# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_z1 _database_code_depnum_ccdc_archive 'CCDC 915817' #TrackingRef 'CCDC-915817.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H30.67 Ce N2 Na0.33 O8, 2(H2 O)' _chemical_formula_sum 'C50 H34.67 Ce N2 Na0.33 O10' _chemical_formula_weight 971.24 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' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 29.5404(12) _cell_length_b 29.5404(12) _cell_length_c 14.9218(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 11276.8(11) _cell_formula_units_Z 9 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2713 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 20.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4425 _exptl_absorpt_coefficient_mu 0.966 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6815 _exptl_absorpt_correction_T_max 0.7411 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 20850 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4907 _reflns_number_gt 4184 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction SAINT-Plus _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+51.6133P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4907 _refine_ls_number_parameters 303 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.73555(13) 0.30546(13) 0.9746(2) 0.0307(7) Uani 1 1 d . . . C2 C 0.77131(13) 0.29326(14) 0.9220(2) 0.0331(7) Uani 1 1 d . . . C3 C 0.79637(17) 0.32250(16) 0.8484(3) 0.0514(11) Uani 1 1 d . . . H3 H 0.7929 0.3513 0.8342 0.062 Uiso 1 1 calc R . . C4 C 0.82676(19) 0.31025(18) 0.7944(3) 0.0587(13) Uani 1 1 d . . . H4 H 0.8438 0.3312 0.7452 0.070 Uiso 1 1 calc R . . C5 C 0.83207(15) 0.26716(16) 0.8129(3) 0.0410(8) Uani 1 1 d . . . C6 C 0.80687(19) 0.23770(18) 0.8884(3) 0.0556(11) Uani 1 1 d . . . H6 H 0.8101 0.2088 0.9027 0.067 Uiso 1 1 calc R . . C7 C 0.77694(18) 0.25079(18) 0.9429(3) 0.0512(10) Uani 1 1 d . . . H7 H 0.7607 0.2309 0.9936 0.061 Uiso 1 1 calc R . . C8 C 0.86162(16) 0.25135(16) 0.7522(3) 0.0432(9) Uani 1 1 d . . . C9 C 0.87151(17) 0.26766(18) 0.6646(3) 0.0509(10) Uani 1 1 d . . . H9 H 0.8607 0.2902 0.6427 0.061 Uiso 1 1 calc R . . C10 C 0.89754(19) 0.25081(19) 0.6085(3) 0.0560(11) Uani 1 1 d . A . C11 C 0.91324(19) 0.21769(19) 0.6455(3) 0.0552(11) Uani 1 1 d . . . H11 H 0.9312 0.2057 0.6106 0.066 Uiso 1 1 calc R . . C12 C 0.90216(17) 0.20266(17) 0.7340(3) 0.0475(10) Uani 1 1 d . . . C13 C 0.9095(2) 0.2688(2) 0.5141(3) 0.0816(17) Uani 1 1 d DU . . C14 C 0.9616(3) 0.2894(4) 0.4847(6) 0.092(3) Uani 0.597(7) 1 d PDU A 1 H14 H 0.9860 0.2878 0.5221 0.110 Uiso 0.597(7) 1 calc PR A 1 C15 C 0.9769(5) 0.3121(5) 0.4003(7) 0.123(4) Uani 0.597(7) 1 d PDU A 1 H15 H 1.0112 0.3255 0.3810 0.147 Uiso 0.597(7) 1 calc PR A 1 C16 C 0.9407(5) 0.3145(5) 0.3457(8) 0.125(4) Uani 0.597(7) 1 d PDU A 1 H16 H 0.9506 0.3299 0.2894 0.150 Uiso 0.597(7) 1 calc PR A 1 C17 C 0.8882(6) 0.2935(5) 0.3751(8) 0.168(5) Uani 0.597(7) 1 d PDU A 1 H17 H 0.8641 0.2951 0.3370 0.201 Uiso 0.597(7) 1 calc PR A 1 C18 C 0.8713(4) 0.2702(4) 0.4601(7) 0.095(3) Uani 0.597(7) 1 d PDU A 1 H18 H 0.8370 0.2566 0.4792 0.114 Uiso 0.597(7) 1 calc PR A 1 C14' C 0.9371(5) 0.2544(5) 0.4567(8) 0.092(3) Uani 0.403(7) 1 d PD A 2 H14' H 0.9550 0.2389 0.4807 0.110 Uiso 0.403(7) 1 calc PR A 2 C15' C 0.9389(7) 0.2624(7) 0.3647(9) 0.123(4) Uani 0.403(7) 1 d PD A 2 H15' H 0.9580 0.2522 0.3289 0.147 Uiso 0.403(7) 1 calc PR A 2 C16' C 0.9129(7) 0.2853(7) 0.3254(11) 0.125(4) Uani 0.403(7) 1 d PD A 2 H16' H 0.9139 0.2906 0.2638 0.150 Uiso 0.403(7) 1 calc PR A 2 C17' C 0.8846(8) 0.3004(8) 0.3826(11) 0.168(5) Uani 0.403(7) 1 d PD A 2 H17' H 0.8668 0.3160 0.3583 0.201 Uiso 0.403(7) 1 calc PR A 2 C18' C 0.8830(6) 0.2923(6) 0.4753(11) 0.095(3) Uani 0.403(7) 1 d PD A 2 H18' H 0.8642 0.3025 0.5116 0.114 Uiso 0.403(7) 1 calc PR A 2 C19 C 0.91753(18) 0.16695(17) 0.7769(3) 0.0489(10) Uani 1 1 d . . . C20 C 0.92276(17) 0.12994(17) 0.7276(3) 0.0467(10) Uani 1 1 d . . . H20 H 0.9177 0.1280 0.6659 0.056 Uiso 1 1 calc R . . C21 C 0.93538(16) 0.09602(16) 0.7694(3) 0.0423(9) Uani 1 1 d . . . H21 H 0.9381 0.0710 0.7357 0.051 Uiso 1 1 calc R . . C22 C 0.94400(17) 0.09894(17) 0.8606(3) 0.0458(10) Uani 1 1 d . . . C23 C 0.9390(3) 0.1359(2) 0.9099(3) 0.0751(17) Uani 1 1 d . . . H23 H 0.9446 0.1382 0.9715 0.090 Uiso 1 1 calc R . . C24 C 0.9256(3) 0.1692(2) 0.8678(3) 0.0752(17) Uani 1 1 d . . . H24 H 0.9220 0.1936 0.9017 0.090 Uiso 1 1 calc R . . C25 C 0.95951(17) 0.06422(16) 0.9070(3) 0.0446(9) Uani 1 1 d . . . Ce1 Ce 1.0000 0.0000 1.0000 0.02150(12) Uani 1 6 d S . . Ce2 Ce 1.0000 0.0000 0.739197(19) 0.02308(11) Uani 1 3 d S . . Na1 Na 0.6667 0.3333 0.8333 0.0277(6) Uani 1 6 d S . . N1 N 0.87691(14) 0.21941(14) 0.7868(2) 0.0476(8) Uani 1 1 d . . . H1 H 0.8706 0.2098 0.8420 0.057 Uiso 1 1 calc R . . O1 O 0.71330(11) 0.28016(11) 1.04403(16) 0.0421(6) Uani 1 1 d . . . O2 O 0.72789(9) 0.34161(9) 0.94629(15) 0.0306(5) Uani 1 1 d . . . O3 O 0.96023(19) 0.06325(16) 0.9905(2) 0.0824(12) Uani 1 1 d U . . O4 O 0.96994(9) 0.03437(9) 0.86141(16) 0.0343(5) Uani 1 1 d . . . O1W O 0.9382(4) 0.1045(4) 0.1444(4) 0.245(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 C1 0.0293(16) 0.0364(17) 0.0301(17) -0.0062(14) -0.0056(13) 0.0191(15) C2 0.0340(17) 0.0385(18) 0.0329(17) -0.0021(14) -0.0020(14) 0.0227(15) C3 0.066(3) 0.048(2) 0.062(3) 0.019(2) 0.027(2) 0.046(2) C4 0.078(3) 0.061(3) 0.063(3) 0.028(2) 0.036(2) 0.055(3) C5 0.049(2) 0.050(2) 0.039(2) 0.0030(17) 0.0024(17) 0.0365(19) C6 0.081(3) 0.066(3) 0.053(2) 0.014(2) 0.014(2) 0.062(3) C7 0.070(3) 0.066(3) 0.042(2) 0.014(2) 0.013(2) 0.052(2) C8 0.051(2) 0.050(2) 0.046(2) 0.0028(18) 0.0017(18) 0.039(2) C9 0.062(3) 0.065(3) 0.052(2) 0.014(2) 0.012(2) 0.052(2) C10 0.070(3) 0.073(3) 0.052(2) 0.014(2) 0.014(2) 0.056(3) C11 0.076(3) 0.076(3) 0.047(2) 0.008(2) 0.012(2) 0.063(3) C12 0.065(3) 0.059(2) 0.044(2) 0.0021(19) 0.0030(19) 0.050(2) C13 0.111(4) 0.118(4) 0.064(3) 0.032(3) 0.028(3) 0.093(4) C14 0.116(7) 0.119(7) 0.082(5) 0.029(5) 0.042(5) 0.089(6) C15 0.127(8) 0.163(9) 0.115(7) 0.036(6) 0.058(6) 0.100(7) C16 0.128(9) 0.160(10) 0.097(6) 0.042(7) 0.034(6) 0.081(8) C17 0.204(8) 0.218(9) 0.123(7) 0.066(6) 0.023(6) 0.137(7) C18 0.128(6) 0.112(8) 0.075(5) 0.018(6) 0.007(5) 0.082(6) C14' 0.116(7) 0.119(7) 0.082(5) 0.029(5) 0.042(5) 0.089(6) C15' 0.127(8) 0.163(9) 0.115(7) 0.036(6) 0.058(6) 0.100(7) C16' 0.128(9) 0.160(10) 0.097(6) 0.042(7) 0.034(6) 0.081(8) C17' 0.204(8) 0.218(9) 0.123(7) 0.066(6) 0.023(6) 0.137(7) C18' 0.128(6) 0.112(8) 0.075(5) 0.018(6) 0.007(5) 0.082(6) C19 0.070(3) 0.060(3) 0.043(2) 0.0009(19) -0.0005(19) 0.052(2) C20 0.065(3) 0.069(3) 0.0324(19) -0.0025(18) -0.0012(18) 0.053(2) C21 0.056(2) 0.055(2) 0.0388(19) -0.0057(17) -0.0015(17) 0.045(2) C22 0.067(3) 0.057(2) 0.037(2) -0.0078(18) -0.0081(18) 0.049(2) C23 0.142(5) 0.096(4) 0.039(2) -0.016(2) -0.019(3) 0.098(4) C24 0.146(5) 0.089(4) 0.046(3) -0.016(2) -0.015(3) 0.101(4) C25 0.066(3) 0.054(2) 0.0341(19) -0.0081(17) -0.0097(18) 0.046(2) Ce1 0.02316(15) 0.02316(15) 0.0182(2) 0.000 0.000 0.01158(8) Ce2 0.02490(13) 0.02490(13) 0.01945(17) 0.000 0.000 0.01245(7) Na1 0.0297(10) 0.0297(10) 0.0239(15) 0.000 0.000 0.0148(5) N1 0.068(2) 0.060(2) 0.0389(17) 0.0037(15) 0.0050(16) 0.0504(19) O1 0.0584(16) 0.0528(16) 0.0314(13) 0.0103(11) 0.0096(12) 0.0399(14) O2 0.0299(11) 0.0358(12) 0.0321(12) 0.0015(10) 0.0020(10) 0.0209(10) O3 0.154(4) 0.105(3) 0.0452(18) -0.0148(18) -0.023(2) 0.108(3) O4 0.0424(14) 0.0410(13) 0.0325(12) 0.0011(10) 0.0028(10) 0.0306(12) O1W 0.512(16) 0.392(12) 0.073(4) 0.055(5) 0.058(6) 0.409(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 O1 1.255(4) . ? C1 O2 1.269(4) . ? C1 C2 1.497(4) . ? C1 Ce2 2.938(3) 4_455 ? C2 C3 1.365(5) . ? C2 C7 1.381(5) . ? C3 C4 1.382(5) . ? C3 H3 0.9300 . ? C4 C5 1.386(5) . ? C4 H4 0.9300 . ? C5 C6 1.391(6) . ? C5 C8 1.485(5) . ? C6 C7 1.391(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N1 1.337(5) . ? C8 C9 1.374(6) . ? C9 C10 1.387(6) . ? C9 H9 0.9300 . ? C10 C11 1.389(6) . ? C10 C13 1.485(6) . ? C11 C12 1.380(6) . ? C11 H11 0.9300 . ? C12 N1 1.339(5) . ? C12 C19 1.485(5) . ? C13 C14' 1.388(8) . ? C13 C18' 1.401(9) . ? C13 C18 1.403(8) . ? C13 C14 1.414(8) . ? C14 C15 1.391(8) . ? C14 H14 0.9300 . ? C15 C16 1.372(9) . ? C15 H15 0.9300 . ? C16 C17 1.423(9) . ? C16 H16 0.9300 . ? C17 C18 1.409(9) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C14' C15' 1.389(9) . ? C14' H14' 0.9300 . ? C15' C16' 1.384(10) . ? C15' H15' 0.9300 . ? C16' C17' 1.412(10) . ? C16' H16' 0.9300 . ? C17' C18' 1.401(10) . ? C17' H17' 0.9300 . ? C18' H18' 0.9300 . ? C19 C24 1.374(6) . ? C19 C20 1.389(5) . ? C20 C21 1.380(5) . ? C20 H20 0.9300 . ? C21 C22 1.379(5) . ? C21 H21 0.9300 . ? C22 C23 1.385(6) . ? C22 C25 1.487(5) . ? C23 C24 1.382(6) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 O3 1.248(5) . ? C25 O4 1.268(4) . ? Ce1 O4 2.645(2) 2_645 ? Ce1 O4 2.645(2) 11_667 ? Ce1 O4 2.645(2) 3_765 ? Ce1 O4 2.645(2) . ? Ce1 O4 2.645(2) 12_547 ? Ce1 O4 2.645(2) 10_757 ? Ce1 O3 2.662(3) 2_645 ? Ce1 O3 2.662(3) 11_667 ? Ce1 O3 2.662(3) 10_757 ? Ce1 O3 2.662(3) 3_765 ? Ce1 O3 2.662(3) 12_547 ? Ce1 O3 2.662(3) . ? Ce2 O4 2.459(2) 3_765 ? Ce2 O4 2.459(2) . ? Ce2 O4 2.459(2) 2_645 ? Ce2 O2 2.537(2) 8_644 ? Ce2 O2 2.537(2) 9_654 ? Ce2 O2 2.537(2) 7_544 ? Ce2 O1 2.590(2) 9_654 ? Ce2 O1 2.590(2) 8_644 ? Ce2 O1 2.591(2) 7_544 ? Na1 O2 2.394(2) 16_656 ? Na1 O2 2.394(2) . ? Na1 O2 2.394(2) 3_665 ? Na1 O2 2.394(2) 18_546 ? Na1 O2 2.394(2) 2_655 ? Na1 O2 2.394(2) 17_556 ? N1 H1 0.8600 . ? O1 Ce2 2.591(2) 4_455 ? O2 Ce2 2.537(2) 4_455 ? 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 C1 O2 121.0(3) . . ? O1 C1 C2 120.8(3) . . ? O2 C1 C2 118.2(3) . . ? O1 C1 Ce2 61.70(17) . 4_455 ? O2 C1 Ce2 59.32(16) . 4_455 ? C2 C1 Ce2 177.5(2) . 4_455 ? C3 C2 C7 118.9(3) . . ? C3 C2 C1 119.6(3) . . ? C7 C2 C1 121.4(3) . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 120.8(4) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 117.7(3) . . ? C4 C5 C8 121.5(4) . . ? C6 C5 C8 120.8(3) . . ? C7 C6 C5 121.0(4) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C2 C7 C6 120.2(4) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? N1 C8 C9 121.8(3) . . ? N1 C8 C5 116.5(3) . . ? C9 C8 C5 121.7(3) . . ? C8 C9 C10 120.5(4) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C11 117.0(4) . . ? C9 C10 C13 121.3(4) . . ? C11 C10 C13 121.7(4) . . ? C12 C11 C10 119.9(4) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? N1 C12 C11 122.1(3) . . ? N1 C12 C19 115.7(3) . . ? C11 C12 C19 122.2(3) . . ? C14' C13 C18' 117.0(9) . . ? C14' C13 C18 104.9(8) . . ? C18' C13 C18 25.0(8) . . ? C14' C13 C14 42.2(6) . . ? C18' C13 C14 114.5(8) . . ? C18 C13 C14 121.8(7) . . ? C14' C13 C10 123.1(6) . . ? C18' C13 C10 118.6(8) . . ? C18 C13 C10 120.4(6) . . ? C14 C13 C10 117.5(5) . . ? C15 C14 C13 120.6(8) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 119.3(9) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 120.1(9) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 122.2(10) . . ? C18 C17 H17 118.9 . . ? C16 C17 H17 118.9 . . ? C13 C18 C17 116.0(9) . . ? C13 C18 H18 122.0 . . ? C17 C18 H18 122.0 . . ? C13 C14' C15' 122.5(10) . . ? C13 C14' H14' 118.8 . . ? C15' C14' H14' 118.8 . . ? C16' C15' C14' 121.2(11) . . ? C16' C15' H15' 119.4 . . ? C14' C15' H15' 119.4 . . ? C15' C16' C17' 117.3(11) . . ? C15' C16' H16' 121.3 . . ? C17' C16' H16' 121.3 . . ? C18' C17' C16' 121.1(12) . . ? C18' C17' H17' 119.5 . . ? C16' C17' H17' 119.5 . . ? C17' C18' C13 121.0(11) . . ? C17' C18' H18' 119.5 . . ? C13 C18' H18' 119.5 . . ? C24 C19 C20 118.5(4) . . ? C24 C19 C12 119.8(4) . . ? C20 C19 C12 121.7(4) . . ? C21 C20 C19 120.6(4) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 120.6(3) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 119.0(4) . . ? C21 C22 C25 121.8(3) . . ? C23 C22 C25 119.2(4) . . ? C24 C23 C22 120.1(4) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C19 C24 C23 121.2(4) . . ? C19 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? O3 C25 O4 120.5(3) . . ? O3 C25 C22 119.7(3) . . ? O4 C25 C22 119.8(3) . . ? O4 Ce1 O4 180.0 2_645 11_667 ? O4 Ce1 O4 65.37(8) 2_645 3_765 ? O4 Ce1 O4 114.63(8) 11_667 3_765 ? O4 Ce1 O4 65.37(8) 2_645 . ? O4 Ce1 O4 114.63(8) 11_667 . ? O4 Ce1 O4 65.37(8) 3_765 . ? O4 Ce1 O4 114.63(8) 2_645 12_547 ? O4 Ce1 O4 65.37(8) 11_667 12_547 ? O4 Ce1 O4 180.00(9) 3_765 12_547 ? O4 Ce1 O4 114.63(8) . 12_547 ? O4 Ce1 O4 114.63(8) 2_645 10_757 ? O4 Ce1 O4 65.37(8) 11_667 10_757 ? O4 Ce1 O4 114.63(8) 3_765 10_757 ? O4 Ce1 O4 180.00(6) . 10_757 ? O4 Ce1 O4 65.37(8) 12_547 10_757 ? O4 Ce1 O3 48.58(8) 2_645 2_645 ? O4 Ce1 O3 131.42(8) 11_667 2_645 ? O4 Ce1 O3 108.55(9) 3_765 2_645 ? O4 Ce1 O3 102.64(11) . 2_645 ? O4 Ce1 O3 71.45(9) 12_547 2_645 ? O4 Ce1 O3 77.36(11) 10_757 2_645 ? O4 Ce1 O3 131.42(8) 2_645 11_667 ? O4 Ce1 O3 48.58(8) 11_667 11_667 ? O4 Ce1 O3 71.45(9) 3_765 11_667 ? O4 Ce1 O3 77.36(11) . 11_667 ? O4 Ce1 O3 108.55(9) 12_547 11_667 ? O4 Ce1 O3 102.64(11) 10_757 11_667 ? O3 Ce1 O3 180.00(16) 2_645 11_667 ? O4 Ce1 O3 71.45(9) 2_645 10_757 ? O4 Ce1 O3 108.55(9) 11_667 10_757 ? O4 Ce1 O3 77.36(11) 3_765 10_757 ? O4 Ce1 O3 131.42(8) . 10_757 ? O4 Ce1 O3 102.64(11) 12_547 10_757 ? O4 Ce1 O3 48.58(8) 10_757 10_757 ? O3 Ce1 O3 60.280(13) 2_645 10_757 ? O3 Ce1 O3 119.720(14) 11_667 10_757 ? O4 Ce1 O3 102.64(11) 2_645 3_765 ? O4 Ce1 O3 77.36(11) 11_667 3_765 ? O4 Ce1 O3 48.58(8) 3_765 3_765 ? O4 Ce1 O3 108.55(9) . 3_765 ? O4 Ce1 O3 131.42(8) 12_547 3_765 ? O4 Ce1 O3 71.45(9) 10_757 3_765 ? O3 Ce1 O3 119.720(13) 2_645 3_765 ? O3 Ce1 O3 60.280(13) 11_667 3_765 ? O3 Ce1 O3 60.280(14) 10_757 3_765 ? O4 Ce1 O3 77.36(11) 2_645 12_547 ? O4 Ce1 O3 102.64(11) 11_667 12_547 ? O4 Ce1 O3 131.42(8) 3_765 12_547 ? O4 Ce1 O3 71.45(9) . 12_547 ? O4 Ce1 O3 48.58(8) 12_547 12_547 ? O4 Ce1 O3 108.55(9) 10_757 12_547 ? O3 Ce1 O3 60.280(14) 2_645 12_547 ? O3 Ce1 O3 119.720(13) 11_667 12_547 ? O3 Ce1 O3 119.720(14) 10_757 12_547 ? O3 Ce1 O3 180.0 3_765 12_547 ? O4 Ce1 O3 108.55(9) 2_645 . ? O4 Ce1 O3 71.45(9) 11_667 . ? O4 Ce1 O3 102.64(11) 3_765 . ? O4 Ce1 O3 48.58(8) . . ? O4 Ce1 O3 77.36(11) 12_547 . ? O4 Ce1 O3 131.42(8) 10_757 . ? O3 Ce1 O3 119.720(14) 2_645 . ? O3 Ce1 O3 60.280(13) 11_667 . ? O3 Ce1 O3 180.000(1) 10_757 . ? O3 Ce1 O3 119.720(14) 3_765 . ? O3 Ce1 O3 60.280(13) 12_547 . ? O4 Ce2 O4 71.03(8) 3_765 . ? O4 Ce2 O4 71.03(8) 3_765 2_645 ? O4 Ce2 O4 71.03(8) . 2_645 ? O4 Ce2 O2 128.59(8) 3_765 8_644 ? O4 Ce2 O2 97.48(7) . 8_644 ? O4 Ce2 O2 153.90(8) 2_645 8_644 ? O4 Ce2 O2 153.90(8) 3_765 9_654 ? O4 Ce2 O2 128.60(8) . 9_654 ? O4 Ce2 O2 97.48(7) 2_645 9_654 ? O2 Ce2 O2 70.92(8) 8_644 9_654 ? O4 Ce2 O2 97.47(7) 3_765 7_544 ? O4 Ce2 O2 153.90(8) . 7_544 ? O4 Ce2 O2 128.59(8) 2_645 7_544 ? O2 Ce2 O2 70.92(8) 8_644 7_544 ? O2 Ce2 O2 70.92(8) 9_654 7_544 ? O4 Ce2 O1 141.58(8) 3_765 9_654 ? O4 Ce2 O1 77.96(8) . 9_654 ? O4 Ce2 O1 77.90(8) 2_645 9_654 ? O2 Ce2 O1 76.77(8) 8_644 9_654 ? O2 Ce2 O1 50.72(7) 9_654 9_654 ? O2 Ce2 O1 119.76(7) 7_544 9_654 ? O4 Ce2 O1 77.96(8) 3_765 8_644 ? O4 Ce2 O1 77.91(8) . 8_644 ? O4 Ce2 O1 141.58(8) 2_645 8_644 ? O2 Ce2 O1 50.73(7) 8_644 8_644 ? O2 Ce2 O1 119.76(7) 9_654 8_644 ? O2 Ce2 O1 76.76(8) 7_544 8_644 ? O1 Ce2 O1 117.36(3) 9_654 8_644 ? O4 Ce2 O1 77.91(8) 3_765 7_544 ? O4 Ce2 O1 141.58(8) . 7_544 ? O4 Ce2 O1 77.96(8) 2_645 7_544 ? O2 Ce2 O1 119.76(7) 8_644 7_544 ? O2 Ce2 O1 76.76(8) 9_654 7_544 ? O2 Ce2 O1 50.72(7) 7_544 7_544 ? O1 Ce2 O1 117.36(3) 9_654 7_544 ? O1 Ce2 O1 117.36(3) 8_644 7_544 ? C1 Ce2 C1 97.38(8) 9_654 7_544 ? O2 Na1 O2 180.0 16_656 . ? O2 Na1 O2 104.11(8) 16_656 3_665 ? O2 Na1 O2 75.89(8) . 3_665 ? O2 Na1 O2 75.89(8) 16_656 18_546 ? O2 Na1 O2 104.11(8) . 18_546 ? O2 Na1 O2 180.00(7) 3_665 18_546 ? O2 Na1 O2 104.11(8) 16_656 2_655 ? O2 Na1 O2 75.89(8) . 2_655 ? O2 Na1 O2 75.89(8) 3_665 2_655 ? O2 Na1 O2 104.11(8) 18_546 2_655 ? O2 Na1 O2 75.89(8) 16_656 17_556 ? O2 Na1 O2 104.11(8) . 17_556 ? O2 Na1 O2 104.11(8) 3_665 17_556 ? O2 Na1 O2 75.89(8) 18_546 17_556 ? O2 Na1 O2 180.0 2_655 17_556 ? C8 N1 C12 118.8(3) . . ? C8 N1 H1 120.6 . . ? C12 N1 H1 120.6 . . ? C1 O1 Ce2 93.06(19) . 4_455 ? C1 O2 Na1 126.3(2) . . ? C1 O2 Ce2 95.20(19) . 4_455 ? Na1 O2 Ce2 92.70(7) . 4_455 ? C25 O3 Ce1 95.0(2) . . ? C25 O4 Ce2 161.6(3) . . ? C25 O4 Ce1 95.3(2) . . ? Ce2 O4 Ce1 99.30(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.255 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.083 data_Eu _database_code_depnum_ccdc_archive 'CCDC 915818' #TrackingRef 'Eu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H14 Eu N3 O7' _chemical_formula_sum 'C24 H14 Eu N3 O7' _chemical_formula_weight 608.34 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' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd _symmetry_space_group_name_Hall '-F 2uv 2vw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 22.264(12) _cell_length_b 28.623(16) _cell_length_c 29.104(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 18546(17) _cell_formula_units_Z 32 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1030 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 15.73 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.743 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 9536 _exptl_absorpt_coefficient_mu 2.756 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5458 _exptl_absorpt_correction_T_max 0.6368 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 22868 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4090 _reflns_number_gt 3329 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction SAINT-Plus _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+195.5178P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4090 _refine_ls_number_parameters 324 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7199(3) 0.0785(2) 0.7890(2) 0.0295(15) Uani 1 1 d . . . C2 C 0.7331(3) 0.1146(2) 0.8252(2) 0.0265(14) Uani 1 1 d . . . C3 C 0.7825(3) 0.1100(2) 0.8544(2) 0.0345(16) Uani 1 1 d . . . H3 H 0.8060 0.0832 0.8533 0.041 Uiso 1 1 calc R . . C4 C 0.7963(3) 0.1449(3) 0.8847(2) 0.0360(17) Uani 1 1 d . . . H4 H 0.8294 0.1416 0.9040 0.043 Uiso 1 1 calc R . . C5 C 0.7613(3) 0.1856(2) 0.8873(2) 0.0318(15) Uani 1 1 d . . . C6 C 0.7116(3) 0.1894(2) 0.8580(2) 0.0318(16) Uani 1 1 d . . . H6 H 0.6876 0.2159 0.8592 0.038 Uiso 1 1 calc R . . C7 C 0.6980(3) 0.1543(3) 0.8276(2) 0.0304(15) Uani 1 1 d . . . H7 H 0.6648 0.1574 0.8084 0.036 Uiso 1 1 calc R . . C8 C 0.7775(3) 0.2239(2) 0.9188(2) 0.0318(16) Uani 1 1 d . . . C9 C 1.0492(3) 0.2310(3) 1.0857(2) 0.0312(16) Uani 1 1 d . . . C10 C 0.9951(3) 0.2380(3) 1.0559(2) 0.0296(15) Uani 1 1 d . . . C11 C 0.9893(3) 0.2128(3) 1.0155(2) 0.0381(18) Uani 1 1 d . . . H11 H 1.0191 0.1917 1.0071 0.046 Uiso 1 1 calc R . . C12 C 0.9398(3) 0.2189(3) 0.9878(3) 0.0404(19) Uani 1 1 d . . . H12 H 0.9364 0.2020 0.9606 0.049 Uiso 1 1 calc R . . C13 C 0.8951(3) 0.2498(3) 1.0003(2) 0.0328(16) Uani 1 1 d . . . C14 C 0.9011(3) 0.2760(3) 1.0407(2) 0.0392(18) Uani 1 1 d . . . H14 H 0.8722 0.2980 1.0486 0.047 Uiso 1 1 calc R . . C15 C 0.9507(3) 0.2688(3) 1.0686(2) 0.0378(18) Uani 1 1 d . . . H15 H 0.9539 0.2849 1.0962 0.045 Uiso 1 1 calc R . . C16 C 0.8399(3) 0.2546(2) 0.9719(2) 0.0312(15) Uani 1 1 d . . . C17 C 0.5933(3) 0.4480(3) 0.9699(3) 0.0390(17) Uani 1 1 d . . . C18 C 0.6375(3) 0.4093(3) 0.9638(2) 0.0338(16) Uani 1 1 d . . . C19 C 0.6903(4) 0.4079(3) 0.9888(3) 0.054(2) Uani 1 1 d . . . H19 H 0.6996 0.4322 1.0087 0.065 Uiso 1 1 calc R . . C20 C 0.7293(4) 0.3708(3) 0.9846(3) 0.054(2) Uani 1 1 d . . . H20 H 0.7645 0.3703 1.0017 0.065 Uiso 1 1 calc R . . C21 C 0.7162(3) 0.3341(3) 0.9548(2) 0.0333(16) Uani 1 1 d . . . C22 C 0.6636(3) 0.3359(3) 0.9299(2) 0.0394(18) Uani 1 1 d . . . H22 H 0.6541 0.3117 0.9099 0.047 Uiso 1 1 calc R . . C23 C 0.6248(3) 0.3732(3) 0.9342(2) 0.0370(18) Uani 1 1 d . . . H23 H 0.5897 0.3739 0.9169 0.044 Uiso 1 1 calc R . . C24 C 0.7565(3) 0.2936(3) 0.9508(2) 0.0351(17) Uani 1 1 d . . . Eu1 Eu 1.195432(14) 0.221669(11) 1.047814(10) 0.02455(15) Uani 1 1 d D . . N1 N 0.7405(3) 0.2603(2) 0.9213(2) 0.0347(14) Uani 1 1 d . . . N2 N 0.8058(3) 0.2919(2) 0.9775(2) 0.0377(15) Uani 1 1 d . . . N3 N 0.8286(3) 0.2195(2) 0.94311(19) 0.0338(14) Uani 1 1 d . . . O1 O 0.6815(2) 0.08784(18) 0.75881(17) 0.0408(13) Uani 1 1 d . . . O2 O 0.7479(2) 0.04079(17) 0.78882(17) 0.0385(12) Uani 1 1 d . . . O3 O 1.0944(2) 0.2112(2) 1.06785(17) 0.0436(13) Uani 1 1 d . . . O4 O 1.0467(2) 0.2452(2) 1.12650(16) 0.0404(13) Uani 1 1 d . . . O5 O 0.6068(2) 0.48029(19) 0.99713(19) 0.0479(14) Uani 1 1 d . . . O6 O 0.5449(2) 0.4454(2) 0.94772(18) 0.0467(14) Uani 1 1 d . . . O1W O 1.1898(4) 0.1445(3) 1.0854(3) 0.093(3) Uani 1 1 d D . . H1W H 1.207(3) 0.1454(8) 1.1101(12) 0.06(4) Uiso 1 1 d D . . H2W H 1.202(4) 0.1243(3) 1.0677(10) 2(3) Uiso 1 1 d 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 C1 0.027(4) 0.024(4) 0.038(4) -0.008(3) 0.005(3) -0.004(3) C2 0.030(4) 0.022(4) 0.027(3) -0.004(3) 0.002(3) -0.003(3) C3 0.032(4) 0.027(4) 0.044(4) -0.010(3) -0.006(3) 0.011(3) C4 0.028(4) 0.032(4) 0.048(4) -0.009(3) -0.015(3) 0.009(3) C5 0.029(4) 0.030(4) 0.036(4) -0.009(3) -0.007(3) 0.003(3) C6 0.029(4) 0.030(4) 0.036(4) -0.012(3) -0.009(3) 0.012(3) C7 0.021(3) 0.038(4) 0.033(3) -0.009(3) -0.008(3) 0.001(3) C8 0.032(4) 0.028(4) 0.035(4) -0.006(3) -0.008(3) 0.006(3) C9 0.022(4) 0.047(5) 0.025(3) 0.006(3) -0.001(3) -0.001(3) C10 0.025(4) 0.038(4) 0.025(3) 0.002(3) -0.004(3) -0.001(3) C11 0.026(4) 0.051(5) 0.037(4) -0.010(3) -0.009(3) 0.011(3) C12 0.036(4) 0.050(5) 0.035(4) -0.016(3) -0.012(3) 0.012(4) C13 0.029(4) 0.036(4) 0.034(4) -0.003(3) -0.009(3) 0.003(3) C14 0.032(4) 0.046(5) 0.040(4) -0.019(3) -0.009(3) 0.011(3) C15 0.031(4) 0.051(5) 0.032(4) -0.015(3) -0.007(3) 0.002(3) C16 0.027(4) 0.031(4) 0.035(4) -0.009(3) -0.009(3) 0.006(3) C17 0.030(4) 0.041(5) 0.047(4) -0.006(4) 0.005(3) 0.007(3) C18 0.028(4) 0.035(4) 0.038(4) -0.007(3) -0.002(3) 0.010(3) C19 0.046(5) 0.044(5) 0.072(6) -0.032(4) -0.018(4) 0.016(4) C20 0.041(5) 0.056(6) 0.065(5) -0.030(4) -0.027(4) 0.021(4) C21 0.032(4) 0.032(4) 0.036(4) -0.014(3) -0.011(3) 0.009(3) C22 0.038(4) 0.040(5) 0.040(4) -0.012(3) -0.012(3) 0.009(4) C23 0.031(4) 0.038(5) 0.041(4) -0.008(3) -0.015(3) 0.012(3) C24 0.032(4) 0.033(4) 0.040(4) -0.013(3) -0.013(3) 0.004(3) Eu1 0.0241(2) 0.0227(2) 0.0269(2) -0.00135(12) 0.00280(12) 0.00174(13) N1 0.031(3) 0.034(4) 0.039(3) -0.016(3) -0.013(2) 0.011(3) N2 0.034(4) 0.031(3) 0.048(4) -0.015(3) -0.017(3) 0.011(3) N3 0.027(3) 0.038(4) 0.037(3) -0.013(3) -0.012(3) 0.008(3) O1 0.036(3) 0.041(3) 0.046(3) -0.019(2) -0.011(2) 0.006(2) O2 0.043(3) 0.025(3) 0.046(3) -0.007(2) 0.001(2) 0.005(2) O3 0.024(3) 0.072(4) 0.035(3) 0.000(3) -0.001(2) -0.002(3) O4 0.033(3) 0.064(4) 0.024(2) -0.003(2) -0.007(2) 0.008(2) O5 0.032(3) 0.047(3) 0.065(4) -0.024(3) -0.002(3) 0.010(2) O6 0.032(3) 0.060(4) 0.047(3) -0.014(3) -0.008(2) 0.019(3) O1W 0.106(7) 0.062(5) 0.111(7) 0.049(5) 0.011(5) -0.003(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 O2 1.246(8) . ? C1 O1 1.255(8) . ? C1 C2 1.503(9) . ? C1 Eu1 2.957(6) 16_446 ? C2 C7 1.382(10) . ? C2 C3 1.397(9) . ? C3 C4 1.366(10) . ? C3 H3 0.9300 . ? C4 C5 1.404(10) . ? C4 H4 0.9300 . ? C5 C6 1.400(9) . ? C5 C8 1.475(9) . ? C6 C7 1.372(9) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N1 1.332(9) . ? C8 N3 1.345(9) . ? C9 O4 1.257(8) . ? C9 O3 1.266(8) . ? C9 C10 1.498(9) . ? C10 C15 1.375(10) . ? C10 C11 1.384(10) . ? C11 C12 1.377(9) . ? C11 H11 0.9300 . ? C12 C13 1.380(10) . ? C12 H12 0.9300 . ? C13 C14 1.400(9) . ? C13 C16 1.489(9) . ? C14 C15 1.385(10) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 N2 1.319(9) . ? C16 N3 1.332(8) . ? C17 O5 1.255(9) . ? C17 O6 1.258(9) . ? C17 C18 1.492(10) . ? C18 C23 1.374(10) . ? C18 C19 1.385(10) . ? C19 C20 1.375(11) . ? C19 H19 0.9300 . ? C20 C21 1.392(10) . ? C20 H20 0.9300 . ? C21 C22 1.380(10) . ? C21 C24 1.470(10) . ? C22 C23 1.377(10) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 N1 1.331(8) . ? C24 N2 1.347(9) . ? Eu1 O4 2.310(5) 11_656 ? Eu1 O5 2.328(5) 2_655 ? Eu1 O6 2.343(5) 30_657 ? Eu1 O3 2.343(5) . ? Eu1 O2 2.361(5) 20_766 ? Eu1 O1 2.390(5) 16_546 ? Eu1 O1W 2.468(7) . ? Eu1 O2 2.801(5) 16_546 ? Eu1 C1 2.957(6) 16_546 ? Eu1 Eu1 4.0349(15) 29_757 ? O1 Eu1 2.390(5) 16_446 ? O2 Eu1 2.361(5) 24_755 ? O2 Eu1 2.801(5) 16_446 ? O4 Eu1 2.310(5) 11_656 ? O5 Eu1 2.328(5) 2_655 ? O6 Eu1 2.343(5) 18_567 ? O1W H1W 0.8200(11) . ? O1W H2W 0.8200(11) . ? 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 C1 O1 121.4(6) . . ? O2 C1 C2 120.1(6) . . ? O1 C1 C2 118.5(6) . . ? O2 C1 Eu1 70.6(4) . 16_446 ? O1 C1 Eu1 51.6(3) . 16_446 ? C2 C1 Eu1 165.4(5) . 16_446 ? C7 C2 C3 119.3(6) . . ? C7 C2 C1 119.5(6) . . ? C3 C2 C1 121.1(6) . . ? C4 C3 C2 120.3(6) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.9(6) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 118.1(6) . . ? C6 C5 C8 121.0(6) . . ? C4 C5 C8 120.9(6) . . ? C7 C6 C5 120.7(6) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 120.7(6) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? N1 C8 N3 124.6(6) . . ? N1 C8 C5 117.6(6) . . ? N3 C8 C5 117.7(6) . . ? O4 C9 O3 124.5(6) . . ? O4 C9 C10 117.9(6) . . ? O3 C9 C10 117.6(6) . . ? C15 C10 C11 119.7(6) . . ? C15 C10 C9 120.6(6) . . ? C11 C10 C9 119.7(6) . . ? C12 C11 C10 120.3(7) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.2(7) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 119.7(6) . . ? C12 C13 C16 120.5(6) . . ? C14 C13 C16 119.7(6) . . ? C15 C14 C13 119.2(7) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C10 C15 C14 120.6(6) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? N2 C16 N3 125.4(6) . . ? N2 C16 C13 118.8(6) . . ? N3 C16 C13 115.8(6) . . ? O5 C17 O6 124.9(7) . . ? O5 C17 C18 117.7(7) . . ? O6 C17 C18 117.4(7) . . ? C23 C18 C19 118.8(7) . . ? C23 C18 C17 119.9(6) . . ? C19 C18 C17 121.3(7) . . ? C20 C19 C18 120.7(7) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 120.5(7) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C20 118.4(7) . . ? C22 C21 C24 120.4(6) . . ? C20 C21 C24 121.2(6) . . ? C23 C22 C21 120.9(7) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C18 C23 C22 120.8(6) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? N1 C24 N2 124.4(7) . . ? N1 C24 C21 116.9(6) . . ? N2 C24 C21 118.7(6) . . ? O4 Eu1 O5 118.1(2) 11_656 2_655 ? O4 Eu1 O6 88.22(18) 11_656 30_657 ? O5 Eu1 O6 134.19(18) 2_655 30_657 ? O4 Eu1 O3 82.68(17) 11_656 . ? O5 Eu1 O3 75.76(19) 2_655 . ? O6 Eu1 O3 148.5(2) 30_657 . ? O4 Eu1 O2 79.70(18) 11_656 20_766 ? O5 Eu1 O2 72.64(19) 2_655 20_766 ? O6 Eu1 O2 76.7(2) 30_657 20_766 ? O3 Eu1 O2 130.4(2) . 20_766 ? O4 Eu1 O1 151.0(2) 11_656 16_546 ? O5 Eu1 O1 85.4(2) 2_655 16_546 ? O6 Eu1 O1 86.09(19) 30_657 16_546 ? O3 Eu1 O1 87.49(18) . 16_546 ? O2 Eu1 O1 126.15(18) 20_766 16_546 ? O4 Eu1 O1W 80.9(3) 11_656 . ? O5 Eu1 O1W 141.7(3) 2_655 . ? O6 Eu1 O1W 74.7(2) 30_657 . ? O3 Eu1 O1W 74.1(2) . . ? O2 Eu1 O1W 145.7(3) 20_766 . ? O1 Eu1 O1W 70.2(3) 16_546 . ? O4 Eu1 O2 149.74(16) 11_656 16_546 ? O5 Eu1 O2 73.32(17) 2_655 16_546 ? O6 Eu1 O2 67.35(17) 30_657 16_546 ? O3 Eu1 O2 127.44(16) . 16_546 ? O2 Eu1 O2 77.53(17) 20_766 16_546 ? O1 Eu1 O2 48.91(16) 16_546 16_546 ? O1W Eu1 O2 107.8(3) . 16_546 ? O4 Eu1 C1 160.43(19) 11_656 16_546 ? O5 Eu1 C1 80.7(2) 2_655 16_546 ? O6 Eu1 C1 73.56(19) 30_657 16_546 ? O3 Eu1 C1 109.13(19) . 16_546 ? O2 Eu1 C1 102.34(19) 20_766 16_546 ? O1 Eu1 C1 24.31(18) 16_546 16_546 ? O1W Eu1 C1 87.3(3) . 16_546 ? O2 Eu1 C1 24.81(17) 16_546 16_546 ? O4 Eu1 Eu1 119.68(13) 11_656 29_757 ? O5 Eu1 Eu1 68.04(13) 2_655 29_757 ? O6 Eu1 Eu1 66.31(13) 30_657 29_757 ? O3 Eu1 Eu1 143.25(13) . 29_757 ? O2 Eu1 Eu1 42.68(12) 20_766 29_757 ? O1 Eu1 Eu1 83.62(13) 16_546 29_757 ? O1W Eu1 Eu1 134.1(2) . 29_757 ? O2 Eu1 Eu1 34.85(10) 16_546 29_757 ? C1 Eu1 Eu1 59.65(14) 16_546 29_757 ? C8 N1 C24 115.4(6) . . ? C16 N2 C24 115.3(6) . . ? C16 N3 C8 114.8(6) . . ? C1 O1 Eu1 104.1(4) . 16_446 ? C1 O2 Eu1 172.9(5) . 24_755 ? C1 O2 Eu1 84.6(4) . 16_446 ? Eu1 O2 Eu1 102.47(17) 24_755 16_446 ? C9 O3 Eu1 143.9(5) . . ? C9 O4 Eu1 143.6(5) . 11_656 ? C17 O5 Eu1 135.8(5) . 2_655 ? C17 O6 Eu1 139.7(5) . 18_567 ? H1W O1W H2W 115(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.999 _refine_diff_density_min -1.100 _refine_diff_density_rms 0.200 data_z2 _database_code_depnum_ccdc_archive 'CCDC 915819' #TrackingRef 'CCDC-915819.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H30.67 Gd N2 Na0.33 O8, 2(H2 O)' _chemical_formula_sum 'C50 H34.67 Gd N2 Na0.33 O10' _chemical_formula_weight 988.38 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' Gd Gd -0.1653 3.9035 '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' 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 29.6966(13) _cell_length_b 29.6966(13) _cell_length_c 14.9618(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 11426.9(12) _cell_formula_units_Z 9 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 374 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 12.45 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4479 _exptl_absorpt_coefficient_mu 1.363 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6117 _exptl_absorpt_correction_T_max 0.8115 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 17266 _diffrn_reflns_av_R_equivalents 0.0762 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4951 _reflns_number_gt 3873 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction SAINT-Plus _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.4675P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4951 _refine_ls_number_parameters 303 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.1196 _refine_ls_R_factor_gt 0.0732 _refine_ls_wR_factor_ref 0.2671 _refine_ls_wR_factor_gt 0.2235 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5605(4) 0.2933(5) -0.0740(8) 0.028(3) Uani 1 1 d . . . C2 C 0.5113(4) 0.2778(5) -0.0283(9) 0.028(3) Uani 1 1 d . . . C3 C 0.4689(5) 0.2738(6) -0.0778(10) 0.044(4) Uani 1 1 d . . . H3 H 0.4721 0.2800 -0.1390 0.053 Uiso 1 1 calc R . . C4 C 0.4231(5) 0.2606(6) -0.0355(9) 0.041(3) Uani 1 1 d U . . H4 H 0.3951 0.2569 -0.0690 0.050 Uiso 1 1 calc R . . C5 C 0.4171(4) 0.2523(5) 0.0577(9) 0.030(3) Uani 1 1 d . . . C6 C 0.4591(4) 0.2576(5) 0.1068(7) 0.026(3) Uani 1 1 d . . . H6 H 0.4563 0.2531 0.1684 0.031 Uiso 1 1 calc R . . C7 C 0.5060(4) 0.2697(5) 0.0635(9) 0.033(3) Uani 1 1 d . . . H7 H 0.5336 0.2722 0.0967 0.039 Uiso 1 1 calc R . . C8 C 0.3658(4) 0.2362(5) 0.1006(8) 0.026(3) Uani 1 1 d . . . C9 C 0.3627(4) 0.2476(5) 0.1894(9) 0.035(3) Uani 1 1 d U . . H9 H 0.3926 0.2661 0.2238 0.042 Uiso 1 1 calc R . . C10 C 0.3138(5) 0.2305(6) 0.2257(10) 0.040(3) Uani 1 1 d . A . C11 C 0.2702(5) 0.2029(5) 0.1727(10) 0.035(3) Uani 1 1 d . . . H11 H 0.2370 0.1901 0.1965 0.042 Uiso 1 1 calc R . . C12 C 0.2767(4) 0.1944(5) 0.0817(8) 0.026(3) Uani 1 1 d . . . C13 C 0.3073(5) 0.2410(5) 0.3214(8) 0.049(4) Uani 1 1 d DU . . C14 C 0.2672(7) 0.2059(7) 0.3775(14) 0.066(6) Uani 0.56(3) 1 d PDU A 1 H14 H 0.2462 0.1714 0.3600 0.079 Uiso 0.56(3) 1 calc PR A 1 C15 C 0.2589(10) 0.2228(10) 0.4603(14) 0.080(8) Uani 0.56(3) 1 d PDU A 1 H15 H 0.2323 0.1995 0.4975 0.096 Uiso 0.56(3) 1 calc PR A 1 C16 C 0.2903(10) 0.2746(11) 0.4872(15) 0.068(8) Uani 0.56(3) 1 d PDU A 1 H16 H 0.2847 0.2856 0.5421 0.082 Uiso 0.56(3) 1 calc PR A 1 C17 C 0.3304(10) 0.3097(9) 0.4312(17) 0.088(10) Uani 0.56(3) 1 d PDU A 1 H17 H 0.3513 0.3441 0.4488 0.105 Uiso 0.56(3) 1 calc PR A 1 C18 C 0.3388(8) 0.2928(6) 0.3486(15) 0.063(7) Uani 0.56(3) 1 d PDU A 1 H18 H 0.3654 0.3162 0.3116 0.076 Uiso 0.56(3) 1 calc PR A 1 C14' C 0.2600(7) 0.2051(9) 0.3610(16) 0.066(6) Uani 0.44(3) 1 d PD A 2 H14' H 0.2340 0.1791 0.3263 0.079 Uiso 0.44(3) 1 calc PR A 2 C15' C 0.2516(11) 0.2081(13) 0.4526(17) 0.080(8) Uani 0.44(3) 1 d PD A 2 H15' H 0.2202 0.1842 0.4785 0.096 Uiso 0.44(3) 1 calc PR A 2 C16' C 0.2908(13) 0.2472(15) 0.5046(14) 0.068(8) Uani 0.44(3) 1 d PD A 2 H16' H 0.2855 0.2494 0.5654 0.082 Uiso 0.44(3) 1 calc PR A 2 C17' C 0.3381(12) 0.2831(14) 0.4650(16) 0.088(10) Uani 0.44(3) 1 d PD A 2 H17' H 0.3641 0.3091 0.4996 0.105 Uiso 0.44(3) 1 calc PR A 2 C18' C 0.3464(7) 0.2800(10) 0.3735(15) 0.063(7) Uani 0.44(3) 1 d PD A 2 H18' H 0.3779 0.3038 0.3476 0.076 Uiso 0.44(3) 1 calc PR A 2 C19 C 0.2312(4) 0.1650(4) 0.0214(8) 0.028(3) Uani 1 1 d . . . C20 C 0.1838(5) 0.1606(6) 0.0386(10) 0.040(3) Uani 1 1 d . . . H20 H 0.1805 0.1784 0.0870 0.048 Uiso 1 1 calc R . . C21 C 0.1412(5) 0.1306(6) -0.0140(9) 0.038(3) Uani 1 1 d . . . H21 H 0.1094 0.1279 -0.0003 0.046 Uiso 1 1 calc R . . C22 C 0.1453(4) 0.1038(4) -0.0889(8) 0.025(2) Uani 1 1 d . . . C23 C 0.1930(5) 0.1093(6) -0.1072(10) 0.038(3) Uani 1 1 d . . . H23 H 0.1969 0.0931 -0.1574 0.046 Uiso 1 1 calc R . . C24 C 0.2365(5) 0.1392(6) -0.0512(11) 0.047(4) Uani 1 1 d . . . H24 H 0.2683 0.1414 -0.0632 0.057 Uiso 1 1 calc R . . C25 C 0.0984(4) 0.0686(4) -0.1408(7) 0.022(2) Uani 1 1 d . . . Gd1 Gd 0.6667 0.3333 -0.1667 0.0177(6) Uani 1 6 d S . . Gd2 Gd 0.0000 0.0000 -0.23911(7) 0.0187(5) Uani 1 3 d S . . Na1 Na 0.0000 0.0000 0.0000 0.016(3) Uani 1 6 d S . . N1 N 0.3246(4) 0.2112(4) 0.0469(7) 0.034(2) Uani 1 1 d . . . H1 H 0.3284 0.2059 -0.0084 0.040 Uiso 1 1 calc R . . O1 O 0.6020(3) 0.3050(3) -0.0292(6) 0.0229(18) Uani 1 1 d . . . O2 O 0.5633(3) 0.2961(5) -0.1578(6) 0.042(3) Uani 1 1 d . . . O3 O 0.1000(3) 0.0455(4) -0.2090(6) 0.032(2) Uani 1 1 d . . . O4 O 0.0547(3) 0.0618(3) -0.1132(5) 0.0207(17) Uani 1 1 d . . . O1W O 0.1676(7) 0.0700(10) 0.6452(10) 0.157(11) 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 C1 0.021(5) 0.029(6) 0.027(7) -0.007(5) -0.007(5) 0.008(5) C2 0.018(5) 0.040(7) 0.026(6) 0.003(5) -0.004(5) 0.015(5) C3 0.022(6) 0.079(11) 0.027(7) 0.007(7) 0.001(6) 0.022(7) C4 0.018(5) 0.065(9) 0.033(7) 0.018(6) -0.005(5) 0.015(6) C5 0.020(6) 0.037(7) 0.031(7) -0.002(5) 0.001(5) 0.012(5) C6 0.020(5) 0.038(6) 0.013(6) 0.002(5) -0.007(4) 0.009(5) C7 0.009(5) 0.047(7) 0.032(7) 0.016(6) 0.004(5) 0.007(5) C8 0.019(5) 0.030(6) 0.029(7) -0.002(5) 0.004(5) 0.012(5) C9 0.007(5) 0.052(7) 0.032(7) -0.013(6) -0.007(4) 0.004(5) C10 0.015(5) 0.054(8) 0.041(8) -0.017(7) 0.006(5) 0.008(6) C11 0.020(6) 0.045(7) 0.035(7) -0.011(6) 0.004(5) 0.012(5) C12 0.023(6) 0.031(6) 0.022(6) 0.000(5) 0.004(5) 0.012(5) C13 0.043(7) 0.059(7) 0.031(6) -0.011(6) -0.002(5) 0.015(6) C14 0.051(9) 0.074(9) 0.058(10) -0.004(8) -0.003(7) 0.020(7) C15 0.078(11) 0.079(12) 0.068(10) -0.012(8) 0.011(8) 0.028(8) C16 0.072(10) 0.074(12) 0.053(10) -0.010(9) 0.008(8) 0.031(8) C17 0.090(12) 0.087(13) 0.077(12) -0.008(9) 0.001(9) 0.037(9) C18 0.061(10) 0.071(10) 0.044(10) -0.009(8) -0.005(8) 0.023(7) C14' 0.051(9) 0.074(9) 0.058(10) -0.004(8) -0.003(7) 0.020(7) C15' 0.078(11) 0.079(12) 0.068(10) -0.012(8) 0.011(8) 0.028(8) C16' 0.072(10) 0.074(12) 0.053(10) -0.010(9) 0.008(8) 0.031(8) C17' 0.090(12) 0.087(13) 0.077(12) -0.008(9) 0.001(9) 0.037(9) C18' 0.061(10) 0.071(10) 0.044(10) -0.009(8) -0.005(8) 0.023(7) C19 0.017(5) 0.026(6) 0.028(6) -0.007(5) 0.000(5) 0.000(5) C20 0.028(6) 0.050(8) 0.041(8) -0.030(7) -0.008(6) 0.019(6) C21 0.023(6) 0.055(8) 0.034(7) -0.018(6) -0.008(5) 0.018(6) C22 0.021(5) 0.023(5) 0.029(6) -0.004(5) -0.006(5) 0.009(5) C23 0.032(7) 0.051(8) 0.030(7) -0.013(6) -0.005(6) 0.019(6) C24 0.018(6) 0.051(9) 0.061(10) -0.013(8) 0.010(6) 0.009(6) C25 0.020(5) 0.020(5) 0.015(5) 0.005(4) 0.000(4) 0.002(4) Gd1 0.0207(6) 0.0207(6) 0.0117(9) 0.000 0.000 0.0103(3) Gd2 0.0211(6) 0.0211(6) 0.0138(8) 0.000 0.000 0.0106(3) Na1 0.016(3) 0.016(3) 0.015(6) 0.000 0.000 0.0081(17) N1 0.022(5) 0.040(6) 0.028(6) -0.004(5) -0.001(4) 0.007(5) O1 0.015(4) 0.029(4) 0.024(4) -0.004(4) -0.001(3) 0.010(3) O2 0.021(4) 0.084(8) 0.018(5) 0.008(5) 0.007(3) 0.025(5) O3 0.019(4) 0.051(6) 0.021(5) -0.003(4) 0.001(3) 0.013(4) O4 0.014(4) 0.023(4) 0.020(4) -0.007(3) 0.002(3) 0.005(3) O1W 0.060(10) 0.32(3) 0.041(9) -0.039(14) 0.001(8) 0.054(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 O2 1.256(16) . ? C1 O1 1.289(14) . ? C1 C2 1.463(17) . ? C2 C3 1.413(17) . ? C2 C7 1.390(18) . ? C3 C4 1.369(18) . ? C3 H3 0.9300 . ? C4 C5 1.410(18) . ? C4 H4 0.9300 . ? C5 C6 1.385(16) . ? C5 C8 1.494(15) . ? C6 C7 1.410(16) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N1 1.337(15) . ? C8 C9 1.386(17) . ? C9 C10 1.388(16) . ? C9 H9 0.9300 . ? C10 C11 1.386(18) . ? C10 C13 1.497(17) . ? C11 C12 1.415(18) . ? C11 H11 0.9300 . ? C12 N1 1.355(15) . ? C12 C19 1.490(16) . ? C13 C18' 1.397(9) . ? C13 C14' 1.401(9) . ? C13 C14 1.403(9) . ? C13 C18 1.405(9) . ? C14 C15 1.405(9) . ? C14 H14 0.9300 . ? C15 C16 1.401(9) . ? C15 H15 0.9300 . ? C16 C17 1.401(9) . ? C16 H16 0.9300 . ? C17 C18 1.402(9) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C14' C15' 1.403(9) . ? C14' H14' 0.9300 . ? C15' C16' 1.400(10) . ? C15' H15' 0.9300 . ? C16' C17' 1.400(10) . ? C16' H16' 0.9300 . ? C17' C18' 1.402(9) . ? C17' H17' 0.9300 . ? C18' H18' 0.9300 . ? C19 C20 1.372(17) . ? C19 C24 1.382(19) . ? C20 C21 1.374(17) . ? C20 H20 0.9300 . ? C21 C22 1.414(17) . ? C21 H21 0.9300 . ? C22 C23 1.370(18) . ? C22 C25 1.477(15) . ? C23 C24 1.42(2) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 O3 1.244(14) . ? C25 O4 1.278(13) . ? Gd1 O1 2.648(8) 17_554 ? Gd1 O1 2.648(8) 2_655 ? Gd1 O1 2.648(8) 3_665 ? Gd1 O1 2.648(8) . ? Gd1 O1 2.648(8) 18_544 ? Gd1 O1 2.648(8) 16_654 ? Gd1 O2 2.696(8) 17_554 ? Gd1 O2 2.696(8) 2_655 ? Gd1 O2 2.696(8) 3_665 ? Gd1 O2 2.696(8) . ? Gd1 O2 2.696(8) 18_544 ? Gd1 O2 2.696(8) 16_654 ? Gd2 O1 2.488(8) 7_444 ? Gd2 O1 2.488(8) 9_554 ? Gd2 O1 2.488(8) 8_544 ? Gd2 O4 2.563(8) . ? Gd2 O4 2.563(8) 3 ? Gd2 O4 2.563(8) 2 ? Gd2 O3 2.615(8) . ? Gd2 O3 2.615(8) 3 ? Gd2 O3 2.615(8) 2 ? Na1 O4 2.427(8) 2 ? Na1 O4 2.427(8) 3 ? Na1 O4 2.427(8) 11 ? Na1 O4 2.427(8) 12 ? Na1 O4 2.427(8) . ? Na1 O4 2.427(8) 10 ? Na1 Gd2 3.5775(11) 10 ? N1 H1 0.8600 . ? O1 Gd2 2.488(8) 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 C1 O1 118.6(11) . . ? O2 C1 C2 120.7(11) . . ? O1 C1 C2 120.7(11) . . ? C3 C2 C7 118.9(11) . . ? C3 C2 C1 119.3(12) . . ? C7 C2 C1 121.7(11) . . ? C4 C3 C2 119.8(13) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 121.8(12) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C6 C5 C4 118.5(11) . . ? C6 C5 C8 121.5(11) . . ? C4 C5 C8 120.0(11) . . ? C5 C6 C7 120.2(11) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 120.7(11) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? N1 C8 C9 123.9(10) . . ? N1 C8 C5 115.1(11) . . ? C9 C8 C5 121.0(11) . . ? C10 C9 C8 118.1(11) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? C9 C10 C11 119.4(12) . . ? C9 C10 C13 121.2(11) . . ? C11 C10 C13 119.4(10) . . ? C10 C11 C12 119.1(11) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? N1 C12 C11 121.1(11) . . ? N1 C12 C19 117.4(10) . . ? C11 C12 C19 121.5(10) . . ? C18' C13 C14' 119.7(11) . . ? C18' C13 C14 109.0(13) . . ? C14' C13 C14 13.1(17) . . ? C18' C13 C18 26.8(15) . . ? C14' C13 C18 125.1(14) . . ? C14 C13 C18 119.6(11) . . ? C18' C13 C10 124.4(13) . . ? C14' C13 C10 115.5(13) . . ? C14 C13 C10 124.6(13) . . ? C18 C13 C10 114.8(12) . . ? C13 C14 C15 119.9(12) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 120.4(12) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.8(12) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 119.9(12) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 120.5(12) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? C13 C14' C15' 120.4(12) . . ? C13 C14' H14' 119.8 . . ? C15' C14' H14' 119.8 . . ? C16' C15' C14' 119.7(12) . . ? C16' C15' H15' 120.1 . . ? C14' C15' H15' 120.1 . . ? C15' C16' C17' 119.8(12) . . ? C15' C16' H16' 120.1 . . ? C17' C16' H16' 120.1 . . ? C16' C17' C18' 120.4(12) . . ? C16' C17' H17' 119.8 . . ? C18' C17' H17' 119.8 . . ? C13 C18' C17' 119.9(12) . . ? C13 C18' H18' 120.0 . . ? C17' C18' H18' 120.0 . . ? C20 C19 C24 119.4(12) . . ? C20 C19 C12 121.8(11) . . ? C24 C19 C12 118.7(11) . . ? C19 C20 C21 121.5(12) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C20 C21 C22 120.6(11) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C23 C22 C21 117.8(11) . . ? C23 C22 C25 122.2(11) . . ? C21 C22 C25 119.9(10) . . ? C22 C23 C24 121.4(13) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C19 C24 C23 119.3(12) . . ? C19 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? O3 C25 O4 119.6(10) . . ? O3 C25 C22 122.6(11) . . ? O4 C25 C22 117.8(10) . . ? C22 C25 Gd2 176.4(8) . . ? O1 Gd1 O1 179.997(1) 17_554 2_655 ? O1 Gd1 O1 113.9(3) 17_554 3_665 ? O1 Gd1 O1 66.1(3) 2_655 3_665 ? O1 Gd1 O1 113.9(3) 17_554 . ? O1 Gd1 O1 66.1(3) 2_655 . ? O1 Gd1 O1 66.1(3) 3_665 . ? O1 Gd1 O1 66.1(3) 17_554 18_544 ? O1 Gd1 O1 113.9(3) 2_655 18_544 ? O1 Gd1 O1 179.997(1) 3_665 18_544 ? O1 Gd1 O1 113.9(3) . 18_544 ? O1 Gd1 O1 66.1(3) 17_554 16_654 ? O1 Gd1 O1 113.9(3) 2_655 16_654 ? O1 Gd1 O1 113.9(3) 3_665 16_654 ? O1 Gd1 O1 179.998(1) . 16_654 ? O1 Gd1 O1 66.1(3) 18_544 16_654 ? O1 Gd1 O2 48.3(3) 17_554 17_554 ? O1 Gd1 O2 131.7(3) 2_655 17_554 ? O1 Gd1 O2 71.1(3) 3_665 17_554 ? O1 Gd1 O2 76.9(3) . 17_554 ? O1 Gd1 O2 108.9(3) 18_544 17_554 ? O1 Gd1 O2 103.1(3) 16_654 17_554 ? O1 Gd1 O2 131.7(3) 17_554 2_655 ? O1 Gd1 O2 48.3(3) 2_655 2_655 ? O1 Gd1 O2 108.9(3) 3_665 2_655 ? O1 Gd1 O2 103.1(3) . 2_655 ? O1 Gd1 O2 71.1(3) 18_544 2_655 ? O1 Gd1 O2 76.9(3) 16_654 2_655 ? O2 Gd1 O2 179.999(1) 17_554 2_655 ? O1 Gd1 O2 76.9(3) 17_554 3_665 ? O1 Gd1 O2 103.1(3) 2_655 3_665 ? O1 Gd1 O2 48.3(3) 3_665 3_665 ? O1 Gd1 O2 108.9(3) . 3_665 ? O1 Gd1 O2 131.7(3) 18_544 3_665 ? O1 Gd1 O2 71.1(3) 16_654 3_665 ? O2 Gd1 O2 60.24(3) 17_554 3_665 ? O2 Gd1 O2 119.76(3) 2_655 3_665 ? O1 Gd1 O2 71.1(3) 17_554 . ? O1 Gd1 O2 108.9(3) 2_655 . ? O1 Gd1 O2 103.1(3) 3_665 . ? O1 Gd1 O2 48.3(3) . . ? O1 Gd1 O2 76.9(3) 18_544 . ? O1 Gd1 O2 131.7(3) 16_654 . ? O2 Gd1 O2 60.24(3) 17_554 . ? O2 Gd1 O2 119.76(3) 2_655 . ? O2 Gd1 O2 119.76(3) 3_665 . ? O1 Gd1 O2 103.1(3) 17_554 18_544 ? O1 Gd1 O2 76.9(3) 2_655 18_544 ? O1 Gd1 O2 131.7(3) 3_665 18_544 ? O1 Gd1 O2 71.1(3) . 18_544 ? O1 Gd1 O2 48.3(3) 18_544 18_544 ? O1 Gd1 O2 108.8(3) 16_654 18_544 ? O2 Gd1 O2 119.76(3) 17_554 18_544 ? O2 Gd1 O2 60.24(3) 2_655 18_544 ? O2 Gd1 O2 179.997(1) 3_665 18_544 ? O2 Gd1 O2 60.24(3) . 18_544 ? O1 Gd1 O2 108.9(3) 17_554 16_654 ? O1 Gd1 O2 71.1(3) 2_655 16_654 ? O1 Gd1 O2 76.9(3) 3_665 16_654 ? O1 Gd1 O2 131.7(3) . 16_654 ? O1 Gd1 O2 103.1(3) 18_544 16_654 ? O1 Gd1 O2 48.3(3) 16_654 16_654 ? O2 Gd1 O2 119.76(3) 17_554 16_654 ? O2 Gd1 O2 60.24(3) 2_655 16_654 ? O2 Gd1 O2 60.24(3) 3_665 16_654 ? O2 Gd1 O2 180.0 . 16_654 ? O2 Gd1 O2 119.75(3) 18_544 16_654 ? O1 Gd2 O1 71.0(3) 7_444 9_554 ? O1 Gd2 O1 71.0(3) 7_444 8_544 ? O1 Gd2 O1 71.0(3) 9_554 8_544 ? O1 Gd2 O4 153.3(3) 7_444 . ? O1 Gd2 O4 96.8(2) 9_554 . ? O1 Gd2 O4 128.7(3) 8_544 . ? O1 Gd2 O4 128.7(3) 7_444 3 ? O1 Gd2 O4 153.3(3) 9_554 3 ? O1 Gd2 O4 96.8(2) 8_544 3 ? O4 Gd2 O4 71.9(3) . 3 ? O1 Gd2 O4 96.8(2) 7_444 2 ? O1 Gd2 O4 128.7(3) 9_554 2 ? O1 Gd2 O4 153.3(3) 8_544 2 ? O4 Gd2 O4 71.9(3) . 2 ? O4 Gd2 O4 71.9(3) 3 2 ? O1 Gd2 O3 142.0(3) 7_444 . ? O1 Gd2 O3 77.7(3) 9_554 . ? O1 Gd2 O3 79.0(3) 8_544 . ? O4 Gd2 O3 49.8(2) . . ? O4 Gd2 O3 76.6(3) 3 . ? O4 Gd2 O3 119.8(3) 2 . ? O1 Gd2 O3 79.0(3) 7_444 3 ? O1 Gd2 O3 142.0(3) 9_554 3 ? O1 Gd2 O3 77.7(3) 8_544 3 ? O4 Gd2 O3 119.8(3) . 3 ? O4 Gd2 O3 49.8(2) 3 3 ? O4 Gd2 O3 76.6(3) 2 3 ? O3 Gd2 O3 117.09(11) . 3 ? O1 Gd2 O3 77.7(3) 7_444 2 ? O1 Gd2 O3 79.0(3) 9_554 2 ? O1 Gd2 O3 142.0(3) 8_544 2 ? O4 Gd2 O3 76.6(3) . 2 ? O4 Gd2 O3 119.8(3) 3 2 ? O4 Gd2 O3 49.8(2) 2 2 ? O3 Gd2 O3 117.09(11) . 2 ? O3 Gd2 O3 117.09(11) 3 2 ? O4 Na1 O4 76.7(3) 2 3 ? O4 Na1 O4 180.0(4) 2 11 ? O4 Na1 O4 103.3(3) 3 11 ? O4 Na1 O4 103.3(3) 2 12 ? O4 Na1 O4 180.0(5) 3 12 ? O4 Na1 O4 76.7(3) 11 12 ? O4 Na1 O4 76.7(3) 2 . ? O4 Na1 O4 76.7(3) 3 . ? O4 Na1 O4 103.3(3) 11 . ? O4 Na1 O4 103.3(3) 12 . ? O4 Na1 O4 103.3(3) 2 10 ? O4 Na1 O4 103.3(3) 3 10 ? O4 Na1 O4 76.7(3) 11 10 ? O4 Na1 O4 76.7(3) 12 10 ? O4 Na1 O4 180.0(7) . 10 ? C8 N1 C12 118.4(11) . . ? C8 N1 H1 120.8 . . ? C12 N1 H1 120.8 . . ? C1 O1 Gd2 161.7(8) . 4 ? C1 O1 Gd1 97.2(7) . . ? Gd2 O1 Gd1 98.9(2) 4 . ? C1 O2 Gd1 95.8(7) . . ? C25 O3 Gd2 94.5(7) . . ? C25 O4 Na1 126.0(7) . . ? C25 O4 Gd2 96.1(6) . . ? Na1 O4 Gd2 91.5(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.816 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.168 data_z3 _database_code_depnum_ccdc_archive 'CCDC 915820' #TrackingRef 'CCDC-915820.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H30.67 N2 Na0.33 O8 Pr, 2(H2 O)' _chemical_formula_sum 'C50 H34.67 N2 Na0.33 O10 Pr' _chemical_formula_weight 972.03 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 29.5657(12) _cell_length_b 29.5657(12) _cell_length_c 14.8222(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 11220.7(11) _cell_formula_units_Z 9 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1738 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 19.03 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4422 _exptl_absorpt_coefficient_mu 1.035 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6823 _exptl_absorpt_correction_T_max 0.8519 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 19312 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4858 _reflns_number_gt 4250 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction SAINT-Plus _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+44.0916P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4858 _refine_ls_number_parameters 303 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.56215(13) 0.29357(14) -0.0760(2) 0.0310(8) Uani 1 1 d . . . C2 C 0.51199(13) 0.27843(15) -0.0289(2) 0.0328(8) Uani 1 1 d . . . C3 C 0.46983(16) 0.2737(2) -0.0788(3) 0.0513(12) Uani 1 1 d . . . H3 H 0.4730 0.2795 -0.1407 0.062 Uiso 1 1 calc R . . C4 C 0.42364(16) 0.2606(2) -0.0359(3) 0.0534(12) Uani 1 1 d . . . H4 H 0.3958 0.2575 -0.0697 0.064 Uiso 1 1 calc R . . C5 C 0.41739(14) 0.25174(16) 0.0554(3) 0.0369(9) Uani 1 1 d . . . C6 C 0.45983(14) 0.25722(16) 0.1053(3) 0.0376(9) Uani 1 1 d . . . H6 H 0.4569 0.2526 0.1675 0.045 Uiso 1 1 calc R . . C7 C 0.50626(13) 0.26953(15) 0.0630(2) 0.0324(8) Uani 1 1 d . . . H7 H 0.5339 0.2718 0.0967 0.039 Uiso 1 1 calc R . . C8 C 0.36619(14) 0.23541(16) 0.0989(3) 0.0366(9) Uani 1 1 d . . . C9 C 0.36206(14) 0.24650(17) 0.1880(3) 0.0427(10) Uani 1 1 d . . . H9 H 0.3919 0.2650 0.2230 0.051 Uiso 1 1 calc R . . C10 C 0.31325(15) 0.23003(17) 0.2250(3) 0.0426(10) Uani 1 1 d . A . C11 C 0.27024(14) 0.20336(16) 0.1691(3) 0.0387(9) Uani 1 1 d . . . H11 H 0.2368 0.1917 0.1915 0.046 Uiso 1 1 calc R . . C12 C 0.27688(13) 0.19414(15) 0.0807(3) 0.0345(8) Uani 1 1 d . . . C13 C 0.30664(15) 0.24061(19) 0.3205(3) 0.0634(15) Uani 1 1 d D . . C14 C 0.2669(3) 0.2037(4) 0.3756(7) 0.072(2) Uani 0.584(10) 1 d PDU A 1 H14 H 0.2459 0.1694 0.3561 0.086 Uiso 0.584(10) 1 calc PR A 1 C15 C 0.2594(5) 0.2196(5) 0.4612(8) 0.113(3) Uani 0.584(10) 1 d PDU A 1 H15 H 0.2332 0.1955 0.4988 0.136 Uiso 0.584(10) 1 calc PR A 1 C16 C 0.2909(4) 0.2711(5) 0.4904(7) 0.097(4) Uani 0.584(10) 1 d PDU A 1 H16 H 0.2852 0.2811 0.5469 0.117 Uiso 0.584(10) 1 calc PR A 1 C17 C 0.3304(4) 0.3074(4) 0.4363(7) 0.094(3) Uani 0.584(10) 1 d PDU A 1 H17 H 0.3517 0.3413 0.4567 0.112 Uiso 0.584(10) 1 calc PR A 1 C18 C 0.3383(3) 0.2928(3) 0.3502(6) 0.075(3) Uani 0.584(10) 1 d PDU A 1 H18 H 0.3643 0.3173 0.3127 0.090 Uiso 0.584(10) 1 calc PR A 1 C14' C 0.2591(4) 0.2062(5) 0.3629(10) 0.072(2) Uani 0.416(10) 1 d PD A 2 H14' H 0.2316 0.1813 0.3283 0.086 Uiso 0.416(10) 1 calc PR A 2 C15' C 0.2520(6) 0.2083(6) 0.4560(10) 0.113(3) Uani 0.416(10) 1 d PD A 2 H15' H 0.2201 0.1851 0.4825 0.136 Uiso 0.416(10) 1 calc PR A 2 C16' C 0.2929(6) 0.2455(6) 0.5092(10) 0.097(4) Uani 0.416(10) 1 d PD A 2 H16' H 0.2888 0.2473 0.5711 0.117 Uiso 0.416(10) 1 calc PR A 2 C17' C 0.3399(5) 0.2797(6) 0.4673(8) 0.094(3) Uani 0.416(10) 1 d PD A 2 H17' H 0.3674 0.3050 0.5014 0.112 Uiso 0.416(10) 1 calc PR A 2 C18' C 0.3464(4) 0.2766(5) 0.3747(8) 0.075(3) Uani 0.416(10) 1 d PD A 2 H18' H 0.3785 0.2995 0.3486 0.090 Uiso 0.416(10) 1 calc PR A 2 C19 C 0.23129(13) 0.16407(15) 0.0188(2) 0.0325(8) Uani 1 1 d . . . C20 C 0.18337(15) 0.15977(19) 0.0367(3) 0.0505(12) Uani 1 1 d . . . H20 H 0.1799 0.1774 0.0858 0.061 Uiso 1 1 calc R . . C21 C 0.14093(14) 0.12995(17) -0.0170(3) 0.0427(10) Uani 1 1 d . . . H21 H 0.1091 0.1277 -0.0037 0.051 Uiso 1 1 calc R . . C22 C 0.14453(13) 0.10331(13) -0.0901(2) 0.0281(7) Uani 1 1 d . . . C23 C 0.19242(14) 0.10788(17) -0.1099(3) 0.0422(10) Uani 1 1 d . . . H23 H 0.1958 0.0908 -0.1600 0.051 Uiso 1 1 calc R . . C24 C 0.23554(14) 0.13800(17) -0.0551(3) 0.0450(10) Uani 1 1 d . . . H24 H 0.2675 0.1406 -0.0684 0.054 Uiso 1 1 calc R . . C25 C 0.09630(13) 0.06743(13) -0.1426(2) 0.0249(7) Uani 1 1 d . . . N1 N 0.32431(11) 0.21025(13) 0.0446(2) 0.0387(8) Uani 1 1 d . . . H1 H 0.3278 0.2047 -0.0112 0.046 Uiso 0.33 1 calc PR . . Na1 Na 0.0000 0.0000 0.0000 0.0297(7) Uani 1 6 d S . . O1 O 0.60266(9) 0.30518(9) -0.02902(15) 0.0278(5) Uani 1 1 d . . . O2 O 0.56396(11) 0.29460(14) -0.15927(18) 0.0524(8) Uani 1 1 d . . . O3 O 0.09886(9) 0.04445(10) -0.21145(16) 0.0355(6) Uani 1 1 d . . . O4 O 0.05287(8) 0.06095(9) -0.11472(16) 0.0268(5) Uani 1 1 d . . . O1W O 0.16715(19) 0.0665(3) 0.6441(3) 0.171(3) Uani 1 1 d . . . Pr1 Pr 0.6667 0.3333 -0.1667 0.01777(12) Uani 1 6 d S . . Pr2 Pr 0.0000 0.0000 -0.240367(19) 0.01814(11) Uani 1 3 d S . . 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 C1 0.0231(17) 0.039(2) 0.0274(18) 0.0034(15) 0.0016(14) 0.0133(15) C2 0.0196(16) 0.046(2) 0.0292(19) 0.0039(16) -0.0013(14) 0.0139(16) C3 0.030(2) 0.090(4) 0.031(2) 0.010(2) -0.0001(17) 0.028(2) C4 0.027(2) 0.099(4) 0.035(2) 0.004(2) -0.0061(17) 0.032(2) C5 0.0213(17) 0.050(2) 0.033(2) -0.0030(17) -0.0001(15) 0.0135(17) C6 0.0237(18) 0.053(2) 0.0259(18) 0.0008(17) 0.0002(14) 0.0112(17) C7 0.0194(16) 0.044(2) 0.0273(18) -0.0009(16) -0.0051(14) 0.0110(15) C8 0.0200(17) 0.044(2) 0.039(2) -0.0018(17) -0.0001(15) 0.0117(16) C9 0.0201(18) 0.056(3) 0.041(2) -0.0111(19) -0.0044(16) 0.0105(17) C10 0.0284(19) 0.052(2) 0.041(2) -0.0094(19) 0.0009(17) 0.0152(18) C11 0.0174(17) 0.047(2) 0.042(2) -0.0083(18) 0.0004(15) 0.0089(16) C12 0.0189(16) 0.036(2) 0.041(2) -0.0049(17) -0.0014(15) 0.0082(15) C13 0.034(2) 0.092(4) 0.047(3) -0.025(3) -0.001(2) 0.019(2) C14 0.060(4) 0.094(4) 0.052(4) -0.008(3) 0.005(3) 0.030(3) C15 0.097(5) 0.130(6) 0.080(4) -0.028(4) 0.022(4) 0.032(4) C16 0.100(5) 0.106(7) 0.072(5) -0.027(5) 0.014(4) 0.042(4) C17 0.082(5) 0.096(6) 0.079(5) -0.039(4) -0.006(4) 0.027(4) C18 0.049(4) 0.092(5) 0.059(5) -0.026(4) -0.006(3) 0.017(3) C14' 0.060(4) 0.094(4) 0.052(4) -0.008(3) 0.005(3) 0.030(3) C15' 0.097(5) 0.130(6) 0.080(4) -0.028(4) 0.022(4) 0.032(4) C16' 0.100(5) 0.106(7) 0.072(5) -0.027(5) 0.014(4) 0.042(4) C17' 0.082(5) 0.096(6) 0.079(5) -0.039(4) -0.006(4) 0.027(4) C18' 0.049(4) 0.092(5) 0.059(5) -0.026(4) -0.006(3) 0.017(3) C19 0.0199(17) 0.039(2) 0.0325(19) -0.0030(16) -0.0025(14) 0.0101(15) C20 0.028(2) 0.069(3) 0.055(3) -0.033(2) -0.0112(18) 0.025(2) C21 0.0220(18) 0.053(2) 0.053(2) -0.023(2) -0.0081(17) 0.0186(18) C22 0.0230(17) 0.0301(18) 0.0262(17) 0.0025(14) -0.0014(14) 0.0096(14) C23 0.0273(19) 0.058(3) 0.035(2) -0.0102(19) 0.0030(16) 0.0172(19) C24 0.0209(18) 0.062(3) 0.044(2) -0.010(2) 0.0025(16) 0.0150(18) C25 0.0246(16) 0.0254(16) 0.0220(16) 0.0026(13) -0.0006(13) 0.0105(14) N1 0.0210(15) 0.052(2) 0.0382(18) -0.0036(15) -0.0017(13) 0.0142(14) Na1 0.0366(11) 0.0366(11) 0.0158(15) 0.000 0.000 0.0183(6) O1 0.0189(11) 0.0374(14) 0.0242(12) 0.0015(10) -0.0013(9) 0.0120(10) O2 0.0326(15) 0.093(2) 0.0272(15) 0.0057(15) 0.0016(12) 0.0280(16) O3 0.0271(13) 0.0486(16) 0.0278(13) -0.0100(12) -0.0011(10) 0.0165(12) O4 0.0210(11) 0.0259(12) 0.0279(12) -0.0021(10) 0.0004(9) 0.0077(10) O1W 0.069(3) 0.366(10) 0.060(3) -0.035(4) -0.003(2) 0.095(5) Pr1 0.01928(15) 0.01928(15) 0.0147(2) 0.000 0.000 0.00964(8) Pr2 0.01975(13) 0.01975(13) 0.01492(16) 0.000 0.000 0.00987(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 O2 1.235(4) . ? C1 O1 1.275(4) . ? C1 C2 1.491(5) . ? C1 Pr1 3.017(3) . ? C2 C7 1.383(5) . ? C2 C3 1.394(5) . ? C3 C4 1.374(6) . ? C3 H3 0.9300 . ? C4 C5 1.373(5) . ? C4 H4 0.9300 . ? C5 C6 1.394(5) . ? C5 C8 1.487(5) . ? C6 C7 1.382(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N1 1.346(5) . ? C8 C9 1.381(5) . ? C9 C10 1.385(5) . ? C9 H9 0.9300 . ? C10 C11 1.387(5) . ? C10 C13 1.483(6) . ? C11 C12 1.373(5) . ? C11 H11 0.9300 . ? C12 N1 1.345(5) . ? C12 C19 1.500(5) . ? C13 C18' 1.382(8) . ? C13 C14 1.400(8) . ? C13 C14' 1.406(9) . ? C13 C18 1.416(8) . ? C14 C15 1.409(8) . ? C14 H14 0.9300 . ? C15 C16 1.400(9) . ? C15 H15 0.9300 . ? C16 C17 1.380(8) . ? C16 H16 0.9300 . ? C17 C18 1.404(8) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C14' C15' 1.402(9) . ? C14' H14' 0.9300 . ? C15' C16' 1.402(9) . ? C15' H15' 0.9300 . ? C16' C17' 1.391(9) . ? C16' H16' 0.9300 . ? C17' C18' 1.395(9) . ? C17' H17' 0.9300 . ? C18' H18' 0.9300 . ? C19 C24 1.381(5) . ? C19 C20 1.383(5) . ? C20 C21 1.371(5) . ? C20 H20 0.9300 . ? C21 C22 1.375(5) . ? C21 H21 0.9300 . ? C22 C23 1.385(5) . ? C22 C25 1.500(4) . ? C23 C24 1.394(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 O3 1.249(4) . ? C25 O4 1.269(4) . ? C25 Pr2 2.916(3) . ? N1 H1 0.8600 . ? Na1 O4 2.401(2) 12 ? Na1 O4 2.401(2) 11 ? Na1 O4 2.401(2) 3 ? Na1 O4 2.401(2) 10 ? Na1 O4 2.401(2) 2 ? Na1 O4 2.401(2) . ? O1 Pr2 2.443(2) 4 ? O1 Pr1 2.619(2) . ? O2 Pr1 2.658(3) . ? O3 Pr2 2.571(2) . ? O4 Pr2 2.518(2) . ? Pr1 O1 2.619(2) 17_554 ? Pr1 O1 2.619(2) 2_655 ? Pr1 O1 2.619(2) 3_665 ? Pr1 O1 2.619(2) 18_544 ? Pr1 O1 2.619(2) 16_654 ? Pr1 O2 2.658(3) 17_554 ? Pr1 O2 2.658(3) 2_655 ? Pr1 O2 2.658(3) 3_665 ? Pr1 O2 2.658(3) 18_544 ? Pr1 O2 2.658(3) 16_654 ? Pr2 O1 2.443(2) 7_444 ? Pr2 O1 2.443(2) 9_554 ? Pr2 O1 2.443(2) 8_544 ? Pr2 O4 2.518(2) 3 ? Pr2 O4 2.518(2) 2 ? Pr2 O3 2.571(2) 2 ? Pr2 O3 2.571(2) 3 ? 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 C1 O1 121.1(3) . . ? O2 C1 C2 120.0(3) . . ? O1 C1 C2 119.0(3) . . ? O2 C1 Pr1 61.45(19) . . ? O1 C1 Pr1 59.82(17) . . ? C2 C1 Pr1 175.3(3) . . ? C7 C2 C3 119.0(3) . . ? C7 C2 C1 121.8(3) . . ? C3 C2 C1 119.2(3) . . ? C4 C3 C2 119.7(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 122.0(4) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 118.2(3) . . ? C4 C5 C8 120.5(3) . . ? C6 C5 C8 121.3(3) . . ? C7 C6 C5 120.5(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 120.5(3) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? N1 C8 C9 122.5(3) . . ? N1 C8 C5 115.2(3) . . ? C9 C8 C5 122.3(3) . . ? C8 C9 C10 119.7(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C9 C10 C11 117.5(4) . . ? C9 C10 C13 121.9(4) . . ? C11 C10 C13 120.7(3) . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? N1 C12 C11 122.4(3) . . ? N1 C12 C19 115.9(3) . . ? C11 C12 C19 121.7(3) . . ? C18' C13 C14 108.7(7) . . ? C18' C13 C14' 117.0(8) . . ? C14 C13 C14' 13.6(9) . . ? C18' C13 C18 30.2(6) . . ? C14 C13 C18 120.6(7) . . ? C14' C13 C18 121.8(8) . . ? C18' C13 C10 124.5(6) . . ? C14 C13 C10 122.7(6) . . ? C14' C13 C10 117.6(7) . . ? C18 C13 C10 116.2(5) . . ? C13 C14 C15 118.5(9) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C16 C15 C14 120.7(9) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.7(8) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.8(8) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 119.7(7) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? C15' C14' C13 121.7(11) . . ? C15' C14' H14' 119.1 . . ? C13 C14' H14' 119.1 . . ? C16' C15' C14' 119.9(11) . . ? C16' C15' H15' 120.0 . . ? C14' C15' H15' 120.0 . . ? C17' C16' C15' 118.5(10) . . ? C17' C16' H16' 120.8 . . ? C15' C16' H16' 120.8 . . ? C16' C17' C18' 120.7(10) . . ? C16' C17' H17' 119.6 . . ? C18' C17' H17' 119.6 . . ? C13 C18' C17' 122.1(9) . . ? C13 C18' H18' 118.9 . . ? C17' C18' H18' 118.9 . . ? C24 C19 C20 118.4(3) . . ? C24 C19 C12 120.7(3) . . ? C20 C19 C12 120.9(3) . . ? C21 C20 C19 121.0(4) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 121.2(3) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C21 C22 C23 118.7(3) . . ? C21 C22 C25 119.7(3) . . ? C23 C22 C25 121.5(3) . . ? C22 C23 C24 120.2(4) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C19 C24 C23 120.6(3) . . ? C19 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? O3 C25 O4 121.1(3) . . ? O3 C25 C22 120.9(3) . . ? O4 C25 C22 118.1(3) . . ? C12 N1 C8 117.8(3) . . ? C12 N1 H1 121.1 . . ? C8 N1 H1 121.1 . . ? O4 Na1 O4 75.39(8) 12 11 ? O4 Na1 O4 180.00(13) 12 3 ? O4 Na1 O4 104.61(8) 11 3 ? O4 Na1 O4 75.39(8) 12 10 ? O4 Na1 O4 75.39(8) 11 10 ? O4 Na1 O4 104.61(8) 3 10 ? O4 Na1 O4 104.61(8) 12 2 ? O4 Na1 O4 180.00(13) 11 2 ? O4 Na1 O4 75.39(8) 3 2 ? O4 Na1 O4 104.61(8) 10 2 ? O4 Na1 O4 104.61(8) 12 . ? O4 Na1 O4 104.61(8) 11 . ? O4 Na1 O4 75.39(8) 3 . ? O4 Na1 O4 180.0(2) 10 . ? O4 Na1 O4 75.39(8) 2 . ? C1 O1 Pr2 163.6(2) . 4 ? C1 O1 Pr1 95.3(2) . . ? Pr2 O1 Pr1 98.90(8) 4 . ? C1 O2 Pr1 94.5(2) . . ? C25 O3 Pr2 93.0(2) . . ? C25 O4 Na1 125.0(2) . . ? C25 O4 Pr2 94.96(19) . . ? Na1 O4 Pr2 92.78(7) . . ? O1 Pr1 O1 180.0 17_554 2_655 ? O1 Pr1 O1 114.20(8) 17_554 3_665 ? O1 Pr1 O1 65.80(8) 2_655 3_665 ? O1 Pr1 O1 114.20(8) 17_554 . ? O1 Pr1 O1 65.80(8) 2_655 . ? O1 Pr1 O1 65.80(8) 3_665 . ? O1 Pr1 O1 65.80(8) 17_554 18_544 ? O1 Pr1 O1 114.20(8) 2_655 18_544 ? O1 Pr1 O1 180.0 3_665 18_544 ? O1 Pr1 O1 114.20(8) . 18_544 ? O1 Pr1 O1 65.80(8) 17_554 16_654 ? O1 Pr1 O1 114.20(8) 2_655 16_654 ? O1 Pr1 O1 114.20(8) 3_665 16_654 ? O1 Pr1 O1 180.0 . 16_654 ? O1 Pr1 O1 65.80(8) 18_544 16_654 ? O1 Pr1 O2 48.92(8) 17_554 17_554 ? O1 Pr1 O2 131.09(8) 2_655 17_554 ? O1 Pr1 O2 71.39(8) 3_665 17_554 ? O1 Pr1 O2 76.02(9) . 17_554 ? O1 Pr1 O2 108.62(8) 18_544 17_554 ? O1 Pr1 O2 103.98(9) 16_654 17_554 ? O1 Pr1 O2 131.08(8) 17_554 2_655 ? O1 Pr1 O2 48.92(8) 2_655 2_655 ? O1 Pr1 O2 108.61(8) 3_665 2_655 ? O1 Pr1 O2 103.98(9) . 2_655 ? O1 Pr1 O2 71.38(8) 18_544 2_655 ? O1 Pr1 O2 76.02(9) 16_654 2_655 ? O2 Pr1 O2 180.0 17_554 2_655 ? O1 Pr1 O2 76.02(9) 17_554 3_665 ? O1 Pr1 O2 103.98(9) 2_655 3_665 ? O1 Pr1 O2 48.92(8) 3_665 3_665 ? O1 Pr1 O2 108.61(8) . 3_665 ? O1 Pr1 O2 131.08(8) 18_544 3_665 ? O1 Pr1 O2 71.39(8) 16_654 3_665 ? O2 Pr1 O2 60.168(8) 17_554 3_665 ? O2 Pr1 O2 119.831(8) 2_655 3_665 ? O1 Pr1 O2 71.39(8) 17_554 . ? O1 Pr1 O2 108.61(8) 2_655 . ? O1 Pr1 O2 103.98(9) 3_665 . ? O1 Pr1 O2 48.92(8) . . ? O1 Pr1 O2 76.02(9) 18_544 . ? O1 Pr1 O2 131.09(8) 16_654 . ? O2 Pr1 O2 60.169(8) 17_554 . ? O2 Pr1 O2 119.831(8) 2_655 . ? O2 Pr1 O2 119.831(8) 3_665 . ? O1 Pr1 O2 103.98(9) 17_554 18_544 ? O1 Pr1 O2 76.02(9) 2_655 18_544 ? O1 Pr1 O2 131.09(8) 3_665 18_544 ? O1 Pr1 O2 71.39(8) . 18_544 ? O1 Pr1 O2 48.91(8) 18_544 18_544 ? O1 Pr1 O2 108.61(8) 16_654 18_544 ? O2 Pr1 O2 119.834(8) 17_554 18_544 ? O2 Pr1 O2 60.166(8) 2_655 18_544 ? O2 Pr1 O2 180.0 3_665 18_544 ? O2 Pr1 O2 60.171(8) . 18_544 ? O1 Pr1 O2 108.61(8) 17_554 16_654 ? O1 Pr1 O2 71.38(8) 2_655 16_654 ? O1 Pr1 O2 76.02(9) 3_665 16_654 ? O1 Pr1 O2 131.09(8) . 16_654 ? O1 Pr1 O2 103.98(9) 18_544 16_654 ? O1 Pr1 O2 48.91(8) 16_654 16_654 ? O2 Pr1 O2 119.833(8) 17_554 16_654 ? O2 Pr1 O2 60.166(8) 2_655 16_654 ? O2 Pr1 O2 60.171(8) 3_665 16_654 ? O2 Pr1 O2 180.0 . 16_654 ? O2 Pr1 O2 119.826(8) 18_544 16_654 ? O1 Pr2 O1 71.24(8) 7_444 9_554 ? O1 Pr2 O1 71.23(8) 7_444 8_544 ? O1 Pr2 O1 71.23(8) 9_554 8_544 ? O1 Pr2 O4 152.76(8) 7_444 . ? O1 Pr2 O4 96.86(7) 9_554 . ? O1 Pr2 O4 129.31(8) 8_544 . ? O1 Pr2 O4 129.31(8) 7_444 3 ? O1 Pr2 O4 152.76(8) 9_554 3 ? O1 Pr2 O4 96.85(7) 8_544 3 ? O4 Pr2 O4 71.32(8) . 3 ? O1 Pr2 O4 96.86(7) 7_444 2 ? O1 Pr2 O4 129.31(8) 9_554 2 ? O1 Pr2 O4 152.76(8) 8_544 2 ? O4 Pr2 O4 71.32(8) . 2 ? O4 Pr2 O4 71.32(8) 3 2 ? O1 Pr2 O3 77.61(8) 7_444 2 ? O1 Pr2 O3 78.37(8) 9_554 2 ? O1 Pr2 O3 141.85(8) 8_544 2 ? O4 Pr2 O3 75.97(8) . 2 ? O4 Pr2 O3 120.12(8) 3 2 ? O4 Pr2 O3 51.01(7) 2 2 ? O1 Pr2 O3 141.85(8) 7_444 . ? O1 Pr2 O3 77.61(8) 9_554 . ? O1 Pr2 O3 78.36(8) 8_544 . ? O4 Pr2 O3 51.01(7) . . ? O4 Pr2 O3 75.97(8) 3 . ? O4 Pr2 O3 120.12(8) 2 . ? O3 Pr2 O3 117.28(3) 2 . ? O1 Pr2 O3 78.36(8) 7_444 3 ? O1 Pr2 O3 141.85(8) 9_554 3 ? O1 Pr2 O3 77.61(8) 8_544 3 ? O4 Pr2 O3 120.12(8) . 3 ? O4 Pr2 O3 51.01(7) 3 3 ? O4 Pr2 O3 75.97(8) 2 3 ? O3 Pr2 O3 117.28(3) 2 3 ? O3 Pr2 O3 117.28(3) . 3 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.235 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.088 data_z _database_code_depnum_ccdc_archive 'CCDC 915821' #TrackingRef 'CCDC-915821.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H14 N3 O7 Sm' _chemical_formula_sum 'C24 H14 N3 O7 Sm' _chemical_formula_weight 606.73 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd _symmetry_space_group_name_Hall '-F 2uv 2vw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 22.304(3) _cell_length_b 28.721(4) _cell_length_c 29.158(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 18678(4) _cell_formula_units_Z 32 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1095 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 14.78 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 9504 _exptl_absorpt_coefficient_mu 2.565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6023 _exptl_absorpt_correction_T_max 0.6696 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 23202 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4132 _reflns_number_gt 3327 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction SAINT-Plus _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0901P)^2^+183.3049P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4132 _refine_ls_number_parameters 322 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8396(5) 0.2545(4) 0.9720(4) 0.039(3) Uani 1 1 d . . . C2 C 0.8946(5) 0.2501(4) 1.0004(4) 0.040(3) Uani 1 1 d . . . C3 C 0.9386(6) 0.2189(5) 0.9887(5) 0.049(3) Uani 1 1 d . . . H3 H 0.9347 0.2013 0.9621 0.059 Uiso 1 1 calc R . . C4 C 0.9886(5) 0.2132(5) 1.0160(4) 0.045(3) Uani 1 1 d . . . H4 H 1.0184 0.1921 1.0076 0.054 Uiso 1 1 calc R . . C5 C 0.9945(5) 0.2387(4) 1.0558(4) 0.035(3) Uani 1 1 d . . . C6 C 0.9502(5) 0.2698(5) 1.0683(5) 0.047(3) Uani 1 1 d . . . H6 H 0.9536 0.2863 1.0957 0.057 Uiso 1 1 calc R . . C7 C 0.9009(6) 0.2764(5) 1.0404(4) 0.047(3) Uani 1 1 d . . . H7 H 0.8721 0.2984 1.0482 0.056 Uiso 1 1 calc R . . C8 C 1.0488(5) 0.2321(5) 1.0856(4) 0.040(3) Uani 1 1 d . . . C9 C 0.7561(5) 0.2938(5) 0.9506(4) 0.042(3) Uani 1 1 d . . . C10 C 0.7159(6) 0.3343(4) 0.9550(4) 0.040(3) Uani 1 1 d . . . C11 C 0.6631(6) 0.3360(5) 0.9301(4) 0.047(3) Uani 1 1 d . . . H11 H 0.6537 0.3117 0.9102 0.056 Uiso 1 1 calc R . . C12 C 0.6245(6) 0.3730(5) 0.9344(4) 0.047(3) Uani 1 1 d . . . H12 H 0.5893 0.3738 0.9173 0.057 Uiso 1 1 calc R . . C13 C 0.6376(6) 0.4090(4) 0.9637(4) 0.043(3) Uani 1 1 d . . . C14 C 0.6898(6) 0.4079(5) 0.9885(6) 0.063(4) Uani 1 1 d . . . H14 H 0.6992 0.4325 1.0079 0.076 Uiso 1 1 calc R . . C15 C 0.7288(6) 0.3705(5) 0.9848(5) 0.063(4) Uani 1 1 d . . . H15 H 0.7636 0.3697 1.0024 0.075 Uiso 1 1 calc R . . C16 C 0.5934(6) 0.4483(5) 0.9698(5) 0.047(3) Uani 1 1 d . . . C17 C 0.7771(5) 0.2238(4) 0.9189(4) 0.039(3) Uani 1 1 d . . . C18 C 0.7609(5) 0.1858(4) 0.8870(4) 0.035(3) Uani 1 1 d . . . C19 C 0.7113(5) 0.1900(4) 0.8581(4) 0.039(3) Uani 1 1 d . . . H19 H 0.6873 0.2164 0.8595 0.046 Uiso 1 1 calc R . . C20 C 0.6979(5) 0.1548(4) 0.8275(4) 0.036(3) Uani 1 1 d . . . H20 H 0.6647 0.1576 0.8084 0.043 Uiso 1 1 calc R . . C21 C 0.7336(5) 0.1150(4) 0.8249(4) 0.033(2) Uani 1 1 d . . . C22 C 0.7824(5) 0.1104(4) 0.8538(4) 0.041(3) Uani 1 1 d . . . H22 H 0.8061 0.0838 0.8525 0.049 Uiso 1 1 calc R . . C23 C 0.7961(5) 0.1452(4) 0.8847(4) 0.044(3) Uani 1 1 d . . . H23 H 0.8288 0.1418 0.9042 0.052 Uiso 1 1 calc R . . C24 C 0.7204(5) 0.0790(4) 0.7889(4) 0.037(3) Uani 1 1 d . . . N1 N 0.8052(4) 0.2917(4) 0.9773(4) 0.045(3) Uani 1 1 d . . . N2 N 0.8280(5) 0.2195(4) 0.9431(4) 0.041(3) Uani 1 1 d . . . N3 N 0.7402(4) 0.2604(3) 0.9214(4) 0.041(2) Uani 1 1 d . . . O1 O 1.0463(4) 0.2464(4) 1.1263(3) 0.050(2) Uani 1 1 d . . . O2 O 1.0939(4) 0.2119(4) 1.0681(3) 0.054(2) Uani 1 1 d . . . O3 O 0.5453(4) 0.4458(4) 0.9468(3) 0.055(3) Uani 1 1 d . . . O4 O 0.6069(4) 0.4805(3) 0.9967(4) 0.057(3) Uani 1 1 d . . . O5 O 0.7485(4) 0.0415(3) 0.7880(3) 0.045(2) Uani 1 1 d . . . O6 O 0.6818(4) 0.0887(3) 0.7583(3) 0.049(2) Uani 1 1 d . . . O1W O 1.1913(6) 0.1468(5) 1.0893(6) 0.118(6) Uani 1 1 d D . . Sm1 Sm 1.19544(2) 0.221721(19) 1.048105(19) 0.0304(3) Uani 1 1 d 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 C1 0.034(6) 0.043(7) 0.041(7) -0.012(6) -0.011(5) 0.005(5) C2 0.036(6) 0.041(7) 0.042(7) -0.009(5) -0.011(5) 0.009(5) C3 0.047(7) 0.061(9) 0.039(7) -0.018(6) -0.016(6) 0.009(6) C4 0.035(7) 0.060(9) 0.040(7) -0.009(6) -0.008(5) 0.012(6) C5 0.031(6) 0.050(7) 0.025(6) 0.002(5) -0.002(4) -0.004(5) C6 0.041(7) 0.062(9) 0.039(7) -0.018(6) -0.009(5) 0.003(6) C7 0.037(7) 0.058(9) 0.045(7) -0.018(6) -0.012(5) 0.010(6) C8 0.029(6) 0.060(8) 0.031(7) 0.003(6) 0.000(5) -0.001(5) C9 0.036(7) 0.042(7) 0.047(7) -0.015(6) -0.014(5) 0.005(6) C10 0.042(7) 0.038(7) 0.041(7) -0.014(5) -0.013(5) 0.009(6) C11 0.048(7) 0.044(7) 0.049(7) -0.018(6) -0.014(6) 0.014(6) C12 0.042(7) 0.052(8) 0.048(7) -0.009(6) -0.012(6) 0.010(6) C13 0.041(7) 0.043(7) 0.044(7) -0.010(6) 0.001(5) 0.011(6) C14 0.058(9) 0.055(9) 0.076(11) -0.034(8) -0.019(8) 0.022(7) C15 0.054(8) 0.062(10) 0.072(10) -0.034(8) -0.028(7) 0.021(7) C16 0.037(7) 0.051(8) 0.054(8) -0.010(7) 0.006(6) 0.009(6) C17 0.038(6) 0.039(7) 0.041(7) -0.010(5) -0.006(5) 0.005(5) C18 0.034(6) 0.034(6) 0.036(6) -0.010(5) -0.007(5) 0.002(5) C19 0.039(6) 0.032(6) 0.046(7) -0.013(5) -0.011(5) 0.012(5) C20 0.031(6) 0.040(7) 0.037(6) -0.007(5) -0.007(5) 0.003(5) C21 0.038(6) 0.029(6) 0.032(6) -0.003(5) -0.001(5) -0.004(5) C22 0.044(7) 0.031(6) 0.047(7) -0.011(5) -0.008(6) 0.013(5) C23 0.039(7) 0.042(7) 0.050(8) -0.007(6) -0.014(5) 0.011(5) C24 0.036(6) 0.032(7) 0.042(7) -0.006(5) 0.004(5) -0.005(5) N1 0.043(6) 0.040(6) 0.051(7) -0.017(5) -0.018(5) 0.011(5) N2 0.035(5) 0.043(6) 0.046(6) -0.014(5) -0.014(5) 0.009(5) N3 0.036(5) 0.041(6) 0.045(6) -0.016(5) -0.011(4) 0.012(5) O1 0.043(5) 0.080(7) 0.026(4) -0.005(4) -0.006(3) 0.007(4) O2 0.030(5) 0.092(8) 0.041(5) -0.003(5) -0.002(4) -0.002(5) O3 0.042(5) 0.065(7) 0.057(6) -0.014(5) -0.008(4) 0.023(5) O4 0.042(5) 0.056(6) 0.074(7) -0.026(5) -0.001(5) 0.015(4) O5 0.054(5) 0.030(4) 0.052(5) -0.007(4) 0.000(4) 0.008(4) O6 0.047(5) 0.048(5) 0.052(5) -0.022(4) -0.011(4) 0.009(4) O1W 0.141(12) 0.066(9) 0.146(15) 0.044(9) 0.046(10) -0.001(8) Sm1 0.0315(4) 0.0283(4) 0.0314(4) -0.0015(2) 0.0033(2) 0.0014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 N1 1.325(15) . ? C1 N2 1.336(15) . ? C1 C2 1.485(15) . ? C2 C3 1.373(17) . ? C2 C7 1.398(17) . ? C3 C4 1.380(16) . ? C3 H3 0.9300 . ? C4 C5 1.379(17) . ? C4 H4 0.9300 . ? C5 C6 1.379(17) . ? C5 C8 1.503(16) . ? C6 C7 1.381(17) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O1 1.256(15) . ? C8 O2 1.268(15) . ? C9 N3 1.331(15) . ? C9 N1 1.345(15) . ? C9 C10 1.475(17) . ? C10 C11 1.384(17) . ? C10 C15 1.385(17) . ? C11 C12 1.375(17) . ? C11 H11 0.9300 . ? C12 C13 1.372(17) . ? C12 H12 0.9300 . ? C13 C14 1.369(18) . ? C13 C16 1.510(17) . ? C14 C15 1.386(19) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O4 1.249(16) . ? C16 O3 1.267(16) . ? C17 N2 1.343(15) . ? C17 N3 1.337(15) . ? C17 C18 1.479(16) . ? C18 C19 1.396(15) . ? C18 C23 1.407(16) . ? C19 C20 1.382(16) . ? C19 H19 0.9300 . ? C20 C21 1.395(16) . ? C20 H20 0.9300 . ? C21 C22 1.384(16) . ? C21 C24 1.502(16) . ? C22 C23 1.380(17) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 O5 1.246(14) . ? C24 O6 1.271(15) . ? O1 Sm1 2.324(9) 11_656 ? O2 Sm1 2.356(9) . ? O3 Sm1 2.353(9) 18_567 ? O4 Sm1 2.344(9) 2_655 ? O5 Sm1 2.380(8) 24_755 ? O5 Sm1 2.802(9) 16_446 ? O6 Sm1 2.411(8) 16_446 ? O1W Sm1 2.468(13) . ? Sm1 O1 2.324(9) 11_656 ? Sm1 O4 2.344(9) 2_655 ? Sm1 O3 2.353(9) 30_657 ? Sm1 O5 2.380(8) 20_766 ? Sm1 O6 2.411(8) 16_546 ? Sm1 O5 2.802(9) 16_546 ? 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 N1 C1 N2 124.6(10) . . ? N1 C1 C2 118.8(10) . . ? N2 C1 C2 116.6(10) . . ? C3 C2 C7 119.2(11) . . ? C3 C2 C1 120.5(11) . . ? C7 C2 C1 120.2(10) . . ? C2 C3 C4 120.8(12) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 119.9(12) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.9(11) . . ? C6 C5 C8 120.3(11) . . ? C4 C5 C8 119.7(11) . . ? C5 C6 C7 120.2(12) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 119.8(12) . . ? C6 C7 H7 120.1 . . ? C2 C7 H7 120.1 . . ? O1 C8 O2 124.4(11) . . ? O1 C8 C5 117.9(11) . . ? O2 C8 C5 117.6(11) . . ? N3 C9 N1 123.8(11) . . ? N3 C9 C10 117.5(10) . . ? N1 C9 C10 118.6(10) . . ? C11 C10 C15 118.6(12) . . ? C11 C10 C9 119.9(11) . . ? C15 C10 C9 121.5(11) . . ? C10 C11 C12 120.7(12) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 120.4(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 119.5(12) . . ? C14 C13 C16 120.7(12) . . ? C12 C13 C16 119.8(11) . . ? C13 C14 C15 120.6(13) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C10 C15 C14 120.1(12) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 120.0 . . ? O4 C16 O3 125.3(12) . . ? O4 C16 C13 118.0(12) . . ? O3 C16 C13 116.7(12) . . ? N2 C17 N3 124.4(11) . . ? N2 C17 C18 118.0(10) . . ? N3 C17 C18 117.6(10) . . ? C19 C18 C23 119.0(10) . . ? C19 C18 C17 120.7(10) . . ? C23 C18 C17 120.3(10) . . ? C20 C19 C18 119.9(10) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 120.7(10) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 119.6(10) . . ? C22 C21 C24 121.0(10) . . ? C20 C21 C24 119.3(10) . . ? C21 C22 C23 120.2(11) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C18 120.5(11) . . ? C22 C23 H23 119.7 . . ? C18 C23 H23 119.8 . . ? O5 C24 O6 121.1(11) . . ? O5 C24 C21 120.7(11) . . ? O6 C24 C21 118.1(10) . . ? O5 C24 Sm1 69.8(7) . 16_446 ? O6 C24 Sm1 51.9(6) . 16_446 ? C21 C24 Sm1 165.6(8) . 16_446 ? C1 N1 C9 116.1(10) . . ? C17 N2 C1 115.2(10) . . ? C9 N3 C17 115.9(10) . . ? C8 O1 Sm1 142.4(9) . 11_656 ? C8 O2 Sm1 143.9(9) . . ? C16 O3 Sm1 138.6(8) . 18_567 ? C16 O4 Sm1 135.7(8) . 2_655 ? C24 O5 Sm1 171.6(8) . 24_755 ? C24 O5 Sm1 85.6(7) . 16_446 ? Sm1 O5 Sm1 102.6(3) 24_755 16_446 ? C24 O6 Sm1 103.6(7) . 16_446 ? O1 Sm1 O4 117.8(4) 11_656 2_655 ? O1 Sm1 O3 87.8(3) 11_656 30_657 ? O4 Sm1 O3 134.2(3) 2_655 30_657 ? O1 Sm1 O2 83.0(3) 11_656 . ? O4 Sm1 O2 75.5(3) 2_655 . ? O3 Sm1 O2 149.0(4) 30_657 . ? O1 Sm1 O5 79.5(3) 11_656 20_766 ? O4 Sm1 O5 71.9(3) 2_655 20_766 ? O3 Sm1 O5 77.1(3) 30_657 20_766 ? O2 Sm1 O5 129.5(3) . 20_766 ? O1 Sm1 O6 151.3(4) 11_656 16_546 ? O4 Sm1 O6 85.6(4) 2_655 16_546 ? O3 Sm1 O6 86.3(3) 30_657 16_546 ? O2 Sm1 O6 87.8(3) . 16_546 ? O5 Sm1 O6 126.0(3) 20_766 16_546 ? O1 Sm1 O1W 78.9(5) 11_656 . ? O4 Sm1 O1W 143.5(5) 2_655 . ? O3 Sm1 O1W 74.3(4) 30_657 . ? O2 Sm1 O1W 74.9(4) . . ? O5 Sm1 O1W 144.5(5) 20_766 . ? O6 Sm1 O1W 72.5(5) 16_546 . ? O1 Sm1 O5 149.1(3) 11_656 16_546 ? O4 Sm1 O5 73.6(3) 2_655 16_546 ? O3 Sm1 O5 67.3(3) 30_657 16_546 ? O2 Sm1 O5 127.7(3) . 16_546 ? O5 Sm1 O5 77.4(3) 20_766 16_546 ? O6 Sm1 O5 49.0(3) 16_546 16_546 ? O1W Sm1 O5 109.5(4) . 16_546 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.815 _refine_diff_density_min -1.503 _refine_diff_density_rms 0.147