# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Xiangjun Zheng' _publ_contact_author_email XJZHENG@BNU.EDU.CN _publ_section_title ; Ligand-directed architecture of europium complexes with sulfobenzenedicarboxylates ; loop_ _publ_author_name 'Xiangjun Zheng' 'Xuebin Deng' 'Lin-Pei Jin' 'Shan-Shan Xiao' ; Shaohua Yan ; # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 762968' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 Eu O9 S' _chemical_formula_weight 431.16 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.00290(10) _cell_length_b 9.43740(10) _cell_length_c 10.47410(10) _cell_angle_alpha 98.2250(10) _cell_angle_beta 94.7590(10) _cell_angle_gamma 107.8410(10) _cell_volume 553.945(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3038 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.57 _exptl_crystal_description flat _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 5.893 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3709 _exptl_absorpt_correction_T_max 0.9434 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4664 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.60 _reflns_number_total 2546 _reflns_number_gt 2374 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2546 _refine_ls_number_parameters 185 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0579 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C1 C 0.4021(7) 0.7372(4) 0.4333(3) 0.0173(8) Uani 1 1 d . . . C2 C 0.5813(7) 0.6872(5) 0.4793(4) 0.0228(8) Uani 1 1 d . . . H2 H 0.6464 0.6311 0.4223 0.027 Uiso 1 1 calc R . . C3 C 0.6638(7) 0.7217(4) 0.6122(4) 0.0197(8) Uani 1 1 d . . . H3 H 0.7835 0.6875 0.6441 0.024 Uiso 1 1 calc R . . C4 C 0.5680(6) 0.8070(4) 0.6972(3) 0.0150(7) Uani 1 1 d . . . C5 C 0.6577(6) 0.8325(4) 0.8404(3) 0.0152(7) Uani 1 1 d . . . C6 C 0.3911(7) 0.8615(4) 0.6484(3) 0.0167(7) Uani 1 1 d . . . C7 C 0.2911(7) 0.9594(4) 0.7341(3) 0.0186(8) Uani 1 1 d . . . C8 C 0.3095(7) 0.8262(4) 0.5156(3) 0.0184(8) Uani 1 1 d . . . H8 H 0.1932 0.8624 0.4823 0.022 Uiso 1 1 calc R . . Eu1 Eu -0.15435(3) 0.827234(19) 0.107597(15) 0.01372(7) Uani 1 1 d . . . O1 O 0.1421(6) 0.7815(4) 0.2476(3) 0.0361(8) Uani 1 1 d . . . O2 O 0.4741(6) 0.7049(4) 0.1909(3) 0.0371(8) Uani 1 1 d . . . O3 O 0.1406(5) 0.5248(3) 0.2479(3) 0.0306(7) Uani 1 1 d . . . O4 O 0.1567(5) 1.0220(3) 0.6848(3) 0.0248(6) Uani 1 1 d . . . O5 O 0.3470(5) 0.9804(3) 0.8577(2) 0.0216(6) Uani 1 1 d . . . O6 O 0.8349(5) 0.9455(3) 0.8915(2) 0.0188(5) Uani 1 1 d . . . O7 O 0.5656(5) 0.7327(3) 0.9052(2) 0.0212(6) Uani 1 1 d . . . O8 O -0.2515(7) 0.5519(4) 0.0751(6) 0.0687(15) Uani 1 1 d D . . O9 O 0.0898(6) 0.7417(4) -0.0371(3) 0.0323(7) Uani 1 1 d D . . S1 S 0.28047(17) 0.68247(11) 0.26755(8) 0.0190(2) Uani 1 1 d . . . H9A H 0.022(14) 0.650(5) -0.096(6) 0.124(17) Uiso 1 1 d D . . H8A H -0.152(11) 0.561(10) 0.156(5) 0.124(17) Uiso 1 1 d D . . H8B H -0.397(8) 0.478(8) 0.085(7) 0.124(17) Uiso 1 1 d D . . H9B H 0.204(11) 0.808(7) -0.074(7) 0.124(17) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0221(19) 0.022(2) 0.0069(15) 0.0011(13) -0.0014(13) 0.0074(15) C2 0.027(2) 0.029(2) 0.0150(18) -0.0002(15) -0.0002(15) 0.0151(17) C3 0.0212(19) 0.024(2) 0.0161(18) 0.0011(15) -0.0022(14) 0.0134(16) C4 0.0154(17) 0.0172(18) 0.0107(16) 0.0016(13) -0.0031(13) 0.0042(14) C5 0.0131(16) 0.0205(19) 0.0124(16) 0.0022(13) 0.0003(13) 0.0065(14) C6 0.0174(17) 0.0232(19) 0.0102(16) 0.0016(14) 0.0014(13) 0.0083(15) C7 0.0207(19) 0.0212(19) 0.0137(17) 0.0014(14) 0.0008(14) 0.0076(15) C8 0.0180(18) 0.025(2) 0.0134(17) 0.0019(14) -0.0001(14) 0.0092(15) Eu1 0.01444(11) 0.01692(11) 0.01000(10) 0.00047(7) -0.00089(6) 0.00684(7) O1 0.057(2) 0.0424(19) 0.0171(14) -0.0039(13) -0.0122(14) 0.0369(17) O2 0.0429(19) 0.049(2) 0.0175(15) 0.0052(13) 0.0139(13) 0.0099(16) O3 0.0349(17) 0.0251(16) 0.0250(15) -0.0017(12) -0.0074(13) 0.0055(13) O4 0.0308(16) 0.0309(16) 0.0164(13) -0.0021(11) -0.0028(11) 0.0199(13) O5 0.0269(14) 0.0316(16) 0.0098(12) 0.0013(11) -0.0001(10) 0.0164(12) O6 0.0181(13) 0.0194(14) 0.0150(12) 0.0009(10) -0.0036(10) 0.0032(10) O7 0.0228(14) 0.0237(15) 0.0135(13) 0.0061(10) -0.0030(10) 0.0023(11) O8 0.0262(19) 0.0206(19) 0.157(5) 0.019(2) 0.005(2) 0.0052(15) O9 0.0408(19) 0.043(2) 0.0261(16) 0.0105(14) 0.0149(14) 0.0281(16) S1 0.0243(5) 0.0257(5) 0.0094(4) 0.0004(3) -0.0011(3) 0.0137(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.379(5) . ? C1 C8 1.384(5) . ? C1 S1 1.765(3) . ? C2 C3 1.395(5) . ? C3 C4 1.391(5) . ? C4 C6 1.404(5) . ? C4 C5 1.511(5) . ? C5 O7 1.257(4) . ? C5 O6 1.266(4) . ? C5 Eu1 2.942(3) 1_656 ? C6 C8 1.393(5) . ? C6 C7 1.488(5) . ? C7 O4 1.256(5) . ? C7 O5 1.282(4) . ? C7 Eu1 2.786(4) 2_576 ? Eu1 O1 2.392(3) . ? Eu1 O6 2.398(3) 2_676 ? Eu1 O9 2.417(3) . ? Eu1 O4 2.426(3) 2_576 ? Eu1 O5 2.436(3) 2_576 ? Eu1 O8 2.448(4) . ? Eu1 O7 2.462(2) 1_454 ? Eu1 O2 2.470(3) 1_455 ? Eu1 O6 2.667(3) 1_454 ? Eu1 C7 2.786(4) 2_576 ? Eu1 C5 2.942(3) 1_454 ? Eu1 Eu1 4.2710(3) 2_575 ? O1 S1 1.453(3) . ? O2 S1 1.447(3) . ? O2 Eu1 2.470(3) 1_655 ? O3 S1 1.442(3) . ? O4 Eu1 2.426(3) 2_576 ? O5 Eu1 2.436(3) 2_576 ? O6 Eu1 2.398(3) 2_676 ? O6 Eu1 2.667(3) 1_656 ? O7 Eu1 2.462(2) 1_656 ? 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 C2 C1 C8 121.3(3) . . ? C2 C1 S1 119.8(3) . . ? C8 C1 S1 118.9(3) . . ? C1 C2 C3 119.3(4) . . ? C4 C3 C2 120.3(4) . . ? C3 C4 C6 119.8(3) . . ? C3 C4 C5 117.1(3) . . ? C6 C4 C5 123.1(3) . . ? O7 C5 O6 120.5(3) . . ? O7 C5 C4 118.6(3) . . ? O6 C5 C4 120.6(3) . . ? O7 C5 Eu1 55.65(17) . 1_656 ? O6 C5 Eu1 65.03(19) . 1_656 ? C4 C5 Eu1 169.4(3) . 1_656 ? C8 C6 C4 119.5(4) . . ? C8 C6 C7 118.6(3) . . ? C4 C6 C7 121.9(3) . . ? O4 C7 O5 121.0(4) . . ? O4 C7 C6 119.9(3) . . ? O5 C7 C6 119.1(3) . . ? O4 C7 Eu1 60.5(2) . 2_576 ? O5 C7 Eu1 60.92(19) . 2_576 ? C6 C7 Eu1 172.8(3) . 2_576 ? C1 C8 C6 119.7(4) . . ? O1 Eu1 O6 80.97(11) . 2_676 ? O1 Eu1 O9 75.07(11) . . ? O6 Eu1 O9 77.22(11) 2_676 . ? O1 Eu1 O4 77.17(10) . 2_576 ? O6 Eu1 O4 78.06(10) 2_676 2_576 ? O9 Eu1 O4 145.19(11) . 2_576 ? O1 Eu1 O5 129.72(9) . 2_576 ? O6 Eu1 O5 78.11(10) 2_676 2_576 ? O9 Eu1 O5 140.87(10) . 2_576 ? O4 Eu1 O5 54.03(9) 2_576 2_576 ? O1 Eu1 O8 74.46(13) . . ? O6 Eu1 O8 141.96(12) 2_676 . ? O9 Eu1 O8 68.73(15) . . ? O4 Eu1 O8 122.65(16) 2_576 . ? O5 Eu1 O8 139.80(12) 2_576 . ? O1 Eu1 O7 145.89(10) . 1_454 ? O6 Eu1 O7 115.46(9) 2_676 1_454 ? O9 Eu1 O7 79.73(10) . 1_454 ? O4 Eu1 O7 133.55(10) 2_576 1_454 ? O5 Eu1 O7 84.08(9) 2_576 1_454 ? O8 Eu1 O7 75.18(14) . 1_454 ? O1 Eu1 O2 103.90(12) . 1_455 ? O6 Eu1 O2 147.65(10) 2_676 1_455 ? O9 Eu1 O2 135.11(12) . 1_455 ? O4 Eu1 O2 72.13(10) 2_576 1_455 ? O5 Eu1 O2 74.41(11) 2_576 1_455 ? O8 Eu1 O2 67.97(14) . 1_455 ? O7 Eu1 O2 78.45(10) 1_454 1_455 ? O1 Eu1 O6 135.66(10) . 1_454 ? O6 Eu1 O6 65.13(9) 2_676 1_454 ? O9 Eu1 O6 70.36(10) . 1_454 ? O4 Eu1 O6 119.42(9) 2_576 1_454 ? O5 Eu1 O6 71.85(8) 2_576 1_454 ? O8 Eu1 O6 115.79(15) . 1_454 ? O7 Eu1 O6 50.37(8) 1_454 1_454 ? O2 Eu1 O6 120.12(10) 1_455 1_454 ? O1 Eu1 C7 103.62(11) . 2_576 ? O6 Eu1 C7 78.41(10) 2_676 2_576 ? O9 Eu1 C7 155.48(12) . 2_576 ? O4 Eu1 C7 26.76(10) 2_576 2_576 ? O5 Eu1 C7 27.38(10) 2_576 2_576 ? O8 Eu1 C7 135.21(15) . 2_576 ? O7 Eu1 C7 108.78(10) 1_454 2_576 ? O2 Eu1 C7 69.34(11) 1_455 2_576 ? O6 Eu1 C7 96.89(10) 1_454 2_576 ? O1 Eu1 C5 147.59(11) . 1_454 ? O6 Eu1 C5 90.54(9) 2_676 1_454 ? O9 Eu1 C5 72.55(10) . 1_454 ? O4 Eu1 C5 131.74(10) 2_576 1_454 ? O5 Eu1 C5 77.81(9) 2_576 1_454 ? O8 Eu1 C5 94.87(15) . 1_454 ? O7 Eu1 C5 24.92(9) 1_454 1_454 ? O2 Eu1 C5 99.91(10) 1_455 1_454 ? O6 Eu1 C5 25.49(9) 1_454 1_454 ? C7 Eu1 C5 105.18(11) 2_576 1_454 ? O1 Eu1 Eu1 111.01(9) . 2_575 ? O6 Eu1 Eu1 34.51(6) 2_676 2_575 ? O9 Eu1 Eu1 70.48(8) . 2_575 ? O4 Eu1 Eu1 100.99(7) 2_576 2_575 ? O5 Eu1 Eu1 71.93(7) 2_576 2_575 ? O8 Eu1 Eu1 135.55(14) . 2_575 ? O7 Eu1 Eu1 80.96(6) 1_454 2_575 ? O2 Eu1 Eu1 141.96(8) 1_455 2_575 ? O6 Eu1 Eu1 30.62(5) 1_454 2_575 ? C7 Eu1 Eu1 87.83(8) 2_576 2_575 ? C5 Eu1 Eu1 56.05(7) 1_454 2_575 ? S1 O1 Eu1 146.11(18) . . ? S1 O2 Eu1 160.7(2) . 1_655 ? C7 O4 Eu1 92.8(2) . 2_576 ? C7 O5 Eu1 91.7(2) . 2_576 ? C5 O6 Eu1 155.2(2) . 2_676 ? C5 O6 Eu1 89.5(2) . 1_656 ? Eu1 O6 Eu1 114.87(9) 2_676 1_656 ? C5 O7 Eu1 99.4(2) . 1_656 ? O3 S1 O2 110.9(2) . . ? O3 S1 O1 113.5(2) . . ? O2 S1 O1 112.4(2) . . ? O3 S1 C1 107.23(18) . . ? O2 S1 C1 107.79(19) . . ? O1 S1 C1 104.65(18) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.410 _refine_diff_density_min -0.758 _refine_diff_density_rms 0.149 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 762969' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H13 Eu N2 O8 S' _chemical_formula_weight 593.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.96050(10) _cell_length_b 17.6633(2) _cell_length_c 15.9655(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.5850(10) _cell_angle_gamma 90.00 _cell_volume 1962.78(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4340 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 27.62 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.008 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 3.356 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6508 _exptl_absorpt_correction_T_max 0.9359 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9492 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.64 _reflns_number_total 4508 _reflns_number_gt 3800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0249P)^2^+1.4184P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4508 _refine_ls_number_parameters 296 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0578 _refine_ls_wR_factor_gt 0.0545 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 C1 C 0.5002(5) 0.47865(18) 0.32248(19) 0.0197(7) Uani 1 1 d . . . C2 C 0.5175(4) 0.39817(18) 0.2935(2) 0.0184(6) Uani 1 1 d . . . C3 C 0.5501(4) 0.33875(18) 0.34981(19) 0.0170(6) Uani 1 1 d . . . C4 C 0.5514(5) 0.34794(18) 0.4429(2) 0.0183(6) Uani 1 1 d . . . C5 C 0.5748(4) 0.26549(18) 0.3189(2) 0.0183(6) Uani 1 1 d . . . H5A H 0.5995 0.2257 0.3555 0.022 Uiso 1 1 calc R . . C6 C 0.5624(4) 0.25230(17) 0.23360(19) 0.0172(6) Uani 1 1 d . . . C7 C 0.5297(5) 0.31095(19) 0.1782(2) 0.0224(7) Uani 1 1 d . . . H7A H 0.5227 0.3016 0.1209 0.027 Uiso 1 1 calc R . . C8 C 0.5073(5) 0.38375(19) 0.2083(2) 0.0229(7) Uani 1 1 d . . . H8A H 0.4852 0.4234 0.1710 0.027 Uiso 1 1 calc R . . C9 C 0.4515(7) 0.8221(2) 0.4304(3) 0.0404(10) Uani 1 1 d . . . H9A H 0.4426 0.8013 0.4837 0.048 Uiso 1 1 calc R . . C10 C 0.4782(8) 0.9003(3) 0.4237(3) 0.0538(13) Uani 1 1 d . . . H10A H 0.4842 0.9304 0.4714 0.065 Uiso 1 1 calc R . . C11 C 0.4953(6) 0.9318(2) 0.3463(3) 0.0444(11) Uani 1 1 d . . . H11A H 0.5163 0.9835 0.3407 0.053 Uiso 1 1 calc R . . C12 C 0.4811(5) 0.8859(2) 0.2758(3) 0.0309(9) Uani 1 1 d . . . C13 C 0.4901(5) 0.9158(2) 0.1931(3) 0.0337(9) Uani 1 1 d . . . H13A H 0.5107 0.9674 0.1855 0.040 Uiso 1 1 calc R . . C14 C 0.4692(5) 0.8708(2) 0.1261(3) 0.0348(9) Uani 1 1 d . . . H14A H 0.4760 0.8915 0.0727 0.042 Uiso 1 1 calc R . . C15 C 0.4365(5) 0.7912(2) 0.1356(2) 0.0265(8) Uani 1 1 d . . . C16 C 0.4097(6) 0.7439(2) 0.0669(2) 0.0396(10) Uani 1 1 d . . . H16A H 0.4120 0.7633 0.0128 0.047 Uiso 1 1 calc R . . C17 C 0.3801(7) 0.6690(2) 0.0800(2) 0.0440(11) Uani 1 1 d . . . H17A H 0.3609 0.6366 0.0348 0.053 Uiso 1 1 calc R . . C18 C 0.3787(6) 0.6408(2) 0.1618(2) 0.0362(9) Uani 1 1 d . . . H18A H 0.3584 0.5892 0.1694 0.043 Uiso 1 1 calc R . . C19 C 0.4514(5) 0.80735(19) 0.2880(2) 0.0228(7) Uani 1 1 d . . . C20 C 0.4316(4) 0.75905(19) 0.2161(2) 0.0216(7) Uani 1 1 d . . . Eu1 Eu 0.41814(2) 0.626359(9) 0.381972(9) 0.01430(5) Uani 1 1 d . . . N1 N 0.4382(4) 0.77611(16) 0.36544(19) 0.0259(6) Uani 1 1 d . . . N2 N 0.4045(4) 0.68348(16) 0.22900(18) 0.0239(6) Uani 1 1 d . . . O1 O 0.6069(3) 0.50358(12) 0.37971(14) 0.0226(5) Uani 1 1 d . . . O2 O 0.3770(4) 0.52045(13) 0.28678(15) 0.0283(6) Uani 1 1 d . . . O3 O 0.4184(3) 0.38422(13) 0.47818(14) 0.0222(5) Uani 1 1 d . . . O4 O 0.6838(3) 0.31758(13) 0.48493(14) 0.0269(5) Uani 1 1 d . . . O5 O 0.6019(4) 0.10875(14) 0.26491(16) 0.0377(7) Uani 1 1 d . . . O6 O 0.4156(3) 0.14761(14) 0.14265(16) 0.0289(6) Uani 1 1 d . . . O7 O 0.7568(3) 0.16079(13) 0.14298(16) 0.0279(5) Uani 1 1 d . . . O8 O 0.2383(3) 0.52772(13) 0.46219(15) 0.0264(5) Uani 1 1 d D . . S1 S 0.58597(11) 0.15872(4) 0.19510(5) 0.01878(17) Uani 1 1 d . . . H8C H 0.252(8) 0.529(3) 0.5207(13) 0.097(15) Uiso 1 1 d D . . H8D H 0.246(8) 0.4761(14) 0.448(3) 0.097(15) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0269(17) 0.0162(16) 0.0161(15) 0.0024(12) 0.0054(13) -0.0008(13) C2 0.0182(15) 0.0180(16) 0.0190(16) -0.0015(13) 0.0017(12) -0.0004(12) C3 0.0156(15) 0.0182(16) 0.0171(15) -0.0027(13) 0.0020(12) -0.0009(12) C4 0.0270(17) 0.0113(15) 0.0166(15) 0.0013(12) -0.0008(13) -0.0035(13) C5 0.0192(16) 0.0167(16) 0.0191(16) -0.0003(13) 0.0010(12) 0.0017(12) C6 0.0159(15) 0.0158(16) 0.0198(16) -0.0037(12) 0.0012(12) 0.0004(12) C7 0.0312(19) 0.0226(18) 0.0133(15) -0.0024(13) -0.0034(13) 0.0019(14) C8 0.0323(18) 0.0188(18) 0.0176(16) 0.0030(13) 0.0004(13) 0.0027(14) C9 0.068(3) 0.023(2) 0.030(2) -0.0038(17) -0.005(2) -0.0015(19) C10 0.084(4) 0.028(2) 0.050(3) -0.011(2) -0.005(3) -0.001(2) C11 0.055(3) 0.020(2) 0.058(3) 0.004(2) -0.004(2) -0.0030(18) C12 0.0231(18) 0.022(2) 0.048(2) 0.0077(17) -0.0031(16) 0.0015(14) C13 0.0242(19) 0.024(2) 0.053(3) 0.0164(18) 0.0030(17) 0.0018(15) C14 0.0233(18) 0.037(2) 0.045(2) 0.023(2) 0.0049(16) 0.0042(16) C15 0.0189(17) 0.032(2) 0.0289(19) 0.0137(15) 0.0035(14) 0.0052(14) C16 0.049(3) 0.047(3) 0.0224(19) 0.0102(18) -0.0004(17) 0.000(2) C17 0.068(3) 0.040(3) 0.024(2) 0.0002(18) -0.003(2) -0.004(2) C18 0.057(3) 0.027(2) 0.0246(19) 0.0002(16) -0.0033(18) -0.0008(18) C19 0.0183(16) 0.0170(17) 0.0331(19) 0.0053(14) -0.0026(14) 0.0019(13) C20 0.0140(15) 0.0234(18) 0.0275(18) 0.0066(14) -0.0002(13) 0.0029(13) Eu1 0.01547(8) 0.01250(9) 0.01493(8) 0.00088(6) -0.00047(5) 0.00051(6) N1 0.0281(16) 0.0175(15) 0.0318(17) 0.0033(12) -0.0013(13) -0.0002(12) N2 0.0271(15) 0.0211(15) 0.0235(15) 0.0043(12) -0.0004(12) 0.0005(12) O1 0.0270(12) 0.0166(12) 0.0241(12) -0.0051(9) -0.0016(10) -0.0015(9) O2 0.0400(15) 0.0167(12) 0.0280(13) -0.0010(10) -0.0116(11) 0.0066(10) O3 0.0214(11) 0.0256(13) 0.0196(11) -0.0038(10) 0.0030(9) 0.0031(10) O4 0.0336(14) 0.0292(14) 0.0179(12) -0.0007(10) -0.0004(10) 0.0133(11) O5 0.066(2) 0.0169(13) 0.0300(14) 0.0003(11) -0.0022(13) 0.0029(12) O6 0.0184(12) 0.0302(14) 0.0382(15) -0.0124(11) -0.0030(11) -0.0024(10) O7 0.0181(12) 0.0264(13) 0.0393(15) -0.0117(11) 0.0064(10) 0.0016(10) O8 0.0288(13) 0.0223(13) 0.0281(13) 0.0044(11) -0.0003(11) -0.0015(10) S1 0.0183(4) 0.0155(4) 0.0226(4) -0.0060(3) -0.0007(3) -0.0002(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 C1 O1 1.251(4) . ? C1 O2 1.263(4) . ? C1 C2 1.500(4) . ? C1 Eu1 2.837(3) . ? C2 C8 1.385(4) . ? C2 C3 1.399(4) . ? C3 C5 1.396(4) . ? C3 C4 1.496(4) . ? C4 O4 1.255(4) . ? C4 O3 1.263(4) . ? C4 Eu1 2.838(3) 3_666 ? C5 C6 1.383(4) . ? C5 H5A 0.9300 . ? C6 C7 1.380(4) . ? C6 S1 1.772(3) . ? C7 C8 1.382(4) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 N1 1.320(5) . ? C9 C10 1.398(6) . ? C9 H9A 0.9300 . ? C10 C11 1.361(6) . ? C10 H10A 0.9300 . ? C11 C12 1.390(6) . ? C11 H11A 0.9300 . ? C12 C19 1.416(5) . ? C12 C13 1.425(5) . ? C13 C14 1.340(6) . ? C13 H13A 0.9300 . ? C14 C15 1.431(5) . ? C14 H14A 0.9300 . ? C15 C16 1.391(5) . ? C15 C20 1.406(5) . ? C16 C17 1.355(6) . ? C16 H16A 0.9300 . ? C17 C18 1.398(5) . ? C17 H17A 0.9300 . ? C18 N2 1.322(4) . ? C18 H18A 0.9300 . ? C19 N1 1.358(4) . ? C19 C20 1.436(5) . ? C20 N2 1.364(4) . ? Eu1 O7 2.380(2) 2_655 ? Eu1 O6 2.382(2) 2 ? Eu1 O2 2.425(2) . ? Eu1 O4 2.456(2) 3_666 ? Eu1 O3 2.502(2) 3_666 ? Eu1 O8 2.505(2) . ? Eu1 O1 2.536(2) . ? Eu1 N2 2.643(3) . ? Eu1 N1 2.662(3) . ? Eu1 C4 2.838(3) 3_666 ? O3 Eu1 2.502(2) 3_666 ? O4 Eu1 2.456(2) 3_666 ? O5 S1 1.425(3) . ? O6 S1 1.458(2) . ? O6 Eu1 2.382(2) 2_545 ? O7 S1 1.459(2) . ? O7 Eu1 2.380(2) 2_645 ? O8 H8C 0.938(19) . ? O8 H8D 0.941(19) . ? 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 C1 O2 121.3(3) . . ? O1 C1 C2 120.7(3) . . ? O2 C1 C2 118.1(3) . . ? O1 C1 Eu1 63.38(17) . . ? O2 C1 Eu1 58.36(16) . . ? C2 C1 Eu1 172.7(2) . . ? C8 C2 C3 120.0(3) . . ? C8 C2 C1 118.3(3) . . ? C3 C2 C1 121.7(3) . . ? C5 C3 C2 119.2(3) . . ? C5 C3 C4 116.9(3) . . ? C2 C3 C4 123.8(3) . . ? O4 C4 O3 121.1(3) . . ? O4 C4 C3 118.8(3) . . ? O3 C4 C3 120.1(3) . . ? O4 C4 Eu1 59.66(16) . 3_666 ? O3 C4 Eu1 61.81(16) . 3_666 ? C3 C4 Eu1 175.1(2) . 3_666 ? C6 C5 C3 119.9(3) . . ? C6 C5 H5A 120.1 . . ? C3 C5 H5A 120.1 . . ? C7 C6 C5 120.9(3) . . ? C7 C6 S1 119.6(2) . . ? C5 C6 S1 119.6(2) . . ? C6 C7 C8 119.6(3) . . ? C6 C7 H7A 120.2 . . ? C8 C7 H7A 120.2 . . ? C7 C8 C2 120.5(3) . . ? C7 C8 H8A 119.7 . . ? C2 C8 H8A 119.7 . . ? N1 C9 C10 123.8(4) . . ? N1 C9 H9A 118.1 . . ? C10 C9 H9A 118.1 . . ? C11 C10 C9 119.1(4) . . ? C11 C10 H10A 120.5 . . ? C9 C10 H10A 120.5 . . ? C10 C11 C12 119.4(4) . . ? C10 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C11 C12 C19 118.0(4) . . ? C11 C12 C13 122.0(4) . . ? C19 C12 C13 119.9(4) . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C15 121.0(4) . . ? C13 C14 H14A 119.5 . . ? C15 C14 H14A 119.5 . . ? C16 C15 C20 118.3(3) . . ? C16 C15 C14 121.8(3) . . ? C20 C15 C14 119.9(4) . . ? C17 C16 C15 119.0(4) . . ? C17 C16 H16A 120.5 . . ? C15 C16 H16A 120.5 . . ? C16 C17 C18 119.6(4) . . ? C16 C17 H17A 120.2 . . ? C18 C17 H17A 120.2 . . ? N2 C18 C17 123.6(4) . . ? N2 C18 H18A 118.2 . . ? C17 C18 H18A 118.2 . . ? N1 C19 C12 122.3(3) . . ? N1 C19 C20 118.6(3) . . ? C12 C19 C20 119.0(3) . . ? N2 C20 C15 122.5(3) . . ? N2 C20 C19 118.3(3) . . ? C15 C20 C19 119.2(3) . . ? O7 Eu1 O6 149.23(8) 2_655 2 ? O7 Eu1 O2 101.45(9) 2_655 . ? O6 Eu1 O2 84.81(9) 2 . ? O7 Eu1 O4 108.99(9) 2_655 3_666 ? O6 Eu1 O4 77.83(8) 2 3_666 ? O2 Eu1 O4 145.07(9) . 3_666 ? O7 Eu1 O3 75.18(8) 2_655 3_666 ? O6 Eu1 O3 126.35(8) 2 3_666 ? O2 Eu1 O3 123.45(7) . 3_666 ? O4 Eu1 O3 52.47(7) 3_666 3_666 ? O7 Eu1 O8 138.08(8) 2_655 . ? O6 Eu1 O8 72.68(8) 2 . ? O2 Eu1 O8 74.19(8) . . ? O4 Eu1 O8 71.80(8) 3_666 . ? O3 Eu1 O8 73.56(8) 3_666 . ? O7 Eu1 O1 73.90(8) 2_655 . ? O6 Eu1 O1 129.57(8) 2 . ? O2 Eu1 O1 52.36(7) . . ? O4 Eu1 O1 120.76(7) 3_666 . ? O3 Eu1 O1 73.62(7) 3_666 . ? O8 Eu1 O1 70.99(8) . . ? O7 Eu1 N2 76.89(8) 2_655 . ? O6 Eu1 N2 76.20(8) 2 . ? O2 Eu1 N2 73.29(8) . . ? O4 Eu1 N2 129.61(8) 3_666 . ? O3 Eu1 N2 149.84(8) 3_666 . ? O8 Eu1 N2 136.41(8) . . ? O1 Eu1 N2 109.09(8) . . ? O7 Eu1 N1 71.25(8) 2_655 . ? O6 Eu1 N1 83.06(8) 2 . ? O2 Eu1 N1 135.26(8) . . ? O4 Eu1 N1 72.61(9) 3_666 . ? O3 Eu1 N1 97.98(8) 3_666 . ? O8 Eu1 N1 140.24(9) . . ? O1 Eu1 N1 145.14(8) . . ? N2 Eu1 N1 62.00(9) . . ? O7 Eu1 C1 89.08(9) 2_655 . ? O6 Eu1 C1 106.81(9) 2 . ? O2 Eu1 C1 26.31(8) . . ? O4 Eu1 C1 136.19(8) 3_666 . ? O3 Eu1 C1 97.98(8) 3_666 . ? O8 Eu1 C1 68.59(8) . . ? O1 Eu1 C1 26.18(8) . . ? N2 Eu1 C1 92.70(9) . . ? N1 Eu1 C1 150.43(9) . . ? O7 Eu1 C4 93.58(9) 2_655 3_666 ? O6 Eu1 C4 101.55(9) 2 3_666 ? O2 Eu1 C4 138.40(8) . 3_666 ? O4 Eu1 C4 26.17(8) 3_666 3_666 ? O3 Eu1 C4 26.40(8) 3_666 3_666 ? O8 Eu1 C4 68.92(8) . 3_666 ? O1 Eu1 C4 96.74(8) . 3_666 ? N2 Eu1 C4 148.29(9) . 3_666 ? N1 Eu1 C4 86.29(9) . 3_666 ? C1 Eu1 C4 117.63(9) . 3_666 ? C9 N1 C19 117.4(3) . . ? C9 N1 Eu1 122.5(2) . . ? C19 N1 Eu1 119.9(2) . . ? C18 N2 C20 117.0(3) . . ? C18 N2 Eu1 122.4(2) . . ? C20 N2 Eu1 120.6(2) . . ? C1 O1 Eu1 90.44(19) . . ? C1 O2 Eu1 95.33(19) . . ? C4 O3 Eu1 91.79(18) . 3_666 ? C4 O4 Eu1 94.17(19) . 3_666 ? S1 O6 Eu1 154.45(16) . 2_545 ? S1 O7 Eu1 150.55(16) . 2_645 ? Eu1 O8 H8C 117(3) . . ? Eu1 O8 H8D 122(3) . . ? H8C O8 H8D 105(3) . . ? O5 S1 O6 114.98(16) . . ? O5 S1 O7 113.84(16) . . ? O6 S1 O7 109.80(15) . . ? O5 S1 C6 108.25(15) . . ? O6 S1 C6 104.30(14) . . ? O7 S1 C6 104.68(14) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.64 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.040 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.107 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 762970' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 Eu N2 O9 S' _chemical_formula_weight 611.36 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 'Cc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.2533(8) _cell_length_b 16.2583(13) _cell_length_c 12.0825(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.909(2) _cell_angle_gamma 90.00 _cell_volume 1999.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 3.301 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6735 _exptl_absorpt_correction_T_max 0.9369 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4504 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2155 _reflns_number_gt 2020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+8.1440P] 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 contr _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 0.51(3) _refine_ls_number_reflns 2155 _refine_ls_number_parameters 298 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 C1 C 0.3960(12) 0.1354(7) 0.1276(9) 0.024(3) Uani 1 1 d . . . C2 C 0.4648(12) 0.2093(7) 0.0863(9) 0.024(3) Uani 1 1 d . . . C3 C 0.5674(13) 0.1989(6) 0.0235(10) 0.029(3) Uani 1 1 d . . . H3A H 0.5964 0.1462 0.0090 0.034 Uiso 1 1 calc R . . C4 C 0.6276(12) 0.2668(6) -0.0182(9) 0.026(3) Uani 1 1 d . . . H4A H 0.6947 0.2592 -0.0626 0.032 Uiso 1 1 calc R . . C5 C 0.5885(11) 0.3461(6) 0.0059(8) 0.021(2) Uani 1 1 d . . . C6 C 0.6634(12) 0.4173(6) -0.0390(9) 0.025(3) Uani 1 1 d . . . C7 C 0.4860(11) 0.3561(6) 0.0724(8) 0.022(2) Uani 1 1 d . . . C8 C 0.4244(12) 0.2872(6) 0.1092(9) 0.021(2) Uani 1 1 d . . . H8A H 0.3541 0.2940 0.1503 0.025 Uiso 1 1 calc R . . C9 C 0.4930(13) -0.1312(8) 0.1603(11) 0.039(3) Uani 1 1 d . . . H9A H 0.5261 -0.0834 0.1320 0.047 Uiso 1 1 calc R . . C10 C 0.5589(14) -0.2031(9) 0.1492(11) 0.044(4) Uani 1 1 d . . . H10A H 0.6373 -0.2035 0.1176 0.053 Uiso 1 1 calc R . . C11 C 0.5078(15) -0.2743(8) 0.1851(12) 0.048(4) Uani 1 1 d . . . H11A H 0.5497 -0.3240 0.1749 0.058 Uiso 1 1 calc R . . C12 C 0.3915(14) -0.2735(8) 0.2376(10) 0.040(4) Uani 1 1 d . . . C13 C 0.3299(17) -0.3454(8) 0.2743(11) 0.048(4) Uani 1 1 d . . . H13A H 0.3679 -0.3966 0.2657 0.058 Uiso 1 1 calc R . . C14 C 0.2183(17) -0.3405(8) 0.3209(11) 0.045(4) Uani 1 1 d . . . H14A H 0.1800 -0.3884 0.3439 0.055 Uiso 1 1 calc R . . C15 C 0.1574(15) -0.2640(7) 0.3361(9) 0.034(3) Uani 1 1 d . . . C16 C 0.0406(15) -0.2548(8) 0.3838(10) 0.038(3) Uani 1 1 d . . . H16A H -0.0034 -0.3011 0.4053 0.046 Uiso 1 1 calc R . . C17 C -0.0089(15) -0.1790(7) 0.3989(10) 0.038(3) Uani 1 1 d . . . H17A H -0.0855 -0.1727 0.4321 0.046 Uiso 1 1 calc R . . C18 C 0.0562(13) -0.1111(8) 0.3641(10) 0.033(3) Uani 1 1 d . . . H18A H 0.0217 -0.0593 0.3756 0.039 Uiso 1 1 calc R . . C19 C 0.3319(13) -0.1961(6) 0.2485(9) 0.028(3) Uani 1 1 d . . . C20 C 0.2156(12) -0.1908(7) 0.3005(8) 0.024(3) Uani 1 1 d . . . Eu1 Eu 0.25998(9) 0.00741(2) 0.21918(8) 0.01966(16) Uani 1 1 d . . . N1 N 0.3837(11) -0.1258(6) 0.2098(8) 0.032(2) Uani 1 1 d . . . N2 N 0.1653(10) -0.1157(5) 0.3151(8) 0.024(2) Uani 1 1 d . . . O1 O 0.4409(9) 0.0649(5) 0.1252(8) 0.033(2) Uani 1 1 d . . . O2 O 0.2897(10) 0.1487(5) 0.1696(8) 0.041(2) Uani 1 1 d . . . O3 O 0.7232(9) 0.4657(5) 0.0283(6) 0.0311(19) Uani 1 1 d . . . O4 O 0.6606(9) 0.4201(5) -0.1416(6) 0.0252(18) Uani 1 1 d . . . O5 O 0.5242(9) 0.5027(4) 0.1618(7) 0.033(2) Uani 1 1 d . . . O6 O 0.3099(9) 0.4419(5) 0.1565(8) 0.040(2) Uani 1 1 d . . . O7 O 0.3873(9) 0.4913(4) -0.0109(7) 0.034(2) Uani 1 1 d . . . O8 O 0.4269(9) 0.0109(5) 0.3729(7) 0.039(2) Uani 1 1 d . . . H8D H 0.3868 0.0105 0.4305 0.047 Uiso 1 1 d R . . H8E H 0.5018 -0.0115 0.3889 0.047 Uiso 1 1 d R . . S1 S 0.4212(3) 0.45520(17) 0.0972(2) 0.0225(6) Uani 1 1 d . . . O9 O 0.6710(10) 0.9508(6) 0.3569(8) 0.043(2) Uani 1 1 d . . . H9D H 0.7013 0.9458 0.2948 0.051 Uiso 1 1 d R . . H9E H 0.7320 0.9692 0.4043 0.051 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 C1 0.016(7) 0.030(6) 0.030(6) 0.000(5) 0.012(5) -0.005(5) C2 0.019(7) 0.032(6) 0.023(5) -0.003(4) 0.011(5) -0.004(5) C3 0.034(8) 0.017(5) 0.037(6) 0.001(5) 0.014(6) -0.001(5) C4 0.027(8) 0.027(6) 0.030(6) 0.003(5) 0.022(6) 0.000(5) C5 0.020(7) 0.020(5) 0.022(5) 0.004(4) 0.004(5) -0.006(5) C6 0.018(6) 0.022(5) 0.035(6) 0.000(5) 0.005(5) 0.008(5) C7 0.019(7) 0.024(5) 0.022(5) 0.003(4) 0.001(5) -0.003(5) C8 0.013(6) 0.028(6) 0.024(5) 0.008(4) 0.010(5) 0.000(5) C9 0.023(8) 0.044(8) 0.049(8) -0.005(6) 0.002(7) 0.004(6) C10 0.021(8) 0.058(9) 0.050(8) -0.012(7) -0.004(6) 0.015(7) C11 0.049(10) 0.037(7) 0.056(8) -0.015(6) -0.002(8) 0.026(7) C12 0.043(9) 0.043(8) 0.031(6) -0.003(5) -0.004(6) 0.022(7) C13 0.071(12) 0.019(6) 0.052(8) -0.001(5) -0.004(8) 0.004(7) C14 0.058(11) 0.026(6) 0.050(8) 0.010(6) -0.005(8) -0.002(7) C15 0.053(10) 0.019(6) 0.030(6) 0.005(5) -0.001(6) -0.002(6) C16 0.045(10) 0.040(7) 0.031(6) 0.013(5) 0.008(6) -0.018(7) C17 0.047(9) 0.033(7) 0.038(7) 0.011(5) 0.019(7) -0.007(6) C18 0.026(8) 0.037(7) 0.035(7) 0.001(5) 0.004(6) 0.001(6) C19 0.035(8) 0.019(6) 0.029(6) -0.004(4) 0.001(5) 0.002(5) C20 0.023(7) 0.029(6) 0.020(5) 0.001(4) 0.000(5) 0.007(5) Eu1 0.0226(3) 0.0163(2) 0.0212(2) -0.0002(4) 0.00733(17) -0.0002(5) N1 0.029(7) 0.030(5) 0.036(6) -0.002(4) 0.001(5) 0.002(5) N2 0.020(6) 0.022(5) 0.031(5) -0.004(4) 0.007(5) 0.003(4) O1 0.022(5) 0.022(4) 0.057(5) 0.001(4) 0.019(4) 0.002(4) O2 0.034(6) 0.020(4) 0.073(6) 0.006(4) 0.025(5) -0.004(4) O3 0.034(5) 0.029(4) 0.030(4) -0.004(3) 0.003(4) -0.009(4) O4 0.031(5) 0.032(4) 0.015(4) 0.002(3) 0.012(3) -0.008(4) O5 0.029(5) 0.024(4) 0.043(5) -0.007(3) -0.005(4) -0.003(3) O6 0.029(6) 0.030(5) 0.065(6) 0.004(4) 0.027(5) 0.000(4) O7 0.031(6) 0.029(4) 0.043(5) 0.006(3) 0.004(4) 0.005(4) O8 0.024(5) 0.059(6) 0.034(5) -0.008(4) 0.004(4) 0.014(4) S1 0.0188(16) 0.0187(13) 0.0313(14) 0.0005(11) 0.0079(13) 0.0020(13) O9 0.028(6) 0.055(6) 0.047(5) -0.005(5) 0.011(5) -0.009(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.236(14) . ? C1 O2 1.275(15) . ? C1 C2 1.509(16) . ? C1 Eu1 2.805(11) . ? C2 C8 1.372(16) . ? C2 C3 1.379(17) . ? C3 C4 1.389(15) . ? C3 H3A 0.9300 . ? C4 C5 1.392(15) . ? C4 H4A 0.9300 . ? C5 C7 1.407(16) . ? C5 C6 1.525(15) . ? C6 O4 1.237(13) . ? C6 O3 1.240(13) . ? C7 C8 1.385(15) . ? C7 S1 1.782(11) . ? C8 H8A 0.9300 . ? C9 N1 1.335(17) . ? C9 C10 1.365(18) . ? C9 H9A 0.9300 . ? C10 C11 1.36(2) . ? C10 H10A 0.9300 . ? C11 C12 1.42(2) . ? C11 H11A 0.9300 . ? C12 C19 1.413(16) . ? C12 C13 1.42(2) . ? C13 C14 1.34(2) . ? C13 H13A 0.9300 . ? C14 C15 1.413(18) . ? C14 H14A 0.9300 . ? C15 C16 1.40(2) . ? C15 C20 1.421(16) . ? C16 C17 1.354(18) . ? C16 H16A 0.9300 . ? C17 C18 1.382(17) . ? C17 H17A 0.9300 . ? C18 N2 1.330(16) . ? C18 H18A 0.9300 . ? C19 N1 1.366(15) . ? C19 C20 1.416(17) . ? C20 N2 1.345(14) . ? Eu1 O8 2.371(9) . ? Eu1 O4 2.382(7) 4_455 ? Eu1 O3 2.390(8) 3_445 ? Eu1 O2 2.403(7) . ? Eu1 O5 2.435(9) 3_445 ? Eu1 O1 2.473(9) . ? Eu1 N1 2.519(10) . ? Eu1 N2 2.561(10) . ? Eu1 H8D 2.7228 . ? O3 Eu1 2.390(8) 3 ? O4 Eu1 2.382(7) 4_554 ? O5 S1 1.457(9) . ? O5 Eu1 2.435(9) 3 ? O6 S1 1.435(9) . ? O7 S1 1.436(9) . ? O8 H8D 0.8500 . ? O8 H8E 0.8500 . ? O9 H9D 0.8500 . ? O9 H9E 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 120.4(11) . . ? O1 C1 C2 122.7(11) . . ? O2 C1 C2 116.9(10) . . ? O1 C1 Eu1 61.7(6) . . ? O2 C1 Eu1 58.6(6) . . ? C2 C1 Eu1 174.7(8) . . ? C8 C2 C3 119.6(11) . . ? C8 C2 C1 120.3(11) . . ? C3 C2 C1 120.1(10) . . ? C2 C3 C4 120.2(11) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C3 C4 C5 120.6(11) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C4 C5 C7 118.7(10) . . ? C4 C5 C6 117.3(10) . . ? C7 C5 C6 124.0(10) . . ? O4 C6 O3 125.7(11) . . ? O4 C6 C5 115.6(9) . . ? O3 C6 C5 118.7(10) . . ? C8 C7 C5 119.4(10) . . ? C8 C7 S1 118.9(9) . . ? C5 C7 S1 121.3(8) . . ? C2 C8 C7 121.4(11) . . ? C2 C8 H8A 119.3 . . ? C7 C8 H8A 119.3 . . ? N1 C9 C10 123.5(14) . . ? N1 C9 H9A 118.2 . . ? C10 C9 H9A 118.2 . . ? C11 C10 C9 118.9(14) . . ? C11 C10 H10A 120.6 . . ? C9 C10 H10A 120.6 . . ? C10 C11 C12 120.7(13) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C19 C12 C11 116.5(13) . . ? C19 C12 C13 119.3(14) . . ? C11 C12 C13 124.1(13) . . ? C14 C13 C12 121.1(13) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C13 C14 C15 121.4(14) . . ? C13 C14 H14A 119.3 . . ? C15 C14 H14A 119.3 . . ? C16 C15 C14 124.2(13) . . ? C16 C15 C20 116.6(11) . . ? C14 C15 C20 119.3(14) . . ? C17 C16 C15 120.4(12) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 119.0(13) . . ? C16 C17 H17A 120.5 . . ? C18 C17 H17A 120.5 . . ? N2 C18 C17 123.6(12) . . ? N2 C18 H18A 118.2 . . ? C17 C18 H18A 118.2 . . ? N1 C19 C12 121.6(13) . . ? N1 C19 C20 119.0(11) . . ? C12 C19 C20 119.4(12) . . ? N2 C20 C19 117.9(11) . . ? N2 C20 C15 122.7(12) . . ? C19 C20 C15 119.4(11) . . ? O8 Eu1 O4 76.4(3) . 4_455 ? O8 Eu1 O3 141.1(3) . 3_445 ? O4 Eu1 O3 142.3(3) 4_455 3_445 ? O8 Eu1 O2 94.1(3) . . ? O4 Eu1 O2 77.3(3) 4_455 . ? O3 Eu1 O2 92.3(3) 3_445 . ? O8 Eu1 O5 145.3(3) . 3_445 ? O4 Eu1 O5 73.9(3) 4_455 3_445 ? O3 Eu1 O5 71.3(3) 3_445 3_445 ? O2 Eu1 O5 96.3(3) . 3_445 ? O8 Eu1 O1 80.8(3) . . ? O4 Eu1 O1 123.1(3) 4_455 . ? O3 Eu1 O1 72.8(3) 3_445 . ? O2 Eu1 O1 53.1(3) . . ? O5 Eu1 O1 130.9(3) 3_445 . ? O8 Eu1 N1 74.7(3) . . ? O4 Eu1 N1 135.9(3) 4_455 . ? O3 Eu1 N1 74.6(3) 3_445 . ? O2 Eu1 N1 137.0(3) . . ? O5 Eu1 N1 116.6(3) 3_445 . ? O1 Eu1 N1 84.0(3) . . ? O8 Eu1 N2 86.6(3) . . ? O4 Eu1 N2 81.4(3) 4_455 . ? O3 Eu1 N2 101.0(3) 3_445 . ? O2 Eu1 N2 157.8(3) . . ? O5 Eu1 N2 71.8(3) 3_445 . ? O1 Eu1 N2 148.1(3) . . ? N1 Eu1 N2 64.5(3) . . ? O8 Eu1 C1 86.8(3) . . ? O4 Eu1 C1 100.8(3) 4_455 . ? O3 Eu1 C1 81.8(3) 3_445 . ? O2 Eu1 C1 27.0(3) . . ? O5 Eu1 C1 115.8(3) 3_445 . ? O1 Eu1 C1 26.1(3) . . ? N1 Eu1 C1 110.0(4) . . ? N2 Eu1 C1 172.5(3) . . ? O8 Eu1 H8D 17.5 . . ? O4 Eu1 H8D 61.6 4_455 . ? O3 Eu1 H8D 155.8 3_445 . ? O2 Eu1 H8D 99.0 . . ? O5 Eu1 H8D 127.8 3_445 . ? O1 Eu1 H8D 97.1 . . ? N1 Eu1 H8D 82.6 . . ? N2 Eu1 H8D 75.8 . . ? C1 Eu1 H8D 98.8 . . ? C9 N1 C19 118.7(11) . . ? C9 N1 Eu1 122.1(9) . . ? C19 N1 Eu1 119.0(8) . . ? C18 N2 C20 117.7(11) . . ? C18 N2 Eu1 122.8(7) . . ? C20 N2 Eu1 118.6(8) . . ? C1 O1 Eu1 92.1(7) . . ? C1 O2 Eu1 94.4(7) . . ? C6 O3 Eu1 145.2(8) . 3 ? C6 O4 Eu1 139.9(8) . 4_554 ? S1 O5 Eu1 143.1(5) . 3 ? Eu1 O8 H8D 105.4 . . ? Eu1 O8 H8E 135.6 . . ? H8D O8 H8E 108.9 . . ? O6 S1 O7 113.3(6) . . ? O6 S1 O5 112.4(6) . . ? O7 S1 O5 110.6(5) . . ? O6 S1 C7 106.4(5) . . ? O7 S1 C7 105.7(5) . . ? O5 S1 C7 108.0(5) . . ? H9D O9 H9E 108.1 . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 1.118 _refine_diff_density_min -0.670 _refine_diff_density_rms 0.122 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 762971' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H13 Eu N2 O8 S' _chemical_formula_weight 593.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2909(3) _cell_length_b 14.5940(3) _cell_length_c 13.9707(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.1410(10) _cell_angle_gamma 90.00 _cell_volume 1886.69(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6484 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 27.62 _exptl_crystal_description cololess _exptl_crystal_colour column _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 3.492 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2246 _exptl_absorpt_correction_T_max 0.7921 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8968 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.62 _reflns_number_total 4361 _reflns_number_gt 4092 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+1.1117P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4361 _refine_ls_number_parameters 296 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0207 _refine_ls_wR_factor_ref 0.0555 _refine_ls_wR_factor_gt 0.0545 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C1 C 0.2578(2) 0.44987(15) 0.36129(16) 0.0198(4) Uani 1 1 d . . . C2 C 0.3824(2) 0.51485(15) 0.36132(15) 0.0183(4) Uani 1 1 d . . . C3 C 0.5235(2) 0.48687(15) 0.38399(16) 0.0189(4) Uani 1 1 d . . . H3 H 0.5440 0.4250 0.3937 0.023 Uiso 1 1 calc R . . C4 C 0.7889(2) 0.52062(15) 0.41617(16) 0.0193(4) Uani 1 1 d . . . C5 C 0.6049(3) 0.64356(15) 0.38122(17) 0.0209(5) Uani 1 1 d . . . H5 H 0.6787 0.6867 0.3895 0.025 Uiso 1 1 calc R . . C6 C 0.4628(2) 0.67130(15) 0.35747(16) 0.0191(4) Uani 1 1 d . . . C7 C 0.3525(2) 0.60732(15) 0.34598(16) 0.0202(4) Uani 1 1 d . . . H7 H 0.2584 0.6262 0.3280 0.024 Uiso 1 1 calc R . . C8 C 0.2381(3) 0.15587(16) 0.4279(2) 0.0292(6) Uani 1 1 d . . . H8 H 0.3060 0.2019 0.4418 0.035 Uiso 1 1 calc R . . C9 C 0.2856(3) 0.06484(19) 0.4293(2) 0.0359(6) Uani 1 1 d . . . H9 H 0.3825 0.0509 0.4450 0.043 Uiso 1 1 calc R . . C10 C 0.0420(3) 0.01856(17) 0.38515(18) 0.0301(6) Uani 1 1 d . . . C11 C 0.0020(3) 0.11161(16) 0.38660(17) 0.0238(5) Uani 1 1 d . . . C12 C -0.1458(3) 0.13697(17) 0.36260(17) 0.0250(5) Uani 1 1 d . . . C13 C -0.0665(4) -0.04939(18) 0.3619(2) 0.0380(7) Uani 1 1 d . . . H13 H -0.0403 -0.1109 0.3621 0.046 Uiso 1 1 calc R . . C14 C -0.2051(4) -0.02623(19) 0.3401(2) 0.0407(7) Uani 1 1 d . . . H14 H -0.2735 -0.0719 0.3260 0.049 Uiso 1 1 calc R . . C15 C -0.2498(3) 0.06812(19) 0.33794(18) 0.0320(6) Uani 1 1 d . . . C16 C -0.3920(3) 0.0960(2) 0.3101(2) 0.0411(7) Uani 1 1 d . . . H16 H -0.4630 0.0525 0.2931 0.049 Uiso 1 1 calc R . . C17 C -0.4257(3) 0.1865(2) 0.3080(2) 0.0415(7) Uani 1 1 d . . . H17 H -0.5194 0.2058 0.2893 0.050 Uiso 1 1 calc R . . C18 C -0.3167(3) 0.2507(2) 0.3345(2) 0.0350(6) Uani 1 1 d . . . H18 H -0.3408 0.3126 0.3328 0.042 Uiso 1 1 calc R . . C24 C 0.1878(3) -0.00286(18) 0.4072(2) 0.0376(6) Uani 1 1 d . . . H24 H 0.2180 -0.0636 0.4069 0.045 Uiso 1 1 calc R . . C30 C 0.6351(2) 0.55085(15) 0.39233(15) 0.0183(4) Uani 1 1 d . . . Eu1 Eu 0.023363(11) 0.346359(7) 0.406228(8) 0.01755(5) Uani 1 1 d . . . N1 N 0.1010(2) 0.17970(14) 0.40780(15) 0.0239(4) Uani 1 1 d . . . N2 N -0.1809(2) 0.22765(14) 0.36192(15) 0.0262(4) Uani 1 1 d . . . O1 O 0.27918(17) 0.36698(11) 0.38428(13) 0.0238(3) Uani 1 1 d . . . O2 O 0.13145(17) 0.48199(11) 0.34422(13) 0.0271(4) Uani 1 1 d . . . O3 O 0.81897(18) 0.43874(12) 0.39859(14) 0.0289(4) Uani 1 1 d . . . O4 O 0.87859(17) 0.57848(12) 0.45142(12) 0.0259(4) Uani 1 1 d . . . O5 O 0.48727(19) 0.81965(13) 0.26043(13) 0.0285(4) Uani 1 1 d . . . O6 O 0.4833(3) 0.83401(13) 0.43119(16) 0.0425(5) Uani 1 1 d . . . O7 O 0.26380(19) 0.79335(12) 0.33313(15) 0.0335(4) Uani 1 1 d . . . O8 O -0.0623(2) 0.28911(16) 0.55846(15) 0.0441(5) Uani 1 1 d D . . S1 S 0.42007(6) 0.78926(4) 0.34604(4) 0.02140(12) Uani 1 1 d . . . H1W H -0.131(4) 0.252(3) 0.587(3) 0.093(13) Uiso 1 1 d D . . H2W H -0.041(5) 0.339(2) 0.601(2) 0.093(13) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0160(10) 0.0187(11) 0.0245(11) -0.0026(8) 0.0007(8) -0.0013(8) C2 0.0145(10) 0.0182(10) 0.0222(10) -0.0026(8) 0.0016(8) -0.0018(8) C3 0.0184(11) 0.0138(10) 0.0242(10) -0.0003(8) 0.0008(8) 0.0016(8) C4 0.0135(10) 0.0198(11) 0.0244(10) -0.0007(8) 0.0003(8) 0.0007(8) C5 0.0189(11) 0.0176(11) 0.0261(11) -0.0002(8) 0.0016(9) -0.0029(8) C6 0.0200(11) 0.0135(10) 0.0239(11) 0.0019(8) 0.0022(9) 0.0016(8) C7 0.0157(10) 0.0185(11) 0.0259(11) 0.0011(8) 0.0002(8) 0.0028(8) C8 0.0273(14) 0.0215(13) 0.0387(15) 0.0010(10) 0.0016(11) 0.0033(9) C9 0.0370(15) 0.0282(14) 0.0435(15) 0.0041(11) 0.0081(12) 0.0131(11) C10 0.0488(16) 0.0161(12) 0.0264(11) -0.0004(9) 0.0087(11) 0.0011(10) C11 0.0333(13) 0.0153(11) 0.0233(11) -0.0014(9) 0.0058(9) -0.0038(9) C12 0.0315(13) 0.0206(11) 0.0236(11) -0.0041(9) 0.0057(10) -0.0087(10) C13 0.065(2) 0.0151(12) 0.0345(14) -0.0018(10) 0.0109(13) -0.0096(12) C14 0.063(2) 0.0253(14) 0.0347(14) -0.0058(11) 0.0090(13) -0.0237(13) C15 0.0391(15) 0.0306(14) 0.0272(12) -0.0055(10) 0.0076(11) -0.0178(12) C16 0.0360(16) 0.0492(18) 0.0384(15) -0.0108(13) 0.0051(12) -0.0258(14) C17 0.0238(13) 0.0537(19) 0.0467(17) -0.0129(15) 0.0016(12) -0.0110(13) C18 0.0228(12) 0.0358(15) 0.0457(16) -0.0092(12) -0.0007(11) -0.0023(10) C24 0.0575(19) 0.0177(12) 0.0390(15) 0.0010(11) 0.0110(13) 0.0106(12) C30 0.0152(10) 0.0167(10) 0.0227(10) -0.0004(8) 0.0006(8) 0.0005(8) Eu1 0.01282(7) 0.01176(7) 0.02773(8) -0.00240(4) -0.00004(5) -0.00045(3) N1 0.0251(10) 0.0156(9) 0.0310(10) -0.0003(8) 0.0025(8) 0.0003(8) N2 0.0208(10) 0.0233(10) 0.0346(11) -0.0055(8) 0.0023(8) -0.0055(8) O1 0.0166(8) 0.0157(7) 0.0388(9) 0.0014(7) 0.0014(7) -0.0010(6) O2 0.0152(8) 0.0205(8) 0.0447(10) 0.0066(7) -0.0023(7) 0.0000(6) O3 0.0187(8) 0.0190(8) 0.0483(11) -0.0062(8) -0.0017(7) 0.0043(6) O4 0.0170(8) 0.0261(9) 0.0341(9) -0.0063(7) -0.0009(7) -0.0035(6) O5 0.0285(9) 0.0247(9) 0.0329(9) 0.0076(7) 0.0052(7) 0.0002(7) O6 0.0632(15) 0.0258(10) 0.0363(11) -0.0089(8) -0.0071(10) 0.0027(9) O7 0.0237(9) 0.0206(9) 0.0574(12) 0.0075(8) 0.0108(8) 0.0054(7) O8 0.0474(13) 0.0490(13) 0.0376(11) -0.0076(10) 0.0130(9) -0.0252(10) S1 0.0226(3) 0.0134(2) 0.0282(3) 0.0013(2) 0.0026(2) 0.0022(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.263(3) . ? C1 O2 1.266(3) . ? C1 C2 1.497(3) . ? C1 Eu1 2.768(2) . ? C2 C3 1.382(3) . ? C2 C7 1.391(3) . ? C3 C30 1.393(3) . ? C4 O4 1.256(3) . ? C4 O3 1.257(3) . ? C4 C30 1.504(3) . ? C5 C30 1.388(3) . ? C5 C6 1.393(3) . ? C6 C7 1.385(3) . ? C6 S1 1.771(2) . ? C8 N1 1.326(3) . ? C8 C9 1.399(3) . ? C9 C24 1.359(4) . ? C10 C24 1.398(4) . ? C10 C11 1.409(3) . ? C10 C13 1.430(4) . ? C11 N1 1.368(3) . ? C11 C12 1.433(4) . ? C12 N2 1.363(3) . ? C12 C15 1.415(3) . ? C13 C14 1.340(5) . ? C14 C15 1.438(4) . ? C15 C16 1.404(4) . ? C16 C17 1.358(5) . ? C17 C18 1.405(4) . ? C18 N2 1.329(3) . ? Eu1 O3 2.3235(16) 1_455 ? Eu1 O5 2.3541(17) 2_545 ? Eu1 O4 2.3798(16) 3_666 ? Eu1 O2 2.4151(17) . ? Eu1 O1 2.4422(16) . ? Eu1 O8 2.482(2) . ? Eu1 N1 2.536(2) . ? Eu1 N2 2.603(2) . ? O3 Eu1 2.3235(16) 1_655 ? O4 Eu1 2.3798(16) 3_666 ? O5 S1 1.4665(18) . ? O5 Eu1 2.3541(17) 2 ? O6 S1 1.436(2) . ? O7 S1 1.4481(19) . ? 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 C1 O2 121.7(2) . . ? O1 C1 C2 120.2(2) . . ? O2 C1 C2 118.0(2) . . ? O1 C1 Eu1 61.89(12) . . ? O2 C1 Eu1 60.67(12) . . ? C2 C1 Eu1 165.94(15) . . ? C3 C2 C7 119.6(2) . . ? C3 C2 C1 122.0(2) . . ? C7 C2 C1 118.09(19) . . ? C2 C3 C30 120.3(2) . . ? O4 C4 O3 124.4(2) . . ? O4 C4 C30 118.3(2) . . ? O3 C4 C30 117.35(19) . . ? C30 C5 C6 119.2(2) . . ? C7 C6 C5 120.5(2) . . ? C7 C6 S1 119.18(17) . . ? C5 C6 S1 120.27(17) . . ? C6 C7 C2 120.1(2) . . ? N1 C8 C9 123.2(3) . . ? C24 C9 C8 118.9(3) . . ? C24 C10 C11 117.7(2) . . ? C24 C10 C13 123.0(3) . . ? C11 C10 C13 119.4(3) . . ? N1 C11 C10 122.0(2) . . ? N1 C11 C12 118.3(2) . . ? C10 C11 C12 119.6(2) . . ? N2 C12 C15 122.0(3) . . ? N2 C12 C11 118.4(2) . . ? C15 C12 C11 119.5(2) . . ? C14 C13 C10 121.3(3) . . ? C13 C14 C15 121.1(3) . . ? C16 C15 C12 117.9(3) . . ? C16 C15 C14 123.1(3) . . ? C12 C15 C14 119.0(3) . . ? C17 C16 C15 119.8(2) . . ? C16 C17 C18 119.0(3) . . ? N2 C18 C17 123.4(3) . . ? C9 C24 C10 120.2(2) . . ? C5 C30 C3 120.2(2) . . ? C5 C30 C4 119.3(2) . . ? C3 C30 C4 120.5(2) . . ? O3 Eu1 O5 95.10(6) 1_455 2_545 ? O3 Eu1 O4 91.20(6) 1_455 3_666 ? O5 Eu1 O4 151.87(6) 2_545 3_666 ? O3 Eu1 O2 82.67(6) 1_455 . ? O5 Eu1 O2 76.28(6) 2_545 . ? O4 Eu1 O2 77.39(6) 3_666 . ? O3 Eu1 O1 136.33(6) 1_455 . ? O5 Eu1 O1 81.45(6) 2_545 . ? O4 Eu1 O1 75.18(6) 3_666 . ? O2 Eu1 O1 54.08(5) . . ? O3 Eu1 O8 84.90(8) 1_455 . ? O5 Eu1 O8 143.48(7) 2_545 . ? O4 Eu1 O8 64.36(6) 3_666 . ? O2 Eu1 O8 139.37(7) . . ? O1 Eu1 O8 122.66(7) . . ? O3 Eu1 N1 141.94(6) 1_455 . ? O5 Eu1 N1 80.59(7) 2_545 . ? O4 Eu1 N1 110.33(6) 3_666 . ? O2 Eu1 N1 131.45(6) . . ? O1 Eu1 N1 80.79(6) . . ? O8 Eu1 N1 77.44(7) . . ? O3 Eu1 N2 78.46(6) 1_455 . ? O5 Eu1 N2 71.91(6) 2_545 . ? O4 Eu1 N2 136.21(6) 3_666 . ? O2 Eu1 N2 141.07(6) . . ? O1 Eu1 N2 138.51(6) . . ? O8 Eu1 N2 72.34(7) . . ? N1 Eu1 N2 64.18(7) . . ? O3 Eu1 C1 109.23(7) 1_455 . ? O5 Eu1 C1 80.22(6) 2_545 . ? O4 Eu1 C1 71.82(6) 3_666 . ? O2 Eu1 C1 27.20(6) . . ? O1 Eu1 C1 27.14(6) . . ? O8 Eu1 C1 134.22(7) . . ? N1 Eu1 C1 107.24(7) . . ? N2 Eu1 C1 151.74(7) . . ? C8 N1 C11 118.0(2) . . ? C8 N1 Eu1 121.36(16) . . ? C11 N1 Eu1 120.61(16) . . ? C18 N2 C12 117.9(2) . . ? C18 N2 Eu1 123.57(18) . . ? C12 N2 Eu1 118.44(16) . . ? C1 O1 Eu1 90.97(13) . . ? C1 O2 Eu1 92.13(13) . . ? C4 O3 Eu1 137.57(15) . 1_655 ? C4 O4 Eu1 145.97(16) . 3_666 ? S1 O5 Eu1 150.86(12) . 2 ? O6 S1 O7 114.55(14) . . ? O6 S1 O5 111.46(13) . . ? O7 S1 O5 112.42(11) . . ? O6 S1 C6 107.21(12) . . ? O7 S1 C6 105.39(11) . . ? O5 S1 C6 105.02(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.809 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.095