# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Parthasarathi Dastidar' _publ_contact_author_email parthod123@rediffmail.com _publ_section_title ; Metalla-macro-tricyclic Cryptands: Anion Encapsulation and Selective Separation of Sulfate via in situ Crystallization ; _publ_author_name 'Parthasarathi Dastidar' #END data_3 _database_code_depnum_ccdc_archive 'CCDC 739005' #TrackingRef '- CIFS_FINAL.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C72 H60 Cl4 Cu2 N16 O22' _chemical_formula_weight 1770.24 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I4/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z' 'y, -x, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' 'y+1/2, -x+1/2, z+1/2' '-x, -y, -z' 'x, y, -z' 'y, -x, -z' '-y, x, -z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 15.7237(8) _cell_length_b 15.7237(8) _cell_length_c 14.9552(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3697.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'truncated octahedron' _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1812 _exptl_absorpt_coefficient_mu 0.810 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9091 _exptl_absorpt_correction_T_max 0.9234 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX CCD diffractomter' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16240 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2351 _reflns_number_gt 1896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX' _computing_cell_refinement 'Bruker SMART APEX' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'MERCURY 2.3' _computing_publication_material SHELXL-97 _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^)+(0.0848P)^2^+21.6277P] 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 2351 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.1743 _refine_ls_wR_factor_gt 0.1639 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 Cu1 Cu 0.5000 0.5000 0.80731(6) 0.0158(3) Uani 1 4 d S . . Cl1 Cl 0.5000 0.5000 1.0000 0.0181(5) Uani 1 8 d S . . N1 N 0.42850(18) 0.60714(18) 0.8068(2) 0.0169(6) Uani 1 1 d . . . N2 N 0.4043(2) 0.79897(19) 0.6726(2) 0.0186(6) Uani 1 1 d . . . O1 O 0.3486(2) 0.91958(17) 0.73366(18) 0.0296(7) Uani 1 1 d . . . C1 C 0.4396(2) 0.6684(2) 0.7454(2) 0.0177(7) Uani 1 1 d . . . O2 O 0.5000 0.5000 0.6416(4) 0.0332(14) Uani 1 4 d S . . C2 C 0.3922(2) 0.7432(2) 0.7444(2) 0.0164(7) Uani 1 1 d . . . C3 C 0.3328(2) 0.7564(2) 0.8119(2) 0.0211(7) Uani 1 1 d . . . C4 C 0.3218(2) 0.6922(2) 0.8750(2) 0.0224(8) Uani 1 1 d . . . C5 C 0.3692(2) 0.6186(2) 0.8705(2) 0.0205(7) Uani 1 1 d . . . C6 C 0.3783(2) 0.8825(2) 0.6694(2) 0.0198(7) Uani 1 1 d . . . C7 C 0.3874(2) 0.9251(2) 0.5808(2) 0.0186(7) Uani 1 1 d . . . C8 C 0.3846(3) 0.8812(3) 0.5000 0.0188(10) Uani 1 2 d S . . C9 C 0.3932(3) 1.0135(2) 0.5806(3) 0.0236(8) Uani 1 1 d . . . C10 C 0.3967(4) 1.0571(3) 0.5000 0.0270(12) Uani 1 2 d S . . Cl2 Cl 0.59401(10) 0.68864(10) 0.5000 0.0194(4) Uani 0.75 2 d SP . . O3 O 0.6805(5) 0.7113(7) 0.5000 0.077(3) Uani 0.75 2 d SP . . O4 O 0.5869(7) 0.6008(6) 0.5000 0.124(5) Uani 0.75 2 d SP . . O5 O 0.5584(5) 0.7276(5) 0.5769(5) 0.093(3) Uani 0.75 1 d P . . H1 H 0.479(2) 0.657(2) 0.702(3) 0.009(9) Uiso 1 1 d . . . H2 H 0.300(3) 0.806(3) 0.815(3) 0.014(10) Uiso 1 1 d . . . H3 H 0.280(3) 0.699(3) 0.919(3) 0.023(11) Uiso 1 1 d . . . H9 H 0.397(3) 1.042(3) 0.638(3) 0.033(12) Uiso 1 1 d . . . H4 H 0.363(3) 0.576(3) 0.903(3) 0.021(11) Uiso 1 1 d . . . H8 H 0.372(5) 0.819(5) 0.5000 0.04(2) Uiso 1 2 d S . . H10 H 0.407(4) 1.114(5) 0.5000 0.036(19) Uiso 1 2 d S . . H1N H 0.431(3) 0.786(3) 0.632(4) 0.025(12) Uiso 1 1 d . . . H2O H 0.525(10) 0.533(8) 0.601(6) 0.04(3) Uiso 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0143(3) 0.0143(3) 0.0188(4) 0.000 0.000 0.000 Cl1 0.0192(7) 0.0192(7) 0.0158(11) 0.000 0.000 0.000 N1 0.0160(13) 0.0185(14) 0.0162(14) 0.0012(11) -0.0011(11) -0.0009(11) N2 0.0218(15) 0.0201(15) 0.0139(14) 0.0001(11) 0.0039(12) 0.0054(12) O1 0.0495(18) 0.0212(13) 0.0182(14) -0.0038(11) 0.0016(13) 0.0079(13) C1 0.0189(17) 0.0174(16) 0.0167(16) -0.0013(13) 0.0019(13) 0.0015(13) O2 0.039(2) 0.039(2) 0.021(3) 0.000 0.000 0.000 C2 0.0178(16) 0.0162(16) 0.0152(16) -0.0009(13) -0.0021(13) -0.0009(13) C3 0.0212(17) 0.0231(17) 0.0189(17) -0.0001(14) 0.0006(14) 0.0073(14) C4 0.0217(17) 0.0304(19) 0.0151(17) 0.0007(15) 0.0022(14) 0.0055(15) C5 0.0234(18) 0.0232(18) 0.0148(16) 0.0043(14) 0.0005(14) 0.0000(14) C6 0.0241(18) 0.0187(16) 0.0166(16) -0.0018(13) -0.0038(14) 0.0014(14) C7 0.0187(16) 0.0171(16) 0.0200(18) 0.0006(13) -0.0002(13) 0.0021(13) C8 0.023(2) 0.015(2) 0.019(2) 0.000 0.000 0.0001(19) C9 0.029(2) 0.0172(17) 0.0242(19) -0.0039(14) -0.0031(15) 0.0020(14) C10 0.041(3) 0.014(2) 0.026(3) 0.000 0.000 0.004(2) Cl2 0.0184(7) 0.0141(7) 0.0257(8) 0.000 0.000 -0.0023(6) O3 0.045(4) 0.102(7) 0.085(7) 0.000 0.000 -0.029(5) O4 0.092(8) 0.036(5) 0.243(17) 0.000 0.000 -0.002(5) O5 0.120(6) 0.078(4) 0.081(5) 0.006(4) 0.060(4) 0.018(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 Cu1 N1 2.025(3) 4_565 ? Cu1 N1 2.025(3) 2_665 ? Cu1 N1 2.025(3) . ? Cu1 N1 2.025(3) 3_655 ? N1 C1 1.342(4) . ? N1 C5 1.345(5) . ? N2 C6 1.377(5) . ? N2 C2 1.400(5) . ? N2 H1N 0.76(5) . ? O1 C6 1.217(5) . ? C1 C2 1.392(5) . ? C1 H1 0.91(4) . ? O2 H2O 0.88(8) . ? C2 C3 1.392(5) . ? C3 C4 1.393(5) . ? C3 H2 0.93(4) . ? C4 C5 1.377(5) . ? C4 H3 0.93(4) . ? C5 H4 0.83(5) . ? C6 C7 1.493(5) . ? C7 C8 1.392(4) . ? C7 C9 1.393(5) . ? C8 C7 1.392(4) 10_556 ? C8 H8 0.99(8) . ? C9 C10 1.387(5) . ? C9 H9 0.97(5) . ? C10 C9 1.387(5) 10_556 ? C10 H10 0.90(7) . ? Cl2 O4 1.385(9) 1 ? Cl2 O4 1.385(9) . ? Cl2 O3 1.406(8) . ? Cl2 O5 1.418(6) . ? Cl2 O5 1.418(6) 1 ? Cl2 O5 1.418(6) 10_556 ? O4 O4 0.00(2) 1 ? O5 O5 0.000(15) 1 ? 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 N1 Cu1 N1 90.001(1) 4_565 2_665 ? N1 Cu1 N1 89.998(2) 4_565 . ? N1 Cu1 N1 179.60(17) 2_665 . ? N1 Cu1 N1 179.60(17) 4_565 3_655 ? N1 Cu1 N1 89.999(1) 2_665 3_655 ? N1 Cu1 N1 90.000(2) . 3_655 ? C1 N1 C5 118.6(3) . . ? C1 N1 Cu1 121.8(2) . . ? C5 N1 Cu1 119.6(2) . . ? C6 N2 C2 125.7(3) . . ? C6 N2 H1N 113(4) . . ? C2 N2 H1N 121(4) . . ? N1 C1 C2 122.9(3) . . ? N1 C1 H1 116(2) . . ? C2 C1 H1 121(2) . . ? C3 C2 C1 118.5(3) . . ? C3 C2 N2 123.6(3) . . ? C1 C2 N2 117.7(3) . . ? C2 C3 C4 117.8(3) . . ? C2 C3 H2 122(2) . . ? C4 C3 H2 120(2) . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H3 121(3) . . ? C3 C4 H3 118(3) . . ? N1 C5 C4 121.5(3) . . ? N1 C5 H4 113(3) . . ? C4 C5 H4 125(3) . . ? O1 C6 N2 123.0(3) . . ? O1 C6 C7 121.5(3) . . ? N2 C6 C7 115.5(3) . . ? C8 C7 C9 119.7(4) . . ? C8 C7 C6 123.0(3) . . ? C9 C7 C6 117.1(3) . . ? C7 C8 C7 120.4(5) 10_556 . ? C7 C8 H8 119.5(4) 10_556 . ? C7 C8 H8 119.5(4) . . ? C10 C9 C7 119.8(4) . . ? C10 C9 H9 122(3) . . ? C7 C9 H9 118(3) . . ? C9 C10 C9 120.6(5) 10_556 . ? C9 C10 H10 119.6(4) 10_556 . ? C9 C10 H10 119.6(4) . . ? O4 Cl2 O4 0.0(10) 1 . ? O4 Cl2 O3 109.3(7) 1 . ? O4 Cl2 O3 109.3(7) . . ? O4 Cl2 O5 113.5(4) 1 . ? O4 Cl2 O5 113.5(4) . . ? O3 Cl2 O5 105.8(4) . . ? O4 Cl2 O5 113.5(4) 1 1 ? O4 Cl2 O5 113.5(4) . 1 ? O3 Cl2 O5 105.8(4) . 1 ? O5 Cl2 O5 0.0(6) . 1 ? O4 Cl2 O5 113.5(4) 1 10_556 ? O4 Cl2 O5 113.5(4) . 10_556 ? O3 Cl2 O5 105.8(4) . 10_556 ? O5 Cl2 O5 108.4(7) . 10_556 ? O5 Cl2 O5 108.4(7) 1 10_556 ? O4 O4 Cl2 0(10) 1 . ? O5 O5 Cl2 0(10) 1 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 N1 C1 53.2(3) 4_565 . . . ? N1 Cu1 N1 C1 -36.5(4) 2_665 . . . ? N1 Cu1 N1 C1 -126.4(2) 3_655 . . . ? N1 Cu1 N1 C5 -125.5(2) 4_565 . . . ? N1 Cu1 N1 C5 144.7(3) 2_665 . . . ? N1 Cu1 N1 C5 54.9(3) 3_655 . . . ? C5 N1 C1 C2 -0.3(5) . . . . ? Cu1 N1 C1 C2 -179.0(3) . . . . ? N1 C1 C2 C3 2.4(5) . . . . ? N1 C1 C2 N2 -174.5(3) . . . . ? C6 N2 C2 C3 18.4(6) . . . . ? C6 N2 C2 C1 -164.9(3) . . . . ? C1 C2 C3 C4 -2.5(5) . . . . ? N2 C2 C3 C4 174.2(3) . . . . ? C2 C3 C4 C5 0.7(6) . . . . ? C1 N1 C5 C4 -1.7(5) . . . . ? Cu1 N1 C5 C4 177.1(3) . . . . ? C3 C4 C5 N1 1.5(6) . . . . ? C2 N2 C6 O1 7.3(6) . . . . ? C2 N2 C6 C7 -171.5(3) . . . . ? O1 C6 C7 C8 -151.0(4) . . . . ? N2 C6 C7 C8 27.8(5) . . . . ? O1 C6 C7 C9 24.6(5) . . . . ? N2 C6 C7 C9 -156.5(3) . . . . ? C9 C7 C8 C7 -0.1(7) . . . 10_556 ? C6 C7 C8 C7 175.4(3) . . . 10_556 ? C8 C7 C9 C10 -0.5(6) . . . . ? C6 C7 C9 C10 -176.3(4) . . . . ? C7 C9 C10 C9 1.0(9) . . . 10_556 ? O3 Cl2 O4 O4 0.0 . . . 1 ? O5 Cl2 O4 O4 0.00(19) . . . 1 ? O5 Cl2 O4 O4 0.00(19) 1 . . 1 ? O5 Cl2 O4 O4 0.00(19) 10_556 . . 1 ? O4 Cl2 O5 O5 0.0(10) 1 . . 1 ? O4 Cl2 O5 O5 0.0(10) . . . 1 ? O3 Cl2 O5 O5 0.0(12) . . . 1 ? O5 Cl2 O5 O5 0.0(12) 10_556 . . 1 ? 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 N2 H1N O5 0.76(5) 2.36(5) 3.030(7) 148(5) 1 O2 H2O O4 0.88(8) 2.10(9) 2.978(8) 175(15) 1 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.660 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.129 # Attachment '- CIFS_FINAL.CIF' data_1a _database_code_depnum_ccdc_archive 'CCDC 739006' #TrackingRef '- CIFS_FINAL.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C72 H92 Cu2 N16 O34 S2' _chemical_formula_weight 1916.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.874(3) _cell_length_b 13.211(3) _cell_length_c 14.871(4) _cell_angle_alpha 103.703(3) _cell_angle_beta 99.287(3) _cell_angle_gamma 112.473(3) _cell_volume 2179.4(9) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 998 _exptl_absorpt_coefficient_mu 0.630 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8335 _exptl_absorpt_correction_T_max 0.9632 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12647 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 20.00 _reflns_number_total 4062 _reflns_number_gt 3285 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER APEX II' _computing_cell_refinement 'BRUKER APEX II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'MERCURY 2.3, ORTEP3V2' _computing_publication_material SHELXTL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogen atoms attached with O49 and O50 were restrained using DFIX commands and O-H distances were restricted to 0.8 angstrom with e.s.d. of 0.01. ; _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^)+(0.0816P)^2^+1.5684P] 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 4062 _refine_ls_number_parameters 539 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.998 _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 Cu1 Cu 0.58298(5) 0.82831(5) 0.74907(4) 0.0271(3) Uani 1 1 d . . . S S 0.27902(11) 0.01060(11) 0.86062(9) 0.0264(4) Uani 1 1 d . . . N1 N 0.5907(4) 0.9570(3) 0.6941(3) 0.0272(11) Uani 1 1 d . . . C2 C 0.6743(5) 0.9990(4) 0.6515(4) 0.0296(14) Uani 1 1 d . . . H2 H 0.7294 0.9698 0.6486 0.035 Uiso 1 1 calc R . . C3 C 0.6802(5) 1.0851(5) 0.6117(4) 0.0340(14) Uani 1 1 d . . . H3 H 0.7390 1.1130 0.5825 0.041 Uiso 1 1 calc R . . C4 C 0.5992(5) 1.1298(5) 0.6150(4) 0.0311(14) Uani 1 1 d . . . H4 H 0.6026 1.1875 0.5883 0.037 Uiso 1 1 calc R . . C5 C 0.5131(5) 1.0864(4) 0.6590(4) 0.0264(13) Uani 1 1 d . . . C6 C 0.5122(4) 0.9996(4) 0.6972(3) 0.0244(13) Uani 1 1 d . . . H6 H 0.4539 0.9699 0.7263 0.029 Uiso 1 1 calc R . . N7 N 0.4295(4) 1.1276(4) 0.6724(3) 0.0285(11) Uani 1 1 d . . . H7 H 0.3905 1.1054 0.7116 0.034 Uiso 1 1 calc R . . C8 C 0.4033(5) 1.1986(5) 0.6305(4) 0.0297(14) Uani 1 1 d . . . O9 O 0.4417(3) 1.2219(3) 0.5630(3) 0.0342(9) Uani 1 1 d . . . C10 C 0.3370(4) 1.2555(4) 0.6744(4) 0.0239(13) Uani 1 1 d . . . C11 C 0.2684(5) 1.2909(5) 0.6188(4) 0.0315(14) Uani 1 1 d . . . H11 H 0.2557 1.2686 0.5523 0.038 Uiso 1 1 calc R . . C12 C 0.2198(5) 1.3582(5) 0.6612(4) 0.0356(15) Uani 1 1 d . . . H12 H 0.1709 1.3778 0.6231 0.043 Uiso 1 1 calc R . . C13 C 0.2426(5) 1.3971(5) 0.7602(4) 0.0352(15) Uani 1 1 d . . . H13 H 0.2131 1.4467 0.7888 0.042 Uiso 1 1 calc R . . C14 C 0.3088(4) 1.3627(4) 0.8163(4) 0.0247(13) Uani 1 1 d . . . C15 C 0.3548(4) 1.2899(4) 0.7743(4) 0.0235(13) Uani 1 1 d . . . H15 H 0.3972 1.2643 0.8124 0.028 Uiso 1 1 calc R . . C16 C 0.3410(4) 1.4150(5) 0.9239(4) 0.0260(13) Uani 1 1 d . . . O17 O 0.3613(3) 1.5178(3) 0.9603(2) 0.0324(9) Uani 1 1 d . . . N18 N 0.3490(3) 1.3450(3) 0.9747(3) 0.0241(11) Uani 1 1 d . . . H18 H 0.3358 1.2761 0.9420 0.029 Uiso 1 1 calc R . . C19 C 0.3764(4) 1.3724(4) 1.0745(4) 0.0235(13) Uani 1 1 d . . . C20 C 0.3857(4) 1.4728(5) 1.1393(4) 0.0288(14) Uani 1 1 d . . . H20 H 0.3723 1.5285 1.1178 0.035 Uiso 1 1 calc R . . C21 C 0.4154(4) 1.4873(5) 1.2365(4) 0.0321(14) Uani 1 1 d . . . H21 H 0.4232 1.5542 1.2811 0.039 Uiso 1 1 calc R . . C22 C 0.4336(4) 1.4046(5) 1.2682(4) 0.0310(14) Uani 1 1 d . . . H22 H 0.4557 1.4176 1.3341 0.037 Uiso 1 1 calc R . . N23 N 0.4202(3) 1.3045(4) 1.2062(3) 0.0276(11) Uani 1 1 d . . . C24 C 0.3920(4) 1.2910(4) 1.1118(4) 0.0258(13) Uani 1 1 d . . . H24 H 0.3822 1.2222 1.0685 0.031 Uiso 1 1 calc R . . N25 N 0.4103(3) 0.7373(3) 0.6778(3) 0.0249(11) Uani 1 1 d . . . C26 C 0.3712(5) 0.7222(4) 0.5846(4) 0.0310(14) Uani 1 1 d . . . H26 H 0.4252 0.7483 0.5508 0.037 Uiso 1 1 calc R . . C27 C 0.2543(5) 0.6694(5) 0.5371(4) 0.0364(15) Uani 1 1 d . . . H27 H 0.2302 0.6615 0.4724 0.044 Uiso 1 1 calc R . . C28 C 0.1721(5) 0.6278(5) 0.5846(4) 0.0333(14) Uani 1 1 d . . . H28 H 0.0924 0.5922 0.5532 0.040 Uiso 1 1 calc R . . C29 C 0.2127(5) 0.6410(4) 0.6809(4) 0.0285(14) Uani 1 1 d . . . C30 C 0.3322(4) 0.6971(4) 0.7247(4) 0.0250(13) Uani 1 1 d . . . H30 H 0.3591 0.7070 0.7896 0.030 Uiso 1 1 calc R . . N31 N 0.1372(4) 0.6035(3) 0.7378(3) 0.0272(11) Uani 1 1 d . . . H31 H 0.1601 0.6441 0.7979 0.033 Uiso 1 1 calc R . . C32 C 0.0300(4) 0.5076(5) 0.7055(4) 0.0292(14) Uani 1 1 d . . . O33 O -0.0080(3) 0.4394(3) 0.6238(3) 0.0305(9) Uani 1 1 d . . . C34 C -0.0320(4) 0.4956(4) 0.7818(4) 0.0248(13) Uani 1 1 d . . . C35 C -0.1050(4) 0.3860(5) 0.7812(4) 0.0315(14) Uani 1 1 d . . . H35 H -0.1171 0.3205 0.7323 0.038 Uiso 1 1 calc R . . C36 C -0.1606(5) 0.3742(5) 0.8546(4) 0.0406(16) Uani 1 1 d . . . H36 H -0.2107 0.3010 0.8537 0.049 Uiso 1 1 calc R . . C37 C -0.1401(5) 0.4726(5) 0.9287(4) 0.0355(15) Uani 1 1 d . . . H37 H -0.1753 0.4650 0.9783 0.043 Uiso 1 1 calc R . . C38 C -0.0680(4) 0.5813(5) 0.9290(4) 0.0293(14) Uani 1 1 d . . . C39 C -0.0179(4) 0.5913(4) 0.8531(4) 0.0249(13) Uani 1 1 d . . . H39 H 0.0261 0.6647 0.8508 0.030 Uiso 1 1 calc R . . C40 C -0.0435(5) 0.6868(5) 1.0103(4) 0.0344(15) Uani 1 1 d . . . O41 O -0.1063(3) 0.6872(3) 1.0628(3) 0.0421(10) Uani 1 1 d . . . N42 N 0.0557(4) 0.7824(4) 1.0195(3) 0.0332(12) Uani 1 1 d . . . H42 H 0.1019 0.7721 0.9863 0.040 Uiso 1 1 calc R . . C43 C 0.0881(5) 0.8953(5) 1.0783(4) 0.0282(14) Uani 1 1 d . . . C44 C 0.0083(5) 0.9398(5) 1.0916(4) 0.0353(15) Uani 1 1 d . . . H44 H -0.0716 0.8932 1.0643 0.042 Uiso 1 1 calc R . . C45 C 0.0498(5) 1.0555(5) 1.1463(4) 0.0382(15) Uani 1 1 d . . . H45 H -0.0019 1.0879 1.1555 0.046 Uiso 1 1 calc R . . C46 C 0.1694(5) 1.1220(5) 1.1871(4) 0.0308(14) Uani 1 1 d . . . H46 H 0.1969 1.1995 1.2235 0.037 Uiso 1 1 calc R . . N47 N 0.2462(4) 1.0785(4) 1.1759(3) 0.0251(11) Uani 1 1 d . . . C48 C 0.2060(5) 0.9673(5) 1.1225(4) 0.0289(14) Uani 1 1 d . . . H48 H 0.2596 0.9370 1.1146 0.035 Uiso 1 1 calc R . . O49 O 0.5313(3) 0.9180(3) 0.8860(3) 0.0308(9) Uani 1 1 d D . . O50 O 0.6367(4) 0.7441(3) 0.6069(3) 0.0334(9) Uani 1 1 d D . . O51 O 0.2502(3) 0.1045(3) 0.9007(2) 0.0336(9) Uani 1 1 d . . . O52 O 0.2417(3) 0.7537(3) 0.9385(2) 0.0349(9) Uani 1 1 d . . . O53 O 0.2778(3) -0.0011(3) 0.7588(3) 0.0491(11) Uani 1 1 d . . . O54 O 0.4171(3) 1.7486(3) 1.0654(3) 0.0438(10) Uani 1 1 d . . . O55 O 0.4005(3) 0.0409(4) 0.9150(3) 0.0523(11) Uani 1 1 d . . . O56 O 0.1974(3) -0.0976(3) 0.8649(3) 0.0540(12) Uani 1 1 d . . . H49A H 0.559(5) 0.924(5) 0.9402(16) 0.04(2) Uiso 1 1 d D . . H49B H 0.486(3) 0.945(4) 0.882(4) 0.026(18) Uiso 1 1 d D . . H50A H 0.692(3) 0.731(5) 0.602(4) 0.05(2) Uiso 1 1 d D . . H50B H 0.611(4) 0.745(4) 0.5545(17) 0.032(18) Uiso 1 1 d 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 Cu1 0.0187(4) 0.0262(4) 0.0240(4) 0.0041(3) -0.0025(3) 0.0030(3) S 0.0180(8) 0.0288(9) 0.0235(8) 0.0042(7) 0.0017(6) 0.0055(7) N1 0.016(3) 0.028(3) 0.021(3) -0.003(2) -0.002(2) 0.002(2) C2 0.021(3) 0.030(4) 0.025(3) 0.001(3) 0.000(3) 0.005(3) C3 0.031(4) 0.038(4) 0.036(4) 0.013(3) 0.017(3) 0.015(3) C4 0.034(4) 0.028(3) 0.026(3) 0.008(3) 0.006(3) 0.010(3) C5 0.023(3) 0.025(3) 0.020(3) -0.001(3) 0.001(3) 0.006(3) C6 0.017(3) 0.031(3) 0.015(3) 0.002(3) 0.003(2) 0.004(3) N7 0.031(3) 0.032(3) 0.024(3) 0.013(2) 0.014(2) 0.012(2) C8 0.031(3) 0.028(3) 0.019(3) 0.006(3) -0.002(3) 0.006(3) O9 0.039(2) 0.041(2) 0.024(2) 0.013(2) 0.0091(19) 0.018(2) C10 0.017(3) 0.022(3) 0.027(4) 0.005(3) 0.004(3) 0.006(3) C11 0.027(3) 0.038(4) 0.022(3) 0.006(3) 0.000(3) 0.012(3) C12 0.030(3) 0.045(4) 0.033(4) 0.015(3) 0.003(3) 0.020(3) C13 0.036(4) 0.034(4) 0.029(4) 0.004(3) 0.008(3) 0.012(3) C14 0.020(3) 0.023(3) 0.023(3) 0.006(3) 0.001(3) 0.003(3) C15 0.018(3) 0.020(3) 0.023(4) 0.005(3) 0.002(3) 0.001(3) C16 0.016(3) 0.030(4) 0.029(4) 0.007(3) 0.005(3) 0.008(3) O17 0.030(2) 0.029(3) 0.030(2) 0.006(2) 0.0055(18) 0.0077(19) N18 0.025(3) 0.018(2) 0.022(3) 0.002(2) 0.001(2) 0.006(2) C19 0.014(3) 0.023(3) 0.021(4) 0.002(3) 0.000(2) 0.001(3) C20 0.025(3) 0.028(4) 0.031(4) 0.013(3) 0.006(3) 0.008(3) C21 0.034(4) 0.027(3) 0.029(4) 0.002(3) 0.007(3) 0.011(3) C22 0.025(3) 0.035(4) 0.014(3) 0.001(3) -0.001(2) 0.000(3) N23 0.017(3) 0.029(3) 0.018(3) 0.000(2) -0.001(2) -0.002(2) C24 0.018(3) 0.024(3) 0.024(4) 0.001(3) 0.002(3) 0.003(3) N25 0.022(3) 0.025(3) 0.016(3) 0.003(2) -0.005(2) 0.004(2) C26 0.022(4) 0.032(3) 0.026(4) 0.002(3) 0.002(3) 0.004(3) C27 0.030(4) 0.036(4) 0.025(3) 0.009(3) -0.002(3) 0.001(3) C28 0.018(3) 0.038(4) 0.025(4) 0.004(3) -0.007(3) 0.001(3) C29 0.022(4) 0.026(3) 0.026(4) 0.004(3) 0.003(3) 0.004(3) C30 0.022(4) 0.025(3) 0.016(3) 0.002(3) -0.001(3) 0.004(3) N31 0.023(3) 0.026(3) 0.022(2) 0.002(2) 0.004(2) 0.005(2) C32 0.014(3) 0.024(3) 0.039(4) 0.009(3) -0.001(3) 0.001(3) O33 0.024(2) 0.024(2) 0.020(2) -0.006(2) -0.0061(18) -0.0007(18) C34 0.015(3) 0.020(3) 0.027(3) 0.004(3) -0.003(3) 0.001(3) C35 0.020(3) 0.033(4) 0.031(3) 0.003(3) 0.005(3) 0.006(3) C36 0.027(4) 0.039(4) 0.045(4) 0.012(4) 0.002(3) 0.009(3) C37 0.024(3) 0.040(4) 0.029(3) 0.007(3) 0.002(3) 0.005(3) C38 0.020(3) 0.028(4) 0.029(4) 0.006(3) 0.002(3) 0.004(3) C39 0.007(3) 0.023(3) 0.030(3) 0.005(3) -0.003(3) -0.002(2) C40 0.023(4) 0.040(4) 0.035(4) 0.008(3) 0.002(3) 0.013(3) O41 0.032(2) 0.045(3) 0.045(3) 0.009(2) 0.020(2) 0.012(2) N42 0.019(3) 0.027(3) 0.031(3) -0.010(2) 0.007(2) 0.000(3) C43 0.021(4) 0.031(4) 0.022(3) 0.000(3) 0.005(3) 0.006(3) C44 0.019(3) 0.043(4) 0.024(3) -0.003(3) 0.000(3) 0.003(3) C45 0.028(4) 0.045(4) 0.031(4) -0.002(3) 0.001(3) 0.016(3) C46 0.028(4) 0.037(4) 0.018(3) 0.001(3) 0.001(3) 0.011(3) N47 0.020(3) 0.025(3) 0.017(2) -0.003(2) -0.003(2) 0.005(2) C48 0.022(4) 0.040(4) 0.020(3) 0.007(3) 0.007(3) 0.010(3) O49 0.024(2) 0.037(2) 0.025(3) 0.005(2) 0.000(2) 0.013(2) O50 0.035(3) 0.045(3) 0.018(2) 0.009(2) 0.004(2) 0.017(2) O51 0.024(2) 0.025(2) 0.042(2) -0.0001(18) 0.0049(18) 0.0080(18) O52 0.024(2) 0.034(2) 0.029(2) 0.0017(18) 0.0043(17) 0.0018(18) O53 0.054(3) 0.052(3) 0.032(2) 0.007(2) 0.013(2) 0.017(2) O54 0.037(2) 0.042(2) 0.037(2) 0.0049(19) 0.0028(19) 0.008(2) O55 0.034(3) 0.068(3) 0.043(2) 0.000(2) -0.004(2) 0.027(2) O56 0.046(3) 0.033(3) 0.082(3) 0.018(2) 0.030(2) 0.011(2) _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 Cu1 N23 2.008(4) 2_677 ? Cu1 N47 2.021(4) 2_677 ? Cu1 N25 2.025(4) . ? Cu1 N1 2.031(4) . ? Cu1 O49 2.427(4) . ? S O56 1.438(4) . ? S O51 1.451(4) . ? S O53 1.482(4) . ? S O55 1.490(4) . ? N1 C6 1.333(6) . ? N1 C2 1.342(6) . ? C2 C3 1.384(7) . ? C2 H2 0.9300 . ? C3 C4 1.382(7) . ? C3 H3 0.9300 . ? C4 C5 1.383(7) . ? C4 H4 0.9300 . ? C5 C6 1.391(7) . ? C5 N7 1.400(6) . ? C6 H6 0.9300 . ? N7 C8 1.354(6) . ? N7 H7 0.8600 . ? C8 O9 1.239(6) . ? C8 C10 1.469(7) . ? C10 C11 1.395(7) . ? C10 C15 1.398(7) . ? C11 C12 1.366(7) . ? C11 H11 0.9300 . ? C12 C13 1.380(7) . ? C12 H12 0.9300 . ? C13 C14 1.370(7) . ? C13 H13 0.9300 . ? C14 C15 1.391(7) . ? C14 C16 1.501(7) . ? C15 H15 0.9300 . ? C16 O17 1.242(6) . ? C16 N18 1.346(6) . ? N18 C19 1.392(6) . ? N18 H18 0.8600 . ? C19 C24 1.385(7) . ? C19 C20 1.392(7) . ? C20 C21 1.380(7) . ? C20 H20 0.9300 . ? C21 C22 1.369(7) . ? C21 H21 0.9300 . ? C22 N23 1.350(6) . ? C22 H22 0.9300 . ? N23 C24 1.342(6) . ? N23 Cu1 2.008(4) 2_677 ? C24 H24 0.9300 . ? N25 C30 1.332(6) . ? N25 C26 1.335(6) . ? C26 C27 1.368(7) . ? C26 H26 0.9300 . ? C27 C28 1.379(7) . ? C27 H27 0.9300 . ? C28 C29 1.388(7) . ? C28 H28 0.9300 . ? C29 C30 1.385(7) . ? C29 N31 1.416(6) . ? C30 H30 0.9300 . ? N31 C32 1.379(6) . ? N31 H31 0.8600 . ? C32 O33 1.216(6) . ? C32 C34 1.493(7) . ? C34 C39 1.373(7) . ? C34 C35 1.390(7) . ? C35 C36 1.405(7) . ? C35 H35 0.9300 . ? C36 C37 1.394(8) . ? C36 H36 0.9300 . ? C37 C38 1.379(7) . ? C37 H37 0.9300 . ? C38 C39 1.395(7) . ? C38 C40 1.499(8) . ? C39 H39 0.9300 . ? C40 O41 1.212(6) . ? C40 N42 1.368(7) . ? N42 C43 1.398(7) . ? N42 H42 0.8600 . ? C43 C44 1.382(7) . ? C43 C48 1.385(7) . ? C44 C45 1.389(7) . ? C44 H44 0.9300 . ? C45 C46 1.386(7) . ? C45 H45 0.9300 . ? C46 N47 1.333(6) . ? C46 H46 0.9300 . ? N47 C48 1.338(6) . ? N47 Cu1 2.021(4) 2_677 ? C48 H48 0.9300 . ? O49 H49A 0.801(11) . ? O49 H49B 0.798(11) . ? O50 H50A 0.803(11) . ? O50 H50B 0.801(11) . ? O52 O52 0.000(12) 1 ? 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 N23 Cu1 N47 89.60(17) 2_677 2_677 ? N23 Cu1 N25 90.48(16) 2_677 . ? N47 Cu1 N25 178.08(17) 2_677 . ? N23 Cu1 N1 175.04(18) 2_677 . ? N47 Cu1 N1 90.22(17) 2_677 . ? N25 Cu1 N1 89.86(16) . . ? N23 Cu1 O49 94.48(16) 2_677 . ? N47 Cu1 O49 89.13(15) 2_677 . ? N25 Cu1 O49 88.95(15) . . ? N1 Cu1 O49 90.47(16) . . ? O56 S O51 111.4(2) . . ? O56 S O53 109.1(2) . . ? O51 S O53 109.7(2) . . ? O56 S O55 110.8(2) . . ? O51 S O55 108.5(2) . . ? O53 S O55 107.3(2) . . ? C6 N1 C2 118.5(5) . . ? C6 N1 Cu1 121.4(4) . . ? C2 N1 Cu1 120.0(4) . . ? N1 C2 C3 121.2(5) . . ? N1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 120.4(5) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 118.3(5) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C4 C5 C6 118.2(5) . . ? C4 C5 N7 124.6(5) . . ? C6 C5 N7 117.1(5) . . ? N1 C6 C5 123.3(5) . . ? N1 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? C8 N7 C5 127.1(5) . . ? C8 N7 H7 116.4 . . ? C5 N7 H7 116.4 . . ? O9 C8 N7 121.3(5) . . ? O9 C8 C10 121.4(5) . . ? N7 C8 C10 117.1(5) . . ? C11 C10 C15 118.8(5) . . ? C11 C10 C8 120.0(5) . . ? C15 C10 C8 120.5(5) . . ? C12 C11 C10 120.5(5) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.5(5) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 120.0(5) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.4(5) . . ? C13 C14 C16 118.5(5) . . ? C15 C14 C16 120.7(5) . . ? C14 C15 C10 119.6(5) . . ? C14 C15 H15 120.2 . . ? C10 C15 H15 120.2 . . ? O17 C16 N18 124.4(5) . . ? O17 C16 C14 119.6(5) . . ? N18 C16 C14 115.9(5) . . ? C16 N18 C19 126.9(4) . . ? C16 N18 H18 116.5 . . ? C19 N18 H18 116.5 . . ? C24 C19 N18 116.9(5) . . ? C24 C19 C20 117.5(5) . . ? N18 C19 C20 125.5(5) . . ? C21 C20 C19 118.1(5) . . ? C21 C20 H20 120.9 . . ? C19 C20 H20 120.9 . . ? C22 C21 C20 120.9(5) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? N23 C22 C21 121.8(5) . . ? N23 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C24 N23 C22 117.1(5) . . ? C24 N23 Cu1 120.7(4) . 2_677 ? C22 N23 Cu1 121.5(4) . 2_677 ? N23 C24 C19 124.4(5) . . ? N23 C24 H24 117.8 . . ? C19 C24 H24 117.8 . . ? C30 N25 C26 118.3(4) . . ? C30 N25 Cu1 120.4(3) . . ? C26 N25 Cu1 121.2(4) . . ? N25 C26 C27 122.1(5) . . ? N25 C26 H26 118.9 . . ? C27 C26 H26 118.9 . . ? C26 C27 C28 120.4(5) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C29 117.6(5) . . ? C27 C28 H28 121.2 . . ? C29 C28 H28 121.2 . . ? C30 C29 C28 118.8(5) . . ? C30 C29 N31 118.2(5) . . ? C28 C29 N31 123.0(5) . . ? N25 C30 C29 122.8(5) . . ? N25 C30 H30 118.6 . . ? C29 C30 H30 118.6 . . ? C32 N31 C29 125.8(4) . . ? C32 N31 H31 117.1 . . ? C29 N31 H31 117.1 . . ? O33 C32 N31 123.0(5) . . ? O33 C32 C34 124.2(5) . . ? N31 C32 C34 112.8(5) . . ? C39 C34 C35 119.1(5) . . ? C39 C34 C32 121.1(5) . . ? C35 C34 C32 119.8(5) . . ? C34 C35 C36 120.0(5) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C37 C36 C35 119.6(5) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C38 C37 C36 120.2(5) . . ? C38 C37 H37 119.9 . . ? C36 C37 H37 119.9 . . ? C37 C38 C39 119.1(5) . . ? C37 C38 C40 120.1(5) . . ? C39 C38 C40 120.7(5) . . ? C34 C39 C38 121.7(5) . . ? C34 C39 H39 119.2 . . ? C38 C39 H39 119.2 . . ? O41 C40 N42 123.2(5) . . ? O41 C40 C38 122.8(5) . . ? N42 C40 C38 114.0(5) . . ? C40 N42 C43 125.3(5) . . ? C40 N42 H42 117.3 . . ? C43 N42 H42 117.3 . . ? C44 C43 C48 118.5(5) . . ? C44 C43 N42 123.0(5) . . ? C48 C43 N42 118.4(5) . . ? C43 C44 C45 118.7(5) . . ? C43 C44 H44 120.6 . . ? C45 C44 H44 120.6 . . ? C46 C45 C44 119.1(5) . . ? C46 C45 H45 120.4 . . ? C44 C45 H45 120.4 . . ? N47 C46 C45 122.2(5) . . ? N47 C46 H46 118.9 . . ? C45 C46 H46 118.9 . . ? C46 N47 C48 118.6(4) . . ? C46 N47 Cu1 120.8(4) . 2_677 ? C48 N47 Cu1 120.2(4) . 2_677 ? N47 C48 C43 122.9(5) . . ? N47 C48 H48 118.6 . . ? C43 C48 H48 118.6 . . ? Cu1 O49 H49A 123(4) . . ? Cu1 O49 H49B 124(4) . . ? H49A O49 H49B 113(6) . . ? H50A O50 H50B 104(6) . . ? 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 N7 H7 O53 0.86 1.95 2.768(6) 157.6 1_565 N18 H18 O51 0.86 1.99 2.780(5) 153.1 1_565 N31 H31 O52 0.86 2.07 2.918(5) 170.7 1 N42 H42 O52 0.86 2.11 2.955(5) 165.8 1 O49 H49A O55 0.801(11) 2.025(19) 2.803(6) 164(6) 2_667 O49 H49B O55 0.798(11) 2.00(2) 2.765(6) 162(5) 1_565 O50 H50B O9 0.801(11) 1.976(15) 2.768(5) 170(5) 2_676 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 20.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.740 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.062 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.498 1.498 0.500 411.5 95.6 _platon_squeeze_details ; ? ; #END data_2 _database_code_depnum_ccdc_archive 'CCDC 739007' #TrackingRef '- CIFS_FINAL.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C74 H88 Cu2 F12 N16 O22 Si2' _chemical_formula_weight 1964.86 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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' _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 13.089(5) _cell_length_b 13.512(5) _cell_length_c 14.983(9) _cell_angle_alpha 105.233(12) _cell_angle_beta 97.716(12) _cell_angle_gamma 113.793(8) _cell_volume 2251.1(17) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1014 _exptl_absorpt_coefficient_mu 0.601 _exptl_absorpt_correction_type 'MULTI SCAN' _exptl_absorpt_correction_T_min 0.8791 _exptl_absorpt_correction_T_max 0.9535 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14018 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_sigmaI/netI 0.0720 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 20.58 _reflns_number_total 4545 _reflns_number_gt 3339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER APEX II' _computing_cell_refinement 'BRUKER APEX II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'MERCURY 2.3, ORTEP3V2' _computing_publication_material 'BRUKER SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogen atoms attached with O49 and O50 were restrained using DFIX commands and O-H distances were restricted to 0.8 angstrom with e.s.d. of 0.01. ; _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^)+(0.0837P)^2^+4.3105P] 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 4545 _refine_ls_number_parameters 594 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.057 _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 Cu1 Cu 0.58363(7) 0.82943(7) 0.73338(6) 0.0245(3) Uani 1 1 d . . . Si1 Si 0.27247(16) -0.01062(16) 0.85209(13) 0.0245(5) Uani 1 1 d . . . F1 F 0.2242(4) -0.0025(4) 0.7473(3) 0.0578(13) Uani 1 1 d . . . F2 F 0.3151(3) -0.1066(3) 0.7968(3) 0.0432(11) Uani 1 1 d . . . F3 F 0.3304(4) -0.0153(3) 0.9579(3) 0.0499(12) Uani 1 1 d . . . F4 F 0.1469(3) -0.1172(3) 0.8427(3) 0.0389(11) Uani 1 1 d . . . F5 F 0.2384(3) 0.0895(3) 0.9106(3) 0.0493(12) Uani 1 1 d . . . F6 F 0.4042(3) 0.0975(3) 0.8616(3) 0.0358(10) Uani 1 1 d . . . N1 N 0.5869(5) 0.9540(4) 0.6789(4) 0.0225(14) Uani 1 1 d . . . C2 C 0.6670(6) 0.9981(6) 0.6345(5) 0.0255(17) Uani 1 1 d . . . H2 H 0.7195 0.9686 0.6260 0.031 Uiso 1 1 calc R . . C3 C 0.6743(6) 1.0853(6) 0.6010(5) 0.0294(18) Uani 1 1 d . . . H3 H 0.7303 1.1130 0.5694 0.035 Uiso 1 1 calc R . . C4 C 0.5990(6) 1.1318(6) 0.6142(5) 0.0289(18) Uani 1 1 d . . . H4 H 0.6042 1.1917 0.5925 0.035 Uiso 1 1 calc R . . C5 C 0.5156(6) 1.0882(6) 0.6601(5) 0.0246(17) Uani 1 1 d . . . C6 C 0.5113(6) 0.9975(6) 0.6900(5) 0.0271(18) Uani 1 1 d . . . H6 H 0.4537 0.9656 0.7189 0.032 Uiso 1 1 calc R . . N7 N 0.4381(5) 1.1320(5) 0.6824(4) 0.0319(15) Uani 1 1 d . . . H7 H 0.4047 1.1138 0.7255 0.038 Uiso 1 1 calc R . . C8 C 0.4104(6) 1.2005(6) 0.6425(5) 0.0293(18) Uani 1 1 d . . . O9 O 0.4409(4) 1.2196(4) 0.5724(3) 0.0346(13) Uani 1 1 d . . . C10 C 0.3442(6) 1.2556(6) 0.6912(5) 0.0283(18) Uani 1 1 d . . . C11 C 0.2794(6) 1.2909(6) 0.6386(5) 0.0346(19) Uani 1 1 d . . . H11 H 0.2678 1.2693 0.5723 0.041 Uiso 1 1 calc R . . C12 C 0.2318(7) 1.3581(7) 0.6838(5) 0.039(2) Uani 1 1 d . . . H12 H 0.1862 1.3793 0.6476 0.047 Uiso 1 1 calc R . . C13 C 0.2517(6) 1.3934(6) 0.7820(5) 0.0318(19) Uani 1 1 d . . . H13 H 0.2231 1.4419 0.8124 0.038 Uiso 1 1 calc R . . C14 C 0.3146(6) 1.3568(6) 0.8361(5) 0.0282(18) Uani 1 1 d . . . C15 C 0.3602(6) 1.2877(6) 0.7904(5) 0.0280(18) Uani 1 1 d . . . H15 H 0.4017 1.2626 0.8261 0.034 Uiso 1 1 calc R . . C16 C 0.3443(6) 1.4066(6) 0.9439(5) 0.0283(18) Uani 1 1 d . . . O17 O 0.3709(4) 1.5089(4) 0.9848(3) 0.0360(13) Uani 1 1 d . . . N18 N 0.3428(5) 1.3334(5) 0.9908(4) 0.0293(15) Uani 1 1 d . . . H18 H 0.3225 1.2633 0.9559 0.035 Uiso 1 1 calc R . . C19 C 0.3713(6) 1.3606(6) 1.0909(5) 0.0261(17) Uani 1 1 d . . . C20 C 0.3868(6) 1.4634(6) 1.1579(5) 0.036(2) Uani 1 1 d . . . H20 H 0.3755 1.5185 1.1376 0.043 Uiso 1 1 calc R . . C21 C 0.4191(6) 1.4814(6) 1.2548(5) 0.0335(19) Uani 1 1 d . . . H21 H 0.4305 1.5493 1.3005 0.040 Uiso 1 1 calc R . . C22 C 0.4341(6) 1.3984(6) 1.2830(5) 0.0303(18) Uani 1 1 d . . . H22 H 0.4587 1.4125 1.3482 0.036 Uiso 1 1 calc R . . N23 N 0.4146(4) 1.2976(5) 1.2196(4) 0.0230(14) Uani 1 1 d . . . C24 C 0.3842(6) 1.2800(6) 1.1265(5) 0.0246(17) Uani 1 1 d . . . H24 H 0.3709 1.2100 1.0827 0.029 Uiso 1 1 calc R . . N25 N 0.4135(4) 0.7295(4) 0.6629(4) 0.0214(14) Uani 1 1 d . . . C26 C 0.3715(6) 0.7127(6) 0.5707(5) 0.0316(19) Uani 1 1 d . . . H26 H 0.4233 0.7400 0.5358 0.038 Uiso 1 1 calc R . . C27 C 0.2553(6) 0.6569(6) 0.5262(5) 0.039(2) Uani 1 1 d . . . H27 H 0.2297 0.6460 0.4618 0.047 Uiso 1 1 calc R . . C28 C 0.1754(6) 0.6166(6) 0.5761(5) 0.036(2) Uani 1 1 d . . . H28 H 0.0960 0.5816 0.5475 0.043 Uiso 1 1 calc R . . C29 C 0.2189(6) 0.6306(6) 0.6704(5) 0.0253(17) Uani 1 1 d . . . C30 C 0.3371(6) 0.6862(5) 0.7111(5) 0.0244(17) Uani 1 1 d . . . H30 H 0.3650 0.6941 0.7743 0.029 Uiso 1 1 calc R . . N31 N 0.1451(5) 0.5968(5) 0.7302(4) 0.0299(15) Uani 1 1 d . . . H31 H 0.1695 0.6400 0.7898 0.036 Uiso 1 1 calc R . . C32 C 0.0390(6) 0.5018(6) 0.7011(5) 0.0271(18) Uani 1 1 d . . . O33 O -0.0014(4) 0.4320(4) 0.6189(3) 0.0329(12) Uani 1 1 d . . . C34 C -0.0240(5) 0.4928(6) 0.7771(5) 0.0265(18) Uani 1 1 d . . . C35 C -0.1001(6) 0.3835(6) 0.7741(5) 0.035(2) Uani 1 1 d . . . H35 H -0.1136 0.3180 0.7242 0.042 Uiso 1 1 calc R . . C36 C -0.1561(6) 0.3733(7) 0.8464(5) 0.039(2) Uani 1 1 d . . . H36 H -0.2071 0.3006 0.8448 0.047 Uiso 1 1 calc R . . C37 C -0.1360(6) 0.4708(7) 0.9209(5) 0.037(2) Uani 1 1 d . . . H37 H -0.1734 0.4632 0.9691 0.044 Uiso 1 1 calc R . . C38 C -0.0605(6) 0.5797(6) 0.9239(5) 0.0290(18) Uani 1 1 d . . . C39 C -0.0085(6) 0.5894(6) 0.8502(5) 0.0252(17) Uani 1 1 d . . . H39 H 0.0380 0.6623 0.8496 0.030 Uiso 1 1 calc R . . C40 C -0.0375(7) 0.6832(6) 1.0064(5) 0.0340(19) Uani 1 1 d . . . O41 O -0.1039(5) 0.6816(5) 1.0572(4) 0.0557(16) Uani 1 1 d . . . N42 N 0.0614(5) 0.7777(5) 1.0198(4) 0.0370(16) Uani 1 1 d . . . H42 H 0.1081 0.7690 0.9869 0.044 Uiso 1 1 calc R . . C43 C 0.0950(6) 0.8901(6) 1.0834(5) 0.0315(19) Uani 1 1 d . . . C44 C 0.0146(7) 0.9341(7) 1.0952(5) 0.044(2) Uani 1 1 d . . . H44 H -0.0637 0.8884 1.0630 0.053 Uiso 1 1 calc R . . C45 C 0.0546(7) 1.0462(7) 1.1556(5) 0.044(2) Uani 1 1 d . . . H45 H 0.0038 1.0778 1.1644 0.052 Uiso 1 1 calc R . . C46 C 0.1703(6) 1.1105(7) 1.2026(5) 0.036(2) Uani 1 1 d . . . H46 H 0.1962 1.1858 1.2435 0.043 Uiso 1 1 calc R . . N47 N 0.2480(5) 1.0708(5) 1.1928(4) 0.0235(14) Uani 1 1 d . . . C48 C 0.2077(6) 0.9602(6) 1.1344(5) 0.0269(18) Uani 1 1 d . . . H48 H 0.2602 0.9303 1.1290 0.032 Uiso 1 1 calc R . . O49 O 0.5287(5) 0.9104(5) 0.8649(4) 0.0322(12) Uani 1 1 d D . . O50 O 0.6369(4) 0.7435(4) 0.5915(3) 0.0312(12) Uani 1 1 d D . . O51 O 0.2447(4) 0.7517(4) 0.9339(4) 0.0463(14) Uani 1 1 d . . . O52A O 0.8290(9) 0.7059(9) 0.5956(7) 0.033(3) Uiso 0.52 1 d P . 1 C53A C 0.8691(16) 0.6409(16) 0.6449(14) 0.066(5) Uiso 0.52 1 d P . 1 O52B O 0.8609(11) 0.7672(12) 0.5920(8) 0.053(4) Uiso 0.48 1 d P . 2 C53B C 0.903(3) 0.685(3) 0.605(2) 0.116(10) Uiso 0.48 1 d P . 2 O54A O 0.0241(10) 0.8575(10) 0.2868(8) 0.064(3) Uiso 0.52 1 d P . . O54B O 0.0723(12) 0.7999(11) 0.4406(9) 0.056(4) Uiso 0.40 1 d P . . O54C O -0.0869(13) 1.0134(12) 0.5544(10) 0.061(4) Uiso 0.40 1 d P . . O54D O 0.025(2) 0.877(2) 0.369(2) 0.079(8) Uiso 0.24 1 d P . . O55A O 0.3895(10) 0.7258(9) 0.0603(8) 0.059(3) Uiso 0.50 1 d P . . O55B O 0.4252(10) 0.7223(10) -0.0234(8) 0.061(3) Uiso 0.50 1 d P . . O56A O 0.0255(9) 0.8858(10) 0.5992(8) 0.059(3) Uiso 0.52 1 d P . . O56B O 0.0422(12) 0.9746(13) 0.6259(10) 0.079(4) Uiso 0.48 1 d P . . H49A H 0.568(5) 0.937(5) 0.9191(17) 0.02(2) Uiso 1 1 d D . . H49B H 0.472(3) 0.920(6) 0.861(5) 0.03(2) Uiso 1 1 d D . . H50A H 0.701(3) 0.749(7) 0.597(6) 0.050 Uiso 1 1 d D . . H50B H 0.620(7) 0.752(7) 0.542(3) 0.050 Uiso 1 1 d 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 Cu1 0.0219(5) 0.0282(6) 0.0243(5) 0.0106(4) 0.0061(4) 0.0116(4) Si1 0.0200(11) 0.0251(11) 0.0263(12) 0.0078(9) 0.0053(9) 0.0093(10) F1 0.059(3) 0.053(3) 0.044(3) 0.025(2) -0.009(2) 0.012(3) F2 0.036(3) 0.032(2) 0.060(3) 0.006(2) 0.024(2) 0.016(2) F3 0.059(3) 0.034(3) 0.032(3) 0.017(2) -0.003(2) 0.001(2) F4 0.022(2) 0.029(2) 0.062(3) 0.013(2) 0.015(2) 0.009(2) F5 0.040(3) 0.025(2) 0.082(3) 0.011(2) 0.034(2) 0.013(2) F6 0.026(2) 0.035(2) 0.046(3) 0.018(2) 0.013(2) 0.010(2) N1 0.020(3) 0.029(3) 0.022(3) 0.012(3) 0.005(3) 0.012(3) C2 0.018(4) 0.023(4) 0.032(4) 0.007(4) 0.006(4) 0.009(3) C3 0.028(5) 0.028(5) 0.031(4) 0.011(4) 0.015(4) 0.009(4) C4 0.028(5) 0.030(4) 0.032(4) 0.018(4) 0.011(4) 0.012(4) C5 0.027(4) 0.028(4) 0.021(4) 0.008(4) 0.007(4) 0.015(4) C6 0.030(5) 0.032(5) 0.022(4) 0.012(4) 0.011(3) 0.014(4) N7 0.040(4) 0.040(4) 0.034(4) 0.022(3) 0.026(3) 0.025(3) C8 0.030(5) 0.030(5) 0.030(5) 0.012(4) 0.006(4) 0.015(4) O9 0.047(3) 0.051(3) 0.027(3) 0.024(3) 0.022(3) 0.032(3) C10 0.034(5) 0.036(5) 0.037(5) 0.023(4) 0.021(4) 0.027(4) C11 0.043(5) 0.045(5) 0.032(5) 0.022(4) 0.019(4) 0.028(4) C12 0.050(5) 0.057(5) 0.037(5) 0.027(4) 0.020(4) 0.039(5) C13 0.044(5) 0.030(4) 0.041(5) 0.018(4) 0.023(4) 0.028(4) C14 0.033(5) 0.030(4) 0.037(5) 0.024(4) 0.017(4) 0.020(4) C15 0.035(5) 0.028(4) 0.035(5) 0.023(4) 0.014(4) 0.020(4) C16 0.031(5) 0.023(5) 0.042(5) 0.019(4) 0.021(4) 0.016(4) O17 0.046(3) 0.026(3) 0.045(3) 0.019(3) 0.018(3) 0.020(3) N18 0.040(4) 0.023(3) 0.032(4) 0.014(3) 0.013(3) 0.018(3) C19 0.021(4) 0.028(4) 0.031(5) 0.009(4) 0.005(3) 0.015(4) C20 0.043(5) 0.033(5) 0.042(6) 0.019(4) 0.015(4) 0.023(4) C21 0.046(5) 0.020(4) 0.035(5) 0.007(4) 0.016(4) 0.014(4) C22 0.025(4) 0.036(5) 0.024(4) 0.010(4) 0.006(3) 0.009(4) N23 0.023(3) 0.027(4) 0.019(4) 0.010(3) 0.005(3) 0.009(3) C24 0.025(4) 0.027(4) 0.028(5) 0.010(4) 0.008(3) 0.017(4) N25 0.018(3) 0.026(3) 0.021(4) 0.009(3) 0.008(3) 0.010(3) C26 0.035(5) 0.043(5) 0.021(5) 0.016(4) 0.012(4) 0.018(4) C27 0.026(5) 0.051(5) 0.021(4) 0.011(4) -0.006(4) 0.006(4) C28 0.025(5) 0.038(5) 0.032(5) 0.016(4) 0.004(4) 0.001(4) C29 0.026(5) 0.026(4) 0.023(5) 0.011(3) 0.004(4) 0.011(4) C30 0.026(5) 0.025(4) 0.022(4) 0.008(3) 0.003(4) 0.013(4) N31 0.028(4) 0.034(4) 0.021(3) 0.009(3) 0.010(3) 0.009(3) C32 0.024(5) 0.025(4) 0.024(5) 0.005(4) -0.001(4) 0.008(4) O33 0.029(3) 0.033(3) 0.025(3) 0.007(3) 0.006(2) 0.006(2) C34 0.013(4) 0.026(5) 0.029(4) 0.011(4) 0.001(3) -0.001(4) C35 0.027(5) 0.029(5) 0.038(5) 0.008(4) 0.006(4) 0.006(4) C36 0.028(5) 0.032(5) 0.047(5) 0.015(4) 0.014(4) 0.003(4) C37 0.029(5) 0.048(6) 0.032(5) 0.014(4) 0.007(4) 0.016(4) C38 0.027(4) 0.028(5) 0.033(5) 0.013(4) 0.010(4) 0.012(4) C39 0.023(4) 0.017(4) 0.029(4) 0.008(4) 0.003(4) 0.005(3) C40 0.029(5) 0.040(5) 0.034(5) 0.015(4) 0.009(4) 0.016(5) O41 0.069(4) 0.051(4) 0.062(4) 0.026(3) 0.047(4) 0.029(3) N42 0.022(4) 0.043(4) 0.030(4) -0.005(3) 0.012(3) 0.008(4) C43 0.025(5) 0.040(5) 0.025(4) 0.005(4) 0.008(4) 0.015(4) C44 0.029(5) 0.059(6) 0.034(5) 0.005(5) 0.005(4) 0.019(5) C45 0.033(6) 0.056(6) 0.036(5) 0.002(5) 0.005(4) 0.025(5) C46 0.027(5) 0.041(5) 0.032(5) 0.005(4) 0.006(4) 0.014(4) N47 0.023(3) 0.036(4) 0.020(3) 0.013(3) 0.008(3) 0.019(3) C48 0.022(5) 0.032(5) 0.023(4) 0.006(4) 0.005(4) 0.012(4) O49 0.025(3) 0.048(3) 0.025(4) 0.007(3) 0.003(3) 0.022(3) O50 0.031(3) 0.045(3) 0.025(3) 0.017(3) 0.009(3) 0.021(3) O51 0.044(3) 0.045(3) 0.045(3) 0.014(3) 0.015(3) 0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N47 2.015(6) 2_677 ? Cu1 N25 2.022(5) . ? Cu1 N23 2.027(5) 2_677 ? Cu1 N1 2.043(5) . ? Cu1 O49 2.341(5) . ? Si1 F4 1.648(4) . ? Si1 F1 1.661(5) . ? Si1 F5 1.664(4) . ? Si1 F2 1.680(4) . ? Si1 F3 1.692(4) . ? Si1 F6 1.709(4) . ? N1 C2 1.336(8) . ? N1 C6 1.348(8) . ? C2 C3 1.372(9) . ? C2 H2 0.9300 . ? C3 C4 1.375(9) . ? C3 H3 0.9300 . ? C4 C5 1.381(9) . ? C4 H4 0.9300 . ? C5 C6 1.395(9) . ? C5 N7 1.402(8) . ? C6 H6 0.9300 . ? N7 C8 1.359(8) . ? N7 H7 0.8600 . ? C8 O9 1.225(8) . ? C8 C10 1.498(10) . ? C10 C11 1.383(9) . ? C10 C15 1.394(9) . ? C11 C12 1.385(10) . ? C11 H11 0.9300 . ? C12 C13 1.374(10) . ? C12 H12 0.9300 . ? C13 C14 1.392(9) . ? C13 H13 0.9300 . ? C14 C15 1.386(9) . ? C14 C16 1.504(10) . ? C15 H15 0.9300 . ? C16 O17 1.231(8) . ? C16 N18 1.350(8) . ? N18 C19 1.405(8) . ? N18 H18 0.8600 . ? C19 C24 1.389(9) . ? C19 C20 1.401(9) . ? C20 C21 1.382(10) . ? C20 H20 0.9300 . ? C21 C22 1.371(9) . ? C21 H21 0.9300 . ? C22 N23 1.340(8) . ? C22 H22 0.9300 . ? N23 C24 1.328(8) . ? N23 Cu1 2.027(5) 2_677 ? C24 H24 0.9300 . ? N25 C26 1.339(8) . ? N25 C30 1.344(8) . ? C26 C27 1.365(10) . ? C26 H26 0.9300 . ? C27 C28 1.383(10) . ? C27 H27 0.9300 . ? C28 C29 1.384(9) . ? C28 H28 0.9300 . ? C29 C30 1.377(9) . ? C29 N31 1.426(8) . ? C30 H30 0.9300 . ? N31 C32 1.369(8) . ? N31 H31 0.8600 . ? C32 O33 1.224(8) . ? C32 C34 1.495(10) . ? C34 C39 1.386(9) . ? C34 C35 1.393(9) . ? C35 C36 1.393(10) . ? C35 H35 0.9300 . ? C36 C37 1.385(10) . ? C36 H36 0.9300 . ? C37 C38 1.387(10) . ? C37 H37 0.9300 . ? C38 C39 1.382(9) . ? C38 C40 1.490(10) . ? C39 H39 0.9300 . ? C40 O41 1.229(8) . ? C40 N42 1.344(9) . ? N42 C43 1.413(9) . ? N42 H42 0.8600 . ? C43 C48 1.358(9) . ? C43 C44 1.411(10) . ? C44 C45 1.379(10) . ? C44 H44 0.9300 . ? C45 C46 1.369(10) . ? C45 H45 0.9300 . ? C46 N47 1.335(8) . ? C46 H46 0.9300 . ? N47 C48 1.353(8) . ? N47 Cu1 2.015(5) 2_677 ? C48 H48 0.9300 . ? O49 H49A 0.798(11) . ? O49 H49B 0.797(11) . ? O50 H50A 0.800(11) . ? O50 H50B 0.798(11) . ? O51 O51 0.000(11) 1 ? O52A O52A 0.00(3) 1 ? O52A C53A 1.49(2) . ? C53A O52A 1.49(2) 1 ? O52B O52B 0.00000(12) 1 ? O52B C53B 1.47(3) . ? C53B O52B 1.47(3) 1 ? O54A O54D 1.19(3) . ? O54C O54D 1.43(3) 2_576 ? O54D O54C 1.43(3) 2_576 ? O55A O55B 1.393(15) . ? O56A O56B 1.078(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N47 Cu1 N25 178.3(2) 2_677 . ? N47 Cu1 N23 89.0(2) 2_677 2_677 ? N25 Cu1 N23 90.3(2) . 2_677 ? N47 Cu1 N1 90.3(2) 2_677 . ? N25 Cu1 N1 90.5(2) . . ? N23 Cu1 N1 176.0(2) 2_677 . ? N47 Cu1 O49 90.0(2) 2_677 . ? N25 Cu1 O49 88.5(2) . . ? N23 Cu1 O49 93.2(2) 2_677 . ? N1 Cu1 O49 90.7(2) . . ? F4 Si1 F1 92.9(2) . . ? F4 Si1 F5 92.8(2) . . ? F1 Si1 F5 91.4(3) . . ? F4 Si1 F2 90.1(2) . . ? F1 Si1 F2 90.2(2) . . ? F5 Si1 F2 176.6(2) . . ? F4 Si1 F3 90.4(2) . . ? F1 Si1 F3 176.3(3) . . ? F5 Si1 F3 90.1(2) . . ? F2 Si1 F3 88.1(2) . . ? F4 Si1 F6 178.5(2) . . ? F1 Si1 F6 87.6(2) . . ? F5 Si1 F6 88.6(2) . . ? F2 Si1 F6 88.6(2) . . ? F3 Si1 F6 89.0(2) . . ? C2 N1 C6 118.0(6) . . ? C2 N1 Cu1 121.1(4) . . ? C6 N1 Cu1 120.9(4) . . ? N1 C2 C3 122.3(6) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C2 C3 C4 120.0(6) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.0(6) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 117.9(6) . . ? C4 C5 N7 124.5(6) . . ? C6 C5 N7 117.6(6) . . ? N1 C6 C5 122.9(6) . . ? N1 C6 H6 118.6 . . ? C5 C6 H6 118.6 . . ? C8 N7 C5 126.3(6) . . ? C8 N7 H7 116.9 . . ? C5 N7 H7 116.9 . . ? O9 C8 N7 122.3(6) . . ? O9 C8 C10 121.3(6) . . ? N7 C8 C10 116.3(6) . . ? C11 C10 C15 119.1(6) . . ? C11 C10 C8 118.6(6) . . ? C15 C10 C8 121.6(6) . . ? C10 C11 C12 120.5(7) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 120.1(7) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.3(6) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.3(6) . . ? C15 C14 C16 121.7(6) . . ? C13 C14 C16 118.5(6) . . ? C14 C15 C10 120.6(6) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? O17 C16 N18 123.6(7) . . ? O17 C16 C14 120.5(6) . . ? N18 C16 C14 115.8(6) . . ? C16 N18 C19 126.3(6) . . ? C16 N18 H18 116.8 . . ? C19 N18 H18 116.8 . . ? C24 C19 C20 117.3(6) . . ? C24 C19 N18 118.1(6) . . ? C20 C19 N18 124.6(6) . . ? C21 C20 C19 118.8(7) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C22 C21 C20 119.5(7) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? N23 C22 C21 122.2(6) . . ? N23 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C24 N23 C22 118.6(6) . . ? C24 N23 Cu1 121.4(4) . 2_677 ? C22 N23 Cu1 119.8(5) . 2_677 ? N23 C24 C19 123.4(6) . . ? N23 C24 H24 118.3 . . ? C19 C24 H24 118.3 . . ? C26 N25 C30 117.7(6) . . ? C26 N25 Cu1 122.2(5) . . ? C30 N25 Cu1 119.9(4) . . ? N25 C26 C27 122.4(7) . . ? N25 C26 H26 118.8 . . ? C27 C26 H26 118.8 . . ? C26 C27 C28 120.6(7) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C29 117.0(7) . . ? C27 C28 H28 121.5 . . ? C29 C28 H28 121.5 . . ? C30 C29 C28 119.7(6) . . ? C30 C29 N31 118.1(6) . . ? C28 C29 N31 122.1(6) . . ? N25 C30 C29 122.6(6) . . ? N25 C30 H30 118.7 . . ? C29 C30 H30 118.7 . . ? C32 N31 C29 125.8(6) . . ? C32 N31 H31 117.1 . . ? C29 N31 H31 117.1 . . ? O33 C32 N31 122.3(6) . . ? O33 C32 C34 123.3(6) . . ? N31 C32 C34 114.4(6) . . ? C39 C34 C35 119.3(7) . . ? C39 C34 C32 122.0(6) . . ? C35 C34 C32 118.7(6) . . ? C36 C35 C34 119.5(7) . . ? C36 C35 H35 120.3 . . ? C34 C35 H35 120.3 . . ? C37 C36 C35 120.3(7) . . ? C37 C36 H36 119.8 . . ? C35 C36 H36 119.8 . . ? C36 C37 C38 120.4(7) . . ? C36 C37 H37 119.8 . . ? C38 C37 H37 119.8 . . ? C39 C38 C37 118.9(7) . . ? C39 C38 C40 121.7(7) . . ? C37 C38 C40 119.4(7) . . ? C38 C39 C34 121.5(6) . . ? C38 C39 H39 119.2 . . ? C34 C39 H39 119.2 . . ? O41 C40 N42 123.2(7) . . ? O41 C40 C38 122.4(7) . . ? N42 C40 C38 114.4(7) . . ? C40 N42 C43 125.6(6) . . ? C40 N42 H42 117.2 . . ? C43 N42 H42 117.2 . . ? C48 C43 C44 117.8(7) . . ? C48 C43 N42 120.3(6) . . ? C44 C43 N42 121.8(7) . . ? C45 C44 C43 118.6(7) . . ? C45 C44 H44 120.7 . . ? C43 C44 H44 120.7 . . ? C46 C45 C44 119.0(7) . . ? C46 C45 H45 120.5 . . ? C44 C45 H45 120.5 . . ? N47 C46 C45 123.5(7) . . ? N47 C46 H46 118.2 . . ? C45 C46 H46 118.2 . . ? C46 N47 C48 117.0(6) . . ? C46 N47 Cu1 120.9(5) . 2_677 ? C48 N47 Cu1 122.1(4) . 2_677 ? N47 C48 C43 124.0(6) . . ? N47 C48 H48 118.0 . . ? C43 C48 H48 118.0 . . ? Cu1 O49 H49A 124(5) . . ? Cu1 O49 H49B 125(5) . . ? H49A O49 H49B 112(7) . . ? H50A O50 H50B 106(8) . . ? O52A O52A C53A 0(10) 1 . ? O52A C53A O52A 0.0(11) 1 . ? O52B O52B C53B 0(10) 1 . ? O52B C53B O52B 0.0(14) 1 . ? O54A O54D O54C 127(2) . 2_576 ? 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 N7 H7 F6 0.86 2.11 2.903(7) 153.5 1_565 N7 H7 F1 0.86 2.37 3.104(7) 142.9 1_565 N18 H18 F5 0.86 2.02 2.831(7) 157.9 1_565 N31 H31 O51 0.86 2.10 2.961(8) 174.7 1 N42 H42 O51 0.86 2.12 2.969(8) 167.8 1 O49 H49A F3 0.798(11) 1.862(15) 2.656(7) 173(7) 2_667 O49 H49B F2 0.797(11) 1.99(3) 2.739(7) 155(7) 1_565 O50 H50A O52A 0.800(11) 1.99(3) 2.754(11) 161(8) 1 O50 H50A O52B 0.800(11) 2.02(2) 2.817(13) 171(8) 1 O50 H50B O9 0.798(11) 1.983(17) 2.775(7) 171(8) 2_676 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 20.58 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.959 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.083 #END data_4a _database_code_depnum_ccdc_archive 'CCDC 739009' #TrackingRef '- CIFS_FINAL.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H39.40 Cu N10 O15.70' _chemical_formula_weight 926.92 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M Cm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' _cell_length_a 13.3131(12) _cell_length_b 21.518(3) _cell_length_c 8.2174(10) _cell_angle_alpha 90.00 _cell_angle_beta 122.982(5) _cell_angle_gamma 90.00 _cell_volume 1974.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour VIOLET _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.641 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8826 _exptl_absorpt_correction_T_max 0.9505 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7426 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0677 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.25 _reflns_number_total 3735 _reflns_number_gt 3413 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX II' _computing_cell_refinement 'BRUKER SMART APEX II' _computing_data_reduction 'BRUKER SMART APEX SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'MERCURY 2.3' _computing_publication_material 'BRUKER SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0882P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.498(16) _refine_ls_number_reflns 3735 _refine_ls_number_parameters 279 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Cu1 Cu -0.08178(5) 0.5000 -0.00711(6) 0.02080(17) Uani 1 2 d S . . N1 N 0.0382(3) 0.43438(16) 0.0295(5) 0.0219(7) Uani 1 1 d . . . C2 C 0.0530(4) 0.41829(17) -0.1145(6) 0.0248(8) Uani 1 1 d . . . H2 H 0.0049 0.4368 -0.2356 0.030 Uiso 1 1 calc R . . C3 C 0.1362(4) 0.37569(18) -0.0883(6) 0.0265(8) Uani 1 1 d . . . H3 H 0.1437 0.3649 -0.1908 0.032 Uiso 1 1 calc R . . C4 C 0.2093(4) 0.34862(18) 0.0913(6) 0.0261(8) Uani 1 1 d . . . H4 H 0.2671 0.3197 0.1118 0.031 Uiso 1 1 calc R . . C5 C 0.1953(3) 0.36518(17) 0.2415(6) 0.0225(8) Uani 1 1 d . . . C6 C 0.1073(4) 0.40757(17) 0.2044(6) 0.0224(8) Uani 1 1 d . . . H6 H 0.0956 0.4178 0.3029 0.027 Uiso 1 1 calc R . . N7 N 0.2682(3) 0.33720(15) 0.4245(5) 0.0242(7) Uani 1 1 d . . . H7 H 0.2945 0.3003 0.4294 0.029 Uiso 1 1 calc R . . C8 C 0.2998(4) 0.36562(18) 0.5959(6) 0.0255(8) Uani 1 1 d . . . O9 O 0.2715(3) 0.41813(14) 0.6030(5) 0.0412(8) Uani 1 1 d . . . C10 C 0.3729(3) 0.32721(18) 0.7752(5) 0.0239(8) Uani 1 1 d . . . C11 C 0.3712(3) 0.26354(18) 0.7742(5) 0.0251(8) Uani 1 1 d . . . H11 H 0.3259 0.2422 0.6575 0.030 Uiso 1 1 calc R . . C12 C 0.4373(4) 0.23079(17) 0.9481(5) 0.0265(8) Uani 1 1 d . . . H12 H 0.4362 0.1876 0.9476 0.032 Uiso 1 1 calc R . . C13 C 0.5053(3) 0.26307(17) 1.1234(5) 0.0240(8) Uani 1 1 d . . . H13 H 0.5493 0.2414 1.2398 0.029 Uiso 1 1 calc R . . C14 C 0.5070(3) 0.32713(18) 1.1229(5) 0.0242(8) Uani 1 1 d . . . C15 C 0.4412(4) 0.35949(17) 0.9503(5) 0.0248(8) Uani 1 1 d . . . H15 H 0.4423 0.4027 0.9506 0.030 Uiso 1 1 calc R . . C16 C 0.5815(3) 0.36389(18) 1.3052(5) 0.0236(8) Uani 1 1 d . . . O17 O 0.6254(3) 0.41399(13) 1.3059(4) 0.0310(6) Uani 1 1 d . . . N18 N 0.5934(3) 0.33754(15) 1.4656(5) 0.0251(7) Uani 1 1 d . . . H18 H 0.5560 0.3030 1.4474 0.030 Uiso 1 1 calc R . . C19 C 0.6596(3) 0.35999(18) 1.6580(5) 0.0238(8) Uani 1 1 d . . . C20 C 0.6503(4) 0.32719(18) 1.7944(6) 0.0257(8) Uani 1 1 d . . . H20 H 0.6010 0.2925 1.7580 0.031 Uiso 1 1 calc R . . C21 C 0.7155(4) 0.34689(19) 1.9860(6) 0.0271(8) Uani 1 1 d . . . H21 H 0.7107 0.3253 2.0796 0.033 Uiso 1 1 calc R . . C22 C 0.7869(4) 0.39819(19) 2.0361(6) 0.0257(8) Uani 1 1 d . . . H22 H 0.8311 0.4108 2.1651 0.031 Uiso 1 1 calc R . . N23 N 0.7952(3) 0.43085(15) 1.9057(5) 0.0210(7) Uani 1 1 d . . . C24 C 0.7330(4) 0.41213(18) 1.7181(6) 0.0242(8) Uani 1 1 d . . . H24 H 0.7395 0.4346 1.6276 0.029 Uiso 1 1 calc R . . O25 O -0.0354(4) 0.5000 0.3025(6) 0.0260(8) Uani 1 2 d S . . H25 H -0.0470 0.5347 0.3301 0.039 Uiso 0.50 1 calc PR . . N26 N 0.4403(3) 0.19093(15) 0.4522(4) 0.0280(7) Uani 1 1 d . . . O27 O 0.5313(4) 0.16892(18) 0.4706(5) 0.0541(11) Uani 1 1 d . . . O28 O 0.3683(4) 0.15802(14) 0.4635(5) 0.0440(8) Uani 1 1 d . . . O29 O 0.4201(3) 0.24803(12) 0.4205(5) 0.0304(6) Uani 1 1 d . . . O30 O 0.3090(4) 0.0000 0.4210(7) 0.0374(10) Uani 1 2 d S . . O31 O 0.6470(4) 1.0000 0.6772(7) 0.0401(11) Uani 1 2 d S . . 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 Cu1 0.0177(3) 0.0300(3) 0.0107(3) 0.000 0.0052(2) 0.000 N1 0.0189(16) 0.0301(15) 0.0120(16) 0.0005(12) 0.0054(13) -0.0001(12) C2 0.027(2) 0.0312(18) 0.016(2) -0.0004(14) 0.0109(17) -0.0028(15) C3 0.030(2) 0.0369(19) 0.0144(19) 0.0005(15) 0.0136(17) 0.0021(16) C4 0.028(2) 0.0316(18) 0.0191(19) 0.0016(14) 0.0128(17) 0.0065(15) C5 0.0195(18) 0.0301(18) 0.0134(18) -0.0023(14) 0.0060(15) -0.0025(14) C6 0.0221(19) 0.0318(19) 0.0123(19) -0.0002(14) 0.0087(16) -0.0033(14) N7 0.0247(17) 0.0326(15) 0.0123(16) 0.0026(12) 0.0081(14) 0.0063(13) C8 0.0249(19) 0.0322(19) 0.0150(18) 0.0005(15) 0.0080(16) 0.0051(15) O9 0.050(2) 0.0416(16) 0.0148(14) -0.0013(12) 0.0068(14) 0.0154(14) C10 0.0169(18) 0.040(2) 0.0108(17) -0.0019(14) 0.0048(15) 0.0017(15) C11 0.0230(19) 0.040(2) 0.0089(17) -0.0011(14) 0.0066(16) 0.0002(15) C12 0.030(2) 0.0311(17) 0.0148(19) 0.0013(14) 0.0097(17) 0.0017(16) C13 0.0206(18) 0.0369(19) 0.0096(17) 0.0011(14) 0.0051(15) 0.0026(15) C14 0.0211(18) 0.0355(18) 0.0142(19) 0.0005(14) 0.0085(16) -0.0010(15) C15 0.0252(19) 0.0315(17) 0.0153(19) 0.0014(14) 0.0094(16) 0.0040(15) C16 0.0186(17) 0.0362(19) 0.0116(18) -0.0018(14) 0.0055(15) -0.0021(15) O17 0.0299(16) 0.0380(14) 0.0152(14) 0.0004(11) 0.0058(13) -0.0076(12) N18 0.0258(17) 0.0319(16) 0.0107(15) -0.0028(12) 0.0054(14) -0.0088(13) C19 0.0196(17) 0.038(2) 0.0106(18) -0.0019(14) 0.0064(16) -0.0014(15) C20 0.0212(19) 0.037(2) 0.0153(19) -0.0023(15) 0.0079(16) -0.0077(15) C21 0.027(2) 0.041(2) 0.0099(18) 0.0005(14) 0.0079(17) -0.0061(16) C22 0.0227(19) 0.044(2) 0.0098(18) -0.0030(15) 0.0083(16) 0.0008(16) N23 0.0190(15) 0.0298(15) 0.0137(16) -0.0024(12) 0.0086(14) -0.0016(13) C24 0.0223(19) 0.0340(19) 0.0102(19) -0.0012(14) 0.0050(16) -0.0017(15) O25 0.025(2) 0.036(2) 0.017(2) 0.000 0.0120(18) 0.000 N26 0.0334(19) 0.0361(17) 0.0098(16) -0.0001(12) 0.0087(15) 0.0090(15) O27 0.065(3) 0.073(2) 0.033(2) 0.0200(17) 0.0322(19) 0.042(2) O28 0.063(2) 0.0436(17) 0.0302(18) -0.0036(14) 0.0285(18) -0.0156(16) O29 0.0310(15) 0.0306(13) 0.0321(16) 0.0018(12) 0.0188(14) 0.0043(12) O30 0.032(2) 0.047(2) 0.040(3) 0.000 0.025(2) 0.000 O31 0.039(3) 0.058(3) 0.030(3) 0.000 0.024(2) 0.000 _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 Cu1 N1 2.028(4) . ? Cu1 N1 2.028(4) 2_565 ? Cu1 N23 2.032(3) 1_453 ? Cu1 N23 2.032(3) 2_463 ? Cu1 O25 2.267(4) . ? N1 C6 1.344(5) . ? N1 C2 1.346(6) . ? C2 C3 1.362(6) . ? C2 H2 0.9300 . ? C3 C4 1.379(5) . ? C3 H3 0.9300 . ? C4 C5 1.392(6) . ? C4 H4 0.9300 . ? C5 C6 1.382(6) . ? C5 N7 1.406(5) . ? C6 H6 0.9300 . ? N7 C8 1.374(5) . ? N7 H7 0.8600 . ? C8 O9 1.203(5) . ? C8 C10 1.497(5) . ? C10 C11 1.370(5) . ? C10 C15 1.398(5) . ? C11 C12 1.394(5) . ? C11 H11 0.9300 . ? C12 C13 1.399(5) . ? C12 H12 0.9300 . ? C13 C14 1.379(5) . ? C13 H13 0.9300 . ? C14 C15 1.383(5) . ? C14 C16 1.495(5) . ? C15 H15 0.9300 . ? C16 O17 1.225(5) . ? C16 N18 1.363(5) . ? N18 C19 1.412(5) . ? N18 H18 0.8600 . ? C19 C20 1.386(6) . ? C19 C24 1.390(5) . ? C20 C21 1.387(5) . ? C20 H20 0.9300 . ? C21 C22 1.366(6) . ? C21 H21 0.9300 . ? C22 N23 1.336(6) . ? C22 H22 0.9300 . ? N23 C24 1.354(5) . ? N23 Cu1 2.032(3) 1_657 ? C24 H24 0.9300 . ? O25 H25 0.8200 . ? N26 O27 1.231(5) . ? N26 O28 1.235(5) . ? N26 O29 1.254(4) 1 ? N26 O29 1.254(4) . ? O29 O29 0.000(9) 1 ? 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 N1 Cu1 N1 88.2(2) . 2_565 ? N1 Cu1 N23 87.77(12) . 1_453 ? N1 Cu1 N23 168.61(13) 2_565 1_453 ? N1 Cu1 N23 168.61(13) . 2_463 ? N1 Cu1 N23 87.77(12) 2_565 2_463 ? N23 Cu1 N23 94.12(19) 1_453 2_463 ? N1 Cu1 O25 97.01(12) . . ? N1 Cu1 O25 97.01(12) 2_565 . ? N23 Cu1 O25 94.06(12) 1_453 . ? N23 Cu1 O25 94.06(12) 2_463 . ? C6 N1 C2 119.2(3) . . ? C6 N1 Cu1 118.8(3) . . ? C2 N1 Cu1 121.9(3) . . ? N1 C2 C3 122.0(4) . . ? N1 C2 H2 119.0 . . ? C3 C2 H2 119.0 . . ? C2 C3 C4 119.6(4) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 118.9(4) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 118.7(3) . . ? C6 C5 N7 121.9(4) . . ? C4 C5 N7 119.4(3) . . ? N1 C6 C5 121.6(4) . . ? N1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 N7 C5 123.6(3) . . ? C8 N7 H7 118.2 . . ? C5 N7 H7 118.2 . . ? O9 C8 N7 122.6(4) . . ? O9 C8 C10 121.6(4) . . ? N7 C8 C10 115.8(3) . . ? C11 C10 C15 120.1(3) . . ? C11 C10 C8 123.1(3) . . ? C15 C10 C8 116.7(3) . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 119.7(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.3(3) . . ? C13 C14 C16 121.9(3) . . ? C15 C14 C16 117.8(3) . . ? C14 C15 C10 120.0(3) . . ? C14 C15 H15 120.0 . . ? C10 C15 H15 120.0 . . ? O17 C16 N18 123.9(3) . . ? O17 C16 C14 121.7(3) . . ? N18 C16 C14 114.4(3) . . ? C16 N18 C19 127.9(3) . . ? C16 N18 H18 116.1 . . ? C19 N18 H18 116.1 . . ? C20 C19 C24 118.6(3) . . ? C20 C19 N18 117.1(3) . . ? C24 C19 N18 124.3(4) . . ? C19 C20 C21 119.1(4) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C22 C21 C20 119.5(4) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? N23 C22 C21 122.1(4) . . ? N23 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C22 N23 C24 119.3(3) . . ? C22 N23 Cu1 120.3(3) . 1_657 ? C24 N23 Cu1 119.7(3) . 1_657 ? N23 C24 C19 121.4(4) . . ? N23 C24 H24 119.3 . . ? C19 C24 H24 119.3 . . ? Cu1 O25 H25 109.5 . . ? O27 N26 O28 121.5(4) . . ? O27 N26 O29 119.2(4) . 1 ? O28 N26 O29 119.4(4) . 1 ? O27 N26 O29 119.2(4) . . ? O28 N26 O29 119.4(4) . . ? O29 N26 O29 0.0(3) 1 . ? O29 O29 N26 0(10) 1 . ? 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 N7 H7 O29 0.86 2.05 2.801(4) 145.4 1 N18 H18 O29 0.86 2.07 2.870(4) 154.3 1_556 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 1.285 _refine_diff_density_min -1.251 _refine_diff_density_rms 0.098 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 -0.054 0.000 -0.519 111.5 27.0 2 0.446 0.500 -0.519 111.5 27.0 _platon_squeeze_details ; ? ; #END data_1b _database_code_depnum_ccdc_archive 'CCDC 739010' #TrackingRef '- CIFS_FINAL.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 Cu N4 O13 S' _chemical_formula_weight 604.04 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1978(4) _cell_length_b 16.6218(10) _cell_length_c 20.5689(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.2260(10) _cell_angle_gamma 90.00 _cell_volume 2446.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour 'PALE BLUE' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1252 _exptl_absorpt_coefficient_mu 1.053 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7863 _exptl_absorpt_correction_T_max 0.9205 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23124 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4317 _reflns_number_gt 3653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'MERCURY 2.2' _computing_publication_material SHELXTL-97 _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^)+(0.0435P)^2^+0.8530P] 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 4317 _refine_ls_number_parameters 390 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0738 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.003 _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 Cu1 Cu 0.98602(3) 1.000194(14) 0.237666(12) 0.01298(10) Uani 1 1 d . . . S1 S 0.28433(7) 0.24509(3) 0.32137(2) 0.01331(13) Uani 1 1 d . . . N1 N 0.9067(2) 1.01821(10) 0.14155(8) 0.0141(4) Uani 1 1 d . . . C2 C 0.9276(3) 1.08892(12) 0.11219(10) 0.0156(5) Uani 1 1 d . . . H2 H 0.9852 1.1310 0.1364 0.019 Uiso 1 1 calc R . . C3 C 0.8665(3) 1.10133(12) 0.04713(10) 0.0152(4) Uani 1 1 d . . . H3 H 0.8815 1.1515 0.0283 0.018 Uiso 1 1 calc R . . C4 C 0.7827(3) 1.03937(13) 0.00967(10) 0.0158(5) Uani 1 1 d . . . H4 H 0.7414 1.0469 -0.0343 0.019 Uiso 1 1 calc R . . C5 C 0.7622(3) 0.96525(12) 0.03992(10) 0.0133(4) Uani 1 1 d . . . C6 C 0.8251(3) 0.95773(12) 0.10608(10) 0.0143(4) Uani 1 1 d . . . H6 H 0.8098 0.9086 0.1265 0.017 Uiso 1 1 calc R . . N7 N 0.6848(2) 0.89534(10) 0.00880(8) 0.0144(4) Uani 1 1 d . . . H7 H 0.6716 0.8543 0.0333 0.017 Uiso 1 1 calc R . . C8 C 0.6290(3) 0.88657(12) -0.05640(10) 0.0140(4) Uani 1 1 d . . . O9 O 0.6256(2) 0.94320(8) -0.09481(7) 0.0185(3) Uani 1 1 d . . . C10 C 0.5725(3) 0.80382(12) -0.07979(10) 0.0139(4) Uani 1 1 d . . . C11 C 0.4645(3) 0.79760(13) -0.14003(10) 0.0152(5) Uani 1 1 d . . . H11 H 0.4255 0.8439 -0.1629 0.018 Uiso 1 1 calc R . . C12 C 0.4149(3) 0.72296(13) -0.16585(10) 0.0177(5) Uani 1 1 d . . . H12 H 0.3429 0.7192 -0.2061 0.021 Uiso 1 1 calc R . . C13 C 0.4722(3) 0.65380(13) -0.13200(10) 0.0167(5) Uani 1 1 d . . . H13 H 0.4390 0.6037 -0.1498 0.020 Uiso 1 1 calc R . . C14 C 0.5793(3) 0.65869(12) -0.07137(10) 0.0138(4) Uani 1 1 d . . . C15 C 0.6302(3) 0.73406(12) -0.04554(10) 0.0148(4) Uani 1 1 d . . . H15 H 0.7027 0.7379 -0.0054 0.018 Uiso 1 1 calc R . . C16 C 0.6409(3) 0.58095(12) -0.03922(10) 0.0141(4) Uani 1 1 d . . . O17 O 0.6240(2) 0.51775(9) -0.06969(7) 0.0183(3) Uani 1 1 d . . . N18 N 0.7165(2) 0.58400(10) 0.02460(8) 0.0139(4) Uani 1 1 d . . . H18 H 0.7109 0.6293 0.0445 0.017 Uiso 1 1 calc R . . C19 C 0.8029(3) 0.51942(12) 0.06069(10) 0.0136(4) Uani 1 1 d . . . C20 C 0.8454(3) 0.44480(12) 0.03489(10) 0.0154(5) Uani 1 1 d . . . H20 H 0.8109 0.4329 -0.0089 0.018 Uiso 1 1 calc R . . C21 C 0.9399(3) 0.38905(12) 0.07583(10) 0.0153(4) Uani 1 1 d . . . H21 H 0.9692 0.3389 0.0596 0.018 Uiso 1 1 calc R . . C22 C 0.9909(3) 0.40728(12) 0.14053(10) 0.0151(4) Uani 1 1 d . . . H22 H 1.0578 0.3696 0.1671 0.018 Uiso 1 1 calc R . . N23 N 0.9466(2) 0.47818(10) 0.16635(8) 0.0134(4) Uani 1 1 d . . . C24 C 0.8538(3) 0.53258(12) 0.12679(10) 0.0142(4) Uani 1 1 d . . . H24 H 0.8223 0.5815 0.1447 0.017 Uiso 1 1 calc R . . O25 O 1.3021(2) 1.04326(10) 0.22457(9) 0.0190(4) Uani 1 1 d . . . O26 O 1.0800(3) 0.89076(10) 0.22044(8) 0.0168(3) Uani 1 1 d . . . O27 O 0.6780(2) 0.96016(11) 0.25387(8) 0.0192(4) Uani 1 1 d . . . O28 O 0.8998(2) 1.11170(10) 0.25636(8) 0.0159(3) Uani 1 1 d . . . O29 O 0.2770(3) 0.86171(10) 0.12278(9) 0.0210(4) Uani 1 1 d . . . O30 O 0.9089(3) 0.23091(11) 0.43840(8) 0.0236(4) Uani 1 1 d . . . O31 O 0.7060(2) 0.11565(11) 0.36031(8) 0.0193(4) Uani 1 1 d . . . O32 O 0.3894(2) 0.31859(8) 0.31136(7) 0.0197(3) Uani 1 1 d . . . O33 O 0.3867(2) 0.17350(9) 0.30247(7) 0.0191(3) Uani 1 1 d . . . O34 O 0.1012(2) 0.24837(8) 0.28065(7) 0.0174(3) Uani 1 1 d . . . O35 O 0.2546(2) 0.23881(9) 0.39127(7) 0.0217(4) Uani 1 1 d . . . H25A H 1.321(4) 1.0852(18) 0.2437(14) 0.036(8) Uiso 1 1 d . . . H25B H 1.322(3) 1.0479(15) 0.1875(14) 0.026(7) Uiso 1 1 d . . . H26A H 1.142(4) 0.8875(17) 0.1919(15) 0.042(10) Uiso 1 1 d . . . H26B H 1.025(4) 0.8560(17) 0.2217(13) 0.024(9) Uiso 1 1 d . . . H27A H 0.587(4) 0.9858(16) 0.2490(14) 0.029(8) Uiso 1 1 d . . . H27B H 0.657(3) 0.9157(17) 0.2395(12) 0.024(7) Uiso 1 1 d . . . H28A H 0.964(4) 1.1514(18) 0.2629(13) 0.037(9) Uiso 1 1 d . . . H28B H 0.845(4) 1.1100(18) 0.2840(15) 0.044(10) Uiso 1 1 d . . . H29A H 0.381(4) 0.8487(16) 0.1383(13) 0.027(8) Uiso 1 1 d . . . H29B H 0.234(4) 0.8262(18) 0.1052(15) 0.040(10) Uiso 1 1 d . . . H30A H 1.006(4) 0.2363(15) 0.4208(14) 0.029(8) Uiso 1 1 d . . . H30B H 0.852(4) 0.1959(19) 0.4209(15) 0.045(10) Uiso 1 1 d . . . H31A H 0.686(3) 0.0764(17) 0.3752(13) 0.024(8) Uiso 1 1 d . . . H31B H 0.603(4) 0.1365(16) 0.3476(13) 0.031(8) 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 Cu1 0.01864(16) 0.00938(15) 0.01033(16) -0.00040(9) -0.00109(11) 0.00030(10) S1 0.0161(3) 0.0095(3) 0.0143(3) 0.00007(19) 0.0011(2) 0.0002(2) N1 0.0159(9) 0.0133(9) 0.0132(9) -0.0002(7) 0.0013(7) 0.0002(7) C2 0.0170(11) 0.0123(11) 0.0175(11) -0.0012(9) 0.0018(9) -0.0004(9) C3 0.0174(11) 0.0112(10) 0.0172(11) 0.0027(8) 0.0032(9) 0.0006(8) C4 0.0172(11) 0.0173(11) 0.0126(11) 0.0012(9) 0.0003(8) 0.0037(9) C5 0.0123(10) 0.0132(10) 0.0145(11) -0.0001(8) 0.0015(8) 0.0017(8) C6 0.0172(11) 0.0105(10) 0.0151(11) 0.0026(8) 0.0014(9) 0.0009(8) N7 0.0203(9) 0.0112(9) 0.0113(9) 0.0008(7) -0.0003(7) -0.0016(7) C8 0.0130(10) 0.0157(11) 0.0132(11) 0.0005(9) 0.0011(8) 0.0012(8) O9 0.0263(8) 0.0152(8) 0.0133(8) 0.0025(6) -0.0010(6) 0.0001(6) C10 0.0137(11) 0.0141(11) 0.0141(11) -0.0013(8) 0.0024(8) -0.0001(8) C11 0.0161(11) 0.0164(11) 0.0131(11) 0.0032(9) 0.0012(9) 0.0023(9) C12 0.0194(12) 0.0220(12) 0.0109(11) -0.0005(9) -0.0026(9) -0.0023(9) C13 0.0170(11) 0.0169(11) 0.0163(11) -0.0027(9) 0.0024(9) -0.0017(9) C14 0.0133(10) 0.0155(11) 0.0127(10) -0.0002(8) 0.0020(8) 0.0006(9) C15 0.0140(11) 0.0190(11) 0.0110(10) 0.0004(8) 0.0001(8) 0.0002(9) C16 0.0131(10) 0.0157(11) 0.0140(11) 0.0007(9) 0.0037(8) -0.0018(8) O17 0.0220(8) 0.0140(8) 0.0178(8) -0.0027(6) -0.0025(6) -0.0009(6) N18 0.0177(9) 0.0100(9) 0.0139(9) -0.0012(7) 0.0006(7) 0.0019(7) C19 0.0134(10) 0.0124(10) 0.0152(11) 0.0031(8) 0.0025(8) -0.0009(8) C20 0.0168(11) 0.0163(11) 0.0133(11) -0.0010(9) 0.0021(9) -0.0025(9) C21 0.0165(11) 0.0112(10) 0.0188(11) -0.0022(9) 0.0044(9) -0.0011(9) C22 0.0149(10) 0.0121(11) 0.0181(11) 0.0008(9) 0.0013(9) -0.0002(9) N23 0.0153(9) 0.0119(9) 0.0128(9) 0.0001(7) 0.0008(7) -0.0022(7) C24 0.0167(11) 0.0106(10) 0.0153(11) 0.0000(8) 0.0023(9) -0.0002(9) O25 0.0264(9) 0.0181(9) 0.0128(9) -0.0028(7) 0.0034(7) -0.0026(7) O26 0.0212(9) 0.0118(9) 0.0176(9) -0.0012(7) 0.0031(7) -0.0030(7) O27 0.0203(9) 0.0143(9) 0.0228(9) -0.0015(7) 0.0007(7) -0.0013(8) O28 0.0200(9) 0.0115(8) 0.0162(9) -0.0014(6) 0.0018(7) -0.0014(7) O29 0.0224(10) 0.0187(9) 0.0213(9) 0.0014(7) -0.0001(7) 0.0033(8) O30 0.0242(10) 0.0247(10) 0.0221(9) -0.0007(8) 0.0027(8) -0.0029(8) O31 0.0201(9) 0.0147(9) 0.0228(9) 0.0050(7) 0.0016(7) 0.0014(7) O32 0.0206(8) 0.0123(8) 0.0257(9) 0.0022(6) -0.0003(7) -0.0028(6) O33 0.0208(8) 0.0132(8) 0.0227(8) -0.0030(6) -0.0005(7) 0.0036(6) O34 0.0167(8) 0.0140(8) 0.0206(8) -0.0005(6) -0.0028(6) 0.0002(6) O35 0.0278(9) 0.0225(8) 0.0150(8) 0.0011(6) 0.0031(7) 0.0010(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O26 1.9860(16) . ? Cu1 O28 2.0050(16) . ? Cu1 N23 2.0147(17) 2_755 ? Cu1 N1 2.0197(17) . ? Cu1 O27 2.3730(17) . ? Cu1 O25 2.4278(16) . ? S1 O32 1.4631(15) . ? S1 O33 1.4739(15) 1 ? S1 O33 1.4739(15) . ? S1 O35 1.4802(16) . ? S1 O34 1.4839(15) . ? N1 C2 1.337(3) . ? N1 C6 1.340(3) . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 C4 1.385(3) . ? C3 H3 0.9300 . ? C4 C5 1.395(3) . ? C4 H4 0.9300 . ? C5 C6 1.392(3) . ? C5 N7 1.412(3) . ? C6 H6 0.9300 . ? N7 C8 1.365(3) . ? N7 H7 0.8600 . ? C8 O9 1.228(2) . ? C8 C10 1.499(3) . ? C10 C11 1.394(3) . ? C10 C15 1.396(3) . ? C11 C12 1.381(3) . ? C11 H11 0.9300 . ? C12 C13 1.383(3) . ? C12 H12 0.9300 . ? C13 C14 1.395(3) . ? C13 H13 0.9300 . ? C14 C15 1.394(3) . ? C14 C16 1.497(3) . ? C15 H15 0.9300 . ? C16 O17 1.223(2) . ? C16 N18 1.366(3) . ? N18 C19 1.411(3) . ? N18 H18 0.8600 . ? C19 C24 1.387(3) . ? C19 C20 1.396(3) . ? C20 C21 1.381(3) . ? C20 H20 0.9300 . ? C21 C22 1.375(3) . ? C21 H21 0.9300 . ? C22 N23 1.345(3) . ? C22 H22 0.9300 . ? N23 C24 1.344(3) . ? N23 Cu1 2.0148(17) 2_745 ? C24 H24 0.9300 . ? O25 H25A 0.81(3) . ? O25 H25B 0.80(3) . ? O26 H26A 0.78(3) . ? O26 H26B 0.70(3) . ? O27 H27A 0.78(3) . ? O27 H27B 0.80(3) . ? O28 H28A 0.81(3) . ? O28 H28B 0.73(3) . ? O29 H29A 0.81(3) . ? O29 H29B 0.74(3) . ? O30 H30A 0.83(3) . ? O30 H30B 0.78(3) . ? O31 H31A 0.74(3) . ? O31 H31B 0.84(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O26 Cu1 O28 178.07(7) . . ? O26 Cu1 N23 87.60(7) . 2_755 ? O28 Cu1 N23 91.52(7) . 2_755 ? O26 Cu1 N1 91.54(7) . . ? O28 Cu1 N1 89.43(7) . . ? N23 Cu1 N1 176.92(7) 2_755 . ? O26 Cu1 O27 96.31(7) . . ? O28 Cu1 O27 85.34(7) . . ? N23 Cu1 O27 86.60(6) 2_755 . ? N1 Cu1 O27 90.56(6) . . ? O26 Cu1 O25 84.76(7) . . ? O28 Cu1 O25 93.56(7) . . ? N23 Cu1 O25 91.92(6) 2_755 . ? N1 Cu1 O25 90.95(6) . . ? O27 Cu1 O25 178.13(6) . . ? O32 S1 O33 110.86(9) . 1 ? O32 S1 O33 110.86(9) . . ? O32 S1 O35 109.09(9) . . ? O33 S1 O35 109.17(9) 1 . ? O33 S1 O35 109.17(9) . . ? O32 S1 O34 109.33(8) . . ? O33 S1 O34 108.65(8) 1 . ? O33 S1 O34 108.65(8) . . ? O35 S1 O34 109.73(9) . . ? C2 N1 C6 118.53(18) . . ? C2 N1 Cu1 122.59(14) . . ? C6 N1 Cu1 118.85(14) . . ? N1 C2 C3 122.03(19) . . ? N1 C2 H2 119.0 . . ? C3 C2 H2 119.0 . . ? C2 C3 C4 120.20(19) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 117.99(19) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? C6 C5 C4 118.44(19) . . ? C6 C5 N7 116.08(18) . . ? C4 C5 N7 125.47(19) . . ? N1 C6 C5 122.80(19) . . ? N1 C6 H6 118.6 . . ? C5 C6 H6 118.6 . . ? C8 N7 C5 126.36(18) . . ? C8 N7 H7 116.8 . . ? C5 N7 H7 116.8 . . ? O9 C8 N7 122.25(19) . . ? O9 C8 C10 120.75(18) . . ? N7 C8 C10 117.00(18) . . ? C11 C10 C15 119.58(19) . . ? C11 C10 C8 117.34(18) . . ? C15 C10 C8 123.01(18) . . ? C12 C11 C10 120.30(19) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.17(19) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 120.5(2) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 119.33(19) . . ? C15 C14 C16 123.66(18) . . ? C13 C14 C16 116.94(18) . . ? C14 C15 C10 120.16(19) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? O17 C16 N18 122.11(19) . . ? O17 C16 C14 120.47(18) . . ? N18 C16 C14 117.42(18) . . ? C16 N18 C19 125.75(18) . . ? C16 N18 H18 117.1 . . ? C19 N18 H18 117.1 . . ? C24 C19 C20 117.86(19) . . ? C24 C19 N18 116.78(18) . . ? C20 C19 N18 125.33(19) . . ? C21 C20 C19 118.57(19) . . ? C21 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? C22 C21 C20 120.29(19) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? N23 C22 C21 121.68(19) . . ? N23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C24 N23 C22 118.28(18) . . ? C24 N23 Cu1 121.45(14) . 2_745 ? C22 N23 Cu1 120.25(14) . 2_745 ? N23 C24 C19 123.26(19) . . ? N23 C24 H24 118.4 . . ? C19 C24 H24 118.4 . . ? Cu1 O25 H25A 108.3(19) . . ? Cu1 O25 H25B 113.8(18) . . ? H25A O25 H25B 110(3) . . ? Cu1 O26 H26A 116(2) . . ? Cu1 O26 H26B 123(2) . . ? H26A O26 H26B 110(3) . . ? Cu1 O27 H27A 127.8(19) . . ? Cu1 O27 H27B 110.2(18) . . ? H27A O27 H27B 110(3) . . ? Cu1 O28 H28A 127(2) . . ? Cu1 O28 H28B 109(2) . . ? H28A O28 H28B 105(3) . . ? H29A O29 H29B 107(3) . . ? H30A O30 H30B 108(3) . . ? H31A O31 H31B 107(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 N7 H7 O35 0.86 2.49 3.315(2) 161.4 2_655 N18 H18 O35 0.86 2.25 3.095(2) 168.9 2_655 O25 H25A O33 0.81(3) 1.93(3) 2.723(2) 169(3) 1_665 O25 H25B O9 0.80(3) 1.99(3) 2.783(2) 179(3) 3_775 O26 H26A O29 0.78(3) 1.86(3) 2.626(2) 170(3) 1_655 O26 H26B O34 0.70(3) 2.01(3) 2.701(2) 172(3) 2_655 O27 H27A O25 0.78(3) 2.27(3) 3.039(3) 171(3) 1_455 O27 H27B O32 0.80(3) 1.93(3) 2.726(2) 169(2) 2_655 O28 H28A O34 0.81(3) 1.90(3) 2.712(2) 176(3) 1_665 O28 H28B O31 0.73(3) 1.95(3) 2.677(2) 175(3) 1_565 O29 H29A O32 0.81(3) 1.92(3) 2.722(2) 171(3) 2_655 O29 H29B O30 0.74(3) 2.04(3) 2.781(3) 174(3) 2_655 O30 H30A O35 0.83(3) 1.95(3) 2.770(3) 171(3) 1_655 O30 H30B O31 0.78(3) 2.04(3) 2.806(3) 170(3) 1 O31 H31A O17 0.74(3) 2.01(3) 2.743(2) 169(3) 4_566 O31 H31B O33 0.84(3) 1.83(3) 2.651(2) 168(3) 1 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.409 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.058