# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Sun, Yaguang' _publ_contact_author_email yaguangsun@yahoo.com.cn _publ_section_title ; Solvothermal Synthesis, Crystal Structure, and Properties of Lanthanide-Organic Frameworks Based on Thiophene - 2, 5 - Dicarboxylic acid ; loop_ _publ_author_name Y.Sun B.Jiang T.-f.Cui G.Xiong P.F.Smet F.Ding T.Lv ; K.Van den Eeckhout ; P.Dirk F.Verpoort E.Gao # Attachment '- Crystal data.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 798439' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 La2 N O19.50 S2' _chemical_formula_weight 827.19 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' La La -0.2871 2.4523 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.827(3) _cell_length_b 6.5366(13) _cell_length_c 16.096(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.34(3) _cell_angle_gamma 90.00 _cell_volume 1349.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5963 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 27.83 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.036 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 3.359 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9059 _exptl_absorpt_correction_T_max 0.9359 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11751 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0616 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.83 _reflns_number_total 5963 _reflns_number_gt 5715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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. The highest residual peak is closed to the S1 atom and can not be identified. ; _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^)+(0.0682P)^2^+1.3602P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0175(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(3) _refine_ls_number_reflns 5963 _refine_ls_number_parameters 354 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.059 _refine_ls_shift/su_mean 0.002 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 0.0138(6) -0.0513(13) 0.7927(4) 0.0186(15) Uani 1 1 d U A . C2 C 0.0108(6) -0.0703(15) 0.8846(4) 0.0193(15) Uani 1 1 d . . . C3 C 0.0932(7) -0.0673(15) 0.9380(5) 0.0243(17) Uani 1 1 d . A . H3A H 0.1624 -0.0593 0.9213 0.029 Uiso 1 1 calc R . . C4 C 0.0621(7) -0.0775(16) 1.0207(5) 0.0214(16) Uani 1 1 d . . . H4A H 0.1088 -0.0780 1.0651 0.026 Uiso 1 1 calc R A . C5 C -0.0456(8) -0.0867(16) 1.0308(5) 0.0263(19) Uani 1 1 d . A . C6 C -0.1044(8) -0.0975(14) 1.1075(5) 0.028(2) Uani 1 1 d . . . C7 C 0.3882(9) 0.4168(19) 0.6100(7) 0.039(2) Uani 1 1 d . A . C8 C 0.4702(7) 0.4343(16) 0.5420(7) 0.034(2) Uani 1 1 d . . . C9 C 0.4497(7) 0.4310(19) 0.4609(7) 0.036(2) Uani 1 1 d . B . H9A H 0.3835 0.4214 0.4374 0.043 Uiso 1 1 calc R . . C10 C 0.5385(6) 0.4434(14) 0.4180(6) 0.029(2) Uani 1 1 d . . . H10A H 0.5376 0.4542 0.3604 0.034 Uiso 1 1 calc R B . C11 C 0.6325(6) 0.4396(14) 0.4621(5) 0.0205(16) Uani 1 1 d . B . C12 C 0.7379(6) 0.4510(12) 0.4310(4) 0.0149(14) Uani 1 1 d . . . La1 La 0.01706(3) -0.07066(5) 0.60586(2) 0.01310(13) Uani 1 1 d . . . La2 La 0.21593(4) 0.32218(8) 0.73134(3) 0.01709(13) Uani 1 1 d . . . N1 N 0.0690(5) -0.5205(12) 0.6001(4) 0.0232(16) Uani 1 1 d . . . O1 O -0.0681(5) -0.1011(11) 0.7502(3) 0.0246(15) Uani 1 1 d . . . O2 O 0.0961(5) 0.0092(9) 0.7577(3) 0.0221(12) Uani 1 1 d . . . O3 O -0.2007(5) -0.1273(11) 1.1044(4) 0.0319(17) Uani 1 1 d . . . O4 O -0.0568(5) -0.0847(12) 1.1755(3) 0.0231(13) Uani 1 1 d . . . O5 O 0.2955(6) 0.4329(14) 0.5898(5) 0.0464(19) Uani 1 1 d . . . O6 O 0.4192(5) 0.3868(13) 0.6813(5) 0.046(2) Uani 1 1 d . . . O7 O 0.7543(5) 0.4915(9) 0.3556(4) 0.0237(13) Uani 1 1 d . . . O8 O 0.8132(4) 0.4224(12) 0.4815(3) 0.0208(11) Uani 1 1 d . . . O9 O 0.0274(4) -0.4425(9) 0.5357(3) 0.0187(11) Uani 1 1 d . . . O10 O 0.0850(5) -0.7143(9) 0.6090(4) 0.0222(13) Uani 1 1 d . . . O11 O 0.0992(4) -0.3997(8) 0.6594(3) 0.0135(11) Uani 1 1 d . . . O12 O -0.1371(5) 0.1819(10) 0.6239(4) 0.0278(14) Uani 1 1 d . . . O13 O -0.1567(6) -0.2522(12) 0.5939(5) 0.043(2) Uani 1 1 d . . . O14 O 0.2719(5) 0.6791(10) 0.7719(4) 0.0302(16) Uani 1 1 d . . . O15 O 0.3539(6) 0.1218(15) 0.8150(5) 0.048(2) Uani 1 1 d . . . O16 O 0.8567(6) 0.4358(16) 0.7642(4) 0.0478(19) Uani 1 1 d . . . O18 O 0.559(3) 0.156(4) 0.7683(16) 0.148(17) Uani 0.50 1 d P . . O20 O 0.7048(8) 0.825(3) 0.7267(6) 0.099(5) Uani 1 1 d . . . O19 O 0.6472(14) 0.016(4) 0.9969(12) 0.069(6) Uani 0.50 1 d P . . S1 S -0.10701(18) -0.0840(4) 0.93445(12) 0.0230(4) Uani 1 1 d . A 1 S2 S 0.60509(19) 0.4264(4) 0.56581(14) 0.0307(5) Uani 1 1 d . B 1 O17 O 0.6934(14) 0.362(4) 0.8784(11) 0.067(7) Uani 0.50 1 d P . . O17' O 0.7143(19) 0.166(3) 0.8224(13) 0.075(6) Uani 0.50 1 d P . . O21 O 0.5302(19) 0.664(5) 0.9413(14) 0.090(8) Uani 0.50 1 d P . . 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 0.033(4) 0.011(3) 0.013(3) -0.003(3) 0.010(3) 0.008(3) C2 0.030(4) 0.015(4) 0.013(3) 0.003(4) 0.007(3) 0.005(4) C3 0.041(5) 0.012(4) 0.019(4) 0.000(4) 0.001(3) -0.006(4) C4 0.033(4) 0.015(4) 0.016(3) -0.001(4) -0.005(3) -0.007(4) C5 0.044(5) 0.023(4) 0.012(3) -0.013(4) 0.011(3) -0.016(4) C6 0.056(6) 0.014(4) 0.014(4) -0.004(3) 0.013(4) -0.003(4) C7 0.046(6) 0.027(5) 0.044(6) 0.002(5) 0.001(5) 0.002(5) C8 0.023(4) 0.012(4) 0.067(7) 0.007(5) 0.022(4) -0.002(4) C9 0.018(4) 0.027(5) 0.063(7) -0.006(6) 0.011(4) -0.011(5) C10 0.020(4) 0.008(4) 0.058(6) 0.007(4) -0.010(4) -0.005(4) C11 0.020(4) 0.013(4) 0.028(4) -0.002(4) 0.014(3) 0.003(4) C12 0.017(3) 0.007(3) 0.020(3) -0.001(3) 0.007(3) 0.002(3) La1 0.0204(2) 0.0089(2) 0.01004(19) 0.00001(17) 0.00083(13) 0.00074(18) La2 0.0243(2) 0.0108(2) 0.0161(2) -0.00073(17) -0.00329(15) 0.00057(19) N1 0.018(3) 0.025(4) 0.026(3) 0.004(3) 0.002(3) -0.006(3) O1 0.024(3) 0.040(4) 0.010(2) 0.001(2) 0.005(2) 0.007(3) O2 0.032(3) 0.015(3) 0.019(3) -0.005(2) 0.004(2) -0.006(3) O3 0.036(4) 0.039(5) 0.021(3) -0.003(3) 0.001(3) 0.003(3) O4 0.038(3) 0.023(3) 0.009(2) 0.001(3) 0.009(2) 0.001(3) O5 0.030(4) 0.034(4) 0.075(5) 0.005(5) 0.029(3) 0.006(4) O6 0.025(4) 0.059(6) 0.052(5) -0.010(4) 0.006(3) -0.006(3) O7 0.032(3) 0.018(3) 0.021(3) 0.006(2) 0.002(2) -0.006(2) O8 0.024(3) 0.018(3) 0.021(3) -0.001(3) -0.007(2) 0.002(3) O9 0.022(3) 0.019(3) 0.014(2) 0.000(2) -0.001(2) 0.003(2) O10 0.023(3) 0.012(3) 0.032(3) 0.001(2) -0.005(2) 0.000(2) O11 0.017(3) 0.012(3) 0.012(2) -0.003(2) -0.0002(19) 0.001(2) O12 0.036(4) 0.025(4) 0.022(3) 0.003(3) -0.002(3) 0.013(3) O13 0.032(4) 0.043(5) 0.054(5) -0.025(4) 0.019(3) -0.016(3) O14 0.040(4) 0.014(3) 0.036(4) 0.000(3) -0.015(3) 0.004(3) O15 0.040(4) 0.070(6) 0.033(4) -0.005(4) -0.009(3) 0.013(4) O16 0.059(5) 0.050(5) 0.034(4) -0.008(4) 0.000(3) 0.010(5) O18 0.28(4) 0.067(17) 0.092(19) -0.030(15) -0.09(2) 0.11(2) O20 0.066(7) 0.173(14) 0.059(6) 0.007(8) 0.006(5) -0.048(9) O19 0.045(10) 0.094(17) 0.066(12) -0.002(12) -0.010(9) 0.007(11) S1 0.0364(11) 0.0211(10) 0.0115(8) 0.0000(10) 0.0060(7) -0.0042(11) S2 0.0401(13) 0.0228(11) 0.0293(10) 0.0007(12) 0.0167(9) -0.0007(13) O17 0.056(11) 0.10(2) 0.045(9) 0.016(10) -0.007(8) 0.031(11) O17' 0.100(17) 0.054(13) 0.072(14) 0.021(11) 0.008(12) -0.011(12) O21 0.081(16) 0.12(2) 0.072(14) -0.016(14) -0.030(12) 0.032(15) _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 O2 1.263(10) . ? C1 O1 1.291(10) . ? C1 C2 1.486(9) . ? C2 C3 1.359(12) . ? C2 S1 1.717(8) . ? C3 C4 1.394(11) . ? C3 H3A 0.9300 . ? C4 C5 1.392(12) . ? C4 H4A 0.9300 . ? C5 C6 1.454(10) . ? C5 S1 1.735(9) . ? C6 O3 1.252(12) . ? C6 O4 1.253(11) . ? C6 La2 3.015(8) 2_547 ? C7 O6 1.228(13) . ? C7 O5 1.236(13) . ? C7 C8 1.526(14) . ? C8 C9 1.331(15) . ? C8 S2 1.771(10) . ? C9 C10 1.338(12) . ? C9 H9A 0.9300 . ? C10 C11 1.396(11) . ? C10 H10A 0.9300 . ? C11 C12 1.446(10) . ? C11 S2 1.711(8) . ? C12 O7 1.262(9) . ? C12 O8 1.272(9) . ? La1 O10 2.488(6) 1_565 ? La1 O9 2.491(5) 2_556 ? La1 O13 2.532(7) . ? La1 O11 2.543(5) . ? La1 O1 2.581(5) . ? La1 O12 2.593(6) . ? La1 O8 2.599(6) 2_646 ? La1 O9 2.683(6) . ? La1 O2 2.691(6) . ? La1 O7 3.021(6) 2_646 ? La2 O14 2.526(7) . ? La2 O15 2.576(8) . ? La2 O10 2.591(6) 1_565 ? La2 O2 2.596(6) . ? La2 O7 2.604(6) 2_646 ? La2 O5 2.605(7) . ? La2 O4 2.611(6) 2_557 ? La2 O11 2.621(5) 1_565 ? La2 O3 2.672(6) 2_557 ? La2 O6 2.766(7) . ? La2 N1 3.004(7) 1_565 ? La2 C6 3.015(8) 2_557 ? N1 O9 1.270(9) . ? N1 O10 1.291(10) . ? N1 O11 1.296(9) . ? N1 La2 3.004(7) 1_545 ? O3 La2 2.672(6) 2_547 ? O4 La2 2.611(6) 2_547 ? O7 La2 2.604(6) 2_656 ? O7 La1 3.021(6) 2_656 ? O8 La1 2.599(6) 2_656 ? O9 La1 2.491(5) 2_546 ? O10 La1 2.488(6) 1_545 ? O10 La2 2.591(6) 1_545 ? O11 La2 2.621(5) 1_545 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 121.5(7) . . ? O2 C1 C2 119.8(7) . . ? O1 C1 C2 118.7(7) . . ? C3 C2 C1 127.1(8) . . ? C3 C2 S1 112.9(6) . . ? C1 C2 S1 119.9(6) . . ? C2 C3 C4 112.1(8) . . ? C2 C3 H3A 123.9 . . ? C4 C3 H3A 123.9 . . ? C5 C4 C3 113.8(7) . . ? C5 C4 H4A 123.1 . . ? C3 C4 H4A 123.1 . . ? C4 C5 C6 128.4(8) . . ? C4 C5 S1 109.9(5) . . ? C6 C5 S1 121.6(7) . . ? O3 C6 O4 121.4(8) . . ? O3 C6 C5 119.4(8) . . ? O4 C6 C5 119.1(9) . . ? O3 C6 La2 62.2(4) . 2_547 ? O4 C6 La2 59.4(4) . 2_547 ? C5 C6 La2 172.3(7) . 2_547 ? O6 C7 O5 124.4(11) . . ? O6 C7 C8 117.5(10) . . ? O5 C7 C8 118.1(10) . . ? C9 C8 C7 124.7(9) . . ? C9 C8 S2 113.5(7) . . ? C7 C8 S2 121.3(8) . . ? C8 C9 C10 110.0(9) . . ? C8 C9 H9A 125.0 . . ? C10 C9 H9A 125.0 . . ? C9 C10 C11 118.2(9) . . ? C9 C10 H10A 120.9 . . ? C11 C10 H10A 120.9 . . ? C10 C11 C12 129.1(8) . . ? C10 C11 S2 108.4(6) . . ? C12 C11 S2 122.5(6) . . ? O7 C12 O8 121.0(7) . . ? O7 C12 C11 120.3(7) . . ? O8 C12 C11 118.7(7) . . ? O10 La1 O9 77.4(2) 1_565 2_556 ? O10 La1 O13 138.5(2) 1_565 . ? O9 La1 O13 83.8(2) 2_556 . ? O10 La1 O11 129.83(18) 1_565 . ? O9 La1 O11 133.36(18) 2_556 . ? O13 La1 O11 89.6(2) . . ? O10 La1 O1 101.8(2) 1_565 . ? O9 La1 O1 138.90(19) 2_556 . ? O13 La1 O1 69.8(2) . . ? O11 La1 O1 78.85(19) . . ? O10 La1 O12 70.7(2) 1_565 . ? O9 La1 O12 73.59(19) 2_556 . ? O13 La1 O12 68.6(2) . . ? O11 La1 O12 144.61(19) . . ? O1 La1 O12 67.8(2) . . ? O10 La1 O8 74.5(2) 1_565 2_646 ? O9 La1 O8 72.48(18) 2_556 2_646 ? O13 La1 O8 133.7(2) . 2_646 ? O11 La1 O8 79.7(2) . 2_646 ? O1 La1 O8 147.79(18) . 2_646 ? O12 La1 O8 135.5(2) . 2_646 ? O10 La1 O9 146.97(19) 1_565 . ? O9 La1 O9 86.07(10) 2_556 . ? O13 La1 O9 65.8(2) . . ? O11 La1 O9 49.85(16) . . ? O1 La1 O9 109.3(2) . . ? O12 La1 O9 131.55(19) . . ? O8 La1 O9 73.3(2) 2_646 . ? O10 La1 O2 70.72(19) 1_565 . ? O9 La1 O2 148.0(2) 2_556 . ? O13 La1 O2 119.1(2) . . ? O11 La1 O2 72.74(17) . . ? O1 La1 O2 49.96(19) . . ? O12 La1 O2 93.34(18) . . ? O8 La1 O2 100.51(17) 2_646 . ? O9 La1 O2 122.58(17) . . ? O10 La1 O7 61.99(17) 1_565 2_646 ? O9 La1 O7 111.07(18) 2_556 2_646 ? O13 La1 O7 158.7(2) . 2_646 ? O11 La1 O7 69.16(16) . 2_646 ? O1 La1 O7 103.95(17) . 2_646 ? O12 La1 O7 129.14(19) . 2_646 ? O8 La1 O7 45.44(16) 2_646 2_646 ? O9 La1 O7 99.07(16) . 2_646 ? O2 La1 O7 55.08(17) . 2_646 ? O14 La2 O15 98.1(3) . . ? O14 La2 O10 117.60(19) . 1_565 ? O15 La2 O10 142.2(2) . 1_565 ? O14 La2 O2 148.6(2) . . ? O15 La2 O2 85.4(3) . . ? O10 La2 O2 70.72(19) 1_565 . ? O14 La2 O7 149.7(2) . 2_646 ? O15 La2 O7 75.9(2) . 2_646 ? O10 La2 O7 67.14(19) 1_565 2_646 ? O2 La2 O7 61.46(19) . 2_646 ? O14 La2 O5 81.8(3) . . ? O15 La2 O5 109.1(3) . . ? O10 La2 O5 67.4(2) 1_565 . ? O2 La2 O5 126.7(2) . . ? O7 La2 O5 72.6(2) 2_646 . ? O14 La2 O4 81.9(2) . 2_557 ? O15 La2 O4 110.8(2) . 2_557 ? O10 La2 O4 87.29(19) 1_565 2_557 ? O2 La2 O4 67.9(2) . 2_557 ? O7 La2 O4 128.3(2) 2_646 2_557 ? O5 La2 O4 138.5(2) . 2_557 ? O14 La2 O11 68.54(18) . 1_565 ? O15 La2 O11 166.6(2) . 1_565 ? O10 La2 O11 50.37(17) 1_565 1_565 ? O2 La2 O11 106.36(18) . 1_565 ? O7 La2 O11 115.06(17) 2_646 1_565 ? O5 La2 O11 69.3(2) . 1_565 ? O4 La2 O11 69.25(18) 2_557 1_565 ? O14 La2 O3 69.7(2) . 2_557 ? O15 La2 O3 66.4(2) . 2_557 ? O10 La2 O3 135.4(2) 1_565 2_557 ? O2 La2 O3 83.64(19) . 2_557 ? O7 La2 O3 130.2(2) 2_646 2_557 ? O5 La2 O3 149.6(3) . 2_557 ? O4 La2 O3 48.8(2) 2_557 2_557 ? O11 La2 O3 107.86(19) 1_565 2_557 ? O14 La2 O6 70.5(2) . . ? O15 La2 O6 65.4(3) . . ? O10 La2 O6 113.6(2) 1_565 . ? O2 La2 O6 136.7(2) . . ? O7 La2 O6 80.2(2) 2_646 . ? O5 La2 O6 47.8(2) . . ? O4 La2 O6 150.8(2) 2_557 . ? O11 La2 O6 107.6(2) 1_565 . ? O3 La2 O6 110.1(2) 2_557 . ? O14 La2 N1 92.4(2) . 1_565 ? O15 La2 N1 165.5(2) . 1_565 ? O10 La2 N1 25.3(2) 1_565 1_565 ? O2 La2 N1 90.85(19) . 1_565 ? O7 La2 N1 90.0(2) 2_646 1_565 ? O5 La2 N1 62.4(2) . 1_565 ? O4 La2 N1 80.50(19) 2_557 1_565 ? O11 La2 N1 25.50(18) 1_565 1_565 ? O3 La2 N1 127.2(2) 2_557 1_565 ? O6 La2 N1 109.4(2) . 1_565 ? O14 La2 C6 75.7(2) . 2_557 ? O15 La2 C6 88.1(3) . 2_557 ? O10 La2 C6 111.2(2) 1_565 2_557 ? O2 La2 C6 73.3(2) . 2_557 ? O7 La2 C6 132.7(2) 2_646 2_557 ? O5 La2 C6 153.4(3) . 2_557 ? O4 La2 C6 24.4(2) 2_557 2_557 ? O11 La2 C6 89.2(2) 1_565 2_557 ? O3 La2 C6 24.5(2) 2_557 2_557 ? O6 La2 C6 132.6(3) . 2_557 ? N1 La2 C6 104.3(2) 1_565 2_557 ? O9 N1 O10 123.4(7) . . ? O9 N1 O11 118.6(7) . . ? O10 N1 O11 118.0(7) . . ? O9 N1 La2 166.0(5) . 1_545 ? O10 N1 La2 59.2(4) . 1_545 ? O11 N1 La2 60.5(4) . 1_545 ? C1 O1 La1 96.3(4) . . ? C1 O2 La2 144.8(5) . . ? C1 O2 La1 91.9(5) . . ? La2 O2 La1 103.0(2) . . ? C6 O3 La2 93.3(5) . 2_547 ? C6 O4 La2 96.2(6) . 2_547 ? C7 O5 La2 97.3(7) . . ? C7 O6 La2 89.8(7) . . ? C12 O7 La2 135.8(5) . 2_656 ? C12 O7 La1 86.7(5) . 2_656 ? La2 O7 La1 94.41(18) 2_656 2_656 ? C12 O8 La1 106.7(4) . 2_656 ? N1 O9 La1 134.8(5) . 2_546 ? N1 O9 La1 92.4(4) . . ? La1 O9 La1 132.7(2) 2_546 . ? N1 O10 La1 149.4(5) . 1_545 ? N1 O10 La2 95.5(5) . 1_545 ? La1 O10 La2 109.1(2) 1_545 1_545 ? N1 O11 La1 98.3(4) . . ? N1 O11 La2 94.0(4) . 1_545 ? La1 O11 La2 166.2(2) . 1_545 ? C2 S1 C5 91.2(4) . . ? C11 S2 C8 89.6(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -13.6(15) . . . . ? O1 C1 C2 C3 165.2(9) . . . . ? O2 C1 C2 S1 162.4(7) . . . . ? O1 C1 C2 S1 -18.8(12) . . . . ? C1 C2 C3 C4 176.6(9) . . . . ? S1 C2 C3 C4 0.4(11) . . . . ? C2 C3 C4 C5 -0.5(13) . . . . ? C3 C4 C5 C6 -179.7(9) . . . . ? C3 C4 C5 S1 0.4(12) . . . . ? C4 C5 C6 O3 -172.3(10) . . . . ? S1 C5 C6 O3 7.7(13) . . . . ? C4 C5 C6 O4 5.0(16) . . . . ? S1 C5 C6 O4 -175.1(8) . . . . ? C4 C5 C6 La2 -72(5) . . . 2_547 ? S1 C5 C6 La2 108(5) . . . 2_547 ? O6 C7 C8 C9 167.8(12) . . . . ? O5 C7 C8 C9 -12.0(18) . . . . ? O6 C7 C8 S2 -3.6(16) . . . . ? O5 C7 C8 S2 176.7(9) . . . . ? C7 C8 C9 C10 -178.2(10) . . . . ? S2 C8 C9 C10 -6.2(13) . . . . ? C8 C9 C10 C11 5.3(14) . . . . ? C9 C10 C11 C12 -179.9(10) . . . . ? C9 C10 C11 S2 -1.8(12) . . . . ? C10 C11 C12 O7 8.6(14) . . . . ? S2 C11 C12 O7 -169.2(7) . . . . ? C10 C11 C12 O8 -172.4(9) . . . . ? S2 C11 C12 O8 9.7(12) . . . . ? O2 C1 O1 La1 6.5(9) . . . . ? C2 C1 O1 La1 -172.3(7) . . . . ? O10 La1 O1 C1 -55.4(5) 1_565 . . . ? O9 La1 O1 C1 -139.6(5) 2_556 . . . ? O13 La1 O1 C1 167.1(6) . . . . ? O11 La1 O1 C1 73.4(5) . . . . ? O12 La1 O1 C1 -118.6(5) . . . . ? O8 La1 O1 C1 24.2(8) 2_646 . . . ? O9 La1 O1 C1 113.4(5) . . . . ? O2 La1 O1 C1 -3.4(5) . . . . ? O7 La1 O1 C1 8.4(5) 2_646 . . . ? O1 C1 O2 La2 109.8(9) . . . . ? C2 C1 O2 La2 -71.5(12) . . . . ? O1 C1 O2 La1 -6.2(8) . . . . ? C2 C1 O2 La1 172.6(7) . . . . ? O14 La2 O2 C1 17.4(11) . . . . ? O15 La2 O2 C1 115.5(9) . . . . ? O10 La2 O2 C1 -94.3(9) 1_565 . . . ? O7 La2 O2 C1 -168.1(10) 2_646 . . . ? O5 La2 O2 C1 -134.1(9) . . . . ? O4 La2 O2 C1 0.8(9) 2_557 . . . ? O11 La2 O2 C1 -58.1(9) 1_565 . . . ? O3 La2 O2 C1 48.7(9) 2_557 . . . ? O6 La2 O2 C1 161.4(9) . . . . ? N1 La2 O2 C1 -78.6(9) 1_565 . . . ? C6 La2 O2 C1 26.0(9) 2_557 . . . ? O14 La2 O2 La1 130.1(3) . . . . ? O15 La2 O2 La1 -131.8(2) . . . . ? O10 La2 O2 La1 18.44(19) 1_565 . . . ? O7 La2 O2 La1 -55.4(2) 2_646 . . . ? O5 La2 O2 La1 -21.4(3) . . . . ? O4 La2 O2 La1 113.5(2) 2_557 . . . ? O11 La2 O2 La1 54.6(2) 1_565 . . . ? O3 La2 O2 La1 161.4(2) 2_557 . . . ? O6 La2 O2 La1 -85.9(3) . . . . ? N1 La2 O2 La1 34.1(2) 1_565 . . . ? C6 La2 O2 La1 138.7(3) 2_557 . . . ? O10 La1 O2 C1 128.6(5) 1_565 . . . ? O9 La1 O2 C1 124.3(5) 2_556 . . . ? O13 La1 O2 C1 -6.9(6) . . . . ? O11 La1 O2 C1 -86.4(5) . . . . ? O1 La1 O2 C1 3.4(5) . . . . ? O12 La1 O2 C1 60.5(5) . . . . ? O8 La1 O2 C1 -162.0(5) 2_646 . . . ? O9 La1 O2 C1 -85.2(5) . . . . ? O7 La1 O2 C1 -162.6(6) 2_646 . . . ? O10 La1 O2 La2 -19.24(19) 1_565 . . . ? O9 La1 O2 La2 -23.6(4) 2_556 . . . ? O13 La1 O2 La2 -154.7(2) . . . . ? O11 La1 O2 La2 125.8(2) . . . . ? O1 La1 O2 La2 -144.4(3) . . . . ? O12 La1 O2 La2 -87.4(2) . . . . ? O8 La1 O2 La2 50.1(3) 2_646 . . . ? O9 La1 O2 La2 126.9(2) . . . . ? O7 La1 O2 La2 49.50(19) 2_646 . . . ? O4 C6 O3 La2 -5.7(10) . . . 2_547 ? C5 C6 O3 La2 171.5(8) . . . 2_547 ? O3 C6 O4 La2 5.9(10) . . . 2_547 ? C5 C6 O4 La2 -171.3(8) . . . 2_547 ? O6 C7 O5 La2 -9.2(14) . . . . ? C8 C7 O5 La2 170.5(9) . . . . ? O14 La2 O5 C7 75.7(8) . . . . ? O15 La2 O5 C7 -20.1(8) . . . . ? O10 La2 O5 C7 -159.8(8) 1_565 . . . ? O2 La2 O5 C7 -118.8(7) . . . . ? O7 La2 O5 C7 -87.9(8) 2_646 . . . ? O4 La2 O5 C7 143.4(7) 2_557 . . . ? O11 La2 O5 C7 145.8(8) 1_565 . . . ? O3 La2 O5 C7 55.6(9) 2_557 . . . ? O6 La2 O5 C7 4.5(7) . . . . ? N1 La2 O5 C7 172.8(8) 1_565 . . . ? C6 La2 O5 C7 107.8(9) 2_557 . . . ? O5 C7 O6 La2 8.6(13) . . . . ? C8 C7 O6 La2 -171.2(10) . . . . ? O14 La2 O6 C7 -101.2(8) . . . . ? O15 La2 O6 C7 149.8(8) . . . . ? O10 La2 O6 C7 11.3(8) 1_565 . . . ? O2 La2 O6 C7 97.7(8) . . . . ? O7 La2 O6 C7 70.9(7) 2_646 . . . ? O5 La2 O6 C7 -4.5(7) . . . . ? O4 La2 O6 C7 -121.2(7) 2_557 . . . ? O11 La2 O6 C7 -42.4(8) 1_565 . . . ? O3 La2 O6 C7 -159.7(7) 2_557 . . . ? N1 La2 O6 C7 -15.6(8) 1_565 . . . ? C6 La2 O6 C7 -148.3(7) 2_557 . . . ? O8 C12 O7 La2 -88.3(10) . . . 2_656 ? C11 C12 O7 La2 90.6(10) . . . 2_656 ? O8 C12 O7 La1 4.6(8) . . . 2_656 ? C11 C12 O7 La1 -176.5(7) . . . 2_656 ? O7 C12 O8 La1 -5.5(9) . . . 2_656 ? C11 C12 O8 La1 175.5(6) . . . 2_656 ? O10 N1 O9 La1 -11.5(12) . . . 2_546 ? O11 N1 O9 La1 167.0(5) . . . 2_546 ? La2 N1 O9 La1 85(2) 1_545 . . 2_546 ? O10 N1 O9 La1 172.5(7) . . . . ? O11 N1 O9 La1 -9.0(7) . . . . ? La2 N1 O9 La1 -91(2) 1_545 . . . ? O10 La1 O9 N1 109.1(5) 1_565 . . . ? O9 La1 O9 N1 168.7(5) 2_556 . . . ? O13 La1 O9 N1 -106.4(5) . . . . ? O11 La1 O9 N1 5.3(4) . . . . ? O1 La1 O9 N1 -50.4(5) . . . . ? O12 La1 O9 N1 -127.4(4) . . . . ? O8 La1 O9 N1 95.8(4) 2_646 . . . ? O2 La1 O9 N1 3.8(5) . . . . ? O7 La1 O9 N1 58.0(4) 2_646 . . . ? O10 La1 O9 La1 -67.0(5) 1_565 . . 2_546 ? O9 La1 O9 La1 -7.47(17) 2_556 . . 2_546 ? O13 La1 O9 La1 77.5(4) . . . 2_546 ? O11 La1 O9 La1 -170.9(4) . . . 2_546 ? O1 La1 O9 La1 133.5(3) . . . 2_546 ? O12 La1 O9 La1 56.5(4) . . . 2_546 ? O8 La1 O9 La1 -80.3(3) 2_646 . . 2_546 ? O2 La1 O9 La1 -172.3(3) . . . 2_546 ? O7 La1 O9 La1 -118.2(3) 2_646 . . 2_546 ? O9 N1 O10 La1 -52.2(15) . . . 1_545 ? O11 N1 O10 La1 129.3(9) . . . 1_545 ? La2 N1 O10 La1 144.0(11) 1_545 . . 1_545 ? O9 N1 O10 La2 163.8(6) . . . 1_545 ? O11 N1 O10 La2 -14.7(7) . . . 1_545 ? O9 N1 O11 La1 9.6(7) . . . . ? O10 N1 O11 La1 -171.8(6) . . . . ? La2 N1 O11 La1 173.7(3) 1_545 . . . ? O9 N1 O11 La2 -164.0(6) . . . 1_545 ? O10 N1 O11 La2 14.5(7) . . . 1_545 ? O10 La1 O11 N1 -141.7(4) 1_565 . . . ? O9 La1 O11 N1 -28.3(5) 2_556 . . . ? O13 La1 O11 N1 52.7(4) . . . . ? O1 La1 O11 N1 122.2(4) . . . . ? O12 La1 O11 N1 102.9(5) . . . . ? O8 La1 O11 N1 -82.0(4) 2_646 . . . ? O9 La1 O11 N1 -5.2(4) . . . . ? O2 La1 O11 N1 173.5(4) . . . . ? O7 La1 O11 N1 -128.0(4) 2_646 . . . ? O10 La1 O11 La2 11.0(11) 1_565 . . 1_545 ? O9 La1 O11 La2 124.4(9) 2_556 . . 1_545 ? O13 La1 O11 La2 -154.6(10) . . . 1_545 ? O1 La1 O11 La2 -85.1(10) . . . 1_545 ? O12 La1 O11 La2 -104.4(10) . . . 1_545 ? O8 La1 O11 La2 70.7(10) 2_646 . . 1_545 ? O9 La1 O11 La2 147.4(11) . . . 1_545 ? O2 La1 O11 La2 -33.8(9) . . . 1_545 ? O7 La1 O11 La2 24.6(9) 2_646 . . 1_545 ? C3 C2 S1 C5 -0.2(8) . . . . ? C1 C2 S1 C5 -176.7(8) . . . . ? C4 C5 S1 C2 -0.1(8) . . . . ? C6 C5 S1 C2 179.9(8) . . . . ? C10 C11 S2 C8 -1.5(8) . . . . ? C12 C11 S2 C8 176.7(8) . . . . ? C9 C8 S2 C11 4.6(10) . . . . ? C7 C8 S2 C11 176.8(9) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.83 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 4.275 _refine_diff_density_min -1.401 _refine_diff_density_rms 0.212 data_2 _database_code_depnum_ccdc_archive 'CCDC 798440' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 N Nd O8 S' _chemical_formula_weight 394.40 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' Nd Nd -0.1943 3.0179 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 9.8814(16) _cell_length_b 14.1582(9) _cell_length_c 7.885 _cell_angle_alpha 90.00 _cell_angle_beta 104.12 _cell_angle_gamma 90.00 _cell_volume 1069.86(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2548 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 27.87 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 5.078 _exptl_absorpt_correction_type muiti-scan _exptl_absorpt_correction_T_min 0.3111 _exptl_absorpt_correction_T_max 0.4299 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8595 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.17 _reflns_number_total 2548 _reflns_number_gt 2122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0628P)^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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0234(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2548 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0.047 _refine_ls_shift/su_mean 0.002 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 0.7810(2) 0.39397(13) 0.8184(3) 0.0194(5) Uani 1 1 d . . . C2 C 0.66474(19) 0.33293(14) 0.7271(3) 0.0166(5) Uani 1 1 d . . . C3 C 0.6551(2) 0.23824(15) 0.7435(3) 0.0239(6) Uani 1 1 d . . . H3 H 0.7258 0.2011 0.8109 0.029 Uiso 1 1 calc R . . C4 C 0.5287(2) 0.20262(15) 0.6493(3) 0.0227(6) Uani 1 1 d . . . H4 H 0.5047 0.1391 0.6485 0.027 Uiso 1 1 calc R . . C5 C 0.44357(19) 0.26983(14) 0.5583(3) 0.0173(5) Uani 1 1 d . . . C6 C 0.3037(2) 0.25940(14) 0.4404(3) 0.0156(5) Uani 1 1 d . . . N1 N 0.89432(19) 0.46882(14) 1.2708(3) 0.0284(5) Uani 1 1 d . . . Nd1 Nd 1.096180(9) 0.387331(6) 1.103843(12) 0.00758(3) Uani 1 1 d . . . O1 O 0.88152(16) 0.35382(11) 0.9153(2) 0.0277(5) Uani 1 1 d . . . O2 O 0.76705(15) 0.48120(10) 0.7917(2) 0.0241(4) Uani 1 1 d . . . O3 O 0.24201(14) 0.18211(10) 0.44071(19) 0.0188(4) Uani 1 1 d . . . O4 O 0.25617(14) 0.32851(10) 0.34758(19) 0.0185(4) Uani 1 1 d . . . O5 O 0.96325(16) 0.39765(9) 1.3345(2) 0.0204(4) Uani 1 1 d . . . O6 O 0.92917(14) 0.51296(10) 1.14690(19) 0.0210(4) Uani 1 1 d . . . O7 O 0.7724(2) 0.50197(16) 1.3425(3) 0.0600(8) Uani 1 1 d . . . O8 O 1.04436(16) 0.22382(10) 1.12319(19) 0.0217(4) Uani 1 1 d . . . H8A H 0.9802 0.2066 1.1714 0.026 Uiso 1 1 d R . . H8B H 1.0903 0.1827 1.0820 0.026 Uiso 1 1 d R . . S1 S 0.51880(5) 0.37918(3) 0.59147(7) 0.01761(13) 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 C1 0.0164(9) 0.0140(8) 0.0233(10) 0.0000(8) -0.0035(8) -0.0014(7) C2 0.0123(8) 0.0133(8) 0.0218(9) 0.0028(8) -0.0005(7) -0.0007(7) C3 0.0225(10) 0.0149(9) 0.0303(11) 0.0016(9) -0.0017(9) 0.0008(8) C4 0.0199(9) 0.0148(9) 0.0310(11) 0.0030(8) 0.0014(9) -0.0018(8) C5 0.0147(8) 0.0157(8) 0.0194(9) 0.0006(8) 0.0001(7) -0.0021(7) C6 0.0160(8) 0.0141(8) 0.0163(9) -0.0013(7) 0.0032(7) 0.0020(7) N1 0.0274(9) 0.0236(9) 0.0327(10) -0.0039(8) 0.0043(8) -0.0039(8) Nd1 0.00618(5) 0.00535(5) 0.00963(5) 0.00024(3) -0.00110(4) 0.00039(3) O1 0.0204(7) 0.0176(7) 0.0363(9) 0.0023(7) -0.0101(7) -0.0013(6) O2 0.0220(7) 0.0151(6) 0.0278(8) 0.0033(6) -0.0082(6) 0.0007(6) O3 0.0154(6) 0.0148(6) 0.0238(7) -0.0001(6) 0.0001(5) -0.0041(5) O4 0.0176(6) 0.0129(6) 0.0210(7) 0.0029(6) -0.0028(5) -0.0014(5) O5 0.0246(7) 0.0161(7) 0.0200(7) 0.0055(6) 0.0044(6) 0.0036(5) O6 0.0240(7) 0.0221(7) 0.0193(7) 0.0081(6) 0.0100(6) 0.0058(6) O7 0.0592(11) 0.0503(13) 0.0788(16) -0.0025(12) 0.0325(11) 0.0098(11) O8 0.0267(7) 0.0133(6) 0.0244(7) 0.0014(6) 0.0053(6) -0.0027(6) S1 0.0143(2) 0.0123(2) 0.0227(3) 0.00167(18) -0.0024(2) -0.00036(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 C1 O1 1.234(2) . ? C1 O2 1.255(2) . ? C1 C2 1.477(3) . ? C2 C3 1.352(3) . ? C2 S1 1.7029(18) . ? C3 C4 1.383(3) . ? C3 H3 0.9300 . ? C4 C5 1.354(3) . ? C4 H4 0.9300 . ? C5 C6 1.473(2) . ? C5 S1 1.710(2) . ? C6 O4 1.243(2) . ? C6 O3 1.253(2) . ? N1 O5 1.251(2) . ? N1 O6 1.276(3) . ? N1 O7 1.525(3) . ? Nd1 O1 2.3230(14) . ? Nd1 O4 2.3247(13) 1_656 ? Nd1 O2 2.3294(14) 3_767 ? Nd1 O3 2.3669(16) 4_666 ? Nd1 O8 2.3839(14) . ? Nd1 O6 2.3923(15) 3_767 ? Nd1 O5 2.4938(18) . ? Nd1 O6 2.5052(15) . ? Nd1 Nd1 3.8671(3) 3_767 ? O2 Nd1 2.3294(14) 3_767 ? O3 Nd1 2.3669(16) 4_465 ? O4 Nd1 2.3247(13) 1_454 ? O6 Nd1 2.3923(15) 3_767 ? O8 H8A 0.8500 . ? O8 H8B 0.8499 . ? 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 126.59(19) . . ? O1 C1 C2 116.43(17) . . ? O2 C1 C2 116.97(18) . . ? C3 C2 C1 126.72(17) . . ? C3 C2 S1 111.89(14) . . ? C1 C2 S1 121.33(14) . . ? C2 C3 C4 112.66(18) . . ? C2 C3 H3 123.7 . . ? C4 C3 H3 123.7 . . ? C5 C4 C3 113.03(19) . . ? C5 C4 H4 123.5 . . ? C3 C4 H4 123.5 . . ? C4 C5 C6 129.05(18) . . ? C4 C5 S1 111.39(14) . . ? C6 C5 S1 119.56(14) . . ? O4 C6 O3 125.05(17) . . ? O4 C6 C5 117.02(17) . . ? O3 C6 C5 117.93(17) . . ? O5 N1 O6 118.7(2) . . ? O5 N1 O7 120.1(2) . . ? O6 N1 O7 121.25(17) . . ? O1 Nd1 O4 141.87(5) . 1_656 ? O1 Nd1 O2 138.58(5) . 3_767 ? O4 Nd1 O2 77.00(5) 1_656 3_767 ? O1 Nd1 O3 98.58(5) . 4_666 ? O4 Nd1 O3 85.36(5) 1_656 4_666 ? O2 Nd1 O3 98.42(5) 3_767 4_666 ? O1 Nd1 O8 70.47(5) . . ? O4 Nd1 O8 73.30(5) 1_656 . ? O2 Nd1 O8 150.29(5) 3_767 . ? O3 Nd1 O8 78.47(5) 4_666 . ? O1 Nd1 O6 72.32(5) . 3_767 ? O4 Nd1 O6 143.87(5) 1_656 3_767 ? O2 Nd1 O6 75.84(5) 3_767 3_767 ? O3 Nd1 O6 75.57(5) 4_666 3_767 ? O8 Nd1 O6 130.17(5) . 3_767 ? O1 Nd1 O5 85.27(6) . . ? O4 Nd1 O5 77.94(5) 1_656 . ? O2 Nd1 O5 93.37(5) 3_767 . ? O3 Nd1 O5 156.85(5) 4_666 . ? O8 Nd1 O5 81.41(5) . . ? O6 Nd1 O5 126.91(5) 3_767 . ? O1 Nd1 O6 72.72(5) . . ? O4 Nd1 O6 118.68(5) 1_656 . ? O2 Nd1 O6 74.30(5) 3_767 . ? O3 Nd1 O6 151.29(5) 4_666 . ? O8 Nd1 O6 121.46(5) . . ? O6 Nd1 O6 75.73(6) 3_767 . ? O5 Nd1 O6 51.54(5) . . ? O1 Nd1 Nd1 67.65(4) . 3_767 ? O4 Nd1 Nd1 144.15(3) 1_656 3_767 ? O2 Nd1 Nd1 70.93(3) 3_767 3_767 ? O3 Nd1 Nd1 114.46(3) 4_666 3_767 ? O8 Nd1 Nd1 137.49(3) . 3_767 ? O6 Nd1 Nd1 38.89(4) 3_767 3_767 ? O5 Nd1 Nd1 88.20(3) . 3_767 ? O6 Nd1 Nd1 36.84(4) . 3_767 ? C1 O1 Nd1 140.66(14) . . ? C1 O2 Nd1 134.16(13) . 3_767 ? C6 O3 Nd1 136.47(14) . 4_465 ? C6 O4 Nd1 148.39(12) . 1_454 ? N1 O5 Nd1 94.96(14) . . ? N1 O6 Nd1 158.20(12) . 3_767 ? N1 O6 Nd1 93.77(12) . . ? Nd1 O6 Nd1 104.27(6) 3_767 . ? Nd1 O8 H8A 120.1 . . ? Nd1 O8 H8B 119.9 . . ? H8A O8 H8B 120.0 . . ? C2 S1 C5 91.02(9) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.17 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 2.166 _refine_diff_density_min -1.242 _refine_diff_density_rms 0.354 data_3 _database_code_depnum_ccdc_archive 'CCDC 798441' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H4 O8 S Sm' _chemical_formula_weight 398.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 9.946(4) _cell_length_b 14.420(5) _cell_length_c 7.675(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.709(6) _cell_angle_gamma 90.00 _cell_volume 1073.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2551 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 27.90 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 2.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 5.690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3957 _exptl_absorpt_correction_T_max 0.3957 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method 0 _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9686 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.90 _reflns_number_total 2551 _reflns_number_gt 2172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XSCANS' _computing_publication_material 'Bruker XSCANS' _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^)+(0.0400P)^2^+0.3014P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2551 _refine_ls_number_parameters 154 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.150 _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 0.2225(4) 0.1069(2) 0.1741(5) 0.0088(7) Uani 1 1 d . . . C2 C 0.3353(3) 0.1681(2) 0.2657(5) 0.0077(7) Uani 1 1 d . . . C3 C 0.3427(4) 0.2625(2) 0.2530(5) 0.0121(8) Uani 1 1 d . . . H3 H 0.2724 0.2991 0.1874 0.015 Uiso 1 1 calc R . . C4 C 0.4683(4) 0.2979(2) 0.3503(5) 0.0110(7) Uani 1 1 d . . . H4 H 0.4910 0.3606 0.3545 0.013 Uiso 1 1 calc R . . C5 C 0.5538(3) 0.2306(2) 0.4383(5) 0.0086(7) Uani 1 1 d . . . C6 C 0.6919(3) 0.2405(2) 0.5577(5) 0.0070(7) Uani 1 1 d . . . N1 N 0.1036(4) 0.0298(2) -0.2789(5) 0.0205(8) Uani 1 1 d . . . O1 O 0.1210(2) 0.14597(18) 0.0733(4) 0.0123(6) Uani 1 1 d . . . O2 O 0.2364(3) 0.02045(15) 0.2007(4) 0.0112(5) Uani 1 1 d . . . O3 O 0.7528(2) 0.31878(16) 0.5612(3) 0.0080(5) Uani 1 1 d . . . O4 O 0.7413(2) 0.17170(16) 0.6473(3) 0.0092(5) Uani 1 1 d . . . O6 O 0.0657(2) -0.01557(16) -0.1553(3) 0.0089(5) Uani 1 1 d . . . O5 O 0.0354(3) 0.10070(15) -0.3433(4) 0.0103(5) Uani 1 1 d . . . O7 O 0.2287(4) -0.0011(3) -0.3445(6) 0.0491(11) Uani 1 1 d . . . O8 O -0.0493(3) 0.27579(16) -0.1266(4) 0.0110(5) Uani 1 1 d . . . H8A H -0.0102 0.3089 -0.0379 0.017 Uiso 1 1 d R . . H8B H -0.1053 0.3037 -0.2095 0.017 Uiso 1 1 d R . . S1 S 0.48090(9) 0.12207(6) 0.40154(13) 0.00852(19) Uani 1 1 d . . . Sm1 Sm -0.098171(17) 0.112041(11) -0.10537(2) 0.00512(8) 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 C1 0.0077(17) 0.0078(17) 0.010(2) -0.0004(14) 0.0007(14) -0.0007(12) C2 0.0076(16) 0.0088(16) 0.0063(18) 0.0021(14) 0.0006(13) 0.0011(13) C3 0.0110(18) 0.0078(16) 0.015(2) 0.0019(15) -0.0018(15) 0.0008(14) C4 0.0100(17) 0.0067(16) 0.015(2) 0.0013(14) 0.0002(14) -0.0032(13) C5 0.0078(16) 0.0097(16) 0.0084(19) -0.0003(14) 0.0021(13) -0.0022(13) C6 0.0081(16) 0.0083(16) 0.0055(18) -0.0018(14) 0.0037(13) 0.0012(13) N1 0.0214(19) 0.0213(18) 0.018(2) -0.0045(15) 0.0032(15) -0.0047(15) O1 0.0096(13) 0.0097(12) 0.0148(15) 0.0006(11) -0.0038(11) -0.0017(10) O2 0.0098(12) 0.0063(11) 0.0146(15) 0.0020(10) -0.0038(10) -0.0005(10) O3 0.0069(12) 0.0072(11) 0.0092(13) -0.0008(10) 0.0005(9) -0.0030(9) O4 0.0089(12) 0.0062(11) 0.0107(14) 0.0014(10) -0.0018(10) -0.0002(10) O6 0.0127(13) 0.0090(12) 0.0062(14) 0.0030(10) 0.0046(10) 0.0019(10) O5 0.0135(13) 0.0063(12) 0.0113(15) 0.0040(10) 0.0028(11) 0.0052(9) O7 0.041(2) 0.051(2) 0.061(3) -0.003(2) 0.023(2) 0.0049(18) O8 0.0144(13) 0.0066(12) 0.0093(14) 0.0007(10) -0.0035(10) 0.0000(10) S1 0.0064(4) 0.0062(4) 0.0111(5) 0.0011(3) -0.0022(3) -0.0004(3) Sm1 0.00479(11) 0.00416(11) 0.00582(12) 0.00025(6) -0.00009(7) 0.00038(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 1.261(4) . ? C1 O2 1.266(4) . ? C1 C2 1.478(5) . ? C2 C3 1.368(5) . ? C2 S1 1.721(4) . ? C3 C4 1.403(5) . ? C3 H3 0.9300 . ? C4 C5 1.367(5) . ? C4 H4 0.9300 . ? C5 C6 1.481(5) . ? C5 S1 1.722(3) . ? C6 O4 1.245(4) . ? C6 O3 1.278(4) . ? N1 O5 1.265(4) . ? N1 O6 1.276(4) . ? N1 O7 1.509(5) . ? O1 Sm1 2.357(2) . ? O2 Sm1 2.373(2) 3 ? O3 Sm1 2.379(2) 4_666 ? O4 Sm1 2.358(3) 1_656 ? O6 Sm1 2.400(3) 3 ? O6 Sm1 2.543(2) . ? O5 Sm1 2.489(3) . ? O8 Sm1 2.424(2) . ? O8 H8A 0.8517 . ? O8 H8B 0.8494 . ? Sm1 O4 2.358(3) 1_454 ? Sm1 O2 2.373(2) 3 ? Sm1 O3 2.379(2) 4_465 ? Sm1 O6 2.400(3) 3 ? Sm1 Sm1 3.9346(10) 3 ? 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 125.7(3) . . ? O1 C1 C2 116.5(3) . . ? O2 C1 C2 117.8(3) . . ? C3 C2 C1 127.4(3) . . ? C3 C2 S1 112.1(3) . . ? C1 C2 S1 120.5(2) . . ? C2 C3 C4 112.3(3) . . ? C2 C3 H3 123.9 . . ? C4 C3 H3 123.9 . . ? C5 C4 C3 112.9(3) . . ? C5 C4 H4 123.5 . . ? C3 C4 H4 123.5 . . ? C4 C5 C6 129.0(3) . . ? C4 C5 S1 111.8(3) . . ? C6 C5 S1 119.3(3) . . ? O4 C6 O3 124.3(3) . . ? O4 C6 C5 117.7(3) . . ? O3 C6 C5 118.0(3) . . ? O5 N1 O6 119.0(3) . . ? O5 N1 O7 121.3(3) . . ? O6 N1 O7 119.7(3) . . ? C1 O1 Sm1 141.0(2) . . ? C1 O2 Sm1 135.0(2) . 3 ? C6 O3 Sm1 135.0(2) . 4_666 ? C6 O4 Sm1 148.3(2) . 1_656 ? N1 O6 Sm1 155.5(2) . 3 ? N1 O6 Sm1 92.55(19) . . ? Sm1 O6 Sm1 105.47(9) 3 . ? N1 O5 Sm1 95.3(2) . . ? Sm1 O8 H8A 123.7 . . ? Sm1 O8 H8B 113.8 . . ? H8A O8 H8B 116.2 . . ? C2 S1 C5 90.93(17) . . ? O1 Sm1 O4 140.21(9) . 1_454 ? O1 Sm1 O2 138.18(8) . 3 ? O4 Sm1 O2 78.56(8) 1_454 3 ? O1 Sm1 O3 101.90(9) . 4_465 ? O4 Sm1 O3 83.57(9) 1_454 4_465 ? O2 Sm1 O3 96.66(9) 3 4_465 ? O1 Sm1 O6 72.41(9) . 3 ? O4 Sm1 O6 145.67(8) 1_454 3 ? O2 Sm1 O6 75.70(9) 3 3 ? O3 Sm1 O6 77.32(8) 4_465 3 ? O1 Sm1 O8 70.33(9) . . ? O4 Sm1 O8 72.58(8) 1_454 . ? O2 Sm1 O8 151.01(8) 3 . ? O3 Sm1 O8 77.62(8) 4_465 . ? O6 Sm1 O8 128.96(9) 3 . ? O1 Sm1 O5 82.31(10) . . ? O4 Sm1 O5 79.00(9) 1_454 . ? O2 Sm1 O5 95.01(9) 3 . ? O3 Sm1 O5 156.64(8) 4_465 . ? O6 Sm1 O5 125.33(8) 3 . ? O8 Sm1 O5 82.38(8) . . ? O1 Sm1 O6 72.33(9) . . ? O4 Sm1 O6 119.05(9) 1_454 . ? O2 Sm1 O6 73.63(8) 3 . ? O3 Sm1 O6 151.69(8) 4_465 . ? O6 Sm1 O6 74.53(9) 3 . ? O8 Sm1 O6 123.38(8) . . ? O5 Sm1 O6 51.57(8) . . ? O1 Sm1 Sm1 67.63(6) . 3 ? O4 Sm1 Sm1 144.84(6) 1_454 3 ? O2 Sm1 Sm1 70.56(6) 3 3 ? O3 Sm1 Sm1 115.79(6) 4_465 3 ? O6 Sm1 Sm1 38.52(6) 3 3 ? O8 Sm1 Sm1 137.65(6) . 3 ? O5 Sm1 Sm1 87.19(6) . 3 ? O6 Sm1 Sm1 36.00(6) . 3 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -0.4(6) . . . . ? O2 C1 C2 C3 178.6(4) . . . . ? O1 C1 C2 S1 -178.2(3) . . . . ? O2 C1 C2 S1 0.7(5) . . . . ? C1 C2 C3 C4 -176.5(4) . . . . ? S1 C2 C3 C4 1.5(4) . . . . ? C2 C3 C4 C5 -1.1(5) . . . . ? C3 C4 C5 C6 -178.1(4) . . . . ? C3 C4 C5 S1 0.3(4) . . . . ? C4 C5 C6 O4 168.0(4) . . . . ? S1 C5 C6 O4 -10.2(5) . . . . ? C4 C5 C6 O3 -12.4(6) . . . . ? S1 C5 C6 O3 169.3(3) . . . . ? O2 C1 O1 Sm1 5.3(7) . . . . ? C2 C1 O1 Sm1 -175.8(3) . . . . ? O1 C1 O2 Sm1 -2.9(6) . . . 3 ? C2 C1 O2 Sm1 178.2(2) . . . 3 ? O4 C6 O3 Sm1 91.5(4) . . . 4_666 ? C5 C6 O3 Sm1 -88.1(4) . . . 4_666 ? O3 C6 O4 Sm1 19.8(7) . . . 1_656 ? C5 C6 O4 Sm1 -160.7(3) . . . 1_656 ? O5 N1 O6 Sm1 -150.3(4) . . . 3 ? O7 N1 O6 Sm1 29.2(7) . . . 3 ? O5 N1 O6 Sm1 -12.5(3) . . . . ? O7 N1 O6 Sm1 167.1(3) . . . . ? O6 N1 O5 Sm1 12.8(3) . . . . ? O7 N1 O5 Sm1 -166.8(3) . . . . ? C3 C2 S1 C5 -1.1(3) . . . . ? C1 C2 S1 C5 177.1(3) . . . . ? C4 C5 S1 C2 0.4(3) . . . . ? C6 C5 S1 C2 179.0(3) . . . . ? C1 O1 Sm1 O4 -156.1(4) . . . 1_454 ? C1 O1 Sm1 O2 -4.8(5) . . . 3 ? C1 O1 Sm1 O3 109.6(4) . . . 4_465 ? C1 O1 Sm1 O6 37.2(4) . . . 3 ? C1 O1 Sm1 O8 -178.3(4) . . . . ? C1 O1 Sm1 O5 -93.7(4) . . . . ? C1 O1 Sm1 O6 -41.7(4) . . . . ? C1 O1 Sm1 Sm1 -3.6(4) . . . 3 ? N1 O5 Sm1 O1 66.4(2) . . . . ? N1 O5 Sm1 O4 -148.9(2) . . . 1_454 ? N1 O5 Sm1 O2 -71.6(2) . . . 3 ? N1 O5 Sm1 O3 168.6(2) . . . 4_465 ? N1 O5 Sm1 O6 4.4(2) . . . 3 ? N1 O5 Sm1 O8 137.5(2) . . . . ? N1 O5 Sm1 O6 -7.11(19) . . . . ? N1 O5 Sm1 Sm1 -1.4(2) . . . 3 ? N1 O6 Sm1 O1 -87.2(2) . . . . ? Sm1 O6 Sm1 O1 76.06(10) 3 . . . ? N1 O6 Sm1 O4 51.0(2) . . . 1_454 ? Sm1 O6 Sm1 O4 -145.73(9) 3 . . 1_454 ? N1 O6 Sm1 O2 117.5(2) . . . 3 ? Sm1 O6 Sm1 O2 -79.29(10) 3 . . 3 ? N1 O6 Sm1 O3 -169.4(2) . . . 4_465 ? Sm1 O6 Sm1 O3 -6.2(2) 3 . . 4_465 ? N1 O6 Sm1 O6 -163.2(2) . . . 3 ? Sm1 O6 Sm1 O6 0.0 3 . . 3 ? N1 O6 Sm1 O8 -36.4(2) . . . . ? Sm1 O6 Sm1 O8 126.79(10) 3 . . . ? N1 O6 Sm1 O5 7.03(19) . . . . ? Sm1 O6 Sm1 O5 170.27(14) 3 . . . ? N1 O6 Sm1 Sm1 -163.2(2) . . . 3 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.315 _refine_diff_density_min -1.227 _refine_diff_density_rms 0.186 data_4 _database_code_depnum_ccdc_archive 'CCDC 798442' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Eu N O8 S' _chemical_formula_weight 402.12 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' Eu Eu -0.1578 3.6682 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 9.8814(16) _cell_length_b 14.1582(9) _cell_length_c 7.885 _cell_angle_alpha 90.00 _cell_angle_beta 104.12 _cell_angle_gamma 90.00 _cell_volume 1069.86(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2093 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 26 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 6.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2624 _exptl_absorpt_correction_T_max 0.3756 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8175 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2093 _reflns_number_gt 1955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _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^)+(0.0501P)^2^+9.9004P] 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 SHELXL _refine_ls_extinction_coef 0.0094(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2093 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7789(7) 0.3940(4) 0.8205(8) 0.0123(13) Uani 1 1 d . . . C2 C 0.6645(6) 0.3329(4) 0.7295(8) 0.0102(11) Uani 1 1 d . . . C3 C 0.6565(7) 0.2382(5) 0.7440(9) 0.0170(13) Uani 1 1 d . . . H3 H 0.7278 0.2011 0.8100 0.020 Uiso 1 1 calc R . . C4 C 0.5292(6) 0.2022(4) 0.6491(9) 0.0158(13) Uani 1 1 d . . . H4 H 0.5050 0.1387 0.6477 0.019 Uiso 1 1 calc R . . C5 C 0.4444(6) 0.2700(4) 0.5591(8) 0.0101(11) Uani 1 1 d . . . C6 C 0.3053(6) 0.2595(4) 0.4414(7) 0.0079(11) Uani 1 1 d . . . Eu1 Eu 1.09697(3) 0.387515(18) 1.10424(3) 0.00567(16) Uani 1 1 d . . . N1 N 0.8849(6) 0.4712(4) 1.2787(8) 0.0256(14) Uani 1 1 d D . . O1 O 0.8812(5) 0.3543(3) 0.9190(6) 0.0182(10) Uani 1 1 d . . . O2 O 0.7656(4) 0.4804(3) 0.7940(6) 0.0158(9) Uani 1 1 d . . . O3 O 0.2438(4) 0.1821(3) 0.4404(5) 0.0103(8) Uani 1 1 d . . . O4 O 0.2573(4) 0.3286(3) 0.3496(5) 0.0120(9) Uani 1 1 d . . . O6 O 0.9307(4) 0.5134(3) 1.1490(5) 0.0127(9) Uani 1 1 d . . . O5 O 0.9634(5) 0.3983(3) 1.3374(6) 0.0126(9) Uani 1 1 d . . . O7 O 0.7836(7) 0.4990(5) 1.3351(10) 0.0550(19) Uani 1 1 d D . . O8 O 1.0460(5) 0.2233(3) 1.1234(6) 0.0140(9) Uani 1 1 d . . . H8A H 0.9819 0.2061 1.1716 0.017 Uiso 1 1 d R . . H8B H 1.0920 0.1822 1.0823 0.017 Uiso 1 1 d R . . S1 S 0.51914(15) 0.37871(10) 0.5935(2) 0.0108(3) 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 C1 0.008(3) 0.012(3) 0.012(3) 0.000(2) -0.007(2) -0.001(2) C2 0.006(3) 0.008(3) 0.015(3) 0.002(2) 0.000(2) -0.001(2) C3 0.012(3) 0.014(3) 0.022(3) 0.004(2) -0.002(2) 0.002(2) C4 0.012(3) 0.009(3) 0.023(3) 0.002(2) -0.003(2) -0.002(2) C5 0.009(3) 0.008(3) 0.012(3) 0.001(2) 0.001(2) -0.003(2) C6 0.006(3) 0.009(3) 0.008(3) -0.001(2) 0.002(2) 0.000(2) Eu1 0.0044(2) 0.0033(2) 0.0079(2) 0.00030(9) -0.00133(12) 0.00044(9) N1 0.028(3) 0.018(3) 0.028(3) -0.005(2) 0.000(3) -0.005(3) O1 0.012(2) 0.009(2) 0.026(3) 0.0033(18) -0.0091(18) 0.0002(18) O2 0.010(2) 0.007(2) 0.024(2) 0.0035(17) -0.0079(17) -0.0002(16) O3 0.0064(19) 0.008(2) 0.015(2) 0.0028(16) -0.0004(15) -0.0038(15) O4 0.009(2) 0.009(2) 0.014(2) 0.0040(16) -0.0057(15) -0.0006(16) O6 0.017(2) 0.010(2) 0.012(2) 0.0053(16) 0.0055(17) 0.0044(17) O5 0.015(2) 0.007(2) 0.015(2) 0.0052(16) 0.0022(18) 0.0058(16) O7 0.051(4) 0.046(4) 0.069(5) -0.003(4) 0.018(4) 0.000(3) O8 0.018(2) 0.006(2) 0.017(2) 0.0002(16) 0.0014(17) -0.0045(17) S1 0.0080(7) 0.0059(7) 0.0151(8) 0.0019(5) -0.0038(6) -0.0006(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 C1 O2 1.242(7) . ? C1 O1 1.249(8) . ? C1 C2 1.465(8) . ? C2 C3 1.349(9) . ? C2 S1 1.698(6) . ? C3 C4 1.394(9) . ? C3 H3 0.9300 . ? C4 C5 1.355(8) . ? C4 H4 0.9300 . ? C5 C6 1.466(8) . ? C5 S1 1.700(6) . ? C6 O4 1.241(7) . ? C6 O3 1.251(7) . ? Eu1 O1 2.320(4) . ? Eu1 O2 2.335(4) 3_767 ? Eu1 O4 2.335(4) 1_656 ? Eu1 O3 2.379(4) 4_666 ? Eu1 O8 2.391(4) . ? Eu1 O6 2.401(4) 3_767 ? Eu1 O6 2.506(4) . ? Eu1 O5 2.516(5) . ? Eu1 Eu1 3.8708(5) 3_767 ? N1 O7 1.2532(10) . ? N1 O5 1.306(7) . ? N1 O6 1.354(7) . ? O2 Eu1 2.335(4) 3_767 ? O3 Eu1 2.379(4) 4_465 ? O4 Eu1 2.335(4) 1_454 ? O6 Eu1 2.401(4) 3_767 ? O8 H8A 0.8500 . ? O8 H8B 0.8499 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 125.8(6) . . ? O2 C1 C2 117.6(5) . . ? O1 C1 C2 116.7(5) . . ? C3 C2 C1 126.9(5) . . ? C3 C2 S1 112.0(5) . . ? C1 C2 S1 121.1(4) . . ? C2 C3 C4 112.4(6) . . ? C2 C3 H3 123.8 . . ? C4 C3 H3 123.8 . . ? C5 C4 C3 112.6(6) . . ? C5 C4 H4 123.7 . . ? C3 C4 H4 123.7 . . ? C4 C5 C6 128.5(5) . . ? C4 C5 S1 111.6(4) . . ? C6 C5 S1 119.8(4) . . ? O4 C6 O3 124.8(5) . . ? O4 C6 C5 117.0(5) . . ? O3 C6 C5 118.2(5) . . ? O1 Eu1 O2 138.32(15) . 3_767 ? O1 Eu1 O4 141.51(15) . 1_656 ? O2 Eu1 O4 77.37(14) 3_767 1_656 ? O1 Eu1 O3 99.35(16) . 4_666 ? O2 Eu1 O3 97.94(15) 3_767 4_666 ? O4 Eu1 O3 85.50(14) 1_656 4_666 ? O1 Eu1 O8 70.56(15) . . ? O2 Eu1 O8 150.53(14) 3_767 . ? O4 Eu1 O8 73.20(14) 1_656 . ? O3 Eu1 O8 78.28(15) 4_666 . ? O1 Eu1 O6 72.20(16) . 3_767 ? O2 Eu1 O6 75.90(15) 3_767 3_767 ? O4 Eu1 O6 144.53(15) 1_656 3_767 ? O3 Eu1 O6 75.61(14) 4_666 3_767 ? O8 Eu1 O6 129.63(14) . 3_767 ? O1 Eu1 O6 72.52(16) . . ? O2 Eu1 O6 74.24(15) 3_767 . ? O4 Eu1 O6 118.21(14) 1_656 . ? O3 Eu1 O6 151.48(14) 4_666 . ? O8 Eu1 O6 121.80(15) . . ? O6 Eu1 O6 75.88(15) 3_767 . ? O1 Eu1 O5 84.66(16) . . ? O2 Eu1 O5 93.74(16) 3_767 . ? O4 Eu1 O5 77.71(15) 1_656 . ? O3 Eu1 O5 156.93(13) 4_666 . ? O8 Eu1 O5 81.76(14) . . ? O6 Eu1 O5 126.78(14) 3_767 . ? O6 Eu1 O5 51.33(13) . . ? O1 Eu1 Eu1 67.41(11) . 3_767 ? O2 Eu1 Eu1 70.91(10) 3_767 3_767 ? O4 Eu1 Eu1 144.22(10) 1_656 3_767 ? O3 Eu1 Eu1 114.51(10) 4_666 3_767 ? O8 Eu1 Eu1 137.46(11) . 3_767 ? O6 Eu1 Eu1 38.90(10) 3_767 3_767 ? O6 Eu1 Eu1 36.98(9) . 3_767 ? O5 Eu1 Eu1 88.10(9) . 3_767 ? O7 N1 O5 125.4(6) . . ? O7 N1 O6 124.9(6) . . ? O5 N1 O6 109.7(4) . . ? C1 O1 Eu1 141.3(4) . . ? C1 O2 Eu1 134.6(4) . 3_767 ? C6 O3 Eu1 136.0(4) . 4_465 ? C6 O4 Eu1 148.3(4) . 1_454 ? N1 O6 Eu1 153.5(4) . 3_767 ? N1 O6 Eu1 98.3(3) . . ? Eu1 O6 Eu1 104.12(15) 3_767 . ? N1 O5 Eu1 99.3(3) . . ? Eu1 O8 H8A 119.9 . . ? Eu1 O8 H8B 120.1 . . ? H8A O8 H8B 120.0 . . ? C2 S1 C5 91.3(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.149 _refine_diff_density_min -3.014 _refine_diff_density_rms 0.221 data_5 _database_code_depnum_ccdc_archive 'CCDC 798443' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Gd N O8 S' _chemical_formula_weight 407.41 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' Gd Gd -0.1653 3.9035 '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' _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 9.918(5) _cell_length_b 14.312(7) _cell_length_c 7.712(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.036(7) _cell_angle_gamma 90.00 _cell_volume 1066.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1847 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 50.02 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 6.445 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6984 _exptl_absorpt_correction_T_max 0.7826 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6751 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1847 _reflns_number_gt 1829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0408P)^2^+4.7414P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0050(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1847 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _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 0.6953(5) 0.2407(3) 0.5586(6) 0.0075(9) Uani 1 1 d . . . C2 C 0.5564(5) 0.2301(3) 0.4399(6) 0.0094(9) Uani 1 1 d . . . C3 C 0.4710(5) 0.2981(3) 0.3503(6) 0.0115(9) Uani 1 1 d . . . H3 H 0.4941 0.3611 0.3530 0.014 Uiso 1 1 calc R . . C4 C 0.3453(5) 0.2621(3) 0.2546(6) 0.0131(10) Uani 1 1 d . . . H4 H 0.2752 0.2989 0.1877 0.016 Uiso 1 1 calc R . . C5 C 0.3358(5) 0.1675(3) 0.2691(6) 0.0091(9) Uani 1 1 d . . . C6 C 0.2210(5) 0.1059(3) 0.1780(7) 0.0097(10) Uani 1 1 d . . . Gd1 Gd 0.90358(2) 0.112410(14) 0.89560(3) 0.00468(14) Uani 1 1 d . . . N1 N 1.1046(5) 0.0302(3) 0.7249(6) 0.0197(10) Uani 1 1 d . . . O1 O 0.7431(3) 0.1710(2) 0.6506(4) 0.0091(7) Uani 1 1 d . . . O2 O 0.7573(3) 0.3183(2) 0.5598(4) 0.0088(7) Uani 1 1 d . . . O3 O 0.2348(3) 0.0191(2) 0.2057(4) 0.0123(7) Uani 1 1 d . . . O4 O 0.1199(3) 0.1459(2) 0.0788(4) 0.0125(7) Uani 1 1 d . . . O5 O 1.0356(4) 0.1016(2) 0.6620(5) 0.0101(7) Uani 1 1 d . . . O6 O 1.0685(3) -0.0147(2) 0.8502(4) 0.0093(7) Uani 1 1 d . . . O7 O 1.2275(5) -0.0021(4) 0.6573(7) 0.0423(12) Uani 1 1 d . . . O8 O 0.9540(4) 0.2762(2) 0.8753(4) 0.0115(7) Uani 1 1 d . . . H8A H 1.0210 0.2919 0.8311 0.017 Uiso 1 1 d R . . H8B H 0.9084 0.3184 0.9143 0.017 Uiso 1 1 d R . . S1 S 0.48174(12) 0.12117(8) 0.40555(16) 0.0089(3) 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 C1 0.007(2) 0.008(2) 0.008(2) -0.0010(18) 0.0049(17) 0.0012(18) C2 0.007(2) 0.010(2) 0.010(2) -0.0009(18) 0.0015(17) -0.0019(18) C3 0.008(2) 0.010(2) 0.015(2) 0.0018(18) -0.0013(18) -0.0014(18) C4 0.011(2) 0.008(2) 0.019(2) 0.0031(19) -0.0010(19) 0.0022(18) C5 0.004(2) 0.011(2) 0.011(2) 0.0005(18) -0.0003(17) 0.0006(18) C6 0.006(2) 0.009(3) 0.013(2) 0.0023(17) 0.0006(19) -0.0014(16) Gd1 0.00338(18) 0.00341(18) 0.00665(18) 0.00026(7) -0.00016(11) 0.00039(7) N1 0.019(2) 0.021(2) 0.019(2) -0.0027(19) 0.0023(18) -0.0027(19) O1 0.0075(16) 0.0068(15) 0.0106(16) 0.0015(13) -0.0030(12) -0.0003(13) O2 0.0071(15) 0.0073(16) 0.0116(16) -0.0002(13) 0.0011(12) -0.0026(13) O3 0.0102(16) 0.0060(17) 0.0172(17) 0.0014(13) -0.0043(14) -0.0008(13) O4 0.0070(16) 0.0112(18) 0.0157(17) 0.0025(14) -0.0049(13) 0.0003(14) O5 0.0106(17) 0.0066(16) 0.0137(18) 0.0046(12) 0.0037(14) 0.0027(13) O6 0.0124(17) 0.0087(16) 0.0081(15) 0.0034(12) 0.0051(13) 0.0039(13) O7 0.040(3) 0.043(3) 0.049(3) 0.000(2) 0.018(2) 0.005(2) O8 0.0155(17) 0.0044(16) 0.0150(16) 0.0010(13) 0.0041(13) -0.0001(13) S1 0.0065(6) 0.0056(6) 0.0126(6) 0.0010(4) -0.0020(5) -0.0003(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 O1 1.253(6) . ? C1 O2 1.269(6) . ? C1 C2 1.480(6) . ? C2 C3 1.370(7) . ? C2 S1 1.720(5) . ? C3 C4 1.396(7) . ? C3 H3 0.9300 . ? C4 C5 1.363(7) . ? C4 H4 0.9300 . ? C5 C6 1.485(7) . ? C5 S1 1.719(5) . ? C6 O4 1.253(6) . ? C6 O3 1.263(6) . ? Gd1 O1 2.334(3) . ? Gd1 O4 2.337(3) 1_656 ? Gd1 O2 2.349(3) 4_566 ? Gd1 O3 2.357(3) 3_656 ? Gd1 O6 2.373(3) 3_757 ? Gd1 O8 2.409(3) . ? Gd1 O5 2.459(4) . ? Gd1 O6 2.523(3) . ? Gd1 N1 2.877(5) . ? Gd1 Gd1 3.9006(14) 3_757 ? N1 O5 1.264(6) . ? N1 O6 1.277(6) . ? N1 O7 1.503(6) . ? O2 Gd1 2.349(3) 4_565 ? O3 Gd1 2.357(3) 3_656 ? O4 Gd1 2.337(3) 1_454 ? O6 Gd1 2.373(3) 3_757 ? O8 H8A 0.8433 . ? O8 H8B 0.8494 . ? 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 124.9(4) . . ? O1 C1 C2 116.7(4) . . ? O2 C1 C2 118.5(4) . . ? C3 C2 C1 128.4(4) . . ? C3 C2 S1 111.7(3) . . ? C1 C2 S1 119.8(3) . . ? C2 C3 C4 112.4(4) . . ? C2 C3 H3 123.8 . . ? C4 C3 H3 123.8 . . ? C5 C4 C3 113.2(4) . . ? C5 C4 H4 123.4 . . ? C3 C4 H4 123.4 . . ? C4 C5 C6 127.6(4) . . ? C4 C5 S1 111.6(4) . . ? C6 C5 S1 120.7(4) . . ? O4 C6 O3 126.4(5) . . ? O4 C6 C5 116.1(4) . . ? O3 C6 C5 117.5(4) . . ? O1 Gd1 O4 141.35(12) . 1_656 ? O1 Gd1 O2 83.87(11) . 4_566 ? O4 Gd1 O2 100.49(12) 1_656 4_566 ? O1 Gd1 O3 77.24(11) . 3_656 ? O4 Gd1 O3 138.65(12) 1_656 3_656 ? O2 Gd1 O3 97.55(12) 4_566 3_656 ? O1 Gd1 O6 144.26(11) . 3_757 ? O4 Gd1 O6 72.60(12) 1_656 3_757 ? O2 Gd1 O6 76.98(11) 4_566 3_757 ? O3 Gd1 O6 75.75(12) 3_656 3_757 ? O1 Gd1 O8 73.23(11) . . ? O4 Gd1 O8 70.38(12) 1_656 . ? O2 Gd1 O8 77.68(12) 4_566 . ? O3 Gd1 O8 150.40(11) 3_656 . ? O6 Gd1 O8 129.77(11) 3_757 . ? O1 Gd1 O5 78.93(12) . . ? O4 Gd1 O5 83.56(13) 1_656 . ? O2 Gd1 O5 156.45(11) 4_566 . ? O3 Gd1 O5 94.23(12) 3_656 . ? O6 Gd1 O5 125.88(11) 3_757 . ? O8 Gd1 O5 82.00(11) . . ? O1 Gd1 O6 119.46(11) . . ? O4 Gd1 O6 72.31(12) 1_656 . ? O2 Gd1 O6 151.35(10) 4_566 . ? O3 Gd1 O6 74.07(12) 3_656 . ? O6 Gd1 O6 74.41(12) 3_757 . ? O8 Gd1 O6 122.82(11) . . ? O5 Gd1 O6 51.99(10) . . ? O1 Gd1 N1 101.12(12) . . ? O4 Gd1 N1 73.98(13) 1_656 . ? O2 Gd1 N1 174.35(12) 4_566 . ? O3 Gd1 N1 86.20(13) 3_656 . ? O6 Gd1 N1 99.99(12) 3_757 . ? O8 Gd1 N1 101.11(12) . . ? O5 Gd1 N1 25.93(12) . . ? O6 Gd1 N1 26.34(12) . . ? O1 Gd1 Gd1 144.28(8) . 3_757 ? O4 Gd1 Gd1 67.76(9) 1_656 3_757 ? O2 Gd1 Gd1 115.51(8) 4_566 3_757 ? O3 Gd1 Gd1 70.89(9) 3_656 3_757 ? O6 Gd1 Gd1 38.54(8) 3_757 3_757 ? O8 Gd1 Gd1 137.71(8) . 3_757 ? O5 Gd1 Gd1 87.61(8) . 3_757 ? O6 Gd1 Gd1 35.87(7) . 3_757 ? N1 Gd1 Gd1 61.69(9) . 3_757 ? O5 N1 O6 118.5(4) . . ? O5 N1 O7 121.8(4) . . ? O6 N1 O7 119.7(4) . . ? O5 N1 Gd1 58.2(2) . . ? O6 N1 Gd1 61.2(2) . . ? O7 N1 Gd1 169.9(3) . . ? C1 O1 Gd1 147.8(3) . . ? C1 O2 Gd1 136.3(3) . 4_565 ? C6 O3 Gd1 134.2(3) . 3_656 ? C6 O4 Gd1 140.7(3) . 1_454 ? N1 O5 Gd1 95.8(3) . . ? N1 O6 Gd1 157.1(3) . 3_757 ? N1 O6 Gd1 92.5(3) . . ? Gd1 O6 Gd1 105.59(12) 3_757 . ? Gd1 O8 H8A 118.6 . . ? Gd1 O8 H8B 122.3 . . ? H8A O8 H8B 119.0 . . ? C5 S1 C2 91.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 167.6(5) . . . . ? O2 C1 C2 C3 -12.8(7) . . . . ? O1 C1 C2 S1 -10.8(6) . . . . ? O2 C1 C2 S1 168.9(3) . . . . ? C1 C2 C3 C4 -178.2(4) . . . . ? S1 C2 C3 C4 0.2(5) . . . . ? C2 C3 C4 C5 -0.8(6) . . . . ? C3 C4 C5 C6 -176.4(5) . . . . ? C3 C4 C5 S1 1.1(6) . . . . ? C4 C5 C6 O4 -1.5(8) . . . . ? S1 C5 C6 O4 -178.8(4) . . . . ? C4 C5 C6 O3 177.7(5) . . . . ? S1 C5 C6 O3 0.4(6) . . . . ? O1 Gd1 N1 O5 31.6(3) . . . . ? O4 Gd1 N1 O5 -108.9(3) 1_656 . . . ? O2 Gd1 N1 O5 -120.4(12) 4_566 . . . ? O3 Gd1 N1 O5 107.8(3) 3_656 . . . ? O6 Gd1 N1 O5 -177.4(3) 3_757 . . . ? O8 Gd1 N1 O5 -43.3(3) . . . . ? O6 Gd1 N1 O5 168.7(4) . . . . ? Gd1 Gd1 N1 O5 178.1(3) 3_757 . . . ? O1 Gd1 N1 O6 -137.1(2) . . . . ? O4 Gd1 N1 O6 82.4(3) 1_656 . . . ? O2 Gd1 N1 O6 70.9(13) 4_566 . . . ? O3 Gd1 N1 O6 -60.9(3) 3_656 . . . ? O6 Gd1 N1 O6 13.9(3) 3_757 . . . ? O8 Gd1 N1 O6 148.0(2) . . . . ? O5 Gd1 N1 O6 -168.7(4) . . . . ? Gd1 Gd1 N1 O6 9.4(2) 3_757 . . . ? O1 Gd1 N1 O7 125.1(19) . . . . ? O4 Gd1 N1 O7 -15.4(19) 1_656 . . . ? O2 Gd1 N1 O7 -27(3) 4_566 . . . ? O3 Gd1 N1 O7 -158.7(19) 3_656 . . . ? O6 Gd1 N1 O7 -83.9(19) 3_757 . . . ? O8 Gd1 N1 O7 50.3(19) . . . . ? O5 Gd1 N1 O7 93.5(19) . . . . ? O6 Gd1 N1 O7 -97.8(19) . . . . ? Gd1 Gd1 N1 O7 -88.4(19) 3_757 . . . ? O2 C1 O1 Gd1 18.3(8) . . . . ? C2 C1 O1 Gd1 -162.1(4) . . . . ? O4 Gd1 O1 C1 -24.6(6) 1_656 . . . ? O2 Gd1 O1 C1 74.5(6) 4_566 . . . ? O3 Gd1 O1 C1 173.7(6) 3_656 . . . ? O6 Gd1 O1 C1 132.0(5) 3_757 . . . ? O8 Gd1 O1 C1 -4.4(5) . . . . ? O5 Gd1 O1 C1 -89.3(6) . . . . ? O6 Gd1 O1 C1 -123.1(5) . . . . ? N1 Gd1 O1 C1 -102.8(6) . . . . ? Gd1 Gd1 O1 C1 -159.2(5) 3_757 . . . ? O1 C1 O2 Gd1 92.7(5) . . . 4_565 ? C2 C1 O2 Gd1 -86.9(5) . . . 4_565 ? O4 C6 O3 Gd1 -0.6(8) . . . 3_656 ? C5 C6 O3 Gd1 -179.6(3) . . . 3_656 ? O3 C6 O4 Gd1 2.3(9) . . . 1_454 ? C5 C6 O4 Gd1 -178.6(3) . . . 1_454 ? O6 N1 O5 Gd1 11.3(4) . . . . ? O7 N1 O5 Gd1 -168.2(4) . . . . ? O1 Gd1 O5 N1 -148.4(3) . . . . ? O4 Gd1 O5 N1 66.2(3) 1_656 . . . ? O2 Gd1 O5 N1 167.7(3) 4_566 . . . ? O3 Gd1 O5 N1 -72.3(3) 3_656 . . . ? O6 Gd1 O5 N1 3.2(3) 3_757 . . . ? O8 Gd1 O5 N1 137.2(3) . . . . ? O6 Gd1 O5 N1 -6.3(2) . . . . ? Gd1 Gd1 O5 N1 -1.7(3) 3_757 . . . ? O5 N1 O6 Gd1 -153.5(6) . . . 3_757 ? O7 N1 O6 Gd1 25.9(10) . . . 3_757 ? Gd1 N1 O6 Gd1 -142.6(8) . . . 3_757 ? O5 N1 O6 Gd1 -10.9(4) . . . . ? O7 N1 O6 Gd1 168.5(4) . . . . ? O1 Gd1 O6 N1 50.1(3) . . . . ? O4 Gd1 O6 N1 -89.5(3) 1_656 . . . ? O2 Gd1 O6 N1 -168.8(3) 4_566 . . . ? O3 Gd1 O6 N1 114.9(3) 3_656 . . . ? O6 Gd1 O6 N1 -165.8(3) 3_757 . . . ? O8 Gd1 O6 N1 -38.2(3) . . . . ? O5 Gd1 O6 N1 6.2(2) . . . . ? Gd1 Gd1 O6 N1 -165.8(3) 3_757 . . . ? O1 Gd1 O6 Gd1 -144.11(12) . . . 3_757 ? O4 Gd1 O6 Gd1 76.30(14) 1_656 . . 3_757 ? O2 Gd1 O6 Gd1 -3.0(3) 4_566 . . 3_757 ? O3 Gd1 O6 Gd1 -79.27(13) 3_656 . . 3_757 ? O6 Gd1 O6 Gd1 0.0 3_757 . . 3_757 ? O8 Gd1 O6 Gd1 127.62(12) . . . 3_757 ? O5 Gd1 O6 Gd1 172.04(19) . . . 3_757 ? N1 Gd1 O6 Gd1 165.8(3) . . . 3_757 ? C4 C5 S1 C2 -0.8(4) . . . . ? C6 C5 S1 C2 176.9(4) . . . . ? C3 C2 S1 C5 0.4(4) . . . . ? C1 C2 S1 C5 178.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.761 _refine_diff_density_min -0.986 _refine_diff_density_rms 0.168 data_6 _database_code_depnum_ccdc_archive 'CCDC 798444' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 N O8 S Tb' _chemical_formula_weight 409.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb -0.1943 3.0179 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 9.971(3) _cell_length_b 14.389(4) _cell_length_c 7.971(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.982(6) _cell_angle_gamma 90.00 _cell_volume 1109.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1949 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 24.99 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 6.59 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4122 _exptl_absorpt_correction_T_max 0.4727 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method 0 _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6112 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0709 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1949 _reflns_number_gt 1580 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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^)+(0.0554P)^2^+2.7584P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1949 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _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 0.6994(4) 0.2386(3) 0.5571(5) 0.0235(13) Uani 1 1 d . . . C2 C 0.5581(5) 0.2287(3) 0.4438(6) 0.0261(13) Uani 1 1 d . . . C3 C 0.4733(5) 0.2963(3) 0.3532(6) 0.0313(14) Uani 1 1 d . . . H3 H 0.4981 0.3585 0.3522 0.038 Uiso 1 1 calc R . . C4 C 0.3445(5) 0.2609(3) 0.2623(6) 0.0340(15) Uani 1 1 d . . . H4 H 0.2744 0.2972 0.1955 0.041 Uiso 1 1 calc R . . C5 C 0.3345(4) 0.1653(3) 0.2840(6) 0.0273(12) Uani 1 1 d U . . C6 C 0.2153(5) 0.1054(3) 0.2013(7) 0.0327(14) Uani 1 1 d . . . N1 N 1.1094(4) 0.0330(3) 0.7399(5) 0.0417(14) Uani 1 1 d . . . O1 O 0.7487(3) 0.17081(18) 0.6542(4) 0.0240(9) Uani 1 1 d . . . O2 O 0.7632(3) 0.31518(19) 0.5519(4) 0.0273(9) Uani 1 1 d . . . O3 O 0.2276(3) 0.01733(19) 0.2192(4) 0.0347(10) Uani 1 1 d . . . O4 O 0.1102(3) 0.1465(2) 0.1083(4) 0.0395(10) Uani 1 1 d U . . O5 O 1.0409(3) 0.10543(19) 0.6769(4) 0.0309(9) Uani 1 1 d . . . O6 O 1.0799(3) -0.00797(19) 0.8699(4) 0.0268(9) Uani 1 1 d . . . O7 O 1.2280(5) -0.0043(3) 0.6618(6) 0.0970(19) Uani 1 1 d . . . O8 O 0.9654(3) 0.2756(2) 0.8854(4) 0.0343(10) Uani 1 1 d . . . H8A H 1.0324 0.2913 0.8411 0.051 Uiso 1 1 d R . . H8B H 0.9198 0.3178 0.9243 0.051 Uiso 1 1 d R . . S1 S 0.48026(12) 0.11950(7) 0.41611(15) 0.0282(3) Uani 1 1 d . . . Tb1 Tb 0.90525(2) 0.113458(13) 0.89723(3) 0.01810(5) 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 C1 0.016(2) 0.026(2) 0.028(2) 0.0034(19) 0.0043(18) -0.0037(19) C2 0.024(2) 0.024(2) 0.026(2) 0.0099(19) -0.0010(19) -0.005(2) C3 0.023(3) 0.023(2) 0.039(3) 0.012(2) -0.011(2) 0.004(2) C4 0.016(2) 0.022(2) 0.051(3) 0.004(2) -0.019(2) -0.001(2) C5 0.013(2) 0.030(2) 0.029(2) -0.0005(19) -0.0149(18) -0.0029(19) C6 0.025(2) 0.020(2) 0.046(3) 0.001(2) -0.007(2) -0.011(2) N1 0.027(2) 0.055(3) 0.043(2) -0.007(2) 0.0070(19) -0.006(2) O1 0.0195(15) 0.0180(14) 0.0256(15) 0.0039(13) -0.0116(13) -0.0029(13) O2 0.0188(15) 0.0240(15) 0.0323(17) 0.0025(13) -0.0071(14) -0.0076(14) O3 0.0249(17) 0.0168(14) 0.050(2) -0.0020(15) -0.0146(16) -0.0020(14) O4 0.0234(18) 0.0255(15) 0.0513(19) 0.0007(15) -0.0268(16) 0.0011(14) O5 0.0341(17) 0.0237(15) 0.0312(16) 0.0133(14) 0.0008(14) 0.0144(15) O6 0.0335(17) 0.0279(15) 0.0222(14) 0.0139(13) 0.0127(13) 0.0048(14) O7 0.084(3) 0.107(4) 0.116(4) -0.009(3) 0.057(3) 0.013(3) O8 0.0364(18) 0.0224(15) 0.0392(18) 0.0009(15) -0.0005(15) 0.0000(15) S1 0.0212(6) 0.0194(5) 0.0347(6) 0.0019(5) -0.0113(5) -0.0033(5) Tb1 0.01312(9) 0.01670(8) 0.01945(9) 0.00033(10) -0.00587(8) 0.00111(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.268(5) . ? C1 O2 1.278(5) . ? C1 C2 1.485(6) . ? C2 C3 1.374(6) . ? C2 S1 1.743(4) . ? C3 C4 1.408(6) . ? C3 H3 0.9300 . ? C4 C5 1.393(6) . ? C4 H4 0.9300 . ? C5 C6 1.487(6) . ? C5 S1 1.707(4) . ? C6 O4 1.273(5) . ? C6 O3 1.278(5) . ? N1 O5 1.280(5) . ? N1 O6 1.286(5) . ? N1 O7 1.560(7) . ? O1 Tb1 2.326(3) . ? O2 Tb1 2.329(3) 4_565 ? O3 Tb1 2.359(3) 3_656 ? O4 Tb1 2.361(3) 1_454 ? O5 Tb1 2.465(3) . ? O6 Tb1 2.374(3) 3_757 ? O6 Tb1 2.513(3) . ? O8 Tb1 2.416(3) . ? O8 H8A 0.8579 . ? O8 H8B 0.8606 . ? Tb1 O2 2.329(3) 4_566 ? Tb1 O3 2.359(3) 3_656 ? Tb1 O4 2.361(3) 1_656 ? Tb1 O6 2.374(3) 3_757 ? Tb1 Tb1 3.9268(9) 3_757 ? 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 124.1(4) . . ? O1 C1 C2 117.9(4) . . ? O2 C1 C2 118.0(4) . . ? C3 C2 C1 128.6(4) . . ? C3 C2 S1 111.9(3) . . ? C1 C2 S1 119.5(3) . . ? C2 C3 C4 112.6(4) . . ? C2 C3 H3 123.7 . . ? C4 C3 H3 123.7 . . ? C5 C4 C3 112.1(4) . . ? C5 C4 H4 123.9 . . ? C3 C4 H4 123.9 . . ? C4 C5 C6 126.2(4) . . ? C4 C5 S1 112.5(3) . . ? C6 C5 S1 121.3(3) . . ? O4 C6 O3 124.7(4) . . ? O4 C6 C5 116.5(4) . . ? O3 C6 C5 118.7(4) . . ? O5 N1 O6 119.0(4) . . ? O5 N1 O7 120.5(4) . . ? O6 N1 O7 120.4(4) . . ? C1 O1 Tb1 149.8(3) . . ? C1 O2 Tb1 140.2(3) . 4_565 ? C6 O3 Tb1 135.8(3) . 3_656 ? C6 O4 Tb1 140.4(3) . 1_454 ? N1 O5 Tb1 95.2(3) . . ? N1 O6 Tb1 160.0(3) . 3_757 ? N1 O6 Tb1 92.8(2) . . ? Tb1 O6 Tb1 106.88(12) 3_757 . ? Tb1 O8 H8A 119.7 . . ? Tb1 O8 H8B 120.6 . . ? H8A O8 H8B 119.7 . . ? C5 S1 C2 91.0(2) . . ? O1 Tb1 O2 84.98(10) . 4_566 ? O1 Tb1 O3 75.83(10) . 3_656 ? O2 Tb1 O3 101.79(11) 4_566 3_656 ? O1 Tb1 O4 144.44(10) . 1_656 ? O2 Tb1 O4 93.81(11) 4_566 1_656 ? O3 Tb1 O4 138.46(10) 3_656 1_656 ? O1 Tb1 O6 141.29(10) . 3_757 ? O2 Tb1 O6 78.41(10) 4_566 3_757 ? O3 Tb1 O6 73.77(11) 3_656 3_757 ? O4 Tb1 O6 72.06(11) 1_656 3_757 ? O1 Tb1 O8 75.40(10) . . ? O2 Tb1 O8 77.49(11) 4_566 . ? O3 Tb1 O8 151.16(10) 3_656 . ? O4 Tb1 O8 69.70(10) 1_656 . ? O6 Tb1 O8 132.73(10) 3_757 . ? O1 Tb1 O5 78.28(10) . . ? O2 Tb1 O5 155.02(10) 4_566 . ? O3 Tb1 O5 92.01(11) 3_656 . ? O4 Tb1 O5 89.29(12) 1_656 . ? O6 Tb1 O5 125.85(10) 3_757 . ? O8 Tb1 O5 80.40(11) . . ? O1 Tb1 O6 120.96(10) . . ? O2 Tb1 O6 151.06(10) 4_566 . ? O3 Tb1 O6 75.31(10) 3_656 . ? O4 Tb1 O6 72.73(10) 1_656 . ? O6 Tb1 O6 73.12(12) 3_757 . ? O8 Tb1 O6 118.96(11) . . ? O5 Tb1 O6 52.75(9) . . ? O1 Tb1 Tb1 143.23(7) . 3_757 ? O2 Tb1 Tb1 116.02(7) 4_566 3_757 ? O3 Tb1 Tb1 70.65(7) 3_656 3_757 ? O4 Tb1 Tb1 67.90(8) 1_656 3_757 ? O6 Tb1 Tb1 37.77(7) 3_757 3_757 ? O8 Tb1 Tb1 136.07(8) . 3_757 ? O5 Tb1 Tb1 88.09(7) . 3_757 ? O6 Tb1 Tb1 35.35(7) . 3_757 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 166.6(5) . . . . ? O2 C1 C2 C3 -12.8(8) . . . . ? O1 C1 C2 S1 -12.5(6) . . . . ? O2 C1 C2 S1 168.1(3) . . . . ? C1 C2 C3 C4 -178.6(5) . . . . ? S1 C2 C3 C4 0.6(6) . . . . ? C2 C3 C4 C5 -0.8(7) . . . . ? C3 C4 C5 C6 -177.6(5) . . . . ? C3 C4 C5 S1 0.7(6) . . . . ? C4 C5 C6 O4 -3.5(8) . . . . ? S1 C5 C6 O4 178.4(4) . . . . ? C4 C5 C6 O3 172.5(5) . . . . ? S1 C5 C6 O3 -5.6(7) . . . . ? O2 C1 O1 Tb1 20.3(9) . . . . ? C2 C1 O1 Tb1 -159.1(4) . . . . ? O1 C1 O2 Tb1 93.9(5) . . . 4_565 ? C2 C1 O2 Tb1 -86.7(5) . . . 4_565 ? O4 C6 O3 Tb1 3.6(9) . . . 3_656 ? C5 C6 O3 Tb1 -172.0(3) . . . 3_656 ? O3 C6 O4 Tb1 -10.9(9) . . . 1_454 ? C5 C6 O4 Tb1 164.8(4) . . . 1_454 ? O6 N1 O5 Tb1 4.5(4) . . . . ? O7 N1 O5 Tb1 -174.8(3) . . . . ? O5 N1 O6 Tb1 -173.6(5) . . . 3_757 ? O7 N1 O6 Tb1 5.6(10) . . . 3_757 ? O5 N1 O6 Tb1 -4.4(4) . . . . ? O7 N1 O6 Tb1 174.9(3) . . . . ? C4 C5 S1 C2 -0.3(4) . . . . ? C6 C5 S1 C2 178.1(4) . . . . ? C3 C2 S1 C5 -0.2(4) . . . . ? C1 C2 S1 C5 179.1(4) . . . . ? C1 O1 Tb1 O2 74.2(6) . . . 4_566 ? C1 O1 Tb1 O3 177.7(6) . . . 3_656 ? C1 O1 Tb1 O4 -15.3(7) . . . 1_656 ? C1 O1 Tb1 O6 138.6(6) . . . 3_757 ? C1 O1 Tb1 O8 -4.1(6) . . . . ? C1 O1 Tb1 O5 -87.1(6) . . . . ? C1 O1 Tb1 O6 -119.4(6) . . . . ? C1 O1 Tb1 Tb1 -157.6(5) . . . 3_757 ? N1 O5 Tb1 O1 -147.4(2) . . . . ? N1 O5 Tb1 O2 163.7(2) . . . 4_566 ? N1 O5 Tb1 O3 -72.3(2) . . . 3_656 ? N1 O5 Tb1 O4 66.2(2) . . . 1_656 ? N1 O5 Tb1 O6 -0.9(3) . . . 3_757 ? N1 O5 Tb1 O8 135.7(2) . . . . ? N1 O5 Tb1 O6 -2.5(2) . . . . ? N1 O5 Tb1 Tb1 -1.7(2) . . . 3_757 ? N1 O6 Tb1 O1 43.6(2) . . . . ? Tb1 O6 Tb1 O1 -140.26(10) 3_757 . . . ? N1 O6 Tb1 O2 -165.5(2) . . . 4_566 ? Tb1 O6 Tb1 O2 10.7(2) 3_757 . . 4_566 ? N1 O6 Tb1 O3 106.7(2) . . . 3_656 ? Tb1 O6 Tb1 O3 -77.16(13) 3_757 . . 3_656 ? N1 O6 Tb1 O4 -100.2(2) . . . 1_656 ? Tb1 O6 Tb1 O4 75.95(12) 3_757 . . 1_656 ? N1 O6 Tb1 O6 -176.2(3) . . . 3_757 ? Tb1 O6 Tb1 O6 0.0 3_757 . . 3_757 ? N1 O6 Tb1 O8 -46.2(2) . . . . ? Tb1 O6 Tb1 O8 129.98(11) 3_757 . . . ? N1 O6 Tb1 O5 2.5(2) . . . . ? Tb1 O6 Tb1 O5 178.66(16) 3_757 . . . ? N1 O6 Tb1 Tb1 -176.2(3) . . . 3_757 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.251 _refine_diff_density_min -1.700 _refine_diff_density_rms 0.229 data_7 _database_code_depnum_ccdc_archive 'CCDC 798445' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Dy N O8 S' _chemical_formula_weight 412.66 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' Dy Dy -0.1892 4.4098 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/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 9.8979(7) _cell_length_b 14.2167(11) _cell_length_c 7.9086(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.093(2) _cell_angle_gamma 90.00 _cell_volume 1079.37(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2467 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 7.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2230 _exptl_absorpt_correction_T_max 0.2903 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7475 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2467 _reflns_number_gt 2052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0265P)^2^+7.0957P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2467 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 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 0.7007(8) 0.2392(5) 0.5569(10) 0.0182(16) Uani 1 1 d . . . C2 C 0.5593(8) 0.2292(5) 0.4426(10) 0.0217(17) Uani 1 1 d . . . C3 C 0.4746(9) 0.2951(6) 0.3501(11) 0.029(2) Uani 1 1 d . . . H3 H 0.5001 0.3581 0.3466 0.035 Uiso 1 1 calc R . . C4 C 0.3447(9) 0.2604(6) 0.2596(12) 0.031(2) Uani 1 1 d . . . H4 H 0.2738 0.2975 0.1928 0.037 Uiso 1 1 calc R . . C5 C 0.3349(8) 0.1650(6) 0.2814(10) 0.0227(17) Uani 1 1 d . . . C6 C 0.2161(9) 0.1054(5) 0.1964(11) 0.0229(17) Uani 1 1 d . . . Dy1 Dy 0.90595(4) 0.11338(2) 0.89682(5) 0.01479(12) Uani 1 1 d . . . N1 N 1.1098(8) 0.0324(5) 0.7410(11) 0.0367(19) Uani 1 1 d . . . O1 O 0.7498(6) 0.1710(4) 0.6551(7) 0.0252(13) Uani 1 1 d . . . O2 O 0.7647(6) 0.3153(4) 0.5495(7) 0.0233(13) Uani 1 1 d . . . O3 O 0.2273(6) 0.0173(4) 0.2202(8) 0.0308(15) Uani 1 1 d . . . O4 O 0.1107(6) 0.1462(4) 0.1063(8) 0.0351(16) Uani 1 1 d . . . O5 O 1.0406(6) 0.1055(4) 0.6769(8) 0.0279(13) Uani 1 1 d . . . O6 O 1.0798(6) -0.0082(4) 0.8700(7) 0.0249(13) Uani 1 1 d . . . O7 O 1.2270(11) -0.0050(7) 0.6646(13) 0.087(3) Uani 1 1 d . . . O8 O 0.9659(7) 0.2756(4) 0.8828(7) 0.0286(14) Uani 1 1 d . . . H8A H 1.0329 0.2913 0.8385 0.043 Uiso 1 1 d R . . H8B H 0.9202 0.3178 0.9217 0.043 Uiso 1 1 d R . . S1 S 0.4814(2) 0.11927(14) 0.4156(3) 0.0238(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.015(4) 0.020(4) 0.018(4) -0.001(3) 0.001(3) -0.002(3) C2 0.017(4) 0.018(4) 0.027(4) -0.001(3) -0.001(4) -0.007(3) C3 0.027(5) 0.017(4) 0.036(5) 0.009(4) -0.008(4) -0.001(4) C4 0.018(5) 0.023(4) 0.041(5) 0.004(4) -0.015(4) 0.001(4) C5 0.016(4) 0.025(4) 0.022(4) 0.004(3) -0.007(3) 0.001(4) C6 0.016(4) 0.015(4) 0.033(4) -0.001(3) -0.004(3) 0.001(3) Dy1 0.01144(19) 0.01294(17) 0.01711(18) 0.00008(15) -0.00208(13) 0.00096(17) N1 0.028(5) 0.038(4) 0.041(5) -0.007(4) 0.002(4) -0.004(4) O1 0.014(3) 0.021(3) 0.033(3) 0.008(2) -0.010(2) 0.000(2) O2 0.017(3) 0.022(3) 0.029(3) 0.001(2) 0.002(2) -0.011(2) O3 0.019(3) 0.013(3) 0.050(4) 0.002(3) -0.011(3) -0.004(2) O4 0.016(3) 0.020(3) 0.055(4) 0.005(3) -0.019(3) 0.003(3) O5 0.029(3) 0.025(3) 0.031(3) 0.009(3) 0.010(3) 0.011(3) O6 0.028(3) 0.028(3) 0.023(3) 0.013(2) 0.014(3) 0.010(3) O7 0.093(8) 0.083(7) 0.102(8) -0.004(6) 0.057(7) 0.016(6) O8 0.035(4) 0.022(3) 0.027(3) 0.003(2) 0.003(3) -0.006(3) S1 0.0162(11) 0.0153(9) 0.0335(11) 0.0028(8) -0.0065(9) -0.0019(9) _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 1.259(9) . ? C1 O2 1.257(9) . ? C1 C2 1.473(11) . ? C2 C3 1.344(11) . ? C2 S1 1.726(8) . ? C3 C4 1.396(11) . ? C3 H3 0.9300 . ? C4 C5 1.368(11) . ? C4 H4 0.9300 . ? C5 C6 1.468(11) . ? C5 S1 1.699(8) . ? C6 O3 1.262(8) . ? C6 O4 1.249(9) . ? Dy1 O2 2.289(5) 4_566 ? Dy1 O1 2.290(5) . ? Dy1 O4 2.326(6) 1_656 ? Dy1 O3 2.327(5) 3_656 ? Dy1 O6 2.343(5) 3_757 ? Dy1 O8 2.381(5) . ? Dy1 O5 2.433(6) . ? Dy1 O6 2.477(5) . ? Dy1 N1 2.844(8) . ? Dy1 Dy1 3.8785(5) 3_757 ? N1 O5 1.275(9) . ? N1 O6 1.265(9) . ? N1 O7 1.525(11) . ? O2 Dy1 2.289(5) 4_565 ? O3 Dy1 2.327(5) 3_656 ? O4 Dy1 2.326(6) 1_454 ? O6 Dy1 2.343(5) 3_757 ? O8 H8A 0.8500 . ? O8 H8B 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 124.3(7) . . ? O1 C1 C2 117.9(7) . . ? O2 C1 C2 117.9(7) . . ? C3 C2 C1 129.6(7) . . ? C3 C2 S1 111.0(6) . . ? C1 C2 S1 119.4(6) . . ? C2 C3 C4 114.0(7) . . ? C2 C3 H3 123.0 . . ? C4 C3 H3 123.0 . . ? C5 C4 C3 111.6(7) . . ? C5 C4 H4 124.2 . . ? C3 C4 H4 124.2 . . ? C4 C5 C6 125.7(7) . . ? C4 C5 S1 112.3(6) . . ? C6 C5 S1 122.0(6) . . ? O3 C6 O4 124.9(8) . . ? O3 C6 C5 118.0(7) . . ? O4 C6 C5 117.1(7) . . ? O2 Dy1 O1 84.7(2) 4_566 . ? O2 Dy1 O4 94.3(2) 4_566 1_656 ? O1 Dy1 O4 144.4(2) . 1_656 ? O2 Dy1 O3 101.6(2) 4_566 3_656 ? O1 Dy1 O3 75.65(19) . 3_656 ? O4 Dy1 O3 138.6(2) 1_656 3_656 ? O2 Dy1 O6 78.18(19) 4_566 3_757 ? O1 Dy1 O6 141.1(2) . 3_757 ? O4 Dy1 O6 72.2(2) 1_656 3_757 ? O3 Dy1 O6 74.1(2) 3_656 3_757 ? O2 Dy1 O8 77.9(2) 4_566 . ? O1 Dy1 O8 75.07(19) . . ? O4 Dy1 O8 69.9(2) 1_656 . ? O3 Dy1 O8 150.6(2) 3_656 . ? O6 Dy1 O8 132.96(19) 3_757 . ? O2 Dy1 O5 154.85(18) 4_566 . ? O1 Dy1 O5 78.3(2) . . ? O4 Dy1 O5 89.0(2) 1_656 . ? O3 Dy1 O5 92.1(2) 3_656 . ? O6 Dy1 O5 126.28(18) 3_757 . ? O8 Dy1 O5 79.9(2) . . ? O2 Dy1 O6 151.18(18) 4_566 . ? O1 Dy1 O6 121.1(2) . . ? O4 Dy1 O6 72.4(2) 1_656 . ? O3 Dy1 O6 75.6(2) 3_656 . ? O6 Dy1 O6 73.4(2) 3_757 . ? O8 Dy1 O6 118.7(2) . . ? O5 Dy1 O6 52.85(17) . . ? O2 Dy1 N1 172.9(2) 4_566 . ? O1 Dy1 N1 100.9(2) . . ? O4 Dy1 N1 78.6(2) 1_656 . ? O3 Dy1 N1 84.3(2) 3_656 . ? O6 Dy1 N1 99.8(2) 3_757 . ? O8 Dy1 N1 99.1(2) . . ? O5 Dy1 N1 26.53(19) . . ? O6 Dy1 N1 26.37(19) . . ? O2 Dy1 Dy1 115.94(13) 4_566 3_757 ? O1 Dy1 Dy1 143.48(14) . 3_757 ? O4 Dy1 Dy1 67.74(14) 1_656 3_757 ? O3 Dy1 Dy1 70.96(14) 3_656 3_757 ? O6 Dy1 Dy1 37.92(13) 3_757 3_757 ? O8 Dy1 Dy1 136.17(15) . 3_757 ? O5 Dy1 Dy1 88.37(13) . 3_757 ? O6 Dy1 Dy1 35.53(12) . 3_757 ? N1 Dy1 Dy1 61.86(17) . 3_757 ? O5 N1 O6 118.7(7) . . ? O5 N1 O7 120.7(8) . . ? O6 N1 O7 120.6(7) . . ? O5 N1 Dy1 58.4(4) . . ? O6 N1 Dy1 60.4(4) . . ? O7 N1 Dy1 175.5(6) . . ? C1 O1 Dy1 150.0(5) . . ? C1 O2 Dy1 141.3(5) . 4_565 ? C6 O3 Dy1 134.9(5) . 3_656 ? C6 O4 Dy1 140.5(5) . 1_454 ? N1 O5 Dy1 95.0(5) . . ? N1 O6 Dy1 159.9(5) . 3_757 ? N1 O6 Dy1 93.2(5) . . ? Dy1 O6 Dy1 106.6(2) 3_757 . ? Dy1 O8 H8A 119.9 . . ? Dy1 O8 H8B 120.1 . . ? H8A O8 H8B 120.0 . . ? C5 S1 C2 91.2(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 167.2(9) . . . . ? O2 C1 C2 C3 -13.1(13) . . . . ? O1 C1 C2 S1 -12.5(10) . . . . ? O2 C1 C2 S1 167.2(6) . . . . ? C1 C2 C3 C4 -178.1(8) . . . . ? S1 C2 C3 C4 1.6(11) . . . . ? C2 C3 C4 C5 -2.1(12) . . . . ? C3 C4 C5 C6 -176.2(8) . . . . ? C3 C4 C5 S1 1.5(11) . . . . ? C4 C5 C6 O3 174.9(9) . . . . ? S1 C5 C6 O3 -2.7(12) . . . . ? C4 C5 C6 O4 -5.5(14) . . . . ? S1 C5 C6 O4 176.9(7) . . . . ? O2 Dy1 N1 O5 -108.3(17) 4_566 . . . ? O1 Dy1 N1 O5 32.3(5) . . . . ? O4 Dy1 N1 O5 -111.4(5) 1_656 . . . ? O3 Dy1 N1 O5 106.4(5) 3_656 . . . ? O6 Dy1 N1 O5 179.1(4) 3_757 . . . ? O8 Dy1 N1 O5 -44.2(5) . . . . ? O6 Dy1 N1 O5 175.2(8) . . . . ? Dy1 Dy1 N1 O5 177.9(5) 3_757 . . . ? O2 Dy1 N1 O6 76.4(18) 4_566 . . . ? O1 Dy1 N1 O6 -143.0(5) . . . . ? O4 Dy1 N1 O6 73.3(5) 1_656 . . . ? O3 Dy1 N1 O6 -68.8(5) 3_656 . . . ? O6 Dy1 N1 O6 3.9(6) 3_757 . . . ? O8 Dy1 N1 O6 140.6(5) . . . . ? O5 Dy1 N1 O6 -175.2(8) . . . . ? Dy1 Dy1 N1 O6 2.6(4) 3_757 . . . ? O2 Dy1 N1 O7 -28(9) 4_566 . . . ? O1 Dy1 N1 O7 113(8) . . . . ? O4 Dy1 N1 O7 -31(8) 1_656 . . . ? O3 Dy1 N1 O7 -173(8) 3_656 . . . ? O6 Dy1 N1 O7 -100(8) 3_757 . . . ? O8 Dy1 N1 O7 36(8) . . . . ? O5 Dy1 N1 O7 80(8) . . . . ? O6 Dy1 N1 O7 -104(8) . . . . ? Dy1 Dy1 N1 O7 -102(8) 3_757 . . . ? O2 C1 O1 Dy1 20.3(16) . . . . ? C2 C1 O1 Dy1 -160.0(7) . . . . ? O2 Dy1 O1 C1 75.2(11) 4_566 . . . ? O4 Dy1 O1 C1 -14.7(12) 1_656 . . . ? O3 Dy1 O1 C1 178.6(11) 3_656 . . . ? O6 Dy1 O1 C1 138.9(10) 3_757 . . . ? O8 Dy1 O1 C1 -3.6(10) . . . . ? O5 Dy1 O1 C1 -86.2(10) . . . . ? O6 Dy1 O1 C1 -118.5(10) . . . . ? N1 Dy1 O1 C1 -100.3(11) . . . . ? Dy1 Dy1 O1 C1 -157.0(9) 3_757 . . . ? O1 C1 O2 Dy1 93.3(10) . . . 4_565 ? C2 C1 O2 Dy1 -86.4(10) . . . 4_565 ? O4 C6 O3 Dy1 8.6(15) . . . 3_656 ? C5 C6 O3 Dy1 -171.8(6) . . . 3_656 ? O3 C6 O4 Dy1 -15.2(16) . . . 1_454 ? C5 C6 O4 Dy1 165.2(6) . . . 1_454 ? O6 N1 O5 Dy1 4.7(8) . . . . ? O7 N1 O5 Dy1 -174.8(7) . . . . ? O2 Dy1 O5 N1 163.9(5) 4_566 . . . ? O1 Dy1 O5 N1 -147.6(5) . . . . ? O4 Dy1 O5 N1 65.9(5) 1_656 . . . ? O3 Dy1 O5 N1 -72.7(5) 3_656 . . . ? O6 Dy1 O5 N1 -1.1(5) 3_757 . . . ? O8 Dy1 O5 N1 135.7(5) . . . . ? O6 Dy1 O5 N1 -2.6(4) . . . . ? Dy1 Dy1 O5 N1 -1.9(4) 3_757 . . . ? O5 N1 O6 Dy1 -173.4(11) . . . 3_757 ? O7 N1 O6 Dy1 6(2) . . . 3_757 ? Dy1 N1 O6 Dy1 -168.8(17) . . . 3_757 ? O5 N1 O6 Dy1 -4.6(7) . . . . ? O7 N1 O6 Dy1 174.9(7) . . . . ? O2 Dy1 O6 N1 -165.5(5) 4_566 . . . ? O1 Dy1 O6 N1 43.7(5) . . . . ? O4 Dy1 O6 N1 -99.9(5) 1_656 . . . ? O3 Dy1 O6 N1 106.7(5) 3_656 . . . ? O6 Dy1 O6 N1 -176.0(6) 3_757 . . . ? O8 Dy1 O6 N1 -45.6(5) . . . . ? O5 Dy1 O6 N1 2.7(4) . . . . ? Dy1 Dy1 O6 N1 -176.0(6) 3_757 . . . ? O2 Dy1 O6 Dy1 10.5(5) 4_566 . . 3_757 ? O1 Dy1 O6 Dy1 -140.3(2) . . . 3_757 ? O4 Dy1 O6 Dy1 76.1(3) 1_656 . . 3_757 ? O3 Dy1 O6 Dy1 -77.3(3) 3_656 . . 3_757 ? O6 Dy1 O6 Dy1 0.0 3_757 . . 3_757 ? O8 Dy1 O6 Dy1 130.4(2) . . . 3_757 ? O5 Dy1 O6 Dy1 178.7(4) . . . 3_757 ? N1 Dy1 O6 Dy1 176.0(6) . . . 3_757 ? C4 C5 S1 C2 -0.5(7) . . . . ? C6 C5 S1 C2 177.3(7) . . . . ? C3 C2 S1 C5 -0.6(7) . . . . ? C1 C2 S1 C5 179.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.186 _refine_diff_density_min -1.299 _refine_diff_density_rms 0.226 data_8 _database_code_depnum_ccdc_archive 'CCDC 798446' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Ho N O8 S' _chemical_formula_weight 415.09 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' Ho Ho -0.2175 4.6783 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.8814(11) _cell_length_b 14.1582(16) _cell_length_c 7.8854(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.119(3) _cell_angle_gamma 90.00 _cell_volume 1069.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1886 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 25.01 _exptl_crystal_description bolck _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 7.621 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3110 _exptl_absorpt_correction_T_max 0.3110 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6071 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1886 _reflns_number_gt 1676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XSCANS' _computing_publication_material 'Bruker XSCANS' _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^)+(0.0329P)^2^+5.8382P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0 _refine_ls_number_reflns 1886 _refine_ls_number_parameters 154 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.155 _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 0.7018(7) 0.2390(5) 0.5577(10) 0.0167(15) Uani 1 1 d . . . C2 C 0.5603(7) 0.2287(4) 0.4427(10) 0.0160(15) Uani 1 1 d . . . C3 C 0.4757(8) 0.2962(5) 0.3503(11) 0.0247(18) Uani 1 1 d . . . H3 H 0.5013 0.3593 0.3473 0.030 Uiso 1 1 calc R . . C4 C 0.3453(8) 0.2605(5) 0.2595(11) 0.029(2) Uani 1 1 d . . . H4 H 0.2744 0.2978 0.1930 0.035 Uiso 1 1 calc R . . C5 C 0.3336(7) 0.1651(5) 0.2795(10) 0.0209(16) Uani 1 1 d . . . C6 C 0.2161(8) 0.1044(5) 0.1980(12) 0.0247(17) Uani 1 1 d . . . Ho1 Ho 0.90633(3) 0.11342(2) 0.89688(4) 0.01291(11) Uani 1 1 d . . . N1 N 1.1099(8) 0.0322(5) 0.7412(10) 0.0340(18) Uani 1 1 d . . . O1 O 0.7498(5) 0.1711(3) 0.6562(7) 0.0210(11) Uani 1 1 d . . . O2 O 0.7661(5) 0.3157(3) 0.5496(7) 0.0202(11) Uani 1 1 d . . . O3 O 0.2280(5) 0.0165(3) 0.2183(8) 0.0273(13) Uani 1 1 d . . . O4 O 0.1093(5) 0.1466(4) 0.1036(8) 0.0338(15) Uani 1 1 d . . . O5 O 1.0397(5) 0.1048(3) 0.6777(7) 0.0230(12) Uani 1 1 d . . . O6 O 1.0784(5) -0.0087(3) 0.8712(7) 0.0260(13) Uani 1 1 d . . . O7 O 1.2271(9) -0.0055(6) 0.6676(14) 0.084(3) Uani 1 1 d . . . O8 O 0.9657(6) 0.2752(3) 0.8819(7) 0.0275(13) Uani 1 1 d . . . H8A H 1.0327 0.2908 0.8377 0.041 Uiso 1 1 d R . . H8B H 0.9201 0.3174 0.9209 0.041 Uiso 1 1 d R . . S1 S 0.48170(18) 0.11898(12) 0.4157(3) 0.0209(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.011(3) 0.021(3) 0.017(4) 0.000(3) 0.001(3) -0.001(3) C2 0.014(3) 0.015(3) 0.017(4) 0.002(3) -0.001(3) -0.002(3) C3 0.021(4) 0.013(3) 0.032(5) 0.006(3) -0.008(3) -0.004(3) C4 0.016(4) 0.022(4) 0.038(6) 0.008(4) -0.016(3) 0.003(3) C5 0.013(4) 0.019(3) 0.026(5) 0.003(3) -0.004(3) 0.002(3) C6 0.016(4) 0.019(3) 0.034(5) -0.001(3) -0.004(3) -0.003(3) Ho1 0.01016(16) 0.01162(15) 0.01426(19) 0.00011(14) -0.00221(12) 0.00089(13) N1 0.038(4) 0.029(4) 0.036(5) -0.004(3) 0.011(4) -0.001(3) O1 0.019(3) 0.015(2) 0.021(3) 0.008(2) -0.010(2) 0.000(2) O2 0.014(2) 0.016(2) 0.027(3) -0.001(2) -0.002(2) -0.0069(19) O3 0.025(3) 0.013(2) 0.033(4) 0.002(2) -0.014(2) -0.003(2) O4 0.020(3) 0.019(3) 0.046(4) 0.005(3) -0.023(3) 0.003(2) O5 0.026(3) 0.022(3) 0.022(3) 0.009(2) 0.006(2) 0.012(2) O6 0.028(3) 0.029(3) 0.026(4) 0.013(2) 0.017(3) 0.011(2) O7 0.068(6) 0.082(6) 0.120(9) -0.005(6) 0.057(6) 0.013(5) O8 0.034(3) 0.020(3) 0.026(4) 0.003(2) 0.004(3) -0.001(2) S1 0.0159(9) 0.0136(8) 0.0275(12) 0.0032(8) -0.0058(8) -0.0021(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.254(8) . ? C1 O2 1.267(8) . ? C1 C2 1.476(10) . ? C2 C3 1.360(10) . ? C2 S1 1.726(6) . ? C3 C4 1.407(10) . ? C3 H3 0.9300 . ? C4 C5 1.368(10) . ? C4 H4 0.9300 . ? C5 C6 1.461(10) . ? C5 S1 1.719(7) . ? C6 O3 1.257(8) . ? C6 O4 1.281(9) . ? Ho1 O2 2.279(5) 4_566 ? Ho1 O1 2.287(5) . ? Ho1 O4 2.303(5) 1_656 ? Ho1 O3 2.320(5) 3_656 ? Ho1 O6 2.330(5) 3_757 ? Ho1 O8 2.374(5) . ? Ho1 O5 2.418(5) . ? Ho1 O6 2.468(5) . ? Ho1 Ho1 3.8623(6) 3_757 ? N1 O5 1.273(8) . ? N1 O6 1.280(8) . ? N1 O7 1.514(9) . ? O2 Ho1 2.279(5) 4_565 ? O3 Ho1 2.320(5) 3_656 ? O4 Ho1 2.303(5) 1_454 ? O6 Ho1 2.330(5) 3_757 ? O8 H8A 0.8500 . ? O8 H8B 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 124.7(6) . . ? O1 C1 C2 117.6(6) . . ? O2 C1 C2 117.7(6) . . ? C3 C2 C1 128.7(6) . . ? C3 C2 S1 111.6(5) . . ? C1 C2 S1 119.7(5) . . ? C2 C3 C4 112.7(6) . . ? C2 C3 H3 123.6 . . ? C4 C3 H3 123.6 . . ? C5 C4 C3 112.9(6) . . ? C5 C4 H4 123.5 . . ? C3 C4 H4 123.5 . . ? C4 C5 C6 127.6(7) . . ? C4 C5 S1 111.3(5) . . ? C6 C5 S1 121.1(5) . . ? O3 C6 O4 125.0(7) . . ? O3 C6 C5 119.1(7) . . ? O4 C6 C5 115.8(6) . . ? O2 Ho1 O1 84.60(18) 4_566 . ? O2 Ho1 O4 94.2(2) 4_566 1_656 ? O1 Ho1 O4 144.12(18) . 1_656 ? O2 Ho1 O3 101.11(19) 4_566 3_656 ? O1 Ho1 O3 75.64(17) . 3_656 ? O4 Ho1 O3 139.03(18) 1_656 3_656 ? O2 Ho1 O6 78.28(17) 4_566 3_757 ? O1 Ho1 O6 141.25(18) . 3_757 ? O4 Ho1 O6 72.3(2) 1_656 3_757 ? O3 Ho1 O6 74.0(2) 3_656 3_757 ? O2 Ho1 O8 77.92(18) 4_566 . ? O1 Ho1 O8 74.89(18) . . ? O4 Ho1 O8 69.84(18) 1_656 . ? O3 Ho1 O8 150.47(18) 3_656 . ? O6 Ho1 O8 133.09(19) 3_757 . ? O2 Ho1 O5 155.14(16) 4_566 . ? O1 Ho1 O5 78.52(18) . . ? O4 Ho1 O5 89.1(2) 1_656 . ? O3 Ho1 O5 92.29(19) 3_656 . ? O6 Ho1 O5 125.91(16) 3_757 . ? O8 Ho1 O5 80.13(18) . . ? O2 Ho1 O6 150.70(17) 4_566 . ? O1 Ho1 O6 121.48(18) . . ? O4 Ho1 O6 72.70(19) 1_656 . ? O3 Ho1 O6 75.65(18) 3_656 . ? O6 Ho1 O6 72.82(19) 3_757 . ? O8 Ho1 O6 119.23(18) . . ? O5 Ho1 O6 53.11(16) . . ? O2 Ho1 Ho1 115.76(12) 4_566 3_757 ? O1 Ho1 Ho1 143.54(12) . 3_757 ? O4 Ho1 Ho1 68.07(13) 1_656 3_757 ? O3 Ho1 Ho1 71.04(12) 3_656 3_757 ? O6 Ho1 Ho1 37.62(12) 3_757 3_757 ? O8 Ho1 Ho1 136.40(13) . 3_757 ? O5 Ho1 Ho1 88.30(11) . 3_757 ? O6 Ho1 Ho1 35.20(12) . 3_757 ? O5 N1 O6 117.7(6) . . ? O5 N1 O7 121.9(7) . . ? O6 N1 O7 120.4(7) . . ? C1 O1 Ho1 149.9(5) . . ? C1 O2 Ho1 141.4(5) . 4_565 ? C6 O3 Ho1 135.1(5) . 3_656 ? C6 O4 Ho1 140.2(5) . 1_454 ? N1 O5 Ho1 95.7(4) . . ? N1 O6 Ho1 159.1(5) . 3_757 ? N1 O6 Ho1 93.2(4) . . ? Ho1 O6 Ho1 107.18(19) 3_757 . ? Ho1 O8 H8A 119.9 . . ? Ho1 O8 H8B 120.1 . . ? H8A O8 H8B 120.0 . . ? C5 S1 C2 91.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 166.4(8) . . . . ? O2 C1 C2 C3 -13.8(12) . . . . ? O1 C1 C2 S1 -12.5(9) . . . . ? O2 C1 C2 S1 167.2(5) . . . . ? C1 C2 C3 C4 -177.8(7) . . . . ? S1 C2 C3 C4 1.3(10) . . . . ? C2 C3 C4 C5 -2.0(11) . . . . ? C3 C4 C5 C6 -177.0(8) . . . . ? C3 C4 C5 S1 1.8(10) . . . . ? C4 C5 C6 O3 173.5(8) . . . . ? S1 C5 C6 O3 -5.1(11) . . . . ? C4 C5 C6 O4 -3.6(13) . . . . ? S1 C5 C6 O4 177.7(6) . . . . ? O2 C1 O1 Ho1 19.0(15) . . . . ? C2 C1 O1 Ho1 -161.3(6) . . . . ? O2 Ho1 O1 C1 76.5(10) 4_566 . . . ? O4 Ho1 O1 C1 -13.1(11) 1_656 . . . ? O3 Ho1 O1 C1 179.5(10) 3_656 . . . ? O6 Ho1 O1 C1 140.2(9) 3_757 . . . ? O8 Ho1 O1 C1 -2.4(9) . . . . ? O5 Ho1 O1 C1 -85.1(10) . . . . ? O6 Ho1 O1 C1 -117.7(9) . . . . ? Ho1 Ho1 O1 C1 -156.1(8) 3_757 . . . ? O1 C1 O2 Ho1 93.7(10) . . . 4_565 ? C2 C1 O2 Ho1 -86.1(8) . . . 4_565 ? O4 C6 O3 Ho1 4.6(14) . . . 3_656 ? C5 C6 O3 Ho1 -172.3(5) . . . 3_656 ? O3 C6 O4 Ho1 -11.5(15) . . . 1_454 ? C5 C6 O4 Ho1 165.4(6) . . . 1_454 ? O6 N1 O5 Ho1 5.5(7) . . . . ? O7 N1 O5 Ho1 -174.4(7) . . . . ? O2 Ho1 O5 N1 163.7(4) 4_566 . . . ? O1 Ho1 O5 N1 -148.1(4) . . . . ? O4 Ho1 O5 N1 65.8(4) 1_656 . . . ? O3 Ho1 O5 N1 -73.3(4) 3_656 . . . ? O6 Ho1 O5 N1 -1.5(5) 3_757 . . . ? O8 Ho1 O5 N1 135.4(5) . . . . ? O6 Ho1 O5 N1 -3.2(4) . . . . ? Ho1 Ho1 O5 N1 -2.3(4) 3_757 . . . ? O5 N1 O6 Ho1 -173.0(10) . . . 3_757 ? O7 N1 O6 Ho1 6.9(19) . . . 3_757 ? O5 N1 O6 Ho1 -5.4(7) . . . . ? O7 N1 O6 Ho1 174.5(7) . . . . ? O2 Ho1 O6 N1 -165.6(4) 4_566 . . . ? O1 Ho1 O6 N1 44.4(5) . . . . ? O4 Ho1 O6 N1 -99.1(5) 1_656 . . . ? O3 Ho1 O6 N1 107.2(5) 3_656 . . . ? O6 Ho1 O6 N1 -175.4(6) 3_757 . . . ? O8 Ho1 O6 N1 -45.1(5) . . . . ? O5 Ho1 O6 N1 3.1(4) . . . . ? Ho1 Ho1 O6 N1 -175.4(6) 3_757 . . . ? O2 Ho1 O6 Ho1 9.8(5) 4_566 . . 3_757 ? O1 Ho1 O6 Ho1 -140.2(2) . . . 3_757 ? O4 Ho1 O6 Ho1 76.3(2) 1_656 . . 3_757 ? O3 Ho1 O6 Ho1 -77.3(2) 3_656 . . 3_757 ? O6 Ho1 O6 Ho1 0.0 3_757 . . 3_757 ? O8 Ho1 O6 Ho1 130.3(2) . . . 3_757 ? O5 Ho1 O6 Ho1 178.6(3) . . . 3_757 ? C4 C5 S1 C2 -0.9(7) . . . . ? C6 C5 S1 C2 178.0(7) . . . . ? C3 C2 S1 C5 -0.2(6) . . . . ? C1 C2 S1 C5 178.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.104 _refine_diff_density_min -1.923 _refine_diff_density_rms 0.220 data_9 _database_code_depnum_ccdc_archive 'CCDC 798447' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Er N O8 S' _chemical_formula_weight 417.42 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' Er Er -0.2586 4.9576 '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' _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 9.8814(16) _cell_length_b 14.1582(9) _cell_length_c 7.885 _cell_angle_alpha 90.00 _cell_angle_beta 104.12 _cell_angle_gamma 90.00 _cell_volume 1069.86(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1888 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 25.02 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 8.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2476 _exptl_absorpt_correction_T_max 0.2952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method 0 _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5978 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1888 _reflns_number_gt 1606 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XSCANS' _computing_publication_material 'Bruker XSCANS' _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^)+(0.0283P)^2^+10.4269P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1888 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 0.7032(6) 0.2388(5) 0.5591(8) 0.0151(16) Uani 1 1 d . . . C2 C 0.5600(7) 0.2288(5) 0.4426(9) 0.0223(18) Uani 1 1 d . . . C3 C 0.4761(7) 0.2966(5) 0.3496(10) 0.025(2) Uani 1 1 d . . . H3 H 0.5020 0.3596 0.3459 0.030 Uiso 1 1 calc R . . C4 C 0.3447(7) 0.2602(5) 0.2589(10) 0.027(2) Uani 1 1 d . . . H4 H 0.2732 0.2971 0.1924 0.032 Uiso 1 1 calc R . . C5 C 0.3350(7) 0.1641(5) 0.2804(9) 0.0215(18) Uani 1 1 d . . . C6 C 0.2155(8) 0.1043(5) 0.1974(10) 0.0254(18) Uani 1 1 d . . . Er1 Er 0.90678(3) 0.11355(2) 0.89702(4) 0.01421(7) Uani 1 1 d . . . N1 N 1.1083(7) 0.0333(5) 0.7421(9) 0.0373(19) Uani 1 1 d . . . O1 O 0.7504(5) 0.1711(3) 0.6574(6) 0.0216(13) Uani 1 1 d . . . O2 O 0.7674(5) 0.3154(3) 0.5496(6) 0.0210(12) Uani 1 1 d . . . O3 O 0.2271(5) 0.0154(3) 0.2194(7) 0.0284(14) Uani 1 1 d . . . O4 O 0.1095(5) 0.1469(3) 0.1036(7) 0.0337(15) Uani 1 1 d . . . O5 O 1.0397(5) 0.1060(3) 0.6799(6) 0.0273(13) Uani 1 1 d . . . O6 O 1.0780(5) -0.0082(3) 0.8705(6) 0.0258(13) Uani 1 1 d . . . O7 O 1.2264(8) -0.0060(6) 0.6680(11) 0.088(3) Uani 1 1 d . . . O8 O 0.9659(5) 0.2753(3) 0.8827(6) 0.0271(13) Uani 1 1 d . . . H8A H 1.0329 0.2910 0.8384 0.041 Uiso 1 1 d R . . H8B H 0.9202 0.3175 0.9217 0.041 Uiso 1 1 d R . . S1 S 0.48214(18) 0.11864(12) 0.4161(2) 0.0221(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.013(3) 0.028(4) 0.003(3) -0.004(3) -0.002(3) -0.002(3) C2 0.026(4) 0.018(3) 0.023(4) 0.000(3) 0.006(3) 0.001(3) C3 0.023(4) 0.012(3) 0.035(4) 0.003(3) -0.006(3) -0.002(3) C4 0.015(4) 0.026(4) 0.031(4) 0.008(3) -0.008(3) 0.003(3) C5 0.015(3) 0.022(3) 0.021(4) -0.002(3) -0.007(3) 0.001(3) C6 0.034(4) 0.018(3) 0.026(4) -0.002(3) 0.011(3) -0.001(4) Er1 0.01308(13) 0.01372(13) 0.01478(13) 0.00027(15) 0.00135(10) 0.00115(15) N1 0.037(4) 0.038(4) 0.038(4) -0.007(3) 0.011(3) -0.002(3) O1 0.014(2) 0.019(2) 0.027(3) 0.007(2) -0.004(2) 0.002(2) O2 0.020(2) 0.017(2) 0.025(3) -0.004(2) 0.004(2) -0.009(2) O3 0.026(3) 0.015(2) 0.035(3) 0.002(2) -0.011(2) -0.001(2) O4 0.021(3) 0.021(2) 0.047(3) 0.006(3) -0.017(3) 0.000(2) O5 0.032(3) 0.022(2) 0.030(3) 0.013(2) 0.011(2) 0.017(2) O6 0.032(3) 0.031(3) 0.019(2) 0.014(2) 0.017(2) 0.014(2) O7 0.081(5) 0.094(6) 0.105(6) -0.010(5) 0.055(5) 0.015(5) O8 0.034(3) 0.021(3) 0.025(3) 0.002(2) 0.004(2) -0.004(2) S1 0.0197(8) 0.0139(8) 0.0285(9) 0.0017(8) -0.0021(7) -0.0029(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.249(8) . ? C1 O2 1.269(8) . ? C1 C2 1.494(9) . ? C2 C3 1.360(9) . ? C2 S1 1.730(7) . ? C3 C4 1.418(9) . ? C3 H3 0.9300 . ? C4 C5 1.378(10) . ? C4 H4 0.9300 . ? C5 C6 1.470(10) . ? C5 S1 1.707(7) . ? C6 O3 1.272(8) . ? C6 O4 1.277(8) . ? Er1 O2 2.272(5) 4_566 ? Er1 O1 2.280(4) . ? Er1 O4 2.302(5) 1_656 ? Er1 O3 2.309(5) 3_656 ? Er1 O6 2.340(5) 3_757 ? Er1 O8 2.373(5) . ? Er1 O5 2.401(5) . ? Er1 O6 2.459(5) . ? Er1 Er1 3.8614(6) 3_757 ? N1 O5 1.264(8) . ? N1 O6 1.268(8) . ? N1 O7 1.532(10) . ? O2 Er1 2.272(5) 4_565 ? O3 Er1 2.309(5) 3_656 ? O4 Er1 2.302(5) 1_454 ? O6 Er1 2.340(5) 3_757 ? O8 H8A 0.8500 . ? O8 H8B 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 125.2(6) . . ? O1 C1 C2 117.6(6) . . ? O2 C1 C2 117.2(6) . . ? C3 C2 C1 128.8(6) . . ? C3 C2 S1 112.1(5) . . ? C1 C2 S1 119.1(5) . . ? C2 C3 C4 112.2(6) . . ? C2 C3 H3 123.9 . . ? C4 C3 H3 123.9 . . ? C5 C4 C3 112.3(6) . . ? C5 C4 H4 123.9 . . ? C3 C4 H4 123.9 . . ? C4 C5 C6 125.9(6) . . ? C4 C5 S1 112.0(5) . . ? C6 C5 S1 122.1(5) . . ? O3 C6 O4 125.5(7) . . ? O3 C6 C5 118.2(6) . . ? O4 C6 C5 116.3(6) . . ? O2 Er1 O1 84.54(17) 4_566 . ? O2 Er1 O4 94.00(18) 4_566 1_656 ? O1 Er1 O4 144.11(17) . 1_656 ? O2 Er1 O3 101.41(18) 4_566 3_656 ? O1 Er1 O3 75.31(16) . 3_656 ? O4 Er1 O3 139.36(17) 1_656 3_656 ? O2 Er1 O6 78.39(17) 4_566 3_757 ? O1 Er1 O6 141.11(17) . 3_757 ? O4 Er1 O6 72.40(18) 1_656 3_757 ? O3 Er1 O6 74.25(17) 3_656 3_757 ? O2 Er1 O8 77.65(18) 4_566 . ? O1 Er1 O8 74.95(16) . . ? O4 Er1 O8 69.76(17) 1_656 . ? O3 Er1 O8 150.19(16) 3_656 . ? O6 Er1 O8 133.10(16) 3_757 . ? O2 Er1 O5 154.79(16) 4_566 . ? O1 Er1 O5 78.63(17) . . ? O4 Er1 O5 88.90(19) 1_656 . ? O3 Er1 O5 92.38(18) 3_656 . ? O6 Er1 O5 126.06(16) 3_757 . ? O8 Er1 O5 79.92(17) . . ? O2 Er1 O6 150.86(16) 4_566 . ? O1 Er1 O6 121.42(16) . . ? O4 Er1 O6 72.90(17) 1_656 . ? O3 Er1 O6 75.62(17) 3_656 . ? O6 Er1 O6 72.88(19) 3_757 . ? O8 Er1 O6 119.34(17) . . ? O5 Er1 O6 53.21(15) . . ? O2 Er1 Er1 115.74(11) 4_566 3_757 ? O1 Er1 Er1 143.48(12) . 3_757 ? O4 Er1 Er1 68.26(12) 1_656 3_757 ? O3 Er1 Er1 71.17(11) 3_656 3_757 ? O6 Er1 Er1 37.50(12) 3_757 3_757 ? O8 Er1 Er1 136.55(12) . 3_757 ? O5 Er1 Er1 88.58(11) . 3_757 ? O6 Er1 Er1 35.39(11) . 3_757 ? O5 N1 O6 118.6(6) . . ? O5 N1 O7 122.3(7) . . ? O6 N1 O7 119.1(6) . . ? C1 O1 Er1 149.7(4) . . ? C1 O2 Er1 141.8(4) . 4_565 ? C6 O3 Er1 134.8(4) . 3_656 ? C6 O4 Er1 139.7(5) . 1_454 ? N1 O5 Er1 95.4(4) . . ? N1 O6 Er1 159.8(5) . 3_757 ? N1 O6 Er1 92.6(4) . . ? Er1 O6 Er1 107.12(19) 3_757 . ? Er1 O8 H8A 119.8 . . ? Er1 O8 H8B 120.2 . . ? H8A O8 H8B 120.0 . . ? C5 S1 C2 91.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 166.6(8) . . . . ? O2 C1 C2 C3 -13.6(11) . . . . ? O1 C1 C2 S1 -13.0(9) . . . . ? O2 C1 C2 S1 166.8(5) . . . . ? C1 C2 C3 C4 -177.9(7) . . . . ? S1 C2 C3 C4 1.8(9) . . . . ? C2 C3 C4 C5 -2.5(10) . . . . ? C3 C4 C5 C6 -177.0(7) . . . . ? C3 C4 C5 S1 2.1(9) . . . . ? C4 C5 C6 O3 174.4(8) . . . . ? S1 C5 C6 O3 -4.6(10) . . . . ? C4 C5 C6 O4 -3.4(12) . . . . ? S1 C5 C6 O4 177.6(6) . . . . ? O2 C1 O1 Er1 18.5(14) . . . . ? C2 C1 O1 Er1 -161.8(6) . . . . ? O2 Er1 O1 C1 77.2(9) 4_566 . . . ? O4 Er1 O1 C1 -12.1(11) 1_656 . . . ? O3 Er1 O1 C1 -179.5(9) 3_656 . . . ? O6 Er1 O1 C1 141.0(8) 3_757 . . . ? O8 Er1 O1 C1 -1.5(9) . . . . ? O5 Er1 O1 C1 -84.0(9) . . . . ? O6 Er1 O1 C1 -116.9(9) . . . . ? Er1 Er1 O1 C1 -155.7(8) 3_757 . . . ? O1 C1 O2 Er1 93.7(8) . . . 4_565 ? C2 C1 O2 Er1 -86.1(8) . . . 4_565 ? O4 C6 O3 Er1 6.0(13) . . . 3_656 ? C5 C6 O3 Er1 -171.6(5) . . . 3_656 ? O3 C6 O4 Er1 -12.2(14) . . . 1_454 ? C5 C6 O4 Er1 165.5(5) . . . 1_454 ? O6 N1 O5 Er1 5.1(6) . . . . ? O7 N1 O5 Er1 -174.8(6) . . . . ? O2 Er1 O5 N1 163.5(4) 4_566 . . . ? O1 Er1 O5 N1 -147.4(4) . . . . ? O4 Er1 O5 N1 66.4(4) 1_656 . . . ? O3 Er1 O5 N1 -72.9(4) 3_656 . . . ? O6 Er1 O5 N1 -0.7(5) 3_757 . . . ? O8 Er1 O5 N1 136.1(4) . . . . ? O6 Er1 O5 N1 -2.9(4) . . . . ? Er1 Er1 O5 N1 -1.8(4) 3_757 . . . ? O5 N1 O6 Er1 -171.9(9) . . . 3_757 ? O7 N1 O6 Er1 8.1(17) . . . 3_757 ? O5 N1 O6 Er1 -5.0(6) . . . . ? O7 N1 O6 Er1 175.0(5) . . . . ? O2 Er1 O6 N1 -165.3(4) 4_566 . . . ? O1 Er1 O6 N1 44.7(4) . . . . ? O4 Er1 O6 N1 -99.0(4) 1_656 . . . ? O3 Er1 O6 N1 107.1(4) 3_656 . . . ? O6 Er1 O6 N1 -175.3(5) 3_757 . . . ? O8 Er1 O6 N1 -45.0(4) . . . . ? O5 Er1 O6 N1 2.9(4) . . . . ? Er1 Er1 O6 N1 -175.3(5) 3_757 . . . ? O2 Er1 O6 Er1 10.0(4) 4_566 . . 3_757 ? O1 Er1 O6 Er1 -140.02(18) . . . 3_757 ? O4 Er1 O6 Er1 76.3(2) 1_656 . . 3_757 ? O3 Er1 O6 Er1 -77.6(2) 3_656 . . 3_757 ? O6 Er1 O6 Er1 0.0 3_757 . . 3_757 ? O8 Er1 O6 Er1 130.31(18) . . . 3_757 ? O5 Er1 O6 Er1 178.2(3) . . . 3_757 ? C4 C5 S1 C2 -0.9(6) . . . . ? C6 C5 S1 C2 178.2(7) . . . . ? C3 C2 S1 C5 -0.5(6) . . . . ? C1 C2 S1 C5 179.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.057 _refine_diff_density_min -1.422 _refine_diff_density_rms 0.205 data_10 _database_code_depnum_ccdc_archive 'CCDC 798448' #TrackingRef '- Crystal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 N O8 S Yb' _chemical_formula_weight 423.20 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' Yb Yb -0.3850 5.5486 '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 9.8814(16) _cell_length_b 14.1582(9) _cell_length_c 7.885 _cell_angle_alpha 90.00 _cell_angle_beta 104.12 _cell_angle_gamma 90.00 _cell_volume 1069.86(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1887 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 25.02 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 8.967 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.1739 _exptl_absorpt_correction_T_max 0.2672 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7501 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1887 _reflns_number_gt 1563 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0508P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1887 _refine_ls_number_parameters 154 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0821 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.139 _refine_ls_shift/su_mean 0.013 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 0.7024(3) 0.23992(19) 0.5585(4) 0.0086(7) Uani 1 1 d . . . C2 C 0.5621(3) 0.22944(18) 0.4398(4) 0.0082(7) Uani 1 1 d . . . C3 C 0.4764(3) 0.29851(19) 0.3474(4) 0.0135(8) Uani 1 1 d . . . H3 H 0.5014 0.3619 0.3475 0.016 Uiso 1 1 calc R . . C4 C 0.3454(3) 0.2622(2) 0.2516(4) 0.0160(8) Uani 1 1 d . . . H4 H 0.2741 0.2989 0.1846 0.019 Uiso 1 1 calc R . . C5 C 0.3377(2) 0.1660(2) 0.2710(4) 0.0091(7) Uani 1 1 d . . . C6 C 0.2181(3) 0.10377(18) 0.1819(4) 0.0090(3) Uani 1 1 d U . . N1 N 1.1054(3) 0.03186(19) 0.7340(4) 0.0289(9) Uani 1 1 d . . . O1 O 0.74848(18) 0.17056(13) 0.6549(2) 0.0111(5) Uani 1 1 d . . . O2 O 0.76638(18) 0.31808(12) 0.5566(3) 0.0106(5) Uani 1 1 d . . . O3 O 0.23147(19) 0.01534(12) 0.2091(3) 0.0139(6) Uani 1 1 d . . . O4 O 0.11547(18) 0.14656(15) 0.0851(3) 0.0160(6) Uani 1 1 d . . . O5 O 1.03605(19) 0.10459(12) 0.6702(3) 0.0105(5) Uani 1 1 d . . . O6 O 1.06892(18) -0.01394(13) 0.8602(3) 0.0131(5) Uani 1 1 d . . . O7 O 1.2270(3) -0.0044(2) 0.6618(4) 0.0582(10) Uani 1 1 d . . . O8 O 0.96027(19) 0.27333(13) 0.8794(3) 0.0132(5) Uani 1 1 d . . . H8A H 1.0273 0.2890 0.8352 0.020 Uiso 1 1 d R . . H8B H 0.9146 0.3155 0.9184 0.020 Uiso 1 1 d R . . S1 S 0.48353(7) 0.11879(5) 0.40993(10) 0.01041(19) Uani 1 1 d . . . Yb1 Yb 0.906921(11) 0.112895(7) 0.896113(15) 0.00577(3) 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 C1 0.0066(11) 0.0110(13) 0.0097(14) 0.0036(11) 0.0048(9) 0.0020(10) C2 0.0104(12) 0.0085(13) 0.0061(14) 0.0031(11) 0.0028(10) -0.0027(10) C3 0.0112(13) 0.0081(13) 0.0193(16) 0.0049(12) 0.0002(11) 0.0003(11) C4 0.0115(13) 0.0109(14) 0.0227(17) 0.0038(13) -0.0013(12) -0.0007(11) C5 0.0038(11) 0.0123(13) 0.0118(14) 0.0012(12) 0.0034(9) -0.0002(11) C6 0.0088(5) 0.0091(5) 0.0085(5) 0.0002(4) 0.0008(4) -0.0008(4) N1 0.0290(14) 0.0255(15) 0.0315(17) -0.0097(13) 0.0064(12) -0.0055(12) O1 0.0114(8) 0.0092(9) 0.0100(10) 0.0003(9) -0.0030(7) 0.0012(8) O2 0.0064(8) 0.0098(9) 0.0133(10) 0.0009(8) -0.0018(7) -0.0048(7) O3 0.0133(9) 0.0066(9) 0.0173(11) 0.0022(9) -0.0050(8) -0.0024(8) O4 0.0100(9) 0.0108(10) 0.0207(12) 0.0032(9) -0.0089(8) -0.0004(8) O5 0.0112(9) 0.0118(10) 0.0098(10) 0.0097(8) 0.0052(7) 0.0068(7) O6 0.0182(9) 0.0141(9) 0.0120(10) 0.0061(8) 0.0131(7) 0.0069(8) O7 0.0527(14) 0.0573(18) 0.078(2) 0.0012(15) 0.0422(13) 0.0107(14) O8 0.0151(9) 0.0091(9) 0.0159(11) 0.0001(9) 0.0050(7) 0.0007(8) S1 0.0076(3) 0.0086(3) 0.0123(4) 0.0015(3) -0.0030(3) -0.0015(2) Yb1 0.00565(6) 0.00564(6) 0.00535(6) 0.00024(5) 0.00005(4) 0.00029(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 O1 1.257(3) . ? C1 O2 1.276(3) . ? C1 C2 1.479(3) . ? C2 C3 1.379(4) . ? C2 S1 1.739(3) . ? C3 C4 1.426(4) . ? C3 H3 0.9300 . ? C4 C5 1.374(4) . ? C4 H4 0.9300 . ? C5 C6 1.504(4) . ? C5 S1 1.719(2) . ? C6 O4 1.265(3) . ? C6 O3 1.272(3) . ? N1 O5 1.271(3) . ? N1 O6 1.310(4) . ? N1 O7 1.538(4) . ? O1 Yb1 2.2984(17) . ? O2 Yb1 2.311(2) 4_565 ? O3 Yb1 2.3024(18) 3_656 ? O4 Yb1 2.2794(17) 1_454 ? O5 Yb1 2.434(2) . ? O6 Yb1 2.3426(19) 3_757 ? O6 Yb1 2.4674(19) . ? O8 Yb1 2.3428(18) . ? O8 H8A 0.8500 . ? O8 H8B 0.8500 . ? Yb1 O4 2.2794(17) 1_656 ? Yb1 O3 2.3024(18) 3_656 ? Yb1 O2 2.311(2) 4_566 ? Yb1 O6 2.343(2) 3_757 ? Yb1 Yb1 3.8493(3) 3_757 ? 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 125.2(2) . . ? O1 C1 C2 116.7(2) . . ? O2 C1 C2 118.0(2) . . ? C3 C2 C1 128.5(2) . . ? C3 C2 S1 111.78(18) . . ? C1 C2 S1 119.65(19) . . ? C2 C3 C4 112.6(2) . . ? C2 C3 H3 123.7 . . ? C4 C3 H3 123.7 . . ? C5 C4 C3 111.5(2) . . ? C5 C4 H4 124.3 . . ? C3 C4 H4 124.3 . . ? C4 C5 C6 126.0(2) . . ? C4 C5 S1 113.32(19) . . ? C6 C5 S1 120.7(2) . . ? O4 C6 O3 127.5(2) . . ? O4 C6 C5 115.1(2) . . ? O3 C6 C5 117.4(2) . . ? O5 N1 O6 118.7(3) . . ? O5 N1 O7 121.2(3) . . ? O6 N1 O7 120.0(2) . . ? C1 O1 Yb1 148.31(16) . . ? C1 O2 Yb1 137.60(19) . 4_565 ? C6 O3 Yb1 133.43(16) . 3_656 ? C6 O4 Yb1 139.30(18) . 1_454 ? N1 O5 Yb1 94.46(18) . . ? N1 O6 Yb1 158.03(16) . 3_757 ? N1 O6 Yb1 91.91(15) . . ? Yb1 O6 Yb1 106.28(8) 3_757 . ? Yb1 O8 H8A 119.0 . . ? Yb1 O8 H8B 121.0 . . ? H8A O8 H8B 120.0 . . ? C5 S1 C2 90.74(12) . . ? O4 Yb1 O1 142.31(7) 1_656 . ? O4 Yb1 O3 139.75(7) 1_656 3_656 ? O1 Yb1 O3 75.94(6) . 3_656 ? O4 Yb1 O2 97.00(7) 1_656 4_566 ? O1 Yb1 O2 85.64(7) . 4_566 ? O3 Yb1 O2 98.47(7) 3_656 4_566 ? O4 Yb1 O6 72.18(7) 1_656 3_757 ? O1 Yb1 O6 143.49(6) . 3_757 ? O3 Yb1 O6 75.91(7) 3_656 3_757 ? O2 Yb1 O6 76.02(7) 4_566 3_757 ? O4 Yb1 O8 69.76(7) 1_656 . ? O1 Yb1 O8 74.12(6) . . ? O3 Yb1 O8 150.03(6) 3_656 . ? O2 Yb1 O8 78.13(7) 4_566 . ? O6 Yb1 O8 130.29(7) 3_757 . ? O4 Yb1 O5 86.37(7) 1_656 . ? O1 Yb1 O5 77.55(7) . . ? O3 Yb1 O5 93.99(7) 3_656 . ? O2 Yb1 O5 155.98(6) 4_566 . ? O6 Yb1 O5 127.20(6) 3_757 . ? O8 Yb1 O5 80.82(7) . . ? O4 Yb1 O6 73.67(7) 1_656 . ? O1 Yb1 O6 119.58(7) . . ? O3 Yb1 O6 74.32(6) 3_656 . ? O2 Yb1 O6 149.74(7) 4_566 . ? O6 Yb1 O6 73.72(8) 3_757 . ? O8 Yb1 O6 122.55(7) . . ? O5 Yb1 O6 53.87(6) . . ? O4 Yb1 Yb1 68.50(5) 1_656 3_757 ? O1 Yb1 Yb1 143.66(5) . 3_757 ? O3 Yb1 Yb1 71.26(4) 3_656 3_757 ? O2 Yb1 Yb1 113.99(5) 4_566 3_757 ? O6 Yb1 Yb1 37.97(5) 3_757 3_757 ? O8 Yb1 Yb1 137.60(4) . 3_757 ? O5 Yb1 Yb1 89.43(4) . 3_757 ? O6 Yb1 Yb1 35.74(5) . 3_757 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 166.0(3) . . . . ? O2 C1 C2 C3 -13.4(5) . . . . ? O1 C1 C2 S1 -11.5(4) . . . . ? O2 C1 C2 S1 169.1(2) . . . . ? C1 C2 C3 C4 -177.5(3) . . . . ? S1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 -1.7(4) . . . . ? C3 C4 C5 C6 -176.7(3) . . . . ? C3 C4 C5 S1 2.4(4) . . . . ? C4 C5 C6 O4 -2.1(5) . . . . ? S1 C5 C6 O4 178.8(2) . . . . ? C4 C5 C6 O3 176.9(3) . . . . ? S1 C5 C6 O3 -2.2(4) . . . . ? O2 C1 O1 Yb1 15.9(6) . . . . ? C2 C1 O1 Yb1 -163.4(2) . . . . ? O1 C1 O2 Yb1 96.0(3) . . . 4_565 ? C2 C1 O2 Yb1 -84.6(3) . . . 4_565 ? O4 C6 O3 Yb1 1.8(5) . . . 3_656 ? C5 C6 O3 Yb1 -177.01(19) . . . 3_656 ? O3 C6 O4 Yb1 -3.7(6) . . . 1_454 ? C5 C6 O4 Yb1 175.1(2) . . . 1_454 ? O6 N1 O5 Yb1 10.4(2) . . . . ? O7 N1 O5 Yb1 -171.5(2) . . . . ? O5 N1 O6 Yb1 -156.6(3) . . . 3_757 ? O7 N1 O6 Yb1 25.3(6) . . . 3_757 ? O5 N1 O6 Yb1 -10.3(2) . . . . ? O7 N1 O6 Yb1 171.6(2) . . . . ? C4 C5 S1 C2 -1.9(3) . . . . ? C6 C5 S1 C2 177.3(3) . . . . ? C3 C2 S1 C5 0.9(2) . . . . ? C1 C2 S1 C5 178.9(2) . . . . ? C1 O1 Yb1 O4 -18.1(4) . . . 1_656 ? C1 O1 Yb1 O3 177.5(4) . . . 3_656 ? C1 O1 Yb1 O2 77.7(4) . . . 4_566 ? C1 O1 Yb1 O6 137.0(3) . . . 3_757 ? C1 O1 Yb1 O8 -1.2(4) . . . . ? C1 O1 Yb1 O5 -85.1(4) . . . . ? C1 O1 Yb1 O6 -120.0(4) . . . . ? C1 O1 Yb1 Yb1 -156.6(3) . . . 3_757 ? N1 O5 Yb1 O4 66.39(15) . . . 1_656 ? N1 O5 Yb1 O1 -147.91(15) . . . . ? N1 O5 Yb1 O3 -73.27(15) . . . 3_656 ? N1 O5 Yb1 O2 165.46(16) . . . 4_566 ? N1 O5 Yb1 O6 2.06(17) . . . 3_757 ? N1 O5 Yb1 O8 136.46(15) . . . . ? N1 O5 Yb1 O6 -5.99(14) . . . . ? N1 O5 Yb1 Yb1 -2.10(14) . . . 3_757 ? N1 O6 Yb1 O4 -91.81(15) . . . 1_656 ? Yb1 O6 Yb1 O4 75.72(8) 3_757 . . 1_656 ? N1 O6 Yb1 O1 49.63(16) . . . . ? Yb1 O6 Yb1 O1 -142.85(7) 3_757 . . . ? N1 O6 Yb1 O3 112.92(15) . . . 3_656 ? Yb1 O6 Yb1 O3 -79.55(8) 3_757 . . 3_656 ? N1 O6 Yb1 O2 -167.31(14) . . . 4_566 ? Yb1 O6 Yb1 O2 0.22(15) 3_757 . . 4_566 ? N1 O6 Yb1 O6 -167.53(17) . . . 3_757 ? Yb1 O6 Yb1 O6 0.0 3_757 . . 3_757 ? N1 O6 Yb1 O8 -39.74(16) . . . . ? Yb1 O6 Yb1 O8 127.79(7) 3_757 . . . ? N1 O6 Yb1 O5 5.80(13) . . . . ? Yb1 O6 Yb1 O5 173.33(10) 3_757 . . . ? N1 O6 Yb1 Yb1 -167.53(17) . . . 3_757 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.499 _refine_diff_density_min -1.837 _refine_diff_density_rms 0.251