#------------------------------------------------------------------------------ #$Date: 2020-08-20 04:47:43 +0300 (Thu, 20 Aug 2020) $ #$Revision: 255465 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705212.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_7705212 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 Nd O11, C9 H8 N2' _chemical_formula_sum 'C25 H18 N2 Nd O11' _chemical_formula_weight 666.65 _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 114.7074(16) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.2535(18) _cell_length_b 8.5688(9) _cell_length_c 19.213(2) _cell_measurement_reflns_used 7174 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.45 _cell_measurement_theta_min 2.65 _cell_volume 2430.9(5) _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 0.997 _diffrn_measured_fraction_theta_max 0.975 _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 0.0357 _diffrn_reflns_av_unetI/netI 0.0458 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 15058 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.445 _diffrn_reflns_theta_min 2.158 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.204 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.5637 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0997 before and 0.0525 after correction. The Ratio of minimum to maximum transmission is 0.7559. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.822 _exptl_crystal_description block _exptl_crystal_F_000 1320 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.662 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.098 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 352 _refine_ls_number_reflns 5981 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0257 _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^)+(0.0185P)^2^+0.8579P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.0621 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5179 _reflns_number_total 5981 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02120b2.cif _cod_data_source_block 10735 _cod_database_code 7705212 _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 0.879 _shelx_estimated_absorpt_t_min 0.473 _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: C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C14(H14), C15(H15), C20(H20), C21(H21), C22(H22), N1(H1A) ; _shelx_res_file ; TITL 10735 in P2(1)/c 10735.res created by SHELXL-2018/3 at 17:06:37 on 14-Aug-2020 CELL 0.71073 16.2535 8.5688 19.2127 90 114.7074 90 ZERR 4 0.0018 0.0009 0.0021 0 0.0016 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N Nd O UNIT 100 72 8 4 44 EQIV $1 1-X,1-Y,-Z EQIV $2 +X,1.5-Y,0.5+Z EQIV $3 1-X,2-Y,-Z EQIV $4 1-X,0.5+Y,0.5-Z EQIV $5 -1+X,+Y,+Z EQIV $6 1-X,0.5+Y,-0.5-Z L.S. 20 PLAN 5 SIZE 0.4 0.17 0.06 TEMP 23 HTAB C1 O2_$4 HTAB C1 O9_$2 HTAB C2 O3_$5 HTAB C2 O4_$5 HTAB C3 O2_$5 HTAB C14 O6_$6 HTAB O1W O1_$1 HTAB O1W O8_$1 HTAB O2W O8_$3 FREE Nd1 C17 FREE Nd1 C18 BOND $H CONF fmap 2 acta OMIT 8 0 0 OMIT 5 0 0 OMIT -14 0 10 OMIT -16 0 6 OMIT 3 0 0 OMIT -17 3 18 REM REM REM WGHT 0.018500 0.857900 FVAR 0.08414 ND1 4 0.633774 0.588294 0.036660 11.00000 0.01565 0.01594 = 0.01176 0.00125 0.00508 -0.00007 C1 1 0.076452 0.994722 0.325788 11.00000 0.02270 0.04615 = 0.02938 -0.00177 0.00612 -0.00379 AFIX 43 H1 2 0.130287 1.039334 0.329481 11.00000 -1.20000 AFIX 0 C2 1 -0.031037 0.906215 0.355422 11.00000 0.02291 0.04806 = 0.02864 -0.00009 0.01146 -0.00298 AFIX 43 H2 2 -0.063334 0.880085 0.383891 11.00000 -1.20000 AFIX 0 C3 1 -0.057735 0.883368 0.279801 11.00000 0.01996 0.04169 = 0.02540 -0.00371 0.00767 -0.00392 AFIX 43 H3 2 -0.111794 0.838173 0.246170 11.00000 -1.20000 AFIX 0 C4 1 0.007237 0.953141 0.185747 11.00000 0.02746 0.05054 = 0.02311 -0.00087 0.01015 -0.00365 C5 1 -0.065857 1.023297 0.128760 11.00000 0.03706 0.08180 = 0.02824 -0.00049 0.01490 0.01251 AFIX 43 H5 2 -0.113998 1.058567 0.138696 11.00000 -1.20000 AFIX 0 C6 1 -0.067831 1.041446 0.056677 11.00000 0.03313 0.07798 = 0.02176 -0.00152 0.00612 0.00478 AFIX 43 H6 2 -0.117451 1.090129 0.018700 11.00000 -1.20000 AFIX 0 C7 1 0.001373 0.989645 0.039567 11.00000 0.03041 0.06469 = 0.02833 0.00093 0.01374 -0.00537 C8 1 0.075167 0.923017 0.098206 11.00000 0.06241 0.15918 = 0.05076 0.04538 0.04291 0.05257 AFIX 43 H8 2 0.124036 0.889988 0.088736 11.00000 -1.20000 AFIX 0 C9 1 0.078207 0.903993 0.171502 11.00000 0.04798 0.14536 = 0.04332 0.04380 0.02809 0.04224 AFIX 43 H9 2 0.128358 0.858105 0.210180 11.00000 -1.20000 AFIX 0 C10 1 0.303448 0.763956 -0.100693 11.00000 0.01790 0.02055 = 0.02410 0.00815 0.00994 0.00710 C11 1 0.332316 0.832265 -0.159491 11.00000 0.01961 0.01460 = 0.01635 0.00005 0.00775 -0.00037 C12 1 0.272336 0.932581 -0.213969 11.00000 0.01751 0.01847 = 0.02221 0.00391 0.00764 0.00239 AFIX 43 H12 2 0.214229 0.946453 -0.216893 11.00000 -1.20000 AFIX 0 C13 1 0.299034 1.011967 -0.263944 11.00000 0.02299 0.01417 = 0.01085 0.00152 0.00292 0.00006 C14 1 0.384104 0.989981 -0.262022 11.00000 0.02865 0.02347 = 0.01901 0.00696 0.01266 0.00163 AFIX 43 H14 2 0.401380 1.043286 -0.295933 11.00000 -1.20000 AFIX 0 C15 1 0.443285 0.887671 -0.209019 11.00000 0.02075 0.02769 = 0.02338 0.00528 0.01262 0.00317 AFIX 43 H15 2 0.500471 0.871538 -0.207766 11.00000 -1.20000 AFIX 0 C16 1 0.418108 0.807574 -0.156909 11.00000 0.02004 0.01664 = 0.01374 0.00071 0.00471 -0.00041 C17 1 0.486783 0.703927 -0.099039 11.00000 0.02009 0.01374 = 0.01320 -0.00059 0.00442 0.00060 C18 1 0.671520 0.663357 0.193551 11.00000 0.02821 0.02007 = 0.01574 -0.00293 0.00923 -0.00381 C19 1 0.690498 0.641363 0.276441 11.00000 0.02485 0.02070 = 0.01474 0.00024 0.00845 0.00129 C20 1 0.664280 0.500483 0.296669 11.00000 0.04399 0.02275 = 0.02689 -0.00514 0.01810 -0.00943 AFIX 43 H20 2 0.634162 0.427144 0.258863 11.00000 -1.20000 AFIX 0 C21 1 0.682136 0.467591 0.371769 11.00000 0.04993 0.02197 = 0.03454 0.00571 0.02348 -0.00587 AFIX 43 H21 2 0.665757 0.371641 0.384776 11.00000 -1.20000 AFIX 0 C22 1 0.724449 0.577916 0.427485 11.00000 0.03641 0.02459 = 0.01924 0.00784 0.01649 0.00472 AFIX 43 H22 2 0.734588 0.556977 0.477923 11.00000 -1.20000 AFIX 0 C23 1 0.752363 0.720431 0.409651 11.00000 0.01793 0.02272 = 0.01495 0.00191 0.00805 0.00365 C24 1 0.798980 0.834419 0.473775 11.00000 0.02203 0.02880 = 0.01435 0.00189 0.00698 0.00541 C25 1 0.735506 0.750159 0.333513 11.00000 0.01563 0.01660 = 0.01458 0.00343 0.00565 0.00136 N1 3 0.052595 0.975149 0.382633 11.00000 0.02487 0.04923 = 0.02209 -0.00503 0.00511 -0.00559 AFIX 43 H1A 2 0.084431 1.001441 0.429492 11.00000 -1.20000 AFIX 0 N2 3 0.010267 0.939678 0.261709 11.00000 0.02000 0.04708 = 0.02198 -0.00171 0.00630 -0.00205 O1 5 0.590932 0.638273 0.144367 11.00000 0.02478 0.04276 = 0.01810 -0.00590 0.00898 -0.00708 O2 5 0.734388 0.693590 0.173645 11.00000 0.02854 0.03593 = 0.01816 -0.00535 0.01069 -0.00763 O3 5 0.765309 0.890167 0.315625 11.00000 0.01831 0.01843 = 0.01634 0.00644 0.00287 -0.00026 O4 5 0.866224 0.906767 0.477185 11.00000 0.03532 0.06488 = 0.02394 -0.01444 0.01614 -0.02231 O5 5 0.766773 0.845668 0.523632 11.00000 0.02137 0.04332 = 0.01974 -0.00736 0.01122 0.00202 O6 5 0.563048 0.689571 -0.098219 11.00000 0.01925 0.03554 = 0.02222 0.00995 0.00979 0.00668 O7 5 0.467072 0.635158 -0.048077 11.00000 0.01884 0.01985 = 0.01675 0.00483 0.00542 -0.00119 O8 5 0.308358 0.851317 -0.047239 11.00000 0.06172 0.02362 = 0.03235 0.00332 0.03333 0.00762 O9 5 0.274985 0.625260 -0.109777 11.00000 0.02006 0.02129 = 0.02783 0.00853 0.00840 0.00018 O1W 5 0.612738 0.378175 -0.062023 11.00000 0.05333 0.02691 = 0.02678 -0.00081 0.01861 0.00859 AFIX 3 H1WA 2 0.558558 0.357376 -0.092883 11.00000 -1.20000 H1WB 2 0.640208 0.292106 -0.046093 11.00000 -1.20000 AFIX 0 O2W 5 0.598275 0.879564 0.038300 11.00000 0.05177 0.02151 = 0.03835 -0.00568 0.02179 -0.00622 AFIX 3 H2WA 2 0.576885 0.891564 0.071460 11.00000 -1.20000 H2WB 2 0.624345 0.964174 0.036030 11.00000 -1.20000 AFIX 0 HKLF 4 REM 10735 in P2(1)/c REM wR2 = 0.0621, GooF = S = 1.031, Restrained GooF = 1.031 for all data REM R1 = 0.0257 for 5179 Fo > 4sig(Fo) and 0.0324 for all 5981 data REM 352 parameters refined using 0 restraints END WGHT 0.0181 0.8809 REM Highest difference peak 0.662, deepest hole -0.538, 1-sigma level 0.098 Q1 1 0.5980 0.5900 0.0563 11.00000 0.05 0.66 Q2 1 0.6741 0.5891 0.0148 11.00000 0.05 0.57 Q3 1 0.5041 0.6418 -0.0118 11.00000 0.05 0.49 Q4 1 0.3114 0.8755 -0.1934 11.00000 0.05 0.47 Q5 1 0.0433 0.8377 0.1529 11.00000 0.05 0.46 ; _shelx_res_checksum 57892 _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 Nd1 Nd 0.63377(2) 0.58829(2) 0.03666(2) 0.01467(5) Uani 1 1 d . . . . . C1 C 0.07645(19) 0.9947(4) 0.32579(16) 0.0344(7) Uani 1 1 d . . . . . H1 H 0.130287 1.039334 0.329481 0.041 Uiso 1 1 calc R . . . . C2 C -0.03104(19) 0.9062(4) 0.35542(17) 0.0330(7) Uani 1 1 d . . . . . H2 H -0.063334 0.880085 0.383891 0.040 Uiso 1 1 calc R . . . . C3 C -0.05773(19) 0.8834(3) 0.27980(16) 0.0296(6) Uani 1 1 d . . . . . H3 H -0.111794 0.838173 0.246170 0.036 Uiso 1 1 calc R . . . . C4 C 0.0072(2) 0.9531(4) 0.18575(16) 0.0338(7) Uani 1 1 d . . . . . C5 C -0.0659(2) 1.0233(5) 0.12876(17) 0.0486(9) Uani 1 1 d . . . . . H5 H -0.113998 1.058567 0.138696 0.058 Uiso 1 1 calc R . . . . C6 C -0.0678(2) 1.0414(5) 0.05668(17) 0.0461(9) Uani 1 1 d . . . . . H6 H -0.117451 1.090129 0.018700 0.055 Uiso 1 1 calc R . . . . C7 C 0.0014(2) 0.9896(4) 0.03957(16) 0.0407(8) Uani 1 1 d . . . . . C8 C 0.0752(3) 0.9230(6) 0.0982(2) 0.0843(18) Uani 1 1 d . . . . . H8 H 0.124036 0.889988 0.088736 0.101 Uiso 1 1 calc R . . . . C9 C 0.0782(3) 0.9040(6) 0.1715(2) 0.0758(16) Uani 1 1 d . . . . . H9 H 0.128358 0.858105 0.210180 0.091 Uiso 1 1 calc R . . . . C10 C 0.30345(16) 0.7640(3) -0.10069(14) 0.0205(5) Uani 1 1 d . . . . . C11 C 0.33232(16) 0.8323(3) -0.15949(13) 0.0168(5) Uani 1 1 d . . . . . C12 C 0.27234(17) 0.9326(3) -0.21397(14) 0.0196(5) Uani 1 1 d . . . . . H12 H 0.214229 0.946453 -0.216893 0.024 Uiso 1 1 calc R . . . . C13 C 0.29903(16) 1.0120(3) -0.26394(12) 0.0174(5) Uani 1 1 d . . . . . C14 C 0.38410(17) 0.9900(3) -0.26202(14) 0.0228(5) Uani 1 1 d . . . . . H14 H 0.401380 1.043286 -0.295933 0.027 Uiso 1 1 calc R . . . . C15 C 0.44329(18) 0.8877(3) -0.20902(15) 0.0228(5) Uani 1 1 d . . . . . H15 H 0.500471 0.871538 -0.207766 0.027 Uiso 1 1 calc R . . . . C16 C 0.41811(16) 0.8076(3) -0.15691(13) 0.0176(5) Uani 1 1 d . . . . . C17 C 0.48678(16) 0.7039(3) -0.09904(13) 0.0165(5) Uani 1 1 d . . . . . C18 C 0.67152(17) 0.6634(3) 0.19355(13) 0.0213(5) Uani 1 1 d . . . . . C19 C 0.69050(17) 0.6414(3) 0.27644(13) 0.0200(5) Uani 1 1 d . . . . . C20 C 0.6643(2) 0.5005(3) 0.29667(16) 0.0301(6) Uani 1 1 d . . . . . H20 H 0.634162 0.427144 0.258863 0.036 Uiso 1 1 calc R . . . . C21 C 0.6821(2) 0.4676(3) 0.37177(17) 0.0335(7) Uani 1 1 d . . . . . H21 H 0.665757 0.371641 0.384776 0.040 Uiso 1 1 calc R . . . . C22 C 0.72445(19) 0.5779(3) 0.42749(15) 0.0251(6) Uani 1 1 d . . . . . H22 H 0.734588 0.556977 0.477923 0.030 Uiso 1 1 calc R . . . . C23 C 0.75236(16) 0.7204(3) 0.40965(13) 0.0181(5) Uani 1 1 d . . . . . C24 C 0.79898(17) 0.8344(3) 0.47377(13) 0.0219(5) Uani 1 1 d . . . . . C25 C 0.73551(15) 0.7502(3) 0.33351(12) 0.0158(5) Uani 1 1 d . . . . . N1 N 0.05260(16) 0.9751(3) 0.38263(13) 0.0337(6) Uani 1 1 d . . . . . H1A H 0.084431 1.001441 0.429492 0.040 Uiso 1 1 calc R . . . . N2 N 0.01027(16) 0.9397(3) 0.26171(13) 0.0305(5) Uani 1 1 d . . . . . O1 O 0.59093(12) 0.6383(2) 0.14437(10) 0.0285(4) Uani 1 1 d . . . . . O2 O 0.73439(12) 0.6936(2) 0.17364(10) 0.0272(4) Uani 1 1 d . . . . . O3 O 0.76531(11) 0.89017(19) 0.31563(9) 0.0192(4) Uani 1 1 d . . . . . O4 O 0.86622(14) 0.9068(3) 0.47719(11) 0.0401(6) Uani 1 1 d . . . . . O5 O 0.76677(12) 0.8457(2) 0.52363(10) 0.0273(4) Uani 1 1 d . . . . . O6 O 0.56305(12) 0.6896(2) -0.09822(10) 0.0253(4) Uani 1 1 d . . . . . O7 O 0.46707(11) 0.6352(2) -0.04808(9) 0.0192(4) Uani 1 1 d . . . . . O8 O 0.30836(15) 0.8513(2) -0.04724(11) 0.0346(5) Uani 1 1 d . . . . . O9 O 0.27498(12) 0.6253(2) -0.10978(10) 0.0236(4) Uani 1 1 d . . . . . O1W O 0.61274(15) 0.3782(2) -0.06202(11) 0.0350(5) Uani 1 1 d . . . . . H1WA H 0.558558 0.357376 -0.092883 0.042 Uiso 1 1 d R . . . . H1WB H 0.640208 0.292106 -0.046093 0.042 Uiso 1 1 d R . . . . O2W O 0.59828(16) 0.8796(2) 0.03830(12) 0.0362(5) Uani 1 1 d . . . . . H2WA H 0.576885 0.891564 0.071460 0.043 Uiso 1 1 d R . . . . H2WB H 0.624345 0.964174 0.036030 0.043 Uiso 1 1 d 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 Nd1 0.01565(7) 0.01594(7) 0.01176(7) 0.00125(5) 0.00508(5) -0.00007(5) C1 0.0227(14) 0.0461(19) 0.0294(15) -0.0018(13) 0.0061(12) -0.0038(13) C2 0.0229(14) 0.0481(19) 0.0286(15) -0.0001(13) 0.0115(12) -0.0030(12) C3 0.0200(13) 0.0417(17) 0.0254(14) -0.0037(12) 0.0077(11) -0.0039(12) C4 0.0275(15) 0.0505(19) 0.0231(14) -0.0009(13) 0.0101(12) -0.0036(13) C5 0.0371(18) 0.082(3) 0.0282(16) -0.0005(17) 0.0149(14) 0.0125(18) C6 0.0331(17) 0.078(3) 0.0218(15) -0.0015(15) 0.0061(13) 0.0048(17) C7 0.0304(16) 0.065(2) 0.0283(16) 0.0009(15) 0.0137(13) -0.0054(15) C8 0.062(3) 0.159(5) 0.051(2) 0.045(3) 0.043(2) 0.053(3) C9 0.048(2) 0.145(5) 0.043(2) 0.044(2) 0.0281(19) 0.042(3) C10 0.0179(12) 0.0205(13) 0.0241(12) 0.0082(10) 0.0099(10) 0.0071(10) C11 0.0196(12) 0.0146(12) 0.0163(11) 0.0001(9) 0.0077(9) -0.0004(9) C12 0.0175(12) 0.0185(12) 0.0222(12) 0.0039(9) 0.0076(10) 0.0024(9) C13 0.0230(12) 0.0142(12) 0.0109(10) 0.0015(9) 0.0029(9) 0.0001(9) C14 0.0287(14) 0.0235(14) 0.0190(12) 0.0070(10) 0.0127(10) 0.0016(11) C15 0.0207(13) 0.0277(14) 0.0234(13) 0.0053(10) 0.0126(11) 0.0032(10) C16 0.0200(12) 0.0166(12) 0.0137(11) 0.0007(9) 0.0047(9) -0.0004(9) C17 0.0201(12) 0.0137(11) 0.0132(10) -0.0006(9) 0.0044(9) 0.0006(9) C18 0.0282(14) 0.0201(13) 0.0157(11) -0.0029(10) 0.0092(10) -0.0038(10) C19 0.0249(13) 0.0207(12) 0.0147(11) 0.0002(9) 0.0085(10) 0.0013(10) C20 0.0440(17) 0.0227(14) 0.0269(14) -0.0051(11) 0.0181(13) -0.0094(12) C21 0.0499(19) 0.0220(14) 0.0345(16) 0.0057(12) 0.0235(14) -0.0059(13) C22 0.0364(15) 0.0246(14) 0.0192(12) 0.0078(10) 0.0165(11) 0.0047(11) C23 0.0179(11) 0.0227(13) 0.0149(11) 0.0019(9) 0.0080(9) 0.0036(9) C24 0.0220(13) 0.0288(14) 0.0143(11) 0.0019(10) 0.0070(10) 0.0054(10) C25 0.0156(11) 0.0166(11) 0.0146(10) 0.0034(9) 0.0056(9) 0.0014(9) N1 0.0249(12) 0.0492(16) 0.0221(12) -0.0050(11) 0.0051(10) -0.0056(11) N2 0.0200(11) 0.0471(16) 0.0220(12) -0.0017(10) 0.0063(9) -0.0020(10) O1 0.0248(10) 0.0428(12) 0.0181(9) -0.0059(8) 0.0090(8) -0.0071(9) O2 0.0285(10) 0.0359(11) 0.0182(9) -0.0054(8) 0.0107(8) -0.0076(8) O3 0.0183(9) 0.0184(9) 0.0163(8) 0.0064(7) 0.0029(7) -0.0003(7) O4 0.0353(12) 0.0649(17) 0.0239(10) -0.0144(9) 0.0161(9) -0.0223(10) O5 0.0214(9) 0.0433(12) 0.0197(9) -0.0074(8) 0.0112(8) 0.0020(8) O6 0.0192(9) 0.0355(11) 0.0222(9) 0.0099(8) 0.0098(7) 0.0067(8) O7 0.0188(9) 0.0198(9) 0.0167(8) 0.0048(7) 0.0054(7) -0.0012(7) O8 0.0617(14) 0.0236(10) 0.0324(11) 0.0033(9) 0.0333(11) 0.0076(10) O9 0.0201(9) 0.0213(9) 0.0278(10) 0.0085(7) 0.0084(8) 0.0002(7) O1W 0.0533(14) 0.0269(11) 0.0268(10) -0.0008(8) 0.0186(10) 0.0086(9) O2W 0.0518(13) 0.0215(10) 0.0383(12) -0.0057(9) 0.0218(10) -0.0062(9) 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' Nd Nd -0.1943 3.0179 '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 Nd1 O2 51.35(6) . . ? O1 Nd1 O6 129.38(6) . . ? O1 Nd1 O7 69.43(6) . 3_665 ? O1 Nd1 O7 84.91(6) . . ? O1 Nd1 O1W 138.60(7) . . ? O1 Nd1 O2W 71.26(7) . . ? O5 Nd1 O1 129.75(6) 4_575 . ? O5 Nd1 O2 78.90(6) 4_575 . ? O5 Nd1 O6 81.45(6) 4_575 . ? O5 Nd1 O7 132.54(6) 4_575 . ? O5 Nd1 O7 146.24(6) 4_575 3_665 ? O5 Nd1 O9 82.83(6) 4_575 3_665 ? O5 Nd1 O1W 86.20(7) 4_575 . ? O5 Nd1 O2W 89.35(7) 4_575 . ? O6 Nd1 O2 138.15(6) . . ? O6 Nd1 O7 51.59(5) . . ? O6 Nd1 O7 108.07(5) . 3_665 ? O6 Nd1 O1W 67.20(6) . . ? O6 Nd1 O2W 70.61(6) . . ? O7 Nd1 O2 129.91(6) . . ? O7 Nd1 O2 108.79(5) 3_665 . ? O7 Nd1 O7 68.17(6) . 3_665 ? O7 Nd1 O2W 70.68(6) . . ? O9 Nd1 O1 87.92(7) 3_665 . ? O9 Nd1 O2 72.57(6) 3_665 . ? O9 Nd1 O6 140.44(6) 3_665 . ? O9 Nd1 O7 69.22(6) 3_665 3_665 ? O9 Nd1 O7 136.58(6) 3_665 . ? O9 Nd1 O1W 75.73(6) 3_665 . ? O9 Nd1 O2W 145.13(6) 3_665 . ? O1W Nd1 O2 146.32(6) . . ? O1W Nd1 O7 81.87(6) . . ? O1W Nd1 O7 69.23(6) . 3_665 ? O1W Nd1 O2W 137.77(6) . . ? O2W Nd1 O2 72.58(6) . . ? O2W Nd1 O7 124.41(6) . 3_665 ? N1 C1 H1 125.8 . . ? N1 C1 N2 108.5(3) . . ? N2 C1 H1 125.8 . . ? C3 C2 H2 126.4 . . ? C3 C2 N1 107.2(3) . . ? N1 C2 H2 126.4 . . ? C2 C3 H3 126.5 . . ? C2 C3 N2 106.9(2) . . ? N2 C3 H3 126.5 . . ? C5 C4 N2 119.6(3) . . ? C9 C4 C5 120.0(3) . . ? C9 C4 N2 120.4(3) . . ? C4 C5 H5 120.0 . . ? C4 C5 C6 119.9(3) . . ? C6 C5 H5 120.0 . . ? C5 C6 H6 119.1 . . ? C7 C6 C5 121.8(3) . . ? C7 C6 H6 119.1 . . ? C6 C7 C7 121.4(4) . 3_575 ? C6 C7 C8 117.3(3) . . ? C8 C7 C7 121.3(4) . 3_575 ? C7 C8 H8 119.2 . . ? C7 C8 C9 121.6(4) . . ? C9 C8 H8 119.2 . . ? C4 C9 C8 119.4(3) . . ? C4 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O8 C10 C11 116.8(2) . . ? O8 C10 O9 125.0(2) . . ? O9 C10 C11 118.2(2) . . ? C12 C11 C10 117.6(2) . . ? C12 C11 C16 119.9(2) . . ? C16 C11 C10 122.3(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 121.0(2) . . ? C14 C13 O3 123.4(2) . 3_675 ? O3 C13 C12 115.7(2) 3_675 . ? C13 C14 H14 120.4 . . ? C13 C14 C15 119.1(2) . . ? C15 C14 H14 120.4 . . ? C14 C15 H15 119.6 . . ? C14 C15 C16 120.9(2) . . ? C16 C15 H15 119.6 . . ? C11 C16 C15 119.0(2) . . ? C11 C16 C17 122.9(2) . . ? C15 C16 C17 118.0(2) . . ? O6 C17 C16 120.0(2) . . ? O6 C17 O7 120.6(2) . . ? O7 C17 C16 119.3(2) . . ? O1 C18 C19 117.2(2) . . ? O2 C18 C19 121.0(2) . . ? O2 C18 O1 121.6(2) . . ? C20 C19 C18 117.0(2) . . ? C20 C19 C25 118.9(2) . . ? C25 C19 C18 124.0(2) . . ? C19 C20 H20 119.5 . . ? C21 C20 C19 121.1(3) . . ? C21 C20 H20 119.5 . . ? C20 C21 H21 120.3 . . ? C20 C21 C22 119.5(3) . . ? C22 C21 H21 120.3 . . ? C21 C22 H22 119.4 . . ? C21 C22 C23 121.2(2) . . ? C23 C22 H22 119.4 . . ? C22 C23 C24 118.1(2) . . ? C22 C23 C25 118.4(2) . . ? C25 C23 C24 123.4(2) . . ? O4 C24 C23 120.1(2) . . ? O4 C24 O5 123.8(2) . . ? O5 C24 C23 116.1(2) . . ? C19 C25 C23 120.8(2) . . ? O3 C25 C19 120.4(2) . . ? O3 C25 C23 118.8(2) . . ? C1 N1 C2 109.2(2) . . ? C1 N1 H1A 125.4 . . ? C2 N1 H1A 125.4 . . ? C1 N2 C3 108.2(2) . . ? C1 N2 C4 125.2(3) . . ? C3 N2 C4 126.2(2) . . ? C18 O1 Nd1 95.04(15) . . ? C18 O2 Nd1 89.38(14) . . ? C13 O3 C25 117.62(18) 3_675 . ? C24 O5 Nd1 141.76(16) . 4_576 ? C17 O6 Nd1 94.10(14) . . ? Nd1 O7 Nd1 111.84(6) . 3_665 ? C17 O7 Nd1 140.14(15) . 3_665 ? C17 O7 Nd1 91.25(13) . . ? C10 O9 Nd1 122.39(15) . 3_665 ? Nd1 O1W H1WA 116.6 . . ? Nd1 O1W H1WB 117.5 . . ? H1WA O1W H1WB 107.7 . . ? Nd1 O2W H2WA 106.9 . . ? Nd1 O2W H2WB 135.2 . . ? H2WA O2W H2WB 107.7 . . ? 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 Nd1 O1 2.4809(18) . ? Nd1 O2 2.6109(17) . ? Nd1 O5 2.3469(18) 4_575 ? Nd1 O6 2.5099(17) . ? Nd1 O7 2.5427(16) . ? Nd1 O7 2.5888(17) 3_665 ? Nd1 O9 2.4041(17) 3_665 ? Nd1 O1W 2.5321(19) . ? Nd1 O2W 2.5648(19) . ? C1 H1 0.9300 . ? C1 N1 1.313(4) . ? C1 N2 1.337(3) . ? C2 H2 0.9300 . ? C2 C3 1.346(4) . ? C2 N1 1.370(4) . ? C3 H3 0.9300 . ? C3 N2 1.377(4) . ? C4 C5 1.373(4) . ? C4 C9 1.359(5) . ? C4 N2 1.444(4) . ? C5 H5 0.9300 . ? C5 C6 1.381(4) . ? C6 H6 0.9300 . ? C6 C7 1.371(5) . ? C7 C7 1.513(6) 3_575 ? C7 C8 1.380(5) . ? C8 H8 0.9300 . ? C8 C9 1.398(5) . ? C9 H9 0.9300 . ? C10 C11 1.511(3) . ? C10 O8 1.246(3) . ? C10 O9 1.261(3) . ? C11 C12 1.390(3) . ? C11 C16 1.391(3) . ? C12 H12 0.9300 . ? C12 C13 1.386(3) . ? C13 C14 1.381(3) . ? C13 O3 1.384(3) 3_675 ? C14 H14 0.9300 . ? C14 C15 1.383(3) . ? C15 H15 0.9300 . ? C15 C16 1.408(3) . ? C16 C17 1.494(3) . ? C17 O6 1.239(3) . ? C17 O7 1.293(3) . ? C18 C19 1.502(3) . ? C18 O1 1.273(3) . ? C18 O2 1.259(3) . ? C19 C20 1.389(4) . ? C19 C25 1.391(3) . ? C20 H20 0.9300 . ? C20 C21 1.377(4) . ? C21 H21 0.9300 . ? C21 C22 1.377(4) . ? C22 H22 0.9300 . ? C22 C23 1.394(3) . ? C23 C24 1.505(3) . ? C23 C25 1.395(3) . ? C24 O4 1.234(3) . ? C24 O5 1.273(3) . ? C25 O3 1.390(3) . ? N1 H1A 0.8600 . ? O1W H1WA 0.8499 . ? O1W H1WB 0.8501 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? 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 C1 H1 O2 0.93 2.59 3.511(4) 171.8 2_655 yes C1 H1 O9 0.93 2.57 3.108(3) 117.6 4_576 yes C2 H2 O3 0.93 2.54 3.073(3) 117.1 1_455 yes C2 H2 O4 0.93 2.51 3.395(4) 159.5 1_455 yes C3 H3 O2 0.93 2.61 3.530(3) 169.9 1_455 yes C14 H14 O6 0.93 2.65 3.578(3) 175.2 2_654 yes O1W H1WA O1 0.85 2.21 3.017(3) 159.1 3_665 yes O1W H1WB O8 0.85 2.04 2.769(3) 143.0 3_665 yes O2W H2WB O8 0.85 1.88 2.726(3) 171.3 3_675 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 C2 C3 N2 C1 0.2(3) . . . . ? C2 C3 N2 C4 -173.7(3) . . . . ? C3 C2 N1 C1 0.3(4) . . . . ? C4 C5 C6 C7 0.7(6) . . . . ? C5 C4 C9 C8 -1.2(7) . . . . ? C5 C4 N2 C1 -123.3(4) . . . . ? C5 C4 N2 C3 49.5(5) . . . . ? C5 C6 C7 C7 -179.9(4) . . . 3_575 ? C5 C6 C7 C8 -2.2(6) . . . . ? C6 C7 C8 C9 2.1(7) . . . . ? C7 C7 C8 C9 179.8(5) 3_575 . . . ? C7 C8 C9 C4 -0.5(8) . . . . ? C9 C4 C5 C6 1.1(6) . . . . ? C9 C4 N2 C1 53.4(5) . . . . ? C9 C4 N2 C3 -133.8(4) . . . . ? C10 C11 C12 C13 172.9(2) . . . . ? C10 C11 C16 C15 -173.6(2) . . . . ? C10 C11 C16 C17 3.9(4) . . . . ? C11 C10 O9 Nd1 103.2(2) . . . 3_665 ? C11 C12 C13 C14 1.8(4) . . . . ? C11 C12 C13 O3 -179.5(2) . . . 3_675 ? C11 C16 C17 O6 -178.1(2) . . . . ? C11 C16 C17 O7 -1.0(3) . . . . ? C12 C11 C16 C15 1.2(4) . . . . ? C12 C11 C16 C17 178.8(2) . . . . ? C12 C13 C14 C15 -0.3(4) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C14 C15 C16 C11 0.2(4) . . . . ? C14 C15 C16 C17 -177.5(2) . . . . ? C15 C16 C17 O6 -0.5(3) . . . . ? C15 C16 C17 O7 176.5(2) . . . . ? C16 C11 C12 C13 -2.2(4) . . . . ? C16 C17 O6 Nd1 160.74(18) . . . . ? C16 C17 O7 Nd1 -161.01(18) . . . . ? C16 C17 O7 Nd1 71.6(3) . . . 3_665 ? C18 C19 C20 C21 177.4(3) . . . . ? C18 C19 C25 C23 -178.7(2) . . . . ? C18 C19 C25 O3 0.7(4) . . . . ? C19 C18 O1 Nd1 -157.38(19) . . . . ? C19 C18 O2 Nd1 158.1(2) . . . . ? C19 C20 C21 C22 1.8(5) . . . . ? C19 C25 O3 C13 59.7(3) . . . 3_675 ? C20 C19 C25 C23 -1.5(4) . . . . ? C20 C19 C25 O3 177.9(2) . . . . ? C20 C21 C22 C23 -2.2(4) . . . . ? C21 C22 C23 C24 -179.4(3) . . . . ? C21 C22 C23 C25 0.8(4) . . . . ? C22 C23 C24 O4 137.5(3) . . . . ? C22 C23 C24 O5 -40.2(3) . . . . ? C22 C23 C25 C19 1.1(4) . . . . ? C22 C23 C25 O3 -178.3(2) . . . . ? C23 C24 O5 Nd1 -60.6(4) . . . 4_576 ? C23 C25 O3 C13 -120.9(2) . . . 3_675 ? C24 C23 C25 C19 -178.7(2) . . . . ? C24 C23 C25 O3 1.9(3) . . . . ? C25 C19 C20 C21 0.0(4) . . . . ? C25 C23 C24 O4 -42.7(4) . . . . ? C25 C23 C24 O5 139.6(2) . . . . ? N1 C1 N2 C3 0.0(4) . . . . ? N1 C1 N2 C4 173.9(3) . . . . ? N1 C2 C3 N2 -0.3(3) . . . . ? N2 C1 N1 C2 -0.2(4) . . . . ? N2 C4 C5 C6 177.8(3) . . . . ? N2 C4 C9 C8 -177.8(4) . . . . ? O1 C18 C19 C20 52.0(3) . . . . ? O1 C18 C19 C25 -130.8(3) . . . . ? O1 C18 O2 Nd1 -16.3(3) . . . . ? O2 C18 C19 C20 -122.7(3) . . . . ? O2 C18 C19 C25 54.5(4) . . . . ? O2 C18 O1 Nd1 17.3(3) . . . . ? O3 C13 C14 C15 -178.9(2) 3_675 . . . ? O4 C24 O5 Nd1 121.8(3) . . . 4_576 ? O6 C17 O7 Nd1 -111.3(2) . . . 3_665 ? O6 C17 O7 Nd1 16.0(2) . . . . ? O7 C17 O6 Nd1 -16.3(2) . . . . ? O8 C10 C11 C12 -77.1(3) . . . . ? O8 C10 C11 C16 97.9(3) . . . . ? O8 C10 O9 Nd1 -78.1(3) . . . 3_665 ? O9 C10 C11 C12 101.7(3) . . . . ? O9 C10 C11 C16 -83.3(3) . . . . ?