# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Zhao Wang' _publ_contact_author_email ZXWANG@SHU.EDU.CN _publ_section_title ; 2D and 3D lanthanide coordination polymers constructed from benzimidazole-5,6-dicarboxylic acid and sulfate bridged secondary building units ; loop_ _publ_author_name 'Zhao Wang' 'Ming-Xing Li' 'Hong-Jiang Liu' 'Min Shao' 'Qiong-Fang Wu' ; Hong-Ping Xiao ; # Attachment 'Dy.cif' data_Dy _database_code_depnum_ccdc_archive 'CCDC 734649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C18 H8 Dy2 N4 O12 S), H4 O2' _chemical_formula_sum 'C36 H20 Dy4 N8 O26 S2' _chemical_formula_weight 1694.72 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' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5378(8) _cell_length_b 6.6828(5) _cell_length_c 16.1310(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.7490(10) _cell_angle_gamma 90.00 _cell_volume 1021.05(14) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2372 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 25.34 _exptl_crystal_description cubic _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.756 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 7.452 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.272 _exptl_absorpt_correction_T_max 0.409 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 area-detector diffractometer' _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 5263 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1876 _reflns_number_gt 1742 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material 'SHELXTL(Bruker, 2002)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0212P)^2^+39.3783P] 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 1876 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.168 _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 0.59113(5) 0.42091(7) 0.39873(3) 0.01187(17) Uani 1 1 d . . . S1 S 0.4075(6) 0.0797(8) 0.5221(3) 0.0156(10) Uani 0.50 1 d P . . O1 O 0.7974(10) 0.381(2) 0.4950(5) 0.063(4) Uani 1 1 d . . . O2 O 0.6229(9) 0.4795(18) 0.5544(5) 0.040(3) Uani 1 1 d . . . O3 O 0.5678(8) 0.5305(14) 0.7111(5) 0.026(2) Uani 1 1 d . . . O4 O 0.6480(9) 0.3429(14) 0.8178(6) 0.034(2) Uani 1 1 d . . . O5 O 0.4955(19) 0.130(3) 0.4491(11) 0.031(4) Uani 0.50 1 d P . . O6 O 0.3995(9) 0.2291(13) 0.5857(5) 0.0254(18) Uani 1 1 d . . . O7 O 0.2585(19) 0.038(3) 0.4961(11) 0.037(5) Uani 0.50 1 d P . . O8 O 0.060(3) 0.026(6) 0.4957(15) 0.083(10) Uani 0.50 1 d P . . H8A H 0.0106 0.1137 0.4674 0.125 Uiso 0.50 1 d PR . . H8B H 0.0242 -0.0894 0.4846 0.125 Uiso 0.50 1 d PR . . N2 N 1.1790(10) 0.4386(16) 0.8301(6) 0.023(2) Uani 1 1 d . . . H2 H 1.1874 0.4351 0.8837 0.027 Uiso 1 1 calc R . . N1 N 1.2406(9) 0.4539(15) 0.6995(6) 0.019(2) Uani 1 1 d . . . C1 C 0.7489(11) 0.4321(17) 0.5607(7) 0.019(2) Uani 1 1 d . . . C2 C 0.8485(11) 0.4381(17) 0.6406(6) 0.016(2) Uani 1 1 d . . . C3 C 0.9889(11) 0.4414(17) 0.6274(7) 0.018(2) Uani 1 1 d . . . H3 H 1.0136 0.4421 0.5733 0.021 Uiso 1 1 calc R . . C4 C 1.0944(11) 0.4436(16) 0.6960(6) 0.015(2) Uani 1 1 d . . . C5 C 1.0550(11) 0.4342(17) 0.7758(6) 0.018(2) Uani 1 1 d . . . C6 C 0.9155(11) 0.4295(18) 0.7912(7) 0.019(2) Uani 1 1 d . . . H6 H 0.8922 0.4242 0.8456 0.022 Uiso 1 1 calc R . . C7 C 0.8119(11) 0.4328(17) 0.7244(6) 0.015(2) Uani 1 1 d . . . C8 C 0.6639(11) 0.4320(17) 0.7510(6) 0.017(2) Uani 1 1 d . . . C9 C 1.2870(11) 0.4499(18) 0.7791(7) 0.020(2) Uani 1 1 d . . . H9 H 1.3822 0.4541 0.7996 0.024 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 0.0110(3) 0.0155(3) 0.0092(3) -0.0008(2) 0.00173(17) 0.0006(2) S1 0.023(3) 0.014(3) 0.011(2) 0.002(2) 0.008(2) -0.002(2) O1 0.021(5) 0.153(13) 0.014(4) -0.019(6) -0.001(4) 0.027(7) O2 0.018(4) 0.086(8) 0.017(4) -0.010(5) -0.003(3) 0.016(5) O3 0.013(4) 0.051(6) 0.015(4) 0.002(4) -0.001(3) 0.003(4) O4 0.028(5) 0.038(5) 0.041(5) 0.023(4) 0.020(4) 0.012(4) O5 0.034(10) 0.030(10) 0.030(9) 0.002(8) 0.007(8) -0.004(8) O6 0.026(4) 0.023(4) 0.026(4) -0.004(4) 0.003(4) -0.001(4) O7 0.028(9) 0.054(13) 0.029(9) 0.005(9) 0.002(8) -0.012(9) O8 0.069(17) 0.15(3) 0.034(12) -0.015(16) 0.000(14) 0.04(2) N2 0.017(5) 0.031(6) 0.021(5) 0.002(4) 0.009(4) 0.002(4) N1 0.014(4) 0.028(5) 0.017(5) 0.004(4) 0.005(4) 0.002(4) C1 0.017(5) 0.020(6) 0.019(5) 0.001(5) 0.000(4) 0.003(5) C2 0.015(5) 0.023(6) 0.011(5) -0.001(4) 0.005(4) 0.002(4) C3 0.016(5) 0.023(6) 0.015(5) 0.004(5) 0.007(4) -0.001(5) C4 0.012(5) 0.017(5) 0.015(5) 0.000(4) 0.001(4) -0.005(4) C5 0.018(5) 0.022(6) 0.013(5) 0.000(5) 0.001(4) 0.003(5) C6 0.020(5) 0.022(6) 0.014(5) -0.001(5) -0.001(4) 0.000(5) C7 0.017(5) 0.017(5) 0.012(5) 0.003(4) 0.004(4) -0.001(4) C8 0.016(5) 0.020(6) 0.015(5) -0.001(5) 0.000(4) -0.001(5) C9 0.011(5) 0.031(7) 0.019(5) 0.005(5) 0.003(4) -0.004(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 Dy1 O3 2.216(7) 3_666 ? Dy1 O4 2.296(8) 4_565 ? Dy1 O5 2.335(18) . ? Dy1 O6 2.353(8) 3_666 ? Dy1 O2 2.355(8) 3_666 ? Dy1 O1 2.374(9) . ? Dy1 O2 2.524(8) . ? Dy1 N1 2.526(9) 3_766 ? Dy1 C1 2.858(11) . ? S1 O6 1.440(10) . ? S1 O7 1.460(18) . ? S1 O5 1.561(18) . ? S1 O5 1.711(19) 3_656 ? S1 S1 2.248(11) 3_656 ? O1 C1 1.252(14) . ? O2 C1 1.235(13) . ? O2 Dy1 2.355(8) 3_666 ? O3 C8 1.244(13) . ? O3 Dy1 2.216(7) 3_666 ? O4 C8 1.257(14) . ? O4 Dy1 2.296(8) 4_566 ? O5 S1 1.711(19) 3_656 ? O6 Dy1 2.353(8) 3_666 ? O8 O8 1.21(5) 3_556 ? O8 H8A 0.8500 . ? O8 H8B 0.8500 . ? N2 C5 1.386(14) . ? N2 C9 1.394(14) . ? N2 H2 0.8600 . ? N1 C9 1.308(14) . ? N1 C4 1.391(13) . ? N1 Dy1 2.526(9) 3_766 ? C1 C2 1.510(14) . ? C2 C3 1.381(14) . ? C2 C7 1.435(14) . ? C3 C4 1.405(14) . ? C3 H3 0.9300 . ? C4 C5 1.384(15) . ? C5 C6 1.383(15) . ? C6 C7 1.374(14) . ? C6 H6 0.9300 . ? C7 C8 1.522(14) . ? C9 H9 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 O3 Dy1 O4 81.0(3) 3_666 4_565 ? O3 Dy1 O5 98.2(5) 3_666 . ? O4 Dy1 O5 71.7(5) 4_565 . ? O3 Dy1 O6 87.3(3) 3_666 3_666 ? O4 Dy1 O6 144.6(3) 4_565 3_666 ? O5 Dy1 O6 143.4(5) . 3_666 ? O3 Dy1 O2 71.2(3) 3_666 3_666 ? O4 Dy1 O2 132.2(3) 4_565 3_666 ? O5 Dy1 O2 74.6(5) . 3_666 ? O6 Dy1 O2 73.0(4) 3_666 3_666 ? O3 Dy1 O1 167.4(3) 3_666 . ? O4 Dy1 O1 93.0(4) 4_565 . ? O5 Dy1 O1 90.4(6) . . ? O6 Dy1 O1 91.3(4) 3_666 . ? O2 Dy1 O1 120.3(3) 3_666 . ? O3 Dy1 O2 139.8(3) 3_666 . ? O4 Dy1 O2 132.5(4) 4_565 . ? O5 Dy1 O2 77.8(5) . . ? O6 Dy1 O2 75.0(3) 3_666 . ? O2 Dy1 O2 69.1(3) 3_666 . ? O1 Dy1 O2 51.2(3) . . ? O3 Dy1 N1 82.8(3) 3_666 3_766 ? O4 Dy1 N1 71.8(3) 4_565 3_766 ? O5 Dy1 N1 142.9(5) . 3_766 ? O6 Dy1 N1 73.7(3) 3_666 3_766 ? O2 Dy1 N1 138.3(3) 3_666 3_766 ? O1 Dy1 N1 84.8(3) . 3_766 ? O2 Dy1 N1 124.2(3) . 3_766 ? O3 Dy1 C1 164.6(3) 3_666 . ? O4 Dy1 C1 113.9(3) 4_565 . ? O5 Dy1 C1 83.6(5) . . ? O6 Dy1 C1 82.4(3) 3_666 . ? O2 Dy1 C1 94.7(3) 3_666 . ? O1 Dy1 C1 25.6(3) . . ? O2 Dy1 C1 25.6(3) . . ? N1 Dy1 C1 105.0(3) 3_766 . ? O6 S1 O7 101.8(9) . . ? O6 S1 O5 117.8(8) . . ? O7 S1 O5 114.5(10) . . ? O6 S1 O5 116.5(8) . 3_656 ? O7 S1 O5 113.6(11) . 3_656 ? O5 S1 O5 93.3(9) . 3_656 ? O6 S1 S1 131.6(6) . 3_656 ? O7 S1 S1 126.4(9) . 3_656 ? O5 S1 S1 49.5(7) . 3_656 ? O5 S1 S1 43.9(6) 3_656 3_656 ? C1 O1 Dy1 99.4(7) . . ? C1 O2 Dy1 156.6(8) . 3_666 ? C1 O2 Dy1 92.5(7) . . ? Dy1 O2 Dy1 110.9(3) 3_666 . ? C8 O3 Dy1 152.1(8) . 3_666 ? C8 O4 Dy1 155.8(9) . 4_566 ? S1 O5 S1 86.7(9) . 3_656 ? S1 O5 Dy1 135.1(11) . . ? S1 O5 Dy1 123.7(9) 3_656 . ? S1 O6 Dy1 139.6(5) . 3_666 ? O8 O8 H8A 78.1 3_556 . ? O8 O8 H8B 54.1 3_556 . ? H8A O8 H8B 109.5 . . ? C5 N2 C9 105.2(9) . . ? C5 N2 H2 127.4 . . ? C9 N2 H2 127.4 . . ? C9 N1 C4 105.1(9) . . ? C9 N1 Dy1 117.1(7) . 3_766 ? C4 N1 Dy1 134.3(7) . 3_766 ? O2 C1 O1 116.9(10) . . ? O2 C1 C2 124.9(10) . . ? O1 C1 C2 118.2(9) . . ? O2 C1 Dy1 61.9(6) . . ? O1 C1 Dy1 55.0(6) . . ? C2 C1 Dy1 172.9(7) . . ? C3 C2 C7 119.6(9) . . ? C3 C2 C1 113.1(9) . . ? C7 C2 C1 127.3(9) . . ? C2 C3 C4 119.7(9) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 N1 110.2(9) . . ? C5 C4 C3 119.0(9) . . ? N1 C4 C3 130.9(9) . . ? C6 C5 C4 122.7(10) . . ? C6 C5 N2 130.8(10) . . ? C4 C5 N2 106.4(9) . . ? C7 C6 C5 118.5(10) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C6 C7 C2 120.4(10) . . ? C6 C7 C8 112.6(9) . . ? C2 C7 C8 127.0(9) . . ? O3 C8 O4 122.6(10) . . ? O3 C8 C7 120.2(10) . . ? O4 C8 C7 116.9(9) . . ? N1 C9 N2 113.1(9) . . ? N1 C9 H9 123.4 . . ? N2 C9 H9 123.4 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 3.906 _refine_diff_density_min -3.471 _refine_diff_density_rms 0.254 # Attachment 'Er.cif' data_Er _database_code_depnum_ccdc_archive 'CCDC 734650' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C18 H8 N4 Er2 O12 S ), H4 O2' _chemical_formula_sum 'C36 H20 Er4 N8 O26 S2' _chemical_formula_weight 1713.76 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5378(8) _cell_length_b 6.6828(5) _cell_length_c 16.1310(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.7490(10) _cell_angle_gamma 90.00 _cell_volume 1021.05(14) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2372 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 25.34 _exptl_crystal_description block _exptl_crystal_colour Pink _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.787 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 8.353 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.162 _exptl_absorpt_correction_T_max 0.242 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 area-detector diffractometer' _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 4829 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.10 _reflns_number_total 1810 _reflns_number_gt 1676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material 'SHELXTL(Bruker, 2002)' _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^)+(0.0562P)^2^+34.2626P] 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 1810 _refine_ls_number_parameters 190 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.182 _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 0.59066(5) 0.42155(8) 0.39863(3) 0.0098(2) Uani 1 1 d U . . S1 S 0.4066(7) 0.0815(9) 0.5218(4) 0.0158(13) Uani 0.50 1 d P . . O1 O 0.7973(11) 0.378(2) 0.4942(6) 0.049(4) Uani 1 1 d . . . O2 O 0.6214(11) 0.4790(17) 0.5531(6) 0.031(2) Uani 1 1 d U . . O3 O 0.5653(9) 0.5300(15) 0.7111(6) 0.0206(19) Uani 1 1 d U . . O4 O 0.6466(9) 0.3409(17) 0.8172(6) 0.030(2) Uani 1 1 d . . . O5 O 0.4992(19) 0.132(3) 0.4502(11) 0.023(4) Uani 0.50 1 d PU . . O6 O 0.3998(17) 0.2316(18) 0.5862(7) 0.057(4) Uani 1 1 d . . . O7 O 0.257(2) 0.046(3) 0.4963(12) 0.028(5) Uani 0.50 1 d P . . O8 O 0.060(3) 0.024(6) 0.4953(16) 0.073(10) Uani 0.50 1 d P . . H8A H 0.0114 0.1116 0.4670 0.109 Uiso 0.50 1 d PR . . H8B H 0.0250 -0.0915 0.4842 0.109 Uiso 0.50 1 d PR . . N2 N 1.1783(11) 0.4359(17) 0.8283(7) 0.021(3) Uani 1 1 d . . . H2 H 1.1860 0.4333 0.8819 0.025 Uiso 1 1 calc R . . N1 N 1.2421(10) 0.4529(17) 0.6985(6) 0.016(2) Uani 1 1 d . . . C1 C 0.7484(12) 0.4313(18) 0.5603(7) 0.012(2) Uani 1 1 d U . . C2 C 0.8482(13) 0.4387(19) 0.6394(8) 0.016(3) Uani 1 1 d . . . C3 C 0.9886(12) 0.4398(19) 0.6256(8) 0.015(3) Uani 1 1 d . . . H3 H 1.0132 0.4386 0.5715 0.018 Uiso 1 1 calc R . . C4 C 1.0943(12) 0.4429(18) 0.6946(8) 0.012(2) Uani 1 1 d . . . C5 C 1.0551(13) 0.4310(18) 0.7749(8) 0.015(3) Uani 1 1 d . . . C6 C 0.9143(13) 0.4262(19) 0.7911(8) 0.017(3) Uani 1 1 d . . . H6 H 0.8910 0.4205 0.8454 0.020 Uiso 1 1 calc R . . C7 C 0.8115(13) 0.4301(18) 0.7239(8) 0.014(3) Uani 1 1 d . . . C8 C 0.6646(12) 0.4287(17) 0.7515(7) 0.012(2) Uani 1 1 d . . . C9 C 1.2888(13) 0.4457(19) 0.7785(9) 0.019(3) Uani 1 1 d . . . H9 H 1.3839 0.4470 0.7995 0.023 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 0.0048(3) 0.0124(4) 0.0114(3) -0.00053(19) -0.0027(2) 0.00041(19) S1 0.016(3) 0.019(3) 0.012(3) 0.003(2) 0.002(2) 0.000(2) O1 0.018(5) 0.112(11) 0.015(5) -0.015(6) -0.007(4) 0.024(6) O2 0.031(2) 0.032(2) 0.031(2) -0.0004(10) 0.0032(11) 0.0005(10) O3 0.020(2) 0.021(2) 0.020(2) -0.0021(10) 0.0016(10) 0.0002(10) O4 0.017(5) 0.037(6) 0.039(6) 0.021(5) 0.012(4) 0.010(5) O5 0.024(4) 0.023(4) 0.022(4) 0.0033(11) 0.0026(11) -0.0012(11) O6 0.128(13) 0.019(6) 0.028(6) -0.005(5) 0.029(7) -0.002(7) O7 0.023(10) 0.035(12) 0.021(10) 0.011(8) -0.008(8) -0.016(9) O8 0.046(14) 0.14(3) 0.033(14) -0.028(17) 0.001(12) 0.04(2) N2 0.012(5) 0.033(7) 0.017(6) -0.002(5) 0.001(4) 0.003(5) N1 0.009(5) 0.025(6) 0.012(5) 0.005(4) -0.002(4) 0.002(4) C1 0.007(4) 0.014(6) 0.012(5) 0.000(4) -0.005(4) 0.000(4) C2 0.012(6) 0.019(7) 0.017(6) 0.000(5) 0.005(5) 0.001(5) C3 0.007(5) 0.022(7) 0.015(6) 0.001(5) -0.004(5) 0.000(5) C4 0.006(5) 0.009(6) 0.020(6) 0.003(5) -0.001(5) -0.002(4) C5 0.009(6) 0.012(7) 0.022(7) 0.002(5) -0.005(5) 0.004(5) C6 0.009(6) 0.022(8) 0.019(7) -0.001(5) -0.002(5) 0.004(5) C7 0.012(6) 0.017(7) 0.013(6) 0.009(5) 0.003(5) 0.003(5) C8 0.006(5) 0.011(6) 0.017(6) 0.002(5) -0.003(5) 0.003(4) C9 0.005(5) 0.017(7) 0.036(8) 0.008(6) 0.001(5) 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 Er1 O3 2.198(9) 3_666 ? Er1 O4 2.291(10) 4_565 ? Er1 O5 2.318(19) . ? Er1 O6 2.332(12) 3_666 ? Er1 O2 2.348(10) 3_666 ? Er1 O1 2.374(10) . ? Er1 O2 2.504(10) . ? Er1 N1 2.508(10) 3_766 ? Er1 C1 2.855(11) . ? S1 O6 1.450(12) . ? S1 O7 1.458(19) . ? S1 O5 1.572(19) . ? S1 O5 1.72(2) 3_656 ? S1 S1 2.270(12) 3_656 ? O1 C1 1.264(16) . ? O2 C1 1.244(15) . ? O2 Er1 2.348(10) 3_666 ? O3 C8 1.278(15) . ? O3 Er1 2.198(9) 3_666 ? O4 C8 1.242(15) . ? O4 Er1 2.291(10) 4_566 ? O5 S1 1.72(2) 3_656 ? O6 Er1 2.332(12) 3_666 ? O8 O8 1.22(6) 3_556 ? O8 H8A 0.8500 . ? O8 H8B 0.8500 . ? N2 C5 1.373(16) . ? N2 C9 1.400(17) . ? N2 H2 0.8600 . ? N1 C9 1.316(17) . ? N1 C4 1.405(15) . ? N1 Er1 2.508(10) 3_766 ? C1 C2 1.499(17) . ? C2 C3 1.384(17) . ? C2 C7 1.448(17) . ? C3 C4 1.411(17) . ? C3 H3 0.9300 . ? C4 C5 1.391(18) . ? C5 C6 1.399(17) . ? C6 C7 1.373(18) . ? C6 H6 0.9300 . ? C7 C8 1.519(16) . ? C9 H9 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 O3 Er1 O4 80.4(4) 3_666 4_565 ? O3 Er1 O5 99.5(5) 3_666 . ? O4 Er1 O5 71.9(5) 4_565 . ? O3 Er1 O6 87.3(4) 3_666 3_666 ? O4 Er1 O6 144.3(4) 4_565 3_666 ? O5 Er1 O6 143.6(5) . 3_666 ? O3 Er1 O2 72.4(3) 3_666 3_666 ? O4 Er1 O2 132.4(3) 4_565 3_666 ? O5 Er1 O2 75.1(5) . 3_666 ? O6 Er1 O2 73.0(5) 3_666 3_666 ? O3 Er1 O1 166.7(4) 3_666 . ? O4 Er1 O1 92.7(4) 4_565 . ? O5 Er1 O1 89.1(6) . . ? O6 Er1 O1 91.9(5) 3_666 . ? O2 Er1 O1 120.1(3) 3_666 . ? O3 Er1 O2 140.1(3) 3_666 . ? O4 Er1 O2 132.8(4) 4_565 . ? O5 Er1 O2 77.1(5) . . ? O6 Er1 O2 75.2(4) 3_666 . ? O2 Er1 O2 68.4(4) 3_666 . ? O1 Er1 O2 51.7(3) . . ? O3 Er1 N1 82.4(3) 3_666 3_766 ? O4 Er1 N1 71.9(4) 4_565 3_766 ? O5 Er1 N1 142.9(5) . 3_766 ? O6 Er1 N1 73.4(4) 3_666 3_766 ? O2 Er1 N1 138.5(4) 3_666 3_766 ? O1 Er1 N1 84.6(4) . 3_766 ? O2 Er1 N1 124.2(3) . 3_766 ? O3 Er1 C1 165.1(3) 3_666 . ? O4 Er1 C1 114.1(4) 4_565 . ? O5 Er1 C1 82.6(5) . . ? O6 Er1 C1 82.6(4) 3_666 . ? O2 Er1 C1 94.2(3) 3_666 . ? O1 Er1 C1 25.9(3) . . ? O2 Er1 C1 25.8(3) . . ? N1 Er1 C1 104.9(3) 3_766 . ? O6 S1 O7 101.0(12) . . ? O6 S1 O5 117.0(10) . . ? O7 S1 O5 116.4(11) . . ? O6 S1 O5 116.9(9) . 3_656 ? O7 S1 O5 113.7(11) . 3_656 ? O5 S1 O5 92.8(10) . 3_656 ? O6 S1 S1 131.0(8) . 3_656 ? O7 S1 S1 127.7(10) . 3_656 ? O5 S1 S1 49.1(7) . 3_656 ? O5 S1 S1 43.7(6) 3_656 3_656 ? C1 O1 Er1 98.8(7) . . ? C1 O2 Er1 155.3(9) . 3_666 ? C1 O2 Er1 93.1(8) . . ? Er1 O2 Er1 111.6(4) 3_666 . ? C8 O3 Er1 151.5(8) . 3_666 ? C8 O4 Er1 156.4(10) . 4_566 ? S1 O5 S1 87.2(10) . 3_656 ? S1 O5 Er1 135.3(11) . . ? S1 O5 Er1 125.5(10) 3_656 . ? S1 O6 Er1 139.3(7) . 3_666 ? O8 O8 H8A 77.2 3_556 . ? O8 O8 H8B 55.6 3_556 . ? H8A O8 H8B 109.5 . . ? C5 N2 C9 106.7(11) . . ? C5 N2 H2 126.6 . . ? C9 N2 H2 126.6 . . ? C9 N1 C4 105.3(10) . . ? C9 N1 Er1 117.2(8) . 3_766 ? C4 N1 Er1 134.2(8) . 3_766 ? O2 C1 O1 116.4(11) . . ? O2 C1 C2 125.8(11) . . ? O1 C1 C2 117.8(10) . . ? O2 C1 Er1 61.1(7) . . ? O1 C1 Er1 55.2(6) . . ? C2 C1 Er1 172.5(8) . . ? C3 C2 C7 119.7(11) . . ? C3 C2 C1 113.2(10) . . ? C7 C2 C1 126.9(11) . . ? C2 C3 C4 119.3(11) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 N1 109.8(10) . . ? C5 C4 C3 119.2(11) . . ? N1 C4 C3 131.0(11) . . ? N2 C5 C4 106.2(11) . . ? N2 C5 C6 130.8(12) . . ? C4 C5 C6 123.0(12) . . ? C7 C6 C5 117.7(12) . . ? C7 C6 H6 121.2 . . ? C5 C6 H6 121.2 . . ? C6 C7 C2 121.0(11) . . ? C6 C7 C8 111.5(10) . . ? C2 C7 C8 127.5(11) . . ? O4 C8 O3 121.1(11) . . ? O4 C8 C7 118.6(10) . . ? O3 C8 C7 120.1(10) . . ? N1 C9 N2 111.9(10) . . ? N1 C9 H9 124.1 . . ? N2 C9 H9 124.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 3.712 _refine_diff_density_min -2.516 _refine_diff_density_rms 0.335 # Attachment 'Eu.cif' data_Eu _database_code_depnum_ccdc_archive 'CCDC 734651' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C18 H8 Eu2 N4 O12 S), H4 O2' _chemical_formula_sum 'C36 H20 Eu4 N8 O26 S2' _chemical_formula_weight 1652.56 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5378(8) _cell_length_b 6.6828(5) _cell_length_c 16.1310(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.7490(10) _cell_angle_gamma 90.00 _cell_volume 1021.05(14) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2372 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 25.34 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 6.277 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.249 _exptl_absorpt_correction_T_max 0.390 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 area-detector diffractometer' _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 5294 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1878 _reflns_number_gt 1832 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material 'SHELXTL(Bruker, 2002)' _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^)+(0.0001P)^2^+56.0788P] 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 1878 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _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 0.59264(6) 0.41862(9) 0.39933(3) 0.01118(19) Uani 1 1 d . . . S1 S 0.4090(6) 0.0747(9) 0.5230(3) 0.0158(11) Uani 0.50 1 d P . . O1 O 0.7987(13) 0.3868(19) 0.4987(7) 0.051(3) Uani 1 1 d . . . O2 O 0.6248(10) 0.473(2) 0.5571(6) 0.047(4) Uani 1 1 d . . . O3 O 0.5690(9) 0.5348(17) 0.7119(5) 0.028(2) Uani 1 1 d . . . O4 O 0.6490(10) 0.3503(16) 0.8183(6) 0.033(2) Uani 1 1 d . . . O5 O 0.4878(19) 0.127(2) 0.4487(11) 0.022(4) Uani 0.50 1 d P . . O6 O 0.3923(12) 0.2258(18) 0.5835(6) 0.040(3) Uani 1 1 d . . . O7 O 0.262(2) 0.017(4) 0.4992(12) 0.038(5) Uani 0.50 1 d P . . O8 O 0.053(3) 0.019(7) 0.4936(16) 0.086(12) Uani 0.50 1 d P . . H8A H 0.0040 0.1072 0.4653 0.130 Uiso 0.50 1 d PR . . H8B H 0.0176 -0.0959 0.4825 0.130 Uiso 0.50 1 d PR . . N2 N 1.1795(10) 0.4445(17) 0.8310(6) 0.019(2) Uani 1 1 d . . . H2 H 1.1877 0.4409 0.8846 0.023 Uiso 1 1 calc R . . N1 N 1.2396(10) 0.4576(16) 0.7012(6) 0.018(2) Uani 1 1 d . . . C1 C 0.7497(12) 0.4354(19) 0.5630(7) 0.017(2) Uani 1 1 d . . . C2 C 0.8482(12) 0.4434(19) 0.6422(7) 0.015(2) Uani 1 1 d . . . C3 C 0.9897(12) 0.445(2) 0.6302(7) 0.018(3) Uani 1 1 d . . . H3 H 1.0151 0.4443 0.5763 0.022 Uiso 1 1 calc R . . C4 C 1.0933(12) 0.4488(18) 0.6976(7) 0.014(2) Uani 1 1 d . . . C5 C 1.0555(12) 0.4408(19) 0.7774(7) 0.018(2) Uani 1 1 d . . . C6 C 0.9161(13) 0.4348(19) 0.7921(7) 0.019(2) Uani 1 1 d . . . H6 H 0.8929 0.4283 0.8464 0.022 Uiso 1 1 calc R . . C7 C 0.8135(12) 0.4386(18) 0.7266(7) 0.015(2) Uani 1 1 d . . . C8 C 0.6649(12) 0.4387(19) 0.7515(7) 0.016(2) Uani 1 1 d . . . C9 C 1.2876(12) 0.4552(19) 0.7812(7) 0.018(2) Uani 1 1 d . . . H9 H 1.3828 0.4601 0.8017 0.022 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.0096(3) 0.0150(3) 0.0090(3) -0.0013(2) 0.00164(19) 0.0003(2) S1 0.022(3) 0.015(3) 0.012(3) 0.000(2) 0.007(2) -0.004(2) O1 0.059(8) 0.051(8) 0.042(7) -0.027(6) -0.003(6) 0.001(6) O2 0.014(4) 0.109(11) 0.017(5) -0.018(6) -0.003(4) 0.021(6) O3 0.014(4) 0.056(7) 0.014(4) 0.004(4) 0.004(3) 0.006(4) O4 0.030(5) 0.034(6) 0.041(6) 0.021(5) 0.024(5) 0.013(4) O5 0.029(9) 0.006(8) 0.030(10) 0.003(7) 0.003(8) -0.001(7) O6 0.053(7) 0.044(7) 0.023(5) -0.010(5) 0.003(5) -0.001(6) O7 0.024(10) 0.066(16) 0.024(10) -0.008(10) 0.000(8) -0.015(10) O8 0.059(18) 0.17(4) 0.029(13) -0.016(18) -0.004(14) 0.04(3) N2 0.015(5) 0.030(6) 0.013(5) -0.003(4) 0.006(4) 0.001(5) N1 0.013(5) 0.027(6) 0.014(5) 0.003(4) 0.005(4) -0.003(4) C1 0.016(6) 0.018(6) 0.018(6) 0.000(5) 0.003(5) 0.003(5) C2 0.014(5) 0.021(6) 0.011(5) -0.001(5) 0.001(4) -0.003(5) C3 0.015(6) 0.028(7) 0.013(5) 0.005(5) 0.006(4) -0.002(5) C4 0.014(5) 0.013(6) 0.017(6) 0.000(4) 0.003(4) -0.005(5) C5 0.016(6) 0.021(6) 0.016(6) 0.003(5) 0.000(4) 0.006(5) C6 0.020(6) 0.020(6) 0.016(6) -0.001(5) 0.004(5) -0.001(5) C7 0.014(5) 0.017(6) 0.015(5) 0.003(5) 0.007(4) 0.000(5) C8 0.015(6) 0.018(6) 0.014(5) -0.005(5) 0.004(4) -0.006(5) C9 0.010(5) 0.023(7) 0.022(6) 0.002(5) 0.003(4) -0.006(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O3 2.245(8) 3_666 ? Eu1 O4 2.322(9) 4_565 ? Eu1 O5 2.370(16) . ? Eu1 O2 2.379(9) 3_666 ? Eu1 O6 2.394(12) 3_666 ? Eu1 O1 2.395(12) . ? Eu1 N1 2.546(9) 3_766 ? Eu1 O2 2.554(9) . ? Eu1 C1 2.880(12) . ? Eu1 S1 3.528(6) 3_656 ? Eu1 Eu1 4.0253(11) 3_666 ? S1 O6 1.426(12) . ? S1 O7 1.465(19) . ? S1 O5 1.528(18) . ? S1 O5 1.699(17) 3_656 ? S1 S1 2.205(12) 3_656 ? S1 Eu1 3.528(6) 3_656 ? O1 C1 1.231(16) . ? O2 C1 1.210(15) . ? O2 Eu1 2.379(9) 3_666 ? O3 C8 1.233(15) . ? O3 Eu1 2.245(8) 3_666 ? O4 C8 1.254(15) . ? O4 Eu1 2.322(9) 4_566 ? O5 S1 1.699(17) 3_656 ? O6 Eu1 2.394(12) 3_666 ? O8 O8 1.08(6) 3_556 ? O8 H8A 0.8500 . ? O8 H8B 0.8500 . ? N2 C5 1.380(15) . ? N2 C9 1.382(15) . ? N2 H2 0.8600 . ? N1 C9 1.318(15) . ? N1 C4 1.392(14) . ? N1 Eu1 2.546(9) 3_766 ? C1 C2 1.495(16) . ? C2 C3 1.386(16) . ? C2 C7 1.439(15) . ? C3 C4 1.380(16) . ? C3 H3 0.9300 . ? C4 C5 1.378(16) . ? C5 C6 1.378(17) . ? C6 C7 1.353(16) . ? C6 H6 0.9300 . ? C7 C8 1.518(15) . ? C9 H9 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 O3 Eu1 O4 80.8(4) 3_666 4_565 ? O3 Eu1 O5 96.1(5) 3_666 . ? O4 Eu1 O5 71.8(5) 4_565 . ? O3 Eu1 O2 69.7(3) 3_666 3_666 ? O4 Eu1 O2 131.9(4) 4_565 3_666 ? O5 Eu1 O2 74.5(6) . 3_666 ? O3 Eu1 O6 88.9(4) 3_666 3_666 ? O4 Eu1 O6 144.9(3) 4_565 3_666 ? O5 Eu1 O6 143.0(5) . 3_666 ? O2 Eu1 O6 73.0(5) 3_666 3_666 ? O3 Eu1 O1 168.3(4) 3_666 . ? O4 Eu1 O1 94.7(4) 4_565 . ? O5 Eu1 O1 92.7(5) . . ? O2 Eu1 O1 120.3(4) 3_666 . ? O6 Eu1 O1 88.7(4) 3_666 . ? O3 Eu1 N1 82.5(3) 3_666 3_766 ? O4 Eu1 N1 71.9(3) 4_565 3_766 ? O5 Eu1 N1 143.4(5) . 3_766 ? O2 Eu1 N1 136.4(4) 3_666 3_766 ? O6 Eu1 N1 73.6(4) 3_666 3_766 ? O1 Eu1 N1 85.8(4) . 3_766 ? O3 Eu1 O2 140.1(3) 3_666 . ? O4 Eu1 O2 131.5(4) 4_565 . ? O5 Eu1 O2 77.8(5) . . ? O2 Eu1 O2 70.7(3) 3_666 . ? O6 Eu1 O2 75.2(4) 3_666 . ? O1 Eu1 O2 49.7(3) . . ? N1 Eu1 O2 125.2(4) 3_766 . ? O3 Eu1 C1 164.0(3) 3_666 . ? O4 Eu1 C1 114.6(4) 4_565 . ? O5 Eu1 C1 85.3(5) . . ? O2 Eu1 C1 95.5(3) 3_666 . ? O6 Eu1 C1 80.7(3) 3_666 . ? O1 Eu1 C1 24.9(4) . . ? N1 Eu1 C1 105.8(3) 3_766 . ? O2 Eu1 C1 24.8(3) . . ? O3 Eu1 S1 112.5(3) 3_666 3_656 ? O4 Eu1 S1 59.2(3) 4_565 3_656 ? O5 Eu1 S1 24.9(4) . 3_656 ? O2 Eu1 S1 97.9(4) 3_666 3_656 ? O6 Eu1 S1 152.7(3) 3_666 3_656 ? O1 Eu1 S1 73.6(3) . 3_656 ? N1 Eu1 S1 124.0(3) 3_766 3_656 ? O2 Eu1 S1 77.6(4) . 3_656 ? C1 Eu1 S1 74.6(3) . 3_656 ? O3 Eu1 Eu1 106.4(2) 3_666 3_666 ? O4 Eu1 Eu1 144.7(2) 4_565 3_666 ? O5 Eu1 Eu1 73.1(4) . 3_666 ? O2 Eu1 Eu1 36.8(2) 3_666 3_666 ? O6 Eu1 Eu1 70.4(2) 3_666 3_666 ? O1 Eu1 Eu1 83.5(3) . 3_666 ? N1 Eu1 Eu1 142.6(2) 3_766 3_666 ? O2 Eu1 Eu1 33.9(2) . 3_666 ? C1 Eu1 Eu1 58.7(2) . 3_666 ? S1 Eu1 Eu1 86.86(9) 3_656 3_666 ? O6 S1 O7 100.6(11) . . ? O6 S1 O5 118.6(9) . . ? O7 S1 O5 113.6(11) . . ? O6 S1 O5 119.1(8) . 3_656 ? O7 S1 O5 111.7(12) . 3_656 ? O5 S1 O5 94.0(9) . 3_656 ? O6 S1 S1 135.0(7) . 3_656 ? O7 S1 S1 124.2(10) . 3_656 ? O5 S1 S1 50.3(7) . 3_656 ? O5 S1 S1 43.7(6) 3_656 3_656 ? O6 S1 Eu1 114.4(5) . 3_656 ? O7 S1 Eu1 78.6(10) . 3_656 ? O5 S1 Eu1 121.0(7) . 3_656 ? O5 S1 Eu1 35.9(6) 3_656 3_656 ? S1 S1 Eu1 74.5(3) 3_656 3_656 ? C1 O1 Eu1 100.2(9) . . ? C1 O2 Eu1 157.6(9) . 3_666 ? C1 O2 Eu1 92.8(7) . . ? Eu1 O2 Eu1 109.3(3) 3_666 . ? C8 O3 Eu1 152.2(9) . 3_666 ? C8 O4 Eu1 155.2(10) . 4_566 ? S1 O5 S1 86.0(9) . 3_656 ? S1 O5 Eu1 135.8(10) . . ? S1 O5 Eu1 119.3(9) 3_656 . ? S1 O6 Eu1 140.5(7) . 3_666 ? O8 O8 H8A 78.4 3_556 . ? O8 O8 H8B 58.1 3_556 . ? H8A O8 H8B 109.5 . . ? C5 N2 C9 106.2(10) . . ? C5 N2 H2 126.9 . . ? C9 N2 H2 126.9 . . ? C9 N1 C4 105.7(9) . . ? C9 N1 Eu1 117.1(7) . 3_766 ? C4 N1 Eu1 133.6(7) . 3_766 ? O2 C1 O1 117.2(12) . . ? O2 C1 C2 124.9(11) . . ? O1 C1 C2 117.8(11) . . ? O2 C1 Eu1 62.3(7) . . ? O1 C1 Eu1 54.9(7) . . ? C2 C1 Eu1 172.5(8) . . ? C3 C2 C7 117.9(10) . . ? C3 C2 C1 114.0(10) . . ? C7 C2 C1 128.1(10) . . ? C4 C3 C2 120.6(11) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 119.6(11) . . ? C5 C4 N1 109.5(10) . . ? C3 C4 N1 130.9(11) . . ? C4 C5 C6 121.7(11) . . ? C4 C5 N2 106.6(10) . . ? C6 C5 N2 131.7(11) . . ? C7 C6 C5 119.3(11) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C2 120.9(10) . . ? C6 C7 C8 113.9(10) . . ? C2 C7 C8 125.1(10) . . ? O3 C8 O4 122.2(11) . . ? O3 C8 C7 121.5(10) . . ? O4 C8 C7 116.0(10) . . ? N1 C9 N2 111.9(10) . . ? N1 C9 H9 124.0 . . ? N2 C9 H9 124.0 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 3.456 _refine_diff_density_min -2.062 _refine_diff_density_rms 0.299 # Attachment 'Gd.cif' data_Gd _database_code_depnum_ccdc_archive 'CCDC 734652' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 Gd2 N4 O15 S' _chemical_formula_sum 'C18 H14 Gd2 N4 O15 S' _chemical_formula_weight 872.89 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4361(15) _cell_length_b 9.8459(15) _cell_length_c 14.246(2) _cell_angle_alpha 91.443(2) _cell_angle_beta 107.665(2) _cell_angle_gamma 118.251(2) _cell_volume 1088.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1372 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 24.21 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 6.233 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.195 _exptl_absorpt_correction_T_max 0.347 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 area-detector diffractometer' _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 5873 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3954 _reflns_number_gt 3582 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material 'SHELXTL(Bruker, 2002)' _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^)+(0.0394P)^2^+2.5388P] 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 3954 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.8462(7) 0.2904(7) 0.7479(4) 0.0152(12) Uani 1 1 d . . . C2 C 0.7998(7) 0.1579(6) 0.8024(4) 0.0133(11) Uani 1 1 d . . . C3 C 0.8752(7) 0.1943(7) 0.9072(4) 0.0158(12) Uani 1 1 d . . . H3 H 0.9458 0.2981 0.9421 0.019 Uiso 1 1 calc R . . C4 C 0.8412(7) 0.0702(7) 0.9574(4) 0.0146(12) Uani 1 1 d . . . C5 C 0.8434(8) -0.0792(7) 1.0642(4) 0.0166(12) Uani 1 1 d . . . H5 H 0.8690 -0.1136 1.1240 0.020 Uiso 1 1 calc R . . C6 C 0.7299(7) -0.0859(6) 0.9036(4) 0.0131(12) Uani 1 1 d . . . C7 C 0.6474(7) -0.1231(6) 0.8001(4) 0.0149(12) Uani 1 1 d . . . H7 H 0.5706 -0.2268 0.7660 0.018 Uiso 1 1 calc R . . C8 C 0.6846(7) 0.0013(6) 0.7497(4) 0.0111(11) Uani 1 1 d . . . C9 C 0.5882(7) -0.0372(6) 0.6398(4) 0.0132(11) Uani 1 1 d . . . C10 C 0.8229(7) -0.1238(6) 0.3600(4) 0.0118(11) Uani 1 1 d . . . C11 C 0.6881(7) -0.1607(7) 0.2584(4) 0.0124(11) Uani 1 1 d . . . C12 C 0.5901(8) -0.3161(7) 0.2077(4) 0.0169(12) Uani 1 1 d . . . H12 H 0.6057 -0.3938 0.2370 0.020 Uiso 1 1 calc R . . C13 C 0.4680(8) -0.3539(7) 0.1123(4) 0.0169(12) Uani 1 1 d . . . C14 C 0.2766(8) -0.4653(7) -0.0361(5) 0.0257(14) Uani 1 1 d . . . H14 H 0.1958 -0.5403 -0.0942 0.031 Uiso 1 1 calc R . . C15 C 0.4434(7) -0.2370(7) 0.0684(4) 0.0149(12) Uani 1 1 d . . . C16 C 0.5419(7) -0.0809(7) 0.1172(4) 0.0150(12) Uani 1 1 d . . . H16 H 0.5263 -0.0038 0.0872 0.018 Uiso 1 1 calc R . . C17 C 0.6635(7) -0.0430(6) 0.2110(4) 0.0122(11) Uani 1 1 d . . . C18 C 0.7882(7) 0.1258(6) 0.2579(4) 0.0109(11) Uani 1 1 d . . . Gd1 Gd 0.82355(3) 0.13818(3) 0.509433(19) 0.00953(9) Uani 1 1 d . . . Gd2 Gd 1.09627(3) 0.43382(3) 0.34318(2) 0.01165(9) Uani 1 1 d . . . N1 N 0.9098(7) 0.0710(6) 1.0585(4) 0.0185(11) Uani 1 1 d . . . N2 N 0.7357(6) -0.1765(6) 0.9754(4) 0.0176(11) Uani 1 1 d . . . H2 H 0.6800 -0.2776 0.9649 0.021 Uiso 1 1 calc R . . N3 N 0.3580(7) -0.4984(6) 0.0448(4) 0.0271(13) Uani 1 1 d . . . N4 N 0.3213(6) -0.3138(6) -0.0264(4) 0.0213(11) Uani 1 1 d . . . H4 H 0.2811 -0.2715 -0.0712 0.026 Uiso 1 1 calc R . . O1 O 0.9167(6) 0.4297(5) 0.7951(3) 0.0214(9) Uani 1 1 d . . . O2 O 0.8151(5) 0.2654(5) 0.6536(3) 0.0172(9) Uani 1 1 d . . . O3 O 0.6500(5) -0.0631(4) 0.5786(3) 0.0168(9) Uani 1 1 d . . . O4 O 0.4464(5) -0.0426(5) 0.6135(3) 0.0228(10) Uani 1 1 d . . . O5 O 0.7947(5) -0.0984(4) 0.4387(3) 0.0154(8) Uani 1 1 d . . . O6 O 0.9519(5) -0.1320(5) 0.3607(3) 0.0200(9) Uani 1 1 d . . . O8 O 0.8769(5) 0.1684(4) 0.3524(3) 0.0170(9) Uani 1 1 d . . . O7 O 0.8169(5) 0.2276(5) 0.2039(3) 0.0175(9) Uani 1 1 d . . . O9 O 1.0953(5) 0.3628(5) 0.5164(3) 0.0188(9) Uani 1 1 d . . . O10 O 1.1426(5) 0.5422(5) 0.6564(3) 0.0168(9) Uani 1 1 d . . . O11 O 1.3847(5) 0.5430(5) 0.6325(3) 0.0186(9) Uani 1 1 d . . . O12 O 1.2211(5) 0.6317(5) 0.5127(3) 0.0187(9) Uani 1 1 d . . . O13 O 1.1615(6) 0.3338(5) 0.2104(3) 0.0272(10) Uani 1 1 d . . . H13A H 1.0942 0.3282 0.1531 0.041 Uiso 1 1 d R . . H13C H 1.1467 0.2428 0.2163 0.041 Uiso 1 1 d R . . O14 O 1.4063(6) 0.6008(5) 0.3829(4) 0.0308(11) Uani 1 1 d . . . H14B H 1.4397 0.6924 0.4125 0.046 Uiso 1 1 d R . . H14C H 1.4588 0.5614 0.4212 0.046 Uiso 1 1 d R . . O15 O 1.2408(7) 0.2871(6) 0.4061(4) 0.0372(13) Uani 1 1 d . . . H15A H 1.2385 0.2348 0.3568 0.056 Uiso 1 1 d R . . H15C H 1.1889 0.2244 0.4398 0.056 Uiso 1 1 d R . . S1 S 1.21603(17) 0.52229(15) 0.58369(10) 0.0107(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.015(3) 0.018(3) 0.015(3) 0.007(2) 0.005(2) 0.011(3) C2 0.016(3) 0.012(3) 0.014(3) 0.006(2) 0.006(2) 0.008(2) C3 0.014(3) 0.011(3) 0.019(3) 0.002(2) 0.006(3) 0.004(2) C4 0.013(3) 0.018(3) 0.014(3) 0.003(2) 0.005(2) 0.008(2) C5 0.024(3) 0.024(3) 0.014(3) 0.012(2) 0.011(3) 0.019(3) C6 0.013(3) 0.012(3) 0.016(3) 0.008(2) 0.008(2) 0.006(2) C7 0.014(3) 0.010(3) 0.021(3) 0.005(2) 0.006(3) 0.005(2) C8 0.007(3) 0.016(3) 0.011(3) 0.002(2) 0.001(2) 0.008(2) C9 0.011(3) 0.007(3) 0.018(3) 0.002(2) 0.004(2) 0.003(2) C10 0.013(3) 0.010(3) 0.009(3) 0.002(2) -0.002(2) 0.007(2) C11 0.013(3) 0.018(3) 0.007(3) 0.004(2) 0.003(2) 0.009(2) C12 0.019(3) 0.010(3) 0.017(3) 0.007(2) 0.002(3) 0.007(3) C13 0.018(3) 0.012(3) 0.015(3) 0.005(2) 0.000(3) 0.007(2) C14 0.020(3) 0.019(3) 0.016(3) -0.004(3) -0.007(3) 0.002(3) C15 0.011(3) 0.014(3) 0.019(3) 0.004(2) 0.003(2) 0.007(2) C16 0.018(3) 0.017(3) 0.015(3) 0.008(2) 0.008(3) 0.011(3) C17 0.010(3) 0.011(3) 0.015(3) 0.002(2) 0.007(2) 0.004(2) C18 0.009(3) 0.011(3) 0.014(3) 0.001(2) 0.003(2) 0.007(2) Gd1 0.00853(15) 0.00985(15) 0.00880(15) 0.00195(11) 0.00131(11) 0.00465(12) Gd2 0.01174(16) 0.01008(15) 0.01249(16) 0.00281(11) 0.00359(12) 0.00543(12) N1 0.021(3) 0.020(3) 0.014(3) 0.005(2) 0.005(2) 0.011(2) N2 0.022(3) 0.013(2) 0.017(3) 0.007(2) 0.007(2) 0.007(2) N3 0.028(3) 0.014(3) 0.022(3) 0.003(2) -0.002(3) 0.005(2) N4 0.017(3) 0.017(3) 0.015(3) -0.001(2) -0.007(2) 0.006(2) O1 0.029(2) 0.011(2) 0.016(2) 0.0025(17) 0.0033(19) 0.0068(19) O2 0.023(2) 0.015(2) 0.013(2) 0.0040(16) 0.0063(18) 0.0088(18) O3 0.022(2) 0.015(2) 0.014(2) 0.0061(16) 0.0087(18) 0.0080(18) O4 0.014(2) 0.031(2) 0.023(2) 0.0043(19) 0.0009(19) 0.014(2) O5 0.020(2) 0.015(2) 0.012(2) 0.0022(16) 0.0020(18) 0.0121(18) O6 0.015(2) 0.030(2) 0.014(2) 0.0034(18) -0.0002(18) 0.014(2) O8 0.019(2) 0.014(2) 0.011(2) 0.0011(16) 0.0026(18) 0.0052(18) O7 0.024(2) 0.015(2) 0.014(2) 0.0081(17) 0.0058(18) 0.0110(18) O9 0.014(2) 0.014(2) 0.018(2) -0.0028(17) 0.0001(18) 0.0042(18) O10 0.015(2) 0.021(2) 0.014(2) 0.0009(17) 0.0042(18) 0.0105(18) O11 0.010(2) 0.023(2) 0.016(2) -0.0010(17) -0.0034(17) 0.0089(18) O12 0.022(2) 0.016(2) 0.021(2) 0.0093(17) 0.0082(19) 0.0111(19) O13 0.033(3) 0.028(2) 0.023(2) -0.001(2) 0.007(2) 0.019(2) O14 0.019(2) 0.027(3) 0.043(3) 0.001(2) 0.008(2) 0.011(2) O15 0.055(3) 0.047(3) 0.047(3) 0.028(3) 0.032(3) 0.044(3) S1 0.0102(6) 0.0097(6) 0.0108(7) 0.0019(5) 0.0013(6) 0.0053(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.262(7) . ? C1 O2 1.276(7) . ? C1 C2 1.488(8) . ? C1 Gd2 2.926(6) 2_766 ? C2 C3 1.397(8) . ? C2 C8 1.408(8) . ? C3 C4 1.385(8) . ? C3 H3 0.9300 . ? C4 N1 1.386(8) . ? C4 C6 1.406(8) . ? C5 N1 1.321(8) . ? C5 N2 1.337(8) . ? C5 H5 0.9300 . ? C6 N2 1.381(7) . ? C6 C7 1.385(8) . ? C7 C8 1.389(8) . ? C7 H7 0.9300 . ? C8 C9 1.483(8) . ? C9 O4 1.250(7) . ? C9 O3 1.266(7) . ? C10 O6 1.254(7) . ? C10 O5 1.273(7) . ? C10 C11 1.505(7) . ? C11 C12 1.384(8) . ? C11 C17 1.433(8) . ? C12 C13 1.390(8) . ? C12 H12 0.9300 . ? C13 N3 1.398(8) . ? C13 C15 1.404(8) . ? C14 N3 1.320(8) . ? C14 N4 1.335(8) . ? C14 H14 0.9300 . ? C15 N4 1.379(8) . ? C15 C16 1.382(8) . ? C16 C17 1.372(8) . ? C16 H16 0.9300 . ? C17 C18 1.486(7) . ? C18 O7 1.256(6) . ? C18 O8 1.282(7) . ? C18 Gd2 2.907(5) . ? Gd1 O4 2.320(4) 2_656 ? Gd1 O3 2.363(4) . ? Gd1 O5 2.372(4) . ? Gd1 O6 2.380(4) 2_756 ? Gd1 O2 2.420(4) . ? Gd1 O8 2.433(4) . ? Gd1 O9 2.438(4) . ? Gd1 O12 2.504(4) 2_766 ? Gd2 O10 2.376(4) 2_766 ? Gd2 O1 2.417(4) 2_766 ? Gd2 O15 2.437(4) . ? Gd2 O14 2.445(4) . ? Gd2 O13 2.473(4) . ? Gd2 O8 2.489(4) . ? Gd2 O7 2.562(4) . ? Gd2 O9 2.583(4) . ? Gd2 O12 2.623(4) . ? Gd2 O2 2.663(4) 2_766 ? Gd2 C1 2.926(6) 2_766 ? N2 H2 0.8600 . ? N4 H4 0.8600 . ? O1 Gd2 2.417(4) 2_766 ? O2 Gd2 2.663(4) 2_766 ? O4 Gd1 2.320(4) 2_656 ? O6 Gd1 2.380(4) 2_756 ? O9 S1 1.500(4) . ? O10 S1 1.465(4) . ? O10 Gd2 2.376(4) 2_766 ? O11 S1 1.439(4) . ? O12 S1 1.490(4) . ? O12 Gd1 2.504(4) 2_766 ? O13 H13A 0.8500 . ? O13 H13C 0.8500 . ? O14 H14B 0.8500 . ? O14 H14C 0.8500 . ? O15 H15A 0.8499 . ? O15 H15C 0.8502 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 119.2(5) . . ? O1 C1 C2 119.9(5) . . ? O2 C1 C2 120.9(5) . . ? O1 C1 Gd2 54.3(3) . 2_766 ? O2 C1 Gd2 65.5(3) . 2_766 ? C2 C1 Gd2 169.9(4) . 2_766 ? C3 C2 C8 121.3(5) . . ? C3 C2 C1 117.7(5) . . ? C8 C2 C1 120.9(5) . . ? C4 C3 C2 117.7(5) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C3 C4 N1 129.9(5) . . ? C3 C4 C6 120.3(5) . . ? N1 C4 C6 109.7(5) . . ? N1 C5 N2 113.1(5) . . ? N1 C5 H5 123.4 . . ? N2 C5 H5 123.4 . . ? N2 C6 C7 132.9(5) . . ? N2 C6 C4 104.5(5) . . ? C7 C6 C4 122.5(5) . . ? C6 C7 C8 117.0(5) . . ? C6 C7 H7 121.5 . . ? C8 C7 H7 121.5 . . ? C7 C8 C2 121.0(5) . . ? C7 C8 C9 117.2(5) . . ? C2 C8 C9 121.7(5) . . ? O4 C9 O3 123.6(5) . . ? O4 C9 C8 116.1(5) . . ? O3 C9 C8 120.2(5) . . ? O6 C10 O5 124.2(5) . . ? O6 C10 C11 116.3(5) . . ? O5 C10 C11 119.2(5) . . ? C12 C11 C17 119.6(5) . . ? C12 C11 C10 117.1(5) . . ? C17 C11 C10 123.2(5) . . ? C11 C12 C13 118.7(5) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C12 C13 N3 130.1(5) . . ? C12 C13 C15 120.7(5) . . ? N3 C13 C15 109.2(5) . . ? N3 C14 N4 113.5(5) . . ? N3 C14 H14 123.3 . . ? N4 C14 H14 123.3 . . ? N4 C15 C16 133.4(5) . . ? N4 C15 C13 105.0(5) . . ? C16 C15 C13 121.4(5) . . ? C17 C16 C15 118.1(5) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C16 C17 C11 121.5(5) . . ? C16 C17 C18 118.8(5) . . ? C11 C17 C18 119.2(5) . . ? O7 C18 O8 119.0(5) . . ? O7 C18 C17 120.0(5) . . ? O8 C18 C17 120.8(5) . . ? O7 C18 Gd2 61.7(3) . . ? O8 C18 Gd2 58.5(3) . . ? C17 C18 Gd2 164.9(4) . . ? O4 Gd1 O3 79.27(15) 2_656 . ? O4 Gd1 O5 82.99(14) 2_656 . ? O3 Gd1 O5 73.47(14) . . ? O4 Gd1 O6 157.80(15) 2_656 2_756 ? O3 Gd1 O6 81.91(14) . 2_756 ? O5 Gd1 O6 80.45(14) . 2_756 ? O4 Gd1 O2 104.95(14) 2_656 . ? O3 Gd1 O2 72.88(13) . . ? O5 Gd1 O2 143.15(13) . . ? O6 Gd1 O2 80.38(14) 2_756 . ? O4 Gd1 O8 75.26(14) 2_656 . ? O3 Gd1 O8 138.34(13) . . ? O5 Gd1 O8 71.17(13) . . ? O6 Gd1 O8 112.68(14) 2_756 . ? O2 Gd1 O8 145.63(13) . . ? O4 Gd1 O9 127.47(15) 2_656 . ? O3 Gd1 O9 152.97(14) . . ? O5 Gd1 O9 110.04(14) . . ? O6 Gd1 O9 72.61(14) 2_756 . ? O2 Gd1 O9 93.70(13) . . ? O8 Gd1 O9 63.05(13) . . ? O4 Gd1 O12 73.38(14) 2_656 2_766 ? O3 Gd1 O12 118.81(13) . 2_766 ? O5 Gd1 O12 149.76(13) . 2_766 ? O6 Gd1 O12 126.76(14) 2_756 2_766 ? O2 Gd1 O12 63.46(13) . 2_766 ? O8 Gd1 O12 84.55(13) . 2_766 ? O9 Gd1 O12 72.27(14) . 2_766 ? O10 Gd2 O1 83.06(14) 2_766 2_766 ? O10 Gd2 O15 140.93(15) 2_766 . ? O1 Gd2 O15 133.84(15) 2_766 . ? O10 Gd2 O14 139.21(15) 2_766 . ? O1 Gd2 O14 82.19(16) 2_766 . ? O15 Gd2 O14 70.23(17) . . ? O10 Gd2 O13 133.35(14) 2_766 . ? O1 Gd2 O13 68.50(15) 2_766 . ? O15 Gd2 O13 68.69(16) . . ? O14 Gd2 O13 74.03(15) . . ? O10 Gd2 O8 74.45(14) 2_766 . ? O1 Gd2 O8 128.19(14) 2_766 . ? O15 Gd2 O8 71.59(16) . . ? O14 Gd2 O8 141.73(15) . . ? O13 Gd2 O8 94.52(14) . . ? O10 Gd2 O7 68.42(13) 2_766 . ? O1 Gd2 O7 77.14(13) 2_766 . ? O15 Gd2 O7 103.16(16) . . ? O14 Gd2 O7 142.72(14) . . ? O13 Gd2 O7 69.63(14) . . ? O8 Gd2 O7 51.30(12) . . ? O10 Gd2 O9 82.54(13) 2_766 . ? O1 Gd2 O9 159.95(13) 2_766 . ? O15 Gd2 O9 64.15(15) . . ? O14 Gd2 O9 99.91(15) . . ? O13 Gd2 O9 131.38(14) . . ? O8 Gd2 O9 60.25(13) . . ? O7 Gd2 O9 110.09(12) . . ? O10 Gd2 O12 77.01(13) 2_766 . ? O1 Gd2 O12 109.44(13) 2_766 . ? O15 Gd2 O12 96.92(16) . . ? O14 Gd2 O12 72.53(14) . . ? O13 Gd2 O12 146.43(14) . . ? O8 Gd2 O12 109.92(12) . . ? O7 Gd2 O12 143.86(13) . . ? O9 Gd2 O12 53.50(12) . . ? O10 Gd2 O2 72.46(13) 2_766 2_766 ? O1 Gd2 O2 50.76(13) 2_766 2_766 ? O15 Gd2 O2 136.99(16) . 2_766 ? O14 Gd2 O2 68.75(14) . 2_766 ? O13 Gd2 O2 110.89(14) . 2_766 ? O8 Gd2 O2 146.69(13) . 2_766 ? O7 Gd2 O2 117.20(12) . 2_766 ? O9 Gd2 O2 111.17(12) . 2_766 ? O12 Gd2 O2 58.68(12) . 2_766 ? O10 Gd2 C18 72.28(14) 2_766 . ? O1 Gd2 C18 102.71(15) 2_766 . ? O15 Gd2 C18 85.03(17) . . ? O14 Gd2 C18 148.27(15) . . ? O13 Gd2 C18 78.71(15) . . ? O8 Gd2 C18 26.05(14) . . ? O7 Gd2 C18 25.57(14) . . ? O9 Gd2 C18 86.07(14) . . ? O12 Gd2 C18 131.84(13) . . ? O2 Gd2 C18 137.95(14) 2_766 . ? O10 Gd2 C1 78.68(14) 2_766 2_766 ? O1 Gd2 C1 25.09(15) 2_766 2_766 ? O15 Gd2 C1 139.81(16) . 2_766 ? O14 Gd2 C1 72.02(16) . 2_766 ? O13 Gd2 C1 88.20(15) . 2_766 ? O8 Gd2 C1 145.35(15) . 2_766 ? O7 Gd2 C1 98.45(14) . 2_766 ? O9 Gd2 C1 136.88(14) . 2_766 ? O12 Gd2 C1 84.42(14) . 2_766 ? O2 Gd2 C1 25.85(14) 2_766 2_766 ? C18 Gd2 C1 123.40(16) . 2_766 ? C5 N1 C4 104.8(5) . . ? C5 N2 C6 107.9(5) . . ? C5 N2 H2 126.1 . . ? C6 N2 H2 126.1 . . ? C14 N3 C13 104.6(5) . . ? C14 N4 C15 107.8(5) . . ? C14 N4 H4 126.1 . . ? C15 N4 H4 126.1 . . ? C1 O1 Gd2 100.6(3) . 2_766 ? C1 O2 Gd1 150.0(4) . . ? C1 O2 Gd2 88.6(3) . 2_766 ? Gd1 O2 Gd2 114.57(14) . 2_766 ? C9 O3 Gd1 122.5(3) . . ? C9 O4 Gd1 147.4(4) . 2_656 ? C10 O5 Gd1 127.0(3) . . ? C10 O6 Gd1 132.9(4) . 2_756 ? C18 O8 Gd1 137.7(3) . . ? C18 O8 Gd2 95.5(3) . . ? Gd1 O8 Gd2 117.24(15) . . ? C18 O7 Gd2 92.7(3) . . ? S1 O9 Gd1 134.3(2) . . ? S1 O9 Gd2 100.5(2) . . ? Gd1 O9 Gd2 113.61(15) . . ? S1 O10 Gd2 138.4(2) . 2_766 ? S1 O12 Gd1 139.7(2) . 2_766 ? S1 O12 Gd2 99.14(19) . . ? Gd1 O12 Gd2 113.13(15) 2_766 . ? Gd2 O13 H13A 109.3 . . ? Gd2 O13 H13C 109.4 . . ? H13A O13 H13C 109.5 . . ? Gd2 O14 H14B 109.4 . . ? Gd2 O14 H14C 109.2 . . ? H14B O14 H14C 109.5 . . ? Gd2 O15 H15A 109.3 . . ? Gd2 O15 H15C 109.3 . . ? H15A O15 H15C 109.5 . . ? O11 S1 O10 111.9(2) . . ? O11 S1 O12 110.7(2) . . ? O10 S1 O12 110.7(2) . . ? O11 S1 O9 110.9(2) . . ? O10 S1 O9 109.1(2) . . ? O12 S1 O9 103.2(2) . . ? O11 S1 Gd2 111.11(18) . . ? O10 S1 Gd2 136.95(17) . . ? O12 S1 Gd2 53.64(16) . . ? O9 S1 Gd2 52.16(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O15 H15C O5 0.85 2.16 2.918(6) 147.7 2_756 O14 H14C O11 0.85 2.43 2.971(6) 122.2 2_866 O13 H13A N1 0.85 2.34 2.792(7) 113.5 1_554 N4 H4 O7 0.86 1.99 2.823(7) 161.6 2_655 N2 H2 N3 0.86 2.05 2.869(7) 158.0 2_646 O13 H13C O15 0.85 2.53 2.770(7) 97.2 . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.057 _refine_diff_density_min -1.637 _refine_diff_density_rms 0.198 # Attachment 'La.cif' data_La _database_code_depnum_ccdc_archive 'CCDC 734653' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 La2 N4 O15 S' _chemical_formula_sum 'C18 H14 La2 N4 O15 S' _chemical_formula_weight 836.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' La La -0.2871 2.4523 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6550(17) _cell_length_b 10.0259(18) _cell_length_c 14.313(3) _cell_angle_alpha 91.012(2) _cell_angle_beta 107.625(2) _cell_angle_gamma 118.626(2) _cell_volume 1136.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2794 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 23.31 _exptl_crystal_description sheet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 3.890 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.390 _exptl_absorpt_correction_T_max 0.496 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 area-detector diffractometer' _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 5858 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3919 _reflns_number_gt 3495 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material 'SHELXTL(Bruker, 2002)' _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^)+(0.0000P)^2^+2.9715P] 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 3919 _refine_ls_number_parameters 367 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.232 _refine_ls_restrained_S_all 1.232 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O10 O 0.8617(11) 0.4645(10) -0.1528(7) 0.024(2) Uani 1 1 d . . . O12 O 0.8967(10) 0.6348(9) -0.0162(6) 0.0174(17) Uani 1 1 d . . . S1 S 0.7837(3) 0.4781(3) -0.0836(2) 0.0122(6) Uani 1 1 d . . . O9 O 0.7778(11) 0.3687(9) -0.0134(6) 0.0213(19) Uani 1 1 d . . . C1 C 0.7824(14) 0.1196(13) -0.2480(9) 0.015(2) Uani 1 1 d . . . C2 C 0.6664(15) -0.0442(14) -0.2908(9) 0.017(2) Uani 1 1 d . . . C3 C 0.5436(15) -0.0810(13) -0.3851(9) 0.018(3) Uani 1 1 d . . . H3 H 0.5287 -0.0049 -0.4151 0.022 Uiso 1 1 calc R . . C4 C 0.4439(15) -0.2374(14) -0.4325(9) 0.017(2) Uani 1 1 d . . . C5 C 0.2739(17) -0.4615(15) -0.5326(10) 0.027(3) Uani 1 1 d . . . H5 H 0.1915 -0.5367 -0.5888 0.033 Uiso 1 1 calc R . . C6 C 0.4660(15) -0.3502(14) -0.3868(9) 0.021(3) Uani 1 1 d . . . C7 C 0.5865(15) -0.3144(14) -0.2942(9) 0.021(3) Uani 1 1 d . . . H7 H 0.6025 -0.3906 -0.2653 0.026 Uiso 1 1 calc R . . C8 C 0.6838(14) -0.1605(13) -0.2453(8) 0.014(2) Uani 1 1 d . . . C9 C 0.8157(13) -0.1340(13) -0.1483(8) 0.012(4) Uani 1.00(5) 1 d . . . C10 C 0.5864(14) -0.0432(13) 0.1495(8) 0.014(4) Uani 1.00(5) 1 d U . . C11 C 0.6817(14) -0.0028(14) 0.2571(8) 0.015(2) Uani 1 1 d . . . C12 C 0.6472(14) -0.1261(14) 0.3053(9) 0.019(3) Uani 1 1 d . . . H12 H 0.5722 -0.2277 0.2707 0.023 Uiso 1 1 calc R . . C13 C 0.7298(14) -0.0918(13) 0.4085(9) 0.015(2) Uani 1 1 d . . . C14 C 0.8438(16) -0.0883(15) 0.5662(9) 0.020(3) Uani 1 1 d . . . H14 H 0.8701 -0.1245 0.6246 0.024 Uiso 1 1 calc R . . C15 C 0.8365(14) 0.0596(14) 0.4617(8) 0.016(2) Uani 1 1 d . . . C16 C 0.8685(14) 0.1854(13) 0.4128(9) 0.015(2) Uani 1 1 d . . . H16 H 0.9372 0.2871 0.4481 0.018 Uiso 1 1 calc R . . C17 C 0.7933(14) 0.1517(14) 0.3096(9) 0.016(2) Uani 1 1 d . . . C18 C 0.8379(14) 0.2851(14) 0.2560(9) 0.017(2) Uani 1 1 d . . . La1 La 0.82239(8) 0.13631(7) 0.01157(5) 0.01214(18) Uani 1 1 d . . . La2 La 0.89847(8) 0.56350(7) 0.16130(5) 0.01316(19) Uani 1 1 d . . . N1 N 0.3200(13) -0.3115(12) -0.5262(8) 0.023(2) Uani 1 1 d . . . N2 N 0.3540(15) -0.4930(13) -0.4536(8) 0.032(3) Uani 1 1 d . . . N4 N 0.7355(13) -0.1827(11) 0.4770(8) 0.019(2) Uani 1 1 d . . . H4 H 0.6802 -0.2823 0.4656 0.023 Uiso 1 1 calc R . . N3 N 0.9089(12) 0.0601(11) 0.5626(7) 0.017(2) Uani 1 1 d . . . O1 O 0.8091(11) 0.2233(9) -0.2998(6) 0.024(2) Uani 1 1 d . . . O2 O 0.8748(10) 0.1618(9) -0.1522(6) 0.0173(17) Uani 1 1 d . . . O3 O 0.7860(11) -0.1081(9) -0.0659(6) 0.0207(18) Uani 1 1 d . . . O4 O 0.9486(10) -0.1260(11) -0.1429(7) 0.025(2) Uani 1 1 d . . . O5 O 0.6467(10) -0.0675(9) 0.0861(6) 0.0206(18) Uani 1 1 d . . . O6 O 0.4522(10) -0.0359(10) 0.1188(7) 0.026(2) Uani 1 1 d . . . O7 O 0.9097(12) 0.4196(10) 0.3046(7) 0.030(2) Uani 1 1 d . . . O8 O 0.8087(10) 0.2627(9) 0.1618(6) 0.0184(18) Uani 1 1 d . . . O11 O 0.6179(10) 0.4555(10) -0.1351(6) 0.0223(19) Uani 1 1 d . . . O15 O 0.5793(12) 0.3988(12) 0.1150(9) 0.043(3) Uani 1 1 d . . . H15A H 0.5555 0.3115 0.1316 0.051 Uiso 1 1 d R . . H15B H 0.5398 0.4404 0.1432 0.051 Uiso 1 1 d R . . O13 O 0.8435(12) 0.6712(11) 0.3008(7) 0.032(2) Uani 1 1 d . . . H13B H 0.9341 0.7462 0.3422 0.038 Uiso 1 1 d R . . H13A H 0.7959 0.6014 0.3317 0.038 Uiso 1 1 d R . . O14 O 0.7566(14) 0.7184(12) 0.0956(8) 0.039(3) Uani 1 1 d . . . H14A H 0.7650 0.7868 0.1365 0.047 Uiso 1 1 d R . . H14B H 0.8003 0.7461 0.0509 0.047 Uiso 1 1 d R . . H1 H 0.277(18) -0.288(16) -0.583(11) 0.03(4) 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 O10 0.022(4) 0.031(5) 0.025(5) 0.001(4) 0.012(4) 0.017(4) O12 0.016(4) 0.008(4) 0.019(4) -0.003(3) 0.001(3) 0.002(3) S1 0.0124(13) 0.0101(13) 0.0124(14) 0.0017(11) 0.0020(11) 0.0060(11) O9 0.025(5) 0.013(4) 0.022(5) 0.007(4) 0.004(4) 0.010(4) C1 0.018(6) 0.011(6) 0.016(6) 0.000(5) 0.005(5) 0.009(5) C2 0.018(6) 0.016(6) 0.019(6) 0.000(5) 0.007(5) 0.011(5) C3 0.019(6) 0.009(6) 0.023(7) 0.002(5) 0.005(5) 0.006(5) C4 0.020(6) 0.020(6) 0.013(6) 0.006(5) 0.008(5) 0.009(5) C5 0.029(7) 0.016(6) 0.018(7) -0.002(5) -0.004(6) 0.005(6) C6 0.018(6) 0.015(6) 0.019(6) -0.004(5) 0.000(5) 0.005(5) C7 0.019(6) 0.014(6) 0.019(6) 0.006(5) -0.001(5) 0.004(5) C8 0.012(5) 0.012(6) 0.012(6) -0.002(4) 0.002(5) 0.002(5) C9 0.007(6) 0.013(6) 0.018(7) 0.011(5) 0.004(5) 0.006(5) C10 0.011(4) 0.017(5) 0.015(5) -0.001(3) 0.006(3) 0.006(3) C11 0.011(5) 0.021(6) 0.004(5) -0.003(5) -0.004(4) 0.005(5) C12 0.015(6) 0.016(6) 0.023(7) 0.004(5) 0.006(5) 0.006(5) C13 0.014(5) 0.013(6) 0.019(6) 0.003(5) 0.009(5) 0.005(5) C14 0.030(7) 0.029(7) 0.017(6) 0.012(5) 0.015(5) 0.023(6) C15 0.017(6) 0.021(6) 0.011(6) 0.005(5) 0.007(5) 0.010(5) C16 0.016(6) 0.011(6) 0.015(6) 0.002(5) 0.008(5) 0.004(5) C17 0.018(6) 0.019(6) 0.017(6) 0.007(5) 0.006(5) 0.013(5) C18 0.016(6) 0.018(6) 0.018(6) 0.006(5) 0.005(5) 0.010(5) La1 0.0118(3) 0.0110(3) 0.0135(4) 0.0035(3) 0.0038(3) 0.0060(3) La2 0.0138(3) 0.0116(3) 0.0139(4) 0.0022(3) 0.0043(3) 0.0066(3) N1 0.021(5) 0.022(6) 0.015(6) 0.004(5) -0.004(4) 0.008(5) N2 0.037(7) 0.018(6) 0.022(6) 0.003(5) -0.002(5) 0.007(5) N4 0.028(6) 0.011(5) 0.020(6) 0.012(4) 0.010(5) 0.010(4) N3 0.015(5) 0.021(5) 0.011(5) 0.001(4) 0.002(4) 0.009(4) O1 0.029(5) 0.014(4) 0.019(5) 0.006(4) 0.005(4) 0.006(4) O2 0.018(4) 0.013(4) 0.010(4) 0.001(3) 0.001(3) 0.002(3) O3 0.028(5) 0.017(4) 0.018(4) 0.003(3) 0.006(4) 0.013(4) O4 0.016(4) 0.033(5) 0.024(5) 0.004(4) 0.000(4) 0.015(4) O5 0.020(4) 0.017(4) 0.025(5) 0.005(4) 0.014(4) 0.007(4) O6 0.013(4) 0.030(5) 0.028(5) 0.005(4) 0.000(4) 0.010(4) O7 0.045(6) 0.017(5) 0.018(5) 0.005(4) 0.006(4) 0.013(4) O8 0.024(4) 0.014(4) 0.012(4) 0.003(3) 0.006(3) 0.006(4) O11 0.015(4) 0.025(5) 0.021(5) 0.000(4) -0.003(4) 0.011(4) O15 0.021(5) 0.031(6) 0.071(8) 0.008(5) 0.021(5) 0.007(5) O13 0.033(5) 0.022(5) 0.033(6) -0.004(4) 0.014(4) 0.009(4) O14 0.061(7) 0.039(6) 0.050(7) 0.025(5) 0.030(6) 0.042(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O10 S1 1.454(9) . ? O10 La2 2.499(8) 2_765 ? O12 S1 1.502(8) . ? O12 La1 2.559(8) 2_765 ? O12 La2 2.649(8) . ? S1 O11 1.445(8) . ? S1 O9 1.494(8) . ? S1 La2 3.299(3) . ? O9 La1 2.576(8) . ? O9 La2 2.703(9) . ? C1 O1 1.258(14) . ? C1 O2 1.317(14) . ? C1 C2 1.454(16) . ? C1 La2 3.048(11) 2_765 ? C2 C3 1.400(17) . ? C2 C8 1.400(16) . ? C3 C4 1.403(17) . ? C3 H3 0.9300 . ? C4 N1 1.387(15) . ? C4 C6 1.387(17) . ? C5 N2 1.301(17) . ? C5 N1 1.340(17) . ? C5 H5 0.9300 . ? C6 C7 1.374(17) . ? C6 N2 1.405(16) . ? C7 C8 1.389(16) . ? C7 H7 0.9300 . ? C8 C9 1.488(15) . ? C9 O4 1.224(13) . ? C9 O3 1.344(14) . ? C10 O6 1.274(14) . ? C10 O5 1.291(14) . ? C10 C11 1.465(15) . ? C11 C12 1.376(17) . ? C11 C17 1.412(16) . ? C12 C13 1.393(17) . ? C12 H12 0.9300 . ? C13 N4 1.358(15) . ? C13 C15 1.390(17) . ? C14 N3 1.319(16) . ? C14 N4 1.349(16) . ? C14 H14 0.9300 . ? C15 N3 1.400(15) . ? C15 C16 1.402(16) . ? C16 C17 1.387(16) . ? C16 H16 0.9300 . ? C17 C18 1.498(16) . ? C18 O7 1.250(15) . ? C18 O8 1.284(14) . ? C18 La2 3.004(12) . ? La1 O6 2.430(8) 2_655 ? La1 O5 2.458(8) . ? La1 O4 2.479(8) 2_755 ? La1 O3 2.490(8) . ? La1 O2 2.536(8) . ? La1 O8 2.546(8) . ? La1 O12 2.559(8) 2_765 ? La2 O10 2.499(8) 2_765 ? La2 O7 2.534(9) . ? La2 O14 2.546(9) . ? La2 O15 2.552(9) . ? La2 O13 2.559(9) . ? La2 O2 2.608(8) 2_765 ? La2 O1 2.674(9) 2_765 ? La2 O8 2.710(8) . ? La2 C1 3.048(11) 2_765 ? N1 H1 0.89(15) . ? N4 H4 0.8600 . ? O1 La2 2.674(8) 2_765 ? O2 La2 2.608(8) 2_765 ? O4 La1 2.479(8) 2_755 ? O6 La1 2.430(8) 2_655 ? O15 H15A 0.8501 . ? O15 H15B 0.8500 . ? O13 H13B 0.8500 . ? O13 H13A 0.8500 . ? O14 H14A 0.8500 . ? O14 H14B 0.8501 . ? 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 S1 O10 La2 142.3(5) . 2_765 ? S1 O12 La1 131.2(5) . 2_765 ? S1 O12 La2 101.7(4) . . ? La1 O12 La2 113.5(3) 2_765 . ? O11 S1 O10 112.0(5) . . ? O11 S1 O9 111.3(5) . . ? O10 S1 O9 110.5(5) . . ? O11 S1 O12 110.4(5) . . ? O10 S1 O12 108.9(5) . . ? O9 S1 O12 103.5(5) . . ? O11 S1 La2 112.2(4) . . ? O10 S1 La2 135.7(4) . . ? O9 S1 La2 53.9(3) . . ? O12 S1 La2 51.8(3) . . ? S1 O9 La1 140.7(5) . . ? S1 O9 La2 99.6(4) . . ? La1 O9 La2 112.1(3) . . ? O1 C1 O2 117.7(10) . . ? O1 C1 C2 123.0(11) . . ? O2 C1 C2 119.1(10) . . ? O1 C1 La2 60.9(6) . 2_765 ? O2 C1 La2 58.3(5) . 2_765 ? C2 C1 La2 163.0(8) . 2_765 ? C3 C2 C8 120.8(11) . . ? C3 C2 C1 116.5(11) . . ? C8 C2 C1 122.5(10) . . ? C2 C3 C4 117.1(11) . . ? C2 C3 H3 121.4 . . ? C4 C3 H3 121.4 . . ? N1 C4 C6 106.9(11) . . ? N1 C4 C3 132.0(11) . . ? C6 C4 C3 121.1(11) . . ? N2 C5 N1 114.4(12) . . ? N2 C5 H5 122.8 . . ? N1 C5 H5 122.8 . . ? C7 C6 C4 121.9(11) . . ? C7 C6 N2 130.2(12) . . ? C4 C6 N2 107.8(11) . . ? C6 C7 C8 117.7(11) . . ? C6 C7 H7 121.1 . . ? C8 C7 H7 121.1 . . ? C7 C8 C2 121.3(11) . . ? C7 C8 C9 113.1(10) . . ? C2 C8 C9 125.3(10) . . ? O4 C9 O3 121.4(10) . . ? O4 C9 C8 122.5(11) . . ? O3 C9 C8 115.9(9) . . ? O6 C10 O5 120.0(11) . . ? O6 C10 C11 118.6(10) . . ? O5 C10 C11 120.9(10) . . ? C12 C11 C17 121.8(10) . . ? C12 C11 C10 115.2(10) . . ? C17 C11 C10 122.9(10) . . ? C11 C12 C13 116.9(11) . . ? C11 C12 H12 121.6 . . ? C13 C12 H12 121.6 . . ? N4 C13 C15 105.4(10) . . ? N4 C13 C12 132.3(11) . . ? C15 C13 C12 122.2(11) . . ? N3 C14 N4 113.6(10) . . ? N3 C14 H14 123.2 . . ? N4 C14 H14 123.2 . . ? C13 C15 N3 110.1(10) . . ? C13 C15 C16 120.9(11) . . ? N3 C15 C16 128.9(11) . . ? C17 C16 C15 117.1(11) . . ? C17 C16 H16 121.4 . . ? C15 C16 H16 121.4 . . ? C16 C17 C11 121.1(10) . . ? C16 C17 C18 117.4(11) . . ? C11 C17 C18 121.5(10) . . ? O7 C18 O8 120.0(11) . . ? O7 C18 C17 119.4(11) . . ? O8 C18 C17 120.6(10) . . ? O7 C18 La2 56.3(6) . . ? O8 C18 La2 64.5(6) . . ? C17 C18 La2 171.8(8) . . ? O6 La1 O5 80.4(3) 2_655 . ? O6 La1 O4 157.0(3) 2_655 2_755 ? O5 La1 O4 81.8(3) . 2_755 ? O6 La1 O3 80.5(3) 2_655 . ? O5 La1 O3 74.5(3) . . ? O4 La1 O3 80.7(3) 2_755 . ? O6 La1 O2 73.8(3) 2_655 . ? O5 La1 O2 138.0(3) . . ? O4 La1 O2 111.4(3) 2_755 . ? O3 La1 O2 69.1(3) . . ? O6 La1 O8 105.6(3) 2_655 . ? O5 La1 O8 71.1(3) . . ? O4 La1 O8 82.1(3) 2_755 . ? O3 La1 O8 143.3(3) . . ? O2 La1 O8 147.6(3) . . ? O6 La1 O12 127.0(3) 2_655 2_765 ? O5 La1 O12 152.5(3) . 2_765 ? O4 La1 O12 72.3(3) 2_755 2_765 ? O3 La1 O12 109.4(3) . 2_765 ? O2 La1 O12 63.2(3) . 2_765 ? O8 La1 O12 95.8(3) . 2_765 ? O6 La1 O9 73.7(3) 2_655 . ? O5 La1 O9 118.7(3) . . ? O4 La1 O9 128.2(3) 2_755 . ? O3 La1 O9 147.8(3) . . ? O2 La1 O9 85.2(3) . . ? O8 La1 O9 64.4(3) . . ? O12 La1 O9 73.1(3) 2_765 . ? O10 La2 O7 84.6(3) 2_765 . ? O10 La2 O14 138.9(3) 2_765 . ? O7 La2 O14 134.8(3) . . ? O10 La2 O15 139.2(3) 2_765 . ? O7 La2 O15 84.5(3) . . ? O14 La2 O15 69.0(3) . . ? O10 La2 O13 134.1(3) 2_765 . ? O7 La2 O13 68.9(3) . . ? O14 La2 O13 69.6(3) . . ? O15 La2 O13 76.4(3) . . ? O10 La2 O2 74.6(3) 2_765 2_765 ? O7 La2 O2 128.2(3) . 2_765 ? O14 La2 O2 70.7(3) . 2_765 ? O15 La2 O2 139.5(3) . 2_765 ? O13 La2 O2 92.8(3) . 2_765 ? O10 La2 O12 80.9(3) 2_765 . ? O7 La2 O12 159.6(3) . . ? O14 La2 O12 63.3(3) . . ? O15 La2 O12 97.2(3) . . ? O13 La2 O12 131.3(3) . . ? O2 La2 O12 61.0(2) 2_765 . ? O10 La2 O1 68.7(3) 2_765 2_765 ? O7 La2 O1 79.1(3) . 2_765 ? O14 La2 O1 102.7(3) . 2_765 ? O15 La2 O1 146.0(3) . 2_765 ? O13 La2 O1 69.9(3) . 2_765 ? O2 La2 O1 49.3(2) 2_765 2_765 ? O12 La2 O1 108.5(2) . 2_765 ? O10 La2 O9 74.0(3) 2_765 . ? O7 La2 O9 109.9(3) . . ? O14 La2 O9 97.0(3) . . ? O15 La2 O9 73.1(3) . . ? O13 La2 O9 149.4(3) . . ? O2 La2 O9 109.0(2) 2_765 . ? O12 La2 O9 52.1(2) . . ? O1 La2 O9 140.6(3) 2_765 . ? O10 La2 O8 72.6(3) 2_765 . ? O7 La2 O8 49.3(3) . . ? O14 La2 O8 138.0(3) . . ? O15 La2 O8 70.5(3) . . ? O13 La2 O8 110.9(3) . . ? O2 La2 O8 147.2(3) 2_765 . ? O12 La2 O8 112.0(2) . . ? O1 La2 O8 117.0(2) 2_765 . ? O9 La2 O8 60.5(2) . . ? O10 La2 C18 79.9(3) 2_765 . ? O7 La2 C18 24.2(3) . . ? O14 La2 C18 140.4(3) . . ? O15 La2 C18 74.2(3) . . ? O13 La2 C18 88.2(3) . . ? O2 La2 C18 145.3(3) 2_765 . ? O12 La2 C18 137.2(3) . . ? O1 La2 C18 99.4(3) 2_765 . ? O9 La2 C18 85.8(3) . . ? O8 La2 C18 25.3(3) . . ? O10 La2 C1 72.9(3) 2_765 2_765 ? O7 La2 C1 103.3(3) . 2_765 ? O14 La2 C1 84.5(3) . 2_765 ? O15 La2 C1 147.9(3) . 2_765 ? O13 La2 C1 77.5(3) . 2_765 ? O2 La2 C1 25.4(3) 2_765 2_765 ? O12 La2 C1 86.2(3) . 2_765 ? O1 La2 C1 24.3(3) 2_765 2_765 ? O9 La2 C1 129.9(3) . 2_765 ? O8 La2 C1 137.5(3) . 2_765 ? C18 La2 C1 123.4(3) . 2_765 ? C5 N1 C4 105.6(10) . . ? C5 N1 H1 114(9) . . ? C4 N1 H1 139(10) . . ? C5 N2 C6 105.3(11) . . ? C14 N4 C13 107.5(10) . . ? C14 N4 H4 126.3 . . ? C13 N4 H4 126.3 . . ? C14 N3 C15 103.4(10) . . ? C1 O1 La2 94.8(7) . 2_765 ? C1 O2 La1 136.8(7) . . ? C1 O2 La2 96.3(6) . 2_765 ? La1 O2 La2 115.7(3) . 2_765 ? C9 O3 La1 127.8(7) . . ? C9 O4 La1 135.6(8) . 2_755 ? C10 O5 La1 123.8(7) . . ? C10 O6 La1 145.7(8) . 2_655 ? C18 O7 La2 99.4(7) . . ? C18 O8 La1 149.7(8) . . ? C18 O8 La2 90.2(7) . . ? La1 O8 La2 112.9(3) . . ? La2 O15 H15A 108.7 . . ? La2 O15 H15B 113.1 . . ? H15A O15 H15B 109.0 . . ? La2 O13 H13B 111.5 . . ? La2 O13 H13A 111.5 . . ? H13B O13 H13A 109.4 . . ? La2 O14 H14A 119.2 . . ? La2 O14 H14B 95.3 . . ? H14A O14 H14B 119.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.89(15) 1.90(15) 2.792(14) 176(13) 2_654 O14 H14B O3 0.85 2.26 2.919(13) 134.9 1_565 O14 H14A O5 0.85 2.26 2.803(12) 122.1 1_565 O13 H13A N2 0.85 2.53 3.318(16) 154.4 2_655 O13 H13B N3 0.85 1.94 2.758(13) 161.5 2_766 O15 H15B O11 0.85 2.20 2.971(14) 150.7 2_665 N4 H4 N2 0.86 2.11 2.920(15) 156.6 2_645 O15 H15A O8 0.85 2.63 3.041(13) 111.0 . O14 H14B O12 0.85 2.13 2.729(13) 127.2 . _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.126 _refine_diff_density_min -1.047 _refine_diff_density_rms 0.242 # Attachment 'Pr1.cif' data_Pr _database_code_depnum_ccdc_archive 'CCDC 734654' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 N4 O15 Pr2 S' _chemical_formula_sum 'C18 H14 N4 O15 Pr2 S' _chemical_formula_weight 840.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pr Pr -0.2180 2.8214 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5697(13) _cell_length_b 9.9532(13) _cell_length_c 14.288(2) _cell_angle_alpha 91.200(2) _cell_angle_beta 107.652(2) _cell_angle_gamma 118.4730(10) _cell_volume 1117.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3794 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 24.31 _exptl_crystal_description sheet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 4.495 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.416 _exptl_absorpt_correction_T_max 0.510 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 area-detector diffractometer' _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 5823 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.20 _reflns_number_total 3926 _reflns_number_gt 3388 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material 'SHELXTL(Bruker, 2002)' _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^)+(0.0284P)^2^+14.4362P] 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 3926 _refine_ls_number_parameters 361 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.044 _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 0.7858(10) 0.1240(9) 0.2559(6) 0.0138(16) Uani 1 1 d . . . C2 C 0.6646(10) -0.0448(9) 0.2103(6) 0.0145(16) Uani 1 1 d . . . C3 C 0.5426(10) -0.0813(9) 0.1158(6) 0.0159(16) Uani 1 1 d . . . H3 H 0.5275 -0.0048 0.0860 0.019 Uiso 1 1 calc R . . C4 C 0.4445(10) -0.2371(10) 0.0680(6) 0.0174(17) Uani 1 1 d . . . C5 C 0.2759(12) -0.4636(11) -0.0346(7) 0.028(2) Uani 1 1 d . . . H5 H 0.1950 -0.5386 -0.0918 0.034 Uiso 1 1 calc R . . C6 C 0.4652(10) -0.3519(10) 0.1116(6) 0.0204(18) Uani 1 1 d . . . C7 C 0.5896(10) -0.3152(10) 0.2075(6) 0.0191(18) Uani 1 1 d . . . H7 H 0.6053 -0.3921 0.2364 0.023 Uiso 1 1 calc R . . C8 C 0.6871(10) -0.1609(9) 0.2567(6) 0.0155(16) Uani 1 1 d . . . C9 C 0.8195(9) -0.1285(8) 0.3562(5) 0.0085(14) Uani 1 1 d U . . C10 C 0.5867(8) -0.0405(9) 0.6440(5) 0.0097(15) Uani 1 1 d . . . C11 C 0.6834(9) -0.0004(9) 0.7543(6) 0.0140(16) Uani 1 1 d . . . C12 C 0.6477(11) -0.1242(10) 0.8032(6) 0.0186(17) Uani 1 1 d . . . H12 H 0.5714 -0.2265 0.7686 0.022 Uiso 1 1 calc R . . C13 C 0.7304(10) -0.0898(10) 0.9065(6) 0.0174(17) Uani 1 1 d . . . C14 C 0.8429(11) -0.0843(10) 1.0654(6) 0.0209(18) Uani 1 1 d . . . H14 H 0.8670 -0.1195 1.1248 0.025 Uiso 1 1 calc R . . C15 C 0.8392(10) 0.0649(10) 0.9596(6) 0.0149(16) Uani 1 1 d . . . C16 C 0.8714(10) 0.1894(9) 0.9102(6) 0.0165(17) Uani 1 1 d . . . H16 H 0.9419 0.2918 0.9455 0.020 Uiso 1 1 calc R . . C17 C 0.7953(10) 0.1560(10) 0.8066(6) 0.0166(17) Uani 1 1 d . . . C18 C 0.8409(10) 0.2867(10) 0.7531(6) 0.0169(17) Uani 1 1 d . . . N1 N 0.3223(9) -0.3112(8) -0.0262(5) 0.0239(16) Uani 1 1 d . . . H1 H 0.2834 -0.2688 -0.0707 0.029 Uiso 1 1 calc R . . N2 N 0.3554(10) -0.4950(9) 0.0451(6) 0.0328(19) Uani 1 1 d . . . N3 N 0.9095(9) 0.0636(8) 1.0609(5) 0.0178(15) Uani 1 1 d . . . N4 N 0.7366(9) -0.1807(9) 0.9766(5) 0.0205(15) Uani 1 1 d . . . H4 H 0.6824 -0.2809 0.9657 0.025 Uiso 1 1 calc R . . O1 O 0.8120(8) 0.2251(7) 0.2018(4) 0.0219(13) Uani 1 1 d . . . O2 O 0.8742(7) 0.1631(6) 0.3489(4) 0.0154(12) Uani 1 1 d . . . O3 O 0.7899(7) -0.1045(7) 0.4354(4) 0.0202(13) Uani 1 1 d . . . O4 O 0.9490(7) -0.1294(7) 0.3582(4) 0.0246(14) Uani 1 1 d . . . O5 O 0.6477(7) -0.0652(7) 0.5835(4) 0.0226(13) Uani 1 1 d . . . O6 O 0.4494(7) -0.0382(7) 0.6161(4) 0.0258(14) Uani 1 1 d . . . O8 O 0.8108(7) 0.2646(7) 0.6592(4) 0.0206(13) Uani 1 1 d . . . O7 O 0.9138(8) 0.4254(7) 0.8014(4) 0.0257(14) Uani 1 1 d . . . O9 O 0.7774(7) 0.3673(7) 0.4868(4) 0.0214(13) Uani 1 1 d . . . O10 O 0.8589(8) 0.4616(8) 0.3449(4) 0.0252(14) Uani 1 1 d . . . O11 O 0.6160(7) 0.4561(7) 0.3660(4) 0.0217(13) Uani 1 1 d . . . O12 O 0.9000(7) 0.6361(7) 0.4835(4) 0.0203(13) Uani 1 1 d . . . O13 O 0.8416(8) 0.6704(8) 0.7961(5) 0.0317(15) Uani 1 1 d . . . H13C H 0.8073 0.6012 0.8307 0.038 Uiso 1 1 d R . . H13B H 0.9294 0.7527 0.8343 0.038 Uiso 1 1 d R . . O14 O 0.7568(10) 0.7162(9) 0.5955(5) 0.0401(18) Uani 1 1 d . . . H14B H 0.7836 0.7596 0.5482 0.048 Uiso 1 1 d R . . H14A H 0.7834 0.7807 0.6467 0.048 Uiso 1 1 d R . . O15 O 0.5842(8) 0.3964(8) 0.6168(6) 0.0389(17) Uani 1 1 d . . . H15A H 0.5277 0.4004 0.5592 0.047 Uiso 1 1 d R . . H15B H 0.5805 0.4464 0.6641 0.047 Uiso 1 1 d R . . Pr1 Pr 0.82305(5) 0.13701(5) 0.51085(3) 0.01285(13) Uani 1 1 d . . . Pr2 Pr 0.90053(5) 0.56440(5) 0.65929(3) 0.01434(13) Uani 1 1 d . . . S1 S 0.7833(2) 0.4778(2) 0.41654(14) 0.0132(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.018(4) 0.010(4) 0.016(4) 0.001(3) 0.006(3) 0.010(3) C2 0.019(4) 0.013(4) 0.016(4) 0.005(3) 0.011(3) 0.008(3) C3 0.017(4) 0.012(4) 0.013(4) 0.002(3) 0.002(3) 0.005(3) C4 0.020(4) 0.021(5) 0.012(4) 0.003(3) 0.004(3) 0.012(4) C5 0.028(5) 0.020(5) 0.021(5) -0.001(4) -0.004(4) 0.009(4) C6 0.021(4) 0.017(4) 0.017(4) 0.004(3) 0.003(3) 0.007(4) C7 0.020(4) 0.012(4) 0.020(4) 0.006(3) -0.002(3) 0.009(4) C8 0.016(4) 0.015(4) 0.012(4) 0.001(3) 0.004(3) 0.006(3) C9 0.008(2) 0.007(3) 0.009(3) 0.003(2) 0.0012(19) 0.003(2) C10 0.004(3) 0.011(4) 0.008(4) -0.004(3) -0.002(3) 0.002(3) C11 0.014(4) 0.014(4) 0.014(4) 0.000(3) 0.003(3) 0.008(3) C12 0.025(4) 0.015(4) 0.015(4) 0.003(3) 0.010(3) 0.007(4) C13 0.020(4) 0.015(4) 0.021(4) 0.007(3) 0.010(3) 0.010(4) C14 0.028(4) 0.027(5) 0.018(4) 0.010(4) 0.012(4) 0.019(4) C15 0.018(4) 0.019(4) 0.012(4) 0.002(3) 0.005(3) 0.013(4) C16 0.018(4) 0.011(4) 0.022(4) 0.004(3) 0.008(3) 0.008(3) C17 0.018(4) 0.022(5) 0.016(4) 0.003(3) 0.005(3) 0.015(4) C18 0.016(4) 0.031(5) 0.010(4) 0.007(3) 0.003(3) 0.017(4) N1 0.023(4) 0.018(4) 0.020(4) 0.002(3) 0.000(3) 0.007(3) N2 0.034(4) 0.016(4) 0.029(4) 0.004(3) -0.001(4) 0.005(4) N3 0.025(4) 0.020(4) 0.010(3) 0.002(3) 0.006(3) 0.013(3) N4 0.020(3) 0.019(4) 0.024(4) 0.007(3) 0.010(3) 0.009(3) O1 0.032(3) 0.016(3) 0.012(3) 0.003(2) 0.008(2) 0.008(3) O2 0.020(3) 0.011(3) 0.008(3) 0.000(2) 0.000(2) 0.006(2) O3 0.029(3) 0.017(3) 0.015(3) 0.000(2) 0.007(2) 0.012(3) O4 0.017(3) 0.032(4) 0.020(3) -0.003(3) 0.001(2) 0.013(3) O5 0.029(3) 0.019(3) 0.023(3) 0.004(3) 0.014(3) 0.011(3) O6 0.024(3) 0.030(4) 0.022(3) 0.003(3) 0.006(3) 0.015(3) O8 0.030(3) 0.018(3) 0.015(3) 0.007(2) 0.011(2) 0.012(3) O7 0.044(4) 0.012(3) 0.016(3) 0.004(2) 0.008(3) 0.012(3) O9 0.026(3) 0.019(3) 0.018(3) 0.004(2) 0.009(2) 0.010(3) O10 0.030(3) 0.034(4) 0.019(3) 0.004(3) 0.009(3) 0.021(3) O11 0.016(3) 0.025(3) 0.021(3) 0.001(3) -0.001(2) 0.011(3) O12 0.020(3) 0.016(3) 0.017(3) -0.003(2) 0.002(2) 0.006(3) O13 0.033(4) 0.027(4) 0.030(4) -0.006(3) 0.011(3) 0.012(3) O14 0.063(5) 0.049(5) 0.044(4) 0.025(4) 0.034(4) 0.046(4) O15 0.025(3) 0.034(4) 0.051(5) -0.002(3) 0.013(3) 0.010(3) Pr1 0.0148(2) 0.0130(2) 0.0114(2) 0.00190(17) 0.00418(17) 0.00777(19) Pr2 0.0172(2) 0.0128(2) 0.0139(2) 0.00204(17) 0.00587(17) 0.0081(2) S1 0.0154(9) 0.0125(10) 0.0129(9) 0.0009(7) 0.0038(7) 0.0088(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.258(10) . ? C1 O2 1.272(9) . ? C1 C2 1.493(11) . ? C1 Pr2 2.976(8) 2_766 ? C2 C3 1.392(11) . ? C2 C8 1.415(11) . ? C3 C4 1.390(11) . ? C3 H3 0.9300 . ? C4 N1 1.380(10) . ? C4 C6 1.380(12) . ? C5 N2 1.300(12) . ? C5 N1 1.353(12) . ? C5 H5 0.9300 . ? C6 N2 1.395(11) . ? C6 C7 1.415(11) . ? C7 C8 1.383(11) . ? C7 H7 0.9300 . ? C8 C9 1.494(10) . ? C9 O4 1.236(9) . ? C9 O3 1.290(9) . ? C10 O5 1.259(9) . ? C10 O6 1.264(9) . ? C10 C11 1.495(10) . ? C11 C12 1.380(11) . ? C11 C17 1.416(11) . ? C12 C13 1.390(11) . ? C12 H12 0.9300 . ? C13 N4 1.371(11) . ? C13 C15 1.405(12) . ? C14 N3 1.308(11) . ? C14 N4 1.342(11) . ? C14 H14 0.9300 . ? C15 C16 1.389(11) . ? C15 N3 1.403(10) . ? C16 C17 1.389(11) . ? C16 H16 0.9300 . ? C17 C18 1.473(12) . ? C18 O7 1.272(10) . ? C18 O8 1.274(9) . ? C18 Pr2 2.979(8) . ? N1 H1 0.8600 . ? N4 H4 0.8600 . ? O1 Pr2 2.630(6) 2_766 ? O2 Pr1 2.500(5) . ? O2 Pr2 2.571(5) 2_766 ? O3 Pr1 2.449(5) . ? O4 Pr1 2.440(6) 2_756 ? O5 Pr1 2.422(6) . ? O6 Pr1 2.381(6) 2_656 ? O8 Pr1 2.510(6) . ? O8 Pr2 2.683(6) . ? O7 Pr2 2.486(6) . ? O9 S1 1.498(6) . ? O9 Pr1 2.541(6) . ? O9 Pr2 2.673(6) . ? O10 S1 1.466(6) . ? O10 Pr2 2.454(6) 2_766 ? O11 S1 1.447(5) . ? O12 S1 1.502(6) . ? O12 Pr1 2.507(6) 2_766 ? O12 Pr2 2.624(6) . ? O13 Pr2 2.530(6) . ? O13 H13C 0.8500 . ? O13 H13B 0.8500 . ? O14 Pr2 2.506(6) . ? O14 H14B 0.8499 . ? O14 H14A 0.8501 . ? O15 Pr2 2.519(6) . ? O15 H15A 0.8500 . ? O15 H15B 0.8500 . ? Pr1 O6 2.381(6) 2_656 ? Pr1 O4 2.440(6) 2_756 ? Pr1 O12 2.507(6) 2_766 ? Pr2 O10 2.454(6) 2_766 ? Pr2 O2 2.571(5) 2_766 ? Pr2 O1 2.630(6) 2_766 ? Pr2 C1 2.976(8) 2_766 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 120.0(7) . . ? O1 C1 C2 120.7(7) . . ? O2 C1 C2 119.0(7) . . ? O1 C1 Pr2 61.9(4) . 2_766 ? O2 C1 Pr2 59.3(4) . 2_766 ? C2 C1 Pr2 163.4(5) . 2_766 ? C3 C2 C8 121.7(7) . . ? C3 C2 C1 117.2(7) . . ? C8 C2 C1 120.7(7) . . ? C4 C3 C2 117.1(7) . . ? C4 C3 H3 121.5 . . ? C2 C3 H3 121.5 . . ? N1 C4 C6 105.7(7) . . ? N1 C4 C3 132.1(8) . . ? C6 C4 C3 122.1(7) . . ? N2 C5 N1 113.4(8) . . ? N2 C5 H5 123.3 . . ? N1 C5 H5 123.3 . . ? C4 C6 N2 109.4(7) . . ? C4 C6 C7 121.0(8) . . ? N2 C6 C7 129.4(8) . . ? C8 C7 C6 117.7(7) . . ? C8 C7 H7 121.2 . . ? C6 C7 H7 121.2 . . ? C7 C8 C2 120.4(7) . . ? C7 C8 C9 115.3(7) . . ? C2 C8 C9 124.2(7) . . ? O4 C9 O3 123.8(7) . . ? O4 C9 C8 118.3(7) . . ? O3 C9 C8 117.9(6) . . ? O5 C10 O6 122.9(7) . . ? O5 C10 C11 120.1(6) . . ? O6 C10 C11 116.9(6) . . ? C12 C11 C17 121.9(7) . . ? C12 C11 C10 116.0(7) . . ? C17 C11 C10 121.9(7) . . ? C11 C12 C13 117.2(8) . . ? C11 C12 H12 121.4 . . ? C13 C12 H12 121.4 . . ? N4 C13 C12 133.0(8) . . ? N4 C13 C15 105.5(7) . . ? C12 C13 C15 121.5(7) . . ? N3 C14 N4 113.9(7) . . ? N3 C14 H14 123.1 . . ? N4 C14 H14 123.1 . . ? C16 C15 N3 130.0(7) . . ? C16 C15 C13 121.0(7) . . ? N3 C15 C13 108.7(7) . . ? C17 C16 C15 117.9(8) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C16 C17 C11 120.3(8) . . ? C16 C17 C18 118.2(7) . . ? C11 C17 C18 121.4(7) . . ? O7 C18 O8 118.8(7) . . ? O7 C18 C17 119.6(7) . . ? O8 C18 C17 121.5(8) . . ? O7 C18 Pr2 55.3(4) . . ? O8 C18 Pr2 64.2(4) . . ? C17 C18 Pr2 170.6(5) . . ? C5 N1 C4 106.5(7) . . ? C5 N1 H1 126.8 . . ? C4 N1 H1 126.8 . . ? C5 N2 C6 104.9(8) . . ? C14 N3 C15 104.6(7) . . ? C14 N4 C13 107.3(7) . . ? C14 N4 H4 126.3 . . ? C13 N4 H4 126.3 . . ? C1 O1 Pr2 93.1(5) . 2_766 ? C1 O2 Pr1 137.7(5) . . ? C1 O2 Pr2 95.5(5) . 2_766 ? Pr1 O2 Pr2 115.75(19) . 2_766 ? C9 O3 Pr1 127.3(5) . . ? C9 O4 Pr1 133.9(5) . 2_756 ? C10 O5 Pr1 123.3(5) . . ? C10 O6 Pr1 146.0(5) . 2_656 ? C18 O8 Pr1 149.1(5) . . ? C18 O8 Pr2 90.5(5) . . ? Pr1 O8 Pr2 113.2(2) . . ? C18 O7 Pr2 99.8(5) . . ? S1 O9 Pr1 140.5(3) . . ? S1 O9 Pr2 98.9(3) . . ? Pr1 O9 Pr2 112.5(2) . . ? S1 O10 Pr2 140.0(3) . 2_766 ? S1 O12 Pr1 132.8(3) . 2_766 ? S1 O12 Pr2 100.8(3) . . ? Pr1 O12 Pr2 113.6(2) 2_766 . ? Pr2 O13 H13C 109.0 . . ? Pr2 O13 H13B 112.0 . . ? H13C O13 H13B 109.2 . . ? Pr2 O14 H14B 113.1 . . ? Pr2 O14 H14A 105.1 . . ? H14B O14 H14A 113.2 . . ? Pr2 O15 H15A 112.3 . . ? Pr2 O15 H15B 95.3 . . ? H15A O15 H15B 112.7 . . ? O6 Pr1 O5 79.7(2) 2_656 . ? O6 Pr1 O4 157.4(2) 2_656 2_756 ? O5 Pr1 O4 82.1(2) . 2_756 ? O6 Pr1 O3 81.4(2) 2_656 . ? O5 Pr1 O3 74.53(19) . . ? O4 Pr1 O3 80.88(19) 2_756 . ? O6 Pr1 O2 74.20(19) 2_656 . ? O5 Pr1 O2 138.03(18) . . ? O4 Pr1 O2 112.09(19) 2_756 . ? O3 Pr1 O2 69.54(18) . . ? O6 Pr1 O12 127.3(2) 2_656 2_766 ? O5 Pr1 O12 152.74(19) . 2_766 ? O4 Pr1 O12 72.3(2) 2_756 2_766 ? O3 Pr1 O12 109.50(19) . 2_766 ? O2 Pr1 O12 63.48(17) . 2_766 ? O6 Pr1 O8 105.1(2) 2_656 . ? O5 Pr1 O8 71.56(19) . . ? O4 Pr1 O8 81.49(19) 2_756 . ? O3 Pr1 O8 143.50(19) . . ? O2 Pr1 O8 146.97(18) . . ? O12 Pr1 O8 95.06(19) 2_766 . ? O6 Pr1 O9 73.5(2) 2_656 . ? O5 Pr1 O9 118.34(19) . . ? O4 Pr1 O9 127.59(19) 2_756 . ? O3 Pr1 O9 148.32(18) . . ? O2 Pr1 O9 85.01(18) . . ? O12 Pr1 O9 72.97(19) 2_766 . ? O8 Pr1 O9 63.93(18) . . ? O10 Pr2 O7 83.8(2) 2_766 . ? O10 Pr2 O14 140.1(2) 2_766 . ? O7 Pr2 O14 133.9(2) . . ? O10 Pr2 O15 139.1(2) 2_766 . ? O7 Pr2 O15 83.2(2) . . ? O14 Pr2 O15 69.9(2) . . ? O10 Pr2 O13 133.6(2) 2_766 . ? O7 Pr2 O13 68.7(2) . . ? O14 Pr2 O13 68.7(2) . . ? O15 Pr2 O13 75.4(2) . . ? O10 Pr2 O2 74.5(2) 2_766 2_766 ? O7 Pr2 O2 127.61(18) . 2_766 ? O14 Pr2 O2 71.3(2) . 2_766 ? O15 Pr2 O2 141.1(2) . 2_766 ? O13 Pr2 O2 93.0(2) . 2_766 ? O10 Pr2 O12 81.85(19) 2_766 . ? O7 Pr2 O12 160.13(19) . . ? O14 Pr2 O12 64.0(2) . . ? O15 Pr2 O12 98.8(2) . . ? O13 Pr2 O12 131.0(2) . . ? O2 Pr2 O12 60.93(17) 2_766 . ? O10 Pr2 O1 68.25(19) 2_766 2_766 ? O7 Pr2 O1 77.93(19) . 2_766 ? O14 Pr2 O1 102.9(2) . 2_766 ? O15 Pr2 O1 144.5(2) . 2_766 ? O13 Pr2 O1 69.8(2) . 2_766 ? O2 Pr2 O1 49.82(17) 2_766 2_766 ? O12 Pr2 O1 109.08(17) . 2_766 ? O10 Pr2 O9 75.56(19) 2_766 . ? O7 Pr2 O9 109.92(18) . . ? O14 Pr2 O9 97.3(2) . . ? O15 Pr2 O9 72.9(2) . . ? O13 Pr2 O9 148.18(19) . . ? O2 Pr2 O9 109.81(17) 2_766 . ? O12 Pr2 O9 52.98(18) . . ? O1 Pr2 O9 141.98(18) 2_766 . ? O10 Pr2 O8 72.8(2) 2_766 . ? O7 Pr2 O8 50.00(18) . . ? O14 Pr2 O8 137.5(2) . . ? O15 Pr2 O8 69.2(2) . . ? O13 Pr2 O8 110.7(2) . . ? O2 Pr2 O8 147.31(17) 2_766 . ? O12 Pr2 O8 112.09(17) . . ? O1 Pr2 O8 116.99(18) 2_766 . ? O9 Pr2 O8 59.92(17) . . ? O10 Pr2 C1 72.3(2) 2_766 2_766 ? O7 Pr2 C1 102.9(2) . 2_766 ? O14 Pr2 C1 84.8(2) . 2_766 ? O15 Pr2 C1 148.5(2) . 2_766 ? O13 Pr2 C1 78.1(2) . 2_766 ? O2 Pr2 C1 25.17(19) 2_766 2_766 ? O12 Pr2 C1 85.80(19) . 2_766 ? O1 Pr2 C1 24.96(19) 2_766 2_766 ? O9 Pr2 C1 130.57(19) . 2_766 ? O8 Pr2 C1 137.65(19) . 2_766 ? O10 Pr2 C18 79.4(2) 2_766 . ? O7 Pr2 C18 24.9(2) . . ? O14 Pr2 C18 139.8(2) . . ? O15 Pr2 C18 72.7(2) . . ? O13 Pr2 C18 88.3(2) . . ? O2 Pr2 C18 145.13(19) 2_766 . ? O12 Pr2 C18 137.3(2) . . ? O1 Pr2 C18 98.98(19) 2_766 . ? O9 Pr2 C18 85.2(2) . . ? O8 Pr2 C18 25.31(19) . . ? C1 Pr2 C18 123.5(2) 2_766 . ? O11 S1 O10 111.6(3) . . ? O11 S1 O9 111.1(4) . . ? O10 S1 O9 110.6(3) . . ? O11 S1 O12 110.6(3) . . ? O10 S1 O12 108.8(4) . . ? O9 S1 O12 103.9(3) . . ? O11 S1 Pr2 111.8(2) . . ? O10 S1 Pr2 136.5(2) . . ? O9 S1 Pr2 54.1(2) . . ? O12 S1 Pr2 52.2(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.86 1.98 2.804(9) 161.5 2_655 N4 H4 N2 0.86 2.08 2.894(11) 158.5 2_646 O13 H13B N3 0.85 1.94 2.769(9) 165.2 2_767 O14 H14B O3 0.85 2.12 2.931(9) 159.1 1_565 O15 H15B O11 0.85 2.44 2.973(9) 121.8 2_666 O13 H13C N2 0.85 2.62 3.371(11) 147.7 2_656 O15 H15B O13 0.85 2.53 3.089(9) 123.8 . O15 H15A O14 0.85 2.76 2.878(10) 89.2 . _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 2.252 _refine_diff_density_min -1.690 _refine_diff_density_rms 0.202 # Attachment 'Tb.cif' data_Tb _database_code_depnum_ccdc_archive 'CCDC 734655' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C18 H8 N4 O12 S Tb2), H4 O2' _chemical_formula_sum 'C36 H20 N8 O26 S2 Tb4' _chemical_formula_weight 1680.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5378(8) _cell_length_b 6.6828(5) _cell_length_c 16.1310(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.7490(10) _cell_angle_gamma 90.00 _cell_volume 1021.05(14) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2372 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 25.34 _exptl_crystal_description cubic _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.733 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 7.061 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.218 _exptl_absorpt_correction_T_max 0.301 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 area-detector diffractometer' _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 5104 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.10 _reflns_number_total 1805 _reflns_number_gt 1707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material 'SHELXTL(Bruker, 2002)' _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^)+(0.0207P)^2^+64.8453P] 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 1805 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 0.59178(6) 0.42027(9) 0.39896(3) 0.0087(2) Uani 1 1 d . . . S1 S 0.4080(6) 0.0782(9) 0.5225(4) 0.0118(12) Uani 0.50 1 d P . . O1 O 0.7980(12) 0.3814(18) 0.4964(7) 0.038(3) Uani 1 1 d . . . O2 O 0.6238(10) 0.4776(15) 0.5559(6) 0.021(2) Uani 1 1 d . . . O3 O 0.5677(9) 0.5315(17) 0.7115(5) 0.024(2) Uani 1 1 d . . . O4 O 0.6478(10) 0.3446(16) 0.8175(5) 0.023(2) Uani 1 1 d . . . O5 O 0.493(2) 0.129(3) 0.4491(12) 0.026(5) Uani 0.50 1 d P . . O6 O 0.3954(14) 0.228(2) 0.5842(7) 0.044(3) Uani 1 1 d . . . O7 O 0.259(2) 0.031(4) 0.4977(12) 0.029(5) Uani 0.50 1 d P . . O8 O 0.054(2) 0.017(4) 0.4934(15) 0.044(6) Uani 0.50 1 d P . . H8A H 0.0053 0.1050 0.4652 0.066 Uiso 0.50 1 d PR . . H8B H 0.0189 -0.0981 0.4824 0.066 Uiso 0.50 1 d PR . . N2 N 1.1789(11) 0.4392(18) 0.8308(7) 0.018(2) Uani 1 1 d . . . H2 H 1.1871 0.4336 0.8845 0.022 Uiso 1 1 calc R . . N1 N 1.2407(11) 0.4550(18) 0.7002(6) 0.015(2) Uani 1 1 d . . . C1 C 0.7486(13) 0.4335(19) 0.5621(7) 0.014(3) Uani 1 1 d . . . C2 C 0.8481(13) 0.440(2) 0.6414(7) 0.014(3) Uani 1 1 d . . . C3 C 0.9896(13) 0.443(2) 0.6285(8) 0.014(3) Uani 1 1 d . . . H3 H 1.0145 0.4427 0.5744 0.017 Uiso 1 1 calc R . . C4 C 1.0937(13) 0.4460(18) 0.6961(8) 0.011(2) Uani 1 1 d . . . C5 C 1.0557(13) 0.437(2) 0.7768(8) 0.015(3) Uani 1 1 d . . . C6 C 0.9155(13) 0.431(2) 0.7916(8) 0.016(3) Uani 1 1 d . . . H6 H 0.8921 0.4243 0.8459 0.020 Uiso 1 1 calc R . . C7 C 0.8128(13) 0.4343(19) 0.7257(8) 0.013(3) Uani 1 1 d . . . C8 C 0.6639(13) 0.4337(19) 0.7515(8) 0.014(3) Uani 1 1 d . . . C9 C 1.2885(16) 0.452(2) 0.7799(9) 0.023(3) Uani 1 1 d . . . H9 H 1.3838 0.4580 0.8003 0.028 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 Tb1 0.0086(3) 0.0114(3) 0.0064(3) -0.0009(2) 0.0025(2) 0.0004(2) S1 0.018(3) 0.012(3) 0.007(3) 0.000(2) 0.006(2) -0.003(2) O1 0.042(7) 0.037(7) 0.032(6) -0.027(5) -0.001(5) 0.000(5) O2 0.023(5) 0.024(5) 0.016(5) -0.011(4) -0.002(4) 0.000(4) O3 0.012(4) 0.048(7) 0.011(4) 0.002(4) 0.003(4) 0.001(5) O4 0.028(5) 0.030(6) 0.010(4) 0.003(4) 0.002(4) 0.001(4) O5 0.030(11) 0.030(12) 0.020(10) 0.003(9) 0.006(8) 0.000(9) O6 0.060(8) 0.046(8) 0.025(6) -0.008(6) 0.002(5) 0.000(6) O7 0.020(10) 0.049(14) 0.018(10) 0.001(10) -0.001(8) -0.011(10) O8 0.041(14) 0.056(16) 0.033(12) -0.028(12) 0.000(12) 0.000(14) N2 0.013(5) 0.031(7) 0.012(5) -0.002(5) 0.010(4) 0.001(5) N1 0.010(5) 0.028(6) 0.008(5) 0.003(5) 0.004(4) -0.002(5) C1 0.017(7) 0.014(6) 0.011(6) -0.001(5) 0.003(5) -0.001(5) C2 0.013(6) 0.021(7) 0.008(6) -0.002(5) 0.007(5) -0.002(5) C3 0.012(6) 0.020(7) 0.012(6) 0.005(5) 0.008(5) -0.001(5) C4 0.012(6) 0.009(6) 0.014(6) 0.003(5) 0.006(5) -0.002(5) C5 0.015(6) 0.017(7) 0.011(6) 0.002(5) -0.002(5) 0.005(5) C6 0.016(6) 0.020(7) 0.015(6) 0.000(5) 0.008(5) 0.000(5) C7 0.014(6) 0.014(6) 0.012(6) 0.003(5) 0.001(5) 0.001(5) C8 0.014(6) 0.015(7) 0.015(6) -0.003(5) 0.004(5) -0.002(5) C9 0.026(7) 0.021(7) 0.022(7) 0.002(6) 0.003(6) 0.000(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tb1 O3 2.226(9) 3_666 ? Tb1 O4 2.304(10) 4_565 ? Tb1 O5 2.35(2) . ? Tb1 O2 2.361(9) 3_666 ? Tb1 O6 2.368(13) 3_666 ? Tb1 O1 2.383(12) . ? Tb1 N1 2.531(10) 3_766 ? Tb1 O2 2.542(9) . ? Tb1 C1 2.872(12) . ? S1 O6 1.427(13) . ? S1 O7 1.46(2) . ? S1 O5 1.547(19) . ? S1 O5 1.71(2) 3_656 ? S1 S1 2.235(12) 3_656 ? O1 C1 1.260(16) . ? O2 C1 1.220(16) . ? O2 Tb1 2.361(9) 3_666 ? O3 C8 1.244(16) . ? O3 Tb1 2.226(9) 3_666 ? O4 C8 1.245(16) . ? O4 Tb1 2.304(10) 4_566 ? O5 S1 1.71(2) 3_656 ? O6 Tb1 2.368(13) 3_666 ? O8 O8 1.10(4) 3_556 ? O8 H8A 0.8500 . ? O8 H8B 0.8500 . ? N2 C5 1.378(16) . ? N2 C9 1.406(17) . ? N2 H2 0.8600 . ? N1 C9 1.314(18) . ? N1 C4 1.397(16) . ? N1 Tb1 2.531(10) 3_766 ? C1 C2 1.500(17) . ? C2 C3 1.390(17) . ? C2 C7 1.441(16) . ? C3 C4 1.387(18) . ? C3 H3 0.9300 . ? C4 C5 1.393(17) . ? C5 C6 1.387(18) . ? C6 C7 1.358(18) . ? C6 H6 0.9300 . ? C7 C8 1.525(17) . ? C9 H9 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 O3 Tb1 O4 80.6(4) 3_666 4_565 ? O3 Tb1 O5 97.5(6) 3_666 . ? O4 Tb1 O5 72.0(5) 4_565 . ? O3 Tb1 O2 70.6(3) 3_666 3_666 ? O4 Tb1 O2 131.8(3) 4_565 3_666 ? O5 Tb1 O2 74.4(6) . 3_666 ? O3 Tb1 O6 88.2(4) 3_666 3_666 ? O4 Tb1 O6 144.6(4) 4_565 3_666 ? O5 Tb1 O6 143.2(6) . 3_666 ? O2 Tb1 O6 73.3(4) 3_666 3_666 ? O3 Tb1 O1 167.7(4) 3_666 . ? O4 Tb1 O1 93.6(3) 4_565 . ? O5 Tb1 O1 91.0(6) . . ? O2 Tb1 O1 120.6(3) 3_666 . ? O6 Tb1 O1 90.3(4) 3_666 . ? O3 Tb1 N1 82.5(3) 3_666 3_766 ? O4 Tb1 N1 71.7(4) 4_565 3_766 ? O5 Tb1 N1 143.2(6) . 3_766 ? O2 Tb1 N1 137.5(4) 3_666 3_766 ? O6 Tb1 N1 73.6(4) 3_666 3_766 ? O1 Tb1 N1 85.4(4) . 3_766 ? O3 Tb1 O2 140.0(3) 3_666 . ? O4 Tb1 O2 132.4(3) 4_565 . ? O5 Tb1 O2 77.8(5) . . ? O2 Tb1 O2 69.9(4) 3_666 . ? O6 Tb1 O2 74.8(4) 3_666 . ? O1 Tb1 O2 50.7(3) . . ? N1 Tb1 O2 124.6(3) 3_766 . ? O3 Tb1 C1 164.3(4) 3_666 . ? O4 Tb1 C1 114.5(3) 4_565 . ? O5 Tb1 C1 84.1(6) . . ? O2 Tb1 C1 95.0(3) 3_666 . ? O6 Tb1 C1 81.4(4) 3_666 . ? O1 Tb1 C1 25.6(4) . . ? N1 Tb1 C1 105.6(3) 3_766 . ? O2 Tb1 C1 25.1(3) . . ? O6 S1 O7 100.5(11) . . ? O6 S1 O5 118.3(10) . . ? O7 S1 O5 114.5(11) . . ? O6 S1 O5 118.1(9) . 3_656 ? O7 S1 O5 112.8(12) . 3_656 ? O5 S1 O5 93.6(10) . 3_656 ? O6 S1 S1 133.5(7) . 3_656 ? O7 S1 S1 125.7(10) . 3_656 ? O5 S1 S1 49.9(8) . 3_656 ? O5 S1 S1 43.7(7) 3_656 3_656 ? C1 O1 Tb1 99.4(9) . . ? C1 O2 Tb1 157.1(8) . 3_666 ? C1 O2 Tb1 92.8(7) . . ? Tb1 O2 Tb1 110.1(4) 3_666 . ? C8 O3 Tb1 152.2(9) . 3_666 ? C8 O4 Tb1 156.2(9) . 4_566 ? S1 O5 S1 86.4(10) . 3_656 ? S1 O5 Tb1 135.6(12) . . ? S1 O5 Tb1 122.0(10) 3_656 . ? S1 O6 Tb1 140.2(8) . 3_666 ? O8 O8 H8A 77.0 3_556 . ? O8 O8 H8B 59.8 3_556 . ? H8A O8 H8B 109.5 . . ? C5 N2 C9 105.6(11) . . ? C5 N2 H2 127.2 . . ? C9 N2 H2 127.2 . . ? C9 N1 C4 106.0(10) . . ? C9 N1 Tb1 116.8(9) . 3_766 ? C4 N1 Tb1 133.6(8) . 3_766 ? O2 C1 O1 117.1(12) . . ? O2 C1 C2 125.3(11) . . ? O1 C1 C2 117.6(11) . . ? O2 C1 Tb1 62.1(7) . . ? O1 C1 Tb1 54.9(7) . . ? C2 C1 Tb1 172.2(8) . . ? C3 C2 C7 118.7(11) . . ? C3 C2 C1 113.7(10) . . ? C7 C2 C1 127.6(11) . . ? C4 C3 C2 120.1(11) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.6(11) . . ? C3 C4 N1 131.2(11) . . ? C5 C4 N1 109.2(11) . . ? N2 C5 C6 131.3(12) . . ? N2 C5 C4 107.1(11) . . ? C6 C5 C4 121.6(12) . . ? C7 C6 C5 119.1(12) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C2 120.8(11) . . ? C6 C7 C8 113.3(11) . . ? C2 C7 C8 125.9(11) . . ? O3 C8 O4 122.5(11) . . ? O3 C8 C7 120.8(11) . . ? O4 C8 C7 116.5(11) . . ? N1 C9 N2 112.1(12) . . ? N1 C9 H9 123.9 . . ? N2 C9 H9 123.9 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 4.254 _refine_diff_density_min -2.024 _refine_diff_density_rms 0.318 # Attachment 'sm.cif' data_Sm _database_code_depnum_ccdc_archive 'CCDC 734656' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 N4 O15 S Sm2' _chemical_formula_sum 'C18 H14 N4 O15 S Sm2' _chemical_formula_weight 859.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4730(11) _cell_length_b 9.8689(11) _cell_length_c 14.2483(16) _cell_angle_alpha 91.4250(10) _cell_angle_beta 107.6770(10) _cell_angle_gamma 118.2570(10) _cell_volume 1095.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2794 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 23.31 _exptl_crystal_description Sheet _exptl_crystal_colour 'Light yellow' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 5.500 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.339 _exptl_absorpt_correction_T_max 0.438 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 area-detector diffractometer' _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 5906 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3992 _reflns_number_gt 3780 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material 'SHELXTL(Bruker, 2002)' _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^)+(0.0381P)^2^+2.1043P] 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 3992 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0740 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _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 0.2873(6) 0.6250(5) -0.2434(3) 0.0128(9) Uani 1 1 d . . . C2 C 0.1641(6) 0.4567(5) -0.2889(3) 0.0136(9) Uani 1 1 d . . . C3 C 0.0422(6) 0.4192(5) -0.3835(4) 0.0165(10) Uani 1 1 d . . . H3 H 0.0263 0.4959 -0.4136 0.020 Uiso 1 1 calc R . . C4 C -0.0556(6) 0.2625(6) -0.4318(3) 0.0169(10) Uani 1 1 d . . . C5 C -0.2241(7) 0.0329(6) -0.5355(4) 0.0267(12) Uani 1 1 d . . . H5 H -0.3045 -0.0427 -0.5933 0.032 Uiso 1 1 calc R . . C6 C -0.0322(6) 0.1461(6) -0.3874(4) 0.0196(10) Uani 1 1 d . . . C7 C 0.0896(6) 0.1830(6) -0.2932(4) 0.0198(10) Uani 1 1 d . . . H7 H 0.1064 0.1057 -0.2645 0.024 Uiso 1 1 calc R . . C8 C 0.1864(6) 0.3380(5) -0.2424(3) 0.0133(9) Uani 1 1 d . . . C9 C 0.3222(6) 0.3753(5) -0.1410(3) 0.0132(9) Uani 1 1 d . . . C10 C 0.0877(6) 0.4639(5) 0.1403(3) 0.0143(9) Uani 1 1 d . . . C11 C 0.1838(6) 0.5007(5) 0.2512(4) 0.0145(9) Uani 1 1 d . . . C12 C 0.1475(6) 0.3764(5) 0.3011(4) 0.0168(10) Uani 1 1 d . . . H12 H 0.0704 0.2731 0.2668 0.020 Uiso 1 1 calc R . . C13 C 0.2312(6) 0.4133(6) 0.4041(4) 0.0168(10) Uani 1 1 d . . . C14 C 0.3441(6) 0.4192(6) 0.5645(4) 0.0170(10) Uani 1 1 d . . . H14 H 0.3699 0.3842 0.6239 0.020 Uiso 1 1 calc R . . C15 C 0.3406(6) 0.5684(6) 0.4578(4) 0.0171(10) Uani 1 1 d . . . C16 C 0.3751(6) 0.6942(6) 0.4083(4) 0.0184(10) Uani 1 1 d . . . H16 H 0.4455 0.7977 0.4434 0.022 Uiso 1 1 calc R . . C17 C 0.2997(6) 0.6580(5) 0.3043(3) 0.0138(9) Uani 1 1 d . . . C18 C 0.3464(6) 0.7910(5) 0.2500(3) 0.0151(9) Uani 1 1 d . . . N1 N -0.1792(6) 0.1856(5) -0.5262(3) 0.0253(10) Uani 1 1 d . . . H1 H -0.2201 0.2274 -0.5709 0.030 Uiso 1 1 calc R . . N2 N -0.1426(6) 0.0021(5) -0.4546(4) 0.0292(11) Uani 1 1 d . . . N3 N 0.4092(6) 0.5672(5) 0.5589(3) 0.0208(9) Uani 1 1 d . . . N4 N 0.2359(5) 0.3230(5) 0.4751(3) 0.0200(9) Uani 1 1 d . . . H4 H 0.1793 0.2221 0.4643 0.024 Uiso 1 1 calc R . . O1 O 0.3155(5) 0.7262(4) -0.2968(2) 0.0203(7) Uani 1 1 d . . . O2 O 0.3767(4) 0.6667(4) -0.1491(2) 0.0181(7) Uani 1 1 d . . . O3 O 0.2927(4) 0.3997(4) -0.0633(2) 0.0180(7) Uani 1 1 d . . . O4 O 0.4518(4) 0.3696(4) -0.1402(3) 0.0216(8) Uani 1 1 d . . . O5 O 0.1488(4) 0.4359(4) 0.0800(3) 0.0196(7) Uani 1 1 d . . . O6 O -0.0527(4) 0.4599(4) 0.1145(3) 0.0230(8) Uani 1 1 d . . . O7 O 0.3149(4) 0.7660(4) 0.1553(2) 0.0184(7) Uani 1 1 d . . . O8 O 0.4155(5) 0.9284(4) 0.2970(3) 0.0261(8) Uani 1 1 d . . . O9 O 0.2779(4) 0.8676(4) -0.0131(3) 0.0187(7) Uani 1 1 d . . . O10 O 0.3574(4) 0.9588(4) -0.1560(3) 0.0208(7) Uani 1 1 d . . . O11 O 0.1154(4) 0.9565(4) -0.1327(3) 0.0214(8) Uani 1 1 d . . . O12 O 0.4025(4) 1.1355(4) -0.0163(3) 0.0192(7) Uani 1 1 d . . . O13 O 0.3392(5) 1.1685(5) 0.2914(3) 0.0306(9) Uani 1 1 d . . . H13B H 0.4278 1.2496 0.3316 0.037 Uiso 1 1 d R . . H13A H 0.2977 1.0938 0.3213 0.037 Uiso 1 1 d R . . O14 O 0.2556(6) 1.2119(5) 0.0938(3) 0.0397(11) Uani 1 1 d . . . H14B H 0.2845 1.2581 0.0475 0.048 Uiso 1 1 d R . . H14A H 0.2786 1.2745 0.1453 0.048 Uiso 1 1 d R . . O15 O 0.0897(5) 0.8986(5) 0.1156(3) 0.0352(10) Uani 1 1 d . . . H15A H 0.0451 0.7995 0.1076 0.042 Uiso 1 1 d R . . H15B H 0.0867 0.9482 0.1639 0.042 Uiso 1 1 d R . . S1 S 0.28330(14) 0.97730(12) -0.08372(8) 0.0124(2) Uani 1 1 d . . . Sm1 Sm 0.32338(3) 0.63780(2) 0.009784(16) 0.01070(8) Uani 1 1 d . . . Sm2 Sm 0.40250(3) 1.06522(3) 0.157469(17) 0.01303(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 0.016(2) 0.014(2) 0.009(2) 0.0034(18) 0.0046(18) 0.0085(19) C2 0.013(2) 0.015(2) 0.013(2) 0.0024(18) 0.0040(19) 0.0065(19) C3 0.018(2) 0.015(2) 0.015(2) 0.0054(19) 0.003(2) 0.010(2) C4 0.018(2) 0.019(2) 0.009(2) 0.0040(19) 0.0008(19) 0.008(2) C5 0.023(3) 0.015(2) 0.016(3) -0.004(2) -0.011(2) 0.001(2) C6 0.020(2) 0.013(2) 0.016(3) 0.0021(19) 0.002(2) 0.003(2) C7 0.022(3) 0.018(2) 0.016(3) 0.006(2) 0.001(2) 0.010(2) C8 0.016(2) 0.015(2) 0.009(2) 0.0033(18) 0.0037(18) 0.0080(19) C9 0.015(2) 0.009(2) 0.011(2) 0.0019(17) 0.0018(19) 0.0051(18) C10 0.014(2) 0.013(2) 0.010(2) 0.0020(17) -0.0013(18) 0.0054(19) C11 0.013(2) 0.019(2) 0.013(2) 0.0073(19) 0.0056(19) 0.0088(19) C12 0.016(2) 0.013(2) 0.020(3) 0.0055(19) 0.005(2) 0.0068(19) C13 0.019(2) 0.017(2) 0.015(2) 0.0057(19) 0.008(2) 0.009(2) C14 0.024(3) 0.023(2) 0.011(2) 0.0110(19) 0.008(2) 0.015(2) C15 0.017(2) 0.020(2) 0.015(2) 0.0036(19) 0.005(2) 0.011(2) C16 0.021(2) 0.015(2) 0.018(3) 0.0042(19) 0.007(2) 0.008(2) C17 0.015(2) 0.014(2) 0.011(2) 0.0051(18) 0.0023(19) 0.0073(19) C18 0.016(2) 0.019(2) 0.009(2) 0.0049(18) 0.0013(18) 0.011(2) N1 0.024(2) 0.019(2) 0.017(2) 0.0044(17) -0.0070(18) 0.0079(19) N2 0.032(3) 0.013(2) 0.024(3) 0.0028(18) -0.003(2) 0.0046(19) N3 0.028(2) 0.024(2) 0.014(2) 0.0067(17) 0.0101(18) 0.014(2) N4 0.025(2) 0.016(2) 0.019(2) 0.0103(17) 0.0088(18) 0.0093(18) O1 0.0287(19) 0.0153(17) 0.0128(17) 0.0076(13) 0.0056(15) 0.0089(15) O2 0.0210(17) 0.0158(16) 0.0120(17) 0.0026(13) 0.0033(14) 0.0067(14) O3 0.0251(18) 0.0191(17) 0.0126(17) 0.0049(13) 0.0055(14) 0.0141(15) O4 0.0181(18) 0.0294(19) 0.0162(18) 0.0043(15) -0.0003(14) 0.0149(16) O5 0.0220(18) 0.0190(17) 0.0174(18) 0.0040(14) 0.0096(15) 0.0085(15) O6 0.0141(17) 0.033(2) 0.0197(19) 0.0054(15) 0.0014(15) 0.0132(16) O7 0.0252(18) 0.0173(17) 0.0131(17) 0.0093(13) 0.0089(14) 0.0097(15) O8 0.039(2) 0.0146(18) 0.0189(19) 0.0062(14) 0.0070(17) 0.0113(16) O9 0.0237(18) 0.0184(17) 0.0163(18) 0.0084(14) 0.0058(15) 0.0129(15) O10 0.0238(19) 0.0284(19) 0.0134(18) 0.0042(14) 0.0076(15) 0.0151(16) O11 0.0136(17) 0.0259(18) 0.0208(19) 0.0024(15) -0.0010(14) 0.0114(15) O12 0.0180(17) 0.0120(16) 0.0193(19) 0.0010(14) 0.0018(15) 0.0044(14) O13 0.036(2) 0.029(2) 0.024(2) -0.0023(16) 0.0108(18) 0.0145(18) O14 0.057(3) 0.050(3) 0.046(3) 0.031(2) 0.033(2) 0.043(2) O15 0.024(2) 0.030(2) 0.050(3) 0.0039(19) 0.0163(19) 0.0112(18) S1 0.0132(5) 0.0115(5) 0.0100(5) 0.0026(4) 0.0015(4) 0.0060(4) Sm1 0.01083(13) 0.01122(13) 0.00848(14) 0.00337(9) 0.00149(10) 0.00550(10) Sm2 0.01465(14) 0.01166(14) 0.01231(14) 0.00436(9) 0.00434(10) 0.00650(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.248(5) . ? C1 O2 1.282(5) . ? C1 C2 1.480(6) . ? C1 Sm2 2.933(5) 2_675 ? C2 C3 1.383(6) . ? C2 C8 1.430(6) . ? C3 C4 1.388(7) . ? C3 H3 0.9300 . ? C4 N1 1.381(6) . ? C4 C6 1.400(7) . ? C5 N2 1.310(7) . ? C5 N1 1.349(7) . ? C5 H5 0.9300 . ? C6 C7 1.379(7) . ? C6 N2 1.395(6) . ? C7 C8 1.385(7) . ? C7 H7 0.9300 . ? C8 C9 1.508(6) . ? C9 O4 1.251(6) . ? C9 O3 1.266(6) . ? C10 O6 1.249(6) . ? C10 O5 1.262(6) . ? C10 C11 1.497(6) . ? C11 C12 1.385(6) . ? C11 C17 1.418(6) . ? C12 C13 1.382(7) . ? C12 H12 0.9300 . ? C13 N4 1.370(6) . ? C13 C15 1.401(7) . ? C14 N3 1.305(6) . ? C14 N4 1.341(6) . ? C14 H14 0.9300 . ? C15 N3 1.392(6) . ? C15 C16 1.395(7) . ? C16 C17 1.386(7) . ? C16 H16 0.9300 . ? C17 C18 1.492(6) . ? C18 O8 1.250(6) . ? C18 O7 1.280(6) . ? C18 Sm2 2.930(5) . ? N1 H1 0.8600 . ? N4 H4 0.8600 . ? O1 Sm2 2.585(3) 2_675 ? O2 Sm1 2.460(3) . ? O2 Sm2 2.513(3) 2_675 ? O3 Sm1 2.395(3) . ? O4 Sm1 2.397(3) 2_665 ? O5 Sm1 2.385(3) . ? O6 Sm1 2.336(3) 2_565 ? O7 Sm1 2.444(3) . ? O7 Sm2 2.659(3) . ? O8 Sm2 2.436(3) . ? O9 S1 1.490(3) . ? O9 Sm1 2.512(3) . ? O9 Sm2 2.636(3) . ? O10 S1 1.462(4) . ? O10 Sm2 2.402(3) 2_675 ? O11 S1 1.438(3) . ? O12 S1 1.494(3) . ? O12 Sm1 2.470(3) 2_675 ? O12 Sm2 2.588(4) . ? O13 Sm2 2.494(4) . ? O13 H13B 0.8500 . ? O13 H13A 0.8500 . ? O14 Sm2 2.462(4) . ? O14 H14B 0.8500 . ? O14 H14A 0.8500 . ? O15 Sm2 2.471(4) . ? O15 H15A 0.8500 . ? O15 H15B 0.8499 . ? S1 Sm2 3.2256(12) . ? Sm1 O6 2.336(3) 2_565 ? Sm1 O4 2.397(3) 2_665 ? Sm1 O12 2.470(3) 2_675 ? Sm2 O10 2.402(3) 2_675 ? Sm2 O2 2.513(3) 2_675 ? Sm2 O1 2.585(3) 2_675 ? Sm2 C1 2.933(5) 2_675 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 119.0(4) . . ? O1 C1 C2 120.8(4) . . ? O2 C1 C2 119.9(4) . . ? O1 C1 Sm2 61.6(2) . 2_675 ? O2 C1 Sm2 58.5(2) . 2_675 ? C2 C1 Sm2 164.7(3) . 2_675 ? C3 C2 C8 121.1(4) . . ? C3 C2 C1 117.9(4) . . ? C8 C2 C1 120.4(4) . . ? C2 C3 C4 117.4(4) . . ? C2 C3 H3 121.3 . . ? C4 C3 H3 121.3 . . ? N1 C4 C3 132.9(4) . . ? N1 C4 C6 105.2(4) . . ? C3 C4 C6 121.8(4) . . ? N2 C5 N1 113.0(4) . . ? N2 C5 H5 123.5 . . ? N1 C5 H5 123.5 . . ? C7 C6 N2 129.9(5) . . ? C7 C6 C4 121.0(4) . . ? N2 C6 C4 109.0(4) . . ? C6 C7 C8 118.4(4) . . ? C6 C7 H7 120.8 . . ? C8 C7 H7 120.8 . . ? C7 C8 C2 120.2(4) . . ? C7 C8 C9 117.1(4) . . ? C2 C8 C9 122.5(4) . . ? O4 C9 O3 124.7(4) . . ? O4 C9 C8 116.9(4) . . ? O3 C9 C8 118.2(4) . . ? O6 C10 O5 124.5(4) . . ? O6 C10 C11 115.9(4) . . ? O5 C10 C11 119.6(4) . . ? C12 C11 C17 121.1(4) . . ? C12 C11 C10 117.6(4) . . ? C17 C11 C10 121.1(4) . . ? C13 C12 C11 116.8(4) . . ? C13 C12 H12 121.6 . . ? C11 C12 H12 121.6 . . ? N4 C13 C12 132.7(4) . . ? N4 C13 C15 104.7(4) . . ? C12 C13 C15 122.5(4) . . ? N3 C14 N4 112.6(4) . . ? N3 C14 H14 123.7 . . ? N4 C14 H14 123.7 . . ? N3 C15 C16 130.0(5) . . ? N3 C15 C13 109.0(4) . . ? C16 C15 C13 120.9(4) . . ? C17 C16 C15 117.0(4) . . ? C17 C16 H16 121.5 . . ? C15 C16 H16 121.5 . . ? C16 C17 C11 121.5(4) . . ? C16 C17 C18 117.4(4) . . ? C11 C17 C18 121.1(4) . . ? O8 C18 O7 119.5(4) . . ? O8 C18 C17 119.8(4) . . ? O7 C18 C17 120.7(4) . . ? O8 C18 Sm2 54.9(2) . . ? O7 C18 Sm2 65.1(2) . . ? C17 C18 Sm2 170.2(3) . . ? C5 N1 C4 107.4(4) . . ? C5 N1 H1 126.3 . . ? C4 N1 H1 126.3 . . ? C5 N2 C6 105.4(4) . . ? C14 N3 C15 105.4(4) . . ? C14 N4 C13 108.2(4) . . ? C14 N4 H4 125.9 . . ? C13 N4 H4 125.9 . . ? C1 O1 Sm2 93.2(3) . 2_675 ? C1 O2 Sm1 137.3(3) . . ? C1 O2 Sm2 95.8(3) . 2_675 ? Sm1 O2 Sm2 116.64(13) . 2_675 ? C9 O3 Sm1 127.3(3) . . ? C9 O4 Sm1 132.9(3) . 2_665 ? C10 O5 Sm1 121.7(3) . . ? C10 O6 Sm1 146.5(3) . 2_565 ? C18 O7 Sm1 149.9(3) . . ? C18 O7 Sm2 89.0(3) . . ? Sm1 O7 Sm2 114.28(12) . . ? C18 O8 Sm2 100.3(3) . . ? S1 O9 Sm1 140.0(2) . . ? S1 O9 Sm2 99.05(16) . . ? Sm1 O9 Sm2 112.79(12) . . ? S1 O10 Sm2 138.9(2) . 2_675 ? S1 O12 Sm1 133.8(2) . 2_675 ? S1 O12 Sm2 101.00(16) . . ? Sm1 O12 Sm2 113.60(12) 2_675 . ? Sm2 O13 H13B 112.0 . . ? Sm2 O13 H13A 106.6 . . ? H13B O13 H13A 112.1 . . ? Sm2 O14 H14B 113.1 . . ? Sm2 O14 H14A 105.0 . . ? H14B O14 H14A 113.2 . . ? Sm2 O15 H15A 119.4 . . ? Sm2 O15 H15B 95.0 . . ? H15A O15 H15B 119.4 . . ? O11 S1 O10 111.9(2) . . ? O11 S1 O9 110.7(2) . . ? O10 S1 O9 110.8(2) . . ? O11 S1 O12 110.9(2) . . ? O10 S1 O12 109.0(2) . . ? O9 S1 O12 103.2(2) . . ? O11 S1 Sm2 111.21(16) . . ? O10 S1 Sm2 136.80(14) . . ? O9 S1 Sm2 53.81(14) . . ? O12 S1 Sm2 51.96(14) . . ? O6 Sm1 O5 79.22(12) 2_565 . ? O6 Sm1 O3 82.04(12) 2_565 . ? O5 Sm1 O3 73.95(12) . . ? O6 Sm1 O4 157.28(13) 2_565 2_665 ? O5 Sm1 O4 81.83(12) . 2_665 ? O3 Sm1 O4 80.76(11) . 2_665 ? O6 Sm1 O7 105.34(12) 2_565 . ? O5 Sm1 O7 72.64(11) . . ? O3 Sm1 O7 143.59(11) . . ? O4 Sm1 O7 80.57(12) 2_665 . ? O6 Sm1 O2 75.05(12) 2_565 . ? O5 Sm1 O2 138.26(11) . . ? O3 Sm1 O2 70.41(11) . . ? O4 Sm1 O2 112.51(12) 2_665 . ? O7 Sm1 O2 145.97(11) . . ? O6 Sm1 O12 127.46(12) 2_565 2_675 ? O5 Sm1 O12 153.06(12) . 2_675 ? O3 Sm1 O12 109.98(12) . 2_675 ? O4 Sm1 O12 72.85(12) 2_665 2_675 ? O7 Sm1 O12 93.86(11) . 2_675 ? O2 Sm1 O12 63.08(11) . 2_675 ? O6 Sm1 O9 73.57(12) 2_565 . ? O5 Sm1 O9 118.59(11) . . ? O3 Sm1 O9 148.96(11) . . ? O4 Sm1 O9 127.23(12) 2_665 . ? O7 Sm1 O9 63.63(11) . . ? O2 Sm1 O9 84.73(11) . . ? O12 Sm1 O9 72.40(11) 2_675 . ? O10 Sm2 O8 83.48(13) 2_675 . ? O10 Sm2 O14 140.92(13) 2_675 . ? O8 Sm2 O14 133.56(14) . . ? O10 Sm2 O15 139.48(13) 2_675 . ? O8 Sm2 O15 82.89(14) . . ? O14 Sm2 O15 69.34(15) . . ? O10 Sm2 O13 133.46(12) 2_675 . ? O8 Sm2 O13 68.71(13) . . ? O14 Sm2 O13 68.45(14) . . ? O15 Sm2 O13 74.68(14) . . ? O10 Sm2 O2 74.48(12) 2_675 2_675 ? O8 Sm2 O2 127.92(12) . 2_675 ? O14 Sm2 O2 71.84(13) . 2_675 ? O15 Sm2 O2 141.09(13) . 2_675 ? O13 Sm2 O2 93.65(12) . 2_675 ? O10 Sm2 O12 82.26(11) 2_675 . ? O8 Sm2 O12 160.02(11) . . ? O14 Sm2 O12 64.26(13) . . ? O15 Sm2 O12 99.10(13) . . ? O13 Sm2 O12 131.11(12) . . ? O2 Sm2 O12 60.71(10) 2_675 . ? O10 Sm2 O1 68.37(12) 2_675 2_675 ? O8 Sm2 O1 77.51(11) . 2_675 ? O14 Sm2 O1 103.30(14) . 2_675 ? O15 Sm2 O1 143.51(13) . 2_675 ? O13 Sm2 O1 69.61(12) . 2_675 ? O2 Sm2 O1 50.60(10) 2_675 2_675 ? O12 Sm2 O1 109.77(10) . 2_675 ? O10 Sm2 O9 76.75(11) 2_675 . ? O8 Sm2 O9 109.73(11) . . ? O14 Sm2 O9 96.72(13) . . ? O15 Sm2 O9 72.39(13) . . ? O13 Sm2 O9 146.93(12) . . ? O2 Sm2 O9 110.08(11) 2_675 . ? O12 Sm2 O9 53.18(10) . . ? O1 Sm2 O9 143.43(11) 2_675 . ? O10 Sm2 O7 72.57(11) 2_675 . ? O8 Sm2 O7 50.58(11) . . ? O14 Sm2 O7 136.86(14) . . ? O15 Sm2 O7 69.30(12) . . ? O13 Sm2 O7 111.16(12) . . ? O2 Sm2 O7 146.92(11) 2_675 . ? O12 Sm2 O7 111.35(10) . . ? O1 Sm2 O7 117.18(10) 2_675 . ? O9 Sm2 O7 59.15(10) . . ? O10 Sm2 C1 72.19(12) 2_675 2_675 ? O8 Sm2 C1 102.63(12) . 2_675 ? O14 Sm2 C1 85.41(14) . 2_675 ? O15 Sm2 C1 148.21(13) . 2_675 ? O13 Sm2 C1 78.29(13) . 2_675 ? O2 Sm2 C1 25.77(11) 2_675 2_675 ? O12 Sm2 C1 86.21(11) . 2_675 ? O1 Sm2 C1 25.13(11) 2_675 2_675 ? O9 Sm2 C1 131.60(12) . 2_675 ? O7 Sm2 C1 137.68(11) . 2_675 ? O10 Sm2 C18 78.92(12) 2_675 . ? O8 Sm2 C18 24.83(12) . . ? O14 Sm2 C18 139.58(14) . . ? O15 Sm2 C18 72.87(14) . . ? O13 Sm2 C18 88.38(13) . . ? O2 Sm2 C18 145.03(12) 2_675 . ? O12 Sm2 C18 137.11(12) . . ? O1 Sm2 C18 98.46(11) 2_675 . ? O9 Sm2 C18 84.96(12) . . ? O7 Sm2 C18 25.91(12) . . ? C1 Sm2 C18 123.02(12) 2_675 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.86 2.00 2.825(5) 161.7 2_564 N4 H4 N2 0.86 2.06 2.876(6) 157.1 2 O13 H13B N3 0.85 1.96 2.789(6) 165.2 2_676 O13 H13A N2 0.85 2.67 3.401(6) 144.9 2_565 O14 H14B O3 0.85 2.13 2.938(5) 158.8 1_565 O15 H15B O11 0.85 2.44 2.963(5) 120.4 2_575 O15 H15A O7 0.85 2.62 2.921(5) 102.3 . O15 H15B O13 0.85 2.45 3.011(6) 124.5 . _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.840 _refine_diff_density_min -1.611 _refine_diff_density_rms 0.169