####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_complex1 _database_code_depnum_ccdc_archive 'CCDC 290150' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H44 Cu4 N16 O8' _chemical_formula_weight 962.93 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 P21/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 8.284(8) _cell_length_b 21.524(12) _cell_length_c 11.432(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.19(2) _cell_angle_gamma 90.00 _cell_volume 1967(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 17 _exptl_crystal_description prisme _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 2.198 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.768 _exptl_absorpt_correction_T_max 0.803 _exptl_absorpt_process_details ? _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 'four cicle diffractometer' _diffrn_measurement_method '\w-2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5957 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0707 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 29.97 _reflns_number_total 5708 _reflns_number_gt 3320 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0546P)^2^+0.6578P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens '20 geom and 2 difmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5708 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1282 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.71885(6) 0.034813(19) 0.38579(4) 0.03562(13) Uani 1 1 d . . . Cu2 Cu 0.65813(6) 0.195278(19) 0.34760(4) 0.04072(14) Uani 1 1 d . . . O1 O 0.7210(3) 0.11366(10) 0.3067(2) 0.0378(6) Uani 1 1 d . . . O2 O 0.6856(4) 0.17425(14) 0.5175(3) 0.0617(8) Uani 1 1 d . . . O3 O 0.7144(4) 0.07157(12) 0.5431(2) 0.0482(7) Uani 1 1 d . . . O4 O 0.4444(5) 0.01760(18) 0.3399(4) 0.0554(9) Uani 1 1 d . . . N1 N 0.6838(4) 0.22032(15) 0.1817(3) 0.0446(8) Uani 1 1 d . . . N2 N 0.7537(4) -0.00206(14) 0.2297(3) 0.0362(7) Uani 1 1 d . . . N3 N 0.6438(5) 0.28301(17) 0.3980(4) 0.0637(10) Uani 1 1 d . . . N4 N 0.5511(5) 0.36769(18) 0.5065(4) 0.0644(10) Uani 1 1 d . . . N5 N 0.7240(5) 0.45326(19) 0.6119(3) 0.0637(10) Uani 1 1 d . . . N6 N 0.3743(5) 0.18299(18) 0.2950(4) 0.0624(10) Uani 1 1 d . . . N7 N 0.1790(5) 0.13576(18) 0.3959(4) 0.0637(11) Uani 1 1 d . . . N8 N 0.2190(5) 0.04542(15) 0.5273(3) 0.0495(8) Uani 1 1 d . . . C1 C 0.6585(5) 0.16170(18) 0.1124(4) 0.0463(9) Uani 1 1 d . . . H1 H 0.6990 0.1662 0.0405 0.056 Uiso 1 1 calc R . . H1A H 0.5402 0.1518 0.0869 0.056 Uiso 1 1 calc R . . C2 C 0.7523(5) 0.10995(17) 0.1910(3) 0.0388(8) Uani 1 1 d . . . H2 H 0.8725 0.1145 0.1992 0.047 Uiso 1 1 calc R . . C3 C 0.6941(5) 0.04710(17) 0.1370(3) 0.0407(9) Uani 1 1 d . . . H3 H 0.5729 0.0463 0.1099 0.049 Uiso 1 1 calc R . . H3A H 0.7378 0.0395 0.0675 0.049 Uiso 1 1 calc R . . C4 C 0.8554(6) 0.2454(2) 0.1953(5) 0.0649(13) Uani 1 1 d . . . H4 H 0.8722 0.2531 0.1166 0.078 Uiso 1 1 calc R . . H4A H 0.9364 0.2157 0.2376 0.078 Uiso 1 1 calc R . . H4B H 0.8682 0.2835 0.2404 0.078 Uiso 1 1 calc R . . C5 C 0.5581(6) 0.2667(2) 0.1177(4) 0.0602(12) Uani 1 1 d . . . H5 H 0.5741 0.3050 0.1624 0.072 Uiso 1 1 calc R . . H5A H 0.4475 0.2512 0.1115 0.072 Uiso 1 1 calc R . . H5B H 0.5717 0.2739 0.0380 0.072 Uiso 1 1 calc R . . C6 C 0.9349(5) -0.0146(2) 0.2474(4) 0.0487(10) Uani 1 1 d . . . H6 H 0.9693 -0.0473 0.3058 0.058 Uiso 1 1 calc R . . H6A H 0.9977 0.0223 0.2762 0.058 Uiso 1 1 calc R . . H6B H 0.9548 -0.0270 0.1717 0.058 Uiso 1 1 calc R . . C7 C 0.6588(5) -0.05984(18) 0.1892(4) 0.0495(10) Uani 1 1 d . . . H7 H 0.6759 -0.0726 0.1128 0.059 Uiso 1 1 calc R . . H7A H 0.5419 -0.0525 0.1801 0.059 Uiso 1 1 calc R . . H7B H 0.6972 -0.0919 0.2483 0.059 Uiso 1 1 calc R . . C8 C 0.7052(5) 0.12629(18) 0.5806(3) 0.0378(8) Uani 1 1 d . . . C9 C 0.7149(6) 0.1348(2) 0.7122(4) 0.0528(10) Uani 1 1 d . . . H9 H 0.7449 0.1771 0.7351 0.063 Uiso 1 1 calc R . . H9A H 0.7980 0.1074 0.7596 0.063 Uiso 1 1 calc R . . H9B H 0.6082 0.1256 0.7262 0.063 Uiso 1 1 calc R . . C10 C 0.6094(5) 0.3234(2) 0.4526(4) 0.0501(10) Uani 1 1 d . . . C11 C 0.6496(5) 0.4118(2) 0.5637(3) 0.0460(9) Uani 1 1 d . . . C12 C 0.2901(5) 0.15894(18) 0.3453(4) 0.0440(9) Uani 1 1 d . . . C13 C 0.2096(5) 0.08774(18) 0.4657(3) 0.0398(8) Uani 1 1 d . . . H4O H 0.404(5) 0.025(2) 0.290(4) 0.030(14) Uiso 1 1 d . . . H4OA H 0.401(6) -0.006(2) 0.374(4) 0.055(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0474(3) 0.0281(2) 0.0330(2) 0.00281(17) 0.01337(19) 0.00506(19) Cu2 0.0516(3) 0.0260(2) 0.0431(3) -0.00048(19) 0.0097(2) -0.00351(19) O1 0.0528(16) 0.0291(12) 0.0337(13) 0.0023(10) 0.0150(12) 0.0035(11) O2 0.105(3) 0.0368(15) 0.0407(16) -0.0012(13) 0.0136(16) -0.0022(16) O3 0.0742(19) 0.0386(15) 0.0342(14) 0.0010(11) 0.0184(13) 0.0074(13) O4 0.052(2) 0.063(2) 0.053(2) 0.0185(18) 0.0162(18) 0.0003(16) N1 0.0445(19) 0.0359(17) 0.053(2) 0.0124(15) 0.0128(15) 0.0026(14) N2 0.0385(17) 0.0344(16) 0.0377(16) -0.0018(13) 0.0131(13) 0.0009(13) N3 0.088(3) 0.0330(19) 0.067(3) -0.0030(18) 0.015(2) -0.0040(19) N4 0.059(2) 0.056(2) 0.083(3) -0.016(2) 0.028(2) -0.0051(19) N5 0.079(3) 0.057(2) 0.053(2) -0.0142(19) 0.013(2) 0.001(2) N6 0.053(2) 0.050(2) 0.088(3) 0.007(2) 0.024(2) -0.0057(18) N7 0.066(2) 0.051(2) 0.082(3) 0.032(2) 0.036(2) 0.0246(18) N8 0.071(2) 0.0369(18) 0.0443(18) 0.0105(14) 0.0219(17) 0.0130(16) C1 0.054(2) 0.045(2) 0.040(2) 0.0104(17) 0.0118(18) 0.0031(18) C2 0.042(2) 0.040(2) 0.0364(19) 0.0030(16) 0.0138(16) 0.0002(16) C3 0.050(2) 0.040(2) 0.0324(18) 0.0003(15) 0.0115(17) 0.0022(16) C4 0.058(3) 0.046(3) 0.097(4) 0.014(2) 0.031(3) -0.008(2) C5 0.073(3) 0.046(2) 0.064(3) 0.020(2) 0.021(2) 0.015(2) C6 0.047(2) 0.048(2) 0.052(2) -0.0005(19) 0.0150(19) 0.0105(18) C7 0.061(3) 0.039(2) 0.052(2) -0.0118(18) 0.021(2) -0.0086(19) C8 0.0350(19) 0.044(2) 0.0329(18) -0.0061(16) 0.0059(15) -0.0032(16) C9 0.062(3) 0.053(3) 0.043(2) -0.0083(19) 0.013(2) -0.001(2) C10 0.056(3) 0.039(2) 0.052(2) 0.0029(19) 0.009(2) -0.0073(19) C11 0.056(3) 0.048(2) 0.037(2) 0.0009(18) 0.0163(19) 0.011(2) C12 0.045(2) 0.0315(19) 0.051(2) 0.0037(17) 0.0059(19) 0.0059(16) C13 0.045(2) 0.037(2) 0.0382(19) -0.0024(16) 0.0135(16) 0.0081(16) _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 O1 1.925(2) . ? Cu1 O3 1.974(2) . ? Cu1 N8 1.992(3) 3_656 ? Cu1 N2 2.042(3) . ? Cu1 O4 2.226(4) . ? Cu2 O1 1.925(2) . ? Cu2 O2 1.949(3) . ? Cu2 N3 1.987(4) . ? Cu2 N1 2.036(3) . ? Cu2 N6 2.284(4) . ? O1 C2 1.415(4) . ? O2 C8 1.245(5) . ? O3 C8 1.262(4) . ? O4 H4O 0.61(4) . ? O4 H4OA 0.79(5) . ? N1 C1 1.475(5) . ? N1 C5 1.489(5) . ? N1 C4 1.490(5) . ? N2 C7 1.479(5) . ? N2 C6 1.486(5) . ? N2 C3 1.487(5) . ? N3 C10 1.148(6) . ? N4 C10 1.296(6) . ? N4 C11 1.309(6) . ? N5 C11 1.142(5) . ? N6 C12 1.138(5) . ? N7 C13 1.289(5) . ? N7 C12 1.308(5) . ? N8 C13 1.142(5) . ? N8 Cu1 1.992(3) 3_656 ? C1 C2 1.512(5) . ? C1 H1 0.9700 . ? C1 H1A 0.9700 . ? C2 C3 1.512(5) . ? C2 H2 0.9800 . ? C3 H3 0.9700 . ? C3 H3A 0.9700 . ? C4 H4 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C5 H5 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C6 H6 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C7 H7 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C8 C9 1.497(5) . ? C9 H9 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O3 94.56(11) . . ? O1 Cu1 N8 164.93(13) . 3_656 ? O3 Cu1 N8 87.54(13) . 3_656 ? O1 Cu1 N2 84.90(11) . . ? O3 Cu1 N2 173.17(12) . . ? N8 Cu1 N2 91.24(13) 3_656 . ? O1 Cu1 O4 99.83(13) . . ? O3 Cu1 O4 91.12(14) . . ? N8 Cu1 O4 95.04(15) 3_656 . ? N2 Cu1 O4 95.68(14) . . ? O1 Cu2 O2 93.56(11) . . ? O1 Cu2 N3 168.10(15) . . ? O2 Cu2 N3 86.09(15) . . ? O1 Cu2 N1 85.08(12) . . ? O2 Cu2 N1 167.61(14) . . ? N3 Cu2 N1 92.72(15) . . ? O1 Cu2 N6 98.97(13) . . ? O2 Cu2 N6 94.50(15) . . ? N3 Cu2 N6 92.91(16) . . ? N1 Cu2 N6 97.87(14) . . ? C2 O1 Cu2 114.0(2) . . ? C2 O1 Cu1 114.6(2) . . ? Cu2 O1 Cu1 130.83(13) . . ? C8 O2 Cu2 137.1(3) . . ? C8 O3 Cu1 134.4(2) . . ? Cu1 O4 H4O 117(4) . . ? Cu1 O4 H4OA 124(3) . . ? H4O O4 H4OA 116(6) . . ? C1 N1 C5 109.1(3) . . ? C1 N1 C4 111.2(3) . . ? C5 N1 C4 109.5(3) . . ? C1 N1 Cu2 103.8(2) . . ? C5 N1 Cu2 113.9(3) . . ? C4 N1 Cu2 109.2(3) . . ? C7 N2 C6 108.9(3) . . ? C7 N2 C3 109.0(3) . . ? C6 N2 C3 111.2(3) . . ? C7 N2 Cu1 114.5(2) . . ? C6 N2 Cu1 108.7(2) . . ? C3 N2 Cu1 104.5(2) . . ? C10 N3 Cu2 156.7(4) . . ? C10 N4 C11 120.7(4) . . ? C12 N6 Cu2 130.2(4) . . ? C13 N7 C12 122.2(4) . . ? C13 N8 Cu1 165.1(3) . 3_656 ? N1 C1 C2 109.4(3) . . ? N1 C1 H1 109.8 . . ? C2 C1 H1 109.8 . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? H1 C1 H1A 108.2 . . ? O1 C2 C1 108.8(3) . . ? O1 C2 C3 108.4(3) . . ? C1 C2 C3 110.9(3) . . ? O1 C2 H2 109.6 . . ? C1 C2 H2 109.6 . . ? C3 C2 H2 109.6 . . ? N2 C3 C2 109.6(3) . . ? N2 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? N2 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? H3 C3 H3A 108.2 . . ? N1 C4 H4 109.5 . . ? N1 C4 H4A 109.5 . . ? H4 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C5 H5 109.5 . . ? N1 C5 H5A 109.5 . . ? H5 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C6 H6 109.5 . . ? N2 C6 H6A 109.5 . . ? H6 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C7 H7 109.5 . . ? N2 C7 H7A 109.5 . . ? H7 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O2 C8 O3 126.0(3) . . ? O2 C8 C9 116.4(3) . . ? O3 C8 C9 117.6(3) . . ? C8 C9 H9 109.5 . . ? C8 C9 H9A 109.5 . . ? H9 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C10 N4 172.7(5) . . ? N5 C11 N4 174.3(5) . . ? N6 C12 N7 173.1(4) . . ? N8 C13 N7 172.7(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.492 _refine_diff_density_min -0.611 _refine_diff_density_rms 0.096 data_complex2 _database_code_depnum_ccdc_archive 'CCDC 290151' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 Cu2 N8 O3' _chemical_formula_weight 407.35 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.184(5) _cell_length_b 8.792(2) _cell_length_c 10.887(2) _cell_angle_alpha 75.65(2) _cell_angle_beta 76.55(3) _cell_angle_gamma 74.36(3) _cell_volume 719.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 20 _exptl_crystal_description prisme _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.881 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 2.983 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_T_max 0.74 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4143 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 29.96 _reflns_number_total 4143 _reflns_number_gt 3175 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0878P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens '3 geom and 9 difmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4143 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.08146(4) 0.02543(5) 0.83250(3) 0.02898(12) Uani 1 1 d . . . Cu2 Cu 0.48458(4) -0.13481(5) 0.66614(3) 0.02918(12) Uani 1 1 d . . . O1 O 0.2440(3) -0.1232(3) 0.7396(2) 0.0301(4) Uani 1 1 d . . . O2 O 0.4930(3) 0.0595(3) 0.7206(3) 0.0435(6) Uani 1 1 d . . . O3 O 0.2608(3) 0.1043(3) 0.8747(2) 0.0401(6) Uani 1 1 d . . . N1 N -0.0916(4) -0.0991(4) 0.8264(3) 0.0386(6) Uani 1 1 d . . . N2 N 0.4576(4) -0.3044(5) 0.5834(4) 0.0439(8) Uani 1 1 d . . . N3 N -0.4053(4) 0.6829(4) 0.8272(3) 0.0475(8) Uani 1 1 d . . . N4 N -0.2376(6) 0.4541(4) 0.9563(4) 0.0610(11) Uani 1 1 d . . . N5 N -0.0917(4) 0.1853(4) 0.9205(3) 0.0373(6) Uani 1 1 d . . . N6 N 0.7124(4) -0.1272(4) 0.5502(3) 0.0455(8) Uani 1 1 d . . . N7 N 0.9520(4) -0.2080(5) 0.3807(3) 0.0568(10) Uani 1 1 d . . . N8 N 1.2037(6) -0.4320(6) 0.3962(4) 0.0782(15) Uani 1 1 d . . . C1 C 0.0061(5) -0.2498(5) 0.7838(4) 0.0436(8) Uani 1 1 d . . . C2 C 0.1659(4) -0.2161(4) 0.6908(4) 0.0373(7) Uani 1 1 d . . . C3 C 0.3024(5) -0.3627(5) 0.6622(5) 0.0501(10) Uani 1 1 d . . . C4 C 0.4085(4) 0.1214(4) 0.8152(3) 0.0323(6) Uani 1 1 d . . . C5 C 0.4894(6) 0.2248(6) 0.8614(5) 0.0531(10) Uani 1 1 d . . . H5A H 0.4011 0.2987 0.9061 0.080 Uiso 1 1 calc R . . H5B H 0.5539 0.2840 0.7890 0.080 Uiso 1 1 calc R . . H5C H 0.5653 0.1582 0.9187 0.080 Uiso 1 1 calc R . . C6 C -0.3288(4) 0.5703(4) 0.8819(3) 0.0351(7) Uani 1 1 d . . . C7 C -0.1647(4) 0.3151(4) 0.9296(3) 0.0333(6) Uani 1 1 d . . . C8 C 0.8257(4) -0.1740(4) 0.4755(3) 0.0384(7) Uani 1 1 d . . . C9 C 1.0818(5) -0.3325(5) 0.3957(3) 0.0466(9) Uani 1 1 d . . . H1N H -0.170(7) -0.033(6) 0.779(5) 0.056(13) Uiso 1 1 d . . . H1NA H -0.156(6) -0.131(6) 0.910(5) 0.061(14) Uiso 1 1 d . . . H2N H 0.536(5) -0.378(5) 0.587(4) 0.027(9) Uiso 1 1 d . . . H2NA H 0.461(7) -0.261(6) 0.502(6) 0.061(14) Uiso 1 1 d . . . H1 H -0.073(6) -0.286(5) 0.741(4) 0.041(11) Uiso 1 1 d . . . H1A H 0.046(6) -0.326(6) 0.861(5) 0.057(13) Uiso 1 1 d . . . H2 H 0.128(5) -0.151(5) 0.602(4) 0.034(10) Uiso 1 1 d . . . H3 H 0.274(6) -0.423(5) 0.607(5) 0.052(13) Uiso 1 1 d . . . H3A H 0.340(6) -0.426(6) 0.746(5) 0.058(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01970(18) 0.0383(2) 0.0263(2) -0.01136(15) 0.00210(13) -0.00292(14) Cu2 0.02137(19) 0.0379(2) 0.02395(19) -0.01093(15) 0.00080(13) 0.00086(14) O1 0.0207(9) 0.0381(12) 0.0324(11) -0.0153(9) -0.0016(8) -0.0032(8) O2 0.0341(12) 0.0489(14) 0.0473(14) -0.0229(12) 0.0146(11) -0.0151(10) O3 0.0288(11) 0.0604(16) 0.0361(12) -0.0249(12) 0.0044(9) -0.0133(11) N1 0.0267(13) 0.0532(18) 0.0355(15) -0.0092(13) -0.0026(11) -0.0104(12) N2 0.0344(15) 0.0542(19) 0.0418(18) -0.0279(15) -0.0086(13) 0.0105(14) N3 0.0449(17) 0.0541(19) 0.0377(16) -0.0099(14) -0.0152(14) 0.0062(14) N4 0.094(3) 0.0427(19) 0.0422(19) -0.0121(15) -0.0322(19) 0.0113(18) N5 0.0268(13) 0.0477(16) 0.0316(14) -0.0137(12) 0.0000(11) 0.0023(11) N6 0.0340(15) 0.0547(19) 0.0322(15) -0.0060(13) 0.0088(12) 0.0013(13) N7 0.0430(17) 0.064(2) 0.0290(15) 0.0020(14) 0.0122(13) 0.0194(15) N8 0.055(2) 0.090(3) 0.052(2) -0.011(2) 0.0012(18) 0.036(2) C1 0.0330(17) 0.052(2) 0.051(2) -0.0138(18) -0.0113(16) -0.0119(15) C2 0.0310(15) 0.0469(19) 0.0384(17) -0.0154(15) -0.0067(13) -0.0089(13) C3 0.042(2) 0.054(2) 0.062(3) -0.030(2) -0.0101(18) -0.0043(17) C4 0.0248(14) 0.0390(16) 0.0311(15) -0.0093(12) -0.0023(11) -0.0041(12) C5 0.046(2) 0.065(3) 0.059(3) -0.028(2) -0.0030(18) -0.0196(19) C6 0.0363(16) 0.0412(18) 0.0274(15) -0.0094(13) -0.0043(13) -0.0069(13) C7 0.0341(16) 0.0420(17) 0.0222(13) -0.0052(12) -0.0049(12) -0.0072(13) C8 0.0297(15) 0.0458(19) 0.0261(15) -0.0033(13) 0.0024(12) 0.0043(13) C9 0.0399(19) 0.058(2) 0.0241(15) -0.0053(15) 0.0050(13) 0.0070(16) _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 O1 1.895(2) . ? Cu1 N5 1.966(3) . ? Cu1 O3 1.966(3) . ? Cu1 N1 2.031(3) . ? Cu2 O1 1.930(2) . ? Cu2 O2 1.964(3) . ? Cu2 N6 2.001(3) . ? Cu2 N2 2.005(3) . ? Cu2 N3 2.240(3) 1_645 ? O1 C2 1.418(4) . ? O2 C4 1.257(4) . ? O3 C4 1.261(4) . ? N1 C1 1.473(5) . ? N1 H1N 0.90(5) . ? N1 H1NA 0.96(5) . ? N2 C3 1.496(6) . ? N2 H2N 0.78(4) . ? N2 H2NA 0.88(6) . ? N3 C6 1.129(5) . ? N3 Cu2 2.240(3) 1_465 ? N4 C7 1.278(5) . ? N4 C6 1.310(5) . ? N5 C7 1.153(4) . ? N6 C8 1.141(4) . ? N7 C8 1.308(4) . ? N7 C9 1.310(5) . ? N8 C9 1.136(5) . ? C1 C2 1.506(5) . ? C1 H1 1.03(4) . ? C1 H1A 0.99(5) . ? C2 C3 1.506(5) . ? C2 H2 1.07(4) . ? C3 H3 0.99(5) . ? C3 H3A 1.02(5) . ? C4 C5 1.491(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N5 177.01(11) . . ? O1 Cu1 O3 93.27(10) . . ? N5 Cu1 O3 88.12(12) . . ? O1 Cu1 N1 85.10(12) . . ? N5 Cu1 N1 94.18(13) . . ? O3 Cu1 N1 166.08(13) . . ? O1 Cu2 O2 94.49(10) . . ? O1 Cu2 N6 166.20(12) . . ? O2 Cu2 N6 89.02(13) . . ? O1 Cu2 N2 84.06(12) . . ? O2 Cu2 N2 169.40(14) . . ? N6 Cu2 N2 90.04(15) . . ? O1 Cu2 N3 97.57(12) . 1_645 ? O2 Cu2 N3 97.75(13) . 1_645 ? N6 Cu2 N3 95.17(14) . 1_645 ? N2 Cu2 N3 92.85(15) . 1_645 ? C2 O1 Cu1 112.96(19) . . ? C2 O1 Cu2 114.05(19) . . ? Cu1 O1 Cu2 131.11(12) . . ? C4 O2 Cu2 131.1(2) . . ? C4 O3 Cu1 132.7(2) . . ? C1 N1 Cu1 107.6(2) . . ? C1 N1 H1N 118(3) . . ? Cu1 N1 H1N 108(3) . . ? C1 N1 H1NA 106(3) . . ? Cu1 N1 H1NA 112(3) . . ? H1N N1 H1NA 105(4) . . ? C3 N2 Cu2 106.1(2) . . ? C3 N2 H2N 107(3) . . ? Cu2 N2 H2N 111(3) . . ? C3 N2 H2NA 121(3) . . ? Cu2 N2 H2NA 106(3) . . ? H2N N2 H2NA 106(4) . . ? C6 N3 Cu2 161.5(3) . 1_465 ? C7 N4 C6 124.1(3) . . ? C7 N5 Cu1 153.2(3) . . ? C8 N6 Cu2 152.7(4) . . ? C8 N7 C9 122.4(3) . . ? N1 C1 C2 108.1(3) . . ? N1 C1 H1 108(2) . . ? C2 C1 H1 112(2) . . ? N1 C1 H1A 107(3) . . ? C2 C1 H1A 107(3) . . ? H1 C1 H1A 116(4) . . ? O1 C2 C3 106.9(3) . . ? O1 C2 C1 109.8(3) . . ? C3 C2 C1 115.4(4) . . ? O1 C2 H2 110(2) . . ? C3 C2 H2 107(2) . . ? C1 C2 H2 108(2) . . ? N2 C3 C2 107.0(4) . . ? N2 C3 H3 104(3) . . ? C2 C3 H3 115(3) . . ? N2 C3 H3A 105(3) . . ? C2 C3 H3A 108(3) . . ? H3 C3 H3A 117(4) . . ? O2 C4 O3 125.8(3) . . ? O2 C4 C5 117.3(3) . . ? O3 C4 C5 116.9(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 N4 171.2(4) . . ? N5 C7 N4 171.2(4) . . ? N6 C8 N7 172.3(4) . . ? N8 C9 N7 172.4(5) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.616 _refine_diff_density_min -1.135 _refine_diff_density_rms 0.145 data_complex3 _database_code_depnum_ccdc_archive 'CCDC 290152' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H40 Cu4 N8 O6 S4' _chemical_formula_sum 'C22 H40 Cu4 N8 O6 S4' _chemical_formula_weight 895.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.455(4) _cell_length_b 9.114(9) _cell_length_c 12.744(8) _cell_angle_alpha 104.62(8) _cell_angle_beta 99.86(6) _cell_angle_gamma 106.10(8) _cell_volume 881.7(13) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 14 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 2.663 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details ? _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 'four cicle diffractometer' _diffrn_measurement_method '\w-2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% none _diffrn_reflns_number 5112 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 1.3370 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 29.97 _reflns_number_total 5112 _reflns_number_gt 991 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4/PC (Kretschmar, 1996)' _computing_cell_refinement CAD-4/PC _computing_data_reduction 'CFEO (Solans, 1978)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3.2 (Brueggemann & Schmid, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0061P)^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 5112 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.4170 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.0820 _refine_ls_goodness_of_fit_ref 0.799 _refine_ls_restrained_S_all 0.799 _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 0.86883(19) 0.78349(18) 0.79484(13) 0.0439(5) Uani 1 1 d . . . Cu2 Cu 1.04086(18) 0.52244(17) 0.64460(12) 0.0371(5) Uani 1 1 d . . . S1 S 1.3482(4) 0.2721(4) 0.4382(3) 0.0602(11) Uani 1 1 d . . . S2 S 0.7883(5) 1.2474(4) 1.0024(3) 0.0742(12) Uani 1 1 d . . . O1 O 1.1965(8) 0.7378(9) 0.6850(6) 0.050(3) Uani 1 1 d . . . O2 O 1.0717(9) 0.9081(8) 0.7731(6) 0.041(2) Uani 1 1 d . . . O3 O 0.8989(8) 0.5835(8) 0.7320(5) 0.0327(19) Uani 1 1 d . . . N1 N 0.9389(13) 0.2977(11) 0.6559(9) 0.048(3) Uani 1 1 d . . . N2 N 0.6775(12) 0.6571(12) 0.8467(8) 0.048(3) Uani 1 1 d . . . N3 N 1.1690(10) 0.4500(10) 0.5366(7) 0.034(3) Uani 1 1 d . . . N4 N 0.8302(14) 0.9794(13) 0.8620(9) 0.066(4) Uani 1 1 d . . . C1 C 1.0679(17) 0.2863(17) 0.7453(13) 0.137(6) Uani 1 1 d . . . H1A H 1.1039 0.3817 0.8092 0.205 Uiso 1 1 calc R . . H1B H 1.1644 0.2761 0.7177 0.205 Uiso 1 1 calc R . . H1C H 1.0191 0.1938 0.7670 0.205 Uiso 1 1 calc R . . C2 C 0.896(2) 0.1668(16) 0.5599(12) 0.141(8) Uani 1 1 d . . . H2A H 0.9968 0.1602 0.5373 0.211 Uiso 1 1 calc R . . H2B H 0.8189 0.1796 0.5007 0.211 Uiso 1 1 calc R . . H2C H 0.8412 0.0699 0.5752 0.211 Uiso 1 1 calc R . . C3 C 0.7852(15) 0.2979(15) 0.6949(10) 0.075(4) Uani 1 1 d . . . H3A H 0.7647 0.2226 0.7371 0.091 Uiso 1 1 calc R . . H3B H 0.6881 0.2611 0.6303 0.091 Uiso 1 1 calc R . . C4 C 0.7993(17) 0.4578(15) 0.7660(11) 0.062(4) Uani 1 1 d . . . H4 H 0.8673 0.4701 0.8401 0.075 Uiso 1 1 calc R . . C5 C 0.6469(15) 0.4939(16) 0.7870(11) 0.071(4) Uani 1 1 d . . . H5A H 0.5649 0.4648 0.7154 0.085 Uiso 1 1 calc R . . H5B H 0.5959 0.4272 0.8290 0.085 Uiso 1 1 calc R . . C6 C 0.7288(14) 0.6884(12) 0.9683(10) 0.084(5) Uani 1 1 d . . . H6A H 0.7275 0.7931 1.0066 0.125 Uiso 1 1 calc R . . H6B H 0.8417 0.6843 0.9892 0.125 Uiso 1 1 calc R . . H6C H 0.6508 0.6083 0.9886 0.125 Uiso 1 1 calc R . . C7 C 0.5109(15) 0.6791(14) 0.8174(9) 0.082(5) Uani 1 1 d . . . H7A H 0.5164 0.7824 0.8636 0.123 Uiso 1 1 calc R . . H7B H 0.4247 0.5960 0.8296 0.123 Uiso 1 1 calc R . . H7C H 0.4832 0.6732 0.7398 0.123 Uiso 1 1 calc R . . C8 C 1.2455(14) 0.3764(13) 0.4956(8) 0.033(3) Uani 1 1 d . . . C9 C 0.8092(17) 1.0853(16) 0.9206(11) 0.064(4) Uani 1 1 d . . . C10 C 1.1887(17) 0.8793(15) 0.7407(10) 0.040(4) Uani 1 1 d . . . C11 C 1.3530(14) 1.0151(13) 0.7563(9) 0.078(4) Uani 1 1 d . . . H11A H 1.3892 0.9978 0.6882 0.117 Uiso 1 1 calc R . . H11B H 1.4400 1.0167 0.8163 0.117 Uiso 1 1 calc R . . H11C H 1.3332 1.1161 0.7743 0.117 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 0.0491(13) 0.0361(12) 0.0496(12) 0.0121(9) 0.0195(10) 0.0164(10) Cu2 0.0439(11) 0.0321(11) 0.0393(11) 0.0125(9) 0.0145(9) 0.0154(9) S1 0.068(3) 0.052(3) 0.065(3) 0.014(2) 0.021(2) 0.030(2) S2 0.095(3) 0.063(3) 0.063(3) 0.009(2) 0.022(2) 0.032(2) O1 0.046(6) 0.039(6) 0.051(6) 0.007(5) 0.003(5) 0.004(5) O2 0.022(5) 0.032(5) 0.059(6) 0.004(4) 0.012(4) 0.002(5) O3 0.034(5) 0.028(5) 0.055(5) 0.027(4) 0.017(4) 0.022(4) N1 0.056(8) 0.032(7) 0.061(8) 0.013(6) 0.020(7) 0.023(6) N2 0.054(8) 0.041(7) 0.040(7) 0.016(6) 0.013(6) 0.026(6) N3 0.036(6) 0.039(7) 0.036(6) 0.018(5) 0.013(5) 0.018(5) N4 0.076(9) 0.050(9) 0.080(10) 0.017(7) 0.032(8) 0.028(8) C1 0.126(15) 0.154(17) 0.175(18) 0.085(15) 0.063(14) 0.072(13) C2 0.210(18) 0.068(13) 0.118(15) -0.007(11) 0.101(14) 0.004(12) C3 0.063(11) 0.061(11) 0.095(12) 0.012(9) 0.024(9) 0.020(9) C4 0.071(12) 0.041(10) 0.076(11) 0.019(9) 0.016(9) 0.023(9) C5 0.058(11) 0.084(12) 0.086(12) 0.037(10) 0.030(9) 0.031(9) C6 0.096(11) 0.049(9) 0.113(13) 0.015(9) 0.066(11) 0.022(8) C7 0.080(11) 0.113(13) 0.082(11) 0.052(10) 0.023(9) 0.056(10) C8 0.056(9) 0.035(8) 0.019(7) 0.018(6) 0.012(7) 0.024(7) C9 0.075(11) 0.051(11) 0.069(12) 0.028(9) 0.025(9) 0.016(9) C10 0.042(10) 0.027(9) 0.039(9) 0.024(8) -0.004(8) -0.011(8) C11 0.103(12) 0.074(11) 0.057(10) -0.006(8) 0.024(9) 0.052(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 O2 1.884(7) . ? Cu1 O3 1.902(6) . ? Cu1 N4 1.917(10) . ? Cu1 N2 2.024(10) . ? Cu2 O3 1.872(6) . ? Cu2 O1 1.917(8) . ? Cu2 N3 1.988(9) . ? Cu2 N1 2.042(9) . ? S1 C8 1.587(11) . ? S2 C9 1.653(14) . ? O1 C10 1.332(13) . ? O2 C10 1.203(13) . ? O3 C4 1.431(12) . ? N1 C2 1.387(13) . ? N1 C3 1.468(12) . ? N1 C1 1.482(14) . ? N2 C5 1.417(12) . ? N2 C6 1.466(12) . ? N2 C7 1.476(12) . ? N3 C8 1.149(10) . ? N4 C9 1.139(12) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.469(13) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.466(13) . ? C4 H4 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C10 C11 1.526(14) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 O2 Cu1 O3 94.4(3) . . ? O2 Cu1 N4 88.5(4) . . ? O3 Cu1 N4 176.9(4) . . ? O2 Cu1 N2 169.5(4) . . ? O3 Cu1 N2 86.4(3) . . ? N4 Cu1 N2 90.6(4) . . ? O3 Cu2 O1 93.7(3) . . ? O3 Cu2 N3 173.5(3) . . ? O1 Cu2 N3 89.2(3) . . ? O3 Cu2 N1 86.1(3) . . ? O1 Cu2 N1 157.8(4) . . ? N3 Cu2 N1 93.4(4) . . ? C10 O1 Cu2 131.8(8) . . ? C10 O2 Cu1 134.7(8) . . ? C4 O3 Cu2 114.6(7) . . ? C4 O3 Cu1 111.9(7) . . ? Cu2 O3 Cu1 133.3(4) . . ? C2 N1 C3 108.8(11) . . ? C2 N1 C1 110.1(11) . . ? C3 N1 C1 109.2(10) . . ? C2 N1 Cu2 118.0(8) . . ? C3 N1 Cu2 105.8(7) . . ? C1 N1 Cu2 104.6(8) . . ? C5 N2 C6 111.3(10) . . ? C5 N2 C7 104.3(10) . . ? C6 N2 C7 108.8(9) . . ? C5 N2 Cu1 104.6(7) . . ? C6 N2 Cu1 110.6(7) . . ? C7 N2 Cu1 117.0(8) . . ? C8 N3 Cu2 157.6(9) . . ? C9 N4 Cu1 166.0(12) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C4 112.6(11) . . ? N1 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? N1 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? O3 C4 C5 108.5(10) . . ? O3 C4 C3 111.6(11) . . ? C5 C4 C3 120.7(12) . . ? O3 C4 H4 104.8 . . ? C5 C4 H4 104.8 . . ? C3 C4 H4 104.8 . . ? N2 C5 C4 114.5(11) . . ? N2 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? N2 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 S1 179.0(11) . . ? N4 C9 S2 176.0(14) . . ? O2 C10 O1 128.6(12) . . ? O2 C10 C11 120.7(12) . . ? O1 C10 C11 110.7(12) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.654 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.118 data_complex4 _database_code_depnum_ccdc_archive 'CCDC 290153' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H8 Cu2 N4 O3 S2' _chemical_formula_sum 'C7 H8 Cu2 N4 O3 S2' _chemical_formula_weight 387.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.148(14) _cell_length_b 8.18(2) _cell_length_c 11.440(14) _cell_angle_alpha 69.38(16) _cell_angle_beta 80.36(17) _cell_angle_gamma 80.36(17) _cell_volume 699(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 16 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 3.347 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.85 _exptl_absorpt_process_details ? _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 'four cicle diffractometer' _diffrn_measurement_method '\w-2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% none _diffrn_reflns_number 3884 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.2600 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 32.76 _reflns_number_total 3884 _reflns_number_gt 1407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4/PC (Kretschmar, 1996)' _computing_cell_refinement CAD-4/PC _computing_data_reduction 'CFEO (Solans, 1978)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3.2 (Brueggemann & Schmid, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0586P)^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 3884 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2019 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 0.823 _refine_ls_restrained_S_all 0.823 _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 0.11938(11) 0.56442(11) 0.82731(8) 0.0366(3) Uani 1 1 d . B . Cu2 Cu -0.06532(11) 0.38105(11) 0.67269(8) 0.0375(3) Uani 1 1 d . B . S1 S 0.2774(3) 0.8204(3) 1.0753(2) 0.0606(7) Uani 1 1 d . . . S2 S -0.3209(3) 0.2229(3) 0.4246(2) 0.0581(6) Uani 1 1 d . . . O1 O -0.1031(7) 0.6892(7) 0.8163(5) 0.0513(15) Uani 1 1 d . . . O2 O -0.1901(6) 0.6007(7) 0.6860(5) 0.0489(14) Uani 1 1 d . . . O3 O 0.0998(5) 0.3980(6) 0.7509(4) 0.0260(10) Uani 1 1 d . . . N1 N 0.3233(8) 0.4108(9) 0.8679(6) 0.0563(19) Uani 1 1 d . . . N2 N 0.0863(9) 0.1769(9) 0.6338(7) 0.062(2) Uani 1 1 d . . . N3 N 0.1446(7) 0.7077(8) 0.9294(6) 0.0386(16) Uani 1 1 d . . . N4 N -0.2086(8) 0.3570(8) 0.5708(6) 0.0438(17) Uani 1 1 d . . . C1 C -0.2009(11) 0.7037(11) 0.7481(8) 0.044(2) Uani 1 1 d . . . C2 C -0.3423(12) 0.8437(12) 0.7475(10) 0.071(3) Uani 1 1 d . . . H2A H -0.3718 0.8501 0.8307 0.107 Uiso 1 1 calc R . . H2B H -0.4371 0.8171 0.7205 0.107 Uiso 1 1 calc R . . H2C H -0.3098 0.9546 0.6908 0.107 Uiso 1 1 calc R . . C3 C 0.2282(10) 0.1478(10) 0.6863(8) 0.055(2) Uani 1 1 d . B . H3A H 0.3235 0.1326 0.6261 0.066 Uiso 1 1 calc R A 1 H3B H 0.2278 0.0405 0.7585 0.066 Uiso 1 1 calc R A 1 C4 C 0.244(4) 0.293(4) 0.725(2) 0.033(6) Uani 0.50 1 d P B 1 H4 H 0.2991 0.3726 0.6487 0.039 Uiso 0.50 1 calc PR B 1 C4' C 0.205(4) 0.242(4) 0.778(2) 0.044(8) Uani 0.50 1 d P B 2 H4' H 0.1488 0.1629 0.8551 0.052 Uiso 0.50 1 calc PR B 2 C5 C 0.3523(10) 0.2699(10) 0.8139(8) 0.053(2) Uani 1 1 d . B . H5A H 0.4671 0.2636 0.7742 0.063 Uiso 1 1 calc R C 1 H5B H 0.3388 0.1588 0.8811 0.063 Uiso 1 1 calc R C 1 C6 C 0.2028(10) 0.7575(10) 0.9847(7) 0.045(2) Uani 1 1 d . B . C7 C -0.2553(9) 0.2964(9) 0.5166(7) 0.0350(18) Uani 1 1 d . B . 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 0.0416(6) 0.0416(6) 0.0348(6) -0.0211(5) -0.0132(5) 0.0003(5) Cu2 0.0441(6) 0.0403(6) 0.0362(6) -0.0204(5) -0.0146(5) 0.0000(5) S1 0.0670(16) 0.0705(16) 0.0541(16) -0.0266(13) -0.0157(12) -0.0134(14) S2 0.0707(16) 0.0619(15) 0.0525(16) -0.0258(12) -0.0166(12) -0.0128(13) O1 0.057(4) 0.058(4) 0.051(4) -0.033(3) -0.022(3) 0.005(3) O2 0.056(3) 0.053(3) 0.049(4) -0.027(3) -0.022(3) 0.004(3) O3 0.031(3) 0.028(2) 0.024(3) -0.013(2) -0.010(2) -0.002(2) N1 0.061(5) 0.062(5) 0.059(5) -0.035(4) -0.026(4) 0.006(4) N2 0.069(5) 0.069(5) 0.061(5) -0.038(4) -0.026(4) 0.009(4) N3 0.043(4) 0.044(4) 0.037(4) -0.023(3) -0.009(3) -0.004(3) N4 0.054(4) 0.049(4) 0.037(4) -0.020(3) -0.019(3) -0.001(4) C1 0.054(5) 0.044(5) 0.038(5) -0.019(4) -0.011(4) 0.000(4) C2 0.077(7) 0.074(7) 0.074(7) -0.039(6) -0.027(5) 0.006(6) C3 0.054(5) 0.054(5) 0.068(6) -0.030(5) -0.020(5) 0.000(4) C4 0.036(14) 0.042(16) 0.025(14) -0.020(12) -0.017(12) 0.013(11) C4' 0.07(2) 0.052(18) 0.022(14) -0.026(13) -0.021(15) 0.007(14) C5 0.056(5) 0.051(5) 0.061(6) -0.027(4) -0.024(5) 0.002(4) C6 0.053(5) 0.047(5) 0.041(5) -0.021(4) -0.013(4) 0.002(4) C7 0.037(4) 0.040(4) 0.028(5) -0.010(4) -0.005(4) -0.006(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 O3 1.897(6) . ? Cu1 N1 1.924(7) . ? Cu1 O1 1.926(7) . ? Cu1 N3 1.976(7) . ? Cu2 O3 1.783(5) . ? Cu2 N4 1.859(7) . ? Cu2 O2 1.952(7) . ? Cu2 N2 2.039(8) . ? S1 C6 1.549(9) . ? S2 C7 1.580(8) . ? O1 C1 1.170(9) . ? O2 C1 1.264(9) . ? O3 C4' 1.38(3) . ? O3 C4 1.39(3) . ? N1 C5 1.458(10) . ? N2 C3 1.340(9) . ? N3 C6 1.066(9) . ? N4 C7 1.064(8) . ? C1 C2 1.481(11) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.43(3) . ? C3 C4' 1.48(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.40(3) . ? C4 H4 0.9800 . ? C4' C5 1.41(3) . ? C4' H4' 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 N1 80.5(3) . . ? O3 Cu1 O1 99.2(3) . . ? N1 Cu1 O1 169.2(3) . . ? O3 Cu1 N3 171.6(2) . . ? N1 Cu1 N3 94.4(3) . . ? O1 Cu1 N3 84.5(3) . . ? O3 Cu2 N4 170.3(3) . . ? O3 Cu2 O2 92.4(3) . . ? N4 Cu2 O2 93.8(3) . . ? O3 Cu2 N2 86.5(3) . . ? N4 Cu2 N2 86.2(3) . . ? O2 Cu2 N2 170.7(3) . . ? C1 O1 Cu1 130.4(6) . . ? C1 O2 Cu2 140.8(5) . . ? C4' O3 C4 27.9(14) . . ? C4' O3 Cu2 108.8(14) . . ? C4 O3 Cu2 110.2(12) . . ? C4' O3 Cu1 119.3(13) . . ? C4 O3 Cu1 118.0(13) . . ? Cu2 O3 Cu1 130.3(3) . . ? C5 N1 Cu1 113.4(5) . . ? C3 N2 Cu2 109.4(6) . . ? C6 N3 Cu1 158.7(6) . . ? C7 N4 Cu2 156.6(7) . . ? O1 C1 O2 122.0(8) . . ? O1 C1 C2 114.6(7) . . ? O2 C1 C2 123.3(7) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 110.4(13) . . ? N2 C3 C4' 108.9(15) . . ? C4 C3 C4' 26.5(13) . . ? N2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C4' C3 H3A 130.9 . . ? N2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? C4' C3 H3B 86.2 . . ? H3A C3 H3B 108.1 . . ? O3 C4 C5 108.1(18) . . ? O3 C4 C3 119(2) . . ? C5 C4 C3 120(2) . . ? O3 C4 H4 102.3 . . ? C5 C4 H4 102.3 . . ? C3 C4 H4 102.3 . . ? O3 C4' C5 108(2) . . ? O3 C4' C3 116.7(18) . . ? C5 C4' C3 116(2) . . ? O3 C4' H4' 105.0 . . ? C5 C4' H4' 105.0 . . ? C3 C4' H4' 105.0 . . ? C4 C5 C4' 27.4(13) . . ? C4 C5 N1 113.2(14) . . ? C4' C5 N1 112.3(14) . . ? C4 C5 H5A 108.9 . . ? C4' C5 H5A 130.0 . . ? N1 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C4' C5 H5B 84.3 . . ? N1 C5 H5B 108.9 . . ? H5A C5 H5B 107.8 . . ? N3 C6 S1 174.9(9) . . ? N4 C7 S2 174.4(8) . . ? _diffrn_measured_fraction_theta_max 0.751 _diffrn_reflns_theta_full 32.76 _diffrn_measured_fraction_theta_full 0.751 _refine_diff_density_max 1.117 _refine_diff_density_min -0.957 _refine_diff_density_rms 0.177 data_complex5 _database_code_depnum_ccdc_archive 'CCDC 290154' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H17 Cu2 N11 O' _chemical_formula_sum 'C7 H17 Cu2 N11 O' _chemical_formula_weight 398.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 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' _cell_length_a 20.45(4) _cell_length_b 11.36(3) _cell_length_c 6.429(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1494(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 14 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 2.865 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'four cicle diffractometer' _diffrn_measurement_method '\w-2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4587 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4281 _reflns_number_gt 2856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4/PC (Kretschmar, 1996)' _computing_cell_refinement CAD-4/PC _computing_data_reduction 'CFEO (Solans, 1978)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3.2 (Brueggemann & Schmid, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.1304P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(11) _refine_ls_number_reflns 4281 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1257 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1999 _refine_ls_wR_factor_gt 0.1716 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.18768(3) 0.33308(7) 0.47740(13) 0.0336(2) Uani 1 1 d . . . Cu2 Cu 0.01013(3) 0.33322(8) 0.47688(14) 0.0371(2) Uani 1 1 d . . . O1 O 0.0983(2) 0.2888(4) 0.4051(6) 0.0316(8) Uani 1 1 d . . . N1 N -0.0195(3) 0.2183(5) 0.2595(11) 0.0382(13) Uani 1 1 d . . . N2 N 0.2174(3) 0.2116(5) 0.2672(10) 0.0371(13) Uani 1 1 d . . . N3 N 0.0419(3) 0.4400(7) 0.6980(13) 0.060(2) Uani 1 1 d . . . N5 N 0.1554(3) 0.4361(7) 0.7154(13) 0.062(2) Uani 1 1 d . . . N4 N 0.0985(4) 0.4391(5) 0.7109(10) 0.0474(14) Uani 1 1 d . . . N6 N -0.0789(3) 0.3783(8) 0.5367(16) 0.075(3) Uani 1 1 d . . . N7 N -0.0910(3) 0.4460(7) 0.6735(12) 0.0523(17) Uani 1 1 d . . . N8 N -0.1057(4) 0.5147(7) 0.7949(12) 0.066(2) Uani 1 1 d . . . N9 N 0.2762(3) 0.3435(6) 0.5916(12) 0.0523(17) Uani 1 1 d . . . N10 N 0.2923(3) 0.4293(5) 0.6742(10) 0.0389(13) Uani 1 1 d . . . N11 N 0.3132(4) 0.5122(7) 0.7475(16) 0.075(3) Uani 1 1 d . . . C1 C -0.0380(4) 0.1099(8) 0.374(2) 0.061(3) Uani 1 1 d . . . H1A H -0.0757 0.1254 0.4584 0.091 Uiso 1 1 calc R . . H1B H -0.0023 0.0854 0.4605 0.091 Uiso 1 1 calc R . . H1C H -0.0480 0.0486 0.2759 0.091 Uiso 1 1 calc R . . C2 C -0.0765(4) 0.2534(9) 0.1325(16) 0.063(2) Uani 1 1 d . . . H2A H -0.1137 0.2651 0.2214 0.095 Uiso 1 1 calc R . . H2B H -0.0861 0.1925 0.0335 0.095 Uiso 1 1 calc R . . H2C H -0.0668 0.3252 0.0602 0.095 Uiso 1 1 calc R . . C3 C 0.0382(3) 0.1986(8) 0.1279(14) 0.048(2) Uani 1 1 d . . . H3A H 0.0421 0.2622 0.0280 0.057 Uiso 1 1 calc R . . H3B H 0.0330 0.1256 0.0514 0.057 Uiso 1 1 calc R . . C4 C 0.1002(3) 0.1925(5) 0.2608(10) 0.0351(13) Uani 1 1 d . . . H4 H 0.1004 0.1183 0.3385 0.042 Uiso 1 1 calc R . . C5 C 0.1592(3) 0.1980(7) 0.1290(12) 0.0424(17) Uani 1 1 d . . . H5A H 0.1562 0.2643 0.0344 0.051 Uiso 1 1 calc R . . H5B H 0.1631 0.1266 0.0473 0.051 Uiso 1 1 calc R . . C6 C 0.2344(4) 0.1034(7) 0.3750(16) 0.050(2) Uani 1 1 d . . . H6A H 0.1978 0.0777 0.4570 0.075 Uiso 1 1 calc R . . H6B H 0.2712 0.1173 0.4641 0.075 Uiso 1 1 calc R . . H6C H 0.2452 0.0437 0.2750 0.075 Uiso 1 1 calc R . . C7 C 0.2749(4) 0.2483(9) 0.1431(15) 0.058(2) Uani 1 1 d . . . H7A H 0.2652 0.3207 0.0723 0.087 Uiso 1 1 calc R . . H7B H 0.2850 0.1884 0.0429 0.087 Uiso 1 1 calc R . . H7C H 0.3117 0.2597 0.2337 0.087 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 0.0231(3) 0.0442(4) 0.0334(4) -0.0060(5) -0.0024(3) -0.0008(3) Cu2 0.0234(3) 0.0518(5) 0.0360(4) -0.0040(6) 0.0034(3) -0.0024(3) O1 0.0234(18) 0.042(2) 0.0290(19) -0.0040(16) -0.001(2) -0.0029(19) N1 0.023(2) 0.052(3) 0.040(3) 0.000(3) -0.006(2) -0.001(2) N2 0.023(2) 0.051(3) 0.037(3) -0.003(3) 0.004(2) -0.004(2) N3 0.032(3) 0.088(5) 0.061(5) -0.034(4) 0.010(3) 0.001(3) N5 0.038(4) 0.093(6) 0.055(5) -0.037(5) -0.006(3) 0.006(4) N4 0.041(3) 0.062(4) 0.039(3) -0.018(3) -0.002(3) -0.003(3) N6 0.026(3) 0.119(6) 0.079(6) -0.037(5) 0.002(4) 0.007(3) N7 0.025(3) 0.077(4) 0.054(4) -0.005(4) 0.001(3) 0.010(3) N8 0.054(4) 0.097(6) 0.046(4) -0.011(4) 0.016(4) 0.019(4) N9 0.023(2) 0.069(4) 0.065(4) -0.020(4) -0.017(3) 0.005(3) N10 0.024(3) 0.051(3) 0.041(3) -0.009(3) -0.006(2) 0.006(2) N11 0.049(4) 0.075(5) 0.100(7) -0.048(5) 0.000(4) -0.006(4) C1 0.047(5) 0.058(5) 0.077(7) 0.001(5) 0.003(5) -0.009(4) C2 0.048(4) 0.087(6) 0.054(5) 0.009(5) -0.027(4) 0.001(4) C3 0.028(3) 0.072(6) 0.043(4) -0.005(4) 0.002(3) 0.000(3) C4 0.032(3) 0.039(3) 0.034(3) -0.006(2) 0.001(3) -0.008(3) C5 0.031(3) 0.064(5) 0.032(3) -0.011(3) 0.003(3) -0.010(3) C6 0.032(4) 0.056(5) 0.061(5) 0.000(4) 0.010(4) 0.010(3) C7 0.043(4) 0.084(6) 0.047(5) -0.001(5) 0.019(4) -0.011(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 O1 1.953(5) . ? Cu1 N9 1.957(7) . ? Cu1 N2 2.025(7) . ? Cu1 N5 2.036(7) . ? Cu1 N11 2.297(8) 2_564 ? Cu2 O1 1.928(6) . ? Cu2 N6 1.930(7) . ? Cu2 N3 1.978(8) . ? Cu2 N1 2.006(7) . ? O1 C4 1.434(7) . ? N1 C3 1.468(10) . ? N1 C2 1.479(10) . ? N1 C1 1.483(11) . ? N2 C6 1.454(10) . ? N2 C7 1.481(9) . ? N2 C5 1.493(9) . ? N3 N4 1.161(9) . ? N5 N4 1.166(9) . ? N6 N7 1.195(10) . ? N7 N8 1.144(10) . ? N9 N10 1.159(9) . ? N10 N11 1.136(9) . ? N11 Cu1 2.297(8) 2_565 ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.531(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.476(9) . ? C4 H4 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N9 166.2(3) . . ? O1 Cu1 N2 86.9(2) . . ? N9 Cu1 N2 90.8(3) . . ? O1 Cu1 N5 91.4(2) . . ? N9 Cu1 N5 89.0(3) . . ? N2 Cu1 N5 172.1(3) . . ? O1 Cu1 N11 92.1(2) . 2_564 ? N9 Cu1 N11 101.7(3) . 2_564 ? N2 Cu1 N11 95.4(3) . 2_564 ? N5 Cu1 N11 92.4(4) . 2_564 ? O1 Cu2 N6 177.6(3) . . ? O1 Cu2 N3 91.5(2) . . ? N6 Cu2 N3 90.2(3) . . ? O1 Cu2 N1 86.8(2) . . ? N6 Cu2 N1 91.5(3) . . ? N3 Cu2 N1 177.1(3) . . ? C4 O1 Cu2 112.4(4) . . ? C4 O1 Cu1 108.9(4) . . ? Cu2 O1 Cu1 138.7(2) . . ? C3 N1 C2 110.9(7) . . ? C3 N1 C1 111.3(6) . . ? C2 N1 C1 107.2(7) . . ? C3 N1 Cu2 105.0(4) . . ? C2 N1 Cu2 116.6(5) . . ? C1 N1 Cu2 105.8(6) . . ? C6 N2 C7 107.8(6) . . ? C6 N2 C5 112.8(6) . . ? C7 N2 C5 110.0(6) . . ? C6 N2 Cu1 109.3(5) . . ? C7 N2 Cu1 113.9(5) . . ? C5 N2 Cu1 103.2(4) . . ? N4 N3 Cu2 111.9(5) . . ? N4 N5 Cu1 108.8(6) . . ? N3 N4 N5 177.1(8) . . ? N7 N6 Cu2 120.9(6) . . ? N8 N7 N6 175.0(9) . . ? N10 N9 Cu1 119.1(5) . . ? N11 N10 N9 174.2(8) . . ? N10 N11 Cu1 153.9(7) . 2_565 ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C4 110.5(7) . . ? N1 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? O1 C4 C5 111.2(5) . . ? O1 C4 C3 107.7(6) . . ? C5 C4 C3 110.8(6) . . ? O1 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? C4 C5 N2 108.3(6) . . ? C4 C5 H5A 110.0 . . ? N2 C5 H5A 110.0 . . ? C4 C5 H5B 110.0 . . ? N2 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.670 _refine_diff_density_min -0.840 _refine_diff_density_rms 0.203