# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Zhi-Guo Gu' _publ_contact_author_email zhiguogu@jiangnan.edu.cn loop_ _publ_author_name 'Zhi-Guo Gu' 'Jing-Jing Na' 'Bao-Xiang Wang' 'Hongping Xiao' 'Zaijun Li' data_complex1 _database_code_depnum_ccdc_archive 'CCDC 826810' #TrackingRef '- cryatal data-complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H14 Cu2 N14' _chemical_formula_weight 397.38 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.621(3) _cell_length_b 8.204(4) _cell_length_c 11.956(5) _cell_angle_alpha 77.163(8) _cell_angle_beta 88.414(8) _cell_angle_gamma 80.874(8) _cell_volume 719.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7416 _cell_measurement_theta_min 2.151 _cell_measurement_theta_max 27.993 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.834 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 2.974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5355 _exptl_absorpt_correction_T_max 0.5739 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3588 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2504 _reflns_number_gt 2227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+0.5595P] 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 2504 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1452 _refine_ls_wR_factor_gt 0.1393 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _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 N4 N -0.2164(9) 0.4776(7) 0.6255(5) 0.0518(15) Uani 1 1 d . . . N1 N -0.3757(6) 0.3442(6) 0.4916(4) 0.0315(10) Uani 1 1 d . . . N6 N -0.0781(13) 0.6193(10) 0.7351(8) 0.106(3) Uani 1 1 d . . . Cu2 Cu -0.31137(9) 0.57991(8) 0.46833(5) 0.0326(2) Uani 1 1 d . . . N10 N -0.2570(7) 0.8064(6) 0.4732(5) 0.0431(12) Uani 1 1 d . . . N11 N -0.1210(7) 0.8467(6) 0.4351(4) 0.0363(11) Uani 1 1 d . . . N12 N 0.0078(8) 0.8951(8) 0.4008(6) 0.0636(18) Uani 1 1 d . . . Cu1 Cu 0.28857(9) 0.75148(8) 0.34584(5) 0.0338(2) Uani 1 1 d . . . C1 C 0.3733(10) 1.0511(8) 0.2026(6) 0.0543(18) Uani 1 1 d . . . H1A H 0.3670 1.1726 0.1916 0.065 Uiso 1 1 calc R . . H1B H 0.4810 1.0072 0.1669 0.065 Uiso 1 1 calc R . . C2 C 0.2161(10) 1.0121(8) 0.1495(6) 0.0541(18) Uani 1 1 d . . . H2A H 0.2203 1.0506 0.0668 0.065 Uiso 1 1 calc R . . H2B H 0.1084 1.0711 0.1766 0.065 Uiso 1 1 calc R . . C3 C 0.3138(11) 0.7301(10) 0.1026(6) 0.0584(19) Uani 1 1 d . . . H3A H 0.3460 0.6137 0.1441 0.070 Uiso 1 1 calc R . . H3B H 0.4230 0.7756 0.0814 0.070 Uiso 1 1 calc R . . C4 C 0.2143(15) 0.7320(13) -0.0064(7) 0.090(3) Uani 1 1 d . . . H4A H 0.0898 0.7313 0.0125 0.108 Uiso 1 1 calc R . . H4B H 0.2226 0.8381 -0.0601 0.108 Uiso 1 1 calc R . . C5 C 0.268(2) 0.6052(16) -0.0605(10) 0.165(7) Uani 1 1 d . . . H5A H 0.3948 0.5910 -0.0668 0.165 Uiso 1 1 d R . . H5B H 0.2153 0.6332 -0.1359 0.165 Uiso 1 1 d R . . H5C H 0.2328 0.5019 -0.0179 0.165 Uiso 1 1 d R . . N2 N -0.3520(7) 0.2671(6) 0.4127(4) 0.0416(12) Uani 1 1 d . . . N3 N -0.3383(11) 0.2026(9) 0.3380(6) 0.075(2) Uani 1 1 d . . . N5 N -0.1445(8) 0.5505(6) 0.6823(5) 0.0488(14) Uani 1 1 d . . . N7 N -0.3581(8) 0.6273(7) 0.3036(4) 0.0473(13) Uani 1 1 d . . . N8 N -0.2726(7) 0.7109(6) 0.2363(4) 0.0415(12) Uani 1 1 d . . . N9 N -0.1959(8) 0.7921(8) 0.1673(5) 0.0627(17) Uani 1 1 d . . . N13 N 0.3765(7) 0.9714(6) 0.3274(4) 0.0371(11) Uani 1 1 d . . . H13A H 0.3064 1.0391 0.3658 0.044 Uiso 1 1 calc R . . H13B H 0.4879 0.9547 0.3553 0.044 Uiso 1 1 calc R . . N14 N 0.2137(7) 0.8268(6) 0.1797(4) 0.0392(11) Uani 1 1 d . . . H14 H 0.0982 0.8122 0.1762 0.047 Uiso 1 1 d 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 N4 0.080(4) 0.036(3) 0.040(3) 0.002(2) -0.020(3) -0.023(3) N1 0.041(3) 0.021(2) 0.031(2) 0.0003(18) -0.004(2) -0.0075(19) N6 0.144(8) 0.069(5) 0.115(7) -0.018(5) -0.073(6) -0.038(5) Cu2 0.0423(5) 0.0207(4) 0.0333(4) -0.0004(3) -0.0011(3) -0.0079(3) N10 0.044(3) 0.027(3) 0.059(3) -0.009(2) 0.010(3) -0.010(2) N11 0.042(3) 0.021(2) 0.045(3) -0.010(2) 0.000(2) -0.002(2) N12 0.047(4) 0.046(3) 0.103(5) -0.022(3) 0.025(3) -0.017(3) Cu1 0.0453(5) 0.0220(4) 0.0325(4) 0.0005(3) -0.0058(3) -0.0088(3) C1 0.062(4) 0.034(3) 0.059(4) 0.011(3) 0.003(3) -0.013(3) C2 0.064(5) 0.038(4) 0.049(4) 0.016(3) -0.006(3) -0.007(3) C3 0.074(5) 0.058(4) 0.040(4) -0.012(3) -0.008(3) -0.001(4) C4 0.133(9) 0.085(7) 0.046(5) -0.015(4) -0.026(5) 0.009(6) C5 0.256(19) 0.127(12) 0.119(11) -0.047(10) -0.092(12) -0.005(13) N2 0.056(3) 0.028(3) 0.040(3) -0.003(2) -0.001(2) -0.010(2) N3 0.112(6) 0.054(4) 0.064(4) -0.019(3) -0.003(4) -0.021(4) N5 0.063(4) 0.031(3) 0.051(3) -0.003(2) -0.021(3) -0.007(3) N7 0.064(4) 0.044(3) 0.033(3) 0.000(2) -0.002(2) -0.015(3) N8 0.050(3) 0.039(3) 0.032(3) -0.002(2) -0.006(2) -0.004(3) N9 0.063(4) 0.070(4) 0.047(3) 0.008(3) 0.007(3) -0.015(3) N13 0.042(3) 0.026(2) 0.043(3) -0.005(2) -0.001(2) -0.010(2) N14 0.047(3) 0.035(3) 0.033(3) 0.000(2) -0.008(2) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N4 N5 1.193(7) . ? N4 Cu2 1.985(5) . ? N4 Cu1 1.996(5) 2_566 ? N1 N2 1.242(7) . ? N1 Cu1 2.015(5) 2_566 ? N1 Cu2 2.028(4) . ? N1 Cu2 2.429(5) 2_466 ? N6 N5 1.113(8) . ? Cu2 N7 1.952(5) . ? Cu2 N10 1.980(5) . ? Cu2 N1 2.429(5) 2_466 ? N10 N11 1.186(7) . ? N11 N12 1.148(7) . ? N12 Cu1 2.422(6) . ? Cu1 N13 1.988(5) . ? Cu1 N4 1.996(5) 2_566 ? Cu1 N14 2.015(5) . ? Cu1 N1 2.015(5) 2_566 ? C1 C2 1.481(10) . ? C1 N13 1.488(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N14 1.485(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N14 1.468(8) . ? C3 C4 1.521(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.348(14) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? N2 N3 1.130(8) . ? N7 N8 1.187(7) . ? N8 N9 1.148(7) . ? N13 H13A 0.9000 . ? N13 H13B 0.9000 . ? N14 H14 0.9100 . ? 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 N5 N4 Cu2 124.2(4) . . ? N5 N4 Cu1 133.9(5) . 2_566 ? Cu2 N4 Cu1 101.8(2) . 2_566 ? N2 N1 Cu1 124.6(4) . 2_566 ? N2 N1 Cu2 119.7(4) . . ? Cu1 N1 Cu2 99.67(19) 2_566 . ? N2 N1 Cu2 112.5(4) . 2_466 ? Cu1 N1 Cu2 98.38(18) 2_566 2_466 ? Cu2 N1 Cu2 96.87(18) . 2_466 ? N7 Cu2 N10 96.7(2) . . ? N7 Cu2 N4 163.8(3) . . ? N10 Cu2 N4 93.0(2) . . ? N7 Cu2 N1 92.2(2) . . ? N10 Cu2 N1 170.5(2) . . ? N4 Cu2 N1 79.2(2) . . ? N7 Cu2 N1 91.7(2) . 2_466 ? N10 Cu2 N1 93.08(19) . 2_466 ? N4 Cu2 N1 100.8(2) . 2_466 ? N1 Cu2 N1 83.13(18) . 2_466 ? N11 N10 Cu2 119.5(4) . . ? N12 N11 N10 175.6(6) . . ? N11 N12 Cu1 132.0(5) . . ? N13 Cu1 N4 175.1(2) . 2_566 ? N13 Cu1 N14 86.9(2) . . ? N4 Cu1 N14 97.3(2) 2_566 . ? N13 Cu1 N1 96.37(19) . 2_566 ? N4 Cu1 N1 79.2(2) 2_566 2_566 ? N14 Cu1 N1 174.57(19) . 2_566 ? N13 Cu1 N12 86.5(2) . . ? N4 Cu1 N12 95.8(2) 2_566 . ? N14 Cu1 N12 89.9(2) . . ? N1 Cu1 N12 94.6(2) 2_566 . ? C2 C1 N13 108.7(5) . . ? C2 C1 H1A 109.9 . . ? N13 C1 H1A 109.9 . . ? C2 C1 H1B 109.9 . . ? N13 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? C1 C2 N14 109.8(5) . . ? C1 C2 H2A 109.7 . . ? N14 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? N14 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? N14 C3 C4 114.5(7) . . ? N14 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? N14 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C5 C4 C3 117.4(9) . . ? C5 C4 H4A 107.9 . . ? C3 C4 H4A 107.9 . . ? C5 C4 H4B 107.9 . . ? C3 C4 H4B 107.9 . . ? H4A C4 H4B 107.2 . . ? C4 C5 H5A 108.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 110.2 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 N2 N1 176.2(7) . . ? N6 N5 N4 179.6(8) . . ? N8 N7 Cu2 121.9(4) . . ? N9 N8 N7 176.8(6) . . ? C1 N13 Cu1 107.6(4) . . ? C1 N13 H13A 110.2 . . ? Cu1 N13 H13A 110.2 . . ? C1 N13 H13B 110.2 . . ? Cu1 N13 H13B 110.2 . . ? H13A N13 H13B 108.5 . . ? C3 N14 C2 115.4(5) . . ? C3 N14 Cu1 115.0(4) . . ? C2 N14 Cu1 105.4(4) . . ? C3 N14 H14 106.9 . . ? C2 N14 H14 106.8 . . ? Cu1 N14 H14 106.9 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.788 _refine_diff_density_min -0.942 _refine_diff_density_rms 0.127 # Attachment '- cryatal data-complex 2.cif' data_complex2 _database_code_depnum_ccdc_archive 'CCDC 826811' #TrackingRef '- cryatal data-complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 Cu2 N14' _chemical_formula_weight 411.41 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.675(2) _cell_length_b 8.264(2) _cell_length_c 12.511(3) _cell_angle_alpha 104.780(4) _cell_angle_beta 90.050(5) _cell_angle_gamma 98.076(4) _cell_volume 759.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2271 _cell_measurement_theta_min 3.398 _cell_measurement_theta_max 27.183 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 2.822 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5507 _exptl_absorpt_correction_T_max 0.5887 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 3803 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2635 _reflns_number_gt 2170 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1118P)^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 2635 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1670 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.21251(9) 0.26044(8) 0.14486(5) 0.0371(3) Uani 1 1 d . . . N9 N 0.4902(7) 0.3925(8) 0.0881(6) 0.0701(18) Uani 1 1 d . . . N8 N 0.6176(6) 0.3456(6) 0.0560(4) 0.0412(11) Uani 1 1 d . . . N7 N 0.7543(6) 0.3049(6) 0.0212(4) 0.0426(12) Uani 1 1 d . . . Cu2 Cu 0.81418(8) 0.08367(8) 0.02848(5) 0.0356(3) Uani 1 1 d . . . N3 N 0.8364(10) -0.2820(9) 0.1570(5) 0.0782(19) Uani 1 1 d . . . N1 N 0.8789(6) -0.1505(5) 0.0109(4) 0.0325(10) Uani 1 1 d . . . N6 N 0.5562(12) 0.0876(10) -0.2300(7) 0.111(3) Uani 1 1 d . . . N12 N 0.7060(8) 0.3154(8) 0.3159(5) 0.0681(17) Uani 1 1 d . . . N11 N 0.7848(7) 0.2322(7) 0.2502(4) 0.0470(12) Uani 1 1 d . . . N10 N 0.8733(7) 0.1474(7) 0.1861(4) 0.0504(13) Uani 1 1 d . . . C1 C 0.1377(10) 0.5732(9) 0.2731(6) 0.068(2) Uani 1 1 d . . . H1A H 0.1459 0.6933 0.2786 0.082 Uiso 1 1 d R . . H1B H 0.0335 0.5393 0.3104 0.082 Uiso 1 1 d R . . C2 C 0.2926(11) 0.5393(9) 0.3257(7) 0.075(2) Uani 1 1 d . . . H2A H 0.2932 0.5890 0.4048 0.090 Uiso 1 1 d R . . H2B H 0.3971 0.5918 0.2972 0.090 Uiso 1 1 d R . . C3 C 0.2128(10) 0.2698(11) 0.3834(6) 0.068(2) Uani 1 1 d . . . H3A H 0.1874 0.1498 0.3478 0.081 Uiso 1 1 d R . . H3B H 0.1016 0.3105 0.4029 0.081 Uiso 1 1 d R . . C4 C 0.3208(11) 0.2926(12) 0.4854(7) 0.083(2) Uani 1 1 d . . . H4A H 0.3412 0.4121 0.5231 0.099 Uiso 1 1 d R . . H4B H 0.4343 0.2571 0.4659 0.099 Uiso 1 1 d R . . C5 C 0.2356(14) 0.1962(16) 0.5623(8) 0.101(3) Uani 1 1 d . . . H5A H 0.2917 0.2463 0.6349 0.121 Uiso 1 1 d R . . H5B H 0.1131 0.2135 0.5677 0.121 Uiso 1 1 d R . . C6 C 0.2407(15) 0.0158(15) 0.5377(10) 0.113(4) Uani 1 1 d . . . H6A H 0.1984 -0.0351 0.4628 0.169 Uiso 1 1 d R . . H6B H 0.1673 -0.0330 0.5869 0.169 Uiso 1 1 d R . . H6C H 0.3596 -0.0041 0.5462 0.169 Uiso 1 1 d R . . N2 N 0.8563(7) -0.2203(6) 0.0871(4) 0.0433(11) Uani 1 1 d . . . N4 N 0.7166(8) -0.0320(7) -0.1236(4) 0.0539(14) Uani 1 1 d . . . N5 N 0.6318(8) 0.0285(6) -0.1783(5) 0.0541(14) Uani 1 1 d . . . N13 N 0.1243(6) 0.4787(6) 0.1548(4) 0.0388(11) Uani 1 1 d . . . H13A H 0.1893 0.5378 0.1138 0.047 Uiso 1 1 d R . . H13B H 0.0117 0.4593 0.1292 0.047 Uiso 1 1 d R . . N14 N 0.2978(7) 0.3573(7) 0.3027(4) 0.0470(12) Uani 1 1 d . . . H14 H 0.4136 0.3449 0.3047 0.056 Uiso 1 1 d 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 0.0460(5) 0.0291(4) 0.0387(4) 0.0099(3) 0.0048(3) 0.0122(3) N9 0.048(3) 0.067(4) 0.113(5) 0.044(4) 0.038(3) 0.027(3) N8 0.044(3) 0.029(2) 0.056(3) 0.020(2) 0.009(2) 0.005(2) N7 0.043(3) 0.027(2) 0.064(3) 0.020(2) 0.021(2) 0.013(2) Cu2 0.0417(4) 0.0278(4) 0.0403(4) 0.0107(3) 0.0099(3) 0.0110(3) N3 0.115(6) 0.070(4) 0.066(4) 0.037(4) 0.023(4) 0.029(4) N1 0.042(2) 0.022(2) 0.035(2) 0.0089(18) 0.0104(19) 0.0096(19) N6 0.147(8) 0.075(5) 0.117(7) 0.022(5) -0.054(6) 0.041(5) N12 0.068(4) 0.068(4) 0.061(4) -0.001(3) 0.020(3) 0.022(3) N11 0.054(3) 0.046(3) 0.043(3) 0.018(2) 0.003(2) 0.005(3) N10 0.058(3) 0.048(3) 0.044(3) 0.005(2) 0.009(2) 0.018(3) C1 0.083(5) 0.050(4) 0.064(5) -0.010(3) 0.001(4) 0.029(4) C2 0.094(6) 0.046(4) 0.069(5) -0.018(4) -0.027(4) 0.021(4) C3 0.065(4) 0.085(6) 0.050(4) 0.017(4) 0.012(3) 0.002(4) C4 0.085(6) 0.091(6) 0.074(5) 0.029(5) 0.011(4) 0.001(5) C5 0.097(7) 0.145(10) 0.071(6) 0.049(6) 0.021(5) 0.011(7) C6 0.116(8) 0.114(9) 0.132(9) 0.077(8) 0.008(7) 0.012(7) N2 0.052(3) 0.036(3) 0.046(3) 0.014(2) 0.011(2) 0.013(2) N4 0.084(4) 0.034(3) 0.046(3) 0.006(2) -0.004(3) 0.025(3) N5 0.068(4) 0.034(3) 0.063(3) 0.014(3) -0.010(3) 0.015(3) N13 0.041(2) 0.026(2) 0.050(3) 0.010(2) 0.011(2) 0.007(2) N14 0.047(3) 0.055(3) 0.041(3) 0.013(2) 0.007(2) 0.015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N13 1.989(4) . ? Cu1 N4 1.991(5) 2_655 ? Cu1 N14 2.004(5) . ? Cu1 N1 2.008(4) 2_655 ? Cu1 N9 2.446(6) . ? N9 N8 1.138(7) . ? N8 N7 1.195(7) . ? N7 Cu2 1.970(4) . ? Cu2 N10 1.943(5) . ? Cu2 N4 1.991(5) . ? Cu2 N1 2.023(4) . ? Cu2 N1 2.423(5) 2_755 ? N3 N2 1.119(7) . ? N1 N2 1.235(7) . ? N1 Cu1 2.008(4) 2_655 ? N1 Cu2 2.423(5) 2_755 ? N6 N5 1.111(8) . ? N12 N11 1.159(7) . ? N11 N10 1.201(7) . ? C1 C2 1.453(10) . ? C1 N13 1.483(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N14 1.464(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.478(10) . ? C3 N14 1.485(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.494(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.450(17) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? N4 N5 1.186(7) . ? N4 Cu1 1.991(5) 2_655 ? N13 H13A 0.9000 . ? N13 H13B 0.9000 . ? N14 H14 0.9100 . ? 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 N13 Cu1 N4 174.6(2) . 2_655 ? N13 Cu1 N14 86.8(2) . . ? N4 Cu1 N14 98.1(2) 2_655 . ? N13 Cu1 N1 95.59(19) . 2_655 ? N4 Cu1 N1 79.4(2) 2_655 2_655 ? N14 Cu1 N1 176.54(19) . 2_655 ? N13 Cu1 N9 86.55(19) . . ? N4 Cu1 N9 95.9(2) 2_655 . ? N14 Cu1 N9 88.6(2) . . ? N1 Cu1 N9 94.0(2) 2_655 . ? N8 N9 Cu1 134.6(5) . . ? N9 N8 N7 176.4(6) . . ? N8 N7 Cu2 119.4(4) . . ? N10 Cu2 N7 96.2(2) . . ? N10 Cu2 N4 165.3(2) . . ? N7 Cu2 N4 93.4(2) . . ? N10 Cu2 N1 92.0(2) . . ? N7 Cu2 N1 171.36(19) . . ? N4 Cu2 N1 79.0(2) . . ? N10 Cu2 N1 90.47(19) . 2_755 ? N7 Cu2 N1 94.27(17) . 2_755 ? N4 Cu2 N1 99.9(2) . 2_755 ? N1 Cu2 N1 82.97(17) . 2_755 ? N2 N1 Cu1 123.2(4) . 2_655 ? N2 N1 Cu2 120.1(4) . . ? Cu1 N1 Cu2 99.89(19) 2_655 . ? N2 N1 Cu2 113.7(4) . 2_755 ? Cu1 N1 Cu2 97.98(18) 2_655 2_755 ? Cu2 N1 Cu2 97.03(17) . 2_755 ? N12 N11 N10 176.7(6) . . ? N11 N10 Cu2 120.6(4) . . ? C2 C1 N13 109.7(5) . . ? C2 C1 H1A 110.1 . . ? N13 C1 H1A 109.2 . . ? C2 C1 H1B 109.5 . . ? N13 C1 H1B 110.1 . . ? H1A C1 H1B 108.3 . . ? C1 C2 N14 111.1(6) . . ? C1 C2 H2A 109.7 . . ? N14 C2 H2A 110.3 . . ? C1 C2 H2B 109.0 . . ? N14 C2 H2B 108.7 . . ? H2A C2 H2B 108.0 . . ? C4 C3 N14 114.2(6) . . ? C4 C3 H3A 108.3 . . ? N14 C3 H3A 108.5 . . ? C4 C3 H3B 109.2 . . ? N14 C3 H3B 108.7 . . ? H3A C3 H3B 107.7 . . ? C3 C4 C5 112.9(8) . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4B 109.2 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 118.6(9) . . ? C6 C5 H5A 107.1 . . ? C4 C5 H5A 107.4 . . ? C6 C5 H5B 107.9 . . ? C4 C5 H5B 108.3 . . ? H5A C5 H5B 107.1 . . ? C5 C6 H6A 108.7 . . ? C5 C6 H6B 110.0 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.7 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 N2 N1 179.2(7) . . ? N5 N4 Cu2 124.9(4) . . ? N5 N4 Cu1 133.4(5) . 2_655 ? Cu2 N4 Cu1 101.6(2) . 2_655 ? N6 N5 N4 178.2(9) . . ? C1 N13 Cu1 107.1(4) . . ? C1 N13 H13A 110.6 . . ? Cu1 N13 H13A 110.3 . . ? C1 N13 H13B 110.4 . . ? Cu1 N13 H13B 110.0 . . ? H13A N13 H13B 108.5 . . ? C2 N14 C3 116.5(6) . . ? C2 N14 Cu1 105.7(4) . . ? C3 N14 Cu1 115.6(4) . . ? C2 N14 H14 106.3 . . ? C3 N14 H14 105.9 . . ? Cu1 N14 H14 106.0 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.041 _refine_diff_density_min -1.038 _refine_diff_density_rms 0.147 # Attachment '- cryatal data-complex 3.cif' data_complex3 _database_code_depnum_ccdc_archive 'CCDC 826812' #TrackingRef '- cryatal data-complex 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H18 Cu3 N22' _chemical_formula_sum 'C6 H18 Cu3 N22' _chemical_formula_weight 589.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0220(16) _cell_length_b 22.375(3) _cell_length_c 13.5792(16) _cell_angle_alpha 90.00 _cell_angle_beta 121.182(7) _cell_angle_gamma 90.00 _cell_volume 2085.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3251 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 25.36 _exptl_crystal_description Block _exptl_crystal_colour Brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.876 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1180 _exptl_absorpt_coefficient_mu 3.079 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4586 _exptl_absorpt_correction_T_max 0.5253 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10462 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.20 _reflns_number_total 3752 _reflns_number_gt 3070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXL-97 (Bruker, 2002)' _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^)+(0.0613P)^2^+1.8121P] 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 3752 _refine_ls_number_parameters 289 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.117 _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 0.20530(9) 0.98552(3) 0.52696(6) 0.03865(19) Uani 1 1 d . . . Cu2 Cu 0.63528(9) 0.94756(3) 0.63852(6) 0.04050(19) Uani 1 1 d . . . Cu3 Cu 0.70465(9) 0.87678(3) 0.92834(6) 0.0442(2) Uani 1 1 d . . . N1 N 0.6829(8) 0.9453(2) 0.8271(4) 0.0527(12) Uani 1 1 d U . . N2 N 0.7186(9) 0.9906(2) 0.8733(4) 0.0560(13) Uani 1 1 d U . . N3 N 0.7209(9) 1.0384(3) 0.9075(5) 0.0669(16) Uani 1 1 d . . . N4 N 0.3643(7) 0.9127(2) 0.5581(4) 0.0489(11) Uani 1 1 d . . . N5 N 0.3212(6) 0.8636(2) 0.5322(5) 0.0536(13) Uani 1 1 d . . . N6 N 0.2858(8) 0.8157(3) 0.5151(6) 0.0712(16) Uani 1 1 d . . . N7 N -0.0507(6) 0.94631(18) 0.4681(4) 0.0419(10) Uani 1 1 d . . . N8 N -0.0952(6) 0.8975(2) 0.4347(4) 0.0505(12) Uani 1 1 d . . . N9 N -0.1342(8) 0.8518(3) 0.4055(5) 0.0689(16) Uani 1 1 d . . . N10 N 0.4685(6) 1.02185(17) 0.6020(4) 0.0362(9) Uani 1 1 d . . . N11 N 0.5250(6) 1.0696(2) 0.6442(5) 0.0502(12) Uani 1 1 d . . . N12 N 0.5810(7) 1.1163(2) 0.6799(5) 0.0612(14) Uani 1 1 d . . . N13 N 0.8619(6) 0.99419(19) 0.6648(4) 0.0391(10) Uani 1 1 d . . . N14 N 1.0212(7) 0.9841(2) 0.7313(5) 0.0594(15) Uani 1 1 d . . . N15 N 1.1730(9) 0.9755(3) 0.7989(5) 0.0715(17) Uani 1 1 d . . . N16 N 0.7557(8) 0.8698(2) 0.6549(5) 0.0577(13) Uani 1 1 d . A . N17 N 0.8992(7) 0.8535(2) 0.7130(5) 0.0585(14) Uani 1 1 d D . . N18 N 0.9820(16) 0.8221(4) 0.7896(8) 0.051(2) Uani 0.50 1 d PD A 1 N18' N 1.0728(13) 0.8500(6) 0.7495(11) 0.087(5) Uani 0.50 1 d PD A 2 N19 N 0.9833(8) 0.8642(2) 0.9830(5) 0.0610(14) Uani 1 1 d . . . H19A H 0.9998 0.8658 0.9224 0.073 Uiso 1 1 d R . . H19B H 1.0532 0.8940 1.0313 0.073 Uiso 1 1 d R . . N20 N 0.6061(10) 0.9180(3) 1.0205(5) 0.0742(18) Uani 1 1 d D . . H20A H 0.6802 0.9503 1.0558 0.089 Uiso 1 1 d R . . H20B H 0.4830 0.9305 0.9730 0.089 Uiso 1 1 d R . . N21 N 0.4855(6) 0.8283(2) 0.7944(5) 0.0565(14) Uani 1 1 d D . . H21A H 0.3706 0.8470 0.7672 0.068 Uiso 1 1 d R . . H21B H 0.5093 0.8252 0.7367 0.068 Uiso 1 1 d R . . N22 N 0.7397(7) 0.8035(2) 1.0286(5) 0.0565(13) Uani 1 1 d . . . C1 C 0.6110(12) 0.8806(3) 1.1007(6) 0.0681(19) Uani 1 1 d D . . H1A H 0.4773 0.8738 1.0801 0.082 Uiso 1 1 d R . . H1B H 0.6746 0.9018 1.1735 0.082 Uiso 1 1 d R . . C2 C 0.7091(10) 0.8198(3) 1.1214(6) 0.0634(17) Uani 1 1 d . . . H2A H 0.8209 0.8242 1.2006 0.076 Uiso 1 1 d R . . H2B H 0.6132 0.7949 1.1309 0.076 Uiso 1 1 d R . . C3 C 0.4773(9) 0.7731(3) 0.8327(5) 0.0578(16) Uani 1 1 d D . . H3A H 0.4975 0.7445 0.7860 0.069 Uiso 1 1 d R . . H3B H 0.3449 0.7674 0.8153 0.069 Uiso 1 1 d R . . C4 C 0.6130(10) 0.7552(3) 0.9583(6) 0.0639(17) Uani 1 1 d . . . H4A H 0.5168 0.7410 0.9807 0.077 Uiso 1 1 d R . . H4B H 0.6734 0.7179 0.9534 0.077 Uiso 1 1 d R . . C5 C 1.0533(10) 0.8111(3) 1.0381(7) 0.0700(19) Uani 1 1 d . . . H5A H 1.1862 0.8172 1.1008 0.084 Uiso 1 1 d R . . H5B H 1.0578 0.7834 0.9846 0.084 Uiso 1 1 d R . . C6 C 0.9415(9) 0.7815(3) 1.0869(6) 0.0625(17) Uani 1 1 d . . . H6A H 0.9715 0.7358 1.0806 0.075 Uiso 1 1 d R . . H6B H 1.0387 0.7861 1.1754 0.075 Uiso 1 1 d 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 0.0412(4) 0.0272(3) 0.0470(4) -0.0035(3) 0.0224(3) -0.0024(2) Cu2 0.0329(3) 0.0368(3) 0.0568(4) 0.0049(3) 0.0268(3) 0.0068(3) Cu3 0.0348(3) 0.0464(4) 0.0449(4) 0.0134(3) 0.0160(3) -0.0068(3) N1 0.073(3) 0.040(2) 0.055(3) 0.0111(19) 0.040(3) -0.007(2) N2 0.087(4) 0.058(3) 0.045(3) -0.008(2) 0.050(3) -0.022(3) N3 0.091(4) 0.064(4) 0.055(3) -0.020(3) 0.044(3) -0.031(3) N4 0.043(3) 0.043(3) 0.067(3) 0.004(2) 0.033(2) 0.004(2) N5 0.027(2) 0.042(3) 0.084(4) -0.030(3) 0.023(2) 0.002(2) N6 0.052(3) 0.072(4) 0.085(4) -0.026(3) 0.032(3) -0.015(3) N7 0.042(2) 0.032(2) 0.064(3) -0.009(2) 0.036(2) -0.0045(19) N8 0.034(2) 0.041(3) 0.051(3) -0.012(2) 0.005(2) 0.002(2) N9 0.049(3) 0.060(4) 0.085(4) -0.011(3) 0.026(3) 0.011(3) N10 0.027(2) 0.026(2) 0.052(3) -0.0060(19) 0.0179(19) -0.0044(16) N11 0.037(2) 0.047(3) 0.065(3) -0.009(3) 0.026(2) -0.005(2) N12 0.041(3) 0.058(3) 0.071(4) -0.021(3) 0.019(3) 0.007(2) N13 0.027(2) 0.047(2) 0.038(2) 0.0135(19) 0.013(2) 0.0028(18) N14 0.033(3) 0.063(3) 0.069(4) 0.035(3) 0.017(3) -0.002(2) N15 0.065(4) 0.080(4) 0.068(4) 0.033(3) 0.033(3) -0.003(3) N16 0.054(3) 0.046(3) 0.075(4) 0.012(3) 0.034(3) 0.017(2) N17 0.032(3) 0.058(3) 0.064(3) -0.018(3) 0.010(3) 0.010(2) N18 0.057(6) 0.056(6) 0.047(6) 0.016(5) 0.031(5) 0.024(5) N18' 0.074(9) 0.073(8) 0.065(8) -0.031(7) 0.002(7) 0.030(7) N19 0.064(3) 0.044(3) 0.071(4) 0.009(3) 0.033(3) -0.012(2) N20 0.110(5) 0.065(3) 0.083(4) 0.031(3) 0.075(4) 0.045(3) N21 0.026(2) 0.060(3) 0.073(3) 0.027(3) 0.018(2) -0.014(2) N22 0.054(3) 0.044(3) 0.074(4) 0.015(3) 0.035(3) 0.000(2) C1 0.094(5) 0.059(4) 0.073(4) 0.018(3) 0.059(4) 0.025(4) C2 0.068(4) 0.066(4) 0.068(4) 0.018(3) 0.044(4) 0.002(3) C3 0.049(3) 0.058(4) 0.056(4) 0.005(3) 0.020(3) -0.010(3) C4 0.058(4) 0.066(4) 0.065(4) 0.012(3) 0.029(3) 0.016(3) C5 0.059(4) 0.067(4) 0.079(5) 0.001(4) 0.032(4) 0.013(3) C6 0.060(4) 0.069(4) 0.059(4) -0.007(3) 0.031(3) -0.019(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.976(5) . ? Cu1 N7 1.981(4) . ? Cu1 N10 1.982(4) . ? Cu1 N7 1.989(4) 3_576 ? Cu1 N13 2.413(4) 3_676 ? Cu1 Cu1 3.0510(14) 3_576 ? Cu2 N16 1.947(5) . ? Cu2 N13 1.962(4) . ? Cu2 N4 2.017(5) . ? Cu2 N10 2.028(4) . ? Cu2 N1 2.386(5) . ? Cu3 N19 1.977(6) . ? Cu3 N1 2.005(4) . ? Cu3 N20 2.017(5) . ? Cu3 N22 2.055(5) . ? Cu3 N21 2.065(5) . ? N1 N2 1.149(7) . ? N2 N3 1.161(7) . ? N4 N5 1.149(6) . ? N5 N6 1.103(7) . ? N7 N8 1.165(6) . ? N7 Cu1 1.989(4) 3_576 ? N8 N9 1.083(7) . ? N10 N11 1.185(6) . ? N11 N12 1.143(7) . ? N13 N14 1.142(7) . ? N13 Cu1 2.413(4) 3_676 ? N14 N15 1.098(8) . ? N16 N17 1.067(7) . ? N17 N18 1.141(7) . ? N17 N18' 1.216(9) . ? N19 C5 1.361(8) . ? N19 H19A 0.8999 . ? N19 H19B 0.9001 . ? N20 C1 1.358(6) . ? N20 H20A 0.9000 . ? N20 H20B 0.9000 . ? N21 C3 1.356(6) . ? N21 H21A 0.8999 . ? N21 H21B 0.9000 . ? N22 C2 1.450(9) . ? N22 C4 1.452(9) . ? N22 C6 1.471(8) . ? C1 C2 1.523(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9699 . ? C2 H2A 0.9862 . ? C2 H2B 1.0106 . ? C3 C4 1.526(9) . ? C3 H3A 0.9701 . ? C3 H3B 0.9700 . ? C4 H4A 1.0168 . ? C4 H4B 0.9843 . ? C5 C6 1.514(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 1.0637 . ? C6 H6B 1.0459 . ? 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 N4 Cu1 N7 98.08(19) . . ? N4 Cu1 N10 80.24(18) . . ? N7 Cu1 N10 174.0(2) . . ? N4 Cu1 N7 166.0(2) . 3_576 ? N7 Cu1 N7 79.57(18) . 3_576 ? N10 Cu1 N7 100.66(17) . 3_576 ? N4 Cu1 N13 98.33(18) . 3_676 ? N7 Cu1 N13 92.42(17) . 3_676 ? N10 Cu1 N13 93.50(17) . 3_676 ? N7 Cu1 N13 95.57(18) 3_576 3_676 ? N4 Cu1 Cu1 136.37(14) . 3_576 ? N7 Cu1 Cu1 39.88(12) . 3_576 ? N10 Cu1 Cu1 140.03(12) . 3_576 ? N7 Cu1 Cu1 39.69(12) 3_576 3_576 ? N13 Cu1 Cu1 95.21(10) 3_676 3_576 ? N16 Cu2 N13 95.5(2) . . ? N16 Cu2 N4 92.7(2) . . ? N13 Cu2 N4 160.31(19) . . ? N16 Cu2 N10 170.5(2) . . ? N13 Cu2 N10 92.33(17) . . ? N4 Cu2 N10 78.18(17) . . ? N16 Cu2 N1 93.7(2) . . ? N13 Cu2 N1 101.41(18) . . ? N4 Cu2 N1 95.84(19) . . ? N10 Cu2 N1 89.92(18) . . ? N19 Cu3 N1 92.7(2) . . ? N19 Cu3 N20 124.2(3) . . ? N1 Cu3 N20 98.8(2) . . ? N19 Cu3 N22 84.1(2) . . ? N1 Cu3 N22 175.8(2) . . ? N20 Cu3 N22 85.2(2) . . ? N19 Cu3 N21 122.5(2) . . ? N1 Cu3 N21 93.74(19) . . ? N20 Cu3 N21 111.0(3) . . ? N22 Cu3 N21 85.8(2) . . ? N2 N1 Cu3 113.1(4) . . ? N2 N1 Cu2 115.1(4) . . ? Cu3 N1 Cu2 131.4(2) . . ? N1 N2 N3 168.2(8) . . ? N5 N4 Cu1 131.5(4) . . ? N5 N4 Cu2 127.2(4) . . ? Cu1 N4 Cu2 101.1(2) . . ? N6 N5 N4 175.2(8) . . ? N8 N7 Cu1 128.1(4) . . ? N8 N7 Cu1 131.4(4) . 3_576 ? Cu1 N7 Cu1 100.43(18) . 3_576 ? N9 N8 N7 178.8(7) . . ? N11 N10 Cu1 131.1(4) . . ? N11 N10 Cu2 125.5(4) . . ? Cu1 N10 Cu2 100.48(17) . . ? N12 N11 N10 176.2(7) . . ? N14 N13 Cu2 126.2(4) . . ? N14 N13 Cu1 115.1(4) . 3_676 ? Cu2 N13 Cu1 103.63(18) . 3_676 ? N15 N14 N13 176.8(8) . . ? N17 N16 Cu2 132.1(5) . . ? N16 N17 N18 141.3(9) . . ? N16 N17 N18' 153.2(11) . . ? N18 N17 N18' 65.5(9) . . ? C5 N19 Cu3 113.3(4) . . ? C5 N19 H19A 108.9 . . ? Cu3 N19 H19A 108.9 . . ? C5 N19 H19B 108.9 . . ? Cu3 N19 H19B 109.0 . . ? H19A N19 H19B 107.8 . . ? C1 N20 Cu3 111.0(4) . . ? C1 N20 H20A 109.4 . . ? Cu3 N20 H20A 109.5 . . ? C1 N20 H20B 109.3 . . ? Cu3 N20 H20B 109.6 . . ? H20A N20 H20B 108.0 . . ? C3 N21 Cu3 109.2(4) . . ? C3 N21 H21A 109.8 . . ? Cu3 N21 H21A 109.9 . . ? C3 N21 H21B 109.7 . . ? Cu3 N21 H21B 109.9 . . ? H21A N21 H21B 108.3 . . ? C2 N22 C4 112.5(5) . . ? C2 N22 C6 104.5(5) . . ? C4 N22 C6 107.8(5) . . ? C2 N22 Cu3 110.4(4) . . ? C4 N22 Cu3 110.4(4) . . ? C6 N22 Cu3 111.0(4) . . ? N20 C1 C2 119.7(6) . . ? N20 C1 H1A 107.3 . . ? C2 C1 H1A 107.6 . . ? N20 C1 H1B 107.3 . . ? C2 C1 H1B 107.4 . . ? H1A C1 H1B 106.9 . . ? N22 C2 C1 111.6(5) . . ? N22 C2 H2A 120.4 . . ? C1 C2 H2A 101.7 . . ? N22 C2 H2B 117.1 . . ? C1 C2 H2B 99.3 . . ? H2A C2 H2B 103.8 . . ? N21 C3 C4 121.2(6) . . ? N21 C3 H3A 107.0 . . ? C4 C3 H3A 107.1 . . ? N21 C3 H3B 106.9 . . ? C4 C3 H3B 107.2 . . ? H3A C3 H3B 106.7 . . ? N22 C4 C3 113.0(5) . . ? N22 C4 H4A 114.6 . . ? C3 C4 H4A 101.8 . . ? N22 C4 H4B 118.3 . . ? C3 C4 H4B 103.7 . . ? H4A C4 H4B 103.4 . . ? N19 C5 C6 116.9(6) . . ? N19 C5 H5A 108.2 . . ? C6 C5 H5A 108.0 . . ? N19 C5 H5B 108.1 . . ? C6 C5 H5B 108.0 . . ? H5A C5 H5B 107.3 . . ? N22 C6 C5 110.8(6) . . ? N22 C6 H6A 120.7 . . ? C5 C6 H6A 100.1 . . ? N22 C6 H6B 122.9 . . ? C5 C6 H6B 101.7 . . ? H6A C6 H6B 97.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.836 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.091