# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Xu, Jing' _publ_contact_author_email xujing@fjirsm.ac.cn loop_ _publ_author_name 'Jing Xu' 'Weiping Su' 'Maochun Hong' data_1_776571 _database_code_depnum_ccdc_archive 'CCDC 776571' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cu0.50 Eu2 N3 O17 S' _chemical_formula_weight 938.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.503(6) _cell_length_b 10.907(7) _cell_length_c 13.045(7) _cell_angle_alpha 88.62(2) _cell_angle_beta 66.884(15) _cell_angle_gamma 80.085(17) _cell_volume 1352.3(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3741 _cell_measurement_theta_min 2.1420 _cell_measurement_theta_max 27.4487 _exptl_crystal_description Prism _exptl_crystal_colour Light-blue _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0800 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 899 _exptl_absorpt_coefficient_mu 5.143 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.604 _exptl_absorpt_correction_T_max 0.663 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'SCXmini CCD' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10640 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0868 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.45 _reflns_number_total 5934 _reflns_number_gt 4939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0688P)^2^+5.5775P] 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 SHELXL _refine_ls_extinction_coef 0.0071(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5934 _refine_ls_number_parameters 395 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1686 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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 0.98382(5) 0.61394(4) 0.13151(4) 0.02244(18) Uani 1 1 d . . . Eu2 Eu 0.60126(5) 0.40141(4) 0.18883(4) 0.02422(19) Uani 1 1 d . . . Cu Cu 0.5000 0.0000 0.5000 0.0407(5) Uani 1 2 d S . . S S 0.7524(2) 0.6594(2) 0.0314(2) 0.0252(5) Uani 1 1 d . . . O1 O 0.8603(7) 0.7218(6) 0.3104(6) 0.0313(15) Uani 1 1 d . . . O2 O 0.7583(9) 0.8988(8) 0.4175(7) 0.055(2) Uani 1 1 d . . . O3 O 1.1602(6) 0.6875(6) -0.0352(5) 0.0269(14) Uani 1 1 d . . . O4 O 1.2839(8) 0.8298(7) -0.1277(6) 0.0430(19) Uani 1 1 d . . . O5 O 1.2039(7) 0.5986(7) 0.1607(6) 0.0311(16) Uani 1 1 d . . . O6 O 1.3653(7) 0.4982(7) 0.2193(6) 0.0386(18) Uani 1 1 d . . . O7 O 0.7979(7) 0.4847(6) 0.2204(5) 0.0274(14) Uani 1 1 d . . . O8 O 0.7231(7) 0.3235(7) 0.3156(6) 0.0407(19) Uani 1 1 d . . . O9 O 0.8933(7) 0.5713(6) -0.0174(5) 0.0275(14) Uani 1 1 d . . . O10 O 0.7688(7) 0.7372(7) 0.1160(6) 0.0332(16) Uani 1 1 d . . . O11 O 0.6423(7) 0.5820(6) 0.0845(6) 0.0312(16) Uani 1 1 d . . . O12 O 0.7221(8) 0.7287(7) -0.0540(6) 0.0348(17) Uani 1 1 d . . . O13 O 0.4907(8) 0.5300(8) 0.3637(6) 0.0401(18) Uani 1 1 d . . . H13A H 0.4865 0.5368 0.3000 0.048 Uiso 1 1 d R . . H13B H 0.4179 0.5756 0.4105 0.048 Uiso 1 1 d R . . O14 O 0.5655(7) 0.3460(7) 0.0219(6) 0.0372(18) Uani 1 1 d . . . H14A H 0.6422 0.3114 -0.0293 0.045 Uiso 1 1 d R . . H14B H 0.4990 0.3383 0.0022 0.045 Uiso 1 1 d R . . O15 O 0.4610(7) 0.2587(7) 0.2928(6) 0.0356(16) Uani 1 1 d . . . O16 O 0.5176(8) 0.1544(7) 0.4233(6) 0.0393(18) Uani 1 1 d . . . O17 O 0.6384(9) 0.6212(7) 0.4611(6) 0.0433(19) Uani 1 1 d . . . H17B H 0.6014 0.6946 0.4893 0.052 Uiso 1 1 d R . . H17C H 0.7137 0.6257 0.4048 0.052 Uiso 1 1 d R . . N1 N 1.0152(8) 0.8371(7) 0.1425(6) 0.0260(17) Uani 1 1 d . . . N2 N 1.0205(8) 0.4582(8) 0.2729(7) 0.0287(18) Uani 1 1 d . . . N3 N 0.4560(10) -0.0512(9) 0.3725(8) 0.039(2) Uani 1 1 d . . . C1 C 0.9358(11) 0.9087(11) 0.2372(8) 0.035(2) Uani 1 1 d . . . C2 C 0.9448(13) 1.0324(10) 0.2440(9) 0.041(3) Uani 1 1 d . . . H2A H 0.8849 1.0817 0.3073 0.050 Uiso 1 1 calc R . . C3 C 1.0417(14) 1.0827(12) 0.1579(10) 0.049(3) Uani 1 1 d . . . H3A H 1.0526 1.1646 0.1649 0.058 Uiso 1 1 calc R . . C4 C 1.1259(12) 1.0102(10) 0.0579(9) 0.037(2) Uani 1 1 d . . . H4A H 1.1903 1.0433 -0.0028 0.045 Uiso 1 1 calc R . . C5 C 1.1076(9) 0.8875(9) 0.0550(8) 0.025(2) Uani 1 1 d . . . C6 C 0.8402(11) 0.8395(10) 0.3309(8) 0.033(2) Uani 1 1 d . . . C7 C 1.1898(11) 0.7985(10) -0.0438(8) 0.032(2) Uani 1 1 d . . . C8 C 1.1349(10) 0.4502(10) 0.2982(8) 0.030(2) Uani 1 1 d . . . C9 C 1.1464(11) 0.3813(12) 0.3851(9) 0.039(3) Uani 1 1 d . . . H9A H 1.2257 0.3777 0.4011 0.047 Uiso 1 1 calc R . . C10 C 1.0403(12) 0.3173(13) 0.4492(10) 0.046(3) Uani 1 1 d . . . H10A H 1.0440 0.2753 0.5111 0.055 Uiso 1 1 calc R . . C11 C 0.9278(12) 0.3185(12) 0.4168(10) 0.045(3) Uani 1 1 d . . . H11A H 0.8595 0.2703 0.4527 0.054 Uiso 1 1 calc R . . C12 C 0.9190(10) 0.3926(10) 0.3305(7) 0.026(2) Uani 1 1 d . . . C13 C 1.2448(10) 0.5205(9) 0.2207(7) 0.027(2) Uani 1 1 d . . . C14 C 0.8066(11) 0.3977(10) 0.2888(8) 0.028(2) Uani 1 1 d . . . C15 C 0.4509(12) 0.0417(11) 0.3043(10) 0.039(3) Uani 1 1 d . . . C16 C 0.4183(16) 0.0312(14) 0.2127(11) 0.061(4) Uani 1 1 d . . . H16A H 0.4122 0.0989 0.1692 0.074 Uiso 1 1 calc R . . C17 C 0.3944(16) -0.0858(13) 0.1870(13) 0.062(4) Uani 1 1 d . . . H17A H 0.3761 -0.0975 0.1241 0.075 Uiso 1 1 calc R . . C18 C 0.3986(15) -0.1829(13) 0.2570(13) 0.061(4) Uani 1 1 d . . . H18A H 0.3823 -0.2602 0.2418 0.073 Uiso 1 1 calc R . . C19 C 0.4277(15) -0.1632(12) 0.3512(12) 0.057(4) Uani 1 1 d . . . H19A H 0.4277 -0.2273 0.3996 0.069 Uiso 1 1 calc R . . C20 C 0.4791(11) 0.1612(10) 0.3399(8) 0.032(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.0204(3) 0.0240(3) 0.0244(3) 0.00294(19) -0.0097(2) -0.0062(2) Eu2 0.0206(3) 0.0275(3) 0.0263(3) 0.0047(2) -0.0104(2) -0.0066(2) Cu 0.0441(11) 0.0457(12) 0.0352(10) 0.0035(9) -0.0149(9) -0.0176(10) S 0.0216(11) 0.0254(12) 0.0322(13) 0.0055(10) -0.0136(10) -0.0066(9) O1 0.037(4) 0.026(4) 0.028(4) 0.000(3) -0.010(3) -0.007(3) O2 0.054(5) 0.049(5) 0.040(5) -0.010(4) 0.004(4) -0.004(4) O3 0.022(3) 0.028(4) 0.028(3) 0.000(3) -0.006(3) -0.008(3) O4 0.041(4) 0.039(5) 0.042(5) 0.008(4) -0.005(4) -0.018(4) O5 0.020(3) 0.043(4) 0.034(4) 0.007(3) -0.013(3) -0.008(3) O6 0.024(4) 0.048(5) 0.054(5) 0.015(4) -0.022(4) -0.018(3) O7 0.020(3) 0.034(4) 0.033(4) 0.005(3) -0.015(3) -0.006(3) O8 0.033(4) 0.050(5) 0.049(5) 0.021(4) -0.020(4) -0.024(4) O9 0.025(3) 0.027(4) 0.031(4) -0.004(3) -0.011(3) -0.005(3) O10 0.030(4) 0.033(4) 0.041(4) -0.005(3) -0.018(3) -0.005(3) O11 0.019(3) 0.029(4) 0.045(4) 0.006(3) -0.012(3) -0.005(3) O12 0.041(4) 0.037(4) 0.030(4) 0.012(3) -0.019(3) -0.004(3) O13 0.029(4) 0.055(5) 0.031(4) -0.008(4) -0.007(3) -0.006(4) O14 0.026(4) 0.055(5) 0.033(4) 0.000(3) -0.014(3) -0.007(3) O15 0.030(4) 0.033(4) 0.037(4) 0.003(3) -0.006(3) -0.005(3) O16 0.040(4) 0.035(4) 0.044(5) -0.005(3) -0.017(4) -0.007(4) O17 0.052(5) 0.036(4) 0.038(4) -0.003(3) -0.009(4) -0.015(4) N1 0.023(4) 0.025(4) 0.028(4) 0.000(3) -0.007(3) -0.006(3) N2 0.024(4) 0.036(5) 0.031(4) 0.000(4) -0.015(4) -0.010(4) N3 0.037(5) 0.034(5) 0.049(6) 0.000(4) -0.018(4) -0.011(4) C1 0.032(5) 0.042(6) 0.026(5) -0.002(4) -0.004(4) -0.012(5) C2 0.050(7) 0.029(6) 0.034(6) -0.006(5) -0.004(5) -0.007(5) C3 0.061(8) 0.037(7) 0.050(7) -0.005(5) -0.021(6) -0.014(6) C4 0.036(6) 0.036(6) 0.040(6) 0.009(5) -0.013(5) -0.011(5) C5 0.022(4) 0.030(5) 0.023(5) 0.008(4) -0.009(4) -0.005(4) C6 0.035(6) 0.035(6) 0.026(5) 0.002(4) -0.009(5) -0.007(5) C7 0.035(6) 0.032(6) 0.035(6) 0.013(4) -0.017(5) -0.012(5) C8 0.022(5) 0.042(6) 0.029(5) -0.004(4) -0.015(4) -0.004(4) C9 0.024(5) 0.063(8) 0.035(6) 0.009(5) -0.018(5) -0.008(5) C10 0.033(6) 0.069(9) 0.042(7) 0.029(6) -0.020(5) -0.018(6) C11 0.037(6) 0.060(8) 0.052(7) 0.023(6) -0.025(6) -0.029(6) C12 0.024(5) 0.036(6) 0.014(4) -0.003(4) -0.002(4) -0.005(4) C13 0.031(5) 0.036(6) 0.015(4) -0.002(4) -0.009(4) -0.013(4) C14 0.033(5) 0.035(6) 0.025(5) 0.007(4) -0.017(4) -0.013(4) C15 0.038(6) 0.037(6) 0.044(6) 0.016(5) -0.019(5) -0.008(5) C16 0.084(11) 0.060(9) 0.051(8) 0.006(7) -0.037(8) -0.017(8) C17 0.081(10) 0.047(8) 0.075(10) 0.001(7) -0.052(9) -0.004(7) C18 0.064(9) 0.040(8) 0.089(11) -0.010(7) -0.040(8) -0.007(7) C19 0.064(9) 0.038(7) 0.082(10) -0.008(7) -0.039(8) -0.015(6) C20 0.028(5) 0.039(6) 0.023(5) 0.008(4) -0.002(4) -0.008(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 O9 2.388(7) 2_765 ? Eu1 O1 2.397(7) . ? Eu1 O3 2.464(6) . ? Eu1 O5 2.464(6) . ? Eu1 O7 2.497(6) . ? Eu1 O10 2.500(7) . ? Eu1 N1 2.527(8) . ? Eu1 O9 2.557(6) . ? Eu1 N2 2.573(8) . ? Eu1 S 3.147(3) . ? Eu1 Eu1 4.155(2) 2_765 ? Eu2 O15 2.357(7) . ? Eu2 O11 2.371(7) . ? Eu2 O6 2.400(7) 1_455 ? Eu2 O14 2.456(7) . ? Eu2 O13 2.456(8) . ? Eu2 O8 2.513(7) . ? Eu2 O3 2.559(6) 2_765 ? Eu2 O7 2.568(6) . ? Eu2 O4 2.597(8) 2_765 ? Eu2 C7 2.906(11) 2_765 ? Eu2 C14 2.921(9) . ? Eu2 H13A 1.9633 . ? Cu O16 1.937(8) . ? Cu O16 1.937(8) 2_656 ? Cu N3 2.006(9) . ? Cu N3 2.006(9) 2_656 ? S O12 1.438(7) . ? S O11 1.486(6) . ? S O10 1.487(7) . ? S O9 1.522(7) . ? O1 C6 1.282(12) . ? O2 C6 1.231(13) . ? O3 C7 1.293(11) . ? O3 Eu2 2.559(6) 2_765 ? O4 C7 1.241(12) . ? O4 Eu2 2.597(8) 2_765 ? O5 C13 1.276(11) . ? O6 C13 1.240(11) . ? O6 Eu2 2.400(7) 1_655 ? O7 C14 1.303(11) . ? O8 C14 1.240(11) . ? O9 Eu1 2.388(7) 2_765 ? O13 H13A 0.8500 . ? O13 H13B 0.8500 . ? O14 H14A 0.8500 . ? O14 H14B 0.8500 . ? O15 C20 1.238(12) . ? O16 C20 1.299(12) . ? O17 H17B 0.8501 . ? O17 H17C 0.8500 . ? N1 C5 1.352(11) . ? N1 C1 1.358(13) . ? N2 C12 1.349(12) . ? N2 C8 1.355(11) . ? N3 C15 1.341(14) . ? N3 C19 1.365(14) . ? C1 C2 1.376(15) . ? C1 C6 1.525(14) . ? C2 C3 1.365(16) . ? C2 H2A 0.9300 . ? C3 C4 1.419(16) . ? C3 H3A 0.9300 . ? C4 C5 1.387(14) . ? C4 H4A 0.9300 . ? C5 C7 1.498(15) . ? C7 Eu2 2.906(11) 2_765 ? C8 C9 1.378(14) . ? C8 C13 1.514(13) . ? C9 C10 1.391(15) . ? C9 H9A 0.9300 . ? C10 C11 1.400(14) . ? C10 H10A 0.9300 . ? C11 C12 1.394(14) . ? C11 H11A 0.9300 . ? C12 C14 1.473(13) . ? C15 C16 1.377(17) . ? C15 C20 1.507(16) . ? C16 C17 1.415(19) . ? C16 H16A 0.9300 . ? C17 C18 1.388(19) . ? C17 H17A 0.9300 . ? C18 C19 1.408(19) . ? C18 H18A 0.9300 . ? C19 H19A 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 O9 Eu1 O1 151.5(2) 2_765 . ? O9 Eu1 O3 75.9(2) 2_765 . ? O1 Eu1 O3 126.9(2) . . ? O9 Eu1 O5 82.7(2) 2_765 . ? O1 Eu1 O5 88.8(2) . . ? O3 Eu1 O5 71.7(2) . . ? O9 Eu1 O7 83.4(2) 2_765 . ? O1 Eu1 O7 79.7(2) . . ? O3 Eu1 O7 151.1(2) . . ? O5 Eu1 O7 125.8(2) . . ? O9 Eu1 O10 120.9(2) 2_765 . ? O1 Eu1 O10 76.6(2) . . ? O3 Eu1 O10 97.9(2) . . ? O5 Eu1 O10 151.8(2) . . ? O7 Eu1 O10 75.7(2) . . ? O9 Eu1 N1 138.1(2) 2_765 . ? O1 Eu1 N1 63.9(2) . . ? O3 Eu1 N1 63.5(2) . . ? O5 Eu1 N1 75.4(2) . . ? O7 Eu1 N1 138.2(2) . . ? O10 Eu1 N1 76.5(2) . . ? O9 Eu1 O9 65.7(3) 2_765 . ? O1 Eu1 O9 129.5(2) . . ? O3 Eu1 O9 79.1(2) . . ? O5 Eu1 O9 141.3(2) . . ? O7 Eu1 O9 74.0(2) . . ? O10 Eu1 O9 55.6(2) . . ? N1 Eu1 O9 113.4(2) . . ? O9 Eu1 N2 77.3(3) 2_765 . ? O1 Eu1 N2 74.6(3) . . ? O3 Eu1 N2 129.3(2) . . ? O5 Eu1 N2 62.8(2) . . ? O7 Eu1 N2 63.0(2) . . ? O10 Eu1 N2 132.9(2) . . ? N1 Eu1 N2 120.7(3) . . ? O9 Eu1 N2 125.6(2) . . ? O9 Eu1 S 93.32(16) 2_765 . ? O1 Eu1 S 101.37(18) . . ? O3 Eu1 S 92.73(16) . . ? O5 Eu1 S 164.42(16) . . ? O7 Eu1 S 68.29(15) . . ? O10 Eu1 S 27.62(16) . . ? N1 Eu1 S 98.32(18) . . ? O9 Eu1 S 28.65(16) . . ? N2 Eu1 S 131.12(17) . . ? O9 Eu1 Eu1 34.11(15) 2_765 2_765 ? O1 Eu1 Eu1 153.69(16) . 2_765 ? O3 Eu1 Eu1 75.13(15) . 2_765 ? O5 Eu1 Eu1 114.07(17) . 2_765 ? O7 Eu1 Eu1 76.37(16) . 2_765 ? O10 Eu1 Eu1 86.99(16) . 2_765 ? N1 Eu1 Eu1 132.26(18) . 2_765 ? O9 Eu1 Eu1 31.58(15) . 2_765 ? N2 Eu1 Eu1 103.42(19) . 2_765 ? S Eu1 Eu1 59.55(5) . 2_765 ? O15 Eu2 O11 154.2(2) . . ? O15 Eu2 O6 75.5(2) . 1_455 ? O11 Eu2 O6 79.0(2) . 1_455 ? O15 Eu2 O14 90.8(2) . . ? O11 Eu2 O14 78.2(2) . . ? O6 Eu2 O14 74.1(3) 1_455 . ? O15 Eu2 O13 84.0(3) . . ? O11 Eu2 O13 90.6(3) . . ? O6 Eu2 O13 68.9(3) 1_455 . ? O14 Eu2 O13 142.7(3) . . ? O15 Eu2 O8 78.4(2) . . ? O11 Eu2 O8 123.6(2) . . ? O6 Eu2 O8 134.0(3) 1_455 . ? O14 Eu2 O8 143.5(3) . . ? O13 Eu2 O8 71.3(3) . . ? O15 Eu2 O3 117.5(2) . 2_765 ? O11 Eu2 O3 81.1(2) . 2_765 ? O6 Eu2 O3 142.6(2) 1_455 2_765 ? O14 Eu2 O3 71.0(2) . 2_765 ? O13 Eu2 O3 142.8(2) . 2_765 ? O8 Eu2 O3 83.2(2) . 2_765 ? O15 Eu2 O7 129.0(2) . . ? O11 Eu2 O7 72.4(2) . . ? O6 Eu2 O7 131.3(2) 1_455 . ? O14 Eu2 O7 133.9(2) . . ? O13 Eu2 O7 72.9(2) . . ? O8 Eu2 O7 51.4(2) . . ? O3 Eu2 O7 70.1(2) 2_765 . ? O15 Eu2 O4 66.6(2) . 2_765 ? O11 Eu2 O4 129.0(2) . 2_765 ? O6 Eu2 O4 127.0(2) 1_455 2_765 ? O14 Eu2 O4 71.0(3) . 2_765 ? O13 Eu2 O4 137.2(3) . 2_765 ? O8 Eu2 O4 72.8(3) . 2_765 ? O3 Eu2 O4 51.0(2) 2_765 2_765 ? O7 Eu2 O4 101.5(2) . 2_765 ? O15 Eu2 C7 91.5(3) . 2_765 ? O11 Eu2 C7 104.3(3) . 2_765 ? O6 Eu2 C7 136.4(3) 1_455 2_765 ? O14 Eu2 C7 64.5(3) . 2_765 ? O13 Eu2 C7 152.2(3) . 2_765 ? O8 Eu2 C7 80.9(3) . 2_765 ? O3 Eu2 C7 26.4(2) 2_765 2_765 ? O7 Eu2 C7 89.3(2) . 2_765 ? O4 Eu2 C7 25.3(2) 2_765 2_765 ? O15 Eu2 C14 103.2(3) . . ? O11 Eu2 C14 98.8(2) . . ? O6 Eu2 C14 139.9(3) 1_455 . ? O14 Eu2 C14 145.4(3) . . ? O13 Eu2 C14 71.1(3) . . ? O8 Eu2 C14 25.0(2) . . ? O3 Eu2 C14 74.4(3) 2_765 . ? O7 Eu2 C14 26.5(2) . . ? O4 Eu2 C14 85.6(3) 2_765 . ? C7 Eu2 C14 83.4(3) 2_765 . ? O15 Eu2 H13A 91.2 . . ? O11 Eu2 H13A 77.3 . . ? O6 Eu2 H13A 54.7 1_455 . ? O14 Eu2 H13A 126.2 . . ? O13 Eu2 H13A 18.1 . . ? O8 Eu2 H13A 89.1 . . ? O3 Eu2 H13A 147.8 2_765 . ? O7 Eu2 H13A 80.7 . . ? O4 Eu2 H13A 153.3 2_765 . ? C7 Eu2 H13A 168.9 2_765 . ? C14 Eu2 H13A 85.5 . . ? O16 Cu O16 180.0(5) . 2_656 ? O16 Cu N3 82.7(3) . . ? O16 Cu N3 97.3(3) 2_656 . ? O16 Cu N3 97.3(3) . 2_656 ? O16 Cu N3 82.7(3) 2_656 2_656 ? N3 Cu N3 180.000(1) . 2_656 ? O12 S O11 108.8(4) . . ? O12 S O10 114.4(4) . . ? O11 S O10 111.4(4) . . ? O12 S O9 111.3(4) . . ? O11 S O9 107.4(4) . . ? O10 S O9 103.2(4) . . ? O12 S Eu1 139.6(3) . . ? O11 S Eu1 111.4(3) . . ? O10 S Eu1 51.2(3) . . ? O9 S Eu1 53.6(2) . . ? C6 O1 Eu1 126.5(6) . . ? C7 O3 Eu1 124.6(6) . . ? C7 O3 Eu2 91.9(6) . 2_765 ? Eu1 O3 Eu2 137.8(3) . 2_765 ? C7 O4 Eu2 91.4(7) . 2_765 ? C13 O5 Eu1 125.9(6) . . ? C13 O6 Eu2 163.6(7) . 1_655 ? C14 O7 Eu1 123.4(5) . . ? C14 O7 Eu2 92.1(5) . . ? Eu1 O7 Eu2 141.3(3) . . ? C14 O8 Eu2 96.2(6) . . ? S O9 Eu1 144.2(4) . 2_765 ? S O9 Eu1 97.7(3) . . ? Eu1 O9 Eu1 114.3(3) 2_765 . ? S O10 Eu1 101.2(4) . . ? S O11 Eu2 141.6(4) . . ? Eu2 O13 H13A 46.0 . . ? Eu2 O13 H13B 148.5 . . ? H13A O13 H13B 107.7 . . ? Eu2 O14 H14A 111.3 . . ? Eu2 O14 H14B 139.8 . . ? H14A O14 H14B 107.7 . . ? C20 O15 Eu2 136.4(7) . . ? C20 O16 Cu 114.9(7) . . ? H17B O17 H17C 107.7 . . ? C5 N1 C1 119.3(9) . . ? C5 N1 Eu1 121.3(6) . . ? C1 N1 Eu1 119.4(6) . . ? C12 N2 C8 119.3(8) . . ? C12 N2 Eu1 120.0(6) . . ? C8 N2 Eu1 120.4(6) . . ? C15 N3 C19 118.9(11) . . ? C15 N3 Cu 112.5(7) . . ? C19 N3 Cu 128.5(9) . . ? N1 C1 C2 120.9(9) . . ? N1 C1 C6 114.1(9) . . ? C2 C1 C6 124.9(10) . . ? C3 C2 C1 120.1(10) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 120.0(11) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 116.8(10) . . ? C5 C4 H4A 121.6 . . ? C3 C4 H4A 121.6 . . ? N1 C5 C4 122.7(9) . . ? N1 C5 C7 114.1(8) . . ? C4 C5 C7 123.3(9) . . ? O2 C6 O1 127.3(10) . . ? O2 C6 C1 118.5(10) . . ? O1 C6 C1 114.1(9) . . ? O4 C7 O3 122.3(10) . . ? O4 C7 C5 121.2(9) . . ? O3 C7 C5 116.5(8) . . ? O4 C7 Eu2 63.3(6) . 2_765 ? O3 C7 Eu2 61.7(5) . 2_765 ? C5 C7 Eu2 161.1(7) . 2_765 ? N2 C8 C9 121.3(9) . . ? N2 C8 C13 113.2(8) . . ? C9 C8 C13 125.5(8) . . ? C8 C9 C10 120.6(9) . . ? C8 C9 H9A 119.7 . . ? C10 C9 H9A 119.7 . . ? C9 C10 C11 117.4(10) . . ? C9 C10 H10A 121.3 . . ? C11 C10 H10A 121.3 . . ? C12 C11 C10 119.5(9) . . ? C12 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? N2 C12 C11 121.5(9) . . ? N2 C12 C14 114.9(8) . . ? C11 C12 C14 123.4(9) . . ? O6 C13 O5 125.3(9) . . ? O6 C13 C8 118.9(8) . . ? O5 C13 C8 115.9(8) . . ? O8 C14 O7 120.1(8) . . ? O8 C14 C12 122.9(9) . . ? O7 C14 C12 117.0(8) . . ? O8 C14 Eu2 58.8(5) . . ? O7 C14 Eu2 61.5(4) . . ? C12 C14 Eu2 175.5(7) . . ? N3 C15 C16 123.7(11) . . ? N3 C15 C20 113.4(9) . . ? C16 C15 C20 122.9(11) . . ? C15 C16 C17 118.0(13) . . ? C15 C16 H16A 121.0 . . ? C17 C16 H16A 121.0 . . ? C18 C17 C16 119.1(13) . . ? C18 C17 H17A 120.4 . . ? C16 C17 H17A 120.4 . . ? C17 C18 C19 119.4(12) . . ? C17 C18 H18A 120.3 . . ? C19 C18 H18A 120.3 . . ? N3 C19 C18 120.8(13) . . ? N3 C19 H19A 119.6 . . ? C18 C19 H19A 119.6 . . ? O15 C20 O16 123.9(10) . . ? O15 C20 C15 120.3(9) . . ? O16 C20 C15 115.7(9) . . ? 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 O13 H13A O6 0.85 2.04 2.747(10) 139.9 1_455 O14 H14A O5 0.85 2.19 2.795(10) 127.8 2_765 O14 H14B O11 0.85 2.25 3.007(9) 148.3 2_665 O14 H14B O12 0.85 2.39 3.130(10) 145.9 2_665 O14 H14B S 0.85 2.84 3.678(7) 170.1 2_665 O17 H17B O16 0.85 1.96 2.794(11) 167.2 2_666 O17 H17C O1 0.85 2.00 2.771(10) 150.9 . O17 H17C O7 0.85 2.64 3.181(10) 122.6 . _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 3.330 _refine_diff_density_min -1.699 _refine_diff_density_rms 0.334 data_1_778105 _database_code_depnum_ccdc_archive 'CCDC 778105' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cu0.50 N3 Nd2 O17 S' _chemical_formula_weight 922.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.510 _cell_length_b 10.9229(4) _cell_length_c 13.02500(10) _cell_angle_alpha 88.851(7) _cell_angle_beta 66.903(5) _cell_angle_gamma 80.450(7) _cell_volume 1354.66(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3387 _cell_measurement_theta_min 2.1392 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Prism _exptl_crystal_colour Light-blue _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.1800 _exptl_crystal_size_min 0.1100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 887 _exptl_absorpt_coefficient_mu 4.337 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.437 _exptl_absorpt_correction_T_max 0.621 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'SCXmini CCD' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10714 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0871 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5978 _reflns_number_gt 4987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+1.9493P] 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 SHELXL _refine_ls_extinction_coef 0.0079(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5978 _refine_ls_number_parameters 395 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1730 _refine_ls_wR_factor_gt 0.1567 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 Nd1 Nd 0.48312(4) 1.11517(4) 0.13252(3) 0.02467(17) Uani 1 1 d . . . Nd2 Nd 0.09964(4) 0.89952(4) 0.19043(3) 0.02673(17) Uani 1 1 d . . . Cu Cu 0.0000 0.5000 0.5000 0.0459(4) Uani 1 2 d S . . S S 0.2510(2) 1.15909(18) 0.03219(16) 0.0276(4) Uani 1 1 d . . . O1 O 0.3581(6) 1.2284(5) 0.3118(4) 0.0338(13) Uani 1 1 d . . . O2 O 0.2587(8) 1.4060(7) 0.4156(6) 0.060(2) Uani 1 1 d . . . O3 O 0.6598(6) 1.1910(5) -0.0358(4) 0.0292(11) Uani 1 1 d . . . O4 O 0.7834(7) 1.3327(6) -0.1277(5) 0.0449(16) Uani 1 1 d . . . O5 O 0.7038(6) 1.0974(5) 0.1635(5) 0.0351(13) Uani 1 1 d . . . O6 O 0.8622(6) 0.9968(6) 0.2237(5) 0.0390(14) Uani 1 1 d . . . O7 O 0.2973(5) 0.9840(5) 0.2236(4) 0.0311(12) Uani 1 1 d . . . O8 O 0.2227(7) 0.8234(6) 0.3210(6) 0.0465(17) Uani 1 1 d . . . O9 O 0.3911(6) 1.0709(5) -0.0157(5) 0.0338(13) Uani 1 1 d . . . O10 O 0.2673(6) 1.2371(5) 0.1153(5) 0.0366(14) Uani 1 1 d . . . O11 O 0.1409(6) 1.0826(5) 0.0877(5) 0.0352(13) Uani 1 1 d . . . O12 O 0.2209(7) 1.2283(6) -0.0525(5) 0.0430(15) Uani 1 1 d . . . O13 O -0.0118(7) 1.0314(7) 0.3678(6) 0.0494(18) Uani 1 1 d . . . H13A H -0.0059 1.0407 0.3013 0.059 Uiso 1 1 d R . . H13B H -0.0844 1.0804 0.4107 0.059 Uiso 1 1 d R . . O14 O 0.0646(6) 0.8432(6) 0.0195(5) 0.0429(15) Uani 1 1 d . . . H14A H 0.1433 0.8137 -0.0319 0.052 Uiso 1 1 d R . . H14B H 0.0009 0.8356 -0.0035 0.052 Uiso 1 1 d R . . O15 O -0.0421(6) 0.7545(6) 0.2943(5) 0.0409(14) Uani 1 1 d . . . O16 O 0.0141(7) 0.6524(6) 0.4241(5) 0.0414(15) Uani 1 1 d . . . O17 O 0.1395(7) 1.1230(6) 0.4606(5) 0.0451(16) Uani 1 1 d . . . H17B H 0.1034 1.1964 0.4886 0.054 Uiso 1 1 d R . . H17C H 0.2163 1.1266 0.4056 0.054 Uiso 1 1 d R . . N1 N 0.5155(7) 1.3413(6) 0.1421(5) 0.0293(14) Uani 1 1 d . . . N2 N 0.5190(7) 0.9582(6) 0.2749(5) 0.0268(13) Uani 1 1 d . . . N3 N -0.0439(9) 0.4462(7) 0.3733(7) 0.0454(18) Uani 1 1 d . . . C1 C 0.4381(10) 1.4140(9) 0.2357(7) 0.041(2) Uani 1 1 d . . . C2 C 0.4477(11) 1.5351(9) 0.2415(8) 0.048(2) Uani 1 1 d . . . H2A H 0.3879 1.5847 0.3046 0.057 Uiso 1 1 calc R . . C3 C 0.5444(11) 1.5848(9) 0.1555(9) 0.050(2) Uani 1 1 d . . . H3A H 0.5554 1.6666 0.1621 0.060 Uiso 1 1 calc R . . C4 C 0.6278(10) 1.5125(9) 0.0567(8) 0.041(2) Uani 1 1 d . . . H4A H 0.6924 1.5447 -0.0046 0.049 Uiso 1 1 calc R . . C5 C 0.6078(8) 1.3897(7) 0.0559(6) 0.0284(16) Uani 1 1 d . . . C6 C 0.3411(9) 1.3449(9) 0.3299(7) 0.0373(19) Uani 1 1 d . . . C7 C 0.6902(8) 1.3012(7) -0.0444(6) 0.0299(17) Uani 1 1 d . . . C8 C 0.6324(8) 0.9514(7) 0.3002(6) 0.0295(16) Uani 1 1 d . . . C9 C 0.6454(9) 0.8840(9) 0.3870(7) 0.040(2) Uani 1 1 d . . . H9A H 0.7237 0.8822 0.4041 0.048 Uiso 1 1 calc R . . C10 C 0.5390(9) 0.8185(10) 0.4490(7) 0.045(2) Uani 1 1 d . . . H10A H 0.5442 0.7746 0.5095 0.054 Uiso 1 1 calc R . . C11 C 0.4250(9) 0.8192(9) 0.4195(7) 0.041(2) Uani 1 1 d . . . H11A H 0.3555 0.7723 0.4565 0.049 Uiso 1 1 calc R . . C12 C 0.4194(9) 0.8926(8) 0.3329(7) 0.0324(18) Uani 1 1 d . . . C13 C 0.7421(8) 1.0195(7) 0.2229(6) 0.0294(16) Uani 1 1 d . . . C14 C 0.3052(9) 0.8958(8) 0.2909(7) 0.0307(17) Uani 1 1 d . . . C15 C -0.0496(10) 0.5409(10) 0.3044(8) 0.044(2) Uani 1 1 d . . . C16 C -0.0829(13) 0.5275(11) 0.2147(9) 0.061(3) Uani 1 1 d . . . H16A H -0.0880 0.5931 0.1690 0.073 Uiso 1 1 calc R . . C17 C -0.1090(13) 0.4108(12) 0.1943(11) 0.068(3) Uani 1 1 d . . . H17A H -0.1333 0.3990 0.1342 0.082 Uiso 1 1 calc R . . C18 C -0.1001(13) 0.3163(11) 0.2583(10) 0.062(3) Uani 1 1 d . . . H18A H -0.1124 0.2380 0.2412 0.074 Uiso 1 1 calc R . . C19 C -0.0714(12) 0.3380(10) 0.3532(10) 0.060(3) Uani 1 1 d . . . H19A H -0.0719 0.2747 0.4022 0.072 Uiso 1 1 calc R . . C20 C -0.0238(9) 0.6591(8) 0.3411(7) 0.037(2) 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 Nd1 0.0244(3) 0.0254(3) 0.0272(3) 0.00343(16) -0.01282(19) -0.00579(17) Nd2 0.0240(3) 0.0302(3) 0.0291(3) 0.00545(17) -0.01337(19) -0.00605(18) Cu 0.0542(10) 0.0473(10) 0.0385(8) -0.0003(7) -0.0163(8) -0.0198(8) S 0.0271(10) 0.0239(9) 0.0361(10) 0.0058(7) -0.0172(8) -0.0045(7) O1 0.044(3) 0.031(3) 0.029(3) 0.003(2) -0.015(3) -0.010(3) O2 0.063(5) 0.042(4) 0.050(4) -0.019(3) 0.005(3) -0.005(3) O3 0.030(3) 0.029(3) 0.027(3) 0.003(2) -0.009(2) -0.007(2) O4 0.038(4) 0.038(4) 0.043(3) 0.015(3) 0.000(3) -0.008(3) O5 0.033(3) 0.033(3) 0.044(3) 0.013(2) -0.019(3) -0.007(2) O6 0.026(3) 0.044(4) 0.051(4) 0.011(3) -0.020(3) -0.007(3) O7 0.023(3) 0.037(3) 0.035(3) 0.008(2) -0.013(2) -0.008(2) O8 0.048(4) 0.047(4) 0.063(4) 0.032(3) -0.036(3) -0.028(3) O9 0.027(3) 0.035(3) 0.039(3) -0.002(2) -0.015(2) 0.001(2) O10 0.037(3) 0.030(3) 0.047(3) -0.005(2) -0.024(3) 0.002(2) O11 0.027(3) 0.037(3) 0.044(3) 0.007(2) -0.015(3) -0.010(2) O12 0.049(4) 0.045(4) 0.048(4) 0.019(3) -0.032(3) -0.011(3) O13 0.045(4) 0.065(5) 0.041(4) -0.008(3) -0.022(3) -0.002(3) O14 0.033(3) 0.064(5) 0.038(3) 0.003(3) -0.020(3) -0.010(3) O15 0.032(3) 0.031(3) 0.048(4) 0.007(3) -0.003(3) -0.008(3) O16 0.049(4) 0.038(4) 0.037(3) -0.004(3) -0.020(3) -0.002(3) O17 0.058(4) 0.041(4) 0.032(3) -0.004(3) -0.014(3) -0.008(3) N1 0.032(4) 0.028(3) 0.030(3) -0.003(2) -0.017(3) -0.001(3) N2 0.024(3) 0.028(3) 0.032(3) 0.006(2) -0.012(3) -0.010(3) N3 0.056(5) 0.034(4) 0.050(4) 0.000(3) -0.025(4) -0.009(4) C1 0.039(5) 0.040(5) 0.036(4) -0.005(4) -0.006(4) -0.004(4) C2 0.052(6) 0.038(5) 0.048(5) -0.005(4) -0.015(5) -0.006(4) C3 0.057(6) 0.029(5) 0.062(6) -0.001(4) -0.021(5) -0.011(4) C4 0.038(5) 0.035(5) 0.048(5) 0.007(4) -0.012(4) -0.017(4) C5 0.029(4) 0.024(4) 0.031(4) 0.007(3) -0.010(3) -0.006(3) C6 0.036(5) 0.047(5) 0.032(4) 0.001(4) -0.015(4) -0.010(4) C7 0.028(4) 0.030(4) 0.034(4) 0.006(3) -0.015(3) -0.005(3) C8 0.029(4) 0.032(4) 0.027(4) 0.004(3) -0.010(3) -0.006(3) C9 0.027(4) 0.054(6) 0.046(5) 0.013(4) -0.021(4) -0.007(4) C10 0.032(5) 0.073(7) 0.033(4) 0.028(4) -0.016(4) -0.015(4) C11 0.037(5) 0.050(6) 0.040(5) 0.017(4) -0.018(4) -0.014(4) C12 0.030(4) 0.037(5) 0.033(4) -0.001(3) -0.014(3) -0.008(3) C13 0.028(4) 0.031(4) 0.030(4) -0.007(3) -0.013(3) -0.004(3) C14 0.035(4) 0.036(4) 0.029(4) 0.008(3) -0.018(3) -0.013(3) C15 0.045(5) 0.046(5) 0.037(5) 0.008(4) -0.011(4) -0.013(4) C16 0.092(9) 0.050(6) 0.056(6) 0.005(5) -0.045(6) -0.012(6) C17 0.079(9) 0.062(8) 0.083(8) -0.012(6) -0.054(7) -0.006(6) C18 0.075(8) 0.043(6) 0.083(8) 0.006(5) -0.048(7) -0.007(5) C19 0.070(8) 0.044(6) 0.075(7) 0.000(5) -0.039(6) -0.007(5) C20 0.036(5) 0.037(5) 0.027(4) 0.003(3) -0.004(3) 0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Nd1 O9 2.418(6) 2_675 ? Nd1 O1 2.425(5) . ? Nd1 O5 2.482(6) . ? Nd1 O3 2.487(5) . ? Nd1 O7 2.513(6) . ? Nd1 O10 2.521(5) . ? Nd1 O9 2.560(6) . ? Nd1 N1 2.561(7) . ? Nd1 N2 2.594(6) . ? Nd1 S 3.1585(18) . ? Nd2 O15 2.382(6) . ? Nd2 O11 2.388(6) . ? Nd2 O6 2.416(5) 1_455 ? Nd2 O13 2.497(7) . ? Nd2 O14 2.499(6) . ? Nd2 O8 2.563(6) . ? Nd2 O3 2.585(5) 2_675 ? Nd2 O7 2.590(5) . ? Nd2 O4 2.621(6) 2_675 ? Nd2 C14 2.927(8) . ? Nd2 C7 2.927(8) 2_675 ? Nd2 H13A 1.9890 . ? Cu O16 1.917(7) 2_566 ? Cu O16 1.917(7) . ? Cu N3 2.002(8) 2_566 ? Cu N3 2.002(8) . ? S O12 1.432(6) . ? S O10 1.469(6) . ? S O11 1.484(6) . ? S O9 1.522(6) . ? O1 C6 1.269(11) . ? O2 C6 1.234(10) . ? O3 C7 1.287(10) . ? O3 Nd2 2.585(5) 2_675 ? O4 C7 1.232(10) . ? O4 Nd2 2.621(6) 2_675 ? O5 C13 1.260(9) . ? O6 C13 1.250(9) . ? O6 Nd2 2.416(5) 1_655 ? O7 C14 1.304(9) . ? O8 C14 1.216(10) . ? O9 Nd1 2.418(5) 2_675 ? O13 H13A 0.8500 . ? O13 H13B 0.8500 . ? O14 H14A 0.8500 . ? O14 H14B 0.8501 . ? O15 C20 1.223(10) . ? O16 C20 1.287(10) . ? O17 H17B 0.8500 . ? O17 H17C 0.8500 . ? N1 C5 1.331(10) . ? N1 C1 1.351(10) . ? N2 C12 1.337(11) . ? N2 C8 1.347(10) . ? N3 C19 1.317(13) . ? N3 C15 1.366(12) . ? C1 C2 1.349(13) . ? C1 C6 1.534(13) . ? C2 C3 1.360(14) . ? C2 H2A 0.9300 . ? C3 C4 1.405(13) . ? C3 H3A 0.9300 . ? C4 C5 1.392(12) . ? C4 H4A 0.9300 . ? C5 C7 1.509(11) . ? C7 Nd2 2.927(8) 2_675 ? C8 C9 1.376(11) . ? C8 C13 1.497(11) . ? C9 C10 1.396(13) . ? C9 H9A 0.9300 . ? C10 C11 1.392(12) . ? C10 H10A 0.9300 . ? C11 C12 1.386(11) . ? C11 H11A 0.9300 . ? C12 C14 1.497(11) . ? C15 C16 1.361(13) . ? C15 C20 1.487(14) . ? C16 C17 1.400(16) . ? C16 H16A 0.9300 . ? C17 C18 1.328(16) . ? C17 H17A 0.9300 . ? C18 C19 1.415(15) . ? C18 H18A 0.9300 . ? C19 H19A 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 O9 Nd1 O1 153.08(19) 2_675 . ? O9 Nd1 O5 81.99(19) 2_675 . ? O1 Nd1 O5 89.1(2) . . ? O9 Nd1 O3 75.73(19) 2_675 . ? O1 Nd1 O3 125.71(19) . . ? O5 Nd1 O3 72.70(18) . . ? O9 Nd1 O7 83.9(2) 2_675 . ? O1 Nd1 O7 80.20(19) . . ? O5 Nd1 O7 124.21(17) . . ? O3 Nd1 O7 151.59(18) . . ? O9 Nd1 O10 120.57(18) 2_675 . ? O1 Nd1 O10 76.36(19) . . ? O5 Nd1 O10 153.02(19) . . ? O3 Nd1 O10 97.27(19) . . ? O7 Nd1 O10 76.14(19) . . ? O9 Nd1 O9 65.9(2) 2_675 . ? O1 Nd1 O9 128.80(19) . . ? O5 Nd1 O9 141.74(18) . . ? O3 Nd1 O9 79.44(18) . . ? O7 Nd1 O9 74.19(18) . . ? O10 Nd1 O9 54.96(17) . . ? O9 Nd1 N1 137.3(2) 2_675 . ? O1 Nd1 N1 63.2(2) . . ? O5 Nd1 N1 76.46(19) . . ? O3 Nd1 N1 62.87(19) . . ? O7 Nd1 N1 138.5(2) . . ? O10 Nd1 N1 76.7(2) . . ? O9 Nd1 N1 113.30(19) . . ? O9 Nd1 N2 77.4(2) 2_675 . ? O1 Nd1 N2 75.99(19) . . ? O5 Nd1 N2 62.13(19) . . ? O3 Nd1 N2 129.81(19) . . ? O7 Nd1 N2 62.14(18) . . ? O10 Nd1 N2 132.9(2) . . ? O9 Nd1 N2 125.0(2) . . ? N1 Nd1 N2 121.4(2) . . ? O9 Nd1 S 93.50(14) 2_675 . ? O1 Nd1 S 100.75(15) . . ? O5 Nd1 S 165.23(14) . . ? O3 Nd1 S 92.57(13) . . ? O7 Nd1 S 68.84(12) . . ? O10 Nd1 S 27.11(13) . . ? O9 Nd1 S 28.50(12) . . ? N1 Nd1 S 98.10(14) . . ? N2 Nd1 S 130.75(14) . . ? O15 Nd2 O11 154.2(2) . . ? O15 Nd2 O6 75.4(2) . 1_455 ? O11 Nd2 O6 79.2(2) . 1_455 ? O15 Nd2 O13 84.9(2) . . ? O11 Nd2 O13 89.4(2) . . ? O6 Nd2 O13 68.1(2) 1_455 . ? O15 Nd2 O14 90.8(2) . . ? O11 Nd2 O14 78.7(2) . . ? O6 Nd2 O14 75.1(2) 1_455 . ? O13 Nd2 O14 142.8(2) . . ? O15 Nd2 O8 78.9(2) . . ? O11 Nd2 O8 122.72(19) . . ? O6 Nd2 O8 133.0(2) 1_455 . ? O13 Nd2 O8 70.9(2) . . ? O14 Nd2 O8 144.2(2) . . ? O15 Nd2 O3 116.92(19) . 2_675 ? O11 Nd2 O3 82.02(18) . 2_675 ? O6 Nd2 O3 143.62(19) 1_455 2_675 ? O13 Nd2 O3 142.6(2) . 2_675 ? O14 Nd2 O3 70.87(18) . 2_675 ? O8 Nd2 O3 83.33(19) . 2_675 ? O15 Nd2 O7 129.0(2) . . ? O11 Nd2 O7 72.13(18) . . ? O6 Nd2 O7 130.8(2) 1_455 . ? O13 Nd2 O7 72.4(2) . . ? O14 Nd2 O7 133.87(19) . . ? O8 Nd2 O7 50.81(17) . . ? O3 Nd2 O7 70.30(17) 2_675 . ? O15 Nd2 O4 66.68(19) . 2_675 ? O11 Nd2 O4 129.35(19) . 2_675 ? O6 Nd2 O4 127.8(2) 1_455 2_675 ? O13 Nd2 O4 137.8(2) . 2_675 ? O14 Nd2 O4 71.1(2) . 2_675 ? O8 Nd2 O4 73.3(2) . 2_675 ? O3 Nd2 O4 50.24(18) 2_675 2_675 ? O7 Nd2 O4 101.2(2) . 2_675 ? O15 Nd2 C14 103.3(2) . . ? O11 Nd2 C14 98.6(2) . . ? O6 Nd2 C14 139.2(2) 1_455 . ? O13 Nd2 C14 71.2(2) . . ? O14 Nd2 C14 145.0(2) . . ? O8 Nd2 C14 24.4(2) . . ? O3 Nd2 C14 74.2(2) 2_675 . ? O7 Nd2 C14 26.5(2) . . ? O4 Nd2 C14 85.2(2) 2_675 . ? O15 Nd2 C7 91.2(2) . 2_675 ? O11 Nd2 C7 105.0(2) . 2_675 ? O6 Nd2 C7 137.2(2) 1_455 2_675 ? O13 Nd2 C7 152.2(2) . 2_675 ? O14 Nd2 C7 64.5(2) . 2_675 ? O8 Nd2 C7 81.3(2) . 2_675 ? O3 Nd2 C7 26.1(2) 2_675 2_675 ? O7 Nd2 C7 89.3(2) . 2_675 ? O4 Nd2 C7 24.9(2) 2_675 2_675 ? C14 Nd2 C7 83.0(2) . 2_675 ? O15 Nd2 H13A 94.4 . . ? O11 Nd2 H13A 74.6 . . ? O6 Nd2 H13A 56.7 1_455 . ? O13 Nd2 H13A 17.6 . . ? O14 Nd2 H13A 128.0 . . ? O8 Nd2 H13A 87.3 . . ? O3 Nd2 H13A 144.6 2_675 . ? O7 Nd2 H13A 77.3 . . ? O4 Nd2 H13A 154.8 2_675 . ? C14 Nd2 H13A 83.2 . . ? C7 Nd2 H13A 166.1 2_675 . ? O16 Cu O16 180.000(1) 2_566 . ? O16 Cu N3 82.8(3) 2_566 2_566 ? O16 Cu N3 97.2(3) . 2_566 ? O16 Cu N3 97.2(3) 2_566 . ? O16 Cu N3 82.8(3) . . ? N3 Cu N3 180.000(1) 2_566 . ? O12 S O10 113.5(4) . . ? O12 S O11 109.9(4) . . ? O10 S O11 110.5(4) . . ? O12 S O9 112.1(4) . . ? O10 S O9 103.2(3) . . ? O11 S O9 107.3(3) . . ? O12 S Nd1 139.4(3) . . ? O10 S Nd1 51.5(2) . . ? O11 S Nd1 110.7(2) . . ? O9 S Nd1 53.4(2) . . ? C6 O1 Nd1 126.4(5) . . ? C7 O3 Nd1 125.1(5) . . ? C7 O3 Nd2 92.0(4) . 2_675 ? Nd1 O3 Nd2 137.0(2) . 2_675 ? C7 O4 Nd2 91.6(5) . 2_675 ? C13 O5 Nd1 125.7(5) . . ? C13 O6 Nd2 162.7(6) . 1_655 ? C14 O7 Nd1 124.8(5) . . ? C14 O7 Nd2 91.3(5) . . ? Nd1 O7 Nd2 140.4(2) . . ? C14 O8 Nd2 94.8(5) . . ? S O9 Nd1 144.5(3) . 2_675 ? S O9 Nd1 98.2(3) . . ? Nd1 O9 Nd1 114.1(2) 2_675 . ? S O10 Nd1 101.4(3) . . ? S O11 Nd2 142.3(3) . . ? Nd2 O13 H13A 45.0 . . ? Nd2 O13 H13B 146.0 . . ? H13A O13 H13B 107.7 . . ? Nd2 O14 H14A 109.8 . . ? Nd2 O14 H14B 142.1 . . ? H14A O14 H14B 107.7 . . ? C20 O15 Nd2 136.0(6) . . ? C20 O16 Cu 115.9(6) . . ? H17B O17 H17C 107.7 . . ? C5 N1 C1 118.8(7) . . ? C5 N1 Nd1 121.2(5) . . ? C1 N1 Nd1 120.1(6) . . ? C12 N2 C8 118.6(7) . . ? C12 N2 Nd1 121.0(5) . . ? C8 N2 Nd1 120.0(5) . . ? C19 N3 C15 119.4(9) . . ? C19 N3 Cu 128.9(7) . . ? C15 N3 Cu 111.6(6) . . ? C2 C1 N1 121.5(9) . . ? C2 C1 C6 125.3(8) . . ? N1 C1 C6 113.2(8) . . ? C1 C2 C3 120.3(9) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.8 . . ? C2 C3 C4 119.9(9) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 116.0(8) . . ? C5 C4 H4A 122.0 . . ? C3 C4 H4A 122.0 . . ? N1 C5 C4 123.2(7) . . ? N1 C5 C7 114.9(7) . . ? C4 C5 C7 121.8(7) . . ? O2 C6 O1 126.9(9) . . ? O2 C6 C1 117.7(9) . . ? O1 C6 C1 115.4(7) . . ? O4 C7 O3 122.7(7) . . ? O4 C7 C5 121.4(8) . . ? O3 C7 C5 115.9(7) . . ? O4 C7 Nd2 63.5(4) . 2_675 ? O3 C7 Nd2 62.0(4) . 2_675 ? C5 C7 Nd2 160.5(5) . 2_675 ? N2 C8 C9 122.0(8) . . ? N2 C8 C13 113.5(6) . . ? C9 C8 C13 124.4(7) . . ? C8 C9 C10 118.8(8) . . ? C8 C9 H9A 120.6 . . ? C10 C9 H9A 120.6 . . ? C11 C10 C9 119.6(8) . . ? C11 C10 H10A 120.2 . . ? C9 C10 H10A 120.2 . . ? C12 C11 C10 117.2(8) . . ? C12 C11 H11A 121.4 . . ? C10 C11 H11A 121.4 . . ? N2 C12 C11 123.5(8) . . ? N2 C12 C14 114.6(7) . . ? C11 C12 C14 121.7(8) . . ? O6 C13 O5 125.4(8) . . ? O6 C13 C8 118.0(7) . . ? O5 C13 C8 116.5(7) . . ? O8 C14 O7 122.6(7) . . ? O8 C14 C12 121.9(7) . . ? O7 C14 C12 115.5(7) . . ? O8 C14 Nd2 60.7(4) . . ? O7 C14 Nd2 62.2(4) . . ? C12 C14 Nd2 175.3(6) . . ? C16 C15 N3 122.2(10) . . ? C16 C15 C20 124.5(9) . . ? N3 C15 C20 113.3(8) . . ? C15 C16 C17 117.0(10) . . ? C15 C16 H16A 121.5 . . ? C17 C16 H16A 121.5 . . ? C18 C17 C16 121.8(11) . . ? C18 C17 H17A 119.1 . . ? C16 C17 H17A 119.1 . . ? C17 C18 C19 118.3(11) . . ? C17 C18 H18A 120.9 . . ? C19 C18 H18A 120.9 . . ? N3 C19 C18 121.1(11) . . ? N3 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? O15 C20 O16 124.6(9) . . ? O15 C20 C15 119.7(8) . . ? O16 C20 C15 115.7(8) . . ? 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 O13 H13A O6 0.85 2.12 2.751(9) 130.3 1_455 O14 H14A O5 0.85 2.18 2.818(8) 131.7 2_675 O14 H14B O11 0.85 2.24 3.002(8) 149.1 2_575 O14 H14B O12 0.85 2.37 3.090(9) 142.2 2_575 O14 H14B S 0.85 2.81 3.638(6) 166.6 2_575 O17 H17B O16 0.85 1.96 2.795(9) 167.0 2_576 O17 H17C O1 0.85 2.00 2.767(9) 148.9 . O17 H17C O7 0.85 2.63 3.150(8) 121.0 . _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 4.424 _refine_diff_density_min -1.848 _refine_diff_density_rms 0.316 # Attachment '10051429.cif' data_1c_778326 _database_code_depnum_ccdc_archive 'CCDC 778326' #TrackingRef '10051429.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cu0.50 Gd2 N3 O17 S' _chemical_formula_weight 948.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.426 _cell_length_b 10.8303(3) _cell_length_c 12.97990(10) _cell_angle_alpha 88.649(7) _cell_angle_beta 66.992(5) _cell_angle_gamma 80.223(5) _cell_volume 1328.03(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3383 _cell_measurement_theta_min 2.1551 _cell_measurement_theta_max 27.4797 _exptl_crystal_description Prism _exptl_crystal_colour Light-blue _exptl_crystal_size_max 0.1200 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0800 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 903 _exptl_absorpt_coefficient_mu 5.508 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.522 _exptl_absorpt_correction_T_max 0.644 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'SCXmini CCD' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10533 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5861 _reflns_number_gt 5193 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+7.4739P] 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 SHELXL _refine_ls_extinction_coef 0.0097(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5861 _refine_ls_number_parameters 395 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 Gd1 Gd 0.98487(4) 1.11307(3) 0.13122(3) 0.02220(16) Uani 1 1 d . . . Gd2 Gd 0.60134(4) 0.90139(4) 0.18916(3) 0.02480(16) Uani 1 1 d . . . Cu Cu 0.5000 0.5000 0.5000 0.0470(5) Uani 1 2 d S . . S S 0.7526(2) 1.15943(18) 0.03205(17) 0.0257(4) Uani 1 1 d . . . O1 O 0.8602(7) 1.2203(5) 0.3098(5) 0.0323(14) Uani 1 1 d . . . O2 O 0.7585(9) 1.3972(7) 0.4165(6) 0.058(2) Uani 1 1 d . . . O3 O 1.1601(6) 1.1855(5) -0.0352(5) 0.0271(12) Uani 1 1 d . . . O4 O 1.2837(7) 1.3298(6) -0.1290(5) 0.0404(16) Uani 1 1 d . . . O5 O 1.2047(6) 1.0984(6) 0.1589(5) 0.0321(13) Uani 1 1 d . . . O6 O 1.3664(6) 0.9984(6) 0.2185(5) 0.0351(14) Uani 1 1 d . . . O7 O 0.7990(6) 0.9850(5) 0.2193(5) 0.0259(12) Uani 1 1 d . . . O8 O 0.7230(7) 0.8228(6) 0.3157(6) 0.0415(16) Uani 1 1 d . . . O9 O 0.8929(6) 1.0716(5) -0.0166(5) 0.0297(13) Uani 1 1 d . . . O10 O 0.7694(6) 1.2359(5) 0.1165(5) 0.0304(13) Uani 1 1 d . . . O11 O 0.6411(7) 1.0823(5) 0.0859(5) 0.0329(13) Uani 1 1 d . . . O12 O 0.7222(7) 1.2309(6) -0.0524(6) 0.0404(15) Uani 1 1 d . . . O13 O 0.4916(8) 1.0297(7) 0.3613(6) 0.0489(19) Uani 1 1 d . . . H13A H 0.4631 1.0148 0.3105 0.059 Uiso 1 1 d R . . H13B H 0.4244 1.0776 0.4117 0.059 Uiso 1 1 d R . . O14 O 0.5639(7) 0.8461(6) 0.0239(5) 0.0387(15) Uani 1 1 d . . . H14A H 0.6401 0.8141 -0.0297 0.046 Uiso 1 1 d R . . H14B H 0.4953 0.8363 0.0068 0.046 Uiso 1 1 d R . . O15 O 0.4615(7) 0.7597(6) 0.2931(6) 0.0408(15) Uani 1 1 d . . . O16 O 0.5174(8) 0.6553(6) 0.4237(6) 0.0428(16) Uani 1 1 d . . . O17 O 0.6388(9) 1.1195(6) 0.4603(6) 0.0501(19) Uani 1 1 d . . . H17B H 0.6021 1.1931 0.4894 0.060 Uiso 1 1 d R . . H17C H 0.7169 1.1239 0.4062 0.060 Uiso 1 1 d R . . N1 N 1.0164(8) 1.3356(6) 0.1402(6) 0.0266(14) Uani 1 1 d . . . N2 N 1.0207(7) 0.9597(6) 0.2716(5) 0.0244(14) Uani 1 1 d . . . N3 N 0.4557(10) 0.4483(7) 0.3721(8) 0.046(2) Uani 1 1 d . . . C1 C 0.9381(11) 1.4079(8) 0.2355(7) 0.035(2) Uani 1 1 d . . . C2 C 0.9465(12) 1.5317(9) 0.2441(9) 0.047(3) Uani 1 1 d . . . H2A H 0.8881 1.5806 0.3086 0.057 Uiso 1 1 calc R . . C3 C 1.0442(13) 1.5828(9) 0.1543(9) 0.049(3) Uani 1 1 d . . . H3A H 1.0529 1.6664 0.1589 0.059 Uiso 1 1 calc R . . C4 C 1.1277(11) 1.5098(9) 0.0591(8) 0.038(2) Uani 1 1 d . . . H4A H 1.1960 1.5419 -0.0004 0.045 Uiso 1 1 calc R . . C5 C 1.1081(9) 1.3869(8) 0.0536(7) 0.0286(17) Uani 1 1 d . . . C6 C 0.8409(10) 1.3374(8) 0.3294(7) 0.0338(19) Uani 1 1 d . . . C7 C 1.1888(9) 1.2991(7) -0.0442(7) 0.0262(16) Uani 1 1 d . . . C8 C 1.1342(9) 0.9515(7) 0.2977(7) 0.0261(16) Uani 1 1 d . . . C9 C 1.1489(11) 0.8823(9) 0.3860(8) 0.036(2) Uani 1 1 d . . . H9A H 1.2279 0.8797 0.4033 0.043 Uiso 1 1 calc R . . C10 C 1.0412(11) 0.8178(9) 0.4465(9) 0.042(2) Uani 1 1 d . . . H10A H 1.0454 0.7730 0.5075 0.051 Uiso 1 1 calc R . . C11 C 0.9277(10) 0.8198(10) 0.4166(8) 0.039(2) Uani 1 1 d . . . H11A H 0.8574 0.7732 0.4546 0.046 Uiso 1 1 calc R . . C12 C 0.9200(10) 0.8918(7) 0.3296(6) 0.0269(17) Uani 1 1 d . . . C13 C 1.2454(9) 1.0208(7) 0.2205(7) 0.0268(17) Uani 1 1 d . . . C14 C 0.8073(9) 0.8983(7) 0.2875(7) 0.0265(17) Uani 1 1 d . . . C15 C 0.4525(11) 0.5412(9) 0.3034(8) 0.041(2) Uani 1 1 d . . . C16 C 0.4199(15) 0.5344(11) 0.2104(10) 0.058(3) Uani 1 1 d . . . H16A H 0.4162 0.6024 0.1659 0.069 Uiso 1 1 calc R . . C17 C 0.3922(17) 0.4161(13) 0.1872(13) 0.073(4) Uani 1 1 d . . . H17A H 0.3697 0.4049 0.1259 0.088 Uiso 1 1 calc R . . C18 C 0.3988(16) 0.3176(11) 0.2561(11) 0.062(3) Uani 1 1 d . . . H18A H 0.3831 0.2394 0.2406 0.074 Uiso 1 1 calc R . . C19 C 0.4293(15) 0.3377(11) 0.3484(12) 0.064(3) Uani 1 1 d . . . H19A H 0.4316 0.2722 0.3957 0.076 Uiso 1 1 calc R . . C20 C 0.4794(11) 0.6620(9) 0.3401(7) 0.037(2) 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 Gd1 0.0219(3) 0.0221(2) 0.0246(2) 0.00191(15) -0.01120(18) -0.00412(15) Gd2 0.0219(3) 0.0283(2) 0.0264(2) 0.00353(16) -0.01200(19) -0.00450(16) Cu 0.0489(11) 0.0585(11) 0.0345(9) 0.0002(8) -0.0139(8) -0.0174(9) S 0.0243(11) 0.0237(9) 0.0332(10) 0.0034(8) -0.0162(9) -0.0030(8) O1 0.040(4) 0.027(3) 0.025(3) 0.000(2) -0.006(3) -0.009(3) O2 0.063(5) 0.043(4) 0.044(4) -0.010(3) 0.005(4) -0.008(4) O3 0.027(3) 0.026(3) 0.028(3) 0.001(2) -0.011(2) -0.002(2) O4 0.037(4) 0.035(3) 0.038(4) 0.006(3) -0.002(3) -0.008(3) O5 0.028(3) 0.033(3) 0.041(3) 0.009(3) -0.017(3) -0.012(3) O6 0.020(3) 0.042(3) 0.046(4) 0.005(3) -0.017(3) -0.002(3) O7 0.026(3) 0.030(3) 0.024(3) 0.005(2) -0.011(2) -0.007(2) O8 0.043(4) 0.047(4) 0.052(4) 0.026(3) -0.032(3) -0.027(3) O9 0.021(3) 0.032(3) 0.035(3) -0.002(2) -0.011(3) -0.002(2) O10 0.027(3) 0.027(3) 0.039(3) -0.006(2) -0.017(3) 0.002(2) O11 0.031(3) 0.029(3) 0.042(3) 0.007(3) -0.017(3) -0.009(3) O12 0.041(4) 0.046(4) 0.043(4) 0.015(3) -0.027(3) -0.005(3) O13 0.043(4) 0.060(5) 0.044(4) -0.019(3) -0.022(3) 0.005(4) O14 0.029(4) 0.057(4) 0.034(3) -0.002(3) -0.018(3) -0.005(3) O15 0.032(4) 0.037(3) 0.050(4) 0.005(3) -0.011(3) -0.010(3) O16 0.054(5) 0.033(3) 0.042(4) 0.004(3) -0.019(3) -0.008(3) O17 0.060(5) 0.041(4) 0.038(4) -0.006(3) -0.008(3) -0.007(3) N1 0.029(4) 0.021(3) 0.031(4) -0.003(3) -0.015(3) 0.001(3) N2 0.024(4) 0.026(3) 0.027(3) 0.003(3) -0.012(3) -0.007(3) N3 0.053(6) 0.028(4) 0.055(5) 0.005(4) -0.022(4) -0.006(4) C1 0.045(6) 0.031(4) 0.027(4) -0.005(3) -0.012(4) -0.005(4) C2 0.055(7) 0.029(4) 0.046(6) -0.002(4) -0.009(5) -0.001(4) C3 0.067(8) 0.026(4) 0.059(7) -0.004(4) -0.028(6) -0.013(5) C4 0.034(5) 0.036(5) 0.040(5) 0.001(4) -0.009(4) -0.014(4) C5 0.026(4) 0.029(4) 0.036(4) 0.004(3) -0.015(4) -0.008(3) C6 0.033(5) 0.032(4) 0.033(5) 0.001(4) -0.010(4) -0.006(4) C7 0.022(4) 0.029(4) 0.028(4) 0.006(3) -0.009(3) -0.005(3) C8 0.024(4) 0.024(4) 0.030(4) -0.001(3) -0.013(3) 0.001(3) C9 0.040(5) 0.041(5) 0.038(5) 0.015(4) -0.027(4) -0.010(4) C10 0.044(6) 0.049(5) 0.047(5) 0.027(5) -0.029(5) -0.014(5) C11 0.024(5) 0.059(6) 0.043(5) 0.020(4) -0.019(4) -0.020(4) C12 0.038(5) 0.027(4) 0.018(4) 0.004(3) -0.013(3) -0.005(3) C13 0.021(4) 0.030(4) 0.035(4) 0.002(3) -0.016(4) -0.007(3) C14 0.029(5) 0.027(4) 0.028(4) 0.003(3) -0.014(4) -0.007(3) C15 0.039(6) 0.040(5) 0.041(5) 0.001(4) -0.013(4) -0.008(4) C16 0.080(9) 0.052(6) 0.051(7) 0.004(5) -0.034(6) -0.016(6) C17 0.094(11) 0.064(8) 0.086(10) -0.009(7) -0.063(9) -0.010(8) C18 0.090(10) 0.041(6) 0.070(8) 0.001(5) -0.047(8) -0.013(6) C19 0.081(9) 0.039(6) 0.095(10) 0.009(6) -0.058(8) -0.015(6) C20 0.036(5) 0.044(5) 0.028(4) 0.006(4) -0.011(4) 0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Gd1 O9 2.372(6) 2_775 ? Gd1 O1 2.382(6) . ? Gd1 O5 2.434(6) . ? Gd1 O3 2.437(6) . ? Gd1 O7 2.468(6) . ? Gd1 O10 2.482(6) . ? Gd1 N1 2.499(6) . ? Gd1 N2 2.530(6) . ? Gd1 O9 2.536(6) . ? Gd1 S 3.126(2) . ? Gd2 O15 2.329(7) . ? Gd2 O11 2.351(6) . ? Gd2 O6 2.380(6) 1_455 ? Gd2 O13 2.416(7) . ? Gd2 O14 2.430(6) . ? Gd2 O8 2.495(6) . ? Gd2 O3 2.545(6) 2_775 ? Gd2 O7 2.550(6) . ? Gd2 O4 2.580(6) 2_775 ? Gd2 C14 2.891(8) . ? Gd2 C7 2.899(8) 2_775 ? Gd2 H13A 1.9451 . ? Cu O16 1.931(7) . ? Cu O16 1.931(7) 2_666 ? Cu N3 2.004(9) . ? Cu N3 2.004(9) 2_666 ? S O12 1.432(6) . ? S O10 1.470(6) . ? S O11 1.484(6) . ? S O9 1.509(6) . ? O1 C6 1.265(10) . ? O2 C6 1.234(11) . ? O3 C7 1.307(10) . ? O3 Gd2 2.545(6) 2_775 ? O4 C7 1.243(10) . ? O4 Gd2 2.580(6) 2_775 ? O5 C13 1.279(10) . ? O6 C13 1.233(10) . ? O6 Gd2 2.380(6) 1_655 ? O7 C14 1.291(10) . ? O8 C14 1.246(10) . ? O9 Gd1 2.372(6) 2_775 ? O13 H13A 0.8500 . ? O13 H13B 0.8500 . ? O14 H14A 0.8500 . ? O14 H14B 0.8500 . ? O15 C20 1.232(11) . ? O16 C20 1.289(11) . ? O17 H17B 0.8500 . ? O17 H17C 0.8500 . ? N1 C5 1.341(11) . ? N1 C1 1.359(10) . ? N2 C8 1.342(10) . ? N2 C12 1.352(11) . ? N3 C15 1.334(13) . ? N3 C19 1.342(13) . ? C1 C2 1.368(13) . ? C1 C6 1.533(13) . ? C2 C3 1.391(15) . ? C2 H2A 0.9300 . ? C3 C4 1.372(14) . ? C3 H3A 0.9300 . ? C4 C5 1.388(12) . ? C4 H4A 0.9300 . ? C5 C7 1.474(12) . ? C7 Gd2 2.899(8) 2_775 ? C8 C9 1.399(11) . ? C8 C13 1.505(12) . ? C9 C10 1.385(14) . ? C9 H9A 0.9300 . ? C10 C11 1.379(13) . ? C10 H10A 0.9300 . ? C11 C12 1.378(11) . ? C11 H11A 0.9300 . ? C12 C14 1.469(12) . ? C15 C16 1.383(15) . ? C15 C20 1.508(14) . ? C16 C17 1.423(17) . ? C16 H16A 0.9300 . ? C17 C18 1.386(18) . ? C17 H17A 0.9300 . ? C18 C19 1.385(17) . ? C18 H18A 0.9300 . ? C19 H19A 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 O9 Gd1 O1 151.7(2) 2_775 . ? O9 Gd1 O5 82.7(2) 2_775 . ? O1 Gd1 O5 89.5(2) . . ? O9 Gd1 O3 75.40(19) 2_775 . ? O1 Gd1 O3 127.66(19) . . ? O5 Gd1 O3 71.53(19) . . ? O9 Gd1 O7 83.6(2) 2_775 . ? O1 Gd1 O7 79.22(19) . . ? O5 Gd1 O7 126.37(19) . . ? O3 Gd1 O7 150.62(18) . . ? O9 Gd1 O10 120.80(19) 2_775 . ? O1 Gd1 O10 76.2(2) . . ? O5 Gd1 O10 151.82(19) . . ? O3 Gd1 O10 98.0(2) . . ? O7 Gd1 O10 75.21(19) . . ? O9 Gd1 N1 137.7(2) 2_775 . ? O1 Gd1 N1 64.6(2) . . ? O5 Gd1 N1 75.6(2) . . ? O3 Gd1 N1 63.5(2) . . ? O7 Gd1 N1 138.2(2) . . ? O10 Gd1 N1 76.3(2) . . ? O9 Gd1 N2 77.8(2) 2_775 . ? O1 Gd1 N2 74.4(2) . . ? O5 Gd1 N2 63.1(2) . . ? O3 Gd1 N2 129.5(2) . . ? O7 Gd1 N2 63.3(2) . . ? O10 Gd1 N2 132.5(2) . . ? N1 Gd1 N2 121.0(2) . . ? O9 Gd1 O9 65.8(2) 2_775 . ? O1 Gd1 O9 128.8(2) . . ? O5 Gd1 O9 141.3(2) . . ? O3 Gd1 O9 78.81(19) . . ? O7 Gd1 O9 73.88(18) . . ? O10 Gd1 O9 55.36(18) . . ? N1 Gd1 O9 112.7(2) . . ? N2 Gd1 O9 126.0(2) . . ? O9 Gd1 S 93.38(15) 2_775 . ? O1 Gd1 S 100.77(17) . . ? O5 Gd1 S 164.10(15) . . ? O3 Gd1 S 92.56(14) . . ? O7 Gd1 S 68.08(13) . . ? O10 Gd1 S 27.44(13) . . ? N1 Gd1 S 97.72(16) . . ? N2 Gd1 S 131.22(16) . . ? O9 Gd1 S 28.57(13) . . ? O15 Gd2 O11 154.0(2) . . ? O15 Gd2 O6 75.8(2) . 1_455 ? O11 Gd2 O6 78.5(2) . 1_455 ? O15 Gd2 O13 84.0(3) . . ? O11 Gd2 O13 90.1(2) . . ? O6 Gd2 O13 68.7(2) 1_455 . ? O15 Gd2 O14 90.8(2) . . ? O11 Gd2 O14 78.4(2) . . ? O6 Gd2 O14 73.7(2) 1_455 . ? O13 Gd2 O14 142.1(2) . . ? O15 Gd2 O8 78.1(2) . . ? O11 Gd2 O8 124.0(2) . . ? O6 Gd2 O8 134.3(2) 1_455 . ? O13 Gd2 O8 71.8(2) . . ? O14 Gd2 O8 143.5(2) . . ? O15 Gd2 O3 118.2(2) . 2_775 ? O11 Gd2 O3 81.0(2) . 2_775 ? O6 Gd2 O3 142.1(2) 1_455 2_775 ? O13 Gd2 O3 142.8(2) . 2_775 ? O14 Gd2 O3 71.3(2) . 2_775 ? O8 Gd2 O3 83.5(2) . 2_775 ? O15 Gd2 O7 129.1(2) . . ? O11 Gd2 O7 72.25(19) . . ? O6 Gd2 O7 131.3(2) 1_455 . ? O13 Gd2 O7 73.3(2) . . ? O14 Gd2 O7 133.9(2) . . ? O8 Gd2 O7 51.88(18) . . ? O3 Gd2 O7 69.57(18) 2_775 . ? O15 Gd2 O4 66.7(2) . 2_775 ? O11 Gd2 O4 129.4(2) . 2_775 ? O6 Gd2 O4 127.3(2) 1_455 2_775 ? O13 Gd2 O4 137.4(2) . 2_775 ? O14 Gd2 O4 71.4(2) . 2_775 ? O8 Gd2 O4 72.3(2) . 2_775 ? O3 Gd2 O4 51.48(19) 2_775 2_775 ? O7 Gd2 O4 101.2(2) . 2_775 ? O15 Gd2 C14 103.3(2) . . ? O11 Gd2 C14 98.7(2) . . ? O6 Gd2 C14 140.2(2) 1_455 . ? O13 Gd2 C14 71.6(2) . . ? O14 Gd2 C14 145.4(2) . . ? O8 Gd2 C14 25.4(2) . . ? O3 Gd2 C14 74.2(2) 2_775 . ? O7 Gd2 C14 26.5(2) . . ? O4 Gd2 C14 85.3(2) 2_775 . ? O15 Gd2 C7 91.7(2) . 2_775 ? O11 Gd2 C7 104.6(2) . 2_775 ? O6 Gd2 C7 136.5(2) 1_455 2_775 ? O13 Gd2 C7 152.4(2) . 2_775 ? O14 Gd2 C7 64.9(2) . 2_775 ? O8 Gd2 C7 80.7(2) . 2_775 ? O3 Gd2 C7 26.8(2) 2_775 2_775 ? O7 Gd2 C7 88.9(2) . 2_775 ? O4 Gd2 C7 25.4(2) 2_775 2_775 ? C14 Gd2 C7 83.1(2) . 2_775 ? O15 Gd2 H13A 80.7 . . ? O11 Gd2 H13A 85.6 . . ? O6 Gd2 H13A 49.9 1_455 . ? O13 Gd2 H13A 18.8 . . ? O14 Gd2 H13A 123.4 . . ? O8 Gd2 H13A 89.3 . . ? O3 Gd2 H13A 157.6 2_775 . ? O7 Gd2 H13A 89.3 . . ? O4 Gd2 H13A 145.0 2_775 . ? C14 Gd2 H13A 90.3 . . ? C7 Gd2 H13A 168.5 2_775 . ? O16 Cu O16 180.000(2) . 2_666 ? O16 Cu N3 82.9(3) . . ? O16 Cu N3 97.1(3) 2_666 . ? O16 Cu N3 97.1(3) . 2_666 ? O16 Cu N3 82.9(3) 2_666 2_666 ? N3 Cu N3 180.000(1) . 2_666 ? O12 S O10 113.8(4) . . ? O12 S O11 109.4(4) . . ? O10 S O11 110.8(4) . . ? O12 S O9 111.7(4) . . ? O10 S O9 103.0(3) . . ? O11 S O9 107.7(3) . . ? O12 S Gd1 139.1(3) . . ? O10 S Gd1 51.1(2) . . ? O11 S Gd1 111.4(2) . . ? O9 S Gd1 53.5(2) . . ? C6 O1 Gd1 125.9(6) . . ? C7 O3 Gd1 124.1(5) . . ? C7 O3 Gd2 91.9(5) . 2_775 ? Gd1 O3 Gd2 138.5(2) . 2_775 ? C7 O4 Gd2 91.8(5) . 2_775 ? C13 O5 Gd1 125.8(5) . . ? C13 O6 Gd2 163.8(6) . 1_655 ? C14 O7 Gd1 123.3(5) . . ? C14 O7 Gd2 91.7(5) . . ? Gd1 O7 Gd2 141.9(2) . . ? C14 O8 Gd2 95.3(5) . . ? S O9 Gd1 144.2(4) . 2_775 ? S O9 Gd1 98.0(3) . . ? Gd1 O9 Gd1 114.2(2) 2_775 . ? S O10 Gd1 101.5(3) . . ? S O11 Gd2 141.2(4) . . ? Gd2 O13 H13A 47.4 . . ? Gd2 O13 H13B 155.1 . . ? H13A O13 H13B 107.7 . . ? Gd2 O14 H14A 112.8 . . ? Gd2 O14 H14B 138.2 . . ? H14A O14 H14B 107.7 . . ? C20 O15 Gd2 136.5(7) . . ? C20 O16 Cu 114.8(6) . . ? H17B O17 H17C 107.7 . . ? C5 N1 C1 118.5(7) . . ? C5 N1 Gd1 122.1(5) . . ? C1 N1 Gd1 119.4(6) . . ? C8 N2 C12 118.1(7) . . ? C8 N2 Gd1 120.9(5) . . ? C12 N2 Gd1 120.8(5) . . ? C15 N3 C19 118.2(10) . . ? C15 N3 Cu 112.2(7) . . ? C19 N3 Cu 129.6(8) . . ? N1 C1 C2 122.2(9) . . ? N1 C1 C6 113.4(7) . . ? C2 C1 C6 124.4(8) . . ? C1 C2 C3 118.6(9) . . ? C1 C2 H2A 120.7 . . ? C3 C2 H2A 120.7 . . ? C4 C3 C2 119.9(9) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 118.5(9) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? N1 C5 C4 122.2(8) . . ? N1 C5 C7 113.6(7) . . ? C4 C5 C7 124.1(8) . . ? O2 C6 O1 126.9(9) . . ? O2 C6 C1 118.2(8) . . ? O1 C6 C1 114.7(8) . . ? O4 C7 O3 121.6(8) . . ? O4 C7 C5 121.7(8) . . ? O3 C7 C5 116.6(7) . . ? O4 C7 Gd2 62.8(4) . 2_775 ? O3 C7 Gd2 61.3(4) . 2_775 ? C5 C7 Gd2 160.7(6) . 2_775 ? N2 C8 C9 123.1(8) . . ? N2 C8 C13 113.2(7) . . ? C9 C8 C13 123.6(8) . . ? C10 C9 C8 117.3(8) . . ? C10 C9 H9A 121.4 . . ? C8 C9 H9A 121.4 . . ? C11 C10 C9 120.2(8) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? C12 C11 C10 119.0(9) . . ? C12 C11 H11A 120.5 . . ? C10 C11 H11A 120.5 . . ? N2 C12 C11 122.3(8) . . ? N2 C12 C14 113.6(7) . . ? C11 C12 C14 124.1(8) . . ? O6 C13 O5 125.1(8) . . ? O6 C13 C8 119.6(7) . . ? O5 C13 C8 115.3(7) . . ? O8 C14 O7 120.9(8) . . ? O8 C14 C12 121.6(7) . . ? O7 C14 C12 117.5(7) . . ? O8 C14 Gd2 59.3(4) . . ? O7 C14 Gd2 61.8(4) . . ? C12 C14 Gd2 175.7(6) . . ? N3 C15 C16 125.2(10) . . ? N3 C15 C20 113.5(9) . . ? C16 C15 C20 121.2(9) . . ? C15 C16 C17 115.5(11) . . ? C15 C16 H16A 122.3 . . ? C17 C16 H16A 122.3 . . ? C18 C17 C16 120.0(11) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C19 C18 C17 118.8(11) . . ? C19 C18 H18A 120.6 . . ? C17 C18 H18A 120.6 . . ? N3 C19 C18 122.3(11) . . ? N3 C19 H19A 118.8 . . ? C18 C19 H19A 118.8 . . ? O15 C20 O16 123.8(9) . . ? O15 C20 C15 120.5(9) . . ? O16 C20 C15 115.7(8) . . ? 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 O13 H13A O6 0.85 1.87 2.707(9) 168.9 1_455 O14 H14A O5 0.85 2.16 2.786(9) 130.7 2_775 O14 H14B O11 0.85 2.26 2.995(9) 144.7 2_675 O14 H14B O12 0.85 2.35 3.114(10) 150.1 2_675 O14 H14B S 0.85 2.81 3.655(7) 171.0 2_675 O17 H17B O16 0.85 1.95 2.788(10) 167.4 2_676 O17 H17C O1 0.85 1.97 2.751(10) 151.4 . O17 H17C O7 0.85 2.64 3.163(9) 120.6 . _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 5.856 _refine_diff_density_min -1.771 _refine_diff_density_rms 0.330 data_1_779196 _database_code_depnum_ccdc_archive 'CCDC 779196' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cu0.50 N3 O17 S Sm2' _chemical_formula_weight 934.89 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' 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.490(4) _cell_length_b 10.903(5) _cell_length_c 13.026(5) _cell_angle_alpha 88.736(14) _cell_angle_beta 66.916(7) _cell_angle_gamma 80.309(10) _cell_volume 1349.4(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3328 _cell_measurement_theta_min 2.1429 _cell_measurement_theta_max 27.4294 _exptl_crystal_description Prism _exptl_crystal_colour Light-blue _exptl_crystal_size_max 0.1300 _exptl_crystal_size_mid 0.1200 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 895 _exptl_absorpt_coefficient_mu 4.858 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.537 _exptl_absorpt_correction_T_max 0.615 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'SCXmini CCD' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10587 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0974 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.43 _reflns_number_total 5915 _reflns_number_gt 4809 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1103P)^2^+3.8679P] 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 SHELXL _refine_ls_extinction_coef 0.0084(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5915 _refine_ls_number_parameters 395 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0904 _refine_ls_R_factor_gt 0.0733 _refine_ls_wR_factor_ref 0.2239 _refine_ls_wR_factor_gt 0.1909 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _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 Sm1 Sm 0.98370(5) 0.61422(5) 0.13179(4) 0.0259(2) Uani 1 1 d . . . Sm2 Sm 0.60080(5) 0.40082(5) 0.18921(4) 0.0276(2) Uani 1 1 d . . . Cu Cu 0.5000 0.0000 0.5000 0.0441(6) Uani 1 2 d S . . S S 0.7524(3) 0.6593(3) 0.0316(2) 0.0281(6) Uani 1 1 d . . . O1 O 0.8584(9) 0.7248(7) 0.3098(6) 0.0349(18) Uani 1 1 d . . . O2 O 0.7587(10) 0.9020(9) 0.4173(8) 0.058(3) Uani 1 1 d . . . O3 O 1.1604(7) 0.6887(7) -0.0365(7) 0.0344(18) Uani 1 1 d . . . O4 O 1.2835(9) 0.8293(9) -0.1287(8) 0.048(2) Uani 1 1 d . . . O5 O 1.2023(8) 0.5985(8) 0.1614(7) 0.0372(19) Uani 1 1 d . . . O6 O 1.3649(8) 0.4979(8) 0.2197(7) 0.042(2) Uani 1 1 d . . . O7 O 0.7975(8) 0.4842(7) 0.2215(6) 0.0316(17) Uani 1 1 d . . . O8 O 0.7213(8) 0.3250(8) 0.3188(7) 0.044(2) Uani 1 1 d . . . O9 O 0.8918(7) 0.5720(8) -0.0164(7) 0.0319(17) Uani 1 1 d . . . O10 O 0.7680(9) 0.7348(8) 0.1165(7) 0.0373(19) Uani 1 1 d . . . O11 O 0.6422(7) 0.5829(8) 0.0868(7) 0.039(2) Uani 1 1 d . . . O12 O 0.7219(9) 0.7293(8) -0.0531(7) 0.043(2) Uani 1 1 d . . . O13 O 0.4901(9) 0.5290(9) 0.3635(8) 0.046(2) Uani 1 1 d . . . H13A H 0.4867 0.5358 0.2994 0.056 Uiso 1 1 d R . . H13B H 0.4173 0.5751 0.4099 0.056 Uiso 1 1 d R . . O14 O 0.5649(9) 0.3451(9) 0.0204(7) 0.045(2) Uani 1 1 d . . . H14A H 0.6423 0.3141 -0.0320 0.054 Uiso 1 1 d R . . H14B H 0.4990 0.3380 -0.0005 0.054 Uiso 1 1 d R . . O15 O 0.4613(8) 0.2563(8) 0.2927(7) 0.0399(19) Uani 1 1 d . . . O16 O 0.5161(10) 0.1535(9) 0.4221(7) 0.047(2) Uani 1 1 d . . . O17 O 0.6390(9) 0.6217(8) 0.4617(7) 0.044(2) Uani 1 1 d . . . H17B H 0.6016 0.6952 0.4894 0.053 Uiso 1 1 d R . . H17C H 0.7146 0.6261 0.4056 0.053 Uiso 1 1 d R . . N1 N 1.0160(9) 0.8376(8) 0.1419(7) 0.0270(18) Uani 1 1 d . . . N2 N 1.0188(9) 0.4573(9) 0.2745(8) 0.030(2) Uani 1 1 d . . . N3 N 0.4560(11) -0.0520(10) 0.3712(9) 0.046(3) Uani 1 1 d . . . C1 C 0.9374(13) 0.9099(12) 0.2347(10) 0.041(3) Uani 1 1 d . . . C2 C 0.9421(15) 1.0369(12) 0.2450(12) 0.046(3) Uani 1 1 d . . . H2A H 0.8808 1.0857 0.3083 0.056 Uiso 1 1 calc R . . C3 C 1.0415(14) 1.0865(12) 0.1574(12) 0.047(3) Uani 1 1 d . . . H3A H 1.0534 1.1681 0.1640 0.056 Uiso 1 1 calc R . . C4 C 1.1265(13) 1.0125(12) 0.0561(11) 0.044(3) Uani 1 1 d . . . H4A H 1.1898 1.0454 -0.0056 0.052 Uiso 1 1 calc R . . C5 C 1.1086(11) 0.8867(9) 0.0554(9) 0.027(2) Uani 1 1 d . . . C6 C 0.8405(12) 0.8422(12) 0.3304(10) 0.038(3) Uani 1 1 d . . . C7 C 1.1899(11) 0.8005(12) -0.0441(10) 0.035(3) Uani 1 1 d . . . C8 C 1.1311(11) 0.4522(11) 0.2996(9) 0.032(2) Uani 1 1 d . . . C9 C 1.1494(12) 0.3800(14) 0.3838(11) 0.044(3) Uani 1 1 d . . . H9A H 1.2296 0.3743 0.3991 0.053 Uiso 1 1 calc R . . C10 C 1.0385(13) 0.3156(13) 0.4450(12) 0.047(3) Uani 1 1 d . . . H10A H 1.0421 0.2710 0.5057 0.056 Uiso 1 1 calc R . . C11 C 0.9270(13) 0.3179(12) 0.4164(10) 0.041(3) Uani 1 1 d . . . H11A H 0.8576 0.2706 0.4529 0.049 Uiso 1 1 calc R . . C12 C 0.9202(11) 0.3919(11) 0.3324(8) 0.028(2) Uani 1 1 d . . . C13 C 1.2411(11) 0.5245(11) 0.2222(9) 0.032(2) Uani 1 1 d . . . C14 C 0.8065(11) 0.3970(11) 0.2893(9) 0.030(2) Uani 1 1 d . . . C15 C 0.4521(14) 0.0400(16) 0.3033(12) 0.052(4) Uani 1 1 d . . . C16 C 0.4202(17) 0.0317(15) 0.2121(12) 0.057(4) Uani 1 1 d . . . H16A H 0.4160 0.0987 0.1674 0.069 Uiso 1 1 calc R . . C17 C 0.394(2) -0.0866(15) 0.1902(15) 0.070(5) Uani 1 1 d . . . H17A H 0.3724 -0.0988 0.1287 0.084 Uiso 1 1 calc R . . C18 C 0.3993(18) -0.1840(14) 0.2597(15) 0.064(4) Uani 1 1 d . . . H18A H 0.3835 -0.2617 0.2444 0.077 Uiso 1 1 calc R . . C19 C 0.4285(16) -0.1640(13) 0.3513(12) 0.051(3) Uani 1 1 d . . . H19A H 0.4294 -0.2277 0.3998 0.061 Uiso 1 1 calc R . . C20 C 0.4785(13) 0.1630(13) 0.3403(10) 0.040(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 Sm1 0.0231(3) 0.0259(4) 0.0306(3) 0.0049(2) -0.0114(2) -0.0078(2) Sm2 0.0229(3) 0.0297(4) 0.0322(4) 0.0070(2) -0.0117(2) -0.0081(2) Cu 0.0483(12) 0.0483(14) 0.0374(12) 0.0036(10) -0.0136(10) -0.0212(11) S 0.0225(11) 0.0273(14) 0.0378(14) 0.0057(11) -0.0148(10) -0.0063(10) O1 0.047(5) 0.029(4) 0.031(4) 0.001(3) -0.015(3) -0.015(4) O2 0.055(6) 0.047(6) 0.049(6) -0.011(5) 0.004(5) -0.010(5) O3 0.023(3) 0.032(4) 0.042(5) -0.003(3) -0.006(3) -0.007(3) O4 0.038(5) 0.041(5) 0.057(6) 0.015(4) -0.010(4) -0.012(4) O5 0.027(4) 0.038(5) 0.051(5) 0.013(4) -0.019(4) -0.008(3) O6 0.022(4) 0.048(5) 0.060(6) 0.015(4) -0.019(4) -0.009(4) O7 0.028(4) 0.033(4) 0.035(4) 0.007(3) -0.013(3) -0.009(3) O8 0.039(4) 0.047(5) 0.062(6) 0.032(4) -0.029(4) -0.029(4) O9 0.020(3) 0.035(4) 0.043(4) 0.001(4) -0.015(3) -0.004(3) O10 0.044(5) 0.034(5) 0.037(4) -0.006(4) -0.019(4) -0.002(4) O11 0.024(4) 0.039(5) 0.063(5) 0.027(4) -0.023(4) -0.015(3) O12 0.046(5) 0.051(6) 0.041(5) 0.022(4) -0.028(4) -0.011(4) O13 0.040(5) 0.057(6) 0.045(5) -0.008(4) -0.019(4) -0.008(4) O14 0.038(5) 0.060(6) 0.048(5) 0.010(5) -0.025(4) -0.015(4) O15 0.031(4) 0.031(5) 0.051(5) 0.007(4) -0.008(4) -0.011(4) O16 0.059(6) 0.037(5) 0.041(5) 0.000(4) -0.012(4) -0.017(4) O17 0.045(5) 0.039(5) 0.040(5) -0.008(4) -0.006(4) -0.013(4) N1 0.033(4) 0.021(5) 0.030(5) 0.001(4) -0.014(4) -0.009(4) N2 0.024(4) 0.032(5) 0.035(5) 0.004(4) -0.010(4) -0.012(4) N3 0.043(6) 0.043(6) 0.054(7) 0.023(5) -0.019(5) -0.016(5) C1 0.043(7) 0.039(7) 0.038(7) -0.003(5) -0.009(5) -0.013(6) C2 0.056(8) 0.026(6) 0.057(8) -0.002(6) -0.022(6) -0.005(6) C3 0.054(8) 0.024(6) 0.058(8) 0.007(6) -0.018(6) -0.008(6) C4 0.043(7) 0.034(7) 0.050(8) 0.014(6) -0.010(6) -0.016(6) C5 0.036(5) 0.017(5) 0.036(6) 0.010(4) -0.022(5) -0.011(4) C6 0.031(6) 0.042(7) 0.039(7) 0.004(5) -0.011(5) -0.004(5) C7 0.022(5) 0.039(7) 0.043(7) 0.015(5) -0.010(5) -0.009(5) C8 0.033(5) 0.032(6) 0.034(6) 0.002(5) -0.013(4) -0.016(5) C9 0.026(5) 0.061(9) 0.054(8) 0.013(7) -0.025(5) -0.010(6) C10 0.035(6) 0.050(8) 0.064(9) 0.034(7) -0.025(6) -0.022(6) C11 0.039(6) 0.048(8) 0.043(7) 0.016(6) -0.020(5) -0.020(6) C12 0.037(6) 0.033(6) 0.020(5) 0.002(4) -0.016(4) -0.009(5) C13 0.024(5) 0.041(7) 0.033(6) 0.001(5) -0.009(4) -0.014(5) C14 0.026(5) 0.038(7) 0.030(5) -0.001(5) -0.013(4) -0.011(5) C15 0.038(7) 0.069(10) 0.050(8) 0.015(7) -0.018(6) -0.014(7) C16 0.075(10) 0.051(9) 0.046(8) 0.002(7) -0.025(7) -0.009(8) C17 0.108(14) 0.049(10) 0.080(12) 0.000(8) -0.062(11) -0.020(10) C18 0.080(11) 0.033(8) 0.087(12) 0.004(8) -0.044(10) -0.001(8) C19 0.067(9) 0.036(7) 0.055(8) -0.007(6) -0.029(7) -0.011(7) C20 0.041(6) 0.045(8) 0.029(6) 0.011(5) -0.008(5) -0.008(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 Sm1 O1 2.399(8) . ? Sm1 O9 2.406(8) 2_765 ? Sm1 O5 2.448(7) . ? Sm1 O3 2.478(8) . ? Sm1 O10 2.495(8) . ? Sm1 O7 2.502(7) . ? Sm1 N1 2.527(8) . ? Sm1 O9 2.553(7) . ? Sm1 N2 2.589(9) . ? Sm1 S 3.144(3) . ? Sm2 O15 2.361(8) . ? Sm2 O11 2.372(8) . ? Sm2 O6 2.402(7) 1_455 ? Sm2 O13 2.446(9) . ? Sm2 O14 2.477(8) . ? Sm2 O8 2.528(8) . ? Sm2 O3 2.558(7) 2_765 ? Sm2 O7 2.567(7) . ? Sm2 O4 2.589(9) 2_765 ? Sm2 C7 2.918(12) 2_765 ? Sm2 C14 2.920(10) . ? Sm2 H13A 1.9525 . ? Cu O16 1.935(9) 2_656 ? Cu O16 1.935(9) . ? Cu N3 2.022(12) 2_656 ? Cu N3 2.022(12) . ? S O12 1.436(8) . ? S O10 1.469(8) . ? S O11 1.481(7) . ? S O9 1.509(8) . ? O1 C6 1.281(15) . ? O2 C6 1.236(14) . ? O3 C7 1.299(14) . ? O3 Sm2 2.558(7) 2_765 ? O4 C7 1.232(13) . ? O4 Sm2 2.589(9) 2_765 ? O5 C13 1.248(14) . ? O6 C13 1.270(12) . ? O6 Sm2 2.402(7) 1_655 ? O7 C14 1.300(14) . ? O8 C14 1.231(13) . ? O9 Sm1 2.406(8) 2_765 ? O13 H13A 0.8500 . ? O13 H13B 0.8501 . ? O14 H14A 0.8500 . ? O14 H14B 0.8500 . ? O15 C20 1.205(15) . ? O16 C20 1.270(15) . ? O17 H17B 0.8500 . ? O17 H17C 0.8499 . ? N1 C5 1.338(13) . ? N1 C1 1.343(15) . ? N2 C12 1.327(13) . ? N2 C8 1.333(13) . ? N3 C15 1.328(18) . ? N3 C19 1.353(17) . ? C1 C2 1.405(17) . ? C1 C6 1.533(17) . ? C2 C3 1.382(19) . ? C2 H2A 0.9300 . ? C3 C4 1.439(19) . ? C3 H3A 0.9300 . ? C4 C5 1.416(16) . ? C4 H4A 0.9300 . ? C5 C7 1.486(17) . ? C7 Sm2 2.918(12) 2_765 ? C8 C9 1.392(17) . ? C8 C13 1.525(14) . ? C9 C10 1.416(17) . ? C9 H9A 0.9300 . ? C10 C11 1.356(16) . ? C10 H10A 0.9300 . ? C11 C12 1.362(15) . ? C11 H11A 0.9300 . ? C12 C14 1.498(14) . ? C15 C16 1.36(2) . ? C15 C20 1.54(2) . ? C16 C17 1.42(2) . ? C16 H16A 0.9300 . ? C17 C18 1.39(2) . ? C17 H17A 0.9300 . ? C18 C19 1.37(2) . ? C18 H18A 0.9300 . ? C19 H19A 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 O1 Sm1 O9 152.4(3) . 2_765 ? O1 Sm1 O5 89.4(3) . . ? O9 Sm1 O5 82.4(3) 2_765 . ? O1 Sm1 O3 126.6(3) . . ? O9 Sm1 O3 75.7(3) 2_765 . ? O5 Sm1 O3 72.2(3) . . ? O1 Sm1 O10 75.9(3) . . ? O9 Sm1 O10 120.7(2) 2_765 . ? O5 Sm1 O10 152.6(3) . . ? O3 Sm1 O10 98.0(3) . . ? O1 Sm1 O7 79.8(3) . . ? O9 Sm1 O7 83.6(3) 2_765 . ? O5 Sm1 O7 125.3(3) . . ? O3 Sm1 O7 151.0(3) . . ? O10 Sm1 O7 75.3(3) . . ? O1 Sm1 N1 63.6(3) . . ? O9 Sm1 N1 137.7(3) 2_765 . ? O5 Sm1 N1 75.7(3) . . ? O3 Sm1 N1 63.3(3) . . ? O10 Sm1 N1 77.1(3) . . ? O7 Sm1 N1 138.4(3) . . ? O1 Sm1 O9 128.5(3) . . ? O9 Sm1 O9 66.1(3) 2_765 . ? O5 Sm1 O9 141.7(3) . . ? O3 Sm1 O9 79.0(2) . . ? O10 Sm1 O9 55.0(2) . . ? O7 Sm1 O9 74.1(2) . . ? N1 Sm1 O9 113.1(3) . . ? O1 Sm1 N2 75.5(3) . . ? O9 Sm1 N2 77.3(3) 2_765 . ? O5 Sm1 N2 62.9(3) . . ? O3 Sm1 N2 129.9(3) . . ? O10 Sm1 N2 132.2(3) . . ? O7 Sm1 N2 62.4(3) . . ? N1 Sm1 N2 121.1(3) . . ? O9 Sm1 N2 125.5(3) . . ? O1 Sm1 S 100.6(2) . . ? O9 Sm1 S 93.52(18) 2_765 . ? O5 Sm1 S 164.6(2) . . ? O3 Sm1 S 92.39(19) . . ? O10 Sm1 S 27.21(18) . . ? O7 Sm1 S 68.56(18) . . ? N1 Sm1 S 98.2(2) . . ? O9 Sm1 S 28.35(17) . . ? N2 Sm1 S 130.80(19) . . ? O15 Sm2 O11 154.7(3) . . ? O15 Sm2 O6 76.1(3) . 1_455 ? O11 Sm2 O6 78.9(3) . 1_455 ? O15 Sm2 O13 84.4(3) . . ? O11 Sm2 O13 89.9(3) . . ? O6 Sm2 O13 68.6(3) 1_455 . ? O15 Sm2 O14 90.8(3) . . ? O11 Sm2 O14 78.8(3) . . ? O6 Sm2 O14 74.2(3) 1_455 . ? O13 Sm2 O14 142.5(3) . . ? O15 Sm2 O8 78.3(3) . . ? O11 Sm2 O8 122.9(3) . . ? O6 Sm2 O8 133.4(3) 1_455 . ? O13 Sm2 O8 70.8(3) . . ? O14 Sm2 O8 144.3(3) . . ? O15 Sm2 O3 116.9(3) . 2_765 ? O11 Sm2 O3 81.8(3) . 2_765 ? O6 Sm2 O3 143.0(3) 1_455 2_765 ? O13 Sm2 O3 142.8(3) . 2_765 ? O14 Sm2 O3 71.2(3) . 2_765 ? O8 Sm2 O3 83.5(3) . 2_765 ? O15 Sm2 O7 128.7(3) . . ? O11 Sm2 O7 72.0(2) . . ? O6 Sm2 O7 131.2(3) 1_455 . ? O13 Sm2 O7 72.9(3) . . ? O14 Sm2 O7 134.0(3) . . ? O8 Sm2 O7 51.1(2) . . ? O3 Sm2 O7 70.0(2) 2_765 . ? O15 Sm2 O4 66.3(3) . 2_765 ? O11 Sm2 O4 129.5(3) . 2_765 ? O6 Sm2 O4 127.6(3) 1_455 2_765 ? O13 Sm2 O4 137.1(3) . 2_765 ? O14 Sm2 O4 71.5(3) . 2_765 ? O8 Sm2 O4 73.1(3) . 2_765 ? O3 Sm2 O4 50.6(3) 2_765 2_765 ? O7 Sm2 O4 101.0(3) . 2_765 ? O15 Sm2 C7 90.8(3) . 2_765 ? O11 Sm2 C7 105.0(3) . 2_765 ? O6 Sm2 C7 136.6(3) 1_455 2_765 ? O13 Sm2 C7 152.2(3) . 2_765 ? O14 Sm2 C7 64.7(3) . 2_765 ? O8 Sm2 C7 81.5(3) . 2_765 ? O3 Sm2 C7 26.4(3) 2_765 2_765 ? O7 Sm2 C7 89.3(3) . 2_765 ? O4 Sm2 C7 24.9(3) 2_765 2_765 ? O15 Sm2 C14 103.0(3) . . ? O11 Sm2 C14 98.4(3) . . ? O6 Sm2 C14 139.9(3) 1_455 . ? O13 Sm2 C14 71.4(3) . . ? O14 Sm2 C14 145.2(3) . . ? O8 Sm2 C14 24.8(3) . . ? O3 Sm2 C14 74.0(3) 2_765 . ? O7 Sm2 C14 26.4(3) . . ? O4 Sm2 C14 85.0(3) 2_765 . ? C7 Sm2 C14 83.2(3) 2_765 . ? O15 Sm2 H13A 91.7 . . ? O11 Sm2 H13A 76.5 . . ? O6 Sm2 H13A 54.4 1_455 . ? O13 Sm2 H13A 18.2 . . ? O14 Sm2 H13A 126.0 . . ? O8 Sm2 H13A 88.6 . . ? O3 Sm2 H13A 147.8 2_765 . ? O7 Sm2 H13A 80.7 . . ? O4 Sm2 H13A 153.5 2_765 . ? C7 Sm2 H13A 169.0 2_765 . ? C14 Sm2 H13A 85.8 . . ? O16 Cu O16 180.0(6) 2_656 . ? O16 Cu N3 81.9(4) 2_656 2_656 ? O16 Cu N3 98.1(4) . 2_656 ? O16 Cu N3 98.1(4) 2_656 . ? O16 Cu N3 81.9(4) . . ? N3 Cu N3 180.000(1) 2_656 . ? O12 S O10 114.7(5) . . ? O12 S O11 109.8(5) . . ? O10 S O11 109.5(5) . . ? O12 S O9 111.9(5) . . ? O10 S O9 103.0(5) . . ? O11 S O9 107.6(5) . . ? O12 S Sm1 139.5(4) . . ? O10 S Sm1 51.0(3) . . ? O11 S Sm1 110.6(3) . . ? O9 S Sm1 53.5(3) . . ? C6 O1 Sm1 127.1(7) . . ? C7 O3 Sm1 124.1(7) . . ? C7 O3 Sm2 92.5(6) . 2_765 ? Sm1 O3 Sm2 137.4(3) . 2_765 ? C7 O4 Sm2 92.7(8) . 2_765 ? C13 O5 Sm1 126.5(7) . . ? C13 O6 Sm2 165.4(8) . 1_655 ? C14 O7 Sm1 123.6(6) . . ? C14 O7 Sm2 92.1(6) . . ? Sm1 O7 Sm2 140.9(3) . . ? C14 O8 Sm2 95.7(7) . . ? S O9 Sm1 144.4(4) . 2_765 ? S O9 Sm1 98.2(4) . . ? Sm1 O9 Sm1 113.9(3) 2_765 . ? S O10 Sm1 101.8(4) . . ? S O11 Sm2 142.3(4) . . ? Sm2 O13 H13A 45.9 . . ? Sm2 O13 H13B 148.4 . . ? H13A O13 H13B 107.7 . . ? Sm2 O14 H14A 111.2 . . ? Sm2 O14 H14B 140.4 . . ? H14A O14 H14B 107.7 . . ? C20 O15 Sm2 136.6(8) . . ? C20 O16 Cu 117.2(8) . . ? H17B O17 H17C 107.7 . . ? C5 N1 C1 118.8(10) . . ? C5 N1 Sm1 121.3(7) . . ? C1 N1 Sm1 119.9(7) . . ? C12 N2 C8 118.9(10) . . ? C12 N2 Sm1 121.5(7) . . ? C8 N2 Sm1 119.2(7) . . ? C15 N3 C19 120.2(13) . . ? C15 N3 Cu 112.3(10) . . ? C19 N3 Cu 127.5(9) . . ? N1 C1 C2 123.7(12) . . ? N1 C1 C6 114.3(11) . . ? C2 C1 C6 122.0(11) . . ? C3 C2 C1 117.4(12) . . ? C3 C2 H2A 121.3 . . ? C1 C2 H2A 121.3 . . ? C2 C3 C4 120.4(12) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 116.3(11) . . ? C5 C4 H4A 121.8 . . ? C3 C4 H4A 121.8 . . ? N1 C5 C4 123.1(11) . . ? N1 C5 C7 115.2(9) . . ? C4 C5 C7 121.7(10) . . ? O2 C6 O1 127.2(12) . . ? O2 C6 C1 119.3(12) . . ? O1 C6 C1 113.5(10) . . ? O4 C7 O3 120.5(12) . . ? O4 C7 C5 123.3(11) . . ? O3 C7 C5 116.1(9) . . ? O4 C7 Sm2 62.4(7) . 2_765 ? O3 C7 Sm2 61.1(6) . 2_765 ? C5 C7 Sm2 160.1(8) . 2_765 ? N2 C8 C9 122.4(10) . . ? N2 C8 C13 113.8(10) . . ? C9 C8 C13 123.6(10) . . ? C8 C9 C10 116.0(10) . . ? C8 C9 H9A 122.0 . . ? C10 C9 H9A 122.0 . . ? C11 C10 C9 121.1(11) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 117.6(11) . . ? C10 C11 H11A 121.2 . . ? C12 C11 H11A 121.2 . . ? N2 C12 C11 123.8(10) . . ? N2 C12 C14 113.4(9) . . ? C11 C12 C14 122.5(10) . . ? O5 C13 O6 126.1(10) . . ? O5 C13 C8 116.1(9) . . ? O6 C13 C8 117.6(10) . . ? O8 C14 O7 120.6(10) . . ? O8 C14 C12 122.2(11) . . ? O7 C14 C12 117.2(9) . . ? O8 C14 Sm2 59.5(6) . . ? O7 C14 Sm2 61.5(5) . . ? C12 C14 Sm2 175.8(7) . . ? N3 C15 C16 124.6(15) . . ? N3 C15 C20 113.9(12) . . ? C16 C15 C20 121.4(14) . . ? C15 C16 C17 115.3(15) . . ? C15 C16 H16A 122.4 . . ? C17 C16 H16A 122.4 . . ? C18 C17 C16 120.6(14) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C19 C18 C17 119.1(15) . . ? C19 C18 H18A 120.5 . . ? C17 C18 H18A 120.5 . . ? N3 C19 C18 120.2(14) . . ? N3 C19 H19A 119.9 . . ? C18 C19 H19A 119.9 . . ? O15 C20 O16 126.6(13) . . ? O15 C20 C15 119.6(12) . . ? O16 C20 C15 113.8(11) . . ? 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 O13 H13A O6 0.85 2.03 2.731(12) 139.2 1_455 O14 H14A O5 0.85 2.17 2.803(12) 131.2 2_765 O14 H14B O11 0.85 2.24 3.006(11) 149.2 2_665 O14 H14B O12 0.85 2.38 3.113(12) 144.3 2_665 O14 H14B S 0.85 2.82 3.655(9) 169.1 2_665 O17 H17B O16 0.85 1.96 2.800(12) 167.3 2_666 O17 H17C O1 0.85 2.00 2.771(11) 150.4 . O17 H17C O7 0.85 2.64 3.176(11) 122.1 . _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 5.263 _refine_diff_density_min -2.460 _refine_diff_density_rms 0.486