# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'David Dolphin' _publ_contact_author_email DAVID.DOLPHIN@UBC.CA _publ_section_title ; Oxidized forms of tripyrrane: alpha-tripyrrinone, beta-tripyrrinone and a C2 symmetric hexapyrrole ; loop_ _publ_author_name 'D Dolphin' 'Brian O Patrick' 'Ji-Young Shin.' 'Zhan Zhang.' # Attachment 'tripyrrinone.cif' data_c2c _database_code_depnum_ccdc_archive 'CCDC 693823' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26.50 H10 Cl F10 N3 O' _chemical_formula_weight 611.83 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/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 29.240(10) _cell_length_b 23.151(9) _cell_length_c 7.016(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.060(10) _cell_angle_gamma 90.00 _cell_volume 4743(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2965 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 22.57 _exptl_crystal_description tablet _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.714 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2440 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.681 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13171 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1203 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.10 _reflns_number_total 13171 _reflns_number_gt 7238 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _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^)+(0.0479P)^2^+40.0184P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00087(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 13171 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1619 _refine_ls_R_factor_gt 0.0839 _refine_ls_wR_factor_ref 0.2458 _refine_ls_wR_factor_gt 0.2185 _refine_ls_goodness_of_fit_ref 1.204 _refine_ls_restrained_S_all 1.204 _refine_ls_shift/su_max 0.002 _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 C1 C 0.46227(18) 0.2652(3) 0.9185(8) 0.0334(15) Uani 1 1 d . . . C2 C 0.46603(18) 0.2073(3) 0.9934(9) 0.0434(16) Uani 1 1 d . . . H2 H 0.4807 0.1971 1.1128 0.052 Uiso 1 1 calc R . . C3 C 0.44591(17) 0.1702(2) 0.8709(8) 0.0341(14) Uani 1 1 d . . . H3 H 0.4437 0.1297 0.8893 0.041 Uiso 1 1 calc R . . C4 C 0.42797(16) 0.2015(2) 0.7055(8) 0.0279(13) Uani 1 1 d . . . C5 C 0.40643(16) 0.1811(2) 0.5453(7) 0.0245(13) Uani 1 1 d . . . C6 C 0.39006(17) 0.2159(2) 0.3865(8) 0.0283(14) Uani 1 1 d . . . C7 C 0.35972(17) 0.1982(2) 0.2318(7) 0.0306(14) Uani 1 1 d . . . H7 H 0.3485 0.1602 0.2079 0.037 Uiso 1 1 calc R . . C8 C 0.35002(17) 0.2453(2) 0.1267(8) 0.0308(14) Uani 1 1 d . . . H8 H 0.3300 0.2477 0.0159 0.037 Uiso 1 1 calc R . . C9 C 0.37616(17) 0.2918(2) 0.2160(7) 0.0264(13) Uani 1 1 d . . . C10 C 0.37763(16) 0.3486(2) 0.1637(7) 0.0240(13) Uani 1 1 d . . . C11 C 0.40813(17) 0.3902(2) 0.2389(7) 0.0244(13) Uani 1 1 d . . . C12 C 0.40655(18) 0.4503(2) 0.2279(8) 0.0336(15) Uani 1 1 d . . . H12 H 0.3842 0.4723 0.1567 0.040 Uiso 1 1 calc R . . C13 C 0.44266(18) 0.4721(2) 0.3372(7) 0.0340(14) Uani 1 1 d . . . H13 H 0.4497 0.5119 0.3535 0.041 Uiso 1 1 calc R . . C14 C 0.46737(18) 0.4266(2) 0.4206(8) 0.0369(15) Uani 1 1 d . . . H14 H 0.4941 0.4294 0.5032 0.044 Uiso 1 1 calc R . . C15 C 0.39734(17) 0.1177(2) 0.5377(7) 0.0239(13) Uani 1 1 d . . . C16 C 0.35754(19) 0.0942(2) 0.6035(7) 0.0303(14) Uani 1 1 d . . . C17 C 0.34975(18) 0.0363(2) 0.6032(8) 0.0308(14) Uani 1 1 d . . . C18 C 0.3819(2) -0.0004(3) 0.5391(8) 0.0374(15) Uani 1 1 d . . . C19 C 0.42137(19) 0.0209(2) 0.4706(8) 0.0297(14) Uani 1 1 d . . . C20 C 0.42870(19) 0.0790(2) 0.4685(8) 0.0310(14) Uani 1 1 d . . . C21 C 0.34309(16) 0.3703(2) 0.0182(7) 0.0228(13) Uani 1 1 d . . . C22 C 0.35455(17) 0.3909(2) -0.1578(8) 0.0291(14) Uani 1 1 d . . . C23 C 0.32353(19) 0.4144(2) -0.2898(7) 0.0301(14) Uani 1 1 d . . . C24 C 0.2777(2) 0.4152(2) -0.2462(9) 0.0410(16) Uani 1 1 d . . . C25 C 0.26509(18) 0.3949(2) -0.0759(9) 0.0371(15) Uani 1 1 d . . . C26 C 0.29686(18) 0.3726(2) 0.0527(8) 0.0330(15) Uani 1 1 d . . . C27 C 0.2620(5) 0.2305(8) 0.465(2) 0.087(5) Uani 0.50 1 d P . . H27A H 0.2704 0.1899 0.4937 0.104 Uiso 0.50 1 calc PR . . H27B H 0.2812 0.2440 0.3613 0.104 Uiso 0.50 1 calc PR . . N1 N 0.43847(15) 0.2590(2) 0.7434(7) 0.0296(12) Uani 1 1 d . . . N2 N 0.40061(14) 0.27128(18) 0.3773(6) 0.0273(11) Uani 1 1 d . . . N3 N 0.44598(16) 0.3776(2) 0.3612(6) 0.0301(12) Uani 1 1 d . . . F1 F 0.32596(10) 0.12885(13) 0.6728(5) 0.0447(9) Uani 1 1 d . . . F2 F 0.31135(10) 0.01517(13) 0.6748(5) 0.0503(10) Uani 1 1 d . . . F3 F 0.37534(11) -0.05746(13) 0.5420(5) 0.0493(9) Uani 1 1 d . . . F4 F 0.45299(10) -0.01548(12) 0.4068(5) 0.0485(10) Uani 1 1 d . . . F5 F 0.46761(10) 0.09913(13) 0.4004(5) 0.0452(9) Uani 1 1 d . . . F6 F 0.39843(10) 0.38988(13) -0.2052(4) 0.0404(9) Uani 1 1 d . . . F7 F 0.33537(11) 0.43352(14) -0.4598(4) 0.0523(10) Uani 1 1 d . . . F8 F 0.24653(11) 0.43564(15) -0.3760(5) 0.0575(11) Uani 1 1 d . . . F9 F 0.22039(10) 0.39614(15) -0.0337(5) 0.0589(11) Uani 1 1 d . . . F10 F 0.28315(10) 0.35517(14) 0.2225(5) 0.0493(10) Uani 1 1 d . . . Cl1 Cl 0.2038(7) 0.2333(3) 0.3839(9) 0.056(4) Uani 0.47(4) 1 d P . . Cl2 Cl 0.2734(10) 0.2714(5) 0.661(3) 0.118(5) Uani 0.53(4) 1 d P . . O1 O 0.47780(12) 0.31035(18) 0.9805(6) 0.0477(12) Uani 1 1 d . . . H3N H 0.4535(16) 0.342(2) 0.374(7) 0.028(17) Uiso 1 1 d . . . H1N H 0.4297(14) 0.2839(18) 0.668(6) 0.005(14) Uiso 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 C1 0.030(3) 0.043(4) 0.027(4) -0.012(3) 0.000(3) 0.001(3) C2 0.040(4) 0.045(4) 0.044(4) -0.002(4) -0.006(3) 0.013(3) C3 0.030(3) 0.035(4) 0.036(4) 0.003(3) -0.004(3) 0.001(3) C4 0.023(3) 0.030(4) 0.031(4) 0.003(3) 0.000(3) 0.001(3) C5 0.023(3) 0.030(3) 0.020(3) 0.000(3) 0.001(3) 0.002(3) C6 0.028(3) 0.028(4) 0.027(4) 0.002(3) -0.006(3) -0.004(3) C7 0.034(3) 0.030(4) 0.027(4) -0.005(3) 0.000(3) -0.002(3) C8 0.029(3) 0.034(4) 0.029(4) -0.001(3) -0.004(3) -0.006(3) C9 0.027(3) 0.026(3) 0.025(4) 0.005(3) -0.004(3) 0.001(3) C10 0.024(3) 0.028(3) 0.020(3) 0.006(3) 0.001(2) -0.001(3) C11 0.022(3) 0.030(4) 0.022(3) 0.004(3) 0.006(2) 0.003(3) C12 0.035(4) 0.024(4) 0.042(4) -0.001(3) 0.003(3) -0.001(3) C13 0.044(4) 0.024(3) 0.035(4) -0.007(3) 0.010(3) -0.008(3) C14 0.030(3) 0.038(4) 0.043(4) 0.000(3) 0.004(3) -0.010(3) C15 0.026(3) 0.022(3) 0.024(3) 0.005(2) -0.004(2) -0.007(2) C16 0.036(4) 0.035(4) 0.020(3) 0.001(3) -0.003(3) 0.007(3) C17 0.030(4) 0.025(4) 0.036(4) 0.011(3) -0.004(3) -0.013(3) C18 0.054(4) 0.016(3) 0.040(4) 0.013(3) -0.017(3) -0.007(3) C19 0.034(3) 0.020(3) 0.035(4) -0.003(3) -0.004(3) 0.003(3) C20 0.031(4) 0.028(4) 0.033(4) 0.000(3) -0.007(3) -0.004(3) C21 0.019(3) 0.024(3) 0.025(3) 0.001(3) -0.003(3) 0.002(2) C22 0.021(3) 0.036(4) 0.030(4) -0.002(3) -0.001(3) 0.005(3) C23 0.042(4) 0.038(4) 0.010(3) 0.003(3) 0.001(3) 0.014(3) C24 0.043(4) 0.042(4) 0.037(4) 0.008(3) -0.012(3) 0.016(3) C25 0.024(3) 0.045(4) 0.043(4) 0.004(3) 0.004(3) 0.010(3) C26 0.031(4) 0.046(4) 0.023(4) 0.009(3) 0.003(3) 0.003(3) C27 0.069(14) 0.124(18) 0.068(13) 0.000(11) 0.019(9) 0.025(10) N1 0.035(3) 0.024(3) 0.028(3) 0.001(2) -0.002(2) 0.002(2) N2 0.030(3) 0.028(3) 0.024(3) -0.002(2) -0.003(2) -0.003(2) N3 0.036(3) 0.026(3) 0.028(3) 0.001(2) -0.002(2) -0.002(3) F1 0.036(2) 0.038(2) 0.061(2) 0.0048(17) 0.0118(17) -0.0007(16) F2 0.048(2) 0.041(2) 0.061(3) 0.0153(17) -0.0002(18) -0.0187(16) F3 0.063(2) 0.027(2) 0.056(2) 0.0011(17) -0.0149(18) -0.0080(17) F4 0.050(2) 0.030(2) 0.064(3) -0.0098(17) -0.0057(18) 0.0120(16) F5 0.034(2) 0.037(2) 0.066(3) -0.0042(17) 0.0120(17) -0.0036(16) F6 0.034(2) 0.051(2) 0.036(2) 0.0077(16) 0.0090(15) 0.0016(16) F7 0.060(2) 0.073(3) 0.025(2) 0.0154(18) 0.0060(17) 0.0088(19) F8 0.049(2) 0.076(3) 0.046(2) 0.0048(19) -0.0141(18) 0.0218(19) F9 0.0218(19) 0.082(3) 0.073(3) 0.010(2) 0.0014(17) 0.0108(18) F10 0.036(2) 0.071(3) 0.041(2) 0.0162(19) 0.0103(17) -0.0003(17) Cl1 0.059(6) 0.059(3) 0.048(5) -0.015(2) -0.018(3) 0.010(3) Cl2 0.089(11) 0.100(5) 0.158(9) -0.025(6) -0.062(9) -0.015(5) O1 0.033(2) 0.048(3) 0.061(3) -0.017(2) -0.006(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.211(6) . ? C1 N1 1.386(7) . ? C1 C2 1.442(7) . ? C2 C3 1.329(7) . ? C2 H2 0.9500 . ? C3 C4 1.443(7) . ? C3 H3 0.9500 . ? C4 C5 1.345(7) . ? C4 N1 1.388(6) . ? C5 C6 1.436(7) . ? C5 C15 1.494(7) . ? C6 N2 1.321(6) . ? C6 C7 1.425(7) . ? C7 C8 1.339(7) . ? C7 H7 0.9500 . ? C8 C9 1.444(7) . ? C8 H8 0.9500 . ? C9 C10 1.366(6) . ? C9 N2 1.390(6) . ? C10 C11 1.397(7) . ? C10 C21 1.485(7) . ? C11 C12 1.394(7) . ? C11 N3 1.395(6) . ? C12 C13 1.368(7) . ? C12 H12 0.9500 . ? C13 C14 1.388(7) . ? C13 H13 0.9500 . ? C14 N3 1.350(6) . ? C14 H14 0.9500 . ? C15 C16 1.385(7) . ? C15 C20 1.388(7) . ? C16 F1 1.334(6) . ? C16 C17 1.360(7) . ? C17 F2 1.347(5) . ? C17 C18 1.361(7) . ? C18 F3 1.336(6) . ? C18 C19 1.365(7) . ? C19 F4 1.345(5) . ? C19 C20 1.362(7) . ? C20 F5 1.341(6) . ? C21 C22 1.382(7) . ? C21 C26 1.387(7) . ? C22 F6 1.343(5) . ? C22 C23 1.373(7) . ? C23 F7 1.335(6) . ? C23 C24 1.390(7) . ? C24 F8 1.341(6) . ? C24 C25 1.353(8) . ? C25 F9 1.356(6) . ? C25 C26 1.362(7) . ? C26 F10 1.339(6) . ? C27 Cl2 1.69(2) . ? C27 Cl1 1.77(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? N1 H1N 0.82(4) . ? N3 H3N 0.85(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 C1 N1 124.7(6) . . ? O1 C1 C2 130.6(6) . . ? N1 C1 C2 104.6(5) . . ? C3 C2 C1 110.0(5) . . ? C3 C2 H2 125.0 . . ? C1 C2 H2 125.0 . . ? C2 C3 C4 109.0(5) . . ? C2 C3 H3 125.5 . . ? C4 C3 H3 125.5 . . ? C5 C4 N1 125.9(5) . . ? C5 C4 C3 129.1(5) . . ? N1 C4 C3 105.1(5) . . ? C4 C5 C6 125.0(5) . . ? C4 C5 C15 116.7(4) . . ? C6 C5 C15 118.2(4) . . ? N2 C6 C7 112.3(4) . . ? N2 C6 C5 120.8(5) . . ? C7 C6 C5 126.7(5) . . ? C8 C7 C6 106.8(5) . . ? C8 C7 H7 126.6 . . ? C6 C7 H7 126.6 . . ? C7 C8 C9 106.1(5) . . ? C7 C8 H8 126.9 . . ? C9 C8 H8 126.9 . . ? C10 C9 N2 121.7(5) . . ? C10 C9 C8 128.7(5) . . ? N2 C9 C8 109.6(4) . . ? C9 C10 C11 126.2(5) . . ? C9 C10 C21 118.7(5) . . ? C11 C10 C21 115.0(4) . . ? C12 C11 N3 105.4(5) . . ? C12 C11 C10 130.5(5) . . ? N3 C11 C10 123.9(5) . . ? C13 C12 C11 108.3(5) . . ? C13 C12 H12 125.8 . . ? C11 C12 H12 125.8 . . ? C12 C13 C14 109.0(5) . . ? C12 C13 H13 125.5 . . ? C14 C13 H13 125.5 . . ? N3 C14 C13 106.5(5) . . ? N3 C14 H14 126.7 . . ? C13 C14 H14 126.7 . . ? C16 C15 C20 116.5(5) . . ? C16 C15 C5 121.6(5) . . ? C20 C15 C5 121.9(5) . . ? F1 C16 C17 118.3(5) . . ? F1 C16 C15 119.8(5) . . ? C17 C16 C15 121.9(5) . . ? F2 C17 C16 120.0(5) . . ? F2 C17 C18 120.1(5) . . ? C16 C17 C18 119.8(5) . . ? F3 C18 C17 120.6(5) . . ? F3 C18 C19 119.2(6) . . ? C17 C18 C19 120.2(6) . . ? F4 C19 C20 120.2(5) . . ? F4 C19 C18 120.0(5) . . ? C20 C19 C18 119.8(5) . . ? F5 C20 C19 119.0(5) . . ? F5 C20 C15 119.3(5) . . ? C19 C20 C15 121.7(5) . . ? C22 C21 C26 115.3(5) . . ? C22 C21 C10 122.9(5) . . ? C26 C21 C10 121.8(5) . . ? F6 C22 C23 116.5(5) . . ? F6 C22 C21 119.7(4) . . ? C23 C22 C21 123.8(5) . . ? F7 C23 C22 122.7(5) . . ? F7 C23 C24 119.4(5) . . ? C22 C23 C24 117.8(5) . . ? F8 C24 C25 121.0(6) . . ? F8 C24 C23 118.9(5) . . ? C25 C24 C23 120.1(5) . . ? C24 C25 F9 119.8(5) . . ? C24 C25 C26 120.5(5) . . ? F9 C25 C26 119.6(5) . . ? F10 C26 C25 118.5(5) . . ? F10 C26 C21 119.0(5) . . ? C25 C26 C21 122.4(5) . . ? Cl2 C27 Cl1 112.7(12) . . ? Cl2 C27 H27A 109.1 . . ? Cl1 C27 H27A 109.1 . . ? Cl2 C27 H27B 109.1 . . ? Cl1 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C1 N1 C4 111.4(5) . . ? C1 N1 H1N 129(3) . . ? C4 N1 H1N 120(3) . . ? C6 N2 C9 105.1(4) . . ? C14 N3 C11 110.7(5) . . ? C14 N3 H3N 131(3) . . ? C11 N3 H3N 117(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 O1 C1 C2 C3 -175.9(6) . . . . ? N1 C1 C2 C3 0.0(6) . . . . ? C1 C2 C3 C4 0.6(7) . . . . ? C2 C3 C4 C5 177.7(5) . . . . ? C2 C3 C4 N1 -1.0(6) . . . . ? N1 C4 C5 C6 -0.8(9) . . . . ? C3 C4 C5 C6 -179.4(5) . . . . ? N1 C4 C5 C15 -178.1(5) . . . . ? C3 C4 C5 C15 3.3(8) . . . . ? C4 C5 C6 N2 8.9(8) . . . . ? C15 C5 C6 N2 -173.8(5) . . . . ? C4 C5 C6 C7 -167.0(5) . . . . ? C15 C5 C6 C7 10.3(8) . . . . ? N2 C6 C7 C8 -2.2(6) . . . . ? C5 C6 C7 C8 174.0(5) . . . . ? C6 C7 C8 C9 1.9(6) . . . . ? C7 C8 C9 C10 -179.3(5) . . . . ? C7 C8 C9 N2 -1.2(6) . . . . ? N2 C9 C10 C11 11.6(8) . . . . ? C8 C9 C10 C11 -170.5(5) . . . . ? N2 C9 C10 C21 -166.2(5) . . . . ? C8 C9 C10 C21 11.7(8) . . . . ? C9 C10 C11 C12 -164.1(5) . . . . ? C21 C10 C11 C12 13.8(8) . . . . ? C9 C10 C11 N3 9.3(9) . . . . ? C21 C10 C11 N3 -172.8(5) . . . . ? N3 C11 C12 C13 1.0(6) . . . . ? C10 C11 C12 C13 175.4(5) . . . . ? C11 C12 C13 C14 -0.6(6) . . . . ? C12 C13 C14 N3 -0.1(6) . . . . ? C4 C5 C15 C16 89.1(6) . . . . ? C6 C5 C15 C16 -88.4(6) . . . . ? C4 C5 C15 C20 -89.5(6) . . . . ? C6 C5 C15 C20 93.0(6) . . . . ? C20 C15 C16 F1 179.7(4) . . . . ? C5 C15 C16 F1 1.1(7) . . . . ? C20 C15 C16 C17 0.9(8) . . . . ? C5 C15 C16 C17 -177.7(5) . . . . ? F1 C16 C17 F2 -1.2(7) . . . . ? C15 C16 C17 F2 177.6(5) . . . . ? F1 C16 C17 C18 -177.9(5) . . . . ? C15 C16 C17 C18 0.9(8) . . . . ? F2 C17 C18 F3 1.7(8) . . . . ? C16 C17 C18 F3 178.4(5) . . . . ? F2 C17 C18 C19 -178.5(5) . . . . ? C16 C17 C18 C19 -1.8(8) . . . . ? F3 C18 C19 F4 0.1(8) . . . . ? C17 C18 C19 F4 -179.8(5) . . . . ? F3 C18 C19 C20 -179.4(5) . . . . ? C17 C18 C19 C20 0.8(8) . . . . ? F4 C19 C20 F5 0.6(7) . . . . ? C18 C19 C20 F5 -179.9(5) . . . . ? F4 C19 C20 C15 -178.3(5) . . . . ? C18 C19 C20 C15 1.1(8) . . . . ? C16 C15 C20 F5 179.1(4) . . . . ? C5 C15 C20 F5 -2.3(7) . . . . ? C16 C15 C20 C19 -2.0(8) . . . . ? C5 C15 C20 C19 176.7(5) . . . . ? C9 C10 C21 C22 -116.1(6) . . . . ? C11 C10 C21 C22 65.8(7) . . . . ? C9 C10 C21 C26 65.6(7) . . . . ? C11 C10 C21 C26 -112.4(6) . . . . ? C26 C21 C22 F6 -179.2(4) . . . . ? C10 C21 C22 F6 2.4(7) . . . . ? C26 C21 C22 C23 2.4(8) . . . . ? C10 C21 C22 C23 -176.0(5) . . . . ? F6 C22 C23 F7 2.2(8) . . . . ? C21 C22 C23 F7 -179.4(5) . . . . ? F6 C22 C23 C24 178.9(5) . . . . ? C21 C22 C23 C24 -2.6(8) . . . . ? F7 C23 C24 F8 -0.4(8) . . . . ? C22 C23 C24 F8 -177.3(5) . . . . ? F7 C23 C24 C25 178.8(5) . . . . ? C22 C23 C24 C25 1.9(8) . . . . ? F8 C24 C25 F9 -1.2(9) . . . . ? C23 C24 C25 F9 179.6(5) . . . . ? F8 C24 C25 C26 178.0(5) . . . . ? C23 C24 C25 C26 -1.2(9) . . . . ? C24 C25 C26 F10 177.4(5) . . . . ? F9 C25 C26 F10 -3.5(8) . . . . ? C24 C25 C26 C21 1.1(9) . . . . ? F9 C25 C26 C21 -179.8(5) . . . . ? C22 C21 C26 F10 -177.8(5) . . . . ? C10 C21 C26 F10 0.5(8) . . . . ? C22 C21 C26 C25 -1.5(8) . . . . ? C10 C21 C26 C25 176.8(5) . . . . ? O1 C1 N1 C4 175.5(5) . . . . ? C2 C1 N1 C4 -0.7(6) . . . . ? C5 C4 N1 C1 -177.8(5) . . . . ? C3 C4 N1 C1 1.1(6) . . . . ? C7 C6 N2 C9 1.4(6) . . . . ? C5 C6 N2 C9 -175.1(5) . . . . ? C10 C9 N2 C6 178.1(5) . . . . ? C8 C9 N2 C6 -0.1(6) . . . . ? C13 C14 N3 C11 0.7(6) . . . . ? C12 C11 N3 C14 -1.1(6) . . . . ? C10 C11 N3 C14 -175.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.706 _refine_diff_density_min -0.642 _refine_diff_density_rms 0.146