# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1c _database_code_depnum_ccdc_archive 'CCDC 888803' #TrackingRef '- 1a-2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H20 Cl3 F8 I4 N4' _chemical_formula_weight 1322.55 _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' I I -0.4742 1.8119 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _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 20.9771(19) _cell_length_b 20.4699(18) _cell_length_c 10.1640(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.3160(10) _cell_angle_gamma 90.00 _cell_volume 4345.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6268 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.97 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.021 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2492 _exptl_absorpt_coefficient_mu 3.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3470 _exptl_absorpt_correction_T_max 0.6034 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15952 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4043 _reflns_number_gt 3295 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0589P)^2^+10.4719P] 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 4043 _refine_ls_number_parameters 276 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _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 Cl1 Cl 0.5000 0.4552(5) 0.7500 0.336(5) Uani 1 2 d SDU . . Cl2 Cl 0.4681(9) 0.5609(6) 0.8984(17) 0.337(7) Uani 0.50 1 d PDU . . Cl3 Cl 0.5586(5) 0.5788(5) 0.7254(13) 0.263(5) Uani 0.50 1 d PDU . . C20 C 0.5213(10) 0.5278(5) 0.813(2) 0.304(8) Uani 1 1 d DU . . H20A H 0.5544 0.5163 0.8803 0.364 Uiso 1 1 d R . . C1 C 0.2112(2) 1.0145(2) 0.1485(5) 0.0488(12) Uani 1 1 d . . . C2 C 0.1904(2) 0.9569(2) 0.0880(5) 0.0488(12) Uani 1 1 d . . . C3 C 0.2076(2) 0.8955(2) 0.1335(5) 0.0482(12) Uani 1 1 d . . . C4 C 0.2489(2) 0.8925(2) 0.2469(6) 0.0495(12) Uani 1 1 d . . . C5 C 0.2733(2) 0.9479(3) 0.3078(5) 0.0513(12) Uani 1 1 d . . . C6 C 0.2535(2) 1.0083(2) 0.2581(5) 0.0508(12) Uani 1 1 d . . . C7 C 0.3469(3) 0.7709(3) 0.5778(6) 0.0589(14) Uani 1 1 d . . . H7 H 0.3026 0.7667 0.5729 0.071 Uiso 1 1 calc R . . C8 C 0.3747(2) 0.8264(2) 0.6375(5) 0.0478(11) Uani 1 1 d . . . H8 H 0.3492 0.8586 0.6704 0.057 Uiso 1 1 calc R . . C9 C 0.4409(2) 0.8332(2) 0.6475(4) 0.0420(10) Uani 1 1 d . . . C10 C 0.4757(3) 0.7833(2) 0.5959(5) 0.0502(12) Uani 1 1 d . . . H10 H 0.5201 0.7856 0.6005 0.060 Uiso 1 1 calc R . . C11 C 0.4438(3) 0.7303(2) 0.5376(6) 0.0627(15) Uani 1 1 d . . . H11 H 0.4680 0.6973 0.5035 0.075 Uiso 1 1 calc R . . C12 C 0.4719(2) 0.8931(2) 0.7068(5) 0.0397(10) Uani 1 1 d . . . C13 C 0.4442(2) 0.9533(2) 0.6694(5) 0.0405(10) Uani 1 1 d . . . H13 H 0.4060 0.9533 0.6148 0.049 Uiso 1 1 calc R . . C14 C 0.4708(2) 1.0129(2) 0.7098(4) 0.0387(10) Uani 1 1 d . . . C15 C 0.3781(2) 1.1401(2) 0.5052(5) 0.0526(13) Uani 1 1 d . . . H15 H 0.3603 1.1447 0.4185 0.063 Uiso 1 1 calc R . . C16 C 0.4092(2) 1.0821(2) 0.5403(5) 0.0454(11) Uani 1 1 d . . . H16 H 0.4123 1.0491 0.4783 0.054 Uiso 1 1 calc R . . C17 C 0.4353(2) 1.0741(2) 0.6686(4) 0.0378(10) Uani 1 1 d . . . C18 C 0.4269(2) 1.1245(2) 0.7564(5) 0.0449(11) Uani 1 1 d . . . H18 H 0.4420 1.1203 0.8449 0.054 Uiso 1 1 calc R . . C19 C 0.3961(3) 1.1807(2) 0.7117(6) 0.0535(13) Uani 1 1 d . . . H19 H 0.3919 1.2144 0.7717 0.064 Uiso 1 1 calc R . . F1 F 0.15071(18) 0.96138(14) -0.0245(3) 0.0701(9) Uani 1 1 d . . . F2 F 0.26607(15) 0.83478(15) 0.3007(3) 0.0659(8) Uani 1 1 d . . . F3 F 0.31427(16) 0.94397(18) 0.4171(3) 0.0742(10) Uani 1 1 d . . . F4 F 0.27638(17) 1.06174(16) 0.3243(3) 0.0724(9) Uani 1 1 d . . . I1 I 0.175937(18) 1.105510(16) 0.08101(4) 0.05925(15) Uani 1 1 d . . . I2 I 0.173575(18) 0.810411(16) 0.03597(4) 0.05942(15) Uani 1 1 d . . . N1 N 0.3808(2) 0.7237(2) 0.5273(5) 0.0642(13) Uani 1 1 d . . . N2 N 0.3722(2) 1.18946(19) 0.5877(5) 0.0548(11) Uani 1 1 d . . . _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 Cl1 0.355(9) 0.298(8) 0.348(9) 0.000 -0.004(8) 0.000 Cl2 0.301(10) 0.403(11) 0.322(11) -0.019(8) 0.107(8) -0.018(8) Cl3 0.168(6) 0.335(9) 0.296(10) -0.050(8) 0.080(7) -0.053(7) C20 0.311(13) 0.310(11) 0.294(13) 0.007(8) 0.048(9) 0.000(9) C1 0.053(3) 0.031(2) 0.062(3) 0.002(2) 0.007(2) -0.004(2) C2 0.049(3) 0.038(3) 0.057(3) 0.001(2) -0.007(2) 0.003(2) C3 0.054(3) 0.031(2) 0.060(3) 0.000(2) 0.002(2) 0.001(2) C4 0.052(3) 0.036(3) 0.061(3) 0.008(2) 0.005(2) 0.003(2) C5 0.048(3) 0.052(3) 0.051(3) 0.003(2) -0.004(2) -0.003(2) C6 0.051(3) 0.040(3) 0.060(3) -0.005(2) -0.002(2) -0.012(2) C7 0.058(3) 0.048(3) 0.067(4) 0.001(3) -0.015(3) -0.014(2) C8 0.050(3) 0.039(3) 0.051(3) -0.001(2) -0.009(2) -0.005(2) C9 0.053(3) 0.029(2) 0.041(2) 0.0035(18) -0.009(2) -0.0046(19) C10 0.055(3) 0.037(3) 0.058(3) -0.008(2) -0.003(2) -0.003(2) C11 0.078(4) 0.036(3) 0.072(4) -0.009(2) -0.005(3) 0.003(3) C12 0.046(3) 0.030(2) 0.041(2) -0.0003(18) -0.0055(19) -0.0018(18) C13 0.043(2) 0.033(2) 0.043(2) -0.0001(18) -0.0103(19) -0.0007(18) C14 0.043(2) 0.031(2) 0.041(2) 0.0019(18) -0.0063(18) 0.0015(19) C15 0.060(3) 0.040(3) 0.054(3) 0.008(2) -0.016(2) 0.000(2) C16 0.053(3) 0.035(2) 0.046(3) -0.0017(19) -0.010(2) -0.001(2) C17 0.039(2) 0.030(2) 0.042(2) 0.0029(18) -0.0058(18) -0.0017(18) C18 0.046(3) 0.043(2) 0.044(3) -0.004(2) -0.005(2) 0.004(2) C19 0.059(3) 0.040(3) 0.060(3) -0.010(2) 0.000(3) 0.009(2) F1 0.083(2) 0.0478(18) 0.073(2) -0.0015(15) -0.0269(18) 0.0030(15) F2 0.072(2) 0.0448(17) 0.079(2) 0.0163(16) -0.0034(17) 0.0076(15) F3 0.068(2) 0.077(2) 0.072(2) 0.0045(17) -0.0241(17) -0.0012(17) F4 0.084(2) 0.0488(17) 0.081(2) -0.0091(16) -0.0119(18) -0.0190(17) I1 0.0701(3) 0.03320(19) 0.0740(3) 0.00357(15) 0.00394(18) 0.00414(14) I2 0.0660(3) 0.0344(2) 0.0760(3) -0.00686(15) -0.00330(18) -0.00265(14) N1 0.079(3) 0.037(2) 0.072(3) -0.006(2) -0.014(3) -0.013(2) N2 0.055(3) 0.035(2) 0.072(3) 0.003(2) -0.008(2) 0.0049(18) _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. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C20 1.660(9) . ? Cl1 C20 1.660(9) 2_656 ? Cl2 Cl3 1.38(2) 2_656 ? Cl2 C20 1.626(10) . ? Cl3 Cl2 1.38(2) 2_656 ? Cl3 C20 1.620(10) . ? Cl3 C20 1.98(2) 2_656 ? C20 C20 1.49(5) 2_656 ? C20 Cl3 1.98(2) 2_656 ? C20 H20A 0.9600 . ? C1 C6 1.364(7) . ? C1 C2 1.383(7) . ? C1 I1 2.095(5) . ? C2 F1 1.353(6) . ? C2 C3 1.376(6) . ? C3 C4 1.377(8) . ? C3 I2 2.096(5) . ? C4 F2 1.337(6) . ? C4 C5 1.369(7) . ? C5 F3 1.343(6) . ? C5 C6 1.383(7) . ? C6 F4 1.350(6) . ? C7 N1 1.331(7) . ? C7 C8 1.389(7) . ? C7 H7 0.9300 . ? C8 C9 1.391(7) . ? C8 H8 0.9300 . ? C9 C10 1.386(7) . ? C9 C12 1.490(6) . ? C10 C11 1.379(7) . ? C10 H10 0.9300 . ? C11 N1 1.325(7) . ? C11 H11 0.9300 . ? C12 C13 1.400(6) . ? C12 C12 1.403(9) 2_656 ? C13 C14 1.388(6) . ? C13 H13 0.9300 . ? C14 C14 1.407(8) 2_656 ? C14 C17 1.497(6) . ? C15 N2 1.326(7) . ? C15 C16 1.386(7) . ? C15 H15 0.9300 . ? C16 C17 1.377(6) . ? C16 H16 0.9300 . ? C17 C18 1.385(6) . ? C18 C19 1.377(7) . ? C18 H18 0.9300 . ? C19 N2 1.324(7) . ? C19 H19 0.9300 . ? _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 C20 Cl1 C20 53.1(18) . 2_656 ? Cl3 Cl2 C20 82.1(12) 2_656 . ? Cl2 Cl3 C20 98.7(10) 2_656 . ? Cl2 Cl3 C20 54.3(6) 2_656 2_656 ? C20 Cl3 C20 47.4(14) . 2_656 ? C20 C20 Cl3 79.2(9) 2_656 . ? C20 C20 Cl2 94.2(16) 2_656 . ? Cl3 C20 Cl2 114.5(8) . . ? C20 C20 Cl1 63.4(9) 2_656 . ? Cl3 C20 Cl1 119.6(9) . . ? Cl2 C20 Cl1 113.9(8) . . ? C20 C20 Cl3 53.4(9) 2_656 2_656 ? Cl3 C20 Cl3 89.8(11) . 2_656 ? Cl2 C20 Cl3 43.6(9) . 2_656 ? Cl1 C20 Cl3 101.8(12) . 2_656 ? C20 C20 H20A 162.0 2_656 . ? Cl3 C20 H20A 101.2 . . ? Cl2 C20 H20A 101.8 . . ? Cl1 C20 H20A 101.9 . . ? Cl3 C20 H20A 144.2 2_656 . ? C6 C1 C2 115.9(5) . . ? C6 C1 I1 122.3(4) . . ? C2 C1 I1 121.7(4) . . ? F1 C2 C3 117.9(4) . . ? F1 C2 C1 117.5(4) . . ? C3 C2 C1 124.6(5) . . ? C2 C3 C4 116.5(4) . . ? C2 C3 I2 122.2(4) . . ? C4 C3 I2 121.3(3) . . ? F2 C4 C5 118.2(5) . . ? F2 C4 C3 120.4(4) . . ? C5 C4 C3 121.4(4) . . ? F3 C5 C4 120.5(5) . . ? F3 C5 C6 120.3(5) . . ? C4 C5 C6 119.2(5) . . ? F4 C6 C1 120.3(5) . . ? F4 C6 C5 117.4(4) . . ? C1 C6 C5 122.2(4) . . ? N1 C7 C8 123.1(5) . . ? N1 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C7 C8 C9 119.3(5) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 117.1(4) . . ? C10 C9 C12 122.3(4) . . ? C8 C9 C12 120.5(4) . . ? C11 C10 C9 119.4(5) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? N1 C11 C10 123.7(5) . . ? N1 C11 H11 118.1 . . ? C10 C11 H11 118.1 . . ? C13 C12 C12 118.3(2) . 2_656 ? C13 C12 C9 117.3(4) . . ? C12 C12 C9 124.3(2) 2_656 . ? C14 C13 C12 123.1(4) . . ? C14 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? C13 C14 C14 118.5(2) . 2_656 ? C13 C14 C17 118.4(4) . . ? C14 C14 C17 123.1(2) 2_656 . ? N2 C15 C16 124.0(5) . . ? N2 C15 H15 118.0 . . ? C16 C15 H15 118.0 . . ? C17 C16 C15 118.8(5) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 117.3(4) . . ? C16 C17 C14 120.5(4) . . ? C18 C17 C14 122.2(4) . . ? C19 C18 C17 119.6(4) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? N2 C19 C18 123.5(5) . . ? N2 C19 H19 118.3 . . ? C18 C19 H19 118.3 . . ? C11 N1 C7 117.4(4) . . ? C19 N2 C15 116.7(4) . . ? _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 Cl2 Cl3 C20 C20 -19.6(9) 2_656 . . 2_656 ? Cl2 Cl3 C20 Cl2 -109.3(16) 2_656 . . . ? C20 Cl3 C20 Cl2 -89.7(18) 2_656 . . . ? Cl2 Cl3 C20 Cl1 31.3(19) 2_656 . . . ? C20 Cl3 C20 Cl1 50.8(13) 2_656 . . . ? Cl2 Cl3 C20 Cl3 -72.2(11) 2_656 . . 2_656 ? C20 Cl3 C20 Cl3 -52.7(8) 2_656 . . 2_656 ? Cl3 Cl2 C20 C20 -19.1(8) 2_656 . . 2_656 ? Cl3 Cl2 C20 Cl3 60.9(18) 2_656 . . . ? Cl3 Cl2 C20 Cl1 -81.9(16) 2_656 . . . ? C20 Cl1 C20 Cl3 -58.4(13) 2_656 . . . ? C20 Cl1 C20 Cl2 82.4(19) 2_656 . . . ? C20 Cl1 C20 Cl3 38.2(8) 2_656 . . 2_656 ? C6 C1 C2 F1 -177.0(5) . . . . ? I1 C1 C2 F1 6.1(7) . . . . ? C6 C1 C2 C3 2.3(8) . . . . ? I1 C1 C2 C3 -174.6(4) . . . . ? F1 C2 C3 C4 178.9(5) . . . . ? C1 C2 C3 C4 -0.4(8) . . . . ? F1 C2 C3 I2 -0.9(7) . . . . ? C1 C2 C3 I2 179.8(4) . . . . ? C2 C3 C4 F2 177.3(5) . . . . ? I2 C3 C4 F2 -2.8(7) . . . . ? C2 C3 C4 C5 -2.5(8) . . . . ? I2 C3 C4 C5 177.3(4) . . . . ? F2 C4 C5 F3 1.3(8) . . . . ? C3 C4 C5 F3 -178.9(5) . . . . ? F2 C4 C5 C6 -176.5(5) . . . . ? C3 C4 C5 C6 3.4(8) . . . . ? C2 C1 C6 F4 -179.7(5) . . . . ? I1 C1 C6 F4 -2.9(7) . . . . ? C2 C1 C6 C5 -1.4(8) . . . . ? I1 C1 C6 C5 175.4(4) . . . . ? F3 C5 C6 F4 -0.7(8) . . . . ? C4 C5 C6 F4 177.1(5) . . . . ? F3 C5 C6 C1 -179.1(5) . . . . ? C4 C5 C6 C1 -1.3(8) . . . . ? N1 C7 C8 C9 -0.9(8) . . . . ? C7 C8 C9 C10 0.2(7) . . . . ? C7 C8 C9 C12 177.9(5) . . . . ? C8 C9 C10 C11 0.3(7) . . . . ? C12 C9 C10 C11 -177.4(5) . . . . ? C9 C10 C11 N1 0.0(9) . . . . ? C10 C9 C12 C13 133.9(5) . . . . ? C8 C9 C12 C13 -43.8(7) . . . . ? C10 C9 C12 C12 -43.6(9) . . . 2_656 ? C8 C9 C12 C12 138.8(6) . . . 2_656 ? C12 C12 C13 C14 2.4(9) 2_656 . . . ? C9 C12 C13 C14 -175.2(4) . . . . ? C12 C13 C14 C14 1.2(9) . . . 2_656 ? C12 C13 C14 C17 -177.2(4) . . . . ? N2 C15 C16 C17 0.6(8) . . . . ? C15 C16 C17 C18 2.1(7) . . . . ? C15 C16 C17 C14 -178.4(4) . . . . ? C13 C14 C17 C16 -45.3(7) . . . . ? C14 C14 C17 C16 136.3(6) 2_656 . . . ? C13 C14 C17 C18 134.2(5) . . . . ? C14 C14 C17 C18 -44.2(8) 2_656 . . . ? C16 C17 C18 C19 -3.1(7) . . . . ? C14 C17 C18 C19 177.3(5) . . . . ? C17 C18 C19 N2 1.6(8) . . . . ? C10 C11 N1 C7 -0.7(9) . . . . ? C8 C7 N1 C11 1.2(8) . . . . ? C18 C19 N2 C15 1.1(8) . . . . ? C16 C15 N2 C19 -2.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.889 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.086 data_2c _database_code_depnum_ccdc_archive 'CCDC 888804' #TrackingRef '- 1a-2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H18 F6 I6 N4' _chemical_formula_weight 1405.96 _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' I I -0.4742 1.8119 '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_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3457(10) _cell_length_b 10.8381(11) _cell_length_c 11.4689(12) _cell_angle_alpha 114.1730(10) _cell_angle_beta 102.9140(10) _cell_angle_gamma 91.2080(10) _cell_volume 1024.69(19) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5303 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 646 _exptl_absorpt_coefficient_mu 4.608 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2954 _exptl_absorpt_correction_T_max 0.3921 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7614 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3779 _reflns_number_gt 3394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0314P)^2^+0.9424P] 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 3779 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0601 _refine_ls_wR_factor_gt 0.0575 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _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 0.0011(4) 0.6521(3) -0.0399(3) 0.0418(7) Uani 1 1 d . . . C2 C 0.1489(4) 0.6401(3) -0.0065(3) 0.0413(8) Uani 1 1 d . . . C3 C 0.2303(4) 0.6794(3) 0.1230(3) 0.0415(7) Uani 1 1 d . . . C4 C 0.1551(4) 0.7297(3) 0.2204(3) 0.0419(7) Uani 1 1 d . . . C5 C 0.0049(4) 0.7398(3) 0.1931(3) 0.0431(8) Uani 1 1 d . . . C6 C -0.0683(4) 0.7017(4) 0.0627(4) 0.0452(8) Uani 1 1 d . . . C7 C 0.8339(5) 0.3621(5) 0.4311(4) 0.0626(11) Uani 1 1 d . . . H7 H 0.9278 0.3637 0.4809 0.075 Uiso 1 1 calc R . . C8 C 0.7738(4) 0.2454(4) 0.3184(4) 0.0540(9) Uani 1 1 d . . . H8 H 0.8273 0.1715 0.2933 0.065 Uiso 1 1 calc R . . C9 C 0.6340(4) 0.2385(3) 0.2430(3) 0.0382(7) Uani 1 1 d . . . C10 C 0.5627(4) 0.3536(4) 0.2844(4) 0.0530(9) Uani 1 1 d . . . H10 H 0.4689 0.3550 0.2361 0.064 Uiso 1 1 calc R . . C11 C 0.6333(5) 0.4669(4) 0.3993(4) 0.0608(10) Uani 1 1 d . . . H11 H 0.5841 0.5435 0.4258 0.073 Uiso 1 1 calc R . . C12 C 0.5642(4) 0.1131(3) 0.1201(3) 0.0380(7) Uani 1 1 d . . . C13 C 0.4358(4) 0.0340(3) 0.1076(3) 0.0387(7) Uani 1 1 d . . . C14 C 0.3747(4) -0.0768(3) -0.0130(3) 0.0399(7) Uani 1 1 d . . . H14 H 0.2889 -0.1287 -0.0221 0.048 Uiso 1 1 calc R . . C15 C 0.1600(5) 0.0810(5) 0.3130(5) 0.0695(13) Uani 1 1 d . . . H15 H 0.0579 0.0784 0.3002 0.083 Uiso 1 1 calc R . . C16 C 0.2169(4) 0.0569(4) 0.2048(4) 0.0526(9) Uani 1 1 d . . . H16 H 0.1541 0.0385 0.1227 0.063 Uiso 1 1 calc R . . C17 C 0.3682(4) 0.0605(3) 0.2206(3) 0.0412(8) Uani 1 1 d . . . C18 C 0.4529(5) 0.0845(4) 0.3456(4) 0.0539(9) Uani 1 1 d . . . H18 H 0.5549 0.0850 0.3613 0.065 Uiso 1 1 calc R . . C19 C 0.3842(6) 0.1077(4) 0.4470(4) 0.0647(11) Uani 1 1 d . . . H19 H 0.4436 0.1246 0.5300 0.078 Uiso 1 1 calc R . . F1 F 0.2196(2) 0.5885(2) -0.1034(2) 0.0553(5) Uani 1 1 d . . . F2 F 0.2308(2) 0.7688(2) 0.34696(19) 0.0567(5) Uani 1 1 d . . . F3 F -0.2136(2) 0.7133(3) 0.0327(2) 0.0664(6) Uani 1 1 d . . . I1 I -0.11117(3) 0.59466(2) -0.23840(2) 0.05016(8) Uani 1 1 d . . . I2 I 0.45621(3) 0.66599(3) 0.16583(3) 0.06361(10) Uani 1 1 d . . . I3 I -0.10555(3) 0.80805(3) 0.34548(2) 0.05560(9) Uani 1 1 d . . . N1 N 0.7664(4) 0.4724(4) 0.4731(3) 0.0603(9) Uani 1 1 d . . . N2 N 0.2409(5) 0.1075(4) 0.4333(4) 0.0683(10) Uani 1 1 d . . . _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 0.048(2) 0.0404(18) 0.0326(16) 0.0108(14) 0.0121(14) -0.0009(14) C2 0.052(2) 0.0363(17) 0.0365(17) 0.0099(14) 0.0233(15) 0.0030(14) C3 0.0416(18) 0.0399(17) 0.0415(18) 0.0131(15) 0.0162(15) 0.0031(14) C4 0.051(2) 0.0371(17) 0.0340(17) 0.0089(14) 0.0157(15) 0.0006(14) C5 0.051(2) 0.0404(18) 0.0382(18) 0.0104(15) 0.0235(16) 0.0034(15) C6 0.0410(19) 0.0457(19) 0.048(2) 0.0154(16) 0.0180(15) 0.0040(15) C7 0.049(2) 0.077(3) 0.049(2) 0.020(2) 0.0009(18) -0.004(2) C8 0.042(2) 0.057(2) 0.050(2) 0.0115(18) 0.0094(17) 0.0064(17) C9 0.0367(16) 0.0453(18) 0.0337(16) 0.0158(14) 0.0135(13) -0.0001(14) C10 0.051(2) 0.056(2) 0.044(2) 0.0150(18) 0.0086(17) 0.0082(17) C11 0.072(3) 0.050(2) 0.049(2) 0.0113(18) 0.014(2) 0.011(2) C12 0.0367(17) 0.0427(18) 0.0358(17) 0.0155(14) 0.0136(13) 0.0032(13) C13 0.0381(17) 0.0433(18) 0.0372(17) 0.0160(14) 0.0166(14) 0.0040(14) C14 0.0352(17) 0.0452(18) 0.0402(18) 0.0165(15) 0.0155(14) -0.0018(14) C15 0.067(3) 0.070(3) 0.101(4) 0.045(3) 0.058(3) 0.029(2) C16 0.053(2) 0.056(2) 0.059(2) 0.0265(19) 0.0288(19) 0.0115(17) C17 0.050(2) 0.0356(17) 0.0423(18) 0.0137(14) 0.0257(16) 0.0037(14) C18 0.055(2) 0.066(2) 0.045(2) 0.0212(18) 0.0245(18) 0.0003(18) C19 0.086(3) 0.066(3) 0.045(2) 0.019(2) 0.034(2) 0.004(2) F1 0.0590(13) 0.0654(13) 0.0412(11) 0.0139(10) 0.0286(10) 0.0106(10) F2 0.0594(13) 0.0664(14) 0.0339(11) 0.0110(10) 0.0125(9) 0.0031(11) F3 0.0437(12) 0.0909(18) 0.0588(14) 0.0233(13) 0.0182(10) 0.0121(12) I1 0.05816(16) 0.05017(15) 0.04013(13) 0.01864(11) 0.01041(11) -0.00023(11) I2 0.04840(16) 0.0794(2) 0.05679(17) 0.02013(14) 0.01792(12) 0.01779(13) I3 0.06207(17) 0.05696(16) 0.04871(15) 0.01320(12) 0.03402(12) 0.00768(12) N1 0.072(2) 0.054(2) 0.0414(18) 0.0111(15) 0.0076(16) -0.0040(17) N2 0.099(3) 0.061(2) 0.067(2) 0.0281(19) 0.058(2) 0.020(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. ; _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 C2 1.372(5) . ? C1 C6 1.390(5) . ? C1 I1 2.101(3) . ? C2 F1 1.349(4) . ? C2 C3 1.389(5) . ? C3 C4 1.382(5) . ? C3 I2 2.080(3) . ? C4 F2 1.346(4) . ? C4 C5 1.385(5) . ? C5 C6 1.379(5) . ? C5 I3 2.108(3) . ? C6 F3 1.346(4) . ? C7 N1 1.325(6) . ? C7 C8 1.375(6) . ? C7 H7 0.9300 . ? C8 C9 1.378(5) . ? C8 H8 0.9300 . ? C9 C10 1.385(5) . ? C9 C12 1.498(5) . ? C10 C11 1.390(5) . ? C10 H10 0.9300 . ? C11 N1 1.324(5) . ? C11 H11 0.9300 . ? C12 C14 1.385(4) 2_655 ? C12 C13 1.405(4) . ? C13 C14 1.393(5) . ? C13 C17 1.494(4) . ? C14 C12 1.385(4) 2_655 ? C14 H14 0.9300 . ? C15 N2 1.326(6) . ? C15 C16 1.388(6) . ? C15 H15 0.9300 . ? C16 C17 1.382(5) . ? C16 H16 0.9300 . ? C17 C18 1.388(5) . ? C18 C19 1.389(5) . ? C18 H18 0.9300 . ? C19 N2 1.313(6) . ? C19 H19 0.9300 . ? _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 C2 C1 C6 116.9(3) . . ? C2 C1 I1 120.3(2) . . ? C6 C1 I1 122.8(3) . . ? F1 C2 C1 118.8(3) . . ? F1 C2 C3 118.0(3) . . ? C1 C2 C3 123.2(3) . . ? C4 C3 C2 117.0(3) . . ? C4 C3 I2 122.3(3) . . ? C2 C3 I2 120.7(2) . . ? F2 C4 C3 118.5(3) . . ? F2 C4 C5 118.7(3) . . ? C3 C4 C5 122.8(3) . . ? C6 C5 C4 117.1(3) . . ? C6 C5 I3 122.0(3) . . ? C4 C5 I3 120.9(2) . . ? F3 C6 C5 118.8(3) . . ? F3 C6 C1 118.2(3) . . ? C5 C6 C1 123.0(3) . . ? N1 C7 C8 124.2(4) . . ? N1 C7 H7 117.9 . . ? C8 C7 H7 117.9 . . ? C7 C8 C9 119.6(4) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 117.0(3) . . ? C10 C9 C12 121.6(3) . . ? C8 C9 C12 121.3(3) . . ? C9 C10 C11 118.9(4) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? N1 C11 C10 124.0(4) . . ? N1 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? C14 C12 C13 118.8(3) 2_655 . ? C14 C12 C9 118.6(3) 2_655 . ? C13 C12 C9 122.5(3) . . ? C14 C13 C12 118.3(3) . . ? C14 C13 C17 119.4(3) . . ? C12 C13 C17 122.3(3) . . ? C12 C14 C13 122.9(3) 2_655 . ? C12 C14 H14 118.5 2_655 . ? C13 C14 H14 118.5 . . ? N2 C15 C16 124.6(4) . . ? N2 C15 H15 117.7 . . ? C16 C15 H15 117.7 . . ? C15 C16 C17 119.1(4) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C18 C17 C16 116.4(3) . . ? C18 C17 C13 122.0(3) . . ? C16 C17 C13 121.6(3) . . ? C17 C18 C19 119.6(4) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? N2 C19 C18 124.2(4) . . ? N2 C19 H19 117.9 . . ? C18 C19 H19 117.9 . . ? C7 N1 C11 116.3(3) . . ? C19 N2 C15 116.0(3) . . ? _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 C6 C1 C2 F1 178.0(3) . . . . ? I1 C1 C2 F1 -1.3(4) . . . . ? C6 C1 C2 C3 -2.3(5) . . . . ? I1 C1 C2 C3 178.3(3) . . . . ? F1 C2 C3 C4 -178.8(3) . . . . ? C1 C2 C3 C4 1.5(5) . . . . ? F1 C2 C3 I2 2.4(4) . . . . ? C1 C2 C3 I2 -177.3(3) . . . . ? C2 C3 C4 F2 -180.0(3) . . . . ? I2 C3 C4 F2 -1.2(4) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? I2 C3 C4 C5 179.7(3) . . . . ? F2 C4 C5 C6 178.6(3) . . . . ? C3 C4 C5 C6 -2.3(5) . . . . ? F2 C4 C5 I3 -2.2(4) . . . . ? C3 C4 C5 I3 176.9(3) . . . . ? C4 C5 C6 F3 -178.4(3) . . . . ? I3 C5 C6 F3 2.4(5) . . . . ? C4 C5 C6 C1 1.4(5) . . . . ? I3 C5 C6 C1 -177.7(3) . . . . ? C2 C1 C6 F3 -179.4(3) . . . . ? I1 C1 C6 F3 0.0(5) . . . . ? C2 C1 C6 C5 0.8(5) . . . . ? I1 C1 C6 C5 -179.9(3) . . . . ? N1 C7 C8 C9 -0.9(7) . . . . ? C7 C8 C9 C10 1.7(6) . . . . ? C7 C8 C9 C12 -179.6(3) . . . . ? C8 C9 C10 C11 -1.3(5) . . . . ? C12 C9 C10 C11 -179.9(3) . . . . ? C9 C10 C11 N1 -0.1(7) . . . . ? C10 C9 C12 C14 111.9(4) . . . 2_655 ? C8 C9 C12 C14 -66.7(5) . . . 2_655 ? C10 C9 C12 C13 -65.6(5) . . . . ? C8 C9 C12 C13 115.8(4) . . . . ? C14 C12 C13 C14 -0.8(5) 2_655 . . . ? C9 C12 C13 C14 176.7(3) . . . . ? C14 C12 C13 C17 176.0(3) 2_655 . . . ? C9 C12 C13 C17 -6.5(5) . . . . ? C12 C13 C14 C12 0.9(6) . . . 2_655 ? C17 C13 C14 C12 -176.0(3) . . . 2_655 ? N2 C15 C16 C17 -0.2(7) . . . . ? C15 C16 C17 C18 1.9(5) . . . . ? C15 C16 C17 C13 179.4(3) . . . . ? C14 C13 C17 C18 131.3(4) . . . . ? C12 C13 C17 C18 -45.5(5) . . . . ? C14 C13 C17 C16 -46.1(5) . . . . ? C12 C13 C17 C16 137.2(4) . . . . ? C16 C17 C18 C19 -2.1(6) . . . . ? C13 C17 C18 C19 -179.6(4) . . . . ? C17 C18 C19 N2 0.7(7) . . . . ? C8 C7 N1 C11 -0.5(7) . . . . ? C10 C11 N1 C7 1.0(7) . . . . ? C18 C19 N2 C15 1.0(7) . . . . ? C16 C15 N2 C19 -1.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.833 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.075 data_2b _database_code_depnum_ccdc_archive 'CCDC 888805' #TrackingRef '- 1a-2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12.67 H6 F2 I2 N1.33' _chemical_formula_weight 468.65 _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' I I -0.4742 1.8119 '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_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9547(11) _cell_length_b 11.1438(14) _cell_length_c 11.4320(14) _cell_angle_alpha 74.6900(10) _cell_angle_beta 85.6220(10) _cell_angle_gamma 69.1360(10) _cell_volume 1028.0(2) _cell_formula_units_Z 3 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4939 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.19 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 646 _exptl_absorpt_coefficient_mu 4.593 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2963 _exptl_absorpt_correction_T_max 0.3595 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7622 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3791 _reflns_number_gt 3426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0256P)^2^+1.1713P] 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 SHELXL _refine_ls_extinction_coef 0.0189(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3791 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0659 _refine_ls_wR_factor_gt 0.0642 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _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 F1 F 0.8139(3) 0.3387(3) 0.5314(2) 0.0559(6) Uani 1 1 d . . . F2 F 0.3456(3) 0.3550(3) 0.3603(3) 0.0634(7) Uani 1 1 d . . . F3 F 0.6304(3) 0.6223(3) 0.1477(2) 0.0542(6) Uani 1 1 d . . . I1 I 0.92646(4) 0.53767(4) 0.32189(3) 0.06381(13) Uani 1 1 d . . . I2 I 0.55002(4) 0.20086(3) 0.60064(3) 0.05339(12) Uani 1 1 d . . . I3 I 0.30653(3) 0.57558(3) 0.11094(2) 0.04485(11) Uani 1 1 d . . . N1 N 0.6112(5) 0.9908(5) 0.2027(4) 0.0675(12) Uani 1 1 d . . . N2 N 1.0629(4) 0.6781(3) 0.9229(3) 0.0421(8) Uani 1 1 d . . . C1 C 0.6992(7) 0.9505(6) 0.1114(5) 0.0668(14) Uani 1 1 d . . . H1 H 0.6476 0.9395 0.0495 0.080 Uiso 1 1 calc R . . C2 C 0.8609(7) 0.9243(5) 0.1031(4) 0.0601(13) Uani 1 1 d . . . H2 H 0.9165 0.8978 0.0368 0.072 Uiso 1 1 calc R . . C3 C 0.9395(5) 0.9383(4) 0.1958(4) 0.0476(10) Uani 1 1 d . . . H3 H 1.0494 0.9197 0.1933 0.057 Uiso 1 1 calc R . . C4 C 0.8533(4) 0.9800(4) 0.2917(3) 0.0345(8) Uani 1 1 d . . . C5 C 0.6903(5) 1.0050(5) 0.2896(4) 0.0500(11) Uani 1 1 d . . . H5 H 0.6314 1.0340 0.3537 0.060 Uiso 1 1 calc R . . C6 C 0.9286(4) 0.9947(4) 0.3967(3) 0.0322(8) Uani 1 1 d . . . C7 C 0.9109(4) 0.9202(4) 0.5124(3) 0.0345(8) Uani 1 1 d . . . H7 H 0.8502 0.8661 0.5208 0.041 Uiso 1 1 calc R . . C8 C 0.9799(4) 0.9235(3) 0.6156(3) 0.0316(8) Uani 1 1 d . . . C9 C 0.9171(5) 0.6743(4) 0.9509(4) 0.0438(9) Uani 1 1 d . . . H9 H 0.9041 0.6185 1.0243 0.053 Uiso 1 1 calc R . . C10 C 0.7852(5) 0.7486(4) 0.8767(4) 0.0407(9) Uani 1 1 d . . . H10 H 0.6853 0.7434 0.8994 0.049 Uiso 1 1 calc R . . C11 C 0.8044(5) 0.8312(4) 0.7676(4) 0.0392(9) Uani 1 1 d . . . H11 H 0.7168 0.8829 0.7159 0.047 Uiso 1 1 calc R . . C12 C 0.9554(4) 0.8371(4) 0.7350(3) 0.0320(8) Uani 1 1 d . . . C13 C 1.0804(4) 0.7577(4) 0.8173(3) 0.0354(8) Uani 1 1 d . . . H13 H 1.1820 0.7604 0.7974 0.042 Uiso 1 1 calc R . . C14 C 0.7292(4) 0.4791(4) 0.3375(4) 0.0396(9) Uani 1 1 d . . . C15 C 0.7073(5) 0.3870(4) 0.4383(4) 0.0406(9) Uani 1 1 d . . . C16 C 0.5800(5) 0.3419(4) 0.4484(4) 0.0412(9) Uani 1 1 d . . . C17 C 0.4708(5) 0.3960(4) 0.3529(4) 0.0409(9) Uani 1 1 d . . . C18 C 0.4819(4) 0.4915(4) 0.2505(4) 0.0386(9) Uani 1 1 d . . . C19 C 0.6138(5) 0.5300(4) 0.2455(4) 0.0391(9) Uani 1 1 d . . . _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 F1 0.0489(14) 0.0665(17) 0.0450(14) -0.0060(12) -0.0132(11) -0.0145(12) F2 0.0505(15) 0.0727(18) 0.0697(18) 0.0045(14) -0.0093(13) -0.0387(14) F3 0.0540(15) 0.0712(17) 0.0396(13) 0.0021(12) -0.0033(11) -0.0353(13) I1 0.04918(19) 0.1000(3) 0.0536(2) -0.01111(17) -0.00399(14) -0.04459(18) I2 0.0606(2) 0.03904(17) 0.04969(18) -0.00258(12) 0.00708(13) -0.01199(13) I3 0.03745(16) 0.05151(18) 0.04370(17) -0.00428(12) -0.00555(11) -0.01764(12) N1 0.051(2) 0.100(3) 0.066(3) -0.035(2) -0.005(2) -0.033(2) N2 0.047(2) 0.0411(18) 0.0346(18) -0.0006(14) -0.0052(14) -0.0167(15) C1 0.071(3) 0.090(4) 0.055(3) -0.026(3) -0.011(3) -0.038(3) C2 0.080(3) 0.079(3) 0.042(2) -0.030(2) 0.011(2) -0.043(3) C3 0.048(2) 0.054(3) 0.050(2) -0.020(2) 0.0070(19) -0.025(2) C4 0.041(2) 0.0345(19) 0.0313(19) -0.0056(15) 0.0002(15) -0.0191(16) C5 0.041(2) 0.070(3) 0.048(2) -0.024(2) 0.0042(19) -0.024(2) C6 0.0307(18) 0.0343(19) 0.0289(18) -0.0041(15) 0.0002(14) -0.0108(15) C7 0.0339(19) 0.035(2) 0.037(2) -0.0063(16) 0.0007(15) -0.0169(16) C8 0.0308(18) 0.0298(18) 0.0319(18) -0.0034(15) 0.0007(14) -0.0111(15) C9 0.059(3) 0.043(2) 0.031(2) -0.0002(17) 0.0013(18) -0.027(2) C10 0.042(2) 0.047(2) 0.036(2) -0.0068(17) 0.0082(17) -0.0238(18) C11 0.038(2) 0.040(2) 0.038(2) -0.0033(17) -0.0027(16) -0.0156(17) C12 0.0366(19) 0.0323(19) 0.0281(18) -0.0071(15) 0.0026(14) -0.0139(15) C13 0.0348(19) 0.034(2) 0.035(2) -0.0046(16) -0.0026(15) -0.0123(16) C14 0.033(2) 0.050(2) 0.040(2) -0.0153(18) 0.0012(16) -0.0161(18) C15 0.035(2) 0.042(2) 0.040(2) -0.0135(18) -0.0032(16) -0.0047(17) C16 0.040(2) 0.037(2) 0.041(2) -0.0083(17) 0.0036(17) -0.0072(17) C17 0.034(2) 0.041(2) 0.050(2) -0.0116(18) 0.0020(17) -0.0159(17) C18 0.033(2) 0.044(2) 0.039(2) -0.0079(17) -0.0031(16) -0.0145(17) C19 0.038(2) 0.043(2) 0.038(2) -0.0099(17) 0.0039(16) -0.0162(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. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C15 1.349(4) . ? F2 C17 1.343(5) . ? F3 C19 1.344(5) . ? I1 C14 2.071(4) . ? I2 C16 2.087(4) . ? I3 C18 2.105(4) . ? N1 C5 1.335(6) . ? N1 C1 1.335(7) . ? N2 C9 1.333(5) . ? N2 C13 1.332(5) . ? C1 C2 1.373(7) . ? C1 H1 0.9300 . ? C2 C3 1.387(6) . ? C2 H2 0.9300 . ? C3 C4 1.378(5) . ? C3 H3 0.9300 . ? C4 C5 1.386(5) . ? C4 C6 1.492(5) . ? C5 H5 0.9300 . ? C6 C7 1.395(5) . ? C6 C8 1.404(5) 2_776 ? C7 C8 1.386(5) . ? C7 H7 0.9300 . ? C8 C6 1.404(5) 2_776 ? C8 C12 1.500(5) . ? C9 C10 1.374(6) . ? C9 H9 0.9300 . ? C10 C11 1.381(5) . ? C10 H10 0.9300 . ? C11 C12 1.395(5) . ? C11 H11 0.9300 . ? C12 C13 1.391(5) . ? C13 H13 0.9300 . ? C14 C15 1.379(6) . ? C14 C19 1.389(6) . ? C15 C16 1.387(6) . ? C16 C17 1.380(6) . ? C17 C18 1.384(6) . ? C18 C19 1.386(5) . ? _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 C5 N1 C1 115.9(4) . . ? C9 N2 C13 117.9(3) . . ? N1 C1 C2 124.1(4) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C1 C2 C3 118.4(4) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 119.4(4) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 117.0(4) . . ? C3 C4 C6 123.0(4) . . ? C5 C4 C6 120.0(3) . . ? N1 C5 C4 125.2(4) . . ? N1 C5 H5 117.4 . . ? C4 C5 H5 117.4 . . ? C7 C6 C8 118.4(3) . 2_776 ? C7 C6 C4 118.2(3) . . ? C8 C6 C4 123.3(3) 2_776 . ? C8 C7 C6 122.9(3) . . ? C8 C7 H7 118.6 . . ? C6 C7 H7 118.6 . . ? C7 C8 C6 118.7(3) . 2_776 ? C7 C8 C12 118.2(3) . . ? C6 C8 C12 123.1(3) 2_776 . ? N2 C9 C10 123.2(4) . . ? N2 C9 H9 118.4 . . ? C10 C9 H9 118.4 . . ? C9 C10 C11 118.5(4) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C10 C11 C12 119.8(4) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 116.8(3) . . ? C13 C12 C8 122.4(3) . . ? C11 C12 C8 120.8(3) . . ? N2 C13 C12 123.8(3) . . ? N2 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C15 C14 C19 117.0(4) . . ? C15 C14 I1 121.9(3) . . ? C19 C14 I1 121.1(3) . . ? F1 C15 C14 118.8(4) . . ? F1 C15 C16 118.4(4) . . ? C14 C15 C16 122.9(4) . . ? C17 C16 C15 116.9(4) . . ? C17 C16 I2 120.7(3) . . ? C15 C16 I2 122.4(3) . . ? F2 C17 C16 118.4(4) . . ? F2 C17 C18 118.0(4) . . ? C16 C17 C18 123.7(4) . . ? C17 C18 C19 116.3(4) . . ? C17 C18 I3 121.9(3) . . ? C19 C18 I3 121.8(3) . . ? F3 C19 C14 118.1(3) . . ? F3 C19 C18 118.7(3) . . ? C14 C19 C18 123.2(4) . . ? _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 C5 N1 C1 C2 -0.1(8) . . . . ? N1 C1 C2 C3 1.0(9) . . . . ? C1 C2 C3 C4 -1.1(7) . . . . ? C2 C3 C4 C5 0.4(6) . . . . ? C2 C3 C4 C6 178.5(4) . . . . ? C1 N1 C5 C4 -0.7(8) . . . . ? C3 C4 C5 N1 0.6(7) . . . . ? C6 C4 C5 N1 -177.6(4) . . . . ? C3 C4 C6 C7 -120.7(4) . . . . ? C5 C4 C6 C7 57.4(5) . . . . ? C3 C4 C6 C8 57.4(5) . . . 2_776 ? C5 C4 C6 C8 -124.6(4) . . . 2_776 ? C8 C6 C7 C8 -0.1(6) 2_776 . . . ? C4 C6 C7 C8 178.0(3) . . . . ? C6 C7 C8 C6 0.1(6) . . . 2_776 ? C6 C7 C8 C12 -178.8(3) . . . . ? C13 N2 C9 C10 -0.3(6) . . . . ? N2 C9 C10 C11 0.1(6) . . . . ? C9 C10 C11 C12 0.3(6) . . . . ? C10 C11 C12 C13 -0.4(6) . . . . ? C10 C11 C12 C8 178.4(4) . . . . ? C7 C8 C12 C13 133.0(4) . . . . ? C6 C8 C12 C13 -45.9(5) 2_776 . . . ? C7 C8 C12 C11 -45.8(5) . . . . ? C6 C8 C12 C11 135.3(4) 2_776 . . . ? C9 N2 C13 C12 0.2(6) . . . . ? C11 C12 C13 N2 0.2(6) . . . . ? C8 C12 C13 N2 -178.6(3) . . . . ? C19 C14 C15 F1 -177.8(3) . . . . ? I1 C14 C15 F1 3.2(5) . . . . ? C19 C14 C15 C16 2.0(6) . . . . ? I1 C14 C15 C16 -177.0(3) . . . . ? F1 C15 C16 C17 178.3(3) . . . . ? C14 C15 C16 C17 -1.5(6) . . . . ? F1 C15 C16 I2 -0.9(5) . . . . ? C14 C15 C16 I2 179.3(3) . . . . ? C15 C16 C17 F2 -179.6(4) . . . . ? I2 C16 C17 F2 -0.4(5) . . . . ? C15 C16 C17 C18 -0.4(6) . . . . ? I2 C16 C17 C18 178.8(3) . . . . ? F2 C17 C18 C19 -179.2(4) . . . . ? C16 C17 C18 C19 1.7(6) . . . . ? F2 C17 C18 I3 1.6(5) . . . . ? C16 C17 C18 I3 -177.5(3) . . . . ? C15 C14 C19 F3 178.4(4) . . . . ? I1 C14 C19 F3 -2.6(5) . . . . ? C15 C14 C19 C18 -0.7(6) . . . . ? I1 C14 C19 C18 178.4(3) . . . . ? C17 C18 C19 F3 179.9(4) . . . . ? I3 C18 C19 F3 -0.9(5) . . . . ? C17 C18 C19 C14 -1.1(6) . . . . ? I3 C18 C19 C14 178.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.829 _refine_diff_density_min -0.928 _refine_diff_density_rms 0.085 data_1b _database_code_depnum_ccdc_archive 'CCDC 888806' #TrackingRef '- 1a-2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H18 F4 I2 N4' _chemical_formula_weight 788.30 _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' I I -0.4742 1.8119 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2000(11) _cell_length_b 9.4032(11) _cell_length_c 17.302(2) _cell_angle_alpha 82.1980(10) _cell_angle_beta 79.0110(10) _cell_angle_gamma 85.5660(10) _cell_volume 1453.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3861 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 24.22 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.801 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.218 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4632 _exptl_absorpt_correction_T_max 0.6653 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11130 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5379 _reflns_number_gt 4289 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0396P)^2^+1.0308P] 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 5379 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _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 I1 I 0.54960(3) 0.94682(3) 0.387022(15) 0.04892(10) Uani 1 1 d . . . I2 I -0.09455(4) 0.79073(4) 0.46726(3) 0.08498(14) Uani 1 1 d . . . N1 N 0.5748(4) 0.6150(4) -0.2239(2) 0.0611(10) Uani 1 1 d . . . N2 N 0.9145(4) 0.8212(3) 0.1064(2) 0.0538(9) Uani 1 1 d . . . N3 N 0.7807(4) 0.1262(3) 0.30271(18) 0.0487(8) Uani 1 1 d . . . N4 N 0.7244(4) -0.0916(4) -0.1009(2) 0.0597(10) Uani 1 1 d . . . F1 F 0.2042(3) 0.9364(3) 0.38261(16) 0.0718(7) Uani 1 1 d . . . F2 F 0.5503(3) 0.6808(3) 0.52306(16) 0.0751(8) Uani 1 1 d . . . F3 F 0.3364(4) 0.5176(3) 0.61015(17) 0.0897(9) Uani 1 1 d . . . F4 F 0.0559(3) 0.5644(3) 0.58622(18) 0.0869(9) Uani 1 1 d . . . C1 C 0.1238(5) 0.7509(5) 0.4827(3) 0.0533(10) Uani 1 1 d . . . C2 C 0.2370(5) 0.8323(4) 0.4391(2) 0.0499(10) Uani 1 1 d . . . C3 C 0.3825(4) 0.8133(4) 0.4505(2) 0.0465(9) Uani 1 1 d . . . C4 C 0.4124(5) 0.7059(5) 0.5085(2) 0.0525(10) Uani 1 1 d . . . C5 C 0.3028(6) 0.6219(5) 0.5527(3) 0.0608(12) Uani 1 1 d . . . C6 C 0.1618(5) 0.6457(5) 0.5397(3) 0.0609(12) Uani 1 1 d . . . C7 C 0.7208(4) 0.4045(3) -0.0525(2) 0.0334(7) Uani 1 1 d . . . C8 C 0.7513(4) 0.5065(4) -0.0070(2) 0.0354(8) Uani 1 1 d . . . H8 H 0.7481 0.6028 -0.0282 0.043 Uiso 1 1 calc R . . C9 C 0.7862(4) 0.4718(3) 0.06825(19) 0.0338(8) Uani 1 1 d . . . C10 C 0.7932(4) 0.3250(4) 0.0993(2) 0.0354(8) Uani 1 1 d . . . C11 C 0.7562(4) 0.2243(4) 0.0552(2) 0.0367(8) Uani 1 1 d . . . H11 H 0.7572 0.1282 0.0768 0.044 Uiso 1 1 calc R . . C12 C 0.7182(4) 0.2593(4) -0.0189(2) 0.0352(8) Uani 1 1 d . . . C13 C 0.5982(5) 0.5632(4) -0.1519(2) 0.0462(9) Uani 1 1 d . . . H13 H 0.5425 0.6049 -0.1092 0.055 Uiso 1 1 calc R . . C14 C 0.6990(4) 0.4521(4) -0.1354(2) 0.0365(8) Uani 1 1 d . . . C15 C 0.7809(5) 0.3911(4) -0.1994(2) 0.0479(10) Uani 1 1 d . . . H15 H 0.8507 0.3160 -0.1917 0.058 Uiso 1 1 calc R . . C16 C 0.7582(6) 0.4424(5) -0.2746(2) 0.0624(12) Uani 1 1 d . . . H16 H 0.8117 0.4023 -0.3184 0.075 Uiso 1 1 calc R . . C17 C 0.6554(6) 0.5536(5) -0.2839(3) 0.0643(13) Uani 1 1 d . . . H17 H 0.6413 0.5881 -0.3351 0.077 Uiso 1 1 calc R . . C18 C 0.8890(4) 0.7081(4) 0.0728(2) 0.0434(9) Uani 1 1 d . . . H18 H 0.9246 0.7089 0.0187 0.052 Uiso 1 1 calc R . . C19 C 0.8136(4) 0.5894(4) 0.1121(2) 0.0357(8) Uani 1 1 d . . . C20 C 0.7598(5) 0.5913(4) 0.1928(2) 0.0476(9) Uani 1 1 d . . . H20 H 0.7061 0.5159 0.2219 0.057 Uiso 1 1 calc R . . C21 C 0.7866(5) 0.7057(5) 0.2292(3) 0.0575(11) Uani 1 1 d . . . H21 H 0.7534 0.7077 0.2833 0.069 Uiso 1 1 calc R . . C22 C 0.8634(5) 0.8167(5) 0.1838(3) 0.0592(12) Uani 1 1 d . . . H22 H 0.8807 0.8936 0.2088 0.071 Uiso 1 1 calc R . . C23 C 0.7449(4) 0.1893(4) 0.2343(2) 0.0417(9) Uani 1 1 d . . . H23 H 0.6502 0.1782 0.2253 0.050 Uiso 1 1 calc R . . C24 C 0.8398(4) 0.2702(4) 0.1762(2) 0.0353(8) Uani 1 1 d . . . C25 C 0.9789(5) 0.2882(5) 0.1910(2) 0.0526(10) Uani 1 1 d . . . H25 H 1.0464 0.3421 0.1538 0.063 Uiso 1 1 calc R . . C26 C 1.0163(5) 0.2254(5) 0.2614(3) 0.0603(12) Uani 1 1 d . . . H26 H 1.1092 0.2374 0.2726 0.072 Uiso 1 1 calc R . . C27 C 0.9163(5) 0.1454(4) 0.3146(2) 0.0528(11) Uani 1 1 d . . . H27 H 0.9442 0.1020 0.3615 0.063 Uiso 1 1 calc R . . C28 C 0.7566(5) 0.0147(4) -0.0640(2) 0.0468(9) Uani 1 1 d . . . H28 H 0.8386 0.0005 -0.0391 0.056 Uiso 1 1 calc R . . C29 C 0.6750(4) 0.1454(4) -0.0604(2) 0.0375(8) Uani 1 1 d . . . C30 C 0.5514(4) 0.1630(4) -0.0963(2) 0.0467(9) Uani 1 1 d . . . H30 H 0.4910 0.2469 -0.0936 0.056 Uiso 1 1 calc R . . C31 C 0.5187(5) 0.0558(4) -0.1359(3) 0.0600(12) Uani 1 1 d . . . H31 H 0.4373 0.0669 -0.1612 0.072 Uiso 1 1 calc R . . C32 C 0.6072(6) -0.0664(5) -0.1372(3) 0.0631(12) Uani 1 1 d . . . H32 H 0.5851 -0.1372 -0.1652 0.076 Uiso 1 1 calc R . . _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 I1 0.05016(17) 0.05581(17) 0.03722(15) -0.00050(11) -0.00211(11) -0.00441(12) I2 0.0492(2) 0.0810(3) 0.1280(3) -0.0229(2) -0.0164(2) -0.00540(17) N1 0.071(3) 0.061(2) 0.051(2) 0.0067(18) -0.0209(19) 0.0039(19) N2 0.062(2) 0.0344(18) 0.070(3) -0.0108(17) -0.0201(19) -0.0065(16) N3 0.057(2) 0.0491(19) 0.0369(18) 0.0076(15) -0.0071(15) -0.0064(16) N4 0.072(3) 0.0355(18) 0.076(3) -0.0177(17) -0.018(2) -0.0005(17) F1 0.0622(17) 0.0734(17) 0.0771(18) 0.0130(14) -0.0231(14) -0.0004(14) F2 0.0610(17) 0.0870(19) 0.0735(18) 0.0173(15) -0.0239(14) 0.0011(14) F3 0.109(3) 0.0791(19) 0.0704(19) 0.0307(16) -0.0196(17) -0.0030(17) F4 0.082(2) 0.0703(18) 0.095(2) -0.0002(16) 0.0201(17) -0.0283(15) C1 0.048(2) 0.051(2) 0.061(3) -0.014(2) -0.006(2) -0.003(2) C2 0.053(3) 0.049(2) 0.048(2) -0.0078(19) -0.011(2) 0.002(2) C3 0.049(2) 0.048(2) 0.039(2) -0.0049(17) -0.0004(18) -0.0020(18) C4 0.050(3) 0.061(3) 0.045(2) -0.001(2) -0.0112(19) 0.004(2) C5 0.077(3) 0.050(3) 0.049(3) 0.007(2) -0.002(2) -0.005(2) C6 0.062(3) 0.051(3) 0.065(3) -0.009(2) 0.007(2) -0.012(2) C7 0.0371(19) 0.0298(17) 0.0318(18) -0.0021(14) -0.0036(15) -0.0015(14) C8 0.042(2) 0.0273(17) 0.0341(19) -0.0014(14) -0.0013(15) -0.0027(15) C9 0.0372(19) 0.0307(18) 0.0309(18) -0.0049(14) 0.0012(15) -0.0025(14) C10 0.0372(19) 0.0352(18) 0.0312(18) 0.0003(14) -0.0017(15) -0.0049(15) C11 0.044(2) 0.0271(17) 0.0372(19) 0.0004(14) -0.0051(16) -0.0045(15) C12 0.039(2) 0.0323(18) 0.0336(19) -0.0011(15) -0.0061(15) -0.0020(15) C13 0.053(2) 0.038(2) 0.046(2) -0.0002(17) -0.0099(18) 0.0003(18) C14 0.041(2) 0.0311(18) 0.0373(19) -0.0007(15) -0.0077(16) -0.0079(15) C15 0.050(2) 0.050(2) 0.041(2) -0.0064(18) -0.0044(18) 0.0049(19) C16 0.078(3) 0.073(3) 0.034(2) -0.010(2) -0.003(2) -0.007(3) C17 0.082(3) 0.073(3) 0.040(2) 0.008(2) -0.026(2) -0.010(3) C18 0.047(2) 0.040(2) 0.042(2) -0.0071(17) -0.0045(17) -0.0040(17) C19 0.038(2) 0.0336(18) 0.0358(19) -0.0040(15) -0.0085(15) -0.0006(15) C20 0.056(3) 0.044(2) 0.041(2) -0.0060(17) -0.0034(18) -0.0001(18) C21 0.077(3) 0.055(3) 0.043(2) -0.020(2) -0.013(2) 0.009(2) C22 0.073(3) 0.044(2) 0.072(3) -0.026(2) -0.033(3) 0.011(2) C23 0.041(2) 0.044(2) 0.038(2) 0.0033(17) -0.0079(16) -0.0030(17) C24 0.040(2) 0.0326(18) 0.0315(18) -0.0015(14) -0.0046(15) -0.0034(15) C25 0.045(2) 0.064(3) 0.046(2) 0.001(2) -0.0038(19) -0.016(2) C26 0.047(3) 0.081(3) 0.055(3) 0.001(2) -0.019(2) -0.010(2) C27 0.067(3) 0.052(2) 0.041(2) -0.0010(19) -0.021(2) 0.006(2) C28 0.049(2) 0.040(2) 0.053(2) -0.0022(18) -0.0163(19) -0.0023(18) C29 0.042(2) 0.0314(18) 0.039(2) -0.0013(15) -0.0085(16) -0.0043(15) C30 0.049(2) 0.0322(19) 0.060(3) -0.0009(18) -0.015(2) -0.0049(17) C31 0.063(3) 0.045(2) 0.082(3) -0.006(2) -0.037(3) -0.010(2) C32 0.077(3) 0.050(3) 0.072(3) -0.018(2) -0.026(3) -0.015(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. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C3 2.105(4) . ? I2 C1 2.076(4) . ? N1 C13 1.326(5) . ? N1 C17 1.329(6) . ? N2 C22 1.328(6) . ? N2 C18 1.336(5) . ? N3 C27 1.332(5) . ? N3 C23 1.337(5) . ? N4 C28 1.336(5) . ? N4 C32 1.339(6) . ? F1 C2 1.346(5) . ? F2 C4 1.337(5) . ? F3 C5 1.361(5) . ? F4 C6 1.354(5) . ? C1 C6 1.374(6) . ? C1 C2 1.381(6) . ? C2 C3 1.385(6) . ? C3 C4 1.374(5) . ? C4 C5 1.375(6) . ? C5 C6 1.354(7) . ? C7 C8 1.396(5) . ? C7 C12 1.409(5) . ? C7 C14 1.489(5) . ? C8 C9 1.391(5) . ? C8 H8 0.9300 . ? C9 C10 1.413(5) . ? C9 C19 1.486(5) . ? C10 C11 1.392(5) . ? C10 C24 1.488(5) . ? C11 C12 1.385(5) . ? C11 H11 0.9300 . ? C12 C29 1.484(5) . ? C13 C14 1.379(5) . ? C13 H13 0.9300 . ? C14 C15 1.383(5) . ? C15 C16 1.373(6) . ? C15 H15 0.9300 . ? C16 C17 1.369(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.386(5) . ? C18 H18 0.9300 . ? C19 C20 1.391(5) . ? C20 C21 1.378(6) . ? C20 H20 0.9300 . ? C21 C22 1.373(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.383(5) . ? C23 H23 0.9300 . ? C24 C25 1.380(5) . ? C25 C26 1.372(6) . ? C25 H25 0.9300 . ? C26 C27 1.362(6) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.392(5) . ? C28 H28 0.9300 . ? C29 C30 1.385(5) . ? C30 C31 1.374(6) . ? C30 H30 0.9300 . ? C31 C32 1.357(6) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? _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 C13 N1 C17 116.5(4) . . ? C22 N2 C18 116.2(4) . . ? C27 N3 C23 116.7(3) . . ? C28 N4 C32 116.4(4) . . ? C6 C1 C2 116.5(4) . . ? C6 C1 I2 121.3(3) . . ? C2 C1 I2 122.1(3) . . ? F1 C2 C1 118.3(4) . . ? F1 C2 C3 118.1(4) . . ? C1 C2 C3 123.6(4) . . ? C4 C3 C2 116.7(4) . . ? C4 C3 I1 120.8(3) . . ? C2 C3 I1 122.4(3) . . ? F2 C4 C3 120.2(4) . . ? F2 C4 C5 118.4(4) . . ? C3 C4 C5 121.3(4) . . ? C6 C5 F3 120.6(4) . . ? C6 C5 C4 119.7(4) . . ? F3 C5 C4 119.6(4) . . ? C5 C6 F4 118.1(4) . . ? C5 C6 C1 122.1(4) . . ? F4 C6 C1 119.8(4) . . ? C8 C7 C12 118.3(3) . . ? C8 C7 C14 118.9(3) . . ? C12 C7 C14 122.7(3) . . ? C9 C8 C7 123.5(3) . . ? C9 C8 H8 118.3 . . ? C7 C8 H8 118.3 . . ? C8 C9 C10 117.8(3) . . ? C8 C9 C19 119.0(3) . . ? C10 C9 C19 123.2(3) . . ? C11 C10 C9 118.4(3) . . ? C11 C10 C24 117.5(3) . . ? C9 C10 C24 124.1(3) . . ? C12 C11 C10 123.7(3) . . ? C12 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? C11 C12 C7 118.1(3) . . ? C11 C12 C29 119.9(3) . . ? C7 C12 C29 122.0(3) . . ? N1 C13 C14 125.0(4) . . ? N1 C13 H13 117.5 . . ? C14 C13 H13 117.5 . . ? C15 C14 C13 116.8(3) . . ? C15 C14 C7 122.2(3) . . ? C13 C14 C7 121.0(3) . . ? C16 C15 C14 119.3(4) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C17 C16 C15 118.8(4) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? N1 C17 C16 123.6(4) . . ? N1 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? N2 C18 C19 125.2(4) . . ? N2 C18 H18 117.4 . . ? C19 C18 H18 117.4 . . ? C18 C19 C20 116.3(3) . . ? C18 C19 C9 120.8(3) . . ? C20 C19 C9 122.8(3) . . ? C21 C20 C19 119.6(4) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C22 C21 C20 118.5(4) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? N2 C22 C21 124.1(4) . . ? N2 C22 H22 117.9 . . ? C21 C22 H22 117.9 . . ? N3 C23 C24 124.2(4) . . ? N3 C23 H23 117.9 . . ? C24 C23 H23 117.9 . . ? C23 C24 C25 117.3(3) . . ? C23 C24 C10 119.7(3) . . ? C25 C24 C10 122.9(3) . . ? C26 C25 C24 119.1(4) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? C27 C26 C25 119.4(4) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? N3 C27 C26 123.3(4) . . ? N3 C27 H27 118.4 . . ? C26 C27 H27 118.4 . . ? N4 C28 C29 124.1(4) . . ? N4 C28 H28 118.0 . . ? C29 C28 H28 118.0 . . ? C30 C29 C28 117.0(3) . . ? C30 C29 C12 121.8(3) . . ? C28 C29 C12 121.2(3) . . ? C31 C30 C29 119.5(4) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C32 C31 C30 118.8(4) . . ? C32 C31 H31 120.6 . . ? C30 C31 H31 120.6 . . ? N4 C32 C31 124.2(4) . . ? N4 C32 H32 117.9 . . ? C31 C32 H32 117.9 . . ? _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 C6 C1 C2 F1 179.9(4) . . . . ? I2 C1 C2 F1 -2.9(5) . . . . ? C6 C1 C2 C3 -0.4(6) . . . . ? I2 C1 C2 C3 176.7(3) . . . . ? F1 C2 C3 C4 -179.9(4) . . . . ? C1 C2 C3 C4 0.5(6) . . . . ? F1 C2 C3 I1 3.0(5) . . . . ? C1 C2 C3 I1 -176.6(3) . . . . ? C2 C3 C4 F2 179.9(4) . . . . ? I1 C3 C4 F2 -2.9(6) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? I1 C3 C4 C5 177.3(3) . . . . ? F2 C4 C5 C6 179.4(4) . . . . ? C3 C4 C5 C6 -0.7(7) . . . . ? F2 C4 C5 F3 0.9(6) . . . . ? C3 C4 C5 F3 -179.3(4) . . . . ? F3 C5 C6 F4 0.9(7) . . . . ? C4 C5 C6 F4 -177.6(4) . . . . ? F3 C5 C6 C1 179.3(4) . . . . ? C4 C5 C6 C1 0.8(7) . . . . ? C2 C1 C6 C5 -0.2(7) . . . . ? I2 C1 C6 C5 -177.4(4) . . . . ? C2 C1 C6 F4 178.1(4) . . . . ? I2 C1 C6 F4 1.0(6) . . . . ? C12 C7 C8 C9 3.2(5) . . . . ? C14 C7 C8 C9 -174.2(3) . . . . ? C7 C8 C9 C10 1.0(5) . . . . ? C7 C8 C9 C19 -178.7(3) . . . . ? C8 C9 C10 C11 -3.8(5) . . . . ? C19 C9 C10 C11 176.0(3) . . . . ? C8 C9 C10 C24 175.3(3) . . . . ? C19 C9 C10 C24 -4.9(5) . . . . ? C9 C10 C11 C12 2.5(5) . . . . ? C24 C10 C11 C12 -176.7(3) . . . . ? C10 C11 C12 C7 1.7(5) . . . . ? C10 C11 C12 C29 -177.7(3) . . . . ? C8 C7 C12 C11 -4.5(5) . . . . ? C14 C7 C12 C11 172.8(3) . . . . ? C8 C7 C12 C29 175.0(3) . . . . ? C14 C7 C12 C29 -7.7(5) . . . . ? C17 N1 C13 C14 0.1(6) . . . . ? N1 C13 C14 C15 -0.1(6) . . . . ? N1 C13 C14 C7 178.0(4) . . . . ? C8 C7 C14 C15 125.1(4) . . . . ? C12 C7 C14 C15 -52.1(5) . . . . ? C8 C7 C14 C13 -52.9(5) . . . . ? C12 C7 C14 C13 129.9(4) . . . . ? C13 C14 C15 C16 -0.2(6) . . . . ? C7 C14 C15 C16 -178.3(4) . . . . ? C14 C15 C16 C17 0.5(7) . . . . ? C13 N1 C17 C16 0.1(7) . . . . ? C15 C16 C17 N1 -0.4(7) . . . . ? C22 N2 C18 C19 0.5(6) . . . . ? N2 C18 C19 C20 0.7(6) . . . . ? N2 C18 C19 C9 177.6(4) . . . . ? C8 C9 C19 C18 -38.3(5) . . . . ? C10 C9 C19 C18 142.0(4) . . . . ? C8 C9 C19 C20 138.3(4) . . . . ? C10 C9 C19 C20 -41.4(5) . . . . ? C18 C19 C20 C21 -1.7(6) . . . . ? C9 C19 C20 C21 -178.5(4) . . . . ? C19 C20 C21 C22 1.5(6) . . . . ? C18 N2 C22 C21 -0.8(6) . . . . ? C20 C21 C22 N2 -0.2(7) . . . . ? C27 N3 C23 C24 0.8(6) . . . . ? N3 C23 C24 C25 -1.2(6) . . . . ? N3 C23 C24 C10 174.6(3) . . . . ? C11 C10 C24 C23 -58.1(5) . . . . ? C9 C10 C24 C23 122.8(4) . . . . ? C11 C10 C24 C25 117.5(4) . . . . ? C9 C10 C24 C25 -61.6(5) . . . . ? C23 C24 C25 C26 0.3(6) . . . . ? C10 C24 C25 C26 -175.4(4) . . . . ? C24 C25 C26 C27 0.8(7) . . . . ? C23 N3 C27 C26 0.5(6) . . . . ? C25 C26 C27 N3 -1.3(7) . . . . ? C32 N4 C28 C29 1.2(6) . . . . ? N4 C28 C29 C30 1.4(6) . . . . ? N4 C28 C29 C12 -179.4(4) . . . . ? C11 C12 C29 C30 133.7(4) . . . . ? C7 C12 C29 C30 -45.8(5) . . . . ? C11 C12 C29 C28 -45.5(5) . . . . ? C7 C12 C29 C28 135.0(4) . . . . ? C28 C29 C30 C31 -2.6(6) . . . . ? C12 C29 C30 C31 178.1(4) . . . . ? C29 C30 C31 C32 1.4(7) . . . . ? C28 N4 C32 C31 -2.7(7) . . . . ? C30 C31 C32 N4 1.4(8) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.016 _refine_diff_density_min -1.128 _refine_diff_density_rms 0.075 data_2a _database_code_depnum_ccdc_archive 'CCDC 888810' #TrackingRef '- 1a-2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H28 F15 I15 N8' _chemical_formula_weight 2977.34 _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' I I -0.4742 1.8119 '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_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2428(9) _cell_length_b 11.0863(11) _cell_length_c 18.8796(19) _cell_angle_alpha 87.9420(10) _cell_angle_beta 85.3110(10) _cell_angle_gamma 84.4280(10) _cell_volume 1918.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6710 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1338 _exptl_absorpt_coefficient_mu 6.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1691 _exptl_absorpt_correction_T_max 0.3594 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14235 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7082 _reflns_number_gt 5834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0421P)^2^+5.8134P] 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 7082 _refine_ls_number_parameters 461 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _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 C25 C 0.1999(10) 0.5017(9) 0.5231(6) 0.056(4) Uani 0.50 1 d PG . . C26 C 0.2642(12) 0.5217(9) 0.4554(6) 0.062(4) Uani 0.50 1 d PG . . C27 C 0.4143(14) 0.5213(12) 0.4445(6) 0.067(5) Uani 0.50 1 d PG . . C28 C 0.5002(13) 0.4999(13) 0.5000(7) 0.056(3) Uani 1 2 d SG . . C29 C 0.4357(12) 0.4808(11) 0.5691(6) 0.055(4) Uani 0.50 1 d PG . . C30 C 0.2856(11) 0.4812(9) 0.5799(6) 0.058(4) Uani 0.50 1 d PG . . F7 F 0.1828(13) 0.5400(11) 0.4005(6) 0.100(4) Uani 0.50 1 d P . . F8 F 0.6414(10) 0.4964(10) 0.4900(7) 0.086(3) Uani 0.50 1 d P . . F9 F 0.2234(11) 0.4580(9) 0.6426(5) 0.079(3) Uani 0.50 1 d P . . I7 I -0.02498(13) 0.49443(14) 0.53872(10) 0.0998(5) Uani 0.50 1 d P . . I8 I 0.5108(3) 0.5495(3) 0.34036(14) 0.0985(8) Uani 0.50 1 d P . . I9 I 0.5650(2) 0.4452(2) 0.65288(13) 0.0878(6) Uani 0.50 1 d P . . C1 C 0.1083(6) 0.1121(5) 0.1902(3) 0.0356(13) Uani 1 1 d . . . C2 C 0.1551(8) 0.2998(6) 0.2232(4) 0.0472(16) Uani 1 1 d . . . C3 C 0.2986(8) 0.2538(7) 0.2289(4) 0.0510(17) Uani 1 1 d . . . H3 H 0.3658 0.3029 0.2438 0.061 Uiso 1 1 calc R . . C4 C 0.3403(7) 0.1369(6) 0.2127(3) 0.0431(15) Uani 1 1 d . . . C5 C -0.0013(6) 0.0293(5) 0.1714(3) 0.0344(13) Uani 1 1 d . . . C6 C -0.1169(7) -0.1386(6) 0.1982(4) 0.0485(16) Uani 1 1 d . . . C7 C -0.1919(7) -0.1161(7) 0.1386(4) 0.0505(17) Uani 1 1 d . . . H7 H -0.2606 -0.1671 0.1276 0.061 Uiso 1 1 calc R . . C8 C -0.1642(7) -0.0173(6) 0.0956(4) 0.0478(16) Uani 1 1 d . . . C9 C 0.0991(10) 0.4271(7) 0.2389(5) 0.069(2) Uani 1 1 d . . . H9A H -0.0028 0.4392 0.2313 0.104 Uiso 0.50 1 calc PR . . H9B H 0.1514 0.4814 0.2079 0.104 Uiso 0.50 1 calc PR . . H9C H 0.1126 0.4429 0.2874 0.104 Uiso 0.50 1 calc PR . . H9D H 0.1770 0.4698 0.2531 0.104 Uiso 0.50 1 calc PR . . H9E H 0.0228 0.4276 0.2765 0.104 Uiso 0.50 1 calc PR . . H9F H 0.0615 0.4661 0.1971 0.104 Uiso 0.50 1 calc PR . . C10 C 0.4958(8) 0.0817(7) 0.2167(5) 0.062(2) Uani 1 1 d . . . H10A H 0.4974 0.0127 0.2489 0.093 Uiso 1 1 calc R . . H10B H 0.5535 0.1407 0.2334 0.093 Uiso 1 1 calc R . . H10C H 0.5351 0.0567 0.1703 0.093 Uiso 1 1 calc R . . C11 C -0.1404(13) -0.2470(9) 0.2480(6) 0.098(4) Uani 1 1 d . . . H11A H -0.0548 -0.2677 0.2732 0.147 Uiso 1 1 calc R . . H11B H -0.1587 -0.3148 0.2209 0.147 Uiso 1 1 calc R . . H11C H -0.2224 -0.2270 0.2815 0.147 Uiso 1 1 calc R . . C12 C -0.2406(11) 0.0127(8) 0.0288(5) 0.078(3) Uani 1 1 d . . . H12A H -0.2503 0.0989 0.0206 0.117 Uiso 1 1 calc R . . H12B H -0.3355 -0.0164 0.0341 0.117 Uiso 1 1 calc R . . H12C H -0.1845 -0.0254 -0.0107 0.117 Uiso 1 1 calc R . . C13 C 0.3891(7) 0.6206(6) 0.1167(3) 0.0381(13) Uani 1 1 d . . . C14 C 0.5191(7) 0.5572(6) 0.1284(3) 0.0382(14) Uani 1 1 d . . . C15 C 0.5569(7) 0.4386(6) 0.1096(3) 0.0410(14) Uani 1 1 d . . . C16 C 0.4566(7) 0.3838(6) 0.0755(3) 0.0409(14) Uani 1 1 d . . . C17 C 0.3223(7) 0.4406(6) 0.0615(3) 0.0416(14) Uani 1 1 d . . . C18 C 0.2906(7) 0.5598(6) 0.0828(3) 0.0412(14) Uani 1 1 d . . . C19 C 0.2760(7) 0.8576(6) 0.4371(3) 0.0419(14) Uani 1 1 d . . . C20 C 0.4247(7) 0.8583(6) 0.4305(4) 0.0445(15) Uani 1 1 d . . . C21 C 0.5095(7) 0.8360(6) 0.4875(4) 0.0426(15) Uani 1 1 d . . . C22 C 0.4413(7) 0.8144(6) 0.5522(4) 0.0453(15) Uani 1 1 d . . . C23 C 0.2914(8) 0.8137(6) 0.5639(3) 0.0452(15) Uani 1 1 d . . . C24 C 0.2122(7) 0.8354(6) 0.5047(3) 0.0428(15) Uani 1 1 d . . . F1 F 0.1600(4) 0.6180(4) 0.0710(2) 0.0633(12) Uani 1 1 d . . . F2 F 0.6156(4) 0.6131(4) 0.1635(2) 0.0557(10) Uani 1 1 d . . . F3 F 0.4893(5) 0.2671(4) 0.0556(2) 0.0628(11) Uani 1 1 d . . . F4 F 0.0668(4) 0.8375(4) 0.5139(2) 0.0633(12) Uani 1 1 d . . . F5 F 0.4909(5) 0.8816(4) 0.3662(2) 0.0679(12) Uani 1 1 d . . . F6 F 0.5217(5) 0.7931(5) 0.6093(3) 0.0728(13) Uani 1 1 d . . . I1 I 0.33460(5) 0.79912(4) 0.14900(3) 0.05112(13) Uani 1 1 d . . . I2 I 0.75664(5) 0.34594(4) 0.13305(3) 0.05823(15) Uani 1 1 d . . . I3 I 0.16892(6) 0.35077(5) 0.01535(3) 0.06465(16) Uani 1 1 d . . . I4 I 0.15010(5) 0.89365(5) 0.35068(2) 0.05507(14) Uani 1 1 d . . . I5 I 0.73722(5) 0.83421(5) 0.47358(4) 0.07259(18) Uani 1 1 d . . . I6 I 0.18570(6) 0.78813(5) 0.66402(3) 0.06480(16) Uani 1 1 d . . . N1 N 0.2457(5) 0.0635(5) 0.1927(3) 0.0395(12) Uani 1 1 d . . . N2 N 0.0573(6) 0.2273(5) 0.2031(3) 0.0413(12) Uani 1 1 d . . . N3 N -0.0681(6) 0.0574(5) 0.1121(3) 0.0467(13) Uani 1 1 d . . . N4 N -0.0196(6) -0.0651(5) 0.2160(3) 0.0415(12) Uani 1 1 d . . . _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 C25 0.051(8) 0.039(8) 0.081(11) 0.001(7) -0.008(8) -0.014(6) C26 0.063(10) 0.050(9) 0.076(11) 0.013(8) -0.021(9) -0.014(7) C27 0.103(14) 0.043(9) 0.056(10) -0.002(7) 0.006(10) -0.024(9) C28 0.051(6) 0.043(6) 0.075(8) -0.011(5) -0.005(6) -0.014(5) C29 0.056(9) 0.044(8) 0.069(10) -0.008(7) -0.016(8) -0.005(7) C30 0.059(9) 0.032(7) 0.081(11) -0.005(7) 0.003(8) -0.012(6) F7 0.100(9) 0.110(9) 0.096(8) 0.002(7) -0.050(7) -0.008(7) F8 0.051(6) 0.098(8) 0.111(9) -0.009(7) 0.003(6) -0.023(5) F9 0.082(7) 0.075(7) 0.077(7) 0.006(5) 0.019(5) -0.011(5) I7 0.0454(7) 0.0905(9) 0.1637(15) -0.0078(10) -0.0116(8) -0.0037(6) I8 0.1296(19) 0.0907(13) 0.0752(11) -0.0059(9) 0.0236(15) -0.0351(16) I9 0.0951(14) 0.0864(11) 0.0861(15) -0.0104(10) -0.0400(13) -0.0002(13) C1 0.037(3) 0.034(3) 0.035(3) 0.002(2) -0.001(2) -0.003(2) C2 0.055(4) 0.041(4) 0.047(4) -0.003(3) 0.003(3) -0.017(3) C3 0.051(4) 0.055(4) 0.051(4) -0.004(3) 0.001(3) -0.026(3) C4 0.039(3) 0.052(4) 0.040(4) 0.002(3) -0.003(3) -0.015(3) C5 0.030(3) 0.030(3) 0.041(3) -0.005(3) 0.001(2) 0.000(2) C6 0.047(4) 0.050(4) 0.053(4) -0.003(3) -0.008(3) -0.021(3) C7 0.043(4) 0.053(4) 0.060(4) -0.016(3) -0.013(3) -0.010(3) C8 0.044(4) 0.047(4) 0.054(4) -0.014(3) -0.018(3) 0.003(3) C9 0.078(6) 0.042(4) 0.090(6) -0.021(4) 0.007(5) -0.014(4) C10 0.037(4) 0.061(5) 0.092(6) 0.002(4) -0.016(4) -0.011(3) C11 0.130(9) 0.085(7) 0.095(7) 0.031(6) -0.043(7) -0.071(7) C12 0.095(7) 0.073(6) 0.072(6) -0.011(5) -0.049(5) 0.002(5) C13 0.040(3) 0.036(3) 0.037(3) -0.004(3) 0.000(3) 0.001(3) C14 0.039(3) 0.041(3) 0.036(3) 0.000(3) 0.000(3) -0.011(3) C15 0.035(3) 0.042(4) 0.044(4) 0.004(3) 0.001(3) 0.001(3) C16 0.044(4) 0.039(3) 0.039(3) 0.001(3) 0.004(3) -0.006(3) C17 0.048(4) 0.045(4) 0.034(3) -0.005(3) -0.006(3) -0.010(3) C18 0.037(3) 0.044(4) 0.042(4) 0.000(3) -0.002(3) -0.002(3) C19 0.037(3) 0.046(4) 0.044(4) 0.000(3) -0.012(3) -0.007(3) C20 0.040(4) 0.041(4) 0.052(4) -0.001(3) 0.002(3) -0.006(3) C21 0.030(3) 0.039(3) 0.060(4) -0.004(3) -0.006(3) -0.006(3) C22 0.045(4) 0.043(4) 0.051(4) 0.000(3) -0.019(3) -0.006(3) C23 0.054(4) 0.043(4) 0.039(4) 0.000(3) -0.003(3) -0.007(3) C24 0.040(4) 0.043(4) 0.046(4) 0.000(3) -0.003(3) -0.008(3) F1 0.043(2) 0.068(3) 0.079(3) -0.015(2) -0.026(2) 0.013(2) F2 0.047(2) 0.058(2) 0.067(3) -0.010(2) -0.0193(19) -0.0096(18) F3 0.069(3) 0.041(2) 0.078(3) -0.012(2) -0.003(2) -0.0002(19) F4 0.033(2) 0.101(4) 0.057(3) 0.006(2) -0.0058(18) -0.012(2) F5 0.057(3) 0.086(3) 0.058(3) 0.012(2) 0.011(2) -0.010(2) F6 0.064(3) 0.089(3) 0.069(3) 0.001(2) -0.032(2) -0.001(2) I1 0.0541(3) 0.0438(3) 0.0545(3) -0.0122(2) -0.0073(2) 0.0063(2) I2 0.0394(2) 0.0516(3) 0.0800(4) 0.0131(2) -0.0012(2) 0.0057(2) I3 0.0626(3) 0.0695(3) 0.0670(3) -0.0128(3) -0.0152(3) -0.0202(3) I4 0.0556(3) 0.0646(3) 0.0459(3) 0.0030(2) -0.0132(2) -0.0041(2) I5 0.0348(3) 0.0609(3) 0.1235(5) -0.0133(3) -0.0065(3) -0.0078(2) I6 0.0753(4) 0.0752(4) 0.0434(3) 0.0020(2) 0.0019(2) -0.0111(3) N1 0.032(3) 0.041(3) 0.047(3) 0.000(2) -0.007(2) -0.008(2) N2 0.044(3) 0.035(3) 0.043(3) -0.006(2) 0.005(2) -0.003(2) N3 0.048(3) 0.041(3) 0.053(3) -0.007(3) -0.017(3) 0.004(2) N4 0.044(3) 0.042(3) 0.041(3) 0.001(2) -0.005(2) -0.015(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. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C25 C26 1.385(7) . ? C25 C30 1.385(7) . ? C25 F8 1.470(13) 2_666 ? C25 I7 2.066(10) 2_566 ? C25 I7 2.084(9) . ? C26 F7 1.328(14) . ? C26 C27 1.385(7) . ? C26 F8 1.401(15) 2_666 ? C26 I7 2.229(11) 2_566 ? C26 I9 2.517(12) 2_666 ? C27 F8 1.314(15) 2_666 ? C27 C28 1.366(7) . ? C27 C29 1.39(3) 2_666 ? C27 I9 1.861(11) 2_666 ? C27 I8 2.118(11) . ? C28 F8 1.300(15) . ? C28 F8 1.303(15) 2_666 ? C28 C27 1.36(3) 2_666 ? C28 C29 1.407(7) . ? C28 C29 1.41(3) 2_666 ? C29 F8 1.375(16) 2_666 ? C29 C30 1.385(7) . ? C29 C27 1.39(3) 2_666 ? C29 I8 1.829(12) 2_666 ? C29 I9 2.064(11) . ? C30 F9 1.302(13) . ? C30 F8 1.458(15) 2_666 ? C30 I8 2.494(11) 2_666 ? F7 I7 1.842(13) 2_566 ? F8 C27 1.31(2) 2_666 ? F8 C29 1.38(2) 2_666 ? F8 C26 1.40(3) 2_666 ? F8 C30 1.46(2) 2_666 ? F8 C25 1.470(13) 2_666 ? I7 I7 1.501(4) 2_566 ? I7 F7 1.842(14) 2_566 ? I7 C25 2.066(10) 2_566 ? I7 C26 2.23(3) 2_566 ? I8 I9 0.699(2) 2_666 ? I8 C29 1.829(18) 2_666 ? I8 C30 2.49(3) 2_666 ? I9 I8 0.699(2) 2_666 ? I9 C27 1.861(18) 2_666 ? I9 C26 2.52(2) 2_666 ? C1 N1 1.334(8) . ? C1 N2 1.342(8) . ? C1 C5 1.503(8) . ? C2 N2 1.351(8) . ? C2 C3 1.385(10) . ? C2 C9 1.487(10) . ? C3 C4 1.354(10) . ? C3 H3 0.9300 . ? C4 N1 1.336(8) . ? C4 C10 1.513(9) . ? C5 N4 1.334(8) . ? C5 N3 1.335(8) . ? C6 N4 1.341(8) . ? C6 C7 1.371(9) . ? C6 C11 1.521(11) . ? C7 C8 1.372(10) . ? C7 H7 0.9300 . ? C8 N3 1.333(9) . ? C8 C12 1.506(10) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C9 H9D 0.9600 . ? C9 H9E 0.9600 . ? C9 H9F 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.363(9) . ? C13 C18 1.392(9) . ? C13 I1 2.094(6) . ? C14 F2 1.361(7) . ? C14 C15 1.378(9) . ? C15 C16 1.371(9) . ? C15 I2 2.096(6) . ? C16 F3 1.359(7) . ? C16 C17 1.377(9) . ? C17 C18 1.392(9) . ? C17 I3 2.073(6) . ? C18 F1 1.344(7) . ? C19 C20 1.371(9) . ? C19 C24 1.385(9) . ? C19 I4 2.086(6) . ? C20 F5 1.341(8) . ? C20 C21 1.385(9) . ? C21 C22 1.352(10) . ? C21 I5 2.098(6) . ? C22 F6 1.359(7) . ? C22 C23 1.386(9) . ? C23 C24 1.386(9) . ? C23 I6 2.078(7) . ? C24 F4 1.339(7) . ? _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 C26 C25 C30 120.0 . . ? C26 C25 F8 58.7(5) . 2_666 ? C30 C25 F8 61.3(5) . 2_666 ? C26 C25 I7 77.7(6) . 2_566 ? C30 C25 I7 161.3(6) . 2_566 ? F8 C25 I7 136.1(8) 2_666 2_566 ? C26 C25 I7 120.0(6) . . ? C30 C25 I7 120.0(6) . . ? F8 C25 I7 177.9(9) 2_666 . ? I7 C25 I7 42.4(2) 2_566 . ? F7 C26 C27 119.7(10) . . ? F7 C26 C25 120.3(10) . . ? C27 C26 C25 120.0 . . ? F7 C26 F8 176.0(12) . 2_666 ? C27 C26 F8 56.3(5) . 2_666 ? C25 C26 F8 63.7(5) . 2_666 ? F7 C26 I7 55.7(7) . 2_566 ? C27 C26 I7 172.5(6) . 2_566 ? C25 C26 I7 64.9(5) . 2_566 ? F8 C26 I7 128.3(8) 2_666 2_566 ? F7 C26 I9 73.1(8) . 2_666 ? C27 C26 I9 46.6(5) . 2_666 ? C25 C26 I9 166.6(5) . 2_666 ? F8 C26 I9 102.9(7) 2_666 2_666 ? I7 C26 I9 128.5(4) 2_566 2_666 ? F8 C27 C28 58.2(5) 2_666 . ? F8 C27 C26 62.5(5) 2_666 . ? C28 C27 C26 120.6 . . ? F8 C27 C29 119.6(16) 2_666 2_666 ? C28 C27 C29 61.4(14) . 2_666 ? C26 C27 C29 177.7(15) . 2_666 ? F8 C27 I9 163.0(10) 2_666 2_666 ? C28 C27 I9 138.8(7) . 2_666 ? C26 C27 I9 100.7(7) . 2_666 ? C29 C27 I9 77.4(10) 2_666 2_666 ? F8 C27 I8 178.1(10) 2_666 . ? C28 C27 I8 120.0(7) . . ? C26 C27 I8 119.4(7) . . ? C29 C27 I8 58.6(10) 2_666 . ? I9 C27 I8 18.85(14) 2_666 . ? F8 C28 F8 179.9(15) . 2_666 ? F8 C28 C27 59.1(10) . 2_666 ? F8 C28 C27 120.9(16) 2_666 2_666 ? F8 C28 C27 121.0(11) . . ? F8 C28 C27 59.0(6) 2_666 . ? C27 C28 C27 180(2) 2_666 . ? F8 C28 C29 119.2(11) . . ? F8 C28 C29 60.8(6) 2_666 . ? C27 C28 C29 60.1(14) 2_666 . ? C27 C28 C29 119.8 . . ? F8 C28 C29 60.9(11) . 2_666 ? F8 C28 C29 119.0(17) 2_666 2_666 ? C27 C28 C29 120.0(17) 2_666 2_666 ? C27 C28 C29 60.1(15) . 2_666 ? C29 C28 C29 180(2) . 2_666 ? F8 C29 C30 63.8(5) 2_666 . ? F8 C29 C27 114.3(16) 2_666 2_666 ? C30 C29 C27 177.7(15) . 2_666 ? F8 C29 C28 55.9(5) 2_666 . ? C30 C29 C28 119.6 . . ? C27 C29 C28 58.4(15) 2_666 . ? F8 C29 I8 164.6(9) 2_666 2_666 ? C30 C29 I8 100.9(7) . 2_666 ? C27 C29 I8 81.1(11) 2_666 2_666 ? C28 C29 I8 139.5(7) . 2_666 ? F8 C29 I9 175.8(9) 2_666 . ? C30 C29 I9 120.3(6) . . ? C27 C29 I9 61.6(10) 2_666 . ? C28 C29 I9 120.0(6) . . ? I8 C29 I9 19.50(14) 2_666 . ? F9 C30 C29 121.0(9) . . ? F9 C30 C25 118.9(9) . . ? C29 C30 C25 120.0 . . ? F9 C30 F8 178.1(11) . 2_666 ? C29 C30 F8 57.8(5) . 2_666 ? C25 C30 F8 62.2(5) . 2_666 ? F9 C30 I8 75.0(7) . 2_666 ? C29 C30 I8 46.1(5) . 2_666 ? C25 C30 I8 166.0(5) . 2_666 ? F8 C30 I8 103.8(7) 2_666 2_666 ? C26 F7 I7 87.8(8) . 2_566 ? C28 F8 C27 62.9(11) . 2_666 ? C28 F8 C29 63.3(10) . 2_666 ? C27 F8 C29 126.2(15) 2_666 2_666 ? C28 F8 C26 124.1(11) . 2_666 ? C27 F8 C26 61.2(10) 2_666 2_666 ? C29 F8 C26 172.4(16) 2_666 2_666 ? C28 F8 C30 121.7(11) . 2_666 ? C27 F8 C30 175.0(18) 2_666 2_666 ? C29 F8 C30 58.4(9) 2_666 2_666 ? C26 F8 C30 114.1(13) 2_666 2_666 ? C28 F8 C25 177.1(13) . 2_666 ? C27 F8 C25 118.9(11) 2_666 2_666 ? C29 F8 C25 114.9(11) 2_666 2_666 ? C26 F8 C25 57.6(12) 2_666 2_666 ? C30 F8 C25 56.5(13) 2_666 2_666 ? I7 I7 F7 142.4(4) 2_566 2_566 ? I7 I7 C25 69.4(3) 2_566 2_566 ? F7 I7 C25 73.8(4) 2_566 2_566 ? I7 I7 C25 68.2(3) 2_566 . ? F7 I7 C25 147.9(4) 2_566 . ? C25 I7 C25 137.6(2) 2_566 . ? I7 I7 C26 106.7(9) 2_566 2_566 ? F7 I7 C26 36.5(10) 2_566 2_566 ? C25 I7 C26 37.4(7) 2_566 2_566 ? C25 I7 C26 174.2(7) . 2_566 ? I9 I8 C29 99.6(7) 2_666 2_666 ? I9 I8 C27 59.3(5) 2_666 . ? C29 I8 C27 40.3(8) 2_666 . ? I9 I8 C30 132.5(7) 2_666 2_666 ? C29 I8 C30 33.0(4) 2_666 2_666 ? C27 I8 C30 73.4(6) . 2_666 ? I8 I9 C27 101.8(6) 2_666 2_666 ? I8 I9 C29 60.9(5) 2_666 . ? C27 I9 C29 41.0(7) 2_666 . ? I8 I9 C26 134.4(7) 2_666 2_666 ? C27 I9 C26 32.7(4) 2_666 2_666 ? C29 I9 C26 73.7(6) . 2_666 ? N1 C1 N2 126.8(6) . . ? N1 C1 C5 116.8(5) . . ? N2 C1 C5 116.4(5) . . ? N2 C2 C3 120.0(6) . . ? N2 C2 C9 116.5(7) . . ? C3 C2 C9 123.6(7) . . ? C4 C3 C2 119.5(6) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? N1 C4 C3 121.6(6) . . ? N1 C4 C10 116.2(6) . . ? C3 C4 C10 122.2(6) . . ? N4 C5 N3 127.4(6) . . ? N4 C5 C1 115.7(5) . . ? N3 C5 C1 116.8(5) . . ? N4 C6 C7 121.6(6) . . ? N4 C6 C11 116.3(6) . . ? C7 C6 C11 122.1(6) . . ? C8 C7 C6 119.0(6) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? N3 C8 C7 120.7(6) . . ? N3 C8 C12 117.0(7) . . ? C7 C8 C12 122.2(7) . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 C9 H9D 109.5 . . ? H9A C9 H9D 141.1 . . ? H9B C9 H9D 56.3 . . ? H9C C9 H9D 56.3 . . ? C2 C9 H9E 109.5 . . ? H9A C9 H9E 56.3 . . ? H9B C9 H9E 141.1 . . ? H9C C9 H9E 56.3 . . ? H9D C9 H9E 109.5 . . ? C2 C9 H9F 109.5 . . ? H9A C9 H9F 56.3 . . ? H9B C9 H9F 56.3 . . ? H9C C9 H9F 141.1 . . ? H9D C9 H9F 109.5 . . ? H9E C9 H9F 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 116.5(6) . . ? C14 C13 I1 122.8(5) . . ? C18 C13 I1 120.7(4) . . ? C13 C14 F2 117.8(6) . . ? C13 C14 C15 124.3(6) . . ? F2 C14 C15 117.9(6) . . ? C16 C15 C14 116.7(6) . . ? C16 C15 I2 121.6(5) . . ? C14 C15 I2 121.7(5) . . ? F3 C16 C15 118.8(6) . . ? F3 C16 C17 118.0(6) . . ? C15 C16 C17 123.1(6) . . ? C16 C17 C18 117.1(6) . . ? C16 C17 I3 121.8(5) . . ? C18 C17 I3 121.0(5) . . ? F1 C18 C17 119.1(6) . . ? F1 C18 C13 118.7(6) . . ? C17 C18 C13 122.2(6) . . ? C20 C19 C24 116.8(6) . . ? C20 C19 I4 121.9(5) . . ? C24 C19 I4 121.3(5) . . ? F5 C20 C19 118.8(6) . . ? F5 C20 C21 118.7(6) . . ? C19 C20 C21 122.5(6) . . ? C22 C21 C20 118.1(6) . . ? C22 C21 I5 121.1(5) . . ? C20 C21 I5 120.8(5) . . ? C21 C22 F6 119.3(6) . . ? C21 C22 C23 123.2(6) . . ? F6 C22 C23 117.5(6) . . ? C22 C23 C24 116.2(6) . . ? C22 C23 I6 123.2(5) . . ? C24 C23 I6 120.6(5) . . ? F4 C24 C19 118.6(6) . . ? F4 C24 C23 118.2(6) . . ? C19 C24 C23 123.2(6) . . ? C1 N1 C4 116.0(5) . . ? C1 N2 C2 116.0(6) . . ? C5 N3 C8 116.2(6) . . ? C5 N4 C6 115.0(6) . . ? _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 C30 C25 C26 F7 179.2(11) . . . . ? F8 C25 C26 F7 -179.8(13) 2_666 . . . ? I7 C25 C26 F7 5.6(8) 2_566 . . . ? I7 C25 C26 F7 2.0(11) . . . . ? C30 C25 C26 C27 0.0 . . . . ? F8 C25 C26 C27 0.9(6) 2_666 . . . ? I7 C25 C26 C27 -173.6(7) 2_566 . . . ? I7 C25 C26 C27 -177.2(8) . . . . ? C30 C25 C26 F8 -0.9(6) . . . 2_666 ? I7 C25 C26 F8 -174.6(9) 2_566 . . 2_666 ? I7 C25 C26 F8 -178.1(10) . . . 2_666 ? C30 C25 C26 I7 173.6(7) . . . 2_566 ? F8 C25 C26 I7 174.6(9) 2_666 . . 2_566 ? I7 C25 C26 I7 -3.6(3) . . . 2_566 ? C30 C25 C26 I9 -3(2) . . . 2_666 ? F8 C25 C26 I9 -2(2) 2_666 . . 2_666 ? I7 C25 C26 I9 -177(2) 2_566 . . 2_666 ? I7 C25 C26 I9 180(2) . . . 2_666 ? F7 C26 C27 F8 179.8(14) . . . 2_666 ? C25 C26 C27 F8 -1.0(7) . . . 2_666 ? I7 C26 C27 F8 -131(4) 2_566 . . 2_666 ? I9 C26 C27 F8 178.0(11) 2_666 . . 2_666 ? F7 C26 C27 C28 -178.5(11) . . . . ? C25 C26 C27 C28 0.7 . . . . ? F8 C26 C27 C28 1.8(7) 2_666 . . . ? I7 C26 C27 C28 -129(4) 2_566 . . . ? I9 C26 C27 C28 179.8(7) 2_666 . . . ? F7 C26 C27 C29 -29(43) . . . 2_666 ? C25 C26 C27 C29 150(44) . . . 2_666 ? F8 C26 C27 C29 151(44) 2_666 . . 2_666 ? I7 C26 C27 C29 21(46) 2_566 . . 2_666 ? I9 C26 C27 C29 -31(43) 2_666 . . 2_666 ? F7 C26 C27 I9 1.7(10) . . . 2_666 ? C25 C26 C27 I9 -179.0(7) . . . 2_666 ? F8 C26 C27 I9 -178.0(11) 2_666 . . 2_666 ? I7 C26 C27 I9 51(4) 2_566 . . 2_666 ? F7 C26 C27 I8 -0.1(11) . . . . ? C25 C26 C27 I8 179.1(8) . . . . ? F8 C26 C27 I8 -179.9(12) 2_666 . . . ? I7 C26 C27 I8 50(4) 2_566 . . . ? I9 C26 C27 I8 -1.9(2) 2_666 . . . ? F8 C27 C28 F8 -179.9(15) 2_666 . . . ? C26 C27 C28 F8 178.3(14) . . . . ? C29 C27 C28 F8 -0.4(11) 2_666 . . . ? I9 C27 C28 F8 -2.0(13) 2_666 . . . ? I8 C27 C28 F8 0.0(11) . . . . ? C26 C27 C28 F8 -1.8(7) . . . 2_666 ? C29 C27 C28 F8 179(2) 2_666 . . 2_666 ? I9 C27 C28 F8 177.8(14) 2_666 . . 2_666 ? I8 C27 C28 F8 179.8(12) . . . 2_666 ? F8 C27 C28 C27 -47(100) 2_666 . . 2_666 ? C26 C27 C28 C27 -48(100) . . . 2_666 ? C29 C27 C28 C27 133(100) 2_666 . . 2_666 ? I9 C27 C28 C27 131(100) 2_666 . . 2_666 ? I8 C27 C28 C27 133(100) . . . 2_666 ? F8 C27 C28 C29 0.4(7) 2_666 . . . ? C26 C27 C28 C29 -1.5 . . . . ? C29 C27 C28 C29 180(2) 2_666 . . . ? I9 C27 C28 C29 178.2(11) 2_666 . . . ? I8 C27 C28 C29 -179.8(8) . . . . ? F8 C27 C28 C29 -179(2) 2_666 . . 2_666 ? C26 C27 C28 C29 179(2) . . . 2_666 ? I9 C27 C28 C29 -1.6(13) 2_666 . . 2_666 ? I8 C27 C28 C29 0.3(13) . . . 2_666 ? F8 C28 C29 F8 179.9(15) . . . 2_666 ? C27 C28 C29 F8 179(2) 2_666 . . 2_666 ? C27 C28 C29 F8 -0.4(7) . . . 2_666 ? C29 C28 C29 F8 41(100) 2_666 . . 2_666 ? F8 C28 C29 C30 -178.3(13) . . . . ? F8 C28 C29 C30 1.8(7) 2_666 . . . ? C27 C28 C29 C30 -179(2) 2_666 . . . ? C27 C28 C29 C30 1.4 . . . . ? C29 C28 C29 C30 43(100) 2_666 . . . ? F8 C28 C29 C27 0.4(11) . . . 2_666 ? F8 C28 C29 C27 -179(2) 2_666 . . 2_666 ? C27 C28 C29 C27 -180(2) . . . 2_666 ? C29 C28 C29 C27 -139(100) 2_666 . . 2_666 ? F8 C28 C29 I8 0.7(12) . . . 2_666 ? F8 C28 C29 I8 -179.2(14) 2_666 . . 2_666 ? C27 C28 C29 I8 0.3(14) 2_666 . . 2_666 ? C27 C28 C29 I8 -179.5(10) . . . 2_666 ? C29 C28 C29 I8 -138(100) 2_666 . . 2_666 ? F8 C28 C29 I9 -0.9(11) . . . . ? F8 C28 C29 I9 179.2(12) 2_666 . . . ? C27 C28 C29 I9 -1.3(14) 2_666 . . . ? C27 C28 C29 I9 178.9(8) . . . . ? C29 C28 C29 I9 -140(100) 2_666 . . . ? F8 C29 C30 F9 178.3(12) 2_666 . . . ? C27 C29 C30 F9 148(43) 2_666 . . . ? C28 C29 C30 F9 176.7(10) . . . . ? I8 C29 C30 F9 -2.7(10) 2_666 . . . ? I9 C29 C30 F9 -0.8(11) . . . . ? F8 C29 C30 C25 1.0(6) 2_666 . . . ? C27 C29 C30 C25 -30(43) 2_666 . . . ? C28 C29 C30 C25 -0.7 . . . . ? I8 C29 C30 C25 179.9(7) 2_666 . . . ? I9 C29 C30 C25 -178.1(8) . . . . ? C27 C29 C30 F8 -31(43) 2_666 . . 2_666 ? C28 C29 C30 F8 -1.7(6) . . . 2_666 ? I8 C29 C30 F8 179.0(10) 2_666 . . 2_666 ? I9 C29 C30 F8 -179.1(11) . . . 2_666 ? F8 C29 C30 I8 -179.0(10) 2_666 . . 2_666 ? C27 C29 C30 I8 150(43) 2_666 . . 2_666 ? C28 C29 C30 I8 179.4(7) . . . 2_666 ? I9 C29 C30 I8 1.9(2) . . . 2_666 ? C26 C25 C30 F9 -177.4(10) . . . . ? F8 C25 C30 F9 -178.3(12) 2_666 . . . ? I7 C25 C30 F9 -17(2) 2_566 . . . ? I7 C25 C30 F9 -0.2(10) . . . . ? C26 C25 C30 C29 0.0 . . . . ? F8 C25 C30 C29 -0.9(6) 2_666 . . . ? I7 C25 C30 C29 160(2) 2_566 . . . ? I7 C25 C30 C29 177.2(8) . . . . ? C26 C25 C30 F8 0.9(6) . . . 2_666 ? I7 C25 C30 F8 161(2) 2_566 . . 2_666 ? I7 C25 C30 F8 178.1(10) . . . 2_666 ? C26 C25 C30 I8 0(2) . . . 2_666 ? F8 C25 C30 I8 -1(2) 2_666 . . 2_666 ? I7 C25 C30 I8 160.4(18) 2_566 . . 2_666 ? I7 C25 C30 I8 177.4(19) . . . 2_666 ? C27 C26 F7 I7 173.1(7) . . . 2_566 ? C25 C26 F7 I7 -6.1(9) . . . 2_566 ? F8 C26 F7 I7 176(17) 2_666 . . 2_566 ? I9 C26 F7 I7 174.4(6) 2_666 . . 2_566 ? F8 C28 F8 C27 100(100) 2_666 . . 2_666 ? C27 C28 F8 C27 180(2) . . . 2_666 ? C29 C28 F8 C27 -0.4(11) . . . 2_666 ? C29 C28 F8 C27 179(3) 2_666 . . 2_666 ? F8 C28 F8 C29 -79(100) 2_666 . . 2_666 ? C27 C28 F8 C29 -179(3) 2_666 . . 2_666 ? C27 C28 F8 C29 0.4(11) . . . 2_666 ? C29 C28 F8 C29 -180(2) . . . 2_666 ? F8 C28 F8 C26 98(100) 2_666 . . 2_666 ? C27 C28 F8 C26 -1.8(7) 2_666 . . 2_666 ? C27 C28 F8 C26 178.1(19) . . . 2_666 ? C29 C28 F8 C26 -2.1(14) . . . 2_666 ? C29 C28 F8 C26 178(3) 2_666 . . 2_666 ? F8 C28 F8 C30 -78(100) 2_666 . . 2_666 ? C27 C28 F8 C30 -178(3) 2_666 . . 2_666 ? C27 C28 F8 C30 2.0(14) . . . 2_666 ? C29 C28 F8 C30 -178.2(18) . . . 2_666 ? C29 C28 F8 C30 1.6(6) 2_666 . . 2_666 ? F8 C28 F8 C25 -27(100) 2_666 . . 2_666 ? C27 C28 F8 C25 -127(26) 2_666 . . 2_666 ? C27 C28 F8 C25 52(27) . . . 2_666 ? C29 C28 F8 C25 -128(26) . . . 2_666 ? C29 C28 F8 C25 52(27) 2_666 . . 2_666 ? C26 C25 I7 I7 5.2(5) . . . 2_566 ? C30 C25 I7 I7 -172.0(6) . . . 2_566 ? F8 C25 I7 I7 -44(24) 2_666 . . 2_566 ? C26 C25 I7 F7 170.3(9) . . . 2_566 ? C30 C25 I7 F7 -6.9(12) . . . 2_566 ? F8 C25 I7 F7 121(24) 2_666 . . 2_566 ? I7 C25 I7 F7 165.1(9) 2_566 . . 2_566 ? C26 C25 I7 C25 5.2(5) . . . 2_566 ? C30 C25 I7 C25 -172.0(6) . . . 2_566 ? F8 C25 I7 C25 -44(24) 2_666 . . 2_566 ? I7 C25 I7 C25 0.0 2_566 . . 2_566 ? C26 C25 I7 C26 34(8) . . . 2_566 ? C30 C25 I7 C26 -144(8) . . . 2_566 ? F8 C25 I7 C26 -16(21) 2_666 . . 2_566 ? I7 C25 I7 C26 29(8) 2_566 . . 2_566 ? F8 C27 I8 I9 -172(32) 2_666 . . 2_666 ? C28 C27 I8 I9 -175.9(7) . . . 2_666 ? C26 C27 I8 I9 5.7(7) . . . 2_666 ? C29 C27 I8 I9 -175.6(17) 2_666 . . 2_666 ? F8 C27 I8 C29 4(31) 2_666 . . 2_666 ? C28 C27 I8 C29 -0.4(14) . . . 2_666 ? C26 C27 I8 C29 -179(2) . . . 2_666 ? I9 C27 I8 C29 175.6(17) 2_666 . . 2_666 ? F8 C27 I8 C30 3(31) 2_666 . . 2_666 ? C28 C27 I8 C30 -1.0(9) . . . 2_666 ? C26 C27 I8 C30 -179.4(15) . . . 2_666 ? C29 C27 I8 C30 -0.7(6) 2_666 . . 2_666 ? I9 C27 I8 C30 174.9(11) 2_666 . . 2_666 ? F8 C29 I9 I8 -174(13) 2_666 . . 2_666 ? C30 C29 I9 I8 -5.7(7) . . . 2_666 ? C27 C29 I9 I8 175.7(16) 2_666 . . 2_666 ? C28 C29 I9 I8 176.9(7) . . . 2_666 ? F8 C29 I9 C27 10(12) 2_666 . . 2_666 ? C30 C29 I9 C27 179(2) . . . 2_666 ? C28 C29 I9 C27 1.2(13) . . . 2_666 ? I8 C29 I9 C27 -175.7(16) 2_666 . . 2_666 ? F8 C29 I9 C26 10(13) 2_666 . . 2_666 ? C30 C29 I9 C26 179.3(15) . . . 2_666 ? C27 C29 I9 C26 0.7(6) 2_666 . . 2_666 ? C28 C29 I9 C26 1.9(9) . . . 2_666 ? I8 C29 I9 C26 -175.0(11) 2_666 . . 2_666 ? N2 C2 C3 C4 1.5(10) . . . . ? C9 C2 C3 C4 -179.2(7) . . . . ? C2 C3 C4 N1 -1.5(10) . . . . ? C2 C3 C4 C10 178.9(7) . . . . ? N1 C1 C5 N4 61.3(7) . . . . ? N2 C1 C5 N4 -118.4(6) . . . . ? N1 C1 C5 N3 -118.1(6) . . . . ? N2 C1 C5 N3 62.2(7) . . . . ? N4 C6 C7 C8 1.4(11) . . . . ? C11 C6 C7 C8 -179.4(8) . . . . ? C6 C7 C8 N3 -1.4(11) . . . . ? C6 C7 C8 C12 179.2(7) . . . . ? C18 C13 C14 F2 -177.9(5) . . . . ? I1 C13 C14 F2 0.9(8) . . . . ? C18 C13 C14 C15 -0.7(9) . . . . ? I1 C13 C14 C15 178.1(5) . . . . ? C13 C14 C15 C16 1.6(9) . . . . ? F2 C14 C15 C16 178.8(5) . . . . ? C13 C14 C15 I2 -177.7(5) . . . . ? F2 C14 C15 I2 -0.5(8) . . . . ? C14 C15 C16 F3 179.7(5) . . . . ? I2 C15 C16 F3 -0.9(8) . . . . ? C14 C15 C16 C17 -1.7(10) . . . . ? I2 C15 C16 C17 177.6(5) . . . . ? F3 C16 C17 C18 179.5(6) . . . . ? C15 C16 C17 C18 0.9(10) . . . . ? F3 C16 C17 I3 2.5(8) . . . . ? C15 C16 C17 I3 -176.1(5) . . . . ? C16 C17 C18 F1 -179.1(6) . . . . ? I3 C17 C18 F1 -2.1(8) . . . . ? C16 C17 C18 C13 0.1(10) . . . . ? I3 C17 C18 C13 177.2(5) . . . . ? C14 C13 C18 F1 179.0(6) . . . . ? I1 C13 C18 F1 0.2(8) . . . . ? C14 C13 C18 C17 -0.2(9) . . . . ? I1 C13 C18 C17 -179.1(5) . . . . ? C24 C19 C20 F5 -178.8(6) . . . . ? I4 C19 C20 F5 -0.7(9) . . . . ? C24 C19 C20 C21 1.1(10) . . . . ? I4 C19 C20 C21 179.2(5) . . . . ? F5 C20 C21 C22 179.0(6) . . . . ? C19 C20 C21 C22 -0.9(10) . . . . ? F5 C20 C21 I5 -1.5(8) . . . . ? C19 C20 C21 I5 178.5(5) . . . . ? C20 C21 C22 F6 -179.5(6) . . . . ? I5 C21 C22 F6 1.1(9) . . . . ? C20 C21 C22 C23 -0.1(10) . . . . ? I5 C21 C22 C23 -179.5(5) . . . . ? C21 C22 C23 C24 0.7(10) . . . . ? F6 C22 C23 C24 -179.9(6) . . . . ? C21 C22 C23 I6 -177.2(5) . . . . ? F6 C22 C23 I6 2.2(9) . . . . ? C20 C19 C24 F4 178.0(6) . . . . ? I4 C19 C24 F4 -0.1(9) . . . . ? C20 C19 C24 C23 -0.4(10) . . . . ? I4 C19 C24 C23 -178.5(5) . . . . ? C22 C23 C24 F4 -178.9(6) . . . . ? I6 C23 C24 F4 -0.9(8) . . . . ? C22 C23 C24 C19 -0.4(10) . . . . ? I6 C23 C24 C19 177.5(5) . . . . ? N2 C1 N1 C4 2.7(9) . . . . ? C5 C1 N1 C4 -177.0(5) . . . . ? C3 C4 N1 C1 -0.5(9) . . . . ? C10 C4 N1 C1 179.1(6) . . . . ? N1 C1 N2 C2 -2.6(9) . . . . ? C5 C1 N2 C2 177.0(5) . . . . ? C3 C2 N2 C1 0.4(9) . . . . ? C9 C2 N2 C1 -178.9(6) . . . . ? N4 C5 N3 C8 0.1(9) . . . . ? C1 C5 N3 C8 179.5(5) . . . . ? C7 C8 N3 C5 0.7(10) . . . . ? C12 C8 N3 C5 -179.9(6) . . . . ? N3 C5 N4 C6 -0.1(9) . . . . ? C1 C5 N4 C6 -179.5(6) . . . . ? C7 C6 N4 C5 -0.6(10) . . . . ? C11 C6 N4 C5 -179.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.058 _refine_diff_density_min -1.644 _refine_diff_density_rms 0.176 data_1a _database_code_depnum_ccdc_archive 'CCDC 908536' #TrackingRef 'WZW.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 F4 I2 N4' _chemical_formula_weight 616.13 _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' I I -0.4742 1.8119 '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 _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 7.5669(8) _cell_length_b 24.046(3) _cell_length_c 11.6567(15) _cell_angle_alpha 90.00 _cell_angle_beta 108.7840(10) _cell_angle_gamma 90.00 _cell_volume 2008.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6113 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 28.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.038 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 3.179 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3628 _exptl_absorpt_correction_T_max 0.5834 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14734 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3734 _reflns_number_gt 3112 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0189P)^2^+2.5463P] 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 3734 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0597 _refine_ls_wR_factor_gt 0.0562 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _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 F1 F 0.0895(4) 0.25766(10) 0.1984(2) 0.0747(7) Uani 1 1 d . . . F2 F -0.0511(4) 0.16092(12) 0.0898(2) 0.0892(9) Uani 1 1 d . . . F3 F 0.0223(4) 0.06484(10) 0.2149(2) 0.0793(8) Uani 1 1 d . . . F4 F 0.3700(3) 0.16207(8) 0.56262(19) 0.0644(6) Uani 1 1 d . . . I1 I 0.32695(4) 0.286322(10) 0.47482(2) 0.05971(10) Uani 1 1 d . . . I2 I 0.25882(4) 0.037641(10) 0.49158(3) 0.06021(10) Uani 1 1 d . . . N1 N 0.5950(4) 0.33966(11) 0.7370(3) 0.0454(7) Uani 1 1 d . . . N2 N 0.6773(4) 0.40885(11) 0.8919(2) 0.0408(6) Uani 1 1 d . . . N3 N 0.5144(4) 0.48723(11) 0.7203(2) 0.0425(7) Uani 1 1 d . . . N4 N 0.3629(4) 0.41415(11) 0.5861(2) 0.0436(7) Uani 1 1 d . . . C1 C 0.0560(6) 0.16099(17) 0.2073(3) 0.0566(10) Uani 1 1 d . . . C2 C 0.0929(5) 0.11242(16) 0.2720(3) 0.0526(9) Uani 1 1 d . . . C3 C 0.1999(5) 0.11132(13) 0.3924(3) 0.0430(8) Uani 1 1 d . . . C4 C 0.2672(5) 0.16175(13) 0.4447(3) 0.0422(8) Uani 1 1 d . . . C5 C 0.2331(5) 0.21194(13) 0.3841(3) 0.0436(8) Uani 1 1 d . . . C6 C 0.1273(5) 0.21001(15) 0.2631(3) 0.0508(9) Uani 1 1 d . . . C7 C 0.6867(5) 0.30119(14) 0.8173(3) 0.0471(9) Uani 1 1 d . . . C8 C 0.7740(5) 0.31548(15) 0.9364(3) 0.0495(9) Uani 1 1 d . . . H8 H 0.8365 0.2886 0.9922 0.059 Uiso 1 1 calc R . . C9 C 0.7681(5) 0.36960(15) 0.9725(3) 0.0441(8) Uani 1 1 d . . . C10 C 0.5938(4) 0.39138(13) 0.7782(3) 0.0376(7) Uani 1 1 d . . . C11 C 0.4835(5) 0.43385(13) 0.6884(3) 0.0381(7) Uani 1 1 d . . . C12 C 0.4123(5) 0.52473(14) 0.6414(3) 0.0449(8) Uani 1 1 d . . . C13 C 0.2836(5) 0.50808(15) 0.5342(3) 0.0494(9) Uani 1 1 d . . . H13 H 0.2129 0.5343 0.4799 0.059 Uiso 1 1 calc R . . C14 C 0.2604(5) 0.45223(15) 0.5081(3) 0.0467(9) Uani 1 1 d . . . C15 C 0.1194(6) 0.43175(17) 0.3933(4) 0.0670(12) Uani 1 1 d . . . H15A H 0.1828 0.4149 0.3428 0.100 Uiso 1 1 calc R . . H15B H 0.0457 0.4625 0.3511 0.100 Uiso 1 1 calc R . . H15C H 0.0396 0.4048 0.4125 0.100 Uiso 1 1 calc R . . C16 C 0.4422(6) 0.58519(14) 0.6747(4) 0.0629(11) Uani 1 1 d . . . H16A H 0.3554 0.5967 0.7146 0.094 Uiso 1 1 calc R . . H16B H 0.4229 0.6070 0.6026 0.094 Uiso 1 1 calc R . . H16C H 0.5674 0.5906 0.7280 0.094 Uiso 1 1 calc R . . C17 C 0.8593(6) 0.38750(17) 1.1010(3) 0.0641(12) Uani 1 1 d . . . H17A H 0.9643 0.4109 1.1059 0.096 Uiso 1 1 calc R . . H17B H 0.9009 0.3553 1.1512 0.096 Uiso 1 1 calc R . . H17C H 0.7712 0.4078 1.1285 0.096 Uiso 1 1 calc R . . C18 C 0.6875(7) 0.24247(15) 0.7735(4) 0.0685(12) Uani 1 1 d . . . H18A H 0.5698 0.2252 0.7658 0.103 Uiso 1 1 calc R . . H18B H 0.7860 0.2220 0.8307 0.103 Uiso 1 1 calc R . . H18C H 0.7071 0.2426 0.6962 0.103 Uiso 1 1 calc R . . _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 F1 0.0968(19) 0.0611(15) 0.0581(14) 0.0234(12) 0.0138(13) 0.0162(13) F2 0.094(2) 0.111(2) 0.0411(13) -0.0050(13) -0.0078(13) -0.0060(16) F3 0.0911(18) 0.0617(15) 0.0739(16) -0.0330(13) 0.0108(14) -0.0250(13) F4 0.0850(16) 0.0411(12) 0.0454(12) 0.0026(9) -0.0091(11) -0.0075(11) I1 0.0822(2) 0.03132(13) 0.06597(18) -0.00503(11) 0.02432(14) -0.00774(12) I2 0.06371(18) 0.03150(13) 0.0857(2) 0.00644(12) 0.02441(15) 0.00109(11) N1 0.0531(18) 0.0355(15) 0.0402(16) -0.0027(12) 0.0047(13) 0.0031(13) N2 0.0489(17) 0.0346(14) 0.0355(15) -0.0017(12) 0.0089(13) -0.0012(12) N3 0.0532(18) 0.0337(15) 0.0368(15) -0.0023(12) 0.0091(13) 0.0006(13) N4 0.0495(17) 0.0360(15) 0.0392(16) -0.0036(12) 0.0057(13) 0.0032(13) C1 0.055(2) 0.070(3) 0.035(2) -0.0067(18) 0.0010(17) 0.001(2) C2 0.051(2) 0.047(2) 0.055(2) -0.0162(18) 0.0109(18) -0.0069(18) C3 0.0438(19) 0.0325(17) 0.050(2) -0.0018(15) 0.0116(16) -0.0003(15) C4 0.047(2) 0.0324(17) 0.0401(19) -0.0001(14) 0.0033(15) 0.0001(14) C5 0.051(2) 0.0335(17) 0.0429(19) -0.0010(15) 0.0107(16) 0.0001(15) C6 0.058(2) 0.046(2) 0.044(2) 0.0076(17) 0.0106(18) 0.0104(18) C7 0.051(2) 0.0349(18) 0.050(2) -0.0001(16) 0.0077(17) 0.0026(15) C8 0.057(2) 0.0392(19) 0.045(2) 0.0075(16) 0.0055(17) 0.0038(17) C9 0.047(2) 0.045(2) 0.0373(18) 0.0042(15) 0.0086(16) -0.0021(16) C10 0.0408(18) 0.0338(17) 0.0355(18) -0.0015(14) 0.0084(14) -0.0006(14) C11 0.0452(19) 0.0343(17) 0.0341(17) -0.0014(14) 0.0115(15) 0.0028(14) C12 0.058(2) 0.0349(18) 0.044(2) 0.0028(15) 0.0185(17) 0.0055(16) C13 0.060(2) 0.044(2) 0.0393(19) 0.0042(16) 0.0087(17) 0.0146(17) C14 0.051(2) 0.045(2) 0.0382(19) -0.0025(15) 0.0074(16) 0.0079(16) C15 0.070(3) 0.056(2) 0.052(2) -0.0041(19) -0.012(2) 0.017(2) C16 0.090(3) 0.0319(19) 0.063(3) -0.0020(17) 0.019(2) 0.0056(19) C17 0.090(3) 0.053(2) 0.037(2) 0.0000(18) 0.002(2) -0.002(2) C18 0.087(3) 0.034(2) 0.069(3) -0.0042(19) 0.003(2) 0.012(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. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C6 1.350(4) . ? F2 C1 1.348(4) . ? F3 C2 1.345(4) . ? F4 C4 1.343(4) . ? I1 C5 2.083(3) . ? I2 C3 2.084(3) . ? N1 C10 1.334(4) . ? N1 C7 1.339(4) . ? N2 C10 1.339(4) . ? N2 C9 1.353(4) . ? N3 C11 1.336(4) . ? N3 C12 1.342(4) . ? N4 C11 1.334(4) . ? N4 C14 1.346(4) . ? C1 C2 1.369(5) . ? C1 C6 1.370(5) . ? C2 C3 1.376(5) . ? C3 C4 1.379(4) . ? C4 C5 1.381(4) . ? C5 C6 1.380(5) . ? C7 C8 1.376(5) . ? C7 C18 1.502(5) . ? C8 C9 1.373(5) . ? C8 H8 0.9300 . ? C9 C17 1.497(5) . ? C10 C11 1.508(4) . ? C12 C13 1.373(5) . ? C12 C16 1.503(5) . ? C13 C14 1.376(5) . ? C13 H13 0.9300 . ? C14 C15 1.501(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? _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 C10 N1 C7 117.0(3) . . ? C10 N2 C9 116.2(3) . . ? C11 N3 C12 116.4(3) . . ? C11 N4 C14 116.2(3) . . ? F2 C1 C2 120.5(4) . . ? F2 C1 C6 119.9(4) . . ? C2 C1 C6 119.5(3) . . ? F3 C2 C1 118.4(3) . . ? F3 C2 C3 119.8(3) . . ? C1 C2 C3 121.8(3) . . ? C2 C3 C4 116.5(3) . . ? C2 C3 I2 122.2(3) . . ? C4 C3 I2 121.3(3) . . ? F4 C4 C3 117.9(3) . . ? F4 C4 C5 118.0(3) . . ? C3 C4 C5 124.1(3) . . ? C6 C5 C4 116.4(3) . . ? C6 C5 I1 122.6(3) . . ? C4 C5 I1 120.9(2) . . ? F1 C6 C1 119.0(3) . . ? F1 C6 C5 119.4(3) . . ? C1 C6 C5 121.6(3) . . ? N1 C7 C8 120.3(3) . . ? N1 C7 C18 118.0(3) . . ? C8 C7 C18 121.6(3) . . ? C9 C8 C7 119.6(3) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? N2 C9 C8 120.5(3) . . ? N2 C9 C17 117.5(3) . . ? C8 C9 C17 121.9(3) . . ? N1 C10 N2 126.4(3) . . ? N1 C10 C11 116.6(3) . . ? N2 C10 C11 117.0(3) . . ? N4 C11 N3 126.8(3) . . ? N4 C11 C10 116.5(3) . . ? N3 C11 C10 116.7(3) . . ? N3 C12 C13 120.8(3) . . ? N3 C12 C16 117.9(3) . . ? C13 C12 C16 121.4(3) . . ? C12 C13 C14 119.2(3) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? N4 C14 C13 120.7(3) . . ? N4 C14 C15 117.9(3) . . ? C13 C14 C15 121.4(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C17 H17A 109.5 . . ? C9 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C9 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C7 C18 H18A 109.5 . . ? C7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _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 F2 C1 C2 F3 1.1(6) . . . . ? C6 C1 C2 F3 -179.6(4) . . . . ? F2 C1 C2 C3 -179.2(4) . . . . ? C6 C1 C2 C3 0.1(6) . . . . ? F3 C2 C3 C4 -180.0(3) . . . . ? C1 C2 C3 C4 0.4(6) . . . . ? F3 C2 C3 I2 0.1(5) . . . . ? C1 C2 C3 I2 -179.5(3) . . . . ? C2 C3 C4 F4 179.1(3) . . . . ? I2 C3 C4 F4 -1.0(5) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? I2 C3 C4 C5 -180.0(3) . . . . ? F4 C4 C5 C6 179.9(3) . . . . ? C3 C4 C5 C6 -1.1(6) . . . . ? F4 C4 C5 I1 -3.0(5) . . . . ? C3 C4 C5 I1 175.9(3) . . . . ? F2 C1 C6 F1 -0.4(6) . . . . ? C2 C1 C6 F1 -179.8(4) . . . . ? F2 C1 C6 C5 178.2(4) . . . . ? C2 C1 C6 C5 -1.2(6) . . . . ? C4 C5 C6 F1 -179.8(3) . . . . ? I1 C5 C6 F1 3.2(5) . . . . ? C4 C5 C6 C1 1.7(6) . . . . ? I1 C5 C6 C1 -175.3(3) . . . . ? C10 N1 C7 C8 0.2(5) . . . . ? C10 N1 C7 C18 179.0(4) . . . . ? N1 C7 C8 C9 -0.6(6) . . . . ? C18 C7 C8 C9 -179.4(4) . . . . ? C10 N2 C9 C8 0.9(5) . . . . ? C10 N2 C9 C17 -178.6(3) . . . . ? C7 C8 C9 N2 0.0(6) . . . . ? C7 C8 C9 C17 179.5(4) . . . . ? C7 N1 C10 N2 0.9(5) . . . . ? C7 N1 C10 C11 -177.5(3) . . . . ? C9 N2 C10 N1 -1.4(5) . . . . ? C9 N2 C10 C11 176.9(3) . . . . ? C14 N4 C11 N3 -1.0(5) . . . . ? C14 N4 C11 C10 177.9(3) . . . . ? C12 N3 C11 N4 0.6(5) . . . . ? C12 N3 C11 C10 -178.3(3) . . . . ? N1 C10 C11 N4 15.4(5) . . . . ? N2 C10 C11 N4 -163.1(3) . . . . ? N1 C10 C11 N3 -165.6(3) . . . . ? N2 C10 C11 N3 15.9(5) . . . . ? C11 N3 C12 C13 0.1(5) . . . . ? C11 N3 C12 C16 179.5(3) . . . . ? N3 C12 C13 C14 -0.2(6) . . . . ? C16 C12 C13 C14 -179.6(4) . . . . ? C11 N4 C14 C13 0.8(5) . . . . ? C11 N4 C14 C15 -178.4(3) . . . . ? C12 C13 C14 N4 -0.3(6) . . . . ? C12 C13 C14 C15 178.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.823 _refine_diff_density_min -0.948 _refine_diff_density_rms 0.075