#------------------------------------------------------------------------------ #$Date: 2020-08-20 04:47:43 +0300 (Thu, 20 Aug 2020) $ #$Revision: 255465 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705214.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_7705214 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 Sm, C9 H8 N2' _chemical_formula_sum 'C25 H18 N2 O11 Sm' _chemical_formula_weight 672.76 _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 114.7534(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.2397(14) _cell_length_b 8.5555(7) _cell_length_c 19.2033(17) _cell_measurement_reflns_used 8561 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.24 _cell_measurement_theta_min 2.16 _cell_volume 2422.9(4) _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 0.975 _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 0.0388 _diffrn_reflns_av_unetI/netI 0.0517 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 14632 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.252 _diffrn_reflns_theta_min 1.381 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.492 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.4760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1412 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.6383. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.844 _exptl_crystal_description block _exptl_crystal_F_000 1328 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.06 _refine_diff_density_max 1.282 _refine_diff_density_min -1.310 _refine_diff_density_rms 0.156 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 352 _refine_ls_number_reflns 5862 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0323 _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^)+(0.0517P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.0931 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5147 _reflns_number_total 5862 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02120b2.cif _cod_data_source_block 10682 _cod_database_code 7705214 _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 0.865 _shelx_estimated_absorpt_t_min 0.407 _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), C2(H2A), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C20(H20), C21(H21), C23(H23) ; _shelx_res_file ; TITL 10682 in P2(1)/c 10682.res created by SHELXL-2018/3 at 17:07:44 on 14-Aug-2020 CELL 0.71073 16.2397 8.5555 19.2033 90 114.7534 90 ZERR 4 0.0014 0.0007 0.0017 0 0.0012 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O Sm UNIT 100 72 8 44 4 EQIV $1 -X,1-Y,2-Z EQIV $2 +X,1+Y,+Z L.S. 40 PLAN 3 SIZE 0.44 0.26 0.06 TEMP 23 HTAB O2W O1_$1 HTAB O1W O9_$2 FREE Sm1 C10 FREE Sm1 C18 BOND $H CONF fmap 2 acta OMIT 0 3 1 OMIT 12 2 3 OMIT 7 0 12 OMIT 7 0 14 OMIT -5 9 10 OMIT 15 4 7 OMIT 6 0 16 OMIT -18 2 15 OMIT -13 0 14 OMIT 5 0 20 OMIT -11 0 8 OMIT -19 3 12 REM REM REM WGHT 0.051700 FVAR 0.08573 SM1 5 0.133385 0.587796 1.036323 11.00000 0.01618 0.01460 = 0.01210 0.00127 0.00612 0.00018 N1 3 0.489266 0.438221 0.237919 11.00000 0.02428 0.04173 = 0.02406 0.00384 0.01084 0.00211 N2 3 0.446544 0.474107 0.116846 11.00000 0.02537 0.04622 = 0.02129 0.00605 0.00560 0.00550 AFIX 43 H2 2 0.414396 0.499895 0.069909 11.00000 -1.20000 AFIX 0 O1 4 0.091582 0.633983 1.143285 11.00000 0.02580 0.03845 = 0.01705 -0.00493 0.00860 -0.00541 O2 4 0.235034 0.691642 1.173105 11.00000 0.02919 0.03276 = 0.02132 -0.00521 0.01335 -0.00930 O3 4 0.264839 0.610445 0.814873 11.00000 0.01835 0.01849 = 0.01730 -0.00748 0.00385 0.00084 O4 4 0.364403 0.592157 0.976312 11.00000 0.03426 0.06131 = 0.02428 0.01391 0.01582 0.02314 O5 4 0.264378 0.652809 1.022805 11.00000 0.02328 0.03925 = 0.01760 0.00701 0.01055 -0.00095 O6 4 -0.031878 0.635924 0.953530 11.00000 0.01991 0.02065 = 0.01798 0.00607 0.00670 0.00069 O7 4 0.064132 0.691207 0.903266 11.00000 0.02286 0.03244 = 0.02283 0.00848 0.01131 0.00572 O8 4 0.223919 0.377044 1.108662 11.00000 0.01876 0.02086 = 0.02616 0.00691 0.00741 -0.00094 O9 4 0.192786 0.148627 1.047027 11.00000 0.06695 0.02165 = 0.03339 0.00424 0.03649 0.00752 O1W 4 0.100070 0.876365 1.039292 11.00000 0.05157 0.02063 = 0.03942 -0.00479 0.02248 -0.00569 AFIX 3 H1WA 2 0.061090 0.902655 1.055932 11.00000 -1.20000 H1WB 2 0.121090 0.959595 1.028762 11.00000 -1.20000 AFIX 0 O2W 4 0.113536 0.379699 0.938425 11.00000 0.05596 0.02449 = 0.02926 -0.00021 0.02646 0.00042 AFIX 3 H2WA 2 0.062986 0.332059 0.928155 11.00000 -1.20000 H2WB 2 0.107386 0.427479 0.897614 11.00000 -1.20000 AFIX 0 C1 1 0.492497 0.453549 0.313628 11.00000 0.02742 0.05031 = 0.02493 0.00207 0.01218 0.00397 C2 1 0.420999 0.404564 0.327828 11.00000 0.04911 0.14214 = 0.04249 -0.04185 0.03101 -0.03994 AFIX 43 H2A 2 0.370641 0.358766 0.289178 11.00000 -1.20000 AFIX 0 C3 1 0.424576 0.424293 0.401537 11.00000 0.05907 0.15997 = 0.05076 -0.04521 0.04203 -0.05226 AFIX 43 H3 2 0.375405 0.392229 0.410873 11.00000 -1.20000 AFIX 0 C4 1 0.498118 0.489262 0.460318 11.00000 0.03278 0.06848 = 0.02258 -0.00212 0.01346 0.00289 C5 1 0.568407 0.540475 0.443471 11.00000 0.03121 0.07755 = 0.02246 0.00218 0.00620 -0.00758 AFIX 43 H5 2 0.618308 0.588570 0.481576 11.00000 -1.20000 AFIX 0 C6 1 0.566158 0.521763 0.371186 11.00000 0.03299 0.07882 = 0.02745 -0.00077 0.01329 -0.01013 AFIX 43 H6 2 0.614782 0.555547 0.361488 11.00000 -1.20000 AFIX 0 C7 1 0.557522 0.382163 0.219704 11.00000 0.02131 0.03890 = 0.02674 0.00348 0.00907 0.00157 AFIX 43 H7 2 0.611664 0.336643 0.253202 11.00000 -1.20000 AFIX 0 C8 1 0.530292 0.406358 0.143496 11.00000 0.02613 0.04226 = 0.02648 -0.00032 0.01100 0.00407 AFIX 43 H8 2 0.562547 0.381517 0.114801 11.00000 -1.20000 AFIX 0 C9 1 0.422370 0.494046 0.173459 11.00000 0.02093 0.04851 = 0.02694 0.00314 0.00663 0.00484 AFIX 43 H9 2 0.368501 0.538858 0.169726 11.00000 -1.20000 AFIX 0 C10 1 0.171549 0.660379 1.192603 11.00000 0.03058 0.01670 = 0.01698 -0.00416 0.01199 -0.00352 C11 1 0.190631 0.859915 0.775479 11.00000 0.02506 0.01951 = 0.01408 -0.00062 0.01004 0.00009 C12 1 0.164085 1.002156 0.795871 11.00000 0.04425 0.01916 = 0.02690 0.00385 0.01784 0.00884 AFIX 43 H12 2 0.134398 1.076177 0.758191 11.00000 -1.20000 AFIX 0 C13 1 0.181469 1.033774 0.871242 11.00000 0.04970 0.02063 = 0.03352 -0.00353 0.02427 0.00653 AFIX 43 H13 2 0.164711 1.129408 0.884398 11.00000 -1.20000 AFIX 0 C14 1 0.223900 0.922587 0.927045 11.00000 0.03162 0.02487 = 0.01838 -0.00473 0.01373 -0.00129 AFIX 43 H14 2 0.234362 0.943444 0.977595 11.00000 -1.20000 AFIX 0 C15 1 0.251182 0.780331 0.908982 11.00000 0.01866 0.01921 = 0.01480 -0.00210 0.00829 -0.00341 C16 1 0.235411 0.750555 0.832964 11.00000 0.01560 0.01528 = 0.01595 -0.00334 0.00737 -0.00005 C17 1 0.296778 0.664910 0.973202 11.00000 0.02422 0.02302 = 0.01557 -0.00095 0.00899 -0.00181 C18 1 -0.013003 0.703976 0.902529 11.00000 0.02160 0.01597 = 0.01270 0.00004 0.00515 0.00023 C19 1 0.081217 0.192090 1.155925 11.00000 0.02133 0.01379 = 0.01518 0.00099 0.00701 0.00113 C20 1 0.056192 0.387861 0.707847 11.00000 0.02010 0.02603 = 0.02443 -0.00520 0.01206 -0.00215 AFIX 43 H20 2 -0.001023 0.371203 0.706551 11.00000 -1.20000 AFIX 0 C21 1 0.114883 0.490979 0.760938 11.00000 0.03015 0.02305 = 0.02028 -0.00972 0.01496 -0.00319 AFIX 43 H21 2 0.097343 0.544660 0.794627 11.00000 -1.20000 AFIX 0 C22 1 0.200301 0.512607 0.762876 11.00000 0.02041 0.01486 = 0.01347 -0.00221 0.00486 -0.00058 C23 1 0.227603 0.067844 1.213252 11.00000 0.01802 0.01832 = 0.02169 0.00449 0.00897 0.00311 AFIX 43 H23 2 0.286026 0.054496 1.216707 11.00000 -1.20000 AFIX 0 C24 1 0.167723 0.168265 1.158444 11.00000 0.02123 0.01294 = 0.01536 0.00160 0.00846 0.00083 C25 1 0.196198 0.237309 1.099830 11.00000 0.01890 0.01569 = 0.02535 0.00750 0.01099 0.00578 HKLF 4 REM 10682 in P2(1)/c REM wR2 = 0.0931, GooF = S = 1.072, Restrained GooF = 1.072 for all data REM R1 = 0.0323 for 5147 Fo > 4sig(Fo) and 0.0376 for all 5862 data REM 352 parameters refined using 0 restraints END WGHT 0.0517 0.0000 REM Highest difference peak 1.282, deepest hole -1.310, 1-sigma level 0.156 Q1 1 0.0814 0.6446 1.0319 11.00000 0.05 1.28 Q2 1 0.0824 0.5252 1.0335 11.00000 0.05 1.27 Q3 1 0.1817 0.6468 1.0400 11.00000 0.05 1.17 ; _shelx_res_checksum 47205 _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 Sm1 Sm 0.13339(2) 0.58780(2) 1.03632(2) 0.01423(7) Uani 1 1 d . . . . . N1 N 0.4893(2) 0.4382(4) 0.23792(17) 0.0298(7) Uani 1 1 d . . . . . N2 N 0.4465(2) 0.4741(4) 0.11685(16) 0.0324(7) Uani 1 1 d . . . . . H2 H 0.414396 0.499895 0.069909 0.039 Uiso 1 1 calc R . . . . O1 O 0.09158(16) 0.6340(3) 1.14329(12) 0.0272(5) Uani 1 1 d . . . . . O2 O 0.23503(16) 0.6916(3) 1.17310(13) 0.0268(5) Uani 1 1 d . . . . . O3 O 0.26484(15) 0.6104(2) 0.81487(12) 0.0193(5) Uani 1 1 d . . . . . O4 O 0.36440(19) 0.5922(3) 0.97631(16) 0.0387(8) Uani 1 1 d . . . . . O5 O 0.26438(16) 0.6528(3) 1.02281(12) 0.0260(5) Uani 1 1 d . . . . . O6 O -0.03188(15) 0.6359(3) 0.95353(11) 0.0199(4) Uani 1 1 d . . . . . O7 O 0.06413(15) 0.6912(3) 0.90327(13) 0.0255(5) Uani 1 1 d . . . . . O8 O 0.22392(15) 0.3770(3) 1.10866(13) 0.0226(5) Uani 1 1 d . . . . . O9 O 0.1928(2) 0.1486(3) 1.04703(14) 0.0354(6) Uani 1 1 d . . . . . O1W O 0.1001(2) 0.8764(3) 1.03929(15) 0.0361(6) Uani 1 1 d . . . . . H1WA H 0.061090 0.902655 1.055932 0.043 Uiso 1 1 d R . . . . H1WB H 0.121090 0.959595 1.028762 0.043 Uiso 1 1 d R . . . . O2W O 0.1135(2) 0.3797(3) 0.93842(15) 0.0336(6) Uani 1 1 d . . . . . H2WA H 0.062986 0.332059 0.928155 0.040 Uiso 1 1 d R . . . . H2WB H 0.107386 0.427479 0.897614 0.040 Uiso 1 1 d R . . . . C1 C 0.4925(3) 0.4535(5) 0.3136(2) 0.0338(8) Uani 1 1 d . . . . . C2 C 0.4210(4) 0.4046(7) 0.3278(3) 0.074(2) Uani 1 1 d . . . . . H2A H 0.370641 0.358766 0.289178 0.089 Uiso 1 1 calc R . . . . C3 C 0.4246(4) 0.4243(8) 0.4015(3) 0.083(2) Uani 1 1 d . . . . . H3 H 0.375405 0.392229 0.410873 0.100 Uiso 1 1 calc R . . . . C4 C 0.4981(3) 0.4893(6) 0.4603(2) 0.0406(10) Uani 1 1 d . . . . . C5 C 0.5684(3) 0.5405(6) 0.4435(2) 0.0454(10) Uani 1 1 d . . . . . H5 H 0.618308 0.588570 0.481576 0.055 Uiso 1 1 calc R . . . . C6 C 0.5662(3) 0.5218(6) 0.3712(2) 0.0462(11) Uani 1 1 d . . . . . H6 H 0.614782 0.555547 0.361488 0.055 Uiso 1 1 calc R . . . . C7 C 0.5575(3) 0.3822(4) 0.2197(2) 0.0293(8) Uani 1 1 d . . . . . H7 H 0.611664 0.336643 0.253202 0.035 Uiso 1 1 calc R . . . . C8 C 0.5303(3) 0.4064(4) 0.1435(2) 0.0316(8) Uani 1 1 d . . . . . H8 H 0.562547 0.381517 0.114801 0.038 Uiso 1 1 calc R . . . . C9 C 0.4224(2) 0.4940(5) 0.1735(2) 0.0333(8) Uani 1 1 d . . . . . H9 H 0.368501 0.538858 0.169726 0.040 Uiso 1 1 calc R . . . . C10 C 0.1715(2) 0.6604(4) 1.19260(17) 0.0207(6) Uani 1 1 d . . . . . C11 C 0.1906(2) 0.8599(4) 0.77548(16) 0.0189(6) Uani 1 1 d . . . . . C12 C 0.1641(3) 1.0022(4) 0.7959(2) 0.0291(8) Uani 1 1 d . . . . . H12 H 0.134398 1.076177 0.758191 0.035 Uiso 1 1 calc R . . . . C13 C 0.1815(3) 1.0338(4) 0.8712(2) 0.0323(8) Uani 1 1 d . . . . . H13 H 0.164711 1.129408 0.884398 0.039 Uiso 1 1 calc R . . . . C14 C 0.2239(3) 0.9226(4) 0.9270(2) 0.0239(7) Uani 1 1 d . . . . . H14 H 0.234362 0.943444 0.977595 0.029 Uiso 1 1 calc R . . . . C15 C 0.2512(2) 0.7803(3) 0.90898(16) 0.0171(6) Uani 1 1 d . . . . . C16 C 0.23541(19) 0.7506(3) 0.83296(16) 0.0153(5) Uani 1 1 d . . . . . C17 C 0.2968(2) 0.6649(4) 0.97320(17) 0.0207(6) Uani 1 1 d . . . . . C18 C -0.0130(2) 0.7040(3) 0.90253(16) 0.0174(6) Uani 1 1 d . . . . . C19 C 0.0812(2) 0.1921(3) 1.15592(16) 0.0170(6) Uani 1 1 d . . . . . C20 C 0.0562(2) 0.3879(4) 0.70785(19) 0.0226(7) Uani 1 1 d . . . . . H20 H -0.001023 0.371203 0.706551 0.027 Uiso 1 1 calc R . . . . C21 C 0.1149(2) 0.4910(4) 0.76094(18) 0.0230(7) Uani 1 1 d . . . . . H21 H 0.097343 0.544660 0.794627 0.028 Uiso 1 1 calc R . . . . C22 C 0.2003(2) 0.5126(3) 0.76288(16) 0.0170(6) Uani 1 1 d . . . . . C23 C 0.2276(2) 0.0678(3) 1.21325(18) 0.0191(6) Uani 1 1 d . . . . . H23 H 0.286026 0.054496 1.216707 0.023 Uiso 1 1 calc R . . . . C24 C 0.1677(2) 0.1683(3) 1.15844(16) 0.0162(6) Uani 1 1 d . . . . . C25 C 0.1962(2) 0.2373(3) 1.09983(18) 0.0194(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 Sm1 0.01618(11) 0.01460(10) 0.01210(10) 0.00127(5) 0.00612(7) 0.00018(5) N1 0.0243(16) 0.0417(17) 0.0241(15) 0.0038(12) 0.0108(13) 0.0021(13) N2 0.0254(16) 0.046(2) 0.0213(14) 0.0060(13) 0.0056(12) 0.0055(14) O1 0.0258(13) 0.0385(14) 0.0171(11) -0.0049(10) 0.0086(10) -0.0054(11) O2 0.0292(13) 0.0328(13) 0.0213(11) -0.0052(10) 0.0134(10) -0.0093(11) O3 0.0183(11) 0.0185(11) 0.0173(11) -0.0075(8) 0.0038(9) 0.0008(8) O4 0.0343(17) 0.061(2) 0.0243(13) 0.0139(11) 0.0158(13) 0.0231(12) O5 0.0233(12) 0.0393(14) 0.0176(11) 0.0070(10) 0.0106(10) -0.0009(11) O6 0.0199(11) 0.0207(11) 0.0180(10) 0.0061(9) 0.0067(9) 0.0007(9) O7 0.0229(12) 0.0324(13) 0.0228(11) 0.0085(10) 0.0113(10) 0.0057(10) O8 0.0188(11) 0.0209(11) 0.0262(12) 0.0069(9) 0.0074(10) -0.0009(9) O9 0.0669(19) 0.0217(13) 0.0334(14) 0.0042(10) 0.0365(14) 0.0075(13) O1W 0.0516(17) 0.0206(12) 0.0394(15) -0.0048(11) 0.0225(13) -0.0057(12) O2W 0.0560(18) 0.0245(12) 0.0293(14) -0.0002(10) 0.0265(14) 0.0004(12) C1 0.0274(19) 0.050(2) 0.0249(18) 0.0021(16) 0.0122(16) 0.0040(17) C2 0.049(3) 0.142(6) 0.042(3) -0.042(3) 0.031(3) -0.040(3) C3 0.059(4) 0.160(7) 0.051(3) -0.045(3) 0.042(3) -0.052(4) C4 0.033(2) 0.068(3) 0.0226(19) -0.0021(19) 0.0135(17) 0.003(2) C5 0.031(2) 0.078(3) 0.0225(19) 0.002(2) 0.0062(17) -0.008(2) C6 0.033(2) 0.079(3) 0.027(2) -0.001(2) 0.0133(17) -0.010(2) C7 0.0213(17) 0.039(2) 0.0267(18) 0.0035(15) 0.0091(15) 0.0016(15) C8 0.0261(19) 0.042(2) 0.0265(19) -0.0003(14) 0.0110(16) 0.0041(15) C9 0.0209(17) 0.049(2) 0.0269(18) 0.0031(16) 0.0066(14) 0.0048(16) C10 0.0306(17) 0.0167(15) 0.0170(15) -0.0042(11) 0.0120(14) -0.0035(13) C11 0.0251(16) 0.0195(15) 0.0141(14) -0.0006(12) 0.0100(13) 0.0001(13) C12 0.044(2) 0.0192(16) 0.0269(17) 0.0039(13) 0.0178(16) 0.0088(15) C13 0.050(2) 0.0206(17) 0.0335(19) -0.0035(14) 0.0243(18) 0.0065(16) C14 0.0316(19) 0.0249(17) 0.0184(16) -0.0047(12) 0.0137(15) -0.0013(13) C15 0.0187(14) 0.0192(15) 0.0148(13) -0.0021(11) 0.0083(12) -0.0034(11) C16 0.0156(13) 0.0153(14) 0.0160(13) -0.0033(11) 0.0074(11) 0.0000(11) C17 0.0242(16) 0.0230(16) 0.0156(14) -0.0009(12) 0.0090(13) -0.0018(13) C18 0.0216(15) 0.0160(14) 0.0127(13) 0.0000(10) 0.0052(12) 0.0002(12) C19 0.0213(15) 0.0138(13) 0.0152(13) 0.0010(11) 0.0070(12) 0.0011(11) C20 0.0201(16) 0.0260(17) 0.0244(17) -0.0052(12) 0.0121(14) -0.0022(13) C21 0.0302(17) 0.0230(16) 0.0203(15) -0.0097(12) 0.0150(14) -0.0032(14) C22 0.0204(15) 0.0149(14) 0.0135(13) -0.0022(10) 0.0049(12) -0.0006(12) C23 0.0180(15) 0.0183(15) 0.0217(16) 0.0045(11) 0.0090(13) 0.0031(12) C24 0.0212(15) 0.0129(13) 0.0154(13) 0.0016(10) 0.0085(12) 0.0008(11) C25 0.0189(14) 0.0157(14) 0.0254(15) 0.0075(12) 0.0110(13) 0.0058(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' 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' Sm Sm -0.1638 3.4418 '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 Sm1 O2 51.73(8) . . ? O1 Sm1 O6 84.64(8) . . ? O1 Sm1 O6 69.34(8) . 3_567 ? O1 Sm1 O7 129.78(8) . . ? O1 Sm1 O1W 71.77(9) . . ? O1 Sm1 O2W 138.46(9) . . ? O5 Sm1 O1 130.17(8) . . ? O5 Sm1 O2 78.88(8) . . ? O5 Sm1 O6 146.15(8) . 3_567 ? O5 Sm1 O6 132.60(7) . . ? O5 Sm1 O7 80.83(8) . . ? O5 Sm1 O8 82.82(8) . . ? O5 Sm1 O1W 89.04(9) . . ? O5 Sm1 O2W 85.55(9) . . ? O6 Sm1 O2 129.76(7) . . ? O6 Sm1 O2 109.35(7) 3_567 . ? O6 Sm1 O6 67.90(8) . 3_567 ? O6 Sm1 O1W 70.93(9) . . ? O7 Sm1 O2 137.62(9) . . ? O7 Sm1 O6 52.25(7) . . ? O7 Sm1 O6 108.23(7) . 3_567 ? O7 Sm1 O1W 70.55(8) . . ? O7 Sm1 O2W 67.75(8) . . ? O8 Sm1 O1 87.31(8) . . ? O8 Sm1 O2 72.13(8) . . ? O8 Sm1 O6 136.88(7) . . ? O8 Sm1 O6 69.62(7) . 3_567 ? O8 Sm1 O7 140.85(8) . . ? O8 Sm1 O1W 144.40(8) . . ? O8 Sm1 O2W 75.72(8) . . ? O1W Sm1 O2 72.30(8) . . ? O1W Sm1 O6 124.80(8) . 3_567 ? O2W Sm1 O2 145.66(9) . . ? O2W Sm1 O6 82.78(9) . . ? O2W Sm1 O6 69.23(8) . 3_567 ? O2W Sm1 O1W 138.29(8) . . ? C7 N1 C1 126.5(3) . . ? C9 N1 C1 124.8(3) . . ? C9 N1 C7 108.3(3) . . ? C8 N2 H2 125.0 . . ? C9 N2 H2 125.0 . . ? C9 N2 C8 109.9(3) . . ? C10 O1 Sm1 95.64(18) . . ? C10 O2 Sm1 88.59(18) . . ? C22 O3 C16 117.8(2) . . ? C17 O5 Sm1 142.3(2) . . ? Sm1 O6 Sm1 112.11(8) . 3_567 ? C18 O6 Sm1 139.25(19) . 3_567 ? C18 O6 Sm1 91.38(18) . . ? C18 O7 Sm1 93.59(17) . . ? C25 O8 Sm1 122.8(2) . . ? Sm1 O1W H1WA 117.8 . . ? Sm1 O1W H1WB 134.5 . . ? H1WA O1W H1WB 107.7 . . ? Sm1 O2W H2WA 108.5 . . ? Sm1 O2W H2WB 106.1 . . ? H2WA O2W H2WB 106.4 . . ? C2 C1 N1 120.0(4) . . ? C2 C1 C6 119.8(4) . . ? C6 C1 N1 120.2(3) . . ? C1 C2 H2A 120.5 . . ? C1 C2 C3 119.0(4) . . ? C3 C2 H2A 120.5 . . ? C2 C3 H3 118.9 . . ? C4 C3 C2 122.2(4) . . ? C4 C3 H3 118.9 . . ? C3 C4 C4 122.2(5) . 3_666 ? C3 C4 C5 117.1(4) . . ? C5 C4 C4 120.6(5) . 3_666 ? C4 C5 H5 119.3 . . ? C4 C5 C6 121.4(4) . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 120.3(4) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? N1 C7 H7 126.7 . . ? C8 C7 N1 106.7(3) . . ? C8 C7 H7 126.7 . . ? N2 C8 H8 126.5 . . ? C7 C8 N2 107.0(3) . . ? C7 C8 H8 126.5 . . ? N1 C9 H9 126.0 . . ? N2 C9 N1 108.0(3) . . ? N2 C9 H9 126.0 . . ? O1 C10 C11 117.7(3) . 4_576 ? O2 C10 O1 121.6(3) . . ? O2 C10 C11 120.5(3) . 4_576 ? C12 C11 C10 116.5(3) . 4_575 ? C16 C11 C10 124.7(3) . 4_575 ? C16 C11 C12 118.7(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.6 . . ? C12 C13 H13 120.2 . . ? C12 C13 C14 119.7(3) . . ? C14 C13 H13 120.2 . . ? C13 C14 H14 119.4 . . ? C13 C14 C15 121.2(3) . . ? C15 C14 H14 119.4 . . ? C14 C15 C16 118.9(3) . . ? C14 C15 C17 117.9(3) . . ? C16 C15 C17 123.2(3) . . ? O3 C16 C11 120.1(2) . . ? O3 C16 C15 119.2(3) . . ? C15 C16 C11 120.7(3) . . ? O4 C17 O5 124.0(3) . . ? O4 C17 C15 119.2(3) . . ? O5 C17 C15 116.8(3) . . ? O6 C18 C19 120.3(3) . 3_567 ? O7 C18 O6 120.7(3) . . ? O7 C18 C19 118.9(3) . 3_567 ? C20 C19 C18 118.7(3) 4_566 3_567 ? C24 C19 C18 122.0(3) . 3_567 ? C24 C19 C20 119.3(3) . 4_566 ? C19 C20 H20 119.3 4_565 . ? C21 C20 C19 121.3(3) . 4_565 ? C21 C20 H20 119.3 . . ? C20 C21 H21 120.7 . . ? C20 C21 C22 118.6(3) . . ? C22 C21 H21 120.7 . . ? O3 C22 C23 115.5(3) . 4_565 ? C21 C22 O3 123.2(3) . . ? C21 C22 C23 121.3(3) . 4_565 ? C22 C23 H23 119.9 4_566 . ? C22 C23 C24 120.1(3) 4_566 . ? C24 C23 H23 119.9 . . ? C19 C24 C25 122.3(3) . . ? C23 C24 C19 119.3(3) . . ? C23 C24 C25 118.2(3) . . ? O8 C25 C24 118.3(3) . . ? O9 C25 O8 125.2(3) . . ? O9 C25 C24 116.5(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 Sm1 O1 2.450(2) . ? Sm1 O2 2.604(2) . ? Sm1 O5 2.316(2) . ? Sm1 O6 2.586(2) 3_567 ? Sm1 O6 2.515(2) . ? Sm1 O7 2.484(2) . ? Sm1 O8 2.373(2) . ? Sm1 O1W 2.533(3) . ? Sm1 O2W 2.510(2) . ? N1 C1 1.439(4) . ? N1 C7 1.380(5) . ? N1 C9 1.347(4) . ? N2 H2 0.8600 . ? N2 C8 1.366(5) . ? N2 C9 1.312(5) . ? O1 C10 1.267(4) . ? O2 C10 1.264(4) . ? O3 C16 1.387(3) . ? O3 C22 1.386(3) . ? O4 C17 1.242(4) . ? O5 C17 1.271(4) . ? O6 C18 1.282(3) . ? O7 C18 1.252(4) . ? O8 C25 1.264(4) . ? O9 C25 1.249(4) . ? O1W H1WA 0.8502 . ? O1W H1WB 0.8499 . ? O2W H2WA 0.8622 . ? O2W H2WB 0.8519 . ? C1 C2 1.365(6) . ? C1 C6 1.373(5) . ? C2 H2A 0.9300 . ? C2 C3 1.402(7) . ? C3 H3 0.9300 . ? C3 C4 1.371(6) . ? C4 C4 1.511(7) 3_666 ? C4 C5 1.382(6) . ? C5 H5 0.9300 . ? C5 C6 1.383(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C7 C8 1.356(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.499(4) 4_576 ? C11 C12 1.401(5) . ? C11 C16 1.397(4) . ? C12 H12 0.9300 . ? C12 C13 1.380(5) . ? C13 H13 0.9300 . ? C13 C14 1.382(5) . ? C14 H14 0.9300 . ? C14 C15 1.388(4) . ? C15 C16 1.396(4) . ? C15 C17 1.510(4) . ? C18 C19 1.496(4) 3_567 ? C19 C20 1.402(4) 4_566 ? C19 C24 1.400(4) . ? C20 H20 0.9300 . ? C20 C21 1.383(5) . ? C21 H21 0.9300 . ? C21 C22 1.384(4) . ? C22 C23 1.390(4) 4_565 ? C23 H23 0.9300 . ? C23 C24 1.391(4) . ? C24 C25 1.505(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 H1WB O9 0.85 1.94 2.744(4) 158.0 1_565 yes O2W H2WA O1 0.86 2.32 3.032(4) 140.1 3_567 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 Sm1 O1 C10 O2 16.5(3) . . . . ? Sm1 O1 C10 C11 -158.4(2) . . . 4_576 ? Sm1 O2 C10 O1 -15.5(3) . . . . ? Sm1 O2 C10 C11 159.3(3) . . . 4_576 ? Sm1 O5 C17 O4 -121.8(4) . . . . ? Sm1 O5 C17 C15 60.7(5) . . . . ? Sm1 O6 C18 O7 -112.5(3) 3_567 . . . ? Sm1 O6 C18 O7 14.7(3) . . . . ? Sm1 O6 C18 C19 71.3(4) 3_567 . . 3_567 ? Sm1 O6 C18 C19 -161.5(2) . . . 3_567 ? Sm1 O7 C18 O6 -14.9(3) . . . . ? Sm1 O7 C18 C19 161.3(2) . . . 3_567 ? Sm1 O8 C25 O9 79.0(4) . . . . ? Sm1 O8 C25 C24 -103.3(3) . . . . ? N1 C1 C2 C3 -178.4(5) . . . . ? N1 C1 C6 C5 178.3(4) . . . . ? N1 C7 C8 N2 -0.7(4) . . . . ? C1 N1 C7 C8 -172.5(4) . . . . ? C1 N1 C9 N2 173.2(3) . . . . ? C1 C2 C3 C4 -0.9(10) . . . . ? C2 C1 C6 C5 0.3(8) . . . . ? C2 C3 C4 C4 179.9(6) . . . 3_666 ? C2 C3 C4 C5 2.2(9) . . . . ? C3 C4 C5 C6 -2.3(8) . . . . ? C4 C4 C5 C6 180.0(5) 3_666 . . . ? C4 C5 C6 C1 1.1(8) . . . . ? C6 C1 C2 C3 -0.4(8) . . . . ? C7 N1 C1 C2 -134.4(5) . . . . ? C7 N1 C1 C6 47.6(6) . . . . ? C7 N1 C9 N2 0.2(5) . . . . ? C8 N2 C9 N1 -0.7(5) . . . . ? C9 N1 C1 C2 53.9(6) . . . . ? C9 N1 C1 C6 -124.1(5) . . . . ? C9 N1 C7 C8 0.3(4) . . . . ? C9 N2 C8 C7 0.9(4) . . . . ? C10 C11 C12 C13 -177.9(3) 4_575 . . . ? C10 C11 C16 O3 -0.7(5) 4_575 . . . ? C10 C11 C16 C15 179.2(3) 4_575 . . . ? C11 C12 C13 C14 -1.3(6) . . . . ? C12 C11 C16 O3 -178.2(3) . . . . ? C12 C11 C16 C15 1.8(5) . . . . ? C12 C13 C14 C15 1.3(6) . . . . ? C13 C14 C15 C16 0.2(5) . . . . ? C13 C14 C15 C17 -179.8(3) . . . . ? C14 C15 C16 O3 178.2(3) . . . . ? C14 C15 C16 C11 -1.8(4) . . . . ? C14 C15 C17 O4 -137.4(3) . . . . ? C14 C15 C17 O5 40.2(4) . . . . ? C16 O3 C22 C21 -38.5(4) . . . . ? C16 O3 C22 C23 143.4(3) . . . 4_565 ? C16 C11 C12 C13 -0.2(5) . . . . ? C16 C15 C17 O4 42.6(4) . . . . ? C16 C15 C17 O5 -139.8(3) . . . . ? C17 C15 C16 O3 -1.8(4) . . . . ? C17 C15 C16 C11 178.2(3) . . . . ? C18 C19 C24 C23 -178.8(3) 3_567 . . . ? C18 C19 C24 C25 -3.8(4) 3_567 . . . ? C19 C20 C21 C22 -1.0(5) 4_565 . . . ? C19 C24 C25 O8 83.0(4) . . . . ? C19 C24 C25 O9 -99.1(4) . . . . ? C20 C19 C24 C23 -1.1(4) 4_566 . . . ? C20 C19 C24 C25 173.8(3) 4_566 . . . ? C20 C21 C22 O3 -178.5(3) . . . . ? C20 C21 C22 C23 -0.5(5) . . . 4_565 ? C22 O3 C16 C11 -59.8(4) . . . . ? C22 O3 C16 C15 120.2(3) . . . . ? C22 C23 C24 C19 2.6(5) 4_566 . . . ? C22 C23 C24 C25 -172.6(3) 4_566 . . . ? C23 C24 C25 O8 -102.0(3) . . . . ? C23 C24 C25 O9 75.9(4) . . . . ?