# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # 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_UCY-4 _database_code_depnum_ccdc_archive 'CCDC 916221' #TrackingRef 'UCY-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 La N3 O8' _chemical_formula_sum 'C22 H20 La N3 O8' _chemical_formula_weight 593.32 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' La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.0739(10) _cell_length_b 14.5356(5) _cell_length_c 13.5095(5) _cell_angle_alpha 90.0 _cell_angle_beta 100.097(5) _cell_angle_gamma 90.0 _cell_volume 5620.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5672 _cell_measurement_theta_min 2.9807 _cell_measurement_theta_max 25.0628 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2352 _exptl_absorpt_coefficient_mu 1.563 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72619 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12896 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4946 _reflns_number_gt 4306 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0883P)^2^+21.2011P] 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 4946 _refine_ls_number_parameters 311 _refine_ls_number_restraints 77 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1485 _refine_ls_wR_factor_gt 0.1438 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.112 _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 La1 La 0.319192(9) 0.214354(19) 0.54329(2) 0.03235(16) Uani 1 1 d . . . O1 O 0.39617(14) 0.1834(3) 0.4880(4) 0.0617(13) Uani 1 1 d . . . O2 O 0.38215(14) 0.3310(3) 0.5015(4) 0.0533(11) Uani 1 1 d . . . O3 O 0.29421(12) 0.0667(3) 0.4462(3) 0.0447(10) Uani 1 1 d . . . O4 O 0.23180(12) 0.1481(2) 0.4627(3) 0.0399(9) Uani 1 1 d . . . O5 O 0.29710(13) 0.2601(3) 0.3652(3) 0.0455(9) Uani 1 1 d . . . O6 O 0.27278(13) 0.1744(4) 0.6768(3) 0.0560(12) Uani 1 1 d . . . O7 O 0.35934(19) 0.0832(4) 0.6480(5) 0.0780(14) Uani 1 1 d U . . O8 O 0.3615(2) 0.2858(4) 0.7000(5) 0.0805(17) Uani 1 1 d U . . N1 N 0.59992(15) 0.4182(4) 0.3513(4) 0.0465(12) Uani 1 1 d . . . N2 N 0.3841(3) 0.0153(7) 0.8106(7) 0.106(2) Uani 1 1 d U . . N3 N 0.3826(4) 0.3863(8) 0.8285(8) 0.130(3) Uani 1 1 d U . . C1 C 0.40701(19) 0.2668(4) 0.4806(5) 0.0442(14) Uani 1 1 d . . . C2 C 0.4521(2) 0.2865(4) 0.4447(5) 0.0471(15) Uani 1 1 d . . . C3 C 0.4813(3) 0.2149(5) 0.4260(8) 0.075(3) Uani 1 1 d . . . H3 H 0.4729 0.1543 0.4359 0.090 Uiso 1 1 calc R . . C4 C 0.5226(3) 0.2336(5) 0.3928(8) 0.080(3) Uani 1 1 d . . . H4 H 0.5414 0.1854 0.3784 0.097 Uiso 1 1 calc R . . C5 C 0.5361(2) 0.3231(5) 0.3809(5) 0.0541(16) Uani 1 1 d . . . C6 C 0.5083(2) 0.3944(5) 0.4009(6) 0.0605(18) Uani 1 1 d . . . H6 H 0.5174 0.4549 0.3935 0.073 Uiso 1 1 calc R . . C7 C 0.4661(2) 0.3754(5) 0.4325(6) 0.0591(18) Uani 1 1 d . . . H7 H 0.4471 0.4237 0.4456 0.071 Uiso 1 1 calc R . . C8 C 0.5830(2) 0.3393(5) 0.3562(6) 0.0569(17) Uani 1 1 d D . . H16 H 0.605(3) 0.290(5) 0.351(8) 0.12(4) Uiso 1 1 d D . . C9 C 0.25119(17) 0.0769(3) 0.4306(4) 0.0363(12) Uani 1 1 d . . . C10 C 0.22054(17) 0.0048(4) 0.3736(4) 0.0367(12) Uani 1 1 d . . . C11 C 0.17373(17) -0.0029(4) 0.3832(5) 0.0406(13) Uani 1 1 d . . . H11 H 0.1606 0.0389 0.4223 0.049 Uiso 1 1 calc R . . C12 C 0.14661(18) -0.0743(4) 0.3330(4) 0.0403(12) Uani 1 1 d . . . C13 C 0.16476(17) -0.1310(4) 0.2676(4) 0.0375(12) Uani 1 1 d . . . H13 H 0.1459 -0.1753 0.2311 0.045 Uiso 1 1 calc R . . C14 C 0.21171(17) -0.1219(4) 0.2559(4) 0.0371(12) Uani 1 1 d . . . C15 C 0.23962(17) -0.0547(4) 0.3111(4) 0.0377(12) Uani 1 1 d . . . H15 H 0.2710 -0.0498 0.3060 0.045 Uiso 1 1 calc R . . C16 C 0.26944(19) 0.3167(4) 0.3157(4) 0.0423(13) Uani 1 1 d . . . C17 C 0.3687(4) 0.0890(9) 0.7503(9) 0.114(3) Uani 1 1 d U . . C18 C 0.3767(6) -0.0763(10) 0.7537(13) 0.163(4) Uani 1 1 d U . . H18A H 0.3878 -0.1259 0.7985 0.245 Uiso 1 1 calc R . . H18B H 0.3936 -0.0757 0.6987 0.245 Uiso 1 1 calc R . . H18C H 0.3440 -0.0847 0.7282 0.245 Uiso 1 1 calc R . . C19 C 0.3977(5) 0.0270(10) 0.9191(9) 0.132(3) Uani 1 1 d U . . H19A H 0.4075 -0.0312 0.9494 0.199 Uiso 1 1 calc R . . H19B H 0.3716 0.0497 0.9465 0.199 Uiso 1 1 calc R . . H19C H 0.4231 0.0701 0.9328 0.199 Uiso 1 1 calc R . . C20 C 0.3498(5) 0.3246(11) 0.7601(11) 0.125(3) Uani 1 1 d U . . C21 C 0.3665(5) 0.4354(10) 0.9006(11) 0.138(4) Uani 1 1 d U . . H21A H 0.3911 0.4731 0.9358 0.207 Uiso 1 1 calc R . . H21B H 0.3558 0.3940 0.9471 0.207 Uiso 1 1 calc R . . H21C H 0.3410 0.4738 0.8700 0.207 Uiso 1 1 calc R . . C22 C 0.4287(5) 0.3986(10) 0.8009(11) 0.144(4) Uani 1 1 d U . . H22A H 0.4322 0.3566 0.7479 0.215 Uiso 1 1 calc R . . H22B H 0.4525 0.3867 0.8583 0.215 Uiso 1 1 calc R . . H22C H 0.4317 0.4606 0.7783 0.215 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 La1 0.0203(2) 0.0318(2) 0.0491(2) 0.00183(11) 0.01779(15) -0.00072(10) O1 0.034(2) 0.047(3) 0.114(4) 0.000(3) 0.041(2) 0.001(2) O2 0.037(2) 0.047(2) 0.085(3) -0.010(2) 0.036(2) -0.0089(18) O3 0.0265(18) 0.037(2) 0.075(3) -0.0075(19) 0.0206(18) -0.0020(15) O4 0.0298(18) 0.0331(19) 0.062(2) -0.0033(17) 0.0241(17) -0.0028(15) O5 0.036(2) 0.055(2) 0.052(2) 0.008(2) 0.0224(18) 0.0046(19) O6 0.029(2) 0.083(3) 0.062(3) 0.028(2) 0.0232(19) 0.007(2) O7 0.060(3) 0.082(3) 0.092(3) 0.012(3) 0.015(2) 0.027(2) O8 0.085(3) 0.086(3) 0.070(3) 0.005(2) 0.010(3) -0.014(3) N1 0.028(2) 0.055(3) 0.062(3) -0.010(2) 0.023(2) -0.011(2) N2 0.105(4) 0.108(4) 0.103(3) 0.017(3) 0.015(3) 0.002(4) N3 0.141(4) 0.121(5) 0.126(5) -0.014(4) 0.018(4) -0.001(4) C1 0.028(3) 0.051(3) 0.058(4) -0.006(3) 0.019(3) -0.005(3) C2 0.031(3) 0.052(4) 0.063(4) -0.008(3) 0.022(3) -0.011(2) C3 0.050(4) 0.046(4) 0.143(8) -0.002(4) 0.059(5) -0.004(3) C4 0.055(4) 0.053(4) 0.148(9) -0.018(5) 0.057(5) -0.006(3) C5 0.049(3) 0.050(4) 0.072(4) -0.014(3) 0.034(3) -0.011(3) C6 0.048(4) 0.047(4) 0.094(5) -0.012(4) 0.035(4) -0.010(3) C7 0.042(3) 0.055(4) 0.087(5) -0.012(3) 0.029(3) -0.006(3) C8 0.042(3) 0.059(4) 0.077(5) -0.011(3) 0.031(3) -0.005(3) C9 0.032(3) 0.026(2) 0.057(3) -0.002(2) 0.023(2) -0.002(2) C10 0.029(2) 0.032(3) 0.053(3) 0.002(2) 0.019(2) -0.001(2) C11 0.030(3) 0.036(3) 0.063(4) 0.000(3) 0.027(2) -0.002(2) C12 0.028(3) 0.046(3) 0.053(3) -0.003(3) 0.022(2) -0.001(2) C13 0.031(3) 0.036(3) 0.050(3) -0.002(2) 0.021(2) -0.006(2) C14 0.029(3) 0.040(3) 0.048(3) 0.000(2) 0.021(2) -0.002(2) C15 0.022(2) 0.042(3) 0.053(3) 0.002(2) 0.018(2) 0.001(2) C16 0.033(3) 0.052(3) 0.048(3) 0.007(3) 0.022(2) 0.003(3) C17 0.106(5) 0.129(4) 0.109(4) 0.020(4) 0.018(4) 0.003(4) C18 0.178(6) 0.145(4) 0.170(6) -0.022(4) 0.036(5) 0.002(5) C19 0.138(6) 0.139(5) 0.118(4) 0.014(4) 0.015(4) -0.001(4) C20 0.132(5) 0.127(5) 0.119(5) -0.008(4) 0.028(4) 0.007(4) C21 0.148(6) 0.136(6) 0.127(5) -0.011(4) 0.019(4) 0.004(4) C22 0.140(4) 0.143(6) 0.147(6) 0.000(5) 0.021(4) 0.001(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 La1 O5 2.470(4) . ? La1 O8 2.481(6) . ? La1 O4 2.482(4) 7_556 ? La1 O6 2.502(4) . ? La1 O1 2.521(4) . ? La1 O7 2.534(5) . ? La1 O3 2.553(4) . ? La1 O2 2.628(4) . ? La1 O4 2.757(4) . ? La1 C1 2.928(6) . ? La1 C9 3.027(5) . ? La1 La1 4.1206(8) 7_556 ? O1 C1 1.261(8) . ? O2 C1 1.243(7) . ? O3 C9 1.240(6) . ? O4 C9 1.289(6) . ? O4 La1 2.482(4) 7_556 ? O5 C16 1.257(7) . ? O6 C16 1.256(7) 7_556 ? O7 C17 1.363(13) . ? O8 C20 1.091(15) . ? N1 C8 1.254(8) . ? N1 C12 1.426(7) 3 ? N2 C17 1.373(14) . ? N2 C19 1.460(14) . ? N2 C18 1.534(16) . ? N3 C21 1.356(16) . ? N3 C22 1.463(17) . ? N3 C20 1.503(17) . ? C1 C2 1.504(8) . ? C2 C7 1.373(9) . ? C2 C3 1.393(9) . ? C3 C4 1.381(10) . ? C3 H3 0.9300 . ? C4 C5 1.377(10) . ? C4 H4 0.9300 . ? C5 C6 1.370(9) . ? C5 C8 1.478(8) . ? C6 C7 1.395(9) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H16 0.96(2) . ? C9 C10 1.499(7) . ? C10 C15 1.390(8) . ? C10 C11 1.394(7) . ? C11 C12 1.404(8) . ? C11 H11 0.9300 . ? C12 C13 1.379(8) . ? C12 N1 1.426(7) 3_445 ? C13 C14 1.408(7) . ? C13 H13 0.9300 . ? C14 C15 1.399(8) . ? C14 C16 1.490(8) 4_545 ? C15 H15 0.9300 . ? C16 O6 1.256(7) 7_556 ? C16 C14 1.490(8) 4 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O5 La1 O8 136.36(17) . . ? O5 La1 O4 72.53(14) . 7_556 ? O8 La1 O4 83.93(18) . 7_556 ? O5 La1 O6 133.11(13) . . ? O8 La1 O6 74.4(2) . . ? O4 La1 O6 79.38(14) 7_556 . ? O5 La1 O1 81.49(16) . . ? O8 La1 O1 89.7(2) . . ? O4 La1 O1 133.66(14) 7_556 . ? O6 La1 O1 142.28(16) . . ? O5 La1 O7 139.65(17) . . ? O8 La1 O7 74.20(19) . . ? O4 La1 O7 146.96(16) 7_556 . ? O6 La1 O7 71.15(16) . . ? O1 La1 O7 71.66(18) . . ? O5 La1 O3 73.96(15) . . ? O8 La1 O3 147.53(16) . . ? O4 La1 O3 123.08(12) 7_556 . ? O6 La1 O3 91.99(15) . . ? O1 La1 O3 83.40(14) . . ? O7 La1 O3 73.52(18) . . ? O5 La1 O2 71.88(15) . . ? O8 La1 O2 69.75(18) . . ? O4 La1 O2 84.71(12) 7_556 . ? O6 La1 O2 142.02(16) . . ? O1 La1 O2 50.47(14) . . ? O7 La1 O2 109.60(17) . . ? O3 La1 O2 125.31(13) . . ? O5 La1 O4 69.20(13) . . ? O8 La1 O4 140.13(19) . . ? O4 La1 O4 76.38(12) 7_556 . ? O6 La1 O4 68.14(13) . . ? O1 La1 O4 128.70(14) . . ? O7 La1 O4 105.09(16) . . ? O3 La1 O4 49.01(11) . . ? O2 La1 O4 140.26(14) . . ? O5 La1 C1 74.88(16) . . ? O8 La1 C1 79.1(2) . . ? O4 La1 C1 109.10(15) 7_556 . ? O6 La1 C1 151.21(16) . . ? O1 La1 C1 25.37(16) . . ? O7 La1 C1 91.02(18) . . ? O3 La1 C1 104.72(15) . . ? O2 La1 C1 25.11(15) . . ? O4 La1 C1 140.06(15) . . ? O5 La1 C9 69.66(15) . . ? O8 La1 C9 152.54(18) . . ? O4 La1 C9 100.45(13) 7_556 . ? O6 La1 C9 79.76(15) . . ? O1 La1 C9 105.59(15) . . ? O7 La1 C9 88.89(18) . . ? O3 La1 C9 23.80(12) . . ? O2 La1 C9 137.39(14) . . ? O4 La1 C9 25.21(12) . . ? C1 La1 C9 123.51(16) . . ? O5 La1 La1 65.27(9) . 7_556 ? O8 La1 La1 116.73(17) . 7_556 ? O4 La1 La1 40.55(8) 7_556 7_556 ? O6 La1 La1 68.89(9) . 7_556 ? O1 La1 La1 146.52(13) . 7_556 ? O7 La1 La1 132.76(13) . 7_556 ? O3 La1 La1 83.68(8) . 7_556 ? O2 La1 La1 117.32(10) . 7_556 ? O4 La1 La1 35.82(8) . 7_556 ? C1 La1 La1 135.23(13) . 7_556 ? C9 La1 La1 60.26(10) . 7_556 ? C1 O1 La1 95.7(3) . . ? C1 O2 La1 91.1(3) . . ? C9 O3 La1 100.0(3) . . ? C9 O4 La1 158.4(4) . 7_556 ? C9 O4 La1 89.2(3) . . ? La1 O4 La1 103.62(12) 7_556 . ? C16 O5 La1 136.6(4) . . ? C16 O6 La1 133.8(4) 7_556 . ? C17 O7 La1 120.6(6) . . ? C20 O8 La1 132.8(10) . . ? C8 N1 C12 118.3(5) . 3 ? C17 N2 C19 120.5(11) . . ? C17 N2 C18 112.2(10) . . ? C19 N2 C18 126.5(11) . . ? C21 N3 C22 124.5(12) . . ? C21 N3 C20 119.5(12) . . ? C22 N3 C20 115.3(12) . . ? O2 C1 O1 122.7(5) . . ? O2 C1 C2 120.3(5) . . ? O1 C1 C2 116.9(5) . . ? O2 C1 La1 63.8(3) . . ? O1 C1 La1 58.9(3) . . ? C2 C1 La1 175.5(4) . . ? C7 C2 C3 118.7(6) . . ? C7 C2 C1 120.7(6) . . ? C3 C2 C1 120.6(5) . . ? C4 C3 C2 120.2(6) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.4(7) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C6 C5 C4 120.1(6) . . ? C6 C5 C8 121.6(6) . . ? C4 C5 C8 118.0(6) . . ? C5 C6 C7 119.5(6) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C2 C7 C6 121.1(6) . . ? C2 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? N1 C8 C5 123.0(6) . . ? N1 C8 H16 114(6) . . ? C5 C8 H16 122(6) . . ? O3 C9 O4 121.8(5) . . ? O3 C9 C10 119.6(5) . . ? O4 C9 C10 118.6(4) . . ? O3 C9 La1 56.2(3) . . ? O4 C9 La1 65.6(3) . . ? C10 C9 La1 175.8(3) . . ? C15 C10 C11 120.5(5) . . ? C15 C10 C9 118.9(4) . . ? C11 C10 C9 120.7(5) . . ? C10 C11 C12 119.3(5) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 120.3(5) . . ? C13 C12 N1 123.3(5) . 3_445 ? C11 C12 N1 116.4(5) . 3_445 ? C12 C13 C14 120.3(5) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.3(5) . . ? C15 C14 C16 121.3(5) . 4_545 ? C13 C14 C16 119.4(5) . 4_545 ? C10 C15 C14 120.1(5) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? O6 C16 O5 124.6(5) 7_556 . ? O6 C16 C14 117.8(5) 7_556 4 ? O5 C16 C14 117.6(5) . 4 ? O7 C17 N2 122.6(11) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 C20 N3 121.3(14) . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.991 _refine_diff_density_min -0.882 _refine_diff_density_rms 0.128 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.497 0.001 1468 182 ' ' data_UCY-5 _database_code_depnum_ccdc_archive 'CCDC 916222' #TrackingRef 'UCY-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 Ce N3 O8' _chemical_formula_sum 'C22 H20 Ce N3 O8' _chemical_formula_weight 594.53 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.0489(12) _cell_length_b 14.5685(6) _cell_length_c 13.5097(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.119(5) _cell_angle_gamma 90.00 _cell_volume 5628.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8278 _cell_measurement_theta_min 2.9824 _cell_measurement_theta_max 28.5980 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2360 _exptl_absorpt_coefficient_mu 1.661 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.77726 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14490 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 26.74 _reflns_number_total 5942 _reflns_number_gt 4693 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0582P)^2^+82.7452P] 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 5942 _refine_ls_number_parameters 310 _refine_ls_number_restraints 82 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1493 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.077 _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 Ce1 Ce 0.318677(11) 0.21403(2) 0.04279(3) 0.02804(14) Uani 1 1 d . . . O1 O 0.38127(17) 0.3309(4) 0.0018(5) 0.0489(14) Uani 1 1 d . . . O2 O 0.39513(18) 0.1838(4) -0.0122(6) 0.0579(17) Uani 1 1 d . . . O3 O 0.27290(17) 0.1734(4) 0.1744(4) 0.0515(15) Uani 1 1 d . . . O4 O 0.29748(17) 0.2605(4) -0.1345(4) 0.0409(12) Uani 1 1 d . . . O5 O 0.29442(16) 0.0681(3) -0.0547(4) 0.0408(12) Uani 1 1 d . . . O6 O 0.26837(16) 0.3515(3) 0.0372(4) 0.0372(11) Uani 1 1 d . . . O7 O 0.3609(3) 0.2845(5) 0.1963(6) 0.0744(19) Uani 1 1 d DU . . O8 O 0.3586(2) 0.0827(5) 0.1471(6) 0.0721(18) Uani 1 1 d DU . . N1 N 0.5992(2) 0.4185(5) -0.1501(5) 0.0418(15) Uani 1 1 d . . . N2 N 0.3826(4) 0.3840(9) 0.3285(10) 0.124(4) Uani 1 1 d DU . . N3 N 0.3832(4) 0.0130(7) 0.3105(8) 0.100(3) Uani 1 1 d DU . . C1 C 0.4060(2) 0.2669(5) -0.0192(6) 0.0381(17) Uani 1 1 d . . . C2 C 0.4517(2) 0.2862(5) -0.0541(6) 0.0400(17) Uani 1 1 d . . . C3 C 0.4801(3) 0.2153(6) -0.0746(9) 0.065(3) Uani 1 1 d . . . H3 H 0.4707 0.1549 -0.0681 0.078 Uiso 1 1 calc R . . C4 C 0.5228(3) 0.2329(7) -0.1049(11) 0.083(4) Uani 1 1 d . . . H4 H 0.5418 0.1844 -0.1174 0.099 Uiso 1 1 calc R . . C5 C 0.5367(3) 0.3214(6) -0.1164(7) 0.051(2) Uani 1 1 d . . . C6 C 0.5077(3) 0.3948(6) -0.0996(8) 0.055(2) Uani 1 1 d . . . H6 H 0.5165 0.4551 -0.1092 0.066 Uiso 1 1 calc R . . C7 C 0.4648(3) 0.3749(6) -0.0675(7) 0.054(2) Uani 1 1 d . . . H7 H 0.4453 0.4228 -0.0555 0.065 Uiso 1 1 calc R . . C8 C 0.5828(3) 0.3396(6) -0.1456(7) 0.049(2) Uani 1 1 d D . . C9 C 0.2305(2) 0.1817(5) 0.1834(6) 0.0393(17) Uani 1 1 d . . . C10 C 0.2114(2) 0.1213(5) 0.2554(5) 0.0336(15) Uani 1 1 d . . . C11 C 0.1648(2) 0.1314(5) 0.2672(5) 0.0345(15) Uani 1 1 d . . . H11 H 0.1462 0.1765 0.2316 0.041 Uiso 1 1 calc R . . C12 C 0.1463(2) 0.0733(5) 0.3327(6) 0.0355(16) Uani 1 1 d . . . C13 C 0.1737(2) 0.0025(5) 0.3837(6) 0.0354(16) Uani 1 1 d . . . H13 H 0.1607 -0.0382 0.4241 0.043 Uiso 1 1 calc R . . C14 C 0.2203(2) -0.0061(4) 0.3730(5) 0.0313(14) Uani 1 1 d . . . C15 C 0.2392(2) 0.0543(5) 0.3098(5) 0.0325(15) Uani 1 1 d . . . H15 H 0.2706 0.0495 0.3042 0.039 Uiso 1 1 calc R . . C16 C 0.2508(2) 0.0784(4) -0.0710(5) 0.0314(14) Uani 1 1 d . . . C17 C 0.3479(5) 0.3272(11) 0.2662(10) 0.127(4) Uani 1 1 d DU . . C18 C 0.3614(6) 0.4361(12) 0.3997(12) 0.141(5) Uani 1 1 d DU . . H18A H 0.3305 0.4132 0.4004 0.212 Uiso 1 1 calc R . . H18B H 0.3597 0.4996 0.3805 0.212 Uiso 1 1 calc R . . H18C H 0.3800 0.4300 0.4656 0.212 Uiso 1 1 calc R . . C19 C 0.4285(5) 0.3974(12) 0.3023(13) 0.134(5) Uani 1 1 d DU . . H19A H 0.4332 0.3534 0.2521 0.202 Uiso 1 1 calc R . . H19B H 0.4520 0.3895 0.3610 0.202 Uiso 1 1 calc R . . H19C H 0.4305 0.4583 0.2762 0.202 Uiso 1 1 calc R . . C20 C 0.3674(5) 0.0870(9) 0.2412(6) 0.109(4) Uani 1 1 d DU . . C21 C 0.3778(7) -0.0723(10) 0.2534(13) 0.148(5) Uani 1 1 d DU . . H21A H 0.3881 -0.1228 0.2975 0.223 Uiso 1 1 calc R . . H21B H 0.3963 -0.0697 0.2012 0.223 Uiso 1 1 calc R . . H21C H 0.3455 -0.0807 0.2241 0.223 Uiso 1 1 calc R . . C22 C 0.3988(6) 0.0256(13) 0.4177(9) 0.140(6) Uani 1 1 d DU . . H22A H 0.4076 -0.0326 0.4485 0.210 Uiso 1 1 calc R . . H22B H 0.3738 0.0515 0.4468 0.210 Uiso 1 1 calc R . . H22C H 0.4251 0.0664 0.4287 0.210 Uiso 1 1 calc R . . H16 H 0.592(6) 0.274(3) -0.151(14) 0.168 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 Ce1 0.01934(19) 0.0255(2) 0.0431(2) 0.00092(17) 0.01615(15) -0.00100(13) O1 0.035(3) 0.039(3) 0.082(4) -0.013(3) 0.035(3) -0.013(2) O2 0.038(3) 0.039(3) 0.109(5) 0.000(3) 0.048(3) -0.002(2) O3 0.028(3) 0.071(4) 0.060(4) 0.029(3) 0.022(2) 0.006(3) O4 0.032(3) 0.049(3) 0.047(3) 0.008(3) 0.019(2) 0.004(2) O5 0.026(2) 0.029(2) 0.072(4) -0.008(2) 0.021(2) -0.0024(19) O6 0.031(2) 0.026(2) 0.060(3) -0.004(2) 0.023(2) -0.0030(19) O7 0.080(4) 0.072(4) 0.070(3) 0.008(3) 0.009(3) -0.015(3) O8 0.057(3) 0.080(4) 0.080(3) 0.005(3) 0.012(3) 0.020(3) N1 0.028(3) 0.050(4) 0.053(4) -0.005(3) 0.022(3) -0.009(3) N2 0.129(5) 0.117(5) 0.121(5) -0.008(4) 0.011(4) -0.002(4) N3 0.101(5) 0.101(5) 0.099(4) 0.009(4) 0.017(4) 0.002(4) C1 0.024(3) 0.041(4) 0.055(5) -0.003(3) 0.021(3) -0.003(3) C2 0.025(3) 0.047(4) 0.052(4) -0.005(4) 0.019(3) -0.009(3) C3 0.046(5) 0.044(5) 0.116(9) -0.002(5) 0.048(5) -0.002(4) C4 0.049(5) 0.055(6) 0.161(12) -0.022(7) 0.064(7) -0.007(4) C5 0.039(4) 0.052(5) 0.069(6) -0.020(4) 0.030(4) -0.015(4) C6 0.042(4) 0.044(5) 0.086(7) -0.009(5) 0.032(4) -0.010(4) C7 0.041(4) 0.045(5) 0.083(6) -0.008(4) 0.031(4) -0.002(4) C8 0.039(4) 0.054(5) 0.061(5) -0.010(4) 0.029(4) -0.008(4) C9 0.032(4) 0.040(4) 0.051(4) 0.007(4) 0.021(3) 0.006(3) C10 0.030(3) 0.032(3) 0.043(4) 0.000(3) 0.019(3) -0.001(3) C11 0.028(3) 0.036(4) 0.044(4) 0.005(3) 0.016(3) 0.005(3) C12 0.024(3) 0.035(4) 0.052(4) 0.000(3) 0.020(3) 0.001(3) C13 0.028(3) 0.028(3) 0.056(4) 0.003(3) 0.021(3) -0.001(3) C14 0.029(3) 0.021(3) 0.048(4) 0.002(3) 0.020(3) 0.001(2) C15 0.019(3) 0.035(4) 0.048(4) 0.000(3) 0.017(3) -0.001(3) C16 0.028(3) 0.024(3) 0.046(4) -0.002(3) 0.019(3) -0.002(3) C17 0.129(6) 0.126(6) 0.127(6) -0.006(4) 0.023(4) 0.003(4) C18 0.147(6) 0.141(7) 0.135(6) -0.005(4) 0.026(5) 0.003(5) C19 0.135(5) 0.132(7) 0.135(7) 0.002(5) 0.021(4) 0.002(4) C20 0.106(6) 0.116(5) 0.104(5) 0.009(4) 0.019(4) 0.000(4) C21 0.158(7) 0.137(6) 0.152(7) -0.016(5) 0.032(5) 0.003(5) C22 0.143(7) 0.140(8) 0.138(7) 0.001(5) 0.025(5) -0.003(5) _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 Ce1 O7 2.443(8) . ? Ce1 O4 2.461(5) . ? Ce1 O3 2.472(5) . ? Ce1 O6 2.473(5) . ? Ce1 O2 2.502(5) . ? Ce1 O8 2.533(7) . ? Ce1 O5 2.534(5) . ? Ce1 O1 2.620(5) . ? Ce1 O6 2.741(5) 7 ? Ce1 C1 2.912(6) . ? Ce1 C16 3.015(7) . ? Ce1 Ce1 4.0909(7) 7 ? O1 C1 1.240(9) . ? O2 C1 1.259(9) . ? O3 C9 1.266(8) . ? O4 C9 1.271(9) 7 ? O5 C16 1.256(8) . ? O6 C16 1.285(8) 7 ? O6 Ce1 2.741(5) 7 ? O7 C17 1.244(5) . ? O8 C20 1.254(5) . ? N1 C8 1.251(10) . ? N1 C12 1.431(8) 8 ? N2 C18 1.446(5) . ? N2 C19 1.450(5) . ? N2 C17 1.453(5) . ? N3 C20 1.449(5) . ? N3 C22 1.452(5) . ? N3 C21 1.456(5) . ? C1 C2 1.511(9) . ? C2 C7 1.369(11) . ? C2 C3 1.381(11) . ? C3 C4 1.395(11) . ? C3 H3 0.9300 . ? C4 C5 1.368(13) . ? C4 H4 0.9300 . ? C5 C6 1.405(12) . ? C5 C8 1.483(10) . ? C6 C7 1.420(10) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H16 1.001(10) . ? C9 O4 1.271(9) 7 ? C9 C10 1.489(10) . ? C10 C15 1.390(10) . ? C10 C11 1.398(9) . ? C11 C12 1.398(9) . ? C11 H11 0.9300 . ? C12 C13 1.407(10) . ? C12 N1 1.431(8) 8_456 ? C13 C14 1.392(8) . ? C13 H13 0.9300 . ? C14 C15 1.406(9) . ? C14 C16 1.494(9) 6_556 ? C15 H15 0.9300 . ? C16 O6 1.285(8) 7 ? C16 C14 1.494(9) 6 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O7 Ce1 O4 135.5(2) . . ? O7 Ce1 O3 75.1(2) . . ? O4 Ce1 O3 133.77(17) . . ? O7 Ce1 O6 83.8(2) . . ? O4 Ce1 O6 72.66(17) . . ? O3 Ce1 O6 80.00(17) . . ? O7 Ce1 O2 89.2(3) . . ? O4 Ce1 O2 80.9(2) . . ? O3 Ce1 O2 142.1(2) . . ? O6 Ce1 O2 133.18(17) . . ? O7 Ce1 O8 74.5(2) . . ? O4 Ce1 O8 139.5(2) . . ? O3 Ce1 O8 70.7(2) . . ? O6 Ce1 O8 147.1(2) . . ? O2 Ce1 O8 71.9(2) . . ? O7 Ce1 O5 147.8(2) . . ? O4 Ce1 O5 74.08(18) . . ? O3 Ce1 O5 92.14(19) . . ? O6 Ce1 O5 123.68(16) . . ? O2 Ce1 O5 83.00(17) . . ? O8 Ce1 O5 73.4(2) . . ? O7 Ce1 O1 69.1(2) . . ? O4 Ce1 O1 71.32(19) . . ? O3 Ce1 O1 142.1(2) . . ? O6 Ce1 O1 84.00(15) . . ? O2 Ce1 O1 50.69(17) . . ? O8 Ce1 O1 110.0(2) . . ? O5 Ce1 O1 125.10(16) . . ? O7 Ce1 O6 140.6(2) . 7 ? O4 Ce1 O6 69.91(16) . 7 ? O3 Ce1 O6 67.94(18) . 7 ? O6 Ce1 O6 76.75(16) . 7 ? O2 Ce1 O6 128.84(19) . 7 ? O8 Ce1 O6 104.8(2) . 7 ? O5 Ce1 O6 49.46(14) . 7 ? O1 Ce1 O6 140.29(18) . 7 ? O7 Ce1 C1 78.5(2) . . ? O4 Ce1 C1 74.26(19) . . ? O3 Ce1 C1 151.2(2) . . ? O6 Ce1 C1 108.48(18) . . ? O2 Ce1 C1 25.49(19) . . ? O8 Ce1 C1 91.3(2) . . ? O5 Ce1 C1 104.43(18) . . ? O1 Ce1 C1 25.20(18) . . ? O6 Ce1 C1 140.24(19) 7 . ? O7 Ce1 C16 153.4(2) . . ? O4 Ce1 C16 69.81(18) . . ? O3 Ce1 C16 79.83(19) . . ? O6 Ce1 C16 100.69(17) . . ? O2 Ce1 C16 105.55(19) . . ? O8 Ce1 C16 89.0(2) . . ? O5 Ce1 C16 24.23(15) . . ? O1 Ce1 C16 137.22(18) . . ? O6 Ce1 C16 25.23(15) 7 . ? C1 Ce1 C16 123.47(19) . . ? O7 Ce1 Ce1 116.87(19) . 7 ? O4 Ce1 Ce1 65.77(11) . 7 ? O3 Ce1 Ce1 69.11(12) . 7 ? O6 Ce1 Ce1 40.71(11) . 7 ? O2 Ce1 Ce1 146.49(17) . 7 ? O8 Ce1 Ce1 132.76(16) . 7 ? O5 Ce1 Ce1 84.24(11) . 7 ? O1 Ce1 Ce1 116.89(13) . 7 ? O6 Ce1 Ce1 36.04(10) 7 7 ? C1 Ce1 Ce1 134.96(16) . 7 ? C16 Ce1 Ce1 60.40(12) . 7 ? C1 O1 Ce1 90.7(4) . . ? C1 O2 Ce1 95.8(4) . . ? C9 O3 Ce1 134.6(5) . . ? C9 O4 Ce1 135.7(5) 7 . ? C16 O5 Ce1 99.9(4) . . ? C16 O6 Ce1 157.5(5) 7 . ? C16 O6 Ce1 89.4(4) 7 7 ? Ce1 O6 Ce1 103.25(16) . 7 ? C17 O7 Ce1 132.9(8) . . ? C20 O8 Ce1 121.2(7) . . ? C8 N1 C12 117.9(7) . 8 ? C18 N2 C19 127.5(14) . . ? C18 N2 C17 110.5(11) . . ? C19 N2 C17 120.6(13) . . ? C20 N3 C22 123.9(11) . . ? C20 N3 C21 107.5(12) . . ? C22 N3 C21 128.5(13) . . ? O1 C1 O2 122.9(6) . . ? O1 C1 C2 120.5(7) . . ? O2 C1 C2 116.6(6) . . ? O1 C1 Ce1 64.1(3) . . ? O2 C1 Ce1 58.8(3) . . ? C2 C1 Ce1 175.2(5) . . ? C7 C2 C3 119.3(7) . . ? C7 C2 C1 119.8(7) . . ? C3 C2 C1 120.9(7) . . ? C2 C3 C4 121.0(8) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.2(8) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.1(7) . . ? C4 C5 C8 119.9(8) . . ? C6 C5 C8 120.0(8) . . ? C5 C6 C7 118.6(8) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C2 C7 C6 120.8(7) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? N1 C8 C5 123.2(8) . . ? N1 C8 H16 140(10) . . ? C5 C8 H16 96(10) . . ? O3 C9 O4 123.9(7) . 7 ? O3 C9 C10 119.1(6) . . ? O4 C9 C10 117.1(6) 7 . ? C15 C10 C11 119.8(6) . . ? C15 C10 C9 120.8(6) . . ? C11 C10 C9 119.4(6) . . ? C10 C11 C12 119.8(6) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 120.4(6) . . ? C11 C12 N1 122.6(6) . 8_456 ? C13 C12 N1 117.1(6) . 8_456 ? C14 C13 C12 119.5(6) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 119.9(6) . . ? C13 C14 C16 120.9(6) . 6_556 ? C15 C14 C16 119.2(5) . 6_556 ? C10 C15 C14 120.5(6) . . ? C10 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? O5 C16 O6 121.3(6) . 7 ? O5 C16 C14 119.8(6) . 6 ? O6 C16 C14 118.9(5) 7 6 ? O5 C16 Ce1 55.9(3) . . ? O6 C16 Ce1 65.4(3) 7 . ? C14 C16 Ce1 175.6(4) 6 . ? O7 C17 N2 116.8(12) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 C20 N3 127.1(11) . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.74 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.934 _refine_diff_density_min -0.992 _refine_diff_density_rms 0.151 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 -0.002 336 53 ' ' 2 0.251 0.750 -0.001 211 35 ' ' 3 0.500 0.001 -0.001 334 53 ' ' 4 0.750 0.250 0.000 209 35 ' ' 5 0.250 0.250 0.500 209 35 ' ' 6 0.750 0.750 0.500 209 35 ' ' data_UCY-5-acetone _database_code_depnum_ccdc_archive 'CCDC 916223' #TrackingRef 'UCY-5-acetone.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 Ce N O8, O' _chemical_formula_sum 'C19 H14 Ce N O9' _chemical_formula_weight 540.43 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.657(2) _cell_length_b 14.2909(5) _cell_length_c 12.8304(9) _cell_angle_alpha 90.00 _cell_angle_beta 124.037(9) _cell_angle_gamma 90.00 _cell_volume 5114.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7140 _cell_measurement_theta_min 2.9154 _cell_measurement_theta_max 29.0304 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2120 _exptl_absorpt_coefficient_mu 1.821 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68411 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19630 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 26.50 _reflns_number_total 5289 _reflns_number_gt 4499 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0833P)^2^+3.6001P] 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 5289 _refine_ls_number_parameters 283 _refine_ls_number_restraints 46 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.148 _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 Ce1 Ce 0.820073(7) 0.288115(16) 0.07760(2) 0.03016(12) Uani 1 1 d . . . O1 O 0.89482(12) 0.3310(3) 0.2903(3) 0.0539(10) Uani 1 1 d . . . O2 O 0.88564(12) 0.1817(3) 0.2410(3) 0.0541(10) Uani 1 1 d . . . O3 O 0.73112(10) 0.3513(2) -0.0050(3) 0.0372(7) Uani 1 1 d . . . O4 O 0.79363(11) 0.4388(2) 0.1227(3) 0.0472(8) Uani 1 1 d . . . O5 O 0.77065(12) 0.3131(3) -0.1485(3) 0.0509(9) Uani 1 1 d . . . O6 O 0.80164(12) 0.2509(3) 0.2330(3) 0.0453(8) Uani 1 1 d . . . O7 O 0.86040(18) 0.4176(4) 0.0364(5) 0.0948(18) Uani 1 1 d . . . O8 O 0.8508(4) 0.1911(7) -0.0305(9) 0.063(2) Uani 0.50 1 d PU . . O8A O 0.8708(5) 0.2234(8) 0.0133(13) 0.084(3) Uani 0.50 1 d PU . . O9 O 0.55005(19) 0.4064(4) 0.8267(7) 0.129(3) Uani 1 1 d . . . C1 C 0.90797(16) 0.2484(4) 0.3187(4) 0.0394(10) Uani 1 1 d . . . C2 C 0.95025(17) 0.2250(3) 0.4472(5) 0.0416(11) Uani 1 1 d . . . C3 C 0.96344(16) 0.1334(4) 0.4843(4) 0.0438(11) Uani 1 1 d . . . H3 H 0.9445 0.0851 0.4306 0.053 Uiso 1 1 calc R . . C4 C 1.00460(16) 0.1124(4) 0.6008(4) 0.0455(12) Uani 1 1 d . . . H4 H 1.0131 0.0504 0.6255 0.055 Uiso 1 1 calc R . . C5 C 1.03309(18) 0.1852(4) 0.6807(5) 0.0551(15) Uani 1 1 d . . . C6 C 1.0188(3) 0.2763(4) 0.6444(7) 0.088(3) Uani 1 1 d . . . H6 H 1.0377 0.3249 0.6976 0.106 Uiso 1 1 calc R . . C7 C 0.9773(2) 0.2967(4) 0.5311(7) 0.079(2) Uani 1 1 d . . . H7 H 0.9671 0.3584 0.5103 0.095 Uiso 1 1 calc R . . C8 C 0.57811(18) 0.6668(4) -0.2003(5) 0.0587(16) Uani 1 1 d D . . C9 C 0.74947(15) 0.4256(3) 0.0591(4) 0.0352(9) Uani 1 1 d . . . C10 C 0.71751(14) 0.4995(3) 0.0566(4) 0.0329(9) Uani 1 1 d . . . C11 C 0.67027(15) 0.5061(3) -0.0446(4) 0.0353(9) Uani 1 1 d . . . H11 H 0.6575 0.4626 -0.1096 0.042 Uiso 1 1 calc R . . C12 C 0.64207(15) 0.5787(3) -0.0480(4) 0.0386(10) Uani 1 1 d . . . C13 C 0.66014(15) 0.6388(3) 0.0541(4) 0.0401(10) Uani 1 1 d . . . H13 H 0.6407 0.6849 0.0543 0.048 Uiso 1 1 calc R . . C14 C 0.70752(15) 0.6297(3) 0.1559(4) 0.0351(9) Uani 1 1 d . . . C15 C 0.73572(14) 0.5617(3) 0.1552(4) 0.0327(9) Uani 1 1 d . . . H15 H 0.7677 0.5571 0.2222 0.039 Uiso 1 1 calc R . . C16 C 0.72746(17) 0.6946(4) 0.2681(4) 0.0387(10) Uani 1 1 d . . . C17 C 0.8800(5) 0.1767(9) -0.0530(14) 0.157(4) Uani 1 1 d DU . . C18 C 0.8786(5) 0.0882(8) -0.1179(13) 0.171(4) Uani 1 1 d DU . . H18A H 0.8876 0.1015 -0.1753 0.257 Uiso 1 1 calc R . . H18B H 0.8467 0.0629 -0.1635 0.257 Uiso 1 1 calc R . . H18C H 0.9005 0.0436 -0.0565 0.257 Uiso 1 1 calc R . . C19 C 0.9276(5) 0.2235(11) -0.0016(18) 0.190(5) Uani 1 1 d DU . . H19A H 0.9413 0.2005 -0.0454 0.286 Uiso 1 1 calc R . . H19B H 0.9489 0.2098 0.0864 0.286 Uiso 1 1 calc R . . H19C H 0.9231 0.2899 -0.0133 0.286 Uiso 1 1 calc R . . N1 N 0.59441(13) 0.5864(3) -0.1594(4) 0.0437(10) Uani 1 1 d . . . H16 H 0.592(2) 0.722(3) -0.154(5) 0.052 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 Ce1 0.02188(17) 0.03280(18) 0.02479(17) 0.00659(8) 0.00630(12) 0.00385(8) O1 0.0410(19) 0.0402(19) 0.0381(19) 0.0054(16) -0.0038(15) -0.0078(16) O2 0.0399(18) 0.0461(19) 0.0312(18) -0.0047(16) -0.0078(15) 0.0181(16) O3 0.0314(15) 0.0309(16) 0.0336(17) 0.0018(12) 0.0085(14) 0.0040(12) O4 0.0242(15) 0.0344(17) 0.057(2) 0.0027(15) 0.0069(15) 0.0036(13) O5 0.0317(18) 0.083(2) 0.0241(17) 0.0141(17) 0.0068(15) -0.0059(17) O6 0.0344(18) 0.058(2) 0.0322(18) 0.0091(17) 0.0116(15) -0.0043(17) O7 0.082(3) 0.113(4) 0.079(3) 0.012(3) 0.039(3) -0.047(3) O8 0.085(4) 0.058(4) 0.041(4) 0.011(3) 0.032(3) 0.018(3) O8A 0.083(5) 0.075(5) 0.083(5) 0.008(3) 0.039(4) 0.016(3) O9 0.065(3) 0.100(4) 0.206(7) -0.044(5) 0.066(4) -0.005(3) C1 0.025(2) 0.048(3) 0.026(2) 0.004(2) 0.0034(19) 0.008(2) C2 0.024(2) 0.047(3) 0.033(3) -0.003(2) 0.003(2) 0.0047(18) C3 0.031(2) 0.045(3) 0.032(2) -0.004(2) 0.004(2) 0.006(2) C4 0.031(2) 0.047(3) 0.033(2) -0.005(2) 0.002(2) 0.010(2) C5 0.037(3) 0.052(3) 0.037(3) -0.011(2) -0.004(2) 0.012(2) C6 0.058(4) 0.055(4) 0.059(4) -0.018(3) -0.024(3) 0.012(3) C7 0.056(4) 0.045(3) 0.057(4) -0.009(3) -0.017(3) 0.016(3) C8 0.039(3) 0.050(3) 0.037(3) -0.015(2) -0.009(2) 0.012(2) C9 0.031(2) 0.032(2) 0.029(2) 0.0082(18) 0.0088(18) 0.0070(17) C10 0.027(2) 0.032(2) 0.028(2) 0.0047(17) 0.0085(17) 0.0047(17) C11 0.027(2) 0.038(2) 0.025(2) -0.0001(17) 0.0054(18) 0.0088(17) C12 0.029(2) 0.045(3) 0.023(2) -0.0032(18) 0.0027(18) 0.0067(19) C13 0.028(2) 0.051(3) 0.027(2) -0.0040(19) 0.0064(18) 0.0103(19) C14 0.029(2) 0.046(3) 0.021(2) -0.0021(18) 0.0086(17) 0.0009(18) C15 0.0244(19) 0.037(2) 0.023(2) 0.0061(17) 0.0051(16) 0.0024(17) C16 0.029(2) 0.054(3) 0.027(2) -0.007(2) 0.012(2) -0.001(2) C17 0.154(5) 0.187(6) 0.171(6) -0.031(4) 0.116(4) 0.009(4) C18 0.186(6) 0.182(6) 0.174(6) -0.028(4) 0.118(5) 0.037(4) C19 0.165(5) 0.222(7) 0.221(7) 0.001(5) 0.131(5) -0.015(4) N1 0.0286(18) 0.049(2) 0.0282(19) -0.0059(17) 0.0006(16) 0.0115(17) _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 Ce1 O5 2.431(3) . ? Ce1 O3 2.452(3) 7_655 ? Ce1 O6 2.455(3) . ? Ce1 O8A 2.456(13) . ? Ce1 O4 2.518(3) . ? Ce1 O7 2.520(4) . ? Ce1 O2 2.529(3) . ? Ce1 O1 2.543(3) . ? Ce1 O8 2.554(10) . ? Ce1 O3 2.711(3) . ? Ce1 C1 2.898(4) . ? Ce1 C9 2.989(4) . ? O1 C1 1.242(6) . ? O2 C1 1.275(6) . ? O3 C9 1.272(5) . ? O3 Ce1 2.452(3) 7_655 ? O4 C9 1.246(5) . ? O5 C16 1.236(6) 6_565 ? O6 C16 1.261(6) 4_645 ? O8 O8A 0.746(14) . ? O8 C17 1.186(14) . ? O8A C17 1.247(16) . ? C1 C2 1.492(6) . ? C2 C3 1.379(6) . ? C2 C7 1.393(8) . ? C3 C4 1.388(6) . ? C3 H3 0.9300 . ? C4 C5 1.397(7) . ? C4 H4 0.9300 . ? C5 C6 1.377(8) . ? C5 C8 1.451(7) 3_546 ? C6 C7 1.371(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N1 1.255(7) . ? C8 C5 1.451(7) 3_454 ? C8 H16 0.93(2) . ? C9 C10 1.494(6) . ? C10 C15 1.379(6) . ? C10 C11 1.383(6) . ? C11 C12 1.391(6) . ? C11 H11 0.9300 . ? C12 C13 1.390(6) . ? C12 N1 1.436(5) . ? C13 C14 1.391(6) . ? C13 H13 0.9300 . ? C14 C15 1.362(6) . ? C14 C16 1.517(6) . ? C15 H15 0.9300 . ? C16 O5 1.236(6) 6_566 ? C16 O6 1.261(6) 4_655 ? C17 C18 1.501(5) . ? C17 C19 1.507(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O5 Ce1 O3 78.45(12) . 7_655 ? O5 Ce1 O6 133.30(11) . . ? O3 Ce1 O6 71.88(12) 7_655 . ? O5 Ce1 O8A 78.1(3) . . ? O3 Ce1 O8A 92.2(3) 7_655 . ? O6 Ce1 O8A 136.9(3) . . ? O5 Ce1 O4 93.14(13) . . ? O3 Ce1 O4 121.26(10) 7_655 . ? O6 Ce1 O4 73.54(13) . . ? O8A Ce1 O4 143.2(3) . . ? O5 Ce1 O7 74.39(15) . . ? O3 Ce1 O7 149.73(15) 7_655 . ? O6 Ce1 O7 137.76(16) . . ? O8A Ce1 O7 69.4(3) . . ? O4 Ce1 O7 73.80(17) . . ? O5 Ce1 O2 140.74(13) . . ? O3 Ce1 O2 85.87(11) 7_655 . ? O6 Ce1 O2 72.31(13) . . ? O8A Ce1 O2 66.7(3) . . ? O4 Ce1 O2 125.47(11) . . ? O7 Ce1 O2 107.03(16) . . ? O5 Ce1 O1 148.29(12) . . ? O3 Ce1 O1 131.77(11) 7_655 . ? O6 Ce1 O1 74.25(12) . . ? O8A Ce1 O1 89.7(3) . . ? O4 Ce1 O1 79.17(12) . . ? O7 Ce1 O1 73.91(15) . . ? O2 Ce1 O1 51.32(11) . . ? O5 Ce1 O8 69.3(2) . . ? O3 Ce1 O8 76.4(3) 7_655 . ? O6 Ce1 O8 133.4(2) . . ? O8A Ce1 O8 17.0(3) . . ? O4 Ce1 O8 153.1(2) . . ? O7 Ce1 O8 81.7(3) . . ? O2 Ce1 O8 72.1(2) . . ? O1 Ce1 O8 104.8(3) . . ? O5 Ce1 O3 67.44(11) . . ? O3 Ce1 O3 74.63(10) 7_655 . ? O6 Ce1 O3 70.37(11) . . ? O8A Ce1 O3 144.9(3) . . ? O4 Ce1 O3 49.45(9) . . ? O7 Ce1 O3 106.25(15) . . ? O2 Ce1 O3 141.67(12) . . ? O1 Ce1 O3 123.50(12) . . ? O8 Ce1 O3 131.5(3) . . ? O5 Ce1 C1 155.57(13) . . ? O3 Ce1 C1 109.06(13) 7_655 . ? O6 Ce1 C1 70.22(13) . . ? O8A Ce1 C1 78.4(3) . . ? O4 Ce1 C1 101.74(13) . . ? O7 Ce1 C1 91.15(16) . . ? O2 Ce1 C1 26.06(13) . . ? O1 Ce1 C1 25.31(14) . . ? O8 Ce1 C1 89.5(2) . . ? O3 Ce1 C1 136.61(12) . . ? O5 Ce1 C9 80.00(13) . . ? O3 Ce1 C9 98.39(11) 7_655 . ? O6 Ce1 C9 69.88(12) . . ? O8A Ce1 C9 153.2(3) . . ? O4 Ce1 C9 24.27(11) . . ? O7 Ce1 C9 89.90(17) . . ? O2 Ce1 C9 138.32(12) . . ? O1 Ce1 C9 101.06(12) . . ? O8 Ce1 C9 149.3(2) . . ? O3 Ce1 C9 25.18(10) . . ? C1 Ce1 C9 120.31(13) . . ? C1 O1 Ce1 93.6(3) . . ? C1 O2 Ce1 93.3(3) . . ? C9 O3 Ce1 155.2(3) . 7_655 ? C9 O3 Ce1 89.7(2) . . ? Ce1 O3 Ce1 105.37(10) 7_655 . ? C9 O4 Ce1 99.5(3) . . ? C16 O5 Ce1 135.0(3) 6_565 . ? C16 O6 Ce1 132.6(3) 4_645 . ? O8A O8 C17 76.7(17) . . ? O8A O8 Ce1 74.1(14) . . ? C17 O8 Ce1 150.3(9) . . ? O8 O8A C17 67.7(15) . . ? O8 O8A Ce1 89.0(15) . . ? C17 O8A Ce1 156.1(11) . . ? O1 C1 O2 121.5(4) . . ? O1 C1 C2 120.0(4) . . ? O2 C1 C2 118.5(4) . . ? O1 C1 Ce1 61.1(2) . . ? O2 C1 Ce1 60.6(2) . . ? C2 C1 Ce1 174.4(4) . . ? C3 C2 C7 119.1(5) . . ? C3 C2 C1 121.1(4) . . ? C7 C2 C1 119.7(5) . . ? C2 C3 C4 120.8(5) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 119.4(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 119.4(5) . . ? C6 C5 C8 119.2(5) . 3_546 ? C4 C5 C8 121.4(5) . 3_546 ? C7 C6 C5 121.0(6) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C2 120.1(5) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? N1 C8 C5 124.1(5) . 3_454 ? N1 C8 H16 124(4) . . ? C5 C8 H16 112(4) 3_454 . ? O4 C9 O3 121.3(4) . . ? O4 C9 C10 119.2(4) . . ? O3 C9 C10 119.5(4) . . ? O4 C9 Ce1 56.2(2) . . ? O3 C9 Ce1 65.1(2) . . ? C10 C9 Ce1 175.4(3) . . ? C15 C10 C11 120.3(4) . . ? C15 C10 C9 119.4(4) . . ? C11 C10 C9 120.3(4) . . ? C10 C11 C12 119.1(4) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C13 C12 C11 120.1(4) . . ? C13 C12 N1 123.1(4) . . ? C11 C12 N1 116.8(4) . . ? C12 C13 C14 119.6(4) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 119.9(4) . . ? C15 C14 C16 120.2(4) . . ? C13 C14 C16 119.9(4) . . ? C14 C15 C10 120.9(4) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? O5 C16 O6 126.6(4) 6_566 4_655 ? O5 C16 C14 116.6(4) 6_566 . ? O6 C16 C14 116.8(4) 4_655 . ? O8 C17 O8A 35.6(7) . . ? O8 C17 C18 120.5(11) . . ? O8A C17 C18 152.3(13) . . ? O8 C17 C19 129.8(11) . . ? O8A C17 C19 94.3(11) . . ? C18 C17 C19 108.2(11) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C8 N1 C12 118.0(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.381 _refine_diff_density_min -1.614 _refine_diff_density_rms 0.134 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.018 0.502 -0.005 1632 293 ' ' data_UCY-5-MeOH _database_code_depnum_ccdc_archive 'CCDC 916224' #TrackingRef 'UCY-5-MeOH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C69 H47 Ce4 N4 O32' _chemical_formula_sum 'C69 H47 Ce4 N4 O32' _chemical_formula_weight 2004.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -1.8482 9.6596 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.667(4) _cell_length_b 14.9105(18) _cell_length_c 12.013(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.274(15) _cell_angle_gamma 90.00 _cell_volume 4929.1(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2139 _cell_measurement_theta_min 3.2093 _cell_measurement_theta_max 66.9856 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1954 _exptl_absorpt_coefficient_mu 14.585 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.32261 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8129 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 67.00 _reflns_number_total 4364 _reflns_number_gt 3807 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.1089P)^2^+17.3344P] 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 4364 _refine_ls_number_parameters 265 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1718 _refine_ls_wR_factor_gt 0.1666 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _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 Ce1 Ce 0.322366(11) 0.22084(2) 0.56942(3) 0.03141(18) Uani 1 1 d . . . O1 O 0.39463(19) 0.1779(4) 0.4951(6) 0.0585(15) Uani 1 1 d . B . O2 O 0.38788(19) 0.3215(3) 0.5332(5) 0.0498(13) Uani 1 1 d . B . O3 O 0.26695(16) 0.3489(3) 0.5309(4) 0.0356(10) Uani 1 1 d . . . O4 O 0.29820(16) 0.0688(3) 0.4818(5) 0.0451(12) Uani 1 1 d . B . O5 O 0.27688(17) 0.1888(4) 0.7081(4) 0.0448(11) Uani 1 1 d . B . O6 O 0.29733(18) 0.2499(4) 0.3606(4) 0.0404(10) Uani 1 1 d . . . O8 O 0.3614(2) 0.3168(5) 0.7478(5) 0.0631(15) Uani 1 1 d . B . N1 N 0.59800(19) 0.4152(4) 0.3569(5) 0.0380(12) Uani 1 1 d . . . C1 C 0.4082(2) 0.2584(5) 0.4951(6) 0.0406(15) Uani 1 1 d . B . C2 C 0.4516(3) 0.2799(5) 0.4526(7) 0.0415(17) Uani 1 1 d . . . C3 C 0.4799(3) 0.2109(5) 0.4299(8) 0.0515(19) Uani 1 1 d . B . H3 H 0.4705 0.1516 0.4343 0.062 Uiso 1 1 calc R . . C4 C 0.5222(3) 0.2305(5) 0.4006(8) 0.051(2) Uani 1 1 d . . . H4 H 0.5416 0.1841 0.3871 0.062 Uiso 1 1 calc R B . C5 C 0.5356(2) 0.3187(5) 0.3913(6) 0.0415(15) Uani 1 1 d . B . C6 C 0.5058(3) 0.3889(5) 0.4093(6) 0.0428(16) Uani 1 1 d . . . H6 H 0.5136 0.4483 0.3990 0.051 Uiso 1 1 calc R B . C7 C 0.4644(2) 0.3681(5) 0.4429(6) 0.0411(15) Uani 1 1 d . B . H7 H 0.4453 0.4139 0.4589 0.049 Uiso 1 1 calc R . . C8 C 0.5826(3) 0.3367(5) 0.3682(6) 0.0428(16) Uani 1 1 d D . . C9 C 0.2527(2) 0.0777(4) 0.4505(6) 0.0382(15) Uani 1 1 d . . . C10 C 0.2218(2) 0.0017(4) 0.3928(6) 0.0363(14) Uani 1 1 d . . . C11 C 0.1742(2) -0.0053(5) 0.3976(6) 0.0386(14) Uani 1 1 d . B . H11 H 0.1613 0.0377 0.4367 0.046 Uiso 1 1 calc R . . C12 C 0.1454(2) -0.0781(4) 0.3426(6) 0.0357(14) Uani 1 1 d . . . C13 C 0.1640(2) -0.1376(4) 0.2772(6) 0.0351(13) Uani 1 1 d . B . H13 H 0.1444 -0.1831 0.2359 0.042 Uiso 1 1 calc R . . C14 C 0.2118(2) -0.1295(5) 0.2729(6) 0.0357(14) Uani 1 1 d . . . C15 C 0.2405(2) -0.0607(4) 0.3314(6) 0.0364(14) Uani 1 1 d . B . H15 H 0.2726 -0.0561 0.3296 0.044 Uiso 1 1 calc R . . C16 C 0.2320(2) 0.1940(5) 0.7019(6) 0.0369(14) Uani 1 1 d . . . C17 C 0.3844(12) 0.116(2) 0.813(3) 0.048(7) Uani 0.25 1 d PU . . H17A H 0.4015 0.0690 0.8626 0.072 Uiso 0.25 1 calc PR A 1 H17B H 0.3566 0.1336 0.8371 0.072 Uiso 0.25 1 calc PR A 1 H17C H 0.4056 0.1664 0.8170 0.072 Uiso 0.25 1 calc PR A 1 O7 O 0.3691(16) 0.084(3) 0.698(4) 0.085(13) Uani 0.25 1 d PU B 1 O7A O 0.3763(3) 0.1168(7) 0.7175(8) 0.055(2) Uani 0.75 1 d PU B 2 C18 C 0.3469(6) 0.3502(11) 0.8404(12) 0.115(5) Uani 1 1 d U . . H18A H 0.3731 0.3835 0.8907 0.173 Uiso 1 1 calc R B . H18B H 0.3382 0.3014 0.8827 0.173 Uiso 1 1 calc R . . H18C H 0.3193 0.3889 0.8121 0.173 Uiso 1 1 calc R . . H16 H 0.595(6) 0.281(6) 0.349(14) 0.138 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 Ce1 0.0223(3) 0.0334(3) 0.0466(3) 0.00231(13) 0.02287(17) -0.00151(11) O1 0.043(3) 0.047(3) 0.105(5) 0.011(3) 0.051(3) 0.000(2) O2 0.044(3) 0.045(3) 0.077(3) -0.015(3) 0.045(3) -0.017(2) O3 0.030(2) 0.031(2) 0.055(3) -0.0025(19) 0.0269(19) -0.0003(17) O4 0.028(2) 0.034(2) 0.083(3) -0.001(2) 0.032(2) 0.0020(18) O5 0.028(2) 0.068(3) 0.051(3) 0.008(2) 0.031(2) -0.003(2) O6 0.038(3) 0.045(2) 0.051(3) 0.000(2) 0.033(2) 0.002(2) O8 0.069(4) 0.067(4) 0.053(3) -0.009(3) 0.017(3) -0.008(3) N1 0.031(3) 0.045(3) 0.049(3) -0.008(2) 0.029(2) -0.006(2) C1 0.023(3) 0.053(4) 0.051(4) 0.003(3) 0.018(3) -0.005(3) C2 0.029(4) 0.056(5) 0.049(4) 0.001(3) 0.026(3) -0.006(3) C3 0.044(4) 0.048(5) 0.073(5) 0.002(4) 0.034(4) -0.004(3) C4 0.040(4) 0.050(5) 0.076(6) 0.000(4) 0.036(4) 0.001(3) C5 0.029(3) 0.053(4) 0.051(4) 0.000(3) 0.027(3) -0.006(3) C6 0.038(4) 0.047(4) 0.054(4) -0.006(3) 0.030(3) -0.009(3) C7 0.032(3) 0.049(4) 0.053(4) -0.008(3) 0.029(3) -0.007(3) C8 0.036(4) 0.052(4) 0.049(4) -0.004(3) 0.026(3) -0.001(3) C9 0.035(3) 0.034(3) 0.056(4) -0.001(3) 0.030(3) -0.008(3) C10 0.029(3) 0.032(3) 0.058(4) -0.001(3) 0.030(3) -0.004(2) C11 0.039(4) 0.033(3) 0.054(4) 0.002(3) 0.031(3) -0.002(3) C12 0.032(3) 0.036(3) 0.049(4) -0.001(3) 0.028(3) -0.003(3) C13 0.031(3) 0.038(3) 0.044(3) -0.001(3) 0.023(3) 0.000(3) C14 0.030(3) 0.041(3) 0.044(3) -0.001(3) 0.023(3) -0.001(3) C15 0.029(3) 0.036(3) 0.055(4) 0.000(3) 0.030(3) 0.000(3) C16 0.035(3) 0.038(4) 0.046(4) 0.002(3) 0.025(3) 0.000(3) C17 0.051(9) 0.051(9) 0.042(9) -0.002(7) 0.012(7) 0.007(7) O7 0.085(14) 0.085(14) 0.085(14) 0.000(5) 0.024(6) 0.000(5) O7A 0.050(4) 0.055(4) 0.057(4) 0.001(3) 0.011(3) 0.012(3) C18 0.130(8) 0.127(8) 0.094(6) -0.008(6) 0.041(6) -0.005(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 Ce1 O5 2.434(4) . ? Ce1 O3 2.443(4) . ? Ce1 O6 2.447(5) . ? Ce1 O4 2.514(5) . ? Ce1 O7A 2.534(9) . ? Ce1 O2 2.535(4) . ? Ce1 O1 2.557(5) . ? Ce1 O8 2.559(6) . ? Ce1 O7 2.68(4) . ? Ce1 O3 2.713(4) 7_556 ? Ce1 C1 2.897(7) . ? Ce1 C9 2.998(7) . ? O1 C1 1.261(10) . ? O2 C1 1.258(10) . ? O3 C9 1.279(8) 7_556 ? O3 Ce1 2.713(4) 7_556 ? O4 C9 1.260(8) . ? O5 C16 1.271(8) . ? O6 C16 1.271(9) 7_556 ? O8 C18 1.385(15) . ? N1 C8 1.271(9) . ? N1 C12 1.419(8) 3 ? C1 C2 1.506(9) . ? C2 C7 1.379(10) . ? C2 C3 1.384(11) . ? C3 C4 1.385(11) . ? C3 H3 0.9300 . ? C4 C5 1.385(11) . ? C4 H4 0.9300 . ? C5 C6 1.407(10) . ? C5 C8 1.475(9) . ? C6 C7 1.391(9) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H16 0.95(2) . ? C9 O3 1.279(8) 7_556 ? C9 C10 1.485(9) . ? C10 C15 1.385(9) . ? C10 C11 1.387(8) . ? C11 C12 1.411(9) . ? C11 H11 0.9300 . ? C12 C13 1.388(9) . ? C12 N1 1.419(8) 3_445 ? C13 C14 1.392(9) . ? C13 H13 0.9300 . ? C14 C15 1.378(9) . ? C14 C16 1.504(9) 6 ? C15 H15 0.9300 . ? C16 O6 1.271(9) 7_556 ? C16 C14 1.504(9) 6_556 ? C17 O7A 1.10(3) . ? C17 O7 1.41(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 O5 Ce1 O3 80.70(17) . . ? O5 Ce1 O6 132.63(16) . . ? O3 Ce1 O6 71.27(16) . . ? O5 Ce1 O4 88.40(18) . . ? O3 Ce1 O4 122.48(15) . . ? O6 Ce1 O4 76.31(18) . . ? O5 Ce1 O7A 74.8(3) . . ? O3 Ce1 O7A 148.0(3) . . ? O6 Ce1 O7A 140.7(3) . . ? O4 Ce1 O7A 77.5(3) . . ? O5 Ce1 O2 142.97(18) . . ? O3 Ce1 O2 88.77(16) . . ? O6 Ce1 O2 74.80(18) . . ? O4 Ce1 O2 126.35(15) . . ? O7A Ce1 O2 98.4(3) . . ? O5 Ce1 O1 146.31(19) . . ? O3 Ce1 O1 132.61(16) . . ? O6 Ce1 O1 73.73(19) . . ? O4 Ce1 O1 77.47(17) . . ? O7A Ce1 O1 72.4(3) . . ? O2 Ce1 O1 51.44(16) . . ? O5 Ce1 O8 74.3(2) . . ? O3 Ce1 O8 80.22(19) . . ? O6 Ce1 O8 133.88(19) . . ? O4 Ce1 O8 149.3(2) . . ? O7A Ce1 O8 73.5(3) . . ? O2 Ce1 O8 68.98(19) . . ? O1 Ce1 O8 103.1(2) . . ? O5 Ce1 O7 74.5(10) . . ? O3 Ce1 O7 153.8(10) . . ? O6 Ce1 O7 133.0(9) . . ? O4 Ce1 O7 65.8(8) . . ? O7A Ce1 O7 11.8(8) . . ? O2 Ce1 O7 105.9(9) . . ? O1 Ce1 O7 71.8(10) . . ? O8 Ce1 O7 84.9(9) . . ? O5 Ce1 O3 66.97(15) . 7_556 ? O3 Ce1 O3 74.48(15) . 7_556 ? O6 Ce1 O3 69.10(15) . 7_556 ? O4 Ce1 O3 49.72(13) . 7_556 ? O7A Ce1 O3 113.1(3) . 7_556 ? O2 Ce1 O3 143.42(16) . 7_556 ? O1 Ce1 O3 120.34(17) . 7_556 ? O8 Ce1 O3 136.30(17) . 7_556 ? O7 Ce1 O3 102.9(9) . 7_556 ? O5 Ce1 C1 155.93(19) . . ? O3 Ce1 C1 110.72(19) . . ? O6 Ce1 C1 71.36(18) . . ? O4 Ce1 C1 101.74(19) . . ? O7A Ce1 C1 86.0(3) . . ? O2 Ce1 C1 25.7(2) . . ? O1 Ce1 C1 25.8(2) . . ? O8 Ce1 C1 86.6(2) . . ? O7 Ce1 C1 89.6(10) . . ? O3 Ce1 C1 135.60(17) 7_556 . ? O5 Ce1 C9 76.89(18) . . ? O3 Ce1 C9 98.91(17) . . ? O6 Ce1 C9 70.91(18) . . ? O4 Ce1 C9 24.46(17) . . ? O7A Ce1 C9 95.3(3) . . ? O2 Ce1 C9 140.06(17) . . ? O1 Ce1 C9 98.76(18) . . ? O8 Ce1 C9 150.89(19) . . ? O7 Ce1 C9 83.8(9) . . ? O3 Ce1 C9 25.26(15) 7_556 . ? C1 Ce1 C9 120.1(2) . . ? C1 O1 Ce1 92.3(4) . . ? C1 O2 Ce1 93.4(4) . . ? C9 O3 Ce1 158.5(4) 7_556 . ? C9 O3 Ce1 90.0(4) 7_556 7_556 ? Ce1 O3 Ce1 105.52(15) . 7_556 ? C9 O4 Ce1 99.8(4) . . ? C16 O5 Ce1 132.5(4) . . ? C16 O6 Ce1 132.6(4) 7_556 . ? C18 O8 Ce1 135.6(8) . . ? C8 N1 C12 116.7(6) . 3 ? O2 C1 O1 122.6(6) . . ? O2 C1 C2 118.3(7) . . ? O1 C1 C2 119.1(7) . . ? O2 C1 Ce1 60.9(3) . . ? O1 C1 Ce1 61.9(4) . . ? C2 C1 Ce1 177.8(5) . . ? C7 C2 C3 120.5(6) . . ? C7 C2 C1 119.8(6) . . ? C3 C2 C1 119.6(7) . . ? C2 C3 C4 119.8(7) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.3(7) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.0(6) . . ? C4 C5 C8 118.5(7) . . ? C6 C5 C8 121.4(7) . . ? C7 C6 C5 118.9(7) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C2 C7 C6 120.5(7) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? N1 C8 C5 123.3(7) . . ? N1 C8 H16 128(10) . . ? C5 C8 H16 108(10) . . ? O4 C9 O3 120.5(6) . 7_556 ? O4 C9 C10 119.4(6) . . ? O3 C9 C10 120.1(6) 7_556 . ? O4 C9 Ce1 55.7(3) . . ? O3 C9 Ce1 64.8(3) 7_556 . ? C10 C9 Ce1 175.1(5) . . ? C15 C10 C11 120.3(6) . . ? C15 C10 C9 119.5(5) . . ? C11 C10 C9 120.2(6) . . ? C10 C11 C12 119.5(6) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 119.3(6) . . ? C13 C12 N1 123.9(6) . 3_445 ? C11 C12 N1 116.8(6) . 3_445 ? C12 C13 C14 120.4(6) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 119.9(6) . . ? C15 C14 C16 119.8(6) . 6 ? C13 C14 C16 120.3(6) . 6 ? C14 C15 C10 120.4(6) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? O6 C16 O5 124.4(6) 7_556 . ? O6 C16 C14 117.4(6) 7_556 6_556 ? O5 C16 C14 118.1(6) . 6_556 ? O7A C17 O7 21.4(19) . . ? O7A C17 H17A 125.4 . . ? O7 C17 H17A 109.5 . . ? O7A C17 H17B 111.2 . . ? O7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O7A C17 H17C 89.5 . . ? O7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C17 O7 Ce1 106(3) . . ? C17 O7A Ce1 130.3(18) . . ? O8 C18 H18A 109.5 . . ? O8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.730 _refine_diff_density_min -3.446 _refine_diff_density_rms 0.149 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.018 0.468 -0.019 1907 495 ' ' data_UCY-6 _database_code_depnum_ccdc_archive 'CCDC 916225' #TrackingRef 'UCY-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 N3 O8 Pr' _chemical_formula_sum 'C22 H20 N3 O8 Pr' _chemical_formula_weight 595.32 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.877(2) _cell_length_b 14.3145(9) _cell_length_c 13.6347(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.644(9) _cell_angle_gamma 90.00 _cell_volume 5556.4(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4781 _cell_measurement_theta_min 2.9997 _cell_measurement_theta_max 28.5395 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2368 _exptl_absorpt_coefficient_mu 1.797 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.28479 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10719 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5458 _reflns_number_gt 3976 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.1399P)^2^+0.1242P] 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 5458 _refine_ls_number_parameters 310 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.2280 _refine_ls_wR_factor_gt 0.2086 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.173 _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 Pr1 Pr 0.181727(13) 0.21268(3) 0.95680(3) 0.0345(2) Uani 1 1 d . . . O1 O 0.1189(2) 0.3276(5) 0.9941(6) 0.067(2) Uani 1 1 d . . . O2 O 0.1067(2) 0.1804(5) 1.0177(7) 0.071(2) Uani 1 1 d . . . O3 O 0.26768(19) 0.1507(4) 1.0386(4) 0.0447(14) Uani 1 1 d . . . O4 O 0.2056(2) 0.0662(4) 1.0537(5) 0.0534(16) Uani 1 1 d . . . O5 O 0.2285(2) 0.1684(6) 0.8310(5) 0.0635(19) Uani 1 1 d . . . O6 O 0.2010(2) 0.2620(5) 1.1299(5) 0.0546(17) Uani 1 1 d . . . O7 O 0.1418(5) 0.2841(7) 0.8028(10) 0.118(3) Uani 1 1 d DU . . O8 O 0.1401(4) 0.0823(7) 0.8561(9) 0.113(3) Uani 1 1 d DU . . N1 N -0.0985(3) 0.4171(6) 1.1493(6) 0.054(2) Uani 1 1 d . . . N2 N 0.1159(7) 0.3811(14) 0.6646(14) 0.177(5) Uani 1 1 d DU . . N3 N 0.1157(7) 0.0151(12) 0.6861(11) 0.167(4) Uani 1 1 d DU . . C1 C 0.0950(3) 0.2624(8) 1.0214(8) 0.052(2) Uani 1 1 d . . . C2 C 0.0501(3) 0.2838(7) 1.0571(8) 0.055(3) Uani 1 1 d . . . C3 C 0.0211(5) 0.2125(7) 1.0808(13) 0.090(5) Uani 1 1 d . . . H3 H 0.0313 0.1510 1.0795 0.109 Uiso 1 1 calc R . . C4 C -0.0220(5) 0.2300(8) 1.1059(13) 0.098(5) Uani 1 1 d . . . H4 H -0.0423 0.1812 1.1134 0.118 Uiso 1 1 calc R . . C5 C -0.0349(4) 0.3217(8) 1.1198(8) 0.063(3) Uani 1 1 d . . . C6 C -0.0071(4) 0.3935(8) 1.0967(9) 0.075(3) Uani 1 1 d . . . H6 H -0.0167 0.4552 1.1011 0.090 Uiso 1 1 calc R . . C7 C 0.0361(3) 0.3733(8) 1.0663(9) 0.068(3) Uani 1 1 d . . . H7 H 0.0553 0.4220 1.0524 0.082 Uiso 1 1 calc R . . C8 C -0.0817(4) 0.3388(8) 1.1446(9) 0.066(3) Uani 1 1 d D . . H16 H -0.100(4) 0.286(5) 1.118(8) 0.079 Uiso 1 1 d D . . C9 C 0.2490(3) 0.0787(5) 1.0700(6) 0.0387(18) Uani 1 1 d . . . C10 C 0.2801(3) 0.0050(6) 1.1280(6) 0.0417(19) Uani 1 1 d . . . C11 C 0.2612(3) -0.0542(6) 1.1932(6) 0.0387(18) Uani 1 1 d . . . H11 H 0.2298 -0.0485 1.2003 0.046 Uiso 1 1 calc R . . C12 C 0.2895(3) -0.1215(6) 1.2473(6) 0.0407(19) Uani 1 1 d . . . C13 C 0.3366(3) -0.1298(6) 1.2369(6) 0.0396(18) Uani 1 1 d . . . H13 H 0.3561 -0.1722 1.2758 0.048 Uiso 1 1 calc R . . C14 C 0.3542(3) -0.0737(6) 1.1672(7) 0.049(2) Uani 1 1 d . . . C15 C 0.3271(3) -0.0031(6) 1.1190(7) 0.045(2) Uani 1 1 d . . . H15 H 0.3404 0.0394 1.0802 0.055 Uiso 1 1 calc R . . C16 C 0.2711(3) 0.1786(7) 0.8215(6) 0.047(2) Uani 1 1 d . . . C17 C 0.1519(8) 0.3304(17) 0.7319(15) 0.175(5) Uani 1 1 d DU . . C18 C 0.0736(8) 0.3886(18) 0.7087(18) 0.193(6) Uani 1 1 d DU . . H18A H 0.0687 0.3313 0.7421 0.289 Uiso 1 1 calc R . . H18B H 0.0471 0.4004 0.6574 0.289 Uiso 1 1 calc R . . H18C H 0.0770 0.4391 0.7557 0.289 Uiso 1 1 calc R . . C19 C 0.1488(8) 0.4199(17) 0.6060(17) 0.181(6) Uani 1 1 d DU . . H19A H 0.1711 0.3729 0.5953 0.271 Uiso 1 1 calc R . . H19B H 0.1650 0.4718 0.6409 0.271 Uiso 1 1 calc R . . H19C H 0.1321 0.4408 0.5431 0.271 Uiso 1 1 calc R . . C20 C 0.1330(9) 0.0830(15) 0.7627(10) 0.170(4) Uani 1 1 d DU . . C21 C 0.1010(9) 0.0245(17) 0.5791(12) 0.178(5) Uani 1 1 d DU . . H21A H 0.0916 -0.0354 0.5509 0.267 Uiso 1 1 calc R . . H21B H 0.1266 0.0480 0.5498 0.267 Uiso 1 1 calc R . . H21C H 0.0750 0.0671 0.5660 0.267 Uiso 1 1 calc R . . C22 C 0.1279(9) -0.0653(15) 0.7511(17) 0.192(5) Uani 1 1 d DU . . H22A H 0.1394 -0.0440 0.8175 0.287 Uiso 1 1 calc R . . H22B H 0.1518 -0.1013 0.7274 0.287 Uiso 1 1 calc R . . H22C H 0.1005 -0.1034 0.7513 0.287 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pr1 0.0228(3) 0.0404(3) 0.0439(3) -0.00227(18) 0.0166(2) 0.00162(16) O1 0.045(4) 0.068(4) 0.099(5) 0.014(4) 0.047(4) 0.013(3) O2 0.046(4) 0.053(4) 0.127(7) 0.001(4) 0.052(4) -0.003(3) O3 0.034(3) 0.046(3) 0.059(4) 0.007(3) 0.023(3) 0.007(2) O4 0.036(3) 0.042(3) 0.089(5) 0.011(3) 0.029(3) 0.006(3) O5 0.034(3) 0.105(5) 0.056(4) -0.030(4) 0.021(3) -0.003(4) O6 0.048(4) 0.072(4) 0.051(4) -0.019(3) 0.028(3) -0.013(3) O7 0.112(5) 0.122(5) 0.119(5) -0.030(3) 0.013(4) 0.007(4) O8 0.085(4) 0.117(5) 0.141(4) 0.008(4) 0.033(4) -0.011(4) N1 0.043(4) 0.066(5) 0.061(5) 0.014(4) 0.030(4) 0.017(4) N2 0.186(6) 0.174(6) 0.172(6) 0.018(4) 0.026(4) 0.003(4) N3 0.169(7) 0.171(5) 0.159(4) -0.010(3) 0.020(5) 0.001(5) C1 0.032(5) 0.068(6) 0.059(6) -0.001(5) 0.020(4) 0.002(5) C2 0.034(5) 0.074(7) 0.063(6) -0.004(5) 0.023(5) 0.004(4) C3 0.072(9) 0.056(7) 0.164(15) -0.001(7) 0.078(10) -0.001(5) C4 0.083(10) 0.060(7) 0.171(16) 0.015(8) 0.077(11) 0.005(6) C5 0.065(7) 0.064(6) 0.069(7) 0.020(5) 0.033(5) 0.011(5) C6 0.070(7) 0.073(7) 0.090(8) 0.026(6) 0.041(6) 0.019(6) C7 0.044(5) 0.067(7) 0.104(8) 0.024(6) 0.041(6) 0.008(5) C8 0.057(6) 0.074(8) 0.074(7) 0.019(6) 0.033(5) 0.006(6) C9 0.039(4) 0.031(4) 0.052(5) 0.001(4) 0.024(4) 0.002(3) C10 0.030(4) 0.042(5) 0.057(5) 0.005(4) 0.020(4) 0.003(3) C11 0.032(4) 0.047(5) 0.041(4) -0.009(4) 0.019(3) 0.000(4) C12 0.039(4) 0.053(5) 0.034(4) 0.001(4) 0.018(3) 0.006(4) C13 0.036(4) 0.046(5) 0.042(4) 0.009(4) 0.023(3) 0.007(4) C14 0.037(4) 0.060(6) 0.059(5) 0.015(5) 0.029(4) 0.011(4) C15 0.035(4) 0.042(5) 0.066(5) 0.015(4) 0.029(4) 0.008(4) C16 0.044(5) 0.065(6) 0.037(4) -0.014(4) 0.021(4) -0.011(4) C17 0.180(6) 0.175(7) 0.169(6) 0.012(4) 0.027(4) -0.005(4) C18 0.184(6) 0.196(8) 0.198(8) 0.001(5) 0.033(5) -0.001(5) C19 0.191(7) 0.179(7) 0.171(6) 0.012(5) 0.027(5) -0.006(5) C20 0.174(7) 0.183(6) 0.154(4) -0.009(4) 0.028(5) -0.003(5) C21 0.185(7) 0.183(7) 0.164(5) -0.010(4) 0.022(5) -0.002(5) C22 0.198(8) 0.184(5) 0.192(6) 0.014(4) 0.031(5) -0.004(5) _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 Pr1 O3 2.436(6) 7_557 ? Pr1 O6 2.437(6) . ? Pr1 O5 2.439(6) . ? Pr1 O7 2.444(14) . ? Pr1 O2 2.489(6) . ? Pr1 O8 2.503(11) . ? Pr1 O4 2.512(6) . ? Pr1 O1 2.563(6) . ? Pr1 O3 2.695(5) . ? Pr1 C1 2.879(9) . ? Pr1 C9 2.971(8) . ? Pr1 Pr1 4.0645(8) 7_557 ? O1 C1 1.253(12) . ? O2 C1 1.226(13) . ? O3 C9 1.271(9) . ? O3 Pr1 2.436(6) 7_557 ? O4 C9 1.248(9) . ? O5 C16 1.265(10) . ? O6 C16 1.278(11) 7_557 ? O7 C17 1.246(5) . ? O8 C20 1.255(5) . ? N1 C8 1.227(13) . ? N1 C14 1.433(10) 3_455 ? N2 C19 1.450(5) . ? N2 C18 1.454(5) . ? N2 C17 1.458(5) . ? N3 C20 1.454(5) . ? N3 C21 1.456(5) . ? N3 C22 1.459(5) . ? C1 C2 1.493(12) . ? C2 C7 1.355(13) . ? C2 C3 1.391(14) . ? C3 C4 1.368(16) . ? C3 H3 0.9300 . ? C4 C5 1.385(16) . ? C4 H4 0.9300 . ? C5 C6 1.373(15) . ? C5 C8 1.468(14) . ? C6 C7 1.409(13) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H16 0.96(2) . ? C9 C10 1.518(11) . ? C10 C15 1.389(10) . ? C10 C11 1.403(11) . ? C11 C12 1.392(11) . ? C11 H11 0.9300 . ? C12 C13 1.396(10) . ? C12 C16 1.468(11) 6_556 ? C13 C14 1.403(11) . ? C13 H13 0.9300 . ? C14 C15 1.376(11) . ? C14 N1 1.433(10) 3_545 ? C15 H15 0.9300 . ? C16 O6 1.278(11) 7_557 ? C16 C12 1.468(11) 6 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O3 Pr1 O6 72.8(2) 7_557 . ? O3 Pr1 O5 80.0(2) 7_557 . ? O6 Pr1 O5 133.8(2) . . ? O3 Pr1 O7 83.1(3) 7_557 . ? O6 Pr1 O7 135.2(3) . . ? O5 Pr1 O7 75.0(3) . . ? O3 Pr1 O2 133.8(2) 7_557 . ? O6 Pr1 O2 78.6(3) . . ? O5 Pr1 O2 143.3(3) . . ? O7 Pr1 O2 93.0(4) . . ? O3 Pr1 O8 147.6(3) 7_557 . ? O6 Pr1 O8 139.3(3) . . ? O5 Pr1 O8 72.1(3) . . ? O7 Pr1 O8 74.1(3) . . ? O2 Pr1 O8 71.3(3) . . ? O3 Pr1 O4 123.1(2) 7_557 . ? O6 Pr1 O4 74.6(2) . . ? O5 Pr1 O4 91.0(2) . . ? O7 Pr1 O4 148.1(3) . . ? O2 Pr1 O4 81.2(2) . . ? O8 Pr1 O4 74.3(3) . . ? O3 Pr1 O1 85.5(2) 7_557 . ? O6 Pr1 O1 71.1(3) . . ? O5 Pr1 O1 143.2(3) . . ? O7 Pr1 O1 69.8(3) . . ? O2 Pr1 O1 50.8(2) . . ? O8 Pr1 O1 107.2(3) . . ? O4 Pr1 O1 124.9(2) . . ? O3 Pr1 O3 75.3(2) 7_557 . ? O6 Pr1 O3 69.5(2) . . ? O5 Pr1 O3 68.0(2) . . ? O7 Pr1 O3 139.7(3) . . ? O2 Pr1 O3 126.4(2) . . ? O8 Pr1 O3 107.8(3) . . ? O4 Pr1 O3 49.86(18) . . ? O1 Pr1 O3 139.7(2) . . ? O3 Pr1 C1 110.0(3) 7_557 . ? O6 Pr1 C1 72.6(3) . . ? O5 Pr1 C1 153.2(3) . . ? O7 Pr1 C1 81.4(4) . . ? O2 Pr1 C1 25.1(3) . . ? O8 Pr1 C1 89.4(3) . . ? O4 Pr1 C1 102.8(3) . . ? O1 Pr1 C1 25.8(3) . . ? O3 Pr1 C1 138.0(2) . . ? O3 Pr1 C9 99.7(2) 7_557 . ? O6 Pr1 C9 70.1(2) . . ? O5 Pr1 C9 78.8(2) . . ? O7 Pr1 C9 152.8(3) . . ? O2 Pr1 C9 103.7(2) . . ? O8 Pr1 C9 90.9(3) . . ? O4 Pr1 C9 24.53(19) . . ? O1 Pr1 C9 137.2(2) . . ? O3 Pr1 C9 25.33(18) . . ? C1 Pr1 C9 121.8(3) . . ? O3 Pr1 Pr1 39.90(13) 7_557 7_557 ? O6 Pr1 Pr1 65.78(15) . 7_557 ? O5 Pr1 Pr1 69.33(15) . 7_557 ? O7 Pr1 Pr1 115.7(3) . 7_557 ? O2 Pr1 Pr1 143.9(2) . 7_557 ? O8 Pr1 Pr1 135.1(2) . 7_557 ? O4 Pr1 Pr1 84.25(14) . 7_557 ? O1 Pr1 Pr1 117.29(18) . 7_557 ? O3 Pr1 Pr1 35.43(12) . 7_557 ? C1 Pr1 Pr1 134.2(2) . 7_557 ? C9 Pr1 Pr1 60.08(15) . 7_557 ? C1 O1 Pr1 91.4(6) . . ? C1 O2 Pr1 95.6(5) . . ? C9 O3 Pr1 158.4(6) . 7_557 ? C9 O3 Pr1 89.6(5) . . ? Pr1 O3 Pr1 104.7(2) 7_557 . ? C9 O4 Pr1 98.8(5) . . ? C16 O5 Pr1 134.8(6) . . ? C16 O6 Pr1 135.8(6) 7_557 . ? C17 O7 Pr1 138.8(14) . . ? C20 O8 Pr1 122.1(12) . . ? C8 N1 C14 119.3(8) . 3_455 ? C19 N2 C18 151(2) . . ? C19 N2 C17 94.3(15) . . ? C18 N2 C17 109.6(19) . . ? C20 N3 C21 131.7(17) . . ? C20 N3 C22 94.1(16) . . ? C21 N3 C22 133.0(19) . . ? O2 C1 O1 122.1(8) . . ? O2 C1 C2 118.1(9) . . ? O1 C1 C2 119.8(9) . . ? O2 C1 Pr1 59.4(4) . . ? O1 C1 Pr1 62.8(5) . . ? C2 C1 Pr1 177.3(8) . . ? C7 C2 C3 118.2(9) . . ? C7 C2 C1 120.8(9) . . ? C3 C2 C1 121.0(9) . . ? C4 C3 C2 122.1(10) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 119.0(11) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 119.8(10) . . ? C6 C5 C8 121.6(10) . . ? C4 C5 C8 118.0(11) . . ? C5 C6 C7 119.6(10) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C2 C7 C6 120.9(10) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? N1 C8 C5 123.5(10) . . ? N1 C8 H16 122(7) . . ? C5 C8 H16 105(8) . . ? O4 C9 O3 121.8(7) . . ? O4 C9 C10 118.8(7) . . ? O3 C9 C10 119.4(7) . . ? O4 C9 Pr1 56.7(4) . . ? O3 C9 Pr1 65.1(4) . . ? C10 C9 Pr1 175.5(5) . . ? C15 C10 C11 119.6(7) . . ? C15 C10 C9 121.0(7) . . ? C11 C10 C9 119.4(7) . . ? C12 C11 C10 119.9(7) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.1(7) . . ? C11 C12 C16 120.2(7) . 6_556 ? C13 C12 C16 119.6(7) . 6_556 ? C12 C13 C14 119.3(7) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 120.2(7) . . ? C15 C14 N1 117.9(7) . 3_545 ? C13 C14 N1 121.8(8) . 3_545 ? C14 C15 C10 120.4(7) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? O5 C16 O6 124.2(8) . 7_557 ? O5 C16 C12 118.5(8) . 6 ? O6 C16 C12 117.3(7) 7_557 6 ? O7 C17 N2 121.3(19) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 C20 N3 134.5(19) . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.899 _refine_diff_density_min -1.262 _refine_diff_density_rms 0.197 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.250 0.750 0.000 196 34 ' ' 2 0.750 0.250 0.000 196 34 ' ' 3 0.500 0.398 0.250 149 26 ' ' 4 1.000 0.898 0.250 149 26 ' ' 5 0.250 0.250 0.500 196 34 ' ' 6 0.750 0.750 0.500 196 34 ' ' 7 0.500 0.605 0.750 146 25 ' ' 8 1.000 0.105 0.750 146 25 ' ' data_UCY-7 _database_code_depnum_ccdc_archive 'CCDC 916226' #TrackingRef 'UCY-7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H34 N5 O16 Sm2' _chemical_formula_sum 'C41 H34 N5 O16 Sm2' _chemical_formula_weight 1153.45 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 Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.8085(10) _cell_length_b 14.3140(7) _cell_length_c 13.5515(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.776(4) _cell_angle_gamma 90.00 _cell_volume 5507.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5249 _cell_measurement_theta_min 3.0068 _cell_measurement_theta_max 28.5141 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2268 _exptl_absorpt_coefficient_mu 2.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75770 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13354 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 26.50 _reflns_number_total 5689 _reflns_number_gt 4379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0684P)^2^+30.2667P] 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 5689 _refine_ls_number_parameters 320 _refine_ls_number_restraints 115 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.132 _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 Sm1 Sm 0.817457(9) 0.71257(2) 0.04206(2) 0.03249(13) Uani 1 1 d . . . O1 O 0.87952(16) 0.8282(4) 0.0063(4) 0.0583(14) Uani 1 1 d . . . O2 O 0.89127(18) 0.6793(4) -0.0181(5) 0.0661(16) Uani 1 1 d . . . O3 O 0.76857(14) 0.8473(3) 0.0406(3) 0.0415(10) Uani 1 1 d . . . O4 O 0.79396(15) 0.5687(3) -0.0532(4) 0.0475(11) Uani 1 1 d . . . O5 O 0.79896(16) 0.7620(4) -0.1290(3) 0.0463(11) Uani 1 1 d . . . O6 O 0.77129(16) 0.6671(4) 0.1665(4) 0.0563(13) Uani 1 1 d . . . O7 O 0.8607(5) 0.5963(8) 0.1478(9) 0.054(3) Uani 0.50 1 d PDU . . O7A O 0.8547(6) 0.5614(10) 0.1361(12) 0.071(3) Uani 0.50 1 d PU . . O8 O 0.8573(3) 0.7812(6) 0.1959(6) 0.104(2) Uani 1 1 d DU . . N1 N 1.09847(19) 0.9187(5) -0.1487(5) 0.0522(15) Uani 1 1 d . . . N2 N 0.8843(5) 0.5146(9) 0.3106(9) 0.076(3) Uani 0.50 1 d PDU . . N3 N 0.8799(5) 0.8769(10) 0.3292(11) 0.166(4) Uani 1 1 d DU . . C1 C 0.9035(2) 0.7623(6) -0.0210(5) 0.0487(17) Uani 1 1 d . . . C2 C 0.9488(3) 0.7844(5) -0.0575(6) 0.0534(19) Uani 1 1 d . . . C3 C 0.9635(3) 0.8739(6) -0.0649(7) 0.063(2) Uani 1 1 d . . . H3 H 0.9447 0.9227 -0.0494 0.075 Uiso 1 1 calc R . . C4 C 1.0060(3) 0.8940(6) -0.0951(7) 0.064(2) Uani 1 1 d . . . H4 H 1.0159 0.9555 -0.0986 0.077 Uiso 1 1 calc R . . C5 C 1.0337(3) 0.8207(6) -0.1202(7) 0.061(2) Uani 1 1 d . . . C6 C 1.0198(4) 0.7323(7) -0.1137(10) 0.098(4) Uani 1 1 d . . . H6 H 1.0387 0.6837 -0.1293 0.117 Uiso 1 1 calc R . . C7 C 0.9767(3) 0.7131(6) -0.0836(11) 0.097(4) Uani 1 1 d . . . H7 H 0.9668 0.6515 -0.0810 0.116 Uiso 1 1 calc R . . C8 C 1.0810(3) 0.8391(7) -0.1454(7) 0.068(2) Uani 1 1 d D . . H16 H 1.094(3) 0.779(3) -0.156(7) 0.081 Uiso 1 1 d D . . C9 C 0.7503(2) 0.5804(4) -0.0713(5) 0.0376(14) Uani 1 1 d . . . C10 C 0.7196(2) 0.5066(4) -0.1290(5) 0.0386(14) Uani 1 1 d . . . C11 C 0.7386(2) 0.4471(4) -0.1933(5) 0.0360(13) Uani 1 1 d . . . H11 H 0.7702 0.4518 -0.1992 0.043 Uiso 1 1 calc R . . C12 C 0.7102(2) 0.3810(5) -0.2480(5) 0.0403(15) Uani 1 1 d . . . C13 C 0.6635(2) 0.3706(5) -0.2360(5) 0.0408(15) Uani 1 1 d . . . H13 H 0.6445 0.3256 -0.2725 0.049 Uiso 1 1 calc R . . C14 C 0.6451(2) 0.4289(5) -0.1678(5) 0.0448(16) Uani 1 1 d . . . C15 C 0.6723(2) 0.4979(5) -0.1184(5) 0.0430(15) Uani 1 1 d . . . H15 H 0.6594 0.5393 -0.0776 0.052 Uiso 1 1 calc R . . C16 C 0.7714(2) 0.8204(5) -0.1763(5) 0.0417(15) Uani 1 1 d . . . C17 C 0.8674(7) 0.5886(12) 0.2412(10) 0.083(3) Uani 0.50 1 d PDU . . C18 C 0.8734(9) 0.4341(13) 0.2455(16) 0.107(5) Uani 0.50 1 d PDU . . H18A H 0.8830 0.3781 0.2824 0.161 Uiso 0.50 1 calc PR . . H18B H 0.8899 0.4390 0.1899 0.161 Uiso 0.50 1 calc PR . . H18C H 0.8402 0.4319 0.2213 0.161 Uiso 0.50 1 calc PR . . C19 C 0.9026(8) 0.5281(15) 0.4160(10) 0.089(4) Uani 0.50 1 d PDU . . H19A H 0.9122 0.4690 0.4462 0.133 Uiso 0.50 1 calc PR . . H19B H 0.8785 0.5545 0.4483 0.133 Uiso 0.50 1 calc PR . . H19C H 0.9291 0.5696 0.4233 0.133 Uiso 0.50 1 calc PR . . C20 C 0.8437(5) 0.8210(12) 0.2676(11) 0.155(3) Uani 1 1 d DU . . C21 C 0.8558(7) 0.9261(13) 0.3985(13) 0.180(5) Uani 1 1 d DU . . H21A H 0.8250 0.8998 0.3963 0.270 Uiso 1 1 calc R . . H21B H 0.8529 0.9909 0.3804 0.270 Uiso 1 1 calc R . . H21C H 0.8734 0.9202 0.4651 0.270 Uiso 1 1 calc R . . C22 C 0.9273(6) 0.8892(14) 0.3082(15) 0.186(5) Uani 1 1 d DU . . H22A H 0.9332 0.8437 0.2599 0.279 Uiso 1 1 calc R . . H22B H 0.9496 0.8813 0.3689 0.279 Uiso 1 1 calc R . . H22C H 0.9304 0.9509 0.2821 0.279 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sm1 0.02026(18) 0.0389(2) 0.0420(2) 0.00157(14) 0.01569(13) -0.00146(12) O1 0.035(3) 0.065(3) 0.084(4) -0.025(3) 0.036(3) -0.015(2) O2 0.045(3) 0.052(3) 0.113(5) 0.008(3) 0.048(3) 0.005(2) O3 0.033(2) 0.038(2) 0.059(3) -0.007(2) 0.025(2) -0.0038(18) O4 0.031(2) 0.038(2) 0.077(3) -0.011(2) 0.021(2) -0.0049(19) O5 0.035(2) 0.065(3) 0.044(2) 0.011(2) 0.021(2) 0.008(2) O6 0.031(2) 0.085(4) 0.058(3) 0.024(3) 0.023(2) 0.007(2) O7 0.038(4) 0.055(5) 0.067(4) 0.003(4) 0.004(4) 0.013(4) O7A 0.061(5) 0.070(5) 0.080(4) -0.008(4) 0.008(4) 0.007(4) O8 0.104(5) 0.126(6) 0.075(4) 0.024(3) -0.004(4) -0.024(4) N1 0.034(3) 0.068(4) 0.061(4) -0.015(3) 0.028(3) -0.018(3) N2 0.074(5) 0.076(5) 0.079(4) 0.008(3) 0.013(4) 0.002(4) N3 0.173(5) 0.163(5) 0.160(5) -0.018(4) 0.020(4) -0.008(4) C1 0.027(3) 0.075(5) 0.049(4) -0.002(4) 0.018(3) -0.002(3) C2 0.033(4) 0.068(5) 0.065(5) -0.002(4) 0.025(3) -0.009(3) C3 0.042(4) 0.070(5) 0.083(6) -0.018(5) 0.028(4) -0.005(4) C4 0.049(4) 0.069(5) 0.082(6) -0.017(5) 0.033(4) -0.012(4) C5 0.057(5) 0.057(4) 0.078(5) -0.015(4) 0.037(4) -0.015(4) C6 0.068(6) 0.070(6) 0.174(12) -0.032(7) 0.076(7) -0.012(5) C7 0.058(6) 0.065(6) 0.189(13) -0.017(6) 0.080(7) -0.008(4) C8 0.053(5) 0.076(6) 0.084(6) -0.020(5) 0.041(4) -0.010(4) C9 0.035(3) 0.038(3) 0.046(3) -0.005(3) 0.022(3) -0.006(3) C10 0.031(3) 0.039(3) 0.052(4) -0.003(3) 0.024(3) -0.005(3) C11 0.025(3) 0.044(3) 0.043(3) 0.001(3) 0.019(3) -0.002(2) C12 0.035(3) 0.047(4) 0.045(3) 0.002(3) 0.023(3) -0.004(3) C13 0.036(3) 0.049(4) 0.043(3) -0.009(3) 0.022(3) -0.009(3) C14 0.028(3) 0.058(4) 0.055(4) -0.012(3) 0.024(3) -0.011(3) C15 0.035(3) 0.045(4) 0.057(4) -0.011(3) 0.030(3) -0.005(3) C16 0.035(3) 0.057(4) 0.038(3) 0.008(3) 0.021(3) 0.003(3) C17 0.083(6) 0.092(5) 0.074(3) 0.007(4) 0.015(4) 0.002(5) C18 0.113(7) 0.101(5) 0.108(6) -0.015(4) 0.022(5) 0.000(5) C19 0.092(6) 0.088(6) 0.085(4) 0.006(4) 0.014(4) -0.001(5) C20 0.156(4) 0.156(4) 0.152(4) -0.0006(19) 0.025(2) 0.000(2) C21 0.191(6) 0.179(6) 0.170(6) -0.012(4) 0.028(4) 0.003(5) C22 0.176(5) 0.189(7) 0.192(7) -0.002(5) 0.028(4) -0.010(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 Sm1 O3 2.386(4) . ? Sm1 O5 2.396(5) . ? Sm1 O7 2.402(12) . ? Sm1 O6 2.408(4) . ? Sm1 O8 2.412(8) . ? Sm1 O2 2.450(5) . ? Sm1 O4 2.464(4) . ? Sm1 O1 2.543(5) . ? Sm1 O7A 2.645(15) . ? Sm1 O3 2.681(4) 7_665 ? Sm1 C1 2.845(6) . ? Sm1 C9 2.944(6) . ? O1 C1 1.261(9) . ? O2 C1 1.241(10) . ? O3 C9 1.272(7) 7_665 ? O3 Sm1 2.681(4) 7_665 ? O4 C9 1.250(7) . ? O5 C16 1.252(8) . ? O6 C16 1.272(7) 7_665 ? O7 O7A 0.543(18) . ? O7 C17 1.252(5) . ? O7A C17 1.46(2) . ? O8 C20 1.245(5) . ? N1 C8 1.249(10) . ? N1 C14 1.417(7) 3 ? N2 C17 1.446(5) . ? N2 C19 1.449(5) . ? N2 C18 1.453(5) . ? N3 C21 1.443(5) . ? N3 C22 1.452(5) . ? N3 C20 1.458(5) . ? C1 C2 1.507(9) . ? C2 C3 1.359(11) . ? C2 C7 1.383(11) . ? C3 C4 1.384(10) . ? C3 H3 0.9300 . ? C4 C5 1.396(11) . ? C4 H4 0.9300 . ? C5 C6 1.334(12) . ? C5 C8 1.483(10) . ? C6 C7 1.398(12) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H16 0.96(2) . ? C9 O3 1.272(7) 7_665 ? C9 C10 1.509(9) . ? C10 C11 1.393(8) . ? C10 C15 1.401(8) . ? C11 C12 1.382(9) . ? C11 H11 0.9300 . ? C12 C13 1.390(8) . ? C12 C16 1.506(9) 4_644 ? C13 C14 1.413(9) . ? C13 H13 0.9300 . ? C14 C15 1.364(9) . ? C14 N1 1.417(7) 3_445 ? C15 H15 0.9300 . ? C16 O6 1.272(7) 7_665 ? C16 C12 1.506(9) 4_654 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O3 Sm1 O5 73.69(16) . . ? O3 Sm1 O7 144.2(3) . . ? O5 Sm1 O7 142.1(3) . . ? O3 Sm1 O6 80.15(16) . . ? O5 Sm1 O6 134.34(16) . . ? O7 Sm1 O6 71.8(3) . . ? O3 Sm1 O8 82.6(2) . . ? O5 Sm1 O8 135.3(2) . . ? O7 Sm1 O8 69.1(3) . . ? O6 Sm1 O8 75.1(2) . . ? O3 Sm1 O2 134.32(16) . . ? O5 Sm1 O2 78.37(19) . . ? O7 Sm1 O2 70.9(4) . . ? O6 Sm1 O2 142.61(19) . . ? O8 Sm1 O2 93.1(3) . . ? O3 Sm1 O4 124.19(15) . . ? O5 Sm1 O4 75.16(18) . . ? O7 Sm1 O4 78.6(3) . . ? O6 Sm1 O4 90.31(18) . . ? O8 Sm1 O4 147.3(2) . . ? O2 Sm1 O4 80.81(17) . . ? O3 Sm1 O1 84.57(15) . . ? O5 Sm1 O1 70.81(18) . . ? O7 Sm1 O1 104.8(3) . . ? O6 Sm1 O1 143.07(18) . . ? O8 Sm1 O1 69.7(2) . . ? O2 Sm1 O1 52.04(17) . . ? O4 Sm1 O1 125.73(15) . . ? O3 Sm1 O7A 148.9(4) . . ? O5 Sm1 O7A 135.5(4) . . ? O7 Sm1 O7A 11.1(5) . . ? O6 Sm1 O7A 70.7(4) . . ? O8 Sm1 O7A 79.8(4) . . ? O2 Sm1 O7A 72.4(4) . . ? O4 Sm1 O7A 67.7(3) . . ? O1 Sm1 O7A 112.6(4) . . ? O3 Sm1 O3 75.65(15) . 7_665 ? O5 Sm1 O3 69.65(15) . 7_665 ? O7 Sm1 O3 112.1(3) . 7_665 ? O6 Sm1 O3 67.95(16) . 7_665 ? O8 Sm1 O3 139.6(2) . 7_665 ? O2 Sm1 O3 126.31(18) . 7_665 ? O4 Sm1 O3 50.34(13) . 7_665 ? O1 Sm1 O3 139.32(17) . 7_665 ? O7A Sm1 O3 102.2(4) . 7_665 ? O3 Sm1 C1 109.76(19) . . ? O5 Sm1 C1 72.39(18) . . ? O7 Sm1 C1 87.9(4) . . ? O6 Sm1 C1 152.97(19) . . ? O8 Sm1 C1 81.2(3) . . ? O2 Sm1 C1 25.7(2) . . ? O4 Sm1 C1 103.16(19) . . ? O1 Sm1 C1 26.3(2) . . ? O7A Sm1 C1 92.7(4) . . ? O3 Sm1 C1 138.15(17) 7_665 . ? O3 Sm1 C9 100.39(16) . . ? O5 Sm1 C9 70.52(17) . . ? O7 Sm1 C9 95.4(3) . . ? O6 Sm1 C9 78.43(18) . . ? O8 Sm1 C9 152.4(2) . . ? O2 Sm1 C9 103.42(19) . . ? O4 Sm1 C9 24.75(15) . . ? O1 Sm1 C9 137.71(17) . . ? O7A Sm1 C9 84.4(3) . . ? O3 Sm1 C9 25.60(14) 7_665 . ? C1 Sm1 C9 122.17(19) . . ? C1 O1 Sm1 90.3(4) . . ? C1 O2 Sm1 95.2(4) . . ? C9 O3 Sm1 160.0(4) 7_665 . ? C9 O3 Sm1 88.9(3) 7_665 7_665 ? Sm1 O3 Sm1 104.35(15) . 7_665 ? C9 O4 Sm1 99.7(4) . . ? C16 O5 Sm1 135.2(4) . . ? C16 O6 Sm1 134.0(4) 7_665 . ? O7A O7 C17 102(3) . . ? O7A O7 Sm1 111(3) . . ? C17 O7 Sm1 129.7(11) . . ? O7 O7A C17 57(2) . . ? O7 O7A Sm1 58(2) . . ? C17 O7A Sm1 105.3(9) . . ? C20 O8 Sm1 134.0(10) . . ? C8 N1 C14 119.9(7) . 3 ? C17 N2 C19 124.8(14) . . ? C17 N2 C18 99.9(15) . . ? C19 N2 C18 135.1(16) . . ? C21 N3 C22 129.8(16) . . ? C21 N3 C20 105.3(13) . . ? C22 N3 C20 124.0(15) . . ? O2 C1 O1 122.4(6) . . ? O2 C1 C2 118.5(7) . . ? O1 C1 C2 119.1(7) . . ? O2 C1 Sm1 59.0(3) . . ? O1 C1 Sm1 63.4(3) . . ? C2 C1 Sm1 177.2(6) . . ? C3 C2 C7 118.3(7) . . ? C3 C2 C1 121.4(7) . . ? C7 C2 C1 120.3(7) . . ? C2 C3 C4 121.4(8) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 119.2(8) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 120.3(7) . . ? C6 C5 C8 118.8(8) . . ? C4 C5 C8 120.6(7) . . ? C5 C6 C7 119.9(9) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C2 C7 C6 120.9(8) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? N1 C8 C5 124.1(8) . . ? N1 C8 H16 131(6) . . ? C5 C8 H16 105(6) . . ? O4 C9 O3 121.1(6) . 7_665 ? O4 C9 C10 119.3(5) . . ? O3 C9 C10 119.6(5) 7_665 . ? O4 C9 Sm1 55.6(3) . . ? O3 C9 Sm1 65.6(3) 7_665 . ? C10 C9 Sm1 174.8(4) . . ? C11 C10 C15 120.0(6) . . ? C11 C10 C9 119.7(5) . . ? C15 C10 C9 120.3(5) . . ? C12 C11 C10 119.7(5) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.4(6) . . ? C11 C12 C16 121.0(5) . 4_644 ? C13 C12 C16 118.6(6) . 4_644 ? C12 C13 C14 119.4(6) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 120.0(5) . . ? C15 C14 N1 117.9(6) . 3_445 ? C13 C14 N1 122.1(6) . 3_445 ? C14 C15 C10 120.2(6) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? O5 C16 O6 125.5(6) . 7_665 ? O5 C16 C12 117.8(5) . 4_654 ? O6 C16 C12 116.7(6) 7_665 4_654 ? O7 C17 N2 134.3(16) . . ? O7 C17 O7A 21.3(9) . . ? N2 C17 O7A 116.1(13) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 C20 N3 114.2(13) . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.406 _refine_diff_density_min -0.933 _refine_diff_density_rms 0.143 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 -0.001 319 52 ' ' 2 0.250 0.750 0.000 190 31 ' ' 3 0.500 0.000 -0.001 319 52 ' ' 4 0.750 0.250 0.000 190 31 ' ' 5 0.250 0.250 0.500 190 31 ' ' 6 0.750 0.750 0.500 190 31 ' ' data_UCY-8 _database_code_depnum_ccdc_archive 'CCDC 916227' #TrackingRef 'UCY-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 Eu N2 O8' _chemical_formula_sum 'C19 H14 Eu N2 O8' _chemical_formula_weight 550.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -8.9294 11.1857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.255(2) _cell_length_b 12.6990(19) _cell_length_c 14.2602(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.522(8) _cell_angle_gamma 90.00 _cell_volume 5252.2(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2552 _cell_measurement_theta_min 3.0448 _cell_measurement_theta_max 66.9735 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 17.439 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.29316 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9887 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 66.98 _reflns_number_total 4665 _reflns_number_gt 3565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.1284P)^2^+18.1504P] 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 4665 _refine_ls_number_parameters 274 _refine_ls_number_restraints 51 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0718 _refine_ls_wR_factor_ref 0.2199 _refine_ls_wR_factor_gt 0.2025 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.118 _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 Eu1 Eu 0.814484(15) 0.19936(4) 0.54244(3) 0.0435(2) Uani 1 1 d . . . O1 O 0.8858(2) 0.1486(7) 0.4800(6) 0.076(2) Uani 1 1 d . . . O2 O 0.8767(3) 0.3181(6) 0.4996(6) 0.066(2) Uani 1 1 d . . . O3 O 0.7298(2) 0.1440(5) 0.4710(5) 0.0591(17) Uani 1 1 d . . . O4 O 0.7880(2) 0.0413(6) 0.4551(5) 0.0618(17) Uani 1 1 d . . . O5 O 0.7664(3) 0.1775(7) 0.6621(5) 0.072(2) Uani 1 1 d U . . O6 O 0.8014(2) 0.2427(8) 0.3769(5) 0.066(2) Uani 1 1 d . . . O7 O 0.8464(3) 0.0471(8) 0.6307(7) 0.092(3) Uani 1 1 d U . . O8 O 0.8588(3) 0.2704(8) 0.6826(7) 0.089(3) Uani 1 1 d U . . N1 N 1.0953(3) 0.3990(8) 0.3499(5) 0.056(2) Uani 1 1 d . . . N2 N 0.8863(7) 0.3558(17) 0.8183(14) 0.149(5) Uani 1 1 d U . . C1 C 0.8999(3) 0.2442(10) 0.4761(7) 0.058(3) Uani 1 1 d . . . C2 C 0.9445(3) 0.2615(10) 0.4352(8) 0.061(3) Uani 1 1 d . . . C3 C 0.9697(4) 0.1776(12) 0.4061(11) 0.084(4) Uani 1 1 d . . . H3 H 0.9582 0.1095 0.4067 0.101 Uiso 1 1 calc R . . C4 C 1.0119(5) 0.1960(10) 0.3765(12) 0.091(5) Uani 1 1 d . . . H4 H 1.0288 0.1395 0.3577 0.109 Uiso 1 1 calc R . . C5 C 1.0296(4) 0.2953(10) 0.3739(8) 0.064(3) Uani 1 1 d . . . C6 C 1.0036(4) 0.3785(11) 0.4034(8) 0.072(3) Uani 1 1 d . . . H6 H 1.0147 0.4470 0.4015 0.086 Uiso 1 1 calc R . . C7 C 0.9619(4) 0.3601(11) 0.4353(9) 0.073(3) Uani 1 1 d . . . H7 H 0.9456 0.4159 0.4571 0.088 Uiso 1 1 calc R . . C8 C 1.0764(4) 0.3126(11) 0.3460(8) 0.067(3) Uani 1 1 d D . . H16 H 1.088(4) 0.245(4) 0.336(9) 0.081 Uiso 1 1 d D . . C9 C 0.7461(3) 0.0620(8) 0.4351(7) 0.053(2) Uani 1 1 d . . . C10 C 0.7158(3) -0.0098(8) 0.3749(6) 0.049(2) Uani 1 1 d . . . C11 C 0.6694(3) -0.0184(9) 0.3845(6) 0.053(2) Uani 1 1 d . . . H11 H 0.6569 0.0246 0.4274 0.063 Uiso 1 1 calc R . . C12 C 0.6414(3) -0.0901(8) 0.3311(6) 0.051(2) Uani 1 1 d . . . C13 C 0.6593(3) -0.1497(9) 0.2617(6) 0.053(2) Uani 1 1 d . . . H13 H 0.6410 -0.1981 0.2252 0.064 Uiso 1 1 calc R . . C14 C 0.7058(3) -0.1348(9) 0.2485(6) 0.054(2) Uani 1 1 d . . . C15 C 0.7342(3) -0.0699(8) 0.3068(6) 0.050(2) Uani 1 1 d . . . H15 H 0.7654 -0.0659 0.3011 0.060 Uiso 1 1 calc R . . C16 C 0.7256(3) 0.1945(9) 0.6721(7) 0.057(3) Uani 1 1 d . . . C17 C 0.8481(10) 0.3107(19) 0.758(2) 0.144(6) Uani 1 1 d U . . C18 C 0.8656(9) 0.411(2) 0.8927(18) 0.174(7) Uani 1 1 d U . . H18A H 0.8894 0.4440 0.9357 0.261 Uiso 1 1 calc R . . H18B H 0.8490 0.3620 0.9266 0.261 Uiso 1 1 calc R . . H18C H 0.8447 0.4643 0.8645 0.261 Uiso 1 1 calc R . . C19 C 0.9340(8) 0.372(2) 0.8023(18) 0.170(6) Uani 1 1 d U . . H19A H 0.9510 0.4038 0.8573 0.254 Uiso 1 1 calc R . . H19B H 0.9348 0.4174 0.7487 0.254 Uiso 1 1 calc R . . H19C H 0.9477 0.3054 0.7903 0.254 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.0309(3) 0.0643(4) 0.0362(3) 0.0036(2) 0.0082(2) -0.0011(2) O1 0.046(4) 0.084(6) 0.105(6) 0.015(5) 0.031(4) -0.006(4) O2 0.052(4) 0.075(5) 0.077(5) -0.017(4) 0.028(4) -0.018(3) O3 0.053(4) 0.046(3) 0.084(5) -0.003(3) 0.029(3) -0.001(3) O4 0.041(3) 0.065(4) 0.081(5) -0.008(4) 0.011(3) -0.005(3) O5 0.053(3) 0.106(4) 0.060(3) 0.017(3) 0.021(3) 0.006(3) O6 0.040(4) 0.117(6) 0.043(3) 0.008(4) 0.012(3) 0.003(4) O7 0.090(4) 0.099(5) 0.085(4) 0.018(4) 0.004(4) 0.010(4) O8 0.084(4) 0.102(4) 0.077(4) -0.001(4) -0.003(3) 0.000(4) N1 0.039(4) 0.080(6) 0.051(4) -0.002(4) 0.011(3) -0.009(4) N2 0.157(6) 0.150(7) 0.138(6) -0.012(5) 0.009(4) -0.010(5) C1 0.039(5) 0.091(8) 0.048(5) 0.000(5) 0.016(4) -0.011(5) C2 0.045(5) 0.081(7) 0.058(6) 0.002(6) 0.007(4) -0.013(5) C3 0.055(7) 0.092(9) 0.112(11) -0.011(8) 0.038(7) -0.010(6) C4 0.076(9) 0.078(9) 0.130(13) -0.029(8) 0.062(9) -0.028(6) C5 0.047(6) 0.094(9) 0.056(6) -0.012(5) 0.018(5) -0.003(5) C6 0.051(6) 0.084(8) 0.082(8) -0.003(6) 0.015(5) -0.009(5) C7 0.051(6) 0.093(9) 0.079(7) -0.009(7) 0.020(5) 0.000(6) C8 0.056(7) 0.089(9) 0.060(6) -0.008(6) 0.021(5) -0.004(6) C9 0.032(4) 0.069(6) 0.061(5) 0.000(5) 0.015(4) -0.006(4) C10 0.041(4) 0.053(5) 0.054(5) -0.003(4) 0.014(4) 0.008(4) C11 0.040(4) 0.075(7) 0.045(5) -0.003(4) 0.013(4) -0.001(4) C12 0.036(4) 0.076(6) 0.044(4) -0.003(5) 0.012(3) 0.001(4) C13 0.043(5) 0.073(6) 0.046(5) -0.006(5) 0.014(4) -0.007(4) C14 0.041(5) 0.078(7) 0.043(5) -0.008(5) 0.005(4) 0.000(4) C15 0.036(4) 0.071(6) 0.045(4) 0.008(4) 0.014(3) -0.004(4) C16 0.038(5) 0.098(8) 0.037(5) 0.019(5) 0.007(4) 0.000(4) C17 0.148(7) 0.149(7) 0.137(7) -0.004(5) 0.023(5) -0.001(5) C18 0.179(8) 0.176(8) 0.169(7) -0.009(5) 0.027(5) 0.000(5) C19 0.165(7) 0.170(8) 0.173(8) -0.002(5) 0.023(5) -0.001(5) _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 Eu1 O5 2.366(7) . ? Eu1 O3 2.367(7) 7_656 ? Eu1 O6 2.405(7) . ? Eu1 O8 2.411(10) . ? Eu1 O7 2.426(9) . ? Eu1 O4 2.435(7) . ? Eu1 O1 2.459(7) . ? Eu1 O2 2.501(7) . ? Eu1 O3 2.648(7) . ? Eu1 C1 2.842(9) . ? Eu1 C9 2.930(10) . ? Eu1 Eu1 4.0199(10) 7_656 ? O1 C1 1.284(15) . ? O2 C1 1.229(14) . ? O3 C9 1.281(12) . ? O3 Eu1 2.367(7) 7_656 ? O4 C9 1.249(11) . ? O5 C16 1.238(12) . ? O6 C16 1.266(13) 7_656 ? O8 C17 1.27(3) . ? N1 C8 1.228(15) . ? N1 C12 1.415(11) 3 ? N2 C17 1.44(3) . ? N2 C19 1.46(3) . ? N2 C18 1.47(3) . ? C1 C2 1.513(13) . ? C2 C7 1.352(18) . ? C2 C3 1.390(18) . ? C3 C4 1.376(16) . ? C3 H3 0.9300 . ? C4 C5 1.365(16) . ? C4 H4 0.9300 . ? C5 C6 1.397(16) . ? C5 C8 1.492(15) . ? C6 C7 1.377(14) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H16 0.95(2) . ? C9 C10 1.468(14) . ? C10 C11 1.387(12) . ? C10 C15 1.396(12) . ? C11 C12 1.385(14) . ? C11 H11 0.9300 . ? C12 C13 1.401(13) . ? C12 N1 1.415(11) 3_445 ? C13 C14 1.409(12) . ? C13 H13 0.9300 . ? C14 C15 1.372(14) . ? C14 C16 1.504(13) 6 ? C15 H15 0.9300 . ? C16 O6 1.266(13) 7_656 ? C16 C14 1.504(13) 6_556 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O5 Eu1 O3 77.7(3) . 7_656 ? O5 Eu1 O6 134.5(2) . . ? O3 Eu1 O6 73.3(3) 7_656 . ? O5 Eu1 O8 75.6(3) . . ? O3 Eu1 O8 89.0(3) 7_656 . ? O6 Eu1 O8 136.7(3) . . ? O5 Eu1 O7 75.9(3) . . ? O3 Eu1 O7 151.7(3) 7_656 . ? O6 Eu1 O7 133.9(3) . . ? O8 Eu1 O7 74.9(3) . . ? O5 Eu1 O4 95.3(3) . . ? O3 Eu1 O4 121.1(2) 7_656 . ? O6 Eu1 O4 71.8(3) . . ? O8 Eu1 O4 146.4(3) . . ? O7 Eu1 O4 71.5(3) . . ? O5 Eu1 O1 147.5(3) . . ? O3 Eu1 O1 132.2(2) 7_656 . ? O6 Eu1 O1 74.8(3) . . ? O8 Eu1 O1 90.5(3) . . ? O7 Eu1 O1 72.1(3) . . ? O4 Eu1 O1 80.0(3) . . ? O5 Eu1 O2 140.2(3) . . ? O3 Eu1 O2 83.2(2) 7_656 . ? O6 Eu1 O2 69.5(3) . . ? O8 Eu1 O2 69.3(3) . . ? O7 Eu1 O2 111.4(3) . . ? O4 Eu1 O2 124.4(2) . . ? O1 Eu1 O2 52.4(3) . . ? O5 Eu1 O3 68.4(3) . . ? O3 Eu1 O3 73.6(2) 7_656 . ? O6 Eu1 O3 70.3(2) . . ? O8 Eu1 O3 142.5(3) . . ? O7 Eu1 O3 105.4(3) . . ? O4 Eu1 O3 50.6(2) . . ? O1 Eu1 O3 125.9(3) . . ? O2 Eu1 O3 137.8(3) . . ? O5 Eu1 C1 153.6(3) . . ? O3 Eu1 C1 107.5(3) 7_656 . ? O6 Eu1 C1 70.2(3) . . ? O8 Eu1 C1 78.5(3) . . ? O7 Eu1 C1 92.1(3) . . ? O4 Eu1 C1 103.3(3) . . ? O1 Eu1 C1 26.8(3) . . ? O2 Eu1 C1 25.6(3) . . ? O3 Eu1 C1 138.1(3) . . ? O5 Eu1 C9 82.9(3) . . ? O3 Eu1 C9 97.4(3) 7_656 . ? O6 Eu1 C9 67.3(3) . . ? O8 Eu1 C9 155.8(3) . . ? O7 Eu1 C9 89.2(3) . . ? O4 Eu1 C9 24.8(2) . . ? O1 Eu1 C9 102.0(3) . . ? O2 Eu1 C9 134.5(3) . . ? O3 Eu1 C9 25.9(2) . . ? C1 Eu1 C9 121.0(3) . . ? O5 Eu1 Eu1 68.36(19) . 7_656 ? O3 Eu1 Eu1 39.19(17) 7_656 7_656 ? O6 Eu1 Eu1 66.94(16) . 7_656 ? O8 Eu1 Eu1 120.8(2) . 7_656 ? O7 Eu1 Eu1 133.9(2) . 7_656 ? O4 Eu1 Eu1 83.48(16) . 7_656 ? O1 Eu1 Eu1 141.5(2) . 7_656 ? O2 Eu1 Eu1 114.7(2) . 7_656 ? O3 Eu1 Eu1 34.40(14) . 7_656 ? C1 Eu1 Eu1 131.8(2) . 7_656 ? C9 Eu1 Eu1 58.91(19) . 7_656 ? C1 O1 Eu1 93.4(6) . . ? C1 O2 Eu1 92.9(6) . . ? C9 O3 Eu1 151.6(7) . 7_656 ? C9 O3 Eu1 89.4(5) . . ? Eu1 O3 Eu1 106.4(2) 7_656 . ? C9 O4 Eu1 100.4(6) . . ? C16 O5 Eu1 137.4(7) . . ? C16 O6 Eu1 133.9(7) 7_656 . ? C17 O8 Eu1 133.7(15) . . ? C8 N1 C12 121.0(10) . 3 ? C17 N2 C19 130(2) . . ? C17 N2 C18 105(2) . . ? C19 N2 C18 123(2) . . ? O2 C1 O1 121.2(8) . . ? O2 C1 C2 121.8(11) . . ? O1 C1 C2 116.8(10) . . ? O2 C1 Eu1 61.5(5) . . ? O1 C1 Eu1 59.7(5) . . ? C2 C1 Eu1 175.7(8) . . ? C7 C2 C3 119.6(10) . . ? C7 C2 C1 118.6(11) . . ? C3 C2 C1 121.5(11) . . ? C4 C3 C2 119.7(13) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 121.5(13) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.0(10) . . ? C4 C5 C8 120.4(11) . . ? C6 C5 C8 121.5(11) . . ? C7 C6 C5 120.7(12) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C2 C7 C6 120.5(12) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? N1 C8 C5 123.0(11) . . ? N1 C8 H16 130(8) . . ? C5 C8 H16 106(8) . . ? O4 C9 O3 119.1(9) . . ? O4 C9 C10 120.1(9) . . ? O3 C9 C10 120.7(8) . . ? O4 C9 Eu1 54.8(5) . . ? O3 C9 Eu1 64.6(5) . . ? C10 C9 Eu1 173.7(6) . . ? C11 C10 C15 119.8(9) . . ? C11 C10 C9 121.0(8) . . ? C15 C10 C9 119.3(8) . . ? C12 C11 C10 120.9(9) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 119.7(8) . . ? C11 C12 N1 118.0(8) . 3_445 ? C13 C12 N1 122.3(9) . 3_445 ? C12 C13 C14 118.6(9) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 121.1(9) . . ? C15 C14 C16 118.8(8) . 6 ? C13 C14 C16 120.0(9) . 6 ? C14 C15 C10 119.6(8) . . ? C14 C15 H15 120.2 . . ? C10 C15 H15 120.2 . . ? O5 C16 O6 125.9(9) . 7_656 ? O5 C16 C14 117.7(9) . 6_556 ? O6 C16 C14 116.4(8) 7_656 6_556 ? O8 C17 N2 114(2) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 66.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.382 _refine_diff_density_min -1.295 _refine_diff_density_rms 0.145 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.002 -0.033 0.240 1832 519 ' ' data_UCY-9 _database_code_depnum_ccdc_archive 'CCDC 916228' #TrackingRef 'UCY-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C82 H68 Gd4 N10 O31, 4(O0.25)' _chemical_formula_sum 'C82 H68 Gd4 N10 O32' _chemical_formula_weight 2334.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Gd Gd -8.8380 11.9157 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.747(2) _cell_length_b 14.4478(10) _cell_length_c 13.3233(8) _cell_angle_alpha 90.00 _cell_angle_beta 99.760(7) _cell_angle_gamma 90.00 _cell_volume 5453.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4416 _cell_measurement_theta_min 3.1170 _cell_measurement_theta_max 70.8664 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2284 _exptl_absorpt_coefficient_mu 16.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.33348 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9376 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0683 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 67.00 _reflns_number_total 4854 _reflns_number_gt 3806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.1443P)^2^+15.0849P] 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 4854 _refine_ls_number_parameters 329 _refine_ls_number_restraints 106 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0750 _refine_ls_wR_factor_ref 0.2199 _refine_ls_wR_factor_gt 0.2065 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.065 _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 Gd1 Gd 0.182860(15) 0.71325(3) 0.45891(4) 0.0314(2) Uani 1 1 d . . . O1 O 0.1091(3) 0.6832(6) 0.5150(8) 0.063(2) Uani 1 1 d . . . O2 O 0.1225(3) 0.8316(5) 0.4971(7) 0.060(2) Uani 1 1 d . . . O3 O 0.2061(2) 0.5716(4) 0.5532(5) 0.0433(15) Uani 1 1 d . . . O4 O 0.2312(2) 0.8459(4) 0.4589(5) 0.0406(15) Uani 1 1 d . . . O5 O 0.2014(2) 0.7601(5) 0.6298(5) 0.0389(14) Uani 1 1 d . . . O6 O 0.2279(2) 0.6698(5) 0.3310(5) 0.0462(17) Uani 1 1 d . . . O7 O 0.1430(4) 0.5894(8) 0.3601(8) 0.057(2) Uani 0.75 1 d PDU . . O7A O 0.1494(14) 0.537(3) 0.359(3) 0.071(4) Uani 0.25 1 d PU . . O8 O 0.1400(5) 0.7797(12) 0.3066(14) 0.066(3) Uani 0.75 1 d PDU . . O8A O 0.153(2) 0.788(4) 0.302(5) 0.074(5) Uani 0.25 1 d PU . . N1 N -0.0983(3) 0.9190(6) 0.6476(7) 0.050(2) Uani 1 1 d . . . N2 N 0.1187(5) 0.5138(10) 0.1938(11) 0.071(3) Uani 0.75 1 d PDU . . N3 N 0.1205(7) 0.8789(13) 0.1748(14) 0.095(4) Uani 0.75 1 d PDU . . C1 C 0.0972(3) 0.7667(8) 0.5217(8) 0.045(2) Uani 1 1 d . . . C2 C 0.0521(4) 0.7880(7) 0.5563(9) 0.047(2) Uani 1 1 d . . . C3 C 0.0226(5) 0.7146(9) 0.5771(14) 0.077(5) Uani 1 1 d . . . H3 H 0.0317 0.6535 0.5701 0.092 Uiso 1 1 calc R . . C4 C -0.0203(5) 0.7345(11) 0.6082(16) 0.097(6) Uani 1 1 d . . . H4 H -0.0397 0.6862 0.6221 0.116 Uiso 1 1 calc R . . C5 C -0.0342(4) 0.8221(9) 0.6183(10) 0.059(3) Uani 1 1 d . . . C6 C -0.0053(4) 0.8952(9) 0.5977(9) 0.060(3) Uani 1 1 d . . . H6 H -0.0145 0.9561 0.6058 0.072 Uiso 1 1 calc R . . C7 C 0.0368(4) 0.8766(8) 0.5652(10) 0.057(3) Uani 1 1 d . . . H7 H 0.0552 0.9255 0.5491 0.069 Uiso 1 1 calc R . . C8 C -0.0812(4) 0.8387(10) 0.6470(9) 0.060(3) Uani 1 1 d D . . H16 H -0.098(4) 0.788(6) 0.670(11) 0.072 Uiso 1 1 d D . . C9 C 0.2503(3) 0.5819(6) 0.5731(7) 0.0335(18) Uani 1 1 d . . . C10 C 0.2803(3) 0.5081(6) 0.6276(7) 0.0368(19) Uani 1 1 d . . . C11 C 0.3273(3) 0.4983(6) 0.6153(8) 0.040(2) Uani 1 1 d . . . H11 H 0.3404 0.5394 0.5743 0.048 Uiso 1 1 calc R . . C12 C 0.3546(3) 0.4257(7) 0.6655(8) 0.042(2) Uani 1 1 d . . . C13 C 0.3364(3) 0.3698(6) 0.7341(7) 0.038(2) Uani 1 1 d . . . H13 H 0.3555 0.3253 0.7712 0.046 Uiso 1 1 calc R . . C14 C 0.2894(3) 0.3800(6) 0.7476(7) 0.0353(19) Uani 1 1 d . . . C15 C 0.2610(3) 0.4473(6) 0.6923(7) 0.037(2) Uani 1 1 d . . . H15 H 0.2293 0.4520 0.6983 0.044 Uiso 1 1 calc R . . C16 C 0.2297(4) 0.8194(7) 0.6804(8) 0.043(2) Uani 1 1 d . . . C17 C 0.1338(7) 0.5865(13) 0.2606(14) 0.075(3) Uani 0.75 1 d PDU . . C18 C 0.1210(9) 0.4262(15) 0.2502(18) 0.100(5) Uani 0.75 1 d PDU . . H18A H 0.1106 0.3765 0.2039 0.150 Uiso 0.75 1 calc PR . . H18B H 0.1010 0.4297 0.3009 0.150 Uiso 0.75 1 calc PR . . H18C H 0.1530 0.4150 0.2826 0.150 Uiso 0.75 1 calc PR . . C19 C 0.1017(8) 0.5248(15) 0.0886(14) 0.084(4) Uani 0.75 1 d PDU . . H19A H 0.0928 0.4655 0.0587 0.126 Uiso 0.75 1 calc PR . . H19B H 0.1259 0.5515 0.0564 0.126 Uiso 0.75 1 calc PR . . H19C H 0.0746 0.5649 0.0792 0.126 Uiso 0.75 1 calc PR . . C20 C 0.1525(8) 0.8206(17) 0.2427(18) 0.088(4) Uani 0.75 1 d PDU . . C21 C 0.0745(8) 0.8904(17) 0.1961(18) 0.100(5) Uani 0.75 1 d PDU . . H21A H 0.0696 0.8483 0.2490 0.150 Uiso 0.75 1 calc PR . . H21B H 0.0520 0.8779 0.1358 0.150 Uiso 0.75 1 calc PR . . H21C H 0.0707 0.9528 0.2179 0.150 Uiso 0.75 1 calc PR . . C22 C 0.1413(9) 0.9243(17) 0.1064(18) 0.102(5) Uani 0.75 1 d PDU . . H22A H 0.1729 0.9015 0.1092 0.153 Uiso 0.75 1 calc PR . . H22B H 0.1423 0.9892 0.1218 0.153 Uiso 0.75 1 calc PR . . H22C H 0.1236 0.9145 0.0394 0.153 Uiso 0.75 1 calc PR . . 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 Gd1 0.0203(3) 0.0343(3) 0.0423(3) 0.0000(2) 0.0128(2) 0.00120(17) O1 0.034(4) 0.051(4) 0.107(7) -0.014(5) 0.025(4) 0.002(3) O2 0.049(4) 0.053(5) 0.086(6) 0.017(4) 0.033(4) 0.016(3) O3 0.026(3) 0.040(4) 0.068(4) 0.001(3) 0.022(3) -0.001(3) O4 0.034(3) 0.036(3) 0.060(4) -0.002(3) 0.032(3) 0.007(3) O5 0.029(3) 0.046(4) 0.046(4) -0.010(3) 0.019(3) -0.006(3) O6 0.025(3) 0.059(4) 0.060(4) -0.026(3) 0.022(3) -0.008(3) O7 0.046(4) 0.059(4) 0.065(3) -0.005(4) 0.009(3) -0.016(4) O7A 0.070(7) 0.069(5) 0.073(5) -0.002(4) 0.013(5) 0.002(5) O8 0.065(5) 0.068(5) 0.061(4) -0.006(3) 0.005(4) 0.009(4) O8A 0.074(6) 0.073(7) 0.076(6) -0.003(5) 0.011(5) -0.001(5) N1 0.033(4) 0.062(6) 0.058(5) 0.009(4) 0.018(4) 0.013(4) N2 0.069(5) 0.073(4) 0.072(4) -0.009(3) 0.014(4) 0.002(4) N3 0.100(5) 0.090(6) 0.093(5) 0.009(4) 0.011(4) 0.004(4) C1 0.029(5) 0.062(6) 0.049(5) -0.006(5) 0.025(4) -0.010(4) C2 0.032(5) 0.054(7) 0.056(6) 0.013(5) 0.014(4) 0.006(4) C3 0.048(7) 0.065(9) 0.126(13) 0.021(7) 0.043(8) 0.006(5) C4 0.059(9) 0.071(9) 0.174(18) 0.039(10) 0.059(10) 0.005(7) C5 0.049(6) 0.065(7) 0.068(7) 0.018(6) 0.023(5) 0.011(5) C6 0.054(6) 0.060(7) 0.074(8) 0.017(6) 0.031(6) 0.007(5) C7 0.037(5) 0.059(7) 0.079(8) -0.001(6) 0.018(5) 0.001(5) C8 0.047(6) 0.079(9) 0.059(7) 0.017(6) 0.021(5) 0.006(6) C9 0.028(4) 0.030(4) 0.046(5) 0.000(4) 0.017(3) 0.003(3) C10 0.029(4) 0.034(5) 0.049(5) -0.002(4) 0.013(4) -0.002(3) C11 0.033(4) 0.034(5) 0.060(6) 0.010(4) 0.025(4) 0.006(4) C12 0.025(4) 0.053(6) 0.052(5) 0.009(5) 0.017(4) 0.004(4) C13 0.033(4) 0.042(5) 0.044(5) 0.013(4) 0.018(4) 0.002(4) C14 0.029(4) 0.043(5) 0.036(4) 0.001(4) 0.011(3) 0.000(3) C15 0.028(4) 0.040(5) 0.048(5) -0.003(4) 0.019(4) 0.002(4) C16 0.043(5) 0.039(5) 0.053(6) -0.009(4) 0.023(4) -0.004(4) C17 0.075(6) 0.080(5) 0.070(3) -0.004(3) 0.013(4) 0.002(4) C18 0.108(7) 0.091(5) 0.101(6) 0.010(4) 0.019(5) -0.004(5) C19 0.086(6) 0.085(6) 0.080(4) -0.005(4) 0.011(4) -0.002(5) C20 0.090(5) 0.090(6) 0.083(5) 0.002(4) 0.014(4) -0.005(4) C21 0.100(5) 0.100(7) 0.099(7) 0.000(5) 0.013(4) 0.000(4) C22 0.107(6) 0.101(7) 0.098(6) 0.008(4) 0.016(4) 0.002(5) _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 Gd1 O5 2.348(6) . ? Gd1 O4 2.367(6) . ? Gd1 O8A 2.38(7) . ? Gd1 O8 2.389(17) . ? Gd1 O6 2.392(6) . ? Gd1 O7 2.395(11) . ? Gd1 O1 2.404(7) . ? Gd1 O3 2.435(7) . ? Gd1 O2 2.548(7) . ? Gd1 O4 2.669(6) 7_566 ? Gd1 C1 2.838(9) . ? Gd1 C9 2.945(9) . ? O1 C1 1.261(14) . ? O2 C1 1.263(13) . ? O3 C9 1.263(10) . ? O4 C9 1.277(10) 7_566 ? O4 Gd1 2.669(6) 7_566 ? O5 C16 1.290(12) . ? O6 C16 1.263(11) 7_566 ? O7 O7A 0.78(4) . ? O7 C17 1.308(19) . ? O7A C17 1.49(4) . ? O8 C20 1.14(3) . ? O8A C20 0.92(6) . ? N1 C8 1.262(15) . ? N1 C12 1.415(11) 3_455 ? N2 C17 1.40(2) . ? N2 C19 1.41(2) . ? N2 C18 1.47(2) . ? N3 C22 1.34(2) . ? N3 C21 1.41(3) . ? N3 C20 1.45(3) . ? C1 C2 1.481(14) . ? C2 C7 1.365(15) . ? C2 C3 1.415(16) . ? C3 C4 1.397(19) . ? C3 H3 0.9300 . ? C4 C5 1.34(2) . ? C4 H4 0.9300 . ? C5 C6 1.399(17) . ? C5 C8 1.485(15) . ? C6 C7 1.380(15) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H16 0.95(2) . ? C9 O4 1.277(10) 7_566 ? C9 C10 1.481(12) . ? C10 C11 1.395(12) . ? C10 C15 1.409(13) . ? C11 C12 1.410(13) . ? C11 H11 0.9300 . ? C12 C13 1.387(12) . ? C12 N1 1.415(11) 3_545 ? C13 C14 1.402(12) . ? C13 H13 0.9300 . ? C14 C15 1.396(13) . ? C14 C16 1.472(12) 4_546 ? C15 H15 0.9300 . ? C16 O6 1.264(11) 7_566 ? C16 C14 1.472(12) 4_556 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O5 Gd1 O4 74.3(2) . . ? O5 Gd1 O8A 135.3(16) . . ? O4 Gd1 O8A 75.8(14) . . ? O5 Gd1 O8 135.0(5) . . ? O4 Gd1 O8 83.8(4) . . ? O8A Gd1 O8 10.0(15) . . ? O5 Gd1 O6 134.8(2) . . ? O4 Gd1 O6 79.9(2) . . ? O8A Gd1 O6 69.4(16) . . ? O8 Gd1 O6 76.4(4) . . ? O5 Gd1 O7 139.2(3) . . ? O4 Gd1 O7 146.2(3) . . ? O8A Gd1 O7 77.8(15) . . ? O8 Gd1 O7 72.8(5) . . ? O6 Gd1 O7 71.3(3) . . ? O5 Gd1 O1 79.5(3) . . ? O4 Gd1 O1 134.0(2) . . ? O8A Gd1 O1 98.8(14) . . ? O8 Gd1 O1 88.9(4) . . ? O6 Gd1 O1 141.9(3) . . ? O7 Gd1 O1 70.8(3) . . ? O5 Gd1 O3 75.2(2) . . ? O4 Gd1 O3 124.8(2) . . ? O8A Gd1 O3 149.3(15) . . ? O8 Gd1 O3 146.4(4) . . ? O6 Gd1 O3 90.7(2) . . ? O7 Gd1 O3 73.7(3) . . ? O1 Gd1 O3 82.4(2) . . ? O5 Gd1 O2 70.3(3) . . ? O4 Gd1 O2 82.9(2) . . ? O8A Gd1 O2 73.6(16) . . ? O8 Gd1 O2 68.2(5) . . ? O6 Gd1 O2 142.0(3) . . ? O7 Gd1 O2 109.4(3) . . ? O1 Gd1 O2 52.6(3) . . ? O3 Gd1 O2 126.7(2) . . ? O5 Gd1 O4 69.7(2) . 7_566 ? O4 Gd1 O4 75.9(2) . 7_566 ? O8A Gd1 O4 132.3(15) . 7_566 ? O8 Gd1 O4 141.8(4) . 7_566 ? O6 Gd1 O4 68.4(2) . 7_566 ? O7 Gd1 O4 108.0(3) . 7_566 ? O1 Gd1 O4 128.3(3) . 7_566 ? O3 Gd1 O4 50.60(19) . 7_566 ? O2 Gd1 O4 138.4(3) . 7_566 ? O5 Gd1 C1 72.6(3) . . ? O4 Gd1 C1 108.5(3) . . ? O8A Gd1 C1 86.4(15) . . ? O8 Gd1 C1 78.0(4) . . ? O6 Gd1 C1 152.0(3) . . ? O7 Gd1 C1 90.4(3) . . ? O1 Gd1 C1 26.2(3) . . ? O3 Gd1 C1 104.6(3) . . ? O2 Gd1 C1 26.4(3) . . ? O4 Gd1 C1 139.1(3) 7_566 . ? O5 Gd1 C9 70.3(2) . . ? O4 Gd1 C9 100.8(2) . . ? O8A Gd1 C9 148.4(16) . . ? O8 Gd1 C9 153.8(4) . . ? O6 Gd1 C9 79.1(2) . . ? O7 Gd1 C9 90.8(3) . . ? O1 Gd1 C9 105.1(3) . . ? O3 Gd1 C9 24.9(2) . . ? O2 Gd1 C9 137.7(3) . . ? O4 Gd1 C9 25.7(2) 7_566 . ? C1 Gd1 C9 123.4(3) . . ? C1 O1 Gd1 96.5(6) . . ? C1 O2 Gd1 89.7(6) . . ? C9 O3 Gd1 100.8(5) . . ? C9 O4 Gd1 159.9(6) 7_566 . ? C9 O4 Gd1 89.3(5) 7_566 7_566 ? Gd1 O4 Gd1 104.1(2) . 7_566 ? C16 O5 Gd1 135.8(6) . . ? C16 O6 Gd1 134.7(6) 7_566 . ? O7A O7 C17 87(3) . . ? O7A O7 Gd1 130(3) . . ? C17 O7 Gd1 125.2(11) . . ? O7 O7A C17 61(3) . . ? C20 O8 Gd1 131.1(16) . . ? C20 O8A Gd1 161(5) . . ? C8 N1 C12 116.8(10) . 3_455 ? C17 N2 C19 124.4(16) . . ? C17 N2 C18 109.9(16) . . ? C19 N2 C18 125.7(17) . . ? C22 N3 C21 128(2) . . ? C22 N3 C20 114(2) . . ? C21 N3 C20 117.5(19) . . ? O1 C1 O2 121.2(9) . . ? O1 C1 C2 118.8(9) . . ? O2 C1 C2 120.0(10) . . ? O1 C1 Gd1 57.3(5) . . ? O2 C1 Gd1 63.9(5) . . ? C2 C1 Gd1 176.1(8) . . ? C7 C2 C3 118.2(10) . . ? C7 C2 C1 122.3(10) . . ? C3 C2 C1 119.4(10) . . ? C4 C3 C2 119.6(12) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 121.1(13) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 119.9(11) . . ? C4 C5 C8 118.5(12) . . ? C6 C5 C8 121.6(12) . . ? C7 C6 C5 119.7(12) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C2 C7 C6 121.6(11) . . ? C2 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? N1 C8 C5 121.6(11) . . ? N1 C8 H16 119(8) . . ? C5 C8 H16 119(8) . . ? O3 C9 O4 119.3(8) . 7_566 ? O3 C9 C10 119.9(8) . . ? O4 C9 C10 120.7(7) 7_566 . ? O3 C9 Gd1 54.3(5) . . ? O4 C9 Gd1 65.0(5) 7_566 . ? C10 C9 Gd1 173.8(6) . . ? C11 C10 C15 119.8(8) . . ? C11 C10 C9 120.6(8) . . ? C15 C10 C9 119.5(8) . . ? C10 C11 C12 119.6(8) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 120.2(8) . . ? C13 C12 N1 123.3(9) . 3_545 ? C11 C12 N1 116.3(8) . 3_545 ? C12 C13 C14 120.1(8) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.8(8) . . ? C15 C14 C16 120.6(8) . 4_546 ? C13 C14 C16 119.6(8) . 4_546 ? C14 C15 C10 120.1(8) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? O6 C16 O5 123.7(9) 7_566 . ? O6 C16 C14 118.6(9) 7_566 4_556 ? O5 C16 C14 117.7(8) . 4_556 ? O7 C17 N2 131.0(18) . . ? O7 C17 O7A 31.6(15) . . ? N2 C17 O7A 102(2) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8A C20 O8 20(4) . . ? O8A C20 N3 140(5) . . ? O8 C20 N3 121(2) . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.004 _refine_diff_density_min -1.671 _refine_diff_density_rms 0.181 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 -0.001 301 80 ' ' 2 0.251 0.750 -0.001 192 52 ' ' 3 0.500 0.001 -0.001 300 80 ' ' 4 0.750 0.250 0.000 190 51 ' ' 5 0.250 0.250 0.500 190 51 ' ' 6 0.750 0.750 0.500 190 51 ' ' data_UCY-10 _database_code_depnum_ccdc_archive 'CCDC 916229' #TrackingRef 'UCY-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 N2 O8 Tb' _chemical_formula_sum 'C19 H14 N2 O8 Tb' _chemical_formula_weight 557.24 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' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.157(2) _cell_length_b 13.0903(12) _cell_length_c 13.9533(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.576(6) _cell_angle_gamma 90.00 _cell_volume 5279.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2740 _cell_measurement_theta_min 2.9395 _cell_measurement_theta_max 28.8789 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 2.717 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.60787 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13876 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4650 _reflns_number_gt 3344 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0697P)^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 4650 _refine_ls_number_parameters 274 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.966 _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 Tb1 Tb 0.814461(10) 0.29771(3) 0.54105(2) 0.03262(14) Uani 1 1 d . . . O1 O 0.87609(17) 0.1807(4) 0.5001(4) 0.0498(14) Uani 1 1 d . . . O2 O 0.88509(17) 0.3453(5) 0.4757(4) 0.0574(15) Uani 1 1 d . . . O3 O 0.72912(15) 0.3515(4) 0.4675(3) 0.0400(12) Uani 1 1 d . . . O4 O 0.78871(15) 0.4508(4) 0.4544(4) 0.0440(12) Uani 1 1 d . . . O5 O 0.79997(15) 0.2535(4) 0.3745(3) 0.0412(12) Uani 1 1 d . . . O6 O 0.76715(16) 0.3287(5) 0.6611(4) 0.0564(15) Uani 1 1 d . . . O7 O 0.8558(2) 0.2286(6) 0.6836(5) 0.086(2) Uani 1 1 d DU . . O8 O 0.8500(2) 0.4417(5) 0.6337(4) 0.079(2) Uani 1 1 d . . . N1 N 1.09554(18) 0.0939(5) 0.3527(4) 0.0433(15) Uani 1 1 d . . . N2 N 0.8823(4) 0.1393(9) 0.8178(8) 0.137(3) Uani 1 1 d DU . . C1 C 0.8988(2) 0.2537(7) 0.4732(5) 0.0439(18) Uani 1 1 d . . . C2 C 0.9444(2) 0.2344(6) 0.4356(5) 0.0419(18) Uani 1 1 d . . . C3 C 0.9617(2) 0.1380(7) 0.4362(5) 0.050(2) Uani 1 1 d . . . H3 H 0.9450 0.0841 0.4576 0.060 Uiso 1 1 calc R . . C4 C 1.0040(2) 0.1197(7) 0.4053(5) 0.050(2) Uani 1 1 d . . . H4 H 1.0153 0.0532 0.4052 0.061 Uiso 1 1 calc R . . C5 C 1.0291(3) 0.1968(7) 0.3751(6) 0.049(2) Uani 1 1 d . . . C6 C 1.0120(3) 0.2943(7) 0.3723(8) 0.075(3) Uani 1 1 d . . . H6 H 1.0290 0.3482 0.3515 0.090 Uiso 1 1 calc R . . C7 C 0.9682(3) 0.3116(7) 0.4014(7) 0.071(3) Uani 1 1 d . . . H7 H 0.9555 0.3769 0.3970 0.085 Uiso 1 1 calc R . . C8 C 1.0766(3) 0.1828(8) 0.3474(6) 0.055(2) Uani 1 1 d D . . C9 C 0.7463(2) 0.4325(6) 0.4350(5) 0.0379(17) Uani 1 1 d . . . C10 C 0.7157(2) 0.5051(6) 0.3749(4) 0.0357(16) Uani 1 1 d . . . C11 C 0.6689(2) 0.5150(5) 0.3852(5) 0.0357(16) Uani 1 1 d . . . H11 H 0.6562 0.4732 0.4287 0.043 Uiso 1 1 calc R . . C12 C 0.6416(2) 0.5848(6) 0.3326(5) 0.0398(18) Uani 1 1 d . . . C13 C 0.6599(2) 0.6431(6) 0.2632(5) 0.0382(17) Uani 1 1 d . . . H13 H 0.6411 0.6892 0.2255 0.046 Uiso 1 1 calc R . . C14 C 0.7064(2) 0.6322(6) 0.2502(4) 0.0384(18) Uani 1 1 d . . . C15 C 0.7345(2) 0.5658(6) 0.3082(4) 0.0374(17) Uani 1 1 d . . . H15 H 0.7659 0.5616 0.3027 0.045 Uiso 1 1 calc R . . C16 C 0.7743(2) 0.1910(6) 0.3276(5) 0.0401(19) Uani 1 1 d . . . C17 C 0.8450(5) 0.1931(11) 0.7601(8) 0.141(4) Uani 1 1 d DU . . C18 C 0.9297(4) 0.1319(12) 0.7981(11) 0.151(4) Uani 1 1 d DU . . H18A H 0.9476 0.0945 0.8491 0.227 Uiso 1 1 calc R . . H18B H 0.9424 0.1993 0.7944 0.227 Uiso 1 1 calc R . . H18C H 0.9305 0.0972 0.7378 0.227 Uiso 1 1 calc R . . C19 C 0.8649(5) 0.0825(11) 0.8944(9) 0.149(4) Uani 1 1 d DU . . H19A H 0.8901 0.0492 0.9333 0.223 Uiso 1 1 calc R . . H19B H 0.8431 0.0322 0.8667 0.223 Uiso 1 1 calc R . . H19C H 0.8499 0.1286 0.9339 0.223 Uiso 1 1 calc R . . H16 H 1.083(5) 0.246(7) 0.309(9) 0.179 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 Tb1 0.01888(18) 0.0482(2) 0.0329(2) -0.00173(16) 0.01139(13) 0.00241(16) O1 0.030(3) 0.063(4) 0.062(3) 0.016(3) 0.028(2) 0.010(3) O2 0.032(3) 0.055(4) 0.092(4) -0.016(3) 0.033(3) -0.002(3) O3 0.030(3) 0.042(3) 0.052(3) 0.005(2) 0.020(2) 0.008(2) O4 0.025(2) 0.039(3) 0.069(3) 0.006(3) 0.011(2) 0.002(2) O5 0.027(2) 0.069(3) 0.028(2) -0.010(3) 0.010(2) -0.003(3) O6 0.026(3) 0.098(4) 0.049(3) -0.032(3) 0.020(2) -0.009(3) O7 0.064(4) 0.112(6) 0.079(4) -0.026(4) 0.000(3) 0.019(4) O8 0.063(4) 0.099(5) 0.076(4) -0.041(4) 0.011(3) -0.038(4) N1 0.024(3) 0.065(4) 0.045(3) 0.012(3) 0.017(2) 0.009(3) N2 0.144(4) 0.140(5) 0.123(4) 0.007(3) 0.009(3) 0.008(3) C1 0.024(4) 0.067(5) 0.041(4) 0.000(4) 0.004(3) 0.005(4) C2 0.029(4) 0.057(5) 0.042(4) 0.006(4) 0.017(3) 0.010(4) C3 0.030(4) 0.065(6) 0.060(5) -0.001(4) 0.021(3) -0.004(4) C4 0.031(4) 0.058(5) 0.064(5) 0.006(4) 0.014(3) 0.008(4) C5 0.033(4) 0.065(6) 0.054(5) 0.008(4) 0.018(3) 0.007(4) C6 0.047(5) 0.069(6) 0.121(8) 0.028(6) 0.056(5) 0.019(5) C7 0.043(5) 0.067(6) 0.112(8) 0.003(6) 0.042(5) 0.003(5) C8 0.032(4) 0.087(7) 0.048(5) 0.010(5) 0.012(3) 0.001(5) C9 0.029(4) 0.048(5) 0.041(4) 0.002(4) 0.022(3) 0.006(4) C10 0.025(3) 0.047(4) 0.038(4) -0.008(3) 0.015(3) 0.005(3) C11 0.023(3) 0.045(4) 0.044(4) 0.005(3) 0.021(3) -0.004(3) C12 0.024(3) 0.061(5) 0.038(4) 0.006(4) 0.016(3) 0.008(4) C13 0.028(3) 0.056(5) 0.034(4) 0.002(3) 0.013(3) 0.003(4) C14 0.029(3) 0.061(5) 0.028(3) -0.003(3) 0.014(3) -0.004(4) C15 0.021(3) 0.057(5) 0.036(4) 0.003(3) 0.011(3) 0.000(3) C16 0.025(3) 0.071(6) 0.026(3) -0.011(4) 0.012(3) -0.001(4) C17 0.145(5) 0.146(5) 0.133(5) 0.009(4) 0.019(3) 0.003(4) C18 0.150(4) 0.152(6) 0.152(5) 0.003(4) 0.023(4) 0.001(4) C19 0.153(5) 0.150(5) 0.145(5) 0.010(4) 0.020(3) 0.000(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 Tb1 O3 2.324(5) 7_656 ? Tb1 O6 2.341(5) . ? Tb1 O7 2.365(7) . ? Tb1 O5 2.378(4) . ? Tb1 O4 2.409(5) . ? Tb1 O8 2.438(5) . ? Tb1 O2 2.440(5) . ? Tb1 O1 2.484(5) . ? Tb1 O3 2.658(4) . ? Tb1 C1 2.808(7) . ? Tb1 C9 2.911(7) . ? Tb1 Tb1 3.9833(6) 7_656 ? O1 C1 1.247(10) . ? O2 C1 1.266(10) . ? O3 C9 1.282(8) . ? O3 Tb1 2.324(5) 7_656 ? O4 C9 1.253(8) . ? O5 C16 1.237(8) . ? O6 C16 1.266(8) 7_656 ? O7 C17 1.242(5) . ? N1 C8 1.286(10) . ? N1 C12 1.412(8) 3_545 ? N2 C19 1.448(5) . ? N2 C18 1.446(5) . ? N2 C17 1.449(5) . ? C1 C2 1.515(10) . ? C2 C7 1.348(11) . ? C2 C3 1.358(11) . ? C3 C4 1.379(10) . ? C3 H3 0.9300 . ? C4 C5 1.347(11) . ? C4 H4 0.9300 . ? C5 C6 1.369(11) . ? C5 C8 1.497(10) . ? C6 C7 1.410(11) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H16 1.01(5) . ? C9 C10 1.486(10) . ? C10 C15 1.390(9) . ? C10 C11 1.396(8) . ? C11 C12 1.361(9) . ? C11 H11 0.9300 . ? C12 C13 1.393(9) . ? C12 N1 1.412(8) 3_455 ? C13 C14 1.400(9) . ? C13 H13 0.9300 . ? C14 C15 1.382(9) . ? C14 C16 1.499(9) 4_655 ? C15 H15 0.9300 . ? C16 O6 1.266(8) 7_656 ? C16 C14 1.499(9) 4_645 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O3 Tb1 O6 79.21(18) 7_656 . ? O3 Tb1 O7 86.4(2) 7_656 . ? O6 Tb1 O7 75.4(2) . . ? O3 Tb1 O5 73.74(17) 7_656 . ? O6 Tb1 O5 134.09(16) . . ? O7 Tb1 O5 137.2(2) . . ? O3 Tb1 O4 122.75(15) 7_656 . ? O6 Tb1 O4 92.34(19) . . ? O7 Tb1 O4 146.2(2) . . ? O5 Tb1 O4 73.04(18) . . ? O3 Tb1 O8 150.25(19) 7_656 . ? O6 Tb1 O8 74.72(19) . . ? O7 Tb1 O8 73.5(2) . . ? O5 Tb1 O8 135.6(2) . . ? O4 Tb1 O8 72.9(2) . . ? O3 Tb1 O2 132.67(17) 7_656 . ? O6 Tb1 O2 145.98(19) . . ? O7 Tb1 O2 92.9(2) . . ? O5 Tb1 O2 75.33(17) . . ? O4 Tb1 O2 79.78(18) . . ? O8 Tb1 O2 71.3(2) . . ? O3 Tb1 O1 82.96(17) 7_656 . ? O6 Tb1 O1 141.60(19) . . ? O7 Tb1 O1 69.8(2) . . ? O5 Tb1 O1 70.48(17) . . ? O4 Tb1 O1 125.76(17) . . ? O8 Tb1 O1 109.2(2) . . ? O2 Tb1 O1 53.11(18) . . ? O3 Tb1 O3 74.03(18) 7_656 . ? O6 Tb1 O3 67.70(16) . . ? O7 Tb1 O3 140.6(2) . . ? O5 Tb1 O3 69.54(15) . . ? O4 Tb1 O3 51.10(15) . . ? O8 Tb1 O3 108.14(19) . . ? O2 Tb1 O3 125.54(17) . . ? O1 Tb1 O3 137.98(16) . . ? O3 Tb1 C1 107.9(2) 7_656 . ? O6 Tb1 C1 154.33(19) . . ? O7 Tb1 C1 80.4(2) . . ? O5 Tb1 C1 70.79(18) . . ? O4 Tb1 C1 103.3(2) . . ? O8 Tb1 C1 90.4(2) . . ? O2 Tb1 C1 26.7(2) . . ? O1 Tb1 C1 26.4(2) . . ? O3 Tb1 C1 137.78(17) . . ? O3 Tb1 C9 98.71(19) 7_656 . ? O6 Tb1 C9 80.29(18) . . ? O7 Tb1 C9 153.8(2) . . ? O5 Tb1 C9 68.26(18) . . ? O4 Tb1 C9 25.03(17) . . ? O8 Tb1 C9 90.9(2) . . ? O2 Tb1 C9 102.03(19) . . ? O1 Tb1 C9 136.28(17) . . ? O3 Tb1 C9 26.11(16) . . ? C1 Tb1 C9 121.5(2) . . ? O3 Tb1 Tb1 39.91(11) 7_656 7_656 ? O6 Tb1 Tb1 68.75(12) . 7_656 ? O7 Tb1 Tb1 118.61(19) . 7_656 ? O5 Tb1 Tb1 66.63(11) . 7_656 ? O4 Tb1 Tb1 84.07(11) . 7_656 ? O8 Tb1 Tb1 135.59(15) . 7_656 ? O2 Tb1 Tb1 141.57(13) . 7_656 ? O1 Tb1 Tb1 115.11(13) . 7_656 ? O3 Tb1 Tb1 34.12(11) . 7_656 ? C1 Tb1 Tb1 132.33(16) . 7_656 ? C9 Tb1 Tb1 59.27(14) . 7_656 ? C1 O1 Tb1 91.5(5) . . ? C1 O2 Tb1 93.1(5) . . ? C9 O3 Tb1 156.1(4) . 7_656 ? C9 O3 Tb1 88.0(4) . . ? Tb1 O3 Tb1 105.97(18) 7_656 . ? C9 O4 Tb1 100.5(4) . . ? C16 O5 Tb1 134.0(4) . . ? C16 O6 Tb1 135.7(4) 7_656 . ? C17 O7 Tb1 135.0(8) . . ? C8 N1 C12 118.5(7) . 3_545 ? C19 N2 C18 122.9(13) . . ? C19 N2 C17 110.4(10) . . ? C18 N2 C17 126.4(12) . . ? O1 C1 O2 122.4(7) . . ? O1 C1 C2 120.1(8) . . ? O2 C1 C2 117.5(7) . . ? O1 C1 Tb1 62.2(4) . . ? O2 C1 Tb1 60.2(4) . . ? C2 C1 Tb1 177.7(6) . . ? C7 C2 C3 119.4(7) . . ? C7 C2 C1 120.9(8) . . ? C3 C2 C1 119.7(7) . . ? C2 C3 C4 120.4(8) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 120.8(8) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.8(7) . . ? C4 C5 C8 123.3(8) . . ? C6 C5 C8 116.9(8) . . ? C5 C6 C7 118.8(8) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C2 C7 C6 120.7(9) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? N1 C8 C5 120.0(8) . . ? N1 C8 H16 132(9) . . ? C5 C8 H16 105(9) . . ? O4 C9 O3 120.2(6) . . ? O4 C9 C10 120.2(6) . . ? O3 C9 C10 119.7(6) . . ? O4 C9 Tb1 54.4(3) . . ? O3 C9 Tb1 65.9(3) . . ? C10 C9 Tb1 173.7(5) . . ? C15 C10 C11 119.6(6) . . ? C15 C10 C9 118.8(6) . . ? C11 C10 C9 121.6(6) . . ? C12 C11 C10 121.2(6) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 119.5(6) . . ? C11 C12 N1 117.0(6) . 3_455 ? C13 C12 N1 123.6(6) . 3_455 ? C12 C13 C14 120.1(6) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 119.9(6) . . ? C15 C14 C16 119.8(6) . 4_655 ? C13 C14 C16 120.3(6) . 4_655 ? C14 C15 C10 119.7(6) . . ? C14 C15 H15 120.2 . . ? C10 C15 H15 120.2 . . ? O5 C16 O6 126.2(6) . 7_656 ? O5 C16 C14 117.6(6) . 4_645 ? O6 C16 C14 116.2(6) 7_656 4_645 ? O7 C17 N2 113.7(11) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.120 _refine_diff_density_min -1.042 _refine_diff_density_rms 0.133 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.367 -0.036 0.302 1756 434 ' ' data_UCY-11 _database_code_depnum_ccdc_archive 'CCDC 916230' #TrackingRef 'UCY-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 Dy N2 O8' _chemical_formula_sum 'C19 H14 Dy N2 O8' _chemical_formula_weight 560.82 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' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.7897(8) _cell_length_b 13.9077(7) _cell_length_c 13.6093(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.074(3) _cell_angle_gamma 90.00 _cell_volume 5380.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4531 _cell_measurement_theta_min 3.0254 _cell_measurement_theta_max 25.0485 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 2.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.69712 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12896 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4727 _reflns_number_gt 3576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.1355P)^2^+138.6045P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4727 _refine_ls_number_parameters 271 _refine_ls_number_restraints 239 _refine_ls_R_factor_all 0.0990 _refine_ls_R_factor_gt 0.0855 _refine_ls_wR_factor_ref 0.2738 _refine_ls_wR_factor_gt 0.2660 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.114 _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 Dy1 Dy 0.316076(19) 0.20925(5) 0.54109(5) 0.0513(3) Uani 1 1 d U . . O1 O 0.3878(4) 0.1744(12) 0.4794(12) 0.099(4) Uani 1 1 d U . . O2 O 0.3775(4) 0.3252(11) 0.5067(10) 0.087(4) Uani 1 1 d U . . O3 O 0.2921(3) 0.0660(8) 0.4480(9) 0.070(3) Uani 1 1 d U . . O4 O 0.2701(3) 0.3454(8) 0.5405(7) 0.060(3) Uani 1 1 d U . . O5 O 0.2697(4) 0.1658(9) 0.6616(8) 0.072(3) Uani 1 1 d U . . O6 O 0.3003(3) 0.2571(9) 0.3754(7) 0.060(3) Uani 1 1 d U . . O7 O 0.3559(5) 0.0798(14) 0.6379(11) 0.120(6) Uani 1 1 d U . . O8 O 0.3547(7) 0.2777(13) 0.6886(16) 0.126(5) Uani 1 1 d DU . . N1 N 0.5978(4) 0.4128(12) 0.3508(10) 0.073(4) Uani 1 1 d U . . N2 N 0.3805(12) 0.373(2) 0.828(2) 0.176(7) Uani 1 1 d DU . . C1 C 0.4035(7) 0.2529(19) 0.4765(14) 0.091(7) Uani 1 1 d U . . C2 C 0.4471(7) 0.2781(14) 0.4405(15) 0.079(5) Uani 1 1 d U . . C3 C 0.4629(6) 0.3701(17) 0.4400(15) 0.092(6) Uani 1 1 d U . . H3 H 0.4461 0.4194 0.4646 0.110 Uiso 1 1 calc R . . C4 C 0.5057(6) 0.3917(16) 0.4015(16) 0.089(6) Uani 1 1 d U . . H4 H 0.5152 0.4549 0.3941 0.107 Uiso 1 1 calc R . . C5 C 0.5317(7) 0.3158(18) 0.3761(15) 0.087(5) Uani 1 1 d U . . C6 C 0.5171(10) 0.2262(19) 0.373(2) 0.116(7) Uani 1 1 d U . . H6 H 0.5354 0.1772 0.3524 0.139 Uiso 1 1 calc R . . C7 C 0.4709(10) 0.2054(18) 0.403(2) 0.111(6) Uani 1 1 d U . . H7 H 0.4582 0.1437 0.3959 0.133 Uiso 1 1 calc R . . C8 C 0.5789(7) 0.331(2) 0.3498(16) 0.093(6) Uani 1 1 d U . . C9 C 0.2484(5) 0.0784(11) 0.4322(11) 0.056(4) Uani 1 1 d U . . C10 C 0.2192(5) 0.0051(12) 0.3725(11) 0.059(4) Uani 1 1 d U . . C11 C 0.2375(4) -0.0544(10) 0.3050(10) 0.051(3) Uani 1 1 d U . . H11 H 0.2689 -0.0488 0.2973 0.061 Uiso 1 1 calc R . . C12 C 0.2091(5) -0.1213(13) 0.2499(11) 0.064(4) Uani 1 1 d U . . C13 C 0.1621(5) -0.1314(13) 0.2634(13) 0.071(5) Uani 1 1 d U . . H13 H 0.1431 -0.1762 0.2257 0.085 Uiso 1 1 calc R . . C14 C 0.1442(5) -0.0777(14) 0.3296(12) 0.068(4) Uani 1 1 d U . . C15 C 0.1709(5) -0.0047(12) 0.3835(12) 0.065(4) Uani 1 1 d U . . H15 H 0.1575 0.0361 0.4252 0.078 Uiso 1 1 calc R . . C16 C 0.2280(5) 0.1825(12) 0.6710(11) 0.059(4) Uani 1 1 d U . . C17 C 0.3445(15) 0.313(3) 0.762(3) 0.179(8) Uani 1 1 d DU . . C18 C 0.3568(14) 0.419(3) 0.897(3) 0.188(9) Uani 1 1 d DU . . H18A H 0.3786 0.4568 0.9415 0.282 Uiso 1 1 calc R . . H18B H 0.3428 0.3713 0.9346 0.282 Uiso 1 1 calc R . . H18C H 0.3327 0.4594 0.8625 0.282 Uiso 1 1 calc R . . C19 C 0.4290(14) 0.373(3) 0.807(3) 0.196(9) Uani 1 1 d DU . . H19A H 0.4494 0.4028 0.8607 0.295 Uiso 1 1 calc R . . H19B H 0.4302 0.4081 0.7464 0.295 Uiso 1 1 calc R . . H19C H 0.4391 0.3079 0.7989 0.295 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Dy1 0.0247(4) 0.0784(6) 0.0540(5) 0.0003(3) 0.0156(3) -0.0023(3) O1 0.045(7) 0.132(12) 0.132(12) 0.012(10) 0.051(7) 0.011(7) O2 0.050(7) 0.119(10) 0.103(10) -0.018(8) 0.045(7) -0.009(7) O3 0.042(6) 0.067(7) 0.105(8) -0.004(6) 0.023(5) -0.004(5) O4 0.043(5) 0.085(7) 0.059(6) -0.006(5) 0.027(4) -0.011(5) O5 0.043(6) 0.106(8) 0.073(7) 0.020(7) 0.025(5) 0.003(6) O6 0.032(5) 0.098(7) 0.055(5) 0.010(6) 0.022(4) 0.019(5) O7 0.060(8) 0.200(16) 0.110(10) 0.059(11) 0.046(7) 0.059(10) O8 0.122(7) 0.127(7) 0.127(6) 0.009(4) 0.015(5) -0.005(5) N1 0.039(7) 0.111(11) 0.075(8) -0.011(8) 0.027(6) -0.017(7) N2 0.180(8) 0.175(8) 0.172(8) -0.006(5) 0.023(5) -0.002(5) C1 0.067(12) 0.130(17) 0.071(11) 0.044(12) -0.006(9) -0.048(13) C2 0.058(10) 0.096(12) 0.090(13) 0.013(10) 0.033(9) -0.022(8) C3 0.051(9) 0.125(16) 0.111(14) -0.042(13) 0.048(10) -0.009(10) C4 0.053(10) 0.096(14) 0.118(16) -0.003(12) 0.012(10) 0.001(9) C5 0.062(10) 0.127(12) 0.078(11) -0.029(11) 0.032(9) -0.008(10) C6 0.109(8) 0.118(9) 0.127(10) -0.007(7) 0.042(7) 0.007(6) C7 0.102(8) 0.109(9) 0.124(10) 0.002(7) 0.028(7) -0.001(6) C8 0.061(11) 0.135(18) 0.089(13) 0.005(13) 0.032(10) 0.006(12) C9 0.039(7) 0.069(9) 0.067(9) -0.006(7) 0.025(6) -0.009(7) C10 0.032(7) 0.079(10) 0.069(9) -0.002(8) 0.024(6) -0.006(7) C11 0.031(6) 0.072(9) 0.052(7) 0.001(7) 0.018(5) -0.002(6) C12 0.042(7) 0.090(11) 0.068(9) -0.025(8) 0.031(7) -0.011(8) C13 0.046(8) 0.089(11) 0.088(11) -0.017(9) 0.041(8) -0.021(8) C14 0.032(7) 0.107(13) 0.067(9) -0.013(9) 0.017(6) -0.008(8) C15 0.036(7) 0.080(10) 0.086(10) -0.015(9) 0.033(7) -0.009(7) C16 0.039(8) 0.089(11) 0.055(8) 0.012(8) 0.025(6) 0.002(7) C17 0.181(9) 0.181(9) 0.177(8) -0.004(5) 0.032(5) 0.001(5) C18 0.189(10) 0.187(10) 0.187(9) -0.003(5) 0.030(5) 0.001(5) C19 0.193(9) 0.199(10) 0.198(10) -0.002(5) 0.032(5) -0.002(5) _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 Dy1 O4 2.310(11) . ? Dy1 O6 2.326(10) . ? Dy1 O8 2.34(2) . ? Dy1 O5 2.350(10) . ? Dy1 O1 2.397(11) . ? Dy1 O3 2.403(11) . ? Dy1 O7 2.412(14) . ? Dy1 O2 2.492(13) . ? Dy1 O4 2.664(10) 7_556 ? Dy1 C1 2.86(2) . ? Dy1 C9 2.896(15) . ? Dy1 Dy1 3.9583(12) 7_556 ? O1 C1 1.18(3) . ? O2 C1 1.35(3) . ? O3 C9 1.253(17) . ? O4 C9 1.268(18) 7_556 ? O4 Dy1 2.665(10) 7_556 ? O5 C16 1.250(17) . ? O6 C16 1.266(18) 7_556 ? O8 C17 1.20(3) . ? N1 C8 1.27(3) . ? N1 C14 1.415(18) 3 ? N2 C18 1.40(3) . ? N2 C19 1.47(3) . ? N2 C17 1.51(3) . ? C1 C2 1.46(3) . ? C2 C3 1.36(3) . ? C2 C7 1.37(3) . ? C3 C4 1.44(2) . ? C3 H3 0.9300 . ? C4 C5 1.37(3) . ? C4 H4 0.9300 . ? C5 C6 1.31(3) . ? C5 C8 1.48(3) . ? C6 C7 1.48(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 O4 1.268(18) 7_556 ? C9 C10 1.48(2) . ? C10 C11 1.40(2) . ? C10 C15 1.427(18) . ? C11 C12 1.38(2) . ? C11 H11 0.9300 . ? C12 C13 1.400(19) . ? C12 C16 1.536(19) 6 ? C13 C14 1.33(2) . ? C13 H13 0.9300 . ? C14 C15 1.41(2) . ? C14 N1 1.415(18) 3_445 ? C15 H15 0.9300 . ? C16 O6 1.266(18) 7_556 ? C16 C12 1.536(19) 6_556 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O4 Dy1 O6 74.8(3) . . ? O4 Dy1 O8 82.2(5) . . ? O6 Dy1 O8 135.2(6) . . ? O4 Dy1 O5 79.9(4) . . ? O6 Dy1 O5 134.8(3) . . ? O8 Dy1 O5 75.6(6) . . ? O4 Dy1 O1 133.5(5) . . ? O6 Dy1 O1 76.4(4) . . ? O8 Dy1 O1 93.7(7) . . ? O5 Dy1 O1 143.8(5) . . ? O4 Dy1 O3 124.1(4) . . ? O6 Dy1 O3 74.4(4) . . ? O8 Dy1 O3 148.0(5) . . ? O5 Dy1 O3 90.4(4) . . ? O1 Dy1 O3 80.8(5) . . ? O4 Dy1 O7 146.8(4) . . ? O6 Dy1 O7 138.3(5) . . ? O8 Dy1 O7 73.4(6) . . ? O5 Dy1 O7 72.6(4) . . ? O1 Dy1 O7 71.3(5) . . ? O3 Dy1 O7 75.0(6) . . ? O4 Dy1 O2 83.8(4) . . ? O6 Dy1 O2 70.7(4) . . ? O8 Dy1 O2 69.0(6) . . ? O5 Dy1 O2 142.7(4) . . ? O1 Dy1 O2 52.3(5) . . ? O3 Dy1 O2 126.2(4) . . ? O7 Dy1 O2 107.1(5) . . ? O4 Dy1 O4 74.8(4) . 7_556 ? O6 Dy1 O4 69.6(3) . 7_556 ? O8 Dy1 O4 139.4(6) . 7_556 ? O5 Dy1 O4 67.9(3) . 7_556 ? O1 Dy1 O4 126.4(5) . 7_556 ? O3 Dy1 O4 51.1(3) . 7_556 ? O7 Dy1 O4 110.2(5) . 7_556 ? O2 Dy1 O4 138.5(4) . 7_556 ? O4 Dy1 C1 110.9(6) . . ? O6 Dy1 C1 71.8(4) . . ? O8 Dy1 C1 81.7(7) . . ? O5 Dy1 C1 153.3(4) . . ? O1 Dy1 C1 24.1(7) . . ? O3 Dy1 C1 102.0(6) . . ? O7 Dy1 C1 87.7(5) . . ? O2 Dy1 C1 28.3(6) . . ? O4 Dy1 C1 137.7(4) 7_556 . ? O4 Dy1 C9 100.1(4) . . ? O6 Dy1 C9 70.8(4) . . ? O8 Dy1 C9 152.3(6) . . ? O5 Dy1 C9 77.6(4) . . ? O1 Dy1 C9 103.9(5) . . ? O3 Dy1 C9 25.2(4) . . ? O7 Dy1 C9 92.0(6) . . ? O2 Dy1 C9 138.6(4) . . ? O4 Dy1 C9 25.9(4) 7_556 . ? C1 Dy1 C9 121.9(6) . . ? O4 Dy1 Dy1 40.5(2) . 7_556 ? O6 Dy1 Dy1 67.2(2) . 7_556 ? O8 Dy1 Dy1 115.6(5) . 7_556 ? O5 Dy1 Dy1 69.2(3) . 7_556 ? O1 Dy1 Dy1 143.2(4) . 7_556 ? O3 Dy1 Dy1 84.6(2) . 7_556 ? O7 Dy1 Dy1 136.2(3) . 7_556 ? O2 Dy1 Dy1 116.2(4) . 7_556 ? O4 Dy1 Dy1 34.3(2) 7_556 7_556 ? C1 Dy1 Dy1 134.9(4) . 7_556 ? C9 Dy1 Dy1 59.8(3) . 7_556 ? C1 O1 Dy1 100.3(16) . . ? C1 O2 Dy1 91.1(11) . . ? C9 O3 Dy1 100.0(9) . . ? C9 O4 Dy1 162.1(10) 7_556 . ? C9 O4 Dy1 87.3(8) 7_556 7_556 ? Dy1 O4 Dy1 105.2(4) . 7_556 ? C16 O5 Dy1 133.2(10) . . ? C16 O6 Dy1 133.2(9) 7_556 . ? C17 O8 Dy1 138(3) . . ? C8 N1 C14 120.0(16) . 3 ? C18 N2 C19 135(4) . . ? C18 N2 C17 107(3) . . ? C19 N2 C17 118(3) . . ? O1 C1 O2 116.3(18) . . ? O1 C1 C2 126(3) . . ? O2 C1 C2 117.9(19) . . ? O1 C1 Dy1 55.6(11) . . ? O2 C1 Dy1 60.7(9) . . ? C2 C1 Dy1 177.6(15) . . ? C3 C2 C7 120.5(18) . . ? C3 C2 C1 122(2) . . ? C7 C2 C1 117(2) . . ? C2 C3 C4 120.2(18) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 118(2) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? C6 C5 C4 124(2) . . ? C6 C5 C8 115(2) . . ? C4 C5 C8 121(2) . . ? C5 C6 C7 118(2) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C2 C7 C6 119(2) . . ? C2 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? N1 C8 C5 122(2) . . ? O3 C9 O4 121.5(14) . 7_556 ? O3 C9 C10 117.9(13) . . ? O4 C9 C10 120.4(13) 7_556 . ? O3 C9 Dy1 54.8(8) . . ? O4 C9 Dy1 66.8(7) 7_556 . ? C10 C9 Dy1 172.5(10) . . ? C11 C10 C15 119.1(14) . . ? C11 C10 C9 121.7(12) . . ? C15 C10 C9 119.2(13) . . ? C12 C11 C10 120.2(12) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.8(13) . . ? C11 C12 C16 120.6(12) . 6 ? C13 C12 C16 119.6(14) . 6 ? C14 C13 C12 121.2(15) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 121.1(13) . . ? C13 C14 N1 124.3(15) . 3_445 ? C15 C14 N1 114.6(14) . 3_445 ? C14 C15 C10 118.4(14) . . ? C14 C15 H15 120.8 . . ? C10 C15 H15 120.8 . . ? O5 C16 O6 128.7(14) . 7_556 ? O5 C16 C12 114.9(14) . 6_556 ? O6 C16 C12 116.4(12) 7_556 6_556 ? O8 C17 N2 119(4) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.817 _refine_diff_density_min -2.848 _refine_diff_density_rms 0.213 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.001 0.488 -0.013 1914 516 ' ' # start Validation Reply Form _vrf_CHEMW03_UCY-11 ; RESPONSE: The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ; _vrf_PLAT043_UCY-11 ; RESPONSE:The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ; _vrf_PLAT041_UCY-11 ; RESPONSE:The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ; _vrf_FORMU01_UCY-11 ; RESPONSE:The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ; _vrf_CELLZ01_UCY-11 ; RESPONSE:The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ; data_UCY-12 _database_code_depnum_ccdc_archive 'CCDC 916231' #TrackingRef 'UCY-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C82 H68 Ho4 N10 O31, 4 (O0.25)' _chemical_formula_sum 'C82 H68 Ho4 N10 O32' _chemical_formula_weight 2365.18 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' Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.6752(16) _cell_length_b 14.3540(7) _cell_length_c 13.3467(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.650(6) _cell_angle_gamma 90.00 _cell_volume 5415.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6104 _cell_measurement_theta_min 3.0285 _cell_measurement_theta_max 25.0735 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2308 _exptl_absorpt_coefficient_mu 2.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.59466 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18439 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4749 _reflns_number_gt 4093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0703P)^2^+571.5667P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4749 _refine_ls_number_parameters 325 _refine_ls_number_restraints 80 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0864 _refine_ls_wR_factor_ref 0.2318 _refine_ls_wR_factor_gt 0.2292 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.024 _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 Ho1 Ho 0.31659(2) 0.21251(4) 1.03973(5) 0.0298(3) Uani 1 1 d . . . O1 O 0.3892(4) 0.1833(9) 0.9816(12) 0.061(4) Uani 1 1 d . . . O2 O 0.3772(4) 0.3308(9) 1.0060(11) 0.057(3) Uani 1 1 d . . . O3 O 0.2937(4) 0.0743(7) 0.9456(9) 0.043(3) Uani 1 1 d . . . O4 O 0.2700(4) 0.3427(7) 1.0447(8) 0.039(2) Uani 1 1 d . . . O5 O 0.2993(3) 0.2623(7) 0.8721(9) 0.040(3) Uani 1 1 d . . . O6 O 0.2288(4) 0.3361(8) 0.8391(9) 0.046(3) Uani 1 1 d . . . O7 O 0.3589(8) 0.2729(16) 1.1880(17) 0.060(7) Uani 0.75 1 d PDU . . O7A O 0.3460(15) 0.288(3) 1.200(3) 0.014(8) Uani 0.25 1 d PU . . O8 O 0.3575(5) 0.0891(11) 1.1373(11) 0.043(3) Uani 0.75 1 d PDU . . O8A O 0.350(2) 0.025(5) 1.142(5) 0.078(17) Uani 0.25 1 d PU . . N1 N 0.4023(4) 0.4211(11) 0.6498(12) 0.049(4) Uani 1 1 d . . . N2 N 0.3771(13) 0.370(3) 1.330(3) 0.119(11) Uani 0.75 1 d PDU . . N3 N 0.3821(11) 0.013(2) 1.304(2) 0.095(9) Uani 0.75 1 d PDU . . C1 C 0.4025(6) 0.2636(14) 0.9800(13) 0.047(4) Uani 1 1 d . . . C2 C 0.4472(6) 0.2873(12) 0.9430(15) 0.048(4) Uani 1 1 d . . . C3 C 0.4611(7) 0.3762(15) 0.9341(17) 0.063(6) Uani 1 1 d . . . H3 H 0.4421 0.4247 0.9500 0.076 Uiso 1 1 calc R . . C4 C 0.5051(6) 0.3967(14) 0.9000(16) 0.057(5) Uani 1 1 d . . . H4 H 0.5148 0.4580 0.8938 0.069 Uiso 1 1 calc R . . C5 C 0.4675(7) 0.3232(16) 0.6231(18) 0.068(6) Uani 1 1 d . . . C6 C 0.5195(10) 0.236(2) 0.888(4) 0.16(2) Uani 1 1 d . . . H6 H 0.5404 0.1875 0.8808 0.194 Uiso 1 1 calc R . . C7 C 0.4745(8) 0.2151(17) 0.910(3) 0.107(12) Uani 1 1 d . . . H7 H 0.4628 0.1546 0.9033 0.128 Uiso 1 1 calc R . . C8 C 0.4194(6) 0.3415(15) 0.6489(15) 0.058(5) Uani 1 1 d . . . C9 C 0.2490(5) 0.0855(11) 0.9264(11) 0.035(3) Uani 1 1 d . . . C10 C 0.2198(5) 0.0107(10) 0.8701(12) 0.035(3) Uani 1 1 d . . . C11 C 0.2614(5) 0.4509(10) 0.6956(12) 0.035(3) Uani 1 1 d . . . H11 H 0.2299 0.4564 0.7033 0.041 Uiso 1 1 calc R . . C12 C 0.2901(5) 0.3831(10) 0.7498(11) 0.034(3) Uani 1 1 d . . . C13 C 0.3370(5) 0.3732(11) 0.7362(12) 0.040(4) Uani 1 1 d . . . H13 H 0.3561 0.3285 0.7730 0.048 Uiso 1 1 calc R . . C14 C 0.3551(5) 0.4296(11) 0.6681(12) 0.040(4) Uani 1 1 d . . . C15 C 0.3279(5) 0.5015(10) 0.6186(12) 0.038(4) Uani 1 1 d . . . H15 H 0.3412 0.5433 0.5782 0.046 Uiso 1 1 calc R . . C16 C 0.2712(5) 0.3222(12) 0.8273(13) 0.041(4) Uani 1 1 d . . . C17 C 0.3442(16) 0.317(3) 1.253(3) 0.124(16) Uani 0.75 1 d PDU . . C18 C 0.3548(16) 0.418(3) 1.393(3) 0.118(14) Uani 0.75 1 d PDU . . H18A H 0.3237 0.3930 1.3911 0.177 Uiso 0.75 1 calc PR . . H18B H 0.3524 0.4823 1.3715 0.177 Uiso 0.75 1 calc PR . . H18C H 0.3723 0.4144 1.4605 0.177 Uiso 0.75 1 calc PR . . C19 C 0.4222(14) 0.378(3) 1.305(3) 0.123(15) Uani 0.75 1 d PDU . . H19A H 0.4267 0.3311 1.2571 0.184 Uiso 0.75 1 calc PR . . H19B H 0.4453 0.3710 1.3657 0.184 Uiso 0.75 1 calc PR . . H19C H 0.4256 0.4387 1.2765 0.184 Uiso 0.75 1 calc PR . . C20 C 0.3658(13) 0.087(3) 1.233(2) 0.094(11) Uani 0.75 1 d PDU . . C21 C 0.372(2) -0.070(4) 1.236(4) 0.18(2) Uani 0.75 1 d PDU . . H21A H 0.3816 -0.1258 1.2744 0.265 Uiso 0.75 1 calc PR . . H21B H 0.3901 -0.0654 1.1813 0.265 Uiso 0.75 1 calc PR . . H21C H 0.3392 -0.0731 1.2089 0.265 Uiso 0.75 1 calc PR . . C22 C 0.402(2) 0.026(4) 1.411(4) 0.18(2) Uani 0.75 1 d PDU . . H22A H 0.4100 -0.0331 1.4418 0.263 Uiso 0.75 1 calc PR . . H22B H 0.3798 0.0576 1.4445 0.263 Uiso 0.75 1 calc PR . . H22C H 0.4305 0.0634 1.4155 0.263 Uiso 0.75 1 calc PR . . 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 Ho1 0.0197(3) 0.0308(4) 0.0416(4) -0.0001(3) 0.0126(3) -0.0014(3) O1 0.036(6) 0.054(8) 0.103(11) 0.009(7) 0.037(7) 0.005(6) O2 0.045(7) 0.051(7) 0.084(9) -0.022(7) 0.036(7) -0.015(6) O3 0.035(6) 0.029(5) 0.069(8) -0.005(5) 0.019(5) -0.003(4) O4 0.033(5) 0.034(6) 0.054(7) -0.009(5) 0.021(5) -0.004(4) O5 0.028(5) 0.042(6) 0.055(7) 0.011(5) 0.022(5) 0.016(5) O6 0.031(6) 0.056(7) 0.057(7) 0.022(6) 0.025(5) 0.005(5) O7 0.058(8) 0.062(8) 0.058(8) -0.003(5) 0.009(5) 0.001(5) O7A 0.015(9) 0.014(9) 0.014(9) -0.002(5) 0.001(5) 0.000(5) O8 0.039(5) 0.046(5) 0.044(5) 0.005(4) 0.010(4) 0.006(4) O8A 0.077(18) 0.079(18) 0.078(18) -0.001(5) 0.015(6) 0.000(5) N1 0.025(7) 0.061(10) 0.068(10) 0.015(8) 0.026(7) 0.008(6) N2 0.120(12) 0.119(12) 0.118(12) -0.001(5) 0.018(5) -0.001(5) N3 0.095(10) 0.093(10) 0.095(10) 0.002(5) 0.014(5) 0.000(5) C1 0.031(8) 0.065(12) 0.047(10) 0.003(9) 0.010(7) -0.008(8) C2 0.034(8) 0.045(10) 0.070(12) -0.003(9) 0.018(8) -0.009(7) C3 0.047(10) 0.063(12) 0.090(15) -0.016(11) 0.040(11) -0.004(9) C4 0.044(10) 0.050(11) 0.078(13) -0.014(10) 0.010(9) -0.004(8) C5 0.050(11) 0.068(13) 0.096(16) 0.026(12) 0.039(11) 0.012(10) C6 0.073(17) 0.09(2) 0.34(6) -0.13(3) 0.12(3) -0.042(16) C7 0.043(12) 0.061(14) 0.23(4) 0.029(18) 0.053(17) -0.005(10) C8 0.042(10) 0.079(14) 0.059(11) 0.008(10) 0.026(9) 0.009(10) C9 0.028(7) 0.038(8) 0.043(8) 0.001(7) 0.020(6) 0.000(6) C10 0.027(7) 0.029(7) 0.053(9) 0.005(7) 0.018(7) 0.000(6) C11 0.024(7) 0.035(8) 0.047(9) 0.002(7) 0.013(6) 0.003(6) C12 0.030(7) 0.038(8) 0.039(8) 0.005(7) 0.017(6) 0.002(6) C13 0.034(8) 0.039(8) 0.052(9) 0.017(7) 0.023(7) 0.011(7) C14 0.029(8) 0.044(9) 0.050(9) 0.001(7) 0.019(7) 0.006(7) C15 0.038(8) 0.030(8) 0.055(10) 0.013(7) 0.030(7) 0.005(6) C16 0.026(8) 0.048(9) 0.048(9) 0.015(8) 0.007(7) 0.003(7) C17 0.124(16) 0.124(16) 0.123(16) 0.001(5) 0.021(6) 0.000(5) C18 0.119(15) 0.118(15) 0.117(15) 0.001(5) 0.019(5) 0.000(5) C19 0.123(15) 0.122(15) 0.122(15) 0.000(5) 0.020(6) 0.001(5) C20 0.093(11) 0.094(11) 0.095(11) 0.000(5) 0.014(5) 0.000(5) C21 0.18(2) 0.18(2) 0.18(2) -0.002(5) 0.031(6) 0.000(5) C22 0.18(2) 0.18(2) 0.18(2) -0.001(5) 0.030(6) 0.000(5) _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 Ho1 O4 2.304(10) . ? Ho1 O7 2.31(2) . ? Ho1 O5 2.322(11) . ? Ho1 O6 2.345(10) 7_557 ? Ho1 O1 2.377(11) . ? Ho1 O3 2.380(11) . ? Ho1 O8 2.387(15) . ? Ho1 O7A 2.42(4) . ? Ho1 O2 2.523(11) . ? Ho1 O4 2.670(10) 7_557 ? Ho1 C1 2.812(16) . ? Ho1 C9 2.895(15) . ? O1 C1 1.22(2) . ? O2 C1 1.29(2) . ? O3 C9 1.275(17) . ? O4 C9 1.257(17) 7_557 ? O4 Ho1 2.670(10) 7_557 ? O5 C16 1.259(18) . ? O6 C16 1.268(18) . ? O6 Ho1 2.345(10) 7_557 ? O7 C17 1.20(4) . ? O7A C17 0.83(5) . ? O8 O8A 0.95(7) . ? O8 C20 1.26(3) . ? O8A C20 1.51(7) . ? O8A C21 1.90(9) . ? N1 C8 1.24(2) . ? N1 C14 1.422(18) . ? N2 C18 1.33(4) . ? N2 C19 1.39(4) . ? N2 C17 1.49(4) . ? N3 C20 1.44(3) . ? N3 C22 1.46(4) . ? N3 C21 1.50(4) . ? C1 C2 1.49(2) . ? C2 C3 1.35(3) . ? C2 C7 1.41(3) . ? C3 C4 1.44(2) . ? C3 H3 0.9300 . ? C4 C5 1.38(3) 2_656 ? C4 H4 0.9300 . ? C5 C6 1.33(4) 2_656 ? C5 C4 1.38(3) 2_656 ? C5 C8 1.50(2) . ? C6 C5 1.33(4) 2_656 ? C6 C7 1.40(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 O4 1.257(17) 7_557 ? C9 C10 1.49(2) . ? C10 C11 1.40(2) 4_546 ? C10 C15 1.409(19) 4_546 ? C11 C12 1.39(2) . ? C11 C10 1.40(2) 4_556 ? C11 H11 0.9300 . ? C12 C13 1.39(2) . ? C12 C16 1.52(2) . ? C13 C14 1.38(2) . ? C13 H13 0.9300 . ? C14 C15 1.39(2) . ? C15 C10 1.409(19) 4_556 ? C15 H15 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O4 Ho1 O7 84.0(6) . . ? O4 Ho1 O5 75.4(4) . . ? O7 Ho1 O5 135.0(6) . . ? O4 Ho1 O6 80.2(4) . 7_557 ? O7 Ho1 O6 78.1(7) . 7_557 ? O5 Ho1 O6 134.7(4) . 7_557 ? O4 Ho1 O1 134.1(4) . . ? O7 Ho1 O1 89.0(7) . . ? O5 Ho1 O1 78.3(4) . . ? O6 Ho1 O1 142.1(4) 7_557 . ? O4 Ho1 O3 125.6(4) . . ? O7 Ho1 O3 145.4(6) . . ? O5 Ho1 O3 75.7(4) . . ? O6 Ho1 O3 88.9(4) 7_557 . ? O1 Ho1 O3 81.9(4) . . ? O4 Ho1 O8 145.1(4) . . ? O7 Ho1 O8 70.8(7) . . ? O5 Ho1 O8 139.5(4) . . ? O6 Ho1 O8 71.4(4) 7_557 . ? O1 Ho1 O8 70.8(5) . . ? O3 Ho1 O8 74.7(5) . . ? O4 Ho1 O7A 74.2(10) . . ? O7 Ho1 O7A 11.4(10) . . ? O5 Ho1 O7A 134.3(10) . . ? O6 Ho1 O7A 71.1(10) 7_557 . ? O1 Ho1 O7A 100.0(11) . . ? O3 Ho1 O7A 149.9(10) . . ? O8 Ho1 O7A 77.6(10) . . ? O4 Ho1 O2 83.0(4) . . ? O7 Ho1 O2 67.8(6) . . ? O5 Ho1 O2 70.3(4) . . ? O6 Ho1 O2 143.3(4) 7_557 . ? O1 Ho1 O2 52.7(4) . . ? O3 Ho1 O2 127.1(4) . . ? O8 Ho1 O2 107.9(5) . . ? O7A Ho1 O2 72.9(10) . . ? O4 Ho1 O4 75.6(4) . 7_557 ? O7 Ho1 O4 142.3(6) . 7_557 ? O5 Ho1 O4 69.6(4) . 7_557 ? O6 Ho1 O4 67.6(4) 7_557 7_557 ? O1 Ho1 O4 127.8(4) . 7_557 ? O3 Ho1 O4 51.4(3) . 7_557 ? O8 Ho1 O4 110.3(5) . 7_557 ? O7A Ho1 O4 131.9(11) . 7_557 ? O2 Ho1 O4 138.1(4) . 7_557 ? O4 Ho1 C1 109.6(5) . . ? O7 Ho1 C1 77.6(7) . . ? O5 Ho1 C1 72.6(4) . . ? O6 Ho1 C1 152.5(5) 7_557 . ? O1 Ho1 C1 25.4(5) . . ? O3 Ho1 C1 104.2(5) . . ? O8 Ho1 C1 88.6(5) . . ? O7A Ho1 C1 86.6(11) . . ? O2 Ho1 C1 27.3(5) . . ? O4 Ho1 C1 139.0(4) 7_557 . ? O4 Ho1 C9 100.7(4) . . ? O7 Ho1 C9 153.3(6) . . ? O5 Ho1 C9 71.0(4) . . ? O6 Ho1 C9 76.9(4) 7_557 . ? O1 Ho1 C9 105.3(4) . . ? O3 Ho1 C9 25.7(4) . . ? O8 Ho1 C9 92.4(5) . . ? O7A Ho1 C9 148.0(10) . . ? O2 Ho1 C9 138.7(4) . . ? O4 Ho1 C9 25.7(3) 7_557 . ? C1 Ho1 C9 123.9(5) . . ? C1 O1 Ho1 97.7(11) . . ? C1 O2 Ho1 88.9(10) . . ? C9 O3 Ho1 100.4(9) . . ? C9 O4 Ho1 163.2(11) 7_557 . ? C9 O4 Ho1 87.2(9) 7_557 7_557 ? Ho1 O4 Ho1 104.4(4) . 7_557 ? C16 O5 Ho1 133.1(10) . . ? C16 O6 Ho1 133.8(10) . 7_557 ? C17 O7 Ho1 128(3) . . ? C17 O7A Ho1 156(5) . . ? O8A O8 C20 85(5) . . ? O8A O8 Ho1 131(4) . . ? C20 O8 Ho1 124.3(19) . . ? O8 O8A C20 56(4) . . ? O8 O8A C21 133(6) . . ? C20 O8A C21 82(4) . . ? C8 N1 C14 117.9(15) . . ? C18 N2 C19 132(4) . . ? C18 N2 C17 113(4) . . ? C19 N2 C17 113(4) . . ? C20 N3 C22 125(4) . . ? C20 N3 C21 101(3) . . ? C22 N3 C21 134(4) . . ? O1 C1 O2 120.7(15) . . ? O1 C1 C2 120.9(17) . . ? O2 C1 C2 118.3(16) . . ? O1 C1 Ho1 56.9(8) . . ? O2 C1 Ho1 63.8(8) . . ? C2 C1 Ho1 176.7(13) . . ? C3 C2 C7 118.6(16) . . ? C3 C2 C1 121.9(16) . . ? C7 C2 C1 119.3(16) . . ? C2 C3 C4 120.5(17) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 118.5(18) 2_656 . ? C5 C4 H4 120.8 2_656 . ? C3 C4 H4 120.8 . . ? C6 C5 C4 121.1(19) 2_656 2_656 ? C6 C5 C8 119(2) 2_656 . ? C4 C5 C8 119.9(19) 2_656 . ? C5 C6 C7 121(2) 2_656 . ? C5 C6 H6 119.7 2_656 . ? C7 C6 H6 119.7 . . ? C6 C7 C2 119(2) . . ? C6 C7 H7 120.4 . . ? C2 C7 H7 120.4 . . ? N1 C8 C5 122.8(18) . . ? O4 C9 O3 121.0(14) 7_557 . ? O4 C9 C10 120.7(13) 7_557 . ? O3 C9 C10 118.3(13) . . ? O4 C9 Ho1 67.1(8) 7_557 . ? O3 C9 Ho1 54.0(7) . . ? C10 C9 Ho1 172.0(10) . . ? C11 C10 C15 119.5(14) 4_546 4_546 ? C11 C10 C9 121.2(12) 4_546 . ? C15 C10 C9 119.3(13) 4_546 . ? C12 C11 C10 119.9(13) . 4_556 ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 4_556 . ? C11 C12 C13 120.0(13) . . ? C11 C12 C16 120.5(12) . . ? C13 C12 C16 119.4(13) . . ? C14 C13 C12 120.2(14) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.3(13) . . ? C13 C14 N1 122.5(14) . . ? C15 C14 N1 117.1(14) . . ? C14 C15 C10 119.7(13) . 4_556 ? C14 C15 H15 120.2 . . ? C10 C15 H15 120.2 4_556 . ? O5 C16 O6 127.0(14) . . ? O5 C16 C12 116.2(13) . . ? O6 C16 C12 116.8(13) . . ? O7A C17 O7 17(3) . . ? O7A C17 N2 137(6) . . ? O7 C17 N2 121(4) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 C20 N3 132(3) . . ? O8 C20 O8A 39(3) . . ? N3 C20 O8A 97(4) . . ? N3 C21 O8A 80(3) . . ? N3 C21 H21A 109.5 . . ? O8A C21 H21A 170.3 . . ? N3 C21 H21B 109.5 . . ? O8A C21 H21B 67.3 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? O8A C21 H21C 64.7 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.844 _refine_diff_density_min -3.485 _refine_diff_density_rms 0.256 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 -0.002 311 85 ' ' 2 0.250 0.250 0.000 156 53 ' ' 3 0.500 0.000 -0.002 311 85 ' ' 4 0.750 0.750 0.000 155 53 ' ' 5 0.250 0.750 0.500 155 53 ' ' 6 0.750 0.250 0.500 155 53 ' ' # start Validation Reply Form _vrf_CHEMW03_UCY-12 ; RESPONSE: The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ; _vrf_PLAT043_UCY-12 ; RESPONSE:The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ; _vrf_PLAT041_UCY-12 ; RESPONSE:The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ; _vrf_FORMU01_UCY-12 ; RESPONSE:The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ; _vrf_CELLZ01_UCY-12 ; RESPONSE:The reported formula, molecular weight, F000, density etc include the contribution of imine H atoms, which could not be located. ;