# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_121117a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 Eu2 N8 O15 S2' _chemical_formula_weight 1232.78 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' 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' 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 6.9016(6) _cell_length_b 10.1652(9) _cell_length_c 15.2500(13) _cell_angle_alpha 83.715(2) _cell_angle_beta 78.047(2) _cell_angle_gamma 77.496(2) _cell_volume 1019.52(15) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1130 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 23.37 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.008 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 3.236 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7379 _exptl_absorpt_correction_T_max 0.9381 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5233 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0774 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.24 _reflns_number_total 3646 _reflns_number_gt 3117 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0496P)^2^+0.2384P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3646 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1874(9) 0.6842(7) -0.1592(5) 0.0170(15) Uani 1 1 d . . . C2 C 0.2108(12) 0.5823(7) -0.2158(5) 0.0272(18) Uani 1 1 d . . . H2 H 0.1976 0.6033 -0.2754 0.033 Uiso 1 1 calc R . . C3 C 0.2538(12) 0.4488(8) -0.1831(5) 0.0297(18) Uani 1 1 d . . . H3 H 0.2649 0.3799 -0.2204 0.036 Uiso 1 1 calc R . . C4 C 0.2805(10) 0.4172(7) -0.0943(5) 0.0206(16) Uani 1 1 d . . . C5 C 0.2529(12) 0.5205(8) -0.0395(5) 0.0282(18) Uani 1 1 d . . . H5 H 0.2669 0.5008 0.0201 0.034 Uiso 1 1 calc R . . C6 C 0.2044(12) 0.6541(7) -0.0719(5) 0.0271(18) Uani 1 1 d . . . H6 H 0.1835 0.7231 -0.0336 0.033 Uiso 1 1 calc R . . C7 C 0.3349(11) 0.2705(8) -0.0598(5) 0.0271(17) Uani 1 1 d . . . C8 C 0.3779(12) -0.1654(8) 0.3056(5) 0.0296(18) Uani 1 1 d . . . H8 H 0.4064 -0.2237 0.2596 0.036 Uiso 1 1 calc R . . C9 C 0.3481(12) -0.2213(8) 0.3951(5) 0.0298(18) Uani 1 1 d . . . H9 H 0.3635 -0.3141 0.4080 0.036 Uiso 1 1 calc R . . C10 C 0.2958(12) -0.1342(8) 0.4618(5) 0.0285(18) Uani 1 1 d . . . H10 H 0.2691 -0.1671 0.5215 0.034 Uiso 1 1 calc R . . C11 C 0.2822(11) 0.0042(7) 0.4409(5) 0.0248(17) Uani 1 1 d . . . C12 C 0.2255(11) 0.1062(8) 0.5039(5) 0.0265(17) Uani 1 1 d . . . C13 C 0.1369(12) 0.2206(9) 0.6224(5) 0.035(2) Uani 1 1 d . . . H13 H 0.0999 0.2405 0.6824 0.042 Uiso 1 1 calc R . . C14 C 0.2062(11) 0.2406(8) 0.4808(5) 0.0256(17) Uani 1 1 d . . . C15 C 0.2394(10) 0.2897(8) 0.3883(5) 0.0229(16) Uani 1 1 d . . . C16 C 0.2125(12) 0.4280(8) 0.3604(5) 0.0326(19) Uani 1 1 d . . . H16 H 0.1714 0.4929 0.4025 0.039 Uiso 1 1 calc R . . C17 C 0.2479(12) 0.4658(7) 0.2701(5) 0.0302(19) Uani 1 1 d . . . H17 H 0.2325 0.5564 0.2497 0.036 Uiso 1 1 calc R . . C18 C 0.3076(11) 0.3642(7) 0.2100(5) 0.0233(16) Uani 1 1 d . . . H18 H 0.3308 0.3905 0.1490 0.028 Uiso 1 1 calc R . . C19 C 0.2983(10) 0.1958(7) 0.3230(5) 0.0181(15) Uani 1 1 d . . . C20 C 0.3180(10) 0.0517(7) 0.3487(4) 0.0187(15) Uani 1 1 d . . . N1 N 0.3679(9) -0.0355(6) 0.2832(4) 0.0233(14) Uani 1 1 d . . . N2 N 0.3335(8) 0.2339(6) 0.2331(4) 0.0188(13) Uani 1 1 d . . . N3 N 0.1491(10) 0.3148(7) 0.5561(4) 0.0329(16) Uani 1 1 d . . . N4 N 0.1816(10) 0.0954(7) 0.5970(4) 0.0317(16) Uani 1 1 d . . . H4 H 0.1830 0.0223 0.6313 0.038 Uiso 1 1 calc R . . O1 O 0.2591(7) 0.9257(5) -0.1672(4) 0.0304(13) Uani 1 1 d . . . O2 O 0.1647(9) 0.8561(5) -0.2962(3) 0.0357(14) Uani 1 1 d . . . O3 O -0.0784(7) 0.9066(5) -0.1605(4) 0.0295(12) Uani 1 1 d . . . O4 O 0.3726(8) 0.1825(5) -0.1143(3) 0.0315(13) Uani 1 1 d . . . O5 O 0.3415(8) 0.2509(5) 0.0236(3) 0.0282(12) Uani 1 1 d . . . O6 O 0.3140(7) -0.0483(5) 0.0175(3) 0.0235(11) Uani 1 1 d . . . H6A H 0.2972 -0.0556 -0.0355 0.035 Uiso 1 1 d R . . O1W O 0.9073(13) 0.2291(7) 0.8540(5) 0.072(2) Uani 1 1 d . . . H1WA H 1.0284 0.2167 0.8626 0.108 Uiso 1 1 d R . . H1WB H 0.8587 0.1581 0.8689 0.108 Uiso 1 1 d R . . O2W O 0.694(2) 0.4495(12) 0.4398(7) 0.051(4) Uani 0.50 1 d P . . H2WA H 0.7447 0.5197 0.4340 0.077 Uiso 0.50 1 d PR . . H2WB H 0.5806 0.4771 0.4742 0.077 Uiso 0.50 1 d PR . . S1 S 0.1291(2) 0.85491(17) -0.19995(11) 0.0169(4) Uani 1 1 d . . . Eu1 Eu 0.44344(5) 0.05227(4) 0.11483(2) 0.01779(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.009(3) 0.020(4) 0.024(4) 0.000(3) -0.005(3) -0.007(3) C2 0.041(5) 0.021(4) 0.019(4) -0.002(3) -0.014(3) 0.001(4) C3 0.051(5) 0.015(4) 0.024(4) 0.001(3) -0.013(4) -0.005(4) C4 0.023(4) 0.009(3) 0.027(4) 0.000(3) -0.001(3) -0.001(3) C5 0.037(5) 0.033(5) 0.016(4) -0.001(3) -0.007(3) -0.007(4) C6 0.045(5) 0.013(4) 0.024(4) -0.006(3) -0.006(3) -0.004(3) C7 0.031(4) 0.022(4) 0.025(4) -0.003(3) -0.006(3) 0.002(3) C8 0.035(5) 0.018(4) 0.036(5) 0.001(4) -0.008(4) -0.007(4) C9 0.035(5) 0.016(4) 0.038(5) 0.011(4) -0.008(4) -0.011(4) C10 0.036(5) 0.019(4) 0.027(4) 0.006(3) -0.004(3) -0.006(3) C11 0.029(4) 0.017(4) 0.027(4) 0.000(3) -0.007(3) -0.001(3) C12 0.032(4) 0.025(4) 0.021(4) 0.003(3) -0.006(3) -0.005(3) C13 0.042(5) 0.041(5) 0.020(4) -0.007(4) -0.001(4) -0.009(4) C14 0.027(4) 0.027(4) 0.022(4) -0.004(3) -0.002(3) -0.006(3) C15 0.020(4) 0.032(4) 0.018(4) -0.005(3) -0.003(3) -0.007(3) C16 0.043(5) 0.024(4) 0.029(4) -0.005(4) -0.010(4) 0.000(4) C17 0.049(5) 0.010(4) 0.025(4) -0.002(3) -0.003(4) 0.005(4) C18 0.026(4) 0.024(4) 0.020(4) 0.001(3) -0.007(3) -0.004(3) C19 0.016(3) 0.016(4) 0.025(4) -0.003(3) -0.002(3) -0.009(3) C20 0.021(4) 0.011(4) 0.020(4) 0.001(3) -0.005(3) 0.004(3) N1 0.033(4) 0.012(3) 0.023(3) -0.001(3) -0.004(3) -0.001(3) N2 0.019(3) 0.018(3) 0.019(3) 0.005(3) -0.004(2) -0.005(3) N3 0.042(4) 0.030(4) 0.024(3) -0.004(3) -0.001(3) -0.006(3) N4 0.042(4) 0.027(4) 0.023(3) 0.008(3) -0.005(3) -0.008(3) O1 0.024(3) 0.024(3) 0.051(3) -0.002(3) -0.018(3) -0.010(2) O2 0.063(4) 0.024(3) 0.017(3) 0.008(2) -0.002(3) -0.011(3) O3 0.021(3) 0.019(3) 0.045(3) 0.002(3) -0.004(2) 0.000(2) O4 0.048(3) 0.015(3) 0.030(3) -0.005(2) -0.011(3) 0.001(3) O5 0.046(3) 0.014(3) 0.022(3) -0.002(2) -0.008(2) 0.002(2) O6 0.027(3) 0.024(3) 0.021(3) -0.003(2) -0.005(2) -0.006(2) O1W 0.114(7) 0.047(4) 0.063(5) 0.007(4) -0.029(5) -0.026(5) O2W 0.097(11) 0.031(7) 0.025(6) 0.002(5) 0.000(6) -0.023(7) S1 0.0191(9) 0.0119(9) 0.0196(9) 0.0005(7) -0.0047(7) -0.0029(7) Eu1 0.0207(2) 0.0135(2) 0.0185(2) -0.00028(14) -0.00463(14) -0.00150(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.357(10) . ? C1 C2 1.382(10) . ? C1 S1 1.767(7) . ? C2 C3 1.384(10) . ? C2 H2 0.9300 . ? C3 C4 1.397(10) . ? C3 H3 0.9300 . ? C4 C5 1.370(10) . ? C4 C7 1.520(10) . ? C5 C6 1.388(10) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O4 1.238(9) . ? C7 O5 1.275(9) . ? C8 N1 1.318(9) . ? C8 C9 1.411(11) . ? C8 H8 0.9300 . ? C9 C10 1.363(11) . ? C9 H9 0.9300 . ? C10 C11 1.396(10) . ? C10 H10 0.9300 . ? C11 C20 1.424(10) . ? C11 C12 1.428(10) . ? C12 C14 1.357(10) . ? C12 N4 1.387(9) . ? C13 N3 1.318(10) . ? C13 N4 1.324(10) . ? C13 H13 0.9300 . ? C14 N3 1.384(9) . ? C14 C15 1.433(10) . ? C15 C19 1.392(10) . ? C15 C16 1.407(11) . ? C16 C17 1.374(10) . ? C16 H16 0.9300 . ? C17 C18 1.394(10) . ? C17 H17 0.9300 . ? C18 N2 1.316(9) . ? C18 H18 0.9300 . ? C19 N2 1.370(9) . ? C19 C20 1.459(9) . ? C20 N1 1.349(9) . ? N1 Eu1 2.609(6) . ? N2 Eu1 2.606(6) . ? N4 H4 0.8600 . ? O1 S1 1.455(5) . ? O1 Eu1 2.413(5) 2_665 ? O2 S1 1.436(5) . ? O3 S1 1.441(5) . ? O3 Eu1 2.426(5) 2_565 ? O4 Eu1 2.449(5) 2_655 ? O5 Eu1 2.384(5) . ? O6 Eu1 2.307(5) . ? O6 Eu1 2.338(5) 2_655 ? O6 H6A 0.8529 . ? O1W H1WA 0.8534 . ? O1W H1WB 0.8503 . ? O2W H2WA 0.8505 . ? O2W H2WB 0.8546 . ? Eu1 O6 2.338(5) 2_655 ? Eu1 O1 2.413(5) 2_665 ? Eu1 O3 2.426(5) 2_565 ? Eu1 O4 2.449(5) 2_655 ? Eu1 Eu1 3.6510(7) 2_655 ? 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 C6 C1 C2 120.4(7) . . ? C6 C1 S1 119.7(5) . . ? C2 C1 S1 119.9(5) . . ? C1 C2 C3 119.6(7) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 120.2(7) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 118.7(7) . . ? C5 C4 C7 121.3(6) . . ? C3 C4 C7 120.0(6) . . ? C4 C5 C6 120.8(7) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 120.2(7) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? O4 C7 O5 126.3(7) . . ? O4 C7 C4 118.1(6) . . ? O5 C7 C4 115.6(6) . . ? N1 C8 C9 123.9(7) . . ? N1 C8 H8 118.0 . . ? C9 C8 H8 118.0 . . ? C10 C9 C8 117.5(7) . . ? C10 C9 H9 121.2 . . ? C8 C9 H9 121.2 . . ? C9 C10 C11 120.2(7) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C20 118.5(7) . . ? C10 C11 C12 125.9(7) . . ? C20 C11 C12 115.6(6) . . ? C14 C12 N4 105.3(7) . . ? C14 C12 C11 124.2(7) . . ? N4 C12 C11 130.5(7) . . ? N3 C13 N4 114.8(7) . . ? N3 C13 H13 122.6 . . ? N4 C13 H13 122.6 . . ? C12 C14 N3 111.2(6) . . ? C12 C14 C15 120.7(7) . . ? N3 C14 C15 128.0(7) . . ? C19 C15 C16 118.6(6) . . ? C19 C15 C14 118.2(7) . . ? C16 C15 C14 123.2(7) . . ? C17 C16 C15 119.1(7) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 118.0(7) . . ? C16 C17 H17 121.0 . . ? C18 C17 H17 121.0 . . ? N2 C18 C17 124.9(7) . . ? N2 C18 H18 117.5 . . ? C17 C18 H18 117.5 . . ? N2 C19 C15 122.1(6) . . ? N2 C19 C20 117.4(6) . . ? C15 C19 C20 120.5(6) . . ? N1 C20 C11 120.7(6) . . ? N1 C20 C19 118.5(6) . . ? C11 C20 C19 120.7(6) . . ? C8 N1 C20 119.1(6) . . ? C8 N1 Eu1 120.5(5) . . ? C20 N1 Eu1 120.4(4) . . ? C18 N2 C19 117.3(6) . . ? C18 N2 Eu1 122.4(4) . . ? C19 N2 Eu1 120.4(4) . . ? C13 N3 C14 102.7(7) . . ? C13 N4 C12 105.9(7) . . ? C13 N4 H4 127.0 . . ? C12 N4 H4 127.0 . . ? S1 O1 Eu1 155.8(3) . 2_665 ? S1 O3 Eu1 165.0(3) . 2_565 ? C7 O4 Eu1 133.6(5) . 2_655 ? C7 O5 Eu1 132.2(5) . . ? Eu1 O6 Eu1 103.62(18) . 2_655 ? Eu1 O6 H6A 150.1 . . ? Eu1 O6 H6A 52.9 2_655 . ? H1WA O1W H1WB 111.4 . . ? H2WA O2W H2WB 100.2 . . ? O2 S1 O3 113.4(3) . . ? O2 S1 O1 113.3(3) . . ? O3 S1 O1 109.1(3) . . ? O2 S1 C1 106.9(3) . . ? O3 S1 C1 107.0(3) . . ? O1 S1 C1 106.8(3) . . ? O6 Eu1 O6 76.38(18) . 2_655 ? O6 Eu1 O5 82.75(17) . . ? O6 Eu1 O5 72.70(17) 2_655 . ? O6 Eu1 O1 146.67(18) . 2_665 ? O6 Eu1 O1 77.26(17) 2_655 2_665 ? O5 Eu1 O1 108.30(18) . 2_665 ? O6 Eu1 O3 71.60(17) . 2_565 ? O6 Eu1 O3 138.77(17) 2_655 2_565 ? O5 Eu1 O3 78.06(17) . 2_565 ? O1 Eu1 O3 140.64(18) 2_665 2_565 ? O6 Eu1 O4 74.62(17) . 2_655 ? O6 Eu1 O4 76.31(17) 2_655 2_655 ? O5 Eu1 O4 145.08(17) . 2_655 ? O1 Eu1 O4 79.62(18) 2_665 2_655 ? O3 Eu1 O4 117.88(18) 2_565 2_655 ? O6 Eu1 N2 141.07(17) . . ? O6 Eu1 N2 128.36(17) 2_655 . ? O5 Eu1 N2 78.72(16) . . ? O1 Eu1 N2 72.16(18) 2_665 . ? O3 Eu1 N2 71.23(17) 2_565 . ? O4 Eu1 N2 134.62(17) 2_655 . ? O6 Eu1 N1 115.63(18) . . ? O6 Eu1 N1 145.78(18) 2_655 . ? O5 Eu1 N1 137.96(17) . . ? O1 Eu1 N1 77.60(19) 2_665 . ? O3 Eu1 N1 73.46(18) 2_565 . ? O4 Eu1 N1 76.63(17) 2_655 . ? N2 Eu1 N1 63.24(17) . . ? O6 Eu1 Eu1 38.50(12) . 2_655 ? O6 Eu1 Eu1 37.89(12) 2_655 2_655 ? O5 Eu1 Eu1 74.32(12) . 2_655 ? O1 Eu1 Eu1 112.75(13) 2_665 2_655 ? O3 Eu1 Eu1 106.39(13) 2_565 2_655 ? O4 Eu1 Eu1 71.39(12) 2_655 2_655 ? N2 Eu1 Eu1 152.75(12) . 2_655 ? N1 Eu1 Eu1 143.41(13) . 2_655 ? 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 C6 C1 C2 C3 -0.7(11) . . . . ? S1 C1 C2 C3 -179.1(6) . . . . ? C1 C2 C3 C4 -2.2(12) . . . . ? C2 C3 C4 C5 3.3(12) . . . . ? C2 C3 C4 C7 -177.9(7) . . . . ? C3 C4 C5 C6 -1.6(11) . . . . ? C7 C4 C5 C6 179.6(7) . . . . ? C2 C1 C6 C5 2.4(11) . . . . ? S1 C1 C6 C5 -179.1(6) . . . . ? C4 C5 C6 C1 -1.3(12) . . . . ? C5 C4 C7 O4 -174.6(7) . . . . ? C3 C4 C7 O4 6.6(11) . . . . ? C5 C4 C7 O5 3.8(11) . . . . ? C3 C4 C7 O5 -175.0(7) . . . . ? N1 C8 C9 C10 3.4(12) . . . . ? C8 C9 C10 C11 -2.8(12) . . . . ? C9 C10 C11 C20 1.9(11) . . . . ? C9 C10 C11 C12 178.7(7) . . . . ? C10 C11 C12 C14 -177.3(8) . . . . ? C20 C11 C12 C14 -0.4(11) . . . . ? C10 C11 C12 N4 3.5(14) . . . . ? C20 C11 C12 N4 -179.6(8) . . . . ? N4 C12 C14 N3 -0.8(9) . . . . ? C11 C12 C14 N3 179.9(7) . . . . ? N4 C12 C14 C15 -179.5(7) . . . . ? C11 C12 C14 C15 1.2(12) . . . . ? C12 C14 C15 C19 -2.1(11) . . . . ? N3 C14 C15 C19 179.5(7) . . . . ? C12 C14 C15 C16 177.0(8) . . . . ? N3 C14 C15 C16 -1.5(13) . . . . ? C19 C15 C16 C17 -0.9(11) . . . . ? C14 C15 C16 C17 -180.0(7) . . . . ? C15 C16 C17 C18 0.6(12) . . . . ? C16 C17 C18 N2 -0.2(12) . . . . ? C16 C15 C19 N2 1.0(10) . . . . ? C14 C15 C19 N2 -179.9(6) . . . . ? C16 C15 C19 C20 -176.9(7) . . . . ? C14 C15 C19 C20 2.2(10) . . . . ? C10 C11 C20 N1 -1.3(11) . . . . ? C12 C11 C20 N1 -178.5(7) . . . . ? C10 C11 C20 C19 177.7(7) . . . . ? C12 C11 C20 C19 0.5(10) . . . . ? N2 C19 C20 N1 -0.4(10) . . . . ? C15 C19 C20 N1 177.5(6) . . . . ? N2 C19 C20 C11 -179.5(6) . . . . ? C15 C19 C20 C11 -1.5(10) . . . . ? C9 C8 N1 C20 -2.9(12) . . . . ? C9 C8 N1 Eu1 177.1(6) . . . . ? C11 C20 N1 C8 1.8(11) . . . . ? C19 C20 N1 C8 -177.2(7) . . . . ? C11 C20 N1 Eu1 -178.2(5) . . . . ? C19 C20 N1 Eu1 2.8(8) . . . . ? C17 C18 N2 C19 0.2(11) . . . . ? C17 C18 N2 Eu1 179.6(6) . . . . ? C15 C19 N2 C18 -0.6(10) . . . . ? C20 C19 N2 C18 177.3(6) . . . . ? C15 C19 N2 Eu1 180.0(5) . . . . ? C20 C19 N2 Eu1 -2.1(8) . . . . ? N4 C13 N3 C14 0.5(10) . . . . ? C12 C14 N3 C13 0.2(9) . . . . ? C15 C14 N3 C13 178.8(8) . . . . ? N3 C13 N4 C12 -1.0(10) . . . . ? C14 C12 N4 C13 1.0(9) . . . . ? C11 C12 N4 C13 -179.7(8) . . . . ? O5 C7 O4 Eu1 -19.1(12) . . . 2_655 ? C4 C7 O4 Eu1 159.1(5) . . . 2_655 ? O4 C7 O5 Eu1 4.5(12) . . . . ? C4 C7 O5 Eu1 -173.7(4) . . . . ? Eu1 O3 S1 O2 56.8(13) 2_565 . . . ? Eu1 O3 S1 O1 -175.9(12) 2_565 . . . ? Eu1 O3 S1 C1 -60.8(13) 2_565 . . . ? Eu1 O1 S1 O2 -90.8(9) 2_665 . . . ? Eu1 O1 S1 O3 141.8(8) 2_665 . . . ? Eu1 O1 S1 C1 26.5(9) 2_665 . . . ? C6 C1 S1 O2 167.6(6) . . . . ? C2 C1 S1 O2 -13.9(7) . . . . ? C6 C1 S1 O3 -70.6(6) . . . . ? C2 C1 S1 O3 107.9(6) . . . . ? C6 C1 S1 O1 46.1(7) . . . . ? C2 C1 S1 O1 -135.4(6) . . . . ? Eu1 O6 Eu1 O6 0.0 2_655 . . 2_655 ? Eu1 O6 Eu1 O5 73.88(19) 2_655 . . . ? Eu1 O6 Eu1 O1 -38.6(4) 2_655 . . 2_665 ? Eu1 O6 Eu1 O3 153.7(2) 2_655 . . 2_565 ? Eu1 O6 Eu1 O4 -79.3(2) 2_655 . . 2_655 ? Eu1 O6 Eu1 N2 135.8(2) 2_655 . . . ? Eu1 O6 Eu1 N1 -145.84(18) 2_655 . . . ? C7 O5 Eu1 O6 -33.3(7) . . . . ? C7 O5 Eu1 O6 44.6(7) . . . 2_655 ? C7 O5 Eu1 O1 114.4(7) . . . 2_665 ? C7 O5 Eu1 O3 -105.9(7) . . . 2_565 ? C7 O5 Eu1 O4 16.2(8) . . . 2_655 ? C7 O5 Eu1 N2 -178.9(7) . . . . ? C7 O5 Eu1 N1 -154.0(6) . . . . ? C7 O5 Eu1 Eu1 5.1(6) . . . 2_655 ? C18 N2 Eu1 O6 -78.5(6) . . . . ? C19 N2 Eu1 O6 100.8(5) . . . . ? C18 N2 Eu1 O6 41.6(6) . . . 2_655 ? C19 N2 Eu1 O6 -139.0(4) . . . 2_655 ? C18 N2 Eu1 O5 -15.4(5) . . . . ? C19 N2 Eu1 O5 164.0(5) . . . . ? C18 N2 Eu1 O1 98.2(5) . . . 2_665 ? C19 N2 Eu1 O1 -82.4(5) . . . 2_665 ? C18 N2 Eu1 O3 -96.5(5) . . . 2_565 ? C19 N2 Eu1 O3 82.9(5) . . . 2_565 ? C18 N2 Eu1 O4 152.5(5) . . . 2_655 ? C19 N2 Eu1 O4 -28.1(6) . . . 2_655 ? C18 N2 Eu1 N1 -176.9(6) . . . . ? C19 N2 Eu1 N1 2.4(5) . . . . ? C18 N2 Eu1 Eu1 -7.0(7) . . . 2_655 ? C19 N2 Eu1 Eu1 172.4(3) . . . 2_655 ? C8 N1 Eu1 O6 40.9(6) . . . . ? C20 N1 Eu1 O6 -139.1(5) . . . . ? C8 N1 Eu1 O6 -63.0(7) . . . 2_655 ? C20 N1 Eu1 O6 117.0(5) . . . 2_655 ? C8 N1 Eu1 O5 149.8(5) . . . . ? C20 N1 Eu1 O5 -30.2(7) . . . . ? C8 N1 Eu1 O1 -106.6(6) . . . 2_665 ? C20 N1 Eu1 O1 73.4(5) . . . 2_665 ? C8 N1 Eu1 O3 100.4(6) . . . 2_565 ? C20 N1 Eu1 O3 -79.6(5) . . . 2_565 ? C8 N1 Eu1 O4 -24.5(6) . . . 2_655 ? C20 N1 Eu1 O4 155.5(6) . . . 2_655 ? C8 N1 Eu1 N2 177.3(6) . . . . ? C20 N1 Eu1 N2 -2.6(5) . . . . ? C8 N1 Eu1 Eu1 5.0(7) . . . 2_655 ? C20 N1 Eu1 Eu1 -175.0(4) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.798 _refine_diff_density_min -0.692 _refine_diff_density_rms 0.173 _database_code_depnum_ccdc_archive 'CCDC 956197' ####################################################################### # # 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_130519b_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 Gd2 N8 O15 S2' _chemical_formula_weight 1243.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8982(4) _cell_length_b 10.1549(6) _cell_length_c 15.2233(8) _cell_angle_alpha 83.8120(10) _cell_angle_beta 78.1380(10) _cell_angle_gamma 77.5150(10) _cell_volume 1016.71(10) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3622 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 27.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 3.422 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7260 _exptl_absorpt_correction_T_max 0.9347 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5112 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3631 _reflns_number_gt 3383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0496P)^2^+0.2384P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3631 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0252 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0653 _refine_ls_wR_factor_gt 0.0639 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.916 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1855(5) 0.6837(4) -0.1584(3) 0.0200(8) Uani 1 1 d . . . C2 C 0.2079(6) 0.5816(4) -0.2151(3) 0.0255(8) Uani 1 1 d . . . H2 H 0.1917 0.6024 -0.2745 0.031 Uiso 1 1 calc R . . C3 C 0.2549(6) 0.4482(4) -0.1824(3) 0.0266(9) Uani 1 1 d . . . H3 H 0.2711 0.3790 -0.2203 0.032 Uiso 1 1 calc R . . C4 C 0.2778(6) 0.4170(4) -0.0935(3) 0.0232(8) Uani 1 1 d . . . C5 C 0.2507(7) 0.5215(4) -0.0381(3) 0.0303(9) Uani 1 1 d . . . H5 H 0.2637 0.5016 0.0218 0.036 Uiso 1 1 calc R . . C6 C 0.2048(7) 0.6542(4) -0.0702(3) 0.0291(9) Uani 1 1 d . . . H6 H 0.1871 0.7236 -0.0323 0.035 Uiso 1 1 calc R . . C7 C 0.3357(6) 0.2709(4) -0.0590(3) 0.0217(8) Uani 1 1 d . . . C8 C 0.3802(6) -0.1671(4) 0.3051(3) 0.0288(9) Uani 1 1 d . . . H8 H 0.4098 -0.2265 0.2596 0.035 Uiso 1 1 calc R . . C9 C 0.3486(7) -0.2208(4) 0.3945(3) 0.0349(10) Uani 1 1 d . . . H9 H 0.3607 -0.3134 0.4076 0.042 Uiso 1 1 calc R . . C10 C 0.3000(6) -0.1348(4) 0.4614(3) 0.0302(9) Uani 1 1 d . . . H10 H 0.2792 -0.1681 0.5212 0.036 Uiso 1 1 calc R . . C11 C 0.2813(5) 0.0042(4) 0.4400(3) 0.0220(8) Uani 1 1 d . . . C12 C 0.2259(6) 0.1061(4) 0.5035(3) 0.0264(9) Uani 1 1 d . . . C13 C 0.1358(7) 0.2204(5) 0.6237(3) 0.0376(10) Uani 1 1 d . . . H13 H 0.0986 0.2399 0.6838 0.045 Uiso 1 1 calc R . . C14 C 0.2051(6) 0.2408(4) 0.4812(3) 0.0253(8) Uani 1 1 d . . . C15 C 0.2400(6) 0.2918(4) 0.3879(3) 0.0232(8) Uani 1 1 d . . . C16 C 0.2154(6) 0.4283(4) 0.3598(3) 0.0291(9) Uani 1 1 d . . . H16 H 0.1761 0.4937 0.4018 0.035 Uiso 1 1 calc R . . C17 C 0.2498(6) 0.4655(4) 0.2696(3) 0.0297(9) Uani 1 1 d . . . H17 H 0.2331 0.5563 0.2493 0.036 Uiso 1 1 calc R . . C18 C 0.3100(6) 0.3652(4) 0.2093(3) 0.0257(8) Uani 1 1 d . . . H18 H 0.3340 0.3915 0.1482 0.031 Uiso 1 1 calc R . . C19 C 0.2998(5) 0.1951(4) 0.3222(2) 0.0192(8) Uani 1 1 d . . . C20 C 0.3179(5) 0.0516(4) 0.3479(2) 0.0199(8) Uani 1 1 d . . . N1 N 0.3705(5) -0.0367(3) 0.2817(2) 0.0230(7) Uani 1 1 d . . . N2 N 0.3356(4) 0.2338(3) 0.2328(2) 0.0189(6) Uani 1 1 d . . . N3 N 0.1497(6) 0.3151(4) 0.5565(2) 0.0370(9) Uani 1 1 d . . . N4 N 0.1803(5) 0.0940(4) 0.5965(2) 0.0306(8) Uani 1 1 d . . . H4 H 0.1806 0.0204 0.6302 0.037 Uiso 1 1 calc R . . O1 O 0.2575(4) 0.9262(3) -0.1665(2) 0.0306(6) Uani 1 1 d . . . O2 O 0.1646(5) 0.8561(3) -0.29649(19) 0.0381(8) Uani 1 1 d . . . O3 O -0.0801(4) 0.9068(3) -0.1604(2) 0.0299(6) Uani 1 1 d . . . O4 O 0.3751(4) 0.1806(3) -0.11419(18) 0.0280(6) Uani 1 1 d . . . O5 O 0.3395(4) 0.2491(3) 0.02405(18) 0.0272(6) Uani 1 1 d . . . O6 O 0.3123(4) -0.0494(3) 0.01766(17) 0.0228(6) Uani 1 1 d . . . H6A H 0.2955 -0.0568 -0.0353 0.034 Uiso 1 1 d R . . O1W O 0.9087(7) 0.2293(4) 0.8537(3) 0.0688(12) Uani 1 1 d . . . H1WA H 1.0298 0.2169 0.8623 0.103 Uiso 1 1 d R . . H1WB H 0.8600 0.1583 0.8686 0.103 Uiso 1 1 d R . . O2W O 0.6938(13) 0.4499(7) 0.4402(5) 0.059(2) Uani 0.50 1 d P . . H2WA H 0.7450 0.5200 0.4345 0.089 Uiso 0.50 1 d PR . . H2WB H 0.5809 0.4775 0.4747 0.089 Uiso 0.50 1 d PR . . S1 S 0.12856(13) 0.85478(8) -0.19961(6) 0.01679(19) Uani 1 1 d . . . Gd1 Gd 0.44409(2) 0.052210(16) 0.114443(11) 0.01640(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0210(18) 0.0145(18) 0.024(2) 0.0022(15) -0.0038(15) -0.0041(14) C2 0.037(2) 0.0180(19) 0.022(2) 0.0000(16) -0.0134(17) -0.0004(17) C3 0.040(2) 0.0168(19) 0.023(2) -0.0033(16) -0.0101(17) -0.0013(17) C4 0.0258(19) 0.0171(18) 0.025(2) 0.0015(15) -0.0030(15) -0.0038(15) C5 0.053(3) 0.022(2) 0.0151(19) 0.0002(16) -0.0101(18) -0.0024(19) C6 0.050(3) 0.018(2) 0.019(2) -0.0019(16) -0.0074(18) -0.0049(18) C7 0.0225(18) 0.0183(19) 0.022(2) 0.0012(16) -0.0054(15) -0.0002(15) C8 0.040(2) 0.022(2) 0.025(2) 0.0023(17) -0.0037(17) -0.0099(18) C9 0.049(3) 0.020(2) 0.035(2) 0.0047(18) -0.007(2) -0.0075(19) C10 0.040(2) 0.026(2) 0.025(2) 0.0072(17) -0.0081(18) -0.0073(18) C11 0.0214(18) 0.0199(19) 0.024(2) 0.0023(16) -0.0055(15) -0.0031(15) C12 0.032(2) 0.030(2) 0.0162(19) 0.0021(16) -0.0024(16) -0.0076(17) C13 0.052(3) 0.041(3) 0.019(2) -0.0028(19) -0.0022(19) -0.011(2) C14 0.032(2) 0.024(2) 0.0171(19) -0.0027(16) -0.0017(16) -0.0028(17) C15 0.029(2) 0.0215(19) 0.0184(19) -0.0009(15) -0.0028(15) -0.0062(16) C16 0.041(2) 0.0168(19) 0.029(2) -0.0054(17) -0.0045(18) -0.0052(17) C17 0.037(2) 0.019(2) 0.031(2) 0.0045(17) -0.0078(18) -0.0046(17) C18 0.030(2) 0.022(2) 0.023(2) 0.0033(16) -0.0036(16) -0.0048(17) C19 0.0209(18) 0.0181(18) 0.0188(19) 0.0003(15) -0.0040(14) -0.0050(15) C20 0.0192(17) 0.0213(19) 0.0199(19) 0.0003(15) -0.0062(14) -0.0037(15) N1 0.0275(17) 0.0158(16) 0.0244(17) -0.0008(13) -0.0030(13) -0.0039(13) N2 0.0226(15) 0.0167(15) 0.0178(16) 0.0010(12) -0.0054(12) -0.0042(12) N3 0.052(2) 0.033(2) 0.0258(19) -0.0053(16) -0.0051(17) -0.0068(18) N4 0.040(2) 0.0277(19) 0.0202(18) 0.0053(15) -0.0045(15) -0.0036(16) O1 0.0290(15) 0.0196(14) 0.0465(18) 0.0009(13) -0.0153(13) -0.0057(12) O2 0.068(2) 0.0237(15) 0.0187(15) 0.0041(12) -0.0058(14) -0.0064(15) O3 0.0241(14) 0.0228(14) 0.0412(17) -0.0014(13) -0.0035(12) -0.0040(12) O4 0.0439(16) 0.0149(13) 0.0238(15) 0.0013(11) -0.0096(12) -0.0010(12) O5 0.0379(16) 0.0170(13) 0.0230(15) 0.0000(11) -0.0059(12) 0.0023(12) O6 0.0257(13) 0.0241(14) 0.0209(14) -0.0012(11) -0.0067(11) -0.0081(11) O1W 0.107(4) 0.050(2) 0.060(3) 0.008(2) -0.024(2) -0.038(2) O2W 0.100(6) 0.040(4) 0.042(4) -0.005(3) -0.005(4) -0.031(4) S1 0.0197(4) 0.0134(4) 0.0172(4) 0.0010(3) -0.0045(3) -0.0031(3) Gd1 0.02011(11) 0.01241(11) 0.01636(11) 0.00035(7) -0.00431(7) -0.00236(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.372(5) . ? C1 C2 1.382(5) . ? C1 S1 1.772(4) . ? C2 C3 1.386(5) . ? C2 H2 0.9300 . ? C3 C4 1.390(5) . ? C3 H3 0.9300 . ? C4 C5 1.384(6) . ? C4 C7 1.516(5) . ? C5 C6 1.376(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O5 1.265(5) . ? C7 O4 1.259(5) . ? C8 N1 1.325(5) . ? C8 C9 1.402(6) . ? C8 H8 0.9300 . ? C9 C10 1.355(6) . ? C9 H9 0.9300 . ? C10 C11 1.398(5) . ? C10 H10 0.9300 . ? C11 C20 1.423(5) . ? C11 C12 1.429(6) . ? C12 N4 1.384(5) . ? C12 C14 1.357(6) . ? C13 N3 1.330(6) . ? C13 N4 1.343(6) . ? C13 H13 0.9300 . ? C14 N3 1.383(5) . ? C14 C15 1.449(5) . ? C15 C16 1.391(5) . ? C15 C19 1.414(5) . ? C16 C17 1.371(6) . ? C16 H16 0.9300 . ? C17 C18 1.384(6) . ? C17 H17 0.9300 . ? C18 N2 1.326(5) . ? C18 H18 0.9300 . ? C19 N2 1.363(5) . ? C19 C20 1.452(5) . ? C20 N1 1.361(5) . ? N1 Gd1 2.594(3) . ? N2 Gd1 2.603(3) . ? N4 H4 0.8600 . ? O1 S1 1.454(3) . ? O1 Gd1 2.412(3) 2_665 ? O2 S1 1.444(3) . ? O3 S1 1.447(3) . ? O3 Gd1 2.420(3) 2_565 ? O4 Gd1 2.423(3) 2_655 ? O5 Gd1 2.367(3) . ? O6 Gd1 2.312(3) . ? O6 Gd1 2.339(3) 2_655 ? O6 H6A 0.8512 . ? O1W H1WA 0.8528 . ? O1W H1WB 0.8498 . ? O2W H2WA 0.8498 . ? O2W H2WB 0.8544 . ? Gd1 O6 2.339(3) 2_655 ? Gd1 O1 2.412(3) 2_665 ? Gd1 O3 2.420(3) 2_565 ? Gd1 O4 2.423(3) 2_655 ? Gd1 Gd1 3.6330(4) 2_655 ? 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 C6 C1 C2 120.8(3) . . ? C6 C1 S1 119.4(3) . . ? C2 C1 S1 119.8(3) . . ? C3 C2 C1 119.3(4) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.4(4) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 118.8(3) . . ? C5 C4 C7 121.0(3) . . ? C3 C4 C7 120.2(3) . . ? C4 C5 C6 121.0(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 119.6(4) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O5 C7 O4 124.8(3) . . ? O5 C7 C4 116.9(3) . . ? O4 C7 C4 118.3(3) . . ? N1 C8 C9 123.8(4) . . ? N1 C8 H8 118.1 . . ? C9 C8 H8 118.1 . . ? C10 C9 C8 118.6(4) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C9 C10 C11 119.7(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C20 C11 C10 118.7(4) . . ? C20 C11 C12 115.7(3) . . ? C10 C11 C12 125.5(4) . . ? N4 C12 C14 105.4(4) . . ? N4 C12 C11 130.1(4) . . ? C14 C12 C11 124.5(3) . . ? N3 C13 N4 113.8(4) . . ? N3 C13 H13 123.1 . . ? N4 C13 H13 123.1 . . ? N3 C14 C12 111.7(3) . . ? N3 C14 C15 127.4(4) . . ? C12 C14 C15 120.9(4) . . ? C16 C15 C19 118.9(3) . . ? C16 C15 C14 124.1(4) . . ? C19 C15 C14 117.0(3) . . ? C17 C16 C15 119.2(4) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 118.6(4) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? N2 C18 C17 124.3(4) . . ? N2 C18 H18 117.8 . . ? C17 C18 H18 117.8 . . ? N2 C19 C15 121.0(3) . . ? N2 C19 C20 117.9(3) . . ? C15 C19 C20 121.0(3) . . ? N1 C20 C11 120.7(3) . . ? N1 C20 C19 118.5(3) . . ? C11 C20 C19 120.9(3) . . ? C8 N1 C20 118.4(3) . . ? C8 N1 Gd1 121.6(3) . . ? C20 N1 Gd1 120.0(2) . . ? C18 N2 C19 117.9(3) . . ? C18 N2 Gd1 122.2(2) . . ? C19 N2 Gd1 119.9(2) . . ? C13 N3 C14 102.8(4) . . ? C13 N4 C12 106.2(3) . . ? C13 N4 H4 126.9 . . ? C12 N4 H4 126.9 . . ? S1 O1 Gd1 155.35(17) . 2_665 ? S1 O3 Gd1 165.33(18) . 2_565 ? C7 O4 Gd1 134.1(2) . 2_655 ? C7 O5 Gd1 133.1(2) . . ? Gd1 O6 Gd1 102.71(9) . 2_655 ? Gd1 O6 H6A 149.6 . . ? Gd1 O6 H6A 53.3 2_655 . ? H1WA O1W H1WB 111.4 . . ? H2WA O2W H2WB 100.3 . . ? O2 S1 O1 113.26(18) . . ? O2 S1 O3 113.23(18) . . ? O1 S1 O3 109.02(17) . . ? O2 S1 C1 107.13(18) . . ? O1 S1 C1 107.11(17) . . ? O3 S1 C1 106.69(16) . . ? O6 Gd1 O6 77.28(9) . 2_655 ? O6 Gd1 O5 82.67(9) . . ? O6 Gd1 O5 72.95(9) 2_655 . ? O6 Gd1 O1 146.72(10) . 2_665 ? O6 Gd1 O1 76.69(9) 2_655 2_665 ? O5 Gd1 O1 108.83(9) . 2_665 ? O6 Gd1 O3 71.38(9) . 2_565 ? O6 Gd1 O3 139.18(9) 2_655 2_565 ? O5 Gd1 O3 77.64(9) . 2_565 ? O1 Gd1 O3 140.72(10) 2_665 2_565 ? O6 Gd1 O4 74.50(9) . 2_655 ? O6 Gd1 O4 76.74(9) 2_655 2_655 ? O5 Gd1 O4 145.32(9) . 2_655 ? O1 Gd1 O4 79.62(9) 2_665 2_655 ? O3 Gd1 O4 117.65(9) 2_565 2_655 ? O6 Gd1 N1 114.95(9) . . ? O6 Gd1 N1 145.44(9) 2_655 . ? O5 Gd1 N1 138.13(10) . . ? O1 Gd1 N1 77.75(10) 2_665 . ? O3 Gd1 N1 73.50(10) 2_565 . ? O4 Gd1 N1 76.09(9) 2_655 . ? O6 Gd1 N2 141.00(9) . . ? O6 Gd1 N2 127.82(9) 2_655 . ? O5 Gd1 N2 78.80(9) . . ? O1 Gd1 N2 72.21(10) 2_665 . ? O3 Gd1 N2 71.27(9) 2_565 . ? O4 Gd1 N2 134.49(9) 2_655 . ? N1 Gd1 N2 63.63(9) . . ? O6 Gd1 Gd1 38.91(6) . 2_655 ? O6 Gd1 Gd1 38.38(6) 2_655 2_655 ? O5 Gd1 Gd1 74.34(7) . 2_655 ? O1 Gd1 Gd1 112.57(7) 2_665 2_655 ? O3 Gd1 Gd1 106.50(7) 2_565 2_655 ? O4 Gd1 Gd1 71.47(6) 2_655 2_655 ? N1 Gd1 Gd1 143.01(7) . 2_655 ? N2 Gd1 Gd1 152.79(6) . 2_655 ? 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 C6 C1 C2 C3 -1.4(6) . . . . ? S1 C1 C2 C3 179.2(3) . . . . ? C1 C2 C3 C4 0.4(6) . . . . ? C2 C3 C4 C5 0.7(6) . . . . ? C2 C3 C4 C7 -178.1(4) . . . . ? C3 C4 C5 C6 -1.0(6) . . . . ? C7 C4 C5 C6 177.8(4) . . . . ? C2 C1 C6 C5 1.2(6) . . . . ? S1 C1 C6 C5 -179.5(3) . . . . ? C4 C5 C6 C1 0.1(7) . . . . ? C5 C4 C7 O5 6.3(5) . . . . ? C3 C4 C7 O5 -175.0(4) . . . . ? C5 C4 C7 O4 -174.1(4) . . . . ? C3 C4 C7 O4 4.7(5) . . . . ? N1 C8 C9 C10 1.8(7) . . . . ? C8 C9 C10 C11 0.4(7) . . . . ? C9 C10 C11 C20 -1.2(6) . . . . ? C9 C10 C11 C12 178.2(4) . . . . ? C20 C11 C12 N4 179.8(4) . . . . ? C10 C11 C12 N4 0.4(7) . . . . ? C20 C11 C12 C14 0.7(6) . . . . ? C10 C11 C12 C14 -178.7(4) . . . . ? N4 C12 C14 N3 0.5(5) . . . . ? C11 C12 C14 N3 179.8(4) . . . . ? N4 C12 C14 C15 -179.6(4) . . . . ? C11 C12 C14 C15 -0.3(6) . . . . ? N3 C14 C15 C16 -2.3(7) . . . . ? C12 C14 C15 C16 177.9(4) . . . . ? N3 C14 C15 C19 178.7(4) . . . . ? C12 C14 C15 C19 -1.1(6) . . . . ? C19 C15 C16 C17 0.0(6) . . . . ? C14 C15 C16 C17 -179.0(4) . . . . ? C15 C16 C17 C18 -0.6(6) . . . . ? C16 C17 C18 N2 0.5(6) . . . . ? C16 C15 C19 N2 0.8(6) . . . . ? C14 C15 C19 N2 179.9(3) . . . . ? C16 C15 C19 C20 -177.0(4) . . . . ? C14 C15 C19 C20 2.1(5) . . . . ? C10 C11 C20 N1 -0.1(5) . . . . ? C12 C11 C20 N1 -179.6(3) . . . . ? C10 C11 C20 C19 179.8(4) . . . . ? C12 C11 C20 C19 0.3(5) . . . . ? N2 C19 C20 N1 0.3(5) . . . . ? C15 C19 C20 N1 178.2(3) . . . . ? N2 C19 C20 C11 -179.6(3) . . . . ? C15 C19 C20 C11 -1.7(5) . . . . ? C9 C8 N1 C20 -3.1(6) . . . . ? C9 C8 N1 Gd1 177.8(3) . . . . ? C11 C20 N1 C8 2.2(5) . . . . ? C19 C20 N1 C8 -177.7(4) . . . . ? C11 C20 N1 Gd1 -178.6(2) . . . . ? C19 C20 N1 Gd1 1.5(4) . . . . ? C17 C18 N2 C19 0.2(6) . . . . ? C17 C18 N2 Gd1 179.1(3) . . . . ? C15 C19 N2 C18 -0.9(5) . . . . ? C20 C19 N2 C18 177.0(3) . . . . ? C15 C19 N2 Gd1 -179.8(3) . . . . ? C20 C19 N2 Gd1 -2.0(4) . . . . ? N4 C13 N3 C14 0.9(5) . . . . ? C12 C14 N3 C13 -0.9(5) . . . . ? C15 C14 N3 C13 179.3(4) . . . . ? N3 C13 N4 C12 -0.6(5) . . . . ? C14 C12 N4 C13 0.0(5) . . . . ? C11 C12 N4 C13 -179.2(4) . . . . ? O5 C7 O4 Gd1 -19.9(6) . . . 2_655 ? C4 C7 O4 Gd1 160.5(2) . . . 2_655 ? O4 C7 O5 Gd1 7.0(6) . . . . ? C4 C7 O5 Gd1 -173.4(2) . . . . ? Gd1 O1 S1 O2 -90.2(5) 2_665 . . . ? Gd1 O1 S1 O3 142.8(4) 2_665 . . . ? Gd1 O1 S1 C1 27.7(5) 2_665 . . . ? Gd1 O3 S1 O2 58.2(7) 2_565 . . . ? Gd1 O3 S1 O1 -174.8(7) 2_565 . . . ? Gd1 O3 S1 C1 -59.4(7) 2_565 . . . ? C6 C1 S1 O2 166.6(3) . . . . ? C2 C1 S1 O2 -14.0(4) . . . . ? C6 C1 S1 O1 44.8(4) . . . . ? C2 C1 S1 O1 -135.8(3) . . . . ? C6 C1 S1 O3 -71.8(4) . . . . ? C2 C1 S1 O3 107.5(3) . . . . ? Gd1 O6 Gd1 O6 0.0 2_655 . . 2_655 ? Gd1 O6 Gd1 O5 74.09(10) 2_655 . . . ? Gd1 O6 Gd1 O1 -39.3(2) 2_655 . . 2_665 ? Gd1 O6 Gd1 O3 153.47(12) 2_655 . . 2_565 ? Gd1 O6 Gd1 O4 -79.55(10) 2_655 . . 2_655 ? Gd1 O6 Gd1 N1 -145.70(10) 2_655 . . . ? Gd1 O6 Gd1 N2 136.06(12) 2_655 . . . ? C7 O5 Gd1 O6 -35.9(3) . . . . ? C7 O5 Gd1 O6 43.0(3) . . . 2_655 ? C7 O5 Gd1 O1 112.0(3) . . . 2_665 ? C7 O5 Gd1 O3 -108.3(3) . . . 2_565 ? C7 O5 Gd1 O4 12.9(4) . . . 2_655 ? C7 O5 Gd1 N1 -155.5(3) . . . . ? C7 O5 Gd1 N2 178.6(4) . . . . ? C7 O5 Gd1 Gd1 3.0(3) . . . 2_655 ? C8 N1 Gd1 O6 40.9(3) . . . . ? C20 N1 Gd1 O6 -138.2(3) . . . . ? C8 N1 Gd1 O6 -63.4(4) . . . 2_655 ? C20 N1 Gd1 O6 117.4(3) . . . 2_655 ? C8 N1 Gd1 O5 148.9(3) . . . . ? C20 N1 Gd1 O5 -30.3(3) . . . . ? C8 N1 Gd1 O1 -106.5(3) . . . 2_665 ? C20 N1 Gd1 O1 74.4(3) . . . 2_665 ? C8 N1 Gd1 O3 100.6(3) . . . 2_565 ? C20 N1 Gd1 O3 -78.6(3) . . . 2_565 ? C8 N1 Gd1 O4 -24.3(3) . . . 2_655 ? C20 N1 Gd1 O4 156.5(3) . . . 2_655 ? C8 N1 Gd1 N2 177.5(3) . . . . ? C20 N1 Gd1 N2 -1.7(2) . . . . ? C8 N1 Gd1 Gd1 4.9(4) . . . 2_655 ? C20 N1 Gd1 Gd1 -174.3(2) . . . 2_655 ? C18 N2 Gd1 O6 -79.2(3) . . . . ? C19 N2 Gd1 O6 99.7(3) . . . . ? C18 N2 Gd1 O6 41.8(3) . . . 2_655 ? C19 N2 Gd1 O6 -139.3(2) . . . 2_655 ? C18 N2 Gd1 O5 -16.0(3) . . . . ? C19 N2 Gd1 O5 162.9(3) . . . . ? C18 N2 Gd1 O1 98.1(3) . . . 2_665 ? C19 N2 Gd1 O1 -83.0(3) . . . 2_665 ? C18 N2 Gd1 O3 -96.6(3) . . . 2_565 ? C19 N2 Gd1 O3 82.3(3) . . . 2_565 ? C18 N2 Gd1 O4 152.7(3) . . . 2_655 ? C19 N2 Gd1 O4 -28.4(3) . . . 2_655 ? C18 N2 Gd1 N1 -177.0(3) . . . . ? C19 N2 Gd1 N1 1.9(2) . . . . ? C18 N2 Gd1 Gd1 -6.8(4) . . . 2_655 ? C19 N2 Gd1 Gd1 172.08(18) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.724 _refine_diff_density_min -0.741 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 956198' ####################################################################### # # 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_130505b_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 N8 O15 S2 Sm2' _chemical_formula_weight 1229.56 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' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9200(4) _cell_length_b 10.1694(6) _cell_length_c 15.2822(9) _cell_angle_alpha 83.6210(10) _cell_angle_beta 78.0290(10) _cell_angle_gamma 77.6100(10) _cell_volume 1025.05(10) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2376 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 26.96 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.992 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 3.023 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7520 _exptl_absorpt_correction_T_max 0.9420 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5216 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3668 _reflns_number_gt 3386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0496P)^2^+0.2384P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3668 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1853(6) 0.6841(4) -0.1593(3) 0.0203(9) Uani 1 1 d . . . C2 C 0.2097(8) 0.5823(5) -0.2157(3) 0.0276(11) Uani 1 1 d . . . H2 H 0.1949 0.6029 -0.2751 0.033 Uiso 1 1 calc R . . C3 C 0.2565(7) 0.4489(4) -0.1829(3) 0.0250(10) Uani 1 1 d . . . H3 H 0.2724 0.3799 -0.2205 0.030 Uiso 1 1 calc R . . C4 C 0.2799(7) 0.4175(4) -0.0943(3) 0.0226(10) Uani 1 1 d . . . C5 C 0.2518(8) 0.5217(5) -0.0393(3) 0.0318(12) Uani 1 1 d . . . H5 H 0.2647 0.5017 0.0203 0.038 Uiso 1 1 calc R . . C6 C 0.2048(8) 0.6553(5) -0.0711(3) 0.0308(11) Uani 1 1 d . . . H6 H 0.1867 0.7245 -0.0333 0.037 Uiso 1 1 calc R . . C7 C 0.3357(7) 0.2724(4) -0.0600(3) 0.0230(10) Uani 1 1 d . . . C8 C 0.3805(8) -0.1661(5) 0.3080(3) 0.0292(11) Uani 1 1 d . . . H8 H 0.4133 -0.2257 0.2628 0.035 Uiso 1 1 calc R . . C9 C 0.3481(9) -0.2190(5) 0.3953(3) 0.0357(12) Uani 1 1 d . . . H9 H 0.3607 -0.3117 0.4081 0.043 Uiso 1 1 calc R . . C10 C 0.2971(8) -0.1339(5) 0.4630(3) 0.0326(12) Uani 1 1 d . . . H10 H 0.2741 -0.1676 0.5226 0.039 Uiso 1 1 calc R . . C11 C 0.2801(7) 0.0055(4) 0.4411(3) 0.0220(10) Uani 1 1 d . . . C12 C 0.2248(7) 0.1062(5) 0.5044(3) 0.0259(10) Uani 1 1 d . . . C13 C 0.1363(9) 0.2213(6) 0.6233(3) 0.0395(13) Uani 1 1 d . . . H13 H 0.0999 0.2410 0.6831 0.047 Uiso 1 1 calc R . . C14 C 0.2051(7) 0.2408(5) 0.4817(3) 0.0265(10) Uani 1 1 d . . . C15 C 0.2394(7) 0.2912(5) 0.3889(3) 0.0243(10) Uani 1 1 d . . . C16 C 0.2142(7) 0.4286(5) 0.3607(3) 0.0296(11) Uani 1 1 d . . . H16 H 0.1755 0.4939 0.4023 0.036 Uiso 1 1 calc R . . C17 C 0.2478(8) 0.4655(5) 0.2701(3) 0.0311(11) Uani 1 1 d . . . H17 H 0.2301 0.5561 0.2496 0.037 Uiso 1 1 calc R . . C18 C 0.3086(7) 0.3649(5) 0.2098(3) 0.0261(10) Uani 1 1 d . . . H18 H 0.3340 0.3910 0.1489 0.031 Uiso 1 1 calc R . . C19 C 0.2985(6) 0.1957(4) 0.3238(3) 0.0177(9) Uani 1 1 d . . . C20 C 0.3173(6) 0.0518(4) 0.3498(3) 0.0201(9) Uani 1 1 d . . . N1 N 0.3681(6) -0.0352(4) 0.2839(3) 0.0230(8) Uani 1 1 d . . . N2 N 0.3323(5) 0.2346(3) 0.2341(2) 0.0198(8) Uani 1 1 d . . . N3 N 0.1498(7) 0.3151(4) 0.5562(3) 0.0357(10) Uani 1 1 d . . . N4 N 0.1799(7) 0.0949(4) 0.5969(3) 0.0342(10) Uani 1 1 d . . . H4 H 0.1799 0.0216 0.6309 0.041 Uiso 1 1 calc R . . O1 O 0.2594(5) 0.9262(3) -0.1688(2) 0.0319(8) Uani 1 1 d . . . O2 O 0.1632(6) 0.8558(3) -0.2965(2) 0.0384(9) Uani 1 1 d . . . O3 O -0.0784(5) 0.9065(3) -0.1606(2) 0.0325(8) Uani 1 1 d . . . O4 O 0.3762(5) 0.1830(3) -0.1149(2) 0.0314(8) Uani 1 1 d . . . O5 O 0.3405(5) 0.2510(3) 0.0229(2) 0.0275(7) Uani 1 1 d . . . O6 O 0.3117(5) -0.0487(3) 0.0174(2) 0.0238(7) Uani 1 1 d . . . H6A H 0.2949 -0.0560 -0.0356 0.036 Uiso 1 1 d R . . O1W O 0.9072(8) 0.2303(5) 0.8542(3) 0.0688(14) Uani 1 1 d . . . H1WA H 1.0284 0.2179 0.8629 0.103 Uiso 1 1 d R . . H1WB H 0.8586 0.1593 0.8691 0.103 Uiso 1 1 d R . . O2W O 0.6922(15) 0.4509(8) 0.4403(5) 0.052(2) Uani 0.50 1 d P . . H2WA H 0.7434 0.5210 0.4346 0.079 Uiso 0.50 1 d PR . . H2WB H 0.5793 0.4785 0.4747 0.079 Uiso 0.50 1 d PR . . S1 S 0.12951(15) 0.85492(10) -0.20046(7) 0.0176(2) Uani 1 1 d . . . Sm1 Sm 0.44307(3) 0.05232(2) 0.115243(14) 0.01724(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.019(2) 0.016(2) 0.026(2) 0.0005(18) -0.0055(18) -0.0025(18) C2 0.040(3) 0.020(2) 0.022(2) -0.0001(19) -0.013(2) 0.001(2) C3 0.037(3) 0.014(2) 0.024(2) -0.0047(18) -0.012(2) 0.002(2) C4 0.022(2) 0.018(2) 0.025(2) -0.0011(18) -0.0014(18) -0.0025(18) C5 0.051(3) 0.025(3) 0.018(2) 0.003(2) -0.008(2) -0.004(2) C6 0.052(3) 0.019(2) 0.020(2) -0.0009(19) -0.007(2) -0.004(2) C7 0.026(2) 0.016(2) 0.026(3) 0.0051(19) -0.0047(19) -0.0046(19) C8 0.038(3) 0.018(2) 0.030(3) -0.002(2) -0.003(2) -0.005(2) C9 0.054(3) 0.016(2) 0.038(3) 0.004(2) -0.011(3) -0.009(2) C10 0.039(3) 0.028(3) 0.028(3) 0.008(2) -0.005(2) -0.006(2) C11 0.022(2) 0.018(2) 0.025(2) 0.0041(18) -0.0065(19) -0.0032(18) C12 0.028(3) 0.029(3) 0.020(2) 0.0010(19) -0.0050(19) -0.003(2) C13 0.054(4) 0.044(3) 0.018(3) -0.007(2) -0.002(2) -0.007(3) C14 0.035(3) 0.021(2) 0.021(2) -0.0010(19) -0.004(2) -0.004(2) C15 0.026(2) 0.022(2) 0.024(2) 0.0020(19) -0.0037(19) -0.0066(19) C16 0.036(3) 0.020(2) 0.030(3) -0.005(2) -0.001(2) -0.003(2) C17 0.038(3) 0.017(2) 0.035(3) -0.001(2) -0.002(2) -0.004(2) C18 0.025(2) 0.023(2) 0.027(3) 0.004(2) -0.002(2) -0.003(2) C19 0.017(2) 0.016(2) 0.019(2) 0.0007(17) -0.0043(17) -0.0019(17) C20 0.020(2) 0.017(2) 0.023(2) 0.0031(18) -0.0078(18) -0.0017(18) N1 0.026(2) 0.0137(19) 0.028(2) 0.0010(16) -0.0055(16) -0.0010(16) N2 0.024(2) 0.0137(19) 0.0213(19) 0.0006(15) -0.0060(15) -0.0023(15) N3 0.049(3) 0.032(2) 0.022(2) -0.0016(18) -0.0012(19) -0.004(2) N4 0.048(3) 0.030(2) 0.021(2) 0.0037(18) -0.0009(19) -0.008(2) O1 0.0286(18) 0.0216(18) 0.050(2) 0.0015(15) -0.0171(16) -0.0087(14) O2 0.068(3) 0.0263(19) 0.0170(17) 0.0027(14) -0.0041(17) -0.0064(18) O3 0.0196(17) 0.0235(18) 0.051(2) 0.0011(16) -0.0031(15) -0.0019(14) O4 0.047(2) 0.0150(17) 0.0295(19) -0.0009(14) -0.0109(16) 0.0027(15) O5 0.039(2) 0.0155(16) 0.0244(18) 0.0056(13) -0.0062(14) -0.0001(14) O6 0.0267(17) 0.0266(17) 0.0195(16) -0.0050(13) -0.0023(13) -0.0081(14) O1W 0.096(4) 0.052(3) 0.065(3) 0.012(2) -0.020(3) -0.034(3) O2W 0.099(7) 0.031(4) 0.035(4) 0.001(3) -0.012(4) -0.033(4) S1 0.0188(5) 0.0136(5) 0.0192(5) 0.0021(4) -0.0047(4) -0.0016(4) Sm1 0.02036(14) 0.01268(14) 0.01770(14) 0.00026(9) -0.00392(9) -0.00148(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.375(7) . ? C1 C2 1.382(6) . ? C1 S1 1.770(4) . ? C2 C3 1.386(6) . ? C2 H2 0.9300 . ? C3 C4 1.392(6) . ? C3 H3 0.9300 . ? C4 C5 1.381(6) . ? C4 C7 1.506(6) . ? C5 C6 1.384(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O4 1.254(5) . ? C7 O5 1.267(5) . ? C8 N1 1.330(6) . ? C8 C9 1.374(7) . ? C8 H8 0.9300 . ? C9 C10 1.363(7) . ? C9 H9 0.9300 . ? C10 C11 1.405(7) . ? C10 H10 0.9300 . ? C11 C20 1.412(6) . ? C11 C12 1.425(6) . ? C12 C14 1.359(7) . ? C12 N4 1.380(6) . ? C13 N3 1.323(7) . ? C13 N4 1.342(7) . ? C13 H13 0.9300 . ? C14 N3 1.379(6) . ? C14 C15 1.442(6) . ? C15 C16 1.401(6) . ? C15 C19 1.406(6) . ? C16 C17 1.378(7) . ? C16 H16 0.9300 . ? C17 C18 1.391(7) . ? C17 H17 0.9300 . ? C18 N2 1.320(6) . ? C18 H18 0.9300 . ? C19 N2 1.371(5) . ? C19 C20 1.458(6) . ? C20 N1 1.355(6) . ? N1 Sm1 2.615(4) . ? N2 Sm1 2.624(4) . ? N4 H4 0.8600 . ? O1 S1 1.452(3) . ? O1 Sm1 2.426(3) 2_665 ? O2 S1 1.437(3) . ? O3 S1 1.449(3) . ? O3 Sm1 2.431(3) 2_565 ? O4 Sm1 2.451(3) 2_655 ? O5 Sm1 2.397(3) . ? O6 Sm1 2.329(3) . ? O6 Sm1 2.357(3) 2_655 ? O6 H6A 0.8548 . ? O1W H1WA 0.8560 . ? O1W H1WB 0.8501 . ? O2W H2WA 0.8506 . ? O2W H2WB 0.8572 . ? Sm1 O6 2.357(3) 2_655 ? Sm1 O1 2.426(3) 2_665 ? Sm1 O3 2.431(3) 2_565 ? Sm1 O4 2.451(3) 2_655 ? Sm1 Sm1 3.6718(5) 2_655 ? 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 C6 C1 C2 121.1(4) . . ? C6 C1 S1 119.0(3) . . ? C2 C1 S1 119.9(3) . . ? C1 C2 C3 119.3(4) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 120.6(4) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 118.6(4) . . ? C5 C4 C7 121.3(4) . . ? C3 C4 C7 120.1(4) . . ? C4 C5 C6 121.5(4) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 118.9(4) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? O4 C7 O5 125.2(4) . . ? O4 C7 C4 118.2(4) . . ? O5 C7 C4 116.6(4) . . ? N1 C8 C9 124.3(5) . . ? N1 C8 H8 117.9 . . ? C9 C8 H8 117.9 . . ? C10 C9 C8 119.2(4) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 118.8(5) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C11 C20 118.6(4) . . ? C10 C11 C12 125.0(4) . . ? C20 C11 C12 116.4(4) . . ? C14 C12 N4 105.2(4) . . ? C14 C12 C11 124.0(4) . . ? N4 C12 C11 130.8(4) . . ? N3 C13 N4 113.9(4) . . ? N3 C13 H13 123.1 . . ? N4 C13 H13 123.1 . . ? C12 C14 N3 111.8(4) . . ? C12 C14 C15 120.8(4) . . ? N3 C14 C15 127.4(4) . . ? C16 C15 C19 118.8(4) . . ? C16 C15 C14 123.8(4) . . ? C19 C15 C14 117.4(4) . . ? C17 C16 C15 118.9(4) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C16 C17 C18 118.9(4) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? N2 C18 C17 123.8(4) . . ? N2 C18 H18 118.1 . . ? C17 C18 H18 118.1 . . ? N2 C19 C15 121.3(4) . . ? N2 C19 C20 117.8(4) . . ? C15 C19 C20 120.8(4) . . ? N1 C20 C11 121.3(4) . . ? N1 C20 C19 118.1(4) . . ? C11 C20 C19 120.5(4) . . ? C8 N1 C20 117.8(4) . . ? C8 N1 Sm1 121.4(3) . . ? C20 N1 Sm1 120.8(3) . . ? C18 N2 C19 118.3(4) . . ? C18 N2 Sm1 121.6(3) . . ? C19 N2 Sm1 120.1(3) . . ? C13 N3 C14 102.9(4) . . ? C13 N4 C12 106.3(4) . . ? C13 N4 H4 126.9 . . ? C12 N4 H4 126.9 . . ? S1 O1 Sm1 155.5(2) . 2_665 ? S1 O3 Sm1 165.0(2) . 2_565 ? C7 O4 Sm1 134.3(3) . 2_655 ? C7 O5 Sm1 133.2(3) . . ? Sm1 O6 Sm1 103.19(11) . 2_655 ? Sm1 O6 H6A 150.1 . . ? Sm1 O6 H6A 53.3 2_655 . ? H1WA O1W H1WB 111.4 . . ? H2WA O2W H2WB 100.2 . . ? O2 S1 O3 113.2(2) . . ? O2 S1 O1 113.3(2) . . ? O3 S1 O1 109.3(2) . . ? O2 S1 C1 106.9(2) . . ? O3 S1 C1 106.4(2) . . ? O1 S1 C1 107.4(2) . . ? O6 Sm1 O6 76.81(11) . 2_655 ? O6 Sm1 O5 82.23(11) . . ? O6 Sm1 O5 72.75(11) 2_655 . ? O6 Sm1 O1 146.99(11) . 2_665 ? O6 Sm1 O1 77.27(11) 2_655 2_665 ? O5 Sm1 O1 108.96(11) . 2_665 ? O6 Sm1 O3 71.38(11) . 2_565 ? O6 Sm1 O3 138.99(12) 2_655 2_565 ? O5 Sm1 O3 77.84(11) . 2_565 ? O1 Sm1 O3 140.45(12) 2_665 2_565 ? O6 Sm1 O4 74.45(11) . 2_655 ? O6 Sm1 O4 76.47(11) 2_655 2_655 ? O5 Sm1 O4 144.82(11) . 2_655 ? O1 Sm1 O4 79.90(11) 2_665 2_655 ? O3 Sm1 O4 117.53(11) 2_565 2_655 ? O6 Sm1 N1 115.81(11) . . ? O6 Sm1 N1 145.48(11) 2_655 . ? O5 Sm1 N1 138.11(11) . . ? O1 Sm1 N1 77.04(12) 2_665 . ? O3 Sm1 N1 73.68(12) 2_565 . ? O4 Sm1 N1 76.64(11) 2_655 . ? O6 Sm1 N2 140.80(11) . . ? O6 Sm1 N2 128.32(11) 2_655 . ? O5 Sm1 N2 79.12(11) . . ? O1 Sm1 N2 72.13(11) 2_665 . ? O3 Sm1 N2 71.14(12) 2_565 . ? O4 Sm1 N2 134.72(11) 2_655 . ? N1 Sm1 N2 63.01(11) . . ? O6 Sm1 Sm1 38.68(7) . 2_655 ? O6 Sm1 Sm1 38.13(7) 2_655 2_655 ? O5 Sm1 Sm1 73.98(8) . 2_655 ? O1 Sm1 Sm1 112.98(9) 2_665 2_655 ? O3 Sm1 Sm1 106.37(9) 2_565 2_655 ? O4 Sm1 Sm1 71.33(8) 2_655 2_655 ? N1 Sm1 Sm1 143.60(8) . 2_655 ? N2 Sm1 Sm1 152.80(8) . 2_655 ? 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 C6 C1 C2 C3 -0.6(7) . . . . ? S1 C1 C2 C3 179.0(4) . . . . ? C1 C2 C3 C4 -0.3(7) . . . . ? C2 C3 C4 C5 1.2(7) . . . . ? C2 C3 C4 C7 -178.5(4) . . . . ? C3 C4 C5 C6 -1.2(8) . . . . ? C7 C4 C5 C6 178.6(5) . . . . ? C2 C1 C6 C5 0.7(8) . . . . ? S1 C1 C6 C5 -178.9(4) . . . . ? C4 C5 C6 C1 0.2(8) . . . . ? C5 C4 C7 O4 -173.9(5) . . . . ? C3 C4 C7 O4 5.8(7) . . . . ? C5 C4 C7 O5 5.1(7) . . . . ? C3 C4 C7 O5 -175.2(4) . . . . ? N1 C8 C9 C10 0.9(9) . . . . ? C8 C9 C10 C11 -0.2(8) . . . . ? C9 C10 C11 C20 -0.2(7) . . . . ? C9 C10 C11 C12 178.8(5) . . . . ? C10 C11 C12 C14 -178.5(5) . . . . ? C20 C11 C12 C14 0.5(7) . . . . ? C10 C11 C12 N4 1.2(8) . . . . ? C20 C11 C12 N4 -179.8(5) . . . . ? N4 C12 C14 N3 0.1(6) . . . . ? C11 C12 C14 N3 179.8(4) . . . . ? N4 C12 C14 C15 -179.5(4) . . . . ? C11 C12 C14 C15 0.3(8) . . . . ? C12 C14 C15 C16 177.4(5) . . . . ? N3 C14 C15 C16 -2.0(8) . . . . ? C12 C14 C15 C19 -1.6(7) . . . . ? N3 C14 C15 C19 179.0(5) . . . . ? C19 C15 C16 C17 0.1(7) . . . . ? C14 C15 C16 C17 -178.9(5) . . . . ? C15 C16 C17 C18 -1.0(7) . . . . ? C16 C17 C18 N2 1.5(8) . . . . ? C16 C15 C19 N2 0.3(7) . . . . ? C14 C15 C19 N2 179.3(4) . . . . ? C16 C15 C19 C20 -177.0(4) . . . . ? C14 C15 C19 C20 2.0(6) . . . . ? C10 C11 C20 N1 0.1(7) . . . . ? C12 C11 C20 N1 -179.0(4) . . . . ? C10 C11 C20 C19 179.1(4) . . . . ? C12 C11 C20 C19 0.0(6) . . . . ? N2 C19 C20 N1 0.4(6) . . . . ? C15 C19 C20 N1 177.8(4) . . . . ? N2 C19 C20 C11 -178.6(4) . . . . ? C15 C19 C20 C11 -1.3(6) . . . . ? C9 C8 N1 C20 -1.0(7) . . . . ? C9 C8 N1 Sm1 178.3(4) . . . . ? C11 C20 N1 C8 0.5(6) . . . . ? C19 C20 N1 C8 -178.5(4) . . . . ? C11 C20 N1 Sm1 -178.8(3) . . . . ? C19 C20 N1 Sm1 2.2(5) . . . . ? C17 C18 N2 C19 -1.1(7) . . . . ? C17 C18 N2 Sm1 179.2(4) . . . . ? C15 C19 N2 C18 0.2(6) . . . . ? C20 C19 N2 C18 177.6(4) . . . . ? C15 C19 N2 Sm1 179.9(3) . . . . ? C20 C19 N2 Sm1 -2.7(5) . . . . ? N4 C13 N3 C14 0.5(6) . . . . ? C12 C14 N3 C13 -0.3(6) . . . . ? C15 C14 N3 C13 179.2(5) . . . . ? N3 C13 N4 C12 -0.4(7) . . . . ? C14 C12 N4 C13 0.2(6) . . . . ? C11 C12 N4 C13 -179.5(5) . . . . ? O5 C7 O4 Sm1 -18.4(7) . . . 2_655 ? C4 C7 O4 Sm1 160.6(3) . . . 2_655 ? O4 C7 O5 Sm1 5.3(7) . . . . ? C4 C7 O5 Sm1 -173.7(3) . . . . ? Sm1 O3 S1 O2 55.3(9) 2_565 . . . ? Sm1 O3 S1 O1 -177.5(8) 2_565 . . . ? Sm1 O3 S1 C1 -61.8(9) 2_565 . . . ? Sm1 O1 S1 O2 -93.1(5) 2_665 . . . ? Sm1 O1 S1 O3 139.8(5) 2_665 . . . ? Sm1 O1 S1 C1 24.7(6) 2_665 . . . ? C6 C1 S1 O2 167.1(4) . . . . ? C2 C1 S1 O2 -12.5(4) . . . . ? C6 C1 S1 O3 -71.7(4) . . . . ? C2 C1 S1 O3 108.7(4) . . . . ? C6 C1 S1 O1 45.2(4) . . . . ? C2 C1 S1 O1 -134.4(4) . . . . ? Sm1 O6 Sm1 O6 0.0 2_655 . . 2_655 ? Sm1 O6 Sm1 O5 74.02(12) 2_655 . . . ? Sm1 O6 Sm1 O1 -39.1(2) 2_655 . . 2_665 ? Sm1 O6 Sm1 O3 153.74(14) 2_655 . . 2_565 ? Sm1 O6 Sm1 O4 -79.39(12) 2_655 . . 2_655 ? Sm1 O6 Sm1 N1 -145.75(11) 2_655 . . . ? Sm1 O6 Sm1 N2 136.07(14) 2_655 . . . ? C7 O5 Sm1 O6 -34.8(4) . . . . ? C7 O5 Sm1 O6 43.8(4) . . . 2_655 ? C7 O5 Sm1 O1 113.2(4) . . . 2_665 ? C7 O5 Sm1 O3 -107.3(4) . . . 2_565 ? C7 O5 Sm1 O4 13.7(5) . . . 2_655 ? C7 O5 Sm1 N1 -155.2(4) . . . . ? C7 O5 Sm1 N2 179.9(4) . . . . ? C7 O5 Sm1 Sm1 3.9(4) . . . 2_655 ? C8 N1 Sm1 O6 42.2(4) . . . . ? C20 N1 Sm1 O6 -138.5(3) . . . . ? C8 N1 Sm1 O6 -62.6(4) . . . 2_655 ? C20 N1 Sm1 O6 116.7(3) . . . 2_655 ? C8 N1 Sm1 O5 150.6(3) . . . . ? C20 N1 Sm1 O5 -30.2(4) . . . . ? C8 N1 Sm1 O1 -105.4(4) . . . 2_665 ? C20 N1 Sm1 O1 73.9(3) . . . 2_665 ? C8 N1 Sm1 O3 101.5(4) . . . 2_565 ? C20 N1 Sm1 O3 -79.2(3) . . . 2_565 ? C8 N1 Sm1 O4 -22.9(4) . . . 2_655 ? C20 N1 Sm1 O4 156.4(3) . . . 2_655 ? C8 N1 Sm1 N2 178.3(4) . . . . ? C20 N1 Sm1 N2 -2.5(3) . . . . ? C8 N1 Sm1 Sm1 5.9(5) . . . 2_655 ? C20 N1 Sm1 Sm1 -174.8(2) . . . 2_655 ? C18 N2 Sm1 O6 -79.2(4) . . . . ? C19 N2 Sm1 O6 101.2(3) . . . . ? C18 N2 Sm1 O6 41.4(4) . . . 2_655 ? C19 N2 Sm1 O6 -138.2(3) . . . 2_655 ? C18 N2 Sm1 O5 -16.1(3) . . . . ? C19 N2 Sm1 O5 164.2(3) . . . . ? C18 N2 Sm1 O1 98.1(4) . . . 2_665 ? C19 N2 Sm1 O1 -81.6(3) . . . 2_665 ? C18 N2 Sm1 O3 -96.9(4) . . . 2_565 ? C19 N2 Sm1 O3 83.5(3) . . . 2_565 ? C18 N2 Sm1 O4 152.7(3) . . . 2_655 ? C19 N2 Sm1 O4 -27.0(4) . . . 2_655 ? C18 N2 Sm1 N1 -177.7(4) . . . . ? C19 N2 Sm1 N1 2.6(3) . . . . ? C18 N2 Sm1 Sm1 -7.6(5) . . . 2_655 ? C19 N2 Sm1 Sm1 172.7(2) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.743 _refine_diff_density_min -0.679 _refine_diff_density_rms 0.118 _database_code_depnum_ccdc_archive 'CCDC 956199' ####################################################################### # # 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_121014a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 N8 O15 S2 Tb2' _chemical_formula_weight 1246.70 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' 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' 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 6.8766(7) _cell_length_b 10.1482(10) _cell_length_c 15.1965(15) _cell_angle_alpha 83.857(2) _cell_angle_beta 78.023(2) _cell_angle_gamma 77.275(2) _cell_volume 1009.83(17) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1022 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 20.70 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.050 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 610 _exptl_absorpt_coefficient_mu 3.663 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7109 _exptl_absorpt_correction_T_max 0.9303 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5093 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0768 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3617 _reflns_number_gt 3044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.2384P] 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 3617 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1862(10) 0.6825(7) -0.1575(5) 0.0163(16) Uani 1 1 d . . . C2 C 0.2055(12) 0.5804(8) -0.2142(5) 0.0271(19) Uani 1 1 d . . . H2 H 0.1879 0.6010 -0.2735 0.033 Uiso 1 1 calc R . . C3 C 0.2513(12) 0.4480(7) -0.1811(5) 0.0249(18) Uani 1 1 d . . . H3 H 0.2653 0.3787 -0.2188 0.030 Uiso 1 1 calc R . . C4 C 0.2771(11) 0.4158(7) -0.0922(5) 0.0219(17) Uani 1 1 d . . . C5 C 0.2512(13) 0.5205(8) -0.0371(5) 0.030(2) Uani 1 1 d . . . H5 H 0.2648 0.5006 0.0228 0.036 Uiso 1 1 calc R . . C6 C 0.2053(12) 0.6545(8) -0.0692(5) 0.0272(19) Uani 1 1 d . . . H6 H 0.1878 0.7242 -0.0315 0.033 Uiso 1 1 calc R . . C7 C 0.3332(12) 0.2705(8) -0.0573(5) 0.0226(17) Uani 1 1 d . . . C8 C 0.3803(12) -0.1676(8) 0.3038(5) 0.0256(18) Uani 1 1 d . . . H8 H 0.4101 -0.2269 0.2580 0.031 Uiso 1 1 calc R . . C9 C 0.3506(13) -0.2210(8) 0.3917(6) 0.033(2) Uani 1 1 d . . . H9 H 0.3645 -0.3140 0.4041 0.040 Uiso 1 1 calc R . . C10 C 0.3013(12) -0.1369(8) 0.4594(6) 0.0285(19) Uani 1 1 d . . . H10 H 0.2813 -0.1713 0.5191 0.034 Uiso 1 1 calc R . . C11 C 0.2804(11) 0.0032(8) 0.4387(5) 0.0214(17) Uani 1 1 d . . . C12 C 0.2240(12) 0.1040(8) 0.5037(5) 0.0254(18) Uani 1 1 d . . . C13 C 0.1385(13) 0.2190(9) 0.6227(6) 0.034(2) Uani 1 1 d . . . H13 H 0.1017 0.2387 0.6830 0.041 Uiso 1 1 calc R . . C14 C 0.2044(12) 0.2402(8) 0.4809(5) 0.0233(17) Uani 1 1 d . . . C15 C 0.2406(11) 0.2899(8) 0.3879(5) 0.0213(17) Uani 1 1 d . . . C16 C 0.2159(13) 0.4278(8) 0.3599(5) 0.0279(19) Uani 1 1 d . . . H16 H 0.1772 0.4930 0.4022 0.034 Uiso 1 1 calc R . . C17 C 0.2490(12) 0.4654(8) 0.2702(5) 0.0286(19) Uani 1 1 d . . . H17 H 0.2322 0.5563 0.2501 0.034 Uiso 1 1 calc R . . C18 C 0.3090(11) 0.3638(7) 0.2088(6) 0.0240(18) Uani 1 1 d . . . H18 H 0.3333 0.3904 0.1477 0.029 Uiso 1 1 calc R . . C19 C 0.2984(10) 0.1948(7) 0.3219(5) 0.0165(16) Uani 1 1 d . . . C20 C 0.3183(11) 0.0505(7) 0.3479(5) 0.0183(16) Uani 1 1 d . . . N1 N 0.3689(9) -0.0364(6) 0.2805(4) 0.0206(14) Uani 1 1 d . . . N2 N 0.3334(9) 0.2324(6) 0.2320(4) 0.0192(14) Uani 1 1 d . . . N3 N 0.1526(11) 0.3125(7) 0.5555(5) 0.0330(17) Uani 1 1 d . . . N4 N 0.1828(11) 0.0930(7) 0.5950(5) 0.0319(17) Uani 1 1 d . . . H4 H 0.1847 0.0193 0.6288 0.038 Uiso 1 1 calc R . . O1 O 0.2591(8) 0.9253(5) -0.1662(4) 0.0274(13) Uani 1 1 d . . . O2 O 0.1677(10) 0.8557(5) -0.2957(4) 0.0358(15) Uani 1 1 d . . . O3 O -0.0798(8) 0.9062(5) -0.1604(4) 0.0291(13) Uani 1 1 d . . . O4 O 0.3730(9) 0.1805(5) -0.1142(4) 0.0284(13) Uani 1 1 d . . . O5 O 0.3397(8) 0.2487(5) 0.0244(3) 0.0264(13) Uani 1 1 d . . . O6 O 0.3137(7) -0.0478(5) 0.0173(3) 0.0223(12) Uani 1 1 d . . . H6A H 0.2969 -0.0552 -0.0357 0.033 Uiso 1 1 d R . . O1W O 0.9109(13) 0.2289(7) 0.8532(5) 0.068(2) Uani 1 1 d . . . H1WA H 1.0320 0.2165 0.8619 0.101 Uiso 1 1 d R . . H1WB H 0.8622 0.1579 0.8681 0.101 Uiso 1 1 d R . . O2W O 0.694(2) 0.4490(12) 0.4400(8) 0.044(3) Uani 0.50 1 d P . . H2WA H 0.7454 0.5191 0.4343 0.066 Uiso 0.50 1 d PR . . H2WB H 0.5813 0.4766 0.4745 0.066 Uiso 0.50 1 d PR . . S1 S 0.1300(3) 0.85497(17) -0.19919(12) 0.0170(4) Uani 1 1 d . . . Tb1 Tb 0.44327(6) 0.05225(4) 0.11431(2) 0.01792(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.013(4) 0.010(3) 0.024(4) 0.002(3) -0.003(3) 0.001(3) C2 0.040(5) 0.025(4) 0.017(4) 0.003(3) -0.012(4) -0.002(4) C3 0.037(5) 0.015(4) 0.022(4) 0.002(3) -0.012(4) -0.001(3) C4 0.024(4) 0.017(4) 0.024(4) 0.001(3) -0.007(4) -0.002(3) C5 0.045(5) 0.024(4) 0.016(4) -0.002(3) 0.000(4) 0.000(4) C6 0.042(5) 0.016(4) 0.019(4) -0.006(3) 0.001(4) -0.001(4) C7 0.031(5) 0.020(4) 0.018(4) 0.005(3) -0.009(4) -0.005(3) C8 0.030(5) 0.018(4) 0.028(5) -0.001(3) -0.006(4) -0.006(3) C9 0.039(5) 0.019(4) 0.039(5) 0.007(4) -0.006(4) -0.007(4) C10 0.028(5) 0.027(4) 0.028(5) 0.007(4) -0.003(4) -0.005(4) C11 0.016(4) 0.025(4) 0.022(4) 0.003(3) -0.005(3) -0.003(3) C12 0.032(5) 0.028(4) 0.014(4) 0.002(3) -0.003(4) -0.005(4) C13 0.037(5) 0.041(5) 0.022(5) -0.008(4) -0.001(4) -0.004(4) C14 0.025(4) 0.022(4) 0.021(4) -0.002(3) -0.003(4) -0.002(3) C15 0.019(4) 0.026(4) 0.015(4) 0.000(3) 0.006(3) -0.006(3) C16 0.042(5) 0.016(4) 0.026(5) -0.006(3) -0.007(4) -0.005(4) C17 0.038(5) 0.014(4) 0.030(5) 0.007(3) -0.008(4) 0.000(4) C18 0.023(4) 0.020(4) 0.029(5) 0.005(3) -0.010(4) -0.005(3) C19 0.014(4) 0.019(4) 0.017(4) 0.000(3) -0.002(3) -0.007(3) C20 0.015(4) 0.020(4) 0.021(4) -0.001(3) -0.004(3) -0.005(3) N1 0.027(4) 0.012(3) 0.024(4) 0.002(3) -0.009(3) -0.003(3) N2 0.021(3) 0.014(3) 0.021(3) 0.000(3) -0.001(3) -0.002(3) N3 0.045(5) 0.027(4) 0.024(4) 0.002(3) -0.002(3) -0.007(3) N4 0.042(4) 0.024(4) 0.026(4) 0.008(3) -0.005(3) -0.005(3) O1 0.022(3) 0.020(3) 0.043(4) -0.001(2) -0.016(3) -0.002(2) O2 0.065(4) 0.019(3) 0.019(3) 0.008(2) -0.005(3) -0.006(3) O3 0.017(3) 0.023(3) 0.044(4) -0.003(3) -0.001(3) 0.000(2) O4 0.046(4) 0.010(3) 0.028(3) -0.001(2) -0.009(3) 0.000(2) O5 0.038(3) 0.013(3) 0.021(3) 0.003(2) -0.005(3) 0.006(2) O6 0.025(3) 0.025(3) 0.019(3) -0.002(2) -0.003(2) -0.010(2) O1W 0.101(6) 0.051(5) 0.062(5) 0.011(4) -0.031(5) -0.032(4) O2W 0.076(10) 0.034(7) 0.023(7) 0.004(5) 0.003(7) -0.030(7) S1 0.0206(10) 0.0121(9) 0.0180(10) 0.0024(7) -0.0044(8) -0.0036(7) Tb1 0.0212(2) 0.01335(19) 0.0184(2) 0.00090(13) -0.00396(15) -0.00252(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.368(10) . ? C1 C2 1.384(11) . ? C1 S1 1.783(7) . ? C2 C3 1.376(10) . ? C2 H2 0.9300 . ? C3 C4 1.394(10) . ? C3 H3 0.9300 . ? C4 C5 1.381(11) . ? C4 C7 1.507(10) . ? C5 C6 1.386(10) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O5 1.246(9) . ? C7 O4 1.272(9) . ? C8 N1 1.330(9) . ? C8 C9 1.379(11) . ? C8 H8 0.9300 . ? C9 C10 1.348(12) . ? C9 H9 0.9300 . ? C10 C11 1.406(10) . ? C10 H10 0.9300 . ? C11 C20 1.403(10) . ? C11 C12 1.433(11) . ? C12 N4 1.356(10) . ? C12 C14 1.372(10) . ? C13 N3 1.320(10) . ? C13 N4 1.340(11) . ? C13 H13 0.9300 . ? C14 N3 1.359(10) . ? C14 C15 1.438(10) . ? C15 C16 1.402(10) . ? C15 C19 1.404(10) . ? C16 C17 1.362(11) . ? C16 H16 0.9300 . ? C17 C18 1.400(11) . ? C17 H17 0.9300 . ? C18 N2 1.325(9) . ? C18 H18 0.9300 . ? C19 N2 1.365(9) . ? C19 C20 1.459(10) . ? C20 N1 1.364(9) . ? N1 Tb1 2.574(6) . ? N2 Tb1 2.577(6) . ? N4 H4 0.8600 . ? O1 S1 1.446(5) . ? O1 Tb1 2.403(5) 2_665 ? O2 S1 1.435(6) . ? O3 S1 1.443(5) . ? O3 Tb1 2.406(5) 2_565 ? O4 Tb1 2.421(5) 2_655 ? O5 Tb1 2.354(5) . ? O6 Tb1 2.294(5) . ? O6 Tb1 2.323(5) 2_655 ? O6 H6A 0.8498 . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? Tb1 O6 2.323(5) 2_655 ? Tb1 O1 2.403(5) 2_665 ? Tb1 O3 2.406(5) 2_565 ? Tb1 O4 2.421(5) 2_655 ? Tb1 Tb1 3.6198(8) 2_655 ? 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 C6 C1 C2 121.5(7) . . ? C6 C1 S1 118.9(6) . . ? C2 C1 S1 119.6(6) . . ? C3 C2 C1 118.7(7) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 121.2(7) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 118.3(7) . . ? C5 C4 C7 120.8(7) . . ? C3 C4 C7 120.8(7) . . ? C4 C5 C6 121.3(7) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.9(7) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? O5 C7 O4 125.5(7) . . ? O5 C7 C4 117.4(7) . . ? O4 C7 C4 117.1(6) . . ? N1 C8 C9 124.0(8) . . ? N1 C8 H8 118.0 . . ? C9 C8 H8 118.0 . . ? C10 C9 C8 119.3(8) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 119.2(7) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C20 C11 C10 118.5(7) . . ? C20 C11 C12 116.3(7) . . ? C10 C11 C12 125.1(7) . . ? N4 C12 C14 105.2(7) . . ? N4 C12 C11 131.3(7) . . ? C14 C12 C11 123.5(7) . . ? N3 C13 N4 113.1(8) . . ? N3 C13 H13 123.5 . . ? N4 C13 H13 123.5 . . ? N3 C14 C12 111.2(7) . . ? N3 C14 C15 128.2(7) . . ? C12 C14 C15 120.7(7) . . ? C16 C15 C19 118.4(7) . . ? C16 C15 C14 123.6(7) . . ? C19 C15 C14 117.9(7) . . ? C17 C16 C15 119.4(7) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 118.4(7) . . ? C16 C17 H17 120.8 . . ? C18 C17 H17 120.8 . . ? N2 C18 C17 124.4(7) . . ? N2 C18 H18 117.8 . . ? C17 C18 H18 117.8 . . ? N2 C19 C15 122.1(6) . . ? N2 C19 C20 117.6(6) . . ? C15 C19 C20 120.3(6) . . ? N1 C20 C11 121.2(7) . . ? N1 C20 C19 117.5(6) . . ? C11 C20 C19 121.3(7) . . ? C8 N1 C20 117.7(6) . . ? C8 N1 Tb1 121.6(5) . . ? C20 N1 Tb1 120.7(4) . . ? C18 N2 C19 117.2(6) . . ? C18 N2 Tb1 122.3(5) . . ? C19 N2 Tb1 120.5(4) . . ? C13 N3 C14 103.6(7) . . ? C13 N4 C12 106.9(7) . . ? C13 N4 H4 126.6 . . ? C12 N4 H4 126.6 . . ? S1 O1 Tb1 155.9(3) . 2_665 ? S1 O3 Tb1 166.0(4) . 2_565 ? C7 O4 Tb1 133.0(5) . 2_655 ? C7 O5 Tb1 133.4(5) . . ? Tb1 O6 Tb1 103.27(19) . 2_655 ? Tb1 O6 H6A 150.0 . . ? Tb1 O6 H6A 53.2 2_655 . ? H1WA O1W H1WB 111.5 . . ? H2WA O2W H2WB 100.3 . . ? O2 S1 O3 113.3(4) . . ? O2 S1 O1 113.1(3) . . ? O3 S1 O1 109.8(3) . . ? O2 S1 C1 107.0(3) . . ? O3 S1 C1 106.0(3) . . ? O1 S1 C1 107.1(3) . . ? O6 Tb1 O6 76.73(19) . 2_655 ? O6 Tb1 O5 82.60(18) . . ? O6 Tb1 O5 73.03(18) 2_655 . ? O6 Tb1 O1 146.80(19) . 2_665 ? O6 Tb1 O1 76.87(18) 2_655 2_665 ? O5 Tb1 O1 108.33(18) . 2_665 ? O6 Tb1 O3 71.66(18) . 2_565 ? O6 Tb1 O3 139.19(19) 2_655 2_565 ? O5 Tb1 O3 77.84(18) . 2_565 ? O1 Tb1 O3 140.52(19) 2_665 2_565 ? O6 Tb1 O4 74.94(18) . 2_655 ? O6 Tb1 O4 76.44(18) 2_655 2_655 ? O5 Tb1 O4 145.44(18) . 2_655 ? O1 Tb1 O4 79.58(18) 2_665 2_655 ? O3 Tb1 O4 117.94(18) 2_565 2_655 ? O6 Tb1 N1 115.09(18) . . ? O6 Tb1 N1 145.42(18) 2_655 . ? O5 Tb1 N1 138.23(18) . . ? O1 Tb1 N1 78.03(19) 2_665 . ? O3 Tb1 N1 73.34(19) 2_565 . ? O4 Tb1 N1 75.93(18) 2_655 . ? O6 Tb1 N2 140.96(18) . . ? O6 Tb1 N2 128.26(18) 2_655 . ? O5 Tb1 N2 78.73(18) . . ? O1 Tb1 N2 72.13(19) 2_665 . ? O3 Tb1 N2 71.05(19) 2_565 . ? O4 Tb1 N2 134.30(18) 2_655 . ? N1 Tb1 N2 63.74(18) . . ? O6 Tb1 Tb1 38.65(12) . 2_655 ? O6 Tb1 Tb1 38.08(12) 2_655 2_655 ? O5 Tb1 Tb1 74.40(13) . 2_655 ? O1 Tb1 Tb1 112.61(14) 2_665 2_655 ? O3 Tb1 Tb1 106.63(14) 2_565 2_655 ? O4 Tb1 Tb1 71.63(13) 2_655 2_655 ? N1 Tb1 Tb1 142.84(13) . 2_655 ? N2 Tb1 Tb1 152.82(13) . 2_655 ? 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 C6 C1 C2 C3 -2.0(12) . . . . ? S1 C1 C2 C3 179.2(6) . . . . ? C1 C2 C3 C4 0.3(12) . . . . ? C2 C3 C4 C5 1.4(12) . . . . ? C2 C3 C4 C7 -178.2(7) . . . . ? C3 C4 C5 C6 -1.5(13) . . . . ? C7 C4 C5 C6 178.1(7) . . . . ? C2 C1 C6 C5 2.0(12) . . . . ? S1 C1 C6 C5 -179.3(6) . . . . ? C4 C5 C6 C1 -0.2(13) . . . . ? C5 C4 C7 O5 5.4(11) . . . . ? C3 C4 C7 O5 -175.0(7) . . . . ? C5 C4 C7 O4 -173.6(8) . . . . ? C3 C4 C7 O4 6.0(11) . . . . ? N1 C8 C9 C10 2.0(13) . . . . ? C8 C9 C10 C11 0.3(13) . . . . ? C9 C10 C11 C20 -2.0(11) . . . . ? C9 C10 C11 C12 178.4(8) . . . . ? C20 C11 C12 N4 -178.1(8) . . . . ? C10 C11 C12 N4 1.5(14) . . . . ? C20 C11 C12 C14 0.7(11) . . . . ? C10 C11 C12 C14 -179.7(8) . . . . ? N4 C12 C14 N3 0.0(9) . . . . ? C11 C12 C14 N3 -179.1(7) . . . . ? N4 C12 C14 C15 179.1(7) . . . . ? C11 C12 C14 C15 0.0(12) . . . . ? N3 C14 C15 C16 -3.6(13) . . . . ? C12 C14 C15 C16 177.5(8) . . . . ? N3 C14 C15 C19 178.2(8) . . . . ? C12 C14 C15 C19 -0.7(11) . . . . ? C19 C15 C16 C17 -0.2(12) . . . . ? C14 C15 C16 C17 -178.4(8) . . . . ? C15 C16 C17 C18 -0.6(12) . . . . ? C16 C17 C18 N2 1.0(12) . . . . ? C16 C15 C19 N2 0.8(11) . . . . ? C14 C15 C19 N2 179.1(6) . . . . ? C16 C15 C19 C20 -177.6(7) . . . . ? C14 C15 C19 C20 0.7(10) . . . . ? C10 C11 C20 N1 1.8(11) . . . . ? C12 C11 C20 N1 -178.6(7) . . . . ? C10 C11 C20 C19 179.7(7) . . . . ? C12 C11 C20 C19 -0.7(10) . . . . ? N2 C19 C20 N1 -0.5(10) . . . . ? C15 C19 C20 N1 178.0(7) . . . . ? N2 C19 C20 C11 -178.5(6) . . . . ? C15 C19 C20 C11 0.0(10) . . . . ? C9 C8 N1 C20 -2.2(11) . . . . ? C9 C8 N1 Tb1 177.1(6) . . . . ? C11 C20 N1 C8 0.3(10) . . . . ? C19 C20 N1 C8 -177.7(6) . . . . ? C11 C20 N1 Tb1 -179.0(5) . . . . ? C19 C20 N1 Tb1 3.0(8) . . . . ? C17 C18 N2 C19 -0.4(11) . . . . ? C17 C18 N2 Tb1 179.8(6) . . . . ? C15 C19 N2 C18 -0.5(10) . . . . ? C20 C19 N2 C18 178.0(6) . . . . ? C15 C19 N2 Tb1 179.3(5) . . . . ? C20 C19 N2 Tb1 -2.2(8) . . . . ? N4 C13 N3 C14 1.5(10) . . . . ? C12 C14 N3 C13 -0.9(9) . . . . ? C15 C14 N3 C13 -179.9(8) . . . . ? N3 C13 N4 C12 -1.5(10) . . . . ? C14 C12 N4 C13 0.9(9) . . . . ? C11 C12 N4 C13 179.8(8) . . . . ? O5 C7 O4 Tb1 -19.0(12) . . . 2_655 ? C4 C7 O4 Tb1 159.9(5) . . . 2_655 ? O4 C7 O5 Tb1 5.3(13) . . . . ? C4 C7 O5 Tb1 -173.5(5) . . . . ? Tb1 O3 S1 O2 58.1(15) 2_565 . . . ? Tb1 O3 S1 O1 -174.4(14) 2_565 . . . ? Tb1 O3 S1 C1 -59.0(15) 2_565 . . . ? Tb1 O1 S1 O2 -89.6(9) 2_665 . . . ? Tb1 O1 S1 O3 142.8(8) 2_665 . . . ? Tb1 O1 S1 C1 28.1(10) 2_665 . . . ? C6 C1 S1 O2 166.1(6) . . . . ? C2 C1 S1 O2 -15.2(7) . . . . ? C6 C1 S1 O3 -72.7(7) . . . . ? C2 C1 S1 O3 106.0(7) . . . . ? C6 C1 S1 O1 44.5(7) . . . . ? C2 C1 S1 O1 -136.7(6) . . . . ? Tb1 O6 Tb1 O6 0.0 2_655 . . 2_655 ? Tb1 O6 Tb1 O5 74.2(2) 2_655 . . . ? Tb1 O6 Tb1 O1 -38.1(4) 2_655 . . 2_665 ? Tb1 O6 Tb1 O3 153.8(2) 2_655 . . 2_565 ? Tb1 O6 Tb1 O4 -79.3(2) 2_655 . . 2_655 ? Tb1 O6 Tb1 N1 -145.45(19) 2_655 . . . ? Tb1 O6 Tb1 N2 136.0(2) 2_655 . . . ? C7 O5 Tb1 O6 -34.3(7) . . . . ? C7 O5 Tb1 O6 44.0(7) . . . 2_655 ? C7 O5 Tb1 O1 113.5(7) . . . 2_665 ? C7 O5 Tb1 O3 -107.1(7) . . . 2_565 ? C7 O5 Tb1 O4 15.1(9) . . . 2_655 ? C7 O5 Tb1 N1 -154.1(6) . . . . ? C7 O5 Tb1 N2 -179.9(7) . . . . ? C7 O5 Tb1 Tb1 4.3(7) . . . 2_655 ? C8 N1 Tb1 O6 41.4(6) . . . . ? C20 N1 Tb1 O6 -139.3(5) . . . . ? C8 N1 Tb1 O6 -62.1(7) . . . 2_655 ? C20 N1 Tb1 O6 117.2(5) . . . 2_655 ? C8 N1 Tb1 O5 149.5(5) . . . . ? C20 N1 Tb1 O5 -31.2(7) . . . . ? C8 N1 Tb1 O1 -106.3(6) . . . 2_665 ? C20 N1 Tb1 O1 73.0(5) . . . 2_665 ? C8 N1 Tb1 O3 101.2(6) . . . 2_565 ? C20 N1 Tb1 O3 -79.5(5) . . . 2_565 ? C8 N1 Tb1 O4 -24.2(6) . . . 2_655 ? C20 N1 Tb1 O4 155.1(6) . . . 2_655 ? C8 N1 Tb1 N2 177.9(6) . . . . ? C20 N1 Tb1 N2 -2.8(5) . . . . ? C8 N1 Tb1 Tb1 5.5(7) . . . 2_655 ? C20 N1 Tb1 Tb1 -175.3(4) . . . 2_655 ? C18 N2 Tb1 O6 -79.4(6) . . . . ? C19 N2 Tb1 O6 100.7(5) . . . . ? C18 N2 Tb1 O6 41.1(6) . . . 2_655 ? C19 N2 Tb1 O6 -138.7(5) . . . 2_655 ? C18 N2 Tb1 O5 -16.5(5) . . . . ? C19 N2 Tb1 O5 163.7(5) . . . . ? C18 N2 Tb1 O1 97.2(6) . . . 2_665 ? C19 N2 Tb1 O1 -82.6(5) . . . 2_665 ? C18 N2 Tb1 O3 -97.3(6) . . . 2_565 ? C19 N2 Tb1 O3 82.8(5) . . . 2_565 ? C18 N2 Tb1 O4 151.7(5) . . . 2_655 ? C19 N2 Tb1 O4 -28.1(6) . . . 2_655 ? C18 N2 Tb1 N1 -177.6(6) . . . . ? C19 N2 Tb1 N1 2.6(5) . . . . ? C18 N2 Tb1 Tb1 -7.7(7) . . . 2_655 ? C19 N2 Tb1 Tb1 172.5(4) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.007 _refine_diff_density_min -1.249 _refine_diff_density_rms 0.183 _database_code_depnum_ccdc_archive 'CCDC 956200'