# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _publ_contact_author_email KATHARINA.REICHENBAECHER@IAC.UNIBE.CH _publ_contact_author_name 'Ms Katharina Reichenbacher' _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_address ; Department of Chemistry and Biochemistry University Berne Freistrasse 3 Berne 3012 SWITZERLAND ; _publ_section_title ; Modification of channel structures by fluorination ; loop_ _publ_author_name 'Katharina Reichenbacher' 'Silvia Bracco' 'Jurg Hulliger' 'Piero Sozzani' ; H.Stoeckli-Evans ; 'Heike Suss' 'Edwin Weber' data_brtriaz _database_code_depnum_ccdc_archive 'CCDC 198640' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H12 Br3 N3 O3' _chemical_formula_sum 'C21 H12 Br3 N3 O3' _chemical_formula_weight 594.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting rhombohedral _symmetry_space_group_name_H-M 'R 3 c' _symmetry_space_group_name_Hall 'R 3 -2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-y, -x, z+1/2' '-x+y, -x, z' 'x, x-y, z+1/2' '-x+y, y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, -x+1/3, z+1/3' 'x+2/3, x-y+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, -x+2/3, z+2/3' 'x+1/3, x-y+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' _cell_length_a 23.869(2) _cell_length_b 23.869(2) _cell_length_c 6.4684(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3191.5(5) _cell_formula_units_Z 6 _cell_measurement_temperature 253(2) _cell_measurement_reflns_used 3252 _cell_measurement_theta_min 1.71 _cell_measurement_theta_max 24.01 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.855 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 5.716 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.244 _exptl_absorpt_correction_T_max 0.703 _exptl_absorpt_process_details DIFABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 253(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.87\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4839 _diffrn_reflns_av_R_equivalents 0.0925 _diffrn_reflns_av_sigmaI/netI 0.0815 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 24.01 _reflns_number_total 1090 _reflns_number_gt 843 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _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. ; _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^)+(0.0172P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(19) _refine_ls_number_reflns 1090 _refine_ls_number_parameters 91 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0595 _refine_ls_wR_factor_gt 0.0560 _refine_ls_goodness_of_fit_ref 0.900 _refine_ls_restrained_S_all 0.899 _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 Br1 Br -0.37123(3) -0.25125(4) -0.10153(16) 0.0526(2) Uani 1 1 d . . . O1 O -0.08073(16) -0.12452(18) -0.0740(7) 0.0285(10) Uani 1 1 d . . . N1 N -0.06549(19) -0.0213(2) -0.0684(7) 0.0206(11) Uani 1 1 d . . . C1 C -0.0415(3) -0.0601(3) -0.0680(9) 0.0198(13) Uani 1 1 d . . . C2 C -0.1487(2) -0.1505(2) -0.0808(10) 0.0248(14) Uani 1 1 d . . . C3 C -0.1811(3) -0.1436(3) 0.0842(10) 0.0281(15) Uani 1 1 d . . . H3A H -0.1583 -0.1188 0.1979 0.034 Uiso 1 1 calc R . . C4 C -0.2478(3) -0.1737(3) 0.0796(11) 0.0301(15) Uani 1 1 d . . . H4A H -0.2705 -0.1694 0.1892 0.036 Uiso 1 1 calc R . . C5 C -0.2803(2) -0.2109(3) -0.0929(10) 0.0288(15) Uani 1 1 d . . . C6 C -0.2473(3) -0.2181(3) -0.2524(10) 0.0336(17) Uani 1 1 d . . . H6A H -0.2698 -0.2439 -0.3647 0.040 Uiso 1 1 calc R . . C7 C -0.1802(3) -0.1871(3) -0.2488(10) 0.0306(16) Uani 1 1 d . . . H7A H -0.1573 -0.1914 -0.3583 0.037 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 Br1 0.0259(3) 0.0616(5) 0.0523(4) -0.0047(4) -0.0042(4) 0.0083(4) O1 0.023(2) 0.021(2) 0.039(3) -0.0044(19) -0.005(2) 0.0090(18) N1 0.022(2) 0.026(3) 0.012(3) 0.004(2) 0.002(2) 0.011(2) C1 0.025(3) 0.025(3) 0.006(4) -0.002(3) -0.002(3) 0.011(3) C2 0.022(3) 0.020(3) 0.028(4) 0.005(3) 0.000(3) 0.007(3) C3 0.031(3) 0.024(3) 0.020(4) -0.004(3) -0.007(3) 0.007(3) C4 0.033(3) 0.028(3) 0.028(5) -0.001(3) 0.000(3) 0.015(3) C5 0.023(3) 0.033(3) 0.026(4) 0.005(3) 0.000(3) 0.010(3) C6 0.031(3) 0.034(3) 0.023(5) -0.001(3) -0.015(3) 0.007(3) C7 0.032(3) 0.028(3) 0.027(5) -0.001(3) 0.004(3) 0.011(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 Br1 C5 1.884(5) . ? O1 C1 1.344(6) . ? O1 C2 1.419(6) . ? N1 C1 1.309(7) . ? N1 C1 1.350(6) 4 ? C1 N1 1.350(6) 2 ? C2 C7 1.361(9) . ? C2 C3 1.375(8) . ? C3 C4 1.381(8) . ? C3 H3A 0.9300 . ? C4 C5 1.395(9) . ? C4 H4A 0.9300 . ? C5 C6 1.360(8) . ? C6 C7 1.389(7) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? 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 C1 O1 C2 119.4(4) . . ? C1 N1 C1 111.8(5) . 4 ? N1 C1 O1 120.5(5) . . ? N1 C1 N1 128.2(5) . 2 ? O1 C1 N1 111.2(4) . 2 ? C7 C2 C3 122.3(5) . . ? C7 C2 O1 116.6(5) . . ? C3 C2 O1 120.8(6) . . ? C2 C3 C4 119.4(6) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 118.6(6) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? C6 C5 C4 120.9(5) . . ? C6 C5 Br1 120.3(5) . . ? C4 C5 Br1 118.8(5) . . ? C5 C6 C7 120.5(6) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C2 C7 C6 118.3(6) . . ? C2 C7 H7A 120.9 . . ? C6 C7 H7A 120.9 . . ? 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 C1 N1 C1 O1 -178.2(3) 4 . . . ? C1 N1 C1 N1 -0.4(11) 4 . . 2 ? C2 O1 C1 N1 0.0(8) . . . . ? C2 O1 C1 N1 -178.1(5) . . . 2 ? C1 O1 C2 C7 119.5(6) . . . . ? C1 O1 C2 C3 -66.4(7) . . . . ? C7 C2 C3 C4 -1.1(8) . . . . ? O1 C2 C3 C4 -174.9(5) . . . . ? C2 C3 C4 C5 0.5(8) . . . . ? C3 C4 C5 C6 0.9(9) . . . . ? C3 C4 C5 Br1 -179.2(4) . . . . ? C4 C5 C6 C7 -1.6(10) . . . . ? Br1 C5 C6 C7 178.5(5) . . . . ? C3 C2 C7 C6 0.4(9) . . . . ? O1 C2 C7 C6 174.4(5) . . . . ? C5 C6 C7 C2 1.0(9) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.299 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.069 data_tris4cl _database_code_depnum_ccdc_archive 'CCDC 198641' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 F15 N3 O3, 0.5(CH3C6H4Cl)' _chemical_formula_sum 'C24.50 H3.50 Cl0.50 F15 N3 O3' _chemical_formula_weight 690.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9681(4) _cell_length_b 13.6038(12) _cell_length_c 16.0136(13) _cell_angle_alpha 111.029(9) _cell_angle_beta 91.527(9) _cell_angle_gamma 96.390(10) _cell_volume 1202.88(17) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 7056 _cell_measurement_theta_min 1.95 _cell_measurement_theta_max 25.93 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.906 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 678 _exptl_absorpt_coefficient_mu 0.258 _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 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9466 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.88 _reflns_number_total 4330 _reflns_number_gt 2794 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _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. ; _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^)+(0.0482P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4330 _refine_ls_number_parameters 426 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 0.870 _refine_ls_restrained_S_all 0.870 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 1.2887(3) 0.79024(11) 0.38107(9) 0.0446(4) Uani 1 1 d . . . F2 F 1.4307(3) 0.75516(12) 0.52931(9) 0.0446(4) Uani 1 1 d . . . F3 F 1.1502(3) 0.63738(13) 0.59818(9) 0.0494(4) Uani 1 1 d . . . F4 F 0.7226(3) 0.56322(12) 0.52540(10) 0.0528(4) Uani 1 1 d . . . F5 F 0.5754(3) 0.60482(12) 0.37974(10) 0.0491(4) Uani 1 1 d . . . F6 F 0.2411(2) 0.71028(11) 0.12040(9) 0.0396(4) Uani 1 1 d . . . F7 F 0.1223(3) 0.90989(12) 0.17842(10) 0.0470(4) Uani 1 1 d . . . F8 F 0.3764(3) 1.06708(11) 0.14447(10) 0.0466(4) Uani 1 1 d . . . F9 F 0.7611(3) 1.02657(10) 0.05603(9) 0.0395(4) Uani 1 1 d . . . F10 F 0.8806(2) 0.82890(10) -0.00012(8) 0.0329(3) Uani 1 1 d . . . F11 F 1.3533(2) 0.48737(11) 0.17331(9) 0.0385(4) Uani 1 1 d . . . F12 F 1.5353(3) 0.39620(12) 0.27998(10) 0.0465(4) Uani 1 1 d . . . F13 F 1.2871(3) 0.23541(12) 0.31278(9) 0.0511(5) Uani 1 1 d . . . F14 F 0.8602(3) 0.16404(11) 0.23751(9) 0.0467(4) Uani 1 1 d . . . F15 F 0.6806(2) 0.25187(10) 0.12689(8) 0.0334(3) Uani 1 1 d . . . O1 O 0.8509(3) 0.72901(12) 0.31170(10) 0.0379(4) Uani 1 1 d . . . O2 O 0.6222(3) 0.66464(11) 0.02468(9) 0.0257(4) Uani 1 1 d . . . O3 O 0.9198(3) 0.40870(11) 0.08831(9) 0.0262(4) Uani 1 1 d . . . N1 N 0.8950(3) 0.56493(13) 0.20577(11) 0.0234(4) Uani 1 1 d . . . N2 N 0.7319(3) 0.69856(13) 0.17127(11) 0.0250(4) Uani 1 1 d . . . N3 N 0.7715(3) 0.53448(13) 0.05437(11) 0.0226(4) Uani 1 1 d . . . C1 C 0.8256(4) 0.65912(16) 0.22607(13) 0.0243(5) Uani 1 1 d . . . C2 C 0.7123(4) 0.63102(16) 0.08700(13) 0.0215(5) Uani 1 1 d . . . C3 C 0.8600(4) 0.50834(15) 0.11865(13) 0.0218(5) Uani 1 1 d . . . C4 C 0.9315(4) 0.69698(18) 0.37865(14) 0.0300(6) Uani 1 1 d . . . C5 C 1.1479(4) 0.73430(18) 0.41646(14) 0.0300(5) Uani 1 1 d . . . C6 C 1.2213(4) 0.71599(18) 0.49102(14) 0.0311(5) Uani 1 1 d . . . C7 C 1.0782(5) 0.65761(19) 0.52651(14) 0.0340(6) Uani 1 1 d . . . C8 C 0.8606(5) 0.61879(18) 0.48912(15) 0.0344(6) Uani 1 1 d . . . C9 C 0.7880(4) 0.63913(18) 0.41539(15) 0.0312(5) Uani 1 1 d . . . C10 C 0.5596(4) 0.76610(16) 0.05746(13) 0.0235(5) Uani 1 1 d . . . C11 C 0.3673(4) 0.78773(17) 0.10299(14) 0.0266(5) Uani 1 1 d . . . C12 C 0.3087(4) 0.88904(19) 0.13369(14) 0.0308(5) Uani 1 1 d . . . C13 C 0.4396(4) 0.96923(17) 0.11749(15) 0.0307(6) Uani 1 1 d . . . C14 C 0.6325(4) 0.94898(16) 0.07238(14) 0.0274(5) Uani 1 1 d . . . C15 C 0.6911(4) 0.84818(17) 0.04314(13) 0.0239(5) Uani 1 1 d . . . C16 C 1.0132(4) 0.37143(16) 0.14975(13) 0.0225(5) Uani 1 1 d . . . C17 C 1.2306(4) 0.40712(17) 0.18830(14) 0.0270(5) Uani 1 1 d . . . C18 C 1.3231(4) 0.36126(18) 0.24254(14) 0.0306(5) Uani 1 1 d . . . C19 C 1.1992(5) 0.27925(18) 0.25836(14) 0.0327(6) Uani 1 1 d . . . C20 C 0.9820(5) 0.24231(17) 0.22020(14) 0.0300(5) Uani 1 1 d . . . C21 C 0.8902(4) 0.28834(16) 0.16545(13) 0.0242(5) Uani 1 1 d . . . Cl1 Cl 0.3061(8) 0.0183(6) 0.6655(5) 0.0488(9) Uani 0.498(8) 1 d P A 1 C30 C 0.297(4) 0.007(2) 0.6549(15) 0.076(13) Uani 0.502(8) 1 d P A 2 H30A H 0.4478 0.0438 0.6540 0.115 Uiso 0.502(8) 1 calc PR A 2 H30B H 0.3089 -0.0662 0.6487 0.115 Uiso 0.502(8) 1 calc PR A 2 H30C H 0.2331 0.0440 0.7118 0.115 Uiso 0.502(8) 1 calc PR A 2 C31 C 0.1382(5) 0.00815(18) 0.57437(16) 0.0353(6) Uani 1 1 d . . . C32 C -0.0817(5) -0.0407(2) 0.56272(17) 0.0403(6) Uani 1 1 d . . . H32 H -0.1392 -0.0687 0.6055 0.048 Uiso 1 1 calc R . . C33 C 0.2194(5) 0.0491(2) 0.51180(17) 0.0401(6) Uani 1 1 d . . . H33 H 0.3705 0.0832 0.5197 0.048 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 0.0489(11) 0.0441(8) 0.0402(8) 0.0169(7) 0.0042(7) -0.0016(7) F2 0.0300(10) 0.0585(10) 0.0360(7) 0.0061(7) -0.0090(6) 0.0084(7) F3 0.0666(12) 0.0621(10) 0.0266(7) 0.0194(7) 0.0032(7) 0.0264(8) F4 0.0587(12) 0.0478(9) 0.0512(9) 0.0177(8) 0.0220(8) 0.0005(8) F5 0.0266(10) 0.0490(9) 0.0516(9) -0.0052(7) -0.0062(7) 0.0044(7) F6 0.0314(9) 0.0404(8) 0.0448(8) 0.0154(7) 0.0058(6) -0.0050(6) F7 0.0272(10) 0.0587(10) 0.0494(8) 0.0091(7) 0.0105(7) 0.0158(7) F8 0.0543(11) 0.0318(8) 0.0514(9) 0.0070(6) 0.0040(7) 0.0240(7) F9 0.0538(11) 0.0249(7) 0.0403(8) 0.0133(6) 0.0063(7) 0.0022(6) F10 0.0312(9) 0.0323(7) 0.0352(7) 0.0106(6) 0.0126(6) 0.0070(6) F11 0.0333(9) 0.0372(8) 0.0412(8) 0.0122(6) 0.0064(6) -0.0051(6) F12 0.0299(10) 0.0504(9) 0.0454(8) -0.0002(7) -0.0108(7) 0.0122(7) F13 0.0752(13) 0.0477(9) 0.0343(8) 0.0156(7) -0.0120(7) 0.0253(8) F14 0.0707(12) 0.0345(8) 0.0384(8) 0.0211(6) 0.0010(7) -0.0045(7) F15 0.0291(9) 0.0325(7) 0.0350(7) 0.0099(6) -0.0034(6) -0.0025(6) O1 0.0575(13) 0.0298(9) 0.0215(8) 0.0001(6) -0.0104(7) 0.0201(8) O2 0.0322(11) 0.0218(7) 0.0224(7) 0.0066(6) -0.0029(6) 0.0067(6) O3 0.0376(11) 0.0187(7) 0.0215(7) 0.0055(6) -0.0006(6) 0.0078(7) N1 0.0253(12) 0.0196(9) 0.0228(9) 0.0047(7) 0.0001(7) 0.0036(7) N2 0.0264(12) 0.0243(9) 0.0224(9) 0.0060(7) -0.0026(7) 0.0052(8) N3 0.0248(12) 0.0198(9) 0.0229(9) 0.0077(7) 0.0009(7) 0.0025(7) C1 0.0226(14) 0.0253(11) 0.0213(10) 0.0043(9) -0.0015(9) 0.0038(9) C2 0.0193(13) 0.0206(10) 0.0243(10) 0.0089(8) -0.0006(8) -0.0001(8) C3 0.0199(14) 0.0179(10) 0.0269(11) 0.0076(8) 0.0027(9) 0.0014(8) C4 0.0372(17) 0.0287(12) 0.0209(10) 0.0022(9) -0.0039(10) 0.0154(10) C5 0.0331(16) 0.0298(12) 0.0237(11) 0.0050(9) 0.0033(10) 0.0062(10) C6 0.0237(15) 0.0363(13) 0.0265(11) 0.0024(10) -0.0040(10) 0.0089(10) C7 0.0427(18) 0.0393(13) 0.0209(11) 0.0082(10) 0.0026(10) 0.0189(12) C8 0.0392(17) 0.0307(12) 0.0308(12) 0.0063(10) 0.0112(11) 0.0091(11) C9 0.0232(15) 0.0295(12) 0.0307(12) -0.0021(9) -0.0010(10) 0.0076(10) C10 0.0248(14) 0.0232(11) 0.0210(10) 0.0058(8) -0.0031(9) 0.0054(9) C11 0.0218(15) 0.0282(12) 0.0290(11) 0.0107(9) -0.0010(9) -0.0003(9) C12 0.0202(15) 0.0402(13) 0.0275(11) 0.0055(10) 0.0005(9) 0.0094(10) C13 0.0345(17) 0.0254(12) 0.0294(11) 0.0045(9) -0.0027(10) 0.0125(10) C14 0.0341(16) 0.0217(11) 0.0260(11) 0.0090(9) -0.0019(10) 0.0025(10) C15 0.0215(14) 0.0273(11) 0.0215(10) 0.0069(9) -0.0007(9) 0.0056(9) C16 0.0264(14) 0.0212(10) 0.0191(9) 0.0052(8) 0.0016(9) 0.0078(9) C17 0.0265(15) 0.0253(11) 0.0255(11) 0.0043(9) 0.0053(9) 0.0041(9) C18 0.0251(15) 0.0323(12) 0.0283(11) 0.0017(9) -0.0024(10) 0.0113(10) C19 0.0467(18) 0.0310(12) 0.0216(11) 0.0070(9) -0.0001(10) 0.0186(11) C20 0.0423(17) 0.0224(11) 0.0255(11) 0.0084(9) 0.0054(10) 0.0055(10) C21 0.0235(14) 0.0245(11) 0.0216(10) 0.0045(9) 0.0009(9) 0.0046(9) Cl1 0.047(2) 0.0540(18) 0.0430(13) 0.0147(15) -0.0060(12) 0.0096(13) C30 0.083(19) 0.057(11) 0.063(15) -0.006(6) -0.002(8) -0.001(7) C31 0.0396(18) 0.0287(12) 0.0344(13) 0.0060(10) 0.0030(11) 0.0094(11) C32 0.0430(19) 0.0364(14) 0.0419(14) 0.0141(11) 0.0095(12) 0.0057(12) C33 0.0340(18) 0.0343(14) 0.0478(15) 0.0107(11) 0.0050(12) 0.0014(11) _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 C5 1.341(3) . ? F2 C6 1.341(3) . ? F3 C7 1.343(3) . ? F4 C8 1.338(3) . ? F5 C9 1.339(3) . ? F6 C11 1.342(3) . ? F7 C12 1.341(3) . ? F8 C13 1.345(3) . ? F9 C14 1.342(3) . ? F10 C15 1.344(3) . ? F11 C17 1.343(3) . ? F12 C18 1.345(3) . ? F13 C19 1.345(3) . ? F14 C20 1.338(3) . ? F15 C21 1.339(3) . ? O1 C1 1.352(2) . ? O1 C4 1.387(3) . ? O2 C2 1.359(2) . ? O2 C10 1.388(3) . ? O3 C3 1.358(2) . ? O3 C16 1.388(3) . ? N1 C1 1.321(3) . ? N1 C3 1.327(3) . ? N2 C1 1.323(3) . ? N2 C2 1.325(3) . ? N3 C3 1.319(3) . ? N3 C2 1.320(3) . ? C4 C5 1.373(3) . ? C4 C9 1.381(4) . ? C5 C6 1.374(3) . ? C6 C7 1.372(4) . ? C7 C8 1.380(4) . ? C8 C9 1.376(3) . ? C10 C11 1.379(3) . ? C10 C15 1.383(3) . ? C11 C12 1.376(3) . ? C12 C13 1.376(4) . ? C13 C14 1.376(3) . ? C14 C15 1.370(3) . ? C16 C17 1.379(3) . ? C16 C21 1.382(3) . ? C17 C18 1.374(3) . ? C18 C19 1.373(4) . ? C19 C20 1.378(4) . ? C20 C21 1.381(3) . ? Cl1 C31 1.703(6) . ? C30 C31 1.58(2) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.379(4) . ? C31 C33 1.384(4) . ? C32 C33 1.394(4) 2_556 ? C32 H32 0.9500 . ? C33 C32 1.394(4) 2_556 ? C33 H33 0.9500 . ? 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 C1 O1 C4 119.07(17) . . ? C2 O2 C10 115.62(15) . . ? C3 O3 C16 118.52(15) . . ? C1 N1 C3 111.47(18) . . ? C1 N2 C2 111.91(18) . . ? C3 N3 C2 110.96(17) . . ? N1 C1 N2 127.94(19) . . ? N1 C1 O1 120.11(19) . . ? N2 C1 O1 111.94(18) . . ? N3 C2 N2 128.61(19) . . ? N3 C2 O2 114.64(17) . . ? N2 C2 O2 116.74(18) . . ? N3 C3 N1 129.09(19) . . ? N3 C3 O3 112.99(17) . . ? N1 C3 O3 117.92(18) . . ? C5 C4 C9 119.4(2) . . ? C5 C4 O1 119.6(2) . . ? C9 C4 O1 120.5(2) . . ? F1 C5 C4 119.8(2) . . ? F1 C5 C6 119.5(2) . . ? C4 C5 C6 120.7(2) . . ? F2 C6 C7 120.0(2) . . ? F2 C6 C5 120.5(2) . . ? C7 C6 C5 119.5(2) . . ? F3 C7 C6 119.9(2) . . ? F3 C7 C8 119.4(2) . . ? C6 C7 C8 120.7(2) . . ? F4 C8 C9 121.0(2) . . ? F4 C8 C7 119.8(2) . . ? C9 C8 C7 119.2(2) . . ? F5 C9 C8 120.1(2) . . ? F5 C9 C4 119.4(2) . . ? C8 C9 C4 120.5(2) . . ? C11 C10 C15 118.57(19) . . ? C11 C10 O2 121.97(19) . . ? C15 C10 O2 119.5(2) . . ? F6 C11 C12 119.7(2) . . ? F6 C11 C10 119.73(19) . . ? C12 C11 C10 120.5(2) . . ? F7 C12 C13 119.6(2) . . ? F7 C12 C11 120.3(2) . . ? C13 C12 C11 120.1(2) . . ? F8 C13 C12 119.8(2) . . ? F8 C13 C14 120.1(2) . . ? C12 C13 C14 120.1(2) . . ? F9 C14 C15 120.0(2) . . ? F9 C14 C13 120.62(19) . . ? C15 C14 C13 119.3(2) . . ? F10 C15 C14 119.2(2) . . ? F10 C15 C10 119.42(19) . . ? C14 C15 C10 121.4(2) . . ? C17 C16 C21 119.32(19) . . ? C17 C16 O3 122.36(19) . . ? C21 C16 O3 118.0(2) . . ? F11 C17 C18 119.5(2) . . ? F11 C17 C16 120.2(2) . . ? C18 C17 C16 120.3(2) . . ? F12 C18 C19 119.8(2) . . ? F12 C18 C17 120.2(2) . . ? C19 C18 C17 120.0(2) . . ? F13 C19 C18 120.3(2) . . ? F13 C19 C20 119.2(2) . . ? C18 C19 C20 120.5(2) . . ? F14 C20 C19 120.2(2) . . ? F14 C20 C21 120.5(2) . . ? C19 C20 C21 119.3(2) . . ? F15 C21 C20 119.8(2) . . ? F15 C21 C16 119.69(19) . . ? C20 C21 C16 120.6(2) . . ? C31 C30 H30A 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C31 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C32 C31 C33 119.4(2) . . ? C32 C31 C30 118.8(9) . . ? C33 C31 C30 121.6(10) . . ? C32 C31 Cl1 119.9(3) . . ? C33 C31 Cl1 120.7(3) . . ? C30 C31 Cl1 4.8(12) . . ? C31 C32 C33 120.0(2) . 2_556 ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 2_556 . ? C31 C33 C32 120.6(3) . 2_556 ? C31 C33 H33 119.7 . . ? C32 C33 H33 119.7 2_556 . ? 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 C3 N1 C1 N2 -0.1(3) . . . . ? C3 N1 C1 O1 -178.9(2) . . . . ? C2 N2 C1 N1 -0.4(3) . . . . ? C2 N2 C1 O1 178.45(19) . . . . ? C4 O1 C1 N1 -5.7(3) . . . . ? C4 O1 C1 N2 175.3(2) . . . . ? C3 N3 C2 N2 0.0(3) . . . . ? C3 N3 C2 O2 179.11(19) . . . . ? C1 N2 C2 N3 0.4(3) . . . . ? C1 N2 C2 O2 -178.6(2) . . . . ? C10 O2 C2 N3 -179.75(19) . . . . ? C10 O2 C2 N2 -0.6(3) . . . . ? C2 N3 C3 N1 -0.7(3) . . . . ? C2 N3 C3 O3 178.89(18) . . . . ? C1 N1 C3 N3 0.7(3) . . . . ? C1 N1 C3 O3 -178.9(2) . . . . ? C16 O3 C3 N3 -179.40(19) . . . . ? C16 O3 C3 N1 0.2(3) . . . . ? C1 O1 C4 C5 107.0(2) . . . . ? C1 O1 C4 C9 -81.3(3) . . . . ? C9 C4 C5 F1 179.8(2) . . . . ? O1 C4 C5 F1 -8.4(3) . . . . ? C9 C4 C5 C6 -1.0(3) . . . . ? O1 C4 C5 C6 170.8(2) . . . . ? F1 C5 C6 F2 1.2(3) . . . . ? C4 C5 C6 F2 -178.08(19) . . . . ? F1 C5 C6 C7 -179.2(2) . . . . ? C4 C5 C6 C7 1.6(3) . . . . ? F2 C6 C7 F3 -1.8(3) . . . . ? C5 C6 C7 F3 178.5(2) . . . . ? F2 C6 C7 C8 178.5(2) . . . . ? C5 C6 C7 C8 -1.1(3) . . . . ? F3 C7 C8 F4 1.2(3) . . . . ? C6 C7 C8 F4 -179.1(2) . . . . ? F3 C7 C8 C9 -179.6(2) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? F4 C8 C9 F5 1.2(3) . . . . ? C7 C8 C9 F5 -178.03(19) . . . . ? F4 C8 C9 C4 179.72(19) . . . . ? C7 C8 C9 C4 0.5(3) . . . . ? C5 C4 C9 F5 178.48(19) . . . . ? O1 C4 C9 F5 6.7(3) . . . . ? C5 C4 C9 C8 -0.1(3) . . . . ? O1 C4 C9 C8 -171.81(19) . . . . ? C2 O2 C10 C11 -75.3(3) . . . . ? C2 O2 C10 C15 105.7(2) . . . . ? C15 C10 C11 F6 -177.76(19) . . . . ? O2 C10 C11 F6 3.3(3) . . . . ? C15 C10 C11 C12 -0.2(3) . . . . ? O2 C10 C11 C12 -179.2(2) . . . . ? F6 C11 C12 F7 -2.1(3) . . . . ? C10 C11 C12 F7 -179.59(19) . . . . ? F6 C11 C12 C13 178.8(2) . . . . ? C10 C11 C12 C13 1.3(3) . . . . ? F7 C12 C13 F8 -1.8(3) . . . . ? C11 C12 C13 F8 177.3(2) . . . . ? F7 C12 C13 C14 179.4(2) . . . . ? C11 C12 C13 C14 -1.5(3) . . . . ? F8 C13 C14 F9 1.0(3) . . . . ? C12 C13 C14 F9 179.8(2) . . . . ? F8 C13 C14 C15 -178.2(2) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? F9 C14 C15 F10 1.4(3) . . . . ? C13 C14 C15 F10 -179.37(19) . . . . ? F9 C14 C15 C10 -178.75(19) . . . . ? C13 C14 C15 C10 0.5(3) . . . . ? C11 C10 C15 F10 179.18(18) . . . . ? O2 C10 C15 F10 -1.8(3) . . . . ? C11 C10 C15 C14 -0.6(3) . . . . ? O2 C10 C15 C14 178.36(19) . . . . ? C3 O3 C16 C17 -73.2(3) . . . . ? C3 O3 C16 C21 113.3(2) . . . . ? C21 C16 C17 F11 179.56(18) . . . . ? O3 C16 C17 F11 6.1(3) . . . . ? C21 C16 C17 C18 -0.7(3) . . . . ? O3 C16 C17 C18 -174.13(19) . . . . ? F11 C17 C18 F12 -0.3(3) . . . . ? C16 C17 C18 F12 179.94(19) . . . . ? F11 C17 C18 C19 179.95(19) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? F12 C18 C19 F13 1.6(3) . . . . ? C17 C18 C19 F13 -178.7(2) . . . . ? F12 C18 C19 C20 -179.7(2) . . . . ? C17 C18 C19 C20 0.0(3) . . . . ? F13 C19 C20 F14 0.3(3) . . . . ? C18 C19 C20 F14 -178.4(2) . . . . ? F13 C19 C20 C21 178.98(19) . . . . ? C18 C19 C20 C21 0.3(3) . . . . ? F14 C20 C21 F15 -2.4(3) . . . . ? C19 C20 C21 F15 178.93(19) . . . . ? F14 C20 C21 C16 177.95(19) . . . . ? C19 C20 C21 C16 -0.8(3) . . . . ? C17 C16 C21 F15 -178.72(18) . . . . ? O3 C16 C21 F15 -5.0(3) . . . . ? C17 C16 C21 C20 1.0(3) . . . . ? O3 C16 C21 C20 174.70(19) . . . . ? C33 C31 C32 C33 0.4(4) . . . 2_556 ? C30 C31 C32 C33 -174.6(11) . . . 2_556 ? Cl1 C31 C32 C33 180.0(3) . . . 2_556 ? C32 C31 C33 C32 -0.4(4) . . . 2_556 ? C30 C31 C33 C32 174.5(12) . . . 2_556 ? Cl1 C31 C33 C32 -180.0(3) . . . 2_556 ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 25.88 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.224 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.051 data_tris5f3n _database_code_depnum_ccdc_archive 'CCDC 198642' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H5 F15 N3 O3' _chemical_formula_weight 680.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' O O 0.0106 0.0060 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9555(5) _cell_length_b 13.5912(12) _cell_length_c 16.1207(14) _cell_angle_alpha 111.055(10) _cell_angle_beta 91.871(10) _cell_angle_gamma 95.776(10) _cell_volume 1208.22(18) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6606 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.90 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 670 _exptl_absorpt_coefficient_mu 0.202 _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 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9569 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0752 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.90 _reflns_number_total 4379 _reflns_number_gt 2736 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _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. ; _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^)+(0.0537P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0110(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4379 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 0.845 _refine_ls_restrained_S_all 0.845 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F -0.2853(3) 0.21039(12) 0.11973(10) 0.0458(4) Uani 1 1 d . . . F2 F -0.4249(3) 0.24545(13) -0.02843(10) 0.0480(4) Uani 1 1 d . . . F3 F -0.1432(3) 0.36170(14) -0.09623(9) 0.0532(5) Uani 1 1 d . . . F4 F 0.2836(3) 0.43561(13) -0.02168(11) 0.0558(5) Uani 1 1 d . . . F5 F 0.4285(3) 0.39392(13) 0.12389(11) 0.0509(5) Uani 1 1 d . . . F6 F -0.3563(3) 0.51464(11) 0.32653(9) 0.0394(4) Uani 1 1 d . . . F7 F -0.5362(3) 0.60550(13) 0.21827(10) 0.0465(4) Uani 1 1 d . . . F8 F -0.2870(3) 0.76407(12) 0.18574(9) 0.0514(5) Uani 1 1 d . . . F9 F 0.1397(3) 0.83456(12) 0.26223(10) 0.0462(4) Uani 1 1 d . . . F10 F 0.3176(2) 0.74662(11) 0.37322(9) 0.0345(3) Uani 1 1 d . . . F11 F 0.1185(2) 0.17181(10) 0.49992(9) 0.0339(3) Uani 1 1 d . . . F12 F 0.2353(3) -0.02722(11) 0.44351(9) 0.0411(4) Uani 1 1 d . . . F13 F 0.6206(3) -0.07006(11) 0.35625(10) 0.0483(4) Uani 1 1 d . . . F14 F 0.8780(3) 0.08643(13) 0.32375(10) 0.0488(4) Uani 1 1 d . . . F15 F 0.7610(3) 0.28692(12) 0.38201(10) 0.0414(4) Uani 1 1 d . . . O1 O 0.1515(3) 0.27113(13) 0.19044(10) 0.0389(5) Uani 1 1 d . . . O2 O 0.0769(3) 0.59163(11) 0.41202(10) 0.0275(4) Uani 1 1 d . . . O3 O 0.3794(3) 0.33530(11) 0.47641(10) 0.0263(4) Uani 1 1 d . . . N1 N 0.2689(3) 0.30091(14) 0.33042(12) 0.0258(4) Uani 1 1 d . . . N2 N 0.1052(3) 0.43478(14) 0.29530(11) 0.0239(4) Uani 1 1 d . . . N3 N 0.2281(3) 0.46515(14) 0.44589(12) 0.0238(4) Uani 1 1 d . . . C1 C 0.1748(4) 0.34005(18) 0.27540(14) 0.0259(5) Uani 1 1 d . . . C2 C 0.1384(4) 0.49186(17) 0.38188(14) 0.0225(5) Uani 1 1 d . . . C3 C 0.2877(4) 0.36847(17) 0.41379(14) 0.0220(5) Uani 1 1 d . . . C4 C 0.0719(4) 0.30304(18) 0.12336(14) 0.0297(6) Uani 1 1 d . . . C5 C -0.1450(4) 0.26605(19) 0.08526(15) 0.0295(6) Uani 1 1 d . . . C6 C -0.2154(4) 0.2847(2) 0.01064(15) 0.0328(6) Uani 1 1 d . . . C7 C -0.0721(5) 0.3428(2) -0.02392(15) 0.0340(6) Uani 1 1 d . . . C8 C 0.1441(5) 0.3805(2) 0.01420(16) 0.0350(6) Uani 1 1 d . . . C9 C 0.2162(4) 0.3599(2) 0.08772(16) 0.0331(6) Uani 1 1 d . . . C10 C -0.0158(4) 0.62866(17) 0.35010(14) 0.0239(5) Uani 1 1 d . . . C11 C -0.2340(4) 0.59317(18) 0.31091(15) 0.0276(5) Uani 1 1 d . . . C12 C -0.3241(4) 0.63917(19) 0.25583(15) 0.0326(6) Uani 1 1 d . . . C13 C -0.1994(5) 0.7204(2) 0.24031(15) 0.0344(6) Uani 1 1 d . . . C14 C 0.0171(4) 0.75630(18) 0.27896(15) 0.0298(6) Uani 1 1 d . . . C15 C 0.1072(4) 0.71021(18) 0.33384(14) 0.0256(5) Uani 1 1 d . . . C16 C 0.4410(4) 0.23292(17) 0.44383(14) 0.0239(5) Uani 1 1 d . . . C17 C 0.3086(4) 0.15189(18) 0.45746(14) 0.0248(5) Uani 1 1 d . . . C18 C 0.3658(4) 0.05000(18) 0.42786(15) 0.0283(6) Uani 1 1 d . . . C19 C 0.5583(4) 0.02841(19) 0.38358(15) 0.0330(6) Uani 1 1 d . . . C20 C 0.6912(4) 0.1081(2) 0.36800(15) 0.0323(6) Uani 1 1 d . . . C21 C 0.6341(4) 0.21023(18) 0.39850(15) 0.0272(5) Uani 1 1 d . . . C30 C 0.2930(6) 0.0197(2) 0.15705(19) 0.0518(8) Uani 1 1 d . . . H34A H 0.2479 0.0756 0.2095 0.078 Uiso 1 1 calc R . . H34B H 0.4506 0.0383 0.1472 0.078 Uiso 1 1 calc R . . H34C H 0.2786 -0.0478 0.1668 0.078 Uiso 1 1 calc R . . C31 C 0.1410(5) 0.0086(2) 0.07589(18) 0.0414(7) Uani 1 1 d . . . C32 C 0.2153(5) 0.0488(2) 0.01390(19) 0.0439(7) Uani 1 1 d . . . H31 H 0.3655 0.0835 0.0219 0.053 Uiso 1 1 calc R . . C33 C -0.0771(5) -0.0407(2) 0.0615(2) 0.0482(7) Uani 1 1 d . . . H32 H -0.1357 -0.0699 0.1029 0.058 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 0.0489(10) 0.0444(9) 0.0454(9) 0.0193(7) 0.0080(7) -0.0008(8) F2 0.0310(9) 0.0637(10) 0.0405(8) 0.0089(8) -0.0086(7) 0.0080(8) F3 0.0746(13) 0.0659(11) 0.0281(8) 0.0219(7) 0.0056(7) 0.0312(10) F4 0.0621(12) 0.0482(10) 0.0579(10) 0.0197(8) 0.0249(9) 0.0024(9) F5 0.0292(9) 0.0509(9) 0.0544(10) -0.0015(8) -0.0059(7) 0.0031(8) F6 0.0341(9) 0.0386(8) 0.0434(8) 0.0153(7) 0.0053(7) -0.0071(7) F7 0.0297(9) 0.0530(9) 0.0469(9) 0.0058(7) -0.0084(7) 0.0100(7) F8 0.0744(13) 0.0486(9) 0.0366(8) 0.0190(7) -0.0099(8) 0.0229(9) F9 0.0678(12) 0.0354(8) 0.0400(8) 0.0225(7) 0.0010(8) -0.0050(8) F10 0.0310(8) 0.0342(7) 0.0358(8) 0.0120(6) -0.0024(6) -0.0025(6) F11 0.0324(9) 0.0331(8) 0.0380(8) 0.0131(6) 0.0135(6) 0.0073(6) F12 0.0534(11) 0.0273(8) 0.0454(8) 0.0172(7) 0.0075(7) 0.0014(7) F13 0.0559(11) 0.0321(8) 0.0545(9) 0.0084(7) 0.0044(8) 0.0226(8) F14 0.0292(9) 0.0610(10) 0.0513(9) 0.0110(8) 0.0127(7) 0.0166(8) F15 0.0318(9) 0.0427(9) 0.0481(9) 0.0169(7) 0.0077(7) -0.0055(7) O1 0.0592(13) 0.0303(9) 0.0241(9) 0.0033(7) -0.0081(8) 0.0197(9) O2 0.0394(10) 0.0205(8) 0.0231(8) 0.0076(6) 0.0003(7) 0.0078(7) O3 0.0332(10) 0.0214(8) 0.0250(8) 0.0092(6) -0.0008(7) 0.0048(7) N1 0.0268(11) 0.0256(10) 0.0246(10) 0.0088(8) -0.0022(8) 0.0045(9) N2 0.0246(11) 0.0217(9) 0.0253(10) 0.0079(8) 0.0025(8) 0.0043(8) N3 0.0247(11) 0.0209(9) 0.0260(9) 0.0091(8) 0.0013(8) 0.0013(8) C1 0.0242(13) 0.0265(12) 0.0241(11) 0.0058(10) 0.0010(9) 0.0032(10) C2 0.0199(12) 0.0197(11) 0.0269(11) 0.0077(9) 0.0028(9) 0.0004(9) C3 0.0190(12) 0.0221(11) 0.0257(11) 0.0105(9) -0.0001(9) 0.0000(9) C4 0.0379(15) 0.0281(12) 0.0199(11) 0.0027(9) -0.0046(10) 0.0140(11) C5 0.0292(14) 0.0288(12) 0.0275(12) 0.0061(10) 0.0054(10) 0.0041(11) C6 0.0255(14) 0.0387(14) 0.0277(12) 0.0034(11) -0.0029(10) 0.0094(12) C7 0.0409(17) 0.0401(14) 0.0237(12) 0.0119(11) 0.0030(11) 0.0166(13) C8 0.0390(17) 0.0314(13) 0.0357(14) 0.0116(11) 0.0157(12) 0.0071(12) C9 0.0271(15) 0.0320(13) 0.0309(13) -0.0008(11) -0.0002(11) 0.0092(11) C10 0.0284(13) 0.0212(11) 0.0227(11) 0.0072(9) 0.0055(9) 0.0079(10) C11 0.0263(14) 0.0258(12) 0.0286(12) 0.0070(10) 0.0066(10) 0.0031(11) C12 0.0272(14) 0.0334(13) 0.0300(12) 0.0017(11) -0.0025(10) 0.0087(11) C13 0.0480(17) 0.0334(13) 0.0225(12) 0.0083(10) -0.0019(11) 0.0170(13) C14 0.0429(16) 0.0229(11) 0.0259(12) 0.0107(10) 0.0063(11) 0.0055(11) C15 0.0259(14) 0.0243(11) 0.0242(11) 0.0057(9) 0.0018(9) 0.0035(10) C16 0.0252(13) 0.0237(11) 0.0214(11) 0.0063(9) -0.0021(9) 0.0045(10) C17 0.0233(13) 0.0285(12) 0.0231(11) 0.0092(9) 0.0018(9) 0.0064(10) C18 0.0319(15) 0.0259(12) 0.0294(12) 0.0135(10) 0.0001(10) 0.0014(11) C19 0.0381(16) 0.0267(13) 0.0313(13) 0.0047(10) -0.0022(11) 0.0141(12) C20 0.0225(14) 0.0416(14) 0.0302(12) 0.0080(11) 0.0033(10) 0.0101(12) C21 0.0203(13) 0.0297(12) 0.0313(12) 0.0120(10) -0.0002(10) -0.0013(11) C30 0.058(2) 0.0461(17) 0.0508(17) 0.0155(14) 0.0031(15) 0.0138(15) C31 0.0429(18) 0.0286(13) 0.0487(16) 0.0080(12) 0.0087(13) 0.0076(13) C32 0.0344(17) 0.0364(15) 0.0526(17) 0.0064(13) 0.0016(13) 0.0042(13) C33 0.049(2) 0.0383(15) 0.0541(18) 0.0119(13) 0.0117(14) 0.0079(14) _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 C5 1.336(3) . ? F2 C6 1.346(3) . ? F3 C7 1.345(3) . ? F4 C8 1.343(3) . ? F5 C9 1.339(3) . ? F6 C11 1.335(3) . ? F7 C12 1.344(3) . ? F8 C13 1.344(3) . ? F9 C14 1.342(3) . ? F10 C15 1.347(3) . ? F11 C17 1.343(3) . ? F12 C18 1.344(3) . ? F13 C19 1.345(3) . ? F14 C20 1.342(3) . ? F15 C21 1.335(3) . ? O1 C1 1.346(3) . ? O1 C4 1.388(3) . ? O2 C2 1.359(2) . ? O2 C10 1.391(2) . ? O3 C3 1.364(2) . ? O3 C16 1.392(3) . ? N1 C1 1.323(3) . ? N1 C3 1.321(3) . ? N2 C1 1.324(3) . ? N2 C2 1.327(3) . ? N3 C3 1.318(3) . ? N3 C2 1.324(3) . ? C4 C9 1.372(4) . ? C4 C5 1.376(3) . ? C5 C6 1.376(3) . ? C6 C7 1.369(4) . ? C7 C8 1.374(4) . ? C8 C9 1.377(3) . ? C10 C15 1.375(3) . ? C10 C11 1.386(3) . ? C11 C12 1.379(3) . ? C12 C13 1.370(4) . ? C13 C14 1.375(4) . ? C14 C15 1.378(3) . ? C16 C17 1.376(3) . ? C16 C21 1.384(3) . ? C17 C18 1.375(3) . ? C18 C19 1.372(4) . ? C19 C20 1.378(4) . ? C20 C21 1.378(3) . ? C30 C31 1.519(4) . ? C30 H34A 0.9800 . ? C30 H34B 0.9800 . ? C30 H34C 0.9800 . ? C31 C32 1.365(4) . ? C31 C33 1.373(4) . ? C32 C33 1.409(4) 2 ? C32 H31 0.9500 . ? C33 C32 1.409(4) 2 ? C33 H32 0.9500 . ? 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 C1 O1 C4 119.69(17) . . ? C2 O2 C10 118.04(16) . . ? C3 O3 C16 115.17(16) . . ? C1 N1 C3 112.09(18) . . ? C1 N2 C2 111.82(18) . . ? C3 N3 C2 111.26(18) . . ? N1 C1 N2 127.7(2) . . ? N1 C1 O1 112.55(19) . . ? N2 C1 O1 119.77(19) . . ? N3 C2 N2 128.45(19) . . ? N3 C2 O2 113.18(18) . . ? N2 C2 O2 118.37(18) . . ? N3 C3 N1 128.70(19) . . ? N3 C3 O3 114.38(18) . . ? N1 C3 O3 116.91(18) . . ? C9 C4 C5 119.9(2) . . ? C9 C4 O1 120.3(2) . . ? C5 C4 O1 119.3(2) . . ? F1 C5 C4 120.0(2) . . ? F1 C5 C6 120.1(2) . . ? C4 C5 C6 119.9(2) . . ? F2 C6 C7 120.1(2) . . ? F2 C6 C5 119.9(2) . . ? C7 C6 C5 120.0(2) . . ? F3 C7 C6 119.6(2) . . ? F3 C7 C8 120.1(3) . . ? C6 C7 C8 120.3(2) . . ? F4 C8 C7 119.4(2) . . ? F4 C8 C9 120.9(2) . . ? C7 C8 C9 119.7(2) . . ? F5 C9 C4 119.7(2) . . ? F5 C9 C8 120.1(3) . . ? C4 C9 C8 120.2(2) . . ? C15 C10 C11 119.2(2) . . ? C15 C10 O2 118.2(2) . . ? C11 C10 O2 122.3(2) . . ? F6 C11 C12 120.2(2) . . ? F6 C11 C10 120.0(2) . . ? C12 C11 C10 119.9(2) . . ? F7 C12 C13 119.7(2) . . ? F7 C12 C11 120.0(2) . . ? C13 C12 C11 120.2(2) . . ? F8 C13 C12 120.0(2) . . ? F8 C13 C14 119.6(2) . . ? C12 C13 C14 120.4(2) . . ? F9 C14 C15 120.5(2) . . ? F9 C14 C13 120.1(2) . . ? C15 C14 C13 119.4(2) . . ? F10 C15 C10 119.51(19) . . ? F10 C15 C14 119.5(2) . . ? C10 C15 C14 121.0(2) . . ? C17 C16 C21 118.8(2) . . ? C17 C16 O3 119.5(2) . . ? C21 C16 O3 121.7(2) . . ? F11 C17 C16 119.72(19) . . ? F11 C17 C18 118.9(2) . . ? C16 C17 C18 121.4(2) . . ? F12 C18 C19 120.5(2) . . ? F12 C18 C17 120.1(2) . . ? C19 C18 C17 119.4(2) . . ? F13 C19 C18 120.4(2) . . ? F13 C19 C20 119.6(2) . . ? C18 C19 C20 120.0(2) . . ? F14 C20 C19 119.9(2) . . ? F14 C20 C21 119.9(2) . . ? C19 C20 C21 120.2(2) . . ? F15 C21 C20 120.1(2) . . ? F15 C21 C16 119.7(2) . . ? C20 C21 C16 120.1(2) . . ? C31 C30 H34A 109.5 . . ? C31 C30 H34B 109.5 . . ? H34A C30 H34B 109.5 . . ? C31 C30 H34C 109.5 . . ? H34A C30 H34C 109.5 . . ? H34B C30 H34C 109.5 . . ? C32 C31 C33 116.7(3) . . ? C32 C31 C30 121.2(3) . . ? C33 C31 C30 122.1(3) . . ? C31 C32 C33 122.4(3) . 2 ? C31 C32 H31 118.8 . . ? C33 C32 H31 118.8 2 . ? C31 C33 C32 121.0(3) . 2 ? C31 C33 H32 119.5 . . ? C32 C33 H32 119.5 2 . ? 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 C3 N1 C1 N2 0.7(4) . . . . ? C3 N1 C1 O1 -179.0(2) . . . . ? C2 N2 C1 N1 -0.5(4) . . . . ? C2 N2 C1 O1 179.3(2) . . . . ? C4 O1 C1 N1 -175.0(2) . . . . ? C4 O1 C1 N2 5.3(3) . . . . ? C3 N3 C2 N2 0.1(3) . . . . ? C3 N3 C2 O2 -179.3(2) . . . . ? C1 N2 C2 N3 0.0(3) . . . . ? C1 N2 C2 O2 179.4(2) . . . . ? C10 O2 C2 N3 178.9(2) . . . . ? C10 O2 C2 N2 -0.6(3) . . . . ? C2 N3 C3 N1 0.2(3) . . . . ? C2 N3 C3 O3 -179.3(2) . . . . ? C1 N1 C3 N3 -0.6(3) . . . . ? C1 N1 C3 O3 178.9(2) . . . . ? C16 O3 C3 N3 179.3(2) . . . . ? C16 O3 C3 N1 -0.3(3) . . . . ? C1 O1 C4 C9 81.6(3) . . . . ? C1 O1 C4 C5 -106.5(3) . . . . ? C9 C4 C5 F1 179.8(2) . . . . ? O1 C4 C5 F1 7.8(3) . . . . ? C9 C4 C5 C6 1.1(3) . . . . ? O1 C4 C5 C6 -170.9(2) . . . . ? F1 C5 C6 F2 -1.0(3) . . . . ? C4 C5 C6 F2 177.8(2) . . . . ? F1 C5 C6 C7 179.2(2) . . . . ? C4 C5 C6 C7 -2.1(3) . . . . ? F2 C6 C7 F3 1.0(3) . . . . ? C5 C6 C7 F3 -179.2(2) . . . . ? F2 C6 C7 C8 -178.2(2) . . . . ? C5 C6 C7 C8 1.6(3) . . . . ? F3 C7 C8 F4 -0.4(3) . . . . ? C6 C7 C8 F4 178.7(2) . . . . ? F3 C7 C8 C9 -179.4(2) . . . . ? C6 C7 C8 C9 -0.2(4) . . . . ? C5 C4 C9 F5 -178.7(2) . . . . ? O1 C4 C9 F5 -6.8(3) . . . . ? C5 C4 C9 C8 0.4(3) . . . . ? O1 C4 C9 C8 172.2(2) . . . . ? F4 C8 C9 F5 -0.7(3) . . . . ? C7 C8 C9 F5 178.3(2) . . . . ? F4 C8 C9 C4 -179.7(2) . . . . ? C7 C8 C9 C4 -0.8(4) . . . . ? C2 O2 C10 C15 -112.3(2) . . . . ? C2 O2 C10 C11 73.7(3) . . . . ? C15 C10 C11 F6 -179.50(19) . . . . ? O2 C10 C11 F6 -5.6(3) . . . . ? C15 C10 C11 C12 0.5(3) . . . . ? O2 C10 C11 C12 174.42(19) . . . . ? F6 C11 C12 F7 0.5(3) . . . . ? C10 C11 C12 F7 -179.5(2) . . . . ? F6 C11 C12 C13 179.5(2) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? F7 C12 C13 F8 -1.9(3) . . . . ? C11 C12 C13 F8 179.2(2) . . . . ? F7 C12 C13 C14 179.4(2) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? F8 C13 C14 F9 0.1(3) . . . . ? C12 C13 C14 F9 178.8(2) . . . . ? F8 C13 C14 C15 -179.1(2) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C11 C10 C15 F10 178.59(19) . . . . ? O2 C10 C15 F10 4.4(3) . . . . ? C11 C10 C15 C14 -0.4(3) . . . . ? O2 C10 C15 C14 -174.55(19) . . . . ? F9 C14 C15 F10 2.2(3) . . . . ? C13 C14 C15 F10 -178.7(2) . . . . ? F9 C14 C15 C10 -178.8(2) . . . . ? C13 C14 C15 C10 0.3(3) . . . . ? C3 O3 C16 C17 -104.7(2) . . . . ? C3 O3 C16 C21 75.9(3) . . . . ? C21 C16 C17 F11 -178.87(18) . . . . ? O3 C16 C17 F11 1.7(3) . . . . ? C21 C16 C17 C18 0.6(3) . . . . ? O3 C16 C17 C18 -178.74(19) . . . . ? F11 C17 C18 F12 -1.7(3) . . . . ? C16 C17 C18 F12 178.83(19) . . . . ? F11 C17 C18 C19 179.33(19) . . . . ? C16 C17 C18 C19 -0.2(3) . . . . ? F12 C18 C19 F13 -0.9(3) . . . . ? C17 C18 C19 F13 178.2(2) . . . . ? F12 C18 C19 C20 -179.9(2) . . . . ? C17 C18 C19 C20 -0.9(3) . . . . ? F13 C19 C20 F14 1.7(3) . . . . ? C18 C19 C20 F14 -179.2(2) . . . . ? F13 C19 C20 C21 -177.6(2) . . . . ? C18 C19 C20 C21 1.5(3) . . . . ? F14 C20 C21 F15 1.8(3) . . . . ? C19 C20 C21 F15 -178.9(2) . . . . ? F14 C20 C21 C16 179.71(19) . . . . ? C19 C20 C21 C16 -1.0(3) . . . . ? C17 C16 C21 F15 177.82(19) . . . . ? O3 C16 C21 F15 -2.8(3) . . . . ? C17 C16 C21 C20 -0.1(3) . . . . ? O3 C16 C21 C20 179.32(19) . . . . ? C33 C31 C32 C33 0.0(4) . . . 2 ? C30 C31 C32 C33 -179.3(2) . . . 2 ? C32 C31 C33 C32 0.0(4) . . . 2 ? C30 C31 C33 C32 179.3(2) . . . 2 ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.90 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.413 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.053 data_kr-z1 _database_code_depnum_ccdc_archive 'CCDC 198643' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 Br3 F12 N3 O3' _chemical_formula_weight 809.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2648(6) _cell_length_b 17.8465(17) _cell_length_c 20.782(2) _cell_angle_alpha 86.114(12) _cell_angle_beta 84.699(12) _cell_angle_gamma 88.033(11) _cell_volume 2307.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 25.91 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 5.377 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.229 _exptl_absorpt_correction_T_max 0.692 _exptl_absorpt_process_details DIFABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18124 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.91 _reflns_number_total 8348 _reflns_number_gt 5835 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _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. ; _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^)+(0.0472P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8348 _refine_ls_number_parameters 757 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.04214(10) 0.78960(3) 0.30027(3) 0.03483(16) Uani 1 1 d . . . Br2 Br 0.20857(10) 0.48382(3) 0.08838(3) 0.03423(15) Uani 1 1 d . . . Br3 Br 1.49634(11) 0.81633(3) -0.31488(3) 0.03630(16) Uani 1 1 d . . . F1 F 0.6455(6) 0.93097(18) 0.21274(15) 0.0348(8) Uani 1 1 d . . . F2 F 0.3837(6) 0.8645(2) 0.30885(14) 0.0380(8) Uani 1 1 d . . . F3 F -0.0785(6) 0.80240(19) 0.15486(15) 0.0362(8) Uani 1 1 d . . . F4 F 0.1826(6) 0.86759(19) 0.05960(14) 0.0348(8) Uani 1 1 d . . . F5 F 0.8860(6) 0.64180(17) 0.09625(15) 0.0343(8) Uani 1 1 d . . . F6 F 0.6292(6) 0.52770(18) 0.13782(15) 0.0362(8) Uani 1 1 d . . . F7 F 0.1531(6) 0.60724(19) -0.01806(16) 0.0385(8) Uani 1 1 d . . . F8 F 0.4126(6) 0.72213(18) -0.05894(16) 0.0402(9) Uani 1 1 d . . . F9 F 0.8303(6) 0.96251(18) -0.21578(16) 0.0350(8) Uani 1 1 d . . . F10 F 1.0586(6) 0.89665(18) -0.31320(14) 0.0362(8) Uani 1 1 d . . . F11 F 1.6005(5) 0.82840(19) -0.17474(16) 0.0367(8) Uani 1 1 d . . . F12 F 1.3673(6) 0.89152(18) -0.07714(14) 0.0327(8) Uani 1 1 d . . . O1 O 0.5468(6) 0.94149(19) 0.08912(17) 0.0277(9) Uani 1 1 d . . . O2 O 0.8039(6) 0.73116(19) -0.01284(18) 0.0286(9) Uani 1 1 d . . . O3 O 0.9754(6) 0.96381(19) -0.09547(17) 0.0273(9) Uani 1 1 d . . . N1 N 0.7600(8) 0.9539(2) -0.0030(2) 0.0240(10) Uani 1 1 d . . . N2 N 0.6534(7) 0.8322(2) 0.04053(19) 0.0225(10) Uani 1 1 d . . . N3 N 0.8941(7) 0.8446(2) -0.0547(2) 0.0223(10) Uani 1 1 d . . . C1 C 0.6564(9) 0.9068(3) 0.0392(2) 0.0218(11) Uani 1 1 d . . . C2 C 0.7783(9) 0.8063(3) -0.0082(2) 0.0216(11) Uani 1 1 d . . . C3 C 0.8744(9) 0.9180(3) -0.0497(2) 0.0204(11) Uani 1 1 d . . . C4 C 0.4199(9) 0.9002(3) 0.1352(2) 0.0253(12) Uani 1 1 d . . . C5 C 0.4669(9) 0.8986(3) 0.1988(2) 0.0230(11) Uani 1 1 d . . . C6 C 0.3307(10) 0.8651(3) 0.2470(3) 0.0291(13) Uani 1 1 d . . . C7 C 0.1458(9) 0.8336(3) 0.2345(2) 0.0256(12) Uani 1 1 d . . . C8 C 0.1000(9) 0.8335(3) 0.1702(3) 0.0281(13) Uani 1 1 d . . . C9 C 0.2325(10) 0.8663(3) 0.1216(2) 0.0278(12) Uani 1 1 d . . . C10 C 0.6533(9) 0.6823(3) 0.0170(2) 0.0252(12) Uani 1 1 d . . . C11 C 0.7050(10) 0.6334(3) 0.0680(3) 0.0265(12) Uani 1 1 d . . . C12 C 0.5730(10) 0.5745(3) 0.0893(3) 0.0289(13) Uani 1 1 d . . . C13 C 0.3860(10) 0.5649(3) 0.0610(2) 0.0285(13) Uani 1 1 d . . . C14 C 0.3301(10) 0.6158(3) 0.0115(3) 0.0269(12) Uani 1 1 d . . . C15 C 0.4652(10) 0.6746(3) -0.0100(2) 0.0260(12) Uani 1 1 d . . . C16 C 1.0966(9) 0.9283(3) -0.1450(2) 0.0230(12) Uani 1 1 d . . . C17 C 1.0208(9) 0.9296(3) -0.2052(2) 0.0229(11) Uani 1 1 d . . . C18 C 1.1411(10) 0.8967(3) -0.2560(2) 0.0267(12) Uani 1 1 d . . . C19 C 1.3387(9) 0.8630(3) -0.2467(2) 0.0254(12) Uani 1 1 d . . . C20 C 1.4110(9) 0.8618(3) -0.1853(3) 0.0278(13) Uani 1 1 d . . . C21 C 1.2908(9) 0.8947(3) -0.1356(2) 0.0252(12) Uani 1 1 d . . . Br21 Br -0.55616(10) 0.31895(3) 0.77411(3) 0.03615(16) Uani 1 1 d . . . Br22 Br -0.29070(11) -0.00850(3) 0.59350(3) 0.03771(16) Uani 1 1 d . . . Br23 Br 0.99624(10) 0.29068(3) 0.16100(3) 0.03439(15) Uani 1 1 d . . . F21 F 0.1471(5) 0.44758(18) 0.68443(15) 0.0335(8) Uani 1 1 d . . . F22 F -0.1344(6) 0.3972(2) 0.78108(14) 0.0381(8) Uani 1 1 d . . . F23 F -0.5735(6) 0.31609(19) 0.62821(16) 0.0373(8) Uani 1 1 d . . . F24 F -0.2929(6) 0.36757(19) 0.53155(14) 0.0329(8) Uani 1 1 d . . . F25 F -0.0943(6) 0.20624(19) 0.41850(15) 0.0418(9) Uani 1 1 d . . . F26 F -0.3508(6) 0.0962(2) 0.47304(17) 0.0431(9) Uani 1 1 d . . . F27 F 0.1323(6) 0.04469(19) 0.63397(16) 0.0406(9) Uani 1 1 d . . . F28 F 0.3857(6) 0.15413(18) 0.57765(15) 0.0353(8) Uani 1 1 d . . . F29 F 0.3471(6) 0.44445(18) 0.26186(16) 0.0368(8) Uani 1 1 d . . . F30 F 0.5606(6) 0.37077(18) 0.16507(15) 0.0374(8) Uani 1 1 d . . . F31 F 1.1219(6) 0.30968(19) 0.29756(16) 0.0375(8) Uani 1 1 d . . . F32 F 0.9080(6) 0.38216(19) 0.39399(15) 0.0387(8) Uani 1 1 d . . . O21 O 0.0734(6) 0.44364(19) 0.55941(16) 0.0260(9) Uani 1 1 d . . . O22 O 0.2962(7) 0.2260(2) 0.46124(17) 0.0300(9) Uani 1 1 d . . . O23 O 0.5155(7) 0.4531(2) 0.37854(18) 0.0305(9) Uani 1 1 d . . . N21 N 0.2942(7) 0.4488(2) 0.4695(2) 0.0222(9) Uani 1 1 d . . . N22 N 0.1657(7) 0.3305(2) 0.5144(2) 0.0235(10) Uani 1 1 d . . . N23 N 0.4101(7) 0.3364(2) 0.4197(2) 0.0234(10) Uani 1 1 d . . . C22 C 0.1815(9) 0.4044(3) 0.5125(2) 0.0236(11) Uani 1 1 d . . . C23 C 0.2872(9) 0.3009(3) 0.4663(2) 0.0234(11) Uani 1 1 d . . . C24 C 0.4023(9) 0.4104(3) 0.4239(2) 0.0222(11) Uani 1 1 d . . . C25 C -0.0654(9) 0.4077(3) 0.6063(2) 0.0228(11) Uani 1 1 d . . . C26 C -0.2508(9) 0.3745(3) 0.5932(2) 0.0256(12) Uani 1 1 d . . . C27 C -0.3964(9) 0.3488(3) 0.6428(3) 0.0264(12) Uani 1 1 d . . . C28 C -0.3600(10) 0.3568(3) 0.7069(3) 0.0296(13) Uani 1 1 d . . . C29 C -0.1759(10) 0.3904(3) 0.7199(2) 0.0267(12) Uani 1 1 d . . . C30 C -0.0309(10) 0.4150(3) 0.6705(3) 0.0263(12) Uani 1 1 d . . . C31 C 0.1474(10) 0.1810(3) 0.4970(3) 0.0265(13) Uani 1 1 d . . . C32 C -0.0419(10) 0.1662(3) 0.4729(2) 0.0297(13) Uani 1 1 d . . . C33 C -0.1711(10) 0.1107(3) 0.5007(3) 0.0284(13) Uani 1 1 d . . . C34 C -0.1156(10) 0.0685(3) 0.5550(3) 0.0289(13) Uani 1 1 d . . . C35 C 0.0732(10) 0.0836(3) 0.5807(2) 0.0266(12) Uani 1 1 d . . . C36 C 0.2046(9) 0.1397(3) 0.5521(2) 0.0256(12) Uani 1 1 d . . . C37 C 0.6250(9) 0.4139(3) 0.3294(2) 0.0256(12) Uani 1 1 d . . . C38 C 0.8235(9) 0.3807(3) 0.3367(2) 0.0245(12) Uani 1 1 d . . . C39 C 0.9338(9) 0.3433(3) 0.2875(3) 0.0277(12) Uani 1 1 d . . . C40 C 0.8466(9) 0.3407(3) 0.2289(3) 0.0260(12) Uani 1 1 d . . . C41 C 0.6512(9) 0.3742(3) 0.2210(2) 0.0249(12) Uani 1 1 d . . . C42 C 0.5378(9) 0.4116(3) 0.2705(3) 0.0279(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0338(4) 0.0359(3) 0.0326(3) -0.0004(2) 0.0080(2) -0.0038(2) Br2 0.0313(4) 0.0270(3) 0.0440(3) -0.0007(2) -0.0001(3) -0.0065(2) Br3 0.0355(4) 0.0374(3) 0.0335(3) -0.0025(2) 0.0070(2) 0.0084(2) F1 0.030(2) 0.0405(18) 0.0351(17) -0.0056(14) -0.0031(14) -0.0083(15) F2 0.040(2) 0.053(2) 0.0222(16) -0.0035(14) -0.0046(14) -0.0108(16) F3 0.027(2) 0.048(2) 0.0344(18) -0.0031(15) -0.0029(14) -0.0101(15) F4 0.032(2) 0.050(2) 0.0235(16) -0.0040(14) -0.0044(13) -0.0048(15) F5 0.029(2) 0.0345(17) 0.0402(18) -0.0028(14) -0.0076(15) -0.0048(14) F6 0.039(2) 0.0313(17) 0.0379(18) 0.0111(14) -0.0100(15) -0.0017(14) F7 0.032(2) 0.045(2) 0.0401(19) -0.0008(15) -0.0113(15) -0.0013(15) F8 0.052(3) 0.0351(18) 0.0332(18) 0.0071(14) -0.0096(16) 0.0023(16) F9 0.027(2) 0.0362(17) 0.0412(18) -0.0034(14) -0.0045(14) 0.0106(14) F10 0.044(2) 0.0405(18) 0.0242(16) -0.0033(13) -0.0101(14) 0.0093(16) F11 0.017(2) 0.0445(19) 0.048(2) 0.0017(15) -0.0080(14) 0.0101(14) F12 0.033(2) 0.0387(18) 0.0276(16) 0.0001(13) -0.0115(14) -0.0017(14) O1 0.030(3) 0.0222(18) 0.0297(19) -0.0043(15) 0.0082(16) -0.0005(15) O2 0.029(3) 0.0186(17) 0.036(2) -0.0011(15) 0.0108(17) 0.0009(15) O3 0.032(3) 0.0212(18) 0.0271(19) -0.0032(14) 0.0065(16) -0.0009(15) N1 0.025(3) 0.023(2) 0.023(2) -0.0003(17) 0.0004(18) -0.0001(18) N2 0.021(3) 0.025(2) 0.022(2) -0.0010(17) -0.0036(18) -0.0002(18) N3 0.024(3) 0.019(2) 0.024(2) -0.0003(16) -0.0008(18) 0.0006(17) C1 0.016(3) 0.029(3) 0.021(2) 0.000(2) -0.009(2) 0.002(2) C2 0.015(3) 0.024(2) 0.026(3) -0.002(2) -0.008(2) 0.003(2) C3 0.020(3) 0.022(2) 0.020(2) 0.0004(19) -0.005(2) -0.001(2) C4 0.027(4) 0.020(2) 0.028(3) -0.003(2) 0.000(2) 0.002(2) C5 0.015(3) 0.027(3) 0.028(3) -0.008(2) -0.004(2) 0.001(2) C6 0.033(4) 0.029(3) 0.026(3) -0.004(2) -0.007(2) 0.003(2) C7 0.022(4) 0.029(3) 0.024(3) -0.001(2) 0.002(2) 0.004(2) C8 0.021(4) 0.036(3) 0.027(3) -0.005(2) 0.000(2) 0.002(2) C9 0.029(4) 0.034(3) 0.021(3) -0.006(2) -0.005(2) 0.005(2) C10 0.030(4) 0.020(2) 0.025(3) -0.004(2) 0.004(2) -0.003(2) C11 0.028(4) 0.024(3) 0.029(3) -0.006(2) -0.001(2) -0.001(2) C12 0.033(4) 0.029(3) 0.026(3) 0.002(2) -0.008(2) 0.003(2) C13 0.030(4) 0.031(3) 0.023(3) -0.002(2) 0.004(2) -0.004(2) C14 0.023(4) 0.029(3) 0.031(3) -0.004(2) -0.008(2) -0.002(2) C15 0.029(4) 0.023(3) 0.026(3) -0.002(2) -0.001(2) 0.002(2) C16 0.027(4) 0.018(2) 0.023(3) 0.0007(19) 0.001(2) -0.003(2) C17 0.018(3) 0.021(2) 0.029(3) 0.002(2) -0.004(2) 0.001(2) C18 0.028(4) 0.026(3) 0.026(3) -0.001(2) -0.003(2) -0.003(2) C19 0.021(4) 0.028(3) 0.026(3) 0.002(2) 0.000(2) 0.003(2) C20 0.021(4) 0.030(3) 0.031(3) 0.001(2) -0.001(2) -0.002(2) C21 0.023(4) 0.027(3) 0.025(3) 0.002(2) -0.005(2) -0.003(2) Br21 0.0324(4) 0.0423(3) 0.0320(3) -0.0021(2) 0.0077(2) -0.0048(3) Br22 0.0326(4) 0.0289(3) 0.0506(4) -0.0033(2) 0.0045(3) -0.0079(2) Br23 0.0341(4) 0.0349(3) 0.0323(3) -0.0043(2) 0.0052(2) 0.0066(2) F21 0.023(2) 0.0381(18) 0.0404(18) -0.0052(14) -0.0040(14) -0.0108(14) F22 0.039(2) 0.053(2) 0.0242(16) -0.0096(14) -0.0048(14) -0.0096(16) F23 0.024(2) 0.052(2) 0.0372(18) -0.0057(15) -0.0034(14) -0.0127(16) F24 0.028(2) 0.0479(19) 0.0242(16) -0.0062(14) -0.0061(13) -0.0007(15) F25 0.051(3) 0.045(2) 0.0299(18) 0.0045(15) -0.0126(16) 0.0040(17) F26 0.032(3) 0.053(2) 0.047(2) -0.0055(17) -0.0123(16) -0.0061(17) F27 0.040(3) 0.0374(19) 0.044(2) 0.0097(15) -0.0124(16) -0.0031(16) F28 0.029(2) 0.0426(19) 0.0357(18) -0.0055(14) -0.0046(15) -0.0060(15) F29 0.027(2) 0.0372(18) 0.0464(19) -0.0031(15) -0.0065(15) 0.0109(15) F30 0.045(3) 0.0372(18) 0.0327(18) -0.0058(14) -0.0173(15) 0.0087(15) F31 0.024(2) 0.0445(19) 0.0431(19) -0.0016(15) -0.0069(15) 0.0111(15) F32 0.039(2) 0.050(2) 0.0282(17) -0.0047(15) -0.0113(15) 0.0043(16) O21 0.030(2) 0.0215(17) 0.0247(18) -0.0006(14) 0.0081(16) 0.0012(15) O22 0.033(3) 0.0251(19) 0.031(2) -0.0048(15) 0.0075(17) -0.0036(16) O23 0.031(3) 0.0236(19) 0.035(2) -0.0007(15) 0.0086(17) -0.0004(16) N21 0.018(3) 0.021(2) 0.027(2) -0.0026(17) 0.0015(18) 0.0035(17) N22 0.021(3) 0.027(2) 0.023(2) -0.0038(17) -0.0026(18) 0.0013(18) N23 0.017(3) 0.026(2) 0.026(2) -0.0008(17) 0.0000(18) -0.0006(18) C22 0.018(3) 0.028(3) 0.025(3) -0.004(2) -0.003(2) 0.000(2) C23 0.015(3) 0.027(3) 0.029(3) -0.002(2) -0.006(2) 0.003(2) C24 0.013(3) 0.024(3) 0.030(3) 0.001(2) -0.004(2) -0.001(2) C25 0.019(3) 0.016(2) 0.033(3) -0.001(2) 0.002(2) 0.0033(19) C26 0.022(4) 0.029(3) 0.026(3) -0.004(2) -0.004(2) 0.006(2) C27 0.017(3) 0.029(3) 0.034(3) -0.003(2) -0.003(2) 0.002(2) C28 0.029(4) 0.029(3) 0.029(3) -0.003(2) 0.003(2) 0.005(2) C29 0.030(4) 0.027(3) 0.023(3) -0.007(2) -0.002(2) 0.002(2) C30 0.027(4) 0.023(3) 0.030(3) -0.008(2) -0.006(2) 0.004(2) C31 0.031(4) 0.016(2) 0.031(3) -0.004(2) 0.005(2) -0.003(2) C32 0.034(4) 0.032(3) 0.023(3) 0.002(2) -0.004(2) 0.004(2) C33 0.024(4) 0.030(3) 0.033(3) -0.010(2) -0.008(2) 0.001(2) C34 0.027(4) 0.028(3) 0.031(3) -0.004(2) 0.003(2) -0.001(2) C35 0.030(4) 0.025(3) 0.024(3) 0.003(2) -0.004(2) 0.000(2) C36 0.021(4) 0.029(3) 0.028(3) -0.008(2) -0.006(2) -0.003(2) C37 0.022(4) 0.028(3) 0.025(3) 0.000(2) 0.006(2) 0.004(2) C38 0.025(4) 0.029(3) 0.019(2) 0.000(2) -0.001(2) 0.000(2) C39 0.018(4) 0.034(3) 0.030(3) 0.005(2) -0.001(2) 0.002(2) C40 0.021(4) 0.026(3) 0.031(3) -0.003(2) -0.002(2) 0.002(2) C41 0.023(4) 0.031(3) 0.020(3) 0.001(2) -0.004(2) 0.000(2) C42 0.018(4) 0.028(3) 0.037(3) 0.003(2) -0.003(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C7 1.869(5) . ? Br2 C13 1.880(5) . ? Br3 C19 1.876(5) . ? F1 C5 1.341(6) . ? F2 C6 1.357(6) . ? F3 C8 1.339(7) . ? F4 C9 1.352(6) . ? F5 C11 1.342(7) . ? F6 C12 1.331(6) . ? F7 C14 1.334(7) . ? F8 C15 1.337(6) . ? F9 C17 1.342(6) . ? F10 C18 1.339(6) . ? F11 C20 1.340(7) . ? F12 C21 1.343(6) . ? O1 C1 1.362(6) . ? O1 C4 1.377(6) . ? O2 C2 1.355(6) . ? O2 C10 1.382(6) . ? O3 C3 1.338(6) . ? O3 C16 1.396(6) . ? N1 C1 1.315(7) . ? N1 C3 1.339(6) . ? N2 C2 1.321(6) . ? N2 C1 1.332(7) . ? N3 C2 1.318(7) . ? N3 C3 1.322(6) . ? C4 C5 1.378(8) . ? C4 C9 1.399(8) . ? C5 C6 1.373(8) . ? C6 C7 1.358(8) . ? C7 C8 1.392(8) . ? C8 C9 1.360(8) . ? C10 C15 1.366(8) . ? C10 C11 1.381(8) . ? C11 C12 1.383(8) . ? C12 C13 1.379(9) . ? C13 C14 1.388(8) . ? C14 C15 1.394(8) . ? C16 C21 1.362(8) . ? C16 C17 1.376(8) . ? C17 C18 1.392(7) . ? C18 C19 1.381(8) . ? C19 C20 1.391(8) . ? C20 C21 1.376(7) . ? Br21 C28 1.879(6) . ? Br22 C34 1.877(6) . ? Br23 C40 1.881(5) . ? F21 C30 1.339(7) . ? F22 C29 1.336(6) . ? F23 C27 1.339(7) . ? F24 C26 1.347(6) . ? F25 C32 1.356(6) . ? F26 C33 1.350(7) . ? F27 C35 1.340(6) . ? F28 C36 1.336(7) . ? F29 C42 1.334(7) . ? F30 C41 1.347(6) . ? F31 C39 1.332(7) . ? F32 C38 1.350(6) . ? O21 C22 1.356(6) . ? O21 C25 1.384(6) . ? O22 C23 1.347(6) . ? O22 C31 1.382(6) . ? O23 C24 1.337(6) . ? O23 C37 1.392(6) . ? N21 C22 1.323(7) . ? N21 C24 1.328(6) . ? N22 C22 1.323(7) . ? N22 C23 1.326(6) . ? N23 C23 1.321(7) . ? N23 C24 1.328(6) . ? C25 C26 1.378(8) . ? C25 C30 1.385(8) . ? C26 C27 1.376(8) . ? C27 C28 1.389(8) . ? C28 C29 1.375(8) . ? C29 C30 1.366(8) . ? C31 C32 1.370(9) . ? C31 C36 1.388(8) . ? C32 C33 1.365(8) . ? C33 C34 1.379(8) . ? C34 C35 1.384(8) . ? C35 C36 1.385(8) . ? C37 C38 1.376(8) . ? C37 C42 1.388(8) . ? C38 C39 1.377(7) . ? C39 C40 1.383(8) . ? C40 C41 1.362(8) . ? C41 C42 1.390(7) . ? 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 C1 O1 C4 119.9(4) . . ? C2 O2 C10 121.0(4) . . ? C3 O3 C16 115.5(4) . . ? C1 N1 C3 111.8(4) . . ? C2 N2 C1 111.0(4) . . ? C2 N3 C3 112.7(4) . . ? N1 C1 N2 129.0(5) . . ? N1 C1 O1 113.1(4) . . ? N2 C1 O1 117.9(4) . . ? N3 C2 N2 128.5(5) . . ? N3 C2 O2 112.2(4) . . ? N2 C2 O2 119.3(5) . . ? N3 C3 O3 119.0(4) . . ? N3 C3 N1 127.0(5) . . ? O3 C3 N1 113.9(4) . . ? O1 C4 C5 118.6(5) . . ? O1 C4 C9 122.9(5) . . ? C5 C4 C9 118.2(5) . . ? F1 C5 C6 120.7(5) . . ? F1 C5 C4 119.0(5) . . ? C6 C5 C4 120.2(5) . . ? F2 C6 C7 119.7(5) . . ? F2 C6 C5 118.2(5) . . ? C7 C6 C5 122.1(5) . . ? C6 C7 C8 118.0(5) . . ? C6 C7 Br1 122.1(4) . . ? C8 C7 Br1 120.0(4) . . ? F3 C8 C9 118.3(5) . . ? F3 C8 C7 120.7(5) . . ? C9 C8 C7 121.0(6) . . ? F4 C9 C8 120.3(5) . . ? F4 C9 C4 119.2(5) . . ? C8 C9 C4 120.5(5) . . ? C15 C10 C11 119.5(5) . . ? C15 C10 O2 119.6(5) . . ? C11 C10 O2 120.1(5) . . ? F5 C11 C10 120.1(5) . . ? F5 C11 C12 119.6(5) . . ? C10 C11 C12 120.3(6) . . ? F6 C12 C13 120.7(5) . . ? F6 C12 C11 118.7(5) . . ? C13 C12 C11 120.6(5) . . ? C12 C13 C14 119.1(5) . . ? C12 C13 Br2 120.9(4) . . ? C14 C13 Br2 120.0(5) . . ? F7 C14 C13 120.7(5) . . ? F7 C14 C15 119.3(5) . . ? C13 C14 C15 119.9(6) . . ? F8 C15 C10 120.0(5) . . ? F8 C15 C14 119.4(5) . . ? C10 C15 C14 120.6(5) . . ? C21 C16 C17 119.6(5) . . ? C21 C16 O3 121.4(5) . . ? C17 C16 O3 119.0(5) . . ? F9 C17 C16 120.7(5) . . ? F9 C17 C18 119.0(5) . . ? C16 C17 C18 120.3(5) . . ? F10 C18 C19 121.1(5) . . ? F10 C18 C17 118.6(5) . . ? C19 C18 C17 120.3(5) . . ? C18 C19 C20 118.3(5) . . ? C18 C19 Br3 120.0(4) . . ? C20 C19 Br3 121.6(4) . . ? F11 C20 C21 119.7(5) . . ? F11 C20 C19 119.6(5) . . ? C21 C20 C19 120.8(6) . . ? F12 C21 C16 120.9(5) . . ? F12 C21 C20 118.4(5) . . ? C16 C21 C20 120.7(5) . . ? C22 O21 C25 120.3(4) . . ? C23 O22 C31 120.2(4) . . ? C24 O23 C37 114.9(4) . . ? C22 N21 C24 112.0(4) . . ? C22 N22 C23 111.7(4) . . ? C23 N23 C24 112.7(4) . . ? N22 C22 N21 128.6(4) . . ? N22 C22 O21 119.6(5) . . ? N21 C22 O21 111.8(4) . . ? N23 C23 N22 127.8(5) . . ? N23 C23 O22 111.9(4) . . ? N22 C23 O22 120.2(5) . . ? N23 C24 N21 127.2(5) . . ? N23 C24 O23 118.6(4) . . ? N21 C24 O23 114.1(4) . . ? C26 C25 O21 123.7(5) . . ? C26 C25 C30 118.3(5) . . ? O21 C25 C30 117.4(5) . . ? F24 C26 C27 119.1(5) . . ? F24 C26 C25 120.3(5) . . ? C27 C26 C25 120.7(5) . . ? F23 C27 C26 119.0(5) . . ? F23 C27 C28 120.6(5) . . ? C26 C27 C28 120.4(6) . . ? C29 C28 C27 118.9(5) . . ? C29 C28 Br21 121.1(4) . . ? C27 C28 Br21 120.0(5) . . ? F22 C29 C30 119.5(5) . . ? F22 C29 C28 120.2(5) . . ? C30 C29 C28 120.3(5) . . ? F21 C30 C29 119.2(5) . . ? F21 C30 C25 119.4(5) . . ? C29 C30 C25 121.4(5) . . ? C32 C31 O22 120.5(5) . . ? C32 C31 C36 118.8(5) . . ? O22 C31 C36 119.7(5) . . ? F25 C32 C33 120.3(6) . . ? F25 C32 C31 118.2(5) . . ? C33 C32 C31 121.5(5) . . ? F26 C33 C32 118.9(5) . . ? F26 C33 C34 120.6(5) . . ? C32 C33 C34 120.5(6) . . ? C33 C34 C35 118.8(5) . . ? C33 C34 Br22 121.0(5) . . ? C35 C34 Br22 120.2(4) . . ? F27 C35 C34 120.9(5) . . ? F27 C35 C36 118.6(5) . . ? C34 C35 C36 120.5(5) . . ? F28 C36 C35 120.0(5) . . ? F28 C36 C31 120.1(5) . . ? C35 C36 C31 119.9(5) . . ? C38 C37 C42 119.1(5) . . ? C38 C37 O23 121.3(5) . . ? C42 C37 O23 119.5(5) . . ? F32 C38 C37 119.3(4) . . ? F32 C38 C39 119.3(5) . . ? C37 C38 C39 121.3(5) . . ? F31 C39 C38 119.1(5) . . ? F31 C39 C40 121.3(5) . . ? C38 C39 C40 119.6(5) . . ? C41 C40 C39 119.5(5) . . ? C41 C40 Br23 120.4(4) . . ? C39 C40 Br23 120.1(4) . . ? F30 C41 C40 120.6(5) . . ? F30 C41 C42 118.0(5) . . ? C40 C41 C42 121.4(5) . . ? F29 C42 C37 120.3(5) . . ? F29 C42 C41 120.6(5) . . ? C37 C42 C41 119.1(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 C3 N1 C1 N2 0.1(8) . . . . ? C3 N1 C1 O1 177.0(5) . . . . ? C2 N2 C1 N1 1.2(8) . . . . ? C2 N2 C1 O1 -175.5(5) . . . . ? C4 O1 C1 N1 176.1(5) . . . . ? C4 O1 C1 N2 -6.6(7) . . . . ? C3 N3 C2 N2 -0.8(8) . . . . ? C3 N3 C2 O2 -178.4(4) . . . . ? C1 N2 C2 N3 -0.8(8) . . . . ? C1 N2 C2 O2 176.6(5) . . . . ? C10 O2 C2 N3 -159.6(5) . . . . ? C10 O2 C2 N2 22.6(8) . . . . ? C2 N3 C3 O3 -176.8(5) . . . . ? C2 N3 C3 N1 2.5(8) . . . . ? C16 O3 C3 N3 -0.6(7) . . . . ? C16 O3 C3 N1 179.9(5) . . . . ? C1 N1 C3 N3 -2.2(8) . . . . ? C1 N1 C3 O3 177.2(5) . . . . ? C1 O1 C4 C5 119.6(5) . . . . ? C1 O1 C4 C9 -67.2(7) . . . . ? O1 C4 C5 F1 -6.3(7) . . . . ? C9 C4 C5 F1 -179.8(4) . . . . ? O1 C4 C5 C6 172.7(5) . . . . ? C9 C4 C5 C6 -0.8(8) . . . . ? F1 C5 C6 F2 -1.2(8) . . . . ? C4 C5 C6 F2 179.7(5) . . . . ? F1 C5 C6 C7 178.2(5) . . . . ? C4 C5 C6 C7 -0.8(8) . . . . ? F2 C6 C7 C8 -178.2(5) . . . . ? C5 C6 C7 C8 2.3(8) . . . . ? F2 C6 C7 Br1 0.6(7) . . . . ? C5 C6 C7 Br1 -178.8(4) . . . . ? C6 C7 C8 F3 179.2(5) . . . . ? Br1 C7 C8 F3 0.3(7) . . . . ? C6 C7 C8 C9 -2.3(8) . . . . ? Br1 C7 C8 C9 178.9(4) . . . . ? F3 C8 C9 F4 0.5(8) . . . . ? C7 C8 C9 F4 -178.1(5) . . . . ? F3 C8 C9 C4 179.3(5) . . . . ? C7 C8 C9 C4 0.7(8) . . . . ? O1 C4 C9 F4 6.4(8) . . . . ? C5 C4 C9 F4 179.6(5) . . . . ? O1 C4 C9 C8 -172.4(5) . . . . ? C5 C4 C9 C8 0.8(8) . . . . ? C2 O2 C10 C15 76.8(6) . . . . ? C2 O2 C10 C11 -113.0(6) . . . . ? C15 C10 C11 F5 -177.9(4) . . . . ? O2 C10 C11 F5 11.9(7) . . . . ? C15 C10 C11 C12 3.5(8) . . . . ? O2 C10 C11 C12 -166.7(5) . . . . ? F5 C11 C12 F6 0.4(7) . . . . ? C10 C11 C12 F6 179.0(4) . . . . ? F5 C11 C12 C13 179.8(4) . . . . ? C10 C11 C12 C13 -1.6(8) . . . . ? F6 C12 C13 C14 178.4(5) . . . . ? C11 C12 C13 C14 -1.0(8) . . . . ? F6 C12 C13 Br2 -1.8(7) . . . . ? C11 C12 C13 Br2 178.7(4) . . . . ? C12 C13 C14 F7 178.3(5) . . . . ? Br2 C13 C14 F7 -1.4(7) . . . . ? C12 C13 C14 C15 1.6(8) . . . . ? Br2 C13 C14 C15 -178.1(4) . . . . ? C11 C10 C15 F8 179.3(4) . . . . ? O2 C10 C15 F8 -10.4(7) . . . . ? C11 C10 C15 C14 -2.9(8) . . . . ? O2 C10 C15 C14 167.4(4) . . . . ? F7 C14 C15 F8 1.5(7) . . . . ? C13 C14 C15 F8 178.2(4) . . . . ? F7 C14 C15 C10 -176.4(4) . . . . ? C13 C14 C15 C10 0.3(8) . . . . ? C3 O3 C16 C21 -75.9(6) . . . . ? C3 O3 C16 C17 106.3(6) . . . . ? C21 C16 C17 F9 -179.8(5) . . . . ? O3 C16 C17 F9 -2.0(7) . . . . ? C21 C16 C17 C18 0.3(8) . . . . ? O3 C16 C17 C18 178.0(4) . . . . ? F9 C17 C18 F10 -2.4(7) . . . . ? C16 C17 C18 F10 177.6(5) . . . . ? F9 C17 C18 C19 179.4(5) . . . . ? C16 C17 C18 C19 -0.6(8) . . . . ? F10 C18 C19 C20 -177.0(5) . . . . ? C17 C18 C19 C20 1.2(8) . . . . ? F10 C18 C19 Br3 0.1(7) . . . . ? C17 C18 C19 Br3 178.3(4) . . . . ? C18 C19 C20 F11 178.9(5) . . . . ? Br3 C19 C20 F11 1.9(7) . . . . ? C18 C19 C20 C21 -1.4(8) . . . . ? Br3 C19 C20 C21 -178.4(4) . . . . ? C17 C16 C21 F12 -178.9(5) . . . . ? O3 C16 C21 F12 3.3(7) . . . . ? C17 C16 C21 C20 -0.5(8) . . . . ? O3 C16 C21 C20 -178.2(5) . . . . ? F11 C20 C21 F12 -0.8(7) . . . . ? C19 C20 C21 F12 179.5(5) . . . . ? F11 C20 C21 C16 -179.3(5) . . . . ? C19 C20 C21 C16 1.0(8) . . . . ? C23 N22 C22 N21 1.9(8) . . . . ? C23 N22 C22 O21 -177.8(5) . . . . ? C24 N21 C22 N22 -0.4(9) . . . . ? C24 N21 C22 O21 179.3(5) . . . . ? C25 O21 C22 N22 -4.8(8) . . . . ? C25 O21 C22 N21 175.5(5) . . . . ? C24 N23 C23 N22 -0.7(9) . . . . ? C24 N23 C23 O22 179.7(4) . . . . ? C22 N22 C23 N23 -1.3(8) . . . . ? C22 N22 C23 O22 178.3(5) . . . . ? C31 O22 C23 N23 -166.7(5) . . . . ? C31 O22 C23 N22 13.6(8) . . . . ? C23 N23 C24 N21 2.5(8) . . . . ? C23 N23 C24 O23 -178.4(5) . . . . ? C22 N21 C24 N23 -2.1(8) . . . . ? C22 N21 C24 O23 178.8(5) . . . . ? C37 O23 C24 N23 2.5(7) . . . . ? C37 O23 C24 N21 -178.3(5) . . . . ? C22 O21 C25 C26 -64.9(7) . . . . ? C22 O21 C25 C30 124.6(5) . . . . ? O21 C25 C26 F24 8.3(7) . . . . ? C30 C25 C26 F24 178.7(4) . . . . ? O21 C25 C26 C27 -171.0(5) . . . . ? C30 C25 C26 C27 -0.6(8) . . . . ? F24 C26 C27 F23 1.5(7) . . . . ? C25 C26 C27 F23 -179.2(5) . . . . ? F24 C26 C27 C28 -178.4(5) . . . . ? C25 C26 C27 C28 0.9(8) . . . . ? F23 C27 C28 C29 179.7(5) . . . . ? C26 C27 C28 C29 -0.3(8) . . . . ? F23 C27 C28 Br21 1.8(7) . . . . ? C26 C27 C28 Br21 -178.2(4) . . . . ? C27 C28 C29 F22 -178.3(5) . . . . ? Br21 C28 C29 F22 -0.5(7) . . . . ? C27 C28 C29 C30 -0.5(8) . . . . ? Br21 C28 C29 C30 177.4(4) . . . . ? F22 C29 C30 F21 -2.2(8) . . . . ? C28 C29 C30 F21 179.9(5) . . . . ? F22 C29 C30 C25 178.6(5) . . . . ? C28 C29 C30 C25 0.7(8) . . . . ? C26 C25 C30 F21 -179.4(4) . . . . ? O21 C25 C30 F21 -8.4(7) . . . . ? C26 C25 C30 C29 -0.2(8) . . . . ? O21 C25 C30 C29 170.8(5) . . . . ? C23 O22 C31 C32 89.1(6) . . . . ? C23 O22 C31 C36 -102.5(6) . . . . ? O22 C31 C32 F25 -10.6(7) . . . . ? C36 C31 C32 F25 -179.1(5) . . . . ? O22 C31 C32 C33 166.5(5) . . . . ? C36 C31 C32 C33 -2.0(8) . . . . ? F25 C32 C33 F26 0.1(8) . . . . ? C31 C32 C33 F26 -176.9(5) . . . . ? F25 C32 C33 C34 178.3(5) . . . . ? C31 C32 C33 C34 1.2(8) . . . . ? F26 C33 C34 C35 178.1(5) . . . . ? C32 C33 C34 C35 0.0(8) . . . . ? F26 C33 C34 Br22 -1.5(7) . . . . ? C32 C33 C34 Br22 -179.6(4) . . . . ? C33 C34 C35 F27 179.2(5) . . . . ? Br22 C34 C35 F27 -1.2(7) . . . . ? C33 C34 C35 C36 -0.4(8) . . . . ? Br22 C34 C35 C36 179.2(4) . . . . ? F27 C35 C36 F28 0.0(7) . . . . ? C34 C35 C36 F28 179.5(4) . . . . ? F27 C35 C36 C31 -179.9(4) . . . . ? C34 C35 C36 C31 -0.4(8) . . . . ? C32 C31 C36 F28 -178.4(5) . . . . ? O22 C31 C36 F28 13.0(7) . . . . ? C32 C31 C36 C35 1.5(7) . . . . ? O22 C31 C36 C35 -167.1(5) . . . . ? C24 O23 C37 C38 -84.1(6) . . . . ? C24 O23 C37 C42 99.4(6) . . . . ? C42 C37 C38 F32 -179.4(5) . . . . ? O23 C37 C38 F32 4.1(8) . . . . ? C42 C37 C38 C39 -2.0(8) . . . . ? O23 C37 C38 C39 -178.6(5) . . . . ? F32 C38 C39 F31 -0.2(8) . . . . ? C37 C38 C39 F31 -177.6(5) . . . . ? F32 C38 C39 C40 179.1(5) . . . . ? C37 C38 C39 C40 1.8(8) . . . . ? F31 C39 C40 C41 178.4(5) . . . . ? C38 C39 C40 C41 -0.9(8) . . . . ? F31 C39 C40 Br23 -1.3(7) . . . . ? C38 C39 C40 Br23 179.4(4) . . . . ? C39 C40 C41 F30 -178.3(5) . . . . ? Br23 C40 C41 F30 1.4(7) . . . . ? C39 C40 C41 C42 0.4(8) . . . . ? Br23 C40 C41 C42 -179.9(4) . . . . ? C38 C37 C42 F29 -178.9(5) . . . . ? O23 C37 C42 F29 -2.3(8) . . . . ? C38 C37 C42 C41 1.5(8) . . . . ? O23 C37 C42 C41 178.1(5) . . . . ? F30 C41 C42 F29 -1.6(8) . . . . ? C40 C41 C42 F29 179.6(5) . . . . ? F30 C41 C42 C37 178.0(5) . . . . ? C40 C41 C42 C37 -0.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.91 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.494 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.105 data_z3sub _database_code_depnum_ccdc_archive 'CCDC 198644' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H0 F15 N3 O3' _chemical_formula_weight 627.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.9960(5) _cell_length_b 26.5650(15) _cell_length_c 13.5330(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.315(9) _cell_angle_gamma 90.00 _cell_volume 2127.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 25.92 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.220 _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 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16928 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0616 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.92 _reflns_number_total 8089 _reflns_number_gt 6509 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _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. ; _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^)+(0.0462P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0005(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(4) _refine_ls_number_reflns 8089 _refine_ls_number_parameters 759 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _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 -0.3714(3) -0.30098(8) -0.02360(14) 0.0476(5) Uani 1 1 d . . . F2 F -0.2002(5) -0.22223(9) 0.09398(18) 0.0692(7) Uani 1 1 d . . . F3 F 0.2366(5) -0.22607(9) 0.18982(16) 0.0681(7) Uani 1 1 d . . . F4 F 0.4983(3) -0.30660(10) 0.16766(14) 0.0604(6) Uani 1 1 d . . . F5 F 0.3274(3) -0.38301(8) 0.04472(14) 0.0482(5) Uani 1 1 d . . . F6 F -0.7441(3) -0.44579(7) -0.23352(12) 0.0359(4) Uani 1 1 d . . . F7 F -0.9040(3) -0.51709(8) -0.12220(13) 0.0462(5) Uani 1 1 d . . . F8 F -0.7038(4) -0.60902(8) -0.10140(15) 0.0599(6) Uani 1 1 d . . . F9 F -0.3330(4) -0.62818(7) -0.18802(15) 0.0530(5) Uani 1 1 d . . . F10 F -0.1741(3) -0.55648(7) -0.30169(12) 0.0366(4) Uani 1 1 d . . . F11 F -0.2872(3) -0.22835(7) -0.34782(13) 0.0382(4) Uani 1 1 d . . . F12 F -0.1089(4) -0.14231(8) -0.26156(15) 0.0532(5) Uani 1 1 d . . . F13 F 0.3263(4) -0.14063(8) -0.16781(16) 0.0575(5) Uani 1 1 d . . . F14 F 0.5830(3) -0.22481(8) -0.15861(14) 0.0482(5) Uani 1 1 d . . . F15 F 0.4016(3) -0.31190(8) -0.24382(13) 0.0413(4) Uani 1 1 d . . . O1 O -0.1140(3) -0.38424(8) -0.04187(13) 0.0314(5) Uani 1 1 d . . . O2 O -0.3768(3) -0.46463(7) -0.33103(13) 0.0257(4) Uani 1 1 d . . . O3 O -0.0398(3) -0.31406(7) -0.34597(13) 0.0280(4) Uani 1 1 d . . . N1 N -0.0678(4) -0.34524(8) -0.19004(16) 0.0216(5) Uani 1 1 d . . . N2 N -0.2471(4) -0.42451(9) -0.18304(15) 0.0227(5) Uani 1 1 d . . . N3 N -0.2088(4) -0.38932(8) -0.34107(15) 0.0226(5) Uani 1 1 d . . . C1 C -0.1427(4) -0.38413(11) -0.14311(18) 0.0214(5) Uani 1 1 d . . . C2 C -0.2734(4) -0.42426(10) -0.28217(18) 0.0209(5) Uani 1 1 d . . . C3 C -0.1077(4) -0.35110(10) -0.28927(18) 0.0211(5) Uani 1 1 d . . . C4 C -0.0218(5) -0.34167(11) 0.00892(19) 0.0265(6) Uani 1 1 d . . . C5 C -0.1565(5) -0.30111(12) 0.0213(2) 0.0332(7) Uani 1 1 d . . . C6 C -0.0688(6) -0.26152(13) 0.0817(2) 0.0419(8) Uani 1 1 d . . . C7 C 0.1536(6) -0.26401(14) 0.1297(2) 0.0443(9) Uani 1 1 d . . . C8 C 0.2881(5) -0.30458(14) 0.1180(2) 0.0387(8) Uani 1 1 d . . . C9 C 0.1984(5) -0.34333(12) 0.0566(2) 0.0316(7) Uani 1 1 d . . . C10 C -0.4590(4) -0.50054(10) -0.27123(18) 0.0220(5) Uani 1 1 d . . . C11 C -0.6453(4) -0.49111(11) -0.2256(2) 0.0256(6) Uani 1 1 d . . . C12 C -0.7257(5) -0.52766(12) -0.1680(2) 0.0318(7) Uani 1 1 d . . . C13 C -0.6245(6) -0.57384(13) -0.1570(2) 0.0364(7) Uani 1 1 d . . . C14 C -0.4368(6) -0.58339(11) -0.2014(2) 0.0343(7) Uani 1 1 d . . . C15 C -0.3563(4) -0.54689(11) -0.25887(19) 0.0261(6) Uani 1 1 d . . . C16 C 0.0546(5) -0.27131(10) -0.29616(19) 0.0240(6) Uani 1 1 d . . . C17 C -0.0737(4) -0.22803(12) -0.3008(2) 0.0286(6) Uani 1 1 d . . . C18 C 0.0162(5) -0.18438(12) -0.2562(2) 0.0345(7) Uani 1 1 d . . . C19 C 0.2362(6) -0.18353(12) -0.2083(2) 0.0359(7) Uani 1 1 d . . . C20 C 0.3663(5) -0.22640(13) -0.2041(2) 0.0358(7) Uani 1 1 d . . . C21 C 0.2749(5) -0.27026(11) -0.2481(2) 0.0290(6) Uani 1 1 d . . . F16 F -0.2212(3) -0.34264(6) -0.57620(13) 0.0339(4) Uani 1 1 d . . . F17 F -0.0468(3) -0.26929(7) -0.67922(13) 0.0387(4) Uani 1 1 d . . . F18 F -0.2285(3) -0.17547(7) -0.69041(13) 0.0438(5) Uani 1 1 d . . . F19 F -0.5954(3) -0.15564(6) -0.60054(13) 0.0415(5) Uani 1 1 d . . . F20 F -0.7753(3) -0.22984(6) -0.49970(12) 0.0313(4) Uani 1 1 d . . . F21 F -1.3801(3) -0.46425(6) -0.55809(12) 0.0321(4) Uani 1 1 d . . . F22 F -1.6059(2) -0.54993(7) -0.62703(12) 0.0342(4) Uani 1 1 d . . . F23 F -1.3912(3) -0.63906(7) -0.61113(12) 0.0359(4) Uani 1 1 d . . . F24 F -0.9490(3) -0.64508(6) -0.52073(13) 0.0357(4) Uani 1 1 d . . . F25 F -0.7327(2) -0.56125(6) -0.44361(11) 0.0299(4) Uani 1 1 d . . . F26 F -1.2709(3) -0.41489(7) -0.85146(13) 0.0423(4) Uani 1 1 d . . . F27 F -1.4245(3) -0.49486(9) -0.96815(14) 0.0522(6) Uani 1 1 d . . . F28 F -1.1480(4) -0.57427(8) -0.98218(15) 0.0562(6) Uani 1 1 d . . . F29 F -0.7123(4) -0.57265(8) -0.88586(16) 0.0543(5) Uani 1 1 d . . . F30 F -0.5553(3) -0.49010(7) -0.77709(13) 0.0397(4) Uani 1 1 d . . . O4 O -0.5885(3) -0.32245(7) -0.47766(13) 0.0250(4) Uani 1 1 d . . . O5 O -0.9391(3) -0.46996(7) -0.45542(13) 0.0239(4) Uani 1 1 d . . . O6 O -0.8298(3) -0.40899(8) -0.76267(13) 0.0299(4) Uani 1 1 d . . . N4 N -0.7092(4) -0.36470(8) -0.62404(15) 0.0216(5) Uani 1 1 d . . . N5 N -0.7629(4) -0.39634(8) -0.46502(16) 0.0219(5) Uani 1 1 d . . . N6 N -0.8991(4) -0.44276(8) -0.61351(15) 0.0208(5) Uani 1 1 d . . . C22 C -0.6916(4) -0.36304(10) -0.52570(19) 0.0211(5) Uani 1 1 d . . . C23 C -0.8647(4) -0.43457(10) -0.51480(18) 0.0197(5) Uani 1 1 d . . . C24 C -0.8130(4) -0.40611(11) -0.66225(18) 0.0216(5) Uani 1 1 d . . . C25 C -0.5004(4) -0.28701(10) -0.53643(18) 0.0219(5) Uani 1 1 d . . . C26 C -0.3135(4) -0.29658(11) -0.5817(2) 0.0261(6) Uani 1 1 d . . . C27 C -0.2256(4) -0.25896(11) -0.6344(2) 0.0275(6) Uani 1 1 d . . . C28 C -0.3187(5) -0.21192(11) -0.6404(2) 0.0289(6) Uani 1 1 d . . . C29 C -0.5032(5) -0.20159(11) -0.5948(2) 0.0271(6) Uani 1 1 d . . . C30 C -0.5935(4) -0.23954(11) -0.54344(19) 0.0236(6) Uani 1 1 d . . . C31 C -1.0521(4) -0.51144(10) -0.50117(18) 0.0217(6) Uani 1 1 d . . . C32 C -1.2749(4) -0.50898(10) -0.54841(19) 0.0235(6) Uani 1 1 d . . . C33 C -1.3889(4) -0.55165(11) -0.58460(19) 0.0253(6) Uani 1 1 d . . . C34 C -1.2788(5) -0.59780(11) -0.5758(2) 0.0263(6) Uani 1 1 d . . . C35 C -1.0563(5) -0.60066(11) -0.5291(2) 0.0251(6) Uani 1 1 d . . . C36 C -0.9458(4) -0.55788(10) -0.49108(18) 0.0209(5) Uani 1 1 d . . . C37 C -0.9136(5) -0.45256(11) -0.81125(18) 0.0245(6) Uani 1 1 d . . . C38 C -1.1331(5) -0.45414(12) -0.8597(2) 0.0298(6) Uani 1 1 d . . . C39 C -1.2114(5) -0.49458(13) -0.9183(2) 0.0342(7) Uani 1 1 d . . . C40 C -1.0700(6) -0.53482(12) -0.9256(2) 0.0350(7) Uani 1 1 d . . . C41 C -0.8500(6) -0.53415(12) -0.8771(2) 0.0344(7) Uani 1 1 d . . . C42 C -0.7715(5) -0.49240(11) -0.8209(2) 0.0276(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0426(10) 0.0592(14) 0.0401(10) 0.0038(9) 0.0037(8) 0.0041(9) F2 0.1052(18) 0.0391(14) 0.0676(15) -0.0098(11) 0.0270(13) 0.0153(12) F3 0.1064(18) 0.0528(15) 0.0466(12) -0.0234(10) 0.0168(12) -0.0455(13) F4 0.0454(11) 0.0947(19) 0.0371(10) -0.0018(11) -0.0053(8) -0.0273(11) F5 0.0454(11) 0.0563(13) 0.0421(10) 0.0008(9) 0.0049(8) 0.0088(10) F6 0.0357(9) 0.0373(11) 0.0358(9) 0.0015(7) 0.0093(7) 0.0100(8) F7 0.0376(10) 0.0635(14) 0.0420(11) -0.0039(9) 0.0197(8) -0.0112(9) F8 0.0956(16) 0.0430(13) 0.0470(12) 0.0070(10) 0.0292(11) -0.0237(11) F9 0.0915(15) 0.0245(11) 0.0429(11) 0.0066(8) 0.0113(10) 0.0129(10) F10 0.0409(9) 0.0372(11) 0.0334(9) -0.0022(8) 0.0115(7) 0.0111(8) F11 0.0334(9) 0.0425(12) 0.0363(9) -0.0031(8) -0.0013(7) 0.0055(8) F12 0.0705(13) 0.0305(11) 0.0561(12) -0.0091(9) 0.0032(10) 0.0116(10) F13 0.0758(14) 0.0406(12) 0.0554(12) -0.0159(9) 0.0082(10) -0.0276(11) F14 0.0336(9) 0.0654(14) 0.0426(11) 0.0006(10) -0.0023(8) -0.0146(9) F15 0.0373(9) 0.0457(11) 0.0401(10) 0.0036(8) 0.0038(7) 0.0102(8) O1 0.0504(12) 0.0288(11) 0.0148(9) -0.0019(8) 0.0046(8) -0.0141(9) O2 0.0346(10) 0.0232(11) 0.0201(9) -0.0023(8) 0.0067(8) -0.0068(8) O3 0.0399(11) 0.0240(11) 0.0210(9) -0.0003(8) 0.0076(8) -0.0068(9) N1 0.0280(11) 0.0184(12) 0.0190(11) 0.0005(8) 0.0052(8) -0.0009(9) N2 0.0266(11) 0.0222(13) 0.0198(11) 0.0010(9) 0.0053(9) -0.0026(9) N3 0.0273(11) 0.0203(12) 0.0207(11) -0.0002(9) 0.0056(9) 0.0010(9) C1 0.0230(12) 0.0254(15) 0.0155(12) -0.0012(10) 0.0025(9) 0.0003(11) C2 0.0227(12) 0.0212(15) 0.0190(12) -0.0032(10) 0.0043(10) 0.0018(10) C3 0.0230(12) 0.0207(15) 0.0202(13) 0.0035(10) 0.0053(10) 0.0038(10) C4 0.0384(15) 0.0260(16) 0.0154(12) -0.0013(10) 0.0052(10) -0.0083(12) C5 0.0361(16) 0.0377(19) 0.0257(14) 0.0035(12) 0.0042(12) -0.0019(13) C6 0.069(2) 0.0263(18) 0.0346(17) -0.0017(13) 0.0206(16) 0.0010(16) C7 0.070(2) 0.040(2) 0.0233(15) -0.0097(13) 0.0099(15) -0.0301(18) C8 0.0414(17) 0.051(2) 0.0236(14) -0.0074(14) 0.0059(12) -0.0195(16) C9 0.0354(15) 0.0370(19) 0.0229(14) -0.0003(12) 0.0061(11) -0.0094(14) C10 0.0265(13) 0.0223(15) 0.0169(12) -0.0007(10) 0.0029(10) -0.0062(11) C11 0.0232(13) 0.0295(17) 0.0232(13) -0.0029(11) 0.0009(10) -0.0039(12) C12 0.0304(15) 0.041(2) 0.0246(14) -0.0036(13) 0.0071(11) -0.0111(13) C13 0.0508(18) 0.0341(19) 0.0242(14) 0.0014(12) 0.0062(13) -0.0170(15) C14 0.0563(19) 0.0184(17) 0.0273(15) -0.0013(11) 0.0036(13) 0.0015(13) C15 0.0293(14) 0.0284(16) 0.0208(13) -0.0041(11) 0.0050(10) -0.0016(12) C16 0.0338(14) 0.0196(15) 0.0198(13) 0.0023(11) 0.0074(11) -0.0056(11) C17 0.0279(14) 0.0347(18) 0.0231(13) 0.0029(12) 0.0035(11) 0.0003(12) C18 0.0464(18) 0.0232(17) 0.0347(16) -0.0032(12) 0.0091(13) -0.0009(13) C19 0.0471(18) 0.0279(18) 0.0327(15) -0.0049(12) 0.0069(13) -0.0123(14) C20 0.0305(14) 0.047(2) 0.0293(15) 0.0016(13) 0.0039(12) -0.0125(14) C21 0.0337(15) 0.0280(17) 0.0268(14) 0.0043(12) 0.0092(11) 0.0028(12) F16 0.0322(9) 0.0298(10) 0.0399(10) 0.0002(7) 0.0067(7) 0.0103(7) F17 0.0302(9) 0.0506(12) 0.0383(10) -0.0013(8) 0.0145(7) -0.0010(8) F18 0.0594(12) 0.0363(11) 0.0388(10) 0.0087(8) 0.0177(8) -0.0134(9) F19 0.0653(12) 0.0204(10) 0.0411(10) 0.0061(7) 0.0156(9) 0.0097(8) F20 0.0332(8) 0.0286(9) 0.0347(9) -0.0054(7) 0.0132(7) 0.0027(7) F21 0.0355(9) 0.0263(10) 0.0349(9) 0.0011(7) 0.0066(7) 0.0106(7) F22 0.0227(8) 0.0447(11) 0.0341(9) 0.0048(7) 0.0016(6) -0.0014(7) F23 0.0402(9) 0.0272(10) 0.0376(9) -0.0034(7) -0.0015(7) -0.0114(7) F24 0.0433(9) 0.0190(9) 0.0425(10) -0.0015(7) 0.0002(7) 0.0062(7) F25 0.0247(8) 0.0324(10) 0.0301(8) 0.0002(7) -0.0027(6) 0.0001(7) F26 0.0398(10) 0.0465(12) 0.0416(10) 0.0046(8) 0.0097(8) 0.0083(9) F27 0.0354(10) 0.0862(17) 0.0331(10) -0.0086(10) -0.0007(7) -0.0208(10) F28 0.0789(14) 0.0503(13) 0.0432(11) -0.0226(9) 0.0217(10) -0.0326(11) F29 0.0736(14) 0.0354(12) 0.0595(13) -0.0042(9) 0.0281(11) 0.0091(10) F30 0.0297(9) 0.0538(13) 0.0345(9) 0.0075(8) 0.0019(7) -0.0014(8) O4 0.0346(10) 0.0177(10) 0.0234(9) -0.0011(7) 0.0068(8) -0.0053(8) O5 0.0366(10) 0.0183(11) 0.0173(9) 0.0002(7) 0.0056(7) -0.0065(8) O6 0.0460(12) 0.0262(11) 0.0179(9) -0.0007(8) 0.0061(8) -0.0109(9) N4 0.0255(11) 0.0190(12) 0.0202(11) 0.0004(9) 0.0035(9) -0.0028(9) N5 0.0261(11) 0.0186(12) 0.0210(11) 0.0003(8) 0.0035(8) -0.0018(9) N6 0.0244(11) 0.0198(13) 0.0187(10) 0.0010(8) 0.0056(8) -0.0012(9) C22 0.0209(12) 0.0166(14) 0.0258(13) -0.0026(10) 0.0042(10) -0.0014(10) C23 0.0216(12) 0.0162(14) 0.0218(12) 0.0006(10) 0.0049(9) 0.0022(10) C24 0.0223(12) 0.0238(15) 0.0191(12) -0.0005(10) 0.0049(9) -0.0015(11) C25 0.0265(12) 0.0188(15) 0.0201(12) -0.0014(10) 0.0026(10) -0.0051(11) C26 0.0281(14) 0.0241(16) 0.0257(13) -0.0031(11) 0.0031(10) 0.0009(12) C27 0.0221(13) 0.0364(18) 0.0249(14) -0.0043(12) 0.0065(11) -0.0033(12) C28 0.0368(15) 0.0271(17) 0.0231(13) 0.0015(11) 0.0059(11) -0.0100(12) C29 0.0376(15) 0.0191(16) 0.0239(13) -0.0021(11) 0.0031(11) -0.0016(12) C30 0.0280(13) 0.0226(15) 0.0204(13) -0.0015(10) 0.0045(10) 0.0008(11) C31 0.0313(14) 0.0196(15) 0.0155(12) 0.0006(10) 0.0075(10) -0.0042(11) C32 0.0257(13) 0.0215(15) 0.0248(13) 0.0048(10) 0.0086(10) 0.0040(11) C33 0.0228(13) 0.0335(17) 0.0200(12) 0.0042(11) 0.0048(10) 0.0010(11) C34 0.0326(14) 0.0202(15) 0.0259(14) -0.0009(11) 0.0037(11) -0.0072(12) C35 0.0327(14) 0.0182(14) 0.0245(13) 0.0022(10) 0.0048(11) 0.0015(11) C36 0.0213(12) 0.0216(15) 0.0200(12) 0.0012(10) 0.0040(10) -0.0016(10) C37 0.0310(14) 0.0285(16) 0.0144(11) -0.0007(10) 0.0045(10) -0.0093(11) C38 0.0333(15) 0.0322(17) 0.0255(14) 0.0051(12) 0.0095(11) 0.0021(12) C39 0.0323(15) 0.050(2) 0.0211(14) -0.0034(13) 0.0061(11) -0.0135(14) C40 0.0508(19) 0.0339(19) 0.0225(14) -0.0097(13) 0.0121(13) -0.0160(14) C41 0.0465(17) 0.0296(18) 0.0298(15) -0.0012(13) 0.0145(13) -0.0015(14) C42 0.0294(14) 0.0330(17) 0.0207(13) 0.0028(12) 0.0052(10) -0.0044(12) _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 C5 1.332(3) . ? F2 C6 1.334(4) . ? F3 C7 1.340(4) . ? F4 C8 1.330(4) . ? F5 C9 1.333(4) . ? F6 C11 1.338(3) . ? F7 C12 1.349(3) . ? F8 C13 1.334(4) . ? F9 C14 1.341(4) . ? F10 C15 1.341(3) . ? F11 C17 1.334(3) . ? F12 C18 1.341(4) . ? F13 C19 1.340(4) . ? F14 C20 1.345(3) . ? F15 C21 1.338(3) . ? O1 C1 1.353(3) . ? O1 C4 1.391(3) . ? O2 C2 1.356(3) . ? O2 C10 1.392(3) . ? O3 C3 1.350(3) . ? O3 C16 1.393(3) . ? N1 C1 1.328(3) . ? N1 C3 1.335(3) . ? N2 C1 1.313(3) . ? N2 C2 1.325(3) . ? N3 C2 1.322(3) . ? N3 C3 1.324(3) . ? C4 C5 1.373(4) . ? C4 C9 1.373(4) . ? C5 C6 1.383(5) . ? C6 C7 1.387(5) . ? C7 C8 1.370(5) . ? C8 C9 1.377(4) . ? C10 C15 1.375(4) . ? C10 C11 1.384(4) . ? C11 C12 1.380(4) . ? C12 C13 1.366(5) . ? C13 C14 1.382(5) . ? C14 C15 1.378(4) . ? C16 C21 1.375(4) . ? C16 C17 1.379(4) . ? C17 C18 1.376(4) . ? C18 C19 1.372(5) . ? C19 C20 1.376(5) . ? C20 C21 1.381(4) . ? F16 C26 1.340(3) . ? F17 C27 1.343(3) . ? F18 C28 1.344(3) . ? F19 C29 1.337(3) . ? F20 C30 1.347(3) . ? F21 C32 1.342(3) . ? F22 C33 1.335(3) . ? F23 C34 1.334(3) . ? F24 C35 1.340(3) . ? F25 C36 1.337(3) . ? F26 C38 1.346(4) . ? F27 C39 1.344(4) . ? F28 C40 1.337(3) . ? F29 C41 1.331(4) . ? F30 C42 1.337(3) . ? O4 C22 1.355(3) . ? O4 C25 1.391(3) . ? O5 C23 1.358(3) . ? O5 C31 1.386(3) . ? O6 C24 1.348(3) . ? O6 C37 1.385(3) . ? N4 C22 1.319(3) . ? N4 C24 1.327(3) . ? N5 C23 1.313(3) . ? N5 C22 1.324(3) . ? N6 C24 1.327(3) . ? N6 C23 1.336(3) . ? C25 C30 1.376(4) . ? C25 C26 1.385(4) . ? C26 C27 1.381(4) . ? C27 C28 1.366(4) . ? C28 C29 1.379(4) . ? C29 C30 1.383(4) . ? C31 C36 1.385(4) . ? C31 C32 1.386(4) . ? C32 C33 1.373(4) . ? C33 C34 1.388(4) . ? C34 C35 1.383(4) . ? C35 C36 1.373(4) . ? C37 C38 1.372(4) . ? C37 C42 1.378(4) . ? C38 C39 1.373(4) . ? C39 C40 1.378(5) . ? C40 C41 1.375(5) . ? C41 C42 1.383(4) . ? 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 C1 O1 C4 118.3(2) . . ? C2 O2 C10 115.82(19) . . ? C3 O3 C16 117.1(2) . . ? C1 N1 C3 111.8(2) . . ? C1 N2 C2 112.5(2) . . ? C2 N3 C3 111.9(2) . . ? N2 C1 N1 127.9(2) . . ? N2 C1 O1 112.9(2) . . ? N1 C1 O1 119.2(2) . . ? N3 C2 N2 128.0(2) . . ? N3 C2 O2 114.6(2) . . ? N2 C2 O2 117.4(2) . . ? N3 C3 N1 127.9(2) . . ? N3 C3 O3 114.4(2) . . ? N1 C3 O3 117.7(2) . . ? C5 C4 C9 120.5(3) . . ? C5 C4 O1 120.2(3) . . ? C9 C4 O1 118.8(3) . . ? F1 C5 C4 119.4(3) . . ? F1 C5 C6 121.0(3) . . ? C4 C5 C6 119.6(3) . . ? F2 C6 C5 119.6(3) . . ? F2 C6 C7 121.4(3) . . ? C5 C6 C7 119.0(3) . . ? F3 C7 C8 119.6(3) . . ? F3 C7 C6 118.9(4) . . ? C8 C7 C6 121.5(3) . . ? F4 C8 C7 120.1(3) . . ? F4 C8 C9 121.4(3) . . ? C7 C8 C9 118.5(3) . . ? F5 C9 C4 120.1(3) . . ? F5 C9 C8 119.1(3) . . ? C4 C9 C8 120.8(3) . . ? C15 C10 C11 119.1(2) . . ? C15 C10 O2 119.4(2) . . ? C11 C10 O2 121.5(3) . . ? F6 C11 C12 119.2(2) . . ? F6 C11 C10 120.4(2) . . ? C12 C11 C10 120.4(3) . . ? F7 C12 C13 120.5(3) . . ? F7 C12 C11 119.2(3) . . ? C13 C12 C11 120.3(3) . . ? F8 C13 C12 119.9(3) . . ? F8 C13 C14 120.4(3) . . ? C12 C13 C14 119.7(3) . . ? F9 C14 C15 120.2(3) . . ? F9 C14 C13 119.8(3) . . ? C15 C14 C13 120.0(3) . . ? F10 C15 C10 119.8(2) . . ? F10 C15 C14 119.6(3) . . ? C10 C15 C14 120.5(3) . . ? C21 C16 C17 119.4(3) . . ? C21 C16 O3 122.0(3) . . ? C17 C16 O3 118.5(2) . . ? F11 C17 C18 119.5(3) . . ? F11 C17 C16 120.1(3) . . ? C18 C17 C16 120.4(3) . . ? F12 C18 C19 119.9(3) . . ? F12 C18 C17 120.1(3) . . ? C19 C18 C17 119.9(3) . . ? F13 C19 C18 120.0(3) . . ? F13 C19 C20 119.9(3) . . ? C18 C19 C20 120.1(3) . . ? F14 C20 C19 119.5(3) . . ? F14 C20 C21 120.7(3) . . ? C19 C20 C21 119.8(3) . . ? F15 C21 C16 119.9(3) . . ? F15 C21 C20 119.7(3) . . ? C16 C21 C20 120.3(3) . . ? C22 O4 C25 116.75(19) . . ? C23 O5 C31 118.01(19) . . ? C24 O6 C37 119.2(2) . . ? C22 N4 C24 112.1(2) . . ? C23 N5 C22 111.6(2) . . ? C24 N6 C23 111.6(2) . . ? N4 C22 N5 128.5(2) . . ? N4 C22 O4 117.8(2) . . ? N5 C22 O4 113.7(2) . . ? N5 C23 N6 128.5(2) . . ? N5 C23 O5 113.7(2) . . ? N6 C23 O5 117.8(2) . . ? N6 C24 N4 127.6(2) . . ? N6 C24 O6 119.2(2) . . ? N4 C24 O6 113.2(2) . . ? C30 C25 C26 119.1(2) . . ? C30 C25 O4 118.2(2) . . ? C26 C25 O4 122.5(2) . . ? F16 C26 C27 120.0(2) . . ? F16 C26 C25 120.0(2) . . ? C27 C26 C25 120.0(3) . . ? F17 C27 C28 120.6(3) . . ? F17 C27 C26 119.0(3) . . ? C28 C27 C26 120.4(2) . . ? F18 C28 C27 119.7(3) . . ? F18 C28 C29 120.0(3) . . ? C27 C28 C29 120.3(3) . . ? F19 C29 C28 120.6(3) . . ? F19 C29 C30 120.2(3) . . ? C28 C29 C30 119.2(3) . . ? F20 C30 C25 119.5(2) . . ? F20 C30 C29 119.4(2) . . ? C25 C30 C29 121.0(2) . . ? C36 C31 O5 118.7(2) . . ? C36 C31 C32 118.8(2) . . ? O5 C31 C32 122.2(2) . . ? F21 C32 C33 119.8(2) . . ? F21 C32 C31 119.3(2) . . ? C33 C32 C31 120.9(2) . . ? F22 C33 C32 121.3(2) . . ? F22 C33 C34 118.9(2) . . ? C32 C33 C34 119.7(2) . . ? F23 C34 C35 120.8(3) . . ? F23 C34 C33 119.3(2) . . ? C35 C34 C33 119.9(3) . . ? F24 C35 C36 120.1(2) . . ? F24 C35 C34 120.1(2) . . ? C36 C35 C34 119.8(3) . . ? F25 C36 C35 119.4(2) . . ? F25 C36 C31 119.7(2) . . ? C35 C36 C31 120.9(2) . . ? C38 C37 C42 119.4(3) . . ? C38 C37 O6 119.9(3) . . ? C42 C37 O6 120.3(2) . . ? F26 C38 C37 119.4(3) . . ? F26 C38 C39 119.8(3) . . ? C37 C38 C39 120.8(3) . . ? F27 C39 C38 120.2(3) . . ? F27 C39 C40 120.4(3) . . ? C38 C39 C40 119.4(3) . . ? F28 C40 C41 120.2(3) . . ? F28 C40 C39 119.1(3) . . ? C41 C40 C39 120.6(3) . . ? F29 C41 C40 120.5(3) . . ? F29 C41 C42 120.3(3) . . ? C40 C41 C42 119.2(3) . . ? F30 C42 C37 119.5(3) . . ? F30 C42 C41 120.0(3) . . ? C37 C42 C41 120.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N2 C1 N1 0.7(4) . . . . ? C2 N2 C1 O1 -179.6(2) . . . . ? C3 N1 C1 N2 -0.8(4) . . . . ? C3 N1 C1 O1 179.6(2) . . . . ? C4 O1 C1 N2 -174.9(2) . . . . ? C4 O1 C1 N1 4.8(4) . . . . ? C3 N3 C2 N2 -0.3(4) . . . . ? C3 N3 C2 O2 -179.5(2) . . . . ? C1 N2 C2 N3 -0.1(4) . . . . ? C1 N2 C2 O2 179.2(2) . . . . ? C10 O2 C2 N3 -176.2(2) . . . . ? C10 O2 C2 N2 4.5(3) . . . . ? C2 N3 C3 N1 0.1(4) . . . . ? C2 N3 C3 O3 -179.5(2) . . . . ? C1 N1 C3 N3 0.3(4) . . . . ? C1 N1 C3 O3 179.9(2) . . . . ? C16 O3 C3 N3 175.9(2) . . . . ? C16 O3 C3 N1 -3.7(3) . . . . ? C1 O1 C4 C5 82.6(3) . . . . ? C1 O1 C4 C9 -105.2(3) . . . . ? C9 C4 C5 F1 -178.2(3) . . . . ? O1 C4 C5 F1 -6.1(4) . . . . ? C9 C4 C5 C6 0.4(4) . . . . ? O1 C4 C5 C6 172.5(2) . . . . ? F1 C5 C6 F2 -1.1(5) . . . . ? C4 C5 C6 F2 -179.7(3) . . . . ? F1 C5 C6 C7 177.8(3) . . . . ? C4 C5 C6 C7 -0.8(5) . . . . ? F2 C6 C7 F3 0.2(5) . . . . ? C5 C6 C7 F3 -178.6(3) . . . . ? F2 C6 C7 C8 179.3(3) . . . . ? C5 C6 C7 C8 0.4(5) . . . . ? F3 C7 C8 F4 1.3(4) . . . . ? C6 C7 C8 F4 -177.8(3) . . . . ? F3 C7 C8 C9 179.4(3) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? C5 C4 C9 F5 179.5(3) . . . . ? O1 C4 C9 F5 7.4(4) . . . . ? C5 C4 C9 C8 0.3(4) . . . . ? O1 C4 C9 C8 -171.8(2) . . . . ? F4 C8 C9 F5 -1.9(4) . . . . ? C7 C8 C9 F5 -179.9(3) . . . . ? F4 C8 C9 C4 177.3(3) . . . . ? C7 C8 C9 C4 -0.7(4) . . . . ? C2 O2 C10 C15 -110.5(3) . . . . ? C2 O2 C10 C11 71.0(3) . . . . ? C15 C10 C11 F6 177.7(2) . . . . ? O2 C10 C11 F6 -3.8(4) . . . . ? C15 C10 C11 C12 0.5(4) . . . . ? O2 C10 C11 C12 178.9(2) . . . . ? F6 C11 C12 F7 1.0(4) . . . . ? C10 C11 C12 F7 178.3(2) . . . . ? F6 C11 C12 C13 -178.5(2) . . . . ? C10 C11 C12 C13 -1.2(4) . . . . ? F7 C12 C13 F8 0.7(4) . . . . ? C11 C12 C13 F8 -179.8(3) . . . . ? F7 C12 C13 C14 -177.6(3) . . . . ? C11 C12 C13 C14 1.9(4) . . . . ? F8 C13 C14 F9 -0.4(4) . . . . ? C12 C13 C14 F9 177.9(3) . . . . ? F8 C13 C14 C15 179.9(3) . . . . ? C12 C13 C14 C15 -1.9(4) . . . . ? C11 C10 C15 F10 -179.3(2) . . . . ? O2 C10 C15 F10 2.2(4) . . . . ? C11 C10 C15 C14 -0.4(4) . . . . ? O2 C10 C15 C14 -178.9(2) . . . . ? F9 C14 C15 F10 0.3(4) . . . . ? C13 C14 C15 F10 -180.0(3) . . . . ? F9 C14 C15 C10 -178.7(3) . . . . ? C13 C14 C15 C10 1.1(4) . . . . ? C3 O3 C16 C21 79.3(3) . . . . ? C3 O3 C16 C17 -104.7(3) . . . . ? C21 C16 C17 F11 179.5(2) . . . . ? O3 C16 C17 F11 3.4(4) . . . . ? C21 C16 C17 C18 -1.2(4) . . . . ? O3 C16 C17 C18 -177.3(2) . . . . ? F11 C17 C18 F12 -1.2(4) . . . . ? C16 C17 C18 F12 179.5(3) . . . . ? F11 C17 C18 C19 -179.4(3) . . . . ? C16 C17 C18 C19 1.2(4) . . . . ? F12 C18 C19 F13 -0.5(4) . . . . ? C17 C18 C19 F13 177.7(3) . . . . ? F12 C18 C19 C20 -178.9(3) . . . . ? C17 C18 C19 C20 -0.6(5) . . . . ? F13 C19 C20 F14 0.4(4) . . . . ? C18 C19 C20 F14 178.8(3) . . . . ? F13 C19 C20 C21 -178.4(3) . . . . ? C18 C19 C20 C21 0.0(5) . . . . ? C17 C16 C21 F15 -179.5(2) . . . . ? O3 C16 C21 F15 -3.5(4) . . . . ? C17 C16 C21 C20 0.6(4) . . . . ? O3 C16 C21 C20 176.5(2) . . . . ? F14 C20 C21 F15 1.3(4) . . . . ? C19 C20 C21 F15 -179.9(2) . . . . ? F14 C20 C21 C16 -178.7(2) . . . . ? C19 C20 C21 C16 0.0(4) . . . . ? C24 N4 C22 N5 -0.1(4) . . . . ? C24 N4 C22 O4 -180.0(2) . . . . ? C23 N5 C22 N4 -0.8(4) . . . . ? C23 N5 C22 O4 179.0(2) . . . . ? C25 O4 C22 N4 -2.9(3) . . . . ? C25 O4 C22 N5 177.2(2) . . . . ? C22 N5 C23 N6 0.6(4) . . . . ? C22 N5 C23 O5 179.5(2) . . . . ? C24 N6 C23 N5 0.5(4) . . . . ? C24 N6 C23 O5 -178.3(2) . . . . ? C31 O5 C23 N5 179.0(2) . . . . ? C31 O5 C23 N6 -2.0(3) . . . . ? C23 N6 C24 N4 -1.8(4) . . . . ? C23 N6 C24 O6 178.9(2) . . . . ? C22 N4 C24 N6 1.6(4) . . . . ? C22 N4 C24 O6 -179.0(2) . . . . ? C37 O6 C24 N6 -7.1(4) . . . . ? C37 O6 C24 N4 173.5(2) . . . . ? C22 O4 C25 C30 115.2(3) . . . . ? C22 O4 C25 C26 -69.7(3) . . . . ? C30 C25 C26 F16 -179.6(2) . . . . ? O4 C25 C26 F16 5.3(4) . . . . ? C30 C25 C26 C27 -1.1(4) . . . . ? O4 C25 C26 C27 -176.2(2) . . . . ? F16 C26 C27 F17 -0.3(4) . . . . ? C25 C26 C27 F17 -178.8(2) . . . . ? F16 C26 C27 C28 179.9(2) . . . . ? C25 C26 C27 C28 1.4(4) . . . . ? F17 C27 C28 F18 -1.0(4) . . . . ? C26 C27 C28 F18 178.7(2) . . . . ? F17 C27 C28 C29 179.6(2) . . . . ? C26 C27 C28 C29 -0.7(4) . . . . ? F18 C28 C29 F19 0.7(4) . . . . ? C27 C28 C29 F19 -179.9(3) . . . . ? F18 C28 C29 C30 -179.8(2) . . . . ? C27 C28 C29 C30 -0.4(4) . . . . ? C26 C25 C30 F20 180.0(2) . . . . ? O4 C25 C30 F20 -4.7(3) . . . . ? C26 C25 C30 C29 0.0(4) . . . . ? O4 C25 C30 C29 175.3(2) . . . . ? F19 C29 C30 F20 0.2(4) . . . . ? C28 C29 C30 F20 -179.2(2) . . . . ? F19 C29 C30 C25 -179.8(2) . . . . ? C28 C29 C30 C25 0.8(4) . . . . ? C23 O5 C31 C36 109.6(3) . . . . ? C23 O5 C31 C32 -76.7(3) . . . . ? C36 C31 C32 F21 179.6(2) . . . . ? O5 C31 C32 F21 5.9(4) . . . . ? C36 C31 C32 C33 0.0(4) . . . . ? O5 C31 C32 C33 -173.7(2) . . . . ? F21 C32 C33 F22 -2.0(4) . . . . ? C31 C32 C33 F22 177.6(2) . . . . ? F21 C32 C33 C34 179.1(2) . . . . ? C31 C32 C33 C34 -1.3(4) . . . . ? F22 C33 C34 F23 1.0(4) . . . . ? C32 C33 C34 F23 180.0(2) . . . . ? F22 C33 C34 C35 -177.9(2) . . . . ? C32 C33 C34 C35 1.1(4) . . . . ? F23 C34 C35 F24 1.4(4) . . . . ? C33 C34 C35 F24 -179.7(2) . . . . ? F23 C34 C35 C36 -178.4(2) . . . . ? C33 C34 C35 C36 0.5(4) . . . . ? F24 C35 C36 F25 -1.7(4) . . . . ? C34 C35 C36 F25 178.1(2) . . . . ? F24 C35 C36 C31 178.4(2) . . . . ? C34 C35 C36 C31 -1.8(4) . . . . ? O5 C31 C36 F25 -4.4(3) . . . . ? C32 C31 C36 F25 -178.4(2) . . . . ? O5 C31 C36 C35 175.5(2) . . . . ? C32 C31 C36 C35 1.5(4) . . . . ? C24 O6 C37 C38 101.4(3) . . . . ? C24 O6 C37 C42 -85.9(3) . . . . ? C42 C37 C38 F26 -179.0(2) . . . . ? O6 C37 C38 F26 -6.2(4) . . . . ? C42 C37 C38 C39 -0.8(4) . . . . ? O6 C37 C38 C39 172.0(2) . . . . ? F26 C38 C39 F27 0.6(4) . . . . ? C37 C38 C39 F27 -177.7(2) . . . . ? F26 C38 C39 C40 -179.4(3) . . . . ? C37 C38 C39 C40 2.4(4) . . . . ? F27 C39 C40 F28 -0.6(4) . . . . ? C38 C39 C40 F28 179.4(2) . . . . ? F27 C39 C40 C41 178.2(3) . . . . ? C38 C39 C40 C41 -1.9(4) . . . . ? F28 C40 C41 F29 0.0(4) . . . . ? C39 C40 C41 F29 -178.7(3) . . . . ? F28 C40 C41 C42 178.5(3) . . . . ? C39 C40 C41 C42 -0.2(4) . . . . ? C38 C37 C42 F30 177.4(2) . . . . ? O6 C37 C42 F30 4.6(4) . . . . ? C38 C37 C42 C41 -1.4(4) . . . . ? O6 C37 C42 C41 -174.1(2) . . . . ? F29 C41 C42 F30 1.6(4) . . . . ? C40 C41 C42 F30 -176.9(2) . . . . ? F29 C41 C42 C37 -179.7(2) . . . . ? C40 C41 C42 C37 1.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.92 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.234 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.053