# ol9908880.cif data_shelxl _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H21 N3 O6' _chemical_formula_weight 447.44 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0492 0.0322 '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' _symmetry_cell_setting P 21/n _symmetry_space_group_name_H-M loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.439(2) _cell_length_b 13.539(8) _cell_length_c 21.216(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.795(15) _cell_angle_gamma 90.00 _cell_volume 2135.8(16) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method ? _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.845 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54060 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8037 _diffrn_reflns_av_R_equivalents 0.0957 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 47.90 _reflns_number_total 1655 _reflns_number_observed 1557 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1192P)^2^+1.1282P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0326(32) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1655 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_obs 0.0666 _refine_ls_wR_factor_all 0.1908 _refine_ls_wR_factor_obs 0.1766 _refine_ls_goodness_of_fit_all 1.223 _refine_ls_goodness_of_fit_obs 1.174 _refine_ls_restrained_S_all 1.223 _refine_ls_restrained_S_obs 1.174 _refine_ls_shift/esd_max -0.004 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2816(5) 0.1748(3) 0.65167(15) 0.0696(12) Uani 1 d . . O2 O 0.3827(6) 0.0226(3) 0.6387(2) 0.0881(14) Uani 1 d . . O3 O 0.7984(5) 0.1593(3) 0.7832(2) 0.0781(13) Uani 1 d . . O4 O 0.3532(6) 0.3814(2) 0.74258(15) 0.0629(12) Uani 1 d . . O5 O 0.7496(5) 0.2967(2) 0.63826(13) 0.0486(11) Uani 1 d . . O6 O 0.1465(6) 0.3066(3) 0.4377(2) 0.0844(14) Uani 1 d . . N1 N 0.5438(8) 0.2526(3) 0.7627(2) 0.0517(13) Uani 1 d . . N2 N 0.2350(5) 0.1940(3) 0.5129(2) 0.0542(13) Uani 1 d . . H2 H 0.2629(5) 0.1903(3) 0.5525(2) 0.065 Uiso 1 calc R . N3 N 0.2573(6) 0.0260(3) 0.5177(2) 0.0623(14) Uani 1 d . . C1 C 0.3523(8) 0.1010(4) 0.6734(2) 0.058(2) Uani 1 d . . C2 C 0.4089(8) 0.0872(4) 0.7405(2) 0.071(2) Uani 1 d . . H2A H 0.5291(8) 0.0594(4) 0.7420(2) 0.085 Uiso 1 calc R . H2B H 0.3294(8) 0.0392(4) 0.7590(2) 0.085 Uiso 1 calc R . C3 C 0.4097(8) 0.1794(4) 0.7810(2) 0.067(2) Uani 1 d . . H3A H 0.2914(8) 0.2094(4) 0.7783(2) 0.080 Uiso 1 calc R . H3B H 0.4336(8) 0.1606(4) 0.8246(2) 0.080 Uiso 1 calc R . C4 C 0.7244(11) 0.2371(3) 0.7656(2) 0.056(2) Uani 1 d . . C5 C 0.8249(7) 0.3269(3) 0.7421(2) 0.0498(14) Uani 1 d . . H5 H 0.9101(7) 0.3551(3) 0.7733(2) 0.060 Uiso 1 calc R . C6 C 0.6721(7) 0.3977(3) 0.7218(2) 0.0446(14) Uani 1 d . . H6 H 0.6874(7) 0.4637(3) 0.7400(2) 0.054 Uiso 1 calc R . C7 C 0.5060(10) 0.3483(3) 0.7424(2) 0.050(2) Uani 1 d . . C8 C 0.9092(7) 0.3029(3) 0.6780(2) 0.053(2) Uani 1 d . . H8 H 0.9863(7) 0.2442(3) 0.6780(2) 0.064 Uiso 1 calc R . C9 C 0.9953(8) 0.3962(4) 0.6545(2) 0.055(2) Uani 1 d . . H9 H 1.1176(8) 0.4100(4) 0.6532(2) 0.066 Uiso 1 calc R . C10 C 0.8599(8) 0.4548(4) 0.6359(2) 0.0497(15) Uani 1 d . . H10 H 0.8686(8) 0.5181(4) 0.6192(2) 0.060 Uiso 1 calc R . C11 C 0.6888(7) 0.3975(3) 0.6476(2) 0.0410(14) Uani 1 d . . C12 C 0.5272(6) 0.4200(3) 0.6073(2) 0.0399(13) Uani 1 d . . C13 C 0.4604(7) 0.5167(3) 0.6024(2) 0.0510(15) Uani 1 d . . H13 H 0.5115(7) 0.5667(3) 0.6271(2) 0.061 Uiso 1 calc R . C14 C 0.3186(8) 0.5373(3) 0.5610(2) 0.0550(15) Uani 1 d . . H14 H 0.2758(8) 0.6017(3) 0.5577(2) 0.066 Uiso 1 calc R . C15 C 0.2394(7) 0.4643(4) 0.5243(2) 0.0534(15) Uani 1 d . . H15 H 0.1450(7) 0.4796(4) 0.4962(2) 0.064 Uiso 1 calc R . C16 C 0.3020(7) 0.3666(3) 0.5296(2) 0.0472(14) Uani 1 d . . C17 C 0.4437(7) 0.3466(3) 0.5711(2) 0.0441(14) Uani 1 d . . H17 H 0.4848(7) 0.2820(3) 0.5750(2) 0.053 Uiso 1 calc R . C18 C 0.2180(7) 0.2879(3) 0.4886(2) 0.0536(15) Uani 1 d . . C19 C 0.2126(7) 0.1035(4) 0.4813(2) 0.059(2) Uani 1 d . . C20 C 0.1545(8) 0.0951(4) 0.4185(2) 0.074(2) Uani 1 d . . H20 H 0.1250(8) 0.1505(4) 0.3944(2) 0.088 Uiso 1 calc R . C21 C 0.1427(9) 0.0012(5) 0.3936(3) 0.094(2) Uani 1 d . . H21 H 0.1037(9) -0.0075(5) 0.3519(3) 0.112 Uiso 1 calc R . C22 C 0.1878(9) -0.0795(5) 0.4298(3) 0.094(2) Uani 1 d . . H22 H 0.1826(9) -0.1426(5) 0.4125(3) 0.113 Uiso 1 calc R . C23 C 0.2411(8) -0.0664(4) 0.4921(3) 0.075(2) Uani 1 d . . C24 C 0.2934(9) -0.1501(4) 0.5358(3) 0.098(2) Uani 1 d . . H24A H 0.3257(9) -0.1242(4) 0.5768(3) 0.117 Uiso 1 calc R . H24B H 0.3941(9) -0.1849(4) 0.5193(3) 0.117 Uiso 1 calc R . H24C H 0.1937(9) -0.1947(4) 0.5393(3) 0.117 Uiso 1 calc R . H25 H 0.3479(102) 0.0348(53) 0.5847(42) 0.147(26) Uiso 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 O1 0.094(3) 0.057(2) 0.057(2) 0.006(2) -0.009(2) 0.014(2) O2 0.118(4) 0.055(2) 0.090(3) 0.000(2) -0.008(2) 0.020(2) O3 0.085(3) 0.061(2) 0.087(3) 0.022(2) -0.015(2) 0.007(2) O4 0.059(4) 0.066(2) 0.064(2) 0.007(2) 0.007(2) 0.008(2) O5 0.054(3) 0.041(2) 0.051(2) -0.0085(13) -0.011(2) 0.0076(14) O6 0.111(4) 0.082(3) 0.058(3) 0.005(2) -0.037(2) -0.013(2) N1 0.043(4) 0.057(3) 0.054(2) 0.012(2) -0.007(2) 0.008(3) N2 0.066(4) 0.054(3) 0.042(2) -0.003(2) -0.006(2) -0.010(2) N3 0.059(4) 0.054(3) 0.074(3) -0.015(2) 0.009(2) -0.003(2) C1 0.059(4) 0.048(3) 0.067(4) 0.012(3) 0.001(3) -0.002(3) C2 0.078(5) 0.060(3) 0.074(4) 0.024(3) -0.018(3) -0.012(3) C3 0.081(5) 0.066(3) 0.054(3) 0.022(3) 0.003(3) -0.013(3) C4 0.077(6) 0.044(4) 0.046(3) 0.009(2) -0.005(3) 0.007(3) C5 0.057(4) 0.047(3) 0.045(3) -0.003(2) -0.011(2) 0.005(3) C6 0.053(4) 0.041(3) 0.039(3) -0.002(2) -0.001(2) -0.005(3) C7 0.057(6) 0.055(3) 0.038(3) -0.002(2) -0.002(3) 0.015(4) C8 0.060(5) 0.049(3) 0.051(3) -0.005(2) -0.008(3) 0.006(2) C9 0.044(5) 0.077(4) 0.043(3) -0.013(2) -0.006(2) -0.004(3) C10 0.049(5) 0.058(3) 0.042(3) -0.004(2) 0.000(3) -0.007(3) C11 0.049(4) 0.032(3) 0.042(3) -0.005(2) -0.003(2) 0.002(2) C12 0.043(4) 0.037(3) 0.040(3) 0.003(2) 0.000(2) 0.002(2) C13 0.056(4) 0.045(3) 0.052(3) 0.000(2) 0.000(3) -0.006(3) C14 0.063(5) 0.043(3) 0.059(3) 0.005(2) 0.001(3) 0.002(3) C15 0.053(4) 0.061(4) 0.046(3) 0.016(2) 0.002(2) 0.009(3) C16 0.050(4) 0.055(3) 0.036(3) 0.008(2) 0.001(3) 0.000(3) C17 0.054(4) 0.041(3) 0.038(3) 0.004(2) 0.002(3) 0.001(2) C18 0.053(4) 0.064(4) 0.043(3) 0.001(3) -0.010(3) -0.008(3) C19 0.065(4) 0.060(4) 0.053(3) -0.012(3) 0.008(3) -0.011(3) C20 0.081(5) 0.086(4) 0.055(4) -0.015(3) 0.009(3) -0.021(3) C21 0.118(7) 0.098(5) 0.065(4) -0.028(4) 0.016(4) -0.030(4) C22 0.111(6) 0.084(5) 0.089(5) -0.047(4) 0.032(4) -0.025(4) C23 0.065(5) 0.057(4) 0.104(5) -0.022(4) 0.029(3) -0.004(3) C24 0.099(6) 0.061(4) 0.135(6) -0.022(4) 0.021(4) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.214(6) . ? O2 C1 1.315(6) . ? O3 C4 1.241(6) . ? O4 C7 1.222(6) . ? O5 C8 1.438(6) . ? O5 C11 1.454(5) . ? O6 C18 1.215(5) . ? N1 C4 1.359(7) . ? N1 C7 1.392(6) . ? N1 C3 1.467(7) . ? N2 C18 1.377(6) . ? N2 C19 1.404(6) . ? N3 C19 1.339(6) . ? N3 C23 1.368(6) . ? C1 C2 1.483(7) . ? C2 C3 1.515(7) . ? C4 C5 1.520(7) . ? C5 C6 1.538(7) . ? C5 C8 1.549(7) . ? C6 C7 1.483(8) . ? C6 C11 1.583(6) . ? C8 C9 1.508(7) . ? C9 C10 1.332(7) . ? C10 C11 1.518(7) . ? C11 C12 1.486(6) . ? C12 C17 1.389(6) . ? C12 C13 1.403(6) . ? C13 C14 1.381(7) . ? C14 C15 1.380(7) . ? C15 C16 1.406(7) . ? C16 C17 1.379(6) . ? C16 C18 1.499(7) . ? C19 C20 1.392(7) . ? C20 C21 1.379(8) . ? C21 C22 1.371(9) . ? C22 C23 1.380(9) . ? C23 C24 1.508(9) . ? 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 C8 O5 C11 96.8(3) . . ? C4 N1 C7 110.3(5) . . ? C4 N1 C3 124.3(4) . . ? C7 N1 C3 125.4(6) . . ? C18 N2 C19 128.3(4) . . ? C19 N3 C23 118.0(4) . . ? O1 C1 O2 122.1(5) . . ? O1 C1 C2 125.1(5) . . ? O2 C1 C2 112.8(5) . . ? C1 C2 C3 116.0(4) . . ? N1 C3 C2 113.3(4) . . ? O3 C4 N1 125.0(5) . . ? O3 C4 C5 124.0(7) . . ? N1 C4 C5 111.0(5) . . ? C4 C5 C6 102.9(5) . . ? C4 C5 C8 109.7(4) . . ? C6 C5 C8 101.6(3) . . ? C7 C6 C5 104.6(4) . . ? C7 C6 C11 112.7(4) . . ? C5 C6 C11 101.4(3) . . ? O4 C7 N1 121.3(5) . . ? O4 C7 C6 128.3(4) . . ? N1 C7 C6 110.4(5) . . ? O5 C8 C9 101.9(4) . . ? O5 C8 C5 100.2(4) . . ? C9 C8 C5 107.6(3) . . ? C10 C9 C8 105.8(5) . . ? C9 C10 C11 106.1(4) . . ? O5 C11 C12 111.3(3) . . ? O5 C11 C10 101.1(4) . . ? C12 C11 C10 118.0(4) . . ? O5 C11 C6 99.8(3) . . ? C12 C11 C6 119.0(4) . . ? C10 C11 C6 104.7(3) . . ? C17 C12 C13 118.4(4) . . ? C17 C12 C11 120.8(4) . . ? C13 C12 C11 120.7(4) . . ? C14 C13 C12 119.8(4) . . ? C15 C14 C13 121.2(4) . . ? C14 C15 C16 119.7(5) . . ? C17 C16 C15 118.7(4) . . ? C17 C16 C18 121.9(4) . . ? C15 C16 C18 119.4(5) . . ? C16 C17 C12 122.1(4) . . ? O6 C18 N2 123.9(4) . . ? O6 C18 C16 122.1(4) . . ? N2 C18 C16 114.0(4) . . ? N3 C19 C20 123.6(4) . . ? N3 C19 N2 112.6(4) . . ? C20 C19 N2 123.8(5) . . ? C21 C20 C19 117.1(6) . . ? C22 C21 C20 120.6(6) . . ? C21 C22 C23 119.5(5) . . ? N3 C23 C22 121.1(6) . . ? N3 C23 C24 115.2(5) . . ? C22 C23 C24 123.6(5) . . ? _refine_diff_density_max 0.423 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.146