# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Hee Cheul Choi' _publ_contact_author_email CHOIHC@POSTECH.EDU _publ_section_title ; Single Crystal Structure of Copper Hexadecafluorophthalocyanine (F16CuPc) Ribbon ; loop_ _publ_author_name 'Hee Cheul Choi' 'In Chul Hwang' 'Kwang S. Kim' 'Hyun Jae Song' 'Seok Min Yoon' # Attachment 'F16CuPc-third.cif' data_F16CuPc _database_code_depnum_ccdc_archive 'CCDC 698474' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Copper hexadecafluorophthalocyanine' ; _chemical_name_common "'Copper hexadecafluorophthalocyanine'" _chemical_melting_point ? _chemical_formula_moiety 'C32 Cu F16 N8' _chemical_formula_sum 'C32 Cu F16 N8' _chemical_formula_weight 863.94 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.7960(10) _cell_length_b 10.228(2) _cell_length_c 28.002(6) _cell_angle_alpha 86.41(3) _cell_angle_beta 87.89(3) _cell_angle_gamma 81.39(3) _cell_volume 1354.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _exptl_crystal_description ribbon _exptl_crystal_colour violet _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.010 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 842 _exptl_absorpt_coefficient_mu 0.964 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.8000 _diffrn_radiation_type synchrotron _diffrn_radiation_source white-beam _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum 210' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 19.5 _diffrn_reflns_number 5204 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 29.36 _reflns_number_total 5204 _reflns_number_gt 2410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ADSC Quantum software' _computing_cell_refinement 'DENZO (Z. Otwinowski and W. Minor, 1997)' _computing_data_reduction 'HKL2000 (Z. Otwinowski and W. Minor, 1997)' _computing_structure_solution 'SHELXTL v.6.10 (Bruker-AXS, 2000)' _computing_structure_refinement 'SHELXTL v.6.10 (Bruker-AXS, 2000)' _computing_molecular_graphics 'SHELXTL v.6.10 (Bruker-AXS, 2000)' _computing_publication_material 'SHELXTL v.6.10 (Bruker-AXS, 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^)+(0.1135P)^2^+43.2878P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5204 _refine_ls_number_parameters 517 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0992 _refine_ls_R_factor_gt 0.0981 _refine_ls_wR_factor_ref 0.2101 _refine_ls_wR_factor_gt 0.2041 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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 0.0000 0.0000 0.5000 0.0413(11) Uani 1 2 d S . . F1 F -0.755(2) -0.2707(12) 0.3832(4) 0.057(3) Uani 1 1 d . . . F2 F -0.823(2) -0.2051(12) 0.2886(4) 0.065(3) Uani 1 1 d . . . F3 F -0.564(2) -0.0173(13) 0.2435(5) 0.072(4) Uani 1 1 d . . . F4 F -0.211(2) 0.1103(12) 0.2903(4) 0.064(3) Uani 1 1 d . . . F5 F 0.261(2) 0.3438(11) 0.3254(4) 0.058(3) Uani 1 1 d . . . F6 F 0.610(2) 0.5320(12) 0.3296(5) 0.067(3) Uani 1 1 d . . . F7 F 0.857(2) 0.5634(10) 0.4101(5) 0.060(3) Uani 1 1 d . . . F8 F 0.775(2) 0.4149(10) 0.4911(4) 0.054(3) Uani 1 1 d . . . N1 N -0.172(3) -0.0276(17) 0.4406(7) 0.049(5) Uani 1 1 d . . . N2 N 0.016(3) 0.1320(16) 0.3862(6) 0.045(4) Uani 1 1 d . . . N3 N 0.190(3) 0.1387(14) 0.4661(6) 0.042(4) Uani 1 1 d . . . N4 N 0.450(3) 0.2020(15) 0.5321(7) 0.038(4) Uani 1 1 d . . . C1 C -0.355(4) -0.124(2) 0.4364(8) 0.046(5) Uani 1 1 d . . . C2 C -0.439(4) -0.108(2) 0.3852(8) 0.052(6) Uani 1 1 d . . . C3 C -0.612(4) -0.176(2) 0.3616(9) 0.055(6) Uani 1 1 d . . . C4 C -0.658(4) -0.145(2) 0.3140(9) 0.054(6) Uani 1 1 d . . . C5 C -0.516(4) -0.048(3) 0.2902(9) 0.064(7) Uani 1 1 d . . . C6 C -0.348(4) 0.017(2) 0.3134(8) 0.055(6) Uani 1 1 d . . . C7 C -0.304(4) -0.015(2) 0.3628(8) 0.047(5) Uani 1 1 d . . . C8 C -0.141(3) 0.0348(19) 0.3975(8) 0.038(5) Uani 1 1 d . . . C9 C 0.165(4) 0.1791(19) 0.4189(7) 0.044(5) Uani 1 1 d . . . C10 C 0.341(4) 0.286(2) 0.4082(9) 0.049(6) Uani 1 1 d . . . C11 C 0.379(4) 0.360(2) 0.3674(8) 0.051(6) Uani 1 1 d . . . C12 C 0.556(4) 0.460(2) 0.3679(10) 0.060(7) Uani 1 1 d . . . C13 C 0.686(4) 0.471(2) 0.4111(9) 0.054(6) Uani 1 1 d . . . C14 C 0.641(4) 0.399(2) 0.4514(8) 0.044(5) Uani 1 1 d . . . C15 C 0.466(4) 0.3044(19) 0.4507(8) 0.045(6) Uani 1 1 d . . . C16 C 0.367(4) 0.2090(18) 0.4870(8) 0.040(5) Uani 1 1 d . . . Cu2 Cu 0.5000 0.5000 0.0000 0.0424(11) Uani 1 2 d S . . F9 F 1.256(2) 0.9197(12) 0.0157(5) 0.063(3) Uani 1 1 d . . . F10 F 1.293(2) 1.0353(11) 0.0987(5) 0.069(4) Uani 1 1 d . . . F11 F 1.014(2) 0.9684(13) 0.1765(5) 0.072(4) Uani 1 1 d . . . F12 F 0.663(2) 0.7821(13) 0.1775(5) 0.069(4) Uani 1 1 d . . . F13 F 0.157(2) 0.5455(12) 0.2084(4) 0.068(3) Uani 1 1 d . . . F14 F -0.216(2) 0.3983(15) 0.2509(5) 0.081(4) Uani 1 1 d . . . F15 F -0.457(2) 0.2280(12) 0.2024(5) 0.068(4) Uani 1 1 d . . . F16 F -0.310(2) 0.1897(11) 0.1101(4) 0.058(3) Uani 1 1 d . . . N5 N 0.663(3) 0.6279(15) 0.0343(6) 0.045(4) Uani 1 1 d . . . N6 N 0.449(3) 0.5972(16) 0.1138(6) 0.043(4) Uani 1 1 d . . . N7 N 0.296(3) 0.4507(15) 0.0585(6) 0.041(4) Uani 1 1 d . . . N8 N 0.041(3) 0.2821(16) 0.0286(6) 0.045(4) Uani 1 1 d . . . C17 C 0.850(4) 0.712(2) 0.0152(8) 0.055(6) Uani 1 1 d . . . C18 C 0.923(4) 0.7870(18) 0.0523(8) 0.045(5) Uani 1 1 d . . . C19 C 1.102(4) 0.883(2) 0.0539(8) 0.049(6) Uani 1 1 d . . . C20 C 1.131(4) 0.941(2) 0.0957(9) 0.056(6) Uani 1 1 d . . . C21 C 0.974(4) 0.903(2) 0.1376(8) 0.056(6) Uani 1 1 d . . . C22 C 0.801(4) 0.814(2) 0.1369(9) 0.053(6) Uani 1 1 d . . . C23 C 0.780(4) 0.758(2) 0.0947(8) 0.049(5) Uani 1 1 d . . . C24 C 0.610(4) 0.651(2) 0.0823(8) 0.049(6) Uani 1 1 d . . . C25 C 0.302(4) 0.503(2) 0.1009(7) 0.048(6) Uani 1 1 d . . . C26 C 0.116(4) 0.442(2) 0.1350(8) 0.047(5) Uani 1 1 d . . . C27 C 0.041(4) 0.458(2) 0.1832(8) 0.051(6) Uani 1 1 d . . . C28 C -0.150(4) 0.387(3) 0.2050(8) 0.059(6) Uani 1 1 d . . . C29 C -0.257(4) 0.292(2) 0.1808(9) 0.056(6) Uani 1 1 d . . . C30 C -0.193(4) 0.2815(19) 0.1330(8) 0.044(5) Uani 1 1 d . . . C31 C 0.001(4) 0.3530(19) 0.1103(8) 0.047(5) Uani 1 1 d . . . C32 C 0.111(3) 0.3561(17) 0.0614(7) 0.035(5) 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 0.0236(17) 0.038(2) 0.060(2) 0.0048(18) 0.0008(15) -0.0032(14) F1 0.035(6) 0.065(8) 0.070(8) 0.011(7) 0.000(5) -0.014(6) F2 0.052(7) 0.065(8) 0.082(9) -0.007(7) -0.016(6) -0.017(6) F3 0.063(8) 0.086(10) 0.068(9) -0.003(8) -0.012(7) -0.015(7) F4 0.066(8) 0.061(8) 0.066(8) 0.016(7) -0.012(6) -0.019(7) F5 0.050(7) 0.059(8) 0.062(8) 0.012(7) -0.002(6) -0.008(6) F6 0.066(8) 0.055(8) 0.078(9) 0.010(8) 0.015(7) -0.015(6) F7 0.042(6) 0.039(7) 0.101(10) 0.000(7) 0.013(6) -0.013(6) F8 0.035(6) 0.036(6) 0.092(9) 0.005(6) 0.006(6) -0.012(5) N1 0.023(9) 0.052(11) 0.074(13) -0.004(11) 0.020(8) -0.009(8) N2 0.030(9) 0.042(11) 0.058(11) 0.003(9) 0.006(8) 0.010(8) N3 0.008(7) 0.034(9) 0.084(14) 0.001(10) -0.008(8) 0.000(7) N4 0.026(8) 0.024(9) 0.062(12) -0.002(9) 0.002(9) 0.002(7) C1 0.022(10) 0.058(14) 0.055(15) 0.003(13) 0.002(10) 0.003(10) C2 0.018(10) 0.058(14) 0.079(17) -0.007(14) -0.010(11) 0.001(11) C3 0.026(11) 0.061(15) 0.075(18) -0.017(14) -0.009(11) 0.009(11) C4 0.019(11) 0.065(16) 0.082(19) -0.014(15) -0.003(12) -0.010(11) C5 0.028(12) 0.098(19) 0.067(17) -0.014(16) -0.015(11) 0.003(13) C6 0.058(14) 0.043(14) 0.059(16) 0.005(13) 0.005(13) 0.001(12) C7 0.023(10) 0.044(13) 0.071(17) 0.006(13) -0.005(11) 0.000(10) C8 0.016(9) 0.035(12) 0.060(15) 0.007(12) 0.007(9) -0.002(9) C9 0.031(11) 0.039(13) 0.050(14) 0.008(12) -0.003(10) 0.009(10) C10 0.036(11) 0.037(12) 0.074(17) -0.007(14) 0.020(11) -0.011(10) C11 0.047(13) 0.060(15) 0.039(13) 0.016(13) 0.023(11) 0.002(11) C12 0.025(11) 0.064(16) 0.09(2) -0.011(16) 0.015(12) -0.014(11) C13 0.043(13) 0.064(16) 0.056(16) 0.000(14) 0.003(11) -0.012(11) C14 0.028(11) 0.048(13) 0.058(15) -0.012(13) -0.016(10) -0.006(10) C15 0.019(10) 0.041(13) 0.072(15) -0.012(12) -0.004(10) 0.011(10) C16 0.033(11) 0.025(11) 0.060(15) 0.009(11) 0.013(11) 0.000(9) Cu2 0.0210(17) 0.044(2) 0.061(2) 0.0010(18) -0.0045(15) -0.0008(14) F9 0.034(6) 0.070(8) 0.086(9) 0.002(8) -0.009(6) -0.013(6) F10 0.043(7) 0.047(7) 0.121(11) -0.009(7) -0.018(6) -0.018(6) F11 0.063(8) 0.076(9) 0.078(9) -0.014(8) -0.026(7) -0.003(7) F12 0.047(7) 0.092(10) 0.069(8) -0.011(8) -0.002(7) -0.012(7) F13 0.061(8) 0.071(9) 0.072(8) -0.012(7) -0.005(6) -0.010(7) F14 0.056(8) 0.119(12) 0.068(9) -0.001(9) 0.019(7) -0.019(7) F15 0.043(7) 0.072(9) 0.086(9) 0.021(8) 0.013(6) -0.010(6) F16 0.052(7) 0.045(7) 0.074(8) 0.018(7) 0.011(6) -0.013(6) N5 0.019(8) 0.045(10) 0.069(13) 0.005(10) -0.001(8) 0.002(7) N6 0.031(9) 0.045(10) 0.050(10) 0.010(9) -0.006(8) 0.000(8) N7 0.019(8) 0.037(9) 0.067(12) 0.008(9) -0.008(7) 0.000(7) N8 0.030(9) 0.048(11) 0.057(12) -0.024(10) -0.009(9) 0.002(8) C17 0.013(10) 0.092(18) 0.057(15) -0.025(14) -0.007(10) 0.005(11) C18 0.023(10) 0.031(12) 0.077(17) 0.013(12) -0.010(11) 0.011(9) C19 0.021(10) 0.043(13) 0.077(17) 0.017(13) -0.004(11) 0.003(10) C20 0.043(13) 0.033(13) 0.093(19) 0.002(14) -0.035(13) 0.002(11) C21 0.040(13) 0.046(14) 0.071(17) -0.004(14) -0.017(12) 0.028(12) C22 0.024(11) 0.049(14) 0.09(2) -0.017(14) -0.022(12) -0.010(10) C23 0.041(12) 0.040(12) 0.067(16) -0.001(13) -0.017(12) -0.008(10) C24 0.018(10) 0.056(14) 0.065(16) -0.008(13) -0.008(10) 0.009(10) C25 0.027(11) 0.057(14) 0.055(15) -0.003(13) -0.020(10) 0.017(11) C26 0.026(11) 0.050(14) 0.062(15) 0.002(12) -0.006(10) 0.004(10) C27 0.049(13) 0.038(13) 0.059(15) 0.001(12) 0.005(11) 0.012(11) C28 0.019(11) 0.097(19) 0.060(16) 0.019(15) 0.000(10) -0.015(12) C29 0.042(13) 0.042(13) 0.080(18) 0.010(13) 0.007(12) 0.001(11) C30 0.027(11) 0.041(13) 0.063(15) -0.004(12) 0.005(10) -0.004(10) C31 0.029(11) 0.040(12) 0.068(16) -0.005(12) -0.012(11) 0.004(10) C32 0.022(10) 0.019(10) 0.058(14) 0.023(11) -0.004(9) 0.002(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 N1 1.936(18) . ? Cu1 N1 1.936(18) 2_556 ? Cu1 N3 1.976(16) . ? Cu1 N3 1.976(16) 2_556 ? F1 C3 1.37(3) . ? F2 C4 1.32(2) . ? F3 C5 1.34(2) . ? F4 C6 1.35(2) . ? F5 C11 1.35(2) . ? F6 C12 1.30(3) . ? F7 C13 1.34(2) . ? F8 C14 1.33(2) . ? N1 C8 1.34(2) . ? N1 C1 1.43(3) . ? N2 C9 1.34(2) . ? N2 C8 1.35(2) . ? N3 C16 1.36(2) . ? N3 C9 1.36(2) . ? N4 C1 1.27(2) 2_556 ? N4 C16 1.33(2) . ? C1 N4 1.27(2) 2_556 ? C1 C2 1.49(3) . ? C2 C7 1.34(3) . ? C2 C3 1.37(3) . ? C3 C4 1.37(3) . ? C4 C5 1.41(3) . ? C5 C6 1.33(3) . ? C6 C7 1.42(3) . ? C7 C8 1.43(3) . ? C9 C10 1.48(3) . ? C10 C11 1.35(3) . ? C10 C15 1.39(3) . ? C11 C12 1.43(3) . ? C12 C13 1.40(3) . ? C13 C14 1.34(3) . ? C14 C15 1.37(3) . ? C15 C16 1.48(3) . ? Cu2 N5 1.940(16) 2_665 ? Cu2 N5 1.940(16) . ? Cu2 N7 1.955(16) 2_665 ? Cu2 N7 1.955(16) . ? F9 C19 1.34(2) . ? F10 C20 1.34(2) . ? F11 C21 1.35(2) . ? F12 C22 1.34(3) . ? F13 C27 1.36(2) . ? F14 C28 1.32(2) . ? F15 C29 1.35(2) . ? F16 C30 1.37(2) . ? N5 C24 1.39(3) . ? N5 C17 1.41(3) . ? N6 C24 1.30(3) . ? N6 C25 1.35(3) . ? N7 C25 1.33(2) . ? N7 C32 1.40(2) . ? N8 C32 1.31(2) . ? N8 C17 1.32(3) 2_665 ? C17 N8 1.32(3) 2_665 ? C17 C18 1.41(3) . ? C18 C23 1.39(3) . ? C18 C19 1.40(3) . ? C19 C20 1.37(3) . ? C20 C21 1.43(3) . ? C21 C22 1.32(3) . ? C22 C23 1.36(3) . ? C23 C24 1.52(3) . ? C25 C26 1.45(3) . ? C26 C31 1.37(3) . ? C26 C27 1.40(3) . ? C27 C28 1.36(3) . ? C28 C29 1.38(3) . ? C29 C30 1.37(3) . ? C30 C31 1.38(3) . ? C31 C32 1.45(3) . ? 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 Cu1 N1 180.0(8) . 2_556 ? N1 Cu1 N3 89.2(7) . . ? N1 Cu1 N3 90.8(7) 2_556 . ? N1 Cu1 N3 90.8(7) . 2_556 ? N1 Cu1 N3 89.2(7) 2_556 2_556 ? N3 Cu1 N3 180.0(9) . 2_556 ? C8 N1 C1 108.6(17) . . ? C8 N1 Cu1 128.0(13) . . ? C1 N1 Cu1 123.4(15) . . ? C9 N2 C8 121.8(17) . . ? C16 N3 C9 109.8(17) . . ? C16 N3 Cu1 124.3(14) . . ? C9 N3 Cu1 125.9(13) . . ? C1 N4 C16 120.9(17) 2_556 . ? N4 C1 N1 130.5(19) 2_556 . ? N4 C1 C2 124.9(19) 2_556 . ? N1 C1 C2 104(2) . . ? C7 C2 C3 122(2) . . ? C7 C2 C1 108.7(18) . . ? C3 C2 C1 129(2) . . ? F1 C3 C4 116.5(18) . . ? F1 C3 C2 124(2) . . ? C4 C3 C2 119(2) . . ? F2 C4 C3 123(2) . . ? F2 C4 C5 118(2) . . ? C3 C4 C5 119(2) . . ? C6 C5 F3 120(2) . . ? C6 C5 C4 121(2) . . ? F3 C5 C4 118.7(19) . . ? C5 C6 F4 121(2) . . ? C5 C6 C7 119(2) . . ? F4 C6 C7 119.4(19) . . ? C2 C7 C6 119(2) . . ? C2 C7 C8 107.6(19) . . ? C6 C7 C8 133(2) . . ? N1 C8 N2 127.3(18) . . ? N1 C8 C7 110.6(17) . . ? N2 C8 C7 122(2) . . ? N2 C9 N3 127.9(19) . . ? N2 C9 C10 123.7(18) . . ? N3 C9 C10 108.4(18) . . ? C11 C10 C15 122(2) . . ? C11 C10 C9 131(2) . . ? C15 C10 C9 106.5(19) . . ? C10 C11 F5 124(2) . . ? C10 C11 C12 119(2) . . ? F5 C11 C12 117(2) . . ? F6 C12 C13 122(2) . . ? F6 C12 C11 122(2) . . ? C13 C12 C11 116(2) . . ? F7 C13 C14 121.2(19) . . ? F7 C13 C12 115(2) . . ? C14 C13 C12 124(2) . . ? F8 C14 C13 120.1(18) . . ? F8 C14 C15 121(2) . . ? C13 C14 C15 119.2(19) . . ? C14 C15 C10 119(2) . . ? C14 C15 C16 134(2) . . ? C10 C15 C16 106.3(18) . . ? N4 C16 N3 130.0(19) . . ? N4 C16 C15 121.1(19) . . ? N3 C16 C15 109.0(18) . . ? N5 Cu2 N5 180.0(7) 2_665 . ? N5 Cu2 N7 89.7(7) 2_665 2_665 ? N5 Cu2 N7 90.3(7) . 2_665 ? N5 Cu2 N7 90.3(7) 2_665 . ? N5 Cu2 N7 89.7(7) . . ? N7 Cu2 N7 179.998(3) 2_665 . ? C24 N5 C17 109.0(17) . . ? C24 N5 Cu2 124.6(14) . . ? C17 N5 Cu2 126.4(14) . . ? C24 N6 C25 119.6(18) . . ? C25 N7 C32 109.6(17) . . ? C25 N7 Cu2 126.3(14) . . ? C32 N7 Cu2 124.1(13) . . ? C32 N8 C17 121.2(18) . 2_665 ? N8 C17 N5 127.7(19) 2_665 . ? N8 C17 C18 124(2) 2_665 . ? N5 C17 C18 108.4(18) . . ? C23 C18 C19 116(2) . . ? C23 C18 C17 110.6(18) . . ? C19 C18 C17 133(2) . . ? F9 C19 C20 117.2(19) . . ? F9 C19 C18 123(2) . . ? C20 C19 C18 120(2) . . ? F10 C20 C19 122(2) . . ? F10 C20 C21 119(2) . . ? C19 C20 C21 119(2) . . ? C22 C21 F11 124(2) . . ? C22 C21 C20 122(2) . . ? F11 C21 C20 114(2) . . ? C21 C22 F12 119(2) . . ? C21 C22 C23 117(2) . . ? F12 C22 C23 123.9(19) . . ? C22 C23 C18 125(2) . . ? C22 C23 C24 130(2) . . ? C18 C23 C24 104.5(18) . . ? N6 C24 N5 130.5(19) . . ? N6 C24 C23 122.1(19) . . ? N5 C24 C23 107(2) . . ? N7 C25 N6 129(2) . . ? N7 C25 C26 109.6(18) . . ? N6 C25 C26 121.3(19) . . ? C31 C26 C27 120(2) . . ? C31 C26 C25 105.9(18) . . ? C27 C26 C25 134(2) . . ? C28 C27 F13 119.9(19) . . ? C28 C27 C26 120(2) . . ? F13 C27 C26 120.3(19) . . ? F14 C28 C27 120(2) . . ? F14 C28 C29 119(2) . . ? C27 C28 C29 121(2) . . ? F15 C29 C30 121(2) . . ? F15 C29 C28 119(2) . . ? C30 C29 C28 119(2) . . ? F16 C30 C29 117.3(19) . . ? F16 C30 C31 121.8(18) . . ? C29 C30 C31 120.7(19) . . ? C26 C31 C30 120(2) . . ? C26 C31 C32 109.0(19) . . ? C30 C31 C32 131.4(18) . . ? N8 C32 N7 130.3(18) . . ? N8 C32 C31 123.8(17) . . ? N7 C32 C31 106.0(17) . . ? 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 N1 Cu1 N1 C8 -164(13) 2_556 . . . ? N3 Cu1 N1 C8 0.3(15) . . . . ? N3 Cu1 N1 C8 -179.7(15) 2_556 . . . ? N1 Cu1 N1 C1 15(14) 2_556 . . . ? N3 Cu1 N1 C1 179.1(13) . . . . ? N3 Cu1 N1 C1 -0.9(13) 2_556 . . . ? N1 Cu1 N3 C16 -179.5(13) . . . . ? N1 Cu1 N3 C16 0.5(13) 2_556 . . . ? N3 Cu1 N3 C16 150(28) 2_556 . . . ? N1 Cu1 N3 C9 1.0(13) . . . . ? N1 Cu1 N3 C9 -179.0(13) 2_556 . . . ? N3 Cu1 N3 C9 -29(28) 2_556 . . . ? C8 N1 C1 N4 -177.1(18) . . . 2_556 ? Cu1 N1 C1 N4 4(3) . . . 2_556 ? C8 N1 C1 C2 -2.2(18) . . . . ? Cu1 N1 C1 C2 178.8(11) . . . . ? N4 C1 C2 C7 178.0(17) 2_556 . . . ? N1 C1 C2 C7 2.7(19) . . . . ? N4 C1 C2 C3 -5(3) 2_556 . . . ? N1 C1 C2 C3 179.8(18) . . . . ? C7 C2 C3 F1 -179.8(16) . . . . ? C1 C2 C3 F1 4(3) . . . . ? C7 C2 C3 C4 -2(3) . . . . ? C1 C2 C3 C4 -178.9(18) . . . . ? F1 C3 C4 F2 -2(3) . . . . ? C2 C3 C4 F2 -179.6(16) . . . . ? F1 C3 C4 C5 -179.9(16) . . . . ? C2 C3 C4 C5 2(3) . . . . ? F2 C4 C5 C6 179.6(18) . . . . ? C3 C4 C5 C6 -2(3) . . . . ? F2 C4 C5 F3 3(3) . . . . ? C3 C4 C5 F3 -179.2(17) . . . . ? F3 C5 C6 F4 -3(3) . . . . ? C4 C5 C6 F4 179.9(17) . . . . ? F3 C5 C6 C7 178.7(17) . . . . ? C4 C5 C6 C7 2(3) . . . . ? C3 C2 C7 C6 2(3) . . . . ? C1 C2 C7 C6 179.1(16) . . . . ? C3 C2 C7 C8 -179.4(16) . . . . ? C1 C2 C7 C8 -2(2) . . . . ? C5 C6 C7 C2 -2(3) . . . . ? F4 C6 C7 C2 -179.7(16) . . . . ? C5 C6 C7 C8 -179.9(19) . . . . ? F4 C6 C7 C8 2(3) . . . . ? C1 N1 C8 N2 -179.5(16) . . . . ? Cu1 N1 C8 N2 -1(3) . . . . ? C1 N1 C8 C7 1.0(19) . . . . ? Cu1 N1 C8 C7 180.0(12) . . . . ? C9 N2 C8 N1 0(3) . . . . ? C9 N2 C8 C7 179.0(15) . . . . ? C2 C7 C8 N1 1(2) . . . . ? C6 C7 C8 N1 179.3(19) . . . . ? C2 C7 C8 N2 -178.7(15) . . . . ? C6 C7 C8 N2 0(3) . . . . ? C8 N2 C9 N3 2(2) . . . . ? C8 N2 C9 C10 179.9(15) . . . . ? C16 N3 C9 N2 178.2(16) . . . . ? Cu1 N3 C9 N2 -2(2) . . . . ? C16 N3 C9 C10 0.0(18) . . . . ? Cu1 N3 C9 C10 179.6(10) . . . . ? N2 C9 C10 C11 4(3) . . . . ? N3 C9 C10 C11 -177.4(18) . . . . ? N2 C9 C10 C15 -178.6(15) . . . . ? N3 C9 C10 C15 -0.2(18) . . . . ? C15 C10 C11 F5 179.7(16) . . . . ? C9 C10 C11 F5 -3(3) . . . . ? C15 C10 C11 C12 1(3) . . . . ? C9 C10 C11 C12 177.7(17) . . . . ? C10 C11 C12 F6 177.3(17) . . . . ? F5 C11 C12 F6 -2(3) . . . . ? C10 C11 C12 C13 2(3) . . . . ? F5 C11 C12 C13 -177.0(17) . . . . ? F6 C12 C13 F7 3(3) . . . . ? C11 C12 C13 F7 178.3(16) . . . . ? F6 C12 C13 C14 -179.2(18) . . . . ? C11 C12 C13 C14 -4(3) . . . . ? F7 C13 C14 F8 -2(3) . . . . ? C12 C13 C14 F8 179.8(18) . . . . ? F7 C13 C14 C15 -179.5(16) . . . . ? C12 C13 C14 C15 2(3) . . . . ? F8 C14 C15 C10 -176.8(15) . . . . ? C13 C14 C15 C10 1(3) . . . . ? F8 C14 C15 C16 3(3) . . . . ? C13 C14 C15 C16 -179.5(18) . . . . ? C11 C10 C15 C14 -2(3) . . . . ? C9 C10 C15 C14 -179.7(15) . . . . ? C11 C10 C15 C16 177.8(16) . . . . ? C9 C10 C15 C16 0.4(18) . . . . ? C1 N4 C16 N3 -3(3) 2_556 . . . ? C1 N4 C16 C15 176.7(15) 2_556 . . . ? C9 N3 C16 N4 -180.0(16) . . . . ? Cu1 N3 C16 N4 0(2) . . . . ? C9 N3 C16 C15 0.2(18) . . . . ? Cu1 N3 C16 C15 -179.4(10) . . . . ? C14 C15 C16 N4 0(3) . . . . ? C10 C15 C16 N4 179.8(15) . . . . ? C14 C15 C16 N3 179.7(18) . . . . ? C10 C15 C16 N3 -0.4(18) . . . . ? N5 Cu2 N5 C24 138(16) 2_665 . . . ? N7 Cu2 N5 C24 -179.9(14) 2_665 . . . ? N7 Cu2 N5 C24 0.1(14) . . . . ? N5 Cu2 N5 C17 -42(16) 2_665 . . . ? N7 Cu2 N5 C17 0.3(14) 2_665 . . . ? N7 Cu2 N5 C17 -179.7(14) . . . . ? N5 Cu2 N7 C25 -179.2(14) 2_665 . . . ? N5 Cu2 N7 C25 0.8(14) . . . . ? N7 Cu2 N7 C25 22(15) 2_665 . . . ? N5 Cu2 N7 C32 -1.4(12) 2_665 . . . ? N5 Cu2 N7 C32 178.5(12) . . . . ? N7 Cu2 N7 C32 -161(15) 2_665 . . . ? C24 N5 C17 N8 177.5(18) . . . 2_665 ? Cu2 N5 C17 N8 -3(3) . . . 2_665 ? C24 N5 C17 C18 1.8(19) . . . . ? Cu2 N5 C17 C18 -178.4(11) . . . . ? N8 C17 C18 C23 -178.3(18) 2_665 . . . ? N5 C17 C18 C23 -2(2) . . . . ? N8 C17 C18 C19 3(3) 2_665 . . . ? N5 C17 C18 C19 178.9(17) . . . . ? C23 C18 C19 F9 179.3(16) . . . . ? C17 C18 C19 F9 -2(3) . . . . ? C23 C18 C19 C20 1(2) . . . . ? C17 C18 C19 C20 179.2(18) . . . . ? F9 C19 C20 F10 3(3) . . . . ? C18 C19 C20 F10 -178.3(15) . . . . ? F9 C19 C20 C21 -179.2(15) . . . . ? C18 C19 C20 C21 0(3) . . . . ? F10 C20 C21 C22 177.7(17) . . . . ? C19 C20 C21 C22 0(3) . . . . ? F10 C20 C21 F11 -1(2) . . . . ? C19 C20 C21 F11 -179.0(15) . . . . ? F11 C21 C22 F12 -2(3) . . . . ? C20 C21 C22 F12 179.3(16) . . . . ? F11 C21 C22 C23 179.3(16) . . . . ? C20 C21 C22 C23 1(3) . . . . ? C21 C22 C23 C18 0(3) . . . . ? F12 C22 C23 C18 -179.0(17) . . . . ? C21 C22 C23 C24 178.2(18) . . . . ? F12 C22 C23 C24 0(3) . . . . ? C19 C18 C23 C22 0(3) . . . . ? C17 C18 C23 C22 -179.1(18) . . . . ? C19 C18 C23 C24 -179.1(15) . . . . ? C17 C18 C23 C24 2.0(19) . . . . ? C25 N6 C24 N5 0(3) . . . . ? C25 N6 C24 C23 179.9(15) . . . . ? C17 N5 C24 N6 179.2(18) . . . . ? Cu2 N5 C24 N6 -1(3) . . . . ? C17 N5 C24 C23 -0.6(19) . . . . ? Cu2 N5 C24 C23 179.6(11) . . . . ? C22 C23 C24 N6 0(3) . . . . ? C18 C23 C24 N6 179.3(16) . . . . ? C22 C23 C24 N5 -179.7(19) . . . . ? C18 C23 C24 N5 -0.8(19) . . . . ? C32 N7 C25 N6 -179.5(16) . . . . ? Cu2 N7 C25 N6 -1(3) . . . . ? C32 N7 C25 C26 0.4(18) . . . . ? Cu2 N7 C25 C26 178.4(11) . . . . ? C24 N6 C25 N7 1(3) . . . . ? C24 N6 C25 C26 -179.0(16) . . . . ? N7 C25 C26 C31 0(2) . . . . ? N6 C25 C26 C31 179.6(16) . . . . ? N7 C25 C26 C27 -179.9(19) . . . . ? N6 C25 C26 C27 0(3) . . . . ? C31 C26 C27 C28 -1(3) . . . . ? C25 C26 C27 C28 178.1(19) . . . . ? C31 C26 C27 F13 179.3(16) . . . . ? C25 C26 C27 F13 -1(3) . . . . ? F13 C27 C28 F14 -3(3) . . . . ? C26 C27 C28 F14 178.1(18) . . . . ? F13 C27 C28 C29 -176.4(17) . . . . ? C26 C27 C28 C29 4(3) . . . . ? F14 C28 C29 F15 10(3) . . . . ? C27 C28 C29 F15 -176.5(17) . . . . ? F14 C28 C29 C30 178.9(18) . . . . ? C27 C28 C29 C30 -7(3) . . . . ? F15 C29 C30 F16 -9(3) . . . . ? C28 C29 C30 F16 -178.1(17) . . . . ? F15 C29 C30 C31 176.5(16) . . . . ? C28 C29 C30 C31 7(3) . . . . ? C27 C26 C31 C30 2(3) . . . . ? C25 C26 C31 C30 -178.1(16) . . . . ? C27 C26 C31 C32 179.7(16) . . . . ? C25 C26 C31 C32 0.1(19) . . . . ? F16 C30 C31 C26 -178.9(16) . . . . ? C29 C30 C31 C26 -5(3) . . . . ? F16 C30 C31 C32 3(3) . . . . ? C29 C30 C31 C32 177.7(19) . . . . ? C17 N8 C32 N7 1(3) 2_665 . . . ? C17 N8 C32 C31 -179.1(16) 2_665 . . . ? C25 N7 C32 N8 179.5(16) . . . . ? Cu2 N7 C32 N8 1(2) . . . . ? C25 N7 C32 C31 -0.4(17) . . . . ? Cu2 N7 C32 C31 -178.4(11) . . . . ? C26 C31 C32 N8 -179.7(15) . . . . ? C30 C31 C32 N8 -2(3) . . . . ? C26 C31 C32 N7 0.2(18) . . . . ? C30 C31 C32 N7 178.1(18) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 29.36 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.345 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.155 # END