# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 182/1868 data_k00272a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H48 F12 N4 O10' _chemical_formula_weight 1213.02 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 Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 18.4480(2) _cell_length_b 28.7380(4) _cell_length_c 9.6088(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5094.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 7636 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.49 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2496 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9473 _exptl_absorpt_correction_T_max 0.9537 _exptl_absorpt_process_details 'Denzo-SMN, Otwinowski & Minor 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans & \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7636 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1553 _reflns_number_gt 1326 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'Bruker SHELXTL V5.1' _computing_structure_refinement 'Bruker SHELXTL V5.1' _computing_molecular_graphics 'Bruker SHELXTL V5.1' _computing_publication_material 'Bruker SHELXTL V5.1' _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^)+(0.0453P)^2^+1.4823P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0018(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details ? _refine_ls_number_reflns 1553 _refine_ls_number_parameters 196 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.035 _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 0.02745(8) 0.59508(5) 0.21227(17) 0.0476(4) Uani 1 1 d . . . F2 F 0.12265(8) 0.55293(5) 0.20668(16) 0.0466(4) Uani 1 1 d . . . F3 F 0.10371(9) 0.59795(5) 0.38232(17) 0.0460(4) Uani 1 1 d . . . O1 O 0.21408(9) 0.50698(6) 0.7061(2) 0.0481(5) Uani 1 1 d . . . O2 O 0.08156(10) 0.37305(5) 0.7143(2) 0.0417(4) Uani 1 1 d . . . O3 O 0.0000 0.5000 0.2710(2) 0.0284(5) Uani 1 2 d S . . N1 N 0.15121(11) 0.43895(7) 0.7426(2) 0.0371(5) Uani 1 1 d . . . C1 C 0.03187(12) 0.53139(7) 0.3706(2) 0.0238(4) Uani 1 1 d . . . C2 C 0.07973(10) 0.49944(7) 0.4625(2) 0.0239(4) Uani 1 1 d . . . H2A H 0.0851 0.5123 0.5586 0.029 Uiso 1 1 calc R . . C3 C 0.15363(12) 0.48299(8) 0.4038(3) 0.0326(5) Uani 1 1 d . . . H3A H 0.1844 0.5084 0.3641 0.039 Uiso 1 1 calc R . . C4 C 0.19159(13) 0.45297(8) 0.5149(3) 0.0403(6) Uani 1 1 d . . . H4A H 0.2427 0.4462 0.4865 0.048 Uiso 1 1 calc R . . C5 C 0.18946(12) 0.47081(9) 0.6618(3) 0.0381(6) Uani 1 1 d . . . C6 C 0.12132(12) 0.40252(8) 0.6659(3) 0.0360(6) Uani 1 1 d . . . C7 C 0.14648(12) 0.40781(8) 0.5167(3) 0.0372(6) Uani 1 1 d . . . H7A H 0.1774 0.3807 0.4894 0.045 Uiso 1 1 calc R . . C8 C 0.08756(12) 0.41651(8) 0.4048(3) 0.0333(5) Uani 1 1 d . . . H8A H 0.0646 0.3877 0.3664 0.040 Uiso 1 1 calc R . . C9 C 0.03319(11) 0.45317(7) 0.4627(2) 0.0232(4) Uani 1 1 d . . . H9 H 0.0170 0.4449 0.5589 0.028 Uiso 1 1 calc R . . C10 C 0.13256(15) 0.44473(9) 0.2990(3) 0.0417(6) Uani 1 1 d . . . H10A H 0.1750 0.4273 0.2633 0.050 Uiso 1 1 calc R . . H10B H 0.1031 0.4567 0.2207 0.050 Uiso 1 1 calc R . . C11 C 0.07122(13) 0.56914(8) 0.2911(3) 0.0334(5) Uani 1 1 d . . . C12 C 0.13389(15) 0.44696(9) 0.8897(3) 0.0429(6) Uani 1 1 d . . . H12A H 0.1740 0.4641 0.9348 0.052 Uiso 1 1 calc R . . H12B H 0.1282 0.4167 0.9379 0.052 Uiso 1 1 calc R . . C13 C 0.06451(13) 0.47472(8) 0.9015(3) 0.0333(5) Uani 1 1 d . . . C14 C -0.00197(15) 0.45204(8) 0.9041(3) 0.0354(5) Uani 1 1 d . . . H14A H -0.0034 0.4190 0.9062 0.043 Uiso 1 1 calc R . . C15 C -0.06606(14) 0.47687(8) 0.9035(3) 0.0370(6) Uani 1 1 d . . . H15 H -0.1112 0.4609 0.9044 0.044 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 0.0651(10) 0.0401(8) 0.0377(8) 0.0180(7) -0.0024(8) -0.0102(7) F2 0.0560(9) 0.0503(8) 0.0336(8) 0.0048(7) 0.0171(8) -0.0153(7) F3 0.0640(9) 0.0374(8) 0.0367(8) -0.0019(7) 0.0004(7) -0.0279(7) O1 0.0356(9) 0.0454(10) 0.0632(12) 0.0036(10) -0.0209(10) -0.0090(8) O2 0.0452(9) 0.0255(8) 0.0545(11) 0.0063(9) -0.0004(9) 0.0023(7) O3 0.0427(12) 0.0264(10) 0.0160(10) 0.000 0.000 -0.0131(10) N1 0.0312(10) 0.0309(10) 0.0493(15) 0.0037(9) -0.0113(9) 0.0042(9) C1 0.0312(10) 0.0224(10) 0.0179(11) -0.0006(8) 0.0001(8) -0.0088(9) C2 0.0233(9) 0.0247(10) 0.0237(10) -0.0026(9) 0.0039(9) -0.0008(8) C3 0.0266(10) 0.0315(11) 0.0397(13) -0.0043(10) 0.0111(10) -0.0024(9) C4 0.0220(10) 0.0354(13) 0.0634(18) -0.0031(12) 0.0067(11) 0.0050(10) C5 0.0192(9) 0.0379(12) 0.0571(17) 0.0054(12) -0.0109(11) 0.0037(10) C6 0.0298(11) 0.0236(11) 0.0546(16) 0.0009(11) -0.0058(11) 0.0093(9) C7 0.0284(11) 0.0271(11) 0.0561(16) -0.0027(11) 0.0058(11) 0.0072(10) C8 0.0331(11) 0.0265(11) 0.0404(13) -0.0084(10) 0.0098(11) 0.0012(10) C9 0.0246(9) 0.0209(9) 0.0240(10) -0.0008(9) 0.0045(9) -0.0010(8) C10 0.0422(13) 0.0379(14) 0.0448(16) -0.0120(11) 0.0204(12) -0.0026(12) C11 0.0436(13) 0.0310(12) 0.0255(11) 0.0006(10) 0.0015(10) -0.0131(11) C12 0.0476(14) 0.0387(14) 0.0425(15) 0.0080(12) -0.0193(12) 0.0023(11) C13 0.0428(12) 0.0328(12) 0.0242(11) 0.0043(10) -0.0098(10) -0.0027(10) C14 0.0507(14) 0.0259(10) 0.0297(12) 0.0022(10) -0.0018(11) -0.0095(11) C15 0.0443(13) 0.0335(12) 0.0331(13) -0.0036(11) 0.0091(11) -0.0101(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 C11 1.335(3) . ? F2 C11 1.332(3) . ? F3 C11 1.346(3) . ? O1 C5 1.212(3) . ? O2 C6 1.213(3) . ? O3 C1 1.440(3) . ? O3 C1 1.440(3) 2_565 ? N1 C5 1.393(4) . ? N1 C6 1.394(3) . ? N1 C12 1.467(4) . ? C1 C11 1.512(3) . ? C1 C2 1.550(3) . ? C1 C9 1.556(3) 2_565 ? C2 C3 1.549(3) . ? C2 C9 1.583(3) . ? C3 C10 1.540(4) . ? C3 C4 1.541(4) . ? C4 C5 1.502(4) . ? C4 C7 1.542(3) . ? C6 C7 1.515(4) . ? C7 C8 1.549(4) . ? C8 C10 1.543(4) . ? C8 C9 1.558(3) . ? C9 C1 1.556(3) 2_565 ? C12 C13 1.513(4) . ? C13 C14 1.389(4) . ? C13 C15 1.392(3) 2_565 ? C14 C15 1.381(4) . ? C15 C13 1.392(3) 2_565 ? 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 O3 C1 96.8(2) . 2_565 ? C5 N1 C6 113.5(2) . . ? C5 N1 C12 123.0(2) . . ? C6 N1 C12 122.7(2) . . ? O3 C1 C11 108.06(17) . . ? O3 C1 C2 103.89(15) . . ? C11 C1 C2 116.04(18) . . ? O3 C1 C9 103.99(15) . 2_565 ? C11 C1 C9 116.93(18) . 2_565 ? C2 C1 C9 106.50(17) . 2_565 ? C3 C2 C1 118.3(2) . . ? C3 C2 C9 102.80(16) . . ? C1 C2 C9 100.91(15) . . ? C10 C3 C4 99.7(2) . . ? C10 C3 C2 103.52(19) . . ? C4 C3 C2 108.5(2) . . ? C5 C4 C7 105.3(2) . . ? C5 C4 C3 116.62(19) . . ? C7 C4 C3 103.5(2) . . ? O1 C5 N1 123.9(3) . . ? O1 C5 C4 127.8(3) . . ? N1 C5 C4 108.2(2) . . ? O2 C6 N1 124.1(3) . . ? O2 C6 C7 128.2(2) . . ? N1 C6 C7 107.7(2) . . ? C6 C7 C4 105.1(2) . . ? C6 C7 C8 117.26(19) . . ? C4 C7 C8 103.6(2) . . ? C10 C8 C7 99.47(19) . . ? C10 C8 C9 103.08(18) . . ? C7 C8 C9 108.3(2) . . ? C1 C9 C8 119.10(19) 2_565 . ? C1 C9 C2 100.26(15) 2_565 . ? C8 C9 C2 102.62(15) . . ? C3 C10 C8 94.6(2) . . ? F2 C11 F1 106.3(2) . . ? F2 C11 F3 107.12(18) . . ? F1 C11 F3 107.17(18) . . ? F2 C11 C1 113.48(19) . . ? F1 C11 C1 113.37(19) . . ? F3 C11 C1 109.05(19) . . ? N1 C12 C13 109.9(2) . . ? C14 C13 C15 119.1(2) . 2_565 ? C14 C13 C12 120.1(2) . . ? C15 C13 C12 120.7(2) 2_565 . ? C15 C14 C13 120.9(2) . . ? C14 C15 C13 119.9(2) . 2_565 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.170 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.043 data_k00258 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 F6 N2 O6' _chemical_formula_weight 678.62 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 10.1160(7) _cell_length_b 10.8820(7) _cell_length_c 14.0090(11) _cell_angle_alpha 74.267(4) _cell_angle_beta 79.846(4) _cell_angle_gamma 81.039(4) _cell_volume 1451.60(18) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 11411 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 25.06 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9896 _exptl_absorpt_process_details 'Denzo-SMN, Otwinowski & Minor 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans & \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 11411 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.06 _reflns_number_total 5116 _reflns_number_gt 3671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'Bruker SHELXTL V5.1' _computing_structure_refinement 'Bruker SHELXTL V5.1' _computing_molecular_graphics 'Bruker SHELXTL V5.1' _computing_publication_material 'Bruker SHELXTL V5.1' _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^)+(0.0338P)^2^+1.5114P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0096(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5116 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1435 _refine_ls_wR_factor_gt 0.1292 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.80625(17) 0.62082(16) 0.47591(13) 0.0327(4) Uani 1 1 d . . . F2 F 0.84063(17) 0.47124(16) 0.39886(12) 0.0320(4) Uani 1 1 d . . . F3 F 0.63609(17) 0.54978(17) 0.44277(13) 0.0346(4) Uani 1 1 d . . . F4 F 1.03329(17) 0.32203(18) 0.75939(14) 0.0363(5) Uani 1 1 d . . . F5 F 1.06661(17) 0.17207(17) 0.68316(14) 0.0351(5) Uani 1 1 d . . . F6 F 0.93998(18) 0.14741(18) 0.82690(13) 0.0392(5) Uani 1 1 d . . . O1 O 0.4418(2) 0.1566(2) 0.50492(16) 0.0324(5) Uani 1 1 d . . . O2 O 0.6528(2) -0.1069(2) 0.75947(16) 0.0308(5) Uani 1 1 d . . . O3 O 0.3435(2) 0.6016(2) 0.73235(17) 0.0368(6) Uani 1 1 d . . . O4 O 0.5472(2) 0.3379(2) 0.99100(15) 0.0317(5) Uani 1 1 d . . . O5 O 0.88271(18) 0.37949(18) 0.59886(14) 0.0222(5) Uani 1 1 d . . . N1 N 0.5233(2) 0.0360(2) 0.64956(18) 0.0243(6) Uani 1 1 d . . . N2 N 0.4272(2) 0.4470(2) 0.86196(18) 0.0255(6) Uani 1 1 d . . . C1 C 0.7489(3) 0.4148(3) 0.5710(2) 0.0212(6) Uani 1 1 d . . . C2 C 0.7015(3) 0.2847(3) 0.5728(2) 0.0205(6) Uani 1 1 d . . . H2A H 0.6010 0.2877 0.5900 0.025 Uiso 1 1 calc R . . C3 C 0.7524(3) 0.2226(3) 0.4847(2) 0.0228(6) Uani 1 1 d . . . H3A H 0.7439 0.2814 0.4170 0.027 Uiso 1 1 calc R . . C4 C 0.6846(3) 0.0965(3) 0.5078(2) 0.0260(7) Uani 1 1 d . . . H4A H 0.7017 0.0604 0.4477 0.031 Uiso 1 1 calc R . . C5 C 0.5362(3) 0.1038(3) 0.5494(2) 0.0255(7) Uani 1 1 d . . . C6 C 0.6446(3) -0.0316(3) 0.6786(2) 0.0253(7) Uani 1 1 d . . . C7 C 0.7560(3) 0.0053(3) 0.5934(2) 0.0254(7) Uani 1 1 d . . . H7A H 0.8051 -0.0724 0.5725 0.030 Uiso 1 1 calc R . . C8 C 0.8575(3) 0.0882(3) 0.6110(2) 0.0246(7) Uani 1 1 d . . . H8A H 0.9346 0.0383 0.6459 0.030 Uiso 1 1 calc R . . C9 C 0.7736(3) 0.1916(3) 0.6609(2) 0.0208(6) Uani 1 1 d . . . H9A H 0.7055 0.1522 0.7174 0.025 Uiso 1 1 calc R . . C10 C 0.8465(3) 0.2874(3) 0.6918(2) 0.0221(6) Uani 1 1 d . . . C11 C 0.7337(3) 0.3636(3) 0.7504(2) 0.0215(6) Uani 1 1 d . . . H11A H 0.6697 0.3052 0.7966 0.026 Uiso 1 1 calc R . . C12 C 0.7723(3) 0.4574(3) 0.8039(2) 0.0254(7) Uani 1 1 d . . . H12A H 0.8458 0.4215 0.8464 0.031 Uiso 1 1 calc R . . C13 C 0.6392(3) 0.5137(3) 0.8583(2) 0.0271(7) Uani 1 1 d . . . H13A H 0.6595 0.5632 0.9036 0.032 Uiso 1 1 calc R . . C14 C 0.5381(3) 0.4205(3) 0.9141(2) 0.0251(7) Uani 1 1 d . . . C15 C 0.4337(3) 0.5569(3) 0.7823(2) 0.0271(7) Uani 1 1 d . . . C16 C 0.5685(3) 0.6047(3) 0.7723(2) 0.0266(7) Uani 1 1 d . . . H16A H 0.5562 0.6952 0.7788 0.032 Uiso 1 1 calc R . . C17 C 0.6686(3) 0.5913(3) 0.6766(2) 0.0242(7) Uani 1 1 d . . . H17A H 0.6579 0.6641 0.6160 0.029 Uiso 1 1 calc R . . C18 C 0.6625(3) 0.4568(3) 0.6619(2) 0.0200(6) Uani 1 1 d . . . H18A H 0.5666 0.4398 0.6681 0.024 Uiso 1 1 calc R . . C19 C 0.8031(3) 0.5758(3) 0.7176(2) 0.0302(7) Uani 1 1 d . . . H19A H 0.8146 0.6506 0.7415 0.036 Uiso 1 1 calc R . . H19B H 0.8823 0.5573 0.6689 0.036 Uiso 1 1 calc R . . C20 C 0.8977(3) 0.1647(3) 0.5019(2) 0.0263(7) Uani 1 1 d . . . H20A H 0.9574 0.2308 0.4970 0.032 Uiso 1 1 calc R . . H20B H 0.9389 0.1085 0.4570 0.032 Uiso 1 1 calc R . . C21 C 0.9726(3) 0.2329(3) 0.7397(2) 0.0280(7) Uani 1 1 d . . . C22 C 0.7592(3) 0.5144(3) 0.4720(2) 0.0240(7) Uani 1 1 d . . . C23 C 0.3917(3) 0.0202(3) 0.7128(2) 0.0286(7) Uani 1 1 d . . . H23A H 0.3778 -0.0718 0.7313 0.034 Uiso 1 1 calc R . . H23B H 0.3198 0.0683 0.6730 0.034 Uiso 1 1 calc R . . C24 C 0.3759(3) 0.0654(3) 0.8076(2) 0.0245(7) Uani 1 1 d . . . C25 C 0.3692(3) -0.0247(3) 0.8996(2) 0.0334(8) Uani 1 1 d . . . H25A H 0.3825 -0.1137 0.9018 0.040 Uiso 1 1 calc R . . C26 C 0.3433(3) 0.0142(3) 0.9880(2) 0.0374(8) Uani 1 1 d . . . H26A H 0.3370 -0.0482 1.0505 0.045 Uiso 1 1 calc R . . C27 C 0.3267(3) 0.1439(3) 0.9857(2) 0.0330(8) Uani 1 1 d . . . H27A H 0.3095 0.1700 1.0466 0.040 Uiso 1 1 calc R . . C28 C 0.3350(3) 0.2359(3) 0.8946(2) 0.0260(7) Uani 1 1 d . . . C29 C 0.3588(3) 0.1960(3) 0.8061(2) 0.0248(7) Uani 1 1 d . . . H29A H 0.3636 0.2585 0.7436 0.030 Uiso 1 1 calc R . . C30 C 0.3076(3) 0.3770(3) 0.8937(2) 0.0284(7) Uani 1 1 d . . . H30A H 0.2400 0.4188 0.8482 0.034 Uiso 1 1 calc R . . H30B H 0.2674 0.3847 0.9618 0.034 Uiso 1 1 calc R . . C1S C 0.9611(7) 0.3369(6) 1.0305(4) 0.101(2) Uani 1 1 d . . . H1SA H 0.8890 0.4101 1.0204 0.121 Uiso 1 1 calc R . . H1SB H 1.0237 0.3431 0.9670 0.121 Uiso 1 1 calc R . . O1S O 1.0320(5) 0.3421(4) 1.1075(3) 0.1051(14) Uani 1 1 d . . . C3S C 0.8970(5) 0.1721(5) 1.1659(4) 0.0815(16) Uani 1 1 d . . . H3SA H 0.8041 0.1900 1.1996 0.098 Uiso 1 1 calc R . . H3SB H 0.9240 0.0782 1.1828 0.098 Uiso 1 1 calc R . . C4S C 0.9915(5) 0.2396(5) 1.1938(4) 0.0724(14) Uani 1 1 d . . . H4SA H 0.9480 0.2759 1.2509 0.087 Uiso 1 1 calc R . . H4SB H 1.0716 0.1796 1.2143 0.087 Uiso 1 1 calc R . . C2S C 0.9065(9) 0.2256(9) 1.0563(4) 0.156(4) Uani 1 1 d . . . H2SA H 0.9632 0.1637 1.0214 0.187 Uiso 1 1 calc R . . H2SB H 0.8153 0.2405 1.0359 0.187 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 0.0384(10) 0.0224(9) 0.0356(10) -0.0040(8) 0.0001(8) -0.0102(8) F2 0.0360(10) 0.0308(10) 0.0255(9) -0.0047(8) 0.0041(8) -0.0064(8) F3 0.0281(10) 0.0369(11) 0.0334(10) 0.0028(8) -0.0098(8) -0.0021(8) F4 0.0262(9) 0.0401(11) 0.0485(12) -0.0149(9) -0.0136(8) -0.0050(8) F5 0.0221(9) 0.0366(11) 0.0452(11) -0.0119(9) -0.0059(8) 0.0054(8) F6 0.0345(10) 0.0434(12) 0.0321(10) 0.0058(9) -0.0105(8) -0.0027(9) O1 0.0346(13) 0.0272(12) 0.0381(13) -0.0076(10) -0.0150(11) -0.0020(10) O2 0.0358(12) 0.0237(11) 0.0313(13) -0.0030(10) -0.0064(10) -0.0038(10) O3 0.0308(12) 0.0421(14) 0.0337(13) -0.0075(11) -0.0074(10) 0.0069(11) O4 0.0390(13) 0.0296(12) 0.0251(12) -0.0044(10) -0.0065(10) -0.0015(10) O5 0.0178(10) 0.0237(11) 0.0230(11) -0.0024(9) -0.0040(8) -0.0010(8) N1 0.0238(13) 0.0214(13) 0.0291(14) -0.0082(11) -0.0052(11) -0.0021(11) N2 0.0247(13) 0.0255(14) 0.0282(14) -0.0106(11) -0.0034(11) -0.0020(11) C1 0.0168(14) 0.0227(15) 0.0244(15) -0.0070(13) -0.0032(12) -0.0007(12) C2 0.0184(14) 0.0195(15) 0.0219(15) -0.0042(12) -0.0018(12) -0.0004(12) C3 0.0277(16) 0.0198(15) 0.0202(15) -0.0061(12) -0.0004(12) -0.0016(12) C4 0.0315(16) 0.0208(15) 0.0272(16) -0.0101(13) -0.0052(13) 0.0008(13) C5 0.0334(17) 0.0174(15) 0.0285(17) -0.0087(13) -0.0070(14) -0.0030(13) C6 0.0304(16) 0.0166(15) 0.0329(18) -0.0105(14) -0.0072(13) -0.0040(13) C7 0.0267(16) 0.0207(15) 0.0286(17) -0.0103(13) -0.0004(13) 0.0009(13) C8 0.0222(15) 0.0202(15) 0.0297(17) -0.0053(13) -0.0040(13) 0.0012(12) C9 0.0196(14) 0.0216(15) 0.0216(15) -0.0068(12) -0.0030(12) -0.0014(12) C10 0.0231(15) 0.0218(15) 0.0204(15) -0.0021(12) -0.0045(12) -0.0035(12) C11 0.0230(15) 0.0206(15) 0.0219(15) -0.0041(12) -0.0060(12) -0.0048(12) C12 0.0256(15) 0.0249(16) 0.0291(16) -0.0102(13) -0.0058(13) -0.0045(13) C13 0.0304(16) 0.0263(16) 0.0295(17) -0.0141(14) -0.0049(13) -0.0047(13) C14 0.0310(16) 0.0257(16) 0.0217(16) -0.0140(14) -0.0037(13) 0.0020(13) C15 0.0316(17) 0.0260(16) 0.0244(16) -0.0124(14) -0.0019(14) 0.0033(14) C16 0.0322(17) 0.0195(15) 0.0299(17) -0.0110(13) -0.0027(13) -0.0020(13) C17 0.0295(16) 0.0166(15) 0.0258(16) -0.0048(12) -0.0024(13) -0.0027(12) C18 0.0198(14) 0.0183(15) 0.0212(15) -0.0038(12) -0.0033(12) -0.0020(12) C19 0.0312(17) 0.0273(17) 0.0352(18) -0.0109(15) -0.0025(14) -0.0100(14) C20 0.0250(15) 0.0242(16) 0.0286(17) -0.0106(13) 0.0023(13) 0.0003(13) C21 0.0275(16) 0.0298(17) 0.0257(17) -0.0055(14) -0.0046(13) -0.0020(14) C22 0.0202(15) 0.0263(16) 0.0258(16) -0.0083(13) -0.0021(12) -0.0012(12) C23 0.0254(16) 0.0297(17) 0.0336(18) -0.0120(14) -0.0028(13) -0.0064(13) C24 0.0206(15) 0.0272(16) 0.0280(16) -0.0090(14) -0.0027(12) -0.0066(13) C25 0.0340(18) 0.0258(17) 0.041(2) -0.0072(15) -0.0057(15) -0.0062(14) C26 0.043(2) 0.0369(19) 0.0282(18) 0.0038(15) -0.0053(15) -0.0117(16) C27 0.0338(18) 0.042(2) 0.0238(17) -0.0077(15) 0.0010(14) -0.0119(15) C28 0.0191(14) 0.0323(18) 0.0274(17) -0.0090(14) -0.0002(12) -0.0062(13) C29 0.0198(14) 0.0288(17) 0.0250(16) -0.0059(13) -0.0022(12) -0.0030(12) C30 0.0237(16) 0.0324(18) 0.0313(17) -0.0132(14) -0.0002(13) -0.0040(13) C1S 0.145(5) 0.106(4) 0.064(3) 0.025(3) -0.067(3) -0.076(4) O1S 0.157(4) 0.099(3) 0.074(2) 0.004(2) -0.051(2) -0.064(3) C3S 0.071(3) 0.071(3) 0.107(4) -0.010(3) -0.025(3) -0.031(3) C4S 0.077(3) 0.079(3) 0.062(3) 0.003(3) -0.027(2) -0.028(3) C2S 0.204(8) 0.229(9) 0.067(4) -0.004(5) -0.030(4) -0.168(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 C22 1.336(3) . ? F2 C22 1.339(3) . ? F3 C22 1.346(3) . ? F4 C21 1.336(3) . ? F5 C21 1.339(3) . ? F6 C21 1.343(3) . ? O1 C5 1.215(4) . ? O2 C6 1.212(4) . ? O3 C15 1.208(4) . ? O4 C14 1.209(4) . ? O5 C10 1.440(3) . ? O5 C1 1.440(3) . ? N1 C5 1.390(4) . ? N1 C6 1.395(4) . ? N1 C23 1.470(4) . ? N2 C14 1.396(4) . ? N2 C15 1.398(4) . ? N2 C30 1.468(4) . ? C1 C22 1.509(4) . ? C1 C18 1.547(4) . ? C1 C2 1.557(4) . ? C2 C3 1.538(4) . ? C2 C9 1.578(4) . ? C3 C20 1.539(4) . ? C3 C4 1.560(4) . ? C4 C5 1.510(4) . ? C4 C7 1.543(4) . ? C6 C7 1.505(4) . ? C7 C8 1.558(4) . ? C8 C20 1.547(4) . ? C8 C9 1.547(4) . ? C9 C10 1.555(4) . ? C10 C21 1.509(4) . ? C10 C11 1.552(4) . ? C11 C12 1.548(4) . ? C11 C18 1.579(4) . ? C12 C19 1.538(4) . ? C12 C13 1.550(4) . ? C13 C14 1.515(4) . ? C13 C16 1.543(4) . ? C15 C16 1.504(4) . ? C16 C17 1.558(4) . ? C17 C19 1.536(4) . ? C17 C18 1.544(4) . ? C23 C24 1.512(4) . ? C24 C25 1.389(4) . ? C24 C29 1.400(4) . ? C25 C26 1.385(4) . ? C26 C27 1.388(5) . ? C27 C28 1.390(4) . ? C28 C29 1.392(4) . ? C28 C30 1.515(4) . ? C1S C2S 1.343(7) . ? C1S O1S 1.413(5) . ? O1S C4S 1.453(5) . ? C3S C4S 1.454(6) . ? C3S C2S 1.479(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 C10 O5 C1 96.99(19) . . ? C5 N1 C6 113.1(2) . . ? C5 N1 C23 122.8(3) . . ? C6 N1 C23 123.3(3) . . ? C14 N2 C15 113.2(2) . . ? C14 N2 C30 124.0(3) . . ? C15 N2 C30 122.4(3) . . ? O5 C1 C22 107.6(2) . . ? O5 C1 C18 104.4(2) . . ? C22 C1 C18 117.0(2) . . ? O5 C1 C2 104.1(2) . . ? C22 C1 C2 117.0(2) . . ? C18 C1 C2 105.3(2) . . ? C3 C2 C1 119.8(2) . . ? C3 C2 C9 103.2(2) . . ? C1 C2 C9 100.5(2) . . ? C2 C3 C20 103.4(2) . . ? C2 C3 C4 107.4(2) . . ? C20 C3 C4 99.6(2) . . ? C5 C4 C7 104.9(2) . . ? C5 C4 C3 116.6(2) . . ? C7 C4 C3 103.7(2) . . ? O1 C5 N1 124.4(3) . . ? O1 C5 C4 127.4(3) . . ? N1 C5 C4 108.2(3) . . ? O2 C6 N1 123.6(3) . . ? O2 C6 C7 128.3(3) . . ? N1 C6 C7 108.2(3) . . ? C6 C7 C4 105.1(2) . . ? C6 C7 C8 115.7(2) . . ? C4 C7 C8 103.5(2) . . ? C20 C8 C9 103.2(2) . . ? C20 C8 C7 99.6(2) . . ? C9 C8 C7 107.2(2) . . ? C8 C9 C10 119.8(2) . . ? C8 C9 C2 102.9(2) . . ? C10 C9 C2 100.9(2) . . ? O5 C10 C21 108.6(2) . . ? O5 C10 C11 104.0(2) . . ? C21 C10 C11 116.9(2) . . ? O5 C10 C9 103.8(2) . . ? C21 C10 C9 116.7(2) . . ? C11 C10 C9 105.3(2) . . ? C12 C11 C10 119.6(2) . . ? C12 C11 C18 102.9(2) . . ? C10 C11 C18 100.9(2) . . ? C19 C12 C11 103.2(2) . . ? C19 C12 C13 99.6(2) . . ? C11 C12 C13 107.1(2) . . ? C14 C13 C16 104.8(2) . . ? C14 C13 C12 116.9(2) . . ? C16 C13 C12 103.8(2) . . ? O4 C14 N2 124.3(3) . . ? O4 C14 C13 127.7(3) . . ? N2 C14 C13 108.0(3) . . ? O3 C15 N2 123.6(3) . . ? O3 C15 C16 128.3(3) . . ? N2 C15 C16 108.1(3) . . ? C15 C16 C13 105.5(2) . . ? C15 C16 C17 115.6(2) . . ? C13 C16 C17 103.5(2) . . ? C19 C17 C18 103.1(2) . . ? C19 C17 C16 99.5(2) . . ? C18 C17 C16 107.3(2) . . ? C17 C18 C1 120.0(2) . . ? C17 C18 C11 103.1(2) . . ? C1 C18 C11 100.6(2) . . ? C17 C19 C12 95.5(2) . . ? C3 C20 C8 95.0(2) . . ? F4 C21 F5 106.0(2) . . ? F4 C21 F6 107.5(2) . . ? F5 C21 F6 107.4(2) . . ? F4 C21 C10 113.2(2) . . ? F5 C21 C10 113.2(2) . . ? F6 C21 C10 109.2(2) . . ? F1 C22 F2 106.3(2) . . ? F1 C22 F3 107.3(2) . . ? F2 C22 F3 107.3(2) . . ? F1 C22 C1 113.2(2) . . ? F2 C22 C1 112.8(2) . . ? F3 C22 C1 109.7(2) . . ? N1 C23 C24 114.6(2) . . ? C25 C24 C29 118.7(3) . . ? C25 C24 C23 119.2(3) . . ? C29 C24 C23 121.9(3) . . ? C26 C25 C24 120.6(3) . . ? C25 C26 C27 120.2(3) . . ? C26 C27 C28 120.3(3) . . ? C27 C28 C29 119.1(3) . . ? C27 C28 C30 119.4(3) . . ? C29 C28 C30 121.3(3) . . ? C28 C29 C24 121.0(3) . . ? N2 C30 C28 114.7(2) . . ? C2S C1S O1S 109.2(5) . . ? C1S O1S C4S 106.6(3) . . ? C4S C3S C2S 102.9(4) . . ? O1S C4S C3S 108.0(4) . . ? C1S C2S C3S 109.5(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.677 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.058 data_k00145 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 F6 N2 O5' _chemical_formula_weight 504.38 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(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.7369(6) _cell_length_b 7.7697(4) _cell_length_c 20.4778(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.483(2) _cell_angle_gamma 90.00 _cell_volume 2072.89(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 10968 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 27.49 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9495 _exptl_absorpt_correction_T_max 0.9823 _exptl_absorpt_process_details 'Denzo-SMN, Otwinowski & Minor 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 10968 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4696 _reflns_number_gt 3168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'Bruker SHELXTL V5.1' _computing_structure_refinement 'Bruker SHELXTL V5.1' _computing_molecular_graphics 'Bruker SHELXTL V5.1' _computing_publication_material 'Bruker SHELXTL V5.1' _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^)+(0.0480P)^2^+0.3683P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4696 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C1 C 0.34932(14) 0.4094(3) 0.30172(9) 0.0179(5) Uani 1 1 d . . . C2 C 0.28425(14) 0.4871(3) 0.23107(9) 0.0178(5) Uani 1 1 d . . . H2A H 0.2683 0.6113 0.2355 0.021 Uiso 1 1 calc R . . C3 C 0.32048(15) 0.4555(3) 0.16763(9) 0.0194(5) Uani 1 1 d . . . H3A H 0.3942 0.4842 0.1750 0.023 Uiso 1 1 calc R . . C4 C 0.24366(15) 0.5407(3) 0.10325(9) 0.0195(5) Uani 1 1 d . . . H4A H 0.2711 0.5325 0.0636 0.023 Uiso 1 1 calc R . . C5 C 0.20632(15) 0.7223(3) 0.10789(9) 0.0202(5) Uani 1 1 d . . . N6 N 0.10147(12) 0.7118(2) 0.10067(8) 0.0217(4) Uani 1 1 d . . . H6A H 0.0641 0.8024 0.1028 0.026 Uiso 1 1 calc R . . C7 C 0.06240(16) 0.5485(3) 0.09003(9) 0.0202(5) Uani 1 1 d . . . C8 C 0.14677(14) 0.4261(3) 0.08904(9) 0.0185(5) Uani 1 1 d . . . H8A H 0.1306 0.3718 0.0425 0.022 Uiso 1 1 calc R . . C9 C 0.17866(15) 0.2866(3) 0.14536(9) 0.0187(5) Uani 1 1 d . . . H9A H 0.1372 0.1784 0.1346 0.022 Uiso 1 1 calc R . . C10 C 0.18475(15) 0.3715(3) 0.21511(9) 0.0172(5) Uani 1 1 d . . . H10A H 0.1225 0.4429 0.2110 0.021 Uiso 1 1 calc R . . C11 C 0.21239(14) 0.2554(3) 0.28050(9) 0.0176(5) Uani 1 1 d . . . C12 C 0.20232(14) 0.3693(3) 0.34058(9) 0.0167(5) Uani 1 1 d . . . H12A H 0.1391 0.4422 0.3255 0.020 Uiso 1 1 calc R . . C13 C 0.21521(15) 0.2832(3) 0.41128(9) 0.0191(5) Uani 1 1 d . . . H13A H 0.1733 0.1768 0.4091 0.023 Uiso 1 1 calc R . . C14 C 0.20026(15) 0.4242(3) 0.46074(9) 0.0182(5) Uani 1 1 d . . . H14A H 0.1966 0.3700 0.5042 0.022 Uiso 1 1 calc R . . C15 C 0.11329(16) 0.5492(3) 0.43393(9) 0.0198(5) Uani 1 1 d . . . N16 N 0.15322(13) 0.7111(2) 0.43455(8) 0.0215(4) Uani 1 1 d . . . H16A H 0.1149 0.8034 0.4214 0.026 Uiso 1 1 calc R . . C17 C 0.26063(16) 0.7161(3) 0.45811(9) 0.0204(5) Uani 1 1 d . . . C18 C 0.29816(15) 0.5350(3) 0.47627(9) 0.0197(5) Uani 1 1 d . . . H18A H 0.3381 0.5278 0.5264 0.024 Uiso 1 1 calc R . . C19 C 0.35891(15) 0.4468(3) 0.43327(9) 0.0192(5) Uani 1 1 d . . . H19A H 0.4340 0.4730 0.4488 0.023 Uiso 1 1 calc R . . C20 C 0.30293(14) 0.4828(3) 0.35609(9) 0.0183(5) Uani 1 1 d . . . H20A H 0.2858 0.6076 0.3478 0.022 Uiso 1 1 calc R . . O21 O 0.32097(10) 0.22991(19) 0.29701(6) 0.0190(3) Uani 1 1 d . . . C22 C 0.33235(15) 0.2569(3) 0.44193(10) 0.0211(5) Uani 1 1 d . . . H22A H 0.3539 0.2199 0.4907 0.025 Uiso 1 1 calc R . . H22B H 0.3598 0.1770 0.4144 0.025 Uiso 1 1 calc R . . C23 C 0.29260(15) 0.2655(3) 0.15058(10) 0.0200(5) Uani 1 1 d . . . H23A H 0.3301 0.1867 0.1881 0.024 Uiso 1 1 calc R . . H23B H 0.3018 0.2292 0.1066 0.024 Uiso 1 1 calc R . . C24 C 0.46504(16) 0.4183(3) 0.32120(10) 0.0253(5) Uani 1 1 d . . . F25 F 0.49566(9) 0.5813(2) 0.33328(7) 0.0408(4) Uani 1 1 d . . . F26 F 0.50146(9) 0.3566(2) 0.27266(6) 0.0380(4) Uani 1 1 d . . . F27 F 0.51206(8) 0.32742(19) 0.37812(6) 0.0328(4) Uani 1 1 d . . . C28 C 0.16057(15) 0.0812(3) 0.27228(9) 0.0215(5) Uani 1 1 d . . . F29 F 0.05868(9) 0.10213(19) 0.25650(6) 0.0359(4) Uani 1 1 d . . . F30 F 0.17685(10) -0.01537(17) 0.22273(6) 0.0312(3) Uani 1 1 d . . . F31 F 0.19146(10) -0.01513(18) 0.32902(6) 0.0327(3) Uani 1 1 d . . . O32 O 0.25326(11) 0.8551(2) 0.11408(7) 0.0284(4) Uani 1 1 d . . . O33 O -0.02764(10) 0.5133(2) 0.08157(7) 0.0248(4) Uani 1 1 d . . . O34 O 0.31051(11) 0.8460(2) 0.46353(7) 0.0291(4) Uani 1 1 d . . . O35 O 0.02119(11) 0.5173(2) 0.41442(7) 0.0270(4) 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 C1 0.0164(10) 0.0195(13) 0.0170(10) -0.0025(9) 0.0041(8) -0.0033(9) C2 0.0176(10) 0.0204(13) 0.0156(10) -0.0003(9) 0.0057(8) -0.0012(9) C3 0.0158(10) 0.0258(14) 0.0167(10) -0.0013(9) 0.0053(7) 0.0000(9) C4 0.0200(11) 0.0253(14) 0.0142(9) 0.0012(9) 0.0067(8) 0.0022(10) C5 0.0234(11) 0.0265(15) 0.0115(9) -0.0004(9) 0.0066(8) -0.0005(10) N6 0.0206(9) 0.0189(11) 0.0261(9) 0.0000(8) 0.0082(7) 0.0026(8) C7 0.0233(12) 0.0239(14) 0.0117(9) 0.0005(9) 0.0033(8) 0.0017(10) C8 0.0194(10) 0.0205(13) 0.0145(9) -0.0020(9) 0.0041(8) 0.0037(9) C9 0.0190(10) 0.0197(13) 0.0155(10) -0.0019(9) 0.0028(7) 0.0014(9) C10 0.0170(10) 0.0194(12) 0.0152(9) -0.0010(9) 0.0049(7) 0.0001(9) C11 0.0142(10) 0.0211(13) 0.0159(10) -0.0003(9) 0.0023(7) -0.0004(9) C12 0.0159(10) 0.0187(12) 0.0155(10) -0.0013(9) 0.0049(7) -0.0029(9) C13 0.0216(11) 0.0183(13) 0.0165(10) -0.0001(9) 0.0049(8) -0.0018(9) C14 0.0205(10) 0.0203(13) 0.0140(9) 0.0040(9) 0.0057(8) -0.0005(9) C15 0.0255(12) 0.0216(13) 0.0124(9) 0.0010(9) 0.0061(8) 0.0005(10) N16 0.0234(10) 0.0174(11) 0.0228(9) 0.0018(8) 0.0058(7) 0.0020(8) C17 0.0256(11) 0.0247(14) 0.0109(9) -0.0022(9) 0.0056(8) -0.0023(10) C18 0.0213(11) 0.0242(14) 0.0120(9) 0.0006(9) 0.0030(8) -0.0022(10) C19 0.0174(10) 0.0233(13) 0.0151(9) -0.0009(9) 0.0027(8) -0.0011(9) C20 0.0173(10) 0.0211(13) 0.0155(9) 0.0002(9) 0.0035(7) -0.0019(9) O21 0.0154(7) 0.0213(9) 0.0194(7) 0.0003(6) 0.0041(5) 0.0017(6) C22 0.0215(11) 0.0240(14) 0.0157(10) 0.0026(10) 0.0028(8) 0.0020(10) C23 0.0209(11) 0.0233(13) 0.0150(10) 0.0004(9) 0.0047(8) 0.0048(10) C24 0.0224(11) 0.0337(16) 0.0187(11) -0.0001(10) 0.0047(9) -0.0015(11) F25 0.0262(7) 0.0421(11) 0.0526(9) -0.0040(8) 0.0107(6) -0.0148(7) F26 0.0216(7) 0.0700(12) 0.0239(7) -0.0017(7) 0.0091(5) 0.0091(7) F27 0.0191(6) 0.0538(11) 0.0217(6) 0.0040(6) 0.0011(5) 0.0047(6) C28 0.0251(11) 0.0218(14) 0.0160(10) 0.0007(10) 0.0045(8) -0.0019(10) F29 0.0240(7) 0.0335(10) 0.0481(8) -0.0027(7) 0.0083(6) -0.0088(6) F30 0.0495(8) 0.0218(8) 0.0233(6) -0.0061(6) 0.0128(6) -0.0038(7) F31 0.0530(9) 0.0217(8) 0.0212(6) 0.0033(6) 0.0086(6) -0.0049(7) O32 0.0305(9) 0.0257(10) 0.0319(9) -0.0020(8) 0.0138(7) -0.0062(8) O33 0.0191(8) 0.0238(10) 0.0288(8) -0.0008(7) 0.0041(6) -0.0009(7) O34 0.0337(9) 0.0249(11) 0.0273(8) -0.0048(7) 0.0077(7) -0.0105(8) O35 0.0210(8) 0.0252(10) 0.0334(8) -0.0006(7) 0.0064(6) -0.0013(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O21 1.443(3) . ? C1 C24 1.513(3) . ? C1 C20 1.556(3) . ? C1 C2 1.561(3) . ? C2 C3 1.551(3) . ? C2 C10 1.581(3) . ? C3 C23 1.537(3) . ? C3 C4 1.552(3) . ? C4 C5 1.514(3) . ? C4 C8 1.550(3) . ? C5 O32 1.202(3) . ? C5 N6 1.403(2) . ? N6 C7 1.368(3) . ? N6 N16 6.646(2) . ? C7 O33 1.224(2) . ? C7 C8 1.504(3) . ? C8 C9 1.542(3) . ? C9 C23 1.543(3) . ? C9 C10 1.551(3) . ? C10 C11 1.558(3) . ? C11 O21 1.435(2) . ? C11 C28 1.514(3) . ? C11 C12 1.557(3) . ? C12 C13 1.553(3) . ? C12 C20 1.584(3) . ? C13 C22 1.544(3) . ? C13 C14 1.549(3) . ? C14 C15 1.502(3) . ? C14 C18 1.543(3) . ? C15 O35 1.225(2) . ? C15 N16 1.371(3) . ? N16 C17 1.400(3) . ? C17 O34 1.205(3) . ? C17 C18 1.504(3) . ? C18 C19 1.552(3) . ? C19 C22 1.543(3) . ? C19 C20 1.548(2) . ? C24 F25 1.333(3) . ? C24 F26 1.335(2) . ? C24 F27 1.341(2) . ? C28 F31 1.333(2) . ? C28 F30 1.337(2) . ? C28 F29 1.343(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 O21 C1 C24 107.48(18) . . ? O21 C1 C20 103.82(15) . . ? C24 C1 C20 115.42(16) . . ? O21 C1 C2 104.39(15) . . ? C24 C1 C2 118.15(16) . . ? C20 C1 C2 106.12(16) . . ? C3 C2 C1 118.27(17) . . ? C3 C2 C10 102.88(15) . . ? C1 C2 C10 100.11(15) . . ? C23 C3 C2 102.67(16) . . ? C23 C3 C4 99.42(16) . . ? C2 C3 C4 109.36(16) . . ? C5 C4 C8 105.02(16) . . ? C5 C4 C3 119.80(17) . . ? C8 C4 C3 103.08(16) . . ? O32 C5 N6 124.0(2) . . ? O32 C5 C4 128.70(19) . . ? N6 C5 C4 107.25(19) . . ? C7 N6 C5 114.09(19) . . ? C7 N6 N16 94.11(11) . . ? C5 N6 N16 96.90(10) . . ? O33 C7 N6 123.9(2) . . ? O33 C7 C8 127.2(2) . . ? N6 C7 C8 108.88(17) . . ? C7 C8 C9 118.16(16) . . ? C7 C8 C4 104.68(18) . . ? C9 C8 C4 103.90(15) . . ? C8 C9 C23 99.66(16) . . ? C8 C9 C10 108.02(17) . . ? C23 C9 C10 102.94(15) . . ? C9 C10 C11 118.19(18) . . ? C9 C10 C2 102.87(15) . . ? C11 C10 C2 101.07(14) . . ? O21 C11 C28 108.66(18) . . ? O21 C11 C12 103.80(14) . . ? C28 C11 C12 116.07(16) . . ? O21 C11 C10 103.55(15) . . ? C28 C11 C10 116.36(15) . . ? C12 C11 C10 106.96(17) . . ? C13 C12 C11 118.66(18) . . ? C13 C12 C20 102.61(14) . . ? C11 C12 C20 100.62(14) . . ? C22 C13 C14 99.49(15) . . ? C22 C13 C12 103.41(15) . . ? C14 C13 C12 107.78(17) . . ? C15 C14 C18 104.78(18) . . ? C15 C14 C13 118.24(16) . . ? C18 C14 C13 103.99(15) . . ? O35 C15 N16 123.9(2) . . ? O35 C15 C14 127.5(2) . . ? N16 C15 C14 108.69(17) . . ? C15 N16 C17 113.79(19) . . ? C15 N16 N6 94.54(11) . . ? C17 N16 N6 96.42(10) . . ? O34 C17 N16 124.2(2) . . ? O34 C17 C18 128.34(19) . . ? N16 C17 C18 107.48(18) . . ? C17 C18 C14 105.25(16) . . ? C17 C18 C19 118.47(17) . . ? C14 C18 C19 103.13(17) . . ? C22 C19 C20 103.36(16) . . ? C22 C19 C18 99.65(16) . . ? C20 C19 C18 108.49(16) . . ? C19 C20 C1 118.74(17) . . ? C19 C20 C12 102.92(15) . . ? C1 C20 C12 100.48(15) . . ? C11 O21 C1 96.93(15) . . ? C19 C22 C13 94.63(17) . . ? C3 C23 C9 95.05(16) . . ? F25 C24 F26 107.97(18) . . ? F25 C24 F27 107.60(17) . . ? F26 C24 F27 105.51(19) . . ? F25 C24 C1 109.62(19) . . ? F26 C24 C1 113.44(17) . . ? F27 C24 C1 112.43(17) . . ? F31 C28 F30 105.24(18) . . ? F31 C28 F29 107.28(16) . . ? F30 C28 F29 107.34(16) . . ? F31 C28 C11 113.35(16) . . ? F30 C28 C11 113.60(16) . . ? F29 C28 C11 109.64(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N6 H6A O35 0.88 2.01 2.870(2) 167.0 2 N16 H16A O33 0.88 2.01 2.870(2) 164.1 2 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.455 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.064