# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_w1 _database_code_depnum_ccdc_archive 'CCDC 910217' #TrackingRef 'W1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C18 H12 F4 N2 O6' _chemical_formula_sum 'C18 H12 F4 N2 O6' _chemical_formula_weight 428.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2649(11) _cell_length_b 8.6837(17) _cell_length_c 10.192(2) _cell_angle_alpha 105.83(3) _cell_angle_beta 96.18(3) _cell_angle_gamma 101.40(3) _cell_volume 432.98(15) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 218 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 4235 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1955 _reflns_number_gt 1188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1371P)^2^+0.3238P] 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 1955 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.2420 _refine_ls_wR_factor_gt 0.1803 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 0.3485(4) 0.2059(2) 0.0468(2) 0.0424(5) Uani 1 1 d . . . O1 O 0.5420(5) 0.1593(3) -0.2957(2) 0.0426(6) Uani 1 1 d . . . F2 F 0.7807(5) 0.5306(3) -0.2027(2) 0.0532(7) Uani 1 1 d . . . C9 C 0.9593(5) -0.0855(3) -0.2770(3) 0.0274(6) Uani 1 1 d . . . H9 H 0.8980 -0.0092 -0.2128 0.080 Uiso 1 1 calc . . . O2 O 0.7923(5) 0.1474(3) -0.1089(2) 0.0503(7) Uani 1 1 d . . . O3 O 0.8372(6) -0.2880(4) -0.6430(2) 0.0563(8) Uani 1 1 d . . . H3 H 0.7210 -0.2406 -0.6557 0.080 Uiso 1 1 calc . . . C7 C 0.5694(6) 0.3607(4) -0.0819(3) 0.0304(7) Uani 1 1 d . . . C4 C 1.1422(6) -0.3037(4) -0.4643(3) 0.0389(8) Uani 1 1 d . . . H4 H 1.2101 -0.3765 -0.5281 0.080 Uiso 1 1 calc . . . C8 C 0.6412(6) 0.2092(4) -0.1711(3) 0.0327(7) Uani 1 1 d . . . C2 C 0.8539(6) -0.1250(4) -0.4107(3) 0.0346(7) Uani 1 1 d . . . H2A H 0.7229 -0.0764 -0.4375 0.080 Uiso 1 1 calc . . . C6 C 0.6427(6) 0.5131(4) -0.1022(3) 0.0341(7) Uani 1 1 d . . . C5 C 0.4261(6) 0.3512(4) 0.0218(3) 0.0331(7) Uani 1 1 d . . . C3 C 0.9403(6) -0.2382(4) -0.5091(3) 0.0363(7) Uani 1 1 d . . . C1 C 1.1480(7) -0.1500(4) -0.2312(3) 0.0406(8) Uani 1 1 d . . . H1 H 1.2148 -0.1203 -0.1372 0.080 Uiso 1 1 calc . . . N2 N 1.2410(6) -0.2606(5) -0.3254(3) 0.0530(9) Uani 1 1 d . . . H92 H 1.3622 -0.3035 -0.2975 0.080 Uiso 1 1 calc . . . 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 0.0574(12) 0.0307(10) 0.0430(11) 0.0123(8) 0.0138(9) 0.0150(8) O1 0.0543(13) 0.0453(15) 0.0263(11) -0.0005(10) 0.0028(10) 0.0258(11) F2 0.0756(15) 0.0458(13) 0.0462(12) 0.0129(9) 0.0376(11) 0.0197(10) C9 0.0363(14) 0.0221(13) 0.0242(13) 0.0023(10) 0.0101(11) 0.0118(11) O2 0.0701(17) 0.0556(17) 0.0338(12) 0.0072(11) 0.0073(12) 0.0438(14) O3 0.0656(16) 0.0699(19) 0.0314(12) -0.0008(12) -0.0016(12) 0.0399(15) C7 0.0370(14) 0.0297(15) 0.0246(13) 0.0027(11) 0.0027(11) 0.0173(12) C4 0.0428(17) 0.0385(18) 0.0370(16) 0.0051(13) 0.0109(14) 0.0202(14) C8 0.0378(15) 0.0338(16) 0.0292(14) 0.0060(12) 0.0084(12) 0.0182(12) C2 0.0375(15) 0.0325(16) 0.0348(15) 0.0064(13) 0.0071(12) 0.0152(12) C6 0.0435(16) 0.0358(17) 0.0241(13) 0.0052(12) 0.0120(12) 0.0141(13) C5 0.0441(16) 0.0297(16) 0.0277(14) 0.0075(12) 0.0052(12) 0.0156(12) C3 0.0412(16) 0.0381(17) 0.0292(14) 0.0054(13) 0.0054(13) 0.0154(13) C1 0.0480(18) 0.0433(19) 0.0323(15) 0.0103(14) 0.0067(14) 0.0166(15) N2 0.0523(17) 0.063(2) 0.0484(18) 0.0159(16) 0.0071(15) 0.0254(16) _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 1.348(4) . ? O1 C8 1.242(4) . ? F2 C6 1.342(3) . ? C9 C1 1.335(4) . ? C9 C2 1.338(4) . ? C9 H9 0.9300 . ? O2 C8 1.252(4) . ? O3 C3 1.330(4) . ? O3 H3 0.8200 . ? C7 C5 1.373(4) . ? C7 C6 1.381(4) . ? C7 C8 1.523(4) . ? C4 N2 1.375(5) . ? C4 C3 1.392(4) . ? C4 H4 0.9300 . ? C2 C3 1.384(4) . ? C2 H2A 0.9300 . ? C6 C5 1.378(4) 2_665 ? C5 C6 1.378(4) 2_665 ? C1 N2 1.366(4) . ? C1 H1 0.9300 . ? N2 H92 0.8600 . ? 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 C9 C2 123.3(3) . . ? C1 C9 H9 118.3 . . ? C2 C9 H9 118.3 . . ? C3 O3 H3 109.5 . . ? C5 C7 C6 117.1(3) . . ? C5 C7 C8 121.2(3) . . ? C6 C7 C8 121.7(3) . . ? N2 C4 C3 119.8(3) . . ? N2 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? O1 C8 O2 127.3(3) . . ? O1 C8 C7 117.1(3) . . ? O2 C8 C7 115.6(3) . . ? C9 C2 C3 119.8(3) . . ? C9 C2 H2A 120.1 . . ? C3 C2 H2A 120.1 . . ? F2 C6 C5 118.9(3) . 2_665 ? F2 C6 C7 120.1(3) . . ? C5 C6 C7 121.1(3) 2_665 . ? F1 C5 C7 119.9(3) . . ? F1 C5 C6 118.2(3) . 2_665 ? C7 C5 C6 121.9(3) . 2_665 ? O3 C3 C2 123.0(3) . . ? O3 C3 C4 119.1(3) . . ? C2 C3 C4 117.9(3) . . ? C9 C1 N2 118.6(3) . . ? C9 C1 H1 120.7 . . ? N2 C1 H1 120.7 . . ? C1 N2 C4 120.5(3) . . ? C1 N2 H92 119.7 . . ? C4 N2 H92 119.7 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.634 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.092 data_w2 _database_code_depnum_ccdc_archive 'CCDC 910218' #TrackingRef 'w2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C30 H24 F8 N4 O8' _chemical_formula_sum 'C30 H24 F8 N4 O8' _chemical_formula_weight 720.53 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.781(5) _cell_length_b 10.066(7) _cell_length_c 10.289(6) _cell_angle_alpha 99.273(10) _cell_angle_beta 107.452(9) _cell_angle_gamma 110.288(9) _cell_volume 777.2(8) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 4325 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.36 _reflns_number_total 3100 _reflns_number_gt 1821 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.3730P] 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 3100 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1581 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.3200(3) 0.6489(2) 0.37925(19) 0.0629(6) Uani 1 1 d . . . F2 F 0.5807(3) 0.5144(2) 0.77822(18) 0.0671(6) Uani 1 1 d . . . O4 O 0.2315(3) 0.6498(2) 0.6262(2) 0.0557(6) Uani 1 1 d . . . H4 H 0.2095 0.7034 0.6797 0.080 Uiso 1 1 calc . . . N1 N -0.0941(4) 0.5913(3) 0.2201(3) 0.0566(7) Uani 1 1 d . . . H1 H -0.0432 0.5327 0.2143 0.080 Uiso 1 1 calc . . . C8 C 0.4481(4) 0.5874(3) 0.5839(3) 0.0401(7) Uani 1 1 d . . . C13 C -0.2640(4) 0.7762(3) 0.2384(3) 0.0454(7) Uani 1 1 d . . . N2 N -0.3500(3) 0.8618(3) 0.2452(3) 0.0541(7) Uani 1 1 d . . . C12 C -0.1529(4) 0.7604(3) 0.3616(3) 0.0536(8) Uani 1 1 d . . . H12 H -0.1355 0.8132 0.4517 0.080 Uiso 1 1 calc . . . C7 C 0.5425(4) 0.5117(3) 0.6405(3) 0.0446(7) Uani 1 1 d . . . O3 O 0.5065(3) 0.7779(3) 0.7844(3) 0.0929(10) Uani 1 1 d . . . C6 C 0.3972(4) 0.6831(4) 0.6763(3) 0.0498(8) Uani 1 1 d . . . C15 C -0.1947(4) 0.6049(4) 0.1009(3) 0.0540(8) Uani 1 1 d . . . H15 H -0.2065 0.5519 0.0129 0.080 Uiso 1 1 calc . . . C5 C 0.4068(4) 0.5738(3) 0.4408(3) 0.0433(7) Uani 1 1 d . . . C14 C -0.2798(4) 0.6939(4) 0.1054(3) 0.0514(8) Uani 1 1 d . . . H14 H -0.3490 0.7012 0.0210 0.080 Uiso 1 1 calc . . . C10 C -0.3357(5) 0.9460(4) 0.3816(4) 0.0702(11) Uani 1 1 d . . . H10A H -0.4063 1.0007 0.3645 0.080 Uiso 1 1 calc . . . H10B H -0.2152 1.0135 0.4368 0.080 Uiso 1 1 calc . . . H10C H -0.3763 0.8789 0.4328 0.080 Uiso 1 1 calc . . . C11 C -0.0720(5) 0.6689(4) 0.3490(3) 0.0575(9) Uani 1 1 d . . . H11 H 0.0000 0.6596 0.4309 0.080 Uiso 1 1 calc . . . C9 C -0.4641(5) 0.8742(4) 0.1164(4) 0.0728(11) Uani 1 1 d . . . H9A H -0.5141 0.9404 0.1420 0.080 Uiso 1 1 calc . . . H9B H -0.5567 0.7781 0.0604 0.080 Uiso 1 1 calc . . . H9C H -0.3968 0.9121 0.0618 0.080 Uiso 1 1 calc . . . F3 F 0.1313(3) 0.0798(2) 0.28901(19) 0.0694(6) Uani 1 1 d . . . F4 F -0.1750(3) 0.1382(2) -0.1462(2) 0.0658(6) Uani 1 1 d . . . O1 O -0.1287(4) 0.1978(3) 0.2425(3) 0.0780(8) Uani 1 1 d . . . C2 C -0.0244(4) 0.1159(3) 0.0761(3) 0.0418(7) Uani 1 1 d . . . O2 O -0.0062(4) 0.3594(3) 0.1402(3) 0.0773(8) Uani 1 1 d . . . C3 C -0.0866(4) 0.0720(3) -0.0707(3) 0.0450(7) Uani 1 1 d . . . C4 C -0.0545(4) 0.2382(4) 0.1592(3) 0.0494(8) Uani 1 1 d . . . C1 C 0.0636(4) 0.0416(3) 0.1448(3) 0.0452(7) 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 0.0801(13) 0.0798(13) 0.0594(12) 0.0260(10) 0.0321(10) 0.0609(11) F2 0.0865(14) 0.0997(15) 0.0394(11) 0.0198(10) 0.0296(10) 0.0619(13) O4 0.0599(15) 0.0634(14) 0.0574(14) 0.0042(11) 0.0317(11) 0.0395(12) N1 0.0696(19) 0.0524(16) 0.0614(19) 0.0169(14) 0.0261(15) 0.0400(15) C8 0.0401(16) 0.0448(16) 0.0383(17) 0.0022(13) 0.0179(13) 0.0232(13) C13 0.0479(18) 0.0400(16) 0.0461(19) 0.0074(13) 0.0181(15) 0.0181(14) N2 0.0615(17) 0.0543(16) 0.0526(17) 0.0085(12) 0.0206(14) 0.0355(14) C12 0.069(2) 0.0496(18) 0.0421(18) 0.0069(14) 0.0175(16) 0.0305(17) C7 0.0492(18) 0.0568(18) 0.0344(16) 0.0079(13) 0.0194(14) 0.0289(15) O3 0.0754(18) 0.101(2) 0.0725(18) -0.0356(16) 0.0085(14) 0.0474(16) C6 0.056(2) 0.0567(19) 0.0452(19) 0.0033(15) 0.0217(16) 0.0362(17) C15 0.067(2) 0.057(2) 0.0464(19) 0.0121(15) 0.0241(17) 0.0351(18) C5 0.0458(17) 0.0493(17) 0.0449(18) 0.0112(13) 0.0188(14) 0.0313(15) C14 0.056(2) 0.0562(19) 0.0440(18) 0.0094(14) 0.0164(15) 0.0312(16) C10 0.093(3) 0.063(2) 0.067(2) 0.0083(18) 0.038(2) 0.045(2) C11 0.069(2) 0.054(2) 0.046(2) 0.0128(15) 0.0130(16) 0.0303(18) C9 0.069(2) 0.081(3) 0.073(3) 0.010(2) 0.0150(19) 0.052(2) F3 0.0958(15) 0.0876(14) 0.0423(11) 0.0118(10) 0.0271(10) 0.0610(13) F4 0.0859(14) 0.0765(13) 0.0649(13) 0.0257(10) 0.0319(11) 0.0630(12) O1 0.118(2) 0.0701(16) 0.103(2) 0.0321(15) 0.0875(19) 0.0617(16) C2 0.0484(17) 0.0386(15) 0.0526(19) 0.0096(13) 0.0303(15) 0.0265(14) O2 0.118(2) 0.0521(15) 0.102(2) 0.0243(14) 0.0742(18) 0.0529(15) C3 0.0553(19) 0.0510(17) 0.0489(19) 0.0175(14) 0.0259(15) 0.0387(16) C4 0.060(2) 0.0475(18) 0.057(2) 0.0086(15) 0.0311(17) 0.0359(16) C1 0.0566(19) 0.0504(17) 0.0392(17) 0.0093(14) 0.0245(15) 0.0309(15) _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 1.348(3) . ? F2 C7 1.348(3) . ? O4 C6 1.285(4) . ? O4 H4 0.8200 . ? N1 C15 1.337(4) . ? N1 C11 1.347(4) . ? N1 H1 0.8600 . ? C8 C5 1.378(4) . ? C8 C7 1.379(4) . ? C8 C6 1.513(4) . ? C13 N2 1.335(4) . ? C13 C12 1.419(4) . ? C13 C14 1.420(4) . ? N2 C9 1.455(4) . ? N2 C10 1.463(4) . ? C12 C11 1.356(4) . ? C12 H12 0.9300 . ? C7 C5 1.377(4) 2_666 ? O3 C6 1.205(4) . ? C15 C14 1.355(4) . ? C15 H15 0.9300 . ? C5 C7 1.377(4) 2_666 ? C14 H14 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? F3 C1 1.354(3) . ? F4 C3 1.346(3) . ? O1 C4 1.260(4) . ? C2 C1 1.378(4) . ? C2 C3 1.378(4) . ? C2 C4 1.529(4) . ? O2 C4 1.214(4) . ? C3 C1 1.379(4) 2 ? C1 C3 1.379(4) 2 ? 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 C6 O4 H4 109.5 . . ? C15 N1 C11 120.5(3) . . ? C15 N1 H1 119.8 . . ? C11 N1 H1 119.8 . . ? C5 C8 C7 116.5(2) . . ? C5 C8 C6 122.3(3) . . ? C7 C8 C6 121.1(3) . . ? N2 C13 C12 122.8(3) . . ? N2 C13 C14 121.4(3) . . ? C12 C13 C14 115.8(3) . . ? C13 N2 C9 121.2(3) . . ? C13 N2 C10 121.8(3) . . ? C9 N2 C10 117.0(3) . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? F2 C7 C5 117.9(3) . 2_666 ? F2 C7 C8 119.8(2) . . ? C5 C7 C8 122.2(3) 2_666 . ? O3 C6 O4 126.7(3) . . ? O3 C6 C8 120.7(3) . . ? O4 C6 C8 112.6(3) . . ? N1 C15 C14 121.6(3) . . ? N1 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? F1 C5 C7 118.9(3) . 2_666 ? F1 C5 C8 119.8(2) . . ? C7 C5 C8 121.3(3) 2_666 . ? C15 C14 C13 120.4(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 121.1(3) . . ? N1 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C2 C3 116.5(2) . . ? C1 C2 C4 121.5(3) . . ? C3 C2 C4 122.0(3) . . ? F4 C3 C2 120.4(2) . . ? F4 C3 C1 118.1(3) . 2 ? C2 C3 C1 121.5(3) . 2 ? O2 C4 O1 127.6(3) . . ? O2 C4 C2 119.0(3) . . ? O1 C4 C2 113.4(3) . . ? F3 C1 C2 120.1(2) . . ? F3 C1 C3 117.9(3) . 2 ? C2 C1 C3 121.9(3) . 2 ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.226 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.055 data_w3 _database_code_depnum_ccdc_archive 'CCDC 910219' #TrackingRef 'w3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C24 H14 F8 N6 O8' _chemical_formula_sum 'C24 H14 F8 N6 O8' _chemical_formula_weight 666.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0147(14) _cell_length_b 7.5439(15) _cell_length_c 12.600(3) _cell_angle_alpha 76.07(3) _cell_angle_beta 81.70(3) _cell_angle_gamma 88.92(3) _cell_volume 640.3(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 6093 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2853 _reflns_number_gt 2313 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1236P)^2^+0.1775P] 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 2853 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1904 _refine_ls_wR_factor_gt 0.1800 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 F4 F 0.2086(2) 0.6437(2) 0.11574(11) 0.0564(4) Uani 1 1 d . . . F3 F 0.5000(2) 0.4798(2) -0.21060(10) 0.0546(4) Uani 1 1 d . . . O4 O 0.0366(3) 0.7209(3) -0.06330(15) 0.0583(5) Uani 1 1 d . . . O3 O 0.1631(3) 0.6070(3) -0.20208(16) 0.0721(7) Uani 1 1 d . . . H3 H 0.0678 0.6515 -0.2285 0.080 Uiso 1 1 calc . . . C6 C 0.3351(3) 0.5677(3) -0.05273(15) 0.0335(4) Uani 1 1 d . . . C8 C 0.4934(3) 0.4923(3) -0.10648(16) 0.0357(4) Uani 1 1 d . . . C5 C 0.3495(3) 0.5732(3) 0.05564(16) 0.0360(4) Uani 1 1 d . . . C7 C 0.1623(3) 0.6414(3) -0.10637(16) 0.0364(4) Uani 1 1 d . . . F2 F 0.3787(2) 0.5452(3) 0.41798(14) 0.0681(5) Uani 1 1 d . . . O2 O 0.1252(3) 0.2387(3) 0.28662(15) 0.0612(6) Uani 1 1 d . . . O1 O 0.3193(3) 0.1575(2) 0.41291(13) 0.0563(5) Uani 1 1 d . . . N1 N 0.5361(3) -0.0140(3) 0.28045(14) 0.0425(4) Uani 1 1 d . . . N2 N 0.3532(3) 0.0559(3) 0.13767(15) 0.0435(4) Uani 1 1 d . . . H2A H 0.3577 0.0483 0.0679 0.080 Uiso 1 1 calc . . . H2B H 0.3434 0.1724 0.1408 0.080 Uiso 1 1 calc . . . H2C H 0.2514 -0.0072 0.1788 0.080 Uiso 1 1 calc . . . N3 N 0.6486(3) -0.0773(3) 0.10830(14) 0.0406(4) Uani 1 1 d . . . F1 F 0.2136(2) 0.7673(2) 0.53615(15) 0.0714(5) Uani 1 1 d . . . C9 C 0.5112(3) -0.0117(3) 0.17521(16) 0.0354(4) Uani 1 1 d . . . C2 C 0.1922(3) 0.5183(3) 0.45852(17) 0.0410(5) Uani 1 1 d . . . C4 C 0.1855(3) 0.2477(3) 0.37359(16) 0.0406(5) Uani 1 1 d . . . C3 C 0.0890(3) 0.3801(3) 0.43782(15) 0.0365(5) Uani 1 1 d . . . C11 C 0.8342(4) -0.1566(4) 0.2576(2) 0.0540(6) Uani 1 1 d . . . H11 H 0.9443 -0.2084 0.2846 0.080 Uiso 1 1 calc . . . C12 C 0.6942(4) -0.0865(3) 0.32171(18) 0.0515(6) Uani 1 1 d . . . H12 H 0.7081 -0.0888 0.3943 0.080 Uiso 1 1 calc . . . C10 C 0.8040(3) -0.1465(3) 0.14935(19) 0.0467(5) Uani 1 1 d . . . H10 H 0.8989 -0.1912 0.1035 0.080 Uiso 1 1 calc . . . C1 C 0.1049(3) 0.6351(3) 0.52023(17) 0.0411(5) 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 F4 0.0416(7) 0.0935(11) 0.0438(7) -0.0364(7) -0.0084(6) 0.0301(7) F3 0.0442(8) 0.0959(11) 0.0313(7) -0.0299(6) -0.0076(5) 0.0184(7) O4 0.0501(10) 0.0867(13) 0.0487(9) -0.0332(9) -0.0177(8) 0.0340(9) O3 0.0580(11) 0.1247(18) 0.0537(11) -0.0516(11) -0.0299(9) 0.0496(11) C6 0.0281(9) 0.0417(10) 0.0324(9) -0.0131(7) -0.0034(7) 0.0028(7) C8 0.0328(10) 0.0488(11) 0.0284(9) -0.0155(7) -0.0037(7) 0.0048(7) C5 0.0298(9) 0.0476(11) 0.0338(9) -0.0187(8) -0.0011(7) 0.0077(7) C7 0.0337(10) 0.0429(11) 0.0343(9) -0.0127(7) -0.0057(7) 0.0049(7) F2 0.0393(8) 0.1145(14) 0.0633(10) -0.0541(9) 0.0060(7) 0.0000(7) O2 0.0668(11) 0.0913(13) 0.0457(9) -0.0457(9) -0.0306(8) 0.0461(10) O1 0.0735(12) 0.0712(11) 0.0355(8) -0.0291(7) -0.0235(8) 0.0454(9) N1 0.0561(11) 0.0471(10) 0.0299(8) -0.0194(7) -0.0103(7) 0.0190(8) N2 0.0444(10) 0.0542(11) 0.0376(9) -0.0219(7) -0.0087(7) 0.0166(8) N3 0.0450(10) 0.0515(10) 0.0310(8) -0.0208(7) -0.0082(7) 0.0169(7) F1 0.0696(11) 0.0800(11) 0.0772(11) -0.0515(9) 0.0063(8) -0.0180(8) C9 0.0448(11) 0.0364(10) 0.0289(9) -0.0158(7) -0.0061(7) 0.0099(7) C2 0.0364(10) 0.0590(13) 0.0329(10) -0.0224(9) -0.0047(8) 0.0127(8) C4 0.0492(12) 0.0506(12) 0.0281(9) -0.0201(8) -0.0106(8) 0.0227(9) C3 0.0428(11) 0.0455(11) 0.0260(8) -0.0166(7) -0.0096(7) 0.0190(8) C11 0.0584(15) 0.0670(15) 0.0456(12) -0.0238(11) -0.0236(11) 0.0294(11) C12 0.0692(16) 0.0605(14) 0.0329(10) -0.0214(9) -0.0198(10) 0.0242(11) C10 0.0497(13) 0.0566(13) 0.0397(11) -0.0232(9) -0.0088(9) 0.0210(9) C1 0.0468(12) 0.0470(11) 0.0354(10) -0.0220(8) -0.0058(8) 0.0074(8) _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 F4 C5 1.338(2) . ? F3 C8 1.332(2) . ? O4 C7 1.196(3) . ? O3 C7 1.292(3) . ? O3 H3 0.8200 . ? C6 C5 1.394(3) . ? C6 C8 1.400(3) . ? C6 C7 1.505(3) . ? C8 C5 1.378(3) 2_665 ? C5 C8 1.378(3) 2_665 ? F2 C2 1.335(3) . ? O2 C4 1.247(2) . ? O1 C4 1.240(2) . ? N1 C12 1.344(3) . ? N1 C9 1.358(2) . ? N2 C9 1.314(3) . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? N3 C10 1.320(3) . ? N3 C9 1.354(3) . ? F1 C1 1.336(3) . ? C2 C3 1.375(3) . ? C2 C1 1.389(3) . ? C4 C3 1.522(2) . ? C3 C1 1.383(3) 2_566 ? C11 C12 1.362(3) . ? C11 C10 1.394(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C10 H10 0.9300 . ? C1 C3 1.383(3) 2_566 ? 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 C7 O3 H3 109.5 . . ? C5 C6 C8 114.87(18) . . ? C5 C6 C7 121.46(18) . . ? C8 C6 C7 123.66(18) . . ? F3 C8 C5 116.09(17) . 2_665 ? F3 C8 C6 121.41(18) . . ? C5 C8 C6 122.50(18) 2_665 . ? F4 C5 C8 116.58(17) . 2_665 ? F4 C5 C6 120.79(18) . . ? C8 C5 C6 122.63(18) 2_665 . ? O4 C7 O3 124.02(19) . . ? O4 C7 C6 122.93(18) . . ? O3 C7 C6 113.04(17) . . ? C12 N1 C9 120.96(18) . . ? C9 N2 H2A 109.5 . . ? C9 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C9 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C10 N3 C9 117.96(17) . . ? N2 C9 N3 119.67(17) . . ? N2 C9 N1 119.80(18) . . ? N3 C9 N1 120.53(19) . . ? F2 C2 C3 120.59(18) . . ? F2 C2 C1 118.3(2) . . ? C3 C2 C1 121.1(2) . . ? O1 C4 O2 125.45(17) . . ? O1 C4 C3 116.45(16) . . ? O2 C4 C3 118.10(17) . . ? C2 C3 C1 117.06(17) . 2_566 ? C2 C3 C4 121.29(19) . . ? C1 C3 C4 121.6(2) 2_566 . ? C12 C11 C10 116.5(2) . . ? C12 C11 H11 121.7 . . ? C10 C11 H11 121.7 . . ? N1 C12 C11 120.23(19) . . ? N1 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N3 C10 C11 123.7(2) . . ? N3 C10 H10 118.1 . . ? C11 C10 H10 118.1 . . ? F1 C1 C3 120.34(18) . 2_566 ? F1 C1 C2 117.8(2) . . ? C3 C1 C2 121.8(2) 2_566 . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.595 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.077 data_w4 _database_code_depnum_ccdc_archive 'CCDC 910220' #TrackingRef 'w4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C18 H10 F4 N2 O4' _chemical_formula_sum 'C18 H10 F4 N2 O4' _chemical_formula_weight 394.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.319(3) _cell_length_b 10.152(4) _cell_length_c 10.642(3) _cell_angle_alpha 87.500(6) _cell_angle_beta 73.992(4) _cell_angle_gamma 69.092(6) _cell_volume 805.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 5240 _diffrn_reflns_av_R_equivalents 0.0132 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.37 _reflns_number_total 3930 _reflns_number_gt 2785 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.1830P] 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 3930 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1436 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.18708(16) 0.68893(14) 0.97416(13) 0.0641(4) Uani 1 1 d . . . F2 F 0.42514(18) 0.53008(14) 0.76668(11) 0.0592(4) Uani 1 1 d . . . O2 O 0.2054(2) 0.81421(16) 1.20374(16) 0.0698(5) Uani 1 1 d . . . H2 H 0.1346 0.8632 1.2691 0.080 Uiso 1 1 calc . . . O3 O 0.1905(3) 0.63664(18) 1.32980(16) 0.0712(5) Uani 1 1 d . . . C18 C 0.3430(2) 0.5986(2) 0.98937(19) 0.0424(4) Uani 1 1 d . . . C17 C 0.3753(2) 0.58776(19) 1.11013(18) 0.0406(4) Uani 1 1 d . . . C16 C 0.4656(3) 0.5139(2) 0.88182(18) 0.0411(4) Uani 1 1 d . . . C15 C 0.2446(3) 0.6832(2) 1.2279(2) 0.0477(5) Uani 1 1 d . . . F3 F 0.15112(15) 0.08644(15) 0.00465(15) 0.0654(4) Uani 1 1 d . . . O1 O 0.1675(2) 0.35173(15) 0.10758(14) 0.0579(4) Uani 1 1 d . . . H1 H 0.0972 0.4175 0.1600 0.080 Uiso 1 1 calc . . . C14 C 0.3748(2) 0.11997(18) 0.08096(17) 0.0385(4) Uani 1 1 d . . . F4 F 0.61172(18) 0.13762(15) 0.14932(14) 0.0678(4) Uani 1 1 d . . . N2 N -0.9236(2) 1.02044(19) 0.63679(16) 0.0484(4) Uani 1 1 d . . . N1 N -0.1022(2) 0.54521(17) 0.25849(16) 0.0460(4) Uani 1 1 d . . . O4 O 0.2139(3) 0.24461(18) 0.28627(15) 0.0810(6) Uani 1 1 d . . . C4 C -0.6695(3) 0.9733(2) 0.45174(19) 0.0444(4) Uani 1 1 d . . . H4 H -0.6085 1.0060 0.3777 0.080 Uiso 1 1 calc . . . C1 C -0.5982(2) 0.83520(19) 0.48421(17) 0.0386(4) Uani 1 1 d . . . C2 C -0.4226(2) 0.73552(18) 0.40596(17) 0.0387(4) Uani 1 1 d . . . C13 C 0.2401(3) 0.24924(19) 0.16851(18) 0.0434(4) Uani 1 1 d . . . C12 C 0.5536(3) 0.0709(2) 0.07561(18) 0.0411(4) Uani 1 1 d . . . C10 C -0.3157(3) 0.6259(2) 0.46317(18) 0.0464(5) Uani 1 1 d . . . H10 H -0.3514 0.6160 0.5528 0.080 Uiso 1 1 calc . . . C11 C 0.3241(2) 0.0460(2) 0.00341(19) 0.0414(4) Uani 1 1 d . . . C7 C -0.3607(3) 0.7481(2) 0.27277(18) 0.0474(5) Uani 1 1 d . . . H7 H -0.4272 0.8216 0.2317 0.080 Uiso 1 1 calc . . . C9 C -0.1569(3) 0.5322(2) 0.3867(2) 0.0477(5) Uani 1 1 d . . . H9 H -0.0864 0.4585 0.4252 0.080 Uiso 1 1 calc . . . C5 C -0.8320(3) 1.0627(2) 0.5300(2) 0.0483(5) Uani 1 1 d . . . H5 H -0.8788 1.1553 0.5072 0.080 Uiso 1 1 calc . . . C6 C -0.6977(3) 0.7922(2) 0.5939(2) 0.0520(5) Uani 1 1 d . . . H6 H -0.6570 0.6993 0.6175 0.080 Uiso 1 1 calc . . . C8 C -0.1993(3) 0.6509(2) 0.20132(19) 0.0514(5) Uani 1 1 d . . . H8 H -0.1581 0.6594 0.1119 0.080 Uiso 1 1 calc . . . C3 C -0.8576(3) 0.8881(2) 0.6680(2) 0.0562(6) Uani 1 1 d . . . H3 H -0.9216 0.8585 0.7427 0.080 Uiso 1 1 calc . . . 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 0.0402(6) 0.0592(8) 0.0718(9) 0.0020(6) -0.0196(6) 0.0100(6) F2 0.0655(8) 0.0614(8) 0.0455(7) 0.0047(6) -0.0231(6) -0.0111(7) O2 0.0624(10) 0.0406(9) 0.0652(10) -0.0079(7) 0.0190(8) 0.0035(7) O3 0.0823(12) 0.0606(11) 0.0481(9) -0.0017(7) 0.0075(8) -0.0179(9) C18 0.0332(9) 0.0345(10) 0.0492(11) 0.0027(8) -0.0107(8) -0.0008(7) C17 0.0374(9) 0.0329(9) 0.0421(10) -0.0016(7) -0.0043(7) -0.0062(8) C16 0.0426(10) 0.0373(10) 0.0389(9) 0.0035(7) -0.0123(8) -0.0085(8) C15 0.0399(10) 0.0445(11) 0.0463(11) -0.0046(8) -0.0020(8) -0.0073(9) F3 0.0331(6) 0.0602(8) 0.0893(10) -0.0150(7) -0.0162(6) 0.0007(6) O1 0.0560(9) 0.0408(8) 0.0448(8) -0.0065(6) -0.0037(6) 0.0133(7) C14 0.0370(9) 0.0295(9) 0.0344(9) 0.0001(6) -0.0007(7) -0.0016(7) F4 0.0606(8) 0.0609(9) 0.0804(10) -0.0235(7) -0.0258(7) -0.0122(7) N2 0.0394(8) 0.0438(9) 0.0469(9) -0.0104(7) -0.0057(7) -0.0006(7) N1 0.0401(8) 0.0382(9) 0.0462(9) -0.0076(7) -0.0054(7) -0.0022(7) O4 0.1031(14) 0.0532(10) 0.0382(8) -0.0020(7) -0.0001(8) 0.0145(10) C4 0.0428(10) 0.0350(10) 0.0413(10) -0.0004(7) -0.0046(8) -0.0025(8) C1 0.0370(9) 0.0344(9) 0.0341(9) -0.0049(7) -0.0074(7) -0.0016(7) C2 0.0367(9) 0.0311(9) 0.0368(9) -0.0045(7) -0.0052(7) -0.0017(7) C13 0.0419(10) 0.0330(10) 0.0381(10) -0.0036(7) 0.0003(7) -0.0014(8) C12 0.0406(9) 0.0343(9) 0.0421(10) -0.0035(7) -0.0096(7) -0.0068(8) C10 0.0454(10) 0.0418(11) 0.0369(10) -0.0022(7) -0.0081(8) 0.0001(8) C11 0.0306(8) 0.0363(10) 0.0459(10) -0.0005(7) -0.0057(7) -0.0019(7) C7 0.0467(11) 0.0381(10) 0.0389(10) 0.0013(7) -0.0038(8) 0.0004(8) C9 0.0422(10) 0.0403(11) 0.0465(11) -0.0025(8) -0.0130(8) 0.0026(8) C5 0.0445(11) 0.0336(10) 0.0517(11) -0.0063(8) -0.0097(9) 0.0019(8) C6 0.0473(11) 0.0401(11) 0.0473(11) 0.0047(8) -0.0011(9) -0.0001(9) C8 0.0487(11) 0.0441(11) 0.0406(10) -0.0028(8) 0.0019(8) -0.0026(9) C3 0.0458(11) 0.0556(13) 0.0462(11) -0.0003(9) 0.0039(9) -0.0058(10) _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 C18 1.343(2) . ? F2 C16 1.346(2) . ? O2 C15 1.284(3) . ? O2 H2 0.8200 . ? O3 C15 1.200(3) . ? C18 C17 1.376(3) . ? C18 C16 1.380(3) . ? C17 C16 1.380(3) 2_667 ? C17 C15 1.515(3) . ? C16 C17 1.380(3) 2_667 ? F3 C11 1.345(2) . ? O1 C13 1.256(2) . ? O1 H1 0.8200 . ? C14 C12 1.375(3) . ? C14 C11 1.377(3) . ? C14 C13 1.525(2) . ? F4 C12 1.341(2) . ? N2 C3 1.324(3) . ? N2 C5 1.330(3) . ? N1 C8 1.330(3) . ? N1 C9 1.331(3) . ? O4 C13 1.213(2) . ? C4 C5 1.383(3) . ? C4 C1 1.384(3) . ? C4 H4 0.9300 . ? C1 C6 1.385(3) . ? C1 C2 1.483(2) . ? C2 C7 1.385(3) . ? C2 C10 1.390(3) . ? C12 C11 1.379(3) 2_655 ? C10 C9 1.375(3) . ? C10 H10 0.9300 . ? C11 C12 1.379(3) 2_655 ? C7 C8 1.383(3) . ? C7 H7 0.9300 . ? C9 H9 0.9300 . ? C5 H5 0.9300 . ? C6 C3 1.379(3) . ? C6 H6 0.9300 . ? C8 H8 0.9300 . ? C3 H3 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 C15 O2 H2 109.5 . . ? F1 C18 C17 120.49(17) . . ? F1 C18 C16 117.98(17) . . ? C17 C18 C16 121.48(17) . . ? C18 C17 C16 116.43(16) . 2_667 ? C18 C17 C15 122.00(17) . . ? C16 C17 C15 121.57(18) 2_667 . ? F2 C16 C18 118.30(17) . . ? F2 C16 C17 119.60(17) . 2_667 ? C18 C16 C17 122.08(17) . 2_667 ? O3 C15 O2 126.54(19) . . ? O3 C15 C17 121.8(2) . . ? O2 C15 C17 111.68(17) . . ? C13 O1 H1 109.5 . . ? C12 C14 C11 116.39(16) . . ? C12 C14 C13 121.68(18) . . ? C11 C14 C13 121.92(17) . . ? C3 N2 C5 118.74(16) . . ? C8 N1 C9 120.57(16) . . ? C5 C4 C1 119.66(18) . . ? C5 C4 H4 120.2 . . ? C1 C4 H4 120.2 . . ? C4 C1 C6 117.33(16) . . ? C4 C1 C2 122.12(16) . . ? C6 C1 C2 120.54(17) . . ? C7 C2 C10 117.86(16) . . ? C7 C2 C1 120.82(16) . . ? C10 C2 C1 121.32(16) . . ? O4 C13 O1 126.80(17) . . ? O4 C13 C14 118.86(17) . . ? O1 C13 C14 114.34(16) . . ? F4 C12 C14 119.44(17) . . ? F4 C12 C11 118.67(18) . 2_655 ? C14 C12 C11 121.88(18) . 2_655 ? C9 C10 C2 119.73(17) . . ? C9 C10 H10 120.1 . . ? C2 C10 H10 120.1 . . ? F3 C11 C14 119.86(16) . . ? F3 C11 C12 118.41(18) . 2_655 ? C14 C11 C12 121.72(17) . 2_655 ? C8 C7 C2 119.61(18) . . ? C8 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? N1 C9 C10 121.17(18) . . ? N1 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? N2 C5 C4 122.12(18) . . ? N2 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C3 C6 C1 119.58(19) . . ? C3 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? N1 C8 C7 121.03(18) . . ? N1 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? N2 C3 C6 122.52(19) . . ? N2 C3 H3 118.7 . . ? C6 C3 H3 118.7 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.382 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.055 data_w5 _database_code_depnum_ccdc_archive 'CCDC 910221' #TrackingRef 'w5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C20 H10 F4 N4 O5' _chemical_formula_sum 'C20 H10 F4 N4 O5' _chemical_formula_weight 462.32 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.041(2) _cell_length_b 6.8049(14) _cell_length_c 13.405(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.97(3) _cell_angle_gamma 90.00 _cell_volume 899.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 8591 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2057 _reflns_number_gt 1866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.3777P] 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 2057 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.49311(7) 0.14442(11) 0.08970(6) 0.0215(2) Uani 1 1 d . . . O1 O 1.5000 0.86972(18) 0.2500 0.0147(3) Uani 1 2 d S . . F2 F 0.73764(7) 0.67130(11) -0.01874(6) 0.0210(2) Uani 1 1 d . . . O2 O 0.76028(9) 0.11646(13) 0.05670(7) 0.0190(2) Uani 1 1 d . . . H2 H 0.8344 0.0699 0.0819 0.080 Uiso 1 1 calc . . . N1 N 0.99761(10) 0.97015(16) 0.12609(8) 0.0164(2) Uani 1 1 d . . . O3 O 0.84857(9) 0.39302(14) 0.13287(8) 0.0233(2) Uani 1 1 d . . . C9 C 1.23303(12) 1.02702(19) 0.19265(9) 0.0164(3) Uani 1 1 d . . . H9 H 1.3033 1.1155 0.2138 0.080 Uiso 1 1 calc . . . C10 C 1.39314(12) 0.74445(19) 0.22685(9) 0.0144(3) Uani 1 1 d . . . C8 C 1.25694(12) 0.82534(18) 0.19488(9) 0.0142(3) Uani 1 1 d . . . C6 C 1.02062(13) 0.77587(19) 0.12961(10) 0.0189(3) Uani 1 1 d . . . H6 H 0.9483 0.6908 0.1082 0.080 Uiso 1 1 calc . . . C2 C 0.62385(12) 0.40045(18) 0.03775(9) 0.0141(3) Uani 1 1 d . . . N2 N 1.42917(10) 0.56151(16) 0.23472(8) 0.0174(2) Uani 1 1 d . . . C4 C 0.49917(13) 0.31722(18) 0.04325(9) 0.0152(3) Uani 1 1 d . . . C3 C 0.62136(12) 0.58535(18) -0.00636(9) 0.0149(3) Uani 1 1 d . . . C7 C 1.10176(13) 1.09230(18) 0.15806(10) 0.0176(3) Uani 1 1 d . . . H7 H 1.0851 1.2268 0.1570 0.080 Uiso 1 1 calc . . . C5 C 1.14815(13) 0.69781(19) 0.16402(10) 0.0186(3) Uani 1 1 d . . . H5 H 1.1612 0.5625 0.1665 0.080 Uiso 1 1 calc . . . C1 C 0.75722(12) 0.30053(18) 0.08090(9) 0.0153(3) 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 0.0174(4) 0.0150(4) 0.0313(4) 0.0106(3) 0.0029(3) 0.0003(3) O1 0.0104(5) 0.0132(6) 0.0193(6) 0.000 -0.0001(5) 0.000 F2 0.0118(4) 0.0186(4) 0.0318(4) 0.0079(3) 0.0021(3) -0.0029(3) O2 0.0147(4) 0.0145(5) 0.0254(5) -0.0008(3) -0.0023(4) 0.0025(3) N1 0.0136(5) 0.0155(5) 0.0193(5) 0.0016(4) 0.0013(4) -0.0002(4) O3 0.0164(4) 0.0161(5) 0.0330(5) 0.0002(4) -0.0068(4) -0.0008(3) C9 0.0134(6) 0.0156(6) 0.0200(6) -0.0005(5) 0.0023(4) -0.0022(4) C10 0.0121(5) 0.0156(6) 0.0149(5) -0.0004(4) 0.0013(4) -0.0021(4) C8 0.0116(5) 0.0166(6) 0.0140(5) 0.0010(4) 0.0013(4) 0.0000(4) C6 0.0144(6) 0.0161(6) 0.0245(6) 0.0006(5) -0.0006(5) -0.0024(5) C2 0.0130(5) 0.0134(6) 0.0149(6) 0.0000(4) 0.0000(4) 0.0009(4) N2 0.0121(5) 0.0162(5) 0.0225(5) 0.0003(4) -0.0002(4) 0.0004(4) C4 0.0168(6) 0.0110(6) 0.0169(6) 0.0029(4) 0.0007(4) 0.0002(4) C3 0.0113(5) 0.0150(6) 0.0179(6) 0.0009(4) 0.0019(4) -0.0024(4) C7 0.0156(6) 0.0138(6) 0.0231(6) 0.0007(5) 0.0027(5) -0.0002(4) C5 0.0160(6) 0.0133(6) 0.0247(6) 0.0005(5) -0.0001(5) -0.0012(5) C1 0.0128(5) 0.0150(6) 0.0175(6) 0.0034(4) 0.0017(4) 0.0007(4) _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 C4 1.3373(14) . ? O1 C10 1.3592(14) . ? O1 C10 1.3592(14) 2_855 ? F2 C3 1.3441(14) . ? O2 C1 1.2957(16) . ? O2 H2 0.8200 . ? N1 C7 1.3408(16) . ? N1 C6 1.3414(17) . ? O3 C1 1.2163(16) . ? C9 C7 1.3847(17) . ? C9 C8 1.3925(18) . ? C9 H9 0.9300 . ? C10 N2 1.2951(17) . ? C10 C8 1.4609(16) . ? C8 C5 1.3949(17) . ? C6 C5 1.3820(18) . ? C6 H6 0.9300 . ? C2 C3 1.3884(17) . ? C2 C4 1.3888(17) . ? C2 C1 1.5151(16) . ? N2 N2 1.403(2) 2_855 ? C4 C3 1.3860(17) 3_665 ? C3 C4 1.3860(17) 3_665 ? C7 H7 0.9300 . ? C5 H5 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 C10 O1 C10 102.32(13) . 2_855 ? C1 O2 H2 109.5 . . ? C7 N1 C6 118.76(11) . . ? C7 C9 C8 118.20(11) . . ? C7 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? N2 C10 O1 112.84(10) . . ? N2 C10 C8 128.13(11) . . ? O1 C10 C8 119.01(11) . . ? C9 C8 C5 118.99(11) . . ? C9 C8 C10 121.71(11) . . ? C5 C8 C10 119.29(11) . . ? N1 C6 C5 122.22(11) . . ? N1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C3 C2 C4 116.66(11) . . ? C3 C2 C1 120.81(11) . . ? C4 C2 C1 122.48(11) . . ? C10 N2 N2 106.00(7) . 2_855 ? F1 C4 C3 118.21(11) . 3_665 ? F1 C4 C2 120.30(11) . . ? C3 C4 C2 121.38(11) 3_665 . ? F2 C3 C4 117.89(11) . 3_665 ? F2 C3 C2 120.08(11) . . ? C4 C3 C2 121.95(11) 3_665 . ? N1 C7 C9 122.89(12) . . ? N1 C7 H7 118.6 . . ? C9 C7 H7 118.6 . . ? C6 C5 C8 118.91(12) . . ? C6 C5 H5 120.5 . . ? C8 C5 H5 120.5 . . ? O3 C1 O2 126.33(11) . . ? O3 C1 C2 120.12(11) . . ? O2 C1 C2 113.55(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.382 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.068 data_w12 _database_code_depnum_ccdc_archive 'CCDC 910222' #TrackingRef 'w6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C40 H20 F8 N4 O8' _chemical_formula_sum 'C40 H20 F8 N4 O8' _chemical_formula_weight 836.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9033(16) _cell_length_b 7.9444(16) _cell_length_c 13.749(3) _cell_angle_alpha 99.65(3) _cell_angle_beta 96.63(3) _cell_angle_gamma 91.26(3) _cell_volume 844.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 7937 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3682 _reflns_number_gt 2916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1431P)^2^+0.9696P] 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 3682 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.2335 _refine_ls_wR_factor_gt 0.2249 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.2332(2) 0.7785(2) 0.42327(14) 0.0405(5) Uani 1 1 d . . . F2 F 0.1737(2) 1.0976(2) 0.49765(14) 0.0401(5) Uani 1 1 d . . . O3 O 0.5122(3) 1.3954(3) 0.67265(15) 0.0406(5) Uani 1 1 d . . . H3 H 0.4897 1.4932 0.6957 0.080 Uiso 1 1 calc . . . C20 C 0.3362(3) 1.0531(4) 0.49818(19) 0.0284(6) Uani 1 1 d . . . C19 C 0.3679(3) 0.8863(3) 0.45959(19) 0.0288(6) Uani 1 1 d . . . C18 C 0.4679(3) 1.1715(3) 0.53968(18) 0.0278(6) Uani 1 1 d . . . O4 O 0.3336(3) 1.4363(3) 0.54096(18) 0.0518(7) Uani 1 1 d . . . C17 C 0.4301(4) 1.3518(3) 0.5849(2) 0.0305(6) Uani 1 1 d . . . F3 F 0.1784(2) 0.8808(2) 0.92813(13) 0.0399(5) Uani 1 1 d . . . F4 F 0.7743(2) 0.8319(2) 0.93995(13) 0.0392(5) Uani 1 1 d . . . O1 O 0.5122(3) 0.6863(3) 0.77257(15) 0.0356(5) Uani 1 1 d . . . O2 O 0.3680(4) 0.5665(3) 0.8745(2) 0.0674(9) Uani 1 1 d . . . C16 C 0.4748(3) 0.8494(3) 0.92833(18) 0.0269(6) Uani 1 1 d . . . C15 C 0.6361(3) 0.9136(3) 0.96833(19) 0.0269(6) Uani 1 1 d . . . C14 C 0.3385(3) 0.9377(3) 0.96215(18) 0.0268(5) Uani 1 1 d . . . C13 C 0.4476(4) 0.6843(3) 0.8530(2) 0.0324(6) Uani 1 1 d . . . C9 C 0.1048(4) 0.9027(4) 0.7058(2) 0.0320(6) Uani 1 1 d . . . N1 N -0.2694(3) 1.1051(3) 0.80442(19) 0.0351(6) Uani 1 1 d . . . C8 C -0.0591(3) 0.9282(3) 0.73450(19) 0.0277(6) Uani 1 1 d . . . N2 N -0.1740(3) 0.7927(3) 0.71687(17) 0.0320(5) Uani 1 1 d . . . H2 H -0.2730 0.8077 0.7362 0.080 Uiso 1 1 calc . . . C3 C -0.1065(4) 1.0902(4) 0.78347(19) 0.0299(6) Uani 1 1 d . . . C11 C 0.0186(4) 0.6095(4) 0.6392(2) 0.0415(7) Uani 1 1 d . . . H11 H 0.0422 0.5021 0.6063 0.080 Uiso 1 1 calc . . . C10 C 0.1397(4) 0.7403(4) 0.6566(2) 0.0389(7) Uani 1 1 d . . . H10 H 0.2464 0.7211 0.6356 0.080 Uiso 1 1 calc . . . C7 C 0.2279(4) 1.0438(4) 0.7301(2) 0.0405(7) Uani 1 1 d . . . H7 H 0.3374 1.0296 0.7124 0.080 Uiso 1 1 calc . . . C2 C 0.0195(4) 1.2239(4) 0.8067(2) 0.0350(6) Uani 1 1 d . . . C4 C -0.1915(5) 1.3946(4) 0.8819(3) 0.0483(8) Uani 1 1 d . . . H4 H -0.2252 1.4962 0.9171 0.080 Uiso 1 1 calc . . . C6 C 0.1865(4) 1.1964(4) 0.7783(2) 0.0418(7) Uani 1 1 d . . . H6 H 0.2683 1.2858 0.7934 0.080 Uiso 1 1 calc . . . C12 C -0.1396(4) 0.6390(4) 0.6713(2) 0.0378(7) Uani 1 1 d . . . H12 H -0.2221 0.5505 0.6608 0.080 Uiso 1 1 calc . . . C1 C -0.3078(4) 1.2549(4) 0.8524(2) 0.0411(7) Uani 1 1 d . . . H1 H -0.4189 1.2685 0.8675 0.080 Uiso 1 1 calc . . . C5 C -0.0284(5) 1.3808(4) 0.8588(3) 0.0454(8) Uani 1 1 d . . . H5 H 0.0498 1.4731 0.8770 0.080 Uiso 1 1 calc . . . 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 0.0325(10) 0.0311(9) 0.0500(10) -0.0106(7) -0.0011(7) -0.0067(7) F2 0.0276(9) 0.0384(10) 0.0496(11) -0.0054(8) 0.0034(7) 0.0066(7) O3 0.0552(14) 0.0261(11) 0.0331(11) -0.0124(8) -0.0014(9) 0.0045(9) C20 0.0260(13) 0.0297(14) 0.0265(12) -0.0036(10) 0.0022(9) 0.0035(10) C19 0.0288(14) 0.0263(13) 0.0266(12) -0.0059(9) -0.0002(9) -0.0043(10) C18 0.0343(15) 0.0220(13) 0.0238(12) -0.0052(9) 0.0030(9) 0.0029(10) O4 0.0625(16) 0.0369(13) 0.0488(14) -0.0073(10) -0.0065(11) 0.0212(12) C17 0.0343(14) 0.0239(13) 0.0305(13) -0.0058(10) 0.0069(10) 0.0014(11) F3 0.0287(9) 0.0432(11) 0.0412(10) -0.0077(7) 0.0001(7) -0.0091(7) F4 0.0337(10) 0.0341(10) 0.0461(10) -0.0083(7) 0.0099(7) 0.0086(7) O1 0.0414(12) 0.0277(10) 0.0324(10) -0.0130(7) 0.0090(8) -0.0033(8) O2 0.092(2) 0.0340(13) 0.0719(18) -0.0202(12) 0.0421(16) -0.0292(14) C16 0.0345(15) 0.0196(12) 0.0242(11) -0.0038(9) 0.0056(10) -0.0025(10) C15 0.0305(14) 0.0213(13) 0.0274(12) -0.0027(9) 0.0072(9) 0.0025(10) C14 0.0285(13) 0.0246(13) 0.0244(11) -0.0025(9) 0.0015(9) -0.0047(10) C13 0.0355(15) 0.0199(13) 0.0368(14) -0.0105(10) 0.0066(11) -0.0031(10) C9 0.0311(15) 0.0357(15) 0.0290(13) 0.0053(11) 0.0041(10) -0.0013(11) N1 0.0344(13) 0.0319(13) 0.0403(13) 0.0073(10) 0.0075(10) 0.0035(10) C8 0.0272(14) 0.0286(14) 0.0267(12) 0.0042(10) 0.0018(9) -0.0026(10) N2 0.0310(13) 0.0299(13) 0.0337(12) 0.0000(9) 0.0058(9) -0.0020(9) C3 0.0350(15) 0.0265(14) 0.0284(13) 0.0066(10) 0.0028(10) -0.0004(11) C11 0.0466(19) 0.0335(16) 0.0416(16) -0.0041(12) 0.0078(13) 0.0062(13) C10 0.0346(16) 0.0479(18) 0.0337(14) 0.0027(12) 0.0070(11) 0.0055(13) C7 0.0325(16) 0.0491(19) 0.0405(16) 0.0089(13) 0.0070(12) -0.0061(13) C2 0.0398(17) 0.0284(15) 0.0359(15) 0.0065(11) 0.0002(11) -0.0057(12) C4 0.065(2) 0.0295(16) 0.0487(18) 0.0016(13) 0.0045(16) 0.0126(15) C6 0.0368(17) 0.0407(17) 0.0462(17) 0.0068(13) 0.0022(13) -0.0134(13) C12 0.0433(17) 0.0268(15) 0.0404(16) -0.0021(11) 0.0045(12) -0.0019(12) C1 0.0448(18) 0.0345(17) 0.0461(17) 0.0091(13) 0.0090(13) 0.0109(13) C5 0.056(2) 0.0270(15) 0.0493(18) 0.0025(13) -0.0011(15) -0.0056(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 C19 1.345(3) . ? F2 C20 1.339(3) . ? O3 C17 1.290(3) . ? O3 H3 0.8200 . ? C20 C19 1.382(4) . ? C20 C18 1.390(4) . ? C19 C18 1.386(4) 2_676 ? C18 C19 1.386(4) 2_676 ? C18 C17 1.513(3) . ? O4 C17 1.205(4) . ? F3 C14 1.338(3) . ? F4 C15 1.346(3) . ? O1 C13 1.272(4) . ? O2 C13 1.212(4) . ? C16 C15 1.380(4) . ? C16 C14 1.381(4) . ? C16 C13 1.523(3) . ? C15 C14 1.384(3) 2_677 ? C14 C15 1.384(3) 2_677 ? C9 C10 1.401(4) . ? C9 C8 1.406(4) . ? C9 C7 1.438(4) . ? N1 C1 1.320(4) . ? N1 C3 1.355(4) . ? C8 N2 1.364(4) . ? C8 C3 1.427(4) . ? N2 C12 1.325(4) . ? N2 H2 0.8600 . ? C3 C2 1.410(4) . ? C11 C10 1.368(5) . ? C11 C12 1.385(5) . ? C11 H11 0.9300 . ? C10 H10 0.9300 . ? C7 C6 1.347(5) . ? C7 H7 0.9300 . ? C2 C5 1.412(4) . ? C2 C6 1.430(5) . ? C4 C5 1.365(6) . ? C4 C1 1.399(5) . ? C4 H4 0.9300 . ? C6 H6 0.9300 . ? C12 H12 0.9300 . ? C1 H1 0.9300 . ? C5 H5 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 C17 O3 H3 109.5 . . ? F2 C20 C19 118.2(2) . . ? F2 C20 C18 120.2(2) . . ? C19 C20 C18 121.6(2) . . ? F1 C19 C20 117.9(2) . . ? F1 C19 C18 120.3(2) . 2_676 ? C20 C19 C18 121.8(2) . 2_676 ? C19 C18 C20 116.6(2) 2_676 . ? C19 C18 C17 122.6(2) 2_676 . ? C20 C18 C17 120.7(2) . . ? O4 C17 O3 127.4(3) . . ? O4 C17 C18 121.4(2) . . ? O3 C17 C18 111.1(2) . . ? C15 C16 C14 117.2(2) . . ? C15 C16 C13 121.5(2) . . ? C14 C16 C13 121.2(2) . . ? F4 C15 C16 120.2(2) . . ? F4 C15 C14 118.1(2) . 2_677 ? C16 C15 C14 121.7(2) . 2_677 ? F3 C14 C16 120.5(2) . . ? F3 C14 C15 118.5(2) . 2_677 ? C16 C14 C15 121.1(2) . 2_677 ? O2 C13 O1 126.8(2) . . ? O2 C13 C16 118.1(3) . . ? O1 C13 C16 115.1(2) . . ? C10 C9 C8 118.1(3) . . ? C10 C9 C7 123.8(3) . . ? C8 C9 C7 118.1(3) . . ? C1 N1 C3 116.3(3) . . ? N2 C8 C9 118.6(2) . . ? N2 C8 C3 119.5(2) . . ? C9 C8 C3 121.9(3) . . ? C12 N2 C8 122.9(3) . . ? C12 N2 H2 118.6 . . ? C8 N2 H2 118.6 . . ? N1 C3 C2 124.4(3) . . ? N1 C3 C8 117.9(2) . . ? C2 C3 C8 117.7(3) . . ? C10 C11 C12 119.2(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C11 C10 C9 120.8(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C6 C7 C9 120.8(3) . . ? C6 C7 H7 119.6 . . ? C9 C7 H7 119.6 . . ? C3 C2 C5 116.7(3) . . ? C3 C2 C6 120.0(3) . . ? C5 C2 C6 123.3(3) . . ? C5 C4 C1 119.6(3) . . ? C5 C4 H4 120.2 . . ? C1 C4 H4 120.2 . . ? C7 C6 C2 121.4(3) . . ? C7 C6 H6 119.3 . . ? C2 C6 H6 119.3 . . ? N2 C12 C11 120.4(3) . . ? N2 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? N1 C1 C4 124.0(3) . . ? N1 C1 H1 118.0 . . ? C4 C1 H1 118.0 . . ? C4 C5 C2 118.9(3) . . ? C4 C5 H5 120.6 . . ? C2 C5 H5 120.6 . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.404 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.115 data_w134 _database_code_depnum_ccdc_archive 'CCDC 910223' #TrackingRef 'w7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C20 H12 F4 N2 O5' _chemical_formula_sum 'C20 H12 F4 N2 O5' _chemical_formula_weight 436.32 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8627(16) _cell_length_b 9.6759(19) _cell_length_c 13.503(3) _cell_angle_alpha 79.34(3) _cell_angle_beta 81.08(3) _cell_angle_gamma 66.64(3) _cell_volume 923.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 8923 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4101 _reflns_number_gt 2897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1234P)^2^+0.1010P] 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 4101 _refine_ls_number_parameters 288 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1883 _refine_ls_wR_factor_gt 0.1461 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.18788(17) 0.40080(12) 0.01381(9) 0.0458(3) Uani 1 1 d . . . F2 F -0.09694(19) 0.33354(13) 0.34555(9) 0.0529(4) Uani 1 1 d . . . F3 F 0.2527(2) 0.11906(13) -0.00396(10) 0.0554(4) Uani 1 1 d . . . F4 F -0.0293(2) 0.05057(14) 0.32642(11) 0.0613(4) Uani 1 1 d . . . O1 O -0.1666(2) 0.61470(15) 0.23116(13) 0.0497(4) Uani 1 1 d . . . O3 O 0.3105(2) -0.16848(15) 0.11963(15) 0.0561(5) Uani 1 1 d . . . O2 O 0.1041(2) 0.60307(14) 0.14606(15) 0.0569(5) Uani 1 1 d . . . H2 H 0.0669 0.6926 0.1543 0.080 Uiso 1 1 calc . . . C16 C -0.0128(3) 0.28504(18) 0.25734(14) 0.0335(4) Uani 1 1 d . . . C18 C 0.1314(2) 0.31812(17) 0.09335(14) 0.0308(4) Uani 1 1 d . . . C17 C 0.0387(2) 0.38073(17) 0.17957(14) 0.0301(4) Uani 1 1 d . . . C19 C 0.1658(3) 0.16922(19) 0.08356(14) 0.0340(4) Uani 1 1 d . . . O4 O 0.0132(2) -0.12668(16) 0.16575(17) 0.0649(6) Uani 1 1 d . . . C14 C 0.1108(2) 0.07496(18) 0.15986(15) 0.0333(4) Uani 1 1 d . . . C13 C -0.0154(2) 0.54787(18) 0.18814(14) 0.0332(4) Uani 1 1 d . . . C20 C 0.1519(3) -0.08907(19) 0.14713(17) 0.0394(4) Uani 1 1 d . . . C15 C 0.0232(3) 0.13579(19) 0.24709(15) 0.0371(4) Uani 1 1 d . . . N1 N 0.5317(2) 0.18218(18) 0.21593(13) 0.0400(4) Uani 1 1 d . . . C4 C 0.3126(3) 0.3708(2) 0.44111(17) 0.0474(5) Uani 1 1 d . . . C5 C 0.3731(3) 0.2595(2) 0.37624(15) 0.0387(4) Uani 1 1 d . . . N2 N 0.3462(3) 0.1273(2) 0.39888(15) 0.0492(5) Uani 1 1 d . . . H5 H 0.3840 0.0618 0.3571 0.080 Uiso 1 1 calc . . . C8 C 0.4672(2) 0.2889(2) 0.27981(15) 0.0354(4) Uani 1 1 d . . . C9 C 0.4924(3) 0.4271(2) 0.24913(15) 0.0396(4) Uani 1 1 d . . . C11 C 0.6361(3) 0.3416(2) 0.08884(17) 0.0471(5) Uani 1 1 d . . . H11A H 0.6906 0.3581 0.0239 0.057 Uiso 1 1 calc R . . C10 C 0.5759(3) 0.4521(2) 0.15213(17) 0.0444(5) Uani 1 1 d . . . H10A H 0.5911 0.5437 0.1299 0.053 Uiso 1 1 calc R . . C7 C 0.4273(3) 0.5373(2) 0.31824(19) 0.0523(6) Uani 1 1 d . . . H7A H 0.4442 0.6288 0.2996 0.063 Uiso 1 1 calc R . . C12 C 0.6134(3) 0.2060(2) 0.12415(16) 0.0435(5) Uani 1 1 d . . . H12A H 0.6563 0.1298 0.0829 0.052 Uiso 1 1 calc R . . C1 C 0.2594(4) 0.1036(3) 0.4878(2) 0.0583(6) Uani 1 1 d . . . H1A H 0.2386 0.0136 0.5042 0.070 Uiso 1 1 calc R . . C2 C 0.1963(4) 0.2047(3) 0.5592(2) 0.0667(7) Uani 1 1 d . . . H2A H 0.1381 0.1811 0.6217 0.080 Uiso 1 1 calc R . . C3 C 0.2219(4) 0.3385(3) 0.5356(2) 0.0640(7) Uani 1 1 d . . . H3A H 0.1797 0.4082 0.5816 0.077 Uiso 1 1 calc R . . C6 C 0.3422(4) 0.5098(3) 0.40946(19) 0.0579(6) Uani 1 1 d . . . H6A H 0.3015 0.5828 0.4532 0.069 Uiso 1 1 calc R . . O1W O 0.5503(3) 0.90092(18) 0.21738(16) 0.0609(5) Uani 1 1 d D . . H1WA H 0.654(3) 0.832(4) 0.216(3) 0.130(16) Uiso 1 1 d D . . H1WB H 0.487(4) 0.883(4) 0.182(2) 0.091(12) Uiso 1 1 d 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 0.0617(7) 0.0305(6) 0.0456(7) -0.0044(5) 0.0107(5) -0.0238(5) F2 0.0838(9) 0.0363(6) 0.0347(7) -0.0126(5) 0.0127(6) -0.0221(6) F3 0.0827(9) 0.0364(6) 0.0464(8) -0.0209(5) 0.0182(6) -0.0240(6) F4 0.0976(10) 0.0371(6) 0.0509(8) -0.0012(5) 0.0145(7) -0.0371(7) O1 0.0574(8) 0.0262(6) 0.0597(10) -0.0154(6) 0.0114(7) -0.0116(6) O3 0.0529(9) 0.0285(7) 0.0887(13) -0.0229(7) 0.0038(8) -0.0145(7) O2 0.0519(8) 0.0263(7) 0.0994(14) -0.0246(7) 0.0111(8) -0.0216(7) C16 0.0452(9) 0.0255(8) 0.0322(9) -0.0093(7) 0.0020(7) -0.0154(8) C18 0.0384(8) 0.0213(7) 0.0354(9) -0.0046(6) 0.0020(7) -0.0156(7) C17 0.0366(8) 0.0204(7) 0.0368(10) -0.0078(6) -0.0038(7) -0.0126(7) C19 0.0425(9) 0.0250(8) 0.0368(10) -0.0126(7) 0.0028(7) -0.0138(7) O4 0.0556(9) 0.0294(7) 0.1185(17) -0.0257(8) 0.0028(9) -0.0226(7) C14 0.0421(9) 0.0204(8) 0.0417(10) -0.0076(7) -0.0031(7) -0.0151(7) C13 0.0436(9) 0.0204(7) 0.0383(10) -0.0081(6) -0.0025(7) -0.0138(7) C20 0.0499(10) 0.0202(8) 0.0527(12) -0.0104(7) -0.0040(8) -0.0159(8) C15 0.0520(10) 0.0237(8) 0.0382(10) -0.0018(7) 0.0007(8) -0.0199(8) N1 0.0404(8) 0.0374(8) 0.0424(9) -0.0122(7) -0.0008(7) -0.0132(7) C4 0.0593(12) 0.0471(11) 0.0395(11) -0.0128(9) 0.0034(9) -0.0240(10) C5 0.0435(9) 0.0378(10) 0.0352(10) -0.0058(7) -0.0023(7) -0.0161(8) N2 0.0632(11) 0.0420(9) 0.0460(11) -0.0084(7) 0.0037(8) -0.0256(9) C8 0.0370(9) 0.0340(9) 0.0365(10) -0.0085(7) -0.0026(7) -0.0135(8) C9 0.0436(9) 0.0348(9) 0.0405(11) -0.0059(8) -0.0016(8) -0.0156(8) C11 0.0463(10) 0.0505(12) 0.0425(12) -0.0073(9) 0.0023(8) -0.0180(10) C10 0.0479(11) 0.0393(10) 0.0467(12) -0.0045(8) 0.0003(9) -0.0195(9) C7 0.0687(14) 0.0414(11) 0.0512(13) -0.0163(9) 0.0050(10) -0.0249(11) C12 0.0459(10) 0.0449(11) 0.0382(11) -0.0139(8) 0.0047(8) -0.0150(9) C1 0.0730(15) 0.0545(13) 0.0503(14) -0.0011(10) 0.0053(11) -0.0338(12) C2 0.0853(17) 0.0735(17) 0.0432(14) -0.0063(12) 0.0121(12) -0.0391(15) C3 0.0869(17) 0.0673(15) 0.0399(13) -0.0179(11) 0.0116(12) -0.0332(14) C6 0.0810(16) 0.0501(12) 0.0498(14) -0.0228(10) 0.0062(11) -0.0300(12) O1W 0.0566(10) 0.0397(8) 0.0860(14) -0.0246(8) -0.0060(9) -0.0110(8) _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 C18 1.344(2) . ? F2 C16 1.339(2) . ? F3 C19 1.341(2) . ? F4 C15 1.343(2) . ? O1 C13 1.218(2) . ? O3 C20 1.219(2) . ? O2 C13 1.270(2) . ? O2 H2 0.8200 . ? C16 C15 1.387(2) . ? C16 C17 1.389(3) . ? C18 C17 1.379(2) . ? C18 C19 1.384(2) . ? C17 C13 1.523(2) . ? C19 C14 1.381(3) . ? O4 C20 1.257(3) . ? C14 C15 1.375(3) . ? C14 C20 1.526(2) . ? N1 C12 1.330(3) . ? N1 C8 1.359(2) . ? C4 C5 1.403(3) . ? C4 C3 1.407(3) . ? C4 C6 1.432(3) . ? C5 N2 1.350(3) . ? C5 C8 1.433(3) . ? N2 C1 1.315(3) . ? N2 H5 0.8600 . ? C8 C9 1.407(3) . ? C9 C10 1.395(3) . ? C9 C7 1.434(3) . ? C11 C12 1.381(3) . ? C11 C10 1.382(3) . ? C11 H11A 0.9300 . ? C10 H10A 0.9300 . ? C7 C6 1.342(3) . ? C7 H7A 0.9300 . ? C12 H12A 0.9300 . ? C1 C2 1.396(4) . ? C1 H1A 0.9300 . ? C2 C3 1.361(4) . ? C2 H2A 0.9300 . ? C3 H3A 0.9300 . ? C6 H6A 0.9300 . ? O1W H1WA 0.821(18) . ? O1W H1WB 0.824(17) . ? 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 C13 O2 H2 109.5 . . ? F2 C16 C15 117.66(16) . . ? F2 C16 C17 120.95(14) . . ? C15 C16 C17 121.39(17) . . ? F1 C18 C17 121.21(14) . . ? F1 C18 C19 117.03(16) . . ? C17 C18 C19 121.73(16) . . ? C18 C17 C16 116.47(14) . . ? C18 C17 C13 122.45(16) . . ? C16 C17 C13 121.00(16) . . ? F3 C19 C14 120.48(15) . . ? F3 C19 C18 117.63(17) . . ? C14 C19 C18 121.88(17) . . ? C15 C14 C19 116.49(15) . . ? C15 C14 C20 122.81(17) . . ? C19 C14 C20 120.68(17) . . ? O1 C13 O2 127.15(15) . . ? O1 C13 C17 118.16(16) . . ? O2 C13 C17 114.66(15) . . ? O3 C20 O4 126.93(16) . . ? O3 C20 C14 118.40(17) . . ? O4 C20 C14 114.66(16) . . ? F4 C15 C14 120.47(15) . . ? F4 C15 C16 117.52(17) . . ? C14 C15 C16 122.01(17) . . ? C12 N1 C8 121.98(17) . . ? C5 C4 C3 116.7(2) . . ? C5 C4 C6 120.0(2) . . ? C3 C4 C6 123.3(2) . . ? N2 C5 C4 123.88(19) . . ? N2 C5 C8 118.23(18) . . ? C4 C5 C8 117.89(19) . . ? C1 N2 C5 116.8(2) . . ? C1 N2 H5 121.6 . . ? C5 N2 H5 121.6 . . ? N1 C8 C9 119.07(18) . . ? N1 C8 C5 119.55(18) . . ? C9 C8 C5 121.37(18) . . ? C10 C9 C8 118.55(18) . . ? C10 C9 C7 123.00(19) . . ? C8 C9 C7 118.43(19) . . ? C12 C11 C10 118.6(2) . . ? C12 C11 H11A 120.7 . . ? C10 C11 H11A 120.7 . . ? C11 C10 C9 120.42(19) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C6 C7 C9 120.7(2) . . ? C6 C7 H7A 119.7 . . ? C9 C7 H7A 119.7 . . ? N1 C12 C11 121.37(19) . . ? N1 C12 H12A 119.3 . . ? C11 C12 H12A 119.3 . . ? N2 C1 C2 124.3(2) . . ? N2 C1 H1A 117.8 . . ? C2 C1 H1A 117.8 . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C7 C6 C4 121.5(2) . . ? C7 C6 H6A 119.2 . . ? C4 C6 H6A 119.2 . . ? H1WA O1W H1WB 107(3) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.536 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.088 data_w8 _database_code_depnum_ccdc_archive 'CCDC 910224' #TrackingRef 'w8.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C11 H6 F4 N2 O4' _chemical_formula_sum 'C11 H6 F4 N2 O4' _chemical_formula_weight 306.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 9.7141(19) _cell_length_b 7.2300(14) _cell_length_c 17.407(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1222.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10863 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2756 _reflns_number_gt 2643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.0441P] 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 0.4(4) _refine_ls_number_reflns 2756 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 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 0.63366(9) 0.40827(15) 0.39209(5) 0.0451(2) Uani 1 1 d . . . F2 F 0.36961(8) 0.35193(15) 0.42045(5) 0.0439(2) Uani 1 1 d . . . F3 F 0.42763(10) 0.59197(15) 0.67112(5) 0.0434(2) Uani 1 1 d . . . F4 F 0.69145(9) 0.64959(14) 0.64211(5) 0.0448(2) Uani 1 1 d . . . O4 O 0.90273(10) 0.48495(16) 0.55049(6) 0.0396(2) Uani 1 1 d . . . H4 H 0.9834 0.5036 0.5389 0.080 Uiso 1 1 calc . . . O3 O 0.15461(10) 0.50867(16) 0.51184(6) 0.0363(2) Uani 1 1 d . . . O2 O 0.20125(11) 0.36450(16) 0.62154(6) 0.0390(2) Uani 1 1 d . . . O1 O 0.85983(11) 0.64121(18) 0.44258(7) 0.0442(3) Uani 1 1 d . . . C11 C 0.23544(12) 0.44431(17) 0.56183(7) 0.0267(2) Uani 1 1 d . . . C10 C 0.82264(13) 0.55909(17) 0.49892(8) 0.0288(3) Uani 1 1 d . . . C6 C 0.47559(13) 0.54487(17) 0.60162(7) 0.0280(3) Uani 1 1 d . . . C5 C 0.38834(12) 0.47246(17) 0.54626(7) 0.0260(2) Uani 1 1 d . . . C4 C 0.44649(14) 0.42875(18) 0.47592(8) 0.0285(3) Uani 1 1 d . . . C3 C 0.58440(13) 0.45741(18) 0.46126(8) 0.0293(3) Uani 1 1 d . . . C2 C 0.61419(14) 0.57327(17) 0.58700(8) 0.0289(3) Uani 1 1 d . . . C1 C 0.67194(13) 0.53030(18) 0.51627(7) 0.0278(3) Uani 1 1 d . . . N2 N 0.14277(16) 0.5889(2) 0.35057(8) 0.0491(3) Uani 1 1 d . . . H2 H 0.1560 0.5788 0.3992 0.080 Uiso 1 1 calc . . . N1 N 0.16287(15) 0.6766(2) 0.23474(8) 0.0444(3) Uani 1 1 d . . . H1 H 0.1917 0.7335 0.1944 0.080 Uiso 1 1 calc . . . C9 C 0.0589(2) 0.5502(3) 0.23666(10) 0.0520(4) Uani 1 1 d . . . H9 H 0.0065 0.5102 0.1952 0.080 Uiso 1 1 calc . . . C8 C 0.04660(19) 0.4949(3) 0.30929(11) 0.0506(4) Uani 1 1 d . . . H8 H -0.0157 0.4085 0.3282 0.080 Uiso 1 1 calc . . . C7 C 0.21174(19) 0.6971(3) 0.30434(10) 0.0501(4) Uani 1 1 d . . . H7 H 0.2833 0.7754 0.3185 0.080 Uiso 1 1 calc . . . 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 0.0284(4) 0.0712(6) 0.0356(5) -0.0145(4) 0.0067(3) -0.0021(4) F2 0.0263(4) 0.0671(6) 0.0384(5) -0.0159(4) -0.0053(3) -0.0058(4) F3 0.0302(4) 0.0699(6) 0.0301(4) -0.0120(4) 0.0044(3) -0.0018(4) F4 0.0266(4) 0.0692(6) 0.0387(5) -0.0140(4) -0.0071(3) -0.0076(4) O4 0.0168(4) 0.0596(6) 0.0425(6) 0.0141(5) 0.0003(4) -0.0002(4) O3 0.0177(4) 0.0588(6) 0.0326(5) 0.0124(4) -0.0013(3) -0.0002(4) O2 0.0272(4) 0.0562(6) 0.0337(5) 0.0147(4) 0.0018(4) -0.0001(4) O1 0.0286(5) 0.0646(7) 0.0394(6) 0.0142(5) 0.0039(4) -0.0025(5) C11 0.0170(5) 0.0329(5) 0.0301(6) 0.0007(4) 0.0003(5) 0.0002(4) C10 0.0199(6) 0.0358(6) 0.0308(6) -0.0006(5) 0.0012(5) -0.0017(5) C6 0.0223(6) 0.0362(6) 0.0255(6) -0.0003(4) 0.0014(5) 0.0033(5) C5 0.0178(5) 0.0303(5) 0.0297(6) 0.0027(4) -0.0016(5) 0.0014(4) C4 0.0202(6) 0.0369(6) 0.0285(6) -0.0028(4) -0.0035(4) -0.0019(5) C3 0.0213(6) 0.0371(6) 0.0295(6) -0.0017(5) 0.0007(5) 0.0025(5) C2 0.0214(5) 0.0345(6) 0.0308(6) -0.0023(4) -0.0042(5) 0.0001(5) C1 0.0177(5) 0.0328(6) 0.0329(7) 0.0022(5) 0.0009(5) 0.0006(4) N2 0.0466(8) 0.0737(9) 0.0270(6) 0.0075(6) 0.0011(5) 0.0090(7) N1 0.0480(7) 0.0546(7) 0.0305(6) 0.0090(5) 0.0084(5) 0.0033(6) C9 0.0459(9) 0.0744(12) 0.0356(8) -0.0064(8) -0.0009(7) -0.0043(8) C8 0.0492(9) 0.0582(9) 0.0445(9) 0.0070(8) 0.0113(8) -0.0034(8) C7 0.0463(8) 0.0649(10) 0.0391(8) -0.0026(7) -0.0005(7) -0.0041(8) _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 C3 1.3434(16) . ? F2 C4 1.3411(15) . ? F3 C6 1.3404(14) . ? F4 C2 1.3372(15) . ? O4 C10 1.3033(16) . ? O4 H4 0.8200 . ? O3 C11 1.2611(15) . ? O2 C11 1.2342(17) . ? O1 C10 1.2021(17) . ? C11 C5 1.5235(16) . ? C10 C1 1.5091(17) . ? C6 C2 1.3855(18) . ? C6 C5 1.3860(18) . ? C5 C4 1.3849(19) . ? C4 C3 1.3794(18) . ? C3 C1 1.3850(19) . ? C2 C1 1.3882(19) . ? N2 C7 1.307(2) . ? N2 C8 1.361(3) . ? N2 H2 0.8600 . ? N1 C7 1.310(2) . ? N1 C9 1.362(3) . ? N1 H1 0.8600 . ? C9 C8 1.331(3) . ? C9 H9 0.9300 . ? C8 H8 0.9300 . ? C7 H7 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 C10 O4 H4 109.5 . . ? O2 C11 O3 125.88(12) . . ? O2 C11 C5 118.33(11) . . ? O3 C11 C5 115.78(11) . . ? O1 C10 O4 125.85(12) . . ? O1 C10 C1 121.53(12) . . ? O4 C10 C1 112.61(11) . . ? F3 C6 C2 117.77(11) . . ? F3 C6 C5 120.72(11) . . ? C2 C6 C5 121.50(11) . . ? C4 C5 C6 116.84(11) . . ? C4 C5 C11 121.63(12) . . ? C6 C5 C11 121.53(12) . . ? F2 C4 C3 118.02(12) . . ? F2 C4 C5 120.26(11) . . ? C3 C4 C5 121.70(12) . . ? F1 C3 C4 118.17(12) . . ? F1 C3 C1 120.10(11) . . ? C4 C3 C1 121.70(13) . . ? F4 C2 C6 118.35(12) . . ? F4 C2 C1 120.12(11) . . ? C6 C2 C1 121.50(11) . . ? C3 C1 C2 116.76(11) . . ? C3 C1 C10 120.65(12) . . ? C2 C1 C10 122.59(12) . . ? C7 N2 C8 109.02(14) . . ? C7 N2 H2 125.5 . . ? C8 N2 H2 125.5 . . ? C7 N1 C9 108.79(15) . . ? C7 N1 H1 125.6 . . ? C9 N1 H1 125.6 . . ? C8 C9 N1 106.93(16) . . ? C8 C9 H9 126.5 . . ? N1 C9 H9 126.5 . . ? C9 C8 N2 106.85(15) . . ? C9 C8 H8 126.6 . . ? N2 C8 H8 126.6 . . ? N2 C7 N1 108.40(17) . . ? N2 C7 H7 125.8 . . ? N1 C7 H7 125.8 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.290 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.052