# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name ; D. O'Hagan ; 'Martin Schuler' 'A. Slawin' _publ_contact_author_name ; Prof D O'Hagan ; _publ_contact_author_address ; School of Chemistry University of St Andrews Purdie Building North Haugh St Andrews Fife KY16 9ST ; _publ_contact_author_email DO1@ST-ANDREWS.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; The C-F bond as a tool for influencing peptide conformation ; data_5a _database_code_depnum_ccdc_archive 'CCDC 271257' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 F2 N2 O6.(C Cl4)0.25' _chemical_formula_sum 'C22.25 H22 Cl F2 N2 O6' _chemical_formula_weight 486.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.9826(19) _cell_length_b 22.066(10) _cell_length_c 24.319(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2673.7(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2703 _cell_measurement_theta_min 2.0045 _cell_measurement_theta_max 68.2478 _exptl_crystal_description needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.3000 _exptl_crystal_size_mid 0.0200 _exptl_crystal_size_min 0.0100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1010 _exptl_absorpt_coefficient_mu 1.709 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2037 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type ccd _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35848 _diffrn_reflns_av_R_equivalents 0.1355 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 7.56 _diffrn_reflns_theta_max 67.99 _reflns_number_total 4760 _reflns_number_gt 3882 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0059(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.23(13) _refine_ls_number_reflns 4760 _refine_ls_number_parameters 347 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1414 _refine_ls_R_factor_gt 0.1260 _refine_ls_wR_factor_ref 0.3451 _refine_ls_wR_factor_gt 0.3296 _refine_ls_goodness_of_fit_ref 1.347 _refine_ls_restrained_S_all 1.345 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.004 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 0.8030(14) 0.6857(3) 0.9280(3) 0.0690(16) Uani 1 1 d . . . H1A H 0.9958 0.6778 0.9212 0.083 Uiso 1 1 calc R . . H1B H 0.7867 0.7058 0.9642 0.083 Uiso 1 1 calc R . . C2 C 0.6987(11) 0.7280(3) 0.8840(2) 0.0588(14) Uani 1 1 d . . . H2A H 0.5076 0.7370 0.8936 0.071 Uiso 1 1 calc R . . N3 N 0.6972(8) 0.7036(2) 0.82939(19) 0.0527(11) Uani 1 1 d D . . H3N H 0.881(4) 0.694(2) 0.818(2) 0.044(13) Uiso 1 1 d D . . C4 C 0.4746(10) 0.6844(3) 0.8040(3) 0.0545(13) Uani 1 1 d . . . O4 O 0.2488(7) 0.6889(3) 0.8223(2) 0.0787(15) Uani 1 1 d . . . C5 C 0.5105(11) 0.6560(3) 0.7479(3) 0.0562(13) Uani 1 1 d . . . H5A H 0.3565 0.6687 0.7242 0.067 Uiso 1 1 calc R . . F5 F 0.7479(8) 0.67582(19) 0.72315(16) 0.0823(12) Uani 1 1 d . . . C6 C 0.5191(12) 0.5883(3) 0.7493(3) 0.0591(14) Uani 1 1 d . . . H6A H 0.3755 0.5737 0.7747 0.071 Uiso 1 1 calc R . . F6 F 0.7695(8) 0.57082(19) 0.77084(14) 0.0752(11) Uani 1 1 d . . . C7 C 0.4722(11) 0.5596(3) 0.6926(3) 0.0572(14) Uani 1 1 d . . . O7 O 0.2436(8) 0.5611(2) 0.67475(19) 0.0749(14) Uani 1 1 d . . . N8 N 0.6829(9) 0.5337(2) 0.66854(19) 0.0556(11) Uani 1 1 d D . . H8N H 0.858(6) 0.537(3) 0.686(3) 0.070(19) Uiso 1 1 d D . . C9 C 0.6664(11) 0.5043(3) 0.6153(2) 0.0556(13) Uani 1 1 d . . . H9A H 0.4723 0.4992 0.6059 0.067 Uiso 1 1 calc R . . C10 C 0.7969(13) 0.5422(3) 0.5698(3) 0.0663(16) Uani 1 1 d . . . H10A H 0.9868 0.5495 0.5797 0.080 Uiso 1 1 calc R . . H10B H 0.7950 0.5184 0.5353 0.080 Uiso 1 1 calc R . . C11 C 0.6660(12) 0.6011(3) 0.5596(2) 0.0615(15) Uani 1 1 d . . . C12 C 0.4606(16) 0.6085(4) 0.5217(3) 0.077(2) Uani 1 1 d . . . H12A H 0.4084 0.5748 0.4999 0.093 Uiso 1 1 calc R . . C13 C 0.3301(18) 0.6625(4) 0.5145(4) 0.096(3) Uani 1 1 d . . . H13A H 0.1905 0.6656 0.4881 0.115 Uiso 1 1 calc R . . C14 C 0.3994(16) 0.7119(4) 0.5452(4) 0.085(2) Uani 1 1 d . . . H14A H 0.3082 0.7493 0.5401 0.102 Uiso 1 1 calc R . . C15 C 0.6088(17) 0.7072(3) 0.5849(3) 0.083(2) Uani 1 1 d . . . H15A H 0.6599 0.7416 0.6060 0.099 Uiso 1 1 calc R . . C16 C 0.7357(15) 0.6529(3) 0.5925(3) 0.0694(16) Uani 1 1 d . . . H16A H 0.8713 0.6494 0.6198 0.083 Uiso 1 1 calc R . . C17 C 0.6572(12) 0.6270(3) 0.9296(2) 0.0630(15) Uani 1 1 d . . . C18 C 0.4432(14) 0.6174(4) 0.9649(3) 0.0706(17) Uani 1 1 d . . . H18A H 0.3864 0.6489 0.9888 0.085 Uiso 1 1 calc R . . C19 C 0.3088(17) 0.5612(4) 0.9656(4) 0.090(3) Uani 1 1 d . . . H19A H 0.1639 0.5551 0.9904 0.108 Uiso 1 1 calc R . . C20 C 0.383(2) 0.5154(4) 0.9313(3) 0.093(3) Uani 1 1 d . . . H20A H 0.2876 0.4782 0.9315 0.112 Uiso 1 1 calc R . . C21 C 0.5976(18) 0.5231(4) 0.8964(3) 0.086(2) Uani 1 1 d . . . H21A H 0.6529 0.4914 0.8725 0.103 Uiso 1 1 calc R . . C22 C 0.7313(15) 0.5784(3) 0.8969(3) 0.0694(17) Uani 1 1 d . . . H22A H 0.8822 0.5832 0.8734 0.083 Uiso 1 1 calc R . . C23 C 0.8454(11) 0.7888(3) 0.8834(2) 0.0591(14) Uani 1 1 d . . . O23 O 1.0255(9) 0.8005(2) 0.9156(2) 0.0721(12) Uani 1 1 d . . . O24 O 0.7658(13) 0.8253(2) 0.8456(3) 0.105(2) Uani 1 1 d D . . H24O H 0.85(2) 0.865(3) 0.851(6) 0.16(5) Uiso 1 1 d D . . C25 C 0.7906(11) 0.4428(3) 0.6178(3) 0.0573(13) Uani 1 1 d . . . O25 O 0.9731(12) 0.4309(2) 0.6494(3) 0.0951(18) Uani 1 1 d . . . O26 O 0.6953(9) 0.4040(2) 0.58181(19) 0.0720(12) Uani 1 1 d D . . H26O H 0.75(2) 0.370(3) 0.606(4) 0.15(4) Uiso 1 1 d D . . C31 C 0.752(3) 0.3644(5) 0.8098(4) 0.16(2) Uiso 0.25 1 d PD . . Cl1 Cl 0.825(3) 0.3617(2) 0.8822(3) 0.144(6) Uani 0.25 1 d PD . . Cl2 Cl 0.945(4) 0.4278(4) 0.7849(3) 0.172(8) Uani 0.25 1 d PD . . Cl3 Cl 0.918(4) 0.2958(5) 0.7883(7) 0.204(9) Uani 0.25 1 d PD . . Cl4 Cl 0.394(3) 0.3528(8) 0.8132(10) 0.228(11) Uani 0.25 1 d PD . . 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 0.067(3) 0.082(4) 0.058(4) -0.006(3) -0.005(3) -0.006(3) C2 0.049(3) 0.069(3) 0.058(3) -0.010(3) -0.001(3) 0.002(2) N3 0.040(2) 0.065(3) 0.054(3) -0.006(2) 0.0002(19) -0.0032(18) C4 0.042(3) 0.062(3) 0.060(3) -0.012(3) -0.008(2) 0.000(2) O4 0.0364(19) 0.118(4) 0.082(3) -0.035(3) -0.0013(19) -0.004(2) C5 0.051(3) 0.067(3) 0.051(3) -0.002(3) -0.004(2) -0.004(2) F5 0.086(2) 0.092(3) 0.069(2) -0.0148(19) 0.024(2) -0.031(2) C6 0.055(3) 0.075(4) 0.047(3) -0.013(3) -0.002(2) 0.000(3) F6 0.076(2) 0.094(2) 0.0558(19) -0.0146(17) -0.0153(17) 0.024(2) C7 0.045(3) 0.077(4) 0.050(3) -0.010(3) -0.007(2) 0.000(2) O7 0.046(2) 0.109(4) 0.070(3) -0.030(2) 0.003(2) -0.004(2) N8 0.043(2) 0.074(3) 0.050(3) -0.006(2) -0.0008(19) 0.002(2) C9 0.052(3) 0.072(3) 0.043(3) -0.005(3) -0.004(2) 0.007(3) C10 0.060(3) 0.076(4) 0.063(4) 0.003(3) 0.014(3) 0.001(3) C11 0.062(3) 0.072(4) 0.050(3) -0.005(3) -0.001(3) -0.005(3) C12 0.085(5) 0.071(4) 0.076(5) 0.009(3) -0.033(4) 0.004(3) C13 0.082(5) 0.096(6) 0.110(6) 0.021(5) -0.037(5) -0.008(4) C14 0.077(4) 0.074(4) 0.104(6) 0.015(4) 0.015(4) 0.001(3) C15 0.102(5) 0.072(4) 0.075(5) -0.005(4) 0.003(4) -0.016(4) C16 0.073(4) 0.069(4) 0.066(4) 0.001(3) 0.001(3) -0.007(3) C17 0.064(3) 0.080(4) 0.045(3) 0.004(3) -0.003(3) 0.002(3) C18 0.064(4) 0.090(4) 0.058(4) 0.006(3) -0.005(3) -0.005(3) C19 0.076(5) 0.116(6) 0.078(5) 0.032(5) -0.011(4) -0.020(4) C20 0.139(7) 0.076(5) 0.066(4) 0.007(4) -0.019(5) -0.012(5) C21 0.113(6) 0.083(5) 0.061(4) 0.005(4) 0.004(4) -0.031(4) C22 0.081(4) 0.069(4) 0.058(3) 0.003(3) 0.009(3) 0.006(3) C23 0.054(3) 0.072(4) 0.052(3) -0.003(3) -0.010(3) -0.001(3) O23 0.066(2) 0.072(3) 0.078(3) -0.006(2) -0.015(2) -0.008(2) O24 0.116(4) 0.076(3) 0.124(4) 0.019(3) -0.060(4) -0.023(3) C25 0.052(3) 0.062(3) 0.058(3) -0.006(3) -0.011(3) 0.009(2) O25 0.099(4) 0.070(3) 0.116(5) -0.011(3) -0.047(3) 0.019(3) O26 0.071(3) 0.078(3) 0.066(3) -0.009(2) -0.020(2) 0.007(2) Cl1 0.353(18) 0.025(2) 0.053(4) 0.011(2) 0.049(7) -0.002(5) Cl2 0.38(2) 0.076(5) 0.059(4) 0.032(4) 0.081(8) 0.077(9) Cl3 0.33(2) 0.072(5) 0.206(14) -0.094(8) 0.125(15) -0.039(9) Cl4 0.33(3) 0.154(13) 0.195(17) 0.051(12) 0.06(2) 0.090(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C17 1.486(10) . ? C1 C2 1.512(9) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N3 1.433(7) . ? C2 C23 1.527(9) . ? C2 H2A 1.0000 . ? N3 C4 1.338(7) . ? N3 H3N 0.9800(11) . ? C4 O4 1.214(7) . ? C4 C5 1.512(9) . ? C5 F5 1.397(7) . ? C5 C6 1.495(10) . ? C5 H5A 1.0000 . ? C6 F6 1.407(7) . ? C6 C7 1.533(8) . ? C6 H6A 1.0000 . ? C7 O7 1.220(7) . ? C7 N8 1.332(7) . ? N8 C9 1.452(7) . ? N8 H8N 0.9800(12) . ? C9 C25 1.493(8) . ? C9 C10 1.531(9) . ? C9 H9A 1.0000 . ? C10 C11 1.476(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.386(9) . ? C11 C16 1.438(9) . ? C12 C13 1.368(12) . ? C12 H12A 0.9500 . ? C13 C14 1.365(13) . ? C13 H13A 0.9500 . ? C14 C15 1.426(12) . ? C14 H14A 0.9500 . ? C15 C16 1.367(10) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 C18 1.385(9) . ? C17 C22 1.386(9) . ? C18 C19 1.409(11) . ? C18 H18A 0.9500 . ? C19 C20 1.363(13) . ? C19 H19A 0.9500 . ? C20 C21 1.374(12) . ? C20 H20A 0.9500 . ? C21 C22 1.391(10) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 O23 1.219(7) . ? C23 O24 1.285(8) . ? O24 H24O 0.980(3) . ? C25 O25 1.220(7) . ? C25 O26 1.313(7) . ? O26 H26O 0.9800(11) . ? C31 Cl1 1.800(5) . ? C31 Cl3 1.800(5) . ? C31 Cl4 1.801(5) . ? C31 Cl2 1.802(5) . ? 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 C1 C2 113.0(5) . . ? C17 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? C17 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? N3 C2 C1 115.2(5) . . ? N3 C2 C23 108.8(5) . . ? C1 C2 C23 112.6(5) . . ? N3 C2 H2A 106.6 . . ? C1 C2 H2A 106.5 . . ? C23 C2 H2A 106.5 . . ? C4 N3 C2 123.4(5) . . ? C4 N3 H3N 125(3) . . ? C2 N3 H3N 110(3) . . ? O4 C4 N3 125.0(5) . . ? O4 C4 C5 118.3(5) . . ? N3 C4 C5 116.7(5) . . ? F5 C5 C6 107.3(5) . . ? F5 C5 C4 111.0(5) . . ? C6 C5 C4 113.5(5) . . ? F5 C5 H5A 108.3 . . ? C6 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? F6 C6 C5 107.9(5) . . ? F6 C6 C7 110.9(5) . . ? C5 C6 C7 112.8(6) . . ? F6 C6 H6A 108.4 . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? O7 C7 N8 126.2(5) . . ? O7 C7 C6 116.8(5) . . ? N8 C7 C6 116.9(5) . . ? C7 N8 C9 122.7(4) . . ? C7 N8 H8N 118(4) . . ? C9 N8 H8N 119(4) . . ? N8 C9 C25 110.2(5) . . ? N8 C9 C10 112.1(5) . . ? C25 C9 C10 110.6(5) . . ? N8 C9 H9A 107.9 . . ? C25 C9 H9A 107.9 . . ? C10 C9 H9A 107.9 . . ? C11 C10 C9 114.6(5) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C16 117.1(6) . . ? C12 C11 C10 122.8(6) . . ? C16 C11 C10 120.0(6) . . ? C13 C12 C11 122.5(7) . . ? C13 C12 H12A 118.7 . . ? C11 C12 H12A 118.7 . . ? C14 C13 C12 120.3(7) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C15 119.9(7) . . ? C13 C14 H14A 120.1 . . ? C15 C14 H14A 120.1 . . ? C16 C15 C14 119.5(7) . . ? C16 C15 H15A 120.2 . . ? C14 C15 H15A 120.2 . . ? C15 C16 C11 120.7(7) . . ? C15 C16 H16A 119.7 . . ? C11 C16 H16A 119.7 . . ? C18 C17 C22 116.3(7) . . ? C18 C17 C1 121.8(6) . . ? C22 C17 C1 121.9(6) . . ? C17 C18 C19 120.6(8) . . ? C17 C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C20 C19 C18 121.0(8) . . ? C20 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? C19 C20 C21 119.9(8) . . ? C19 C20 H20A 120.0 . . ? C21 C20 H20A 120.0 . . ? C20 C21 C22 118.4(8) . . ? C20 C21 H21A 120.8 . . ? C22 C21 H21A 120.8 . . ? C17 C22 C21 123.8(7) . . ? C17 C22 H22A 118.1 . . ? C21 C22 H22A 118.1 . . ? O23 C23 O24 123.7(6) . . ? O23 C23 C2 122.1(6) . . ? O24 C23 C2 114.2(5) . . ? C23 O24 H24O 109(8) . . ? O25 C25 O26 123.3(5) . . ? O25 C25 C9 122.1(5) . . ? O26 C25 C9 114.5(5) . . ? C25 O26 H26O 90(7) . . ? Cl1 C31 Cl3 99.3(6) . . ? Cl1 C31 Cl4 98.7(12) . . ? Cl3 C31 Cl4 110.4(12) . . ? Cl1 C31 Cl2 104.2(6) . . ? Cl3 C31 Cl2 108.1(8) . . ? Cl4 C31 Cl2 130.7(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 C1 C2 N3 -55.6(7) . . . . ? C17 C1 C2 C23 178.7(5) . . . . ? C1 C2 N3 C4 103.9(7) . . . . ? C23 C2 N3 C4 -128.5(6) . . . . ? C2 N3 C4 O4 5.0(10) . . . . ? C2 N3 C4 C5 -176.0(5) . . . . ? O4 C4 C5 F5 155.4(6) . . . . ? N3 C4 C5 F5 -23.8(8) . . . . ? O4 C4 C5 C6 -83.6(7) . . . . ? N3 C4 C5 C6 97.2(6) . . . . ? F5 C5 C6 F6 49.0(6) . . . . ? C4 C5 C6 F6 -74.0(6) . . . . ? F5 C5 C6 C7 -73.9(6) . . . . ? C4 C5 C6 C7 163.1(5) . . . . ? F6 C6 C7 O7 165.6(6) . . . . ? C5 C6 C7 O7 -73.3(8) . . . . ? F6 C6 C7 N8 -12.2(8) . . . . ? C5 C6 C7 N8 109.0(6) . . . . ? O7 C7 N8 C9 1.8(11) . . . . ? C6 C7 N8 C9 179.3(5) . . . . ? C7 N8 C9 C25 -130.5(6) . . . . ? C7 N8 C9 C10 105.9(6) . . . . ? N8 C9 C10 C11 -63.6(7) . . . . ? C25 C9 C10 C11 173.0(5) . . . . ? C9 C10 C11 C12 -90.4(8) . . . . ? C9 C10 C11 C16 84.7(8) . . . . ? C16 C11 C12 C13 1.1(11) . . . . ? C10 C11 C12 C13 176.4(8) . . . . ? C11 C12 C13 C14 -0.1(14) . . . . ? C12 C13 C14 C15 0.0(14) . . . . ? C13 C14 C15 C16 -1.0(12) . . . . ? C14 C15 C16 C11 2.1(10) . . . . ? C12 C11 C16 C15 -2.1(10) . . . . ? C10 C11 C16 C15 -177.5(6) . . . . ? C2 C1 C17 C18 -94.6(7) . . . . ? C2 C1 C17 C22 86.8(8) . . . . ? C22 C17 C18 C19 -1.3(9) . . . . ? C1 C17 C18 C19 -179.9(7) . . . . ? C17 C18 C19 C20 -0.9(11) . . . . ? C18 C19 C20 C21 1.9(12) . . . . ? C19 C20 C21 C22 -0.6(12) . . . . ? C18 C17 C22 C21 2.6(10) . . . . ? C1 C17 C22 C21 -178.8(7) . . . . ? C20 C21 C22 C17 -1.7(12) . . . . ? N3 C2 C23 O23 -129.3(6) . . . . ? C1 C2 C23 O23 -0.3(8) . . . . ? N3 C2 C23 O24 49.4(7) . . . . ? C1 C2 C23 O24 178.4(6) . . . . ? N8 C9 C25 O25 -29.4(8) . . . . ? C10 C9 C25 O25 95.0(8) . . . . ? N8 C9 C25 O26 153.4(5) . . . . ? C10 C9 C25 O26 -82.1(7) . . . . ? 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 N3 H3N O4 0.9800(11) 1.84(2) 2.773(6) 158(5) 1_655 N8 H8N F6 0.9800(12) 2.23(7) 2.655(6) 105(5) . N8 H8N O7 0.9800(12) 2.01(4) 2.863(6) 144(6) 1_655 O24 H24O O25 0.980(3) 1.70(3) 2.671(7) 170(13) 3_756 O26 H26O O23 0.9800(11) 1.98(10) 2.676(6) 126(9) 3_746 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 67.99 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.795 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.114 data_5b _database_code_depnum_ccdc_archive 'CCDC 271258' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 F2 N2 O6' _chemical_formula_sum 'C22 H22 F2 N2 O6' _chemical_formula_weight 448.42 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.121(2) _cell_length_b 6.1323(10) _cell_length_c 30.671(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.179(6) _cell_angle_gamma 90.00 _cell_volume 2091.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4749 _cell_measurement_theta_min 1.9450 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3854 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type ccd _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13463 _diffrn_reflns_av_R_equivalents 0.0887 _diffrn_reflns_av_sigmaI/netI 0.1798 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.34 _reflns_number_total 6970 _reflns_number_gt 4011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0104(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.6(14) _refine_ls_number_reflns 6970 _refine_ls_number_parameters 611 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1584 _refine_ls_R_factor_gt 0.0825 _refine_ls_wR_factor_ref 0.1924 _refine_ls_wR_factor_gt 0.1525 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.094 _refine_ls_shift/su_mean 0.005 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 0.7175(6) 0.4451(11) 0.3754(2) 0.0273(17) Uani 1 1 d . . . H1A H 0.7953 0.3692 0.3715 0.033 Uiso 1 1 calc R . . H1B H 0.7336 0.5834 0.3910 0.033 Uiso 1 1 calc R . . C2 C 0.6650(6) 0.4978(10) 0.3304(2) 0.0212(16) Uani 1 1 d . . . H2A H 0.5911 0.5876 0.3351 0.025 Uiso 1 1 calc R . . N3 N 0.6288(6) 0.3031(9) 0.30663(19) 0.0253(14) Uani 1 1 d D . . H3N H 0.697(5) 0.242(14) 0.291(3) 0.07(3) Uiso 1 1 d D . . C4 C 0.5117(6) 0.2536(11) 0.3007(2) 0.0207(16) Uani 1 1 d . . . O4 O 0.4279(4) 0.3655(7) 0.31469(15) 0.0252(11) Uani 1 1 d . . . C5 C 0.4839(6) 0.0507(11) 0.2748(2) 0.0209(16) Uani 1 1 d . . . H5A H 0.4418 0.0930 0.2472 0.025 Uiso 1 1 calc R . . F5 F 0.5904(3) -0.0612(6) 0.26437(13) 0.0297(10) Uani 1 1 d . . . C6 C 0.4026(6) -0.1038(11) 0.3010(2) 0.0205(16) Uani 1 1 d . . . H6A H 0.4036 -0.2511 0.2871 0.025 Uiso 1 1 calc R . . F6 F 0.4487(3) -0.1209(6) 0.34361(12) 0.0260(9) Uani 1 1 d . . . C7 C 0.2752(6) -0.0175(11) 0.3007(2) 0.0224(16) Uani 1 1 d . . . O7 O 0.2247(4) -0.0017(8) 0.26512(16) 0.0296(12) Uani 1 1 d . . . N8 N 0.2269(5) 0.0404(9) 0.33912(19) 0.0229(14) Uani 1 1 d D . . H8N H 0.271(7) -0.035(15) 0.362(2) 0.09(4) Uiso 1 1 d D . . C9 C 0.1059(6) 0.1286(11) 0.3401(2) 0.0243(17) Uani 1 1 d . . . H9A H 0.0686 0.0929 0.3113 0.029 Uiso 1 1 calc R . . C10 C 0.0277(7) 0.0157(11) 0.3751(2) 0.0282(18) Uani 1 1 d . . . H10A H -0.0527 0.0850 0.3754 0.034 Uiso 1 1 calc R . . H10B H 0.0168 -0.1393 0.3670 0.034 Uiso 1 1 calc R . . C11 C 0.0818(6) 0.0280(11) 0.4206(2) 0.0245(17) Uani 1 1 d . . . C12 C 0.1461(7) -0.1497(12) 0.4367(2) 0.0309(18) Uani 1 1 d . . . H12A H 0.1591 -0.2744 0.4189 0.037 Uiso 1 1 calc R . . C13 C 0.1908(7) -0.1428(13) 0.4786(3) 0.035(2) Uani 1 1 d . . . H13A H 0.2336 -0.2652 0.4896 0.042 Uiso 1 1 calc R . . C14 C 0.1750(7) 0.0388(12) 0.5054(2) 0.0314(18) Uani 1 1 d . . . H14A H 0.2077 0.0425 0.5341 0.038 Uiso 1 1 calc R . . C15 C 0.1100(7) 0.2139(13) 0.4890(3) 0.036(2) Uani 1 1 d . . . H15A H 0.0968 0.3388 0.5067 0.043 Uiso 1 1 calc R . . C16 C 0.0643(7) 0.2078(12) 0.4469(3) 0.0334(19) Uani 1 1 d . . . H16A H 0.0203 0.3290 0.4360 0.040 Uiso 1 1 calc R . . C17 C 0.6355(7) 0.3031(11) 0.4034(2) 0.0265(17) Uani 1 1 d . . . C18 C 0.6735(6) 0.1042(11) 0.4186(3) 0.0275(18) Uani 1 1 d . . . H18A H 0.7509 0.0520 0.4108 0.033 Uiso 1 1 calc R . . C19 C 0.6009(7) -0.0218(13) 0.4452(2) 0.036(2) Uani 1 1 d . . . H19A H 0.6286 -0.1587 0.4557 0.043 Uiso 1 1 calc R . . C20 C 0.4863(7) 0.0538(12) 0.4566(2) 0.0345(19) Uani 1 1 d . . . H20A H 0.4356 -0.0301 0.4749 0.041 Uiso 1 1 calc R . . C21 C 0.4485(7) 0.2532(13) 0.4404(2) 0.0342(19) Uani 1 1 d . . . H21A H 0.3700 0.3036 0.4473 0.041 Uiso 1 1 calc R . . C22 C 0.5214(7) 0.3803(12) 0.4147(2) 0.0321(18) Uani 1 1 d . . . H22A H 0.4946 0.5188 0.4047 0.038 Uiso 1 1 calc R . . C23 C 0.7509(7) 0.6331(11) 0.3031(3) 0.0250(18) Uani 1 1 d . . . O23 O 0.7759(4) 0.5894(7) 0.26504(17) 0.0290(13) Uani 1 1 d . . . O24 O 0.7901(5) 0.8067(7) 0.32384(16) 0.0266(12) Uani 1 1 d D . . H24O H 0.833(10) 0.917(15) 0.307(4) 0.14(5) Uiso 1 1 d D . . C25 C 0.1035(7) 0.3762(11) 0.3441(2) 0.0275(18) Uani 1 1 d . . . O25 O 0.0094(5) 0.4746(8) 0.35159(17) 0.0353(13) Uani 1 1 d . . . O26 O 0.2037(4) 0.4876(7) 0.33620(16) 0.0302(12) Uani 1 1 d D . . H26O H 0.265(4) 0.375(7) 0.3318(19) 0.015(17) Uiso 1 1 d D . . C31 C 0.8321(7) -0.0907(12) 0.1553(2) 0.0325(18) Uani 1 1 d . . . H31A H 0.7679 -0.1814 0.1684 0.039 Uiso 1 1 calc R . . H31B H 0.7938 0.0404 0.1426 0.039 Uiso 1 1 calc R . . C32 C 0.9203(6) -0.0196(11) 0.1915(2) 0.0219(16) Uani 1 1 d . . . H32A H 0.9846 0.0717 0.1779 0.026 Uiso 1 1 calc R . . N33 N 0.9760(5) -0.2046(9) 0.21152(19) 0.0243(14) Uani 1 1 d D . . H33N H 0.930(6) -0.292(10) 0.2323(19) 0.05(2) Uiso 1 1 d D . . C34 C 1.0910(6) -0.2617(11) 0.2032(2) 0.0229(16) Uani 1 1 d . . . O34 O 1.1589(4) -0.1547(7) 0.17961(15) 0.0257(12) Uani 1 1 d . . . C35 C 1.1388(6) -0.4625(10) 0.2261(2) 0.0227(16) Uani 1 1 d . . . H35A H 1.1948 -0.4163 0.2499 0.027 Uiso 1 1 calc R . . F35 F 1.0425(4) -0.5798(6) 0.24449(13) 0.0341(11) Uani 1 1 d . . . C36 C 1.2050(6) -0.6106(11) 0.1952(2) 0.0206(16) Uani 1 1 d . . . H36A H 1.2135 -0.7576 0.2090 0.025 Uiso 1 1 calc R . . F36 F 1.1420(4) -0.6328(6) 0.15614(13) 0.0282(10) Uani 1 1 d . . . C37 C 1.3292(7) -0.5166(11) 0.1876(2) 0.0255(17) Uani 1 1 d . . . O37 O 1.3989(4) -0.4955(8) 0.21808(17) 0.0326(13) Uani 1 1 d . . . N38 N 1.3570(6) -0.4617(9) 0.1461(2) 0.0269(15) Uani 1 1 d D . . H38N H 1.298(6) -0.500(14) 0.124(2) 0.07(3) Uiso 1 1 d D . . C39 C 1.4727(7) -0.3647(10) 0.1348(3) 0.0243(18) Uani 1 1 d . . . H39A H 1.5304 -0.4062 0.1584 0.029 Uiso 1 1 calc R . . C40 C 1.5217(7) -0.4613(12) 0.0925(2) 0.0316(19) Uani 1 1 d . . . H40A H 1.5906 -0.3715 0.0828 0.038 Uiso 1 1 calc R . . H40B H 1.5525 -0.6096 0.0987 0.038 Uiso 1 1 calc R . . C41 C 1.4321(7) -0.4762(12) 0.0553(2) 0.0276(18) Uani 1 1 d . . . C42 C 1.3634(7) -0.6682(11) 0.0488(2) 0.0300(19) Uani 1 1 d . . . H42A H 1.3716 -0.7858 0.0687 0.036 Uiso 1 1 calc R . . C43 C 1.2855(7) -0.6878(12) 0.0144(2) 0.0286(18) Uani 1 1 d . . . H43A H 1.2411 -0.8186 0.0104 0.034 Uiso 1 1 calc R . . C44 C 1.2715(7) -0.5146(13) -0.0148(2) 0.0331(18) Uani 1 1 d . . . H44A H 1.2175 -0.5270 -0.0388 0.040 Uiso 1 1 calc R . . C45 C 1.3365(7) -0.3259(13) -0.0087(3) 0.036(2) Uani 1 1 d . . . H45A H 1.3278 -0.2087 -0.0287 0.044 Uiso 1 1 calc R . . C46 C 1.4142(7) -0.3051(12) 0.0262(3) 0.0306(19) Uani 1 1 d . . . H46A H 1.4561 -0.1718 0.0304 0.037 Uiso 1 1 calc R . . C47 C 0.8937(7) -0.2199(12) 0.1192(2) 0.0301(18) Uani 1 1 d . . . C48 C 0.9887(7) -0.1359(12) 0.0955(2) 0.0307(18) Uani 1 1 d . . . H48A H 1.0170 0.0069 0.1018 0.037 Uiso 1 1 calc R . . C49 C 1.0433(7) -0.2558(15) 0.0628(3) 0.042(2) Uani 1 1 d . . . H49A H 1.1109 -0.1996 0.0477 0.051 Uiso 1 1 calc R . . C50 C 0.9964(8) -0.4621(15) 0.0526(3) 0.045(2) Uani 1 1 d . . . H50A H 1.0296 -0.5429 0.0291 0.055 Uiso 1 1 calc R . . C51 C 0.9040(8) -0.5475(13) 0.0759(3) 0.043(2) Uani 1 1 d . . . H51A H 0.8745 -0.6887 0.0690 0.051 Uiso 1 1 calc R . . C52 C 0.8524(7) -0.4309(12) 0.1098(2) 0.0329(19) Uani 1 1 d . . . H52A H 0.7894 -0.4936 0.1265 0.039 Uiso 1 1 calc R . . C53 C 0.8555(7) 0.1186(10) 0.2257(3) 0.0254(18) Uani 1 1 d . . . O53 O 0.8569(4) 0.0897(7) 0.26465(17) 0.0282(12) Uani 1 1 d . . . O54 O 0.7976(5) 0.2851(7) 0.20713(16) 0.0315(13) Uani 1 1 d D . . H54O H 0.757(9) 0.398(13) 0.224(3) 0.12(4) Uiso 1 1 d D . . C55 C 1.4674(7) -0.1124(12) 0.1341(2) 0.0302(18) Uani 1 1 d . . . O55 O 1.5509(4) -0.0106(8) 0.11965(17) 0.0347(13) Uani 1 1 d . . . O56 O 1.3707(5) -0.0144(7) 0.14939(18) 0.0354(13) Uani 1 1 d D . . H56O H 1.311(4) -0.129(7) 0.1544(19) 0.015(17) 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 C1 0.025(4) 0.028(4) 0.029(5) 0.000(3) 0.004(4) 0.005(3) C2 0.017(4) 0.022(4) 0.024(4) -0.001(3) 0.005(3) 0.002(3) N3 0.031(4) 0.025(3) 0.020(4) 0.000(3) 0.002(3) 0.001(3) C4 0.029(4) 0.016(4) 0.017(4) 0.002(3) 0.004(3) -0.005(3) O4 0.024(3) 0.023(3) 0.029(3) 0.003(2) 0.010(2) -0.001(2) C5 0.009(3) 0.035(4) 0.019(4) 0.000(3) 0.004(3) 0.008(3) F5 0.025(2) 0.026(2) 0.038(3) -0.0059(17) 0.009(2) 0.0027(17) C6 0.020(4) 0.021(4) 0.020(4) -0.004(3) 0.004(3) 0.000(3) F6 0.024(2) 0.029(2) 0.025(2) 0.0012(17) -0.0023(19) 0.0033(17) C7 0.030(4) 0.020(4) 0.017(4) -0.007(3) 0.000(3) -0.003(3) O7 0.032(3) 0.039(3) 0.018(3) -0.003(2) -0.005(2) 0.001(2) N8 0.022(3) 0.028(3) 0.018(4) -0.001(3) -0.002(3) 0.000(3) C9 0.018(4) 0.034(4) 0.021(4) -0.001(3) 0.002(3) 0.005(3) C10 0.026(4) 0.031(4) 0.028(5) -0.002(3) 0.009(4) 0.002(3) C11 0.026(4) 0.028(4) 0.020(4) 0.004(3) 0.006(3) -0.006(3) C12 0.031(4) 0.034(4) 0.028(5) 0.009(3) 0.007(4) -0.002(3) C13 0.034(5) 0.040(5) 0.033(5) 0.012(4) 0.003(4) 0.000(4) C14 0.028(4) 0.041(5) 0.025(5) 0.006(4) -0.003(4) -0.006(3) C15 0.033(5) 0.049(5) 0.026(5) -0.010(4) 0.013(4) -0.015(4) C16 0.037(5) 0.039(5) 0.024(5) -0.001(3) 0.009(4) -0.002(4) C17 0.031(4) 0.025(4) 0.024(4) 0.006(3) -0.003(4) -0.008(3) C18 0.019(4) 0.030(4) 0.033(5) -0.001(3) 0.005(4) -0.005(3) C19 0.033(5) 0.038(5) 0.036(5) 0.006(4) 0.010(4) 0.000(4) C20 0.033(5) 0.042(5) 0.029(5) 0.009(4) 0.001(4) -0.010(4) C21 0.024(4) 0.047(5) 0.032(5) 0.009(4) -0.003(4) -0.006(4) C22 0.031(4) 0.031(4) 0.035(5) -0.006(3) 0.003(4) 0.004(4) C23 0.020(4) 0.023(4) 0.032(5) 0.005(3) 0.005(4) 0.006(3) O23 0.027(3) 0.026(3) 0.034(3) -0.004(2) 0.007(3) -0.004(2) O24 0.035(3) 0.023(3) 0.022(3) -0.003(2) 0.007(2) -0.002(2) C25 0.029(4) 0.021(4) 0.033(5) -0.002(3) 0.007(4) -0.003(4) O25 0.027(3) 0.030(3) 0.048(4) 0.003(2) 0.010(3) 0.002(3) O26 0.026(3) 0.025(3) 0.040(3) -0.003(2) 0.005(3) 0.000(2) C31 0.029(4) 0.041(5) 0.028(5) -0.002(3) -0.001(4) 0.000(3) C32 0.023(4) 0.022(4) 0.021(4) 0.004(3) -0.007(3) 0.004(3) N33 0.024(3) 0.028(3) 0.021(4) -0.001(3) 0.004(3) 0.005(3) C34 0.035(5) 0.017(4) 0.017(4) -0.005(3) -0.006(4) -0.004(3) O34 0.029(3) 0.025(3) 0.024(3) 0.000(2) 0.005(2) -0.001(2) C35 0.031(4) 0.016(4) 0.022(4) 0.001(3) 0.006(3) -0.009(3) F35 0.033(3) 0.036(3) 0.032(3) 0.0030(19) 0.009(2) -0.0032(19) C36 0.015(4) 0.026(4) 0.021(4) 0.003(3) 0.005(3) -0.002(3) F36 0.031(2) 0.024(2) 0.029(3) -0.0006(18) -0.002(2) -0.0010(17) C37 0.033(4) 0.020(4) 0.024(4) -0.002(3) 0.000(4) 0.009(3) O37 0.028(3) 0.038(3) 0.032(3) 0.000(2) -0.005(3) 0.002(2) N38 0.031(4) 0.021(3) 0.029(4) 0.000(3) 0.006(3) 0.005(3) C39 0.027(4) 0.024(4) 0.023(5) -0.006(3) 0.013(4) 0.001(3) C40 0.024(4) 0.041(5) 0.030(5) -0.003(4) 0.004(4) 0.008(3) C41 0.029(4) 0.038(5) 0.016(4) 0.001(3) 0.007(3) 0.007(3) C42 0.030(4) 0.028(4) 0.032(5) 0.003(3) 0.003(4) -0.004(3) C43 0.027(4) 0.031(4) 0.028(5) -0.004(3) -0.003(4) 0.003(3) C44 0.023(4) 0.056(5) 0.020(4) -0.007(4) -0.001(3) 0.004(4) C45 0.036(5) 0.048(5) 0.025(5) 0.002(4) -0.004(4) -0.004(4) C46 0.028(5) 0.038(5) 0.027(5) -0.001(3) 0.013(4) -0.006(3) C47 0.030(4) 0.037(5) 0.023(5) -0.004(3) -0.008(4) 0.006(4) C48 0.030(4) 0.035(4) 0.027(5) 0.008(3) 0.003(4) -0.002(4) C49 0.027(5) 0.067(6) 0.033(5) 0.005(4) 0.007(4) 0.010(4) C50 0.041(5) 0.055(6) 0.041(6) -0.006(4) -0.006(5) 0.014(5) C51 0.050(6) 0.033(5) 0.046(6) -0.011(4) -0.008(5) 0.012(4) C52 0.037(5) 0.031(4) 0.031(5) -0.004(4) -0.005(4) 0.007(4) C53 0.027(5) 0.016(4) 0.033(5) 0.000(3) -0.005(4) 0.006(3) O53 0.031(3) 0.030(3) 0.024(3) 0.003(2) 0.005(3) -0.003(2) O54 0.034(3) 0.029(3) 0.031(3) -0.003(2) 0.005(3) 0.007(2) C55 0.032(5) 0.033(4) 0.026(5) -0.001(3) 0.002(4) -0.005(4) O55 0.029(3) 0.026(3) 0.049(4) 0.000(2) 0.012(3) -0.003(2) O56 0.029(3) 0.020(3) 0.057(4) 0.000(2) 0.010(3) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C17 1.529(9) . ? C1 C2 1.531(10) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N3 1.455(8) . ? C2 C23 1.518(9) . ? C2 H2A 1.0000 . ? N3 C4 1.349(9) . ? N3 H3N 0.9800(13) . ? C4 O4 1.236(8) . ? C4 C5 1.507(9) . ? C5 F5 1.406(7) . ? C5 C6 1.538(9) . ? C5 H5A 1.0000 . ? C6 F6 1.406(7) . ? C6 C7 1.512(9) . ? C6 H6A 1.0000 . ? C7 O7 1.229(8) . ? C7 N8 1.345(8) . ? N8 C9 1.450(9) . ? N8 H8N 0.9800(11) . ? C9 C25 1.523(9) . ? C9 C10 1.546(9) . ? C9 H9A 1.0000 . ? C10 C11 1.521(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.380(10) . ? C11 C12 1.393(10) . ? C12 C13 1.378(10) . ? C12 H12A 0.9500 . ? C13 C14 1.396(10) . ? C13 H13A 0.9500 . ? C14 C15 1.388(11) . ? C14 H14A 0.9500 . ? C15 C16 1.386(11) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 C18 1.373(10) . ? C17 C22 1.399(10) . ? C18 C19 1.385(10) . ? C18 H18A 0.9500 . ? C19 C20 1.401(10) . ? C19 H19A 0.9500 . ? C20 C21 1.384(10) . ? C20 H20A 0.9500 . ? C21 C22 1.375(10) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 O23 1.230(9) . ? C23 O24 1.314(9) . ? O24 H24O 0.9800(11) . ? C25 O25 1.230(8) . ? C25 O26 1.330(8) . ? O26 H26O 0.9800(11) . ? C31 C47 1.526(10) . ? C31 C32 1.541(9) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 N33 1.430(8) . ? C32 C53 1.531(10) . ? C32 H32A 1.0000 . ? N33 C34 1.351(9) . ? N33 H33N 0.9800(12) . ? C34 O34 1.236(8) . ? C34 C35 1.513(9) . ? C35 F35 1.409(7) . ? C35 C36 1.506(9) . ? C35 H35A 1.0000 . ? C36 F36 1.394(8) . ? C36 C37 1.516(9) . ? C36 H36A 1.0000 . ? C37 O37 1.219(8) . ? C37 N38 1.353(9) . ? N38 C39 1.460(9) . ? N38 H38N 0.9800(11) . ? C39 C40 1.529(10) . ? C39 C55 1.549(9) . ? C39 H39A 1.0000 . ? C40 C41 1.514(10) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C46 1.392(10) . ? C41 C42 1.418(10) . ? C42 C43 1.367(10) . ? C42 H42A 0.9500 . ? C43 C44 1.399(10) . ? C43 H43A 0.9500 . ? C44 C45 1.377(10) . ? C44 H44A 0.9500 . ? C45 C46 1.378(11) . ? C45 H45A 0.9500 . ? C46 H46A 0.9500 . ? C47 C48 1.383(10) . ? C47 C52 1.403(11) . ? C48 C49 1.386(10) . ? C48 H48A 0.9500 . ? C49 C50 1.404(12) . ? C49 H49A 0.9500 . ? C50 C51 1.359(11) . ? C50 H50A 0.9500 . ? C51 C52 1.387(10) . ? C51 H51A 0.9500 . ? C52 H52A 0.9500 . ? C53 O53 1.209(9) . ? C53 O54 1.333(8) . ? O54 H54O 0.9800(11) . ? C55 O55 1.205(8) . ? C55 O56 1.320(8) . ? O56 H56O 0.9800(11) . ? 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 C1 C2 113.7(6) . . ? C17 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? C17 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? N3 C2 C23 110.3(6) . . ? N3 C2 C1 112.4(5) . . ? C23 C2 C1 111.9(6) . . ? N3 C2 H2A 107.3 . . ? C23 C2 H2A 107.3 . . ? C1 C2 H2A 107.3 . . ? C4 N3 C2 121.2(6) . . ? C4 N3 H3N 127(5) . . ? C2 N3 H3N 110(5) . . ? O4 C4 N3 123.8(6) . . ? O4 C4 C5 119.2(6) . . ? N3 C4 C5 116.9(6) . . ? F5 C5 C4 110.6(6) . . ? F5 C5 C6 108.4(5) . . ? C4 C5 C6 110.7(5) . . ? F5 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? F6 C6 C7 111.8(5) . . ? F6 C6 C5 108.6(5) . . ? C7 C6 C5 109.5(5) . . ? F6 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? O7 C7 N8 125.0(7) . . ? O7 C7 C6 117.4(6) . . ? N8 C7 C6 117.6(6) . . ? C7 N8 C9 119.4(6) . . ? C7 N8 H8N 108(6) . . ? C9 N8 H8N 128(6) . . ? N8 C9 C25 113.0(6) . . ? N8 C9 C10 111.8(6) . . ? C25 C9 C10 112.4(6) . . ? N8 C9 H9A 106.3 . . ? C25 C9 H9A 106.4 . . ? C10 C9 H9A 106.4 . . ? C11 C10 C9 113.1(6) . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C16 C11 C12 119.4(7) . . ? C16 C11 C10 121.3(6) . . ? C12 C11 C10 119.2(6) . . ? C13 C12 C11 119.3(7) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C12 C13 C14 121.9(7) . . ? C12 C13 H13A 119.0 . . ? C14 C13 H13A 119.0 . . ? C15 C14 C13 118.0(7) . . ? C15 C14 H14A 121.0 . . ? C13 C14 H14A 121.0 . . ? C16 C15 C14 120.4(7) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C11 C16 C15 120.9(7) . . ? C11 C16 H16A 119.5 . . ? C15 C16 H16A 119.5 . . ? C18 C17 C22 119.7(7) . . ? C18 C17 C1 121.0(7) . . ? C22 C17 C1 119.3(6) . . ? C17 C18 C19 121.1(7) . . ? C17 C18 H18A 119.4 . . ? C19 C18 H18A 119.5 . . ? C18 C19 C20 119.6(7) . . ? C18 C19 H19A 120.2 . . ? C20 C19 H19A 120.2 . . ? C21 C20 C19 118.6(7) . . ? C21 C20 H20A 120.7 . . ? C19 C20 H20A 120.7 . . ? C22 C21 C20 121.8(7) . . ? C22 C21 H21A 119.1 . . ? C20 C21 H21A 119.1 . . ? C21 C22 C17 119.1(7) . . ? C21 C22 H22A 120.4 . . ? C17 C22 H22A 120.4 . . ? O23 C23 O24 124.1(6) . . ? O23 C23 C2 123.2(6) . . ? O24 C23 C2 112.6(6) . . ? C23 O24 H24O 118(8) . . ? O25 C25 O26 119.7(6) . . ? O25 C25 C9 121.3(7) . . ? O26 C25 C9 118.8(6) . . ? C25 O26 H26O 104(3) . . ? C47 C31 C32 112.5(6) . . ? C47 C31 H31A 109.1 . . ? C32 C31 H31A 109.1 . . ? C47 C31 H31B 109.1 . . ? C32 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? N33 C32 C53 110.5(5) . . ? N33 C32 C31 111.0(6) . . ? C53 C32 C31 110.4(6) . . ? N33 C32 H32A 108.3 . . ? C53 C32 H32A 108.3 . . ? C31 C32 H32A 108.3 . . ? C34 N33 C32 122.3(6) . . ? C34 N33 H33N 119(5) . . ? C32 N33 H33N 119(5) . . ? O34 C34 N33 123.6(6) . . ? O34 C34 C35 119.3(6) . . ? N33 C34 C35 117.1(6) . . ? F35 C35 C36 108.5(5) . . ? F35 C35 C34 109.6(6) . . ? C36 C35 C34 111.8(6) . . ? F35 C35 H35A 109.0 . . ? C36 C35 H35A 109.0 . . ? C34 C35 H35A 109.0 . . ? F36 C36 C35 110.7(5) . . ? F36 C36 C37 111.1(6) . . ? C35 C36 C37 108.4(6) . . ? F36 C36 H36A 108.9 . . ? C35 C36 H36A 108.9 . . ? C37 C36 H36A 108.9 . . ? O37 C37 N38 123.2(7) . . ? O37 C37 C36 120.0(7) . . ? N38 C37 C36 116.8(7) . . ? C37 N38 C39 122.0(7) . . ? C37 N38 H38N 117(5) . . ? C39 N38 H38N 121(5) . . ? N38 C39 C40 111.2(6) . . ? N38 C39 C55 112.2(6) . . ? C40 C39 C55 112.9(6) . . ? N38 C39 H39A 106.7 . . ? C40 C39 H39A 106.7 . . ? C55 C39 H39A 106.7 . . ? C41 C40 C39 115.3(6) . . ? C41 C40 H40A 108.5 . . ? C39 C40 H40A 108.5 . . ? C41 C40 H40B 108.5 . . ? C39 C40 H40B 108.5 . . ? H40A C40 H40B 107.5 . . ? C46 C41 C42 117.3(7) . . ? C46 C41 C40 122.0(7) . . ? C42 C41 C40 120.7(6) . . ? C43 C42 C41 121.5(7) . . ? C43 C42 H42A 119.3 . . ? C41 C42 H42A 119.3 . . ? C42 C43 C44 119.8(7) . . ? C42 C43 H43A 120.1 . . ? C44 C43 H43A 120.1 . . ? C45 C44 C43 119.5(7) . . ? C45 C44 H44A 120.3 . . ? C43 C44 H44A 120.3 . . ? C46 C45 C44 120.8(7) . . ? C46 C45 H45A 119.6 . . ? C44 C45 H45A 119.6 . . ? C45 C46 C41 121.1(7) . . ? C45 C46 H46A 119.5 . . ? C41 C46 H46A 119.5 . . ? C48 C47 C52 119.0(7) . . ? C48 C47 C31 122.2(7) . . ? C52 C47 C31 118.7(7) . . ? C47 C48 C49 121.3(8) . . ? C47 C48 H48A 119.3 . . ? C49 C48 H48A 119.3 . . ? C48 C49 C50 118.5(8) . . ? C48 C49 H49A 120.8 . . ? C50 C49 H49A 120.8 . . ? C51 C50 C49 120.7(8) . . ? C51 C50 H50A 119.7 . . ? C49 C50 H50A 119.7 . . ? C50 C51 C52 120.8(8) . . ? C50 C51 H51A 119.6 . . ? C52 C51 H51A 119.6 . . ? C51 C52 C47 119.6(8) . . ? C51 C52 H52A 120.2 . . ? C47 C52 H52A 120.2 . . ? O53 C53 O54 122.6(6) . . ? O53 C53 C32 126.3(6) . . ? O54 C53 C32 111.1(6) . . ? C53 O54 H54O 122(7) . . ? O55 C55 O56 121.7(7) . . ? O55 C55 C39 119.6(7) . . ? O56 C55 C39 118.8(6) . . ? C55 O56 H56O 107(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 C1 C2 N3 -53.5(8) . . . . ? C17 C1 C2 C23 -178.2(6) . . . . ? C23 C2 N3 C4 -126.5(6) . . . . ? C1 C2 N3 C4 107.8(7) . . . . ? C2 N3 C4 O4 -0.4(10) . . . . ? C2 N3 C4 C5 178.7(6) . . . . ? O4 C4 C5 F5 -176.1(6) . . . . ? N3 C4 C5 F5 4.8(8) . . . . ? O4 C4 C5 C6 -55.9(8) . . . . ? N3 C4 C5 C6 124.9(6) . . . . ? F5 C5 C6 F6 75.2(6) . . . . ? C4 C5 C6 F6 -46.2(7) . . . . ? F5 C5 C6 C7 -162.5(5) . . . . ? C4 C5 C6 C7 76.0(7) . . . . ? F6 C6 C7 O7 -178.0(5) . . . . ? C5 C6 C7 O7 61.7(7) . . . . ? F6 C6 C7 N8 3.4(8) . . . . ? C5 C6 C7 N8 -116.9(6) . . . . ? O7 C7 N8 C9 0.1(10) . . . . ? C6 C7 N8 C9 178.6(6) . . . . ? C7 N8 C9 C25 -100.7(8) . . . . ? C7 N8 C9 C10 131.3(6) . . . . ? N8 C9 C10 C11 56.4(8) . . . . ? C25 C9 C10 C11 -71.9(8) . . . . ? C9 C10 C11 C16 84.4(8) . . . . ? C9 C10 C11 C12 -98.2(7) . . . . ? C16 C11 C12 C13 0.2(10) . . . . ? C10 C11 C12 C13 -177.2(6) . . . . ? C11 C12 C13 C14 -0.9(11) . . . . ? C12 C13 C14 C15 1.3(11) . . . . ? C13 C14 C15 C16 -1.0(11) . . . . ? C12 C11 C16 C15 0.1(11) . . . . ? C10 C11 C16 C15 177.5(7) . . . . ? C14 C15 C16 C11 0.3(11) . . . . ? C2 C1 C17 C18 121.0(7) . . . . ? C2 C1 C17 C22 -60.9(9) . . . . ? C22 C17 C18 C19 -0.2(11) . . . . ? C1 C17 C18 C19 177.9(7) . . . . ? C17 C18 C19 C20 0.5(12) . . . . ? C18 C19 C20 C21 0.5(11) . . . . ? C19 C20 C21 C22 -1.8(12) . . . . ? C20 C21 C22 C17 2.0(12) . . . . ? C18 C17 C22 C21 -1.0(11) . . . . ? C1 C17 C22 C21 -179.2(7) . . . . ? N3 C2 C23 O23 5.9(9) . . . . ? C1 C2 C23 O23 131.9(7) . . . . ? N3 C2 C23 O24 -177.4(6) . . . . ? C1 C2 C23 O24 -51.5(7) . . . . ? N8 C9 C25 O25 -169.6(7) . . . . ? C10 C9 C25 O25 -41.9(11) . . . . ? N8 C9 C25 O26 15.2(10) . . . . ? C10 C9 C25 O26 143.0(6) . . . . ? C47 C31 C32 N33 -60.0(8) . . . . ? C47 C31 C32 C53 177.2(6) . . . . ? C53 C32 N33 C34 -132.5(7) . . . . ? C31 C32 N33 C34 104.7(7) . . . . ? C32 N33 C34 O34 3.7(10) . . . . ? C32 N33 C34 C35 -179.3(6) . . . . ? O34 C34 C35 F35 -169.4(6) . . . . ? N33 C34 C35 F35 13.4(8) . . . . ? O34 C34 C35 C36 -49.1(8) . . . . ? N33 C34 C35 C36 133.7(6) . . . . ? F35 C35 C36 F36 77.1(6) . . . . ? C34 C35 C36 F36 -43.9(7) . . . . ? F35 C35 C36 C37 -160.8(6) . . . . ? C34 C35 C36 C37 78.3(7) . . . . ? F36 C36 C37 O37 -176.6(6) . . . . ? C35 C36 C37 O37 61.5(8) . . . . ? F36 C36 C37 N38 2.7(8) . . . . ? C35 C36 C37 N38 -119.1(7) . . . . ? O37 C37 N38 C39 -2.2(10) . . . . ? C36 C37 N38 C39 178.5(6) . . . . ? C37 N38 C39 C40 138.7(7) . . . . ? C37 N38 C39 C55 -93.8(8) . . . . ? N38 C39 C40 C41 46.8(8) . . . . ? C55 C39 C40 C41 -80.3(8) . . . . ? C39 C40 C41 C46 88.2(8) . . . . ? C39 C40 C41 C42 -92.3(8) . . . . ? C46 C41 C42 C43 2.2(10) . . . . ? C40 C41 C42 C43 -177.4(6) . . . . ? C41 C42 C43 C44 -0.8(11) . . . . ? C42 C43 C44 C45 0.0(11) . . . . ? C43 C44 C45 C46 -0.7(11) . . . . ? C44 C45 C46 C41 2.2(11) . . . . ? C42 C41 C46 C45 -2.8(10) . . . . ? C40 C41 C46 C45 176.7(6) . . . . ? C32 C31 C47 C48 -57.7(9) . . . . ? C32 C31 C47 C52 122.3(7) . . . . ? C52 C47 C48 C49 0.0(11) . . . . ? C31 C47 C48 C49 -179.9(7) . . . . ? C47 C48 C49 C50 3.1(11) . . . . ? C48 C49 C50 C51 -3.8(12) . . . . ? C49 C50 C51 C52 1.4(13) . . . . ? C50 C51 C52 C47 1.8(12) . . . . ? C48 C47 C52 C51 -2.5(11) . . . . ? C31 C47 C52 C51 177.4(7) . . . . ? N33 C32 C53 O53 5.3(10) . . . . ? C31 C32 C53 O53 128.4(8) . . . . ? N33 C32 C53 O54 -176.6(6) . . . . ? C31 C32 C53 O54 -53.4(8) . . . . ? N38 C39 C55 O55 -170.0(7) . . . . ? C40 C39 C55 O55 -43.4(10) . . . . ? N38 C39 C55 O56 9.7(10) . . . . ? C40 C39 C55 O56 136.3(7) . . . . ? 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 N3 H3N O53 0.9800(13) 2.161(16) 3.135(8) 172(8) . N8 H8N F6 0.9800(11) 2.13(9) 2.661(7) 112(7) . O24 H24O O53 0.9800(11) 1.69(5) 2.620(7) 157(12) 1_565 O26 H26O O4 0.9800(11) 1.89(4) 2.687(7) 137(5) . O26 H26O N8 0.9800(11) 2.11(5) 2.756(7) 122(4) . N33 H33N O23 0.9800(12) 2.12(3) 3.044(8) 157(7) 1_545 N38 H38N F36 0.9800(11) 2.16(9) 2.630(7) 108(6) . O54 H54O O23 0.9800(11) 1.73(7) 2.588(7) 144(10) . O56 H56O O34 0.9800(11) 1.87(4) 2.676(7) 138(5) . O56 H56O N38 0.9800(11) 2.12(5) 2.749(7) 120(4) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.338 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.080