# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Xiao-Ming Chen' _publ_contact_author_address ; School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou 510275 CHINA ; _publ_contact_author_email CESCXM@ZSU.EDU.CN _publ_section_title ; Molecular Chairs, Zippers, Zigzag and Helical Chains: Chemical Enumeration of Supramolecular Isomerism Based on a Predesigned Metal-Organic Building Block ; loop_ _publ_author_name _publ_author_address 'Jie-Peng Zhang' ; School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou 510275 P. R. China ; 'Yan-Yong Lin' ; School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou 510275 P. R. China ; 'Xiao-Chun Huang' ; School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou 510275 P. R. China ; 'Xiao-Ming Chen' ; School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou 510275 P. R. China ; #====================================== data_isomer_I _database_code_depnum_ccdc_archive 'CCDC 246255' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cu N5' _chemical_formula_weight 285.77 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)/c 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 13.2428(9) _cell_length_b 19.5571(12) _cell_length_c 9.1855(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.530(9) _cell_angle_gamma 90.00 _cell_volume 2280.6(3) _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 polyhedron _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5558 _exptl_absorpt_correction_T_max 0.8039 _exptl_absorpt_process_details 'Bruker SADABS' _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 Apex CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17968 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5479 _reflns_number_gt 3978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART for Windows NT, Bruker AXS Inc., 1998.' _computing_cell_refinement 'SAINT-PLUS for Windows NT, Ver. 6.0' _computing_data_reduction 'SAINT-PLUS for Windows NT, Ver. 6.0' _computing_structure_solution 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_publication_material 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _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^)+(0.0461P)^2^+0.8586P] 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 5479 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.38352(3) 0.402032(19) 0.15273(4) 0.05079(13) Uani 1 1 d . . . Cu2 Cu 0.22273(3) 0.556025(18) 0.34138(4) 0.05571(14) Uani 1 1 d . . . N1 N 0.23418(16) 0.43013(11) 0.1529(2) 0.0396(5) Uani 1 1 d . . . N2 N 0.18270(16) 0.47493(10) 0.2180(2) 0.0390(5) Uani 1 1 d . . . N3 N 0.06308(16) 0.40086(10) 0.0805(2) 0.0382(5) Uani 1 1 d . . . N4 N 0.29880(16) 0.33049(11) 0.0037(2) 0.0398(5) Uani 1 1 d . . . N5 N 0.04577(18) 0.54395(11) 0.3278(3) 0.0448(5) Uani 1 1 d . . . N6 N 0.54465(17) 0.31879(11) 0.4200(3) 0.0437(5) Uani 1 1 d . . . N7 N 0.50596(16) 0.37403(11) 0.3295(2) 0.0415(5) Uani 1 1 d . . . N8 N 0.65260(16) 0.40876(10) 0.5022(2) 0.0384(5) Uani 1 1 d . . . N9 N 0.77665(17) 0.34090(11) 0.7397(3) 0.0440(5) Uani 1 1 d . . . N10 N 0.46727(17) 0.49454(12) 0.1833(3) 0.0442(5) Uani 1 1 d . . . C1 C 0.16072(18) 0.38767(13) 0.0713(3) 0.0362(6) Uani 1 1 d . . . C2 C 0.08093(19) 0.45567(12) 0.1731(3) 0.0364(6) Uani 1 1 d . . . C3 C 0.19479(19) 0.33115(13) -0.0079(3) 0.0386(6) Uani 1 1 d . . . C4 C 0.1275(2) 0.27992(15) -0.0818(4) 0.0585(8) Uani 1 1 d . . . H4A H 0.0561 0.2817 -0.0888 0.070 Uiso 1 1 calc R . . C5 C 0.1679(3) 0.22626(18) -0.1449(4) 0.0697(10) Uani 1 1 d . . . H5A H 0.1239 0.1915 -0.1957 0.084 Uiso 1 1 calc R . . C6 C 0.2734(3) 0.22461(17) -0.1321(4) 0.0599(8) Uani 1 1 d . . . H6A H 0.3024 0.1885 -0.1723 0.072 Uiso 1 1 calc R . . C7 C 0.3355(2) 0.27750(15) -0.0585(3) 0.0482(7) Uani 1 1 d . . . H7A H 0.4069 0.2765 -0.0515 0.058 Uiso 1 1 calc R . . C8 C 0.0047(2) 0.49298(12) 0.2293(3) 0.0374(6) Uani 1 1 d . . . C9 C -0.1019(2) 0.47816(16) 0.1876(3) 0.0494(7) Uani 1 1 d . . . H9A H -0.1283 0.4429 0.1194 0.059 Uiso 1 1 calc R . . C10 C -0.1685(3) 0.51560(18) 0.2470(4) 0.0641(9) Uani 1 1 d . . . H10A H -0.2402 0.5061 0.2199 0.077 Uiso 1 1 calc R . . C11 C -0.1269(3) 0.56736(18) 0.3474(4) 0.0649(9) Uani 1 1 d . . . H11A H -0.1699 0.5937 0.3897 0.078 Uiso 1 1 calc R . . C12 C -0.0200(3) 0.57937(17) 0.3839(4) 0.0584(8) Uani 1 1 d . . . H12A H 0.0077 0.6144 0.4519 0.070 Uiso 1 1 calc R . . C13 C 0.63124(19) 0.34207(13) 0.5205(3) 0.0388(6) Uani 1 1 d . . . C14 C 0.57150(19) 0.42633(13) 0.3820(3) 0.0369(6) Uani 1 1 d . . . C15 C 0.7001(2) 0.30280(13) 0.6459(3) 0.0406(6) Uani 1 1 d . . . C16 C 0.6897(2) 0.23374(15) 0.6680(3) 0.0520(7) Uani 1 1 d . . . H16A H 0.6360 0.2088 0.6022 0.062 Uiso 1 1 calc R . . C17 C 0.7605(3) 0.20203(16) 0.7898(4) 0.0584(8) Uani 1 1 d . . . H17A H 0.7560 0.1553 0.8058 0.070 Uiso 1 1 calc R . . C18 C 0.8375(3) 0.24075(17) 0.8866(4) 0.0597(8) Uani 1 1 d . . . H18A H 0.8852 0.2208 0.9702 0.072 Uiso 1 1 calc R . . C19 C 0.8432(2) 0.30955(16) 0.8583(4) 0.0538(8) Uani 1 1 d . . . H19A H 0.8955 0.3354 0.9244 0.065 Uiso 1 1 calc R . . C20 C 0.54740(19) 0.49375(13) 0.3137(3) 0.0378(6) Uani 1 1 d . . . C21 C 0.5964(2) 0.55318(14) 0.3802(3) 0.0464(7) Uani 1 1 d . . . H21A H 0.6516 0.5512 0.4692 0.056 Uiso 1 1 calc R . . C22 C 0.5622(3) 0.61536(15) 0.3130(4) 0.0559(8) Uani 1 1 d . . . H22A H 0.5945 0.6558 0.3555 0.067 Uiso 1 1 calc R . . C23 C 0.4798(3) 0.61658(17) 0.1824(4) 0.0601(8) Uani 1 1 d . . . H23A H 0.4545 0.6579 0.1359 0.072 Uiso 1 1 calc R . . C24 C 0.4355(2) 0.55568(16) 0.1215(4) 0.0564(8) Uani 1 1 d . . . H24A H 0.3802 0.5570 0.0324 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.03048(19) 0.0565(2) 0.0587(2) -0.00671(17) 0.00178(15) -0.00875(15) Cu2 0.0509(2) 0.0438(2) 0.0644(2) -0.01515(17) 0.00325(18) -0.01578(16) N1 0.0294(11) 0.0358(11) 0.0492(12) -0.0073(9) 0.0042(9) -0.0001(9) N2 0.0298(11) 0.0341(11) 0.0482(12) -0.0077(10) 0.0030(9) -0.0010(9) N3 0.0309(11) 0.0349(11) 0.0447(12) -0.0047(9) 0.0042(9) -0.0016(8) N4 0.0327(11) 0.0399(12) 0.0442(12) -0.0036(10) 0.0069(9) -0.0006(9) N5 0.0423(13) 0.0382(12) 0.0532(13) -0.0082(10) 0.0122(11) -0.0025(10) N6 0.0325(11) 0.0403(12) 0.0547(13) -0.0046(10) 0.0065(10) -0.0059(9) N7 0.0299(11) 0.0418(12) 0.0495(13) -0.0049(10) 0.0062(9) -0.0055(9) N8 0.0304(11) 0.0354(11) 0.0458(12) -0.0055(9) 0.0049(9) -0.0025(8) N9 0.0315(11) 0.0391(12) 0.0571(14) -0.0053(10) 0.0057(10) -0.0018(9) N10 0.0353(12) 0.0483(13) 0.0475(12) 0.0004(10) 0.0096(10) -0.0029(10) C1 0.0286(12) 0.0356(13) 0.0398(13) -0.0019(10) 0.0021(10) -0.0014(10) C2 0.0290(12) 0.0346(13) 0.0406(13) -0.0003(10) 0.0020(10) -0.0013(10) C3 0.0343(13) 0.0355(13) 0.0426(14) -0.0057(11) 0.0052(11) 0.0018(11) C4 0.0365(15) 0.0553(18) 0.081(2) -0.0292(16) 0.0119(14) -0.0070(13) C5 0.057(2) 0.062(2) 0.088(2) -0.0396(19) 0.0172(18) -0.0140(16) C6 0.0549(19) 0.0529(18) 0.072(2) -0.0240(16) 0.0182(16) 0.0041(15) C7 0.0390(15) 0.0522(17) 0.0514(16) -0.0045(13) 0.0098(12) 0.0059(13) C8 0.0352(13) 0.0330(13) 0.0412(13) 0.0013(10) 0.0064(10) -0.0006(10) C9 0.0358(14) 0.0544(17) 0.0566(17) -0.0105(14) 0.0109(12) -0.0051(13) C10 0.0383(16) 0.073(2) 0.084(2) -0.0133(19) 0.0222(16) -0.0011(16) C11 0.059(2) 0.062(2) 0.084(2) -0.0115(18) 0.0357(18) 0.0078(17) C12 0.064(2) 0.0467(17) 0.067(2) -0.0170(15) 0.0230(16) -0.0046(15) C13 0.0310(13) 0.0355(13) 0.0489(14) -0.0071(11) 0.0096(11) -0.0045(10) C14 0.0282(12) 0.0389(13) 0.0438(14) -0.0065(11) 0.0105(10) -0.0031(10) C15 0.0330(13) 0.0377(14) 0.0515(15) -0.0048(12) 0.0129(11) -0.0046(11) C16 0.0515(17) 0.0419(16) 0.0596(17) -0.0029(13) 0.0109(14) -0.0109(13) C17 0.062(2) 0.0389(16) 0.078(2) 0.0113(15) 0.0266(17) 0.0002(14) C18 0.0475(18) 0.061(2) 0.067(2) 0.0111(16) 0.0097(15) 0.0078(15) C19 0.0381(15) 0.0503(17) 0.0651(19) -0.0047(15) 0.0019(13) 0.0019(13) C20 0.0288(12) 0.0422(14) 0.0446(14) -0.0042(11) 0.0139(10) -0.0019(11) C21 0.0396(15) 0.0424(15) 0.0542(16) -0.0037(13) 0.0087(12) -0.0042(12) C22 0.0595(19) 0.0427(16) 0.0658(19) -0.0038(14) 0.0184(16) -0.0094(14) C23 0.061(2) 0.0509(18) 0.068(2) 0.0131(15) 0.0168(17) 0.0031(15) C24 0.0504(18) 0.0589(19) 0.0553(17) 0.0092(15) 0.0077(14) -0.0016(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N7 2.017(2) . ? Cu1 N1 2.053(2) . ? Cu1 N4 2.053(2) . ? Cu1 N10 2.099(2) . ? Cu2 N2 1.934(2) . ? Cu2 N8 1.979(2) 3_666 ? Cu2 N9 2.150(2) 3_666 ? Cu2 N5 2.323(2) . ? N1 C1 1.335(3) . ? N1 N2 1.350(3) . ? N2 C2 1.346(3) . ? N3 C1 1.344(3) . ? N3 C2 1.347(3) . ? N4 C7 1.340(3) . ? N4 C3 1.351(3) . ? N5 C12 1.326(4) . ? N5 C8 1.352(3) . ? N6 C13 1.332(3) . ? N6 N7 1.370(3) . ? N7 C14 1.340(3) . ? N8 C14 1.347(3) . ? N8 C13 1.355(3) . ? N8 Cu2 1.979(2) 3_666 ? N9 C19 1.338(3) . ? N9 C15 1.352(3) . ? N9 Cu2 2.150(2) 3_666 ? N10 C24 1.339(4) . ? N10 C20 1.356(3) . ? C1 C3 1.464(3) . ? C2 C8 1.454(4) . ? C3 C4 1.384(3) . ? C4 C5 1.378(4) . ? C5 C6 1.368(5) . ? C6 C7 1.374(4) . ? C8 C9 1.383(4) . ? C9 C10 1.373(4) . ? C10 C11 1.374(5) . ? C11 C12 1.380(5) . ? C13 C15 1.466(4) . ? C14 C20 1.456(4) . ? C15 C16 1.379(4) . ? C16 C17 1.385(4) . ? C17 C18 1.374(4) . ? C18 C19 1.377(4) . ? C20 C21 1.385(4) . ? C21 C22 1.380(4) . ? C22 C23 1.373(4) . ? C23 C24 1.374(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 N7 Cu1 N1 128.77(9) . . ? N7 Cu1 N4 120.88(9) . . ? N1 Cu1 N4 80.74(8) . . ? N7 Cu1 N10 81.55(9) . . ? N1 Cu1 N10 103.98(9) . . ? N4 Cu1 N10 147.60(9) . . ? N2 Cu2 N8 138.08(9) . 3_666 ? N2 Cu2 N9 126.40(9) . 3_666 ? N8 Cu2 N9 80.83(8) 3_666 3_666 ? N2 Cu2 N5 77.35(9) . . ? N8 Cu2 N5 134.01(9) 3_666 . ? N9 Cu2 N5 100.37(8) 3_666 . ? C1 N1 N2 105.8(2) . . ? C1 N1 Cu1 112.42(17) . . ? N2 N1 Cu1 141.45(16) . . ? C2 N2 N1 105.7(2) . . ? C2 N2 Cu2 119.53(18) . . ? N1 N2 Cu2 134.69(16) . . ? C1 N3 C2 101.1(2) . . ? C7 N4 C3 117.3(2) . . ? C7 N4 Cu1 128.02(18) . . ? C3 N4 Cu1 113.43(16) . . ? C12 N5 C8 117.5(2) . . ? C12 N5 Cu2 133.6(2) . . ? C8 N5 Cu2 108.58(17) . . ? C13 N6 N7 104.5(2) . . ? C14 N7 N6 106.9(2) . . ? C14 N7 Cu1 111.89(17) . . ? N6 N7 Cu1 141.13(16) . . ? C14 N8 C13 101.6(2) . . ? C14 N8 Cu2 144.31(18) . 3_666 ? C13 N8 Cu2 113.90(16) . 3_666 ? C19 N9 C15 117.8(2) . . ? C19 N9 Cu2 130.16(19) . 3_666 ? C15 N9 Cu2 111.83(17) . 3_666 ? C24 N10 C20 117.2(2) . . ? C24 N10 Cu1 128.50(19) . . ? C20 N10 Cu1 111.07(17) . . ? N1 C1 N3 114.0(2) . . ? N1 C1 C3 118.1(2) . . ? N3 C1 C3 127.9(2) . . ? N2 C2 N3 113.4(2) . . ? N2 C2 C8 119.1(2) . . ? N3 C2 C8 127.5(2) . . ? N4 C3 C4 122.1(2) . . ? N4 C3 C1 114.8(2) . . ? C4 C3 C1 123.0(2) . . ? C5 C4 C3 119.0(3) . . ? C6 C5 C4 119.4(3) . . ? C5 C6 C7 118.6(3) . . ? N4 C7 C6 123.6(3) . . ? N5 C8 C9 121.6(3) . . ? N5 C8 C2 114.8(2) . . ? C9 C8 C2 123.6(2) . . ? C10 C9 C8 119.9(3) . . ? C9 C10 C11 118.7(3) . . ? C10 C11 C12 118.4(3) . . ? N5 C12 C11 124.0(3) . . ? N6 C13 N8 114.3(2) . . ? N6 C13 C15 125.9(2) . . ? N8 C13 C15 119.8(2) . . ? N7 C14 N8 112.6(2) . . ? N7 C14 C20 119.7(2) . . ? N8 C14 C20 127.6(2) . . ? N9 C15 C16 122.3(3) . . ? N9 C15 C13 113.4(2) . . ? C16 C15 C13 124.3(2) . . ? C15 C16 C17 119.0(3) . . ? C18 C17 C16 118.9(3) . . ? C17 C18 C19 119.1(3) . . ? N9 C19 C18 122.9(3) . . ? N10 C20 C21 122.0(2) . . ? N10 C20 C14 114.3(2) . . ? C21 C20 C14 123.5(2) . . ? C22 C21 C20 119.3(3) . . ? C23 C22 C21 118.9(3) . . ? C22 C23 C24 118.8(3) . . ? N10 C24 C23 123.7(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.405 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.063 #===============================END data_isomer_II _database_code_depnum_ccdc_archive 'CCDC 246256' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cu N5' _chemical_formula_weight 285.77 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.2147(11) _cell_length_b 18.5212(12) _cell_length_c 12.5482(8) _cell_angle_alpha 90.00 _cell_angle_beta 115.5060(10) _cell_angle_gamma 90.00 _cell_volume 3401.2(4) _cell_formula_units_Z 12 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 1.913 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5150 _exptl_absorpt_correction_T_max 0.7756 _exptl_absorpt_process_details 'Bruker SADABS' _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 Apex CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11455 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3806 _reflns_number_gt 3062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART for Windows NT, Bruker AXS Inc., 1998.' _computing_cell_refinement 'SAINT-PLUS for Windows NT, Ver. 6.0' _computing_data_reduction 'SAINT-PLUS for Windows NT, Ver. 6.0' _computing_structure_solution 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_publication_material 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _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^)+(0.0482P)^2^+1.8529P] 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 3806 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.0000 0.01754(2) 0.7500 0.04623(14) Uani 1 2 d S . . Cu2 Cu 0.03856(2) 0.244952(16) 1.11147(3) 0.04671(12) Uani 1 1 d . . . N1 N 0.11441(12) 0.09823(10) 1.08369(17) 0.0351(4) Uani 1 1 d . . . N2 N 0.05676(13) 0.15604(10) 1.04388(17) 0.0342(4) Uani 1 1 d . . . N3 N 0.01676(11) 0.07909(9) 0.89348(16) 0.0291(4) Uani 1 1 d . . . N4 N 0.10056(13) -0.04309(10) 0.87757(17) 0.0354(4) Uani 1 1 d . . . N5 N -0.07519(15) 0.25239(10) 0.9245(2) 0.0438(5) Uani 1 1 d . . . N6 N 0.02131(14) 0.31530(9) 1.21330(17) 0.0362(4) Uani 1 1 d . . . N7 N 0.0000 0.43071(14) 1.2500 0.0390(7) Uani 1 2 d S . . N8 N 0.08911(16) 0.35120(11) 1.0580(2) 0.0486(5) Uani 1 1 d . . . C1 C 0.08797(14) 0.05426(11) 0.99149(19) 0.0279(4) Uani 1 1 d . . . C2 C 0.00021(14) 0.14271(11) 0.93123(19) 0.0296(5) Uani 1 1 d . . . C3 C 0.12880(14) -0.01558(11) 0.98745(19) 0.0285(4) Uani 1 1 d . . . C4 C 0.19081(15) -0.05129(13) 1.0862(2) 0.0370(5) Uani 1 1 d . . . H4A H 0.2100 -0.0308 1.1607 0.044 Uiso 1 1 calc R . . C5 C 0.22387(16) -0.11761(13) 1.0730(2) 0.0438(6) Uani 1 1 d . . . H5A H 0.2664 -0.1422 1.1381 0.053 Uiso 1 1 calc R . . C6 C 0.19271(18) -0.14692(13) 0.9612(3) 0.0472(6) Uani 1 1 d . . . H6A H 0.2126 -0.1922 0.9502 0.057 Uiso 1 1 calc R . . C7 C 0.13230(19) -0.10842(13) 0.8670(2) 0.0453(6) Uani 1 1 d . . . H7A H 0.1122 -0.1284 0.7920 0.054 Uiso 1 1 calc R . . C8 C -0.07095(15) 0.19449(12) 0.8622(2) 0.0335(5) Uani 1 1 d . . . C9 C -0.12976(17) 0.18545(14) 0.7445(2) 0.0453(6) Uani 1 1 d . . . H9A H -0.1253 0.1454 0.7026 0.054 Uiso 1 1 calc R . . C10 C -0.1958(2) 0.23818(17) 0.6905(3) 0.0586(8) Uani 1 1 d . . . H10A H -0.2373 0.2332 0.6118 0.070 Uiso 1 1 calc R . . C11 C -0.1996(2) 0.29753(18) 0.7538(3) 0.0645(9) Uani 1 1 d . . . H11A H -0.2431 0.3334 0.7189 0.077 Uiso 1 1 calc R . . C12 C -0.1383(2) 0.30233(16) 0.8685(3) 0.0589(8) Uani 1 1 d . . . H12A H -0.1403 0.3430 0.9108 0.071 Uiso 1 1 calc R . . C13 C 0.03275(15) 0.38518(11) 1.1948(2) 0.0339(5) Uani 1 1 d . . . C14 C 0.07689(16) 0.40566(12) 1.1196(2) 0.0366(5) Uani 1 1 d . . . C15 C 0.1034(2) 0.47552(14) 1.1101(3) 0.0557(7) Uani 1 1 d . . . H15A H 0.0948 0.5127 1.1541 0.067 Uiso 1 1 calc R . . C16 C 0.1426(2) 0.48883(16) 1.0342(3) 0.0675(9) Uani 1 1 d . . . H16A H 0.1626 0.5351 1.0282 0.081 Uiso 1 1 calc R . . C17 C 0.1521(2) 0.43408(17) 0.9680(3) 0.0632(8) Uani 1 1 d . . . H17A H 0.1765 0.4425 0.9143 0.076 Uiso 1 1 calc R . . C18 C 0.1248(2) 0.36622(17) 0.9825(3) 0.0612(8) Uani 1 1 d . . . H18A H 0.1315 0.3288 0.9374 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0665(3) 0.0358(2) 0.0242(2) 0.000 0.0080(2) 0.000 Cu2 0.0671(2) 0.03248(18) 0.0453(2) -0.00946(13) 0.02872(18) 0.00345(13) N1 0.0427(10) 0.0279(9) 0.0302(11) -0.0012(8) 0.0114(9) 0.0014(8) N2 0.0453(11) 0.0262(9) 0.0306(11) -0.0004(8) 0.0158(9) 0.0037(8) N3 0.0337(9) 0.0266(9) 0.0261(10) 0.0003(7) 0.0120(8) 0.0017(7) N4 0.0480(11) 0.0288(9) 0.0307(11) 0.0002(8) 0.0179(9) 0.0041(8) N5 0.0511(13) 0.0330(11) 0.0534(15) 0.0029(9) 0.0284(11) 0.0106(9) N6 0.0573(12) 0.0268(9) 0.0322(11) 0.0001(8) 0.0266(10) 0.0001(8) N7 0.0562(17) 0.0252(13) 0.0438(18) 0.000 0.0292(15) 0.000 N8 0.0699(14) 0.0375(11) 0.0553(15) -0.0010(10) 0.0428(13) -0.0037(10) C1 0.0342(11) 0.0246(10) 0.0249(11) 0.0003(8) 0.0129(9) -0.0025(8) C2 0.0358(11) 0.0275(11) 0.0286(12) 0.0006(9) 0.0170(9) -0.0001(8) C3 0.0322(11) 0.0255(10) 0.0306(12) 0.0010(9) 0.0162(9) -0.0019(8) C4 0.0352(12) 0.0388(12) 0.0335(13) 0.0061(10) 0.0113(10) 0.0002(9) C5 0.0398(13) 0.0424(14) 0.0502(16) 0.0208(12) 0.0202(12) 0.0110(11) C6 0.0589(16) 0.0350(13) 0.0593(18) 0.0112(12) 0.0364(14) 0.0149(11) C7 0.0690(17) 0.0332(12) 0.0398(15) -0.0017(11) 0.0293(13) 0.0070(11) C8 0.0366(11) 0.0309(11) 0.0385(14) 0.0068(10) 0.0215(10) 0.0020(9) C9 0.0450(14) 0.0506(15) 0.0396(15) 0.0081(12) 0.0174(12) 0.0065(11) C10 0.0471(16) 0.073(2) 0.0515(18) 0.0230(15) 0.0171(14) 0.0083(14) C11 0.0534(17) 0.0596(19) 0.086(3) 0.0325(18) 0.0351(18) 0.0241(15) C12 0.0628(18) 0.0448(16) 0.080(2) 0.0110(15) 0.0408(18) 0.0199(13) C13 0.0456(13) 0.0251(10) 0.0322(13) 0.0010(9) 0.0179(10) -0.0005(9) C14 0.0429(12) 0.0326(12) 0.0362(13) 0.0027(10) 0.0189(11) -0.0016(10) C15 0.080(2) 0.0364(13) 0.065(2) -0.0041(13) 0.0451(17) -0.0121(13) C16 0.094(2) 0.0437(16) 0.087(3) 0.0000(16) 0.059(2) -0.0218(15) C17 0.076(2) 0.0657(19) 0.070(2) 0.0111(16) 0.0518(18) -0.0051(16) C18 0.082(2) 0.0551(17) 0.070(2) -0.0034(15) 0.0547(19) -0.0035(15) _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 N3 2.0478(18) . ? Cu1 N3 2.0478(18) 2_556 ? Cu1 N4 2.0576(19) 2_556 ? Cu1 N4 2.0576(19) . ? Cu2 N6 1.9278(18) . ? Cu2 N2 1.9324(18) . ? Cu2 N5 2.280(2) . ? Cu2 N8 2.338(2) . ? N1 C1 1.326(3) . ? N1 N2 1.367(2) . ? N2 C2 1.335(3) . ? N3 C2 1.340(3) . ? N3 C1 1.354(3) . ? N4 C7 1.344(3) . ? N4 C3 1.352(3) . ? N5 C12 1.333(3) . ? N5 C8 1.346(3) . ? N6 C13 1.342(3) . ? N6 N6 1.369(4) 2_557 ? N7 C13 1.338(3) . ? N7 C13 1.338(3) 2_557 ? N8 C18 1.335(3) . ? N8 C14 1.336(3) . ? C1 C3 1.464(3) . ? C2 C8 1.463(3) . ? C3 C4 1.382(3) . ? C4 C5 1.379(3) . ? C5 C6 1.381(4) . ? C6 C7 1.367(4) . ? C8 C9 1.381(4) . ? C9 C10 1.391(4) . ? C10 C11 1.373(5) . ? C11 C12 1.355(5) . ? C13 C14 1.459(3) . ? C14 C15 1.384(3) . ? C15 C16 1.376(4) . ? C16 C17 1.361(4) . ? C17 C18 1.370(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 N3 Cu1 N3 112.35(10) . 2_556 ? N3 Cu1 N4 138.45(7) . 2_556 ? N3 Cu1 N4 81.90(7) 2_556 2_556 ? N3 Cu1 N4 81.90(7) . . ? N3 Cu1 N4 138.45(7) 2_556 . ? N4 Cu1 N4 113.85(11) 2_556 . ? N6 Cu2 N2 163.76(8) . . ? N6 Cu2 N5 110.94(8) . . ? N2 Cu2 N5 78.97(8) . . ? N6 Cu2 N8 77.89(7) . . ? N2 Cu2 N8 116.91(8) . . ? N5 Cu2 N8 83.23(8) . . ? C1 N1 N2 104.41(17) . . ? C2 N2 N1 106.97(17) . . ? C2 N2 Cu2 117.20(15) . . ? N1 N2 Cu2 135.80(15) . . ? C2 N3 C1 101.52(17) . . ? C2 N3 Cu1 146.06(15) . . ? C1 N3 Cu1 110.36(13) . . ? C7 N4 C3 117.7(2) . . ? C7 N4 Cu1 128.57(17) . . ? C3 N4 Cu1 113.25(14) . . ? C12 N5 C8 117.8(3) . . ? C12 N5 Cu2 133.0(2) . . ? C8 N5 Cu2 109.17(15) . . ? C13 N6 N6 105.29(12) . 2_557 ? C13 N6 Cu2 117.84(15) . . ? N6 N6 Cu2 134.85(8) 2_557 . ? C13 N7 C13 101.8(2) . 2_557 ? C18 N8 C14 118.1(2) . . ? C18 N8 Cu2 133.75(19) . . ? C14 N8 Cu2 108.17(15) . . ? N1 C1 N3 114.38(18) . . ? N1 C1 C3 126.28(19) . . ? N3 C1 C3 119.34(19) . . ? N2 C2 N3 112.71(19) . . ? N2 C2 C8 120.82(19) . . ? N3 C2 C8 126.5(2) . . ? N4 C3 C4 122.0(2) . . ? N4 C3 C1 114.13(19) . . ? C4 C3 C1 123.8(2) . . ? C5 C4 C3 119.3(2) . . ? C4 C5 C6 118.8(2) . . ? C7 C6 C5 119.1(2) . . ? N4 C7 C6 123.1(2) . . ? N5 C8 C9 122.2(2) . . ? N5 C8 C2 113.8(2) . . ? C9 C8 C2 124.0(2) . . ? C8 C9 C10 117.9(3) . . ? C11 C10 C9 119.9(3) . . ? C12 C11 C10 118.1(3) . . ? N5 C12 C11 124.1(3) . . ? N7 C13 N6 113.8(2) . . ? N7 C13 C14 125.8(2) . . ? N6 C13 C14 120.4(2) . . ? N8 C14 C15 121.8(2) . . ? N8 C14 C13 114.4(2) . . ? C15 C14 C13 123.7(2) . . ? C16 C15 C14 118.6(3) . . ? C17 C16 C15 119.8(3) . . ? C16 C17 C18 118.3(3) . . ? N8 C18 C17 123.3(3) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.339 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.067 #===============================END data_isomer_III _database_code_depnum_ccdc_archive 'CCDC 246257' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cu N5' _chemical_formula_weight 285.77 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)/c 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 11.6326(9) _cell_length_b 9.6838(7) _cell_length_c 11.1798(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.410(2) _cell_angle_gamma 90.00 _cell_volume 1194.93(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 1.815 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6120 _exptl_absorpt_correction_T_max 0.8394 _exptl_absorpt_process_details 'Bruker SADABS' _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 Apex CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9255 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2874 _reflns_number_gt 2277 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART for Windows NT, Bruker AXS Inc., 1998.' _computing_cell_refinement 'SAINT-PLUS for Windows NT, Ver. 6.0' _computing_data_reduction 'SAINT-PLUS for Windows NT, Ver. 6.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_publication_material 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _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^)+(0.0521P)^2^+0.4361P] 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 2874 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.82953(3) 0.14189(4) 0.75170(3) 0.05323(15) Uani 1 1 d . . . N1 N 0.69089(16) 0.13401(19) 1.03940(18) 0.0374(4) Uani 1 1 d . . . N2 N 0.78036(16) 0.22363(19) 1.10195(16) 0.0349(4) Uani 1 1 d . . . N3 N 0.81965(16) 0.16030(18) 0.92686(17) 0.0351(4) Uani 1 1 d . . . N4 N 0.68705(19) -0.0017(2) 0.73718(19) 0.0511(5) Uani 1 1 d . . . N5 N 0.97700(18) 0.3831(2) 1.18985(19) 0.0404(4) Uani 1 1 d . . . C1 C 0.71851(18) 0.0984(2) 0.9369(2) 0.0335(4) Uani 1 1 d . . . C2 C 0.85527(18) 0.2357(2) 1.03278(19) 0.0336(4) Uani 1 1 d . . . C3 C 0.64894(19) 0.0049(2) 0.8387(2) 0.0384(5) Uani 1 1 d . . . C4 C 0.5497(2) -0.0702(3) 0.8465(3) 0.0548(7) Uani 1 1 d . . . H4A H 0.5253 -0.0641 0.9179 0.066 Uiso 1 1 calc R . . C5 C 0.4884(3) -0.1532(3) 0.7478(4) 0.0729(10) Uani 1 1 d . . . H5A H 0.4213 -0.2034 0.7509 0.087 Uiso 1 1 calc R . . C6 C 0.5271(3) -0.1612(4) 0.6441(4) 0.0894(13) Uani 1 1 d . . . H6A H 0.4879 -0.2180 0.5765 0.107 Uiso 1 1 calc R . . C7 C 0.6251(3) -0.0835(4) 0.6429(3) 0.0811(11) Uani 1 1 d . . . H7A H 0.6500 -0.0880 0.5717 0.097 Uiso 1 1 calc R . . C8 C 0.9674(2) 0.3137(2) 1.0830(2) 0.0396(5) Uani 1 1 d . . . C9 C 1.0599(3) 0.3104(4) 1.0305(3) 0.0717(10) Uani 1 1 d . . . H9A H 1.0505 0.2631 0.9556 0.086 Uiso 1 1 calc R . . C10 C 1.1657(3) 0.3779(4) 1.0905(4) 0.0974(15) Uani 1 1 d . . . H10A H 1.2295 0.3761 1.0573 0.117 Uiso 1 1 calc R . . C11 C 1.1770(3) 0.4486(4) 1.2006(3) 0.0796(11) Uani 1 1 d . . . H11A H 1.2481 0.4951 1.2428 0.096 Uiso 1 1 calc R . . C12 C 1.0814(2) 0.4485(3) 1.2459(3) 0.0567(7) Uani 1 1 d . . . H12A H 1.0890 0.4966 1.3200 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0578(2) 0.0744(3) 0.0378(2) 0.00241(14) 0.02987(16) -0.00990(16) N1 0.0332(9) 0.0505(11) 0.0319(10) 0.0022(8) 0.0151(8) -0.0014(8) N2 0.0324(9) 0.0476(10) 0.0276(9) 0.0009(8) 0.0136(7) 0.0000(8) N3 0.0347(9) 0.0480(10) 0.0265(9) -0.0009(7) 0.0151(7) -0.0055(8) N4 0.0512(12) 0.0674(14) 0.0411(12) -0.0134(10) 0.0239(10) -0.0213(10) N5 0.0405(10) 0.0518(11) 0.0328(10) -0.0056(8) 0.0173(8) -0.0074(8) C1 0.0299(10) 0.0427(11) 0.0302(11) 0.0042(9) 0.0128(8) -0.0010(8) C2 0.0327(10) 0.0429(11) 0.0274(10) 0.0014(8) 0.0128(8) -0.0005(9) C3 0.0359(11) 0.0460(12) 0.0363(12) -0.0018(9) 0.0157(9) -0.0046(9) C4 0.0506(14) 0.0624(16) 0.0619(17) -0.0124(14) 0.0328(13) -0.0174(13) C5 0.0573(17) 0.084(2) 0.087(2) -0.0339(18) 0.0370(17) -0.0363(16) C6 0.081(2) 0.117(3) 0.080(3) -0.054(2) 0.039(2) -0.055(2) C7 0.084(2) 0.115(3) 0.0588(19) -0.041(2) 0.0430(17) -0.049(2) C8 0.0379(12) 0.0513(12) 0.0350(12) -0.0056(10) 0.0192(10) -0.0067(10) C9 0.0580(17) 0.110(2) 0.0638(19) -0.0436(18) 0.0421(15) -0.0356(17) C10 0.064(2) 0.153(4) 0.098(3) -0.063(3) 0.058(2) -0.054(2) C11 0.0572(18) 0.113(3) 0.077(2) -0.046(2) 0.0331(17) -0.0428(18) C12 0.0589(16) 0.0693(17) 0.0464(15) -0.0196(13) 0.0229(13) -0.0216(14) _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 N3 2.0055(18) . ? Cu1 N2 2.0545(18) 4_565 ? Cu1 N5 2.0563(19) 4_565 ? Cu1 N4 2.130(2) . ? N1 C1 1.329(3) . ? N1 N2 1.366(3) . ? N2 C2 1.340(2) . ? N2 Cu1 2.0545(18) 4_566 ? N3 C2 1.341(3) . ? N3 C1 1.356(3) . ? N4 C7 1.333(3) . ? N4 C3 1.344(3) . ? N5 C12 1.337(3) . ? N5 C8 1.344(3) . ? N5 Cu1 2.0563(19) 4_566 ? C1 C3 1.456(3) . ? C2 C8 1.457(3) . ? C3 C4 1.390(3) . ? C4 C5 1.370(4) . ? C5 C6 1.371(5) . ? C6 C7 1.370(4) . ? C8 C9 1.379(3) . ? C9 C10 1.368(4) . ? C10 C11 1.377(5) . ? C11 C12 1.360(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 N3 Cu1 N2 130.71(7) . 4_565 ? N3 Cu1 N5 130.54(8) . 4_565 ? N2 Cu1 N5 81.24(7) 4_565 4_565 ? N3 Cu1 N4 81.33(7) . . ? N2 Cu1 N4 110.00(8) 4_565 . ? N5 Cu1 N4 127.54(9) 4_565 . ? C1 N1 N2 104.69(17) . . ? C2 N2 N1 106.81(17) . . ? C2 N2 Cu1 110.50(14) . 4_566 ? N1 N2 Cu1 142.28(14) . 4_566 ? C2 N3 C1 101.63(17) . . ? C2 N3 Cu1 144.47(14) . . ? C1 N3 Cu1 111.13(14) . . ? C7 N4 C3 117.1(2) . . ? C7 N4 Cu1 131.40(19) . . ? C3 N4 Cu1 111.16(15) . . ? C12 N5 C8 117.5(2) . . ? C12 N5 Cu1 128.94(17) . 4_566 ? C8 N5 Cu1 113.34(15) . 4_566 ? N1 C1 N3 114.15(19) . . ? N1 C1 C3 125.68(19) . . ? N3 C1 C3 120.15(19) . . ? N2 C2 N3 112.71(18) . . ? N2 C2 C8 119.27(19) . . ? N3 C2 C8 127.71(18) . . ? N4 C3 C4 122.0(2) . . ? N4 C3 C1 114.42(19) . . ? C4 C3 C1 123.6(2) . . ? C5 C4 C3 119.2(3) . . ? C4 C5 C6 119.2(3) . . ? C7 C6 C5 118.3(3) . . ? N4 C7 C6 124.2(3) . . ? N5 C8 C9 122.2(2) . . ? N5 C8 C2 114.46(19) . . ? C9 C8 C2 123.2(2) . . ? C10 C9 C8 118.8(3) . . ? C9 C10 C11 119.5(3) . . ? C12 C11 C10 118.3(3) . . ? N5 C12 C11 123.6(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.407 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.061 #===============================END data_isomer_IV _database_code_depnum_ccdc_archive 'CCDC 246258' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cu N5' _chemical_formula_weight 285.77 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 tetrahedral _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 11.5320(10) _cell_length_b 11.5320(10) _cell_length_c 18.2900(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2432.3(3) _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 needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.783 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5506 _exptl_absorpt_correction_T_max 0.7396 _exptl_absorpt_process_details 'Bruker SADABS' _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 Apex CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15744 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2934 _reflns_number_gt 2478 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART for Windows NT, Bruker AXS Inc., 1998.' _computing_cell_refinement 'SAINT-PLUS for Windows NT, Ver. 6.0' _computing_data_reduction 'SAINT-PLUS for Windows NT, Ver. 6.0' _computing_structure_solution 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _computing_publication_material 'SHELXTL Ver. 6.10, (Sheldrick, 2000)' _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^)+(0.0436P)^2^+0.4635P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.001(17) _refine_ls_number_reflns 2934 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.59866(4) 0.21505(4) 0.039964(19) 0.05530(15) Uani 1 1 d . . . N1 N 0.67826(19) 0.08112(19) 0.09061(11) 0.0373(5) Uani 1 1 d . . . N2 N 0.7473(2) -0.0128(2) 0.07708(12) 0.0380(5) Uani 1 1 d . . . N3 N 0.7115(2) -0.00468(18) 0.19813(11) 0.0358(5) Uani 1 1 d . . . N4 N 0.5378(2) 0.2464(2) 0.14557(12) 0.0419(5) Uani 1 1 d . . . N5 N 0.8402(2) -0.1924(2) 0.22920(13) 0.0463(6) Uani 1 1 d . . . C1 C 0.6586(2) 0.0831(2) 0.16297(13) 0.0347(5) Uani 1 1 d . . . C2 C 0.7658(2) -0.0603(2) 0.14266(13) 0.0344(5) Uani 1 1 d . . . C3 C 0.5873(2) 0.1742(2) 0.19481(14) 0.0396(6) Uani 1 1 d . . . C4 C 0.5699(3) 0.1875(3) 0.26947(15) 0.0583(8) Uani 1 1 d . . . H4A H 0.6060 0.1383 0.3027 0.070 Uiso 1 1 calc R . . C5 C 0.4984(4) 0.2749(4) 0.29309(19) 0.0758(12) Uani 1 1 d . . . H5A H 0.4863 0.2860 0.3429 0.091 Uiso 1 1 calc R . . C6 C 0.4450(4) 0.3455(3) 0.2437(2) 0.0696(11) Uani 1 1 d . . . H6A H 0.3948 0.4038 0.2589 0.084 Uiso 1 1 calc R . . C7 C 0.4676(3) 0.3280(3) 0.17049(18) 0.0566(8) Uani 1 1 d . . . H7A H 0.4314 0.3763 0.1368 0.068 Uiso 1 1 calc R . . C8 C 0.8404(2) -0.1596(3) 0.15826(15) 0.0410(6) Uani 1 1 d . . . C9 C 0.9082(3) -0.2137(3) 0.10565(18) 0.0564(8) Uani 1 1 d . . . H9A H 0.9041 -0.1916 0.0568 0.068 Uiso 1 1 calc R . . C10 C 0.9820(3) -0.3013(4) 0.1277(2) 0.0766(12) Uani 1 1 d . . . H10A H 1.0287 -0.3389 0.0936 0.092 Uiso 1 1 calc R . . C11 C 0.9860(4) -0.3329(4) 0.2000(2) 0.0811(13) Uani 1 1 d . . . H11A H 1.0371 -0.3898 0.2162 0.097 Uiso 1 1 calc R . . C12 C 0.9120(3) -0.2777(3) 0.2481(2) 0.0649(9) Uani 1 1 d . . . H12A H 0.9124 -0.3016 0.2967 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0710(3) 0.0653(3) 0.02962(17) 0.01344(16) -0.01141(17) -0.0063(2) N1 0.0459(12) 0.0424(12) 0.0236(9) 0.0021(8) 0.0006(8) -0.0021(10) N2 0.0443(12) 0.0416(12) 0.0282(10) 0.0008(9) 0.0050(9) -0.0037(9) N3 0.0398(11) 0.0422(11) 0.0255(10) 0.0046(9) 0.0025(9) 0.0023(10) N4 0.0492(13) 0.0431(12) 0.0333(12) 0.0026(10) -0.0069(10) 0.0048(11) N5 0.0486(13) 0.0522(14) 0.0381(12) 0.0053(10) 0.0061(10) 0.0125(11) C1 0.0388(13) 0.0399(14) 0.0255(11) 0.0012(10) 0.0011(10) -0.0034(11) C2 0.0362(13) 0.0388(13) 0.0283(11) 0.0004(10) 0.0065(10) -0.0056(11) C3 0.0438(14) 0.0439(13) 0.0312(12) 0.0016(10) -0.0017(11) 0.0035(12) C4 0.078(2) 0.068(2) 0.0292(13) 0.0005(13) -0.0018(13) 0.0275(17) C5 0.101(3) 0.089(3) 0.0370(15) -0.0077(17) 0.0022(18) 0.040(2) C6 0.083(3) 0.071(2) 0.0549(19) -0.0112(17) -0.0006(18) 0.037(2) C7 0.063(2) 0.0575(19) 0.0491(18) 0.0035(15) -0.0072(15) 0.0190(16) C8 0.0397(14) 0.0469(15) 0.0364(14) 0.0036(12) 0.0083(11) 0.0003(12) C9 0.0606(19) 0.0644(19) 0.0443(16) 0.0007(15) 0.0134(14) 0.0103(17) C10 0.072(2) 0.084(3) 0.074(3) -0.004(2) 0.026(2) 0.034(2) C11 0.076(3) 0.086(3) 0.081(3) 0.009(2) 0.006(2) 0.042(2) C12 0.072(2) 0.070(2) 0.0527(19) 0.0119(16) 0.0049(17) 0.0229(19) _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 N3 1.999(2) 3_544 ? Cu1 N1 2.021(2) . ? Cu1 N4 2.087(2) . ? Cu1 N5 2.118(2) 3_544 ? N1 C1 1.343(3) . ? N1 N2 1.367(3) . ? N2 C2 1.336(3) . ? N3 C1 1.346(3) . ? N3 C2 1.354(3) . ? N3 Cu1 1.999(2) 4 ? N4 C7 1.322(4) . ? N4 C3 1.353(3) . ? N5 C12 1.332(4) . ? N5 C8 1.352(4) . ? N5 Cu1 2.118(2) 4 ? C1 C3 1.455(4) . ? C2 C8 1.460(4) . ? C3 C4 1.389(4) . ? C4 C5 1.372(5) . ? C5 C6 1.363(5) . ? C6 C7 1.378(5) . ? C8 C9 1.389(4) . ? C9 C10 1.380(5) . ? C10 C11 1.373(5) . ? C11 C12 1.381(5) . ? 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 N3 Cu1 N1 127.98(9) 3_544 . ? N3 Cu1 N4 126.80(9) 3_544 . ? N1 Cu1 N4 82.01(9) . . ? N3 Cu1 N5 81.37(9) 3_544 3_544 ? N1 Cu1 N5 121.96(9) . 3_544 ? N4 Cu1 N5 122.62(10) . 3_544 ? C1 N1 N2 106.9(2) . . ? C1 N1 Cu1 111.20(17) . . ? N2 N1 Cu1 141.91(16) . . ? C2 N2 N1 104.8(2) . . ? C1 N3 C2 102.0(2) . . ? C1 N3 Cu1 144.95(18) . 4 ? C2 N3 Cu1 111.28(17) . 4 ? C7 N4 C3 117.8(2) . . ? C7 N4 Cu1 130.4(2) . . ? C3 N4 Cu1 111.55(18) . . ? C12 N5 C8 117.1(3) . . ? C12 N5 Cu1 131.7(2) . 4 ? C8 N5 Cu1 111.22(18) . 4 ? N1 C1 N3 112.4(2) . . ? N1 C1 C3 120.2(2) . . ? N3 C1 C3 127.4(2) . . ? N2 C2 N3 113.9(2) . . ? N2 C2 C8 126.2(2) . . ? N3 C2 C8 119.8(2) . . ? N4 C3 C4 121.7(3) . . ? N4 C3 C1 114.6(2) . . ? C4 C3 C1 123.7(2) . . ? C5 C4 C3 118.6(3) . . ? C6 C5 C4 120.1(3) . . ? C5 C6 C7 118.1(3) . . ? N4 C7 C6 123.7(3) . . ? N5 C8 C9 122.7(3) . . ? N5 C8 C2 114.0(2) . . ? C9 C8 C2 123.3(3) . . ? C10 C9 C8 118.3(3) . . ? C11 C10 C9 119.7(3) . . ? C10 C11 C12 118.1(3) . . ? N5 C12 C11 124.0(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.511 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.060 #===============================END