# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Cai-Ming Liu' _publ_contact_author_email CMLIU@ICCAS.AC.CN _publ_section_title ; Carboxylic acid-dependent assembly of neodymium-organic frameworks with attractive topologies and second-order nonlinear optical and/or magnetic properties ; loop_ _publ_author_name 'Cai-Ming Liu' 'De-Qing Zhang' 'Dao-Ben Zhu' 'Jing-Lin Zuo' # Attachment 'complex1-new.CIF' data_4 _database_code_depnum_ccdc_archive 'CCDC 689296' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 N2 Nd O8' _chemical_formula_weight 479.49 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' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 16.670(3) _cell_length_b 9.467(2) _cell_length_c 10.305(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1626.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.958 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 3.239 _exptl_absorpt_correction_type 'psi scan' _exptl_absorpt_correction_T_min 0.7215 _exptl_absorpt_correction_T_max 1.2852 _exptl_absorpt_process_details Abscor _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 'Rigaku R-AXIS RAPID IP Area Detector' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15564 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1527 _reflns_number_gt 1462 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID AUTO (Rigaku, 1998)' _computing_cell_refinement 'RAPID AUTO (Rigaku, 1998)' _computing_data_reduction 'RAPID AUTO (Rigaku, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (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. One ISOR restriant was used for preventing O5 atom from becoming 'non- positive-definite' and one EADP restriant was utillized for restrain the Uij components of C7 and C8 to be approximately equal with an appropriate (usually fairly large) esd. ; _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^)+(0.0404P)^2^+5.1144P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.50(3) _refine_ls_number_reflns 1527 _refine_ls_number_parameters 124 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.157 _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 Nd1 Nd 1.0000 1.44198(3) 0.75721(6) 0.01241(12) Uani 1 2 d S . . C1 C 0.8732(3) 1.1905(6) 0.8853(6) 0.0200(11) Uani 1 1 d . . . C2 C 0.8468(3) 1.2015(6) 1.0090(5) 0.0148(10) Uani 1 1 d . . . H2A H 0.8819 1.2375 1.0708 0.018 Uiso 1 1 calc R . . C3 C 0.7721(4) 1.1632(7) 1.0489(5) 0.0221(12) Uani 1 1 d . . . H3A H 0.7579 1.1756 1.1354 0.026 Uiso 1 1 calc R . . C4 C 0.7178(3) 1.1069(7) 0.9646(6) 0.0205(12) Uani 1 1 d . . . C5 C 0.7422(4) 1.0884(8) 0.8348(6) 0.0263(14) Uani 1 1 d . . . H5A H 0.7070 1.0493 0.7746 0.032 Uiso 1 1 calc R . . C6 C 0.6345(3) 1.0703(6) 1.0073(6) 0.0162(11) Uani 1 1 d . . . C7 C 1.0000 1.9015(14) 0.7968(13) 0.0509(19) Uani 1 2 d S . . H7A H 1.0000 1.9624 0.7223 0.061 Uiso 1 2 d SR . . H7B H 0.9530 1.9194 0.8480 0.061 Uiso 1 1 d R . . C8 C 1.0000 1.7467(10) 0.758(4) 0.0509(19) Uani 1 2 d S . . N1 N 0.8185(4) 1.1282(8) 0.7969(6) 0.0426(16) Uani 1 1 d . . . H1A H 0.8331 1.1149 0.7178 0.051 Uiso 1 1 calc R . . O1 O 0.9419(2) 1.2316(5) 0.8578(5) 0.0268(9) Uani 1 1 d . . . O2 O 0.6173(3) 1.1000(6) 1.1240(4) 0.0270(10) Uani 1 1 d . . . O3 O 0.5886(3) 1.0161(6) 0.9263(5) 0.0297(10) Uani 1 1 d . . . O4 O 1.0558(9) 1.6947(16) 0.6985(15) 0.027(3) Uani 0.50 1 d P . . O5 O 0.9489(10) 1.6736(16) 0.8251(14) 0.024(4) Uani 0.50 1 d PU . . 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 Nd1 0.00826(17) 0.01639(18) 0.01258(17) 0.0003(4) 0.000 0.000 C1 0.018(3) 0.021(3) 0.021(3) 0.002(2) 0.002(2) -0.001(2) C2 0.009(2) 0.020(3) 0.015(2) -0.002(2) 0.0003(18) -0.005(2) C3 0.019(3) 0.035(3) 0.012(2) 0.001(2) 0.001(2) -0.008(2) C4 0.015(3) 0.024(3) 0.022(3) -0.001(2) 0.004(2) -0.003(2) C5 0.017(3) 0.044(4) 0.018(3) -0.006(3) 0.001(2) -0.010(3) C6 0.016(3) 0.022(3) 0.011(2) 0.004(2) -0.003(2) -0.006(2) C7 0.054(4) 0.036(4) 0.063(5) -0.008(5) 0.000 0.000 C8 0.054(4) 0.036(4) 0.063(5) -0.008(5) 0.000 0.000 N1 0.039(3) 0.052(4) 0.037(4) -0.002(3) 0.005(2) -0.006(3) O1 0.019(2) 0.028(2) 0.034(2) 0.007(2) 0.0080(17) -0.0066(17) O2 0.012(2) 0.045(3) 0.024(2) -0.003(2) 0.0047(16) -0.0089(19) O3 0.023(2) 0.037(3) 0.029(2) -0.007(2) -0.0029(19) -0.012(2) O4 0.024(5) 0.015(5) 0.042(6) -0.006(4) 0.023(4) 0.001(4) O5 0.025(4) 0.024(4) 0.025(4) -0.0023(19) 0.0030(19) 0.0000(19) _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 Nd1 O3 2.390(5) 5 ? Nd1 O3 2.390(5) 8_655 ? Nd1 O2 2.422(4) 6_674 ? Nd1 O2 2.422(4) 7_574 ? Nd1 O1 2.446(4) . ? Nd1 O1 2.446(4) 4_755 ? Nd1 O5 2.454(15) 4_755 ? Nd1 O5 2.454(15) . ? Nd1 O4 2.638(15) . ? Nd1 O4 2.638(15) 4_755 ? Nd1 C8 2.885(10) . ? C1 O1 1.243(7) . ? C1 C2 1.353(8) . ? C1 N1 1.417(9) . ? C2 C3 1.359(8) . ? C2 H2A 0.9300 . ? C3 C4 1.363(9) . ? C3 H3A 0.9300 . ? C4 C5 1.410(9) . ? C4 C6 1.497(8) . ? C5 N1 1.382(9) . ? C5 H5A 0.9300 . ? C6 O3 1.243(8) . ? C6 O2 1.268(8) . ? C7 C8 1.519(17) . ? C7 H7A 0.9600 . ? C7 H7B 0.9601 . ? C8 O4 1.22(2) 4_755 ? C8 O4 1.22(2) . ? C8 O5 1.30(3) . ? C8 O5 1.30(3) 4_755 ? N1 H1A 0.8600 . ? O2 Nd1 2.422(4) 6_675 ? O3 Nd1 2.390(5) 5_445 ? O4 O5 1.322(11) 4_755 ? O5 O4 1.322(11) 4_755 ? O5 O5 1.70(3) 4_755 ? 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 Nd1 O3 76.4(2) 5 8_655 ? O3 Nd1 O2 163.86(17) 5 6_674 ? O3 Nd1 O2 87.84(16) 8_655 6_674 ? O3 Nd1 O2 87.84(16) 5 7_574 ? O3 Nd1 O2 163.86(17) 8_655 7_574 ? O2 Nd1 O2 107.7(2) 6_674 7_574 ? O3 Nd1 O1 100.06(17) 5 . ? O3 Nd1 O1 71.66(18) 8_655 . ? O2 Nd1 O1 77.71(16) 6_674 . ? O2 Nd1 O1 115.23(17) 7_574 . ? O3 Nd1 O1 71.66(18) 5 4_755 ? O3 Nd1 O1 100.06(17) 8_655 4_755 ? O2 Nd1 O1 115.23(17) 6_674 4_755 ? O2 Nd1 O1 77.71(16) 7_574 4_755 ? O1 Nd1 O1 46.6(2) . 4_755 ? O3 Nd1 O5 46.8(4) 5 4_755 ? O3 Nd1 O5 75.2(4) 8_655 4_755 ? O2 Nd1 O5 126.1(4) 6_674 4_755 ? O2 Nd1 O5 91.6(4) 7_574 4_755 ? O1 Nd1 O5 138.1(4) . 4_755 ? O1 Nd1 O5 118.0(4) 4_755 4_755 ? O3 Nd1 O5 75.2(4) 5 . ? O3 Nd1 O5 46.8(4) 8_655 . ? O2 Nd1 O5 91.6(4) 6_674 . ? O2 Nd1 O5 126.1(4) 7_574 . ? O1 Nd1 O5 118.0(4) . . ? O1 Nd1 O5 138.1(4) 4_755 . ? O5 Nd1 O5 40.6(8) 4_755 . ? O3 Nd1 O4 71.5(4) 5 . ? O3 Nd1 O4 96.8(3) 8_655 . ? O2 Nd1 O4 107.7(4) 6_674 . ? O2 Nd1 O4 74.6(3) 7_574 . ? O1 Nd1 O4 167.4(4) . . ? O1 Nd1 O4 134.1(4) 4_755 . ? O5 Nd1 O4 29.8(3) 4_755 . ? O5 Nd1 O4 51.5(2) . . ? O3 Nd1 O4 96.8(3) 5 4_755 ? O3 Nd1 O4 71.5(4) 8_655 4_755 ? O2 Nd1 O4 74.6(3) 6_674 4_755 ? O2 Nd1 O4 107.7(4) 7_574 4_755 ? O1 Nd1 O4 134.1(4) . 4_755 ? O1 Nd1 O4 167.4(4) 4_755 4_755 ? O5 Nd1 O4 51.5(2) 4_755 4_755 ? O5 Nd1 O4 29.8(3) . 4_755 ? O4 Nd1 O4 41.3(7) . 4_755 ? O3 Nd1 C8 72.8(6) 5 . ? O3 Nd1 C8 72.8(6) 8_655 . ? O2 Nd1 C8 99.5(5) 6_674 . ? O2 Nd1 C8 99.5(5) 7_574 . ? O1 Nd1 C8 144.5(6) . . ? O1 Nd1 C8 144.5(6) 4_755 . ? O5 Nd1 C8 26.6(6) 4_755 . ? O5 Nd1 C8 26.6(6) . . ? O4 Nd1 C8 25.0(5) . . ? O4 Nd1 C8 25.0(5) 4_755 . ? O1 C1 C2 119.4(5) . . ? O1 C1 N1 125.3(6) . . ? C2 C1 N1 115.3(5) . . ? C1 C2 C3 124.2(5) . . ? C1 C2 H2A 117.9 . . ? C3 C2 H2A 117.9 . . ? C2 C3 C4 121.3(5) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C3 C4 C5 117.5(5) . . ? C3 C4 C6 121.3(5) . . ? C5 C4 C6 121.2(6) . . ? N1 C5 C4 119.9(6) . . ? N1 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? O3 C6 O2 126.1(6) . . ? O3 C6 C4 118.0(6) . . ? O2 C6 C4 115.9(5) . . ? C8 C7 H7A 111.6 . . ? C8 C7 H7B 108.4 . . ? H7A C7 H7B 109.5 . . ? O4 C8 O4 100(3) 4_755 . ? O4 C8 O5 63.3(6) 4_755 . ? O4 C8 O5 123.6(10) . . ? O4 C8 O5 123.6(10) 4_755 4_755 ? O4 C8 O5 63.3(6) . 4_755 ? O5 C8 O5 82(2) . 4_755 ? O4 C8 C7 121.5(11) 4_755 . ? O4 C8 C7 121.5(11) . . ? O5 C8 C7 111.9(19) . . ? O5 C8 C7 112(2) 4_755 . ? O4 C8 Nd1 66.1(8) 4_755 . ? O4 C8 Nd1 66.1(8) . . ? O5 C8 Nd1 57.8(7) . . ? O5 C8 Nd1 57.8(7) 4_755 . ? C7 C8 Nd1 165(2) . . ? C5 N1 C1 121.6(6) . . ? C5 N1 H1A 119.2 . . ? C1 N1 H1A 119.2 . . ? C1 O1 Nd1 135.7(4) . . ? C6 O2 Nd1 133.2(4) . 6_675 ? C6 O3 Nd1 172.4(5) . 5_445 ? C8 O4 O5 61.3(19) . 4_755 ? C8 O4 Nd1 89.0(10) . . ? O5 O4 Nd1 67.4(11) 4_755 . ? C8 O5 O4 55.3(17) . 4_755 ? C8 O5 O5 49.0(11) . 4_755 ? O4 O5 O5 93.4(13) 4_755 4_755 ? C8 O5 Nd1 95.5(10) . . ? O4 O5 Nd1 82.8(11) 4_755 . ? O5 O5 Nd1 69.7(4) 4_755 . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.861 _refine_diff_density_min -0.977 _refine_diff_density_rms 0.145 # Attachment 'complex 2-new.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 689297' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N2 Nd O8' _chemical_formula_weight 493.51 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' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.390(3) _cell_length_b 10.085(2) _cell_length_c 10.350(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1710.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.916 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 3.082 _exptl_absorpt_correction_type 'empirical(SADABS, Sheldrick 1996)' _exptl_absorpt_correction_T_min 0.870083 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _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 dtetector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '15x15 microns' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13936 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 33.47 _reflns_number_total 3233 _reflns_number_gt 2591 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (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. One DFIX restraint was used to restrain the distance of C8-C9 to be 1.53(1) angstrom. ; _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^)+(0.0256P)^2^+1.4501P] 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 3233 _refine_ls_number_parameters 128 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0586 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.070 _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 Nd1 Nd 0.0000 0.050429(13) 0.7500 0.01667(4) Uani 1 2 d S . . C1 C 0.36335(11) 0.43211(19) 0.50024(17) 0.0216(3) Uani 1 1 d . . . C2 C 0.28032(11) 0.3898(2) 0.54403(17) 0.0231(3) Uani 1 1 d . . . C3 C 0.25514(13) 0.4031(2) 0.67438(18) 0.0302(4) Uani 1 1 d . . . H3A H 0.2896 0.4438 0.7338 0.036 Uiso 1 1 calc R . . C4 C 0.18111(13) 0.3571(3) 0.7137(2) 0.0326(5) Uani 1 1 d . . . H4A H 0.1655 0.3673 0.7995 0.039 Uiso 1 1 calc R . . C5 C 0.12738(12) 0.2936(2) 0.6252(2) 0.0267(4) Uani 1 1 d . . . C6 C 0.22712(11) 0.3324(2) 0.45984(18) 0.0258(4) Uani 1 1 d . . . H6A H 0.2413 0.3249 0.3732 0.031 Uiso 1 1 calc R . . C7 C 0.0000 -0.2406(4) 0.7500 0.0433(9) Uani 1 2 d S . . C8 C -0.0177(4) -0.3834(6) 0.7977(7) 0.0562(16) Uani 0.50 1 d PD . . H8A H 0.0327 -0.4308 0.8070 0.067 Uiso 0.50 1 d PR . . H8B H -0.0492 -0.4279 0.7327 0.067 Uiso 0.50 1 d PR . . C9 C -0.0656(6) -0.3917(7) 0.9309(9) 0.096(3) Uani 0.50 1 d PD . . H9A H -0.0748 -0.4830 0.9528 0.143 Uiso 0.50 1 calc PR . . H9B H -0.1171 -0.3470 0.9228 0.143 Uiso 0.50 1 calc PR . . H9C H -0.0339 -0.3502 0.9976 0.143 Uiso 0.50 1 calc PR . . N1 N 0.15406(10) 0.28633(18) 0.50005(16) 0.0279(3) Uani 1 1 d . . . H1A H 0.1224 0.2503 0.4438 0.033 Uiso 1 1 calc R . . O1 O 0.40926(9) 0.4850(2) 0.58115(15) 0.0352(4) Uani 1 1 d . . . O2 O 0.38160(8) 0.41118(17) 0.38389(14) 0.0300(3) Uani 1 1 d . . . O3 O 0.05851(9) 0.24790(18) 0.65319(16) 0.0354(4) Uani 1 1 d . . . O4 O -0.05308(10) -0.17861(17) 0.68573(17) 0.0368(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd1 0.01037(6) 0.02448(7) 0.01515(6) 0.000 -0.00046(4) 0.000 C1 0.0160(7) 0.0296(9) 0.0191(8) 0.0030(7) 0.0001(6) -0.0051(6) C2 0.0172(7) 0.0338(9) 0.0181(7) -0.0007(7) 0.0026(6) -0.0065(7) C3 0.0237(9) 0.0467(12) 0.0201(8) -0.0040(9) 0.0009(7) -0.0100(9) C4 0.0272(10) 0.0497(13) 0.0210(8) -0.0007(9) 0.0073(7) -0.0068(9) C5 0.0204(8) 0.0314(9) 0.0284(9) 0.0035(8) 0.0048(7) -0.0031(7) C6 0.0191(8) 0.0390(11) 0.0193(7) -0.0034(8) 0.0036(6) -0.0078(8) C7 0.046(2) 0.0267(14) 0.057(2) 0.000 -0.0198(16) 0.000 C8 0.072(4) 0.030(2) 0.067(4) 0.001(2) -0.015(4) -0.008(3) C9 0.097(6) 0.044(4) 0.147(9) 0.010(5) -0.027(6) -0.032(4) N1 0.0183(7) 0.0397(10) 0.0257(8) -0.0043(7) 0.0007(6) -0.0114(6) O1 0.0228(7) 0.0550(10) 0.0279(7) -0.0038(7) -0.0049(6) -0.0150(7) O2 0.0205(6) 0.0471(9) 0.0224(6) -0.0021(6) 0.0060(5) -0.0086(6) O3 0.0212(7) 0.0412(9) 0.0437(9) 0.0079(7) 0.0092(6) -0.0077(6) O4 0.0350(8) 0.0354(8) 0.0400(9) -0.0032(7) -0.0188(7) -0.0022(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 Nd1 O1 2.3878(15) 8_655 ? Nd1 O1 2.3878(15) 6_557 ? Nd1 O2 2.4159(14) 2 ? Nd1 O2 2.4159(14) 4_456 ? Nd1 O3 2.4269(16) . ? Nd1 O3 2.4269(16) 3_556 ? Nd1 O4 2.5563(17) . ? Nd1 O4 2.5563(17) 3_556 ? Nd1 C7 2.935(4) . ? C1 O1 1.246(2) . ? C1 O2 1.259(2) . ? C1 C2 1.496(2) . ? C2 C6 1.362(2) . ? C2 C3 1.417(3) . ? C3 C4 1.361(3) . ? C3 H3A 0.9300 . ? C4 C5 1.422(3) . ? C4 H4A 0.9300 . ? C5 O3 1.253(2) . ? C5 N1 1.369(3) . ? C6 N1 1.350(2) . ? C6 H6A 0.9300 . ? C7 O4 1.261(2) 3_556 ? C7 O4 1.261(2) . ? C7 C8 1.550(7) 3_556 ? C7 C8 1.550(7) . ? C8 C8 1.145(14) 3_556 ? C8 C9 1.589(8) . ? C8 H8A 0.9600 . ? C8 H8B 0.9599 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? N1 H1A 0.8600 . ? O1 Nd1 2.3878(15) 6_667 ? O2 Nd1 2.4159(14) 2_554 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Nd1 O1 147.90(10) 8_655 6_557 ? O1 Nd1 O2 87.92(5) 8_655 2 ? O1 Nd1 O2 97.17(5) 6_557 2 ? O1 Nd1 O2 97.17(5) 8_655 4_456 ? O1 Nd1 O2 87.92(5) 6_557 4_456 ? O2 Nd1 O2 161.56(8) 2 4_456 ? O1 Nd1 O3 71.25(6) 8_655 . ? O1 Nd1 O3 140.82(6) 6_557 . ? O2 Nd1 O3 77.75(5) 2 . ? O2 Nd1 O3 87.08(6) 4_456 . ? O1 Nd1 O3 140.82(6) 8_655 3_556 ? O1 Nd1 O3 71.25(6) 6_557 3_556 ? O2 Nd1 O3 87.08(6) 2 3_556 ? O2 Nd1 O3 77.75(5) 4_456 3_556 ? O3 Nd1 O3 69.71(8) . 3_556 ? O1 Nd1 O4 76.81(6) 8_655 . ? O1 Nd1 O4 74.26(6) 6_557 . ? O2 Nd1 O4 124.57(5) 2 . ? O2 Nd1 O4 73.87(5) 4_456 . ? O3 Nd1 O4 140.22(6) . . ? O3 Nd1 O4 135.60(6) 3_556 . ? O1 Nd1 O4 74.26(6) 8_655 3_556 ? O1 Nd1 O4 76.81(6) 6_557 3_556 ? O2 Nd1 O4 73.87(5) 2 3_556 ? O2 Nd1 O4 124.57(5) 4_456 3_556 ? O3 Nd1 O4 135.60(6) . 3_556 ? O3 Nd1 O4 140.22(6) 3_556 3_556 ? O4 Nd1 O4 50.74(7) . 3_556 ? O1 Nd1 C7 73.95(5) 8_655 . ? O1 Nd1 C7 73.95(5) 6_557 . ? O2 Nd1 C7 99.22(4) 2 . ? O2 Nd1 C7 99.22(4) 4_456 . ? O3 Nd1 C7 145.14(4) . . ? O3 Nd1 C7 145.14(4) 3_556 . ? O4 Nd1 C7 25.37(3) . . ? O4 Nd1 C7 25.37(3) 3_556 . ? O1 C1 O2 124.85(17) . . ? O1 C1 C2 117.89(17) . . ? O2 C1 C2 117.26(16) . . ? C6 C2 C3 117.58(17) . . ? C6 C2 C1 120.64(16) . . ? C3 C2 C1 121.74(16) . . ? C4 C3 C2 120.77(19) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C5 120.87(19) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? O3 C5 N1 119.10(19) . . ? O3 C5 C4 125.07(19) . . ? N1 C5 C4 115.81(17) . . ? N1 C6 C2 121.13(17) . . ? N1 C6 H6A 119.4 . . ? C2 C6 H6A 119.4 . . ? O4 C7 O4 120.6(3) 3_556 . ? O4 C7 C8 120.0(3) 3_556 3_556 ? O4 C7 C8 114.9(3) . 3_556 ? O4 C7 C8 114.9(3) 3_556 . ? O4 C7 C8 120.0(3) . . ? C8 C7 C8 43.4(5) 3_556 . ? O4 C7 Nd1 60.30(16) 3_556 . ? O4 C7 Nd1 60.30(16) . . ? C8 C7 Nd1 158.3(3) 3_556 . ? C8 C7 Nd1 158.3(3) . . ? C8 C8 C7 68.3(3) 3_556 . ? C8 C8 C9 176.9(5) 3_556 . ? C7 C8 C9 114.7(5) . . ? C8 C8 H8A 69.6 3_556 . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 108.2 . . ? C8 C8 H8B 70.6 3_556 . ? C7 C8 H8B 108.2 . . ? C9 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 N1 C5 123.79(17) . . ? C6 N1 H1A 118.1 . . ? C5 N1 H1A 118.1 . . ? C1 O1 Nd1 170.60(16) . 6_667 ? C1 O2 Nd1 135.47(12) . 2_554 ? C5 O3 Nd1 138.87(15) . . ? C7 O4 Nd1 94.33(17) . . ? 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 O1 C1 C2 C6 179.4(2) . . . . ? O2 C1 C2 C6 -0.7(3) . . . . ? O1 C1 C2 C3 -2.9(3) . . . . ? O2 C1 C2 C3 177.0(2) . . . . ? C6 C2 C3 C4 1.5(3) . . . . ? C1 C2 C3 C4 -176.2(2) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 O3 179.7(2) . . . . ? C3 C4 C5 N1 -1.9(3) . . . . ? C3 C2 C6 N1 -2.0(3) . . . . ? C1 C2 C6 N1 175.80(19) . . . . ? O1 Nd1 C7 O4 87.00(10) 8_655 . . 3_556 ? O1 Nd1 C7 O4 -93.00(10) 6_557 . . 3_556 ? O2 Nd1 C7 O4 1.87(10) 2 . . 3_556 ? O2 Nd1 C7 O4 -178.13(10) 4_456 . . 3_556 ? O3 Nd1 C7 O4 83.66(12) . . . 3_556 ? O3 Nd1 C7 O4 -96.34(12) 3_556 . . 3_556 ? O4 Nd1 C7 O4 180.0 . . . 3_556 ? O1 Nd1 C7 O4 -93.00(10) 8_655 . . . ? O1 Nd1 C7 O4 87.00(10) 6_557 . . . ? O2 Nd1 C7 O4 -178.13(10) 2 . . . ? O2 Nd1 C7 O4 1.87(10) 4_456 . . . ? O3 Nd1 C7 O4 -96.34(12) . . . . ? O3 Nd1 C7 O4 83.66(12) 3_556 . . . ? O4 Nd1 C7 O4 180.0 3_556 . . . ? O1 Nd1 C7 C8 -10.0(7) 8_655 . . 3_556 ? O1 Nd1 C7 C8 170.0(7) 6_557 . . 3_556 ? O2 Nd1 C7 C8 -95.1(7) 2 . . 3_556 ? O2 Nd1 C7 C8 84.9(7) 4_456 . . 3_556 ? O3 Nd1 C7 C8 -13.3(7) . . . 3_556 ? O3 Nd1 C7 C8 166.7(7) 3_556 . . 3_556 ? O4 Nd1 C7 C8 83.0(7) . . . 3_556 ? O4 Nd1 C7 C8 -97.0(7) 3_556 . . 3_556 ? O1 Nd1 C7 C8 170.0(7) 8_655 . . . ? O1 Nd1 C7 C8 -10.0(7) 6_557 . . . ? O2 Nd1 C7 C8 84.9(7) 2 . . . ? O2 Nd1 C7 C8 -95.1(7) 4_456 . . . ? O3 Nd1 C7 C8 166.7(7) . . . . ? O3 Nd1 C7 C8 -13.3(7) 3_556 . . . ? O4 Nd1 C7 C8 -97.0(7) . . . . ? O4 Nd1 C7 C8 83.0(7) 3_556 . . . ? O4 C7 C8 C8 -108.1(7) 3_556 . . 3_556 ? O4 C7 C8 C8 95.6(7) . . . 3_556 ? Nd1 C7 C8 C8 180.000(2) . . . 3_556 ? O4 C7 C8 C9 71.1(6) 3_556 . . . ? O4 C7 C8 C9 -85.2(6) . . . . ? C8 C7 C8 C9 179.2(12) 3_556 . . . ? Nd1 C7 C8 C9 -0.8(12) . . . . ? C2 C6 N1 C5 0.4(3) . . . . ? O3 C5 N1 C6 -180.0(2) . . . . ? C4 C5 N1 C6 1.5(3) . . . . ? O2 C1 O1 Nd1 -105.0(8) . . . 6_667 ? C2 C1 O1 Nd1 74.8(9) . . . 6_667 ? O1 C1 O2 Nd1 0.4(3) . . . 2_554 ? C2 C1 O2 Nd1 -179.47(14) . . . 2_554 ? N1 C5 O3 Nd1 100.7(2) . . . . ? C4 C5 O3 Nd1 -81.0(3) . . . . ? O1 Nd1 O3 C5 -51.7(2) 8_655 . . . ? O1 Nd1 O3 C5 126.6(2) 6_557 . . . ? O2 Nd1 O3 C5 40.3(2) 2 . . . ? O2 Nd1 O3 C5 -150.3(2) 4_456 . . . ? O3 Nd1 O3 C5 131.7(3) 3_556 . . . ? O4 Nd1 O3 C5 -90.0(2) . . . . ? O4 Nd1 O3 C5 -10.8(3) 3_556 . . . ? C7 Nd1 O3 C5 -48.3(3) . . . . ? O4 C7 O4 Nd1 0.0 3_556 . . . ? C8 C7 O4 Nd1 -156.2(3) 3_556 . . . ? C8 C7 O4 Nd1 155.0(3) . . . . ? O1 Nd1 O4 C7 80.31(9) 8_655 . . . ? O1 Nd1 O4 C7 -85.65(10) 6_557 . . . ? O2 Nd1 O4 C7 2.24(12) 2 . . . ? O2 Nd1 O4 C7 -178.08(11) 4_456 . . . ? O3 Nd1 O4 C7 117.41(10) . . . . ? O3 Nd1 O4 C7 -125.73(9) 3_556 . . . ? O4 Nd1 O4 C7 0.0 3_556 . . . ? 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 N1 H1A O4 0.86 1.90 2.760(2) 177.1 5_556 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 33.47 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 1.167 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.101 # Attachment 'complex 3-new.CIF' data_3 _database_code_depnum_ccdc_archive 'CCDC 689298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 N3 Nd O13' _chemical_formula_weight 630.61 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' Nd Nd -0.1943 3.0179 '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 9.180(2) _cell_length_b 10.517(2) _cell_length_c 13.026(3) _cell_angle_alpha 66.45(3) _cell_angle_beta 85.96(3) _cell_angle_gamma 78.70(3) _cell_volume 1130.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 626 _exptl_absorpt_coefficient_mu 2.371 _exptl_absorpt_correction_type 'empirical(SADABS, Sheldrick 1996)' _exptl_absorpt_correction_T_min 0.750497 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _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 dtetector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '15x15 microns' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6924 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4400 _reflns_number_gt 4272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (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^)+(0.0236P)^2^+0.7488P] 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 4400 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0185 _refine_ls_wR_factor_ref 0.0486 _refine_ls_wR_factor_gt 0.0481 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Nd1 Nd -0.222208(11) -0.002763(11) 0.966834(9) 0.01744(5) Uani 1 1 d . . . C1 C -0.0153(2) 0.1487(2) 0.78232(19) 0.0222(4) Uani 1 1 d . . . C2 C 0.0613(2) 0.2288(2) 0.67852(19) 0.0233(5) Uani 1 1 d . . . C3 C -0.0032(3) 0.2754(3) 0.5713(2) 0.0319(5) Uani 1 1 d . . . H3A H -0.0946 0.2537 0.5648 0.038 Uiso 1 1 calc R . . C4 C 0.0659(3) 0.3512(3) 0.4779(2) 0.0381(6) Uani 1 1 d . . . H4A H 0.0228 0.3787 0.4080 0.046 Uiso 1 1 calc R . . C5 C 0.2047(3) 0.3895(3) 0.4857(2) 0.0307(5) Uani 1 1 d . . . C6 C 0.1971(3) 0.2588(3) 0.6845(2) 0.0272(5) Uani 1 1 d . . . H6A H 0.2441 0.2261 0.7536 0.033 Uiso 1 1 calc R . . C7 C 0.0909(2) -0.2348(2) 0.94723(19) 0.0230(5) Uani 1 1 d . . . C8 C 0.1485(3) -0.3695(2) 0.9311(2) 0.0254(5) Uani 1 1 d . . . C9 C 0.2865(3) -0.4537(3) 0.9784(3) 0.0357(6) Uani 1 1 d . . . H9A H 0.3464 -0.4206 1.0131 0.043 Uiso 1 1 calc R . . C10 C 0.3326(3) -0.5818(3) 0.9740(3) 0.0381(6) Uani 1 1 d . . . H10A H 0.4237 -0.6352 1.0057 0.046 Uiso 1 1 calc R . . C11 C 0.2443(3) -0.6357(2) 0.9219(2) 0.0261(5) Uani 1 1 d . . . C12 C 0.0656(3) -0.4206(2) 0.8795(2) 0.0268(5) Uani 1 1 d . . . H12A H -0.0253 -0.3675 0.8473 0.032 Uiso 1 1 calc R . . C13 C -0.4980(2) -0.0579(2) 0.83831(19) 0.0221(4) Uani 1 1 d . . . C14 C -0.5510(3) -0.0941(3) 0.7487(2) 0.0290(5) Uani 1 1 d . . . C15 C -0.4515(3) -0.1408(4) 0.6779(3) 0.0539(9) Uani 1 1 d . . . H15A H -0.3497 -0.1545 0.6888 0.065 Uiso 1 1 calc R . . C16 C -0.5033(4) -0.1660(5) 0.5941(4) 0.0692(12) Uani 1 1 d . . . H16A H -0.4357 -0.1982 0.5492 0.083 Uiso 1 1 calc R . . C17 C -0.6580(3) -0.1447(4) 0.5728(3) 0.0496(8) Uani 1 1 d . . . C18 C -0.6980(3) -0.0798(3) 0.7313(2) 0.0288(5) Uani 1 1 d . . . H18A H -0.7659 -0.0521 0.7782 0.035 Uiso 1 1 calc R . . N1 N 0.2644(2) 0.3357(2) 0.59082(17) 0.0296(4) Uani 1 1 d . . . H1A H 0.3507 0.3517 0.5980 0.036 Uiso 1 1 calc R . . N2 N 0.1141(2) -0.5481(2) 0.87448(18) 0.0276(4) Uani 1 1 d . . . H2A H 0.0598 -0.5759 0.8393 0.033 Uiso 1 1 calc R . . N3 N -0.7488(2) -0.1049(3) 0.6472(2) 0.0363(5) Uani 1 1 d . . . H3B H -0.8432 -0.0954 0.6401 0.044 Uiso 1 1 calc R . . O1W O -0.41245(18) 0.21439(17) 0.86161(14) 0.0290(4) Uani 1 1 d . . . O1 O -0.14494(18) 0.13356(18) 0.77401(14) 0.0297(4) Uani 1 1 d . . . O2 O 0.05208(19) 0.09786(17) 0.87544(13) 0.0274(4) Uani 1 1 d . . . O2W O 0.1484(2) 0.5654(2) 0.20232(17) 0.0462(5) Uani 1 1 d . . . O3 O 0.2733(2) 0.4653(2) 0.40582(16) 0.0432(5) Uani 1 1 d . . . O3W O -1.0654(3) -0.0805(3) 0.6582(2) 0.0583(6) Uani 1 1 d . . . O4 O -0.03956(17) -0.17320(17) 0.91448(15) 0.0274(4) Uani 1 1 d . . . O4W O 0.5643(2) 0.3241(2) 0.62331(17) 0.0413(5) Uani 1 1 d . . . O5 O 0.17790(18) -0.19752(17) 0.99492(15) 0.0282(4) Uani 1 1 d . . . O6 O 0.27866(19) -0.75501(16) 0.91754(14) 0.0280(4) Uani 1 1 d . . . O7 O -0.36120(18) -0.06922(19) 0.84750(15) 0.0301(4) Uani 1 1 d . . . O8 O -0.59414(19) -0.01645(18) 0.89792(14) 0.0294(4) Uani 1 1 d . . . O9 O -0.7148(3) -0.1578(3) 0.4936(2) 0.0665(7) Uani 1 1 d . . . H1WA H -0.4055 0.2418 0.7915 0.080 Uiso 1 1 d R . . H1WB H -0.4988 0.2088 0.8893 0.080 Uiso 1 1 d R . . H2WA H 0.1976 0.5416 0.2626 0.080 Uiso 1 1 d R . . H2WB H 0.1916 0.6297 0.1578 0.080 Uiso 1 1 d R . . H4WA H 0.6023 0.2634 0.5961 0.080 Uiso 1 1 d R . . H4WB H 0.6210 0.3837 0.6030 0.080 Uiso 1 1 d R . . H3WA H -1.1195 -0.0077 0.6107 0.080 Uiso 1 1 d R . . H3WB H -1.0995 -0.0555 0.7117 0.080 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 Nd1 0.01629(7) 0.01785(7) 0.02012(7) -0.00904(5) 0.00022(4) -0.00416(4) C1 0.0223(11) 0.0209(10) 0.0228(11) -0.0087(9) 0.0014(9) -0.0032(8) C2 0.0214(11) 0.0250(11) 0.0232(11) -0.0085(9) 0.0017(9) -0.0063(9) C3 0.0254(12) 0.0403(14) 0.0285(13) -0.0083(11) -0.0022(10) -0.0131(10) C4 0.0330(14) 0.0531(17) 0.0237(12) -0.0050(11) -0.0055(10) -0.0178(12) C5 0.0287(12) 0.0355(13) 0.0237(12) -0.0059(10) 0.0003(10) -0.0088(10) C6 0.0246(12) 0.0334(12) 0.0209(11) -0.0067(9) -0.0014(9) -0.0074(10) C7 0.0221(11) 0.0216(11) 0.0276(12) -0.0112(9) 0.0042(9) -0.0076(9) C8 0.0223(11) 0.0227(11) 0.0340(13) -0.0135(10) 0.0028(9) -0.0060(9) C9 0.0247(12) 0.0349(14) 0.0585(18) -0.0290(13) -0.0048(12) -0.0054(10) C10 0.0250(13) 0.0325(14) 0.0611(19) -0.0238(13) -0.0078(12) -0.0007(10) C11 0.0242(11) 0.0236(11) 0.0323(13) -0.0126(10) 0.0048(10) -0.0066(9) C12 0.0241(11) 0.0232(11) 0.0325(13) -0.0113(10) -0.0022(10) -0.0017(9) C13 0.0229(11) 0.0212(10) 0.0237(11) -0.0096(9) 0.0009(9) -0.0062(9) C14 0.0249(12) 0.0357(13) 0.0334(13) -0.0208(11) 0.0003(10) -0.0055(10) C15 0.0242(14) 0.095(3) 0.068(2) -0.063(2) -0.0020(14) -0.0011(15) C16 0.0332(16) 0.130(4) 0.083(3) -0.088(3) 0.0016(16) -0.0001(19) C17 0.0385(16) 0.076(2) 0.0551(19) -0.0482(18) -0.0042(14) -0.0071(15) C18 0.0239(12) 0.0352(13) 0.0322(13) -0.0184(11) -0.0004(10) -0.0056(10) N1 0.0206(10) 0.0389(12) 0.0285(11) -0.0092(9) -0.0003(8) -0.0124(9) N2 0.0275(10) 0.0264(10) 0.0347(11) -0.0168(9) -0.0024(8) -0.0065(8) N3 0.0232(10) 0.0528(14) 0.0433(13) -0.0288(11) -0.0033(9) -0.0077(10) O1W 0.0223(8) 0.0296(9) 0.0316(9) -0.0094(7) -0.0005(7) -0.0023(7) O1 0.0206(8) 0.0385(10) 0.0270(9) -0.0080(7) 0.0026(7) -0.0102(7) O2 0.0310(9) 0.0276(8) 0.0218(8) -0.0070(7) -0.0032(7) -0.0061(7) O2W 0.0517(12) 0.0467(12) 0.0387(11) -0.0076(9) -0.0126(9) -0.0211(10) O3 0.0379(11) 0.0565(12) 0.0284(10) -0.0032(9) 0.0033(8) -0.0243(9) O3W 0.0406(12) 0.0822(17) 0.0666(16) -0.0466(14) -0.0013(11) -0.0057(12) O4 0.0213(8) 0.0251(8) 0.0394(10) -0.0177(7) -0.0007(7) -0.0010(6) O4W 0.0274(9) 0.0546(12) 0.0443(11) -0.0188(9) 0.0022(8) -0.0155(9) O5 0.0276(9) 0.0238(8) 0.0380(10) -0.0162(7) -0.0034(7) -0.0058(7) O6 0.0311(9) 0.0198(8) 0.0349(9) -0.0132(7) 0.0038(7) -0.0050(7) O7 0.0217(8) 0.0395(10) 0.0368(10) -0.0226(8) -0.0029(7) -0.0051(7) O8 0.0340(9) 0.0332(9) 0.0273(9) -0.0169(7) 0.0065(7) -0.0116(7) O9 0.0472(13) 0.113(2) 0.0706(17) -0.0691(16) -0.0107(12) -0.0094(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Nd1 O8 2.3915(18) 2_457 ? Nd1 O2 2.4204(19) 2_557 ? Nd1 O7 2.4555(18) . ? Nd1 O5 2.4604(16) 2_557 ? Nd1 O4 2.4753(17) . ? Nd1 O1 2.4774(19) . ? Nd1 O6 2.5236(18) 2_547 ? Nd1 O1W 2.533(2) . ? Nd1 O2 2.9142(19) . ? Nd1 C1 3.067(2) . ? C1 O1 1.249(3) . ? C1 O2 1.264(3) . ? C1 C2 1.490(3) . ? C2 C6 1.359(3) . ? C2 C3 1.413(3) . ? C3 C4 1.354(4) . ? C3 H3A 0.9300 . ? C4 C5 1.431(4) . ? C4 H4A 0.9300 . ? C5 O3 1.247(3) . ? C5 N1 1.364(3) . ? C6 N1 1.351(3) . ? C6 H6A 0.9300 . ? C7 O5 1.251(3) . ? C7 O4 1.259(3) . ? C7 C8 1.503(3) . ? C8 C12 1.357(3) . ? C8 C9 1.416(4) . ? C9 C10 1.353(4) . ? C9 H9A 0.9300 . ? C10 C11 1.416(4) . ? C10 H10A 0.9300 . ? C11 O6 1.255(3) . ? C11 N2 1.370(3) . ? C12 N2 1.354(3) . ? C12 H12A 0.9300 . ? C13 O7 1.248(3) . ? C13 O8 1.263(3) . ? C13 C14 1.501(3) . ? C14 C18 1.353(3) . ? C14 C15 1.412(4) . ? C15 C16 1.357(4) . ? C15 H15A 0.9300 . ? C16 C17 1.424(4) . ? C16 H16A 0.9300 . ? C17 O9 1.255(4) . ? C17 N3 1.371(4) . ? C18 N3 1.356(3) . ? C18 H18A 0.9300 . ? N1 H1A 0.8600 . ? N2 H2A 0.8600 . ? N3 H3B 0.8600 . ? O1W H1WA 0.8431 . ? O1W H1WB 0.8504 . ? O2 Nd1 2.4204(19) 2_557 ? O2W H2WA 0.8561 . ? O2W H2WB 0.8430 . ? O3W H3WA 0.8553 . ? O3W H3WB 0.8580 . ? O4W H4WA 0.8553 . ? O4W H4WB 0.8419 . ? O5 Nd1 2.4604(16) 2_557 ? O6 Nd1 2.5236(18) 2_547 ? O8 Nd1 2.3915(18) 2_457 ? 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 O8 Nd1 O2 84.17(6) 2_457 2_557 ? O8 Nd1 O7 101.19(6) 2_457 . ? O2 Nd1 O7 143.20(6) 2_557 . ? O8 Nd1 O5 75.71(6) 2_457 2_557 ? O2 Nd1 O5 72.80(6) 2_557 2_557 ? O7 Nd1 O5 143.95(6) . 2_557 ? O8 Nd1 O4 143.52(6) 2_457 . ? O2 Nd1 O4 79.40(6) 2_557 . ? O7 Nd1 O4 75.00(6) . . ? O5 Nd1 O4 128.31(6) 2_557 . ? O8 Nd1 O1 140.69(6) 2_457 . ? O2 Nd1 O1 122.03(6) 2_557 . ? O7 Nd1 O1 75.72(6) . . ? O5 Nd1 O1 84.46(6) 2_557 . ? O4 Nd1 O1 74.57(7) . . ? O8 Nd1 O6 71.46(6) 2_457 2_547 ? O2 Nd1 O6 75.28(6) 2_557 2_547 ? O7 Nd1 O6 72.23(7) . 2_547 ? O5 Nd1 O6 135.89(6) 2_557 2_547 ? O4 Nd1 O6 72.93(6) . 2_547 ? O1 Nd1 O6 138.97(6) . 2_547 ? O8 Nd1 O1W 74.58(6) 2_457 . ? O2 Nd1 O1W 141.04(6) 2_557 . ? O7 Nd1 O1W 74.05(6) . . ? O5 Nd1 O1W 70.51(6) 2_557 . ? O4 Nd1 O1W 135.11(6) . . ? O1 Nd1 O1W 66.84(6) . . ? O6 Nd1 O1W 125.40(6) 2_547 . ? O8 Nd1 O2 139.20(5) 2_457 . ? O2 Nd1 O2 74.91(6) 2_557 . ? O7 Nd1 O2 116.61(6) . . ? O5 Nd1 O2 64.85(6) 2_557 . ? O4 Nd1 O2 66.27(5) . . ? O1 Nd1 O2 47.27(6) . . ? O6 Nd1 O2 132.83(6) 2_547 . ? O1W Nd1 O2 100.51(6) . . ? O8 Nd1 C1 146.51(6) 2_457 . ? O2 Nd1 C1 99.07(6) 2_557 . ? O7 Nd1 C1 95.87(6) . . ? O5 Nd1 C1 73.57(6) 2_557 . ? O4 Nd1 C1 68.87(6) . . ? O1 Nd1 C1 23.05(6) . . ? O6 Nd1 C1 141.76(6) 2_547 . ? O1W Nd1 C1 82.85(6) . . ? O2 Nd1 C1 24.22(6) . . ? O1 C1 O2 122.0(2) . . ? O1 C1 C2 118.4(2) . . ? O2 C1 C2 119.6(2) . . ? O1 C1 Nd1 50.92(11) . . ? O2 C1 Nd1 71.09(12) . . ? C2 C1 Nd1 169.31(16) . . ? C6 C2 C3 117.8(2) . . ? C6 C2 C1 120.5(2) . . ? C3 C2 C1 121.7(2) . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 120.6(2) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? O3 C5 N1 119.0(2) . . ? O3 C5 C4 125.7(2) . . ? N1 C5 C4 115.3(2) . . ? N1 C6 C2 120.6(2) . . ? N1 C6 H6A 119.7 . . ? C2 C6 H6A 119.7 . . ? O5 C7 O4 126.7(2) . . ? O5 C7 C8 115.8(2) . . ? O4 C7 C8 117.5(2) . . ? C12 C8 C9 117.6(2) . . ? C12 C8 C7 121.6(2) . . ? C9 C8 C7 120.5(2) . . ? C10 C9 C8 121.1(2) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C9 C10 C11 121.0(2) . . ? C9 C10 H10A 119.5 . . ? C11 C10 H10A 119.5 . . ? O6 C11 N2 120.3(2) . . ? O6 C11 C10 124.2(2) . . ? N2 C11 C10 115.5(2) . . ? N2 C12 C8 120.7(2) . . ? N2 C12 H12A 119.7 . . ? C8 C12 H12A 119.7 . . ? O7 C13 O8 124.6(2) . . ? O7 C13 C14 117.3(2) . . ? O8 C13 C14 118.2(2) . . ? C18 C14 C15 117.4(2) . . ? C18 C14 C13 120.6(2) . . ? C15 C14 C13 122.0(2) . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? C15 C16 C17 121.9(3) . . ? C15 C16 H16A 119.1 . . ? C17 C16 H16A 119.1 . . ? O9 C17 N3 119.4(3) . . ? O9 C17 C16 125.9(3) . . ? N3 C17 C16 114.7(3) . . ? C14 C18 N3 121.6(2) . . ? C14 C18 H18A 119.2 . . ? N3 C18 H18A 119.2 . . ? C6 N1 C5 124.4(2) . . ? C6 N1 H1A 117.8 . . ? C5 N1 H1A 117.8 . . ? C12 N2 C11 124.1(2) . . ? C12 N2 H2A 118.0 . . ? C11 N2 H2A 118.0 . . ? C18 N3 C17 123.7(2) . . ? C18 N3 H3B 118.2 . . ? C17 N3 H3B 118.2 . . ? Nd1 O1W H1WA 113.2 . . ? Nd1 O1W H1WB 112.2 . . ? H1WA O1W H1WB 117.2 . . ? C1 O1 Nd1 106.03(14) . . ? C1 O2 Nd1 169.41(15) . 2_557 ? C1 O2 Nd1 84.69(13) . . ? Nd1 O2 Nd1 105.09(6) 2_557 . ? H2WA O2W H2WB 100.4 . . ? H3WA O3W H3WB 90.7 . . ? C7 O4 Nd1 132.62(15) . . ? H4WA O4W H4WB 105.1 . . ? C7 O5 Nd1 143.31(15) . 2_557 ? C11 O6 Nd1 135.37(15) . 2_547 ? C13 O7 Nd1 129.65(15) . . ? C13 O8 Nd1 166.17(15) . 2_457 ? 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 N1 H1A O4W 0.86 1.96 2.786(3) 161.7 . N3 H3B O3W 0.86 2.02 2.865(3) 167.8 . O1W H1WA O4W 0.84 2.02 2.854(3) 167.7 1_455 O1W H1WB O6 0.85 2.04 2.866(2) 164.2 1_465 O1W H1WB O8 0.85 2.64 3.075(3) 113.0 . O2W H2WA O3 0.86 1.84 2.679(3) 167.4 . O2W H2WB O5 0.84 2.16 2.893(3) 144.5 1_564 O4W H4WA O9 0.86 2.02 2.859(3) 166.4 2_556 O4W H4WB O3 0.84 1.98 2.795(3) 162.7 2_666 O3W H3WA O9 0.86 2.13 2.980(4) 170.4 2_356 O3W H3WB O1 0.86 2.39 3.129(3) 144.9 1_455 O3W H3WB O4 0.86 2.48 3.094(3) 129.4 1_455 N2 H2A O2W 0.86 1.99 2.738(3) 144.3 2_556 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.599 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.073 # Attachment 'complex 1-new.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 693704' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 N2 Nd O8' _chemical_formula_weight 479.49 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' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.652(3) _cell_length_b 9.474(2) _cell_length_c 10.332(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1630.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.954 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 3.231 _exptl_absorpt_correction_type 'empirical(SADABS, Sheldrick 1996)' _exptl_absorpt_correction_T_min 0.760431 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _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 dtetector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '15x15 microns' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9076 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0145 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1588 _reflns_number_gt 1463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (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^)+(0.0233P)^2^+1.6905P] 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 1588 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0200 _refine_ls_R_factor_gt 0.0185 _refine_ls_wR_factor_ref 0.0487 _refine_ls_wR_factor_gt 0.0479 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 Nd1 Nd 0.0000 0.057976(18) 0.2500 0.01673(8) Uani 1 2 d S . . C1 C 0.37311(13) 0.1912(3) 0.6221(2) 0.0251(5) Uani 1 1 d . . . C2 C 0.31780(15) 0.1290(3) 0.7108(2) 0.0315(6) Uani 1 1 d . . . H2A H 0.3331 0.1154 0.7965 0.038 Uiso 1 1 calc R . . C3 C 0.24322(14) 0.0894(3) 0.6725(2) 0.0289(5) Uani 1 1 d . . . H3A H 0.2082 0.0496 0.7323 0.035 Uiso 1 1 calc R . . C4 C 0.21799(13) 0.1074(3) 0.5433(2) 0.0231(5) Uani 1 1 d . . . C5 C 0.27229(13) 0.1645(3) 0.4578(2) 0.0259(5) Uani 1 1 d . . . H5A H 0.2578 0.1768 0.3716 0.031 Uiso 1 1 calc R . . C6 C 0.13458(13) 0.0703(2) 0.4999(2) 0.0215(5) Uani 1 1 d . . . C7 C 0.0000 -0.2485(5) 0.2500 0.0434(12) Uani 1 2 d S . . C8 C -0.0136(11) -0.4026(8) 0.2951(14) 0.102(7) Uani 0.50 1 d P . . H8A H 0.0058 -0.4664 0.2299 0.153 Uiso 0.50 1 calc PR . . H8B H -0.0699 -0.4183 0.3088 0.153 Uiso 0.50 1 calc PR . . H8C H 0.0150 -0.4186 0.3744 0.153 Uiso 0.50 1 calc PR . . N1 N 0.34643(11) 0.2028(2) 0.49774(18) 0.0267(4) Uani 1 1 d . . . H1A H 0.3789 0.2366 0.4410 0.032 Uiso 1 1 calc R . . O1 O 0.44232(9) 0.23212(19) 0.65031(18) 0.0314(4) Uani 1 1 d . . . O2 O 0.08919(9) 0.0140(2) 0.57996(17) 0.0325(4) Uani 1 1 d . . . O3 O 0.11644(10) 0.0989(2) 0.38441(16) 0.0305(4) Uani 1 1 d . . . O4 O -0.05307(10) -0.18561(19) 0.18729(19) 0.0353(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd1 0.01092(11) 0.02348(12) 0.01580(12) 0.000 -0.00047(5) 0.000 C1 0.0206(11) 0.0268(12) 0.0279(12) -0.0038(10) -0.0052(9) -0.0014(9) C2 0.0292(12) 0.0449(16) 0.0203(11) 0.0026(11) -0.0061(10) -0.0048(11) C3 0.0232(11) 0.0424(14) 0.0210(12) 0.0024(11) 0.0015(9) -0.0059(11) C4 0.0176(10) 0.0301(12) 0.0216(11) 0.0018(9) -0.0003(9) -0.0050(9) C5 0.0202(11) 0.0372(13) 0.0203(11) 0.0031(10) -0.0026(9) -0.0042(10) C6 0.0176(11) 0.0254(12) 0.0215(11) -0.0029(9) 0.0003(9) -0.0026(8) C7 0.032(2) 0.029(2) 0.069(3) 0.000 -0.0183(18) 0.000 C8 0.106(12) 0.031(3) 0.170(18) 0.028(6) -0.068(13) -0.023(5) N1 0.0194(9) 0.0357(12) 0.0250(10) 0.0038(9) 0.0015(8) -0.0092(8) O1 0.0197(8) 0.0346(10) 0.0398(10) -0.0041(8) -0.0081(7) -0.0051(7) O2 0.0222(8) 0.0475(11) 0.0279(9) 0.0034(8) 0.0040(7) -0.0122(8) O3 0.0220(8) 0.0459(10) 0.0237(9) 0.0028(8) -0.0062(7) -0.0082(8) O4 0.0317(9) 0.0325(10) 0.0417(11) -0.0070(8) -0.0149(8) -0.0024(8) _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 Nd1 O2 2.3995(16) 7 ? Nd1 O2 2.3995(16) 5_556 ? Nd1 O3 2.4163(16) 3 ? Nd1 O3 2.4163(16) . ? Nd1 O1 2.4368(17) 2_554 ? Nd1 O1 2.4368(17) 4_456 ? Nd1 O4 2.5547(18) . ? Nd1 O4 2.5547(18) 3 ? Nd1 C7 2.904(5) . ? C1 O1 1.250(3) . ? C1 N1 1.364(3) . ? C1 C2 1.426(4) . ? C2 C3 1.357(3) . ? C2 H2A 0.9300 . ? C3 C4 1.409(3) . ? C3 H3A 0.9300 . ? C4 C5 1.375(3) . ? C4 C6 1.501(3) . ? C5 N1 1.351(3) . ? C5 H5A 0.9300 . ? C6 O2 1.241(3) . ? C6 O3 1.260(3) . ? C7 O4 1.247(3) 3 ? C7 O4 1.247(3) . ? C7 C8 1.549(9) 3 ? C7 C8 1.549(9) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N1 H1A 0.8600 . ? O1 Nd1 2.4368(17) 2 ? O2 Nd1 2.3995(16) 5_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Nd1 O2 146.97(10) 7 5_556 ? O2 Nd1 O3 96.98(6) 7 3 ? O2 Nd1 O3 88.26(6) 5_556 3 ? O2 Nd1 O3 88.26(6) 7 . ? O2 Nd1 O3 96.98(6) 5_556 . ? O3 Nd1 O3 161.55(9) 3 . ? O2 Nd1 O1 71.25(6) 7 2_554 ? O2 Nd1 O1 141.76(6) 5_556 2_554 ? O3 Nd1 O1 86.71(6) 3 2_554 ? O3 Nd1 O1 78.22(6) . 2_554 ? O2 Nd1 O1 141.76(6) 7 4_456 ? O2 Nd1 O1 71.25(6) 5_556 4_456 ? O3 Nd1 O1 78.22(6) 3 4_456 ? O3 Nd1 O1 86.71(6) . 4_456 ? O1 Nd1 O1 70.61(8) 2_554 4_456 ? O2 Nd1 O4 76.80(7) 7 . ? O2 Nd1 O4 73.43(7) 5_556 . ? O3 Nd1 O4 73.83(6) 3 . ? O3 Nd1 O4 124.63(6) . . ? O1 Nd1 O4 140.03(6) 2_554 . ? O1 Nd1 O4 135.08(6) 4_456 . ? O2 Nd1 O4 73.43(7) 7 3 ? O2 Nd1 O4 76.80(7) 5_556 3 ? O3 Nd1 O4 124.63(6) 3 3 ? O3 Nd1 O4 73.83(6) . 3 ? O1 Nd1 O4 135.08(6) 2_554 3 ? O1 Nd1 O4 140.03(6) 4_456 3 ? O4 Nd1 O4 50.80(8) . 3 ? O2 Nd1 C7 73.49(5) 7 . ? O2 Nd1 C7 73.49(5) 5_556 . ? O3 Nd1 C7 99.23(5) 3 . ? O3 Nd1 C7 99.23(5) . . ? O1 Nd1 C7 144.69(4) 2_554 . ? O1 Nd1 C7 144.69(4) 4_456 . ? O4 Nd1 C7 25.40(4) . . ? O4 Nd1 C7 25.40(4) 3 . ? O1 C1 N1 119.6(2) . . ? O1 C1 C2 125.0(2) . . ? N1 C1 C2 115.4(2) . . ? C3 C2 C1 121.2(2) . . ? C3 C2 H2A 119.4 . . ? C1 C2 H2A 119.4 . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 117.4(2) . . ? C5 C4 C6 120.6(2) . . ? C3 C4 C6 122.0(2) . . ? N1 C5 C4 120.7(2) . . ? N1 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? O2 C6 O3 125.3(2) . . ? O2 C6 C4 117.7(2) . . ? O3 C6 C4 117.0(2) . . ? O4 C7 O4 122.9(4) 3 . ? O4 C7 C8 120.2(7) 3 3 ? O4 C7 C8 113.4(6) . 3 ? O4 C7 C8 113.4(6) 3 . ? O4 C7 C8 120.2(7) . . ? C8 C7 C8 39.1(11) 3 . ? O4 C7 Nd1 61.5(2) 3 . ? O4 C7 Nd1 61.5(2) . . ? C8 C7 Nd1 160.5(5) 3 . ? C8 C7 Nd1 160.5(5) . . ? 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 . . ? C5 N1 C1 124.3(2) . . ? C5 N1 H1A 117.9 . . ? C1 N1 H1A 117.9 . . ? C1 O1 Nd1 135.63(16) . 2 ? C6 O2 Nd1 170.84(17) . 5_556 ? C6 O3 Nd1 134.59(15) . . ? C7 O4 Nd1 93.1(2) . . ? 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 N1 H1A O4 0.86 1.89 2.752(3) 177.7 6_666 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.948 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.079