# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'La-Sheng Long' 'Rong-Bin Huang' 'Xiang-Jian Kong' 'Yan-Ping Ren' 'Lan-Sun Zheng' 'Gui-Lin Zhuang' _publ_contact_author_name 'La-Sheng Long' _publ_contact_author_email LSLONG@XMU.EDU.CN _publ_section_title ; In Situ Cyclodehydration of Iminodiacetic acid into 2,5-Diketopiperazine-1,4-diacetate in the Lanthanide-Based Coordination Ploymers ; # Attachment 'complex_12.cif' data_complex_1 _database_code_depnum_ccdc_archive 'CCDC 708190' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Dy2 N2 O16' _chemical_formula_weight 765.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Dy Dy -0.1892 4.4098 '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 6.7426(16) _cell_length_b 7.8105(18) _cell_length_c 9.168(2) _cell_angle_alpha 95.603(4) _cell_angle_beta 110.399(4) _cell_angle_gamma 93.470(4) _cell_volume 448.06(18) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3012 _cell_measurement_theta_min 2.390 _cell_measurement_theta_max 28.257 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.836 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 358 _exptl_absorpt_coefficient_mu 8.370 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4882 _exptl_absorpt_correction_T_max 0.7873 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex 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 3425 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1725 _reflns_number_gt 1705 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXTL-Plus (Sheldrick, 1990)' _computing_cell_refinement 'SHELXTL-Plus (Sheldrick, 1990)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V.5.0 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0263P)^2^+0.6029P] 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 1725 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0222 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0511 _refine_ls_wR_factor_gt 0.0508 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Dy1 Dy 0.380903(19) 0.767933(17) 0.216983(15) 0.01489(4) Uani 1 1 d . . . O1 O 0.7212(4) 0.4270(3) 0.6383(3) 0.0393(6) Uani 1 1 d . . . O2 O 0.7498(4) 1.0370(3) 0.6458(3) 0.0277(6) Uani 1 1 d . . . O3 O 0.6720(4) 0.8461(3) 0.4364(3) 0.0334(7) Uani 1 1 d . . . O4 O 0.7185(3) 1.0052(3) -0.0591(3) 0.0271(5) Uani 1 1 d . . . O5 O 0.6599(3) 0.8729(3) 0.1286(3) 0.0285(6) Uani 1 1 d . . . O6 O 0.7068(4) 0.3687(3) 0.0465(3) 0.0296(6) Uani 1 1 d . . . O7 O 0.5807(4) 0.5286(3) 0.2033(2) 0.0252(6) Uani 1 1 d . . . C1 C 0.8522(5) 0.4670(4) 0.5754(4) 0.0258(8) Uani 1 1 d . . . C2 C 1.0916(6) 0.6740(4) 0.5203(4) 0.0322(8) Uani 1 1 d . . . H2A H 1.2214 0.7261 0.6031 0.039 Uiso 1 1 calc R . . H2B H 1.0358 0.7622 0.4539 0.039 Uiso 1 1 calc R . . C3 C 0.8856(5) 0.7678(4) 0.6824(4) 0.0267(8) Uani 1 1 d . . . H3A H 1.0158 0.8303 0.7570 0.032 Uiso 1 1 calc R . . H3B H 0.8047 0.7211 0.7413 0.032 Uiso 1 1 calc R . . C4 C 0.7572(5) 0.8921(4) 0.5791(4) 0.0188(7) Uani 1 1 d . . . C5 C 0.6100(5) 0.9650(4) 0.0197(4) 0.0194(7) Uani 1 1 d . . . C6 C 0.5829(5) 0.4700(4) 0.0725(4) 0.0202(7) Uani 1 1 d . . . N1 N 0.9389(4) 0.6254(3) 0.5917(3) 0.0229(6) Uani 1 1 d . . . O1W O 0.0014(4) 0.7095(4) 0.0918(3) 0.0419(8) Uani 1 1 d . . . H1WA H -0.0454 0.6099 0.1026 0.050 Uiso 1 1 d R . . H1WB H -0.0545 0.7913 0.1263 0.050 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 Dy1 0.01770(6) 0.01385(7) 0.01580(6) 0.00211(5) 0.00876(5) 0.00453(5) O1 0.0557(12) 0.0276(13) 0.0630(13) 0.0204(10) 0.0506(10) 0.0169(11) O2 0.0391(11) 0.0208(11) 0.0289(11) 0.0005(9) 0.0184(9) 0.0125(10) O3 0.0301(12) 0.0428(15) 0.0211(12) -0.0023(11) 0.0016(10) 0.0136(11) O4 0.0282(10) 0.0284(12) 0.0376(11) 0.0171(9) 0.0228(9) 0.0118(9) O5 0.0209(10) 0.0361(13) 0.0335(11) 0.0198(10) 0.0108(9) 0.0097(10) O6 0.0266(10) 0.0353(13) 0.0254(11) -0.0022(10) 0.0065(9) 0.0177(10) O7 0.0357(11) 0.0258(12) 0.0179(10) 0.0021(9) 0.0129(9) 0.0127(10) C1 0.0337(14) 0.0227(16) 0.0333(15) 0.0145(13) 0.0223(12) 0.0154(13) C2 0.0438(16) 0.0159(15) 0.0523(19) 0.0083(14) 0.0345(14) 0.0078(14) C3 0.0405(17) 0.0248(17) 0.0205(14) 0.0029(12) 0.0163(12) 0.0135(14) C4 0.0170(12) 0.0213(15) 0.0219(14) 0.0033(12) 0.0109(11) 0.0051(12) C5 0.0193(13) 0.0154(14) 0.0264(14) 0.0054(12) 0.0107(11) 0.0038(12) C6 0.0225(13) 0.0162(14) 0.0235(14) 0.0011(12) 0.0103(12) 0.0033(12) N1 0.0328(12) 0.0178(13) 0.0286(12) 0.0099(10) 0.0205(10) 0.0129(10) O1W 0.0258(11) 0.0416(15) 0.0588(16) -0.0116(13) 0.0213(11) -0.0019(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Dy1 O3 2.266(2) . ? Dy1 O2 2.289(2) 2_676 ? Dy1 O1 2.336(3) 2_666 ? Dy1 O4 2.378(2) 2_675 ? Dy1 O7 2.388(2) . ? Dy1 O6 2.397(2) 2_665 ? Dy1 O1W 2.405(2) . ? Dy1 O5 2.423(3) . ? O1 C1 1.251(4) . ? O1 Dy1 2.336(3) 2_666 ? O2 C4 1.245(4) . ? O2 Dy1 2.289(2) 2_676 ? O3 C4 1.236(4) . ? O4 C5 1.241(4) . ? O4 Dy1 2.378(2) 2_675 ? O5 C5 1.251(4) . ? O6 C6 1.250(4) . ? O6 Dy1 2.397(2) 2_665 ? O7 C6 1.246(4) . ? C1 N1 1.308(4) . ? C1 C2 1.490(5) 2_766 ? C2 N1 1.451(5) . ? C2 C1 1.490(5) 2_766 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.461(4) . ? C3 C4 1.517(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C5 1.547(6) 2_675 ? C6 C6 1.544(6) 2_665 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Dy1 O2 79.27(9) . 2_676 ? O3 Dy1 O1 85.79(10) . 2_666 ? O2 Dy1 O1 83.16(9) 2_676 2_666 ? O3 Dy1 O4 113.32(9) . 2_675 ? O2 Dy1 O4 74.28(9) 2_676 2_675 ? O1 Dy1 O4 146.41(9) 2_666 2_675 ? O3 Dy1 O7 80.02(8) . . ? O2 Dy1 O7 151.37(8) 2_676 . ? O1 Dy1 O7 75.80(9) 2_666 . ? O4 Dy1 O7 132.65(8) 2_675 . ? O3 Dy1 O6 139.04(9) . 2_665 ? O2 Dy1 O6 138.92(8) 2_676 2_665 ? O1 Dy1 O6 108.74(9) 2_666 2_665 ? O4 Dy1 O6 75.51(8) 2_675 2_665 ? O7 Dy1 O6 67.66(8) . 2_665 ? O3 Dy1 O1W 150.10(10) . . ? O2 Dy1 O1W 76.09(9) 2_676 . ? O1 Dy1 O1W 74.78(10) 2_666 . ? O4 Dy1 O1W 75.83(9) 2_675 . ? O7 Dy1 O1W 115.70(9) . . ? O6 Dy1 O1W 69.99(9) 2_665 . ? O3 Dy1 O5 73.94(9) . . ? O2 Dy1 O5 118.07(9) 2_676 . ? O1 Dy1 O5 146.15(8) 2_666 . ? O4 Dy1 O5 67.44(8) 2_675 . ? O7 Dy1 O5 74.21(8) . . ? O6 Dy1 O5 73.54(8) 2_665 . ? O1W Dy1 O5 133.26(9) . . ? C1 O1 Dy1 146.1(2) . 2_666 ? C4 O2 Dy1 155.0(2) . 2_676 ? C4 O3 Dy1 151.7(2) . . ? C5 O4 Dy1 118.7(2) . 2_675 ? C5 O5 Dy1 117.46(19) . . ? C6 O6 Dy1 117.72(19) . 2_665 ? C6 O7 Dy1 118.2(2) . . ? O1 C1 N1 122.4(3) . . ? O1 C1 C2 117.4(3) . 2_766 ? N1 C1 C2 120.2(3) . 2_766 ? N1 C2 C1 116.7(3) . 2_766 ? N1 C2 H2A 108.1 . . ? C1 C2 H2A 108.1 2_766 . ? N1 C2 H2B 108.1 . . ? C1 C2 H2B 108.1 2_766 . ? H2A C2 H2B 107.3 . . ? N1 C3 C4 112.2(3) . . ? N1 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? O3 C4 O2 124.6(3) . . ? O3 C4 C3 119.0(3) . . ? O2 C4 C3 116.4(3) . . ? O4 C5 O5 126.7(3) . . ? O4 C5 C5 117.3(4) . 2_675 ? O5 C5 C5 116.0(4) . 2_675 ? O7 C6 O6 126.7(3) . . ? O7 C6 C6 116.7(4) . 2_665 ? O6 C6 C6 116.6(4) . 2_665 ? C1 N1 C2 123.1(3) . . ? C1 N1 C3 121.9(3) . . ? C2 N1 C3 115.0(3) . . ? Dy1 O1W H1WA 113.0 . . ? Dy1 O1W H1WB 107.5 . . ? H1WA O1W H1WB 113.4 . . ? 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 O1W H1WB O5 0.85 2.07 2.803(4) 143.9 1_455 O1W H1WB O4 0.85 2.66 3.194(4) 122.2 1_455 O1W H1WA O6 0.85 2.33 3.126(4) 155.9 1_455 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.135 _refine_diff_density_min -0.977 _refine_diff_density_rms 0.134 # Attachment 'complex_22.cif' data_complex_2 _database_code_depnum_ccdc_archive 'CCDC 708191' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Ho2 N2 O16' _chemical_formula_weight 770.10 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' Ho Ho -0.2175 4.6783 '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 6.6964(15) _cell_length_b 7.7827(18) _cell_length_c 9.126(2) _cell_angle_alpha 95.692(4) _cell_angle_beta 110.274(3) _cell_angle_gamma 93.543(4) _cell_volume 441.57(17) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3545 _cell_measurement_theta_min 2.499 _cell_measurement_theta_max 28.247 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.896 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 8.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2539 _exptl_absorpt_correction_T_max 0.3272 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex 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 3329 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1680 _reflns_number_gt 1655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXTL-Plus (Sheldrick, 1990)' _computing_cell_refinement 'SHELXTL-Plus (Sheldrick, 1990)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V.5.0 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0320P)^2^+0.0675P] 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 1680 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0525 _refine_ls_wR_factor_gt 0.0521 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ho1 Ho 0.381638(15) 0.768184(12) 0.216900(11) 0.01403(4) Uani 1 1 d . . . O1 O 0.7192(3) 0.4265(3) 0.6387(3) 0.0369(5) Uani 1 1 d . . . O2 O 0.7495(3) 1.0383(2) 0.6459(2) 0.0282(5) Uani 1 1 d . . . O3 O 0.6727(3) 0.8469(3) 0.4350(2) 0.0317(6) Uani 1 1 d . . . O4 O 0.7196(3) 1.0058(2) -0.0596(2) 0.0254(5) Uani 1 1 d . . . O5 O 0.6616(3) 0.8739(3) 0.1295(2) 0.0274(5) Uani 1 1 d . . . O6 O 0.7062(3) 0.3680(3) 0.0462(2) 0.0284(5) Uani 1 1 d . . . O7 O 0.5822(3) 0.5301(2) 0.2040(2) 0.0253(5) Uani 1 1 d . . . C1 C 0.8500(4) 0.4662(4) 0.5754(3) 0.0248(6) Uani 1 1 d . . . C2 C 1.0939(5) 0.6749(4) 0.5221(4) 0.0314(7) Uani 1 1 d . . . H2A H 1.2242 0.7254 0.6065 0.038 Uiso 1 1 calc R . . H2B H 1.0403 0.7650 0.4568 0.038 Uiso 1 1 calc R . . C3 C 0.8822(5) 0.7670(3) 0.6812(4) 0.0263(7) Uani 1 1 d . . . H3A H 1.0123 0.8293 0.7577 0.032 Uiso 1 1 calc R . . H3B H 0.7986 0.7193 0.7386 0.032 Uiso 1 1 calc R . . C4 C 0.7560(4) 0.8926(3) 0.5787(3) 0.0177(6) Uani 1 1 d . . . C5 C 0.6096(4) 0.9651(3) 0.0192(3) 0.0195(6) Uani 1 1 d . . . C6 C 0.5838(4) 0.4703(3) 0.0732(3) 0.0191(6) Uani 1 1 d . . . N1 N 0.9380(4) 0.6256(3) 0.5913(3) 0.0228(5) Uani 1 1 d . . . O1W O 0.0036(3) 0.7095(3) 0.0931(3) 0.0411(6) Uani 1 1 d . . . H1WA H -0.0462 0.6102 0.1010 0.049 Uiso 1 1 d R . . H1WB H -0.0553 0.7917 0.1246 0.049 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 Ho1 0.01661(6) 0.01269(6) 0.01541(6) 0.00180(5) 0.00845(5) 0.00463(5) O1 0.0514(10) 0.0271(10) 0.0588(11) 0.0209(9) 0.0465(9) 0.0171(9) O2 0.0401(10) 0.0194(9) 0.0310(10) 0.0010(8) 0.0192(8) 0.0126(8) O3 0.0299(10) 0.0398(11) 0.0193(10) -0.0031(9) 0.0014(8) 0.0131(9) O4 0.0268(8) 0.0263(9) 0.0364(9) 0.0159(8) 0.0231(7) 0.0111(7) O5 0.0196(8) 0.0341(10) 0.0346(10) 0.0223(8) 0.0115(8) 0.0084(8) O6 0.0263(9) 0.0343(10) 0.0230(9) -0.0039(8) 0.0063(8) 0.0174(8) O7 0.0392(10) 0.0228(9) 0.0193(9) 0.0031(8) 0.0153(8) 0.0134(8) C1 0.0324(12) 0.0206(12) 0.0338(13) 0.0120(11) 0.0238(10) 0.0109(10) C2 0.0367(13) 0.0178(13) 0.0532(16) 0.0084(12) 0.0313(12) 0.0057(11) C3 0.0375(14) 0.0246(14) 0.0215(11) 0.0036(10) 0.0146(10) 0.0136(12) C4 0.0172(10) 0.0155(11) 0.0235(12) 0.0006(10) 0.0110(9) 0.0057(9) C5 0.0168(11) 0.0195(12) 0.0237(12) 0.0037(11) 0.0084(10) 0.0047(10) C6 0.0214(11) 0.0154(11) 0.0207(12) -0.0002(10) 0.0082(10) 0.0033(10) N1 0.0326(10) 0.0168(10) 0.0300(11) 0.0093(9) 0.0211(9) 0.0136(9) O1W 0.0243(9) 0.0446(13) 0.0520(14) -0.0137(11) 0.0169(9) -0.0023(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ho1 O3 2.2491(19) . ? Ho1 O2 2.272(2) 2_676 ? Ho1 O1 2.318(2) 2_666 ? Ho1 O4 2.364(2) 2_675 ? Ho1 O7 2.372(2) . ? Ho1 O1W 2.380(2) . ? Ho1 O6 2.382(2) 2_665 ? Ho1 O5 2.409(2) . ? O1 C1 1.245(4) . ? O1 Ho1 2.318(2) 2_666 ? O2 C4 1.245(3) . ? O2 Ho1 2.272(2) 2_676 ? O3 C4 1.238(3) . ? O4 C5 1.243(4) . ? O4 Ho1 2.364(2) 2_675 ? O5 C5 1.252(4) . ? O6 C6 1.244(4) . ? O6 Ho1 2.382(2) 2_665 ? O7 C6 1.241(3) . ? C1 N1 1.312(4) . ? C1 C2 1.493(4) 2_766 ? C2 N1 1.446(4) . ? C2 C1 1.493(4) 2_766 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.452(4) . ? C3 C4 1.510(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C5 1.534(5) 2_675 ? C6 C6 1.552(5) 2_665 ? O1W H1WA 0.8425 . ? O1W H1WB 0.8489 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Ho1 O2 79.37(8) . 2_676 ? O3 Ho1 O1 85.82(8) . 2_666 ? O2 Ho1 O1 83.17(8) 2_676 2_666 ? O3 Ho1 O4 113.38(8) . 2_675 ? O2 Ho1 O4 74.23(8) 2_676 2_675 ? O1 Ho1 O4 146.32(7) 2_666 2_675 ? O3 Ho1 O7 79.79(7) . . ? O2 Ho1 O7 151.06(7) 2_676 . ? O1 Ho1 O7 75.49(8) 2_666 . ? O4 Ho1 O7 133.05(7) 2_675 . ? O3 Ho1 O1W 150.18(9) . . ? O2 Ho1 O1W 75.97(8) 2_676 . ? O1 Ho1 O1W 74.90(9) 2_666 . ? O4 Ho1 O1W 75.60(8) 2_675 . ? O7 Ho1 O1W 115.87(8) . . ? O3 Ho1 O6 138.99(8) . 2_665 ? O2 Ho1 O6 138.86(7) 2_676 2_665 ? O1 Ho1 O6 108.74(8) 2_666 2_665 ? O4 Ho1 O6 75.49(7) 2_675 2_665 ? O7 Ho1 O6 67.98(7) . 2_665 ? O1W Ho1 O6 69.99(8) . 2_665 ? O3 Ho1 O5 73.57(8) . . ? O2 Ho1 O5 118.07(7) 2_676 . ? O1 Ho1 O5 145.89(7) 2_666 . ? O4 Ho1 O5 67.79(7) 2_675 . ? O7 Ho1 O5 74.31(7) . . ? O1W Ho1 O5 133.51(8) . . ? O6 Ho1 O5 73.79(7) 2_665 . ? C1 O1 Ho1 145.88(19) . 2_666 ? C4 O2 Ho1 154.5(2) . 2_676 ? C4 O3 Ho1 150.8(2) . . ? C5 O4 Ho1 118.27(17) . 2_675 ? C5 O5 Ho1 116.89(17) . . ? C6 O6 Ho1 118.09(17) . 2_665 ? C6 O7 Ho1 118.16(17) . . ? O1 C1 N1 122.5(3) . . ? O1 C1 C2 117.8(3) . 2_766 ? N1 C1 C2 119.7(3) . 2_766 ? N1 C2 C1 116.5(2) . 2_766 ? N1 C2 H2A 108.2 . . ? C1 C2 H2A 108.2 2_766 . ? N1 C2 H2B 108.2 . . ? C1 C2 H2B 108.2 2_766 . ? H2A C2 H2B 107.3 . . ? N1 C3 C4 112.7(2) . . ? N1 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? N1 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? O3 C4 O2 124.7(3) . . ? O3 C4 C3 118.6(2) . . ? O2 C4 C3 116.7(2) . . ? O4 C5 O5 126.2(3) . . ? O4 C5 C5 117.5(3) . 2_675 ? O5 C5 C5 116.3(3) . 2_675 ? O7 C6 O6 127.2(3) . . ? O7 C6 C6 116.8(3) . 2_665 ? O6 C6 C6 116.0(3) . 2_665 ? C1 N1 C2 123.7(3) . . ? C1 N1 C3 121.2(3) . . ? C2 N1 C3 115.1(2) . . ? Ho1 O1W H1WA 114.6 . . ? Ho1 O1W H1WB 108.9 . . ? H1WA O1W H1WB 113.6 . . ? 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 O1W H1WB O5 0.85 2.05 2.792(3) 145.5 1_455 O1W H1WB O4 0.85 2.64 3.197(3) 124.0 1_455 O1W H1WA O6 0.84 2.32 3.122(3) 157.9 1_455 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.134 _refine_diff_density_min -1.424 _refine_diff_density_rms 0.151 # Attachment 'complex_32.cif' data_complex_3 _database_code_depnum_ccdc_archive 'CCDC 708192' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Er2 N2 O16' _chemical_formula_weight 774.76 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' Er Er -0.2586 4.9576 '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 6.6574(15) _cell_length_b 7.7517(18) _cell_length_c 9.066(2) _cell_angle_alpha 95.676(4) _cell_angle_beta 110.170(3) _cell_angle_gamma 93.544(4) _cell_volume 434.73(17) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3441 _cell_measurement_theta_min 2.413 _cell_measurement_theta_max 28.342 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 9.685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3442 _exptl_absorpt_correction_T_max 0.6980 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex 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 3318 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1656 _reflns_number_gt 1640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXTL-Plus (Sheldrick, 1990)' _computing_cell_refinement 'SHELXTL-Plus (Sheldrick, 1990)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V.5.0 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0320P)^2^+0.0675P] 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 1656 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0189 _refine_ls_R_factor_gt 0.0186 _refine_ls_wR_factor_ref 0.0504 _refine_ls_wR_factor_gt 0.0501 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _refine_ls_shift/su_max 0.008 _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 Er1 Er 0.382174(14) 0.768420(12) 0.216781(11) 0.01426(3) Uani 1 1 d . . . O1 O 0.7185(3) 0.4253(3) 0.6389(3) 0.0371(5) Uani 1 1 d . . . O2 O 0.7479(3) 1.0383(3) 0.6453(2) 0.0271(5) Uani 1 1 d . . . O3 O 0.6720(3) 0.8474(3) 0.4343(2) 0.0316(5) Uani 1 1 d . . . O4 O 0.7199(3) 1.0064(3) -0.0600(2) 0.0262(5) Uani 1 1 d . . . O5 O 0.6619(3) 0.8742(3) 0.1296(2) 0.0267(5) Uani 1 1 d . . . O6 O 0.7061(3) 0.3672(3) 0.0463(2) 0.0278(5) Uani 1 1 d . . . O7 O 0.5820(3) 0.5307(3) 0.2045(2) 0.0249(5) Uani 1 1 d . . . C1 C 0.8495(4) 0.4659(4) 0.5760(3) 0.0249(6) Uani 1 1 d . . . C2 C 1.0934(5) 0.6758(4) 0.5222(4) 0.0300(7) Uani 1 1 d . . . H2A H 1.2241 0.7267 0.6071 0.036 Uiso 1 1 calc R . . H2B H 1.0392 0.7662 0.4565 0.036 Uiso 1 1 calc R . . C3 C 0.8793(5) 0.7669(3) 0.6819(4) 0.0260(7) Uani 1 1 d . . . H3A H 1.0093 0.8290 0.7601 0.031 Uiso 1 1 calc R . . H3B H 0.7928 0.7189 0.7379 0.031 Uiso 1 1 calc R . . C4 C 0.7557(4) 0.8930(3) 0.5777(3) 0.0171(6) Uani 1 1 d . . . C5 C 0.6102(4) 0.9651(4) 0.0198(3) 0.0189(6) Uani 1 1 d . . . C6 C 0.5835(4) 0.4701(3) 0.0734(3) 0.0184(6) Uani 1 1 d . . . N1 N 0.9368(4) 0.6256(3) 0.5918(3) 0.0229(5) Uani 1 1 d . . . O1W O 0.0055(3) 0.7098(3) 0.0939(3) 0.0399(6) Uani 1 1 d . . . H1WA H -0.0459 0.6102 0.1017 0.048 Uiso 1 1 d R . . H1WB H -0.0550 0.7916 0.1254 0.048 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 Er1 0.01682(6) 0.01387(6) 0.01423(6) 0.00136(5) 0.00787(4) 0.00413(5) O1 0.0497(10) 0.0286(10) 0.0586(11) 0.0203(8) 0.0456(8) 0.0156(9) O2 0.0408(10) 0.0199(9) 0.0259(9) -0.0012(8) 0.0180(8) 0.0120(8) O3 0.0280(10) 0.0418(12) 0.0187(9) -0.0036(9) 0.0009(8) 0.0117(9) O4 0.0266(8) 0.0265(9) 0.0370(10) 0.0148(8) 0.0212(7) 0.0114(8) O5 0.0193(8) 0.0341(10) 0.0320(9) 0.0204(8) 0.0105(7) 0.0082(8) O6 0.0256(9) 0.0347(11) 0.0201(9) -0.0051(8) 0.0046(7) 0.0144(8) O7 0.0381(9) 0.0239(9) 0.0171(8) 0.0020(7) 0.0132(7) 0.0150(8) C1 0.0313(11) 0.0239(13) 0.0320(13) 0.0127(10) 0.0223(10) 0.0145(10) C2 0.0391(13) 0.0159(12) 0.0484(15) 0.0061(11) 0.0316(12) 0.0055(11) C3 0.0392(14) 0.0228(14) 0.0205(11) 0.0028(10) 0.0144(10) 0.0127(12) C4 0.0161(10) 0.0176(12) 0.0204(11) 0.0011(9) 0.0097(9) 0.0041(9) C5 0.0173(11) 0.0194(12) 0.0222(12) 0.0050(10) 0.0087(9) 0.0048(10) C6 0.0208(11) 0.0137(12) 0.0208(12) -0.0003(10) 0.0083(10) 0.0000(10) N1 0.0322(10) 0.0200(10) 0.0282(10) 0.0086(8) 0.0220(9) 0.0128(9) O1W 0.0266(10) 0.0403(13) 0.0510(13) -0.0132(11) 0.0178(9) -0.0030(10) _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 Er1 O3 2.2312(19) . ? Er1 O2 2.257(2) 2_676 ? Er1 O1 2.299(2) 2_666 ? Er1 O4 2.345(2) 2_675 ? Er1 O7 2.354(2) . ? Er1 O1W 2.360(2) . ? Er1 O6 2.366(2) 2_665 ? Er1 O5 2.392(2) . ? O1 C1 1.237(4) . ? O1 Er1 2.299(2) 2_666 ? O2 C4 1.241(3) . ? O2 Er1 2.257(2) 2_676 ? O3 C4 1.229(3) . ? O4 C5 1.241(4) . ? O4 Er1 2.345(2) 2_675 ? O5 C5 1.241(3) . ? O6 C6 1.242(3) . ? O6 Er1 2.366(2) 2_665 ? O7 C6 1.237(3) . ? C1 N1 1.308(4) . ? C1 C2 1.495(4) 2_766 ? C2 N1 1.445(4) . ? C2 C1 1.495(4) 2_766 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.450(4) . ? C3 C4 1.507(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C5 1.532(5) 2_675 ? C6 C6 1.546(5) 2_665 ? O1W H1WA 0.8446 . ? O1W H1WB 0.8493 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Er1 O2 79.06(8) . 2_676 ? O3 Er1 O1 85.85(8) . 2_666 ? O2 Er1 O1 83.15(8) 2_676 2_666 ? O3 Er1 O4 113.36(8) . 2_675 ? O2 Er1 O4 74.14(7) 2_676 2_675 ? O1 Er1 O4 146.10(7) 2_666 2_675 ? O3 Er1 O7 79.88(7) . . ? O2 Er1 O7 150.77(7) 2_676 . ? O1 Er1 O7 75.31(8) 2_666 . ? O4 Er1 O7 133.44(7) 2_675 . ? O3 Er1 O1W 150.05(9) . . ? O2 Er1 O1W 76.15(8) 2_676 . ? O1 Er1 O1W 74.82(8) 2_666 . ? O4 Er1 O1W 75.51(8) 2_675 . ? O7 Er1 O1W 115.78(8) . . ? O3 Er1 O6 139.22(8) . 2_665 ? O2 Er1 O6 138.91(7) 2_676 2_665 ? O1 Er1 O6 108.76(8) 2_666 2_665 ? O4 Er1 O6 75.49(7) 2_675 2_665 ? O7 Er1 O6 68.22(7) . 2_665 ? O1W Er1 O6 69.91(8) . 2_665 ? O3 Er1 O5 73.50(8) . . ? O2 Er1 O5 117.87(7) 2_676 . ? O1 Er1 O5 145.90(7) 2_666 . ? O4 Er1 O5 67.99(7) 2_675 . ? O7 Er1 O5 74.56(7) . . ? O1W Er1 O5 133.65(8) . . ? O6 Er1 O5 73.98(7) 2_665 . ? C1 O1 Er1 146.1(2) . 2_666 ? C4 O2 Er1 155.0(2) . 2_676 ? C4 O3 Er1 151.1(2) . . ? C5 O4 Er1 118.36(17) . 2_675 ? C5 O5 Er1 116.89(17) . . ? C6 O6 Er1 117.97(16) . 2_665 ? C6 O7 Er1 118.19(17) . . ? O1 C1 N1 122.7(3) . . ? O1 C1 C2 117.5(3) . 2_766 ? N1 C1 C2 119.8(3) . 2_766 ? N1 C2 C1 116.4(2) . 2_766 ? N1 C2 H2A 108.2 . . ? C1 C2 H2A 108.2 2_766 . ? N1 C2 H2B 108.2 . . ? C1 C2 H2B 108.2 2_766 . ? H2A C2 H2B 107.3 . . ? N1 C3 C4 112.1(2) . . ? N1 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? O3 C4 O2 124.7(3) . . ? O3 C4 C3 119.1(2) . . ? O2 C4 C3 116.3(2) . . ? O5 C5 O4 126.5(2) . . ? O5 C5 C5 116.6(3) . 2_675 ? O4 C5 C5 116.9(3) . 2_675 ? O7 C6 O6 127.2(2) . . ? O7 C6 C6 116.8(3) . 2_665 ? O6 C6 C6 116.0(3) . 2_665 ? C1 N1 C2 123.8(2) . . ? C1 N1 C3 121.1(3) . . ? C2 N1 C3 115.1(2) . . ? Er1 O1W H1WA 115.2 . . ? Er1 O1W H1WB 109.4 . . ? H1WA O1W H1WB 112.7 . . ? 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 O1W H1WB O5 0.85 2.04 2.785(3) 146.1 1_455 O1W H1WB O4 0.85 2.64 3.193(3) 123.9 1_455 O1W H1WA O6 0.84 2.32 3.120(3) 158.3 1_455 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.879 _refine_diff_density_min -1.322 _refine_diff_density_rms 0.142 # Attachment 'complex_42.cif' data_complex_4 _database_code_depnum_ccdc_archive 'CCDC 708193' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 N2 O16 Yb2' _chemical_formula_weight 786.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 6.6649(15) _cell_length_b 7.7808(17) _cell_length_c 9.076(2) _cell_angle_alpha 95.798(3) _cell_angle_beta 109.928(3) _cell_angle_gamma 93.594(3) _cell_volume 437.83(17) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3400 _cell_measurement_theta_min 2.408 _cell_measurement_theta_max 28.220 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.982 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 366 _exptl_absorpt_coefficient_mu 10.713 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3596 _exptl_absorpt_correction_T_max 0.7394 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex 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 3318 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1664 _reflns_number_gt 1659 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXTL-Plus (Sheldrick, 1990)' _computing_cell_refinement 'SHELXTL-Plus (Sheldrick, 1990)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V.5.0 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0321P)^2^+0.8514P] 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 1664 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0206 _refine_ls_wR_factor_ref 0.0539 _refine_ls_wR_factor_gt 0.0538 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.006 _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 0.383087(17) 0.768855(14) 0.216466(13) 0.01387(4) Uani 1 1 d . . . O1 O 0.7161(4) 0.4231(3) 0.6391(3) 0.0358(6) Uani 1 1 d . . . O2 O 0.7460(4) 1.0402(3) 0.6453(3) 0.0254(6) Uani 1 1 d . . . O3 O 0.6698(4) 0.8471(4) 0.4334(3) 0.0310(7) Uani 1 1 d . . . O4 O 0.7202(4) 1.0083(3) -0.0613(3) 0.0247(5) Uani 1 1 d . . . O5 O 0.6629(4) 0.8744(3) 0.1297(3) 0.0263(6) Uani 1 1 d . . . O6 O 0.7047(4) 0.3647(3) 0.0459(3) 0.0268(6) Uani 1 1 d . . . O7 O 0.5829(4) 0.5332(3) 0.2051(3) 0.0240(6) Uani 1 1 d . . . C1 C 0.8470(5) 0.4651(4) 0.5752(4) 0.0243(7) Uani 1 1 d . . . C2 C 1.0909(6) 0.6765(4) 0.5217(5) 0.0295(8) Uani 1 1 d . . . H2A H 1.2200 0.7297 0.6062 0.035 Uiso 1 1 calc R . . H2B H 1.0351 0.7649 0.4550 0.035 Uiso 1 1 calc R . . C3 C 0.8771(6) 0.7675(4) 0.6823(4) 0.0259(8) Uani 1 1 d . . . H3A H 1.0067 0.8295 0.7602 0.031 Uiso 1 1 calc R . . H3B H 0.7904 0.7199 0.7383 0.031 Uiso 1 1 calc R . . C4 C 0.7531(5) 0.8938(4) 0.5772(4) 0.0175(7) Uani 1 1 d . . . C5 C 0.6103(5) 0.9656(4) 0.0199(4) 0.0187(7) Uani 1 1 d . . . C6 C 0.5842(5) 0.4704(4) 0.0738(4) 0.0191(7) Uani 1 1 d . . . N1 N 0.9347(4) 0.6256(4) 0.5913(3) 0.0217(6) Uani 1 1 d . . . O1W O 0.0084(4) 0.7096(4) 0.0947(3) 0.0371(7) Uani 1 1 d . . . H1WA H -0.0468 0.6103 0.1001 0.045 Uiso 1 1 d R . . H1WB H -0.0558 0.7917 0.1238 0.045 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 0.01765(6) 0.01313(7) 0.01359(6) 0.00079(5) 0.00863(5) 0.00528(5) O1 0.0484(11) 0.0241(12) 0.0587(13) 0.0170(11) 0.0439(10) 0.0153(10) O2 0.0362(11) 0.0188(11) 0.0277(11) 0.0003(9) 0.0191(9) 0.0095(10) O3 0.0310(12) 0.0386(14) 0.0186(11) -0.0046(11) 0.0036(10) 0.0115(11) O4 0.0278(10) 0.0260(11) 0.0324(11) 0.0114(9) 0.0224(8) 0.0105(9) O5 0.0204(10) 0.0328(12) 0.0309(11) 0.0192(10) 0.0105(9) 0.0086(10) O6 0.0264(10) 0.0312(12) 0.0208(11) -0.0056(10) 0.0059(9) 0.0157(10) O7 0.0355(11) 0.0227(11) 0.0168(10) 0.0012(9) 0.0118(9) 0.0120(10) C1 0.0302(14) 0.0234(15) 0.0320(15) 0.0138(13) 0.0221(12) 0.0144(13) C2 0.0399(16) 0.0140(14) 0.0487(18) 0.0074(14) 0.0320(14) 0.0073(13) C3 0.0426(17) 0.0207(16) 0.0214(13) 0.0025(12) 0.0182(12) 0.0156(15) C4 0.0167(12) 0.0164(14) 0.0217(13) -0.0003(12) 0.0100(11) 0.0063(11) C5 0.0170(13) 0.0180(14) 0.0208(14) -0.0003(12) 0.0067(11) 0.0041(12) C6 0.0239(14) 0.0150(14) 0.0187(13) -0.0013(12) 0.0089(12) 0.0026(12) N1 0.0321(12) 0.0172(12) 0.0274(12) 0.0069(10) 0.0220(10) 0.0150(11) O1W 0.0248(11) 0.0385(15) 0.0490(15) -0.0098(13) 0.0193(11) -0.0013(11) _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 O3 2.224(2) . ? Yb1 O2 2.246(2) 2_676 ? Yb1 O1 2.292(3) 2_666 ? Yb1 O4 2.333(2) 2_675 ? Yb1 O7 2.347(2) . ? Yb1 O1W 2.354(2) . ? Yb1 O6 2.359(2) 2_665 ? Yb1 O5 2.390(3) . ? Yb1 C5 3.134(4) 2_675 ? Yb1 C6 3.136(3) . ? Yb1 C6 3.147(3) 2_665 ? Yb1 C5 3.150(4) . ? O1 C1 1.245(5) . ? O1 Yb1 2.292(3) 2_666 ? O2 C4 1.251(4) . ? O2 Yb1 2.246(2) 2_676 ? O3 C4 1.236(4) . ? O4 C5 1.257(4) . ? O4 Yb1 2.333(2) 2_675 ? O5 C5 1.247(4) . ? O6 C6 1.251(4) . ? O6 Yb1 2.359(2) 2_665 ? O7 C6 1.245(4) . ? C1 N1 1.317(4) . ? C1 C2 1.506(5) 2_766 ? C2 N1 1.445(5) . ? C2 C1 1.506(5) 2_766 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.461(4) . ? C3 C4 1.521(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C5 1.534(6) 2_675 ? C5 Yb1 3.134(4) 2_675 ? C6 C6 1.560(6) 2_665 ? C6 Yb1 3.147(3) 2_665 ? O1W H1WA 0.8484 . ? O1W H1WB 0.8593 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Yb1 O2 78.75(9) . 2_676 ? O3 Yb1 O1 85.28(10) . 2_666 ? O2 Yb1 O1 82.91(9) 2_676 2_666 ? O3 Yb1 O4 113.78(9) . 2_675 ? O2 Yb1 O4 74.12(9) 2_676 2_675 ? O1 Yb1 O4 145.85(9) 2_666 2_675 ? O3 Yb1 O7 79.64(9) . . ? O2 Yb1 O7 150.23(8) 2_676 . ? O1 Yb1 O7 75.12(9) 2_666 . ? O4 Yb1 O7 133.99(9) 2_675 . ? O3 Yb1 O1W 149.76(10) . . ? O2 Yb1 O1W 76.30(9) 2_676 . ? O1 Yb1 O1W 74.97(10) 2_666 . ? O4 Yb1 O1W 75.25(10) 2_675 . ? O7 Yb1 O1W 115.88(9) . . ? O3 Yb1 O6 139.60(9) . 2_665 ? O2 Yb1 O6 138.84(8) 2_676 2_665 ? O1 Yb1 O6 109.20(10) 2_666 2_665 ? O4 Yb1 O6 75.24(9) 2_675 2_665 ? O7 Yb1 O6 68.84(8) . 2_665 ? O1W Yb1 O6 69.79(9) . 2_665 ? O3 Yb1 O5 73.72(9) . . ? O2 Yb1 O5 117.96(9) 2_676 . ? O1 Yb1 O5 145.66(9) 2_666 . ? O4 Yb1 O5 68.48(8) 2_675 . ? O7 Yb1 O5 74.59(9) . . ? O1W Yb1 O5 133.82(9) . . ? O6 Yb1 O5 74.01(9) 2_665 . ? O3 Yb1 C5 107.04(9) . 2_675 ? O2 Yb1 C5 91.15(9) 2_676 2_675 ? O1 Yb1 C5 165.08(8) 2_666 2_675 ? O4 Yb1 C5 20.63(9) 2_675 2_675 ? O7 Yb1 C5 114.72(9) . 2_675 ? O1W Yb1 C5 90.35(10) . 2_675 ? O6 Yb1 C5 66.95(9) 2_665 2_675 ? O5 Yb1 C5 48.71(8) . 2_675 ? O3 Yb1 C6 95.67(9) . . ? O2 Yb1 C6 170.43(9) 2_676 . ? O1 Yb1 C6 88.92(9) 2_666 . ? O4 Yb1 C6 115.39(9) 2_675 . ? O7 Yb1 C6 20.44(8) . . ? O1W Yb1 C6 106.43(9) . . ? O6 Yb1 C6 49.05(8) 2_665 . ? O5 Yb1 C6 67.06(9) . . ? C5 Yb1 C6 97.96(9) 2_675 . ? O3 Yb1 C6 120.84(9) . 2_665 ? O2 Yb1 C6 159.38(8) 2_676 2_665 ? O1 Yb1 C6 103.77(9) 2_666 2_665 ? O4 Yb1 C6 90.70(9) 2_675 2_665 ? O7 Yb1 C6 48.95(8) . 2_665 ? O1W Yb1 C6 86.51(9) . 2_665 ? O6 Yb1 C6 20.54(8) 2_665 2_665 ? O5 Yb1 C6 66.81(9) . 2_665 ? C5 Yb1 C6 77.47(9) 2_675 2_665 ? C6 Yb1 C6 28.75(11) . 2_665 ? O3 Yb1 C5 89.81(9) . . ? O2 Yb1 C5 110.02(9) 2_676 . ? O1 Yb1 C5 165.03(9) 2_666 . ? O4 Yb1 C5 48.57(8) 2_675 . ? O7 Yb1 C5 90.10(9) . . ? O1W Yb1 C5 114.64(9) . . ? O6 Yb1 C5 66.36(9) 2_665 . ? O5 Yb1 C5 20.77(8) . . ? C5 Yb1 C5 28.25(11) 2_675 . ? C6 Yb1 C5 77.49(9) . . ? C6 Yb1 C5 66.84(9) 2_665 . ? C1 O1 Yb1 146.5(2) . 2_666 ? C4 O2 Yb1 154.6(2) . 2_676 ? C4 O3 Yb1 151.3(2) . . ? C5 O4 Yb1 118.5(2) . 2_675 ? C5 O5 Yb1 116.4(2) . . ? C6 O6 Yb1 118.03(19) . 2_665 ? C6 O7 Yb1 118.4(2) . . ? O1 C1 N1 123.0(3) . . ? O1 C1 C2 117.7(3) . 2_766 ? N1 C1 C2 119.3(3) . 2_766 ? N1 C2 C1 116.7(3) . 2_766 ? N1 C2 H2A 108.1 . . ? C1 C2 H2A 108.1 2_766 . ? N1 C2 H2B 108.1 . . ? C1 C2 H2B 108.1 2_766 . ? H2A C2 H2B 107.3 . . ? N1 C3 C4 111.9(3) . . ? N1 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? O3 C4 O2 125.0(3) . . ? O3 C4 C3 118.9(3) . . ? O2 C4 C3 116.1(3) . . ? O5 C5 O4 126.6(3) . . ? O5 C5 C5 117.1(4) . 2_675 ? O4 C5 C5 116.3(4) . 2_675 ? O5 C5 Yb1 163.7(2) . 2_675 ? O4 C5 Yb1 40.86(16) . 2_675 ? C5 C5 Yb1 76.4(3) 2_675 2_675 ? O5 C5 Yb1 42.82(16) . . ? O4 C5 Yb1 165.5(2) . . ? C5 C5 Yb1 75.3(3) 2_675 . ? Yb1 C5 Yb1 151.75(11) 2_675 . ? O7 C6 O6 127.7(3) . . ? O7 C6 C6 116.4(4) . 2_665 ? O6 C6 C6 115.9(4) . 2_665 ? O7 C6 Yb1 41.18(16) . . ? O6 C6 Yb1 165.9(2) . . ? C6 C6 Yb1 76.0(2) 2_665 . ? O7 C6 Yb1 166.0(2) . 2_665 ? O6 C6 Yb1 41.44(15) . 2_665 ? C6 C6 Yb1 75.2(2) 2_665 2_665 ? Yb1 C6 Yb1 151.25(11) . 2_665 ? C1 N1 C2 123.9(3) . . ? C1 N1 C3 121.3(3) . . ? C2 N1 C3 114.8(3) . . ? Yb1 O1W H1WA 117.0 . . ? Yb1 O1W H1WB 110.8 . . ? H1WA O1W H1WB 111.9 . . ? 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 O1W H1WB O5 0.86 2.04 2.799(4) 147.6 1_455 O1W H1WB O4 0.86 2.66 3.235(4) 125.6 1_455 O1W H1WA O6 0.85 2.34 3.157(4) 160.5 1_455 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.955 _refine_diff_density_min -1.258 _refine_diff_density_rms 0.152