# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Jing-Yun Wu' _publ_contact_author_email jyunwu@ncnu.edu.tw _publ_section_title ; Synthesis, characterization and structural transformation of a discrete tetragonal metalloprism ; _publ_author_name 'Jing-Yun Wu' # Attachment '- cpd 1_revised.cif' data_cpd1 _database_code_depnum_ccdc_archive 'CCDC 796950' #TrackingRef '- cpd 1_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H56 Cu2 N20 O24' _chemical_formula_weight 1424.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz '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, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.1789(13) _cell_length_b 12.8654(9) _cell_length_c 23.3516(16) _cell_angle_alpha 90.00 _cell_angle_beta 114.808(2) _cell_angle_gamma 90.00 _cell_volume 5775.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4228 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 24.97 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2936 _exptl_absorpt_coefficient_mu 0.839 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6675 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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 '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 18090 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.08 _reflns_number_total 5036 _reflns_number_gt 3422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0279P)^2^+11.4180P] 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 5036 _refine_ls_number_parameters 456 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.96813(18) 0.7254(3) 0.46613(16) 0.0315(9) Uani 1 1 d . . . H1A H 0.9912 0.6591 0.4806 0.038 Uiso 1 1 calc R . . H1B H 1.0014 0.7728 0.4617 0.038 Uiso 1 1 calc R . . C2 C 1.00217(16) 0.8154(3) 0.56939(16) 0.0261(8) Uani 1 1 d . . . H2A H 1.0312 0.8568 0.5553 0.031 Uiso 1 1 calc R . . H2B H 1.0309 0.7610 0.5967 0.031 Uiso 1 1 calc R . . C3 C 0.84436(18) 0.6735(3) 0.39849(17) 0.0261(8) Uani 1 1 d . . . H3 H 0.8412 0.6514 0.4351 0.031 Uiso 1 1 calc R . . C4 C 0.90766(17) 0.7110(2) 0.40318(16) 0.0241(8) Uani 1 1 d . . . C5 C 0.91258(19) 0.7367(3) 0.34815(17) 0.0327(9) Uani 1 1 d . . . H5 H 0.9549 0.7583 0.3491 0.039 Uiso 1 1 calc R . . C6 C 0.8550(2) 0.7303(3) 0.29179(18) 0.0375(10) Uani 1 1 d . . . H6 H 0.8578 0.7479 0.2543 0.045 Uiso 1 1 calc R . . C7 C 0.79268(19) 0.6973(3) 0.29140(17) 0.0308(9) Uani 1 1 d . . . H7 H 0.7532 0.6958 0.2534 0.037 Uiso 1 1 calc R . . C8 C 0.91771(17) 0.8549(3) 0.61754(15) 0.0256(8) Uani 1 1 d . . . H8 H 0.8973 0.7904 0.6034 0.031 Uiso 1 1 calc R . . C9 C 0.97453(16) 0.8832(3) 0.60622(15) 0.0233(8) Uani 1 1 d . . . C10 C 1.00555(18) 0.9784(3) 0.62900(16) 0.0297(9) Uani 1 1 d . . . H10 H 1.0434 1.0004 0.6217 0.036 Uiso 1 1 calc R . . C11 C 0.9799(2) 1.0399(3) 0.66245(18) 0.0374(10) Uani 1 1 d . . . H11 H 1.0013 1.1027 0.6795 0.045 Uiso 1 1 calc R . . C12 C 0.92210(19) 1.0076(3) 0.67049(17) 0.0315(9) Uani 1 1 d . . . H12 H 0.9043 1.0505 0.6922 0.038 Uiso 1 1 calc R . . C13 C 0.67141(19) 1.0392(3) 0.34599(17) 0.0344(9) Uani 1 1 d . . . H13A H 0.7140 1.0602 0.3432 0.041 Uiso 1 1 calc R . . H13B H 0.6374 1.0941 0.3279 0.041 Uiso 1 1 calc R . . C14 C 0.69365(18) 1.1244(3) 0.44841(17) 0.0312(9) Uani 1 1 d . . . H14A H 0.6524 1.1666 0.4271 0.037 Uiso 1 1 calc R . . H14B H 0.7329 1.1621 0.4476 0.037 Uiso 1 1 calc R . . C15 C 0.67745(18) 0.8465(3) 0.33123(17) 0.0282(9) Uani 1 1 d . . . H15 H 0.7181 0.8462 0.3683 0.034 Uiso 1 1 calc R . . C16 C 0.64472(19) 0.9405(3) 0.30903(17) 0.0308(9) Uani 1 1 d . . . C17 C 0.5867(2) 0.9397(3) 0.25218(19) 0.0435(11) Uani 1 1 d . . . H17 H 0.5638 1.0014 0.2349 0.052 Uiso 1 1 calc R . . C18 C 0.5629(2) 0.8471(3) 0.22109(19) 0.0463(11) Uani 1 1 d . . . H18 H 0.5243 0.8458 0.1824 0.056 Uiso 1 1 calc R . . C19 C 0.5965(2) 0.7570(3) 0.24775(18) 0.0379(10) Uani 1 1 d . . . H19 H 0.5790 0.6944 0.2274 0.046 Uiso 1 1 calc R . . C20 C 0.74638(17) 1.0292(3) 0.55236(17) 0.0270(8) Uani 1 1 d . . . H20 H 0.7687 0.9858 0.5348 0.032 Uiso 1 1 calc R . . C21 C 0.70494(17) 1.1085(2) 0.51521(18) 0.0284(9) Uani 1 1 d . . . C22 C 0.67426(18) 1.1745(3) 0.5434(2) 0.0349(10) Uani 1 1 d . . . H22 H 0.6459 1.2287 0.5204 0.042 Uiso 1 1 calc R . . C23 C 0.68593(19) 1.1597(3) 0.6053(2) 0.0400(10) Uani 1 1 d . . . H23 H 0.6665 1.2048 0.6246 0.048 Uiso 1 1 calc R . . C24 C 0.72640(19) 1.0777(3) 0.63854(19) 0.0350(9) Uani 1 1 d . . . H24 H 0.7335 1.0675 0.6802 0.042 Uiso 1 1 calc R . . Cu1 Cu 0.69689(2) 0.62049(3) 0.34275(2) 0.02741(14) Uani 1 1 d . . . N1 N 0.94516(13) 0.7672(2) 0.51374(12) 0.0247(7) Uani 1 1 d . . . H101 H 0.9118 0.8151 0.4951 0.030 Uiso 1 1 calc R . . H102 H 0.9263 0.7152 0.5271 0.030 Uiso 1 1 calc R . . N2 N 0.78779(15) 0.6674(2) 0.34417(13) 0.0260(7) Uani 1 1 d . . . N3 N 0.89079(14) 0.9169(2) 0.64819(13) 0.0252(7) Uani 1 1 d . . . N4 N 0.68525(14) 1.0245(2) 0.41369(13) 0.0277(7) Uani 1 1 d . . . H103 H 0.6498 0.9886 0.4158 0.033 Uiso 1 1 calc R . . H104 H 0.7242 0.9864 0.4328 0.033 Uiso 1 1 calc R . . N5 N 0.65360(15) 0.7558(2) 0.30206(13) 0.0273(7) Uani 1 1 d . . . N6 N 0.75608(14) 1.0117(2) 0.61192(14) 0.0278(7) Uani 1 1 d . . . N7 N 0.67727(17) 0.5348(3) 0.20395(16) 0.0379(8) Uani 1 1 d . . . O1 O 0.65563(12) 0.53262(19) 0.24778(11) 0.0342(6) Uani 1 1 d . . . O2 O 0.7143(2) 0.4635(2) 0.20165(18) 0.0793(12) Uani 1 1 d . . . O3 O 0.66138(14) 0.6088(2) 0.16655(12) 0.0482(8) Uani 1 1 d . . . N8 N 0.63656(15) 0.4952(2) 0.03157(13) 0.0276(7) Uani 1 1 d . . . O4 O 0.65495(13) 0.58458(18) 0.02671(12) 0.0387(7) Uani 1 1 d . . . O5 O 0.67746(12) 0.41927(18) 0.03702(11) 0.0302(6) Uani 1 1 d . . . O6 O 0.57867(12) 0.47690(18) 0.03107(11) 0.0328(6) Uani 1 1 d . . . N9 N 0.52999(17) 0.0202(3) 0.92033(15) 0.0362(8) Uani 1 1 d . . . O7 O 0.57776(13) 0.08742(19) 0.92850(12) 0.0394(7) Uani 1 1 d . . . O8 O 0.53932(14) -0.0690(2) 0.90715(15) 0.0582(9) Uani 1 1 d . . . O9 O 0.47641(14) 0.0470(2) 0.92504(13) 0.0507(8) Uani 1 1 d . . . N10 N 1.0000 0.7159(5) 0.2500 0.0539(17) Uani 1 2 d SD . . O10 O 1.0000 0.6194(10) 0.2500 0.094(7) Uani 0.50 2 d SP A 1 O10' O 0.9877(12) 0.6371(12) 0.2104(9) 0.092(9) Uani 0.25 1 d PD . 2 O11 O 0.9405(8) 0.7454(11) 0.2013(6) 0.075(4) Uani 0.50 1 d P A 1 O11' O 0.9502(7) 0.7703(8) 0.2282(5) 0.052(3) Uani 0.50 1 d P A 2 N11 N 0.7438(5) 0.2376(8) 1.0007(6) 0.0213(17) Uiso 0.50 1 d P B -1 O12 O 0.6897(2) 0.1805(3) 0.9752(2) 0.0247(11) Uani 0.50 1 d P B -1 O13 O 0.7531(3) 0.3027(4) 0.9619(3) 0.0262(13) Uani 0.50 1 d P B -1 O14 O 0.7818(3) 0.2336(5) 1.0545(3) 0.0271(14) Uani 0.50 1 d P B -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.022(2) 0.044(2) 0.032(2) 0.0023(18) 0.0148(18) 0.0098(17) C2 0.0143(18) 0.032(2) 0.029(2) 0.0008(17) 0.0056(16) 0.0036(15) C3 0.033(2) 0.025(2) 0.028(2) 0.0052(16) 0.0205(19) 0.0044(16) C4 0.0196(19) 0.025(2) 0.030(2) 0.0013(16) 0.0135(17) 0.0072(15) C5 0.031(2) 0.036(2) 0.037(2) -0.0042(19) 0.021(2) -0.0068(17) C6 0.041(2) 0.049(3) 0.029(2) -0.0071(19) 0.021(2) -0.0177(19) C7 0.033(2) 0.034(2) 0.027(2) -0.0071(17) 0.0136(18) -0.0083(17) C8 0.025(2) 0.024(2) 0.028(2) 0.0038(16) 0.0107(17) 0.0025(15) C9 0.0199(18) 0.030(2) 0.0192(19) 0.0028(16) 0.0074(15) 0.0022(16) C10 0.025(2) 0.035(2) 0.033(2) 0.0009(18) 0.0161(18) -0.0030(17) C11 0.045(3) 0.030(2) 0.046(3) -0.0063(19) 0.027(2) -0.0120(18) C12 0.039(2) 0.026(2) 0.036(2) -0.0049(17) 0.0211(19) -0.0026(17) C13 0.035(2) 0.029(2) 0.040(2) 0.0076(18) 0.0166(19) 0.0041(17) C14 0.0202(19) 0.0180(19) 0.055(3) 0.0006(19) 0.0151(18) 0.0025(15) C15 0.026(2) 0.032(2) 0.031(2) 0.0024(17) 0.0161(17) -0.0023(16) C16 0.032(2) 0.029(2) 0.035(2) 0.0047(18) 0.0175(19) 0.0011(17) C17 0.049(3) 0.038(3) 0.036(3) 0.014(2) 0.011(2) 0.008(2) C18 0.047(3) 0.051(3) 0.029(2) 0.003(2) 0.004(2) 0.001(2) C19 0.042(3) 0.042(3) 0.028(2) -0.0016(19) 0.013(2) -0.005(2) C20 0.0204(19) 0.0212(19) 0.046(3) -0.0066(18) 0.0210(18) -0.0021(15) C21 0.0204(19) 0.0145(18) 0.053(3) -0.0051(17) 0.0179(18) -0.0034(15) C22 0.016(2) 0.021(2) 0.064(3) -0.008(2) 0.013(2) -0.0001(15) C23 0.027(2) 0.031(2) 0.067(3) -0.018(2) 0.024(2) 0.0011(18) C24 0.033(2) 0.032(2) 0.051(3) -0.015(2) 0.029(2) -0.0095(18) Cu1 0.0274(2) 0.0261(2) 0.0347(3) -0.0037(2) 0.0189(2) -0.0036(2) N1 0.0169(15) 0.0263(16) 0.0330(18) 0.0015(13) 0.0126(14) 0.0032(12) N2 0.0296(18) 0.0255(16) 0.0258(18) -0.0020(14) 0.0146(15) -0.0030(13) N3 0.0270(17) 0.0239(16) 0.0287(17) -0.0009(13) 0.0155(14) 0.0003(13) N4 0.0169(15) 0.0217(16) 0.042(2) 0.0018(14) 0.0101(14) 0.0034(12) N5 0.0281(18) 0.0318(18) 0.0249(17) -0.0032(14) 0.0138(15) -0.0033(14) N6 0.0269(17) 0.0237(16) 0.042(2) -0.0084(14) 0.0236(15) -0.0061(13) N7 0.037(2) 0.043(2) 0.042(2) -0.0177(18) 0.0248(18) -0.0210(17) O1 0.0383(16) 0.0421(16) 0.0325(15) -0.0097(12) 0.0249(13) -0.0106(12) O2 0.123(3) 0.050(2) 0.122(3) -0.003(2) 0.107(3) 0.007(2) O3 0.0504(18) 0.059(2) 0.0327(16) 0.0036(15) 0.0153(14) -0.0215(15) N8 0.0242(17) 0.0271(18) 0.0334(19) -0.0082(14) 0.0140(14) -0.0041(14) O4 0.0392(16) 0.0198(14) 0.0647(19) -0.0035(13) 0.0293(14) -0.0060(12) O5 0.0300(14) 0.0266(14) 0.0404(16) -0.0030(12) 0.0210(12) 0.0039(11) O6 0.0175(13) 0.0398(15) 0.0439(16) -0.0134(12) 0.0156(12) -0.0081(11) N9 0.033(2) 0.038(2) 0.039(2) 0.0071(16) 0.0166(16) 0.0098(17) O7 0.0383(16) 0.0322(15) 0.0569(18) 0.0028(13) 0.0291(14) 0.0046(12) O8 0.0405(18) 0.0395(18) 0.104(3) -0.0087(18) 0.0401(18) -0.0023(14) O9 0.0372(17) 0.061(2) 0.063(2) 0.0084(16) 0.0302(15) 0.0148(14) N10 0.081(5) 0.027(4) 0.096(6) 0.000 0.079(5) 0.000 O10 0.094(10) 0.011(6) 0.17(2) 0.000 0.044(15) 0.000 O10' 0.126(19) 0.045(10) 0.18(3) 0.039(13) 0.14(2) 0.033(11) O11 0.093(8) 0.071(8) 0.092(10) -0.027(6) 0.071(8) -0.039(6) O11' 0.061(6) 0.038(5) 0.073(8) 0.002(5) 0.044(6) 0.014(5) O12 0.011(2) 0.026(3) 0.037(3) -0.007(2) 0.010(2) -0.0095(19) O13 0.031(4) 0.020(3) 0.038(4) 0.009(3) 0.024(3) 0.001(3) O14 0.019(3) 0.029(4) 0.035(4) -0.003(3) 0.014(3) -0.003(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 C1 N1 1.489(4) . ? C1 C4 1.502(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N1 1.488(4) . ? C2 C9 1.505(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N2 1.332(4) . ? C3 C4 1.385(5) . ? C3 H3 0.9300 . ? C4 C5 1.372(5) . ? C5 C6 1.371(5) . ? C5 H5 0.9300 . ? C6 C7 1.383(5) . ? C6 H6 0.9300 . ? C7 N2 1.336(4) . ? C7 H7 0.9300 . ? C8 N3 1.348(4) . ? C8 C9 1.385(4) . ? C8 H8 0.9300 . ? C9 C10 1.386(5) . ? C10 C11 1.374(5) . ? C10 H10 0.9300 . ? C11 C12 1.378(5) . ? C11 H11 0.9300 . ? C12 N3 1.336(4) . ? C12 H12 0.9300 . ? C13 N4 1.494(4) . ? C13 C16 1.505(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N4 1.490(4) . ? C14 C21 1.490(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N5 1.338(4) . ? C15 C16 1.383(5) . ? C15 H15 0.9300 . ? C16 C17 1.379(5) . ? C17 C18 1.376(5) . ? C17 H17 0.9300 . ? C18 C19 1.365(5) . ? C18 H18 0.9300 . ? C19 N5 1.336(4) . ? C19 H19 0.9300 . ? C20 N6 1.337(4) . ? C20 C21 1.387(5) . ? C20 H20 0.9300 . ? C21 C22 1.392(5) . ? C22 C23 1.372(5) . ? C22 H22 0.9300 . ? C23 C24 1.375(5) . ? C23 H23 0.9300 . ? C24 N6 1.353(4) . ? C24 H24 0.9300 . ? Cu1 N2 2.004(3) . ? Cu1 N5 2.011(3) . ? Cu1 N3 2.013(3) 7_666 ? Cu1 N6 2.030(3) 7_666 ? Cu1 O1 2.309(2) . ? N1 H101 0.9000 . ? N1 H102 0.9000 . ? N3 Cu1 2.013(3) 7_666 ? N4 H103 0.9000 . ? N4 H104 0.9000 . ? N6 Cu1 2.030(3) 7_666 ? N7 O2 1.223(4) . ? N7 O3 1.239(4) . ? N7 O1 1.285(4) . ? N8 O4 1.235(3) . ? N8 O6 1.244(3) . ? N8 O5 1.276(3) . ? N9 O8 1.225(4) . ? N9 O9 1.234(4) . ? N9 O7 1.283(4) . ? N10 O11' 1.188(12) 2_755 ? N10 O11' 1.188(12) . ? N10 O10 1.241(15) . ? N10 O10' 1.323(18) 2_755 ? N10 O10' 1.323(18) . ? N10 O11 1.349(17) 2_755 ? N10 O11 1.349(17) . ? O10' O10' 1.70(4) 2_755 ? N11 O14 1.176(15) . ? N11 O12 1.279(9) . ? N11 O13 1.307(17) . ? 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 C1 C4 111.3(3) . . ? N1 C1 H1A 109.4 . . ? C4 C1 H1A 109.4 . . ? N1 C1 H1B 109.4 . . ? C4 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? N1 C2 C9 111.9(3) . . ? N1 C2 H2A 109.2 . . ? C9 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C9 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N2 C3 C4 123.3(3) . . ? N2 C3 H3 118.3 . . ? C4 C3 H3 118.3 . . ? C5 C4 C3 117.5(3) . . ? C5 C4 C1 121.2(3) . . ? C3 C4 C1 121.3(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 119.1(3) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? N2 C7 C6 121.7(3) . . ? N2 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? N3 C8 C9 122.8(3) . . ? N3 C8 H8 118.6 . . ? C9 C8 H8 118.6 . . ? C8 C9 C10 117.9(3) . . ? C8 C9 C2 122.3(3) . . ? C10 C9 C2 119.7(3) . . ? C11 C10 C9 119.4(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 119.3(3) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? N3 C12 C11 122.3(3) . . ? N3 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? N4 C13 C16 111.1(3) . . ? N4 C13 H13A 109.4 . . ? C16 C13 H13A 109.4 . . ? N4 C13 H13B 109.4 . . ? C16 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? N4 C14 C21 112.4(3) . . ? N4 C14 H14A 109.1 . . ? C21 C14 H14A 109.1 . . ? N4 C14 H14B 109.1 . . ? C21 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? N5 C15 C16 123.3(3) . . ? N5 C15 H15 118.3 . . ? C16 C15 H15 118.3 . . ? C17 C16 C15 117.2(4) . . ? C17 C16 C13 121.8(3) . . ? C15 C16 C13 121.0(3) . . ? C18 C17 C16 119.7(4) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 119.2(4) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? N5 C19 C18 122.3(4) . . ? N5 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? N6 C20 C21 123.7(3) . . ? N6 C20 H20 118.1 . . ? C21 C20 H20 118.1 . . ? C20 C21 C22 116.8(4) . . ? C20 C21 C14 122.5(3) . . ? C22 C21 C14 120.7(3) . . ? C23 C22 C21 119.9(4) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 119.7(3) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? N6 C24 C23 121.4(4) . . ? N6 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? N2 Cu1 N5 89.51(11) . . ? N2 Cu1 N3 172.70(11) . 7_666 ? N5 Cu1 N3 89.92(11) . 7_666 ? N2 Cu1 N6 89.20(11) . 7_666 ? N5 Cu1 N6 176.89(12) . 7_666 ? N3 Cu1 N6 91.00(11) 7_666 7_666 ? N2 Cu1 O1 97.88(10) . . ? N5 Cu1 O1 93.22(10) . . ? N3 Cu1 O1 89.42(10) 7_666 . ? N6 Cu1 O1 89.76(10) 7_666 . ? C2 N1 C1 113.8(2) . . ? C2 N1 H101 108.8 . . ? C1 N1 H101 108.8 . . ? C2 N1 H102 108.8 . . ? C1 N1 H102 108.8 . . ? H101 N1 H102 107.7 . . ? C3 N2 C7 118.3(3) . . ? C3 N2 Cu1 120.5(2) . . ? C7 N2 Cu1 121.1(2) . . ? C12 N3 C8 118.2(3) . . ? C12 N3 Cu1 119.8(2) . 7_666 ? C8 N3 Cu1 121.9(2) . 7_666 ? C14 N4 C13 113.1(3) . . ? C14 N4 H103 109.0 . . ? C13 N4 H103 109.0 . . ? C14 N4 H104 109.0 . . ? C13 N4 H104 109.0 . . ? H103 N4 H104 107.8 . . ? C19 N5 C15 118.1(3) . . ? C19 N5 Cu1 120.7(3) . . ? C15 N5 Cu1 120.9(2) . . ? C20 N6 C24 118.3(3) . . ? C20 N6 Cu1 120.7(2) . 7_666 ? C24 N6 Cu1 120.5(3) . 7_666 ? O2 N7 O3 122.3(3) . . ? O2 N7 O1 117.9(4) . . ? O3 N7 O1 119.7(3) . . ? N7 O1 Cu1 129.5(2) . . ? O4 N8 O6 121.5(3) . . ? O4 N8 O5 119.7(3) . . ? O6 N8 O5 118.8(3) . . ? O8 N9 O9 122.4(3) . . ? O8 N9 O7 117.9(3) . . ? O9 N9 O7 119.7(3) . . ? O11' N10 O11' 107.8(12) 2_755 . ? O11' N10 O10 126.1(6) 2_755 . ? O11' N10 O10 126.1(6) . . ? O11' N10 O10' 105.9(11) 2_755 2_755 ? O11' N10 O10' 129.1(12) . 2_755 ? O10 N10 O10' 39.9(7) . 2_755 ? O11' N10 O10' 129.1(12) 2_755 . ? O11' N10 O10' 105.9(11) . . ? O10 N10 O10' 39.9(7) . . ? O10' N10 O10' 79.9(14) 2_755 . ? O11' N10 O11 29.1(5) 2_755 2_755 ? O11' N10 O11 122.8(8) . 2_755 ? O10 N10 O11 106.4(6) . 2_755 ? O10' N10 O11 77.7(11) 2_755 2_755 ? O10' N10 O11 130.2(12) . 2_755 ? O11' N10 O11 122.8(8) 2_755 . ? O11' N10 O11 29.1(5) . . ? O10 N10 O11 106.4(6) . . ? O10' N10 O11 130.2(12) 2_755 . ? O10' N10 O11 77.7(11) . . ? O11 N10 O11 147.3(12) 2_755 . ? N10 O10' O10' 50.1(7) . 2_755 ? O14 N11 O12 123.3(13) . . ? O14 N11 O13 122.3(7) . . ? O12 N11 O13 114.3(11) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.405 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.069 # Attachment '- cpd 2_revised.cif' data_cpd2 _database_code_depnum_ccdc_archive 'CCDC 796951' #TrackingRef '- cpd 2_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H28 Cu N10 O6 S2' _chemical_formula_weight 704.24 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' 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.445(7) _cell_length_b 8.734(4) _cell_length_c 20.526(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2948(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1745 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 24.49 _exptl_crystal_description plate _exptl_crystal_colour pale-green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 0.943 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5798 _exptl_absorpt_correction_T_max 0.7451 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 10041 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2607 _reflns_number_gt 1727 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0507P)^2^+0.7699P] 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 2607 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6532(2) -0.0379(5) 0.26786(14) 0.0283(10) Uani 1 1 d . . . H1A H 0.7060 -0.0240 0.2477 0.034 Uiso 1 1 calc R . . H1B H 0.6431 -0.1470 0.2713 0.034 Uiso 1 1 calc R . . C2 C 0.59317(19) -0.0382(4) 0.16046(14) 0.0220(9) Uani 1 1 d . . . H2A H 0.5837 -0.1475 0.1640 0.026 Uiso 1 1 calc R . . H2B H 0.6467 -0.0232 0.1417 0.026 Uiso 1 1 calc R . . C3 C 0.59228(18) 0.0037(4) 0.37747(15) 0.0196(8) Uani 1 1 d . . . H3 H 0.5478 -0.0526 0.3631 0.024 Uiso 1 1 calc R . . C4 C 0.65444(18) 0.0307(4) 0.33478(15) 0.0208(9) Uani 1 1 d . . . C5 C 0.71919(18) 0.1179(5) 0.35546(16) 0.0238(9) Uani 1 1 d . . . H5 H 0.7622 0.1388 0.3275 0.029 Uiso 1 1 calc R . . C6 C 0.71933(18) 0.1733(4) 0.41766(16) 0.0232(8) Uani 1 1 d . . . H6 H 0.7618 0.2345 0.4324 0.028 Uiso 1 1 calc R . . C7 C 0.65586(19) 0.1373(4) 0.45787(15) 0.0207(8) Uani 1 1 d . . . H7 H 0.6570 0.1723 0.5006 0.025 Uiso 1 1 calc R . . C8 C 0.54206(18) 0.1723(4) 0.08843(14) 0.0195(8) Uani 1 1 d . . . H8 H 0.5882 0.2273 0.1002 0.023 Uiso 1 1 calc R . . C9 C 0.53091(19) 0.0302(4) 0.11661(15) 0.0187(8) Uani 1 1 d . . . C10 C 0.4616(2) -0.0516(4) 0.10089(15) 0.0225(9) Uani 1 1 d . . . H10 H 0.4512 -0.1467 0.1195 0.027 Uiso 1 1 calc R . . C11 C 0.4089(2) 0.0122(4) 0.05699(15) 0.0231(9) Uani 1 1 d . . . H11 H 0.3618 -0.0394 0.0451 0.028 Uiso 1 1 calc R . . C12 C 0.42629(19) 0.1530(4) 0.03066(14) 0.0196(8) Uani 1 1 d . . . H12 H 0.3900 0.1928 0.0003 0.023 Uiso 1 1 calc R . . C13 C 0.6435(2) -0.0962(4) 0.58150(15) 0.0205(8) Uani 1 1 d . . . N1 N 0.59072(16) 0.0315(4) 0.22641(12) 0.0222(7) Uani 1 1 d . . . H101 H 0.5994 0.1330 0.2234 0.027 Uiso 1 1 calc R . . H102 H 0.5414 0.0167 0.2443 0.027 Uiso 1 1 calc R . . N2 N 0.59234(15) 0.0541(3) 0.43842(12) 0.0181(7) Uani 1 1 d . . . N3 N 0.49132(14) 0.2365(4) 0.04545(11) 0.0179(7) Uani 1 1 d . . . N4 N 0.58002(16) -0.0476(4) 0.56788(12) 0.0225(7) Uani 1 1 d . . . N5 N 0.10485(18) 0.4310(4) 0.25925(14) 0.0314(8) Uani 1 1 d . . . O1 O 0.0997(2) 0.5723(4) 0.24746(13) 0.0551(9) Uani 1 1 d . . . O2 O 0.16748(16) 0.3543(4) 0.26088(16) 0.0615(10) Uani 1 1 d . . . O3 O 0.04064(14) 0.3547(3) 0.27062(11) 0.0360(7) Uani 1 1 d . . . Cu1 Cu 0.5000 0.0000 0.5000 0.01910(19) Uani 1 2 d S . . S1 S 0.73025(5) -0.16988(13) 0.59924(5) 0.0342(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0202(18) 0.048(3) 0.0162(17) 0.0022(18) -0.0013(13) 0.0146(18) C2 0.0198(17) 0.031(3) 0.0146(16) 0.0001(17) 0.0015(13) 0.0015(16) C3 0.0135(16) 0.024(2) 0.0209(17) 0.0002(17) -0.0025(13) 0.0011(16) C4 0.0140(16) 0.030(3) 0.0182(16) 0.0050(17) -0.0026(13) 0.0092(15) C5 0.0127(17) 0.034(3) 0.0246(17) 0.0068(18) 0.0034(13) 0.0010(16) C6 0.0113(16) 0.025(2) 0.0327(19) 0.0020(19) -0.0040(14) -0.0015(15) C7 0.0199(17) 0.023(2) 0.0192(16) -0.0012(17) -0.0023(13) 0.0054(16) C8 0.0135(16) 0.026(2) 0.0188(16) -0.0041(18) 0.0021(13) -0.0022(16) C9 0.0175(16) 0.023(2) 0.0157(16) -0.0020(17) 0.0036(13) 0.0029(15) C10 0.0256(18) 0.020(2) 0.0222(18) 0.0001(17) 0.0051(15) -0.0027(17) C11 0.0181(16) 0.028(3) 0.0234(17) -0.0027(18) -0.0005(13) -0.0037(17) C12 0.0190(17) 0.024(2) 0.0156(16) -0.0003(17) 0.0021(13) 0.0052(16) C13 0.0193(18) 0.026(2) 0.0162(16) 0.0024(17) 0.0026(14) -0.0044(16) N1 0.0211(14) 0.025(2) 0.0204(14) 0.0001(14) -0.0024(11) 0.0037(13) N2 0.0137(13) 0.0228(19) 0.0179(13) -0.0005(14) -0.0015(11) 0.0028(13) N3 0.0151(13) 0.0234(19) 0.0150(12) -0.0010(13) 0.0025(11) -0.0001(13) N4 0.0188(15) 0.032(2) 0.0168(14) -0.0012(14) -0.0003(12) 0.0007(14) N5 0.0262(18) 0.043(3) 0.0252(17) -0.0028(18) 0.0028(13) -0.0026(18) O1 0.096(3) 0.033(2) 0.0356(16) 0.0102(16) -0.0204(16) -0.027(2) O2 0.0233(15) 0.066(3) 0.095(2) -0.032(2) -0.0021(15) 0.0005(16) O3 0.0182(13) 0.052(2) 0.0375(14) 0.0101(15) 0.0000(11) -0.0018(13) Cu1 0.0115(3) 0.0304(4) 0.0153(3) 0.0008(3) -0.0005(2) 0.0023(3) S1 0.0141(4) 0.0377(7) 0.0508(6) -0.0012(6) -0.0062(4) 0.0042(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 C1 N1 1.465(4) . ? C1 C4 1.499(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N1 1.485(4) . ? C2 C9 1.488(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N2 1.326(4) . ? C3 C4 1.367(4) . ? C3 H3 0.9300 . ? C4 C5 1.376(5) . ? C5 C6 1.365(5) . ? C5 H5 0.9300 . ? C6 C7 1.367(4) . ? C6 H6 0.9300 . ? C7 N2 1.334(4) . ? C7 H7 0.9300 . ? C8 N3 1.337(4) . ? C8 C9 1.382(5) . ? C8 H8 0.9300 . ? C9 C10 1.383(5) . ? C10 C11 1.368(5) . ? C10 H10 0.9300 . ? C11 C12 1.374(5) . ? C11 H11 0.9300 . ? C12 N3 1.329(4) . ? C12 H12 0.9300 . ? C13 N4 1.161(4) . ? C13 S1 1.606(4) . ? N1 H101 0.9000 . ? N1 H102 0.9000 . ? N2 Cu1 2.031(3) . ? N4 Cu1 1.961(3) . ? N5 O2 1.229(4) . ? N5 O1 1.261(4) . ? N5 O3 1.270(4) . ? Cu1 N4 1.961(3) 5_656 ? Cu1 N2 2.031(3) 5_656 ? 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 C1 C4 112.1(3) . . ? N1 C1 H1A 109.2 . . ? C4 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C4 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? N1 C2 C9 111.6(3) . . ? N1 C2 H2A 109.3 . . ? C9 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C9 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? N2 C3 C4 123.2(3) . . ? N2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? C3 C4 C5 118.4(3) . . ? C3 C4 C1 120.6(3) . . ? C5 C4 C1 121.0(3) . . ? C6 C5 C4 119.1(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 118.8(3) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? N2 C7 C6 122.9(3) . . ? N2 C7 H7 118.6 . . ? C6 C7 H7 118.6 . . ? N3 C8 C9 124.7(3) . . ? N3 C8 H8 117.6 . . ? C9 C8 H8 117.6 . . ? C8 C9 C10 118.4(3) . . ? C8 C9 C2 121.5(3) . . ? C10 C9 C2 120.0(3) . . ? C11 C10 C9 117.7(3) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? C10 C11 C12 119.5(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? N3 C12 C11 124.6(3) . . ? N3 C12 H12 117.7 . . ? C11 C12 H12 117.7 . . ? N4 C13 S1 177.8(4) . . ? C1 N1 C2 109.9(3) . . ? C1 N1 H101 109.7 . . ? C2 N1 H101 109.7 . . ? C1 N1 H102 109.7 . . ? C2 N1 H102 109.7 . . ? H101 N1 H102 108.2 . . ? C3 N2 C7 117.6(3) . . ? C3 N2 Cu1 120.6(2) . . ? C7 N2 Cu1 121.7(2) . . ? C12 N3 C8 115.0(3) . . ? C13 N4 Cu1 148.4(3) . . ? O2 N5 O1 126.5(4) . . ? O2 N5 O3 113.9(4) . . ? O1 N5 O3 119.5(3) . . ? N4 Cu1 N4 180.0 . 5_656 ? N4 Cu1 N2 90.58(11) . 5_656 ? N4 Cu1 N2 89.42(11) 5_656 5_656 ? N4 Cu1 N2 89.42(11) . . ? N4 Cu1 N2 90.58(11) 5_656 . ? N2 Cu1 N2 180.0 5_656 . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.585 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.080 # Attachment '- cpd 3_revised.cif' data_cpd3 _database_code_depnum_ccdc_archive 'CCDC 796952' #TrackingRef '- cpd 3_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 Cu N9' _chemical_formula_weight 346.85 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' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.1442(5) _cell_length_b 18.2183(11) _cell_length_c 9.8054(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.714(2) _cell_angle_gamma 90.00 _cell_volume 1441.70(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4263 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 24.93 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 1.527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6046 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 14800 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2540 _reflns_number_gt 2132 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0242P)^2^+1.3690P] 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 2540 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0646 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.19825(4) 0.486867(16) 0.48177(3) 0.01270(10) Uani 1 1 d . . . N1 N 0.5119(3) 0.67017(11) 1.0493(2) 0.0172(5) Uani 1 1 d . . . H101 H 0.5935 0.6608 1.1206 0.026 Uiso 1 1 d R . . N2 N 0.2742(2) 0.57253(11) 0.6063(2) 0.0135(4) Uani 1 1 d . . . N3 N 0.3523(2) 0.89687(11) 1.1370(2) 0.0136(4) Uani 1 1 d . . . N4 N 0.3244(3) 0.52492(11) 0.3347(2) 0.0168(5) Uani 1 1 d . . . N5 N 0.4489(3) 0.56014(11) 0.35909(19) 0.0136(5) Uani 1 1 d . . . N6 N 0.5712(3) 0.59444(11) 0.3770(2) 0.0179(5) Uani 1 1 d . . . N7 N 0.0464(2) 0.45146(11) 0.6123(2) 0.0148(4) Uani 1 1 d . . . N8 N 0.0840(3) 0.41840(11) 0.7166(2) 0.0179(5) Uani 1 1 d . . . N9 N 0.1163(3) 0.38619(16) 0.8175(3) 0.0424(7) Uani 1 1 d . . . C1 C 0.4962(3) 0.60392(13) 0.9648(2) 0.0182(6) Uani 1 1 d . . . H1C H 0.4307 0.5679 1.0066 0.022 Uiso 1 1 calc R . . H1D H 0.6053 0.5832 0.9615 0.022 Uiso 1 1 calc R . . C2 C 0.3554(3) 0.69177(13) 1.0954(2) 0.0163(5) Uani 1 1 d . . . H2A H 0.3244 0.6558 1.1604 0.020 Uiso 1 1 calc R . . H2B H 0.2687 0.6933 1.0173 0.020 Uiso 1 1 calc R . . C3 C 0.3444(3) 0.56346(13) 0.7378(2) 0.0139(5) Uani 1 1 d . . . H3 H 0.3455 0.5166 0.7754 0.017 Uiso 1 1 calc R . . C4 C 0.4149(3) 0.61993(13) 0.8198(2) 0.0154(5) Uani 1 1 d . . . C5 C 0.4089(3) 0.68993(14) 0.7637(2) 0.0176(6) Uani 1 1 d . . . H5 H 0.4571 0.7292 0.8148 0.021 Uiso 1 1 calc R . . C6 C 0.3305(3) 0.70080(13) 0.6311(3) 0.0182(6) Uani 1 1 d . . . H6 H 0.3214 0.7477 0.5934 0.022 Uiso 1 1 calc R . . C7 C 0.2661(3) 0.64107(13) 0.5556(2) 0.0153(5) Uani 1 1 d . . . H7 H 0.2150 0.6486 0.4661 0.018 Uiso 1 1 calc R . . C8 C 0.3384(3) 0.82886(13) 1.0847(2) 0.0149(5) Uani 1 1 d . . . H8 H 0.3040 0.8236 0.9909 0.018 Uiso 1 1 calc R . . C9 C 0.3725(3) 0.76606(13) 1.1628(2) 0.0138(5) Uani 1 1 d . . . C10 C 0.4253(3) 0.77467(14) 1.3025(2) 0.0178(6) Uani 1 1 d . . . H10 H 0.4508 0.7339 1.3583 0.021 Uiso 1 1 calc R . . C11 C 0.4396(3) 0.84448(14) 1.3578(3) 0.0179(6) Uani 1 1 d . . . H11 H 0.4746 0.8512 1.4512 0.021 Uiso 1 1 calc R . . C12 C 0.4014(3) 0.90405(14) 1.2730(2) 0.0161(5) Uani 1 1 d . . . H12 H 0.4099 0.9509 1.3110 0.019 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01379(17) 0.01467(16) 0.00978(16) -0.00040(12) 0.00209(11) -0.00223(12) N1 0.0180(12) 0.0176(11) 0.0143(11) -0.0033(9) -0.0044(9) 0.0026(9) N2 0.0104(11) 0.0162(11) 0.0143(11) -0.0007(8) 0.0032(8) -0.0001(8) N3 0.0125(11) 0.0168(11) 0.0116(10) -0.0007(8) 0.0024(8) 0.0010(8) N4 0.0148(12) 0.0212(12) 0.0143(11) -0.0023(9) 0.0019(8) -0.0061(9) N5 0.0172(13) 0.0154(11) 0.0083(10) 0.0012(8) 0.0029(8) 0.0056(9) N6 0.0115(11) 0.0207(12) 0.0215(12) -0.0023(9) 0.0024(9) -0.0036(9) N7 0.0136(11) 0.0193(11) 0.0109(11) 0.0034(9) -0.0001(8) 0.0008(9) N8 0.0142(12) 0.0225(12) 0.0178(12) 0.0019(10) 0.0054(9) 0.0007(9) N9 0.0338(16) 0.066(2) 0.0298(15) 0.0312(14) 0.0124(12) 0.0161(13) C1 0.0208(14) 0.0163(14) 0.0162(14) -0.0014(11) -0.0025(11) 0.0023(10) C2 0.0177(14) 0.0178(13) 0.0126(13) 0.0027(10) -0.0007(10) -0.0007(10) C3 0.0138(13) 0.0132(12) 0.0152(13) -0.0002(10) 0.0033(10) 0.0000(10) C4 0.0143(13) 0.0182(13) 0.0140(13) -0.0033(10) 0.0028(10) 0.0028(10) C5 0.0201(14) 0.0161(13) 0.0165(13) -0.0041(10) 0.0021(11) -0.0021(11) C6 0.0249(15) 0.0141(13) 0.0165(13) 0.0015(10) 0.0058(11) 0.0005(11) C7 0.0127(13) 0.0212(14) 0.0123(13) 0.0005(10) 0.0028(10) 0.0020(10) C8 0.0138(13) 0.0215(14) 0.0095(12) -0.0017(10) 0.0021(10) -0.0008(10) C9 0.0115(13) 0.0165(13) 0.0138(13) -0.0008(10) 0.0034(10) 0.0001(10) C10 0.0196(14) 0.0195(14) 0.0144(13) 0.0040(10) 0.0033(11) 0.0020(11) C11 0.0201(14) 0.0236(14) 0.0096(12) -0.0010(10) 0.0011(10) 0.0014(11) C12 0.0174(14) 0.0170(13) 0.0141(13) -0.0027(10) 0.0026(10) 0.0016(10) _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 N7 2.002(2) . ? Cu1 N4 2.004(2) . ? Cu1 N3 2.021(2) 2_546 ? Cu1 N2 2.027(2) . ? Cu1 N7 2.364(2) 3_566 ? N1 C1 1.460(3) . ? N1 C2 1.462(3) . ? N1 H101 0.9139 . ? N2 C7 1.342(3) . ? N2 C3 1.348(3) . ? N3 C8 1.340(3) . ? N3 C12 1.346(3) . ? N3 Cu1 2.021(2) 2_556 ? N4 N5 1.196(3) . ? N5 N6 1.169(3) . ? N7 N8 1.191(3) . ? N7 Cu1 2.364(2) 3_566 ? N8 N9 1.150(3) . ? C1 C4 1.514(3) . ? C1 H1C 0.9700 . ? C1 H1D 0.9700 . ? C2 C9 1.504(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.382(3) . ? C3 H3 0.9300 . ? C4 C5 1.387(3) . ? C5 C6 1.383(3) . ? C5 H5 0.9300 . ? C6 C7 1.379(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.384(3) . ? C8 H8 0.9300 . ? C9 C10 1.389(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C11 C12 1.377(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 Cu1 N4 172.80(8) . . ? N7 Cu1 N3 90.66(8) . 2_546 ? N4 Cu1 N3 87.16(8) . 2_546 ? N7 Cu1 N2 91.58(8) . . ? N4 Cu1 N2 91.31(8) . . ? N3 Cu1 N2 173.72(8) 2_546 . ? N7 Cu1 N7 80.90(8) . 3_566 ? N4 Cu1 N7 92.38(8) . 3_566 ? N3 Cu1 N7 93.72(8) 2_546 3_566 ? N2 Cu1 N7 92.42(7) . 3_566 ? C1 N1 C2 112.61(19) . . ? C1 N1 H101 106.2 . . ? C2 N1 H101 112.8 . . ? C7 N2 C3 117.5(2) . . ? C7 N2 Cu1 119.81(16) . . ? C3 N2 Cu1 122.53(16) . . ? C8 N3 C12 117.9(2) . . ? C8 N3 Cu1 121.99(16) . 2_556 ? C12 N3 Cu1 120.15(16) . 2_556 ? N5 N4 Cu1 122.98(16) . . ? N6 N5 N4 177.1(2) . . ? N8 N7 Cu1 127.03(17) . . ? N8 N7 Cu1 132.95(16) . 3_566 ? Cu1 N7 Cu1 99.10(8) . 3_566 ? N9 N8 N7 178.4(3) . . ? N1 C1 C4 111.6(2) . . ? N1 C1 H1C 109.3 . . ? C4 C1 H1C 109.3 . . ? N1 C1 H1D 109.3 . . ? C4 C1 H1D 109.3 . . ? H1C C1 H1D 108.0 . . ? N1 C2 C9 110.19(19) . . ? N1 C2 H2A 109.6 . . ? C9 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C9 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N2 C3 C4 123.7(2) . . ? N2 C3 H3 118.2 . . ? C4 C3 H3 118.2 . . ? C3 C4 C5 117.6(2) . . ? C3 C4 C1 119.9(2) . . ? C5 C4 C1 122.5(2) . . ? C6 C5 C4 119.4(2) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C7 C6 C5 119.1(2) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? N2 C7 C6 122.6(2) . . ? N2 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? N3 C8 C9 123.6(2) . . ? N3 C8 H8 118.2 . . ? C9 C8 H8 118.2 . . ? C8 C9 C10 117.7(2) . . ? C8 C9 C2 120.1(2) . . ? C10 C9 C2 122.2(2) . . ? C11 C10 C9 119.3(2) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 119.2(2) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? N3 C12 C11 122.3(2) . . ? N3 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.319 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.067