# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jian Zhao' _publ_contact_author_email jszhao@nwu.edu.cn _publ_section_title ; A Series of lanthanide organic polymers incorporating nitrogen-heterocyclic and aliphatic carboxylate mixed ligands: structures, luminescent and magnetic properties ; loop_ _publ_author_name 'Xun Feng.' 'Bin Liu.' 'Li Wang.' 'Jian Zhao.' 'Jian Wang.' 'Ng Weng.' 'Xin Shi.' # Attachment '- 6. Ce.cif' data_6ce _database_code_depnum_ccdc_archive 'CCDC 759404' #TrackingRef '- 6. Ce.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 Ce N2 O9' _chemical_formula_weight 434.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.748(4) _cell_length_b 13.808(6) _cell_length_c 11.660(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.424(5) _cell_angle_gamma 90.00 _cell_volume 1407.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2248 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 23.11 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.050 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 3.281 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5321 _exptl_absorpt_correction_T_max 0.7566 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10151 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2615 _reflns_number_gt 1744 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0885P)^2^+11.6455P] 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 2615 _refine_ls_number_parameters 202 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0994 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1736 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.046 _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 C6 C 0.8943(4) 0.3381(6) -0.0440(4) 0.074(2) Uani 0.733(8) 1 d PDU A 1 H6A H 0.9589 0.3046 -0.0967 0.088 Uiso 0.733(8) 1 calc PR A 1 H6B H 0.8843 0.4050 -0.0687 0.088 Uiso 0.733(8) 1 calc PR A 1 C7 C 0.7367(4) 0.2903(6) -0.0446(4) 0.079(2) Uani 0.733(8) 1 d PDU A 1 H7A H 0.7460 0.2249 -0.0147 0.094 Uiso 0.733(8) 1 calc PR A 1 H7B H 0.6700 0.3265 0.0041 0.094 Uiso 0.733(8) 1 calc PR A 1 C8 C 0.6682(7) 0.2876(8) -0.1672(4) 0.093(4) Uani 0.733(8) 1 d PDU A 1 H8A H 0.6421 0.3522 -0.1915 0.140 Uiso 0.733(8) 1 calc PR A 1 H8B H 0.5778 0.2481 -0.1698 0.140 Uiso 0.733(8) 1 calc PR A 1 H8C H 0.7416 0.2609 -0.2173 0.140 Uiso 0.733(8) 1 calc PR A 1 C6' C 0.8685(10) 0.3157(4) -0.0325(3) 0.074(2) Uani 0.267(8) 1 d PD A 2 H6'1 H 0.8966 0.2543 -0.0662 0.088 Uiso 0.267(8) 1 calc PR A 2 H6'2 H 0.7613 0.3127 -0.0146 0.088 Uiso 0.267(8) 1 calc PR A 2 C7' C 0.8939(10) 0.3979(5) -0.1174(3) 0.079(2) Uani 0.267(8) 1 d PD A 2 H7'1 H 1.0014 0.4015 -0.1343 0.094 Uiso 0.267(8) 1 calc PR A 2 H7'2 H 0.8642 0.4591 -0.0842 0.094 Uiso 0.267(8) 1 calc PR A 2 C8' C 0.7981(12) 0.3788(9) -0.2279(4) 0.093(4) Uani 0.267(8) 1 d PD A 2 H8'1 H 0.7237 0.3295 -0.2142 0.140 Uiso 0.267(8) 1 calc PR A 2 H8'2 H 0.8637 0.3577 -0.2870 0.140 Uiso 0.267(8) 1 calc PR A 2 H8'3 H 0.7467 0.4373 -0.2518 0.140 Uiso 0.267(8) 1 calc PR A 2 Ce1 Ce 1.23033(3) 0.13308(2) 0.05995(3) 0.02576(8) Uani 1 1 d . . . O1 O 1.2482(6) 0.1664(4) 0.2557(4) 0.0588(16) Uani 1 1 d . . . O2 O 1.2371(6) 0.2608(4) 0.4088(4) 0.0539(16) Uani 1 1 d . . . O3 O 1.0127(6) 0.4019(4) 0.4584(4) 0.0534(15) Uani 1 1 d . . . O4 O 0.8600(6) 0.4970(4) 0.3490(5) 0.0702(18) Uani 1 1 d . . . O5 O 1.3479(6) 0.0461(4) -0.0860(4) 0.0588(16) Uani 1 1 d . . . O6 O 1.5464(6) -0.0489(4) -0.1314(4) 0.0589(16) Uani 1 1 d . . . N1 N 1.0698(7) 0.2732(4) 0.1217(5) 0.0528(19) Uani 1 1 d . A . N2 N 0.9172(7) 0.3962(5) 0.1569(5) 0.0580(19) Uani 1 1 d . A . H2 H 0.8481 0.4399 0.1460 0.070 Uiso 1 1 calc R . . C1 C 1.0902(8) 0.3008(5) 0.2349(6) 0.046(2) Uani 1 1 d . . . C2 C 0.9977(8) 0.3774(4) 0.2593(6) 0.0438(19) Uani 1 1 d . . . C3 C 0.9664(5) 0.3339(4) 0.0772(3) 0.056(2) Uani 1 1 d D . . C4 C 1.1978(8) 0.2416(4) 0.3056(6) 0.045(2) Uani 1 1 d . . . C5 C 0.9579(8) 0.4296(5) 0.3619(6) 0.045(2) Uani 1 1 d . . . C9 C 1.4703(8) -0.0010(5) -0.0633(6) 0.051(2) Uani 1 1 d . . . O7 O 1.4396(6) 0.2431(4) 0.0917(5) 0.080(2) Uani 1 1 d . . . H1W H 1.4260 0.3005 0.1098 0.121 Uiso 1 1 d R . . H2W H 1.5263 0.2215 0.1139 0.121 Uiso 1 1 d R . . O8 O 0.3276(7) 0.0233(4) 0.4084(5) 0.082(2) Uani 1 1 d . . . H3W H 0.3071 0.0703 0.3656 0.123 Uiso 1 1 d R . . H4W H 0.3066 0.0356 0.4756 0.123 Uiso 1 1 d R . . O9 O 0.4059(9) 0.4338(5) 0.1493(6) 0.107(3) Uani 1 1 d . . . H5W H 0.3925 0.4391 0.2190 0.161 Uiso 1 1 d R . . H6W H 0.4876 0.4610 0.1324 0.161 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C6 0.079(4) 0.078(4) 0.062(4) -0.009(4) -0.015(3) 0.021(4) C7 0.079(4) 0.084(4) 0.072(4) -0.011(4) -0.020(4) 0.013(4) C8 0.088(7) 0.106(7) 0.085(6) -0.042(6) -0.019(6) 0.021(6) C6' 0.079(4) 0.078(4) 0.062(4) -0.009(4) -0.015(3) 0.021(4) C7' 0.079(4) 0.084(4) 0.072(4) -0.011(4) -0.020(4) 0.013(4) C8' 0.088(7) 0.106(7) 0.085(6) -0.042(6) -0.019(6) 0.021(6) Ce1 0.02577(14) 0.02034(14) 0.03108(15) -0.00022(14) 0.00008(11) 0.00099(15) O1 0.074(3) 0.043(3) 0.058(3) -0.005(2) -0.004(3) 0.020(3) O2 0.066(3) 0.054(3) 0.041(3) -0.003(2) -0.006(2) 0.002(3) O3 0.059(3) 0.048(3) 0.053(3) 0.000(2) -0.007(2) 0.002(2) O4 0.071(3) 0.063(3) 0.075(4) -0.017(3) -0.014(3) 0.034(3) O5 0.056(3) 0.055(3) 0.066(3) -0.011(3) 0.002(3) 0.018(3) O6 0.057(3) 0.060(3) 0.060(3) 0.001(3) 0.006(2) 0.020(3) N1 0.051(3) 0.043(3) 0.064(4) -0.001(3) 0.001(3) 0.011(3) N2 0.060(4) 0.053(3) 0.061(4) 0.002(3) 0.002(3) 0.027(3) C1 0.044(4) 0.050(4) 0.044(4) 0.002(3) -0.008(3) -0.002(3) C2 0.050(4) 0.038(3) 0.043(3) -0.003(3) -0.005(3) 0.008(3) C3 0.049(4) 0.060(4) 0.058(4) -0.011(4) -0.004(3) 0.021(4) C4 0.047(4) 0.027(3) 0.061(4) 0.002(3) 0.010(3) -0.010(3) C5 0.042(4) 0.042(4) 0.052(4) -0.003(3) -0.008(3) 0.002(3) C9 0.040(4) 0.050(4) 0.064(4) -0.006(4) 0.004(3) 0.010(3) O7 0.057(3) 0.076(4) 0.106(5) 0.014(3) -0.018(3) -0.015(3) O8 0.090(4) 0.057(3) 0.097(4) 0.019(3) -0.021(4) -0.007(3) O9 0.108(5) 0.097(5) 0.115(5) -0.004(4) -0.014(5) -0.027(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 C6 C3 1.525(5) . ? C6 C7 1.529(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.526(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C6' C7' 1.529(7) . ? C6' C3 1.530(6) . ? C6' H6'1 0.9700 . ? C6' H6'2 0.9700 . ? C7' C8' 1.530(7) . ? C7' H7'1 0.9700 . ? C7' H7'2 0.9700 . ? C8' H8'1 0.9600 . ? C8' H8'2 0.9600 . ? C8' H8'3 0.9600 . ? Ce1 O3 2.252(5) 4_565 ? Ce1 O2 2.295(5) 4_565 ? Ce1 O4 2.314(5) 2_745 ? Ce1 O1 2.326(5) . ? Ce1 O5 2.354(5) . ? Ce1 O6 2.393(5) 3_855 ? Ce1 O7 2.395(6) . ? Ce1 N1 2.514(6) . ? O1 C4 1.278(8) . ? O2 C4 1.266(8) . ? O2 Ce1 2.295(5) 4_566 ? O3 C5 1.263(8) . ? O3 Ce1 2.252(5) 4_566 ? O4 C5 1.269(9) . ? O4 Ce1 2.314(5) 2_755 ? O5 C9 1.272(9) . ? O6 C9 1.247(9) . ? O6 Ce1 2.393(5) 3_855 ? N1 C3 1.322(8) . ? N1 C1 1.378(9) . ? N2 C3 1.349(8) . ? N2 C2 1.384(9) . ? N2 H2 0.8600 . ? C1 C2 1.369(10) . ? C1 C4 1.473(9) . ? C2 C5 1.452(10) . ? C9 C9 1.545(14) 3_855 ? O7 H1W 0.8299 . ? O7 H2W 0.8458 . ? O8 H3W 0.8328 . ? O8 H4W 0.8297 . ? O9 H5W 0.8303 . ? O9 H6W 0.8385 . ? 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 C3 C6 C7 109.0(4) . . ? C3 C6 H6A 109.9 . . ? C7 C6 H6A 109.9 . . ? C3 C6 H6B 109.9 . . ? C7 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C8 C7 C6 109.4(4) . . ? C8 C7 H7A 109.8 . . ? C6 C7 H7A 109.8 . . ? C8 C7 H7B 109.8 . . ? C6 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? C7' C6' C3 109.1(5) . . ? C7' C6' H6'1 109.9 . . ? C3 C6' H6'1 109.9 . . ? C7' C6' H6'2 109.8 . . ? C3 C6' H6'2 109.8 . . ? H6'1 C6' H6'2 108.3 . . ? C6' C7' C8' 109.2(6) . . ? C6' C7' H7'1 109.8 . . ? C8' C7' H7'1 109.8 . . ? C6' C7' H7'2 109.8 . . ? C8' C7' H7'2 109.8 . . ? H7'1 C7' H7'2 108.3 . . ? C7' C8' H8'1 109.5 . . ? C7' C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? C7' C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? O3 Ce1 O2 77.39(18) 4_565 4_565 ? O3 Ce1 O4 76.67(18) 4_565 2_745 ? O2 Ce1 O4 153.06(18) 4_565 2_745 ? O3 Ce1 O1 125.35(19) 4_565 . ? O2 Ce1 O1 128.62(17) 4_565 . ? O4 Ce1 O1 73.77(19) 2_745 . ? O3 Ce1 O5 84.02(18) 4_565 . ? O2 Ce1 O5 75.19(18) 4_565 . ? O4 Ce1 O5 94.92(19) 2_745 . ? O1 Ce1 O5 142.80(18) . . ? O3 Ce1 O6 137.62(18) 4_565 3_855 ? O2 Ce1 O6 122.06(18) 4_565 3_855 ? O4 Ce1 O6 74.65(19) 2_745 3_855 ? O1 Ce1 O6 74.60(18) . 3_855 ? O5 Ce1 O6 68.22(17) . 3_855 ? O3 Ce1 O7 147.25(19) 4_565 . ? O2 Ce1 O7 70.70(19) 4_565 . ? O4 Ce1 O7 135.9(2) 2_745 . ? O1 Ce1 O7 72.8(2) . . ? O5 Ce1 O7 94.6(2) . . ? O6 Ce1 O7 69.32(19) 3_855 . ? O3 Ce1 N1 81.12(19) 4_565 . ? O2 Ce1 N1 76.17(19) 4_565 . ? O4 Ce1 N1 106.7(2) 2_745 . ? O1 Ce1 N1 65.31(19) . . ? O5 Ce1 N1 149.97(19) . . ? O6 Ce1 N1 137.06(18) 3_855 . ? O7 Ce1 N1 84.3(2) . . ? C4 O1 Ce1 126.7(4) . . ? C4 O2 Ce1 148.1(4) . 4_566 ? C5 O3 Ce1 144.5(5) . 4_566 ? C5 O4 Ce1 141.5(5) . 2_755 ? C9 O5 Ce1 120.1(5) . . ? C9 O6 Ce1 119.0(4) . 3_855 ? C3 N1 C1 105.0(5) . . ? C3 N1 Ce1 139.2(4) . . ? C1 N1 Ce1 115.8(4) . . ? C3 N2 C2 108.0(5) . . ? C3 N2 H2 126.0 . . ? C2 N2 H2 126.0 . . ? C2 C1 N1 111.0(6) . . ? C2 C1 C4 133.0(6) . . ? N1 C1 C4 115.9(6) . . ? C1 C2 N2 104.4(6) . . ? C1 C2 C5 136.0(6) . . ? N2 C2 C5 119.2(6) . . ? N1 C3 N2 111.5(5) . . ? N1 C3 C6 129.6(5) . . ? N2 C3 C6 118.8(5) . . ? N1 C3 C6' 125.0(6) . . ? N2 C3 C6' 119.8(5) . . ? C6 C3 C6' 15.4(3) . . ? O2 C4 O1 121.2(6) . . ? O2 C4 C1 123.9(6) . . ? O1 C4 C1 114.9(6) . . ? O3 C5 O4 123.8(7) . . ? O3 C5 C2 119.2(6) . . ? O4 C5 C2 116.7(6) . . ? O6 C9 O5 127.3(7) . . ? O6 C9 C9 116.8(8) . 3_855 ? O5 C9 C9 115.8(8) . 3_855 ? Ce1 O7 H1W 121.9 . . ? Ce1 O7 H2W 119.6 . . ? H1W O7 H2W 113.3 . . ? H3W O8 H4W 110.9 . . ? H5W O9 H6W 110.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C6 C7 C8 -176.0(7) . . . . ? C3 C6' C7' C8' 179.1(7) . . . . ? O3 Ce1 O1 C4 -69.2(6) 4_565 . . . ? O2 Ce1 O1 C4 33.7(7) 4_565 . . . ? O4 Ce1 O1 C4 -129.2(6) 2_745 . . . ? O5 Ce1 O1 C4 154.5(5) . . . . ? O6 Ce1 O1 C4 152.7(6) 3_855 . . . ? O7 Ce1 O1 C4 80.0(6) . . . . ? N1 Ce1 O1 C4 -11.5(5) . . . . ? O3 Ce1 O5 C9 -149.0(5) 4_565 . . . ? O2 Ce1 O5 C9 132.5(6) 4_565 . . . ? O4 Ce1 O5 C9 -73.0(5) 2_745 . . . ? O1 Ce1 O5 C9 -3.5(7) . . . . ? O6 Ce1 O5 C9 -1.7(5) 3_855 . . . ? O7 Ce1 O5 C9 63.9(5) . . . . ? N1 Ce1 O5 C9 150.5(5) . . . . ? O3 Ce1 N1 C3 -38.9(7) 4_565 . . . ? O2 Ce1 N1 C3 40.2(7) 4_565 . . . ? O4 Ce1 N1 C3 -112.0(7) 2_745 . . . ? O1 Ce1 N1 C3 -174.7(7) . . . . ? O5 Ce1 N1 C3 22.3(9) . . . . ? O6 Ce1 N1 C3 162.7(6) 3_855 . . . ? O7 Ce1 N1 C3 111.7(7) . . . . ? O3 Ce1 N1 C1 142.2(5) 4_565 . . . ? O2 Ce1 N1 C1 -138.7(5) 4_565 . . . ? O4 Ce1 N1 C1 69.1(5) 2_745 . . . ? O1 Ce1 N1 C1 6.5(5) . . . . ? O5 Ce1 N1 C1 -156.5(4) . . . . ? O6 Ce1 N1 C1 -16.1(6) 3_855 . . . ? O7 Ce1 N1 C1 -67.2(5) . . . . ? C3 N1 C1 C2 0.8(8) . . . . ? Ce1 N1 C1 C2 -180.0(5) . . . . ? C3 N1 C1 C4 178.0(6) . . . . ? Ce1 N1 C1 C4 -2.8(8) . . . . ? N1 C1 C2 N2 0.5(8) . . . . ? C4 C1 C2 N2 -176.0(7) . . . . ? N1 C1 C2 C5 172.4(8) . . . . ? C4 C1 C2 C5 -4.1(14) . . . . ? C3 N2 C2 C1 -1.6(7) . . . . ? C3 N2 C2 C5 -175.2(6) . . . . ? C1 N1 C3 N2 -1.9(7) . . . . ? Ce1 N1 C3 N2 179.2(5) . . . . ? C1 N1 C3 C6 -178.4(6) . . . . ? Ce1 N1 C3 C6 2.7(11) . . . . ? C1 N1 C3 C6' -159.9(6) . . . . ? Ce1 N1 C3 C6' 21.2(10) . . . . ? C2 N2 C3 N1 2.3(8) . . . . ? C2 N2 C3 C6 179.2(5) . . . . ? C2 N2 C3 C6' 161.5(5) . . . . ? C7 C6 C3 N1 99.7(7) . . . . ? C7 C6 C3 N2 -76.6(8) . . . . ? C7 C6 C3 C6' 21.2(13) . . . . ? C7' C6' C3 N1 -122.9(7) . . . . ? C7' C6' C3 N2 80.8(8) . . . . ? C7' C6' C3 C6 -10.1(12) . . . . ? Ce1 O2 C4 O1 174.1(6) 4_566 . . . ? Ce1 O2 C4 C1 -7.2(13) 4_566 . . . ? Ce1 O1 C4 O2 -167.1(5) . . . . ? Ce1 O1 C4 C1 14.1(8) . . . . ? C2 C1 C4 O2 -8.5(12) . . . . ? N1 C1 C4 O2 175.2(6) . . . . ? C2 C1 C4 O1 170.2(7) . . . . ? N1 C1 C4 O1 -6.1(9) . . . . ? Ce1 O3 C5 O4 -131.2(7) 4_566 . . . ? Ce1 O3 C5 C2 54.1(11) 4_566 . . . ? Ce1 O4 C5 O3 23.5(13) 2_755 . . . ? Ce1 O4 C5 C2 -161.7(6) 2_755 . . . ? C1 C2 C5 O3 -2.6(13) . . . . ? N2 C2 C5 O3 168.4(6) . . . . ? C1 C2 C5 O4 -177.6(8) . . . . ? N2 C2 C5 O4 -6.6(10) . . . . ? Ce1 O6 C9 O5 -178.4(6) 3_855 . . . ? Ce1 O6 C9 C9 0.9(11) 3_855 . . 3_855 ? Ce1 O5 C9 O6 -178.8(6) . . . . ? Ce1 O5 C9 C9 1.8(10) . . . 3_855 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O8 0.86 2.00 2.849(9) 167.5 2_655 O7 H1W O9 0.83 1.91 2.736(10) 176.9 1_655 O8 H3W O1 0.83 1.90 2.730(8) 173.0 1_455 O8 H4W O9 0.83 2.21 2.923(10) 144.1 4_566 O9 H5W O5 0.83 2.33 3.162(9) 178.5 4_466 O9 H5W O6 0.83 2.64 3.211(9) 127.5 4_466 O9 H6W O8 0.84 1.91 2.747(10) 179.1 2_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 3.244 _refine_diff_density_min -2.148 _refine_diff_density_rms 0.236 # Attachment '- 1 sm.cif' data_b _database_code_depnum_ccdc_archive 'CCDC 765402' #TrackingRef '- 1 sm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H45 N8 O24 Sm3' _chemical_formula_weight 1388.82 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' 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 C2/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 35.099(4) _cell_length_b 9.2471(10) _cell_length_c 13.3141(14) _cell_angle_alpha 90.00 _cell_angle_beta 94.7770(10) _cell_angle_gamma 90.00 _cell_volume 4306.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5143 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.82 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2708 _exptl_absorpt_coefficient_mu 4.138 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3511 _exptl_absorpt_correction_T_max 0.6366 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15968 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3999 _reflns_number_gt 3513 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+11.8699P] 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 3999 _refine_ls_number_parameters 327 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0625 _refine_ls_wR_factor_gt 0.0589 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.034 _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 C17 C 0.0000 0.5000 0.5000 0.0388(11) Uani 0.409(14) 2 d SPDU . 1 H17A H 0.0064 0.4042 0.5244 0.047 Uiso 0.204(7) 1 d PR . 1 O9 O -0.0079(3) 0.5692(15) 0.5719(7) 0.0385(11) Uani 0.409(14) 1 d PDU . 1 C17' C 0.0000 0.5000 0.5000 0.0389(11) Uani 0.591(14) 2 d SPDU . 2 H17B H -0.0064 0.5958 0.4756 0.047 Uiso 0.296(7) 1 d PR . 2 O9' O -0.00438(19) 0.5054(12) 0.5840(4) 0.0383(11) Uani 0.591(14) 1 d PDU . 2 Sm1 Sm 0.110021(6) 0.07059(2) 0.629459(15) 0.01412(7) Uani 1 1 d . . . Sm2 Sm 0.0000 0.62361(3) 0.7500 0.01759(9) Uani 1 2 d S . . O1 O 0.10040(8) -0.0388(3) 0.7878(2) 0.0207(7) Uani 1 1 d . . . O2 O 0.10893(9) -0.0693(3) 0.9525(2) 0.0237(7) Uani 1 1 d . . . O3 O 0.17120(8) 0.0039(3) 1.0966(2) 0.0259(7) Uani 1 1 d . . . O4 O 0.22377(10) 0.1347(4) 1.0839(2) 0.0367(9) Uani 1 1 d . . . O5 O 0.07151(9) 0.2368(3) 0.7200(2) 0.0266(7) Uani 1 1 d . . . O6 O 0.04783(10) 0.4498(3) 0.7575(2) 0.0334(8) Uani 1 1 d . . . O7 O 0.04988(9) 0.7339(3) 0.6620(3) 0.0327(8) Uani 1 1 d . . . O8 O 0.09839(9) 0.8210(3) 0.5837(2) 0.0233(7) Uani 1 1 d . . . O10 O 0.04158(10) 0.0480(4) 0.5668(3) 0.0556(12) Uani 1 1 d . . . H1W H 0.0304 -0.0336 0.5691 0.083 Uiso 1 1 d R . . H2W H 0.0195 0.0770 0.5797 0.083 Uiso 1 1 d R . . O11 O -0.03458(10) 0.8107(4) 0.6505(3) 0.0437(10) Uani 1 1 d . . . H3W H -0.0408 0.8222 0.5877 0.066 Uiso 1 1 d R . . H4W H -0.0520 0.8582 0.6766 0.066 Uiso 1 1 d R . . O12 O -0.02453(13) 0.1768(6) 0.6082(4) 0.0796(16) Uani 1 1 d . . . H5W H -0.0189 0.2659 0.6022 0.119 Uiso 1 1 d R . . H6W H -0.0343 0.1861 0.6643 0.119 Uiso 1 1 d R . . N1 N 0.15482(10) 0.1644(4) 0.7829(3) 0.0193(8) Uani 1 1 d . . . N2 N 0.20103(11) 0.2276(4) 0.8960(3) 0.0240(8) Uani 1 1 d . . . H2 H 0.2213 0.2696 0.9225 0.029 Uiso 1 1 calc R . . N3 N 0.11263(10) 0.3408(4) 0.5754(3) 0.0204(8) Uani 1 1 d . . . N4 N 0.11859(11) 0.5607(4) 0.5175(3) 0.0255(9) Uani 1 1 d . . . H4 H 0.1264 0.6312 0.4824 0.031 Uiso 1 1 calc R . . C1 C 0.14989(12) 0.0929(4) 0.8732(3) 0.0166(9) Uani 1 1 d . . . C2 C 0.17890(12) 0.1317(5) 0.9443(3) 0.0194(9) Uani 1 1 d . . . C3 C 0.18573(13) 0.2453(5) 0.8000(3) 0.0233(10) Uani 1 1 d . . . C4 C 0.11775(12) -0.0112(4) 0.8731(3) 0.0171(9) Uani 1 1 d . . . C5 C 0.19260(13) 0.0874(5) 1.0507(3) 0.0213(10) Uani 1 1 d . . . C6 C 0.20296(15) 0.3452(6) 0.7289(4) 0.0350(12) Uani 1 1 d . . . H6A H 0.2153 0.4240 0.7672 0.042 Uiso 1 1 calc R . . H6B H 0.1826 0.3864 0.6840 0.042 Uiso 1 1 calc R . . C7 C 0.2315(2) 0.2771(7) 0.6669(5) 0.0602(18) Uani 1 1 d . . . H7A H 0.2185 0.2107 0.6191 0.072 Uiso 1 1 calc R . . H7B H 0.2497 0.2221 0.7103 0.072 Uiso 1 1 calc R . . C8 C 0.2526(2) 0.3911(8) 0.6101(5) 0.070(2) Uani 1 1 d . . . H8A H 0.2345 0.4500 0.5708 0.105 Uiso 1 1 calc R . . H8B H 0.2692 0.3443 0.5663 0.105 Uiso 1 1 calc R . . H8C H 0.2676 0.4508 0.6575 0.105 Uiso 1 1 calc R . . C9 C 0.08932(12) 0.4335(4) 0.6253(3) 0.0168(9) Uani 1 1 d . . . C10 C 0.09273(12) 0.5718(4) 0.5899(3) 0.0196(9) Uani 1 1 d . . . C11 C 0.12977(13) 0.4210(4) 0.5106(3) 0.0221(10) Uani 1 1 d . . . C12 C 0.06749(12) 0.3707(5) 0.7061(3) 0.0205(9) Uani 1 1 d . . . C13 C 0.07847(13) 0.7195(4) 0.6146(3) 0.0198(9) Uani 1 1 d . . . C14 C 0.15719(13) 0.3701(5) 0.4390(3) 0.0265(10) Uani 1 1 d . . . H14A H 0.1643 0.2709 0.4552 0.032 Uiso 1 1 calc R . . H14B H 0.1802 0.4286 0.4474 0.032 Uiso 1 1 calc R . . C15 C 0.14091(14) 0.3777(6) 0.3293(3) 0.0317(11) Uani 1 1 d . . . H15A H 0.1377 0.4781 0.3093 0.038 Uiso 1 1 calc R . . H15B H 0.1160 0.3319 0.3225 0.038 Uiso 1 1 calc R . . C16 C 0.16731(16) 0.3025(6) 0.2601(4) 0.0424(14) Uani 1 1 d . . . H16A H 0.1925 0.3436 0.2701 0.064 Uiso 1 1 calc R . . H16B H 0.1575 0.3154 0.1912 0.064 Uiso 1 1 calc R . . H16C H 0.1685 0.2011 0.2756 0.064 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 C17 0.0390(12) 0.0396(12) 0.0379(12) -0.0012(6) 0.0034(7) 0.0001(7) O9 0.0388(12) 0.0393(12) 0.0374(12) -0.0010(6) 0.0036(6) 0.0001(7) C17' 0.0391(12) 0.0398(12) 0.0378(12) -0.0013(7) 0.0034(7) 0.0001(7) O9' 0.0387(12) 0.0393(12) 0.0372(12) -0.0010(6) 0.0038(6) 0.0001(7) Sm1 0.01788(13) 0.01334(12) 0.01131(12) 0.00043(8) 0.00235(8) 0.00111(8) Sm2 0.01832(17) 0.01725(17) 0.01775(17) 0.000 0.00483(13) 0.000 O1 0.0255(17) 0.0197(15) 0.0162(15) 0.0020(12) -0.0027(13) -0.0078(13) O2 0.0306(18) 0.0240(17) 0.0169(16) 0.0032(12) 0.0048(14) -0.0082(13) O3 0.0198(17) 0.0353(19) 0.0227(16) 0.0078(14) 0.0022(13) -0.0020(14) O4 0.0265(19) 0.058(2) 0.0240(18) 0.0045(16) -0.0048(15) -0.0173(17) O5 0.0368(19) 0.0140(16) 0.0311(18) 0.0026(13) 0.0150(15) 0.0062(14) O6 0.047(2) 0.0263(18) 0.0304(18) 0.0041(14) 0.0221(17) 0.0160(16) O7 0.033(2) 0.0207(17) 0.047(2) -0.0031(15) 0.0225(17) 0.0006(14) O8 0.0317(18) 0.0141(15) 0.0256(17) -0.0015(12) 0.0107(14) -0.0042(13) O10 0.019(2) 0.042(2) 0.105(4) -0.031(2) -0.004(2) 0.0044(16) O11 0.043(2) 0.056(2) 0.033(2) 0.0144(17) 0.0096(17) 0.0280(19) O12 0.059(3) 0.085(4) 0.099(4) -0.039(3) 0.030(3) 0.005(3) N1 0.021(2) 0.0198(19) 0.0173(18) 0.0004(14) 0.0025(15) -0.0041(15) N2 0.022(2) 0.029(2) 0.020(2) 0.0017(16) -0.0022(16) -0.0082(16) N3 0.026(2) 0.0189(19) 0.0166(18) -0.0002(14) 0.0053(15) 0.0019(16) N4 0.035(2) 0.0150(19) 0.029(2) 0.0008(15) 0.0172(18) -0.0013(16) C1 0.016(2) 0.020(2) 0.013(2) 0.0007(16) 0.0022(17) 0.0009(17) C2 0.019(2) 0.021(2) 0.019(2) 0.0007(17) 0.0039(18) -0.0015(18) C3 0.022(2) 0.025(2) 0.023(2) 0.0033(19) 0.0039(19) -0.005(2) C4 0.023(2) 0.013(2) 0.016(2) -0.0053(16) 0.0011(18) 0.0011(17) C5 0.023(2) 0.024(2) 0.017(2) -0.0034(18) 0.0026(19) -0.0031(19) C6 0.034(3) 0.038(3) 0.033(3) 0.011(2) 0.002(2) -0.009(2) C7 0.069(5) 0.050(4) 0.067(4) 0.003(3) 0.037(4) -0.005(3) C8 0.061(5) 0.085(5) 0.069(5) 0.017(4) 0.034(4) -0.016(4) C9 0.021(2) 0.016(2) 0.014(2) -0.0028(16) 0.0006(17) 0.0030(17) C10 0.021(2) 0.019(2) 0.019(2) -0.0016(17) 0.0045(18) -0.0001(18) C11 0.025(2) 0.019(2) 0.023(2) -0.0016(18) 0.0057(19) 0.0033(18) C12 0.021(2) 0.018(2) 0.023(2) 0.0002(18) -0.0011(19) 0.0021(18) C13 0.025(2) 0.015(2) 0.018(2) -0.0027(17) -0.0004(19) 0.0012(18) C14 0.028(3) 0.022(2) 0.032(3) 0.002(2) 0.013(2) -0.001(2) C15 0.030(3) 0.039(3) 0.027(3) 0.002(2) 0.007(2) 0.001(2) C16 0.039(3) 0.054(4) 0.036(3) -0.005(3) 0.012(3) 0.001(3) _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 C17 O9 1.203(7) 5_566 ? C17 O9 1.203(7) . ? C17 H17A 0.9635 . ? C17 H17B 0.9635 . ? O9 Sm2 2.417(8) . ? C17' O9' 1.143(5) 5_566 ? C17' O9' 1.143(5) . ? C17' H17A 0.9635 . ? C17' H17B 0.9635 . ? O9' Sm2 2.459(6) . ? Sm1 O3 2.331(3) 6 ? Sm1 O2 2.353(3) 6 ? Sm1 O1 2.387(3) . ? Sm1 O8 2.413(3) 1_545 ? Sm1 O5 2.432(3) . ? Sm1 O10 2.485(4) . ? Sm1 N3 2.604(3) . ? Sm1 N1 2.620(3) . ? Sm2 O6 2.321(3) 2_556 ? Sm2 O6 2.321(3) . ? Sm2 O7 2.413(3) 2_556 ? Sm2 O7 2.413(3) . ? Sm2 O9 2.417(8) 2_556 ? Sm2 O11 2.440(3) 2_556 ? Sm2 O11 2.440(3) . ? Sm2 O9' 2.459(6) 2_556 ? O1 C4 1.270(5) . ? O2 C4 1.247(5) . ? O2 Sm1 2.353(3) 6_556 ? O3 C5 1.269(5) . ? O3 Sm1 2.331(3) 6_556 ? O4 C5 1.226(5) . ? O5 C12 1.257(5) . ? O6 C12 1.248(5) . ? O7 C13 1.236(5) . ? O8 C13 1.260(5) . ? O8 Sm1 2.413(3) 1_565 ? O10 O12 2.705(5) . ? O10 H1W 0.8525 . ? O10 H2W 0.8508 . ? O11 H3W 0.8534 . ? O11 H4W 0.8514 . ? O12 H5W 0.8528 . ? O12 H6W 0.8522 . ? N1 C3 1.322(5) . ? N1 C1 1.396(5) . ? N2 C3 1.355(5) . ? N2 C2 1.373(5) . ? N2 H2 0.8600 . ? N3 C11 1.320(5) . ? N3 C9 1.391(5) . ? N4 C11 1.355(5) . ? N4 C10 1.381(5) . ? N4 H4 0.8600 . ? C1 C2 1.379(6) . ? C1 C4 1.483(6) . ? C2 C5 1.515(6) . ? C3 C6 1.487(6) . ? C6 C7 1.488(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.527(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.372(6) . ? C9 C12 1.490(6) . ? C10 C13 1.500(6) . ? C11 C14 1.487(6) . ? C14 C15 1.525(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.528(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 O9 C17 O9 180.0(9) 5_566 . ? O9 C17 H17A 73.6 5_566 . ? O9 C17 H17A 106.4 . . ? O9 C17 H17B 106.4 5_566 . ? O9 C17 H17B 73.6 . . ? H17A C17 H17B 180.0 . . ? C17 O9 Sm2 151.2(10) . . ? C17 O9 H17B 44.8 . . ? Sm2 O9 H17B 155.5 . . ? O9' C17' O9' 180.0(7) 5_566 . ? O9' C17' H17A 104.1 5_566 . ? O9' C17' H17A 75.9 . . ? O9' C17' H17B 75.9 5_566 . ? O9' C17' H17B 104.1 . . ? H17A C17' H17B 180.0 . . ? C17' O9' Sm2 153.6(7) . . ? C17' O9' H17A 45.8 . . ? Sm2 O9' H17A 150.1 . . ? O3 Sm1 O2 75.46(10) 6 6 ? O3 Sm1 O1 103.94(11) 6 . ? O2 Sm1 O1 152.90(10) 6 . ? O3 Sm1 O8 79.00(11) 6 1_545 ? O2 Sm1 O8 75.76(10) 6 1_545 ? O1 Sm1 O8 77.55(10) . 1_545 ? O3 Sm1 O5 146.98(11) 6 . ? O2 Sm1 O5 122.40(10) 6 . ? O1 Sm1 O5 72.84(10) . . ? O8 Sm1 O5 129.83(10) 1_545 . ? O3 Sm1 O10 142.37(12) 6 . ? O2 Sm1 O10 74.26(13) 6 . ? O1 Sm1 O10 93.27(13) . . ? O8 Sm1 O10 72.33(11) 1_545 . ? O5 Sm1 O10 69.99(12) . . ? O3 Sm1 N3 100.23(11) 6 . ? O2 Sm1 N3 74.11(10) 6 . ? O1 Sm1 N3 131.40(10) . . ? O8 Sm1 N3 148.99(10) 1_545 . ? O5 Sm1 N3 64.15(10) . . ? O10 Sm1 N3 92.46(12) . . ? O3 Sm1 N1 75.03(11) 6 . ? O2 Sm1 N1 137.81(11) 6 . ? O1 Sm1 N1 64.65(10) . . ? O8 Sm1 N1 126.28(11) 1_545 . ? O5 Sm1 N1 74.13(11) . . ? O10 Sm1 N1 142.20(12) . . ? N3 Sm1 N1 82.23(11) . . ? O6 Sm2 O6 92.30(17) 2_556 . ? O6 Sm2 O7 76.24(11) 2_556 2_556 ? O6 Sm2 O7 145.44(11) . 2_556 ? O6 Sm2 O7 145.44(11) 2_556 . ? O6 Sm2 O7 76.24(11) . . ? O7 Sm2 O7 129.99(15) 2_556 . ? O6 Sm2 O9 77.9(3) 2_556 . ? O6 Sm2 O9 85.5(3) . . ? O7 Sm2 O9 122.4(3) 2_556 . ? O7 Sm2 O9 68.9(3) . . ? O6 Sm2 O9 85.5(3) 2_556 2_556 ? O6 Sm2 O9 77.9(3) . 2_556 ? O7 Sm2 O9 68.9(3) 2_556 2_556 ? O7 Sm2 O9 122.4(3) . 2_556 ? O9 Sm2 O9 156.0(7) . 2_556 ? O6 Sm2 O11 147.14(11) 2_556 2_556 ? O6 Sm2 O11 98.18(13) . 2_556 ? O7 Sm2 O11 77.58(12) 2_556 2_556 ? O7 Sm2 O11 67.41(11) . 2_556 ? O9 Sm2 O11 133.7(3) . 2_556 ? O9 Sm2 O11 66.7(3) 2_556 2_556 ? O6 Sm2 O11 98.18(13) 2_556 . ? O6 Sm2 O11 147.14(11) . . ? O7 Sm2 O11 67.41(11) 2_556 . ? O7 Sm2 O11 77.58(12) . . ? O9 Sm2 O11 66.7(3) . . ? O9 Sm2 O11 133.7(3) 2_556 . ? O11 Sm2 O11 89.70(19) 2_556 . ? O6 Sm2 O9' 70.26(19) 2_556 . ? O6 Sm2 O9' 73.8(2) . . ? O7 Sm2 O9' 129.12(19) 2_556 . ? O7 Sm2 O9' 75.22(19) . . ? O9 Sm2 O9' 14.6(2) . . ? O9 Sm2 O9' 141.5(6) 2_556 . ? O11 Sm2 O9' 142.6(2) 2_556 . ? O11 Sm2 O9' 80.6(3) . . ? O6 Sm2 O9' 73.8(2) 2_556 2_556 ? O6 Sm2 O9' 70.26(19) . 2_556 ? O7 Sm2 O9' 75.22(19) 2_556 2_556 ? O7 Sm2 O9' 129.12(19) . 2_556 ? O9 Sm2 O9' 141.5(6) . 2_556 ? O9 Sm2 O9' 14.6(2) 2_556 2_556 ? O11 Sm2 O9' 80.6(3) 2_556 2_556 ? O11 Sm2 O9' 142.59(19) . 2_556 ? O9' Sm2 O9' 127.2(5) . 2_556 ? C4 O1 Sm1 127.8(3) . . ? C4 O2 Sm1 150.0(3) . 6_556 ? C5 O3 Sm1 149.5(3) . 6_556 ? C12 O5 Sm1 127.6(3) . . ? C12 O6 Sm2 144.4(3) . . ? C13 O7 Sm2 148.8(3) . . ? C13 O8 Sm1 135.8(3) . 1_565 ? Sm1 O10 O12 135.73(18) . . ? Sm1 O10 H1W 119.7 . . ? O12 O10 H1W 88.8 . . ? Sm1 O10 H2W 140.9 . . ? O12 O10 H2W 7.8 . . ? H1W O10 H2W 81.0 . . ? Sm2 O11 H3W 134.0 . . ? Sm2 O11 H4W 119.2 . . ? H3W O11 H4W 101.7 . . ? O10 O12 H5W 101.3 . . ? O10 O12 H6W 129.6 . . ? H5W O12 H6W 95.7 . . ? C3 N1 C1 106.2(3) . . ? C3 N1 Sm1 138.8(3) . . ? C1 N1 Sm1 113.9(3) . . ? C3 N2 C2 108.9(4) . . ? C3 N2 H2 125.5 . . ? C2 N2 H2 125.5 . . ? C11 N3 C9 106.5(3) . . ? C11 N3 Sm1 138.4(3) . . ? C9 N3 Sm1 115.1(3) . . ? C11 N4 C10 109.2(4) . . ? C11 N4 H4 125.4 . . ? C10 N4 H4 125.4 . . ? C2 C1 N1 109.3(4) . . ? C2 C1 C4 133.5(4) . . ? N1 C1 C4 117.1(3) . . ? N2 C2 C1 105.2(4) . . ? N2 C2 C5 117.7(4) . . ? C1 C2 C5 136.9(4) . . ? N1 C3 N2 110.5(4) . . ? N1 C3 C6 127.8(4) . . ? N2 C3 C6 121.7(4) . . ? O2 C4 O1 122.5(4) . . ? O2 C4 C1 121.4(4) . . ? O1 C4 C1 116.1(4) . . ? O4 C5 O3 126.2(4) . . ? O4 C5 C2 116.4(4) . . ? O3 C5 C2 117.4(4) . . ? C3 C6 C7 114.7(5) . . ? C3 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C3 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 111.1(5) . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N3 109.8(4) . . ? C10 C9 C12 132.6(4) . . ? N3 C9 C12 117.6(3) . . ? C9 C10 N4 104.6(4) . . ? C9 C10 C13 137.2(4) . . ? N4 C10 C13 118.1(4) . . ? N3 C11 N4 109.9(4) . . ? N3 C11 C14 126.6(4) . . ? N4 C11 C14 123.5(4) . . ? O6 C12 O5 123.8(4) . . ? O6 C12 C9 120.6(4) . . ? O5 C12 C9 115.6(4) . . ? O7 C13 O8 125.6(4) . . ? O7 C13 C10 120.6(4) . . ? O8 C13 C10 113.7(4) . . ? C11 C14 C15 112.9(4) . . ? C11 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C11 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 C16 111.0(4) . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O9 C17 O9 Sm2 -28(100) 5_566 . . . ? O9' C17' O9' Sm2 67(8) 5_566 . . . ? C17 O9 Sm2 O6 -89.3(17) . . . 2_556 ? C17 O9 Sm2 O6 4.0(17) . . . . ? C17 O9 Sm2 O7 -154.2(15) . . . 2_556 ? C17 O9 Sm2 O7 81.0(16) . . . . ? C17 O9 Sm2 O9 -42.1(17) . . . 2_556 ? C17 O9 Sm2 O11 101.0(18) . . . 2_556 ? C17 O9 Sm2 O11 166.1(18) . . . . ? C17 O9 Sm2 O9' -32.4(13) . . . . ? C17 O9 Sm2 O9' -45.9(19) . . . 2_556 ? C17' O9' Sm2 O6 157.2(14) . . . 2_556 ? C17' O9' Sm2 O6 -104.3(13) . . . . ? C17' O9' Sm2 O7 105.3(12) . . . 2_556 ? C17' O9' Sm2 O7 -24.6(13) . . . . ? C17' O9' Sm2 O9 37.6(13) . . . . ? C17' O9' Sm2 O9 -148.7(13) . . . 2_556 ? C17' O9' Sm2 O11 -22.1(16) . . . 2_556 ? C17' O9' Sm2 O11 54.9(14) . . . . ? C17' O9' Sm2 O9' -152.9(14) . . . 2_556 ? O3 Sm1 O1 C4 66.9(3) 6 . . . ? O2 Sm1 O1 C4 152.2(3) 6 . . . ? O8 Sm1 O1 C4 142.1(3) 1_545 . . . ? O5 Sm1 O1 C4 -78.9(3) . . . . ? O10 Sm1 O1 C4 -146.8(3) . . . . ? N3 Sm1 O1 C4 -50.6(4) . . . . ? N1 Sm1 O1 C4 1.2(3) . . . . ? O3 Sm1 O5 C12 69.1(4) 6 . . . ? O2 Sm1 O5 C12 -46.5(4) 6 . . . ? O1 Sm1 O5 C12 158.4(4) . . . . ? O8 Sm1 O5 C12 -145.1(3) 1_545 . . . ? O10 Sm1 O5 C12 -101.5(4) . . . . ? N3 Sm1 O5 C12 1.6(3) . . . . ? N1 Sm1 O5 C12 90.6(4) . . . . ? O6 Sm2 O6 C12 86.9(5) 2_556 . . . ? O7 Sm2 O6 C12 155.7(5) 2_556 . . . ? O7 Sm2 O6 C12 -60.1(5) . . . . ? O9 Sm2 O6 C12 9.3(6) . . . . ? O9 Sm2 O6 C12 171.8(6) 2_556 . . . ? O11 Sm2 O6 C12 -124.3(5) 2_556 . . . ? O11 Sm2 O6 C12 -22.0(7) . . . . ? O9' Sm2 O6 C12 18.2(6) . . . . ? O9' Sm2 O6 C12 158.8(6) 2_556 . . . ? O6 Sm2 O7 C13 -50.8(7) 2_556 . . . ? O6 Sm2 O7 C13 22.8(6) . . . . ? O7 Sm2 O7 C13 177.1(6) 2_556 . . . ? O9 Sm2 O7 C13 -67.7(7) . . . . ? O9 Sm2 O7 C13 88.5(7) 2_556 . . . ? O11 Sm2 O7 C13 127.9(6) 2_556 . . . ? O11 Sm2 O7 C13 -137.2(6) . . . . ? O9' Sm2 O7 C13 -53.8(6) . . . . ? O9' Sm2 O7 C13 72.4(7) 2_556 . . . ? O3 Sm1 O10 O12 -170.5(2) 6 . . . ? O2 Sm1 O10 O12 -133.0(3) 6 . . . ? O1 Sm1 O10 O12 71.5(3) . . . . ? O8 Sm1 O10 O12 147.3(3) 1_545 . . . ? O5 Sm1 O10 O12 1.1(3) . . . . ? N3 Sm1 O10 O12 -60.2(3) . . . . ? N1 Sm1 O10 O12 20.2(4) . . . . ? O3 Sm1 N1 C3 55.3(4) 6 . . . ? O2 Sm1 N1 C3 8.3(5) 6 . . . ? O1 Sm1 N1 C3 169.1(5) . . . . ? O8 Sm1 N1 C3 119.1(4) 1_545 . . . ? O5 Sm1 N1 C3 -112.8(5) . . . . ? O10 Sm1 N1 C3 -131.5(4) . . . . ? N3 Sm1 N1 C3 -47.5(4) . . . . ? O3 Sm1 N1 C1 -110.5(3) 6 . . . ? O2 Sm1 N1 C1 -157.5(2) 6 . . . ? O1 Sm1 N1 C1 3.3(3) . . . . ? O8 Sm1 N1 C1 -46.6(3) 1_545 . . . ? O5 Sm1 N1 C1 81.5(3) . . . . ? O10 Sm1 N1 C1 62.8(4) . . . . ? N3 Sm1 N1 C1 146.7(3) . . . . ? O3 Sm1 N3 C11 29.8(5) 6 . . . ? O2 Sm1 N3 C11 -41.7(4) 6 . . . ? O1 Sm1 N3 C11 148.9(4) . . . . ? O8 Sm1 N3 C11 -55.8(5) 1_545 . . . ? O5 Sm1 N3 C11 179.1(5) . . . . ? O10 Sm1 N3 C11 -114.6(5) . . . . ? N1 Sm1 N3 C11 103.0(5) . . . . ? O3 Sm1 N3 C9 -151.6(3) 6 . . . ? O2 Sm1 N3 C9 136.9(3) 6 . . . ? O1 Sm1 N3 C9 -32.6(3) . . . . ? O8 Sm1 N3 C9 122.8(3) 1_545 . . . ? O5 Sm1 N3 C9 -2.3(3) . . . . ? O10 Sm1 N3 C9 64.0(3) . . . . ? N1 Sm1 N3 C9 -78.4(3) . . . . ? C3 N1 C1 C2 -0.7(5) . . . . ? Sm1 N1 C1 C2 169.6(3) . . . . ? C3 N1 C1 C4 -177.3(4) . . . . ? Sm1 N1 C1 C4 -7.0(4) . . . . ? C3 N2 C2 C1 0.1(5) . . . . ? C3 N2 C2 C5 175.4(4) . . . . ? N1 C1 C2 N2 0.4(5) . . . . ? C4 C1 C2 N2 176.2(4) . . . . ? N1 C1 C2 C5 -173.6(5) . . . . ? C4 C1 C2 C5 2.2(9) . . . . ? C1 N1 C3 N2 0.8(5) . . . . ? Sm1 N1 C3 N2 -165.7(3) . . . . ? C1 N1 C3 C6 -178.6(5) . . . . ? Sm1 N1 C3 C6 14.9(8) . . . . ? C2 N2 C3 N1 -0.6(5) . . . . ? C2 N2 C3 C6 178.9(4) . . . . ? Sm1 O2 C4 O1 -160.0(4) 6_556 . . . ? Sm1 O2 C4 C1 21.2(8) 6_556 . . . ? Sm1 O1 C4 O2 175.8(3) . . . . ? Sm1 O1 C4 C1 -5.3(5) . . . . ? C2 C1 C4 O2 11.5(7) . . . . ? N1 C1 C4 O2 -172.9(4) . . . . ? C2 C1 C4 O1 -167.4(4) . . . . ? N1 C1 C4 O1 8.2(6) . . . . ? Sm1 O3 C5 O4 145.6(5) 6_556 . . . ? Sm1 O3 C5 C2 -35.5(8) 6_556 . . . ? N2 C2 C5 O4 -4.0(6) . . . . ? C1 C2 C5 O4 169.4(5) . . . . ? N2 C2 C5 O3 176.9(4) . . . . ? C1 C2 C5 O3 -9.7(8) . . . . ? N1 C3 C6 C7 -89.1(7) . . . . ? N2 C3 C6 C7 91.5(6) . . . . ? C3 C6 C7 C8 -170.1(5) . . . . ? C11 N3 C9 C10 -0.3(5) . . . . ? Sm1 N3 C9 C10 -179.3(3) . . . . ? C11 N3 C9 C12 -177.9(4) . . . . ? Sm1 N3 C9 C12 3.1(5) . . . . ? N3 C9 C10 N4 0.0(5) . . . . ? C12 C9 C10 N4 177.2(4) . . . . ? N3 C9 C10 C13 -174.7(5) . . . . ? C12 C9 C10 C13 2.4(9) . . . . ? C11 N4 C10 C9 0.2(5) . . . . ? C11 N4 C10 C13 176.2(4) . . . . ? C9 N3 C11 N4 0.4(5) . . . . ? Sm1 N3 C11 N4 179.1(3) . . . . ? C9 N3 C11 C14 -179.2(4) . . . . ? Sm1 N3 C11 C14 -0.5(8) . . . . ? C10 N4 C11 N3 -0.4(5) . . . . ? C10 N4 C11 C14 179.2(4) . . . . ? Sm2 O6 C12 O5 -129.5(5) . . . . ? Sm2 O6 C12 C9 53.1(7) . . . . ? Sm1 O5 C12 O6 -178.2(3) . . . . ? Sm1 O5 C12 C9 -0.7(6) . . . . ? C10 C9 C12 O6 -1.2(8) . . . . ? N3 C9 C12 O6 175.8(4) . . . . ? C10 C9 C12 O5 -178.8(5) . . . . ? N3 C9 C12 O5 -1.8(6) . . . . ? Sm2 O7 C13 O8 -176.0(4) . . . . ? Sm2 O7 C13 C10 3.2(8) . . . . ? Sm1 O8 C13 O7 22.8(7) 1_565 . . . ? Sm1 O8 C13 C10 -156.4(3) 1_565 . . . ? C9 C10 C13 O7 -21.0(8) . . . . ? N4 C10 C13 O7 164.8(4) . . . . ? C9 C10 C13 O8 158.3(5) . . . . ? N4 C10 C13 O8 -15.9(6) . . . . ? N3 C11 C14 C15 111.0(5) . . . . ? N4 C11 C14 C15 -68.5(6) . . . . ? C11 C14 C15 C16 -170.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O10 H1W O7 0.85 2.54 3.173(5) 131.4 1_545 O10 H2W O12 0.85 1.87 2.705(5) 168.7 . O11 H3W O10 0.85 2.38 3.165(6) 153.4 5_566 O11 H3W O2 0.85 2.61 3.054(5) 113.7 2_566 O11 H4W O1 0.85 2.04 2.875(4) 168.1 2_566 O11 H3W O2 0.85 2.61 3.054(5) 113.7 2_566 O12 H5W O9' 0.85 2.29 3.142(12) 179.2 . O12 H6W O5 0.85 2.15 2.982(5) 164.2 2_556 N2 H2 O4 0.86 2.13 2.923(5) 153.2 7_557 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.225 _refine_diff_density_min -1.585 _refine_diff_density_rms 0.127 # Attachment '- 2.eu.cif' data_2eu _database_code_depnum_ccdc_archive 'CCDC 765403' #TrackingRef '- 2.eu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 Eu2 N5.33 O16' _chemical_formula_weight 929.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 35.038(10) _cell_length_b 9.216(3) _cell_length_c 13.265(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.780(3) _cell_angle_gamma 90.00 _cell_volume 4268(2) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6203 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.22 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2720 _exptl_absorpt_coefficient_mu 4.455 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3046 _exptl_absorpt_correction_T_max 0.4848 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14995 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3955 _reflns_number_gt 3306 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1091P)^2^+7.1468P] 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 3955 _refine_ls_number_parameters 327 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1556 _refine_ls_wR_factor_gt 0.1450 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.067 _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 C17 C 0.0000 0.5000 0.5000 0.037(2) Uani 0.44(3) 2 d SPDU . 1 H17A H 0.0064 0.4042 0.5244 0.045 Uiso 0.219(13) 1 d PR . 1 O9 O -0.0084(5) 0.566(3) 0.5734(13) 0.037(2) Uani 0.44(3) 1 d PDU . 1 C17' C 0.0000 0.5000 0.5000 0.037(2) Uani 0.56(3) 2 d SPDU . 2 H17B H -0.0064 0.5958 0.4756 0.045 Uiso 0.281(13) 1 d PR . 2 O9' O -0.0043(4) 0.502(2) 0.5869(7) 0.037(2) Uani 0.56(3) 1 d PDU . 2 Eu1 Eu 0.109809(12) 0.07024(4) 0.62953(3) 0.01443(18) Uani 1 1 d . . . Eu2 Eu 0.0000 0.62267(7) 0.7500 0.0183(2) Uani 1 2 d S . . O1 O 0.10000(18) -0.0395(7) 0.7868(4) 0.0208(13) Uani 1 1 d . . . O2 O 0.10818(19) -0.0688(7) 0.9519(5) 0.0240(15) Uani 1 1 d . . . O3 O 0.17078(18) 0.0036(8) 1.0963(5) 0.0257(14) Uani 1 1 d . . . O4 O 0.2235(2) 0.1350(9) 1.0843(5) 0.0376(18) Uani 1 1 d . . . O5 O 0.07121(19) 0.2358(7) 0.7202(5) 0.0274(15) Uani 1 1 d . . . O6 O 0.0475(2) 0.4463(7) 0.7575(5) 0.0351(18) Uani 1 1 d . . . O7 O 0.0498(2) 0.7339(7) 0.6626(6) 0.0327(17) Uani 1 1 d . . . O8 O 0.09840(18) 0.8219(7) 0.5848(5) 0.0227(14) Uani 1 1 d . . . O10 O 0.0418(2) 0.0474(9) 0.5667(7) 0.053(2) Uani 1 1 d . . . H1W H 0.0306 -0.0343 0.5690 0.080 Uiso 1 1 d R . . H2W H 0.0197 0.0763 0.5796 0.080 Uiso 1 1 d R . . O11 O -0.0341(2) 0.8110(9) 0.6514(5) 0.042(2) Uani 1 1 d . . . H3W H -0.0403 0.8225 0.5886 0.062 Uiso 1 1 d R . . H4W H -0.0516 0.8586 0.6775 0.062 Uiso 1 1 d R . . O12 O -0.0245(3) 0.1763(13) 0.6074(8) 0.082(4) Uani 1 1 d . . . H5W H -0.0189 0.2653 0.6014 0.123 Uiso 1 1 d R . . H6W H -0.0343 0.1856 0.6636 0.123 Uiso 1 1 d R . . N1 N 0.1547(2) 0.1646(9) 0.7826(5) 0.0217(16) Uani 1 1 d . . . N2 N 0.2008(2) 0.2276(9) 0.8962(6) 0.0249(17) Uani 1 1 d . . . H2 H 0.2211 0.2694 0.9228 0.030 Uiso 1 1 calc R . . N3 N 0.1125(2) 0.3392(8) 0.5758(5) 0.0203(16) Uani 1 1 d . . . N4 N 0.1181(2) 0.5596(8) 0.5169(6) 0.0243(18) Uani 1 1 d . . . H4 H 0.1258 0.6301 0.4813 0.029 Uiso 1 1 calc R . . C1 C 0.1495(2) 0.0938(9) 0.8731(6) 0.0159(17) Uani 1 1 d . . . C2 C 0.1784(2) 0.1309(10) 0.9449(6) 0.0201(19) Uani 1 1 d . . . C3 C 0.1856(2) 0.2461(11) 0.7997(7) 0.0221(19) Uani 1 1 d . . . C4 C 0.1170(2) -0.0116(9) 0.8731(6) 0.0154(17) Uani 1 1 d . . . C5 C 0.1923(3) 0.0864(11) 1.0515(7) 0.023(2) Uani 1 1 d . . . C6 C 0.2029(3) 0.3472(12) 0.7277(8) 0.035(2) Uani 1 1 d . . . H6A H 0.1826 0.3875 0.6819 0.042 Uiso 1 1 calc R . . H6B H 0.2150 0.4270 0.7658 0.042 Uiso 1 1 calc R . . C7 C 0.2313(4) 0.2787(16) 0.6679(12) 0.063(4) Uani 1 1 d . . . H7A H 0.2183 0.2115 0.6203 0.076 Uiso 1 1 calc R . . H7B H 0.2491 0.2235 0.7127 0.076 Uiso 1 1 calc R . . C8 C 0.2533(4) 0.3874(17) 0.6104(12) 0.067(4) Uani 1 1 d . . . H8A H 0.2359 0.4402 0.5643 0.101 Uiso 1 1 calc R . . H8B H 0.2717 0.3374 0.5733 0.101 Uiso 1 1 calc R . . H8C H 0.2664 0.4538 0.6572 0.101 Uiso 1 1 calc R . . C9 C 0.0890(3) 0.4322(9) 0.6258(6) 0.0174(18) Uani 1 1 d . . . C10 C 0.0925(3) 0.5719(9) 0.5888(8) 0.024(2) Uani 1 1 d . . . C11 C 0.1295(3) 0.4204(10) 0.5102(8) 0.027(2) Uani 1 1 d . . . C12 C 0.0672(3) 0.3700(9) 0.7055(6) 0.0181(18) Uani 1 1 d . . . C13 C 0.0789(3) 0.7201(10) 0.6151(6) 0.0202(19) Uani 1 1 d . . . C14 C 0.1571(3) 0.3685(11) 0.4389(7) 0.027(2) Uani 1 1 d . . . H14A H 0.1639 0.2686 0.4550 0.033 Uiso 1 1 calc R . . H14B H 0.1803 0.4261 0.4484 0.033 Uiso 1 1 calc R . . C15 C 0.1415(3) 0.3776(13) 0.3288(7) 0.033(2) Uani 1 1 d . . . H15A H 0.1164 0.3324 0.3209 0.039 Uiso 1 1 calc R . . H15B H 0.1386 0.4787 0.3094 0.039 Uiso 1 1 calc R . . C16 C 0.1675(3) 0.3039(14) 0.2599(9) 0.043(3) Uani 1 1 d . . . H16A H 0.1931 0.3404 0.2732 0.065 Uiso 1 1 calc R . . H16B H 0.1587 0.3233 0.1908 0.065 Uiso 1 1 calc R . . H16C H 0.1673 0.2012 0.2717 0.065 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 C17 0.037(2) 0.037(2) 0.037(2) -0.0002(6) 0.0031(7) 0.0000(7) O9 0.037(2) 0.037(2) 0.037(2) -0.0001(6) 0.0031(7) 0.0000(7) C17' 0.037(2) 0.037(2) 0.037(2) -0.0002(7) 0.0031(7) 0.0000(7) O9' 0.037(2) 0.037(2) 0.037(2) -0.0002(7) 0.0032(7) 0.0000(7) Eu1 0.0183(3) 0.0141(3) 0.0111(3) 0.00066(15) 0.00297(17) 0.00114(15) Eu2 0.0192(4) 0.0186(4) 0.0178(3) 0.000 0.0053(2) 0.000 O1 0.025(3) 0.020(3) 0.016(3) -0.003(2) -0.004(2) -0.008(3) O2 0.030(4) 0.025(4) 0.017(3) 0.002(2) 0.004(3) -0.008(3) O3 0.021(3) 0.035(4) 0.021(3) 0.008(3) 0.002(3) -0.003(3) O4 0.025(4) 0.060(5) 0.026(4) 0.003(3) -0.006(3) -0.018(4) O5 0.038(4) 0.016(3) 0.030(4) 0.006(3) 0.013(3) 0.003(3) O6 0.047(5) 0.027(4) 0.035(4) 0.009(3) 0.021(3) 0.017(3) O7 0.034(4) 0.015(3) 0.052(5) 0.000(3) 0.022(3) -0.001(3) O8 0.028(4) 0.015(3) 0.025(3) -0.003(3) 0.005(3) -0.004(3) O10 0.025(4) 0.043(5) 0.091(7) -0.028(5) -0.003(4) 0.002(3) O11 0.044(5) 0.053(5) 0.029(4) 0.014(4) 0.010(3) 0.024(4) O12 0.053(6) 0.095(9) 0.099(8) -0.053(7) 0.019(6) 0.009(6) N1 0.021(4) 0.023(4) 0.021(4) 0.004(3) 0.002(3) -0.003(3) N2 0.021(4) 0.029(4) 0.025(4) 0.000(3) -0.001(3) -0.011(3) N3 0.027(4) 0.020(4) 0.016(3) -0.003(3) 0.009(3) 0.001(3) N4 0.039(5) 0.015(4) 0.021(4) 0.003(3) 0.017(3) -0.002(3) C1 0.019(4) 0.015(4) 0.014(4) -0.001(3) 0.002(3) 0.000(3) C2 0.016(4) 0.024(5) 0.020(4) -0.002(4) 0.003(3) -0.003(4) C3 0.017(4) 0.028(5) 0.022(4) 0.003(4) 0.002(3) -0.002(4) C4 0.020(4) 0.012(4) 0.014(4) -0.001(3) 0.001(3) 0.002(3) C5 0.016(5) 0.033(6) 0.019(5) -0.005(4) 0.006(4) 0.002(4) C6 0.032(6) 0.033(6) 0.039(6) 0.009(5) 0.003(5) -0.009(5) C7 0.060(9) 0.058(9) 0.077(10) 0.000(8) 0.040(8) -0.019(7) C8 0.053(9) 0.065(10) 0.088(11) 0.021(9) 0.037(8) -0.009(7) C9 0.029(5) 0.014(4) 0.010(4) -0.004(3) 0.004(3) 0.003(3) C10 0.023(5) 0.016(5) 0.034(5) -0.003(4) 0.007(4) -0.002(4) C11 0.033(6) 0.020(5) 0.030(5) 0.003(4) 0.010(4) 0.001(4) C12 0.023(5) 0.015(4) 0.017(4) 0.004(3) 0.002(3) 0.009(3) C13 0.024(5) 0.018(5) 0.019(4) -0.010(4) 0.004(4) 0.000(4) C14 0.031(5) 0.029(5) 0.024(5) -0.002(4) 0.015(4) 0.001(4) C15 0.033(6) 0.042(6) 0.023(5) 0.008(5) 0.007(4) -0.002(5) C16 0.042(7) 0.049(7) 0.042(6) -0.015(6) 0.017(5) -0.010(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 C17 O9 1.204(9) . ? C17 O9 1.204(9) 5_566 ? C17 H17A 0.9603 . ? C17 H17B 0.9603 . ? O9 Eu2 2.395(14) . ? C17' O9' 1.175(8) . ? C17' O9' 1.175(8) 5_566 ? C17' H17A 0.9603 . ? C17' H17B 0.9603 . ? O9' Eu2 2.425(11) . ? O9' H17A 1.3018 . ? Eu1 O3 2.319(6) 6 ? Eu1 O2 2.352(6) 6 ? Eu1 O1 2.369(6) . ? Eu1 O8 2.390(6) 1_545 ? Eu1 O5 2.424(6) . ? Eu1 O10 2.468(8) . ? Eu1 N3 2.583(8) . ? Eu1 N1 2.612(7) . ? Eu2 O6 2.321(7) 2_556 ? Eu2 O6 2.321(7) . ? Eu2 O9 2.395(14) 2_556 ? Eu2 O7 2.404(6) 2_556 ? Eu2 O7 2.404(6) . ? Eu2 O9' 2.425(11) 2_556 ? Eu2 O11 2.427(7) 2_556 ? Eu2 O11 2.427(7) . ? O1 C4 1.273(9) . ? O2 C4 1.233(10) . ? O2 Eu1 2.352(6) 6_556 ? O3 C5 1.257(11) . ? O3 Eu1 2.319(6) 6_556 ? O4 C5 1.227(11) . ? O5 C12 1.258(11) . ? O6 C12 1.236(11) . ? O7 C13 1.249(11) . ? O8 C13 1.246(11) . ? O8 Eu1 2.390(6) 1_565 ? O10 O12 2.704(12) . ? O10 H1W 0.8499 . ? O10 H2W 0.8491 . ? O11 H3W 0.8504 . ? O11 H4W 0.8492 . ? O12 H5W 0.8499 . ? O12 H6W 0.8494 . ? N1 C3 1.321(12) . ? N1 C1 1.391(11) . ? N2 C3 1.355(11) . ? N2 C2 1.382(11) . ? N2 H2 0.8600 . ? N3 C11 1.325(12) . ? N3 C9 1.394(11) . ? N4 C11 1.348(12) . ? N4 C10 1.367(12) . ? N4 H4 0.8600 . ? C1 C2 1.376(12) . ? C1 C4 1.495(12) . ? C2 C5 1.514(12) . ? C3 C6 1.499(13) . ? C6 C7 1.464(17) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.510(17) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.387(12) . ? C9 C12 1.472(12) . ? C10 C13 1.498(12) . ? C11 C14 1.489(13) . ? C14 C15 1.519(13) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.504(14) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 O9 C17 O9 180.0(9) . 5_566 ? O9 C17 H17A 104.8 . . ? O9 C17 H17A 75.2 5_566 . ? O9 C17 H17B 75.1 . . ? O9 C17 H17B 104.9 5_566 . ? H17A C17 H17B 180.0 . . ? C17 O9 Eu2 152.0(18) . . ? C17 O9 H17B 44.1 . . ? Eu2 O9 H17B 153.4 . . ? O9' C17' O9' 180.000(3) . 5_566 ? O9' C17' H17A 74.4 . . ? O9' C17' H17A 105.6 5_566 . ? O9' C17' H17B 105.6 . . ? O9' C17' H17B 74.4 5_566 . ? H17A C17' H17B 180.0 . . ? C17' O9' Eu2 151.6(14) . . ? C17' O9' H17A 45.3 . . ? Eu2 O9' H17A 152.3 . . ? O3 Eu1 O2 75.7(2) 6 6 ? O3 Eu1 O1 104.2(2) 6 . ? O2 Eu1 O1 152.4(2) 6 . ? O3 Eu1 O8 79.0(2) 6 1_545 ? O2 Eu1 O8 75.9(2) 6 1_545 ? O1 Eu1 O8 77.1(2) . 1_545 ? O3 Eu1 O5 147.1(2) 6 . ? O2 Eu1 O5 122.2(2) 6 . ? O1 Eu1 O5 72.8(2) . . ? O8 Eu1 O5 129.6(2) 1_545 . ? O3 Eu1 O10 142.2(3) 6 . ? O2 Eu1 O10 73.7(3) 6 . ? O1 Eu1 O10 93.1(3) . . ? O8 Eu1 O10 72.4(2) 1_545 . ? O5 Eu1 O10 70.0(3) . . ? O3 Eu1 N3 100.0(2) 6 . ? O2 Eu1 N3 74.2(2) 6 . ? O1 Eu1 N3 131.6(2) . . ? O8 Eu1 N3 149.3(2) 1_545 . ? O5 Eu1 N3 64.4(2) . . ? O10 Eu1 N3 92.6(3) . . ? O3 Eu1 N1 75.0(2) 6 . ? O2 Eu1 N1 138.0(2) 6 . ? O1 Eu1 N1 65.1(2) . . ? O8 Eu1 N1 126.1(2) 1_545 . ? O5 Eu1 N1 74.3(2) . . ? O10 Eu1 N1 142.5(3) . . ? N3 Eu1 N1 82.1(2) . . ? O6 Eu2 O6 91.1(4) 2_556 . ? O6 Eu2 O9 77.1(6) 2_556 . ? O6 Eu2 O9 85.3(6) . . ? O6 Eu2 O9 85.3(6) 2_556 2_556 ? O6 Eu2 O9 77.1(6) . 2_556 ? O9 Eu2 O9 154.8(13) . 2_556 ? O6 Eu2 O7 76.9(2) 2_556 2_556 ? O6 Eu2 O7 145.5(2) . 2_556 ? O9 Eu2 O7 122.0(5) . 2_556 ? O9 Eu2 O7 69.9(5) 2_556 2_556 ? O6 Eu2 O7 145.5(2) 2_556 . ? O6 Eu2 O7 76.9(2) . . ? O9 Eu2 O7 69.9(5) . . ? O9 Eu2 O7 122.0(5) 2_556 . ? O7 Eu2 O7 129.5(3) 2_556 . ? O6 Eu2 O9' 69.5(4) 2_556 . ? O6 Eu2 O9' 73.1(5) . . ? O9 Eu2 O9' 14.9(5) . . ? O9 Eu2 O9' 140.0(11) 2_556 . ? O7 Eu2 O9' 129.2(4) 2_556 . ? O7 Eu2 O9' 76.0(4) . . ? O6 Eu2 O9' 73.1(5) 2_556 2_556 ? O6 Eu2 O9' 69.5(4) . 2_556 ? O9 Eu2 O9' 140.0(11) . 2_556 ? O9 Eu2 O9' 14.9(5) 2_556 2_556 ? O7 Eu2 O9' 76.0(4) 2_556 2_556 ? O7 Eu2 O9' 129.2(4) . 2_556 ? O9' Eu2 O9' 125.5(10) . 2_556 ? O6 Eu2 O11 147.4(2) 2_556 2_556 ? O6 Eu2 O11 99.1(3) . 2_556 ? O9 Eu2 O11 134.3(6) . 2_556 ? O9 Eu2 O11 67.3(6) 2_556 2_556 ? O7 Eu2 O11 77.3(3) 2_556 2_556 ? O7 Eu2 O11 67.0(2) . 2_556 ? O9' Eu2 O11 143.1(4) . 2_556 ? O9' Eu2 O11 81.7(5) 2_556 2_556 ? O6 Eu2 O11 99.1(3) 2_556 . ? O6 Eu2 O11 147.4(2) . . ? O9 Eu2 O11 67.3(6) . . ? O9 Eu2 O11 134.3(6) 2_556 . ? O7 Eu2 O11 67.0(2) 2_556 . ? O7 Eu2 O11 77.3(3) . . ? O9' Eu2 O11 81.7(5) . . ? O9' Eu2 O11 143.1(4) 2_556 . ? O11 Eu2 O11 88.7(4) 2_556 . ? C4 O1 Eu1 127.9(5) . . ? C4 O2 Eu1 149.9(6) . 6_556 ? C5 O3 Eu1 150.2(6) . 6_556 ? C12 O5 Eu1 127.0(5) . . ? C12 O6 Eu2 143.7(6) . . ? C13 O7 Eu2 148.9(6) . . ? C13 O8 Eu1 136.5(5) . 1_565 ? Eu1 O10 O12 135.8(4) . . ? Eu1 O10 H1W 119.8 . . ? O12 O10 H1W 88.7 . . ? Eu1 O10 H2W 140.8 . . ? O12 O10 H2W 7.8 . . ? H1W O10 H2W 80.9 . . ? Eu2 O11 H3W 133.7 . . ? Eu2 O11 H4W 119.3 . . ? H3W O11 H4W 101.7 . . ? O10 O12 H5W 101.2 . . ? O10 O12 H6W 129.5 . . ? H5W O12 H6W 95.7 . . ? C3 N1 C1 106.5(7) . . ? C3 N1 Eu1 139.0(6) . . ? C1 N1 Eu1 113.6(5) . . ? C3 N2 C2 109.2(7) . . ? C3 N2 H2 125.4 . . ? C2 N2 H2 125.4 . . ? C11 N3 C9 106.3(8) . . ? C11 N3 Eu1 138.7(6) . . ? C9 N3 Eu1 115.0(5) . . ? C11 N4 C10 109.8(8) . . ? C11 N4 H4 125.1 . . ? C10 N4 H4 125.1 . . ? C2 C1 N1 109.8(8) . . ? C2 C1 C4 132.7(8) . . ? N1 C1 C4 117.4(7) . . ? C1 C2 N2 104.5(7) . . ? C1 C2 C5 137.9(8) . . ? N2 C2 C5 117.4(8) . . ? N1 C3 N2 110.1(8) . . ? N1 C3 C6 127.9(8) . . ? N2 C3 C6 122.1(8) . . ? O2 C4 O1 123.0(8) . . ? O2 C4 C1 121.5(7) . . ? O1 C4 C1 115.5(7) . . ? O4 C5 O3 127.3(9) . . ? O4 C5 C2 116.2(8) . . ? O3 C5 C2 116.5(8) . . ? C7 C6 C3 114.0(10) . . ? C7 C6 H6A 108.8 . . ? C3 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C3 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 C8 112.7(12) . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N3 109.2(8) . . ? C10 C9 C12 133.1(8) . . ? N3 C9 C12 117.7(7) . . ? N4 C10 C9 104.6(8) . . ? N4 C10 C13 118.6(8) . . ? C9 C10 C13 136.5(9) . . ? N3 C11 N4 110.0(8) . . ? N3 C11 C14 126.0(9) . . ? N4 C11 C14 124.0(9) . . ? O6 C12 O5 122.3(8) . . ? O6 C12 C9 121.8(8) . . ? O5 C12 C9 115.8(7) . . ? O8 C13 O7 125.4(8) . . ? O8 C13 C10 114.7(8) . . ? O7 C13 C10 119.9(8) . . ? C11 C14 C15 113.1(9) . . ? C11 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C11 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 111.8(9) . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O9 C17 O9 Eu2 45(100) 5_566 . . . ? O9' C17' O9' Eu2 144(100) 5_566 . . . ? C17 O9 Eu2 O6 -94(3) . . . 2_556 ? C17 O9 Eu2 O6 -2(3) . . . . ? C17 O9 Eu2 O9 -47(3) . . . 2_556 ? C17 O9 Eu2 O7 -159(3) . . . 2_556 ? C17 O9 Eu2 O7 76(3) . . . . ? C17 O9 Eu2 O9' -36(3) . . . . ? C17 O9 Eu2 O9' -52(4) . . . 2_556 ? C17 O9 Eu2 O11 96(4) . . . 2_556 ? C17 O9 Eu2 O11 160(4) . . . . ? C17' O9' Eu2 O6 155(3) . . . 2_556 ? C17' O9' Eu2 O6 -107(3) . . . . ? C17' O9' Eu2 O9 37(2) . . . . ? C17' O9' Eu2 O9 -151(2) . . . 2_556 ? C17' O9' Eu2 O7 103(2) . . . 2_556 ? C17' O9' Eu2 O7 -27(2) . . . . ? C17' O9' Eu2 O9' -155(3) . . . 2_556 ? C17' O9' Eu2 O11 -25(3) . . . 2_556 ? C17' O9' Eu2 O11 52(3) . . . . ? O3 Eu1 O1 C4 67.6(7) 6 . . . ? O2 Eu1 O1 C4 154.0(6) 6 . . . ? O8 Eu1 O1 C4 142.6(7) 1_545 . . . ? O5 Eu1 O1 C4 -78.3(7) . . . . ? O10 Eu1 O1 C4 -146.3(7) . . . . ? N3 Eu1 O1 C4 -50.1(8) . . . . ? N1 Eu1 O1 C4 2.0(7) . . . . ? O3 Eu1 O5 C12 69.3(9) 6 . . . ? O2 Eu1 O5 C12 -46.7(8) 6 . . . ? O1 Eu1 O5 C12 158.9(8) . . . . ? O8 Eu1 O5 C12 -145.1(7) 1_545 . . . ? O10 Eu1 O5 C12 -101.1(8) . . . . ? N3 Eu1 O5 C12 2.1(7) . . . . ? N1 Eu1 O5 C12 90.7(8) . . . . ? O6 Eu2 O6 C12 89.3(12) 2_556 . . . ? O9 Eu2 O6 C12 12.4(13) . . . . ? O9 Eu2 O6 C12 174.2(13) 2_556 . . . ? O7 Eu2 O6 C12 157.5(10) 2_556 . . . ? O7 Eu2 O6 C12 -58.0(12) . . . . ? O9' Eu2 O6 C12 21.1(12) . . . . ? O9' Eu2 O6 C12 160.8(13) 2_556 . . . ? O11 Eu2 O6 C12 -121.7(12) 2_556 . . . ? O11 Eu2 O6 C12 -19.7(15) . . . . ? O6 Eu2 O7 C13 -50.5(15) 2_556 . . . ? O6 Eu2 O7 C13 21.9(13) . . . . ? O9 Eu2 O7 C13 -67.9(14) . . . . ? O9 Eu2 O7 C13 87.2(15) 2_556 . . . ? O7 Eu2 O7 C13 176.7(14) 2_556 . . . ? O9' Eu2 O7 C13 -53.7(14) . . . . ? O9' Eu2 O7 C13 71.1(15) 2_556 . . . ? O11 Eu2 O7 C13 127.9(14) 2_556 . . . ? O11 Eu2 O7 C13 -138.1(14) . . . . ? O3 Eu1 O10 O12 -170.1(6) 6 . . . ? O2 Eu1 O10 O12 -132.8(7) 6 . . . ? O1 Eu1 O10 O12 71.8(7) . . . . ? O8 Eu1 O10 O12 147.2(7) 1_545 . . . ? O5 Eu1 O10 O12 1.4(6) . . . . ? N3 Eu1 O10 O12 -60.1(7) . . . . ? N1 Eu1 O10 O12 20.2(10) . . . . ? O3 Eu1 N1 C3 55.5(10) 6 . . . ? O2 Eu1 N1 C3 8.3(12) 6 . . . ? O1 Eu1 N1 C3 169.3(10) . . . . ? O8 Eu1 N1 C3 119.4(10) 1_545 . . . ? O5 Eu1 N1 C3 -112.7(10) . . . . ? O10 Eu1 N1 C3 -131.0(9) . . . . ? N3 Eu1 N1 C3 -47.2(10) . . . . ? O3 Eu1 N1 C1 -111.1(6) 6 . . . ? O2 Eu1 N1 C1 -158.3(5) 6 . . . ? O1 Eu1 N1 C1 2.7(5) . . . . ? O8 Eu1 N1 C1 -47.3(7) 1_545 . . . ? O5 Eu1 N1 C1 80.7(6) . . . . ? O10 Eu1 N1 C1 62.4(8) . . . . ? N3 Eu1 N1 C1 146.2(6) . . . . ? O3 Eu1 N3 C11 30.3(10) 6 . . . ? O2 Eu1 N3 C11 -41.6(10) 6 . . . ? O1 Eu1 N3 C11 149.7(9) . . . . ? O8 Eu1 N3 C11 -55.0(12) 1_545 . . . ? O5 Eu1 N3 C11 179.8(11) . . . . ? O10 Eu1 N3 C11 -113.8(10) . . . . ? N1 Eu1 N3 C11 103.5(10) . . . . ? O3 Eu1 N3 C9 -151.9(6) 6 . . . ? O2 Eu1 N3 C9 136.2(6) 6 . . . ? O1 Eu1 N3 C9 -32.5(7) . . . . ? O8 Eu1 N3 C9 122.8(6) 1_545 . . . ? O5 Eu1 N3 C9 -2.4(6) . . . . ? O10 Eu1 N3 C9 64.0(6) . . . . ? N1 Eu1 N3 C9 -78.8(6) . . . . ? C3 N1 C1 C2 -1.6(10) . . . . ? Eu1 N1 C1 C2 169.3(6) . . . . ? C3 N1 C1 C4 -177.4(8) . . . . ? Eu1 N1 C1 C4 -6.5(9) . . . . ? N1 C1 C2 N2 1.0(10) . . . . ? C4 C1 C2 N2 175.9(9) . . . . ? N1 C1 C2 C5 -172.9(10) . . . . ? C4 C1 C2 C5 2.0(18) . . . . ? C3 N2 C2 C1 -0.1(10) . . . . ? C3 N2 C2 C5 175.3(8) . . . . ? C1 N1 C3 N2 1.5(10) . . . . ? Eu1 N1 C3 N2 -165.7(7) . . . . ? C1 N1 C3 C6 -178.1(9) . . . . ? Eu1 N1 C3 C6 14.6(17) . . . . ? C2 N2 C3 N1 -0.9(11) . . . . ? C2 N2 C3 C6 178.8(9) . . . . ? Eu1 O2 C4 O1 -161.7(8) 6_556 . . . ? Eu1 O2 C4 C1 19.7(17) 6_556 . . . ? Eu1 O1 C4 O2 175.4(6) . . . . ? Eu1 O1 C4 C1 -6.0(11) . . . . ? C2 C1 C4 O2 12.2(15) . . . . ? N1 C1 C4 O2 -173.1(8) . . . . ? C2 C1 C4 O1 -166.5(9) . . . . ? N1 C1 C4 O1 8.2(11) . . . . ? Eu1 O3 C5 O4 144.2(10) 6_556 . . . ? Eu1 O3 C5 C2 -36.0(17) 6_556 . . . ? C1 C2 C5 O4 170.0(11) . . . . ? N2 C2 C5 O4 -3.3(13) . . . . ? C1 C2 C5 O3 -9.8(16) . . . . ? N2 C2 C5 O3 176.9(8) . . . . ? N1 C3 C6 C7 -89.7(14) . . . . ? N2 C3 C6 C7 90.7(13) . . . . ? C3 C6 C7 C8 -169.6(12) . . . . ? C11 N3 C9 C10 -0.4(11) . . . . ? Eu1 N3 C9 C10 -178.8(6) . . . . ? C11 N3 C9 C12 -178.6(8) . . . . ? Eu1 N3 C9 C12 2.9(10) . . . . ? C11 N4 C10 C9 0.2(11) . . . . ? C11 N4 C10 C13 174.5(9) . . . . ? N3 C9 C10 N4 0.1(11) . . . . ? C12 C9 C10 N4 178.0(10) . . . . ? N3 C9 C10 C13 -172.7(11) . . . . ? C12 C9 C10 C13 5(2) . . . . ? C9 N3 C11 N4 0.5(11) . . . . ? Eu1 N3 C11 N4 178.4(7) . . . . ? C9 N3 C11 C14 -179.6(10) . . . . ? Eu1 N3 C11 C14 -1.7(17) . . . . ? C10 N4 C11 N3 -0.4(12) . . . . ? C10 N4 C11 C14 179.7(10) . . . . ? Eu2 O6 C12 O5 -132.1(9) . . . . ? Eu2 O6 C12 C9 51.1(16) . . . . ? Eu1 O5 C12 O6 -178.3(7) . . . . ? Eu1 O5 C12 C9 -1.3(12) . . . . ? C10 C9 C12 O6 -2.1(17) . . . . ? N3 C9 C12 O6 175.7(9) . . . . ? C10 C9 C12 O5 -179.1(10) . . . . ? N3 C9 C12 O5 -1.3(13) . . . . ? Eu1 O8 C13 O7 23.4(15) 1_565 . . . ? Eu1 O8 C13 C10 -157.7(6) 1_565 . . . ? Eu2 O7 C13 O8 -176.1(8) . . . . ? Eu2 O7 C13 C10 5.0(19) . . . . ? N4 C10 C13 O8 -14.8(13) . . . . ? C9 C10 C13 O8 157.2(11) . . . . ? N4 C10 C13 O7 164.2(9) . . . . ? C9 C10 C13 O7 -23.8(18) . . . . ? N3 C11 C14 C15 112.7(12) . . . . ? N4 C11 C14 C15 -67.4(14) . . . . ? C11 C14 C15 C16 -171.3(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O4 0.86 2.14 2.930(10) 152.8 7_557 O12 H6W O5 0.85 2.14 2.971(12) 164.5 2_556 O12 H5W O9' 0.85 2.25 3.10(2) 179.3 . O11 H3W O2 0.85 2.60 3.041(10) 113.9 2_566 O11 H4W O1 0.85 2.03 2.866(10) 168.1 2_566 O11 H3W O2 0.85 2.60 3.041(10) 113.9 2_566 O11 H3W O10 0.85 2.38 3.165(12) 153.7 5_566 O10 H2W O12 0.85 1.87 2.704(12) 168.7 . O10 H1W O7 0.85 2.53 3.160(12) 131.4 1_545 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.634 _refine_diff_density_min -1.750 _refine_diff_density_rms 0.265 # Attachment '- 3gd.cif' data_3gd _database_code_depnum_ccdc_archive 'CCDC 765404' #TrackingRef '- 3gd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H45 Gd3 N8 O24' _chemical_formula_weight 1409.52 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' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 35.058(3) _cell_length_b 9.2135(8) _cell_length_c 13.2650(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.8870(10) _cell_angle_gamma 90.00 _cell_volume 4269.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8021 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.22 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2732 _exptl_absorpt_coefficient_mu 4.708 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2896 _exptl_absorpt_correction_T_max 0.4683 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15818 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3975 _reflns_number_gt 3650 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+11.8699P] 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 3975 _refine_ls_number_parameters 327 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0213 _refine_ls_wR_factor_ref 0.0536 _refine_ls_wR_factor_gt 0.0521 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.028 _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 C17 C 0.0000 0.5000 0.5000 0.0392(9) Uani 0.412(12) 2 d SPDU . 1 H17A H 0.0064 0.4042 0.5244 0.047 Uiso 0.206(6) 1 d PR . 1 O9 O -0.0084(2) 0.5672(13) 0.5723(6) 0.0386(9) Uani 0.412(12) 1 d PDU . 1 C17' C 0.0000 0.5000 0.5000 0.0393(9) Uani 0.588(12) 2 d SPDU . 2 H17B H -0.0064 0.5958 0.4756 0.047 Uiso 0.294(6) 1 d PR . 2 O9' O -0.00439(17) 0.5046(10) 0.5841(4) 0.0384(9) Uani 0.588(12) 1 d PDU . 2 Gd1 Gd 0.109557(5) 0.069438(17) 0.629505(12) 0.01406(6) Uani 1 1 d . . . Gd2 Gd 0.0000 0.62184(3) 0.7500 0.01807(7) Uani 1 2 d S . . O1 O 0.09996(7) -0.0412(3) 0.78656(17) 0.0206(5) Uani 1 1 d . . . O2 O 0.10764(8) -0.0680(3) 0.95223(18) 0.0243(6) Uani 1 1 d . . . O3 O 0.17046(7) 0.0032(3) 1.09689(18) 0.0249(6) Uani 1 1 d . . . O4 O 0.22329(8) 0.1343(3) 1.0849(2) 0.0378(7) Uani 1 1 d . . . O5 O 0.07103(7) 0.2343(3) 0.72091(19) 0.0264(6) Uani 1 1 d . . . O6 O 0.04731(9) 0.4478(3) 0.7582(2) 0.0343(7) Uani 1 1 d . . . O7 O 0.04955(8) 0.7326(3) 0.6619(2) 0.0317(6) Uani 1 1 d . . . O8 O 0.09841(7) 0.8205(3) 0.58508(19) 0.0245(6) Uani 1 1 d . . . O10 O 0.04189(8) 0.0466(4) 0.5672(3) 0.0539(10) Uani 1 1 d . . . H1W H 0.0307 -0.0351 0.5696 0.081 Uiso 1 1 d R . . H2W H 0.0198 0.0756 0.5802 0.081 Uiso 1 1 d R . . O11 O -0.03420(9) 0.8085(4) 0.6513(2) 0.0437(8) Uani 1 1 d . . . H3W H -0.0404 0.8201 0.5884 0.066 Uiso 1 1 d R . . H4W H -0.0517 0.8561 0.6774 0.066 Uiso 1 1 d R . . O12 O -0.02474(11) 0.1744(5) 0.6069(3) 0.0784(13) Uani 1 1 d . . . H5W H -0.0191 0.2635 0.6009 0.118 Uiso 1 1 d R . . H6W H -0.0345 0.1837 0.6630 0.118 Uiso 1 1 d R . . N1 N 0.15434(8) 0.1635(3) 0.7815(2) 0.0209(6) Uani 1 1 d . . . N2 N 0.20067(9) 0.2272(3) 0.8952(2) 0.0251(7) Uani 1 1 d . . . H2 H 0.2211 0.2691 0.9214 0.030 Uiso 1 1 calc R . . N3 N 0.11229(9) 0.3379(3) 0.5759(2) 0.0204(6) Uani 1 1 d . . . N4 N 0.11841(10) 0.5591(3) 0.5176(2) 0.0266(7) Uani 1 1 d . . . H4 H 0.1263 0.6299 0.4824 0.032 Uiso 1 1 calc R . . C1 C 0.14944(10) 0.0926(4) 0.8725(2) 0.0172(7) Uani 1 1 d . . . C2 C 0.17858(10) 0.1321(4) 0.9446(3) 0.0193(7) Uani 1 1 d . . . C3 C 0.18542(11) 0.2446(4) 0.7991(3) 0.0245(8) Uani 1 1 d . . . C4 C 0.11700(10) -0.0113(4) 0.8729(2) 0.0162(7) Uani 1 1 d . . . C5 C 0.19186(10) 0.0868(4) 1.0510(3) 0.0210(8) Uani 1 1 d . . . C6 C 0.20283(12) 0.3445(5) 0.7276(3) 0.0369(10) Uani 1 1 d . . . H6A H 0.2151 0.4239 0.7659 0.044 Uiso 1 1 calc R . . H6B H 0.1825 0.3854 0.6820 0.044 Uiso 1 1 calc R . . C7 C 0.23143(17) 0.2761(6) 0.6663(5) 0.0631(16) Uani 1 1 d . . . H7A H 0.2186 0.2101 0.6176 0.076 Uiso 1 1 calc R . . H7B H 0.2495 0.2202 0.7102 0.076 Uiso 1 1 calc R . . C8 C 0.25309(18) 0.3909(7) 0.6105(5) 0.0760(19) Uani 1 1 d . . . H8A H 0.2352 0.4468 0.5674 0.114 Uiso 1 1 calc R . . H8B H 0.2710 0.3441 0.5702 0.114 Uiso 1 1 calc R . . H8C H 0.2666 0.4540 0.6588 0.114 Uiso 1 1 calc R . . C9 C 0.08899(10) 0.4317(4) 0.6257(3) 0.0194(7) Uani 1 1 d . . . C10 C 0.09250(11) 0.5703(4) 0.5900(3) 0.0216(8) Uani 1 1 d . . . C11 C 0.12949(11) 0.4186(4) 0.5108(3) 0.0242(8) Uani 1 1 d . . . C12 C 0.06724(10) 0.3678(4) 0.7069(3) 0.0202(8) Uani 1 1 d . . . C13 C 0.07865(11) 0.7183(4) 0.6150(3) 0.0214(8) Uani 1 1 d . . . C14 C 0.15725(12) 0.3674(4) 0.4392(3) 0.0283(9) Uani 1 1 d . . . H14A H 0.1640 0.2673 0.4546 0.034 Uiso 1 1 calc R . . H14B H 0.1804 0.4252 0.4487 0.034 Uiso 1 1 calc R . . C15 C 0.14124(13) 0.3779(5) 0.3291(3) 0.0353(10) Uani 1 1 d . . . H15A H 0.1384 0.4792 0.3101 0.042 Uiso 1 1 calc R . . H15B H 0.1161 0.3329 0.3213 0.042 Uiso 1 1 calc R . . C16 C 0.16771(14) 0.3028(5) 0.2595(3) 0.0439(11) Uani 1 1 d . . . H16A H 0.1930 0.3426 0.2708 0.066 Uiso 1 1 calc R . . H16B H 0.1582 0.3180 0.1903 0.066 Uiso 1 1 calc R . . H16C H 0.1685 0.2007 0.2738 0.066 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 C17 0.0394(11) 0.0404(11) 0.0378(10) -0.0014(6) 0.0036(6) 0.0002(7) O9 0.0390(10) 0.0398(11) 0.0371(10) -0.0012(6) 0.0038(6) 0.0001(7) C17' 0.0396(10) 0.0406(11) 0.0377(10) -0.0014(6) 0.0036(6) 0.0002(7) O9' 0.0389(10) 0.0397(11) 0.0368(10) -0.0012(6) 0.0040(6) 0.0000(6) Gd1 0.01827(10) 0.01243(10) 0.01163(10) 0.00054(6) 0.00213(7) 0.00079(6) Gd2 0.01933(13) 0.01671(13) 0.01862(13) 0.000 0.00430(10) 0.000 O1 0.0259(14) 0.0201(13) 0.0153(12) 0.0012(10) -0.0016(10) -0.0060(10) O2 0.0330(15) 0.0249(14) 0.0152(13) 0.0009(10) 0.0037(11) -0.0103(11) O3 0.0213(13) 0.0319(15) 0.0218(13) 0.0081(11) 0.0036(11) -0.0018(11) O4 0.0278(16) 0.056(2) 0.0282(15) 0.0049(14) -0.0067(12) -0.0169(14) O5 0.0328(15) 0.0163(13) 0.0320(14) 0.0030(11) 0.0131(12) 0.0044(11) O6 0.0438(18) 0.0276(15) 0.0344(16) 0.0073(12) 0.0207(14) 0.0155(13) O7 0.0327(16) 0.0175(14) 0.0473(17) -0.0039(12) 0.0183(14) -0.0024(11) O8 0.0318(15) 0.0145(13) 0.0282(14) -0.0010(10) 0.0092(12) -0.0035(11) O10 0.0216(16) 0.0421(19) 0.097(3) -0.0312(19) -0.0013(17) 0.0026(13) O11 0.0410(18) 0.057(2) 0.0343(16) 0.0150(15) 0.0080(14) 0.0243(15) O12 0.055(3) 0.093(3) 0.089(3) -0.039(3) 0.017(2) 0.012(2) N1 0.0221(16) 0.0228(16) 0.0180(15) 0.0025(12) 0.0024(12) -0.0041(13) N2 0.0230(17) 0.0290(18) 0.0229(16) 0.0024(13) -0.0003(13) -0.0103(14) N3 0.0265(17) 0.0165(15) 0.0188(15) -0.0010(12) 0.0053(13) 0.0015(13) N4 0.037(2) 0.0169(16) 0.0280(17) 0.0008(13) 0.0161(15) -0.0024(13) C1 0.0221(18) 0.0167(17) 0.0133(16) -0.0005(13) 0.0050(14) 0.0010(14) C2 0.0226(19) 0.0177(18) 0.0180(17) -0.0024(14) 0.0048(14) -0.0006(14) C3 0.0230(19) 0.028(2) 0.0228(19) 0.0043(15) 0.0026(15) -0.0034(16) C4 0.0206(18) 0.0144(17) 0.0136(17) -0.0005(13) 0.0018(14) 0.0045(14) C5 0.0213(19) 0.0235(19) 0.0182(18) -0.0015(14) 0.0021(15) 0.0001(15) C6 0.033(2) 0.040(3) 0.037(2) 0.0132(19) -0.0008(19) -0.0100(19) C7 0.068(4) 0.055(3) 0.072(4) 0.002(3) 0.043(3) -0.007(3) C8 0.063(4) 0.085(5) 0.085(5) 0.019(4) 0.041(4) -0.018(3) C9 0.0220(19) 0.0189(19) 0.0175(18) -0.0038(13) 0.0025(14) 0.0028(14) C10 0.025(2) 0.0193(19) 0.0211(19) -0.0023(14) 0.0064(16) -0.0004(15) C11 0.032(2) 0.0155(18) 0.026(2) 0.0020(14) 0.0062(17) 0.0009(15) C12 0.0197(18) 0.022(2) 0.0189(18) 0.0003(14) 0.0017(14) 0.0047(14) C13 0.029(2) 0.0163(18) 0.0191(18) -0.0013(14) 0.0037(16) -0.0009(15) C14 0.033(2) 0.028(2) 0.026(2) 0.0008(16) 0.0120(17) 0.0014(17) C15 0.038(2) 0.038(2) 0.031(2) 0.0010(18) 0.0071(19) -0.0004(19) C16 0.046(3) 0.053(3) 0.035(2) -0.011(2) 0.012(2) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C17 O9 1.199(7) . ? C17 O9 1.199(7) 5_566 ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? O9 Gd2 2.404(7) . ? C17' O9' 1.140(5) 5_566 ? C17' O9' 1.140(5) . ? C17' H17A 0.9600 . ? C17' H17B 0.9600 . ? O9' Gd2 2.445(5) . ? Gd1 O3 2.313(2) 6 ? Gd1 O2 2.347(2) 6 ? Gd1 O1 2.369(2) . ? Gd1 O8 2.392(2) 1_545 ? Gd1 O5 2.425(2) . ? Gd1 O10 2.454(3) . ? Gd1 N3 2.578(3) . ? Gd1 N1 2.596(3) . ? Gd2 O6 2.303(3) 2_556 ? Gd2 O6 2.303(3) . ? Gd2 O7 2.402(3) . ? Gd2 O7 2.402(3) 2_556 ? Gd2 O9 2.404(7) 2_556 ? Gd2 O11 2.417(3) 2_556 ? Gd2 O11 2.417(3) . ? Gd2 O9' 2.445(5) 2_556 ? O1 C4 1.276(4) . ? O2 C4 1.244(4) . ? O2 Gd1 2.347(2) 6_556 ? O3 C5 1.267(4) . ? O3 Gd1 2.313(2) 6_556 ? O4 C5 1.234(4) . ? O5 C12 1.249(4) . ? O6 C12 1.255(4) . ? O7 C13 1.246(4) . ? O8 C13 1.253(4) . ? O8 Gd1 2.392(2) 1_565 ? O10 O12 2.707(5) . ? O10 H1W 0.8499 . ? O10 H2W 0.8497 . ? O11 H3W 0.8500 . ? O11 H4W 0.8499 . ? O12 H5W 0.8498 . ? O12 H6W 0.8500 . ? N1 C3 1.326(5) . ? N1 C1 1.397(4) . ? N2 C3 1.350(5) . ? N2 C2 1.372(4) . ? N2 H2 0.8600 . ? N3 C11 1.323(5) . ? N3 C9 1.394(4) . ? N4 C11 1.357(5) . ? N4 C10 1.381(5) . ? N4 H4 0.8600 . ? C1 C2 1.387(5) . ? C1 C4 1.487(5) . ? C2 C5 1.507(5) . ? C3 C6 1.489(5) . ? C6 C7 1.484(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.530(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.371(5) . ? C9 C12 1.492(5) . ? C10 C13 1.494(5) . ? C11 C14 1.493(5) . ? C14 C15 1.522(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.529(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 O9 C17 O9 180.0(4) . 5_566 ? O9 C17 H17A 105.7 . . ? O9 C17 H17A 74.3 5_566 . ? O9 C17 H17B 74.3 . . ? O9 C17 H17B 105.7 5_566 . ? H17A C17 H17B 180.0 . . ? C17 O9 Gd2 150.9(8) . . ? C17 O9 H17B 44.5 . . ? Gd2 O9 H17B 154.2 . . ? O9' C17' O9' 180.0(6) 5_566 . ? O9' C17' H17A 104.5 5_566 . ? O9' C17' H17A 75.5 . . ? O9' C17' H17B 75.5 5_566 . ? O9' C17' H17B 104.5 . . ? H17A C17' H17B 180.0 . . ? C17' O9' Gd2 153.4(6) . . ? C17' O9' H17A 45.9 . . ? Gd2 O9' H17A 150.1 . . ? O3 Gd1 O2 76.05(9) 6 6 ? O3 Gd1 O1 104.03(9) 6 . ? O2 Gd1 O1 152.21(8) 6 . ? O3 Gd1 O8 79.09(9) 6 1_545 ? O2 Gd1 O8 75.97(8) 6 1_545 ? O1 Gd1 O8 76.78(8) . 1_545 ? O3 Gd1 O5 146.82(9) 6 . ? O2 Gd1 O5 122.34(8) 6 . ? O1 Gd1 O5 72.73(8) . . ? O8 Gd1 O5 129.61(8) 1_545 . ? O3 Gd1 O10 142.52(10) 6 . ? O2 Gd1 O10 73.60(11) 6 . ? O1 Gd1 O10 93.08(11) . . ? O8 Gd1 O10 72.65(10) 1_545 . ? O5 Gd1 O10 70.03(10) . . ? O3 Gd1 N3 99.74(9) 6 . ? O2 Gd1 N3 74.19(9) 6 . ? O1 Gd1 N3 131.84(8) . . ? O8 Gd1 N3 149.46(9) 1_545 . ? O5 Gd1 N3 64.67(9) . . ? O10 Gd1 N3 92.69(11) . . ? O3 Gd1 N1 74.63(9) 6 . ? O2 Gd1 N1 138.04(9) 6 . ? O1 Gd1 N1 65.34(8) . . ? O8 Gd1 N1 125.92(9) 1_545 . ? O5 Gd1 N1 74.24(9) . . ? O10 Gd1 N1 142.51(10) . . ? N3 Gd1 N1 81.93(9) . . ? O6 Gd2 O6 91.74(15) 2_556 . ? O6 Gd2 O7 145.14(9) 2_556 . ? O6 Gd2 O7 76.76(9) . . ? O6 Gd2 O7 76.76(9) 2_556 2_556 ? O6 Gd2 O7 145.14(9) . 2_556 ? O7 Gd2 O7 129.74(12) . 2_556 ? O6 Gd2 O9 77.3(3) 2_556 . ? O6 Gd2 O9 85.9(3) . . ? O7 Gd2 O9 69.2(2) . . ? O7 Gd2 O9 122.2(2) 2_556 . ? O6 Gd2 O9 85.9(3) 2_556 2_556 ? O6 Gd2 O9 77.3(2) . 2_556 ? O7 Gd2 O9 122.2(2) . 2_556 ? O7 Gd2 O9 69.2(2) 2_556 2_556 ? O9 Gd2 O9 155.8(6) . 2_556 ? O6 Gd2 O11 147.45(10) 2_556 2_556 ? O6 Gd2 O11 98.50(11) . 2_556 ? O7 Gd2 O11 67.40(10) . 2_556 ? O7 Gd2 O11 77.29(10) 2_556 2_556 ? O9 Gd2 O11 134.0(3) . 2_556 ? O9 Gd2 O11 66.7(3) 2_556 2_556 ? O6 Gd2 O11 98.50(11) 2_556 . ? O6 Gd2 O11 147.45(10) . . ? O7 Gd2 O11 77.29(10) . . ? O7 Gd2 O11 67.40(10) 2_556 . ? O9 Gd2 O11 66.7(3) . . ? O9 Gd2 O11 134.0(3) 2_556 . ? O11 Gd2 O11 89.29(16) 2_556 . ? O6 Gd2 O9' 70.12(16) 2_556 . ? O6 Gd2 O9' 74.0(2) . . ? O7 Gd2 O9' 75.07(16) . . ? O7 Gd2 O9' 129.28(17) 2_556 . ? O9 Gd2 O9' 14.5(2) . . ? O9 Gd2 O9' 141.6(5) 2_556 . ? O11 Gd2 O9' 142.42(17) 2_556 . ? O11 Gd2 O9' 80.6(2) . . ? O6 Gd2 O9' 74.0(2) 2_556 2_556 ? O6 Gd2 O9' 70.12(16) . 2_556 ? O7 Gd2 O9' 129.28(17) . 2_556 ? O7 Gd2 O9' 75.07(16) 2_556 2_556 ? O9 Gd2 O9' 141.6(5) . 2_556 ? O9 Gd2 O9' 14.5(2) 2_556 2_556 ? O11 Gd2 O9' 80.6(2) 2_556 2_556 ? O11 Gd2 O9' 142.42(17) . 2_556 ? O9' Gd2 O9' 127.5(4) . 2_556 ? C4 O1 Gd1 127.3(2) . . ? C4 O2 Gd1 149.7(2) . 6_556 ? C5 O3 Gd1 149.3(2) . 6_556 ? C12 O5 Gd1 126.8(2) . . ? C12 O6 Gd2 144.6(3) . . ? C13 O7 Gd2 148.7(2) . . ? C13 O8 Gd1 136.5(2) . 1_565 ? Gd1 O10 O12 136.27(16) . . ? Gd1 O10 H1W 119.9 . . ? O12 O10 H1W 88.3 . . ? Gd1 O10 H2W 140.9 . . ? O12 O10 H2W 7.5 . . ? H1W O10 H2W 80.9 . . ? Gd2 O11 H3W 133.9 . . ? Gd2 O11 H4W 119.2 . . ? H3W O11 H4W 101.7 . . ? O10 O12 H5W 100.9 . . ? O10 O12 H6W 129.3 . . ? H5W O12 H6W 95.7 . . ? C3 N1 C1 105.7(3) . . ? C3 N1 Gd1 139.3(2) . . ? C1 N1 Gd1 113.9(2) . . ? C3 N2 C2 109.4(3) . . ? C3 N2 H2 125.3 . . ? C2 N2 H2 125.3 . . ? C11 N3 C9 106.2(3) . . ? C11 N3 Gd1 138.5(2) . . ? C9 N3 Gd1 115.3(2) . . ? C11 N4 C10 109.1(3) . . ? C11 N4 H4 125.5 . . ? C10 N4 H4 125.5 . . ? C2 C1 N1 109.6(3) . . ? C2 C1 C4 133.3(3) . . ? N1 C1 C4 117.0(3) . . ? N2 C2 C1 104.5(3) . . ? N2 C2 C5 118.8(3) . . ? C1 C2 C5 136.4(3) . . ? N1 C3 N2 110.7(3) . . ? N1 C3 C6 127.7(3) . . ? N2 C3 C6 121.6(3) . . ? O2 C4 O1 122.1(3) . . ? O2 C4 C1 122.0(3) . . ? O1 C4 C1 115.8(3) . . ? O4 C5 O3 126.0(3) . . ? O4 C5 C2 116.0(3) . . ? O3 C5 C2 118.0(3) . . ? C3 C6 C7 114.8(4) . . ? C3 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C3 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C8 111.0(5) . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N3 109.9(3) . . ? C10 C9 C12 133.1(3) . . ? N3 C9 C12 117.0(3) . . ? C9 C10 N4 104.7(3) . . ? C9 C10 C13 137.1(3) . . ? N4 C10 C13 117.9(3) . . ? N3 C11 N4 110.1(3) . . ? N3 C11 C14 126.6(3) . . ? N4 C11 C14 123.3(3) . . ? O5 C12 O6 123.7(3) . . ? O5 C12 C9 116.2(3) . . ? O6 C12 C9 120.1(3) . . ? O7 C13 O8 125.2(3) . . ? O7 C13 C10 120.1(3) . . ? O8 C13 C10 114.6(3) . . ? C11 C14 C15 112.5(3) . . ? C11 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C11 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C14 C15 C16 110.9(4) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.0 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O9 C17 O9 Gd2 -47(2) 5_566 . . . ? O9' C17' O9' Gd2 65(2) 5_566 . . . ? C17 O9 Gd2 O6 -92.5(15) . . . 2_556 ? C17 O9 Gd2 O6 0.2(14) . . . . ? C17 O9 Gd2 O7 77.6(14) . . . . ? C17 O9 Gd2 O7 -157.7(13) . . . 2_556 ? C17 O9 Gd2 O9 -45.4(14) . . . 2_556 ? C17 O9 Gd2 O11 98.1(15) . . . 2_556 ? C17 O9 Gd2 O11 162.3(15) . . . . ? C17 O9 Gd2 O9' -33.9(11) . . . . ? C17 O9 Gd2 O9' -50.0(17) . . . 2_556 ? C17' O9' Gd2 O6 157.3(13) . . . 2_556 ? C17' O9' Gd2 O6 -104.8(12) . . . . ? C17' O9' Gd2 O7 -24.6(11) . . . . ? C17' O9' Gd2 O7 105.0(11) . . . 2_556 ? C17' O9' Gd2 O9 39.6(12) . . . . ? C17' O9' Gd2 O9 -148.0(11) . . . 2_556 ? C17' O9' Gd2 O11 -21.7(14) . . . 2_556 ? C17' O9' Gd2 O11 54.7(12) . . . . ? C17' O9' Gd2 O9' -153.0(12) . . . 2_556 ? O3 Gd1 O1 C4 68.3(3) 6 . . . ? O2 Gd1 O1 C4 155.0(2) 6 . . . ? O8 Gd1 O1 C4 143.3(3) 1_545 . . . ? O5 Gd1 O1 C4 -77.3(3) . . . . ? O10 Gd1 O1 C4 -145.3(3) . . . . ? N3 Gd1 O1 C4 -48.9(3) . . . . ? N1 Gd1 O1 C4 2.9(3) . . . . ? O3 Gd1 O5 C12 69.1(4) 6 . . . ? O2 Gd1 O5 C12 -47.5(3) 6 . . . ? O1 Gd1 O5 C12 158.4(3) . . . . ? O8 Gd1 O5 C12 -146.2(3) 1_545 . . . ? O10 Gd1 O5 C12 -101.6(3) . . . . ? N3 Gd1 O5 C12 1.5(3) . . . . ? N1 Gd1 O5 C12 89.9(3) . . . . ? O6 Gd2 O6 C12 87.3(5) 2_556 . . . ? O7 Gd2 O6 C12 -59.4(5) . . . . ? O7 Gd2 O6 C12 156.4(4) 2_556 . . . ? O9 Gd2 O6 C12 10.2(5) . . . . ? O9 Gd2 O6 C12 172.7(5) 2_556 . . . ? O11 Gd2 O6 C12 -123.7(5) 2_556 . . . ? O11 Gd2 O6 C12 -21.5(6) . . . . ? O9' Gd2 O6 C12 18.6(5) . . . . ? O9' Gd2 O6 C12 159.6(5) 2_556 . . . ? O6 Gd2 O7 C13 -52.4(6) 2_556 . . . ? O6 Gd2 O7 C13 21.2(5) . . . . ? O7 Gd2 O7 C13 175.4(5) 2_556 . . . ? O9 Gd2 O7 C13 -69.4(6) . . . . ? O9 Gd2 O7 C13 86.7(6) 2_556 . . . ? O11 Gd2 O7 C13 126.4(5) 2_556 . . . ? O11 Gd2 O7 C13 -139.0(5) . . . . ? O9' Gd2 O7 C13 -55.5(5) . . . . ? O9' Gd2 O7 C13 71.1(6) 2_556 . . . ? O3 Gd1 O10 O12 -169.9(2) 6 . . . ? O2 Gd1 O10 O12 -132.7(3) 6 . . . ? O1 Gd1 O10 O12 72.1(3) . . . . ? O8 Gd1 O10 O12 147.2(3) 1_545 . . . ? O5 Gd1 O10 O12 1.7(2) . . . . ? N3 Gd1 O10 O12 -60.1(3) . . . . ? N1 Gd1 O10 O12 20.2(4) . . . . ? O3 Gd1 N1 C3 54.9(4) 6 . . . ? O2 Gd1 N1 C3 7.7(4) 6 . . . ? O1 Gd1 N1 C3 168.7(4) . . . . ? O8 Gd1 N1 C3 118.7(4) 1_545 . . . ? O5 Gd1 N1 C3 -113.5(4) . . . . ? O10 Gd1 N1 C3 -131.4(4) . . . . ? N3 Gd1 N1 C3 -47.6(4) . . . . ? O3 Gd1 N1 C1 -111.1(2) 6 . . . ? O2 Gd1 N1 C1 -158.3(2) 6 . . . ? O1 Gd1 N1 C1 2.7(2) . . . . ? O8 Gd1 N1 C1 -47.3(3) 1_545 . . . ? O5 Gd1 N1 C1 80.6(2) . . . . ? O10 Gd1 N1 C1 62.6(3) . . . . ? N3 Gd1 N1 C1 146.4(2) . . . . ? O3 Gd1 N3 C11 30.0(4) 6 . . . ? O2 Gd1 N3 C11 -42.4(4) 6 . . . ? O1 Gd1 N3 C11 149.0(4) . . . . ? O8 Gd1 N3 C11 -55.0(5) 1_545 . . . ? O5 Gd1 N3 C11 179.1(4) . . . . ? O10 Gd1 N3 C11 -114.5(4) . . . . ? N1 Gd1 N3 C11 102.8(4) . . . . ? O3 Gd1 N3 C9 -151.5(2) 6 . . . ? O2 Gd1 N3 C9 136.1(3) 6 . . . ? O1 Gd1 N3 C9 -32.6(3) . . . . ? O8 Gd1 N3 C9 123.5(2) 1_545 . . . ? O5 Gd1 N3 C9 -2.4(2) . . . . ? O10 Gd1 N3 C9 64.0(3) . . . . ? N1 Gd1 N3 C9 -78.7(2) . . . . ? C3 N1 C1 C2 -0.7(4) . . . . ? Gd1 N1 C1 C2 169.9(2) . . . . ? C3 N1 C1 C4 -177.7(3) . . . . ? Gd1 N1 C1 C4 -7.1(4) . . . . ? C3 N2 C2 C1 0.5(4) . . . . ? C3 N2 C2 C5 175.2(3) . . . . ? N1 C1 C2 N2 0.1(4) . . . . ? C4 C1 C2 N2 176.5(4) . . . . ? N1 C1 C2 C5 -173.2(4) . . . . ? C4 C1 C2 C5 3.1(7) . . . . ? C1 N1 C3 N2 1.0(4) . . . . ? Gd1 N1 C3 N2 -165.7(3) . . . . ? C1 N1 C3 C6 -178.6(4) . . . . ? Gd1 N1 C3 C6 14.7(7) . . . . ? C2 N2 C3 N1 -0.9(4) . . . . ? C2 N2 C3 C6 178.7(4) . . . . ? Gd1 O2 C4 O1 -163.7(3) 6_556 . . . ? Gd1 O2 C4 C1 18.0(7) 6_556 . . . ? Gd1 O1 C4 O2 174.1(2) . . . . ? Gd1 O1 C4 C1 -7.6(4) . . . . ? C2 C1 C4 O2 11.8(6) . . . . ? N1 C1 C4 O2 -172.1(3) . . . . ? C2 C1 C4 O1 -166.6(4) . . . . ? N1 C1 C4 O1 9.5(4) . . . . ? Gd1 O3 C5 O4 145.1(4) 6_556 . . . ? Gd1 O3 C5 C2 -35.9(6) 6_556 . . . ? N2 C2 C5 O4 -3.5(5) . . . . ? C1 C2 C5 O4 169.2(4) . . . . ? N2 C2 C5 O3 177.5(3) . . . . ? C1 C2 C5 O3 -9.9(6) . . . . ? N1 C3 C6 C7 -89.3(6) . . . . ? N2 C3 C6 C7 91.1(5) . . . . ? C3 C6 C7 C8 -169.3(5) . . . . ? C11 N3 C9 C10 -0.3(4) . . . . ? Gd1 N3 C9 C10 -179.2(2) . . . . ? C11 N3 C9 C12 -177.8(3) . . . . ? Gd1 N3 C9 C12 3.2(4) . . . . ? N3 C9 C10 N4 0.0(4) . . . . ? C12 C9 C10 N4 177.0(4) . . . . ? N3 C9 C10 C13 -174.1(4) . . . . ? C12 C9 C10 C13 2.9(8) . . . . ? C11 N4 C10 C9 0.3(4) . . . . ? C11 N4 C10 C13 175.8(3) . . . . ? C9 N3 C11 N4 0.5(4) . . . . ? Gd1 N3 C11 N4 179.0(3) . . . . ? C9 N3 C11 C14 -179.7(4) . . . . ? Gd1 N3 C11 C14 -1.1(7) . . . . ? C10 N4 C11 N3 -0.5(5) . . . . ? C10 N4 C11 C14 179.6(4) . . . . ? Gd1 O5 C12 O6 -178.7(3) . . . . ? Gd1 O5 C12 C9 -0.4(5) . . . . ? Gd2 O6 C12 O5 -129.7(4) . . . . ? Gd2 O6 C12 C9 52.1(6) . . . . ? C10 C9 C12 O5 -178.9(4) . . . . ? N3 C9 C12 O5 -2.1(5) . . . . ? C10 C9 C12 O6 -0.5(7) . . . . ? N3 C9 C12 O6 176.3(3) . . . . ? Gd2 O7 C13 O8 -174.7(3) . . . . ? Gd2 O7 C13 C10 5.5(7) . . . . ? Gd1 O8 C13 O7 22.6(6) 1_565 . . . ? Gd1 O8 C13 C10 -157.5(3) 1_565 . . . ? C9 C10 C13 O7 -22.4(7) . . . . ? N4 C10 C13 O7 164.1(3) . . . . ? C9 C10 C13 O8 157.7(4) . . . . ? N4 C10 C13 O8 -15.8(5) . . . . ? N3 C11 C14 C15 112.4(4) . . . . ? N4 C11 C14 C15 -67.8(5) . . . . ? C11 C14 C15 C16 -171.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O4 0.86 2.15 2.947(4) 153.5 7_557 O12 H6W O5 0.85 2.14 2.964(5) 164.7 2_556 O12 H5W O9' 0.85 2.30 3.145(10) 179.5 . O11 H3W O2 0.85 2.59 3.034(4) 113.9 2_566 O11 H4W O1 0.85 2.03 2.870(4) 168.3 2_566 O11 H3W O2 0.85 2.59 3.034(4) 113.9 2_566 O11 H3W O10 0.85 2.40 3.181(5) 153.3 5_566 O10 H2W O12 0.85 1.87 2.707(5) 169.1 . O10 H1W O7 0.85 2.53 3.157(5) 131.8 1_545 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.930 _refine_diff_density_min -1.852 _refine_diff_density_rms 0.107 # Attachment '- 4.dy.cif' data_4dy _database_code_depnum_ccdc_archive 'CCDC 765405' #TrackingRef '- 4.dy.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H45 Dy3 N8 O24' _chemical_formula_weight 1425.27 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 C2/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 35.085(3) _cell_length_b 9.1620(9) _cell_length_c 13.1662(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.8570(10) _cell_angle_gamma 90.00 _cell_volume 4217.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8010 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2756 _exptl_absorpt_coefficient_mu 5.363 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2554 _exptl_absorpt_correction_T_max 0.4289 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15401 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3907 _reflns_number_gt 3596 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0169P)^2^+24.1772P] 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 3907 _refine_ls_number_parameters 327 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0526 _refine_ls_wR_factor_gt 0.0511 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.069 _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 C17 C 0.0000 0.5000 0.5000 0.0375(10) Uani 0.426(14) 2 d SPDU . 1 H17A H 0.0064 0.4042 0.5244 0.045 Uiso 0.213(7) 1 d PR . 1 O9 O -0.0075(3) 0.5662(15) 0.5739(7) 0.0370(10) Uani 0.426(14) 1 d PDU . 1 C17' C 0.0000 0.5000 0.5000 0.0375(10) Uani 0.574(14) 2 d SPDU . 2 H17B H -0.0064 0.5958 0.4756 0.045 Uiso 0.287(7) 1 d PR . 2 O9' O -0.0041(2) 0.5042(12) 0.5852(4) 0.0368(10) Uani 0.574(14) 1 d PDU . 2 Dy1 Dy 0.108991(5) 0.069889(19) 0.629772(13) 0.01402(6) Uani 1 1 d . . . Dy2 Dy 0.0000 0.62105(3) 0.7500 0.01657(7) Uani 1 2 d S . . O1 O 0.09938(8) -0.0409(3) 0.7860(2) 0.0194(6) Uani 1 1 d . . . O2 O 0.10687(9) -0.0694(3) 0.9531(2) 0.0217(6) Uani 1 1 d . . . O3 O 0.16938(8) 0.0017(3) 1.0988(2) 0.0235(6) Uani 1 1 d . . . O4 O 0.22258(9) 0.1317(4) 1.0861(2) 0.0340(8) Uani 1 1 d . . . O5 O 0.07085(9) 0.2326(3) 0.7219(2) 0.0240(7) Uani 1 1 d . . . O6 O 0.04648(10) 0.4465(3) 0.7581(2) 0.0314(8) Uani 1 1 d . . . O7 O 0.04891(9) 0.7327(3) 0.6622(2) 0.0299(7) Uani 1 1 d . . . O8 O 0.09795(8) 0.8219(3) 0.5856(2) 0.0220(6) Uani 1 1 d . . . O10 O 0.04242(10) 0.0481(4) 0.5672(3) 0.0494(11) Uani 1 1 d . . . H1W H 0.0313 -0.0336 0.5696 0.074 Uiso 1 1 d R . . H2W H 0.0204 0.0770 0.5802 0.074 Uiso 1 1 d R . . O11 O -0.03348(10) 0.8057(4) 0.6516(3) 0.0411(9) Uani 1 1 d . . . H3W H -0.0397 0.8172 0.5888 0.062 Uiso 1 1 d R . . H4W H -0.0509 0.8533 0.6777 0.062 Uiso 1 1 d R . . O12 O -0.02445(12) 0.1722(6) 0.6067(4) 0.0732(14) Uani 1 1 d . . . H5W H -0.0188 0.2613 0.6006 0.110 Uiso 1 1 d R . . H6W H -0.0342 0.1815 0.6628 0.110 Uiso 1 1 d R . . N1 N 0.15329(10) 0.1652(4) 0.7813(2) 0.0198(7) Uani 1 1 d . . . N2 N 0.19994(10) 0.2282(4) 0.8959(3) 0.0222(8) Uani 1 1 d . . . H2 H 0.2203 0.2705 0.9224 0.027 Uiso 1 1 calc R . . N3 N 0.11167(10) 0.3374(4) 0.5763(2) 0.0183(7) Uani 1 1 d . . . N4 N 0.11795(10) 0.5588(4) 0.5171(3) 0.0221(8) Uani 1 1 d . . . H4 H 0.1259 0.6299 0.4818 0.026 Uiso 1 1 calc R . . C1 C 0.14861(11) 0.0929(4) 0.8732(3) 0.0162(8) Uani 1 1 d . . . C2 C 0.17759(12) 0.1315(4) 0.9454(3) 0.0181(8) Uani 1 1 d . . . C3 C 0.18462(12) 0.2456(5) 0.7991(3) 0.0214(9) Uani 1 1 d . . . C4 C 0.11628(11) -0.0111(4) 0.8726(3) 0.0159(8) Uani 1 1 d . . . C5 C 0.19099(12) 0.0857(5) 1.0524(3) 0.0201(9) Uani 1 1 d . . . C6 C 0.20216(13) 0.3463(5) 0.7268(4) 0.0304(11) Uani 1 1 d . . . H6A H 0.2142 0.4266 0.7653 0.036 Uiso 1 1 calc R . . H6B H 0.1820 0.3867 0.6803 0.036 Uiso 1 1 calc R . . C7 C 0.23129(17) 0.2763(6) 0.6657(5) 0.0501(16) Uani 1 1 d . . . H7A H 0.2186 0.2101 0.6162 0.060 Uiso 1 1 calc R . . H7B H 0.2491 0.2201 0.7105 0.060 Uiso 1 1 calc R . . C8 C 0.25312(18) 0.3919(7) 0.6106(5) 0.0586(17) Uani 1 1 d . . . H8A H 0.2354 0.4504 0.5686 0.088 Uiso 1 1 calc R . . H8B H 0.2706 0.3450 0.5686 0.088 Uiso 1 1 calc R . . H8C H 0.2672 0.4530 0.6597 0.088 Uiso 1 1 calc R . . C9 C 0.08844(12) 0.4311(4) 0.6259(3) 0.0165(8) Uani 1 1 d . . . C10 C 0.09192(12) 0.5701(4) 0.5895(3) 0.0199(9) Uani 1 1 d . . . C11 C 0.12910(12) 0.4174(4) 0.5104(3) 0.0202(9) Uani 1 1 d . . . C12 C 0.06656(12) 0.3667(4) 0.7071(3) 0.0185(9) Uani 1 1 d . . . C13 C 0.07811(12) 0.7194(4) 0.6154(3) 0.0186(9) Uani 1 1 d . . . C14 C 0.15683(13) 0.3666(5) 0.4389(3) 0.0240(9) Uani 1 1 d . . . H14A H 0.1637 0.2661 0.4547 0.029 Uiso 1 1 calc R . . H14B H 0.1799 0.4251 0.4487 0.029 Uiso 1 1 calc R . . C15 C 0.14102(14) 0.3764(5) 0.3274(3) 0.0300(10) Uani 1 1 d . . . H15A H 0.1160 0.3310 0.3195 0.036 Uiso 1 1 calc R . . H15B H 0.1381 0.4782 0.3081 0.036 Uiso 1 1 calc R . . C16 C 0.16726(15) 0.3013(6) 0.2573(4) 0.0358(12) Uani 1 1 d . . . H16A H 0.1925 0.3418 0.2682 0.054 Uiso 1 1 calc R . . H16B H 0.1576 0.3162 0.1876 0.054 Uiso 1 1 calc R . . H16C H 0.1682 0.1987 0.2718 0.054 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 C17 0.0375(11) 0.0385(12) 0.0365(11) -0.0012(6) 0.0034(6) 0.0002(7) O9 0.0371(11) 0.0380(12) 0.0359(11) -0.0009(6) 0.0037(6) 0.0001(7) C17' 0.0376(11) 0.0387(12) 0.0364(11) -0.0012(7) 0.0034(6) 0.0002(7) O9' 0.0370(11) 0.0379(12) 0.0357(11) -0.0011(6) 0.0037(6) 0.0001(7) Dy1 0.01786(11) 0.01215(10) 0.01224(10) 0.00086(7) 0.00236(7) 0.00093(7) Dy2 0.01735(15) 0.01488(14) 0.01802(14) 0.000 0.00456(11) 0.000 O1 0.0246(16) 0.0182(14) 0.0146(14) 0.0015(11) -0.0025(12) -0.0047(12) O2 0.0288(17) 0.0215(15) 0.0150(14) 0.0005(11) 0.0025(12) -0.0050(12) O3 0.0205(16) 0.0312(17) 0.0192(15) 0.0048(13) 0.0041(12) -0.0014(13) O4 0.0264(19) 0.050(2) 0.0244(17) 0.0045(15) -0.0043(14) -0.0145(16) O5 0.0296(18) 0.0148(15) 0.0298(16) 0.0023(12) 0.0152(13) 0.0045(13) O6 0.042(2) 0.0236(16) 0.0315(18) 0.0063(13) 0.0186(15) 0.0154(14) O7 0.0286(18) 0.0178(15) 0.0460(19) -0.0023(14) 0.0192(15) -0.0026(13) O8 0.0273(17) 0.0124(14) 0.0274(16) -0.0028(12) 0.0095(13) -0.0031(12) O10 0.0194(19) 0.038(2) 0.091(3) -0.029(2) 0.0020(19) 0.0017(15) O11 0.041(2) 0.053(2) 0.0305(18) 0.0147(16) 0.0072(16) 0.0257(18) O12 0.048(3) 0.091(4) 0.083(3) -0.041(3) 0.016(2) 0.008(2) N1 0.0207(19) 0.0206(18) 0.0186(17) 0.0019(14) 0.0045(14) -0.0017(15) N2 0.0196(19) 0.0261(19) 0.0207(18) 0.0025(15) 0.0008(15) -0.0071(15) N3 0.025(2) 0.0143(17) 0.0168(17) -0.0004(13) 0.0072(14) 0.0028(14) N4 0.031(2) 0.0135(17) 0.0241(19) 0.0021(14) 0.0141(16) -0.0029(15) C1 0.019(2) 0.0158(19) 0.0138(19) -0.0011(15) 0.0024(16) 0.0026(16) C2 0.019(2) 0.019(2) 0.017(2) -0.0006(16) 0.0052(16) 0.0003(16) C3 0.019(2) 0.023(2) 0.022(2) 0.0029(17) 0.0028(17) 0.0003(18) C4 0.021(2) 0.0103(18) 0.016(2) 0.0006(15) 0.0044(16) 0.0025(16) C5 0.018(2) 0.025(2) 0.017(2) -0.0015(17) 0.0024(17) 0.0006(17) C6 0.025(3) 0.035(3) 0.031(3) 0.009(2) 0.001(2) -0.005(2) C7 0.053(4) 0.040(3) 0.063(4) 0.003(3) 0.038(3) -0.006(3) C8 0.046(4) 0.068(4) 0.065(4) 0.013(3) 0.025(3) -0.017(3) C9 0.017(2) 0.0139(19) 0.018(2) -0.0010(15) 0.0003(16) 0.0029(16) C10 0.020(2) 0.020(2) 0.020(2) -0.0018(16) 0.0040(17) -0.0001(17) C11 0.022(2) 0.018(2) 0.021(2) -0.0006(16) 0.0038(18) 0.0001(17) C12 0.019(2) 0.018(2) 0.019(2) -0.0003(16) 0.0033(17) 0.0032(17) C13 0.020(2) 0.015(2) 0.020(2) -0.0020(16) 0.0015(17) 0.0004(16) C14 0.027(2) 0.020(2) 0.026(2) -0.0003(18) 0.0093(19) 0.0030(18) C15 0.031(3) 0.033(3) 0.027(2) -0.001(2) 0.005(2) -0.002(2) C16 0.039(3) 0.040(3) 0.029(3) -0.007(2) 0.008(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C17 O9 1.195(7) . ? C17 O9 1.195(7) 5_566 ? C17 H17A 0.9548 . ? C17 H17B 0.9547 . ? O9 Dy2 2.365(7) . ? C17' O9' 1.144(5) . ? C17' O9' 1.144(5) 5_566 ? C17' H17A 0.9548 . ? C17' H17B 0.9547 . ? O9' Dy2 2.413(6) . ? O9' H17A 1.2896 . ? Dy1 O3 2.287(3) 6 ? Dy1 O2 2.320(3) 6 ? Dy1 O1 2.344(3) . ? Dy1 O8 2.370(3) 1_545 ? Dy1 O5 2.399(3) . ? Dy1 O10 2.418(3) . ? Dy1 N3 2.554(3) . ? Dy1 N1 2.576(3) . ? Dy2 O6 2.280(3) . ? Dy2 O6 2.280(3) 2_556 ? Dy2 O9 2.365(7) 2_556 ? Dy2 O11 2.379(3) 2_556 ? Dy2 O11 2.379(3) . ? Dy2 O7 2.380(3) . ? Dy2 O7 2.380(3) 2_556 ? Dy2 O9' 2.413(6) 2_556 ? O1 C4 1.270(5) . ? O2 C4 1.256(5) . ? O2 Dy1 2.320(3) 6_556 ? O3 C5 1.272(5) . ? O3 Dy1 2.287(3) 6_556 ? O4 C5 1.233(5) . ? O5 C12 1.251(5) . ? O6 C12 1.249(5) . ? O7 C13 1.245(5) . ? O8 C13 1.252(5) . ? O8 Dy1 2.370(3) 1_565 ? O10 O12 2.697(5) . ? O10 H1W 0.8463 . ? O10 H2W 0.8494 . ? O11 H3W 0.8441 . ? O11 H4W 0.8477 . ? O12 H5W 0.8454 . ? O12 H6W 0.8449 . ? N1 C3 1.328(5) . ? N1 C1 1.401(5) . ? N2 C3 1.350(5) . ? N2 C2 1.383(5) . ? N2 H2 0.8600 . ? N3 C11 1.324(5) . ? N3 C9 1.386(5) . ? N4 C11 1.358(5) . ? N4 C10 1.379(5) . ? N4 H4 0.8600 . ? C1 C2 1.378(6) . ? C1 C4 1.481(6) . ? C2 C5 1.506(6) . ? C3 C6 1.494(6) . ? C6 C7 1.497(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.526(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.369(6) . ? C9 C12 1.489(5) . ? C10 C13 1.500(5) . ? C11 C14 1.485(6) . ? C14 C15 1.527(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.522(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 O9 C17 O9 180.0(9) . 5_566 ? O9 C17 H17A 104.7 . . ? O9 C17 H17A 75.3 5_566 . ? O9 C17 H17B 75.3 . . ? O9 C17 H17B 104.7 5_566 . ? H17A C17 H17B 180.0 . . ? C17 O9 Dy2 153.1(9) . . ? C17 O9 H17B 44.1 . . ? Dy2 O9 H17B 154.6 . . ? O9' C17' O9' 180.000(2) . 5_566 ? O9' C17' H17A 75.2 . . ? O9' C17' H17A 104.8 5_566 . ? O9' C17' H17B 104.8 . . ? O9' C17' H17B 75.2 5_566 . ? H17A C17' H17B 180.0 . . ? C17' O9' Dy2 153.4(7) . . ? C17' O9' H17A 45.7 . . ? Dy2 O9' H17A 151.1 . . ? O3 Dy1 O2 76.85(10) 6 6 ? O3 Dy1 O1 103.69(10) 6 . ? O2 Dy1 O1 152.12(10) 6 . ? O3 Dy1 O8 79.40(10) 6 1_545 ? O2 Dy1 O8 76.18(10) 6 1_545 ? O1 Dy1 O8 76.56(9) . 1_545 ? O3 Dy1 O5 146.39(10) 6 . ? O2 Dy1 O5 122.39(10) 6 . ? O1 Dy1 O5 72.41(10) . . ? O8 Dy1 O5 129.30(10) 1_545 . ? O3 Dy1 O10 142.96(11) 6 . ? O2 Dy1 O10 73.17(12) 6 . ? O1 Dy1 O10 93.24(13) . . ? O8 Dy1 O10 72.78(11) 1_545 . ? O5 Dy1 O10 70.09(11) . . ? O3 Dy1 N3 99.76(11) 6 . ? O2 Dy1 N3 74.00(10) 6 . ? O1 Dy1 N3 132.00(10) . . ? O8 Dy1 N3 149.49(10) 1_545 . ? O5 Dy1 N3 65.06(10) . . ? O10 Dy1 N3 92.44(12) . . ? O3 Dy1 N1 74.21(10) 6 . ? O2 Dy1 N1 138.00(10) 6 . ? O1 Dy1 N1 65.74(10) . . ? O8 Dy1 N1 126.21(10) 1_545 . ? O5 Dy1 N1 73.96(11) . . ? O10 Dy1 N1 142.55(12) . . ? N3 Dy1 N1 81.63(11) . . ? O6 Dy2 O6 90.91(17) . 2_556 ? O6 Dy2 O9 77.6(3) . 2_556 ? O6 Dy2 O9 85.2(3) 2_556 2_556 ? O6 Dy2 O9 85.2(3) . . ? O6 Dy2 O9 77.6(3) 2_556 . ? O9 Dy2 O9 155.5(7) 2_556 . ? O6 Dy2 O11 98.93(13) . 2_556 ? O6 Dy2 O11 147.38(11) 2_556 2_556 ? O9 Dy2 O11 66.9(3) 2_556 2_556 ? O9 Dy2 O11 133.9(3) . 2_556 ? O6 Dy2 O11 147.38(11) . . ? O6 Dy2 O11 98.93(13) 2_556 . ? O9 Dy2 O11 133.9(3) 2_556 . ? O9 Dy2 O11 66.9(3) . . ? O11 Dy2 O11 89.37(19) 2_556 . ? O6 Dy2 O7 77.41(11) . . ? O6 Dy2 O7 145.19(11) 2_556 . ? O9 Dy2 O7 122.8(3) 2_556 . ? O9 Dy2 O7 68.9(3) . . ? O11 Dy2 O7 67.41(11) 2_556 . ? O11 Dy2 O7 76.88(12) . . ? O6 Dy2 O7 145.19(11) . 2_556 ? O6 Dy2 O7 77.41(11) 2_556 2_556 ? O9 Dy2 O7 68.9(3) 2_556 2_556 ? O9 Dy2 O7 122.8(3) . 2_556 ? O11 Dy2 O7 76.88(12) 2_556 2_556 ? O11 Dy2 O7 67.41(11) . 2_556 ? O7 Dy2 O7 129.08(14) . 2_556 ? O6 Dy2 O9' 73.6(2) . . ? O6 Dy2 O9' 70.1(2) 2_556 . ? O9 Dy2 O9' 141.3(6) 2_556 . ? O9 Dy2 O9' 14.3(2) . . ? O11 Dy2 O9' 142.5(2) 2_556 . ? O11 Dy2 O9' 80.6(3) . . ? O7 Dy2 O9' 75.17(19) . . ? O7 Dy2 O9' 129.6(2) 2_556 . ? O6 Dy2 O9' 70.1(2) . 2_556 ? O6 Dy2 O9' 73.6(2) 2_556 2_556 ? O9 Dy2 O9' 14.3(2) 2_556 2_556 ? O9 Dy2 O9' 141.3(6) . 2_556 ? O11 Dy2 O9' 80.6(3) 2_556 2_556 ? O11 Dy2 O9' 142.5(2) . 2_556 ? O7 Dy2 O9' 129.6(2) . 2_556 ? O7 Dy2 O9' 75.17(19) 2_556 2_556 ? O9' Dy2 O9' 127.3(5) . 2_556 ? C4 O1 Dy1 127.2(2) . . ? C4 O2 Dy1 149.1(3) . 6_556 ? C5 O3 Dy1 149.1(3) . 6_556 ? C12 O5 Dy1 126.6(2) . . ? C12 O6 Dy2 145.0(3) . . ? C13 O7 Dy2 148.8(3) . . ? C13 O8 Dy1 136.6(3) . 1_565 ? Dy1 O10 O12 136.92(17) . . ? Dy1 O10 H1W 119.8 . . ? O12 O10 H1W 87.3 . . ? Dy1 O10 H2W 140.9 . . ? O12 O10 H2W 6.7 . . ? H1W O10 H2W 80.6 . . ? Dy2 O11 H3W 134.1 . . ? Dy2 O11 H4W 119.0 . . ? H3W O11 H4W 101.5 . . ? O10 O12 H5W 100.0 . . ? O10 O12 H6W 129.4 . . ? H5W O12 H6W 95.8 . . ? C3 N1 C1 105.4(3) . . ? C3 N1 Dy1 139.5(3) . . ? C1 N1 Dy1 113.7(2) . . ? C3 N2 C2 108.9(3) . . ? C3 N2 H2 125.5 . . ? C2 N2 H2 125.5 . . ? C11 N3 C9 106.7(3) . . ? C11 N3 Dy1 137.9(3) . . ? C9 N3 Dy1 115.3(2) . . ? C11 N4 C10 109.1(3) . . ? C11 N4 H4 125.5 . . ? C10 N4 H4 125.5 . . ? C2 C1 N1 109.9(3) . . ? C2 C1 C4 133.5(4) . . ? N1 C1 C4 116.4(3) . . ? C1 C2 N2 104.7(3) . . ? C1 C2 C5 136.6(4) . . ? N2 C2 C5 118.4(4) . . ? N1 C3 N2 111.0(4) . . ? N1 C3 C6 127.6(4) . . ? N2 C3 C6 121.4(4) . . ? O2 C4 O1 122.0(4) . . ? O2 C4 C1 121.7(3) . . ? O1 C4 C1 116.3(3) . . ? O4 C5 O3 126.0(4) . . ? O4 C5 C2 116.2(4) . . ? O3 C5 C2 117.8(4) . . ? C3 C6 C7 114.5(4) . . ? C3 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C3 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 110.6(5) . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N3 109.7(3) . . ? C10 C9 C12 133.3(4) . . ? N3 C9 C12 116.9(3) . . ? C9 C10 N4 104.9(3) . . ? C9 C10 C13 136.7(4) . . ? N4 C10 C13 118.1(3) . . ? N3 C11 N4 109.6(3) . . ? N3 C11 C14 127.2(4) . . ? N4 C11 C14 123.2(4) . . ? O6 C12 O5 123.8(4) . . ? O6 C12 C9 120.1(4) . . ? O5 C12 C9 116.0(3) . . ? O7 C13 O8 125.7(4) . . ? O7 C13 C10 119.8(4) . . ? O8 C13 C10 114.5(4) . . ? C11 C14 C15 112.8(4) . . ? C11 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C11 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 111.5(4) . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O9 C17 O9 Dy2 134(54) 5_566 . . . ? O9' C17' O9' Dy2 -130(100) 5_566 . . . ? C17 O9 Dy2 O6 1.5(17) . . . . ? C17 O9 Dy2 O6 -90.5(18) . . . 2_556 ? C17 O9 Dy2 O9 -43.9(17) . . . 2_556 ? C17 O9 Dy2 O11 99.3(18) . . . 2_556 ? C17 O9 Dy2 O11 164.1(18) . . . . ? C17 O9 Dy2 O7 79.8(17) . . . . ? C17 O9 Dy2 O7 -156.4(15) . . . 2_556 ? C17 O9 Dy2 O9' -33.8(13) . . . . ? C17 O9 Dy2 O9' -48(2) . . . 2_556 ? C17' O9' Dy2 O6 -107.1(13) . . . . ? C17' O9' Dy2 O6 155.8(14) . . . 2_556 ? C17' O9' Dy2 O9 -150.6(12) . . . 2_556 ? C17' O9' Dy2 O9 36.0(13) . . . . ? C17' O9' Dy2 O11 -23.8(17) . . . 2_556 ? C17' O9' Dy2 O11 52.7(14) . . . . ? C17' O9' Dy2 O7 -26.1(13) . . . . ? C17' O9' Dy2 O7 102.7(13) . . . 2_556 ? C17' O9' Dy2 O9' -155.0(14) . . . 2_556 ? O3 Dy1 O1 C4 68.0(3) 6 . . . ? O2 Dy1 O1 C4 155.6(3) 6 . . . ? O8 Dy1 O1 C4 143.3(3) 1_545 . . . ? O5 Dy1 O1 C4 -77.3(3) . . . . ? O10 Dy1 O1 C4 -145.2(3) . . . . ? N3 Dy1 O1 C4 -49.0(4) . . . . ? N1 Dy1 O1 C4 2.6(3) . . . . ? O3 Dy1 O5 C12 71.4(4) 6 . . . ? O2 Dy1 O5 C12 -46.5(4) 6 . . . ? O1 Dy1 O5 C12 159.7(4) . . . . ? O8 Dy1 O5 C12 -145.3(3) 1_545 . . . ? O10 Dy1 O5 C12 -100.0(4) . . . . ? N3 Dy1 O5 C12 2.6(3) . . . . ? N1 Dy1 O5 C12 90.7(4) . . . . ? O6 Dy2 O6 C12 88.5(5) 2_556 . . . ? O9 Dy2 O6 C12 173.4(6) 2_556 . . . ? O9 Dy2 O6 C12 11.1(6) . . . . ? O11 Dy2 O6 C12 -122.7(5) 2_556 . . . ? O11 Dy2 O6 C12 -19.7(7) . . . . ? O7 Dy2 O6 C12 -58.4(5) . . . . ? O7 Dy2 O6 C12 157.5(5) 2_556 . . . ? O9' Dy2 O6 C12 19.6(5) . . . . ? O9' Dy2 O6 C12 160.7(6) 2_556 . . . ? O6 Dy2 O7 C13 20.2(6) . . . . ? O6 Dy2 O7 C13 -52.8(7) 2_556 . . . ? O9 Dy2 O7 C13 86.3(7) 2_556 . . . ? O9 Dy2 O7 C13 -69.5(7) . . . . ? O11 Dy2 O7 C13 125.6(6) 2_556 . . . ? O11 Dy2 O7 C13 -139.5(6) . . . . ? O7 Dy2 O7 C13 174.7(6) 2_556 . . . ? O9' Dy2 O7 C13 -55.9(6) . . . . ? O9' Dy2 O7 C13 70.6(7) 2_556 . . . ? O3 Dy1 O10 O12 -170.9(2) 6 . . . ? O2 Dy1 O10 O12 -133.6(3) 6 . . . ? O1 Dy1 O10 O12 71.2(3) . . . . ? O8 Dy1 O10 O12 146.1(3) 1_545 . . . ? O5 Dy1 O10 O12 1.2(3) . . . . ? N3 Dy1 O10 O12 -61.1(3) . . . . ? N1 Dy1 O10 O12 18.3(4) . . . . ? O3 Dy1 N1 C3 53.9(4) 6 . . . ? O2 Dy1 N1 C3 5.7(5) 6 . . . ? O1 Dy1 N1 C3 167.3(5) . . . . ? O8 Dy1 N1 C3 117.5(4) 1_545 . . . ? O5 Dy1 N1 C3 -115.2(4) . . . . ? O10 Dy1 N1 C3 -131.8(4) . . . . ? N3 Dy1 N1 C3 -48.8(4) . . . . ? O3 Dy1 N1 C1 -110.3(3) 6 . . . ? O2 Dy1 N1 C1 -158.4(2) 6 . . . ? O1 Dy1 N1 C1 3.1(2) . . . . ? O8 Dy1 N1 C1 -46.7(3) 1_545 . . . ? O5 Dy1 N1 C1 80.7(3) . . . . ? O10 Dy1 N1 C1 64.0(3) . . . . ? N3 Dy1 N1 C1 147.0(3) . . . . ? O3 Dy1 N3 C11 30.4(4) 6 . . . ? O2 Dy1 N3 C11 -42.8(4) 6 . . . ? O1 Dy1 N3 C11 149.0(4) . . . . ? O8 Dy1 N3 C11 -55.3(5) 1_545 . . . ? O5 Dy1 N3 C11 178.8(5) . . . . ? O10 Dy1 N3 C11 -114.5(4) . . . . ? N1 Dy1 N3 C11 102.7(4) . . . . ? O3 Dy1 N3 C9 -151.1(3) 6 . . . ? O2 Dy1 N3 C9 135.7(3) 6 . . . ? O1 Dy1 N3 C9 -32.6(3) . . . . ? O8 Dy1 N3 C9 123.2(3) 1_545 . . . ? O5 Dy1 N3 C9 -2.7(3) . . . . ? O10 Dy1 N3 C9 64.0(3) . . . . ? N1 Dy1 N3 C9 -78.8(3) . . . . ? C3 N1 C1 C2 -0.1(4) . . . . ? Dy1 N1 C1 C2 169.4(3) . . . . ? C3 N1 C1 C4 -177.1(3) . . . . ? Dy1 N1 C1 C4 -7.7(4) . . . . ? N1 C1 C2 N2 -0.1(4) . . . . ? C4 C1 C2 N2 176.3(4) . . . . ? N1 C1 C2 C5 -173.5(4) . . . . ? C4 C1 C2 C5 2.8(8) . . . . ? C3 N2 C2 C1 0.1(5) . . . . ? C3 N2 C2 C5 175.1(4) . . . . ? C1 N1 C3 N2 0.2(5) . . . . ? Dy1 N1 C3 N2 -164.8(3) . . . . ? C1 N1 C3 C6 -178.9(4) . . . . ? Dy1 N1 C3 C6 16.1(7) . . . . ? C2 N2 C3 N1 -0.2(5) . . . . ? C2 N2 C3 C6 178.9(4) . . . . ? Dy1 O2 C4 O1 -163.7(3) 6_556 . . . ? Dy1 O2 C4 C1 18.3(7) 6_556 . . . ? Dy1 O1 C4 O2 174.3(3) . . . . ? Dy1 O1 C4 C1 -7.6(5) . . . . ? C2 C1 C4 O2 11.9(7) . . . . ? N1 C1 C4 O2 -171.9(3) . . . . ? C2 C1 C4 O1 -166.2(4) . . . . ? N1 C1 C4 O1 10.0(5) . . . . ? Dy1 O3 C5 O4 146.7(4) 6_556 . . . ? Dy1 O3 C5 C2 -34.8(7) 6_556 . . . ? C1 C2 C5 O4 168.5(5) . . . . ? N2 C2 C5 O4 -4.3(6) . . . . ? C1 C2 C5 O3 -10.2(7) . . . . ? N2 C2 C5 O3 177.0(4) . . . . ? N1 C3 C6 C7 -90.6(6) . . . . ? N2 C3 C6 C7 90.4(6) . . . . ? C3 C6 C7 C8 -168.7(5) . . . . ? C11 N3 C9 C10 0.0(5) . . . . ? Dy1 N3 C9 C10 -179.0(3) . . . . ? C11 N3 C9 C12 -178.1(4) . . . . ? Dy1 N3 C9 C12 3.0(4) . . . . ? N3 C9 C10 N4 -0.4(5) . . . . ? C12 C9 C10 N4 177.2(4) . . . . ? N3 C9 C10 C13 -173.4(5) . . . . ? C12 C9 C10 C13 4.2(9) . . . . ? C11 N4 C10 C9 0.6(5) . . . . ? C11 N4 C10 C13 175.2(4) . . . . ? C9 N3 C11 N4 0.4(5) . . . . ? Dy1 N3 C11 N4 179.0(3) . . . . ? C9 N3 C11 C14 -179.8(4) . . . . ? Dy1 N3 C11 C14 -1.2(7) . . . . ? C10 N4 C11 N3 -0.7(5) . . . . ? C10 N4 C11 C14 179.5(4) . . . . ? Dy2 O6 C12 O5 -131.6(4) . . . . ? Dy2 O6 C12 C9 51.0(7) . . . . ? Dy1 O5 C12 O6 -179.5(3) . . . . ? Dy1 O5 C12 C9 -2.0(5) . . . . ? C10 C9 C12 O6 -0.8(7) . . . . ? N3 C9 C12 O6 176.7(4) . . . . ? C10 C9 C12 O5 -178.4(4) . . . . ? N3 C9 C12 O5 -1.0(6) . . . . ? Dy2 O7 C13 O8 -174.0(4) . . . . ? Dy2 O7 C13 C10 6.6(8) . . . . ? Dy1 O8 C13 O7 22.6(7) 1_565 . . . ? Dy1 O8 C13 C10 -158.1(3) 1_565 . . . ? C9 C10 C13 O7 -23.6(8) . . . . ? N4 C10 C13 O7 164.0(4) . . . . ? C9 C10 C13 O8 157.0(5) . . . . ? N4 C10 C13 O8 -15.4(6) . . . . ? N3 C11 C14 C15 112.2(5) . . . . ? N4 C11 C14 C15 -68.0(6) . . . . ? C11 C14 C15 C16 -170.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O4 0.86 2.21 2.997(5) 152.7 7_557 O12 H6W O5 0.84 2.12 2.945(5) 164.4 2_556 O12 H5W O9' 0.85 2.30 3.143(12) 179.3 . O11 H3W O2 0.84 2.59 3.040(4) 114.3 2_566 O11 H4W O1 0.85 2.05 2.883(4) 168.5 2_566 O11 H3W O2 0.84 2.59 3.040(4) 114.3 2_566 O11 H3W O10 0.84 2.39 3.169(5) 153.5 5_566 O10 H2W O12 0.85 1.86 2.697(5) 170.2 . O10 H1W O7 0.85 2.51 3.149(5) 132.5 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.200 _refine_diff_density_min -1.918 _refine_diff_density_rms 0.115 # Attachment '- 5.ho.cif' data_5ho _database_code_depnum_ccdc_archive 'CCDC 765406' #TrackingRef '- 5.ho.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H45 Ho3 N8 O24' _chemical_formula_weight 1432.56 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 C2/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 35.027(4) _cell_length_b 9.1238(10) _cell_length_c 13.1216(14) _cell_angle_alpha 90.00 _cell_angle_beta 94.9310(10) _cell_angle_gamma 90.00 _cell_volume 4177.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5482 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2768 _exptl_absorpt_coefficient_mu 5.730 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2390 _exptl_absorpt_correction_T_max 0.4090 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15141 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3872 _reflns_number_gt 3366 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+14.4904P] 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 3872 _refine_ls_number_parameters 327 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.033 _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 C17 C 0.0000 0.5000 0.5000 0.0397(2) Uani 0.426(7) 2 d SPDU . 1 H17A H 0.0064 0.4042 0.5244 0.048 Uiso 0.213(3) 1 d PR . 1 O9 O -0.0080(2) 0.5679(7) 0.5741(4) 0.0393(2) Uani 0.426(7) 1 d PDU . 1 C17' C 0.0000 0.5000 0.5000 0.0397(2) Uani 0.574(7) 2 d SPDU . 2 H17B H -0.0064 0.5958 0.4756 0.048 Uiso 0.287(3) 1 d PR . 2 O9' O -0.00402(15) 0.5052(7) 0.5860(3) 0.0392(2) Uani 0.574(7) 1 d PDU . 2 Ho1 Ho 0.108693(5) 0.069471(17) 0.629837(12) 0.01782(4) Uani 1 1 d . . . Ho2 Ho 0.0000 0.62029(3) 0.7500 0.02021(6) Uani 1 2 d S . . O1 O 0.09907(7) -0.0422(3) 0.78540(18) 0.0230(6) Uani 1 1 d . . . O2 O 0.10633(8) -0.0691(3) 0.95298(19) 0.0265(7) Uani 1 1 d . . . O3 O 0.16888(7) 0.0011(3) 1.09895(19) 0.0269(7) Uani 1 1 d . . . O4 O 0.22243(8) 0.1317(3) 1.0870(2) 0.0370(8) Uani 1 1 d . . . O5 O 0.07068(8) 0.2311(3) 0.72264(19) 0.0278(7) Uani 1 1 d . . . O6 O 0.04591(8) 0.4462(3) 0.7584(2) 0.0352(7) Uani 1 1 d . . . O7 O 0.04863(8) 0.7328(3) 0.6620(2) 0.0307(7) Uani 1 1 d . . . O8 O 0.09792(7) 0.8220(3) 0.58616(19) 0.0258(7) Uani 1 1 d . . . O10 O 0.04281(9) 0.0480(3) 0.5672(3) 0.0523(10) Uani 1 1 d . . . H1W H 0.0317 -0.0337 0.5696 0.078 Uiso 1 1 d R . . H2W H 0.0207 0.0770 0.5802 0.078 Uiso 1 1 d R . . O11 O -0.03353(9) 0.8049(3) 0.6519(2) 0.0454(9) Uani 1 1 d . . . H3W H -0.0397 0.8164 0.5891 0.068 Uiso 1 1 d R . . H4W H -0.0510 0.8525 0.6780 0.068 Uiso 1 1 d R . . O12 O -0.02447(10) 0.1718(5) 0.6066(3) 0.0760(13) Uani 1 1 d . . . H5W H -0.0188 0.2608 0.6006 0.114 Uiso 1 1 d R . . H6W H -0.0342 0.1811 0.6628 0.114 Uiso 1 1 d R . . N1 N 0.15304(9) 0.1646(3) 0.7808(2) 0.0237(8) Uani 1 1 d . . . N2 N 0.19956(9) 0.2282(3) 0.8960(2) 0.0279(8) Uani 1 1 d . . . H2 H 0.2198 0.2711 0.9229 0.033 Uiso 1 1 calc R . . N3 N 0.11159(9) 0.3359(3) 0.5766(2) 0.0228(8) Uani 1 1 d . . . N4 N 0.11776(9) 0.5582(3) 0.5171(2) 0.0264(8) Uani 1 1 d . . . H4 H 0.1256 0.6295 0.4815 0.032 Uiso 1 1 calc R . . C1 C 0.14818(10) 0.0932(4) 0.8732(3) 0.0213(9) Uani 1 1 d . . . C2 C 0.17734(10) 0.1315(4) 0.9453(3) 0.0216(9) Uani 1 1 d . . . C3 C 0.18446(11) 0.2450(4) 0.7986(3) 0.0255(9) Uani 1 1 d . . . C4 C 0.11585(10) -0.0109(4) 0.8725(2) 0.0183(8) Uani 1 1 d . . . C5 C 0.19051(11) 0.0850(4) 1.0528(3) 0.0253(10) Uani 1 1 d . . . C6 C 0.20211(12) 0.3448(5) 0.7268(3) 0.0334(11) Uani 1 1 d . . . H6A H 0.2139 0.4259 0.7655 0.040 Uiso 1 1 calc R . . H6B H 0.1820 0.3849 0.6795 0.040 Uiso 1 1 calc R . . C7 C 0.23144(15) 0.2759(5) 0.6666(4) 0.0538(14) Uani 1 1 d . . . H7A H 0.2190 0.2088 0.6169 0.065 Uiso 1 1 calc R . . H7B H 0.2492 0.2199 0.7120 0.065 Uiso 1 1 calc R . . C8 C 0.25356(15) 0.3916(6) 0.6109(4) 0.0632(17) Uani 1 1 d . . . H8A H 0.2358 0.4528 0.5706 0.095 Uiso 1 1 calc R . . H8B H 0.2703 0.3440 0.5671 0.095 Uiso 1 1 calc R . . H8C H 0.2684 0.4507 0.6602 0.095 Uiso 1 1 calc R . . C9 C 0.08801(11) 0.4300(4) 0.6257(3) 0.0202(9) Uani 1 1 d . . . C10 C 0.09169(11) 0.5704(4) 0.5899(3) 0.0214(9) Uani 1 1 d . . . C11 C 0.12905(11) 0.4166(4) 0.5104(3) 0.0232(9) Uani 1 1 d . . . C12 C 0.06655(11) 0.3668(4) 0.7076(3) 0.0224(9) Uani 1 1 d . . . C13 C 0.07780(11) 0.7186(4) 0.6156(3) 0.0236(9) Uani 1 1 d . . . C14 C 0.15698(12) 0.3649(4) 0.4394(3) 0.0289(10) Uani 1 1 d . . . H14A H 0.1637 0.2637 0.4553 0.035 Uiso 1 1 calc R . . H14B H 0.1802 0.4231 0.4496 0.035 Uiso 1 1 calc R . . C15 C 0.14118(13) 0.3756(5) 0.3276(3) 0.0334(11) Uani 1 1 d . . . H15A H 0.1161 0.3299 0.3193 0.040 Uiso 1 1 calc R . . H15B H 0.1382 0.4780 0.3086 0.040 Uiso 1 1 calc R . . C16 C 0.16740(13) 0.3015(5) 0.2573(3) 0.0365(11) Uani 1 1 d . . . H16A H 0.1929 0.3398 0.2702 0.055 Uiso 1 1 calc R . . H16B H 0.1583 0.3199 0.1874 0.055 Uiso 1 1 calc R . . H16C H 0.1677 0.1978 0.2698 0.055 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 C17 0.0397(4) 0.0402(4) 0.0391(4) -0.0006(4) 0.0038(4) 0.0001(4) O9 0.0395(4) 0.0399(4) 0.0387(4) -0.0004(4) 0.0039(4) 0.0001(4) C17' 0.0397(4) 0.0403(4) 0.0391(4) -0.0006(4) 0.0038(4) 0.0001(4) O9' 0.0394(4) 0.0398(4) 0.0386(4) -0.0004(4) 0.0040(4) 0.0000(4) Ho1 0.02421(9) 0.01194(8) 0.01741(8) 0.00093(6) 0.00231(7) 0.00088(6) Ho2 0.02363(12) 0.01464(11) 0.02275(12) 0.000 0.00426(10) 0.000 O1 0.0331(14) 0.0179(12) 0.0174(12) -0.0002(10) -0.0024(11) -0.0062(11) O2 0.0351(15) 0.0201(13) 0.0244(13) 0.0010(10) 0.0026(12) -0.0058(11) O3 0.0255(13) 0.0307(14) 0.0250(13) 0.0069(12) 0.0059(11) 0.0006(12) O4 0.0288(15) 0.0499(18) 0.0308(15) 0.0026(13) -0.0055(13) -0.0158(14) O5 0.0377(15) 0.0151(13) 0.0325(14) 0.0020(11) 0.0149(12) 0.0065(12) O6 0.0481(17) 0.0275(15) 0.0333(15) 0.0052(12) 0.0224(13) 0.0136(13) O7 0.0330(15) 0.0141(13) 0.0472(16) -0.0030(12) 0.0161(13) -0.0032(12) O8 0.0324(14) 0.0139(12) 0.0321(14) -0.0031(11) 0.0087(12) -0.0022(11) O10 0.0257(16) 0.0407(18) 0.090(2) -0.0270(17) 0.0005(17) 0.0020(14) O11 0.0499(18) 0.0525(19) 0.0351(16) 0.0155(14) 0.0121(14) 0.0280(15) O12 0.057(2) 0.087(3) 0.085(3) -0.037(2) 0.015(2) 0.012(2) N1 0.0275(17) 0.0207(16) 0.0236(15) 0.0020(13) 0.0059(13) -0.0018(14) N2 0.0324(18) 0.0267(17) 0.0243(16) -0.0011(13) 0.0015(14) -0.0077(15) N3 0.0276(17) 0.0171(15) 0.0239(15) -0.0030(12) 0.0033(13) 0.0015(13) N4 0.0379(19) 0.0163(16) 0.0267(16) 0.0009(12) 0.0119(15) -0.0025(14) C1 0.0250(19) 0.0198(18) 0.0189(17) 0.0014(14) 0.0015(15) 0.0051(15) C2 0.0225(19) 0.0166(18) 0.0265(18) 0.0009(15) 0.0055(16) -0.0024(15) C3 0.0259(19) 0.0226(19) 0.0279(19) 0.0020(16) 0.0009(16) 0.0008(17) C4 0.0236(19) 0.0127(17) 0.0183(17) 0.0002(14) 0.0003(15) 0.0011(15) C5 0.028(2) 0.026(2) 0.0224(19) -0.0033(15) 0.0038(16) 0.0012(17) C6 0.032(2) 0.032(2) 0.035(2) 0.0119(18) 0.0006(19) -0.0032(19) C7 0.064(3) 0.037(3) 0.065(3) 0.003(2) 0.033(3) -0.002(2) C8 0.054(3) 0.072(4) 0.067(3) 0.012(3) 0.024(3) -0.017(3) C9 0.0238(19) 0.0154(17) 0.0214(18) -0.0044(14) 0.0023(15) 0.0005(15) C10 0.0263(19) 0.0157(18) 0.0227(18) -0.0032(14) 0.0050(16) 0.0011(15) C11 0.027(2) 0.0175(18) 0.0255(19) 0.0020(15) 0.0037(16) 0.0011(16) C12 0.0244(19) 0.0199(19) 0.0232(18) 0.0017(15) 0.0035(16) 0.0017(15) C13 0.030(2) 0.0149(18) 0.0261(19) -0.0022(14) 0.0009(17) -0.0028(16) C14 0.038(2) 0.0192(19) 0.031(2) -0.0014(16) 0.0109(18) -0.0028(17) C15 0.041(2) 0.031(2) 0.028(2) -0.0003(17) 0.0077(19) 0.0039(19) C16 0.037(2) 0.037(2) 0.036(2) -0.0048(19) 0.008(2) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C17 O9 1.206(6) . ? C17 O9 1.206(6) 5_566 ? C17 H17A 0.9509 . ? C17 H17B 0.9508 . ? O9 Ho2 2.350(6) . ? C17' O9' 1.151(4) . ? C17' O9' 1.151(4) 5_566 ? C17' H17A 0.9509 . ? C17' H17B 0.9508 . ? O9' Ho2 2.387(5) . ? O9' H17A 1.2981 . ? Ho1 O3 2.274(3) 6 ? Ho1 O2 2.315(3) 6 ? Ho1 O1 2.332(2) . ? Ho1 O8 2.352(2) 1_545 ? Ho1 O5 2.390(3) . ? Ho1 O10 2.390(3) . ? Ho1 N3 2.534(3) . ? Ho1 N1 2.561(3) . ? Ho2 O6 2.256(3) 2_556 ? Ho2 O6 2.256(3) . ? Ho2 O9 2.350(6) 2_556 ? Ho2 O11 2.369(3) 2_556 ? Ho2 O11 2.369(3) . ? Ho2 O7 2.372(3) 2_556 ? Ho2 O7 2.372(3) . ? Ho2 O9' 2.387(5) 2_556 ? O1 C4 1.272(4) . ? O2 C4 1.252(4) . ? O2 Ho1 2.315(3) 6_556 ? O3 C5 1.267(5) . ? O3 Ho1 2.274(3) 6_556 ? O4 C5 1.244(5) . ? O5 C12 1.259(4) . ? O6 C12 1.255(5) . ? O7 C13 1.240(5) . ? O8 C13 1.258(4) . ? O8 Ho1 2.352(2) 1_565 ? O10 O12 2.703(5) . ? O10 H1W 0.8432 . ? O10 H2W 0.8479 . ? O11 H3W 0.8410 . ? O11 H4W 0.8458 . ? O12 H5W 0.8420 . ? O12 H6W 0.8427 . ? N1 C3 1.327(5) . ? N1 C1 1.400(5) . ? N2 C3 1.349(5) . ? N2 C2 1.375(5) . ? N2 H2 0.8600 . ? N3 C11 1.327(5) . ? N3 C9 1.388(5) . ? N4 C11 1.356(5) . ? N4 C10 1.381(5) . ? N4 H4 0.8600 . ? C1 C2 1.377(5) . ? C1 C4 1.477(5) . ? C2 C5 1.506(5) . ? C3 C6 1.483(5) . ? C6 C7 1.488(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.532(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.375(5) . ? C9 C12 1.481(5) . ? C10 C13 1.486(5) . ? C11 C14 1.485(5) . ? C14 C15 1.526(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.516(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 O9 C17 O9 180.0(3) . 5_566 ? O9 C17 H17A 105.3 . . ? O9 C17 H17A 74.7 5_566 . ? O9 C17 H17B 74.7 . . ? O9 C17 H17B 105.3 5_566 . ? H17A C17 H17B 180.0 . . ? C17 O9 Ho2 151.6(5) . . ? C17 O9 H17B 43.8 . . ? Ho2 O9 H17B 155.3 . . ? O9' C17' O9' 180.000(1) . 5_566 ? O9' C17' H17A 75.6 . . ? O9' C17' H17A 104.4 5_566 . ? O9' C17' H17B 104.4 . . ? O9' C17' H17B 75.6 5_566 . ? H17A C17' H17B 180.0 . . ? C17' O9' Ho2 154.1(4) . . ? C17' O9' H17A 45.2 . . ? Ho2 O9' H17A 151.1 . . ? O3 Ho1 O2 76.97(9) 6 6 ? O3 Ho1 O1 103.79(9) 6 . ? O2 Ho1 O1 151.83(8) 6 . ? O3 Ho1 O8 79.43(9) 6 1_545 ? O2 Ho1 O8 76.30(9) 6 1_545 ? O1 Ho1 O8 76.21(8) . 1_545 ? O3 Ho1 O5 146.24(9) 6 . ? O2 Ho1 O5 122.57(9) 6 . ? O1 Ho1 O5 72.23(9) . . ? O8 Ho1 O5 129.20(9) 1_545 . ? O3 Ho1 O10 142.95(10) 6 . ? O2 Ho1 O10 72.85(11) 6 . ? O1 Ho1 O10 93.28(11) . . ? O8 Ho1 O10 73.00(10) 1_545 . ? O5 Ho1 O10 70.24(10) . . ? O3 Ho1 N3 99.36(10) 6 . ? O2 Ho1 N3 73.96(9) 6 . ? O1 Ho1 N3 132.29(9) . . ? O8 Ho1 N3 149.68(9) 1_545 . ? O5 Ho1 N3 65.52(9) . . ? O10 Ho1 N3 92.53(10) . . ? O3 Ho1 N1 73.97(9) 6 . ? O2 Ho1 N1 137.96(10) 6 . ? O1 Ho1 N1 66.10(9) . . ? O8 Ho1 N1 126.00(9) 1_545 . ? O5 Ho1 N1 73.99(9) . . ? O10 Ho1 N1 142.85(11) . . ? N3 Ho1 N1 81.49(9) . . ? O6 Ho2 O6 90.49(15) 2_556 . ? O6 Ho2 O9 77.55(19) 2_556 . ? O6 Ho2 O9 85.95(18) . . ? O6 Ho2 O9 85.95(18) 2_556 2_556 ? O6 Ho2 O9 77.55(19) . 2_556 ? O9 Ho2 O9 156.5(3) . 2_556 ? O6 Ho2 O11 147.68(10) 2_556 2_556 ? O6 Ho2 O11 98.98(11) . 2_556 ? O9 Ho2 O11 133.61(19) . 2_556 ? O9 Ho2 O11 66.38(18) 2_556 2_556 ? O6 Ho2 O11 98.98(11) 2_556 . ? O6 Ho2 O11 147.68(10) . . ? O9 Ho2 O11 66.38(18) . . ? O9 Ho2 O11 133.61(19) 2_556 . ? O11 Ho2 O11 89.37(15) 2_556 . ? O6 Ho2 O7 77.87(9) 2_556 2_556 ? O6 Ho2 O7 145.03(9) . 2_556 ? O9 Ho2 O7 122.40(18) . 2_556 ? O9 Ho2 O7 68.90(18) 2_556 2_556 ? O11 Ho2 O7 76.78(10) 2_556 2_556 ? O11 Ho2 O7 67.26(10) . 2_556 ? O6 Ho2 O7 145.03(9) 2_556 . ? O6 Ho2 O7 77.87(9) . . ? O9 Ho2 O7 68.90(19) . . ? O9 Ho2 O7 122.40(18) 2_556 . ? O11 Ho2 O7 67.26(10) 2_556 . ? O11 Ho2 O7 76.78(10) . . ? O7 Ho2 O7 128.73(12) 2_556 . ? O6 Ho2 O9' 73.79(15) 2_556 2_556 ? O6 Ho2 O9' 70.10(15) . 2_556 ? O9 Ho2 O9' 142.0(2) . 2_556 ? O9 Ho2 O9' 14.69(19) 2_556 2_556 ? O11 Ho2 O9' 80.51(16) 2_556 2_556 ? O11 Ho2 O9' 142.21(15) . 2_556 ? O7 Ho2 O9' 74.98(15) 2_556 2_556 ? O7 Ho2 O9' 129.78(14) . 2_556 ? O6 Ho2 O9' 70.10(15) 2_556 . ? O6 Ho2 O9' 73.79(15) . . ? O9 Ho2 O9' 14.69(19) . . ? O9 Ho2 O9' 142.0(2) 2_556 . ? O11 Ho2 O9' 142.21(15) 2_556 . ? O11 Ho2 O9' 80.51(15) . . ? O7 Ho2 O9' 129.78(14) 2_556 . ? O7 Ho2 O9' 74.98(15) . . ? O9' Ho2 O9' 127.8(3) 2_556 . ? C4 O1 Ho1 126.7(2) . . ? C4 O2 Ho1 148.9(2) . 6_556 ? C5 O3 Ho1 149.1(2) . 6_556 ? C12 O5 Ho1 126.0(2) . . ? C12 O6 Ho2 145.2(2) . . ? C13 O7 Ho2 148.2(2) . . ? C13 O8 Ho1 136.7(2) . 1_565 ? Ho1 O10 O12 137.05(16) . . ? Ho1 O10 H1W 119.8 . . ? O12 O10 H1W 87.0 . . ? Ho1 O10 H2W 140.9 . . ? O12 O10 H2W 6.5 . . ? H1W O10 H2W 80.5 . . ? Ho2 O11 H3W 134.0 . . ? Ho2 O11 H4W 119.1 . . ? H3W O11 H4W 101.5 . . ? O10 O12 H5W 99.7 . . ? O10 O12 H6W 129.5 . . ? H5W O12 H6W 95.8 . . ? C3 N1 C1 105.4(3) . . ? C3 N1 Ho1 139.7(2) . . ? C1 N1 Ho1 113.6(2) . . ? C3 N2 C2 109.1(3) . . ? C3 N2 H2 125.4 . . ? C2 N2 H2 125.4 . . ? C11 N3 C9 106.7(3) . . ? C11 N3 Ho1 138.1(2) . . ? C9 N3 Ho1 115.2(2) . . ? C11 N4 C10 109.6(3) . . ? C11 N4 H4 125.2 . . ? C10 N4 H4 125.2 . . ? C2 C1 N1 109.8(3) . . ? C2 C1 C4 133.6(3) . . ? N1 C1 C4 116.4(3) . . ? N2 C2 C1 104.8(3) . . ? N2 C2 C5 118.8(3) . . ? C1 C2 C5 136.2(3) . . ? N1 C3 N2 110.8(3) . . ? N1 C3 C6 127.8(3) . . ? N2 C3 C6 121.4(3) . . ? O2 C4 O1 121.8(3) . . ? O2 C4 C1 121.8(3) . . ? O1 C4 C1 116.4(3) . . ? O4 C5 O3 126.2(3) . . ? O4 C5 C2 115.8(3) . . ? O3 C5 C2 118.1(3) . . ? C3 C6 C7 115.0(4) . . ? C3 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? C3 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C8 111.3(4) . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N3 109.9(3) . . ? C10 C9 C12 132.8(3) . . ? N3 C9 C12 117.1(3) . . ? C9 C10 N4 104.4(3) . . ? C9 C10 C13 136.7(4) . . ? N4 C10 C13 118.7(3) . . ? N3 C11 N4 109.5(3) . . ? N3 C11 C14 126.8(3) . . ? N4 C11 C14 123.7(3) . . ? O6 C12 O5 123.2(3) . . ? O6 C12 C9 120.8(3) . . ? O5 C12 C9 116.0(3) . . ? O7 C13 O8 125.4(3) . . ? O7 C13 C10 120.4(3) . . ? O8 C13 C10 114.2(3) . . ? C11 C14 C15 112.3(3) . . ? C11 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C11 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 111.6(3) . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O9 C17 O9 Ho2 -62.2(11) 5_566 . . . ? O9' C17' O9' Ho2 66(2) 5_566 . . . ? C17 O9 Ho2 O6 -90.3(10) . . . 2_556 ? C17 O9 Ho2 O6 1.1(10) . . . . ? C17 O9 Ho2 O9 -44.0(10) . . . 2_556 ? C17 O9 Ho2 O11 99.6(10) . . . 2_556 ? C17 O9 Ho2 O11 164.0(11) . . . . ? C17 O9 Ho2 O7 -157.1(9) . . . 2_556 ? C17 O9 Ho2 O7 79.6(10) . . . . ? C17 O9 Ho2 O9' -48.7(13) . . . 2_556 ? C17 O9 Ho2 O9' -32.5(7) . . . . ? C17' O9' Ho2 O6 156.3(9) . . . 2_556 ? C17' O9' Ho2 O6 -107.1(9) . . . . ? C17' O9' Ho2 O9 37.8(9) . . . . ? C17' O9' Ho2 O9 -149.6(8) . . . 2_556 ? C17' O9' Ho2 O11 -23.4(11) . . . 2_556 ? C17' O9' Ho2 O11 53.1(9) . . . . ? C17' O9' Ho2 O7 102.6(9) . . . 2_556 ? C17' O9' Ho2 O7 -25.7(9) . . . . ? C17' O9' Ho2 O9' -154.7(9) . . . 2_556 ? O3 Ho1 O1 C4 68.7(3) 6 . . . ? O2 Ho1 O1 C4 156.8(3) 6 . . . ? O8 Ho1 O1 C4 144.0(3) 1_545 . . . ? O5 Ho1 O1 C4 -76.4(3) . . . . ? O10 Ho1 O1 C4 -144.4(3) . . . . ? N3 Ho1 O1 C4 -48.0(3) . . . . ? N1 Ho1 O1 C4 3.5(3) . . . . ? O3 Ho1 O5 C12 71.4(3) 6 . . . ? O2 Ho1 O5 C12 -46.9(3) 6 . . . ? O1 Ho1 O5 C12 159.8(3) . . . . ? O8 Ho1 O5 C12 -146.0(3) 1_545 . . . ? O10 Ho1 O5 C12 -99.9(3) . . . . ? N3 Ho1 O5 C12 2.5(3) . . . . ? N1 Ho1 O5 C12 90.3(3) . . . . ? O6 Ho2 O6 C12 90.1(5) 2_556 . . . ? O9 Ho2 O6 C12 12.6(5) . . . . ? O9 Ho2 O6 C12 175.9(5) 2_556 . . . ? O11 Ho2 O6 C12 -120.9(5) 2_556 . . . ? O11 Ho2 O6 C12 -17.7(6) . . . . ? O7 Ho2 O6 C12 159.4(4) 2_556 . . . ? O7 Ho2 O6 C12 -56.6(4) . . . . ? O9' Ho2 O6 C12 162.7(5) 2_556 . . . ? O9' Ho2 O6 C12 21.0(5) . . . . ? O6 Ho2 O7 C13 -53.3(5) 2_556 . . . ? O6 Ho2 O7 C13 19.7(5) . . . . ? O9 Ho2 O7 C13 -70.6(5) . . . . ? O9 Ho2 O7 C13 86.3(5) 2_556 . . . ? O11 Ho2 O7 C13 125.0(5) 2_556 . . . ? O11 Ho2 O7 C13 -140.0(5) . . . . ? O7 Ho2 O7 C13 174.2(5) 2_556 . . . ? O9' Ho2 O7 C13 70.6(5) 2_556 . . . ? O9' Ho2 O7 C13 -56.5(5) . . . . ? O3 Ho1 O10 O12 -170.8(2) 6 . . . ? O2 Ho1 O10 O12 -133.9(3) 6 . . . ? O1 Ho1 O10 O12 71.0(2) . . . . ? O8 Ho1 O10 O12 145.6(3) 1_545 . . . ? O5 Ho1 O10 O12 1.3(2) . . . . ? N3 Ho1 O10 O12 -61.6(3) . . . . ? N1 Ho1 O10 O12 17.7(3) . . . . ? O3 Ho1 N1 C3 53.5(4) 6 . . . ? O2 Ho1 N1 C3 5.5(5) 6 . . . ? O1 Ho1 N1 C3 167.0(4) . . . . ? O8 Ho1 N1 C3 117.1(4) 1_545 . . . ? O5 Ho1 N1 C3 -115.7(4) . . . . ? O10 Ho1 N1 C3 -131.7(4) . . . . ? N3 Ho1 N1 C3 -48.8(4) . . . . ? O3 Ho1 N1 C1 -111.1(2) 6 . . . ? O2 Ho1 N1 C1 -159.1(2) 6 . . . ? O1 Ho1 N1 C1 2.4(2) . . . . ? O8 Ho1 N1 C1 -47.5(3) 1_545 . . . ? O5 Ho1 N1 C1 79.7(2) . . . . ? O10 Ho1 N1 C1 63.6(3) . . . . ? N3 Ho1 N1 C1 146.5(3) . . . . ? O3 Ho1 N3 C11 30.6(4) 6 . . . ? O2 Ho1 N3 C11 -42.8(4) 6 . . . ? O1 Ho1 N3 C11 149.1(3) . . . . ? O8 Ho1 N3 C11 -54.5(4) 1_545 . . . ? O5 Ho1 N3 C11 178.9(4) . . . . ? O10 Ho1 N3 C11 -114.2(4) . . . . ? N1 Ho1 N3 C11 102.7(4) . . . . ? O3 Ho1 N3 C9 -151.8(2) 6 . . . ? O2 Ho1 N3 C9 134.8(3) 6 . . . ? O1 Ho1 N3 C9 -33.3(3) . . . . ? O8 Ho1 N3 C9 123.2(2) 1_545 . . . ? O5 Ho1 N3 C9 -3.5(2) . . . . ? O10 Ho1 N3 C9 63.4(2) . . . . ? N1 Ho1 N3 C9 -79.7(2) . . . . ? C3 N1 C1 C2 -0.5(4) . . . . ? Ho1 N1 C1 C2 169.2(2) . . . . ? C3 N1 C1 C4 -176.9(3) . . . . ? Ho1 N1 C1 C4 -7.1(4) . . . . ? C3 N2 C2 C1 -0.7(4) . . . . ? C3 N2 C2 C5 174.7(3) . . . . ? N1 C1 C2 N2 0.8(4) . . . . ? C4 C1 C2 N2 176.2(4) . . . . ? N1 C1 C2 C5 -173.4(4) . . . . ? C4 C1 C2 C5 2.1(8) . . . . ? C1 N1 C3 N2 0.1(4) . . . . ? Ho1 N1 C3 N2 -165.3(3) . . . . ? C1 N1 C3 C6 -178.7(4) . . . . ? Ho1 N1 C3 C6 15.9(7) . . . . ? C2 N2 C3 N1 0.4(4) . . . . ? C2 N2 C3 C6 179.2(3) . . . . ? Ho1 O2 C4 O1 -164.8(3) 6_556 . . . ? Ho1 O2 C4 C1 17.7(7) 6_556 . . . ? Ho1 O1 C4 O2 173.9(2) . . . . ? Ho1 O1 C4 C1 -8.6(4) . . . . ? C2 C1 C4 O2 12.5(6) . . . . ? N1 C1 C4 O2 -172.3(3) . . . . ? C2 C1 C4 O1 -165.1(4) . . . . ? N1 C1 C4 O1 10.1(5) . . . . ? Ho1 O3 C5 O4 146.2(4) 6_556 . . . ? Ho1 O3 C5 C2 -35.2(7) 6_556 . . . ? N2 C2 C5 O4 -4.4(5) . . . . ? C1 C2 C5 O4 169.1(4) . . . . ? N2 C2 C5 O3 176.8(3) . . . . ? C1 C2 C5 O3 -9.6(7) . . . . ? N1 C3 C6 C7 -91.2(5) . . . . ? N2 C3 C6 C7 90.2(5) . . . . ? C3 C6 C7 C8 -168.8(4) . . . . ? C11 N3 C9 C10 -1.0(4) . . . . ? Ho1 N3 C9 C10 -179.3(2) . . . . ? C11 N3 C9 C12 -177.2(3) . . . . ? Ho1 N3 C9 C12 4.5(4) . . . . ? N3 C9 C10 N4 0.7(4) . . . . ? C12 C9 C10 N4 176.1(4) . . . . ? N3 C9 C10 C13 -173.4(4) . . . . ? C12 C9 C10 C13 2.0(8) . . . . ? C11 N4 C10 C9 -0.1(4) . . . . ? C11 N4 C10 C13 175.3(3) . . . . ? C9 N3 C11 N4 0.9(4) . . . . ? Ho1 N3 C11 N4 178.6(2) . . . . ? C9 N3 C11 C14 -179.6(4) . . . . ? Ho1 N3 C11 C14 -1.8(6) . . . . ? C10 N4 C11 N3 -0.5(4) . . . . ? C10 N4 C11 C14 180.0(3) . . . . ? Ho2 O6 C12 O5 -132.3(4) . . . . ? Ho2 O6 C12 C9 48.2(6) . . . . ? Ho1 O5 C12 O6 179.4(3) . . . . ? Ho1 O5 C12 C9 -1.1(5) . . . . ? C10 C9 C12 O6 1.8(6) . . . . ? N3 C9 C12 O6 177.0(3) . . . . ? C10 C9 C12 O5 -177.6(4) . . . . ? N3 C9 C12 O5 -2.5(5) . . . . ? Ho2 O7 C13 O8 -173.2(3) . . . . ? Ho2 O7 C13 C10 7.1(7) . . . . ? Ho1 O8 C13 O7 21.8(6) 1_565 . . . ? Ho1 O8 C13 C10 -158.5(2) 1_565 . . . ? C9 C10 C13 O7 -22.8(7) . . . . ? N4 C10 C13 O7 163.7(3) . . . . ? C9 C10 C13 O8 157.4(4) . . . . ? N4 C10 C13 O8 -16.1(5) . . . . ? N3 C11 C14 C15 112.9(4) . . . . ? N4 C11 C14 C15 -67.6(5) . . . . ? C11 C14 C15 C16 -171.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O10 H1W O7 0.84 2.50 3.133(4) 132.8 1_545 O10 H2W O12 0.85 1.86 2.703(5) 170.5 . O11 H3W O10 0.84 2.39 3.165(5) 153.6 5_566 O11 H3W O2 0.84 2.57 3.019(4) 114.4 2_566 O11 H4W O1 0.85 2.03 2.867(4) 168.8 2_566 O11 H3W O2 0.84 2.57 3.019(4) 114.4 2_566 O12 H5W O9' 0.84 2.30 3.142(7) 179.1 . O12 H6W O5 0.84 2.10 2.925(5) 164.4 2_556 N2 H2 O4 0.86 2.22 3.007(4) 151.8 7_557 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.340 _refine_diff_density_min -1.745 _refine_diff_density_rms 0.145 # Attachment '- 7 yb.cif' data_h _database_code_depnum_ccdc_archive 'CCDC 765407' #TrackingRef '- 7 yb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H17 N O19 Yb2' _chemical_formula_weight 813.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1983(14) _cell_length_b 10.5672(18) _cell_length_c 13.057(2) _cell_angle_alpha 94.034(2) _cell_angle_beta 103.297(2) _cell_angle_gamma 107.688(2) _cell_volume 1036.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4573 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 28.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 9.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2103 _exptl_absorpt_correction_T_max 0.3080 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7753 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3812 _reflns_number_gt 3350 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+9.4861P] 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 3812 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Yb1 Yb 0.32825(4) 1.02855(3) 0.18850(2) 0.01664(11) Uani 1 1 d . . . Yb2 Yb 0.77741(4) 0.67889(3) 0.39521(2) 0.01572(11) Uani 1 1 d . . . O1 O 0.0441(7) 0.8575(5) 0.1457(4) 0.0215(11) Uani 1 1 d . . . O2 O -0.0479(7) 0.8188(5) 0.2925(4) 0.0173(10) Uani 1 1 d . . . O3 O -0.4206(7) 0.4480(5) 0.3394(4) 0.0178(11) Uani 1 1 d . . . O4 O -0.5370(8) 0.2576(5) 0.2264(4) 0.0264(12) Uani 1 1 d . . . O5 O 0.5687(6) 1.0271(4) 0.3385(4) 0.0147(10) Uani 1 1 d . . . O6 O 0.7366(6) 0.9071(5) 0.4085(4) 0.0153(10) Uani 1 1 d . . . O7 O 0.5130(6) 0.6890(5) 0.2713(4) 0.0171(10) Uani 1 1 d . . . O8 O 0.3689(7) 0.8164(5) 0.1894(4) 0.0273(13) Uani 1 1 d . . . O9 O 0.3965(7) 0.9309(5) -0.1321(4) 0.0216(11) Uani 1 1 d . . . O10 O 0.2800(6) 0.9737(5) -0.0005(4) 0.0195(11) Uani 1 1 d . . . O11 O 0.8352(6) 0.5474(5) 0.5386(4) 0.0165(10) Uani 1 1 d . . . O12 O 0.9804(6) 0.4113(5) 0.6064(4) 0.0161(10) Uani 1 1 d . . . N1 N -0.2510(7) 0.5734(5) 0.2085(4) 0.0110(11) Uani 1 1 d . . . C1 C -0.1591(9) 0.6448(7) 0.1467(5) 0.0137(14) Uani 1 1 d . . . C2 C -0.1710(12) 0.5874(8) 0.0451(6) 0.0292(19) Uani 1 1 d . . . H2 H -0.1068 0.6369 0.0027 0.035 Uiso 1 1 calc R . . C3 C -0.2796(13) 0.4556(8) 0.0075(6) 0.035(2) Uani 1 1 d . . . H3 H -0.2894 0.4157 -0.0604 0.042 Uiso 1 1 calc R . . C4 C -0.3724(12) 0.3850(7) 0.0719(6) 0.0261(18) Uani 1 1 d . . . H4 H -0.4466 0.2967 0.0479 0.031 Uiso 1 1 calc R . . C5 C -0.3544(9) 0.4465(7) 0.1729(5) 0.0151(14) Uani 1 1 d . . . C6 C -0.0451(9) 0.7851(7) 0.1980(6) 0.0159(14) Uani 1 1 d . . . C7 C -0.4454(9) 0.3777(6) 0.2529(5) 0.0130(13) Uani 1 1 d . . . C8 C 0.6097(9) 0.9230(6) 0.3441(5) 0.0128(14) Uani 1 1 d . . . C9 C 0.4856(9) 0.7975(7) 0.2607(5) 0.0165(15) Uani 1 1 d . . . C10 C 0.4053(9) 0.9722(7) -0.0383(5) 0.0159(14) Uani 1 1 d . . . C11 C 0.9459(8) 0.4880(6) 0.5422(5) 0.0113(13) Uani 1 1 d . . . O13 O 0.1100(8) 1.1350(6) 0.1106(5) 0.0363(15) Uani 1 1 d . . . H1W H 0.0332 1.0758 0.0631 0.054 Uiso 1 1 d R . . H2W H 0.0587 1.1618 0.1541 0.054 Uiso 1 1 d R . . O14 O 0.2193(7) 1.0604(6) 0.3371(4) 0.0258(12) Uani 1 1 d . . . H3W H 0.1459 0.9893 0.3426 0.039 Uiso 1 1 d R . . H4W H 0.2572 1.1148 0.3936 0.039 Uiso 1 1 d R . . O15 O 1.0142(7) 0.8291(5) 0.5381(4) 0.0210(11) Uani 1 1 d . . . H5W H 1.0681 0.8963 0.5156 0.031 Uiso 1 1 d R . . H6W H 1.0552 0.8315 0.6031 0.031 Uiso 1 1 d R . . O16 O 0.5907(7) 0.6853(5) 0.5128(4) 0.0209(11) Uani 1 1 d . . . H7W H 0.4879 0.6715 0.4773 0.031 Uiso 1 1 d R . . H8W H 0.5940 0.6532 0.5696 0.031 Uiso 1 1 d R . . O17 O 0.3537(7) 0.8073(5) 0.4608(4) 0.0258(12) Uani 1 1 d . . . H9W H 0.3645 0.8667 0.4213 0.039 Uiso 1 1 d R . . H10W H 0.2479 0.7606 0.4515 0.039 Uiso 1 1 d R . . O18 O 0.0840(16) 0.7581(10) 0.7320(8) 0.138(6) Uani 1 1 d . . . H12W H 0.1723 0.8108 0.7790 0.207 Uiso 1 1 d R . . H11W H 0.0152 0.7007 0.7581 0.207 Uiso 1 1 d R . . O19 O 0.8443(14) 0.5401(12) 0.7772(7) 0.109(5) Uani 1 1 d . . . H14W H 0.7378 0.4917 0.7649 0.163 Uiso 1 1 d R . . H13W H 0.9067 0.4961 0.7608 0.163 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Yb1 0.01775(18) 0.01580(17) 0.01514(18) 0.00082(12) 0.00337(12) 0.00484(13) Yb2 0.01586(18) 0.01557(18) 0.01520(18) 0.00112(12) 0.00325(13) 0.00536(13) O1 0.022(3) 0.017(2) 0.022(3) 0.003(2) 0.013(2) -0.004(2) O2 0.023(3) 0.014(2) 0.010(2) -0.0033(18) 0.007(2) -0.001(2) O3 0.024(3) 0.012(2) 0.014(2) 0.0013(19) 0.010(2) -0.002(2) O4 0.033(3) 0.009(2) 0.032(3) -0.001(2) 0.009(3) 0.000(2) O5 0.020(3) 0.012(2) 0.011(2) -0.0020(18) -0.0004(19) 0.007(2) O6 0.012(2) 0.016(2) 0.013(2) -0.0016(19) -0.0045(19) 0.0030(19) O7 0.015(2) 0.012(2) 0.021(3) -0.0024(19) -0.004(2) 0.0053(19) O8 0.030(3) 0.014(2) 0.026(3) -0.008(2) -0.018(2) 0.012(2) O9 0.017(3) 0.035(3) 0.006(2) -0.008(2) 0.0004(19) 0.003(2) O10 0.011(2) 0.037(3) 0.009(2) -0.002(2) 0.0034(19) 0.008(2) O11 0.017(3) 0.019(2) 0.021(3) 0.008(2) 0.010(2) 0.013(2) O12 0.021(3) 0.018(2) 0.015(2) 0.011(2) 0.010(2) 0.010(2) N1 0.010(3) 0.011(3) 0.012(3) 0.000(2) 0.005(2) 0.002(2) C1 0.018(4) 0.013(3) 0.012(3) 0.000(3) 0.009(3) 0.005(3) C2 0.038(5) 0.029(4) 0.014(4) -0.001(3) 0.014(3) -0.003(4) C3 0.056(6) 0.030(4) 0.012(4) -0.008(3) 0.011(4) 0.006(4) C4 0.043(5) 0.013(3) 0.012(4) -0.009(3) 0.004(3) 0.000(3) C5 0.020(4) 0.013(3) 0.013(3) 0.002(3) 0.004(3) 0.006(3) C6 0.011(3) 0.015(3) 0.022(4) 0.004(3) 0.006(3) 0.004(3) C7 0.011(3) 0.014(3) 0.011(3) 0.000(3) -0.001(3) 0.004(3) C8 0.013(3) 0.012(3) 0.011(3) -0.003(3) 0.003(3) 0.000(3) C9 0.012(3) 0.016(4) 0.015(4) -0.007(3) -0.002(3) 0.002(3) C10 0.018(4) 0.015(3) 0.011(3) 0.003(3) 0.001(3) 0.004(3) C11 0.008(3) 0.013(3) 0.010(3) -0.003(3) 0.003(3) 0.000(3) O13 0.032(3) 0.035(3) 0.042(4) 0.006(3) -0.004(3) 0.020(3) O14 0.024(3) 0.030(3) 0.019(3) -0.009(2) 0.012(2) 0.001(2) O15 0.021(3) 0.017(2) 0.016(3) 0.000(2) -0.004(2) 0.001(2) O16 0.020(3) 0.033(3) 0.017(3) 0.011(2) 0.012(2) 0.013(2) O17 0.020(3) 0.025(3) 0.034(3) 0.004(2) 0.011(2) 0.008(2) O18 0.140(10) 0.076(7) 0.078(7) 0.043(6) -0.080(7) -0.061(7) O19 0.083(7) 0.147(10) 0.037(5) -0.014(5) 0.024(5) -0.046(7) _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 Yb1 O4 2.298(5) 1_665 ? Yb1 O14 2.359(5) . ? Yb1 O8 2.365(5) . ? Yb1 O1 2.389(5) . ? Yb1 O10 2.406(5) . ? Yb1 O5 2.443(5) . ? Yb1 O9 2.458(5) 2_675 ? Yb1 O13 2.460(5) . ? Yb1 C9 3.192(7) . ? Yb1 H3W 2.7531 . ? Yb2 O15 2.412(5) . ? Yb2 O16 2.415(5) . ? Yb2 O7 2.425(5) . ? Yb2 O2 2.432(5) 1_655 ? Yb2 O3 2.432(5) 1_655 ? Yb2 O12 2.453(5) 2_766 ? Yb2 O11 2.453(5) . ? Yb2 O6 2.533(5) . ? Yb2 N1 2.538(5) 1_655 ? O1 C6 1.245(8) . ? O2 C6 1.267(9) . ? O2 Yb2 2.432(5) 1_455 ? O3 C7 1.247(8) . ? O3 Yb2 2.432(5) 1_455 ? O4 C7 1.238(8) . ? O4 Yb1 2.298(5) 1_445 ? O5 C8 1.247(8) . ? O6 C8 1.241(8) . ? O7 C9 1.245(8) . ? O8 C9 1.246(8) . ? O9 C10 1.249(9) . ? O9 Yb1 2.458(5) 2_675 ? O10 C10 1.242(9) . ? O11 C11 1.245(8) . ? O12 C11 1.251(8) . ? O12 Yb2 2.453(5) 2_766 ? N1 C5 1.332(9) . ? N1 C1 1.344(9) . ? N1 Yb2 2.538(5) 1_455 ? C1 C2 1.389(10) . ? C1 C6 1.500(9) . ? C2 C3 1.386(11) . ? C2 H2 0.9300 . ? C3 C4 1.370(12) . ? C3 H3 0.9300 . ? C4 C5 1.385(10) . ? C4 H4 0.9300 . ? C5 C7 1.520(10) . ? C8 C9 1.564(9) . ? C10 C10 1.551(13) 2_675 ? C11 C11 1.556(12) 2_766 ? O13 H1W 0.8359 . ? O13 H2W 0.8601 . ? O14 H3W 0.8268 . ? O14 H4W 0.8353 . ? O15 H5W 0.8272 . ? O15 H6W 0.8333 . ? O16 H7W 0.8263 . ? O16 H8W 0.8358 . ? O17 H9W 0.8362 . ? O17 H10W 0.8331 . ? O18 H12W 0.8451 . ? O18 H11W 0.8439 . ? O19 H14W 0.8381 . ? O19 H13W 0.8395 . ? 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 Yb1 O14 83.7(2) 1_665 . ? O4 Yb1 O8 146.1(2) 1_665 . ? O14 Yb1 O8 105.7(2) . . ? O4 Yb1 O1 142.25(19) 1_665 . ? O14 Yb1 O1 76.44(18) . . ? O8 Yb1 O1 71.12(19) . . ? O4 Yb1 O10 105.34(19) 1_665 . ? O14 Yb1 O10 150.47(18) . . ? O8 Yb1 O10 82.65(19) . . ? O1 Yb1 O10 79.88(17) . . ? O4 Yb1 O5 83.75(18) 1_665 . ? O14 Yb1 O5 76.87(18) . . ? O8 Yb1 O5 67.49(15) . . ? O1 Yb1 O5 121.34(17) . . ? O10 Yb1 O5 131.37(16) . . ? O4 Yb1 O9 75.61(19) 1_665 2_675 ? O14 Yb1 O9 142.74(17) . 2_675 ? O8 Yb1 O9 78.0(2) . 2_675 ? O1 Yb1 O9 136.51(17) . 2_675 ? O10 Yb1 O9 66.24(16) . 2_675 ? O5 Yb1 O9 70.44(16) . 2_675 ? O4 Yb1 O13 71.7(2) 1_665 . ? O14 Yb1 O13 80.6(2) . . ? O8 Yb1 O13 141.35(19) . . ? O1 Yb1 O13 73.6(2) . . ? O10 Yb1 O13 75.98(19) . . ? O5 Yb1 O13 148.21(18) . . ? O9 Yb1 O13 120.1(2) 2_675 . ? O4 Yb1 C9 128.93(19) 1_665 . ? O14 Yb1 C9 97.71(19) . . ? O8 Yb1 C9 19.53(17) . . ? O1 Yb1 C9 85.82(18) . . ? O10 Yb1 C9 97.89(17) . . ? O5 Yb1 C9 47.96(15) . . ? O9 Yb1 C9 73.32(19) 2_675 . ? O13 Yb1 C9 159.24(19) . . ? O4 Yb1 H3W 99.9 1_665 . ? O14 Yb1 H3W 16.4 . . ? O8 Yb1 H3W 93.1 . . ? O1 Yb1 H3W 61.7 . . ? O10 Yb1 H3W 140.4 . . ? O5 Yb1 H3W 80.9 . . ? O9 Yb1 H3W 151.3 2_675 . ? O13 Yb1 H3W 83.8 . . ? C9 Yb1 H3W 89.1 . . ? O15 Yb2 O16 85.17(18) . . ? O15 Yb2 O7 136.71(16) . . ? O16 Yb2 O7 78.91(17) . . ? O15 Yb2 O2 80.17(17) . 1_655 ? O16 Yb2 O2 141.95(17) . 1_655 ? O7 Yb2 O2 88.11(17) . 1_655 ? O15 Yb2 O3 143.87(17) . 1_655 ? O16 Yb2 O3 83.32(17) . 1_655 ? O7 Yb2 O3 73.82(16) . 1_655 ? O2 Yb2 O3 127.24(15) 1_655 1_655 ? O15 Yb2 O12 78.39(17) . 2_766 ? O16 Yb2 O12 135.49(16) . 2_766 ? O7 Yb2 O12 138.33(16) . 2_766 ? O2 Yb2 O12 75.28(16) 1_655 2_766 ? O3 Yb2 O12 86.23(17) 1_655 2_766 ? O15 Yb2 O11 72.97(17) . . ? O16 Yb2 O11 69.94(16) . . ? O7 Yb2 O11 134.88(17) . . ? O2 Yb2 O11 136.02(16) 1_655 . ? O3 Yb2 O11 70.91(16) 1_655 . ? O12 Yb2 O11 65.75(15) 2_766 . ? O15 Yb2 O6 71.17(15) . . ? O16 Yb2 O6 71.05(17) . . ? O7 Yb2 O6 65.61(15) . . ? O2 Yb2 O6 71.00(16) 1_655 . ? O3 Yb2 O6 135.09(16) 1_655 . ? O12 Yb2 O6 137.54(16) 2_766 . ? O11 Yb2 O6 128.27(15) . . ? O15 Yb2 N1 135.90(18) . 1_655 ? O16 Yb2 N1 138.91(18) . 1_655 ? O7 Yb2 N1 69.11(17) . 1_655 ? O2 Yb2 N1 63.45(16) 1_655 1_655 ? O3 Yb2 N1 63.79(16) 1_655 1_655 ? O12 Yb2 N1 69.27(17) 2_766 1_655 ? O11 Yb2 N1 116.62(16) . 1_655 ? O6 Yb2 N1 115.09(16) . 1_655 ? C6 O1 Yb1 134.7(5) . . ? C6 O2 Yb2 126.0(4) . 1_455 ? C7 O3 Yb2 125.5(4) . 1_455 ? C7 O4 Yb1 172.0(5) . 1_445 ? C8 O5 Yb1 118.4(4) . . ? C8 O6 Yb2 118.6(4) . . ? C9 O7 Yb2 121.4(4) . . ? C9 O8 Yb1 121.1(4) . . ? C10 O9 Yb1 119.2(4) . 2_675 ? C10 O10 Yb1 120.5(4) . . ? C11 O11 Yb2 120.6(4) . . ? C11 O12 Yb2 120.6(4) . 2_766 ? C5 N1 C1 120.3(6) . . ? C5 N1 Yb2 119.7(4) . 1_455 ? C1 N1 Yb2 120.0(4) . 1_455 ? N1 C1 C2 120.5(6) . . ? N1 C1 C6 114.5(6) . . ? C2 C1 C6 125.0(6) . . ? C3 C2 C1 119.3(7) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C4 C3 C2 119.1(7) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.3(7) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 121.5(7) . . ? N1 C5 C7 114.2(6) . . ? C4 C5 C7 124.3(6) . . ? O1 C6 O2 125.7(6) . . ? O1 C6 C1 118.2(6) . . ? O2 C6 C1 116.1(6) . . ? O4 C7 O3 126.1(7) . . ? O4 C7 C5 117.3(6) . . ? O3 C7 C5 116.6(6) . . ? O6 C8 O5 127.6(6) . . ? O6 C8 C9 116.4(6) . . ? O5 C8 C9 116.1(6) . . ? O7 C9 O8 126.3(6) . . ? O7 C9 C8 117.2(6) . . ? O8 C9 C8 116.5(6) . . ? O7 C9 Yb1 165.4(5) . . ? O8 C9 Yb1 39.4(3) . . ? C8 C9 Yb1 77.2(4) . . ? O10 C10 O9 127.2(6) . . ? O10 C10 C10 117.1(7) . 2_675 ? O9 C10 C10 115.6(8) . 2_675 ? O11 C11 O12 127.3(6) . . ? O11 C11 C11 116.5(7) . 2_766 ? O12 C11 C11 116.2(7) . 2_766 ? Yb1 O13 H1W 104.9 . . ? Yb1 O13 H2W 115.2 . . ? H1W O13 H2W 108.7 . . ? Yb1 O14 H3W 110.0 . . ? Yb1 O14 H4W 134.8 . . ? H3W O14 H4W 111.8 . . ? Yb2 O15 H5W 110.1 . . ? Yb2 O15 H6W 137.3 . . ? H5W O15 H6W 112.6 . . ? Yb2 O16 H7W 109.7 . . ? Yb2 O16 H8W 126.5 . . ? H7W O16 H8W 112.1 . . ? H9W O17 H10W 111.8 . . ? H12W O18 H11W 112.4 . . ? H14W O19 H13W 111.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Yb1 O1 C6 -95.4(7) 1_665 . . . ? O14 Yb1 O1 C6 -35.2(6) . . . . ? O8 Yb1 O1 C6 77.0(7) . . . . ? O10 Yb1 O1 C6 162.6(7) . . . . ? O5 Yb1 O1 C6 30.0(7) . . . . ? O9 Yb1 O1 C6 124.1(6) 2_675 . . . ? O13 Yb1 O1 C6 -119.2(7) . . . . ? C9 Yb1 O1 C6 63.8(6) . . . . ? O4 Yb1 O5 C8 -157.5(5) 1_665 . . . ? O14 Yb1 O5 C8 117.6(5) . . . . ? O8 Yb1 O5 C8 4.2(5) . . . . ? O1 Yb1 O5 C8 52.7(5) . . . . ? O10 Yb1 O5 C8 -52.5(6) . . . . ? O9 Yb1 O5 C8 -80.6(5) 2_675 . . . ? O13 Yb1 O5 C8 163.6(5) . . . . ? C9 Yb1 O5 C8 4.3(5) . . . . ? O15 Yb2 O6 C8 178.8(5) . . . . ? O16 Yb2 O6 C8 -89.9(5) . . . . ? O7 Yb2 O6 C8 -3.8(5) . . . . ? O2 Yb2 O6 C8 93.0(5) 1_655 . . . ? O3 Yb2 O6 C8 -31.1(6) 1_655 . . . ? O12 Yb2 O6 C8 132.2(5) 2_766 . . . ? O11 Yb2 O6 C8 -132.8(5) . . . . ? N1 Yb2 O6 C8 46.1(5) 1_655 . . . ? O15 Yb2 O7 C9 11.4(7) . . . . ? O16 Yb2 O7 C9 82.0(5) . . . . ? O2 Yb2 O7 C9 -62.1(5) 1_655 . . . ? O3 Yb2 O7 C9 168.1(6) 1_655 . . . ? O12 Yb2 O7 C9 -127.3(5) 2_766 . . . ? O11 Yb2 O7 C9 128.4(5) . . . . ? O6 Yb2 O7 C9 7.9(5) . . . . ? N1 Yb2 O7 C9 -124.3(6) 1_655 . . . ? O4 Yb1 O8 C9 34.4(8) 1_665 . . . ? O14 Yb1 O8 C9 -67.9(6) . . . . ? O1 Yb1 O8 C9 -137.2(6) . . . . ? O10 Yb1 O8 C9 141.1(6) . . . . ? O5 Yb1 O8 C9 0.3(6) . . . . ? O9 Yb1 O8 C9 73.9(6) 2_675 . . . ? O13 Yb1 O8 C9 -162.5(5) . . . . ? O4 Yb1 O10 C10 75.9(5) 1_665 . . . ? O14 Yb1 O10 C10 -179.5(5) . . . . ? O8 Yb1 O10 C10 -70.4(5) . . . . ? O1 Yb1 O10 C10 -142.5(5) . . . . ? O5 Yb1 O10 C10 -19.3(6) . . . . ? O9 Yb1 O10 C10 9.6(5) 2_675 . . . ? O13 Yb1 O10 C10 142.0(6) . . . . ? C9 Yb1 O10 C10 -58.2(5) . . . . ? O15 Yb2 O11 C11 -89.9(5) . . . . ? O16 Yb2 O11 C11 179.1(5) . . . . ? O7 Yb2 O11 C11 129.8(5) . . . . ? O2 Yb2 O11 C11 -35.0(6) 1_655 . . . ? O3 Yb2 O11 C11 89.3(5) 1_655 . . . ? O12 Yb2 O11 C11 -5.2(5) 2_766 . . . ? O6 Yb2 O11 C11 -137.7(4) . . . . ? N1 Yb2 O11 C11 43.5(5) 1_655 . . . ? C5 N1 C1 C2 0.2(10) . . . . ? Yb2 N1 C1 C2 178.8(6) 1_455 . . . ? C5 N1 C1 C6 -178.7(6) . . . . ? Yb2 N1 C1 C6 0.0(8) 1_455 . . . ? N1 C1 C2 C3 0.3(13) . . . . ? C6 C1 C2 C3 179.0(8) . . . . ? C1 C2 C3 C4 -0.2(14) . . . . ? C2 C3 C4 C5 -0.5(14) . . . . ? C1 N1 C5 C4 -0.9(10) . . . . ? Yb2 N1 C5 C4 -179.5(6) 1_455 . . . ? C1 N1 C5 C7 178.3(6) . . . . ? Yb2 N1 C5 C7 -0.4(7) 1_455 . . . ? C3 C4 C5 N1 1.0(12) . . . . ? C3 C4 C5 C7 -178.0(7) . . . . ? Yb1 O1 C6 O2 33.7(11) . . . . ? Yb1 O1 C6 C1 -145.7(5) . . . . ? Yb2 O2 C6 O1 179.7(5) 1_455 . . . ? Yb2 O2 C6 C1 -0.9(8) 1_455 . . . ? N1 C1 C6 O1 -180.0(6) . . . . ? C2 C1 C6 O1 1.2(11) . . . . ? N1 C1 C6 O2 0.6(9) . . . . ? C2 C1 C6 O2 -178.2(7) . . . . ? Yb1 O4 C7 O3 -87(4) 1_445 . . . ? Yb1 O4 C7 C5 93(4) 1_445 . . . ? Yb2 O3 C7 O4 175.1(5) 1_455 . . . ? Yb2 O3 C7 C5 -4.9(8) 1_455 . . . ? N1 C5 C7 O4 -176.8(6) . . . . ? C4 C5 C7 O4 2.3(10) . . . . ? N1 C5 C7 O3 3.3(9) . . . . ? C4 C5 C7 O3 -177.7(7) . . . . ? Yb2 O6 C8 O5 179.9(5) . . . . ? Yb2 O6 C8 C9 0.4(8) . . . . ? Yb1 O5 C8 O6 173.3(6) . . . . ? Yb1 O5 C8 C9 -7.3(8) . . . . ? Yb2 O7 C9 O8 168.9(6) . . . . ? Yb2 O7 C9 C8 -10.7(9) . . . . ? Yb2 O7 C9 Yb1 177.5(17) . . . . ? Yb1 O8 C9 O7 176.6(6) . . . . ? Yb1 O8 C9 C8 -3.7(9) . . . . ? O6 C8 C9 O7 6.6(10) . . . . ? O5 C8 C9 O7 -172.9(6) . . . . ? O6 C8 C9 O8 -173.0(6) . . . . ? O5 C8 C9 O8 7.4(10) . . . . ? O6 C8 C9 Yb1 -175.5(6) . . . . ? O5 C8 C9 Yb1 5.0(5) . . . . ? O4 Yb1 C9 O7 -167(2) 1_665 . . . ? O14 Yb1 C9 O7 105(2) . . . . ? O8 Yb1 C9 O7 -10.9(18) . . . . ? O1 Yb1 C9 O7 29(2) . . . . ? O10 Yb1 C9 O7 -50(2) . . . . ? O5 Yb1 C9 O7 169(2) . . . . ? O9 Yb1 C9 O7 -112(2) 2_675 . . . ? O13 Yb1 C9 O7 21(2) . . . . ? O4 Yb1 C9 O8 -156.1(6) 1_665 . . . ? O14 Yb1 C9 O8 115.9(6) . . . . ? O1 Yb1 C9 O8 40.2(6) . . . . ? O10 Yb1 C9 O8 -39.0(6) . . . . ? O5 Yb1 C9 O8 -179.7(7) . . . . ? O9 Yb1 C9 O8 -101.2(6) 2_675 . . . ? O13 Yb1 C9 O8 32.1(10) . . . . ? O4 Yb1 C9 C8 20.5(5) 1_665 . . . ? O14 Yb1 C9 C8 -67.6(4) . . . . ? O8 Yb1 C9 C8 176.6(8) . . . . ? O1 Yb1 C9 C8 -143.3(4) . . . . ? O10 Yb1 C9 C8 137.6(4) . . . . ? O5 Yb1 C9 C8 -3.1(3) . . . . ? O9 Yb1 C9 C8 75.3(4) 2_675 . . . ? O13 Yb1 C9 C8 -151.3(5) . . . . ? Yb1 O10 C10 O9 171.0(6) . . . . ? Yb1 O10 C10 C10 -9.2(10) . . . 2_675 ? Yb1 O9 C10 O10 171.2(6) 2_675 . . . ? Yb1 O9 C10 C10 -8.6(10) 2_675 . . 2_675 ? Yb2 O11 C11 O12 -175.2(5) . . . . ? Yb2 O11 C11 C11 5.0(9) . . . 2_766 ? Yb2 O12 C11 O11 -175.1(5) 2_766 . . . ? Yb2 O12 C11 C11 4.7(9) 2_766 . . 2_766 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H1W O10 0.84 2.39 3.005(8) 131.4 2_575 O13 H2W O18 0.86 2.35 3.209(18) 177.4 2_576 O14 H3W O2 0.83 1.95 2.731(7) 156.4 . O14 H4W O16 0.84 2.20 2.967(8) 152.4 2_676 O14 H4W O6 0.84 2.60 3.240(7) 134.2 2_676 O15 H5W O6 0.83 2.20 2.835(7) 134.3 2_776 O15 H6W O18 0.83 1.90 2.675(10) 154.9 1_655 O16 H7W O17 0.83 2.05 2.634(7) 127.1 . O16 H8W O3 0.84 2.15 2.843(7) 140.6 2_566 O17 H9W O5 0.84 2.49 3.222(7) 146.3 . O17 H10W O12 0.83 2.11 2.894(7) 156.0 2_666 O17 H10W O15 0.83 2.68 3.235(7) 125.1 1_455 O18 H11W O11 0.84 2.99 3.094(10) 88.8 1_455 O18 H11W O13 0.84 2.91 3.209(18) 103.1 2_576 O19 H13W O12 0.84 2.42 3.117(12) 140.6 . O19 H14W O7 0.84 2.27 3.076(10) 162.5 2_666 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.841 _refine_diff_density_min -0.967 _refine_diff_density_rms 0.212