# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 Gd N3 O13 S2' _chemical_formula_weight 749.82 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' Gd Gd -0.1653 3.9035 '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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.1484(14) _cell_length_b 21.509(3) _cell_length_c 25.374(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.561(2) _cell_angle_gamma 90.00 _cell_volume 5461.8(13) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3930 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 23.18 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2984 _exptl_absorpt_coefficient_mu 2.652 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4571 _exptl_absorpt_correction_T_max 0.5931 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15930 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5932 _reflns_number_gt 4518 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5932 _refine_ls_number_parameters 356 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.004 _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 Gd1 Gd 0.61247(3) 0.067118(13) 0.527699(11) 0.03496(14) Uani 1 1 d . . . S2 S 0.88083(18) 0.19115(8) 0.56028(6) 0.0470(4) Uani 1 1 d . . . S1 S 1.2211(2) 0.01570(9) 0.65820(8) 0.0583(5) Uani 1 1 d . . . N2 N 1.3453(5) 0.0724(2) 0.8687(2) 0.0354(11) Uani 1 1 d . . . C15 C 1.6372(6) 0.1725(3) 0.9562(3) 0.0456(15) Uani 1 1 d . . . H15A H 1.6562 0.1649 0.9927 0.055 Uiso 1 1 calc R . . O4 O 0.7576(4) 0.1560(2) 0.55872(17) 0.0429(10) Uani 1 1 d . . . C2 C 1.1130(8) -0.1101(4) 0.9274(4) 0.067(2) Uani 1 1 d . . . H2A H 1.0826 -0.1415 0.9475 0.080 Uiso 1 1 calc R . . O3W O 0.5204(5) 0.1344(2) 0.45581(18) 0.0596(13) Uani 1 1 d . . . H3WA H 0.4487 0.1338 0.4331 0.089 Uiso 1 1 d R . . H3WB H 0.5612 0.1680 0.4514 0.089 Uiso 1 1 d R . . N3 N 1.5333(5) 0.1436(2) 0.92776(19) 0.0367(11) Uani 1 1 d . . . N1 N 1.2272(6) -0.0121(3) 0.9241(2) 0.0471(13) Uani 1 1 d . . . O2W O 0.7988(6) 0.0709(2) 0.4787(2) 0.0750(19) Uani 1 1 d . . . H2WA H 0.8503 0.0600 0.4571 0.113 Uiso 1 1 d R . . H2WB H 0.8299 0.1042 0.4939 0.113 Uiso 1 1 d R . . O1W O 0.4350(4) 0.00641(18) 0.53839(16) 0.0410(10) Uani 1 1 d D . . H1W H 0.3976 0.0170 0.5638 0.062 Uiso 1 1 d RD . . O6 O 0.8603(6) 0.2568(2) 0.5674(2) 0.0687(16) Uani 1 1 d . . . O5 O 0.9490(5) 0.1758(3) 0.51558(19) 0.0676(15) Uani 1 1 d . . . C19 C 0.9895(6) 0.1659(3) 0.6189(2) 0.0395(14) Uani 1 1 d . . . C16 C 1.1573(6) 0.1236(3) 0.7107(2) 0.0414(14) Uani 1 1 d . . . C11 C 1.5052(6) 0.1564(3) 0.8750(2) 0.0360(13) Uani 1 1 d . . . C20 C 1.0165(7) 0.2038(3) 0.6629(2) 0.0475(15) Uani 1 1 d . . . H20A H 0.9785 0.2432 0.6622 0.057 Uiso 1 1 calc R . . C4 C 1.1328(9) -0.0651(3) 0.8439(4) 0.063(2) Uani 1 1 d . . . H4A H 1.1151 -0.0658 0.8068 0.076 Uiso 1 1 calc R . . C9 C 1.3331(6) 0.1380(3) 0.7919(2) 0.0427(14) Uani 1 1 d . . . H9A H 1.3644 0.1727 0.7759 0.051 Uiso 1 1 calc R . . C12 C 1.5786(6) 0.1972(3) 0.8511(3) 0.0423(14) Uani 1 1 d . . . H12A H 1.5565 0.2050 0.8146 0.051 Uiso 1 1 calc R . . O1 O 1.1758(7) -0.0280(2) 0.6922(2) 0.0787(17) Uani 1 1 d . . . C18 C 1.0491(7) 0.1087(3) 0.6192(2) 0.0464(16) Uani 1 1 d . . . H18A H 1.0322 0.0837 0.5890 0.056 Uiso 1 1 calc R . . C10 C 1.3892(6) 0.1216(3) 0.8440(2) 0.0360(13) Uani 1 1 d . . . C17 C 1.1343(7) 0.0876(3) 0.6641(2) 0.0413(14) Uani 1 1 d . . . C6 C 1.2482(6) 0.0377(3) 0.8411(2) 0.0407(14) Uani 1 1 d . . . C14 C 1.7191(7) 0.2135(3) 0.9342(3) 0.0523(17) Uani 1 1 d . . . H14A H 1.7938 0.2311 0.9551 0.063 Uiso 1 1 calc R . . C7 C 1.1886(7) 0.0513(3) 0.7894(3) 0.0428(15) Uani 1 1 d . . . H7A H 1.1205 0.0263 0.7718 0.051 Uiso 1 1 calc R . . O3 O 1.3618(6) 0.0295(3) 0.6739(4) 0.117(3) Uani 1 1 d . . . C21 C 1.1004(7) 0.1835(3) 0.7085(2) 0.0454(15) Uani 1 1 d . . . H21A H 1.1193 0.2097 0.7380 0.054 Uiso 1 1 calc R . . C13 C 1.6865(7) 0.2270(3) 0.8811(3) 0.0485(16) Uani 1 1 d . . . H13A H 1.7361 0.2559 0.8654 0.058 Uiso 1 1 calc R . . C5 C 1.2004(6) -0.0152(3) 0.8705(3) 0.0430(14) Uani 1 1 d . . . C1 C 1.1805(8) -0.0590(3) 0.9526(4) 0.059(2) Uani 1 1 d . . . H1A H 1.1941 -0.0566 0.9897 0.071 Uiso 1 1 calc R . . C3 C 1.0919(8) -0.1136(4) 0.8727(4) 0.072(2) Uani 1 1 d . . . H3A H 1.0505 -0.1483 0.8553 0.087 Uiso 1 1 calc R . . O2 O 1.1857(10) -0.0011(3) 0.6031(3) 0.128(3) Uani 1 1 d . . . C8 C 1.2315(6) 0.1028(3) 0.7641(2) 0.0405(14) Uani 1 1 d . . . O6W O 0.4951(12) 0.0915(6) 0.3562(4) 0.179(5) Uani 1 1 d . . . O5W O 1.6147(19) 0.3012(8) 0.7444(6) 0.328(13) Uani 1 1 d . . . O4W O 0.7055(18) 0.3195(9) 0.6393(10) 0.399(16) Uani 1 1 d . . . O7W O 0.390(3) 0.1468(15) 0.2677(14) 0.491(19) Uiso 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 Gd1 0.0406(2) 0.0328(2) 0.03085(19) -0.00246(11) 0.00403(14) -0.01152(12) S2 0.0524(10) 0.0514(10) 0.0331(8) 0.0085(7) -0.0050(7) -0.0258(8) S1 0.0706(13) 0.0547(11) 0.0517(11) -0.0083(8) 0.0169(9) -0.0023(9) N2 0.044(3) 0.031(2) 0.031(3) 0.0003(19) 0.004(2) 0.006(2) C15 0.038(3) 0.049(4) 0.046(4) -0.007(3) -0.003(3) -0.002(3) O4 0.041(2) 0.045(2) 0.040(2) 0.0002(19) -0.0013(19) -0.0174(19) C2 0.060(5) 0.050(4) 0.089(6) 0.016(4) 0.010(5) -0.013(4) O3W 0.082(4) 0.051(3) 0.043(3) 0.008(2) 0.004(3) -0.021(3) N3 0.038(3) 0.034(3) 0.035(3) 0.000(2) -0.002(2) 0.005(2) N1 0.044(3) 0.053(3) 0.045(3) 0.008(3) 0.010(3) 0.002(3) O2W 0.081(4) 0.083(4) 0.072(4) -0.033(3) 0.044(3) -0.038(3) O1W 0.051(3) 0.040(2) 0.033(2) -0.0087(17) 0.0132(19) -0.0161(19) O6 0.091(4) 0.048(3) 0.056(3) 0.012(2) -0.020(3) -0.027(3) O5 0.065(3) 0.102(4) 0.035(2) 0.005(3) 0.006(2) -0.033(3) C19 0.034(3) 0.050(4) 0.031(3) 0.009(3) -0.004(2) -0.015(3) C16 0.038(3) 0.052(4) 0.032(3) 0.000(3) -0.001(3) -0.008(3) C11 0.036(3) 0.032(3) 0.039(3) -0.005(2) 0.002(3) 0.005(2) C20 0.057(4) 0.050(4) 0.034(3) 0.002(3) 0.004(3) -0.003(3) C4 0.066(5) 0.048(4) 0.071(6) -0.001(3) 0.000(4) -0.011(3) C9 0.044(3) 0.048(4) 0.036(3) 0.001(3) 0.004(3) -0.004(3) C12 0.046(4) 0.044(3) 0.036(3) -0.002(3) 0.003(3) -0.004(3) O1 0.107(5) 0.045(3) 0.089(4) 0.000(3) 0.030(4) -0.003(3) C18 0.048(4) 0.062(4) 0.027(3) -0.006(3) 0.001(3) -0.016(3) C10 0.044(3) 0.036(3) 0.028(3) -0.002(2) 0.006(3) 0.004(3) C17 0.050(4) 0.040(3) 0.035(3) -0.001(3) 0.011(3) -0.004(3) C6 0.043(3) 0.042(3) 0.037(3) -0.002(3) 0.006(3) 0.002(3) C14 0.049(4) 0.050(4) 0.053(4) -0.020(3) -0.004(3) 0.001(3) C7 0.049(4) 0.041(3) 0.037(3) -0.006(3) 0.002(3) -0.002(3) O3 0.051(4) 0.088(5) 0.213(9) -0.005(5) 0.025(5) 0.006(3) C21 0.052(4) 0.052(4) 0.028(3) -0.007(3) -0.003(3) 0.000(3) C13 0.044(4) 0.048(4) 0.055(4) -0.007(3) 0.011(3) 0.003(3) C5 0.040(3) 0.037(3) 0.049(4) 0.008(3) 0.002(3) 0.005(3) C1 0.059(5) 0.049(4) 0.070(5) 0.015(4) 0.013(4) -0.002(3) C3 0.072(6) 0.047(4) 0.091(7) 0.009(4) -0.008(5) -0.019(4) O2 0.219(10) 0.111(6) 0.049(4) -0.025(4) 0.006(5) 0.064(6) C8 0.045(4) 0.045(3) 0.031(3) -0.003(3) 0.005(3) 0.003(3) O6W 0.178(10) 0.273(13) 0.087(7) -0.059(8) 0.026(7) -0.040(10) O5W 0.39(2) 0.34(2) 0.199(14) -0.119(15) -0.104(17) 0.218(18) O4W 0.287(18) 0.36(2) 0.64(4) 0.37(2) 0.33(2) 0.235(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 Gd1 O1W 2.277(4) . ? Gd1 O1W 2.297(4) 5_656 ? Gd1 O3W 2.393(5) . ? Gd1 O2W 2.430(5) . ? Gd1 O4 2.461(4) . ? Gd1 N1 2.527(6) 2_756 ? Gd1 N3 2.594(5) 2_756 ? Gd1 N2 2.596(5) 2_756 ? Gd1 Gd1 3.8023(6) 5_656 ? S2 O6 1.443(6) . ? S2 O4 1.457(4) . ? S2 O5 1.461(5) . ? S2 C19 1.783(6) . ? S1 O1 1.405(6) . ? S1 O2 1.431(6) . ? S1 O3 1.448(7) . ? S1 C17 1.799(7) . ? N2 C10 1.343(7) . ? N2 C6 1.338(8) . ? N2 Gd1 2.596(5) 2_756 ? C15 N3 1.329(8) . ? C15 C14 1.389(10) . ? C2 C3 1.370(12) . ? C2 C1 1.394(11) . ? N3 C11 1.351(7) . ? N3 Gd1 2.594(5) 2_756 ? N1 C5 1.344(8) . ? N1 C1 1.372(9) . ? N1 Gd1 2.527(6) 2_756 ? O1W Gd1 2.297(4) 5_656 ? C19 C18 1.369(10) . ? C19 C20 1.373(9) . ? C16 C17 1.401(8) . ? C16 C21 1.408(9) . ? C16 C8 1.504(8) . ? C11 C12 1.358(9) . ? C11 C10 1.503(8) . ? C20 C21 1.389(9) . ? C4 C3 1.378(11) . ? C4 C5 1.386(9) . ? C9 C8 1.375(8) . ? C9 C10 1.395(8) . ? C12 C13 1.384(9) . ? C18 C17 1.386(9) . ? C6 C7 1.381(8) . ? C6 C5 1.485(9) . ? C14 C13 1.364(10) . ? C7 C8 1.386(9) . ? 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 O1W Gd1 O1W 67.54(16) . 5_656 ? O1W Gd1 O3W 102.79(16) . . ? O1W Gd1 O3W 81.48(17) 5_656 . ? O1W Gd1 O2W 141.10(15) . . ? O1W Gd1 O2W 74.74(16) 5_656 . ? O3W Gd1 O2W 80.1(2) . . ? O1W Gd1 O4 148.25(14) . . ? O1W Gd1 O4 144.10(14) 5_656 . ? O3W Gd1 O4 84.90(15) . . ? O2W Gd1 O4 70.27(15) . . ? O1W Gd1 N1 90.79(17) . 2_756 ? O1W Gd1 N1 85.97(17) 5_656 2_756 ? O3W Gd1 N1 156.23(17) . 2_756 ? O2W Gd1 N1 77.1(2) . 2_756 ? O4 Gd1 N1 93.78(17) . 2_756 ? O1W Gd1 N3 78.01(15) . 2_756 ? O1W Gd1 N3 133.56(15) 5_656 2_756 ? O3W Gd1 N3 76.70(16) . 2_756 ? O2W Gd1 N3 138.57(15) . 2_756 ? O4 Gd1 N3 73.86(15) . 2_756 ? N1 Gd1 N3 125.76(16) 2_756 2_756 ? O1W Gd1 N2 84.56(15) . 2_756 ? O1W Gd1 N2 138.51(14) 5_656 2_756 ? O3W Gd1 N2 136.35(16) . 2_756 ? O2W Gd1 N2 120.3(2) . 2_756 ? O4 Gd1 N2 69.66(14) . 2_756 ? N1 Gd1 N2 63.51(16) 2_756 2_756 ? N3 Gd1 N2 62.68(15) 2_756 2_756 ? O1W Gd1 Gd1 33.94(10) . 5_656 ? O1W Gd1 Gd1 33.60(10) 5_656 5_656 ? O3W Gd1 Gd1 92.47(11) . 5_656 ? O2W Gd1 Gd1 107.88(12) . 5_656 ? O4 Gd1 Gd1 176.99(10) . 5_656 ? N1 Gd1 Gd1 88.04(13) 2_756 5_656 ? N3 Gd1 Gd1 106.98(10) 2_756 5_656 ? N2 Gd1 Gd1 113.32(10) 2_756 5_656 ? O6 S2 O4 111.7(3) . . ? O6 S2 O5 114.5(3) . . ? O4 S2 O5 112.1(3) . . ? O6 S2 C19 106.0(3) . . ? O4 S2 C19 105.9(3) . . ? O5 S2 C19 105.8(3) . . ? O1 S1 O2 112.2(5) . . ? O1 S1 O3 112.1(5) . . ? O2 S1 O3 113.4(5) . . ? O1 S1 C17 108.0(3) . . ? O2 S1 C17 104.5(4) . . ? O3 S1 C17 106.0(4) . . ? C10 N2 C6 117.9(5) . . ? C10 N2 Gd1 119.7(4) . 2_756 ? C6 N2 Gd1 119.3(4) . 2_756 ? N3 C15 C14 123.5(6) . . ? S2 O4 Gd1 151.3(3) . . ? C3 C2 C1 119.4(8) . . ? C15 N3 C11 117.5(5) . . ? C15 N3 Gd1 121.3(4) . 2_756 ? C11 N3 Gd1 121.3(4) . 2_756 ? C5 N1 C1 117.9(6) . . ? C5 N1 Gd1 122.0(4) . 2_756 ? C1 N1 Gd1 119.4(5) . 2_756 ? Gd1 O1W Gd1 112.46(16) . 5_656 ? C18 C19 C20 119.9(6) . . ? C18 C19 S2 119.4(5) . . ? C20 C19 S2 120.7(5) . . ? C17 C16 C21 117.5(6) . . ? C17 C16 C8 125.8(6) . . ? C21 C16 C8 116.6(5) . . ? N3 C11 C12 122.2(6) . . ? N3 C11 C10 115.9(5) . . ? C12 C11 C10 121.9(5) . . ? C21 C20 C19 120.2(6) . . ? C3 C4 C5 119.8(9) . . ? C8 C9 C10 120.0(6) . . ? C11 C12 C13 119.7(6) . . ? C19 C18 C17 120.9(6) . . ? N2 C10 C9 121.8(6) . . ? N2 C10 C11 116.1(5) . . ? C9 C10 C11 122.1(5) . . ? C18 C17 C16 120.4(6) . . ? C18 C17 S1 117.5(5) . . ? C16 C17 S1 122.0(5) . . ? N2 C6 C7 123.1(6) . . ? N2 C6 C5 116.0(5) . . ? C7 C6 C5 120.7(6) . . ? C13 C14 C15 118.0(7) . . ? C8 C7 C6 119.2(6) . . ? C20 C21 C16 120.7(6) . . ? C14 C13 C12 119.0(7) . . ? N1 C5 C4 122.1(6) . . ? N1 C5 C6 116.2(6) . . ? C4 C5 C6 121.7(6) . . ? N1 C1 C2 121.6(8) . . ? C4 C3 C2 119.0(8) . . ? C9 C8 C7 117.9(6) . . ? C9 C8 C16 121.3(6) . . ? C7 C8 C16 120.4(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.863 _refine_diff_density_min -0.998 _refine_diff_density_rms 0.160 _database_code_depnum_ccdc_archive 'CCDC 946680' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 N3 Nd O9 S2' _chemical_formula_weight 673.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.199(4) _cell_length_b 18.625(3) _cell_length_c 13.918(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.069(2) _cell_angle_gamma 90.00 _cell_volume 4662.4(15) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 787 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 18.00 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.920 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2656 _exptl_absorpt_coefficient_mu 2.467 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6129 _exptl_absorpt_correction_T_max 0.6515 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11776 _diffrn_reflns_av_R_equivalents 0.1121 _diffrn_reflns_av_sigmaI/netI 0.1775 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4092 _reflns_number_gt 1983 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0072P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4092 _refine_ls_number_parameters 334 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1163 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Nd1 Nd 0.14786(4) 0.18108(4) 0.27429(5) 0.0346(2) Uani 1 1 d . . . S2 S 0.04837(19) 0.12177(19) -0.6002(2) 0.0381(9) Uani 1 1 d . . . S1 S 0.1930(2) 0.2677(2) -0.2218(3) 0.0499(11) Uani 1 1 d . . . O4 O -0.0317(4) 0.1123(4) -0.6545(6) 0.042(2) Uani 1 1 d . . . O7 O 0.1812(5) 0.2909(5) 0.3822(7) 0.049(3) Uani 1 1 d . . . N2 N 0.1293(5) 0.1682(5) 0.0778(7) 0.031(3) Uani 1 1 d . . . C19 C 0.0725(6) 0.1312(6) -0.4608(9) 0.030(3) Uani 1 1 d . . . C6 C 0.0942(7) 0.2183(6) 0.0017(10) 0.035(3) Uani 1 1 d . . . C16 C 0.1064(6) 0.1467(6) -0.2434(9) 0.031(3) Uani 1 1 d . . . N3 N 0.2035(5) 0.0693(5) 0.2352(8) 0.037(3) Uani 1 1 d . . . N1 N 0.0809(5) 0.2824(5) 0.1438(8) 0.037(3) Uani 1 1 d . . . O5 O 0.0690(5) 0.1909(5) -0.6318(6) 0.067(3) Uani 1 1 d . . . C17 C 0.1334(6) 0.1965(6) -0.2923(9) 0.033(3) Uani 1 1 d . . . C20 C 0.0514(6) 0.0802(6) -0.4098(9) 0.039(3) Uani 1 1 d . . . H20A H 0.0259 0.0398 -0.4478 0.047 Uiso 1 1 calc R . . C21 C 0.0676(7) 0.0879(6) -0.3004(9) 0.041(3) Uani 1 1 d . . . H21A H 0.0520 0.0531 -0.2672 0.049 Uiso 1 1 calc R . . C10 C 0.1556(6) 0.1094(7) 0.0497(9) 0.032(3) Uani 1 1 d . . . O3 O 0.2366(5) 0.2779(5) -0.2804(6) 0.060(3) Uani 1 1 d . . . O8 O 0.2586(5) 0.3414(4) 0.5402(7) 0.050(3) Uani 1 1 d . . . C22 C 0.2308(9) 0.2878(8) 0.4759(15) 0.066(5) Uani 1 1 d . . . C9 C 0.1485(6) 0.1021(6) -0.0560(9) 0.034(3) Uani 1 1 d . . . H9A H 0.1655 0.0608 -0.0752 0.040 Uiso 1 1 calc R . . O2 O 0.2376(5) 0.2417(6) -0.1150(7) 0.088(4) Uani 1 1 d . . . C18 C 0.1151(6) 0.1880(6) -0.4012(9) 0.033(3) Uani 1 1 d . . . H18A H 0.1321 0.2214 -0.4344 0.040 Uiso 1 1 calc R . . C7 C 0.0876(6) 0.2141(6) -0.1021(9) 0.035(3) Uani 1 1 d . . . H7A H 0.0639 0.2504 -0.1519 0.043 Uiso 1 1 calc R . . C5 C 0.0641(7) 0.2784(7) 0.0375(10) 0.040(3) Uani 1 1 d . . . C15 C 0.2397(8) 0.0235(7) 0.3142(11) 0.052(4) Uani 1 1 d . . . H15A H 0.2430 0.0325 0.3820 0.062 Uiso 1 1 calc R . . O6 O 0.0891(5) 0.0639(5) -0.6117(7) 0.082(4) Uani 1 1 d . . . C11 C 0.1953(7) 0.0533(7) 0.1343(10) 0.039(3) Uani 1 1 d . . . C8 C 0.1163(6) 0.1563(6) -0.1299(9) 0.027(3) Uani 1 1 d . . . O1 O 0.1449(6) 0.3282(5) -0.2335(9) 0.084(3) Uani 1 1 d . . . C12 C 0.2261(7) -0.0082(7) 0.1145(11) 0.048(4) Uani 1 1 d . . . H12A H 0.2201 -0.0179 0.0454 0.058 Uiso 1 1 calc R . . C4 C 0.0162(8) 0.3275(7) -0.0363(12) 0.063(4) Uani 1 1 d . . . H4A H 0.0042 0.3226 -0.1089 0.076 Uiso 1 1 calc R . . C13 C 0.2650(7) -0.0541(8) 0.1969(11) 0.060(4) Uani 1 1 d . . . H13A H 0.2858 -0.0956 0.1847 0.072 Uiso 1 1 calc R . . C14 C 0.2735(8) -0.0385(7) 0.2991(11) 0.060(4) Uani 1 1 d . . . H14A H 0.3012 -0.0686 0.3569 0.072 Uiso 1 1 calc R . . C1 C 0.0550(8) 0.3363(7) 0.1789(12) 0.058(4) Uani 1 1 d . . . H1A H 0.0691 0.3404 0.2523 0.070 Uiso 1 1 calc R . . C2 C 0.0075(9) 0.3865(9) 0.1085(13) 0.084(6) Uani 1 1 d . . . H2A H -0.0107 0.4231 0.1352 0.100 Uiso 1 1 calc R . . C3 C -0.0143(9) 0.3836(8) -0.0040(14) 0.088(6) Uani 1 1 d . . . H3A H -0.0467 0.4169 -0.0524 0.105 Uiso 1 1 calc R . . O1W O 0.3268(8) -0.1172(8) 0.5294(12) 0.181(6) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd1 0.0418(4) 0.0444(4) 0.0213(4) -0.0063(4) 0.0174(3) -0.0103(5) S2 0.036(2) 0.062(2) 0.0172(18) -0.0089(18) 0.0128(17) -0.001(2) S1 0.054(3) 0.071(3) 0.032(2) -0.018(2) 0.025(2) -0.031(2) O4 0.033(5) 0.075(6) 0.019(5) -0.002(5) 0.014(4) 0.001(5) O7 0.062(7) 0.051(6) 0.015(5) -0.004(5) 0.001(5) -0.015(5) N2 0.031(6) 0.046(7) 0.022(6) -0.008(5) 0.019(5) -0.012(6) C19 0.035(8) 0.044(8) 0.016(7) -0.005(6) 0.015(6) -0.002(7) C6 0.035(8) 0.042(8) 0.030(8) 0.005(7) 0.017(7) 0.002(7) C16 0.024(7) 0.045(8) 0.020(7) -0.001(6) 0.007(6) -0.007(6) N3 0.047(7) 0.040(7) 0.020(6) 0.004(5) 0.013(6) -0.004(6) N1 0.038(7) 0.046(7) 0.032(7) -0.012(6) 0.019(6) -0.007(6) O5 0.080(7) 0.111(8) 0.026(5) -0.013(6) 0.037(5) -0.041(7) C17 0.034(8) 0.044(9) 0.017(7) 0.000(6) 0.009(6) -0.004(7) C20 0.053(9) 0.037(8) 0.025(8) -0.018(7) 0.015(7) -0.019(7) C21 0.052(9) 0.043(8) 0.030(8) 0.000(7) 0.021(7) -0.013(8) C10 0.023(7) 0.047(9) 0.026(8) -0.006(7) 0.013(6) -0.012(7) O3 0.065(7) 0.094(7) 0.032(6) -0.025(5) 0.031(5) -0.049(6) O8 0.068(7) 0.046(6) 0.036(6) -0.009(5) 0.023(5) -0.004(5) C22 0.074(14) 0.055(11) 0.102(16) 0.012(12) 0.070(13) 0.001(11) C9 0.038(8) 0.043(8) 0.030(8) -0.016(7) 0.025(7) -0.016(7) O2 0.088(8) 0.147(10) 0.021(6) -0.010(7) 0.019(6) -0.071(8) C18 0.036(8) 0.044(8) 0.030(8) 0.001(7) 0.024(7) -0.005(7) C7 0.042(9) 0.039(8) 0.028(8) 0.000(7) 0.019(7) -0.004(7) C5 0.049(10) 0.038(8) 0.034(9) 0.005(7) 0.021(8) -0.002(8) C15 0.080(12) 0.045(9) 0.038(9) 0.010(8) 0.034(9) -0.005(9) O6 0.076(8) 0.116(9) 0.028(6) -0.021(6) 0.001(5) 0.062(7) C11 0.036(9) 0.053(9) 0.024(8) 0.000(7) 0.009(7) -0.017(7) C8 0.027(7) 0.039(8) 0.015(7) 0.004(6) 0.009(6) -0.007(6) O1 0.089(8) 0.061(7) 0.119(9) -0.043(7) 0.062(7) -0.025(7) C12 0.055(10) 0.058(10) 0.036(9) -0.005(8) 0.025(8) 0.013(8) C4 0.093(13) 0.055(10) 0.057(11) 0.006(9) 0.046(10) 0.025(10) C13 0.057(11) 0.066(11) 0.044(10) -0.005(9) 0.011(9) 0.019(9) C14 0.071(12) 0.054(10) 0.040(10) 0.016(8) 0.012(9) 0.012(9) C1 0.075(12) 0.063(11) 0.049(10) 0.012(9) 0.038(9) 0.032(9) C2 0.116(16) 0.091(14) 0.062(13) -0.016(11) 0.056(12) 0.019(12) C3 0.118(16) 0.066(12) 0.073(14) 0.011(10) 0.038(12) 0.046(11) O1W 0.185(10) 0.223(10) 0.173(10) 0.051(8) 0.114(8) 0.025(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Nd1 O3 2.421(7) 7 ? Nd1 O8 2.443(9) 7_556 ? Nd1 O7 2.444(8) . ? Nd1 O5 2.485(7) 1_556 ? Nd1 O4 2.523(8) 2_554 ? Nd1 N3 2.539(9) . ? Nd1 N1 2.540(10) . ? Nd1 N2 2.597(8) . ? S2 O6 1.409(8) . ? S2 O4 1.451(8) . ? S2 O5 1.481(9) . ? S2 C19 1.780(11) . ? S1 O2 1.427(9) . ? S1 O1 1.448(9) . ? S1 O3 1.458(7) . ? S1 C17 1.759(11) . ? O4 Nd1 2.523(8) 2_554 ? O7 C22 1.233(18) . ? N2 C6 1.347(13) . ? N2 C10 1.349(13) . ? C19 C20 1.365(13) . ? C19 C18 1.376(14) . ? C6 C7 1.392(14) . ? C6 C5 1.465(15) . ? C16 C21 1.370(14) . ? C16 C17 1.402(13) . ? C16 C8 1.509(13) . ? N3 C15 1.320(13) . ? N3 C11 1.371(13) . ? N1 C1 1.325(13) . ? N1 C5 1.360(13) . ? O5 Nd1 2.485(7) 1_554 ? C17 C18 1.396(13) . ? C20 C21 1.411(14) . ? C10 C9 1.418(14) . ? C10 C11 1.504(15) . ? O3 Nd1 2.421(7) 7 ? O8 C22 1.286(17) . ? O8 Nd1 2.443(9) 7_556 ? C22 C22 1.60(3) 7_556 ? C9 C8 1.375(14) . ? C7 C8 1.359(13) . ? C5 C4 1.387(16) . ? C15 C14 1.405(15) . ? C11 C12 1.389(15) . ? C12 C13 1.357(15) . ? C4 C3 1.389(16) . ? C13 C14 1.384(16) . ? C1 C2 1.378(17) . ? C2 C3 1.422(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Nd1 O8 75.4(3) 7 7_556 ? O3 Nd1 O7 73.9(3) 7 . ? O8 Nd1 O7 68.3(3) 7_556 . ? O3 Nd1 O5 142.9(3) 7 1_556 ? O8 Nd1 O5 80.2(3) 7_556 1_556 ? O7 Nd1 O5 71.2(3) . 1_556 ? O3 Nd1 O4 140.8(2) 7 2_554 ? O8 Nd1 O4 130.6(3) 7_556 2_554 ? O7 Nd1 O4 138.1(3) . 2_554 ? O5 Nd1 O4 76.1(2) 1_556 2_554 ? O3 Nd1 N3 75.7(3) 7 . ? O8 Nd1 N3 83.2(3) 7_556 . ? O7 Nd1 N3 142.5(3) . . ? O5 Nd1 N3 128.7(3) 1_556 . ? O4 Nd1 N3 79.1(3) 2_554 . ? O3 Nd1 N1 89.0(3) 7 . ? O8 Nd1 N1 141.9(3) 7_556 . ? O7 Nd1 N1 74.1(3) . . ? O5 Nd1 N1 93.5(3) 1_556 . ? O4 Nd1 N1 82.7(3) 2_554 . ? N3 Nd1 N1 126.8(3) . . ? O3 Nd1 N2 75.0(3) 7 . ? O8 Nd1 N2 140.2(3) 7_556 . ? O7 Nd1 N2 126.3(3) . . ? O5 Nd1 N2 137.8(3) 1_556 . ? O4 Nd1 N2 67.2(2) 2_554 . ? N3 Nd1 N2 64.2(3) . . ? N1 Nd1 N2 62.7(3) . . ? O6 S2 O4 114.6(6) . . ? O6 S2 O5 112.0(6) . . ? O4 S2 O5 110.4(5) . . ? O6 S2 C19 108.4(5) . . ? O4 S2 C19 105.6(5) . . ? O5 S2 C19 105.2(5) . . ? O2 S1 O1 116.9(7) . . ? O2 S1 O3 111.8(6) . . ? O1 S1 O3 112.4(6) . . ? O2 S1 C17 105.8(6) . . ? O1 S1 C17 105.6(5) . . ? O3 S1 C17 102.7(5) . . ? S2 O4 Nd1 139.7(5) . 2_554 ? C22 O7 Nd1 118.3(10) . . ? C6 N2 C10 118.0(10) . . ? C6 N2 Nd1 122.4(7) . . ? C10 N2 Nd1 119.6(8) . . ? C20 C19 C18 118.6(10) . . ? C20 C19 S2 120.2(9) . . ? C18 C19 S2 121.2(9) . . ? N2 C6 C7 123.0(11) . . ? N2 C6 C5 114.4(11) . . ? C7 C6 C5 122.6(12) . . ? C21 C16 C17 119.7(10) . . ? C21 C16 C8 118.1(10) . . ? C17 C16 C8 122.3(10) . . ? C15 N3 C11 118.4(11) . . ? C15 N3 Nd1 118.9(8) . . ? C11 N3 Nd1 122.7(8) . . ? C1 N1 C5 119.8(12) . . ? C1 N1 Nd1 118.1(9) . . ? C5 N1 Nd1 121.7(8) . . ? S2 O5 Nd1 115.2(5) . 1_554 ? C18 C17 C16 118.8(11) . . ? C18 C17 S1 117.9(9) . . ? C16 C17 S1 123.2(9) . . ? C19 C20 C21 121.2(11) . . ? C16 C21 C20 119.7(11) . . ? N2 C10 C9 120.7(11) . . ? N2 C10 C11 118.5(11) . . ? C9 C10 C11 120.7(11) . . ? S1 O3 Nd1 147.0(5) . 7 ? C22 O8 Nd1 119.1(9) . 7_556 ? O7 C22 O8 126.0(14) . . ? O7 C22 C22 119(2) . 7_556 ? O8 C22 C22 115(2) . 7_556 ? C8 C9 C10 119.8(11) . . ? C19 C18 C17 121.7(10) . . ? C8 C7 C6 119.3(11) . . ? N1 C5 C4 121.0(12) . . ? N1 C5 C6 118.4(12) . . ? C4 C5 C6 120.6(12) . . ? N3 C15 C14 122.0(12) . . ? N3 C11 C12 121.8(12) . . ? N3 C11 C10 115.0(11) . . ? C12 C11 C10 123.1(12) . . ? C7 C8 C9 119.0(10) . . ? C7 C8 C16 121.4(11) . . ? C9 C8 C16 119.2(11) . . ? C13 C12 C11 119.4(13) . . ? C5 C4 C3 121.3(14) . . ? C12 C13 C14 119.3(13) . . ? C13 C14 C15 119.0(13) . . ? N1 C1 C2 121.1(13) . . ? C1 C2 C3 121.6(14) . . ? C4 C3 C2 115.1(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.545 _refine_diff_density_min -0.655 _refine_diff_density_rms 0.164 _database_code_depnum_ccdc_archive 'CCDC 946683' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 Eu N3 O9 S2' _chemical_formula_weight 681.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.1864(16) _cell_length_b 18.5532(15) _cell_length_c 13.8708(11) _cell_angle_alpha 90.00 _cell_angle_beta 117.3370(10) _cell_angle_gamma 90.00 _cell_volume 4614.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.962 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2680 _exptl_absorpt_coefficient_mu 2.961 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.4416 _exptl_absorpt_correction_T_max 0.6330 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13490 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 26.99 _reflns_number_total 5043 _reflns_number_gt 4061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+16.9874P] 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 5043 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 Eu1 Eu 0.148429(13) 0.183483(14) 0.272681(17) 0.02774(10) Uani 1 1 d . . . S2 S 0.04725(7) 0.12052(7) -0.60086(9) 0.0306(3) Uani 1 1 d . . . S1 S 0.19352(9) 0.26853(9) -0.22231(11) 0.0474(4) Uani 1 1 d . . . O4 O -0.03381(18) 0.1173(2) -0.6580(3) 0.0338(8) Uani 1 1 d . . . O7 O 0.1825(2) 0.2909(2) 0.3832(3) 0.0404(9) Uani 1 1 d . . . N2 N 0.1295(2) 0.1684(2) 0.0788(3) 0.0275(9) Uani 1 1 d . . . C19 C 0.0713(3) 0.1317(3) -0.4612(4) 0.0281(10) Uani 1 1 d . . . C6 C 0.0949(3) 0.2200(3) 0.0039(4) 0.0293(10) Uani 1 1 d . . . C16 C 0.1061(3) 0.1476(3) -0.2436(4) 0.0293(10) Uani 1 1 d . . . N3 N 0.2011(2) 0.0705(2) 0.2366(3) 0.0322(9) Uani 1 1 d . . . N1 N 0.0808(3) 0.2846(3) 0.1438(4) 0.0388(10) Uani 1 1 d . . . O5 O 0.0732(3) 0.1856(3) -0.6322(3) 0.0549(13) Uani 1 1 d . . . C17 C 0.1316(3) 0.1974(3) -0.2946(4) 0.0311(11) Uani 1 1 d . . . C20 C 0.0490(3) 0.0801(3) -0.4096(4) 0.0392(13) Uani 1 1 d . . . H20A H 0.0216 0.0403 -0.4481 0.047 Uiso 1 1 calc R . . C21 C 0.0676(3) 0.0879(3) -0.3014(4) 0.0361(12) Uani 1 1 d . . . H21A H 0.0539 0.0523 -0.2668 0.043 Uiso 1 1 calc R . . C10 C 0.1555(3) 0.1105(3) 0.0507(4) 0.0280(10) Uani 1 1 d . . . O3 O 0.2391(2) 0.2764(3) -0.2781(3) 0.0542(12) Uani 1 1 d . . . O8 O 0.2602(2) 0.3403(2) 0.5434(3) 0.0412(9) Uani 1 1 d . . . C22 C 0.2338(3) 0.2882(3) 0.4792(4) 0.0342(11) Uani 1 1 d . . . C9 C 0.1488(3) 0.1022(3) -0.0540(4) 0.0316(11) Uani 1 1 d . . . H9A H 0.1663 0.0606 -0.0722 0.038 Uiso 1 1 calc R . . O2 O 0.2366(3) 0.2437(4) -0.1138(3) 0.090(2) Uani 1 1 d . . . C18 C 0.1135(3) 0.1892(3) -0.4038(4) 0.0319(11) Uani 1 1 d . . . H18A H 0.1300 0.2228 -0.4377 0.038 Uiso 1 1 calc R . . C7 C 0.0882(3) 0.2154(3) -0.0999(4) 0.0324(11) Uani 1 1 d . . . H7A H 0.0650 0.2522 -0.1497 0.039 Uiso 1 1 calc R . . C5 C 0.0630(3) 0.2817(3) 0.0384(4) 0.0347(11) Uani 1 1 d . . . C15 C 0.2397(4) 0.0247(3) 0.3179(5) 0.0501(15) Uani 1 1 d . . . H15A H 0.2457 0.0356 0.3869 0.060 Uiso 1 1 calc R . . O6 O 0.0822(3) 0.0564(3) -0.6105(3) 0.0719(16) Uani 1 1 d . . . C11 C 0.1951(3) 0.0558(3) 0.1364(4) 0.0304(10) Uani 1 1 d . . . C8 C 0.1162(3) 0.1557(3) -0.1292(4) 0.0306(11) Uani 1 1 d . . . O1 O 0.1483(3) 0.3304(3) -0.2340(6) 0.096(2) Uani 1 1 d . . . C12 C 0.2253(3) -0.0069(3) 0.1187(4) 0.0439(13) Uani 1 1 d . . . H12A H 0.2203 -0.0169 0.0500 0.053 Uiso 1 1 calc R . . C4 C 0.0162(5) 0.3310(4) -0.0347(6) 0.065(2) Uani 1 1 d . . . H4A H 0.0039 0.3269 -0.1078 0.078 Uiso 1 1 calc R . . C13 C 0.2626(4) -0.0541(4) 0.2023(5) 0.0571(17) Uani 1 1 d . . . H13A H 0.2819 -0.0967 0.1901 0.069 Uiso 1 1 calc R . . C14 C 0.2711(4) -0.0382(4) 0.3035(6) 0.0591(17) Uani 1 1 d . . . H14A H 0.2975 -0.0689 0.3616 0.071 Uiso 1 1 calc R . . C1 C 0.0537(4) 0.3398(4) 0.1761(5) 0.0542(16) Uani 1 1 d . . . H1A H 0.0676 0.3434 0.2498 0.065 Uiso 1 1 calc R . . C2 C 0.0074(5) 0.3910(4) 0.1099(6) 0.076(2) Uani 1 1 d . . . H2A H -0.0102 0.4279 0.1375 0.091 Uiso 1 1 calc R . . C3 C -0.0131(6) 0.3872(4) 0.0005(7) 0.086(3) Uani 1 1 d . . . H3A H -0.0453 0.4209 -0.0480 0.103 Uiso 1 1 calc R . . O1W O 0.3221(6) -0.1213(7) 0.5258(9) 0.194(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 Eu1 0.03307(15) 0.03485(16) 0.01698(14) -0.00607(9) 0.01295(11) -0.00861(10) S2 0.0279(6) 0.0487(8) 0.0158(5) -0.0073(5) 0.0106(4) 0.0001(5) S1 0.0526(8) 0.0648(10) 0.0341(7) -0.0239(7) 0.0277(7) -0.0338(8) O4 0.0307(17) 0.051(2) 0.0181(16) 0.0018(15) 0.0098(14) 0.0036(16) O7 0.051(2) 0.039(2) 0.0253(18) -0.0037(16) 0.0126(17) -0.0087(18) N2 0.030(2) 0.034(2) 0.0205(19) -0.0057(16) 0.0142(17) -0.0086(17) C19 0.029(2) 0.037(3) 0.018(2) -0.0059(19) 0.0103(19) -0.002(2) C6 0.033(2) 0.037(3) 0.020(2) -0.004(2) 0.014(2) -0.011(2) C16 0.031(2) 0.041(3) 0.018(2) -0.002(2) 0.0132(19) -0.004(2) N3 0.038(2) 0.039(2) 0.0190(19) 0.0017(17) 0.0134(17) -0.0025(19) N1 0.050(3) 0.041(3) 0.030(2) -0.004(2) 0.022(2) 0.001(2) O5 0.057(3) 0.089(4) 0.027(2) -0.015(2) 0.027(2) -0.033(2) C17 0.033(2) 0.042(3) 0.020(2) -0.009(2) 0.013(2) -0.011(2) C20 0.054(3) 0.040(3) 0.027(3) -0.012(2) 0.022(2) -0.017(3) C21 0.048(3) 0.039(3) 0.024(2) -0.005(2) 0.019(2) -0.012(2) C10 0.031(2) 0.033(3) 0.020(2) -0.0054(19) 0.0127(19) -0.010(2) O3 0.048(2) 0.088(3) 0.036(2) -0.022(2) 0.0274(19) -0.039(2) O8 0.048(2) 0.044(2) 0.0247(19) -0.0065(17) 0.0111(17) -0.0100(18) C22 0.038(3) 0.042(3) 0.027(3) -0.002(2) 0.019(2) -0.007(2) C9 0.037(3) 0.038(3) 0.024(2) -0.008(2) 0.018(2) -0.006(2) O2 0.081(3) 0.153(6) 0.025(2) -0.014(3) 0.014(2) -0.079(4) C18 0.034(3) 0.043(3) 0.021(2) -0.003(2) 0.015(2) -0.012(2) C7 0.037(3) 0.039(3) 0.023(2) -0.002(2) 0.015(2) -0.003(2) C5 0.047(3) 0.035(3) 0.027(3) -0.002(2) 0.022(2) -0.005(2) C15 0.072(4) 0.051(4) 0.033(3) 0.008(3) 0.029(3) 0.005(3) O6 0.069(3) 0.099(4) 0.028(2) -0.016(2) 0.005(2) 0.049(3) C11 0.036(2) 0.037(3) 0.019(2) -0.007(2) 0.013(2) -0.010(2) C8 0.035(3) 0.042(3) 0.017(2) -0.003(2) 0.014(2) -0.012(2) O1 0.100(5) 0.066(4) 0.137(7) -0.056(4) 0.065(5) -0.035(3) C12 0.055(3) 0.046(3) 0.031(3) -0.005(2) 0.020(3) 0.005(3) C4 0.112(6) 0.054(4) 0.038(4) 0.007(3) 0.042(4) 0.025(4) C13 0.067(4) 0.052(4) 0.050(4) 0.000(3) 0.026(3) 0.014(3) C14 0.074(4) 0.050(4) 0.050(4) 0.014(3) 0.025(3) 0.015(3) C1 0.072(4) 0.060(4) 0.039(3) -0.003(3) 0.033(3) 0.011(4) C2 0.120(7) 0.059(5) 0.065(5) 0.004(4) 0.057(5) 0.035(5) C3 0.138(8) 0.069(5) 0.062(5) 0.020(4) 0.056(5) 0.046(5) O1W 0.163(9) 0.254(13) 0.197(10) 0.129(10) 0.109(8) 0.064(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 Eu1 O3 2.357(4) 7 ? Eu1 O8 2.405(4) 7_556 ? Eu1 O7 2.414(4) . ? Eu1 O5 2.427(4) 1_556 ? Eu1 O4 2.452(3) 2_554 ? Eu1 N3 2.502(4) . ? Eu1 N1 2.518(5) . ? Eu1 N2 2.551(4) . ? Eu1 C22 3.202(5) 7_556 ? Eu1 C22 3.228(5) . ? Eu1 S2 3.4502(12) 1_556 ? S2 O6 1.420(4) . ? S2 O4 1.455(3) . ? S2 O5 1.459(4) . ? S2 C19 1.779(5) . ? S2 Eu1 3.4502(12) 1_554 ? S1 O2 1.425(5) . ? S1 O1 1.429(7) . ? S1 O3 1.456(4) . ? S1 C17 1.778(5) . ? O4 Eu1 2.452(3) 2_554 ? O7 C22 1.258(6) . ? N2 C10 1.332(6) . ? N2 C6 1.347(6) . ? C19 C18 1.369(7) . ? C19 C20 1.388(7) . ? C6 C7 1.386(6) . ? C6 C5 1.496(7) . ? C16 C21 1.377(7) . ? C16 C17 1.398(7) . ? C16 C8 1.511(6) . ? N3 C15 1.339(7) . ? N3 C11 1.367(6) . ? N1 C5 1.336(6) . ? N1 C1 1.332(8) . ? O5 Eu1 2.427(4) 1_554 ? C17 C18 1.394(7) . ? C20 C21 1.378(7) . ? C10 C9 1.403(6) . ? C10 C11 1.486(7) . ? O3 Eu1 2.357(4) 7 ? O8 C22 1.255(6) . ? O8 Eu1 2.405(4) 7_556 ? C22 C22 1.558(11) 7_556 ? C22 Eu1 3.202(5) 7_556 ? C9 C8 1.371(7) . ? C7 C8 1.387(7) . ? C5 C4 1.370(9) . ? C15 C14 1.386(9) . ? C11 C12 1.385(8) . ? C12 C13 1.370(9) . ? C4 C3 1.394(10) . ? C13 C14 1.366(9) . ? C1 C2 1.354(10) . ? C2 C3 1.379(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Eu1 O8 76.49(14) 7 7_556 ? O3 Eu1 O7 74.29(14) 7 . ? O8 Eu1 O7 67.78(13) 7_556 . ? O3 Eu1 O5 144.25(13) 7 1_556 ? O8 Eu1 O5 78.00(14) 7_556 1_556 ? O7 Eu1 O5 73.08(14) . 1_556 ? O3 Eu1 O4 141.88(12) 7 2_554 ? O8 Eu1 O4 129.18(12) 7_556 2_554 ? O7 Eu1 O4 137.28(13) . 2_554 ? O5 Eu1 O4 73.82(12) 1_556 2_554 ? O3 Eu1 N3 77.25(16) 7 . ? O8 Eu1 N3 82.48(13) 7_556 . ? O7 Eu1 N3 142.64(13) . . ? O5 Eu1 N3 123.47(15) 1_556 . ? O4 Eu1 N3 79.16(13) 2_554 . ? O3 Eu1 N1 89.26(17) 7 . ? O8 Eu1 N1 142.34(14) 7_556 . ? O7 Eu1 N1 74.87(14) . . ? O5 Eu1 N1 95.97(16) 1_556 . ? O4 Eu1 N1 82.55(14) 2_554 . ? N3 Eu1 N1 128.59(13) . . ? O3 Eu1 N2 75.18(12) 7 . ? O8 Eu1 N2 140.26(14) 7_556 . ? O7 Eu1 N2 128.35(13) . . ? O5 Eu1 N2 138.28(13) 1_556 . ? O4 Eu1 N2 67.73(11) 2_554 . ? N3 Eu1 N2 64.51(13) . . ? N1 Eu1 N2 64.09(13) . . ? O3 Eu1 C22 71.66(13) 7 7_556 ? O8 Eu1 C22 20.10(14) 7_556 7_556 ? O7 Eu1 C22 47.77(13) . 7_556 ? O5 Eu1 C22 75.76(13) 1_556 7_556 ? O4 Eu1 C22 142.47(12) 2_554 7_556 ? N3 Eu1 C22 100.25(13) . 7_556 ? N1 Eu1 C22 122.26(14) . 7_556 ? N2 Eu1 C22 145.95(12) . 7_556 ? O3 Eu1 C22 70.60(13) 7 . ? O8 Eu1 C22 48.10(14) 7_556 . ? O7 Eu1 C22 19.78(14) . . ? O5 Eu1 C22 73.75(13) 1_556 . ? O4 Eu1 C22 146.89(12) 2_554 . ? N3 Eu1 C22 125.37(13) . . ? N1 Eu1 C22 94.35(14) . . ? N2 Eu1 C22 139.62(12) . . ? C22 Eu1 C22 28.03(19) 7_556 . ? O3 Eu1 S2 151.29(10) 7 1_556 ? O8 Eu1 S2 75.10(10) 7_556 1_556 ? O7 Eu1 S2 91.13(9) . 1_556 ? O5 Eu1 S2 20.70(11) 1_556 1_556 ? O4 Eu1 S2 63.76(8) 2_554 1_556 ? N3 Eu1 S2 102.90(9) . 1_556 ? N1 Eu1 S2 111.04(11) . 1_556 ? N2 Eu1 S2 131.41(9) . 1_556 ? C22 Eu1 S2 80.20(9) 7_556 1_556 ? C22 Eu1 S2 87.25(9) . 1_556 ? O6 S2 O4 113.4(3) . . ? O6 S2 O5 113.8(3) . . ? O4 S2 O5 109.9(2) . . ? O6 S2 C19 107.5(2) . . ? O4 S2 C19 105.9(2) . . ? O5 S2 C19 105.8(2) . . ? O6 S2 Eu1 78.5(3) . 1_554 ? O4 S2 Eu1 121.16(14) . 1_554 ? O5 S2 Eu1 36.02(18) . 1_554 ? C19 S2 Eu1 125.76(16) . 1_554 ? O2 S1 O1 115.3(4) . . ? O2 S1 O3 111.4(3) . . ? O1 S1 O3 112.7(4) . . ? O2 S1 C17 106.6(3) . . ? O1 S1 C17 106.6(3) . . ? O3 S1 C17 103.1(2) . . ? S2 O4 Eu1 145.3(2) . 2_554 ? C22 O7 Eu1 119.7(4) . . ? C10 N2 C6 118.8(4) . . ? C10 N2 Eu1 120.6(3) . . ? C6 N2 Eu1 120.6(3) . . ? C18 C19 C20 120.0(4) . . ? C18 C19 S2 120.7(4) . . ? C20 C19 S2 119.3(4) . . ? N2 C6 C7 121.8(5) . . ? N2 C6 C5 116.3(4) . . ? C7 C6 C5 121.9(5) . . ? C21 C16 C17 118.4(4) . . ? C21 C16 C8 117.4(4) . . ? C17 C16 C8 124.1(4) . . ? C15 N3 C11 118.4(5) . . ? C15 N3 Eu1 120.0(4) . . ? C11 N3 Eu1 121.6(3) . . ? C5 N1 C1 117.0(5) . . ? C5 N1 Eu1 122.2(4) . . ? C1 N1 Eu1 120.4(4) . . ? S2 O5 Eu1 123.3(3) . 1_554 ? C18 C17 C16 120.3(4) . . ? C18 C17 S1 117.3(4) . . ? C16 C17 S1 122.2(4) . . ? C21 C20 C19 119.9(5) . . ? C20 C21 C16 121.2(5) . . ? N2 C10 C9 121.9(5) . . ? N2 C10 C11 117.2(4) . . ? C9 C10 C11 120.9(5) . . ? S1 O3 Eu1 148.1(2) . 7 ? C22 O8 Eu1 118.7(4) . 7_556 ? O7 C22 O8 126.6(5) . . ? O7 C22 C22 115.4(6) . 7_556 ? O8 C22 C22 118.0(6) . 7_556 ? O7 C22 Eu1 167.3(4) . 7_556 ? O8 C22 Eu1 41.2(3) . 7_556 ? C22 C22 Eu1 76.9(4) 7_556 7_556 ? O7 C22 Eu1 40.5(3) . . ? O8 C22 Eu1 166.7(4) . . ? C22 C22 Eu1 75.1(4) 7_556 . ? Eu1 C22 Eu1 151.97(19) 7_556 . ? C8 C9 C10 119.5(5) . . ? C19 C18 C17 120.0(5) . . ? C6 C7 C8 119.7(5) . . ? N1 C5 C4 122.0(5) . . ? N1 C5 C6 116.2(5) . . ? C4 C5 C6 121.8(5) . . ? N3 C15 C14 122.7(5) . . ? N3 C11 C12 120.5(5) . . ? N3 C11 C10 116.2(4) . . ? C12 C11 C10 123.4(4) . . ? C9 C8 C7 118.2(4) . . ? C9 C8 C16 120.9(5) . . ? C7 C8 C16 120.7(5) . . ? C13 C12 C11 120.2(5) . . ? C5 C4 C3 120.0(6) . . ? C12 C13 C14 119.4(6) . . ? C15 C14 C13 118.7(6) . . ? N1 C1 C2 125.0(6) . . ? C1 C2 C3 118.4(7) . . ? C2 C3 C4 117.5(7) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.601 _refine_diff_density_min -0.626 _refine_diff_density_rms 0.134 _database_code_depnum_ccdc_archive 'CCDC 946685' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 N3 O9 S2 Tb' _chemical_formula_weight 688.41 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' 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' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.084(4) _cell_length_b 18.534(4) _cell_length_c 13.831(4) _cell_angle_alpha 90.00 _cell_angle_beta 117.639(2) _cell_angle_gamma 90.00 _cell_volume 4560.9(19) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1102 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 18.74 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.005 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2696 _exptl_absorpt_coefficient_mu 3.346 _exptl_absorpt_correction_type multi-scna _exptl_absorpt_correction_T_min 0.4884 _exptl_absorpt_correction_T_max 0.6165 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13456 _diffrn_reflns_av_R_equivalents 0.0832 _diffrn_reflns_av_sigmaI/netI 0.1117 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4980 _reflns_number_gt 3023 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0634P)^2^+16.9874P] 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 4980 _refine_ls_number_parameters 334 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1069 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1529 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.270 _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 Tb1 Tb 0.14899(3) 0.18457(3) 0.27245(4) 0.0274(2) Uani 1 1 d . . . S2 S 0.04676(17) 0.11939(17) -0.6010(2) 0.0283(7) Uani 1 1 d . . . S1 S 0.1941(2) 0.2682(2) -0.2214(3) 0.0480(10) Uani 1 1 d . . . O4 O -0.0354(4) 0.1192(4) -0.6596(6) 0.032(2) Uani 1 1 d . . . O7 O 0.1827(5) 0.2907(5) 0.3829(7) 0.039(2) Uani 1 1 d . . . N2 N 0.1302(5) 0.1691(5) 0.0808(8) 0.026(2) Uani 1 1 d . . . C19 C 0.0706(6) 0.1307(6) -0.4618(9) 0.025(3) Uani 1 1 d . . . C6 C 0.0944(7) 0.2195(6) 0.0038(9) 0.028(3) Uani 1 1 d . . . C16 C 0.1067(7) 0.1473(7) -0.2421(9) 0.029(3) Uani 1 1 d . . . N3 N 0.2010(6) 0.0724(6) 0.2397(8) 0.031(2) Uani 1 1 d . . . N1 N 0.0800(6) 0.2845(6) 0.1445(8) 0.034(2) Uani 1 1 d . . . O5 O 0.0762(5) 0.1833(5) -0.6308(7) 0.051(3) Uani 1 1 d . . . C17 C 0.1313(7) 0.1981(6) -0.2942(9) 0.029(3) Uani 1 1 d . . . C20 C 0.0493(7) 0.0797(7) -0.4102(9) 0.034(3) Uani 1 1 d . . . H20A H 0.0229 0.0393 -0.4487 0.041 Uiso 1 1 calc R . . C21 C 0.0667(7) 0.0875(7) -0.3008(10) 0.034(3) Uani 1 1 d . . . H21A H 0.0514 0.0526 -0.2671 0.041 Uiso 1 1 calc R . . C10 C 0.1570(6) 0.1100(6) 0.0521(9) 0.024(2) Uani 1 1 d . . . O3 O 0.2395(5) 0.2760(5) -0.2781(7) 0.048(3) Uani 1 1 d . . . O8 O 0.2592(5) 0.3397(5) 0.5450(7) 0.041(2) Uani 1 1 d . . . C22 C 0.2336(8) 0.2880(7) 0.4790(11) 0.038(3) Uani 1 1 d . . . C9 C 0.1491(7) 0.1016(7) -0.0515(9) 0.031(3) Uani 1 1 d . . . H9A H 0.1659 0.0597 -0.0700 0.037 Uiso 1 1 calc R . . O2 O 0.2373(7) 0.2430(8) -0.1126(8) 0.097(5) Uani 1 1 d . . . C18 C 0.1131(6) 0.1878(7) -0.4030(9) 0.032(3) Uani 1 1 d . . . H18A H 0.1303 0.2209 -0.4370 0.038 Uiso 1 1 calc R . . C7 C 0.0887(7) 0.2157(7) -0.0983(9) 0.034(3) Uani 1 1 d . . . H7A H 0.0666 0.2533 -0.1474 0.041 Uiso 1 1 calc R . . C5 C 0.0638(8) 0.2813(7) 0.0395(11) 0.039(3) Uani 1 1 d . . . C15 C 0.2401(8) 0.0257(7) 0.3213(11) 0.044(4) Uani 1 1 d . . . H15A H 0.2461 0.0367 0.3904 0.053 Uiso 1 1 calc R . . O6 O 0.0790(5) 0.0533(5) -0.6094(7) 0.056(3) Uani 1 1 d . . . C11 C 0.1954(6) 0.0561(7) 0.1381(9) 0.030(3) Uani 1 1 d . . . C8 C 0.1157(7) 0.1560(7) -0.1292(10) 0.030(3) Uani 1 1 d . . . O1 O 0.1476(7) 0.3303(6) -0.2337(13) 0.096(5) Uani 1 1 d . . . C12 C 0.2255(8) -0.0073(7) 0.1221(12) 0.045(4) Uani 1 1 d . . . H12A H 0.2195 -0.0184 0.0529 0.054 Uiso 1 1 calc R . . C4 C 0.0170(10) 0.3320(8) -0.0335(14) 0.063(5) Uani 1 1 d . . . H4A H 0.0059 0.3287 -0.1066 0.076 Uiso 1 1 calc R . . C13 C 0.2639(8) -0.0536(8) 0.2067(12) 0.052(4) Uani 1 1 d . . . H13A H 0.2846 -0.0957 0.1958 0.063 Uiso 1 1 calc R . . C14 C 0.2716(9) -0.0371(8) 0.3090(12) 0.057(4) Uani 1 1 d . . . H14A H 0.2975 -0.0679 0.3679 0.068 Uiso 1 1 calc R . . C1 C 0.0530(8) 0.3398(7) 0.1779(12) 0.048(4) Uani 1 1 d . . . H1A H 0.0667 0.3436 0.2518 0.058 Uiso 1 1 calc R . . C2 C 0.0067(11) 0.3904(9) 0.1091(14) 0.070(5) Uani 1 1 d . . . H2A H -0.0114 0.4272 0.1361 0.084 Uiso 1 1 calc R . . C3 C -0.0138(12) 0.3877(10) -0.0001(15) 0.084(6) Uani 1 1 d . . . H3A H -0.0465 0.4213 -0.0491 0.101 Uiso 1 1 calc R . . O1W O 0.159(3) 0.392(3) -0.057(5) 0.69(2) Uani 1 1 d U . . H1WA H 0.1498 0.3825 -0.1212 1.034 Uiso 1 1 d R . . H1WB H 0.1814 0.3596 -0.0165 1.034 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Tb1 0.0337(3) 0.0341(3) 0.0171(3) -0.0056(3) 0.0139(2) -0.0080(3) S2 0.0287(16) 0.0444(19) 0.0139(14) -0.0052(13) 0.0117(12) -0.0007(14) S1 0.057(2) 0.063(3) 0.036(2) -0.0242(18) 0.0311(18) -0.034(2) O4 0.029(5) 0.048(5) 0.016(4) 0.007(4) 0.009(3) 0.006(4) O7 0.045(5) 0.037(5) 0.025(5) -0.008(4) 0.008(4) -0.008(4) N2 0.025(5) 0.038(6) 0.021(5) -0.005(4) 0.015(4) -0.007(4) C19 0.030(6) 0.029(6) 0.016(6) -0.004(5) 0.011(5) -0.002(5) C6 0.038(7) 0.026(6) 0.025(7) -0.004(5) 0.019(6) -0.008(5) C16 0.029(7) 0.043(8) 0.016(6) 0.001(5) 0.011(5) 0.000(6) N3 0.036(6) 0.045(6) 0.016(5) -0.004(5) 0.014(4) -0.008(5) N1 0.049(7) 0.038(6) 0.030(6) 0.000(5) 0.030(5) 0.003(5) O5 0.058(6) 0.083(7) 0.018(5) -0.018(5) 0.024(4) -0.028(6) C17 0.031(7) 0.041(8) 0.015(6) -0.003(5) 0.010(5) -0.002(5) C20 0.047(8) 0.036(7) 0.016(6) -0.009(5) 0.013(6) -0.019(6) C21 0.048(8) 0.035(7) 0.023(7) -0.007(5) 0.021(6) -0.008(6) C10 0.025(6) 0.022(6) 0.024(6) -0.003(5) 0.012(5) -0.005(5) O3 0.046(6) 0.073(7) 0.034(5) -0.020(5) 0.026(5) -0.037(5) O8 0.055(6) 0.039(5) 0.026(5) -0.009(4) 0.017(4) -0.006(4) C22 0.041(8) 0.041(8) 0.032(8) -0.004(6) 0.017(6) -0.006(6) C9 0.039(7) 0.033(7) 0.023(6) -0.004(5) 0.016(5) -0.006(6) O2 0.089(9) 0.169(13) 0.025(6) -0.025(7) 0.020(6) -0.098(9) C18 0.032(7) 0.042(7) 0.022(6) -0.003(6) 0.014(5) -0.005(6) C7 0.047(8) 0.039(7) 0.018(6) 0.000(5) 0.017(6) -0.005(6) C5 0.047(8) 0.031(7) 0.041(8) 0.007(6) 0.021(7) 0.001(6) C15 0.064(10) 0.042(8) 0.029(8) 0.006(6) 0.024(7) 0.000(7) O6 0.062(6) 0.065(7) 0.025(5) -0.008(5) 0.006(5) 0.038(5) C11 0.027(6) 0.041(7) 0.022(6) -0.012(5) 0.012(5) -0.011(6) C8 0.030(7) 0.044(7) 0.021(6) -0.002(5) 0.016(5) -0.009(6) O1 0.102(11) 0.060(8) 0.148(14) -0.061(8) 0.077(10) -0.040(7) C12 0.051(9) 0.049(9) 0.040(8) -0.013(7) 0.024(7) 0.009(7) C4 0.105(14) 0.057(11) 0.050(10) 0.009(8) 0.055(10) 0.018(9) C13 0.066(10) 0.042(9) 0.047(9) 0.008(7) 0.024(8) 0.029(8) C14 0.078(11) 0.050(10) 0.027(8) 0.011(7) 0.011(8) 0.014(8) C1 0.050(9) 0.048(9) 0.038(8) -0.005(7) 0.014(7) 0.014(7) C2 0.108(15) 0.057(11) 0.057(11) -0.004(9) 0.048(11) 0.035(10) C3 0.126(18) 0.076(13) 0.058(12) 0.017(10) 0.049(12) 0.041(12) O1W 0.69(2) 0.70(2) 0.69(2) -0.024(13) 0.326(15) -0.541 _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 Tb1 O3 2.322(8) 7 ? Tb1 O8 2.379(9) 7_556 ? Tb1 O7 2.388(8) . ? Tb1 O5 2.396(9) 1_556 ? Tb1 O4 2.409(8) 2_554 ? Tb1 N3 2.462(10) . ? Tb1 N1 2.491(10) . ? Tb1 N2 2.514(9) . ? S2 O6 1.416(9) . ? S2 O4 1.462(8) . ? S2 O5 1.466(10) . ? S2 C19 1.766(11) . ? S1 O2 1.423(12) . ? S1 O1 1.443(13) . ? S1 O3 1.460(9) . ? S1 C17 1.763(12) . ? O4 Tb1 2.409(8) 2_554 ? O7 C22 1.247(15) . ? N2 C10 1.358(14) . ? N2 C6 1.347(15) . ? C19 C18 1.366(15) . ? C19 C20 1.367(16) . ? C6 C7 1.366(16) . ? C6 C5 1.486(18) . ? C16 C21 1.388(16) . ? C16 C17 1.407(16) . ? C16 C8 1.495(16) . ? N3 C15 1.347(16) . ? N3 C11 1.390(14) . ? N1 C5 1.335(16) . ? N1 C1 1.338(16) . ? O5 Tb1 2.396(9) 1_554 ? C17 C18 1.387(15) . ? C20 C21 1.394(15) . ? C10 C9 1.375(16) . ? C10 C11 1.468(16) . ? O3 Tb1 2.322(8) 7 ? O8 C22 1.257(15) . ? O8 Tb1 2.379(9) 7_556 ? C22 C22 1.55(3) 7_556 ? C9 C8 1.397(17) . ? C7 C8 1.383(17) . ? C5 C4 1.38(2) . ? C15 C14 1.373(19) . ? C11 C12 1.385(17) . ? C12 C13 1.366(19) . ? C4 C3 1.39(2) . ? C13 C14 1.38(2) . ? C1 C2 1.35(2) . ? C2 C3 1.37(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Tb1 O8 76.3(3) 7 7_556 ? O3 Tb1 O7 74.7(3) 7 . ? O8 Tb1 O7 68.1(3) 7_556 . ? O3 Tb1 O5 144.4(3) 7 1_556 ? O8 Tb1 O5 77.2(3) 7_556 1_556 ? O7 Tb1 O5 73.5(3) . 1_556 ? O3 Tb1 O4 142.1(3) 7 2_554 ? O8 Tb1 O4 128.8(3) 7_556 2_554 ? O7 Tb1 O4 137.0(3) . 2_554 ? O5 Tb1 O4 73.5(3) 1_556 2_554 ? O3 Tb1 N3 77.7(3) 7 . ? O8 Tb1 N3 81.3(3) 7_556 . ? O7 Tb1 N3 142.6(3) . . ? O5 Tb1 N3 121.0(3) 1_556 . ? O4 Tb1 N3 79.1(3) 2_554 . ? O3 Tb1 N1 90.0(4) 7 . ? O8 Tb1 N1 142.8(3) 7_556 . ? O7 Tb1 N1 75.0(3) . . ? O5 Tb1 N1 97.0(3) 1_556 . ? O4 Tb1 N1 82.3(3) 2_554 . ? N3 Tb1 N1 129.9(3) . . ? O3 Tb1 N2 75.1(3) 7 . ? O8 Tb1 N2 139.5(3) 7_556 . ? O7 Tb1 N2 128.9(3) . . ? O5 Tb1 N2 139.0(3) 1_556 . ? O4 Tb1 N2 68.0(3) 2_554 . ? N3 Tb1 N2 65.1(3) . . ? N1 Tb1 N2 64.8(3) . . ? O6 S2 O4 113.2(6) . . ? O6 S2 O5 114.6(6) . . ? O4 S2 O5 110.1(5) . . ? O6 S2 C19 106.8(5) . . ? O4 S2 C19 105.7(5) . . ? O5 S2 C19 105.6(5) . . ? O2 S1 O1 115.5(9) . . ? O2 S1 O3 112.0(7) . . ? O1 S1 O3 112.9(8) . . ? O2 S1 C17 106.6(6) . . ? O1 S1 C17 105.5(6) . . ? O3 S1 C17 103.1(5) . . ? S2 O4 Tb1 147.6(5) . 2_554 ? C22 O7 Tb1 119.8(8) . . ? C10 N2 C6 117.9(10) . . ? C10 N2 Tb1 121.0(7) . . ? C6 N2 Tb1 121.2(7) . . ? C18 C19 C20 119.0(11) . . ? C18 C19 S2 121.4(9) . . ? C20 C19 S2 119.6(9) . . ? N2 C6 C7 122.6(11) . . ? N2 C6 C5 115.1(10) . . ? C7 C6 C5 122.3(12) . . ? C21 C16 C17 118.7(11) . . ? C21 C16 C8 117.0(11) . . ? C17 C16 C8 124.1(11) . . ? C15 N3 C11 116.7(11) . . ? C15 N3 Tb1 121.4(8) . . ? C11 N3 Tb1 121.8(8) . . ? C5 N1 C1 118.5(12) . . ? C5 N1 Tb1 120.9(8) . . ? C1 N1 Tb1 120.3(9) . . ? S2 O5 Tb1 126.5(6) . 1_554 ? C18 C17 C16 119.0(11) . . ? C18 C17 S1 118.6(9) . . ? C16 C17 S1 121.9(9) . . ? C21 C20 C19 120.9(11) . . ? C20 C21 C16 120.3(11) . . ? N2 C10 C9 121.7(11) . . ? N2 C10 C11 116.2(10) . . ? C9 C10 C11 122.1(11) . . ? S1 O3 Tb1 147.8(5) . 7 ? C22 O8 Tb1 118.7(8) . 7_556 ? O7 C22 O8 126.8(12) . . ? O7 C22 C22 115.6(14) . 7_556 ? O8 C22 C22 117.5(15) . 7_556 ? C10 C9 C8 120.2(11) . . ? C19 C18 C17 122.1(12) . . ? C8 C7 C6 120.3(12) . . ? N1 C5 C4 120.3(13) . . ? N1 C5 C6 117.8(11) . . ? C4 C5 C6 121.9(13) . . ? N3 C15 C14 124.3(13) . . ? N3 C11 C12 120.6(12) . . ? N3 C11 C10 116.0(11) . . ? C12 C11 C10 123.5(11) . . ? C7 C8 C9 117.1(11) . . ? C7 C8 C16 122.3(11) . . ? C9 C8 C16 120.5(11) . . ? C13 C12 C11 120.8(13) . . ? C5 C4 C3 121.4(15) . . ? C12 C13 C14 119.2(13) . . ? C13 C14 C15 118.3(13) . . ? N1 C1 C2 123.0(14) . . ? C1 C2 C3 120.5(15) . . ? C2 C3 C4 116.2(16) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.096 _refine_diff_density_min -0.817 _refine_diff_density_rms 0.202 _database_code_depnum_ccdc_archive 'CCDC 946686' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_11 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H14 Er N3 O9 S2' _chemical_formula_weight 695.74 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' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.010(3) _cell_length_b 18.516(2) _cell_length_c 13.7905(18) _cell_angle_alpha 90.00 _cell_angle_beta 117.896(2) _cell_angle_gamma 90.00 _cell_volume 4515.8(10) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.047 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2712 _exptl_absorpt_coefficient_mu 3.964 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5044 _exptl_absorpt_correction_T_max 0.5878 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10984 _diffrn_reflns_av_R_equivalents 0.0716 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 26.99 _reflns_number_total 4866 _reflns_number_gt 3081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4866 _refine_ls_number_parameters 334 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.092 _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 Er1 Er 0.14937(2) 0.18630(2) 0.27210(3) 0.02561(15) Uani 1 1 d . . . S2 S 0.04645(14) 0.11955(14) -0.60175(18) 0.0274(6) Uani 1 1 d . . . S1 S 0.19537(18) 0.2679(2) -0.2201(2) 0.0530(9) Uani 1 1 d . . . O4 O -0.0354(3) 0.1215(4) -0.6619(5) 0.0297(16) Uani 1 1 d . . . O7 O 0.1823(4) 0.2910(3) 0.3813(5) 0.0314(16) Uani 1 1 d . . . N2 N 0.1296(4) 0.1694(4) 0.0816(6) 0.0284(19) Uani 1 1 d . . . C19 C 0.0697(5) 0.1315(6) -0.4613(7) 0.027(2) Uani 1 1 d . . . C6 C 0.0950(6) 0.2210(6) 0.0055(8) 0.032(2) Uani 1 1 d . . . C16 C 0.1073(5) 0.1472(6) -0.2400(7) 0.028(2) Uani 1 1 d . . . N3 N 0.2000(4) 0.0730(5) 0.2424(6) 0.031(2) Uani 1 1 d . . . N1 N 0.0796(5) 0.2846(5) 0.1468(6) 0.036(2) Uani 1 1 d . . . O5 O 0.0788(4) 0.1812(4) -0.6309(5) 0.0417(19) Uani 1 1 d . . . C17 C 0.1307(5) 0.1980(5) -0.2931(7) 0.029(2) Uani 1 1 d . . . C20 C 0.0486(6) 0.0803(6) -0.4097(8) 0.038(3) Uani 1 1 d . . . H20A H 0.0221 0.0397 -0.4483 0.045 Uiso 1 1 calc R . . C21 C 0.0665(6) 0.0882(6) -0.2995(7) 0.035(3) Uani 1 1 d . . . H21A H 0.0508 0.0535 -0.2658 0.042 Uiso 1 1 calc R . . C10 C 0.1559(5) 0.1109(5) 0.0541(7) 0.024(2) Uani 1 1 d . . . O3 O 0.2411(4) 0.2738(4) -0.2760(5) 0.046(2) Uani 1 1 d . . . O8 O 0.2596(4) 0.3394(4) 0.5459(5) 0.0345(17) Uani 1 1 d . . . C22 C 0.2340(6) 0.2873(5) 0.4792(8) 0.034(3) Uani 1 1 d . . . C9 C 0.1506(5) 0.1026(5) -0.0490(7) 0.031(2) Uani 1 1 d . . . H9A H 0.1696 0.0615 -0.0663 0.037 Uiso 1 1 calc R . . O2 O 0.2387(6) 0.2446(7) -0.1102(6) 0.126(5) Uani 1 1 d . . . C18 C 0.1134(5) 0.1889(5) -0.4031(7) 0.030(2) Uani 1 1 d . . . H18A H 0.1315 0.2216 -0.4366 0.036 Uiso 1 1 calc R . . C7 C 0.0898(6) 0.2175(6) -0.0977(7) 0.033(2) Uani 1 1 d . . . H7A H 0.0688 0.2555 -0.1469 0.040 Uiso 1 1 calc R . . C5 C 0.0626(6) 0.2825(6) 0.0391(8) 0.036(3) Uani 1 1 d . . . C15 C 0.2381(7) 0.0269(6) 0.3257(8) 0.047(3) Uani 1 1 d . . . H15A H 0.2436 0.0383 0.3947 0.056 Uiso 1 1 calc R . . O6 O 0.0768(4) 0.0524(4) -0.6098(5) 0.050(2) Uani 1 1 d . . . C11 C 0.1946(5) 0.0561(5) 0.1413(7) 0.031(2) Uani 1 1 d . . . C8 C 0.1161(5) 0.1572(6) -0.1266(7) 0.029(2) Uani 1 1 d . . . O1 O 0.1503(6) 0.3298(6) -0.2317(11) 0.117(5) Uani 1 1 d . . . C12 C 0.2242(6) -0.0066(6) 0.1272(8) 0.037(3) Uani 1 1 d . . . H12A H 0.2183 -0.0172 0.0577 0.044 Uiso 1 1 calc R . . C4 C 0.0171(8) 0.3341(7) -0.0338(10) 0.065(4) Uani 1 1 d . . . H4A H 0.0069 0.3313 -0.1068 0.078 Uiso 1 1 calc R . . C13 C 0.2623(7) -0.0552(7) 0.2103(9) 0.055(3) Uani 1 1 d . . . H13A H 0.2821 -0.0978 0.1986 0.066 Uiso 1 1 calc R . . C14 C 0.2697(7) -0.0373(6) 0.3132(8) 0.051(3) Uani 1 1 d . . . H14A H 0.2955 -0.0678 0.3729 0.061 Uiso 1 1 calc R . . C1 C 0.0532(7) 0.3410(7) 0.1792(10) 0.056(3) Uani 1 1 d . . . H1A H 0.0673 0.3448 0.2535 0.067 Uiso 1 1 calc R . . C2 C 0.0064(8) 0.3941(7) 0.1099(11) 0.066(4) Uani 1 1 d . . . H2A H -0.0114 0.4315 0.1365 0.080 Uiso 1 1 calc R . . C3 C -0.0132(10) 0.3894(8) -0.0018(12) 0.092(6) Uani 1 1 d . . . H3A H -0.0458 0.4228 -0.0522 0.111 Uiso 1 1 calc R . . O1W O 0.3348(15) -0.1123(15) 0.545(2) 0.139(9) Uani 0.50 1 d PU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Er1 0.0307(3) 0.0314(3) 0.0169(2) -0.0039(2) 0.01295(19) -0.0060(2) S2 0.0283(14) 0.0397(15) 0.0164(11) -0.0025(10) 0.0122(11) 0.0012(12) S1 0.057(2) 0.074(2) 0.0416(17) -0.0288(16) 0.0341(17) -0.0384(19) O4 0.027(4) 0.047(4) 0.016(3) 0.003(3) 0.010(3) 0.005(3) O7 0.040(4) 0.025(4) 0.023(4) -0.005(3) 0.010(3) -0.004(3) N2 0.027(5) 0.044(6) 0.014(4) -0.003(4) 0.009(4) -0.004(4) C19 0.018(5) 0.044(6) 0.014(4) -0.005(4) 0.005(4) -0.004(5) C6 0.031(6) 0.044(7) 0.025(5) -0.006(5) 0.016(5) -0.009(5) C16 0.026(5) 0.045(7) 0.017(5) -0.009(4) 0.013(4) -0.010(5) N3 0.029(5) 0.041(5) 0.026(4) 0.000(4) 0.015(4) -0.007(4) N1 0.046(6) 0.042(5) 0.025(4) -0.005(4) 0.021(4) -0.009(5) O5 0.053(5) 0.058(5) 0.026(4) -0.008(3) 0.028(4) -0.020(4) C17 0.023(5) 0.048(7) 0.018(5) -0.006(4) 0.010(4) -0.002(5) C20 0.050(7) 0.037(7) 0.029(5) -0.018(5) 0.021(5) -0.017(5) C21 0.043(7) 0.046(7) 0.022(5) -0.008(5) 0.022(5) -0.011(6) C10 0.029(5) 0.027(5) 0.016(4) -0.006(4) 0.010(4) -0.011(4) O3 0.044(5) 0.069(6) 0.035(4) -0.015(4) 0.026(4) -0.034(4) O8 0.043(4) 0.035(4) 0.022(4) -0.007(3) 0.013(3) -0.008(3) C22 0.038(7) 0.043(7) 0.026(5) -0.004(5) 0.018(5) -0.007(5) C9 0.031(6) 0.034(6) 0.027(5) -0.004(4) 0.014(5) -0.002(5) O2 0.122(9) 0.219(14) 0.027(5) -0.032(7) 0.027(6) -0.135(10) C18 0.034(6) 0.037(6) 0.025(5) 0.002(5) 0.020(5) -0.004(5) C7 0.041(7) 0.038(6) 0.024(5) -0.003(4) 0.018(5) -0.004(5) C5 0.051(7) 0.037(6) 0.027(5) 0.001(5) 0.025(5) -0.003(5) C15 0.078(9) 0.036(7) 0.025(6) -0.005(5) 0.023(6) -0.003(6) O6 0.049(5) 0.063(6) 0.025(4) -0.004(4) 0.006(4) 0.024(4) C11 0.035(6) 0.034(6) 0.026(5) -0.009(5) 0.017(5) -0.008(5) C8 0.025(5) 0.040(6) 0.020(5) -0.008(4) 0.008(4) -0.013(5) O1 0.093(9) 0.079(8) 0.198(14) -0.074(8) 0.085(9) -0.040(7) C12 0.051(7) 0.038(7) 0.021(5) -0.009(5) 0.017(5) 0.002(6) C4 0.100(12) 0.051(9) 0.040(7) 0.016(6) 0.030(8) 0.028(8) C13 0.064(9) 0.054(8) 0.053(8) -0.015(7) 0.033(7) 0.006(7) C14 0.071(9) 0.037(7) 0.026(6) 0.009(5) 0.007(6) 0.009(6) C1 0.062(9) 0.069(9) 0.036(6) -0.010(6) 0.022(7) 0.016(8) C2 0.084(11) 0.054(9) 0.065(9) 0.003(7) 0.038(8) 0.031(8) C3 0.132(15) 0.093(13) 0.060(9) 0.021(9) 0.052(10) 0.055(11) O1W 0.143(12) 0.154(13) 0.143(12) 0.029(9) 0.085(9) 0.003(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 Er1 O3 2.291(6) 7 ? Er1 O7 2.352(6) . ? Er1 O5 2.358(6) 1_556 ? Er1 O8 2.360(6) 7_556 ? Er1 O4 2.389(6) 2_554 ? Er1 N1 2.447(9) . ? Er1 N3 2.447(8) . ? Er1 N2 2.487(7) . ? S2 O6 1.411(7) . ? S2 O4 1.449(6) . ? S2 O5 1.459(7) . ? S2 C19 1.782(8) . ? S1 O2 1.417(10) . ? S1 O1 1.420(11) . ? S1 O3 1.449(7) . ? S1 C17 1.774(10) . ? O4 Er1 2.389(6) 2_554 ? O7 C22 1.261(11) . ? N2 C10 1.334(11) . ? N2 C6 1.347(12) . ? C19 C18 1.372(13) . ? C19 C20 1.365(13) . ? C6 C7 1.379(12) . ? C6 C5 1.487(14) . ? C16 C21 1.380(13) . ? C16 C17 1.400(13) . ? C16 C8 1.501(11) . ? N3 C15 1.344(12) . ? N3 C11 1.383(11) . ? N1 C1 1.338(13) . ? N1 C5 1.360(11) . ? O5 Er1 2.358(6) 1_554 ? C17 C18 1.400(11) . ? C20 C21 1.396(12) . ? C10 C9 1.384(12) . ? C10 C11 1.486(13) . ? O3 Er1 2.291(6) 7 ? O8 C22 1.266(11) . ? O8 Er1 2.360(6) 7_556 ? C22 C22 1.52(2) 7_556 ? C9 C8 1.397(13) . ? C7 C8 1.371(13) . ? C5 C4 1.377(14) . ? C15 C14 1.394(14) . ? C11 C12 1.358(13) . ? C12 C13 1.373(15) . ? C4 C3 1.365(17) . ? C13 C14 1.397(14) . ? C1 C2 1.385(15) . ? C2 C3 1.402(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Er1 O7 75.0(2) 7 . ? O3 Er1 O5 145.1(2) 7 1_556 ? O7 Er1 O5 74.5(2) . 1_556 ? O3 Er1 O8 77.6(2) 7 7_556 ? O7 Er1 O8 68.9(2) . 7_556 ? O5 Er1 O8 76.0(2) 1_556 7_556 ? O3 Er1 O4 142.7(2) 7 2_554 ? O7 Er1 O4 136.0(2) . 2_554 ? O5 Er1 O4 72.1(2) 1_556 2_554 ? O8 Er1 O4 127.4(2) 7_556 2_554 ? O3 Er1 N1 90.0(3) 7 . ? O7 Er1 N1 74.7(2) . . ? O5 Er1 N1 97.8(3) 1_556 . ? O8 Er1 N1 143.4(3) 7_556 . ? O4 Er1 N1 82.2(2) 2_554 . ? O3 Er1 N3 79.3(3) 7 . ? O7 Er1 N3 143.1(2) . . ? O5 Er1 N3 117.7(2) 1_556 . ? O8 Er1 N3 80.2(2) 7_556 . ? O4 Er1 N3 79.1(2) 2_554 . ? N1 Er1 N3 131.6(3) . . ? O3 Er1 N2 75.1(2) 7 . ? O7 Er1 N2 129.7(2) . . ? O5 Er1 N2 138.8(2) 1_556 . ? O8 Er1 N2 139.5(2) 7_556 . ? O4 Er1 N2 68.5(2) 2_554 . ? N1 Er1 N2 65.9(3) . . ? N3 Er1 N2 65.7(3) . . ? O6 S2 O4 112.9(4) . . ? O6 S2 O5 114.0(5) . . ? O4 S2 O5 110.5(4) . . ? O6 S2 C19 106.9(4) . . ? O4 S2 C19 105.7(4) . . ? O5 S2 C19 106.2(4) . . ? O2 S1 O1 113.9(8) . . ? O2 S1 O3 111.7(6) . . ? O1 S1 O3 113.9(7) . . ? O2 S1 C17 107.7(5) . . ? O1 S1 C17 105.6(5) . . ? O3 S1 C17 103.2(4) . . ? S2 O4 Er1 149.8(4) . 2_554 ? C22 O7 Er1 118.9(6) . . ? C10 N2 C6 118.8(8) . . ? C10 N2 Er1 120.9(6) . . ? C6 N2 Er1 120.2(6) . . ? C18 C19 C20 120.1(8) . . ? C18 C19 S2 120.1(7) . . ? C20 C19 S2 119.6(7) . . ? N2 C6 C7 122.2(9) . . ? N2 C6 C5 116.2(8) . . ? C7 C6 C5 121.6(10) . . ? C21 C16 C17 118.1(8) . . ? C21 C16 C8 117.7(8) . . ? C17 C16 C8 123.8(8) . . ? C15 N3 C11 117.6(9) . . ? C15 N3 Er1 121.0(6) . . ? C11 N3 Er1 121.3(6) . . ? C1 N1 C5 116.8(9) . . ? C1 N1 Er1 121.9(7) . . ? C5 N1 Er1 121.3(7) . . ? S2 O5 Er1 130.4(4) . 1_554 ? C16 C17 C18 120.8(9) . . ? C16 C17 S1 121.9(7) . . ? C18 C17 S1 116.6(7) . . ? C19 C20 C21 120.6(9) . . ? C16 C21 C20 120.6(9) . . ? N2 C10 C9 122.1(9) . . ? N2 C10 C11 116.8(8) . . ? C9 C10 C11 121.1(9) . . ? S1 O3 Er1 147.9(4) . 7 ? C22 O8 Er1 117.9(6) . 7_556 ? O7 C22 O8 125.9(9) . . ? O7 C22 C22 116.4(11) . 7_556 ? O8 C22 C22 117.6(11) . 7_556 ? C10 C9 C8 118.7(9) . . ? C19 C18 C17 119.6(9) . . ? C8 C7 C6 119.0(10) . . ? N1 C5 C4 121.3(10) . . ? N1 C5 C6 116.0(9) . . ? C4 C5 C6 122.6(9) . . ? N3 C15 C14 123.0(9) . . ? C12 C11 N3 120.3(9) . . ? C12 C11 C10 124.4(8) . . ? N3 C11 C10 115.3(8) . . ? C7 C8 C9 119.0(9) . . ? C7 C8 C16 122.0(9) . . ? C9 C8 C16 118.9(9) . . ? C13 C12 C11 123.4(9) . . ? C3 C4 C5 121.8(12) . . ? C12 C13 C14 116.5(11) . . ? C13 C14 C15 119.3(10) . . ? N1 C1 C2 124.7(11) . . ? C1 C2 C3 117.7(12) . . ? C4 C3 C2 117.6(13) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 2.023 _refine_diff_density_min -0.938 _refine_diff_density_rms 0.214 _database_code_depnum_ccdc_archive 'CCDC 946689' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 N3 O9 S2 Yb' _chemical_formula_weight 702.53 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.952(7) _cell_length_b 18.500(6) _cell_length_c 13.756(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.935(4) _cell_angle_gamma 90.00 _cell_volume 4486(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.080 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2736 _exptl_absorpt_coefficient_mu 4.419 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3507 _exptl_absorpt_correction_T_max 0.4046 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12818 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.0847 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4880 _reflns_number_gt 3330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4880 _refine_ls_number_parameters 334 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1197 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.043 _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 Yb1 Yb 0.14981(2) 0.187055(18) 0.27241(2) 0.02514(13) Uani 1 1 d . . . S2 S 0.04634(12) 0.11977(11) -0.60227(14) 0.0261(4) Uani 1 1 d . . . S1 S 0.19541(16) 0.26846(16) -0.2193(2) 0.0541(8) Uani 1 1 d . . . O4 O -0.0358(3) 0.1230(3) -0.6628(4) 0.0316(13) Uani 1 1 d . . . O7 O 0.1824(4) 0.2918(3) 0.3815(4) 0.0360(14) Uani 1 1 d . . . N2 N 0.1295(4) 0.1705(3) 0.0838(5) 0.0242(15) Uani 1 1 d . . . C19 C 0.0697(4) 0.1321(4) -0.4622(6) 0.0262(17) Uani 1 1 d . . . C6 C 0.0944(5) 0.2208(4) 0.0059(6) 0.0289(18) Uani 1 1 d . . . C16 C 0.1065(5) 0.1483(4) -0.2414(6) 0.0283(19) Uani 1 1 d . . . N3 N 0.2000(4) 0.0730(4) 0.2445(5) 0.0307(16) Uani 1 1 d . . . N1 N 0.0797(4) 0.2847(4) 0.1477(5) 0.0342(17) Uani 1 1 d . . . O5 O 0.0796(4) 0.1818(3) -0.6310(4) 0.0398(15) Uani 1 1 d . . . C17 C 0.1322(5) 0.1982(4) -0.2920(6) 0.033(2) Uani 1 1 d . . . C20 C 0.0482(5) 0.0804(5) -0.4092(6) 0.039(2) Uani 1 1 d . . . H20A H 0.0208 0.0402 -0.4481 0.047 Uiso 1 1 calc R . . C21 C 0.0665(5) 0.0878(4) -0.3011(6) 0.031(2) Uani 1 1 d . . . H21A H 0.0523 0.0522 -0.2666 0.037 Uiso 1 1 calc R . . C10 C 0.1560(5) 0.1110(4) 0.0567(6) 0.0276(18) Uani 1 1 d . . . O3 O 0.2418(4) 0.2754(4) -0.2751(5) 0.0461(16) Uani 1 1 d U . . O8 O 0.2593(3) 0.3392(3) 0.5467(4) 0.0349(14) Uani 1 1 d . . . C22 C 0.2328(5) 0.2879(4) 0.4794(7) 0.034(2) Uani 1 1 d . . . C9 C 0.1506(5) 0.1029(5) -0.0474(6) 0.033(2) Uani 1 1 d . . . H9A H 0.1690 0.0613 -0.0648 0.040 Uiso 1 1 calc R . . O2 O 0.2392(5) 0.2432(5) -0.1097(6) 0.101(3) Uani 1 1 d U . . C18 C 0.1122(5) 0.1900(4) -0.4022(6) 0.0291(19) Uani 1 1 d . . . H18A H 0.1279 0.2244 -0.4365 0.035 Uiso 1 1 calc R . . C7 C 0.0889(5) 0.2163(4) -0.0986(6) 0.0281(18) Uani 1 1 d . . . H7A H 0.0659 0.2531 -0.1496 0.034 Uiso 1 1 calc R . . C5 C 0.0631(5) 0.2831(4) 0.0417(6) 0.032(2) Uani 1 1 d . . . C15 C 0.2378(6) 0.0270(5) 0.3270(7) 0.043(2) Uani 1 1 d . . . H15A H 0.2436 0.0387 0.3962 0.052 Uiso 1 1 calc R . . O6 O 0.0767(4) 0.0516(3) -0.6102(4) 0.0480(18) Uani 1 1 d . . . C11 C 0.1943(4) 0.0563(4) 0.1446(6) 0.0264(17) Uani 1 1 d . . . C8 C 0.1175(5) 0.1572(5) -0.1250(6) 0.0298(19) Uani 1 1 d . . . O1 O 0.1511(6) 0.3302(5) -0.2282(10) 0.132(5) Uani 1 1 d . . . C12 C 0.2227(5) -0.0056(5) 0.1283(7) 0.045(2) Uani 1 1 d . . . H12A H 0.2160 -0.0168 0.0584 0.053 Uiso 1 1 calc R . . C4 C 0.0177(7) 0.3348(6) -0.0324(9) 0.066(4) Uani 1 1 d . . . H4A H 0.0082 0.3323 -0.1053 0.079 Uiso 1 1 calc R . . C13 C 0.2623(6) -0.0538(5) 0.2155(7) 0.046(2) Uani 1 1 d . . . H13A H 0.2835 -0.0960 0.2052 0.055 Uiso 1 1 calc R . . C14 C 0.2687(6) -0.0366(5) 0.3156(7) 0.051(3) Uani 1 1 d . . . H14 H 0.2936 -0.0675 0.3753 0.061 Uiso 1 1 calc R . . C1 C 0.0524(6) 0.3397(5) 0.1807(8) 0.053(3) Uani 1 1 d . . . H1A H 0.0644 0.3418 0.2546 0.063 Uiso 1 1 calc R . . C2 C 0.0076(8) 0.3936(6) 0.1127(9) 0.073(4) Uani 1 1 d . . . H2A H -0.0084 0.4319 0.1405 0.088 Uiso 1 1 calc R . . C3 C -0.0133(8) 0.3894(6) -0.0001(9) 0.079(4) Uani 1 1 d . . . H3A H -0.0469 0.4224 -0.0504 0.095 Uiso 1 1 calc R . . O1W O 0.098(2) 0.4354(14) -0.152(3) 0.70(2) Uani 1 1 d . . . H1WA H 0.0897 0.4261 -0.2164 1.044 Uiso 1 1 d R . . H1WB H 0.1212 0.4031 -0.1117 1.044 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Yb1 0.0298(2) 0.0315(2) 0.01659(18) -0.00386(14) 0.01299(15) -0.00572(16) S2 0.0258(11) 0.0385(12) 0.0146(9) -0.0032(8) 0.0099(8) 0.0004(9) S1 0.0586(18) 0.080(2) 0.0403(14) -0.0316(13) 0.0371(14) -0.0420(15) O4 0.028(3) 0.045(4) 0.020(3) 0.002(2) 0.010(3) 0.005(3) O7 0.044(4) 0.036(3) 0.023(3) 0.000(2) 0.012(3) -0.005(3) N2 0.028(4) 0.028(4) 0.019(3) -0.004(3) 0.013(3) -0.008(3) C19 0.025(4) 0.036(5) 0.021(4) -0.003(3) 0.013(4) -0.007(4) C6 0.027(5) 0.038(5) 0.029(4) -0.003(4) 0.019(4) -0.003(4) C16 0.030(5) 0.041(5) 0.019(4) -0.006(3) 0.016(4) -0.009(4) N3 0.033(4) 0.042(4) 0.018(3) -0.001(3) 0.013(3) 0.000(3) N1 0.038(5) 0.046(4) 0.021(4) -0.008(3) 0.016(3) 0.002(3) O5 0.043(4) 0.062(4) 0.025(3) -0.008(3) 0.025(3) -0.015(3) C17 0.037(5) 0.044(5) 0.024(4) -0.016(4) 0.019(4) -0.016(4) C20 0.056(6) 0.039(5) 0.022(4) -0.016(4) 0.017(4) -0.019(4) C21 0.046(6) 0.028(4) 0.027(4) -0.005(3) 0.024(4) -0.013(4) C10 0.028(5) 0.031(5) 0.025(4) -0.007(3) 0.013(4) -0.011(4) O3 0.041(4) 0.071(4) 0.036(3) -0.014(3) 0.026(3) -0.023(3) O8 0.045(4) 0.032(3) 0.029(3) -0.007(2) 0.018(3) -0.010(3) C22 0.038(6) 0.042(5) 0.025(4) -0.004(4) 0.018(4) -0.011(4) C9 0.039(5) 0.043(5) 0.021(4) -0.006(4) 0.016(4) -0.004(4) O2 0.099(6) 0.159(7) 0.041(4) -0.006(4) 0.029(4) -0.076(5) C18 0.034(5) 0.037(5) 0.021(4) -0.006(3) 0.017(4) -0.012(4) C7 0.030(5) 0.034(5) 0.024(4) 0.005(3) 0.015(4) -0.005(4) C5 0.045(6) 0.029(4) 0.024(4) 0.007(3) 0.018(4) -0.003(4) C15 0.061(7) 0.041(6) 0.037(5) -0.004(4) 0.030(5) 0.001(5) O6 0.050(4) 0.065(5) 0.020(3) -0.004(3) 0.009(3) 0.024(3) C11 0.023(4) 0.034(5) 0.025(4) -0.003(3) 0.014(4) -0.005(4) C8 0.028(5) 0.041(5) 0.022(4) -0.008(4) 0.013(4) -0.014(4) O1 0.123(9) 0.080(6) 0.248(14) -0.111(8) 0.133(10) -0.060(6) C12 0.044(6) 0.059(7) 0.027(5) -0.008(4) 0.014(5) -0.005(5) C4 0.107(11) 0.063(7) 0.047(6) 0.012(5) 0.053(7) 0.031(7) C13 0.053(7) 0.041(6) 0.036(5) -0.010(4) 0.015(5) 0.010(5) C14 0.069(8) 0.042(6) 0.033(5) 0.003(4) 0.016(5) 0.007(5) C1 0.074(8) 0.053(6) 0.039(6) 0.002(5) 0.033(6) 0.012(6) C2 0.132(12) 0.046(7) 0.060(7) 0.000(5) 0.061(8) 0.026(7) C3 0.121(12) 0.073(8) 0.047(7) 0.014(6) 0.042(8) 0.042(8) O1W 1.06(6) 0.45(3) 1.24(7) -0.57(2) 1.09(6) -0.501 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Yb1 O3 2.255(6) 7 ? Yb1 O5 2.341(5) 1_556 ? Yb1 O8 2.343(6) 7_556 ? Yb1 O7 2.348(5) . ? Yb1 O4 2.374(5) 2_554 ? Yb1 N1 2.432(7) . ? Yb1 N3 2.442(7) . ? Yb1 N2 2.450(6) . ? Yb1 C22 3.141(9) 7_556 ? Yb1 C22 3.149(8) . ? S2 O6 1.425(6) . ? S2 O4 1.451(6) . ? S2 O5 1.469(6) . ? S2 C19 1.772(7) . ? S1 O1 1.415(10) . ? S1 O2 1.422(8) . ? S1 O3 1.459(6) . ? S1 C17 1.759(8) . ? O4 Yb1 2.374(5) 2_554 ? O7 C22 1.250(10) . ? N2 C10 1.347(10) . ? N2 C6 1.343(10) . ? C19 C18 1.375(10) . ? C19 C20 1.387(11) . ? C6 C7 1.391(10) . ? C6 C5 1.500(11) . ? C16 C17 1.391(11) . ? C16 C21 1.396(10) . ? C16 C8 1.520(10) . ? N3 C15 1.334(10) . ? N3 C11 1.360(9) . ? N1 C5 1.335(9) . ? N1 C1 1.332(11) . ? O5 Yb1 2.341(5) 1_554 ? C17 C18 1.384(10) . ? C20 C21 1.363(10) . ? C10 C9 1.393(10) . ? C10 C11 1.485(11) . ? O3 Yb1 2.255(6) 7 ? O8 C22 1.255(9) . ? O8 Yb1 2.343(6) 7_556 ? C22 C22 1.548(17) 7_556 ? C22 Yb1 3.141(9) 7_556 ? C9 C8 1.388(11) . ? C7 C8 1.359(11) . ? C5 C4 1.382(13) . ? C15 C14 1.370(12) . ? C11 C12 1.342(11) . ? C12 C13 1.403(12) . ? C4 C3 1.363(14) . ? C13 C14 1.359(12) . ? C1 C2 1.372(13) . ? C2 C3 1.408(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Yb1 O5 145.9(2) 7 1_556 ? O3 Yb1 O8 77.7(2) 7 7_556 ? O5 Yb1 O8 76.1(2) 1_556 7_556 ? O3 Yb1 O7 76.1(2) 7 . ? O5 Yb1 O7 74.4(2) 1_556 . ? O8 Yb1 O7 69.34(19) 7_556 . ? O3 Yb1 O4 142.20(18) 7 2_554 ? O5 Yb1 O4 71.91(18) 1_556 2_554 ? O8 Yb1 O4 127.27(18) 7_556 2_554 ? O7 Yb1 O4 135.5(2) . 2_554 ? O3 Yb1 N1 90.8(2) 7 . ? O5 Yb1 N1 97.6(2) 1_556 . ? O8 Yb1 N1 143.8(2) 7_556 . ? O7 Yb1 N1 74.6(2) . . ? O4 Yb1 N1 81.9(2) 2_554 . ? O3 Yb1 N3 78.9(2) 7 . ? O5 Yb1 N3 116.8(2) 1_556 . ? O8 Yb1 N3 79.5(2) 7_556 . ? O7 Yb1 N3 143.4(2) . . ? O4 Yb1 N3 79.1(2) 2_554 . ? N1 Yb1 N3 132.3(2) . . ? O3 Yb1 N2 74.8(2) 7 . ? O5 Yb1 N2 138.5(2) 1_556 . ? O8 Yb1 N2 139.5(2) 7_556 . ? O7 Yb1 N2 129.73(19) . . ? O4 Yb1 N2 68.35(19) 2_554 . ? N1 Yb1 N2 65.8(2) . . ? N3 Yb1 N2 66.5(2) . . ? O3 Yb1 C22 73.5(2) 7 7_556 ? O5 Yb1 C22 74.3(2) 1_556 7_556 ? O8 Yb1 C22 20.6(2) 7_556 7_556 ? O7 Yb1 C22 48.8(2) . 7_556 ? O4 Yb1 C22 140.21(19) 2_554 7_556 ? N1 Yb1 C22 123.2(2) . 7_556 ? N3 Yb1 C22 98.4(2) . 7_556 ? N2 Yb1 C22 147.0(2) . 7_556 ? O3 Yb1 C22 73.1(2) 7 . ? O5 Yb1 C22 73.3(2) 1_556 . ? O8 Yb1 C22 49.0(2) 7_556 . ? O7 Yb1 C22 20.3(2) . . ? O4 Yb1 C22 144.2(2) 2_554 . ? N1 Yb1 C22 94.8(2) . . ? N3 Yb1 C22 125.0(2) . . ? N2 Yb1 C22 142.0(2) . . ? C22 Yb1 C22 28.5(3) 7_556 . ? O6 S2 O4 113.5(4) . . ? O6 S2 O5 114.1(4) . . ? O4 S2 O5 110.1(3) . . ? O6 S2 C19 107.0(4) . . ? O4 S2 C19 105.7(3) . . ? O5 S2 C19 105.7(3) . . ? O1 S1 O2 113.9(6) . . ? O1 S1 O3 114.1(6) . . ? O2 S1 O3 111.2(5) . . ? O1 S1 C17 107.1(5) . . ? O2 S1 C17 106.3(5) . . ? O3 S1 C17 103.2(4) . . ? S2 O4 Yb1 150.9(3) . 2_554 ? C22 O7 Yb1 118.9(5) . . ? C10 N2 C6 118.1(6) . . ? C10 N2 Yb1 120.3(5) . . ? C6 N2 Yb1 121.6(5) . . ? C18 C19 C20 118.5(7) . . ? C18 C19 S2 121.8(6) . . ? C20 C19 S2 119.6(6) . . ? N2 C6 C7 122.9(7) . . ? N2 C6 C5 114.3(6) . . ? C7 C6 C5 122.8(7) . . ? C17 C16 C21 118.8(7) . . ? C17 C16 C8 123.4(7) . . ? C21 C16 C8 117.8(7) . . ? C15 N3 C11 117.4(7) . . ? C15 N3 Yb1 121.9(5) . . ? C11 N3 Yb1 120.6(5) . . ? C5 N1 C1 117.2(8) . . ? C5 N1 Yb1 121.4(6) . . ? C1 N1 Yb1 121.3(6) . . ? S2 O5 Yb1 130.6(3) . 1_554 ? C18 C17 C16 119.4(7) . . ? C18 C17 S1 117.8(6) . . ? C16 C17 S1 122.7(6) . . ? C21 C20 C19 120.9(7) . . ? C20 C21 C16 120.7(7) . . ? N2 C10 C9 121.4(7) . . ? N2 C10 C11 116.7(6) . . ? C9 C10 C11 121.8(7) . . ? S1 O3 Yb1 149.1(4) . 7 ? C22 O8 Yb1 118.4(6) . 7_556 ? O7 C22 O8 126.8(8) . . ? O7 C22 C22 116.2(9) . 7_556 ? O8 C22 C22 117.0(9) . 7_556 ? O7 C22 Yb1 167.7(6) . 7_556 ? O8 C22 Yb1 41.0(4) . 7_556 ? C22 C22 Yb1 76.1(6) 7_556 7_556 ? O7 C22 Yb1 40.7(4) . . ? O8 C22 Yb1 167.3(6) . . ? C22 C22 Yb1 75.5(6) 7_556 . ? Yb1 C22 Yb1 151.5(3) 7_556 . ? C10 C9 C8 119.5(8) . . ? C19 C18 C17 121.6(7) . . ? C8 C7 C6 119.0(7) . . ? N1 C5 C4 122.1(8) . . ? N1 C5 C6 116.5(7) . . ? C4 C5 C6 121.3(7) . . ? N3 C15 C14 123.8(8) . . ? C12 C11 N3 121.4(7) . . ? C12 C11 C10 122.8(7) . . ? N3 C11 C10 115.8(7) . . ? C7 C8 C9 119.0(7) . . ? C7 C8 C16 119.8(7) . . ? C9 C8 C16 120.9(7) . . ? C11 C12 C13 120.7(8) . . ? C3 C4 C5 120.9(9) . . ? C14 C13 C12 117.8(9) . . ? C13 C14 C15 118.8(9) . . ? N1 C1 C2 124.2(9) . . ? C1 C2 C3 118.4(10) . . ? C4 C3 C2 116.9(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.562 _refine_diff_density_min -1.196 _refine_diff_density_rms 0.197 _database_code_depnum_ccdc_archive 'CCDC 946690' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_13 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 Lu N3 O9 S2' _chemical_formula_weight 704.46 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' Lu Lu -0.4720 5.8584 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.858(3) _cell_length_b 18.452(2) _cell_length_c 13.7432(18) _cell_angle_alpha 90.00 _cell_angle_beta 118.078(2) _cell_angle_gamma 90.00 _cell_volume 4443.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1446 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 20.80 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.106 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2744 _exptl_absorpt_coefficient_mu 4.695 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3064 _exptl_absorpt_correction_T_max 0.3531 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13097 _diffrn_reflns_av_R_equivalents 0.0695 _diffrn_reflns_av_sigmaI/netI 0.0873 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4828 _reflns_number_gt 3262 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4828 _refine_ls_number_parameters 334 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1115 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.027 _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 Lu1 Lu 0.150250(19) 0.187188(18) 0.27257(3) 0.02385(12) Uani 1 1 d . . . S2 S 0.04618(11) 0.11987(11) -0.60280(16) 0.0258(5) Uani 1 1 d . . . S1 S 0.19562(16) 0.26840(17) -0.2183(2) 0.0539(8) Uani 1 1 d . . . O4 O -0.0365(3) 0.1227(3) -0.6639(4) 0.0284(13) Uani 1 1 d . . . O7 O 0.1825(3) 0.2922(3) 0.3802(4) 0.0298(13) Uani 1 1 d . . . N2 N 0.1298(4) 0.1696(4) 0.0845(5) 0.0260(15) Uani 1 1 d . . . C19 C 0.0694(4) 0.1310(4) -0.4625(6) 0.0236(17) Uani 1 1 d . . . C6 C 0.0950(5) 0.2211(5) 0.0073(7) 0.0299(19) Uani 1 1 d . . . C16 C 0.1076(5) 0.1476(5) -0.2400(7) 0.0297(19) Uani 1 1 d . . . N3 N 0.2001(4) 0.0731(3) 0.2465(5) 0.0277(15) Uani 1 1 d . . . N1 N 0.0794(4) 0.2858(4) 0.1486(6) 0.0339(17) Uani 1 1 d . . . O5 O 0.0802(3) 0.1821(3) -0.6306(5) 0.0392(15) Uani 1 1 d . . . C17 C 0.1310(5) 0.1972(5) -0.2933(7) 0.033(2) Uani 1 1 d . . . C20 C 0.0487(5) 0.0795(4) -0.4104(7) 0.033(2) Uani 1 1 d . . . H20A H 0.0223 0.0385 -0.4488 0.040 Uiso 1 1 calc R . . C21 C 0.0672(5) 0.0880(5) -0.2994(7) 0.037(2) Uani 1 1 d . . . H21A H 0.0521 0.0529 -0.2651 0.044 Uiso 1 1 calc R . . C10 C 0.1567(4) 0.1109(4) 0.0569(6) 0.0243(18) Uani 1 1 d . . . O3 O 0.2409(3) 0.2755(4) -0.2752(5) 0.0460(17) Uani 1 1 d . . . O8 O 0.2585(3) 0.3391(3) 0.5475(5) 0.0349(14) Uani 1 1 d . . . C22 C 0.2334(5) 0.2881(4) 0.4800(7) 0.0287(19) Uani 1 1 d . . . C9 C 0.1503(5) 0.1030(5) -0.0479(7) 0.030(2) Uani 1 1 d . . . H9A H 0.1687 0.0614 -0.0657 0.036 Uiso 1 1 calc R . . O2 O 0.2403(5) 0.2420(5) -0.1090(7) 0.099(3) Uani 1 1 d U . . C18 C 0.1122(4) 0.1900(4) -0.4032(6) 0.0281(18) Uani 1 1 d . . . H18A H 0.1282 0.2245 -0.4372 0.034 Uiso 1 1 calc R . . C7 C 0.0888(5) 0.2162(5) -0.0973(6) 0.031(2) Uani 1 1 d . . . H7A H 0.0657 0.2532 -0.1483 0.038 Uiso 1 1 calc R . . C5 C 0.0630(5) 0.2835(5) 0.0418(7) 0.035(2) Uani 1 1 d . . . C15 C 0.2384(5) 0.0259(5) 0.3296(7) 0.040(2) Uani 1 1 d . . . H15A H 0.2435 0.0372 0.3987 0.048 Uiso 1 1 calc R . . O6 O 0.0771(4) 0.0518(3) -0.6098(5) 0.0477(17) Uani 1 1 d . . . C11 C 0.1955(4) 0.0557(4) 0.1464(7) 0.0283(18) Uani 1 1 d . . . C8 C 0.1167(5) 0.1571(5) -0.1248(6) 0.0276(19) Uani 1 1 d . . . O1 O 0.1522(6) 0.3298(5) -0.2252(11) 0.137(5) Uani 1 1 d . . . C12 C 0.2244(5) -0.0082(5) 0.1313(7) 0.038(2) Uani 1 1 d . . . H12A H 0.2180 -0.0200 0.0616 0.046 Uiso 1 1 calc R . . C4 C 0.0172(7) 0.3355(5) -0.0336(8) 0.056(3) Uani 1 1 d . . . H4A H 0.0057 0.3327 -0.1074 0.067 Uiso 1 1 calc R . . C13 C 0.2626(5) -0.0548(5) 0.2172(8) 0.045(2) Uani 1 1 d . . . H13A H 0.2831 -0.0977 0.2072 0.054 Uiso 1 1 calc R . . C14 C 0.2699(6) -0.0366(5) 0.3191(9) 0.052(3) Uani 1 1 d . . . H14A H 0.2959 -0.0669 0.3795 0.063 Uiso 1 1 calc R . . C1 C 0.0516(6) 0.3420(5) 0.1821(9) 0.053(3) Uani 1 1 d . . . H1A H 0.0641 0.3453 0.2562 0.064 Uiso 1 1 calc R . . C2 C 0.0058(7) 0.3942(6) 0.1111(9) 0.067(4) Uani 1 1 d . . . H2A H -0.0139 0.4312 0.1362 0.081 Uiso 1 1 calc R . . C3 C -0.0106(8) 0.3914(6) 0.0038(10) 0.082(4) Uani 1 1 d . . . H3A H -0.0407 0.4272 -0.0448 0.099 Uiso 1 1 calc R . . O1W O 0.0960(18) 0.4373(12) -0.157(3) 0.49(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 Lu1 0.0296(2) 0.0296(2) 0.01552(18) -0.00366(15) 0.01324(14) -0.00532(17) S2 0.0281(11) 0.0373(12) 0.0140(10) -0.0028(8) 0.0115(9) 0.0000(9) S1 0.0597(17) 0.078(2) 0.0397(16) -0.0328(14) 0.0363(14) -0.0423(16) O4 0.027(3) 0.042(3) 0.017(3) 0.004(2) 0.010(2) 0.002(3) O7 0.036(3) 0.031(3) 0.018(3) -0.005(2) 0.008(3) -0.006(3) N2 0.021(3) 0.038(4) 0.017(4) -0.003(3) 0.007(3) -0.006(3) C19 0.025(4) 0.033(5) 0.013(4) -0.003(3) 0.009(3) -0.004(4) C6 0.027(4) 0.040(5) 0.029(5) -0.001(4) 0.018(4) -0.011(4) C16 0.035(5) 0.037(5) 0.024(5) -0.002(4) 0.020(4) -0.003(4) N3 0.035(4) 0.030(4) 0.019(4) -0.005(3) 0.013(3) -0.005(3) N1 0.042(4) 0.045(4) 0.017(4) -0.001(3) 0.015(3) -0.003(4) O5 0.050(4) 0.054(4) 0.023(3) -0.011(3) 0.025(3) -0.022(3) C17 0.031(5) 0.052(6) 0.021(5) -0.009(4) 0.017(4) -0.011(4) C20 0.050(5) 0.032(5) 0.025(5) -0.016(4) 0.022(4) -0.013(4) C21 0.053(6) 0.039(5) 0.026(5) -0.007(4) 0.024(5) -0.012(4) C10 0.020(4) 0.034(5) 0.025(5) -0.002(3) 0.016(4) -0.003(3) O3 0.048(4) 0.069(5) 0.034(4) -0.013(3) 0.030(3) -0.025(3) O8 0.048(4) 0.028(3) 0.032(4) -0.009(3) 0.021(3) -0.008(3) C22 0.039(5) 0.026(4) 0.022(5) 0.000(3) 0.015(4) -0.008(4) C9 0.039(5) 0.034(5) 0.027(5) -0.011(4) 0.022(4) -0.005(4) O2 0.101(5) 0.126(5) 0.073(5) 0.005(4) 0.044(4) -0.039(4) C18 0.032(4) 0.039(5) 0.017(4) 0.005(4) 0.014(4) -0.005(4) C7 0.035(5) 0.043(5) 0.016(4) 0.001(4) 0.013(4) -0.007(4) C5 0.042(5) 0.034(5) 0.031(5) -0.007(4) 0.020(4) -0.001(4) C15 0.064(6) 0.036(5) 0.022(5) 0.001(4) 0.022(5) 0.000(5) O6 0.057(4) 0.056(4) 0.024(3) 0.000(3) 0.015(3) 0.026(4) C11 0.026(4) 0.033(5) 0.023(4) 0.000(4) 0.010(4) -0.006(4) C8 0.032(5) 0.041(5) 0.012(4) -0.006(3) 0.012(4) -0.011(4) O1 0.137(9) 0.086(7) 0.254(15) -0.116(8) 0.146(11) -0.067(7) C12 0.049(6) 0.041(5) 0.027(5) -0.009(4) 0.020(5) 0.004(5) C4 0.102(9) 0.039(6) 0.034(6) 0.013(4) 0.038(6) 0.019(6) C13 0.050(6) 0.045(6) 0.035(6) -0.003(4) 0.016(5) 0.018(5) C14 0.068(7) 0.039(6) 0.046(7) 0.006(5) 0.023(6) 0.015(5) C1 0.065(7) 0.054(6) 0.046(7) 0.000(5) 0.030(6) 0.015(6) C2 0.102(9) 0.068(8) 0.052(8) 0.012(6) 0.053(7) 0.042(7) C3 0.131(12) 0.067(8) 0.057(8) 0.028(6) 0.052(8) 0.064(8) O1W 0.69(5) 0.37(3) 0.81(6) -0.36(4) 0.68(5) -0.30(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Lu1 O3 2.252(5) 7 ? Lu1 O8 2.327(6) 7_556 ? Lu1 O5 2.335(5) 1_556 ? Lu1 O7 2.337(5) . ? Lu1 O4 2.361(5) 2_554 ? Lu1 N3 2.423(6) . ? Lu1 N1 2.436(7) . ? Lu1 N2 2.442(6) . ? S2 O6 1.422(6) . ? S2 O4 1.452(5) . ? S2 O5 1.471(6) . ? S2 C19 1.770(7) . ? S1 O1 1.400(10) . ? S1 O2 1.424(9) . ? S1 O3 1.449(6) . ? S1 C17 1.786(8) . ? O4 Lu1 2.361(5) 2_554 ? O7 C22 1.267(9) . ? N2 C10 1.339(9) . ? N2 C6 1.347(10) . ? C19 C20 1.364(10) . ? C19 C18 1.386(10) . ? C6 C7 1.388(11) . ? C6 C5 1.496(11) . ? C16 C17 1.383(11) . ? C16 C21 1.379(11) . ? C16 C8 1.517(10) . ? N3 C15 1.350(10) . ? N3 C11 1.374(10) . ? N1 C5 1.347(10) . ? N1 C1 1.353(11) . ? O5 Lu1 2.335(5) 1_554 ? C17 C18 1.381(11) . ? C20 C21 1.400(11) . ? C10 C9 1.393(10) . ? C10 C11 1.500(11) . ? O3 Lu1 2.252(5) 7 ? O8 C22 1.248(9) . ? O8 Lu1 2.327(6) 7_556 ? C22 C22 1.540(16) 7_556 ? C9 C8 1.377(11) . ? C7 C8 1.356(11) . ? C5 C4 1.390(12) . ? C15 C14 1.352(12) . ? C11 C12 1.369(11) . ? C12 C13 1.366(12) . ? C4 C3 1.377(13) . ? C13 C14 1.380(13) . ? C1 C2 1.369(13) . ? C2 C3 1.353(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Lu1 O8 77.6(2) 7 7_556 ? O3 Lu1 O5 145.8(2) 7 1_556 ? O8 Lu1 O5 76.1(2) 7_556 1_556 ? O3 Lu1 O7 76.2(2) 7 . ? O8 Lu1 O7 69.86(19) 7_556 . ? O5 Lu1 O7 74.46(19) 1_556 . ? O3 Lu1 O4 142.13(19) 7 2_554 ? O8 Lu1 O4 127.00(19) 7_556 2_554 ? O5 Lu1 O4 72.02(18) 1_556 2_554 ? O7 Lu1 O4 135.57(18) . 2_554 ? O3 Lu1 N3 79.2(2) 7 . ? O8 Lu1 N3 78.9(2) 7_556 . ? O5 Lu1 N3 116.3(2) 1_556 . ? O7 Lu1 N3 143.5(2) . . ? O4 Lu1 N3 78.7(2) 2_554 . ? O3 Lu1 N1 91.0(2) 7 . ? O8 Lu1 N1 143.4(2) 7_556 . ? O5 Lu1 N1 97.2(2) 1_556 . ? O7 Lu1 N1 73.7(2) . . ? O4 Lu1 N1 82.4(2) 2_554 . ? N3 Lu1 N1 133.4(2) . . ? O3 Lu1 N2 74.8(2) 7 . ? O8 Lu1 N2 139.1(2) 7_556 . ? O5 Lu1 N2 138.7(2) 1_556 . ? O7 Lu1 N2 129.8(2) . . ? O4 Lu1 N2 68.31(19) 2_554 . ? N3 Lu1 N2 66.7(2) . . ? N1 Lu1 N2 66.8(2) . . ? O6 S2 O4 113.6(4) . . ? O6 S2 O5 114.0(4) . . ? O4 S2 O5 110.8(4) . . ? O6 S2 C19 106.0(4) . . ? O4 S2 C19 105.6(3) . . ? O5 S2 C19 106.1(3) . . ? O1 S1 O2 113.9(7) . . ? O1 S1 O3 114.2(6) . . ? O2 S1 O3 111.3(5) . . ? O1 S1 C17 107.7(5) . . ? O2 S1 C17 106.2(5) . . ? O3 S1 C17 102.4(4) . . ? S2 O4 Lu1 150.4(3) . 2_554 ? C22 O7 Lu1 118.5(5) . . ? C10 N2 C6 118.2(7) . . ? C10 N2 Lu1 121.2(5) . . ? C6 N2 Lu1 120.5(5) . . ? C20 C19 C18 119.4(7) . . ? C20 C19 S2 120.2(6) . . ? C18 C19 S2 120.3(6) . . ? N2 C6 C7 122.2(8) . . ? N2 C6 C5 115.5(7) . . ? C7 C6 C5 122.3(8) . . ? C17 C16 C21 117.5(8) . . ? C17 C16 C8 124.9(7) . . ? C21 C16 C8 117.3(7) . . ? C15 N3 C11 116.2(7) . . ? C15 N3 Lu1 122.8(5) . . ? C11 N3 Lu1 120.8(5) . . ? C5 N1 C1 117.8(8) . . ? C5 N1 Lu1 120.2(6) . . ? C1 N1 Lu1 121.9(6) . . ? S2 O5 Lu1 130.5(3) . 1_554 ? C18 C17 C16 122.0(8) . . ? C18 C17 S1 117.0(6) . . ? C16 C17 S1 120.7(6) . . ? C19 C20 C21 120.3(7) . . ? C16 C21 C20 121.0(8) . . ? N2 C10 C9 121.5(7) . . ? N2 C10 C11 115.9(7) . . ? C9 C10 C11 122.5(7) . . ? S1 O3 Lu1 148.6(4) . 7 ? C22 O8 Lu1 118.1(5) . 7_556 ? O8 C22 O7 126.5(8) . . ? O8 C22 C22 118.0(9) . 7_556 ? O7 C22 C22 115.5(9) . 7_556 ? C8 C9 C10 119.6(8) . . ? C17 C18 C19 119.6(7) . . ? C8 C7 C6 119.5(8) . . ? N1 C5 C4 121.9(8) . . ? N1 C5 C6 116.6(8) . . ? C4 C5 C6 121.5(8) . . ? N3 C15 C14 124.4(9) . . ? C12 C11 N3 121.2(8) . . ? C12 C11 C10 123.4(8) . . ? N3 C11 C10 115.4(7) . . ? C7 C8 C9 118.9(7) . . ? C7 C8 C16 121.3(8) . . ? C9 C8 C16 119.6(7) . . ? C13 C12 C11 120.8(8) . . ? C3 C4 C5 118.4(9) . . ? C12 C13 C14 118.4(9) . . ? C15 C14 C13 118.8(9) . . ? N1 C1 C2 122.6(10) . . ? C3 C2 C1 119.2(10) . . ? C2 C3 C4 120.2(10) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.644 _refine_diff_density_min -1.034 _refine_diff_density_rms 0.200 _database_code_depnum_ccdc_archive 'CCDC 946691' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_15 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N3 O13 S2 Yb' _chemical_formula_weight 774.59 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 8.9698(6) _cell_length_b 21.7582(15) _cell_length_c 13.4973(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.1640(10) _cell_angle_gamma 90.00 _cell_volume 2632.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6310 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.44 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.955 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 3.786 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3508 _exptl_absorpt_correction_T_max 0.4512 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15346 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5708 _reflns_number_gt 4869 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0400P)^2^+2.3688P] 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 5708 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Yb1 Yb 0.061896(18) 0.864206(8) 0.003237(11) 0.02373(7) Uani 1 1 d . . . S1 S 0.18291(11) 0.79039(5) -0.54967(7) 0.0291(2) Uani 1 1 d . . . S2 S -0.18994(12) 0.91254(6) -0.80874(7) 0.0342(2) Uani 1 1 d . . . N3 N -0.1655(4) 0.80884(16) -0.0579(2) 0.0291(8) Uani 1 1 d . . . N1 N 0.2925(4) 0.88954(18) -0.0804(2) 0.0314(8) Uani 1 1 d . . . N2 N 0.0484(4) 0.84728(16) -0.1772(2) 0.0265(7) Uani 1 1 d . . . C5 C 0.2938(5) 0.8916(2) -0.1807(3) 0.0308(9) Uani 1 1 d . . . C6 C 0.1517(5) 0.87337(19) -0.2338(3) 0.0271(9) Uani 1 1 d . . . C10 C -0.0777(4) 0.82652(19) -0.2208(3) 0.0276(9) Uani 1 1 d . . . C1 C 0.4179(5) 0.9060(3) -0.0298(4) 0.0449(12) Uani 1 1 d . . . H1A H 0.4173 0.9062 0.0391 0.054 Uiso 1 1 calc R . . C4 C 0.4195(5) 0.9083(2) -0.2292(4) 0.0437(12) Uani 1 1 d . . . H4A H 0.4181 0.9093 -0.2981 0.052 Uiso 1 1 calc R . . C7 C 0.1289(5) 0.8815(2) -0.3352(3) 0.0342(10) Uani 1 1 d . . . H7A H 0.2007 0.9009 -0.3721 0.041 Uiso 1 1 calc R . . C2 C 0.5472(5) 0.9226(3) -0.0744(4) 0.0505(13) Uani 1 1 d . . . H2A H 0.6321 0.9329 -0.0363 0.061 Uiso 1 1 calc R . . C3 C 0.5489(6) 0.9236(3) -0.1748(4) 0.0534(14) Uani 1 1 d . . . H3A H 0.6352 0.9344 -0.2067 0.064 Uiso 1 1 calc R . . C11 C -0.1859(4) 0.7967(2) -0.1561(3) 0.0292(9) Uani 1 1 d . . . O6 O -0.0946(4) 0.87269(14) -0.8692(2) 0.0350(7) Uani 1 1 d . . . O5 O -0.3435(4) 0.8938(2) -0.8176(3) 0.0628(11) Uani 1 1 d . . . O4 O -0.1649(5) 0.97643(17) -0.8249(3) 0.0567(10) Uani 1 1 d . . . C19 C -0.1291(5) 0.8966(2) -0.6847(3) 0.0290(9) Uani 1 1 d . . . O3 O 0.2992(3) 0.82237(15) -0.4922(2) 0.0385(7) Uani 1 1 d . . . O2 O 0.1217(3) 0.73902(14) -0.4926(2) 0.0339(7) Uani 1 1 d . . . O1 O 0.2251(4) 0.77169(16) -0.6472(2) 0.0418(8) Uani 1 1 d . . . O7 O 0.1371(3) 0.95928(14) 0.0668(2) 0.0329(7) Uani 1 1 d . . . C22 C 0.0637(4) 1.00578(19) 0.0394(3) 0.0257(8) Uani 1 1 d . . . C15 C -0.2622(5) 0.7828(2) 0.0035(3) 0.0405(11) Uani 1 1 d . . . H15A H -0.2506 0.7911 0.0709 0.049 Uiso 1 1 calc R . . C12 C -0.2983(5) 0.7585(2) -0.1922(4) 0.0434(12) Uani 1 1 d . . . H12A H -0.3096 0.7509 -0.2599 0.052 Uiso 1 1 calc R . . C8 C -0.0019(5) 0.8605(2) -0.3807(3) 0.0323(10) Uani 1 1 d . . . C9 C -0.1062(5) 0.8318(2) -0.3231(3) 0.0328(10) Uani 1 1 d . . . H9A H -0.1941 0.8163 -0.3522 0.039 Uiso 1 1 calc R . . C18 C -0.0135(5) 0.85593(19) -0.6652(3) 0.0287(9) Uani 1 1 d . . . H18A H 0.0339 0.8371 -0.7172 0.034 Uiso 1 1 calc R . . C14 C -0.3767(6) 0.7447(3) -0.0274(4) 0.0502(13) Uani 1 1 d . . . H14A H -0.4411 0.7282 0.0180 0.060 Uiso 1 1 calc R . . C13 C -0.3942(5) 0.7316(3) -0.1263(4) 0.0507(13) Uani 1 1 d . . . H13A H -0.4691 0.7051 -0.1491 0.061 Uiso 1 1 calc R . . C17 C 0.0320(4) 0.8432(2) -0.5675(3) 0.0273(8) Uani 1 1 d . . . C20 C -0.2007(5) 0.9253(2) -0.6086(3) 0.0432(12) Uani 1 1 d . . . H20A H -0.2773 0.9531 -0.6225 0.052 Uiso 1 1 calc R . . O8 O 0.0839(3) 1.05967(13) 0.0674(2) 0.0290(6) Uani 1 1 d . . . C16 C -0.0391(5) 0.8714(2) -0.4889(3) 0.0350(10) Uani 1 1 d . . . C21 C -0.1573(6) 0.9121(3) -0.5117(3) 0.0477(13) Uani 1 1 d . . . H21A H -0.2073 0.9305 -0.4604 0.057 Uiso 1 1 calc R . . O1W O 0.2265(4) 0.84689(15) 0.1355(2) 0.0387(7) Uani 1 1 d . . . H1WA H 0.1717 0.8334 0.1810 0.058 Uiso 1 1 d R . . H1WB H 0.2789 0.8168 0.1164 0.058 Uiso 1 1 d R . . O2W O 0.3831(4) 0.74439(18) 0.1792(3) 0.0586(10) Uani 1 1 d . . . H2WA H 0.4113 0.7079 0.1651 0.088 Uiso 1 1 d R . . H2WB H 0.3910 0.7483 0.2415 0.088 Uiso 1 1 d R . . O3W O 0.3829(5) 0.9223(3) 0.2647(4) 0.109(2) Uani 1 1 d . . . H3WA H 0.4645 0.9187 0.2336 0.163 Uiso 1 1 d R . . H3WB H 0.3151 0.9317 0.2239 0.163 Uiso 1 1 d R . . O4W O 0.1492(6) 1.0075(3) 0.2887(5) 0.123(2) Uani 1 1 d . . . H4WA H 0.1269 1.0456 0.2886 0.185 Uiso 1 1 d R . . H4WB H 0.0848 0.9888 0.3220 0.185 Uiso 1 1 d R . . O5W O 0.3933(11) 0.9529(5) 0.4794(7) 0.206(4) Uiso 1 1 d . . . H5WA H 0.4190 0.9153 0.4834 0.308 Uiso 1 1 d R . . H5WB H 0.3042 0.9551 0.5005 0.308 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Yb1 0.02673(10) 0.02865(11) 0.01565(10) -0.00044(6) -0.00137(6) -0.00085(7) S1 0.0298(5) 0.0345(6) 0.0231(5) 0.0016(4) 0.0017(4) 0.0041(4) S2 0.0363(6) 0.0487(7) 0.0175(5) 0.0040(4) 0.0009(4) 0.0072(5) N3 0.0298(17) 0.037(2) 0.0204(17) -0.0001(14) 0.0015(14) -0.0028(15) N1 0.0286(18) 0.042(2) 0.0232(18) -0.0004(15) -0.0017(14) -0.0011(16) N2 0.0279(17) 0.0339(19) 0.0177(16) -0.0012(13) 0.0009(13) 0.0001(14) C5 0.028(2) 0.037(2) 0.027(2) -0.0001(18) 0.0005(17) 0.0008(18) C6 0.028(2) 0.033(2) 0.020(2) 0.0011(16) 0.0017(16) 0.0010(17) C10 0.032(2) 0.032(2) 0.0182(19) -0.0027(16) -0.0004(16) 0.0017(17) C1 0.036(3) 0.063(3) 0.035(3) -0.004(2) -0.005(2) -0.011(2) C4 0.039(3) 0.059(3) 0.033(2) 0.003(2) 0.008(2) -0.005(2) C7 0.036(2) 0.045(3) 0.022(2) -0.0001(18) 0.0044(18) 0.001(2) C2 0.029(2) 0.068(4) 0.054(3) -0.004(3) -0.006(2) -0.009(2) C3 0.032(3) 0.070(4) 0.059(3) 0.003(3) 0.014(2) -0.006(2) C11 0.027(2) 0.037(2) 0.023(2) 0.0005(17) -0.0014(16) 0.0026(18) O6 0.0427(18) 0.0449(19) 0.0174(14) -0.0001(12) 0.0029(13) 0.0026(14) O5 0.0345(19) 0.120(4) 0.0332(19) -0.004(2) -0.0049(15) 0.003(2) O4 0.087(3) 0.043(2) 0.041(2) 0.0134(16) 0.0172(19) 0.0216(19) C19 0.032(2) 0.037(2) 0.0172(19) 0.0023(17) -0.0012(16) 0.0017(18) O3 0.0284(15) 0.0448(19) 0.0419(18) 0.0004(15) -0.0034(13) -0.0020(14) O2 0.0407(17) 0.0301(17) 0.0310(16) 0.0058(12) 0.0012(13) 0.0000(13) O1 0.0452(18) 0.052(2) 0.0292(16) -0.0024(14) 0.0083(14) 0.0111(16) O7 0.0340(16) 0.0351(17) 0.0288(16) -0.0016(13) -0.0080(13) 0.0026(13) C22 0.026(2) 0.033(2) 0.0182(19) -0.0003(16) -0.0012(15) -0.0039(17) C15 0.042(3) 0.051(3) 0.029(2) 0.001(2) 0.004(2) -0.013(2) C12 0.033(2) 0.063(3) 0.033(2) -0.010(2) -0.005(2) -0.010(2) C8 0.036(2) 0.044(3) 0.016(2) 0.0005(17) 0.0016(17) 0.0119(19) C9 0.034(2) 0.041(3) 0.023(2) -0.0044(18) -0.0045(17) 0.0020(19) C18 0.034(2) 0.034(2) 0.018(2) -0.0003(16) 0.0050(16) -0.0001(18) C14 0.038(3) 0.067(4) 0.046(3) 0.006(3) 0.007(2) -0.015(3) C13 0.035(3) 0.066(4) 0.050(3) -0.001(3) -0.003(2) -0.019(2) C17 0.030(2) 0.030(2) 0.022(2) 0.0015(16) 0.0027(16) 0.0016(17) C20 0.047(3) 0.057(3) 0.026(2) -0.003(2) 0.001(2) 0.022(2) O8 0.0328(15) 0.0282(16) 0.0253(15) -0.0038(12) -0.0065(12) -0.0007(12) C16 0.037(2) 0.049(3) 0.020(2) 0.0025(18) 0.0009(18) 0.005(2) C21 0.052(3) 0.071(4) 0.021(2) -0.006(2) 0.005(2) 0.026(3) O1W 0.0459(18) 0.0415(18) 0.0281(16) -0.0002(14) -0.0059(14) 0.0033(15) O2W 0.065(2) 0.064(3) 0.047(2) -0.0012(18) -0.0035(19) 0.008(2) O3W 0.061(3) 0.139(5) 0.125(5) -0.068(4) -0.004(3) -0.009(3) O4W 0.125(5) 0.134(6) 0.110(5) -0.020(4) 0.011(4) -0.005(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 Yb1 O6 2.269(3) 1_556 ? Yb1 O8 2.295(3) 3_575 ? Yb1 O1W 2.304(3) . ? Yb1 O2 2.309(3) 4_576 ? Yb1 O7 2.329(3) . ? Yb1 N1 2.456(3) . ? Yb1 N2 2.461(3) . ? Yb1 N3 2.483(3) . ? Yb1 C22 3.091(4) 3_575 ? Yb1 C22 3.119(4) . ? S1 O1 1.442(3) . ? S1 O3 1.453(3) . ? S1 O2 1.475(3) . ? S1 C17 1.785(4) . ? S2 O4 1.426(4) . ? S2 O5 1.437(4) . ? S2 O6 1.484(3) . ? S2 C19 1.775(4) . ? N3 C15 1.347(5) . ? N3 C11 1.357(5) . ? N1 C1 1.342(5) . ? N1 C5 1.355(5) . ? N2 C10 1.334(5) . ? N2 C6 1.349(5) . ? C5 C4 1.374(6) . ? C5 C6 1.492(6) . ? C6 C7 1.388(6) . ? C10 C9 1.400(5) . ? C10 C11 1.479(6) . ? C1 C2 1.374(7) . ? C4 C3 1.390(7) . ? C7 C8 1.381(6) . ? C2 C3 1.356(7) . ? C11 C12 1.382(6) . ? O6 Yb1 2.269(3) 1_554 ? C19 C20 1.380(6) . ? C19 C18 1.382(6) . ? O2 Yb1 2.309(3) 4_575 ? O7 C22 1.255(5) . ? C22 O8 1.243(5) . ? C22 C22 1.552(7) 3_575 ? C22 Yb1 3.091(4) 3_575 ? C15 C14 1.372(6) . ? C12 C13 1.390(7) . ? C8 C9 1.387(6) . ? C8 C16 1.505(6) . ? C18 C17 1.394(6) . ? C14 C13 1.369(7) . ? C17 C16 1.400(6) . ? C20 C21 1.381(6) . ? O8 Yb1 2.295(3) 3_575 ? C16 C21 1.406(6) . ? 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 O6 Yb1 O8 84.09(10) 1_556 3_575 ? O6 Yb1 O1W 79.77(11) 1_556 . ? O8 Yb1 O1W 141.09(10) 3_575 . ? O6 Yb1 O2 102.15(11) 1_556 4_576 ? O8 Yb1 O2 147.14(10) 3_575 4_576 ? O1W Yb1 O2 71.38(11) . 4_576 ? O6 Yb1 O7 80.05(11) 1_556 . ? O8 Yb1 O7 70.42(9) 3_575 . ? O1W Yb1 O7 72.04(11) . . ? O2 Yb1 O7 142.27(10) 4_576 . ? O6 Yb1 N1 152.40(12) 1_556 . ? O8 Yb1 N1 97.11(11) 3_575 . ? O1W Yb1 N1 82.34(12) . . ? O2 Yb1 N1 91.75(12) 4_576 . ? O7 Yb1 N1 74.51(11) . . ? O6 Yb1 N2 138.92(11) 1_556 . ? O8 Yb1 N2 72.00(11) 3_575 . ? O1W Yb1 N2 138.43(12) . . ? O2 Yb1 N2 83.18(11) 4_576 . ? O7 Yb1 N2 120.00(11) . . ? N1 Yb1 N2 65.78(11) . . ? O6 Yb1 N3 76.56(11) 1_556 . ? O8 Yb1 N3 76.35(11) 3_575 . ? O1W Yb1 N3 132.25(11) . . ? O2 Yb1 N3 73.94(11) 4_576 . ? O7 Yb1 N3 140.90(11) . . ? N1 Yb1 N3 130.66(11) . . ? N2 Yb1 N3 65.76(11) . . ? O6 Yb1 C22 80.50(10) 1_556 3_575 ? O8 Yb1 C22 20.66(9) 3_575 3_575 ? O1W Yb1 C22 120.81(11) . 3_575 ? O2 Yb1 C22 167.77(10) 4_576 3_575 ? O7 Yb1 C22 49.79(10) . 3_575 ? N1 Yb1 C22 90.95(11) . 3_575 ? N2 Yb1 C22 87.07(11) . 3_575 ? N3 Yb1 C22 95.34(11) . 3_575 ? O6 Yb1 C22 78.51(10) 1_556 . ? O8 Yb1 C22 49.60(9) 3_575 . ? O1W Yb1 C22 92.34(11) . . ? O2 Yb1 C22 163.13(10) 4_576 . ? O7 Yb1 C22 20.86(9) . . ? N1 Yb1 C22 81.41(11) . . ? N2 Yb1 C22 107.59(11) . . ? N3 Yb1 C22 122.05(11) . . ? C22 Yb1 C22 28.94(13) 3_575 . ? O1 S1 O3 114.49(19) . . ? O1 S1 O2 112.24(19) . . ? O3 S1 O2 110.97(18) . . ? O1 S1 C17 106.41(19) . . ? O3 S1 C17 106.83(19) . . ? O2 S1 C17 105.21(19) . . ? O4 S2 O5 114.8(3) . . ? O4 S2 O6 112.8(2) . . ? O5 S2 O6 111.0(2) . . ? O4 S2 C19 106.8(2) . . ? O5 S2 C19 106.4(2) . . ? O6 S2 C19 104.02(19) . . ? C15 N3 C11 116.9(4) . . ? C15 N3 Yb1 122.7(3) . . ? C11 N3 Yb1 119.8(3) . . ? C1 N1 C5 117.4(4) . . ? C1 N1 Yb1 122.0(3) . . ? C5 N1 Yb1 120.4(3) . . ? C10 N2 C6 118.8(3) . . ? C10 N2 Yb1 119.7(2) . . ? C6 N2 Yb1 119.2(3) . . ? N1 C5 C4 121.5(4) . . ? N1 C5 C6 115.6(4) . . ? C4 C5 C6 122.9(4) . . ? N2 C6 C7 122.2(4) . . ? N2 C6 C5 115.6(4) . . ? C7 C6 C5 122.1(4) . . ? N2 C10 C9 121.8(4) . . ? N2 C10 C11 116.9(3) . . ? C9 C10 C11 121.3(4) . . ? N1 C1 C2 123.5(4) . . ? C5 C4 C3 119.7(4) . . ? C8 C7 C6 119.2(4) . . ? C3 C2 C1 118.9(5) . . ? C2 C3 C4 118.9(5) . . ? N3 C11 C12 122.1(4) . . ? N3 C11 C10 115.1(4) . . ? C12 C11 C10 122.8(4) . . ? S2 O6 Yb1 148.28(19) . 1_554 ? C20 C19 C18 121.0(4) . . ? C20 C19 S2 118.6(3) . . ? C18 C19 S2 120.4(3) . . ? S1 O2 Yb1 144.59(18) . 4_575 ? C22 O7 Yb1 117.8(2) . . ? O8 C22 O7 127.0(4) . . ? O8 C22 C22 117.1(5) . 3_575 ? O7 C22 C22 115.8(4) . 3_575 ? O8 C22 Yb1 40.65(19) . 3_575 ? O7 C22 Yb1 167.4(3) . 3_575 ? C22 C22 Yb1 76.5(3) 3_575 3_575 ? O8 C22 Yb1 168.2(3) . . ? O7 C22 Yb1 41.37(18) . . ? C22 C22 Yb1 74.5(3) 3_575 . ? Yb1 C22 Yb1 151.06(13) 3_575 . ? N3 C15 C14 124.0(4) . . ? C11 C12 C13 119.2(4) . . ? C7 C8 C9 118.7(4) . . ? C7 C8 C16 122.2(4) . . ? C9 C8 C16 119.0(4) . . ? C8 C9 C10 119.2(4) . . ? C19 C18 C17 119.9(4) . . ? C13 C14 C15 118.6(5) . . ? C14 C13 C12 119.0(5) . . ? C18 C17 C16 120.3(4) . . ? C18 C17 S1 116.7(3) . . ? C16 C17 S1 123.0(3) . . ? C19 C20 C21 119.2(4) . . ? C22 O8 Yb1 118.7(2) . 3_575 ? C17 C16 C21 118.1(4) . . ? C17 C16 C8 125.1(4) . . ? C21 C16 C8 116.7(4) . . ? C20 C21 C16 121.4(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.145 _refine_diff_density_min -0.719 _refine_diff_density_rms 0.124 _database_code_depnum_ccdc_archive 'CCDC 946693' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_16 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 Lu N3 O13 S2' _chemical_formula_weight 776.52 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' Lu Lu -0.4720 5.8584 '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 8.983(2) _cell_length_b 21.722(5) _cell_length_c 13.532(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.122(3) _cell_angle_gamma 90.00 _cell_volume 2638.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1964 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 21.81 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.955 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1532 _exptl_absorpt_coefficient_mu 3.974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3819 _exptl_absorpt_correction_T_max 0.5871 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15188 _diffrn_reflns_av_R_equivalents 0.0725 _diffrn_reflns_av_sigmaI/netI 0.0941 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5703 _reflns_number_gt 3742 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0645P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5703 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0878 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _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 Lu1 Lu 0.06157(4) 0.864094(16) 0.00346(2) 0.03068(13) Uani 1 1 d . . . S1 S 0.1829(2) 0.79090(10) -0.54966(15) 0.0347(5) Uani 1 1 d . . . S2 S -0.1913(3) 0.91243(11) -0.80914(15) 0.0380(5) Uani 1 1 d . . . N3 N -0.1666(7) 0.8078(3) -0.0569(5) 0.0319(16) Uani 1 1 d . . . N1 N 0.2922(8) 0.8895(3) -0.0797(5) 0.0352(16) Uani 1 1 d . . . N2 N 0.0492(8) 0.8475(3) -0.1770(5) 0.0302(15) Uani 1 1 d . . . C5 C 0.2949(9) 0.8920(4) -0.1799(6) 0.0342(19) Uani 1 1 d . . . C6 C 0.1532(9) 0.8730(3) -0.2336(6) 0.0295(18) Uani 1 1 d . . . C10 C -0.0772(9) 0.8260(4) -0.2205(6) 0.0335(19) Uani 1 1 d . . . C1 C 0.4189(10) 0.9056(5) -0.0295(7) 0.047(2) Uani 1 1 d . . . H1A H 0.4191 0.9052 0.0393 0.056 Uiso 1 1 calc R . . C4 C 0.4213(10) 0.9078(4) -0.2293(7) 0.047(2) Uani 1 1 d . . . H4A H 0.4202 0.9076 -0.2980 0.057 Uiso 1 1 calc R . . C7 C 0.1290(10) 0.8818(4) -0.3347(6) 0.039(2) Uani 1 1 d . . . H7A H 0.2005 0.9015 -0.3715 0.047 Uiso 1 1 calc R . . C2 C 0.5474(11) 0.9227(4) -0.0741(8) 0.052(3) Uani 1 1 d . . . H2A H 0.6322 0.9332 -0.0363 0.063 Uiso 1 1 calc R . . C3 C 0.5484(11) 0.9239(5) -0.1762(8) 0.057(3) Uani 1 1 d . . . H3A H 0.6338 0.9354 -0.2084 0.068 Uiso 1 1 calc R . . C11 C -0.1852(9) 0.7967(4) -0.1550(6) 0.0321(19) Uani 1 1 d . . . O6 O -0.0944(7) 0.8729(2) -0.8695(4) 0.0370(14) Uani 1 1 d . . . O5 O -0.3458(7) 0.8930(4) -0.8168(5) 0.063(2) Uani 1 1 d . . . O4 O -0.1681(8) 0.9762(3) -0.8267(5) 0.061(2) Uani 1 1 d . . . C19 C -0.1300(9) 0.8976(4) -0.6853(6) 0.0313(18) Uani 1 1 d . . . O3 O 0.2995(6) 0.8231(3) -0.4923(4) 0.0425(15) Uani 1 1 d . . . O2 O 0.1220(7) 0.7399(3) -0.4927(4) 0.0412(15) Uani 1 1 d . . . O1 O 0.2245(7) 0.7721(3) -0.6476(4) 0.0462(16) Uani 1 1 d . . . O7 O 0.1362(6) 0.9591(3) 0.0672(4) 0.0373(14) Uani 1 1 d . . . C22 C 0.0633(8) 1.0060(4) 0.0400(6) 0.0331(19) Uani 1 1 d . . . C15 C -0.2592(10) 0.7824(4) 0.0061(7) 0.044(2) Uani 1 1 d . . . H15A H -0.2455 0.7902 0.0733 0.053 Uiso 1 1 calc R . . C12 C -0.2985(10) 0.7581(4) -0.1926(7) 0.044(2) Uani 1 1 d . . . H12A H -0.3101 0.7505 -0.2601 0.053 Uiso 1 1 calc R . . C8 C -0.0018(10) 0.8612(4) -0.3803(6) 0.037(2) Uani 1 1 d . . . C9 C -0.1061(9) 0.8330(4) -0.3220(6) 0.0335(19) Uani 1 1 d . . . H9A H -0.1954 0.8187 -0.3506 0.040 Uiso 1 1 calc R . . C18 C -0.0137(9) 0.8559(4) -0.6652(6) 0.0336(19) Uani 1 1 d . . . H18A H 0.0329 0.8365 -0.7169 0.040 Uiso 1 1 calc R . . C14 C -0.3764(10) 0.7441(5) -0.0265(7) 0.049(2) Uani 1 1 d . . . H14A H -0.4414 0.7276 0.0184 0.059 Uiso 1 1 calc R . . C13 C -0.3938(11) 0.7313(5) -0.1253(8) 0.056(3) Uani 1 1 d . . . H13A H -0.4691 0.7049 -0.1477 0.067 Uiso 1 1 calc R . . C17 C 0.0319(9) 0.8436(4) -0.5675(6) 0.0305(18) Uani 1 1 d . . . C20 C -0.2022(10) 0.9262(4) -0.6093(6) 0.047(2) Uani 1 1 d . . . H20A H -0.2804 0.9534 -0.6222 0.057 Uiso 1 1 calc R . . O8 O 0.0825(6) 1.0602(2) 0.0677(4) 0.0352(13) Uani 1 1 d . . . C16 C -0.0384(9) 0.8724(4) -0.4890(6) 0.040(2) Uani 1 1 d . . . C21 C -0.1529(11) 0.9128(4) -0.5119(6) 0.046(2) Uani 1 1 d . . . H21A H -0.2001 0.9321 -0.4603 0.056 Uiso 1 1 calc R . . O1W O 0.2254(7) 0.8469(3) 0.1349(4) 0.0438(15) Uani 1 1 d . . . H1WA H 0.1707 0.8334 0.1805 0.066 Uiso 1 1 d R . . H1WB H 0.2778 0.8168 0.1159 0.066 Uiso 1 1 d R . . O2W O 0.3808(8) 0.7442(3) 0.1772(5) 0.069(2) Uani 1 1 d . . . H2WA H 0.4090 0.7077 0.1631 0.104 Uiso 1 1 d R . . H2WB H 0.3888 0.7480 0.2395 0.104 Uiso 1 1 d R . . O3W O 0.3818(10) 0.9234(4) 0.2636(7) 0.112(4) Uani 1 1 d . . . H3WA H 0.4634 0.9198 0.2325 0.168 Uiso 1 1 d R . . H3WB H 0.3140 0.9328 0.2229 0.168 Uiso 1 1 d R . . O4W O 0.1516(14) 1.0062(5) 0.2879(10) 0.161(5) Uani 1 1 d . . . H4WA H 0.1293 1.0444 0.2878 0.241 Uiso 1 1 d R . . H4WB H 0.0872 0.9875 0.3212 0.241 Uiso 1 1 d R . . O5W O 0.3930(16) 0.9530(7) 0.4766(10) 0.180(6) Uiso 1 1 d . . . H5WA H 0.4187 0.9154 0.4805 0.270 Uiso 1 1 d R . . H5WB H 0.3039 0.9552 0.4976 0.270 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Lu1 0.0314(2) 0.0386(2) 0.02174(19) -0.00056(15) -0.00241(13) -0.00109(16) S1 0.0331(12) 0.0427(12) 0.0282(11) 0.0009(9) 0.0010(9) 0.0045(9) S2 0.0383(13) 0.0545(14) 0.0212(10) 0.0045(9) -0.0012(9) 0.0083(10) N3 0.027(4) 0.041(4) 0.027(4) -0.003(3) 0.005(3) 0.001(3) N1 0.031(4) 0.048(4) 0.027(4) -0.004(3) -0.001(3) -0.002(3) N2 0.033(4) 0.034(4) 0.023(3) -0.005(3) -0.003(3) 0.001(3) C5 0.022(4) 0.045(5) 0.036(5) 0.003(4) 0.001(3) 0.004(4) C6 0.027(4) 0.033(4) 0.028(4) 0.002(3) 0.001(3) 0.002(3) C10 0.035(5) 0.047(5) 0.019(4) -0.001(4) 0.001(3) 0.007(4) C1 0.031(5) 0.063(6) 0.046(6) -0.001(5) 0.001(4) -0.004(4) C4 0.041(6) 0.062(6) 0.038(5) 0.007(5) 0.004(4) -0.005(5) C7 0.035(5) 0.053(5) 0.030(5) -0.002(4) 0.007(4) 0.002(4) C2 0.035(6) 0.055(6) 0.067(7) -0.008(5) -0.003(5) -0.010(4) C3 0.038(6) 0.075(7) 0.058(7) -0.001(6) 0.003(5) -0.006(5) C11 0.033(5) 0.045(5) 0.018(4) -0.004(3) -0.007(3) 0.003(4) O6 0.044(4) 0.045(4) 0.022(3) -0.007(2) 0.004(3) 0.003(3) O5 0.028(4) 0.123(6) 0.037(4) -0.006(4) -0.002(3) 0.005(4) O4 0.093(6) 0.049(4) 0.040(4) 0.008(3) 0.012(4) 0.022(4) C19 0.030(5) 0.041(5) 0.023(4) 0.003(4) -0.002(3) 0.000(4) O3 0.031(3) 0.056(4) 0.040(4) -0.004(3) -0.009(3) 0.000(3) O2 0.040(4) 0.047(4) 0.037(4) 0.004(3) 0.000(3) -0.003(3) O1 0.038(4) 0.063(4) 0.038(4) -0.001(3) 0.003(3) 0.015(3) O7 0.031(3) 0.040(3) 0.040(4) 0.000(3) -0.008(3) 0.002(3) C22 0.030(5) 0.047(5) 0.022(4) 0.005(4) 0.003(3) 0.001(4) C15 0.040(6) 0.062(6) 0.031(5) 0.002(4) 0.002(4) -0.001(4) C12 0.032(5) 0.063(6) 0.038(5) -0.011(4) 0.000(4) -0.019(4) C8 0.043(5) 0.048(5) 0.020(4) -0.001(4) -0.003(4) 0.009(4) C9 0.033(5) 0.044(5) 0.023(4) -0.007(4) -0.007(3) 0.008(4) C18 0.032(5) 0.047(5) 0.022(4) 0.001(4) 0.002(3) -0.001(4) C14 0.035(6) 0.063(6) 0.050(6) 0.007(5) 0.001(4) -0.012(5) C13 0.045(6) 0.067(7) 0.054(7) -0.006(5) -0.005(5) -0.017(5) C17 0.030(5) 0.041(4) 0.020(4) 0.002(3) -0.007(3) 0.003(4) C20 0.042(6) 0.070(7) 0.030(5) -0.002(4) 0.001(4) 0.021(5) O8 0.037(4) 0.031(3) 0.036(3) -0.005(3) -0.010(3) -0.001(3) C16 0.034(5) 0.069(7) 0.016(4) -0.009(4) -0.003(3) 0.004(4) C21 0.069(7) 0.054(6) 0.016(4) -0.004(4) -0.002(4) 0.017(5) O1W 0.043(4) 0.050(4) 0.038(4) -0.006(3) -0.008(3) 0.004(3) O2W 0.067(6) 0.076(5) 0.064(5) -0.008(4) -0.013(4) 0.004(4) O3W 0.062(6) 0.145(9) 0.128(9) -0.063(7) 0.003(6) -0.017(5) O4W 0.199(13) 0.151(11) 0.133(11) -0.020(8) 0.011(9) -0.029(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 Lu1 O6 2.265(5) 1_556 ? Lu1 O8 2.284(6) 3_575 ? Lu1 O1W 2.297(6) . ? Lu1 O7 2.327(6) . ? Lu1 O2 2.324(6) 4_576 ? Lu1 N1 2.456(7) . ? Lu1 N2 2.467(6) . ? Lu1 N3 2.498(7) . ? S1 O1 1.449(6) . ? S1 O2 1.467(6) . ? S1 O3 1.460(6) . ? S1 C17 1.784(8) . ? S2 O4 1.422(7) . ? S2 O5 1.450(7) . ? S2 O6 1.489(5) . ? S2 C19 1.774(8) . ? N3 C15 1.332(10) . ? N3 C11 1.353(9) . ? N1 C5 1.359(10) . ? N1 C1 1.350(11) . ? N2 C6 1.349(10) . ? N2 C10 1.343(10) . ? C5 C4 1.382(11) . ? C5 C6 1.500(11) . ? C6 C7 1.391(11) . ? C10 C9 1.396(10) . ? C10 C11 1.483(11) . ? C1 C2 1.374(12) . ? C4 C3 1.371(13) . ? C7 C8 1.381(12) . ? C2 C3 1.383(14) . ? C11 C12 1.400(11) . ? O6 Lu1 2.265(5) 1_554 ? C19 C20 1.385(11) . ? C19 C18 1.401(11) . ? O2 Lu1 2.324(6) 4_575 ? O7 C22 1.258(9) . ? C22 O8 1.245(9) . ? C22 C22 1.562(16) 3_575 ? C15 C14 1.400(13) . ? C12 C13 1.400(12) . ? C8 C9 1.390(12) . ? C8 C16 1.514(11) . ? C18 C17 1.396(11) . ? C14 C13 1.368(13) . ? C17 C16 1.403(11) . ? C20 C21 1.405(12) . ? O8 Lu1 2.284(6) 3_575 ? C16 C21 1.378(12) . ? 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 O6 Lu1 O8 84.4(2) 1_556 3_575 ? O6 Lu1 O1W 79.8(2) 1_556 . ? O8 Lu1 O1W 141.3(2) 3_575 . ? O6 Lu1 O7 79.74(19) 1_556 . ? O8 Lu1 O7 70.62(19) 3_575 . ? O1W Lu1 O7 71.9(2) . . ? O6 Lu1 O2 102.42(19) 1_556 4_576 ? O8 Lu1 O2 146.9(2) 3_575 4_576 ? O1W Lu1 O2 71.4(2) . 4_576 ? O7 Lu1 O2 142.2(2) . 4_576 ? O6 Lu1 N1 152.2(2) 1_556 . ? O8 Lu1 N1 96.9(2) 3_575 . ? O1W Lu1 N1 82.2(2) . . ? O7 Lu1 N1 74.6(2) . . ? O2 Lu1 N1 91.6(2) 4_576 . ? O6 Lu1 N2 139.2(2) 1_556 . ? O8 Lu1 N2 71.6(2) 3_575 . ? O1W Lu1 N2 138.3(2) . . ? O7 Lu1 N2 119.9(2) . . ? O2 Lu1 N2 83.2(2) 4_576 . ? N1 Lu1 N2 65.6(2) . . ? O6 Lu1 N3 76.5(2) 1_556 . ? O8 Lu1 N3 76.7(2) 3_575 . ? O1W Lu1 N3 131.9(2) . . ? O7 Lu1 N3 141.0(2) . . ? O2 Lu1 N3 73.7(2) 4_576 . ? N1 Lu1 N3 131.0(2) . . ? N2 Lu1 N3 66.3(2) . . ? O1 S1 O2 112.4(4) . . ? O1 S1 O3 114.7(4) . . ? O2 S1 O3 110.9(4) . . ? O1 S1 C17 106.1(4) . . ? O2 S1 C17 105.0(4) . . ? O3 S1 C17 106.9(4) . . ? O4 S2 O5 114.6(5) . . ? O4 S2 O6 112.2(4) . . ? O5 S2 O6 111.7(4) . . ? O4 S2 C19 107.0(4) . . ? O5 S2 C19 106.1(4) . . ? O6 S2 C19 104.2(4) . . ? C15 N3 C11 119.7(7) . . ? C15 N3 Lu1 121.2(6) . . ? C11 N3 Lu1 118.5(5) . . ? C5 N1 C1 116.5(7) . . ? C5 N1 Lu1 120.8(5) . . ? C1 N1 Lu1 122.5(5) . . ? C6 N2 C10 119.0(7) . . ? C6 N2 Lu1 119.7(5) . . ? C10 N2 Lu1 119.4(5) . . ? N1 C5 C4 122.5(8) . . ? N1 C5 C6 115.2(7) . . ? C4 C5 C6 122.2(8) . . ? N2 C6 C7 122.0(8) . . ? N2 C6 C5 115.5(7) . . ? C7 C6 C5 122.5(7) . . ? N2 C10 C9 121.2(7) . . ? N2 C10 C11 116.6(7) . . ? C9 C10 C11 122.2(8) . . ? N1 C1 C2 123.8(9) . . ? C3 C4 C5 119.6(9) . . ? C8 C7 C6 119.6(8) . . ? C1 C2 C3 118.8(9) . . ? C4 C3 C2 118.8(9) . . ? N3 C11 C12 121.7(8) . . ? N3 C11 C10 116.8(7) . . ? C12 C11 C10 121.5(7) . . ? S2 O6 Lu1 148.8(3) . 1_554 ? C20 C19 C18 120.8(8) . . ? C20 C19 S2 118.9(7) . . ? C18 C19 S2 120.3(6) . . ? S1 O2 Lu1 144.4(4) . 4_575 ? C22 O7 Lu1 118.0(5) . . ? O8 C22 O7 127.7(8) . . ? O8 C22 C22 117.2(9) . 3_575 ? O7 C22 C22 115.1(9) . 3_575 ? N3 C15 C14 121.7(8) . . ? C11 C12 C13 117.8(8) . . ? C7 C8 C9 118.0(8) . . ? C7 C8 C16 122.1(8) . . ? C9 C8 C16 119.7(8) . . ? C10 C9 C8 120.1(8) . . ? C19 C18 C17 119.9(7) . . ? C13 C14 C15 119.0(9) . . ? C14 C13 C12 120.1(9) . . ? C18 C17 C16 120.5(8) . . ? C18 C17 S1 116.5(6) . . ? C16 C17 S1 123.0(6) . . ? C19 C20 C21 117.6(8) . . ? C22 O8 Lu1 118.9(5) . 3_575 ? C21 C16 C17 117.8(7) . . ? C21 C16 C8 117.1(7) . . ? C17 C16 C8 125.1(8) . . ? C16 C21 C20 123.4(8) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.672 _refine_diff_density_min -2.173 _refine_diff_density_rms 0.186 _database_code_depnum_ccdc_archive 'CCDC 946694' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_17 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C1.20 H1.40 N0.14 O0.72 S0.10 Yb0.05' _chemical_formula_weight 40.90 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.408(6) _cell_length_b 13.692(4) _cell_length_c 23.830(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.937(4) _cell_angle_gamma 90.00 _cell_volume 6332(3) _cell_formula_units_Z 166 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3376 _exptl_absorpt_coefficient_mu 3.161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5054 _exptl_absorpt_correction_T_max 0.6317 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17817 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0711 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6895 _reflns_number_gt 4739 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6895 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Yb1 Yb 1.258541(13) 0.61421(2) 0.856466(12) 0.03247(11) Uani 1 1 d . . . S1 S 1.18650(8) 0.84003(13) 0.91002(7) 0.0366(4) Uani 1 1 d . . . S2 S 0.93260(10) 0.72565(16) 0.97354(9) 0.0553(5) Uani 1 1 d . . . O8 O 1.1874(2) 0.6254(3) 0.77721(19) 0.0391(11) Uani 1 1 d . . . C1 C 1.1651(4) 1.3204(5) 0.6942(3) 0.051(2) Uani 1 1 d . . . H1A H 1.1913 1.3481 0.6660 0.061 Uiso 1 1 calc R . . O3 O 1.2091(2) 0.9378(3) 0.8969(2) 0.0497(13) Uani 1 1 d . . . O2W O 1.2306(2) 0.5959(3) 0.94844(19) 0.0461(12) Uani 1 1 d . . . H2WA H 1.2018 0.5615 0.9662 0.069 Uiso 1 1 d R . . H2WB H 1.2470 0.6382 0.9711 0.069 Uiso 1 1 d R . . O1W O 1.3601(3) 0.5961(5) 0.9028(3) 0.0810(19) Uani 1 1 d . . . H1WA H 1.3955 0.6321 0.9067 0.122 Uiso 1 1 d R . . H1WB H 1.3701 0.5402 0.9161 0.122 Uiso 1 1 d R . . O7 O 1.1371(2) 0.5925(3) 0.8565(2) 0.0437(12) Uani 1 1 d . . . N3 N 1.2551(3) 0.9370(4) 0.6430(2) 0.0434(15) Uani 1 1 d . . . C23 C 1.0643(3) 0.6179(4) 0.7760(3) 0.0323(14) Uani 1 1 d . . . N2 N 1.1754(2) 1.0283(4) 0.7159(2) 0.0309(11) Uani 1 1 d . . . C11 C 1.2240(3) 0.8796(4) 0.6811(3) 0.0332(14) Uani 1 1 d . . . O1 O 1.2182(2) 0.7676(3) 0.87300(19) 0.0446(12) Uani 1 1 d . . . C22 C 1.1334(3) 0.6115(4) 0.8058(3) 0.0343(15) Uani 1 1 d . . . O2 O 1.1935(2) 0.8131(4) 0.96804(19) 0.0514(13) Uani 1 1 d . . . N1 N 1.1672(3) 1.2220(4) 0.7009(2) 0.0395(13) Uani 1 1 d . . . C16 C 1.0680(3) 0.8823(4) 0.8471(3) 0.0365(15) Uani 1 1 d . . . C25 C 1.0582(3) 0.6188(4) 0.7185(3) 0.0393(16) Uani 1 1 d . . . H25A H 1.0979 0.6203 0.6971 0.047 Uiso 1 1 calc R . . C9 C 1.1502(3) 0.8818(5) 0.7661(3) 0.0364(15) Uani 1 1 d . . . H9A H 1.1576 0.8152 0.7710 0.044 Uiso 1 1 calc R . . C21 C 0.9957(4) 0.8806(5) 0.8405(3) 0.0478(19) Uani 1 1 d . . . H21A H 0.9752 0.9113 0.8096 0.057 Uiso 1 1 calc R . . C24 C 1.0043(3) 0.6178(5) 0.8080(3) 0.0420(16) Uani 1 1 d . . . H24A H 1.0073 0.6169 0.8470 0.050 Uiso 1 1 calc R . . C6 C 1.1347(3) 1.0767(5) 0.7519(3) 0.0359(15) Uani 1 1 d . . . C10 C 1.1814(3) 0.9310(4) 0.7225(3) 0.0303(13) Uani 1 1 d . . . C5 C 1.1294(3) 1.1849(5) 0.7431(3) 0.0362(15) Uani 1 1 d . . . C18 C 1.0552(3) 0.7887(5) 0.9322(3) 0.0396(16) Uani 1 1 d . . . H18A H 1.0747 0.7587 0.9636 0.048 Uiso 1 1 calc R . . C17 C 1.0962(3) 0.8356(5) 0.8939(3) 0.0332(14) Uani 1 1 d . . . O6 O 0.9277(4) 0.7936(6) 1.0200(3) 0.110(3) Uani 1 1 d . . . C19 C 0.9849(3) 0.7869(5) 0.9233(3) 0.0417(16) Uani 1 1 d . . . C12 C 1.2290(3) 0.7796(5) 0.6798(3) 0.0402(16) Uani 1 1 d . . . H12A H 1.2073 0.7419 0.7068 0.048 Uiso 1 1 calc R . . C8 C 1.1080(3) 0.9321(5) 0.8022(3) 0.0357(15) Uani 1 1 d . . . C2 C 1.1265(4) 1.3812(5) 0.7270(4) 0.063(2) Uani 1 1 d . . . H2A H 1.1263 1.4481 0.7202 0.076 Uiso 1 1 calc R . . O5 O 0.8680(3) 0.7096(6) 0.9473(3) 0.103(2) Uani 1 1 d . . . O4 O 0.9691(4) 0.6418(5) 0.9898(4) 0.128(3) Uani 1 1 d . . . C20 C 0.9546(3) 0.8340(6) 0.8791(3) 0.0495(19) Uani 1 1 d . . . H20A H 0.9069 0.8349 0.8749 0.059 Uiso 1 1 calc R . . C4 C 1.0901(4) 1.2431(5) 0.7769(3) 0.053(2) Uani 1 1 d . . . H4A H 1.0644 1.2147 0.8052 0.063 Uiso 1 1 calc R . . C7 C 1.1002(3) 1.0310(5) 0.7942(3) 0.0421(17) Uani 1 1 d . . . H7A H 1.0717 1.0668 0.8175 0.051 Uiso 1 1 calc R . . C15 C 1.2931(5) 0.8920(5) 0.6032(4) 0.074(3) Uani 1 1 d . . . H15A H 1.3166 0.9302 0.5776 0.089 Uiso 1 1 calc R . . C14 C 1.2982(4) 0.7930(6) 0.5994(4) 0.070(3) Uani 1 1 d . . . H14A H 1.3232 0.7649 0.5707 0.083 Uiso 1 1 calc R . . C13 C 1.2667(4) 0.7352(5) 0.6377(3) 0.0506(19) Uani 1 1 d . . . H13A H 1.2702 0.6676 0.6358 0.061 Uiso 1 1 calc R . . C3 C 1.0882(4) 1.3435(5) 0.7694(3) 0.055(2) Uani 1 1 d . . . H3A H 1.0621 1.3835 0.7924 0.066 Uiso 1 1 calc R . . O3W O 1.4813(3) 0.6909(7) 0.8853(3) 0.118(3) Uani 1 1 d . . . O7W O 1.1005(4) 0.5515(6) 0.9815(3) 0.114(3) Uani 1 1 d . . . O6W O 0.8487(4) 0.5170(5) 0.8943(3) 0.113(3) Uani 1 1 d . . . O5W O 1.3691(5) 0.4782(6) 0.9956(3) 0.159(4) Uani 1 1 d . . . O4W O 1.4753(6) 0.8917(7) 0.8914(4) 0.172(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 Yb1 0.03011(17) 0.03595(17) 0.03144(17) -0.00257(12) 0.00327(11) 0.00192(12) S1 0.0302(8) 0.0398(9) 0.0397(10) -0.0077(8) -0.0001(7) 0.0032(7) S2 0.0438(11) 0.0626(13) 0.0598(14) 0.0190(10) 0.0125(10) -0.0063(10) O8 0.031(2) 0.049(3) 0.037(3) 0.003(2) 0.004(2) -0.006(2) C1 0.047(4) 0.035(4) 0.070(6) 0.010(4) 0.021(4) 0.010(3) O3 0.045(3) 0.033(3) 0.071(4) -0.007(2) 0.001(2) -0.008(2) O2W 0.055(3) 0.048(3) 0.036(3) -0.007(2) 0.004(2) -0.006(2) O1W 0.044(3) 0.134(6) 0.064(4) 0.007(4) -0.011(3) -0.010(3) O7 0.035(3) 0.054(3) 0.042(3) 0.006(2) 0.002(2) -0.001(2) N3 0.052(4) 0.035(3) 0.043(4) -0.001(3) 0.019(3) 0.002(3) C23 0.027(3) 0.030(3) 0.039(4) 0.002(3) -0.004(3) -0.001(3) N2 0.028(3) 0.038(3) 0.027(3) 0.002(2) 0.004(2) 0.002(2) C11 0.031(3) 0.036(4) 0.033(4) -0.001(3) 0.002(3) -0.001(3) O1 0.042(3) 0.045(3) 0.047(3) -0.012(2) 0.010(2) 0.004(2) C22 0.035(4) 0.025(3) 0.043(4) -0.002(3) 0.003(3) -0.003(3) O2 0.050(3) 0.069(3) 0.035(3) -0.004(2) -0.007(2) 0.002(3) N1 0.035(3) 0.038(3) 0.046(4) 0.004(3) 0.005(3) 0.001(3) C16 0.036(4) 0.041(4) 0.033(4) 0.003(3) 0.007(3) 0.004(3) C25 0.030(3) 0.047(4) 0.041(4) 0.007(3) 0.006(3) 0.000(3) C9 0.036(4) 0.038(4) 0.036(4) 0.002(3) 0.004(3) 0.000(3) C21 0.035(4) 0.066(5) 0.043(4) 0.022(4) -0.002(3) 0.001(3) C24 0.043(4) 0.049(4) 0.034(4) -0.005(3) -0.006(3) 0.002(3) C6 0.027(3) 0.044(4) 0.036(4) 0.002(3) 0.004(3) 0.001(3) C10 0.028(3) 0.035(3) 0.029(3) -0.002(3) 0.004(3) 0.003(3) C5 0.032(3) 0.039(4) 0.038(4) -0.001(3) 0.000(3) 0.006(3) C18 0.047(4) 0.038(4) 0.034(4) 0.005(3) 0.000(3) 0.000(3) C17 0.033(3) 0.035(4) 0.032(4) -0.001(3) 0.003(3) 0.001(3) O6 0.121(6) 0.156(7) 0.055(4) -0.015(4) 0.039(4) -0.055(5) C19 0.034(4) 0.048(4) 0.044(4) 0.004(3) 0.007(3) -0.005(3) C12 0.039(4) 0.040(4) 0.042(4) 0.000(3) 0.008(3) -0.005(3) C8 0.031(3) 0.046(4) 0.031(4) 0.006(3) 0.003(3) -0.008(3) C2 0.067(6) 0.044(5) 0.080(7) 0.009(4) 0.007(5) 0.014(4) O5 0.063(4) 0.146(7) 0.101(6) 0.045(5) -0.004(4) -0.042(4) O4 0.092(5) 0.107(6) 0.188(9) 0.089(6) 0.064(6) 0.019(4) C20 0.029(4) 0.065(5) 0.054(5) 0.010(4) 0.005(3) 0.001(4) C4 0.054(5) 0.043(4) 0.062(5) 0.008(4) 0.018(4) 0.004(4) C7 0.042(4) 0.046(4) 0.039(4) -0.004(3) 0.013(3) 0.002(3) C15 0.079(6) 0.036(4) 0.109(8) 0.008(4) 0.061(6) 0.011(4) C14 0.082(6) 0.060(5) 0.068(6) -0.002(4) 0.044(5) 0.014(5) C13 0.057(5) 0.035(4) 0.059(5) -0.004(3) 0.013(4) 0.005(4) C3 0.064(5) 0.042(4) 0.059(5) -0.003(4) 0.015(4) 0.010(4) O3W 0.069(4) 0.202(9) 0.083(6) 0.018(5) 0.011(4) -0.021(5) O7W 0.086(5) 0.126(6) 0.130(7) 0.052(5) 0.043(5) 0.023(5) O6W 0.093(5) 0.102(5) 0.144(8) -0.019(5) 0.013(5) -0.017(4) O5W 0.266(12) 0.122(7) 0.090(6) 0.001(5) 0.006(7) 0.099(7) O4W 0.220(12) 0.204(11) 0.091(8) -0.011(6) -0.032(8) 0.051(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 Yb1 O1W 2.257(6) . ? Yb1 O1 2.278(4) . ? Yb1 O2W 2.280(5) . ? Yb1 O8 2.327(5) . ? Yb1 O7 2.375(4) . ? Yb1 N3 2.440(6) 4_746 ? Yb1 N2 2.465(5) 4_746 ? Yb1 N1 2.487(5) 4_746 ? Yb1 C22 2.695(7) . ? S1 O2 1.436(5) . ? S1 O3 1.445(5) . ? S1 O1 1.469(4) . ? S1 C17 1.788(6) . ? S2 O5 1.410(6) . ? S2 O4 1.400(7) . ? S2 O6 1.450(7) . ? S2 C19 1.791(7) . ? O8 C22 1.274(7) . ? C1 N1 1.358(8) . ? C1 C2 1.373(10) . ? O7 C22 1.238(8) . ? N3 C11 1.353(8) . ? N3 C15 1.357(9) . ? N3 Yb1 2.440(6) 4_756 ? C23 C24 1.403(9) . ? C23 C25 1.374(9) . ? C23 C22 1.508(9) . ? N2 C10 1.345(7) . ? N2 C6 1.349(7) . ? N2 Yb1 2.465(5) 4_756 ? C11 C12 1.373(8) . ? C11 C10 1.476(8) . ? N1 C5 1.354(8) . ? N1 Yb1 2.487(5) 4_756 ? C16 C17 1.392(9) . ? C16 C21 1.409(9) . ? C16 C8 1.495(8) . ? C25 C24 1.359(9) 2_756 ? C9 C8 1.383(8) . ? C9 C10 1.386(8) . ? C21 C20 1.383(9) . ? C24 C25 1.359(9) 2_756 ? C6 C7 1.372(9) . ? C6 C5 1.500(9) . ? C5 C4 1.373(9) . ? C18 C17 1.379(8) . ? C18 C19 1.377(9) . ? C19 C20 1.360(9) . ? C12 C13 1.391(9) . ? C8 C7 1.375(9) . ? C2 C3 1.366(11) . ? C4 C3 1.387(10) . ? C15 C14 1.362(10) . ? C14 C13 1.359(10) . ? 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 O1W Yb1 O1 108.5(2) . . ? O1W Yb1 O2W 74.8(2) . . ? O1 Yb1 O2W 81.21(16) . . ? O1W Yb1 O8 155.0(2) . . ? O1 Yb1 O8 83.03(16) . . ? O2W Yb1 O8 129.81(16) . . ? O1W Yb1 O7 147.6(2) . . ? O1 Yb1 O7 76.82(15) . . ? O2W Yb1 O7 74.58(17) . . ? O8 Yb1 O7 55.46(16) . . ? O1W Yb1 N3 89.0(2) . 4_746 ? O1 Yb1 N3 151.39(16) . 4_746 ? O2W Yb1 N3 81.83(17) . 4_746 ? O8 Yb1 N3 90.40(17) . 4_746 ? O7 Yb1 N3 76.55(17) . 4_746 ? O1W Yb1 N2 80.2(2) . 4_746 ? O1 Yb1 N2 138.19(16) . 4_746 ? O2W Yb1 N2 138.99(16) . 4_746 ? O8 Yb1 N2 76.84(16) . 4_746 ? O7 Yb1 N2 117.92(16) . 4_746 ? N3 Yb1 N2 65.62(16) 4_746 4_746 ? O1W Yb1 N1 79.9(2) . 4_746 ? O1 Yb1 N1 75.61(16) . 4_746 ? O2W Yb1 N1 137.92(17) . 4_746 ? O8 Yb1 N1 81.75(17) . 4_746 ? O7 Yb1 N1 131.18(17) . 4_746 ? N3 Yb1 N1 131.07(17) 4_746 4_746 ? N2 Yb1 N1 65.56(17) 4_746 4_746 ? O1W Yb1 C22 172.3(2) . . ? O1 Yb1 C22 77.34(17) . . ? O2W Yb1 C22 101.68(19) . . ? O8 Yb1 C22 28.18(17) . . ? O7 Yb1 C22 27.33(17) . . ? N3 Yb1 C22 83.77(19) 4_746 . ? N2 Yb1 C22 98.94(18) 4_746 . ? N1 Yb1 C22 106.75(19) 4_746 . ? O2 S1 O3 114.9(3) . . ? O2 S1 O1 111.8(3) . . ? O3 S1 O1 111.4(3) . . ? O2 S1 C17 106.0(3) . . ? O3 S1 C17 106.6(3) . . ? O1 S1 C17 105.5(3) . . ? O5 S2 O4 115.9(5) . . ? O5 S2 O6 111.7(5) . . ? O4 S2 O6 110.7(6) . . ? O5 S2 C19 106.6(4) . . ? O4 S2 C19 106.2(4) . . ? O6 S2 C19 104.8(4) . . ? C22 O8 Yb1 92.2(4) . . ? N1 C1 C2 123.4(7) . . ? C22 O7 Yb1 90.9(4) . . ? C11 N3 C15 117.3(6) . . ? C11 N3 Yb1 121.6(4) . 4_756 ? C15 N3 Yb1 121.1(5) . 4_756 ? C24 C23 C25 118.9(6) . . ? C24 C23 C22 118.9(6) . . ? C25 C23 C22 122.1(6) . . ? C10 N2 C6 117.6(5) . . ? C10 N2 Yb1 120.6(4) . 4_756 ? C6 N2 Yb1 121.8(4) . 4_756 ? N3 C11 C12 122.1(6) . . ? N3 C11 C10 115.7(5) . . ? C12 C11 C10 122.1(6) . . ? S1 O1 Yb1 151.0(3) . . ? O7 C22 O8 121.2(6) . . ? O7 C22 C23 120.7(6) . . ? O8 C22 C23 118.2(6) . . ? O7 C22 Yb1 61.8(3) . . ? O8 C22 Yb1 59.6(3) . . ? C23 C22 Yb1 175.6(4) . . ? C5 N1 C1 116.3(6) . . ? C5 N1 Yb1 120.8(4) . 4_756 ? C1 N1 Yb1 122.8(4) . 4_756 ? C17 C16 C21 117.4(6) . . ? C17 C16 C8 125.5(6) . . ? C21 C16 C8 117.1(6) . . ? C24 C25 C23 121.7(6) 2_756 . ? C8 C9 C10 119.6(6) . . ? C20 C21 C16 121.1(6) . . ? C25 C24 C23 119.3(7) 2_756 . ? N2 C6 C7 122.8(6) . . ? N2 C6 C5 115.9(5) . . ? C7 C6 C5 121.3(6) . . ? N2 C10 C9 122.1(5) . . ? N2 C10 C11 116.3(5) . . ? C9 C10 C11 121.6(6) . . ? N1 C5 C4 122.1(6) . . ? N1 C5 C6 115.9(5) . . ? C4 C5 C6 122.0(6) . . ? C17 C18 C19 119.2(6) . . ? C18 C17 C16 121.3(6) . . ? C18 C17 S1 116.6(5) . . ? C16 C17 S1 121.9(5) . . ? C20 C19 C18 121.7(6) . . ? C20 C19 S2 119.8(5) . . ? C18 C19 S2 118.5(5) . . ? C13 C12 C11 119.4(6) . . ? C7 C8 C9 118.0(6) . . ? C7 C8 C16 119.4(6) . . ? C9 C8 C16 122.5(6) . . ? C3 C2 C1 120.1(7) . . ? C19 C20 C21 119.2(6) . . ? C3 C4 C5 120.9(7) . . ? C8 C7 C6 119.8(6) . . ? C14 C15 N3 122.7(7) . . ? C15 C14 C13 120.0(7) . . ? C12 C13 C14 118.5(7) . . ? C2 C3 C4 117.1(7) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.233 _refine_diff_density_min -0.853 _refine_diff_density_rms 0.148 _database_code_depnum_ccdc_archive 'CCDC 946695' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_18 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H29 Lu N3 O15 S2' _chemical_formula_weight 850.60 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' Lu Lu -0.4720 5.8584 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.4274(14) _cell_length_b 13.6955(10) _cell_length_c 23.8550(17) _cell_angle_alpha 90.00 _cell_angle_beta 91.0040(10) _cell_angle_gamma 90.00 _cell_volume 6346.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4281 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 24.25 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3384 _exptl_absorpt_coefficient_mu 3.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5289 _exptl_absorpt_correction_T_max 0.6024 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18384 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6907 _reflns_number_gt 5218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0516P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6907 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.005 _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 Lu1 Lu 1.258178(10) 0.615254(16) 0.855961(8) 0.02870(8) Uani 1 1 d . . . S1 S 1.18726(6) 0.84047(10) 0.90989(5) 0.0332(3) Uani 1 1 d . . . S2 S 0.93339(7) 0.72748(12) 0.97395(6) 0.0493(4) Uani 1 1 d . . . O8 O 1.18746(17) 0.6264(2) 0.77677(14) 0.0364(8) Uani 1 1 d . . . C1 C 1.1651(3) 1.3221(4) 0.6937(2) 0.0468(14) Uani 1 1 d . . . H1A H 1.1910 1.3496 0.6653 0.056 Uiso 1 1 calc R . . O3 O 1.21023(19) 0.9384(3) 0.89714(17) 0.0483(10) Uani 1 1 d . . . O2W O 1.23085(19) 0.5973(3) 0.94769(14) 0.0411(9) Uani 1 1 d . . . H2WA H 1.2021 0.5629 0.9654 0.062 Uiso 1 1 d R . . H2WB H 1.2473 0.6396 0.9703 0.062 Uiso 1 1 d R . . O1W O 1.3593(2) 0.5996(3) 0.90189(17) 0.0609(12) Uani 1 1 d . . . H1WA H 1.3946 0.6357 0.9058 0.091 Uiso 1 1 d R . . H1WB H 1.3693 0.5437 0.9152 0.091 Uiso 1 1 d R . . O7 O 1.13758(18) 0.5934(3) 0.85613(15) 0.0422(9) Uani 1 1 d . . . N3 N 1.2550(2) 0.9385(3) 0.64280(16) 0.0397(11) Uani 1 1 d . . . C23 C 1.0643(2) 0.6197(3) 0.7764(2) 0.0299(11) Uani 1 1 d . . . N2 N 1.17550(19) 1.0294(3) 0.71619(15) 0.0285(9) Uani 1 1 d . . . C11 C 1.2240(3) 0.8817(4) 0.6805(2) 0.0328(11) Uani 1 1 d . . . O1 O 1.21897(16) 0.7682(3) 0.87276(14) 0.0388(9) Uani 1 1 d . . . C22 C 1.1332(3) 0.6123(3) 0.8049(2) 0.0320(11) Uani 1 1 d . . . O2 O 1.19431(17) 0.8134(3) 0.96826(14) 0.0476(10) Uani 1 1 d . . . N1 N 1.1672(2) 1.2237(3) 0.70093(17) 0.0348(10) Uani 1 1 d . . . C16 C 1.0687(3) 0.8831(4) 0.8471(2) 0.0334(11) Uani 1 1 d . . . C25 C 1.0588(3) 0.6206(4) 0.7180(2) 0.0349(12) Uani 1 1 d . . . H25A H 1.0984 0.6223 0.6967 0.042 Uiso 1 1 calc R . . C9 C 1.1507(3) 0.8824(4) 0.7662(2) 0.0323(11) Uani 1 1 d . . . H9A H 1.1579 0.8158 0.7710 0.039 Uiso 1 1 calc R . . C21 C 0.9966(3) 0.8819(4) 0.8409(2) 0.0448(14) Uani 1 1 d . . . H21A H 0.9761 0.9129 0.8102 0.054 Uiso 1 1 calc R . . C24 C 1.0049(3) 0.6191(4) 0.8082(2) 0.0361(12) Uani 1 1 d . . . H24A H 1.0082 0.6176 0.8471 0.043 Uiso 1 1 calc R . . C6 C 1.1353(2) 1.0791(4) 0.7517(2) 0.0345(11) Uani 1 1 d . . . C10 C 1.1821(2) 0.9326(4) 0.72250(19) 0.0290(10) Uani 1 1 d . . . C5 C 1.1300(2) 1.1861(4) 0.7431(2) 0.0323(11) Uani 1 1 d . . . C18 C 1.0562(2) 0.7897(4) 0.9321(2) 0.0353(12) Uani 1 1 d . . . H18A H 1.0759 0.7593 0.9633 0.042 Uiso 1 1 calc R . . C17 C 1.0975(2) 0.8365(4) 0.89412(19) 0.0307(11) Uani 1 1 d . . . O6 O 0.9280(3) 0.7967(4) 1.02033(18) 0.0824(16) Uani 1 1 d . . . C19 C 0.9855(2) 0.7876(4) 0.9240(2) 0.0353(12) Uani 1 1 d . . . C12 C 1.2293(3) 0.7808(4) 0.6788(2) 0.0381(12) Uani 1 1 d . . . H12A H 1.2075 0.7434 0.7057 0.046 Uiso 1 1 calc R . . C8 C 1.1087(2) 0.9335(4) 0.80247(19) 0.0319(11) Uani 1 1 d . . . C2 C 1.1265(3) 1.3828(4) 0.7267(3) 0.0563(17) Uani 1 1 d . . . H2A H 1.1262 1.4498 0.7202 0.068 Uiso 1 1 calc R . . O5 O 0.8692(2) 0.7097(4) 0.9476(2) 0.0854(17) Uani 1 1 d . . . O4 O 0.9707(3) 0.6434(4) 0.9910(3) 0.102(2) Uani 1 1 d . . . C20 C 0.9554(3) 0.8352(5) 0.8797(2) 0.0466(14) Uani 1 1 d . . . H20A H 0.9077 0.8364 0.8754 0.056 Uiso 1 1 calc R . . C4 C 1.0904(3) 1.2461(4) 0.7769(2) 0.0492(15) Uani 1 1 d . . . H4A H 1.0648 1.2185 0.8054 0.059 Uiso 1 1 calc R . . C7 C 1.1005(3) 1.0321(4) 0.7944(2) 0.0370(12) Uani 1 1 d . . . H7A H 1.0716 1.0676 0.8175 0.044 Uiso 1 1 calc R . . C15 C 1.2938(4) 0.8930(5) 0.6031(3) 0.066(2) Uani 1 1 d . . . H15A H 1.3175 0.9314 0.5777 0.080 Uiso 1 1 calc R . . C14 C 1.2994(3) 0.7942(5) 0.5992(3) 0.0632(19) Uani 1 1 d . . . H14A H 1.3251 0.7663 0.5708 0.076 Uiso 1 1 calc R . . C13 C 1.2666(3) 0.7354(5) 0.6376(2) 0.0497(15) Uani 1 1 d . . . H13A H 1.2697 0.6677 0.6358 0.060 Uiso 1 1 calc R . . C3 C 1.0885(3) 1.3441(5) 0.7688(3) 0.0540(16) Uani 1 1 d . . . H3A H 1.0620 1.3840 0.7915 0.065 Uiso 1 1 calc R . . O3W O 1.4810(2) 0.6925(5) 0.8849(2) 0.100(2) Uani 1 1 d . . . O7W O 1.1023(3) 0.5518(5) 0.9822(2) 0.105(2) Uani 1 1 d . . . O6W O 0.8499(3) 0.5182(4) 0.8954(2) 0.1001(18) Uani 1 1 d . . . O5W O 1.3692(4) 0.4803(5) 0.9938(2) 0.147(3) Uani 1 1 d . . . O4W O 1.4772(5) 0.8948(6) 0.8899(3) 0.144(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 Lu1 0.02627(13) 0.03303(14) 0.02687(12) -0.00254(9) 0.00230(8) 0.00152(9) S1 0.0287(6) 0.0375(8) 0.0334(6) -0.0071(6) 0.0001(5) 0.0022(5) S2 0.0408(8) 0.0529(10) 0.0546(9) 0.0173(8) 0.0128(7) -0.0046(7) O8 0.0287(19) 0.048(2) 0.0321(19) 0.0019(16) -0.0014(15) -0.0041(15) C1 0.048(3) 0.037(3) 0.056(4) 0.013(3) 0.020(3) 0.011(3) O3 0.041(2) 0.037(2) 0.067(3) -0.006(2) -0.0017(19) -0.0029(18) O2W 0.047(2) 0.046(2) 0.0299(19) -0.0042(16) 0.0038(16) -0.0067(17) O1W 0.042(2) 0.089(4) 0.051(3) 0.005(2) -0.006(2) 0.002(2) O7 0.0299(19) 0.064(3) 0.033(2) 0.0045(18) 0.0002(15) -0.0016(17) N3 0.049(3) 0.037(3) 0.034(2) 0.001(2) 0.015(2) 0.004(2) C23 0.030(3) 0.024(3) 0.036(3) -0.002(2) -0.004(2) -0.002(2) N2 0.025(2) 0.031(2) 0.030(2) 0.0002(18) 0.0043(16) 0.0017(17) C11 0.027(3) 0.039(3) 0.033(3) 0.003(2) 0.000(2) -0.002(2) O1 0.035(2) 0.042(2) 0.039(2) -0.0084(17) 0.0071(15) 0.0055(16) C22 0.029(3) 0.025(3) 0.042(3) -0.002(2) 0.000(2) -0.003(2) O2 0.039(2) 0.069(3) 0.034(2) -0.0048(19) -0.0068(16) 0.0022(19) N1 0.031(2) 0.029(2) 0.045(2) 0.006(2) 0.0077(19) 0.0021(18) C16 0.034(3) 0.037(3) 0.030(3) 0.000(2) 0.008(2) 0.000(2) C25 0.030(3) 0.038(3) 0.038(3) 0.007(2) 0.008(2) 0.002(2) C9 0.033(3) 0.034(3) 0.029(3) 0.006(2) 0.002(2) 0.000(2) C21 0.031(3) 0.062(4) 0.041(3) 0.015(3) 0.000(2) 0.004(3) C24 0.031(3) 0.046(3) 0.031(3) -0.006(2) -0.002(2) -0.004(2) C6 0.031(3) 0.041(3) 0.031(3) 0.001(2) 0.001(2) 0.000(2) C10 0.026(2) 0.034(3) 0.027(2) 0.000(2) 0.0021(19) 0.003(2) C5 0.026(2) 0.033(3) 0.038(3) 0.005(2) 0.008(2) 0.004(2) C18 0.041(3) 0.037(3) 0.029(3) 0.004(2) 0.004(2) 0.005(2) C17 0.028(2) 0.035(3) 0.029(2) -0.001(2) 0.0048(19) 0.002(2) O6 0.093(4) 0.101(4) 0.054(3) -0.005(3) 0.033(3) -0.015(3) C19 0.034(3) 0.037(3) 0.035(3) 0.007(2) 0.006(2) -0.003(2) C12 0.038(3) 0.041(3) 0.036(3) -0.001(2) 0.007(2) -0.001(2) C8 0.035(3) 0.036(3) 0.025(2) 0.004(2) 0.003(2) -0.004(2) C2 0.061(4) 0.037(4) 0.072(4) 0.003(3) 0.016(3) 0.010(3) O5 0.054(3) 0.114(5) 0.088(4) 0.032(3) -0.002(3) -0.032(3) O4 0.079(4) 0.085(4) 0.144(5) 0.069(4) 0.046(4) 0.017(3) C20 0.030(3) 0.061(4) 0.049(3) 0.011(3) 0.007(2) -0.003(3) C4 0.051(3) 0.041(4) 0.056(4) 0.003(3) 0.019(3) 0.007(3) C7 0.036(3) 0.039(3) 0.036(3) -0.002(2) 0.016(2) 0.000(2) C15 0.078(5) 0.045(4) 0.077(5) 0.011(3) 0.043(4) 0.011(3) C14 0.079(5) 0.050(4) 0.062(4) -0.005(3) 0.036(3) 0.013(4) C13 0.058(4) 0.038(4) 0.054(4) -0.008(3) 0.009(3) 0.007(3) C3 0.061(4) 0.042(4) 0.060(4) -0.004(3) 0.019(3) 0.010(3) O3W 0.056(3) 0.167(6) 0.078(4) 0.015(4) 0.008(3) -0.016(3) O7W 0.085(4) 0.110(5) 0.120(5) 0.049(4) 0.034(3) 0.023(3) O6W 0.094(4) 0.082(4) 0.125(5) -0.014(4) 0.022(4) -0.012(3) O5W 0.245(9) 0.115(6) 0.081(4) 0.012(4) 0.014(5) 0.098(6) O4W 0.178(8) 0.165(8) 0.089(5) -0.003(4) -0.014(5) 0.030(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 Lu1 O1W 2.243(4) . ? Lu1 O1 2.267(3) . ? Lu1 O2W 2.274(3) . ? Lu1 O8 2.321(3) . ? Lu1 O7 2.362(3) . ? Lu1 N3 2.435(5) 4_746 ? Lu1 N2 2.466(4) 4_746 ? Lu1 N1 2.493(4) 4_746 ? Lu1 C22 2.696(5) . ? S1 O2 1.445(4) . ? S1 O3 1.447(4) . ? S1 O1 1.471(3) . ? S1 C17 1.778(5) . ? S2 O5 1.408(5) . ? S2 O4 1.417(5) . ? S2 O6 1.463(5) . ? S2 C19 1.778(5) . ? O8 C22 1.274(6) . ? C1 N1 1.359(6) . ? C1 C2 1.376(8) . ? O7 C22 1.250(6) . ? N3 C11 1.341(6) . ? N3 C15 1.371(7) . ? N3 Lu1 2.435(5) 4_756 ? C23 C25 1.394(7) . ? C23 C24 1.394(7) . ? C23 C22 1.495(7) . ? N2 C10 1.340(6) . ? N2 C6 1.346(6) . ? N2 Lu1 2.466(4) 4_756 ? C11 C12 1.385(7) . ? C11 C10 1.477(7) . ? N1 C5 1.351(6) . ? N1 Lu1 2.493(4) 4_756 ? C16 C17 1.398(7) . ? C16 C21 1.406(7) . ? C16 C8 1.498(7) . ? C25 C24 1.377(7) 2_756 ? C9 C8 1.389(7) . ? C9 C10 1.397(6) . ? C21 C20 1.389(7) . ? C24 C25 1.377(7) 2_756 ? C6 C7 1.389(7) . ? C6 C5 1.484(7) . ? C5 C4 1.392(7) . ? C18 C17 1.379(6) . ? C18 C19 1.384(7) . ? C19 C20 1.365(7) . ? C12 C13 1.379(7) . ? C8 C7 1.373(7) . ? C2 C3 1.364(8) . ? C4 C3 1.357(8) . ? C15 C14 1.361(8) . ? C14 C13 1.383(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1W Lu1 O1 107.21(14) . . ? O1W Lu1 O2W 74.74(14) . . ? O1 Lu1 O2W 81.07(12) . . ? O1W Lu1 O8 154.78(15) . . ? O1 Lu1 O8 83.53(12) . . ? O2W Lu1 O8 130.19(13) . . ? O1W Lu1 O7 147.93(15) . . ? O1 Lu1 O7 77.31(13) . . ? O2W Lu1 O7 74.71(13) . . ? O8 Lu1 O7 55.72(12) . . ? O1W Lu1 N3 89.47(16) . 4_746 ? O1 Lu1 N3 151.75(13) . 4_746 ? O2W Lu1 N3 81.63(13) . 4_746 ? O8 Lu1 N3 90.82(13) . 4_746 ? O7 Lu1 N3 76.67(14) . 4_746 ? O1W Lu1 N2 80.31(14) . 4_746 ? O1 Lu1 N2 138.16(12) . 4_746 ? O2W Lu1 N2 138.92(13) . 4_746 ? O8 Lu1 N2 76.84(12) . 4_746 ? O7 Lu1 N2 118.12(13) . 4_746 ? N3 Lu1 N2 65.86(13) 4_746 4_746 ? O1W Lu1 N1 79.06(15) . 4_746 ? O1 Lu1 N1 75.29(12) . 4_746 ? O2W Lu1 N1 137.37(13) . 4_746 ? O8 Lu1 N1 81.91(13) . 4_746 ? O7 Lu1 N1 131.48(13) . 4_746 ? N3 Lu1 N1 131.40(13) 4_746 4_746 ? N2 Lu1 N1 65.69(13) 4_746 4_746 ? O1W Lu1 C22 173.18(16) . . ? O1 Lu1 C22 77.94(13) . . ? O2W Lu1 C22 102.08(15) . . ? O8 Lu1 C22 28.17(14) . . ? O7 Lu1 C22 27.61(14) . . ? N3 Lu1 C22 84.06(14) 4_746 . ? N2 Lu1 C22 98.92(14) 4_746 . ? N1 Lu1 C22 106.88(14) 4_746 . ? O2 S1 O3 114.6(2) . . ? O2 S1 O1 112.0(2) . . ? O3 S1 O1 111.3(2) . . ? O2 S1 C17 105.8(2) . . ? O3 S1 C17 106.8(2) . . ? O1 S1 C17 105.8(2) . . ? O5 S2 O4 115.6(4) . . ? O5 S2 O6 112.0(3) . . ? O4 S2 O6 110.6(4) . . ? O5 S2 C19 106.9(3) . . ? O4 S2 C19 106.0(3) . . ? O6 S2 C19 104.8(3) . . ? C22 O8 Lu1 92.5(3) . . ? N1 C1 C2 122.8(5) . . ? C22 O7 Lu1 91.3(3) . . ? C11 N3 C15 117.3(5) . . ? C11 N3 Lu1 121.4(3) . 4_756 ? C15 N3 Lu1 121.3(4) . 4_756 ? C25 C23 C24 119.6(5) . . ? C25 C23 C22 120.5(5) . . ? C24 C23 C22 119.7(5) . . ? C10 N2 C6 118.9(4) . . ? C10 N2 Lu1 120.0(3) . 4_756 ? C6 N2 Lu1 121.0(3) . 4_756 ? N3 C11 C12 121.6(5) . . ? N3 C11 C10 116.1(5) . . ? C12 C11 C10 122.3(5) . . ? S1 O1 Lu1 150.9(2) . . ? O7 C22 O8 120.3(5) . . ? O7 C22 C23 120.3(5) . . ? O8 C22 C23 119.4(5) . . ? O7 C22 Lu1 61.1(3) . . ? O8 C22 Lu1 59.3(2) . . ? C23 C22 Lu1 175.2(3) . . ? C5 N1 C1 117.2(4) . . ? C5 N1 Lu1 120.1(3) . 4_756 ? C1 N1 Lu1 122.6(3) . 4_756 ? C17 C16 C21 117.6(4) . . ? C17 C16 C8 125.1(4) . . ? C21 C16 C8 117.3(5) . . ? C24 C25 C23 120.4(5) 2_756 . ? C8 C9 C10 119.0(5) . . ? C20 C21 C16 121.3(5) . . ? C25 C24 C23 120.0(5) 2_756 . ? N2 C6 C7 121.5(5) . . ? N2 C6 C5 116.8(4) . . ? C7 C6 C5 121.7(5) . . ? N2 C10 C9 121.9(4) . . ? N2 C10 C11 116.4(4) . . ? C9 C10 C11 121.7(5) . . ? N1 C5 C4 121.0(5) . . ? N1 C5 C6 116.3(4) . . ? C4 C5 C6 122.7(4) . . ? C17 C18 C19 120.4(4) . . ? C18 C17 C16 120.6(4) . . ? C18 C17 S1 117.1(4) . . ? C16 C17 S1 122.2(4) . . ? C20 C19 C18 120.5(5) . . ? C20 C19 S2 120.0(4) . . ? C18 C19 S2 119.4(4) . . ? C13 C12 C11 120.8(5) . . ? C7 C8 C9 118.4(4) . . ? C7 C8 C16 119.5(4) . . ? C9 C8 C16 121.9(5) . . ? C3 C2 C1 119.6(6) . . ? C19 C20 C21 119.5(5) . . ? C3 C4 C5 121.0(5) . . ? C8 C7 C6 120.1(5) . . ? C14 C15 N3 123.0(6) . . ? C15 C14 C13 119.7(6) . . ? C12 C13 C14 117.6(6) . . ? C2 C3 C4 118.4(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.322 _refine_diff_density_min -0.838 _refine_diff_density_rms 0.126 _database_code_depnum_ccdc_archive 'CCDC 946696' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_19 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 Dy N3 O10 S2' _chemical_formula_weight 748.05 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.744(3) _cell_length_b 11.964(3) _cell_length_c 12.004(6) _cell_angle_alpha 109.647(4) _cell_angle_beta 103.175(4) _cell_angle_gamma 109.375(3) _cell_volume 1266.9(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2249 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.24 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.961 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 3.181 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5687 _exptl_absorpt_correction_T_max 0.6826 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6367 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4381 _reflns_number_gt 3745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0790P)^2^+0.9293P] 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 4381 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 Dy1 Dy 0.03310(3) 0.46520(3) 0.18194(3) 0.02191(14) Uani 1 1 d . . . S1 S 0.1954(2) 0.26722(19) 0.2514(2) 0.0354(5) Uani 1 1 d . . . S2 S 0.1577(2) -0.21778(17) 0.14336(18) 0.0281(4) Uani 1 1 d . . . O1 O 0.2099(8) 0.2215(6) 0.1303(6) 0.0559(18) Uani 1 1 d . . . O2 O 0.0927(6) 0.3239(5) 0.2509(5) 0.0336(12) Uani 1 1 d . . . O3 O 0.3277(6) 0.3525(6) 0.3617(7) 0.0562(18) Uani 1 1 d . . . O4 O 0.3104(6) -0.1488(6) 0.1965(6) 0.0496(16) Uani 1 1 d . . . O5 O 0.1005(6) -0.3230(5) 0.1783(5) 0.0365(13) Uani 1 1 d . . . O6 O 0.0971(6) -0.2618(5) 0.0059(5) 0.0349(13) Uani 1 1 d . . . O7 O -0.1848(6) 0.5339(5) -0.0789(5) 0.0344(12) Uani 1 1 d . . . O8 O -0.1658(6) 0.4774(6) 0.0799(6) 0.0405(14) Uani 1 1 d . . . N1 N 0.1731(7) 0.6455(6) 0.7607(6) 0.0300(14) Uani 1 1 d . . . N2 N -0.0274(6) 0.3995(6) 0.6108(6) 0.0263(13) Uani 1 1 d . . . N3 N -0.2740(7) 0.3665(6) 0.6367(6) 0.0294(14) Uani 1 1 d . . . C1 C 0.2672(9) 0.7741(8) 0.8317(8) 0.039(2) Uani 1 1 d . . . H1A H 0.2421 0.8297 0.8874 0.047 Uiso 1 1 calc R . . C2 C 0.3988(10) 0.8271(9) 0.8255(9) 0.046(2) Uani 1 1 d . . . H2A H 0.4610 0.9167 0.8758 0.055 Uiso 1 1 calc R . . C3 C 0.4370(9) 0.7457(8) 0.7440(8) 0.042(2) Uani 1 1 d . . . H3A H 0.5269 0.7785 0.7408 0.050 Uiso 1 1 calc R . . C4 C 0.3404(9) 0.6145(9) 0.6668(8) 0.039(2) Uani 1 1 d . . . H4A H 0.3629 0.5586 0.6085 0.047 Uiso 1 1 calc R . . C5 C 0.2095(8) 0.5672(7) 0.6772(7) 0.0269(16) Uani 1 1 d . . . C6 C 0.0971(8) 0.4251(8) 0.5926(7) 0.0311(17) Uani 1 1 d . . . C7 C 0.1220(9) 0.3326(8) 0.5102(7) 0.0317(17) Uani 1 1 d . . . H7A H 0.2123 0.3527 0.5075 0.038 Uiso 1 1 calc R . . C8 C 0.0089(9) 0.2069(7) 0.4299(7) 0.0333(18) Uani 1 1 d . . . C9 C -0.1231(9) 0.1814(8) 0.4390(7) 0.0344(18) Uani 1 1 d . . . H9A H -0.2012 0.0997 0.3841 0.041 Uiso 1 1 calc R . . C10 C -0.1385(9) 0.2791(7) 0.5310(7) 0.0311(17) Uani 1 1 d . . . C11 C -0.2760(8) 0.2598(7) 0.5457(7) 0.0306(17) Uani 1 1 d . . . C12 C -0.4011(9) 0.1437(8) 0.4679(8) 0.041(2) Uani 1 1 d . . . H12A H -0.3993 0.0714 0.4081 0.049 Uiso 1 1 calc R . . C13 C -0.5281(10) 0.1360(9) 0.4796(9) 0.049(2) Uani 1 1 d . . . H13A H -0.6131 0.0592 0.4276 0.058 Uiso 1 1 calc R . . C14 C -0.5257(9) 0.2446(9) 0.5699(9) 0.047(2) Uani 1 1 d . . . H14A H -0.6099 0.2424 0.5792 0.056 Uiso 1 1 calc R . . C15 C -0.3984(9) 0.3569(8) 0.6467(8) 0.0389(19) Uani 1 1 d . . . H15A H -0.3989 0.4290 0.7081 0.047 Uiso 1 1 calc R . . C16 C 0.0350(9) 0.1028(7) 0.3426(7) 0.0313(17) Uani 1 1 d . . . C17 C 0.1172(8) 0.1196(7) 0.2695(7) 0.0291(17) Uani 1 1 d . . . C18 C 0.1478(8) 0.0186(7) 0.2054(8) 0.0327(17) Uani 1 1 d . . . H18A H 0.2026 0.0307 0.1568 0.039 Uiso 1 1 calc R . . C19 C 0.0974(8) -0.1011(7) 0.2129(7) 0.0275(16) Uani 1 1 d . . . C20 C 0.0094(10) -0.1223(8) 0.2771(8) 0.041(2) Uani 1 1 d . . . H20A H -0.0280 -0.2037 0.2787 0.049 Uiso 1 1 calc R . . C21 C -0.0245(10) -0.0238(8) 0.3397(8) 0.042(2) Uani 1 1 d . . . H21A H -0.0873 -0.0405 0.3806 0.050 Uiso 1 1 calc R . . C22 C -0.2285(8) 0.5064(7) 0.0009(7) 0.0262(16) Uani 1 1 d . . . C23 C -0.3698(8) 0.5035(7) 0.0001(7) 0.0259(15) Uani 1 1 d . . . C24 C -0.4235(8) 0.5722(8) -0.0508(8) 0.0362(19) Uani 1 1 d . . . H24A H -0.3723 0.6216 -0.0847 0.043 Uiso 1 1 calc R . . O1W O 0.4017(9) 0.1195(8) 0.7782(9) 0.101(3) Uani 1 1 d . . . H1WA H 0.4135 0.1990 0.8164 0.152 Uiso 1 1 d R . . H1WB H 0.4852 0.1237 0.7903 0.152 Uiso 1 1 d R . . O2W O 0.2651(14) 0.0620(11) 0.9418(12) 0.144(5) Uani 1 1 d . . . H2WA H 0.1837 0.0099 0.8851 0.216 Uiso 1 1 d R . . H2WB H 0.2603 0.1256 0.9967 0.216 Uiso 1 1 d R . . C25 C -0.4449(8) 0.4320(8) 0.0519(8) 0.0360(19) Uani 1 1 d . . . H25A H -0.4078 0.3864 0.0877 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Dy1 0.0252(2) 0.0199(2) 0.0297(2) 0.01416(15) 0.01404(15) 0.01474(15) S1 0.0442(12) 0.0273(10) 0.0565(13) 0.0273(10) 0.0293(11) 0.0247(9) S2 0.0350(10) 0.0199(9) 0.0335(10) 0.0117(8) 0.0130(8) 0.0171(8) O1 0.092(5) 0.049(4) 0.077(5) 0.047(4) 0.065(4) 0.047(4) O2 0.043(3) 0.032(3) 0.048(3) 0.026(3) 0.024(3) 0.028(3) O3 0.038(4) 0.042(4) 0.095(5) 0.036(4) 0.024(4) 0.020(3) O4 0.037(3) 0.043(4) 0.063(4) 0.015(3) 0.015(3) 0.023(3) O5 0.058(4) 0.023(3) 0.042(3) 0.021(2) 0.021(3) 0.024(3) O6 0.045(3) 0.029(3) 0.033(3) 0.012(2) 0.018(3) 0.018(3) O7 0.037(3) 0.036(3) 0.048(3) 0.026(3) 0.028(3) 0.023(3) O8 0.032(3) 0.053(4) 0.066(4) 0.044(3) 0.025(3) 0.029(3) N1 0.037(4) 0.026(3) 0.032(3) 0.015(3) 0.017(3) 0.016(3) N2 0.036(4) 0.022(3) 0.032(3) 0.016(3) 0.018(3) 0.018(3) N3 0.033(4) 0.028(3) 0.031(3) 0.014(3) 0.014(3) 0.016(3) C1 0.046(5) 0.027(4) 0.051(5) 0.018(4) 0.025(4) 0.019(4) C2 0.043(5) 0.033(5) 0.054(6) 0.017(4) 0.020(4) 0.012(4) C3 0.033(4) 0.046(5) 0.049(5) 0.026(4) 0.019(4) 0.013(4) C4 0.041(5) 0.043(5) 0.052(5) 0.030(4) 0.029(4) 0.022(4) C5 0.036(4) 0.027(4) 0.033(4) 0.022(3) 0.022(3) 0.018(3) C6 0.029(4) 0.035(4) 0.038(4) 0.027(4) 0.011(3) 0.015(3) C7 0.038(4) 0.035(4) 0.042(5) 0.024(4) 0.025(4) 0.024(4) C8 0.048(5) 0.026(4) 0.035(4) 0.014(3) 0.020(4) 0.024(4) C9 0.048(5) 0.028(4) 0.034(4) 0.013(4) 0.018(4) 0.024(4) C10 0.045(5) 0.021(4) 0.037(4) 0.017(3) 0.020(4) 0.018(3) C11 0.035(4) 0.033(4) 0.037(4) 0.021(4) 0.019(4) 0.021(4) C12 0.046(5) 0.027(4) 0.046(5) 0.014(4) 0.021(4) 0.013(4) C13 0.044(5) 0.041(5) 0.047(5) 0.017(4) 0.014(4) 0.009(4) C14 0.030(5) 0.053(6) 0.054(6) 0.022(5) 0.013(4) 0.018(4) C15 0.038(5) 0.041(5) 0.043(5) 0.019(4) 0.016(4) 0.023(4) C16 0.045(5) 0.023(4) 0.038(4) 0.016(3) 0.023(4) 0.021(4) C17 0.038(4) 0.019(4) 0.036(4) 0.014(3) 0.014(4) 0.017(3) C18 0.038(4) 0.027(4) 0.042(5) 0.016(4) 0.020(4) 0.021(3) C19 0.036(4) 0.023(4) 0.028(4) 0.010(3) 0.012(3) 0.020(3) C20 0.065(6) 0.034(5) 0.052(5) 0.031(4) 0.040(5) 0.030(4) C21 0.056(5) 0.039(5) 0.050(5) 0.024(4) 0.038(5) 0.028(4) C22 0.026(4) 0.021(4) 0.035(4) 0.012(3) 0.014(3) 0.013(3) C23 0.028(4) 0.030(4) 0.031(4) 0.017(3) 0.015(3) 0.020(3) C24 0.031(4) 0.043(5) 0.060(5) 0.037(4) 0.029(4) 0.022(4) O1W 0.083(6) 0.073(6) 0.120(8) 0.016(6) 0.045(6) 0.029(5) O2W 0.151(11) 0.104(9) 0.153(11) 0.028(8) 0.052(9) 0.065(8) C25 0.040(5) 0.046(5) 0.059(5) 0.042(4) 0.033(4) 0.032(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 Dy1 O7 2.259(5) 2_565 ? Dy1 O8 2.285(5) . ? Dy1 O2 2.318(5) . ? Dy1 O6 2.362(5) 2 ? Dy1 O5 2.413(5) 1_565 ? Dy1 N2 2.498(6) 2_566 ? Dy1 N1 2.549(6) 2_566 ? Dy1 N3 2.553(6) 2_566 ? S1 O1 1.436(6) . ? S1 O3 1.444(7) . ? S1 O2 1.474(5) . ? S1 C17 1.796(7) . ? S2 O4 1.431(6) . ? S2 O5 1.448(5) . ? S2 O6 1.457(6) . ? S2 C19 1.769(7) . ? O5 Dy1 2.413(5) 1_545 ? O6 Dy1 2.362(5) 2 ? O7 C22 1.249(9) . ? O7 Dy1 2.259(5) 2_565 ? O8 C22 1.249(9) . ? N1 C1 1.345(10) . ? N1 C5 1.351(9) . ? N1 Dy1 2.549(6) 2_566 ? N2 C10 1.352(10) . ? N2 C6 1.355(9) . ? N2 Dy1 2.498(6) 2_566 ? N3 C15 1.340(10) . ? N3 C11 1.362(9) . ? N3 Dy1 2.553(6) 2_566 ? C1 C2 1.376(12) . ? C1 H1A 0.9300 . ? C2 C3 1.371(12) . ? C2 H2A 0.9300 . ? C3 C4 1.379(12) . ? C3 H3A 0.9300 . ? C4 C5 1.383(10) . ? C4 H4A 0.9300 . ? C5 C6 1.515(11) . ? C6 C7 1.363(11) . ? C7 C8 1.394(11) . ? C7 H7A 0.9300 . ? C8 C9 1.388(11) . ? C8 C16 1.488(10) . ? C9 C10 1.398(10) . ? C9 H9A 0.9300 . ? C10 C11 1.479(11) . ? C11 C12 1.387(11) . ? C12 C13 1.379(13) . ? C12 H12A 0.9300 . ? C13 C14 1.371(13) . ? C13 H13A 0.9300 . ? C14 C15 1.378(12) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.395(10) . ? C16 C21 1.420(11) . ? C17 C18 1.383(10) . ? C18 C19 1.396(10) . ? C18 H18A 0.9300 . ? C19 C20 1.363(11) . ? C20 C21 1.379(11) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 C23 1.505(10) . ? C23 C24 1.369(10) . ? C23 C25 1.378(10) . ? C24 C25 1.395(10) 2_465 ? C24 H24A 0.9300 . ? O1W H1WA 0.8555 . ? O1W H1WB 0.8565 . ? O2W H2WA 0.8361 . ? O2W H2WB 0.8493 . ? C25 C24 1.395(10) 2_465 ? C25 H25A 0.9300 . ? 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 O7 Dy1 O8 114.3(2) 2_565 . ? O7 Dy1 O2 89.11(18) 2_565 . ? O8 Dy1 O2 139.26(19) . . ? O7 Dy1 O6 76.53(19) 2_565 2 ? O8 Dy1 O6 75.4(2) . 2 ? O2 Dy1 O6 78.68(19) . 2 ? O7 Dy1 O5 77.68(19) 2_565 1_565 ? O8 Dy1 O5 70.3(2) . 1_565 ? O2 Dy1 O5 150.2(2) . 1_565 ? O6 Dy1 O5 122.70(19) 2 1_565 ? O7 Dy1 N2 139.8(2) 2_565 2_566 ? O8 Dy1 N2 87.9(2) . 2_566 ? O2 Dy1 N2 94.77(19) . 2_566 ? O6 Dy1 N2 143.40(19) 2 2_566 ? O5 Dy1 N2 79.46(18) 1_565 2_566 ? O7 Dy1 N1 154.2(2) 2_565 2_566 ? O8 Dy1 N1 69.9(2) . 2_566 ? O2 Dy1 N1 75.22(19) . 2_566 ? O6 Dy1 N1 80.37(19) 2 2_566 ? O5 Dy1 N1 125.29(19) 1_565 2_566 ? N2 Dy1 N1 63.24(19) 2_566 2_566 ? O7 Dy1 N3 78.0(2) 2_565 2_566 ? O8 Dy1 N3 134.6(2) . 2_566 ? O2 Dy1 N3 80.8(2) . 2_566 ? O6 Dy1 N3 147.3(2) 2 2_566 ? O5 Dy1 N3 70.4(2) 1_565 2_566 ? N2 Dy1 N3 63.34(19) 2_566 2_566 ? N1 Dy1 N3 118.3(2) 2_566 2_566 ? O1 S1 O3 115.4(4) . . ? O1 S1 O2 112.3(4) . . ? O3 S1 O2 112.0(4) . . ? O1 S1 C17 104.6(4) . . ? O3 S1 C17 105.6(4) . . ? O2 S1 C17 106.0(3) . . ? O4 S2 O5 113.9(4) . . ? O4 S2 O6 112.8(4) . . ? O5 S2 O6 112.3(3) . . ? O4 S2 C19 106.3(4) . . ? O5 S2 C19 104.9(3) . . ? O6 S2 C19 105.8(3) . . ? S1 O2 Dy1 139.6(3) . . ? S2 O5 Dy1 160.1(3) . 1_545 ? S2 O6 Dy1 137.4(3) . 2 ? C22 O7 Dy1 148.3(5) . 2_565 ? C22 O8 Dy1 149.9(5) . . ? C1 N1 C5 117.7(7) . . ? C1 N1 Dy1 122.1(5) . 2_566 ? C5 N1 Dy1 118.2(5) . 2_566 ? C10 N2 C6 117.4(6) . . ? C10 N2 Dy1 119.1(5) . 2_566 ? C6 N2 Dy1 120.9(5) . 2_566 ? C15 N3 C11 117.6(7) . . ? C15 N3 Dy1 122.6(5) . 2_566 ? C11 N3 Dy1 116.7(5) . 2_566 ? N1 C1 C2 123.0(8) . . ? N1 C1 H1A 118.5 . . ? C2 C1 H1A 118.5 . . ? C3 C2 C1 118.9(8) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 119.2(8) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C3 C4 C5 119.1(8) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? N1 C5 C4 122.1(7) . . ? N1 C5 C6 116.2(6) . . ? C4 C5 C6 121.7(7) . . ? N2 C6 C7 124.0(7) . . ? N2 C6 C5 113.2(7) . . ? C7 C6 C5 122.8(7) . . ? C6 C7 C8 118.5(7) . . ? C6 C7 H7A 120.7 . . ? C8 C7 H7A 120.7 . . ? C9 C8 C7 118.4(7) . . ? C9 C8 C16 122.1(7) . . ? C7 C8 C16 119.4(7) . . ? C8 C9 C10 119.8(7) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? N2 C10 C9 121.4(7) . . ? N2 C10 C11 115.7(6) . . ? C9 C10 C11 122.9(7) . . ? N3 C11 C12 121.6(7) . . ? N3 C11 C10 115.6(7) . . ? C12 C11 C10 122.7(7) . . ? C13 C12 C11 119.8(8) . . ? C13 C12 H12A 120.1 . . ? C11 C12 H12A 120.1 . . ? C14 C13 C12 118.2(8) . . ? C14 C13 H13A 120.9 . . ? C12 C13 H13A 120.9 . . ? C13 C14 C15 119.9(8) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? N3 C15 C14 122.8(8) . . ? N3 C15 H15A 118.6 . . ? C14 C15 H15A 118.6 . . ? C17 C16 C21 117.6(7) . . ? C17 C16 C8 126.4(7) . . ? C21 C16 C8 115.9(7) . . ? C18 C17 C16 120.2(7) . . ? C18 C17 S1 114.1(6) . . ? C16 C17 S1 125.7(5) . . ? C17 C18 C19 120.8(7) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C20 C19 C18 119.8(7) . . ? C20 C19 S2 122.3(6) . . ? C18 C19 S2 117.9(6) . . ? C19 C20 C21 120.3(7) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C20 C21 C16 121.0(7) . . ? C20 C21 H21A 119.5 . . ? C16 C21 H21A 119.5 . . ? O8 C22 O7 125.2(7) . . ? O8 C22 C23 116.8(6) . . ? O7 C22 C23 118.0(7) . . ? C24 C23 C25 119.9(7) . . ? C24 C23 C22 120.4(7) . . ? C25 C23 C22 119.7(7) . . ? C23 C24 C25 119.9(7) . 2_465 ? C23 C24 H24A 120.0 . . ? C25 C24 H24A 120.0 2_465 . ? H1WA O1W H1WB 106.6 . . ? H2WA O2W H2WB 109.1 . . ? C23 C25 C24 120.1(7) . 2_465 ? C23 C25 H25A 119.9 . . ? C24 C25 H25A 119.9 2_465 . ? 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 S1 O2 Dy1 -44.2(6) . . . . ? O3 S1 O2 Dy1 87.6(6) . . . . ? C17 S1 O2 Dy1 -157.8(5) . . . . ? O7 Dy1 O2 S1 8.2(5) 2_565 . . . ? O8 Dy1 O2 S1 135.9(5) . . . . ? O6 Dy1 O2 S1 84.6(5) 2 . . . ? O5 Dy1 O2 S1 -54.7(7) 1_565 . . . ? N2 Dy1 O2 S1 -131.8(5) 2_566 . . . ? N1 Dy1 O2 S1 167.5(6) 2_566 . . . ? N3 Dy1 O2 S1 -69.8(5) 2_566 . . . ? O4 S2 O5 Dy1 -75.9(11) . . . 1_545 ? O6 S2 O5 Dy1 53.9(12) . . . 1_545 ? C19 S2 O5 Dy1 168.3(10) . . . 1_545 ? O4 S2 O6 Dy1 114.5(5) . . . 2 ? O5 S2 O6 Dy1 -15.8(6) . . . 2 ? C19 S2 O6 Dy1 -129.7(5) . . . 2 ? O7 Dy1 O8 C22 -20.4(11) 2_565 . . . ? O2 Dy1 O8 C22 -140.2(10) . . . . ? O6 Dy1 O8 C22 -87.9(11) 2 . . . ? O5 Dy1 O8 C22 45.4(11) 1_565 . . . ? N2 Dy1 O8 C22 125.0(11) 2_566 . . . ? N1 Dy1 O8 C22 -172.8(11) 2_566 . . . ? N3 Dy1 O8 C22 76.8(11) 2_566 . . . ? C5 N1 C1 C2 -2.2(12) . . . . ? Dy1 N1 C1 C2 161.4(7) 2_566 . . . ? N1 C1 C2 C3 -0.3(14) . . . . ? C1 C2 C3 C4 2.7(14) . . . . ? C2 C3 C4 C5 -2.5(13) . . . . ? C1 N1 C5 C4 2.3(11) . . . . ? Dy1 N1 C5 C4 -161.9(6) 2_566 . . . ? C1 N1 C5 C6 -176.1(7) . . . . ? Dy1 N1 C5 C6 19.7(8) 2_566 . . . ? C3 C4 C5 N1 0.0(12) . . . . ? C3 C4 C5 C6 178.3(7) . . . . ? C10 N2 C6 C7 -8.3(11) . . . . ? Dy1 N2 C6 C7 153.1(6) 2_566 . . . ? C10 N2 C6 C5 173.7(6) . . . . ? Dy1 N2 C6 C5 -24.9(8) 2_566 . . . ? N1 C5 C6 N2 2.6(9) . . . . ? C4 C5 C6 N2 -175.8(7) . . . . ? N1 C5 C6 C7 -175.4(7) . . . . ? C4 C5 C6 C7 6.2(11) . . . . ? N2 C6 C7 C8 6.7(12) . . . . ? C5 C6 C7 C8 -175.6(7) . . . . ? C6 C7 C8 C9 -0.9(11) . . . . ? C6 C7 C8 C16 -177.7(7) . . . . ? C7 C8 C9 C10 -2.7(12) . . . . ? C16 C8 C9 C10 174.0(7) . . . . ? C6 N2 C10 C9 4.3(11) . . . . ? Dy1 N2 C10 C9 -157.5(6) 2_566 . . . ? C6 N2 C10 C11 -174.2(6) . . . . ? Dy1 N2 C10 C11 24.0(8) 2_566 . . . ? C8 C9 C10 N2 1.0(12) . . . . ? C8 C9 C10 C11 179.4(7) . . . . ? C15 N3 C11 C12 -1.7(11) . . . . ? Dy1 N3 C11 C12 159.1(6) 2_566 . . . ? C15 N3 C11 C10 175.1(7) . . . . ? Dy1 N3 C11 C10 -24.2(8) 2_566 . . . ? N2 C10 C11 N3 0.8(10) . . . . ? C9 C10 C11 N3 -177.7(7) . . . . ? N2 C10 C11 C12 177.5(7) . . . . ? C9 C10 C11 C12 -1.0(12) . . . . ? N3 C11 C12 C13 1.8(13) . . . . ? C10 C11 C12 C13 -174.6(8) . . . . ? C11 C12 C13 C14 -0.6(14) . . . . ? C12 C13 C14 C15 -0.7(14) . . . . ? C11 N3 C15 C14 0.3(12) . . . . ? Dy1 N3 C15 C14 -159.2(7) 2_566 . . . ? C13 C14 C15 N3 0.8(14) . . . . ? C9 C8 C16 C17 140.6(9) . . . . ? C7 C8 C16 C17 -42.8(12) . . . . ? C9 C8 C16 C21 -42.8(11) . . . . ? C7 C8 C16 C21 133.8(8) . . . . ? C21 C16 C17 C18 -5.1(12) . . . . ? C8 C16 C17 C18 171.5(8) . . . . ? C21 C16 C17 S1 176.6(6) . . . . ? C8 C16 C17 S1 -6.9(12) . . . . ? O1 S1 C17 C18 27.2(7) . . . . ? O3 S1 C17 C18 -95.0(7) . . . . ? O2 S1 C17 C18 146.0(6) . . . . ? O1 S1 C17 C16 -154.4(7) . . . . ? O3 S1 C17 C16 83.4(8) . . . . ? O2 S1 C17 C16 -35.5(8) . . . . ? C16 C17 C18 C19 -0.1(12) . . . . ? S1 C17 C18 C19 178.5(6) . . . . ? C17 C18 C19 C20 4.3(12) . . . . ? C17 C18 C19 S2 -173.0(6) . . . . ? O4 S2 C19 C20 -124.2(7) . . . . ? O5 S2 C19 C20 -3.2(8) . . . . ? O6 S2 C19 C20 115.7(7) . . . . ? O4 S2 C19 C18 53.0(7) . . . . ? O5 S2 C19 C18 174.0(6) . . . . ? O6 S2 C19 C18 -67.1(7) . . . . ? C18 C19 C20 C21 -3.1(13) . . . . ? S2 C19 C20 C21 174.1(7) . . . . ? C19 C20 C21 C16 -2.2(14) . . . . ? C17 C16 C21 C20 6.3(13) . . . . ? C8 C16 C21 C20 -170.6(9) . . . . ? Dy1 O8 C22 O7 11.4(16) . . . . ? Dy1 O8 C22 C23 -170.5(7) . . . . ? Dy1 O7 C22 O8 13.6(15) 2_565 . . . ? Dy1 O7 C22 C23 -164.5(6) 2_565 . . . ? O8 C22 C23 C24 159.0(7) . . . . ? O7 C22 C23 C24 -22.8(11) . . . . ? O8 C22 C23 C25 -20.5(11) . . . . ? O7 C22 C23 C25 157.7(7) . . . . ? C25 C23 C24 C25 -1.0(14) . . . 2_465 ? C22 C23 C24 C25 179.5(7) . . . 2_465 ? C24 C23 C25 C24 1.0(14) . . . 2_465 ? C22 C23 C25 C24 -179.5(7) . . . 2_465 ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 2.987 _refine_diff_density_min -1.748 _refine_diff_density_rms 0.186 _database_code_depnum_ccdc_archive 'CCDC 946697' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_20 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 Er N3 O10 S2' _chemical_formula_weight 752.81 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7213(10) _cell_length_b 11.9418(11) _cell_length_c 11.9667(11) _cell_angle_alpha 109.7400(10) _cell_angle_beta 103.1380(10) _cell_angle_gamma 109.2170(10) _cell_volume 1259.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2933 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.11 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.986 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 3.566 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5076 _exptl_absorpt_correction_T_max 0.6168 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7533 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5315 _reflns_number_gt 4710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0390P)^2^+0.7375P] 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 5315 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0824 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Er1 Er 0.03341(2) 0.46517(2) 0.18176(2) 0.01765(8) Uani 1 1 d . . . S1 S 0.19412(15) 0.26720(13) 0.25078(14) 0.0297(3) Uani 1 1 d . . . S2 S 0.15800(13) -0.21879(12) 0.14271(12) 0.0225(3) Uani 1 1 d . . . O1 O 0.2097(5) 0.2216(4) 0.1295(4) 0.0499(12) Uani 1 1 d . . . O2 O 0.0917(4) 0.3238(4) 0.2504(3) 0.0288(8) Uani 1 1 d . . . O3 O 0.3265(4) 0.3526(4) 0.3612(5) 0.0495(12) Uani 1 1 d . . . O4 O 0.3113(4) -0.1485(4) 0.1958(4) 0.0436(11) Uani 1 1 d . . . O5 O 0.1016(4) -0.3236(4) 0.1794(4) 0.0304(8) Uani 1 1 d . . . O6 O 0.0963(4) -0.2636(4) 0.0045(3) 0.0303(8) Uani 1 1 d . . . O7 O -0.1829(4) 0.5361(4) -0.0778(3) 0.0284(8) Uani 1 1 d . . . O8 O -0.1636(4) 0.4790(4) 0.0815(4) 0.0340(9) Uani 1 1 d . . . N1 N 0.1729(4) 0.6471(4) 0.7623(4) 0.0239(9) Uani 1 1 d . . . N2 N -0.0290(4) 0.4002(4) 0.6130(4) 0.0228(9) Uani 1 1 d . . . N3 N -0.2745(4) 0.3674(4) 0.6385(4) 0.0258(9) Uani 1 1 d . . . C1 C 0.2662(6) 0.7734(6) 0.8316(6) 0.0349(13) Uani 1 1 d . . . H1A H 0.2412 0.8292 0.8878 0.042 Uiso 1 1 calc R . . C2 C 0.3980(6) 0.8275(6) 0.8257(6) 0.0397(14) Uani 1 1 d . . . H2A H 0.4594 0.9173 0.8759 0.048 Uiso 1 1 calc R . . C3 C 0.4366(6) 0.7459(6) 0.7440(6) 0.0375(14) Uani 1 1 d . . . H3A H 0.5264 0.7790 0.7404 0.045 Uiso 1 1 calc R . . C4 C 0.3410(6) 0.6142(6) 0.6673(5) 0.0305(12) Uani 1 1 d . . . H4A H 0.3645 0.5582 0.6097 0.037 Uiso 1 1 calc R . . C5 C 0.2076(5) 0.5657(5) 0.6774(5) 0.0236(11) Uani 1 1 d . . . C6 C 0.0969(5) 0.4280(5) 0.5976(5) 0.0249(11) Uani 1 1 d . . . C7 C 0.1191(6) 0.3328(5) 0.5095(5) 0.0283(11) Uani 1 1 d . . . H7A H 0.2082 0.3531 0.5038 0.034 Uiso 1 1 calc R . . C8 C 0.0080(6) 0.2089(5) 0.4313(5) 0.0273(11) Uani 1 1 d . . . C9 C -0.1253(6) 0.1814(5) 0.4394(5) 0.0282(11) Uani 1 1 d . . . H9A H -0.2030 0.0993 0.3846 0.034 Uiso 1 1 calc R . . C10 C -0.1397(5) 0.2797(5) 0.5313(5) 0.0236(10) Uani 1 1 d . . . C11 C -0.2781(5) 0.2612(5) 0.5475(5) 0.0232(10) Uani 1 1 d . . . C12 C -0.4028(6) 0.1450(6) 0.4692(5) 0.0352(13) Uani 1 1 d . . . H12A H -0.4016 0.0728 0.4080 0.042 Uiso 1 1 calc R . . C13 C -0.5286(6) 0.1383(6) 0.4838(6) 0.0440(15) Uani 1 1 d . . . H13A H -0.6132 0.0606 0.4343 0.053 Uiso 1 1 calc R . . C14 C -0.5270(6) 0.2489(6) 0.5734(6) 0.0402(15) Uani 1 1 d . . . H14A H -0.6110 0.2488 0.5823 0.048 Uiso 1 1 calc R . . C15 C -0.3976(6) 0.3594(6) 0.6493(6) 0.0351(13) Uani 1 1 d . . . H15A H -0.3963 0.4325 0.7115 0.042 Uiso 1 1 calc R . . C16 C 0.0324(6) 0.1026(5) 0.3427(5) 0.0274(11) Uani 1 1 d . . . C17 C 0.1152(5) 0.1188(5) 0.2690(5) 0.0220(10) Uani 1 1 d . . . C18 C 0.1461(5) 0.0177(5) 0.2040(5) 0.0234(10) Uani 1 1 d . . . H18A H 0.2008 0.0298 0.1551 0.028 Uiso 1 1 calc R . . C19 C 0.0960(5) -0.1019(5) 0.2113(5) 0.0220(10) Uani 1 1 d . . . C20 C 0.0065(6) -0.1242(5) 0.2758(5) 0.0318(12) Uani 1 1 d . . . H20A H -0.0324 -0.2059 0.2766 0.038 Uiso 1 1 calc R . . C21 C -0.0249(6) -0.0224(6) 0.3398(5) 0.0358(13) Uani 1 1 d . . . H21A H -0.0865 -0.0381 0.3823 0.043 Uiso 1 1 calc R . . C22 C -0.2280(5) 0.5065(5) 0.0024(5) 0.0231(10) Uani 1 1 d . . . C23 C -0.3692(5) 0.5041(5) 0.0003(5) 0.0220(10) Uani 1 1 d . . . C24 C -0.4230(5) 0.5745(6) -0.0501(5) 0.0294(12) Uani 1 1 d . . . H24A H -0.3715 0.6249 -0.0831 0.035 Uiso 1 1 calc R . . O1W O 0.4010(6) 0.1184(6) 0.7780(6) 0.098(2) Uani 1 1 d . . . H1WA H 0.4128 0.1979 0.8162 0.147 Uiso 1 1 d R . . H1WB H 0.4845 0.1226 0.7902 0.147 Uiso 1 1 d R . . O2W O 0.2671(10) 0.0629(9) 0.9424(8) 0.157(4) Uani 1 1 d . . . H2WA H 0.1857 0.0107 0.8856 0.235 Uiso 1 1 d R . . H2WB H 0.2623 0.1265 0.9973 0.235 Uiso 1 1 d R . . C25 C -0.4460(6) 0.4305(6) 0.0510(6) 0.0319(13) Uani 1 1 d . . . H25A H -0.4090 0.3842 0.0860 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Er1 0.01973(12) 0.01766(12) 0.01875(12) 0.00800(9) 0.00970(9) 0.01043(9) S1 0.0359(7) 0.0245(7) 0.0450(8) 0.0218(7) 0.0248(7) 0.0191(6) S2 0.0283(6) 0.0161(6) 0.0214(6) 0.0052(5) 0.0092(5) 0.0115(5) O1 0.088(3) 0.042(3) 0.069(3) 0.040(3) 0.064(3) 0.045(3) O2 0.037(2) 0.031(2) 0.033(2) 0.0197(18) 0.0173(17) 0.0221(18) O3 0.029(2) 0.037(3) 0.072(3) 0.025(2) 0.009(2) 0.0096(19) O4 0.026(2) 0.036(2) 0.055(3) 0.011(2) 0.0091(19) 0.0119(18) O5 0.043(2) 0.0225(19) 0.034(2) 0.0151(17) 0.0166(18) 0.0192(17) O6 0.039(2) 0.026(2) 0.0216(19) 0.0061(17) 0.0134(17) 0.0120(17) O7 0.0273(19) 0.036(2) 0.030(2) 0.0169(18) 0.0187(16) 0.0161(17) O8 0.0245(19) 0.050(3) 0.046(2) 0.033(2) 0.0170(18) 0.0231(19) N1 0.027(2) 0.022(2) 0.023(2) 0.0108(19) 0.0110(18) 0.0098(19) N2 0.029(2) 0.022(2) 0.021(2) 0.0094(19) 0.0131(18) 0.0130(19) N3 0.028(2) 0.025(2) 0.026(2) 0.011(2) 0.0118(19) 0.0126(19) C1 0.040(3) 0.028(3) 0.039(3) 0.013(3) 0.023(3) 0.015(3) C2 0.036(3) 0.034(3) 0.036(3) 0.011(3) 0.012(3) 0.006(3) C3 0.025(3) 0.047(4) 0.039(3) 0.023(3) 0.014(3) 0.009(3) C4 0.033(3) 0.039(3) 0.031(3) 0.019(3) 0.019(2) 0.021(3) C5 0.028(3) 0.028(3) 0.025(3) 0.017(2) 0.015(2) 0.016(2) C6 0.031(3) 0.027(3) 0.029(3) 0.019(2) 0.017(2) 0.017(2) C7 0.036(3) 0.030(3) 0.025(3) 0.011(2) 0.015(2) 0.021(3) C8 0.046(3) 0.024(3) 0.022(3) 0.012(2) 0.016(2) 0.022(3) C9 0.036(3) 0.020(3) 0.025(3) 0.006(2) 0.010(2) 0.012(2) C10 0.030(3) 0.025(3) 0.019(2) 0.011(2) 0.010(2) 0.014(2) C11 0.030(3) 0.024(3) 0.017(2) 0.010(2) 0.009(2) 0.012(2) C12 0.036(3) 0.031(3) 0.029(3) 0.010(3) 0.009(3) 0.009(3) C13 0.032(3) 0.036(4) 0.041(4) 0.011(3) 0.004(3) 0.002(3) C14 0.023(3) 0.050(4) 0.048(4) 0.024(3) 0.012(3) 0.015(3) C15 0.031(3) 0.037(3) 0.034(3) 0.011(3) 0.011(3) 0.019(3) C16 0.037(3) 0.023(3) 0.026(3) 0.012(2) 0.014(2) 0.013(2) C17 0.027(3) 0.017(2) 0.024(3) 0.009(2) 0.012(2) 0.010(2) C18 0.029(3) 0.022(3) 0.025(3) 0.013(2) 0.015(2) 0.013(2) C19 0.030(3) 0.016(2) 0.019(2) 0.005(2) 0.009(2) 0.012(2) C20 0.049(3) 0.023(3) 0.033(3) 0.015(3) 0.025(3) 0.019(3) C21 0.052(4) 0.042(3) 0.032(3) 0.023(3) 0.031(3) 0.026(3) C22 0.022(2) 0.022(3) 0.026(3) 0.009(2) 0.010(2) 0.012(2) C23 0.020(2) 0.030(3) 0.027(3) 0.017(2) 0.015(2) 0.016(2) C24 0.027(3) 0.039(3) 0.041(3) 0.028(3) 0.022(2) 0.019(2) O1W 0.078(4) 0.079(5) 0.102(5) 0.010(4) 0.033(4) 0.028(4) O2W 0.183(9) 0.155(9) 0.116(7) 0.022(6) 0.059(6) 0.095(8) C25 0.032(3) 0.048(4) 0.047(3) 0.040(3) 0.023(3) 0.029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Er1 O7 2.242(3) 2_565 ? Er1 O8 2.267(3) . ? Er1 O2 2.306(3) . ? Er1 O6 2.336(4) 2 ? Er1 O5 2.396(3) 1_565 ? Er1 N2 2.461(4) 2_566 ? Er1 N1 2.543(4) 2_566 ? Er1 N3 2.544(4) 2_566 ? S1 O1 1.437(4) . ? S1 O3 1.444(4) . ? S1 O2 1.466(4) . ? S1 C17 1.806(5) . ? S2 O4 1.437(4) . ? S2 O5 1.455(4) . ? S2 O6 1.460(4) . ? S2 C19 1.774(5) . ? O5 Er1 2.396(3) 1_545 ? O6 Er1 2.336(4) 2 ? O7 C22 1.268(6) . ? O7 Er1 2.242(3) 2_565 ? O8 C22 1.243(6) . ? N1 C1 1.322(7) . ? N1 C5 1.363(6) . ? N1 Er1 2.543(4) 2_566 ? N2 C10 1.354(6) . ? N2 C6 1.351(6) . ? N2 Er1 2.461(4) 2_566 ? N3 C15 1.330(7) . ? N3 C11 1.346(6) . ? N3 Er1 2.544(4) 2_566 ? C1 C2 1.376(8) . ? C1 H1A 0.9300 . ? C2 C3 1.372(9) . ? C2 H2A 0.9300 . ? C3 C4 1.379(8) . ? C3 H3A 0.9300 . ? C4 C5 1.405(7) . ? C4 H4A 0.9300 . ? C5 C6 1.472(7) . ? C6 C7 1.393(7) . ? C7 C8 1.371(8) . ? C7 H7A 0.9300 . ? C8 C9 1.391(7) . ? C8 C16 1.497(7) . ? C9 C10 1.391(7) . ? C9 H9A 0.9300 . ? C10 C11 1.495(7) . ? C11 C12 1.386(7) . ? C12 C13 1.380(8) . ? C12 H12A 0.9300 . ? C13 C14 1.384(9) . ? C13 H13A 0.9300 . ? C14 C15 1.380(8) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.401(7) . ? C16 C21 1.399(7) . ? C17 C18 1.386(7) . ? C18 C19 1.392(6) . ? C18 H18A 0.9300 . ? C19 C20 1.377(7) . ? C20 C21 1.391(7) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 C23 1.499(6) . ? C23 C24 1.381(7) . ? C23 C25 1.389(7) . ? C24 C25 1.383(7) 2_465 ? C24 H24A 0.9300 . ? O1W H1WA 0.8535 . ? O1W H1WB 0.8549 . ? O2W H2WA 0.8355 . ? O2W H2WB 0.8463 . ? C25 C24 1.383(7) 2_465 ? C25 H25A 0.9300 . ? 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 O7 Er1 O8 114.28(13) 2_565 . ? O7 Er1 O2 89.21(13) 2_565 . ? O8 Er1 O2 139.22(13) . . ? O7 Er1 O6 76.33(13) 2_565 2 ? O8 Er1 O6 75.60(14) . 2 ? O2 Er1 O6 78.68(13) . 2 ? O7 Er1 O5 77.96(13) 2_565 1_565 ? O8 Er1 O5 70.33(13) . 1_565 ? O2 Er1 O5 150.04(13) . 1_565 ? O6 Er1 O5 123.04(12) 2 1_565 ? O7 Er1 N2 139.97(14) 2_565 2_566 ? O8 Er1 N2 87.73(14) . 2_566 ? O2 Er1 N2 94.74(13) . 2_566 ? O6 Er1 N2 143.47(13) 2 2_566 ? O5 Er1 N2 79.09(13) 1_565 2_566 ? O7 Er1 N1 153.26(14) 2_565 2_566 ? O8 Er1 N1 69.99(13) . 2_566 ? O2 Er1 N1 74.67(13) . 2_566 ? O6 Er1 N1 79.62(13) 2 2_566 ? O5 Er1 N1 125.86(13) 1_565 2_566 ? N2 Er1 N1 64.08(13) 2_566 2_566 ? O7 Er1 N3 77.91(13) 2_565 2_566 ? O8 Er1 N3 134.36(14) . 2_566 ? O2 Er1 N3 81.02(13) . 2_566 ? O6 Er1 N3 147.20(14) 2 2_566 ? O5 Er1 N3 69.92(13) 1_565 2_566 ? N2 Er1 N3 63.53(14) 2_566 2_566 ? N1 Er1 N3 119.17(13) 2_566 2_566 ? O1 S1 O3 115.0(3) . . ? O1 S1 O2 112.6(2) . . ? O3 S1 O2 111.9(3) . . ? O1 S1 C17 104.8(2) . . ? O3 S1 C17 105.8(2) . . ? O2 S1 C17 105.8(2) . . ? O4 S2 O5 114.1(2) . . ? O4 S2 O6 112.9(2) . . ? O5 S2 O6 112.6(2) . . ? O4 S2 C19 106.3(2) . . ? O5 S2 C19 104.9(2) . . ? O6 S2 C19 105.2(2) . . ? S1 O2 Er1 139.3(2) . . ? S2 O5 Er1 159.8(2) . 1_545 ? S2 O6 Er1 137.7(2) . 2 ? C22 O7 Er1 148.0(3) . 2_565 ? C22 O8 Er1 150.8(3) . . ? C1 N1 C5 118.2(4) . . ? C1 N1 Er1 123.2(4) . 2_566 ? C5 N1 Er1 116.6(3) . 2_566 ? C10 N2 C6 118.1(4) . . ? C10 N2 Er1 120.2(3) . 2_566 ? C6 N2 Er1 119.2(3) . 2_566 ? C15 N3 C11 117.5(5) . . ? C15 N3 Er1 122.6(4) . 2_566 ? C11 N3 Er1 117.1(3) . 2_566 ? N1 C1 C2 124.0(6) . . ? N1 C1 H1A 118.0 . . ? C2 C1 H1A 118.0 . . ? C3 C2 C1 118.5(6) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? C2 C3 C4 119.3(5) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 119.2(5) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? N1 C5 C4 120.7(5) . . ? N1 C5 C6 116.0(4) . . ? C4 C5 C6 123.3(5) . . ? N2 C6 C7 122.0(5) . . ? N2 C6 C5 115.7(4) . . ? C7 C6 C5 122.2(5) . . ? C8 C7 C6 119.3(5) . . ? C8 C7 H7A 120.4 . . ? C6 C7 H7A 120.4 . . ? C7 C8 C9 119.5(5) . . ? C7 C8 C16 120.0(5) . . ? C9 C8 C16 120.4(5) . . ? C10 C9 C8 118.4(5) . . ? C10 C9 H9A 120.8 . . ? C8 C9 H9A 120.8 . . ? N2 C10 C9 122.5(5) . . ? N2 C10 C11 114.7(4) . . ? C9 C10 C11 122.8(5) . . ? N3 C11 C12 122.6(5) . . ? N3 C11 C10 115.3(4) . . ? C12 C11 C10 122.0(5) . . ? C13 C12 C11 118.8(6) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 119.0(6) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C13 C14 C15 118.3(5) . . ? C13 C14 H14A 120.8 . . ? C15 C14 H14A 120.8 . . ? N3 C15 C14 123.7(6) . . ? N3 C15 H15A 118.1 . . ? C14 C15 H15A 118.1 . . ? C17 C16 C21 116.9(5) . . ? C17 C16 C8 126.0(5) . . ? C21 C16 C8 116.9(5) . . ? C18 C17 C16 120.8(4) . . ? C18 C17 S1 113.7(4) . . ? C16 C17 S1 125.6(4) . . ? C17 C18 C19 120.5(4) . . ? C17 C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C20 C19 C18 120.0(5) . . ? C20 C19 S2 121.9(4) . . ? C18 C19 S2 118.0(4) . . ? C19 C20 C21 118.8(5) . . ? C19 C20 H20A 120.6 . . ? C21 C20 H20A 120.6 . . ? C20 C21 C16 122.6(5) . . ? C20 C21 H21A 118.7 . . ? C16 C21 H21A 118.7 . . ? O8 C22 O7 124.5(4) . . ? O8 C22 C23 118.2(4) . . ? O7 C22 C23 117.3(4) . . ? C24 C23 C25 119.8(4) . . ? C24 C23 C22 121.0(4) . . ? C25 C23 C22 119.2(4) . . ? C23 C24 C25 119.5(5) . 2_465 ? C23 C24 H24A 120.2 . . ? C25 C24 H24A 120.2 2_465 . ? H1WA O1W H1WB 106.4 . . ? H2WA O2W H2WB 109.1 . . ? C24 C25 C23 120.7(4) 2_465 . ? C24 C25 H25A 119.6 2_465 . ? C23 C25 H25A 119.6 . . ? 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 S1 O2 Er1 -44.1(4) . . . . ? O3 S1 O2 Er1 87.3(4) . . . . ? C17 S1 O2 Er1 -158.0(3) . . . . ? O7 Er1 O2 S1 8.7(4) 2_565 . . . ? O8 Er1 O2 S1 136.6(3) . . . . ? O6 Er1 O2 S1 85.0(4) 2 . . . ? O5 Er1 O2 S1 -55.1(5) 1_565 . . . ? N2 Er1 O2 S1 -131.4(4) 2_566 . . . ? N1 Er1 O2 S1 167.2(4) 2_566 . . . ? N3 Er1 O2 S1 -69.1(4) 2_566 . . . ? O4 S2 O5 Er1 -78.8(7) . . . 1_545 ? O6 S2 O5 Er1 51.6(7) . . . 1_545 ? C19 S2 O5 Er1 165.4(6) . . . 1_545 ? O4 S2 O6 Er1 115.2(3) . . . 2 ? O5 S2 O6 Er1 -15.7(4) . . . 2 ? C19 S2 O6 Er1 -129.3(3) . . . 2 ? O7 Er1 O8 C22 -19.2(8) 2_565 . . . ? O2 Er1 O8 C22 -139.2(7) . . . . ? O6 Er1 O8 C22 -86.6(8) 2 . . . ? O5 Er1 O8 C22 47.0(8) 1_565 . . . ? N2 Er1 O8 C22 126.2(8) 2_566 . . . ? N1 Er1 O8 C22 -170.6(8) 2_566 . . . ? N3 Er1 O8 C22 77.7(8) 2_566 . . . ? C5 N1 C1 C2 -1.6(8) . . . . ? Er1 N1 C1 C2 161.5(5) 2_566 . . . ? N1 C1 C2 C3 -0.6(9) . . . . ? C1 C2 C3 C4 2.4(9) . . . . ? C2 C3 C4 C5 -1.8(8) . . . . ? C1 N1 C5 C4 2.2(7) . . . . ? Er1 N1 C5 C4 -162.0(4) 2_566 . . . ? C1 N1 C5 C6 -176.7(5) . . . . ? Er1 N1 C5 C6 19.1(5) 2_566 . . . ? C3 C4 C5 N1 -0.5(8) . . . . ? C3 C4 C5 C6 178.3(5) . . . . ? C10 N2 C6 C7 -6.4(7) . . . . ? Er1 N2 C6 C7 155.7(4) 2_566 . . . ? C10 N2 C6 C5 172.2(4) . . . . ? Er1 N2 C6 C5 -25.7(5) 2_566 . . . ? N1 C5 C6 N2 3.4(6) . . . . ? C4 C5 C6 N2 -175.4(5) . . . . ? N1 C5 C6 C7 -178.0(4) . . . . ? C4 C5 C6 C7 3.2(8) . . . . ? N2 C6 C7 C8 3.4(8) . . . . ? C5 C6 C7 C8 -175.1(5) . . . . ? C6 C7 C8 C9 1.3(7) . . . . ? C6 C7 C8 C16 -175.7(4) . . . . ? C7 C8 C9 C10 -2.8(7) . . . . ? C16 C8 C9 C10 174.2(4) . . . . ? C6 N2 C10 C9 4.8(7) . . . . ? Er1 N2 C10 C9 -157.1(4) 2_566 . . . ? C6 N2 C10 C11 -175.0(4) . . . . ? Er1 N2 C10 C11 23.2(5) 2_566 . . . ? C8 C9 C10 N2 -0.3(7) . . . . ? C8 C9 C10 C11 179.4(4) . . . . ? C15 N3 C11 C12 -2.0(7) . . . . ? Er1 N3 C11 C12 159.4(4) 2_566 . . . ? C15 N3 C11 C10 174.6(4) . . . . ? Er1 N3 C11 C10 -24.0(5) 2_566 . . . ? N2 C10 C11 N3 1.5(6) . . . . ? C9 C10 C11 N3 -178.2(4) . . . . ? N2 C10 C11 C12 178.2(5) . . . . ? C9 C10 C11 C12 -1.6(8) . . . . ? N3 C11 C12 C13 0.9(8) . . . . ? C10 C11 C12 C13 -175.5(5) . . . . ? C11 C12 C13 C14 1.9(9) . . . . ? C12 C13 C14 C15 -3.3(9) . . . . ? C11 N3 C15 C14 0.4(8) . . . . ? Er1 N3 C15 C14 -159.9(4) 2_566 . . . ? C13 C14 C15 N3 2.3(9) . . . . ? C7 C8 C16 C17 -41.7(8) . . . . ? C9 C8 C16 C17 141.3(5) . . . . ? C7 C8 C16 C21 133.7(5) . . . . ? C9 C8 C16 C21 -43.3(7) . . . . ? C21 C16 C17 C18 -4.4(8) . . . . ? C8 C16 C17 C18 171.1(5) . . . . ? C21 C16 C17 S1 177.1(4) . . . . ? C8 C16 C17 S1 -7.4(8) . . . . ? O1 S1 C17 C18 26.7(5) . . . . ? O3 S1 C17 C18 -95.2(4) . . . . ? O2 S1 C17 C18 145.9(4) . . . . ? O1 S1 C17 C16 -154.7(5) . . . . ? O3 S1 C17 C16 83.4(5) . . . . ? O2 S1 C17 C16 -35.5(5) . . . . ? C16 C17 C18 C19 -0.3(8) . . . . ? S1 C17 C18 C19 178.4(4) . . . . ? C17 C18 C19 C20 4.7(8) . . . . ? C17 C18 C19 S2 -172.2(4) . . . . ? O4 S2 C19 C20 -124.8(5) . . . . ? O5 S2 C19 C20 -3.7(5) . . . . ? O6 S2 C19 C20 115.2(5) . . . . ? O4 S2 C19 C18 52.1(5) . . . . ? O5 S2 C19 C18 173.2(4) . . . . ? O6 S2 C19 C18 -67.9(4) . . . . ? C18 C19 C20 C21 -4.1(8) . . . . ? S2 C19 C20 C21 172.7(4) . . . . ? C19 C20 C21 C16 -0.9(9) . . . . ? C17 C16 C21 C20 5.0(8) . . . . ? C8 C16 C21 C20 -170.8(5) . . . . ? Er1 O8 C22 O7 8.5(11) . . . . ? Er1 O8 C22 C23 -171.9(5) . . . . ? Er1 O7 C22 O8 16.9(10) 2_565 . . . ? Er1 O7 C22 C23 -162.7(4) 2_565 . . . ? O8 C22 C23 C24 157.6(5) . . . . ? O7 C22 C23 C24 -22.8(7) . . . . ? O8 C22 C23 C25 -21.8(8) . . . . ? O7 C22 C23 C25 157.8(5) . . . . ? C25 C23 C24 C25 -0.9(10) . . . 2_465 ? C22 C23 C24 C25 179.7(5) . . . 2_465 ? C24 C23 C25 C24 0.9(10) . . . 2_465 ? C22 C23 C25 C24 -179.7(5) . . . 2_465 ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.844 _refine_diff_density_min -0.921 _refine_diff_density_rms 0.143 ############################################################################ _database_code_depnum_ccdc_archive 'CCDC 946698'