# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Wei-Yin Sun' data_1 _database_code_depnum_ccdc_archive 'CCDC 894330' #TrackingRef '- CC-COM-07-2012-035456.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H47 Cu N13 O9' _chemical_formula_weight 785.34 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pmma ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z' 'x+1/2, -y, -z' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z' '-x-1/2, y, z' _cell_length_a 7.102(3) _cell_length_b 15.819(7) _cell_length_c 18.669(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2097.2(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour dark-green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 826 _exptl_absorpt_coefficient_mu 0.581 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8450 _exptl_absorpt_correction_T_max 0.9442 _exptl_absorpt_process_details 'SADABS; Brucker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex DUO CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10519 _diffrn_reflns_av_R_equivalents 0.1347 _diffrn_reflns_av_sigmaI/netI 0.0761 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2109 _reflns_number_gt 1540 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Restraints have been applied to the displacement of C and N atoms to control the refinement. 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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2109 _refine_ls_number_parameters 106 _refine_ls_number_restraints 111 _refine_ls_R_factor_all 0.0865 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.2337 _refine_ls_wR_factor_gt 0.2195 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 1.052 _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 0.0000 0.0000 0.0399(5) Uani 1 4 d S . . C1 C 0.2500 0.4231(4) 0.2248(4) 0.0703(15) Uani 1 2 d SU . . C2 C 0.4072(11) 0.3887(4) 0.2034(3) 0.1034(16) Uani 1 1 d U . . H2A H 0.5209 0.4147 0.2146 0.124 Uiso 1 1 calc R . . C3 C 0.4085(10) 0.3113(4) 0.1627(4) 0.0979(16) Uani 1 1 d U . . H3A H 0.5221 0.2862 0.1501 0.118 Uiso 1 1 calc R . . C4 C 0.2500 0.2768(4) 0.1436(4) 0.0617(14) Uani 1 2 d SU . . C5 C 0.2500 0.1971(3) 0.1028(3) 0.0513(12) Uani 1 2 d SU . . C6 C 0.2500 0.5000 0.3354(5) 0.0683(18) Uani 1 4 d SU . . C7 C 0.2500 0.4258(6) 0.3760(4) 0.0777(17) Uani 1 2 d SU . . H7A H 0.2500 0.3740 0.3524 0.093 Uiso 1 2 calc SR . . C8 C 0.2500 0.4268(7) 0.4493(4) 0.0933(19) Uani 1 2 d SU . . H8A H 0.2500 0.3757 0.4739 0.112 Uiso 1 2 calc SR . . C9 C 0.2500 0.5000 0.4872(6) 0.097(2) Uani 1 4 d SU . . C10 C 0.2500 0.5000 0.5650(7) 0.112(2) Uani 1 4 d SU . . N1 N 0.3402(4) 0.08936(18) 0.04618(16) 0.0444(8) Uani 1 1 d U . . N2 N 0.4062(5) 0.15617(19) 0.08154(18) 0.0510(9) Uani 1 1 d U . . N3 N 0.2500 0.5696(8) 0.6052(4) 0.128(2) Uani 1 2 d SU . . N4 N 0.2500 0.5428(7) 0.6768(4) 0.136(3) Uani 1 2 d SU . . N5 N 0.2500 0.5000 0.2637(4) 0.0660(16) Uani 1 4 d SU . . O1 O 0.7500 0.0000 0.0911(3) 0.0601(16) Uani 1 4 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 0.0347(6) 0.0236(6) 0.0615(7) 0.000 0.0036(4) 0.000 C1 0.101(4) 0.041(3) 0.069(3) -0.009(2) 0.000 0.000 C2 0.100(3) 0.072(3) 0.138(4) -0.052(3) -0.006(3) -0.008(3) C3 0.086(3) 0.068(3) 0.140(4) -0.054(3) -0.004(3) -0.005(2) C4 0.068(3) 0.032(2) 0.085(3) -0.018(2) 0.000 0.000 C5 0.053(3) 0.029(2) 0.072(3) -0.013(2) 0.000 0.000 C6 0.094(4) 0.059(4) 0.051(3) 0.000 0.000 0.000 C7 0.097(4) 0.080(4) 0.056(3) 0.012(2) 0.000 0.000 C8 0.097(4) 0.125(5) 0.058(3) 0.016(3) 0.000 0.000 C9 0.081(5) 0.158(6) 0.054(3) 0.000 0.000 0.000 C10 0.078(5) 0.201(7) 0.057(3) 0.000 0.000 0.000 N1 0.0375(15) 0.0289(14) 0.067(2) -0.0065(14) 0.0040(15) -0.0061(12) N2 0.0465(18) 0.0337(16) 0.073(2) -0.0135(14) -0.0012(16) -0.0066(14) N3 0.087(4) 0.235(7) 0.062(3) -0.020(3) 0.000 0.000 N4 0.087(4) 0.255(8) 0.066(3) -0.010(4) 0.000 0.000 N5 0.105(4) 0.041(3) 0.052(3) 0.000 0.000 0.000 O1 0.054(3) 0.064(4) 0.062(4) 0.000 0.000 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 2.007(3) 7 ? Cu1 N1 2.007(3) 3_655 ? Cu1 N1 2.007(3) . ? Cu1 N1 2.007(3) 5_655 ? Cu1 O1 2.458(4) . ? C1 C2 1.305(8) 8_655 ? C1 C2 1.305(8) . ? C1 N5 1.417(7) . ? C2 C3 1.440(7) . ? C2 H2A 0.9300 . ? C3 C4 1.301(7) . ? C3 H3A 0.9300 . ? C4 C3 1.301(7) 8_655 ? C4 C5 1.473(7) . ? C5 N2 1.344(4) 8_655 ? C5 N2 1.344(4) . ? C6 N5 1.338(12) . ? C6 C7 1.397(9) 2_565 ? C6 C7 1.397(9) . ? C7 C8 1.369(11) . ? C7 H7A 0.9300 . ? C8 C9 1.357(11) . ? C8 H8A 0.9300 . ? C9 C8 1.357(11) 2_565 ? C9 C10 1.453(16) . ? C10 N3 1.333(12) . ? C10 N3 1.333(12) 2_565 ? N1 N1 1.281(6) 8_655 ? N1 N2 1.331(4) . ? N3 N4 1.402(11) . ? N4 N4 1.35(2) 2_565 ? N5 C1 1.417(7) 2_565 ? 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 180.0(2) 7 3_655 ? N1 Cu1 N1 89.54(16) 7 . ? N1 Cu1 N1 90.46(16) 3_655 . ? N1 Cu1 N1 90.46(16) 7 5_655 ? N1 Cu1 N1 89.54(16) 3_655 5_655 ? N1 Cu1 N1 180.0(2) . 5_655 ? N1 Cu1 O1 96.39(11) 7 . ? N1 Cu1 O1 83.61(11) 3_655 . ? N1 Cu1 O1 96.39(11) . . ? N1 Cu1 O1 83.61(11) 5_655 . ? C2 C1 C2 117.6(7) 8_655 . ? C2 C1 N5 121.0(4) 8_655 . ? C2 C1 N5 121.0(4) . . ? C1 C2 C3 121.5(7) . . ? C1 C2 H2A 119.3 . . ? C3 C2 H2A 119.3 . . ? C4 C3 C2 119.7(6) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C3 119.8(7) . 8_655 ? C3 C4 C5 120.1(3) . . ? C3 C4 C5 120.1(3) 8_655 . ? N2 C5 N2 111.2(4) 8_655 . ? N2 C5 C4 124.4(2) 8_655 . ? N2 C5 C4 124.4(2) . . ? N5 C6 C7 122.8(5) . 2_565 ? N5 C6 C7 122.8(5) . . ? C7 C6 C7 114.3(9) 2_565 . ? C8 C7 C6 122.2(9) . . ? C8 C7 H7A 118.9 . . ? C6 C7 H7A 118.9 . . ? C9 C8 C7 122.1(9) . . ? C9 C8 H8A 119.0 . . ? C7 C8 H8A 119.0 . . ? C8 C9 C8 117.2(11) . 2_565 ? C8 C9 C10 121.4(5) . . ? C8 C9 C10 121.4(5) 2_565 . ? N3 C10 N3 111.4(13) . 2_565 ? N3 C10 C9 124.3(6) . . ? N3 C10 C9 124.3(6) 2_565 . ? N1 N1 N2 110.62(19) 8_655 . ? N1 N1 Cu1 124.42(8) 8_655 . ? N2 N1 Cu1 125.0(2) . . ? N1 N2 C5 103.8(3) . . ? C10 N3 N4 106.7(11) . . ? N4 N4 N3 107.6(7) 2_565 . ? C6 N5 C1 120.8(4) . . ? C6 N5 C1 120.8(4) . 2_565 ? C1 N5 C1 118.3(8) . 2_565 ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 -0.049 0.000 0.500 938 192 2 -0.026 0.500 0.000 264 87 _platon_squeeze_details ; This unit cell contains 16 methanol molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by squeeze/platon. ; _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.422 _refine_diff_density_min -0.758 _refine_diff_density_rms 0.094 #====END data_2 _database_code_depnum_ccdc_archive 'CCDC 894331' #TrackingRef '- CC-COM-07-2012-035456.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H59 Cu N13 O10 S3' _chemical_formula_weight 969.66 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Cmcm ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z-1/2' '-x, y, z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.337(13) _cell_length_b 38.203(16) _cell_length_c 7.079(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8475(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4088 _exptl_absorpt_coefficient_mu 0.735 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8097 _exptl_absorpt_correction_T_max 0.8670 _exptl_absorpt_process_details 'SADABS; Brucker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18284 _diffrn_reflns_av_R_equivalents 0.2998 _diffrn_reflns_av_sigmaI/netI 0.1674 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 0.84 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4182 _reflns_number_gt 2103 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Restraints have been applied to the displacement of coordinated DMSO molecules and the free-of-coordination tetrazole group to control the refinement. 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^)+(0.1418P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4182 _refine_ls_number_parameters 215 _refine_ls_number_restraints 76 _refine_ls_R_factor_all 0.1592 _refine_ls_R_factor_gt 0.1248 _refine_ls_wR_factor_ref 0.3027 _refine_ls_wR_factor_gt 0.2856 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.027 _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 0.0000 0.23816(3) 0.00033(13) 0.0323(4) Uani 1 2 d S . . S1 S 0.0000 0.31880(16) -0.2500 0.217(5) Uani 1 4 d SU . . S2 S 0.0000 0.15793(13) 0.2500 0.158(3) Uani 1 4 d SU . . O1 O 0.0000 0.2818(4) -0.2500 0.213(5) Uani 1 4 d SU . . O2 O 0.0000 0.1965(3) 0.2500 0.156(3) Uani 1 4 d SU . . N1 N 0.2407(3) 0.38296(18) 0.2500 0.047(2) Uani 1 2 d S . . N2 N 0.07694(18) 0.28138(13) 0.0922(7) 0.0399(14) Uani 1 1 d . . . N3 N 0.04445(17) 0.26216(13) 0.1570(6) 0.0341(13) Uani 1 1 d . . . N4 N 0.1922(5) 0.5488(3) 0.2500 0.146(5) Uani 1 2 d SDU . . N5 N 0.2043(5) 0.5836(3) 0.2500 0.154(5) Uani 1 2 d SDU . . N6 N 0.2484(5) 0.5870(3) 0.2500 0.158(5) Uani 1 2 d SDU . . N7 N 0.2638(4) 0.5531(3) 0.2500 0.150(5) Uani 1 2 d SDU . . C1 C 0.2367(4) 0.4196(2) 0.2500 0.041(2) Uani 1 2 d S . . C2 C 0.1977(4) 0.4358(2) 0.2500 0.050(3) Uani 1 2 d S . . H2 H 0.1727 0.4226 0.2500 0.060 Uiso 1 2 calc SR . . C3 C 0.1961(5) 0.4720(3) 0.2500 0.073(4) Uani 1 2 d S . . H3 H 0.1695 0.4827 0.2500 0.087 Uiso 1 2 calc SR . . C4 C 0.2317(4) 0.4930(2) 0.2500 0.047(3) Uani 1 2 d S . . C5 C 0.2702(5) 0.4772(3) 0.2500 0.079(4) Uani 1 2 d S . . H5 H 0.2950 0.4906 0.2500 0.095 Uiso 1 2 calc SR . . C6 C 0.2732(5) 0.4400(3) 0.2500 0.065(4) Uani 1 2 d S . . H6 H 0.2999 0.4294 0.2500 0.077 Uiso 1 2 calc SR . . C7 C 0.2298(5) 0.5296(3) 0.2500 0.135(5) Uani 1 2 d SDU . . C8 C 0.2042(3) 0.3612(2) 0.2500 0.046(3) Uani 1 2 d S . . C9 C 0.1855(3) 0.3503(2) 0.0807(12) 0.075(3) Uani 1 1 d . . . H9 H 0.1961 0.3584 -0.0341 0.090 Uiso 1 1 calc R . . C10 C 0.1517(3) 0.3279(2) 0.0841(10) 0.068(3) Uani 1 1 d . . . H10 H 0.1400 0.3203 -0.0294 0.082 Uiso 1 1 calc R . . C11 C 0.1347(3) 0.3164(2) 0.2500 0.037(2) Uani 1 2 d S . . C12 C 0.0957(3) 0.2930(2) 0.2500 0.033(2) Uani 1 2 d S . . C13 C 0.2814(3) 0.3660(2) 0.2500 0.046(3) Uani 1 2 d S . . C18 C 0.0477(6) 0.1404(4) 0.2500 0.161(4) Uani 1 2 d SU . . C19 C 0.0000 0.3399(4) -0.045(4) 0.221(5) Uani 1 2 d SU . . N8 N 0.45478(16) 0.28519(13) 0.3435(6) 0.0334(12) Uani 1 1 d . . . N9 N 0.42046(17) 0.30078(13) 0.4052(7) 0.0367(13) Uani 1 1 d . . . C14 C 0.3010(3) 0.3575(2) 0.4165(12) 0.079(3) Uani 1 1 d . . . H14 H 0.2886 0.3638 0.5309 0.094 Uiso 1 1 calc R . . C15 C 0.3392(3) 0.3395(3) 0.4137(11) 0.082(3) Uani 1 1 d . . . H15A H 0.3517 0.3333 0.5280 0.099 Uiso 1 1 calc R . . C16 C 0.3593(3) 0.3306(2) 0.2500 0.042(3) Uani 1 2 d S . . C17 C 0.3992(3) 0.3113(2) 0.2500 0.0285(19) 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 0.0470(7) 0.0374(6) 0.0124(5) -0.0043(4) 0.000 0.000 S1 0.377(12) 0.030(3) 0.245(9) 0.000 0.000 0.000 S2 0.130(5) 0.032(2) 0.312(9) 0.000 0.000 0.000 O1 0.373(13) 0.027(3) 0.240(10) 0.000 0.000 0.000 O2 0.128(5) 0.030(3) 0.309(9) 0.000 0.000 0.000 N1 0.052(5) 0.018(4) 0.070(6) 0.000 0.000 0.007(4) N2 0.059(4) 0.042(3) 0.019(2) -0.002(2) -0.001(3) -0.018(3) N3 0.046(3) 0.042(3) 0.014(2) -0.003(2) 0.010(2) 0.006(3) N4 0.345(14) 0.043(5) 0.051(5) 0.000 0.000 0.031(6) N5 0.353(15) 0.050(5) 0.058(5) 0.000 0.000 0.020(7) N6 0.356(15) 0.056(5) 0.062(5) 0.000 0.000 0.013(7) N7 0.350(14) 0.037(5) 0.063(5) 0.000 0.000 -0.004(6) C1 0.066(7) 0.028(5) 0.029(5) 0.000 0.000 -0.009(5) C2 0.065(8) 0.030(5) 0.057(6) 0.000 0.000 0.001(5) C3 0.128(13) 0.049(7) 0.041(6) 0.000 0.000 0.021(8) C4 0.091(9) 0.019(5) 0.032(5) 0.000 0.000 -0.011(5) C5 0.133(13) 0.034(7) 0.071(9) 0.000 0.000 -0.028(8) C6 0.100(10) 0.032(6) 0.062(7) 0.000 0.000 -0.020(6) C7 0.332(14) 0.031(5) 0.042(5) 0.000 0.000 0.013(6) C8 0.041(6) 0.040(6) 0.056(6) 0.000 0.000 -0.005(5) C9 0.090(7) 0.094(7) 0.040(4) 0.018(5) -0.006(5) -0.057(6) C10 0.074(6) 0.099(7) 0.031(4) -0.001(4) 0.006(4) -0.053(5) C11 0.044(6) 0.040(5) 0.027(4) 0.000 0.000 -0.009(5) C12 0.048(6) 0.027(5) 0.023(4) 0.000 0.000 -0.008(4) C13 0.048(6) 0.029(5) 0.060(7) 0.000 0.000 -0.002(5) C18 0.134(6) 0.038(4) 0.311(10) 0.000 0.000 0.007(3) C19 0.381(13) 0.036(5) 0.247(10) -0.005(4) 0.000 0.000 N8 0.045(3) 0.043(3) 0.012(2) 0.006(2) 0.012(2) 0.002(3) N9 0.042(3) 0.049(3) 0.019(3) -0.008(2) 0.004(3) 0.012(3) C14 0.078(6) 0.120(8) 0.038(4) -0.015(5) -0.016(5) 0.044(6) C15 0.093(7) 0.127(8) 0.027(4) -0.011(5) 0.010(5) 0.060(6) C16 0.071(8) 0.027(5) 0.028(4) 0.000 0.000 0.012(5) C17 0.034(5) 0.029(4) 0.022(4) 0.000 0.000 0.010(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 N3 2.003(5) 11 ? Cu1 N3 2.003(5) . ? Cu1 N8 2.009(5) 16_455 ? Cu1 N8 2.009(5) 6_554 ? Cu1 O2 2.378(8) . ? Cu1 O1 2.433(9) . ? S1 O1 1.413(15) . ? S1 C19 1.66(2) 10 ? S1 C19 1.66(2) . ? S2 O2 1.474(13) . ? S2 C18 1.639(19) . ? S2 C18 1.639(19) 11 ? O1 Cu1 2.433(9) 10 ? O2 Cu1 2.378(8) 10_556 ? N1 C1 1.407(11) . ? N1 C8 1.415(12) . ? N1 C13 1.431(13) . ? N2 N3 1.336(7) . ? N2 C12 1.338(7) . ? N3 N3 1.316(9) 10_556 ? N4 N5 1.383(9) . ? N4 C7 1.387(9) . ? N5 N6 1.388(9) . ? N6 N7 1.384(9) . ? N7 C7 1.392(9) . ? C1 C2 1.371(14) . ? C1 C6 1.382(15) . ? C2 C3 1.385(14) . ? C2 H2 0.9300 . ? C3 C4 1.373(17) . ? C3 H3 0.9300 . ? C4 C5 1.350(18) . ? C4 C7 1.401(14) . ? C5 C6 1.422(15) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.397(9) . ? C8 C9 1.397(9) 10_556 ? C9 C10 1.361(9) . ? C9 H9 0.9300 . ? C10 C11 1.363(8) . ? C10 H10 0.9300 . ? C11 C10 1.363(8) 10_556 ? C11 C12 1.514(12) . ? C12 N2 1.338(7) 10_556 ? C13 C14 1.367(9) . ? C13 C14 1.367(9) 10_556 ? N8 N9 1.305(6) . ? N8 N8 1.324(8) 10_556 ? N8 Cu1 2.009(5) 6 ? N9 C17 1.345(7) . ? C14 C15 1.382(11) . ? C14 H14 0.9300 . ? C15 C16 1.363(9) . ? C15 H15A 0.9300 . ? C16 C15 1.363(9) 10_556 ? C16 C17 1.452(12) . ? C17 N9 1.345(7) 10_556 ? 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 N3 Cu1 N3 88.1(3) 11 . ? N3 Cu1 N8 91.07(19) 11 16_455 ? N3 Cu1 N8 179.0(2) . 16_455 ? N3 Cu1 N8 179.0(2) 11 6_554 ? N3 Cu1 N8 91.07(19) . 6_554 ? N8 Cu1 N8 89.7(3) 16_455 6_554 ? N3 Cu1 O2 84.0(2) 11 . ? N3 Cu1 O2 84.0(2) . . ? N8 Cu1 O2 96.5(2) 16_455 . ? N8 Cu1 O2 96.5(2) 6_554 . ? N3 Cu1 O1 95.1(2) 11 . ? N3 Cu1 O1 95.1(2) . . ? N8 Cu1 O1 84.4(2) 16_455 . ? N8 Cu1 O1 84.4(2) 6_554 . ? O2 Cu1 O1 178.7(3) . . ? O1 S1 C19 119.1(7) . 10 ? O1 S1 C19 119.1(7) . . ? C19 S1 C19 121.9(13) 10 . ? O2 S2 C18 114.2(6) . . ? O2 S2 C18 114.2(6) . 11 ? C18 S2 C18 131.7(11) . 11 ? S1 O1 Cu1 133.3(2) . 10 ? S1 O1 Cu1 133.3(2) . . ? Cu1 O1 Cu1 93.5(5) 10 . ? S2 O2 Cu1 132.0(2) . 10_556 ? S2 O2 Cu1 132.0(2) . . ? Cu1 O2 Cu1 96.0(4) 10_556 . ? C1 N1 C8 120.9(9) . . ? C1 N1 C13 122.0(9) . . ? C8 N1 C13 117.1(7) . . ? N3 N2 C12 103.3(5) . . ? N3 N3 N2 110.1(3) 10_556 . ? N3 N3 Cu1 123.63(14) 10_556 . ? N2 N3 Cu1 126.2(3) . . ? N5 N4 C7 106.0(12) . . ? N4 N5 N6 111.2(10) . . ? N7 N6 N5 105.1(9) . . ? N6 N7 C7 109.6(9) . . ? C2 C1 C6 119.0(10) . . ? C2 C1 N1 121.8(9) . . ? C6 C1 N1 119.2(11) . . ? C1 C2 C3 118.7(11) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 123.7(13) . . ? C4 C3 H3 118.2 . . ? C2 C3 H3 118.2 . . ? C5 C4 C3 117.8(10) . . ? C5 C4 C7 118.9(12) . . ? C3 C4 C7 123.3(13) . . ? C4 C5 C6 120.2(12) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.6(13) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? N4 C7 N7 108.0(11) . . ? N4 C7 C4 124.2(12) . . ? N7 C7 C4 127.7(13) . . ? C9 C8 C9 118.2(9) . 10_556 ? C9 C8 N1 120.9(5) . . ? C9 C8 N1 120.9(5) 10_556 . ? C10 C9 C8 119.8(7) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 121.5(7) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C10 C11 C10 119.0(9) 10_556 . ? C10 C11 C12 120.5(5) 10_556 . ? C10 C11 C12 120.5(5) . . ? N2 C12 N2 113.2(8) . 10_556 ? N2 C12 C11 123.4(4) . . ? N2 C12 C11 123.4(4) 10_556 . ? C14 C13 C14 119.1(11) . 10_556 ? C14 C13 N1 120.4(5) . . ? C14 C13 N1 120.4(5) 10_556 . ? N9 N8 N8 109.6(3) . 10_556 ? N9 N8 Cu1 126.8(3) . 6 ? N8 N8 Cu1 123.54(13) 10_556 6 ? N8 N9 C17 105.7(5) . . ? C13 C14 C15 119.6(8) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 122.5(8) . . ? C16 C15 H15A 118.7 . . ? C14 C15 H15A 118.7 . . ? C15 C16 C15 116.5(10) 10_556 . ? C15 C16 C17 121.7(5) 10_556 . ? C15 C16 C17 121.7(5) . . ? N9 C17 N9 109.5(7) 10_556 . ? N9 C17 C16 125.3(4) 10_556 . ? N9 C17 C16 125.3(4) . . ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 0.000 0.000 -0.015 824 349 2 0.000 0.500 0.230 757 319 3 0.250 0.250 0.703 283 90 4 0.250 0.750 0.221 283 89 5 0.500 0.500 0.705 824 349 6 0.500 0.000 0.027 757 319 7 0.750 0.250 0.221 283 89 8 0.750 0.750 0.703 283 90 _platon_squeeze_details ; This unit cell contains around 56 methanol and 16 DMSO molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by squeeze/platon. ; _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 3.748 _refine_diff_density_min -1.708 _refine_diff_density_rms 0.161 #====END data_3 _database_code_depnum_ccdc_archive 'CCDC 894332' #TrackingRef '- CC-COM-07-2012-035456.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H43 Cu N13 O6 S3' _chemical_formula_weight 841.49 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Cmcm ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' 'x+1/2, -y+1/2, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 31.552(6) _cell_length_b 37.319(7) _cell_length_c 7.1146(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8378(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour dark-green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3512 _exptl_absorpt_coefficient_mu 0.726 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8117 _exptl_absorpt_correction_T_max 0.8685 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16379 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0672 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 0.85 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4127 _reflns_number_gt 2932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1697P)^2^+1.5779P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4127 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.2241 _refine_ls_wR_factor_gt 0.2084 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _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 Cu1 Cu 0.0000 0.256125(16) 0.00000(5) 0.0388(3) Uani 1 2 d S . . C1 C 0.2634(4) 0.5334(2) 0.2500 0.117(3) Uani 1 2 d S . . C2 C 0.2607(3) 0.49458(16) 0.2500 0.086(2) Uani 1 2 d S . . C3 C 0.2227(3) 0.47699(19) 0.2500 0.098(2) Uani 1 2 d S . . H3A H 0.1977 0.4903 0.2500 0.118 Uiso 1 2 calc SR . . C4 C 0.2963(3) 0.47409(19) 0.2500 0.095(2) Uani 1 2 d S . . H4A H 0.3226 0.4853 0.2500 0.114 Uiso 1 2 calc SR . . C5 C 0.2203(2) 0.44001(16) 0.2500 0.0811(18) Uani 1 2 d S . . H5A H 0.1940 0.4288 0.2500 0.097 Uiso 1 2 calc SR . . C6 C 0.29453(19) 0.43690(16) 0.2500 0.0790(17) Uani 1 2 d S . . H6A H 0.3196 0.4238 0.2500 0.095 Uiso 1 2 calc SR . . C7 C 0.25750(16) 0.41946(15) 0.2500 0.0639(14) Uani 1 2 d S . . C8 C 0.21520(14) 0.36411(14) 0.2500 0.0657(14) Uani 1 2 d S . . C9 C 0.19655(15) 0.35447(17) 0.0931(8) 0.123(2) Uani 1 1 d . . . H9A H 0.2079 0.3622 -0.0205 0.147 Uiso 1 1 calc R . . C10 C 0.16007(14) 0.33293(16) 0.0906(7) 0.1159(19) Uani 1 1 d . . . H10 H 0.1504 0.3232 -0.0218 0.139 Uiso 1 1 calc R . . C11 C 0.13953(13) 0.32658(13) 0.2500 0.0551(11) Uani 1 2 d S . . C12 C 0.09968(12) 0.30614(12) 0.2500 0.0455(10) Uani 1 2 d S . . C13 C 0.29234(13) 0.36103(14) 0.2500 0.0640(14) Uani 1 2 d S . . C14 C 0.30894(15) 0.34984(15) 0.0900(8) 0.1129(18) Uani 1 1 d . . . H14 H 0.2966 0.3566 -0.0234 0.135 Uiso 1 1 calc R . . C15 C 0.34519(14) 0.32770(15) 0.0898(7) 0.1081(17) Uani 1 1 d . . . H15 H 0.3560 0.3194 -0.0237 0.130 Uiso 1 1 calc R . . C16 C 0.40230(12) 0.29611(12) 0.2500 0.0472(10) Uani 1 2 d S . . C17 C 0.36408(12) 0.31854(13) 0.2500 0.0562(12) Uani 1 2 d S . . C18 C 0.0000 0.3387(2) -0.2500 0.130(4) Uani 1 4 d S . . C19 C 0.0000 0.17488(19) 0.2500 0.146(5) Uani 1 4 d S . . N1 N 0.2254(4) 0.5551(2) 0.2500 0.168(5) Uani 1 2 d S . . N2 N 0.2452(6) 0.5856(5) 0.2500 0.177(7) Uani 1 2 d S . . N3 N 0.2925(4) 0.5539(2) 0.2500 0.162(4) Uani 1 2 d S . . N4 N 0.2795(6) 0.5878(5) 0.2500 0.213(10) Uani 1 2 d S . . N5 N 0.25533(11) 0.38253(12) 0.2500 0.0711(14) Uani 1 2 d S . . N6 N 0.04470(6) 0.27952(7) 0.1577(3) 0.0424(6) Uani 1 1 d . . . N7 N 0.07898(7) 0.29608(7) 0.0954(3) 0.0497(7) Uani 1 1 d . . . N8 N 0.45540(7) 0.26748(7) 0.1581(3) 0.0432(6) Uani 1 1 d . . . N9 N 0.42228(7) 0.28532(7) 0.0949(4) 0.0499(7) Uani 1 1 d . . . O1A O 0.0000 0.30008(11) -0.2500 0.0569(11) Uani 1 4 d S . . O2A O 0.0000 0.21200(12) 0.2500 0.0631(12) Uani 1 4 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 0.0202(3) 0.0705(5) 0.0257(4) -0.00300(19) 0.000 0.000 C1 0.218(10) 0.076(5) 0.059(4) 0.000 0.000 -0.011(6) C2 0.141(7) 0.051(3) 0.066(5) 0.000 0.000 -0.006(4) C3 0.126(6) 0.072(4) 0.096(5) 0.000 0.000 0.015(4) C4 0.121(6) 0.074(4) 0.090(5) 0.000 0.000 -0.028(4) C5 0.073(4) 0.065(3) 0.106(5) 0.000 0.000 0.008(3) C6 0.068(3) 0.064(3) 0.106(5) 0.000 0.000 -0.009(3) C7 0.049(3) 0.067(3) 0.076(4) 0.000 0.000 -0.006(2) C8 0.029(2) 0.068(3) 0.100(4) 0.000 0.000 -0.002(2) C9 0.083(3) 0.201(6) 0.084(3) 0.003(4) 0.010(3) -0.083(4) C10 0.076(3) 0.197(6) 0.075(3) -0.010(3) 0.011(2) -0.075(3) C11 0.030(2) 0.075(3) 0.061(3) 0.000 0.000 -0.007(2) C12 0.0257(19) 0.068(3) 0.043(2) 0.000 0.000 -0.0066(19) C13 0.028(2) 0.063(3) 0.102(4) 0.000 0.000 0.000(2) C14 0.087(3) 0.166(5) 0.086(3) 0.003(3) -0.016(3) 0.075(3) C15 0.087(3) 0.170(5) 0.068(3) -0.002(3) -0.007(2) 0.077(3) C16 0.031(2) 0.069(3) 0.042(2) 0.000 0.000 0.006(2) C17 0.028(2) 0.079(3) 0.063(3) 0.000 0.000 0.010(2) C18 0.120(8) 0.041(4) 0.228(13) 0.000 0.000 0.000 C19 0.171(11) 0.024(3) 0.242(15) 0.000 0.000 0.000 N1 0.339(16) 0.065(4) 0.099(5) 0.000 0.000 0.030(7) N2 0.36(2) 0.085(8) 0.087(6) 0.000 0.000 -0.017(13) N3 0.316(13) 0.079(5) 0.092(5) 0.000 0.000 -0.069(7) N4 0.48(3) 0.073(6) 0.091(6) 0.000 0.000 -0.052(16) N5 0.033(2) 0.062(3) 0.118(4) 0.000 0.000 -0.0011(18) N6 0.0267(10) 0.0739(15) 0.0267(11) -0.0062(11) 0.0064(9) -0.0040(11) N7 0.0292(12) 0.0777(17) 0.0422(15) 0.0032(12) 0.0069(10) -0.0100(12) N8 0.0273(11) 0.0744(15) 0.0280(11) -0.0021(11) -0.0039(9) 0.0048(11) N9 0.0287(12) 0.0748(17) 0.0463(15) -0.0019(13) -0.0055(11) 0.0118(12) O1A 0.064(3) 0.051(2) 0.055(3) 0.000 0.000 0.000 O2A 0.074(3) 0.066(3) 0.050(3) 0.000 0.000 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 N6 2.002(2) . ? Cu1 N6 2.002(2) 12 ? Cu1 N8 2.006(2) 8_455 ? Cu1 N8 2.006(2) 13 ? Cu1 O1A 2.420(3) . ? Cu1 O2A 2.424(3) . ? C1 N3 1.196(14) . ? C1 N1 1.445(16) . ? C1 C2 1.453(10) . ? C2 C4 1.359(10) . ? C2 C3 1.367(11) . ? C3 C5 1.382(9) . ? C3 H3A 0.9300 . ? C4 C6 1.389(9) . ? C4 H4A 0.9300 . ? C5 C7 1.403(7) . ? C5 H5A 0.9300 . ? C6 C7 1.338(7) . ? C6 H6A 0.9300 . ? C7 N5 1.380(8) . ? C8 C9 1.312(5) . ? C8 C9 1.312(5) 10_556 ? C8 N5 1.441(5) . ? C9 C10 1.404(5) . ? C9 H9A 0.9300 . ? C10 C11 1.328(5) . ? C10 H10 0.9300 . ? C11 C10 1.328(5) 10_556 ? C11 C12 1.470(5) . ? C12 N7 1.333(3) . ? C12 N7 1.333(3) 10_556 ? C13 C14 1.321(5) 10_556 ? C13 C14 1.321(5) . ? C13 N5 1.417(6) . ? C14 C15 1.411(5) . ? C14 H14 0.9300 . ? C15 C17 1.331(5) . ? C15 H15 0.9300 . ? C16 N9 1.333(3) 10_556 ? C16 N9 1.333(3) . ? C16 C17 1.468(5) . ? C17 C15 1.331(5) 10_556 ? C18 O1A 1.441(9) . ? C19 O2A 1.385(8) . ? N1 N2 1.296(19) . ? N2 N4 1.09(3) . ? N3 N4 1.33(2) . ? N6 N6 1.314(4) 10_556 ? N6 N7 1.322(3) . ? N8 N8 1.308(4) 10_556 ? N8 N9 1.318(3) . ? N8 Cu1 2.006(2) 13 ? O1A Cu1 2.420(3) 10 ? O2A Cu1 2.424(3) 10_556 ? 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 N6 Cu1 N6 89.55(12) . 12 ? N6 Cu1 N8 179.75(10) . 8_455 ? N6 Cu1 N8 90.66(9) 12 8_455 ? N6 Cu1 N8 90.66(9) . 13 ? N6 Cu1 N8 179.75(10) 12 13 ? N8 Cu1 N8 89.13(12) 8_455 13 ? N6 Cu1 O1A 96.67(9) . . ? N6 Cu1 O1A 96.67(9) 12 . ? N8 Cu1 O1A 83.43(9) 8_455 . ? N8 Cu1 O1A 83.43(9) 13 . ? N6 Cu1 O2A 83.41(9) . . ? N6 Cu1 O2A 83.41(9) 12 . ? N8 Cu1 O2A 96.49(9) 8_455 . ? N8 Cu1 O2A 96.49(9) 13 . ? O1A Cu1 O2A 179.89(11) . . ? N3 C1 N1 106.2(9) . . ? N3 C1 C2 133.1(13) . . ? N1 C1 C2 120.8(11) . . ? C4 C2 C3 117.1(6) . . ? C4 C2 C1 120.9(9) . . ? C3 C2 C1 122.0(9) . . ? C2 C3 C5 121.8(7) . . ? C2 C3 H3A 119.1 . . ? C5 C3 H3A 119.1 . . ? C2 C4 C6 121.9(6) . . ? C2 C4 H4A 119.0 . . ? C6 C4 H4A 119.0 . . ? C3 C5 C7 120.0(6) . . ? C3 C5 H5A 120.0 . . ? C7 C5 H5A 120.0 . . ? C7 C6 C4 121.4(6) . . ? C7 C6 H6A 119.3 . . ? C4 C6 H6A 119.3 . . ? C6 C7 N5 122.0(5) . . ? C6 C7 C5 117.7(5) . . ? N5 C7 C5 120.3(5) . . ? C9 C8 C9 116.6(5) . 10_556 ? C9 C8 N5 121.7(3) . . ? C9 C8 N5 121.7(3) 10_556 . ? C8 C9 C10 122.4(5) . . ? C8 C9 H9A 118.8 . . ? C10 C9 H9A 118.8 . . ? C11 C10 C9 119.4(5) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C10 117.3(5) 10_556 . ? C10 C11 C12 120.7(2) 10_556 . ? C10 C11 C12 120.7(2) . . ? N7 C12 N7 111.2(3) . 10_556 ? N7 C12 C11 124.40(17) . . ? N7 C12 C11 124.40(17) 10_556 . ? C14 C13 C14 119.0(5) 10_556 . ? C14 C13 N5 120.4(2) 10_556 . ? C14 C13 N5 120.4(2) . . ? C13 C14 C15 120.5(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C17 C15 C14 120.8(4) . . ? C17 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? N9 C16 N9 111.7(3) 10_556 . ? N9 C16 C17 124.10(17) 10_556 . ? N9 C16 C17 124.10(17) . . ? C15 C17 C15 117.8(5) . 10_556 ? C15 C17 C16 121.0(2) . . ? C15 C17 C16 121.0(2) 10_556 . ? N2 N1 C1 95.4(13) . . ? N4 N2 N1 123(3) . . ? C1 N3 N4 111.7(16) . . ? N2 N4 N3 104(2) . . ? C7 N5 C13 121.7(4) . . ? C7 N5 C8 121.3(4) . . ? C13 N5 C8 117.0(4) . . ? N6 N6 N7 109.57(14) 10_556 . ? N6 N6 Cu1 124.07(6) 10_556 . ? N7 N6 Cu1 126.33(17) . . ? N6 N7 C12 104.8(2) . . ? N8 N8 N9 109.94(14) 10_556 . ? N8 N8 Cu1 124.12(6) 10_556 13 ? N9 N8 Cu1 125.94(18) . 13 ? N8 N9 C16 104.2(2) . . ? C18 O1A Cu1 132.69(7) . 10 ? C18 O1A Cu1 132.69(7) . . ? Cu1 O1A Cu1 94.63(15) 10 . ? C19 O2A Cu1 132.80(8) . . ? C19 O2A Cu1 132.80(8) . 10_556 ? Cu1 O2A Cu1 94.41(16) . 10_556 ? 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 N3 C1 C2 C4 0.0 . . . . ? N1 C1 C2 C4 180.0 . . . . ? N3 C1 C2 C3 180.0 . . . . ? N1 C1 C2 C3 0.0 . . . . ? C4 C2 C3 C5 0.0 . . . . ? C1 C2 C3 C5 180.0 . . . . ? C3 C2 C4 C6 0.0 . . . . ? C1 C2 C4 C6 180.0 . . . . ? C2 C3 C5 C7 0.0 . . . . ? C2 C4 C6 C7 0.0 . . . . ? C4 C6 C7 N5 180.0 . . . . ? C4 C6 C7 C5 0.0 . . . . ? C3 C5 C7 C6 0.0 . . . . ? C3 C5 C7 N5 180.0 . . . . ? C9 C8 C9 C10 -4.2(11) 10_556 . . . ? N5 C8 C9 C10 172.4(5) . . . . ? C8 C9 C10 C11 11.0(10) . . . . ? C9 C10 C11 C10 -17.1(11) . . . 10_556 ? C9 C10 C11 C12 175.9(5) . . . . ? C10 C11 C12 N7 -174.2(5) 10_556 . . . ? C10 C11 C12 N7 -7.7(7) . . . . ? C10 C11 C12 N7 7.7(7) 10_556 . . 10_556 ? C10 C11 C12 N7 174.2(5) . . . 10_556 ? C14 C13 C14 C15 -3.2(11) 10_556 . . . ? N5 C13 C14 C15 -178.4(5) . . . . ? C13 C14 C15 C17 -2.0(9) . . . . ? C14 C15 C17 C15 7.0(11) . . . 10_556 ? C14 C15 C17 C16 -178.8(5) . . . . ? N9 C16 C17 C15 -178.5(5) 10_556 . . . ? N9 C16 C17 C15 4.5(8) . . . . ? N9 C16 C17 C15 -4.5(8) 10_556 . . 10_556 ? N9 C16 C17 C15 178.5(5) . . . 10_556 ? N3 C1 N1 N2 0.0 . . . . ? C2 C1 N1 N2 180.0 . . . . ? C1 N1 N2 N4 0.0 . . . . ? N1 C1 N3 N4 0.0 . . . . ? C2 C1 N3 N4 180.0 . . . . ? N1 N2 N4 N3 0.0 . . . . ? C1 N3 N4 N2 0.0 . . . . ? C6 C7 N5 C13 0.0 . . . . ? C5 C7 N5 C13 180.0 . . . . ? C6 C7 N5 C8 180.0 . . . . ? C5 C7 N5 C8 0.0 . . . . ? C14 C13 N5 C7 92.4(5) 10_556 . . . ? C14 C13 N5 C7 -92.4(5) . . . . ? C14 C13 N5 C8 -87.6(5) 10_556 . . . ? C14 C13 N5 C8 87.6(5) . . . . ? C9 C8 N5 C7 91.8(5) . . . . ? C9 C8 N5 C7 -91.8(5) 10_556 . . . ? C9 C8 N5 C13 -88.2(5) . . . . ? C9 C8 N5 C13 88.2(5) 10_556 . . . ? N6 Cu1 N6 N6 47.86(11) 12 . . 10_556 ? N8 Cu1 N6 N6 -101(38) 8_455 . . 10_556 ? N8 Cu1 N6 N6 -132.02(8) 13 . . 10_556 ? O1A Cu1 N6 N6 144.52(7) . . . 10_556 ? O2A Cu1 N6 N6 -35.56(7) . . . 10_556 ? N6 Cu1 N6 N7 -134.49(19) 12 . . . ? N8 Cu1 N6 N7 76(32) 8_455 . . . ? N8 Cu1 N6 N7 45.6(2) 13 . . . ? O1A Cu1 N6 N7 -37.8(2) . . . . ? O2A Cu1 N6 N7 142.1(2) . . . . ? N6 N6 N7 C12 -0.1(3) 10_556 . . . ? Cu1 N6 N7 C12 -178.0(2) . . . . ? N7 C12 N7 N6 0.1(5) 10_556 . . . ? C11 C12 N7 N6 -178.2(4) . . . . ? N8 N8 N9 C16 0.0(3) 10_556 . . . ? Cu1 N8 N9 C16 -179.5(2) 13 . . . ? N9 C16 N9 N8 -0.1(5) 10_556 . . . ? C17 C16 N9 N8 177.3(4) . . . . ? N6 Cu1 O1A C18 -45.17(6) . . . . ? N6 Cu1 O1A C18 45.17(6) 12 . . . ? N8 Cu1 O1A C18 135.06(6) 8_455 . . . ? N8 Cu1 O1A C18 -135.06(6) 13 . . . ? O2A Cu1 O1A C18 180(100) . . . . ? N6 Cu1 O1A Cu1 134.83(6) . . . 10 ? N6 Cu1 O1A Cu1 -134.83(6) 12 . . 10 ? N8 Cu1 O1A Cu1 -44.94(6) 8_455 . . 10 ? N8 Cu1 O1A Cu1 44.94(6) 13 . . 10 ? O2A Cu1 O1A Cu1 0(100) . . . 10 ? N6 Cu1 O2A C19 -134.84(6) . . . . ? N6 Cu1 O2A C19 134.84(6) 12 . . . ? N8 Cu1 O2A C19 44.93(6) 8_455 . . . ? N8 Cu1 O2A C19 -44.93(6) 13 . . . ? O1A Cu1 O2A C19 0(100) . . . . ? N6 Cu1 O2A Cu1 45.16(6) . . . 10_556 ? N6 Cu1 O2A Cu1 -45.16(6) 12 . . 10_556 ? N8 Cu1 O2A Cu1 -135.07(6) 8_455 . . 10_556 ? N8 Cu1 O2A Cu1 135.07(6) 13 . . 10_556 ? O1A Cu1 O2A Cu1 180(100) . . . 10_556 ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 0.000 0.000 -0.015 877 192 2 0.000 0.500 0.188 912 206 3 0.250 0.250 0.213 257 90 4 0.250 0.750 0.210 257 90 5 0.500 0.000 0.004 911 206 6 0.500 0.500 0.727 877 192 7 0.750 0.250 0.211 257 90 8 0.750 0.750 0.213 257 90 _platon_squeeze_details ; This unit cell contains 16 methanol and 24 DMSO molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by squeeze/platon. ; _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.315 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.091 #====END data_3a _database_code_depnum_ccdc_archive 'CCDC 894333' #TrackingRef '- CC-COM-07-2012-035456.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H45 Cu N13 O8' _chemical_formula_weight 767.32 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pmma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x+1/2, -y, -z' '-x, y, -z' '-x, -y, -z' 'x-1/2, y, -z' '-x-1/2, y, z' 'x, -y, z' _cell_length_a 7.067(2) _cell_length_b 15.675(5) _cell_length_c 18.811(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2083.8(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour dark-green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 806 _exptl_absorpt_coefficient_mu 0.581 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8449 _exptl_absorpt_correction_T_max 0.9442 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11588 _diffrn_reflns_av_R_equivalents 0.0773 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2094 _reflns_number_gt 1307 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; One restraint has been applied to the modeling of the free-of-coordination tetrazole group. 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^)+(0.0842P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2094 _refine_ls_number_parameters 107 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_restrained_S_all 0.874 _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 0.0000 0.0000 0.0556(3) Uani 1 4 d S . . N1 N 0.4074(3) 0.15559(13) 0.08242(13) 0.0640(6) Uani 1 1 d . . . N2 N 0.3433(3) 0.08890(12) 0.04673(11) 0.0568(6) Uani 1 1 d . . . N3 N 0.2500 0.5360(16) 0.6701(3) 0.305(18) Uani 1 2 d SD . . N4 N 0.2500 0.5687(7) 0.6036(3) 0.229(6) Uani 1 2 d SD . . N5 N 0.2500 0.5000 0.2663(3) 0.0774(16) Uani 1 4 d S . . C1 C 0.2500 0.1957(2) 0.1040(2) 0.0626(11) Uani 1 2 d S . . C2 C 0.2500 0.2745(2) 0.1470(2) 0.0646(11) Uani 1 2 d S . . C3 C 0.0900(6) 0.3106(3) 0.1686(3) 0.1391(19) Uani 1 1 d . . . H3 H -0.0249 0.2855 0.1566 0.167 Uiso 1 1 calc R . . C4 C 0.0909(7) 0.3848(3) 0.2085(3) 0.1390(19) Uani 1 1 d . . . H4 H -0.0236 0.4085 0.2228 0.167 Uiso 1 1 calc R . . C5 C 0.2500 0.4226(2) 0.2267(2) 0.0710(12) Uani 1 2 d S . . C6 C 0.2500 0.5000 0.3386(3) 0.0638(16) Uani 1 4 d S . . C7 C 0.2500 0.5763(3) 0.3783(3) 0.0890(15) Uani 1 2 d S . . H7 H 0.2500 0.6284 0.3547 0.107 Uiso 1 2 calc SR . . C8 C 0.2500 0.5748(4) 0.4520(3) 0.1001(17) Uani 1 2 d S . . H8 H 0.2500 0.6263 0.4766 0.120 Uiso 1 2 calc SR . . C9 C 0.2500 0.5000 0.4896(4) 0.099(3) Uani 1 4 d S . . C10 C 0.2500 0.5000 0.5620(6) 0.128(4) Uani 1 4 d S . . O1 O 0.2500 0.0000 -0.0922(3) 0.0937(15) Uani 1 4 d S . . C11 C 0.2500 0.0000 -0.1568(6) 0.260(11) Uani 1 4 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 0.0372(3) 0.0294(3) 0.1002(6) 0.000 0.0028(4) 0.000 N1 0.0526(13) 0.0404(12) 0.0990(18) -0.0105(12) -0.0015(13) -0.0084(11) N2 0.0404(10) 0.0342(10) 0.0958(17) -0.0089(11) -0.0010(11) -0.0044(9) N3 0.097(3) 0.71(5) 0.109(4) -0.100(15) 0.000 0.000 N4 0.105(4) 0.520(17) 0.064(4) -0.067(7) 0.000 0.000 N5 0.140(5) 0.038(2) 0.055(3) 0.000 0.000 0.000 C1 0.062(2) 0.0369(19) 0.089(3) -0.0009(19) 0.000 0.000 C2 0.077(3) 0.0323(18) 0.084(3) -0.0066(19) 0.000 0.000 C3 0.088(3) 0.100(3) 0.230(5) -0.095(3) 0.009(3) -0.008(3) C4 0.097(3) 0.105(3) 0.215(5) -0.088(3) 0.018(3) 0.007(3) C5 0.100(4) 0.0312(19) 0.081(3) -0.0006(19) 0.000 0.000 C6 0.072(4) 0.046(3) 0.073(5) 0.000 0.000 0.000 C7 0.110(4) 0.075(3) 0.082(4) -0.007(3) 0.000 0.000 C8 0.107(4) 0.113(5) 0.080(4) -0.029(4) 0.000 0.000 C9 0.053(4) 0.187(11) 0.059(7) 0.000 0.000 0.000 C10 0.055(4) 0.271(15) 0.058(7) 0.000 0.000 0.000 O1 0.052(2) 0.136(4) 0.093(4) 0.000 0.000 0.000 C11 0.115(8) 0.58(3) 0.088(8) 0.000 0.000 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 N2 1.985(2) 8 ? Cu1 N2 1.985(2) . ? Cu1 N2 1.985(2) 4_655 ? Cu1 N2 1.985(2) 5_655 ? N1 N2 1.322(3) . ? N1 C1 1.341(3) . ? N2 N2 1.318(4) 7_655 ? N3 N3 1.13(5) 2_565 ? N3 N4 1.352(9) . ? N4 C10 1.331(9) . ? N5 C6 1.360(7) . ? N5 C5 1.424(5) . ? N5 C5 1.424(5) 2_565 ? C1 N1 1.341(3) 7_655 ? C1 C2 1.475(5) . ? C2 C3 1.328(4) 7_655 ? C2 C3 1.328(4) . ? C3 C4 1.385(5) . ? C3 H3 0.9300 . ? C4 C5 1.316(5) . ? C4 H4 0.9300 . ? C5 C4 1.316(5) 7_655 ? C6 C7 1.410(6) 2_565 ? C6 C7 1.410(6) . ? C7 C8 1.386(7) . ? C7 H7 0.9300 . ? C8 C9 1.370(6) . ? C8 H8 0.9300 . ? C9 C10 1.363(12) . ? C9 C8 1.370(6) 2_565 ? C10 N4 1.331(9) 2_565 ? O1 C11 1.216(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N2 89.16(11) 8 . ? N2 Cu1 N2 180.00(16) 8 4_655 ? N2 Cu1 N2 90.84(11) . 4_655 ? N2 Cu1 N2 90.84(11) 8 5_655 ? N2 Cu1 N2 180.00(16) . 5_655 ? N2 Cu1 N2 89.16(11) 4_655 5_655 ? N2 N1 C1 103.9(2) . . ? N2 N2 N1 110.03(13) 7_655 . ? N2 N2 Cu1 123.91(6) 7_655 . ? N1 N2 Cu1 126.06(16) . . ? N3 N3 N4 112.3(10) 2_565 . ? C10 N4 N3 103.7(11) . . ? C6 N5 C5 121.5(2) . . ? C6 N5 C5 121.5(2) . 2_565 ? C5 N5 C5 116.9(5) . 2_565 ? N1 C1 N1 112.1(3) 7_655 . ? N1 C1 C2 123.96(16) 7_655 . ? N1 C1 C2 123.96(16) . . ? C3 C2 C3 116.7(4) 7_655 . ? C3 C2 C1 121.6(2) 7_655 . ? C3 C2 C1 121.6(2) . . ? C2 C3 C4 121.4(4) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 121.5(4) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C4 117.4(5) . 7_655 ? C4 C5 N5 121.3(2) . . ? C4 C5 N5 121.3(2) 7_655 . ? N5 C6 C7 122.0(3) . 2_565 ? N5 C6 C7 122.0(3) . . ? C7 C6 C7 116.1(6) 2_565 . ? C8 C7 C6 121.0(5) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C9 C8 C7 122.1(6) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C10 C9 C8 121.1(4) . . ? C10 C9 C8 121.1(4) . 2_565 ? C8 C9 C8 117.8(7) . 2_565 ? N4 C10 N4 108.0(10) . 2_565 ? N4 C10 C9 126.0(5) . . ? N4 C10 C9 126.0(5) 2_565 . ? 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 C1 N1 N2 N2 0.1(3) . . . 7_655 ? C1 N1 N2 Cu1 -179.4(2) . . . . ? N2 Cu1 N2 N2 -48.51(10) 8 . . 7_655 ? N2 Cu1 N2 N2 131.49(10) 4_655 . . 7_655 ? N2 Cu1 N2 N2 100(33) 5_655 . . 7_655 ? N2 Cu1 N2 N1 130.95(18) 8 . . . ? N2 Cu1 N2 N1 -49.05(18) 4_655 . . . ? N2 Cu1 N2 N1 -81(33) 5_655 . . . ? N3 N3 N4 C10 0.000(6) 2_565 . . . ? N2 N1 C1 N1 -0.2(4) . . . 7_655 ? N2 N1 C1 C2 179.5(3) . . . . ? N1 C1 C2 C3 178.3(4) 7_655 . . 7_655 ? N1 C1 C2 C3 -1.3(7) . . . 7_655 ? N1 C1 C2 C3 1.3(7) 7_655 . . . ? N1 C1 C2 C3 -178.3(4) . . . . ? C3 C2 C3 C4 3.3(10) 7_655 . . . ? C1 C2 C3 C4 -179.6(4) . . . . ? C2 C3 C4 C5 0.0(9) . . . . ? C3 C4 C5 C4 -3.4(10) . . . 7_655 ? C3 C4 C5 N5 178.5(4) . . . . ? C6 N5 C5 C4 89.1(5) . . . . ? C5 N5 C5 C4 -90.9(5) 2_565 . . . ? C6 N5 C5 C4 -89.1(5) . . . 7_655 ? C5 N5 C5 C4 90.9(5) 2_565 . . 7_655 ? C5 N5 C6 C7 0.000(1) . . . 2_565 ? C5 N5 C6 C7 180.000(1) 2_565 . . 2_565 ? C5 N5 C6 C7 180.000(1) . . . . ? C5 N5 C6 C7 0.000(1) 2_565 . . . ? N5 C6 C7 C8 180.000(1) . . . . ? C7 C6 C7 C8 0.000(2) 2_565 . . . ? C6 C7 C8 C9 0.000(2) . . . . ? C7 C8 C9 C10 180.000(2) . . . . ? C7 C8 C9 C8 0.000(3) . . . 2_565 ? N3 N4 C10 N4 0.000(4) . . . 2_565 ? N3 N4 C10 C9 180.000(3) . . . . ? C8 C9 C10 N4 0.000(3) . . . . ? C8 C9 C10 N4 180.000(3) 2_565 . . . ? C8 C9 C10 N4 180.000(3) . . . 2_565 ? C8 C9 C10 N4 0.000(3) 2_565 . . 2_565 ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 -0.043 0.000 0.500 867 206 2 -0.026 0.500 0.000 277 49 _platon_squeeze_details ; This unit cell contains 14 methanol molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by squeeze/platon. ; _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.724 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.069 #====END