# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'La-Sheng Long ' _publ_contact_author_email lslong@xmu.edu.cn _publ_author_name 'La-Sheng Long' data_complex1 _database_code_depnum_ccdc_archive 'CCDC 822460' #TrackingRef '- complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Br0.50 Cl N2 Nd1.50 O8 S2' _chemical_formula_weight 743.21 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 16.3890(3) _cell_length_b 12.0113(2) _cell_length_c 12.2966(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2420.63(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5359 _cell_measurement_theta_min 2.9812 _cell_measurement_theta_max 28.9391 _exptl_crystal_description hexagon _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.039 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1430 _exptl_absorpt_coefficient_mu 4.347 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3554 _exptl_absorpt_correction_T_max 0.6704 _exptl_absorpt_process_details 'CrysAlis RED' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _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 6424 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4411 _reflns_number_gt 4114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _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^)+(0.0171P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 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 0.026(11) _refine_ls_number_reflns 4411 _refine_ls_number_parameters 318 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0196 _refine_ls_wR_factor_ref 0.0384 _refine_ls_wR_factor_gt 0.0381 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.004 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 0.5000 0.195880(17) 0.00915(5) Uani 1 2 d S . . Nd2 Nd 0.029847(9) 0.838275(11) 0.281049(12) 0.00982(3) Uani 1 1 d . . . Br1 Br 0.02123(5) 0.79980(6) 0.50922(6) 0.0291(2) Uani 0.50 1 d P . . Cl1 Cl 0.0198(3) 0.7996(3) 0.5076(3) 0.1167(17) Uani 0.50 1 d P . . Cl2 Cl 0.0000 1.0000 0.11748(8) 0.0247(3) Uani 1 2 d S . . S1 S 0.21042(5) 0.47954(6) 0.52027(7) 0.01745(19) Uani 1 1 d . . . O3 O 0.08636(11) 0.64610(14) 0.30198(16) 0.0153(5) Uani 1 1 d . . . O4 O 0.42372(11) 0.77122(15) -0.21078(19) 0.0204(5) Uani 1 1 d . . . C5 C 0.34937(18) 0.4974(2) 0.6418(2) 0.0152(7) Uani 1 1 d . . . O6 O 0.33047(12) 0.40141(15) 0.67836(17) 0.0172(5) Uani 1 1 d . . . O5 O 0.41823(12) 0.53942(15) 0.66110(18) 0.0179(6) Uani 1 1 d . . . O7 O 0.08468(14) 0.47314(15) 0.35943(19) 0.0282(6) Uani 1 1 d . . . C7 C 0.37072(18) 0.8160(3) -0.1514(3) 0.0221(8) Uani 1 1 d . . . O8 O 0.37273(15) 0.91749(16) -0.1266(2) 0.0329(7) Uani 1 1 d . . . C3 C 0.29123(18) 0.5545(2) 0.5700(3) 0.0150(8) Uani 1 1 d . . . C2 C 0.18051(19) 0.5897(2) 0.4409(3) 0.0154(8) Uani 1 1 d . . . C1 C 0.11251(19) 0.5702(2) 0.3650(3) 0.0156(8) Uani 1 1 d . . . C4 C 0.29370(19) 0.6592(3) 0.5280(3) 0.0235(8) Uani 1 1 d . . . H4A H 0.3340 0.7128 0.5465 0.028 Uiso 1 1 calc R . . C8 C 0.30291(19) 0.7492(2) -0.1081(3) 0.0178(8) Uani 1 1 d . . . S2 S 0.23239(5) 0.81495(6) -0.02505(7) 0.0221(2) Uani 1 1 d . . . O9 O 0.05468(12) 0.61472(14) 0.05348(17) 0.0155(5) Uani 1 1 d . . . O10 O 0.09481(13) 0.78040(15) 0.11775(18) 0.0202(6) Uani 1 1 d . . . C12 C 0.10267(18) 0.6966(2) 0.0587(2) 0.0142(7) Uani 1 1 d . . . C10 C 0.2117(2) 0.6083(2) -0.0671(3) 0.0238(9) Uani 1 1 d . . . H10A H 0.1899 0.5350 -0.0690 0.029 Uiso 1 1 calc R . . C9 C 0.17614(18) 0.6945(2) -0.0121(3) 0.0171(8) Uani 1 1 d . . . C6 C 0.22954(19) 0.6794(2) 0.4539(3) 0.0222(8) Uani 1 1 d . . . H6A H 0.2217 0.7482 0.4173 0.027 Uiso 1 1 calc R . . C11 C 0.2841(2) 0.6399(2) -0.1206(3) 0.0239(9) Uani 1 1 d . . . H11A H 0.3166 0.5896 -0.1614 0.029 Uiso 1 1 calc R . . N2 N -0.0192(2) 0.5827(2) -0.2375(3) 0.0553(11) Uani 1 1 d . . . N1 N -0.0643(2) 1.0162(3) -0.2488(2) 0.0536(10) Uani 1 1 d . . . C16 C -0.0137(3) 0.5501(3) -0.3445(3) 0.0508(13) Uani 1 1 d . . . H16A H -0.0275 0.5934 -0.4065 0.061 Uiso 1 1 calc R . . C13 C 0.0000 1.0000 -0.3101(5) 0.0554(18) Uani 1 2 d S . . H13A H 0.0000 1.0000 -0.3874 0.066 Uiso 1 2 calc SR . . C15 C -0.0396(3) 1.0103(4) -0.1427(3) 0.0631(14) Uani 1 1 d . . . H15A H -0.0733 1.0193 -0.0804 0.076 Uiso 1 1 calc R . . C18 C -0.0475(4) 0.6945(4) -0.1952(5) 0.112(2) Uani 1 1 d D . . H18A H -0.0448 0.6950 -0.1148 0.134 Uiso 1 1 calc R . . H18B H -0.0109 0.7537 -0.2228 0.134 Uiso 1 1 calc R . . H18C H -0.0906 0.7039 -0.2070 0.167 Uiso 0.50 1 d PRD . . C20 C -0.1301(6) 0.7168(8) -0.2297(11) 0.087(4) Uani 0.50 1 d P . . H20A H -0.1469 0.7903 -0.2032 0.131 Uiso 0.50 1 calc PR . . H20B H -0.1666 0.6598 -0.1999 0.131 Uiso 0.50 1 calc PR . . H20C H -0.1328 0.7154 -0.3093 0.131 Uiso 0.50 1 calc PR . . C19 C 0.0000 0.5000 -0.1759(4) 0.058(2) Uani 1 2 d S . . H19A H 0.0000 0.5000 -0.0986 0.069 Uiso 1 2 calc SR . . C14 C -0.1492(3) 1.0350(4) -0.2861(5) 0.0931(19) Uani 1 1 d D . . H14A H -0.1566 1.0011 -0.3588 0.112 Uiso 1 1 calc R . . H14B H -0.1875 0.9981 -0.2352 0.112 Uiso 1 1 calc R . . H14C H -0.1605 1.0965 -0.2935 0.140 Uiso 0.50 1 d PRD . . C17 C -0.1680(9) 1.1519(13) -0.2917(11) 0.156(6) Uani 0.50 1 d P . . H17A H -0.2245 1.1616 -0.3159 0.234 Uiso 0.50 1 calc PR . . H17B H -0.1311 1.1882 -0.3434 0.234 Uiso 0.50 1 calc PR . . H17C H -0.1612 1.1855 -0.2196 0.234 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd1 0.00763(9) 0.00976(9) 0.01007(10) 0.000 0.000 -0.00159(9) Nd2 0.00900(6) 0.00896(6) 0.01151(6) -0.00108(7) -0.00066(7) 0.00010(6) Br1 0.0408(5) 0.0304(4) 0.0163(3) 0.0100(3) 0.0081(4) 0.0164(4) Cl1 0.162(4) 0.103(3) 0.085(3) 0.004(2) 0.023(3) -0.007(3) Cl2 0.0461(7) 0.0168(5) 0.0110(5) 0.000 0.000 0.0113(6) S1 0.0172(4) 0.0122(4) 0.0229(4) 0.0032(3) -0.0092(4) -0.0016(3) O3 0.0173(10) 0.0127(9) 0.0161(11) -0.0009(9) -0.0064(10) 0.0037(8) O4 0.0124(10) 0.0252(11) 0.0237(12) 0.0016(11) 0.0099(12) 0.0043(9) C5 0.0153(14) 0.0160(14) 0.0142(14) -0.0063(15) -0.0035(13) 0.0030(14) O6 0.0162(11) 0.0144(10) 0.0212(12) 0.0059(9) -0.0052(10) 0.0000(9) O5 0.0131(11) 0.0167(10) 0.0239(12) 0.0034(9) -0.0115(10) -0.0032(9) O7 0.0351(13) 0.0129(11) 0.0365(14) 0.0040(10) -0.0193(12) -0.0045(10) C7 0.0109(15) 0.0284(18) 0.0271(18) -0.0006(15) 0.0067(15) -0.0005(15) O8 0.0286(13) 0.0146(11) 0.0554(18) -0.0098(11) 0.0150(14) -0.0094(11) C3 0.0103(15) 0.0154(15) 0.0194(17) -0.0023(13) -0.0081(14) -0.0024(13) C2 0.0105(15) 0.0132(15) 0.0226(17) -0.0043(13) -0.0099(15) 0.0046(13) C1 0.0164(16) 0.0154(15) 0.0152(16) -0.0015(13) -0.0065(14) 0.0040(14) C4 0.0212(16) 0.0139(15) 0.0355(18) 0.0016(16) -0.0151(15) -0.0065(15) C8 0.0124(15) 0.0201(16) 0.0208(17) -0.0029(14) 0.0060(16) -0.0026(14) S2 0.0190(4) 0.0130(4) 0.0344(5) -0.0077(4) 0.0160(4) -0.0056(3) O9 0.0166(11) 0.0137(10) 0.0161(11) 0.0035(8) 0.0056(10) -0.0055(9) O10 0.0241(12) 0.0156(10) 0.0208(12) -0.0035(9) 0.0106(11) -0.0005(10) C12 0.0163(16) 0.0159(15) 0.0104(15) 0.0066(12) 0.0007(13) 0.0059(13) C10 0.0264(19) 0.0117(15) 0.033(2) -0.0018(14) 0.0134(17) -0.0032(15) C9 0.0147(15) 0.0170(15) 0.0196(17) 0.0010(13) 0.0030(14) -0.0034(13) C6 0.0216(16) 0.0147(16) 0.0303(18) 0.0042(15) -0.0147(15) 0.0002(15) C11 0.0266(18) 0.0135(16) 0.0314(19) -0.0070(14) 0.0162(16) 0.0021(14) N2 0.078(3) 0.0425(18) 0.045(2) -0.0017(15) -0.002(2) 0.0105(19) N1 0.069(2) 0.067(2) 0.0250(17) -0.0063(16) -0.0096(17) 0.025(2) C16 0.063(3) 0.058(2) 0.031(2) 0.0088(16) -0.001(2) -0.003(3) C13 0.079(4) 0.064(3) 0.022(3) 0.000 0.000 0.031(4) C15 0.064(3) 0.102(3) 0.0227(19) -0.001(3) 0.000(2) 0.033(3) C18 0.179(6) 0.074(3) 0.081(4) -0.003(3) -0.024(5) 0.040(4) C20 0.070(7) 0.082(7) 0.111(10) -0.023(7) 0.010(8) 0.020(6) C19 0.095(5) 0.055(3) 0.022(3) 0.000 0.000 0.015(4) C14 0.097(4) 0.105(4) 0.077(4) -0.030(3) -0.050(4) 0.048(3) C17 0.118(11) 0.272(16) 0.079(9) -0.093(12) 0.008(9) 0.002(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 O9 2.4016(19) 2_565 ? Nd1 O9 2.4016(19) . ? Nd1 O8 2.461(2) 3_545 ? Nd1 O8 2.461(2) 4_465 ? Nd1 O7 2.465(2) . ? Nd1 O7 2.465(2) 2_565 ? Nd1 O3 2.6048(18) . ? Nd1 O3 2.6048(18) 2_565 ? Nd1 C1 2.904(3) . ? Nd1 C1 2.904(3) 2_565 ? Nd2 O4 2.3456(19) 4_465 ? Nd2 O10 2.377(2) . ? Nd2 O5 2.452(2) 4_466 ? Nd2 O6 2.463(2) 3_556 ? Nd2 O3 2.5004(17) . ? Nd2 O5 2.6584(18) 3_556 ? Nd2 Cl1 2.828(4) . ? Nd2 Cl2 2.8387(7) . ? Nd2 Br1 2.8470(7) . ? Nd2 C5 2.911(3) 3_556 ? Nd2 Nd2 4.0063(3) 2_575 ? Cl2 Nd2 2.8387(7) 2_575 ? S1 C3 1.714(3) . ? S1 C2 1.716(3) . ? O3 C1 1.271(3) . ? O4 C7 1.256(4) . ? O4 Nd2 2.3456(19) 4_565 ? C5 O5 1.259(3) . ? C5 O6 1.276(3) . ? C5 C3 1.469(4) . ? C5 Nd2 2.911(3) 3_546 ? O6 Nd2 2.463(2) 3_546 ? O5 Nd2 2.4516(19) 4_566 ? O5 Nd2 2.6584(18) 3_546 ? O7 C1 1.254(3) . ? C7 O8 1.257(4) . ? C7 C8 1.470(4) . ? O8 Nd1 2.461(2) 3 ? C3 C4 1.360(4) . ? C2 C6 1.354(4) . ? C2 C1 1.472(4) . ? C4 C6 1.412(4) . ? C8 C11 1.357(4) . ? C8 S2 1.733(3) . ? S2 C9 1.723(3) . ? O9 C12 1.261(3) . ? O10 C12 1.248(3) . ? C12 C9 1.487(4) . ? C10 C9 1.367(4) . ? C10 C11 1.409(5) . ? N2 C19 1.289(4) . ? N2 C16 1.376(5) . ? N2 C18 1.513(6) . ? N1 C13 1.310(5) . ? N1 C15 1.367(5) . ? N1 C14 1.483(6) . ? C16 C16 1.286(7) 2_565 ? C13 N1 1.310(5) 2_575 ? C15 C15 1.323(9) 2_575 ? C18 C20 1.443(12) . ? C19 N2 1.289(4) 2_565 ? C14 C17 1.440(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Nd1 O9 86.38(9) 2_565 . ? O9 Nd1 O8 80.38(8) 2_565 3_545 ? O9 Nd1 O8 70.28(7) . 3_545 ? O9 Nd1 O8 70.28(7) 2_565 4_465 ? O9 Nd1 O8 80.38(8) . 4_465 ? O8 Nd1 O8 139.50(12) 3_545 4_465 ? O9 Nd1 O7 136.88(6) 2_565 . ? O9 Nd1 O7 117.38(7) . . ? O8 Nd1 O7 75.67(8) 3_545 . ? O8 Nd1 O7 144.32(8) 4_465 . ? O9 Nd1 O7 117.38(7) 2_565 2_565 ? O9 Nd1 O7 136.88(6) . 2_565 ? O8 Nd1 O7 144.32(8) 3_545 2_565 ? O8 Nd1 O7 75.67(8) 4_465 2_565 ? O7 Nd1 O7 70.64(11) . 2_565 ? O9 Nd1 O3 162.64(6) 2_565 . ? O9 Nd1 O3 77.05(6) . . ? O8 Nd1 O3 89.09(7) 3_545 . ? O8 Nd1 O3 111.26(6) 4_465 . ? O7 Nd1 O3 51.21(6) . . ? O7 Nd1 O3 78.99(7) 2_565 . ? O9 Nd1 O3 77.05(6) 2_565 2_565 ? O9 Nd1 O3 162.64(6) . 2_565 ? O8 Nd1 O3 111.26(6) 3_545 2_565 ? O8 Nd1 O3 89.09(7) 4_465 2_565 ? O7 Nd1 O3 78.99(7) . 2_565 ? O7 Nd1 O3 51.21(6) 2_565 2_565 ? O3 Nd1 O3 119.88(9) . 2_565 ? O9 Nd1 C1 157.74(7) 2_565 . ? O9 Nd1 C1 96.81(8) . . ? O8 Nd1 C1 80.02(9) 3_545 . ? O8 Nd1 C1 131.98(8) 4_465 . ? O7 Nd1 C1 25.35(7) . . ? O7 Nd1 C1 74.65(8) 2_565 . ? O3 Nd1 C1 25.95(7) . . ? O3 Nd1 C1 100.48(7) 2_565 . ? O9 Nd1 C1 96.81(8) 2_565 2_565 ? O9 Nd1 C1 157.74(7) . 2_565 ? O8 Nd1 C1 131.98(8) 3_545 2_565 ? O8 Nd1 C1 80.02(9) 4_465 2_565 ? O7 Nd1 C1 74.65(8) . 2_565 ? O7 Nd1 C1 25.35(7) 2_565 2_565 ? O3 Nd1 C1 100.48(7) . 2_565 ? O3 Nd1 C1 25.95(7) 2_565 2_565 ? C1 Nd1 C1 88.55(12) . 2_565 ? O4 Nd2 O10 81.77(8) 4_465 . ? O4 Nd2 O5 83.66(7) 4_465 4_466 ? O10 Nd2 O5 138.99(7) . 4_466 ? O4 Nd2 O6 159.49(6) 4_465 3_556 ? O10 Nd2 O6 81.08(7) . 3_556 ? O5 Nd2 O6 116.76(7) 4_466 3_556 ? O4 Nd2 O3 78.17(6) 4_465 . ? O10 Nd2 O3 69.58(6) . . ? O5 Nd2 O3 143.10(6) 4_466 . ? O6 Nd2 O3 85.36(6) 3_556 . ? O4 Nd2 O5 147.73(6) 4_465 3_556 ? O10 Nd2 O5 110.40(7) . 3_556 ? O5 Nd2 O5 67.46(8) 4_466 3_556 ? O6 Nd2 O5 50.83(6) 3_556 3_556 ? O3 Nd2 O5 133.86(6) . 3_556 ? O4 Nd2 Cl1 103.14(11) 4_465 . ? O10 Nd2 Cl1 144.11(11) . . ? O5 Nd2 Cl1 76.64(11) 4_466 . ? O6 Nd2 Cl1 84.57(11) 3_556 . ? O3 Nd2 Cl1 76.63(9) . . ? O5 Nd2 Cl1 84.51(9) 3_556 . ? O4 Nd2 Cl2 89.71(5) 4_465 . ? O10 Nd2 Cl2 71.26(5) . . ? O5 Nd2 Cl2 70.55(5) 4_466 . ? O6 Nd2 Cl2 95.34(5) 3_556 . ? O3 Nd2 Cl2 140.22(5) . . ? O5 Nd2 Cl2 67.84(5) 3_556 . ? Cl1 Nd2 Cl2 143.12(8) . . ? O4 Nd2 Br1 103.60(6) 4_465 . ? O10 Nd2 Br1 143.84(5) . . ? O5 Nd2 Br1 76.96(5) 4_466 . ? O6 Nd2 Br1 84.05(5) 3_556 . ? O3 Nd2 Br1 76.53(5) . . ? O5 Nd2 Br1 84.24(5) 3_556 . ? Cl1 Nd2 Br1 0.52(11) . . ? Cl2 Nd2 Br1 143.21(2) . . ? O4 Nd2 C5 173.02(7) 4_465 3_556 ? O10 Nd2 C5 99.37(8) . 3_556 ? O5 Nd2 C5 91.10(8) 4_466 3_556 ? O6 Nd2 C5 25.79(7) 3_556 3_556 ? O3 Nd2 C5 108.72(7) . 3_556 ? O5 Nd2 C5 25.61(7) 3_556 3_556 ? Cl1 Nd2 C5 80.01(11) . 3_556 ? Cl2 Nd2 C5 84.18(6) . 3_556 ? Br1 Nd2 C5 79.58(6) . 3_556 ? O4 Nd2 Nd2 111.26(5) 4_465 2_575 ? O10 Nd2 Nd2 113.14(5) . 2_575 ? O5 Nd2 Nd2 40.25(4) 4_466 2_575 ? O6 Nd2 Nd2 85.89(4) 3_556 2_575 ? O3 Nd2 Nd2 170.28(4) . 2_575 ? O5 Nd2 Nd2 36.57(4) 3_556 2_575 ? Cl1 Nd2 Nd2 98.33(8) . 2_575 ? Cl2 Nd2 Nd2 45.117(14) . 2_575 ? Br1 Nd2 Nd2 98.355(14) . 2_575 ? C5 Nd2 Nd2 61.91(6) 3_556 2_575 ? Nd2 Cl2 Nd2 89.77(3) . 2_575 ? C3 S1 C2 91.06(14) . . ? C1 O3 Nd2 148.20(19) . . ? C1 O3 Nd1 90.30(16) . . ? Nd2 O3 Nd1 111.66(7) . . ? C7 O4 Nd2 165.3(2) . 4_565 ? O5 C5 O6 120.9(3) . . ? O5 C5 C3 120.5(3) . . ? O6 C5 C3 118.4(3) . . ? O5 C5 Nd2 65.91(15) . 3_546 ? O6 C5 Nd2 57.08(14) . 3_546 ? C3 C5 Nd2 160.7(2) . 3_546 ? C5 O6 Nd2 97.13(17) . 3_546 ? C5 O5 Nd2 164.53(19) . 4_566 ? C5 O5 Nd2 88.48(17) . 3_546 ? Nd2 O5 Nd2 103.19(7) 4_566 3_546 ? C1 O7 Nd1 97.34(18) . . ? O4 C7 O8 122.6(3) . . ? O4 C7 C8 120.0(3) . . ? O8 C7 C8 117.5(3) . . ? C7 O8 Nd1 109.2(2) . 3 ? C4 C3 C5 129.8(3) . . ? C4 C3 S1 111.9(2) . . ? C5 C3 S1 118.0(2) . . ? C6 C2 C1 130.6(3) . . ? C6 C2 S1 112.1(2) . . ? C1 C2 S1 117.0(2) . . ? O7 C1 O3 120.7(3) . . ? O7 C1 C2 117.3(3) . . ? O3 C1 C2 121.8(3) . . ? O7 C1 Nd1 57.31(16) . . ? O3 C1 Nd1 63.75(15) . . ? C2 C1 Nd1 168.7(2) . . ? C3 C4 C6 112.4(3) . . ? C11 C8 C7 131.2(3) . . ? C11 C8 S2 110.8(2) . . ? C7 C8 S2 118.0(2) . . ? C9 S2 C8 91.64(14) . . ? C12 O9 Nd1 130.01(19) . . ? C12 O10 Nd2 140.69(19) . . ? O10 C12 O9 126.5(3) . . ? O10 C12 C9 116.0(3) . . ? O9 C12 C9 117.5(3) . . ? C9 C10 C11 112.7(3) . . ? C10 C9 C12 130.4(3) . . ? C10 C9 S2 111.3(2) . . ? C12 C9 S2 118.2(2) . . ? C2 C6 C4 112.5(3) . . ? C8 C11 C10 113.5(3) . . ? C19 N2 C16 109.1(3) . . ? C19 N2 C18 123.9(4) . . ? C16 N2 C18 127.0(4) . . ? C13 N1 C15 107.7(4) . . ? C13 N1 C14 126.8(4) . . ? C15 N1 C14 125.4(4) . . ? C16 C16 N2 106.8(2) 2_565 . ? N1 C13 N1 109.7(5) 2_575 . ? C15 C15 N1 107.4(2) 2_575 . ? C20 C18 N2 110.5(6) . . ? N2 C19 N2 108.0(5) 2_565 . ? C17 C14 N1 111.4(7) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.660 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.088 # Attachment '- complex 2.cif' data_complex2 _database_code_depnum_ccdc_archive 'CCDC 822461' #TrackingRef '- complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Br0.25 Cl1.25 Eu1.50 N2 O8 S2' _chemical_formula_weight 743.67 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 16.2850(5) _cell_length_b 11.9314(3) _cell_length_c 12.2099(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2372.42(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2804 _cell_measurement_theta_min 2.6893 _cell_measurement_theta_max 29.0178 _exptl_crystal_description hexagon _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1430 _exptl_absorpt_coefficient_mu 4.725 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4516 _exptl_absorpt_correction_T_max 0.7980 _exptl_absorpt_process_details 'CrysAlis RED' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _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 7680 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.1002 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4506 _reflns_number_gt 4027 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _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^)+(0.0212P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 4506 _refine_ls_number_parameters 318 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Eu1 Eu 0.0000 0.5000 0.19727(6) 0.00895(17) Uani 1 2 d S . . Eu2 Eu 0.02955(3) 0.83940(4) 0.28216(4) 0.00927(12) Uani 1 1 d . . . Br1 Br 0.0301(14) 0.805(2) 0.515(2) 0.020(3) Uani 0.25 1 d P . . Cl1 Cl 0.0127(11) 0.7955(19) 0.5000(16) 0.019(2) Uani 0.75 1 d P . . Cl2 Cl 0.0000 1.0000 0.1197(3) 0.0226(9) Uani 1 2 d S . . S1 S 0.20987(17) 0.4792(2) 0.5209(2) 0.0164(6) Uani 1 1 d . . . O3 O 0.0835(4) 0.6470(5) 0.3020(5) 0.0114(15) Uani 1 1 d . . . O4 O 0.4227(4) 0.7641(6) -0.2153(7) 0.0241(18) Uani 1 1 d . . . C5 C 0.3491(7) 0.4970(9) 0.6417(8) 0.016(2) Uani 1 1 d U . . O6 O 0.3316(5) 0.4005(5) 0.6776(6) 0.0194(19) Uani 1 1 d . . . O5 O 0.4194(4) 0.5381(6) 0.6587(6) 0.0179(18) Uani 1 1 d . . . O7 O 0.0860(5) 0.4716(6) 0.3574(7) 0.029(2) Uani 1 1 d . . . C7 C 0.3724(7) 0.8113(9) -0.1534(9) 0.020(3) Uani 1 1 d U . . O8 O 0.3759(5) 0.9132(6) -0.1282(6) 0.0230(19) Uani 1 1 d U . . C3 C 0.2910(6) 0.5552(9) 0.5716(8) 0.014(2) Uani 1 1 d . . . C2 C 0.1800(7) 0.5903(9) 0.4429(9) 0.019(3) Uani 1 1 d U . . C1 C 0.1118(7) 0.5704(8) 0.3653(9) 0.014(2) Uani 1 1 d . . . C4 C 0.2935(7) 0.6606(10) 0.5285(9) 0.025(3) Uani 1 1 d . . . H4A H 0.3342 0.7146 0.5465 0.030 Uiso 1 1 calc R . . C8 C 0.3021(7) 0.7470(9) -0.1085(10) 0.018(3) Uani 1 1 d . . . S2 S 0.23328(18) 0.8146(2) -0.0236(3) 0.0231(7) Uani 1 1 d . . . O9 O 0.0556(4) 0.6148(5) 0.0589(6) 0.0162(17) Uani 1 1 d . . . O10 O 0.0944(5) 0.7820(6) 0.1187(6) 0.0197(18) Uani 1 1 d . . . C12 C 0.1033(7) 0.6959(8) 0.0635(9) 0.016(2) Uani 1 1 d . . . C10 C 0.2108(7) 0.6061(9) -0.0646(9) 0.017(2) Uani 1 1 d U . . H10A H 0.1884 0.5326 -0.0660 0.021 Uiso 1 1 calc R . . C9 C 0.1762(7) 0.6948(8) -0.0085(10) 0.020(3) Uani 1 1 d . . . C6 C 0.2290(7) 0.6803(8) 0.4543(9) 0.021(3) Uani 1 1 d . . . H6A H 0.2209 0.7491 0.4167 0.026 Uiso 1 1 calc R . . C11 C 0.2835(8) 0.6378(9) -0.1198(11) 0.029(3) Uani 1 1 d . . . H11A H 0.3162 0.5869 -0.1608 0.034 Uiso 1 1 calc R . . N2 N -0.0204(8) 0.5852(9) -0.2351(9) 0.048(3) Uani 1 1 d . . . N1 N -0.0653(8) 1.0181(12) -0.2478(8) 0.053(4) Uani 1 1 d . . . C16 C -0.0122(10) 0.5525(11) -0.3428(10) 0.045(4) Uani 1 1 d . . . H16A H -0.0223 0.5976 -0.4056 0.055 Uiso 1 1 calc R . . C13 C 0.0000 1.0000 -0.3095(16) 0.070(8) Uani 1 2 d S . . H13A H 0.0000 1.0000 -0.3873 0.084 Uiso 1 2 calc SR . . C15 C -0.0416(9) 1.0070(16) -0.1424(9) 0.058(5) Uani 1 1 d . . . H15A H -0.0764 1.0085 -0.0799 0.069 Uiso 1 1 calc R . . C18 C -0.0527(16) 0.6937(14) -0.1917(18) 0.123(10) Uani 1 1 d D . . H18A H -0.0541 0.6900 -0.1107 0.148 Uiso 1 1 calc R . . H18B H -0.0147 0.7547 -0.2126 0.148 Uiso 1 1 calc R . . H18C H -0.0958 0.7031 -0.2035 0.185 Uiso 0.50 1 d PRD . . C20 C -0.134(2) 0.720(3) -0.231(3) 0.092(14) Uani 0.50 1 d P . . H20A H -0.1500 0.7945 -0.2046 0.139 Uiso 0.50 1 calc PR . . H20B H -0.1729 0.6640 -0.2050 0.139 Uiso 0.50 1 calc PR . . H20C H -0.1336 0.7205 -0.3117 0.139 Uiso 0.50 1 calc PR . . C19 C 0.0000 0.5000 -0.1753(14) 0.056(7) Uani 1 2 d S . . H19A H 0.0000 0.5000 -0.0975 0.067 Uiso 1 2 calc SR . . C14 C -0.1492(11) 1.0385(15) -0.2858(15) 0.091(7) Uani 1 1 d D . . H14A H -0.1892 1.0033 -0.2353 0.109 Uiso 1 1 calc R . . H14B H -0.1571 1.0063 -0.3598 0.109 Uiso 1 1 calc R . . H14C H -0.1605 1.1000 -0.2932 0.137 Uiso 0.50 1 d PRD . . C17 C -0.162(3) 1.165(4) -0.289(4) 0.16(3) Uani 0.50 1 d P . . H17A H -0.2172 1.1822 -0.3143 0.244 Uiso 0.50 1 calc PR . . H17B H -0.1214 1.1991 -0.3383 0.244 Uiso 0.50 1 calc PR . . H17C H -0.1541 1.1960 -0.2148 0.244 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.0055(3) 0.0106(3) 0.0108(4) 0.000 0.000 -0.0016(3) Eu2 0.0067(2) 0.0090(2) 0.0122(3) -0.0010(2) -0.0005(2) 0.0001(2) Br1 0.021(8) 0.027(4) 0.013(6) -0.002(4) -0.009(4) 0.002(5) Cl1 0.019(6) 0.029(5) 0.010(5) 0.004(4) -0.004(4) 0.005(4) Cl2 0.041(3) 0.0167(17) 0.0107(17) 0.000 0.000 0.0109(19) S1 0.0120(14) 0.0146(13) 0.0225(15) 0.0017(12) -0.0095(13) -0.0011(12) O3 0.010(4) 0.013(3) 0.011(4) 0.001(4) -0.003(3) 0.002(3) O4 0.017(4) 0.026(4) 0.028(4) 0.008(4) 0.008(4) 0.009(3) C5 0.015(3) 0.017(3) 0.015(3) -0.001(2) -0.001(2) 0.002(2) O6 0.022(5) 0.014(4) 0.022(5) 0.009(4) -0.004(4) 0.006(3) O5 0.006(4) 0.023(4) 0.025(4) 0.004(4) -0.008(3) -0.001(3) O7 0.039(6) 0.011(4) 0.037(5) 0.001(4) -0.020(4) -0.003(4) C7 0.019(3) 0.020(3) 0.022(3) 0.002(2) 0.001(2) -0.001(2) O8 0.023(3) 0.019(2) 0.027(3) -0.0017(19) 0.003(2) -0.0021(19) C3 0.009(6) 0.018(5) 0.014(6) 0.000(5) -0.006(5) -0.003(5) C2 0.018(3) 0.018(3) 0.020(3) 0.000(2) -0.002(2) 0.002(2) C1 0.015(6) 0.012(5) 0.016(6) -0.001(5) 0.003(5) 0.001(5) C4 0.021(7) 0.020(6) 0.034(7) -0.012(7) -0.015(5) -0.003(6) C8 0.012(6) 0.015(5) 0.029(7) 0.002(5) 0.000(6) -0.004(5) S2 0.0206(16) 0.0132(13) 0.0356(18) -0.0085(14) 0.0167(14) -0.0041(13) O9 0.018(4) 0.014(3) 0.016(4) 0.002(3) 0.000(3) -0.008(3) O10 0.016(4) 0.015(4) 0.028(5) -0.005(4) 0.012(4) 0.003(3) C12 0.017(6) 0.017(5) 0.013(6) 0.002(5) 0.001(5) 0.005(5) C10 0.017(3) 0.016(3) 0.019(3) 0.000(2) 0.002(2) -0.001(2) C9 0.020(6) 0.013(5) 0.027(7) 0.002(5) 0.004(5) -0.003(5) C6 0.024(7) 0.007(5) 0.033(7) 0.008(5) -0.009(5) 0.005(5) C11 0.023(7) 0.022(6) 0.040(8) -0.017(6) 0.015(6) 0.001(5) N2 0.058(9) 0.037(6) 0.048(8) -0.002(6) -0.001(7) 0.002(6) N1 0.068(9) 0.065(9) 0.025(6) -0.011(7) -0.015(6) 0.016(8) C16 0.051(11) 0.052(8) 0.033(7) 0.009(7) -0.016(8) -0.001(8) C13 0.12(2) 0.069(15) 0.022(11) 0.000 0.000 0.046(18) C15 0.062(11) 0.100(12) 0.012(6) -0.013(10) -0.006(7) 0.019(12) C18 0.22(3) 0.060(12) 0.093(17) 0.016(13) -0.02(2) 0.044(16) C20 0.08(3) 0.09(3) 0.10(4) 0.01(3) 0.00(3) 0.04(2) C19 0.087(19) 0.068(14) 0.012(9) 0.000 0.000 -0.018(15) C14 0.094(15) 0.116(16) 0.063(11) -0.041(13) -0.048(12) 0.063(13) C17 0.18(5) 0.21(6) 0.10(4) -0.09(5) -0.02(4) 0.10(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O9 2.356(7) 2_565 ? Eu1 O9 2.356(7) . ? Eu1 O8 2.422(8) 3_545 ? Eu1 O8 2.422(8) 4_465 ? Eu1 O7 2.428(8) . ? Eu1 O7 2.428(8) 2_565 ? Eu1 O3 2.562(6) . ? Eu1 O3 2.562(6) 2_565 ? Eu1 C1 2.868(11) . ? Eu1 C1 2.868(11) 2_565 ? Eu1 O4 3.092(7) 4_465 ? Eu1 O4 3.092(7) 3_545 ? Eu2 O4 2.284(7) 4_465 ? Eu2 O10 2.360(7) . ? Eu2 O5 2.424(7) 4_466 ? Eu2 O6 2.426(7) 3_556 ? Eu2 O3 2.470(6) . ? Eu2 O5 2.614(7) 3_556 ? Eu2 Cl1 2.73(2) . ? Eu2 Cl2 2.800(2) . ? Eu2 Br1 2.88(3) . ? Eu2 C5 2.882(11) 3_556 ? Eu2 Eu2 3.9514(9) 2_575 ? Cl2 Eu2 2.800(2) 2_575 ? S1 C2 1.702(11) . ? S1 C3 1.718(10) . ? O3 C1 1.282(11) . ? O4 C7 1.249(12) . ? O4 Eu2 2.284(7) 4_565 ? O4 Eu1 3.092(7) 3 ? C5 O5 1.263(12) . ? C5 O6 1.264(12) . ? C5 C3 1.452(14) . ? C5 Eu2 2.882(11) 3_546 ? O6 Eu2 2.426(7) 3_546 ? O5 Eu2 2.424(7) 4_566 ? O5 Eu2 2.614(7) 3_546 ? O7 C1 1.255(12) . ? C7 O8 1.256(13) . ? C7 C8 1.483(15) . ? C7 Eu1 3.111(11) 3 ? O8 Eu1 2.422(8) 3 ? C3 C4 1.364(15) . ? C2 C6 1.345(14) . ? C2 C1 1.480(15) . ? C4 C6 1.408(14) . ? C8 C11 1.345(14) . ? C8 S2 1.726(12) . ? S2 C9 1.715(10) . ? O9 C12 1.242(12) . ? O10 C12 1.237(12) . ? C12 C9 1.477(15) . ? C10 C9 1.380(14) . ? C10 C11 1.414(15) . ? N2 C19 1.296(13) . ? N2 C16 1.378(14) . ? N2 C18 1.49(2) . ? N1 C13 1.322(15) . ? N1 C15 1.350(14) . ? N1 C14 1.463(18) . ? C16 C16 1.31(2) 2_565 ? C13 N1 1.322(15) 2_575 ? C15 C15 1.37(3) 2_575 ? C18 C20 1.44(4) . ? C19 N2 1.296(13) 2_565 ? C14 C17 1.53(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Eu1 O9 88.4(3) 2_565 . ? O9 Eu1 O8 79.8(3) 2_565 3_545 ? O9 Eu1 O8 71.2(2) . 3_545 ? O9 Eu1 O8 71.2(2) 2_565 4_465 ? O9 Eu1 O8 79.8(3) . 4_465 ? O8 Eu1 O8 139.3(4) 3_545 4_465 ? O9 Eu1 O7 135.9(2) 2_565 . ? O9 Eu1 O7 115.9(3) . . ? O8 Eu1 O7 74.9(3) 3_545 . ? O8 Eu1 O7 145.2(3) 4_465 . ? O9 Eu1 O7 115.9(3) 2_565 2_565 ? O9 Eu1 O7 135.9(2) . 2_565 ? O8 Eu1 O7 145.2(3) 3_545 2_565 ? O8 Eu1 O7 74.9(3) 4_465 2_565 ? O7 Eu1 O7 72.8(4) . 2_565 ? O9 Eu1 O3 163.8(2) 2_565 . ? O9 Eu1 O3 75.9(2) . . ? O8 Eu1 O3 91.4(2) 3_545 . ? O8 Eu1 O3 108.9(2) 4_465 . ? O7 Eu1 O3 52.2(2) . . ? O7 Eu1 O3 78.9(2) 2_565 . ? O9 Eu1 O3 75.9(2) 2_565 2_565 ? O9 Eu1 O3 163.8(2) . 2_565 ? O8 Eu1 O3 108.9(2) 3_545 2_565 ? O8 Eu1 O3 91.4(2) 4_465 2_565 ? O7 Eu1 O3 78.9(2) . 2_565 ? O7 Eu1 O3 52.2(2) 2_565 2_565 ? O3 Eu1 O3 120.1(3) . 2_565 ? O9 Eu1 C1 158.0(3) 2_565 . ? O9 Eu1 C1 95.6(3) . . ? O8 Eu1 C1 81.1(3) 3_545 . ? O8 Eu1 C1 130.8(3) 4_465 . ? O7 Eu1 C1 25.7(3) . . ? O7 Eu1 C1 75.5(3) 2_565 . ? O3 Eu1 C1 26.5(2) . . ? O3 Eu1 C1 100.4(3) 2_565 . ? O9 Eu1 C1 95.6(3) 2_565 2_565 ? O9 Eu1 C1 158.0(3) . 2_565 ? O8 Eu1 C1 130.8(3) 3_545 2_565 ? O8 Eu1 C1 81.1(3) 4_465 2_565 ? O7 Eu1 C1 75.5(3) . 2_565 ? O7 Eu1 C1 25.7(3) 2_565 2_565 ? O3 Eu1 C1 100.4(3) . 2_565 ? O3 Eu1 C1 26.5(2) 2_565 2_565 ? C1 Eu1 C1 88.7(4) . 2_565 ? O9 Eu1 O4 115.1(2) 2_565 4_465 ? O9 Eu1 O4 71.2(2) . 4_465 ? O8 Eu1 O4 138.9(2) 3_545 4_465 ? O8 Eu1 O4 45.2(2) 4_465 4_465 ? O7 Eu1 O4 107.7(2) . 4_465 ? O7 Eu1 O4 65.2(2) 2_565 4_465 ? O3 Eu1 O4 63.71(19) . 4_465 ? O3 Eu1 O4 111.8(2) 2_565 4_465 ? C1 Eu1 O4 86.6(2) . 4_465 ? C1 Eu1 O4 87.6(2) 2_565 4_465 ? O9 Eu1 O4 71.2(2) 2_565 3_545 ? O9 Eu1 O4 115.1(2) . 3_545 ? O8 Eu1 O4 45.2(2) 3_545 3_545 ? O8 Eu1 O4 138.9(2) 4_465 3_545 ? O7 Eu1 O4 65.2(2) . 3_545 ? O7 Eu1 O4 107.7(2) 2_565 3_545 ? O3 Eu1 O4 111.8(2) . 3_545 ? O3 Eu1 O4 63.71(19) 2_565 3_545 ? C1 Eu1 O4 87.6(2) . 3_545 ? C1 Eu1 O4 86.6(2) 2_565 3_545 ? O4 Eu1 O4 171.8(3) 4_465 3_545 ? O4 Eu2 O10 83.2(3) 4_465 . ? O4 Eu2 O5 82.4(3) 4_465 4_466 ? O10 Eu2 O5 139.3(2) . 4_466 ? O4 Eu2 O6 160.9(2) 4_465 3_556 ? O10 Eu2 O6 80.9(3) . 3_556 ? O5 Eu2 O6 116.6(2) 4_466 3_556 ? O4 Eu2 O3 78.7(2) 4_465 . ? O10 Eu2 O3 69.8(2) . . ? O5 Eu2 O3 142.6(2) 4_466 . ? O6 Eu2 O3 85.9(2) 3_556 . ? O4 Eu2 O5 146.2(2) 4_465 3_556 ? O10 Eu2 O5 110.8(2) . 3_556 ? O5 Eu2 O5 66.8(3) 4_466 3_556 ? O6 Eu2 O5 51.3(2) 3_556 3_556 ? O3 Eu2 O5 134.6(2) . 3_556 ? O4 Eu2 Cl1 99.7(4) 4_465 . ? O10 Eu2 Cl1 144.6(5) . . ? O5 Eu2 Cl1 75.5(5) 4_466 . ? O6 Eu2 Cl1 87.4(4) 3_556 . ? O3 Eu2 Cl1 76.2(5) . . ? O5 Eu2 Cl1 86.4(4) 3_556 . ? O4 Eu2 Cl2 89.17(19) 4_465 . ? O10 Eu2 Cl2 71.10(18) . . ? O5 Eu2 Cl2 70.82(17) 4_466 . ? O6 Eu2 Cl2 95.63(17) 3_556 . ? O3 Eu2 Cl2 140.07(16) . . ? O5 Eu2 Cl2 68.27(16) 3_556 . ? Cl1 Eu2 Cl2 143.7(5) . . ? O4 Eu2 Br1 106.1(5) 4_465 . ? O10 Eu2 Br1 142.5(6) . . ? O5 Eu2 Br1 78.1(6) 4_466 . ? O6 Eu2 Br1 80.8(5) 3_556 . ? O3 Eu2 Br1 76.6(6) . . ? O5 Eu2 Br1 81.8(6) 3_556 . ? Cl1 Eu2 Br1 6.6(7) . . ? Cl2 Eu2 Br1 143.2(6) . . ? O4 Eu2 C5 172.0(3) 4_465 3_556 ? O10 Eu2 C5 98.9(3) . 3_556 ? O5 Eu2 C5 91.0(3) 4_466 3_556 ? O6 Eu2 C5 25.8(3) 3_556 3_556 ? O3 Eu2 C5 109.3(3) . 3_556 ? O5 Eu2 C5 26.0(3) 3_556 3_556 ? Cl1 Eu2 C5 83.1(4) . 3_556 ? Cl2 Eu2 C5 84.3(2) . 3_556 ? Br1 Eu2 C5 76.9(5) . 3_556 ? O4 Eu2 Eu2 109.79(18) 4_465 2_575 ? O10 Eu2 Eu2 112.98(17) . 2_575 ? O5 Eu2 Eu2 40.10(16) 4_466 2_575 ? O6 Eu2 Eu2 86.31(16) 3_556 2_575 ? O3 Eu2 Eu2 171.14(15) . 2_575 ? O5 Eu2 Eu2 36.67(15) 3_556 2_575 ? Cl1 Eu2 Eu2 99.3(5) . 2_575 ? Cl2 Eu2 Eu2 45.12(5) . 2_575 ? Br1 Eu2 Eu2 98.1(6) . 2_575 ? C5 Eu2 Eu2 62.2(2) 3_556 2_575 ? O4 Eu2 Eu1 45.96(18) 4_465 . ? O10 Eu2 Eu1 64.12(17) . . ? O5 Eu2 Eu1 124.67(17) 4_466 . ? O6 Eu2 Eu1 116.46(16) 3_556 . ? O3 Eu2 Eu1 33.94(15) . . ? O5 Eu2 Eu1 167.76(16) 3_556 . ? Cl1 Eu2 Eu1 92.5(5) . . ? Cl2 Eu2 Eu1 117.67(5) . . ? Br1 Eu2 Eu1 96.0(6) . . ? C5 Eu2 Eu1 141.8(2) 3_556 . ? Eu2 Eu2 Eu1 154.899(17) 2_575 . ? Eu2 Cl2 Eu2 89.75(10) 2_575 . ? C2 S1 C3 90.6(5) . . ? C1 O3 Eu2 148.1(6) . . ? C1 O3 Eu1 90.2(5) . . ? Eu2 O3 Eu1 113.5(2) . . ? C7 O4 Eu2 163.7(8) . 4_565 ? C7 O4 Eu1 79.2(6) . 3 ? Eu2 O4 Eu1 102.0(2) 4_565 3 ? O5 C5 O6 120.1(10) . . ? O5 C5 C3 120.1(10) . . ? O6 C5 C3 119.6(10) . . ? O5 C5 Eu2 65.1(6) . 3_546 ? O6 C5 Eu2 56.5(5) . 3_546 ? C3 C5 Eu2 161.6(7) . 3_546 ? C5 O6 Eu2 97.7(7) . 3_546 ? C5 O5 Eu2 162.6(7) . 4_566 ? C5 O5 Eu2 88.9(6) . 3_546 ? Eu2 O5 Eu2 103.2(2) 4_566 3_546 ? C1 O7 Eu1 97.1(7) . . ? O4 C7 O8 123.7(11) . . ? O4 C7 C8 119.8(10) . . ? O8 C7 C8 116.4(10) . . ? O4 C7 Eu1 77.5(6) . 3 ? O8 C7 Eu1 46.4(6) . 3 ? C8 C7 Eu1 162.5(8) . 3 ? C7 O8 Eu1 111.5(7) . 3 ? C4 C3 C5 130.5(10) . . ? C4 C3 S1 111.7(8) . . ? C5 C3 S1 117.4(8) . . ? C6 C2 C1 129.7(10) . . ? C6 C2 S1 113.2(9) . . ? C1 C2 S1 116.6(8) . . ? O7 C1 O3 120.2(10) . . ? O7 C1 C2 116.8(10) . . ? O3 C1 C2 122.8(9) . . ? O7 C1 Eu1 57.2(6) . . ? O3 C1 Eu1 63.3(5) . . ? C2 C1 Eu1 169.0(8) . . ? C3 C4 C6 112.3(10) . . ? C11 C8 C7 129.5(12) . . ? C11 C8 S2 111.6(9) . . ? C7 C8 S2 118.8(8) . . ? C9 S2 C8 91.5(5) . . ? C12 O9 Eu1 131.4(7) . . ? C12 O10 Eu2 139.0(7) . . ? O10 C12 O9 126.7(10) . . ? O10 C12 C9 115.2(10) . . ? O9 C12 C9 118.0(9) . . ? C9 C10 C11 111.9(9) . . ? C10 C9 C12 129.1(9) . . ? C10 C9 S2 111.4(8) . . ? C12 C9 S2 119.4(8) . . ? C2 C6 C4 112.1(10) . . ? C8 C11 C10 113.4(11) . . ? C19 N2 C16 106.9(12) . . ? C19 N2 C18 124.7(13) . . ? C16 N2 C18 128.2(13) . . ? C13 N1 C15 107.3(14) . . ? C13 N1 C14 126.7(12) . . ? C15 N1 C14 125.9(14) . . ? C16 C16 N2 107.4(7) 2_565 . ? N1 C13 N1 110.5(17) 2_575 . ? N1 C15 C15 107.2(9) . 2_575 ? C20 C18 N2 113(2) . . ? N2 C19 N2 111.3(16) 2_565 . ? N1 C14 C17 107(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.428 _refine_diff_density_min -0.974 _refine_diff_density_rms 0.193 # Attachment '- complex 3.cif' data_complex3 _database_code_depnum_ccdc_archive 'CCDC 822462' #TrackingRef '- complex 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N2 Nd O8 S2' _chemical_formula_weight 595.68 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' S S 0.1246 0.1234 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7380(4) _cell_length_b 16.5818(4) _cell_length_c 11.5785(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.514(4) _cell_angle_gamma 90.00 _cell_volume 2066.47(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4766 _cell_measurement_theta_min 3.0952 _cell_measurement_theta_max 29.0142 _exptl_crystal_description hexagon _exptl_crystal_colour purple _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.915 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 _exptl_absorpt_coefficient_mu 2.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.58187 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _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 9618 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3630 _reflns_number_gt 3123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3630 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 0.841 _refine_ls_restrained_S_all 0.841 _refine_ls_shift/su_max 0.048 _refine_ls_shift/su_mean 0.009 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 0.30994(2) 0.534071(16) 0.42474(2) 0.00928(14) Uani 1 1 d . . . S2 S -0.01950(13) 0.30060(8) 0.21143(13) 0.0165(3) Uani 1 1 d . . . O1 O 0.5394(3) 0.3621(2) 0.5553(4) 0.0165(8) Uani 1 1 d . . . O5 O 0.1477(4) 0.4457(2) 0.2647(4) 0.0183(9) Uani 1 1 d . . . O6 O 0.1104(3) 0.4916(2) 0.4268(4) 0.0205(9) Uani 1 1 d . . . C4 C 0.3222(5) 0.1686(3) 0.6720(5) 0.0198(13) Uani 1 1 d . . . H4A H 0.2580 0.1390 0.6787 0.024 Uiso 1 1 calc R . . C10 C -0.1226(5) 0.2837(3) 0.3683(5) 0.0198(13) Uani 1 1 d . . . H10A H -0.1677 0.2622 0.4113 0.024 Uiso 1 1 calc R . . C9 C -0.0566(5) 0.3583(3) 0.4003(5) 0.0164(12) Uani 1 1 d . . . H9A H -0.0563 0.3924 0.4642 0.020 Uiso 1 1 calc R . . C8 C 0.0067(5) 0.3734(3) 0.3244(5) 0.0162(12) Uani 1 1 d . . . C7 C 0.0929(5) 0.4420(3) 0.3396(5) 0.0145(12) Uani 1 1 d . . . C11 C -0.1115(5) 0.2474(3) 0.2666(5) 0.0149(12) Uani 1 1 d . . . C5 C 0.4469(5) 0.1465(3) 0.7268(5) 0.0155(12) Uani 1 1 d . . . C3 C 0.3058(5) 0.2411(3) 0.6054(5) 0.0163(12) Uani 1 1 d . . . H3A H 0.2283 0.2645 0.5622 0.020 Uiso 1 1 calc R . . C2 C 0.4131(5) 0.2741(3) 0.6095(5) 0.0139(11) Uani 1 1 d . . . O7 O -0.1865(4) 0.1602(2) 0.0929(4) 0.0219(9) Uani 1 1 d . . . O3 O 0.6219(3) 0.0726(2) 0.8523(3) 0.0148(8) Uani 1 1 d . . . O2 O 0.3442(3) 0.4003(2) 0.5165(4) 0.0197(9) Uani 1 1 d . . . O8 O -0.2124(4) 0.1224(2) 0.2667(4) 0.0215(9) Uani 1 1 d . . . C1 C 0.4348(5) 0.3510(3) 0.5541(5) 0.0135(11) Uani 1 1 d . . . C12 C -0.1742(5) 0.1720(3) 0.2056(5) 0.0162(12) Uani 1 1 d . . . N1 N -0.1905(5) 0.5328(3) 0.1745(5) 0.0306(14) Uani 1 1 d . . . C6 C 0.5057(5) 0.0771(3) 0.8087(5) 0.0131(11) Uani 1 1 d . . . N2 N -0.2684(5) 0.4381(3) 0.0377(4) 0.0219(11) Uani 1 1 d . . . C16 C -0.2635(6) 0.4690(3) 0.1464(6) 0.0239(15) Uani 1 1 d . . . H16A H -0.3047 0.4488 0.1941 0.029 Uiso 1 1 calc R . . C17 C -0.3417(6) 0.3683(4) -0.0293(6) 0.0278(14) Uani 1 1 d . . . H17A H -0.3287 0.3240 0.0293 0.033 Uiso 1 1 calc R . . H17B H -0.3139 0.3512 -0.0938 0.033 Uiso 1 1 calc R . . C14 C -0.1430(7) 0.5438(4) 0.0849(6) 0.0360(17) Uani 1 1 d . . . H14A H -0.0882 0.5838 0.0830 0.043 Uiso 1 1 calc R . . C15 C -0.1933(6) 0.4839(4) -0.0008(6) 0.0294(15) Uani 1 1 d . . . H15A H -0.1790 0.4756 -0.0733 0.035 Uiso 1 1 calc R . . C18 C -0.4796(7) 0.3886(4) -0.0899(7) 0.0396(17) Uani 1 1 d . . . H18A H -0.5254 0.3419 -0.1327 0.059 Uiso 1 1 calc R . . H18B H -0.4929 0.4317 -0.1492 0.059 Uiso 1 1 calc R . . H18C H -0.5075 0.4049 -0.0260 0.059 Uiso 1 1 calc R . . C13 C -0.1610(7) 0.5848(5) 0.2865(7) 0.051(2) Uani 1 1 d . . . H13A H -0.2044 0.5654 0.3359 0.077 Uiso 1 1 calc R . . H13B H -0.1864 0.6391 0.2601 0.077 Uiso 1 1 calc R . . H13C H -0.0732 0.5836 0.3362 0.077 Uiso 1 1 calc R . . S1 S 0.53942(12) 0.21616(8) 0.69644(12) 0.0143(3) Uani 1 1 d . . . O4 O 0.4368(4) 0.0259(2) 0.8321(4) 0.0228(10) 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 0.0102(2) 0.0058(2) 0.0124(2) -0.00012(10) 0.00510(14) -0.00045(10) S2 0.0198(7) 0.0130(7) 0.0212(7) -0.0067(6) 0.0127(6) -0.0073(5) O1 0.019(2) 0.0070(18) 0.023(2) -0.0010(16) 0.0079(16) -0.0047(16) O5 0.022(2) 0.019(2) 0.017(2) -0.0052(17) 0.0113(17) -0.0060(17) O6 0.009(2) 0.019(2) 0.038(2) -0.0113(19) 0.0143(18) -0.0043(16) C4 0.018(3) 0.012(3) 0.027(3) 0.010(2) 0.006(2) -0.006(2) C10 0.017(3) 0.022(3) 0.020(3) -0.007(2) 0.008(2) -0.008(2) C9 0.024(3) 0.013(3) 0.016(3) -0.006(2) 0.012(2) -0.003(2) C8 0.009(3) 0.018(3) 0.018(3) -0.003(2) 0.002(2) -0.004(2) C7 0.004(3) 0.013(3) 0.018(3) -0.002(2) -0.004(2) 0.001(2) C11 0.018(3) 0.010(3) 0.016(3) -0.003(2) 0.006(2) -0.007(2) C5 0.015(3) 0.010(3) 0.022(3) 0.003(2) 0.009(2) -0.001(2) C3 0.017(3) 0.012(3) 0.017(3) 0.002(2) 0.003(2) 0.003(2) C2 0.011(3) 0.014(3) 0.015(3) -0.004(2) 0.003(2) 0.005(2) O7 0.032(2) 0.019(2) 0.019(2) -0.0063(17) 0.0158(18) -0.0104(18) O3 0.020(2) 0.0118(19) 0.0122(18) 0.0062(15) 0.0056(15) 0.0020(15) O2 0.018(2) 0.0111(19) 0.031(2) 0.0056(17) 0.0100(17) -0.0011(17) O8 0.029(2) 0.017(2) 0.018(2) -0.0012(17) 0.0081(17) -0.0078(18) C1 0.015(3) 0.007(3) 0.019(3) -0.003(2) 0.007(2) 0.001(2) C12 0.015(3) 0.013(3) 0.023(3) 0.001(2) 0.010(2) -0.001(2) N1 0.022(3) 0.045(4) 0.022(3) 0.002(2) 0.007(2) 0.007(2) C6 0.023(3) 0.006(3) 0.015(3) 0.007(2) 0.012(2) 0.003(2) N2 0.032(3) 0.021(3) 0.015(2) -0.006(2) 0.013(2) 0.009(2) C16 0.031(4) 0.025(4) 0.019(3) 0.005(2) 0.012(3) 0.011(3) C17 0.041(4) 0.021(3) 0.026(3) 0.000(3) 0.019(3) -0.002(3) C14 0.047(5) 0.043(4) 0.026(4) -0.002(3) 0.023(3) -0.001(3) C15 0.039(4) 0.034(4) 0.019(3) -0.006(3) 0.015(3) 0.000(3) C18 0.039(4) 0.037(4) 0.034(4) 0.012(3) 0.005(3) 0.001(3) C13 0.054(5) 0.071(6) 0.027(4) -0.011(4) 0.014(3) 0.003(4) S1 0.0117(7) 0.0105(7) 0.0203(7) 0.0046(5) 0.0060(5) -0.0008(5) O4 0.036(3) 0.010(2) 0.032(2) 0.0136(17) 0.023(2) 0.0066(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Nd1 O4 2.373(4) 4_565 ? Nd1 O1 2.412(4) 3_666 ? Nd1 O2 2.423(4) . ? Nd1 O6 2.454(4) . ? Nd1 O3 2.462(3) 2_656 ? Nd1 O7 2.505(4) 2 ? Nd1 O8 2.518(4) 2 ? Nd1 O5 2.528(4) . ? Nd1 C7 2.791(5) . ? Nd1 C12 2.850(5) 2 ? Nd1 C6 3.063(5) 2_656 ? S2 C11 1.704(5) . ? S2 C8 1.716(6) . ? O1 C1 1.236(6) . ? O1 Nd1 2.412(4) 3_666 ? O5 C7 1.270(7) . ? O6 C7 1.254(7) . ? C4 C5 1.393(7) . ? C4 C3 1.399(7) . ? C10 C11 1.374(8) . ? C10 C9 1.427(8) . ? C9 C8 1.381(8) . ? C8 C7 1.485(7) . ? C11 C12 1.481(7) . ? C5 C6 1.476(7) . ? C5 S1 1.715(5) . ? C3 C2 1.356(8) . ? C2 C1 1.494(8) . ? C2 S1 1.716(5) . ? O7 C12 1.269(7) . ? O7 Nd1 2.505(4) 2_545 ? O3 C6 1.253(6) . ? O3 Nd1 2.462(3) 2_646 ? O2 C1 1.272(6) . ? O8 C12 1.277(7) . ? O8 Nd1 2.518(4) 2_545 ? C12 Nd1 2.850(5) 2_545 ? N1 C16 1.319(8) . ? N1 C14 1.372(9) . ? N1 C13 1.478(9) . ? C6 O4 1.274(7) . ? C6 Nd1 3.063(5) 2_646 ? N2 C16 1.338(8) . ? N2 C15 1.366(9) . ? N2 C17 1.465(8) . ? C17 C18 1.523(9) . ? C14 C15 1.361(9) . ? O4 Nd1 2.373(4) 4_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Nd1 O1 76.95(13) 4_565 3_666 ? O4 Nd1 O2 77.90(13) 4_565 . ? O1 Nd1 O2 128.63(13) 3_666 . ? O4 Nd1 O6 131.11(13) 4_565 . ? O1 Nd1 O6 150.40(13) 3_666 . ? O2 Nd1 O6 74.06(14) . . ? O4 Nd1 O3 125.63(14) 4_565 2_656 ? O1 Nd1 O3 78.16(13) 3_666 2_656 ? O2 Nd1 O3 81.39(13) . 2_656 ? O6 Nd1 O3 88.66(13) . 2_656 ? O4 Nd1 O7 139.42(13) 4_565 2 ? O1 Nd1 O7 77.89(13) 3_666 2 ? O2 Nd1 O7 142.12(13) . 2 ? O6 Nd1 O7 73.56(14) . 2 ? O3 Nd1 O7 78.73(12) 2_656 2 ? O4 Nd1 O8 89.57(14) 4_565 2 ? O1 Nd1 O8 74.20(13) 3_666 2 ? O2 Nd1 O8 148.87(13) . 2 ? O6 Nd1 O8 94.30(14) . 2 ? O3 Nd1 O8 127.96(12) 2_656 2 ? O7 Nd1 O8 52.98(12) 2 2 ? O4 Nd1 O5 81.43(13) 4_565 . ? O1 Nd1 O5 142.47(13) 3_666 . ? O2 Nd1 O5 74.68(13) . . ? O6 Nd1 O5 53.00(13) . . ? O3 Nd1 O5 138.90(12) 2_656 . ? O7 Nd1 O5 100.45(13) 2 . ? O8 Nd1 O5 75.34(13) 2 . ? O4 Nd1 C7 105.08(15) 4_565 . ? O1 Nd1 C7 162.81(14) 3_666 . ? O2 Nd1 C7 67.82(14) . . ? O6 Nd1 C7 26.70(15) . . ? O3 Nd1 C7 112.42(15) 2_656 . ? O7 Nd1 C7 90.63(15) 2 . ? O8 Nd1 C7 88.68(14) 2 . ? O5 Nd1 C7 27.06(15) . . ? O4 Nd1 C12 114.56(15) 4_565 2 ? O1 Nd1 C12 73.24(14) 3_666 2 ? O2 Nd1 C12 157.91(14) . 2 ? O6 Nd1 C12 84.34(15) . 2 ? O3 Nd1 C12 103.06(14) 2_656 2 ? O7 Nd1 C12 26.41(14) 2 2 ? O8 Nd1 C12 26.61(14) 2 2 ? O5 Nd1 C12 88.76(14) . 2 ? C7 Nd1 C12 90.77(15) . 2 ? O4 Nd1 C6 103.56(15) 4_565 2_656 ? O1 Nd1 C6 62.68(13) 3_666 2_656 ? O2 Nd1 C6 81.05(13) . 2_656 ? O6 Nd1 C6 110.49(14) . 2_656 ? O3 Nd1 C6 23.09(13) 2_656 2_656 ? O7 Nd1 C6 92.36(13) 2 2_656 ? O8 Nd1 C6 129.90(13) 2 2_656 ? O5 Nd1 C6 153.64(13) . 2_656 ? C7 Nd1 C6 131.41(15) . 2_656 ? C12 Nd1 C6 111.55(15) 2 2_656 ? C11 S2 C8 91.5(3) . . ? C1 O1 Nd1 142.6(3) . 3_666 ? C7 O5 Nd1 88.1(3) . . ? C7 O6 Nd1 91.8(3) . . ? C5 C4 C3 111.5(5) . . ? C11 C10 C9 112.0(5) . . ? C8 C9 C10 111.5(5) . . ? C9 C8 C7 125.3(5) . . ? C9 C8 S2 112.2(4) . . ? C7 C8 S2 122.4(4) . . ? O6 C7 O5 123.5(5) . . ? O6 C7 C8 118.9(5) . . ? O5 C7 C8 117.6(5) . . ? O6 C7 Nd1 61.5(3) . . ? O5 C7 Nd1 64.9(3) . . ? C8 C7 Nd1 160.7(4) . . ? C10 C11 C12 125.4(5) . . ? C10 C11 S2 112.7(4) . . ? C12 C11 S2 121.8(4) . . ? C4 C5 C6 129.5(5) . . ? C4 C5 S1 111.4(4) . . ? C6 C5 S1 119.0(4) . . ? C2 C3 C4 113.9(5) . . ? C3 C2 C1 130.1(5) . . ? C3 C2 S1 111.5(4) . . ? C1 C2 S1 118.3(4) . . ? C12 O7 Nd1 92.1(3) . 2_545 ? C6 O3 Nd1 106.5(3) . 2_646 ? C1 O2 Nd1 135.1(3) . . ? C12 O8 Nd1 91.3(3) . 2_545 ? O1 C1 O2 126.8(5) . . ? O1 C1 C2 117.4(5) . . ? O2 C1 C2 115.6(5) . . ? O7 C12 O8 123.3(5) . . ? O7 C12 C11 116.9(5) . . ? O8 C12 C11 119.8(5) . . ? O7 C12 Nd1 61.5(3) . 2_545 ? O8 C12 Nd1 62.0(3) . 2_545 ? C11 C12 Nd1 175.7(4) . 2_545 ? C16 N1 C14 109.9(6) . . ? C16 N1 C13 125.9(6) . . ? C14 N1 C13 124.3(6) . . ? O3 C6 O4 123.8(5) . . ? O3 C6 C5 117.4(5) . . ? O4 C6 C5 118.8(5) . . ? O3 C6 Nd1 50.4(2) . 2_646 ? O4 C6 Nd1 83.4(3) . 2_646 ? C5 C6 Nd1 142.2(4) . 2_646 ? C16 N2 C15 107.6(5) . . ? C16 N2 C17 126.6(5) . . ? C15 N2 C17 125.9(5) . . ? N1 C16 N2 108.7(6) . . ? N2 C17 C18 111.2(5) . . ? C15 C14 N1 105.4(6) . . ? C14 C15 N2 108.5(6) . . ? C2 S1 C5 91.6(3) . . ? C6 O4 Nd1 160.3(4) . 4_566 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.917 _refine_diff_density_min -0.743 _refine_diff_density_rms 0.147 # Attachment '- complex 4.cif' data_complex4 _database_code_depnum_ccdc_archive 'CCDC 822463' #TrackingRef '- complex 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Eu N2 O8 S2' _chemical_formula_weight 603.40 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7636(3) _cell_length_b 16.3609(3) _cell_length_c 11.5890(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.314(3) _cell_angle_gamma 90.00 _cell_volume 2048.34(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5528 _cell_measurement_theta_min 3.1173 _cell_measurement_theta_max 28.9751 _exptl_crystal_description hexagon _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.957 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 3.316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83043 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlis RED' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _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 9266 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3598 _reflns_number_gt 3204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3598 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 0.725 _refine_ls_restrained_S_all 0.725 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Eu1 Eu 0.190224(17) 0.534464(12) 0.575944(18) 0.00857(11) Uani 1 1 d . . . S1 S 0.03995(9) 0.78435(6) 0.69768(10) 0.0133(2) Uani 1 1 d . . . O2 O 0.0414(3) 0.63797(18) 0.5524(3) 0.0161(7) Uani 1 1 d . . . C7 C 0.6763(4) 0.1726(3) 0.7959(4) 0.0142(9) Uani 1 1 d . . . C4 C -0.0545(4) 0.8542(3) 0.7274(4) 0.0143(9) Uani 1 1 d . . . C5 C -0.1771(4) 0.8315(3) 0.6732(4) 0.0175(10) Uani 1 1 d . . . H5A H -0.2414 0.8611 0.6805 0.021 Uiso 1 1 calc R . . C3 C -0.1931(4) 0.7579(3) 0.6053(4) 0.0196(10) Uani 1 1 d . . . H3A H -0.2699 0.7337 0.5622 0.023 Uiso 1 1 calc R . . C2 C -0.0840(4) 0.7256(3) 0.6092(4) 0.0152(9) Uani 1 1 d . . . S2 S 0.52016(10) 0.30129(7) 0.78743(11) 0.0164(3) Uani 1 1 d . . . O3 O -0.0685(3) 0.97599(18) 0.8291(3) 0.0190(7) Uani 1 1 d . . . O4 O 0.1186(3) 0.92921(19) 0.8567(3) 0.0153(7) Uani 1 1 d . . . O10 O 0.3505(3) 0.4472(2) 0.7317(3) 0.0185(7) Uani 1 1 d . . . O1 O -0.1523(3) 0.59870(18) 0.5139(3) 0.0190(7) Uani 1 1 d . . . O6 O 0.6886(3) 0.1592(2) 0.9065(3) 0.0192(7) Uani 1 1 d . . . O5 O 0.7180(3) 0.12291(19) 0.7371(3) 0.0189(7) Uani 1 1 d . . . N2 N -0.3092(5) 0.9684(3) 0.3244(4) 0.0307(12) Uani 1 1 d . . . O9 O 0.3841(3) 0.4908(2) 0.5682(3) 0.0198(7) Uani 1 1 d . . . C20 C -0.2343(5) 1.0333(3) 0.3537(5) 0.0275(13) Uani 1 1 d . . . H20A H -0.1931 1.0539 0.3061 0.033 Uiso 1 1 calc R . . C6 C 0.0025(4) 0.9246(3) 0.8098(4) 0.0114(9) Uani 1 1 d . . . C1 C -0.0649(4) 0.6482(3) 0.5536(4) 0.0132(9) Uani 1 1 d . . . N1 N -0.2284(4) 1.0638(3) 0.4635(4) 0.0224(9) Uani 1 1 d . . . C8 C 0.6137(4) 0.2474(3) 0.7321(4) 0.0127(9) Uani 1 1 d . . . C9 C 0.6221(4) 0.2849(3) 0.6303(4) 0.0174(10) Uani 1 1 d . . . H9A H 0.6677 0.2642 0.5872 0.021 Uiso 1 1 calc R . . C13 C 0.4047(4) 0.4414(3) 0.6578(4) 0.0140(9) Uani 1 1 d . . . C11 C 0.4926(4) 0.3740(3) 0.6721(4) 0.0139(9) Uani 1 1 d . . . C10 C 0.5549(4) 0.3580(3) 0.5980(4) 0.0175(10) Uani 1 1 d . . . H10A H 0.5531 0.3918 0.5328 0.021 Uiso 1 1 calc R . . C25 C -0.1532(5) 1.1332(3) 0.5320(5) 0.0316(12) Uani 1 1 d . . . H25A H -0.1795 1.1495 0.5981 0.038 Uiso 1 1 calc R . . H25B H -0.1668 1.1790 0.4751 0.038 Uiso 1 1 calc R . . C24 C -0.3030(6) 1.0165(4) 0.5023(6) 0.0342(13) Uani 1 1 d . . . H24A H -0.3165 1.0240 0.5755 0.041 Uiso 1 1 calc R . . C23 C -0.3532(6) 0.9578(4) 0.4165(6) 0.0360(14) Uani 1 1 d . . . H23A H -0.4077 0.9173 0.4191 0.043 Uiso 1 1 calc R . . C26 C -0.0156(5) 1.1129(4) 0.5899(5) 0.0366(13) Uani 1 1 d . . . H26A H 0.0301 1.1600 0.6331 0.055 Uiso 1 1 calc R . . H26B H 0.0111 1.0974 0.5247 0.055 Uiso 1 1 calc R . . H26C H -0.0014 1.0686 0.6482 0.055 Uiso 1 1 calc R . . C27 C -0.3357(6) 0.9168(4) 0.2130(6) 0.0480(17) Uani 1 1 d . . . H27A H -0.2933 0.9383 0.1638 0.072 Uiso 1 1 calc R . . H27B H -0.4232 0.9165 0.1635 0.072 Uiso 1 1 calc R . . H27C H -0.3079 0.8621 0.2389 0.072 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.00975(16) 0.00592(16) 0.01082(16) 0.00027(7) 0.00492(11) 0.00026(7) S1 0.0114(5) 0.0098(5) 0.0187(6) -0.0036(4) 0.0059(4) 0.0006(4) O2 0.0161(16) 0.0098(15) 0.0238(17) -0.0004(13) 0.0093(13) 0.0039(13) C7 0.014(2) 0.012(2) 0.017(2) 0.0042(18) 0.0058(18) -0.0009(18) C4 0.020(2) 0.008(2) 0.015(2) -0.0037(17) 0.0072(18) 0.0020(18) C5 0.013(2) 0.016(2) 0.025(2) -0.0054(19) 0.0086(19) 0.0024(18) C3 0.015(2) 0.019(3) 0.023(2) -0.0095(19) 0.0057(19) -0.0051(19) C2 0.013(2) 0.016(2) 0.017(2) -0.0029(18) 0.0060(17) -0.0056(18) S2 0.0193(6) 0.0140(6) 0.0202(6) 0.0058(4) 0.0123(5) 0.0059(5) O3 0.0223(18) 0.0130(17) 0.0266(19) -0.0038(13) 0.0149(15) -0.0006(13) O4 0.0156(16) 0.0164(17) 0.0129(15) -0.0023(13) 0.0044(13) -0.0013(13) O10 0.0190(17) 0.0168(16) 0.0191(17) 0.0034(14) 0.0070(14) 0.0074(14) O1 0.0193(16) 0.0102(16) 0.0274(18) -0.0048(13) 0.0092(14) -0.0018(14) O6 0.0269(18) 0.0208(18) 0.0160(17) 0.0081(13) 0.0150(14) 0.0134(14) O5 0.0282(18) 0.0153(17) 0.0134(15) 0.0006(13) 0.0082(13) 0.0073(14) N2 0.034(3) 0.037(3) 0.019(2) -0.0007(18) 0.009(2) 0.006(2) O9 0.0151(17) 0.0175(17) 0.0284(19) 0.0140(15) 0.0104(14) 0.0074(14) C20 0.030(3) 0.037(4) 0.022(3) 0.005(2) 0.017(2) 0.017(2) C6 0.019(2) 0.011(2) 0.008(2) 0.0018(16) 0.0101(18) 0.0003(18) C1 0.016(2) 0.010(2) 0.016(2) -0.0019(17) 0.0092(18) 0.0003(18) N1 0.029(2) 0.023(2) 0.016(2) 0.0039(17) 0.0108(18) 0.0061(19) C8 0.015(2) 0.010(2) 0.015(2) 0.0006(17) 0.0073(17) 0.0045(17) C9 0.018(2) 0.021(2) 0.018(2) 0.0014(19) 0.0119(19) 0.0065(19) C13 0.013(2) 0.010(2) 0.019(2) 0.0003(18) 0.0074(18) -0.0048(18) C11 0.011(2) 0.014(2) 0.019(2) 0.0041(18) 0.0082(17) -0.0010(17) C10 0.018(2) 0.021(3) 0.016(2) 0.0073(19) 0.0092(19) 0.0058(19) C25 0.042(3) 0.027(3) 0.034(3) 0.002(2) 0.025(3) 0.004(2) C24 0.049(4) 0.032(3) 0.030(3) 0.004(3) 0.026(3) 0.000(3) C23 0.048(4) 0.040(4) 0.026(3) 0.003(2) 0.022(3) -0.004(3) C26 0.040(3) 0.040(3) 0.028(3) 0.002(3) 0.011(2) 0.005(3) C27 0.050(4) 0.060(5) 0.029(3) -0.013(3) 0.010(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O3 2.329(3) 2_546 ? Eu1 O2 2.373(3) . ? Eu1 O1 2.379(3) 3_566 ? Eu1 O4 2.413(3) 4_575 ? Eu1 O9 2.425(3) . ? Eu1 O6 2.451(3) 2_656 ? Eu1 O5 2.470(3) 2_656 ? Eu1 O10 2.482(3) . ? Eu1 C13 2.773(4) . ? Eu1 C7 2.817(4) 2_656 ? Eu1 C6 3.073(4) 4_575 ? Eu1 Eu1 4.2619(4) 3_566 ? S1 C2 1.708(4) . ? S1 C4 1.721(4) . ? O2 C1 1.267(5) . ? C7 O6 1.251(5) . ? C7 O5 1.277(5) . ? C7 C8 1.468(6) . ? C7 Eu1 2.817(4) 2_646 ? C4 C5 1.377(6) . ? C4 C6 1.478(6) . ? C5 C3 1.409(6) . ? C3 C2 1.372(6) . ? C2 C1 1.477(6) . ? S2 C11 1.721(4) . ? S2 C8 1.720(4) . ? O3 C6 1.266(5) . ? O3 Eu1 2.329(3) 2_556 ? O4 C6 1.256(5) . ? O4 Eu1 2.413(3) 4_576 ? O10 C13 1.258(6) . ? O1 C1 1.245(5) . ? O1 Eu1 2.379(3) 3_566 ? O6 Eu1 2.451(3) 2_646 ? O5 Eu1 2.470(3) 2_646 ? N2 C20 1.335(7) . ? N2 C23 1.369(8) . ? N2 C27 1.468(7) . ? O9 C13 1.261(6) . ? C20 N1 1.342(7) . ? C6 Eu1 3.073(4) 4_576 ? N1 C24 1.373(7) . ? N1 C25 1.465(7) . ? C8 C9 1.368(6) . ? C9 C10 1.399(6) . ? C13 C11 1.475(6) . ? C11 C10 1.357(6) . ? C25 C26 1.523(7) . ? C24 C23 1.341(8) . ? 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 Eu1 O2 77.52(10) 2_546 . ? O3 Eu1 O1 77.68(11) 2_546 3_566 ? O2 Eu1 O1 126.95(10) . 3_566 ? O3 Eu1 O4 125.09(11) 2_546 4_575 ? O2 Eu1 O4 76.64(10) . 4_575 ? O1 Eu1 O4 80.68(11) 3_566 4_575 ? O3 Eu1 O9 131.25(11) 2_546 . ? O2 Eu1 O9 150.22(11) . . ? O1 Eu1 O9 74.37(11) 3_566 . ? O4 Eu1 O9 88.59(10) 4_575 . ? O3 Eu1 O6 138.49(10) 2_546 2_656 ? O2 Eu1 O6 78.10(11) . 2_656 ? O1 Eu1 O6 143.21(10) 3_566 2_656 ? O4 Eu1 O6 80.31(10) 4_575 2_656 ? O9 Eu1 O6 73.97(11) . 2_656 ? O3 Eu1 O5 87.88(11) 2_546 2_656 ? O2 Eu1 O5 74.27(11) . 2_656 ? O1 Eu1 O5 149.47(11) 3_566 2_656 ? O4 Eu1 O5 128.93(10) 4_575 2_656 ? O9 Eu1 O5 96.55(11) . 2_656 ? O6 Eu1 O5 53.24(10) 2_656 2_656 ? O3 Eu1 O10 81.47(11) 2_546 . ? O2 Eu1 O10 143.88(11) . . ? O1 Eu1 O10 75.43(11) 3_566 . ? O4 Eu1 O10 139.10(10) 4_575 . ? O9 Eu1 O10 53.32(11) . . ? O6 Eu1 O10 99.75(11) 2_656 . ? O5 Eu1 O10 75.91(11) 2_656 . ? O3 Eu1 C13 105.00(12) 2_546 . ? O2 Eu1 C13 164.01(12) . . ? O1 Eu1 C13 68.57(12) 3_566 . ? O4 Eu1 C13 112.76(12) 4_575 . ? O9 Eu1 C13 27.04(12) . . ? O6 Eu1 C13 90.48(12) 2_656 . ? O5 Eu1 C13 89.95(12) 2_656 . ? O10 Eu1 C13 26.98(12) . . ? O3 Eu1 C7 113.52(12) 2_546 2_656 ? O2 Eu1 C7 73.72(11) . 2_656 ? O1 Eu1 C7 159.13(11) 3_566 2_656 ? O4 Eu1 C7 104.30(12) 4_575 2_656 ? O9 Eu1 C7 85.40(12) . 2_656 ? O6 Eu1 C7 26.32(11) 2_656 2_656 ? O5 Eu1 C7 26.95(11) 2_656 2_656 ? O10 Eu1 C7 88.50(11) . 2_656 ? C13 Eu1 C7 91.06(12) . 2_656 ? O3 Eu1 C6 103.40(11) 2_546 4_575 ? O2 Eu1 C6 61.63(11) . 4_575 ? O1 Eu1 C6 79.88(11) 3_566 4_575 ? O4 Eu1 C6 22.64(10) 4_575 4_575 ? O9 Eu1 C6 109.87(11) . 4_575 ? O6 Eu1 C6 93.75(11) 2_656 4_575 ? O5 Eu1 C6 130.06(11) 2_656 4_575 ? O10 Eu1 C6 153.20(11) . 4_575 ? C13 Eu1 C6 131.15(12) . 4_575 ? C7 Eu1 C6 112.55(12) 2_656 4_575 ? O3 Eu1 Eu1 49.09(9) 2_546 3_566 ? O2 Eu1 Eu1 62.29(7) . 3_566 ? O1 Eu1 Eu1 65.95(7) 3_566 3_566 ? O4 Eu1 Eu1 76.01(7) 4_575 3_566 ? O9 Eu1 Eu1 139.11(9) . 3_566 ? O6 Eu1 Eu1 137.37(8) 2_656 3_566 ? O5 Eu1 Eu1 122.69(7) 2_656 3_566 ? O10 Eu1 Eu1 121.28(8) . 3_566 ? C13 Eu1 Eu1 131.33(9) . 3_566 ? C7 Eu1 Eu1 134.84(8) 2_656 3_566 ? C6 Eu1 Eu1 54.77(8) 4_575 3_566 ? C2 S1 C4 91.6(2) . . ? C1 O2 Eu1 141.2(3) . . ? O6 C7 O5 121.4(4) . . ? O6 C7 C8 119.6(4) . . ? O5 C7 C8 119.0(4) . . ? O6 C7 Eu1 60.3(2) . 2_646 ? O5 C7 Eu1 61.2(2) . 2_646 ? C8 C7 Eu1 176.6(3) . 2_646 ? C5 C4 C6 129.1(4) . . ? C5 C4 S1 111.9(3) . . ? C6 C4 S1 118.9(3) . . ? C4 C5 C3 111.7(4) . . ? C2 C3 C5 113.2(4) . . ? C3 C2 C1 128.1(4) . . ? C3 C2 S1 111.6(3) . . ? C1 C2 S1 120.2(3) . . ? C11 S2 C8 90.9(2) . . ? C6 O3 Eu1 158.2(3) . 2_556 ? C6 O4 Eu1 109.7(2) . 4_576 ? C13 O10 Eu1 89.5(3) . . ? C1 O1 Eu1 137.9(3) . 3_566 ? C7 O6 Eu1 93.4(3) . 2_646 ? C7 O5 Eu1 91.8(2) . 2_646 ? C20 N2 C23 108.5(5) . . ? C20 N2 C27 124.7(5) . . ? C23 N2 C27 126.7(5) . . ? C13 O9 Eu1 92.1(3) . . ? N2 C20 N1 108.6(5) . . ? O4 C6 O3 124.4(4) . . ? O4 C6 C4 117.6(4) . . ? O3 C6 C4 118.0(4) . . ? O4 C6 Eu1 47.69(19) . 4_576 ? O3 C6 Eu1 86.6(2) . 4_576 ? C4 C6 Eu1 141.3(3) . 4_576 ? O1 C1 O2 125.7(4) . . ? O1 C1 C2 118.2(4) . . ? O2 C1 C2 116.0(4) . . ? C20 N1 C24 107.5(5) . . ? C20 N1 C25 126.6(4) . . ? C24 N1 C25 125.9(4) . . ? C9 C8 C7 128.0(4) . . ? C9 C8 S2 111.5(3) . . ? C7 C8 S2 120.5(3) . . ? C8 C9 C10 112.8(4) . . ? O10 C13 O9 121.9(4) . . ? O10 C13 C11 120.1(4) . . ? O9 C13 C11 118.0(4) . . ? O10 C13 Eu1 63.5(2) . . ? O9 C13 Eu1 60.9(2) . . ? C11 C13 Eu1 162.0(3) . . ? C10 C11 C13 127.1(4) . . ? C10 C11 S2 112.0(3) . . ? C13 C11 S2 120.8(3) . . ? C11 C10 C9 112.7(4) . . ? N1 C25 C26 112.2(4) . . ? C23 C24 N1 108.1(5) . . ? C24 C23 N2 107.2(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.894 _refine_diff_density_min -1.432 _refine_diff_density_rms 0.143