# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Prof Chittaranjan Sinha' _publ_contact_author_address ; Chemistry The University of Burdwan Burdwan-713104 INDIA ; _publ_contact_author_email 'C R SINHA@YAHOO.COM' _publ_section_title ; Copper coordination compounds ; _publ_author_name 'Chittaranjan Sinha' data_a _database_code_depnum_ccdc_archive 'CCDC 244721' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 Cu N11 O S2' _chemical_formula_weight 625.27 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' 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' 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 8.7294(7) _cell_length_b 12.1861(10) _cell_length_c 15.3426(12) _cell_angle_alpha 72.4350(10) _cell_angle_beta 79.6680(10) _cell_angle_gamma 89.855(2) _cell_volume 1528.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 28.27 _exptl_crystal_description irregular _exptl_crystal_colour green _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 650 _exptl_absorpt_coefficient_mu 0.889 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.8185 _exptl_absorpt_correction_T_max 0.9216 _exptl_absorpt_process_details ? _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 '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 15128 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 28.26 _reflns_number_total 6765 _reflns_number_gt 4302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\\s^2^(Fo^2^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6765 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1529 _refine_ls_wR_factor_gt 0.1369 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.892 _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 Cu Cu 0.55492(4) 0.54054(3) 0.75299(3) 0.04846(15) Uani 1 1 d . . . S1 S 1.01436(12) 0.37320(10) 0.83732(8) 0.0820(3) Uani 1 1 d . . . S2 S 0.85493(14) 0.86062(9) 0.53752(9) 0.0890(4) Uani 1 1 d . . . N1 N 0.7458(3) 0.4746(3) 0.7883(2) 0.0651(8) Uani 1 1 d . . . N2 N 0.6736(4) 0.6727(3) 0.6591(2) 0.0729(9) Uani 1 1 d . . . N3 N 0.3591(3) 0.5933(2) 0.70500(17) 0.0464(6) Uani 1 1 d . . . N4 N 0.4288(3) 0.4190(2) 0.86008(18) 0.0464(6) Uani 1 1 d . . . N5 N 0.1687(3) 0.5882(2) 0.62879(18) 0.0507(6) Uani 1 1 d . . . N6 N 0.3625(3) 0.4530(2) 0.62054(18) 0.0482(6) Uani 1 1 d . . . N7 N 0.4887(3) 0.4212(2) 0.64757(18) 0.0488(6) Uani 1 1 d . . . N8 N 0.2557(3) 0.3533(2) 0.99083(18) 0.0516(6) Uani 1 1 d . . . N9 N 0.3345(3) 0.5526(2) 0.94487(18) 0.0505(6) Uani 1 1 d . . . N10 N 0.4320(3) 0.6263(2) 0.88595(18) 0.0478(6) Uani 1 1 d . . . C1 C 0.8577(4) 0.4321(3) 0.8086(2) 0.0515(8) Uani 1 1 d . . . C2 C 0.7468(4) 0.7506(3) 0.6089(2) 0.0532(8) Uani 1 1 d . . . C3 C 0.2576(4) 0.6757(3) 0.7151(3) 0.0601(9) Uani 1 1 d . . . H3 H 0.2674 0.7262 0.7489 0.072 Uiso 1 1 calc R . . C4 C 0.1405(4) 0.6733(3) 0.6687(3) 0.0601(9) Uani 1 1 d . . . H4 H 0.0569 0.7209 0.6648 0.072 Uiso 1 1 calc R . . C5 C 0.0701(4) 0.5494(3) 0.5750(3) 0.0652(10) Uani 1 1 d . . . H5A H -0.0172 0.5972 0.5681 0.098 Uiso 1 1 calc R . . H5B H 0.0333 0.4709 0.6070 0.098 Uiso 1 1 calc R . . H5C H 0.1296 0.5547 0.5147 0.098 Uiso 1 1 calc R . . C6 C 0.3017(3) 0.5416(2) 0.6525(2) 0.0444(7) Uani 1 1 d . . . C7 C 0.5566(4) 0.3299(3) 0.6170(2) 0.0518(8) Uani 1 1 d . . . C8 C 0.5008(4) 0.2851(3) 0.5548(2) 0.0617(9) Uani 1 1 d . . . H8 H 0.4156 0.3160 0.5291 0.074 Uiso 1 1 calc R . . C9 C 0.5725(6) 0.1948(4) 0.5316(3) 0.0814(12) Uani 1 1 d . . . H9 H 0.5359 0.1643 0.4899 0.098 Uiso 1 1 calc R . . C10 C 0.6987(6) 0.1490(4) 0.5698(3) 0.0890(14) Uani 1 1 d . . . H10 H 0.7462 0.0875 0.5540 0.107 Uiso 1 1 calc R . . C11 C 0.7546(5) 0.1933(4) 0.6307(3) 0.0851(13) Uani 1 1 d . . . H11 H 0.8402 0.1621 0.6558 0.102 Uiso 1 1 calc R . . C12 C 0.6834(4) 0.2851(3) 0.6551(3) 0.0665(10) Uani 1 1 d . . . H12 H 0.7208 0.3156 0.6965 0.080 Uiso 1 1 calc R . . C13 C 0.3970(4) 0.3039(3) 0.8779(2) 0.0549(8) Uani 1 1 d . . . H13 H 0.4415 0.2602 0.8406 0.066 Uiso 1 1 calc R . . C14 C 0.2906(4) 0.2624(3) 0.9582(2) 0.0576(9) Uani 1 1 d . . . H14 H 0.2498 0.1868 0.9854 0.069 Uiso 1 1 calc R . . C15 C 0.1393(5) 0.3519(3) 1.0727(3) 0.0754(11) Uani 1 1 d . . . H15A H 0.0957 0.2747 1.1034 0.113 Uiso 1 1 calc R . . H15B H 0.0580 0.4016 1.0537 0.113 Uiso 1 1 calc R . . H15C H 0.1878 0.3783 1.1146 0.113 Uiso 1 1 calc R . . C16 C 0.3419(4) 0.4460(2) 0.9299(2) 0.0465(7) Uani 1 1 d . . . C17 C 0.4273(4) 0.7391(3) 0.8955(2) 0.0505(8) Uani 1 1 d . . . C18 C 0.5350(5) 0.8191(3) 0.8324(3) 0.0665(10) Uani 1 1 d . . . H18 H 0.6039 0.7985 0.7869 0.080 Uiso 1 1 calc R . . C19 C 0.5406(6) 0.9310(3) 0.8369(3) 0.0874(13) Uani 1 1 d . . . H19 H 0.6135 0.9859 0.7947 0.105 Uiso 1 1 calc R . . C20 C 0.4386(7) 0.9599(3) 0.9034(4) 0.0916(15) Uani 1 1 d . . . H20 H 0.4432 1.0346 0.9069 0.110 Uiso 1 1 calc R . . C21 C 0.3301(6) 0.8814(4) 0.9648(3) 0.0868(13) Uani 1 1 d . . . H21 H 0.2601 0.9032 1.0091 0.104 Uiso 1 1 calc R . . C22 C 0.3231(5) 0.7693(3) 0.9620(3) 0.0657(10) Uani 1 1 d . . . H22 H 0.2492 0.7152 1.0043 0.079 Uiso 1 1 calc R . . C23 C 0.9978(6) 0.9652(4) 0.1433(4) 0.0981(15) Uani 1 1 d . . . H23 H 0.9452 0.9171 0.1073 0.21(3) Uiso 1 1 d . . . C24 C 0.8016(7) 0.8598(5) 0.2727(4) 0.1182(19) Uani 1 1 d . . . H24A H 0.7491 0.8692 0.3304 0.177 Uiso 1 1 calc R . . H24B H 0.8569 0.7903 0.2852 0.177 Uiso 1 1 calc R . . H24C H 0.7263 0.8553 0.2352 0.177 Uiso 1 1 calc R . . C25 C 0.9160(3) 1.0481(2) 0.26221(19) 0.151(3) Uani 1 1 d . . . H25A H 0.8464 1.0288 0.3213 0.227 Uiso 1 1 calc R . . H25B H 0.8850 1.1173 0.2211 0.227 Uiso 1 1 calc R . . H25C H 1.0204 1.0601 0.2706 0.227 Uiso 1 1 calc R . . N11 N 0.9106(3) 0.9574(2) 0.22363(19) 0.0827(10) Uani 1 1 d R . . O O 1.0890(3) 1.0446(2) 0.09649(19) 0.1329(14) Uani 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 Cu 0.0393(2) 0.0505(2) 0.0520(3) -0.00822(17) -0.01214(17) 0.00254(16) S1 0.0487(6) 0.0911(7) 0.0910(8) -0.0028(6) -0.0179(5) 0.0172(5) S2 0.0739(7) 0.0653(6) 0.1013(9) 0.0053(6) -0.0018(6) -0.0054(5) N1 0.0478(17) 0.076(2) 0.0666(19) -0.0117(15) -0.0150(15) 0.0075(15) N2 0.0536(18) 0.073(2) 0.076(2) 0.0009(17) -0.0097(16) -0.0035(16) N3 0.0472(15) 0.0448(13) 0.0489(15) -0.0136(11) -0.0151(12) 0.0075(11) N4 0.0440(15) 0.0452(14) 0.0515(15) -0.0136(12) -0.0150(12) 0.0033(11) N5 0.0462(15) 0.0609(16) 0.0468(15) -0.0152(12) -0.0151(12) 0.0050(12) N6 0.0453(15) 0.0510(14) 0.0472(14) -0.0141(11) -0.0075(12) 0.0005(11) N7 0.0464(15) 0.0498(14) 0.0473(14) -0.0127(11) -0.0052(12) 0.0022(12) N8 0.0570(17) 0.0488(15) 0.0459(15) -0.0096(12) -0.0102(13) -0.0047(12) N9 0.0554(16) 0.0485(14) 0.0459(15) -0.0118(12) -0.0098(13) -0.0036(12) N10 0.0473(15) 0.0485(14) 0.0477(14) -0.0125(12) -0.0134(12) -0.0027(12) C1 0.0437(18) 0.0543(18) 0.0504(19) -0.0073(14) -0.0084(15) 0.0002(14) C2 0.0440(18) 0.057(2) 0.057(2) -0.0134(16) -0.0107(16) 0.0082(15) C3 0.064(2) 0.058(2) 0.071(2) -0.0279(17) -0.0314(19) 0.0192(17) C4 0.062(2) 0.061(2) 0.065(2) -0.0237(17) -0.0232(18) 0.0200(17) C5 0.055(2) 0.087(3) 0.063(2) -0.0294(19) -0.0244(18) 0.0049(19) C6 0.0422(16) 0.0473(16) 0.0421(16) -0.0105(13) -0.0094(13) 0.0024(13) C7 0.0485(19) 0.0515(18) 0.0483(18) -0.0122(14) 0.0036(15) 0.0045(14) C8 0.066(2) 0.059(2) 0.057(2) -0.0211(17) 0.0010(18) 0.0022(17) C9 0.089(3) 0.079(3) 0.078(3) -0.036(2) 0.002(2) 0.009(2) C10 0.103(4) 0.067(3) 0.090(3) -0.032(2) 0.014(3) 0.015(2) C11 0.074(3) 0.081(3) 0.090(3) -0.018(2) -0.004(2) 0.030(2) C12 0.062(2) 0.066(2) 0.069(2) -0.0199(18) -0.0070(19) 0.0112(18) C13 0.059(2) 0.0449(17) 0.061(2) -0.0130(15) -0.0164(17) 0.0051(15) C14 0.063(2) 0.0455(18) 0.061(2) -0.0080(15) -0.0179(18) -0.0021(15) C15 0.085(3) 0.069(2) 0.061(2) -0.0148(19) 0.006(2) -0.015(2) C16 0.0483(18) 0.0449(16) 0.0453(17) -0.0086(13) -0.0155(14) -0.0024(13) C17 0.059(2) 0.0470(17) 0.0497(18) -0.0145(14) -0.0201(16) 0.0012(14) C18 0.078(3) 0.056(2) 0.061(2) -0.0151(17) -0.0062(19) -0.0092(18) C19 0.111(4) 0.054(2) 0.090(3) -0.013(2) -0.015(3) -0.019(2) C20 0.137(5) 0.047(2) 0.098(4) -0.025(2) -0.037(3) 0.001(3) C21 0.108(4) 0.075(3) 0.085(3) -0.040(2) -0.012(3) 0.014(3) C22 0.076(3) 0.061(2) 0.063(2) -0.0238(18) -0.009(2) 0.0041(18) C23 0.094(4) 0.094(3) 0.092(3) -0.023(3) 0.011(3) -0.028(3) C24 0.108(4) 0.108(4) 0.113(4) -0.018(3) 0.017(3) -0.030(3) C25 0.230(9) 0.089(4) 0.127(5) -0.045(4) 0.007(5) 0.007(5) N11 0.085(3) 0.067(2) 0.087(3) -0.0168(18) -0.002(2) -0.0076(18) O 0.128(3) 0.106(3) 0.132(3) -0.017(2) 0.028(3) -0.038(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 Cu N1 1.942(3) . ? Cu N2 1.953(3) . ? Cu N4 1.999(3) . ? Cu N3 2.009(2) . ? Cu N7 2.612(3) . ? Cu N10 2.627(3) . ? S1 C1 1.613(3) . ? S2 C2 1.624(4) . ? N1 C1 1.152(4) . ? N2 C2 1.135(4) . ? N3 C6 1.323(4) . ? N3 C3 1.363(4) . ? N4 C16 1.324(4) . ? N4 C13 1.365(4) . ? N5 C6 1.352(4) . ? N5 C4 1.356(4) . ? N5 C5 1.461(4) . ? N6 N7 1.265(3) . ? N6 C6 1.381(4) . ? N7 C7 1.421(4) . ? N8 C16 1.353(4) . ? N8 C14 1.360(4) . ? N8 C15 1.462(5) . ? N9 N10 1.259(3) . ? N9 C16 1.386(4) . ? N10 C17 1.425(4) . ? C3 C4 1.351(5) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C7 C12 1.379(5) . ? C7 C8 1.389(5) . ? C8 C9 1.372(5) . ? C8 H8 0.9300 . ? C9 C10 1.378(6) . ? C9 H9 0.9300 . ? C10 C11 1.368(7) . ? C10 H10 0.9300 . ? C11 C12 1.395(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.362(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C17 C18 1.372(5) . ? C17 C22 1.378(5) . ? C18 C19 1.387(5) . ? C18 H18 0.9300 . ? C19 C20 1.359(7) . ? C19 H19 0.9300 . ? C20 C21 1.356(6) . ? C20 H20 0.9300 . ? C21 C22 1.381(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 O 1.210(5) . ? C23 N11 1.305(5) . ? C23 H23 1.070(5) . ? C24 N11 1.448(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N11 1.4066 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 N1 Cu N2 90.91(13) . . ? N1 Cu N4 90.21(11) . . ? N2 Cu N4 172.29(13) . . ? N1 Cu N3 171.62(12) . . ? N2 Cu N3 90.20(11) . . ? N4 Cu N3 89.81(10) . . ? N1 Cu N7 102.06(11) . . ? N2 Cu N7 100.41(12) . . ? N4 Cu N7 86.81(9) . . ? N3 Cu N7 69.58(9) . . ? N1 Cu N10 105.18(11) . . ? N2 Cu N10 103.25(12) . . ? N4 Cu N10 69.11(9) . . ? N3 Cu N10 82.63(9) . . ? N7 Cu N10 143.31(8) . . ? C1 N1 Cu 177.7(3) . . ? C2 N2 Cu 175.7(3) . . ? C6 N3 C3 105.2(3) . . ? C6 N3 Cu 120.4(2) . . ? C3 N3 Cu 134.4(2) . . ? C16 N4 C13 105.2(3) . . ? C16 N4 Cu 120.9(2) . . ? C13 N4 Cu 133.7(2) . . ? C6 N5 C4 106.8(3) . . ? C6 N5 C5 126.3(3) . . ? C4 N5 C5 126.9(3) . . ? N7 N6 C6 112.3(3) . . ? N6 N7 C7 114.8(3) . . ? N6 N7 Cu 109.47(18) . . ? C7 N7 Cu 135.7(2) . . ? C16 N8 C14 106.8(3) . . ? C16 N8 C15 126.9(3) . . ? C14 N8 C15 126.1(3) . . ? N10 N9 C16 112.2(3) . . ? N9 N10 C17 115.2(3) . . ? N9 N10 Cu 108.81(18) . . ? C17 N10 Cu 134.5(2) . . ? N1 C1 S1 179.7(4) . . ? N2 C2 S2 178.8(3) . . ? N3 C3 C4 110.0(3) . . ? N3 C3 H3 125.0 . . ? C4 C3 H3 125.0 . . ? N5 C4 C3 106.7(3) . . ? N5 C4 H4 126.6 . . ? C3 C4 H4 126.6 . . ? N5 C5 H5A 109.5 . . ? N5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 N5 111.3(3) . . ? N3 C6 N6 128.3(3) . . ? N5 C6 N6 120.5(3) . . ? C12 C7 C8 120.7(3) . . ? C12 C7 N7 115.2(3) . . ? C8 C7 N7 124.0(3) . . ? C9 C8 C7 119.4(4) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 120.2(4) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 120.6(4) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.0(4) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C7 C12 C11 119.0(4) . . ? C7 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C14 C13 N4 110.1(3) . . ? C14 C13 H13 125.0 . . ? N4 C13 H13 125.0 . . ? N8 C14 C13 106.3(3) . . ? N8 C14 H14 126.8 . . ? C13 C14 H14 126.8 . . ? N8 C15 H15A 109.5 . . ? N8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N4 C16 N8 111.6(3) . . ? N4 C16 N9 127.6(3) . . ? N8 C16 N9 120.8(3) . . ? C18 C17 C22 120.7(3) . . ? C18 C17 N10 115.3(3) . . ? C22 C17 N10 124.0(3) . . ? C17 C18 C19 119.5(4) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C20 C19 C18 119.5(4) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C19 C20 C21 121.1(4) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C20 C21 C22 120.4(4) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C17 C22 C21 118.8(4) . . ? C17 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? O C23 N11 126.1(5) . . ? O C23 H23 117.2(5) . . ? N11 C23 H23 111.1(4) . . ? N11 C24 H24A 109.5 . . ? N11 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N11 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N11 C25 H25A 109.5 . . ? N11 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N11 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 N11 C25 119.8(2) . . ? C23 N11 C24 121.7(4) . . ? C25 N11 C24 118.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu N1 C1 -123(8) . . . . ? N4 Cu N1 C1 64(8) . . . . ? N3 Cu N1 C1 -26(8) . . . . ? N7 Cu N1 C1 -22(8) . . . . ? N10 Cu N1 C1 133(8) . . . . ? N1 Cu N2 C2 -55(4) . . . . ? N4 Cu N2 C2 43(5) . . . . ? N3 Cu N2 C2 133(4) . . . . ? N7 Cu N2 C2 -157(4) . . . . ? N10 Cu N2 C2 51(4) . . . . ? N1 Cu N3 C6 5.6(9) . . . . ? N2 Cu N3 C6 103.2(2) . . . . ? N4 Cu N3 C6 -84.5(2) . . . . ? N7 Cu N3 C6 2.2(2) . . . . ? N10 Cu N3 C6 -153.5(2) . . . . ? N1 Cu N3 C3 -176.2(7) . . . . ? N2 Cu N3 C3 -78.5(3) . . . . ? N4 Cu N3 C3 93.7(3) . . . . ? N7 Cu N3 C3 -179.6(3) . . . . ? N10 Cu N3 C3 24.8(3) . . . . ? N1 Cu N4 C16 114.1(2) . . . . ? N2 Cu N4 C16 15.8(9) . . . . ? N3 Cu N4 C16 -74.3(2) . . . . ? N7 Cu N4 C16 -143.8(2) . . . . ? N10 Cu N4 C16 7.9(2) . . . . ? N1 Cu N4 C13 -72.6(3) . . . . ? N2 Cu N4 C13 -171.0(8) . . . . ? N3 Cu N4 C13 99.0(3) . . . . ? N7 Cu N4 C13 29.4(3) . . . . ? N10 Cu N4 C13 -178.8(3) . . . . ? C6 N6 N7 C7 179.8(2) . . . . ? C6 N6 N7 Cu 1.6(3) . . . . ? N1 Cu N7 N6 178.4(2) . . . . ? N2 Cu N7 N6 -88.4(2) . . . . ? N4 Cu N7 N6 88.9(2) . . . . ? N3 Cu N7 N6 -2.12(19) . . . . ? N10 Cu N7 N6 41.1(3) . . . . ? N1 Cu N7 C7 0.6(3) . . . . ? N2 Cu N7 C7 93.8(3) . . . . ? N4 Cu N7 C7 -88.9(3) . . . . ? N3 Cu N7 C7 -179.9(3) . . . . ? N10 Cu N7 C7 -136.6(3) . . . . ? C16 N9 N10 C17 178.1(2) . . . . ? C16 N9 N10 Cu 10.1(3) . . . . ? N1 Cu N10 N9 -94.6(2) . . . . ? N2 Cu N10 N9 170.7(2) . . . . ? N4 Cu N10 N9 -10.36(18) . . . . ? N3 Cu N10 N9 82.3(2) . . . . ? N7 Cu N10 N9 41.9(2) . . . . ? N1 Cu N10 C17 100.6(3) . . . . ? N2 Cu N10 C17 6.0(3) . . . . ? N4 Cu N10 C17 -175.1(3) . . . . ? N3 Cu N10 C17 -82.5(3) . . . . ? N7 Cu N10 C17 -122.8(3) . . . . ? Cu N1 C1 S1 -160(100) . . . . ? Cu N2 C2 S2 60(20) . . . . ? C6 N3 C3 C4 -0.1(4) . . . . ? Cu N3 C3 C4 -178.6(2) . . . . ? C6 N5 C4 C3 0.1(4) . . . . ? C5 N5 C4 C3 176.9(3) . . . . ? N3 C3 C4 N5 0.0(4) . . . . ? C3 N3 C6 N5 0.2(4) . . . . ? Cu N3 C6 N5 178.90(19) . . . . ? C3 N3 C6 N6 178.8(3) . . . . ? Cu N3 C6 N6 -2.5(4) . . . . ? C4 N5 C6 N3 -0.2(4) . . . . ? C5 N5 C6 N3 -177.0(3) . . . . ? C4 N5 C6 N6 -178.9(3) . . . . ? C5 N5 C6 N6 4.3(5) . . . . ? N7 N6 C6 N3 0.2(4) . . . . ? N7 N6 C6 N5 178.6(3) . . . . ? N6 N7 C7 C12 -172.4(3) . . . . ? Cu N7 C7 C12 5.2(4) . . . . ? N6 N7 C7 C8 6.3(4) . . . . ? Cu N7 C7 C8 -176.0(2) . . . . ? C12 C7 C8 C9 0.3(5) . . . . ? N7 C7 C8 C9 -178.3(3) . . . . ? C7 C8 C9 C10 0.1(6) . . . . ? C8 C9 C10 C11 -0.4(7) . . . . ? C9 C10 C11 C12 0.4(7) . . . . ? C8 C7 C12 C11 -0.4(5) . . . . ? N7 C7 C12 C11 178.4(3) . . . . ? C10 C11 C12 C7 0.0(6) . . . . ? C16 N4 C13 C14 0.2(4) . . . . ? Cu N4 C13 C14 -173.8(2) . . . . ? C16 N8 C14 C13 -0.3(3) . . . . ? C15 N8 C14 C13 176.0(3) . . . . ? N4 C13 C14 N8 0.0(4) . . . . ? C13 N4 C16 N8 -0.4(3) . . . . ? Cu N4 C16 N8 174.58(19) . . . . ? C13 N4 C16 N9 178.7(3) . . . . ? Cu N4 C16 N9 -6.3(4) . . . . ? C14 N8 C16 N4 0.4(3) . . . . ? C15 N8 C16 N4 -175.8(3) . . . . ? C14 N8 C16 N9 -178.8(3) . . . . ? C15 N8 C16 N9 5.0(5) . . . . ? N10 N9 C16 N4 -4.9(4) . . . . ? N10 N9 C16 N8 174.2(3) . . . . ? N9 N10 C17 C18 179.0(3) . . . . ? Cu N10 C17 C18 -17.0(4) . . . . ? N9 N10 C17 C22 -1.5(4) . . . . ? Cu N10 C17 C22 162.5(3) . . . . ? C22 C17 C18 C19 1.2(6) . . . . ? N10 C17 C18 C19 -179.3(4) . . . . ? C17 C18 C19 C20 -0.4(7) . . . . ? C18 C19 C20 C21 -0.8(8) . . . . ? C19 C20 C21 C22 1.2(8) . . . . ? C18 C17 C22 C21 -0.8(6) . . . . ? N10 C17 C22 C21 179.7(3) . . . . ? C20 C21 C22 C17 -0.4(7) . . . . ? O C23 N11 C25 1.3(8) . . . . ? O C23 N11 C24 178.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.892 _refine_diff_density_max 0.418 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.052 data_b _database_code_depnum_ccdc_archive 'CCDC 244722' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 Cu N14' _chemical_formula_weight 576.14 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8632(8) _cell_length_b 17.6782(13) _cell_length_c 26.703(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5600.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description brick _exptl_crystal_colour brown _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2392 _exptl_absorpt_coefficient_mu 0.821 _exptl_absorpt_correction_type ? _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 'Bruker 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 31899 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.32 _reflns_number_total 6480 _reflns_number_gt 3521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\\s^2^(Fo^2^)+(0.0613P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6480 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1149 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 Cu Cu 0.24027(3) 0.030542(19) 0.137057(12) 0.05354(13) Uani 1 1 d . . . N1 N 0.34440(19) -0.05493(12) 0.11886(9) 0.0517(6) Uani 1 1 d . . . N2 N 0.49269(19) -0.10895(13) 0.08369(9) 0.0553(6) Uani 1 1 d . . . N3 N 0.48376(19) 0.02526(13) 0.07782(8) 0.0516(6) Uani 1 1 d . . . N4 N 0.41932(19) 0.08037(13) 0.08688(8) 0.0508(5) Uani 1 1 d . . . N5 N 0.3239(2) 0.04783(13) 0.20157(9) 0.0588(6) Uani 1 1 d . . . N6 N 0.3615(2) 0.03662(13) 0.28259(9) 0.0562(6) Uani 1 1 d . . . N7 N 0.2132(2) -0.04110(12) 0.25153(9) 0.0543(6) Uani 1 1 d . . . N8 N 0.16231(19) -0.05804(13) 0.21142(9) 0.0554(6) Uani 1 1 d . . . N9 N 0.1419(2) 0.00304(15) 0.08095(10) 0.0663(7) Uani 1 1 d . . . N10 N 0.1873(2) -0.01368(14) 0.04229(11) 0.0655(7) Uani 1 1 d . . . N11 N 0.2278(3) -0.03047(18) 0.00448(12) 0.0930(10) Uani 1 1 d . . . N12 N 0.1588(2) 0.12561(17) 0.15058(11) 0.0792(9) Uani 1 1 d . . . N13 N 0.0744(3) 0.14309(14) 0.13201(11) 0.0720(8) Uani 1 1 d . . . C1 C 0.3351(3) -0.13141(16) 0.12302(11) 0.0611(8) Uani 1 1 d . . . H1 H 0.2757 -0.1569 0.1383 0.073 Uiso 1 1 calc R . . C2 C 0.4256(3) -0.16444(17) 0.10153(12) 0.0629(8) Uani 1 1 d . . . H2 H 0.4393 -0.2161 0.0994 0.076 Uiso 1 1 calc R . . C3 C 0.4401(2) -0.04295(15) 0.09447(10) 0.0493(7) Uani 1 1 d . . . C4 C 0.4587(2) 0.15071(15) 0.06851(10) 0.0497(7) Uani 1 1 d . . . C5 C 0.5637(2) 0.16223(17) 0.04761(11) 0.0583(7) Uani 1 1 d . . . H5 H 0.6157 0.1229 0.0461 0.070 Uiso 1 1 calc R . . C6 C 0.5907(3) 0.23242(17) 0.02914(11) 0.0634(8) Uani 1 1 d . . . H6 H 0.6619 0.2402 0.0156 0.076 Uiso 1 1 calc R . . C7 C 0.5148(3) 0.29188(16) 0.03012(11) 0.0622(8) Uani 1 1 d . . . C8 C 0.4106(3) 0.27924(16) 0.05075(11) 0.0627(8) Uani 1 1 d . . . H8 H 0.3582 0.3184 0.0516 0.075 Uiso 1 1 calc R . . C9 C 0.3821(2) 0.20966(15) 0.07027(10) 0.0564(7) Uani 1 1 d . . . H9 H 0.3115 0.2023 0.0846 0.068 Uiso 1 1 calc R . . C10 C 0.6037(3) -0.11857(18) 0.06053(12) 0.0677(9) Uani 1 1 d . . . H10A H 0.6306 -0.0700 0.0485 0.081 Uiso 1 1 calc R . . H10B H 0.5973 -0.1523 0.0320 0.081 Uiso 1 1 calc R . . C11 C 0.6865(3) -0.1505(2) 0.09719(14) 0.0920(11) Uani 1 1 d . . . H11A H 0.7585 -0.1563 0.0812 0.138 Uiso 1 1 calc R . . H11B H 0.6605 -0.1989 0.1087 0.138 Uiso 1 1 calc R . . H11C H 0.6937 -0.1168 0.1252 0.138 Uiso 1 1 calc R . . C12 C 0.5455(3) 0.36892(18) 0.00919(15) 0.0907(11) Uani 1 1 d . . . H12A H 0.6210 0.3675 -0.0037 0.136 Uiso 1 1 calc R . . H12B H 0.5407 0.4061 0.0353 0.136 Uiso 1 1 calc R . . H12C H 0.4942 0.3819 -0.0173 0.136 Uiso 1 1 calc R . . C13 C 0.4091(3) 0.09503(19) 0.21395(12) 0.0717(9) Uani 1 1 d . . . H13 H 0.4457 0.1274 0.1918 0.086 Uiso 1 1 calc R . . C14 C 0.4338(3) 0.08840(18) 0.26350(12) 0.0702(9) Uani 1 1 d . . . H14 H 0.4896 0.1144 0.2809 0.084 Uiso 1 1 calc R . . C15 C 0.2960(2) 0.01306(16) 0.24379(10) 0.0522(7) Uani 1 1 d . . . C16 C 0.0771(2) -0.11359(16) 0.21654(11) 0.0537(7) Uani 1 1 d . . . C17 C 0.0314(2) -0.14112(17) 0.17288(11) 0.0606(8) Uani 1 1 d . . . H17 H 0.0568 -0.1228 0.1422 0.073 Uiso 1 1 calc R . . C18 C -0.0510(3) -0.19532(18) 0.17407(13) 0.0658(8) Uani 1 1 d . . . H18 H -0.0792 -0.2143 0.1441 0.079 Uiso 1 1 calc R . . C19 C -0.0932(3) -0.22233(17) 0.21859(13) 0.0651(8) Uani 1 1 d . . . C20 C -0.0468(3) -0.1946(2) 0.26187(13) 0.0827(10) Uani 1 1 d . . . H20 H -0.0730 -0.2128 0.2924 0.099 Uiso 1 1 calc R . . C21 C 0.0363(3) -0.1413(2) 0.26169(12) 0.0774(10) Uani 1 1 d . . . H21 H 0.0656 -0.1235 0.2918 0.093 Uiso 1 1 calc R . . C22 C 0.3533(3) 0.01107(17) 0.33486(11) 0.0647(8) Uani 1 1 d . . . H22A H 0.4253 0.0188 0.3513 0.078 Uiso 1 1 calc R . . H22B H 0.3371 -0.0427 0.3354 0.078 Uiso 1 1 calc R . . C23 C 0.2639(3) 0.0520(2) 0.36336(13) 0.0920(12) Uani 1 1 d . . . H23A H 0.2617 0.0334 0.3971 0.138 Uiso 1 1 calc R . . H23B H 0.1921 0.0436 0.3477 0.138 Uiso 1 1 calc R . . H23C H 0.2803 0.1051 0.3636 0.138 Uiso 1 1 calc R . . C24 C -0.1870(3) -0.2801(2) 0.21981(16) 0.0987(12) Uani 1 1 d . . . H24A H -0.2048 -0.2922 0.2540 0.148 Uiso 1 1 calc R . . H24B H -0.1633 -0.3251 0.2026 0.148 Uiso 1 1 calc R . . H24C H -0.2526 -0.2597 0.2036 0.148 Uiso 1 1 calc R . . N14 N -0.0125(3) 0.16336(17) 0.11504(16) 0.1062(12) 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 Cu 0.0587(2) 0.0568(2) 0.0451(2) -0.00033(16) 0.00327(16) 0.00188(17) N1 0.0530(15) 0.0519(13) 0.0501(14) 0.0074(11) -0.0018(11) 0.0022(11) N2 0.0584(15) 0.0544(14) 0.0530(14) 0.0039(11) 0.0005(12) 0.0069(12) N3 0.0541(14) 0.0525(14) 0.0481(14) 0.0015(11) -0.0003(11) -0.0020(12) N4 0.0566(14) 0.0521(13) 0.0438(13) 0.0007(11) 0.0022(11) 0.0009(12) N5 0.0611(16) 0.0678(16) 0.0475(15) -0.0003(12) 0.0028(11) -0.0122(13) N6 0.0622(15) 0.0592(14) 0.0472(14) -0.0007(12) -0.0002(11) -0.0072(12) N7 0.0583(15) 0.0574(14) 0.0471(14) -0.0014(11) 0.0010(11) -0.0044(11) N8 0.0573(15) 0.0617(14) 0.0470(15) -0.0009(11) 0.0018(11) -0.0019(12) N9 0.0693(18) 0.0779(18) 0.0517(17) -0.0062(14) -0.0056(13) 0.0145(14) N10 0.0759(19) 0.0612(16) 0.0593(19) 0.0043(14) -0.0106(16) 0.0092(14) N11 0.112(3) 0.111(3) 0.0560(19) -0.0073(18) 0.0063(17) 0.0130(19) N12 0.068(2) 0.087(2) 0.083(2) -0.0158(16) -0.0038(16) 0.0250(16) N13 0.095(2) 0.0463(16) 0.075(2) 0.0013(14) 0.0275(19) -0.0033(16) C1 0.066(2) 0.0561(18) 0.061(2) 0.0132(15) 0.0029(15) -0.0006(15) C2 0.076(2) 0.0480(16) 0.065(2) 0.0051(15) -0.0063(17) 0.0083(16) C3 0.0512(17) 0.0538(17) 0.0428(15) 0.0022(13) -0.0033(12) 0.0053(14) C4 0.0545(17) 0.0547(17) 0.0399(15) 0.0015(12) 0.0006(12) -0.0029(14) C5 0.0603(19) 0.0606(18) 0.0539(18) 0.0025(14) 0.0011(14) -0.0015(15) C6 0.059(2) 0.074(2) 0.058(2) 0.0029(16) 0.0062(15) -0.0121(17) C7 0.079(2) 0.0579(19) 0.0497(18) 0.0067(14) -0.0046(16) -0.0150(17) C8 0.075(2) 0.0546(18) 0.0586(19) 0.0012(15) 0.0013(16) 0.0031(16) C9 0.0585(19) 0.0586(18) 0.0520(18) 0.0008(14) 0.0075(14) -0.0055(15) C10 0.070(2) 0.075(2) 0.057(2) -0.0076(16) 0.0100(16) 0.0129(17) C11 0.070(2) 0.111(3) 0.095(3) -0.006(2) 0.000(2) 0.016(2) C12 0.107(3) 0.074(2) 0.090(3) 0.025(2) 0.004(2) -0.014(2) C13 0.080(2) 0.079(2) 0.056(2) 0.0009(17) 0.0051(17) -0.0256(19) C14 0.074(2) 0.079(2) 0.058(2) -0.0036(17) -0.0043(17) -0.0227(18) C15 0.0563(17) 0.0578(17) 0.0424(16) -0.0025(13) -0.0008(13) -0.0007(14) C16 0.0537(18) 0.0566(17) 0.0506(18) -0.0042(14) 0.0030(14) -0.0019(14) C17 0.0595(19) 0.075(2) 0.0470(18) -0.0018(15) 0.0007(14) 0.0003(16) C18 0.062(2) 0.078(2) 0.058(2) -0.0087(16) -0.0086(16) -0.0044(17) C19 0.060(2) 0.0641(19) 0.072(2) -0.0087(17) 0.0047(16) -0.0031(15) C20 0.098(3) 0.093(3) 0.057(2) -0.0050(18) 0.0150(19) -0.031(2) C21 0.094(3) 0.091(2) 0.0468(19) -0.0071(17) 0.0049(16) -0.030(2) C22 0.080(2) 0.0665(19) 0.0481(19) 0.0041(15) -0.0093(15) -0.0026(16) C23 0.119(3) 0.096(3) 0.062(2) 0.0057(19) 0.019(2) 0.009(2) C24 0.087(3) 0.094(3) 0.114(3) -0.003(2) 0.002(3) -0.031(2) N14 0.109(3) 0.0652(19) 0.144(3) 0.012(2) -0.004(2) 0.009(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 Cu N9 1.960(3) . ? Cu N12 1.972(3) . ? Cu N4 2.661(2) . ? Cu N5 2.011(2) . ? Cu N1 2.011(2) . ? Cu N8 2.693(2) . ? N1 C3 1.326(3) . ? N1 C1 1.361(3) . ? N2 C2 1.350(4) . ? N2 C3 1.354(3) . ? N2 C10 1.464(4) . ? N3 N4 1.262(3) . ? N3 C3 1.386(3) . ? N4 C4 1.416(3) . ? N5 C15 1.326(3) . ? N5 C13 1.352(4) . ? N6 C14 1.354(4) . ? N6 C15 1.360(3) . ? N6 C22 1.470(4) . ? N7 N8 1.266(3) . ? N7 C15 1.387(4) . ? N8 C16 1.415(3) . ? N9 N10 1.201(4) . ? N10 N11 1.156(4) . ? N12 N13 1.159(4) . ? N13 N14 1.182(4) . ? C1 C2 1.351(4) . ? C4 C5 1.381(4) . ? C4 C9 1.383(4) . ? C5 C6 1.373(4) . ? C6 C7 1.384(4) . ? C7 C8 1.372(4) . ? C7 C12 1.517(4) . ? C8 C9 1.378(4) . ? C10 C11 1.498(4) . ? C13 C14 1.360(4) . ? C16 C17 1.375(4) . ? C16 C21 1.389(4) . ? C17 C18 1.370(4) . ? C18 C19 1.375(4) . ? C19 C20 1.370(4) . ? C19 C24 1.511(4) . ? C20 C21 1.364(4) . ? C22 C23 1.492(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N4 68.70(8) . . ? N4 Cu N9 99.93(9) . . ? N9 Cu N12 93.42(11) . . ? N9 Cu N5 170.38(11) . . ? N12 Cu N5 87.44(11) . . ? N9 Cu N1 89.69(10) . . ? N12 Cu N1 170.23(11) . . ? N5 Cu N1 91.04(9) . . ? N8 Cu N9 102.41(9) . . ? N8 Cu N12 101.08(10) . . ? C3 N1 C1 105.6(2) . . ? C3 N1 Cu 121.64(18) . . ? C1 N1 Cu 132.6(2) . . ? C2 N2 C3 106.2(2) . . ? C2 N2 C10 126.5(2) . . ? C3 N2 C10 127.2(2) . . ? N4 N3 C3 112.6(2) . . ? N3 N4 C4 114.3(2) . . ? C15 N5 C13 105.3(2) . . ? C15 N5 Cu 122.34(19) . . ? C13 N5 Cu 132.2(2) . . ? C14 N6 C15 106.4(2) . . ? C14 N6 C22 127.4(3) . . ? C15 N6 C22 126.3(2) . . ? N8 N7 C15 112.0(2) . . ? N7 N8 C16 115.0(2) . . ? N10 N9 Cu 116.8(2) . . ? N11 N10 N9 177.9(4) . . ? N13 N12 Cu 124.9(3) . . ? N12 N13 N14 176.7(4) . . ? C2 C1 N1 109.3(3) . . ? N2 C2 C1 107.7(3) . . ? N1 C3 N2 111.2(2) . . ? N1 C3 N3 128.1(2) . . ? N2 C3 N3 120.6(2) . . ? C5 C4 C9 119.7(3) . . ? C5 C4 N4 124.5(3) . . ? C9 C4 N4 115.7(2) . . ? C6 C5 C4 119.2(3) . . ? C5 C6 C7 121.9(3) . . ? C8 C7 C6 118.0(3) . . ? C8 C7 C12 120.7(3) . . ? C6 C7 C12 121.3(3) . . ? C7 C8 C9 121.2(3) . . ? C8 C9 C4 119.9(3) . . ? N2 C10 C11 111.0(3) . . ? N5 C13 C14 110.2(3) . . ? N6 C14 C13 106.7(3) . . ? N5 C15 N6 111.3(3) . . ? N5 C15 N7 128.5(3) . . ? N6 C15 N7 120.1(3) . . ? C17 C16 C21 118.3(3) . . ? C17 C16 N8 116.4(3) . . ? C21 C16 N8 125.3(3) . . ? C18 C17 C16 120.6(3) . . ? C17 C18 C19 121.5(3) . . ? C20 C19 C18 117.3(3) . . ? C20 C19 C24 121.3(3) . . ? C18 C19 C24 121.4(3) . . ? C21 C20 C19 122.3(3) . . ? C20 C21 C16 119.9(3) . . ? N6 C22 C23 112.5(3) . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.446 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.049