Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'C. Gibson' 'A. R. Kennedy' 'Colin L. McDavid' 'Kewin Roux-Duplatre' 'D. Sherrington' 'Graham Stones' 'Regis Tripoli' _publ_contact_author_name 'C. Gibson' _publ_contact_author_address ; Dept of Pure & Applied Chemistry University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UNITED KINGDOM ; _publ_contact_author_email C.L.GIBSON@STRATH.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Investigation of macrocyclisation routes to 1,4,7-triazacyclononanes: Efficient syntheses from 1,2-ditosylamides ; data_gib0406 _database_code_depnum_ccdc_archive 'CCDC 666004' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H27 Cu F6 N3 O4' _chemical_formula_weight 514.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' O O 0.0106 0.0060 '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' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 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' _cell_length_a 8.3666(2) _cell_length_b 15.4945(3) _cell_length_c 16.3029(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2113.45(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2768 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 1.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30600 _diffrn_reflns_av_R_equivalents 0.077 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4836 _reflns_number_gt 3771 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Denzo & Collect' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0186P)^2^+1.5838P] 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 -0.009(13) _refine_ls_number_reflns 4836 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.87709(4) 0.86730(2) 0.20338(2) 0.02015(9) Uani 1 1 d . . . F1 F 0.5432(3) 0.99203(14) 0.39498(13) 0.0514(6) Uani 1 1 d . . . F2 F 0.4699(2) 1.03073(14) 0.27428(14) 0.0472(6) Uani 1 1 d . . . F3 F 0.5927(3) 1.12063(11) 0.35315(12) 0.0445(5) Uani 1 1 d . . . F4 F 0.5648(3) 1.07045(14) 0.08160(17) 0.0797(10) Uani 1 1 d . . . F5 F 0.4021(3) 0.98475(16) 0.02636(17) 0.0765(8) Uani 1 1 d . . . F6 F 0.6294(4) 1.00675(19) -0.02580(14) 0.0893(10) Uani 1 1 d . . . O1 O 0.7561(2) 0.92568(12) 0.28936(14) 0.0242(5) Uani 1 1 d . . . O2 O 0.8394(3) 1.06175(13) 0.26792(14) 0.0346(6) Uani 1 1 d . . . O3 O 0.7612(3) 0.94017(13) 0.12383(13) 0.0274(5) Uani 1 1 d . . . O4 O 0.5556(3) 0.85267(16) 0.09375(16) 0.0474(7) Uani 1 1 d . . . N1 N 1.0038(3) 0.80217(16) 0.11685(16) 0.0250(6) Uani 1 1 d . . . N2 N 0.7981(3) 0.73939(15) 0.24465(14) 0.0183(6) Uani 1 1 d . . . N3 N 1.0709(3) 0.84150(15) 0.28090(15) 0.0227(6) Uani 1 1 d . . . C1 C 0.9658(4) 0.7075(2) 0.12249(19) 0.0260(8) Uani 1 1 d . . . H1A H 1.0527 0.6777 0.1524 0.031 Uiso 1 1 calc R . . H1B H 0.9606 0.6829 0.0665 0.031 Uiso 1 1 calc R . . C2 C 0.8076(4) 0.69100(19) 0.16629(19) 0.0248(7) Uani 1 1 d . . . H2A H 0.7182 0.7086 0.1302 0.030 Uiso 1 1 calc R . . H2B H 0.7966 0.6285 0.1775 0.030 Uiso 1 1 calc R . . C3 C 0.9141(4) 0.70751(18) 0.30744(18) 0.0214(7) Uani 1 1 d . . . H3 H 0.9954 0.6720 0.2778 0.026 Uiso 1 1 calc R . . C4 C 1.0041(4) 0.7840(2) 0.34715(19) 0.0231(7) Uani 1 1 d . . . H4 H 0.9247 0.8185 0.3792 0.028 Uiso 1 1 calc R . . C5 C 1.1989(4) 0.7998(2) 0.2306(2) 0.0310(8) Uani 1 1 d . . . H5A H 1.1967 0.7366 0.2390 0.037 Uiso 1 1 calc R . . H5B H 1.3049 0.8215 0.2480 0.037 Uiso 1 1 calc R . . C6 C 1.1722(4) 0.8202(2) 0.1403(2) 0.0315(9) Uani 1 1 d . . . H6A H 1.1969 0.8817 0.1299 0.038 Uiso 1 1 calc R . . H6B H 1.2451 0.7847 0.1064 0.038 Uiso 1 1 calc R . . C7 C 0.8409(4) 0.6498(2) 0.37361(18) 0.0292(8) Uani 1 1 d . . . H7A H 0.7593 0.6828 0.4044 0.035 Uiso 1 1 calc R . . H7B H 0.7873 0.6000 0.3474 0.035 Uiso 1 1 calc R . . C8 C 0.9688(4) 0.6173(2) 0.4329(2) 0.0385(9) Uani 1 1 d . . . H8A H 0.9182 0.5814 0.4759 0.046 Uiso 1 1 calc R . . H8B H 1.0463 0.5808 0.4028 0.046 Uiso 1 1 calc R . . C9 C 1.0557(5) 0.6922(2) 0.4723(2) 0.0386(9) Uani 1 1 d . . . H9A H 1.1403 0.6698 0.5091 0.046 Uiso 1 1 calc R . . H9B H 0.9797 0.7260 0.5059 0.046 Uiso 1 1 calc R . . C10 C 1.1308(5) 0.7508(2) 0.40732(19) 0.0355(8) Uani 1 1 d . . . H10A H 1.2136 0.7183 0.3768 0.043 Uiso 1 1 calc R . . H10B H 1.1833 0.8004 0.4345 0.043 Uiso 1 1 calc R . . C11 C 0.9768(4) 0.8323(2) 0.03188(18) 0.0337(9) Uani 1 1 d . . . H11A H 1.0489 0.8015 -0.0054 0.051 Uiso 1 1 calc R . . H11B H 0.9978 0.8944 0.0286 0.051 Uiso 1 1 calc R . . H11C H 0.8657 0.8208 0.0161 0.051 Uiso 1 1 calc R . . C12 C 0.6307(4) 0.74562(19) 0.27331(18) 0.0256(7) Uani 1 1 d . . . H12A H 0.5654 0.7732 0.2309 0.038 Uiso 1 1 calc R . . H12B H 0.6266 0.7801 0.3236 0.038 Uiso 1 1 calc R . . H12C H 0.5892 0.6876 0.2844 0.038 Uiso 1 1 calc R . . C13 C 1.1317(4) 0.92362(19) 0.3160(2) 0.0326(8) Uani 1 1 d . . . H13A H 1.2231 0.9116 0.3518 0.049 Uiso 1 1 calc R . . H13B H 1.0468 0.9515 0.3479 0.049 Uiso 1 1 calc R . . H13C H 1.1652 0.9620 0.2714 0.049 Uiso 1 1 calc R . . C14 C 0.7465(4) 1.00697(19) 0.2917(2) 0.0221(7) Uani 1 1 d . . . C15 C 0.5883(4) 1.0374(2) 0.3298(2) 0.0299(8) Uani 1 1 d . . . C16 C 0.6289(5) 0.9209(2) 0.09282(19) 0.0286(7) Uani 1 1 d . . . C17 C 0.5546(4) 0.9954(2) 0.0445(2) 0.0339(9) 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 0.02046(17) 0.01810(16) 0.02189(17) -0.00041(17) 0.00120(18) 0.00207(18) F1 0.0583(15) 0.0499(13) 0.0462(13) 0.0168(11) 0.0308(12) 0.0147(11) F2 0.0282(12) 0.0505(13) 0.0629(17) -0.0053(12) -0.0069(11) 0.0067(10) F3 0.0571(14) 0.0272(10) 0.0492(12) -0.0105(9) 0.0092(11) 0.0139(11) F4 0.103(2) 0.0338(13) 0.102(2) -0.0028(14) -0.0407(18) 0.0235(14) F5 0.0356(14) 0.0727(16) 0.121(2) 0.0376(16) -0.0291(16) 0.0022(13) F6 0.083(2) 0.132(2) 0.0529(15) 0.0541(16) 0.0163(17) 0.043(2) O1 0.0277(12) 0.0164(10) 0.0286(12) -0.0039(10) 0.0048(12) 0.0020(9) O2 0.0373(15) 0.0239(12) 0.0426(15) -0.0028(10) 0.0088(12) -0.0099(11) O3 0.0258(13) 0.0277(12) 0.0286(13) -0.0001(10) -0.0049(11) 0.0053(11) O4 0.0472(16) 0.0369(16) 0.0581(17) 0.0085(14) -0.0213(13) -0.0099(13) N1 0.0308(16) 0.0230(14) 0.0212(14) 0.0047(12) 0.0072(12) 0.0015(13) N2 0.0183(13) 0.0192(13) 0.0174(13) -0.0021(11) -0.0008(11) 0.0004(11) N3 0.0179(13) 0.0262(13) 0.0241(15) -0.0026(11) -0.0010(11) 0.0001(10) C1 0.038(2) 0.0211(16) 0.0193(17) -0.0027(14) 0.0001(15) 0.0093(15) C2 0.0346(19) 0.0167(15) 0.0230(16) -0.0015(14) -0.0035(15) 0.0002(14) C3 0.0244(17) 0.0206(14) 0.0192(16) 0.0012(13) 0.0005(14) 0.0050(13) C4 0.0213(17) 0.0271(17) 0.0209(17) 0.0009(14) -0.0008(14) 0.0032(14) C5 0.0177(17) 0.0372(19) 0.038(2) 0.0002(17) 0.0027(15) 0.0024(15) C6 0.026(2) 0.035(2) 0.0331(19) 0.0015(16) 0.0109(15) 0.0034(15) C7 0.035(2) 0.0267(18) 0.0264(17) 0.0050(14) 0.0021(14) -0.0009(15) C8 0.049(2) 0.040(2) 0.0271(18) 0.0130(17) -0.0003(17) 0.0112(19) C9 0.040(2) 0.052(2) 0.0234(18) 0.0071(18) -0.0080(17) 0.0104(19) C10 0.0302(19) 0.046(2) 0.0306(18) -0.0007(16) -0.0109(19) 0.007(2) C11 0.046(2) 0.0339(19) 0.0217(17) 0.0059(16) 0.0083(17) 0.0111(17) C12 0.0179(15) 0.0248(15) 0.0342(18) -0.0011(13) -0.0008(16) 0.0000(15) C13 0.0214(17) 0.0365(18) 0.040(2) -0.0009(15) -0.0081(18) -0.0031(17) C14 0.0232(16) 0.0231(16) 0.0199(16) -0.0010(16) -0.0011(16) -0.0030(14) C15 0.038(2) 0.0227(16) 0.0294(17) 0.0016(14) 0.0078(17) 0.0051(16) C16 0.0295(19) 0.0288(17) 0.0276(17) -0.0026(14) 0.0048(18) 0.0063(19) C17 0.030(2) 0.037(2) 0.034(2) 0.0045(17) 0.0012(17) 0.0032(17) _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 O1 1.951(2) . ? Cu1 O3 1.974(2) . ? Cu1 N1 2.033(3) . ? Cu1 N3 2.094(2) . ? Cu1 N2 2.195(2) . ? F1 C15 1.328(4) . ? F2 C15 1.346(4) . ? F3 C15 1.345(4) . ? F4 C17 1.313(4) . ? F5 C17 1.320(4) . ? F6 C17 1.318(4) . ? O1 C14 1.263(3) . ? O2 C14 1.215(3) . ? O3 C16 1.253(4) . ? O4 C16 1.222(4) . ? N1 C11 1.479(4) . ? N1 C6 1.487(4) . ? N1 C1 1.504(4) . ? N2 C12 1.480(4) . ? N2 C2 1.483(4) . ? N2 C3 1.494(4) . ? N3 C13 1.485(4) . ? N3 C5 1.496(4) . ? N3 C4 1.508(4) . ? C1 C2 1.525(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C7 1.529(4) . ? C3 C4 1.546(4) . ? C3 H3 1.0000 . ? C4 C10 1.533(4) . ? C4 H4 1.0000 . ? C5 C6 1.521(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.527(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.513(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.531(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.536(4) . ? C16 C17 1.530(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 O1 Cu1 O3 87.25(9) . . ? O1 Cu1 N1 177.64(10) . . ? O3 Cu1 N1 94.83(10) . . ? O1 Cu1 N3 93.25(10) . . ? O3 Cu1 N3 152.36(9) . . ? N1 Cu1 N3 85.42(10) . . ? O1 Cu1 N2 92.42(9) . . ? O3 Cu1 N2 124.75(9) . . ? N1 Cu1 N2 85.49(10) . . ? N3 Cu1 N2 82.87(9) . . ? C14 O1 Cu1 121.2(2) . . ? C16 O3 Cu1 124.2(2) . . ? C11 N1 C6 109.1(3) . . ? C11 N1 C1 109.4(3) . . ? C6 N1 C1 111.6(3) . . ? C11 N1 Cu1 114.4(2) . . ? C6 N1 Cu1 102.84(18) . . ? C1 N1 Cu1 109.36(19) . . ? C12 N2 C2 110.8(2) . . ? C12 N2 C3 114.8(2) . . ? C2 N2 C3 112.8(2) . . ? C12 N2 Cu1 108.84(18) . . ? C2 N2 Cu1 100.15(17) . . ? C3 N2 Cu1 108.23(17) . . ? C13 N3 C5 109.6(2) . . ? C13 N3 C4 111.0(2) . . ? C5 N3 C4 113.8(2) . . ? C13 N3 Cu1 109.52(18) . . ? C5 N3 Cu1 107.81(18) . . ? C4 N3 Cu1 104.98(18) . . ? N1 C1 C2 112.1(3) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? N2 C2 C1 111.4(3) . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? N2 C3 C7 114.6(2) . . ? N2 C3 C4 110.5(2) . . ? C7 C3 C4 110.3(2) . . ? N2 C3 H3 107.0 . . ? C7 C3 H3 107.0 . . ? C4 C3 H3 107.0 . . ? N3 C4 C10 113.6(3) . . ? N3 C4 C3 109.5(2) . . ? C10 C4 C3 110.4(2) . . ? N3 C4 H4 107.7 . . ? C10 C4 H4 107.7 . . ? C3 C4 H4 107.7 . . ? N3 C5 C6 109.6(3) . . ? N3 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? N3 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? N1 C6 C5 110.4(3) . . ? N1 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N1 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C3 111.0(3) . . ? C8 C7 H7A 109.4 . . ? C3 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C3 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C7 110.6(3) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 111.0(3) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C4 111.0(3) . . ? C9 C10 H10A 109.4 . . ? C4 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C4 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 O1 130.3(3) . . ? O2 C14 C15 117.8(3) . . ? O1 C14 C15 111.9(3) . . ? F1 C15 F3 106.8(3) . . ? F1 C15 F2 106.7(3) . . ? F3 C15 F2 106.5(3) . . ? F1 C15 C14 114.0(3) . . ? F3 C15 C14 112.6(3) . . ? F2 C15 C14 109.8(3) . . ? O4 C16 O3 130.1(3) . . ? O4 C16 C17 117.1(3) . . ? O3 C16 C17 112.8(3) . . ? F4 C17 F6 104.5(3) . . ? F4 C17 F5 106.1(3) . . ? F6 C17 F5 106.3(3) . . ? F4 C17 C16 113.9(3) . . ? F6 C17 C16 110.8(3) . . ? F5 C17 C16 114.5(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 O3 Cu1 O1 C14 -49.3(2) . . . . ? N1 Cu1 O1 C14 159(3) . . . . ? N3 Cu1 O1 C14 103.0(2) . . . . ? N2 Cu1 O1 C14 -174.0(2) . . . . ? O1 Cu1 O3 C16 -87.8(2) . . . . ? N1 Cu1 O3 C16 91.1(3) . . . . ? N3 Cu1 O3 C16 -179.6(2) . . . . ? N2 Cu1 O3 C16 3.2(3) . . . . ? O1 Cu1 N1 C11 155(3) . . . . ? O3 Cu1 N1 C11 3.4(2) . . . . ? N3 Cu1 N1 C11 -148.9(2) . . . . ? N2 Cu1 N1 C11 127.9(2) . . . . ? O1 Cu1 N1 C6 -86(3) . . . . ? O3 Cu1 N1 C6 121.54(19) . . . . ? N3 Cu1 N1 C6 -30.7(2) . . . . ? N2 Cu1 N1 C6 -113.9(2) . . . . ? O1 Cu1 N1 C1 32(3) . . . . ? O3 Cu1 N1 C1 -119.7(2) . . . . ? N3 Cu1 N1 C1 88.0(2) . . . . ? N2 Cu1 N1 C1 4.8(2) . . . . ? O1 Cu1 N2 C12 36.33(18) . . . . ? O3 Cu1 N2 C12 -52.0(2) . . . . ? N1 Cu1 N2 C12 -144.76(19) . . . . ? N3 Cu1 N2 C12 129.31(18) . . . . ? O1 Cu1 N2 C2 152.63(18) . . . . ? O3 Cu1 N2 C2 64.3(2) . . . . ? N1 Cu1 N2 C2 -28.45(18) . . . . ? N3 Cu1 N2 C2 -114.39(19) . . . . ? O1 Cu1 N2 C3 -89.08(18) . . . . ? O3 Cu1 N2 C3 -177.41(16) . . . . ? N1 Cu1 N2 C3 89.83(18) . . . . ? N3 Cu1 N2 C3 3.90(17) . . . . ? O1 Cu1 N3 C13 -56.8(2) . . . . ? O3 Cu1 N3 C13 33.5(3) . . . . ? N1 Cu1 N3 C13 125.1(2) . . . . ? N2 Cu1 N3 C13 -148.9(2) . . . . ? O1 Cu1 N3 C5 -176.04(19) . . . . ? O3 Cu1 N3 C5 -85.8(3) . . . . ? N1 Cu1 N3 C5 5.9(2) . . . . ? N2 Cu1 N3 C5 91.9(2) . . . . ? O1 Cu1 N3 C4 62.36(18) . . . . ? O3 Cu1 N3 C4 152.6(2) . . . . ? N1 Cu1 N3 C4 -115.69(18) . . . . ? N2 Cu1 N3 C4 -29.67(17) . . . . ? C11 N1 C1 C2 -105.5(3) . . . . ? C6 N1 C1 C2 133.7(3) . . . . ? Cu1 N1 C1 C2 20.5(3) . . . . ? C12 N2 C2 C1 162.2(2) . . . . ? C3 N2 C2 C1 -67.5(3) . . . . ? Cu1 N2 C2 C1 47.4(3) . . . . ? N1 C1 C2 N2 -49.0(3) . . . . ? C12 N2 C3 C7 26.5(3) . . . . ? C2 N2 C3 C7 -101.9(3) . . . . ? Cu1 N2 C3 C7 148.3(2) . . . . ? C12 N2 C3 C4 -98.9(3) . . . . ? C2 N2 C3 C4 132.7(2) . . . . ? Cu1 N2 C3 C4 22.9(3) . . . . ? C13 N3 C4 C10 -66.6(3) . . . . ? C5 N3 C4 C10 57.5(3) . . . . ? Cu1 N3 C4 C10 175.1(2) . . . . ? C13 N3 C4 C3 169.5(2) . . . . ? C5 N3 C4 C3 -66.4(3) . . . . ? Cu1 N3 C4 C3 51.3(2) . . . . ? N2 C3 C4 N3 -50.4(3) . . . . ? C7 C3 C4 N3 -178.2(2) . . . . ? N2 C3 C4 C10 -176.2(2) . . . . ? C7 C3 C4 C10 56.0(3) . . . . ? C13 N3 C5 C6 -98.5(3) . . . . ? C4 N3 C5 C6 136.6(3) . . . . ? Cu1 N3 C5 C6 20.6(3) . . . . ? C11 N1 C6 C5 173.3(3) . . . . ? C1 N1 C6 C5 -65.6(3) . . . . ? Cu1 N1 C6 C5 51.5(3) . . . . ? N3 C5 C6 N1 -49.5(4) . . . . ? N2 C3 C7 C8 177.6(2) . . . . ? C4 C3 C7 C8 -56.9(3) . . . . ? C3 C7 C8 C9 57.7(4) . . . . ? C7 C8 C9 C10 -57.3(4) . . . . ? C8 C9 C10 C4 57.0(4) . . . . ? N3 C4 C10 C9 -179.4(3) . . . . ? C3 C4 C10 C9 -56.0(3) . . . . ? Cu1 O1 C14 O2 -28.8(5) . . . . ? Cu1 O1 C14 C15 149.9(2) . . . . ? O2 C14 C15 F1 -139.9(3) . . . . ? O1 C14 C15 F1 41.3(4) . . . . ? O2 C14 C15 F3 -18.0(4) . . . . ? O1 C14 C15 F3 163.2(3) . . . . ? O2 C14 C15 F2 100.5(3) . . . . ? O1 C14 C15 F2 -78.3(4) . . . . ? Cu1 O3 C16 O4 -11.7(5) . . . . ? Cu1 O3 C16 C17 170.5(2) . . . . ? O4 C16 C17 F4 138.4(3) . . . . ? O3 C16 C17 F4 -43.6(4) . . . . ? O4 C16 C17 F6 -104.1(4) . . . . ? O3 C16 C17 F6 74.0(4) . . . . ? O4 C16 C17 F5 16.1(5) . . . . ? O3 C16 C17 F5 -165.8(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.331 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.071