7 O 0.09103(14) 1.1419(3) 0.64566(11) 0.0310(5) Uani 1 1 d . . . . . O8 O 0.36840(15) 1.4051(3) 0.97794(12) 0.0412(6) Uani 1 1 d . . . . . O9 O 0.26934(13) 1.3454(3) 1.02479(11) 0.0292(5) Uani 1 1 d . . . . . O1W O 0.11268(17) 0.8745(3) 0.43735(13) 0.0388(6) Uani 1 1 d . . . . . H1WA H 0.131296 0.793040 0.464644 0.047 Uiso 1 1 d R . . . . H1WB H 0.055466 0.865320 0.416744 0.047 Uiso 1 1 d R . . . . O2W O 0.09616(17) 1.3837(2) 0.53692(13) 0.0393(6) Uani 1 1 d . . . . . H2WA H 0.079404 1.477448 0.524863 0.047 Uiso 1 1 d R . . . . H2WB H 0.103904 1.375938 0.583313 0.047 Uiso 1 1 d R . . . . C1 C 0.4245(2) 0.9954(4) 0.67480(18) 0.0359(8) Uani 1 1 d . . . . . H1A H 0.370609 1.039708 0.670796 0.043 Uiso 1 1 calc R . . . . C2 C 0.5318(2) 0.9073(4) 0.64564(18) 0.0340(7) Uani 1 1 d . . . . . H2 H 0.564144 0.881430 0.617308 0.041 Uiso 1 1 calc R . . . . C3 C 0.5582(2) 0.8835(4) 0.72087(18) 0.0315(7) Uani 1 1 d . . . . . H3 H 0.611925 0.837345 0.754310 0.038 Uiso 1 1 calc R . . . . C4 C 0.4929(2) 0.9547(4) 0.81459(18) 0.0351(8) Uani 1 1 d . . . . . C5 C 0.5654(2) 1.0236(5) 0.87147(19) 0.0488(10) Uani 1 1 d . . . . . H5 H 0.613718 1.058019 0.861691 0.059 Uiso 1 1 calc R . . . . C6 C 0.5675(2) 1.0425(5) 0.94376(19) 0.0464(10) Uani 1 1 d . . . . . H6 H 0.616950 1.091680 0.981549 0.056 Uiso 1 1 calc R . . . . C7 C 0.4985(2) 0.9905(5) 0.96098(18) 0.0410(9) Uani 1 1 d . . . . . C8 C 0.4252(3) 0.9238(7) 0.9017(3) 0.086(2) Uani 1 1 d . . . . . H8 H 0.376544 0.889806 0.910973 0.103 Uiso 1 1 calc R . . . . C9 C 0.4218(3) 0.9058(6) 0.8287(2) 0.0760(17) Uani 1 1 d . . . . . H9 H 0.371537 0.860878 0.789981 0.091 Uiso 1 1 calc R . . . . C10 C 0.19756(18) 0.7362(3) 0.60221(16) 0.0219(6) Uani 1 1 d . . . . . C11 C 0.16864(18) 0.6683(3) 0.66079(15) 0.0183(5) Uani 1 1 d . . . . . C12 C 0.22802(19) 0.5677(3) 0.71497(15) 0.0208(6) Uani 1 1 d . . . . . H12 H 0.285881 0.553301 0.717691 0.025 Uiso 1 1 calc R . . . . C13 C 0.20168(18) 0.4887(3) 0.76503(14) 0.0188(5) Uani 1 1 d . . . . . C14 C 0.11675(19) 0.5109(3) 0.76342(15) 0.0245(6) Uani 1 1 d . . . . . H14 H 0.099511 0.458383 0.797471 0.029 Uiso 1 1 calc R . . . . C15 C 0.0581(2) 0.6129(3) 0.71009(16) 0.0243(6) Uani 1 1 d . . . . . H15 H 0.000934 0.628834 0.708647 0.029 Uiso 1 1 calc R . . . . C16 C 0.08261(18) 0.6926(3) 0.65827(15) 0.0183(5) Uani 1 1 d . . . . . C17 C 0.01495(18) 0.7963(3) 0.60045(14) 0.0182(5) Uani 1 1 d . . . . . C18 C 0.1713(2) 1.1667(3) 0.69450(15) 0.0230(6) Uani 1 1 d . . . . . C19 C 0.19070(19) 1.1440(3) 0.77745(15) 0.0212(6) Uani 1 1 d . . . . . C20 C 0.1641(2) 1.0032(4) 0.79752(18) 0.0322(7) Uani 1 1 d . . . . . H20 H 0.133412 0.930632 0.759603 0.039 Uiso 1 1 calc R . . . . C21 C 0.1825(2) 0.9696(4) 0.87255(19) 0.0354(8) Uani 1 1 d . . . . . H21 H 0.166138 0.873853 0.885592 0.043 Uiso 1 1 calc R . . . . C22 C 0.2253(2) 1.0792(3) 0.92785(17) 0.0281(7) Uani 1 1 d . . . . . H22 H 0.235719 1.058112 0.978267 0.034 Uiso 1 1 calc R . . . . C23 C 0.25362(18) 1.2209(3) 0.91057(14) 0.0192(5) Uani 1 1 d . . . . . C24 C 0.23607(17) 1.2512(3) 0.83455(14) 0.0177(5) Uani 1 1 d . . . . . C25 C 0.30060(19) 1.3337(3) 0.97450(15) 0.0225(6) 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 Ce1 0.01664(8) 0.01683(8) 0.01336(8) 0.00141(6) 0.00581(6) -0.00025(6) N1 0.0275(14) 0.0499(18) 0.0228(13) 0.0057(12) 0.0062(11) 0.0031(13) N2 0.0237(13) 0.0462(17) 0.0237(13) 0.0023(11) 0.0079(11) 0.0022(12) O1 0.0197(10) 0.0240(11) 0.0298(11) 0.0096(8) 0.0081(9) -0.0004(8) O2 0.0647(17) 0.0254(11) 0.0367(13) 0.0050(10) 0.0357(13) 0.0073(11) O3 0.0191(10) 0.0218(10) 0.0200(10) 0.0061(8) 0.0076(8) -0.0001(8) O4 0.0227(11) 0.0353(12) 0.0238(10) 0.0093(9) 0.0123(9) 0.0073(9) O5 0.0202(10) 0.0193(10) 0.0186(9) 0.0075(7) 0.0040(8) -0.0007(8) O6 0.0301(11) 0.0371(12) 0.0194(10) -0.0043(9) 0.0107(9) -0.0094(10) O7 0.0282(12) 0.0440(13) 0.0211(11) -0.0073(9) 0.0106(9) -0.0062(10) O8 0.0382(14) 0.0646(18) 0.0245(11) -0.0134(11) 0.0167(11) -0.0228(12) O9 0.0257(11) 0.0449(13) 0.0203(10) -0.0073(9) 0.0129(9) 0.0028(10) O1W 0.0600(16) 0.0298(12) 0.0313(12) 0.0012(9) 0.0237(12) 0.0076(11) O2W 0.0573(16) 0.0230(12) 0.0351(13) -0.0025(9) 0.0168(12) 0.0006(11) C1 0.0243(16) 0.050(2) 0.0305(17) 0.0049(15) 0.0087(14) 0.0074(15) C2 0.0268(16) 0.046(2) 0.0300(17) -0.0002(15) 0.0131(14) 0.0022(15) C3 0.0205(15) 0.043(2) 0.0282(16) 0.0030(13) 0.0081(13) 0.0036(13) C4 0.0293(17) 0.051(2) 0.0255(16) -0.0001(14) 0.0117(14) 0.0032(15) C5 0.0327(19) 0.083(3) 0.0304(18) 0.0044(19) 0.0131(16) -0.0103(19) C6 0.034(2) 0.076(3) 0.0230(17) 0.0005(17) 0.0063(15) -0.0061(19) C7 0.0324(19) 0.065(3) 0.0267(18) -0.0040(17) 0.0137(15) 0.0014(18) C8 0.057(3) 0.164(6) 0.056(3) -0.047(3) 0.042(2) -0.052(3) C9 0.050(3) 0.142(5) 0.047(2) -0.046(3) 0.031(2) -0.047(3) C10 0.0207(14) 0.0213(15) 0.0247(14) 0.0093(11) 0.0104(12) 0.0067(11) C11 0.0224(14) 0.0141(13) 0.0186(13) -0.0003(10) 0.0088(11) -0.0006(11) C12 0.0200(14) 0.0205(14) 0.0227(14) 0.0033(11) 0.0099(12) 0.0015(11) C13 0.0218(14) 0.0175(13) 0.0134(12) -0.0006(10) 0.0038(11) -0.0010(11) C14 0.0298(16) 0.0261(16) 0.0215(14) 0.0072(12) 0.0147(13) 0.0023(13) C15 0.0230(15) 0.0269(16) 0.0277(15) 0.0070(12) 0.0152(13) 0.0049(12) C16 0.0208(14) 0.0165(13) 0.0182(13) 0.0017(10) 0.0088(11) 0.0003(11) C17 0.0220(14) 0.0155(13) 0.0144(12) -0.0017(10) 0.0050(11) -0.0021(11) C18 0.0325(16) 0.0192(14) 0.0178(14) -0.0041(11) 0.0108(13) -0.0045(12) C19 0.0272(15) 0.0218(14) 0.0175(13) -0.0011(11) 0.0123(12) -0.0003(12) C20 0.045(2) 0.0245(16) 0.0311(17) -0.0068(13) 0.0203(15) -0.0091(15) C21 0.050(2) 0.0235(16) 0.0399(19) 0.0050(14) 0.0262(17) -0.0060(15) C22 0.0368(17) 0.0287(16) 0.0250(15) 0.0057(12) 0.0191(14) 0.0019(14) C23 0.0212(14) 0.0222(14) 0.0162(13) 0.0019(10) 0.0097(11) 0.0048(11) C24 0.0165(13) 0.0203(14) 0.0169(13) 0.0052(10) 0.0077(11) 0.0035(11) C25 0.0204(14) 0.0304(16) 0.0143(13) 0.0009(11) 0.0048(11) 0.0055(12) 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' Ce Ce -0.2486 2.6331 '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 Ce1 O3 136.48(6) . 3_576 ? O1 Ce1 O3 68.93(6) . . ? O1 Ce1 O4 140.48(7) . 3_576 ? O1 Ce1 O6 72.53(7) . . ? O1 Ce1 O7 87.99(7) . . ? O1 Ce1 O1W 75.78(7) . . ? O1 Ce1 O2W 145.68(7) . . ? O1 Ce1 C17 149.96(7) . 3_576 ? O3 Ce1 O3 68.45(7) 3_576 . ? O3 Ce1 O6 108.06(6) . . ? O3 Ce1 O6 129.92(6) 3_576 . ? O3 Ce1 O2W 70.20(7) 3_576 . ? O3 Ce1 C17 90.86(7) . 3_576 ? O3 Ce1 C17 26.14(6) 3_576 3_576 ? O4 Ce1 O3 50.92(6) 3_576 3_576 ? O4 Ce1 O3 107.90(6) 3_576 . ? O4 Ce1 O6 138.80(7) 3_576 . ? O4 Ce1 O1W 67.08(7) 3_576 . ? O4 Ce1 O2W 70.41(7) 3_576 . ? O4 Ce1 C17 25.36(6) 3_576 3_576 ? O6 Ce1 C17 136.73(7) . 3_576 ? O7 Ce1 O3 69.42(6) . . ? O7 Ce1 O3 85.22(6) . 3_576 ? O7 Ce1 O4 129.08(7) . 3_576 ? O7 Ce1 O6 50.80(6) . . ? O7 Ce1 O1W 138.49(7) . . ? O7 Ce1 O2W 71.06(7) . . ? O7 Ce1 C17 106.00(7) . 3_576 ? O9 Ce1 O1 82.45(7) 4_585 . ? O9 Ce1 O3 132.82(6) 4_585 3_576 ? O9 Ce1 O3 145.89(7) 4_585 . ? O9 Ce1 O4 82.37(6) 4_585 3_576 ? O9 Ce1 O6 79.11(6) 4_585 . ? O9 Ce1 O7 129.42(7) 4_585 . ? O9 Ce1 O1W 86.57(8) 4_585 . ? O9 Ce1 O2W 90.14(8) 4_585 . ? O9 Ce1 C17 106.68(7) 4_585 3_576 ? O1W Ce1 O3 81.36(7) . 3_576 ? O1W Ce1 O3 69.10(7) . . ? O1W Ce1 O6 146.58(7) . . ? O1W Ce1 O2W 137.42(7) . . ? O1W Ce1 C17 76.29(7) . 3_576 ? O2W Ce1 O3 123.97(7) . . ? O2W Ce1 O6 73.16(7) . . ? O2W Ce1 C17 64.12(7) . 3_576 ? C1 N1 H1 125.5 . . ? C1 N1 C2 109.0(3) . . ? C2 N1 H1 125.5 . . ? C1 N2 C3 107.7(3) . . ? C1 N2 C4 125.5(3) . . ? C3 N2 C4 126.5(3) . . ? C10 O1 Ce1 121.64(17) . . ? Ce1 O3 Ce1 111.55(7) 3_576 . ? C17 O3 Ce1 140.41(17) . . ? C17 O3 Ce1 91.80(15) . 3_576 ? C17 O4 Ce1 94.07(15) . 3_576 ? C13 O5 C24 117.9(2) 1_565 . ? C18 O6 Ce1 89.59(16) . . ? C18 O7 Ce1 94.85(16) . . ? C25 O9 Ce1 140.90(18) . 4_586 ? Ce1 O1W H1WA 103.1 . . ? Ce1 O1W H1WB 101.3 . . ? H1WA O1W H1WB 104.5 . . ? Ce1 O2W H2WA 165.6 . . ? Ce1 O2W H2WB 89.6 . . ? H2WA O2W H2WB 104.5 . . ? N1 C1 N2 108.9(3) . . ? N1 C1 H1A 125.5 . . ? N2 C1 H1A 125.5 . . ? N1 C2 H2 126.2 . . ? C3 C2 N1 107.6(3) . . ? C3 C2 H2 126.2 . . ? N2 C3 H3 126.6 . . ? C2 C3 N2 106.8(3) . . ? C2 C3 H3 126.6 . . ? C5 C4 N2 119.7(3) . . ? C9 C4 N2 120.4(3) . . ? C9 C4 C5 119.8(3) . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.3(3) . . ? C6 C5 H5 119.8 . . ? C5 C6 H6 119.2 . . ? C7 C6 C5 121.7(3) . . ? C7 C6 H6 119.2 . . ? C6 C7 C7 121.5(4) . 3_677 ? C6 C7 C8 116.5(3) . . ? C8 C7 C7 121.9(4) . 3_677 ? C7 C8 H8 118.8 . . ? C7 C8 C9 122.3(4) . . ? C9 C8 H8 118.8 . . ? C4 C9 C8 119.3(4) . . ? C4 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O1 C10 C11 118.2(2) . . ? O2 C10 O1 125.3(3) . . ? O2 C10 C11 116.5(2) . . ? C12 C11 C10 117.7(2) . . ? C12 C11 C16 119.5(2) . . ? C16 C11 C10 122.6(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 C11 120.4(3) . . ? C13 C12 H12 119.8 . . ? O5 C13 C12 115.9(2) 1_545 . ? O5 C13 C14 123.1(2) 1_545 . ? C14 C13 C12 121.0(2) . . ? C13 C14 H14 120.7 . . ? C15 C14 C13 118.5(3) . . ? C15 C14 H14 120.7 . . ? C14 C15 H15 119.2 . . ? C14 C15 C16 121.6(3) . . ? C16 C15 H15 119.2 . . ? C11 C16 C15 118.9(2) . . ? C11 C16 C17 122.2(2) . . ? C15 C16 C17 118.8(2) . . ? O3 C17 Ce1 62.06(13) . 3_576 ? O3 C17 C16 120.2(2) . . ? O4 C17 Ce1 60.57(14) . 3_576 ? O4 C17 O3 120.5(2) . . ? O4 C17 C16 119.2(2) . . ? C16 C17 Ce1 162.72(18) . 3_576 ? O6 C18 O7 122.1(2) . . ? O6 C18 C19 120.3(3) . . ? O7 C18 C19 117.3(2) . . ? C20 C19 C18 117.1(2) . . ? C24 C19 C18 124.1(2) . . ? C24 C19 C20 118.8(2) . . ? C19 C20 H20 119.5 . . ? C21 C20 C19 121.1(3) . . ? C21 C20 H20 119.5 . . ? C20 C21 H21 120.5 . . ? C22 C21 C20 119.1(3) . . ? C22 C21 H21 120.5 . . ? C21 C22 H22 119.1 . . ? C21 C22 C23 121.8(3) . . ? C23 C22 H22 119.1 . . ? C22 C23 C24 118.2(3) . . ? C22 C23 C25 118.4(2) . . ? C24 C23 C25 123.4(2) . . ? O5 C24 C23 118.8(2) . . ? C19 C24 O5 120.2(2) . . ? C19 C24 C23 121.1(2) . . ? O8 C25 O9 123.5(3) . . ? O8 C25 C23 120.0(2) . . ? O9 C25 C23 116.4(3) . . ? 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 Ce1 O1 2.4358(19) . ? Ce1 O3 2.5760(18) 3_576 ? Ce1 O3 2.6043(18) . ? Ce1 O4 2.5450(19) 3_576 ? Ce1 O6 2.6322(19) . ? Ce1 O7 2.512(2) . ? Ce1 O9 2.3724(19) 4_585 ? Ce1 O1W 2.575(2) . ? Ce1 O2W 2.602(2) . ? Ce1 C17 2.915(3) 3_576 ? N1 H1 0.8600 . ? N1 C1 1.312(4) . ? N1 C2 1.367(4) . ? N2 C1 1.338(4) . ? N2 C3 1.386(4) . ? N2 C4 1.437(4) . ? O1 C10 1.259(3) . ? O2 C10 1.246(3) . ? O3 C17 1.285(3) . ? O4 C17 1.251(3) . ? O5 C13 1.380(3) 1_565 ? O5 C24 1.390(3) . ? O6 C18 1.255(3) . ? O7 C18 1.269(3) . ? O8 C25 1.240(3) . ? O9 C25 1.272(3) . ? O1W H1WA 0.8503 . ? O1W H1WB 0.8501 . ? O2W H2WA 0.8501 . ? O2W H2WB 0.8500 . ? C1 H1A 0.9300 . ? C2 H2 0.9300 . ? C2 C3 1.342(4) . ? C3 H3 0.9300 . ? C4 C5 1.365(5) . ? C4 C9 1.361(5) . ? C5 H5 0.9300 . ? C5 C6 1.386(5) . ? C6 H6 0.9300 . ? C6 C7 1.373(5) . ? C7 C7 1.491(6) 3_677 ? C7 C8 1.383(5) . ? C8 H8 0.9300 . ? C8 C9 1.389(5) . ? C9 H9 0.9300 . ? C10 C11 1.509(4) . ? C11 C12 1.387(4) . ? C11 C16 1.397(4) . ? C12 H12 0.9300 . ? C12 C13 1.385(4) . ? C13 C14 1.384(4) . ? C14 H14 0.9300 . ? C14 C15 1.382(4) . ? C15 H15 0.9300 . ? C15 C16 1.398(4) . ? C16 C17 1.490(4) . ? C18 C19 1.504(4) . ? C19 C20 1.392(4) . ? C19 C24 1.385(4) . ? C20 H20 0.9300 . ? C20 C21 1.376(4) . ? C21 H21 0.9300 . ? C21 C22 1.372(4) . ? C22 H22 0.9300 . ? C22 C23 1.389(4) . ? C23 C24 1.392(3) . ? C23 C25 1.500(4) . ? 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 O2 0.85 1.95 2.774(3) 164.2 . yes O1W H1WB O7 0.85 2.18 3.024(3) 173.9 3_576 yes O2W H2WA O2 0.85 2.24 2.714(3) 115.0 1_565 yes O2W H2WB O6 0.85 2.62 3.119(3) 118.4 . yes O2W H2WB O7 0.85 2.39 2.973(3) 125.9 . yes C1 H1A O1 0.93 2.56 3.108(4) 117.8 . yes C1 H1A O6 0.93 2.62 3.546(4) 171.1 . yes C2 H2 O5 0.93 2.52 3.072(4) 118.1 2_646 yes C2 H2 O8 0.93 2.51 3.396(4) 159.7 2_646 yes C3 H3 O6 0.93 2.60 3.515(4) 169.4 2_646 yes C14 H14 O4 0.93 2.62 3.553(3) 176.3 2_546 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 Ce1 O1 C10 O2 77.8(3) . . . . ? Ce1 O1 C10 C11 -103.7(2) . . . . ? Ce1 O3 C17 Ce1 127.9(2) . . . 3_576 ? Ce1 O3 C17 O4 111.2(3) . . . . ? Ce1 O3 C17 O4 -16.7(3) 3_576 . . . ? Ce1 O3 C17 C16 160.4(2) 3_576 . . . ? Ce1 O3 C17 C16 -71.7(3) . . . . ? Ce1 O4 C17 O3 16.9(3) 3_576 . . . ? Ce1 O4 C17 C16 -160.2(2) 3_576 . . . ? Ce1 O6 C18 O7 -16.4(3) . . . . ? Ce1 O6 C18 C19 157.4(2) . . . . ? Ce1 O7 C18 O6 17.3(3) . . . . ? Ce1 O7 C18 C19 -156.7(2) . . . . ? Ce1 O9 C25 O8 123.6(3) 4_586 . . . ? Ce1 O9 C25 C23 -59.4(4) 4_586 . . . ? N1 C2 C3 N2 -0.6(4) . . . . ? N2 C4 C5 C6 177.8(4) . . . . ? N2 C4 C9 C8 -178.5(4) . . . . ? O1 C10 C11 C12 -101.3(3) . . . . ? O1 C10 C11 C16 84.1(3) . . . . ? O2 C10 C11 C12 77.3(3) . . . . ? O2 C10 C11 C16 -97.3(3) . . . . ? O5 C13 C14 C15 179.1(3) 1_545 . . . ? O6 C18 C19 C20 -122.6(3) . . . . ? O6 C18 C19 C24 54.8(4) . . . . ? O7 C18 C19 C20 51.5(4) . . . . ? O7 C18 C19 C24 -131.2(3) . . . . ? C1 N1 C2 C3 0.3(4) . . . . ? C1 N2 C3 C2 0.7(4) . . . . ? C1 N2 C4 C5 -123.6(4) . . . . ? C1 N2 C4 C9 53.5(5) . . . . ? C2 N1 C1 N2 0.2(4) . . . . ? C3 N2 C1 N1 -0.6(4) . . . . ? C3 N2 C4 C5 49.4(5) . . . . ? C3 N2 C4 C9 -133.5(4) . . . . ? C4 N2 C1 N1 173.5(3) . . . . ? C4 N2 C3 C2 -173.3(3) . . . . ? C4 C5 C6 C7 1.3(6) . . . . ? C5 C4 C9 C8 -1.5(7) . . . . ? C5 C6 C7 C7 179.3(5) . . . 3_677 ? C5 C6 C7 C8 -2.5(7) . . . . ? C6 C7 C8 C9 1.7(8) . . . . ? C7 C7 C8 C9 179.9(5) 3_677 . . . ? C7 C8 C9 C4 0.2(9) . . . . ? C9 C4 C5 C6 0.7(6) . . . . ? C10 C11 C12 C13 -173.1(2) . . . . ? C10 C11 C16 C15 173.6(3) . . . . ? C10 C11 C16 C17 -4.2(4) . . . . ? C11 C12 C13 O5 179.8(2) . . . 1_545 ? C11 C12 C13 C14 -1.6(4) . . . . ? C11 C16 C17 Ce1 94.0(6) . . . 3_576 ? C11 C16 C17 O3 1.4(4) . . . . ? C11 C16 C17 O4 178.5(3) . . . . ? C12 C11 C16 C15 -0.8(4) . . . . ? C12 C11 C16 C17 -178.7(2) . . . . ? C12 C13 C14 C15 0.6(4) . . . . ? C13 O5 C24 C19 59.0(3) 1_565 . . . ? C13 O5 C24 C23 -121.5(3) 1_565 . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C14 C15 C16 C11 -0.1(4) . . . . ? C14 C15 C16 C17 177.8(3) . . . . ? C15 C16 C17 Ce1 -83.9(7) . . . 3_576 ? C15 C16 C17 O3 -176.5(2) . . . . ? C15 C16 C17 O4 0.6(4) . . . . ? C16 C11 C12 C13 1.7(4) . . . . ? C18 C19 C20 C21 177.2(3) . . . . ? C18 C19 C24 O5 1.1(4) . . . . ? C18 C19 C24 C23 -178.4(3) . . . . ? C19 C20 C21 C22 2.0(5) . . . . ? C20 C19 C24 O5 178.3(2) . . . . ? C20 C19 C24 C23 -1.1(4) . . . . ? C20 C21 C22 C23 -2.4(5) . . . . ? C21 C22 C23 C24 1.1(4) . . . . ? C21 C22 C23 C25 -179.5(3) . . . . ? C22 C23 C24 O5 -178.7(2) . . . . ? C22 C23 C24 C19 0.8(4) . . . . ? C22 C23 C25 O8 137.2(3) . . . . ? C22 C23 C25 O9 -40.0(4) . . . . ? C24 C19 C20 C21 -0.2(5) . . . . ? C24 C23 C25 O8 -43.5(4) . . . . ? C24 C23 C25 O9 139.4(3) . . . . ? C25 C23 C24 O5 1.9(4) . . . . ? C25 C23 C24 C19 -178.6(3) . . . . ?