# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1229am _database_code_depnum_ccdc_archive 'CCDC 855746' #TrackingRef 'ladder.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 Cu N3' _chemical_formula_sum 'C8 H6 Cu N3' _chemical_formula_weight 207.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.9638(15) _cell_length_b 12.926(3) _cell_length_c 9.457(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.710(5) _cell_angle_gamma 90.00 _cell_volume 728.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 432 _cell_measurement_theta_min 2.665 _cell_measurement_theta_max 23.150 _exptl_crystal_description sheet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.894 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 2.930 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4735 _exptl_absorpt_correction_T_max 0.6676 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1793 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1200 _reflns_number_gt 906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1717P)^2^+0.2667P] 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 1200 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.2326 _refine_ls_wR_factor_gt 0.1556 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.13322(13) 0.94209(8) 0.72315(10) 0.0366(5) Uani 1 1 d . . . N1 N 0.4481(10) 0.9773(5) 0.7239(7) 0.0312(14) Uani 1 1 d . . . C3 C 0.6306(11) 0.9372(5) 0.6645(8) 0.0282(17) Uani 1 1 d . . . C8 C 0.8160(11) 0.8348(5) 0.4792(8) 0.0322(17) Uani 1 1 d . . . H8A H 0.9473 0.8729 0.4943 0.039 Uiso 1 1 calc R . . C1 C 0.5303(15) 1.0509(6) 0.8158(9) 0.040(2) Uani 1 1 d . . . H1A H 0.4448 1.0911 0.8745 0.048 Uiso 1 1 calc R . . C4 C 0.6274(12) 0.8559(6) 0.5571(8) 0.0297(16) Uani 1 1 d . . . N2 N 0.8224(9) 0.9838(5) 0.7127(7) 0.0312(14) Uani 1 1 d . . . C2 C 0.7528(14) 1.0559(5) 0.8082(10) 0.039(2) Uani 1 1 d . . . H2A H 0.8464 1.1012 0.8595 0.047 Uiso 1 1 calc R . . C6 C 0.4435(12) 0.7197(6) 0.4220(8) 0.0384(19) Uani 1 1 d . . . H6A H 0.3154 0.6797 0.4052 0.046 Uiso 1 1 calc R . . C7 C 0.8040(12) 0.7578(6) 0.3812(8) 0.0377(18) Uani 1 1 d . . . H7A H 0.9324 0.7446 0.3321 0.045 Uiso 1 1 calc R . . C5 C 0.4358(12) 0.7991(6) 0.5238(8) 0.0353(18) Uani 1 1 d . . . H5A H 0.3032 0.8131 0.5681 0.042 Uiso 1 1 calc R . . N3 N 0.6210(10) 0.6986(5) 0.3490(7) 0.0374(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0171(7) 0.0539(9) 0.0392(8) -0.0056(4) 0.0045(5) -0.0009(3) N1 0.020(3) 0.042(3) 0.032(3) -0.002(3) 0.004(3) -0.003(3) C3 0.014(4) 0.041(4) 0.030(4) 0.005(3) 0.006(3) 0.001(3) C8 0.024(4) 0.029(4) 0.044(4) 0.001(3) 0.005(3) 0.001(3) C1 0.036(5) 0.045(5) 0.040(5) -0.013(4) 0.005(4) 0.004(3) C4 0.029(4) 0.032(4) 0.028(4) 0.004(3) 0.002(3) 0.008(3) N2 0.019(3) 0.037(3) 0.038(4) -0.003(3) 0.004(3) -0.001(3) C2 0.034(5) 0.034(4) 0.049(5) -0.010(4) 0.000(4) -0.003(3) C6 0.025(4) 0.046(5) 0.044(5) -0.008(4) 0.004(3) -0.001(3) C7 0.019(4) 0.053(5) 0.042(5) -0.006(4) 0.008(3) 0.002(3) C5 0.030(4) 0.040(4) 0.037(4) -0.005(4) 0.006(3) -0.001(3) N3 0.029(3) 0.047(4) 0.037(4) -0.005(3) 0.002(3) 0.002(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 N2 1.929(6) 1_455 ? Cu1 N1 1.932(6) . ? Cu1 N3 2.177(7) 4_576 ? N1 C3 1.351(9) . ? N1 C1 1.364(10) . ? C3 N2 1.353(9) . ? C3 C4 1.461(10) . ? C8 C7 1.359(10) . ? C8 C4 1.400(9) . ? C8 H8A 0.9300 . ? C1 C2 1.334(12) . ? C1 H1A 0.9300 . ? C4 C5 1.382(10) . ? N2 C2 1.375(10) . ? N2 Cu1 1.929(6) 1_655 ? C2 H2A 0.9300 . ? C6 N3 1.319(9) . ? C6 C5 1.410(11) . ? C6 H6A 0.9300 . ? C7 N3 1.356(9) . ? C7 H7A 0.9300 . ? C5 H5A 0.9300 . ? N3 Cu1 2.177(7) 4_675 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 150.0(3) 1_455 . ? N2 Cu1 N3 101.8(3) 1_455 4_576 ? N1 Cu1 N3 104.6(2) . 4_576 ? C3 N1 C1 105.1(6) . . ? C3 N1 Cu1 135.2(5) . . ? C1 N1 Cu1 119.1(5) . . ? N1 C3 N2 111.9(7) . . ? N1 C3 C4 125.5(6) . . ? N2 C3 C4 122.5(6) . . ? C7 C8 C4 118.9(7) . . ? C7 C8 H8A 120.5 . . ? C4 C8 H8A 120.5 . . ? C2 C1 N1 109.1(7) . . ? C2 C1 H1A 125.4 . . ? N1 C1 H1A 125.4 . . ? C5 C4 C8 116.9(7) . . ? C5 C4 C3 121.6(6) . . ? C8 C4 C3 121.4(6) . . ? C3 N2 C2 104.3(6) . . ? C3 N2 Cu1 133.4(5) . 1_655 ? C2 N2 Cu1 118.4(5) . 1_655 ? C1 C2 N2 109.5(7) . . ? C1 C2 H2A 125.2 . . ? N2 C2 H2A 125.2 . . ? N3 C6 C5 124.1(7) . . ? N3 C6 H6A 118.0 . . ? C5 C6 H6A 118.0 . . ? N3 C7 C8 125.6(6) . . ? N3 C7 H7A 117.2 . . ? C8 C7 H7A 117.2 . . ? C4 C5 C6 119.3(6) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? C6 N3 C7 115.0(7) . . ? C6 N3 Cu1 120.5(5) . 4_675 ? C7 N3 Cu1 123.2(5) . 4_675 ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 1.285 _refine_diff_density_min -0.802 _refine_diff_density_rms 0.261 data_5 _database_code_depnum_ccdc_archive 'CCDC 855747' #TrackingRef 'tube.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 Cu2 N4 S' _chemical_formula_sum 'C7 H4 Cu2 N4 S' _chemical_formula_weight 303.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4(2)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z+1/2' 'y, -x, z+1/2' '-x, -y, -z' 'x, y, -z' 'y, -x, -z-1/2' '-y, x, -z-1/2' _cell_length_a 12.3244(2) _cell_length_b 12.3244(2) _cell_length_c 5.9519(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 904.04(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1782 _cell_measurement_theta_min 3.5834 _cell_measurement_theta_max 71.4524 _exptl_crystal_description square _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 7.625 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1504 _exptl_absorpt_correction_T_max 0.3108 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4098 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1747 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 71.59 _reflns_number_total 937 _reflns_number_gt 796 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXS-97 _computing_publication_material SHELXS-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+34.2056P] 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 SHELXL _refine_ls_extinction_coef 0.0024(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 937 _refine_ls_number_parameters 98 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0905 _refine_ls_wR_factor_ref 0.2168 _refine_ls_wR_factor_gt 0.2143 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.082 _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 0.34097(18) 0.12619(19) 0.0000 0.0269(7) Uani 1 2 d SU . . Cu2 Cu 0.1364(3) 0.0247(3) 0.1267(7) 0.0266(9) Uani 0.50 1 d PU . 1 N1 N 0.2455(7) 0.0545(7) 0.3843(19) 0.029(2) Uani 0.50 1 d PU . 1 S1 S 0.1306(4) 0.0231(4) 0.2497(11) 0.0180(11) Uani 0.50 1 d PU . 2 C1 C 0.2455(7) 0.0545(7) 0.3843(19) 0.029(2) Uani 0.50 1 d PU . 2 N2 N 0.3437(7) 0.0921(7) 0.3182(15) 0.0250(19) Uani 1 1 d U . . C2 C 0.3990(11) 0.1159(12) 0.5000 0.021(3) Uani 1 2 d SU . . C3 C 0.5107(11) 0.1595(12) 0.5000 0.023(3) Uani 1 2 d SU . . N4 N 0.7155(12) 0.2532(12) 0.5000 0.036(3) Uani 1 2 d SU . . C4 C 0.5782(16) 0.1540(18) 0.683(4) 0.023(4) Uani 0.50 1 d PU . 1 H4A H 0.5555 0.1175 0.8118 0.028 Uiso 0.50 1 calc PR . 1 C5 C 0.6783(17) 0.2016(19) 0.679(4) 0.025(4) Uani 0.50 1 d PU . 1 H5A H 0.7217 0.1976 0.8069 0.030 Uiso 0.50 1 calc PR . 1 C4' C 0.552(2) 0.212(2) 0.687(5) 0.042(6) Uani 0.50 1 d PU . 2 H4'A H 0.5114 0.2144 0.8180 0.050 Uiso 0.50 1 calc PR . 2 C5' C 0.655(2) 0.261(2) 0.681(5) 0.039(6) Uani 0.50 1 d PU . 2 H5'A H 0.6799 0.2992 0.8056 0.046 Uiso 0.50 1 calc PR . 2 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 0.0284(13) 0.0363(14) 0.0161(11) 0.000 0.000 -0.0066(10) Cu2 0.0285(18) 0.041(2) 0.0102(19) -0.0038(16) -0.0024(16) -0.0048(14) N1 0.027(4) 0.027(4) 0.034(5) 0.002(4) -0.003(4) -0.001(3) S1 0.020(2) 0.025(2) 0.009(2) 0.000(2) -0.001(2) -0.0020(17) C1 0.027(4) 0.027(4) 0.034(5) 0.002(4) -0.003(4) -0.001(3) N2 0.023(4) 0.028(4) 0.025(4) 0.014(4) -0.003(4) -0.004(3) C2 0.018(5) 0.027(6) 0.019(6) 0.000 0.000 -0.002(5) C3 0.022(6) 0.025(6) 0.023(6) 0.000 0.000 -0.003(5) N4 0.036(6) 0.043(6) 0.028(6) 0.000 0.000 -0.002(5) C4 0.022(7) 0.027(8) 0.020(8) 0.002(7) -0.003(7) -0.001(6) C5 0.028(8) 0.031(8) 0.016(8) 0.001(7) -0.005(7) -0.004(7) C4' 0.039(9) 0.047(9) 0.039(10) -0.003(8) 0.006(8) -0.007(8) C5' 0.041(9) 0.048(9) 0.027(9) -0.002(8) 0.004(8) -0.006(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.940(9) 6 ? Cu1 N2 1.940(9) . ? Cu1 N4 2.231(15) 7_566 ? Cu1 Cu2 2.914(4) 6 ? Cu1 Cu2 2.914(4) . ? Cu2 Cu2 1.508(8) 6 ? Cu2 N1 2.072(11) . ? Cu2 Cu2 2.827(6) 8_556 ? Cu2 Cu2 2.827(6) 7_556 ? N1 N2 1.355(12) . ? N1 N1 1.38(2) 6_556 ? S1 S1 2.311(7) 7_556 ? S1 S1 2.311(7) 8_556 ? N2 C2 1.312(12) . ? C2 N2 1.312(12) 6_556 ? C2 C3 1.478(19) . ? C3 C4 1.37(2) . ? C3 C4 1.37(2) 6_556 ? C3 C4' 1.38(3) . ? C3 C4' 1.38(3) 6_556 ? N4 C5' 1.32(3) . ? N4 C5' 1.32(3) 6_556 ? N4 C5 1.32(2) . ? N4 C5 1.32(2) 6_556 ? N4 Cu1 2.231(15) 3_655 ? C4 C5 1.37(3) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C4' C5' 1.40(3) . ? C4' H4'A 0.9300 . ? C5' H5'A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N2 154.9(5) 6 . ? N2 Cu1 N4 101.4(3) 6 7_566 ? N2 Cu1 N4 101.4(3) . 7_566 ? N2 Cu1 Cu2 70.7(3) 6 6 ? N2 Cu1 Cu2 100.1(3) . 6 ? N4 Cu1 Cu2 87.5(4) 7_566 6 ? N2 Cu1 Cu2 100.1(3) 6 . ? N2 Cu1 Cu2 70.7(3) . . ? N4 Cu1 Cu2 87.5(4) 7_566 . ? Cu2 Cu1 Cu2 30.01(16) 6 . ? Cu2 Cu2 N1 137.7(3) 6 . ? Cu2 Cu2 Cu2 121.27(15) 6 8_556 ? N1 Cu2 Cu2 89.2(3) . 8_556 ? Cu2 Cu2 Cu2 121.27(15) 6 7_556 ? N1 Cu2 Cu2 93.2(4) . 7_556 ? Cu2 Cu2 Cu2 74.37(13) 8_556 7_556 ? Cu2 Cu2 Cu1 75.00(8) 6 . ? N1 Cu2 Cu1 63.5(3) . . ? Cu2 Cu2 Cu1 122.23(17) 8_556 . ? Cu2 Cu2 Cu1 149.00(19) 7_556 . ? N2 N1 N1 106.9(6) . 6_556 ? N2 N1 Cu2 115.2(8) . . ? N1 N1 Cu2 137.7(3) 6_556 . ? S1 S1 S1 90.000(1) 7_556 8_556 ? C2 N2 N1 107.5(9) . . ? C2 N2 Cu1 140.0(7) . . ? N1 N2 Cu1 110.0(7) . . ? N2 C2 N2 111.1(12) . 6_556 ? N2 C2 C3 124.4(6) . . ? N2 C2 C3 124.4(6) 6_556 . ? C4 C3 C4 105(2) . 6_556 ? C4 C3 C4' 32.9(12) . . ? C4 C3 C4' 115.9(16) 6_556 . ? C4 C3 C4' 115.9(16) . 6_556 ? C4 C3 C4' 32.9(12) 6_556 6_556 ? C4' C3 C4' 107(2) . 6_556 ? C4 C3 C2 123.1(11) . . ? C4 C3 C2 123.1(11) 6_556 . ? C4' C3 C2 121.0(13) . . ? C4' C3 C2 121.0(13) 6_556 . ? C5' N4 C5' 110(2) . 6_556 ? C5' N4 C5 34.7(13) . . ? C5' N4 C5 119.9(17) 6_556 . ? C5' N4 C5 119.9(17) . 6_556 ? C5' N4 C5 34.7(13) 6_556 6_556 ? C5 N4 C5 107(2) . 6_556 ? C5' N4 Cu1 117.5(13) . 3_655 ? C5' N4 Cu1 117.5(13) 6_556 3_655 ? C5 N4 Cu1 122.4(11) . 3_655 ? C5 N4 Cu1 122.4(11) 6_556 3_655 ? C5 C4 C3 121(2) . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.6 . . ? N4 C5 C4 122(2) . . ? N4 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C3 C4' C5' 121(2) . . ? C3 C4' H4'A 119.4 . . ? C5' C4' H4'A 119.4 . . ? N4 C5' C4' 120(2) . . ? N4 C5' H5'A 120.0 . . ? C4' C5' H5'A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 71.59 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 1.611 _refine_diff_density_min -1.366 _refine_diff_density_rms 0.197