data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Six, Yvan' _publ_contact_author_name 'Six, Yvan' _publ_contact_author_email yvan.six@icsn.cnrs-gif.fr _publ_section_title ; Aminocyclopropanes as precursors of endoperoxides with antimalarial activity ; # Attachment '- cmpd_3g_final.cif' # Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_(R*,R*)-3g _database_code_depnum_ccdc_archive 'CCDC 782249' #TrackingRef '- cmpd_3g_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-(2S,7S,E)-1,1,1,8,8,8-hexafluorooct-4-ene-2,7-diyl)bis(N-(4- methoxylphenyl)acetamide) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H28 F6 N2 O4' _chemical_formula_sum 'C26 H28 F6 N2 O4' _chemical_formula_weight 546.50 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0171 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.001(2) _cell_length_b 11.945(2) _cell_length_c 20.385(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2678.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11494 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 20.816 _exptl_crystal_description 'thin stick' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19854 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _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 1.98 _diffrn_reflns_theta_max 20.80 _reflns_number_total 1614 _reflns_number_gt 1447 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)' _computing_data_reduction 'HKL package (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1980-2004)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The crystals were very weakly diffracting and very little data was obtainable beyond \q = 21/% using a molybdenum radiation source at room temperature. However, the results of X-ray analysis looked reasonable from chemical/crystallographical point of view. The crystal although it belongs to a Sohnke space group, P 21 21 21, is made of a racemate. ; _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^)+(0.0709P)^2^+0.1856P] 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 0.0077(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1614 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.4329(4) 0.0003(2) 1.17831(12) 0.0999(11) Uani 1 1 d . . . F2 F 0.4388(3) -0.1389(2) 1.11253(14) 0.1011(11) Uani 1 1 d . . . F3 F 0.2743(3) -0.0462(3) 1.12374(14) 0.0953(10) Uani 1 1 d . . . F4 F 0.3242(4) 0.6262(2) 0.89907(18) 0.1172(12) Uani 1 1 d . . . F5 F 0.4871(4) 0.5633(2) 0.85668(17) 0.1056(11) Uani 1 1 d . . . F6 F 0.3209(4) 0.5508(3) 0.80330(17) 0.1255(14) Uani 1 1 d . . . O1 O 0.6309(3) -0.0138(3) 0.99043(16) 0.0822(10) Uani 1 1 d . . . O2 O -0.0277(3) -0.1156(3) 0.8952(2) 0.0902(11) Uani 1 1 d . . . O3 O 0.1553(3) 0.3068(4) 0.84396(19) 0.0979(12) Uani 1 1 d . . . O4 O 0.8270(3) 0.2015(3) 0.78182(15) 0.0707(9) Uani 1 1 d . . . N1 N 0.4260(3) -0.0105(3) 1.00167(15) 0.0486(9) Uani 1 1 d . . . N2 N 0.3580(3) 0.3383(3) 0.84692(15) 0.0538(9) Uani 1 1 d . . . C1 C 0.3951(6) -0.0360(4) 1.1197(2) 0.0706(14) Uani 1 1 d . . . C2 C 0.4373(4) 0.0424(3) 1.06600(17) 0.0523(11) Uani 1 1 d . . . H2 H 0.5242 0.0555 1.0733 0.063 Uiso 1 1 calc R . . C3 C 0.3740(4) 0.1561(3) 1.07258(19) 0.0547(11) Uani 1 1 d . . . H3A H 0.2884 0.1470 1.0625 0.066 Uiso 1 1 calc R . . H3B H 0.3802 0.1810 1.1177 0.066 Uiso 1 1 calc R . . C4 C 0.4257(4) 0.2441(3) 1.02892(18) 0.0539(11) Uani 1 1 d . . . H4 H 0.5096 0.2456 1.0234 0.065 Uiso 1 1 calc R . . C5 C 0.3609(4) 0.3201(3) 0.99766(18) 0.0533(11) Uani 1 1 d . . . H5 H 0.2769 0.3136 1.0007 0.064 Uiso 1 1 calc R . . C6 C 0.4083(4) 0.4151(3) 0.9579(2) 0.0589(12) Uani 1 1 d . . . H6A H 0.4936 0.4023 0.9486 0.071 Uiso 1 1 calc R . . H6B H 0.4022 0.4834 0.9835 0.071 Uiso 1 1 calc R . . C7 C 0.3414(4) 0.4311(3) 0.8943(2) 0.0557(11) Uani 1 1 d . . . H7 H 0.2547 0.4325 0.9052 0.067 Uiso 1 1 calc R . . C8 C 0.3694(6) 0.5419(4) 0.8629(3) 0.0811(15) Uani 1 1 d . . . C9 C 0.5309(5) -0.0375(3) 0.9688(2) 0.0566(11) Uani 1 1 d . . . C10 C 0.5181(4) -0.0960(4) 0.9041(2) 0.0777(15) Uani 1 1 d . . . H10A H 0.4769 -0.1660 0.9104 0.117 Uiso 1 1 calc R . . H10B H 0.5972 -0.1096 0.8859 0.117 Uiso 1 1 calc R . . H10C H 0.4720 -0.0500 0.8746 0.117 Uiso 1 1 calc R . . C11 C 0.3077(4) -0.0350(3) 0.97494(18) 0.0478(11) Uani 1 1 d . . . C12 C 0.2554(4) -0.1408(4) 0.9831(2) 0.0616(12) Uani 1 1 d . . . H12 H 0.2956 -0.1954 1.0073 0.074 Uiso 1 1 calc R . . C13 C 0.1441(5) -0.1638(4) 0.9550(2) 0.0690(13) Uani 1 1 d . . . H13 H 0.1102 -0.2346 0.9601 0.083 Uiso 1 1 calc R . . C14 C 0.0820(4) -0.0837(4) 0.9195(2) 0.0623(12) Uani 1 1 d . . . C15 C 0.1322(4) 0.0210(4) 0.9121(2) 0.0601(12) Uani 1 1 d . . . H15 H 0.0909 0.0759 0.8887 0.072 Uiso 1 1 calc R . . C16 C 0.2444(4) 0.0440(4) 0.93944(19) 0.0541(11) Uani 1 1 d . . . H16 H 0.2781 0.1148 0.9338 0.065 Uiso 1 1 calc R . . C17 C -0.0930(5) -0.0372(5) 0.8567(3) 0.1019(19) Uani 1 1 d . . . H17A H -0.0433 -0.0130 0.8207 0.153 Uiso 1 1 calc R . . H17B H -0.1142 0.0262 0.8833 0.153 Uiso 1 1 calc R . . H17C H -0.1656 -0.0716 0.8402 0.153 Uiso 1 1 calc R . . C18 C 0.2556(5) 0.2845(4) 0.8243(2) 0.0699(14) Uani 1 1 d . . . C19 C 0.2762(5) 0.1952(6) 0.7735(3) 0.0949(18) Uani 1 1 d . . . H19A H 0.2002 0.1601 0.7630 0.142 Uiso 1 1 calc R . . H19B H 0.3315 0.1402 0.7904 0.142 Uiso 1 1 calc R . . H19C H 0.3100 0.2284 0.7347 0.142 Uiso 1 1 calc R . . C20 C 0.4784(4) 0.3052(4) 0.8280(2) 0.0515(11) Uani 1 1 d . . . C21 C 0.5368(4) 0.2200(3) 0.86222(19) 0.0524(11) Uani 1 1 d . . . H21 H 0.4974 0.1846 0.8969 0.063 Uiso 1 1 calc R . . C22 C 0.6520(4) 0.1879(4) 0.84515(19) 0.0554(11) Uani 1 1 d . . . H22 H 0.6903 0.1314 0.8688 0.066 Uiso 1 1 calc R . . C23 C 0.7120(4) 0.2377(4) 0.7937(2) 0.0554(11) Uani 1 1 d . . . C24 C 0.6550(4) 0.3225(4) 0.7590(2) 0.0663(13) Uani 1 1 d . . . H24 H 0.6949 0.3578 0.7245 0.080 Uiso 1 1 calc R . . C25 C 0.5385(4) 0.3541(4) 0.7762(2) 0.0662(13) Uani 1 1 d . . . H25 H 0.4997 0.4097 0.7521 0.079 Uiso 1 1 calc R . . C26 C 0.8951(4) 0.2523(4) 0.7300(2) 0.0860(16) Uani 1 1 d . . . H26A H 0.8982 0.3318 0.7367 0.129 Uiso 1 1 calc R . . H26B H 0.8566 0.2367 0.6887 0.129 Uiso 1 1 calc R . . H26C H 0.9762 0.2226 0.7298 0.129 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.169(3) 0.0836(19) 0.0470(15) 0.0060(14) -0.0151(17) 0.005(2) F2 0.168(3) 0.0569(17) 0.0783(18) 0.0121(15) -0.014(2) 0.025(2) F3 0.113(3) 0.094(2) 0.079(2) 0.0225(18) 0.0220(18) -0.012(2) F4 0.160(3) 0.0545(17) 0.138(3) 0.0111(19) 0.036(3) 0.031(2) F5 0.114(3) 0.0672(19) 0.136(3) 0.0207(18) 0.032(2) -0.0096(19) F6 0.173(4) 0.104(2) 0.100(2) 0.047(2) -0.012(2) 0.033(3) O1 0.052(2) 0.109(3) 0.085(2) -0.025(2) -0.0042(18) 0.000(2) O2 0.062(2) 0.075(2) 0.133(3) -0.024(2) -0.021(2) -0.002(2) O3 0.053(2) 0.127(3) 0.113(3) -0.023(3) 0.001(2) 0.003(2) O4 0.053(2) 0.093(2) 0.0660(19) -0.0167(18) 0.0087(16) 0.0061(18) N1 0.051(2) 0.0484(19) 0.0460(18) -0.0061(16) -0.0019(18) 0.0024(17) N2 0.048(2) 0.063(2) 0.0502(19) 0.0012(17) -0.0058(18) 0.0059(19) C1 0.100(4) 0.062(3) 0.050(3) 0.000(3) -0.006(3) 0.017(3) C2 0.060(3) 0.054(2) 0.042(2) -0.002(2) -0.005(2) 0.008(2) C3 0.072(3) 0.049(3) 0.043(2) -0.0004(19) 0.004(2) 0.007(2) C4 0.065(3) 0.047(2) 0.049(2) -0.008(2) -0.003(2) 0.000(2) C5 0.063(3) 0.048(2) 0.049(2) -0.005(2) 0.002(2) 0.004(2) C6 0.073(3) 0.044(2) 0.060(3) -0.004(2) -0.002(2) 0.003(2) C7 0.058(3) 0.049(3) 0.060(3) 0.007(2) 0.007(2) 0.008(2) C8 0.093(4) 0.062(3) 0.088(4) 0.011(3) 0.009(3) 0.020(3) C9 0.061(3) 0.051(3) 0.058(3) -0.006(2) 0.006(3) 0.006(2) C10 0.073(3) 0.088(4) 0.073(3) -0.024(3) 0.008(3) 0.002(3) C11 0.050(3) 0.047(3) 0.047(2) -0.006(2) 0.002(2) 0.001(2) C12 0.075(3) 0.042(3) 0.068(3) 0.002(2) -0.009(3) 0.001(2) C13 0.067(3) 0.049(3) 0.091(3) -0.002(3) -0.003(3) -0.015(3) C14 0.051(3) 0.059(3) 0.077(3) -0.019(3) -0.002(3) 0.003(3) C15 0.056(3) 0.051(3) 0.074(3) -0.004(2) -0.011(2) 0.012(2) C16 0.057(3) 0.044(2) 0.061(3) -0.002(2) -0.001(2) -0.002(2) C17 0.065(4) 0.101(4) 0.140(5) -0.031(4) -0.031(4) 0.020(3) C18 0.062(4) 0.084(4) 0.065(3) 0.001(3) -0.007(3) 0.007(3) C19 0.077(4) 0.124(5) 0.083(4) -0.029(4) -0.016(3) -0.010(4) C20 0.048(3) 0.059(3) 0.048(2) -0.003(2) -0.001(2) 0.003(2) C21 0.054(3) 0.051(2) 0.051(2) 0.004(2) 0.002(2) 0.003(2) C22 0.055(3) 0.059(3) 0.052(2) 0.000(2) 0.000(2) 0.010(2) C23 0.054(3) 0.066(3) 0.046(2) -0.014(2) 0.000(2) -0.001(3) C24 0.069(3) 0.077(3) 0.052(3) 0.005(2) 0.014(3) -0.007(3) C25 0.072(3) 0.073(3) 0.053(3) 0.014(2) 0.000(3) 0.007(3) C26 0.066(3) 0.115(4) 0.078(3) -0.024(3) 0.027(3) -0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.337(5) . ? F2 C1 1.328(5) . ? F3 C1 1.337(6) . ? F4 C8 1.342(6) . ? F5 C8 1.326(7) . ? F6 C8 1.332(6) . ? O1 C9 1.218(5) . ? O2 C14 1.360(5) . ? O2 C17 1.417(6) . ? O3 C18 1.204(6) . ? O4 C23 1.360(5) . ? O4 C26 1.430(6) . ? N1 C9 1.374(5) . ? N1 C11 1.441(5) . ? N1 C2 1.461(5) . ? N2 C18 1.377(6) . ? N2 C20 1.435(5) . ? N2 C7 1.481(5) . ? C1 C2 1.514(7) . ? C2 C3 1.533(5) . ? C2 H2 0.9800 . ? C3 C4 1.490(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.318(5) . ? C4 H4 0.9300 . ? C5 C6 1.489(6) . ? C5 H5 0.9300 . ? C6 C7 1.503(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.502(7) . ? C7 H7 0.9800 . ? C9 C10 1.499(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.378(5) . ? C11 C12 1.398(6) . ? C12 C13 1.379(6) . ? C12 H12 0.9300 . ? C13 C14 1.380(6) . ? C13 H13 0.9300 . ? C14 C15 1.376(6) . ? C15 C16 1.382(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.503(7) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C25 1.376(6) . ? C20 C21 1.391(5) . ? C21 C22 1.368(6) . ? C21 H21 0.9300 . ? C22 C23 1.374(6) . ? C22 H22 0.9300 . ? C23 C24 1.385(6) . ? C24 C25 1.381(6) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O2 C17 117.8(4) . . ? C23 O4 C26 119.0(4) . . ? C9 N1 C11 121.8(3) . . ? C9 N1 C2 117.9(3) . . ? C11 N1 C2 120.3(3) . . ? C18 N2 C20 122.4(3) . . ? C18 N2 C7 117.9(3) . . ? C20 N2 C7 119.7(3) . . ? F2 C1 F1 106.7(4) . . ? F2 C1 F3 106.4(5) . . ? F1 C1 F3 106.5(4) . . ? F2 C1 C2 112.4(4) . . ? F1 C1 C2 110.5(4) . . ? F3 C1 C2 113.9(4) . . ? N1 C2 C1 110.9(3) . . ? N1 C2 C3 115.0(3) . . ? C1 C2 C3 110.2(3) . . ? N1 C2 H2 106.8 . . ? C1 C2 H2 106.8 . . ? C3 C2 H2 106.8 . . ? C4 C3 C2 113.6(3) . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 124.6(4) . . ? C5 C4 H4 117.7 . . ? C3 C4 H4 117.7 . . ? C4 C5 C6 126.8(4) . . ? C4 C5 H5 116.6 . . ? C6 C5 H5 116.6 . . ? C5 C6 C7 113.3(4) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N2 C7 C8 110.9(3) . . ? N2 C7 C6 114.0(3) . . ? C8 C7 C6 112.3(4) . . ? N2 C7 H7 106.3 . . ? C8 C7 H7 106.3 . . ? C6 C7 H7 106.3 . . ? F5 C8 F6 106.7(5) . . ? F5 C8 F4 105.7(5) . . ? F6 C8 F4 107.0(4) . . ? F5 C8 C7 114.2(4) . . ? F6 C8 C7 112.1(5) . . ? F4 C8 C7 110.6(4) . . ? O1 C9 N1 121.8(4) . . ? O1 C9 C10 120.8(4) . . ? N1 C9 C10 117.4(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 118.3(4) . . ? C16 C11 N1 121.0(4) . . ? C12 C11 N1 120.7(4) . . ? C13 C12 C11 119.7(4) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 121.3(4) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? O2 C14 C15 124.8(4) . . ? O2 C14 C13 115.9(4) . . ? C15 C14 C13 119.3(4) . . ? C14 C15 C16 119.7(4) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C11 C16 C15 121.8(4) . . ? C11 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? O2 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O3 C18 N2 122.3(4) . . ? O3 C18 C19 121.6(5) . . ? N2 C18 C19 116.1(4) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 118.2(4) . . ? C25 C20 N2 122.2(4) . . ? C21 C20 N2 119.6(4) . . ? C22 C21 C20 120.3(4) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 121.1(4) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? O4 C23 C22 116.4(4) . . ? O4 C23 C24 124.2(4) . . ? C22 C23 C24 119.3(4) . . ? C25 C24 C23 119.3(4) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C20 C25 C24 121.6(4) . . ? C20 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? O4 C26 H26A 109.5 . . ? O4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C2 C1 -111.3(4) . . . . ? C11 N1 C2 C1 67.5(5) . . . . ? C9 N1 C2 C3 122.9(4) . . . . ? C11 N1 C2 C3 -58.3(5) . . . . ? F2 C1 C2 N1 45.6(6) . . . . ? F1 C1 C2 N1 164.7(4) . . . . ? F3 C1 C2 N1 -75.5(5) . . . . ? F2 C1 C2 C3 174.1(4) . . . . ? F1 C1 C2 C3 -66.8(5) . . . . ? F3 C1 C2 C3 53.0(5) . . . . ? N1 C2 C3 C4 -63.7(5) . . . . ? C1 C2 C3 C4 170.1(4) . . . . ? C2 C3 C4 C5 141.0(4) . . . . ? C3 C4 C5 C6 174.7(3) . . . . ? C4 C5 C6 C7 136.4(4) . . . . ? C18 N2 C7 C8 -109.0(5) . . . . ? C20 N2 C7 C8 73.0(5) . . . . ? C18 N2 C7 C6 123.0(4) . . . . ? C20 N2 C7 C6 -54.9(5) . . . . ? C5 C6 C7 N2 -66.5(5) . . . . ? C5 C6 C7 C8 166.2(4) . . . . ? N2 C7 C8 F5 -77.4(6) . . . . ? C6 C7 C8 F5 51.5(6) . . . . ? N2 C7 C8 F6 44.2(6) . . . . ? C6 C7 C8 F6 173.1(4) . . . . ? N2 C7 C8 F4 163.5(4) . . . . ? C6 C7 C8 F4 -67.6(6) . . . . ? C11 N1 C9 O1 177.8(4) . . . . ? C2 N1 C9 O1 -3.4(6) . . . . ? C11 N1 C9 C10 -1.3(6) . . . . ? C2 N1 C9 C10 177.5(4) . . . . ? C9 N1 C11 C16 -94.5(5) . . . . ? C2 N1 C11 C16 86.8(4) . . . . ? C9 N1 C11 C12 84.0(5) . . . . ? C2 N1 C11 C12 -94.8(4) . . . . ? C16 C11 C12 C13 0.9(6) . . . . ? N1 C11 C12 C13 -177.6(4) . . . . ? C11 C12 C13 C14 -0.8(7) . . . . ? C17 O2 C14 C15 3.0(7) . . . . ? C17 O2 C14 C13 -178.1(5) . . . . ? C12 C13 C14 O2 -179.0(4) . . . . ? C12 C13 C14 C15 0.0(7) . . . . ? O2 C14 C15 C16 179.6(4) . . . . ? C13 C14 C15 C16 0.7(6) . . . . ? C12 C11 C16 C15 -0.1(6) . . . . ? N1 C11 C16 C15 178.3(3) . . . . ? C14 C15 C16 C11 -0.7(6) . . . . ? C20 N2 C18 O3 174.2(5) . . . . ? C7 N2 C18 O3 -3.6(6) . . . . ? C20 N2 C18 C19 -5.4(6) . . . . ? C7 N2 C18 C19 176.7(4) . . . . ? C18 N2 C20 C25 93.9(5) . . . . ? C7 N2 C20 C25 -88.3(5) . . . . ? C18 N2 C20 C21 -85.3(5) . . . . ? C7 N2 C20 C21 92.5(5) . . . . ? C25 C20 C21 C22 1.3(6) . . . . ? N2 C20 C21 C22 -179.5(4) . . . . ? C20 C21 C22 C23 -0.7(6) . . . . ? C26 O4 C23 C22 -178.4(4) . . . . ? C26 O4 C23 C24 -0.5(6) . . . . ? C21 C22 C23 O4 178.5(4) . . . . ? C21 C22 C23 C24 0.5(6) . . . . ? O4 C23 C24 C25 -178.8(4) . . . . ? C22 C23 C24 C25 -0.9(6) . . . . ? C21 C20 C25 C24 -1.7(6) . . . . ? N2 C20 C25 C24 179.1(4) . . . . ? C23 C24 C25 C20 1.5(7) . . . . ? _diffrn_measured_fraction_theta_max .998 _diffrn_reflns_theta_full 20.80 _diffrn_measured_fraction_theta_full .998 _refine_diff_density_max .126 _refine_diff_density_min -.130 _refine_diff_density_rms .030